#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:51:43 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179767 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/63/7006327.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7006327
loop_
_publ_author_name
'Paluch, Marta'
'Lisowski, Jerzy'
'Lis, Tadeusz'
_publ_section_title
;
 Lanthanide complexes of chiral 3 + 3 macrocycles derived from
 (1R,2R)-1,2-diaminocyclohexane and 2,6-diformyl-4-methylphenol.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              381
_journal_page_last               388
_journal_paper_doi               10.1039/b502863a
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C45 H54 N6 O3'
_chemical_formula_sum            'C45 H54 N6 O3'
_chemical_formula_weight         726.94
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.56(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.650(4)
_cell_length_b                   18.789(4)
_cell_length_c                   14.803(4)
_cell_measurement_temperature    100(2)
_cell_volume                     4070.6(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Xcalibur PX CrysAlis CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_sigmaI/netI    0.1338
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26181
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         3.80
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parralelepiped
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_coef       0.00092(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     988
_refine_ls_number_reflns         11185
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0586P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1521
_reflns_number_gt                6383
_reflns_number_total             11185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b502863a.txt
_cod_data_source_block           MACROCYCLE
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7006327
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0013(3) 0.88231(19) 0.2414(3) 0.0316(9) Uani 1 1 d . . .
H01 H 0.0328 0.8972 0.2013 0.047 Uiso 1 1 calc R . .
O2 O -0.2033(2) 0.83377(19) -0.0963(3) 0.0350(10) Uani 1 1 d . . .
H2 H -0.2596 0.8255 -0.1016 0.053 Uiso 1 1 calc R . .
O3 O -0.3738(3) 0.79927(19) 0.2556(2) 0.0315(9) Uani 1 1 d . . .
H03 H -0.3644 0.8113 0.3099 0.047 Uiso 1 1 calc R . .
N1 N 0.1256(3) 0.8725(2) 0.1230(3) 0.0262(10) Uani 1 1 d . . .
N2 N 0.0746(3) 0.8416(2) -0.0634(3) 0.0261(10) Uani 1 1 d . . .
N3 N -0.3537(3) 0.7616(2) -0.1308(3) 0.0308(11) Uani 1 1 d . . .
N4 N -0.4664(3) 0.7152(2) 0.0147(3) 0.0324(11) Uani 1 1 d . . .
N5 N -0.3144(3) 0.7818(2) 0.4222(3) 0.0324(11) Uani 1 1 d . . .
N6 N -0.1227(3) 0.8068(2) 0.4635(3) 0.0291(11) Uani 1 1 d . . .
C1 C -0.0844(4) 0.8302(3) 0.3924(4) 0.0292(12) Uani 1 1 d . . .
H1 H -0.1056 0.8734 0.3655 0.035 Uiso 1 1 calc R . .
C2 C -0.0090(3) 0.7919(3) 0.3521(3) 0.0248(12) Uani 1 1 d . . .
C3 C 0.0240(4) 0.7273(3) 0.3875(4) 0.0287(13) Uani 1 1 d . . .
H3 H -0.0031 0.7078 0.4390 0.034 Uiso 1 1 calc R . .
C4 C 0.0962(4) 0.6905(3) 0.3489(3) 0.0243(12) Uani 1 1 d . . .
C5 C 0.1317(4) 0.6214(3) 0.3866(4) 0.0364(14) Uani 1 1 d . . .
H5A H 0.1549 0.5923 0.3377 0.055 Uiso 1 1 calc R . .
H5B H 0.0821 0.5959 0.4150 0.055 Uiso 1 1 calc R . .
H5C H 0.1811 0.6307 0.4318 0.055 Uiso 1 1 calc R . .
C6 C 0.1339(4) 0.7201(3) 0.2731(3) 0.0256(12) Uani 1 1 d . . .
H6 H 0.1824 0.6960 0.2456 0.031 Uiso 1 1 calc R . .
C7 C 0.1023(4) 0.7842(3) 0.2363(3) 0.0239(11) Uani 1 1 d . . .
C8 C 0.0318(4) 0.8192(3) 0.2749(4) 0.0288(12) Uani 1 1 d . . .
C9 C 0.1469(3) 0.8121(3) 0.1572(4) 0.0270(12) Uani 1 1 d . . .
H9 H 0.1929 0.7846 0.1307 0.032 Uiso 1 1 calc R . .
C10 C 0.1771(3) 0.8992(3) 0.0471(3) 0.0234(11) Uani 1 1 d . . .
H10 H 0.2246 0.8633 0.0325 0.028 Uiso 1 1 calc R . .
C11 C 0.2241(4) 0.9683(3) 0.0749(4) 0.0287(13) Uani 1 1 d . . .
H11A H 0.2669 0.9593 0.1273 0.034 Uiso 1 1 calc R . .
H11B H 0.1778 1.0029 0.0939 0.034 Uiso 1 1 calc R . .
C12 C 0.2766(4) 1.0000(3) -0.0024(4) 0.0354(14) Uani 1 1 d . . .
H12A H 0.3038 1.0461 0.0167 0.042 Uiso 1 1 calc R . .
H12B H 0.3269 0.9675 -0.0178 0.042 Uiso 1 1 calc R . .
C13 C 0.2138(4) 1.0106(3) -0.0833(4) 0.0340(13) Uani 1 1 d . . .
H13A H 0.2487 1.0291 -0.1340 0.041 Uiso 1 1 calc R . .
H13B H 0.1667 1.0463 -0.0693 0.041 Uiso 1 1 calc R . .
C14 C 0.1679(4) 0.9411(3) -0.1109(4) 0.0270(12) Uani 1 1 d . . .
H14A H 0.2150 0.9065 -0.1282 0.032 Uiso 1 1 calc R . .
H14B H 0.1264 0.9495 -0.1645 0.032 Uiso 1 1 calc R . .
C15 C 0.1137(3) 0.9099(3) -0.0353(3) 0.0241(12) Uani 1 1 d . . .
H15 H 0.0636 0.9434 -0.0202 0.029 Uiso 1 1 calc R . .
C16 C -0.0137(4) 0.8391(3) -0.0749(3) 0.0265(12) Uani 1 1 d . . .
H16 H -0.0485 0.8807 -0.0643 0.032 Uiso 1 1 calc R . .
C17 C -0.0610(4) 0.7738(3) -0.1040(4) 0.0256(12) Uani 1 1 d . . .
C18 C -0.0141(4) 0.7115(3) -0.1230(3) 0.0271(12) Uani 1 1 d . . .
H18 H 0.0507 0.7117 -0.1179 0.033 Uiso 1 1 calc R . .
C19 C -0.0585(4) 0.6495(3) -0.1491(3) 0.0254(12) Uani 1 1 d . . .
C20 C -0.0053(4) 0.5815(3) -0.1661(4) 0.0360(14) Uani 1 1 d . . .
H20A H 0.0568 0.5936 -0.1825 0.054 Uiso 1 1 calc R . .
H20B H -0.0360 0.5548 -0.2156 0.054 Uiso 1 1 calc R . .
H20C H -0.0027 0.5523 -0.1112 0.054 Uiso 1 1 calc R . .
C21 C -0.1526(4) 0.6495(3) -0.1538(4) 0.0323(13) Uani 1 1 d . . .
H21 H -0.1842 0.6069 -0.1699 0.039 Uiso 1 1 calc R . .
C22 C -0.2029(4) 0.7108(3) -0.1356(4) 0.0266(12) Uani 1 1 d . . .
C23 C -0.1562(4) 0.7731(3) -0.1119(4) 0.0296(13) Uani 1 1 d . . .
C24 C -0.3012(4) 0.7068(3) -0.1417(4) 0.0307(13) Uani 1 1 d . . .
H24 H -0.3290 0.6620 -0.1544 0.037 Uiso 1 1 calc R . .
C25 C -0.4530(4) 0.7503(3) -0.1420(4) 0.0296(12) Uani 1 1 d . . .
H25 H -0.4647 0.6995 -0.1588 0.035 Uiso 1 1 calc R . .
C26 C -0.4905(4) 0.7978(3) -0.2187(4) 0.0344(14) Uani 1 1 d . . .
H26A H -0.4766 0.8481 -0.2040 0.041 Uiso 1 1 calc R . .
H26B H -0.4599 0.7857 -0.2750 0.041 Uiso 1 1 calc R . .
C27 C -0.5934(4) 0.7887(3) -0.2339(4) 0.0357(14) Uani 1 1 d . . .
H27A H -0.6161 0.8221 -0.2814 0.043 Uiso 1 1 calc R . .
H27B H -0.6068 0.7396 -0.2551 0.043 Uiso 1 1 calc R . .
C28 C -0.6421(4) 0.8025(3) -0.1477(4) 0.0396(15) Uani 1 1 d . . .
H28A H -0.6354 0.8533 -0.1309 0.048 Uiso 1 1 calc R . .
H28B H -0.7081 0.7923 -0.1578 0.048 Uiso 1 1 calc R . .
C29 C -0.6034(4) 0.7566(3) -0.0715(4) 0.0331(13) Uani 1 1 d . . .
H29A H -0.6163 0.7060 -0.0859 0.040 Uiso 1 1 calc R . .
H29B H -0.6347 0.7684 -0.0155 0.040 Uiso 1 1 calc R . .
C30 C -0.4995(3) 0.7663(3) -0.0543(4) 0.0290(13) Uani 1 1 d . . .
H30 H -0.4856 0.8160 -0.0340 0.035 Uiso 1 1 calc R . .
C31 C -0.4386(3) 0.7418(3) 0.0914(4) 0.0284(12) Uani 1 1 d . . .
H31 H -0.4362 0.7921 0.0984 0.034 Uiso 1 1 calc R . .
C32 C -0.4105(4) 0.6960(3) 0.1682(4) 0.0282(12) Uani 1 1 d . . .
C33 C -0.4193(4) 0.6224(3) 0.1634(4) 0.0285(12) Uani 1 1 d . . .
H33 H -0.4419 0.6016 0.1084 0.034 Uiso 1 1 calc R . .
C34 C -0.3964(4) 0.5781(3) 0.2363(4) 0.0298(13) Uani 1 1 d . . .
C35 C -0.4127(4) 0.4985(3) 0.2291(4) 0.0392(15) Uani 1 1 d . . .
H35A H -0.3551 0.4732 0.2425 0.059 Uiso 1 1 calc R . .
H35B H -0.4355 0.4867 0.1677 0.059 Uiso 1 1 calc R . .
H35C H -0.4578 0.4841 0.2725 0.059 Uiso 1 1 calc R . .
C36 C -0.3628(3) 0.6094(3) 0.3151(4) 0.0285(13) Uani 1 1 d . . .
H36 H -0.3458 0.5800 0.3653 0.034 Uiso 1 1 calc R . .
C37 C -0.3530(4) 0.6836(3) 0.3234(4) 0.0266(12) Uani 1 1 d . . .
C38 C -0.3785(4) 0.7269(3) 0.2499(4) 0.0279(13) Uani 1 1 d . . .
C39 C -0.3180(4) 0.7144(3) 0.4092(4) 0.0304(13) Uani 1 1 d . . .
H39 H -0.2974 0.6834 0.4565 0.037 Uiso 1 1 calc R . .
C40 C -0.2779(3) 0.8071(3) 0.5119(3) 0.0278(12) Uani 1 1 d . . .
H40 H -0.2613 0.7654 0.5513 0.033 Uiso 1 1 calc R . .
C41 C -0.3529(4) 0.8516(3) 0.5554(4) 0.0358(14) Uani 1 1 d . . .
H41A H -0.3729 0.8904 0.5138 0.043 Uiso 1 1 calc R . .
H41B H -0.4064 0.8210 0.5660 0.043 Uiso 1 1 calc R . .
C42 C -0.3167(4) 0.8835(3) 0.6453(4) 0.0372(15) Uani 1 1 d . . .
H42A H -0.3650 0.9130 0.6713 0.045 Uiso 1 1 calc R . .
H42B H -0.3014 0.8446 0.6885 0.045 Uiso 1 1 calc R . .
C43 C -0.2321(4) 0.9291(3) 0.6330(4) 0.0397(15) Uani 1 1 d . . .
H43A H -0.2483 0.9708 0.5947 0.048 Uiso 1 1 calc R . .
H43B H -0.2081 0.9466 0.6925 0.048 Uiso 1 1 calc R . .
C44 C -0.1597(4) 0.8848(3) 0.5886(4) 0.0343(14) Uani 1 1 d . . .
H44A H -0.1398 0.8459 0.6302 0.041 Uiso 1 1 calc R . .
H44B H -0.1059 0.9151 0.5784 0.041 Uiso 1 1 calc R . .
C45 C -0.1937(4) 0.8527(3) 0.4988(4) 0.0313(13) Uani 1 1 d . . .
H45 H -0.2090 0.8916 0.4545 0.038 Uiso 1 1 calc R . .
O4 O 0.9005(2) 1.01801(19) 0.4129(3) 0.0301(9) Uani 1 1 d . . .
H04 H 0.9534 1.0040 0.4282 0.045 Uiso 1 1 calc R . .
O5 O 0.6059(3) 1.05740(18) 0.6482(2) 0.0292(9) Uani 1 1 d . . .
H05 H 0.5836 1.0585 0.5949 0.044 Uiso 1 1 calc R . .
O6 O 0.9492(2) 0.99322(19) 0.7960(2) 0.0276(8) Uani 1 1 d . . .
H06 H 0.9139 0.9890 0.8389 0.041 Uiso 1 1 calc R . .
N7 N 0.6590(3) 1.1140(2) 0.3463(3) 0.0276(10) Uani 1 1 d . . .
N8 N 0.5443(3) 1.1144(2) 0.5001(3) 0.0300(11) Uani 1 1 d . . .
N9 N 0.6838(3) 1.0766(2) 0.9132(3) 0.0271(10) Uani 1 1 d . . .
N10 N 0.8688(3) 1.0300(2) 0.9436(3) 0.0233(10) Uani 1 1 d . . .
N11 N 1.1515(3) 1.0215(2) 0.6220(3) 0.0277(10) Uani 1 1 d . . .
N12 N 1.0764(3) 1.0246(2) 0.4383(3) 0.0268(10) Uani 1 1 d . . .
C46 C 1.0730(2) 1.08994(17) 0.4150(2) 0.0283(12) Uani 1 1 d . . .
H46 H 1.1281 1.1167 0.4159 0.034 Uiso 1 1 calc R . .
C47 C 0.9883(2) 1.12479(17) 0.3874(2) 0.0247(12) Uani 1 1 d R . .
C48 C 0.9884(2) 1.19607(17) 0.3602(2) 0.0278(12) Uani 1 1 d R . .
H48 H 1.0447 1.2213 0.3605 0.033 Uiso 1 1 calc R . .
C49 C 0.9086(4) 1.2306(3) 0.3328(3) 0.0275(12) Uani 1 1 d . . .
C50 C 0.9117(4) 1.3067(3) 0.3012(4) 0.0358(14) Uani 1 1 d . . .
H50A H 0.9308 1.3375 0.3520 0.054 Uiso 1 1 calc R . .
H50B H 0.8509 1.3211 0.2777 0.054 Uiso 1 1 calc R . .
H50C H 0.9554 1.3111 0.2533 0.054 Uiso 1 1 calc R . .
C51 C 0.8262(4) 1.1932(3) 0.3353(3) 0.0279(12) Uani 1 1 d . . .
H51 H 0.7708 1.2168 0.3180 0.034 Uiso 1 1 calc R . .
C52 C 0.8232(4) 1.1222(3) 0.3626(3) 0.0246(12) Uani 1 1 d . . .
C53 C 0.9037(4) 1.0876(3) 0.3875(4) 0.0268(12) Uani 1 1 d . . .
C54 C 0.7356(3) 1.0839(3) 0.3664(3) 0.0272(12) Uani 1 1 d . . .
H54 H 0.7360 1.0354 0.3843 0.033 Uiso 1 1 calc R . .
C55 C 0.5765(3) 1.0707(3) 0.3505(3) 0.0274(12) Uani 1 1 d . . .
H55 H 0.5920 1.0238 0.3792 0.033 Uiso 1 1 calc R . .
C56 C 0.5375(4) 1.0588(3) 0.2543(4) 0.0354(14) Uani 1 1 d . . .
H56A H 0.5281 1.1053 0.2239 0.042 Uiso 1 1 calc R . .
H56B H 0.5816 1.0311 0.2198 0.042 Uiso 1 1 calc R . .
C57 C 0.4469(4) 1.0190(3) 0.2544(4) 0.0421(16) Uani 1 1 d . . .
H57A H 0.4215 1.0147 0.1915 0.051 Uiso 1 1 calc R . .
H57B H 0.4576 0.9703 0.2782 0.051 Uiso 1 1 calc R . .
C58 C 0.3788(4) 1.0563(3) 0.3111(4) 0.0414(15) Uani 1 1 d . . .
H58A H 0.3223 1.0274 0.3127 0.050 Uiso 1 1 calc R . .
H58B H 0.3627 1.1029 0.2836 0.050 Uiso 1 1 calc R . .
C59 C 0.4177(4) 1.0674(3) 0.4064(4) 0.0350(14) Uani 1 1 d . . .
H59A H 0.4291 1.0206 0.4355 0.042 Uiso 1 1 calc R . .
H59B H 0.3728 1.0934 0.4420 0.042 Uiso 1 1 calc R . .
C60 C 0.5075(3) 1.1098(3) 0.4068(3) 0.0286(12) Uani 1 1 d . . .
H60 H 0.4960 1.1586 0.3818 0.034 Uiso 1 1 calc R . .
C61 C 0.5525(3) 1.1761(3) 0.5362(4) 0.0289(13) Uani 1 1 d . . .
H61 H 0.5371 1.2172 0.5013 0.035 Uiso 1 1 calc R . .
C62 C 0.5856(3) 1.1843(3) 0.6305(4) 0.0246(12) Uani 1 1 d . . .
C63 C 0.5877(3) 1.2512(3) 0.6697(4) 0.0274(12) Uani 1 1 d . . .
H63 H 0.5701 1.2913 0.6339 0.033 Uiso 1 1 calc R . .
C64 C 0.6150(3) 1.2612(3) 0.7605(4) 0.0274(12) Uani 1 1 d . . .
C65 C 0.6129(4) 1.3348(3) 0.8021(4) 0.0337(14) Uani 1 1 d . . .
H65A H 0.545(4) 1.352(3) 0.795(4) 0.040 Uiso 1 1 d . . .
H65B H 0.637(4) 1.334(3) 0.866(4) 0.040 Uiso 1 1 d . . .
H65C H 0.649(4) 1.365(3) 0.764(4) 0.040 Uiso 1 1 d . . .
C66 C 0.6405(4) 1.2010(3) 0.8104(4) 0.0292(13) Uani 1 1 d . . .
H66 H 0.6609 1.2068 0.8718 0.035 Uiso 1 1 calc R . .
C67 C 0.6373(3) 1.1330(3) 0.7739(4) 0.0246(12) Uani 1 1 d . . .
C68 C 0.6095(3) 1.1245(3) 0.6824(4) 0.0258(12) Uani 1 1 d . . .
C69 C 0.6632(3) 1.0709(3) 0.8290(4) 0.0281(12) Uani 1 1 d . . .
H69 H 0.6647 1.0254 0.8014 0.034 Uiso 1 1 calc R . .
C70 C 0.7077(4) 1.0109(3) 0.9632(3) 0.0264(12) Uani 1 1 d . . .
H70 H 0.7116 0.9704 0.9197 0.032 Uiso 1 1 calc R . .
C71 C 0.6332(4) 0.9959(3) 1.0295(4) 0.0360(14) Uani 1 1 d . . .
H71A H 0.6235 1.0389 1.0666 0.043 Uiso 1 1 calc R . .
H71B H 0.5752 0.9853 0.9953 0.043 Uiso 1 1 calc R . .
C72 C 0.6580(4) 0.9334(3) 1.0916(4) 0.0364(14) Uani 1 1 d . . .
H72A H 0.6102 0.9274 1.1362 0.044 Uiso 1 1 calc R . .
H72B H 0.6606 0.8892 1.0554 0.044 Uiso 1 1 calc R . .
C73 C 0.7490(4) 0.9455(3) 1.1408(4) 0.0327(13) Uani 1 1 d . . .
H73A H 0.7648 0.9036 1.1790 0.039 Uiso 1 1 calc R . .
H73B H 0.7452 0.9875 1.1808 0.039 Uiso 1 1 calc R . .
C74 C 0.8234(4) 0.9574(3) 1.0733(4) 0.0293(13) Uani 1 1 d . . .
H74A H 0.8297 0.9144 1.0356 0.035 Uiso 1 1 calc R . .
H74B H 0.8826 0.9660 1.1064 0.035 Uiso 1 1 calc R . .
C75 C 0.7995(3) 1.0214(3) 1.0125(3) 0.0243(11) Uani 1 1 d . . .
H75 H 0.7977 1.0654 1.0503 0.029 Uiso 1 1 calc R . .
C76 C 0.9125(3) 1.0891(3) 0.9415(3) 0.0256(12) Uani 1 1 d . . .
H76 H 0.8996 1.1249 0.9844 0.031 Uiso 1 1 calc R . .
C77 C 0.9818(4) 1.1033(3) 0.8753(3) 0.0230(11) Uani 1 1 d . . .
C78 C 1.0342(4) 1.1650(3) 0.8834(4) 0.0284(12) Uani 1 1 d . . .
H78 H 1.0234 1.1973 0.9312 0.034 Uiso 1 1 calc R . .
C79 C 1.1016(4) 1.1806(3) 0.8239(3) 0.0265(12) Uani 1 1 d . . .
C80 C 1.1596(4) 1.2471(3) 0.8368(4) 0.0325(13) Uani 1 1 d . . .
H80A H 1.2125 1.2367 0.8776 0.049 Uiso 1 1 calc R . .
H80B H 1.1230 1.2849 0.8629 0.049 Uiso 1 1 calc R . .
H80C H 1.1808 1.2628 0.7781 0.049 Uiso 1 1 calc R . .
C81 C 1.1164(3) 1.1323(3) 0.7556(3) 0.0252(12) Uani 1 1 d . . .
H81 H 1.1630 1.1422 0.7149 0.030 Uiso 1 1 calc R . .
C82 C 1.0664(3) 1.0699(3) 0.7436(3) 0.0225(11) Uani 1 1 d . . .
C83 C 0.9984(3) 1.0551(3) 0.8064(3) 0.0220(11) Uani 1 1 d . . .
C84 C 1.0844(3) 1.0175(3) 0.6732(3) 0.0237(11) Uani 1 1 d . . .
H84 H 1.0436 0.9784 0.6655 0.028 Uiso 1 1 calc R . .
C85 C 1.1624(3) 0.9629(3) 0.5578(3) 0.0237(11) Uani 1 1 d . . .
H85 H 1.1094 0.9296 0.5616 0.028 Uiso 1 1 calc R . .
C86 C 1.2505(4) 0.9223(3) 0.5815(4) 0.0314(13) Uani 1 1 d . . .
H86A H 1.2485 0.9039 0.6440 0.038 Uiso 1 1 calc R . .
H86B H 1.3031 0.9553 0.5790 0.038 Uiso 1 1 calc R . .
C87 C 1.2639(4) 0.8604(3) 0.5166(4) 0.0353(14) Uani 1 1 d . . .
H87A H 1.3229 0.8366 0.5320 0.042 Uiso 1 1 calc R . .
H87B H 1.2144 0.8251 0.5230 0.042 Uiso 1 1 calc R . .
C88 C 1.2632(4) 0.8866(3) 0.4200(4) 0.0321(13) Uani 1 1 d . . .
H88A H 1.2660 0.8454 0.3785 0.038 Uiso 1 1 calc R . .
H88B H 1.3178 0.9165 0.4115 0.038 Uiso 1 1 calc R . .
C89 C 1.1778(4) 0.9296(3) 0.3967(4) 0.0309(13) Uani 1 1 d . . .
H89A H 1.1239 0.8979 0.3979 0.037 Uiso 1 1 calc R . .
H89B H 1.1813 0.9486 0.3346 0.037 Uiso 1 1 calc R . .
C90 C 1.1655(3) 0.9911(3) 0.4619(3) 0.0239(11) Uani 1 1 d . . .
H90 H 1.2160 1.0265 0.4572 0.029 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 H01 109.5 . . ?
C23 O2 H2 109.5 . . ?
C38 O3 H03 109.5 . . ?
C9 N1 C10 118.9(5) . . ?
C16 N2 C15 116.5(4) . . ?
C24 N3 C25 117.4(5) . . ?
C31 N4 C30 116.1(5) . . ?
C39 N5 C40 117.4(5) . . ?
C1 N6 C45 115.6(5) . . ?
N6 C1 C2 121.8(5) . . ?
N6 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C8 117.8(5) . . ?
C3 C2 C1 121.8(5) . . ?
C8 C2 C1 120.4(5) . . ?
C2 C3 C4 121.9(5) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C6 C4 C3 117.6(5) . . ?
C6 C4 C5 120.4(5) . . ?
C3 C4 C5 122.0(5) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 121.8(5) . . ?
C4 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 119.7(5) . . ?
C8 C7 C9 122.2(5) . . ?
C6 C7 C9 118.1(5) . . ?
O1 C8 C7 121.8(5) . . ?
O1 C8 C2 117.0(5) . . ?
C7 C8 C2 121.2(5) . . ?
N1 C9 C7 121.9(5) . . ?
N1 C9 H9 119.1 . . ?
C7 C9 H9 119.1 . . ?
N1 C10 C15 110.1(4) . . ?
N1 C10 C11 109.1(4) . . ?
C15 C10 C11 111.1(4) . . ?
N1 C10 H10 108.8 . . ?
C15 C10 H10 108.8 . . ?
C11 C10 H10 108.8 . . ?
C10 C11 C12 111.6(4) . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 109.9(5) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 110.6(5) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 111.9(4) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 C10 109.4(4) . . ?
N2 C15 C14 110.0(4) . . ?
C10 C15 C14 108.9(4) . . ?
N2 C15 H15 109.5 . . ?
C10 C15 H15 109.5 . . ?
C14 C15 H15 109.5 . . ?
N2 C16 C17 121.7(5) . . ?
N2 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C23 118.5(5) . . ?
C18 C17 C16 122.2(5) . . ?
C23 C17 C16 119.4(5) . . ?
C19 C18 C17 122.4(5) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C21 C19 C18 118.2(5) . . ?
C21 C19 C20 120.6(5) . . ?
C18 C19 C20 121.1(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 C22 121.6(5) . . ?
C19 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C23 C22 C21 118.9(5) . . ?
C23 C22 C24 122.5(5) . . ?
C21 C22 C24 118.6(5) . . ?
O2 C23 C22 120.1(5) . . ?
O2 C23 C17 119.5(5) . . ?
C22 C23 C17 120.4(5) . . ?
N3 C24 C22 123.2(5) . . ?
N3 C24 H24 118.4 . . ?
C22 C24 H24 118.4 . . ?
N3 C25 C30 110.7(4) . . ?
N3 C25 C26 108.7(4) . . ?
C30 C25 C26 111.1(5) . . ?
N3 C25 H25 108.8 . . ?
C30 C25 H25 108.8 . . ?
C26 C25 H25 108.8 . . ?
C27 C26 C25 111.4(5) . . ?
C27 C26 H26A 109.3 . . ?
C25 C26 H26A 109.3 . . ?
C27 C26 H26B 109.3 . . ?
C25 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
C28 C27 C26 110.9(5) . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.0 . . ?
C29 C28 C27 110.9(5) . . ?
C29 C28 H28A 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 108.1 . . ?
C28 C29 C30 113.0(5) . . ?
C28 C29 H29A 109.0 . . ?
C30 C29 H29A 109.0 . . ?
C28 C29 H29B 109.0 . . ?
C30 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
N4 C30 C25 108.5(4) . . ?
N4 C30 C29 109.3(4) . . ?
C25 C30 C29 108.2(5) . . ?
N4 C30 H30 110.3 . . ?
C25 C30 H30 110.3 . . ?
C29 C30 H30 110.3 . . ?
N4 C31 C32 121.3(5) . . ?
N4 C31 H31 119.3 . . ?
C32 C31 H31 119.3 . . ?
C33 C32 C38 118.8(5) . . ?
C33 C32 C31 121.4(5) . . ?
C38 C32 C31 119.7(5) . . ?
C32 C33 C34 122.5(5) . . ?
C32 C33 H33 118.8 . . ?
C34 C33 H33 118.8 . . ?
C36 C34 C33 117.8(5) . . ?
C36 C34 C35 121.9(5) . . ?
C33 C34 C35 120.2(5) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 C37 121.8(5) . . ?
C34 C36 H36 119.1 . . ?
C37 C36 H36 119.1 . . ?
C38 C37 C36 119.2(5) . . ?
C38 C37 C39 121.1(5) . . ?
C36 C37 C39 119.7(5) . . ?
O3 C38 C37 121.4(5) . . ?
O3 C38 C32 118.7(5) . . ?
C37 C38 C32 119.9(5) . . ?
N5 C39 C37 122.0(5) . . ?
N5 C39 H39 119.0 . . ?
C37 C39 H39 119.0 . . ?
N5 C40 C45 109.2(4) . . ?
N5 C40 C41 108.1(4) . . ?
C45 C40 C41 110.1(4) . . ?
N5 C40 H40 109.8 . . ?
C45 C40 H40 109.8 . . ?
C41 C40 H40 109.8 . . ?
C42 C41 C40 110.5(5) . . ?
C42 C41 H41A 109.6 . . ?
C40 C41 H41A 109.6 . . ?
C42 C41 H41B 109.6 . . ?
C40 C41 H41B 109.6 . . ?
H41A C41 H41B 108.1 . . ?
C43 C42 C41 111.5(5) . . ?
C43 C42 H42A 109.3 . . ?
C41 C42 H42A 109.3 . . ?
C43 C42 H42B 109.3 . . ?
C41 C42 H42B 109.3 . . ?
H42A C42 H42B 108.0 . . ?
C44 C43 C42 109.3(5) . . ?
C44 C43 H43A 109.8 . . ?
C42 C43 H43A 109.8 . . ?
C44 C43 H43B 109.8 . . ?
C42 C43 H43B 109.8 . . ?
H43A C43 H43B 108.3 . . ?
C43 C44 C45 112.7(5) . . ?
C43 C44 H44A 109.0 . . ?
C45 C44 H44A 109.0 . . ?
C43 C44 H44B 109.0 . . ?
C45 C44 H44B 109.0 . . ?
H44A C44 H44B 107.8 . . ?
N6 C45 C40 107.9(4) . . ?
N6 C45 C44 109.5(5) . . ?
C40 C45 C44 110.3(4) . . ?
N6 C45 H45 109.7 . . ?
C40 C45 H45 109.7 . . ?
C44 C45 H45 109.7 . . ?
C53 O4 H04 109.5 . . ?
C68 O5 H05 109.5 . . ?
C83 O6 H06 109.5 . . ?
C54 N7 C55 117.6(5) . . ?
C61 N8 C60 118.1(5) . . ?
C69 N9 C70 117.5(5) . . ?
C76 N10 C75 118.0(4) . . ?
C84 N11 C85 116.9(4) . . ?
C46 N12 C90 119.9(4) . . ?
N12 C46 C47 122.4(2) . . ?
N12 C46 H46 118.8 . . ?
C47 C46 H46 118.8 . . ?
C48 C47 C53 118.9(3) . . ?
C48 C47 C46 120.2 . . ?
C53 C47 C46 120.9(3) . . ?
C49 C48 C47 121.4(3) . . ?
C49 C48 H48 119.3 . . ?
C47 C48 H48 119.3 . . ?
C48 C49 C51 118.4(5) . . ?
C48 C49 C50 120.0(5) . . ?
C51 C49 C50 121.5(5) . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C52 C51 C49 121.8(5) . . ?
C52 C51 H51 119.1 . . ?
C49 C51 H51 119.1 . . ?
C53 C52 C51 119.2(5) . . ?
C53 C52 C54 119.7(5) . . ?
C51 C52 C54 121.1(5) . . ?
O4 C53 C52 119.0(5) . . ?
O4 C53 C47 120.8(5) . . ?
C52 C53 C47 120.1(5) . . ?
N7 C54 C52 122.2(5) . . ?
N7 C54 H54 118.9 . . ?
C52 C54 H54 118.9 . . ?
N7 C55 C60 108.9(4) . . ?
N7 C55 C56 108.6(4) . . ?
C60 C55 C56 110.5(5) . . ?
N7 C55 H55 109.6 . . ?
C60 C55 H55 109.6 . . ?
C56 C55 H55 109.6 . . ?
C57 C56 C55 111.2(4) . . ?
C57 C56 H56A 109.4 . . ?
C55 C56 H56A 109.4 . . ?
C57 C56 H56B 109.4 . . ?
C55 C56 H56B 109.4 . . ?
H56A C56 H56B 108.0 . . ?
C58 C57 C56 111.8(5) . . ?
C58 C57 H57A 109.3 . . ?
C56 C57 H57A 109.3 . . ?
C58 C57 H57B 109.3 . . ?
C56 C57 H57B 109.3 . . ?
H57A C57 H57B 107.9 . . ?
C57 C58 C59 110.6(5) . . ?
C57 C58 H58A 109.5 . . ?
C59 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
C59 C58 H58B 109.5 . . ?
H58A C58 H58B 108.1 . . ?
C58 C59 C60 111.2(5) . . ?
C58 C59 H59A 109.4 . . ?
C60 C59 H59A 109.4 . . ?
C58 C59 H59B 109.4 . . ?
C60 C59 H59B 109.4 . . ?
H59A C59 H59B 108.0 . . ?
N8 C60 C55 108.6(4) . . ?
N8 C60 C59 108.2(4) . . ?
C55 C60 C59 109.6(4) . . ?
N8 C60 H60 110.1 . . ?
C55 C60 H60 110.1 . . ?
C59 C60 H60 110.1 . . ?
N8 C61 C62 120.9(5) . . ?
N8 C61 H61 119.6 . . ?
C62 C61 H61 119.6 . . ?
C63 C62 C68 120.0(5) . . ?
C63 C62 C61 119.6(5) . . ?
C68 C62 C61 120.2(5) . . ?
C62 C63 C64 121.7(5) . . ?
C62 C63 H63 119.1 . . ?
C64 C63 H63 119.2 . . ?
C66 C64 C63 117.3(5) . . ?
C66 C64 C65 122.4(5) . . ?
C63 C64 C65 120.3(5) . . ?
C64 C65 H65A 106(3) . . ?
C64 C65 H65B 112(3) . . ?
H65A C65 H65B 114(4) . . ?
C64 C65 H65C 106(3) . . ?
H65A C65 H65C 108(5) . . ?
H65B C65 H65C 112(5) . . ?
C67 C66 C64 122.6(5) . . ?
C67 C66 H66 118.7 . . ?
C64 C66 H66 118.7 . . ?
C66 C67 C68 118.8(5) . . ?
C66 C67 C69 120.9(5) . . ?
C68 C67 C69 120.3(5) . . ?
O5 C68 C62 122.5(5) . . ?
O5 C68 C67 117.9(5) . . ?
C62 C68 C67 119.6(5) . . ?
N9 C69 C67 121.6(5) . . ?
N9 C69 H69 119.2 . . ?
C67 C69 H69 119.2 . . ?
N9 C70 C75 108.7(4) . . ?
N9 C70 C71 108.5(4) . . ?
C75 C70 C71 111.0(4) . . ?
N9 C70 H70 109.6 . . ?
C75 C70 H70 109.6 . . ?
C71 C70 H70 109.6 . . ?
C72 C71 C70 111.8(5) . . ?
C72 C71 H71A 109.2 . . ?
C70 C71 H71A 109.2 . . ?
C72 C71 H71B 109.2 . . ?
C70 C71 H71B 109.2 . . ?
H71A C71 H71B 107.9 . . ?
C73 C72 C71 111.0(5) . . ?
C73 C72 H72A 109.4 . . ?
C71 C72 H72A 109.4 . . ?
C73 C72 H72B 109.4 . . ?
C71 C72 H72B 109.4 . . ?
H72A C72 H72B 108.0 . . ?
C72 C73 C74 110.3(5) . . ?
C72 C73 H73A 109.6 . . ?
C74 C73 H73A 109.6 . . ?
C72 C73 H73B 109.6 . . ?
C74 C73 H73B 109.6 . . ?
H73A C73 H73B 108.1 . . ?
C73 C74 C75 110.4(4) . . ?
C73 C74 H74A 109.6 . . ?
C75 C74 H74A 109.6 . . ?
C73 C74 H74B 109.6 . . ?
C75 C74 H74B 109.6 . . ?
H74A C74 H74B 108.1 . . ?
N10 C75 C70 107.6(4) . . ?
N10 C75 C74 110.2(4) . . ?
C70 C75 C74 110.9(4) . . ?
N10 C75 H75 109.4 . . ?
C70 C75 H75 109.4 . . ?
C74 C75 H75 109.4 . . ?
N10 C76 C77 122.3(5) . . ?
N10 C76 H76 118.9 . . ?
C77 C76 H76 118.8 . . ?
C83 C77 C78 119.3(5) . . ?
C83 C77 C76 121.4(5) . . ?
C78 C77 C76 119.3(5) . . ?
C79 C78 C77 121.9(5) . . ?
C79 C78 H78 119.1 . . ?
C77 C78 H78 119.1 . . ?
C81 C79 C78 117.8(5) . . ?
C81 C79 C80 121.8(5) . . ?
C78 C79 C80 120.4(5) . . ?
C79 C80 H80A 109.5 . . ?
C79 C80 H80B 109.5 . . ?
H80A C80 H80B 109.5 . . ?
C79 C80 H80C 109.5 . . ?
H80A C80 H80C 109.5 . . ?
H80B C80 H80C 109.5 . . ?
C79 C81 C82 123.3(5) . . ?
C79 C81 H81 118.4 . . ?
C82 C81 H81 118.4 . . ?
C81 C82 C83 117.5(5) . . ?
C81 C82 C84 123.2(4) . . ?
C83 C82 C84 119.2(4) . . ?
O6 C83 C77 121.5(4) . . ?
O6 C83 C82 118.2(4) . . ?
C77 C83 C82 120.2(5) . . ?
N11 C84 C82 123.6(5) . . ?
N11 C84 H84 118.2 . . ?
C82 C84 H84 118.2 . . ?
N11 C85 C90 110.6(4) . . ?
N11 C85 C86 110.0(4) . . ?
C90 C85 C86 109.2(4) . . ?
N11 C85 H85 109.0 . . ?
C90 C85 H85 109.0 . . ?
C86 C85 H85 109.0 . . ?
C85 C86 C87 111.5(5) . . ?
C85 C86 H86A 109.3 . . ?
C87 C86 H86A 109.3 . . ?
C85 C86 H86B 109.3 . . ?
C87 C86 H86B 109.3 . . ?
H86A C86 H86B 108.0 . . ?
C88 C87 C86 110.5(5) . . ?
C88 C87 H87A 109.5 . . ?
C86 C87 H87A 109.5 . . ?
C88 C87 H87B 109.5 . . ?
C86 C87 H87B 109.5 . . ?
H87A C87 H87B 108.1 . . ?
C87 C88 C89 111.1(4) . . ?
C87 C88 H88A 109.4 . . ?
C89 C88 H88A 109.4 . . ?
C87 C88 H88B 109.4 . . ?
C89 C88 H88B 109.4 . . ?
H88A C88 H88B 108.0 . . ?
C88 C89 C90 112.4(4) . . ?
C88 C89 H89A 109.1 . . ?
C90 C89 H89A 109.1 . . ?
C88 C89 H89B 109.1 . . ?
C90 C89 H89B 109.1 . . ?
H89A C89 H89B 107.9 . . ?
N12 C90 C85 107.9(4) . . ?
N12 C90 C89 107.6(4) . . ?
C85 C90 C89 109.7(4) . . ?
N12 C90 H90 110.5 . . ?
C85 C90 H90 110.5 . . ?
C89 C90 H90 110.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.366(6) . ?
O1 H01 0.8400 . ?
O2 C23 1.357(6) . ?
O2 H2 0.8400 . ?
O3 C38 1.363(6) . ?
O3 H03 0.8400 . ?
N1 C9 1.275(6) . ?
N1 C10 1.468(6) . ?
N2 C16 1.297(6) . ?
N2 C15 1.458(6) . ?
N3 C24 1.299(7) . ?
N3 C25 1.472(7) . ?
N4 C31 1.291(7) . ?
N4 C30 1.468(6) . ?
N5 C39 1.282(7) . ?
N5 C40 1.486(7) . ?
N6 C1 1.292(6) . ?
N6 C45 1.465(6) . ?
C1 C2 1.466(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.400(7) . ?
C2 C8 1.410(7) . ?
C3 C4 1.406(7) . ?
C3 H3 0.9500 . ?
C4 C6 1.389(7) . ?
C4 C5 1.497(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.392(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.371(7) . ?
C7 C9 1.462(7) . ?
C9 H9 0.9500 . ?
C10 C15 1.513(7) . ?
C10 C11 1.518(7) . ?
C10 H10 1.0000 . ?
C11 C12 1.528(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.491(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.516(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.519(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15 1.0000 . ?
C16 C17 1.465(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(7) . ?
C17 C23 1.394(7) . ?
C18 C19 1.380(7) . ?
C18 H18 0.9500 . ?
C19 C21 1.379(7) . ?
C19 C20 1.524(7) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.399(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(7) . ?
C22 C24 1.441(7) . ?
C24 H24 0.9500 . ?
C25 C30 1.523(7) . ?
C25 C26 1.526(7) . ?
C25 H25 1.0000 . ?
C26 C27 1.524(7) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.512(8) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.511(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.542(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30 1.0000 . ?
C31 C32 1.469(7) . ?
C31 H31 0.9500 . ?
C32 C33 1.391(7) . ?
C32 C38 1.403(7) . ?
C33 C34 1.391(7) . ?
C33 H33 0.9500 . ?
C34 C36 1.378(7) . ?
C34 C35 1.519(7) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 C37 1.407(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.395(7) . ?
C37 C39 1.467(7) . ?
C39 H39 0.9500 . ?
C40 C45 1.520(7) . ?
C40 C41 1.545(7) . ?
C40 H40 1.0000 . ?
C41 C42 1.532(8) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.524(7) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.521(7) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.524(7) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 H45 1.0000 . ?
O4 C53 1.361(6) . ?
O4 H04 0.8400 . ?
O5 C68 1.359(6) . ?
O5 H05 0.8400 . ?
O6 C83 1.374(6) . ?
O6 H06 0.8400 . ?
N7 C54 1.279(6) . ?
N7 C55 1.460(6) . ?
N8 C61 1.280(7) . ?
N8 C60 1.463(6) . ?
N9 C69 1.274(6) . ?
N9 C70 1.472(6) . ?
N10 C76 1.283(6) . ?
N10 C75 1.480(6) . ?
N11 C84 1.270(6) . ?
N11 C85 1.467(6) . ?
N12 C46 1.275(5) . ?
N12 C90 1.476(6) . ?
C46 C47 1.4460 . ?
C46 H46 0.9500 . ?
C47 C48 1.3986 . ?
C47 C53 1.423(6) . ?
C48 C49 1.382(6) . ?
C48 H48 0.9500 . ?
C49 C51 1.398(7) . ?
C49 C50 1.506(7) . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 C52 1.397(7) . ?
C51 H51 0.9500 . ?
C52 C53 1.383(7) . ?
C52 C54 1.473(7) . ?
C54 H54 0.9500 . ?
C55 C60 1.527(7) . ?
C55 C56 1.527(7) . ?
C55 H55 1.0000 . ?
C56 C57 1.523(7) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C57 C58 1.506(8) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C58 C59 1.512(7) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 C60 1.538(7) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C60 H60 1.0000 . ?
C61 C62 1.466(7) . ?
C61 H61 0.9500 . ?
C62 C63 1.384(7) . ?
C62 C68 1.396(7) . ?
C63 C64 1.398(7) . ?
C63 H63 0.9500 . ?
C64 C66 1.393(7) . ?
C64 C65 1.515(7) . ?
C65 H65A 1.05(6) . ?
C65 H65B 1.00(6) . ?
C65 H65C 0.97(6) . ?
C66 C67 1.388(7) . ?
C66 H66 0.9500 . ?
C67 C68 1.407(7) . ?
C67 C69 1.463(7) . ?
C69 H69 0.9500 . ?
C70 C75 1.515(7) . ?
C70 C71 1.527(7) . ?
C70 H70 1.0000 . ?
C71 C72 1.525(8) . ?
C71 H71A 0.9900 . ?
C71 H71B 0.9900 . ?
C72 C73 1.508(8) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C73 C74 1.528(7) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C74 C75 1.532(7) . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C75 H75 1.0000 . ?
C76 C77 1.466(7) . ?
C76 H76 0.9500 . ?
C77 C83 1.393(6) . ?
C77 C78 1.394(7) . ?
C78 C79 1.383(7) . ?
C78 H78 0.9500 . ?
C79 C81 1.383(7) . ?
C79 C80 1.520(7) . ?
C80 H80A 0.9800 . ?
C80 H80B 0.9800 . ?
C80 H80C 0.9800 . ?
C81 C82 1.388(7) . ?
C81 H81 0.9500 . ?
C82 C83 1.420(6) . ?
C82 C84 1.466(6) . ?
C84 H84 0.9500 . ?
C85 C90 1.518(7) . ?
C85 C86 1.526(7) . ?
C85 H85 1.0000 . ?
C86 C87 1.528(7) . ?
C86 H86A 0.9900 . ?
C86 H86B 0.9900 . ?
C87 C88 1.513(7) . ?
C87 H87A 0.9900 . ?
C87 H87B 0.9900 . ?
C88 C89 1.515(7) . ?
C88 H88A 0.9900 . ?
C88 H88B 0.9900 . ?
C89 C90 1.522(7) . ?
C89 H89A 0.9900 . ?
C89 H89B 0.9900 . ?
C90 H90 1.0000 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H01 N1 0.84 1.88 2.618(5) 145.1 .
O2 H2 N3 0.84 1.87 2.619(6) 148.6 .
O3 H03 N5 0.84 1.87 2.599(6) 144.3 .
O4 H04 N12 0.84 1.84 2.590(6) 147.4 .
O5 H05 N8 0.84 1.83 2.567(6) 146.3 .
O6 H06 N10 0.84 1.88 2.620(5) 146.8 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C45 N6 C1 C2 176.9(5) . . . . ?
N6 C1 C2 C3 1.3(8) . . . . ?
N6 C1 C2 C8 -179.5(5) . . . . ?
C8 C2 C3 C4 0.8(8) . . . . ?
C1 C2 C3 C4 179.9(5) . . . . ?
C2 C3 C4 C6 -0.6(8) . . . . ?
C2 C3 C4 C5 180.0(5) . . . . ?
C3 C4 C6 C7 0.4(8) . . . . ?
C5 C4 C6 C7 179.9(5) . . . . ?
C4 C6 C7 C8 -0.5(8) . . . . ?
C4 C6 C7 C9 179.1(5) . . . . ?
C6 C7 C8 O1 179.8(5) . . . . ?
C9 C7 C8 O1 0.2(8) . . . . ?
C6 C7 C8 C2 0.8(8) . . . . ?
C9 C7 C8 C2 -178.8(5) . . . . ?
C3 C2 C8 O1 -179.9(5) . . . . ?
C1 C2 C8 O1 0.9(8) . . . . ?
C3 C2 C8 C7 -0.9(8) . . . . ?
C1 C2 C8 C7 180.0(5) . . . . ?
C10 N1 C9 C7 176.2(5) . . . . ?
C8 C7 C9 N1 3.8(8) . . . . ?
C6 C7 C9 N1 -175.7(5) . . . . ?
C9 N1 C10 C15 119.3(5) . . . . ?
C9 N1 C10 C11 -118.5(5) . . . . ?
N1 C10 C11 C12 -178.3(4) . . . . ?
C15 C10 C11 C12 -56.7(6) . . . . ?
C10 C11 C12 C13 56.4(6) . . . . ?
C11 C12 C13 C14 -56.6(6) . . . . ?
C12 C13 C14 C15 58.7(6) . . . . ?
C16 N2 C15 C10 128.5(5) . . . . ?
C16 N2 C15 C14 -112.0(5) . . . . ?
N1 C10 C15 N2 -62.7(5) . . . . ?
C11 C10 C15 N2 176.3(4) . . . . ?
N1 C10 C15 C14 177.1(4) . . . . ?
C11 C10 C15 C14 56.0(6) . . . . ?
C13 C14 C15 N2 -177.3(4) . . . . ?
C13 C14 C15 C10 -57.4(6) . . . . ?
C15 N2 C16 C17 179.3(5) . . . . ?
N2 C16 C17 C18 -1.7(8) . . . . ?
N2 C16 C17 C23 177.4(5) . . . . ?
C23 C17 C18 C19 -0.1(8) . . . . ?
C16 C17 C18 C19 179.0(5) . . . . ?
C17 C18 C19 C21 -1.7(8) . . . . ?
C17 C18 C19 C20 -177.8(5) . . . . ?
C18 C19 C21 C22 1.8(8) . . . . ?
C20 C19 C21 C22 177.9(5) . . . . ?
C19 C21 C22 C23 -0.1(8) . . . . ?
C19 C21 C22 C24 -179.9(5) . . . . ?
C21 C22 C23 O2 178.1(5) . . . . ?
C24 C22 C23 O2 -2.0(8) . . . . ?
C21 C22 C23 C17 -1.9(8) . . . . ?
C24 C22 C23 C17 178.0(5) . . . . ?
C18 C17 C23 O2 -178.1(5) . . . . ?
C16 C17 C23 O2 2.8(8) . . . . ?
C18 C17 C23 C22 2.0(8) . . . . ?
C16 C17 C23 C22 -177.2(5) . . . . ?
C25 N3 C24 C22 178.0(5) . . . . ?
C23 C22 C24 N3 4.0(9) . . . . ?
C21 C22 C24 N3 -176.2(5) . . . . ?
C24 N3 C25 C30 118.0(5) . . . . ?
C24 N3 C25 C26 -119.8(5) . . . . ?
N3 C25 C26 C27 180.0(5) . . . . ?
C30 C25 C26 C27 -58.0(6) . . . . ?
C25 C26 C27 C28 55.7(7) . . . . ?
C26 C27 C28 C29 -54.3(7) . . . . ?
C27 C28 C29 C30 56.2(7) . . . . ?
C31 N4 C30 C25 130.3(5) . . . . ?
C31 N4 C30 C29 -111.9(5) . . . . ?
N3 C25 C30 N4 -63.8(6) . . . . ?
C26 C25 C30 N4 175.3(4) . . . . ?
N3 C25 C30 C29 177.7(4) . . . . ?
C26 C25 C30 C29 56.8(6) . . . . ?
C28 C29 C30 N4 -174.8(5) . . . . ?
C28 C29 C30 C25 -56.8(6) . . . . ?
C30 N4 C31 C32 175.2(4) . . . . ?
N4 C31 C32 C33 -5.0(8) . . . . ?
N4 C31 C32 C38 178.4(5) . . . . ?
C38 C32 C33 C34 -1.0(8) . . . . ?
C31 C32 C33 C34 -177.6(5) . . . . ?
C32 C33 C34 C36 -0.7(8) . . . . ?
C32 C33 C34 C35 176.4(5) . . . . ?
C33 C34 C36 C37 1.0(8) . . . . ?
C35 C34 C36 C37 -176.0(5) . . . . ?
C34 C36 C37 C38 0.4(8) . . . . ?
C34 C36 C37 C39 179.2(5) . . . . ?
C36 C37 C38 O3 177.3(5) . . . . ?
C39 C37 C38 O3 -1.5(8) . . . . ?
C36 C37 C38 C32 -2.1(8) . . . . ?
C39 C37 C38 C32 179.1(5) . . . . ?
C33 C32 C38 O3 -177.0(5) . . . . ?
C31 C32 C38 O3 -0.4(7) . . . . ?
C33 C32 C38 C37 2.4(8) . . . . ?
C31 C32 C38 C37 179.1(5) . . . . ?
C40 N5 C39 C37 179.9(4) . . . . ?
C38 C37 C39 N5 4.2(8) . . . . ?
C36 C37 C39 N5 -174.6(5) . . . . ?
C39 N5 C40 C45 119.6(5) . . . . ?
C39 N5 C40 C41 -120.6(5) . . . . ?
N5 C40 C41 C42 -176.1(4) . . . . ?
C45 C40 C41 C42 -56.9(6) . . . . ?
C40 C41 C42 C43 57.3(6) . . . . ?
C41 C42 C43 C44 -56.1(7) . . . . ?
C42 C43 C44 C45 56.4(7) . . . . ?
C1 N6 C45 C40 129.6(5) . . . . ?
C1 N6 C45 C44 -110.3(6) . . . . ?
N5 C40 C45 N6 -65.4(6) . . . . ?
C41 C40 C45 N6 176.0(4) . . . . ?
N5 C40 C45 C44 175.0(4) . . . . ?
C41 C40 C45 C44 56.4(6) . . . . ?
C43 C44 C45 N6 -176.0(5) . . . . ?
C43 C44 C45 C40 -57.4(6) . . . . ?
C90 N12 C46 C47 177.2(3) . . . . ?
N12 C46 C47 C48 -178.3(3) . . . . ?
N12 C46 C47 C53 1.8(3) . . . . ?
C53 C47 C48 C49 -0.6(3) . . . . ?
C46 C47 C48 C49 179.5(3) . . . . ?
C47 C48 C49 C51 1.9(5) . . . . ?
C47 C48 C49 C50 -178.1(3) . . . . ?
C48 C49 C51 C52 -1.5(7) . . . . ?
C50 C49 C51 C52 178.5(5) . . . . ?
C49 C51 C52 C53 -0.3(8) . . . . ?
C49 C51 C52 C54 178.9(5) . . . . ?
C51 C52 C53 O4 -179.2(4) . . . . ?
C54 C52 C53 O4 1.6(7) . . . . ?
C51 C52 C53 C47 1.6(7) . . . . ?
C54 C52 C53 C47 -177.6(4) . . . . ?
C48 C47 C53 O4 179.6(3) . . . . ?
C46 C47 C53 O4 -0.5(6) . . . . ?
C48 C47 C53 C52 -1.2(6) . . . . ?
C46 C47 C53 C52 178.7(3) . . . . ?
C55 N7 C54 C52 178.7(4) . . . . ?
C53 C52 C54 N7 178.2(5) . . . . ?
C51 C52 C54 N7 -1.0(8) . . . . ?
C54 N7 C55 C60 129.3(5) . . . . ?
C54 N7 C55 C56 -110.4(5) . . . . ?
N7 C55 C56 C57 -175.4(5) . . . . ?
C60 C55 C56 C57 -56.0(6) . . . . ?
C55 C56 C57 C58 55.4(7) . . . . ?
C56 C57 C58 C59 -55.7(7) . . . . ?
C57 C58 C59 C60 57.2(7) . . . . ?
C61 N8 C60 C55 123.5(5) . . . . ?
C61 N8 C60 C59 -117.6(5) . . . . ?
N7 C55 C60 N8 -65.8(5) . . . . ?
C56 C55 C60 N8 175.0(4) . . . . ?
N7 C55 C60 C59 176.1(4) . . . . ?
C56 C55 C60 C59 56.9(6) . . . . ?
C58 C59 C60 N8 -176.3(5) . . . . ?
C58 C59 C60 C55 -58.0(6) . . . . ?
C60 N8 C61 C62 177.6(4) . . . . ?
N8 C61 C62 C63 -175.5(5) . . . . ?
N8 C61 C62 C68 0.7(8) . . . . ?
C68 C62 C63 C64 1.2(8) . . . . ?
C61 C62 C63 C64 177.3(4) . . . . ?
C62 C63 C64 C66 0.2(7) . . . . ?
C62 C63 C64 C65 -177.6(5) . . . . ?
C63 C64 C66 C67 -1.7(8) . . . . ?
C65 C64 C66 C67 176.0(5) . . . . ?
C64 C66 C67 C68 1.7(8) . . . . ?
C64 C66 C67 C69 -179.0(5) . . . . ?
C63 C62 C68 O5 177.9(5) . . . . ?
C61 C62 C68 O5 1.8(7) . . . . ?
C63 C62 C68 C67 -1.2(7) . . . . ?
C61 C62 C68 C67 -177.3(4) . . . . ?
C66 C67 C68 O5 -179.3(4) . . . . ?
C69 C67 C68 O5 1.4(7) . . . . ?
C66 C67 C68 C62 -0.3(7) . . . . ?
C69 C67 C68 C62 -179.6(5) . . . . ?
C70 N9 C69 C67 179.1(4) . . . . ?
C66 C67 C69 N9 4.6(7) . . . . ?
C68 C67 C69 N9 -176.1(5) . . . . ?
C69 N9 C70 C75 126.7(5) . . . . ?
C69 N9 C70 C71 -112.6(5) . . . . ?
N9 C70 C71 C72 -173.5(4) . . . . ?
C75 C70 C71 C72 -54.2(6) . . . . ?
C70 C71 C72 C73 55.4(6) . . . . ?
C71 C72 C73 C74 -57.2(6) . . . . ?
C72 C73 C74 C75 58.4(6) . . . . ?
C76 N10 C75 C70 117.8(5) . . . . ?
C76 N10 C75 C74 -121.2(5) . . . . ?
N9 C70 C75 N10 -65.2(5) . . . . ?
C71 C70 C75 N10 175.6(4) . . . . ?
N9 C70 C75 C74 174.3(4) . . . . ?
C71 C70 C75 C74 55.1(6) . . . . ?
C73 C74 C75 N10 -176.5(4) . . . . ?
C73 C74 C75 C70 -57.4(6) . . . . ?
C75 N10 C76 C77 -179.3(4) . . . . ?
N10 C76 C77 C83 5.2(8) . . . . ?
N10 C76 C77 C78 -172.5(5) . . . . ?
C83 C77 C78 C79 1.1(8) . . . . ?
C76 C77 C78 C79 178.8(5) . . . . ?
C77 C78 C79 C81 -0.6(8) . . . . ?
C77 C78 C79 C80 -177.9(5) . . . . ?
C78 C79 C81 C82 0.7(8) . . . . ?
C80 C79 C81 C82 178.1(5) . . . . ?
C79 C81 C82 C83 -1.4(8) . . . . ?
C79 C81 C82 C84 -177.7(5) . . . . ?
C78 C77 C83 O6 179.4(5) . . . . ?
C76 C77 C83 O6 1.7(8) . . . . ?
C78 C77 C83 C82 -1.8(8) . . . . ?
C76 C77 C83 C82 -179.5(5) . . . . ?
C81 C82 C83 O6 -179.2(5) . . . . ?
C84 C82 C83 O6 -2.8(7) . . . . ?
C81 C82 C83 C77 1.9(8) . . . . ?
C84 C82 C83 C77 178.3(5) . . . . ?
C85 N11 C84 C82 177.1(5) . . . . ?
C81 C82 C84 N11 5.9(8) . . . . ?
C83 C82 C84 N11 -170.3(5) . . . . ?
C84 N11 C85 C90 124.7(5) . . . . ?
C84 N11 C85 C86 -114.5(5) . . . . ?
N11 C85 C86 C87 179.5(4) . . . . ?
C90 C85 C86 C87 -58.9(6) . . . . ?
C85 C86 C87 C88 56.6(6) . . . . ?
C86 C87 C88 C89 -53.7(6) . . . . ?
C87 C88 C89 C90 55.2(6) . . . . ?
C46 N12 C90 C85 121.6(5) . . . . ?
C46 N12 C90 C89 -120.0(5) . . . . ?
N11 C85 C90 N12 -63.6(5) . . . . ?
C86 C85 C90 N12 175.2(4) . . . . ?
N11 C85 C90 C89 179.4(4) . . . . ?
C86 C85 C90 C89 58.2(6) . . . . ?
C88 C89 C90 N12 -174.6(4) . . . . ?
C88 C89 C90 C85 -57.4(6) . . . . ?
