#------------------------------------------------------------------------------
#$Date: 2023-11-24 10:38:49 +0200 (Fri, 24 Nov 2023) $
#$Revision: 287771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/96/7119651.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_7119651
loop_
_publ_author_name
'U. B. Rao Khandavilli'
'Matteo Lusi'
'Balakrishna R. Bhogala'
'Anita R. Maguire'
'Matthias Stein'
'Simon E. Lawrence'
_publ_section_title
;
 Diversity in a simple co-crystal: racemic and kryptoracemic behaviour
;
_journal_name_full               Chem.Commun.
_journal_page_first              8309
_journal_page_last               8312
_journal_paper_doi               10.1039/C6CC04148E
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-05-16 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.913(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.882(4)
_cell_length_b                   20.953(8)
_cell_length_c                   16.215(6)
_cell_measurement_reflns_used    3281
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      3
_cell_volume                     3350(2)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.871
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.1597
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21286
_diffrn_reflns_point_group_measured_fraction_max 0.644
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.699
_diffrn_reflns_theta_min         2.675
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Flack x determined using 1578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     845
_refine_ls_number_reflns         10125
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.1089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1409P)²+8.3710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2653
_refine_ls_wR_factor_ref         0.3014
_reflns_Friedel_coverage         0.488
_reflns_Friedel_fraction_full    0.498
_reflns_Friedel_fraction_max     0.435
_reflns_number_gt                6088
_reflns_number_total             10125
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc04148e2.cif
_cod_data_source_block           Form_II
_cod_database_code               7119651
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1178(9) 0.5650(4) 0.9006(5) 0.036(2) Uani 1 1 d . . . . .
H1 H 0.1142 0.5287 0.8785 0.043 Uiso 1 1 calc R U . . .
O2 O 0.3019(8) 0.5790(3) 0.8283(5) 0.0286(18) Uani 1 1 d . . . . .
O3 O 0.3580(9) 0.6935(4) 0.7793(5) 0.039(2) Uani 1 1 d . . . . .
H3 H 0.3877 0.6578 0.7957 0.047 Uiso 1 1 calc R U . . .
O4 O 0.1524(8) 0.4422(3) 0.8952(5) 0.0241(17) Uani 1 1 d . . . . .
O5 O 0.6190(9) 0.2756(4) 0.8979(5) 0.036(2) Uani 1 1 d . . . . .
H5 H 0.6502 0.3127 0.9042 0.043 Uiso 1 1 calc R U . . .
O6 O 0.8193(8) 0.2575(4) 0.8465(5) 0.0278(18) Uani 1 1 d . . . . .
O7 O 0.9048(9) 0.1409(4) 0.8389(6) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.9057 0.1807 0.8326 0.048 Uiso 1 1 calc R U . . .
O8 O 0.6484(7) 0.3978(3) 0.8742(4) 0.0210(17) Uani 1 1 d . . . . .
O9 O 0.5924(8) 0.4356(3) 0.6365(5) 0.0276(18) Uani 1 1 d . . . . .
H9 H 0.6170 0.4730 0.6259 0.033 Uiso 1 1 calc R U . . .
O10 O 0.8124(8) 0.4136(4) 0.6255(5) 0.0278(18) Uani 1 1 d . . . . .
O11 O 0.8789(9) 0.2937(4) 0.6081(6) 0.043(2) Uani 1 1 d . . . . .
H11 H 0.8938 0.3331 0.6114 0.052 Uiso 1 1 calc R U . . .
O12 O 0.6402(7) 0.5550(3) 0.5887(4) 0.0217(17) Uani 1 1 d . . . . .
O13 O 0.0881(8) 0.7211(3) 0.6244(5) 0.0282(18) Uani 1 1 d . . . . .
H13 H 0.1085 0.6838 0.6110 0.034 Uiso 1 1 calc R U . . .
O14 O 0.2920(9) 0.7444(3) 0.5814(5) 0.0302(19) Uani 1 1 d . . . . .
O15 O 0.3512(9) 0.8608(3) 0.5445(5) 0.033(2) Uani 1 1 d . . . . .
H15 H 0.3573 0.8209 0.5408 0.039 Uiso 1 1 calc R U . . .
O16 O 0.1452(7) 0.6023(3) 0.5943(5) 0.0227(17) Uani 1 1 d . . . . .
N1 N 0.3731(9) 0.4457(4) 0.8689(5) 0.024(2) Uani 1 1 d . . . . .
H1A H 0.3638 0.4846 0.8490 0.029 Uiso 1 1 calc R U . . .
H1B H 0.4527 0.4267 0.8703 0.029 Uiso 1 1 calc R U . . .
N2 N 0.8726(9) 0.3937(4) 0.8573(5) 0.022(2) Uani 1 1 d . . . . .
H2A H 0.8658 0.3556 0.8346 0.026 Uiso 1 1 calc R U . . .
H2B H 0.9521 0.4126 0.8638 0.026 Uiso 1 1 calc R U . . .
N3 N 0.8648(9) 0.5504(4) 0.6061(5) 0.022(2) Uani 1 1 d . . . . .
H3A H 0.8622 0.5122 0.6285 0.027 Uiso 1 1 calc R U . . .
H3B H 0.9433 0.5691 0.6003 0.027 Uiso 1 1 calc R U . . .
N4 N 0.3708(9) 0.6104(4) 0.6102(5) 0.024(2) Uani 1 1 d . . . . .
H4A H 0.3671 0.6512 0.6228 0.028 Uiso 1 1 calc R U . . .
H4B H 0.4499 0.5912 0.6088 0.028 Uiso 1 1 calc R U . . .
C1 C 0.2081(12) 0.6006(5) 0.8648(6) 0.023(3) Uani 1 1 d . . . . .
C2 C 0.1830(11) 0.6705(5) 0.8726(6) 0.021(2) Uani 1 1 d . . . . .
C3 C 0.2604(12) 0.7129(5) 0.8275(7) 0.026(3) Uani 1 1 d . . . . .
C4 C 0.2349(13) 0.7775(5) 0.8333(7) 0.034(3) Uani 1 1 d . . . . .
H4 H 0.2827 0.8067 0.8012 0.041 Uiso 1 1 calc R U . . .
C5 C 0.1413(14) 0.7999(6) 0.8849(7) 0.038(3) Uani 1 1 d . . . . .
H2 H 0.1276 0.8446 0.8900 0.045 Uiso 1 1 calc R U . . .
C6 C 0.0672(15) 0.7584(6) 0.9295(8) 0.042(3) Uani 1 1 d . . . . .
H6 H 0.0009 0.7741 0.9641 0.050 Uiso 1 1 calc R U . . .
C7 C 0.0895(13) 0.6939(6) 0.9236(6) 0.031(3) Uani 1 1 d . . . . .
H8 H 0.0396 0.6651 0.9552 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2662(11) 0.4153(5) 0.8971(6) 0.021(2) Uani 1 1 d . . . . .
C9 C 0.2849(11) 0.3484(5) 0.9293(6) 0.021(2) Uani 1 1 d . . . . .
H10 H 0.3750 0.3328 0.9131 0.025 Uiso 1 1 calc R U . . .
C10 C 0.2890(11) 0.3497(4) 1.0256(6) 0.018(2) Uani 1 1 d . . . . .
C11 C 0.1929(13) 0.3789(5) 1.0654(6) 0.029(3) Uani 1 1 d . . . . .
H17 H 0.1240 0.4018 1.0343 0.035 Uiso 1 1 calc R U . . .
C12 C 0.1901(13) 0.3770(5) 1.1540(7) 0.032(3) Uani 1 1 d . . . . .
H12 H 0.1204 0.3975 1.1816 0.038 Uiso 1 1 calc R U . . .
C13 C 0.2957(14) 0.3432(6) 1.1981(7) 0.037(3) Uani 1 1 d . . . . .
H18 H 0.2997 0.3413 1.2567 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3914(13) 0.3134(5) 1.1556(7) 0.033(3) Uani 1 1 d . . . . .
H14 H 0.4605 0.2895 1.1852 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3908(12) 0.3170(5) 1.0699(7) 0.026(3) Uani 1 1 d . . . . .
H19 H 0.4606 0.2969 1.0419 0.031 Uiso 1 1 calc R U . . .
C16 C 0.1766(13) 0.3027(5) 0.8925(6) 0.024(3) Uani 1 1 d . . . . .
H16 H 0.0874 0.3161 0.9126 0.029 Uiso 1 1 calc R U . . .
C17 C 0.2030(14) 0.2340(5) 0.9196(7) 0.034(3) Uani 1 1 d . . . . .
H17A H 0.2896 0.2197 0.9001 0.052 Uiso 1 1 calc R U . . .
H17B H 0.1297 0.2067 0.8961 0.052 Uiso 1 1 calc R U . . .
H17C H 0.2065 0.2315 0.9801 0.052 Uiso 1 1 calc R U . . .
C18 C 0.1654(13) 0.3065(5) 0.7969(7) 0.032(3) Uani 1 1 d . . . . .
H18A H 0.1679 0.3512 0.7795 0.049 Uiso 1 1 calc R U . . .
H18B H 0.0798 0.2871 0.7755 0.049 Uiso 1 1 calc R U . . .
H18C H 0.2414 0.2834 0.7750 0.049 Uiso 1 1 calc R U . . .
C19 C 0.7153(12) 0.2372(5) 0.8766(6) 0.023(2) Uani 1 1 d . . . . .
C20 C 0.6930(12) 0.1703(5) 0.8931(6) 0.021(2) Uani 1 1 d . . . . .
C21 C 0.7906(11) 0.1238(5) 0.8726(6) 0.020(2) Uani 1 1 d . U . . .
C22 C 0.7645(11) 0.0596(5) 0.8871(6) 0.026(3) Uani 1 1 d . U . . .
H22 H 0.8284 0.0282 0.8730 0.031 Uiso 1 1 calc R U . . .
C23 C 0.6488(14) 0.0413(6) 0.9209(7) 0.034(3) Uani 1 1 d . . . . .
H23 H 0.6338 -0.0027 0.9309 0.041 Uiso 1 1 calc R U . . .
C24 C 0.5542(15) 0.0845(6) 0.9410(10) 0.051(4) Uani 1 1 d . . . . .
H24 H 0.4739 0.0710 0.9649 0.062 Uiso 1 1 calc R U . . .
C25 C 0.5765(14) 0.1490(6) 0.9259(7) 0.038(3) Uani 1 1 d . . . . .
H25 H 0.5093 0.1791 0.9388 0.046 Uiso 1 1 calc R U . . .
C26 C 0.7616(11) 0.4229(5) 0.8823(6) 0.020(2) Uani 1 1 d . . . . .
C27 C 0.7825(11) 0.4883(4) 0.9237(6) 0.017(2) Uani 1 1 d . . . . .
H27 H 0.8755 0.5037 0.9132 0.021 Uiso 1 1 calc R U . . .
C28 C 0.7759(12) 0.4788(5) 1.0169(6) 0.023(2) Uani 1 1 d . . . . .
C29 C 0.8806(12) 0.4989(5) 1.0707(7) 0.028(3) Uani 1 1 d . . . . .
H29 H 0.9579 0.5182 1.0495 0.034 Uiso 1 1 calc R U . . .
C30 C 0.8755(14) 0.4917(5) 1.1547(7) 0.034(3) Uani 1 1 d . . . . .
H30 H 0.9489 0.5058 1.1910 0.041 Uiso 1 1 calc R U . . .
C31 C 0.7600(13) 0.4632(5) 1.1866(7) 0.031(3) Uani 1 1 d . . . . .
H31 H 0.7548 0.4585 1.2446 0.037 Uiso 1 1 calc R U . . .
C32 C 0.6591(13) 0.4431(5) 1.1347(7) 0.027(3) Uani 1 1 d . . . . .
H32 H 0.5824 0.4234 1.1562 0.033 Uiso 1 1 calc R U . . .
C33 C 0.6630(14) 0.4502(5) 1.0502(7) 0.033(3) Uani 1 1 d . . . . .
H33 H 0.5892 0.4357 1.0144 0.039 Uiso 1 1 calc R U . . .
C34 C 0.6794(14) 0.5378(5) 0.8881(7) 0.030(3) Uani 1 1 d . . . . .
H34 H 0.5885 0.5266 0.9075 0.036 Uiso 1 1 calc R U . . .
C35 C 0.7180(13) 0.6045(5) 0.9213(7) 0.031(3) Uani 1 1 d . . . . .
H35A H 0.7281 0.6033 0.9819 0.047 Uiso 1 1 calc R U . . .
H35B H 0.6467 0.6350 0.9035 0.047 Uiso 1 1 calc R U . . .
H35C H 0.8039 0.6178 0.8998 0.047 Uiso 1 1 calc R U . . .
C36 C 0.6687(18) 0.5374(6) 0.7947(7) 0.053(4) Uani 1 1 d . . . . .
H36A H 0.7565 0.5490 0.7743 0.080 Uiso 1 1 calc R U . . .
H36B H 0.5998 0.5683 0.7744 0.080 Uiso 1 1 calc R U . . .
H36C H 0.6428 0.4946 0.7748 0.080 Uiso 1 1 calc R U . . .
C37 C 0.6994(13) 0.3960(5) 0.6353(6) 0.025(3) Uani 1 1 d . . . . .
C38 C 0.6629(12) 0.3283(5) 0.6511(6) 0.021(2) Uani 1 1 d . . . . .
C39 C 0.7542(11) 0.2811(5) 0.6330(7) 0.023(2) Uani 1 1 d . . . . .
C40 C 0.7224(12) 0.2170(5) 0.6404(7) 0.026(3) Uani 1 1 d . . . . .
H40 H 0.7837 0.1849 0.6253 0.032 Uiso 1 1 calc R U . . .
C41 C 0.5980(12) 0.2009(5) 0.6707(6) 0.029(3) Uani 1 1 d . . . . .
H41 H 0.5768 0.1572 0.6786 0.035 Uiso 1 1 calc R U . . .
C42 C 0.5051(12) 0.2471(5) 0.6894(7) 0.031(3) Uani 1 1 d . . . . .
H42 H 0.4208 0.2354 0.7099 0.037 Uiso 1 1 calc R U . . .
C43 C 0.5376(12) 0.3115(5) 0.6777(7) 0.028(3) Uani 1 1 d . . . . .
H43 H 0.4733 0.3438 0.6881 0.033 Uiso 1 1 calc R U . . .
C44 C 0.7511(11) 0.5796(5) 0.5815(6) 0.018(2) Uani 1 1 d . . . . .
C45 C 0.7701(12) 0.6456(5) 0.5444(6) 0.023(2) Uani 1 1 d . . . . .
H45 H 0.8586 0.6626 0.5687 0.027 Uiso 1 1 calc R U . . .
C46 C 0.7838(13) 0.6368(5) 0.4521(6) 0.027(3) Uani 1 1 d . . . . .
C47 C 0.6851(13) 0.6051(5) 0.4025(7) 0.032(3) Uani 1 1 d . . . . .
H47 H 0.6078 0.5879 0.4263 0.039 Uiso 1 1 calc R U . . .
C48 C 0.6990(14) 0.5984(5) 0.3195(6) 0.031(3) Uani 1 1 d . . . . .
H48 H 0.6313 0.5761 0.2866 0.037 Uiso 1 1 calc R U . . .
C49 C 0.8079(13) 0.6232(5) 0.2830(6) 0.033(3) Uani 1 1 d . . . . .
H49 H 0.8150 0.6182 0.2252 0.039 Uiso 1 1 calc R U . . .
C50 C 0.9096(13) 0.6561(5) 0.3306(8) 0.036(3) Uani 1 1 d . . . . .
H50 H 0.9863 0.6733 0.3061 0.043 Uiso 1 1 calc R U . . .
C51 C 0.8944(13) 0.6627(5) 0.4152(7) 0.031(3) Uani 1 1 d . . . . .
H51 H 0.9612 0.6854 0.4484 0.037 Uiso 1 1 calc R U . . .
C52 C 0.6598(12) 0.6930(5) 0.5659(6) 0.022(2) Uani 1 1 d . . . . .
H52 H 0.5709 0.6762 0.5419 0.026 Uiso 1 1 calc R U . . .
C53 C 0.6488(14) 0.7014(6) 0.6588(7) 0.036(3) Uani 1 1 d . . . . .
H53A H 0.6289 0.6601 0.6837 0.054 Uiso 1 1 calc R U . . .
H53B H 0.5757 0.7316 0.6684 0.054 Uiso 1 1 calc R U . . .
H53C H 0.7347 0.7180 0.6840 0.054 Uiso 1 1 calc R U . . .
C54 C 0.6834(15) 0.7579(5) 0.5261(8) 0.039(3) Uani 1 1 d . . . . .
H54A H 0.7674 0.7768 0.5509 0.058 Uiso 1 1 calc R U . . .
H54B H 0.6070 0.7863 0.5352 0.058 Uiso 1 1 calc R U . . .
H54C H 0.6910 0.7523 0.4665 0.058 Uiso 1 1 calc R U . . .
C55 C 0.1871(12) 0.7624(5) 0.6028(6) 0.022(2) Uani 1 1 d . . . . .
C56 C 0.1443(13) 0.8302(5) 0.6066(6) 0.025(3) Uani 1 1 d . . . . .
C57 C 0.2348(12) 0.8759(5) 0.5762(6) 0.023(2) Uani 1 1 d . . . . .
C58 C 0.1979(12) 0.9405(5) 0.5781(6) 0.027(3) Uani 1 1 d . . . . .
H58 H 0.2565 0.9720 0.5580 0.032 Uiso 1 1 calc R U . . .
C59 C 0.0769(12) 0.9585(5) 0.6089(6) 0.024(2) Uani 1 1 d . . . . .
H59 H 0.0529 1.0024 0.6095 0.028 Uiso 1 1 calc R U . . .
C60 C -0.0097(11) 0.9140(5) 0.6389(6) 0.024(2) Uani 1 1 d . . . . .
H60 H -0.0930 0.9269 0.6596 0.029 Uiso 1 1 calc R U . . .
C61 C 0.0263(13) 0.8495(5) 0.6386(6) 0.031(3) Uani 1 1 d . . . . .
H61 H -0.0317 0.8187 0.6608 0.037 Uiso 1 1 calc R U . . .
C62 C 0.2579(11) 0.5780(5) 0.5933(6) 0.019(2) Uani 1 1 d . U . . .
C63 C 0.2754(13) 0.5089(5) 0.5677(6) 0.028(3) Uani 1 1 d . . . . .
H63 H 0.3592 0.4932 0.5993 0.034 Uiso 1 1 calc R U . . .
C64 C 0.3056(11) 0.5072(5) 0.4757(6) 0.023(2) Uani 1 1 d . . . . .
C65 C 0.4008(11) 0.4674(5) 0.4475(6) 0.024(2) Uani 1 1 d . . . . .
H65 H 0.4518 0.4406 0.4853 0.029 Uiso 1 1 calc R U . . .
C66 C 0.4241(13) 0.4655(6) 0.3640(7) 0.035(3) Uani 1 1 d . . . . .
H66 H 0.4920 0.4378 0.3458 0.042 Uiso 1 1 calc R U . . .
C67 C 0.3524(10) 0.5023(5) 0.3081(6) 0.021(2) Uani 1 1 d . . . . .
H67 H 0.3703 0.5011 0.2512 0.025 Uiso 1 1 calc R U . . .
C68 C 0.2529(12) 0.5416(5) 0.3354(7) 0.026(3) Uani 1 1 d . . . . .
H68 H 0.1989 0.5664 0.2967 0.031 Uiso 1 1 calc R U . . .
C69 C 0.2307(12) 0.5451(5) 0.4194(7) 0.027(3) Uani 1 1 d . . . . .
H69 H 0.1643 0.5736 0.4380 0.033 Uiso 1 1 calc R U . . .
C70 C 0.1609(12) 0.4652(5) 0.5905(6) 0.025(3) Uani 1 1 d . . . . .
H70 H 0.0755 0.4799 0.5596 0.030 Uiso 1 1 calc R U . . .
C71 C 0.1869(11) 0.3958(5) 0.5649(7) 0.023(2) Uani 1 1 d . . . . .
H71A H 0.2757 0.3819 0.5891 0.035 Uiso 1 1 calc R U . . .
H71B H 0.1855 0.3930 0.5045 0.035 Uiso 1 1 calc R U . . .
H71C H 0.1161 0.3681 0.5848 0.035 Uiso 1 1 calc R U . . .
C72 C 0.1389(12) 0.4680(5) 0.6829(6) 0.027(3) Uani 1 1 d . . . . .
H72A H 0.0674 0.4378 0.6956 0.041 Uiso 1 1 calc R U . . .
H72B H 0.1119 0.5113 0.6976 0.041 Uiso 1 1 calc R U . . .
H72C H 0.2234 0.4566 0.7147 0.041 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C1 O1 H1 109.5 . .
C3 O3 H3 109.5 . .
C19 O5 H5 109.5 . .
C21 O7 H7 109.5 . .
C37 O9 H9 109.5 . .
C39 O11 H11 109.5 . .
C55 O13 H13 109.5 . .
C57 O15 H15 109.5 . .
C8 N1 H1A 120.0 . .
C8 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C26 N2 H2A 120.0 . .
C26 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
C44 N3 H3A 120.0 . .
C44 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
C62 N4 H4A 120.0 . .
C62 N4 H4B 120.0 . .
H4A N4 H4B 120.0 . .
O2 C1 O1 124.0(10) . .
O2 C1 C2 122.8(10) . .
O1 C1 C2 113.3(10) . .
C7 C2 C3 120.1(10) . .
C7 C2 C1 121.6(10) . .
C3 C2 C1 118.3(10) . .
O3 C3 C4 118.5(10) . .
O3 C3 C2 123.2(10) . .
C4 C3 C2 118.3(11) . .
C5 C4 C3 120.7(11) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4 C5 C6 120.6(12) . .
C4 C5 H2 119.7 . .
C6 C5 H2 119.7 . .
C7 C6 C5 119.6(12) . .
C7 C6 H6 120.2 . .
C5 C6 H6 120.2 . .
C2 C7 C6 120.7(11) . .
C2 C7 H8 119.7 . .
C6 C7 H8 119.7 . .
O4 C8 N1 120.2(9) . .
O4 C8 C9 121.1(9) . .
N1 C8 C9 118.7(9) . .
C8 C9 C16 112.5(8) . .
C8 C9 C10 109.1(8) . .
C16 C9 C10 111.8(9) . .
C8 C9 H10 107.8 . .
C16 C9 H10 107.8 . .
C10 C9 H10 107.8 . .
C11 C10 C15 119.6(10) . .
C11 C10 C9 121.5(10) . .
C15 C10 C9 118.8(9) . .
C10 C11 C12 122.3(11) . .
C10 C11 H17 118.9 . .
C12 C11 H17 118.9 . .
C13 C12 C11 117.0(11) . .
C13 C12 H12 121.5 . .
C11 C12 H12 121.5 . .
C14 C13 C12 119.2(10) . .
C14 C13 H18 120.4 . .
C12 C13 H18 120.4 . .
C13 C14 C15 121.7(11) . .
C13 C14 H14 119.1 . .
C15 C14 H14 119.1 . .
C10 C15 C14 120.0(11) . .
C10 C15 H19 120.0 . .
C14 C15 H19 120.0 . .
C17 C16 C9 112.2(9) . .
C17 C16 C18 109.6(9) . .
C9 C16 C18 111.1(9) . .
C17 C16 H16 107.9 . .
C9 C16 H16 107.9 . .
C18 C16 H16 107.9 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C18 H18A 109.5 . .
C16 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C16 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O6 C19 O5 121.8(10) . .
O6 C19 C20 123.0(10) . .
O5 C19 C20 115.1(10) . .
C25 C20 C21 117.8(10) . .
C25 C20 C19 121.8(10) . .
C21 C20 C19 120.4(10) . .
O7 C21 C22 120.0(10) . .
O7 C21 C20 121.0(10) . .
C22 C21 C20 119.0(10) . .
C23 C22 C21 120.8(10) . .
C23 C22 H22 119.6 . .
C21 C22 H22 119.6 . .
C22 C23 C24 121.4(11) . .
C22 C23 H23 119.3 . .
C24 C23 H23 119.3 . .
C23 C24 C25 119.0(13) . .
C23 C24 H24 120.5 . .
C25 C24 H24 120.5 . .
C20 C25 C24 121.9(12) . .
C20 C25 H25 119.0 . .
C24 C25 H25 119.0 . .
O8 C26 N2 121.7(9) . .
O8 C26 C27 121.4(9) . .
N2 C26 C27 116.8(9) . .
C28 C27 C26 107.6(8) . .
C28 C27 C34 112.8(9) . .
C26 C27 C34 111.8(8) . .
C28 C27 H27 108.2 . .
C26 C27 H27 108.2 . .
C34 C27 H27 108.2 . .
C29 C28 C33 118.1(10) . .
C29 C28 C27 120.4(10) . .
C33 C28 C27 121.5(10) . .
C28 C29 C30 121.3(11) . .
C28 C29 H29 119.4 . .
C30 C29 H29 119.4 . .
C29 C30 C31 119.5(11) . .
C29 C30 H30 120.2 . .
C31 C30 H30 120.2 . .
C32 C31 C30 119.4(11) . .
C32 C31 H31 120.3 . .
C30 C31 H31 120.3 . .
C31 C32 C33 121.6(12) . .
C31 C32 H32 119.2 . .
C33 C32 H32 119.2 . .
C32 C33 C28 120.2(11) . .
C32 C33 H33 119.9 . .
C28 C33 H33 119.9 . .
C36 C34 C27 111.8(10) . .
C36 C34 C35 110.8(9) . .
C27 C34 C35 109.8(9) . .
C36 C34 H34 108.1 . .
C27 C34 H34 108.1 . .
C35 C34 H34 108.1 . .
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 H36A 109.5 . .
C34 C36 H36B 109.5 . .
H36A C36 H36B 109.5 . .
C34 C36 H36C 109.5 . .
H36A C36 H36C 109.5 . .
H36B C36 H36C 109.5 . .
O10 C37 O9 123.6(10) . .
O10 C37 C38 123.7(10) . .
O9 C37 C38 112.7(10) . .
C39 C38 C43 119.7(10) . .
C39 C38 C37 118.4(10) . .
C43 C38 C37 121.8(10) . .
O11 C39 C38 123.1(10) . .
O11 C39 C40 115.6(9) . .
C38 C39 C40 121.2(10) . .
C39 C40 C41 118.4(10) . .
C39 C40 H40 120.8 . .
C41 C40 H40 120.8 . .
C42 C41 C40 121.5(10) . .
C42 C41 H41 119.3 . .
C40 C41 H41 119.3 . .
C41 C42 C43 118.8(11) . .
C41 C42 H42 120.6 . .
C43 C42 H42 120.6 . .
C38 C43 C42 120.2(11) . .
C38 C43 H43 119.9 . .
C42 C43 H43 119.9 . .
O12 C44 N3 121.7(9) . .
O12 C44 C45 123.8(9) . .
N3 C44 C45 114.6(9) . .
C46 C45 C44 107.4(8) . .
C46 C45 C52 114.4(9) . .
C44 C45 C52 112.9(8) . .
C46 C45 H45 107.2 . .
C44 C45 H45 107.2 . .
C52 C45 H45 107.2 . .
C47 C46 C51 118.6(10) . .
C47 C46 C45 121.4(10) . .
C51 C46 C45 120.0(10) . .
C48 C47 C46 120.3(12) . .
C48 C47 H47 119.9 . .
C46 C47 H47 119.9 . .
C49 C48 C47 121.5(11) . .
C49 C48 H48 119.3 . .
C47 C48 H48 119.3 . .
C48 C49 C50 120.2(10) . .
C48 C49 H49 119.9 . .
C50 C49 H49 119.9 . .
C51 C50 C49 117.8(11) . .
C51 C50 H50 121.1 . .
C49 C50 H50 121.1 . .
C46 C51 C50 121.6(12) . .
C46 C51 H51 119.2 . .
C50 C51 H51 119.2 . .
C53 C52 C54 109.7(9) . .
C53 C52 C45 113.5(9) . .
C54 C52 C45 110.4(9) . .
C53 C52 H52 107.7 . .
C54 C52 H52 107.7 . .
C45 C52 H52 107.7 . .
C52 C53 H53A 109.5 . .
C52 C53 H53B 109.5 . .
H53A C53 H53B 109.5 . .
C52 C53 H53C 109.5 . .
H53A C53 H53C 109.5 . .
H53B C53 H53C 109.5 . .
C52 C54 H54A 109.5 . .
C52 C54 H54B 109.5 . .
H54A C54 H54B 109.5 . .
C52 C54 H54C 109.5 . .
H54A C54 H54C 109.5 . .
H54B C54 H54C 109.5 . .
O14 C55 O13 122.1(10) . .
O14 C55 C56 125.3(10) . .
O13 C55 C56 112.5(10) . .
C61 C56 C57 120.3(10) . .
C61 C56 C55 123.5(10) . .
C57 C56 C55 116.2(10) . .
O15 C57 C58 118.1(10) . .
O15 C57 C56 123.7(10) . .
C58 C57 C56 118.2(11) . .
C59 C58 C57 120.3(10) . .
C59 C58 H58 119.8 . .
C57 C58 H58 119.8 . .
C60 C59 C58 121.1(10) . .
C60 C59 H59 119.4 . .
C58 C59 H59 119.4 . .
C59 C60 C61 119.3(11) . .
C59 C60 H60 120.3 . .
C61 C60 H60 120.3 . .
C56 C61 C60 120.7(11) . .
C56 C61 H61 119.6 . .
C60 C61 H61 119.6 . .
O16 C62 N4 122.7(9) . .
O16 C62 C63 121.4(9) . .
N4 C62 C63 115.9(10) . .
C62 C63 C70 114.0(10) . .
C62 C63 C64 108.7(8) . .
C70 C63 C64 114.7(9) . .
C62 C63 H63 106.3 . .
C70 C63 H63 106.3 . .
C64 C63 H63 106.3 . .
C65 C64 C69 118.8(10) . .
C65 C64 C63 121.6(10) . .
C69 C64 C63 119.6(9) . .
C64 C65 C66 120.6(11) . .
C64 C65 H65 119.7 . .
C66 C65 H65 119.7 . .
C67 C66 C65 121.6(12) . .
C67 C66 H66 119.2 . .
C65 C66 H66 119.2 . .
C66 C67 C68 118.5(10) . .
C66 C67 H67 120.8 . .
C68 C67 H67 120.8 . .
C67 C68 C69 120.6(10) . .
C67 C68 H68 119.7 . .
C69 C68 H68 119.7 . .
C64 C69 C68 119.9(10) . .
C64 C69 H69 120.0 . .
C68 C69 H69 120.0 . .
C63 C70 C72 111.9(9) . .
C63 C70 C71 111.3(9) . .
C72 C70 C71 109.7(8) . .
C63 C70 H70 107.9 . .
C72 C70 H70 107.9 . .
C71 C70 H70 107.9 . .
C70 C71 H71A 109.5 . .
C70 C71 H71B 109.5 . .
H71A C71 H71B 109.5 . .
C70 C71 H71C 109.5 . .
H71A C71 H71C 109.5 . .
H71B C71 H71C 109.5 . .
C70 C72 H72A 109.5 . .
C70 C72 H72B 109.5 . .
H72A C72 H72B 109.5 . .
C70 C72 H72C 109.5 . .
H72A C72 H72C 109.5 . .
H72B C72 H72C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.327(13) .
O1 H1 0.8400 .
O2 C1 1.221(13) .
O3 C3 1.345(13) .
O3 H3 0.8400 .
O4 C8 1.256(12) .
O5 C19 1.311(13) .
O5 H5 0.8400 .
O6 C19 1.243(13) .
O7 C21 1.335(13) .
O7 H7 0.8400 .
O8 C26 1.235(12) .
O9 C37 1.345(13) .
O9 H9 0.8400 .
O10 C37 1.196(14) .
O11 C39 1.348(14) .
O11 H11 0.8400 .
O12 C44 1.224(12) .
O13 C55 1.370(13) .
O13 H13 0.8400 .
O14 C55 1.177(13) .
O15 C57 1.329(13) .
O15 H15 0.8400 .
O16 C62 1.226(12) .
N1 C8 1.340(13) .
N1 H1A 0.8800 .
N1 H1B 0.8800 .
N2 C26 1.342(13) .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
N3 C44 1.318(13) .
N3 H3A 0.8800 .
N3 H3B 0.8800 .
N4 C62 1.319(13) .
N4 H4A 0.8800 .
N4 H4B 0.8800 .
C1 C2 1.492(14) .
C2 C7 1.372(15) .
C2 C3 1.409(15) .
C3 C4 1.382(15) .
C4 C5 1.373(18) .
C4 H4 0.9500 .
C5 C6 1.374(17) .
C5 H2 0.9500 .
C6 C7 1.373(16) .
C6 H6 0.9500 .
C7 H8 0.9500 .
C8 C9 1.503(14) .
C9 C16 1.526(15) .
C9 C10 1.559(13) .
C9 H10 1.0000 .
C10 C11 1.333(15) .
C10 C15 1.378(14) .
C11 C12 1.439(14) .
C11 H17 0.9500 .
C12 C13 1.414(17) .
C12 H12 0.9500 .
C13 C14 1.360(18) .
C13 H18 0.9500 .
C14 C15 1.391(15) .
C14 H14 0.9500 .
C15 H19 0.9500 .
C16 C17 1.522(15) .
C16 C18 1.549(14) .
C16 H16 1.0000 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 C20 1.447(15) .
C20 C25 1.376(16) .
C20 C21 1.425(14) .
C21 C22 1.392(15) .
C22 C23 1.357(16) .
C22 H22 0.9500 .
C23 C24 1.358(18) .
C23 H23 0.9500 .
C24 C25 1.393(17) .
C24 H24 0.9500 .
C25 H25 0.9500 .
C26 C27 1.534(13) .
C27 C28 1.531(14) .
C27 C34 1.537(15) .
C27 H27 1.0000 .
C28 C29 1.373(15) .
C28 C33 1.405(17) .
C29 C30 1.374(16) .
C29 H29 0.9500 .
C30 C31 1.417(18) .
C30 H30 0.9500 .
C31 C32 1.329(16) .
C31 H31 0.9500 .
C32 C33 1.381(15) .
C32 H32 0.9500 .
C33 H33 0.9500 .
C34 C36 1.511(16) .
C34 C35 1.537(15) .
C34 H34 1.0000 .
C35 H35A 0.9800 .
C35 H35B 0.9800 .
C35 H35C 0.9800 .
C36 H36A 0.9800 .
C36 H36B 0.9800 .
C36 H36C 0.9800 .
C37 C38 1.490(15) .
C38 C39 1.383(14) .
C38 C43 1.384(16) .
C39 C40 1.387(15) .
C40 C41 1.395(16) .
C40 H40 0.9500 .
C41 C42 1.382(16) .
C41 H41 0.9500 .
C42 C43 1.404(15) .
C42 H42 0.9500 .
C43 H43 0.9500 .
C44 C45 1.524(14) .
C45 C46 1.524(14) .
C45 C52 1.532(14) .
C45 H45 1.0000 .
C46 C47 1.390(16) .
C46 C51 1.391(16) .
C47 C48 1.369(15) .
C47 H47 0.9500 .
C48 C49 1.367(17) .
C48 H48 0.9500 .
C49 C50 1.406(17) .
C49 H49 0.9500 .
C50 C51 1.398(16) .
C50 H50 0.9500 .
C51 H51 0.9500 .
C52 C53 1.528(14) .
C52 C54 1.530(14) .
C52 H52 1.0000 .
C53 H53A 0.9800 .
C53 H53B 0.9800 .
C53 H53C 0.9800 .
C54 H54A 0.9800 .
C54 H54B 0.9800 .
C54 H54C 0.9800 .
C55 C56 1.485(14) .
C56 C61 1.368(16) .
C56 C57 1.422(15) .
C57 C58 1.404(15) .
C58 C59 1.379(16) .
C58 H58 0.9500 .
C59 C60 1.378(15) .
C59 H59 0.9500 .
C60 C61 1.397(15) .
C60 H60 0.9500 .
C61 H61 0.9500 .
C62 C63 1.518(14) .
C63 C70 1.522(16) .
C63 C64 1.542(14) .
C63 H63 1.0000 .
C64 C65 1.358(14) .
C64 C69 1.386(15) .
C65 C66 1.390(14) .
C65 H65 0.9500 .
C66 C67 1.353(16) .
C66 H66 0.9500 .
C67 C68 1.379(15) .
C67 H67 0.9500 .
C68 C69 1.396(15) .
C68 H68 0.9500 .
C69 H69 0.9500 .
C70 C72 1.530(13) .
C70 C71 1.539(14) .
C70 H70 1.0000 .
C71 H71A 0.9800 .
C71 H71B 0.9800 .
C71 H71C 0.9800 .
C72 H72A 0.9800 .
C72 H72B 0.9800 .
C72 H72C 0.9800 .
