#------------------------------------------------------------------------------
#$Date: 2020-07-06 04:45:24 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126566.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_7126566
loop_
_publ_author_name
'Gao, Zeng'
'Qian, Jinlong'
'Yang, Huameng'
'Hang, Xiao-Chun'
'Zhang, Jinlong'
'Jiang, Gaoxi'
_publ_section_title
;
 Chiral Brønsted acid-catalyzed dynamic kinetic resolution of
 atropisomeric ortho-formyl naphthamides.
;
_journal_issue                   53
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7265
_journal_page_last               7268
_journal_paper_doi               10.1039/d0cc02380a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_sum            'C28 H29 N3 O'
_chemical_formula_weight         423.54
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc23xyqq
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-11-18 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.131(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0096(13)
_cell_length_b                   13.3196(14)
_cell_length_c                   16.1216(17)
_cell_measurement_reflns_used    3658
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.73
_cell_measurement_theta_min      2.36
_cell_volume                     2436.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12578
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.125
_diffrn_reflns_theta_max         25.125
_diffrn_reflns_theta_min         1.337
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.6692
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 2227 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     585
_refine_ls_number_reflns         8134
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0427
_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)+(0.0500P)²+0.1587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    0.868
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                6147
_reflns_number_total             8134
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02380a2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7126565--7126566.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7126566
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.986
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
C1 C 0.5987(3) 0.2761(3) 1.1032(2) 0.0546(8) Uani 1 1 d . . . . .
C2 C 0.7025(3) 0.3261(3) 1.1496(2) 0.0737(11) Uani 1 1 d . . . . .
H2 H 0.7118 0.3936 1.1387 0.088 Uiso 1 1 calc R U . . .
C3 C 0.7921(3) 0.2743(4) 1.2121(3) 0.0861(13) Uani 1 1 d . . . . .
H3 H 0.8615 0.3076 1.2427 0.103 Uiso 1 1 calc R U . . .
C4 C 0.7794(3) 0.1752(4) 1.2291(3) 0.0841(12) Uani 1 1 d . . . . .
H4 H 0.8404 0.1412 1.2704 0.101 Uiso 1 1 calc R U . . .
C5 C 0.6768(3) 0.1262(3) 1.1852(2) 0.0662(10) Uani 1 1 d . . . . .
H5 H 0.6674 0.0591 1.1974 0.079 Uiso 1 1 calc R U . . .
C6 C 0.5870(3) 0.1762(3) 1.1226(2) 0.0528(8) Uani 1 1 d . . . . .
C7 C 0.4503(3) 0.0285(3) 1.0757(2) 0.0639(9) Uani 1 1 d . . . . .
H7 H 0.4985 -0.0220 1.1084 0.077 Uiso 1 1 calc R U . . .
C8 C 0.3389(3) 0.0165(3) 1.0210(3) 0.0670(10) Uani 1 1 d . . . . .
H8 H 0.2970 -0.0434 1.0096 0.080 Uiso 1 1 calc R U . . .
C9 C 0.2974(3) 0.1106(3) 0.9842(3) 0.0663(10) Uani 1 1 d . . . . .
H9 H 0.2234 0.1241 0.9439 0.080 Uiso 1 1 calc R U . . .
C10 C 0.3853(3) 0.1783(2) 1.0183(2) 0.0512(8) Uani 1 1 d . . . . .
C11 C 0.3884(2) 0.2899(2) 1.0093(2) 0.0505(8) Uani 1 1 d . . . . .
H11 H 0.3511 0.3209 1.0486 0.061 Uiso 1 1 calc R U . . .
C12 C 0.3228(2) 0.3221(2) 0.9157(2) 0.0465(7) Uani 1 1 d . . . . .
C13 C 0.3719(3) 0.3035(3) 0.8491(2) 0.0567(8) Uani 1 1 d . . . . .
H13 H 0.4464 0.2749 0.8636 0.068 Uiso 1 1 calc R U . . .
C14 C 0.3127(3) 0.3264(3) 0.7639(2) 0.0602(9) Uani 1 1 d . . . . .
H14 H 0.3480 0.3143 0.7214 0.072 Uiso 1 1 calc R U . . .
C15 C 0.1982(3) 0.3683(3) 0.7386(2) 0.0564(8) Uani 1 1 d . . . . .
C16 C 0.1336(4) 0.3904(3) 0.6496(2) 0.0772(11) Uani 1 1 d . . . . .
H16 H 0.1671 0.3783 0.6060 0.093 Uiso 1 1 calc R U . . .
C17 C 0.0240(5) 0.4288(4) 0.6281(3) 0.0964(15) Uani 1 1 d . . . . .
H17 H -0.0178 0.4421 0.5695 0.116 Uiso 1 1 calc R U . . .
C18 C -0.0286(4) 0.4491(4) 0.6924(3) 0.0889(13) Uani 1 1 d . . . . .
H18 H -0.1041 0.4760 0.6763 0.107 Uiso 1 1 calc R U . . .
C19 C 0.0319(3) 0.4291(3) 0.7789(2) 0.0668(10) Uani 1 1 d . . . . .
H19 H -0.0031 0.4425 0.8213 0.080 Uiso 1 1 calc R U . . .
C20 C 0.1470(3) 0.3882(2) 0.8043(2) 0.0499(8) Uani 1 1 d . . . . .
C21 C 0.2116(2) 0.3634(2) 0.89425(19) 0.0449(7) Uani 1 1 d . . . . .
C22 C 0.1486(3) 0.3690(3) 0.9612(2) 0.0509(8) Uani 1 1 d . . . . .
C23 C 0.0991(3) 0.4558(4) 1.0782(3) 0.0771(11) Uani 1 1 d . . . . .
H23 H 0.1181 0.5213 1.1071 0.093 Uiso 1 1 calc R U . . .
C24 C -0.0346(3) 0.4507(5) 1.0385(3) 0.1021(16) Uani 1 1 d . . . . .
H24A H -0.0615 0.5012 0.9939 0.153 Uiso 1 1 calc R U . . .
H24B H -0.0693 0.4621 1.0835 0.153 Uiso 1 1 calc R U . . .
H24C H -0.0574 0.3856 1.0130 0.153 Uiso 1 1 calc R U . . .
C25 C 0.1472(4) 0.3770(5) 1.1487(3) 0.1088(17) Uani 1 1 d . . . . .
H25A H 0.1323 0.3114 1.1227 0.163 Uiso 1 1 calc R U . . .
H25B H 0.1093 0.3833 1.1924 0.163 Uiso 1 1 calc R U . . .
H25C H 0.2306 0.3864 1.1756 0.163 Uiso 1 1 calc R U . . .
C26 C 0.2234(4) 0.5417(3) 0.9993(3) 0.0779(11) Uani 1 1 d . . . . .
H26 H 0.2553 0.5266 0.9520 0.093 Uiso 1 1 calc R U . . .
C27 C 0.3282(4) 0.5646(4) 1.0808(3) 0.1017(15) Uani 1 1 d . . . . .
H27A H 0.3006 0.5796 1.1290 0.153 Uiso 1 1 calc R U . . .
H27B H 0.3705 0.6212 1.0695 0.153 Uiso 1 1 calc R U . . .
H27C H 0.3794 0.5073 1.0952 0.153 Uiso 1 1 calc R U . . .
C28 C 0.1422(5) 0.6320(4) 0.9694(4) 0.1124(17) Uani 1 1 d . . . . .
H28A H 0.0841 0.6176 0.9135 0.169 Uiso 1 1 calc R U . . .
H28B H 0.1876 0.6894 0.9639 0.169 Uiso 1 1 calc R U . . .
H28C H 0.1037 0.6458 1.0117 0.169 Uiso 1 1 calc R U . . .
C29 C 0.7926(3) 0.0689(3) 0.6649(2) 0.0584(9) Uani 1 1 d . . . . .
C30 C 0.8559(4) -0.0034(3) 0.6369(3) 0.0769(11) Uani 1 1 d . . . . .
H30 H 0.8162 -0.0502 0.5947 0.092 Uiso 1 1 calc R U . . .
C31 C 0.9774(4) -0.0060(4) 0.6714(3) 0.0920(14) Uani 1 1 d . . . . .
H31 H 1.0191 -0.0547 0.6525 0.110 Uiso 1 1 calc R U . . .
C32 C 1.0375(4) 0.0631(4) 0.7336(3) 0.0906(14) Uani 1 1 d . . . . .
H32 H 1.1192 0.0599 0.7574 0.109 Uiso 1 1 calc R U . . .
C33 C 0.9765(3) 0.1367(3) 0.7606(3) 0.0756(11) Uani 1 1 d . . . . .
H33 H 1.0172 0.1845 0.8014 0.091 Uiso 1 1 calc R U . . .
C34 C 0.8553(3) 0.1398(3) 0.7273(2) 0.0579(9) Uani 1 1 d . . . . .
C35 C 0.8211(3) 0.2765(3) 0.8238(2) 0.0658(9) Uani 1 1 d . . . . .
H35 H 0.8953 0.2795 0.8663 0.079 Uiso 1 1 calc R U . . .
C36 C 0.7281(3) 0.3341(3) 0.8206(3) 0.0757(11) Uani 1 1 d . . . . .
H36 H 0.7266 0.3844 0.8603 0.091 Uiso 1 1 calc R U . . .
C37 C 0.6325(3) 0.3047(3) 0.7461(2) 0.0664(10) Uani 1 1 d . . . . .
H37 H 0.5571 0.3319 0.7282 0.080 Uiso 1 1 calc R U . . .
C38 C 0.6712(3) 0.2299(3) 0.7058(2) 0.0523(8) Uani 1 1 d . . . . .
C39 C 0.6175(3) 0.1724(3) 0.6224(2) 0.0548(8) Uani 1 1 d . . . . .
H39 H 0.6385 0.2055 0.5753 0.066 Uiso 1 1 calc R U . . .
C40 C 0.4849(3) 0.1668(3) 0.5963(2) 0.0525(8) Uani 1 1 d . . . . .
C41 C 0.4334(3) 0.1197(3) 0.6536(2) 0.0617(9) Uani 1 1 d . . . . .
H41 H 0.4814 0.0925 0.7063 0.074 Uiso 1 1 calc R U . . .
C42 C 0.3142(3) 0.1140(3) 0.6321(3) 0.0666(10) Uani 1 1 d . . . . .
H42 H 0.2821 0.0839 0.6711 0.080 Uiso 1 1 calc R U . . .
C43 C 0.2386(3) 0.1522(3) 0.5527(3) 0.0645(10) Uani 1 1 d . . . . .
C44 C 0.1136(4) 0.1474(4) 0.5281(3) 0.0877(13) Uani 1 1 d . . . . .
H44 H 0.0790 0.1184 0.5661 0.105 Uiso 1 1 calc R U . . .
C45 C 0.0443(4) 0.1846(4) 0.4502(4) 0.1026(16) Uani 1 1 d . . . . .
H45 H -0.0372 0.1811 0.4356 0.123 Uiso 1 1 calc R U . . .
C46 C 0.0931(4) 0.2276(4) 0.3922(4) 0.1062(17) Uani 1 1 d . . . . .
H46 H 0.0441 0.2515 0.3384 0.127 Uiso 1 1 calc R U . . .
C47 C 0.2127(3) 0.2354(3) 0.4129(3) 0.0815(12) Uani 1 1 d . . . . .
H47 H 0.2445 0.2645 0.3732 0.098 Uiso 1 1 calc R U . . .
C48 C 0.2884(3) 0.1993(3) 0.4946(2) 0.0608(9) Uani 1 1 d . . . . .
C49 C 0.4140(3) 0.2068(2) 0.5183(2) 0.0523(8) Uani 1 1 d . . . . .
C50 C 0.4646(3) 0.2687(3) 0.4603(2) 0.0571(8) Uani 1 1 d . . . . .
C51 C 0.4909(4) 0.1107(3) 0.3872(3) 0.0868(13) Uani 1 1 d . . . . .
H51 H 0.4563 0.0839 0.4299 0.104 Uiso 1 1 calc R U . . .
C52 C 0.6077(5) 0.0560(4) 0.4018(3) 0.1118(17) Uani 1 1 d . . . . .
H52A H 0.6336 0.0665 0.3521 0.168 Uiso 1 1 calc R U . . .
H52B H 0.5971 -0.0146 0.4088 0.168 Uiso 1 1 calc R U . . .
H52C H 0.6659 0.0817 0.4537 0.168 Uiso 1 1 calc R U . . .
C53 C 0.4030(5) 0.0908(4) 0.2957(3) 0.127(2) Uani 1 1 d . . . . .
H53A H 0.3307 0.1257 0.2893 0.191 Uiso 1 1 calc R U . . .
H53B H 0.3878 0.0201 0.2882 0.191 Uiso 1 1 calc R U . . .
H53C H 0.4354 0.1143 0.2521 0.191 Uiso 1 1 calc R U . . .
C54 C 0.5665(4) 0.2772(3) 0.3503(3) 0.0772(11) Uani 1 1 d . . . . .
H54 H 0.5928 0.2277 0.3158 0.093 Uiso 1 1 calc R U . . .
C55 C 0.6767(4) 0.3297(4) 0.4086(4) 0.1056(16) Uani 1 1 d . . . . .
H55A H 0.6552 0.3793 0.4437 0.158 Uiso 1 1 calc R U . . .
H55B H 0.7163 0.3616 0.3727 0.158 Uiso 1 1 calc R U . . .
H55C H 0.7284 0.2812 0.4462 0.158 Uiso 1 1 calc R U . . .
C56 C 0.4814(5) 0.3473(4) 0.2843(3) 0.0991(15) Uani 1 1 d . . . . .
H56A H 0.4150 0.3095 0.2483 0.149 Uiso 1 1 calc R U . . .
H56B H 0.5210 0.3780 0.2478 0.149 Uiso 1 1 calc R U . . .
H56C H 0.4546 0.3985 0.3152 0.149 Uiso 1 1 calc R U . . .
N1 N 0.5118(2) 0.3224(2) 1.03511(19) 0.0617(8) Uani 1 1 d . . . . .
H1 H 0.5307 0.3712 1.0074 0.074 Uiso 1 1 calc R U . . .
N2 N 0.4804(2) 0.1274(2) 1.07483(17) 0.0511(6) Uani 1 1 d . . . . .
N3 N 0.1582(2) 0.4518(2) 1.01076(18) 0.0593(7) Uani 1 1 d . . . . .
N4 N 0.5070(3) 0.2198(2) 0.40310(19) 0.0644(8) Uani 1 1 d . . . . .
N5 N 0.7875(2) 0.2122(2) 0.75324(18) 0.0555(7) Uani 1 1 d . . . . .
N6 N 0.6701(2) 0.0716(2) 0.63636(19) 0.0619(7) Uani 1 1 d . . . . .
H6 H 0.6281 0.0179 0.6275 0.074 Uiso 1 1 calc R U . . .
O1 O 0.08956(19) 0.29519(19) 0.96735(16) 0.0647(6) Uani 1 1 d . . . . .
O2 O 0.4664(2) 0.36013(19) 0.46760(16) 0.0718(7) Uani 1 1 d . . . . .
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
_geom_angle_publ_flag
C6 C1 N1 120.0(3) . . ?
C6 C1 C2 118.5(3) . . ?
N1 C1 C2 121.4(3) . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 N2 121.7(3) . . ?
C1 C6 N2 117.3(3) . . ?
C8 C7 N2 108.4(3) . . ?
C8 C7 H7 125.8 . . ?
N2 C7 H7 125.8 . . ?
C7 C8 C9 108.0(3) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
C10 C9 C8 107.4(3) . . ?
C10 C9 H9 126.3 . . ?
C8 C9 H9 126.3 . . ?
C9 C10 N2 107.8(3) . . ?
C9 C10 C11 131.4(3) . . ?
N2 C10 C11 120.6(3) . . ?
N1 C11 C10 108.7(3) . . ?
N1 C11 C12 110.2(3) . . ?
C10 C11 C12 110.9(3) . . ?
N1 C11 H11 109.0 . . ?
C10 C11 H11 109.0 . . ?
C12 C11 H11 109.0 . . ?
C21 C12 C13 119.4(3) . . ?
C21 C12 C11 120.5(3) . . ?
C13 C12 C11 119.9(3) . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C20 118.6(3) . . ?
C14 C15 C16 122.0(3) . . ?
C20 C15 C16 119.4(3) . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 121.4(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.7(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 118.6(3) . . ?
C15 C20 C21 119.2(3) . . ?
C19 C20 C21 122.2(3) . . ?
C12 C21 C20 120.1(3) . . ?
C12 C21 C22 120.7(3) . . ?
C20 C21 C22 118.5(3) . . ?
O1 C22 N3 123.0(3) . . ?
O1 C22 C21 117.0(3) . . ?
N3 C22 C21 120.0(3) . . ?
N3 C23 C25 111.6(3) . . ?
N3 C23 C24 112.5(3) . . ?
C25 C23 C24 112.0(4) . . ?
N3 C23 H23 106.8 . . ?
C25 C23 H23 106.8 . . ?
C24 C23 H23 106.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N3 C26 C27 112.1(4) . . ?
N3 C26 C28 111.7(3) . . ?
C27 C26 C28 112.2(4) . . ?
N3 C26 H26 106.8 . . ?
C27 C26 H26 106.8 . . ?
C28 C26 H26 106.8 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N6 C29 C30 122.8(4) . . ?
N6 C29 C34 118.7(3) . . ?
C30 C29 C34 118.5(3) . . ?
C31 C30 C29 120.2(4) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C32 C31 C30 120.6(4) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C33 120.0(4) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 C32 120.0(4) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C29 120.7(3) . . ?
C33 C34 N5 122.9(4) . . ?
C29 C34 N5 116.5(3) . . ?
C36 C35 N5 108.0(3) . . ?
C36 C35 H35 126.0 . . ?
N5 C35 H35 126.0 . . ?
C35 C36 C37 107.8(3) . . ?
C35 C36 H36 126.1 . . ?
C37 C36 H36 126.1 . . ?
C38 C37 C36 107.5(3) . . ?
C38 C37 H37 126.3 . . ?
C36 C37 H37 126.3 . . ?
C37 C38 N5 107.8(3) . . ?
C37 C38 C39 133.9(3) . . ?
N5 C38 C39 118.2(3) . . ?
N6 C39 C38 107.0(3) . . ?
N6 C39 C40 111.1(3) . . ?
C38 C39 C40 112.4(3) . . ?
N6 C39 H39 108.8 . . ?
C38 C39 H39 108.8 . . ?
C40 C39 H39 108.8 . . ?
C49 C40 C41 119.8(3) . . ?
C49 C40 C39 121.1(3) . . ?
C41 C40 C39 119.1(3) . . ?
C42 C41 C40 120.4(3) . . ?
C42 C41 H41 119.8 . . ?
C40 C41 H41 119.8 . . ?
C41 C42 C43 121.8(4) . . ?
C41 C42 H42 119.1 . . ?
C43 C42 H42 119.1 . . ?
C42 C43 C48 118.6(3) . . ?
C42 C43 C44 123.3(4) . . ?
C48 C43 C44 118.2(4) . . ?
C45 C44 C43 121.0(5) . . ?
C45 C44 H44 119.5 . . ?
C43 C44 H44 119.5 . . ?
C44 C45 C46 120.8(4) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C47 C46 C45 120.7(5) . . ?
C47 C46 H46 119.6 . . ?
C45 C46 H46 119.6 . . ?
C46 C47 C48 120.2(5) . . ?
C46 C47 H47 119.9 . . ?
C48 C47 H47 119.9 . . ?
C43 C48 C47 119.1(3) . . ?
C43 C48 C49 119.5(3) . . ?
C47 C48 C49 121.5(4) . . ?
C40 C49 C48 119.9(3) . . ?
C40 C49 C50 121.5(3) . . ?
C48 C49 C50 118.3(3) . . ?
O2 C50 N4 123.0(3) . . ?
O2 C50 C49 118.7(3) . . ?
N4 C50 C49 118.2(3) . . ?
N4 C51 C52 112.4(4) . . ?
N4 C51 C53 110.3(4) . . ?
C52 C51 C53 112.0(4) . . ?
N4 C51 H51 107.3 . . ?
C52 C51 H51 107.3 . . ?
C53 C51 H51 107.3 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
N4 C54 C55 111.5(3) . . ?
N4 C54 C56 112.0(3) . . ?
C55 C54 C56 113.5(4) . . ?
N4 C54 H54 106.4 . . ?
C55 C54 H54 106.4 . . ?
C56 C54 H54 106.4 . . ?
C54 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C54 C56 H56A 109.5 . . ?
C54 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C54 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C1 N1 C11 121.4(3) . . ?
C1 N1 H1 119.3 . . ?
C11 N1 H1 119.3 . . ?
C7 N2 C10 108.4(3) . . ?
C7 N2 C6 129.1(3) . . ?
C10 N2 C6 122.5(3) . . ?
C22 N3 C26 122.5(3) . . ?
C22 N3 C23 119.8(3) . . ?
C26 N3 C23 117.7(3) . . ?
C50 N4 C51 122.2(3) . . ?
C50 N4 C54 119.9(3) . . ?
C51 N4 C54 117.8(3) . . ?
C35 N5 C38 108.8(3) . . ?
C35 N5 C34 129.0(3) . . ?
C38 N5 C34 122.1(3) . . ?
C29 N6 C39 115.5(3) . . ?
C29 N6 H6 122.3 . . ?
C39 N6 H6 122.3 . . ?
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
C1 C6 1.385(5) . ?
C1 N1 1.386(4) . ?
C1 C2 1.395(5) . ?
C2 C3 1.392(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 N2 1.417(4) . ?
C7 C8 1.349(5) . ?
C7 N2 1.368(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.407(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.360(5) . ?
C9 H9 0.9300 . ?
C10 N2 1.383(4) . ?
C10 C11 1.494(5) . ?
C11 N1 1.468(4) . ?
C11 C12 1.517(4) . ?
C11 H11 0.9800 . ?
C12 C21 1.379(4) . ?
C12 C13 1.406(4) . ?
C13 C14 1.358(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.414(5) . ?
C14 H14 0.9300 . ?
C15 C20 1.414(5) . ?
C15 C16 1.421(5) . ?
C16 C17 1.348(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.405(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.416(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.441(4) . ?
C21 C22 1.509(4) . ?
C22 O1 1.235(4) . ?
C22 N3 1.345(4) . ?
C23 N3 1.482(4) . ?
C23 C25 1.515(7) . ?
C23 C24 1.523(5) . ?
C23 H23 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 N3 1.476(5) . ?
C26 C27 1.522(6) . ?
C26 C28 1.523(6) . ?
C26 H26 0.9800 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 N6 1.390(4) . ?
C29 C30 1.391(5) . ?
C29 C34 1.404(5) . ?
C30 C31 1.382(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.377(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.378(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.377(5) . ?
C33 H33 0.9300 . ?
C34 N5 1.412(4) . ?
C35 C36 1.343(5) . ?
C35 N5 1.374(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.418(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.352(5) . ?
C37 H37 0.9300 . ?
C38 N5 1.375(4) . ?
C38 C39 1.497(5) . ?
C39 N6 1.470(4) . ?
C39 C40 1.510(4) . ?
C39 H39 0.9800 . ?
C40 C49 1.374(4) . ?
C40 C41 1.416(5) . ?
C41 C42 1.359(5) . ?
C41 H41 0.9300 . ?
C42 C43 1.399(5) . ?
C42 H42 0.9300 . ?
C43 C48 1.413(5) . ?
C43 C44 1.423(5) . ?
C44 C45 1.352(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.381(7) . ?
C45 H45 0.9300 . ?
C46 C47 1.369(6) . ?
C46 H46 0.9300 . ?
C47 C48 1.417(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.434(4) . ?
C49 C50 1.515(5) . ?
C50 O2 1.222(4) . ?
C50 N4 1.357(4) . ?
C51 N4 1.478(5) . ?
C51 C52 1.529(6) . ?
C51 C53 1.530(6) . ?
C51 H51 0.9800 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 N4 1.490(5) . ?
C54 C55 1.520(6) . ?
C54 C56 1.528(5) . ?
C54 H54 0.9800 . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
N1 H1 0.8600 . ?
N6 H6 0.8600 . ?
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
C6 C1 C2 C3 1.5(5) . . . . ?
N1 C1 C2 C3 -174.2(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 -0.9(7) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C4 C5 C6 N2 178.9(3) . . . . ?
N1 C1 C6 C5 174.4(3) . . . . ?
C2 C1 C6 C5 -1.2(5) . . . . ?
N1 C1 C6 N2 -4.6(5) . . . . ?
C2 C1 C6 N2 179.7(3) . . . . ?
N2 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 N2 0.5(4) . . . . ?
C8 C9 C10 C11 -174.2(4) . . . . ?
C9 C10 C11 N1 -162.1(4) . . . . ?
N2 C10 C11 N1 23.9(4) . . . . ?
C9 C10 C11 C12 -40.8(5) . . . . ?
N2 C10 C11 C12 145.2(3) . . . . ?
N1 C11 C12 C21 -136.1(3) . . . . ?
C10 C11 C12 C21 103.4(3) . . . . ?
N1 C11 C12 C13 48.4(4) . . . . ?
C10 C11 C12 C13 -72.1(4) . . . . ?
C21 C12 C13 C14 0.8(5) . . . . ?
C11 C12 C13 C14 176.3(3) . . . . ?
C12 C13 C14 C15 -1.1(5) . . . . ?
C13 C14 C15 C20 1.3(5) . . . . ?
C13 C14 C15 C16 -178.4(3) . . . . ?
C14 C15 C16 C17 178.9(4) . . . . ?
C20 C15 C16 C17 -0.8(6) . . . . ?
C15 C16 C17 C18 0.8(7) . . . . ?
C16 C17 C18 C19 -0.4(7) . . . . ?
C17 C18 C19 C20 0.1(7) . . . . ?
C14 C15 C20 C19 -179.3(3) . . . . ?
C16 C15 C20 C19 0.4(5) . . . . ?
C14 C15 C20 C21 -1.2(4) . . . . ?
C16 C15 C20 C21 178.5(3) . . . . ?
C18 C19 C20 C15 -0.1(5) . . . . ?
C18 C19 C20 C21 -178.1(4) . . . . ?
C13 C12 C21 C20 -0.6(4) . . . . ?
C11 C12 C21 C20 -176.2(3) . . . . ?
C13 C12 C21 C22 170.1(3) . . . . ?
C11 C12 C21 C22 -5.4(4) . . . . ?
C15 C20 C21 C12 0.9(4) . . . . ?
C19 C20 C21 C12 178.9(3) . . . . ?
C15 C20 C21 C22 -170.1(3) . . . . ?
C19 C20 C21 C22 8.0(4) . . . . ?
C12 C21 C22 O1 -87.3(3) . . . . ?
C20 C21 C22 O1 83.5(4) . . . . ?
C12 C21 C22 N3 92.7(4) . . . . ?
C20 C21 C22 N3 -96.4(3) . . . . ?
N6 C29 C30 C31 -176.1(3) . . . . ?
C34 C29 C30 C31 1.3(5) . . . . ?
C29 C30 C31 C32 -0.3(6) . . . . ?
C30 C31 C32 C33 -1.3(7) . . . . ?
C31 C32 C33 C34 1.8(6) . . . . ?
C32 C33 C34 C29 -0.7(6) . . . . ?
C32 C33 C34 N5 178.9(3) . . . . ?
N6 C29 C34 C33 176.7(3) . . . . ?
C30 C29 C34 C33 -0.8(5) . . . . ?
N6 C29 C34 N5 -2.9(4) . . . . ?
C30 C29 C34 N5 179.5(3) . . . . ?
N5 C35 C36 C37 0.4(4) . . . . ?
C35 C36 C37 C38 -0.3(4) . . . . ?
C36 C37 C38 N5 0.1(4) . . . . ?
C36 C37 C38 C39 -175.2(4) . . . . ?
C37 C38 C39 N6 -149.8(4) . . . . ?
N5 C38 C39 N6 35.3(4) . . . . ?
C37 C38 C39 C40 -27.6(5) . . . . ?
N5 C38 C39 C40 157.5(3) . . . . ?
N6 C39 C40 C49 -121.3(3) . . . . ?
C38 C39 C40 C49 118.9(3) . . . . ?
N6 C39 C40 C41 58.9(4) . . . . ?
C38 C39 C40 C41 -61.0(4) . . . . ?
C49 C40 C41 C42 -0.2(5) . . . . ?
C39 C40 C41 C42 179.6(3) . . . . ?
C40 C41 C42 C43 1.2(6) . . . . ?
C41 C42 C43 C48 -1.1(5) . . . . ?
C41 C42 C43 C44 180.0(4) . . . . ?
C42 C43 C44 C45 -179.3(4) . . . . ?
C48 C43 C44 C45 1.8(6) . . . . ?
C43 C44 C45 C46 0.4(7) . . . . ?
C44 C45 C46 C47 -1.3(8) . . . . ?
C45 C46 C47 C48 0.0(7) . . . . ?
C42 C43 C48 C47 178.0(3) . . . . ?
C44 C43 C48 C47 -3.0(5) . . . . ?
C42 C43 C48 C49 0.0(5) . . . . ?
C44 C43 C48 C49 178.9(3) . . . . ?
C46 C47 C48 C43 2.2(6) . . . . ?
C46 C47 C48 C49 -179.8(4) . . . . ?
C41 C40 C49 C48 -1.0(5) . . . . ?
C39 C40 C49 C48 179.2(3) . . . . ?
C41 C40 C49 C50 172.5(3) . . . . ?
C39 C40 C49 C50 -7.4(5) . . . . ?
C43 C48 C49 C40 1.1(5) . . . . ?
C47 C48 C49 C40 -176.9(3) . . . . ?
C43 C48 C49 C50 -172.6(3) . . . . ?
C47 C48 C49 C50 9.4(5) . . . . ?
C40 C49 C50 O2 -94.6(4) . . . . ?
C48 C49 C50 O2 78.9(4) . . . . ?
C40 C49 C50 N4 84.7(4) . . . . ?
C48 C49 C50 N4 -101.8(3) . . . . ?
C6 C1 N1 C11 28.7(5) . . . . ?
C2 C1 N1 C11 -155.7(3) . . . . ?
C10 C11 N1 C1 -36.5(4) . . . . ?
C12 C11 N1 C1 -158.3(3) . . . . ?
C8 C7 N2 C10 0.1(4) . . . . ?
C8 C7 N2 C6 178.8(3) . . . . ?
C9 C10 N2 C7 -0.4(4) . . . . ?
C11 C10 N2 C7 175.0(3) . . . . ?
C9 C10 N2 C6 -179.1(3) . . . . ?
C11 C10 N2 C6 -3.8(5) . . . . ?
C5 C6 N2 C7 -5.0(5) . . . . ?
C1 C6 N2 C7 174.1(3) . . . . ?
C5 C6 N2 C10 173.6(3) . . . . ?
C1 C6 N2 C10 -7.4(5) . . . . ?
O1 C22 N3 C26 -176.4(3) . . . . ?
C21 C22 N3 C26 3.5(5) . . . . ?
O1 C22 N3 C23 1.9(5) . . . . ?
C21 C22 N3 C23 -178.2(3) . . . . ?
C27 C26 N3 C22 -117.4(4) . . . . ?
C28 C26 N3 C22 115.6(4) . . . . ?
C27 C26 N3 C23 64.3(4) . . . . ?
C28 C26 N3 C23 -62.7(4) . . . . ?
C25 C23 N3 C22 62.8(4) . . . . ?
C24 C23 N3 C22 -64.2(5) . . . . ?
C25 C23 N3 C26 -118.9(4) . . . . ?
C24 C23 N3 C26 114.2(4) . . . . ?
O2 C50 N4 C51 -172.3(4) . . . . ?
C49 C50 N4 C51 8.4(5) . . . . ?
O2 C50 N4 C54 4.4(5) . . . . ?
C49 C50 N4 C54 -174.9(3) . . . . ?
C52 C51 N4 C50 -125.2(4) . . . . ?
C53 C51 N4 C50 109.1(4) . . . . ?
C52 C51 N4 C54 58.0(5) . . . . ?
C53 C51 N4 C54 -67.7(5) . . . . ?
C55 C54 N4 C50 62.0(5) . . . . ?
C56 C54 N4 C50 -66.4(4) . . . . ?
C55 C54 N4 C51 -121.2(4) . . . . ?
C56 C54 N4 C51 110.4(4) . . . . ?
C36 C35 N5 C38 -0.4(4) . . . . ?
C36 C35 N5 C34 178.0(3) . . . . ?
C37 C38 N5 C35 0.2(4) . . . . ?
C39 C38 N5 C35 176.3(3) . . . . ?
C37 C38 N5 C34 -178.3(3) . . . . ?
C39 C38 N5 C34 -2.2(4) . . . . ?
C33 C34 N5 C35 -14.0(5) . . . . ?
C29 C34 N5 C35 165.7(3) . . . . ?
C33 C34 N5 C38 164.2(3) . . . . ?
C29 C34 N5 C38 -16.1(4) . . . . ?
C30 C29 N6 C39 -142.7(3) . . . . ?
C34 C29 N6 C39 39.8(4) . . . . ?
C38 C39 N6 C29 -54.0(4) . . . . ?
C40 C39 N6 C29 -177.0(3) . . . . ?
