#------------------------------------------------------------------------------
#$Date: 2023-10-06 02:53:15 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286719 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/96/1569694.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_1569694
loop_
_publ_author_name
'Hao, Yu'
'Li, Zi-Hao'
'Ma, Zhi-Gang'
'Liu, Ru-Xin'
'Ge, Rui-Tian'
'Li, Quan-Zhe'
'Ding, Tong-Mei'
'Zhang, Shu-Yu'
_publ_section_title
;
 Axially chiral styrene-based organocatalysts and their application in
 asymmetric cascade Michael/cyclization reaction.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              9496
_journal_page_last               9502
_journal_paper_doi               10.1039/d3sc02705h
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H30 N4 O2, C H4 O'
_chemical_formula_sum            'C36 H34 N4 O3'
_chemical_formula_weight         570.67
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-25 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.977(5)
_cell_length_b                   11.977
_cell_length_c                   42.045(13)
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.96
_cell_measurement_theta_min      3.68
_cell_volume                     6031(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            61410
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.142
_diffrn_reflns_theta_max         67.142
_diffrn_reflns_theta_min         3.690
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             2416
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 3382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     794
_refine_ls_number_reflns         10685
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0863P)²+0.1508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                8621
_reflns_number_total             10685
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02705h2.cif
_cod_data_source_block           a_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' 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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569692--1569694.cif.
;
_cod_original_cell_volume        6031(5)
_cod_database_code               1569694
_shelx_shelxl_version_number     2018/3
_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   0.904
_shelx_estimated_absorpt_t_max   0.915
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'
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
N1 N 1.1011(3) 0.3391(3) 0.51404(11) 0.0567(10) Uani 1 1 d . . . . .
H1 H 1.135658 0.400869 0.519670 0.068 Uiso 1 1 calc R U . . .
C1 C 0.9861(4) 0.2880(4) 0.40891(11) 0.0480(10) Uani 1 1 d . . . . .
N2 N 0.7346(3) 0.2916(3) 0.46001(9) 0.0417(8) Uani 1 1 d . . . . .
H2 H 0.741055 0.224048 0.468044 0.050 Uiso 1 1 calc R U . . .
C2 C 1.0860(4) 0.2224(5) 0.40406(14) 0.0657(13) Uani 1 1 d . . . . .
H2A H 1.101313 0.159133 0.416962 0.079 Uiso 1 1 calc R U . . .
N3 N 0.5065(3) 0.2257(3) 0.49224(10) 0.0501(9) Uani 1 1 d . . . . .
H3 H 0.550444 0.167365 0.489993 0.060 Uiso 1 1 calc R U . . .
C3 C 1.1599(6) 0.2549(6) 0.3797(2) 0.093(2) Uani 1 1 d . . . . .
H3A H 1.227594 0.214672 0.376935 0.111 Uiso 1 1 calc R U . . .
O4 O 0.5141(3) 1.0091(3) 0.42973(8) 0.0535(8) Uani 1 1 d . . . . .
N4 N 0.3931(3) 0.0109(3) 0.50230(9) 0.0476(8) Uani 1 1 d . . . . .
C4 C 1.1368(6) 0.3433(9) 0.35972(18) 0.102(3) Uani 1 1 d . . . . .
H4 H 1.187056 0.360154 0.342909 0.123 Uiso 1 1 calc R U . . .
O5 O 0.3220(5) 0.4564(8) 0.60032(16) 0.138(3) Uani 1 1 d D . . . .
H5 H 0.294356 0.481846 0.583455 0.207 Uiso 1 1 calc DR U . . .
N5 N 0.6959(3) 0.7904(3) 0.50398(8) 0.0394(8) Uani 1 1 d . . . . .
H11 H 0.698(5) 0.729(5) 0.4977(14) 0.059 Uiso 1 1 d . U . . .
C5 C 1.0424(5) 0.4079(6) 0.36358(14) 0.0702(15) Uani 1 1 d . . . . .
O6 O 0.2599(4) 0.4993(4) 0.53892(12) 0.0834(13) Uani 1 1 d . . . . .
H6 H 0.319342 0.484155 0.529247 0.125 Uiso 1 1 calc R U . . .
N6 N 0.5426(3) 0.7410(3) 0.44550(9) 0.0457(8) Uani 1 1 d . . . . .
H13 H 0.569(5) 0.679(5) 0.4531(15) 0.069 Uiso 1 1 d . U . . .
C6 C 0.9643(4) 0.3792(4) 0.38891(11) 0.0531(11) Uani 1 1 d . . . . .
N7 N 0.5410(3) 0.4946(3) 0.57178(9) 0.0460(8) Uani 1 1 d . . . . .
H10 H 0.475(4) 0.495(5) 0.5826(14) 0.069 Uiso 1 1 d D U . . .
C7 C 0.8662(4) 0.4414(4) 0.39350(12) 0.0543(11) Uani 1 1 d . . . . .
H7 H 0.851999 0.504111 0.380272 0.065 Uiso 1 1 calc R U . . .
N8 N 0.3997(4) 0.5515(4) 0.42743(11) 0.0614(10) Uani 1 1 d . . . . .
C8 C 0.7908(4) 0.4136(4) 0.41660(11) 0.0466(10) Uani 1 1 d . . . . .
H8 H 0.723573 0.454937 0.418849 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8134(3) 0.3237(3) 0.43695(10) 0.0393(8) Uani 1 1 d . . . . .
H9 H 1.017(6) 0.480(6) 0.3530(19) 0.09(2) Uiso 1 1 d . . . . .
C10 C 0.9106(3) 0.2616(3) 0.43366(11) 0.0425(9) Uani 1 1 d . . . . .
C11 C 0.9401(3) 0.1740(3) 0.45755(11) 0.0429(9) Uani 1 1 d . . . . .
O1 O 0.6686(3) 0.5620(2) 0.46719(8) 0.0496(7) Uani 1 1 d . . . . .
C12 C 1.0443(4) 0.3238(4) 0.48651(12) 0.0503(10) Uani 1 1 d . . . . .
H12 H 1.036209 0.378704 0.470353 0.060 Uiso 1 1 calc R U . . .
C13 C 1.0001(3) 0.2187(3) 0.48517(11) 0.0433(9) Uani 1 1 d . . . . .
C14 C 1.0312(4) 0.1649(4) 0.51482(11) 0.0471(10) Uani 1 1 d . . . . .
C15 C 1.0961(4) 0.2431(4) 0.53172(12) 0.0523(11) Uani 1 1 d . . . . .
C16 C 1.1444(4) 0.2189(5) 0.56084(12) 0.0625(13) Uani 1 1 d . . . . .
H16 H 1.188441 0.272803 0.571686 0.075 Uiso 1 1 calc R U . . .
C17 C 1.1267(5) 0.1150(6) 0.57357(13) 0.0716(15) Uani 1 1 d . . . . .
H17 H 1.160802 0.095594 0.593211 0.086 Uiso 1 1 calc R U . . .
C18 C 1.0602(5) 0.0385(5) 0.55826(13) 0.0701(15) Uani 1 1 d . . . . .
H18 H 1.047343 -0.032003 0.567915 0.084 Uiso 1 1 calc R U . . .
C19 C 1.0118(4) 0.0615(4) 0.52929(13) 0.0585(12) Uani 1 1 d . . . . .
H19 H 0.965676 0.007529 0.519204 0.070 Uiso 1 1 calc R U . . .
C20 C 0.9198(4) 0.0641(4) 0.45425(11) 0.0472(10) Uani 1 1 d . . . . .
H20 H 0.947430 0.019785 0.471264 0.057 Uiso 1 1 calc R U . . .
C21 C 0.8631(4) -0.0003(4) 0.42939(11) 0.0480(10) Uani 1 1 d . . . . .
C22 C 0.8620(4) -0.1168(4) 0.43336(13) 0.0530(11) Uani 1 1 d . . . . .
H22 H 0.897752 -0.148620 0.451380 0.064 Uiso 1 1 calc R U . . .
C23 C 0.8104(4) -0.1857(4) 0.41170(14) 0.0609(13) Uani 1 1 d . . . . .
H23 H 0.810458 -0.264248 0.414887 0.073 Uiso 1 1 calc R U . . .
C24 C 0.7593(5) -0.1416(5) 0.38581(14) 0.0679(15) Uani 1 1 d . . . . .
H24 H 0.725627 -0.189336 0.370519 0.081 Uiso 1 1 calc R U . . .
C25 C 0.7562(6) -0.0278(5) 0.38168(14) 0.0764(17) Uani 1 1 d . . . . .
H25 H 0.717635 0.003021 0.363998 0.092 Uiso 1 1 calc R U . . .
O2 O 0.4381(3) 0.4911(3) 0.50138(8) 0.0531(8) Uani 1 1 d . . . . .
C26 C 0.8091(5) 0.0422(4) 0.40315(14) 0.0660(14) Uani 1 1 d . . . . .
H26 H 0.807989 0.120582 0.399726 0.079 Uiso 1 1 calc R U . . .
C27 C 0.6497(3) 0.3554(3) 0.47093(10) 0.0375(8) Uani 1 1 d . . . . .
C28 C 0.5490(3) 0.3233(3) 0.48548(10) 0.0400(9) Uani 1 1 d . . . . .
C29 C 0.5165(4) 0.4407(3) 0.48960(10) 0.0420(9) Uani 1 1 d . . . . .
C30 C 0.6228(3) 0.4730(3) 0.47415(11) 0.0419(9) Uani 1 1 d . . . . .
C31 C 0.3962(4) 0.1028(4) 0.52498(13) 0.0556(11) Uani 1 1 d . . . . .
H31A H 0.465329 0.101049 0.537873 0.067 Uiso 1 1 calc R U . . .
H31B H 0.330641 0.101166 0.539317 0.067 Uiso 1 1 calc R U . . .
C32 C 0.3934(4) 0.2047(4) 0.50313(13) 0.0526(11) Uani 1 1 d . . . . .
H32 H 0.361810 0.271266 0.514307 0.063 Uiso 1 1 calc R U . . .
C33 C 0.3170(4) 0.1665(4) 0.47591(15) 0.0616(13) Uani 1 1 d . . . . .
H33A H 0.244134 0.205370 0.476908 0.074 Uiso 1 1 calc R U . . .
H33B H 0.351948 0.181973 0.455024 0.074 Uiso 1 1 calc R U . . .
C34 C 0.3022(4) 0.0413(4) 0.48085(14) 0.0576(12) Uani 1 1 d . . . . .
H34A H 0.228767 0.024715 0.490561 0.069 Uiso 1 1 calc R U . . .
H34B H 0.308357 0.000644 0.460426 0.069 Uiso 1 1 calc R U . . .
C35 C 0.3792(5) -0.0974(4) 0.51716(14) 0.0605(12) Uani 1 1 d . . . . .
H35A H 0.376280 -0.155338 0.500710 0.091 Uiso 1 1 calc R U . . .
H35B H 0.309506 -0.098262 0.529391 0.091 Uiso 1 1 calc R U . . .
H35C H 0.442235 -0.111936 0.531417 0.091 Uiso 1 1 calc R U . . .
C36 C 0.8410(3) 0.7519(3) 0.58063(10) 0.0421(9) Uani 1 1 d . . . . .
C37 C 0.8991(4) 0.6668(4) 0.59794(12) 0.0508(11) Uani 1 1 d . . . . .
H37 H 0.903077 0.592891 0.589811 0.061 Uiso 1 1 calc R U . . .
C38 C 0.9490(5) 0.6931(5) 0.62649(14) 0.0671(14) Uani 1 1 d . . . . .
H38 H 0.992302 0.638207 0.637168 0.080 Uiso 1 1 calc R U . . .
C39 C 0.9373(5) 0.7985(5) 0.63996(13) 0.0618(13) Uani 1 1 d . . . . .
H39 H 0.965510 0.812399 0.660705 0.074 Uiso 1 1 calc R U . . .
C40 C 0.8852(5) 0.8826(4) 0.62350(11) 0.0565(12) Uani 1 1 d . . . . .
H40 H 0.882744 0.955966 0.632063 0.068 Uiso 1 1 calc R U . . .
C41 C 0.8348(4) 0.8596(4) 0.59361(11) 0.0464(10) Uani 1 1 d . . . . .
C42 C 0.7811(4) 0.9436(4) 0.57585(12) 0.0517(11) Uani 1 1 d . . . . .
H42 H 0.776109 1.016783 0.584433 0.062 Uiso 1 1 calc R U . . .
C43 C 0.7361(4) 0.9227(3) 0.54674(11) 0.0470(10) Uani 1 1 d . . . . .
H43 H 0.699905 0.980815 0.535337 0.056 Uiso 1 1 calc R U . . .
C44 C 0.7432(3) 0.8150(3) 0.53355(10) 0.0390(8) Uani 1 1 d . . . . .
C45 C 0.7945(3) 0.7300(3) 0.55008(10) 0.0388(9) Uani 1 1 d . . . . .
C46 C 0.7944(3) 0.6143(3) 0.53724(10) 0.0402(9) Uani 1 1 d . . . . .
C47 C 0.8635(3) 0.5798(3) 0.51422(11) 0.0439(9) Uani 1 1 d . . . . .
H47 H 0.856156 0.503944 0.508007 0.053 Uiso 1 1 calc R U . . .
C48 C 0.9498(4) 0.6448(3) 0.49726(11) 0.0456(10) Uani 1 1 d . . . . .
C49 C 1.0064(4) 0.7357(4) 0.51042(14) 0.0559(12) Uani 1 1 d . . . . .
H49 H 0.991502 0.757662 0.531714 0.067 Uiso 1 1 calc R U . . .
C50 C 1.0840(4) 0.7937(4) 0.49259(16) 0.0649(14) Uani 1 1 d . . . . .
H50 H 1.120328 0.856756 0.501564 0.078 Uiso 1 1 calc R U . . .
C51 C 1.1091(4) 0.7620(4) 0.46250(16) 0.0684(15) Uani 1 1 d . . . . .
H51 H 1.163467 0.801856 0.450611 0.082 Uiso 1 1 calc R U . . .
C52 C 1.0554(5) 0.6717(5) 0.44923(15) 0.0647(14) Uani 1 1 d . . . . .
H52 H 1.072913 0.649125 0.428149 0.078 Uiso 1 1 calc R U . . .
C53 C 0.9755(4) 0.6134(4) 0.46666(13) 0.0527(11) Uani 1 1 d . . . . .
H53 H 0.938387 0.551417 0.457324 0.063 Uiso 1 1 calc R U . . .
C54 C 0.6067(4) 0.5810(4) 0.56233(11) 0.0454(10) Uani 1 1 d . . . . .
H54 H 0.586387 0.657523 0.563782 0.054 Uiso 1 1 calc R U . . .
C55 C 0.7058(3) 0.5431(3) 0.55049(10) 0.0393(9) Uani 1 1 d . . . . .
C56 C 0.7021(3) 0.4239(3) 0.55318(10) 0.0395(8) Uani 1 1 d . . . . .
C57 C 0.5981(4) 0.3967(3) 0.56639(11) 0.0439(9) Uani 1 1 d . . . . .
C58 C 0.5674(4) 0.2879(4) 0.57368(11) 0.0476(10) Uani 1 1 d . . . . .
H58 H 0.497034 0.271624 0.583025 0.057 Uiso 1 1 calc R U . . .
C59 C 0.6424(4) 0.2051(4) 0.56689(13) 0.0548(11) Uani 1 1 d . . . . .
H59 H 0.623571 0.129929 0.571668 0.066 Uiso 1 1 calc R U . . .
C60 C 0.7460(4) 0.2285(4) 0.55309(12) 0.0504(11) Uani 1 1 d . . . . .
H60 H 0.795489 0.168938 0.548283 0.061 Uiso 1 1 calc R U . . .
C61 C 0.7772(4) 0.3360(3) 0.54640(10) 0.0435(9) Uani 1 1 d . . . . .
H61 H 0.848236 0.351262 0.537330 0.052 Uiso 1 1 calc R U . . .
C62 C 0.6472(3) 0.8612(3) 0.48309(10) 0.0367(8) Uani 1 1 d . . . . .
C63 C 0.5789(3) 0.8348(3) 0.45704(9) 0.0379(8) Uani 1 1 d . . . . .
C64 C 0.5653(3) 0.9546(3) 0.44933(10) 0.0414(9) Uani 1 1 d . . . . .
C65 C 0.6410(3) 0.9802(3) 0.47632(10) 0.0393(9) Uani 1 1 d . . . . .
C66 C 0.4454(5) 0.5489(4) 0.39567(14) 0.0660(14) Uani 1 1 d . . . . .
H66A H 0.385212 0.543600 0.379602 0.079 Uiso 1 1 calc R U . . .
H66B H 0.496584 0.484614 0.393002 0.079 Uiso 1 1 calc R U . . .
C67 C 0.5084(5) 0.6589(4) 0.39254(12) 0.0551(11) Uani 1 1 d . . . . .
H67A H 0.493606 0.694163 0.371656 0.066 Uiso 1 1 calc R U . . .
H67B H 0.589779 0.647307 0.394892 0.066 Uiso 1 1 calc R U . . .
C68 C 0.4628(4) 0.7309(4) 0.41962(12) 0.0525(11) Uani 1 1 d . . . . .
H68 H 0.439960 0.806159 0.411638 0.063 Uiso 1 1 calc R U . . .
C69 C 0.3629(4) 0.6653(5) 0.43059(14) 0.0624(13) Uani 1 1 d . . . . .
H69A H 0.343899 0.683124 0.452941 0.075 Uiso 1 1 calc R U . . .
H69B H 0.297095 0.680261 0.416973 0.075 Uiso 1 1 calc R U . . .
C70 C 0.3113(6) 0.4693(7) 0.43269(19) 0.095(2) Uani 1 1 d . . . . .
H70A H 0.286510 0.472953 0.454884 0.143 Uiso 1 1 calc R U . . .
H70B H 0.339932 0.394372 0.428123 0.143 Uiso 1 1 calc R U . . .
H70C H 0.248176 0.485573 0.418599 0.143 Uiso 1 1 calc R U . . .
C71 C 0.2387(8) 0.4655(11) 0.6265(3) 0.137(4) Uani 1 1 d D . . . .
H71A H 0.234311 0.543274 0.633712 0.206 Uiso 1 1 calc R U . . .
H71B H 0.261738 0.417926 0.644334 0.206 Uiso 1 1 calc R U . . .
H71C H 0.165370 0.441427 0.618831 0.206 Uiso 1 1 calc R U . . .
C72 C 0.2443(9) 0.6110(8) 0.5391(3) 0.147(5) Uani 1 1 d . . . . .
H72A H 0.314697 0.648208 0.544495 0.221 Uiso 1 1 calc R U . . .
H72B H 0.187485 0.630270 0.554962 0.221 Uiso 1 1 calc R U . . .
H72C H 0.219478 0.635523 0.518037 0.221 Uiso 1 1 calc R U . . .
O3 O 0.6792(2) 1.0673(2) 0.48754(7) 0.0439(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 0.0181 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
C12 N1 C15 109.1(4) . . ?
C6 C1 C10 119.7(4) . . ?
C6 C1 C2 119.6(5) . . ?
C10 C1 C2 120.7(5) . . ?
C27 N2 C9 125.7(3) . . ?
C3 C2 C1 118.2(6) . . ?
C28 N3 C32 126.0(4) . . ?
C4 C3 C2 121.9(6) . . ?
C35 N4 C31 113.4(4) . . ?
C35 N4 C34 113.8(4) . . ?
C31 N4 C34 103.6(4) . . ?
C3 C4 C5 121.5(6) . . ?
C62 N5 C44 128.3(3) . . ?
C4 C5 C6 118.7(6) . . ?
C63 N6 C68 124.9(4) . . ?
C1 C6 C7 119.2(4) . . ?
C1 C6 C5 120.1(5) . . ?
C7 C6 C5 120.8(5) . . ?
C54 N7 C57 108.2(4) . . ?
C8 C7 C6 121.4(4) . . ?
C69 N8 C66 102.9(4) . . ?
C69 N8 C70 113.7(5) . . ?
C66 N8 C70 113.5(5) . . ?
C7 C8 C9 119.5(4) . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 N2 119.1(4) . . ?
C8 C9 N2 120.1(4) . . ?
C9 C10 C1 119.3(4) . . ?
C9 C10 C11 120.4(4) . . ?
C1 C10 C11 120.0(4) . . ?
C20 C11 C13 121.8(4) . . ?
C20 C11 C10 125.1(4) . . ?
C13 C11 C10 113.0(3) . . ?
N1 C12 C13 110.7(4) . . ?
C12 C13 C14 105.9(4) . . ?
C12 C13 C11 124.0(4) . . ?
C14 C13 C11 130.0(4) . . ?
C19 C14 C15 117.4(4) . . ?
C19 C14 C13 136.4(4) . . ?
C15 C14 C13 106.2(4) . . ?
N1 C15 C16 129.5(5) . . ?
N1 C15 C14 107.9(4) . . ?
C16 C15 C14 122.5(5) . . ?
C17 C16 C15 118.0(5) . . ?
C18 C17 C16 120.8(5) . . ?
C17 C18 C19 121.7(6) . . ?
C18 C19 C14 119.4(5) . . ?
C11 C20 C21 132.2(4) . . ?
C26 C21 C22 117.2(4) . . ?
C26 C21 C20 126.5(4) . . ?
C22 C21 C20 116.2(4) . . ?
C23 C22 C21 121.4(5) . . ?
C24 C23 C22 120.0(5) . . ?
C23 C24 C25 120.0(5) . . ?
C24 C25 C26 120.4(6) . . ?
C21 C26 C25 120.9(5) . . ?
N2 C27 C28 129.6(4) . . ?
N2 C27 C30 138.4(4) . . ?
C28 C27 C30 92.0(3) . . ?
N3 C28 C27 132.4(4) . . ?
N3 C28 C29 136.7(4) . . ?
C27 C28 C29 90.9(3) . . ?
O2 C29 C28 136.4(4) . . ?
O2 C29 C30 135.2(4) . . ?
C28 C29 C30 88.4(3) . . ?
O1 C30 C27 135.9(4) . . ?
O1 C30 C29 135.4(4) . . ?
C27 C30 C29 88.7(3) . . ?
N4 C31 C32 102.1(4) . . ?
N3 C32 C31 107.9(4) . . ?
N3 C32 C33 111.9(4) . . ?
C31 C32 C33 102.9(4) . . ?
C34 C33 C32 105.1(4) . . ?
N4 C34 C33 104.1(4) . . ?
C41 C36 C45 120.0(4) . . ?
C41 C36 C37 118.9(4) . . ?
C45 C36 C37 121.1(4) . . ?
C38 C37 C36 119.4(5) . . ?
C37 C38 C39 121.2(5) . . ?
C40 C39 C38 120.4(5) . . ?
C39 C40 C41 119.8(5) . . ?
C36 C41 C42 118.4(4) . . ?
C36 C41 C40 120.0(4) . . ?
C42 C41 C40 121.6(4) . . ?
C43 C42 C41 121.8(4) . . ?
C42 C43 C44 120.0(4) . . ?
C45 C44 N5 118.3(4) . . ?
C45 C44 C43 120.4(4) . . ?
N5 C44 C43 121.3(4) . . ?
C44 C45 C36 119.6(4) . . ?
C44 C45 C46 120.3(4) . . ?
C36 C45 C46 120.0(4) . . ?
C47 C46 C55 122.8(4) . . ?
C47 C46 C45 123.3(4) . . ?
C55 C46 C45 113.8(3) . . ?
C46 C47 C48 128.3(4) . . ?
C53 C48 C49 118.4(4) . . ?
C53 C48 C47 117.6(4) . . ?
C49 C48 C47 124.0(4) . . ?
C50 C49 C48 120.2(5) . . ?
C51 C50 C49 121.0(5) . . ?
C50 C51 C52 119.7(5) . . ?
C51 C52 C53 120.1(5) . . ?
C48 C53 C52 120.6(5) . . ?
N7 C54 C55 110.9(4) . . ?
C54 C55 C56 106.0(4) . . ?
C54 C55 C46 124.9(4) . . ?
C56 C55 C46 129.1(4) . . ?
C57 C56 C61 118.1(4) . . ?
C57 C56 C55 106.9(4) . . ?
C61 C56 C55 135.0(4) . . ?
N7 C57 C58 129.2(4) . . ?
N7 C57 C56 108.0(4) . . ?
C58 C57 C56 122.8(4) . . ?
C59 C58 C57 117.4(4) . . ?
C58 C59 C60 121.6(4) . . ?
C61 C60 C59 121.1(4) . . ?
C60 C61 C56 119.0(4) . . ?
N5 C62 C63 128.1(4) . . ?
N5 C62 C65 139.7(4) . . ?
C63 C62 C65 92.2(3) . . ?
N6 C63 C62 132.9(4) . . ?
N6 C63 C64 136.1(4) . . ?
C62 C63 C64 91.0(3) . . ?
O4 C64 C63 136.3(4) . . ?
O4 C64 C65 135.6(4) . . ?
C63 C64 C65 88.0(3) . . ?
O3 C65 C62 137.3(4) . . ?
O3 C65 C64 133.9(4) . . ?
C62 C65 C64 88.8(3) . . ?
N8 C66 C67 104.4(4) . . ?
C66 C67 C68 104.3(4) . . ?
N6 C68 C69 109.7(4) . . ?
N6 C68 C67 111.7(4) . . ?
C69 C68 C67 102.6(4) . . ?
N8 C69 C68 102.8(4) . . ?
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
N1 C12 1.355(6) . ?
N1 C15 1.371(7) . ?
C1 C6 1.402(7) . ?
C1 C10 1.415(7) . ?
C1 C2 1.445(7) . ?
N2 C27 1.353(5) . ?
N2 C9 1.407(5) . ?
C2 C3 1.409(9) . ?
N3 C28 1.306(5) . ?
N3 C32 1.452(6) . ?
C3 C4 1.380(11) . ?
O4 C64 1.217(5) . ?
N4 C35 1.450(6) . ?
N4 C31 1.456(6) . ?
N4 C34 1.460(6) . ?
C4 C5 1.379(10) . ?
O5 C71 1.491(11) . ?
N5 C62 1.353(5) . ?
N5 C44 1.398(6) . ?
C5 C6 1.459(7) . ?
O6 C72 1.351(10) . ?
N6 C63 1.299(5) . ?
N6 C68 1.453(6) . ?
C6 C7 1.404(7) . ?
N7 C54 1.359(6) . ?
N7 C57 1.377(6) . ?
C7 C8 1.368(7) . ?
N8 C69 1.439(7) . ?
N8 C66 1.444(7) . ?
N8 C70 1.463(7) . ?
C8 C9 1.402(6) . ?
C9 C10 1.388(6) . ?
C10 C11 1.495(6) . ?
C11 C20 1.347(6) . ?
C11 C13 1.467(6) . ?
O1 C30 1.234(5) . ?
C12 C13 1.366(6) . ?
C13 C14 1.452(7) . ?
C14 C19 1.399(7) . ?
C14 C15 1.409(7) . ?
C15 C16 1.385(8) . ?
C16 C17 1.372(9) . ?
C17 C18 1.373(9) . ?
C18 C19 1.377(8) . ?
C20 C21 1.465(7) . ?
C21 C26 1.377(8) . ?
C21 C22 1.405(6) . ?
C22 C23 1.377(7) . ?
C23 C24 1.356(9) . ?
C24 C25 1.374(9) . ?
C25 C26 1.385(8) . ?
O2 C29 1.222(5) . ?
C27 C28 1.405(6) . ?
C27 C30 1.451(5) . ?
C28 C29 1.469(6) . ?
C29 C30 1.480(6) . ?
C31 C32 1.528(7) . ?
C32 C33 1.535(8) . ?
C33 C34 1.524(7) . ?
C36 C41 1.402(6) . ?
C36 C45 1.425(6) . ?
C36 C37 1.433(6) . ?
C37 C38 1.377(8) . ?
C38 C39 1.391(8) . ?
C39 C40 1.372(7) . ?
C40 C41 1.421(7) . ?
C41 C42 1.408(6) . ?
C42 C43 1.360(7) . ?
C43 C44 1.407(6) . ?
C44 C45 1.377(6) . ?
C45 C46 1.487(6) . ?
C46 C47 1.339(6) . ?
C46 C55 1.471(6) . ?
C47 C48 1.477(6) . ?
C48 C53 1.375(7) . ?
C48 C49 1.396(7) . ?
C49 C50 1.382(7) . ?
C50 C51 1.355(9) . ?
C51 C52 1.375(9) . ?
C52 C53 1.394(7) . ?
C54 C55 1.365(6) . ?
C55 C56 1.432(6) . ?
C56 C57 1.403(6) . ?
C56 C61 1.413(6) . ?
C57 C58 1.388(6) . ?
C58 C59 1.368(7) . ?
C59 C60 1.398(7) . ?
C60 C61 1.370(6) . ?
C62 C63 1.403(6) . ?
C62 C65 1.456(5) . ?
C63 C64 1.480(5) . ?
C64 C65 1.484(6) . ?
C65 O3 1.233(5) . ?
C66 C67 1.524(7) . ?
C67 C68 1.528(7) . ?
C68 C69 1.504(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
C6 C1 C2 C3 1.7(8) . . . . ?
C10 C1 C2 C3 -178.0(5) . . . . ?
C1 C2 C3 C4 -3.1(11) . . . . ?
C2 C3 C4 C5 3.1(13) . . . . ?
C3 C4 C5 C6 -1.8(12) . . . . ?
C10 C1 C6 C7 -1.3(7) . . . . ?
C2 C1 C6 C7 179.0(5) . . . . ?
C10 C1 C6 C5 179.2(5) . . . . ?
C2 C1 C6 C5 -0.5(7) . . . . ?
C4 C5 C6 C1 0.5(9) . . . . ?
C4 C5 C6 C7 -179.1(6) . . . . ?
C1 C6 C7 C8 -1.3(7) . . . . ?
C5 C6 C7 C8 178.2(5) . . . . ?
C6 C7 C8 C9 2.4(7) . . . . ?
C7 C8 C9 C10 -0.8(7) . . . . ?
C7 C8 C9 N2 -177.6(4) . . . . ?
C27 N2 C9 C10 164.4(4) . . . . ?
C27 N2 C9 C8 -18.8(6) . . . . ?
C8 C9 C10 C1 -1.7(6) . . . . ?
N2 C9 C10 C1 175.1(4) . . . . ?
C8 C9 C10 C11 173.3(4) . . . . ?
N2 C9 C10 C11 -9.9(6) . . . . ?
C6 C1 C10 C9 2.7(6) . . . . ?
C2 C1 C10 C9 -177.6(4) . . . . ?
C6 C1 C10 C11 -172.3(4) . . . . ?
C2 C1 C10 C11 7.4(6) . . . . ?
C9 C10 C11 C20 97.4(5) . . . . ?
C1 C10 C11 C20 -87.6(6) . . . . ?
C9 C10 C11 C13 -85.6(5) . . . . ?
C1 C10 C11 C13 89.4(5) . . . . ?
C15 N1 C12 C13 0.2(5) . . . . ?
N1 C12 C13 C14 0.9(5) . . . . ?
N1 C12 C13 C11 -176.0(4) . . . . ?
C20 C11 C13 C12 165.0(4) . . . . ?
C10 C11 C13 C12 -12.1(6) . . . . ?
C20 C11 C13 C14 -11.1(7) . . . . ?
C10 C11 C13 C14 171.7(4) . . . . ?
C12 C13 C14 C19 177.7(5) . . . . ?
C11 C13 C14 C19 -5.7(8) . . . . ?
C12 C13 C14 C15 -1.7(5) . . . . ?
C11 C13 C14 C15 174.9(4) . . . . ?
C12 N1 C15 C16 177.9(5) . . . . ?
C12 N1 C15 C14 -1.3(5) . . . . ?
C19 C14 C15 N1 -177.7(4) . . . . ?
C13 C14 C15 N1 1.9(5) . . . . ?
C19 C14 C15 C16 3.1(7) . . . . ?
C13 C14 C15 C16 -177.4(4) . . . . ?
N1 C15 C16 C17 -179.7(5) . . . . ?
C14 C15 C16 C17 -0.6(7) . . . . ?
C15 C16 C17 C18 -1.9(8) . . . . ?
C16 C17 C18 C19 2.0(9) . . . . ?
C17 C18 C19 C14 0.5(8) . . . . ?
C15 C14 C19 C18 -2.9(7) . . . . ?
C13 C14 C19 C18 177.7(5) . . . . ?
C13 C11 C20 C21 -179.8(4) . . . . ?
C10 C11 C20 C21 -3.0(8) . . . . ?
C11 C20 C21 C26 -4.4(9) . . . . ?
C11 C20 C21 C22 177.2(5) . . . . ?
C26 C21 C22 C23 0.8(7) . . . . ?
C20 C21 C22 C23 179.4(4) . . . . ?
C21 C22 C23 C24 0.2(8) . . . . ?
C22 C23 C24 C25 -2.0(9) . . . . ?
C23 C24 C25 C26 2.7(10) . . . . ?
C22 C21 C26 C25 -0.1(8) . . . . ?
C20 C21 C26 C25 -178.4(5) . . . . ?
C24 C25 C26 C21 -1.6(10) . . . . ?
C9 N2 C27 C28 157.5(4) . . . . ?
C9 N2 C27 C30 -25.1(8) . . . . ?
C32 N3 C28 C27 -170.1(5) . . . . ?
C32 N3 C28 C29 10.6(9) . . . . ?
N2 C27 C28 N3 -1.4(8) . . . . ?
C30 C27 C28 N3 -179.6(5) . . . . ?
N2 C27 C28 C29 178.1(4) . . . . ?
C30 C27 C28 C29 -0.2(3) . . . . ?
N3 C28 C29 O2 1.5(10) . . . . ?
C27 C28 C29 O2 -178.0(5) . . . . ?
N3 C28 C29 C30 179.6(6) . . . . ?
C27 C28 C29 C30 0.1(3) . . . . ?
N2 C27 C30 O1 1.9(9) . . . . ?
C28 C27 C30 O1 179.8(5) . . . . ?
N2 C27 C30 C29 -177.8(5) . . . . ?
C28 C27 C30 C29 0.2(3) . . . . ?
O2 C29 C30 O1 -1.7(9) . . . . ?
C28 C29 C30 O1 -179.8(5) . . . . ?
O2 C29 C30 C27 178.0(5) . . . . ?
C28 C29 C30 C27 -0.1(3) . . . . ?
C35 N4 C31 C32 -171.8(4) . . . . ?
C34 N4 C31 C32 -48.0(4) . . . . ?
C28 N3 C32 C31 -148.5(5) . . . . ?
C28 N3 C32 C33 99.0(5) . . . . ?
N4 C31 C32 N3 -82.8(5) . . . . ?
N4 C31 C32 C33 35.6(5) . . . . ?
N3 C32 C33 C34 104.6(4) . . . . ?
C31 C32 C33 C34 -11.1(5) . . . . ?
C35 N4 C34 C33 164.3(4) . . . . ?
C31 N4 C34 C33 40.8(5) . . . . ?
C32 C33 C34 N4 -17.3(5) . . . . ?
C41 C36 C37 C38 -1.2(7) . . . . ?
C45 C36 C37 C38 175.9(4) . . . . ?
C36 C37 C38 C39 4.8(8) . . . . ?
C37 C38 C39 C40 -6.8(9) . . . . ?
C38 C39 C40 C41 5.2(8) . . . . ?
C45 C36 C41 C42 0.6(6) . . . . ?
C37 C36 C41 C42 177.7(4) . . . . ?
C45 C36 C41 C40 -177.5(4) . . . . ?
C37 C36 C41 C40 -0.3(7) . . . . ?
C39 C40 C41 C36 -1.7(7) . . . . ?
C39 C40 C41 C42 -179.6(5) . . . . ?
C36 C41 C42 C43 -0.2(7) . . . . ?
C40 C41 C42 C43 177.7(5) . . . . ?
C41 C42 C43 C44 -0.4(7) . . . . ?
C62 N5 C44 C45 -176.1(4) . . . . ?
C62 N5 C44 C43 5.9(7) . . . . ?
C42 C43 C44 C45 0.7(7) . . . . ?
C42 C43 C44 N5 178.7(4) . . . . ?
N5 C44 C45 C36 -178.4(4) . . . . ?
C43 C44 C45 C36 -0.4(6) . . . . ?
N5 C44 C45 C46 -2.7(6) . . . . ?
C43 C44 C45 C46 175.3(4) . . . . ?
C41 C36 C45 C44 -0.2(6) . . . . ?
C37 C36 C45 C44 -177.3(4) . . . . ?
C41 C36 C45 C46 -176.0(4) . . . . ?
C37 C36 C45 C46 6.9(6) . . . . ?
C44 C45 C46 C47 78.9(5) . . . . ?
C36 C45 C46 C47 -105.4(5) . . . . ?
C44 C45 C46 C55 -96.9(5) . . . . ?
C36 C45 C46 C55 78.8(5) . . . . ?
C55 C46 C47 C48 175.1(4) . . . . ?
C45 C46 C47 C48 -0.4(7) . . . . ?
C46 C47 C48 C53 -151.5(5) . . . . ?
C46 C47 C48 C49 28.5(7) . . . . ?
C53 C48 C49 C50 1.7(7) . . . . ?
C47 C48 C49 C50 -178.3(5) . . . . ?
C48 C49 C50 C51 -1.9(8) . . . . ?
C49 C50 C51 C52 1.0(9) . . . . ?
C50 C51 C52 C53 0.1(8) . . . . ?
C49 C48 C53 C52 -0.5(7) . . . . ?
C47 C48 C53 C52 179.5(4) . . . . ?
C51 C52 C53 C48 -0.4(8) . . . . ?
C57 N7 C54 C55 0.6(5) . . . . ?
N7 C54 C55 C56 -0.9(5) . . . . ?
N7 C54 C55 C46 177.9(4) . . . . ?
C47 C46 C55 C54 -149.6(4) . . . . ?
C45 C46 C55 C54 26.3(6) . . . . ?
C47 C46 C55 C56 28.9(7) . . . . ?
C45 C46 C55 C56 -155.3(4) . . . . ?
C54 C55 C56 C57 0.8(5) . . . . ?
C46 C55 C56 C57 -177.9(4) . . . . ?
C54 C55 C56 C61 -177.6(5) . . . . ?
C46 C55 C56 C61 3.7(8) . . . . ?
C54 N7 C57 C58 176.4(5) . . . . ?
C54 N7 C57 C56 -0.1(5) . . . . ?
C61 C56 C57 N7 178.3(4) . . . . ?
C55 C56 C57 N7 -0.5(5) . . . . ?
C61 C56 C57 C58 1.6(6) . . . . ?
C55 C56 C57 C58 -177.2(4) . . . . ?
N7 C57 C58 C59 -177.3(5) . . . . ?
C56 C57 C58 C59 -1.3(7) . . . . ?
C57 C58 C59 C60 -0.1(7) . . . . ?
C58 C59 C60 C61 1.3(8) . . . . ?
C59 C60 C61 C56 -1.0(7) . . . . ?
C57 C56 C61 C60 -0.4(6) . . . . ?
C55 C56 C61 C60 177.9(5) . . . . ?
C44 N5 C62 C63 -164.8(4) . . . . ?
C44 N5 C62 C65 17.1(8) . . . . ?
C68 N6 C63 C62 173.9(5) . . . . ?
C68 N6 C63 C64 -4.6(8) . . . . ?
N5 C62 C63 N6 0.4(8) . . . . ?
C65 C62 C63 N6 179.1(5) . . . . ?
N5 C62 C63 C64 179.3(4) . . . . ?
C65 C62 C63 C64 -1.9(3) . . . . ?
N6 C63 C64 O4 1.3(9) . . . . ?
C62 C63 C64 O4 -177.6(5) . . . . ?
N6 C63 C64 C65 -179.2(5) . . . . ?
C62 C63 C64 C65 1.9(3) . . . . ?
N5 C62 C65 O3 -0.2(9) . . . . ?
C63 C62 C65 O3 -178.8(5) . . . . ?
N5 C62 C65 C64 -179.6(5) . . . . ?
C63 C62 C65 C64 1.9(3) . . . . ?
O4 C64 C65 O3 -1.7(9) . . . . ?
C63 C64 C65 O3 178.8(5) . . . . ?
O4 C64 C65 C62 177.7(5) . . . . ?
C63 C64 C65 C62 -1.8(3) . . . . ?
C69 N8 C66 C67 40.8(5) . . . . ?
C70 N8 C66 C67 164.1(5) . . . . ?
N8 C66 C67 C68 -16.9(6) . . . . ?
C63 N6 C68 C69 -122.1(5) . . . . ?
C63 N6 C68 C67 124.8(5) . . . . ?
C66 C67 C68 N6 105.5(5) . . . . ?
C66 C67 C68 C69 -11.9(5) . . . . ?
C66 N8 C69 C68 -49.0(5) . . . . ?
C70 N8 C69 C68 -172.2(5) . . . . ?
N6 C68 C69 N8 -81.9(5) . . . . ?
C67 C68 C69 N8 36.9(5) . . . . ?
