#------------------------------------------------------------------------------
#$Date: 2024-07-05 17:08:14 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292867 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/15/1571529.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_1571529
loop_
_publ_author_name
'Grzelak, Magdalena'
'Kumar, Dharmendra'
'Kochman, Michał Andrzej'
'Morawiak, Maja'
'Wiosna-Sałyga, Gabriela'
'Kubas, Adam'
'Data, Przemysław'
'Lindner, Marcin'
_publ_section_title
;
 An unprecedented roll-off ratio in high-performing red TADF OLED emitters
 featuring 2,3-indole-annulated naphthalene imide and auxiliary donors.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              8404
_journal_page_last               8413
_journal_paper_doi               10.1039/d4sc01391c
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C46 H41 N3 O2, C4 H8 O2'
_chemical_formula_sum            'C50 H49 N3 O4'
_chemical_formula_weight         755.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2023-08-25 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.757(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6094(6)
_cell_length_b                   9.5173(3)
_cell_length_c                   27.5112(9)
_cell_measurement_reflns_used    4320
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.73
_cell_measurement_theta_min      2.75
_cell_volume                     4205.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32567
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.734
_diffrn_reflns_theta_min         2.751
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.8840
_exptl_absorpt_correction_T_min  0.7010
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.641
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         7120
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0698
_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)+(0.0708P)²+3.4237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.2002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4320
_reflns_number_total             7120
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc01391c2.cif
_cod_data_source_block           MMG0153_10B_0m
_cod_depositor_comments
'Adding full bibliography for 1571528--1571532.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1571529
_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   0.701
_shelx_estimated_absorpt_t_max   0.884
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.79867(13) -0.1523(2) 0.15257(8) 0.0526(6) Uani 1 1 d . . . . .
O2 O 0.53223(15) -0.1412(3) 0.16494(10) 0.0683(7) Uani 1 1 d . . . . .
N1 N 0.94539(15) 0.2293(2) 0.27768(9) 0.0392(6) Uani 1 1 d . . . . .
N2 N 0.66563(15) -0.1472(3) 0.15915(9) 0.0434(6) Uani 1 1 d . . . . .
N3 N 0.87076(17) 0.5972(3) 0.41675(10) 0.0462(7) Uani 1 1 d . . . . .
C1 C 0.93738(19) 0.3253(3) 0.31390(11) 0.0390(7) Uani 1 1 d . . . . .
C2 C 0.9991(2) 0.3966(3) 0.34869(12) 0.0418(8) Uani 1 1 d . . . . .
C3 C 0.9753(2) 0.4844(3) 0.38215(12) 0.0466(8) Uani 1 1 d . . . . .
H3 H 1.0157 0.5315 0.4062 0.056 Uiso 1 1 calc R U . . .
C4 C 0.8915(2) 0.5040(3) 0.38062(12) 0.0433(8) Uani 1 1 d . . . . .
C5 C 0.8297(2) 0.4349(3) 0.34595(11) 0.0420(8) Uani 1 1 d . . . . .
H5 H 0.7740 0.4492 0.3452 0.050 Uiso 1 1 calc R U . . .
C6 C 0.85186(19) 0.3426(3) 0.31183(11) 0.0380(7) Uani 1 1 d . . . . .
C7 C 0.80677(18) 0.2476(3) 0.27387(11) 0.0376(7) Uani 1 1 d . . . . .
C8 C 0.86707(18) 0.1805(3) 0.25401(11) 0.0382(7) Uani 1 1 d . . . . .
C9 C 0.84663(18) 0.0747(3) 0.21800(11) 0.0383(7) Uani 1 1 d . . . . .
H9 H 0.8871 0.0360 0.2041 0.046 Uiso 1 1 calc R U . . .
C10 C 0.76567(18) 0.0285(3) 0.20337(11) 0.0369(7) Uani 1 1 d . . . . .
C11 C 0.70271(18) 0.0912(3) 0.22304(11) 0.0384(7) Uani 1 1 d . . . . .
C12 C 0.62059(19) 0.0377(3) 0.20861(12) 0.0447(8) Uani 1 1 d . . . . .
C13 C 0.5593(2) 0.0978(4) 0.22737(14) 0.0597(10) Uani 1 1 d . . . . .
H13 H 0.5054 0.0620 0.2182 0.072 Uiso 1 1 calc R U . . .
C14 C 0.5775(2) 0.2115(4) 0.25995(15) 0.0623(10) Uani 1 1 d . . . . .
H14 H 0.5353 0.2533 0.2715 0.075 Uiso 1 1 calc R U . . .
C15 C 0.6570(2) 0.2630(4) 0.27531(13) 0.0516(9) Uani 1 1 d . . . . .
H15 H 0.6682 0.3376 0.2978 0.062 Uiso 1 1 calc R U . . .
C16 C 0.72211(18) 0.2043(3) 0.25746(12) 0.0399(7) Uani 1 1 d . . . . .
C17 C 0.74662(19) -0.0944(3) 0.16997(11) 0.0407(7) Uani 1 1 d . . . . .
C18 C 0.6009(2) -0.0872(4) 0.17629(13) 0.0481(8) Uani 1 1 d . . . . .
C19 C 0.6508(2) -0.2823(4) 0.13428(14) 0.0509(9) Uani 1 1 d . . . . .
C20 C 0.6193(2) -0.2885(5) 0.08269(15) 0.0639(10) Uani 1 1 d . . . . .
C21 C 0.6077(3) -0.4239(6) 0.06112(19) 0.0888(15) Uani 1 1 d . . . . .
H21 H 0.5862 -0.4323 0.0266 0.107 Uiso 1 1 calc R U . . .
C22 C 0.6273(3) -0.5436(6) 0.0894(3) 0.1011(18) Uani 1 1 d . . . . .
C23 C 0.6579(3) -0.5300(5) 0.1403(2) 0.0985(16) Uani 1 1 d . . . . .
H23 H 0.6707 -0.6109 0.1597 0.118 Uiso 1 1 calc R U . . .
C24 C 0.6703(2) -0.4015(4) 0.16380(17) 0.0695(11) Uani 1 1 d . . . . .
C25 C 1.0229(2) 0.1744(3) 0.26999(14) 0.0521(9) Uani 1 1 d D . . . .
H25A H 1.0670 0.2410 0.2838 0.063 Uiso 1 1 calc R U . . .
H25B H 1.0177 0.1685 0.2341 0.063 Uiso 1 1 calc R U . . .
C26 C 1.0483(3) 0.0353(5) 0.2924(2) 0.0895(15) Uani 1 1 d D . . . .
H26A H 1.0022 -0.0291 0.2806 0.107 Uiso 1 1 calc R U . . .
H26B H 1.0942 0.0019 0.2797 0.107 Uiso 1 1 calc R U . . .
C27 C 1.0723(4) 0.0281(5) 0.3444(2) 0.123(2) Uani 1 1 d D . . . .
H27A H 1.0255 0.0551 0.3575 0.147 Uiso 1 1 calc R U . . .
H27B H 1.1167 0.0952 0.3568 0.147 Uiso 1 1 calc R U . . .
C28 C 1.1032(5) -0.1230(5) 0.3652(2) 0.140(3) Uani 1 1 d D . . . .
H28A H 1.0613 -0.1914 0.3510 0.210 Uiso 1 1 calc R U . . .
H28B H 1.1134 -0.1237 0.4011 0.210 Uiso 1 1 calc R U . . .
H28C H 1.1537 -0.1456 0.3560 0.210 Uiso 1 1 calc R U . . .
C29 C 0.5979(3) -0.1575(6) 0.05181(16) 0.0927(15) Uani 1 1 d . . . . .
H29A H 0.5531 -0.1095 0.0610 0.139 Uiso 1 1 calc R U . . .
H29B H 0.5811 -0.1819 0.0168 0.139 Uiso 1 1 calc R U . . .
H29C H 0.6457 -0.0972 0.0578 0.139 Uiso 1 1 calc R U . . .
C30 C 0.6134(4) -0.6865(6) 0.0633(3) 0.176(4) Uani 1 1 d . . . . .
H30A H 0.6604 -0.7461 0.0769 0.264 Uiso 1 1 calc R U . . .
H30B H 0.6071 -0.6742 0.0279 0.264 Uiso 1 1 calc R U . . .
H30C H 0.5640 -0.7288 0.0688 0.264 Uiso 1 1 calc R U . . .
C31 C 0.7033(3) -0.3914(5) 0.22007(18) 0.1013(16) Uani 1 1 d . . . . .
H31A H 0.6604 -0.3565 0.2345 0.152 Uiso 1 1 calc R U . . .
H31B H 0.7500 -0.3284 0.2280 0.152 Uiso 1 1 calc R U . . .
H31C H 0.7206 -0.4827 0.2335 0.152 Uiso 1 1 calc R U . . .
C32 C 0.85296(19) 0.5417(3) 0.46019(11) 0.0413(7) Uani 1 1 d . . . . .
C33 C 0.8483(2) 0.3977(3) 0.46681(13) 0.0568(9) Uani 1 1 d . . . . .
H33 H 0.8592 0.3367 0.4429 0.068 Uiso 1 1 calc R U . . .
C34 C 0.8275(3) 0.3445(4) 0.50850(14) 0.0650(11) Uani 1 1 d . . . . .
H34 H 0.8246 0.2477 0.5125 0.078 Uiso 1 1 calc R U . . .
C35 C 0.8113(2) 0.4320(4) 0.54398(14) 0.0625(10) Uani 1 1 d . . . . .
H35 H 0.7960 0.3956 0.5717 0.075 Uiso 1 1 calc R U . . .
C36 C 0.8178(2) 0.5750(4) 0.53835(12) 0.0531(9) Uani 1 1 d . . . . .
H36 H 0.8076 0.6344 0.5629 0.064 Uiso 1 1 calc R U . . .
C37 C 0.83918(19) 0.6330(3) 0.49714(11) 0.0411(7) Uani 1 1 d . . . . .
C38 C 0.8553(2) 0.7901(3) 0.49457(12) 0.0511(9) Uani 1 1 d . . . . .
C39 C 0.8449(2) 0.8353(3) 0.44020(12) 0.0473(8) Uani 1 1 d . . . . .
C40 C 0.8299(3) 0.9732(4) 0.42539(15) 0.0768(13) Uani 1 1 d . . . . .
H40 H 0.8221 1.0386 0.4489 0.092 Uiso 1 1 calc R U . . .
C41 C 0.8258(3) 1.0181(4) 0.37765(16) 0.0951(16) Uani 1 1 d . . . . .
H41 H 0.8164 1.1123 0.3692 0.114 Uiso 1 1 calc R U . . .
C42 C 0.8359(3) 0.9224(4) 0.34244(16) 0.0816(13) Uani 1 1 d . . . . .
H42 H 0.8327 0.9516 0.3097 0.098 Uiso 1 1 calc R U . . .
C43 C 0.8507(2) 0.7845(4) 0.35516(13) 0.0584(10) Uani 1 1 d . . . . .
H43 H 0.8576 0.7202 0.3311 0.070 Uiso 1 1 calc R U . . .
C44 C 0.85566(19) 0.7387(3) 0.40440(12) 0.0423(8) Uani 1 1 d . . . . .
C45 C 0.7964(3) 0.8738(4) 0.51834(17) 0.0948(16) Uani 1 1 d . . . . .
H45A H 0.8077 0.9723 0.5167 0.142 Uiso 1 1 calc R U . . .
H45B H 0.8048 0.8462 0.5528 0.142 Uiso 1 1 calc R U . . .
H45C H 0.7398 0.8551 0.5004 0.142 Uiso 1 1 calc R U . . .
C46 C 0.9463(3) 0.8179(5) 0.52264(16) 0.0896(15) Uani 1 1 d . . . . .
H46A H 0.9824 0.7675 0.5065 0.134 Uiso 1 1 calc R U . . .
H46B H 0.9557 0.7868 0.5568 0.134 Uiso 1 1 calc R U . . .
H46C H 0.9577 0.9167 0.5221 0.134 Uiso 1 1 calc R U . . .
H2 H 1.0549(18) 0.382(3) 0.3513(10) 0.033(8) Uiso 1 1 d . . . . .
O51 O 0.6043(3) 0.7390(8) 0.39453(19) 0.1478(18) Uani 1 1 d . . . . .
O52 O 0.6477(2) 0.5946(6) 0.34372(19) 0.162(2) Uani 1 1 d . . . . .
C51 C 0.5887(5) 0.9882(11) 0.3863(4) 0.211(4) Uani 1 1 d . . . . .
H51A H 0.6398 1.0364 0.4013 0.317 Uiso 1 1 calc R U . . .
H51B H 0.5611 0.9644 0.4119 0.317 Uiso 1 1 calc R U . . .
H51C H 0.5533 1.0480 0.3618 0.317 Uiso 1 1 calc R U . . .
C52 C 0.6074(6) 0.8555(12) 0.3610(3) 0.179(3) Uani 1 1 d . . . . .
H52A H 0.5666 0.8423 0.3292 0.214 Uiso 1 1 calc R U . . .
H52B H 0.6621 0.8615 0.3547 0.214 Uiso 1 1 calc R U . . .
C54 C 0.6274(3) 0.6088(11) 0.3833(3) 0.139(3) Uani 1 1 d . . . . .
C56 C 0.6238(4) 0.5000(10) 0.4202(3) 0.165(3) Uani 1 1 d . . . . .
H56A H 0.6221 0.4092 0.4048 0.248 Uiso 1 1 calc R U . . .
H56B H 0.5746 0.5130 0.4320 0.248 Uiso 1 1 calc R U . . .
H56C H 0.6722 0.5064 0.4480 0.248 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 0.0181 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 N1 C1 108.1(2) . . ?
C8 N1 C25 125.1(3) . . ?
C1 N1 C25 126.4(3) . . ?
C17 N2 C18 124.3(3) . . ?
C17 N2 C19 117.3(2) . . ?
C18 N2 C19 117.9(3) . . ?
C44 N3 C32 120.4(3) . . ?
C44 N3 C4 119.1(2) . . ?
C32 N3 C4 119.7(2) . . ?
N1 C1 C2 129.1(3) . . ?
N1 C1 C6 109.1(3) . . ?
C2 C1 C6 121.8(3) . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2 119.7(17) . . ?
C1 C2 H2 122.0(17) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 N3 120.4(3) . . ?
C3 C4 N3 118.3(3) . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 134.7(3) . . ?
C1 C6 C7 106.7(3) . . ?
C8 C7 C16 119.2(3) . . ?
C8 C7 C6 106.0(3) . . ?
C16 C7 C6 134.5(3) . . ?
N1 C8 C9 127.5(3) . . ?
N1 C8 C7 110.0(3) . . ?
C9 C8 C7 122.3(3) . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 120.8(3) . . ?
C9 C10 C17 118.4(3) . . ?
C11 C10 C17 120.5(3) . . ?
C16 C11 C12 120.0(3) . . ?
C16 C11 C10 120.6(3) . . ?
C12 C11 C10 119.4(3) . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 C18 119.3(3) . . ?
C11 C12 C18 120.8(3) . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 118.0(3) . . ?
C15 C16 C7 123.9(3) . . ?
C11 C16 C7 118.1(3) . . ?
O1 C17 N2 119.7(3) . . ?
O1 C17 C10 122.8(3) . . ?
N2 C17 C10 117.5(3) . . ?
O2 C18 N2 119.4(3) . . ?
O2 C18 C12 123.2(3) . . ?
N2 C18 C12 117.4(3) . . ?
C20 C19 C24 122.6(4) . . ?
C20 C19 N2 119.8(3) . . ?
C24 C19 N2 117.7(3) . . ?
C19 C20 C21 116.4(4) . . ?
C19 C20 C29 121.3(4) . . ?
C21 C20 C29 122.3(4) . . ?
C22 C21 C20 122.2(5) . . ?
C22 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C23 C22 C21 118.3(5) . . ?
C23 C22 C30 122.5(6) . . ?
C21 C22 C30 119.2(6) . . ?
C22 C23 C24 122.5(5) . . ?
C22 C23 H23 118.7 . . ?
C24 C23 H23 118.7 . . ?
C23 C24 C19 117.9(4) . . ?
C23 C24 C31 120.8(4) . . ?
C19 C24 C31 121.3(4) . . ?
N1 C25 C26 115.5(3) . . ?
N1 C25 H25A 108.4 . . ?
C26 C25 H25A 108.4 . . ?
N1 C25 H25B 108.4 . . ?
C26 C25 H25B 108.4 . . ?
H25A C25 H25B 107.5 . . ?
C27 C26 C25 116.9(4) . . ?
C27 C26 H26A 108.1 . . ?
C25 C26 H26A 108.1 . . ?
C27 C26 H26B 108.1 . . ?
C25 C26 H26B 108.1 . . ?
H26A C26 H26B 107.3 . . ?
C26 C27 C28 113.5(5) . . ?
C26 C27 H27A 108.9 . . ?
C28 C27 H27A 108.9 . . ?
C26 C27 H27B 108.9 . . ?
C28 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C20 C29 H29A 109.5 . . ?
C20 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C20 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C22 C30 H30A 109.5 . . ?
C22 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C22 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C24 C31 H31A 109.5 . . ?
C24 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C24 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C37 119.5(3) . . ?
C33 C32 N3 120.9(3) . . ?
C37 C32 N3 119.6(3) . . ?
C34 C33 C32 120.5(3) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 120.6(3) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 119.2(3) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C35 C36 C37 122.0(3) . . ?
C35 C36 H36 119.0 . . ?
C37 C36 H36 119.0 . . ?
C36 C37 C32 118.1(3) . . ?
C36 C37 C38 120.9(3) . . ?
C32 C37 C38 120.8(3) . . ?
C39 C38 C37 110.2(3) . . ?
C39 C38 C45 110.4(3) . . ?
C37 C38 C45 110.6(3) . . ?
C39 C38 C46 107.2(3) . . ?
C37 C38 C46 107.9(3) . . ?
C45 C38 C46 110.5(4) . . ?
C40 C39 C44 117.8(3) . . ?
C40 C39 C38 121.7(3) . . ?
C44 C39 C38 120.4(3) . . ?
C41 C40 C39 122.9(4) . . ?
C41 C40 H40 118.6 . . ?
C39 C40 H40 118.6 . . ?
C40 C41 C42 119.1(4) . . ?
C40 C41 H41 120.4 . . ?
C42 C41 H41 120.4 . . ?
C43 C42 C41 120.3(4) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C42 C43 C44 120.5(3) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C39 C44 N3 120.8(3) . . ?
C39 C44 C43 119.4(3) . . ?
N3 C44 C43 119.8(3) . . ?
C38 C45 H45A 109.5 . . ?
C38 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C38 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C38 C46 H46A 109.5 . . ?
C38 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C38 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C54 O51 C52 119.7(7) . . ?
C52 C51 H51A 109.5 . . ?
C52 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C52 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O51 C52 C51 107.5(8) . . ?
O51 C52 H52A 110.2 . . ?
C51 C52 H52A 110.2 . . ?
O51 C52 H52B 110.2 . . ?
C51 C52 H52B 110.2 . . ?
H52A C52 H52B 108.5 . . ?
O52 C54 O51 117.4(10) . . ?
O52 C54 C56 127.4(9) . . ?
O51 C54 C56 115.2(7) . . ?
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 . . ?
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 C17 1.221(3) . ?
O2 C18 1.216(4) . ?
N1 C8 1.379(4) . ?
N1 C1 1.383(4) . ?
N1 C25 1.455(4) . ?
N2 C17 1.395(4) . ?
N2 C18 1.402(4) . ?
N2 C19 1.448(4) . ?
N3 C44 1.396(4) . ?
N3 C32 1.405(4) . ?
N3 C4 1.438(4) . ?
C1 C2 1.388(4) . ?
C1 C6 1.417(4) . ?
C2 C3 1.374(4) . ?
C2 H2 0.92(3) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C5 C6 1.401(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(4) . ?
C7 C8 1.410(4) . ?
C7 C16 1.424(4) . ?
C8 C9 1.392(4) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.425(4) . ?
C10 C17 1.472(4) . ?
C11 C16 1.416(4) . ?
C11 C12 1.415(4) . ?
C12 C13 1.378(4) . ?
C12 C18 1.470(5) . ?
C13 C14 1.389(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.412(4) . ?
C15 H15 0.9300 . ?
C19 C20 1.383(5) . ?
C19 C24 1.384(5) . ?
C20 C21 1.411(6) . ?
C20 C29 1.500(6) . ?
C21 C22 1.372(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(7) . ?
C22 C30 1.527(7) . ?
C23 C24 1.375(6) . ?
C23 H23 0.9300 . ?
C24 C31 1.508(6) . ?
C25 C26 1.475(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.386(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.584(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.387(4) . ?
C32 C37 1.399(4) . ?
C33 C34 1.376(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.361(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.377(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.386(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.524(4) . ?
C38 C39 1.523(4) . ?
C38 C45 1.531(5) . ?
C38 C46 1.535(5) . ?
C39 C40 1.378(5) . ?
C39 C44 1.391(4) . ?
C40 C41 1.366(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.371(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.364(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.405(4) . ?
C43 H43 0.9300 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
O51 C54 1.356(8) . ?
O51 C52 1.451(9) . ?
O52 C54 1.227(7) . ?
C51 C52 1.512(11) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C54 C56 1.461(10) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
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
C2 H2 O1 0.92(3) 2.48(3) 3.401(4) 173(2) 2_755
C5 H5 O52 0.93 2.50 3.370(5) 154.9 .
C5 H5 O52 0.93 2.50 3.370(5) 154.9 .
C2 H2 O1 0.92(3) 2.48(3) 3.401(4) 173(2) 2_755
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
C8 N1 C1 C2 176.5(3) . . . . ?
C25 N1 C1 C2 4.0(5) . . . . ?
C8 N1 C1 C6 -2.5(3) . . . . ?
C25 N1 C1 C6 -175.0(3) . . . . ?
N1 C1 C2 C3 -178.0(3) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C2 C3 C4 N3 179.9(3) . . . . ?
C44 N3 C4 C5 -89.3(4) . . . . ?
C32 N3 C4 C5 80.6(4) . . . . ?
C44 N3 C4 C3 91.6(4) . . . . ?
C32 N3 C4 C3 -98.5(3) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
N3 C4 C5 C6 -178.7(3) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C4 C5 C6 C7 174.9(3) . . . . ?
N1 C1 C6 C5 179.3(3) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
N1 C1 C6 C7 2.5(3) . . . . ?
C2 C1 C6 C7 -176.6(3) . . . . ?
C5 C6 C7 C8 -177.6(3) . . . . ?
C1 C6 C7 C8 -1.5(3) . . . . ?
C5 C6 C7 C16 -3.7(6) . . . . ?
C1 C6 C7 C16 172.4(3) . . . . ?
C1 N1 C8 C9 -174.5(3) . . . . ?
C25 N1 C8 C9 -1.9(5) . . . . ?
C1 N1 C8 C7 1.6(3) . . . . ?
C25 N1 C8 C7 174.2(3) . . . . ?
C16 C7 C8 N1 -175.0(2) . . . . ?
C6 C7 C8 N1 0.0(3) . . . . ?
C16 C7 C8 C9 1.3(4) . . . . ?
C6 C7 C8 C9 176.3(3) . . . . ?
N1 C8 C9 C10 171.8(3) . . . . ?
C7 C8 C9 C10 -3.8(4) . . . . ?
C8 C9 C10 C11 2.5(4) . . . . ?
C8 C9 C10 C17 -172.8(3) . . . . ?
C9 C10 C11 C16 1.1(4) . . . . ?
C17 C10 C11 C16 176.3(3) . . . . ?
C9 C10 C11 C12 -177.7(3) . . . . ?
C17 C10 C11 C12 -2.5(4) . . . . ?
C16 C11 C12 C13 1.3(5) . . . . ?
C10 C11 C12 C13 -179.9(3) . . . . ?
C16 C11 C12 C18 -174.8(3) . . . . ?
C10 C11 C12 C18 4.0(4) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
C18 C12 C13 C14 176.8(3) . . . . ?
C12 C13 C14 C15 -2.2(6) . . . . ?
C13 C14 C15 C16 1.7(6) . . . . ?
C14 C15 C16 C11 0.3(5) . . . . ?
C14 C15 C16 C7 -176.5(3) . . . . ?
C12 C11 C16 C15 -1.7(4) . . . . ?
C10 C11 C16 C15 179.5(3) . . . . ?
C12 C11 C16 C7 175.2(3) . . . . ?
C10 C11 C16 C7 -3.6(4) . . . . ?
C8 C7 C16 C15 179.2(3) . . . . ?
C6 C7 C16 C15 5.9(5) . . . . ?
C8 C7 C16 C11 2.4(4) . . . . ?
C6 C7 C16 C11 -170.9(3) . . . . ?
C18 N2 C17 O1 -178.6(3) . . . . ?
C19 N2 C17 O1 9.9(4) . . . . ?
C18 N2 C17 C10 2.8(4) . . . . ?
C19 N2 C17 C10 -168.7(3) . . . . ?
C9 C10 C17 O1 -4.1(4) . . . . ?
C11 C10 C17 O1 -179.4(3) . . . . ?
C9 C10 C17 N2 174.5(3) . . . . ?
C11 C10 C17 N2 -0.8(4) . . . . ?
C17 N2 C18 O2 -179.8(3) . . . . ?
C19 N2 C18 O2 -8.3(5) . . . . ?
C17 N2 C18 C12 -1.3(4) . . . . ?
C19 N2 C18 C12 170.2(3) . . . . ?
C13 C12 C18 O2 0.1(5) . . . . ?
C11 C12 C18 O2 176.2(3) . . . . ?
C13 C12 C18 N2 -178.3(3) . . . . ?
C11 C12 C18 N2 -2.2(4) . . . . ?
C17 N2 C19 C20 -97.4(4) . . . . ?
C18 N2 C19 C20 90.6(4) . . . . ?
C17 N2 C19 C24 81.8(4) . . . . ?
C18 N2 C19 C24 -90.3(4) . . . . ?
C24 C19 C20 C21 0.0(5) . . . . ?
N2 C19 C20 C21 179.1(3) . . . . ?
C24 C19 C20 C29 179.3(4) . . . . ?
N2 C19 C20 C29 -1.6(5) . . . . ?
C19 C20 C21 C22 -0.6(6) . . . . ?
C29 C20 C21 C22 -179.9(4) . . . . ?
C20 C21 C22 C23 0.9(7) . . . . ?
C20 C21 C22 C30 -179.7(4) . . . . ?
C21 C22 C23 C24 -0.6(8) . . . . ?
C30 C22 C23 C24 -180.0(5) . . . . ?
C22 C23 C24 C19 0.0(7) . . . . ?
C22 C23 C24 C31 179.3(5) . . . . ?
C20 C19 C24 C23 0.3(6) . . . . ?
N2 C19 C24 C23 -178.8(4) . . . . ?
C20 C19 C24 C31 -179.0(4) . . . . ?
N2 C19 C24 C31 1.9(6) . . . . ?
C8 N1 C25 C26 -72.9(4) . . . . ?
C1 N1 C25 C26 98.4(4) . . . . ?
N1 C25 C26 C27 -68.5(6) . . . . ?
C25 C26 C27 C28 -176.8(5) . . . . ?
C44 N3 C32 C33 164.3(3) . . . . ?
C4 N3 C32 C33 -5.4(5) . . . . ?
C44 N3 C32 C37 -15.2(4) . . . . ?
C4 N3 C32 C37 175.1(3) . . . . ?
C37 C32 C33 C34 2.1(5) . . . . ?
N3 C32 C33 C34 -177.4(3) . . . . ?
C32 C33 C34 C35 0.0(6) . . . . ?
C33 C34 C35 C36 -1.6(6) . . . . ?
C34 C35 C36 C37 1.1(6) . . . . ?
C35 C36 C37 C32 1.0(5) . . . . ?
C35 C36 C37 C38 -173.2(3) . . . . ?
C33 C32 C37 C36 -2.6(5) . . . . ?
N3 C32 C37 C36 177.0(3) . . . . ?
C33 C32 C37 C38 171.7(3) . . . . ?
N3 C32 C37 C38 -8.8(4) . . . . ?
C36 C37 C38 C39 -158.6(3) . . . . ?
C32 C37 C38 C39 27.3(4) . . . . ?
C36 C37 C38 C45 -36.3(5) . . . . ?
C32 C37 C38 C45 149.6(3) . . . . ?
C36 C37 C38 C46 84.6(4) . . . . ?
C32 C37 C38 C46 -89.5(4) . . . . ?
C37 C38 C39 C40 159.2(3) . . . . ?
C45 C38 C39 C40 36.8(5) . . . . ?
C46 C38 C39 C40 -83.6(4) . . . . ?
C37 C38 C39 C44 -25.0(4) . . . . ?
C45 C38 C39 C44 -147.4(3) . . . . ?
C46 C38 C39 C44 92.2(4) . . . . ?
C44 C39 C40 C41 -0.5(7) . . . . ?
C38 C39 C40 C41 175.5(4) . . . . ?
C39 C40 C41 C42 0.9(8) . . . . ?
C40 C41 C42 C43 -0.7(8) . . . . ?
C41 C42 C43 C44 0.1(7) . . . . ?
C40 C39 C44 N3 -179.8(3) . . . . ?
C38 C39 C44 N3 4.2(5) . . . . ?
C40 C39 C44 C43 -0.2(5) . . . . ?
C38 C39 C44 C43 -176.2(3) . . . . ?
C32 N3 C44 C39 17.7(5) . . . . ?
C4 N3 C44 C39 -172.6(3) . . . . ?
C32 N3 C44 C43 -161.9(3) . . . . ?
C4 N3 C44 C43 7.8(5) . . . . ?
C42 C43 C44 C39 0.4(5) . . . . ?
C42 C43 C44 N3 180.0(4) . . . . ?
C54 O51 C52 C51 -173.1(6) . . . . ?
C52 O51 C54 O52 -2.4(9) . . . . ?
C52 O51 C54 C56 178.6(6) . . . . ?
