#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:51:01 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/96/1559612.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_1559612
loop_
_publ_author_name
'Rausch, Rodger'
'Röhr, Merle I S'
'Schmidt, David'
'Krummenacher, Ivo'
'Braunschweig, Holger'
'Würthner, Frank'
_publ_section_title
;
 Tuning phenoxyl-substituted diketopyrrolopyrroles from quinoidal to
 biradical ground states through (hetero-)aromatic linkers.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              793
_journal_page_last               802
_journal_paper_doi               10.1039/d0sc05475e
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C62 H84 N2 O4'
_chemical_formula_sum            'C62 H84 N2 O4'
_chemical_formula_weight         921.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-05-06 deposited with the CCDC.	2020-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                118.5760(10)
_cell_angle_beta                 101.4230(10)
_cell_angle_gamma                94.6720(10)
_cell_formula_units_Z            1
_cell_length_a                   9.8347(4)
_cell_length_b                   12.6226(5)
_cell_length_c                   12.8064(6)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.25
_cell_measurement_theta_min      4.05
_cell_volume                     1339.49(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_Photon100
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20630
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.294
_diffrn_reflns_theta_min         4.054
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_description       block
_exptl_crystal_F_000             502
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5260
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0464
_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)+(0.0565P)²+0.6920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4904
_reflns_number_total             5260
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc05475e2.cif
_cod_data_source_block           DPP1
_cod_depositor_comments
;Adding full bibliography for 1559612--1559613.cif.

 Adding full bibliography for 1559612--1559613.cif.
;
_cod_database_code               1559612
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.79345(10) 1.13134(9) 0.14901(9) 0.0277(2) Uani 1 1 d . . . . .
N1 N 0.62615(11) 0.99228(10) 0.15124(10) 0.0220(2) Uani 1 1 d . . . . .
C1 C 0.67404(13) 1.06653(11) 0.10514(12) 0.0204(3) Uani 1 1 d . . . . .
O2 O -0.03337(11) 0.35631(9) 0.26597(10) 0.0280(2) Uani 1 1 d . . . . .
H2 H -0.077(2) 0.288(2) 0.2081(16) 0.042 Uiso 1 1 calc R U . . .
C2 C 0.44402(12) 0.95766(11) -0.00405(11) 0.0178(3) Uani 1 1 d . . . . .
C3 C 0.48784(13) 0.92634(11) 0.08480(12) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.41046(13) 0.83581(11) 0.10392(11) 0.0197(3) Uani 1 1 d . . . . .
C6 C 0.18407(13) 0.73194(12) 0.09111(12) 0.0202(3) Uani 1 1 d . . . . .
H6 H 0.0838 0.7220 0.0727 0.024 Uiso 1 1 calc R U . . .
C5 C 0.26246(13) 0.81929(12) 0.07854(12) 0.0202(3) Uani 1 1 d . . . . .
H5 H 0.2153 0.8687 0.0523 0.024 Uiso 1 1 calc R U . . .
C7 C 0.24969(13) 0.65798(11) 0.13054(11) 0.0195(3) Uani 1 1 d . . . . .
C9 C 0.47607(13) 0.75891(12) 0.13863(12) 0.0230(3) Uani 1 1 d . . . . .
H9 H 0.5758 0.7659 0.1529 0.028 Uiso 1 1 calc R U . . .
C8 C 0.39701(13) 0.67253(12) 0.15239(12) 0.0227(3) Uani 1 1 d . . . . .
H8 H 0.4440 0.6221 0.1772 0.027 Uiso 1 1 calc R U . . .
C10 C 0.16779(13) 0.57088(11) 0.15362(11) 0.0186(3) Uani 1 1 d . . . . .
C11 C 0.04885(13) 0.59818(11) 0.19692(11) 0.0196(3) Uani 1 1 d . . . . .
H11 H 0.0154 0.6690 0.2034 0.023 Uiso 1 1 calc R U . . .
C12 C -0.02298(12) 0.52528(11) 0.23118(11) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.02909(13) 0.42076(11) 0.22066(11) 0.0184(3) Uani 1 1 d . . . . .
C14 C 0.14752(13) 0.38828(11) 0.17466(11) 0.0188(3) Uani 1 1 d . . . . .
C15 C 0.21327(13) 0.46503(11) 0.14102(11) 0.0195(3) Uani 1 1 d . . . . .
H15 H 0.2921 0.4441 0.1083 0.023 Uiso 1 1 calc R U . . .
C16 C -0.15102(13) 0.56154(12) 0.28359(12) 0.0219(3) Uani 1 1 d . . . . .
C17 C -0.11561(16) 0.59416(15) 0.41902(13) 0.0313(3) Uani 1 1 d . . . . .
H17A H -0.1968 0.6189 0.4518 0.047 Uiso 1 1 calc R U . . .
H17B H -0.0330 0.6623 0.4673 0.047 Uiso 1 1 calc R U . . .
H17C H -0.0943 0.5221 0.4244 0.047 Uiso 1 1 calc R U . . .
C18 C -0.19098(16) 0.67443(14) 0.27870(16) 0.0331(3) Uani 1 1 d . . . . .
H18A H -0.2129 0.6565 0.1931 0.050 Uiso 1 1 calc R U . . .
H18B H -0.1114 0.7450 0.3297 0.050 Uiso 1 1 calc R U . . .
H18C H -0.2742 0.6938 0.3101 0.050 Uiso 1 1 calc R U . . .
C19 C -0.28353(14) 0.45720(14) 0.20788(14) 0.0307(3) Uani 1 1 d . . . . .
H19A H -0.3046 0.4355 0.1212 0.046 Uiso 1 1 calc R U . . .
H19B H -0.3643 0.4848 0.2402 0.046 Uiso 1 1 calc R U . . .
H19C H -0.2660 0.3848 0.2141 0.046 Uiso 1 1 calc R U . . .
C20 C 0.20711(14) 0.27523(12) 0.16412(13) 0.0230(3) Uani 1 1 d . . . . .
C21 C 0.34373(15) 0.26869(14) 0.12349(17) 0.0354(4) Uani 1 1 d . . . . .
H21A H 0.3804 0.1978 0.1208 0.053 Uiso 1 1 calc R U . . .
H21B H 0.4143 0.3445 0.1824 0.053 Uiso 1 1 calc R U . . .
H21C H 0.3241 0.2596 0.0412 0.053 Uiso 1 1 calc R U . . .
C22 C 0.2436(2) 0.28188(17) 0.28967(16) 0.0434(4) Uani 1 1 d . . . . .
H22A H 0.2861 0.2118 0.2821 0.065 Uiso 1 1 calc R U . . .
H22B H 0.1571 0.2791 0.3160 0.065 Uiso 1 1 calc R U . . .
H22C H 0.3110 0.3590 0.3509 0.065 Uiso 1 1 calc R U . . .
C23 C 0.10179(15) 0.15506(13) 0.06785(15) 0.0319(3) Uani 1 1 d . . . . .
H23A H 0.0800 0.1507 -0.0123 0.048 Uiso 1 1 calc R U . . .
H23B H 0.0145 0.1527 0.0933 0.048 Uiso 1 1 calc R U . . .
H23C H 0.1435 0.0848 0.0609 0.048 Uiso 1 1 calc R U . . .
C31 C 0.71003(16) 1.00956(16) 0.26820(15) 0.0361(4) Uani 0.504(2) 1 d D . P A 1
H31A H 0.8093 1.0494 0.2858 0.043 Uiso 0.504(2) 1 calc R U P A 1
H31B H 0.7100 0.9286 0.2628 0.043 Uiso 0.504(2) 1 calc R U P A 1
C32 C 0.6398(5) 1.0984(4) 0.3820(4) 0.0244(9) Uani 0.504(2) 1 d D . P A 1
H32 H 0.5373 1.0614 0.3602 0.029 Uiso 0.504(2) 1 calc R U P A 1
C33 C 0.7218(4) 1.0961(3) 0.4976(3) 0.0280(7) Uani 0.504(2) 1 d D . P A 1
H33A H 0.8244 1.1250 0.5135 0.034 Uiso 0.504(2) 1 calc R U P A 1
H33B H 0.6919 1.1542 0.5701 0.034 Uiso 0.504(2) 1 calc R U P A 1
C34 C 0.6979(4) 0.9688(3) 0.4839(3) 0.0307(7) Uani 0.504(2) 1 d D . P A 1
H34A H 0.5953 0.9323 0.4497 0.037 Uiso 0.504(2) 1 calc R U P A 1
H34B H 0.7466 0.9155 0.4236 0.037 Uiso 0.504(2) 1 calc R U P A 1
C35 C 0.7504(4) 0.9683(3) 0.6038(3) 0.0370(8) Uani 0.504(2) 1 d D . P A 1
H35A H 0.7068 1.0261 0.6659 0.044 Uiso 0.504(2) 1 calc R U P A 1
H35B H 0.7169 0.8848 0.5888 0.044 Uiso 0.504(2) 1 calc R U P A 1
C36 C 0.9084(4) 1.0031(4) 0.6573(4) 0.0434(9) Uani 0.504(2) 1 d D . P A 1
H36A H 0.9532 0.9468 0.5966 0.065 Uiso 0.504(2) 1 calc R U P A 1
H36B H 0.9327 0.9973 0.7322 0.065 Uiso 0.504(2) 1 calc R U P A 1
H36C H 0.9424 1.0877 0.6779 0.065 Uiso 0.504(2) 1 calc R U P A 1
C37 C 0.6551(14) 1.2297(7) 0.4100(6) 0.0534(10) Uani 0.504(2) 1 d D . P A 1
H37A H 0.6114 1.2299 0.3335 0.064 Uiso 0.504(2) 1 calc R U P A 1
H37B H 0.7572 1.2670 0.4361 0.064 Uiso 0.504(2) 1 calc R U P A 1
C38 C 0.588(2) 1.3084(14) 0.5097(13) 0.079(3) Uani 0.504(2) 1 d D U P A 1
H38A H 0.5793 1.3849 0.5090 0.119 Uiso 0.504(2) 1 calc R U P A 1
H38B H 0.6465 1.3280 0.5904 0.119 Uiso 0.504(2) 1 calc R U P A 1
H38C H 0.4931 1.2632 0.4942 0.119 Uiso 0.504(2) 1 calc R U P A 1
C31B C 0.71003(16) 1.00956(16) 0.26820(15) 0.0361(4) Uani 0.239(2) 1 d D . P A
2
H31C H 0.8106 1.0134 0.2671 0.043 Uiso 0.239(2) 1 calc R U P A 2
H31D H 0.6791 0.9365 0.2742 0.043 Uiso 0.239(2) 1 calc R U P A 2
C32B C 0.7001(14) 1.1222(8) 0.3809(7) 0.046(3) Uani 0.239(2) 1 d D U P A 2
H32B H 0.6114 1.0893 0.3921 0.055 Uiso 0.239(2) 1 calc R U P A 2
C33B C 0.8108(12) 1.1324(7) 0.4937(6) 0.053(3) Uani 0.239(2) 1 d D . P A 2
H33C H 0.9027 1.1227 0.4736 0.064 Uiso 0.239(2) 1 calc R U P A 2
H33D H 0.8245 1.2161 0.5657 0.064 Uiso 0.239(2) 1 calc R U P A 2
C34B C 0.7696(12) 1.0381(10) 0.5304(10) 0.0524(18) Uani 0.239(2) 1 d D . P A 2
H34C H 0.6849 1.0551 0.5617 0.063 Uiso 0.239(2) 1 calc R U P A 2
H34D H 0.7434 0.9549 0.4559 0.063 Uiso 0.239(2) 1 calc R U P A 2
C35B C 0.8851(9) 1.0387(7) 0.6272(7) 0.0386(18) Uani 0.239(2) 1 d D . P A 2
H35C H 0.9707 1.0244 0.5968 0.046 Uiso 0.239(2) 1 calc R U P A 2
H35D H 0.9092 1.1213 0.7024 0.046 Uiso 0.239(2) 1 calc R U P A 2
C36B C 0.8473(9) 0.9437(7) 0.6612(6) 0.0400(17) Uani 0.239(2) 1 d D . P A 2
H36D H 0.8208 0.8616 0.5870 0.060 Uiso 0.239(2) 1 calc R U P A 2
H36E H 0.7674 0.9609 0.6978 0.060 Uiso 0.239(2) 1 calc R U P A 2
H36F H 0.9290 0.9466 0.7211 0.060 Uiso 0.239(2) 1 calc R U P A 2
C37B C 0.662(3) 1.2303(15) 0.3815(15) 0.0534(10) Uani 0.239(2) 1 d D . P A 2
H37C H 0.5834 1.2038 0.3068 0.064 Uiso 0.239(2) 1 calc R U P A 2
H37D H 0.7439 1.2767 0.3763 0.064 Uiso 0.239(2) 1 calc R U P A 2
C38B C 0.616(5) 1.316(3) 0.494(3) 0.079(3) Uani 0.239(2) 1 d D U P A 2
H38D H 0.5747 1.3778 0.4806 0.119 Uiso 0.239(2) 1 calc R U P A 2
H38E H 0.6990 1.3573 0.5664 0.119 Uiso 0.239(2) 1 calc R U P A 2
H38F H 0.5460 1.2683 0.5083 0.119 Uiso 0.239(2) 1 calc R U P A 2
C31C C 0.71003(16) 1.00956(16) 0.26820(15) 0.0361(4) Uani 0.257(2) 1 d D . P A
3
H31E H 0.7586 0.9391 0.2449 0.043 Uiso 0.257(2) 1 calc R U P A 3
H31F H 0.7852 1.0835 0.3018 0.043 Uiso 0.257(2) 1 calc R U P A 3
C32C C 0.6655(6) 1.0222(7) 0.3666(5) 0.0338(14) Uani 0.257(2) 1 d D . P A 3
H32C H 0.5893 0.9490 0.3373 0.041 Uiso 0.257(2) 1 calc R U P A 3
C33C C 0.5914(7) 1.1437(5) 0.4000(4) 0.0204(12) Uani 0.257(2) 1 d D . P A 3
H33E H 0.5263 1.1324 0.3242 0.024 Uiso 0.257(2) 1 calc R U P A 3
H33F H 0.5359 1.1534 0.4596 0.024 Uiso 0.257(2) 1 calc R U P A 3
C34C C 0.7096(11) 1.2592(8) 0.4564(9) 0.0534(10) Uani 0.257(2) 1 d D . P A 3
H34E H 0.7662 1.2786 0.5388 0.064 Uiso 0.257(2) 1 calc R U P A 3
H34F H 0.7735 1.2457 0.4024 0.064 Uiso 0.257(2) 1 calc R U P A 3
C35C C 0.6341(7) 1.3650(7) 0.4674(6) 0.0380(15) Uani 0.257(2) 1 d D . P A 3
H35E H 0.5760 1.3436 0.3848 0.046 Uiso 0.257(2) 1 calc R U P A 3
H35F H 0.7055 1.4411 0.4998 0.046 Uiso 0.257(2) 1 calc R U P A 3
C36C C 0.5385(6) 1.3875(6) 0.5550(6) 0.0372(15) Uani 0.257(2) 1 d D . P A 3
H36G H 0.4934 1.4566 0.5638 0.056 Uiso 0.257(2) 1 calc R U P A 3
H36H H 0.5961 1.4069 0.6362 0.056 Uiso 0.257(2) 1 calc R U P A 3
H36I H 0.4654 1.3132 0.5208 0.056 Uiso 0.257(2) 1 calc R U P A 3
C37C C 0.7843(8) 1.0311(6) 0.4722(8) 0.047(2) Uani 0.257(2) 1 d D . P A 3
H37E H 0.8257 0.9566 0.4380 0.056 Uiso 0.257(2) 1 calc R U P A 3
H37F H 0.8602 1.1032 0.5011 0.056 Uiso 0.257(2) 1 calc R U P A 3
C38C C 0.7390(11) 1.0425(9) 0.5775(7) 0.0524(18) Uani 0.257(2) 1 d D . P A 3
H38G H 0.6674 0.9695 0.5510 0.079 Uiso 0.257(2) 1 calc R U P A 3
H38H H 0.6983 1.1163 0.6127 0.079 Uiso 0.257(2) 1 calc R U P A 3
H38I H 0.8206 1.0495 0.6401 0.079 Uiso 0.257(2) 1 calc R U P A 3
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
C3 N1 C1 111.19(10) . . ?
C3 N1 C31C 128.49(11) . . ?
C1 N1 C31C 119.27(10) . . ?
C3 N1 C31 128.49(11) . . ?
C1 N1 C31 119.27(10) . . ?
C3 N1 C31B 128.49(11) . . ?
C1 N1 C31B 119.27(10) . . ?
O1 C1 N1 122.29(11) . . ?
O1 C1 C2 133.28(11) . 2_675 ?
N1 C1 C2 104.42(10) . 2_675 ?
C13 O2 H2 109.5 . . ?
C3 C2 C2 109.40(14) . 2_675 ?
C3 C2 C1 142.79(11) . 2_675 ?
C2 C2 C1 107.79(13) 2_675 2_675 ?
C2 C3 N1 107.19(10) . . ?
C2 C3 C4 127.78(11) . . ?
N1 C3 C4 124.93(11) . . ?
C9 C4 C5 118.05(11) . . ?
C9 C4 C3 123.11(11) . . ?
C5 C4 C3 118.71(11) . . ?
C5 C6 C7 121.28(11) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C5 C4 120.92(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C8 C7 C6 117.50(11) . . ?
C8 C7 C10 120.78(11) . . ?
C6 C7 C10 121.68(11) . . ?
C8 C9 C4 120.68(12) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C9 C8 C7 121.50(12) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C15 C10 C11 118.37(11) . . ?
C15 C10 C7 121.08(11) . . ?
C11 C10 C7 120.39(11) . . ?
C10 C11 C12 122.31(11) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C11 C12 C13 117.59(11) . . ?
C11 C12 C16 120.70(11) . . ?
C13 C12 C16 121.67(11) . . ?
O2 C13 C12 117.25(11) . . ?
O2 C13 C14 120.66(11) . . ?
C12 C13 C14 121.91(11) . . ?
C15 C14 C13 117.28(11) . . ?
C15 C14 C20 120.10(11) . . ?
C13 C14 C20 122.60(11) . . ?
C10 C15 C14 122.49(11) . . ?
C10 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C17 C16 C18 107.72(12) . . ?
C17 C16 C19 109.76(11) . . ?
C18 C16 C19 106.34(11) . . ?
C17 C16 C12 110.21(11) . . ?
C18 C16 C12 111.26(10) . . ?
C19 C16 C12 111.42(11) . . ?
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 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C23 106.66(12) . . ?
C21 C20 C22 106.69(13) . . ?
C23 C20 C22 109.81(12) . . ?
C21 C20 C14 111.68(10) . . ?
C23 C20 C14 111.14(11) . . ?
C22 C20 C14 110.69(11) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C31 C32 109.17(18) . . ?
N1 C31 H31A 109.8 . . ?
C32 C31 H31A 109.8 . . ?
N1 C31 H31B 109.8 . . ?
C32 C31 H31B 109.8 . . ?
H31A C31 H31B 108.3 . . ?
C37 C32 C33 109.4(4) . . ?
C37 C32 C31 113.6(4) . . ?
C33 C32 C31 105.3(3) . . ?
C37 C32 H32 109.5 . . ?
C33 C32 H32 109.5 . . ?
C31 C32 H32 109.5 . . ?
C34 C33 C32 113.3(3) . . ?
C34 C33 H33A 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C35 C34 C33 114.4(3) . . ?
C35 C34 H34A 108.7 . . ?
C33 C34 H34A 108.7 . . ?
C35 C34 H34B 108.7 . . ?
C33 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
C36 C35 C34 115.1(3) . . ?
C36 C35 H35A 108.5 . . ?
C34 C35 H35A 108.5 . . ?
C36 C35 H35B 108.5 . . ?
C34 C35 H35B 108.5 . . ?
H35A C35 H35B 107.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C32 C37 C38 113.5(9) . . ?
C32 C37 H37A 108.9 . . ?
C38 C37 H37A 108.9 . . ?
C32 C37 H37B 108.9 . . ?
C38 C37 H37B 108.9 . . ?
H37A C37 H37B 107.7 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N1 C31B C32B 115.0(3) . . ?
N1 C31B H31C 108.5 . . ?
C32B C31B H31C 108.5 . . ?
N1 C31B H31D 108.5 . . ?
C32B C31B H31D 108.5 . . ?
H31C C31B H31D 107.5 . . ?
C37B C32B C31B 123.9(8) . . ?
C37B C32B C33B 121.3(11) . . ?
C31B C32B C33B 106.9(6) . . ?
C37B C32B H32B 99.3 . . ?
C31B C32B H32B 99.3 . . ?
C33B C32B H32B 99.3 . . ?
C34B C33B C32B 114.7(8) . . ?
C34B C33B H33C 108.6 . . ?
C32B C33B H33C 108.6 . . ?
C34B C33B H33D 108.6 . . ?
C32B C33B H33D 108.6 . . ?
H33C C33B H33D 107.6 . . ?
C35B C34B C33B 113.7(8) . . ?
C35B C34B H34C 108.8 . . ?
C33B C34B H34C 108.8 . . ?
C35B C34B H34D 108.8 . . ?
C33B C34B H34D 108.8 . . ?
H34C C34B H34D 107.7 . . ?
C36B C35B C34B 114.1(7) . . ?
C36B C35B H35C 108.7 . . ?
C34B C35B H35C 108.7 . . ?
C36B C35B H35D 108.7 . . ?
C34B C35B H35D 108.7 . . ?
H35C C35B H35D 107.6 . . ?
C35B C36B H36D 109.5 . . ?
C35B C36B H36E 109.5 . . ?
H36D C36B H36E 109.5 . . ?
C35B C36B H36F 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?
C32B C37B C38B 114.3(17) . . ?
C32B C37B H37C 108.7 . . ?
C38B C37B H37C 108.7 . . ?
C32B C37B H37D 108.7 . . ?
C38B C37B H37D 108.7 . . ?
H37C C37B H37D 107.6 . . ?
C37B C38B H38D 109.5 . . ?
C37B C38B H38E 109.5 . . ?
H38D C38B H38E 109.5 . . ?
C37B C38B H38F 109.5 . . ?
H38D C38B H38F 109.5 . . ?
H38E C38B H38F 109.5 . . ?
C32C C31C N1 128.5(3) . . ?
C32C C31C H31E 105.2 . . ?
N1 C31C H31E 105.2 . . ?
C32C C31C H31F 105.2 . . ?
N1 C31C H31F 105.2 . . ?
H31E C31C H31F 105.9 . . ?
C31C C32C C37C 113.9(6) . . ?
C31C C32C C33C 101.0(4) . . ?
C37C C32C C33C 116.8(5) . . ?
C31C C32C H32C 108.2 . . ?
C37C C32C H32C 108.2 . . ?
C33C C32C H32C 108.2 . . ?
C34C C33C C32C 108.6(5) . . ?
C34C C33C H33E 110.0 . . ?
C32C C33C H33E 110.0 . . ?
C34C C33C H33F 110.0 . . ?
C32C C33C H33F 110.0 . . ?
H33E C33C H33F 108.3 . . ?
C35C C34C C33C 106.2(7) . . ?
C35C C34C H34E 110.5 . . ?
C33C C34C H34E 110.5 . . ?
C35C C34C H34F 110.5 . . ?
C33C C34C H34F 110.5 . . ?
H34E C34C H34F 108.7 . . ?
C34C C35C C36C 109.8(7) . . ?
C34C C35C H35E 109.7 . . ?
C36C C35C H35E 109.7 . . ?
C34C C35C H35F 109.7 . . ?
C36C C35C H35F 109.7 . . ?
H35E C35C H35F 108.2 . . ?
C35C C36C H36G 109.5 . . ?
C35C C36C H36H 109.5 . . ?
H36G C36C H36H 109.5 . . ?
C35C C36C H36I 109.5 . . ?
H36G C36C H36I 109.5 . . ?
H36H C36C H36I 109.5 . . ?
C38C C37C C32C 115.0(7) . . ?
C38C C37C H37E 108.5 . . ?
C32C C37C H37E 108.5 . . ?
C38C C37C H37F 108.5 . . ?
C32C C37C H37F 108.5 . . ?
H37E C37C H37F 107.5 . . ?
C37C C38C H38G 109.5 . . ?
C37C C38C H38H 109.5 . . ?
H38G C38C H38H 109.5 . . ?
C37C C38C H38I 109.5 . . ?
H38G C38C H38I 109.5 . . ?
H38H C38C H38I 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 C1 1.2274(16) . ?
N1 C3 1.3952(16) . ?
N1 C1 1.4200(15) . ?
N1 C31C 1.4630(17) . ?
N1 C31 1.4630(17) . ?
N1 C31B 1.4630(17) . ?
C1 C2 1.4442(18) 2_675 ?
O2 C13 1.3737(14) . ?
O2 H2 0.83(2) . ?
C2 C3 1.3787(18) . ?
C2 C2 1.422(2) 2_675 ?
C2 C1 1.4442(18) 2_675 ?
C3 C4 1.4645(16) . ?
C4 C9 1.3991(18) . ?
C4 C5 1.4021(17) . ?
C6 C5 1.3844(17) . ?
C6 C7 1.4012(18) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.3993(18) . ?
C7 C10 1.4851(16) . ?
C9 C8 1.3873(17) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C10 C15 1.3896(18) . ?
C10 C11 1.3908(18) . ?
C11 C12 1.3933(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4101(18) . ?
C12 C16 1.5429(17) . ?
C13 C14 1.4108(18) . ?
C14 C15 1.3963(17) . ?
C14 C20 1.5432(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.5340(19) . ?
C16 C18 1.5349(19) . ?
C16 C19 1.5399(18) . ?
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 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5286(19) . ?
C20 C23 1.5307(19) . ?
C20 C22 1.536(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C31 C32 1.679(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C37 1.506(7) . ?
C32 C33 1.553(5) . ?
C32 H32 1.0000 . ?
C33 C34 1.523(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.523(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.502(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.513(8) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C31B C32B 1.493(8) . ?
C31B H31C 0.9900 . ?
C31B H31D 0.9900 . ?
C32B C37B 1.443(11) . ?
C32B C33B 1.570(9) . ?
C32B H32B 1.0000 . ?
C33B C34B 1.527(11) . ?
C33B H33C 0.9900 . ?
C33B H33D 0.9900 . ?
C34B C35B 1.503(11) . ?
C34B H34C 0.9900 . ?
C34B H34D 0.9900 . ?
C35B C36B 1.503(9) . ?
C35B H35C 0.9900 . ?
C35B H35D 0.9900 . ?
C36B H36D 0.9800 . ?
C36B H36E 0.9800 . ?
C36B H36F 0.9800 . ?
C37B C38B 1.514(15) . ?
C37B H37C 0.9900 . ?
C37B H37D 0.9900 . ?
C38B H38D 0.9800 . ?
C38B H38E 0.9800 . ?
C38B H38F 0.9800 . ?
C31C C32C 1.358(6) . ?
C31C H31E 0.9900 . ?
C31C H31F 0.9900 . ?
C32C C37C 1.553(8) . ?
C32C C33C 1.656(9) . ?
C32C H32C 1.0000 . ?
C33C C34C 1.544(11) . ?
C33C H33E 0.9900 . ?
C33C H33F 0.9900 . ?
C34C C35C 1.542(10) . ?
C34C H34E 0.9900 . ?
C34C H34F 0.9900 . ?
C35C C36C 1.543(8) . ?
C35C H35E 0.9900 . ?
C35C H35F 0.9900 . ?
C36C H36G 0.9800 . ?
C36C H36H 0.9800 . ?
C36C H36I 0.9800 . ?
C37C C38C 1.450(10) . ?
C37C H37E 0.9900 . ?
C37C H37F 0.9900 . ?
C38C H38G 0.9800 . ?
C38C H38H 0.9800 . ?
C38C H38I 0.9800 . ?
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
C3 N1 C1 O1 -179.17(12) . . . . ?
C31C N1 C1 O1 11.6(2) . . . . ?
C31 N1 C1 O1 11.6(2) . . . . ?
C31B N1 C1 O1 11.6(2) . . . . ?
C3 N1 C1 C2 -0.27(14) . . . 2_675 ?
C31C N1 C1 C2 -169.51(13) . . . 2_675 ?
C31 N1 C1 C2 -169.51(13) . . . 2_675 ?
C31B N1 C1 C2 -169.51(13) . . . 2_675 ?
C2 C2 C3 N1 1.13(17) 2_675 . . . ?
C1 C2 C3 N1 179.07(16) 2_675 . . . ?
C2 C2 C3 C4 -175.38(13) 2_675 . . . ?
C1 C2 C3 C4 2.6(3) 2_675 . . . ?
C1 N1 C3 C2 -0.53(15) . . . . ?
C31C N1 C3 C2 167.47(14) . . . . ?
C31 N1 C3 C2 167.47(14) . . . . ?
C31B N1 C3 C2 167.47(14) . . . . ?
C1 N1 C3 C4 176.11(12) . . . . ?
C31C N1 C3 C4 -15.9(2) . . . . ?
C31 N1 C3 C4 -15.9(2) . . . . ?
C31B N1 C3 C4 -15.9(2) . . . . ?
C2 C3 C4 C9 141.98(14) . . . . ?
N1 C3 C4 C9 -34.0(2) . . . . ?
C2 C3 C4 C5 -33.67(19) . . . . ?
N1 C3 C4 C5 150.40(13) . . . . ?
C7 C6 C5 C4 0.6(2) . . . . ?
C9 C4 C5 C6 1.93(19) . . . . ?
C3 C4 C5 C6 177.80(12) . . . . ?
C5 C6 C7 C8 -2.29(19) . . . . ?
C5 C6 C7 C10 175.20(12) . . . . ?
C5 C4 C9 C8 -2.7(2) . . . . ?
C3 C4 C9 C8 -178.33(12) . . . . ?
C4 C9 C8 C7 0.9(2) . . . . ?
C6 C7 C8 C9 1.6(2) . . . . ?
C10 C7 C8 C9 -175.96(12) . . . . ?
C8 C7 C10 C15 -30.19(18) . . . . ?
C6 C7 C10 C15 152.39(12) . . . . ?
C8 C7 C10 C11 145.24(13) . . . . ?
C6 C7 C10 C11 -32.18(18) . . . . ?
C15 C10 C11 C12 1.92(18) . . . . ?
C7 C10 C11 C12 -173.63(11) . . . . ?
C10 C11 C12 C13 0.01(18) . . . . ?
C10 C11 C12 C16 177.59(11) . . . . ?
C11 C12 C13 O2 173.70(11) . . . . ?
C16 C12 C13 O2 -3.85(17) . . . . ?
C11 C12 C13 C14 -1.41(18) . . . . ?
C16 C12 C13 C14 -178.97(11) . . . . ?
O2 C13 C14 C15 -174.13(11) . . . . ?
C12 C13 C14 C15 0.82(18) . . . . ?
O2 C13 C14 C20 4.23(18) . . . . ?
C12 C13 C14 C20 179.17(11) . . . . ?
C11 C10 C15 C14 -2.57(18) . . . . ?
C7 C10 C15 C14 172.95(11) . . . . ?
C13 C14 C15 C10 1.22(18) . . . . ?
C20 C14 C15 C10 -177.17(11) . . . . ?
C11 C12 C16 C17 -113.89(13) . . . . ?
C13 C12 C16 C17 63.59(15) . . . . ?
C11 C12 C16 C18 5.54(17) . . . . ?
C13 C12 C16 C18 -176.99(12) . . . . ?
C11 C12 C16 C19 124.02(13) . . . . ?
C13 C12 C16 C19 -58.50(16) . . . . ?
C15 C14 C20 C21 3.87(17) . . . . ?
C13 C14 C20 C21 -174.43(12) . . . . ?
C15 C14 C20 C23 -115.10(13) . . . . ?
C13 C14 C20 C23 66.59(16) . . . . ?
C15 C14 C20 C22 122.60(14) . . . . ?
C13 C14 C20 C22 -55.71(17) . . . . ?
C3 N1 C31 C32 -68.5(2) . . . . ?
C1 N1 C31 C32 98.66(19) . . . . ?
N1 C31 C32 C37 -68.1(6) . . . . ?
N1 C31 C32 C33 172.2(2) . . . . ?
C37 C32 C33 C34 172.9(5) . . . . ?
C31 C32 C33 C34 -64.6(3) . . . . ?
C32 C33 C34 C35 -167.6(3) . . . . ?
C33 C34 C35 C36 -67.3(4) . . . . ?
C33 C32 C37 C38 -64.6(12) . . . . ?
C31 C32 C37 C38 178.1(10) . . . . ?
C3 N1 C31B C32B -92.1(6) . . . . ?
C1 N1 C31B C32B 75.1(6) . . . . ?
N1 C31B C32B C37B -23.8(18) . . . . ?
N1 C31B C32B C33B -173.1(6) . . . . ?
C37B C32B C33B C34B 136.9(14) . . . . ?
C31B C32B C33B C34B -72.8(12) . . . . ?
C32B C33B C34B C35B 172.4(8) . . . . ?
C33B C34B C35B C36B -178.3(8) . . . . ?
C31B C32B C37B C38B 163(2) . . . . ?
C33B C32B C37B C38B -52(3) . . . . ?
C3 N1 C31C C32C -35.5(5) . . . . ?
C1 N1 C31C C32C 131.7(4) . . . . ?
N1 C31C C32C C37C 176.5(3) . . . . ?
N1 C31C C32C C33C -57.5(5) . . . . ?
C31C C32C C33C C34C -71.5(6) . . . . ?
C37C C32C C33C C34C 52.5(8) . . . . ?
C32C C33C C34C C35C 171.8(6) . . . . ?
C33C C34C C35C C36C 61.9(8) . . . . ?
C31C C32C C37C C38C -179.0(7) . . . . ?
C33C C32C C37C C38C 63.8(8) . . . . ?
