#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:34:37 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158140.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_7158140
loop_
_publ_author_name
'Zhan, Shao-Cong'
'Fang, Ren-Jie'
'Sun, Jing'
'Yan, Chao-Guo'
_publ_section_title
;
 Diastereoselective synthesis of spiro[carbazole-3,5'-pyrimidines] and
 spiro[carbazole-3,1'-cyclohexanes] via four-component reaction.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6322
_journal_page_last               6327
_journal_paper_doi               10.1039/d1ob01113h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C34 H33 N3 O5'
_chemical_formula_sum            'C34 H33 N3 O5'
_chemical_formula_weight         563.63
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.226(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.6658(12)
_cell_length_b                   12.4540(8)
_cell_length_c                   26.766(2)
_cell_measurement_reflns_used    5433
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.52
_cell_measurement_theta_min      2.32
_cell_volume                     5864.3(7)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1698
_diffrn_reflns_av_unetI/netI     0.1867
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            59155
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.528
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             2384
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     767
_refine_ls_number_reflns         11530
_refine_ls_number_restraints     396
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.2613
_refine_ls_R_factor_gt           0.1063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0862P)²+18.8524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2190
_refine_ls_wR_factor_ref         0.2918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4692
_reflns_number_total             11530
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01113h2.cif
_cod_data_source_block           2aa
_cod_depositor_comments
'Adding full bibliography for 7158139--7158148.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158140
_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   0.978
_shelx_estimated_absorpt_t_max   0.985
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
C1 C 0.4509(3) 0.3611(5) 0.1435(2) 0.0457(7) Uani 1 1 d . U . . .
C2 C 0.5296(3) 0.3573(5) 0.1448(2) 0.0479(7) Uani 1 1 d . U . . .
H2 H 0.5586 0.3224 0.1706 0.057 Uiso 1 1 calc R U . . .
C3 C 0.5629(4) 0.4063(5) 0.1069(2) 0.0496(7) Uani 1 1 d . U . . .
H3 H 0.6156 0.4056 0.1072 0.059 Uiso 1 1 calc R U . . .
C4 C 0.5201(3) 0.4569(5) 0.0682(2) 0.0496(7) Uani 1 1 d . U . . .
H4 H 0.5448 0.4914 0.0435 0.060 Uiso 1 1 calc R U . . .
C5 C 0.4413(3) 0.4578(5) 0.0652(2) 0.0476(7) Uani 1 1 d . U . . .
H5 H 0.4131 0.4899 0.0382 0.057 Uiso 1 1 calc R U . . .
C6 C 0.4053(3) 0.4092(5) 0.1036(2) 0.0446(6) Uani 1 1 d . U . . .
C7 C 0.3279(3) 0.3975(5) 0.1144(2) 0.0419(5) Uani 1 1 d . U . . .
C8 C 0.3287(3) 0.3473(5) 0.1593(2) 0.0405(6) Uani 1 1 d . U . . .
C9 C 0.2622(3) 0.3216(5) 0.1878(2) 0.0409(6) Uani 1 1 d . U . . .
H9 H 0.2514 0.2445 0.1852 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2795(3) 0.3519(5) 0.2427(2) 0.0415(8) Uani 1 1 d . U . . .
C11 C 0.3374(5) 0.2903(7) 0.3216(3) 0.0825(19) Uani 1 1 d . U . . .
H11A H 0.2932 0.3040 0.3396 0.099 Uiso 1 1 calc R U . . .
H11B H 0.3716 0.3512 0.3260 0.099 Uiso 1 1 calc R U . . .
C12 C 0.3766(5) 0.1895(7) 0.3401(3) 0.0848(19) Uani 1 1 d . U . . .
H12A H 0.3424 0.1299 0.3346 0.127 Uiso 1 1 calc R U . . .
H12B H 0.3918 0.1962 0.3753 0.127 Uiso 1 1 calc R U . . .
H12C H 0.4206 0.1779 0.3223 0.127 Uiso 1 1 calc R U . . .
C13 C 0.2562(3) 0.4390(5) 0.0853(2) 0.0421(5) Uani 1 1 d . U . . .
H13 H 0.2534 0.5162 0.0918 0.050 Uiso 1 1 calc R U . . .
C14 C 0.2554(3) 0.4250(5) 0.0286(2) 0.0461(6) Uani 1 1 d . U . . .
C15 C 0.2793(3) 0.3284(5) 0.0092(2) 0.0490(7) Uani 1 1 d . U . . .
H15 H 0.3002 0.2762 0.0311 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2726(3) 0.3079(5) -0.0417(2) 0.0517(7) Uani 1 1 d . U . . .
H16 H 0.2868 0.2417 -0.0539 0.062 Uiso 1 1 calc R U . . .
C17 C 0.2446(4) 0.3877(5) -0.0743(3) 0.0526(7) Uani 1 1 d . U . . .
H17 H 0.2386 0.3747 -0.1086 0.063 Uiso 1 1 calc R U . . .
C18 C 0.2256(3) 0.4855(5) -0.0560(2) 0.0512(7) Uani 1 1 d . U . . .
H18 H 0.2093 0.5394 -0.0785 0.061 Uiso 1 1 calc R U . . .
C19 C 0.2299(4) 0.5068(5) -0.0049(2) 0.0486(7) Uani 1 1 d . U . . .
C20 C 0.2092(4) 0.6178(5) 0.0107(2) 0.0520(11) Uani 1 1 d . U . . .
H20A H 0.2455 0.6422 0.0371 0.078 Uiso 1 1 calc R U . . .
H20B H 0.1594 0.6168 0.0224 0.078 Uiso 1 1 calc R U . . .
H20C H 0.2093 0.6654 -0.0175 0.078 Uiso 1 1 calc R U . . .
C21 C 0.1748(3) 0.2729(5) 0.0857(2) 0.0390(7) Uani 1 1 d . U . . .
C22 C 0.1078(4) 0.1434(5) 0.0287(3) 0.070(2) Uani 1 1 d . . . . .
H22A H 0.1000 0.0906 0.0538 0.104 Uiso 1 1 calc R U . . .
H22B H 0.1543 0.1282 0.0141 0.104 Uiso 1 1 calc R U . . .
H22C H 0.0661 0.1413 0.0031 0.104 Uiso 1 1 calc R U . . .
C23 C 0.0503(3) 0.3174(5) 0.0430(3) 0.0455(17) Uani 1 1 d . . . . .
C24 C -0.0170(4) 0.4816(6) 0.0643(3) 0.073(2) Uani 1 1 d . . . . .
H24A H -0.0340 0.4867 0.0973 0.110 Uiso 1 1 calc R U . . .
H24B H -0.0557 0.4480 0.0421 0.110 Uiso 1 1 calc R U . . .
H24C H -0.0069 0.5522 0.0522 0.110 Uiso 1 1 calc R U . . .
C25 C 0.1173(3) 0.4598(5) 0.0920(2) 0.0395(7) Uani 1 1 d . U . . .
C26 C 0.1846(3) 0.3858(5) 0.1060(2) 0.0401(5) Uani 1 1 d . U . . .
C27 C 0.1925(3) 0.3850(5) 0.1651(2) 0.0415(5) Uani 1 1 d . U . . .
H27 H 0.2007 0.4597 0.1757 0.050 Uiso 1 1 calc R U . . .
C28 C 0.1170(3) 0.3505(5) 0.1844(2) 0.0453(6) Uani 1 1 d . U . . .
C29 C 0.0910(3) 0.2464(5) 0.1762(2) 0.0469(7) Uani 1 1 d . U . . .
H29 H 0.1223 0.1966 0.1625 0.056 Uiso 1 1 calc R U . . .
C30 C 0.0202(3) 0.2146(5) 0.1879(2) 0.0494(7) Uani 1 1 d . U . . .
H30 H 0.0038 0.1445 0.1817 0.059 Uiso 1 1 calc R U . . .
C31 C -0.0262(4) 0.2875(5) 0.2088(2) 0.0509(7) Uani 1 1 d . U . . .
H31 H -0.0748 0.2675 0.2160 0.061 Uiso 1 1 calc R U . . .
C32 C -0.0006(3) 0.3892(5) 0.2190(2) 0.0504(7) Uani 1 1 d . U . . .
H32 H -0.0319 0.4369 0.2342 0.061 Uiso 1 1 calc R U . . .
C33 C 0.0702(3) 0.4242(5) 0.2075(2) 0.0485(7) Uani 1 1 d . U . . .
C34 C 0.0931(4) 0.5374(5) 0.2209(3) 0.0542(11) Uani 1 1 d . U . . .
H34A H 0.0981 0.5776 0.1907 0.081 Uiso 1 1 calc R U . . .
H34B H 0.1408 0.5370 0.2411 0.081 Uiso 1 1 calc R U . . .
H34C H 0.0550 0.5700 0.2393 0.081 Uiso 1 1 calc R U . . .
C35 C 0.1560(3) 0.8864(5) -0.0116(2) 0.0459(7) Uani 1 1 d . U . . .
C36 C 0.1266(4) 0.8853(5) -0.0615(2) 0.0483(7) Uani 1 1 d . U . . .
H36 H 0.0785 0.8583 -0.0711 0.058 Uiso 1 1 calc R U . . .
C37 C 0.1715(3) 0.9256(5) -0.0956(3) 0.0498(7) Uani 1 1 d . U . . .
H37 H 0.1529 0.9261 -0.1292 0.060 Uiso 1 1 calc R U . . .
C38 C 0.2436(3) 0.9658(5) -0.0826(2) 0.0494(7) Uani 1 1 d . U . . .
H38 H 0.2720 0.9931 -0.1072 0.059 Uiso 1 1 calc R U . . .
C39 C 0.2733(4) 0.9655(5) -0.0331(2) 0.0472(7) Uani 1 1 d . U . . .
H39 H 0.3220 0.9917 -0.0243 0.057 Uiso 1 1 calc R U . . .
C40 C 0.2292(3) 0.9251(5) 0.0037(2) 0.0444(6) Uani 1 1 d . U . . .
C41 C 0.2407(3) 0.9119(5) 0.0572(2) 0.0413(5) Uani 1 1 d . U . . .
C42 C 0.1763(3) 0.8685(5) 0.0721(2) 0.0399(6) Uani 1 1 d . U . . .
C43 C 0.1608(3) 0.8429(5) 0.1250(2) 0.0397(6) Uani 1 1 d . U . . .
H43 H 0.1638 0.7650 0.1301 0.048 Uiso 1 1 calc R U . . .
C44 C 0.0820(3) 0.8817(5) 0.1347(2) 0.0403(8) Uani 1 1 d . U . . .
C45 C -0.0478(5) 0.8365(11) 0.1306(6) 0.169(4) Uani 1 1 d . U . . .
H45A H -0.0483 0.8994 0.1519 0.203 Uiso 1 1 calc R U . . .
H45B H -0.0732 0.8549 0.0981 0.203 Uiso 1 1 calc R U . . .
C46 C -0.0860(5) 0.7556(10) 0.1510(5) 0.172(4) Uani 1 1 d . U . . .
H46A H -0.1041 0.7060 0.1251 0.258 Uiso 1 1 calc R U . . .
H46B H -0.1284 0.7845 0.1666 0.258 Uiso 1 1 calc R U . . .
H46C H -0.0526 0.7189 0.1756 0.258 Uiso 1 1 calc R U . . .
C47 C 0.3085(3) 0.9445(5) 0.0921(2) 0.0414(5) Uani 1 1 d . U . . .
H47 H 0.3054 1.0225 0.0963 0.050 Uiso 1 1 calc R U . . .
C48 C 0.3852(3) 0.9212(5) 0.0727(2) 0.0457(6) Uani 1 1 d . U . . .
C49 C 0.3973(3) 0.8230(5) 0.0504(2) 0.0483(7) Uani 1 1 d . U . . .
H49 H 0.3571 0.7748 0.0454 0.058 Uiso 1 1 calc R U . . .
C50 C 0.4677(3) 0.7945(5) 0.0354(2) 0.0510(7) Uani 1 1 d . U . . .
H50 H 0.4747 0.7284 0.0203 0.061 Uiso 1 1 calc R U . . .
C51 C 0.5261(4) 0.8654(5) 0.0433(2) 0.0521(7) Uani 1 1 d . U . . .
H51 H 0.5742 0.8462 0.0349 0.063 Uiso 1 1 calc R U . . .
C52 C 0.5153(4) 0.9632(5) 0.0630(2) 0.0514(7) Uani 1 1 d . U . . .
H52 H 0.5559 1.0109 0.0670 0.062 Uiso 1 1 calc R U . . .
C53 C 0.4453(3) 0.9949(5) 0.0776(2) 0.0490(7) Uani 1 1 d . U . . .
C54 C 0.4373(4) 1.1093(5) 0.0953(3) 0.0542(11) Uani 1 1 d . U . . .
H54A H 0.4785 1.1517 0.0850 0.081 Uiso 1 1 calc R U . . .
H54B H 0.4385 1.1103 0.1313 0.081 Uiso 1 1 calc R U . . .
H54C H 0.3899 1.1384 0.0810 0.081 Uiso 1 1 calc R U . . .
C55 C 0.3279(3) 0.7763(5) 0.1450(2) 0.0377(7) Uani 1 1 d . U . . .
C56 C 0.4096(4) 0.6313(5) 0.1771(3) 0.075(3) Uani 1 1 d . . . . .
H56A H 0.3634 0.5906 0.1758 0.112 Uiso 1 1 calc R U . . .
H56B H 0.4404 0.6149 0.2075 0.112 Uiso 1 1 calc R U . . .
H56C H 0.4369 0.6131 0.1488 0.112 Uiso 1 1 calc R U . . .
C57 C 0.4367(3) 0.8143(5) 0.2061(2) 0.0433(16) Uani 1 1 d . . . . .
C58 C 0.4679(4) 0.9945(5) 0.2364(3) 0.069(2) Uani 1 1 d . . . . .
H58A H 0.4589 0.9875 0.2711 0.103 Uiso 1 1 calc R U . . .
H58B H 0.4579 1.0671 0.2256 0.103 Uiso 1 1 calc R U . . .
H58C H 0.5199 0.9769 0.2323 0.103 Uiso 1 1 calc R U . . .
C59 C 0.3518(3) 0.9637(5) 0.1819(2) 0.0381(7) Uani 1 1 d . U . . .
C60 C 0.3028(3) 0.8928(4) 0.1456(2) 0.0388(5) Uani 1 1 d . U . . .
C61 C 0.2201(3) 0.8988(5) 0.1624(2) 0.0400(5) Uani 1 1 d . U . . .
H61 H 0.2064 0.9751 0.1622 0.048 Uiso 1 1 calc R U . . .
C62 C 0.2199(3) 0.8609(5) 0.2167(2) 0.0433(6) Uani 1 1 d . U . . .
C63 C 0.2326(3) 0.7524(5) 0.2284(2) 0.0455(7) Uani 1 1 d . U . . .
H63 H 0.2337 0.7031 0.2024 0.055 Uiso 1 1 calc R U . . .
C64 C 0.2436(3) 0.7160(5) 0.2775(2) 0.0481(7) Uani 1 1 d . U . . .
H64 H 0.2525 0.6436 0.2842 0.058 Uiso 1 1 calc R U . . .
C65 C 0.2412(3) 0.7885(5) 0.3160(3) 0.0493(7) Uani 1 1 d . U . . .
H65 H 0.2506 0.7662 0.3492 0.059 Uiso 1 1 calc R U . . .
C66 C 0.2250(3) 0.8933(5) 0.3053(2) 0.0485(7) Uani 1 1 d . U . . .
H66 H 0.2220 0.9409 0.3318 0.058 Uiso 1 1 calc R U . . .
C67 C 0.2125(3) 0.9327(5) 0.2566(2) 0.0461(7) Uani 1 1 d . U . . .
C68 C 0.1921(4) 1.0481(5) 0.2488(2) 0.0499(11) Uani 1 1 d . U . . .
H68A H 0.1832 1.0800 0.2804 0.075 Uiso 1 1 calc R U . . .
H68B H 0.1469 1.0537 0.2262 0.075 Uiso 1 1 calc R U . . .
H68C H 0.2330 1.0850 0.2349 0.075 Uiso 1 1 calc R U . . .
N1 N 0.4030(2) 0.3240(4) 0.17741(18) 0.0395(12) Uani 1 1 d . . . . .
H1 H 0.4168 0.2918 0.2052 0.047 Uiso 1 1 calc R U . . .
N2 N 0.1124(3) 0.2515(4) 0.05192(18) 0.0404(13) Uani 1 1 d . . . . .
N3 N 0.0535(2) 0.4164(4) 0.06641(19) 0.0418(13) Uani 1 1 d . . . . .
N4 N 0.1239(2) 0.8536(4) 0.03109(18) 0.0394(13) Uani 1 1 d . . . . .
H4A H 0.0788 0.8282 0.0320 0.047 Uiso 1 1 calc R U . . .
N5 N 0.3917(3) 0.7466(4) 0.17570(18) 0.0399(13) Uani 1 1 d . . . . .
N6 N 0.4173(3) 0.9212(4) 0.20589(18) 0.0401(13) Uani 1 1 d . . . . .
O1 O 0.2660(4) 0.4357(4) 0.2608(2) 0.097(2) Uani 1 1 d . . . . .
O2 O 0.3148(3) 0.2720(4) 0.26802(16) 0.0565(12) Uani 1 1 d . . . . .
O3 O 0.2202(2) 0.2023(3) 0.09676(15) 0.0444(11) Uani 1 1 d . . . . .
O4 O -0.0051(3) 0.2905(4) 0.0164(2) 0.0763(17) Uani 1 1 d . . . . .
O5 O 0.1179(2) 0.5524(3) 0.10540(17) 0.0526(12) Uani 1 1 d . . . . .
O6 O 0.0672(3) 0.9696(4) 0.1470(2) 0.0841(17) Uani 1 1 d . . . . .
O7 O 0.0309(2) 0.8064(4) 0.1247(2) 0.0860(18) Uani 1 1 d . . . . .
O8 O 0.2925(2) 0.7096(3) 0.11976(15) 0.0402(10) Uani 1 1 d . . . . .
O9 O 0.4912(3) 0.7801(4) 0.23189(19) 0.0719(16) Uani 1 1 d . . . . .
O10 O 0.3362(2) 1.0573(3) 0.18793(15) 0.0462(11) 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
N1 C1 C2 130.4(6) . . ?
N1 C1 C6 107.3(5) . . ?
C2 C1 C6 122.3(6) . . ?
C3 C2 C1 117.8(6) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.4(6) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 121.7(6) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 118.4(6) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 118.3(5) . . ?
C5 C6 C7 134.4(6) . . ?
C1 C6 C7 107.2(5) . . ?
C8 C7 C6 107.0(5) . . ?
C8 C7 C13 123.7(5) . . ?
C6 C7 C13 129.2(6) . . ?
C7 C8 N1 109.9(5) . . ?
C7 C8 C9 127.3(5) . . ?
N1 C8 C9 122.8(5) . . ?
C8 C9 C10 109.9(5) . . ?
C8 C9 C27 109.2(5) . . ?
C10 C9 C27 109.6(5) . . ?
C8 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
C27 C9 H9 109.3 . . ?
O1 C10 O2 123.7(6) . . ?
O1 C10 C9 125.7(6) . . ?
O2 C10 C9 110.6(5) . . ?
O2 C11 C12 105.7(6) . . ?
O2 C11 H11A 110.6 . . ?
C12 C11 H11A 110.6 . . ?
O2 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C14 113.8(5) . . ?
C7 C13 C26 109.7(5) . . ?
C14 C13 C26 111.6(5) . . ?
C7 C13 H13 107.2 . . ?
C14 C13 H13 107.2 . . ?
C26 C13 H13 107.2 . . ?
C15 C14 C19 118.7(6) . . ?
C15 C14 C13 119.6(6) . . ?
C19 C14 C13 121.7(6) . . ?
C16 C15 C14 121.7(6) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 118.8(6) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 120.1(6) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 122.0(6) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C14 118.4(6) . . ?
C18 C19 C20 117.2(6) . . ?
C14 C19 C20 124.3(6) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 N2 119.4(5) . . ?
O3 C21 C26 122.5(5) . . ?
N2 C21 C26 118.1(5) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 N2 122.0(6) . . ?
O4 C23 N3 120.9(6) . . ?
N2 C23 N3 117.1(5) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 N3 120.6(5) . . ?
O5 C25 C26 121.2(5) . . ?
N3 C25 C26 118.1(5) . . ?
C21 C26 C25 114.4(5) . . ?
C21 C26 C13 109.5(5) . . ?
C25 C26 C13 107.1(5) . . ?
C21 C26 C27 110.5(5) . . ?
C25 C26 C27 104.2(5) . . ?
C13 C26 C27 110.9(5) . . ?
C28 C27 C9 114.4(5) . . ?
C28 C27 C26 109.8(5) . . ?
C9 C27 C26 113.1(5) . . ?
C28 C27 H27 106.3 . . ?
C9 C27 H27 106.3 . . ?
C26 C27 H27 106.3 . . ?
C29 C28 C33 118.5(6) . . ?
C29 C28 C27 119.6(5) . . ?
C33 C28 C27 121.7(5) . . ?
C30 C29 C28 121.9(6) . . ?
C30 C29 H29 119.0 . . ?
C28 C29 H29 119.0 . . ?
C31 C30 C29 119.4(6) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C32 C31 C30 119.7(6) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C33 122.5(6) . . ?
C31 C32 H32 118.7 . . ?
C33 C32 H32 118.7 . . ?
C32 C33 C28 117.9(6) . . ?
C32 C33 C34 118.1(6) . . ?
C28 C33 C34 123.9(6) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N4 C35 C36 130.3(6) . . ?
N4 C35 C40 107.2(5) . . ?
C36 C35 C40 122.5(6) . . ?
C37 C36 C35 117.0(6) . . ?
C37 C36 H36 121.5 . . ?
C35 C36 H36 121.5 . . ?
C36 C37 C38 123.0(6) . . ?
C36 C37 H37 118.5 . . ?
C38 C37 H37 118.5 . . ?
C39 C38 C37 120.1(6) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C38 C39 C40 119.2(6) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
C39 C40 C35 118.2(6) . . ?
C39 C40 C41 134.6(6) . . ?
C35 C40 C41 107.2(5) . . ?
C42 C41 C40 107.0(5) . . ?
C42 C41 C47 124.6(6) . . ?
C40 C41 C47 128.3(5) . . ?
C41 C42 N4 109.9(5) . . ?
C41 C42 C43 126.5(5) . . ?
N4 C42 C43 123.6(5) . . ?
C42 C43 C44 110.1(5) . . ?
C42 C43 C61 110.1(5) . . ?
C44 C43 C61 108.8(5) . . ?
C42 C43 H43 109.3 . . ?
C44 C43 H43 109.3 . . ?
C61 C43 H43 109.3 . . ?
O6 C44 O7 123.7(6) . . ?
O6 C44 C43 125.0(6) . . ?
O7 C44 C43 111.2(5) . . ?
C46 C45 O7 111.5(10) . . ?
C46 C45 H45A 109.3 . . ?
O7 C45 H45A 109.3 . . ?
C46 C45 H45B 109.3 . . ?
O7 C45 H45B 109.3 . . ?
H45A C45 H45B 108.0 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C41 C47 C48 114.8(5) . . ?
C41 C47 C60 109.8(5) . . ?
C48 C47 C60 111.3(5) . . ?
C41 C47 H47 106.8 . . ?
C48 C47 H47 106.8 . . ?
C60 C47 H47 106.8 . . ?
C49 C48 C53 118.3(6) . . ?
C49 C48 C47 119.5(5) . . ?
C53 C48 C47 122.2(6) . . ?
C50 C49 C48 121.9(6) . . ?
C50 C49 H49 119.1 . . ?
C48 C49 H49 119.1 . . ?
C51 C50 C49 118.4(6) . . ?
C51 C50 H50 120.8 . . ?
C49 C50 H50 120.8 . . ?
C52 C51 C50 121.0(6) . . ?
C52 C51 H51 119.5 . . ?
C50 C51 H51 119.5 . . ?
C51 C52 C53 121.9(6) . . ?
C51 C52 H52 119.1 . . ?
C53 C52 H52 119.1 . . ?
C52 C53 C48 118.3(6) . . ?
C52 C53 C54 117.8(6) . . ?
C48 C53 C54 123.8(6) . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O8 C55 N5 120.0(5) . . ?
O8 C55 C60 121.7(5) . . ?
N5 C55 C60 118.2(5) . . ?
N5 C56 H56A 109.5 . . ?
N5 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
N5 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
O9 C57 N5 120.6(6) . . ?
O9 C57 N6 121.9(5) . . ?
N5 C57 N6 117.5(5) . . ?
N6 C58 H58A 109.5 . . ?
N6 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
N6 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
O10 C59 N6 120.0(5) . . ?
O10 C59 C60 121.3(5) . . ?
N6 C59 C60 118.6(5) . . ?
C55 C60 C59 114.3(5) . . ?
C55 C60 C61 109.3(5) . . ?
C59 C60 C61 106.2(5) . . ?
C55 C60 C47 109.7(5) . . ?
C59 C60 C47 105.2(5) . . ?
C61 C60 C47 112.2(4) . . ?
C62 C61 C43 114.6(5) . . ?
C62 C61 C60 109.9(5) . . ?
C43 C61 C60 112.8(5) . . ?
C62 C61 H61 106.3 . . ?
C43 C61 H61 106.3 . . ?
C60 C61 H61 106.3 . . ?
C63 C62 C67 117.8(6) . . ?
C63 C62 C61 119.8(6) . . ?
C67 C62 C61 122.2(5) . . ?
C64 C63 C62 122.3(6) . . ?
C64 C63 H63 118.9 . . ?
C62 C63 H63 118.9 . . ?
C65 C64 C63 119.0(6) . . ?
C65 C64 H64 120.5 . . ?
C63 C64 H64 120.5 . . ?
C66 C65 C64 119.4(6) . . ?
C66 C65 H65 120.3 . . ?
C64 C65 H65 120.3 . . ?
C65 C66 C67 123.2(6) . . ?
C65 C66 H66 118.4 . . ?
C67 C66 H66 118.4 . . ?
C66 C67 C62 118.0(6) . . ?
C66 C67 C68 119.0(6) . . ?
C62 C67 C68 123.0(6) . . ?
C67 C68 H68A 109.5 . . ?
C67 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C67 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C1 N1 C8 108.6(5) . . ?
C1 N1 H1 125.7 . . ?
C8 N1 H1 125.7 . . ?
C23 N2 C21 125.0(5) . . ?
C23 N2 C22 117.3(5) . . ?
C21 N2 C22 117.3(5) . . ?
C25 N3 C23 125.0(5) . . ?
C25 N3 C24 116.8(5) . . ?
C23 N3 C24 118.1(5) . . ?
C35 N4 C42 108.7(5) . . ?
C35 N4 H4A 125.6 . . ?
C42 N4 H4A 125.6 . . ?
C57 N5 C55 125.7(5) . . ?
C57 N5 C56 118.2(5) . . ?
C55 N5 C56 116.0(5) . . ?
C57 N6 C59 125.0(5) . . ?
C57 N6 C58 117.4(5) . . ?
C59 N6 C58 117.5(5) . . ?
C10 O2 C11 117.1(5) . . ?
C44 O7 C45 115.9(7) . . ?
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 N1 1.376(7) . ?
C1 C2 1.388(8) . ?
C1 C6 1.411(8) . ?
C2 C3 1.361(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.430(8) . ?
C7 C8 1.355(8) . ?
C7 C13 1.516(8) . ?
C8 N1 1.387(7) . ?
C8 C9 1.492(8) . ?
C9 C10 1.522(8) . ?
C9 C27 1.539(8) . ?
C9 H9 0.9800 . ?
C10 O1 1.184(7) . ?
C10 O2 1.327(7) . ?
C11 O2 1.471(8) . ?
C11 C12 1.495(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.526(8) . ?
C13 C26 1.573(8) . ?
C13 H13 0.9800 . ?
C14 C15 1.390(8) . ?
C14 C19 1.404(8) . ?
C15 C16 1.382(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.499(8) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O3 1.209(6) . ?
C21 N2 1.387(7) . ?
C21 C26 1.511(8) . ?
C22 N2 1.483(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O4 1.206(7) . ?
C23 N2 1.373(7) . ?
C23 N3 1.381(7) . ?
C24 N3 1.483(7) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O5 1.208(7) . ?
C25 N3 1.375(7) . ?
C25 C26 1.523(8) . ?
C26 C27 1.577(8) . ?
C27 C28 1.533(8) . ?
C27 H27 0.9800 . ?
C28 C29 1.387(8) . ?
C28 C33 1.415(8) . ?
C29 C30 1.375(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.375(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.364(8) . ?
C31 H31 0.9300 . ?
C32 C33 1.385(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.501(8) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 N4 1.382(8) . ?
C35 C36 1.388(8) . ?
C35 C40 1.405(8) . ?
C36 C37 1.358(8) . ?
C36 H36 0.9300 . ?
C37 C38 1.383(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.379(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.405(8) . ?
C39 H39 0.9300 . ?
C40 C41 1.436(8) . ?
C41 C42 1.352(8) . ?
C41 C47 1.505(8) . ?
C42 N4 1.382(7) . ?
C42 C43 1.501(8) . ?
C43 C44 1.519(8) . ?
C43 C61 1.548(8) . ?
C43 H43 0.9800 . ?
C44 O6 1.179(7) . ?
C44 O7 1.311(7) . ?
C45 C46 1.355(14) . ?
C45 O7 1.462(10) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 C48 1.523(8) . ?
C47 C60 1.583(8) . ?
C47 H47 0.9800 . ?
C48 C49 1.386(8) . ?
C48 C53 1.399(8) . ?
C49 C50 1.386(8) . ?
C49 H49 0.9300 . ?
C50 C51 1.360(8) . ?
C50 H50 0.9300 . ?
C51 C52 1.348(8) . ?
C51 H51 0.9300 . ?
C52 C53 1.388(8) . ?
C52 H52 0.9300 . ?
C53 C54 1.512(9) . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C55 O8 1.209(6) . ?
C55 N5 1.382(7) . ?
C55 C60 1.518(8) . ?
C56 N5 1.471(7) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C57 O9 1.210(7) . ?
C57 N5 1.374(7) . ?
C57 N6 1.374(7) . ?
C58 N6 1.472(7) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 O10 1.212(6) . ?
C59 N6 1.376(7) . ?
C59 C60 1.524(8) . ?
C60 C61 1.569(8) . ?
C61 C62 1.530(8) . ?
C61 H61 0.9800 . ?
C62 C63 1.400(8) . ?
C62 C67 1.407(8) . ?
C63 C64 1.386(8) . ?
C63 H63 0.9300 . ?
C64 C65 1.375(8) . ?
C64 H64 0.9300 . ?
C65 C66 1.361(8) . ?
C65 H65 0.9300 . ?
C66 C67 1.392(8) . ?
C66 H66 0.9300 . ?
C67 C68 1.492(8) . ?
C68 H68A 0.9600 . ?
C68 H68B 0.9600 . ?
C68 H68C 0.9600 . ?
N1 H1 0.8600 . ?
N4 H4A 0.8600 . ?
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
N4 H4A O4 0.86 2.29 2.959(6) 134.6 3_565
N1 H1 O9 0.86 2.24 2.976(6) 144.1 2_645
N1 H1 O2 0.86 2.59 3.069(6) 116.6 .
