#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:15:20 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268901 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/08/7060852.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_7060852
loop_
_publ_author_name
'Zhan, Shao-Cong'
'Fang, Ren-Jie'
'Yang, Ren-Yin'
'Zhao, Ru-Fang'
'Wang, Yang'
'Sun, Jing'
'Yan, Chao-Guo'
_publ_section_title
;
 DDQ dehydrogenative Diels--Alder reaction for the synthesis of
 functionalized spiro[carbazole-1,3′-indolines] and
 spiro[carbazole-1,5′-pyrimidines]
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15423
_journal_page_last               15428
_journal_paper_doi               10.1039/D1NJ02836G
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C49 H37 Cl N2 O4'
_chemical_formula_sum            'C49 H37 Cl N2 O4'
_chemical_formula_weight         753.25
_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
;
2021-04-14 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                99.021(2)
_cell_angle_beta                 99.217(3)
_cell_angle_gamma                110.717(3)
_cell_formula_units_Z            2
_cell_length_a                   12.3059(11)
_cell_length_b                   12.9944(10)
_cell_length_c                   13.5855(11)
_cell_measurement_reflns_used    5290
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.42
_cell_measurement_theta_min      2.49
_cell_volume                     1951.4(3)
_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      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.1226
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27540
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.960
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         7613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1978
_refine_ls_R_factor_gt           0.0749
_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)+(0.0897P)²+0.4700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.2031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3622
_reflns_number_total             7613
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj02836g2.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 7060849--7060852.cif.'
_cod_database_code               7060852
_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   0.963
_shelx_estimated_absorpt_t_max   0.971
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
C1 C 0.0113(3) 0.1205(3) 0.6035(3) 0.0640(10) Uani 1 1 d . . . . .
H1A H 0.0692 0.1115 0.5670 0.096 Uiso 1 1 calc R U . . .
H1B H -0.0578 0.1158 0.5557 0.096 Uiso 1 1 calc R U . . .
H1C H -0.0116 0.0617 0.6401 0.096 Uiso 1 1 calc R U . . .
C2 C 0.0288(3) 0.2510(3) 0.7663(2) 0.0495(9) Uani 1 1 d . . . . .
C3 C -0.0656(4) 0.1825(4) 0.8006(3) 0.0753(12) Uani 1 1 d . . . . .
H3 H -0.1169 0.1112 0.7613 0.090 Uiso 1 1 calc R U . . .
C4 C -0.0803(4) 0.2241(4) 0.8946(3) 0.0893(14) Uani 1 1 d . . . . .
H4 H -0.1421 0.1794 0.9197 0.107 Uiso 1 1 calc R U . . .
C5 C -0.0064(4) 0.3298(4) 0.9526(3) 0.0792(13) Uani 1 1 d . . . . .
H5 H -0.0195 0.3549 1.0158 0.095 Uiso 1 1 calc R U . . .
C6 C 0.0866(3) 0.3995(3) 0.9195(2) 0.0588(10) Uani 1 1 d . . . . .
H6 H 0.1353 0.4713 0.9593 0.071 Uiso 1 1 calc R U . . .
C7 C 0.1068(3) 0.3599(3) 0.8239(2) 0.0463(8) Uani 1 1 d . . . . .
C8 C 0.1902(3) 0.4053(2) 0.7633(2) 0.0398(8) Uani 1 1 d . . . . .
C9 C 0.1578(3) 0.3241(2) 0.6742(2) 0.0390(8) Uani 1 1 d . . . . .
C10 C 0.3776(3) 0.5755(3) 0.9730(2) 0.0508(9) Uani 1 1 d . . . . .
H10 H 0.3905 0.5090 0.9716 0.061 Uiso 1 1 calc R U . . .
C11 C 0.4131(3) 0.6540(3) 1.0635(3) 0.0599(10) Uani 1 1 d . . . . .
H11 H 0.4532 0.6429 1.1224 0.072 Uiso 1 1 calc R U . . .
C12 C 0.3890(4) 0.7495(3) 1.0664(3) 0.0657(11) Uani 1 1 d . . . . .
C13 C 0.3316(4) 0.7675(3) 0.9795(3) 0.0707(12) Uani 1 1 d . . . . .
H13 H 0.3144 0.8319 0.9822 0.085 Uiso 1 1 calc R U . . .
C14 C 0.3002(3) 0.6896(3) 0.8890(2) 0.0561(10) Uani 1 1 d . . . . .
H14 H 0.2626 0.7024 0.8299 0.067 Uiso 1 1 calc R U . . .
C15 C 0.3227(3) 0.5925(3) 0.8833(2) 0.0418(8) Uani 1 1 d . . . . .
C16 C 0.2908(3) 0.5125(2) 0.7823(2) 0.0421(8) Uani 1 1 d . . . . .
C17 C 0.3476(3) 0.5400(2) 0.7069(2) 0.0465(9) Uani 1 1 d . . . . .
C18 C 0.4412(4) 0.6503(3) 0.7099(3) 0.0624(11) Uani 1 1 d . . . . .
C19 C 0.5336(3) 0.7222(3) 0.8014(3) 0.0550(9) Uani 1 1 d . . . . .
C20 C 0.5662(4) 0.8392(3) 0.8186(3) 0.0701(11) Uani 1 1 d . . . . .
H20 H 0.5288 0.8691 0.7726 0.084 Uiso 1 1 calc R U . . .
C21 C 0.6514(5) 0.9090(3) 0.9014(4) 0.0962(15) Uani 1 1 d . . . . .
H21 H 0.6735 0.9868 0.9112 0.115 Uiso 1 1 calc R U . . .
C22 C 0.7063(4) 0.8659(4) 0.9721(4) 0.1005(16) Uani 1 1 d . . . . .
C23 C 0.8241(8) 0.9013(6) 1.1419(7) 0.246(6) Uani 1 1 d . . . . .
H23A H 0.7566 0.8480 1.1584 0.369 Uiso 1 1 calc R U . . .
H23B H 0.8679 0.9625 1.2008 0.369 Uiso 1 1 calc R U . . .
H23C H 0.8750 0.8644 1.1220 0.369 Uiso 1 1 calc R U . . .
C24 C 0.6821(4) 0.7541(4) 0.9541(4) 0.0917(15) Uani 1 1 d . . . . .
H24 H 0.7239 0.7255 0.9981 0.110 Uiso 1 1 calc R U . . .
C25 C 0.5942(4) 0.6824(3) 0.8691(3) 0.0702(11) Uani 1 1 d . . . . .
H25 H 0.5759 0.6050 0.8578 0.084 Uiso 1 1 calc R U . . .
C26 C 0.3507(4) -0.0281(4) 0.4339(3) 0.0738(12) Uani 1 1 d . . . . .
H26 H 0.3763 -0.0073 0.3765 0.089 Uiso 1 1 calc R U . . .
C27 C 0.3001(5) -0.1416(4) 0.4354(5) 0.0989(16) Uani 1 1 d . . . . .
H27 H 0.2907 -0.1965 0.3782 0.119 Uiso 1 1 calc R U . . .
C28 C 0.2646(5) -0.1732(4) 0.5184(5) 0.1073(18) Uani 1 1 d . . . . .
H28 H 0.2324 -0.2495 0.5190 0.129 Uiso 1 1 calc R U . . .
C29 C 0.2756(5) -0.0944(4) 0.6007(4) 0.1037(16) Uani 1 1 d . . . . .
H29 H 0.2507 -0.1161 0.6580 0.124 Uiso 1 1 calc R U . . .
C30 C 0.3243(4) 0.0200(3) 0.5998(3) 0.0738(12) Uani 1 1 d . . . . .
H30 H 0.3304 0.0740 0.6565 0.089 Uiso 1 1 calc R U . . .
C31 C 0.3629(3) 0.0537(3) 0.5174(3) 0.0509(9) Uani 1 1 d . . . . .
C32 C 0.4195(3) 0.1776(3) 0.5217(3) 0.0572(10) Uani 1 1 d . . . . .
H32A H 0.4869 0.2131 0.5806 0.069 Uiso 1 1 calc R U . . .
H32B H 0.4495 0.1879 0.4607 0.069 Uiso 1 1 calc R U . . .
C33 C 0.3296(3) 0.2920(2) 0.6182(3) 0.0425(8) Uani 1 1 d . . . . .
C34 C 0.2293(3) 0.3366(2) 0.5937(2) 0.0381(8) Uani 1 1 d . . . . .
C35 C 0.1710(3) 0.2748(2) 0.4828(2) 0.0406(8) Uani 1 1 d . . . . .
C36 C 0.0735(3) 0.2739(3) 0.4161(2) 0.0496(9) Uani 1 1 d . . . . .
H36 H 0.0243 0.3070 0.4403 0.060 Uiso 1 1 calc R U . . .
C37 C 0.0489(4) 0.2231(3) 0.3124(3) 0.0594(10) Uani 1 1 d . . . . .
C38 C -0.0530(4) 0.2294(4) 0.2371(3) 0.0923(15) Uani 1 1 d . . . . .
H38A H -0.0237 0.2585 0.1816 0.138 Uiso 1 1 calc R U . . .
H38B H -0.0849 0.2785 0.2714 0.138 Uiso 1 1 calc R U . . .
H38C H -0.1146 0.1551 0.2107 0.138 Uiso 1 1 calc R U . . .
C39 C 0.1223(4) 0.1735(3) 0.2796(3) 0.0697(12) Uani 1 1 d . . . . .
H39 H 0.1070 0.1409 0.2102 0.084 Uiso 1 1 calc R U . . .
C40 C 0.2190(4) 0.1701(3) 0.3463(3) 0.0604(10) Uani 1 1 d . . . . .
H40 H 0.2664 0.1340 0.3231 0.073 Uiso 1 1 calc R U . . .
C41 C 0.2417(3) 0.2225(3) 0.4482(2) 0.0448(8) Uani 1 1 d . . . . .
C42 C 0.2968(3) 0.4662(2) 0.5988(2) 0.0464(8) Uani 1 1 d . . . . .
H42 H 0.3642 0.4734 0.5667 0.056 Uiso 1 1 calc R U . . .
C43 C 0.2188(3) 0.5144(3) 0.5393(2) 0.0511(9) Uani 1 1 d . . . . .
C44 C 0.2238(3) 0.5249(3) 0.4313(2) 0.0494(9) Uani 1 1 d . . . . .
C45 C 0.3182(4) 0.5274(3) 0.3910(3) 0.0665(11) Uani 1 1 d . . . . .
H45 H 0.3839 0.5215 0.4306 0.080 Uiso 1 1 calc R U . . .
C46 C 0.3176(4) 0.5386(4) 0.2914(3) 0.0838(13) Uani 1 1 d . . . . .
H46 H 0.3834 0.5417 0.2646 0.101 Uiso 1 1 calc R U . . .
C47 C 0.2212(5) 0.5452(4) 0.2326(3) 0.0850(14) Uani 1 1 d . . . . .
H47 H 0.2198 0.5507 0.1650 0.102 Uiso 1 1 calc R U . . .
C48 C 0.1266(4) 0.5439(3) 0.2732(3) 0.0788(13) Uani 1 1 d . . . . .
H48 H 0.0608 0.5496 0.2336 0.095 Uiso 1 1 calc R U . . .
C49 C 0.1283(4) 0.5342(3) 0.3728(3) 0.0626(10) Uani 1 1 d . . . . .
H49 H 0.0638 0.5340 0.4004 0.075 Uiso 1 1 calc R U . . .
Cl1 Cl 0.43326(15) 0.84961(11) 1.18103(8) 0.1210(6) Uani 1 1 d . . . . .
N1 N 0.0629(2) 0.2302(2) 0.67561(19) 0.0463(7) Uani 1 1 d . . . . .
N2 N 0.3351(2) 0.2335(2) 0.5292(2) 0.0464(7) Uani 1 1 d . . . . .
O1 O 0.4411(3) 0.6817(2) 0.6291(2) 0.1074(12) Uani 1 1 d . . . . .
O2 O 0.7836(4) 0.9445(3) 1.0593(3) 0.169(2) Uani 1 1 d . . . . .
O3 O 0.3919(2) 0.3073(2) 0.70255(18) 0.0621(7) Uani 1 1 d . . . . .
O4 O 0.1487(2) 0.5422(2) 0.58001(18) 0.0704(8) 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'
Cl Cl 0.1484 0.1585 '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 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 129.2(3) . . ?
N1 C2 C7 108.5(3) . . ?
C3 C2 C7 122.3(3) . . ?
C4 C3 C2 117.5(4) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C5 C4 C3 121.9(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 118.8(4) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 118.0(3) . . ?
C2 C7 C8 106.3(3) . . ?
C6 C7 C8 135.7(3) . . ?
C9 C8 C7 106.3(3) . . ?
C9 C8 C16 122.0(3) . . ?
C7 C8 C16 131.8(3) . . ?
N1 C9 C8 110.9(3) . . ?
N1 C9 C34 126.4(3) . . ?
C8 C9 C34 122.3(3) . . ?
C11 C10 C15 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C15 C10 H10 119.2 . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 Cl1 119.5(3) . . ?
C13 C12 Cl1 119.6(3) . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 121.6(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C10 117.7(3) . . ?
C14 C15 C16 119.5(3) . . ?
C10 C15 C16 122.8(3) . . ?
C17 C16 C8 120.0(3) . . ?
C17 C16 C15 122.0(3) . . ?
C8 C16 C15 117.9(3) . . ?
C16 C17 C18 126.5(3) . . ?
C16 C17 C42 120.1(3) . . ?
C18 C17 C42 111.9(3) . . ?
O1 C18 C19 118.8(3) . . ?
O1 C18 C17 116.9(3) . . ?
C19 C18 C17 124.3(3) . . ?
C25 C19 C20 117.6(4) . . ?
C25 C19 C18 124.0(3) . . ?
C20 C19 C18 118.3(3) . . ?
C21 C20 C19 120.5(4) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C24 C22 C21 120.0(4) . . ?
C24 C22 O2 124.5(5) . . ?
C21 C22 O2 115.5(4) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 C25 119.1(4) . . ?
C22 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C19 C25 C24 121.9(4) . . ?
C19 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C31 C26 C27 119.9(4) . . ?
C31 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 120.9(5) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 119.9(5) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 119.9(5) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C31 C30 C29 121.0(4) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C26 118.3(4) . . ?
C30 C31 C32 119.1(3) . . ?
C26 C31 C32 122.6(3) . . ?
N2 C32 C31 112.2(3) . . ?
N2 C32 H32A 109.2 . . ?
C31 C32 H32A 109.2 . . ?
N2 C32 H32B 109.2 . . ?
C31 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
O3 C33 N2 126.4(3) . . ?
O3 C33 C34 126.1(3) . . ?
N2 C33 C34 107.6(3) . . ?
C9 C34 C35 120.8(3) . . ?
C9 C34 C33 110.0(2) . . ?
C35 C34 C33 101.7(2) . . ?
C9 C34 C42 109.2(2) . . ?
C35 C34 C42 108.9(2) . . ?
C33 C34 C42 105.0(2) . . ?
C41 C35 C36 120.3(3) . . ?
C41 C35 C34 108.0(3) . . ?
C36 C35 C34 131.4(3) . . ?
C35 C36 C37 119.9(3) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C39 C37 C36 118.6(3) . . ?
C39 C37 C38 121.2(4) . . ?
C36 C37 C38 120.1(4) . . ?
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 . . ?
C37 C39 C40 122.5(3) . . ?
C37 C39 H39 118.7 . . ?
C40 C39 H39 118.7 . . ?
C41 C40 C39 117.3(4) . . ?
C41 C40 H40 121.4 . . ?
C39 C40 H40 121.4 . . ?
C35 C41 C40 121.4(3) . . ?
C35 C41 N2 110.5(3) . . ?
C40 C41 N2 128.1(3) . . ?
C43 C42 C17 108.0(3) . . ?
C43 C42 C34 112.4(3) . . ?
C17 C42 C34 114.2(2) . . ?
C43 C42 H42 107.3 . . ?
C17 C42 H42 107.3 . . ?
C34 C42 H42 107.3 . . ?
O4 C43 C44 120.0(3) . . ?
O4 C43 C42 118.6(3) . . ?
C44 C43 C42 121.4(3) . . ?
C45 C44 C49 119.3(3) . . ?
C45 C44 C43 123.4(3) . . ?
C49 C44 C43 117.3(3) . . ?
C44 C45 C46 120.4(4) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C47 C46 C45 120.1(4) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C46 C47 C48 119.7(4) . . ?
C46 C47 H47 120.2 . . ?
C48 C47 H47 120.2 . . ?
C47 C48 C49 120.0(4) . . ?
C47 C48 H48 120.0 . . ?
C49 C48 H48 120.0 . . ?
C44 C49 C48 120.5(4) . . ?
C44 C49 H49 119.7 . . ?
C48 C49 H49 119.7 . . ?
C9 N1 C2 108.0(3) . . ?
C9 N1 C1 128.5(3) . . ?
C2 N1 C1 123.2(3) . . ?
C33 N2 C41 111.2(3) . . ?
C33 N2 C32 123.5(3) . . ?
C41 N2 C32 124.9(3) . . ?
C22 O2 C23 116.9(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
C1 N1 1.455(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.381(4) . ?
C2 C3 1.390(5) . ?
C2 C7 1.410(5) . ?
C3 C4 1.372(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.414(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.439(4) . ?
C8 C9 1.372(4) . ?
C8 C16 1.452(4) . ?
C9 N1 1.364(4) . ?
C9 C34 1.503(4) . ?
C10 C11 1.365(4) . ?
C10 C15 1.385(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(5) . ?
C12 Cl1 1.734(3) . ?
C13 C14 1.366(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.486(4) . ?
C16 C17 1.354(4) . ?
C17 C18 1.477(5) . ?
C17 C42 1.519(4) . ?
C18 O1 1.230(4) . ?
C18 C19 1.464(5) . ?
C19 C25 1.369(5) . ?
C19 C20 1.398(5) . ?
C20 C21 1.347(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(6) . ?
C21 H21 0.9300 . ?
C22 C24 1.348(6) . ?
C22 O2 1.387(5) . ?
C23 O2 1.427(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.386(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C31 1.377(5) . ?
C26 C27 1.388(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.345(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.345(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.395(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.359(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.498(5) . ?
C32 N2 1.470(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 O3 1.216(3) . ?
C33 N2 1.349(4) . ?
C33 C34 1.551(4) . ?
C34 C35 1.514(4) . ?
C34 C42 1.576(4) . ?
C35 C41 1.375(4) . ?
C35 C36 1.378(4) . ?
C36 C37 1.394(4) . ?
C36 H36 0.9300 . ?
C37 C39 1.371(5) . ?
C37 C38 1.521(5) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.394(5) . ?
C39 H39 0.9300 . ?
C40 C41 1.379(4) . ?
C40 H40 0.9300 . ?
C41 N2 1.408(4) . ?
C42 C43 1.518(5) . ?
C42 H42 0.9800 . ?
C43 O4 1.220(4) . ?
C43 C44 1.504(4) . ?
C44 C45 1.354(5) . ?
C44 C49 1.363(5) . ?
C45 C46 1.384(5) . ?
C45 H45 0.9300 . ?
C46 C47 1.357(6) . ?
C46 H46 0.9300 . ?
C47 C48 1.361(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.376(5) . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
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
N1 C2 C3 C4 -179.7(4) . . . . ?
C7 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C4 C5 C6 C7 -0.8(6) . . . . ?
N1 C2 C7 C6 178.9(3) . . . . ?
C3 C2 C7 C6 -0.1(5) . . . . ?
N1 C2 C7 C8 0.4(4) . . . . ?
C3 C2 C7 C8 -178.7(3) . . . . ?
C5 C6 C7 C2 1.0(5) . . . . ?
C5 C6 C7 C8 179.0(4) . . . . ?
C2 C7 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C9 -177.3(3) . . . . ?
C2 C7 C8 C16 -179.4(3) . . . . ?
C6 C7 C8 C16 2.4(6) . . . . ?
C7 C8 C9 N1 -1.8(3) . . . . ?
C16 C8 C9 N1 178.5(3) . . . . ?
C7 C8 C9 C34 -175.6(3) . . . . ?
C16 C8 C9 C34 4.6(4) . . . . ?
C15 C10 C11 C12 3.0(6) . . . . ?
C10 C11 C12 C13 -1.1(6) . . . . ?
C10 C11 C12 Cl1 179.8(3) . . . . ?
C11 C12 C13 C14 -1.0(6) . . . . ?
Cl1 C12 C13 C14 178.2(3) . . . . ?
C12 C13 C14 C15 1.2(6) . . . . ?
C13 C14 C15 C10 0.7(5) . . . . ?
C13 C14 C15 C16 -177.7(3) . . . . ?
C11 C10 C15 C14 -2.8(5) . . . . ?
C11 C10 C15 C16 175.5(3) . . . . ?
C9 C8 C16 C17 7.3(4) . . . . ?
C7 C8 C16 C17 -172.4(3) . . . . ?
C9 C8 C16 C15 -176.9(3) . . . . ?
C7 C8 C16 C15 3.4(5) . . . . ?
C14 C15 C16 C17 67.3(4) . . . . ?
C10 C15 C16 C17 -111.0(4) . . . . ?
C14 C15 C16 C8 -108.4(3) . . . . ?
C10 C15 C16 C8 73.3(4) . . . . ?
C8 C16 C17 C18 172.2(3) . . . . ?
C15 C16 C17 C18 -3.5(5) . . . . ?
C8 C16 C17 C42 7.8(5) . . . . ?
C15 C16 C17 C42 -167.8(3) . . . . ?
C16 C17 C18 O1 -144.4(4) . . . . ?
C42 C17 C18 O1 21.0(5) . . . . ?
C16 C17 C18 C19 36.7(6) . . . . ?
C42 C17 C18 C19 -157.9(3) . . . . ?
O1 C18 C19 C25 -136.9(4) . . . . ?
C17 C18 C19 C25 41.9(6) . . . . ?
O1 C18 C19 C20 40.0(6) . . . . ?
C17 C18 C19 C20 -141.1(4) . . . . ?
C25 C19 C20 C21 -2.4(6) . . . . ?
C18 C19 C20 C21 -179.6(4) . . . . ?
C19 C20 C21 C22 -1.4(7) . . . . ?
C20 C21 C22 C24 5.7(8) . . . . ?
C20 C21 C22 O2 -173.7(5) . . . . ?
C21 C22 C24 C25 -5.8(8) . . . . ?
O2 C22 C24 C25 173.5(5) . . . . ?
C20 C19 C25 C24 2.2(6) . . . . ?
C18 C19 C25 C24 179.2(4) . . . . ?
C22 C24 C25 C19 1.9(7) . . . . ?
C31 C26 C27 C28 -1.2(7) . . . . ?
C26 C27 C28 C29 1.4(8) . . . . ?
C27 C28 C29 C30 -0.3(8) . . . . ?
C28 C29 C30 C31 -1.0(7) . . . . ?
C29 C30 C31 C26 1.2(6) . . . . ?
C29 C30 C31 C32 -177.3(4) . . . . ?
C27 C26 C31 C30 -0.1(6) . . . . ?
C27 C26 C31 C32 178.4(4) . . . . ?
C30 C31 C32 N2 -64.7(4) . . . . ?
C26 C31 C32 N2 116.8(4) . . . . ?
N1 C9 C34 C35 32.1(4) . . . . ?
C8 C9 C34 C35 -155.1(3) . . . . ?
N1 C9 C34 C33 -85.8(3) . . . . ?
C8 C9 C34 C33 87.1(3) . . . . ?
N1 C9 C34 C42 159.5(3) . . . . ?
C8 C9 C34 C42 -27.6(4) . . . . ?
O3 C33 C34 C9 -41.4(4) . . . . ?
N2 C33 C34 C9 138.7(3) . . . . ?
O3 C33 C34 C35 -170.5(3) . . . . ?
N2 C33 C34 C35 9.6(3) . . . . ?
O3 C33 C34 C42 75.9(4) . . . . ?
N2 C33 C34 C42 -103.9(3) . . . . ?
C9 C34 C35 C41 -131.5(3) . . . . ?
C33 C34 C35 C41 -9.5(3) . . . . ?
C42 C34 C35 C41 101.0(3) . . . . ?
C9 C34 C35 C36 55.6(4) . . . . ?
C33 C34 C35 C36 177.5(3) . . . . ?
C42 C34 C35 C36 -72.0(4) . . . . ?
C41 C35 C36 C37 -2.2(5) . . . . ?
C34 C35 C36 C37 170.0(3) . . . . ?
C35 C36 C37 C39 0.9(5) . . . . ?
C35 C36 C37 C38 -175.4(3) . . . . ?
C36 C37 C39 C40 1.3(6) . . . . ?
C38 C37 C39 C40 177.6(3) . . . . ?
C37 C39 C40 C41 -2.1(5) . . . . ?
C36 C35 C41 C40 1.4(5) . . . . ?
C34 C35 C41 C40 -172.5(3) . . . . ?
C36 C35 C41 N2 -179.6(3) . . . . ?
C34 C35 C41 N2 6.5(3) . . . . ?
C39 C40 C41 C35 0.8(5) . . . . ?
C39 C40 C41 N2 -178.0(3) . . . . ?
C16 C17 C42 C43 93.6(3) . . . . ?
C18 C17 C42 C43 -72.8(4) . . . . ?
C16 C17 C42 C34 -32.3(4) . . . . ?
C18 C17 C42 C34 161.2(3) . . . . ?
C9 C34 C42 C43 -84.0(3) . . . . ?
C35 C34 C42 C43 49.9(3) . . . . ?
C33 C34 C42 C43 158.2(3) . . . . ?
C9 C34 C42 C17 39.7(4) . . . . ?
C35 C34 C42 C17 173.5(3) . . . . ?
C33 C34 C42 C17 -78.2(3) . . . . ?
C17 C42 C43 O4 -45.4(4) . . . . ?
C34 C42 C43 O4 81.6(4) . . . . ?
C17 C42 C43 C44 136.6(3) . . . . ?
C34 C42 C43 C44 -96.4(4) . . . . ?
O4 C43 C44 C45 160.5(4) . . . . ?
C42 C43 C44 C45 -21.5(5) . . . . ?
O4 C43 C44 C49 -18.3(5) . . . . ?
C42 C43 C44 C49 159.8(3) . . . . ?
C49 C44 C45 C46 -0.4(6) . . . . ?
C43 C44 C45 C46 -179.1(4) . . . . ?
C44 C45 C46 C47 -1.2(7) . . . . ?
C45 C46 C47 C48 1.8(7) . . . . ?
C46 C47 C48 C49 -1.0(7) . . . . ?
C45 C44 C49 C48 1.2(5) . . . . ?
C43 C44 C49 C48 -179.9(3) . . . . ?
C47 C48 C49 C44 -0.6(6) . . . . ?
C8 C9 N1 C2 2.0(3) . . . . ?
C34 C9 N1 C2 175.6(3) . . . . ?
C8 C9 N1 C1 -171.1(3) . . . . ?
C34 C9 N1 C1 2.4(5) . . . . ?
C3 C2 N1 C9 177.5(4) . . . . ?
C7 C2 N1 C9 -1.4(3) . . . . ?
C3 C2 N1 C1 -8.9(5) . . . . ?
C7 C2 N1 C1 172.1(3) . . . . ?
O3 C33 N2 C41 173.7(3) . . . . ?
C34 C33 N2 C41 -6.4(3) . . . . ?
O3 C33 N2 C32 0.5(5) . . . . ?
C34 C33 N2 C32 -179.6(3) . . . . ?
C35 C41 N2 C33 0.0(4) . . . . ?
C40 C41 N2 C33 179.0(3) . . . . ?
C35 C41 N2 C32 173.2(3) . . . . ?
C40 C41 N2 C32 -7.9(5) . . . . ?
C31 C32 N2 C33 98.5(4) . . . . ?
C31 C32 N2 C41 -73.8(4) . . . . ?
C24 C22 O2 C23 -10.8(10) . . . . ?
C21 C22 O2 C23 168.5(7) . . . . ?
