#------------------------------------------------------------------------------
#$Date: 2021-05-29 02:26:18 +0300 (Sat, 29 May 2021) $
#$Revision: 265601 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/29/1562966.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_1562966
loop_
_publ_author_name
'Tan, Jing'
'Wu, Bing'
'Chen, Tingting'
'Fan, Chen'
'Zhao, Jiannan'
'Xiong, Chaodong'
'Feng, Chunlan'
'Xiao, Ruoxuan'
'Ding, Chunyong'
'Tang, Wei'
'Zhang, Ao'
_publ_section_title
;
 Synthesis and Pharmacological Evaluation of Tetrahydro-γ-carboline
 Derivatives as Potent Anti-inflammatory Agents Targeting Cyclic GMP--AMP
 Synthase
;
_journal_name_full               'Journal of Medicinal Chemistry'
_journal_paper_doi               10.1021/acs.jmedchem.1c00398
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H21 Cl2 N3 O4'
_chemical_formula_sum            'C21 H21 Cl2 N3 O4'
_chemical_formula_weight         450.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.842(4)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   12.9023(17)
_cell_length_b                   12.7420(14)
_cell_length_c                   18.9596(19)
_cell_measurement_reflns_used    3359
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.139
_cell_measurement_theta_min      2.699
_cell_volume                     3026.5(6)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0975
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22726
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.944
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1131 before and 0.0614 after correction. The Ratio of minimum to maximum transmission is 0.8932. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       needle
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.008
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 1239 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     829
_refine_ls_number_reflns         9954
_refine_ls_number_restraints     834
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1713
_refine_ls_R_factor_gt           0.0998
_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)+(0.0641P)²+15.1438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2061
_refine_ls_wR_factor_ref         0.2543
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.862
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                5239
_reflns_number_total             9954
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jm1c00398_si_005.cif
_cod_data_source_block           mo_22020197_0m
_cod_database_code               1562966
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O7-H8
 2.1 with sigma of 0.02
 O12-H11
 2.1 with sigma of 0.02
 C41-C39 \\sim C40-C39 \\sim N4-C41 \\sim N4-C40
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C59) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C40) \\sim Ueq, Uanis(C39) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(N4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C40) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C54) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C56) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H39A(0.5) H39B(0.5) H39C(0.5) H39D(0.5) C40(0.5) H40A(0.5)
 H40B(0.5) C41(0.5) H41A(0.5) H41B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C54(H54A,H54B), C17(H17A,H17B), C56(H56A,H56B), C19(H19A,H19B), C58(H58A,
 H58B), C21(H21A,H21B), C39(H39A,H39B), C39(H39C,H39D), C43(H43A,H43B),
 C38(H38A,H38B), C55(H55A,H55B), C18(H18A,H18B), C40(H40A,H40B), C41(H41A,H41B)
6.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), N9(H9), N1(H1), N7(H7), C63(H63), N5(H5), C16(H16), C37(H37),
 C15(H15), C01I(H01I), C36(H36), C4(H4), C3(H3A), C24(H24), C50(H50), C25(H25),
 C45(H45)
6.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C), C51(H51A,H51B,H51C), C27(H27A,H27B,H27C),
 C22(H22A,H22B,H22C), C44(H44A,H44B,H44C)
6.d Idealised tetrahedral OH refined as rotating group:
 O8(H8), O11(H11), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
Cl6 Cl 0.5451(3) 0.4593(3) 0.9227(2) 0.0457(10) Uani 1 1 d . U . . .
Cl4 Cl 0.2035(3) 0.4468(4) 1.2471(2) 0.0604(14) Uani 1 1 d . U . . .
Cl5 Cl 0.4292(3) 0.6787(4) 0.92558(19) 0.0514(12) Uani 1 1 d . U . . .
Cl1 Cl -0.2463(4) 0.6501(5) 1.5864(2) 0.082(2) Uani 1 1 d . U . . .
Cl2 Cl -0.1160(3) 0.4438(4) 1.5764(3) 0.0791(19) Uani 1 1 d . U . . .
Cl3 Cl 0.0806(4) 0.6614(5) 1.2563(2) 0.0716(18) Uani 1 1 d . U . . .
O12 O 0.5973(8) 0.8906(8) 0.5421(5) 0.048(3) Uani 1 1 d D U . . .
O10 O 0.2399(8) 0.6304(9) 0.4876(5) 0.045(3) Uani 1 1 d . U . . .
O3 O -0.4400(7) 0.6409(8) 1.1509(5) 0.037(2) Uani 1 1 d . U . . .
O4 O -0.5332(7) 0.8346(7) 1.3906(5) 0.037(2) Uani 1 1 d . U . . .
O5 O -0.1928(8) 0.8340(7) 1.0608(5) 0.038(2) Uani 1 1 d . U . . .
O6 O -0.0966(8) 0.6407(8) 0.8224(5) 0.038(2) Uani 1 1 d . U . . .
O1 O -0.0592(8) 0.9100(8) 1.2191(6) 0.048(3) Uani 1 1 d . U . . .
N3 N -0.2859(8) 0.7319(8) 1.2629(5) 0.022(2) Uani 1 1 d . U . . .
H3 H -0.257660 0.718887 1.225871 0.027 Uiso 1 1 calc R . . . .
O9 O 0.1503(8) 0.8292(8) 0.7261(6) 0.041(3) Uani 1 1 d . U . . .
N6 N 0.0566(8) 0.7357(8) 0.9327(5) 0.025(2) Uani 1 1 d . U . . .
H6 H 0.085143 0.724018 0.895638 0.030 Uiso 1 1 calc R . . . .
N9 N 0.3959(9) 0.7301(8) 0.5964(6) 0.029(2) Uani 1 1 d . U . . .
H9 H 0.424472 0.719786 0.559180 0.035 Uiso 1 1 calc R . . . .
O8 O 0.1969(9) 1.0589(7) 0.8052(5) 0.044(3) Uani 1 1 d . U . . .
H8 H 0.227773 1.003664 0.797334 0.066 Uiso 1 1 calc DGR . . . .
O11 O 0.5139(9) 1.0526(8) 0.4696(5) 0.045(3) Uani 1 1 d . U . . .
H11 H 0.562373 1.011609 0.464220 0.068 Uiso 1 1 calc DGR . . . .
O7 O 0.2777(9) 0.9023(9) 0.8864(7) 0.068(4) Uani 1 1 d D U . . .
N1 N -0.2868(10) 0.7784(10) 1.4447(6) 0.043(3) Uani 1 1 d . U . . .
H1 H -0.305692 0.809144 1.481260 0.052 Uiso 1 1 calc R . . . .
O2 O -0.1419(9) 1.0627(8) 1.1347(6) 0.049(3) Uani 1 1 d . U . . .
H2 H -0.107163 1.008832 1.129350 0.073 Uiso 1 1 calc GR . . . .
N7 N 0.3989(9) 0.7972(8) 0.7787(6) 0.031(3) Uani 1 1 d . U . . .
H7 H 0.386505 0.837179 0.813599 0.038 Uiso 1 1 calc R . . . .
N8 N 0.5345(10) 0.9191(8) 0.6402(6) 0.038(3) Uani 1 1 d . U . . .
C63 C 0.5323(9) 0.5760(10) 0.7244(7) 0.024(3) Uani 1 1 d . U . . .
H63 H 0.555253 0.556406 0.682227 0.029 Uiso 1 1 calc R . . . .
N5 N 0.0523(10) 0.7905(9) 1.1147(6) 0.049(4) Uani 1 1 d . U . . .
H5 H 0.036004 0.825918 1.150418 0.059 Uiso 1 1 calc R . . . .
C57 C 0.5525(11) 0.9468(10) 0.5756(6) 0.029(3) Uani 1 1 d . U . . .
C16 C -0.1356(10) 0.5783(10) 1.3827(8) 0.028(3) Uani 1 1 d . U . . .
H16 H -0.110685 0.565776 1.340182 0.033 Uiso 1 1 calc R . . . .
N2 N -0.1648(10) 0.9265(9) 1.2975(6) 0.043(3) Uani 1 1 d . U . . .
C37 C 0.1945(9) 0.5788(10) 1.0560(7) 0.023(3) Uani 1 1 d . U . . .
H37 H 0.220784 0.563123 1.014519 0.027 Uiso 1 1 calc R . . . .
C6 C -0.4154(10) 0.7794(9) 1.3210(7) 0.021(2) Uani 1 1 d . U . . .
C48 C 0.2886(11) 0.7243(10) 0.5954(7) 0.026(3) Uani 1 1 d . U . . .
C47 C 0.2685(11) 0.7751(10) 0.6560(7) 0.029(3) Uani 1 1 d . U . . .
C9 C -0.3113(10) 0.8174(10) 1.3699(6) 0.024(2) Uani 1 1 d . U . . .
C7 C -0.3945(10) 0.7301(10) 1.2608(6) 0.023(3) Uani 1 1 d . U . . .
C42 C 0.2147(10) 0.9532(10) 0.9107(6) 0.026(3) Uani 1 1 d . U . . .
C33 C 0.1016(9) 0.6972(10) 1.1209(6) 0.022(3) Uani 1 1 d . U . . .
C60 C 0.4482(10) 0.6990(10) 0.7884(7) 0.023(3) Uani 1 1 d . U . . .
N4 N 0.1798(10) 0.9265(9) 0.9693(6) 0.039(3) Uani 1 1 d D U . . .
C59 C 0.4796(9) 0.6691(9) 0.7267(6) 0.019(2) Uani 1 1 d . U . . .
C28 C -0.0500(10) 0.7332(9) 0.9321(7) 0.024(3) Uani 1 1 d . U . . .
C29 C -0.0724(10) 0.7807(9) 0.9913(7) 0.023(2) Uani 1 1 d . U . . .
C20 C -0.1288(10) 0.9577(11) 1.2403(7) 0.031(3) Uani 1 1 d . U . . .
C11 C -0.1935(9) 0.6669(10) 1.3875(7) 0.021(3) Uani 1 1 d . U . . .
C30 C 0.0303(10) 0.8238(10) 1.0390(7) 0.026(3) Uani 1 1 d . U . . .
C61 C 0.4683(10) 0.6360(10) 0.8496(7) 0.025(3) Uani 1 1 d . U . . .
C32 C 0.1409(9) 0.6711(9) 1.0593(6) 0.019(2) Uani 1 1 d . U . . .
C34 C 0.1241(10) 0.6266(12) 1.1805(7) 0.035(3) Uani 1 1 d . U . . .
C13 C -0.2039(11) 0.6181(13) 1.5075(7) 0.039(4) Uani 1 1 d . U . . .
C5 C -0.5210(11) 0.7870(9) 1.3281(7) 0.026(3) Uani 1 1 d . U . . .
C12 C -0.2300(11) 0.6864(11) 1.4492(7) 0.032(3) Uani 1 1 d . U . . .
C10 C -0.2266(10) 0.7587(9) 1.3361(6) 0.021(2) Uani 1 1 d . U . . .
C15 C -0.1130(10) 0.5070(10) 1.4391(8) 0.033(3) Uani 1 1 d . U . . .
H15 H -0.073836 0.444979 1.435305 0.040 Uiso 1 1 calc R . . . .
C01I C 0.5518(10) 0.5104(9) 0.7857(7) 0.026(3) Uani 1 1 d . U . . .
H01I H 0.586937 0.444957 0.785242 0.031 Uiso 1 1 calc R . . . .
C52 C 0.3709(11) 0.8233(10) 0.7002(7) 0.028(3) Uani 1 1 d . U . . .
C31 C 0.1133(10) 0.7616(9) 1.0068(6) 0.023(2) Uani 1 1 d . U . . .
C23 C -0.1782(11) 0.7872(10) 0.9994(7) 0.028(3) Uani 1 1 d . U . . .
C46 C 0.1664(12) 0.7782(12) 0.6645(8) 0.039(3) Uani 1 1 d . U . . .
C36 C 0.2101(10) 0.5086(10) 1.1134(7) 0.025(3) Uani 1 1 d . U . . .
H36 H 0.242986 0.442617 1.110248 0.030 Uiso 1 1 calc R . . . .
C4 C -0.6015(11) 0.7460(10) 1.2728(7) 0.030(3) Uani 1 1 d . U . . .
H4 H -0.673762 0.752350 1.275600 0.036 Uiso 1 1 calc R . . . .
C54 C 0.3751(10) 0.9403(10) 0.6843(7) 0.031(3) Uani 1 1 d . U . . .
H54A H 0.349109 0.979569 0.721667 0.037 Uiso 1 1 calc R . . . .
H54B H 0.325461 0.954817 0.636737 0.037 Uiso 1 1 calc R . . . .
C2 C -0.4745(11) 0.6901(11) 1.2063(7) 0.030(3) Uani 1 1 d . U . . .
C53 C 0.4541(10) 0.7570(9) 0.6714(7) 0.024(2) Uani 1 1 d . U . . .
C26 C -0.1310(11) 0.6881(11) 0.8772(7) 0.031(3) Uani 1 1 d . U . . .
C17 C -0.1314(11) 0.8275(10) 1.3348(7) 0.029(3) Uani 1 1 d . U . . .
H17A H -0.091195 0.842032 1.385196 0.034 Uiso 1 1 calc R . . . .
H17B H -0.083303 0.789962 1.309754 0.034 Uiso 1 1 calc R . . . .
C56 C 0.5588(11) 0.8157(10) 0.6699(7) 0.031(3) Uani 1 1 d . U . . .
H56A H 0.604484 0.820921 0.719832 0.037 Uiso 1 1 calc R . . . .
H56B H 0.598500 0.776000 0.639943 0.037 Uiso 1 1 calc R . . . .
C19 C -0.2983(10) 0.9350(10) 1.3693(7) 0.029(3) Uani 1 1 d . U . . .
H19A H -0.366086 0.967842 1.373457 0.035 Uiso 1 1 calc R . . . .
H19B H -0.242613 0.955582 1.412721 0.035 Uiso 1 1 calc R . . . .
C3 C -0.5776(11) 0.6951(11) 1.2128(7) 0.032(3) Uani 1 1 d . U . . .
H3A H -0.633250 0.664267 1.176679 0.039 Uiso 1 1 calc R . . . .
C49 C 0.2069(12) 0.6783(13) 0.5435(8) 0.040(3) Uani 1 1 d . U . . .
C58 C 0.5052(12) 1.0488(11) 0.5415(7) 0.036(3) Uani 1 1 d . U . . .
H58A H 0.429160 1.053352 0.543137 0.043 Uiso 1 1 calc R . . . .
H58B H 0.543604 1.108886 0.568998 0.043 Uiso 1 1 calc R . . . .
C62 C 0.5187(11) 0.5423(10) 0.8475(8) 0.031(3) Uani 1 1 d . U . . .
C8 C -0.6389(12) 0.8390(13) 1.4023(9) 0.047(4) Uani 1 1 d . U . . .
H8A H -0.636865 0.874586 1.448433 0.070 Uiso 1 1 calc GR . . . .
H8B H -0.666401 0.767591 1.403961 0.070 Uiso 1 1 calc GR . . . .
H8C H -0.685633 0.877888 1.362510 0.070 Uiso 1 1 calc GR . . . .
C35 C 0.1785(10) 0.5347(11) 1.1735(7) 0.029(3) Uani 1 1 d . U . . .
C1 C -0.5106(13) 0.5746(13) 1.1047(8) 0.049(4) Uani 1 1 d . U . . .
H1A H -0.530739 0.516778 1.132764 0.074 Uiso 1 1 calc GR . . . .
H1B H -0.476300 0.546256 1.067883 0.074 Uiso 1 1 calc GR . . . .
H1C H -0.574614 0.613993 1.080726 0.074 Uiso 1 1 calc GR . . . .
C24 C -0.2572(12) 0.7412(12) 0.9456(8) 0.044(4) Uani 1 1 d . U . . .
H24 H -0.328976 0.742659 0.950099 0.052 Uiso 1 1 calc R . . . .
C51 C 0.1623(13) 0.5722(14) 0.4387(8) 0.057(5) Uani 1 1 d . U . . .
H51A H 0.142948 0.510269 0.463450 0.086 Uiso 1 1 calc GR . . . .
H51B H 0.190854 0.549866 0.397666 0.086 Uiso 1 1 calc GR . . . .
H51C H 0.098831 0.615781 0.420960 0.086 Uiso 1 1 calc GR . . . .
C27 C -0.1725(12) 0.5794(13) 0.7716(8) 0.047(4) Uani 1 1 d . U . . .
H27A H -0.136393 0.543421 0.738534 0.070 Uiso 1 1 calc GR . . . .
H27B H -0.228215 0.625470 0.743657 0.070 Uiso 1 1 calc GR . . . .
H27C H -0.204786 0.527391 0.797871 0.070 Uiso 1 1 calc GR . . . .
C14 C -0.1483(10) 0.5270(11) 1.5015(9) 0.037(3) Uani 1 1 d . U . . .
C50 C 0.1052(13) 0.6836(15) 0.5527(9) 0.055(5) Uani 1 1 d . U . . .
H50 H 0.048904 0.653271 0.516886 0.066 Uiso 1 1 calc R . . . .
C22 C -0.2987(13) 0.8372(13) 1.0710(10) 0.057(5) Uani 1 1 d . U . . .
H22A H -0.343940 0.879208 1.032303 0.085 Uiso 1 1 calc GR . . . .
H22B H -0.297804 0.868907 1.118220 0.085 Uiso 1 1 calc GR . . . .
H22C H -0.327100 0.765699 1.069417 0.085 Uiso 1 1 calc GR . . . .
C21 C -0.1785(13) 1.0531(11) 1.1974(8) 0.046(4) Uani 1 1 d . U . . .
H21A H -0.257215 1.045993 1.184475 0.055 Uiso 1 1 calc R . . . .
H21B H -0.159857 1.116986 1.227484 0.055 Uiso 1 1 calc R . . . .
C39 C 0.0399(11) 0.9416(10) 1.0323(8) 0.037(3) Uani 1 1 d D U . . .
H39A H -0.030442 0.973089 1.031740 0.045 Uiso 0.5 1 calc R . P A 1
H39B H 0.091001 0.967438 1.076403 0.045 Uiso 0.5 1 calc R . P A 1
H39C H 0.023336 0.973492 1.075906 0.045 Uiso 0.5 1 calc R . P B 2
H39D H -0.016807 0.964268 0.990003 0.045 Uiso 0.5 1 calc R . P B 2
C43 C 0.1672(14) 1.0499(11) 0.8706(8) 0.045(4) Uani 1 1 d . U . . .
H43A H 0.088399 1.046484 0.861129 0.054 Uiso 1 1 calc R . . . .
H43B H 0.191573 1.112540 0.900841 0.054 Uiso 1 1 calc R . . . .
C25 C -0.2344(12) 0.6937(14) 0.8860(8) 0.050(4) Uani 1 1 d . U . . .
H25 H -0.290889 0.663930 0.850050 0.060 Uiso 1 1 calc R . . . .
C44 C 0.0472(12) 0.8330(14) 0.7387(9) 0.057(5) Uani 1 1 d . U . . .
H44A H 0.049879 0.869365 0.784671 0.085 Uiso 1 1 calc GR . . . .
H44B H 0.020556 0.761463 0.741289 0.085 Uiso 1 1 calc GR . . . .
H44C H -0.000660 0.870952 0.698929 0.085 Uiso 1 1 calc GR . . . .
C45 C 0.0811(13) 0.7317(13) 0.6127(9) 0.052(4) Uani 1 1 d . U . . .
H45 H 0.010039 0.733415 0.618638 0.062 Uiso 1 1 calc R . . . .
C38 C 0.2123(11) 0.8278(10) 1.0060(7) 0.031(3) Uani 1 1 d . U . . .
H38A H 0.253083 0.841399 1.056373 0.037 Uiso 1 1 calc R . . . .
H38B H 0.259025 0.789159 0.980468 0.037 Uiso 1 1 calc R . . . .
C55 C 0.4854(13) 0.9820(13) 0.6824(9) 0.048(4) Uani 1 1 d . U . . .
H55A H 0.478350 1.054194 0.662541 0.058 Uiso 1 1 calc R . . . .
H55B H 0.530672 0.985058 0.732542 0.058 Uiso 1 1 calc R . . . .
C18 C -0.2708(13) 0.9756(13) 1.3083(9) 0.049(4) Uani 1 1 d . U . . .
H18A H -0.262450 1.052607 1.313371 0.059 Uiso 1 1 calc R . . . .
H18B H -0.329016 0.961164 1.264793 0.059 Uiso 1 1 calc R . . . .
C40 C 0.0729(16) 0.979(2) 0.9712(12) 0.029(5) Uani 0.5 1 d D U P C 1
H40A H 0.081785 1.056265 0.974318 0.035 Uiso 0.5 1 calc R . P C 1
H40B H 0.018333 0.962305 0.926249 0.035 Uiso 0.5 1 calc R . P C 1
C41 C 0.1451(17) 0.9895(19) 1.0236(12) 0.033(5) Uani 0.5 1 d D U P C 2
H41A H 0.134201 1.063408 1.007428 0.040 Uiso 0.5 1 calc R . P C 2
H41B H 0.199327 0.987578 1.070428 0.040 Uiso 0.5 1 calc R . P C 2
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'
Cl Cl 0.1484 0.1585 '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
C49 O10 C51 116.1(12) . . ?
C2 O3 C1 118.2(11) . . ?
C5 O4 C8 117.5(11) . . ?
C23 O5 C22 117.5(11) . . ?
C26 O6 C27 117.3(11) . . ?
C7 N3 C10 109.1(10) . . ?
C46 O9 C44 119.6(12) . . ?
C28 N6 C31 106.4(10) . . ?
C48 N9 C53 107.5(10) . . ?
C12 N1 C9 109.8(11) . . ?
C60 N7 C52 109.2(10) . . ?
C57 N8 C56 121.9(11) . . ?
C57 N8 C55 125.1(13) . . ?
C55 N8 C56 113.0(11) . . ?
C59 C63 C01I 118.7(12) . . ?
C33 N5 C30 108.7(11) . . ?
O12 C57 N8 122.4(13) . . ?
O12 C57 C58 119.1(11) . . ?
N8 C57 C58 118.2(12) . . ?
C11 C16 C15 120.6(14) . . ?
C20 N2 C17 122.0(11) . . ?
C20 N2 C18 118.2(12) . . ?
C17 N2 C18 116.7(11) . . ?
C32 C37 C36 119.8(12) . . ?
C7 C6 C9 109.3(11) . . ?
C7 C6 C5 119.6(12) . . ?
C5 C6 C9 131.1(11) . . ?
N9 C48 C47 110.3(11) . . ?
N9 C48 C49 128.4(12) . . ?
C49 C48 C47 121.3(13) . . ?
C48 C47 C52 109.5(12) . . ?
C46 C47 C48 119.1(13) . . ?
C46 C47 C52 131.4(13) . . ?
N1 C9 C6 116.0(11) . . ?
N1 C9 C10 102.8(9) . . ?
N1 C9 C19 110.3(11) . . ?
C6 C9 C10 101.4(10) . . ?
C19 C9 C6 113.3(10) . . ?
C19 C9 C10 112.2(11) . . ?
C6 C7 N3 111.2(11) . . ?
C2 C7 N3 126.7(12) . . ?
C2 C7 C6 122.0(12) . . ?
O7 C42 N4 124.6(13) . . ?
O7 C42 C43 118.4(12) . . ?
N4 C42 C43 116.9(12) . . ?
N5 C33 C32 113.0(12) . . ?
N5 C33 C34 129.5(12) . . ?
C32 C33 C34 117.5(11) . . ?
C59 C60 N7 110.6(11) . . ?
C59 C60 C61 121.1(11) . . ?
C61 C60 N7 128.2(12) . . ?
C42 N4 C38 120.2(12) . . ?
C42 N4 C40 112.9(13) . . ?
C42 N4 C41 131.9(14) . . ?
C38 N4 C40 121.6(12) . . ?
C38 N4 C41 103.9(14) . . ?
C63 C59 C60 120.8(12) . . ?
C63 C59 C53 130.1(12) . . ?
C60 C59 C53 108.9(10) . . ?
N6 C28 C26 125.3(12) . . ?
C29 C28 N6 113.1(11) . . ?
C29 C28 C26 121.6(13) . . ?
C28 C29 C30 108.9(12) . . ?
C28 C29 C23 121.0(12) . . ?
C23 C29 C30 130.1(12) . . ?
O1 C20 N2 122.7(13) . . ?
O1 C20 C21 118.0(12) . . ?
N2 C20 C21 119.2(12) . . ?
C16 C11 C12 120.4(12) . . ?
C16 C11 C10 131.9(12) . . ?
C12 C11 C10 107.7(10) . . ?
N5 C30 C29 114.7(12) . . ?
N5 C30 C31 104.2(10) . . ?
N5 C30 C39 111.7(11) . . ?
C29 C30 C31 99.5(10) . . ?
C39 C30 C29 112.7(10) . . ?
C39 C30 C31 113.0(12) . . ?
C60 C61 Cl5 119.0(10) . . ?
C62 C61 Cl5 122.5(10) . . ?
C62 C61 C60 118.6(13) . . ?
C37 C32 C33 121.4(12) . . ?
C37 C32 C31 131.8(12) . . ?
C33 C32 C31 106.8(10) . . ?
C33 C34 Cl3 117.1(11) . . ?
C35 C34 Cl3 124.8(11) . . ?
C35 C34 C33 118.1(13) . . ?
C12 C13 Cl1 117.8(12) . . ?
C14 C13 Cl1 122.5(11) . . ?
C14 C13 C12 119.7(14) . . ?
O4 C5 C6 115.3(12) . . ?
O4 C5 C4 126.6(12) . . ?
C4 C5 C6 118.0(12) . . ?
N1 C12 C11 112.7(11) . . ?
N1 C12 C13 127.6(13) . . ?
C11 C12 C13 119.7(12) . . ?
N3 C10 C9 103.9(10) . . ?
N3 C10 C11 115.7(10) . . ?
N3 C10 C17 111.3(10) . . ?
C11 C10 C9 102.7(9) . . ?
C17 C10 C9 112.0(10) . . ?
C17 C10 C11 110.6(10) . . ?
C16 C15 C14 119.2(13) . . ?
C62 C01I C63 119.3(11) . . ?
N7 C52 C47 115.8(11) . . ?
N7 C52 C54 114.0(11) . . ?
N7 C52 C53 101.9(10) . . ?
C47 C52 C54 110.8(10) . . ?
C47 C52 C53 99.7(10) . . ?
C54 C52 C53 113.5(11) . . ?
N6 C31 C30 105.0(10) . . ?
N6 C31 C32 116.6(10) . . ?
N6 C31 C38 109.9(10) . . ?
C32 C31 C30 101.8(10) . . ?
C32 C31 C38 111.2(10) . . ?
C38 C31 C30 112.0(10) . . ?
O5 C23 C29 116.9(12) . . ?
O5 C23 C24 125.9(13) . . ?
C24 C23 C29 117.1(13) . . ?
O9 C46 C45 121.9(14) . . ?
C47 C46 O9 117.0(13) . . ?
C47 C46 C45 121.1(15) . . ?
C35 C36 C37 119.4(12) . . ?
C5 C4 C3 121.0(12) . . ?
C52 C54 C55 115.0(11) . . ?
C7 C2 O3 114.8(12) . . ?
C3 C2 O3 125.9(12) . . ?
C3 C2 C7 119.2(13) . . ?
N9 C53 C59 118.0(10) . . ?
N9 C53 C52 103.1(10) . . ?
N9 C53 C56 109.7(10) . . ?
C59 C53 C52 102.2(10) . . ?
C59 C53 C56 108.9(10) . . ?
C56 C53 C52 114.8(10) . . ?
O6 C26 C28 115.2(12) . . ?
O6 C26 C25 127.8(12) . . ?
C25 C26 C28 117.0(13) . . ?
N2 C17 C10 111.2(11) . . ?
N8 C56 C53 109.9(11) . . ?
C18 C19 C9 115.3(12) . . ?
C2 C3 C4 120.1(12) . . ?
O10 C49 C48 114.2(12) . . ?
C50 C49 O10 127.2(13) . . ?
C50 C49 C48 118.6(14) . . ?
O11 C58 C57 109.1(11) . . ?
C61 C62 Cl6 120.6(11) . . ?
C61 C62 C01I 121.4(12) . . ?
C01I C62 Cl6 118.0(10) . . ?
C34 C35 Cl4 117.6(11) . . ?
C36 C35 Cl4 118.7(10) . . ?
C36 C35 C34 123.7(12) . . ?
C25 C24 C23 121.7(14) . . ?
C13 C14 Cl2 118.2(12) . . ?
C13 C14 C15 120.4(13) . . ?
C15 C14 Cl2 121.3(11) . . ?
C49 C50 C45 122.4(15) . . ?
O2 C21 C20 110.1(11) . . ?
C30 C39 C41 119.8(14) . . ?
C40 C39 C30 116.9(15) . . ?
O8 C43 C42 110.8(12) . . ?
C24 C25 C26 121.6(14) . . ?
C50 C45 C46 117.5(15) . . ?
N4 C38 C31 109.7(11) . . ?
N8 C55 C54 111.6(13) . . ?
C19 C18 N2 111.5(13) . . ?
C39 C40 N4 108.6(15) . . ?
N4 C41 C39 106.6(14) . . ?
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
Cl6 C62 1.742(13) . ?
Cl4 C35 1.758(13) . ?
Cl5 C61 1.724(13) . ?
Cl1 C13 1.760(15) . ?
Cl2 C14 1.741(14) . ?
Cl3 C34 1.721(15) . ?
O12 C57 1.193(15) . ?
O10 C49 1.376(17) . ?
O10 C51 1.403(16) . ?
O3 C2 1.384(16) . ?
O3 C1 1.390(15) . ?
O4 C5 1.374(15) . ?
O4 C8 1.434(16) . ?
O5 C23 1.361(16) . ?
O5 C22 1.425(18) . ?
O6 C26 1.363(16) . ?
O6 C27 1.430(15) . ?
O1 C20 1.228(15) . ?
N3 C7 1.392(16) . ?
N3 C10 1.457(15) . ?
O9 C46 1.395(17) . ?
O9 C44 1.408(17) . ?
N6 C28 1.374(16) . ?
N6 C31 1.458(15) . ?
N9 C48 1.382(16) . ?
N9 C53 1.482(15) . ?
O8 C43 1.387(16) . ?
O11 C58 1.396(15) . ?
O7 C42 1.214(16) . ?
N1 C9 1.464(15) . ?
N1 C12 1.374(17) . ?
O2 C21 1.385(15) . ?
N7 C60 1.395(16) . ?
N7 C52 1.482(16) . ?
N8 C57 1.348(15) . ?
N8 C56 1.438(17) . ?
N8 C55 1.389(17) . ?
C63 C59 1.374(16) . ?
C63 C01I 1.405(18) . ?
N5 C33 1.340(16) . ?
N5 C30 1.458(16) . ?
C57 C58 1.513(19) . ?
C16 C11 1.369(17) . ?
C16 C15 1.380(18) . ?
N2 C20 1.339(16) . ?
N2 C17 1.459(16) . ?
N2 C18 1.562(18) . ?
C37 C32 1.374(16) . ?
C37 C36 1.386(17) . ?
C6 C9 1.516(18) . ?
C6 C7 1.386(17) . ?
C6 C5 1.404(18) . ?
C48 C47 1.397(18) . ?
C48 C49 1.388(18) . ?
C47 C52 1.515(18) . ?
C47 C46 1.36(2) . ?
C9 C10 1.581(17) . ?
C9 C19 1.509(18) . ?
C7 C2 1.372(17) . ?
C42 N4 1.338(16) . ?
C42 C43 1.500(19) . ?
C33 C32 1.419(17) . ?
C33 C34 1.419(18) . ?
C60 C59 1.381(17) . ?
C60 C61 1.383(17) . ?
N4 C38 1.449(16) . ?
N4 C40 1.542(19) . ?
N4 C41 1.459(18) . ?
C59 C53 1.514(16) . ?
C28 C29 1.365(17) . ?
C28 C26 1.410(17) . ?
C29 C30 1.517(17) . ?
C29 C23 1.413(18) . ?
C20 C21 1.518(18) . ?
C11 C12 1.384(17) . ?
C11 C10 1.518(16) . ?
C30 C31 1.568(18) . ?
C30 C39 1.514(18) . ?
C61 C62 1.364(18) . ?
C32 C31 1.509(16) . ?
C34 C35 1.388(19) . ?
C13 C12 1.383(18) . ?
C13 C14 1.38(2) . ?
C5 C4 1.389(18) . ?
C10 C17 1.514(17) . ?
C15 C14 1.39(2) . ?
C01I C62 1.400(18) . ?
C52 C54 1.524(17) . ?
C52 C53 1.564(18) . ?
C31 C38 1.534(18) . ?
C23 C24 1.387(18) . ?
C46 C45 1.42(2) . ?
C36 C35 1.340(18) . ?
C4 C3 1.406(18) . ?
C54 C55 1.528(19) . ?
C2 C3 1.367(19) . ?
C53 C56 1.550(17) . ?
C26 C25 1.39(2) . ?
C19 C18 1.388(18) . ?
C49 C50 1.37(2) . ?
C24 C25 1.37(2) . ?
C50 C45 1.39(2) . ?
C39 C40 1.410(19) . ?
C39 C41 1.533(19) . ?
