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#$Date: 2023-07-06 11:35:44 +0300 (Thu, 06 Jul 2023) $
#$Revision: 285036 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107439.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_8107439
loop_
_publ_author_name
'Xu, Xiaona'
'Zhu, Zhoujing'
'Liu, Bin'
_publ_section_title
;
 Crystal structure of methyl
 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]
 indole-3-carboxylate, C23H21ClN2O5
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              355
_journal_page_last               357
_journal_paper_doi               10.1515/ncrs-2022-0579
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H21 Cl N2 O5'
_chemical_formula_sum            'C23 H21 Cl N2 O5'
_chemical_formula_weight         440.87
_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
_cell_angle_alpha                90
_cell_angle_beta                 109.869(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.191(3)
_cell_length_b                   10.725(5)
_cell_length_c                   11.2390(10)
_cell_measurement_reflns_used    81
_cell_measurement_temperature    173
_cell_measurement_theta_max      18.40
_cell_measurement_theta_min      2.71
_cell_volume                     1041.9(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.00
_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  0.0869
_diffrn_reflns_av_unetI/netI     0.1059
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11717
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.927
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4215
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1383 before and 0.0813 after correction. The Ratio of minimum to maximum transmission is 0.5656. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 968 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_extinction_coef       0.020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4233
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.246
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0609
_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)+(0.0766P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1695
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2829
_reflns_number_total             4233
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0579_suppl.cif
_cod_data_source_block           m
_cod_database_code               8107439
_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   0.974
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H11-H15B
 3 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C17(H17), C19(H19), C20(H20), C21(H21), N2(H2)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
;
_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
C1 C 0.2645(7) 0.2216(6) 0.6401(5) 0.0426(15) Uani 1 1 d . . . . .
H1 H 0.285300 0.288531 0.698952 0.051 Uiso 1 1 calc R U . . .
C2 C 0.2079(8) 0.1094(7) 0.6644(6) 0.0481(16) Uani 1 1 d . . . . .
H2A H 0.190859 0.098569 0.742510 0.058 Uiso 1 1 calc R U . . .
C3 C 0.1749(7) 0.0113(6) 0.5788(6) 0.0451(16) Uani 1 1 d . . . . .
H3 H 0.134250 -0.064213 0.598746 0.054 Uiso 1 1 calc R U . . .
C4 C 0.2007(7) 0.0219(6) 0.4638(6) 0.0418(15) Uani 1 1 d . . . . .
H4 H 0.179874 -0.045717 0.405795 0.050 Uiso 1 1 calc R U . . .
C5 C 0.2579(6) 0.1349(6) 0.4367(5) 0.0332(13) Uani 1 1 d . . . . .
C6 C 0.2898(6) 0.2327(6) 0.5255(5) 0.0365(13) Uani 1 1 d . . . . .
C7 C 0.3026(6) 0.1803(5) 0.3327(5) 0.0314(12) Uani 1 1 d . . . . .
C8 C 0.3601(6) 0.2961(5) 0.3631(5) 0.0334(12) Uani 1 1 d . . . . .
C9 C 0.4143(6) 0.3833(5) 0.2825(5) 0.0321(13) Uani 1 1 d . . . . .
H9 H 0.515298 0.420521 0.335548 0.039 Uiso 1 1 calc R U . . .
C10 C 0.3042(7) 0.1203(6) 0.2131(6) 0.0394(14) Uani 1 1 d . . . . .
H10A H 0.208904 0.141412 0.142153 0.047 Uiso 1 1 calc R U . . .
H10B H 0.310720 0.028470 0.222698 0.047 Uiso 1 1 calc R U . . .
C11 C 0.4444(6) 0.1701(6) 0.1885(5) 0.0354(13) Uani 1 1 d . . . . .
H11 H 0.442813 0.136165 0.105160 0.042 Uiso 1 1 calc DR U . . .
C12 C 0.5882(7) 0.1219(6) 0.2881(6) 0.0378(14) Uani 1 1 d . . . . .
C13 C 0.8295(8) 0.1653(8) 0.4436(7) 0.068(2) Uani 1 1 d . . . . .
H13A H 0.907332 0.144583 0.405014 0.102 Uiso 1 1 calc R U . . .
H13B H 0.806145 0.091026 0.484628 0.102 Uiso 1 1 calc R U . . .
H13C H 0.869466 0.231161 0.506745 0.102 Uiso 1 1 calc R U . . .
C14 C 0.4865(6) 0.3753(6) 0.0943(5) 0.0366(14) Uani 1 1 d . . . . .
C15 C 0.5344(7) 0.3098(7) -0.0085(6) 0.0468(16) Uani 1 1 d . . . . .
H15A H 0.513610 0.364401 -0.083512 0.056 Uiso 1 1 calc R U . . .
H15B H 0.475511 0.231354 -0.035111 0.056 Uiso 1 1 calc DR U . . .
C16 C 0.2958(6) 0.4872(5) 0.2375(5) 0.0307(12) Uani 1 1 d . . . . .
C17 C 0.3374(6) 0.6075(5) 0.2745(6) 0.0376(14) Uani 1 1 d . . . . .
H17 H 0.441750 0.626089 0.323329 0.045 Uiso 1 1 calc R U . . .
C18 C 0.0764(6) 0.6755(6) 0.1725(5) 0.0358(13) Uani 1 1 d . . . . .
C19 C 0.0336(6) 0.5546(6) 0.1356(6) 0.0381(14) Uani 1 1 d . . . . .
H19 H -0.071104 0.536261 0.087695 0.046 Uiso 1 1 calc R U . . .
C20 C 0.2282(6) 0.7026(6) 0.2412(6) 0.0399(14) Uani 1 1 d . . . . .
H20 H 0.258191 0.786100 0.265793 0.048 Uiso 1 1 calc R U . . .
C21 C 0.1410(6) 0.4605(6) 0.1676(6) 0.0391(14) Uani 1 1 d . . . . .
H21 H 0.110442 0.377219 0.142435 0.047 Uiso 1 1 calc R U . . .
C22 C -0.0450(6) 0.7746(6) 0.1379(5) 0.0355(13) Uani 1 1 d . . . . .
C23 C -0.1027(8) 0.9857(7) 0.1594(7) 0.0541(18) Uani 1 1 d . . . . .
H23A H -0.163124 0.989583 0.068951 0.081 Uiso 1 1 calc R U . . .
H23B H -0.049087 1.065147 0.186573 0.081 Uiso 1 1 calc R U . . .
H23C H -0.172043 0.969644 0.207419 0.081 Uiso 1 1 calc R U . . .
Cl1 Cl 0.7351(2) 0.2778(3) 0.0582(2) 0.0841(8) Uani 1 1 d . . . . .
N1 N 0.4391(5) 0.3099(4) 0.1784(4) 0.0309(10) Uani 1 1 d . . . . .
N2 N 0.3530(5) 0.3302(5) 0.4795(4) 0.0382(12) Uani 1 1 d . . . . .
H2 H 0.383633 0.401933 0.517862 0.046 Uiso 1 1 calc R U . . .
O1 O 0.6046(6) 0.0126(5) 0.3108(5) 0.0628(14) Uani 1 1 d . . . . .
O2 O 0.6891(5) 0.2086(4) 0.3462(4) 0.0520(12) Uani 1 1 d . . . . .
O3 O 0.4932(5) 0.4890(4) 0.0975(4) 0.0493(12) Uani 1 1 d . . . . .
O4 O -0.1783(5) 0.7561(4) 0.0792(4) 0.0505(11) Uani 1 1 d . . . . .
O5 O 0.0094(5) 0.8865(4) 0.1820(4) 0.0480(12) 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'
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
C2 C1 H1 121.6 . .
C2 C1 C6 116.9(6) . .
C6 C1 H1 121.6 . .
C1 C2 H2A 118.8 . .
C1 C2 C3 122.3(6) . .
C3 C2 H2A 118.8 . .
C2 C3 H3 119.5 . .
C2 C3 C4 121.0(6) . .
C4 C3 H3 119.5 . .
C3 C4 H4 121.0 . .
C3 C4 C5 117.9(6) . .
C5 C4 H4 121.0 . .
C4 C5 C6 119.7(5) . .
C4 C5 C7 134.4(5) . .
C6 C5 C7 105.9(5) . .
C1 C6 C5 122.3(6) . .
N2 C6 C1 129.5(6) . .
N2 C6 C5 108.2(5) . .
C5 C7 C10 132.3(5) . .
C8 C7 C5 107.4(5) . .
C8 C7 C10 120.1(5) . .
C7 C8 C9 127.2(5) . .
C7 C8 N2 110.1(5) . .
N2 C8 C9 122.6(5) . .
C8 C9 H9 108.7 . .
C8 C9 C16 108.1(4) . .
C16 C9 H9 108.7 . .
N1 C9 C8 108.4(4) . .
N1 C9 H9 108.7 . .
N1 C9 C16 114.2(4) . .
C7 C10 H10A 110.4 . .
C7 C10 H10B 110.4 . .
C7 C10 C11 106.4(5) . .
H10A C10 H10B 108.6 . .
C11 C10 H10A 110.4 . .
C11 C10 H10B 110.4 . .
C10 C11 H11 107.6 . .
C12 C11 C10 109.4(5) . .
C12 C11 H11 107.6 . .
N1 C11 C10 111.1(5) . .
N1 C11 H11 107.6 . .
N1 C11 C12 113.3(5) . .
O1 C12 C11 120.6(6) . .
O1 C12 O2 124.6(6) . .
O2 C12 C11 114.8(5) . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O2 C13 H13A 109.5 . .
O2 C13 H13B 109.5 . .
O2 C13 H13C 109.5 . .
N1 C14 C15 121.8(5) . .
O3 C14 C15 117.0(5) . .
O3 C14 N1 121.3(5) . .
C14 C15 H15A 110.3 . .
C14 C15 H15B 110.3 . .
C14 C15 Cl1 107.0(4) . .
H15A C15 H15B 108.6 . .
Cl1 C15 H15A 110.3 . .
Cl1 C15 H15B 110.3 . .
C17 C16 C9 119.7(5) . .
C17 C16 C21 119.2(5) . .
C21 C16 C9 120.8(5) . .
C16 C17 H17 119.7 . .
C16 C17 C20 120.5(5) . .
C20 C17 H17 119.7 . .
C19 C18 C22 118.7(5) . .
C20 C18 C19 120.0(5) . .
C20 C18 C22 121.4(5) . .
C18 C19 H19 119.8 . .
C21 C19 C18 120.5(5) . .
C21 C19 H19 119.8 . .
C17 C20 H20 120.1 . .
C18 C20 C17 119.8(6) . .
C18 C20 H20 120.1 . .
C16 C21 H21 120.0 . .
C19 C21 C16 120.0(6) . .
C19 C21 H21 120.0 . .
O4 C22 C18 124.1(6) . .
O4 C22 O5 122.8(5) . .
O5 C22 C18 113.1(5) . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
O5 C23 H23A 109.5 . .
O5 C23 H23B 109.5 . .
O5 C23 H23C 109.5 . .
C9 N1 C11 118.5(4) . .
C14 N1 C9 116.3(5) . .
C14 N1 C11 123.8(5) . .
C6 N2 C8 108.4(5) . .
C6 N2 H2 125.8 . .
C8 N2 H2 125.8 . .
C12 O2 C13 116.2(5) . .
C22 O5 C23 116.4(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9500 .
C1 C2 1.375(10) .
C1 C6 1.390(8) .
C2 H2A 0.9500 .
C2 C3 1.388(10) .
C3 H3 0.9500 .
C3 C4 1.395(9) .
C4 H4 0.9500 .
C4 C5 1.396(9) .
C5 C6 1.408(8) .
C5 C7 1.449(8) .
C6 N2 1.379(8) .
C7 C8 1.347(8) .
C7 C10 1.495(8) .
C8 C9 1.500(8) .
C8 N2 1.382(7) .
C9 H9 1.0000 .
C9 C16 1.520(7) .
C9 N1 1.491(7) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C10 C11 1.505(8) .
C11 H11 1.0000 .
C11 C12 1.504(8) .
C11 N1 1.503(7) .
C12 O1 1.199(7) .
C12 O2 1.318(8) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C13 O2 1.455(7) .
C14 C15 1.540(9) .
C14 N1 1.362(7) .
C14 O3 1.221(8) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 Cl1 1.772(6) .
C16 C17 1.369(8) .
C16 C21 1.402(7) .
C17 H17 0.9500 .
C17 C20 1.391(8) .
C18 C19 1.377(8) .
C18 C20 1.376(8) .
C18 C22 1.494(8) .
C19 H19 0.9500 .
C19 C21 1.371(8) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 O4 1.195(6) .
C22 O5 1.329(8) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C23 O5 1.443(7) .
N2 H2 0.8800 .
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
C1 C2 C3 C4 1.1(10) . . . .
C1 C6 N2 C8 177.6(6) . . . .
C2 C1 C6 C5 0.7(8) . . . .
C2 C1 C6 N2 -176.0(5) . . . .
C2 C3 C4 C5 -1.1(9) . . . .
C3 C4 C5 C6 1.0(8) . . . .
C3 C4 C5 C7 177.9(6) . . . .
C4 C5 C6 C1 -0.8(8) . . . .
C4 C5 C6 N2 176.5(5) . . . .
C4 C5 C7 C8 -175.8(6) . . . .
C4 C5 C7 C10 -0.3(10) . . . .
C5 C6 N2 C8 0.6(6) . . . .
C5 C7 C8 C9 -176.8(5) . . . .
C5 C7 C8 N2 -1.1(6) . . . .
C5 C7 C10 C11 -143.8(6) . . . .
C6 C1 C2 C3 -0.9(9) . . . .
C6 C5 C7 C8 1.5(6) . . . .
C6 C5 C7 C10 177.0(6) . . . .
C7 C5 C6 C1 -178.5(5) . . . .
C7 C5 C6 N2 -1.2(6) . . . .
C7 C8 C9 C16 107.6(6) . . . .
C7 C8 C9 N1 -16.7(7) . . . .
C7 C8 N2 C6 0.4(6) . . . .
C7 C10 C11 C12 67.8(6) . . . .
C7 C10 C11 N1 -58.0(6) . . . .
C8 C7 C10 C11 31.2(7) . . . .
C8 C9 C16 C17 116.3(6) . . . .
C8 C9 C16 C21 -58.1(7) . . . .
C8 C9 N1 C11 -14.0(6) . . . .
C8 C9 N1 C14 179.0(4) . . . .
C9 C8 N2 C6 176.3(5) . . . .
C9 C16 C17 C20 -175.7(6) . . . .
C9 C16 C21 C19 175.3(6) . . . .
C10 C7 C8 C9 7.1(8) . . . .
C10 C7 C8 N2 -177.3(5) . . . .
C10 C11 C12 O1 51.8(8) . . . .
C10 C11 C12 O2 -127.6(6) . . . .
C10 C11 N1 C9 52.6(6) . . . .
C10 C11 N1 C14 -141.4(5) . . . .
C11 C12 O2 C13 179.8(5) . . . .
C12 C11 N1 C9 -71.0(6) . . . .
C12 C11 N1 C14 94.9(6) . . . .
C15 C14 N1 C9 172.8(5) . . . .
C15 C14 N1 C11 6.6(8) . . . .
C16 C9 N1 C11 -134.6(5) . . . .
C16 C9 N1 C14 58.4(6) . . . .
C16 C17 C20 C18 1.2(9) . . . .
C17 C16 C21 C19 0.9(9) . . . .
C18 C19 C21 C16 -0.5(9) . . . .
C18 C22 O5 C23 -176.2(5) . . . .
C19 C18 C20 C17 -0.8(9) . . . .
C19 C18 C22 O4 -0.4(9) . . . .
C19 C18 C22 O5 178.0(5) . . . .
C20 C18 C19 C21 0.5(9) . . . .
C20 C18 C22 O4 -179.6(6) . . . .
C20 C18 C22 O5 -1.2(8) . . . .
C21 C16 C17 C20 -1.3(9) . . . .
C22 C18 C19 C21 -178.7(6) . . . .
C22 C18 C20 C17 178.4(5) . . . .
N1 C9 C16 C17 -123.0(6) . . . .
N1 C9 C16 C21 62.6(7) . . . .
N1 C11 C12 O1 176.4(6) . . . .
N1 C11 C12 O2 -3.0(7) . . . .
N1 C14 C15 Cl1 -88.9(6) . . . .
N2 C8 C9 C16 -67.5(6) . . . .
N2 C8 C9 N1 168.2(5) . . . .
O1 C12 O2 C13 0.4(9) . . . .
O3 C14 C15 Cl1 90.9(6) . . . .
O3 C14 N1 C9 -6.9(7) . . . .
O3 C14 N1 C11 -173.2(5) . . . .
O4 C22 O5 C23 2.3(9) . . . .
