#------------------------------------------------------------------------------
#$Date: 2024-07-05 04:37:37 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292750 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160027.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_7160027
loop_
_publ_author_name
'Mandal, Arnab'
'Singh, Satyajit'
'Arora, Arisha'
'Nambiar, Sujisha S.'
'Ghosh, Siddhartha S.'
'Khan, Abu Taleb'
_publ_section_title
;
 L-Proline-catalysed synthesis of chromeno[2,3-b]chromene from
 4-hydroxy-2H-chromene-2-thione and an anti-proliferative study.
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5333
_journal_page_last               5345
_journal_paper_doi               10.1039/d4ob00509k
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C24 H19 Cl O4'
_chemical_formula_sum            'C24 H19 Cl O4'
_chemical_formula_weight         406.868
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-24 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.051(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1059(15)
_cell_length_b                   21.916(4)
_cell_length_c                   10.1282(17)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.57
_cell_measurement_theta_min      2.28
_cell_volume                     1951.9(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.00
_diffrn_measured_fraction_theta_full 0.9940
_diffrn_measured_fraction_theta_max 0.9774
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.9940
_diffrn_reflns_Laue_measured_fraction_max 0.9774
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            41936
_diffrn_reflns_point_group_measured_fraction_full 0.9940
_diffrn_reflns_point_group_measured_fraction_max 0.9774
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.23
_diffrn_reflns_theta_min         1.86
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5983
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1304 before and 0.0946 after correction.
The Ratio of minimum to maximum transmission is 0.8028.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             849.114
_refine_diff_density_max         0.7927
_refine_diff_density_min         -0.5884
_refine_diff_density_rms         0.1348
_refine_ls_d_res_high            0.8039
_refine_ls_d_res_low             10.9579
_refine_ls_goodness_of_fit_ref   1.0494
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0494
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0896
_refine_ls_shift/su_max          -0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1428P)²+6.0540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2752
_refine_ls_wR_factor_ref         0.2848
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                3059
_reflns_number_total             3852
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob00509k2.cif
_cod_data_source_block           AM_02_0m_a
_cod_database_code               7160027
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C14(H14), C15(H15), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
Cl1 Cl 0.52986(16) 0.48395(6) 0.81878(12) 0.0510(4) Uani 1.000000 .
O1 O 0.5121(4) 0.35747(15) 0.2832(3) 0.0401(8) Uani 1.000000 .
O2 O 0.2827(4) 0.38563(15) 0.1874(3) 0.0395(8) Uani 1.000000 .
O3 O 0.8078(4) 0.3939(2) 0.7337(4) 0.0674(13) Uani 1.000000 .
O4 O 0.2351(4) 0.47546(19) 0.5267(3) 0.0549(10) Uani 1.000000 .
C1 C 1.0276(6) 0.2792(3) 0.4229(6) 0.0625(17) Uani 1.000000 .
H1a H 1.0019(15) 0.2459(14) 0.360(4) 0.094(2) Uiso 1.000000 GR
H1b H 1.062(3) 0.3132(7) 0.379(4) 0.094(2) Uiso 1.000000 GR
H1c H 1.1068(19) 0.267(2) 0.5007(8) 0.094(2) Uiso 1.000000 GR
C2 C 0.8877(5) 0.2979(3) 0.4693(4) 0.0436(11) Uani 1.000000 .
C3 C 0.7671(5) 0.3233(2) 0.3471(4) 0.0404(11) Uani 1.000000 .
H3a H 0.8146(5) 0.3517(2) 0.2975(4) 0.0485(13) Uiso 1.000000 R
H3b H 0.7245(5) 0.2901(2) 0.2858(4) 0.0485(13) Uiso 1.000000 R
C4 C 0.6425(5) 0.3550(2) 0.3905(4) 0.0329(9) Uani 1.000000 .
C5 C 0.3910(5) 0.3870(2) 0.3058(4) 0.0334(9) Uani 1.000000 .
C6 C 0.1451(5) 0.4142(2) 0.1848(4) 0.0356(10) Uani 1.000000 .
C7 C 0.1233(5) 0.4448(2) 0.2970(4) 0.0352(10) Uani 1.000000 .
C8 C -0.0179(6) 0.4723(2) 0.2853(5) 0.0464(12) Uani 1.000000 .
H8 H -0.0363(6) 0.4930(2) 0.3595(5) 0.0557(14) Uiso 1.000000 R
C9 C -0.1297(6) 0.4689(3) 0.1645(6) 0.0548(14) Uani 1.000000 .
H9 H -0.2235(6) 0.4873(3) 0.1575(6) 0.0658(16) Uiso 1.000000 R
C10 C 0.8268(7) 0.2422(3) 0.5268(6) 0.0625(16) Uani 1.000000 .
H10a H 0.808(5) 0.2101(8) 0.4600(19) 0.094(2) Uiso 1.000000 GR
H10b H 0.900(2) 0.2288(13) 0.608(3) 0.094(2) Uiso 1.000000 GR
H10c H 0.733(3) 0.2526(6) 0.549(4) 0.094(2) Uiso 1.000000 GR
C11 C 0.9297(6) 0.3492(3) 0.5759(5) 0.0516(13) Uani 1.000000 .
H11a H 1.0023(6) 0.3335(3) 0.6564(5) 0.0619(16) Uiso 1.000000 R
H11b H 0.9789(6) 0.3818(3) 0.5388(5) 0.0619(16) Uiso 1.000000 R
C12 C 0.7958(5) 0.3750(2) 0.6177(5) 0.0430(11) Uani 1.000000 .
C13 C 0.6486(5) 0.3791(2) 0.5138(4) 0.0352(10) Uani 1.000000 .
C14 C 0.0337(6) 0.4104(2) 0.0609(5) 0.0469(12) Uani 1.000000 .
H14 H 0.0520(6) 0.3899(2) -0.0136(5) 0.0563(15) Uiso 1.000000 R
C15 C -0.1034(7) 0.4380(3) 0.0528(5) 0.0550(14) Uani 1.000000 .
H15 H -0.1798(7) 0.4361(3) -0.0284(5) 0.0660(17) Uiso 1.000000 R
C16 C 0.2457(5) 0.4468(2) 0.4258(4) 0.0372(10) Uani 1.000000 .
C17 C 0.3830(5) 0.4135(2) 0.4228(4) 0.0330(9) Uani 1.000000 .
C18 C 0.5163(5) 0.4105(2) 0.5497(4) 0.0318(9) Uani 1.000000 .
H18 H 0.5471(5) 0.4524(2) 0.5779(4) 0.0381(11) Uiso 1.000000 R
C19 C 0.4696(5) 0.3792(2) 0.6670(4) 0.0322(9) Uani 1.000000 .
C20 C 0.4705(5) 0.4088(2) 0.7894(4) 0.0379(10) Uani 1.000000 .
C21 C 0.4226(7) 0.3798(3) 0.8923(5) 0.0541(14) Uani 1.000000 .
H21 H 0.4230(7) 0.4007(3) 0.9723(5) 0.0650(17) Uiso 1.000000 R
C22 C 0.3750(8) 0.3208(3) 0.8763(6) 0.0647(17) Uani 1.000000 .
H22 H 0.3427(8) 0.3014(3) 0.9454(6) 0.078(2) Uiso 1.000000 R
C23 C 0.3745(7) 0.2897(3) 0.7582(7) 0.0632(16) Uani 1.000000 .
H23 H 0.3421(7) 0.2494(3) 0.7473(7) 0.0758(19) Uiso 1.000000 R
C24 C 0.4230(6) 0.3192(2) 0.6549(5) 0.0450(11) Uani 1.000000 .
H24 H 0.4239(6) 0.2977(2) 0.5758(5) 0.0539(14) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C5 O1 C4 117.2(3) . . ?
C6 O2 C5 117.1(3) . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
C2 C1 H1a 109.5 . . ?
C2 C1 H1b 109.5 . . ?
C2 C1 H1c 109.5 . . ?
C3 C2 C1 109.3(4) . . ?
C10 C2 C1 108.7(5) . . ?
C10 C2 C3 110.2(4) . . ?
C11 C2 C1 109.8(4) . . ?
C11 C2 C3 107.3(4) . . ?
C11 C2 C10 111.5(4) . . ?
H3a C3 C2 109.2(3) . . ?
H3b C3 C2 109.2(3) . . ?
H3b C3 H3a 107.9 . . ?
C4 C3 C2 111.9(3) . . ?
C4 C3 H3a 109.2(3) . . ?
C4 C3 H3b 109.2(3) . . ?
C3 C4 O1 110.5(3) . . ?
C13 C4 O1 122.2(4) . . ?
C13 C4 C3 127.3(4) . . ?
O2 C5 O1 106.3(3) . . ?
C17 C5 O1 126.4(4) . . ?
C17 C5 O2 127.3(4) . . ?
C7 C6 O2 121.6(4) . . ?
C14 C6 O2 115.4(4) . . ?
C14 C6 C7 122.9(4) . . ?
C8 C7 C6 117.8(4) . . ?
C16 C7 C6 120.3(4) . . ?
C16 C7 C8 121.9(4) . . ?
H8 C8 C7 119.8(3) . . ?
C9 C8 C7 120.3(5) . . ?
C9 C8 H8 119.8(3) . . ?
H9 C9 C8 119.8(3) . . ?
C15 C9 C8 120.3(5) . . ?
C15 C9 H9 119.8(3) . . ?
H10a C10 C2 109.5 . . ?
H10b C10 C2 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C2 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H11a C11 C2 108.8(3) . . ?
H11b C11 C2 108.8(3) . . ?
H11b C11 H11a 107.7 . . ?
C12 C11 C2 113.7(4) . . ?
C12 C11 H11a 108.8(3) . . ?
C12 C11 H11b 108.8(3) . . ?
C11 C12 O3 121.5(4) . . ?
C13 C12 O3 120.1(4) . . ?
C13 C12 C11 118.3(4) . . ?
C12 C13 C4 116.7(4) . . ?
C18 C13 C4 124.0(4) . . ?
C18 C13 C12 119.2(4) . . ?
H14 C14 C6 121.1(3) . . ?
C15 C14 C6 117.7(5) . . ?
C15 C14 H14 121.1(3) . . ?
C14 C15 C9 120.8(5) . . ?
H15 C15 C9 119.6(3) . . ?
H15 C15 C14 119.6(3) . . ?
C7 C16 O4 123.1(4) . . ?
C17 C16 O4 121.9(4) . . ?
C17 C16 C7 114.9(4) . . ?
C16 C17 C5 118.7(4) . . ?
C18 C17 C5 120.9(4) . . ?
C18 C17 C16 120.3(4) . . ?
C17 C18 C13 109.1(3) . . ?
H18 C18 C13 108.1(2) . . ?
H18 C18 C17 108.1(2) . . ?
C19 C18 C13 112.5(3) . . ?
C19 C18 C17 110.7(3) . . ?
C19 C18 H18 108.1(2) . . ?
C20 C19 C18 122.9(4) . . ?
C24 C19 C18 120.2(4) . . ?
C24 C19 C20 116.9(4) . . ?
C19 C20 Cl1 121.5(3) . . ?
C21 C20 Cl1 116.8(4) . . ?
C21 C20 C19 121.7(5) . . ?
H21 C21 C20 120.0(3) . . ?
C22 C21 C20 119.9(5) . . ?
C22 C21 H21 120.0(3) . . ?
H22 C22 C21 119.9(3) . . ?
C23 C22 C21 120.2(5) . . ?
C23 C22 H22 119.9(4) . . ?
H23 C23 C22 120.2(3) . . ?
C24 C23 C22 119.6(5) . . ?
C24 C23 H23 120.2(3) . . ?
C23 C24 C19 121.7(5) . . ?
H24 C24 C19 119.2(3) . . ?
H24 C24 C23 119.2(3) . . ?
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
Cl1 C20 1.735(5) . ?
O1 C4 1.387(5) . ?
O1 C5 1.348(5) . ?
O2 C5 1.341(5) . ?
O2 C6 1.395(5) . ?
O3 C12 1.224(6) . ?
O4 C16 1.225(5) . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C1 C2 1.523(7) . ?
C2 C3 1.530(6) . ?
C2 C10 1.518(8) . ?
C2 C11 1.536(7) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C3 C4 1.490(6) . ?
C4 C13 1.344(6) . ?
C5 C17 1.339(6) . ?
C6 C7 1.377(6) . ?
C6 C14 1.396(6) . ?
C7 C8 1.396(7) . ?
C7 C16 1.480(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(7) . ?
C9 H9 0.9300 . ?
C9 C15 1.391(8) . ?
C10 H10a 0.9600 . ?
C10 H10b 0.9600 . ?
C10 H10c 0.9600 . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C11 C12 1.501(7) . ?
C12 C13 1.477(6) . ?
C13 C18 1.512(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.455(6) . ?
C17 C18 1.523(5) . ?
C18 H18 0.9800 . ?
C18 C19 1.525(6) . ?
C19 C20 1.398(6) . ?
C19 C24 1.378(7) . ?
C20 C21 1.384(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.360(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(9) . ?
C23 H23 0.9300 . ?
C23 C24 1.394(8) . ?
C24 H24 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
Cl1 C20 C19 C18 -1.5(5) . . . . ?
Cl1 C20 C19 C24 178.9(4) . . . . ?
Cl1 C20 C21 C22 -179.8(5) . . . . ?
O1 C4 C3 C2 -158.1(4) . . . . ?
O1 C4 C13 C12 -178.2(4) . . . . ?
O1 C4 C13 C18 0.6(5) . . . . ?
O1 C5 O2 C6 -179.4(3) . . . . ?
O1 C5 C17 C16 176.0(5) . . . . ?
O1 C5 C17 C18 -2.2(6) . . . . ?
O2 C5 C17 C16 -2.3(6) . . . . ?
O2 C5 C17 C18 179.5(4) . . . . ?
O2 C6 C7 C8 179.7(4) . . . . ?
O2 C6 C7 C16 -1.5(5) . . . . ?
O2 C6 C14 C15 -179.7(5) . . . . ?
O3 C12 C11 C2 147.2(6) . . . . ?
O3 C12 C13 C4 -177.2(5) . . . . ?
O3 C12 C13 C18 3.9(6) . . . . ?
O4 C16 C7 C6 176.8(5) . . . . ?
O4 C16 C7 C8 -4.5(6) . . . . ?
O4 C16 C17 C5 -175.0(5) . . . . ?
O4 C16 C17 C18 3.2(6) . . . . ?
C1 C2 C3 C4 -167.3(5) . . . . ?
C1 C2 C11 C12 174.3(5) . . . . ?
C2 C3 C4 C13 22.4(6) . . . . ?
C2 C11 C12 C13 -34.8(6) . . . . ?
C3 C4 C13 C12 1.4(6) . . . . ?
C3 C4 C13 C18 -179.9(5) . . . . ?
C4 C13 C12 C11 4.8(5) . . . . ?
C4 C13 C18 C17 -3.5(5) . . . . ?
C4 C13 C18 C19 119.7(5) . . . . ?
C5 C17 C16 C7 3.3(5) . . . . ?
C5 C17 C18 C13 4.2(5) . . . . ?
C5 C17 C18 C19 -120.1(4) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
C6 C7 C16 C17 -1.5(5) . . . . ?
C6 C14 C15 C9 0.3(6) . . . . ?
C7 C8 C9 C15 -0.0(6) . . . . ?
C7 C16 C17 C18 -178.4(4) . . . . ?
C8 C9 C15 C14 0.1(7) . . . . ?
C11 C12 C13 C18 -174.1(5) . . . . ?
C12 C13 C18 C17 175.2(4) . . . . ?
C12 C13 C18 C19 -61.5(5) . . . . ?
C13 C18 C17 C16 -174.0(4) . . . . ?
C13 C18 C19 C20 120.7(4) . . . . ?
C13 C18 C19 C24 -59.7(4) . . . . ?
C16 C17 C18 C19 61.7(4) . . . . ?
C17 C18 C19 C20 -117.0(4) . . . . ?
C17 C18 C19 C24 62.6(4) . . . . ?
C18 C19 C20 C21 177.7(4) . . . . ?
C18 C19 C24 C23 -177.7(5) . . . . ?
C19 C20 C21 C22 0.9(6) . . . . ?
C19 C24 C23 C22 -0.9(6) . . . . ?
C20 C21 C22 C23 0.1(7) . . . . ?
C21 C22 C23 C24 -0.1(7) . . . . ?
