#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:58:01 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225244 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156788.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_7156788
loop_
_publ_author_name
'Kong, Hongjun'
'Li, Qingrui'
'Yin, Yunnian'
'Huang, Mengmeng'
'Kim, Jung Keun'
'Zhu, Yu'
'Li, Yabo'
'Wu, Yangjie'
_publ_section_title
;
 An efficient light on-off one-pot method for the synthesis of 3-styryl
 coumarins from aryl alkynoates.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4621
_journal_page_last               4628
_journal_paper_doi               10.1039/c9ob00421a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C24 H17 Cl O2'
_chemical_formula_sum            'C24 H17 Cl O2'
_chemical_formula_weight         372.82
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-08 deposited with the CCDC.    2019-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6928(4)
_cell_length_b                   7.0340(3)
_cell_length_c                   21.7643(8)
_cell_measurement_reflns_used    1090
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1460
_cell_measurement_theta_min      4.0160
_cell_volume                     1943.14(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   33.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   60.0000 164

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00  -22.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   36.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00   82.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
  5 omega   60.00   88.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega   76.00  106.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00  104.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 130

#__ type_ start__ end____ width___ exp.time_
  8 omega   54.00  107.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 106

#__ type_ start__ end____ width___ exp.time_
  9 omega   54.00   80.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   62.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00  169.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -120.0000 262
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1064366000
_diffrn_orient_matrix_UB_12      -0.0495235000
_diffrn_orient_matrix_UB_13      -0.0300128000
_diffrn_orient_matrix_UB_21      -0.0386947000
_diffrn_orient_matrix_UB_22      0.0846571000
_diffrn_orient_matrix_UB_23      -0.0612662000
_diffrn_orient_matrix_UB_31      0.0436408000
_diffrn_orient_matrix_UB_32      0.1958040000
_diffrn_orient_matrix_UB_33      0.0189016000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4210
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.032
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.0013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1890
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.214
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0728
_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)+(0.1336P)²+0.3204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1302
_reflns_number_total             1890
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ob00421a2.cif
_cod_data_source_block           201809371
_cod_depositor_comments
'Adding full bibliography for 7156785--7156790.cif.'
_cod_original_cell_volume        1943.16(13)
_cod_database_code               7156788
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N4Cl1
_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   0.836
_shelx_estimated_absorpt_t_min   0.644
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C6-C5
 1.4 with sigma of 0.02
 C6-C1
 1.4 with sigma of 0.02
 C5-C4
 1.4 with sigma of 0.02
 C4-C3
 1.5 with sigma of 0.02
 C2-C1
 1.4 with sigma of 0.02
 C3-C2
 1.6 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: H18A(0.5) H18B(0.5) H18C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C16(H16),
 C17(H17), C20(H20), C21(H21)
5.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'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 0.1668(6) 0.2500 0.2650(2) 0.117(2) Uani 1 2 d DS TU P . .
H1 H 0.0946 0.2500 0.2576 0.140 Uiso 1 2 calc RS T P . .
C2 C 0.2341(7) 0.2500 0.2149(3) 0.125(2) Uani 1 2 d DS TU P . .
H2 H 0.2073 0.2500 0.1752 0.150 Uiso 1 2 calc RS T P . .
C3 C 0.3399(8) 0.2500 0.2246(3) 0.151(3) Uani 1 2 d DS TU P . .
H3 H 0.3872 0.2500 0.1920 0.182 Uiso 1 2 calc RS T P . .
C4 C 0.3744(9) 0.2500 0.2844(4) 0.204(4) Uani 1 2 d DS TU P . .
H4 H 0.4465 0.2500 0.2921 0.245 Uiso 1 2 calc RS T P . .
C5 C 0.3059(6) 0.2500 0.3333(3) 0.157(3) Uani 1 2 d DS TU P . .
H5 H 0.3322 0.2500 0.3732 0.188 Uiso 1 2 calc RS T P . .
C6 C 0.1998(4) 0.2500 0.32403(19) 0.0845(13) Uani 1 2 d DS TU P . .
C7 C 0.1241(4) 0.2500 0.37431(19) 0.0764(11) Uani 1 2 d S T P . .
H7 H 0.0533 0.2500 0.3635 0.092 Uiso 1 2 calc RS T P . .
C8 C 0.1454(3) 0.2500 0.43280(16) 0.0665(10) Uani 1 2 d S T P . .
H8 H 0.2170 0.2500 0.4420 0.080 Uiso 1 2 calc RS T P . .
C9 C -0.0389(3) 0.2500 0.47813(16) 0.0592(9) Uani 1 2 d S T P . .
C10 C 0.0767(3) 0.2500 0.48629(14) 0.0534(8) Uani 1 2 d S T P . .
C11 C 0.1167(3) 0.2500 0.54469(16) 0.0586(9) Uani 1 2 d S T P . .
C12 C 0.0481(3) 0.2500 0.59719(16) 0.0606(9) Uani 1 2 d S T P . .
C13 C -0.0597(3) 0.2500 0.58784(16) 0.0570(8) Uani 1 2 d S T P . .
C14 C -0.1310(3) 0.2500 0.6365(2) 0.0723(11) Uani 1 2 d S T P . .
H14 H -0.2029 0.2500 0.6285 0.087 Uiso 1 2 calc RS T P . .
C15 C -0.0964(4) 0.2500 0.6958(2) 0.0813(12) Uani 1 2 d S T P . .
C16 C 0.0112(4) 0.2500 0.7060(2) 0.0979(16) Uani 1 2 d S T P . .
H16 H 0.0361 0.2500 0.7462 0.117 Uiso 1 2 calc RS T P . .
C17 C 0.0821(4) 0.2500 0.65843(19) 0.0868(14) Uani 1 2 d S T P . .
H17 H 0.1539 0.2500 0.6670 0.104 Uiso 1 2 calc RS T P . .
C18 C -0.1726(5) 0.2500 0.7482(3) 0.116(2) Uani 1 2 d S T P . .
H18A H -0.2344 0.1796 0.7370 0.175 Uiso 0.5 1 calc GR . . A -1
H18B H -0.1919 0.3785 0.7580 0.175 Uiso 0.5 1 calc GR . . A -1
H18C H -0.1403 0.1919 0.7834 0.175 Uiso 0.5 1 calc GR . . A -1
C19 C 0.2334(3) 0.2500 0.55504(16) 0.0668(10) Uani 1 2 d S T P . .
C20 C 0.2879(3) 0.4141(7) 0.5597(2) 0.1045(13) Uani 1 1 d . . . . .
H20 H 0.2518 0.5289 0.5567 0.125 Uiso 1 1 calc R . . . .
C21 C 0.3965(3) 0.4167(8) 0.5686(2) 0.1210(16) Uani 1 1 d . . . . .
H21 H 0.4329 0.5311 0.5713 0.145 Uiso 1 1 calc R . . . .
C22 C 0.4473(4) 0.2500 0.5734(3) 0.1055(19) Uani 1 2 d S T P . .
Cl1 Cl 0.58328(11) 0.2500 0.58469(14) 0.1863(13) Uani 1 2 d S T P . .
O1 O -0.0854(2) 0.2500 0.43058(12) 0.0785(9) Uani 1 2 d S T P . .
O2 O -0.10079(18) 0.2500 0.52985(12) 0.0659(7) Uani 1 2 d S T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 118.1 . .
C6 C1 H1 118.1 . .
C6 C1 C2 123.9(7) . .
C1 C2 H2 120.4 . .
C3 C2 C1 119.2(6) . .
C3 C2 H2 120.4 . .
C2 C3 H3 121.2 . .
C2 C3 C4 117.5(7) . .
C4 C3 H3 121.2 . .
C3 C4 H4 118.9 . .
C3 C4 C5 122.2(10) . .
C5 C4 H4 118.9 . .
C4 C5 H5 119.7 . .
C6 C5 C4 120.7(8) . .
C6 C5 H5 119.7 . .
C1 C6 C5 116.6(5) . .
C1 C6 C7 120.7(5) . .
C5 C6 C7 122.7(5) . .
C6 C7 H7 116.6 . .
C8 C7 C6 126.8(5) . .
C8 C7 H7 116.6 . .
C7 C8 H8 114.4 . .
C7 C8 C10 131.2(4) . .
C10 C8 H8 114.4 . .
O1 C9 C10 126.6(3) . .
O1 C9 O2 115.4(3) . .
O2 C9 C10 118.0(3) . .
C8 C10 C9 119.9(3) . .
C11 C10 C8 121.4(3) . .
C11 C10 C9 118.7(3) . .
C10 C11 C12 120.9(3) . .
C10 C11 C19 120.4(3) . .
C12 C11 C19 118.7(3) . .
C13 C12 C11 118.9(3) . .
C13 C12 C17 116.4(3) . .
C17 C12 C11 124.7(4) . .
C12 C13 C14 122.0(4) . .
O2 C13 C12 120.9(3) . .
O2 C13 C14 117.1(3) . .
C13 C14 H14 119.6 . .
C15 C14 C13 120.7(4) . .
C15 C14 H14 119.6 . .
C14 C15 C16 118.0(4) . .
C14 C15 C18 120.9(5) . .
C16 C15 C18 121.0(5) . .
C15 C16 H16 119.1 . .
C17 C16 C15 121.8(4) . .
C17 C16 H16 119.1 . .
C12 C17 H17 119.5 . .
C16 C17 C12 121.0(4) . .
C16 C17 H17 119.5 . .
C15 C18 H18A 109.5 . .
C15 C18 H18B 109.5 . .
C15 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C20 C19 C11 121.2(2) . .
C20 C19 C11 121.2(2) 8_565 .
C20 C19 C20 117.6(4) 8_565 .
C19 C20 H20 119.0 . .
C19 C20 C21 121.9(4) . .
C21 C20 H20 119.0 . .
C20 C21 H21 120.8 . .
C22 C21 C20 118.4(5) . .
C22 C21 H21 120.8 . .
C21 C22 C21 121.8(5) . 8_565
C21 C22 Cl1 119.1(2) 8_565 .
C21 C22 Cl1 119.1(2) . .
C13 O2 C9 122.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9300 .
C1 C2 1.385(8) .
C1 C6 1.351(7) .
C2 H2 0.9300 .
C2 C3 1.359(10) .
C3 H3 0.9300 .
C3 C4 1.373(11) .
C4 H4 0.9300 .
C4 C5 1.375(9) .
C5 H5 0.9300 .
C5 C6 1.362(9) .
C6 C7 1.456(6) .
C7 H7 0.9300 .
C7 C8 1.301(6) .
C8 H8 0.9300 .
C8 C10 1.455(5) .
C9 C10 1.478(5) .
C9 O1 1.191(4) .
C9 O2 1.373(4) .
C10 C11 1.369(5) .
C11 C12 1.437(5) .
C11 C19 1.498(5) .
C12 C13 1.383(5) .
C12 C17 1.401(6) .
C13 C14 1.393(5) .
C13 O2 1.365(4) .
C14 H14 0.9300 .
C14 C15 1.362(7) .
C15 C16 1.384(7) .
C15 C18 1.496(6) .
C16 H16 0.9300 .
C16 C17 1.372(7) .
C17 H17 0.9300 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 C20 1.350(5) 8_565
C19 C20 1.350(5) .
C20 H20 0.9300 .
C20 C21 1.392(5) .
C21 H21 0.9300 .
C21 C22 1.342(6) .
C22 C21 1.342(6) 8_565
C22 Cl1 1.743(5) .
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_4
C1 C2 C3 C4 0.000(1) . .
C1 C6 C7 C8 180.000(1) . .
C2 C1 C6 C5 0.000(1) . .
C2 C1 C6 C7 180.000(1) . .
C2 C3 C4 C5 0.000(1) . .
C3 C4 C5 C6 0.000(1) . .
C4 C5 C6 C1 0.000(1) . .
C4 C5 C6 C7 180.000(1) . .
C5 C6 C7 C8 0.000(1) . .
C6 C1 C2 C3 0.000(1) . .
C6 C7 C8 C10 180.000(1) . .
C7 C8 C10 C9 0.000(1) . .
C7 C8 C10 C11 180.000(1) . .
C8 C10 C11 C12 180.000(1) . .
C8 C10 C11 C19 0.000(1) . .
C9 C10 C11 C12 0.000(1) . .
C9 C10 C11 C19 180.000(1) . .
C10 C9 O2 C13 0.000(1) . .
C10 C11 C12 C13 0.000(1) . .
C10 C11 C12 C17 180.000(1) . .
C10 C11 C19 C20 89.8(4) . .
C10 C11 C19 C20 -89.8(4) . 8_565
C11 C12 C13 C14 180.000(1) . .
C11 C12 C13 O2 0.000(1) . .
C11 C12 C17 C16 180.000(1) . .
C11 C19 C20 C21 -179.3(4) . .
C12 C11 C19 C20 -90.2(4) . .
C12 C11 C19 C20 90.2(4) . 8_565
C12 C13 C14 C15 0.000(2) . .
C12 C13 O2 C9 0.000(1) . .
C13 C12 C17 C16 0.000(2) . .
C13 C14 C15 C16 0.000(2) . .
C13 C14 C15 C18 180.000(2) . .
C14 C13 O2 C9 180.000(1) . .
C14 C15 C16 C17 0.000(2) . .
C15 C16 C17 C12 0.000(2) . .
C17 C12 C13 C14 0.000(1) . .
C17 C12 C13 O2 180.000(1) . .
C18 C15 C16 C17 180.000(2) . .
C19 C11 C12 C13 180.000(1) . .
C19 C11 C12 C17 0.000(1) . .
C19 C20 C21 C22 -0.7(8) . .
C20 C19 C20 C21 0.2(8) 8_565 .
C20 C21 C22 C21 1.2(10) . 8_565
C20 C21 C22 Cl1 -180.0(4) . .
O1 C9 C10 C8 0.000(1) . .
O1 C9 C10 C11 180.000(1) . .
O1 C9 O2 C13 180.000(1) . .
O2 C9 C10 C8 180.000(1) . .
O2 C9 C10 C11 0.000(1) . .
O2 C13 C14 C15 180.000(1) . .
