#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:31:31 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261766 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157826.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_7157826
loop_
_publ_author_name
'Zhao, Bin'
'Xu, Bo'
_publ_section_title
;
 Visible-light promoted oxidative cyclization of cinnamic acid derivatives
 using xanthone as the photocatalyst.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              568
_journal_page_last               573
_journal_paper_doi               10.1039/d0ob02417a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C20 H14 Cl2 O4'
_chemical_formula_weight         389.21
_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-2018/3
_audit_update_record
;
2019-08-06 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                71.5840(10)
_cell_angle_beta                 72.7130(10)
_cell_angle_gamma                72.0840(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4191(2)
_cell_length_b                   10.2779(2)
_cell_length_c                   11.5069(3)
_cell_measurement_reflns_used    7248
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      60.40
_cell_measurement_theta_min      4.93
_cell_volume                     876.57(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10859
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        52.995
_diffrn_reflns_theta_max         52.995
_diffrn_reflns_theta_min         4.925
_exptl_absorpt_coefficient_mu    2.338
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0364
_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)+(0.0547P)²+0.3277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1056
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2669
_reflns_number_total             3029
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob02417a2.cif
_cod_data_source_block           20190627ZH_ZNZ4668_0m_a
_cod_depositor_comments          'Adding full bibliography for 7157826.cif.'
_cod_database_code               7157826
_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_min   0.706
_shelx_estimated_absorpt_t_max   0.783
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 0.6208(3) 0.9544(3) 0.11182(19) 0.0562(6) Uani 1 1 d . . . . .
H1A H 0.709382 0.875337 0.084951 0.084 Uiso 1 1 calc R U . . .
H1B H 0.622376 1.039854 0.043012 0.084 Uiso 1 1 calc R U . . .
H1C H 0.508383 0.932627 0.134495 0.084 Uiso 1 1 calc R U . . .
C2 C 0.6501(2) 0.86770(19) 0.32048(17) 0.0368(4) Uani 1 1 d . . . . .
C3 C 0.6968(2) 0.89258(18) 0.42503(16) 0.0330(4) Uani 1 1 d . . . . .
C4 C 0.7253(2) 1.01986(18) 0.41692(17) 0.0350(4) Uani 1 1 d . . . . .
H4 H 0.715148 1.093564 0.342888 0.042 Uiso 1 1 calc R U . . .
C5 C 0.7692(2) 1.04337(17) 0.51609(17) 0.0342(4) Uani 1 1 d . . . . .
C6 C 0.8012(2) 1.17435(18) 0.5078(2) 0.0402(4) Uani 1 1 d . . . . .
H6 H 0.791516 1.248201 0.433767 0.048 Uiso 1 1 calc R U . . .
C7 C 0.8452(2) 1.19629(19) 0.6033(2) 0.0427(5) Uani 1 1 d . . . . .
H7 H 0.866820 1.284183 0.596315 0.051 Uiso 1 1 calc R U . . .
C8 C 0.8580(2) 1.0868(2) 0.71238(19) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.8318(2) 0.95742(18) 0.72547(17) 0.0366(4) Uani 1 1 d . . . . .
H9 H 0.844331 0.884937 0.799932 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7857(2) 0.93274(17) 0.62699(16) 0.0319(4) Uani 1 1 d . . . . .
C11 C 0.7575(2) 0.80009(17) 0.63423(16) 0.0307(4) Uani 1 1 d . . . . .
C12 C 0.7122(2) 0.78141(17) 0.53609(16) 0.0306(4) Uani 1 1 d . . . . .
C13 C 0.6826(2) 0.63954(17) 0.55176(15) 0.0312(4) Uani 1 1 d . . . . .
C14 C 0.4930(3) 0.4923(2) 0.66733(19) 0.0455(5) Uani 1 1 d . . . . .
H14A H 0.518013 0.453569 0.594483 0.068 Uiso 1 1 calc R U . . .
H14B H 0.372034 0.499810 0.709568 0.068 Uiso 1 1 calc R U . . .
H14C H 0.564690 0.429873 0.725871 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7838(2) 0.67897(17) 0.74598(16) 0.0316(4) Uani 1 1 d . . . . .
C16 C 0.6663(3) 0.6736(2) 0.86051(18) 0.0442(5) Uani 1 1 d . . . . .
H16 H 0.567995 0.749246 0.869083 0.053 Uiso 1 1 calc R U . . .
C17 C 0.6907(3) 0.5597(2) 0.96205(19) 0.0521(5) Uani 1 1 d . . . . .
H17 H 0.609744 0.556630 1.040047 0.063 Uiso 1 1 calc R U . . .
C18 C 0.8338(3) 0.4504(2) 0.94889(18) 0.0457(5) Uani 1 1 d . . . . .
C19 C 0.9524(3) 0.45299(19) 0.83703(19) 0.0435(5) Uani 1 1 d . . . . .
H19 H 1.050886 0.377370 0.829285 0.052 Uiso 1 1 calc R U . . .
C20 C 0.9265(2) 0.56755(18) 0.73551(17) 0.0370(4) Uani 1 1 d . . . . .
H20 H 1.007583 0.569751 0.657668 0.044 Uiso 1 1 calc R U . . .
Cl1 Cl 0.90901(8) 1.11802(6) 0.83432(5) 0.0597(2) Uani 1 1 d . . . . .
Cl2 Cl 0.86135(10) 0.30361(6) 1.07529(5) 0.0716(2) Uani 1 1 d . . . . .
O1 O 0.65358(18) 0.97684(15) 0.21917(12) 0.0482(4) Uani 1 1 d . . . . .
O2 O 0.6141(2) 0.76275(15) 0.32415(13) 0.0556(4) Uani 1 1 d . . . . .
O3 O 0.78490(17) 0.54464(13) 0.51203(13) 0.0431(3) Uani 1 1 d . . . . .
O4 O 0.52862(15) 0.63035(12) 0.62624(11) 0.0352(3) 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 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 122.81(17) . . ?
O2 C2 C3 124.71(16) . . ?
O1 C2 C3 112.48(15) . . ?
C4 C3 C12 119.54(16) . . ?
C4 C3 C2 121.31(16) . . ?
C12 C3 C2 119.15(15) . . ?
C3 C4 C5 121.26(16) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 121.60(17) . . ?
C4 C5 C10 119.55(15) . . ?
C6 C5 C10 118.84(17) . . ?
C7 C6 C5 121.46(18) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 118.78(16) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 122.63(18) . . ?
C9 C8 Cl1 119.24(16) . . ?
C7 C8 Cl1 118.13(14) . . ?
C8 C9 C10 119.35(17) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C5 118.92(15) . . ?
C9 C10 C11 122.21(16) . . ?
C5 C10 C11 118.86(16) . . ?
C12 C11 C10 120.04(15) . . ?
C12 C11 C15 119.62(14) . . ?
C10 C11 C15 120.30(15) . . ?
C11 C12 C3 120.73(15) . . ?
C11 C12 C13 116.74(15) . . ?
C3 C12 C13 122.52(15) . . ?
O3 C13 O4 124.53(15) . . ?
O3 C13 C12 125.72(16) . . ?
O4 C13 C12 109.53(14) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.68(17) . . ?
C20 C15 C11 119.80(15) . . ?
C16 C15 C11 121.51(16) . . ?
C17 C16 C15 120.79(19) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.25(19) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C19 C18 C17 121.25(18) . . ?
C19 C18 Cl2 119.34(17) . . ?
C17 C18 Cl2 119.37(16) . . ?
C18 C19 C20 119.06(19) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C15 C20 C19 120.97(17) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C2 O1 C1 114.75(16) . . ?
C13 O4 C14 116.02(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
C1 O1 1.441(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.192(2) . ?
C2 O1 1.339(2) . ?
C2 C3 1.485(3) . ?
C3 C4 1.371(2) . ?
C3 C12 1.428(2) . ?
C4 C5 1.406(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.421(2) . ?
C5 C10 1.425(2) . ?
C6 C7 1.359(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.369(2) . ?
C8 Cl1 1.727(2) . ?
C9 C10 1.415(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.428(2) . ?
C11 C12 1.377(2) . ?
C11 C15 1.497(2) . ?
C12 C13 1.500(2) . ?
C13 O3 1.197(2) . ?
C13 O4 1.337(2) . ?
C14 O4 1.442(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.387(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.373(3) . ?
C18 Cl2 1.7447(19) . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
