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#$Date: 2022-07-04 12:27:05 +0300 (Mon, 04 Jul 2022) $
#$Revision: 276534 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105634.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_8105634
loop_
_publ_author_name
'Yun-Lian, Shi'
'Tao, Huang'
'Xu-Liang, Nie'
'Da-Yong, Peng'
'Jin-Chuan, Liu'
'Bao-Tong, Li'
_publ_section_title
;
 Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              331
_journal_page_last               332
_journal_paper_doi               10.1515/ncrs-2018-0394
_journal_volume                  234
_journal_year                    2019
_chemical_formula_sum            'C15 H6 Cl6 O4'
_chemical_formula_weight         462.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.2310(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0980(11)
_cell_length_b                   10.0628(9)
_cell_length_c                   15.1518(14)
_cell_measurement_reflns_used    5576
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.67
_cell_volume                     1788.0(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_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_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6761
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.478
_diffrn_reflns_theta_min         2.667
_exptl_absorpt_coefficient_mu    0.996
_exptl_crystal_colour            clorless
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1283 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(18)
_refine_ls_extinction_coef       0.0071(6)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0214
_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)+(0.0309P)²+0.5884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0568
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.815
_reflns_number_gt                2952
_reflns_number_total             3023
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0394_suppl.cif
_cod_data_source_block           3619_0m
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               8105634
_shelx_shelxl_version_number     2014/7
_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   0.857
_shelx_estimated_absorpt_t_max   0.890
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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_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 0.4028(2) 0.7439(3) 0.7211(2) 0.0404(6) Uani 1 1 d . . . . .
C2 C 0.3300(2) 0.6358(3) 0.7001(2) 0.0447(6) Uani 1 1 d . . . . .
C3 C 0.3337(3) 0.5341(3) 0.7616(2) 0.0492(7) Uani 1 1 d . . . . .
H3 H 0.2842 0.4621 0.7478 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4131(3) 0.5419(3) 0.8445(2) 0.0488(7) Uani 1 1 d . . . . .
C5 C 0.4875(3) 0.6471(3) 0.8675(2) 0.0461(7) Uani 1 1 d . . . . .
H5 H 0.5403 0.6504 0.9236 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4809(2) 0.7476(3) 0.8043(2) 0.0418(6) Uani 1 1 d . . . . .
C7 C 0.4609(2) 0.8445(3) 0.6012(2) 0.0409(6) Uani 1 1 d . . . . .
C8 C 0.4453(3) 0.9649(3) 0.5412(2) 0.0512(7) Uani 1 1 d . . . . .
H8A H 0.4608 1.0433 0.5794 0.061 Uiso 1 1 calc R U . . .
H8B H 0.5012 0.9621 0.5049 0.061 Uiso 1 1 calc R U . . .
C9 C 0.3289(2) 0.9783(3) 0.4783(2) 0.0507(8) Uani 1 1 d . . . . .
C10 C 0.2370(2) 1.0893(3) 0.3437(2) 0.0424(6) Uani 1 1 d . . . . .
C11 C 0.1700(2) 1.1991(3) 0.3461(2) 0.0425(6) Uani 1 1 d . . . . .
C12 C 0.0793(2) 1.2288(3) 0.2735(2) 0.0417(6) Uani 1 1 d . . . . .
H12 H 0.0345 1.3036 0.2747 0.050 Uiso 1 1 calc R U . . .
C13 C 0.0568(2) 1.1451(3) 0.19938(19) 0.0410(6) Uani 1 1 d . . . . .
C14 C 0.1216(3) 1.0341(3) 0.1951(2) 0.0463(7) Uani 1 1 d . . . . .
H14 H 0.1049 0.9785 0.1445 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2121(2) 1.0079(3) 0.2683(2) 0.0475(7) Uani 1 1 d . . . . .
O1 O 0.39339(17) 0.8502(2) 0.66100(15) 0.0474(5) Uani 1 1 d . . . . .
O2 O 0.5245(2) 0.7569(3) 0.59956(17) 0.0664(7) Uani 1 1 d . . . . .
O3 O 0.2442(2) 0.9227(4) 0.4817(2) 0.0933(11) Uani 1 1 d . . . . .
O4 O 0.33483(17) 1.0684(2) 0.41368(16) 0.0538(6) Uani 1 1 d . . . . .
Cl1 Cl 0.23312(8) 0.62950(10) 0.59519(6) 0.0650(2) Uani 1 1 d . . . . .
Cl2 Cl 0.57314(7) 0.88156(8) 0.83113(6) 0.0610(2) Uani 1 1 d . . . . .
Cl3 Cl 0.42004(10) 0.41507(9) 0.92305(7) 0.0733(3) Uani 1 1 d . . . . .
Cl4 Cl 0.19913(7) 1.30229(10) 0.44010(6) 0.0663(3) Uani 1 1 d . . . . .
Cl5 Cl -0.05775(7) 1.18000(8) 0.10804(6) 0.0606(2) Uani 1 1 d . . . . .
Cl6 Cl 0.29540(9) 0.86970(9) 0.26502(10) 0.0843(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 0.0033 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'
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'
Cl Cl 0.1484 0.1585 '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
C6 C1 O1 120.4(2) . .
C6 C1 C2 119.0(3) . .
O1 C1 C2 120.5(3) . .
C3 C2 C1 121.0(3) . .
C3 C2 Cl1 119.8(2) . .
C1 C2 Cl1 119.2(2) . .
C2 C3 C4 118.2(3) . .
C5 C4 C3 122.5(3) . .
C5 C4 Cl3 118.3(2) . .
C3 C4 Cl3 119.2(2) . .
C4 C5 C6 117.7(3) . .
C1 C6 C5 121.6(3) . .
C1 C6 Cl2 119.5(2) . .
C5 C6 Cl2 118.8(2) . .
O2 C7 O1 123.2(3) . .
O2 C7 C8 125.5(3) . .
O1 C7 C8 111.3(3) . .
C9 C8 C7 114.7(2) . .
O3 C9 O4 123.5(3) . .
O3 C9 C8 128.3(3) . .
O4 C9 C8 108.2(2) . .
C11 C10 C15 119.2(3) . .
C11 C10 O4 119.7(3) . .
C15 C10 O4 120.8(3) . .
C10 C11 C12 120.7(3) . .
C10 C11 Cl4 120.1(2) . .
C12 C11 Cl4 119.1(2) . .
C13 C12 C11 118.4(3) . .
C14 C13 C12 122.3(3) . .
C14 C13 Cl5 118.6(2) . .
C12 C13 Cl5 119.0(2) . .
C13 C14 C15 117.8(3) . .
C14 C15 C10 121.5(3) . .
C14 C15 Cl6 119.0(3) . .
C10 C15 Cl6 119.5(2) . .
C7 O1 C1 115.9(2) . .
C9 O4 C10 117.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.376(4) .
C1 O1 1.392(3) .
C1 C2 1.387(4) .
C2 C3 1.377(4) .
C2 Cl1 1.729(3) .
C3 C4 1.383(5) .
C4 C5 1.378(5) .
C4 Cl3 1.732(3) .
C5 C6 1.381(4) .
C6 Cl2 1.734(3) .
C7 O2 1.174(4) .
C7 O1 1.363(4) .
C7 C8 1.498(4) .
C8 C9 1.499(4) .
C9 O3 1.181(4) .
C9 O4 1.349(4) .
C10 C11 1.376(4) .
C10 C15 1.378(5) .
C10 O4 1.397(3) .
C11 C12 1.382(4) .
C11 Cl4 1.728(3) .
C12 C13 1.377(4) .
C13 C14 1.375(4) .
C13 Cl5 1.737(3) .
C14 C15 1.379(4) .
C15 Cl6 1.725(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14 O2 0.93 2.59 3.348(4) 139.4 4_464
C12 H12 Cl6 0.93 2.94 3.688(3) 138.9 3_455
C8 H8A Cl5 0.97 2.83 3.717(3) 151.7 4_575
C5 H5 O3 0.93 2.52 3.239(4) 134.8 4_565
