#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/20/48/7204853.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_7204853
loop_
_publ_author_name
'Kumar, V. S. Senthil'
'Pigge, F. Christopher'
'Rath, Nigam P.'
_publ_section_title
;
 Polymorphism in 1,3,5-triaroylbenzenes: structural characterization of
 concomitant polymorphs obtained from
 1,3,5-tris(4-chlorobenzoyl)benzene
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              102
_journal_paper_doi               10.1039/b401894j
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         'C27 H15 Cl3 O3'
_chemical_formula_sum            'C27 H15 Cl3 O3'
_chemical_formula_weight         493.74
_chemical_melting_point          459
_chemical_name_common            1,3,5-tris(4-cholorobenzoyl)benzene
_chemical_name_systematic
;
1,3,5-tris(4-cholorobenzoyl)benzene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.955(2)
_cell_angle_beta                 97.735(2)
_cell_angle_gamma                106.980(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6385(2)
_cell_length_b                   11.1276(3)
_cell_length_c                   12.4701(3)
_cell_measurement_reflns_used    5421
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      2.4
_cell_volume                     1122.99(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker-SHELXTL (Sheldrick, 2003)'
_computing_publication_material  'Bruker-SHELXTL (Sheldrick, 2003)'
_computing_structure_refinement  'Bruker-SHELXTL (Sheldrick, 2003)'
_computing_structure_solution    'Bruker-SHELXTL (Sheldrick, 2003)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26434
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_T_max  0.9178
_exptl_absorpt_correction_T_min  0.8875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0713P)²+0.1468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                3692
_reflns_number_total             5788
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b401894j.txt
_cod_data_source_block           B
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '459 K' was changed to '459' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204853
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.01805(9) 0.11488(6) 0.71317(5) 0.0793(2) Uani 1 1 d . . .
Cl2 Cl -0.15388(8) 0.42551(8) -0.40342(5) 0.0868(2) Uani 1 1 d . . .
Cl3 Cl 0.44563(10) -0.07007(8) -0.38898(5) 0.0944(3) Uani 1 1 d . . .
O1 O 0.54178(19) 0.40658(16) 0.40587(12) 0.0733(5) Uani 1 1 d . . .
O2 O 0.39533(18) 0.59120(13) 0.05873(13) 0.0643(4) Uani 1 1 d . . .
O3 O 0.13496(19) -0.06773(13) 0.07330(12) 0.0637(4) Uani 1 1 d . . .
C1 C 0.3336(2) 0.30361(18) 0.25699(14) 0.0481(4) Uani 1 1 d . . .
C2 C 0.3363(2) 0.40193(18) 0.19716(15) 0.0487(4) Uani 1 1 d . . .
H2 H 0.3721 0.4852 0.2331 0.058 Uiso 1 1 calc R . .
C3 C 0.2863(2) 0.37816(17) 0.08403(14) 0.0452(4) Uani 1 1 d . . .
C4 C 0.2447(2) 0.25405(16) 0.02991(14) 0.0449(4) Uani 1 1 d . . .
H4 H 0.2148 0.2375 -0.0459 0.054 Uiso 1 1 calc R . .
C5 C 0.2474(2) 0.15471(17) 0.08852(14) 0.0449(4) Uani 1 1 d . . .
C6 C 0.2854(2) 0.17923(18) 0.20260(14) 0.0488(4) Uani 1 1 d . . .
H6 H 0.2785 0.1123 0.2425 0.059 Uiso 1 1 calc R . .
C7 C 0.4029(3) 0.33424(19) 0.37768(16) 0.0533(5) Uani 1 1 d . . .
C8 C 0.3035(2) 0.27667(18) 0.45802(14) 0.0494(4) Uani 1 1 d . . .
C9 C 0.1382(3) 0.2128(2) 0.42999(16) 0.0599(5) Uani 1 1 d . . .
H9 H 0.0864 0.2025 0.3578 0.072 Uiso 1 1 calc R . .
C10 C 0.0473(3) 0.1631(2) 0.50802(17) 0.0660(6) Uani 1 1 d . . .
H10 H -0.0646 0.1202 0.4888 0.079 Uiso 1 1 calc R . .
C11 C 0.1265(3) 0.17886(19) 0.61437(16) 0.0596(5) Uani 1 1 d . . .
C12 C 0.2911(3) 0.2436(2) 0.64433(16) 0.0647(6) Uani 1 1 d . . .
H12 H 0.3425 0.2544 0.7167 0.078 Uiso 1 1 calc R . .
C13 C 0.3788(3) 0.2922(2) 0.56687(16) 0.0623(5) Uani 1 1 d . . .
H13 H 0.4903 0.3362 0.5870 0.075 Uiso 1 1 calc R . .
C14 C 0.2955(2) 0.48734(17) 0.02207(16) 0.0484(4) Uani 1 1 d . . .
C15 C 0.1831(2) 0.46740(17) -0.08420(15) 0.0472(4) Uani 1 1 d . . .
C16 C 0.2396(3) 0.5317(2) -0.16836(18) 0.0602(5) Uani 1 1 d . . .
H16 H 0.3470 0.5857 -0.1576 0.072 Uiso 1 1 calc R . .
C17 C 0.1377(3) 0.5160(2) -0.26756(18) 0.0641(6) Uani 1 1 d . . .
H17 H 0.1775 0.5556 -0.3248 0.077 Uiso 1 1 calc R . .
C18 C -0.0226(3) 0.4415(2) -0.28034(17) 0.0580(5) Uani 1 1 d . . .
C19 C -0.0832(3) 0.3789(2) -0.19835(17) 0.0579(5) Uani 1 1 d . . .
H19 H -0.1929 0.3297 -0.2082 0.070 Uiso 1 1 calc R . .
C20 C 0.0210(2) 0.38978(18) -0.10072(16) 0.0525(4) Uani 1 1 d . . .
H20 H -0.0178 0.3448 -0.0459 0.063 Uiso 1 1 calc R . .
C21 C 0.2118(2) 0.02159(17) 0.03307(15) 0.0468(4) Uani 1 1 d . . .
C22 C 0.2753(2) 0.00020(16) -0.07023(14) 0.0464(4) Uani 1 1 d . . .
C23 C 0.4122(2) 0.08669(18) -0.09486(16) 0.0521(4) Uani 1 1 d . . .
H23 H 0.4672 0.1609 -0.0463 0.062 Uiso 1 1 calc R . .
C24 C 0.4675(3) 0.0630(2) -0.19166(19) 0.0628(5) Uani 1 1 d . . .
H24 H 0.5606 0.1206 -0.2076 0.075 Uiso 1 1 calc R . .
C25 C 0.3841(3) -0.0460(2) -0.26425(17) 0.0616(5) Uani 1 1 d . . .
C26 C 0.2517(3) -0.1346(2) -0.23930(18) 0.0644(6) Uani 1 1 d . . .
H26 H 0.1984 -0.2092 -0.2878 0.077 Uiso 1 1 calc R . .
C27 C 0.1975(3) -0.11306(19) -0.14206(17) 0.0573(5) Uani 1 1 d . . .
H27 H 0.1092 -0.1740 -0.1243 0.069 Uiso 1 1 calc R . .
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'
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
_geom_angle_publ_flag
C2 C1 C6 119.38(16) . . ?
C2 C1 C7 119.25(17) . . ?
C6 C1 C7 120.92(17) . . ?
C1 C2 C3 121.05(17) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 119.06(16) . . ?
C2 C3 C14 119.36(16) . . ?
C4 C3 C14 121.26(16) . . ?
C5 C4 C3 120.46(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.49(16) . . ?
C4 C5 C21 122.01(15) . . ?
C6 C5 C21 118.50(16) . . ?
C1 C6 C5 120.27(16) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O1 C7 C8 121.83(18) . . ?
O1 C7 C1 117.74(18) . . ?
C8 C7 C1 120.43(17) . . ?
C9 C8 C13 118.73(19) . . ?
C9 C8 C7 122.34(17) . . ?
C13 C8 C7 118.88(18) . . ?
C8 C9 C10 120.94(19) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 118.6(2) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C12 C11 C10 121.36(19) . . ?
C12 C11 Cl1 118.79(16) . . ?
C10 C11 Cl1 119.85(18) . . ?
C13 C12 C11 119.39(19) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C8 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
O2 C14 C15 120.89(17) . . ?
O2 C14 C3 119.79(17) . . ?
C15 C14 C3 119.32(15) . . ?
C20 C15 C16 118.81(18) . . ?
C20 C15 C14 121.79(16) . . ?
C16 C15 C14 119.37(17) . . ?
C17 C16 C15 120.72(19) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.04(19) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 121.70(19) . . ?
C17 C18 Cl2 119.41(17) . . ?
C19 C18 Cl2 118.89(17) . . ?
C18 C19 C20 119.22(19) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C15 120.42(18) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
O3 C21 C22 120.90(16) . . ?
O3 C21 C5 120.25(16) . . ?
C22 C21 C5 118.83(15) . . ?
C23 C22 C27 119.24(18) . . ?
C23 C22 C21 121.99(16) . . ?
C27 C22 C21 118.72(17) . . ?
C22 C23 C24 120.19(19) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 120.71(19) . . ?
C26 C25 Cl3 119.73(18) . . ?
C24 C25 Cl3 119.56(18) . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C22 120.1(2) . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
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 C11 1.734(2) . ?
Cl2 C18 1.741(2) . ?
Cl3 C25 1.730(2) . ?
O1 C7 1.214(2) . ?
O2 C14 1.221(2) . ?
O3 C21 1.220(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.507(3) . ?
C2 C3 1.392(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(2) . ?
C3 C14 1.495(3) . ?
C4 C5 1.391(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(2) . ?
C5 C21 1.494(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.481(3) . ?
C8 C9 1.374(3) . ?
C8 C13 1.394(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(3) . ?
C12 C13 1.365(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.488(3) . ?
C15 C20 1.389(3) . ?
C15 C16 1.393(3) . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.490(3) . ?
C22 C23 1.383(3) . ?
C22 C27 1.397(3) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.371(3) . ?
C26 C27 1.380(3) . ?
C26 H26 0.9300 . ?
C27 H27 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
C6 C1 C2 C3 2.2(3) . . . . ?
C7 C1 C2 C3 174.56(17) . . . . ?
C1 C2 C3 C4 -4.8(3) . . . . ?
C1 C2 C3 C14 -178.32(17) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C14 C3 C4 C5 175.66(17) . . . . ?
C3 C4 C5 C6 2.8(3) . . . . ?
C3 C4 C5 C21 -176.86(16) . . . . ?
C2 C1 C6 C5 2.9(3) . . . . ?
C7 C1 C6 C5 -169.32(18) . . . . ?
C4 C5 C6 C1 -5.4(3) . . . . ?
C21 C5 C6 C1 174.28(17) . . . . ?
C2 C1 C7 O1 -53.0(3) . . . . ?
C6 C1 C7 O1 119.3(2) . . . . ?
C2 C1 C7 C8 127.3(2) . . . . ?
C6 C1 C7 C8 -60.4(3) . . . . ?
O1 C7 C8 C9 168.5(2) . . . . ?
C1 C7 C8 C9 -11.8(3) . . . . ?
O1 C7 C8 C13 -8.8(3) . . . . ?
C1 C7 C8 C13 170.85(19) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
C7 C8 C9 C10 -178.0(2) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C9 C10 C11 Cl1 -178.44(17) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
Cl1 C11 C12 C13 178.62(18) . . . . ?
C11 C12 C13 C8 -0.1(3) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
C7 C8 C13 C12 178.3(2) . . . . ?
C2 C3 C14 O2 26.3(3) . . . . ?
C4 C3 C14 O2 -147.11(19) . . . . ?
C2 C3 C14 C15 -154.11(17) . . . . ?
C4 C3 C14 C15 32.5(3) . . . . ?
O2 C14 C15 C20 -142.1(2) . . . . ?
C3 C14 C15 C20 38.3(3) . . . . ?
O2 C14 C15 C16 35.6(3) . . . . ?
C3 C14 C15 C16 -144.03(19) . . . . ?
C20 C15 C16 C17 -1.7(3) . . . . ?
C14 C15 C16 C17 -179.41(19) . . . . ?
C15 C16 C17 C18 3.4(3) . . . . ?
C16 C17 C18 C19 -2.0(3) . . . . ?
C16 C17 C18 Cl2 177.80(18) . . . . ?
C17 C18 C19 C20 -1.0(3) . . . . ?
Cl2 C18 C19 C20 179.17(15) . . . . ?
C18 C19 C20 C15 2.7(3) . . . . ?
C16 C15 C20 C19 -1.4(3) . . . . ?
C14 C15 C20 C19 176.28(18) . . . . ?
C4 C5 C21 O3 -142.45(19) . . . . ?
C6 C5 C21 O3 37.9(3) . . . . ?
C4 C5 C21 C22 39.0(3) . . . . ?
C6 C5 C21 C22 -140.60(17) . . . . ?
O3 C21 C22 C23 -153.19(19) . . . . ?
C5 C21 C22 C23 25.3(3) . . . . ?
O3 C21 C22 C27 24.3(3) . . . . ?
C5 C21 C22 C27 -157.22(17) . . . . ?
C27 C22 C23 C24 2.4(3) . . . . ?
C21 C22 C23 C24 179.82(18) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C23 C24 C25 C26 -3.4(3) . . . . ?
C23 C24 C25 Cl3 175.81(16) . . . . ?
C24 C25 C26 C27 2.1(3) . . . . ?
Cl3 C25 C26 C27 -177.05(17) . . . . ?
C25 C26 C27 C22 1.4(3) . . . . ?
C23 C22 C27 C26 -3.6(3) . . . . ?
C21 C22 C27 C26 178.85(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9389132
2 PubChem 11214070
