#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/11/7231174.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_7231174
loop_
_publ_author_name
'So, Hee-Soo'
'Minami, Takaya'
'Jindo, Takumi'
'Matsumoto, Shinya'
_publ_section_title
;
 Thermosalient effect of two polymorphs of a diketopyrrolopyrrole dye with
 different crystal systems and molecular arrangements
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              5317
_journal_paper_doi               10.1039/C8CE00940F
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C24 H22 Cl2 N2 O2'
_chemical_formula_sum            'C24 H22 Cl2 N2 O2'
_chemical_formula_weight         441.36
_chemical_melting_point          506
_chemical_name_systematic
3,6-bis(4-chlorophenyl)-2,5-dipropyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-03-07 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.4687(13)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   11.31549(16)
_cell_length_b                   9.66903(15)
_cell_length_c                   9.86401(15)
_cell_measurement_reflns_used    3815
_cell_measurement_temperature    296
_cell_measurement_theta_max      73.77
_cell_measurement_theta_min      4.51
_cell_volume                     1072.35(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5661
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.480
_diffrn_reflns_theta_max         66.480
_diffrn_reflns_theta_min         3.932
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.911
_exptl_absorpt_correction_T_max  0.564
_exptl_absorpt_correction_T_min  0.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460.00
_exptl_crystal_recrystallization_method 'liquid-liquid diffusion method'
_exptl_crystal_size_max          0.649
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.197
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0937P)²+0.1234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1424
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1672
_reflns_number_total             1868
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c8ce00940f2.cif
_cod_data_source_block           xcalibur
_cod_depositor_comments
'Adding full bibliography for 7231174--7231175.cif.'
_cod_database_code               7231174
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-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
Cl1 Cl -0.11591(5) 0.79323(7) 0.38728(7) 0.0810(3) Uani 1 1 d . .
O1 O 0.62151(13) 0.49758(16) 0.78062(13) 0.0581(4) Uani 1 1 d . .
N1 N 0.43453(13) 0.56925(15) 0.68258(13) 0.0432(4) Uani 1 1 d . .
C2 C 0.37133(15) 0.57013(16) 0.55333(16) 0.0395(4) Uani 1 1 d . .
C4 C 0.24995(15) 0.62306(17) 0.52107(16) 0.0396(4) Uani 1 1 d . .
C1 C 0.44423(15) 0.51767(18) 0.46365(17) 0.0427(4) Uani 1 1 d . .
C9 C 0.17252(17) 0.5539(2) 0.42397(18) 0.0473(4) Uani 1 1 d . .
H9 H 0.1973 0.4725 0.3855 0.057 Uiso 1 1 calc R U
C3 C 0.55029(16) 0.51243(18) 0.67912(18) 0.0442(4) Uani 1 1 d . .
C5 C 0.21170(18) 0.7454(2) 0.5761(2) 0.0509(5) Uani 1 1 d . .
H5 H 0.2623 0.7931 0.6407 0.061 Uiso 1 1 calc R U
C10 C 0.38714(19) 0.5921(2) 0.81363(17) 0.0504(5) Uani 1 1 d . .
H10A H 0.3453 0.6798 0.8101 0.061 Uiso 1 1 calc R U
H10B H 0.4530 0.5981 0.8854 0.061 Uiso 1 1 calc R U
C8 C 0.05964(18) 0.6039(2) 0.3838(2) 0.0540(5) Uani 1 1 d . .
H8 H 0.0082 0.5561 0.3202 0.065 Uiso 1 1 calc R U
C7 C 0.02444(18) 0.7261(2) 0.4397(2) 0.0520(5) Uani 1 1 d . .
C6 C 0.0993(2) 0.7968(2) 0.5355(2) 0.0565(5) Uani 1 1 d . .
H6 H 0.0743 0.8786 0.5728 0.068 Uiso 1 1 calc R U
C11 C 0.3036(2) 0.4793(2) 0.8490(2) 0.0618(6) Uani 1 1 d . .
H11A H 0.2793 0.4984 0.9384 0.074 Uiso 1 1 calc R U
H11B H 0.2329 0.4816 0.7836 0.074 Uiso 1 1 calc R U
C12 C 0.3562(3) 0.3366(3) 0.8500(3) 0.0740(7) Uani 1 1 d . .
H12A H 0.2984 0.2705 0.8732 0.089 Uiso 1 1 calc R U
H12B H 0.3786 0.3156 0.7613 0.089 Uiso 1 1 calc R U
H12C H 0.4251 0.3325 0.9162 0.089 Uiso 1 1 calc R U
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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 N1 C3 111.10(13) . .
C2 N1 C10 127.19(15) . .
C3 N1 C10 120.41(14) . .
C1 C2 N1 107.72(15) . .
C1 C2 C4 127.24(15) . .
N1 C2 C4 125.01(15) . .
C5 C4 C9 118.49(17) . .
C5 C4 C2 122.50(16) . .
C9 C4 C2 118.83(16) . .
C2 C1 C1 109.12(18) . 3_666
C2 C1 C3 142.80(16) . 3_666
C1 C1 C3 108.06(19) 3_666 3_666
C8 C9 C4 121.21(17) . .
C8 C9 H9 119.4 . .
C4 C9 H9 119.4 . .
O1 C3 N1 123.33(16) . .
O1 C3 C1 132.70(18) . 3_666
N1 C3 C1 103.96(14) . 3_666
C6 C5 C4 120.65(18) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
N1 C10 C11 113.24(15) . .
N1 C10 H10A 108.9 . .
C11 C10 H10A 108.9 . .
N1 C10 H10B 108.9 . .
C11 C10 H10B 108.9 . .
H10A C10 H10B 107.7 . .
C7 C8 C9 118.95(18) . .
C7 C8 H8 120.5 . .
C9 C8 H8 120.5 . .
C6 C7 C8 121.05(19) . .
C6 C7 Cl1 119.25(16) . .
C8 C7 Cl1 119.70(16) . .
C7 C6 C5 119.64(18) . .
C7 C6 H6 120.2 . .
C5 C6 H6 120.2 . .
C12 C11 C10 114.0(2) . .
C12 C11 H11A 108.7 . .
C10 C11 H11A 108.7 . .
C12 C11 H11B 108.7 . .
C10 C11 H11B 108.7 . .
H11A C11 H11B 107.6 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C7 1.740(2) .
O1 C3 1.221(2) .
N1 C2 1.390(2) .
N1 C3 1.424(2) .
N1 C10 1.471(2) .
C2 C1 1.373(2) .
C2 C4 1.467(2) .
C4 C5 1.390(3) .
C4 C9 1.394(3) .
C1 C1 1.421(3) 3_666
C1 C3 1.446(3) 3_666
C9 C8 1.381(3) .
C9 H9 0.9300 .
C3 C1 1.446(3) 3_666
C5 C6 1.382(3) .
C5 H5 0.9300 .
C10 C11 1.509(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C8 C7 1.381(3) .
C8 H8 0.9300 .
C7 C6 1.377(3) .
C6 H6 0.9300 .
C11 C12 1.503(3) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
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_4
C3 N1 C2 C1 -1.33(19) .
C10 N1 C2 C1 -168.19(17) .
C3 N1 C2 C4 -179.32(16) .
C10 N1 C2 C4 13.8(3) .
C1 C2 C4 C5 -135.22(19) .
N1 C2 C4 C5 42.4(3) .
C1 C2 C4 C9 39.9(3) .
N1 C2 C4 C9 -142.50(18) .
N1 C2 C1 C1 0.1(2) 3_666
C4 C2 C1 C1 178.05(18) 3_666
N1 C2 C1 C3 -178.2(2) 3_666
C4 C2 C1 C3 -0.2(4) 3_666
C5 C4 C9 C8 -0.8(3) .
C2 C4 C9 C8 -176.10(17) .
C2 N1 C3 O1 -178.16(18) .
C10 N1 C3 O1 -10.3(3) .
C2 N1 C3 C1 1.93(19) 3_666
C10 N1 C3 C1 169.81(15) 3_666
C9 C4 C5 C6 0.2(3) .
C2 C4 C5 C6 175.34(18) .
C2 N1 C10 C11 66.4(2) .
C3 N1 C10 C11 -99.3(2) .
C4 C9 C8 C7 1.2(3) .
C9 C8 C7 C6 -1.0(3) .
C9 C8 C7 Cl1 178.33(15) .
C8 C7 C6 C5 0.4(3) .
Cl1 C7 C6 C5 -178.89(16) .
C4 C5 C6 C7 0.0(3) .
N1 C10 C11 C12 55.4(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064701
