#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:31:47 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268684 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/29/7242984.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_7242984
loop_
_publ_author_name
'Kikuchi, Yusuke'
'Matsumoto, Shinya'
_publ_section_title
;
 Chlorinated diketopyrrolopyrrole dye exhibits a three-step polymorphic
 transition with thermosalient effects
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              5882
_journal_page_last               5890
_journal_paper_doi               10.1039/D1CE00454A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C21 H16 Cl2 N2 O2'
_chemical_formula_sum            'C21 H16 Cl2 N2 O2'
_chemical_formula_weight         399.26
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-26 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                103.927(8)
_cell_angle_beta                 96.226(8)
_cell_angle_gamma                104.186(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5775(9)
_cell_length_b                   7.9456(8)
_cell_length_c                   16.2096(13)
_cell_measurement_reflns_used    2173
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      29.3770
_cell_measurement_theta_min      3.1650
_cell_volume                     903.71(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -15.00   0.50   27.09    --   -0.10 -82.00  60.00  148
  2  ω    -16.00  29.00   0.50   27.09    --   -0.10  77.00  60.00   90
  3  ω     49.00  77.00   0.50   27.09    --   -0.10  77.00  60.00   56
  4  ω    -84.00 -30.00   0.50   27.09    --   -0.10 -77.00-150.00  108
  5  ω    -45.00  27.00   0.50   27.09    --   -0.10 -77.00 -90.00  144
  6  ω    -67.00  81.00   0.50   27.09    --   -0.10   0.00 -90.00  296
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0651429000
_diffrn_orient_matrix_UB_12      -0.0590265000
_diffrn_orient_matrix_UB_13      0.0159541000
_diffrn_orient_matrix_UB_21      -0.0125669000
_diffrn_orient_matrix_UB_22      -0.0698038000
_diffrn_orient_matrix_UB_23      -0.0386507000
_diffrn_orient_matrix_UB_31      0.0722855000
_diffrn_orient_matrix_UB_32      -0.0287712000
_diffrn_orient_matrix_UB_33      0.0187234000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14758
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.271
_diffrn_reflns_theta_min         3.238
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.756
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0547
_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)+(0.0727P)²+0.2850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1571
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2746
_reflns_number_total             4700
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00454a3.cif
_cod_data_source_block           prm3v3rd
_cod_depositor_comments
'Adding full bibliography for 7242983--7242986.cif.'
_cod_database_code               7242984
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H16O2N2Cl2
_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.
;
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00a,H00b), C00L(H00c,H00d)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00H(H00H), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q)
2.c Idealised Me refined as rotating group:
 C00R(H00e,H00f,H00g)
;
_olex2_submission_original_sample_id PRM3V
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.430
_oxdiff_exptl_absorpt_empirical_full_min 0.573
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
Cl01 Cl -0.21168(10) 0.08628(11) 0.21592(5) 0.0484(2) Uani 1 1 d . . . . .
Cl02 Cl 0.99730(12) 1.32143(11) 1.04568(5) 0.0542(2) Uani 1 1 d . . . . .
O003 O 0.6144(3) 1.0426(3) 0.61501(12) 0.0417(5) Uani 1 1 d . . . . .
O004 O 0.2945(3) 0.2963(3) 0.63246(13) 0.0418(5) Uani 1 1 d . . . . .
N005 N 0.4821(3) 0.5611(3) 0.73050(13) 0.0317(5) Uani 1 1 d . . . . .
N006 N 0.4079(3) 0.7849(3) 0.52106(13) 0.0344(5) Uani 1 1 d . . . . .
H006 H 0.389904 0.828975 0.478383 0.041 Uiso 1 1 calc R . . . .
C007 C 0.3894(4) 0.5866(3) 0.59817(15) 0.0296(5) Uani 1 1 d . . . . .
C008 C 0.5627(3) 0.7380(3) 0.73129(15) 0.0284(5) Uani 1 1 d . . . . .
C009 C 0.1942(4) 0.4816(4) 0.44436(16) 0.0312(6) Uani 1 1 d . . . . .
C00A C 0.5238(4) 0.8849(4) 0.59977(16) 0.0314(6) Uani 1 1 d . . . . .
C00B C 0.3736(4) 0.4566(4) 0.64830(16) 0.0313(6) Uani 1 1 d . . . . .
C00C C 0.5093(3) 0.7546(3) 0.65027(15) 0.0288(5) Uani 1 1 d . . . . .
C00D C 0.8689(4) 1.1534(4) 0.95412(17) 0.0354(6) Uani 1 1 d . . . . .
C00E C 0.6695(4) 0.8801(3) 0.80875(15) 0.0296(5) Uani 1 1 d . . . . .
C00F C 0.3251(4) 0.6073(3) 0.51893(16) 0.0301(5) Uani 1 1 d . . . . .
C00G C -0.0559(4) 0.2389(4) 0.30430(17) 0.0352(6) Uani 1 1 d . . . . .
C00H C 0.1153(4) 0.3040(4) 0.44567(17) 0.0353(6) Uani 1 1 d . . . . .
H00H H 0.148389 0.267705 0.494129 0.042 Uiso 1 1 calc R . . . .
C00I C 0.3919(4) 0.4058(4) 0.84323(17) 0.0359(6) Uani 1 1 d . . . . .
H00A H 0.282125 0.321234 0.805015 0.043 Uiso 1 1 calc R . . . .
H00B H 0.357713 0.510514 0.873964 0.043 Uiso 1 1 calc R . . . .
C00J C 0.7993(4) 1.0288(4) 0.80061(17) 0.0336(6) Uani 1 1 d . . . . .
H00J H 0.819335 1.036807 0.745907 0.040 Uiso 1 1 calc R . . . .
C00K C 0.0197(4) 0.4119(4) 0.30107(17) 0.0386(6) Uani 1 1 d . . . . .
H00K H -0.012934 0.447071 0.252189 0.046 Uiso 1 1 calc R . . . .
C00L C 0.5379(4) 0.4633(4) 0.79064(16) 0.0340(6) Uani 1 1 d . . . . .
H00C H 0.650141 0.539932 0.829838 0.041 Uiso 1 1 calc R . . . .
H00D H 0.565948 0.356634 0.757906 0.041 Uiso 1 1 calc R . . . .
C00M C -0.0109(4) 0.1813(4) 0.37644(18) 0.0386(6) Uani 1 1 d . . . . .
H00M H -0.064194 0.063738 0.377939 0.046 Uiso 1 1 calc R . . . .
C00N C 0.7368(4) 1.0118(4) 0.96379(17) 0.0391(7) Uani 1 1 d . . . . .
H00N H 0.714321 1.007255 1.018603 0.047 Uiso 1 1 calc R . . . .
C00O C 0.9003(4) 1.1666(4) 0.87296(19) 0.0382(6) Uani 1 1 d . . . . .
H00O H 0.987492 1.265914 0.866937 0.046 Uiso 1 1 calc R . . . .
C00P C 0.1450(4) 0.5340(4) 0.37109(17) 0.0358(6) Uani 1 1 d . . . . .
H00P H 0.196683 0.651692 0.369217 0.043 Uiso 1 1 calc R . . . .
C00Q C 0.6360(4) 0.8743(4) 0.89164(16) 0.0345(6) Uani 1 1 d . . . . .
H00Q H 0.545771 0.777896 0.898253 0.041 Uiso 1 1 calc R . . . .
C00R C 0.4668(5) 0.3170(4) 0.90777(19) 0.0444(7) Uani 1 1 d . . . . .
H00E H 0.497801 0.211904 0.877091 0.067 Uiso 1 1 calc GR . . . .
H00F H 0.374243 0.282244 0.941226 0.067 Uiso 1 1 calc GR . . . .
H00G H 0.575288 0.401074 0.945506 0.067 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
C008 N005 C00B 111.9(2) . . ?
C008 N005 C00L 127.6(2) . . ?
C00B N005 C00L 117.7(2) . . ?
C00F N006 C00A 113.1(2) . . ?
C00C C007 C00B 108.5(2) . . ?
C00F C007 C00B 142.7(2) . . ?
C00F C007 C00C 108.8(2) . . ?
N005 C008 C00E 124.0(2) . . ?
C00C C008 N005 107.5(2) . . ?
C00C C008 C00E 128.3(2) . . ?
C00H C009 C00F 119.7(2) . . ?
C00P C009 C00F 121.5(2) . . ?
C00P C009 C00H 118.9(2) . . ?
O003 C00A N006 124.1(2) . . ?
O003 C00A C00C 132.6(2) . . ?
N006 C00A C00C 103.3(2) . . ?
O004 C00B N005 122.9(2) . . ?
O004 C00B C007 133.9(2) . . ?
N005 C00B C007 103.2(2) . . ?
C007 C00C C00A 108.2(2) . . ?
C008 C00C C007 108.9(2) . . ?
C008 C00C C00A 142.8(2) . . ?
C00N C00D Cl02 119.0(2) . . ?
C00N C00D C00O 121.1(2) . . ?
C00O C00D Cl02 119.8(2) . . ?
C00J C00E C008 120.0(2) . . ?
C00J C00E C00Q 118.5(2) . . ?
C00Q C00E C008 121.4(2) . . ?
N006 C00F C009 122.1(2) . . ?
C007 C00F N006 106.6(2) . . ?
C007 C00F C009 131.3(2) . . ?
C00K C00G Cl01 119.2(2) . . ?
C00K C00G C00M 121.9(2) . . ?
C00M C00G Cl01 118.9(2) . . ?
C00M C00H C009 121.3(3) . . ?
C00L C00I C00R 109.9(2) . . ?
C00E C00J C00O 121.0(2) . . ?
C00G C00K C00P 119.5(3) . . ?
N005 C00L C00I 113.7(2) . . ?
C00H C00M C00G 118.1(3) . . ?
C00D C00N C00Q 119.8(3) . . ?
C00D C00O C00J 119.0(3) . . ?
C00K C00P C009 120.3(3) . . ?
C00N C00Q C00E 120.4(3) . . ?
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
Cl01 C00G 1.735(3) . ?
Cl02 C00D 1.740(3) . ?
O003 C00A 1.223(3) . ?
O004 C00B 1.217(3) . ?
N005 C008 1.384(3) . ?
N005 C00B 1.427(3) . ?
N005 C00L 1.473(3) . ?
N006 C00A 1.399(3) . ?
N006 C00F 1.387(3) . ?
C007 C00B 1.451(4) . ?
C007 C00C 1.420(3) . ?
C007 C00F 1.385(3) . ?
C008 C00C 1.379(3) . ?
C008 C00E 1.468(3) . ?
C009 C00F 1.455(3) . ?
C009 C00H 1.397(4) . ?
C009 C00P 1.393(4) . ?
C00A C00C 1.458(4) . ?
C00D C00N 1.364(4) . ?
C00D C00O 1.386(4) . ?
C00E C00J 1.383(4) . ?
C00E C00Q 1.403(3) . ?
C00G C00K 1.370(4) . ?
C00G C00M 1.393(4) . ?
C00H C00M 1.381(4) . ?
C00I C00L 1.518(4) . ?
C00I C00R 1.529(4) . ?
C00J C00O 1.391(4) . ?
C00K C00P 1.384(4) . ?
C00N C00Q 1.388(4) . ?
