Chlorinated diketopyrrolopyrrole dye exhibits a three-step polymorphic transition with thermosalient effects
Kikuchi, Yusuke; Matsumoto, Shinya; CrystEngComm 23 (2021) 5882–5890; doi:10.1039/D1CE00454A

data_7242985
_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             2021-03-19
_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                63.183(2)
_cell_angle_beta                 70.379(2)
_cell_angle_gamma                80.704(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0941(2)
_cell_length_b                   10.1582(2)
_cell_length_c                   10.8283(3)
_cell_measurement_reflns_used    5602
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      72.6990
_cell_measurement_theta_min      4.6710
_cell_volume                     933.30(4)
_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 0.995
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     16.00  51.00   0.50    0.73    --    0.00  65.00 124.00   70
  2  \w    111.00 182.00   0.50    2.90    --   92.40  65.00 124.00  142
  3  \w     83.00 112.00   0.50    2.90    --   92.40 -65.00 -10.00   58
  4  \w     44.00  70.00   0.50    2.90    --   92.40 -65.00 -10.00   52
  5  \w    -62.00   1.00   0.50    0.73    --    0.00 -65.00 -10.00  126
  6  \w     29.00  56.00   0.50    0.73    --    0.00  38.00  90.00   54
  7  \w    -11.00  21.00   0.50    0.73    --    0.00 -57.00  90.00   64
  8  \w     40.00  80.00   0.50    0.73    --    0.00  19.00 -30.00   80
  9  \w    -60.00 -20.00   0.50    0.73    --    0.00 -57.00  90.00   80
 10  \w    -17.00  28.00   0.50    0.73    --    0.00  19.00 -30.00   90
 11  \w      3.00  61.00   0.50    2.90    --   92.40 -15.00   0.00  116
 12  \w      3.00  67.00   0.50    2.90    --   92.40 -77.00 -30.00  128
 13  \w      4.00  72.00   0.50    2.90    --   92.40 -30.00-180.00  136
 14  \w     67.00 102.00   0.50    2.90    --   92.40 -61.00  90.00   70
 15  \w     79.00 124.00   0.50    2.90    --   92.40 -82.00-180.00   90
 16  \w      8.00  53.00   0.50    2.90    --   92.40 -82.00 -90.00   90
 17  \w     57.00 124.00   0.50    2.90    --   92.40 -82.00 -90.00  134
 18  \w      9.00 105.00   0.50    2.90    --   92.40 -30.00 -30.00  192
 19  \w     76.00 123.00   0.50    2.90    --   92.40 -82.00  90.00   94
 20  \w     24.00  93.00   0.50    2.90    --   92.40 -45.00-120.00  138
 21  \w     11.00  41.00   0.50    2.90    --   92.40 -82.00-180.00   60
 22  \w      4.00  50.00   0.50    2.90    --   92.40 -61.00 120.00   92
 23  \w     64.00 123.00   0.50    2.90    --   92.40 -82.00   0.00  118
 24  \w      4.00  60.00   0.50    2.90    --   92.40 -61.00  90.00  112
 25  \w     82.00 108.00   0.50    2.90    --   92.40 -15.00   0.00   52
 26  \w     50.00  75.00   0.50    2.90    --   92.40 -82.00  90.00   50
 27  \w     20.00  88.00   0.50    2.90    --   92.40 -61.00-180.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0662174000
_diffrn_orient_matrix_UB_12      0.0913708000
_diffrn_orient_matrix_UB_13      -0.1233709000
_diffrn_orient_matrix_UB_21      -0.1025275000
_diffrn_orient_matrix_UB_22      0.0726154000
_diffrn_orient_matrix_UB_23      0.0939420000
_diffrn_orient_matrix_UB_31      0.1065847000
_diffrn_orient_matrix_UB_32      0.1235311000
_diffrn_orient_matrix_UB_33      -0.0620875000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9702
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.109
_diffrn_reflns_theta_min         4.651
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54421
_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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0420
_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/[\s^2^(Fo^2^)+(0.0761P)^2^+0.1252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3141
_reflns_number_total             3618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00454a3.cif
_cod_data_source_block           exp_582
_cod_depositor_comments
'Adding full bibliography for 7242983--7242986.cif.'
_cod_database_code               7242985
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H16O2N2Cl2
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C17(H17), C10(H10), C14(H14), C21(H21), C20(H20), C18(H18), C11(H11),
 C13(H13)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              87827
_olex2_submission_original_sample_id PRM3O
_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 2.003
_oxdiff_exptl_absorpt_empirical_full_min 0.689