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_7242983
_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                87.008(4)
_cell_angle_beta                 88.263(3)
_cell_angle_gamma                88.159(3)
_cell_formula_units_Z            2
_cell_length_a                   6.1089(2)
_cell_length_b                   9.6567(5)
_cell_length_c                   15.8773(6)
_cell_measurement_reflns_used    4345
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      72.3800
_cell_measurement_theta_min      4.5950
_cell_volume                     934.49(7)
_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 0.989
_diffrn_measured_fraction_theta_max 0.938
_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     55.00  88.00   0.50    1.27    --    0.00  38.00-150.00   66
  2  \w     54.00  89.00   0.50    1.27    --    0.00  38.00   0.00   70
  3  \w     -3.00  23.00   0.50    1.27    --    0.00  38.00   0.00   52
  4  \w    -29.00   9.00   0.50    1.27    --    0.00  77.00 -60.00   76
  5  \w     18.00  48.00   0.50    1.27    --    0.00  77.00 -60.00   60
  6  \w     51.00  86.00   0.50    1.27    --    0.00  77.00 -60.00   70
  7  \w    -14.00  19.00   0.50    1.27    --    0.00  38.00-150.00   66
  8  \w     87.00 112.00   0.50    5.07    --   92.40 -82.00  60.00   50
  9  \w     10.00  58.00   0.50    5.07    --   92.40 -82.00  60.00   96
 10  \w      6.00  37.00   0.50    5.07    --   92.40 -30.00 150.00   62
 11  \w     89.00 119.00   0.50    5.07    --   92.40 -82.00-150.00   60
 12  \w      4.00 108.00   0.50    5.07    --   92.40 -61.00 -90.00  208
 13  \w     10.00  52.00   0.50    5.07    --   92.40 -45.00   0.00   84
 14  \w     76.00 112.00   0.50    5.07    --   92.40 -45.00   0.00   72
 15  \w     31.00  65.00   0.50    5.07    --   92.40 -82.00-150.00   68
 16  \w      8.00 114.00   0.50    5.07    --   92.40 -61.00  60.00  212
 17  \w      3.00 107.00   0.50    5.07    --   92.40 -30.00  60.00  208
 18  \w     78.00 176.00   0.50    5.07    --   92.40  15.00-180.00  196
 19  \w     35.00  61.00   0.50    5.07    --   92.40 -45.00-120.00   52
 20  \w     72.00 107.00   0.50    5.07    --   92.40 -45.00-120.00   70
 21  \w     68.00 109.00   0.50    5.07    --   92.40 -82.00 150.00   82
 22  \w     11.00  83.00   0.50    5.07    --   92.40 -61.00-150.00  144
 23  \w     69.00 100.00   0.50    5.07    --   92.40 -30.00 150.00   62
 24  \w     68.00 122.00   0.50    5.07    --   92.40 -82.00 -30.00  108
 25  \w     16.00  42.00   0.50    5.07    --   92.40 -82.00 -30.00   52
;
_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      -0.0192014000
_diffrn_orient_matrix_UB_12      -0.1427086000
_diffrn_orient_matrix_UB_13      -0.0377638000
_diffrn_orient_matrix_UB_21      -0.0122035000
_diffrn_orient_matrix_UB_22      0.0708902000
_diffrn_orient_matrix_UB_23      -0.0890055000
_diffrn_orient_matrix_UB_31      0.2513891000
_diffrn_orient_matrix_UB_32      -0.0123703000
_diffrn_orient_matrix_UB_33      -0.0100048000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8759
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.689
_diffrn_reflns_theta_min         4.587
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68008
_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 light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0555
_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^)+(0.1022P)^2^+0.4341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2887
_reflns_number_total             3600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00454a3.cif
_cod_data_source_block           prm3_red
_cod_depositor_comments
'Adding full bibliography for 7242983--7242986.cif.'
_cod_database_code               7242983
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H16O2N2Cl2
_reflns_odcompleteness_completeness 99.04
_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), C20(H20), C21(H21), C17(H17), C18(H18), C10(H10), C11(H11), C14(H14),
 C13(H13)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              56048
_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 2.264
_oxdiff_exptl_absorpt_empirical_full_min 0.481