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_7242984
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -89.00 -15.00   0.50   27.09    --   -0.10 -82.00  60.00  148
  2  \w    -16.00  29.00   0.50   27.09    --   -0.10  77.00  60.00   90
  3  \w     49.00  77.00   0.50   27.09    --   -0.10  77.00  60.00   56
  4  \w    -84.00 -30.00   0.50   27.09    --   -0.10 -77.00-150.00  108
  5  \w    -45.00  27.00   0.50   27.09    --   -0.10 -77.00 -90.00  144
  6  \w    -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       '\w 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/[\s^2^(Fo^2^)+(0.0727P)^2^+0.2850P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_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)
;
_shelx_res_checksum              44489
_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