#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:31:47 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268684 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/29/7242983.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_7242983
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             2021-03-19
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     55.00  88.00   0.50    1.27    --    0.00  38.00-150.00   66
  2  ω     54.00  89.00   0.50    1.27    --    0.00  38.00   0.00   70
  3  ω     -3.00  23.00   0.50    1.27    --    0.00  38.00   0.00   52
  4  ω    -29.00   9.00   0.50    1.27    --    0.00  77.00 -60.00   76
  5  ω     18.00  48.00   0.50    1.27    --    0.00  77.00 -60.00   60
  6  ω     51.00  86.00   0.50    1.27    --    0.00  77.00 -60.00   70
  7  ω    -14.00  19.00   0.50    1.27    --    0.00  38.00-150.00   66
  8  ω     87.00 112.00   0.50    5.07    --   92.40 -82.00  60.00   50
  9  ω     10.00  58.00   0.50    5.07    --   92.40 -82.00  60.00   96
 10  ω      6.00  37.00   0.50    5.07    --   92.40 -30.00 150.00   62
 11  ω     89.00 119.00   0.50    5.07    --   92.40 -82.00-150.00   60
 12  ω      4.00 108.00   0.50    5.07    --   92.40 -61.00 -90.00  208
 13  ω     10.00  52.00   0.50    5.07    --   92.40 -45.00   0.00   84
 14  ω     76.00 112.00   0.50    5.07    --   92.40 -45.00   0.00   72
 15  ω     31.00  65.00   0.50    5.07    --   92.40 -82.00-150.00   68
 16  ω      8.00 114.00   0.50    5.07    --   92.40 -61.00  60.00  212
 17  ω      3.00 107.00   0.50    5.07    --   92.40 -30.00  60.00  208
 18  ω     78.00 176.00   0.50    5.07    --   92.40  15.00-180.00  196
 19  ω     35.00  61.00   0.50    5.07    --   92.40 -45.00-120.00   52
 20  ω     72.00 107.00   0.50    5.07    --   92.40 -45.00-120.00   70
 21  ω     68.00 109.00   0.50    5.07    --   92.40 -82.00 150.00   82
 22  ω     11.00  83.00   0.50    5.07    --   92.40 -61.00-150.00  144
 23  ω     69.00 100.00   0.50    5.07    --   92.40 -30.00 150.00   62
 24  ω     68.00 122.00   0.50    5.07    --   92.40 -82.00 -30.00  108
 25  ω     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       'ω 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/[σ²(Fo²)+(0.1022P)²+0.4341P] where P=(Fo²+2Fc²)/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 > 2σ(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
_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 99.04
_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)
;
_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
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
Cl22 Cl 0.59174(12) -0.12882(7) 0.75033(5) 0.0540(2) Uani 1 1 d . . . . .
Cl15 Cl 0.23208(18) 0.91406(11) 0.02712(6) 0.0885(4) Uani 1 1 d . . . . .
O24 O 0.0890(3) 0.57404(18) 0.39848(11) 0.0455(4) Uani 1 1 d . . . . .
O23 O 0.9076(3) 0.23308(19) 0.36989(12) 0.0483(5) Uani 1 1 d . . . . .
N6 N 0.2480(3) 0.39384(19) 0.47886(13) 0.0370(5) Uani 1 1 d . . . . .
H6 H 0.146862 0.388993 0.517702 0.044 Uiso 1 1 calc R . . . .
N2 N 0.7432(3) 0.4080(2) 0.28550(14) 0.0406(5) Uani 1 1 d . . . . .
C16 C 0.4705(4) 0.2002(2) 0.54355(15) 0.0349(5) Uani 1 1 d . . . . .
C4 C 0.5574(4) 0.3492(2) 0.40740(15) 0.0358(5) Uani 1 1 d . . . . .
C8 C 0.4426(4) 0.4592(2) 0.36266(15) 0.0366(5) Uani 1 1 d . . . . .
C5 C 0.4350(4) 0.3085(2) 0.47838(15) 0.0351(5) Uani 1 1 d . . . . .
C7 C 0.2419(4) 0.4876(2) 0.40998(15) 0.0367(5) Uani 1 1 d . . . . .
C3 C 0.7540(4) 0.3164(2) 0.35833(16) 0.0387(5) Uani 1 1 d . . . . .
C1 C 0.5559(4) 0.4937(2) 0.28760(15) 0.0369(5) Uani 1 1 d . . . . .
C20 C 0.7068(4) 0.0208(2) 0.60826(17) 0.0422(6) Uani 1 1 d . . . . .
H20 H 0.838918 -0.029735 0.609472 0.051 Uiso 1 1 calc R . . . .
C19 C 0.5436(4) -0.0057(2) 0.66905(17) 0.0415(6) Uani 1 1 d . . . . .
C21 C 0.6700(4) 0.1235(2) 0.54574(16) 0.0399(5) Uani 1 1 d . . . . .
H21 H 0.778481 0.142058 0.504715 0.048 Uiso 1 1 calc R . . . .
C9 C 0.4878(4) 0.5958(3) 0.22162(16) 0.0416(6) Uani 1 1 d . . . . .
C17 C 0.3077(4) 0.1687(3) 0.60492(17) 0.0435(6) Uani 1 1 d . . . . .
H17 H 0.173716 0.217208 0.603627 0.052 Uiso 1 1 calc R . . . .
C25 C 0.9282(4) 0.4127(3) 0.22546(17) 0.0444(6) Uani 1 1 d . . . . .
H25A H 1.062342 0.397614 0.256236 0.053 Uiso 1 1 calc R . . . .
H25B H 0.931905 0.504924 0.198187 0.053 Uiso 1 1 calc R . . . .
C18 C 0.3440(4) 0.0662(3) 0.66735(18) 0.0481(6) Uani 1 1 d . . . . .
H18 H 0.235219 0.045674 0.707911 0.058 Uiso 1 1 calc R . . . .
C10 C 0.3355(5) 0.6976(3) 0.24264(17) 0.0480(6) Uani 1 1 d . . . . .
H10 H 0.285444 0.701692 0.298384 0.058 Uiso 1 1 calc R . . . .
C11 C 0.2552(5) 0.7940(3) 0.1827(2) 0.0554(7) Uani 1 1 d . . . . .
H11 H 0.150585 0.860670 0.198254 0.066 Uiso 1 1 calc R . . . .
C26 C 0.9236(5) 0.3079(3) 0.1582(2) 0.0567(7) Uani 1 1 d . . . . .
H26A H 0.783240 0.315280 0.131076 0.068 Uiso 1 1 calc R . . . .
H26B H 0.939588 0.215096 0.184170 0.068 Uiso 1 1 calc R . . . .
C12 C 0.3292(5) 0.7912(3) 0.1013(2) 0.0606(8) Uani 1 1 d . . . . .
C14 C 0.5488(6) 0.5887(4) 0.1360(2) 0.0692(9) Uani 1 1 d . . . . .
H14 H 0.643760 0.517476 0.119127 0.083 Uiso 1 1 calc R . . . .
C27 C 1.1063(6) 0.3309(4) 0.0921(2) 0.0725(10) Uani 1 1 d . . . . .
H27A H 1.108009 0.257912 0.053255 0.109 Uiso 1 1 calc GR . . . .
H27B H 1.244538 0.330650 0.119341 0.109 Uiso 1 1 calc GR . . . .
H27C H 1.081744 0.418577 0.062041 0.109 Uiso 1 1 calc GR . . . .
C13 C 0.4701(6) 0.6859(4) 0.0760(2) 0.0776(11) Uani 1 1 d . . . . .
H13 H 0.511961 0.680116 0.019497 0.093 Uiso 1 1 calc R . . . .
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 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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 N6 H6 123.7 . . ?
C7 N6 H6 123.7 . . ?
C7 N6 C5 112.6(2) . . ?
C3 N2 C25 119.4(2) . . ?
C1 N2 C3 111.5(2) . . ?
C1 N2 C25 128.7(2) . . ?
C21 C16 C5 120.2(2) . . ?
C17 C16 C5 121.1(2) . . ?
C17 C16 C21 118.7(2) . . ?
C8 C4 C3 107.4(2) . . ?
C5 C4 C8 109.1(2) . . ?
C5 C4 C3 143.4(2) . . ?
C4 C8 C7 107.3(2) . . ?
C1 C8 C4 109.6(2) . . ?
C1 C8 C7 143.0(2) . . ?
N6 C5 C16 121.5(2) . . ?
C4 C5 N6 106.5(2) . . ?
C4 C5 C16 132.1(2) . . ?
O24 C7 N6 123.0(2) . . ?
O24 C7 C8 132.4(2) . . ?
N6 C7 C8 104.61(19) . . ?
O23 C3 N2 122.3(2) . . ?
O23 C3 C4 133.0(2) . . ?
N2 C3 C4 104.63(19) . . ?
N2 C1 C9 126.3(2) . . ?
C8 C1 N2 106.8(2) . . ?
C8 C1 C9 126.9(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C21 C20 C19 119.0(2) . . ?
C20 C19 Cl22 119.51(19) . . ?
C18 C19 Cl22 119.1(2) . . ?
C18 C19 C20 121.4(2) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C10 C9 C1 118.2(2) . . ?
C10 C9 C14 117.2(2) . . ?
C14 C9 C1 124.2(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
N2 C25 H25A 108.6 . . ?
N2 C25 H25B 108.6 . . ?
N2 C25 C26 114.6(2) . . ?
H25A C25 H25B 107.6 . . ?
C26 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C19 C18 H18 120.3 . . ?
C17 C18 C19 119.5(3) . . ?
C17 C18 H18 120.3 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C25 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C25 C26 C27 111.3(3) . . ?
H26A C26 H26B 108.0 . . ?
C27 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
C11 C12 Cl15 119.8(2) . . ?
C11 C12 C13 120.4(3) . . ?
C13 C12 Cl15 119.6(3) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
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
Cl22 C19 1.734(2) . ?
Cl15 C12 1.731(3) . ?
O24 C7 1.244(3) . ?
O23 C3 1.228(3) . ?
N6 H6 0.8600 . ?
N6 C5 1.387(3) . ?
N6 C7 1.384(3) . ?
N2 C3 1.421(3) . ?
N2 C1 1.391(3) . ?
N2 C25 1.456(3) . ?
C16 C5 1.448(3) . ?
C16 C21 1.406(3) . ?
C16 C17 1.401(4) . ?
C4 C8 1.424(3) . ?
C4 C5 1.380(3) . ?
C4 C3 1.447(3) . ?
C8 C7 1.445(3) . ?
C8 C1 1.390(3) . ?
C1 C9 1.462(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.387(4) . ?
C20 C21 1.385(3) . ?
C19 C18 1.384(4) . ?
C21 H21 0.9300 . ?
C9 C10 1.378(4) . ?
C9 C14 1.404(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.511(4) . ?
C18 H18 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.385(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.358(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.522(4) . ?
C12 C13 1.379(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.387(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C13 H13 0.9300 . ?
