Effects of diphenyl-vinyl-substituted diketopyrrolopyrrole isomers on stacking and luminescence.
Wang, Ruixin; Yang, Puxi; Chen, Huizhi; Lan, Songming; Li, Haoyu; Fan, Wei; Gao, Guangpeng; Li, Xiaofang; RSC advances 15 (2025) 23681–23686; doi:10.1039/d5ra03935e

data_7250770
_publ_section_title
;
 Effects of diphenyl-vinyl-substituted diketopyrrolopyrrole isomers on
 stacking and luminescence.
;
_journal_issue                   29
_journal_name_full               'RSC advances'
_journal_page_first              23681
_journal_page_last               23686
_journal_paper_doi               10.1039/d5ra03935e
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C H Cl3, C50 H56 N2 O2'
_chemical_formula_sum            'C51 H57 Cl3 N2 O2'
_chemical_formula_weight         836.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-15 deposited with the CCDC.	2025-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.653(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.8626(8)
_cell_length_b                   9.8820(2)
_cell_length_c                   31.4686(7)
_cell_measurement_reflns_used    18734
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.5230
_cell_measurement_theta_min      2.9160
_cell_volume                     8849.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.946
_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   -114.00 -39.00   0.50   10.00    --  -47.28 -48.00  83.00  150
  2  \w    -38.00 -12.00   0.50   10.00    --  -47.28  48.00-128.00   52
  3  \w     53.00  78.00   0.50   10.00    --   47.28  48.00-128.00   50
  4  \w    -23.00  40.00   0.50   10.00    --   47.28 -48.00  83.00  126
  5  \w   -174.00-148.00   0.50   40.00    -- -104.00 -48.00  83.00   52
  6  \w     93.00 174.00   0.50   40.00    --  104.75  48.00-128.00  162
  7  \w    -66.00  24.00   0.50   10.00    --  -47.28  77.00-120.00  180
  8  \w    -21.00  15.00   0.50   10.00    --  -47.28  19.00  30.00   72
  9  \w    -63.00 -36.00   0.50   40.00    -- -104.00  57.00 150.00   54
 10  \w    -62.00 -36.00   0.50   40.00    -- -104.00  57.00  60.00   52
 11  \w   -171.00-145.00   0.50   40.00    -- -104.00 -38.00 -30.00   52
 12  \w    -98.00 -39.00   0.50   40.00    -- -104.00  77.00 -90.00  118
 13  \w   -131.00-106.00   0.50   40.00    -- -104.00 -38.00 -30.00   50
 14  \w    -64.00 -39.00   0.50   40.00    -- -104.00  57.00-120.00   50
 15  \w    -64.00 -36.00   0.50   40.00    -- -104.00  57.00  90.00   56
 16  \w   -170.00-127.00   0.50   40.00    -- -104.00 -57.00-180.00   86
 17  \w   -122.00 -96.00   0.50   40.00    -- -104.00 -57.00-180.00   52
 18  \w   -107.00 -60.00   0.50   40.00    -- -104.00 125.00 -30.00   94
 19  \w    -59.00 -33.00   0.50   40.00    -- -104.00  57.00 120.00   52
 20  \w     34.00  68.00   0.50   40.00    --  104.75 -57.00 -60.00   68
 21  \w     37.00 107.00   0.50   40.00    --  104.75 -77.00  30.00  140
 22  \w     33.00  68.00   0.50   40.00    --  104.75 -57.00  90.00   70
 23  \w     93.00 172.00   0.50   40.00    --  104.75  57.00 150.00  158
 24  \w     36.00  63.00   0.50   40.00    --  104.75 -57.00 120.00   54
 25  \w     38.00  64.00   0.50   40.00    --  104.75 -57.00 -90.00   52
 26  \w     37.00  66.00   0.50   40.00    --  104.75 -57.00 150.00   58
 27  \w     36.00  64.00   0.50   40.00    --  104.75 -57.00 -30.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0373232000
_diffrn_orient_matrix_UB_12      0.0846666000
_diffrn_orient_matrix_UB_13      0.0341583000
_diffrn_orient_matrix_UB_21      0.0361718000
_diffrn_orient_matrix_UB_22      -0.0352013000
_diffrn_orient_matrix_UB_23      -0.0243018000
_diffrn_orient_matrix_UB_31      -0.0151314000
_diffrn_orient_matrix_UB_32      0.1260274000
_diffrn_orient_matrix_UB_33      -0.0297566000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            62171
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.022
_diffrn_reflns_theta_min         2.443
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             3552
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.782
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1053
_refine_ls_number_reflns         17716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.782
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.1069
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2811
_refine_ls_wR_factor_ref         0.2960
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11073
_reflns_number_total             17716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra03935e2.cif
_cod_data_source_block           c26-4dp-dpp_auto
_cod_database_code               7250770
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'C H N O'
_shelx_estimated_absorpt_t_max   0.734
_shelx_estimated_absorpt_t_min   0.514
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C110(H110), C83(H83), C56(H56), C48(H48), C2(H2), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C109(H10A,H10B), C47(H47A,H47B), C55(H55A,H55B), C82(H82A,H82B), C88(H88A,
 H88B), C115(H11A,H11B), C58(H58A,H58B), C61(H61A,H61B), C53(H53A,H53B),
 C57(H57A,H57B), C111(H11C,H11D), C49(H49A,H49B), C112(H11E,H11F), C84(H84A,
 H84B), C85(H85A,H85B), C50(H50A,H50B), C59(H59A,H59B), C113(H11J,H11K),
 C86(H86A,H86B), C51(H51A,H51B)
2.c Aromatic/amide H refined with riding coordinates:
 C102(H102), C75(H75), C74(H74), C91(H91), C95(H95), C103(H103), C76(H76),
 C92(H92), C44(H44), C34(H34), C97(H97), C64(H64), C65(H65), C20(H20), C32(H32),
  C94(H94), C68(H68), C18(H18), C24(H24), C23(H23), C17(H17), C35(H35),
 C101(H101), C26(H26), C21(H21), C38(H38), C100(H100), C73(H73), C67(H67),
 C37(H37), C98(H98), C31(H31), C99(H99), C29(H29), C43(H43), C72(H72), C30(H30),
  C27(H27), C28(H28), C42(H42), C40(H40), C70(H70), C71(H71), C41(H41)
2.d Idealised Me refined as rotating group:
 C62(H62A,H62B,H62C), C116(H11G,H11H,H11I), C54(H54A,H54B,H54C), C89(H89A,H89B,
 H89C), C114(H11L,H11M,H11N), C60(H60A,H60B,H60C), C52(H52A,H52B,H52C),
 C87(H87A,H87B,H87C)
;
_shelx_res_checksum              83197
_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 3.256
_oxdiff_exptl_absorpt_empirical_full_min 0.488