Solid state supramolecular structure of diketopyrrolopyrrole chromophores: correlating stacking geometry with visible light absorption
Pop, Flavia; Lewis, William; Amabilino, David B.; CrystEngComm 18 (2016) 8933–; doi:10.1039/C6CE02157C

data_7226996
_publ_section_title
;
 Solid state supramolecular structure of diketopyrrolopyrrole
 chromophores: correlating stacking geometry with visible light absorption
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              8933
_journal_paper_doi               10.1039/C6CE02157C
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C26 H30 Br2 N2 O2 S2'
_chemical_formula_sum            'C26 H30 Br2 N2 O2 S2'
_chemical_formula_weight         626.46
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-05 deposited with the CCDC.
2016-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.6632(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.8550(2)
_cell_length_b                   5.37336(5)
_cell_length_c                   16.5750(2)
_cell_measurement_reflns_used    15244
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0350
_cell_measurement_theta_min      3.2640
_cell_volume                     1303.07(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3271
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -25.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573  -77.0000 -120.0000 98

  2 omega   18.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   77.0000    0.0000 91

  3 omega  101.00  149.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   90.0000 48

  4 omega   68.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000  -90.0000 48

  5 omega  106.00  132.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  150.0000 26

  6 omega   65.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   15.0000   30.0000 112

  7 omega  110.00  135.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000  -60.0000 25

  8 omega   28.00   53.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000    0.0000 25

  9 omega   83.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  122.0000    8.0000 92

 10 omega   73.00  120.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000  -30.0000 47

 11 omega   67.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000  -60.0000 26

 12 omega   46.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000  -60.0000 57

 13 omega   34.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   30.0000 50

 14 omega   46.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  -90.0000 52

 15 omega   40.00   96.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  -30.0000 56

 16 omega   68.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000    0.0000 36

 17 omega  108.00  138.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  -60.0000 30

 18 omega   42.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000 -150.0000 48

 19 omega   90.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -110.0000   17.7237 25

 20 omega   13.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   77.0000  120.0000 101

 21 omega   18.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   57.0000 -120.0000 93

 22 omega  -26.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573  -57.0000   90.0000 94

 23 omega   82.00  174.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  150.0000 92

 24 omega   74.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000    0.0000 102

 25 omega   75.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   74.0000   43.5701 100

 26 omega   84.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   30.0000 -120.0000 94

 27 omega   33.00  135.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000   90.0000 102

 28 omega   74.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   90.0000 102

 29 omega   78.00  173.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000 -180.0000 95

 30 omega   78.00  173.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -90.0000 95

 31 omega   74.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   79.0000  -44.7303 103

 32 omega   78.00  173.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000 -120.0000 95

 33 omega   78.00  173.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -60.0000 95

 34 omega   35.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000   90.0000 63

 35 omega  -49.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000   60.0000 82

 36 omega   13.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   77.0000   60.0000 101

 37 omega   13.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   77.0000  -90.0000 101

 38 omega   78.00  173.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  150.0000 95

 39 omega   35.00  121.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000  120.0000 86

 40 omega   78.00  173.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000 -150.0000 95

 41 omega   78.00  173.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000    0.0000 95

 42 omega   74.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   60.0000 102

 43 omega   33.00  135.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000  -90.0000 102
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      -0.0220970000
_diffrn_orient_matrix_UB_12      -0.2421115000
_diffrn_orient_matrix_UB_13      0.0376959000
_diffrn_orient_matrix_UB_21      -0.0161517000
_diffrn_orient_matrix_UB_22      0.1510319000
_diffrn_orient_matrix_UB_23      0.0717612000
_diffrn_orient_matrix_UB_31      -0.1016462000
_diffrn_orient_matrix_UB_32      0.0285480000
_diffrn_orient_matrix_UB_33      -0.0597788000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28052
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.309
_diffrn_reflns_theta_min         3.278
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    5.656
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.377
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       needle
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.3253
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.0177
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0248
_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^)+(0.0390P)^2^+0.8179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0699
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2548
_reflns_number_total             2646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce02157c2.cif
_cod_data_source_block           1D
_cod_depositor_comments
'Adding full bibliography for 7226989--7226997.cif.'
_cod_database_code               7226996
_nottingham_internal_coll_name   OFFPLB
_nottingham_internal_coll_number 14289
_nottingham_internal_coll_client FFP/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '5.0000, 20.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczfp
_nottingham_internal_coll_date   08/01/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 09/01/2015
_nottingham_internal_process_user pczfp
_nottingham_internal_solution_date 09/01/2015
_nottingham_internal_solution_user pczfp
_nottingham_internal_refinement_date 09/01/2015
_nottingham_internal_refinement_user pczfp
_nottingham_internal_self_validation_date 16/082016
_nottingham_internal_self_validation_user pczfp/pczwl
_nottingham_internal_validation_date 4/10/2016
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 4/10/2016
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C26 H30 Br2 N2 O2 S2'
_reflns_odcompleteness_completeness 100.00
_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
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
;
_shelx_res_checksum              56793
_olex2_date_sample_data_collection 2015-01-15
_olex2_date_sample_submission    2014-12-16
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'