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_7226997
_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_absolute_configuration ad
_chemical_formula_moiety         'C24 H28 N2 O2 S2'
_chemical_formula_sum            'C24 H28 N2 O2 S2'
_chemical_formula_weight         440.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 106.106(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0248(4)
_cell_length_b                   5.61472(12)
_cell_length_c                   25.7171(6)
_cell_measurement_reflns_used    11298
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.5380
_cell_measurement_theta_min      3.7960
_cell_volume                     2223.07(10)
_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 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega -108.00  -12.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000  150.0000 96

  2 omega  -70.00   21.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   77.0000  -60.0000 91

  3 omega  -11.00   16.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -60.0000 27

  4 omega   31.00   83.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000 -120.0000 52

  5 omega   46.00   94.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000  -60.0000 48

  6 omega   37.00   76.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000    0.0000 39

  7 omega  111.00  171.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   30.0000   30.0000 60

  8 omega   74.00  134.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -30.0000 60

  9 omega   68.00  104.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000 -120.0000 36

 10 omega   33.00  116.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000 -150.0000 83

 11 omega   35.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000 -180.0000 56

 12 omega  -30.00   65.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       42.3292  -38.0000    0.0000 95

 13 omega   11.00  116.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       42.3292   77.0000   30.0000 105

 14 omega   16.00  112.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       42.3292   57.0000  -60.0000 96

 15 omega   80.00  176.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   90.0000 96

 16 omega   77.00  175.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  150.0000 98

 17 omega   23.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000   60.0000 86

 18 omega   77.00  175.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000 -150.0000 98

 19 omega   33.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  150.0000 65

 20 omega   77.00  175.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -90.0000 98

 21 omega  -50.00   34.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000 -150.0000 84

 22 omega   11.00  116.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       42.3292   77.0000 -150.0000 105

 23 omega   11.00  116.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       42.3292   77.0000  120.0000 105

 24 omega   73.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   30.0000 25
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      -0.0341691000
_diffrn_orient_matrix_UB_12      0.0270488000
_diffrn_orient_matrix_UB_13      -0.0619525000
_diffrn_orient_matrix_UB_21      -0.0139656000
_diffrn_orient_matrix_UB_22      0.2683086000
_diffrn_orient_matrix_UB_23      0.0068360000
_diffrn_orient_matrix_UB_31      0.0929758000
_diffrn_orient_matrix_UB_32      0.0501449000
_diffrn_orient_matrix_UB_33      -0.0030635000
_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  0.0338
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            24225
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.711
_diffrn_reflns_theta_min         3.781
_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    2.352
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.530
_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    1.316
_exptl_crystal_description       needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.6707
_exptl_crystal_size_mid          0.0541
_exptl_crystal_size_min          0.0131
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 3170 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8553
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0509P)^2^+0.4263P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                7909
_reflns_number_total             8553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce02157c2.cif
_cod_data_source_block           1E
_cod_depositor_comments
'Adding full bibliography for 7226989--7226997.cif.'
_cod_database_code               7226997
_nottingham_internal_coll_name   OFFPLP
_nottingham_internal_coll_number 14790
_nottingham_internal_coll_client FFP/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '7.5000, 30.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   16/06/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 22/06/2015
_nottingham_internal_process_user pczfp
_nottingham_internal_solution_date 22/06/2015
_nottingham_internal_solution_user pczfp
_nottingham_internal_refinement_date 22/06/2016
_nottingham_internal_refinement_user pczfp
_nottingham_internal_self_validation_date 17/08/2016
_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         'C24 H28 N2 O2 S2'
_chemical_oxdiff_usercomment
'OFFPLP #14790 GVB-601 IN FOMBLIN FILM ON A MICROMOUNT FOR FFP/DBA'
_reflns_odcompleteness_completeness 99.86
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16A(H16A), C21A(H21A), C16B(H16B), C21B(H21B)
2.b Secondary CH2 refined with riding coordinates:
 C15A(H15A,H15B), C18A(H18A,H18B), C20A(H20A,H20B), C23A(H23A,H23B), C15B(H15C,
 H15D), C18B(H18C,H18D), C20B(H20C,H20D), C23B(H23C,H23D)
2.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C12A(H12A), C13A(H13A), C14A(H14A), C1B(H1B),
 C2B(H2B), C3B(H3B), C12B(H12B), C13B(H13B), C14B(H14B)
2.d Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C19A(H19A,H19B,H19C), C22A(H22A,H22B,H22C), C24A(H24A,
 H24B,H24C), C17B(H17D,H17E,H17F), C19B(H19D,H19E,H19F), C22B(H22D,H22E,H22F),
 C24B(H24D,H24E,H24F)
;
_shelx_res_checksum              96770
_olex2_date_sample_data_collection 2015-06-16
_olex2_date_sample_submission    2015-05-19
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'