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_7226991
_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         'C18 H14 N2 O4 S2'
_chemical_formula_sum            'C18 H14 N2 O4 S2'
_chemical_formula_weight         386.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_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                 97.914(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7666(8)
_cell_length_b                   4.7286(3)
_cell_length_c                   25.9341(13)
_cell_measurement_reflns_used    3082
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.1220
_cell_measurement_theta_min      3.2200
_cell_volume                     1672.15(17)
_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 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega   22.00  113.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5073   37.0000  120.0000 91

  2 omega   63.00   90.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5073 -125.0000 -150.0000 27

  3 omega   24.00  108.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5073   37.0000 -150.0000 84

  4 omega   91.00  173.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000 -120.0000 82

  5 omega  102.00  144.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -15.0000 -120.0000 42

  6 omega   33.00   87.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   90.0000 54

  7 omega   29.00   58.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -15.0000 -120.0000 29

  8 omega   57.00   98.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000 -180.0000 41

  9 omega   37.00  103.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000  120.0000 66

 10 omega   31.00  105.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000   30.0000 74

 11 omega   12.00  114.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5073   77.0000  -30.0000 102

 12 omega   17.00  111.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5073   57.0000  -90.0000 94

 13 omega    2.00   96.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5073 -125.0000   60.0000 94

 14 omega   78.00  124.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000    0.0000 46
;
_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      -0.0000529000
_diffrn_orient_matrix_UB_12      0.0307935000
_diffrn_orient_matrix_UB_13      -0.0591271000
_diffrn_orient_matrix_UB_21      -0.1129781000
_diffrn_orient_matrix_UB_22      0.0011357000
_diffrn_orient_matrix_UB_23      -0.0081825000
_diffrn_orient_matrix_UB_31      0.0003652000
_diffrn_orient_matrix_UB_32      0.3244291000
_diffrn_orient_matrix_UB_33      0.0056324000
_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  0.0757
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8613
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.250
_diffrn_reflns_theta_min         3.241
_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    3.141
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.658
_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    1.535
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2716
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.0197
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0899P)^2^+0.1524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2597
_reflns_number_total             3294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce02157c2.cif
_cod_data_source_block           2A
_cod_depositor_comments
'Adding full bibliography for 7226989--7226997.cif.'
_cod_original_cell_volume        1672.13(16)
_cod_database_code               7226991
_nottingham_internal_coll_name   OFFPLC
_nottingham_internal_coll_number 14313
_nottingham_internal_coll_client FFP/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '60.0000, 240.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczfp
_nottingham_internal_coll_date   06/01/2015
_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 16/08/2016
_nottingham_internal_solution_user pczfp
_nottingham_internal_refinement_date 16/08/2016
_nottingham_internal_refinement_user pczfp
_nottingham_internal_self_validation_date 18/08/2016
_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         'C18 H14 N2 O4 S2'
_chemical_oxdiff_usercomment
'OFFPLC #14313 GVA-452 120K, FOMBLIN FILM ON A MICROMOUNT FOR FFP/DBA'
_reflns_odcompleteness_completeness 99.97
_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:
 C15(H15A,H15B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              65458
_olex2_date_sample_data_collection 2015-01-06
_olex2_date_sample_submission    2014-12-19
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'