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_7226995
_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         '2(C20 H19 Br N2 O2 S2)'
_chemical_formula_sum            'C40 H38 Br2 N4 O4 S4'
_chemical_formula_weight         926.80
_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                 99.5359(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.18976(10)
_cell_length_b                   14.54422(15)
_cell_length_c                   26.2201(3)
_cell_measurement_reflns_used    34173
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.1180
_cell_measurement_theta_min      3.0350
_cell_volume                     3832.18(7)
_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 0.992
_diffrn_measurement_details
;
  1 omega   -9.00   80.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573  -99.0000   60.0000 89

  2 omega  -25.00    2.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573  -38.0000 -120.0000 27

  3 omega   38.00   63.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573  -38.0000 -120.0000 25

  4 omega   23.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   38.0000 -120.0000 76

  5 omega   40.00   98.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  120.0000 58

  6 omega   37.00   91.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  -30.0000 54

  7 omega   41.00   95.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  -90.0000 54

  8 omega   63.00   90.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   60.0000 27

  9 omega   64.00  101.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000 -180.0000 37

 10 omega   55.00   82.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000 -180.0000 27

 11 omega   63.00   90.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000 -150.0000 27

 12 omega   82.00  153.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000 -120.0000 71

 13 omega   36.00  121.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000  120.0000 85

 14 omega   22.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   38.0000  -30.0000 92

 15 omega   18.00  111.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   57.0000  120.0000 93

 16 omega   18.00  111.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   57.0000   30.0000 93

 17 omega   82.00  174.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  150.0000 92

 18 omega   74.00  176.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -90.0000 102

 19 omega   82.00  174.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000    0.0000 92

 20 omega   74.00  176.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -180.0000 102

 21 omega   25.00  109.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000  -90.0000 84

 22 omega   82.00  174.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   60.0000 92

 23 omega   13.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   77.0000  120.0000 101

 24 omega   13.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   77.0000 -150.0000 101

 25 omega    2.00   97.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573 -125.0000  -90.0000 95

 26 omega   74.00  176.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -60.0000 102

 27 omega   27.00  111.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -99.0000  114.0000 84

 28 omega   74.00  176.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000    0.0000 102

 29 omega   25.00  109.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000    0.0000 84

 30 omega   74.00  176.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -120.0000 102

 31 omega   78.00  173.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000   90.0000 95

 32 omega  -50.00  -15.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000 -180.0000 35

 33 omega   13.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   77.0000   30.0000 101

 34 omega   13.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   77.0000  -60.0000 101
;
_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      0.0334879000
_diffrn_orient_matrix_UB_12      -0.0980912000
_diffrn_orient_matrix_UB_13      -0.0159149000
_diffrn_orient_matrix_UB_21      0.1494445000
_diffrn_orient_matrix_UB_22      0.0206509000
_diffrn_orient_matrix_UB_23      0.0159449000
_diffrn_orient_matrix_UB_31      -0.0060418000
_diffrn_orient_matrix_UB_32      -0.0341481000
_diffrn_orient_matrix_UB_33      0.0551883000
_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  0.0312
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            64282
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.121
_diffrn_reflns_theta_min         3.418
_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    5.116
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.467
_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    1.606
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.4188
_exptl_crystal_size_mid          0.0628
_exptl_crystal_size_min          0.0367
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         7735
_refine_ls_number_restraints     111
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0637P)^2^+2.1038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7222
_reflns_number_total             7735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce02157c2.cif
_cod_data_source_block           2D
_cod_depositor_comments
'Adding full bibliography for 7226989--7226997.cif.'
_cod_original_cell_volume        3832.17(7)
_cod_database_code               7226995
_nottingham_internal_coll_name   OFFPLF
_nottingham_internal_coll_number 14356
_nottingham_internal_coll_client FFP/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '8.0000, 32.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczfp
_nottingham_internal_coll_date   27/01/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 28/01/2015
_nottingham_internal_process_user pczfp
_nottingham_internal_solution_date 28/01/2015
_nottingham_internal_solution_user pczfp
_nottingham_internal_refinement_date 28/01/2015
_nottingham_internal_refinement_user pczfp
_nottingham_internal_self_validation_date 16/08/2016
_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         'C40 H38 Br2 N4 O4 S4'
_chemical_oxdiff_usercomment
'OFFPLF # 14356 GVA-470 Fomblin film on a micromount fpr FFP/DBA'
_reflns_odcompleteness_completeness 99.99
_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
2. Restrained distances
 N2B-H2B = N2A-H2A
 0.84 with sigma of 0.02
 S2AA-C11A \\sim S2A-C11A
 with sigma of 0.02
 C12A-C11A \\sim C11A-C12C
 with sigma of 0.02
 C13A-C12A \\sim C14A-C12C
 with sigma of 0.02
 S2AA-C13A \\sim S2A-C14A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S2A \\sim S2AA \\sim C11A \\sim C12A \\sim C12C \\sim C13A \\sim C14A: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 S2A, S2AA, C11A, C12A, C12C, C13A, C14A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(S2AA)=Sof(C12C)=Sof(H12C)=Sof(H13B)=Sof(H14B)=1-FVAR(1)
 Sof(S2A)=Sof(C12A)=Sof(H12A)=Sof(H13A)=Sof(H14A)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C15A(H15A,H15B), C16A(H16A,H16B), C17A(H17A,H17B), C18A(H18A,H18B), C19A(H19A,
 H19B), C20A(H20A,H20B), C15B(H15C,H15D), C16B(H16C,H16D), C17B(H17C,H17D),
 C18B(H18C,H18D), C19B(H19C,H19D), C20B(H20C,H20D)
6.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2AA), C3A(H3A), C12A(H12A), C12C(H12C), C13A(H13A), C13A(H13B),
  C14A(H14A), C14A(H14B), C1B(H1B), C2B(H2BA), C3B(H3B), C12B(H12B), C13B(H13C),
  C14B(H14C)
;
_shelx_res_checksum              31253
_olex2_date_sample_data_collection 2015-01-27
_olex2_date_sample_submission    2015-01-08
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'