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_7226989
_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         'C24 H24 N2 O6 S2'
_chemical_formula_sum            'C24 H24 N2 O6 S2'
_chemical_formula_weight         500.57
_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
_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                 100.970(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8589(3)
_cell_length_b                   20.0100(12)
_cell_length_c                   10.2562(5)
_cell_measurement_reflns_used    2032
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0070
_cell_measurement_theta_min      4.3940
_cell_volume                     1180.43(11)
_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 0.990
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
  1 omega  -79.00  -15.00   1.0000    3.1200
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000  120.0000 64

  2 omega   36.00   81.00   1.0000   12.4900
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  -60.0000 45

  3 omega   51.00   89.00   1.0000   12.4900
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000    0.0000 38

  4 omega   89.00  174.00   1.0000   12.4900
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   30.0000 85

  5 omega   53.00   98.00   1.0000   12.4900
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000 -120.0000 45

  6 omega   48.00  114.00   1.0000   12.4900
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000 -150.0000 66

  7 omega   35.00  103.00   1.0000   12.4900
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000  -90.0000 68

  8 omega   28.00   93.00   1.0000   12.4900
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000   60.0000 65

  9 omega   -2.00  114.00   1.0000    3.1200
omega____ theta____ kappa____ phi______ frames
    -       42.2573    0.0000 -180.0000 116
;
_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      -0.0355624000
_diffrn_orient_matrix_UB_12      -0.0747276000
_diffrn_orient_matrix_UB_13      0.0261059000
_diffrn_orient_matrix_UB_21      -0.2620464000
_diffrn_orient_matrix_UB_22      0.0122538000
_diffrn_orient_matrix_UB_23      -0.0090506000
_diffrn_orient_matrix_UB_31      -0.0420045000
_diffrn_orient_matrix_UB_32      -0.0136610000
_diffrn_orient_matrix_UB_33      -0.1505928000
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4366
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.245
_diffrn_reflns_theta_min         4.419
_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    2.420
_exptl_absorpt_correction_T_max  0.807
_exptl_absorpt_correction_T_min  0.424
_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            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.3528
_exptl_crystal_size_mid          0.1907
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2283
_refine_ls_number_restraints     121
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0611P)^2^+0.3734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2019
_reflns_number_total             2283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce02157c2.cif
_cod_data_source_block           1C
_cod_depositor_comments
'Adding full bibliography for 7226989--7226997.cif.'
_cod_original_cell_volume        1180.42(11)
_cod_database_code               7226989
_nottingham_internal_coll_name   OFFPLI
_nottingham_internal_coll_number 14432
_nottingham_internal_coll_client FFP/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '3.1200, 12.4900'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczfp
_nottingham_internal_coll_date   12/02/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 12/02/2015
_nottingham_internal_process_user pczfp
_nottingham_internal_solution_date 12/2/2015
_nottingham_internal_solution_user pczfp
_nottingham_internal_refinement_date 12/2/2015
_nottingham_internal_refinement_user pczfp
_nottingham_internal_self_validation_date 10/5/2016
_nottingham_internal_self_validation_user pczfp
_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 H24 N2 O6 S2'
_chemical_oxdiff_usercomment
'OFFPLA # 14432 GVA-494 FOMBLIN FILM ON A MICROMOUNT FOR FFP/DBA'
_reflns_odcompleteness_completeness 99.49
_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. Restrained distances
 C4-C3A \\sim C4-C3
 with sigma of 0.02
 C3A-C1 \\sim C3-C2
 with sigma of 0.02
 S1A-C4 \\sim S1-C4
 with sigma of 0.02
 S1-C1 \\sim S1A-C2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S1 \\sim S1A \\sim C1 \\sim C2 \\sim C3 \\sim C3A \\sim C4: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 S1, S1A, C1, C2, C3, C3A, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(S1A)=Sof(H1B)=Sof(H2B)=Sof(C3A)=Sof(H3A)=1-FVAR(1)
 Sof(S1)=Sof(H1A)=Sof(H2A)=Sof(C3)=Sof(H3)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C1(H1B), C2(H2A), C2(H2B), C3(H3), C3A(H3A)
6.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              52441
_olex2_date_sample_data_collection 2015-02-12
_olex2_date_sample_submission    2015-02-04
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'