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_7226990
_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         'C22 H20 N2 O6 S2'
_chemical_formula_sum            'C22 H20 N2 O6 S2'
_chemical_formula_weight         472.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3622(8)
_cell_length_b                   5.6904(3)
_cell_length_c                   24.0819(10)
_cell_measurement_reflns_used    5392
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.9110
_cell_measurement_theta_min      5.7290
_cell_volume                     2105.17(18)
_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 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega -111.00  -18.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000 -150.0000 93

  2 omega -110.00  -27.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000  -60.0000 83

  3 omega   85.00  110.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7527 -144.0000  166.0000 25

  4 omega   88.00  172.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   45.0000 -120.0000 84

  5 omega   27.00  107.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -95.0000 -120.0000 80

  6 omega   43.00   89.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -30.0000 -180.0000 46

  7 omega   37.00   83.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -45.0000  -90.0000 46

  8 omega   39.00   81.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -45.0000 -120.0000 42

  9 omega   27.00  143.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -15.0000   60.0000 116

 10 omega -112.00   -7.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -77.0000  120.0000 105

 11 omega   23.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7527 -125.0000 -150.0000 75

 12 omega   76.00  178.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000  150.0000 102

 13 omega   27.00   95.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -95.0000   90.0000 68
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      0.0141136000
_diffrn_orient_matrix_UB_12      0.0501506000
_diffrn_orient_matrix_UB_13      0.0622294000
_diffrn_orient_matrix_UB_21      -0.0368646000
_diffrn_orient_matrix_UB_22      -0.2440186000
_diffrn_orient_matrix_UB_23      0.0143865000
_diffrn_orient_matrix_UB_31      0.0922113000
_diffrn_orient_matrix_UB_32      -0.1057465000
_diffrn_orient_matrix_UB_33      -0.0037659000
_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  0.0415
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10873
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.050
_diffrn_reflns_theta_min         5.760
_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    2.679
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.551
_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    1.491
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.3945
_exptl_crystal_size_mid          0.0762
_exptl_crystal_size_min          0.0311
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.31(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4159
_refine_ls_number_restraints     256
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0783
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+9.3841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2017
_refine_ls_wR_factor_ref         0.2026
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4055
_reflns_number_total             4159
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce02157c2.cif
_cod_data_source_block           1A
_cod_depositor_comments
'Adding full bibliography for 7226989--7226997.cif.'
_cod_original_cell_volume        2105.19(18)
_cod_database_code               7226990
_nottingham_internal_coll_name   OFFPLA
_nottingham_internal_coll_number 14283
_nottingham_internal_coll_client FFP/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '30.0000, 120.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczfp
_nottingham_internal_coll_date   16/01/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_date 19/01/2015
_nottingham_internal_process_user pczfp
_nottingham_internal_solution_date 19/1/2015
_nottingham_internal_solution_user pczfp
_nottingham_internal_refinement_date 19/1/2015
_nottingham_internal_refinement_user pczfp
_nottingham_internal_self_validation_date 10/5/2016
_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         'C22 H20 N2 O6 S2'
_chemical_oxdiff_usercomment
'OFFPLA#14283 - SN-380 - FOMBLIN FIBER ON A MICROMOUNT FOT FFP/DBA'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.69(5) 0.31(5)
2. 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
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C19(H19A,H19B), C21(H21A,H21B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C12(H12), C13(H13), C14(H14)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              57515
_olex2_date_sample_data_collection 2016-01-16
_olex2_date_sample_submission    2015-12-15
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'