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_7226993
_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         'C25 H27 Br N2 O4 S2'
_chemical_formula_sum            'C25 H27 Br N2 O4 S2'
_chemical_formula_weight         563.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1252(4)
_cell_length_b                   14.6758(4)
_cell_length_c                   34.2996(9)
_cell_measurement_reflns_used    22173
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.4560
_cell_measurement_theta_min      2.2440
_cell_volume                     5096.8(3)
_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_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_details
;
  1 omega  -60.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000    0.0000    0.0000 175

  2 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000    0.0000 120

  3 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  120.0000 120

  4 omega  -60.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  240.0000 119
;
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0134479000
_diffrn_orient_matrix_UB_12      0.0053174000
_diffrn_orient_matrix_UB_13      0.0195377000
_diffrn_orient_matrix_UB_21      -0.0096056000
_diffrn_orient_matrix_UB_22      0.0462915000
_diffrn_orient_matrix_UB_23      -0.0017374000
_diffrn_orient_matrix_UB_31      -0.0660359000
_diffrn_orient_matrix_UB_32      -0.0056403000
_diffrn_orient_matrix_UB_33      0.0042832000
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            61833
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         31.621
_diffrn_reflns_theta_min         2.302
_diffrn_source                   synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45945
_exptl_absorpt_correction_type   multi-scan
_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)
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    1.469
_exptl_crystal_description       plate
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.151
_refine_diff_density_min         -1.738
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         8750
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1320P)^2^+5.9072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2206
_refine_ls_wR_factor_ref         0.2391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6702
_reflns_number_total             8750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce02157c2.cif
_cod_data_source_block           1CD
_cod_depositor_comments
'Adding full bibliography for 7226989--7226997.cif.'
_cod_database_code               7226993
_nottingham_internal_coll_name   OFFPLO
_nottingham_internal_coll_number 14776
_nottingham_internal_coll_client FFP/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   26/06/2015
_nottingham_internal_coll_location DLS
_nottingham_internal_process_date 18/04/2016
_nottingham_internal_process_user pzcfp/pczwl
_nottingham_internal_solution_date 18/04/2016
_nottingham_internal_solution_user pczfp/pczwl
_nottingham_internal_refinement_date 18/08/2016
_nottingham_internal_refinement_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         'C25 H27 Br N2 O4 S2'
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.50
_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
 C11-C12A \\sim C11-C12 \\sim C1A-C4 \\sim C1-C4
 with sigma of 0.02
 S2A-C11 \\sim S2-C11 \\sim S1-C4 \\sim S1A-C4
 with sigma of 0.02
 S1-C3 \\sim S1A-C2 \\sim S2A-C13 \\sim S2-C14
 with sigma of 0.02
 C12-C13 \\sim C12A-C14 \\sim C1-C2 \\sim C1A-C3
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 S1, S1A, C1, C1A, C2, C3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S2, S2A, C11, C12, C12A, C13, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(S1A)=Sof(C1A)=Sof(H1A)=Sof(H2b)=Sof(H3b)=1-FVAR(1)
 Sof(S1)=Sof(C1)=Sof(H1)=Sof(H2a)=Sof(H3a)=FVAR(1)
 Sof(S2A)=Sof(C12A)=Sof(H12A)=Sof(H13a)=Sof(H14a)=1-FVAR(2)
 Sof(S2)=Sof(C12)=Sof(H12)=Sof(H13)=Sof(H14)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C20(H20a,H20b), C21(H21a,H21b), C22(H22a,H22b), C23(H23a,H23b), C24(H24a,
 H24b), C25(H25a,H25b)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C1A(H1A), C2(H2a), C2(H2b), C3(H3a), C3(H3b), C12(H12), C12A(H12A),
 C13(H13), C13(H13a), C14(H14), C14(H14a)
5.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c)
;
_shelx_res_checksum              78997
_olex2_date_sample_data_collection 2015-06-26
_olex2_date_sample_submission    2015-05-07
_olex2_exptl_crystal_mounting_method 'IN FOMBLIN FILM ON A MICROMOUNT'
_olex2_submission_special_instructions 'No special instructions were received'