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_7226992
_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 syn
_chemical_formula_moiety         'C19 H18 N2 O2 S2'
_chemical_formula_sum            'C19 H18 N2 O2 S2'
_chemical_formula_weight         370.47
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3'
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-05
_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                120
_cell_formula_units_Z            18
_cell_length_a                   39.546(4)
_cell_length_b                   39.546(4)
_cell_length_c                   5.9306(8)
_cell_measurement_reflns_used    5825
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.5900
_cell_measurement_theta_min      3.8550
_cell_volume                     8032.2(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41n (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41n (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41n (Rigaku OD, 2015)'
_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                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -33.00  33.00   1.00   60.00    --    0.00 -82.00-180.00   66
  2  \w    -33.00  33.00   1.00   60.00    --    0.00 -82.00-150.00   66
  3  \w     13.00  71.00   1.00  240.00    --  102.10 -38.00-120.00   58
  4  \w     13.00  71.00   1.00  240.00    --  102.10 -38.00 -60.00   58
  5  \w     13.00 134.00   1.00  240.00    --  102.10 -19.00  30.00  121
  6  \w     13.00  71.00   1.00  240.00    --  102.10 -38.00 -90.00   58
  7  \w     13.00  71.00   1.00  240.00    --  102.10 -38.00  60.00   58
  8  \w     13.00  71.00   1.00  240.00    --  102.10 -38.00  30.00   58
  9  \w     79.00 191.00   1.00  240.00    --  102.10  38.00 150.00  112
 10  \w    -89.00  32.00   1.00   60.00    --    0.00 -19.00 -60.00  121
 11  \w    -89.00  23.00   1.00   60.00    --    0.00 -38.00  60.00  112
 12  \w     13.00  71.00   1.00  240.00    --  102.10 -38.00-180.00   58
 13  \w     13.00 135.00   1.00  240.00    --  102.10 -82.00-180.00  122
 14  \w     74.00 133.00   1.00  240.00    --  102.10  66.00-167.00   59
 15  \w     70.00 191.00   1.00  240.00    --  102.10  19.00  60.00  121
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0097891000
_diffrn_orient_matrix_UB_12      -0.0289941000
_diffrn_orient_matrix_UB_13      -0.1953862000
_diffrn_orient_matrix_UB_21      0.0031836000
_diffrn_orient_matrix_UB_22      0.0312895000
_diffrn_orient_matrix_UB_23      -0.1689168000
_diffrn_orient_matrix_UB_31      0.0436803000
_diffrn_orient_matrix_UB_32      0.0140959000
_diffrn_orient_matrix_UB_33      -0.0311191000
_diffrn_radiation_collimation    'VariMax VHF mirror optic'
_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  0.0908
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            22325
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.490
_diffrn_reflns_theta_min         3.872
_diffrn_source                   'rotating anode'
_diffrn_source_current           30
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'MicroMax 007 HF'
_diffrn_source_voltage           40
_exptl_absorpt_coefficient_mu    2.827
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41n (Rigaku Oxford Diffraction, 2015)
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    1.379
_exptl_crystal_description       needle
_exptl_crystal_F_000             3492
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.20(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         6948
_refine_ls_number_restraints     1176
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0837
_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^)+(0.1832P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2238
_refine_ls_wR_factor_ref         0.2655
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4195
_reflns_number_total             6948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce02157c2.cif
_cod_data_source_block           2E
_cod_depositor_comments
'Adding full bibliography for 7226989--7226997.cif.'
_cod_original_cell_volume        8032.0(18)
_cod_database_code               7226992
_nottingham_internal_coll_name   OFFPLQ
_nottingham_internal_coll_number 14923
_nottingham_internal_coll_client FFP/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'ofand \w scans'
_nottingham_internal_coll_frame_time 'degrees,, 60.00, 240.00'
_nottingham_internal_coll_frame_width 'in, 1.00'
_nottingham_internal_coll_user   pczfp
_nottingham_internal_coll_date   15/01/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_process_date 20/01/2016
_nottingham_internal_process_user pczfp
_nottingham_internal_solution_date 20/01/2016
_nottingham_internal_solution_user pczfp
_nottingham_internal_refinement_date 20/01/2016
_nottingham_internal_refinement_user pczfp
_nottingham_internal_self_validation_date 16/08/2016
_nottingham_internal_self_validation_user pczfp/pczwl
_nottingham_internal_validation_date 5/10/2016
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 5/10/2016
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C19H18N2O2S2
_chemical_oxdiff_usercomment
'OFFPLQ #14923 MM-19 IN FOMBLIN FILM ON A MICROMOUNT FOR FFP/DBA'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.80(6) 0.20(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C11A-C12C \\sim C11A-C12A
 with sigma of 0.02
 S2A-C11A \\sim S2C-C11A
 with sigma of 0.02
 C11A-C12A \\sim C11A-C12C
 with sigma of 0.02
 C13A-C12A \\sim C14A-C12C
 with sigma of 0.02
 S2C-C13A \\sim S2A-C14A
 with sigma of 0.02
 C14A-C12C \\sim C13A-C12A
 with sigma of 0.02
 C14A-C12C \\sim C14A-C13A
 with sigma of 0.02
 C4B-C3B \\sim C11B-C12D \\sim C11B-C12B
 with sigma of 0.02
 S1B-C1B \\sim S2B-C14B \\sim S2D-C13B
 with sigma of 0.02
 C2B-C3B \\sim C12D-C14B \\sim C13B-C12B
 with sigma of 0.02
 S1B-C4B \\sim S2D-C11B \\sim S2B-C11B
 with sigma of 0.02
 S1B-C1B \\sim S2D-C13B \\sim S2B-C14B
 with sigma of 0.02
 C1B-C2B \\sim C13B-C14B
 with sigma of 0.02
 C16B-C18B \\sim C18B-C19B
 with sigma of 0.02
 N1B-C15B \\sim N1B-C15D \\sim N1A-C15A
 with sigma of 0.02
 C16B-C15B \\sim C16D-C15D \\sim C16A-C15A \\sim C16C-C15A
 with sigma of 0.02
 C18D-C16D \\sim C18B-C16B \\sim C18C-C16C \\sim C18A-C16A
 with sigma of 0.02
 C19C-C18C \\sim C19A-C18A \\sim C19D-C18D \\sim C19B-C18B
 with sigma of 0.02
 C16D-C19D \\sim C16B-C19B \\sim C16C-C19C \\sim C16A-C19A
 with sigma of 0.02
 C17D-C16D \\sim C17B-C16B \\sim C17A-C16A \\sim C17C-C16C
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
5. 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
6. Others
 Sof(S2D)=Sof(C12D)=Sof(H12D)=Sof(H13A)=Sof(H14A)=1-FVAR(1)
 Sof(S2B)=Sof(C12B)=Sof(H12B)=Sof(H13B)=Sof(H14B)=FVAR(1)
 Sof(S2C)=Sof(C12C)=Sof(H12C)=Sof(H13D)=Sof(H14D)=1-FVAR(2)
 Sof(S2A)=Sof(C12A)=Sof(H12A)=Sof(H13C)=Sof(H14C)=FVAR(2)
 Sof(H15G)=Sof(H15H)=Sof(C16C)=Sof(H16C)=Sof(C17C)=Sof(H17J)=Sof(H17K)=
 Sof(H17L)=Sof(C18C)=Sof(H18G)=Sof(H18H)=Sof(C19C)=Sof(H19J)=Sof(H19K)=
 Sof(H19L)=1-FVAR(3)
 Sof(H15E)=Sof(H15F)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17G)=Sof(H17H)=
 Sof(H17I)=Sof(C18A)=Sof(H18E)=Sof(H18F)=Sof(C19A)=Sof(H19G)=Sof(H19H)=
 Sof(H19I)=FVAR(3)
 Sof(C15D)=Sof(H15C)=Sof(H15D)=Sof(C16D)=Sof(H16D)=Sof(C17D)=Sof(H17D)=
 Sof(H17E)=Sof(H17F)=Sof(C18D)=Sof(H18C)=Sof(H18D)=Sof(C19D)=Sof(H19D)=
 Sof(H19E)=Sof(H19F)=1-FVAR(4)
 Sof(C15B)=Sof(H15A)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17A)=
 Sof(H17B)=Sof(H17C)=Sof(C18B)=Sof(H18A)=Sof(H18B)=Sof(C19B)=Sof(H19A)=
 Sof(H19B)=Sof(H19C)=FVAR(4)
7.a Ternary CH refined with riding coordinates:
 C16A(H16A), C16C(H16C), C16B(H16B), C16D(H16D)
7.b Secondary CH2 refined with riding coordinates:
 C15A(H15E,H15F), C15A(H15G,H15H), C18A(H18E,H18F), C18C(H18G,H18H), C15B(H15A,
 H15B), C15D(H15C,H15D), C18B(H18A,H18B), C18D(H18C,H18D)
7.c Me refined with riding coordinates:
 C17D(H17D,H17E,H17F)
7.d Aromatic/amide H refined with riding coordinates:
 N2A(H2A), C1A(H1A), C2A(H2AA), C3A(H3A), C12A(H12A), C12C(H12C), C13A(H13C),
 C13A(H13D), C14A(H14C), C14A(H14D), N2B(H2B), C1B(H1B), C2B(H2BA), C3B(H3B),
 C12B(H12B), C12D(H12D), C13B(H13B), C13B(H13A), C14B(H14B), C14B(H14A)
7.e Idealised Me refined as rotating group:
 C17A(H17G,H17H,H17I), C17C(H17J,H17K,H17L), C19A(H19G,H19H,H19I), C19C(H19J,
 H19K,H19L), C17B(H17A,H17B,H17C), C19B(H19A,H19B,H19C), C19D(H19D,H19E,H19F)
;
_shelx_res_checksum              77950
_olex2_date_sample_data_collection 2016-01-15
_olex2_date_sample_submission    2015-07-29
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.725
_oxdiff_exptl_absorpt_empirical_full_min 0.319