Thionated perylene diimides with intense absorbance in the near-IR.
Llewellyn, Ben A.; Davies, E. Stephen; Pfeiffer, Constance R.; Cooper, Mick; Lewis, William; Champness, Neil R.; Chemical communications (Cambridge, England) 52 (2016) 2099–2102; doi:10.1039/c5cc09962e

data_7118635
_publ_section_title
;
 Thionated perylene diimides with intense absorbance in the near-IR.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2099
_journal_page_last               2102
_journal_paper_doi               10.1039/c5cc09962e
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C40 H40 N4 O6'
_chemical_formula_sum            'C40 H40 N4 O6'
_chemical_formula_weight         672.76
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-03
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2015-11-03 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.6840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7735(2)
_cell_length_b                   8.38150(10)
_cell_length_c                   32.1723(5)
_cell_measurement_reflns_used    7387
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.9780
_cell_measurement_theta_min      3.7330
_cell_volume                     3200.66(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3271
_diffrn_measured_fraction_theta_full 0.9948
_diffrn_measured_fraction_theta_max 0.9670
_diffrn_measurement_details
;
  1 omega  -63.00   29.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2611   57.0000 -120.0000 92

  2 omega  -30.00   34.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5000   30.0000  -60.0000 64

  3 omega  -13.00   32.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5000   30.0000  150.0000 45

  4 omega   29.00   68.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6753  -77.0000   60.0000 39

  5 omega   79.00  170.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6753   44.0000 -162.0000 91

  6 omega   28.00   91.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6753  -30.0000   60.0000 63

  7 omega   36.00   84.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6753  -45.0000 -180.0000 48

  8 omega   41.00   87.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6753  -45.0000  -90.0000 46

  9 omega   86.00  124.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6753  -77.0000   60.0000 38

 10 omega   45.00   73.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6753  -77.0000 -180.0000 28

 11 omega   88.00  129.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6753  -77.0000 -180.0000 41

 12 omega   31.00   91.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6753  -30.0000 -150.0000 60
;
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0137329000
_diffrn_orient_matrix_UB_12      -0.0526243000
_diffrn_orient_matrix_UB_13      0.0488295000
_diffrn_orient_matrix_UB_21      -0.1065218000
_diffrn_orient_matrix_UB_22      0.0859828000
_diffrn_orient_matrix_UB_23      0.0004867000
_diffrn_orient_matrix_UB_31      -0.0550051000
_diffrn_orient_matrix_UB_32      -0.1536862000
_diffrn_orient_matrix_UB_33      -0.0164512000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            12505
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.141
_diffrn_reflns_theta_min         2.956
_diffrn_source                   'GV1000 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  1.141
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.8185
_exptl_crystal_size_mid          0.1668
_exptl_crystal_size_min          0.0353
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0725P)^2^+1.3668P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5701
_reflns_number_total             6283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09962e2.cif
_cod_data_source_block           perbld
_cod_database_code               7118635
_nottingham_internal_coll_name   PERBLD
_nottingham_internal_coll_number 12778
_nottingham_internal_coll_client BL/NRC
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '20 and 80s'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   BL/SPA
_nottingham_internal_coll_date   28/08/2013
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user SPA/BL
_nottingham_internal_process_date 29/08/2013
_nottingham_internal_solution_user BL
_nottingham_internal_solution_date 03/09/2013
_nottingham_internal_refinement_user SPA/BL
_nottingham_internal_refinement_date 03/09/2013
_chemical_oxdiff_formula         'C40 H40 N4 O6'
_chemical_oxdiff_usercomment
'PERBLD #12778 for BL/NC on micromount in fomblin'
_reflns_odcompleteness_completeness 99.48
_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.a Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C33(H33A,H33B), C35(H35A,H35B), C36(H36A,H36B), C42(H42A,
 H42B), C43(H43A,H43B), C45(H45A,H45B), C46(H46A,H46B), C51(H51A,H51B),
 C52(H52A,H52B), C53(H53A,H53B), C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C54(H54A,H54B,H54C), C64(H64A,H64B,H64C)
;
_shelxl_version_number           2012-9