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_7118634
_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 O2 S4, C H Cl3'
_chemical_formula_sum            'C41 H41 Cl3 N4 O2 S4'
_chemical_formula_weight         856.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-11-03 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                93.393(5)
_cell_angle_beta                 105.711(5)
_cell_angle_gamma                107.519(5)
_cell_formula_units_Z            2
_cell_length_a                   10.5929(5)
_cell_length_b                   13.3915(8)
_cell_length_c                   15.0416(8)
_cell_measurement_reflns_used    5529
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.9070
_cell_measurement_theta_min      4.2720
_cell_volume                     1935.6(2)
_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, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
  1 omega   29.00  112.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       42.8101   38.0000   30.0000 83

  2 omega  113.00  175.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   30.0000  150.0000 62

  3 omega   47.00   82.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000  120.0000 35

  4 omega   36.00   85.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000   60.0000 49

  5 omega   38.00  116.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000  -30.0000 78

  6 omega   37.00   89.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000 -150.0000 52

  7 omega   41.00  171.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000    0.0000  -60.0000 130

  8 omega   37.00   83.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  -30.0000 46

  9 omega   23.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000   90.0000 86

 10 omega   33.00  121.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000    0.0000 88

 11 omega   27.00   98.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000 -120.0000 71

 12 omega   23.00  101.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000 -180.0000 78

 13 omega   20.00   51.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       42.8101   57.0000    0.0000 31

 14 omega  -28.00   65.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       42.8101  -38.0000 -150.0000 93

 15 omega  -22.00   73.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       42.8101  -77.0000  120.0000 95

 16 omega  -96.00  -68.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.8101  125.0000   90.0000 28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      -0.0472144000
_diffrn_orient_matrix_UB_12      -0.1189055000
_diffrn_orient_matrix_UB_13      0.0077524000
_diffrn_orient_matrix_UB_21      0.0054836000
_diffrn_orient_matrix_UB_22      0.0272868000
_diffrn_orient_matrix_UB_23      0.1022203000
_diffrn_orient_matrix_UB_31      -0.1528178000
_diffrn_orient_matrix_UB_32      -0.0044651000
_diffrn_orient_matrix_UB_33      -0.0329108000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14080
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.263
_diffrn_reflns_theta_min         4.302
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.506
_exptl_absorpt_correction_T_max  0.835
_exptl_absorpt_correction_T_min  0.656
_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            'dull black'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.1219
_exptl_crystal_size_mid          0.1097
_exptl_crystal_size_min          0.0549
_refine_diff_density_max         0.930
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7626
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0605
_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^)+(0.0889P)^2^+1.4749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1664
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6234
_reflns_number_total             7626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09962e2.cif
_cod_data_source_block           perbln
_cod_original_cell_volume        1935.59(19)
_cod_database_code               7118634
_nottingham_internal_coll_name   PERBLN
_nottingham_internal_coll_number 15170
_nottingham_internal_coll_client BL/NRC
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '12.5000, 50.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pcxbl1
_nottingham_internal_coll_date   21/09/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 22/09/2015
_nottingham_internal_process_user pcxbl1
_nottingham_internal_solution_date 22/09/15
_nottingham_internal_solution_user BL
_nottingham_internal_refinement_date 22/09/15
_nottingham_internal_refinement_user BL
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C41H41N4O2S4Cl3
_chemical_oxdiff_usercomment
'#15170, PERBLM, on micromount in fomblin, for BL/NRC '
_reflns_odcompleteness_completeness 99.81
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C54A-C53A \\sim C54-C53
 with sigma of 0.02
 C53-C52 \\sim C53A-C52
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C52, C53, C53, C54, C54
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C52, C53, C53A, C54, C54A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H52c)=Sof(H52d)=Sof(C53A)=Sof(H53c)=Sof(H53d)=Sof(C54A)=Sof(H54d)=
 Sof(H54e)=Sof(H54f)=1-FVAR(1)
 Sof(H52a)=Sof(H52b)=Sof(C53)=Sof(H53a)=Sof(H53b)=Sof(C54)=Sof(H54a)=Sof(H54b)=
 Sof(H54c)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1A(H1A)
5.b 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), C52(H52c,H52d), C53(H53a,H53b), C53A(H53c,H53d), C61(H61a,
 H61b), C62(H62a,H62b), C63(H63a,H63b)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12)
5.d Idealised Me refined as rotating group:
 C54(H54a,H54b,H54c), C54A(H54d,H54e,H54f), C64(H64a,H64b,H64c)
;
_shelx_res_checksum              86330
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'