Thionated naphthalene diimides: tuneable chromophores for applications in photoactive dyads.
Pearce, Nicholas; Davies, E. Stephen; Horvath, Raphael; Pfeiffer, Constance R.; Sun, Xue-Zhong; Lewis, William; McMaster, Jonathan; George, Michael W.; Champness, Neil R.; Physical chemistry chemical physics : PCCP 20 (2018) 752–764; doi:10.1039/c7cp06952a

data_7229515
_publ_section_title
;
 Thionated naphthalene diimides: tuneable chromophores for applications in
 photoactive dyads.
;
_journal_issue                   2
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              752
_journal_page_last               764
_journal_paper_doi               10.1039/c7cp06952a
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H18 N2 S3'
_chemical_formula_sum            'C30 H18 N2 S3'
_chemical_formula_weight         502.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-08-25 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.3620(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.36487(18)
_cell_length_b                   9.88933(14)
_cell_length_c                   9.81295(15)
_cell_measurement_reflns_used    4132
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.9130
_cell_measurement_theta_min      4.4550
_cell_volume                     1162.43(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXT (Sheldrick, 2015)'
_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 0.959
_diffrn_measurement_details
;
  1 omega  -38.00    2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1851   38.0000   60.0000 40

  2 omega -118.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1851  -19.0000 -150.0000 102

  3 omega  -30.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1851   38.0000 -180.0000 56

  4 omega   54.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      103.6263 -125.0000  120.0000 68

  5 omega   64.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      103.6263  -30.0000  150.0000 25

  6 omega   53.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      103.6263  -77.0000  120.0000 66

  7 omega   35.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      103.6263  -30.0000    0.0000 55

  8 omega   61.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      103.6263  -30.0000  -90.0000 27

  9 omega   53.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      103.6263  -30.0000 -150.0000 26

 10 omega   81.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      103.6263   45.0000  -90.0000 39

 11 omega  121.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      103.6263   45.0000  -90.0000 48

 12 omega   36.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      103.6263  -30.0000   90.0000 55
;
_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      -0.0024933000
_diffrn_orient_matrix_UB_12      -0.0798625000
_diffrn_orient_matrix_UB_13      -0.1355964000
_diffrn_orient_matrix_UB_21      0.1070706000
_diffrn_orient_matrix_UB_22      -0.0753316000
_diffrn_orient_matrix_UB_23      0.0759422000
_diffrn_orient_matrix_UB_31      -0.0712222000
_diffrn_orient_matrix_UB_32      -0.1104470000
_diffrn_orient_matrix_UB_33      0.0461496000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4526
_diffrn_reflns_point_group_measured_fraction_full 0.674
_diffrn_reflns_point_group_measured_fraction_max 0.641
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.911
_diffrn_reflns_theta_min         4.471
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.091
_exptl_absorpt_correction_T_max  0.436
_exptl_absorpt_correction_T_min  0.227
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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 black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_preparation
'Prepared from the reaction between Lawesson's reagent and N-(10-phenyl-10H-phenothiazine)-1,8-naphthalic imide.'
_exptl_crystal_recrystallization_method
'Crystallised by vapour diffusion of pentane into a chloroform solution of the compound.'
_exptl_crystal_size_max          0.8971
_exptl_crystal_size_mid          0.5078
_exptl_crystal_size_min          0.3949
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.003(16)
_refine_ls_extinction_coef       0.0071(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0811P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.333
_reflns_Friedel_fraction_full    0.350
_reflns_Friedel_fraction_max     0.321
_reflns_number_gt                2981
_reflns_number_total             3017
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cp06952a2.cif
_cod_data_source_block           ntnmpj
_cod_depositor_comments
'Adding full bibliography for 7229515--7229521.cif.'
_cod_database_code               7229515
_nottingham_internal_coll_name   NTNMPJ
_nottingham_internal_coll_number 14809
_nottingham_internal_coll_client NMP/NRC
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time 1.0000
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pcxnp7
_nottingham_internal_coll_date   18/06/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 18/06/2015
_nottingham_internal_process_user pcxnp7
_nottingham_internal_solution_date 18/06/2015
_nottingham_internal_solution_user pcxnp7,pczcrp
_nottingham_internal_refinement_date 05/11/2016
_nottingham_internal_refinement_user pcxnp7,pczcrp
_nottingham_internal_self_archive_date 05/11/2016
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C30 H18 N2 S3'
_chemical_oxdiff_usercomment
'#14809 NTNMPJ IN FOMBLIN FILM ON MICROMOUNT GVA-602'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C20(H20), C21(H21), C27(H27), C24(H24), C18(H18), C6(H6), C17(H17),
 C7(H7), C3(H3), C5(H5), C31(H31), C26(H26), C25(H25), C32(H32), C4(H4),
 C34(H34), C33(H33)
;
_shelx_res_checksum              37551
_olex2_exptl_crystal_mounting_method 'In fomblin film on micromount.'
_olex2_submission_special_instructions 'No special instructions were received'