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_7229518
_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         'C40 H33 N3 O S4'
_chemical_formula_sum            'C40 H33 N3 O S4'
_chemical_formula_weight         699.93
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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                 93.320(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.4330(9)
_cell_length_b                   14.3097(4)
_cell_length_c                   8.5187(3)
_cell_measurement_reflns_used    8401
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.5550
_cell_measurement_theta_min      2.5410
_cell_volume                     3338.47(19)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      150(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details
;
  1 omega  -72.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   10.0000    0.0000 188

  2 omega   -5.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  240.0000 67
;
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      -0.0240284000
_diffrn_orient_matrix_UB_12      0.0130460000
_diffrn_orient_matrix_UB_13      0.0063735000
_diffrn_orient_matrix_UB_21      -0.0075599000
_diffrn_orient_matrix_UB_22      -0.0429010000
_diffrn_orient_matrix_UB_23      -0.0294529000
_diffrn_orient_matrix_UB_31      0.0006370000
_diffrn_orient_matrix_UB_32      -0.0179462000
_diffrn_orient_matrix_UB_33      0.0752724000
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11575
_diffrn_reflns_point_group_measured_fraction_full 0.809
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_theta_full        24.207
_diffrn_reflns_theta_max         24.207
_diffrn_reflns_theta_min         2.565
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73999
_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    1.393
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_preparation
'Synthesised by the reaction of (a-aminophenyl)-10H-phenothiazine with N-(octyl)naphthalene-1,8-imide-3,4-anhydride in molten imidazole.'
_exptl_crystal_recrystallization_method
'Crystallised by vapour diffusion of hexane into a chloroform solution of compound'
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 3621 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.36(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     867
_refine_ls_number_reflns         9537
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0526P)^2^+1.1280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.690
_reflns_Friedel_fraction_max     0.690
_reflns_number_gt                9050
_reflns_number_total             9537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cp06952a2.cif
_cod_data_source_block           ntnmph
_cod_depositor_comments
'Adding full bibliography for 7229515--7229521.cif.'
_cod_original_cell_volume        3338.45(19)
_cod_database_code               7229518
_nottingham_internal_coll_name   NTNMPH
_nottingham_internal_coll_number 14645
_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   pczajb
_nottingham_internal_coll_date   19/4/2015
_nottingham_internal_coll_location DLS
_nottingham_internal_coll_instrument 'EH1, I19, DLS'
_nottingham_internal_process_date 22/4/2015
_nottingham_internal_process_user pcxnp7
_nottingham_internal_solution_date 22/4/2015
_nottingham_internal_solution_user pcxnp7
_nottingham_internal_refinement_date 5/11/2015
_nottingham_internal_refinement_user pczcrp/pcxnp7
_nottingham_internal_self_archive_date 6/11/2015
_nottingham_internal_self_validation_date 6/11/2015
_nottingham_internal_self_validation_user pczcrp
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C40 H33 N3 O1 S4'
_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:
 C41A(H41a,H41b), C42A(H42a,H42b), C43A(H43a,H43b), C44A(H44a,H44b), C45A(H45a,
 H45b), C46A(H46a,H46b), C47A(H47a,H47b), C41B(H41c,H41d), C42B(H42c,H42d),
 C43B(H43c,H43d), C44B(H44c,H44d), C45B(H45c,H45d), C46B(H46c,H46d), C47B(H47c,
 H47d)
2.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C6A(H6A), C7A(H7A), C22A(H22A), C23A(H23A), C25A(H25A),
 C26A(H26A), C29A(H29A), C30A(H30A), C31A(H31A), C32A(H32A), C36A(H36A),
 C37A(H37A), C38A(H38A), C39A(H39A), C2B(H2B), C3B(H3B), C6B(H6B), C7B(H7B),
 C22B(H22B), C23B(H23B), C25B(H25B), C26B(H26B), C29B(H29B), C30B(H30B),
 C31B(H31B), C32B(H32B), C36B(H36B), C37B(H37B), C38B(H38B), C39B(H39B)
2.c Idealised Me refined as rotating group:
 C48A(H48a,H48b,H48c), C48B(H48d,H48e,H48f)
;
_shelx_res_checksum              73360
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'