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_7229519
_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_formula_moiety         'C24 H26 N2 O2 S2'
_chemical_formula_sum            'C24 H26 N2 O2 S2'
_chemical_formula_weight         438.59
_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     iterative
_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                 92.537(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7955(3)
_cell_length_b                   9.4770(4)
_cell_length_c                   12.8838(5)
_cell_measurement_reflns_used    1985
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0780
_cell_measurement_theta_min      5.7680
_cell_volume                     1072.88(7)
_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    '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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3271
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
  1 omega   22.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5073   37.0000   90.0000 76

  2 omega   53.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5073   57.0000  150.0000 58

  3 omega   49.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5073   37.0000  120.0000 60

  4 omega   45.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000  120.0000 45

  5 omega   91.00  118.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -61.0000  120.0000 27

  6 omega   47.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000   90.0000 62

  7 omega   58.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000  -30.0000 30

  8 omega   84.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   30.0000  -60.0000 87

  9 omega   83.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  150.0000 25

 10 omega  127.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  150.0000 38

 11 omega   43.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -61.0000  120.0000 35

 12 omega   31.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   30.0000 53

 13 omega   31.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000 -180.0000 38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      0.1736926000
_diffrn_orient_matrix_UB_12      -0.0026810000
_diffrn_orient_matrix_UB_13      0.0213536000
_diffrn_orient_matrix_UB_21      -0.0225546000
_diffrn_orient_matrix_UB_22      -0.0660977000
_diffrn_orient_matrix_UB_23      0.1074437000
_diffrn_orient_matrix_UB_31      0.0072214000
_diffrn_orient_matrix_UB_32      -0.1483598000
_diffrn_orient_matrix_UB_33      -0.0484913000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4286
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.375
_diffrn_reflns_theta_min         5.033
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.436
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_correction_T_min  0.652
_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 brownish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_preparation
'Slow evapouration of a chloroform/hexane solution.'
_exptl_crystal_recrystallization_method
'Slow evapouration of a chloroform/hexane solution.'
_exptl_crystal_size_max          0.3187
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.0492
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0489P)^2^+0.4626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1884
_reflns_number_total             2105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cp06952a2.cif
_cod_data_source_block           ntnmpb
_cod_depositor_comments
'Adding full bibliography for 7229515--7229521.cif.'
_cod_original_cell_volume        1072.87(7)
_cod_database_code               7229519
_nottingham_internal_coll_name   NTNMPB
_nottingham_internal_coll_number 13957
_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, 4.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pcxnp7
_nottingham_internal_coll_date   09/09/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 10/09/2014
_nottingham_internal_process_user pcxnp7
_nottingham_internal_solution_date 10/09/2014
_nottingham_internal_solution_user pcxnp7
_nottingham_internal_refinement_date 5/11/2015
_nottingham_internal_refinement_user 'pcxnp7, pczcrp'
_nottingham_internal_self_validation_date 5/11/2015
_nottingham_internal_self_validation_user pczcrp
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C24 H26 N2 O2 S2'
_chemical_oxdiff_usercomment
'NTNMPB IN FOMBLIN FILM ON MICROMOUNT FOR NMP/NRC'
_reflns_odcompleteness_completeness 99.76
_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 Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C18(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C19(H19a,H19b,H19c)
;
_shelx_res_checksum              86991
_olex2_date_sample_data_collection 10/09/14
_olex2_date_sample_submission    05/09/14
_olex2_exptl_crystal_mounting_method 'In folmbiln film on micromount.'
_olex2_submission_original_sample_id NTNMPB
_olex2_submission_special_instructions 'No special instructions were received'