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_7229517
_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 O3 S'
_chemical_formula_sum            'C24 H26 N2 O3 S'
_chemical_formula_weight         422.53
_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                 100.773(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1049(7)
_cell_length_b                   8.6592(7)
_cell_length_c                   13.7163(8)
_cell_measurement_reflns_used    1458
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.4970
_cell_measurement_theta_min      6.0520
_cell_volume                     1062.35(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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 10.6296
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
  1 omega  -49.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -60.0000 50

  2 omega  -50.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000 -120.0000 75

  3 omega -115.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000 -120.0000 108

  4 omega   34.00   73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   90.0000 39

  5 omega   44.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -61.0000  -30.0000 77

  6 omega   70.00   96.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000 -120.0000 26

  7 omega   36.00   94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000 -150.0000 58

  8 omega   38.00   79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000  -90.0000 41

  9 omega   29.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000 -150.0000 80

 10 omega   93.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000    0.0000 81
;
_diffrn_measurement_device       '\k geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      0.1452148000
_diffrn_orient_matrix_UB_12      0.0760352000
_diffrn_orient_matrix_UB_13      -0.0185095000
_diffrn_orient_matrix_UB_21      -0.0905911000
_diffrn_orient_matrix_UB_22      0.1389223000
_diffrn_orient_matrix_UB_23      -0.0489523000
_diffrn_orient_matrix_UB_31      0.0188751000
_diffrn_orient_matrix_UB_32      0.0810338000
_diffrn_orient_matrix_UB_33      0.1016745000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3983
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.084
_diffrn_reflns_theta_min         4.944
_diffrn_source                   'microfocus x-ray tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    1.582
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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 light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       irregular
_exptl_crystal_F_000             448
_exptl_crystal_preparation
;
'Synthesised by reaction of N,N'-(1-ethylpropyl)naphthalene-1,4,5,8-tetracarboxylic 
diimide with Lawesson's reagent in anhydrous toluene.'
;
_exptl_crystal_recrystallization_method 'Evapouration of acetonitrile.'
_exptl_crystal_size_max          0.4234
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.1446
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0715
_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^)+(0.1392P)^2^+0.2227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2188
_refine_ls_wR_factor_ref         0.2373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1582
_reflns_number_total             2080
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cp06952a2.cif
_cod_data_source_block           ntnmpc
_cod_depositor_comments
'Adding full bibliography for 7229515--7229521.cif.'
_cod_original_cell_volume        1062.35(13)
_cod_database_code               7229517
_nottingham_internal_coll_name   NTNMPC
_nottingham_internal_coll_number 13971
_nottingham_internal_coll_client NP/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   17/11/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 17/11/2014
_nottingham_internal_process_user pcxnp7
_nottingham_internal_solution_date 17/11/2014
_nottingham_internal_solution_user pcxnp7
_nottingham_internal_refinement_date 5/11/2015
_nottingham_internal_refinement_user pcxnp7,
_nottingham_internal_self_archive_date 5/11/2015
_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 O3 S1'
_chemical_oxdiff_usercomment
'NTNMPC1 IN FOMBLIN FILM ON MICROMOUNT FOR NMP/NRC GVB352'
_reflns_odcompleteness_completeness 99.51
_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. Others
 Fixed Sof: O11(0.75) S11A(0.25) O14A(0.75) S14(0.25)
3.a Ternary CH refined with riding coordinates:
 C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              97120
_olex2_date_sample_data_collection 17/11/14
_olex2_date_sample_submission    14/11/14
_olex2_exptl_crystal_mounting_method 'In fomblin film on micromount.'
_olex2_submission_original_sample_id NTNMPC1
_olex2_submission_special_instructions 'No special instructions were received'