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_7229520
_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 O4'
_chemical_formula_sum            'C24 H26 N2 O4'
_chemical_formula_weight         406.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.022(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4100(3)
_cell_length_b                   8.3348(2)
_cell_length_c                   18.3351(4)
_cell_measurement_reflns_used    3554
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.8280
_cell_measurement_theta_min      4.9110
_cell_volume                     2011.51(8)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
  1 omega  -48.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  -30.0000 68

  2 omega -110.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -77.0000    0.0000 100

  3 omega -100.00  -59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000 -148.0000  -11.0000 41

  4 omega   38.00   97.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000 -120.0000 59

  5 omega   48.00   94.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000 -180.0000 46

  6 omega   32.00  174.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000    0.0000 -180.0000 142

  7 omega   31.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   30.0000 60

  8 omega   62.00   87.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000  120.0000 25

  9 omega   34.00   59.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   90.0000 25

 10 omega   35.00   92.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  -30.0000 57
;
_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      -0.0477330000
_diffrn_orient_matrix_UB_12      -0.0088001000
_diffrn_orient_matrix_UB_13      -0.0832337000
_diffrn_orient_matrix_UB_21      0.0876292000
_diffrn_orient_matrix_UB_22      0.1022264000
_diffrn_orient_matrix_UB_23      -0.0183307000
_diffrn_orient_matrix_UB_31      0.0611104000
_diffrn_orient_matrix_UB_32      -0.1538980000
_diffrn_orient_matrix_UB_33      -0.0074745000
_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  0.0157
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7787
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.399
_diffrn_reflns_theta_min         3.762
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.881
_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 pinkish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   pinkish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_preparation
'Synthesised from naphthalene-1,4,5,8-tetracarboxylic dianhydride and 3-aminopentane in DMF.'
_exptl_crystal_recrystallization_method
'Evapouration of a chloroform solution of compound.'
_exptl_crystal_size_max          0.2461
_exptl_crystal_size_mid          0.2271
_exptl_crystal_size_min          0.1064
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0608P)^2^+0.3190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3321
_reflns_number_total             3963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cp06952a2.cif
_cod_data_source_block           ntnmpd
_cod_depositor_comments
'Adding full bibliography for 7229515--7229521.cif.'
_cod_original_cell_volume        2011.50(9)
_cod_database_code               7229520
_nottingham_internal_coll_name   NTNMPD
_nottingham_internal_coll_number 13974
_nottingham_internal_coll_client NMP/NRC
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '2.0000, 8.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pcxnp7
_nottingham_internal_coll_date   15/09/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 15/09/2014
_nottingham_internal_process_user pcxnp7
_nottingham_internal_solution_date 15/09/2014
_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 pczwl
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C24 H26 N2 O4'
_chemical_oxdiff_usercomment
'NTNMPDB IN FOMBLIN FILM ON MICROMOUNT FOR NMP/NRC'
_reflns_odcompleteness_completeness 99.84
_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:
 C21(H21), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22a,H22b), C24(H24a,H24b), C27(H27a,H27b), C29(H29a,H29b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C25(H25a,H25b,H25c), C28(H28a,H28b,H28c), C30(H30a,H30b,
 H30c)
;
_shelx_res_checksum              64792
_olex2_date_sample_data_collection 15/09/14
_olex2_date_sample_submission    11/09/14
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id NTNMPD
_olex2_submission_special_instructions 'No special instructions were received'