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_7229516
_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         'C40 H33 N3 O4 S, C H Cl3'
_chemical_formula_sum            'C41 H34 Cl3 N3 O4 S'
_chemical_formula_weight         771.12
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-08-25 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                87.754(3)
_cell_angle_beta                 87.804(3)
_cell_angle_gamma                78.925(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7193(3)
_cell_length_b                   11.6007(4)
_cell_length_c                   18.7861(9)
_cell_measurement_reflns_used    5449
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.1810
_cell_measurement_theta_min      4.0300
_cell_volume                     1862.47(13)
_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    'ShelXS (Sheldrick, 2008)'
_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 10.3613
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
  1 omega -112.00  -13.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -77.0000 -150.0000 99

  2 omega  -53.00   32.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -30.0000 85

  3 omega   26.00   70.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3152  -57.0000  -30.0000 44

  4 omega   22.00   86.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3152   57.0000  120.0000 64

  5 omega   42.00   77.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3152  -99.0000 -150.0000 35

  6 omega   56.00   89.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -30.0000  -90.0000 33

  7 omega   34.00   60.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -95.0000 -120.0000 26

  8 omega   58.00  137.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -77.0000  150.0000 79

  9 omega   73.00  121.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087 -125.0000  150.0000 48

 10 omega   49.00  102.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -95.0000   30.0000 53

 11 omega   35.00   98.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -45.0000    0.0000 63

 12 omega   83.00  109.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -95.0000 -120.0000 26

 13 omega   35.00   86.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -45.0000  120.0000 51

 14 omega   98.00  178.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087   30.0000  120.0000 80

 15 omega   57.00   82.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -30.0000  -60.0000 25

 16 omega   31.00   91.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -30.0000 -150.0000 60

 17 omega   67.00  171.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087   15.0000 -120.0000 104

 18 omega   49.00   98.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -45.0000   60.0000 49

 19 omega   37.00  104.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8087  -95.0000  -30.0000 67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      0.0270408000
_diffrn_orient_matrix_UB_12      -0.0553134000
_diffrn_orient_matrix_UB_13      -0.0737476000
_diffrn_orient_matrix_UB_21      0.1075856000
_diffrn_orient_matrix_UB_22      -0.1081735000
_diffrn_orient_matrix_UB_23      0.0331291000
_diffrn_orient_matrix_UB_31      -0.1419135000
_diffrn_orient_matrix_UB_32      -0.0597447000
_diffrn_orient_matrix_UB_33      0.0143360000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13098
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.089
_diffrn_reflns_theta_min         4.610
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.128
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   gaussian
_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)
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 blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.6111
_exptl_crystal_size_mid          0.3456
_exptl_crystal_size_min          0.0741
_refine_diff_density_max         2.203
_refine_diff_density_min         -1.197
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.409
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         7319
_refine_ls_number_restraints     362
_refine_ls_restrained_S_all      1.436
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.1021
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3062
_refine_ls_wR_factor_ref         0.3289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6114
_reflns_number_total             7319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cp06952a2.cif
_cod_data_source_block           ntnmpg
_cod_depositor_comments
'Adding full bibliography for 7229515--7229521.cif.'
_cod_original_cell_volume        1862.48(13)
_cod_database_code               7229516
_nottingham_internal_coll_name   NTNMPG
_nottingham_internal_coll_number 14524
_nottingham_internal_coll_client NMP/NRC
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '26.0000, 104.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pcxnp
_nottingham_internal_coll_date   10/03/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_date 12/03/2015
_nottingham_internal_process_user pcxnp7
_nottingham_internal_solution_date 5/11/2015
_nottingham_internal_solution_user pcxnp/pczcrp/pczwl
_nottingham_internal_refinement_date 5/11/2015
_nottingham_internal_refinement_user pczcrp/pczwl
_nottingham_internal_self_archive_date 06/11/2015
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C40 H33 N3 O4 S1'
_chemical_oxdiff_usercomment
'#14524 NTNMPG IN FOMBLIN FILM ON MICROMOUNT FOR NMP/NRC SN-460'
_reflns_odcompleteness_completeness 99.70
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C43-C42 \\sim C42A-C43A
 with sigma of 0.02
 C44-C43 \\sim C44A-C43A
 with sigma of 0.02
 C44-C45 \\sim C45A-C44A
 with sigma of 0.02
 C46-C45 \\sim C46A-C45A
 with sigma of 0.02
 C47-C46 \\sim C46A-C47A
 with sigma of 0.02
 C47A-C48A \\sim C48-C47
 with sigma of 0.02
 C1A-Cl1A \\sim C1A-Cl2A \\sim C1A-Cl3A \\sim C1B-Cl1B \\sim C1B-Cl2B \\sim
C1B-Cl3B
 with sigma of 0.02
 Cl1A-Cl2A \\sim Cl2A-Cl3A \\sim Cl3A-Cl1A \\sim Cl1B-Cl2B \\sim Cl2B-Cl3B
\\sim Cl3B-Cl1B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C41 \\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim
C42A \\sim C43A \\sim C44A \\sim C45A \\sim C46A \\sim C47A \\sim C48A \\sim
C1A \\sim Cl1A \\sim Cl2A \\sim Cl3A \\sim C1B \\sim Cl2B \\sim Cl3B \\sim
Cl1B: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C42, C43, C44, C45, C46, C47, C48, C42A, C43A, C44A, C45A, C46A, C47A, C48A,
 C1A, Cl1A, Cl2A, Cl3A, C1B, Cl2B, Cl3B, Cl1B, C41
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C42, C43, C44, C45, C46, C47, C48} sigma for 1-2: 0.02, 1-3: 0.04
as
{C42A, C43A, C44A, C45A, C46A, C47A, C48A}
6. Others
 Sof(H41C)=Sof(H41D)=Sof(C42A)=Sof(H42C)=Sof(H42D)=Sof(C43A)=Sof(H43C)=
 Sof(H43D)=Sof(C44A)=Sof(H44C)=Sof(H44D)=Sof(C45A)=Sof(H45C)=Sof(H45D)=
 Sof(C46A)=Sof(H46C)=Sof(H46D)=Sof(C47A)=Sof(H47C)=Sof(H47D)=Sof(C48A)=
 Sof(H48D)=Sof(H48E)=Sof(H48F)=Sof(C1B)=Sof(H1B)=Sof(Cl2B)=Sof(Cl3B)=Sof(Cl1B)=
 1-FVAR(1)
 Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=
 Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(C46)=Sof(H46A)=
 Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=
 Sof(C1A)=Sof(H1A)=Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B)
7.b Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C41(H41C,H41D), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,
 H44B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C42A(H42C,H42D),
 C43A(H43C,H43D), C44A(H44C,H44D), C45A(H45C,H45D), C46A(H46C,H46D), C47A(H47C,
 H47D)
7.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C22(H22), C23(H23), C25(H25), C26(H26),
 C29(H29), C30(H30), C31(H31), C32(H32), C36(H36), C37(H37), C38(H38), C39(H39)
7.d Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C48A(H48D,H48E,H48F)
;
_shelx_res_checksum              34688
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'