The effect of thionation of the carbonyl group on the photophysics of compact spiro rhodamine-naphthalimide electron donor-acceptor dyads: intersystem crossing, charge separation, and electron spin dynamics.
Xiao, Xiao; Mu, Tong; Sukhanov, Andrey A.; Zhou, Yihang; Yu, Peiran; Yu, Fabiao; Elmali, Ayhan; Zhao, Jianzhang; Karatay, Ahmet; Voronkova, Violeta K.; Physical chemistry chemical physics : PCCP 25 (2023) 31667–31682; doi:10.1039/d3cp04891h

data_7247673
_publ_section_title
;
 The effect of thionation of the carbonyl group on the photophysics of
 compact spiro rhodamine-naphthalimide electron donor-acceptor dyads:
 intersystem crossing, charge separation, and electron spin dynamics.
;
_journal_issue                   46
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              31667
_journal_page_last               31682
_journal_paper_doi               10.1039/d3cp04891h
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C18 H18 N2 O S2'
_chemical_formula_sum            'C18 H18 N2 O S2'
_chemical_formula_weight         342.46
_chemical_name_systematic        NIS-NHAc
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2023-09-11 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                76.969(2)
_cell_angle_beta                 75.0350(10)
_cell_angle_gamma                72.6480(10)
_cell_formula_units_Z            4
_cell_length_a                   9.2114(4)
_cell_length_b                   13.4808(6)
_cell_length_c                   14.5200(7)
_cell_measurement_reflns_used    5255
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.54
_cell_measurement_theta_min      2.94
_cell_volume                     1640.93(13)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26161
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.344
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6885
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1168 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.9237.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0585P)^2^+1.9559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1465
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4116
_reflns_number_total             5766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cp04891h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7247673--7247674.cif.'
_cod_database_code               7247673
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C011(H01A,H01B), C013(H01C,H01D), C015(H01H,H01I), C016(H01P,H01Q), C017(H01R,
 H01S), C01A(H01W,H01X)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), N009(H009), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y)
2.c Idealised Me refined as rotating group:
 C010(H01M,H01N,H01O), C014(H01E,H01F,H01G), C018(H01J,H01K,H01L), C019(H01T,
 H01U,H01V)
;
_olex2_submission_special_instructions 'No special instructions were received'