A cross-conjugation approach for high-performance diaryl-hemithioindigo photoswitches.
Zitzmann, Max; Hampel, Frank; Dube, Henry; Chemical science 14 (2023) 5734–5742; doi:10.1039/d2sc06939c

data_1568991
_publ_section_title
;
 A cross-conjugation approach for high-performance diaryl-hemithioindigo
 photoswitches.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              5734
_journal_page_last               5742
_journal_paper_doi               10.1039/d2sc06939c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C23 H12 N2 O S'
_chemical_formula_sum            'C23 H12 N2 O S'
_chemical_formula_weight         364.41
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-12-16 deposited with the CCDC.	2023-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.3090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1913(2)
_cell_length_b                   22.6255(3)
_cell_length_c                   13.0947(2)
_cell_measurement_reflns_used    7108
_cell_measurement_temperature    153.00(10)
_cell_measurement_theta_max      73.0140
_cell_measurement_theta_min      4.1270
_cell_volume                     3582.62(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      153.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2679
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -124.00 -96.00   1.00    1.00    --  -42.07 -99.00  60.00   28
  2  \w      6.00  70.00   1.00    1.00    --   42.07 -99.00 120.00   64
  3  \w     -4.00 116.00   1.00    1.00    --   42.07  19.00 -30.00  120
  4  \w     33.00 102.00   1.00    1.66    --  106.12 -61.00  60.00   69
  5  \w     81.00 123.00   1.00    1.66    --  106.12 -30.00   0.00   42
  6  \w     34.00  70.00   1.00    1.66    --  106.12 -30.00   0.00   36
  7  \w     85.00 174.00   1.00    1.66    --  106.12  61.00 -30.00   89
  8  \w     32.00 124.00   1.00    1.66    --  106.12 -45.00-180.00   92
  9  \w     78.00 160.00   1.00    1.66    --  106.12  30.00 -90.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1139093000
_diffrn_orient_matrix_UB_12      -0.0228099000
_diffrn_orient_matrix_UB_13      0.0213860000
_diffrn_orient_matrix_UB_21      0.0016217000
_diffrn_orient_matrix_UB_22      -0.0463891000
_diffrn_orient_matrix_UB_23      -0.0858882000
_diffrn_orient_matrix_UB_31      0.0570230000
_diffrn_orient_matrix_UB_32      -0.0443131000
_diffrn_orient_matrix_UB_33      0.0789831000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13496
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.191
_diffrn_reflns_theta_min         3.924
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.718
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_recrystallization_method
'The material was recrystallised from MeOH by slow evaporation'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.274
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00036(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0518P)^2^+2.4028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6064
_reflns_number_total             6961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06939c3.cif
_cod_data_source_block           21dub_mz04
_cod_depositor_comments
'Adding full bibliography for 1568986--1568991.cif.'
_cod_database_code               1568991
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H12 N3 O S'
_chemical_oxdiff_usercomment     MZ-214
_shelx_estimated_absorpt_t_max   0.650
_shelx_estimated_absorpt_t_min   0.539
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C25(H25),
 C26(H26), C32(H32), C33(H33), C35(H35), C36(H36), C14A(H14A), C15A(H15A),
 C16A(H16A), C17A(H17A), C22A(H22A), C23A(H23A), C25A(H25A), C26A(H26A),
 C32A(H32A), C33A(H33A), C35A(H35A), C36A(H36A)
;
_olex2_date_sample_data_collection 2009-06-05
_olex2_diffrn_ambient_temperature_device 'Cryojet - Oxford Instruments'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id MZ214
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.326
_oxdiff_exptl_absorpt_empirical_full_min 0.751