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_1568986
_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         'C25 H24 N2 O S'
_chemical_formula_sum            'C25 H24 N2 O S'
_chemical_formula_weight         400.52
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-09
_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                 100.735(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9704(8)
_cell_length_b                   21.4506(10)
_cell_length_c                   9.7628(5)
_cell_measurement_reflns_used    2121
_cell_measurement_temperature    152.95(10)
_cell_measurement_theta_max      68.5360
_cell_measurement_theta_min      4.4940
_cell_volume                     2051.4(2)
_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      152.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.957
_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   -114.00 -38.00   1.00   15.27    --  -42.06 -38.00-120.00   76
  2  \w   -108.00 -18.00   1.00   15.27    --  -42.06 -38.00 -60.00   90
  3  \w     72.00 159.00   1.00   61.09    --   98.29  61.00-120.00   87
  4  \w    104.00 172.00   1.00   61.09    --   98.29 125.00  90.00   68
  5  \w     33.00 126.00   1.00   61.09    --   98.29 -61.00  90.00   93
  6  \w     31.00 119.00   1.00   61.09    --   98.29 -61.00 -30.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1189519000
_diffrn_orient_matrix_UB_12      -0.0260588000
_diffrn_orient_matrix_UB_13      0.0636203000
_diffrn_orient_matrix_UB_21      -0.0999534000
_diffrn_orient_matrix_UB_22      0.0149301000
_diffrn_orient_matrix_UB_23      -0.1363201000
_diffrn_orient_matrix_UB_31      0.0244007000
_diffrn_orient_matrix_UB_32      -0.0651852000
_diffrn_orient_matrix_UB_33      -0.0564462000
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6287
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.260
_diffrn_reflns_theta_min         4.514
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.537
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.807
_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 reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of MeOH and i-Hexane  by solvent layering'
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0677
_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^)+(0.0951P)^2^+2.2824P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.1891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3060
_reflns_number_total             3658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06939c3.cif
_cod_data_source_block           21dub_mz08_2
_cod_depositor_comments
'Adding full bibliography for 1568986--1568991.cif.'
_cod_database_code               1568986
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H24 N2 O S'
_chemical_oxdiff_usercomment     MZ-198
_reflns_odcompleteness_completeness 98.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,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)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C)
;
_olex2_date_sample_data_collection 2021-09-07
_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 MZ198
_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 1.271
_oxdiff_exptl_absorpt_empirical_full_min 0.854