Steric and stereoscopic disulfide construction for cross-linkage via N-dithiophthalimides
Gao, Wen-Chao; Tian, Jun; Shang, Yu-Zhu; Jiang, Xuefeng; Chemical Science 11 (2020) 3903–3908; doi:10.1039/D0SC01060J

data_1557639
_publ_section_title
;
 Steric and stereoscopic disulfide construction for cross-linkage via
 N-dithiophthalimides
;
_journal_issue                   15
_journal_name_full               'Chemical Science'
_journal_page_first              3903
_journal_page_last               3908
_journal_paper_doi               10.1039/D0SC01060J
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C18 H15 O3 S2'
_chemical_formula_sum            'C18 H15 O3 S2'
_chemical_formula_weight         343.42
_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     dual
_audit_creation_date             2019-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-07 deposited with the CCDC.	2020-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                99.463(2)
_cell_angle_beta                 113.869(3)
_cell_angle_gamma                105.929(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2340(3)
_cell_length_b                   9.7230(3)
_cell_length_c                   10.6174(3)
_cell_measurement_reflns_used    12649
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0410
_cell_measurement_theta_min      4.7740
_cell_volume                     796.06(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.964
_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    -88.00 -51.00   1.00    1.00    --    0.00 -38.00 120.00   37
  2  \w    -28.00  24.00   1.00    1.00    --    0.00 -19.00-120.00   52
  3  \w    -23.00  12.00   1.00    1.00    --    0.00  57.00   0.00   35
  4  \w     13.00  44.00   1.00    1.00    --    0.00  77.00 120.00   31
  5  \w     48.00  88.00   1.00    1.00    --    0.00  77.00  30.00   40
  6  \w    -20.00  36.00   1.00    1.00    --    0.00  57.00 -30.00   56
  7  \w    -62.00 -32.00   1.00    1.00    --    0.00 -19.00-120.00   30
  8  \w    -22.00  19.00   1.00    1.00    --    0.00  57.00-150.00   41
  9  \w     49.00  88.00   1.00    1.00    --    0.00  57.00 -30.00   39
 10  \w    -12.00  19.00   1.00    1.00    --    0.00 -38.00 120.00   31
 11  \w    -31.00  -2.00   1.00    1.00    --    0.00 -57.00 -60.00   29
 12  \w    -30.00  22.00   1.00    1.00    --    0.00  77.00  30.00   52
 13  \w     35.00  85.00   1.00    1.00    --    0.00  57.00   0.00   50
 14  \w     33.00  88.00   1.00    1.00    --    0.00  57.00-150.00   55
 15  \w    -27.00   0.00   1.00    1.00    --    0.00  77.00 120.00   27
 16  \w     65.00  97.00   1.00    1.00    --   95.80  77.00 -60.00   32
 17  \w     58.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00   70
 18  \w    119.00 185.00   1.00    1.00    --   95.80  45.00 150.00   66
 19  \w    127.00 185.00   1.00    1.00    --   95.80  77.00   0.00   58
 20  \w     66.00  92.00   1.00    1.00    --   95.80  77.00   0.00   26
 21  \w     76.00 109.00   1.00    1.00    --   95.80  45.00 150.00   33
 22  \w     69.00 184.00   1.00    1.00    --   95.80  65.00-140.62  115
 23  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 24  \w    103.00 129.00   1.00    1.00    --   95.80  77.00  30.00   26
 25  \w     63.00  99.00   1.00    1.00    --   95.80  82.00 120.00   36
 26  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 27  \w     12.00  38.00   1.00    1.00    --   95.80 -61.00-180.00   26
 28  \w     67.00 118.00   1.00    1.00    --   95.80 -61.00-180.00   51
 29  \w     77.00 159.00   1.00    1.00    --   95.80  45.00 -60.00   82
 30  \w     71.00  97.00   1.00    1.00    --   95.80  61.00  60.00   26
 31  \w    109.00 184.00   1.00    1.00    --   95.80  82.00-180.00   75
 32  \w     71.00 105.00   1.00    1.00    --   95.80  61.00  30.00   34
 33  \w     64.00  89.00   1.00    1.00    --   95.80  82.00-180.00   25
 34  \w    159.00 185.00   1.00    1.00    --   95.80  77.00  60.00   26
 35  \w    119.00 184.00   1.00    1.00    --   95.80  82.00  90.00   65
 36  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 37  \w    114.00 183.00   1.00    1.00    --   95.80  82.00 -90.00   69
 38  \w     64.00  90.00   1.00    1.00    --   95.80  82.00  90.00   26
 39  \w    127.00 185.00   1.00    1.00    --   95.80  61.00 -30.00   58
 40  \w     76.00 102.00   1.00    1.00    --   95.80  61.00   0.00   26
 41  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 42  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 -30.00   26
 43  \w    124.00 161.00   1.00    1.00    --   95.80  77.00-120.00   37
 44  \w     63.00  98.00   1.00    1.00    --   95.80  82.00-120.00   35
 45  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 -90.00   26
 46  \w     51.00 126.00   1.00    1.00    --   95.80 -82.00  30.00   75
 47  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 48  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 49  \w     47.00 123.00   1.00    1.00    --   95.80 -82.00-150.00   76
 50  \w    150.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   35
 51  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 120.00   26
 52  \w    154.00 179.00   1.00    1.00    --   95.80  61.00 120.00   25
 53  \w     65.00  94.00   1.00    1.00    --   95.80  77.00-180.00   29
 54  \w     80.00 151.00   1.00    1.00    --   95.80  45.00   0.00   71
 55  \w     76.00 156.00   1.00    1.00    --   95.80  45.00  90.00   80
 56  \w     75.00 102.00   1.00    1.00    --   95.80  45.00 120.00   27
 57  \w    119.00 183.00   1.00    1.00    --   95.80  61.00  60.00   64
 58  \w     76.00 105.00   1.00    1.00    --   95.80  45.00-180.00   29
 59  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 60  \w     51.00  77.00   1.00    1.00    --   95.80 -77.00  90.00   26
 61  \w     89.00 115.00   1.00    1.00    --   95.80 -77.00  90.00   26
 62  \w     68.00  93.00   1.00    1.00    --   95.80  82.00 -60.00   25
 63  \w     64.00  99.00   1.00    1.00    --   95.80  82.00 -90.00   35
 64  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 65  \w    139.00 171.00   1.00    1.00    --   95.80  38.00-152.35   32
 66  \w     76.00 112.00   1.00    1.00    --   95.80  38.00-152.35   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1780703000
_diffrn_orient_matrix_UB_12      -0.0253908000
_diffrn_orient_matrix_UB_13      -0.0123982000
_diffrn_orient_matrix_UB_21      0.0778394000
_diffrn_orient_matrix_UB_22      0.0377691000
_diffrn_orient_matrix_UB_23      0.1659467000
_diffrn_orient_matrix_UB_31      0.0326283000
_diffrn_orient_matrix_UB_32      0.1674292000
_diffrn_orient_matrix_UB_33      0.0149213000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15559
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.516
_diffrn_reflns_theta_min         4.796
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       block
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.6090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3063
_reflns_number_total             3149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01060j2.cif
_cod_data_source_block           exp_821
_cod_depositor_comments
;Adding full bibliography for 1557638--1557640.cif.

 Adding full bibliography for 1557638--1557640.cif.
;
_cod_database_code               1557639
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              25267
_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 3.208
_oxdiff_exptl_absorpt_empirical_full_min 0.410