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_1557640
_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_absolute_configuration unk
_chemical_formula_moiety         'C30 H27 Br O3 S2'
_chemical_formula_sum            'C30 H27 Br O3 S2'
_chemical_formula_weight         579.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-06
_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                90
_cell_angle_beta                 102.2150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   23.8898(2)
_cell_length_b                   6.76170(10)
_cell_length_c                   24.8099(2)
_cell_measurement_reflns_used    52225
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2620
_cell_measurement_theta_min      3.7580
_cell_volume                     3916.95(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -32.00  22.00   1.00    1.00    --    0.00  82.00 150.00   54
  2  \w    -68.00 -33.00   1.00    1.00    --    0.00 -19.00-180.00   35
  3  \w     -7.00  18.00   1.00    1.00    --    0.00 -38.00 150.00   25
  4  \w    -88.00 -56.00   1.00    1.00    --    0.00 -57.00 -60.00   32
  5  \w    -19.00  88.00   1.00    1.00    --    0.00  38.00  60.00  107
  6  \w     37.00  88.00   1.00    1.00    --    0.00  82.00 150.00   51
  7  \w      1.00  88.00   1.00    1.00    --    0.00  38.00-180.00   87
  8  \w    -87.00 -22.00   1.00    1.00    --    0.00 -38.00 150.00   65
  9  \w     -3.00  24.00   1.00    1.00    --    0.00 -19.00-180.00   27
 10  \w    -29.00  17.00   1.00    1.00    --    0.00 -57.00 -60.00   46
 11  \w    -32.00  84.00   1.00    1.00    --    0.00  82.00 -60.00  116
 12  \w     59.00  87.00   1.00    1.00    --    0.00  57.00   0.00   28
 13  \w    -22.00  29.00   1.00    1.00    --    0.00  57.00   0.00   51
 14  \w    129.00 185.00   1.00    1.00    --   95.80  74.00  17.31   56
 15  \w     66.00  92.00   1.00    1.00    --   95.80  74.00  17.31   26
 16  \w     71.00  96.00   1.00    1.00    --   95.80  60.00-161.05   25
 17  \w     69.00 185.00   1.00    1.00    --   95.80  67.00  33.12  116
 18  \w     65.00 181.00   1.00    1.00    --   95.80  77.00 -45.32  116
 19  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  -3.51   25
 20  \w     71.00 127.00   1.00    1.00    --   95.80  61.00 167.44   56
 21  \w     71.00 185.00   1.00    1.00    --   95.80  61.00 150.00  114
 22  \w     32.00 128.00   1.00    1.00    --   95.80 -82.00   0.00   96
 23  \w     21.00 127.00   1.00    1.00    --   95.80 -82.00-150.00  106
 24  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 25  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 26  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 27  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 28  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 29  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 30  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 31  \w     70.00 110.00   1.00    1.00    --   95.80  64.00 -52.05   40
 32  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 33  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 34  \w     71.00 184.00   1.00    1.00    --   95.80  61.00  68.49  113
 35  \w    157.00 183.00   1.00    1.00    --   95.80  77.00  83.39   26
 36  \w     99.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   86
 37  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 38  \w     64.00  90.00   1.00    1.00    --   95.80  79.00 107.76   26
 39  \w     65.00  92.00   1.00    1.00    --   95.80  77.00 120.00   27
 40  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 41  \w    135.00 183.00   1.00    1.00    --   95.80  80.00 -78.49   48
 42  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 43  \w     75.00 137.00   1.00    1.00    --   95.80  45.00  30.00   62
 44  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 45  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 46  \w     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 47  \w    151.00 176.00   1.00    1.00    --   95.80  82.00   0.00   25
 48  \w     71.00 183.00   1.00    1.00    --   95.80  61.00  90.00  112
 49  \w     66.00  91.00   1.00    1.00    --   95.80  74.00 -96.87   25
 50  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 51  \w     65.00 146.00   1.00    1.00    --   95.80  77.00 -30.00   81
 52  \w     76.00 175.00   1.00    1.00    --   95.80  45.00-150.00   99
 53  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 54  \w     71.00  97.00   1.00    1.00    --   95.80  61.00-120.00   26
 55  \w     64.00  90.00   1.00    1.00    --   95.80  80.00 -78.49   26
 56  \w     54.00 119.00   1.00    1.00    --   95.80 -82.00  90.00   65
 57  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 58  \w      6.00 120.00   1.00    1.00    --   95.80 -61.00   0.00  114
 59  \w     65.00 178.00   1.00    1.00    --   95.80  76.00 107.21  113
 60  \w    142.00 168.00   1.00    1.00    --   95.80  60.00-161.05   26
 61  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  83.39   25
 62  \w     73.00 185.00   1.00    1.00    --   95.80  53.00 -97.19  112
 63  \w     73.00  99.00   1.00    1.00    --   95.80  61.00-150.00   26
 64  \w     53.00 112.00   1.00    1.00    --   95.80 -82.00 -90.00   59
 65  \w     75.00 178.00   1.00    1.00    --   95.80  45.00-116.77  103
;
_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      -0.0028465000
_diffrn_orient_matrix_UB_12      0.0494494000
_diffrn_orient_matrix_UB_13      -0.0611253000
_diffrn_orient_matrix_UB_21      0.0654589000
_diffrn_orient_matrix_UB_22      -0.0243399000
_diffrn_orient_matrix_UB_23      0.0091523000
_diffrn_orient_matrix_UB_31      -0.0078358000
_diffrn_orient_matrix_UB_32      -0.2210669000
_diffrn_orient_matrix_UB_33      -0.0147014000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            96928
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.646
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27724
_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    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             1788
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.534
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 5406 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     973
_refine_ls_number_reflns         13531
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0370
_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^+1.9138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                13005
_reflns_number_total             13531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01060j2.cif
_cod_data_source_block           exp_1142
_cod_depositor_comments
;Adding full bibliography for 1557638--1557640.cif.

 Adding full bibliography for 1557638--1557640.cif.
;
_cod_database_code               1557640
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.95
_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
2.a Ternary CH refined with riding coordinates:
 C23(H23), C25(H25), C27(H27), C53(H53), C55(H55), C57(H57), C83(H83),
 C86(H86), C88(H88)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C22(H22A,H22B), C24(H24A,H24B), C26(H26A,H26B), C28(H28A,
 H28B), C29(H29A,H29B), C30(H30A,H30B), C47(H47A,H47B), C52(H52A,H52B),
 C54(H54A,H54B), C56(H56A,H56B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B),
  C77(H77A,H77B), C82(H82A,H82B), C84(H84A,H84B), C85(H85A,H85B), C87(H87A,
 H87B), C89(H89A,H89B), C90(H90A,H90B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C12(H12), C14(H14),
 C15(H15), C32(H32), C33(H33), C34(H34), C35(H35), C37(H37), C39(H39), C40(H40),
  C42(H42), C43(H43), C45(H45), C62(H62), C63(H63), C64(H64), C65(H65),
 C67(H67), C69(H69), C70(H70), C72(H72), C73(H73), C75(H75)
;
_shelx_res_checksum              12847
_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 2.880
_oxdiff_exptl_absorpt_empirical_full_min 0.582