Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength
Benz, Sebastian; Mareda, Jiri; Besnard, Céline; Sakai, Naomi; Matile, Stefan; Chem. Sci.  (2017) –; doi:10.1039/C7SC03866F

data_1547682
_publ_section_title
;
 Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with
 high-precision selenium donors of variable strength
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC03866F
_journal_year                    2017
_chemical_formula_moiety         'C30 H26 N4 S2 Se2, C H Cl3'
_chemical_formula_sum            'C31 H27 Cl3 N4 S2 Se2'
_chemical_formula_weight         783.95
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-08-11 deposited with the CCDC.
2017-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.2300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9134(2)
_cell_length_b                   11.53190(10)
_cell_length_c                   18.2586(2)
_cell_measurement_reflns_used    31512
_cell_measurement_temperature    180
_cell_measurement_theta_max      74.2600
_cell_measurement_theta_min      3.8050
_cell_volume                     3353.78(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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      air
_diffrn_ambient_temperature      180
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -44.00  35.00   1.00    1.00    --  -41.08  77.00-180.00   79
  2  \w    -94.00 -68.00   1.00    1.00    --  -41.08 -38.00 -60.00   26
  3  \w   -114.00 -17.00   1.00    1.00    --  -41.08 -38.00  60.00   97
  4  \w     90.00 178.00   1.00    1.50    --  108.11  45.00 -90.00   88
  5  \w    139.00 165.00   1.00    1.50    --  108.11 125.00-180.00   26
  6  \w     76.00 178.00   1.00    1.50    --  108.11  15.00  30.00  102
  7  \w    123.00 159.00   1.00    1.50    --  108.11 125.00 120.00   36
  8  \w     37.00 124.00   1.00    1.50    --  108.11 -30.00 -30.00   87
  9  \w     50.00 112.00   1.00    1.50    --  108.11-125.00 150.00   62
 10  \w   -120.00 -94.00   1.00    1.00    --  -41.08 178.00  30.00   26
 11  \w    -50.00  15.00   1.00    1.00    --  -41.08 105.00  74.00   65
 12  \w   -117.00 -91.00   1.00    1.00    --  -41.08 -77.00  90.00   26
 13  \w   -112.00 -85.00   1.00    1.00    --  -41.08 -77.00 -30.00   27
 14  \w   -116.00  -9.00   1.00    1.00    --  -41.08 -77.00-180.00  107
 15  \w   -112.00  -8.00   1.00    1.00    --  -41.08 -77.00-120.00  104
 16  \w    -79.00  -8.00   1.00    1.00    --  -41.08 -77.00 -30.00   71
 17  \w    -77.00  -8.00   1.00    1.00    --  -41.08 -77.00  30.00   69
 18  \w    -40.00 -11.00   1.00    1.00    --  -41.08 -77.00  90.00   29
 19  \w      2.00  69.00   1.00    1.00    --   41.08 -99.00 -60.00   67
 20  \w      1.00  62.00   1.00    1.00    --   41.08 -99.00  30.00   61
 21  \w     25.00 109.00   1.00    1.50    --  108.11 -94.00 -30.00   84
 22  \w     79.00 105.00   1.00    1.50    --  108.11  61.00   0.00   26
 23  \w     76.00 101.00   1.00    1.50    --  108.11  77.00   0.00   25
 24  \w     79.00 146.00   1.00    1.50    --  108.11  61.00  90.00   67
 25  \w     36.00 109.00   1.00    1.50    --  108.11-125.00-180.00   73
 26  \w     79.00 163.00   1.00    1.50    --  108.11  61.00-180.00   84
 27  \w     79.00 105.00   1.00    1.50    --  108.11  61.00  60.00   26
 28  \w    117.00 143.00   1.00    1.50    --  108.11  77.00 120.00   26
 29  \w     80.00 153.00   1.00    1.50    --  108.11  59.00 160.52   73
 30  \w     79.00 105.00   1.00    1.50    --  108.11  61.00 -60.00   26
 31  \w     76.00 102.00   1.00    1.50    --  108.11  77.00-180.00   26
 32  \w     76.00 105.00   1.00    1.50    --  108.11  77.00 120.00   29
 33  \w    149.00 175.00   1.00    1.50    --  108.11  61.00  60.00   26
 34  \w     79.00 105.00   1.00    1.50    --  108.11  61.00 -90.00   26
 35  \w     79.00 131.00   1.00    1.50    --  108.11  61.00-120.00   52
 36  \w    138.00 169.00   1.00    1.50    --  108.11  77.00   0.00   31
 37  \w     79.00 105.00   1.00    1.50    --  108.11  61.00 120.00   26
 38  \w     76.00 120.00   1.00    1.50    --  108.11  77.00 -60.00   44
 39  \w    133.00 168.00   1.00    1.50    --  108.11  77.00 -60.00   35
 40  \w     76.00 101.00   1.00    1.50    --  108.11  77.00 -90.00   25
 41  \w     76.00 102.00   1.00    1.50    --  108.11  77.00  30.00   26
 42  \w     76.00 101.00   1.00    1.50    --  108.11  77.00 -30.00   25
 43  \w     76.00 122.00   1.00    1.50    --  108.11  77.00-150.00   46
 44  \w     79.00 105.00   1.00    1.50    --  108.11  61.00-150.00   26
 45  \w    121.00 177.00   1.00    1.50    --  108.11  77.00  30.00   56
 46  \w     76.00 177.00   1.00    1.50    --  108.11  77.00  90.00  101
 47  \w     76.00 102.00   1.00    1.50    --  108.11  77.00 150.00   26
 48  \w    145.00 175.00   1.00    1.50    --  108.11  77.00 150.00   30
 49  \w     93.00 119.00   1.00    1.50    --  108.11-125.00 -90.00   26
 50  \w     76.00 102.00   1.00    1.50    --  108.11  77.00-120.00   26
 51  \w     79.00 153.00   1.00    1.50    --  108.11  61.00 150.00   74
 52  \w     79.00 114.00   1.00    1.50    --  108.11  61.00 -30.00   35
 53  \w     79.00 105.00   1.00    1.50    --  108.11  61.00  30.00   26
 54  \w     76.00 105.00   1.00    1.50    --  108.11  77.00  60.00   29
 55  \w     32.00 136.00   1.00    1.50    --  108.11 -77.00-180.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0761535000
_diffrn_orient_matrix_UB_12      -0.0264035000
_diffrn_orient_matrix_UB_13      -0.0834418000
_diffrn_orient_matrix_UB_21      0.0595591000
_diffrn_orient_matrix_UB_22      -0.0282979000
_diffrn_orient_matrix_UB_23      -0.0373038000
_diffrn_orient_matrix_UB_31      0.0026162000
_diffrn_orient_matrix_UB_32      -0.1278629000
_diffrn_orient_matrix_UB_33      0.0255153000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            55832
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.290
_diffrn_reflns_theta_min         4.703
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.340
_exptl_absorpt_correction_T_max  0.672
_exptl_absorpt_correction_T_min  0.431
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.077
_refine_diff_density_max         1.035
_refine_diff_density_min         -1.171
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         6780
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0664P)^2^+4.2380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1146
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6254
_reflns_number_total             6780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03866f2.cif
_cod_data_source_block           sb420_2
_cod_database_code               1547682
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C31 H27 Cl3 N4 S2 Se2'
_reflns_odcompleteness_completeness 99.97
_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. Uiso/Uaniso restraints and constraints
Uanis(C2) = Uanis(C1)
3. Rigid body (RIGU) restrains
 Cl1, Cl3, Cl2, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl4, Cl6, Cl5, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Cl1)=Sof(Cl3)=Sof(Cl2)=Sof(C1)=Sof(H1)=1-FVAR(1)
 Sof(Cl4)=Sof(Cl6)=Sof(Cl5)=Sof(C2)=Sof(H2)=FVAR(1)
5.a Free rotating group:
 Cl1(Cl3,Cl2,C1), Cl4(Cl6,Cl5,C2)
5.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C30(H30), C31(H31), C33(H33), C34(H34)
5.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
;
_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.762