Reactions of N-heterocyclic carbene-based chalcogenoureas with halogens: a diverse range of outcomes
Saab, Marina; Nelson, David J.; Leech, Matthew C.; Lam, Kevin; Nolan, Steven P.; Nahra, Fady; Van Hecke, Kristof; Dalton Transactions  (2022) –; doi:10.1039/D2DT00010E

data_7709503
_publ_section_title
;
 Reactions of N-heterocyclic carbene-based chalcogenoureas with halogens:
 a diverse range of outcomes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT00010E
_journal_year                    2022
_chemical_formula_moiety         'C21 H24 Br2 N2 S'
_chemical_formula_sum            'C21 H24 Br2 N2 S'
_chemical_formula_weight         496.28
_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             2020-09-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.698(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3863(2)
_cell_length_b                   15.2158(2)
_cell_length_c                   14.1625(3)
_cell_measurement_reflns_used    8868
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.8220
_cell_measurement_theta_min      4.3300
_cell_volume                     2154.70(7)
_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 (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      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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   -122.00  -1.00   1.00    1.00    --  -41.55 -19.00  30.00  121
  2  \w    -87.00  -6.00   1.00    1.00    --  -41.55 125.00 120.00   81
  3  \w     27.00  98.00   1.00    1.00    --   41.55-125.00 -60.00   71
  4  \w     80.00 178.00   1.00    1.00    --  106.01  45.00 150.00   98
  5  \w     34.00 135.00   1.00    1.00    --  106.01 -61.00   0.00  101
  6  \w    103.00 178.00   1.00    1.00    --  106.01  77.00  60.00   75
  7  \w     97.00 178.00   1.00    1.00    --  106.01 125.00   0.00   81
  8  \w     33.00 112.00   1.00    1.00    --  106.01-125.00 -60.00   79
  9  \w     33.00 112.00   1.00    1.00    --  106.01-125.00-150.00   79
 10  \w     23.00 107.00   1.00    1.00    --  106.01 -94.00 -30.00   84
 11  \w   -114.00 -13.00   1.00    1.00    --  -41.55 -57.00 -30.00  101
 12  \w   -114.00 -13.00   1.00    1.00    --  -41.55 -57.00-120.00  101
 13  \w     13.00 114.00   1.00    1.00    --   41.55  57.00-180.00  101
 14  \w     80.00 178.00   1.00    1.00    --  106.01  45.00-150.00   98
 15  \w     80.00 178.00   1.00    1.00    --  106.01  45.00   0.00   98
 16  \w     78.00 171.00   1.00    1.00    --  106.01  30.00  90.00   93
 17  \w     53.00 178.00   1.00    1.00    --  106.01  15.00 -60.00  125
;
_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      -0.0354639000
_diffrn_orient_matrix_UB_12      -0.0924614000
_diffrn_orient_matrix_UB_13      -0.0433758000
_diffrn_orient_matrix_UB_21      0.1368545000
_diffrn_orient_matrix_UB_22      -0.0340770000
_diffrn_orient_matrix_UB_23      0.0610149000
_diffrn_orient_matrix_UB_31      -0.0612611000
_diffrn_orient_matrix_UB_32      -0.0228506000
_diffrn_orient_matrix_UB_33      0.0847280000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20876
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.815
_diffrn_reflns_theta_min         4.354
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.721
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.669
_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            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0269
_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^)+(0.0337P)^2^+0.9040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0679
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3823
_reflns_number_total             4284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           m347
_cod_database_code               7709503
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H24 Br2 N2 S'
_reflns_odcompleteness_completeness 100.00
_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:
 C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              79704
_shelx_hkl_checksum              75232
_olex2_date_sample_data_collection 2020-09-15
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_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 1.516
_oxdiff_exptl_absorpt_empirical_full_min 0.788