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_7709502
_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         'C29 H40 Br N2 S, Br3'
_chemical_formula_sum            'C29 H40 Br4 N2 S'
_chemical_formula_weight         768.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-06
_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                 110.132(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7651(2)
_cell_length_b                   16.9691(3)
_cell_length_c                   10.1288(2)
_cell_measurement_reflns_used    6503
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.5340
_cell_measurement_theta_min      4.6330
_cell_volume                     1575.85(6)
_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 0.994
_diffrn_measured_fraction_theta_max 0.982
_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   -130.00  46.00   1.00    1.00    --  -41.68   0.00  60.00  176
  2  \w     27.00  98.00   1.00    1.00    --   41.68-125.00-120.00   71
  3  \w     34.00 135.00   1.00    6.00    --  106.01 -61.00  90.00  101
  4  \w    103.00 178.00   1.00    6.00    --  106.01  77.00-150.00   75
  5  \w    103.00 178.00   1.00    6.00    --  106.01  77.00   0.00   75
  6  \w    103.00 178.00   1.00    6.00    --  106.01  77.00 120.00   75
  7  \w    103.00 178.00   1.00    6.00    --  106.01  77.00 -90.00   75
  8  \w    103.00 178.00   1.00    6.00    --  106.01  77.00 150.00   75
  9  \w    103.00 178.00   1.00    6.00    --  106.01  77.00 -60.00   75
 10  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -30.00  101
 11  \w     14.00 115.00   1.00    1.00    --   41.68  57.00 -90.00  101
 12  \w     33.00 112.00   1.00    6.00    --  106.01-125.00 -30.00   79
 13  \w     78.00 178.00   1.00    6.00    --  106.01  30.00-120.00  100
 14  \w     33.00 112.00   1.00    6.00    --  106.01-125.00  90.00   79
 15  \w     78.00 178.00   1.00    6.00    --  106.01  30.00  90.00  100
 16  \w    -87.00  -6.00   1.00    1.00    --  -41.68 125.00  30.00   81
 17  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  60.00  101
 18  \w     77.00 112.00   1.00    6.00    --  106.01  61.00   0.00   35
;
_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      -0.0064072000
_diffrn_orient_matrix_UB_12      0.0764734000
_diffrn_orient_matrix_UB_13      0.0796819000
_diffrn_orient_matrix_UB_21      0.1513968000
_diffrn_orient_matrix_UB_22      -0.0184981000
_diffrn_orient_matrix_UB_23      0.1084683000
_diffrn_orient_matrix_UB_31      0.0725173000
_diffrn_orient_matrix_UB_32      0.0453291000
_diffrn_orient_matrix_UB_33      -0.0901839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15068
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.786
_diffrn_reflns_theta_min         4.650
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.999
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.774
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       irregular
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.062
_refine_diff_density_max         1.392
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0415P)^2^+2.9707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2866
_reflns_number_total             3254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms--349
_cod_database_code               7709502
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C29 H40 N2 Se Br2'
_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.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              65277
_shelx_hkl_checksum              87677
_olex2_date_sample_data_collection 2021-10-05
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.791