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_7709508
_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 H26 Cl N2, H O4 S'
_chemical_formula_sum            'C21 H27 Cl N2 O4 S'
_chemical_formula_weight         438.95
_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             2020-12-03
_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                78.387(5)
_cell_angle_beta                 74.490(5)
_cell_angle_gamma                66.020(6)
_cell_formula_units_Z            4
_cell_length_a                   11.7200(7)
_cell_length_b                   13.2714(8)
_cell_length_c                   15.9571(8)
_cell_measurement_reflns_used    4124
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.3160
_cell_measurement_theta_min      4.2020
_cell_volume                     2173.0(2)
_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 0.983
_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    -74.00  34.00   1.00    1.00    --  -41.68  77.00   0.00  108
  2  \w    -66.00  33.00   1.00    1.00    --  -41.68  38.00 -90.00   99
  3  \w   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00  90.00   99
  4  \w      8.00  42.00   1.00    1.00    --   41.68  81.00  73.38   34
  5  \w      7.00  34.00   1.00    1.00    --   41.68  83.00-122.17   27
  6  \w     81.00 178.00   1.00    3.70    --  106.01  40.00  48.75   97
  7  \w     33.00 132.00   1.00    3.70    --  106.01 -45.00-180.00   99
  8  \w     34.00 135.00   1.00    3.70    --  106.01 -61.00  90.00  101
  9  \w     26.00 108.00   1.00    3.70    --  106.01-102.00-147.00   82
 10  \w     33.00 132.00   1.00    3.70    --  106.01 -45.00 -30.00   99
 11  \w     97.00 178.00   1.00    3.70    --  106.01 125.00 -90.00   81
 12  \w     33.00 112.00   1.00    3.70    --  106.01-125.00  30.00   79
 13  \w     33.00 112.00   1.00    3.70    --  106.01-125.00  90.00   79
 14  \w     23.00 107.00   1.00    3.70    --  106.01 -94.00  90.00   84
 15  \w     23.00 107.00   1.00    3.70    --  106.01 -94.00 -60.00   84
 16  \w     18.00 178.00   1.00    3.70    --  106.01   0.00  30.00  160
 17  \w    -87.00  -6.00   1.00    1.00    --  -41.68 125.00  60.00   81
 18  \w     10.00  36.00   1.00    1.00    --   41.68  75.00-168.86   26
 19  \w      8.00  42.00   1.00    1.00    --   41.68  81.00 -31.90   34
 20  \w     17.00 116.00   1.00    1.00    --   41.68  38.00 -60.00   99
 21  \w      8.00  42.00   1.00    1.00    --   41.68  81.00  43.15   34
 22  \w     77.00 178.00   1.00    3.70    --  106.01  61.00  90.00  101
 23  \w     53.00 178.00   1.00    3.70    --  106.01  15.00-150.00  125
 24  \w     77.00 178.00   1.00    3.70    --  106.01  61.00 -10.35  101
 25  \w     77.00 178.00   1.00    3.70    --  106.01  61.00 -60.00  101
 26  \w     77.00 178.00   1.00    3.70    --  106.01  62.00-167.04  101
 27  \w     77.00 178.00   1.00    3.70    --  106.01  61.00-120.00  101
;
_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      -0.1392908000
_diffrn_orient_matrix_UB_12      0.0678165000
_diffrn_orient_matrix_UB_13      -0.0088912000
_diffrn_orient_matrix_UB_21      0.0467911000
_diffrn_orient_matrix_UB_22      0.0389302000
_diffrn_orient_matrix_UB_23      -0.0959178000
_diffrn_orient_matrix_UB_31      -0.0059976000
_diffrn_orient_matrix_UB_32      -0.1010308000
_diffrn_orient_matrix_UB_33      -0.0295245000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_unetI/netI     0.1002
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32389
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.832
_diffrn_reflns_theta_min         2.890
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.702
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.825
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       irregular
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         8649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0169P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5776
_reflns_number_total             8649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms342
_cod_database_code               7709508
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H24 N2 S Cl2'
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C15(H15), C17(H17), C27(H27), C29(H29), C36(H36), C38(H38)
2.c 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), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C33(H33A,H33B,H33C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8A)
;
_shelx_res_checksum              26594
_shelx_hkl_checksum              52100
_olex2_date_sample_data_collection 2020-11-30
_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 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.902