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_7709498
_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 Br2 N2 Se, C H2 Cl2'
_chemical_formula_sum            'C30 H42 Br2 Cl2 N2 Se'
_chemical_formula_weight         740.32
_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             2020-02-05
_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                77.201(2)
_cell_angle_beta                 77.009(2)
_cell_angle_gamma                73.293(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7087(3)
_cell_length_b                   12.5412(3)
_cell_length_c                   15.1640(3)
_cell_measurement_reflns_used    15223
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      72.9860
_cell_measurement_theta_min      2.9950
_cell_volume                     1698.62(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 0.984
_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    -66.00  33.00   1.00    1.00    --  -41.68  38.00  60.00   99
  2  \w    -74.00  34.00   1.00    1.00    --  -41.68  77.00 150.00  108
  3  \w   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00-120.00   99
  4  \w     27.00  98.00   1.00    1.00    --   41.68-125.00-150.00   71
  5  \w     23.00 107.00   1.00    1.20    --  106.01 -94.00  90.00   84
  6  \w     33.00 112.00   1.00    1.20    --  106.01-125.00  30.00   79
  7  \w    103.00 178.00   1.00    1.20    --  106.01  77.00 -60.00   75
  8  \w    103.00 178.00   1.00    1.20    --  106.01  77.00-180.00   75
  9  \w     23.00 107.00   1.00    1.20    --  106.01 -94.00 150.00   84
 10  \w    103.00 178.00   1.00    1.20    --  106.01  77.00 -90.00   75
 11  \w     77.00 178.00   1.00    1.20    --  106.01  61.00 -30.00  101
 12  \w     33.00 112.00   1.00    1.20    --  106.01-125.00 -60.00   79
 13  \w     34.00 135.00   1.00    1.20    --  106.01 -61.00-180.00  101
 14  \w    103.00 178.00   1.00    1.20    --  106.01  77.00-120.00   75
 15  \w     80.00 178.00   1.00    1.20    --  106.01  45.00-120.00   98
 16  \w     37.00 127.00   1.00    1.20    --  106.01-144.00  81.38   90
 17  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  60.00  101
 18  \w   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00 120.00   99
 19  \w      7.00  34.00   1.00    1.00    --   41.68  83.00-136.75   27
 20  \w      8.00  42.00   1.00    1.00    --   41.68  81.00  25.85   34
 21  \w     77.00 178.00   1.00    1.20    --  106.01  61.00  90.00  101
 22  \w     77.00 178.00   1.00    1.20    --  106.01  61.00   0.00  101
 23  \w     80.00 178.00   1.00    1.20    --  106.01  45.00-180.00   98
 24  \w     80.00 178.00   1.00    1.20    --  106.01  45.00-150.00   98
 25  \w     53.00 178.00   1.00    1.20    --  106.01  15.00 120.00  125
 26  \w     77.00 178.00   1.00    1.20    --  106.01  62.00  38.33  101
 27  \w     77.00 178.00   1.00    1.20    --  106.01  61.00 120.00  101
 28  \w     76.00 178.00   1.00    1.20    --  106.01  64.00 -81.09  102
 29  \w      9.00  42.00   1.00    1.00    --   41.68  80.00  49.66   33
 30  \w      6.00  83.00   1.00    1.00    --   41.68 -99.00 -90.00   77
 31  \w      7.00  33.00   1.00    1.00    --   41.68  84.00 -81.64   26
 32  \w      9.00  42.00   1.00    1.00    --   41.68  80.00 -35.25   33
 33  \w     77.00 178.00   1.00    1.20    --  106.01  61.00-180.00  101
 34  \w     74.00 178.00   1.00    1.20    --  106.01  73.00 130.42  104
 35  \w     77.00 178.00   1.00    1.20    --  106.01  61.00-120.00  101
 36  \w     77.00 178.00   1.00    1.20    --  106.01  61.00 -90.00  101
 37  \w     77.00 178.00   1.00    1.20    --  106.01  61.00 -60.00  101
 38  \w     77.00 178.00   1.00    1.20    --  106.01  61.00-150.00  101
 39  \w     77.00 178.00   1.00    1.20    --  106.01  61.00  21.36  101
 40  \w     77.00 178.00   1.00    1.20    --  106.01  61.00  60.00  101
 41  \w      9.00  42.00   1.00    1.00    --   41.68  80.00 152.99   33
;
_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      0.1355836000
_diffrn_orient_matrix_UB_12      -0.0747762000
_diffrn_orient_matrix_UB_13      -0.0514391000
_diffrn_orient_matrix_UB_21      0.0140371000
_diffrn_orient_matrix_UB_22      -0.0880344000
_diffrn_orient_matrix_UB_23      0.0883701000
_diffrn_orient_matrix_UB_31      -0.0985339000
_diffrn_orient_matrix_UB_32      -0.0598831000
_diffrn_orient_matrix_UB_33      -0.0270473000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.854
_diffrn_reflns_theta_min         3.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.846
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.447
_exptl_crystal_description       needle
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0321P)^2^+1.3234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0706
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5918
_reflns_number_total             6767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms242-1
_cod_database_code               7709498
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C29 H40 Br2 N2 Se'
_shelx_estimated_absorpt_t_max   0.759
_shelx_estimated_absorpt_t_min   0.464
_reflns_odcompleteness_completeness 99.93
_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
2.a Ternary CH refined with riding coordinates:
 C12(H12), C15(H15), C24(H24), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              57952
_shelx_hkl_checksum              31038
_shelx_fab_checksum              44236
_olex2_date_sample_data_collection 2019-11-13
_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 1.368
_oxdiff_exptl_absorpt_empirical_full_min 0.783