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_7709511
_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         'C27 H34 Cl2 I2 N2 Se'
_chemical_formula_sum            'C27 H34 Cl2 I2 N2 Se'
_chemical_formula_weight         790.22
_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             2020-11-17
_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                74.003(2)
_cell_angle_beta                 89.506(2)
_cell_angle_gamma                73.080(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6805(2)
_cell_length_b                   10.5911(2)
_cell_length_c                   18.1694(4)
_cell_measurement_reflns_used    11626
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.6780
_cell_measurement_theta_min      4.5140
_cell_volume                     1531.57(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 0.999
_diffrn_measured_fraction_theta_max 0.980
_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   -114.00 -13.00   1.00    1.00    --  -41.43 -57.00  90.00  101
  2  \w    -70.00  32.00   1.00    1.00    --  -41.43  57.00   0.00  102
  3  \w    -70.00  32.00   1.00    1.00    --  -41.43  57.00-120.00  102
  4  \w    -21.00  74.00   1.00    1.00    --   41.43 -77.00 -30.00   95
  5  \w     34.00 135.00   1.00    1.00    --  106.01 -61.00  60.00  101
  6  \w    103.00 178.00   1.00    1.00    --  106.01  77.00-180.00   75
  7  \w     23.00 107.00   1.00    1.00    --  106.01 -94.00  30.00   84
  8  \w     23.00 107.00   1.00    1.00    --  106.01 -94.00 120.00   84
  9  \w     33.00 132.00   1.00    1.00    --  106.01 -45.00-120.00   99
 10  \w    103.00 178.00   1.00    1.00    --  106.01  77.00 -30.00   75
 11  \w    103.00 178.00   1.00    1.00    --  106.01  77.00  30.00   75
 12  \w     24.00 159.00   1.00    1.00    --  106.01 -15.00   0.00  135
 13  \w     33.00 112.00   1.00    1.00    --  106.01-125.00-120.00   79
 14  \w     33.00 112.00   1.00    1.00    --  106.01-125.00  30.00   79
 15  \w     27.00 108.00   1.00    1.00    --  106.01-104.00 -96.05   81
 16  \w   -114.00 -13.00   1.00    1.00    --  -41.43 -57.00-120.00  101
 17  \w   -116.00 -17.00   1.00    1.00    --  -41.43 -38.00 -30.00   99
 18  \w      8.00  42.00   1.00    1.00    --   41.43  79.00-115.96   34
 19  \w      7.00  34.00   1.00    1.00    --   41.43  83.00   0.38   27
 20  \w     77.00 138.00   1.00    1.00    --  106.01  61.00  60.00   61
 21  \w     77.00 178.00   1.00    1.00    --  106.01  61.00  30.00  101
 22  \w     79.00 178.00   1.00    1.00    --  106.01  52.00 175.19   99
 23  \w     77.00 178.00   1.00    1.00    --  106.01  61.00-150.00  101
 24  \w     78.00 178.00   1.00    1.00    --  106.01  30.00 120.00  100
 25  \w     75.00 178.00   1.00    1.00    --  106.01  69.00 134.59  103
 26  \w     77.00 178.00   1.00    1.00    --  106.01  61.00 -30.00  101
 27  \w     77.00 178.00   1.00    1.00    --  106.01  61.00 -90.00  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      0.0136439000
_diffrn_orient_matrix_UB_12      0.1060744000
_diffrn_orient_matrix_UB_13      0.0410514000
_diffrn_orient_matrix_UB_21      -0.1026009000
_diffrn_orient_matrix_UB_22      0.1174248000
_diffrn_orient_matrix_UB_23      -0.0673720000
_diffrn_orient_matrix_UB_31      -0.1546230000
_diffrn_orient_matrix_UB_32      -0.0112309000
_diffrn_orient_matrix_UB_33      0.0400409000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23063
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.773
_diffrn_reflns_theta_min         4.536
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.219
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.226
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_description       irregular
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.856
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.091
_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     315
_refine_ls_number_reflns         6085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0334P)^2^+1.1721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5664
_reflns_number_total             6085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms267
_cod_database_code               7709511
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C27 H34 N2 Se I2'
_reflns_odcompleteness_completeness 99.91
_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), C22(H22), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
;
_shelx_res_checksum              93031
_shelx_hkl_checksum              57728
_olex2_date_sample_data_collection 2020-11-13
_olex2_exptl_crystal_mounting_method 'mounted in 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 2.088
_oxdiff_exptl_absorpt_empirical_full_min 0.719