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_7709516
_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         'C15 H24 I2 N2 Se'
_chemical_formula_sum            'C15 H24 I2 N2 Se'
_chemical_formula_weight         565.12
_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     iterative
_audit_creation_date             2021-04-19
_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                107.039(4)
_cell_angle_beta                 101.991(3)
_cell_angle_gamma                91.225(3)
_cell_formula_units_Z            4
_cell_length_a                   10.4570(4)
_cell_length_b                   11.6249(5)
_cell_length_c                   16.1590(7)
_cell_measurement_reflns_used    11075
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.8080
_cell_measurement_theta_min      2.9030
_cell_volume                     1829.99(14)
_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    'olex2.solve (Bourhis et al., 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 0.977
_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    --  -41.55  38.00-180.00   99
  2  \w    -74.00  35.00   1.00    1.00    --  -41.55  77.00 -90.00  109
  3  \w   -116.00 -17.00   1.00    1.00    --  -41.55 -38.00   0.00   99
  4  \w      7.00  34.00   1.00    1.00    --   41.55  83.00   7.91   27
  5  \w      8.00  42.00   1.00    1.00    --   41.55  82.00 139.63   34
  6  \w     30.00 134.00   1.00    1.60    --  106.01 -30.00 -90.00  104
  7  \w     30.00 139.00   1.00    1.60    --  106.01 -77.00-180.00  109
  8  \w     33.00 132.00   1.00    1.60    --  106.01 -45.00  90.00   99
  9  \w     24.00 159.00   1.00    1.60    --  106.01 -15.00  90.00  135
 10  \w     30.00 139.00   1.00    1.60    --  106.01 -77.00 -60.00  109
 11  \w     23.00 107.00   1.00    1.60    --  106.01 -94.00 120.00   84
 12  \w     33.00 112.00   1.00    1.60    --  106.01-125.00 -60.00   79
 13  \w     80.00 178.00   1.00    1.60    --  106.01  45.00 -60.00   98
 14  \w     33.00 112.00   1.00    1.60    --  106.01-125.00  90.00   79
 15  \w     80.00 178.00   1.00    1.60    --  106.01  45.00  90.00   98
 16  \w   -116.00 -17.00   1.00    1.00    --  -41.55 -38.00 150.00   99
 17  \w    -66.00  33.00   1.00    1.00    --  -41.55  38.00  90.00   99
 18  \w      8.00  42.00   1.00    1.00    --   41.55  80.00-101.31   34
 19  \w      8.00  42.00   1.00    1.00    --   41.55  82.00 -54.61   34
 20  \w      7.00  33.00   1.00    1.00    --   41.55  84.00  61.62   26
 21  \w     78.00 178.00   1.00    1.60    --  106.01  57.00  -2.97  100
 22  \w     77.00 178.00   1.00    1.60    --  106.01  61.00-150.00  101
 23  \w     53.00 178.00   1.00    1.60    --  106.01  15.00-120.00  125
 24  \w     75.00 178.00   1.00    1.60    --  106.01  69.00 -47.57  103
 25  \w     76.00 178.00   1.00    1.60    --  106.01  65.00  36.64  102
 26  \w     77.00 178.00   1.00    1.60    --  106.01  61.00-120.00  101
 27  \w     77.00 178.00   1.00    1.60    --  106.01  63.00 145.30  101
 28  \w     78.00 178.00   1.00    1.60    --  106.01  58.00 -90.95  100
 29  \w     75.00 178.00   1.00    1.60    --  106.01  72.00  88.22  103
 30  \w     77.00 178.00   1.00    1.60    --  106.01  61.00 120.00  101
 31  \w      7.00  33.00   1.00    1.00    --   41.55  84.00 109.15   26
 32  \w      7.00  34.00   1.00    1.00    --   41.55  83.00-167.84   27
 33  \w      7.00  34.00   1.00    1.00    --   41.55  83.00  37.46   27
 34  \w     27.00  98.00   1.00    1.00    --   41.55-125.00  60.00   71
 35  \w      8.00  42.00   1.00    1.00    --   41.55  80.00 -21.06   34
 36  \w     77.00 178.00   1.00    1.60    --  106.01  61.00-180.00  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      -0.1482524000
_diffrn_orient_matrix_UB_12      -0.0047001000
_diffrn_orient_matrix_UB_13      -0.0389557000
_diffrn_orient_matrix_UB_21      -0.0108426000
_diffrn_orient_matrix_UB_22      0.1101154000
_diffrn_orient_matrix_UB_23      0.0784479000
_diffrn_orient_matrix_UB_31      0.0276360000
_diffrn_orient_matrix_UB_32      0.0849359000
_diffrn_orient_matrix_UB_33      -0.0528779000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34175
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.062
_diffrn_reflns_theta_min         2.935
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    29.205
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.513
_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    2.051
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.049
_refine_diff_density_max         1.261
_refine_diff_density_min         -1.593
_refine_diff_density_rms         0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         7269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0566P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5888
_reflns_number_total             7269
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms282
_cod_database_code               7709516
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H24 N2 Se I2'
_shelx_estimated_absorpt_t_max   0.329
_shelx_estimated_absorpt_t_min   0.124
_reflns_odcompleteness_completeness 99.94
_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
2.a Ternary CH refined with riding coordinates:
 C4(H4), C10(H10), C19(H19), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,
 H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B),
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
  C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C17(H17), C18(H18)
;
_shelx_res_checksum              29266
_shelx_hkl_checksum              37811
_olex2_date_sample_data_collection 2020-11-19
_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 3.275
_oxdiff_exptl_absorpt_empirical_full_min 0.530