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_7709514
_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         '2(C15 H24 I2 N2 S), C H2 Cl2'
_chemical_formula_sum            'C31 H50 Cl2 I4 N4 S2'
_chemical_formula_weight         1121.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-18
_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                 117.447(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.8192(6)
_cell_length_b                   9.6293(3)
_cell_length_c                   15.9429(6)
_cell_measurement_reflns_used    3852
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.5150
_cell_measurement_theta_min      3.3740
_cell_volume                     2018.95(16)
_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 0.963
_diffrn_measured_fraction_theta_max 0.922
_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    -70.00  31.00   1.00    2.25    --  -41.68  57.00 -30.00  101
  2  \w    -87.00  -6.00   1.00    2.25    --  -41.68 125.00 150.00   81
  3  \w     17.00 116.00   1.00    2.25    --   41.68  38.00  60.00   99
  4  \w     30.00 134.00   1.00    7.50    --  106.01 -30.00 -90.00  104
  5  \w     33.00 112.00   1.00    7.50    --  106.01-125.00  90.00   79
  6  \w     18.00 178.00   1.00    7.50    --  106.01   0.00   0.00  160
  7  \w     14.00 115.00   1.00    2.25    --   41.68  57.00 -60.00  101
  8  \w     14.00 115.00   1.00    2.25    --   41.68  57.00-150.00  101
  9  \w     77.00  96.00   1.00    7.50    --  106.01  61.00  60.00   19
;
_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      -0.0462490000
_diffrn_orient_matrix_UB_12      0.0535063000
_diffrn_orient_matrix_UB_13      0.0628174000
_diffrn_orient_matrix_UB_21      0.1046718000
_diffrn_orient_matrix_UB_22      -0.0123400000
_diffrn_orient_matrix_UB_23      0.0876916000
_diffrn_orient_matrix_UB_31      0.0251598000
_diffrn_orient_matrix_UB_32      0.1502278000
_diffrn_orient_matrix_UB_33      -0.0152012000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9337
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.947
_diffrn_reflns_theta_min         4.592
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    26.621
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.745
_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    1.845
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.054
_refine_diff_density_max         3.132
_refine_diff_density_min         -1.709
_refine_diff_density_rms         0.366
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0561
_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^)+(0.1015P)^2^+1.8576P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1686
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3101
_reflns_number_total             3769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms---359
_cod_original_cell_volume        2018.95(15)
_cod_database_code               7709514
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H24 N2 S I2'
_shelx_estimated_absorpt_t_max   0.327
_shelx_estimated_absorpt_t_min   0.118
_reflns_odcompleteness_completeness 96.70
_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. Others
 Fixed Sof: H16A(0.5) H16B(0.5)
3.a Ternary CH refined with riding coordinates:
 C4(H4), C10(H10)
3.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),
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_shelx_res_checksum              21999
_shelx_hkl_checksum              67174
_olex2_date_sample_data_collection 2021-10-18
_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 2.190
_oxdiff_exptl_absorpt_empirical_full_min 0.472