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_7709506
_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 I2 N2 Se'
_chemical_formula_sum            'C21 H26 I2 N2 Se'
_chemical_formula_weight         639.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-15
_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                 97.730(2)
_cell_angle_gamma                90
_cell_formula_units_Z            40
_cell_length_a                   30.1615(4)
_cell_length_b                   44.2672(7)
_cell_length_c                   18.8321(3)
_cell_measurement_reflns_used    15324
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.4660
_cell_measurement_theta_min      3.0780
_cell_volume                     24915.5(7)
_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 0.978
_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    -87.00  -6.00   1.00    2.00    --  -41.68 125.00-120.00   81
  2  \w    -87.00  -6.00   1.00    2.00    --  -41.68 125.00-180.00   81
  3  \w   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00  30.00   99
  4  \w    -66.00  33.00   1.00    2.00    --  -41.68  38.00-180.00   99
  5  \w    103.00 178.00   1.00    2.00    --  106.01  77.00-180.00   75
  6  \w    103.00 178.00   1.00    2.00    --  106.01  77.00 -30.00   75
  7  \w     80.00 178.00   1.00    2.00    --  106.01  45.00 -60.00   98
  8  \w     33.00 132.00   1.00    2.00    --  106.01 -45.00  30.00   99
  9  \w     78.00 178.00   1.00    2.00    --  106.01  30.00 -90.00  100
 10  \w     23.00 107.00   1.00    2.00    --  106.01 -94.00  60.00   84
 11  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00-180.00  101
 12  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00 -60.00  101
 13  \w     14.00 115.00   1.00    2.00    --   41.68  57.00 150.00  101
 14  \w     77.00 178.00   1.00    2.00    --  106.01  61.00 150.00  101
 15  \w    103.00 178.00   1.00    2.00    --  106.01  77.00  30.00   75
 16  \w     23.00 107.00   1.00    2.00    --  106.01 -94.00-120.00   84
 17  \w     78.00 122.00   1.00    2.00    --  106.01  30.00  60.00   44
 18  \w    103.00 178.00   1.00    2.00    --  106.01  77.00  90.00   75
;
_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      -0.0215529000
_diffrn_orient_matrix_UB_12      -0.0075887000
_diffrn_orient_matrix_UB_13      -0.0767687000
_diffrn_orient_matrix_UB_21      0.0430770000
_diffrn_orient_matrix_UB_22      -0.0164603000
_diffrn_orient_matrix_UB_23      -0.0135664000
_diffrn_orient_matrix_UB_31      -0.0183442000
_diffrn_orient_matrix_UB_32      -0.0297031000
_diffrn_orient_matrix_UB_33      0.0272021000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -55
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            119022
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.323
_diffrn_reflns_theta_min         2.957
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    21.537
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.718
_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    1.704
_exptl_crystal_description       irregular
_exptl_crystal_F_000             12240
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.068
_refine_diff_density_max         1.143
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1201
_refine_ls_number_reflns         24869
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0146P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14544
_reflns_number_total             24869
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms266
_cod_database_code               7709506
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H26 N2 Se I2'
_shelx_estimated_absorpt_t_max   0.322
_shelx_estimated_absorpt_t_min   0.110
_reflns_odcompleteness_completeness 99.99
_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. Uiso/Uaniso restraints and constraints
Uanis(C104) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C23(H23A,H23B), C24(H24A,H24B), C44(H44A,H44B),
 C45(H45A,H45B), C65(H65A,H65B), C66(H66A,H66B), C86(H86A,H86B), C87(H87A,H87B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C15(H15), C17(H17), C27(H27), C29(H29), C36(H36), C38(H38),
 C48(H48), C50(H50), C57(H57), C59(H59), C69(H69), C71(H71), C78(H78), C80(H80),
  C90(H90), C92(H92), C99(H99), C101(H101)
3.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), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,
 H54C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C73(H73A,
 H73B,H73C), C74(H74A,H74B,H74C), C75(H75A,H75B,H75C), C82(H82A,H82B,H82C),
 C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C94(H94A,H94B,H94C), C95(H95A,H95B,
 H95C), C96(H96A,H96B,H96C), C103(H10D,H10E,H10F), C104(H10G,H10H,H10I),
 C105(H10J,H10K,H10L)
;
_shelx_res_checksum              75083
_shelx_hkl_checksum              41249
_shelx_fab_checksum              32257
_olex2_date_sample_data_collection 2020-02-03
_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 2.893
_oxdiff_exptl_absorpt_empirical_full_min 0.582