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_7709505
_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         'C69 H56 Cl2 N2 Se'
_chemical_formula_sum            'C69 H56 Cl2 N2 Se'
_chemical_formula_weight         1063.02
_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             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                104.727(3)
_cell_angle_beta                 92.152(3)
_cell_angle_gamma                96.504(3)
_cell_formula_units_Z            2
_cell_length_a                   10.5501(4)
_cell_length_b                   13.3094(5)
_cell_length_c                   21.9568(9)
_cell_measurement_reflns_used    10547
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.7250
_cell_measurement_theta_min      3.4440
_cell_volume                     2955.5(2)
_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 0.998
_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   -116.00 -17.00   1.00    2.80    --  -41.68 -38.00 -90.00   99
  2  \w   -116.00 -17.00   1.00    2.80    --  -41.68 -38.00-180.00   99
  3  \w    -87.00  -6.00   1.00    2.80    --  -41.68 125.00 -30.00   81
  4  \w      7.00  33.00   1.00    2.80    --   41.68  84.00-177.49   26
  5  \w     14.00 115.00   1.00    2.80    --   41.68  57.00 120.00  101
  6  \w     23.00 107.00   1.00    6.00    --  106.01 -94.00  90.00   84
  7  \w     23.00 107.00   1.00    6.00    --  106.01 -94.00 -90.00   84
  8  \w    103.00 178.00   1.00    6.00    --  106.01  77.00 -60.00   75
  9  \w    103.00 178.00   1.00    6.00    --  106.01  77.00  90.00   75
 10  \w     30.00 139.00   1.00    6.00    --  106.01 -77.00-150.00  109
 11  \w    103.00 178.00   1.00    6.00    --  106.01  77.00 150.00   75
 12  \w     23.00 107.00   1.00    6.00    --  106.01 -94.00-180.00   84
 13  \w     33.00 132.00   1.00    6.00    --  106.01 -45.00   0.00   99
 14  \w     53.00 178.00   1.00    6.00    --  106.01  15.00 -90.00  125
 15  \w    103.00 178.00   1.00    6.00    --  106.01  77.00  60.00   75
 16  \w     26.00 108.00   1.00    6.00    --  106.01-102.00  23.20   82
 17  \w    -87.00  -6.00   1.00    2.80    --  -41.68 125.00-180.00   81
 18  \w   -116.00 -17.00   1.00    2.80    --  -41.68 -38.00   0.00   99
 19  \w      8.00  42.00   1.00    2.80    --   41.68  82.00-127.25   34
 20  \w      7.00  34.00   1.00    2.80    --   41.68  83.00  -0.11   27
 21  \w      8.00  42.00   1.00    2.80    --   41.68  82.00  59.68   34
 22  \w     77.00 178.00   1.00    6.00    --  106.01  61.00 150.00  101
 23  \w     75.00 176.00   1.00    6.00    --  106.01  69.00 111.08  101
 24  \w     78.00 178.00   1.00    6.00    --  106.01  30.00  30.00  100
 25  \w     78.00 178.00   1.00    6.00    --  106.01  54.00  56.36  100
 26  \w     77.00 178.00   1.00    6.00    --  106.01  61.00 -90.00  101
 27  \w     77.00 178.00   1.00    6.00    --  106.01  61.00  90.00  101
 28  \w     78.00  80.00   1.00    6.00    --  106.01  56.00 -39.24    2
;
_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      0.1188951000
_diffrn_orient_matrix_UB_12      -0.0110715000
_diffrn_orient_matrix_UB_13      0.0395239000
_diffrn_orient_matrix_UB_21      0.0706900000
_diffrn_orient_matrix_UB_22      0.0991987000
_diffrn_orient_matrix_UB_23      -0.0132799000
_diffrn_orient_matrix_UB_31      -0.0507001000
_diffrn_orient_matrix_UB_32      0.0677931000
_diffrn_orient_matrix_UB_33      0.0595794000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            42669
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.011
_diffrn_reflns_theta_min         3.462
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.001
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.804
_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            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.064
_refine_diff_density_max         1.953
_refine_diff_density_min         -1.032
_refine_diff_density_rms         0.083
_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     669
_refine_ls_number_reflns         11737
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0674
_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^)+(0.0757P)^2^+5.2670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1772
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9275
_reflns_number_total             11737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms456-3
_cod_database_code               7709505
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C69 H56 N2 Se I Cl'
_reflns_odcompleteness_completeness 99.97
_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. Uiso/Uaniso restraints and constraints
Uanis(C69) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C66)
\\sim Ueq, Uanis(C65) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C11(H11), C24(H24), C44(H44), C57(H57)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35),
 C36(H36), C39(H39), C42(H42), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50),
  C52(H52), C53(H53), C54(H54), C55(H55), C56(H56), C59(H59), C60(H60),
 C61(H61), C62(H62), C63(H63), C65(H65), C66(H66), C67(H67), C68(H68), C69(H69)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C41(H41A,H41B,H41C)
;
_shelx_res_checksum              93001
_shelx_hkl_checksum              64518
_shelx_fab_checksum              15073
_olex2_date_sample_data_collection 2021-03-16
_olex2_exptl_crystal_mounting_method 'Mounyted 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 1.696
_oxdiff_exptl_absorpt_empirical_full_min 0.672