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_7709517
_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         'C54 H76 I N4 Se2, I5, C H2 Cl2'
_chemical_formula_sum            'C55 H78 Cl2 I6 N4 Se2'
_chemical_formula_weight         1785.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 90.7280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.67600(10)
_cell_length_b                   32.7882(2)
_cell_length_c                   18.84640(10)
_cell_measurement_reflns_used    19471
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.8740
_cell_measurement_theta_min      3.5420
_cell_volume                     6596.59(8)
_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 0.979
_diffrn_measured_fraction_theta_max 0.956
_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    1.00    --  -41.68 125.00-120.00   81
  2  \w    -74.00  34.00   1.00    1.00    --  -41.68  77.00-180.00  108
  3  \w     80.00 178.00   1.00    2.00    --  106.01  45.00   0.00   98
  4  \w     33.00 112.00   1.00    2.00    --  106.01-125.00   0.00   79
  5  \w    103.00 178.00   1.00    2.00    --  106.01  77.00-120.00   75
  6  \w    103.00 178.00   1.00    2.00    --  106.01  77.00  90.00   75
  7  \w     33.00 112.00   1.00    2.00    --  106.01-125.00 -60.00   79
  8  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-150.00  101
  9  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  90.00  101
 10  \w     80.00 178.00   1.00    2.00    --  106.01  45.00-180.00   98
 11  \w     23.00  54.00   1.00    2.00    --  106.01 -94.00  60.00   31
 12  \w     77.00 178.00   1.00    2.00    --  106.01  61.00 -60.00  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      -0.1087079000
_diffrn_orient_matrix_UB_12      0.0231577000
_diffrn_orient_matrix_UB_13      0.0348446000
_diffrn_orient_matrix_UB_21      -0.0870703000
_diffrn_orient_matrix_UB_22      -0.0367222000
_diffrn_orient_matrix_UB_23      -0.0136409000
_diffrn_orient_matrix_UB_31      0.0377601000
_diffrn_orient_matrix_UB_32      -0.0179706000
_diffrn_orient_matrix_UB_33      0.0726840000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            41544
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.906
_diffrn_reflns_theta_min         2.695
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    24.459
_exptl_absorpt_correction_T_max  0.418
_exptl_absorpt_correction_T_min  0.036
_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    1.798
_exptl_crystal_description       cube
_exptl_crystal_F_000             3424
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.103
_refine_diff_density_max         1.852
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     638
_refine_ls_number_reflns         12790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0637P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11555
_reflns_number_total             12790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms257
_cod_database_code               7709517
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C27 H38 I2 N2 Se'
_reflns_odcompleteness_completeness 97.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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), C37(H37), C40(H40), C49(H49), C52(H52)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C29(H29A,H29B), C30(H30A,H30B), C55(H55A,H55B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C33(H33), C34(H34),
 C35(H35), C45(H45), C46(H46), C47(H47)
2.d 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(H24C,H24A,H24B), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C53(H53A,H53B,
 H53C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              59913
_shelx_hkl_checksum              6252
_olex2_date_sample_data_collection 2019-11-19
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 2.970
_oxdiff_exptl_absorpt_empirical_full_min 0.590