Charge-Transfer Adducts of Chalcogenourea Derivatives of N-Heterocyclic Carbenes with Iodine Monochloride
Saab, Marina; Nahra, Fady; Van Hecke, Kristof; Molbank 2022 (2022) M1344–; doi:10.3390/M1344

data_1566570
_publ_section_title
;
 Charge-Transfer Adducts of Chalcogenourea Derivatives of N-Heterocyclic
 Carbenes with Iodine Monochloride
;
_journal_issue                   1
_journal_name_full               Molbank
_journal_page_first              M1344
_journal_paper_doi               10.3390/M1344
_journal_volume                  2022
_journal_year                    2022
_chemical_formula_moiety         'C29 H40 Cl I N2 Se, C H2 Cl2'
_chemical_formula_sum            'C30 H42 Cl3 I N2 Se'
_chemical_formula_weight         742.87
_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     dual
_audit_creation_date             2020-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.3990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.74100(10)
_cell_length_b                   16.92180(10)
_cell_length_c                   19.8068(2)
_cell_measurement_reflns_used    13346
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.8050
_cell_measurement_theta_min      3.4170
_cell_volume                     3237.67(5)
_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 0.982
_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 -90.00   81
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00  60.00   99
  3  \w    -21.00  74.00   1.00    1.00    --   41.68 -77.00 -90.00   95
  4  \w     33.00 132.00   1.00    7.00    --  106.01 -45.00-180.00   99
  5  \w    103.00 178.00   1.00    7.00    --  106.01  77.00-150.00   75
  6  \w     34.00 120.00   1.00    7.00    --  106.01-135.00 -74.00   86
  7  \w     78.00 178.00   1.00    7.00    --  106.01  30.00   0.00  100
  8  \w     23.00 107.00   1.00    7.00    --  106.01 -94.00 120.00   84
  9  \w     33.00 112.00   1.00    7.00    --  106.01-125.00  90.00   79
 10  \w   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00-180.00   99
 11  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -60.00  101
 12  \w      8.00  42.00   1.00    1.00    --   41.68  82.00-112.12   34
 13  \w     81.00 178.00   1.00    7.00    --  106.01  38.00  78.65   97
 14  \w     76.00 178.00   1.00    7.00    --  106.01  66.00 -78.79  102
 15  \w     97.00 178.00   1.00    7.00    --  106.01 125.00  90.00   81
 16  \w     74.00 109.00   1.00    7.00    --  106.01  73.00-123.41   35
 17  \w     76.00 178.00   1.00    7.00    --  106.01  64.00-163.84  102
 18  \w     80.00 178.00   1.00    7.00    --  106.01  45.00 150.00   98
;
_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      -0.0475117000
_diffrn_orient_matrix_UB_12      -0.0676124000
_diffrn_orient_matrix_UB_13      -0.0496778000
_diffrn_orient_matrix_UB_21      -0.0512139000
_diffrn_orient_matrix_UB_22      0.0610030000
_diffrn_orient_matrix_UB_23      -0.0553280000
_diffrn_orient_matrix_UB_31      0.1433172000
_diffrn_orient_matrix_UB_32      -0.0006153000
_diffrn_orient_matrix_UB_33      -0.0249626000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.873
_diffrn_reflns_theta_min         3.447
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.489
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.774
_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    1.524
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.052
_refine_diff_density_max         1.958
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0362P)^2^+1.6879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0697
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5842
_reflns_number_total             6440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            s8.cif
_cod_data_source_block           ms453
_cod_database_code               1566570
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C29 H40 Cl I N2 Se'
_shelx_estimated_absorpt_t_max   0.586
_shelx_estimated_absorpt_t_min   0.339
_reflns_odcompleteness_completeness 99.92
_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:
 C12(H12), C15(H15), C24(H24), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              31770
_shelx_hkl_checksum              89075
_olex2_date_sample_data_collection 2020-12-01
_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 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.781