IBzH (IBenzhydryl): sterically-flexible N-aliphatic N-heterocyclic carbenes (NHCs) for iron-catalyzed C(sp3)–C(sp2) cross-coupling of unactivated haloalkanes
Kardela, Marlena; Dziuk, Błażej; Szostak, Roman; Szostak, Michal; Bisz, Elwira; Catalysis Science & Technology 14 (2024) 7002–7008; doi:10.1039/D4CY01315H

data_1573094
_publ_section_title
;
 IBzH (IBenzhydryl): sterically-flexible N-aliphatic N-heterocyclic
 carbenes (NHCs) for iron-catalyzed C(sp3)--C(sp2) cross-coupling of
 unactivated haloalkanes
;
_journal_issue                   24
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              7002
_journal_page_last               7008
_journal_paper_doi               10.1039/D4CY01315H
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C29 H24 N2 Se'
_chemical_formula_sum            'C29 H24 N2 Se'
_chemical_formula_weight         479.46
_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
_audit_creation_date             2024-10-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-10-23 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.9350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.30910(10)
_cell_length_b                   25.5056(2)
_cell_length_c                   11.35770(10)
_cell_measurement_reflns_used    17831
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.279
_cell_measurement_theta_min      3.466
_cell_volume                     2290.06(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.42a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.42a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.42a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17831
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.279
_diffrn_reflns_theta_min         3.466
_exptl_absorpt_coefficient_mu    2.353
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00116(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0244
_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^)+(0.0282P)^2^+1.4481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0627
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4302
_reflns_number_total             4442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cy01315h2.cif
_cod_data_source_block           bdbzh
_cod_depositor_comments
'Adding full bibliography for 1573093--1573094.cif.'
_cod_database_code               1573094
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
;
_shelx_res_checksum              22630
_shelx_hkl_checksum              64567
_olex2_submission_special_instructions 'No special instructions were received'