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#$Date: 2025-01-06 11:41:46 +0200 (Mon, 06 Jan 2025) $
#$Revision: 297069 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/30/1573093.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1573093
loop_
_publ_author_name
'Kardela, Marlena'
'Dziuk, Błażej'
'Szostak, Roman'
'Szostak, Michal'
'Bisz, Elwira'
_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 & 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 Ag Cl N2'
_chemical_formula_sum            'C29 H24 Ag Cl N2'
_chemical_formula_weight         543.82
_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
_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                 91.317(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0868(11)
_cell_length_b                   15.0378(14)
_cell_length_c                   12.4442(9)
_cell_measurement_reflns_used    4664
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.000
_cell_measurement_theta_min      2.063
_cell_volume                     2448.3(4)
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_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    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       ω--scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4664
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.063
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0284P)²+1.0620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1716
_reflns_number_total             2408
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cy01315h2.cif
_cod_data_source_block           b125_1_a
_cod_depositor_comments
'Adding full bibliography for 1573093--1573094.cif.'
_cod_database_code               1573093
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C9(H9), C8(H8), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.5000 0.36023(3) 0.7500 0.06432(18) Uani 1 2 d S T P . .
Cl1 Cl 0.5000 0.51361(12) 0.7500 0.1102(7) Uani 1 2 d S T P . .
N1 N 0.5255(2) 0.1677(2) 0.6688(2) 0.0603(8) Uani 1 1 d . . . . .
C1 C 0.5000 0.2228(4) 0.7500 0.0580(14) Uani 1 2 d S T P . .
C2 C 0.5157(3) 0.0797(3) 0.6987(3) 0.0724(11) Uani 1 1 d . . . . .
H2 H 0.5282 0.0301 0.6563 0.087 Uiso 1 1 calc R U . . .
C3 C 0.5523(3) 0.2005(3) 0.5609(3) 0.0613(10) Uani 1 1 d . . . . .
H3 H 0.5784 0.2611 0.5704 0.074 Uiso 1 1 calc R U . . .
C6 C 0.8041(4) 0.0785(4) 0.5476(6) 0.1174(19) Uani 1 1 d . . . . .
H6 H 0.8588 0.0659 0.5940 0.141 Uiso 1 1 calc R U . . .
C5 C 0.7228(3) 0.1259(3) 0.5832(4) 0.0907(14) Uani 1 1 d . . . . .
H5 H 0.7235 0.1459 0.6540 0.109 Uiso 1 1 calc R U . . .
C4 C 0.6395(3) 0.1450(3) 0.5173(3) 0.0678(10) Uani 1 1 d . . . . .
C9 C 0.6408(3) 0.1162(3) 0.4125(3) 0.0888(14) Uani 1 1 d . . . . .
H9 H 0.5859 0.1285 0.3661 0.107 Uiso 1 1 calc R U . . .
C8 C 0.7251(5) 0.0682(4) 0.3757(5) 0.120(2) Uani 1 1 d . . . . .
H8 H 0.7263 0.0491 0.3047 0.144 Uiso 1 1 calc R U . . .
C7 C 0.8051(5) 0.0497(4) 0.4440(7) 0.125(2) Uani 1 1 d . . . . .
H7 H 0.8605 0.0173 0.4197 0.150 Uiso 1 1 calc R U . . .
C10 C 0.4586(3) 0.2067(3) 0.4876(3) 0.0655(11) Uani 1 1 d . . . . .
C11 C 0.3833(3) 0.1432(3) 0.4834(3) 0.0865(14) Uani 1 1 d . . . . .
H11 H 0.3881 0.0939 0.5283 0.104 Uiso 1 1 calc R U . . .
C12 C 0.3008(4) 0.1516(4) 0.4137(4) 0.1053(17) Uani 1 1 d . . . . .
H12 H 0.2505 0.1079 0.4115 0.126 Uiso 1 1 calc R U . . .
C13 C 0.2925(4) 0.2233(4) 0.3482(4) 0.1047(17) Uani 1 1 d . . . . .
H13 H 0.2365 0.2287 0.3012 0.126 Uiso 1 1 calc R U . . .
C14 C 0.3659(4) 0.2876(4) 0.3511(4) 0.1093(18) Uani 1 1 d . . . . .
H14 H 0.3604 0.3367 0.3059 0.131 Uiso 1 1 calc R U . . .
C15 C 0.4486(3) 0.2795(3) 0.4216(3) 0.0903(15) Uani 1 1 d . . . . .
H15 H 0.4981 0.3238 0.4243 0.108 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ag1 Cl1 180.0 . . ?
C1 N1 C2 111.1(3) . . ?
C1 N1 C3 122.7(3) . . ?
C2 N1 C3 126.1(3) . . ?
N1 C1 Ag1 127.8(2) . . ?
N1 C1 Ag1 127.8(2) 2_656 . ?
N1 C1 N1 104.5(4) 2_656 . ?
N1 C2 H2 126.7 . . ?
C2 C2 N1 106.65(18) 2_656 . ?
C2 C2 H2 126.7 2_656 . ?
N1 C3 H3 106.9 . . ?
N1 C3 C4 109.6(3) . . ?
N1 C3 C10 111.2(3) . . ?
C4 C3 H3 106.9 . . ?
C10 C3 H3 106.9 . . ?
C10 C3 C4 114.9(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.0(6) . . ?
C6 C5 H5 119.1 . . ?
C6 C5 C4 121.8(5) . . ?
C4 C5 H5 119.1 . . ?
C5 C4 C3 119.3(3) . . ?
C9 C4 C3 122.5(4) . . ?
C9 C4 C5 118.1(4) . . ?
C4 C9 H9 120.0 . . ?
C4 C9 C8 119.9(5) . . ?
C8 C9 H9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
C6 C7 C8 120.1(6) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C11 C10 C3 123.4(4) . . ?
C11 C10 C15 118.3(4) . . ?
C15 C10 C3 118.3(4) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.9(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.7(5) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 120.8(4) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 Cl1 2.3065(18) . ?
Ag1 C1 2.066(5) . ?
N1 C1 1.355(4) . ?
N1 C2 1.381(5) . ?
N1 C3 1.480(4) . ?
C1 N1 1.355(4) 2_656 ?
C2 C2 1.351(7) 2_656 ?
C2 H2 0.9300 . ?
C3 H3 0.9800 . ?
C3 C4 1.524(5) . ?
C3 C10 1.515(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.363(7) . ?
C6 C7 1.360(8) . ?
C5 H5 0.9300 . ?
C5 C4 1.380(6) . ?
C4 C9 1.374(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.404(7) . ?
C8 H8 0.9300 . ?
C8 C7 1.362(8) . ?
C7 H7 0.9300 . ?
C10 C11 1.372(5) . ?
C10 C15 1.373(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.354(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.363(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(6) . ?
C15 H15 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 C5 -45.7(5) . . . . ?
N1 C3 C4 C9 137.2(4) . . . . ?
N1 C3 C10 C11 -41.6(5) . . . . ?
N1 C3 C10 C15 138.6(4) . . . . ?
C1 N1 C2 C2 -0.6(5) . . . 2_656 ?
C1 N1 C3 C4 141.3(3) . . . . ?
C1 N1 C3 C10 -90.5(4) . . . . ?
C2 N1 C1 Ag1 -179.8(2) . . . . ?
C2 N1 C1 N1 0.2(2) . . . 2_656 ?
C2 N1 C3 C4 -43.6(5) . . . . ?
C2 N1 C3 C10 84.6(4) . . . . ?
C3 N1 C1 Ag1 -4.0(3) . . . . ?
C3 N1 C1 N1 176.0(3) . . . 2_656 ?
C3 N1 C2 C2 -176.2(4) . . . 2_656 ?
C3 C4 C9 C8 177.6(4) . . . . ?
C3 C10 C11 C12 -178.8(4) . . . . ?
C3 C10 C15 C14 178.5(4) . . . . ?
C6 C5 C4 C3 -178.3(4) . . . . ?
C6 C5 C4 C9 -1.1(7) . . . . ?
C5 C6 C7 C8 0.1(9) . . . . ?
C5 C4 C9 C8 0.5(6) . . . . ?
C4 C3 C10 C11 83.7(4) . . . . ?
C4 C3 C10 C15 -96.1(5) . . . . ?
C4 C9 C8 C7 0.5(8) . . . . ?
C9 C8 C7 C6 -0.8(9) . . . . ?
C7 C6 C5 C4 0.8(8) . . . . ?
C10 C3 C4 C5 -171.8(4) . . . . ?
C10 C3 C4 C9 11.1(5) . . . . ?
C10 C11 C12 C13 -0.3(8) . . . . ?
C11 C10 C15 C14 -1.3(7) . . . . ?
C11 C12 C13 C14 0.0(8) . . . . ?
C12 C13 C14 C15 -0.3(9) . . . . ?
C13 C14 C15 C10 1.0(8) . . . . ?
C15 C10 C11 C12 1.0(7) . . . . ?
