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#$Date: 2024-03-04 21:50:56 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290093 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/25/7132505.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_7132505
loop_
_publ_author_name
'Nayak, Mithilesh Kumar'
'Elvers, Benedict J.'
'Mehta, Sakshi'
'Krummenacher, Ivo'
'Mondal, Abhishake'
'Braunschweig, Holger'
'Schulzke, Carola'
'Ravat, Prince'
'Jana, Anukul'
_publ_section_title
;
 Bis-[cyclic(alkyl)(amino)carbene]-derived diradicals.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1739
_journal_page_last               1742
_journal_paper_doi               10.1039/d3cc05779h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C22 H40 N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H40 F6 N2 O6 S2'
_chemical_formula_weight         630.70
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-07-11 deposited with the CCDC.	2023-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.830(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.6531(9)
_cell_length_b                   10.6359(4)
_cell_length_c                   13.5057(5)
_cell_measurement_reflns_used    7875
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.6940
_cell_measurement_theta_min      2.9180
_cell_volume                     2999.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'XP Version 5.1 by Bruker AXS 1998'
_computing_publication_material  'CIFTAB (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2016 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20113
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.923
_diffrn_reflns_theta_min         2.922
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0477
_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/[σ²(Fo²)+(0.0445P)²+6.4143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2883
_reflns_number_total             3602
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc05779h2.cif
_cod_data_source_block           AJ0698
_cod_depositor_comments
'Adding full bibliography for 7132505--7132514.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7132505
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.967
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
N1 N 0.61395(7) 0.30459(16) 0.70576(13) 0.0229(3) Uani 1 1 d . . . . .
C1 C 0.56601(9) 0.30795(19) 0.75653(15) 0.0230(4) Uani 1 1 d . . . . .
H1 H 0.589461 0.307186 0.836348 0.028 Uiso 1 1 calc R U . . .
C2 C 0.52538(9) 0.42708(19) 0.72503(15) 0.0244(4) Uani 1 1 d . . . . .
H2A H 0.503872 0.431896 0.645812 0.029 Uiso 1 1 calc R U . . .
H2B H 0.553294 0.501794 0.750220 0.029 Uiso 1 1 calc R U . . .
C3 C 0.52438(9) 0.19005(19) 0.72346(17) 0.0268(4) Uani 1 1 d . . . . .
H3A H 0.551728 0.114227 0.745751 0.032 Uiso 1 1 calc R U . . .
H3B H 0.501649 0.187990 0.644353 0.032 Uiso 1 1 calc R U . . .
C4 C 0.68514(9) 0.2834(2) 0.77023(16) 0.0254(4) Uani 1 1 d . . . . .
C5 C 0.71147(9) 0.2974(2) 0.68110(16) 0.0293(4) Uani 1 1 d . . . . .
H5A H 0.743525 0.231087 0.688247 0.035 Uiso 1 1 calc R U . . .
H5B H 0.732318 0.380399 0.686535 0.035 Uiso 1 1 calc R U . . .
C6 C 0.65416(9) 0.2852(2) 0.57198(16) 0.0269(4) Uani 1 1 d . . . . .
C7 C 0.59920(9) 0.3095(2) 0.60471(16) 0.0273(4) Uani 1 1 d . . . . .
C8 C 0.71024(10) 0.3846(2) 0.85590(17) 0.0309(5) Uani 1 1 d . . . . .
H8A H 0.697157 0.467449 0.822964 0.046 Uiso 1 1 calc R U . . .
H8B H 0.757090 0.380191 0.889070 0.046 Uiso 1 1 calc R U . . .
H8C H 0.692652 0.371315 0.910919 0.046 Uiso 1 1 calc R U . . .
C9 C 0.69470(10) 0.1545(2) 0.82219(18) 0.0313(5) Uani 1 1 d . . . . .
H9A H 0.672825 0.150997 0.872097 0.047 Uiso 1 1 calc R U . . .
H9B H 0.740566 0.139098 0.861532 0.047 Uiso 1 1 calc R U . . .
H9C H 0.676888 0.090234 0.766522 0.047 Uiso 1 1 calc R U . . .
C10 C 0.65640(12) 0.3815(2) 0.48937(19) 0.0380(5) Uani 1 1 d . . . . .
H10A H 0.616934 0.375925 0.424640 0.057 Uiso 1 1 calc R U . . .
H10B H 0.693307 0.364003 0.470734 0.057 Uiso 1 1 calc R U . . .
H10C H 0.660378 0.466203 0.519813 0.057 Uiso 1 1 calc R U . . .
C11 C 0.64567(12) 0.1528(2) 0.52339(19) 0.0384(5) Uani 1 1 d . . . . .
H11A H 0.645302 0.091189 0.577069 0.058 Uiso 1 1 calc R U . . .
H11B H 0.681191 0.134291 0.501377 0.058 Uiso 1 1 calc R U . . .
H11C H 0.605095 0.148469 0.460667 0.058 Uiso 1 1 calc R U . . .
H7 H 0.5548(11) 0.318(2) 0.5537(18) 0.029(6) Uiso 1 1 d . . . . .
S1 S 0.39475(2) 0.30753(5) 0.40375(4) 0.02440(14) Uani 1 1 d . . . . .
O1 O 0.34954(8) 0.37562(16) 0.31514(13) 0.0425(4) Uani 1 1 d . . . . .
O2 O 0.36792(9) 0.2428(2) 0.46935(14) 0.0485(5) Uani 1 1 d . . . . .
O3 O 0.45345(7) 0.37409(16) 0.46171(12) 0.0383(4) Uani 1 1 d . . . . .
C12 C 0.42086(12) 0.1824(2) 0.3398(2) 0.0426(6) Uani 1 1 d . . . . .
F1 F 0.44834(10) 0.2273(2) 0.27670(17) 0.0779(6) Uani 1 1 d . . . . .
F2 F 0.37216(9) 0.11132(17) 0.27922(18) 0.0796(6) Uani 1 1 d . . . . .
F3 F 0.46305(9) 0.10725(17) 0.41234(18) 0.0792(6) Uani 1 1 d . . . . .
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C7 N1 C1 123.77(16) . . ?
C7 N1 C4 113.45(16) . . ?
C1 N1 C4 122.58(15) . . ?
N1 C1 C2 111.06(15) . . ?
N1 C1 C3 108.82(15) . . ?
C2 C1 C3 111.28(15) . . ?
C1 C2 C2 110.44(13) . 2_656 ?
C1 C3 C3 109.77(14) . 2_656 ?
C9 C4 C8 110.09(17) . . ?
C9 C4 N1 109.13(16) . . ?
C8 C4 N1 109.33(16) . . ?
C9 C4 C5 114.77(18) . . ?
C8 C4 C5 112.43(17) . . ?
N1 C4 C5 100.58(14) . . ?
C4 C5 C6 107.42(15) . . ?
C7 C6 C10 111.49(18) . . ?
C7 C6 C11 107.75(18) . . ?
C10 C6 C11 109.67(18) . . ?
C7 C6 C5 101.01(16) . . ?
C10 C6 C5 112.68(18) . . ?
C11 C6 C5 113.88(18) . . ?
N1 C7 C6 114.02(17) . . ?
O2 S1 O1 115.00(11) . . ?
O2 S1 O3 115.11(10) . . ?
O1 S1 O3 114.54(10) . . ?
O2 S1 C12 103.81(12) . . ?
O1 S1 C12 103.48(12) . . ?
O3 S1 C12 102.55(11) . . ?
F1 C12 F2 107.2(2) . . ?
F1 C12 F3 107.9(2) . . ?
F2 C12 F3 107.3(2) . . ?
F1 C12 S1 111.42(19) . . ?
F2 C12 S1 111.50(18) . . ?
F3 C12 S1 111.31(18) . . ?
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
N1 C7 1.274(3) . ?
N1 C1 1.493(2) . ?
N1 C4 1.523(2) . ?
C1 C2 1.526(3) . ?
C1 C3 1.528(3) . ?
C2 C2 1.542(4) 2_656 ?
C3 C3 1.533(4) 2_656 ?
C4 C9 1.517(3) . ?
C4 C8 1.520(3) . ?
C4 C5 1.544(3) . ?
C5 C6 1.546(3) . ?
C6 C7 1.496(3) . ?
C6 C10 1.530(3) . ?
C6 C11 1.533(3) . ?
S1 O2 1.4302(17) . ?
S1 O1 1.4333(16) . ?
S1 O3 1.4404(15) . ?
S1 C12 1.807(2) . ?
C12 F1 1.324(3) . ?
C12 F2 1.326(3) . ?
C12 F3 1.337(3) . ?
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
C7 N1 C1 C2 -57.9(3) . . . . ?
C4 N1 C1 C2 127.51(18) . . . . ?
C7 N1 C1 C3 64.9(2) . . . . ?
C4 N1 C1 C3 -109.67(19) . . . . ?
N1 C1 C2 C2 178.10(17) . . . 2_656 ?
C3 C1 C2 C2 56.7(2) . . . 2_656 ?
N1 C1 C3 C3 178.84(17) . . . 2_656 ?
C2 C1 C3 C3 -58.5(2) . . . 2_656 ?
C7 N1 C4 C9 -112.6(2) . . . . ?
C1 N1 C4 C9 62.4(2) . . . . ?
C7 N1 C4 C8 126.90(19) . . . . ?
C1 N1 C4 C8 -58.0(2) . . . . ?
C7 N1 C4 C5 8.4(2) . . . . ?
C1 N1 C4 C5 -176.52(17) . . . . ?
C9 C4 C5 C6 100.4(2) . . . . ?
C8 C4 C5 C6 -132.78(18) . . . . ?
N1 C4 C5 C6 -16.6(2) . . . . ?
C4 C5 C6 C7 18.5(2) . . . . ?
C4 C5 C6 C10 137.58(18) . . . . ?
C4 C5 C6 C11 -96.7(2) . . . . ?
C1 N1 C7 C6 -171.23(18) . . . . ?
C4 N1 C7 C6 3.8(3) . . . . ?
C10 C6 C7 N1 -134.0(2) . . . . ?
C11 C6 C7 N1 105.6(2) . . . . ?
C5 C6 C7 N1 -14.1(2) . . . . ?
O2 S1 C12 F1 -178.83(19) . . . . ?
O1 S1 C12 F1 60.7(2) . . . . ?
O3 S1 C12 F1 -58.7(2) . . . . ?
O2 S1 C12 F2 61.4(2) . . . . ?
O1 S1 C12 F2 -59.0(2) . . . . ?
O3 S1 C12 F2 -178.39(19) . . . . ?
O2 S1 C12 F3 -58.4(2) . . . . ?
O1 S1 C12 F3 -178.83(18) . . . . ?
O3 S1 C12 F3 61.8(2) . . . . ?
