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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/7/13/25/7132507.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_7132507
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         'C26 H46 N2 S2'
_chemical_formula_sum            'C26 H46 N2 S2'
_chemical_formula_weight         450.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2275(10)
_cell_length_b                   7.8196(6)
_cell_length_c                   27.4908(19)
_cell_measurement_reflns_used    4417
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.5160
_cell_measurement_theta_min      3.1740
_cell_volume                     2628.5(3)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.930
_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  0.0473
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            17331
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.939
_diffrn_reflns_theta_min         2.964
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45475
_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    1.139
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         1688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0443
_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)+(0.0538P)²+1.4602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1275
_reflns_number_total             1688
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc05779h2.cif
_cod_data_source_block           AJ1386
_cod_depositor_comments
'Adding full bibliography for 7132505--7132514.cif.'
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_original_sg_symbol_H-M      'C m c a'
_cod_database_code               7132507
_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   0.948
_shelx_estimated_absorpt_t_max   0.964
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'
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
S1 S 0.500000 0.61665(7) 0.63542(2) 0.0525(2) Uani 1 2 d S T P . .
N1 N 0.500000 0.3112(2) 0.58999(6) 0.0310(4) Uani 1 2 d S T P . .
C1 C 0.500000 0.3757(3) 0.53953(7) 0.0344(5) Uani 1 2 d S T P . .
H1 H 0.500000 0.274695 0.518405 0.041 Uiso 1 2 calc R U P . .
C2 C 0.60374(12) 0.4763(2) 0.52711(5) 0.0406(4) Uani 1 1 d . . . . .
H2A H 0.667687 0.407595 0.534498 0.049 Uiso 1 1 calc R U . . .
H2B H 0.606911 0.579393 0.546669 0.049 Uiso 1 1 calc R U . . .
C3 C 0.500000 0.4047(3) 0.63042(7) 0.0334(5) Uani 1 2 d S T P . .
C4 C 0.500000 0.2885(3) 0.67507(7) 0.0347(5) Uani 1 2 d S T P . .
C5 C 0.500000 0.1059(3) 0.65364(8) 0.0374(5) Uani 1 2 d S T P . .
H5A H 0.564355 0.044063 0.664448 0.045 Uiso 0.5 1 calc R U P . .
H5B H 0.435645 0.044063 0.664448 0.045 Uiso 0.5 1 calc R U P . .
C6 C 0.500000 0.1211(3) 0.59786(8) 0.0371(5) Uani 1 2 d S T P . .
C7 C 0.39738(17) 0.0426(2) 0.57564(6) 0.0559(5) Uani 1 1 d . . . . .
H7A H 0.333836 0.096614 0.589237 0.084 Uiso 1 1 calc R U . . .
H7B H 0.395515 -0.077604 0.582637 0.084 Uiso 1 1 calc R U . . .
H7C H 0.398164 0.059513 0.541051 0.084 Uiso 1 1 calc R U . . .
C8 C 0.60225(16) 0.3254(3) 0.70626(6) 0.0522(5) Uani 1 1 d . . . . .
H8A H 0.596626 0.441013 0.718799 0.063 Uiso 1 1 calc R U . . .
H8B H 0.601726 0.248416 0.733922 0.063 Uiso 1 1 calc R U . . .
C9 C 0.71104(16) 0.3076(3) 0.68061(8) 0.0666(6) Uani 1 1 d . . . . .
H9A H 0.710297 0.374144 0.651270 0.100 Uiso 1 1 calc R U . . .
H9B H 0.723482 0.189544 0.672727 0.100 Uiso 1 1 calc R U . . .
H9C H 0.768424 0.347644 0.701536 0.100 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'
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
C3 N1 C1 126.71(18) . . ?
C3 N1 C6 115.05(16) . . ?
C1 N1 C6 118.24(16) . . ?
N1 C1 C2 112.63(11) . . ?
N1 C1 C2 112.63(11) . 12_655 ?
C2 C1 C2 111.88(17) . 12_655 ?
N1 C1 H1 106.4 . . ?
C2 C1 H1 106.4 . . ?
C2 C1 H1 106.4 12_655 . ?
C1 C2 C2 109.90(12) . 4_566 ?
C1 C2 H2A 109.7 . . ?
C2 C2 H2A 109.7 4_566 . ?
C1 C2 H2B 109.7 . . ?
C2 C2 H2B 109.7 4_566 . ?
H2A C2 H2B 108.2 . . ?
N1 C3 C4 110.17(18) . . ?
N1 C3 S1 128.06(16) . . ?
C4 C3 S1 121.77(15) . . ?
C3 C4 C8 109.59(12) . 12_655 ?
C3 C4 C8 109.59(12) . . ?
C8 C4 C8 108.24(19) 12_655 . ?
C3 C4 C5 104.09(16) . . ?
C8 C4 C5 112.62(12) 12_655 . ?
C8 C4 C5 112.62(12) . . ?
C6 C5 C4 107.98(16) . . ?
C6 C5 H5A 110.1 . . ?
C4 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
C4 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
N1 C6 C7 109.91(12) . 12_655 ?
N1 C6 C7 109.91(12) . . ?
C7 C6 C7 110.8(2) 12_655 . ?
N1 C6 C5 102.71(16) . . ?
C7 C6 C5 111.62(12) 12_655 . ?
C7 C6 C5 111.61(12) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C4 115.88(14) . . ?
C9 C8 H8A 108.3 . . ?
C4 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C4 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
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
S1 C3 1.663(2) . ?
N1 C3 1.330(3) . ?
N1 C1 1.476(2) . ?
N1 C6 1.503(3) . ?
C1 C2 1.5311(19) . ?
C1 C2 1.5311(19) 12_655 ?
C1 H1 0.9800 . ?
C2 C2 1.536(3) 4_566 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.527(3) . ?
C4 C8 1.543(2) 12_655 ?
C4 C8 1.543(2) . ?
C4 C5 1.545(3) . ?
C5 C6 1.538(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.524(2) 12_655 ?
C6 C7 1.524(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.512(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2B S1 0.97 2.78 3.4175(17) 123.6 . yes
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
C3 N1 C1 C2 63.84(14) . . . . ?
C6 N1 C1 C2 -116.16(14) . . . . ?
C3 N1 C1 C2 -63.84(14) . . . 12_655 ?
C6 N1 C1 C2 116.16(14) . . . 12_655 ?
N1 C1 C2 C2 174.30(17) . . . 4_566 ?
C2 C1 C2 C2 -57.6(3) 12_655 . . 4_566 ?
C1 N1 C3 C4 180.000(1) . . . . ?
C6 N1 C3 C4 0.000(1) . . . . ?
C1 N1 C3 S1 0.000(1) . . . . ?
C6 N1 C3 S1 180.000(1) . . . . ?
N1 C3 C4 C8 -120.68(13) . . . 12_655 ?
S1 C3 C4 C8 59.32(13) . . . 12_655 ?
N1 C3 C4 C8 120.68(13) . . . . ?
S1 C3 C4 C8 -59.32(13) . . . . ?
N1 C3 C4 C5 0.000(1) . . . . ?
S1 C3 C4 C5 180.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C8 C4 C5 C6 118.63(12) 12_655 . . . ?
C8 C4 C5 C6 -118.63(12) . . . . ?
C3 N1 C6 C7 -118.90(13) . . . 12_655 ?
C1 N1 C6 C7 61.10(13) . . . 12_655 ?
C3 N1 C6 C7 118.90(13) . . . . ?
C1 N1 C6 C7 -61.10(13) . . . . ?
C3 N1 C6 C5 0.000(1) . . . . ?
C1 N1 C6 C5 180.000(1) . . . . ?
C4 C5 C6 N1 0.000(1) . . . . ?
C4 C5 C6 C7 117.70(14) . . . 12_655 ?
C4 C5 C6 C7 -117.70(14) . . . . ?
C3 C4 C8 C9 -56.6(2) . . . . ?
C8 C4 C8 C9 -176.10(12) 12_655 . . . ?
C5 C4 C8 C9 58.7(2) . . . . ?
