#------------------------------------------------------------------------------
#$Date: 2019-11-25 22:21:52 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/18/4131806.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_4131806
loop_
_publ_author_name
'Hansmann, Max M.'
'Melaimi, Mohand'
'Munz, Dominik'
'Bertrand, Guy'
_publ_section_title
;
 Modular Approach to Kekulé Diradicaloids Derived from Cyclic
 (Alkyl)(amino)carbenes.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2546
_journal_page_last               2554
_journal_paper_doi               10.1021/jacs.7b11183
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         '2(F6 Sb), C54 H74 N2'
_chemical_formula_sum            'C54 H74 F12 N2 Sb2'
_chemical_formula_weight         1222.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-08-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.598(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.2342(9)
_cell_length_b                   9.4798(7)
_cell_length_c                   23.3954(16)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.71
_cell_measurement_theta_min      2.33
_cell_volume                     3237.9(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            30082
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         1.395
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  0.2594
_exptl_absorpt_correction_T_min  0.2276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0893 before and 0.0378 after correction. The Ratio of minimum to maximum transmission is 0.8774. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             1244
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.011
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5934
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0398
_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)+(0.0396P)²+4.2942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4468
_reflns_number_total             5934
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            4aEt.cif
_cod_data_source_block           gb_mm95_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4131806
_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.
;
_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. Restrained distances
 C4-C22A \\sim C4-C22 \\sim C22-C21 \\sim C22A-C21A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C22A) = Uanis(C22)
4. Others
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
5.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C3(H3A,H3B), C22(H22A,H22B), C22A(H22C,H22D)
5.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C26(H26), C8(H8), C9(H9), C7(H7)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C21(H21A,
 H21B,H21C), C21A(H21D,H21E,H21F)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.24858(2) -0.24615(3) 0.24848(2) 0.04047(10) Uani 1 1 d . . . .
F5 F 0.18158(12) -0.4038(2) 0.21240(8) 0.0391(4) Uani 1 1 d . . . .
F1 F 0.18148(16) -0.1341(2) 0.18549(10) 0.0631(6) Uani 1 1 d . . . .
N1 N 0.14133(15) 0.1570(3) 0.42374(10) 0.0252(5) Uani 1 1 d . . . .
F2 F 0.15961(17) -0.2099(3) 0.28796(11) 0.0715(7) Uani 1 1 d . . . .
F4 F 0.33557(15) -0.2821(3) 0.20835(13) 0.0767(8) Uani 1 1 d . . . .
F3 F 0.31489(16) -0.0896(3) 0.28533(12) 0.0834(8) Uani 1 1 d . . . .
C1 C 0.17976(18) 0.2396(3) 0.39430(13) 0.0260(6) Uani 1 1 d . . . .
F6 F 0.31120(19) -0.3610(3) 0.31206(11) 0.0954(10) Uani 1 1 d . . . .
C5 C 0.18471(19) 0.1138(3) 0.48556(12) 0.0286(7) Uani 1 1 d . . . .
C4 C 0.12638(19) 0.2603(3) 0.33015(13) 0.0282(7) Uani 1 1 d D . . .
C6 C 0.17258(19) 0.1980(3) 0.53207(13) 0.0302(7) Uani 1 1 d . . . .
C2 C 0.04595(19) 0.1084(3) 0.38718(13) 0.0306(7) Uani 1 1 d . . . .
C19 C 0.1169(2) 0.4175(3) 0.31415(13) 0.0316(7) Uani 1 1 d . . . .
H19A H 0.1784 0.4553 0.3166 0.038 Uiso 1 1 calc R . . .
H19B H 0.0789 0.4268 0.2722 0.038 Uiso 1 1 calc R . . .
C10 C 0.2391(2) -0.0076(4) 0.49503(13) 0.0351(7) Uani 1 1 d . . . .
C23 C 0.2657(2) 0.3025(3) 0.42096(14) 0.0310(7) Uani 1 1 d . . . .
C11 C 0.1286(2) 0.3425(4) 0.52390(14) 0.0350(7) Uani 1 1 d . . . .
H11 H 0.1021 0.3597 0.4802 0.042 Uiso 1 1 calc R . . .
C24 C 0.3357(2) 0.3626(3) 0.44218(14) 0.0334(7) Uani 1 1 d . . . .
C3 C 0.0346(2) 0.1884(4) 0.32805(13) 0.0347(7) Uani 1 1 d . . . .
H3A H 0.0171 0.1217 0.2941 0.042 Uiso 1 1 calc R . . .
H3B H -0.0142 0.2602 0.3226 0.042 Uiso 1 1 calc R . . .
C25 C 0.41956(18) 0.4329(3) 0.47110(14) 0.0307(7) Uani 1 1 d . . . .
C27 C 0.5353(2) 0.6030(4) 0.47049(15) 0.0377(8) Uani 1 1 d . . . .
H27 H 0.5598 0.6734 0.4505 0.045 Uiso 1 1 calc R . . .
C26 C 0.4546(2) 0.5361(4) 0.44154(15) 0.0375(8) Uani 1 1 d . . . .
H26 H 0.4230 0.5604 0.4016 0.045 Uiso 1 1 calc R . . .
C8 C 0.2601(2) 0.0255(4) 0.60058(15) 0.0457(9) Uani 1 1 d . . . .
H8 H 0.2837 -0.0075 0.6404 0.055 Uiso 1 1 calc R . . .
C14 C 0.2674(2) -0.0870(4) 0.44621(15) 0.0391(8) Uani 1 1 d . . . .
H14 H 0.2299 -0.0503 0.4067 0.047 Uiso 1 1 calc R . . .
C9 C 0.2747(2) -0.0513(4) 0.55424(15) 0.0430(8) Uani 1 1 d . . . .
H9 H 0.3098 -0.1356 0.5626 0.052 Uiso 1 1 calc R . . .
C18 C 0.0448(2) -0.0504(4) 0.37948(15) 0.0426(8) Uani 1 1 d . . . .
H18A H 0.0870 -0.0770 0.3566 0.064 Uiso 1 1 calc GR . . .
H18B H -0.0173 -0.0812 0.3581 0.064 Uiso 1 1 calc GR . . .
H18C H 0.0639 -0.0957 0.4187 0.064 Uiso 1 1 calc GR . . .
C7 C 0.2119(2) 0.1488(4) 0.58983(14) 0.0409(8) Uani 1 1 d . . . .
H7 H 0.2051 0.2025 0.6226 0.049 Uiso 1 1 calc R . . .
C20 C 0.0750(2) 0.5073(4) 0.35289(15) 0.0423(8) Uani 1 1 d . . . .
H20A H 0.0731 0.6059 0.3400 0.063 Uiso 1 1 calc GR . . .
H20B H 0.1121 0.4997 0.3946 0.063 Uiso 1 1 calc GR . . .
H20C H 0.0126 0.4744 0.3492 0.063 Uiso 1 1 calc GR . . .
C12 C 0.1998(2) 0.4581(4) 0.54924(16) 0.0460(9) Uani 1 1 d . . . .
H12A H 0.2238 0.4467 0.5925 0.069 Uiso 1 1 calc GR . . .
H12B H 0.1709 0.5510 0.5402 0.069 Uiso 1 1 calc GR . . .
H12C H 0.2501 0.4504 0.5311 0.069 Uiso 1 1 calc GR . . .
C13 C 0.0510(2) 0.3542(4) 0.55352(15) 0.0456(9) Uani 1 1 d . . . .
H13A H 0.0030 0.2855 0.5355 0.068 Uiso 1 1 calc GR . . .
H13B H 0.0252 0.4496 0.5477 0.068 Uiso 1 1 calc GR . . .
H13C H 0.0752 0.3350 0.5963 0.068 Uiso 1 1 calc GR . . .
C17 C -0.0235(2) 0.1528(4) 0.41895(14) 0.0410(8) Uani 1 1 d . . . .
H17A H -0.0075 0.1103 0.4588 0.062 Uiso 1 1 calc GR . . .
H17B H -0.0846 0.1211 0.3960 0.062 Uiso 1 1 calc GR . . .
H17C H -0.0232 0.2558 0.4226 0.062 Uiso 1 1 calc GR . . .
C22 C 0.1860(4) 0.1818(6) 0.29633(19) 0.0360(13) Uani 0.766(7) 1 d D P A 1
H22A H 0.2497 0.2172 0.3103 0.043 Uiso 0.766(7) 1 calc R P A 1
H22B H 0.1870 0.0798 0.3057 0.043 Uiso 0.766(7) 1 calc R P A 1
C16 C 0.2500(3) -0.2457(3) 0.44811(18) 0.0493(9) Uani 1 1 d . . . .
H16A H 0.2903 -0.2854 0.4850 0.074 Uiso 1 1 calc GR . . .
H16B H 0.2627 -0.2913 0.4137 0.074 Uiso 1 1 calc GR . . .
H16C H 0.1860 -0.2621 0.4469 0.074 Uiso 1 1 calc GR . . .
C15 C 0.3680(2) -0.0583(4) 0.45182(18) 0.0527(10) Uani 1 1 d . . . .
H15A H 0.3780 0.0437 0.4507 0.079 Uiso 1 1 calc GR . . .
H15B H 0.3846 -0.1035 0.4187 0.079 Uiso 1 1 calc GR . . .
H15C H 0.4062 -0.0966 0.4897 0.079 Uiso 1 1 calc GR . . .
C21 C 0.1499(3) 0.2020(5) 0.22910(17) 0.0454(14) Uani 0.766(7) 1 d D P A 1
H21A H 0.1818 0.1374 0.2091 0.068 Uiso 0.766(7) 1 calc GR P A 1
H21B H 0.1607 0.2995 0.2189 0.068 Uiso 0.766(7) 1 calc GR P A 1
H21C H 0.0841 0.1822 0.2160 0.068 Uiso 0.766(7) 1 calc GR P A 1
C22A C 0.1546(10) 0.182(2) 0.2800(7) 0.0360(13) Uani 0.234(7) 1 d D P A 2
H22C H 0.1577 0.0799 0.2888 0.043 Uiso 0.234(7) 1 calc R P A 2
H22D H 0.1059 0.1965 0.2420 0.043 Uiso 0.234(7) 1 calc R P A 2
C21A C 0.2463(8) 0.2284(15) 0.2711(6) 0.034(4) Uani 0.234(7) 1 d D P A 2
H21D H 0.2588 0.1726 0.2390 0.051 Uiso 0.234(7) 1 calc GR P A 2
H21E H 0.2954 0.2136 0.3081 0.051 Uiso 0.234(7) 1 calc GR P A 2
H21F H 0.2433 0.3286 0.2604 0.051 Uiso 0.234(7) 1 calc GR P A 2
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'
Sb Sb -0.5866 1.5461 '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
F5 Sb1 F2 89.47(10) . .
F5 Sb1 F6 88.99(11) . .
F1 Sb1 F5 89.61(9) . .
F1 Sb1 F2 88.55(11) . .
F1 Sb1 F6 177.61(11) . .
F4 Sb1 F5 90.07(9) . .
F4 Sb1 F1 90.82(12) . .
F4 Sb1 F2 179.22(10) . .
F4 Sb1 F3 90.54(11) . .
F4 Sb1 F6 91.12(14) . .
F3 Sb1 F5 179.24(10) . .
F3 Sb1 F1 90.83(12) . .
F3 Sb1 F2 89.92(11) . .
F3 Sb1 F6 90.55(13) . .
F6 Sb1 F2 89.50(13) . .
C1 N1 C5 123.5(2) . .
C1 N1 C2 112.8(2) . .
C5 N1 C2 123.7(2) . .
N1 C1 C4 114.5(2) . .
N1 C1 C23 121.7(3) . .
C23 C1 C4 123.8(3) . .
C6 C5 N1 118.9(3) . .
C10 C5 N1 117.8(3) . .
C10 C5 C6 123.2(3) . .
C1 C4 C19 110.9(2) . .
C1 C4 C3 101.6(2) . .
C1 C4 C22 102.6(3) . .
C1 C4 C22A 120.5(8) . .
C19 C4 C3 113.6(3) . .
C19 C4 C22 111.7(3) . .
C19 C4 C22A 107.9(9) . .
C3 C4 C22 115.3(3) . .
C3 C4 C22A 102.1(6) . .
C5 C6 C11 124.6(3) . .
C7 C6 C5 116.5(3) . .
C7 C6 C11 118.5(3) . .
N1 C2 C3 101.4(2) . .
C18 C2 N1 110.0(3) . .
C18 C2 C3 112.8(3) . .
C18 C2 C17 110.4(3) . .
C17 C2 N1 109.0(2) . .
C17 C2 C3 112.8(3) . .
C20 C19 C4 115.3(3) . .
C5 C10 C14 124.6(3) . .
C9 C10 C5 116.4(3) . .
C9 C10 C14 118.8(3) . .
C24 C23 C1 176.2(4) . .
C6 C11 C12 111.0(3) . .
C6 C11 C13 112.3(3) . .
C13 C11 C12 108.9(3) . .
C23 C24 C25 176.7(3) . .
C4 C3 C2 108.7(2) . .
C27 C25 C24 118.5(3) 3_666 .
C27 C25 C26 120.7(3) 3_666 .
C26 C25 C24 120.8(3) . .
C26 C27 C25 119.6(3) . 3_666
C27 C26 C25 119.7(3) . .
C7 C8 C9 120.5(3) . .
C10 C14 C16 112.0(3) . .
C15 C14 C10 109.8(3) . .
C15 C14 C16 110.5(3) . .
C8 C9 C10 121.3(3) . .
C8 C7 C6 121.7(3) . .
C21 C22 C4 112.0(4) . .
C21A C22A C4 115.3(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sb1 F5 1.8698(18) .
Sb1 F1 1.867(2) .
Sb1 F2 1.877(2) .
Sb1 F4 1.861(2) .
Sb1 F3 1.862(2) .
Sb1 F6 1.870(3) .
N1 C1 1.289(4) .
N1 C5 1.466(4) .
N1 C2 1.531(3) .
C1 C4 1.502(4) .
C1 C23 1.411(4) .
C5 C6 1.404(4) .
C5 C10 1.398(4) .
C4 C19 1.533(4) .
C4 C3 1.543(4) .
C4 C22 1.554(5) .
C4 C22A 1.549(8) .
C6 C11 1.513(5) .
C6 C7 1.393(4) .
C2 C3 1.543(4) .
C2 C18 1.515(5) .
C2 C17 1.515(4) .
C19 C20 1.511(4) .
C10 C14 1.529(5) .
C10 C9 1.398(4) .
C23 C24 1.185(4) .
C11 C12 1.537(5) .
C11 C13 1.536(4) .
C24 C25 1.429(4) .
C25 C27 1.385(4) 3_666
C25 C26 1.389(4) .
C27 C25 1.386(4) 3_666
C27 C26 1.378(4) .
C8 C9 1.376(5) .
C8 C7 1.365(5) .
C14 C16 1.530(5) .
C14 C15 1.525(5) .
C22 C21 1.523(5) .
C22A C21A 1.535(8) .
