#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:35:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180228 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/14/7111440.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111440
loop_
_publ_author_name
'Gudat, Dietrich'
'Gans-Eichler, Timo'
'Nieger, Martin'
_publ_section_title
;
 Synthesis and unprecedented oxidation of a cationic Sb-analogue of an
 Arduengo's carbene
;
_journal_issue                   21
_journal_name_full               'Chemical Communications'
_journal_page_first              2434
_journal_page_last               2435
_journal_paper_doi               10.1039/b409657f
_journal_year                    2004
_chemical_formula_moiety         'C10 H20 Cl3 N2 Sb - Sb Cl3'
_chemical_formula_sum            'C10 H20 Cl6 N2 Sb2'
_chemical_formula_weight         624.48
_chemical_name_common
;N,N'-Di-tert.butyl-diazadiene antimopny trichloride, antimony
trichloride adduct
;
_chemical_name_systematic
;
N,N'-Di-tert.butyl-diazadiene antimopny trichloride, antimony
trichloride adduct
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.081(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.0617(1)
_cell_length_b                   17.4255(2)
_cell_length_c                   19.3913(2)
_cell_measurement_reflns_used    4678
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     3985.42(7)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       Collect
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 1 deg.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34881
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    3.508
_exptl_absorpt_correction_T_max  0.7920
_exptl_absorpt_correction_T_min  0.5753
_exptl_absorpt_correction_type   'empirical from multiple refl.'
_exptl_absorpt_process_details   'MULABS (Platon, cf. Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.082
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             2384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0182
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0155P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0391
_refine_ls_wR_factor_ref         0.0406
_reflns_number_gt                2913
_reflns_number_total             3512
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b409657fsup1.cif
_cod_data_source_block           gudat57m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7111440
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Sb1 Sb 0.530209(15) 0.234730(10) 0.604214(9) 0.01759(6) Uani 1 1 d .
Cl1 Cl 0.55971(6) 0.22373(4) 0.48683(3) 0.02507(17) Uani 1 1 d .
Cl2 Cl 0.38651(6) 0.33941(4) 0.55803(3) 0.02583(17) Uani 1 1 d .
Cl3 Cl 0.36523(6) 0.13794(4) 0.56569(4) 0.02803(17) Uani 1 1 d .
N1 N 0.69539(18) 0.14855(12) 0.62711(10) 0.0161(5) Uani 1 1 d .
C11 C 0.6908(2) 0.06288(14) 0.63700(13) 0.0197(6) Uani 1 1 d .
C12 C 0.8079(2) 0.02615(15) 0.65629(14) 0.0257(7) Uani 1 1 d .
H12A H 0.8507 0.0493 0.6998 0.038 Uiso 1 1 calc R
H12B H 0.8483 0.0346 0.6181 0.038 Uiso 1 1 calc R
H12C H 0.7998 -0.0291 0.6634 0.038 Uiso 1 1 calc R
C13 C 0.6261(2) 0.05181(15) 0.69691(13) 0.0248(7) Uani 1 1 d .
H13A H 0.6701 0.0741 0.7405 0.037 Uiso 1 1 calc R
H13B H 0.6148 -0.0031 0.7039 0.037 Uiso 1 1 calc R
H13C H 0.5523 0.0774 0.6844 0.037 Uiso 1 1 calc R
C14 C 0.6238(2) 0.02830(15) 0.56856(13) 0.0241(7) Uani 1 1 d .
H14A H 0.5491 0.0527 0.5562 0.036 Uiso 1 1 calc R
H14B H 0.6144 -0.0270 0.5749 0.036 Uiso 1 1 calc R
H14C H 0.6648 0.0369 0.5306 0.036 Uiso 1 1 calc R
C1 C 0.7887(2) 0.18558(15) 0.64267(12) 0.0190(6) Uani 1 1 d .
H1 H 0.8575 0.1581 0.6577 0.023 Uiso 1 1 calc R
C2 C 0.7923(2) 0.26979(14) 0.63784(12) 0.0173(6) Uani 1 1 d .
H2 H 0.8634 0.2953 0.6498 0.021 Uiso 1 1 calc R
N2 N 0.70229(18) 0.30953(12) 0.61803(10) 0.0175(5) Uani 1 1 d .
C21 C 0.7076(2) 0.39608(15) 0.61587(13) 0.0208(6) Uani 1 1 d .
C22 C 0.6396(2) 0.42369(15) 0.67025(14) 0.0264(7) Uani 1 1 d .
H22A H 0.5623 0.4032 0.6579 0.040 Uiso 1 1 calc R
H22B H 0.6368 0.4799 0.6701 0.040 Uiso 1 1 calc R
H22C H 0.6765 0.4056 0.7173 0.040 Uiso 1 1 calc R
C23 C 0.6515(2) 0.41994(15) 0.54076(13) 0.0275(7) Uani 1 1 d .
H23A H 0.5742 0.3994 0.5289 0.041 Uiso 1 1 calc R
H23B H 0.6955 0.3996 0.5077 0.041 Uiso 1 1 calc R
H23C H 0.6490 0.4761 0.5376 0.041 Uiso 1 1 calc R
C24 C 0.8276(2) 0.42727(15) 0.63436(14) 0.0259(7) Uani 1 1 d .
H24A H 0.8631 0.4120 0.6826 0.039 Uiso 1 1 calc R
H24B H 0.8256 0.4834 0.6310 0.039 Uiso 1 1 calc R
H24C H 0.8715 0.4066 0.6014 0.039 Uiso 1 1 calc R
Sb2 Sb 0.196162(16) 0.244268(10) 0.613595(9) 0.01923(6) Uani 1 1 d .
Cl4 Cl 0.35007(6) 0.24218(4) 0.71505(3) 0.02665(17) Uani 1 1 d .
Cl5 Cl 0.10280(6) 0.33396(4) 0.67724(4) 0.03089(18) Uani 1 1 d .
Cl6 Cl 0.10317(6) 0.13790(4) 0.65378(4) 0.03438(19) 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'
N N 0.0061 0.0033 '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'
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_3
Cl1 Sb1 N2 81.54(5) .
Cl1 Sb1 N1 81.15(5) .
N2 Sb1 N1 70.43(7) .
Cl1 Sb1 Cl2 87.05(2) .
N2 Sb1 Cl2 99.10(6) .
N1 Sb1 Cl2 165.19(5) .
Cl1 Sb1 Cl3 86.08(2) .
N2 Sb1 Cl3 166.07(5) .
N1 Sb1 Cl3 101.44(5) .
Cl2 Sb1 Cl3 86.55(2) .
Cl1 Sb1 Cl4 149.17(2) .
N2 Sb1 Cl4 124.25(5) .
N1 Sb1 Cl4 121.02(4) .
Cl2 Sb1 Cl4 73.372(19) .
Cl3 Sb1 Cl4 69.522(19) .
Sb1 Cl1 Sb2 103.85(2) 7_556
Sb1 Cl2 Sb2 89.654(19) .
Sb1 Cl3 Sb2 92.23(2) .
C1 N1 C11 121.6(2) .
C1 N1 Sb1 112.00(17) .
C11 N1 Sb1 125.28(16) .
N1 C11 C12 113.0(2) .
N1 C11 C14 107.9(2) .
C12 C11 C14 110.0(2) .
N1 C11 C13 104.93(19) .
C12 C11 C13 110.6(2) .
C14 C11 C13 110.3(2) .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C11 C13 H13A 109.5 .
C11 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C11 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
C11 C14 H14A 109.5 .
C11 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C11 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
N1 C1 C2 121.6(3) .
N1 C1 H1 119.2 .
C2 C1 H1 119.2 .
N2 C2 C1 121.7(2) .
N2 C2 H2 119.1 .
C1 C2 H2 119.1 .
C2 N2 C21 120.8(2) .
C2 N2 Sb1 113.39(17) .
C21 N2 Sb1 125.13(16) .
N2 C21 C24 113.3(2) .
N2 C21 C23 106.6(2) .
C24 C21 C23 109.7(2) .
N2 C21 C22 105.13(19) .
C24 C21 C22 110.1(2) .
C23 C21 C22 112.0(2) .
C21 C22 H22A 109.5 .
C21 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C21 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C21 C23 H23A 109.5 .
C21 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C21 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C21 C24 H24A 109.5 .
C21 C24 H24B 109.5 .
H24A C24 H24B 109.5 .
C21 C24 H24C 109.5 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
Cl6 Sb2 Cl4 93.23(3) .
Cl6 Sb2 Cl5 91.98(3) .
Cl4 Sb2 Cl5 87.38(2) .
Cl6 Sb2 Cl3 91.01(2) .
Cl4 Sb2 Cl3 77.80(2) .
Cl5 Sb2 Cl3 165.02(2) .
Cl6 Sb2 Cl2 159.25(2) .
Cl4 Sb2 Cl2 78.33(2) .
Cl5 Sb2 Cl2 106.36(2) .
Cl3 Sb2 Cl2 68.787(18) .
Cl6 Sb2 Cl1 83.07(2) 7_556
Cl4 Sb2 Cl1 160.34(2) 7_556
Cl5 Sb2 Cl1 73.51(2) 7_556
Cl3 Sb2 Cl1 121.435(18) 7_556
Cl2 Sb2 Cl1 111.029(17) 7_556
Sb2 Cl4 Sb1 88.232(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sb1 Cl1 2.3841(6) .
Sb1 N2 2.418(2) .
Sb1 N1 2.460(2) .
Sb1 Cl2 2.5464(7) .
Sb1 Cl3 2.5962(7) .
Sb1 Cl4 3.3633(6) .
Cl1 Sb2 3.3336(7) 7_556
Cl2 Sb2 3.1963(7) .
Cl3 Sb2 3.0408(7) .
N1 C1 1.278(3) .
N1 C11 1.508(3) .
C11 C12 1.524(4) .
C11 C14 1.526(3) .
C11 C13 1.541(3) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C1 C2 1.472(3) .
C1 H1 0.9500 .
C2 N2 1.277(3) .
C2 H2 0.9500 .
N2 C21 1.510(3) .
C21 C24 1.517(4) .
C21 C23 1.529(3) .
C21 C22 1.542(3) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
Sb2 Cl6 2.3804(7) .
Sb2 Cl4 2.4061(7) .
Sb2 Cl5 2.4116(7) .
Sb2 Cl1 3.3336(7) 7_556
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
C1 H1 Cl6 0.95 3.00 3.844(3) 148.8 1_655
C2 H2 Cl5 0.95 2.90 3.829(3) 164.9 1_655
C22 H22B Cl6 0.98 2.79 3.764(3) 172.0 3
C13 H13B Cl5 0.98 2.88 3.820(3) 160.0 3_545
C24 H24A Cl5 0.98 2.99 3.926(3) 160.1 2_656
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_4
N2 Sb1 Cl1 Sb2 -134.92(6) . 7_556
N1 Sb1 Cl1 Sb2 153.72(5) . 7_556
Cl2 Sb1 Cl1 Sb2 -35.26(2) . 7_556
Cl3 Sb1 Cl1 Sb2 51.48(2) . 7_556
Cl4 Sb1 Cl1 Sb2 14.53(5) . 7_556
Cl1 Sb1 Cl2 Sb2 122.81(2) . .
N2 Sb1 Cl2 Sb2 -156.25(4) . .
N1 Sb1 Cl2 Sb2 159.9(2) . .
Cl3 Sb1 Cl2 Sb2 36.561(19) . .
Cl4 Sb1 Cl2 Sb2 -33.087(16) . .
Cl1 Sb1 Cl3 Sb2 -126.07(2) . .
N2 Sb1 Cl3 Sb2 -153.3(2) . .
N1 Sb1 Cl3 Sb2 153.79(4) . .
Cl2 Sb1 Cl3 Sb2 -38.80(2) . .
Cl4 Sb1 Cl3 Sb2 34.731(16) . .
Cl1 Sb1 N1 C1 91.47(15) . .
N2 Sb1 N1 C1 7.36(15) . .
Cl2 Sb1 N1 C1 53.9(3) . .
Cl3 Sb1 N1 C1 175.61(15) . .
Cl4 Sb1 N1 C1 -111.54(15) . .
Cl1 Sb1 N1 C11 -100.53(17) . .
N2 Sb1 N1 C11 175.36(18) . .
Cl2 Sb1 N1 C11 -138.09(18) . .
Cl3 Sb1 N1 C11 -16.39(17) . .
Cl4 Sb1 N1 C11 56.47(18) . .
C1 N1 C11 C12 -8.4(3) . .
Sb1 N1 C11 C12 -175.32(15) . .
C1 N1 C11 C14 -130.3(2) . .
Sb1 N1 C11 C14 62.8(2) . .
C1 N1 C11 C13 112.1(2) . .
Sb1 N1 C11 C13 -54.8(3) . .
C11 N1 C1 C2 -175.57(19) . .
Sb1 N1 C1 C2 -7.1(3) . .
N1 C1 C2 N2 0.1(3) . .
C1 C2 N2 C21 177.88(19) . .
C1 C2 N2 Sb1 7.1(3) . .
Cl1 Sb1 N2 C2 -90.92(16) . .
N1 Sb1 N2 C2 -7.37(15) . .
Cl2 Sb1 N2 C2 -176.53(15) . .
Cl3 Sb1 N2 C2 -63.4(3) . .
Cl4 Sb1 N2 C2 107.45(15) . .
Cl1 Sb1 N2 C21 98.73(17) . .
N1 Sb1 N2 C21 -177.71(18) . .
Cl2 Sb1 N2 C21 13.12(17) . .
Cl3 Sb1 N2 C21 126.3(2) . .
Cl4 Sb1 N2 C21 -62.90(18) . .
C2 N2 C21 C24 3.8(3) . .
Sb1 N2 C21 C24 173.45(15) . .
C2 N2 C21 C23 124.5(2) . .
Sb1 N2 C21 C23 -65.8(2) . .
C2 N2 C21 C22 -116.5(2) . .
Sb1 N2 C21 C22 53.2(3) . .
Sb1 Cl3 Sb2 Cl6 -142.84(3) . .
Sb1 Cl3 Sb2 Cl4 -49.76(2) . .
Sb1 Cl3 Sb2 Cl5 -41.31(9) . .
Sb1 Cl3 Sb2 Cl2 32.310(19) . .
Sb1 Cl3 Sb2 Cl1 134.660(19) . 7_556
Sb1 Cl2 Sb2 Cl6 -19.19(7) . .
Sb1 Cl2 Sb2 Cl4 48.30(2) . .
Sb1 Cl2 Sb2 Cl5 132.03(2) . .
Sb1 Cl2 Sb2 Cl3 -32.994(19) . .
Sb1 Cl2 Sb2 Cl1 -149.747(18) . 7_556
Cl6 Sb2 Cl4 Sb1 126.43(2) . .
Cl5 Sb2 Cl4 Sb1 -141.73(2) . .
Cl3 Sb2 Cl4 Sb1 36.089(16) . .
Cl2 Sb2 Cl4 Sb1 -34.438(15) . .
Cl1 Sb2 Cl4 Sb1 -155.17(5) 7_556 .
Cl1 Sb1 Cl4 Sb2 -6.23(5) . .
N2 Sb1 Cl4 Sb2 136.30(6) . .
N1 Sb1 Cl4 Sb2 -137.33(6) . .
Cl2 Sb1 Cl4 Sb2 46.51(2) . .
Cl3 Sb1 Cl4 Sb2 -46.04(2) . .
