# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1020707'
_audit_update_record             
;
2015-04-04 deposited with the CCDC.
2015-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H44 N2 Sb, F6 P, 2(C H2 Cl2)'
_chemical_formula_sum            'C40 H48 Cl4 F6 N2 P Sb'
_chemical_formula_weight         965.32

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'
N N 0.0061 0.0033 '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'
P P 0.1023 0.0942 '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'
H H 0.0000 0.0000 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   10.3364(4)
_cell_length_b                   24.8372(7)
_cell_length_c                   16.7958(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.284(3)
_cell_angle_gamma                90
_cell_volume                     4266.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    6764
_cell_measurement_theta_min      2.9211
_cell_measurement_theta_max      25.9992

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             1960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.992
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.75110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 5
_diffrn_standards_interval_time  50
_diffrn_reflns_number            19369
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.927
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7483
_reflns_number_gt                4640
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7483
_refine_ls_number_parameters     516
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_restrained_S_all      0.844
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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
C8 C -0.1635(4) 0.18497(14) 0.2092(2) 0.0259(9) Uani 1 1 d . . . . .
C9 C -0.1666(4) 0.18132(15) 0.1253(2) 0.0332(11) Uani 1 1 d . . . . .
C10 C -0.2705(5) 0.15326(18) 0.0825(3) 0.0502(14) Uani 1 1 d . . . . .
H10 H -0.2776 0.1511 0.0267 0.060 Uiso 1 1 calc R U . . .
C11 C -0.3625(5) 0.12876(18) 0.1214(3) 0.0540(14) Uani 1 1 d . . . . .
H11 H -0.4305 0.1097 0.0917 0.065 Uiso 1 1 calc R U . . .
C12 C -0.3558(5) 0.13184(16) 0.2028(3) 0.0436(12) Uani 1 1 d . . . . .
H12 H -0.4199 0.1150 0.2275 0.052 Uiso 1 1 calc R U . . .
C13 C -0.2552(4) 0.15972(14) 0.2503(2) 0.0306(10) Uani 1 1 d . . . . .
C14 C -0.0604(5) 0.20409(15) 0.0821(2) 0.0365(11) Uani 1 1 d . . . . .
H14 H 0.0048 0.2210 0.1226 0.044 Uiso 1 1 calc R U . . .
C15 C 0.0085(5) 0.15910(17) 0.0415(3) 0.0499(14) Uani 1 1 d . . . . .
H15A H 0.0755 0.1745 0.0144 0.075 Uiso 1 1 calc R U . . .
H15B H -0.0540 0.1407 0.0032 0.075 Uiso 1 1 calc R U . . .
H15C H 0.0472 0.1341 0.0816 0.075 Uiso 1 1 calc R U . . .
C16 C -0.1112(5) 0.24740(17) 0.0208(3) 0.0545(15) Uani 1 1 d . . . . .
H16A H -0.0404 0.2606 -0.0050 0.082 Uiso 1 1 calc R U . . .
H16B H -0.1478 0.2766 0.0478 0.082 Uiso 1 1 calc R U . . .
H16C H -0.1774 0.2323 -0.0189 0.082 Uiso 1 1 calc R U . . .
C17 C -0.2497(4) 0.15986(14) 0.3412(2) 0.0283(10) Uani 1 1 d . . . . .
H17 H -0.1878 0.1877 0.3635 0.034 Uiso 1 1 calc R U . . .
C19 C -0.1999(5) 0.10548(15) 0.3761(3) 0.0382(11) Uani 1 1 d . . . . .
H19A H -0.1967 0.1060 0.4335 0.057 Uiso 1 1 calc R U . . .
H19B H -0.1139 0.0989 0.3630 0.057 Uiso 1 1 calc R U . . .
H19C H -0.2578 0.0774 0.3537 0.057 Uiso 1 1 calc R U . . .
C18 C -0.3819(4) 0.17196(16) 0.3679(3) 0.0357(11) Uani 1 1 d . . . . .
H18A H -0.3729 0.1716 0.4256 0.054 Uiso 1 1 calc R U . . .
H18B H -0.4441 0.1451 0.3465 0.054 Uiso 1 1 calc R U . . .
H18C H -0.4116 0.2068 0.3483 0.054 Uiso 1 1 calc R U . . .
C7 C 0.0314(4) 0.19128(16) 0.3006(2) 0.0249(9) Uani 1 1 d . . . . .
H7 H 0.0311 0.1539 0.3032 0.030 Uiso 1 1 calc R U . . .
C2 C 0.1363(4) 0.22166(14) 0.3481(2) 0.0226(9) Uani 1 1 d . . . . .
C1 C 0.1374(4) 0.27702(14) 0.3400(2) 0.0200(9) Uani 1 1 d . . . . .
C6 C 0.2382(4) 0.30580(16) 0.3825(2) 0.0271(9) Uani 1 1 d . . . . .
H6 H 0.2422 0.3429 0.3761 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3353(4) 0.27944(15) 0.4356(2) 0.0289(10) Uani 1 1 d . . . . .
H5 H 0.4014 0.2993 0.4656 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3328(4) 0.22397(16) 0.4435(2) 0.0315(10) Uani 1 1 d . . . . .
H4 H 0.3972 0.2065 0.4785 0.038 Uiso 1 1 calc R U . . .
C3 C 0.2340(4) 0.19493(16) 0.3992(2) 0.0278(9) Uani 1 1 d . . . . .
H3 H 0.2325 0.1576 0.4033 0.033 Uiso 1 1 calc R U . . .
C27 C 0.1554(4) 0.42893(13) 0.2714(2) 0.0215(9) Uani 1 1 d . . . . .
C32 C 0.2381(4) 0.45105(14) 0.3367(2) 0.0242(9) Uani 1 1 d . . . . .
C31 C 0.3487(4) 0.47794(14) 0.3203(3) 0.0289(10) Uani 1 1 d . . . . .
H31 H 0.4050 0.4932 0.3624 0.035 Uiso 1 1 calc R U . . .
C30 C 0.3774(4) 0.48250(15) 0.2426(3) 0.0315(10) Uani 1 1 d . . . . .
H30 H 0.4539 0.4994 0.2329 0.038 Uiso 1 1 calc R U . . .
C29 C 0.2916(4) 0.46182(15) 0.1797(2) 0.0296(10) Uani 1 1 d . . . . .
H29 H 0.3106 0.4659 0.1276 0.035 Uiso 1 1 calc R U . . .
C28 C 0.1787(4) 0.43525(14) 0.1911(2) 0.0251(9) Uani 1 1 d . . . . .
C36 C 0.2086(4) 0.44981(15) 0.4239(2) 0.0282(9) Uani 1 1 d . . . . .
H36 H 0.1400 0.4230 0.4270 0.034 Uiso 1 1 calc R U . . .
C38 C 0.3270(4) 0.43422(17) 0.4843(2) 0.0390(11) Uani 1 1 d . . . . .
H38A H 0.3595 0.3999 0.4698 0.059 Uiso 1 1 calc R U . . .
H38B H 0.3020 0.4320 0.5371 0.059 Uiso 1 1 calc R U . . .
H38C H 0.3940 0.4610 0.4842 0.059 Uiso 1 1 calc R U . . .
C37 C 0.1569(5) 0.50466(16) 0.4472(3) 0.0412(12) Uani 1 1 d . . . . .
H37A H 0.0824 0.5146 0.4091 0.062 Uiso 1 1 calc R U . . .
H37B H 0.2241 0.5313 0.4472 0.062 Uiso 1 1 calc R U . . .
H37C H 0.1318 0.5024 0.4999 0.062 Uiso 1 1 calc R U . . .
C33 C 0.0760(4) 0.42000(16) 0.1203(2) 0.0307(10) Uani 1 1 d . . . . .
H33 H 0.0235 0.3905 0.1377 0.037 Uiso 1 1 calc R U . . .
C35 C 0.1338(5) 0.4010(2) 0.0467(3) 0.0594(15) Uani 1 1 d . . . . .
H35A H 0.0644 0.3920 0.0045 0.089 Uiso 1 1 calc R U . . .
H35B H 0.1871 0.3697 0.0605 0.089 Uiso 1 1 calc R U . . .
H35C H 0.1864 0.4291 0.0288 0.089 Uiso 1 1 calc R U . . .
C34 C -0.0150(5) 0.46836(16) 0.0985(3) 0.0430(12) Uani 1 1 d . . . . .
H34A H -0.0801 0.4590 0.0539 0.065 Uiso 1 1 calc R U . . .
H34B H 0.0352 0.4984 0.0840 0.065 Uiso 1 1 calc R U . . .
H34C H -0.0570 0.4779 0.1439 0.065 Uiso 1 1 calc R U . . .
C26 C -0.0550(4) 0.41920(15) 0.3118(2) 0.0220(9) Uani 1 1 d . . . . .
H26 H -0.0540 0.4559 0.3232 0.026 Uiso 1 1 calc R U . . .
C21 C -0.1671(4) 0.38678(14) 0.3246(2) 0.0224(9) Uani 1 1 d . . . . .
C20 C -0.1659(4) 0.33207(14) 0.3044(2) 0.0225(9) Uani 1 1 d . . . . .
C25 C -0.2771(4) 0.30190(15) 0.3110(2) 0.0281(9) Uani 1 1 d . . . . .
H25 H -0.2796 0.2656 0.2971 0.034 Uiso 1 1 calc R U . . .
C24 C -0.3836(4) 0.32529(17) 0.3381(3) 0.0362(11) Uani 1 1 d . . . . .
H24 H -0.4576 0.3047 0.3419 0.043 Uiso 1 1 calc R U . . .
C23 C -0.3817(4) 0.37909(16) 0.3595(3) 0.0359(11) Uani 1 1 d . . . . .
H23 H -0.4532 0.3943 0.3789 0.043 Uiso 1 1 calc R U . . .
C22 C -0.2745(4) 0.40991(16) 0.3520(2) 0.0288(10) Uani 1 1 d . . . . .
H22 H -0.2736 0.4463 0.3652 0.035 Uiso 1 1 calc R U . . .
N1 N -0.0599(3) 0.21583(11) 0.25564(18) 0.0210(7) Uani 1 1 d . . . . .
N2 N 0.0429(3) 0.39749(11) 0.28490(18) 0.0217(7) Uani 1 1 d . . . . .
F1 F 0.3599(3) 0.44505(10) 0.68910(16) 0.0618(8) Uani 1 1 d . . . . .
F2 F 0.2391(3) 0.37494(9) 0.72131(18) 0.0600(8) Uani 1 1 d . . . . .
F3 F 0.3652(3) 0.42179(12) 0.81733(17) 0.0720(9) Uani 1 1 d . . . . .
F4 F 0.2646(3) 0.49857(8) 0.77339(14) 0.0428(7) Uani 1 1 d . . . . .
F5 F 0.1449(3) 0.45198(10) 0.6736(2) 0.0793(11) Uani 1 1 d . . . . .
F6 F 0.1494(3) 0.42822(10) 0.8062(2) 0.0846(12) Uani 1 1 d . . . . .
P1 P 0.25222(12) 0.43658(4) 0.74743(7) 0.0373(3) Uani 1 1 d . . . . .
Sb1 Sb -0.00620(3) 0.30740(2) 0.24574(2) 0.02091(8) Uani 1 1 d . . . . .
C39 C -0.4112(6) 0.4157(3) 0.1040(3) 0.091(2) Uani 1 1 d . . . . .
H39A H -0.3779 0.4509 0.1219 0.109 Uiso 1 1 calc R U . . .
H39B H -0.4654 0.4028 0.1426 0.109 Uiso 1 1 calc R U . . .
Cl1 Cl -0.28442(15) 0.37340(6) 0.10351(8) 0.0638(4) Uani 1 1 d . . . . .
Cl2 Cl -0.51010(13) 0.42282(6) 0.00858(8) 0.0622(4) Uani 1 1 d . . . . .
C40 C 0.4085(8) 0.2713(4) 0.6596(6) 0.092(4) Uani 0.75 1 d D U P A 1
H40A H 0.3925 0.3035 0.6269 0.110 Uiso 0.75 1 calc R U P A 1
H40B H 0.4327 0.2829 0.7149 0.110 Uiso 0.75 1 calc R U P A 1
Cl3 Cl 0.2620(3) 0.23550(11) 0.65341(17) 0.1083(9) Uani 0.75 1 d D U P A 1
Cl4 Cl 0.53289(17) 0.23977(7) 0.63178(11) 0.0613(5) Uani 0.75 1 d D U P A 1
Cl4' Cl 0.3604(7) 0.1731(2) 0.6864(4) 0.0766(19) Uani 0.25 1 d D U P B 2
Cl3' Cl 0.3160(13) 0.2824(3) 0.6538(7) 0.147(5) Uani 0.25 1 d D U P B 2
C40' C 0.335(3) 0.2381(6) 0.7210(10) 0.075(7) Uani 0.25 1 d D U P B 2
H40C H 0.2575 0.2376 0.7478 0.090 Uiso 0.25 1 calc R U P B 2
H40D H 0.4084 0.2479 0.7606 0.090 Uiso 0.25 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C8 C13 1.398(5) . ?
C8 C9 1.409(5) . ?
C8 N1 1.450(5) . ?
C9 C10 1.390(6) . ?
C9 C14 1.510(6) . ?
C10 C11 1.372(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.361(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.400(6) . ?
C12 H12 0.9300 . ?
C13 C17 1.521(5) . ?
C14 C16 1.529(5) . ?
C14 C15 1.536(5) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.527(6) . ?
C17 C19 1.531(5) . ?
C17 H17 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C7 N1 1.275(5) . ?
C7 C2 1.460(5) . ?
C7 H7 0.9300 . ?
C2 C1 1.382(5) . ?
C2 C3 1.396(5) . ?
C1 C6 1.376(5) . ?
C1 Sb1 2.145(4) . ?
C6 C5 1.405(5) . ?
C6 H6 0.9300 . ?
C5 C4 1.385(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.377(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C27 C32 1.401(5) . ?
C27 C28 1.412(5) . ?
C27 N2 1.445(5) . ?
C32 C31 1.386(5) . ?
C32 C36 1.539(5) . ?
C31 C30 1.384(5) . ?
C31 H31 0.9300 . ?
C30 C29 1.376(6) . ?
C30 H30 0.9300 . ?
C29 C28 1.378(5) . ?
C29 H29 0.9300 . ?
C28 C33 1.523(5) . ?
C36 C38 1.523(5) . ?
C36 C37 1.535(5) . ?
C36 H36 0.9800 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C33 C35 1.524(6) . ?
C33 C34 1.538(6) . ?
C33 H33 0.9800 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C26 N2 1.285(5) . ?
C26 C21 1.452(5) . ?
C26 H26 0.9300 . ?
C21 C22 1.386(5) . ?
C21 C20 1.401(5) . ?
C20 C25 1.390(5) . ?
C20 Sb1 2.131(4) . ?
C25 C24 1.379(5) . ?
C25 H25 0.9300 . ?
C24 C23 1.383(5) . ?
C24 H24 0.9300 . ?
C23 C22 1.368(6) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
N1 Sb1 2.353(3) . ?
N2 Sb1 2.367(3) . ?
F1 P1 1.599(3) . ?
F2 P1 1.593(3) . ?
F3 P1 1.575(3) . ?
F4 P1 1.600(2) . ?
F5 P1 1.586(3) . ?
F6 P1 1.566(3) . ?
C39 Cl1 1.682(6) . ?
C39 Cl2 1.781(6) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 Cl4 1.631(8) . ?
C40 Cl3 1.746(10) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
Cl4' C40' 1.748(15) . ?
Cl3' C40' 1.568(16) . ?
C40' H40C 0.9700 . ?
C40' H40D 0.9700 . ?

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
C13 C8 C9 123.0(4) . . ?
C13 C8 N1 118.2(3) . . ?
C9 C8 N1 118.7(3) . . ?
C10 C9 C8 117.0(4) . . ?
C10 C9 C14 120.0(4) . . ?
C8 C9 C14 122.9(4) . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 121.7(4) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C8 C13 C12 116.2(4) . . ?
C8 C13 C17 124.4(4) . . ?
C12 C13 C17 119.3(4) . . ?
C9 C14 C16 112.6(4) . . ?
C9 C14 C15 110.9(3) . . ?
C16 C14 C15 110.5(3) . . ?
C9 C14 H14 107.6 . . ?
C16 C14 H14 107.6 . . ?
C15 C14 H14 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 C18 112.9(3) . . ?
C13 C17 C19 110.1(3) . . ?
C18 C17 C19 109.1(3) . . ?
C13 C17 H17 108.2 . . ?
C18 C17 H17 108.2 . . ?
C19 C17 H17 108.2 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C7 C2 120.3(4) . . ?
N1 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C1 C2 C3 121.2(4) . . ?
C1 C2 C7 118.5(4) . . ?
C3 C2 C7 120.3(3) . . ?
C6 C1 C2 118.8(4) . . ?
C6 C1 Sb1 126.3(3) . . ?
C2 C1 Sb1 114.1(3) . . ?
C1 C6 C5 120.4(4) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C32 C27 C28 122.3(4) . . ?
C32 C27 N2 120.2(3) . . ?
C28 C27 N2 117.5(3) . . ?
C31 C32 C27 117.4(3) . . ?
C31 C32 C36 118.8(3) . . ?
C27 C32 C36 123.7(3) . . ?
C30 C31 C32 121.5(4) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 H31 119.3 . . ?
C29 C30 C31 119.4(4) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C30 C29 C28 122.5(4) . . ?
C30 C29 H29 118.7 . . ?
C28 C29 H29 118.7 . . ?
C29 C28 C27 116.8(4) . . ?
C29 C28 C33 121.3(3) . . ?
C27 C28 C33 121.5(4) . . ?
C38 C36 C37 109.3(3) . . ?
C38 C36 C32 112.9(3) . . ?
C37 C36 C32 110.4(3) . . ?
C38 C36 H36 108.0 . . ?
C37 C36 H36 108.0 . . ?
C32 C36 H36 108.0 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C28 C33 C35 113.6(4) . . ?
C28 C33 C34 109.0(3) . . ?
C35 C33 C34 110.3(4) . . ?
C28 C33 H33 107.9 . . ?
C35 C33 H33 107.9 . . ?
C34 C33 H33 107.9 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N2 C26 C21 120.3(3) . . ?
N2 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C22 C21 C20 121.2(4) . . ?
C22 C21 C26 120.9(3) . . ?
C20 C21 C26 117.9(3) . . ?
C25 C20 C21 117.9(4) . . ?
C25 C20 Sb1 125.9(3) . . ?
C21 C20 Sb1 115.2(3) . . ?
C24 C25 C20 120.5(4) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
C25 C24 C23 120.7(4) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C22 C23 C24 119.9(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C22 C21 119.8(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C7 N1 C8 119.5(3) . . ?
C7 N1 Sb1 110.0(3) . . ?
C8 N1 Sb1 129.5(2) . . ?
C26 N2 C27 121.4(3) . . ?
C26 N2 Sb1 110.3(2) . . ?
C27 N2 Sb1 127.8(2) . . ?
F6 P1 F3 89.8(2) . . ?
F6 P1 F5 93.6(2) . . ?
F3 P1 F5 176.6(2) . . ?
F6 P1 F2 90.45(15) . . ?
F3 P1 F2 90.32(16) . . ?
F5 P1 F2 89.68(15) . . ?
F6 P1 F1 178.7(2) . . ?
F3 P1 F1 88.89(17) . . ?
F5 P1 F1 87.68(18) . . ?
F2 P1 F1 89.81(15) . . ?
F6 P1 F4 89.46(14) . . ?
F3 P1 F4 89.99(15) . . ?
F5 P1 F4 90.02(14) . . ?
F2 P1 F4 179.68(19) . . ?
F1 P1 F4 90.28(14) . . ?
C20 Sb1 C1 105.03(13) . . ?
C20 Sb1 N1 92.24(12) . . ?
C1 Sb1 N1 75.69(12) . . ?
C20 Sb1 N2 75.46(13) . . ?
C1 Sb1 N2 91.69(12) . . ?
N1 Sb1 N2 159.67(10) . . ?
Cl1 C39 Cl2 113.8(3) . . ?
Cl1 C39 H39A 108.8 . . ?
Cl2 C39 H39A 108.8 . . ?
Cl1 C39 H39B 108.8 . . ?
Cl2 C39 H39B 108.8 . . ?
H39A C39 H39B 107.7 . . ?
Cl4 C40 Cl3 116.8(6) . . ?
Cl4 C40 H40A 108.1 . . ?
Cl3 C40 H40A 108.1 . . ?
Cl4 C40 H40B 108.1 . . ?
Cl3 C40 H40B 108.1 . . ?
H40A C40 H40B 107.3 . . ?
Cl3' C40' Cl4' 114.7(11) . . ?
Cl3' C40' H40C 108.6 . . ?
Cl4' C40' H40C 108.6 . . ?
Cl3' C40' H40D 108.6 . . ?
Cl4' C40' H40D 108.6 . . ?
H40C C40' H40D 107.6 . . ?

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
C13 C8 C9 C10 3.3(6) . . . . ?
N1 C8 C9 C10 -177.4(4) . . . . ?
C13 C8 C9 C14 -173.9(4) . . . . ?
N1 C8 C9 C14 5.4(6) . . . . ?
C8 C9 C10 C11 -2.3(7) . . . . ?
C14 C9 C10 C11 175.0(4) . . . . ?
C9 C10 C11 C12 0.9(8) . . . . ?
C10 C11 C12 C13 -0.3(8) . . . . ?
C9 C8 C13 C12 -2.7(6) . . . . ?
N1 C8 C13 C12 178.0(4) . . . . ?
C9 C8 C13 C17 175.9(4) . . . . ?
N1 C8 C13 C17 -3.4(6) . . . . ?
C11 C12 C13 C8 1.1(7) . . . . ?
C11 C12 C13 C17 -177.5(4) . . . . ?
C10 C9 C14 C16 63.9(5) . . . . ?
C8 C9 C14 C16 -119.0(4) . . . . ?
C10 C9 C14 C15 -60.4(5) . . . . ?
C8 C9 C14 C15 116.7(4) . . . . ?
C8 C13 C17 C18 134.7(4) . . . . ?
C12 C13 C17 C18 -46.8(5) . . . . ?
C8 C13 C17 C19 -103.1(4) . . . . ?
C12 C13 C17 C19 75.5(5) . . . . ?
N1 C7 C2 C1 -3.1(5) . . . . ?
N1 C7 C2 C3 178.0(3) . . . . ?
C3 C2 C1 C6 1.0(5) . . . . ?
C7 C2 C1 C6 -177.9(3) . . . . ?
C3 C2 C1 Sb1 171.5(3) . . . . ?
C7 C2 C1 Sb1 -7.4(4) . . . . ?
C2 C1 C6 C5 -2.6(5) . . . . ?
Sb1 C1 C6 C5 -171.8(3) . . . . ?
C1 C6 C5 C4 2.3(6) . . . . ?
C6 C5 C4 C3 -0.3(6) . . . . ?
C5 C4 C3 C2 -1.2(6) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C7 C2 C3 C4 179.8(3) . . . . ?
C28 C27 C32 C31 -2.7(5) . . . . ?
N2 C27 C32 C31 176.1(3) . . . . ?
C28 C27 C32 C36 173.7(3) . . . . ?
N2 C27 C32 C36 -7.5(5) . . . . ?
C27 C32 C31 C30 -0.5(5) . . . . ?
C36 C32 C31 C30 -177.1(3) . . . . ?
C32 C31 C30 C29 2.7(6) . . . . ?
C31 C30 C29 C28 -1.7(6) . . . . ?
C30 C29 C28 C27 -1.3(6) . . . . ?
C30 C29 C28 C33 171.0(4) . . . . ?
C32 C27 C28 C29 3.6(5) . . . . ?
N2 C27 C28 C29 -175.2(3) . . . . ?
C32 C27 C28 C33 -168.7(3) . . . . ?
N2 C27 C28 C33 12.5(5) . . . . ?
C31 C32 C36 C38 -48.1(5) . . . . ?
C27 C32 C36 C38 135.5(4) . . . . ?
C31 C32 C36 C37 74.7(4) . . . . ?
C27 C32 C36 C37 -101.7(4) . . . . ?
C29 C28 C33 C35 38.8(5) . . . . ?
C27 C28 C33 C35 -149.3(4) . . . . ?
C29 C28 C33 C34 -84.6(4) . . . . ?
C27 C28 C33 C34 87.3(4) . . . . ?
N2 C26 C21 C22 -178.6(3) . . . . ?
N2 C26 C21 C20 -1.8(5) . . . . ?
C22 C21 C20 C25 1.5(5) . . . . ?
C26 C21 C20 C25 -175.4(3) . . . . ?
C22 C21 C20 Sb1 170.4(3) . . . . ?
C26 C21 C20 Sb1 -6.5(4) . . . . ?
C21 C20 C25 C24 -1.2(5) . . . . ?
Sb1 C20 C25 C24 -168.8(3) . . . . ?
C20 C25 C24 C23 -0.3(6) . . . . ?
C25 C24 C23 C22 1.6(6) . . . . ?
C24 C23 C22 C21 -1.4(6) . . . . ?
C20 C21 C22 C23 -0.2(6) . . . . ?
C26 C21 C22 C23 176.6(4) . . . . ?
C2 C7 N1 C8 -179.7(3) . . . . ?
C2 C7 N1 Sb1 10.6(4) . . . . ?
C13 C8 N1 C7 71.5(5) . . . . ?
C9 C8 N1 C7 -107.8(4) . . . . ?
C13 C8 N1 Sb1 -121.1(3) . . . . ?
C9 C8 N1 Sb1 59.5(5) . . . . ?
C21 C26 N2 C27 179.7(3) . . . . ?
C21 C26 N2 Sb1 8.0(4) . . . . ?
C32 C27 N2 C26 67.8(5) . . . . ?
C28 C27 N2 C26 -113.3(4) . . . . ?
C32 C27 N2 Sb1 -122.0(3) . . . . ?
C28 C27 N2 Sb1 56.8(4) . . . . ?

_refine_diff_density_max         0.817
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1020708'
_audit_update_record             
;
2015-04-04 deposited with the CCDC.
2015-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H32 N2 Sb, F6 P, 2(C H Cl3)'
_chemical_formula_sum            'C34 H34 Cl6 F6 N2 P Sb'
_chemical_formula_weight         950.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.0562 5.8946 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.2715(12)
_cell_length_b                   12.4401(9)
_cell_length_c                   15.1691(10)
_cell_angle_alpha                80.778(6)
_cell_angle_beta                 71.653(8)
_cell_angle_gamma                70.246(8)
_cell_volume                     2064.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6501
_cell_measurement_theta_min      3.0723
_cell_measurement_theta_max      61.9945

_exptl_crystal_description       block
_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    9.708
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.63723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  20
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11151
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         62.084
_diffrn_reflns_theta_full        62.500
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             6479
_reflns_number_gt                5226
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;

_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1062P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6479
_refine_ls_number_parameters     589
_refine_ls_number_restraints     418
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.970
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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
C1 C 0.2382(5) 0.1340(5) 0.5977(3) 0.0603(13) Uani 1 1 d . . . . .
C6 C 0.1985(6) 0.2127(6) 0.5329(4) 0.0702(15) Uani 1 1 d . . . . .
H6 H 0.2337 0.2706 0.5088 0.084 Uiso 1 1 calc R U . . .
C5 C 0.1053(7) 0.2070(7) 0.5026(5) 0.0842(19) Uani 1 1 d . . . . .
H5 H 0.0778 0.2614 0.4584 0.101 Uiso 1 1 calc R U . . .
C4 C 0.0527(7) 0.1205(7) 0.5378(5) 0.090(2) Uani 1 1 d . . . . .
H4 H -0.0113 0.1180 0.5186 0.108 Uiso 1 1 calc R U . . .
C3 C 0.0962(7) 0.0383(7) 0.6015(5) 0.0842(19) Uani 1 1 d . . . . .
H3 H 0.0627 -0.0208 0.6246 0.101 Uiso 1 1 calc R U . . .
C2 C 0.1910(6) 0.0442(5) 0.6313(4) 0.0698(15) Uani 1 1 d . . . . .
C7 C 0.2406(6) -0.0430(5) 0.6948(4) 0.0711(15) Uani 1 1 d . . . . .
H7 H 0.2104 -0.1045 0.7159 0.085 Uiso 1 1 calc R U . . .
C8 C 0.3700(5) -0.1167(5) 0.7922(4) 0.0624(13) Uani 1 1 d . . . . .
C9 C 0.2918(6) -0.1328(6) 0.8790(4) 0.0733(16) Uani 1 1 d . . . . .
C10 C 0.3412(7) -0.2019(6) 0.9456(5) 0.0836(18) Uani 1 1 d . . . . .
H10 H 0.2901 -0.2112 1.0043 0.100 Uiso 1 1 calc R U . . .
C11 C 0.4628(8) -0.2580(6) 0.9298(5) 0.087(2) Uani 1 1 d . . . . .
C12 C 0.5365(6) -0.2429(6) 0.8424(5) 0.0803(17) Uani 1 1 d . . . . .
H12 H 0.6187 -0.2810 0.8306 0.096 Uiso 1 1 calc R U . . .
C13 C 0.4950(6) -0.1737(5) 0.7707(4) 0.0690(15) Uani 1 1 d . . . . .
C14 C 0.1571(7) -0.0704(7) 0.9064(5) 0.094(2) Uani 1 1 d . . . . .
H14A H 0.1348 -0.0256 0.8535 0.141 Uiso 1 1 calc R U . . .
H14B H 0.1379 -0.0211 0.9554 0.141 Uiso 1 1 calc R U . . .
H14C H 0.1136 -0.1252 0.9278 0.141 Uiso 1 1 calc R U . . .
C15 C 0.5137(10) -0.3331(9) 1.0053(6) 0.123(3) Uani 1 1 d . . . . .
H15A H 0.5996 -0.3647 0.9814 0.185 Uiso 1 1 calc R U . . .
H15B H 0.4784 -0.3941 1.0255 0.185 Uiso 1 1 calc R U . . .
H15C H 0.4955 -0.2883 1.0570 0.185 Uiso 1 1 calc R U . . .
C16 C 0.5795(6) -0.1693(6) 0.6758(5) 0.0817(18) Uani 1 1 d . . . . .
H16A H 0.5365 -0.1179 0.6350 0.123 Uiso 1 1 calc R U . . .
H16B H 0.6133 -0.2444 0.6524 0.123 Uiso 1 1 calc R U . . .
H16C H 0.6431 -0.1428 0.6787 0.123 Uiso 1 1 calc R U . . .
C17 C 0.3033(5) 0.2086(5) 0.7751(3) 0.0592(13) Uani 1 1 d . . . . .
C22 C 0.2819(6) 0.1566(6) 0.8624(4) 0.0727(16) Uani 1 1 d . . . . .
H22 H 0.3016 0.0773 0.8701 0.087 Uiso 1 1 calc R U . . .
C21 C 0.2306(7) 0.2224(7) 0.9399(4) 0.087(2) Uani 1 1 d . . . . .
H21 H 0.2164 0.1861 0.9991 0.104 Uiso 1 1 calc R U . . .
C20 C 0.2007(7) 0.3389(6) 0.9308(4) 0.0831(19) Uani 1 1 d . . . . .
H20 H 0.1654 0.3814 0.9833 0.100 Uiso 1 1 calc R U . . .
C19 C 0.2234(6) 0.3937(6) 0.8425(4) 0.0738(16) Uani 1 1 d . . . . .
H19 H 0.2033 0.4730 0.8352 0.089 Uiso 1 1 calc R U . . .
C18 C 0.2772(5) 0.3270(5) 0.7648(4) 0.0616(13) Uani 1 1 d . . . . .
C23 C 0.3136(5) 0.3796(5) 0.6728(4) 0.0641(13) Uani 1 1 d . . . . .
H23 H 0.3005 0.4582 0.6657 0.077 Uiso 1 1 calc R U . . .
C24 C 0.4002(6) 0.3718(5) 0.5096(4) 0.0652(14) Uani 1 1 d . . . . .
C25 C 0.5242(6) 0.3333(5) 0.4606(4) 0.0702(15) Uani 1 1 d . . . . .
C26 C 0.5588(7) 0.3760(6) 0.3689(5) 0.0843(19) Uani 1 1 d . . . . .
H26 H 0.6397 0.3512 0.3352 0.101 Uiso 1 1 calc R U . . .
C27 C 0.4773(8) 0.4542(7) 0.3262(5) 0.092(2) Uani 1 1 d . . . . .
C28 C 0.3592(8) 0.4920(6) 0.3787(5) 0.0859(19) Uani 1 1 d . . . . .
H28 H 0.3041 0.5467 0.3515 0.103 Uiso 1 1 calc R U . . .
C29 C 0.3180(6) 0.4533(5) 0.4696(4) 0.0737(16) Uani 1 1 d . . . . .
C30 C 0.6179(6) 0.2518(6) 0.5036(5) 0.0880(19) Uani 1 1 d . . . . .
H30A H 0.5799 0.2304 0.5665 0.132 Uiso 1 1 calc R U . . .
H30B H 0.6758 0.2881 0.5033 0.132 Uiso 1 1 calc R U . . .
H30C H 0.6580 0.1847 0.4685 0.132 Uiso 1 1 calc R U . . .
C31 C 0.5177(9) 0.4933(9) 0.2243(5) 0.118(3) Uani 1 1 d . . . . .
H31A H 0.6029 0.4576 0.2000 0.177 Uiso 1 1 calc R U . . .
H31B H 0.5006 0.5749 0.2188 0.177 Uiso 1 1 calc R U . . .
H31C H 0.4753 0.4721 0.1899 0.177 Uiso 1 1 calc R U . . .
C32 C 0.1830(7) 0.5038(7) 0.5198(6) 0.100(2) Uani 1 1 d . . . . .
H32A H 0.1660 0.4700 0.5821 0.150 Uiso 1 1 calc R U . . .
H32B H 0.1356 0.4876 0.4868 0.150 Uiso 1 1 calc R U . . .
H32C H 0.1633 0.5851 0.5216 0.150 Uiso 1 1 calc R U . . .
N1 N 0.3255(4) -0.0363(4) 0.7223(3) 0.0615(11) Uani 1 1 d . . . . .
P1 P 0.0092(6) -0.2791(6) 0.7636(5) 0.084(2) Uani 0.762(19) 1 d D U P A 1
F1 F 0.0518(14) -0.4004(6) 0.7280(7) 0.155(4) Uani 0.762(19) 1 d D U P A 1
F2 F -0.0063(14) -0.3488(13) 0.8578(7) 0.176(5) Uani 0.762(19) 1 d D U P A 1
F3 F -0.1279(9) -0.2469(10) 0.7795(15) 0.198(6) Uani 0.762(19) 1 d D U P A 1
F4 F 0.1456(8) -0.3075(15) 0.7532(13) 0.197(6) Uani 0.762(19) 1 d D U P A 1
F5 F 0.028(2) -0.2176(12) 0.6657(8) 0.208(7) Uani 0.762(19) 1 d D U P A 1
F6 F -0.0157(16) -0.1661(11) 0.8088(12) 0.173(6) Uani 0.762(19) 1 d D U P A 1
P1' P 0.0183(18) -0.2820(18) 0.7582(14) 0.086(7) Uani 0.238(19) 1 d D U P A 2
F1' F -0.019(4) -0.356(4) 0.7058(17) 0.129(9) Uani 0.238(19) 1 d D U P A 2
F2' F -0.069(3) -0.309(3) 0.8481(14) 0.141(12) Uani 0.238(19) 1 d D U P A 2
F3' F -0.085(2) -0.248(3) 0.7179(17) 0.116(8) Uani 0.238(19) 1 d D U P A 2
F4' F 0.116(3) -0.306(3) 0.809(3) 0.174(15) Uani 0.238(19) 1 d D U P A 2
F5' F 0.099(3) -0.246(3) 0.668(2) 0.167(13) Uani 0.238(19) 1 d D U P A 2
F6' F -0.007(3) -0.155(2) 0.771(3) 0.118(8) Uani 0.238(19) 1 d D U P A 2
Sb1 Sb 0.38940(3) 0.12281(3) 0.64725(2) 0.05912(16) Uani 1 1 d . . . . .
C33 C -0.2596(16) 0.0485(18) 0.7715(12) 0.099(5) Uani 0.455(18) 1 d D U P B 1
H33 H -0.2082 -0.0185 0.7987 0.119 Uiso 0.455(18) 1 calc R U P B 1
Cl1 Cl -0.224(2) 0.166(2) 0.7786(15) 0.290(12) Uani 0.455(18) 1 d D U P B 1
Cl2 Cl -0.4080(11) 0.0660(17) 0.8316(10) 0.189(6) Uani 0.455(18) 1 d D U P B 1
Cl3 Cl -0.2333(7) 0.0299(7) 0.6556(5) 0.126(3) Uani 0.455(18) 1 d D U P B 1
C33' C -0.255(2) 0.026(3) 0.7871(14) 0.170(9) Uani 0.545(18) 1 d D U P B 2
H33' H -0.2024 -0.0523 0.7755 0.204 Uiso 0.545(18) 1 calc R U P B 2
Cl1' Cl -0.1834(9) 0.1017(14) 0.8170(10) 0.218(6) Uani 0.545(18) 1 d D U P B 2
Cl2' Cl -0.3798(13) 0.0256(12) 0.8790(15) 0.233(6) Uani 0.545(18) 1 d D U P B 2
Cl3' Cl -0.300(2) 0.0878(19) 0.6924(16) 0.302(9) Uani 0.545(18) 1 d D U P B 2
N2 N 0.3629(4) 0.3213(4) 0.6015(3) 0.0590(10) Uani 1 1 d . . . . .
C34 C -0.0869(19) 0.4066(16) 0.8378(14) 0.123(7) Uani 0.531(19) 1 d D U P C 1
H34 H -0.0337 0.4545 0.8234 0.148 Uiso 0.531(19) 1 calc R U P C 1
Cl4 Cl -0.0070(9) 0.2812(13) 0.7876(13) 0.198(6) Uani 0.531(19) 1 d D U P C 1
Cl5 Cl -0.2089(15) 0.4795(17) 0.7988(17) 0.273(9) Uani 0.531(19) 1 d D U P C 1
Cl6 Cl -0.1293(13) 0.3795(10) 0.9565(8) 0.201(5) Uani 0.531(19) 1 d D U P C 1
C34' C -0.081(2) 0.403(2) 0.8313(12) 0.116(10) Uani 0.469(19) 1 d D U P C 2
H34' H -0.0416 0.4614 0.8267 0.139 Uiso 0.469(19) 1 calc R U P C 2
Cl4' Cl -0.0133(15) 0.3287(16) 0.7342(13) 0.219(8) Uani 0.469(19) 1 d D U P C 2
Cl5' Cl -0.2283(12) 0.4711(16) 0.8373(11) 0.192(6) Uani 0.469(19) 1 d D U P C 2
Cl6' Cl -0.0802(17) 0.326(2) 0.9347(14) 0.255(9) Uani 0.469(19) 1 d D U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C6 1.353(8) . ?
C1 C2 1.383(8) . ?
C1 Sb1 2.167(5) . ?
C6 C5 1.386(9) . ?
C6 H6 0.9300 . ?
C5 C4 1.388(11) . ?
C5 H5 0.9300 . ?
C4 C3 1.380(10) . ?
C4 H4 0.9300 . ?
C3 C2 1.400(9) . ?
C3 H3 0.9300 . ?
C2 C7 1.437(9) . ?
C7 N1 1.268(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(8) . ?
C8 C13 1.410(9) . ?
C8 N1 1.442(7) . ?
C9 C10 1.373(10) . ?
C9 C14 1.520(10) . ?
C10 C11 1.376(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(10) . ?
C11 C15 1.513(10) . ?
C12 C13 1.390(9) . ?
C12 H12 0.9300 . ?
C13 C16 1.492(9) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.364(8) . ?
C17 C18 1.391(8) . ?
C17 Sb1 2.151(5) . ?
C22 C21 1.394(9) . ?
C22 H22 0.9300 . ?
C21 C20 1.364(10) . ?
C21 H21 0.9300 . ?
C20 C19 1.391(9) . ?
C20 H20 0.9300 . ?
C19 C18 1.402(8) . ?
C19 H19 0.9300 . ?
C18 C23 1.446(8) . ?
C23 N2 1.266(7) . ?
C23 H23 0.9300 . ?
C24 C29 1.382(9) . ?
C24 C25 1.417(9) . ?
C24 N2 1.435(7) . ?
C25 C26 1.393(9) . ?
C25 C30 1.500(10) . ?
C26 C27 1.384(11) . ?
C26 H26 0.9300 . ?
C27 C28 1.374(12) . ?
C27 C31 1.520(9) . ?
C28 C29 1.380(9) . ?
C28 H28 0.9300 . ?
C29 C32 1.541(10) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
N1 Sb1 2.365(4) . ?
P1 F3 1.540(9) . ?
P1 F2 1.540(9) . ?
P1 F5 1.544(9) . ?
P1 F1 1.547(9) . ?
P1 F4 1.551(9) . ?
P1 F6 1.557(9) . ?
P1' F3' 1.487(17) . ?
P1' F2' 1.512(17) . ?
P1' F5' 1.518(17) . ?
P1' F4' 1.540(18) . ?
P1' F6' 1.542(18) . ?
P1' F1' 1.561(17) . ?
F1' F3' 1.32(6) . ?
Sb1 N2 2.395(4) . ?
C33 Cl1 1.693(16) . ?
C33 Cl2 1.717(16) . ?
C33 Cl3 1.722(16) . ?
C33 H33 0.9800 . ?
C33' Cl3' 1.676(18) . ?
C33' Cl1' 1.678(17) . ?
C33' Cl2' 1.716(18) . ?
C33' H33' 0.9800 . ?
C34 Cl4 1.688(16) . ?
C34 Cl5 1.698(16) . ?
C34 Cl6 1.720(17) . ?
C34 H34 0.9800 . ?
C34' Cl4' 1.693(17) . ?
C34' Cl5' 1.697(18) . ?
C34' Cl6' 1.703(17) . ?
C34' H34' 0.9800 . ?

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
C6 C1 C2 121.0(5) . . ?
C6 C1 Sb1 125.2(4) . . ?
C2 C1 Sb1 113.5(4) . . ?
C1 C6 C5 119.9(6) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C5 C4 120.5(7) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C3 C4 C5 119.3(7) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C3 C2 119.9(7) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 C7 120.0(6) . . ?
C3 C2 C7 120.7(6) . . ?
N1 C7 C2 120.3(5) . . ?
N1 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C9 C8 C13 121.9(6) . . ?
C9 C8 N1 120.5(5) . . ?
C13 C8 N1 117.6(5) . . ?
C10 C9 C8 117.7(6) . . ?
C10 C9 C14 118.3(6) . . ?
C8 C9 C14 123.8(6) . . ?
C9 C10 C11 123.3(7) . . ?
C9 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C12 C11 C10 117.2(6) . . ?
C12 C11 C15 121.2(8) . . ?
C10 C11 C15 121.6(8) . . ?
C11 C12 C13 123.7(7) . . ?
C11 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C12 C13 C8 116.1(6) . . ?
C12 C13 C16 120.3(6) . . ?
C8 C13 C16 123.4(6) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 119.3(5) . . ?
C22 C17 Sb1 125.8(4) . . ?
C18 C17 Sb1 114.8(4) . . ?
C17 C22 C21 120.0(6) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C20 C21 C22 121.4(6) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C20 C19 119.7(6) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C19 C18 118.7(6) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C17 C18 C19 120.9(5) . . ?
C17 C18 C23 118.6(5) . . ?
C19 C18 C23 120.4(5) . . ?
N2 C23 C18 121.6(5) . . ?
N2 C23 H23 119.2 . . ?
C18 C23 H23 119.2 . . ?
C29 C24 C25 121.1(6) . . ?
C29 C24 N2 121.3(5) . . ?
C25 C24 N2 117.5(5) . . ?
C26 C25 C24 117.5(6) . . ?
C26 C25 C30 119.6(6) . . ?
C24 C25 C30 123.0(5) . . ?
C27 C26 C25 122.4(7) . . ?
C27 C26 H26 118.8 . . ?
C25 C26 H26 118.8 . . ?
C28 C27 C26 117.4(6) . . ?
C28 C27 C31 122.0(8) . . ?
C26 C27 C31 120.6(8) . . ?
C27 C28 C29 123.5(7) . . ?
C27 C28 H28 118.3 . . ?
C29 C28 H28 118.3 . . ?
C28 C29 C24 118.0(7) . . ?
C28 C29 C32 117.6(6) . . ?
C24 C29 C32 124.4(6) . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C31 H31A 109.5 . . ?
C27 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C27 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C7 N1 C8 121.6(5) . . ?
C7 N1 Sb1 110.9(4) . . ?
C8 N1 Sb1 127.4(4) . . ?
F3 P1 F2 88.3(7) . . ?
F3 P1 F5 92.7(8) . . ?
F2 P1 F5 175.8(9) . . ?
F3 P1 F1 101.0(10) . . ?
F2 P1 F1 80.9(7) . . ?
F5 P1 F1 94.9(8) . . ?
F3 P1 F4 176.3(10) . . ?
F2 P1 F4 90.0(7) . . ?
F5 P1 F4 89.2(8) . . ?
F1 P1 F4 82.0(11) . . ?
F3 P1 F6 87.3(8) . . ?
F2 P1 F6 93.2(9) . . ?
F5 P1 F6 90.9(8) . . ?
F1 P1 F6 169.6(10) . . ?
F4 P1 F6 89.6(9) . . ?
F3' P1' F2' 86.1(15) . . ?
F3' P1' F5' 91.5(15) . . ?
F2' P1' F5' 176(2) . . ?
F3' P1' F4' 173(2) . . ?
F2' P1' F4' 90.2(17) . . ?
F5' P1' F4' 91.8(17) . . ?
F3' P1' F6' 88.5(17) . . ?
F2' P1' F6' 98(2) . . ?
F5' P1' F6' 78(2) . . ?
F4' P1' F6' 86.1(16) . . ?
F3' P1' F1' 51(2) . . ?
F2' P1' F1' 89.9(14) . . ?
F5' P1' F1' 91.4(17) . . ?
F4' P1' F1' 135(3) . . ?
F6' P1' F1' 139(3) . . ?
F3' F1' P1' 61.4(13) . . ?
F1' F3' P1' 67.2(16) . . ?
C17 Sb1 C1 102.9(2) . . ?
C17 Sb1 N1 89.23(19) . . ?
C1 Sb1 N1 75.16(19) . . ?
C17 Sb1 N2 75.21(19) . . ?
C1 Sb1 N2 89.18(19) . . ?
N1 Sb1 N2 155.02(16) . . ?
Cl1 C33 Cl2 109.5(14) . . ?
Cl1 C33 Cl3 108.2(13) . . ?
Cl2 C33 Cl3 111.2(11) . . ?
Cl1 C33 H33 109.3 . . ?
Cl2 C33 H33 109.3 . . ?
Cl3 C33 H33 109.3 . . ?
Cl3' C33' Cl1' 110.8(15) . . ?
Cl3' C33' Cl2' 109.1(15) . . ?
Cl1' C33' Cl2' 106.8(14) . . ?
Cl3' C33' H33' 110.0 . . ?
Cl1' C33' H33' 110.0 . . ?
Cl2' C33' H33' 110.0 . . ?
C23 N2 C24 122.5(5) . . ?
C23 N2 Sb1 109.7(4) . . ?
C24 N2 Sb1 127.7(3) . . ?
Cl4 C34 Cl5 113.2(13) . . ?
Cl4 C34 Cl6 108.6(12) . . ?
Cl5 C34 Cl6 110.8(14) . . ?
Cl4 C34 H34 108.0 . . ?
Cl5 C34 H34 108.0 . . ?
Cl6 C34 H34 108.0 . . ?
Cl4' C34' Cl5' 109.6(14) . . ?
Cl4' C34' Cl6' 116.5(17) . . ?
Cl5' C34' Cl6' 105.8(13) . . ?
Cl4' C34' H34' 108.2 . . ?
Cl5' C34' H34' 108.2 . . ?
Cl6' C34' H34' 108.2 . . ?

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
C2 C1 C6 C5 3.0(9) . . . . ?
Sb1 C1 C6 C5 176.1(5) . . . . ?
C1 C6 C5 C4 -0.4(11) . . . . ?
C6 C5 C4 C3 -1.7(12) . . . . ?
C5 C4 C3 C2 1.2(12) . . . . ?
C6 C1 C2 C3 -3.5(9) . . . . ?
Sb1 C1 C2 C3 -177.3(5) . . . . ?
C6 C1 C2 C7 175.4(6) . . . . ?
Sb1 C1 C2 C7 1.6(7) . . . . ?
C4 C3 C2 C1 1.3(10) . . . . ?
C4 C3 C2 C7 -177.6(7) . . . . ?
C1 C2 C7 N1 1.9(9) . . . . ?
C3 C2 C7 N1 -179.2(6) . . . . ?
C13 C8 C9 C10 3.5(9) . . . . ?
N1 C8 C9 C10 -173.7(6) . . . . ?
C13 C8 C9 C14 178.0(6) . . . . ?
N1 C8 C9 C14 0.8(9) . . . . ?
C8 C9 C10 C11 -2.0(11) . . . . ?
C14 C9 C10 C11 -176.8(7) . . . . ?
C9 C10 C11 C12 -0.1(11) . . . . ?
C9 C10 C11 C15 179.8(8) . . . . ?
C10 C11 C12 C13 0.8(11) . . . . ?
C15 C11 C12 C13 -179.1(8) . . . . ?
C11 C12 C13 C8 0.6(10) . . . . ?
C11 C12 C13 C16 -175.1(7) . . . . ?
C9 C8 C13 C12 -2.8(9) . . . . ?
N1 C8 C13 C12 174.5(5) . . . . ?
C9 C8 C13 C16 172.8(6) . . . . ?
N1 C8 C13 C16 -10.0(9) . . . . ?
C18 C17 C22 C21 2.2(10) . . . . ?
Sb1 C17 C22 C21 176.8(5) . . . . ?
C17 C22 C21 C20 0.0(11) . . . . ?
C22 C21 C20 C19 -1.0(12) . . . . ?
C21 C20 C19 C18 -0.2(11) . . . . ?
C22 C17 C18 C19 -3.5(9) . . . . ?
Sb1 C17 C18 C19 -178.7(5) . . . . ?
C22 C17 C18 C23 172.7(6) . . . . ?
Sb1 C17 C18 C23 -2.5(7) . . . . ?
C20 C19 C18 C17 2.5(9) . . . . ?
C20 C19 C18 C23 -173.6(6) . . . . ?
C17 C18 C23 N2 3.5(9) . . . . ?
C19 C18 C23 N2 179.7(6) . . . . ?
C29 C24 C25 C26 -3.4(9) . . . . ?
N2 C24 C25 C26 175.3(5) . . . . ?
C29 C24 C25 C30 175.2(6) . . . . ?
N2 C24 C25 C30 -6.0(9) . . . . ?
C24 C25 C26 C27 0.8(10) . . . . ?
C30 C25 C26 C27 -178.0(6) . . . . ?
C25 C26 C27 C28 2.0(10) . . . . ?
C25 C26 C27 C31 -176.4(7) . . . . ?
C26 C27 C28 C29 -2.4(11) . . . . ?
C31 C27 C28 C29 176.1(7) . . . . ?
C27 C28 C29 C24 -0.2(11) . . . . ?
C27 C28 C29 C32 180.0(7) . . . . ?
C25 C24 C29 C28 3.2(9) . . . . ?
N2 C24 C29 C28 -175.5(6) . . . . ?
C25 C24 C29 C32 -177.0(7) . . . . ?
N2 C24 C29 C32 4.3(10) . . . . ?
C2 C7 N1 C8 174.4(5) . . . . ?
C2 C7 N1 Sb1 -4.0(7) . . . . ?
C9 C8 N1 C7 -56.0(8) . . . . ?
C13 C8 N1 C7 126.7(6) . . . . ?
C9 C8 N1 Sb1 122.2(5) . . . . ?
C13 C8 N1 Sb1 -55.1(7) . . . . ?
F2' P1' F1' F3' 85.1(19) . . . . ?
F5' P1' F1' F3' -90.7(18) . . . . ?
F4' P1' F1' F3' 175(3) . . . . ?
F6' P1' F1' F3' -17(3) . . . . ?
F2' P1' F3' F1' -93.0(18) . . . . ?
F5' P1' F3' F1' 91(2) . . . . ?
F6' P1' F3' F1' 169(2) . . . . ?
C18 C23 N2 C24 -179.7(5) . . . . ?
C18 C23 N2 Sb1 -2.4(7) . . . . ?
C29 C24 N2 C23 -61.5(8) . . . . ?
C25 C24 N2 C23 119.7(6) . . . . ?
C29 C24 N2 Sb1 121.7(5) . . . . ?
C25 C24 N2 Sb1 -57.0(7) . . . . ?

_refine_diff_density_max         0.880
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.118

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_577r
_database_code_depnum_ccdc_archive 'CCDC 1020709'
_audit_update_record             
;
2015-04-04 deposited with the CCDC.
2015-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H44 F N2 Sb'
_chemical_formula_sum            'C38 H44 F N2 Sb'
_chemical_formula_weight         669.50

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

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'

_cell_length_a                   14.847(11)
_cell_length_b                   21.755(16)
_cell_length_c                   10.693(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3454(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5582
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      21.98

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.831
_shelx_estimated_absorpt_T_min   0.777
_shelx_estimated_absorpt_T_max   0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7769
_exptl_absorpt_correction_T_max  0.8129
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21151
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.661
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             6049
_reflns_number_gt                5253
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.962

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+0.1810P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2071 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6049
_refine_ls_number_parameters     387
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.4457(4) 0.1075(3) 0.9111(10) 0.0391(17) Uani 1 1 d . . . . .
C2 C 0.4547(5) 0.0649(3) 0.8092(7) 0.0392(17) Uani 1 1 d . . . . .
C3 C 0.4055(5) 0.0106(4) 0.8105(9) 0.057(2) Uani 1 1 d . . . . .
H3 H 0.4127 -0.0177 0.7461 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3458(5) -0.0017(4) 0.9073(14) 0.069(3) Uani 1 1 d . . . . .
H4 H 0.3127 -0.0379 0.9079 0.083 Uiso 1 1 calc R U . . .
C5 C 0.3364(6) 0.0395(5) 1.0004(10) 0.067(3) Uani 1 1 d . . . . .
H5 H 0.2954 0.0317 1.0642 0.080 Uiso 1 1 calc R U . . .
C6 C 0.3862(6) 0.0934(4) 1.0035(9) 0.058(2) Uani 1 1 d . . . . .
H6 H 0.3789 0.1205 1.0701 0.070 Uiso 1 1 calc R U . . .
C7 C 0.5122(5) 0.0795(4) 0.7027(8) 0.0461(19) Uani 1 1 d . . . . .
H7 H 0.5158 0.0514 0.6374 0.055 Uiso 1 1 calc R U . . .
C8 C 0.5981(5) 0.1444(3) 0.5765(8) 0.0424(18) Uani 1 1 d . . . . .
C9 C 0.5443(6) 0.1535(4) 0.4718(9) 0.050(2) Uani 1 1 d . . . . .
C10 C 0.5875(7) 0.1677(4) 0.3587(8) 0.059(3) Uani 1 1 d . . . . .
H10 H 0.5533 0.1731 0.2867 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6796(8) 0.1736(5) 0.3525(9) 0.069(3) Uani 1 1 d . . . . .
H11 H 0.7072 0.1824 0.2765 0.083 Uiso 1 1 calc R U . . .
C12 C 0.7312(7) 0.1665(5) 0.4591(10) 0.062(3) Uani 1 1 d . . . . .
H12 H 0.7934 0.1709 0.4543 0.074 Uiso 1 1 calc R U . . .
C13 C 0.6918(5) 0.1530(4) 0.5724(8) 0.052(2) Uani 1 1 d . . . . .
C14 C 0.4415(6) 0.1487(4) 0.4707(9) 0.063(2) Uani 1 1 d . . . . .
H14 H 0.4216 0.1465 0.5580 0.075 Uiso 1 1 calc R U . . .
C15 C 0.3994(7) 0.2055(4) 0.4141(15) 0.083(3) Uani 1 1 d . . . . .
H15A H 0.4164 0.2086 0.3277 0.124 Uiso 1 1 calc R U . . .
H15B H 0.4201 0.2413 0.4583 0.124 Uiso 1 1 calc R U . . .
H15C H 0.3350 0.2028 0.4204 0.124 Uiso 1 1 calc R U . . .
C16 C 0.4084(6) 0.0907(4) 0.4056(16) 0.085(3) Uani 1 1 d . . . . .
H16A H 0.4258 0.0918 0.3191 0.127 Uiso 1 1 calc R U . . .
H16B H 0.3439 0.0885 0.4115 0.127 Uiso 1 1 calc R U . . .
H16C H 0.4345 0.0553 0.4450 0.127 Uiso 1 1 calc R U . . .
C17 C 0.7510(6) 0.1454(5) 0.6866(9) 0.060(2) Uani 1 1 d . . . . .
H17 H 0.7116 0.1487 0.7599 0.072 Uiso 1 1 calc R U . . .
C18 C 0.8211(9) 0.1959(6) 0.6985(15) 0.107(5) Uani 1 1 d . . . . .
H18A H 0.8550 0.1901 0.7740 0.161 Uiso 1 1 calc R U . . .
H18B H 0.7915 0.2352 0.7011 0.161 Uiso 1 1 calc R U . . .
H18C H 0.8609 0.1945 0.6279 0.161 Uiso 1 1 calc R U . . .
C19 C 0.7937(12) 0.0828(7) 0.6914(15) 0.130(6) Uani 1 1 d . . . . .
H19A H 0.8273 0.0759 0.6160 0.195 Uiso 1 1 calc R U . . .
H19B H 0.7477 0.0521 0.6992 0.195 Uiso 1 1 calc R U . . .
H19C H 0.8335 0.0805 0.7621 0.195 Uiso 1 1 calc R U . . .
C20 C 0.6385(5) 0.1594(3) 0.9782(7) 0.0388(17) Uani 1 1 d . . . . .
C21 C 0.7114(5) 0.1992(3) 1.0042(8) 0.0447(19) Uani 1 1 d . . . . .
C22 C 0.7947(6) 0.1753(5) 1.0413(8) 0.050(2) Uani 1 1 d . . . . .
H22 H 0.8426 0.2016 1.0585 0.060 Uiso 1 1 calc R U . . .
C23 C 0.8058(7) 0.1120(5) 1.0525(9) 0.065(3) Uani 1 1 d . . . . .
H23 H 0.8619 0.0959 1.0729 0.078 Uiso 1 1 calc R U . . .
C24 C 0.7348(7) 0.0737(4) 1.0335(10) 0.069(3) Uani 1 1 d . . . . .
H24 H 0.7411 0.0317 1.0462 0.083 Uiso 1 1 calc R U . . .
C25 C 0.6529(6) 0.0977(4) 0.9953(8) 0.054(2) Uani 1 1 d . . . . .
H25 H 0.6055 0.0707 0.9805 0.065 Uiso 1 1 calc R U . . .
C26 C 0.7016(5) 0.2663(4) 0.9966(7) 0.0423(18) Uani 1 1 d . . . . .
H26 H 0.7522 0.2912 1.0040 0.051 Uiso 1 1 calc R U . . .
C27 C 0.6131(5) 0.3560(4) 0.9748(8) 0.0400(19) Uani 1 1 d . . . . .
C28 C 0.6165(6) 0.3873(5) 0.8616(7) 0.058(3) Uani 1 1 d . . . . .
C29 C 0.5956(8) 0.4487(5) 0.8576(10) 0.077(3) Uani 1 1 d . . . . .
H29 H 0.5978 0.4703 0.7826 0.093 Uiso 1 1 calc R U . . .
C30 C 0.5709(9) 0.4786(5) 0.9695(15) 0.087(4) Uani 1 1 d . . . . .
H30 H 0.5579 0.5204 0.9684 0.104 Uiso 1 1 calc R U . . .
C31 C 0.5657(7) 0.4472(4) 1.0785(11) 0.071(3) Uani 1 1 d . . . . .
H31 H 0.5475 0.4677 1.1504 0.085 Uiso 1 1 calc R U . . .
C32 C 0.5868(6) 0.3852(4) 1.0857(9) 0.052(2) Uani 1 1 d . . . . .
C33 C 0.6426(7) 0.3528(5) 0.7408(9) 0.072(3) Uani 1 1 d . . . . .
H33 H 0.6518 0.3097 0.7643 0.087 Uiso 1 1 calc R U . . .
C34 C 0.7296(8) 0.3752(7) 0.6900(13) 0.122(5) Uani 1 1 d . . . . .
H34A H 0.7450 0.3520 0.6167 0.183 Uiso 1 1 calc R U . . .
H34B H 0.7758 0.3703 0.7520 0.183 Uiso 1 1 calc R U . . .
H34C H 0.7242 0.4179 0.6686 0.183 Uiso 1 1 calc R U . . .
C35 C 0.5717(10) 0.3535(11) 0.6476(14) 0.173(9) Uani 1 1 d . . . . .
H35A H 0.5747 0.3911 0.6007 0.260 Uiso 1 1 calc R U . . .
H35B H 0.5142 0.3505 0.6882 0.260 Uiso 1 1 calc R U . . .
H35C H 0.5793 0.3192 0.5920 0.260 Uiso 1 1 calc R U . . .
C36 C 0.5830(7) 0.3501(5) 1.2102(8) 0.064(3) Uani 1 1 d . . . . .
H36 H 0.5787 0.3064 1.1885 0.077 Uiso 1 1 calc R U . . .
C37 C 0.6675(9) 0.3573(8) 1.2782(11) 0.127(6) Uani 1 1 d . . . . .
H37A H 0.7170 0.3475 1.2240 0.190 Uiso 1 1 calc R U . . .
H37B H 0.6680 0.3301 1.3490 0.190 Uiso 1 1 calc R U . . .
H37C H 0.6731 0.3990 1.3065 0.190 Uiso 1 1 calc R U . . .
C38 C 0.5026(7) 0.3640(8) 1.2907(11) 0.102(5) Uani 1 1 d . . . . .
H38A H 0.4486 0.3596 1.2421 0.154 Uiso 1 1 calc R U . . .
H38B H 0.5068 0.4054 1.3215 0.154 Uiso 1 1 calc R U . . .
H38C H 0.5010 0.3359 1.3599 0.154 Uiso 1 1 calc R U . . .
N1 N 0.5576(4) 0.1287(3) 0.6951(5) 0.0375(14) Uani 1 1 d . . . . .
N2 N 0.6251(5) 0.2904(3) 0.9798(6) 0.0436(16) Uani 1 1 d . . . . .
F1 F 0.4620(3) 0.2149(2) 1.0660(5) 0.0617(13) Uani 1 1 d . . . . .
Sb1 Sb 0.51462(3) 0.19534(2) 0.89876(10) 0.04108(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C6 1.360(12) . ?
C1 C2 1.436(12) . ?
C1 Sb1 2.172(7) . ?
C2 C3 1.388(10) . ?
C2 C7 1.459(12) . ?
C3 C4 1.389(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.347(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(13) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.268(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(12) . ?
C8 C13 1.403(10) . ?
C8 N1 1.444(9) . ?
C9 C10 1.404(11) . ?
C9 C14 1.530(13) . ?
C10 C11 1.375(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(12) . ?
C12 H12 0.9300 . ?
C13 C17 1.515(13) . ?
C14 C15 1.512(13) . ?
C14 C16 1.523(12) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C19 1.503(16) . ?
C17 C18 1.518(13) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C25 1.372(11) . ?
C20 C21 1.415(11) . ?
C20 Sb1 2.172(7) . ?
C21 C22 1.399(12) . ?
C21 C26 1.468(11) . ?
C22 C23 1.392(13) . ?
C22 H22 0.9300 . ?
C23 C24 1.358(13) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(12) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 N2 1.264(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.390(11) . ?
C27 C32 1.400(12) . ?
C27 N2 1.440(10) . ?
C28 C29 1.372(15) . ?
C28 C33 1.543(13) . ?
C29 C30 1.410(16) . ?
C29 H29 0.9300 . ?
C30 C31 1.353(16) . ?
C30 H30 0.9300 . ?
C31 C32 1.386(12) . ?
C31 H31 0.9300 . ?
C32 C36 1.536(12) . ?
C33 C35 1.450(16) . ?
C33 C34 1.483(15) . ?
C33 H33 0.9800 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.459(15) . ?
C36 C38 1.502(14) . ?
C36 H36 0.9800 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
F1 Sb1 1.998(5) . ?

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
C6 C1 C2 117.8(7) . . ?
C6 C1 Sb1 123.2(7) . . ?
C2 C1 Sb1 118.6(6) . . ?
C3 C2 C1 119.5(7) . . ?
C3 C2 C7 120.0(8) . . ?
C1 C2 C7 120.4(6) . . ?
C2 C3 C4 120.4(9) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.3(8) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.7(9) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 121.3(9) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
N1 C7 C2 123.0(7) . . ?
N1 C7 H7 118.5 . . ?
C2 C7 H7 118.5 . . ?
C9 C8 C13 121.7(8) . . ?
C9 C8 N1 120.1(7) . . ?
C13 C8 N1 118.2(7) . . ?
C8 C9 C10 117.6(7) . . ?
C8 C9 C14 124.8(8) . . ?
C10 C9 C14 117.7(8) . . ?
C11 C10 C9 121.1(8) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.0(8) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 121.0(8) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 118.5(9) . . ?
C12 C13 C17 119.1(8) . . ?
C8 C13 C17 122.4(7) . . ?
C15 C14 C16 111.1(9) . . ?
C15 C14 C9 111.1(8) . . ?
C16 C14 C9 112.5(7) . . ?
C15 C14 H14 107.3 . . ?
C16 C14 H14 107.3 . . ?
C9 C14 H14 107.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C17 C13 111.8(8) . . ?
C19 C17 C18 111.3(10) . . ?
C13 C17 C18 112.7(9) . . ?
C19 C17 H17 106.9 . . ?
C13 C17 H17 106.9 . . ?
C18 C17 H17 106.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 117.0(7) . . ?
C25 C20 Sb1 122.5(6) . . ?
C21 C20 Sb1 120.3(5) . . ?
C22 C21 C20 120.3(7) . . ?
C22 C21 C26 118.2(7) . . ?
C20 C21 C26 121.4(7) . . ?
C23 C22 C21 119.7(9) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 120.2(9) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.7(9) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C20 C25 C24 123.0(8) . . ?
C20 C25 H25 118.5 . . ?
C24 C25 H25 118.5 . . ?
N2 C26 C21 120.6(7) . . ?
N2 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C28 C27 C32 121.7(7) . . ?
C28 C27 N2 120.9(8) . . ?
C32 C27 N2 116.9(7) . . ?
C29 C28 C27 119.7(9) . . ?
C29 C28 C33 120.3(9) . . ?
C27 C28 C33 120.0(9) . . ?
C28 C29 C30 118.8(9) . . ?
C28 C29 H29 120.6 . . ?
C30 C29 H29 120.6 . . ?
C31 C30 C29 120.8(9) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C32 121.8(10) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C31 C32 C27 117.2(9) . . ?
C31 C32 C36 121.6(9) . . ?
C27 C32 C36 121.2(8) . . ?
C35 C33 C34 112.1(11) . . ?
C35 C33 C28 112.9(11) . . ?
C34 C33 C28 111.4(9) . . ?
C35 C33 H33 106.6 . . ?
C34 C33 H33 106.6 . . ?
C28 C33 H33 106.6 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 C38 112.1(9) . . ?
C37 C36 C32 110.3(9) . . ?
C38 C36 C32 115.2(9) . . ?
C37 C36 H36 106.2 . . ?
C38 C36 H36 106.2 . . ?
C32 C36 H36 106.2 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C7 N1 C8 118.5(6) . . ?
C26 N2 C27 121.8(7) . . ?
F1 Sb1 C20 93.4(3) . . ?
F1 Sb1 C1 87.1(3) . . ?
C20 Sb1 C1 93.3(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
C6 C1 C2 C3 -2.3(11) . . . . ?
Sb1 C1 C2 C3 -174.9(6) . . . . ?
C6 C1 C2 C7 175.4(7) . . . . ?
Sb1 C1 C2 C7 2.8(10) . . . . ?
C1 C2 C3 C4 2.2(12) . . . . ?
C7 C2 C3 C4 -175.5(8) . . . . ?
C2 C3 C4 C5 -0.4(14) . . . . ?
C3 C4 C5 C6 -1.4(15) . . . . ?
C2 C1 C6 C5 0.6(13) . . . . ?
Sb1 C1 C6 C5 172.8(7) . . . . ?
C4 C5 C6 C1 1.3(15) . . . . ?
C3 C2 C7 N1 178.9(7) . . . . ?
C1 C2 C7 N1 1.2(12) . . . . ?
C13 C8 C9 C10 4.3(13) . . . . ?
N1 C8 C9 C10 -179.0(7) . . . . ?
C13 C8 C9 C14 -176.3(7) . . . . ?
N1 C8 C9 C14 0.5(12) . . . . ?
C8 C9 C10 C11 -1.4(14) . . . . ?
C14 C9 C10 C11 179.1(8) . . . . ?
C9 C10 C11 C12 -1.0(16) . . . . ?
C10 C11 C12 C13 0.5(17) . . . . ?
C11 C12 C13 C8 2.3(15) . . . . ?
C11 C12 C13 C17 179.8(9) . . . . ?
C9 C8 C13 C12 -4.7(12) . . . . ?
N1 C8 C13 C12 178.5(8) . . . . ?
C9 C8 C13 C17 177.8(8) . . . . ?
N1 C8 C13 C17 1.0(11) . . . . ?
C8 C9 C14 C15 128.0(10) . . . . ?
C10 C9 C14 C15 -52.5(12) . . . . ?
C8 C9 C14 C16 -106.7(11) . . . . ?
C10 C9 C14 C16 72.8(12) . . . . ?
C12 C13 C17 C19 -80.3(13) . . . . ?
C8 C13 C17 C19 97.1(12) . . . . ?
C12 C13 C17 C18 46.0(13) . . . . ?
C8 C13 C17 C18 -136.6(9) . . . . ?
C25 C20 C21 C22 2.2(12) . . . . ?
Sb1 C20 C21 C22 -172.4(6) . . . . ?
C25 C20 C21 C26 -176.2(8) . . . . ?
Sb1 C20 C21 C26 9.2(10) . . . . ?
C20 C21 C22 C23 0.0(13) . . . . ?
C26 C21 C22 C23 178.5(8) . . . . ?
C21 C22 C23 C24 -3.3(14) . . . . ?
C22 C23 C24 C25 4.1(16) . . . . ?
C21 C20 C25 C24 -1.4(13) . . . . ?
Sb1 C20 C25 C24 173.1(7) . . . . ?
C23 C24 C25 C20 -1.8(16) . . . . ?
C22 C21 C26 N2 -170.6(7) . . . . ?
C20 C21 C26 N2 7.9(12) . . . . ?
C32 C27 C28 C29 1.5(14) . . . . ?
N2 C27 C28 C29 173.2(8) . . . . ?
C32 C27 C28 C33 -177.8(8) . . . . ?
N2 C27 C28 C33 -6.1(13) . . . . ?
C27 C28 C29 C30 -0.2(16) . . . . ?
C33 C28 C29 C30 179.1(11) . . . . ?
C28 C29 C30 C31 -1.5(19) . . . . ?
C29 C30 C31 C32 1.9(18) . . . . ?
C30 C31 C32 C27 -0.6(15) . . . . ?
C30 C31 C32 C36 178.6(10) . . . . ?
C28 C27 C32 C31 -1.1(13) . . . . ?
N2 C27 C32 C31 -173.1(8) . . . . ?
C28 C27 C32 C36 179.7(9) . . . . ?
N2 C27 C32 C36 7.7(12) . . . . ?
C29 C28 C33 C35 -60.6(16) . . . . ?
C27 C28 C33 C35 118.7(14) . . . . ?
C29 C28 C33 C34 66.6(14) . . . . ?
C27 C28 C33 C34 -114.1(12) . . . . ?
C31 C32 C36 C37 -85.5(13) . . . . ?
C27 C32 C36 C37 93.7(12) . . . . ?
C31 C32 C36 C38 42.6(14) . . . . ?
C27 C32 C36 C38 -138.2(10) . . . . ?
C2 C7 N1 C8 -168.0(7) . . . . ?
C9 C8 N1 C7 60.7(10) . . . . ?
C13 C8 N1 C7 -122.5(8) . . . . ?
C21 C26 N2 C27 178.5(7) . . . . ?
C28 C27 N2 C26 91.8(10) . . . . ?
C32 C27 N2 C26 -96.1(10) . . . . ?

_refine_diff_density_max         1.086
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.073

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_632r
_database_code_depnum_ccdc_archive 'CCDC 1020710'
_audit_update_record             
;
2015-04-04 deposited with the CCDC.
2015-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H27 F N Sb'
_chemical_formula_sum            'C25 H27 F N Sb'
_chemical_formula_weight         482.23

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'Cc   '
_symmetry_space_group_name_Hall  'C -2yc '


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'

_cell_length_a                   15.136(2)
_cell_length_b                   10.038(2)
_cell_length_c                   15.178(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.706(4)
_cell_angle_gamma                90.00
_cell_volume                     2266.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6921
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.20
_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6934
_exptl_absorpt_correction_T_max  0.7477
_exptl_absorpt_process_details   'Bruker, 2001.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10576
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3944
_reflns_number_gt                3879
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0226P)²+0.2070P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(18)
_refine_ls_number_reflns         3944
_refine_ls_number_parameters     257
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0501
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.03578(19) 0.4588(3) 0.80061(19) 0.0421(6) Uani 1 1 d . . .
C2 C 0.0405(2) 0.4326(3) 0.89181(19) 0.0431(7) Uani 1 1 d . . .
C3 C 0.0482(3) 0.3048(3) 0.9243(3) 0.0602(9) Uani 1 1 d . . .
H3 H 0.0515 0.2893 0.9852 0.072 Uiso 1 1 calc R . .
C4 C 0.0512(3) 0.1994(4) 0.8667(3) 0.0692(10) Uani 1 1 d . . .
H4 H 0.0562 0.1126 0.8886 0.083 Uiso 1 1 calc R . .
C5 C 0.0469(3) 0.2229(4) 0.7779(3) 0.0682(10) Uani 1 1 d . . .
H5 H 0.0497 0.1516 0.7394 0.082 Uiso 1 1 calc R . .
C6 C 0.0383(3) 0.3504(3) 0.7438(2) 0.0556(9) Uani 1 1 d . . .
H6 H 0.0341 0.3642 0.6826 0.067 Uiso 1 1 calc R . .
C7 C 0.0386(2) 0.5453(3) 0.95109(19) 0.0467(7) Uani 1 1 d . . .
H7 H 0.0394 0.5312 1.0118 0.056 Uiso 1 1 calc R . .
C8 C 0.0370(2) 0.7774(3) 0.97683(18) 0.0433(6) Uani 1 1 d . . .
C9 C -0.0438(3) 0.8412(3) 0.9791(2) 0.0565(9) Uani 1 1 d . . .
C10 C -0.0396(3) 0.9594(4) 1.0284(3) 0.0727(11) Uani 1 1 d . . .
H10 H -0.0924 1.0047 1.0320 0.087 Uiso 1 1 calc R . .
C11 C 0.0406(4) 1.0089(3) 1.0714(3) 0.0816(13) Uani 1 1 d . . .
H11 H 0.0420 1.0888 1.1027 0.098 Uiso 1 1 calc R . .
C12 C 0.1181(3) 0.9436(4) 1.0691(2) 0.0756(11) Uani 1 1 d . . .
H12 H 0.1719 0.9788 1.1000 0.091 Uiso 1 1 calc R . .
C13 C 0.1198(3) 0.8247(3) 1.0219(2) 0.0558(9) Uani 1 1 d . . .
C14 C -0.1331(3) 0.7853(5) 0.9351(3) 0.0717(10) Uani 1 1 d . . .
H14 H -0.1213 0.7113 0.8968 0.086 Uiso 1 1 calc R . .
C15 C -0.1924(4) 0.8836(7) 0.8765(5) 0.124(2) Uani 1 1 d . . .
H15A H -0.2088 0.9543 0.9129 0.186 Uiso 1 1 calc R . .
H15B H -0.2456 0.8393 0.8463 0.186 Uiso 1 1 calc R . .
H15C H -0.1604 0.9200 0.8330 0.186 Uiso 1 1 calc R . .
C16 C -0.1836(4) 0.7290(7) 1.0050(4) 0.1199(19) Uani 1 1 d . . .
H16A H -0.1472 0.6626 1.0401 0.180 Uiso 1 1 calc R . .
H16B H -0.2389 0.6894 0.9753 0.180 Uiso 1 1 calc R . .
H16C H -0.1964 0.7994 1.0435 0.180 Uiso 1 1 calc R . .
C17 C 0.2067(2) 0.7500(4) 1.0231(3) 0.0650(10) Uani 1 1 d . . .
H17 H 0.1994 0.6958 0.9685 0.078 Uiso 1 1 calc R . .
C18 C 0.2254(4) 0.6564(4) 1.1028(4) 0.0878(14) Uani 1 1 d . . .
H18A H 0.2336 0.7072 1.1573 0.132 Uiso 1 1 calc R . .
H18B H 0.2789 0.6061 1.1007 0.132 Uiso 1 1 calc R . .
H18C H 0.1756 0.5966 1.1009 0.132 Uiso 1 1 calc R . .
C19 C 0.2880(4) 0.8406(5) 1.0244(4) 0.110(2) Uani 1 1 d . . .
H19A H 0.2732 0.9087 0.9797 0.164 Uiso 1 1 calc R . .
H19B H 0.3376 0.7889 1.0119 0.164 Uiso 1 1 calc R . .
H19C H 0.3043 0.8811 1.0824 0.164 Uiso 1 1 calc R . .
C20 C 0.1365(2) 0.7418(3) 0.76746(19) 0.0454(7) Uani 1 1 d . . .
C21 C 0.1474(3) 0.8738(4) 0.7897(3) 0.0661(10) Uani 1 1 d . . .
H21 H 0.0994 0.9216 0.8041 0.079 Uiso 1 1 calc R . .
C22 C 0.2278(4) 0.9361(5) 0.7910(3) 0.0912(15) Uani 1 1 d . . .
H22 H 0.2347 1.0260 0.8056 0.109 Uiso 1 1 calc R . .
C23 C 0.2979(4) 0.8644(8) 0.7706(4) 0.116(2) Uani 1 1 d . . .
H23 H 0.3533 0.9054 0.7723 0.139 Uiso 1 1 calc R . .
C24 C 0.2873(3) 0.7329(8) 0.7478(4) 0.1103(18) Uani 1 1 d . . .
H24 H 0.3352 0.6853 0.7329 0.132 Uiso 1 1 calc R . .
C25 C 0.2073(3) 0.6719(4) 0.7467(3) 0.0737(11) Uani 1 1 d . . .
H25 H 0.2005 0.5822 0.7317 0.088 Uiso 1 1 calc R . .
F1 F 0.01430(15) 0.5975(2) 0.63125(12) 0.0666(5) Uani 1 1 d . . .
N1 N 0.03580(18) 0.6632(2) 0.92048(18) 0.0398(6) Uani 1 1 d . . .
Sb1 Sb 0.006283(17) 0.657194(14) 0.755162(17) 0.04287(6) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
C1 C6 1.393(4) . ?
C1 C2 1.398(4) . ?
C1 Sb1 2.127(3) . ?
C2 C3 1.372(5) . ?
C2 C7 1.449(4) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.270(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(5) . ?
C8 C13 1.394(5) . ?
C8 N1 1.428(4) . ?
C9 C10 1.398(5) . ?
C9 C14 1.500(6) . ?
C10 C11 1.361(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.350(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(5) . ?
C12 H12 0.9300 . ?
C13 C17 1.512(5) . ?
C14 C15 1.508(7) . ?
C14 C16 1.526(7) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.517(6) . ?
C17 C19 1.528(6) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C25 1.366(5) . ?
C20 C21 1.370(5) . ?
C20 Sb1 2.122(3) . ?
C21 C22 1.365(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.364(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.367(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.355(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
F1 Sb1 1.9989(18) . ?
N1 Sb1 2.466(3) . ?

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
C6 C1 C2 117.6(3) . . ?
C6 C1 Sb1 123.9(2) . . ?
C2 C1 Sb1 117.8(2) . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 C7 121.2(3) . . ?
C1 C2 C7 117.7(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C7 C2 120.3(3) . . ?
N1 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C9 C8 C13 123.1(3) . . ?
C9 C8 N1 118.2(3) . . ?
C13 C8 N1 118.6(3) . . ?
C8 C9 C10 116.9(4) . . ?
C8 C9 C14 122.8(3) . . ?
C10 C9 C14 120.2(4) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 121.9(4) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C8 C13 C12 116.3(4) . . ?
C8 C13 C17 122.4(3) . . ?
C12 C13 C17 121.2(4) . . ?
C9 C14 C15 113.9(4) . . ?
C9 C14 C16 110.8(4) . . ?
C15 C14 C16 109.4(4) . . ?
C9 C14 H14 107.5 . . ?
C15 C14 H14 107.5 . . ?
C16 C14 H14 107.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 C18 110.5(3) . . ?
C13 C17 C19 113.7(4) . . ?
C18 C17 C19 109.1(4) . . ?
C13 C17 H17 107.8 . . ?
C18 C17 H17 107.8 . . ?
C19 C17 H17 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 119.3(3) . . ?
C25 C20 Sb1 122.0(3) . . ?
C21 C20 Sb1 118.5(3) . . ?
C22 C21 C20 120.9(4) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 118.9(5) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 120.5(5) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 120.1(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C20 120.2(4) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C7 N1 C8 122.2(3) . . ?
C7 N1 Sb1 109.7(2) . . ?
C8 N1 Sb1 127.52(18) . . ?
F1 Sb1 C20 89.14(10) . . ?
F1 Sb1 C1 88.79(10) . . ?
C20 Sb1 C1 102.16(11) . . ?
F1 Sb1 N1 158.98(9) . . ?
C20 Sb1 N1 84.89(10) . . ?
C1 Sb1 N1 72.89(9) . . ?

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
C6 C1 C2 C3 0.7(5) . . . . ?
Sb1 C1 C2 C3 171.9(3) . . . . ?
C6 C1 C2 C7 179.6(3) . . . . ?
Sb1 C1 C2 C7 -9.2(4) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C7 C2 C3 C4 -179.0(4) . . . . ?
C2 C3 C4 C5 0.3(7) . . . . ?
C3 C4 C5 C6 -0.9(7) . . . . ?
C4 C5 C6 C1 1.4(6) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?
Sb1 C1 C6 C5 -171.9(3) . . . . ?
C3 C2 C7 N1 176.6(3) . . . . ?
C1 C2 C7 N1 -2.3(4) . . . . ?
C13 C8 C9 C10 0.9(5) . . . . ?
N1 C8 C9 C10 -174.4(3) . . . . ?
C13 C8 C9 C14 -176.1(3) . . . . ?
N1 C8 C9 C14 8.5(5) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C14 C9 C10 C11 177.6(4) . . . . ?
C9 C10 C11 C12 -1.5(6) . . . . ?
C10 C11 C12 C13 1.1(6) . . . . ?
C9 C8 C13 C12 -1.3(5) . . . . ?
N1 C8 C13 C12 174.0(3) . . . . ?
C9 C8 C13 C17 176.5(3) . . . . ?
N1 C8 C13 C17 -8.2(5) . . . . ?
C11 C12 C13 C8 0.2(5) . . . . ?
C11 C12 C13 C17 -177.6(3) . . . . ?
C8 C9 C14 C15 -130.5(4) . . . . ?
C10 C9 C14 C15 52.5(6) . . . . ?
C8 C9 C14 C16 105.6(5) . . . . ?
C10 C9 C14 C16 -71.4(5) . . . . ?
C8 C13 C17 C18 -90.7(4) . . . . ?
C12 C13 C17 C18 86.9(4) . . . . ?
C8 C13 C17 C19 146.2(4) . . . . ?
C12 C13 C17 C19 -36.1(5) . . . . ?
C25 C20 C21 C22 0.2(6) . . . . ?
Sb1 C20 C21 C22 -174.4(3) . . . . ?
C20 C21 C22 C23 -0.7(7) . . . . ?
C21 C22 C23 C24 1.1(8) . . . . ?
C22 C23 C24 C25 -1.2(10) . . . . ?
C23 C24 C25 C20 0.7(9) . . . . ?
C21 C20 C25 C24 -0.3(7) . . . . ?
Sb1 C20 C25 C24 174.1(4) . . . . ?
C2 C7 N1 C8 -177.7(3) . . . . ?
C2 C7 N1 Sb1 10.4(4) . . . . ?
C9 C8 N1 C7 -100.8(4) . . . . ?
C13 C8 N1 C7 83.6(4) . . . . ?
C9 C8 N1 Sb1 69.5(3) . . . . ?
C13 C8 N1 Sb1 -106.1(3) . . . . ?
C25 C20 Sb1 F1 -49.5(3) . . . . ?
C21 C20 Sb1 F1 124.9(3) . . . . ?
C25 C20 Sb1 C1 39.1(3) . . . . ?
C21 C20 Sb1 C1 -146.5(3) . . . . ?
C25 C20 Sb1 N1 110.3(3) . . . . ?
C21 C20 Sb1 N1 -75.3(3) . . . . ?
C6 C1 Sb1 F1 -9.5(3) . . . . ?
C2 C1 Sb1 F1 179.8(2) . . . . ?
C6 C1 Sb1 C20 -98.4(3) . . . . ?
C2 C1 Sb1 C20 90.9(2) . . . . ?
C6 C1 Sb1 N1 -179.1(3) . . . . ?
C2 C1 Sb1 N1 10.3(2) . . . . ?
C7 N1 Sb1 F1 -41.5(4) . . . . ?
C8 N1 Sb1 F1 147.2(3) . . . . ?
C7 N1 Sb1 C20 -115.5(2) . . . . ?
C8 N1 Sb1 C20 73.2(3) . . . . ?
C7 N1 Sb1 C1 -11.1(2) . . . . ?
C8 N1 Sb1 C1 177.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_594r
_database_code_depnum_ccdc_archive 'CCDC 1020711'
_audit_update_record             
;
2015-04-04 deposited with the CCDC.
2015-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 F N2 Sb'
_chemical_formula_sum            'C18 H24 F N2 Sb'
_chemical_formula_weight         409.14

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1371(8)
_cell_length_b                   8.0760(7)
_cell_length_c                   24.949(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.549(2)
_cell_angle_gamma                90.00
_cell_volume                     1832.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5176
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.11
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    1.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6595
_exptl_absorpt_correction_T_max  0.7319
_exptl_absorpt_process_details   'Bruker, 2001.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16818
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3223
_reflns_number_gt                2982
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0215P)²+7.0226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3223
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_restrained_S_all      1.251
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2140(6) 0.3464(7) 0.0749(2) 0.0372(13) Uani 1 1 d . . .
C2 C 0.2037(6) 0.1767(8) 0.0819(2) 0.0400(14) Uani 1 1 d . . .
C3 C 0.3175(7) 0.0727(9) 0.0693(2) 0.0521(17) Uani 1 1 d . . .
H3 H 0.3086 -0.0414 0.0729 0.063 Uiso 1 1 calc R . .
C4 C 0.4422(7) 0.1389(10) 0.0518(3) 0.0568(18) Uani 1 1 d . . .
H4 H 0.5195 0.0700 0.0446 0.068 Uiso 1 1 calc R . .
C5 C 0.4532(8) 0.3050(11) 0.0449(3) 0.067(2) Uani 1 1 d . . .
H5 H 0.5379 0.3491 0.0326 0.081 Uiso 1 1 calc R . .
C6 C 0.3401(7) 0.4091(9) 0.0558(3) 0.0575(18) Uani 1 1 d . . .
H6 H 0.3486 0.5224 0.0502 0.069 Uiso 1 1 calc R . .
C7 C 0.0725(7) 0.1062(8) 0.1060(3) 0.0476(15) Uani 1 1 d . . .
H7A H 0.0526 -0.0045 0.0921 0.057 Uiso 1 1 calc R . .
H7B H 0.0936 0.0984 0.1448 0.057 Uiso 1 1 calc R . .
C8 C -0.1215(7) 0.1772(10) 0.0383(3) 0.0602(19) Uani 1 1 d . . .
H8A H -0.0491 0.1966 0.0135 0.090 Uiso 1 1 calc R . .
H8B H -0.2041 0.2490 0.0297 0.090 Uiso 1 1 calc R . .
H8C H -0.1533 0.0639 0.0356 0.090 Uiso 1 1 calc R . .
C9 C -0.1680(8) 0.1855(9) 0.1316(3) 0.0620(19) Uani 1 1 d . . .
H9A H -0.2454 0.2654 0.1249 0.093 Uiso 1 1 calc R . .
H9B H -0.1227 0.1988 0.1677 0.093 Uiso 1 1 calc R . .
H9C H -0.2081 0.0759 0.1273 0.093 Uiso 1 1 calc R . .
C10 C 0.0643(7) 0.4923(8) 0.1760(2) 0.0462(14) Uani 1 1 d . . .
C11 C -0.0278(7) 0.5884(8) 0.2057(3) 0.0490(16) Uani 1 1 d . . .
C12 C -0.0062(10) 0.5777(11) 0.2619(3) 0.073(2) Uani 1 1 d . . .
H12 H -0.0661 0.6401 0.2822 0.088 Uiso 1 1 calc R . .
C13 C 0.1005(10) 0.4783(12) 0.2884(3) 0.081(3) Uani 1 1 d . . .
H13 H 0.1097 0.4702 0.3258 0.098 Uiso 1 1 calc R . .
C14 C 0.1913(9) 0.3928(11) 0.2588(3) 0.073(2) Uani 1 1 d . . .
H14 H 0.2659 0.3281 0.2759 0.088 Uiso 1 1 calc R . .
C15 C 0.1743(8) 0.4006(9) 0.2035(3) 0.0564(17) Uani 1 1 d . . .
H15 H 0.2391 0.3420 0.1841 0.068 Uiso 1 1 calc R . .
C16 C -0.1428(8) 0.6985(8) 0.1778(3) 0.0588(18) Uani 1 1 d . . .
H16A H -0.1790 0.7726 0.2042 0.071 Uiso 1 1 calc R . .
H16B H -0.0978 0.7659 0.1517 0.071 Uiso 1 1 calc R . .
C17 C -0.3588(9) 0.5390(11) 0.1882(4) 0.087(3) Uani 1 1 d . . .
H17A H -0.3017 0.4651 0.2120 0.130 Uiso 1 1 calc R . .
H17B H -0.4378 0.4789 0.1689 0.130 Uiso 1 1 calc R . .
H17C H -0.3984 0.6258 0.2088 0.130 Uiso 1 1 calc R . .
C18 C -0.3498(10) 0.7177(10) 0.1122(4) 0.083(3) Uani 1 1 d . . .
H18A H -0.3750 0.8176 0.1300 0.125 Uiso 1 1 calc R . .
H18B H -0.4380 0.6623 0.0979 0.125 Uiso 1 1 calc R . .
H18C H -0.2914 0.7444 0.0834 0.125 Uiso 1 1 calc R . .
F1 F 0.1705(5) 0.7026(4) 0.09138(18) 0.0736(12) Uani 1 1 d . . .
N1 N -0.0573(5) 0.2108(6) 0.09323(19) 0.0414(12) Uani 1 1 d . . .
N2 N -0.2664(6) 0.6100(7) 0.1505(2) 0.0579(15) Uani 1 1 d . . .
Sb1 Sb 0.03428(5) 0.50340(6) 0.089489(16) 0.04575(16) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
C1 C2 1.386(8) . ?
C1 C6 1.386(8) . ?
C1 Sb1 2.134(6) . ?
C2 C3 1.396(9) . ?
C2 C7 1.504(8) . ?
C3 C4 1.368(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.465(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.463(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N1 1.473(8) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.378(9) . ?
C10 C11 1.408(9) . ?
C10 Sb1 2.150(6) . ?
C11 C12 1.399(10) . ?
C11 C16 1.496(9) . ?
C12 C13 1.381(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.354(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(10) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N2 1.450(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N2 1.442(9) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N2 1.452(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F1 Sb1 2.031(4) . ?
N1 Sb1 2.512(5) . ?

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
C2 C1 C6 118.3(6) . . ?
C2 C1 Sb1 120.2(4) . . ?
C6 C1 Sb1 121.4(5) . . ?
C1 C2 C3 120.3(6) . . ?
C1 C2 C7 119.4(5) . . ?
C3 C2 C7 120.2(6) . . ?
C4 C3 C2 119.9(7) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.1(7) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.7(7) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.6(7) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 C2 110.7(5) . . ?
N1 C7 H7A 109.5 . . ?
C2 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.5(6) . . ?
C15 C10 Sb1 122.6(5) . . ?
C11 C10 Sb1 118.8(5) . . ?
C12 C11 C10 117.5(7) . . ?
C12 C11 C16 121.8(7) . . ?
C10 C11 C16 120.7(6) . . ?
C13 C12 C11 122.7(8) . . ?
C13 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C14 C13 C12 118.4(7) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 120.7(8) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 122.1(7) . . ?
C14 C15 H15 118.9 . . ?
C10 C15 H15 118.9 . . ?
N2 C16 C11 113.9(6) . . ?
N2 C16 H16A 108.8 . . ?
C11 C16 H16A 108.8 . . ?
N2 C16 H16B 108.8 . . ?
C11 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 N1 C7 109.9(5) . . ?
C8 N1 C9 110.2(5) . . ?
C7 N1 C9 111.7(5) . . ?
C8 N1 Sb1 104.1(4) . . ?
C7 N1 Sb1 106.6(3) . . ?
C9 N1 Sb1 114.0(4) . . ?
C17 N2 C16 111.6(6) . . ?
C17 N2 C18 111.3(7) . . ?
C16 N2 C18 110.4(6) . . ?
F1 Sb1 C1 89.7(2) . . ?
F1 Sb1 C10 89.5(2) . . ?
C1 Sb1 C10 96.9(2) . . ?
F1 Sb1 N1 161.74(17) . . ?
C1 Sb1 N1 73.24(18) . . ?
C10 Sb1 N1 86.2(2) . . ?

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
C6 C1 C2 C3 -0.6(9) . . . . ?
Sb1 C1 C2 C3 176.2(4) . . . . ?
C6 C1 C2 C7 176.1(6) . . . . ?
Sb1 C1 C2 C7 -7.2(7) . . . . ?
C1 C2 C3 C4 2.3(9) . . . . ?
C7 C2 C3 C4 -174.3(6) . . . . ?
C2 C3 C4 C5 -2.3(10) . . . . ?
C3 C4 C5 C6 0.6(12) . . . . ?
C4 C5 C6 C1 1.1(12) . . . . ?
C2 C1 C6 C5 -1.1(10) . . . . ?
Sb1 C1 C6 C5 -177.8(5) . . . . ?
C1 C2 C7 N1 29.7(8) . . . . ?
C3 C2 C7 N1 -153.6(5) . . . . ?
C15 C10 C11 C12 -3.2(9) . . . . ?
Sb1 C10 C11 C12 179.6(5) . . . . ?
C15 C10 C11 C16 176.1(6) . . . . ?
Sb1 C10 C11 C16 -1.0(8) . . . . ?
C10 C11 C12 C13 0.2(11) . . . . ?
C16 C11 C12 C13 -179.2(7) . . . . ?
C11 C12 C13 C14 2.6(13) . . . . ?
C12 C13 C14 C15 -2.2(13) . . . . ?
C13 C14 C15 C10 -1.0(12) . . . . ?
C11 C10 C15 C14 3.8(10) . . . . ?
Sb1 C10 C15 C14 -179.2(6) . . . . ?
C12 C11 C16 N2 -109.1(7) . . . . ?
C10 C11 C16 N2 71.5(8) . . . . ?
C2 C7 N1 C8 79.4(6) . . . . ?
C2 C7 N1 C9 -158.0(5) . . . . ?
C2 C7 N1 Sb1 -32.9(5) . . . . ?
C11 C16 N2 C17 72.2(8) . . . . ?
C11 C16 N2 C18 -163.4(6) . . . . ?
C2 C1 Sb1 F1 164.3(5) . . . . ?
C6 C1 Sb1 F1 -19.0(5) . . . . ?
C2 C1 Sb1 C10 74.8(5) . . . . ?
C6 C1 Sb1 C10 -108.5(5) . . . . ?
C2 C1 Sb1 N1 -9.1(4) . . . . ?
C6 C1 Sb1 N1 167.6(5) . . . . ?
C15 C10 Sb1 F1 -90.2(5) . . . . ?
C11 C10 Sb1 F1 86.8(5) . . . . ?
C15 C10 Sb1 C1 -0.6(6) . . . . ?
C11 C10 Sb1 C1 176.5(5) . . . . ?
C15 C10 Sb1 N1 72.0(5) . . . . ?
C11 C10 Sb1 N1 -110.9(5) . . . . ?
C8 N1 Sb1 F1 -114.4(6) . . . . ?
C7 N1 Sb1 F1 1.7(7) . . . . ?
C9 N1 Sb1 F1 125.5(6) . . . . ?
C8 N1 Sb1 C1 -92.8(4) . . . . ?
C7 N1 Sb1 C1 23.3(4) . . . . ?
C9 N1 Sb1 C1 147.0(5) . . . . ?
C8 N1 Sb1 C10 168.8(4) . . . . ?
C7 N1 Sb1 C10 -75.1(4) . . . . ?
C9 N1 Sb1 C10 48.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.087
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_148alb
_database_code_depnum_ccdc_archive 'CCDC 1020712'
_audit_update_record             
;
2015-04-04 deposited with the CCDC.
2015-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 F N Sb'
_chemical_formula_sum            'C15 H17 F N Sb'
_chemical_formula_weight         352.05

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3139(8)
_cell_length_b                   8.1198(6)
_cell_length_c                   15.8500(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.4870(10)
_cell_angle_gamma                90.00
_cell_volume                     1426.92(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6261
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    1.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4776
_exptl_absorpt_correction_T_max  0.6049
_exptl_absorpt_process_details   'Bruker, 2001.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13223
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2516
_reflns_number_gt                2387
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0244P)²+1.3221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2516
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0645
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1990(3) 0.2226(4) 1.0352(2) 0.0394(7) Uani 1 1 d . . .
C2 C 0.2985(3) 0.1448(4) 1.0860(2) 0.0383(7) Uani 1 1 d . . .
C3 C 0.3430(3) 0.2013(4) 1.1688(2) 0.0497(8) Uani 1 1 d . . .
H3 H 0.4095 0.1501 1.2026 0.060 Uiso 1 1 calc R . .
C4 C 0.2892(4) 0.3332(5) 1.2014(2) 0.0614(10) Uani 1 1 d . . .
H4 H 0.3193 0.3701 1.2571 0.074 Uiso 1 1 calc R . .
C5 C 0.1914(4) 0.4098(5) 1.1518(3) 0.0604(10) Uani 1 1 d . . .
H5 H 0.1556 0.4988 1.1737 0.072 Uiso 1 1 calc R . .
C6 C 0.1464(3) 0.3548(4) 1.0695(3) 0.0528(9) Uani 1 1 d . . .
H6 H 0.0797 0.4069 1.0364 0.063 Uiso 1 1 calc R . .
C7 C 0.3577(3) 0.0059(4) 1.0474(2) 0.0429(7) Uani 1 1 d . . .
H7A H 0.4181 0.0500 1.0179 0.052 Uiso 1 1 calc R . .
H7B H 0.3979 -0.0663 1.0929 0.052 Uiso 1 1 calc R . .
C8 C 0.3305(4) -0.1976(5) 0.9343(3) 0.0615(10) Uani 1 1 d . . .
H8A H 0.3798 -0.1326 0.9043 0.092 Uiso 1 1 calc R . .
H8B H 0.2715 -0.2563 0.8934 0.092 Uiso 1 1 calc R . .
H8C H 0.3803 -0.2747 0.9713 0.092 Uiso 1 1 calc R . .
C9 C 0.1916(4) -0.1877(5) 1.0314(3) 0.0705(11) Uani 1 1 d . . .
H9A H 0.2403 -0.2654 1.0688 0.106 Uiso 1 1 calc R . .
H9B H 0.1329 -0.2458 0.9900 0.106 Uiso 1 1 calc R . .
H9C H 0.1511 -0.1165 1.0649 0.106 Uiso 1 1 calc R . .
C10 C 0.2886(3) 0.2094(4) 0.8573(2) 0.0435(7) Uani 1 1 d . . .
C11 C 0.3190(3) 0.1268(5) 0.7874(2) 0.0541(9) Uani 1 1 d . . .
H11 H 0.2735 0.0365 0.7638 0.065 Uiso 1 1 calc R . .
C12 C 0.4159(4) 0.1774(6) 0.7526(2) 0.0621(10) Uani 1 1 d . . .
H12 H 0.4355 0.1205 0.7063 0.075 Uiso 1 1 calc R . .
C13 C 0.4828(4) 0.3108(5) 0.7861(3) 0.0620(10) Uani 1 1 d . . .
H13 H 0.5476 0.3451 0.7624 0.074 Uiso 1 1 calc R . .
C14 C 0.4541(4) 0.3947(5) 0.8551(3) 0.0604(10) Uani 1 1 d . . .
H14 H 0.4996 0.4855 0.8779 0.073 Uiso 1 1 calc R . .
C15 C 0.3581(3) 0.3442(4) 0.8903(2) 0.0515(8) Uani 1 1 d . . .
H15 H 0.3396 0.4013 0.9369 0.062 Uiso 1 1 calc R . .
F1 F 0.0554(2) 0.3514(3) 0.87653(16) 0.0782(7) Uani 1 1 d . . .
N1 N 0.2690(2) -0.0887(3) 0.98644(18) 0.0448(6) Uani 1 1 d . . .
Sb1 Sb 0.134075(18) 0.13293(3) 0.907308(14) 0.04737(10) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
C1 C6 1.390(4) . ?
C1 C2 1.397(4) . ?
C1 Sb1 2.142(3) . ?
C2 C3 1.388(5) . ?
C2 C7 1.503(4) . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.464(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.475(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N1 1.474(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.387(5) . ?
C10 C11 1.396(5) . ?
C10 Sb1 2.150(3) . ?
C11 C12 1.384(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
F1 Sb1 2.001(2) . ?
N1 Sb1 2.526(3) . ?

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
C6 C1 C2 118.9(3) . . ?
C6 C1 Sb1 122.7(2) . . ?
C2 C1 Sb1 118.5(2) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 C7 121.7(3) . . ?
C1 C2 C7 118.6(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N1 C7 C2 111.1(2) . . ?
N1 C7 H7A 109.4 . . ?
C2 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C2 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 117.9(3) . . ?
C15 C10 Sb1 122.0(3) . . ?
C11 C10 Sb1 120.1(3) . . ?
C12 C11 C10 120.9(4) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 121.0(4) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C7 N1 C9 111.2(3) . . ?
C7 N1 C8 110.3(3) . . ?
C9 N1 C8 109.6(3) . . ?
C7 N1 Sb1 102.76(18) . . ?
C9 N1 Sb1 105.7(2) . . ?
C8 N1 Sb1 117.0(2) . . ?
F1 Sb1 C1 88.94(11) . . ?
F1 Sb1 C10 90.50(11) . . ?
C1 Sb1 C10 95.73(12) . . ?
F1 Sb1 N1 161.47(10) . . ?
C1 Sb1 N1 73.30(10) . . ?
C10 Sb1 N1 86.18(10) . . ?

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
C6 C1 C2 C3 -0.4(5) . . . . ?
Sb1 C1 C2 C3 179.5(2) . . . . ?
C6 C1 C2 C7 -177.8(3) . . . . ?
Sb1 C1 C2 C7 2.0(4) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C7 C2 C3 C4 177.6(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
Sb1 C1 C6 C5 -179.4(3) . . . . ?
C3 C2 C7 N1 149.0(3) . . . . ?
C1 C2 C7 N1 -33.6(4) . . . . ?
C15 C10 C11 C12 0.4(5) . . . . ?
Sb1 C10 C11 C12 178.0(3) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C14 0.4(6) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C13 C14 C15 C10 -0.2(5) . . . . ?
C11 C10 C15 C14 0.0(5) . . . . ?
Sb1 C10 C15 C14 -177.6(3) . . . . ?
C2 C7 N1 C9 -71.6(4) . . . . ?
C2 C7 N1 C8 166.5(3) . . . . ?
C2 C7 N1 Sb1 41.0(3) . . . . ?
C6 C1 Sb1 F1 21.4(3) . . . . ?
C2 C1 Sb1 F1 -158.5(2) . . . . ?
C6 C1 Sb1 C10 111.7(3) . . . . ?
C2 C1 Sb1 C10 -68.1(2) . . . . ?
C6 C1 Sb1 N1 -164.0(3) . . . . ?
C2 C1 Sb1 N1 16.1(2) . . . . ?
C15 C10 Sb1 F1 60.3(3) . . . . ?
C11 C10 Sb1 F1 -117.2(3) . . . . ?
C15 C10 Sb1 C1 -28.7(3) . . . . ?
C11 C10 Sb1 C1 153.8(3) . . . . ?
C15 C10 Sb1 N1 -101.5(3) . . . . ?
C11 C10 Sb1 N1 81.0(3) . . . . ?
C7 N1 Sb1 F1 -14.0(4) . . . . ?
C9 N1 Sb1 F1 102.7(4) . . . . ?
C8 N1 Sb1 F1 -135.0(3) . . . . ?
C7 N1 Sb1 C1 -31.05(19) . . . . ?
C9 N1 Sb1 C1 85.6(2) . . . . ?
C8 N1 Sb1 C1 -152.0(3) . . . . ?
C7 N1 Sb1 C10 66.1(2) . . . . ?
C9 N1 Sb1 C10 -177.2(2) . . . . ?
C8 N1 Sb1 C10 -54.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.068
