# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2sbi
_database_code_depnum_ccdc_archive 'CCDC 1859257'
loop_
_audit_author_name
_audit_author_address
'Jian Lei, Yongping Liu,  Yi Chen, Chak-Tong Au?  Shuang-Feng Yin'
;Hunan university
China
;
_audit_update_record             
;
2018-07-30 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 I N Sb'
_chemical_formula_sum            'C20 H23 I N Sb'
_chemical_formula_weight         526.04
_chemical_melting_point          ?
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   11.3664(3)
_cell_length_b                   12.5996(3)
_cell_length_c                   13.0792(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.703(2)
_cell_angle_gamma                90
_cell_volume                     1866.79(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7726
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3180
_cell_measurement_theta_min      2.4610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12759
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.248
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  58.00   1.00    1.00    --  -11.59  57.00   0.00   97
  2  ω    -14.00  78.00   1.00    1.00    --   11.74  77.00 120.00   92
  3  ω     50.00  77.00   1.00    1.00    --   11.74 178.00-150.00   27
  4  ω    -82.00  13.00   1.00    1.00    --  -11.59 -57.00-150.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0442735000
_diffrn_orient_matrix_UB_12      0.0040923000
_diffrn_orient_matrix_UB_13      0.0414231000
_diffrn_orient_matrix_UB_21      0.0328125000
_diffrn_orient_matrix_UB_22      0.0346329000
_diffrn_orient_matrix_UB_23      -0.0295936000
_diffrn_orient_matrix_UB_31      -0.0297282000
_diffrn_orient_matrix_UB_32      0.0441626000
_diffrn_orient_matrix_UB_33      0.0193156000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3011
_reflns_number_total             3284
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+0.6467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0540
_refine_ls_wR_factor_ref         0.0561
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C13(H13A,H13B), C18(H18A,H18B), C14(H14A,H14B), C19(H19A,
 H19B), C17(H17A,H17B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C2(H2), C5(H5), C9(H9), C3(H3), C10(H10), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Sb1 Sb 0.71666(2) 0.51547(2) 0.52816(2) 0.01156(8) Uani 1 1 d . . . . .
I1 I 0.74108(2) 0.73820(2) 0.45986(2) 0.01946(8) Uani 1 1 d . . . . .
N1 N 0.6996(2) 0.35954(18) 0.63129(19) 0.0111(5) Uani 1 1 d . . . . .
C12 C 0.5279(3) 0.4662(2) 0.6725(2) 0.0116(7) Uani 1 1 d . . . . .
C7 C 0.5777(3) 0.5538(2) 0.6259(2) 0.0137(7) Uani 1 1 d . . . . .
C6 C 0.8658(3) 0.5274(2) 0.6403(2) 0.0131(7) Uani 1 1 d . . . . .
C11 C 0.4376(3) 0.4795(2) 0.7362(3) 0.0148(7) Uani 1 1 d . . . . .
H11 H 0.406371 0.420926 0.767731 0.018 Uiso 1 1 calc R . . . .
C8 C 0.5311(3) 0.6547(2) 0.6428(2) 0.0143(7) Uani 1 1 d . . . . .
H8 H 0.561662 0.713597 0.611257 0.017 Uiso 1 1 calc R . . . .
C15 C 0.7328(3) 0.2634(2) 0.5709(3) 0.0134(7) Uani 1 1 d . . . . .
H15 H 0.687997 0.268314 0.503787 0.016 Uiso 1 1 calc R . . . .
C2 C 0.9726(3) 0.4494(2) 0.7885(3) 0.0149(7) Uani 1 1 d . . . . .
H2 H 0.977720 0.399068 0.840661 0.018 Uiso 1 1 calc R . . . .
C5 C 0.9580(3) 0.5998(2) 0.6339(3) 0.0149(7) Uani 1 1 d . . . . .
H5 H 0.953334 0.650738 0.582223 0.018 Uiso 1 1 calc R . . . .
C1 C 0.8740(3) 0.4514(2) 0.7185(2) 0.0115(7) Uani 1 1 d . . . . .
C9 C 0.4398(3) 0.6676(2) 0.7061(3) 0.0166(7) Uani 1 1 d . . . . .
H9 H 0.409575 0.734891 0.716978 0.020 Uiso 1 1 calc R . . . .
C16 C 0.8632(3) 0.2641(2) 0.5506(3) 0.0152(7) Uani 1 1 d . . . . .
H16A H 0.911314 0.256282 0.614894 0.018 Uiso 1 1 calc R . . . .
H16B H 0.882815 0.331464 0.520324 0.018 Uiso 1 1 calc R . . . .
C13 C 0.5721(3) 0.3564(2) 0.6500(2) 0.0128(7) Uani 1 1 d . . . . .
H13A H 0.560923 0.310024 0.707584 0.015 Uiso 1 1 calc R . . . .
H13B H 0.526938 0.327922 0.590043 0.015 Uiso 1 1 calc R . . . .
C18 C 0.8531(3) 0.0667(2) 0.5203(3) 0.0194(8) Uani 1 1 d . . . . .
H18A H 0.865163 0.011234 0.470733 0.023 Uiso 1 1 calc R . . . .
H18B H 0.902057 0.050665 0.582627 0.023 Uiso 1 1 calc R . . . .
C14 C 0.7728(3) 0.3753(2) 0.7293(2) 0.0120(7) Uani 1 1 d . . . . .
H14A H 0.804236 0.307304 0.753370 0.014 Uiso 1 1 calc R . . . .
H14B H 0.723486 0.402463 0.780467 0.014 Uiso 1 1 calc R . . . .
C3 C 1.0642(3) 0.5221(2) 0.7816(3) 0.0191(8) Uani 1 1 d . . . . .
H3 H 1.129829 0.520508 0.828915 0.023 Uiso 1 1 calc R . . . .
C10 C 0.3937(3) 0.5802(2) 0.7531(3) 0.0157(7) Uani 1 1 d . . . . .
H10 H 0.333195 0.588956 0.796038 0.019 Uiso 1 1 calc R . . . .
C19 C 0.7247(3) 0.0682(2) 0.5431(3) 0.0176(7) Uani 1 1 d . . . . .
H19A H 0.704511 0.000494 0.572469 0.021 Uiso 1 1 calc R . . . .
H19B H 0.675452 0.077643 0.479660 0.021 Uiso 1 1 calc R . . . .
C4 C 1.0566(3) 0.5963(2) 0.7040(3) 0.0193(8) Uani 1 1 d . . . . .
H4 H 1.117784 0.644451 0.698529 0.023 Uiso 1 1 calc R . . . .
C17 C 0.8902(3) 0.1733(2) 0.4778(3) 0.0200(8) Uani 1 1 d . . . . .
H17A H 0.848406 0.185228 0.411137 0.024 Uiso 1 1 calc R . . . .
H17B H 0.974145 0.172133 0.469004 0.024 Uiso 1 1 calc R . . . .
C20 C 0.6996(3) 0.1570(2) 0.6175(3) 0.0156(7) Uani 1 1 d . . . . .
H20A H 0.745316 0.146147 0.682583 0.019 Uiso 1 1 calc R . . . .
H20B H 0.616530 0.157016 0.629749 0.019 Uiso 1 1 calc R . . . .


_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
Sb1 I1 2.9649(3) . ?
Sb1 N1 2.400(2) . ?
Sb1 C7 2.167(3) . ?
Sb1 C6 2.154(3) . ?
N1 C15 1.510(4) . ?
N1 C13 1.490(4) . ?
N1 C14 1.484(4) . ?
C12 C7 1.402(4) . ?
C12 C11 1.385(4) . ?
C12 C13 1.508(4) . ?
C7 C8 1.401(4) . ?
C6 C5 1.397(4) . ?
C6 C1 1.399(4) . ?
C11 C10 1.387(4) . ?
C8 C9 1.390(4) . ?
C15 C16 1.527(4) . ?
C15 C20 1.533(4) . ?
C2 C1 1.388(4) . ?
C2 C3 1.395(4) . ?
C5 C4 1.389(5) . ?
C1 C14 1.513(4) . ?
C9 C10 1.384(4) . ?
C16 C17 1.535(4) . ?
C18 C19 1.514(4) . ?
C18 C17 1.527(4) . ?
C3 C4 1.377(5) . ?
C19 C20 1.526(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Sb1 I1 163.34(6) . . ?
C7 Sb1 I1 93.31(8) . . ?
C7 Sb1 N1 75.77(10) . . ?
C6 Sb1 I1 92.93(8) . . ?
C6 Sb1 N1 76.70(10) . . ?
C6 Sb1 C7 98.84(12) . . ?
C15 N1 Sb1 109.10(18) . . ?
C13 N1 Sb1 103.80(17) . . ?
C13 N1 C15 110.7(2) . . ?
C14 N1 Sb1 108.11(16) . . ?
C14 N1 C15 114.3(2) . . ?
C14 N1 C13 110.3(2) . . ?
C7 C12 C13 119.0(3) . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 C13 120.2(3) . . ?
C12 C7 Sb1 114.8(2) . . ?
C8 C7 Sb1 126.7(2) . . ?
C8 C7 C12 118.4(3) . . ?
C5 C6 Sb1 123.8(2) . . ?
C5 C6 C1 119.1(3) . . ?
C1 C6 Sb1 116.8(2) . . ?
C12 C11 C10 120.1(3) . . ?
C9 C8 C7 120.6(3) . . ?
N1 C15 C16 112.0(2) . . ?
N1 C15 C20 114.4(3) . . ?
C16 C15 C20 110.4(2) . . ?
C3 C2 C1 120.8(3) . . ?
C4 C5 C6 120.5(3) . . ?
C6 C1 C14 119.8(3) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 C14 120.4(3) . . ?
C10 C9 C8 119.9(3) . . ?
C15 C16 C17 110.5(3) . . ?
N1 C13 C12 110.6(2) . . ?
C19 C18 C17 111.1(3) . . ?
N1 C14 C1 112.4(2) . . ?
C4 C3 C2 119.4(3) . . ?
C11 C10 C9 120.2(3) . . ?
C18 C19 C20 111.7(3) . . ?
C3 C4 C5 120.4(3) . . ?
C18 C17 C16 110.8(3) . . ?
C19 C20 C15 108.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.916
####################################################################### 
# 
# 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_sb
_database_code_depnum_ccdc_archive 'CCDC 945752'
_audit_update_record             
;
2013-07-10 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 I N Sb'
_chemical_formula_sum            'C20 H17 I N Sb'
_chemical_formula_weight         520.00

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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.1637(3)
_cell_length_b                   10.9833(4)
_cell_length_c                   18.0957(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.7840(10)
_cell_angle_gamma                90.00
_cell_volume                     1812.02(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1051
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.64

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    3.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5439
_exptl_absorpt_correction_T_max  0.7870
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9043
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3510
_reflns_number_gt                3094
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0411P)²+0.3837P] 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     SHELXL
_refine_ls_extinction_coef       0.0046(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3510
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
Sb1 Sb 0.48435(2) 0.22415(2) 0.017117(12) 0.03837(12) Uani 1 1 d . . .
I1 I 0.75527(3) 0.26645(3) 0.110842(17) 0.05897(13) Uani 1 1 d . . .
N1 N 0.2223(3) 0.1859(2) -0.02929(13) 0.0358(6) Uani 1 1 d . . .
C1 C 0.3661(4) 0.3697(3) 0.06557(15) 0.0374(7) Uani 1 1 d . . .
C8 C 0.4129(4) 0.0796(3) 0.08736(17) 0.0412(7) Uani 1 1 d . . .
C2 C 0.4355(4) 0.4716(3) 0.09942(17) 0.0464(8) Uani 1 1 d . . .
H3A H 0.5373 0.4761 0.1048 0.056 Uiso 1 1 calc R . .
C3 C 0.3534(4) 0.5663(3) 0.12506(19) 0.0504(9) Uani 1 1 d . . .
H4A H 0.4000 0.6334 0.1481 0.060 Uiso 1 1 calc R . .
C4 C 0.2018(4) 0.5601(3) 0.11604(19) 0.0504(9) Uani 1 1 d . . .
H5A H 0.1465 0.6230 0.1334 0.061 Uiso 1 1 calc R . .
C5 C 0.1321(4) 0.4606(3) 0.08132(17) 0.0420(8) Uani 1 1 d . . .
H6A H 0.0302 0.4577 0.0746 0.050 Uiso 1 1 calc R . .
C6 C 0.2137(4) 0.3648(3) 0.05633(15) 0.0355(7) Uani 1 1 d . . .
C7 C 0.1339(4) 0.2549(3) 0.02186(18) 0.0379(7) Uani 1 1 d . . .
H8A H 0.1090 0.2008 0.0611 0.045 Uiso 1 1 calc R . .
H8B H 0.0430 0.2814 -0.0056 0.045 Uiso 1 1 calc R . .
C15 C 0.1926(4) 0.2264(3) -0.10623(18) 0.0399(8) Uani 1 1 d . . .
C20 C 0.2024(4) 0.3490(3) -0.12238(17) 0.0479(8) Uani 1 1 d . . .
H10A H 0.2268 0.4040 -0.0841 0.057 Uiso 1 1 calc R . .
C19 C 0.1764(5) 0.3911(4) -0.19465(19) 0.0612(10) Uani 1 1 d . . .
H11A H 0.1810 0.4740 -0.2047 0.073 Uiso 1 1 calc R . .
C18 C 0.1437(6) 0.3088(5) -0.2516(2) 0.0804(15) Uani 1 1 d . . .
H12A H 0.1289 0.3359 -0.3005 0.096 Uiso 1 1 calc R . .
C17 C 0.1332(8) 0.1898(5) -0.2363(2) 0.0932(18) Uani 1 1 d . . .
H13A H 0.1099 0.1357 -0.2753 0.112 Uiso 1 1 calc R . .
C16 C 0.1561(5) 0.1443(4) -0.1640(2) 0.0664(12) Uani 1 1 d . . .
H14A H 0.1473 0.0616 -0.1545 0.080 Uiso 1 1 calc R . .
C14 C 0.2154(4) 0.0530(3) -0.01832(17) 0.0400(7) Uani 1 1 d . . .
H15A H 0.2663 0.0120 -0.0557 0.048 Uiso 1 1 calc R . .
H15B H 0.1139 0.0266 -0.0240 0.048 Uiso 1 1 calc R . .
C13 C 0.2850(4) 0.0193(3) 0.05807(16) 0.0388(7) Uani 1 1 d . . .
C12 C 0.2268(4) -0.0742(3) 0.09765(19) 0.0469(8) Uani 1 1 d . . .
H17A H 0.1412 -0.1131 0.0783 0.056 Uiso 1 1 calc R . .
C11 C 0.2962(4) -0.1100(3) 0.16600(19) 0.0517(9) Uani 1 1 d . . .
H18A H 0.2568 -0.1722 0.1926 0.062 Uiso 1 1 calc R . .
C10 C 0.4234(5) -0.0531(4) 0.1941(2) 0.0589(10) Uani 1 1 d . . .
H19A H 0.4712 -0.0782 0.2393 0.071 Uiso 1 1 calc R . .
C9 C 0.4810(4) 0.0417(3) 0.15534(18) 0.0501(9) Uani 1 1 d . . .
H20A H 0.5664 0.0803 0.1753 0.060 Uiso 1 1 calc R . .


_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
Sb1 C1 2.165(3) . ?
Sb1 C8 2.176(3) . ?
Sb1 N1 2.498(3) . ?
Sb1 I1 2.8994(4) . ?
N1 C15 1.461(4) . ?
N1 C14 1.475(4) . ?
N1 C7 1.496(4) . ?
C1 C6 1.392(4) . ?
C1 C2 1.397(5) . ?
C8 C9 1.386(4) . ?
C8 C13 1.403(4) . ?
C2 C3 1.391(5) . ?
C2 H3A 0.9300 . ?
C3 C4 1.384(5) . ?
C3 H4A 0.9300 . ?
C4 C5 1.383(5) . ?
C4 H5A 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H6A 0.9300 . ?
C6 C7 1.513(4) . ?
C7 H8A 0.9700 . ?
C7 H8B 0.9700 . ?
C15 C20 1.382(5) . ?
C15 C16 1.395(5) . ?
C20 C19 1.385(4) . ?
C20 H10A 0.9300 . ?
C19 C18 1.381(6) . ?
C19 H11A 0.9300 . ?
C18 C17 1.341(7) . ?
C18 H12A 0.9300 . ?
C17 C16 1.398(6) . ?
C17 H13A 0.9300 . ?
C16 H14A 0.9300 . ?
C14 C13 1.509(4) . ?
C14 H15A 0.9700 . ?
C14 H15B 0.9700 . ?
C13 C12 1.389(4) . ?
C12 C11 1.389(5) . ?
C12 H17A 0.9300 . ?
C11 C10 1.374(6) . ?
C11 H18A 0.9300 . ?
C10 C9 1.389(5) . ?
C10 H19A 0.9300 . ?
C9 H20A 0.9300 . ?

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
C1 Sb1 C8 96.31(12) . . ?
C1 Sb1 N1 75.94(10) . . ?
C8 Sb1 N1 74.82(11) . . ?
C1 Sb1 I1 94.51(8) . . ?
C8 Sb1 I1 93.75(9) . . ?
N1 Sb1 I1 163.92(5) . . ?
C15 N1 C14 115.0(2) . . ?
C15 N1 C7 112.0(3) . . ?
C14 N1 C7 112.6(2) . . ?
C15 N1 Sb1 110.47(19) . . ?
C14 N1 Sb1 100.02(18) . . ?
C7 N1 Sb1 105.63(18) . . ?
C6 C1 C2 119.4(3) . . ?
C6 C1 Sb1 117.4(2) . . ?
C2 C1 Sb1 123.0(3) . . ?
C9 C8 C13 118.5(3) . . ?
C9 C8 Sb1 127.1(3) . . ?
C13 C8 Sb1 114.4(2) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H3A 119.7 . . ?
C1 C2 H3A 119.7 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H4A 120.2 . . ?
C2 C3 H4A 120.2 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H5A 119.9 . . ?
C3 C4 H5A 119.9 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H6A 119.8 . . ?
C6 C5 H6A 119.8 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 C7 121.2(3) . . ?
C5 C6 C7 119.0(3) . . ?
N1 C7 C6 112.9(3) . . ?
N1 C7 H8A 109.0 . . ?
C6 C7 H8A 109.0 . . ?
N1 C7 H8B 109.0 . . ?
C6 C7 H8B 109.0 . . ?
H8A C7 H8B 107.8 . . ?
C20 C15 C16 119.1(3) . . ?
C20 C15 N1 119.2(3) . . ?
C16 C15 N1 121.7(3) . . ?
C15 C20 C19 121.1(3) . . ?
C15 C20 H10A 119.5 . . ?
C19 C20 H10A 119.5 . . ?
C18 C19 C20 119.3(4) . . ?
C18 C19 H11A 120.3 . . ?
C20 C19 H11A 120.3 . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H12A 120.0 . . ?
C19 C18 H12A 120.0 . . ?
C18 C17 C16 122.3(4) . . ?
C18 C17 H13A 118.9 . . ?
C16 C17 H13A 118.9 . . ?
C15 C16 C17 118.2(4) . . ?
C15 C16 H14A 120.9 . . ?
C17 C16 H14A 120.9 . . ?
N1 C14 C13 110.3(2) . . ?
N1 C14 H15A 109.6 . . ?
C13 C14 H15A 109.6 . . ?
N1 C14 H15B 109.6 . . ?
C13 C14 H15B 109.6 . . ?
H15A C14 H15B 108.1 . . ?
C12 C13 C8 120.2(3) . . ?
C12 C13 C14 120.3(3) . . ?
C8 C13 C14 119.3(3) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H17A 119.9 . . ?
C11 C12 H17A 119.9 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H18A 120.1 . . ?
C12 C11 H18A 120.1 . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H19A 119.8 . . ?
C9 C10 H19A 119.8 . . ?
C8 C9 C10 120.9(4) . . ?
C8 C9 H20A 119.6 . . ?
C10 C9 H20A 119.6 . . ?

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
C1 Sb1 N1 C15 102.3(2) . . . . ?
C8 Sb1 N1 C15 -157.0(2) . . . . ?
I1 Sb1 N1 C15 157.12(17) . . . . ?
C1 Sb1 N1 C14 -136.08(19) . . . . ?
C8 Sb1 N1 C14 -35.40(18) . . . . ?
I1 Sb1 N1 C14 -81.3(3) . . . . ?
C1 Sb1 N1 C7 -19.06(19) . . . . ?
C8 Sb1 N1 C7 81.63(19) . . . . ?
I1 Sb1 N1 C7 35.8(3) . . . . ?
C8 Sb1 C1 C6 -65.5(2) . . . . ?
N1 Sb1 C1 C6 7.1(2) . . . . ?
I1 Sb1 C1 C6 -159.8(2) . . . . ?
C8 Sb1 C1 C2 120.2(3) . . . . ?
N1 Sb1 C1 C2 -167.2(3) . . . . ?
I1 Sb1 C1 C2 25.9(3) . . . . ?
C1 Sb1 C8 C9 -89.6(3) . . . . ?
N1 Sb1 C8 C9 -163.2(3) . . . . ?
I1 Sb1 C8 C9 5.3(3) . . . . ?
C1 Sb1 C8 C13 91.4(2) . . . . ?
N1 Sb1 C8 C13 17.9(2) . . . . ?
I1 Sb1 C8 C13 -173.6(2) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
Sb1 C1 C2 C3 175.5(2) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
Sb1 C1 C6 C5 -175.1(2) . . . . ?
C2 C1 C6 C7 -178.3(3) . . . . ?
Sb1 C1 C6 C7 7.1(4) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C4 C5 C6 C7 177.2(3) . . . . ?
C15 N1 C7 C6 -92.7(3) . . . . ?
C14 N1 C7 C6 135.8(3) . . . . ?
Sb1 N1 C7 C6 27.7(3) . . . . ?
C1 C6 C7 N1 -26.0(4) . . . . ?
C5 C6 C7 N1 156.1(3) . . . . ?
C14 N1 C15 C20 -177.4(3) . . . . ?
C7 N1 C15 C20 52.3(4) . . . . ?
Sb1 N1 C15 C20 -65.1(3) . . . . ?
C14 N1 C15 C16 1.9(5) . . . . ?
C7 N1 C15 C16 -128.3(4) . . . . ?
Sb1 N1 C15 C16 114.2(4) . . . . ?
C16 C15 C20 C19 0.1(6) . . . . ?
N1 C15 C20 C19 179.4(3) . . . . ?
C15 C20 C19 C18 -1.5(6) . . . . ?
C20 C19 C18 C17 1.9(8) . . . . ?
C19 C18 C17 C16 -0.8(9) . . . . ?
C20 C15 C16 C17 1.0(7) . . . . ?
N1 C15 C16 C17 -178.3(4) . . . . ?
C18 C17 C16 C15 -0.7(9) . . . . ?
C15 N1 C14 C13 165.3(3) . . . . ?
C7 N1 C14 C13 -64.7(3) . . . . ?
Sb1 N1 C14 C13 47.0(3) . . . . ?
C9 C8 C13 C12 1.5(5) . . . . ?
Sb1 C8 C13 C12 -179.4(2) . . . . ?
C9 C8 C13 C14 -175.6(3) . . . . ?
Sb1 C8 C13 C14 3.4(4) . . . . ?
N1 C14 C13 C12 143.4(3) . . . . ?
N1 C14 C13 C8 -39.5(4) . . . . ?
C8 C13 C12 C11 -1.0(5) . . . . ?
C14 C13 C12 C11 176.1(3) . . . . ?
C13 C12 C11 C10 -0.5(5) . . . . ?
C12 C11 C10 C9 1.4(6) . . . . ?
C13 C8 C9 C10 -0.6(5) . . . . ?
Sb1 C8 C9 C10 -179.5(3) . . . . ?
C11 C10 C9 C8 -0.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.133
####################################################################### 
# 
# 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_cd201108
_database_code_depnum_ccdc_archive 'CCDC 769426'
_audit_update_record             
;
2013-06-26 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 F N Sb'
_chemical_formula_weight         412.10

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

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                   10.2974(8)
_cell_length_b                   10.3031(8)
_cell_length_c                   15.7161(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.5590(10)
_cell_angle_gamma                90.00
_cell_volume                     1633.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5604
_cell_measurement_theta_min      4.757
_cell_measurement_theta_max      56.409

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    1.697
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7205
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            9422
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3560
_reflns_number_gt                3240
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0452P)²+0.2193P] 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     SHELXL
_refine_ls_extinction_coef       0.0027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3560
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_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
Sb Sb 0.653365(18) 1.033072(18) 0.956625(11) 0.03461(10) Uani 1 1 d . . .
F1 F 0.65776(19) 1.21170(19) 1.00662(13) 0.0554(5) Uani 1 1 d . . .
N1 N 0.6519(2) 0.8617(2) 0.84182(15) 0.0357(5) Uani 1 1 d . . .
C1 C 0.8281(3) 1.0685(3) 0.90699(18) 0.0335(6) Uani 1 1 d . . .
C2 C 0.9296(3) 1.1485(3) 0.94954(19) 0.0400(6) Uani 1 1 d . . .
H2 H 0.9183 1.1949 0.9983 0.048 Uiso 1 1 calc R . .
C3 C 1.0462(3) 1.1596(3) 0.9202(2) 0.0478(7) Uani 1 1 d . . .
H3 H 1.1132 1.2135 0.9491 0.057 Uiso 1 1 calc R . .
C4 C 1.0641(3) 1.0909(4) 0.8479(2) 0.0527(8) Uani 1 1 d . . .
H4 H 1.1432 1.0976 0.8283 0.063 Uiso 1 1 calc R . .
C5 C 0.9635(4) 1.0122(3) 0.8052(2) 0.0469(8) Uani 1 1 d . . .
H5 H 0.9749 0.9670 0.7560 0.056 Uiso 1 1 calc R . .
C6 C 0.8462(3) 0.9996(3) 0.83424(19) 0.0367(6) Uani 1 1 d . . .
C7 C 0.7345(3) 0.9192(3) 0.78480(18) 0.0401(6) Uani 1 1 d . . .
H7A H 0.6793 0.9732 0.7415 0.048 Uiso 1 1 calc R . .
H7B H 0.7708 0.8502 0.7546 0.048 Uiso 1 1 calc R . .
C8 C 0.5076(3) 1.0919(3) 0.84513(18) 0.0364(6) Uani 1 1 d . . .
C9 C 0.4561(3) 1.2167(3) 0.8332(2) 0.0436(7) Uani 1 1 d . . .
H9 H 0.4854 1.2806 0.8745 0.052 Uiso 1 1 calc R . .
C10 C 0.3610(3) 1.2464(3) 0.7599(2) 0.0543(9) Uani 1 1 d . . .
H10 H 0.3266 1.3300 0.7527 0.065 Uiso 1 1 calc R . .
C11 C 0.3173(3) 1.1546(4) 0.6983(2) 0.0514(8) Uani 1 1 d . . .
H11 H 0.2551 1.1761 0.6488 0.062 Uiso 1 1 calc R . .
C12 C 0.3661(3) 1.0293(3) 0.7099(2) 0.0462(8) Uani 1 1 d . . .
H12 H 0.3360 0.9662 0.6683 0.055 Uiso 1 1 calc R . .
C13 C 0.4599(3) 0.9977(3) 0.7835(2) 0.0385(6) Uani 1 1 d . . .
C14 C 0.5103(3) 0.8601(3) 0.7971(2) 0.0464(7) Uani 1 1 d . . .
H14A H 0.4584 0.8129 0.8320 0.056 Uiso 1 1 calc R . .
H14B H 0.5013 0.8166 0.7415 0.056 Uiso 1 1 calc R . .
C15 C 0.6995(3) 0.7405(3) 0.88211(18) 0.0356(6) Uani 1 1 d . . .
C16 C 0.6248(3) 0.6774(3) 0.9341(2) 0.0469(7) Uani 1 1 d . . .
H16 H 0.5454 0.7133 0.9422 0.056 Uiso 1 1 calc R . .
C17 C 0.6689(4) 0.5610(4) 0.9738(3) 0.0556(9) Uani 1 1 d . . .
H17 H 0.6174 0.5186 1.0074 0.067 Uiso 1 1 calc R . .
C18 C 0.7865(4) 0.5072(3) 0.9645(2) 0.0504(8) Uani 1 1 d . . .
H18 H 0.8141 0.4279 0.9902 0.060 Uiso 1 1 calc R . .
C19 C 0.8630(3) 0.5725(3) 0.9166(2) 0.0460(7) Uani 1 1 d . . .
H19 H 0.9448 0.5385 0.9116 0.055 Uiso 1 1 calc R . .
C20 C 0.8202(3) 0.6887(3) 0.87517(18) 0.0398(6) Uani 1 1 d . . .
H20 H 0.8733 0.7315 0.8427 0.048 Uiso 1 1 calc R . .


_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
Sb F1 1.9981(18) . ?
Sb C1 2.131(3) . ?
Sb C8 2.154(3) . ?
Sb N1 2.522(2) . ?
N1 C15 1.441(3) . ?
N1 C7 1.477(4) . ?
N1 C14 1.486(4) . ?
C1 C6 1.390(4) . ?
C1 C2 1.392(4) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.389(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.389(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.510(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.378(4) . ?
C15 C16 1.390(4) . ?
C16 C17 1.386(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
F1 Sb C1 91.84(10) . . ?
F1 Sb C8 91.03(10) . . ?
C1 Sb C8 98.99(10) . . ?
F1 Sb N1 157.29(8) . . ?
C1 Sb N1 75.07(10) . . ?
C8 Sb N1 73.25(9) . . ?
C15 N1 C7 115.3(2) . . ?
C15 N1 C14 114.4(2) . . ?
C7 N1 C14 110.3(2) . . ?
C15 N1 Sb 109.85(16) . . ?
C7 N1 Sb 103.40(16) . . ?
C14 N1 Sb 102.14(17) . . ?
C6 C1 C2 119.1(3) . . ?
C6 C1 Sb 118.4(2) . . ?
C2 C1 Sb 122.2(2) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 120.8(3) . . ?
C1 C6 C7 119.5(3) . . ?
N1 C7 C6 112.4(2) . . ?
N1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C13 C8 C9 118.8(3) . . ?
C13 C8 Sb 117.5(2) . . ?
C9 C8 Sb 123.7(2) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 120.4(3) . . ?
C8 C13 C14 119.6(3) . . ?
C12 C13 C14 120.0(3) . . ?
N1 C14 C13 109.5(2) . . ?
N1 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
N1 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C20 C15 C16 118.6(3) . . ?
C20 C15 N1 122.3(3) . . ?
C16 C15 N1 119.0(3) . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 118.6(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C20 121.1(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C19 120.2(3) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?

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
F1 Sb N1 C15 156.6(2) . . . . ?
C1 Sb N1 C15 100.09(19) . . . . ?
C8 Sb N1 C15 -155.5(2) . . . . ?
F1 Sb N1 C7 33.0(3) . . . . ?
C1 Sb N1 C7 -23.52(17) . . . . ?
C8 Sb N1 C7 80.90(18) . . . . ?
F1 Sb N1 C14 -81.6(3) . . . . ?
C1 Sb N1 C14 -138.13(19) . . . . ?
C8 Sb N1 C14 -33.71(18) . . . . ?
F1 Sb C1 C6 -152.9(2) . . . . ?
C8 Sb C1 C6 -61.6(2) . . . . ?
N1 Sb C1 C6 8.3(2) . . . . ?
F1 Sb C1 C2 33.3(2) . . . . ?
C8 Sb C1 C2 124.6(2) . . . . ?
N1 Sb C1 C2 -165.5(2) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
Sb C1 C2 C3 173.8(2) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C4 C5 C6 C7 176.8(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
Sb C1 C6 C5 -174.4(2) . . . . ?
C2 C1 C6 C7 -176.4(3) . . . . ?
Sb C1 C6 C7 9.6(3) . . . . ?
C15 N1 C7 C6 -85.2(3) . . . . ?
C14 N1 C7 C6 143.3(2) . . . . ?
Sb N1 C7 C6 34.7(3) . . . . ?
C5 C6 C7 N1 150.5(3) . . . . ?
C1 C6 C7 N1 -33.5(4) . . . . ?
F1 Sb C8 C13 -178.1(2) . . . . ?
C1 Sb C8 C13 89.9(2) . . . . ?
N1 Sb C8 C13 18.6(2) . . . . ?
F1 Sb C8 C9 -0.3(2) . . . . ?
C1 Sb C8 C9 -92.3(3) . . . . ?
N1 Sb C8 C9 -163.6(3) . . . . ?
C13 C8 C9 C10 -1.4(4) . . . . ?
Sb C8 C9 C10 -179.2(2) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C9 C10 C11 C12 1.5(5) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C9 C8 C13 C12 2.4(4) . . . . ?
Sb C8 C13 C12 -179.7(2) . . . . ?
C9 C8 C13 C14 -177.5(3) . . . . ?
Sb C8 C13 C14 0.4(4) . . . . ?
C11 C12 C13 C8 -1.4(5) . . . . ?
C11 C12 C13 C14 178.4(3) . . . . ?
C15 N1 C14 C13 161.7(2) . . . . ?
C7 N1 C14 C13 -66.4(3) . . . . ?
Sb N1 C14 C13 43.1(3) . . . . ?
C8 C13 C14 N1 -34.2(4) . . . . ?
C12 C13 C14 N1 146.0(3) . . . . ?
C7 N1 C15 C20 6.4(4) . . . . ?
C14 N1 C15 C20 136.0(3) . . . . ?
Sb N1 C15 C20 -109.9(3) . . . . ?
C7 N1 C15 C16 -177.5(3) . . . . ?
C14 N1 C15 C16 -48.0(4) . . . . ?
Sb N1 C15 C16 66.1(3) . . . . ?
C20 C15 C16 C17 -3.6(5) . . . . ?
N1 C15 C16 C17 -179.7(3) . . . . ?
C15 C16 C17 C18 1.4(6) . . . . ?
C16 C17 C18 C19 1.7(6) . . . . ?
C17 C18 C19 C20 -2.5(6) . . . . ?
C16 C15 C20 C19 2.8(4) . . . . ?
N1 C15 C20 C19 178.8(3) . . . . ?
C18 C19 C20 C15 0.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.166
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_3sbf
_database_code_depnum_ccdc_archive 'CCDC 1859365'
loop_
_audit_author_name
_audit_author_address
'Jian Lei, Yongping Liu, Yi Chen, Chak-Tong Au?Shuang-Feng Yin'
;Hunan university
China
;
_audit_update_record             
;
2018-07-31 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 F N Sb'
_chemical_formula_sum            'C20 H23 F N Sb'
_chemical_formula_weight         418.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   9.3503(3)
_cell_length_b                   15.9263(5)
_cell_length_c                   11.7239(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.044(3)
_cell_angle_gamma                90
_cell_volume                     1693.69(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6028
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.2420
_cell_measurement_theta_min      2.8100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.638
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10827
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.200
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  19.00   1.00    1.00    --  -11.59 -77.00 -60.00   95
  2  ω    -57.00  35.00   1.00    1.00    --   11.74 -57.00  60.00   92
  3  ω    -15.00  81.00   1.00    1.00    --   11.74  57.00-150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0714598000
_diffrn_orient_matrix_UB_12      -0.0136303000
_diffrn_orient_matrix_UB_13      0.0022608000
_diffrn_orient_matrix_UB_21      -0.0028306000
_diffrn_orient_matrix_UB_22      -0.0264169000
_diffrn_orient_matrix_UB_23      -0.0492763000
_diffrn_orient_matrix_UB_31      0.0315681000
_diffrn_orient_matrix_UB_32      -0.0331360000
_diffrn_orient_matrix_UB_33      0.0382420000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2682
_reflns_number_total             2984
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0242P)²+0.3515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
_refine_ls_wR_factor_ref         0.0598
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C19(H19A,H19B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C9(H9), C8(H8), C10(H10), C4(H4), C5(H5), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Sb1 Sb 0.12668(2) 0.76938(2) 0.49513(2) 0.01203(8) Uani 1 1 d . . . . .
F1 F 0.11307(17) 0.87863(11) 0.40637(12) 0.0200(4) Uani 1 1 d . . . . .
N1 N 0.2067(2) 0.67430(15) 0.66281(17) 0.0104(5) Uani 1 1 d . . . . .
C6 C 0.3614(3) 0.78249(19) 0.5443(2) 0.0120(6) Uani 1 1 d . . . . .
C7 C 0.0758(3) 0.83630(18) 0.6391(2) 0.0110(6) Uani 1 1 d . . . . .
C1 C 0.4398(3) 0.72115(18) 0.6203(2) 0.0117(6) Uani 1 1 d . . . . .
C20 C -0.0530(3) 0.62663(19) 0.6526(2) 0.0138(6) Uani 1 1 d . . . . .
H20A H -0.054094 0.647931 0.729897 0.017 Uiso 1 1 calc R . . . .
H20B H -0.086206 0.671113 0.595829 0.017 Uiso 1 1 calc R . . . .
C2 C 0.5915(3) 0.72884(18) 0.6627(2) 0.0127(6) Uani 1 1 d . . . . .
H2 H 0.643035 0.689359 0.715414 0.015 Uiso 1 1 calc R . . . .
C12 C 0.1187(3) 0.80021(19) 0.7511(2) 0.0121(6) Uani 1 1 d . . . . .
C11 C 0.0780(3) 0.83815(19) 0.8456(2) 0.0156(7) Uani 1 1 d . . . . .
H11 H 0.105491 0.814060 0.919958 0.019 Uiso 1 1 calc R . . . .
C9 C -0.0462(3) 0.9480(2) 0.7182(2) 0.0167(7) Uani 1 1 d . . . . .
H9 H -0.101083 0.997341 0.707081 0.020 Uiso 1 1 calc R . . . .
C19 C -0.1571(3) 0.55149(19) 0.6230(2) 0.0149(6) Uani 1 1 d . . . . .
H19A H -0.254935 0.568091 0.628682 0.018 Uiso 1 1 calc R . . . .
H19B H -0.163515 0.534123 0.542573 0.018 Uiso 1 1 calc R . . . .
C15 C 0.1044(3) 0.60047(18) 0.6506(2) 0.0116(6) Uani 1 1 d . . . . .
H15 H 0.098104 0.577249 0.572167 0.014 Uiso 1 1 calc R . . . .
C14 C 0.3567(3) 0.64748(18) 0.6532(2) 0.0128(6) Uani 1 1 d . . . . .
H14A H 0.347437 0.603958 0.593945 0.015 Uiso 1 1 calc R . . . .
H14B H 0.411022 0.624434 0.727722 0.015 Uiso 1 1 calc R . . . .
C16 C 0.1576(3) 0.52857(19) 0.7374(2) 0.0140(6) Uani 1 1 d . . . . .
H16A H 0.256070 0.511755 0.733533 0.017 Uiso 1 1 calc R . . . .
H16B H 0.162068 0.547597 0.816751 0.017 Uiso 1 1 calc R . . . .
C17 C 0.0538(3) 0.45378(19) 0.7085(2) 0.0155(6) Uani 1 1 d . . . . .
H17A H 0.058333 0.431025 0.632663 0.019 Uiso 1 1 calc R . . . .
H17B H 0.085968 0.410334 0.767064 0.019 Uiso 1 1 calc R . . . .
C18 C -0.1048(3) 0.4778(2) 0.7052(2) 0.0183(7) Uani 1 1 d . . . . .
H18A H -0.112110 0.492486 0.783864 0.022 Uiso 1 1 calc R . . . .
H18B H -0.168396 0.429865 0.679302 0.022 Uiso 1 1 calc R . . . .
C8 C -0.0062(3) 0.91013(19) 0.6240(2) 0.0145(6) Uani 1 1 d . . . . .
H8 H -0.034609 0.934377 0.549737 0.017 Uiso 1 1 calc R . . . .
C10 C -0.0040(3) 0.91223(19) 0.8286(2) 0.0171(7) Uani 1 1 d . . . . .
H10 H -0.030451 0.937635 0.891957 0.021 Uiso 1 1 calc R . . . .
C4 C 0.5896(3) 0.8543(2) 0.5489(2) 0.0168(7) Uani 1 1 d . . . . .
H4 H 0.640343 0.898175 0.524145 0.020 Uiso 1 1 calc R . . . .
C5 C 0.4377(3) 0.84833(19) 0.5078(2) 0.0145(6) Uani 1 1 d . . . . .
H5 H 0.386777 0.888362 0.455671 0.017 Uiso 1 1 calc R . . . .
C3 C 0.6659(3) 0.7949(2) 0.6270(2) 0.0173(7) Uani 1 1 d . . . . .
H3 H 0.767526 0.799574 0.655340 0.021 Uiso 1 1 calc R . . . .
C13 C 0.2175(3) 0.72404(17) 0.7717(2) 0.0114(6) Uani 1 1 d . . . . .
H13A H 0.318824 0.741939 0.801912 0.014 Uiso 1 1 calc R . . . .
H13B H 0.190917 0.688705 0.830706 0.014 Uiso 1 1 calc R . . . .


_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
Sb1 F1 2.0155(16) . ?
Sb1 N1 2.450(2) . ?
Sb1 C6 2.140(3) . ?
Sb1 C7 2.145(3) . ?
N1 C15 1.500(3) . ?
N1 C14 1.497(3) . ?
N1 C13 1.485(3) . ?
C6 C1 1.403(4) . ?
C6 C5 1.393(4) . ?
C7 C12 1.399(4) . ?
C7 C8 1.391(4) . ?
C1 C2 1.390(4) . ?
C1 C14 1.508(4) . ?
C20 C19 1.528(4) . ?
C20 C15 1.536(4) . ?
C2 C3 1.382(4) . ?
C12 C11 1.394(4) . ?
C12 C13 1.508(4) . ?
C11 C10 1.395(4) . ?
C9 C8 1.387(4) . ?
C9 C10 1.382(4) . ?
C19 C18 1.523(4) . ?
C15 C16 1.532(4) . ?
C16 C17 1.522(4) . ?
C17 C18 1.523(4) . ?
C4 C5 1.388(4) . ?
C4 C3 1.387(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 Sb1 N1 156.42(7) . . ?
F1 Sb1 C6 89.26(9) . . ?
F1 Sb1 C7 88.81(9) . . ?
C6 Sb1 N1 75.56(9) . . ?
C6 Sb1 C7 98.53(10) . . ?
C7 Sb1 N1 76.02(9) . . ?
C15 N1 Sb1 110.16(14) . . ?
C14 N1 Sb1 103.01(14) . . ?
C14 N1 C15 110.9(2) . . ?
C13 N1 Sb1 107.69(16) . . ?
C13 N1 C15 114.1(2) . . ?
C13 N1 C14 110.3(2) . . ?
C1 C6 Sb1 116.5(2) . . ?
C5 C6 Sb1 124.0(2) . . ?
C5 C6 C1 119.5(3) . . ?
C12 C7 Sb1 117.8(2) . . ?
C12 C7 C8 119.4(3) . . ?
C8 C7 Sb1 122.67(19) . . ?
C6 C1 C14 118.8(2) . . ?
C2 C1 C6 119.8(3) . . ?
C2 C1 C14 121.4(3) . . ?
C19 C20 C15 110.1(2) . . ?
C3 C2 C1 120.3(3) . . ?
C7 C12 C11 119.7(3) . . ?
C7 C12 C13 120.4(2) . . ?
C11 C12 C13 119.7(2) . . ?
C12 C11 C10 120.0(3) . . ?
C10 C9 C8 119.7(3) . . ?
C18 C19 C20 111.8(2) . . ?
N1 C15 C20 112.2(2) . . ?
N1 C15 C16 115.2(2) . . ?
C16 C15 C20 110.6(2) . . ?
N1 C14 C1 110.3(2) . . ?
C17 C16 C15 110.5(2) . . ?
C18 C17 C16 111.9(2) . . ?
C17 C18 C19 111.8(2) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C10 C11 120.3(3) . . ?
C3 C4 C5 120.1(3) . . ?
C4 C5 C6 120.1(3) . . ?
C2 C3 C4 120.2(3) . . ?
N1 C13 C12 112.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.829
####################################################################### 
# 
# 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_5hao
_database_code_depnum_ccdc_archive 'CCDC 1859366'
loop_
_audit_author_name
_audit_author_address
'Jian Lei, Yongping Liu,  Yi Chen, Chak-Tong Au?  Shuang-Feng Yin'
;Hunan university
China
;
_audit_update_record             
;
2018-07-31 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 I N Sb'
_chemical_formula_sum            'C18 H21 I N Sb'
_chemical_formula_weight         500.01
_chemical_melting_point          ?
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.3974(4)
_cell_length_b                   9.4136(3)
_cell_length_c                   14.8803(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.218(3)
_cell_angle_gamma                90
_cell_volume                     1735.29(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6282
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      29.2960
_cell_measurement_theta_min      2.5440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11089
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.561
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  10.00   1.00    1.00    --  -11.59 -57.00   0.00   87
  2  ω    -40.00  62.00   1.00    1.00    --  -11.59  57.00 150.00  102
  3  ω    -18.00  79.00   1.00    1.00    --   11.74  77.00 -90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0095376000
_diffrn_orient_matrix_UB_12      -0.0337258000
_diffrn_orient_matrix_UB_13      0.0422011000
_diffrn_orient_matrix_UB_21      -0.0406986000
_diffrn_orient_matrix_UB_22      -0.0506426000
_diffrn_orient_matrix_UB_23      -0.0112596000
_diffrn_orient_matrix_UB_31      0.0391403000
_diffrn_orient_matrix_UB_32      -0.0443791000
_diffrn_orient_matrix_UB_33      -0.0192258000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2773
_reflns_number_total             3058
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0179P)²+1.0577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0516
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C5(H5), C3(H3), C8(H8), C4(H4), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Sb1 Sb 0.73653(2) 0.48947(2) 0.50826(2) 0.01255(8) Uani 1 1 d . . . . .
I1 I 0.75661(2) 0.75731(2) 0.60997(2) 0.02020(8) Uani 1 1 d . . . . .
N1 N 0.7156(2) 0.2375(3) 0.46673(19) 0.0128(6) Uani 1 1 d . . . . .
C6 C 0.6004(2) 0.4153(3) 0.5822(2) 0.0120(7) Uani 1 1 d . . . . .
C7 C 0.8619(2) 0.3854(3) 0.5883(2) 0.0123(7) Uani 1 1 d . . . . .
C1 C 0.5526(2) 0.2902(3) 0.5496(2) 0.0144(7) Uani 1 1 d . . . . .
C2 C 0.4646(2) 0.2319(4) 0.5924(3) 0.0183(8) Uani 1 1 d . . . . .
H2 H 0.433036 0.148526 0.570550 0.022 Uiso 1 1 calc R . . . .
C11 C 0.9473(2) 0.1625(4) 0.6280(2) 0.0182(8) Uani 1 1 d . . . . .
H11 H 0.946720 0.063739 0.627637 0.022 Uiso 1 1 calc R . . . .
C14 C 0.5958(2) 0.2182(3) 0.4677(2) 0.0143(7) Uani 1 1 d . . . . .
H14A H 0.578563 0.117706 0.468884 0.017 Uiso 1 1 calc R . . . .
H14B H 0.562256 0.258873 0.413635 0.017 Uiso 1 1 calc R . . . .
C5 C 0.5580(2) 0.4811(3) 0.6572(2) 0.0154(7) Uani 1 1 d . . . . .
H5 H 0.587805 0.565837 0.678562 0.018 Uiso 1 1 calc R . . . .
C15 C 0.7616(2) 0.1963(4) 0.3758(2) 0.0152(7) Uani 1 1 d . . . . .
C16 C 0.7159(3) 0.2951(4) 0.3017(2) 0.0202(8) Uani 1 1 d . . . . .
H16A H 0.639897 0.278137 0.292648 0.030 Uiso 1 1 calc GR . . . .
H16B H 0.751648 0.276872 0.246824 0.030 Uiso 1 1 calc GR . . . .
H16C H 0.727543 0.392166 0.319372 0.030 Uiso 1 1 calc GR . . . .
C12 C 0.8621(2) 0.2370(3) 0.5866(2) 0.0128(7) Uani 1 1 d . . . . .
C3 C 0.4243(2) 0.2973(4) 0.6672(2) 0.0182(8) Uani 1 1 d . . . . .
H3 H 0.365523 0.258179 0.695211 0.022 Uiso 1 1 calc R . . . .
C8 C 0.9483(2) 0.4568(4) 0.6312(2) 0.0162(7) Uani 1 1 d . . . . .
H8 H 0.948699 0.555607 0.632699 0.019 Uiso 1 1 calc R . . . .
C18 C 0.8842(2) 0.2138(4) 0.3827(3) 0.0206(8) Uani 1 1 d . . . . .
H18A H 0.901753 0.308100 0.403056 0.031 Uiso 1 1 calc GR . . . .
H18B H 0.913572 0.198390 0.324791 0.031 Uiso 1 1 calc GR . . . .
H18C H 0.914331 0.145856 0.424786 0.031 Uiso 1 1 calc GR . . . .
C17 C 0.7334(3) 0.0425(4) 0.3503(2) 0.0192(8) Uani 1 1 d . . . . .
H17A H 0.761171 -0.020323 0.396501 0.029 Uiso 1 1 calc GR . . . .
H17B H 0.765057 0.019193 0.294335 0.029 Uiso 1 1 calc GR . . . .
H17C H 0.656441 0.032306 0.344252 0.029 Uiso 1 1 calc GR . . . .
C4 C 0.4710(2) 0.4203(4) 0.7003(2) 0.0180(8) Uani 1 1 d . . . . .
H4 H 0.444703 0.462956 0.751366 0.022 Uiso 1 1 calc R . . . .
C13 C 0.7676(2) 0.1583(3) 0.5428(2) 0.0134(7) Uani 1 1 d . . . . .
H13A H 0.792401 0.067184 0.521167 0.016 Uiso 1 1 calc R . . . .
H13B H 0.714417 0.140205 0.587544 0.016 Uiso 1 1 calc R . . . .
C10 C 1.0332(3) 0.2345(4) 0.6698(2) 0.0219(8) Uani 1 1 d . . . . .
H10 H 1.090481 0.184169 0.696501 0.026 Uiso 1 1 calc R . . . .
C9 C 1.0333(3) 0.3817(4) 0.6715(3) 0.0218(8) Uani 1 1 d . . . . .
H9 H 1.090441 0.430131 0.699808 0.026 Uiso 1 1 calc R . . . .


_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
Sb1 I1 2.9463(3) . ?
Sb1 N1 2.463(3) . ?
Sb1 C6 2.166(3) . ?
Sb1 C7 2.157(3) . ?
N1 C14 1.497(4) . ?
N1 C15 1.538(4) . ?
N1 C13 1.482(4) . ?
C6 C1 1.397(5) . ?
C6 C5 1.396(5) . ?
C7 C12 1.397(4) . ?
C7 C8 1.398(4) . ?
C1 C2 1.396(5) . ?
C1 C14 1.510(5) . ?
C2 C3 1.382(5) . ?
C11 C12 1.392(4) . ?
C11 C10 1.389(5) . ?
C5 C4 1.398(5) . ?
C15 C16 1.533(5) . ?
C15 C18 1.529(4) . ?
C15 C17 1.534(5) . ?
C12 C13 1.512(4) . ?
C3 C4 1.377(5) . ?
C8 C9 1.387(5) . ?
C10 C9 1.385(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
N1 Sb1 I1 163.59(7) . . ?
C6 Sb1 I1 93.83(9) . . ?
C6 Sb1 N1 74.95(10) . . ?
C7 Sb1 I1 93.47(9) . . ?
C7 Sb1 N1 76.55(11) . . ?
C7 Sb1 C6 97.59(11) . . ?
C14 N1 Sb1 102.08(17) . . ?
C14 N1 C15 112.3(2) . . ?
C15 N1 Sb1 115.11(18) . . ?
C13 N1 Sb1 104.75(18) . . ?
C13 N1 C14 109.5(2) . . ?
C13 N1 C15 112.4(2) . . ?
C1 C6 Sb1 115.1(2) . . ?
C1 C6 C5 119.0(3) . . ?
C5 C6 Sb1 126.0(2) . . ?
C12 C7 Sb1 116.5(2) . . ?
C12 C7 C8 119.2(3) . . ?
C8 C7 Sb1 123.8(2) . . ?
C6 C1 C2 120.1(3) . . ?
C6 C1 C14 120.0(3) . . ?
C2 C1 C14 120.0(3) . . ?
C3 C2 C1 120.3(3) . . ?
C10 C11 C12 120.6(3) . . ?
N1 C14 C1 109.7(3) . . ?
C6 C5 C4 120.4(3) . . ?
C16 C15 N1 109.9(3) . . ?
C16 C15 C17 108.7(3) . . ?
C18 C15 N1 108.3(3) . . ?
C18 C15 C16 108.8(3) . . ?
C18 C15 C17 109.5(3) . . ?
C17 C15 N1 111.5(3) . . ?
C7 C12 C13 119.8(3) . . ?
C11 C12 C7 119.8(3) . . ?
C11 C12 C13 120.4(3) . . ?
C4 C3 C2 120.2(3) . . ?
C9 C8 C7 120.5(3) . . ?
C3 C4 C5 120.1(3) . . ?
N1 C13 C12 112.9(3) . . ?
C9 C10 C11 119.7(3) . . ?
C10 C9 C8 120.2(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.233
_oxdiff_exptl_absorpt_empirical_full_min 0.824
####################################################################### 
# 
# 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_sb_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 945750'
_audit_update_record             
;
2013-07-10 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 Br N Sb'
_chemical_formula_sum            'C20 H17 Br N Sb'
_chemical_formula_weight         473.01

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'
Br Br -0.2901 2.4595 '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   'P 21/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                   9.5744(3)
_cell_length_b                   10.2962(3)
_cell_length_c                   18.1939(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.7950(10)
_cell_angle_gamma                90.00
_cell_volume                     1761.81(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1307
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      26.88

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    3.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5519
_exptl_absorpt_correction_T_max  0.8140
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10613
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3417
_reflns_number_gt                3059
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0312P)²+0.9817P] 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         3417
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0684
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Sb1 Sb 0.39215(2) 0.513873(18) 0.164462(11) 0.03668(9) Uani 1 1 d . . .
Br1 Br 0.23866(4) 0.72117(4) 0.11259(2) 0.06033(13) Uani 1 1 d . . .
N1 N 0.5856(3) 0.3711(2) 0.22690(13) 0.0359(5) Uani 1 1 d . . .
C8 C 0.5721(3) 0.5699(3) 0.11596(16) 0.0372(6) Uani 1 1 d . . .
C1 C 0.4557(3) 0.5911(3) 0.27599(16) 0.0372(6) Uani 1 1 d . . .
C2 C 0.4185(3) 0.7137(3) 0.29950(19) 0.0448(7) Uani 1 1 d . . .
H3A H 0.3746 0.7735 0.2643 0.054 Uiso 1 1 calc R . .
C3 C 0.4463(4) 0.7467(3) 0.3747(2) 0.0523(8) Uani 1 1 d . . .
H4A H 0.4205 0.8282 0.3898 0.063 Uiso 1 1 calc R . .
C4 C 0.5122(4) 0.6591(4) 0.4272(2) 0.0559(9) Uani 1 1 d . . .
H5A H 0.5301 0.6811 0.4777 0.067 Uiso 1 1 calc R . .
C5 C 0.5516(4) 0.5385(4) 0.40478(19) 0.0487(8) Uani 1 1 d . . .
H6A H 0.5958 0.4796 0.4405 0.058 Uiso 1 1 calc R . .
C6 C 0.5258(3) 0.5037(3) 0.32941(18) 0.0394(7) Uani 1 1 d . . .
C7 C 0.5701(4) 0.3714(3) 0.30714(17) 0.0446(7) Uani 1 1 d . . .
H8A H 0.6598 0.3475 0.3385 0.053 Uiso 1 1 calc R . .
H8B H 0.4994 0.3077 0.3146 0.053 Uiso 1 1 calc R . .
C15 C 0.5603(3) 0.2472(3) 0.18864(17) 0.0377(6) Uani 1 1 d . . .
C20 C 0.4480(4) 0.1699(3) 0.2006(2) 0.0527(9) Uani 1 1 d . . .
H10A H 0.3937 0.1953 0.2355 0.063 Uiso 1 1 calc R . .
C19 C 0.4158(4) 0.0546(4) 0.1609(2) 0.0585(9) Uani 1 1 d . . .
H11A H 0.3422 0.0022 0.1706 0.070 Uiso 1 1 calc R . .
C18 C 0.4924(4) 0.0182(3) 0.1076(2) 0.0595(10) Uani 1 1 d . . .
H12A H 0.4706 -0.0584 0.0809 0.071 Uiso 1 1 calc R . .
C17 C 0.6007(4) 0.0954(3) 0.0942(2) 0.0549(9) Uani 1 1 d . . .
H13A H 0.6516 0.0712 0.0575 0.066 Uiso 1 1 calc R . .
C16 C 0.6365(3) 0.2099(3) 0.13433(18) 0.0440(7) Uani 1 1 d . . .
H14A H 0.7112 0.2610 0.1248 0.053 Uiso 1 1 calc R . .
C14 C 0.7192(3) 0.4392(3) 0.21876(17) 0.0405(7) Uani 1 1 d . . .
H15A H 0.7939 0.3754 0.2192 0.049 Uiso 1 1 calc R . .
H15B H 0.7479 0.4964 0.2612 0.049 Uiso 1 1 calc R . .
C13 C 0.7031(3) 0.5177(3) 0.14758(18) 0.0381(7) Uani 1 1 d . . .
C12 C 0.8205(4) 0.5433(3) 0.1154(2) 0.0497(8) Uani 1 1 d . . .
H17A H 0.9085 0.5084 0.1365 0.060 Uiso 1 1 calc R . .
C11 C 0.8083(4) 0.6201(3) 0.0523(2) 0.0561(9) Uani 1 1 d . . .
H18A H 0.8878 0.6365 0.0312 0.067 Uiso 1 1 calc R . .
C10 C 0.6790(4) 0.6724(3) 0.02063(19) 0.0544(9) Uani 1 1 d . . .
H19A H 0.6710 0.7243 -0.0218 0.065 Uiso 1 1 calc R . .
C9 C 0.5596(4) 0.6474(3) 0.05215(18) 0.0468(8) Uani 1 1 d . . .
H20A H 0.4719 0.6823 0.0307 0.056 Uiso 1 1 calc R . .


_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
Sb1 C8 2.156(3) . ?
Sb1 C1 2.158(3) . ?
Sb1 N1 2.469(2) . ?
Sb1 Br1 2.6620(4) . ?
N1 C15 1.452(4) . ?
N1 C14 1.490(4) . ?
N1 C7 1.495(4) . ?
C8 C13 1.387(4) . ?
C8 C9 1.395(4) . ?
C1 C2 1.400(4) . ?
C1 C6 1.401(4) . ?
C2 C3 1.387(5) . ?
C2 H3A 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H4A 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H5A 0.9300 . ?
C5 C6 1.394(5) . ?
C5 H6A 0.9300 . ?
C6 C7 1.504(4) . ?
C7 H8A 0.9700 . ?
C7 H8B 0.9700 . ?
C15 C20 1.387(4) . ?
C15 C16 1.388(4) . ?
C20 C19 1.394(5) . ?
C20 H10A 0.9300 . ?
C19 C18 1.373(5) . ?
C19 H11A 0.9300 . ?
C18 C17 1.365(5) . ?
C18 H12A 0.9300 . ?
C17 C16 1.395(5) . ?
C17 H13A 0.9300 . ?
C16 H14A 0.9300 . ?
C14 C13 1.510(4) . ?
C14 H15A 0.9700 . ?
C14 H15B 0.9700 . ?
C13 C12 1.388(4) . ?
C12 C11 1.380(5) . ?
C12 H17A 0.9300 . ?
C11 C10 1.374(5) . ?
C11 H18A 0.9300 . ?
C10 C9 1.395(5) . ?
C10 H19A 0.9300 . ?
C9 H20A 0.9300 . ?

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
C8 Sb1 C1 100.36(10) . . ?
C8 Sb1 N1 76.09(10) . . ?
C1 Sb1 N1 74.43(10) . . ?
C8 Sb1 Br1 94.04(8) . . ?
C1 Sb1 Br1 94.45(8) . . ?
N1 Sb1 Br1 163.21(6) . . ?
C15 N1 C14 115.8(2) . . ?
C15 N1 C7 115.6(2) . . ?
C14 N1 C7 109.9(2) . . ?
C15 N1 Sb1 105.01(18) . . ?
C14 N1 Sb1 104.97(16) . . ?
C7 N1 Sb1 104.17(17) . . ?
C13 C8 C9 119.8(3) . . ?
C13 C8 Sb1 117.1(2) . . ?
C9 C8 Sb1 122.9(2) . . ?
C2 C1 C6 118.9(3) . . ?
C2 C1 Sb1 125.2(2) . . ?
C6 C1 Sb1 115.5(2) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H3A 119.7 . . ?
C1 C2 H3A 119.7 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H4A 119.9 . . ?
C2 C3 H4A 119.9 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H5A 120.0 . . ?
C5 C4 H5A 120.0 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H6A 119.5 . . ?
C6 C5 H6A 119.5 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 C7 119.4(3) . . ?
C1 C6 C7 121.2(3) . . ?
N1 C7 C6 110.5(2) . . ?
N1 C7 H8A 109.6 . . ?
C6 C7 H8A 109.6 . . ?
N1 C7 H8B 109.6 . . ?
C6 C7 H8B 109.6 . . ?
H8A C7 H8B 108.1 . . ?
C20 C15 C16 118.7(3) . . ?
C20 C15 N1 119.6(3) . . ?
C16 C15 N1 121.4(3) . . ?
C15 C20 C19 120.7(3) . . ?
C15 C20 H10A 119.7 . . ?
C19 C20 H10A 119.7 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H11A 119.9 . . ?
C20 C19 H11A 119.9 . . ?
C17 C18 C19 119.5(3) . . ?
C17 C18 H12A 120.2 . . ?
C19 C18 H12A 120.2 . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H13A 119.4 . . ?
C16 C17 H13A 119.4 . . ?
C15 C16 C17 119.7(3) . . ?
C15 C16 H14A 120.1 . . ?
C17 C16 H14A 120.1 . . ?
N1 C14 C13 112.7(2) . . ?
N1 C14 H15A 109.1 . . ?
C13 C14 H15A 109.1 . . ?
N1 C14 H15B 109.1 . . ?
C13 C14 H15B 109.1 . . ?
H15A C14 H15B 107.8 . . ?
C8 C13 C12 119.5(3) . . ?
C8 C13 C14 120.2(3) . . ?
C12 C13 C14 120.2(3) . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H17A 119.6 . . ?
C13 C12 H17A 119.6 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H18A 119.9 . . ?
C12 C11 H18A 119.9 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H19A 120.1 . . ?
C9 C10 H19A 120.1 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H20A 120.0 . . ?
C8 C9 H20A 120.0 . . ?

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
C8 Sb1 N1 C15 -100.83(18) . . . . ?
C1 Sb1 N1 C15 154.02(19) . . . . ?
Br1 Sb1 N1 C15 -156.12(15) . . . . ?
C8 Sb1 N1 C14 21.73(17) . . . . ?
C1 Sb1 N1 C14 -83.42(17) . . . . ?
Br1 Sb1 N1 C14 -33.6(3) . . . . ?
C8 Sb1 N1 C7 137.27(19) . . . . ?
C1 Sb1 N1 C7 32.12(18) . . . . ?
Br1 Sb1 N1 C7 82.0(2) . . . . ?
C1 Sb1 C8 C13 62.6(2) . . . . ?
N1 Sb1 C8 C13 -8.3(2) . . . . ?
Br1 Sb1 C8 C13 157.9(2) . . . . ?
C1 Sb1 C8 C9 -122.1(2) . . . . ?
N1 Sb1 C8 C9 166.9(3) . . . . ?
Br1 Sb1 C8 C9 -26.8(2) . . . . ?
C8 Sb1 C1 C2 93.5(3) . . . . ?
N1 Sb1 C1 C2 165.7(3) . . . . ?
Br1 Sb1 C1 C2 -1.5(2) . . . . ?
C8 Sb1 C1 C6 -94.1(2) . . . . ?
N1 Sb1 C1 C6 -21.8(2) . . . . ?
Br1 Sb1 C1 C6 171.0(2) . . . . ?
C6 C1 C2 C3 -2.0(4) . . . . ?
Sb1 C1 C2 C3 170.2(2) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C1 -1.7(5) . . . . ?
C4 C5 C6 C7 -179.9(3) . . . . ?
C2 C1 C6 C5 2.6(4) . . . . ?
Sb1 C1 C6 C5 -170.3(2) . . . . ?
C2 C1 C6 C7 -179.2(3) . . . . ?
Sb1 C1 C6 C7 7.9(4) . . . . ?
C15 N1 C7 C6 -151.6(3) . . . . ?
C14 N1 C7 C6 75.0(3) . . . . ?
Sb1 N1 C7 C6 -37.0(3) . . . . ?
C5 C6 C7 N1 -158.2(3) . . . . ?
C1 C6 C7 N1 23.6(4) . . . . ?
C14 N1 C15 C20 172.1(3) . . . . ?
C7 N1 C15 C20 41.5(4) . . . . ?
Sb1 N1 C15 C20 -72.6(3) . . . . ?
C14 N1 C15 C16 -14.7(4) . . . . ?
C7 N1 C15 C16 -145.3(3) . . . . ?
Sb1 N1 C15 C16 100.6(3) . . . . ?
C16 C15 C20 C19 2.4(5) . . . . ?
N1 C15 C20 C19 175.8(3) . . . . ?
C15 C20 C19 C18 -2.1(6) . . . . ?
C20 C19 C18 C17 0.4(6) . . . . ?
C19 C18 C17 C16 0.9(6) . . . . ?
C20 C15 C16 C17 -1.1(5) . . . . ?
N1 C15 C16 C17 -174.4(3) . . . . ?
C18 C17 C16 C15 -0.6(5) . . . . ?
C15 N1 C14 C13 83.8(3) . . . . ?
C7 N1 C14 C13 -143.0(2) . . . . ?
Sb1 N1 C14 C13 -31.5(3) . . . . ?
C9 C8 C13 C12 0.1(4) . . . . ?
Sb1 C8 C13 C12 175.6(2) . . . . ?
C9 C8 C13 C14 177.0(3) . . . . ?
Sb1 C8 C13 C14 -7.6(4) . . . . ?
N1 C14 C13 C8 29.2(4) . . . . ?
N1 C14 C13 C12 -154.0(3) . . . . ?
C8 C13 C12 C11 0.0(5) . . . . ?
C14 C13 C12 C11 -176.9(3) . . . . ?
C13 C12 C11 C10 0.1(5) . . . . ?
C12 C11 C10 C9 -0.2(5) . . . . ?
C11 C10 C9 C8 0.3(5) . . . . ?
C13 C8 C9 C10 -0.3(5) . . . . ?
Sb1 C8 C9 C10 -175.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1864560'
loop_
_audit_author_name
_audit_author_address
'Jian Lei, Yongping Liu,  Yi Chen, Chak-Tong Au?  Shuang-Feng Yin'
;Hunan university
China
;
_audit_update_record             
;
2018-08-29 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-08-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 Br N Sb'
_chemical_formula_sum            'C20 H23 Br N Sb'
_chemical_formula_weight         479.05
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.2338(5)
_cell_length_b                   16.5885(7)
_cell_length_c                   12.0033(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.346(2)
_cell_angle_gamma                90
_cell_volume                     1870.89(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3711
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.692
_shelx_estimated_absorpt_T_min   0.651
_exptl_absorpt_coefficient_mu    3.610
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6053
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1338 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.8117.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30234
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_min         2.219
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4079
_reflns_number_total             4636
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.00034(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4636
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0196
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0103P)²+1.3946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0384
_refine_ls_wR_factor_ref         0.0416
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C16(H16A,H16B), C20(H20A,H20B), C19(H19A,H19B),
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C14(H14), C2(H2), C4(H4), C3(H3), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Sb1 Sb 0.62678(2) 0.46405(2) 0.38740(2) 0.01570(4) Uani 1 1 d . . . . .
Br1 Br 0.58119(2) 0.30256(2) 0.37903(2) 0.02420(6) Uani 1 1 d . . . . .
N1 N 0.61728(18) 0.60364(9) 0.33645(15) 0.0166(3) Uani 1 1 d . . . . .
C9 C 0.3711(2) 0.57350(11) 0.30989(17) 0.0183(4) Uani 1 1 d . . . . .
C10 C 0.4024(2) 0.49147(12) 0.31407(17) 0.0185(4) Uani 1 1 d . . . . .
C6 C 0.6603(2) 0.46218(11) 0.22212(17) 0.0169(4) Uani 1 1 d . . . . .
C8 C 0.4910(2) 0.63365(11) 0.35659(18) 0.0190(4) Uani 1 1 d . . . . .
H8A H 0.460069 0.684688 0.315003 0.023 Uiso 1 1 calc R . . . .
H8B H 0.516844 0.642536 0.442594 0.023 Uiso 1 1 calc R . . . .
C7 C 0.5924(2) 0.60906(11) 0.20603(17) 0.0184(4) Uani 1 1 d . . . . .
H7A H 0.638493 0.657115 0.192987 0.022 Uiso 1 1 calc R . . . .
H7B H 0.491082 0.614062 0.157943 0.022 Uiso 1 1 calc R . . . .
C1 C 0.6487(2) 0.53629(11) 0.16379(17) 0.0173(4) Uani 1 1 d . . . . .
C5 C 0.7057(2) 0.39478(12) 0.17750(18) 0.0225(4) Uani 1 1 d . . . . .
H5 H 0.712777 0.345029 0.215175 0.027 Uiso 1 1 calc R . . . .
C11 C 0.2911(2) 0.43575(13) 0.27767(19) 0.0231(4) Uani 1 1 d . . . . .
H11 H 0.310915 0.380884 0.280690 0.028 Uiso 1 1 calc R . . . .
C14 C 0.2305(2) 0.59895(13) 0.26839(19) 0.0235(4) Uani 1 1 d . . . . .
H14 H 0.209927 0.653735 0.264937 0.028 Uiso 1 1 calc R . . . .
C16 C 0.8812(2) 0.61406(12) 0.4022(2) 0.0240(4) Uani 1 1 d . . . . .
H16A H 0.872455 0.628200 0.321140 0.029 Uiso 1 1 calc R . . . .
H16B H 0.886126 0.555782 0.409257 0.029 Uiso 1 1 calc R . . . .
C15 C 0.7511(2) 0.64421(11) 0.42124(18) 0.0195(4) Uani 1 1 d . . . . .
H15 H 0.764038 0.628658 0.503734 0.023 Uiso 1 1 calc R . . . .
C2 C 0.6827(2) 0.54218(13) 0.06251(18) 0.0224(4) Uani 1 1 d . . . . .
H2 H 0.673991 0.591433 0.023181 0.027 Uiso 1 1 calc R . . . .
C4 C 0.7403(2) 0.40173(13) 0.07711(19) 0.0269(5) Uani 1 1 d . . . . .
H4 H 0.770869 0.356683 0.048031 0.032 Uiso 1 1 calc R . . . .
C3 C 0.7293(2) 0.47534(14) 0.02031(19) 0.0261(5) Uani 1 1 d . . . . .
H3 H 0.753370 0.479873 -0.046456 0.031 Uiso 1 1 calc R . . . .
C20 C 0.7443(2) 0.73628(12) 0.4162(2) 0.0295(5) Uani 1 1 d . . . . .
H20A H 0.663715 0.754606 0.432684 0.035 Uiso 1 1 calc R . . . .
H20B H 0.730771 0.754319 0.335521 0.035 Uiso 1 1 calc R . . . .
C12 C 0.1513(2) 0.46173(14) 0.2371(2) 0.0290(5) Uani 1 1 d . . . . .
H12 H 0.077626 0.424270 0.213079 0.035 Uiso 1 1 calc R . . . .
C13 C 0.1208(2) 0.54325(14) 0.2321(2) 0.0287(5) Uani 1 1 d . . . . .
H13 H 0.026768 0.560578 0.204530 0.034 Uiso 1 1 calc R . . . .
C19 C 0.8812(3) 0.77290(14) 0.5093(2) 0.0372(6) Uani 1 1 d . . . . .
H19A H 0.876642 0.831147 0.501585 0.045 Uiso 1 1 calc R . . . .
H19B H 0.889434 0.759316 0.590370 0.045 Uiso 1 1 calc R . . . .
C17 C 1.0175(2) 0.65073(13) 0.4953(2) 0.0327(5) Uani 1 1 d . . . . .
H17A H 1.031095 0.632252 0.575845 0.039 Uiso 1 1 calc R . . . .
H17B H 1.098212 0.632663 0.478777 0.039 Uiso 1 1 calc R . . . .
C18 C 1.0113(3) 0.74245(13) 0.4917(2) 0.0368(6) Uani 1 1 d . . . . .
H18A H 1.096401 0.764088 0.555083 0.044 Uiso 1 1 calc R . . . .
H18B H 1.008517 0.761200 0.414231 0.044 Uiso 1 1 calc R . . . .


_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
Sb1 Br1 2.7142(2) . ?
Sb1 N1 2.3871(15) . ?
Sb1 C10 2.157(2) . ?
Sb1 C6 2.1433(18) . ?
N1 C8 1.491(2) . ?
N1 C7 1.486(2) . ?
N1 C15 1.503(3) . ?
C9 C10 1.394(3) . ?
C9 C8 1.507(3) . ?
C9 C14 1.389(3) . ?
C10 C11 1.396(3) . ?
C6 C1 1.396(3) . ?
C6 C5 1.396(3) . ?
C7 C1 1.509(3) . ?
C1 C2 1.395(3) . ?
C5 C4 1.389(3) . ?
C11 C12 1.385(3) . ?
C14 C13 1.385(3) . ?
C16 C15 1.522(3) . ?
C16 C17 1.526(3) . ?
C15 C20 1.529(3) . ?
C2 C3 1.380(3) . ?
C4 C3 1.381(3) . ?
C20 C19 1.529(3) . ?
C12 C13 1.384(3) . ?
C19 C18 1.515(3) . ?
C17 C18 1.523(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
N1 Sb1 Br1 163.53(4) . . ?
C10 Sb1 Br1 93.06(5) . . ?
C10 Sb1 N1 76.24(6) . . ?
C6 Sb1 Br1 92.27(5) . . ?
C6 Sb1 N1 77.41(6) . . ?
C6 Sb1 C10 99.22(7) . . ?
C8 N1 Sb1 103.43(11) . . ?
C8 N1 C15 110.85(15) . . ?
C7 N1 Sb1 107.53(11) . . ?
C7 N1 C8 110.67(15) . . ?
C7 N1 C15 114.59(15) . . ?
C15 N1 Sb1 109.10(11) . . ?
C10 C9 C8 119.40(18) . . ?
C14 C9 C10 120.04(19) . . ?
C14 C9 C8 120.49(17) . . ?
C9 C10 Sb1 114.40(14) . . ?
C9 C10 C11 119.15(19) . . ?
C11 C10 Sb1 126.37(15) . . ?
C1 C6 Sb1 116.00(13) . . ?
C5 C6 Sb1 124.48(14) . . ?
C5 C6 C1 119.20(18) . . ?
N1 C8 C9 110.42(15) . . ?
N1 C7 C1 112.12(15) . . ?
C6 C1 C7 120.26(17) . . ?
C2 C1 C6 119.85(18) . . ?
C2 C1 C7 119.81(17) . . ?
C4 C5 C6 120.28(19) . . ?
C12 C11 C10 120.4(2) . . ?
C13 C14 C9 120.4(2) . . ?
C15 C16 C17 111.06(18) . . ?
N1 C15 C16 111.56(16) . . ?
N1 C15 C20 113.95(16) . . ?
C16 C15 C20 110.54(17) . . ?
C3 C2 C1 120.38(19) . . ?
C3 C4 C5 120.19(19) . . ?
C2 C3 C4 120.09(19) . . ?
C15 C20 C19 110.74(18) . . ?
C13 C12 C11 120.2(2) . . ?
C12 C13 C14 119.8(2) . . ?
C18 C19 C20 111.6(2) . . ?
C18 C17 C16 111.19(19) . . ?
C19 C18 C17 111.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1861311'
loop_
_audit_author_name
_audit_author_address
'Jian Lei, Yongping Liu,  Yi Chen, Chak-Tong Au?  Shuang-Feng Yin'
;Hunan university
China
;
_audit_update_record             
;
2018-08-10 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-08-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 Br N Sb'
_chemical_formula_sum            'C18 H21 Br N Sb'
_chemical_formula_weight         453.02
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   9.8178(4)
_cell_length_b                   16.1278(5)
_cell_length_c                   11.4078(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.8950(10)
_cell_angle_gamma                90
_cell_volume                     1698.50(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4138
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.586
_cell_measurement_theta_min      2.950
_shelx_estimated_absorpt_T_max   0.669
_shelx_estimated_absorpt_T_min   0.626
_exptl_absorpt_coefficient_mu    3.970
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1503 before and 0.0692 after correction.
The Ratio of minimum to maximum transmission is 0.7877.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            49645
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.542
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2892
_reflns_number_total             2987
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0143
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0276P)²+0.5806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0537
_refine_ls_wR_factor_ref         0.0541
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C2(H2), C11(H11), C9(H9), C4(H4), C10(H10), C3(H3)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Sb1 Sb 0.25418(2) 0.51510(2) 0.58968(2) 0.01612(7) Uani 1 1 d . . . . .
Br1 Br 0.18727(2) 0.67822(2) 0.59179(2) 0.02468(8) Uani 1 1 d . . . . .
N1 N 0.31947(19) 0.37139(11) 0.65235(16) 0.0165(4) Uani 1 1 d . . . . .
C6 C 0.1080(2) 0.47881(13) 0.6847(2) 0.0180(5) Uani 1 1 d . . . . .
C1 C 0.0963(2) 0.39376(14) 0.6998(2) 0.0194(5) Uani 1 1 d . . . . .
C8 C 0.5138(2) 0.60372(14) 0.7947(2) 0.0220(5) Uani 1 1 d . . . . .
H8 H 0.478336 0.652127 0.750577 0.026 Uiso 1 1 calc R . . . .
C5 C 0.0286(2) 0.53309(15) 0.7313(2) 0.0221(5) Uani 1 1 d . . . . .
H5 H 0.035983 0.589970 0.721430 0.027 Uiso 1 1 calc R . . . .
C7 C 0.4419(2) 0.52911(13) 0.7546(2) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.4955(2) 0.45649(14) 0.8211(2) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.0062(3) 0.36397(15) 0.7619(2) 0.0249(5) Uani 1 1 d . . . . .
H2 H -0.000928 0.307195 0.772849 0.030 Uiso 1 1 calc R . . . .
C14 C 0.1774(2) 0.33438(14) 0.6452(2) 0.0199(5) Uani 1 1 d . . . . .
H14A H 0.193473 0.282501 0.690907 0.024 Uiso 1 1 calc R . . . .
H14B H 0.120446 0.322858 0.558938 0.024 Uiso 1 1 calc R . . . .
C11 C 0.6196(2) 0.46006(15) 0.9267(2) 0.0220(5) Uani 1 1 d . . . . .
H11 H 0.655310 0.411928 0.971478 0.026 Uiso 1 1 calc R . . . .
C13 C 0.4156(2) 0.37589(13) 0.7862(2) 0.0187(4) Uani 1 1 d . . . . .
H13A H 0.485435 0.331058 0.802943 0.022 Uiso 1 1 calc R . . . .
H13B H 0.356995 0.367586 0.838672 0.022 Uiso 1 1 calc R . . . .
C9 C 0.6375(2) 0.60688(15) 0.8997(2) 0.0259(5) Uani 1 1 d . . . . .
H9 H 0.684676 0.657081 0.925740 0.031 Uiso 1 1 calc R . . . .
C4 C -0.0615(3) 0.50285(16) 0.7921(2) 0.0259(5) Uani 1 1 d . . . . .
H4 H -0.114576 0.539438 0.822695 0.031 Uiso 1 1 calc R . . . .
C10 C 0.6904(2) 0.53477(16) 0.9654(2) 0.0248(5) Uani 1 1 d . . . . .
H10 H 0.773599 0.536501 1.035725 0.030 Uiso 1 1 calc R . . . .
C15 C 0.3900(3) 0.32567(13) 0.5709(2) 0.0204(5) Uani 1 1 d . . . . .
C3 C -0.0727(2) 0.41853(16) 0.8074(2) 0.0268(5) Uani 1 1 d . . . . .
H3 H -0.133179 0.398347 0.848297 0.032 Uiso 1 1 calc R . . . .
C17 C 0.2911(3) 0.32990(17) 0.4337(2) 0.0326(6) Uani 1 1 d . . . . .
H17A H 0.203033 0.300199 0.423349 0.049 Uiso 1 1 calc GR . . . .
H17B H 0.339644 0.305366 0.382061 0.049 Uiso 1 1 calc GR . . . .
H17C H 0.268915 0.386761 0.409996 0.049 Uiso 1 1 calc GR . . . .
C18 C 0.5327(3) 0.36824(15) 0.5835(3) 0.0299(5) Uani 1 1 d . . . . .
H18A H 0.514814 0.425212 0.558672 0.045 Uiso 1 1 calc GR . . . .
H18B H 0.577239 0.340844 0.531066 0.045 Uiso 1 1 calc GR . . . .
H18C H 0.596119 0.365481 0.668649 0.045 Uiso 1 1 calc GR . . . .
C16 C 0.4183(3) 0.23427(14) 0.6083(2) 0.0289(5) Uani 1 1 d . . . . .
H16A H 0.484124 0.230660 0.692531 0.043 Uiso 1 1 calc GR . . . .
H16B H 0.459837 0.207182 0.553522 0.043 Uiso 1 1 calc GR . . . .
H16C H 0.328605 0.207759 0.602297 0.043 Uiso 1 1 calc GR . . . .


_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
Sb1 Br1 2.7137(3) . ?
Sb1 N1 2.4458(17) . ?
Sb1 C6 2.153(2) . ?
Sb1 C7 2.151(2) . ?
N1 C14 1.494(3) . ?
N1 C13 1.499(3) . ?
N1 C15 1.524(3) . ?
C6 C1 1.392(3) . ?
C6 C5 1.392(3) . ?
C1 C2 1.393(3) . ?
C1 C14 1.509(3) . ?
C8 C7 1.392(3) . ?
C8 C9 1.386(3) . ?
C5 C4 1.386(4) . ?
C7 C12 1.398(3) . ?
C12 C11 1.392(3) . ?
C12 C13 1.501(3) . ?
C2 C3 1.385(3) . ?
C11 C10 1.386(3) . ?
C9 C10 1.386(4) . ?
C4 C3 1.380(4) . ?
C15 C17 1.537(3) . ?
C15 C18 1.523(3) . ?
C15 C16 1.533(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
N1 Sb1 Br1 162.99(4) . . ?
C6 Sb1 Br1 93.11(6) . . ?
C6 Sb1 N1 75.43(7) . . ?
C7 Sb1 Br1 91.63(6) . . ?
C7 Sb1 N1 77.44(7) . . ?
C7 Sb1 C6 96.17(8) . . ?
C14 N1 Sb1 102.46(12) . . ?
C14 N1 C13 109.11(17) . . ?
C14 N1 C15 112.50(16) . . ?
C13 N1 Sb1 105.27(12) . . ?
C13 N1 C15 112.67(17) . . ?
C15 N1 Sb1 114.11(12) . . ?
C1 C6 Sb1 115.31(16) . . ?
C1 C6 C5 119.5(2) . . ?
C5 C6 Sb1 125.24(17) . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 C14 119.8(2) . . ?
C2 C1 C14 120.4(2) . . ?
C9 C8 C7 120.9(2) . . ?
C4 C5 C6 120.4(2) . . ?
C8 C7 Sb1 124.50(16) . . ?
C8 C7 C12 119.4(2) . . ?
C12 C7 Sb1 116.08(16) . . ?
C7 C12 C13 121.0(2) . . ?
C11 C12 C7 119.5(2) . . ?
C11 C12 C13 119.4(2) . . ?
C3 C2 C1 120.3(2) . . ?
N1 C14 C1 109.75(17) . . ?
C10 C11 C12 120.5(2) . . ?
N1 C13 C12 113.80(18) . . ?
C10 C9 C8 119.6(2) . . ?
C3 C4 C5 120.1(2) . . ?
C9 C10 C11 120.1(2) . . ?
N1 C15 C17 109.80(18) . . ?
N1 C15 C16 111.86(18) . . ?
C18 C15 N1 108.59(17) . . ?
C18 C15 C17 108.5(2) . . ?
C18 C15 C16 109.5(2) . . ?
C16 C15 C17 108.5(2) . . ?
C4 C3 C2 120.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1864561'
loop_
_audit_author_name
_audit_author_address
'Jian Lei, Yongping Liu,  Yi Chen, Chak-Tong Au?  Shuang-Feng Yin'
;Hunan university
China
;
_audit_update_record             
;
2018-08-29 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-08-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 F N Sb'
_chemical_formula_sum            'C18 H21 F N Sb'
_chemical_formula_weight         392.11
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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                   17.7432(9)
_cell_length_b                   10.6409(6)
_cell_length_c                   17.8551(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.996(2)
_cell_angle_gamma                90
_cell_volume                     3346.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3593
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.652
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6539
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1510 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.8769.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         2.236
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.987
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                8161
_reflns_number_total             8232
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.279
_refine_diff_density_min         -2.666
_refine_diff_density_rms         0.556
_refine_ls_abs_structure_details 
;
 Flack x determined using 3988 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(5)
_refine_ls_extinction_coef       0.0123(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         8232
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0869P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C7B(H7BA,H7BB), C8B(H8BA,H8BB), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C11B(H11B), C4(H4), C4B(H4B), C5B(H5B), C3B(H3B), C2B(H2B), C14B(H14B),
 C3(H3), C14(H14), C2(H2), C13B(H13B), C13(H13), C5(H5), C12B(H12B), C11(H11),
 C12(H12)
2.c Idealised Me refined as rotating group:
 C18(H18D,H18E,H18F), C18B(H18A,H18B,H18C), C17(H17D,H17E,H17F), C17B(H17A,
 H17B,H17C), C16(H16D,H16E,H16F), C16B(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Sb1B Sb 0.42814(2) 0.92918(3) 0.66100(2) 0.01894(15) Uani 1 1 d . . . . .
Sb1 Sb 0.53628(2) 0.52771(4) 0.38331(2) 0.02568(16) Uani 1 1 d . . . . .
N1B N 0.4978(3) 1.1295(5) 0.6412(3) 0.0180(9) Uani 1 1 d . . . . .
F1B F 0.3373(2) 0.8133(4) 0.6476(2) 0.0298(8) Uani 1 1 d . . . . .
N1 N 0.6441(3) 0.6048(5) 0.4745(3) 0.0198(9) Uani 1 1 d . . . . .
C7 C 0.6782(4) 0.4904(6) 0.5118(4) 0.0217(11) Uani 1 1 d . . . . .
H7A H 0.656087 0.476870 0.558195 0.026 Uiso 1 1 calc R . . . .
H7B H 0.732157 0.504339 0.525048 0.026 Uiso 1 1 calc R . . . .
C10B C 0.3550(4) 1.0780(6) 0.6885(3) 0.0218(12) Uani 1 1 d . . . . .
C15B C 0.5834(4) 1.1189(6) 0.6506(4) 0.0223(11) Uani 1 1 d . . . . .
C7B C 0.4662(4) 1.1697(6) 0.5642(4) 0.0231(11) Uani 1 1 d . . . . .
H7BA H 0.503143 1.222190 0.543301 0.028 Uiso 1 1 calc R . . . .
H7BB H 0.421120 1.220036 0.567431 0.028 Uiso 1 1 calc R . . . .
C1 C 0.6671(4) 0.3734(6) 0.4641(4) 0.0233(11) Uani 1 1 d . . . . .
C18 C 0.7391(4) 0.6022(9) 0.3833(5) 0.0365(16) Uani 1 1 d . . . . .
H18D H 0.746310 0.518657 0.403221 0.055 Uiso 1 1 calc GR . . . .
H18E H 0.787435 0.637508 0.375848 0.055 Uiso 1 1 calc GR . . . .
H18F H 0.707154 0.599104 0.335882 0.055 Uiso 1 1 calc GR . . . .
C1B C 0.4460(4) 1.0609(6) 0.5119(4) 0.0218(11) Uani 1 1 d . . . . .
C9B C 0.3868(4) 1.1975(6) 0.7024(3) 0.0232(11) Uani 1 1 d . . . . .
F1 F 0.4494(3) 0.4121(6) 0.3447(3) 0.0441(12) Uani 1 1 d . . . . .
C6 C 0.6056(4) 0.3660(7) 0.4067(4) 0.0253(12) Uani 1 1 d . . . . .
C9 C 0.5353(4) 0.6092(6) 0.5466(4) 0.0242(12) Uani 1 1 d . . . . .
C11B C 0.2801(4) 1.0560(8) 0.7006(4) 0.0281(13) Uani 1 1 d . . . . .
H11B H 0.259070 0.976348 0.692521 0.034 Uiso 1 1 calc R . . . .
C6B C 0.4226(3) 0.9468(6) 0.5415(4) 0.0203(11) Uani 1 1 d . . . . .
C4 C 0.6453(5) 0.1546(7) 0.3805(5) 0.0348(16) Uani 1 1 d . . . . .
H4 H 0.638067 0.080950 0.352585 0.042 Uiso 1 1 calc R . . . .
C4B C 0.4084(5) 0.8578(9) 0.4160(4) 0.0337(15) Uani 1 1 d . . . . .
H4B H 0.395984 0.790028 0.383932 0.040 Uiso 1 1 calc R . . . .
C8B C 0.4704(4) 1.2174(6) 0.6964(3) 0.0232(11) Uani 1 1 d . . . . .
H8BA H 0.478503 1.303227 0.680906 0.028 Uiso 1 1 calc R . . . .
H8BB H 0.499343 1.204681 0.745526 0.028 Uiso 1 1 calc R . . . .
C18B C 0.6217(4) 1.2498(7) 0.6549(4) 0.0320(14) Uani 1 1 d . . . . .
H18A H 0.599160 1.300976 0.613928 0.048 Uiso 1 1 calc GR . . . .
H18B H 0.674991 1.240368 0.651567 0.048 Uiso 1 1 calc GR . . . .
H18C H 0.614717 1.289150 0.701971 0.048 Uiso 1 1 calc GR . . . .
C5B C 0.4048(4) 0.8449(7) 0.4939(4) 0.0250(12) Uani 1 1 d . . . . .
H5B H 0.390582 0.768627 0.513507 0.030 Uiso 1 1 calc R . . . .
C17 C 0.6615(5) 0.7928(8) 0.3940(5) 0.0394(18) Uani 1 1 d . . . . .
H17D H 0.616046 0.762656 0.364983 0.059 Uiso 1 1 calc GR . . . .
H17E H 0.694659 0.827810 0.360760 0.059 Uiso 1 1 calc GR . . . .
H17F H 0.648789 0.856361 0.428504 0.059 Uiso 1 1 calc GR . . . .
C8 C 0.6049(4) 0.6777(6) 0.5298(4) 0.0248(12) Uani 1 1 d . . . . .
H8A H 0.590858 0.759901 0.509128 0.030 Uiso 1 1 calc R . . . .
H8B H 0.638955 0.689376 0.575983 0.030 Uiso 1 1 calc R . . . .
C3B C 0.4302(5) 0.9703(10) 0.3868(4) 0.0339(18) Uani 1 1 d . . . . .
H3B H 0.432909 0.978089 0.335345 0.041 Uiso 1 1 calc R . . . .
C10 C 0.4928(4) 0.5410(7) 0.4894(4) 0.0251(13) Uani 1 1 d . . . . .
C2B C 0.4483(4) 1.0719(7) 0.4346(4) 0.0276(14) Uani 1 1 d . . . . .
H2B H 0.462002 1.148117 0.414604 0.033 Uiso 1 1 calc R . . . .
C17B C 0.6105(4) 1.0479(8) 0.7232(4) 0.0262(13) Uani 1 1 d . . . . .
H17A H 0.586350 1.081920 0.763989 0.039 Uiso 1 1 calc GR . . . .
H17B H 0.664561 1.056424 0.734378 0.039 Uiso 1 1 calc GR . . . .
H17C H 0.597643 0.960572 0.716830 0.039 Uiso 1 1 calc GR . . . .
C16 C 0.7625(5) 0.7375(8) 0.4993(5) 0.0359(16) Uani 1 1 d . . . . .
H16D H 0.738206 0.787980 0.534008 0.054 Uiso 1 1 calc GR . . . .
H16E H 0.797458 0.788334 0.475657 0.054 Uiso 1 1 calc GR . . . .
H16F H 0.789400 0.669773 0.526191 0.054 Uiso 1 1 calc GR . . . .
C14B C 0.3442(5) 1.2963(7) 0.7252(4) 0.0323(15) Uani 1 1 d . . . . .
H14B H 0.365505 1.375774 0.732886 0.039 Uiso 1 1 calc R . . . .
C3 C 0.7053(5) 0.1638(7) 0.4371(5) 0.0339(15) Uani 1 1 d . . . . .
H3 H 0.738866 0.097036 0.446841 0.041 Uiso 1 1 calc R . . . .
C14 C 0.5095(5) 0.6175(7) 0.6169(4) 0.0304(14) Uani 1 1 d . . . . .
H14 H 0.538840 0.660005 0.655555 0.036 Uiso 1 1 calc R . . . .
C2 C 0.7153(4) 0.2726(6) 0.4794(4) 0.0285(13) Uani 1 1 d . . . . .
H2 H 0.754949 0.277876 0.518449 0.034 Uiso 1 1 calc R . . . .
C13B C 0.2679(5) 1.2747(9) 0.7366(4) 0.0389(18) Uani 1 1 d . . . . .
H13B H 0.238643 1.340355 0.751769 0.047 Uiso 1 1 calc R . . . .
C15 C 0.7018(4) 0.6834(7) 0.4385(4) 0.0262(13) Uani 1 1 d . . . . .
C13 C 0.4409(5) 0.5641(7) 0.6312(6) 0.0363(17) Uani 1 1 d . . . . .
H13 H 0.424552 0.570419 0.678570 0.044 Uiso 1 1 calc R . . . .
C5 C 0.5953(5) 0.2557(7) 0.3649(4) 0.0315(14) Uani 1 1 d . . . . .
H5 H 0.555038 0.249072 0.326559 0.038 Uiso 1 1 calc R . . . .
C12B C 0.2363(4) 1.1548(9) 0.7251(4) 0.0359(16) Uani 1 1 d . . . . .
H12B H 0.186339 1.140383 0.733674 0.043 Uiso 1 1 calc R . . . .
C11 C 0.4235(4) 0.4893(7) 0.5031(5) 0.0302(14) Uani 1 1 d . . . . .
H11 H 0.394223 0.446072 0.464700 0.036 Uiso 1 1 calc R . . . .
C16B C 0.6092(4) 1.0460(9) 0.5847(5) 0.0332(15) Uani 1 1 d . . . . .
H16A H 0.585578 0.964648 0.581614 0.050 Uiso 1 1 calc GR . . . .
H16B H 0.663343 1.036306 0.592370 0.050 Uiso 1 1 calc GR . . . .
H16C H 0.594762 1.091122 0.538616 0.050 Uiso 1 1 calc GR . . . .
C12 C 0.3976(5) 0.5014(8) 0.5729(6) 0.0359(16) Uani 1 1 d . . . . .
H12 H 0.350942 0.467288 0.580677 0.043 Uiso 1 1 calc R . . . .


_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
Sb1B N1B 2.510(5) . ?
Sb1B F1B 2.020(4) . ?
Sb1B C10B 2.142(6) . ?
Sb1B C6B 2.133(6) . ?
Sb1 N1 2.495(5) . ?
Sb1 F1 2.026(5) . ?
Sb1 C6 2.127(7) . ?
Sb1 C10 2.135(8) . ?
N1B C15B 1.511(8) . ?
N1B C7B 1.484(8) . ?
N1B C8B 1.483(8) . ?
N1 C7 1.480(8) . ?
N1 C8 1.492(8) . ?
N1 C15 1.523(8) . ?
C7 C1 1.507(9) . ?
C10B C9B 1.401(9) . ?
C10B C11B 1.393(10) . ?
C15B C18B 1.547(9) . ?
C15B C17B 1.526(10) . ?
C15B C16B 1.526(10) . ?
C7B C1B 1.504(9) . ?
C1 C6 1.404(9) . ?
C1 C2 1.379(10) . ?
C18 C15 1.523(11) . ?
C1B C6B 1.406(9) . ?
C1B C2B 1.391(9) . ?
C9B C8B 1.515(9) . ?
C9B C14B 1.385(9) . ?
C6 C5 1.391(9) . ?
C9 C8 1.494(9) . ?
C9 C10 1.396(10) . ?
C9 C14 1.391(9) . ?
C11B C12B 1.409(11) . ?
C6B C5B 1.390(9) . ?
C4 C3 1.379(13) . ?
C4 C5 1.401(13) . ?
C4B C5B 1.408(9) . ?
C4B C3B 1.380(13) . ?
C17 C15 1.536(11) . ?
C3B C2B 1.390(12) . ?
C10 C11 1.396(9) . ?
C16 C15 1.544(10) . ?
C14B C13B 1.411(12) . ?
C3 C2 1.381(10) . ?
C14 C13 1.395(12) . ?
C13B C12B 1.399(14) . ?
C13 C12 1.387(14) . ?
C11 C12 1.386(11) . ?

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
F1B Sb1B N1B 154.30(18) . . ?
F1B Sb1B C10B 89.0(2) . . ?
F1B Sb1B C6B 89.8(2) . . ?
C10B Sb1B N1B 74.1(2) . . ?
C6B Sb1B N1B 75.4(2) . . ?
C6B Sb1B C10B 102.0(2) . . ?
F1 Sb1 N1 155.9(2) . . ?
F1 Sb1 C6 88.5(3) . . ?
F1 Sb1 C10 90.0(3) . . ?
C6 Sb1 N1 76.0(2) . . ?
C6 Sb1 C10 98.1(3) . . ?
C10 Sb1 N1 74.3(2) . . ?
C15B N1B Sb1B 115.3(4) . . ?
C7B N1B Sb1B 103.8(4) . . ?
C7B N1B C15B 112.7(5) . . ?
C8B N1B Sb1B 103.6(4) . . ?
C8B N1B C15B 112.3(5) . . ?
C8B N1B C7B 108.4(5) . . ?
C7 N1 Sb1 105.1(4) . . ?
C7 N1 C8 109.2(5) . . ?
C7 N1 C15 112.5(5) . . ?
C8 N1 Sb1 102.7(4) . . ?
C8 N1 C15 112.7(5) . . ?
C15 N1 Sb1 114.0(4) . . ?
N1 C7 C1 114.1(5) . . ?
C9B C10B Sb1B 118.0(5) . . ?
C11B C10B Sb1B 121.8(5) . . ?
C11B C10B C9B 119.8(6) . . ?
N1B C15B C18B 111.6(5) . . ?
N1B C15B C17B 109.9(5) . . ?
N1B C15B C16B 110.1(5) . . ?
C17B C15B C18B 108.2(5) . . ?
C17B C15B C16B 108.0(6) . . ?
C16B C15B C18B 108.9(6) . . ?
N1B C7B C1B 112.8(5) . . ?
C6 C1 C7 119.6(6) . . ?
C2 C1 C7 119.7(6) . . ?
C2 C1 C6 120.6(6) . . ?
C6B C1B C7B 119.4(6) . . ?
C2B C1B C7B 121.2(6) . . ?
C2B C1B C6B 119.4(6) . . ?
C10B C9B C8B 119.4(6) . . ?
C14B C9B C10B 121.3(7) . . ?
C14B C9B C8B 119.3(7) . . ?
C1 C6 Sb1 118.5(5) . . ?
C5 C6 Sb1 122.8(6) . . ?
C5 C6 C1 118.6(7) . . ?
C10 C9 C8 119.5(6) . . ?
C14 C9 C8 121.4(6) . . ?
C14 C9 C10 119.0(7) . . ?
C10B C11B C12B 119.7(8) . . ?
C1B C6B Sb1B 118.2(5) . . ?
C5B C6B Sb1B 121.4(5) . . ?
C5B C6B C1B 120.0(6) . . ?
C3 C4 C5 120.3(7) . . ?
C3B C4B C5B 120.4(7) . . ?
N1B C8B C9B 111.2(5) . . ?
C6B C5B C4B 119.5(7) . . ?
N1 C8 C9 110.1(5) . . ?
C4B C3B C2B 119.9(6) . . ?
C9 C10 Sb1 117.5(5) . . ?
C11 C10 Sb1 123.4(6) . . ?
C11 C10 C9 119.1(7) . . ?
C3B C2B C1B 120.7(7) . . ?
C9B C14B C13B 119.1(8) . . ?
C4 C3 C2 119.8(8) . . ?
C9 C14 C13 122.0(8) . . ?
C1 C2 C3 120.6(7) . . ?
C12B C13B C14B 120.1(7) . . ?
N1 C15 C18 109.2(6) . . ?
N1 C15 C17 109.9(5) . . ?
N1 C15 C16 110.8(6) . . ?
C18 C15 C17 107.8(7) . . ?
C18 C15 C16 110.3(6) . . ?
C17 C15 C16 108.7(6) . . ?
C12 C13 C14 118.3(8) . . ?
C6 C5 C4 120.1(7) . . ?
C13B C12B C11B 120.0(7) . . ?
C12 C11 C10 121.1(8) . . ?
C11 C12 C13 120.4(7) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.294 0.409 0.273 42.5 20.7 ?
2 0.294 0.591 0.773 42.5 20.6 ?
3 0.794 0.091 0.773 42.5 20.6 ?
4 0.794 0.909 0.273 42.5 20.7 ?


_olex2_submission_special_instructions 'No special instructions were received'
