# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_AW010_0ma
_database_code_depnum_ccdc_archive 'CCDC 1500269'
_audit_update_record             
;
2016-08-20 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;
_audit_creation_date             2016-08-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H8 F2 O S'
_chemical_formula_sum            'C12 H8 F2 O S'
_chemical_formula_weight         238.26
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   6.924(5)
_cell_length_b                   8.665(6)
_cell_length_c                   8.772(7)
_cell_angle_alpha                108.778(18)
_cell_angle_beta                 94.634(17)
_cell_angle_gamma                90.550(16)
_cell_volume                     496.3(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1031
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18.16
_cell_measurement_theta_min      2.46
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1035 before and 0.0883 after correction.
The Ratio of minimum to maximum transmission is 0.8199.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5941
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             244.4025
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.2129
_diffrn_reflns_av_unetI/netI     0.1846
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19328
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.46
_diffrn_ambient_temperature      149.98
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                903
_reflns_number_total             1426
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.2148
_refine_diff_density_min         -0.7871
_refine_diff_density_rms         0.2070
_refine_ls_d_res_high            0.9003
_refine_ls_d_res_low             8.2728
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.1245
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.1174
_refine_ls_restrained_S_all      1.1245
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1098P)²+5.6200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2783
_refine_ls_wR_factor_ref         0.3149
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
;
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_refinement_flags_posn
S1 S 0.2445(5) 0.2064(3) 0.2746(3) 0.0382(11) Uani 1.000000 .
O1 O 0.2380(16) 0.2892(11) 0.1609(11) 0.076(3) Uani 1.000000 .
F1 F 0.4805(11) 0.1843(9) 0.2632(8) 0.067(2) Uani 1.000000 .
F2 F 0.0036(11) 0.2269(9) 0.2869(9) 0.069(2) Uani 1.000000 .
C1 C 0.2132(15) -0.0029(12) 0.2483(12) 0.033(3) Uani 1.000000 .
C2 C 0.1720(16) -0.1274(13) 0.1078(13) 0.040(3) Uani 1.000000 .
H2 H 0.1587(16) -0.1097(13) 0.0061(13) 0.048(4) Uiso 1.000000 R
C3 C 0.1501(16) -0.2841(13) 0.1212(16) 0.044(3) Uani 1.000000 .
H3 H 0.1224(16) -0.3753(13) 0.0263(16) 0.053(4) Uiso 1.000000 R
C4 C 0.1681(16) -0.3074(13) 0.2683(15) 0.043(3) Uani 1.000000 .
H4 H 0.1515(16) -0.4143(13) 0.2740(15) 0.052(4) Uiso 1.000000 R
C5 C 0.2104(15) -0.1770(13) 0.4103(14) 0.040(3) Uani 1.000000 .
H5 H 0.2228(15) -0.1941(13) 0.5123(14) 0.048(4) Uiso 1.000000 R
C6 C 0.2340(15) -0.0218(12) 0.3997(12) 0.033(3) Uani 1.000000 .
C7 C 0.2743(16) 0.1338(13) 0.5359(13) 0.038(3) Uani 1.000000 .
C8 C 0.3050(16) 0.1583(15) 0.7000(14) 0.045(3) Uani 1.000000 .
H8 H 0.3030(16) 0.0687(15) 0.7400(14) 0.054(4) Uiso 1.000000 R
C9 C 0.3394(17) 0.3201(18) 0.8071(14) 0.056(4) Uani 1.000000 .
H9 H 0.3604(17) 0.3377(18) 0.9199(14) 0.068(5) Uiso 1.000000 R
C10 C 0.3434(18) 0.4518(16) 0.7529(16) 0.058(4) Uani 1.000000 .
H10 H 0.3649(18) 0.5586(16) 0.8281(16) 0.069(5) Uiso 1.000000 R
C11 C 0.3161(17) 0.4294(14) 0.5873(14) 0.045(3) Uani 1.000000 .
H11 H 0.3199(17) 0.5189(14) 0.5471(14) 0.054(4) Uiso 1.000000 R
C12 C 0.2835(15) 0.2721(12) 0.4855(12) 0.033(3) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.402(9) . ?
S1 F1 1.654(8) . ?
S1 F2 1.688(8) . ?
S1 C1 1.762(10) . ?
S1 C12 1.749(10) . ?
C1 C2 1.358(14) . ?
C1 C6 1.385(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.408(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.364(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(15) . ?
C6 C7 1.492(14) . ?
C7 C8 1.384(15) . ?
C7 C12 1.407(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.420(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.371(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.373(14) . ?

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 S1 O1 90.7(5) . . ?
F2 S1 O1 89.9(5) . . ?
F2 S1 F1 179.3(4) . . ?
C1 S1 O1 130.6(5) . . ?
C1 S1 F1 90.0(4) . . ?
C1 S1 F2 89.4(4) . . ?
C12 S1 O1 132.8(5) . . ?
C12 S1 F1 89.4(4) . . ?
C12 S1 F2 90.4(4) . . ?
C12 S1 C1 96.6(5) . . ?
C2 C1 S1 127.8(9) . . ?
C6 C1 S1 107.9(7) . . ?
C6 C1 C2 124.3(10) . . ?
H2 C2 C1 121.9(7) . . ?
C3 C2 C1 116.3(10) . . ?
C3 C2 H2 121.9(7) . . ?
H3 C3 C2 119.4(7) . . ?
C4 C3 C2 121.1(10) . . ?
C4 C3 H3 119.4(6) . . ?
H4 C4 C3 119.4(6) . . ?
C5 C4 C3 121.2(10) . . ?
C5 C4 H4 119.4(7) . . ?
H5 C5 C4 120.7(7) . . ?
C6 C5 C4 118.6(10) . . ?
C6 C5 H5 120.7(7) . . ?
C5 C6 C1 118.6(10) . . ?
C7 C6 C1 114.2(9) . . ?
C7 C6 C5 127.2(10) . . ?
C8 C7 C6 129.1(11) . . ?
C12 C7 C6 113.5(9) . . ?
C12 C7 C8 117.4(10) . . ?
H8 C8 C7 120.7(7) . . ?
C9 C8 C7 118.6(11) . . ?
C9 C8 H8 120.7(8) . . ?
H9 C9 C8 119.0(8) . . ?
C10 C9 C8 122.1(11) . . ?
C10 C9 H9 119.0(7) . . ?
H10 C10 C9 119.9(7) . . ?
C11 C10 C9 120.3(11) . . ?
C11 C10 H10 119.9(7) . . ?
H11 C11 C10 121.6(7) . . ?
C12 C11 C10 116.9(11) . . ?
C12 C11 H11 121.6(7) . . ?
C7 C12 S1 107.8(7) . . ?
C11 C12 S1 127.3(9) . . ?
C11 C12 C7 124.8(10) . . ?

_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_JHU002_a
_database_code_depnum_ccdc_archive 'CCDC 1500270'
_audit_update_record             
;
2016-08-20 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H12 B F21 O S'
_chemical_formula_weight         914.34

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.6347(17)
_cell_length_b                   9.7850(12)
_cell_length_c                   23.547(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3371.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13168
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.247
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex II CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13441
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.254
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6310
_reflns_number_gt                5099
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.57(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6310
_refine_ls_number_parameters     552
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.53292(9) 0.00554(13) 0.64855(6) 0.0336(3) Uani 1 1 d . . . . .
F1 F 0.37338(18) 0.4848(3) 0.54428(11) 0.0271(6) Uani 1 1 d . . . . .
F20 F 0.4901(2) 0.2047(3) 0.32800(11) 0.0290(6) Uani 1 1 d . . . . .
F16 F 0.3930(2) 0.2024(3) 0.52031(12) 0.0290(6) Uani 1 1 d . . . . .
F10 F 0.64376(19) 0.2591(3) 0.39222(13) 0.0297(6) Uani 1 1 d . . . . .
F15 F 0.59244(19) 0.1627(2) 0.49779(12) 0.0289(6) Uani 1 1 d . . . . .
F6 F 0.4611(2) 0.6581(3) 0.37834(13) 0.0321(7) Uani 1 1 d . . . . .
F5 F 0.3553(2) 0.4276(3) 0.34445(11) 0.0282(6) Uani 1 1 d . . . . .
F11 F 0.5136(2) 0.6332(2) 0.49975(12) 0.0299(6) Uani 1 1 d . . . . .
F14 F 0.7087(2) 0.2056(3) 0.58184(13) 0.0357(7) Uani 1 1 d . . . . .
F2 F 0.2075(2) 0.5896(3) 0.54379(13) 0.0360(7) Uani 1 1 d . . . . .
F7 F 0.5743(2) 0.7567(3) 0.30181(14) 0.0370(7) Uani 1 1 d . . . . .
F19 F 0.4199(2) -0.0402(3) 0.31455(13) 0.0381(7) Uani 1 1 d . . . . .
F17 F 0.3225(2) -0.0454(3) 0.50517(14) 0.0393(8) Uani 1 1 d . . . . .
F9 F 0.75580(19) 0.3602(3) 0.31411(13) 0.0386(7) Uani 1 1 d . . . . .
F13 F 0.7297(2) 0.4588(3) 0.62745(13) 0.0413(8) Uani 1 1 d . . . . .
F4 F 0.1894(2) 0.5378(3) 0.34564(13) 0.0388(7) Uani 1 1 d . . . . .
F12 F 0.6261(2) 0.6705(3) 0.58737(14) 0.0407(8) Uani 1 1 d . . . . .
F3 F 0.1120(2) 0.6211(3) 0.44510(15) 0.0445(8) Uani 1 1 d . . . . .
F18 F 0.3289(2) -0.1673(3) 0.40105(16) 0.0424(8) Uani 1 1 d . . . . .
F8 F 0.7220(2) 0.6104(4) 0.26708(15) 0.0477(8) Uani 1 1 d . . . . .
C27 C 0.6223(3) 0.3821(5) 0.3699(2) 0.0238(10) Uani 1 1 d . . . . .
C21 C 0.3322(3) 0.4971(4) 0.4925(2) 0.0217(9) Uani 1 1 d . . . . .
C25 C 0.3220(3) 0.4693(4) 0.3958(2) 0.0215(9) Uani 1 1 d . . . . .
C15 C 0.4022(3) 0.1457(4) 0.46796(19) 0.0222(9) Uani 1 1 d . . . . .
C34 C 0.6593(3) 0.3115(5) 0.5613(2) 0.0261(10) Uani 1 1 d . . . . .
C20 C 0.3762(3) 0.4538(4) 0.4437(2) 0.0190(9) Uani 1 1 d . . . . .
C30 C 0.5906(3) 0.6321(5) 0.3243(2) 0.0264(10) Uani 1 1 d . . . . .
C19 C 0.4513(3) 0.1481(4) 0.3745(2) 0.0229(10) Uani 1 1 d . . . . .
C35 C 0.6699(3) 0.4389(5) 0.5847(2) 0.0283(11) Uani 1 1 d . . . . .
C29 C 0.6659(3) 0.5590(5) 0.3068(2) 0.0301(11) Uani 1 1 d . . . . .
C32 C 0.5435(3) 0.3952(4) 0.49469(19) 0.0216(9) Uani 1 1 d . . . . .
C22 C 0.2458(3) 0.5521(5) 0.4940(2) 0.0255(10) Uani 1 1 d . . . . .
C14 C 0.4472(3) 0.2182(4) 0.4256(2) 0.0215(9) Uani 1 1 d . . . . .
C28 C 0.6814(3) 0.4327(5) 0.3304(2) 0.0279(11) Uani 1 1 d . . . . .
C33 C 0.5975(3) 0.2919(5) 0.5179(2) 0.0231(9) Uani 1 1 d . . . . .
C9 C 0.4589(4) 0.3935(5) 0.6683(2) 0.0309(11) Uani 1 1 d . . . . .
H9A H 0.4124 0.4541 0.6557 0.037 Uiso 1 1 calc R U . . .
C2 C 0.3958(4) -0.0608(5) 0.7177(2) 0.0286(11) Uani 1 1 d . . . . .
H2A H 0.4203 0.0057 0.7428 0.034 Uiso 1 1 calc R U . . .
C37 C 0.5586(3) 0.5220(4) 0.5197(2) 0.0227(9) Uani 1 1 d . . . . .
C7 C 0.5277(3) 0.1738(5) 0.6701(2) 0.0275(11) Uani 1 1 d . . . . .
C16 C 0.3649(3) 0.0172(5) 0.4613(2) 0.0272(11) Uani 1 1 d . . . . .
C10 C 0.5275(4) 0.4419(5) 0.7042(2) 0.0289(11) Uani 1 1 d . . . . .
C1 C 0.4336(3) -0.0830(4) 0.6645(2) 0.0245(10) Uani 1 1 d . . . . .
C8 C 0.4575(3) 0.2574(5) 0.6507(2) 0.0287(10) Uani 1 1 d . . . . .
H8A H 0.4108 0.2235 0.6266 0.034 Uiso 1 1 calc R U . . .
C24 C 0.2356(3) 0.5251(4) 0.3947(2) 0.0262(10) Uani 1 1 d . . . . .
C36 C 0.6181(3) 0.5450(5) 0.5640(2) 0.0277(11) Uani 1 1 d . . . . .
C31 C 0.5322(3) 0.5782(4) 0.3640(2) 0.0242(10) Uani 1 1 d . . . . .
C3 C 0.3208(4) -0.1397(5) 0.7329(2) 0.0343(12) Uani 1 1 d . . . . .
H3A H 0.2930 -0.1273 0.7690 0.041 Uiso 1 1 calc R U . . .
C26 C 0.5430(3) 0.4485(4) 0.38792(18) 0.0203(9) Uani 1 1 d . . . . .
C17 C 0.3694(3) -0.0459(4) 0.4094(2) 0.0276(11) Uani 1 1 d . . . . .
C6 C 0.4000(4) -0.1805(5) 0.6261(2) 0.0330(12) Uani 1 1 d . . . . .
H6A H 0.4275 -0.1945 0.5900 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5950(4) 0.3536(5) 0.7230(2) 0.0339(12) Uani 1 1 d . . . . .
H12A H 0.6412 0.3863 0.7479 0.041 Uiso 1 1 calc R U . . .
C18 C 0.4150(3) 0.0191(5) 0.3663(2) 0.0265(11) Uani 1 1 d . . . . .
C23 C 0.1965(3) 0.5675(5) 0.4448(2) 0.0265(10) Uani 1 1 d . . . . .
C13 C 0.5959(4) 0.2186(5) 0.7060(2) 0.0325(12) Uani 1 1 d . . . . .
H13A H 0.6423 0.1580 0.7187 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3253(4) -0.2548(5) 0.6435(3) 0.0374(13) Uani 1 1 d . . . . .
H5A H 0.2999 -0.3209 0.6185 0.045 Uiso 1 1 calc R U . . .
C4 C 0.2864(4) -0.2360(5) 0.6958(2) 0.0364(13) Uani 1 1 d . . . . .
H4A H 0.2353 -0.2898 0.7067 0.044 Uiso 1 1 calc R U . . .
C11 C 0.5276(4) 0.5891(5) 0.7218(2) 0.0366(13) Uani 1 1 d . . . . .
H11A H 0.5611 0.5991 0.7575 0.055 Uiso 1 1 calc R U . . .
H11B H 0.4646 0.6204 0.7269 0.055 Uiso 1 1 calc R U . . .
H11C H 0.5573 0.6441 0.6923 0.055 Uiso 1 1 calc R U . . .
B1 B 0.4784(4) 0.3793(5) 0.4384(2) 0.0209(10) Uani 1 1 d . . . . .
F22 F 0.5280(3) 0.0116(3) 0.58358(14) 0.0465(9) Uani 1 1 d . . . . .
O1 O 0.6141(3) -0.0601(4) 0.66540(19) 0.0433(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.407(4) . ?
S1 F22 1.533(3) . ?
S1 C7 1.725(5) . ?
S1 C1 1.733(5) . ?
F1 C21 1.364(5) . ?
F20 C19 1.352(6) . ?
F16 C15 1.358(5) . ?
F10 C27 1.350(5) . ?
F15 C33 1.352(5) . ?
F6 C31 1.345(6) . ?
F5 C25 1.366(5) . ?
F11 C37 1.355(5) . ?
F14 C34 1.354(6) . ?
F2 C22 1.351(5) . ?
F7 C30 1.351(5) . ?
F19 C18 1.352(5) . ?
F17 C16 1.352(6) . ?
F9 C28 1.356(6) . ?
F13 C35 1.348(6) . ?
F4 C24 1.346(6) . ?
F12 C36 1.351(6) . ?
F3 C23 1.343(5) . ?
F18 C17 1.342(5) . ?
F8 C29 1.343(6) . ?
C27 C28 1.362(7) . ?
C27 C26 1.397(7) . ?
C21 C22 1.375(7) . ?
C21 C20 1.385(7) . ?
C25 C24 1.378(7) . ?
C25 C20 1.386(7) . ?
C15 C16 1.380(7) . ?
C15 C14 1.391(7) . ?
C34 C35 1.373(7) . ?
C34 C33 1.377(7) . ?
C20 B1 1.668(7) . ?
C30 C31 1.371(7) . ?
C30 C29 1.377(8) . ?
C19 C18 1.383(7) . ?
C19 C14 1.385(7) . ?
C35 C36 1.375(7) . ?
C29 C28 1.374(7) . ?
C32 C37 1.392(6) . ?
C32 C33 1.395(6) . ?
C32 B1 1.640(7) . ?
C22 C23 1.372(7) . ?
C14 B1 1.669(7) . ?
C9 C8 1.395(7) . ?
C9 C10 1.395(7) . ?
C9 H9A 0.9500 . ?
C2 C1 1.388(7) . ?
C2 C3 1.389(7) . ?
C2 H2A 0.9500 . ?
C37 C36 1.378(7) . ?
C7 C13 1.380(8) . ?
C7 C8 1.389(7) . ?
C16 C17 1.371(7) . ?
C10 C12 1.385(7) . ?
C10 C11 1.498(7) . ?
C1 C6 1.402(7) . ?
C8 H8A 0.9500 . ?
C24 C23 1.375(7) . ?
C31 C26 1.397(6) . ?
C3 C4 1.380(7) . ?
C3 H3A 0.9500 . ?
C26 B1 1.663(7) . ?
C17 C18 1.372(7) . ?
C6 C5 1.376(8) . ?
C6 H6A 0.9500 . ?
C12 C13 1.380(7) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C5 C4 1.368(8) . ?
C5 H5A 0.9500 . ?
C4 H4A 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 F22 109.8(2) . . ?
O1 S1 C7 113.0(3) . . ?
F22 S1 C7 104.7(2) . . ?
O1 S1 C1 114.7(2) . . ?
F22 S1 C1 101.3(2) . . ?
C7 S1 C1 112.1(2) . . ?
F10 C27 C28 116.3(4) . . ?
F10 C27 C26 119.3(4) . . ?
C28 C27 C26 124.4(4) . . ?
F1 C21 C22 114.8(4) . . ?
F1 C21 C20 120.7(4) . . ?
C22 C21 C20 124.6(5) . . ?
F5 C25 C24 115.5(4) . . ?
F5 C25 C20 118.9(4) . . ?
C24 C25 C20 125.7(4) . . ?
F16 C15 C16 115.8(4) . . ?
F16 C15 C14 119.3(4) . . ?
C16 C15 C14 124.8(4) . . ?
F14 C34 C35 119.4(4) . . ?
F14 C34 C33 120.7(4) . . ?
C35 C34 C33 119.9(4) . . ?
C21 C20 C25 112.1(4) . . ?
C21 C20 B1 127.7(4) . . ?
C25 C20 B1 120.0(4) . . ?
F7 C30 C31 120.3(4) . . ?
F7 C30 C29 119.5(4) . . ?
C31 C30 C29 120.2(4) . . ?
F20 C19 C18 114.9(4) . . ?
F20 C19 C14 121.2(4) . . ?
C18 C19 C14 123.8(5) . . ?
F13 C35 C34 120.3(4) . . ?
F13 C35 C36 120.9(4) . . ?
C34 C35 C36 118.7(4) . . ?
F8 C29 C28 121.2(5) . . ?
F8 C29 C30 120.3(5) . . ?
C28 C29 C30 118.5(4) . . ?
C37 C32 C33 113.0(4) . . ?
C37 C32 B1 121.2(4) . . ?
C33 C32 B1 125.3(4) . . ?
F2 C22 C23 119.0(4) . . ?
F2 C22 C21 120.6(5) . . ?
C23 C22 C21 120.4(5) . . ?
C19 C14 C15 113.0(4) . . ?
C19 C14 B1 127.8(4) . . ?
C15 C14 B1 118.8(4) . . ?
F9 C28 C27 120.8(5) . . ?
F9 C28 C29 119.3(4) . . ?
C27 C28 C29 119.9(5) . . ?
F15 C33 C34 115.2(4) . . ?
F15 C33 C32 120.6(4) . . ?
C34 C33 C32 124.2(4) . . ?
C8 C9 C10 121.0(5) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C1 C2 C3 117.4(4) . . ?
C1 C2 H2A 121.3 . . ?
C3 C2 H2A 121.3 . . ?
F11 C37 C36 116.0(4) . . ?
F11 C37 C32 119.5(4) . . ?
C36 C37 C32 124.5(4) . . ?
C13 C7 C8 123.3(5) . . ?
C13 C7 S1 116.8(4) . . ?
C8 C7 S1 119.9(4) . . ?
F17 C16 C17 119.9(4) . . ?
F17 C16 C15 120.5(5) . . ?
C17 C16 C15 119.5(5) . . ?
C12 C10 C9 119.6(5) . . ?
C12 C10 C11 120.8(5) . . ?
C9 C10 C11 119.6(5) . . ?
C2 C1 C6 123.3(5) . . ?
C2 C1 S1 116.8(4) . . ?
C6 C1 S1 119.7(4) . . ?
C7 C8 C9 117.0(5) . . ?
C7 C8 H8A 121.5 . . ?
C9 C8 H8A 121.5 . . ?
F4 C24 C23 120.0(4) . . ?
F4 C24 C25 120.9(4) . . ?
C23 C24 C25 119.1(4) . . ?
F12 C36 C35 119.6(4) . . ?
F12 C36 C37 120.7(4) . . ?
C35 C36 C37 119.6(4) . . ?
F6 C31 C30 115.5(4) . . ?
F6 C31 C26 120.9(4) . . ?
C30 C31 C26 123.6(4) . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C27 C26 C31 113.2(4) . . ?
C27 C26 B1 120.0(4) . . ?
C31 C26 B1 126.4(4) . . ?
F18 C17 C16 120.6(5) . . ?
F18 C17 C18 121.1(5) . . ?
C16 C17 C18 118.3(4) . . ?
C5 C6 C1 116.5(5) . . ?
C5 C6 H6A 121.7 . . ?
C1 C6 H6A 121.7 . . ?
C13 C12 C10 120.8(5) . . ?
C13 C12 H12A 119.6 . . ?
C10 C12 H12A 119.6 . . ?
F19 C18 C17 119.6(4) . . ?
F19 C18 C19 119.8(5) . . ?
C17 C18 C19 120.5(4) . . ?
F3 C23 C22 121.5(5) . . ?
F3 C23 C24 120.4(4) . . ?
C22 C23 C24 118.1(4) . . ?
C12 C13 C7 118.3(5) . . ?
C12 C13 H13A 120.8 . . ?
C7 C13 H13A 120.8 . . ?
C4 C5 C6 121.8(5) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C32 B1 C26 102.0(4) . . ?
C32 B1 C20 114.8(4) . . ?
C26 B1 C20 112.7(4) . . ?
C32 B1 C14 113.2(4) . . ?
C26 B1 C14 114.3(4) . . ?
C20 B1 C14 100.4(4) . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.062



####################################################################### 
# 
# 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_JT035_0m
_database_code_depnum_ccdc_archive 'CCDC 1500271'
_audit_update_record             
;
2016-08-20 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;
_audit_creation_date             2016-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C12 H10 F O S, B C24 F20'
_chemical_formula_sum            'C36 H10 B F21 O S'
_chemical_formula_weight         900.34
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   15.0990(3)
_cell_length_b                   18.8792(5)
_cell_length_c                   23.1430(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6597.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6229
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.76
_cell_measurement_theta_min      2.47
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0566 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.9516.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.8128
_exptl_crystal_description       block
_exptl_crystal_F_000             3556.7420
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33498
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.76
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              0
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                5262
_reflns_number_total             7575
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.4524
_refine_diff_density_min         -0.5701
_refine_diff_density_rms         0.0969
_refine_ls_d_res_high            0.7694
_refine_ls_d_res_low             11.5715
_refine_ls_goodness_of_fit_ref   1.0348
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7575
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.0339
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+2.1955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0966
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
O1A \\sim F1B: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(O1A) \\sim Ueq, Uanis(F1B) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(O1A) = Uanis(O1B)
Uanis(F1A) = Uanis(F1B)
3. Same fragment restrains
{O1B, F1B} sigma for 1-2: 0.02, 1-3: 0.04
{O1A, F1A} sigma for 1-2: 0.02, 1-3: 0.04
as
{O1A, F1A}
4. Others
 Sof(O1B)=Sof(F1B)=1-FVAR(1)
 Sof(O1A)=Sof(F1A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C8(H8), C2(H2), C12(H12), C11(H11), C10(H10), C9(H9),
 C3(H3)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
S1 S 0.17425(4) 0.22579(3) 0.39846(3) 0.03284(14) Uani 1.000000 . . .
C6 C 0.17540(14) 0.28886(11) 0.29346(10) 0.0301(5) Uani 1.000000 . . .
H6 H 0.13603(14) 0.25287(11) 0.28068(10) 0.0361(6) Uiso 1.000000 R . .
C7 C 0.25273(13) 0.16039(11) 0.40890(9) 0.0261(5) Uani 1.000000 . . .
C1 C 0.20708(13) 0.28981(10) 0.34973(9) 0.0253(5) Uani 1.000000 . . .
C5 C 0.20307(14) 0.34202(11) 0.25667(10) 0.0305(5) Uani 1.000000 . . .
H5 H 0.18219(14) 0.34328(11) 0.21796(10) 0.0366(6) Uiso 1.000000 R . .
C4 C 0.26070(16) 0.39306(13) 0.27594(10) 0.0385(6) Uani 1.000000 . . .
H4 H 0.27922(16) 0.42949(13) 0.25033(10) 0.0463(7) Uiso 1.000000 R . .
C8 C 0.26722(15) 0.13482(12) 0.46402(10) 0.0354(5) Uani 1.000000 . . .
H8 H 0.23825(15) 0.15500(12) 0.49653(10) 0.0425(7) Uiso 1.000000 R . .
C2 C 0.26581(16) 0.34037(13) 0.36974(11) 0.0410(6) Uani 1.000000 . . .
H2 H 0.28718(16) 0.33922(13) 0.40834(11) 0.0492(7) Uiso 1.000000 R . .
C12 C 0.29657(15) 0.13369(13) 0.36101(10) 0.0380(6) Uani 1.000000 . . .
H12 H 0.28705(15) 0.15335(13) 0.32374(10) 0.0456(7) Uiso 1.000000 R . .
C11 C 0.35435(17) 0.07793(14) 0.36874(12) 0.0472(7) Uani 1.000000 . . .
H11 H 0.38475(17) 0.05848(14) 0.33649(12) 0.0566(8) Uiso 1.000000 R . .
C10 C 0.36803(15) 0.05043(13) 0.42302(11) 0.0417(6) Uani 1.000000 . . .
H10 H 0.40726(15) 0.01154(13) 0.42785(11) 0.0500(8) Uiso 1.000000 R . .
C9 C 0.32592(15) 0.07832(13) 0.47020(12) 0.0427(6) Uani 1.000000 . . .
H9 H 0.33678(15) 0.05903(13) 0.50745(12) 0.0513(8) Uiso 1.000000 R . .
C3 C 0.29217(18) 0.39228(14) 0.33196(11) 0.0527(7) Uani 1.000000 . . .
H3 H 0.33231(18) 0.42789(14) 0.34442(11) 0.0632(9) Uiso 1.000000 R . .
F11 F 0.41534(7) 0.01506(6) 0.59793(5) 0.0270(3) Uani 1.000000 . . .
F12 F 0.23607(7) 0.04662(6) 0.65152(5) 0.0275(3) Uani 1.000000 . . .
F2 F 0.17534(8) -0.06987(6) 0.71801(5) 0.0304(3) Uani 1.000000 . . .
F16 F 0.22241(7) -0.14349(6) 0.51814(5) 0.0278(3) Uani 1.000000 . . .
F13 F 0.12210(8) 0.11806(6) 0.58797(6) 0.0364(3) Uani 1.000000 . . .
F6 F 0.26523(7) -0.25673(6) 0.59368(5) 0.0282(3) Uani 1.000000 . . .
F17 F 0.38197(8) -0.07961(6) 0.50460(5) 0.0296(3) Uani 1.000000 . . .
F14 F 0.06074(8) 0.06412(7) 0.48618(6) 0.0388(3) Uani 1.000000 . . .
F21 F 0.40468(7) -0.21763(6) 0.67525(5) 0.0274(3) Uani 1.000000 . . .
F5 F 0.14204(8) -0.33796(6) 0.63798(6) 0.0352(3) Uani 1.000000 . . .
F20 F 0.53854(8) -0.28867(7) 0.62866(6) 0.0423(3) Uani 1.000000 . . .
F3 F 0.05207(8) -0.15468(7) 0.76233(6) 0.0409(3) Uani 1.000000 . . .
F10 F 0.52860(7) 0.08540(6) 0.66438(6) 0.0341(3) Uani 1.000000 . . .
F7 F 0.33132(8) -0.12446(6) 0.75902(5) 0.0310(3) Uani 1.000000 . . .
F15 F 0.11144(8) -0.06819(7) 0.45304(5) 0.0375(3) Uani 1.000000 . . .
F9 F 0.53843(9) 0.05721(7) 0.78037(6) 0.0447(4) Uani 1.000000 . . .
F18 F 0.51186(8) -0.15343(7) 0.45857(6) 0.0428(3) Uani 1.000000 . . .
F8 F 0.43791(9) -0.04922(7) 0.82519(6) 0.0439(4) Uani 1.000000 . . .
F19 F 0.59349(8) -0.25935(7) 0.51895(6) 0.0459(4) Uani 1.000000 . . .
F4 F 0.03424(8) -0.29022(7) 0.72454(6) 0.0431(4) Uani 1.000000 . . .
C24 C 0.41737(12) -0.00229(10) 0.65473(9) 0.0212(4) Uani 1.000000 . . .
C25 C 0.23962(11) -0.05199(10) 0.58729(8) 0.0189(4) Uani 1.000000 . . .
C31 C 0.38392(11) -0.14530(10) 0.59250(9) 0.0193(4) Uani 1.000000 . . .
C30 C 0.20170(12) -0.07737(10) 0.53657(9) 0.0215(4) Uani 1.000000 . . .
C18 C 0.21556(12) -0.22746(10) 0.63626(9) 0.0205(4) Uani 1.000000 . . .
C19 C 0.36308(12) -0.05654(10) 0.67481(9) 0.0197(4) Uani 1.000000 . . .
C13 C 0.23106(12) -0.15867(10) 0.65541(8) 0.0193(4) Uani 1.000000 . . .
C32 C 0.41708(12) -0.13159(10) 0.53803(9) 0.0225(4) Uani 1.000000 . . .
C36 C 0.42951(12) -0.19910(10) 0.62107(9) 0.0221(4) Uani 1.000000 . . .
C33 C 0.48577(13) -0.16870(11) 0.51289(9) 0.0279(5) Uani 1.000000 . . .
C20 C 0.37507(13) -0.07006(10) 0.73290(9) 0.0227(4) Uani 1.000000 . . .
C28 C 0.11594(12) 0.02598(11) 0.51946(9) 0.0258(5) Uani 1.000000 . . .
C23 C 0.47633(12) 0.03588(10) 0.68826(10) 0.0262(5) Uani 1.000000 . . .
C26 C 0.20811(12) 0.01469(10) 0.60253(9) 0.0214(4) Uani 1.000000 . . .
C34 C 0.52658(13) -0.22215(11) 0.54300(10) 0.0305(5) Uani 1.000000 . . .
C22 C 0.48250(13) 0.02086(11) 0.74637(10) 0.0294(5) Uani 1.000000 . . .
C16 C 0.09626(12) -0.24780(11) 0.70130(10) 0.0281(5) Uani 1.000000 . . .
C35 C 0.49864(13) -0.23722(11) 0.59808(10) 0.0271(5) Uani 1.000000 . . .
C27 C 0.14777(12) 0.05320(10) 0.57020(10) 0.0250(5) Uani 1.000000 . . .
C29 C 0.14269(12) -0.04065(12) 0.50268(9) 0.0260(5) Uani 1.000000 . . .
C14 C 0.17133(12) -0.13712(10) 0.69721(9) 0.0222(4) Uani 1.000000 . . .
C15 C 0.10627(13) -0.17947(11) 0.72059(9) 0.0266(5) Uani 1.000000 . . .
C21 C 0.43144(14) -0.03254(11) 0.76869(9) 0.0286(5) Uani 1.000000 . . .
C17 C 0.15069(13) -0.27171(10) 0.65817(9) 0.0239(5) Uani 1.000000 . . .
B1 B 0.30440(14) -0.10281(11) 0.62746(10) 0.0190(5) Uani 1.000000 . . .
O1A O 0.0866(10) 0.1990(5) 0.3840(4) 0.0369(9) Uani 0.364(13) D U 1
F1A F 0.1715(5) 0.2617(5) 0.4551(5) 0.0327(8) Uani 0.364(13) D . 1
O1B O 0.1488(5) 0.2562(3) 0.4536(3) 0.0369(9) Uani 0.636(13) D . 2
F1B F 0.0975(4) 0.1903(2) 0.37036(18) 0.0327(8) Uani 0.636(13) D U 2


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.728(2) . ?
S1 C1 1.726(2) . ?
S1 O1A 1.455(16) . ?
S1 F1A 1.477(13) . ?
S1 O1B 1.452(9) . ?
S1 F1B 1.489(6) . ?
C6 C1 1.387(3) . ?
C6 C5 1.381(3) . ?
C7 C8 1.381(3) . ?
C7 C12 1.386(3) . ?
C1 C2 1.383(3) . ?
C5 C4 1.373(3) . ?
C4 C3 1.381(3) . ?
C8 C9 1.394(3) . ?
C2 C3 1.372(3) . ?
C12 C11 1.379(3) . ?
C11 C10 1.375(3) . ?
C10 C9 1.369(4) . ?
F11 C24 1.355(2) . ?
F12 C26 1.352(2) . ?
F2 C14 1.359(2) . ?
F16 C30 1.356(2) . ?
F13 C27 1.349(2) . ?
F6 C18 1.356(2) . ?
F17 C32 1.357(2) . ?
F14 C28 1.344(2) . ?
F21 C36 1.355(2) . ?
F5 C17 1.342(2) . ?
F20 C35 1.344(2) . ?
F3 C15 1.350(2) . ?
F10 C23 1.342(2) . ?
F7 C20 1.362(2) . ?
F15 C29 1.346(2) . ?
F9 C22 1.343(2) . ?
F18 C33 1.348(2) . ?
F8 C21 1.348(2) . ?
F19 C34 1.351(2) . ?
F4 C16 1.345(2) . ?
C24 C19 1.392(3) . ?
C24 C23 1.383(3) . ?
C25 C30 1.391(3) . ?
C25 C26 1.391(3) . ?
C25 B1 1.656(3) . ?
C31 C32 1.381(3) . ?
C31 C36 1.394(3) . ?
C31 B1 1.655(3) . ?
C30 C29 1.375(3) . ?
C18 C13 1.392(3) . ?
C18 C17 1.384(3) . ?
C19 C20 1.380(3) . ?
C19 B1 1.658(3) . ?
C13 C14 1.384(3) . ?
C13 B1 1.660(3) . ?
C32 C33 1.380(3) . ?
C36 C35 1.375(3) . ?
C33 C34 1.372(3) . ?
C20 C21 1.383(3) . ?
C28 C27 1.369(3) . ?
C28 C29 1.377(3) . ?
C23 C22 1.378(3) . ?
C26 C27 1.385(3) . ?
C34 C35 1.372(3) . ?
C22 C21 1.370(3) . ?
C16 C15 1.373(3) . ?
C16 C17 1.369(3) . ?
C14 C15 1.377(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
C1 S1 C7 113.25(10) . . ?
F1A S1 O1A 109.7(4) . . ?
F1B S1 O1B 110.8(2) . . ?
C5 C6 C1 117.7(2) . . ?
C8 C7 S1 119.17(17) . . ?
C12 C7 S1 118.39(16) . . ?
C12 C7 C8 122.4(2) . . ?
C6 C1 S1 120.35(16) . . ?
C2 C1 S1 116.67(17) . . ?
C2 C1 C6 123.0(2) . . ?
C4 C5 C6 120.1(2) . . ?
C3 C4 C5 121.0(2) . . ?
C9 C8 C7 117.6(2) . . ?
C3 C2 C1 117.7(2) . . ?
C11 C12 C7 118.4(2) . . ?
C10 C11 C12 120.1(2) . . ?
C9 C10 C11 120.9(2) . . ?
C10 C9 C8 120.5(2) . . ?
C2 C3 C4 120.4(2) . . ?
C19 C24 F11 119.24(17) . . ?
C23 C24 F11 115.64(17) . . ?
C23 C24 C19 125.11(19) . . ?
C26 C25 C30 112.64(17) . . ?
B1 C25 C30 121.14(16) . . ?
B1 C25 C26 125.74(17) . . ?
C36 C31 C32 113.00(17) . . ?
B1 C31 C32 128.20(17) . . ?
B1 C31 C36 118.65(17) . . ?
C25 C30 F16 119.19(17) . . ?
C29 C30 F16 115.74(18) . . ?
C29 C30 C25 125.06(18) . . ?
C13 C18 F6 121.23(16) . . ?
C17 C18 F6 114.32(17) . . ?
C17 C18 C13 124.45(18) . . ?
C20 C19 C24 112.59(17) . . ?
B1 C19 C24 118.80(18) . . ?
B1 C19 C20 128.05(17) . . ?
C14 C13 C18 112.78(17) . . ?
B1 C13 C18 125.50(17) . . ?
B1 C13 C14 121.36(17) . . ?
C31 C32 F17 120.95(17) . . ?
C33 C32 F17 114.84(18) . . ?
C33 C32 C31 124.20(19) . . ?
C31 C36 F21 119.38(17) . . ?
C35 C36 F21 115.66(18) . . ?
C35 C36 C31 124.94(19) . . ?
C32 C33 F18 120.26(19) . . ?
C34 C33 F18 119.96(18) . . ?
C34 C33 C32 119.8(2) . . ?
C19 C20 F7 120.53(17) . . ?
C21 C20 F7 114.76(18) . . ?
C21 C20 C19 124.71(18) . . ?
C27 C28 F14 120.53(19) . . ?
C29 C28 F14 120.65(19) . . ?
C29 C28 C27 118.81(18) . . ?
C24 C23 F10 120.7(2) . . ?
C22 C23 F10 120.36(18) . . ?
C22 C23 C24 118.93(19) . . ?
C25 C26 F12 120.63(17) . . ?
C27 C26 F12 115.11(17) . . ?
C27 C26 C25 124.26(19) . . ?
C33 C34 F19 120.6(2) . . ?
C35 C34 F19 120.3(2) . . ?
C35 C34 C33 119.09(18) . . ?
C23 C22 F9 120.62(19) . . ?
C21 C22 F9 120.6(2) . . ?
C21 C22 C23 118.78(18) . . ?
C15 C16 F4 120.41(19) . . ?
C17 C16 F4 120.88(19) . . ?
C17 C16 C15 118.71(18) . . ?
C36 C35 F20 121.0(2) . . ?
C34 C35 F20 120.07(18) . . ?
C34 C35 C36 118.95(19) . . ?
C28 C27 F13 120.10(18) . . ?
C26 C27 F13 120.06(19) . . ?
C26 C27 C28 119.81(18) . . ?
C30 C29 F15 121.28(19) . . ?
C28 C29 F15 119.38(18) . . ?
C28 C29 C30 119.33(19) . . ?
C13 C14 F2 119.55(17) . . ?
C15 C14 F2 115.77(17) . . ?
C15 C14 C13 124.68(18) . . ?
C16 C15 F3 119.44(18) . . ?
C14 C15 F3 120.83(18) . . ?
C14 C15 C16 119.74(19) . . ?
C20 C21 F8 120.38(19) . . ?
C22 C21 F8 119.78(19) . . ?
C22 C21 C20 119.8(2) . . ?
C18 C17 F5 120.28(18) . . ?
C16 C17 F5 120.18(18) . . ?
C16 C17 C18 119.54(18) . . ?
C31 B1 C25 115.78(16) . . ?
C19 B1 C25 112.42(15) . . ?
C19 B1 C31 101.00(14) . . ?
C13 B1 C25 101.11(14) . . ?
C13 B1 C31 111.50(15) . . ?
C13 B1 C19 115.69(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
O1A 0.2000
F1B 0.2000

####################################################################### 
# 
# 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_AW009_0ma
_database_code_depnum_ccdc_archive 'CCDC 1500272'
_audit_update_record             
;
2016-08-20 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;
_audit_creation_date             2016-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C12 H8 F O S, B0.5 C12 F10'
_chemical_formula_sum            'C24 H8 B0.5 F11 O S'
_chemical_formula_weight         558.79
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   25.433(3)
_cell_length_b                   8.7969(10)
_cell_length_c                   18.856(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.150(5)
_cell_angle_gamma                90
_cell_volume                     4186.0(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2861
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.35
_cell_measurement_theta_min      2.45
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0694 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.8926.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.7732
_exptl_crystal_description       block
_exptl_crystal_F_000             2223.1073
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23038
_diffrn_reflns_theta_full        27.5238
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.61
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9952
_diffrn_measured_fraction_theta_max 0.9952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              32
_reflns_limit_h_min              -32
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2866
_reflns_number_total             4812
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.7964
_refine_diff_density_min         -0.7083
_refine_diff_density_rms         0.1823
_refine_ls_d_res_high            0.7690
_refine_ls_d_res_low             12.6176
_refine_ls_goodness_of_fit_ref   1.0457
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4812
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.0457
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+9.7622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1487
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
S1 S 0.26941(4) 1.05695(12) 0.08488(6) 0.0336(3) Uani 1.000000 1 . . .
O1 O 0.28763(12) 1.1739(3) 0.13373(16) 0.0479(8) Uani 1.000000 1 . . .
F1 F 0.22131(10) 1.1020(3) 0.03701(15) 0.0540(7) Uani 1.000000 1 . . .
F2 F 0.37855(8) 0.8998(2) 0.23055(10) 0.0279(5) Uani 1.000000 1 . . .
F3 F 0.33014(9) 0.6935(3) 0.30056(13) 0.0415(6) Uani 1.000000 1 . . .
F4 F 0.38622(9) 0.5054(3) 0.39671(12) 0.0408(6) Uani 1.000000 1 . . .
F5 F 0.49333(9) 0.5331(2) 0.42300(11) 0.0336(5) Uani 1.000000 1 . . .
F6 F 0.54326(8) 0.7494(2) 0.35820(10) 0.0282(5) Uani 1.000000 1 . . .
F7 F 0.42178(8) 1.1641(2) 0.29341(10) 0.0250(5) Uani 1.000000 1 . . .
F8 F 0.37152(8) 1.3891(2) 0.21770(12) 0.0350(6) Uani 1.000000 1 . . .
F9 F 0.38671(9) 1.4320(3) 0.07868(12) 0.0425(6) Uani 1.000000 1 . . .
F10 F 0.45422(9) 1.2493(2) 0.01819(10) 0.0329(5) Uani 1.000000 1 . . .
F11 F 0.50323(8) 1.0232(2) 0.09036(10) 0.0272(5) Uani 1.000000 1 . . .
B1 B 0.5 0.9563(6) 0.25 0.0164(11) Uani 1.000000 2 S T P
C1 C 0.31627(14) 0.9882(4) 0.03310(19) 0.0232(8) Uani 1.000000 1 . . .
C2 C 0.34445(15) 1.0726(4) -0.0116(2) 0.0282(9) Uani 1.000000 1 . . .
H2 H 0.33959(15) 1.1792(4) -0.0171(2) 0.0339(10) Uiso 1.000000 1 R . .
C3 C 0.37985(15) 0.9944(4) -0.0479(2) 0.0290(9) Uani 1.000000 1 . . .
H3 H 0.40017(15) 1.0478(4) -0.0788(2) 0.0347(10) Uiso 1.000000 1 R . .
C4 C 0.38601(15) 0.8392(4) -0.03962(19) 0.0298(9) Uani 1.000000 1 . . .
H4 H 0.41067(15) 0.7876(4) -0.06497(19) 0.0358(11) Uiso 1.000000 1 R . .
C5 C 0.35707(15) 0.7570(4) 0.00475(19) 0.0279(9) Uani 1.000000 1 . . .
H5 H 0.36166(15) 0.6501(4) 0.00949(19) 0.0335(10) Uiso 1.000000 1 R . .
C6 C 0.32157(13) 0.8317(4) 0.04193(18) 0.0230(8) Uani 1.000000 1 . . .
C7 C 0.28719(14) 0.7693(4) 0.09255(18) 0.0236(8) Uani 1.000000 1 . . .
C8 C 0.28084(15) 0.6201(4) 0.11236(19) 0.0294(9) Uani 1.000000 1 . . .
H8 H 0.30063(15) 0.5416(4) 0.09340(19) 0.0353(11) Uiso 1.000000 1 R . .
C9 C 0.24529(15) 0.5856(5) 0.1602(2) 0.0329(9) Uani 1.000000 1 . . .
H9 H 0.24055(15) 0.4827(5) 0.1733(2) 0.0395(11) Uiso 1.000000 1 R . .
C10 C 0.21668(15) 0.6981(5) 0.1892(2) 0.0358(10) Uani 1.000000 1 . . .
H10 H 0.19276(15) 0.6719(5) 0.2221(2) 0.0430(12) Uiso 1.000000 1 R . .
C11 C 0.22256(15) 0.8490(5) 0.1707(2) 0.0343(10) Uani 1.000000 1 . . .
H11 H 0.20344(15) 0.9275(5) 0.1907(2) 0.0411(12) Uiso 1.000000 1 R . .
C12 C 0.25741(14) 0.8812(4) 0.12170(18) 0.0258(8) Uani 1.000000 1 . . .
C13 C 0.46407(14) 0.8399(4) 0.29192(17) 0.0189(7) Uani 1.000000 1 . . .
C14 C 0.49013(13) 0.7389(4) 0.34177(17) 0.0208(8) Uani 1.000000 1 . . .
C15 C 0.46555(15) 0.6271(4) 0.37599(18) 0.0236(8) Uani 1.000000 1 . . .
C16 C 0.41114(15) 0.6119(4) 0.36246(19) 0.0268(9) Uani 1.000000 1 . . .
C17 C 0.38341(14) 0.7066(4) 0.31379(19) 0.0247(8) Uani 1.000000 1 . . .
C18 C 0.40974(14) 0.8161(4) 0.27945(17) 0.0197(8) Uani 1.000000 1 . . .
C19 C 0.46452(13) 1.0778(4) 0.19609(17) 0.0180(7) Uani 1.000000 1 . . .
C20 C 0.47034(13) 1.1075(4) 0.12523(17) 0.0196(8) Uani 1.000000 1 . . .
C21 C 0.44541(14) 1.2251(4) 0.08631(17) 0.0235(8) Uani 1.000000 1 . . .
C22 C 0.41220(14) 1.3199(4) 0.11653(19) 0.0250(8) Uani 1.000000 1 . . .
C23 C 0.40447(14) 1.2963(4) 0.1870(2) 0.0256(8) Uani 1.000000 1 . . .
C24 C 0.43045(13) 1.1787(4) 0.22401(17) 0.0193(7) Uani 1.000000 1 . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.420(3) . ?
S1 F1 1.481(3) . ?
S1 C1 1.740(3) . ?
S1 C12 1.738(4) . ?
F2 C18 1.356(4) . ?
F3 C17 1.352(4) . ?
F4 C16 1.341(4) . ?
F5 C15 1.346(4) . ?
F6 C14 1.351(4) . ?
F7 C24 1.360(4) . ?
F8 C23 1.351(4) . ?
F9 C22 1.337(4) . ?
F10 C21 1.348(4) . ?
F11 C20 1.349(4) . ?
B1 C13 1.640(5) 2_655 ?
B1 C13 1.640(5) . ?
B1 C19 1.662(5) . ?
B1 C19 1.662(5) 2_655 ?
C1 C2 1.388(5) . ?
C1 C6 1.391(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(5) . ?
C6 C7 1.478(5) . ?
C7 C8 1.380(5) . ?
C7 C12 1.396(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(5) . ?
C13 C14 1.399(5) . ?
C13 C18 1.388(5) . ?
C14 C15 1.369(5) . ?
C15 C16 1.382(5) . ?
C16 C17 1.369(5) . ?
C17 C18 1.380(5) . ?
C19 C20 1.387(4) . ?
C19 C24 1.389(5) . ?
C20 C21 1.377(5) . ?
C21 C22 1.361(5) . ?
C22 C23 1.383(5) . ?
C23 C24 1.370(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
F1 S1 O1 112.33(18) . . ?
C1 S1 O1 115.14(18) . . ?
C1 S1 F1 108.81(16) . . ?
C12 S1 O1 116.42(19) . . ?
C12 S1 F1 107.98(17) . . ?
C12 S1 C1 94.67(17) . . ?
C13 B1 C13 102.7(4) . 2_655 ?
C19 B1 C13 113.55(16) 2_655 . ?
C19 B1 C13 113.81(16) . . ?
C19 B1 C13 113.55(16) . 2_655 ?
C19 B1 C13 113.81(16) 2_655 2_655 ?
C19 B1 C19 99.9(4) 2_655 . ?
C2 C1 S1 126.6(3) . . ?
C6 C1 S1 109.9(3) . . ?
C6 C1 C2 123.5(3) . . ?
H2 C2 C1 121.6(2) . . ?
C3 C2 C1 116.9(3) . . ?
C3 C2 H2 121.6(2) . . ?
H3 C3 C2 119.7(2) . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7(2) . . ?
H4 C4 C3 119.2(2) . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2(2) . . ?
H5 C5 C4 120.3(2) . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 120.3(2) . . ?
C5 C6 C1 118.1(3) . . ?
C7 C6 C1 112.9(3) . . ?
C7 C6 C5 129.0(3) . . ?
C8 C7 C6 128.8(3) . . ?
C12 C7 C6 112.7(3) . . ?
C12 C7 C8 118.5(3) . . ?
H8 C8 C7 120.3(2) . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 H8 120.3(2) . . ?
H9 C9 C8 119.4(2) . . ?
C10 C9 C8 121.2(4) . . ?
C10 C9 H9 119.4(2) . . ?
H10 C10 C9 119.7(2) . . ?
C11 C10 C9 120.5(4) . . ?
C11 C10 H10 119.7(2) . . ?
H11 C11 C10 121.3(2) . . ?
C12 C11 C10 117.5(4) . . ?
C12 C11 H11 121.3(2) . . ?
C7 C12 S1 109.8(3) . . ?
C11 C12 S1 127.3(3) . . ?
C11 C12 C7 122.8(4) . . ?
C14 C13 B1 118.3(3) . 2_655 ?
C18 C13 B1 128.0(3) . 2_655 ?
C18 C13 C14 113.4(3) . . ?
C13 C14 F6 119.2(3) . . ?
C15 C14 F6 116.3(3) . . ?
C15 C14 C13 124.5(3) . . ?
C14 C15 F5 121.2(3) . . ?
C16 C15 F5 119.6(3) . . ?
C16 C15 C14 119.2(3) . . ?
C15 C16 F4 120.1(3) . . ?
C17 C16 F4 120.9(3) . . ?
C17 C16 C15 119.0(3) . . ?
C16 C17 F3 119.5(3) . . ?
C18 C17 F3 120.5(3) . . ?
C18 C17 C16 120.0(3) . . ?
C13 C18 F2 121.3(3) . . ?
C17 C18 F2 114.9(3) . . ?
C17 C18 C13 123.8(3) . . ?
C20 C19 B1 126.5(3) . . ?
C24 C19 B1 119.7(3) . . ?
C24 C19 C20 113.0(3) . . ?
C19 C20 F11 120.9(3) . . ?
C21 C20 F11 115.2(3) . . ?
C21 C20 C19 123.9(3) . . ?
C20 C21 F10 120.4(3) . . ?
C22 C21 F10 119.2(3) . . ?
C22 C21 C20 120.4(3) . . ?
C21 C22 F9 120.9(3) . . ?
C23 C22 F9 120.4(3) . . ?
C23 C22 C21 118.7(3) . . ?
C22 C23 F8 119.4(3) . . ?
C24 C23 F8 121.6(3) . . ?
C24 C23 C22 119.0(3) . . ?
C19 C24 F7 119.2(3) . . ?
C23 C24 F7 115.8(3) . . ?
C23 C24 C19 125.0(3) . . ?

_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_AW011_0m
_database_code_depnum_ccdc_archive 'CCDC 1500273'
_audit_update_record             
;
2016-08-20 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 B F5 O S'
_chemical_formula_weight         306.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.9113(7)
_cell_length_b                   10.7857(9)
_cell_length_c                   16.5078(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.049(7)
_cell_angle_gamma                90
_cell_volume                     1215.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2120
_cell_measurement_theta_min      4.528
_cell_measurement_theta_max      40.014

_exptl_crystal_description       shard
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   0.6997
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.320
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
'SADABS. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex II CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23694
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.264
_diffrn_reflns_theta_max         27.568
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2799
_reflns_number_gt                1751
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+1.2898P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2799
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.016
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16686(11) 0.38861(6) 0.92493(5) 0.0252(2) Uani 1 1 d . U . . .
O1 O 0.2326(3) 0.45214(19) 0.99941(12) 0.0334(5) Uani 1 1 d . U . . .
F1 F 0.0320(2) 0.47595(15) 0.86935(11) 0.0342(4) Uani 1 1 d . . . . .
F2 F 0.3421(3) 0.66555(16) 0.89017(11) 0.0392(5) Uani 1 1 d . . . . .
F3 F 0.5781(3) 0.79689(17) 0.95020(11) 0.0420(5) Uani 1 1 d . . . . .
F4 F 0.6044(3) 0.7026(2) 0.83012(14) 0.0621(7) Uani 1 1 d . . . . .
F5 F 0.3799(4) 0.85304(18) 0.83447(14) 0.0666(7) Uani 1 1 d . . . . .
B1 B 0.4769(5) 0.7550(3) 0.8758(2) 0.0259(8) Uani 1 1 d . . . . .
C1 C 0.3346(4) 0.3335(2) 0.86600(16) 0.0207(6) Uani 1 1 d . . . . .
C2 C 0.4874(4) 0.3976(3) 0.84030(17) 0.0243(7) Uani 1 1 d . . . . .
H2A H 0.5168 0.4811 0.8561 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5951(4) 0.3328(3) 0.79014(17) 0.0234(7) Uani 1 1 d . . . . .
H3A H 0.7018 0.3723 0.7707 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5495(4) 0.2110(3) 0.76786(17) 0.0241(7) Uani 1 1 d . . . . .
H4A H 0.6251 0.1692 0.7330 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3960(4) 0.1484(3) 0.79515(16) 0.0225(6) Uani 1 1 d . . . . .
H5A H 0.3677 0.0648 0.7796 0.027 Uiso 1 1 calc R U . . .
C6 C 0.2851(4) 0.2102(2) 0.84531(16) 0.0187(6) Uani 1 1 d . . . . .
C7 C 0.1143(4) 0.1647(2) 0.87989(16) 0.0192(6) Uani 1 1 d . . . . .
C8 C 0.0262(4) 0.0492(3) 0.87146(17) 0.0247(7) Uani 1 1 d . . . . .
H8A H 0.0765 -0.0140 0.8405 0.030 Uiso 1 1 calc R U . . .
C9 C -0.1375(4) 0.0270(3) 0.90905(18) 0.0293(7) Uani 1 1 d . . . . .
H9A H -0.2005 -0.0514 0.9020 0.035 Uiso 1 1 calc R U . . .
C10 C -0.2109(4) 0.1165(3) 0.95650(18) 0.0286(7) Uani 1 1 d . . . . .
H10A H -0.3214 0.0979 0.9820 0.034 Uiso 1 1 calc R U . . .
C11 C -0.1246(4) 0.2327(3) 0.96704(18) 0.0276(7) Uani 1 1 d . . . . .
H11A H -0.1721 0.2949 0.9996 0.033 Uiso 1 1 calc R U . . .
C12 C 0.0345(4) 0.2527(3) 0.92741(16) 0.0204(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.418(2) . ?
S1 F1 1.5261(18) . ?
S1 C12 1.731(3) . ?
S1 C1 1.732(3) . ?
F2 B1 1.388(4) . ?
F3 B1 1.390(4) . ?
F4 B1 1.369(4) . ?
F5 B1 1.374(4) . ?
C1 C2 1.384(4) . ?
C1 C6 1.402(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.386(4) . ?
C4 C5 1.391(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.474(4) . ?
C7 C8 1.384(4) . ?
C7 C12 1.399(4) . ?
C8 C9 1.394(4) . ?
C9 C10 1.388(4) . ?
C10 C11 1.387(4) . ?
C11 C12 1.382(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
O1 S1 F1 107.76(12) . . ?
O1 S1 C12 119.13(13) . . ?
F1 S1 C12 105.17(12) . . ?
O1 S1 C1 120.08(14) . . ?
F1 S1 C1 105.90(12) . . ?
C12 S1 C1 97.21(13) . . ?
F4 B1 F5 110.5(3) . . ?
F4 B1 F2 108.3(3) . . ?
F5 B1 F2 109.4(3) . . ?
F4 B1 F3 110.1(3) . . ?
F5 B1 F3 109.1(3) . . ?
F2 B1 F3 109.4(3) . . ?
C2 C1 C6 124.6(3) . . ?
C2 C1 S1 127.7(2) . . ?
C6 C1 S1 107.6(2) . . ?
C1 C2 C3 116.0(3) . . ?
C4 C3 C2 121.0(3) . . ?
C3 C4 C5 121.8(3) . . ?
C6 C5 C4 118.8(3) . . ?
C5 C6 C1 117.7(3) . . ?
C5 C6 C7 128.6(2) . . ?
C1 C6 C7 113.6(2) . . ?
C8 C7 C12 117.5(3) . . ?
C8 C7 C6 128.8(3) . . ?
C12 C7 C6 113.7(2) . . ?
C7 C8 C9 119.0(3) . . ?
C10 C9 C8 121.7(3) . . ?
C11 C10 C9 120.7(3) . . ?
C12 C11 C10 116.1(3) . . ?
C11 C12 C7 124.9(3) . . ?
C11 C12 S1 127.3(2) . . ?
C7 C12 S1 107.76(19) . . ?

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
O1 S1 C1 C2 -50.2(3) . . . . ?
F1 S1 C1 C2 71.9(3) . . . . ?
C12 S1 C1 C2 179.9(3) . . . . ?
O1 S1 C1 C6 131.8(2) . . . . ?
F1 S1 C1 C6 -106.1(2) . . . . ?
C12 S1 C1 C6 2.0(2) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
S1 C1 C2 C3 -177.1(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
S1 C1 C6 C5 177.5(2) . . . . ?
C2 C1 C6 C7 -179.2(3) . . . . ?
S1 C1 C6 C7 -1.2(3) . . . . ?
C5 C6 C7 C8 1.1(5) . . . . ?
C1 C6 C7 C8 179.6(3) . . . . ?
C5 C6 C7 C12 -179.0(3) . . . . ?
C1 C6 C7 C12 -0.5(3) . . . . ?
C12 C7 C8 C9 1.0(4) . . . . ?
C6 C7 C8 C9 -179.1(3) . . . . ?
C7 C8 C9 C10 -1.8(4) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C7 -1.3(4) . . . . ?
C10 C11 C12 S1 177.2(2) . . . . ?
C8 C7 C12 C11 0.5(4) . . . . ?
C6 C7 C12 C11 -179.4(3) . . . . ?
C8 C7 C12 S1 -178.2(2) . . . . ?
C6 C7 C12 S1 1.9(3) . . . . ?
O1 S1 C12 C11 48.6(3) . . . . ?
F1 S1 C12 C11 -72.3(3) . . . . ?
C1 S1 C12 C11 179.0(3) . . . . ?
O1 S1 C12 C7 -132.8(2) . . . . ?
F1 S1 C12 C7 106.39(19) . . . . ?
C1 S1 C12 C7 -2.3(2) . . . . ?

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.073



