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

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

data_sp014_0m
_database_code_depnum_ccdc_archive 'CCDC 1041085'
_audit_update_record             
;
2014-12-28 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_audit_creation_date             2014-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_formula_moiety         'C31 H22 B F15 N O3 P S, C7 H8'
_chemical_formula_sum            'C38 H30 B F15 N O3 P S'
_chemical_formula_weight         907.51
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'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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'
P 0.10434 0.09671 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'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      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                   8.2520(4)
_cell_length_b                   13.7632(7)
_cell_length_c                   17.0976(8)
_cell_angle_alpha                83.047(3)
_cell_angle_beta                 80.953(3)
_cell_angle_gamma                87.098(3)
_cell_volume                     1902.59(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9864
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.61
_cell_measurement_temperature    150
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0403 before and 0.0328 after correction.
The Ratio of minimum to maximum transmission is 0.9582.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5839
_exptl_crystal_density_meas      .
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             921.2410
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31528
_diffrn_reflns_theta_full        27.4484
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         1.49
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 0.9889
_diffrn_measured_fraction_theta_max 0.9889
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                7447
_reflns_number_total             8605
_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         0.8200
_refine_diff_density_min         -0.4974
_refine_diff_density_rms         0.0612
_refine_ls_d_res_high            0.7709
_refine_ls_d_res_low             13.6549
_refine_ls_goodness_of_fit_ref   1.0569
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     541
_refine_ls_number_reflns         8605
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.0569
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+1.4433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1070
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C22-C23
 1.54 with sigma of 0.02
3. Others
 Fixed Uiso: H20(0.06) H21(0.06) H23a(0.06) H23b(0.06) H23c(0.06) H25(0.06)
 H26a(0.06) H26b(0.06) H27a(0.06) H27b(0.06) H27c(0.06) H28a(0.06) H28b(0.06)
 H29a(0.06) H29b(0.06) H29c(0.06) H30a(0.06) H30b(0.06) H31a(0.06) H31b(0.06)
 H31c(0.06) H32a(0.06) H32b(0.06) H32c(0.06) H34(0.06) H35(0.06) H36(0.06)
 H37(0.06) H38(0.06)
4.a Secondary CH2 refined with riding coordinates:
 C26(H26a,H26b), C28(H28a,H28b), C30(H30a,H30b)
4.b Me refined with riding coordinates:
 C23(H23a,H23b,H23c), C27(H27a,H27b,H27c), C29(H29a,H29b,H29c), C31(H31a,H31b,
 H31c)
4.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C24(H24), C25(H25), C34(H34), C35(H35), C36(H36),
 C37(H37), C38(H38)
4.d Idealised Me refined as rotating group:
 C32(H32a,H32b,H32c)
;
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 0.35648(5) 0.31733(3) 0.21999(2) 0.02067(10) Uani 1.000000 .
P1 P 0.11885(5) 0.53545(3) 0.30550(2) 0.01921(10) Uani 1.000000 .
F1 F 0.08539(14) 0.27549(8) 0.10742(6) 0.0331(3) Uani 1.000000 .
F2 F -0.06859(17) 0.34282(10) -0.01303(7) 0.0476(3) Uani 1.000000 .
F3 F -0.31041(16) 0.48322(9) 0.00258(7) 0.0436(3) Uani 1.000000 .
F4 F -0.39463(13) 0.55746(8) 0.14533(7) 0.0337(3) Uani 1.000000 .
F5 F -0.24294(12) 0.49067(8) 0.26893(6) 0.0273(2) Uani 1.000000 .
F6 F -0.14218(13) 0.17139(7) 0.24745(6) 0.0268(2) Uani 1.000000 .
F7 F -0.38400(15) 0.07523(9) 0.34456(7) 0.0374(3) Uani 1.000000 .
F8 F -0.50613(14) 0.13670(9) 0.48782(7) 0.0387(3) Uani 1.000000 .
F9 F -0.38124(15) 0.29699(9) 0.53290(7) 0.0382(3) Uani 1.000000 .
F10 F -0.13614(15) 0.38923(8) 0.44259(6) 0.0355(3) Uani 1.000000 .
F11 F 0.18127(13) 0.24516(8) 0.42479(6) 0.0287(2) Uani 1.000000 .
F12 F 0.17685(15) 0.06573(9) 0.50868(7) 0.0393(3) Uani 1.000000 .
F13 F 0.18817(16) -0.09680(9) 0.43218(9) 0.0473(3) Uani 1.000000 .
F14 F 0.19601(17) -0.07930(8) 0.27182(9) 0.0456(3) Uani 1.000000 .
F15 F 0.18154(14) 0.09794(7) 0.18856(6) 0.0304(2) Uani 1.000000 .
O1 O 0.46395(15) 0.30414(10) 0.27933(8) 0.0286(3) Uani 1.000000 .
O2 O 0.32202(16) 0.41451(9) 0.18366(8) 0.0274(3) Uani 1.000000 .
O3 O 0.06731(14) 0.42917(8) 0.31281(6) 0.0202(2) Uani 1.000000 .
N1 N 0.17590(16) 0.27316(9) 0.25958(8) 0.0187(3) Uani 1.000000 .
C1 C -0.06438(19) 0.38220(11) 0.19476(9) 0.0193(3) Uani 1.000000 .
C2 C -0.0300(2) 0.34656(12) 0.12120(10) 0.0237(3) Uani 1.000000 .
C3 C -0.1106(2) 0.37977(14) 0.05693(10) 0.0294(4) Uani 1.000000 .
C4 C -0.2333(2) 0.45057(14) 0.06470(11) 0.0287(4) Uani 1.000000 .
C5 C -0.2752(2) 0.48729(12) 0.13689(11) 0.0246(3) Uani 1.000000 .
C6 C -0.1927(2) 0.45217(12) 0.19929(10) 0.0208(3) Uani 1.000000 .
C7 C -0.12328(19) 0.28508(11) 0.33905(9) 0.0186(3) Uani 1.000000 .
C8 C -0.1955(2) 0.20437(12) 0.31893(9) 0.0205(3) Uani 1.000000 .
C9 C -0.3209(2) 0.15342(13) 0.36748(10) 0.0243(3) Uani 1.000000 .
C10 C -0.3841(2) 0.18467(13) 0.43990(10) 0.0259(4) Uani 1.000000 .
C11 C -0.3204(2) 0.26524(13) 0.46242(10) 0.0250(3) Uani 1.000000 .
C12 C -0.1916(2) 0.31276(12) 0.41302(10) 0.0226(3) Uani 1.000000 .
C13 C 0.18411(19) 0.17852(11) 0.30352(10) 0.0203(3) Uani 1.000000 .
C14 C 0.1845(2) 0.16637(12) 0.38563(10) 0.0228(3) Uani 1.000000 .
C15 C 0.1831(2) 0.07483(14) 0.42924(11) 0.0282(4) Uani 1.000000 .
C16 C 0.1875(2) -0.00755(13) 0.39054(13) 0.0329(4) Uani 1.000000 .
C17 C 0.1908(2) 0.00110(13) 0.30937(12) 0.0304(4) Uani 1.000000 .
C18 C 0.1862(2) 0.09331(12) 0.26657(11) 0.0244(3) Uani 1.000000 .
C19 C 0.4465(2) 0.24871(12) 0.14244(10) 0.0231(3) Uani 1.000000 .
C20 C 0.5312(2) 0.16079(14) 0.15934(11) 0.0295(4) Uani 1.000000 .
H20 H 0.5427(2) 0.13695(14) 0.21275(11) 0.060000 Uiso 1.000000 R
C21 C 0.5986(2) 0.10832(15) 0.09704(13) 0.0343(4) Uani 1.000000 .
H21 H 0.6546(2) 0.04748(15) 0.10841(13) 0.060000 Uiso 1.000000 R
C22 C 0.5859(2) 0.14287(15) 0.01838(12) 0.0332(4) Uani 1.000000 D
C23 C 0.6528(3) 0.08353(17) -0.04922(14) 0.0465(6) Uani 1.000000 D
H23a H 0.6325(3) 0.11972(17) -0.09992(14) 0.060000 Uiso 1.000000 R
H23b H 0.7712(3) 0.07170(17) -0.05029(14) 0.060000 Uiso 1.000000 R
H23c H 0.5982(3) 0.02075(17) -0.04124(14) 0.060000 Uiso 1.000000 R
C24 C 0.5071(2) 0.23329(15) 0.00285(11) 0.0336(4) Uani 1.000000 .
H24 H 0.5015(2) 0.25918(15) -0.05078(11) 0.0404(5) Uiso 1.000000 R
C25 C 0.4365(2) 0.28631(14) 0.06415(11) 0.0294(4) Uani 1.000000 .
H25 H 0.3819(2) 0.34764(14) 0.05276(11) 0.060000 Uiso 1.000000 R
C26 C 0.1051(2) 0.60124(12) 0.20877(10) 0.0243(3) Uani 1.000000 .
H26a H 0.1292(2) 0.55455(12) 0.16840(10) 0.060000 Uiso 1.000000 R
H26b H -0.0094(2) 0.62623(12) 0.20826(10) 0.060000 Uiso 1.000000 R
C27 C 0.2192(3) 0.68705(14) 0.18375(12) 0.0350(4) Uani 1.000000 .
H27a H 0.2028(3) 0.71795(14) 0.13072(12) 0.060000 Uiso 1.000000 R
H27b H 0.1946(3) 0.73509(14) 0.22221(12) 0.060000 Uiso 1.000000 R
H27c H 0.3335(3) 0.66323(14) 0.18225(12) 0.060000 Uiso 1.000000 R
C28 C 0.3239(2) 0.53996(13) 0.32820(11) 0.0261(4) Uani 1.000000 .
H28a H 0.4026(2) 0.51775(13) 0.28347(11) 0.060000 Uiso 1.000000 R
H28b H 0.3475(2) 0.60878(13) 0.33248(11) 0.060000 Uiso 1.000000 R
C29 C 0.3520(3) 0.47707(15) 0.40544(11) 0.0332(4) Uani 1.000000 .
H29a H 0.4656(3) 0.48292(15) 0.41410(11) 0.060000 Uiso 1.000000 R
H29b H 0.2767(3) 0.49959(15) 0.45035(11) 0.060000 Uiso 1.000000 R
H29c H 0.3318(3) 0.40846(15) 0.40129(11) 0.060000 Uiso 1.000000 R
C30 C -0.0178(2) 0.59451(13) 0.37993(10) 0.0268(4) Uani 1.000000 .
H30a H -0.1322(2) 0.58622(13) 0.37173(10) 0.060000 Uiso 1.000000 R
H30b H -0.0049(2) 0.56045(13) 0.43313(10) 0.060000 Uiso 1.000000 R
C31 C 0.0084(3) 0.70386(14) 0.38016(12) 0.0374(5) Uani 1.000000 .
H31a H -0.0709(3) 0.72940(14) 0.42230(12) 0.060000 Uiso 1.000000 R
H31b H 0.1201(3) 0.71315(14) 0.38994(12) 0.060000 Uiso 1.000000 R
H31c H -0.0074(3) 0.73898(14) 0.32839(12) 0.060000 Uiso 1.000000 R
B1 B 0.0196(2) 0.34385(13) 0.27499(10) 0.0175(3) Uani 1.000000 .
C32 C 0.3882(5) 0.1725(3) 0.6787(2) 0.0838(10) Uani 1.000000 .
H32a H 0.3899(17) 0.2420(3) 0.6578(5) 0.060000 Uiso 1.000000 GR
H32b H 0.5002(7) 0.1481(12) 0.6835(3) 0.060000 Uiso 1.000000 GR
H32c H 0.3428(12) 0.1354(10) 0.6422(3) 0.060000 Uiso 1.000000 GR
C33 C 0.2852(3) 0.1604(2) 0.75775(17) 0.0533(6) Uani 1.000000 .
C34 C 0.1774(3) 0.08472(17) 0.77983(17) 0.0481(6) Uani 1.000000 .
H34 H 0.1683(3) 0.03982(17) 0.74281(17) 0.060000 Uiso 1.000000 R
C35 C 0.0840(3) 0.0728(2) 0.85309(18) 0.0575(7) Uani 1.000000 .
H35 H 0.0099(3) 0.0207(2) 0.86607(18) 0.060000 Uiso 1.000000 R
C36 C 0.0961(3) 0.1363(2) 0.90921(19) 0.0648(8) Uani 1.000000 .
H36 H 0.0350(3) 0.1270(2) 0.96134(19) 0.060000 Uiso 1.000000 R
C37 C 0.2008(4) 0.2135(3) 0.8860(2) 0.0849(12) Uani 1.000000 .
H37 H 0.2086(4) 0.2592(3) 0.9226(2) 0.060000 Uiso 1.000000 R
C38 C 0.2918(4) 0.2258(2) 0.8131(2) 0.0729(10) Uani 1.000000 .
H38 H 0.3617(4) 0.2799(2) 0.7992(2) 0.060000 Uiso 1.000000 R


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 1.4391(13) . ?
S1 O2 1.4393(13) . ?
S1 N1 1.6502(14) . ?
S1 C19 1.7674(17) . ?
P1 O3 1.5291(11) . ?
P1 C26 1.8040(17) . ?
P1 C28 1.8003(18) . ?
P1 C30 1.8049(17) . ?
F1 C2 1.345(2) . ?
F2 C3 1.345(2) . ?
F3 C4 1.343(2) . ?
F4 C5 1.348(2) . ?
F5 C6 1.3586(19) . ?
F6 C8 1.3558(19) . ?
F7 C9 1.3437(19) . ?
F8 C10 1.3410(19) . ?
F9 C11 1.345(2) . ?
F10 C12 1.3503(19) . ?
F11 C14 1.339(2) . ?
F12 C15 1.342(2) . ?
F13 C16 1.343(2) . ?
F14 C17 1.340(2) . ?
F15 C18 1.334(2) . ?
O3 B1 1.504(2) . ?
N1 C13 1.427(2) . ?
N1 B1 1.584(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.394(2) . ?
C1 B1 1.651(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.372(3) . ?
C4 C5 1.378(3) . ?
C5 C6 1.380(2) . ?
C7 C8 1.390(2) . ?
C7 C12 1.390(2) . ?
C7 B1 1.649(2) . ?
C8 C9 1.384(2) . ?
C9 C10 1.376(3) . ?
C10 C11 1.371(3) . ?
C11 C12 1.387(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.396(2) . ?
C14 C15 1.384(2) . ?
C15 C16 1.376(3) . ?
C16 C17 1.375(3) . ?
C17 C18 1.388(2) . ?
C19 C20 1.389(2) . ?
C19 C25 1.389(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(3) . ?
C22 C23 1.513(3) . ?
C22 C24 1.391(3) . ?
C23 H23a 0.9800 . ?
C23 H23b 0.9800 . ?
C23 H23c 0.9800 . ?
C24 H24 0.9500 . ?
C24 C25 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26a 0.9900 . ?
C26 H26b 0.9900 . ?
C26 C27 1.526(2) . ?
C27 H27a 0.9800 . ?
C27 H27b 0.9800 . ?
C27 H27c 0.9800 . ?
C28 H28a 0.9900 . ?
C28 H28b 0.9900 . ?
C28 C29 1.532(3) . ?
C29 H29a 0.9800 . ?
C29 H29b 0.9800 . ?
C29 H29c 0.9800 . ?
C30 H30a 0.9900 . ?
C30 H30b 0.9900 . ?
C30 C31 1.532(2) . ?
C31 H31a 0.9800 . ?
C31 H31b 0.9800 . ?
C31 H31c 0.9800 . ?
C32 H32a 0.9800 . ?
C32 H32b 0.9800 . ?
C32 H32c 0.9800 . ?
C32 C33 1.476(4) . ?
C33 C34 1.382(4) . ?
C33 C38 1.392(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.360(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.391(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.385(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.347(5) . ?
C38 H38 0.9500 . ?

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
O2 S1 O1 119.39(8) . . ?
N1 S1 O1 108.94(7) . . ?
N1 S1 O2 105.42(7) . . ?
C19 S1 O1 106.39(8) . . ?
C19 S1 O2 107.00(8) . . ?
C19 S1 N1 109.46(7) . . ?
C26 P1 O3 113.03(7) . . ?
C28 P1 O3 110.17(7) . . ?
C28 P1 C26 110.12(8) . . ?
C30 P1 O3 106.95(7) . . ?
C30 P1 C26 108.81(8) . . ?
C30 P1 C28 107.55(9) . . ?
B1 O3 P1 149.94(10) . . ?
C13 N1 S1 114.19(10) . . ?
B1 N1 S1 120.76(10) . . ?
B1 N1 C13 121.21(12) . . ?
C6 C1 C2 113.40(15) . . ?
B1 C1 C2 126.75(14) . . ?
B1 C1 C6 119.65(14) . . ?
C1 C2 F1 121.40(15) . . ?
C3 C2 F1 114.94(15) . . ?
C3 C2 C1 123.65(16) . . ?
C2 C3 F2 120.27(16) . . ?
C4 C3 F2 119.69(16) . . ?
C4 C3 C2 120.04(16) . . ?
C3 C4 F3 120.12(17) . . ?
C5 C4 F3 120.97(17) . . ?
C5 C4 C3 118.91(16) . . ?
C4 C5 F4 119.66(15) . . ?
C6 C5 F4 121.05(16) . . ?
C6 C5 C4 119.28(16) . . ?
C1 C6 F5 119.50(14) . . ?
C5 C6 F5 115.84(14) . . ?
C5 C6 C1 124.66(15) . . ?
C12 C7 C8 113.68(14) . . ?
B1 C7 C8 120.47(14) . . ?
B1 C7 C12 125.68(14) . . ?
C7 C8 F6 119.43(14) . . ?
C9 C8 F6 116.22(14) . . ?
C9 C8 C7 124.36(15) . . ?
C8 C9 F7 121.23(16) . . ?
C10 C9 F7 119.51(15) . . ?
C10 C9 C8 119.25(15) . . ?
C9 C10 F8 120.32(16) . . ?
C11 C10 F8 120.53(16) . . ?
C11 C10 C9 119.15(15) . . ?
C10 C11 F9 119.90(15) . . ?
C12 C11 F9 120.23(16) . . ?
C12 C11 C10 119.87(16) . . ?
C7 C12 F10 121.89(14) . . ?
C11 C12 F10 114.46(15) . . ?
C11 C12 C7 123.65(15) . . ?
C14 C13 N1 121.89(15) . . ?
C18 C13 N1 121.38(15) . . ?
C18 C13 C14 116.69(15) . . ?
C13 C14 F11 119.68(14) . . ?
C15 C14 F11 118.16(16) . . ?
C15 C14 C13 122.13(16) . . ?
C14 C15 F12 120.68(18) . . ?
C16 C15 F12 119.84(16) . . ?
C16 C15 C14 119.47(17) . . ?
C15 C16 F13 119.97(18) . . ?
C17 C16 F13 119.78(18) . . ?
C17 C16 C15 120.25(16) . . ?
C16 C17 F14 120.08(16) . . ?
C18 C17 F14 120.10(18) . . ?
C18 C17 C16 119.81(17) . . ?
C13 C18 F15 120.83(15) . . ?
C17 C18 F15 117.58(16) . . ?
C17 C18 C13 121.58(17) . . ?
C20 C19 S1 120.58(14) . . ?
C25 C19 S1 118.71(13) . . ?
C25 C19 C20 120.66(16) . . ?
H20 C20 C19 120.50(11) . . ?
C21 C20 C19 119.00(18) . . ?
C21 C20 H20 120.50(12) . . ?
H21 C21 C20 119.30(12) . . ?
C22 C21 C20 121.40(18) . . ?
C22 C21 H21 119.30(11) . . ?
C23 C22 C21 121.4(2) . . ?
C24 C22 C21 118.39(17) . . ?
C24 C22 C23 120.2(2) . . ?
H23a C23 C22 109.5 . . ?
H23b C23 C22 109.5 . . ?
H23b C23 H23a 109.5 . . ?
H23c C23 C22 109.5 . . ?
H23c C23 H23a 109.5 . . ?
H23c C23 H23b 109.5 . . ?
H24 C24 C22 119.38(11) . . ?
C25 C24 C22 121.23(18) . . ?
C25 C24 H24 119.38(12) . . ?
C24 C25 C19 119.21(17) . . ?
H25 C25 C19 120.39(10) . . ?
H25 C25 C24 120.39(12) . . ?
H26a C26 P1 108.40(6) . . ?
H26b C26 P1 108.40(6) . . ?
H26b C26 H26a 107.5 . . ?
C27 C26 P1 115.53(13) . . ?
C27 C26 H26a 108.40(11) . . ?
C27 C26 H26b 108.40(11) . . ?
H27a C27 C26 109.5 . . ?
H27b C27 C26 109.5 . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 C26 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?
H28a C28 P1 108.80(6) . . ?
H28b C28 P1 108.80(6) . . ?
H28b C28 H28a 107.7 . . ?
C29 C28 P1 113.80(13) . . ?
C29 C28 H28a 108.80(10) . . ?
C29 C28 H28b 108.80(10) . . ?
H29a C29 C28 109.5 . . ?
H29b C29 C28 109.5 . . ?
H29b C29 H29a 109.5 . . ?
H29c C29 C28 109.5 . . ?
H29c C29 H29a 109.5 . . ?
H29c C29 H29b 109.5 . . ?
H30a C30 P1 108.44(6) . . ?
H30b C30 P1 108.44(6) . . ?
H30b C30 H30a 107.5 . . ?
C31 C30 P1 115.33(13) . . ?
C31 C30 H30a 108.44(11) . . ?
C31 C30 H30b 108.44(11) . . ?
H31a C31 C30 109.5 . . ?
H31b C31 C30 109.5 . . ?
H31b C31 H31a 109.5 . . ?
H31c C31 C30 109.5 . . ?
H31c C31 H31a 109.5 . . ?
H31c C31 H31b 109.5 . . ?
N1 B1 O3 108.25(12) . . ?
C1 B1 O3 110.75(12) . . ?
C1 B1 N1 114.44(13) . . ?
C7 B1 O3 107.64(12) . . ?
C7 B1 N1 108.97(12) . . ?
C7 B1 C1 106.57(12) . . ?
H32b C32 H32a 109.5 . . ?
H32c C32 H32a 109.5 . . ?
H32c C32 H32b 109.5 . . ?
C33 C32 H32a 109.5 . . ?
C33 C32 H32b 109.5 . . ?
C33 C32 H32c 109.5 . . ?
C34 C33 C32 121.8(3) . . ?
C38 C33 C32 121.0(3) . . ?
C38 C33 C34 117.2(3) . . ?
H34 C34 C33 119.10(16) . . ?
C35 C34 C33 121.8(2) . . ?
C35 C34 H34 119.10(16) . . ?
H35 C35 C34 119.68(16) . . ?
C36 C35 C34 120.6(3) . . ?
C36 C35 H35 119.68(19) . . ?
H36 C36 C35 121.34(19) . . ?
C37 C36 C35 117.3(3) . . ?
C37 C36 H36 121.34(19) . . ?
H37 C37 C36 119.07(19) . . ?
C38 C37 C36 121.9(3) . . ?
C38 C37 H37 119.07(18) . . ?
C37 C38 C33 121.1(3) . . ?
H38 C38 C33 119.44(19) . . ?
H38 C38 C37 119.44(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C22 C23 1 1.5400 0.0200 0.0267

####################################################################### 
# 
# 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_SP007_0M
_database_code_depnum_ccdc_archive 'CCDC 1041086'
_audit_update_record             
;
2014-12-28 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_audit_creation_date             2014-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_formula_moiety         'C19 H8 B F10 N O2 S'
_chemical_formula_sum            'C19 H8 B F10 N O2 S'
_chemical_formula_weight         515.16
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'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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      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                   8.3826(6)
_cell_length_b                   11.3424(8)
_cell_length_c                   11.4015(8)
_cell_angle_alpha                101.452(4)
_cell_angle_beta                 92.380(4)
_cell_angle_gamma                111.680(4)
_cell_volume                     979.42(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6287
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.37
_cell_measurement_temperature    150
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0459 before and 0.0361 after correction.
The Ratio of minimum to maximum transmission is 0.9292.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.7466
_exptl_crystal_density_meas      .
_exptl_crystal_description       needle
_exptl_crystal_F_000             512.7399
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14021
_diffrn_reflns_theta_full        27.4363
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         1.84
_diffrn_ambient_temperature      149.4
_diffrn_measured_fraction_theta_full 0.9812
_diffrn_measured_fraction_theta_max 0.9812
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3171
_reflns_number_total             4394
_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         0.3958
_refine_diff_density_min         -0.4144
_refine_diff_density_rms         0.0856
_refine_ls_d_res_high            0.7713
_refine_ls_d_res_low             11.0853
_refine_ls_goodness_of_fit_ref   1.0459
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.0459
_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)+(0.0403P)²+0.3554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0959
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C5(H5a,H5b,H5c)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C2(H2), 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
S1 S 0.40692(7) 0.51229(5) 0.18776(5) 0.03089(14) Uani 1.000000 .
F1 F 0.50599(14) 0.80160(11) -0.02095(11) 0.0347(3) Uani 1.000000 .
F2 F 0.45500(16) 0.94035(12) -0.17221(11) 0.0421(3) Uani 1.000000 .
F3 F 0.15591(17) 0.97917(12) -0.18984(11) 0.0453(3) Uani 1.000000 .
F4 F -0.10231(15) 0.86655(12) -0.06148(11) 0.0391(3) Uani 1.000000 .
F5 F -0.05874(14) 0.72186(12) 0.08554(11) 0.0381(3) Uani 1.000000 .
F6 F -0.06299(16) 0.47605(11) 0.17202(11) 0.0405(3) Uani 1.000000 .
F7 F -0.19189(16) 0.47700(13) 0.38455(13) 0.0490(4) Uani 1.000000 .
F8 F -0.02864(19) 0.67698(14) 0.57859(11) 0.0514(4) Uani 1.000000 .
F9 F 0.26281(19) 0.87887(13) 0.55790(12) 0.0538(4) Uani 1.000000 .
F10 F 0.39284(15) 0.87710(11) 0.34436(11) 0.0393(3) Uani 1.000000 .
O1 O 0.2535(2) 0.41851(13) 0.21465(13) 0.0370(4) Uani 1.000000 .
O2 O 0.5282(2) 0.46930(16) 0.12536(13) 0.0451(4) Uani 1.000000 .
N1 N 0.3544(2) 0.59896(16) 0.10249(14) 0.0297(4) Uani 1.000000 .
H1 H 0.3952(2) 0.59850(16) 0.03262(14) 0.0356(5) Uiso 1.000000 R
C1 C 0.5173(2) 0.62641(19) 0.32167(18) 0.0274(4) Uani 1.000000 .
C2 C 0.6669(3) 0.7337(2) 0.3190(2) 0.0377(5) Uani 1.000000 .
H2 H 0.7099(3) 0.7460(2) 0.2446(2) 0.0452(6) Uiso 1.000000 R
C3 C 0.7513(3) 0.8214(2) 0.4254(2) 0.0409(5) Uani 1.000000 .
H3 H 0.8526(3) 0.8950(2) 0.4237(2) 0.0491(7) Uiso 1.000000 R
C4 C 0.6918(3) 0.8050(2) 0.5359(2) 0.0344(5) Uani 1.000000 .
C5 C 0.7855(3) 0.8997(2) 0.6530(2) 0.0523(7) Uani 1.000000 .
H5a H 0.8867(3) 0.9698(2) 0.6367(2) 0.0784(10) Uiso 1.000000 R
H5b H 0.7075(3) 0.9368(2) 0.6926(2) 0.0784(10) Uiso 1.000000 R
H5c H 0.8232(3) 0.8540(2) 0.7058(2) 0.0784(10) Uiso 1.000000 R
C6 C 0.5432(3) 0.6966(2) 0.53620(19) 0.0325(5) Uani 1.000000 .
H6 H 0.5013(3) 0.6833(2) 0.61064(19) 0.0390(6) Uiso 1.000000 R
C7 C 0.4550(3) 0.60786(19) 0.43014(18) 0.0288(4) Uani 1.000000 .
H7 H 0.3528(3) 0.53490(19) 0.43164(18) 0.0345(5) Uiso 1.000000 R
C8 C 0.2252(2) 0.75440(17) 0.03909(16) 0.0236(4) Uani 1.000000 .
C9 C 0.3514(2) 0.81211(17) -0.03083(17) 0.0247(4) Uani 1.000000 .
C10 C 0.3283(3) 0.88507(18) -0.10817(17) 0.0299(4) Uani 1.000000 .
C11 C 0.1768(3) 0.90472(19) -0.11794(17) 0.0305(5) Uani 1.000000 .
C12 C 0.0466(3) 0.84894(18) -0.05164(18) 0.0291(4) Uani 1.000000 .
C13 C 0.0735(2) 0.77587(18) 0.02465(17) 0.0263(4) Uani 1.000000 .
C14 C 0.1697(2) 0.67612(17) 0.25191(17) 0.0236(4) Uani 1.000000 .
C15 C 0.0209(2) 0.57663(18) 0.26640(18) 0.0279(4) Uani 1.000000 .
C16 C -0.0471(3) 0.5760(2) 0.37455(19) 0.0325(5) Uani 1.000000 .
C17 C 0.0353(3) 0.6778(2) 0.47237(18) 0.0339(5) Uani 1.000000 .
C18 C 0.1820(3) 0.7801(2) 0.46205(18) 0.0332(5) Uani 1.000000 .
C19 C 0.2463(2) 0.77780(18) 0.35212(18) 0.0268(4) Uani 1.000000 .
B1 B 0.2521(3) 0.6729(2) 0.12914(19) 0.0240(5) 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 1.4249(15) . ?
S1 O2 1.4372(15) . ?
S1 N1 1.6642(16) . ?
S1 C1 1.754(2) . ?
F1 C9 1.347(2) . ?
F2 C10 1.345(2) . ?
F3 C11 1.337(2) . ?
F4 C12 1.339(2) . ?
F5 C13 1.348(2) . ?
F6 C15 1.346(2) . ?
F7 C16 1.343(2) . ?
F8 C17 1.345(2) . ?
F9 C18 1.341(2) . ?
F10 C19 1.346(2) . ?
N1 B1 1.408(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.386(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.394(3) . ?
C4 C5 1.508(3) . ?
C4 C6 1.391(3) . ?
C6 C7 1.384(3) . ?
C8 C9 1.396(3) . ?
C8 C13 1.390(3) . ?
C8 B1 1.572(3) . ?
C9 C10 1.376(3) . ?
C10 C11 1.372(3) . ?
C11 C12 1.382(3) . ?
C12 C13 1.379(3) . ?
C14 C15 1.381(3) . ?
C14 C19 1.384(3) . ?
C14 B1 1.586(3) . ?
C15 C16 1.380(3) . ?
C16 C17 1.375(3) . ?
C17 C18 1.373(3) . ?
C18 C19 1.384(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
O2 S1 O1 119.56(9) . . ?
N1 S1 O1 109.58(9) . . ?
N1 S1 O2 104.81(8) . . ?
C1 S1 O1 108.83(9) . . ?
C1 S1 O2 108.56(10) . . ?
C1 S1 N1 104.44(9) . . ?
B1 N1 S1 127.56(14) . . ?
C2 C1 S1 120.28(16) . . ?
C7 C1 S1 119.19(15) . . ?
C7 C1 C2 120.5(2) . . ?
C3 C2 C1 119.1(2) . . ?
C4 C3 C2 121.6(2) . . ?
C5 C4 C3 121.8(2) . . ?
C6 C4 C3 118.2(2) . . ?
C6 C4 C5 120.0(2) . . ?
C7 C6 C4 121.23(19) . . ?
C6 C7 C1 119.38(18) . . ?
C13 C8 C9 114.91(17) . . ?
B1 C8 C9 123.01(17) . . ?
B1 C8 C13 122.07(16) . . ?
C8 C9 F1 120.02(17) . . ?
C10 C9 F1 117.10(16) . . ?
C10 C9 C8 122.83(18) . . ?
C9 C10 F2 120.55(18) . . ?
C11 C10 F2 119.49(18) . . ?
C11 C10 C9 119.94(17) . . ?
C10 C11 F3 120.22(18) . . ?
C12 C11 F3 120.01(19) . . ?
C12 C11 C10 119.76(18) . . ?
C11 C12 F4 120.17(18) . . ?
C13 C12 F4 120.97(17) . . ?
C13 C12 C11 118.86(18) . . ?
C8 C13 F5 119.90(17) . . ?
C12 C13 F5 116.41(17) . . ?
C12 C13 C8 123.69(17) . . ?
C19 C14 C15 116.11(17) . . ?
B1 C14 C15 122.30(17) . . ?
B1 C14 C19 121.57(16) . . ?
C14 C15 F6 119.43(17) . . ?
C16 C15 F6 118.00(17) . . ?
C16 C15 C14 122.57(18) . . ?
C15 C16 F7 120.51(19) . . ?
C17 C16 F7 120.19(18) . . ?
C17 C16 C15 119.31(18) . . ?
C16 C17 F8 119.67(19) . . ?
C18 C17 F8 119.97(19) . . ?
C18 C17 C16 120.35(18) . . ?
C17 C18 F9 120.20(18) . . ?
C19 C18 F9 120.99(19) . . ?
C19 C18 C17 118.80(18) . . ?
C14 C19 F10 119.06(17) . . ?
C18 C19 F10 118.06(17) . . ?
C18 C19 C14 122.84(18) . . ?
C8 B1 N1 119.83(17) . . ?
C14 B1 N1 119.41(17) . . ?
C14 B1 C8 120.74(16) . . ?

_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_sp015_0ma
_database_code_depnum_ccdc_archive 'CCDC 1041087'
_audit_update_record             
;
2014-12-28 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_audit_creation_date             2014-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_formula_moiety         'C18 H5 B Cl F10 N O2 S'
_chemical_formula_sum            'C18 H5 B Cl F10 N O2 S'
_chemical_formula_weight         535.57
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'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'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'
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'
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'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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      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                   8.3755(3)
_cell_length_b                   11.2582(5)
_cell_length_c                   11.2869(4)
_cell_angle_alpha                76.807(3)
_cell_angle_beta                 87.603(2)
_cell_angle_gamma                68.315(2)
_cell_volume                     961.79(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9905
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.40
_cell_measurement_temperature    150
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0471 before and 0.0328 after correction.
The Ratio of minimum to maximum transmission is 0.9484.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.8491
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             529.0338
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16138
_diffrn_reflns_theta_full        27.4831
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.86
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3779
_reflns_number_total             4413
_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         0.3947
_refine_diff_density_min         -0.3546
_refine_diff_density_rms         0.0617
_refine_ls_d_res_high            0.7700
_refine_ls_d_res_low             10.9769
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    10
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.0660
_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)+(0.0386P)²+0.4322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0849
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C15(H15), C14(H14), N1(H1)
;
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
Cl1 Cl 0.38123(6) 0.93216(5) -0.16117(5) 0.04415(13) Uani 1.000000 .
S1 S 0.39278(5) 0.51430(4) 0.31046(3) 0.02665(11) Uani 1.000000 .
F1 F 0.20421(11) 0.80242(9) 0.52225(9) 0.0297(2) Uani 1.000000 .
F2 F 0.01606(14) 0.94256(10) 0.67548(9) 0.0366(2) Uani 1.000000 .
F3 F -0.32225(14) 0.98340(11) 0.69344(10) 0.0408(3) Uani 1.000000 .
F4 F -0.46897(12) 0.86812(10) 0.56604(9) 0.0361(2) Uani 1.000000 .
F5 F -0.28245(12) 0.72270(10) 0.41648(9) 0.0346(2) Uani 1.000000 .
F6 F -0.04358(14) 0.47635(10) 0.33062(9) 0.0362(2) Uani 1.000000 .
F7 F -0.17559(14) 0.47532(11) 0.11749(10) 0.0421(3) Uani 1.000000 .
F8 F -0.21084(14) 0.67436(12) -0.07966(9) 0.0445(3) Uani 1.000000 .
F9 F -0.11586(15) 0.87658(11) -0.06189(9) 0.0463(3) Uani 1.000000 .
F10 F 0.01844(12) 0.87632(9) 0.15173(9) 0.0335(2) Uani 1.000000 .
O1 O 0.33179(16) 0.42246(11) 0.27885(11) 0.0334(3) Uani 1.000000 .
O2 O 0.55700(15) 0.46877(13) 0.37366(11) 0.0389(3) Uani 1.000000 .
N1 N 0.25391(16) 0.60008(13) 0.39761(12) 0.0264(3) Uani 1.000000 .
H1 H 0.29536(16) 0.59920(13) 0.46831(12) 0.0317(3) Uiso 1.000000 R
C1 C -0.03027(19) 0.75572(14) 0.46222(13) 0.0209(3) Uani 1.000000 .
C2 C 0.03896(19) 0.81330(14) 0.53279(13) 0.0218(3) Uani 1.000000 .
C3 C -0.0562(2) 0.88752(15) 0.61129(14) 0.0259(3) Uani 1.000000 .
C4 C -0.2277(2) 0.90734(15) 0.62139(14) 0.0276(3) Uani 1.000000 .
C5 C -0.3027(2) 0.85058(15) 0.55532(14) 0.0264(3) Uani 1.000000 .
C6 C -0.2039(2) 0.77718(15) 0.47796(14) 0.0239(3) Uani 1.000000 .
C7 C -0.00825(18) 0.67638(14) 0.24776(13) 0.0210(3) Uani 1.000000 .
C8 C -0.06005(19) 0.57640(15) 0.23457(14) 0.0243(3) Uani 1.000000 .
C9 C -0.1281(2) 0.57474(16) 0.12628(15) 0.0279(3) Uani 1.000000 .
C10 C -0.1466(2) 0.67606(18) 0.02632(14) 0.0294(4) Uani 1.000000 .
C11 C -0.0995(2) 0.77846(16) 0.03556(14) 0.0285(3) Uani 1.000000 .
C12 C -0.03204(19) 0.77750(15) 0.14589(14) 0.0232(3) Uani 1.000000 .
C13 C 0.39100(19) 0.63240(15) 0.17780(14) 0.0241(3) Uani 1.000000 .
C14 C 0.3491(2) 0.61596(16) 0.06632(14) 0.0256(3) Uani 1.000000 .
H14 H 0.3221(2) 0.54206(16) 0.06224(14) 0.0307(4) Uiso 1.000000 R
C15 C 0.3471(2) 0.70867(17) -0.03882(15) 0.0286(3) Uani 1.000000 .
H15 H 0.3198(2) 0.69877(17) -0.11598(15) 0.0343(4) Uiso 1.000000 R
C16 C 0.3854(2) 0.81604(17) -0.02967(16) 0.0303(4) Uani 1.000000 .
C17 C 0.4280(2) 0.83226(18) 0.08164(17) 0.0347(4) Uani 1.000000 .
H17 H 0.4544(2) 0.90640(18) 0.08578(17) 0.0416(5) Uiso 1.000000 R
C18 C 0.4315(2) 0.73958(17) 0.18580(16) 0.0317(4) Uani 1.000000 .
H18 H 0.4614(2) 0.74872(17) 0.26261(16) 0.0380(4) Uiso 1.000000 R
B1 B 0.0775(2) 0.67397(16) 0.37108(15) 0.0210(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
Cl1 C16 1.7315(18) . ?
S1 O1 1.4252(12) . ?
S1 O2 1.4344(12) . ?
S1 N1 1.6616(13) . ?
S1 C13 1.7574(17) . ?
F1 C2 1.3462(17) . ?
F2 C3 1.3391(17) . ?
F3 C4 1.3359(18) . ?
F4 C5 1.3367(18) . ?
F5 C6 1.3496(17) . ?
F6 C8 1.3428(18) . ?
F7 C9 1.3431(18) . ?
F8 C10 1.3390(17) . ?
F9 C11 1.3398(18) . ?
F10 C12 1.3431(17) . ?
N1 H1 0.8800 . ?
N1 B1 1.407(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.394(2) . ?
C1 B1 1.569(2) . ?
C2 C3 1.380(2) . ?
C3 C4 1.374(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.376(2) . ?
C7 C8 1.386(2) . ?
C7 C12 1.383(2) . ?
C7 B1 1.583(2) . ?
C8 C9 1.377(2) . ?
C9 C10 1.377(2) . ?
C10 C11 1.375(2) . ?
C11 C12 1.385(2) . ?
C13 C14 1.390(2) . ?
C13 C18 1.391(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C16 C17 1.389(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(3) . ?
C18 H18 0.9500 . ?

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
O2 S1 O1 119.87(8) . . ?
N1 S1 O1 109.95(7) . . ?
N1 S1 O2 105.03(7) . . ?
C13 S1 O1 108.65(7) . . ?
C13 S1 O2 108.18(8) . . ?
C13 S1 N1 104.02(7) . . ?
H1 N1 S1 116.35(4) . . ?
B1 N1 S1 127.31(11) . . ?
B1 N1 H1 116.35(8) . . ?
C6 C1 C2 114.82(13) . . ?
B1 C1 C2 122.91(13) . . ?
B1 C1 C6 122.27(13) . . ?
C1 C2 F1 119.95(13) . . ?
C3 C2 F1 116.86(13) . . ?
C3 C2 C1 123.13(14) . . ?
C2 C3 F2 120.71(14) . . ?
C4 C3 F2 119.82(14) . . ?
C4 C3 C2 119.46(14) . . ?
C3 C4 F3 119.81(15) . . ?
C5 C4 F3 120.19(15) . . ?
C5 C4 C3 119.98(14) . . ?
C4 C5 F4 120.22(14) . . ?
C6 C5 F4 120.83(14) . . ?
C6 C5 C4 118.95(14) . . ?
C1 C6 F5 119.64(13) . . ?
C5 C6 F5 116.71(14) . . ?
C5 C6 C1 123.64(14) . . ?
C12 C7 C8 116.16(13) . . ?
B1 C7 C8 122.20(13) . . ?
B1 C7 C12 121.62(13) . . ?
C7 C8 F6 119.25(13) . . ?
C9 C8 F6 118.05(14) . . ?
C9 C8 C7 122.70(15) . . ?
C8 C9 F7 120.65(15) . . ?
C10 C9 F7 120.03(14) . . ?
C10 C9 C8 119.32(15) . . ?
C9 C10 F8 119.65(16) . . ?
C11 C10 F8 120.29(16) . . ?
C11 C10 C9 120.06(14) . . ?
C10 C11 F9 120.17(14) . . ?
C12 C11 F9 120.59(15) . . ?
C12 C11 C10 119.23(15) . . ?
C7 C12 F10 119.23(13) . . ?
C11 C12 F10 118.20(14) . . ?
C11 C12 C7 122.51(14) . . ?
C14 C13 S1 118.77(12) . . ?
C18 C13 S1 119.89(12) . . ?
C18 C13 C14 121.34(16) . . ?
H14 C14 C13 120.39(10) . . ?
C15 C14 C13 119.21(15) . . ?
C15 C14 H14 120.39(9) . . ?
H15 C15 C14 120.51(9) . . ?
C16 C15 C14 118.99(15) . . ?
C16 C15 H15 120.51(10) . . ?
C15 C16 Cl1 118.81(13) . . ?
C17 C16 Cl1 119.36(13) . . ?
C17 C16 C15 121.83(16) . . ?
H17 C17 C16 120.43(10) . . ?
C18 C17 C16 119.14(16) . . ?
C18 C17 H17 120.43(10) . . ?
C17 C18 C13 119.48(15) . . ?
H18 C18 C13 120.26(10) . . ?
H18 C18 C17 120.26(10) . . ?
C1 B1 N1 119.64(13) . . ?
C7 B1 N1 119.42(13) . . ?
C7 B1 C1 120.92(13) . . ?

_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_sp009_0m
_database_code_depnum_ccdc_archive 'CCDC 1041088'
_audit_update_record             
;
2014-12-28 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_audit_creation_date             2014-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_formula_moiety         'C13 H4 B F10 N O2 S'
_chemical_formula_sum            'C13 H4 B F10 N O2 S'
_chemical_formula_weight         439.06
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'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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      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                   6.0068(7)
_cell_length_b                   9.6962(12)
_cell_length_c                   13.5918(15)
_cell_angle_alpha                74.330(7)
_cell_angle_beta                 81.758(7)
_cell_angle_gamma                85.914(7)
_cell_volume                     753.89(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3813
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.33
_cell_measurement_temperature    150
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0564 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.9368.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.9339
_exptl_crystal_density_meas      .
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             432.7083
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12448
_diffrn_reflns_theta_full        27.4224
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         1.57
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 0.9942
_diffrn_measured_fraction_theta_max 0.9942
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2286
_reflns_number_total             3427
_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         0.5706
_refine_diff_density_min         -0.6263
_refine_diff_density_rms         0.1488
_refine_ls_d_res_high            0.7716
_refine_ls_d_res_low             12.9769
_refine_ls_goodness_of_fit_ref   1.0313
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.0313
_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)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.1026
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C13(H13a,H13b,H13c)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
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 -0.03010(11) 0.75934(7) 0.49813(5) 0.01969(17) Uani 1.000000 .
F1 F 0.5624(3) 0.97510(15) 0.37317(11) 0.0270(4) Uani 1.000000 .
F2 F 0.8578(3) 1.16427(16) 0.25435(12) 0.0302(4) Uani 1.000000 .
F3 F 0.8170(3) 1.27829(16) 0.05163(12) 0.0349(4) Uani 1.000000 .
F4 F 0.4755(3) 1.20057(16) -0.03135(11) 0.0315(4) Uani 1.000000 .
F5 F 0.1795(3) 1.00767(15) 0.08665(11) 0.0276(4) Uani 1.000000 .
F6 F -0.1569(3) 0.80787(15) 0.19283(12) 0.0284(4) Uani 1.000000 .
F7 F -0.1550(3) 0.58207(16) 0.11228(12) 0.0304(4) Uani 1.000000 .
F8 F 0.1827(3) 0.37856(16) 0.13938(12) 0.0321(4) Uani 1.000000 .
F9 F 0.5100(3) 0.39734(15) 0.25354(12) 0.0321(4) Uani 1.000000 .
F10 F 0.5103(3) 0.62333(15) 0.33307(11) 0.0279(4) Uani 1.000000 .
O1 O -0.1493(3) 0.84079(18) 0.56432(13) 0.0257(4) Uani 1.000000 .
O2 O -0.1525(3) 0.66868(19) 0.46007(14) 0.0277(5) Uani 1.000000 .
N1 N 0.1034(4) 0.8776(2) 0.39955(15) 0.0194(5) Uani 1.000000 .
H1 H 0.1147(4) 0.9628(2) 0.40924(15) 0.0232(6) Uiso 1.000000 R
C1 C 0.3597(4) 0.9833(2) 0.23432(18) 0.0169(5) Uani 1.000000 .
C2 C 0.5343(4) 1.0295(2) 0.27318(18) 0.0187(6) Uani 1.000000 .
C3 C 0.6889(4) 1.1251(3) 0.21303(19) 0.0208(6) Uani 1.000000 .
C4 C 0.6700(4) 1.1822(3) 0.1104(2) 0.0222(6) Uani 1.000000 .
C5 C 0.4971(5) 1.1425(3) 0.06851(19) 0.0217(6) Uani 1.000000 .
C6 C 0.3475(4) 1.0436(3) 0.13033(19) 0.0193(6) Uani 1.000000 .
C7 C 0.1774(4) 0.7230(2) 0.26510(18) 0.0179(5) Uani 1.000000 .
C8 C 0.0097(4) 0.7068(3) 0.20932(19) 0.0193(6) Uani 1.000000 .
C9 C 0.0084(4) 0.5924(3) 0.16697(19) 0.0212(6) Uani 1.000000 .
C10 C 0.1786(4) 0.4880(3) 0.18145(19) 0.0209(6) Uani 1.000000 .
C11 C 0.3448(4) 0.4996(3) 0.23835(19) 0.0197(6) Uani 1.000000 .
C12 C 0.3413(4) 0.6147(3) 0.27848(18) 0.0191(6) Uani 1.000000 .
C13 C 0.1907(5) 0.6600(3) 0.5594(2) 0.0307(7) Uani 1.000000 .
H13a H 0.2746(5) 0.7227(3) 0.5855(2) 0.0461(10) Uiso 1.000000 R
H13b H 0.1290(5) 0.5819(3) 0.6170(2) 0.0461(10) Uiso 1.000000 R
H13c H 0.2919(5) 0.6201(3) 0.5100(2) 0.0461(10) Uiso 1.000000 R
B1 B 0.2007(5) 0.8618(3) 0.3034(2) 0.0187(6) 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 1.4368(18) . ?
S1 O2 1.4239(17) . ?
S1 N1 1.657(2) . ?
S1 C13 1.756(3) . ?
F1 C2 1.349(3) . ?
F2 C3 1.350(3) . ?
F3 C4 1.341(3) . ?
F4 C5 1.343(3) . ?
F5 C6 1.351(3) . ?
F6 C8 1.348(3) . ?
F7 C9 1.338(3) . ?
F8 C10 1.331(3) . ?
F9 C11 1.349(3) . ?
F10 C12 1.360(3) . ?
N1 H1 0.8800 . ?
N1 B1 1.396(4) . ?
C1 C2 1.390(3) . ?
C1 C6 1.387(3) . ?
C1 B1 1.577(4) . ?
C2 C3 1.374(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.377(3) . ?
C5 C6 1.380(4) . ?
C7 C8 1.386(3) . ?
C7 C12 1.381(4) . ?
C7 B1 1.590(4) . ?
C8 C9 1.382(3) . ?
C9 C10 1.383(4) . ?
C10 C11 1.375(3) . ?
C11 C12 1.366(3) . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 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
O2 S1 O1 119.12(11) . . ?
N1 S1 O1 105.94(11) . . ?
N1 S1 O2 109.18(10) . . ?
C13 S1 O1 108.67(12) . . ?
C13 S1 O2 109.67(12) . . ?
C13 S1 N1 103.03(12) . . ?
H1 N1 S1 115.25(7) . . ?
B1 N1 S1 129.50(18) . . ?
B1 N1 H1 115.25(14) . . ?
C6 C1 C2 115.3(2) . . ?
B1 C1 C2 121.3(2) . . ?
B1 C1 C6 123.2(2) . . ?
C1 C2 F1 119.8(2) . . ?
C3 C2 F1 117.3(2) . . ?
C3 C2 C1 122.9(2) . . ?
C2 C3 F2 120.5(2) . . ?
C4 C3 F2 119.9(2) . . ?
C4 C3 C2 119.7(2) . . ?
C3 C4 F3 120.1(2) . . ?
C5 C4 F3 120.2(2) . . ?
C5 C4 C3 119.7(2) . . ?
C4 C5 F4 119.8(2) . . ?
C6 C5 F4 120.9(2) . . ?
C6 C5 C4 119.3(2) . . ?
C1 C6 F5 119.4(2) . . ?
C5 C6 F5 117.6(2) . . ?
C5 C6 C1 123.1(2) . . ?
C12 C7 C8 115.6(2) . . ?
B1 C7 C8 124.0(2) . . ?
B1 C7 C12 120.2(2) . . ?
C7 C8 F6 119.3(2) . . ?
C9 C8 F6 118.0(2) . . ?
C9 C8 C7 122.7(2) . . ?
C8 C9 F7 120.7(2) . . ?
C10 C9 F7 120.0(2) . . ?
C10 C9 C8 119.3(2) . . ?
C9 C10 F8 120.1(2) . . ?
C11 C10 F8 120.5(2) . . ?
C11 C10 C9 119.3(2) . . ?
C10 C11 F9 119.6(2) . . ?
C12 C11 F9 120.7(2) . . ?
C12 C11 C10 119.7(2) . . ?
C7 C12 F10 118.6(2) . . ?
C11 C12 F10 118.0(2) . . ?
C11 C12 C7 123.4(2) . . ?
H13a C13 S1 109.5 . . ?
H13b C13 S1 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 S1 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
C1 B1 N1 117.3(2) . . ?
C7 B1 N1 123.6(2) . . ?
C7 B1 C1 118.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
