# 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_13S005
_database_code_depnum_ccdc_archive 'CCDC 1401858'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_date             2013-04-30
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_formula_moiety         'C H4 B11 F10 N, 0.5(H2 O)'
_chemical_formula_sum            'C H5 B11 F10 N O0.5'
_chemical_formula_weight         348.11
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 '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 '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 '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 '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 '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 '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           37
_space_group_name_H-M_alt        'C c c 2'
_space_group_name_Hall           'C 2 -2c'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z
3 -x,y,z+1/2
4 x,-y,z+1/2
5 x+1/2,y+1/2,z
6 -x+1/2,-y+1/2,z
7 -x+1/2,y+1/2,z+1/2
8 x+1/2,-y+1/2,z+1/2

_cell_length_a                   14.684(4)
_cell_length_b                   22.575(7)
_cell_length_c                   14.269(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4730(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    7045
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.70
_cell_measurement_theta_min      2.19
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1303 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.8919.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.9543
_exptl_crystal_density_meas      .
_exptl_crystal_description       plate
_exptl_crystal_F_000             2674.9061
_exptl_crystal_preparation       'soaked in perfluoro polyether oil'
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.077
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31184
_diffrn_reflns_theta_full        25.9988
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.65
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              27
_reflns_limit_k_min              -27
_reflns_limit_l_max              17
_reflns_limit_l_min              -17
_reflns_number_gt                4010
_reflns_number_total             4659
_reflns_threshold_expression     I>=2u(I)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.3410
_refine_diff_density_min         -0.2430
_refine_diff_density_rms         0.0649
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             12.3092
_refine_ls_goodness_of_fit_ref   1.0613
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     426
_refine_ls_number_reflns         4659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.0613
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.5304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0957
_refine_special_details          
'The water molecule O1W lies on a special position which causes flipping between two positions of the hydrogen atoms. Thus the maximum shift is still very high in the refinement, but the overall structure is static.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O2W(H2W), O1W(H1W)
2.b Idealised Me refined as rotating group:
 N1B(H1Ba,H1Bb,H1Bc), N1A(H1Aa,H1Ab,H1Ac)
2.c Boron cage BH refined with riding coordinates:
 C1A(H1A), C1B(H1B)
;
_atom_sites_solution_primary     direct
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
F3A F 0.45511(11) 0.69088(8) 0.57953(12) 0.0196(4) Uani 1.000000 . .
F8A F 0.57735(11) 0.81793(8) 0.55665(11) 0.0179(4) Uani 1.000000 . .
F7A F 0.68808(11) 0.80507(7) 0.36311(12) 0.0185(4) Uani 1.000000 . .
F4A F 0.32056(11) 0.68111(8) 0.41657(13) 0.0232(4) Uani 1.000000 . .
F6A F 0.54803(12) 0.79595(8) 0.19532(11) 0.0207(4) Uani 1.000000 . .
F9A F 0.35880(12) 0.81288(8) 0.50642(12) 0.0212(4) Uani 1.000000 . .
F2A F 0.65713(11) 0.68684(8) 0.49728(12) 0.0202(4) Uani 1.000000 . .
F10A F 0.34346(11) 0.80215(8) 0.27763(12) 0.0213(4) Uani 1.000000 . .
F11A F 0.49617(11) 0.87908(6) 0.36104(11) 0.0195(4) Uani 1.000000 . .
B11A B 0.5002(2) 0.81970(14) 0.3774(2) 0.0128(7) Uani 1.000000 . .
B7A B 0.6057(2) 0.77861(15) 0.3761(2) 0.0123(7) Uani 1.000000 . .
C1A C 0.50088(19) 0.67760(12) 0.4003(2) 0.0152(7) Uani 1.000000 . .
H1A H 0.50117(19) 0.62912(12) 0.4080(2) 0.0183(8) Uiso 1.000000 R .
B8A B 0.5426(2) 0.78549(15) 0.4840(2) 0.0137(7) Uani 1.000000 . .
B9A B 0.4209(2) 0.78329(16) 0.4543(2) 0.0148(8) Uani 1.000000 . .
B6A B 0.5258(2) 0.77217(14) 0.2800(2) 0.0126(7) Uani 1.000000 . .
B3A B 0.4764(2) 0.71863(15) 0.4986(2) 0.0153(7) Uani 1.000000 . .
B2A B 0.5904(2) 0.71583(16) 0.4512(2) 0.0126(8) Uani 1.000000 . .
B4A B 0.3966(2) 0.71263(16) 0.4027(2) 0.0162(7) Uani 1.000000 . .
B10A B 0.4114(2) 0.77479(16) 0.3280(2) 0.0157(8) Uani 1.000000 . .
F7B F 0.93455(10) 0.44714(7) 0.59326(13) 0.0195(4) Uani 1.000000 . .
F9B F 0.59415(12) 0.44107(8) 0.47846(13) 0.0225(4) Uani 1.000000 . .
F10B F 0.59698(11) 0.44773(8) 0.70790(12) 0.0209(4) Uani 1.000000 . .
F5B F 0.69134(12) 0.57942(8) 0.75885(11) 0.0242(4) Uani 1.000000 . .
F6B F 0.80940(12) 0.45185(8) 0.77314(11) 0.0222(4) Uani 1.000000 . .
F4B F 0.56436(10) 0.57251(7) 0.58047(12) 0.0218(4) Uani 1.000000 . .
F8B F 0.80754(12) 0.44022(8) 0.40809(12) 0.0208(4) Uani 1.000000 . .
F3B F 0.68342(12) 0.56710(8) 0.40641(11) 0.0208(4) Uani 1.000000 . .
N1B N 0.89732(16) 0.58137(11) 0.69538(17) 0.0179(6) Uani 1.000000 . .
H1Ba H 0.9302(9) 0.6012(6) 0.65343(17) 0.0215(7) Uiso 1.000000 GR .
H1Bb H 0.86829(17) 0.6069(6) 0.7324(10) 0.0215(7) Uiso 1.000000 GR .
H1Bc H 0.9339(8) 0.55870(13) 0.7298(10) 0.0215(7) Uiso 1.000000 GR .
F2B F 0.89168(12) 0.56731(8) 0.46947(12) 0.0216(4) Uani 1.000000 . .
B2B B 0.8283(2) 0.53743(17) 0.5195(2) 0.0147(8) Uani 1.000000 . .
B10B B 0.6614(2) 0.47546(15) 0.6541(2) 0.0141(8) Uani 1.000000 . .
F11B F 0.74247(10) 0.37243(6) 0.60725(11) 0.0209(4) Uani 1.000000 . .
B1B B 0.8277(2) 0.54234(17) 0.6446(2) 0.0146(7) Uani 1.000000 . .
B5B B 0.7127(2) 0.54391(15) 0.6866(2) 0.0147(7) Uani 1.000000 . .
B8B B 0.7787(2) 0.46898(14) 0.4861(2) 0.0136(7) Uani 1.000000 . .
C1B C 0.74470(17) 0.57468(12) 0.5803(2) 0.0158(6) Uani 1.000000 . .
H1B H 0.74493(17) 0.62332(12) 0.5758(2) 0.0189(7) Uiso 1.000000 R .
B4B B 0.6406(2) 0.53947(14) 0.5848(3) 0.0151(6) Uani 1.000000 . .
B6B B 0.7795(2) 0.47769(14) 0.6916(2) 0.0152(7) Uani 1.000000 . .
B7B B 0.8505(2) 0.47339(14) 0.5892(3) 0.0140(6) Uani 1.000000 . .
B3B B 0.7117(2) 0.53604(16) 0.4826(2) 0.0148(7) Uani 1.000000 . .
B9B B 0.6605(2) 0.47060(16) 0.5263(3) 0.0168(8) Uani 1.000000 . .
B11B B 0.7458(2) 0.43226(14) 0.5941(3) 0.0160(7) Uani 1.000000 . .
F5A F 0.43289(12) 0.66803(8) 0.22795(12) 0.0239(4) Uani 1.000000 . .
N1A N 0.64452(16) 0.66955(11) 0.27153(18) 0.0167(5) Uani 1.000000 . .
H1Aa H 0.6751(9) 0.69208(17) 0.2312(9) 0.0201(7) Uiso 1.000000 GR .
H1Ab H 0.6834(8) 0.6521(6) 0.3106(2) 0.0201(7) Uiso 1.000000 GR .
H1Ac H 0.6136(2) 0.6420(5) 0.2403(10) 0.0201(7) Uiso 1.000000 GR .
O2W O 0.250000 0.750000 0.6560(2) 0.0196(6) Uani 1.000000 S T
H2W H 0.222380 0.725670 0.6205(2) 0.0295(9) Uiso 1.000000 R .
O1W O 1.000000 0.500000 0.30804(18) 0.0189(6) Uani 1.000000 S T
H1W H 0.963490 0.519530 0.34243(18) 0.0283(9) Uiso 1.000000 R .
B5A B 0.4603(2) 0.70583(16) 0.2953(2) 0.0167(7) Uani 1.000000 . .
B1A B 0.5782(2) 0.70809(16) 0.3274(2) 0.0149(7) Uani 1.000000 . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F3A B3A 1.350(4) .
F8A B8A 1.368(4) .
F7A B7A 1.361(4) .
F4A B4A 1.338(4) .
F6A B6A 1.362(4) .
F9A B9A 1.353(4) .
F2A B2A 1.349(4) .
F10A B10A 1.376(4) .
F11A B11A 1.362(3) .
B11A B7A 1.806(5) .
B11A B8A 1.816(5) .
B11A B9A 1.800(5) .
B11A B6A 1.796(5) .
B11A B10A 1.796(5) .
B7A B8A 1.805(5) .
B7A B6A 1.810(5) .
B7A B2A 1.791(5) .
B7A B1A 1.783(5) .
C1A B3A 1.719(5) .
C1A B2A 1.732(4) .
C1A B4A 1.724(4) .
C1A B5A 1.734(5) .
C1A B1A 1.688(4) .
B8A B9A 1.837(5) .
B8A B3A 1.807(5) .
B8A B2A 1.785(5) .
B9A B3A 1.787(5) .
B9A B4A 1.793(5) .
B9A B10A 1.819(5) .
B6A B10A 1.815(5) .
B6A B5A 1.793(4) .
B6A B1A 1.772(5) .
B3A B2A 1.807(5) .
B3A B4A 1.807(5) .
B2A B1A 1.784(5) .
B4A B10A 1.776(5) .
B4A B5A 1.803(5) .
B10A B5A 1.777(5) .
F7B B7B 1.370(3) .
F9B B9B 1.364(4) .
F10B B10B 1.370(4) .
F5B B5B 1.343(4) .
F6B B6B 1.373(4) .
F4B B4B 1.347(4) .
F8B B8B 1.357(4) .
F3B B3B 1.359(4) .
N1B B1B 1.532(4) .
F2B B2B 1.353(4) .
B2B B1B 1.788(4) .
B2B B8B 1.774(5) .
B2B C1B 1.723(5) .
B2B B7B 1.785(5) .
B2B B3B 1.791(5) .
B10B B5B 1.780(5) .
B10B B4B 1.778(5) .
B10B B6B 1.816(5) .
B10B B9B 1.826(4) .
B10B B11B 1.793(5) .
F11B B11B 1.364(3) .
B1B B5B 1.793(5) .
B1B C1B 1.691(4) .
B1B B6B 1.755(5) .
B1B B7B 1.777(5) .
B5B C1B 1.732(4) .
B5B B4B 1.800(5) .
B5B B6B 1.790(4) .
B8B B7B 1.813(5) .
B8B B3B 1.806(5) .
B8B B9B 1.829(5) .
B8B B11B 1.816(5) .
C1B B4B 1.724(4) .
C1B B3B 1.714(4) .
B4B B3B 1.794(5) .
B4B B9B 1.788(5) .
B6B B7B 1.797(5) .
B6B B11B 1.798(5) .
B7B B11B 1.798(4) .
B3B B9B 1.771(5) .
B9B B11B 1.804(5) .
F5A B5A 1.347(4) .
N1A B1A 1.529(4) .
B5A B1A 1.791(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
B7A B11A F11A 122.8(3) . .
B8A B11A F11A 125.2(3) . .
B8A B11A B7A 59.78(18) . .
B9A B11A F11A 121.7(3) . .
B9A B11A B7A 109.1(2) . .
B9A B11A B8A 61.1(2) . .
B6A B11A F11A 117.7(3) . .
B6A B11A B7A 60.34(18) . .
B6A B11A B8A 108.8(2) . .
B6A B11A B9A 109.6(2) . .
B10A B11A F11A 117.2(3) . .
B10A B11A B7A 109.2(2) . .
B10A B11A B8A 109.7(2) . .
B10A B11A B9A 60.76(19) . .
B10A B11A B6A 60.71(18) . .
B11A B7A F7A 122.5(3) . .
B8A B7A F7A 122.3(2) . .
B8A B7A B11A 60.39(18) . .
B6A B7A F7A 120.6(2) . .
B6A B7A B11A 59.54(18) . .
B6A B7A B8A 108.7(2) . .
B2A B7A F7A 122.7(2) . .
B2A B7A B11A 107.0(2) . .
B2A B7A B8A 59.52(18) . .
B2A B7A B6A 107.9(2) . .
B1A B7A F7A 122.7(3) . .
B1A B7A B11A 105.6(2) . .
B1A B7A B8A 107.0(2) . .
B1A B7A B6A 59.10(18) . .
B1A B7A B2A 59.89(19) . .
B2A C1A B3A 63.15(19) . .
B4A C1A B3A 63.32(19) . .
B4A C1A B2A 115.9(2) . .
B5A C1A B3A 115.8(2) . .
B5A C1A B2A 116.1(2) . .
B5A C1A B4A 62.85(19) . .
B1A C1A B3A 115.1(2) . .
B1A C1A B2A 62.89(19) . .
B1A C1A B4A 115.0(2) . .
B1A C1A B5A 63.12(19) . .
B11A B8A F8A 122.3(2) . .
B7A B8A F8A 120.1(3) . .
B7A B8A B11A 59.83(18) . .
B9A B8A F8A 123.5(3) . .
B9A B8A B11A 59.02(19) . .
B9A B8A B7A 107.5(2) . .
B3A B8A F8A 124.1(2) . .
B3A B8A B11A 105.5(2) . .
B3A B8A B7A 107.6(2) . .
B3A B8A B9A 58.73(19) . .
B2A B8A F8A 121.6(2) . .
B2A B8A B11A 106.8(2) . .
B2A B8A B7A 59.86(18) . .
B2A B8A B9A 107.4(2) . .
B2A B8A B3A 60.39(19) . .
B11A B9A F9A 123.1(3) . .
B8A B9A F9A 121.0(3) . .
B8A B9A B11A 59.90(18) . .
B3A B9A F9A 121.1(3) . .
B3A B9A B11A 107.1(2) . .
B3A B9A B8A 59.79(19) . .
B4A B9A F9A 122.1(3) . .
B4A B9A B11A 106.5(2) . .
B4A B9A B8A 108.2(2) . .
B4A B9A B3A 60.6(2) . .
B10A B9A F9A 123.1(3) . .
B10A B9A B11A 59.51(19) . .
B10A B9A B8A 107.8(2) . .
B10A B9A B3A 107.4(3) . .
B10A B9A B4A 58.9(2) . .
B11A B6A F6A 120.1(2) . .
B7A B6A F6A 119.0(2) . .
B7A B6A B11A 60.12(18) . .
B10A B6A F6A 122.9(3) . .
B10A B6A B11A 59.65(18) . .
B10A B6A B7A 108.2(2) . .
B5A B6A F6A 124.4(2) . .
B5A B6A B11A 107.0(2) . .
B5A B6A B7A 108.8(2) . .
B5A B6A B10A 59.01(19) . .
B1A B6A F6A 123.8(3) . .
B1A B6A B11A 106.5(2) . .
B1A B6A B7A 59.69(18) . .
B1A B6A B10A 106.5(2) . .
B1A B6A B5A 60.32(18) . .
C1A B3A F3A 119.7(2) . .
B8A B3A F3A 127.7(3) . .
B8A B3A C1A 104.1(2) . .
B9A B3A F3A 125.1(3) . .
B9A B3A C1A 104.3(2) . .
B9A B3A B8A 61.48(19) . .
B2A B3A F3A 121.3(3) . .
B2A B3A C1A 58.77(18) . .
B2A B3A B8A 59.19(18) . .
B2A B3A B9A 108.6(2) . .
B4A B3A F3A 117.5(3) . .
B4A B3A C1A 58.48(18) . .
B4A B3A B8A 108.9(2) . .
B4A B3A B9A 59.83(19) . .
B4A B3A B2A 108.3(2) . .
B7A B2A F2A 125.7(3) . .
C1A B2A F2A 120.9(3) . .
C1A B2A B7A 103.8(2) . .
B8A B2A F2A 125.8(3) . .
B8A B2A B7A 60.63(19) . .
B8A B2A C1A 104.5(2) . .
B3A B2A F2A 120.5(3) . .
B3A B2A B7A 108.2(2) . .
B3A B2A C1A 58.08(18) . .
B3A B2A B8A 60.41(19) . .
B1A B2A F2A 120.5(3) . .
B1A B2A B7A 59.83(19) . .
B1A B2A C1A 57.34(19) . .
B1A B2A B8A 107.9(2) . .
B1A B2A B3A 106.4(2) . .
C1A B4A F4A 120.0(3) . .
B9A B4A F4A 125.3(3) . .
B9A B4A C1A 103.8(2) . .
B3A B4A F4A 118.0(3) . .
B3A B4A C1A 58.20(18) . .
B3A B4A B9A 59.53(19) . .
B10A B4A F4A 127.7(3) . .
B10A B4A C1A 104.0(2) . .
B10A B4A B9A 61.3(2) . .
B10A B4A B3A 108.4(2) . .
B5A B4A F4A 120.9(3) . .
B5A B4A C1A 58.84(18) . .
B5A B4A B9A 108.8(2) . .
B5A B4A B3A 108.3(2) . .
B5A B4A B10A 59.5(2) . .
B11A B10A F10A 118.6(3) . .
B9A B10A F10A 121.7(3) . .
B9A B10A B11A 59.7(2) . .
B6A B10A F10A 119.3(3) . .
B6A B10A B11A 59.64(18) . .
B6A B10A B9A 107.9(2) . .
B4A B10A F10A 125.4(3) . .
B4A B10A B11A 107.4(2) . .
B4A B10A B9A 59.8(2) . .
B4A B10A B6A 108.3(2) . .
B5A B10A F10A 123.3(3) . .
B5A B10A B11A 107.7(2) . .
B5A B10A B9A 108.8(2) . .
B5A B10A B6A 59.88(18) . .
B5A B10A B4A 60.99(19) . .
B1B B2B F2B 120.0(3) . .
B8B B2B F2B 125.1(3) . .
B8B B2B B1B 108.7(3) . .
C1B B2B F2B 120.8(3) . .
C1B B2B B1B 57.6(2) . .
C1B B2B B8B 105.5(2) . .
B7B B2B F2B 124.9(3) . .
B7B B2B B1B 59.7(2) . .
B7B B2B B8B 61.3(2) . .
B7B B2B C1B 104.2(2) . .
B3B B2B F2B 120.7(3) . .
B3B B2B B1B 106.8(3) . .
B3B B2B B8B 60.86(19) . .
B3B B2B C1B 58.36(18) . .
B3B B2B B7B 108.9(2) . .
B5B B10B F10B 122.8(3) . .
B4B B10B F10B 124.4(3) . .
B4B B10B B5B 60.77(19) . .
B6B B10B F10B 120.5(3) . .
B6B B10B B5B 59.70(18) . .
B6B B10B B4B 107.8(2) . .
B9B B10B F10B 121.8(3) . .
B9B B10B B5B 108.4(2) . .
B9B B10B B4B 59.5(2) . .
B9B B10B B6B 107.7(3) . .
B11B B10B F10B 119.7(3) . .
B11B B10B B5B 107.7(2) . .
B11B B10B B4B 107.2(2) . .
B11B B10B B6B 59.77(19) . .
B11B B10B B9B 59.8(2) . .
B2B B1B N1B 120.3(3) . .
B5B B1B N1B 117.3(3) . .
B5B B1B B2B 109.8(3) . .
C1B B1B N1B 119.3(3) . .
C1B B1B B2B 59.3(2) . .
C1B B1B B5B 59.54(18) . .
B6B B1B N1B 124.5(3) . .
B6B B1B B2B 109.4(3) . .
B6B B1B B5B 60.58(19) . .
B6B B1B C1B 106.0(2) . .
B7B B1B N1B 126.0(3) . .
B7B B1B B2B 60.1(2) . .
B7B B1B B5B 110.1(3) . .
B7B B1B C1B 105.8(2) . .
B7B B1B B6B 61.2(2) . .
B10B B5B F5B 128.3(3) . .
B1B B5B F5B 119.2(3) . .
B1B B5B B10B 107.1(2) . .
C1B B5B F5B 119.7(3) . .
C1B B5B B10B 103.6(2) . .
C1B B5B B1B 57.31(17) . .
B4B B5B F5B 121.1(2) . .
B4B B5B B10B 59.54(18) . .
B4B B5B B1B 106.5(2) . .
B4B B5B C1B 58.38(17) . .
B6B B5B F5B 126.5(2) . .
B6B B5B B10B 61.13(19) . .
B6B B5B B1B 58.7(2) . .
B6B B5B C1B 102.8(2) . .
B6B B5B B4B 108.0(2) . .
B2B B8B F8B 120.6(3) . .
B7B B8B F8B 120.7(3) . .
B7B B8B B2B 59.67(18) . .
B3B B8B F8B 123.3(2) . .
B3B B8B B2B 60.06(19) . .
B3B B8B B7B 107.0(2) . .
B9B B8B F8B 124.3(3) . .
B9B B8B B2B 106.7(2) . .
B9B B8B B7B 107.2(2) . .
B9B B8B B3B 58.33(19) . .
B11B B8B F8B 124.1(3) . .
B11B B8B B2B 106.2(2) . .
B11B B8B B7B 59.41(18) . .
B11B B8B B3B 105.1(2) . .
B11B B8B B9B 59.32(18) . .
B1B C1B B2B 63.15(17) . .
B5B C1B B2B 116.0(2) . .
B5B C1B B1B 63.15(19) . .
B4B C1B B2B 115.2(2) . .
B4B C1B B1B 114.8(2) . .
B4B C1B B5B 62.76(19) . .
B3B C1B B2B 62.8(2) . .
B3B C1B B1B 115.1(2) . .
B3B C1B B5B 115.5(2) . .
B3B C1B B4B 62.92(19) . .
B10B B4B F4B 128.2(3) . .
B5B B4B F4B 119.6(3) . .
B5B B4B B10B 59.7(2) . .
C1B B4B F4B 118.7(2) . .
C1B B4B B10B 104.1(2) . .
C1B B4B B5B 58.85(18) . .
B3B B4B F4B 118.1(3) . .
B3B B4B B10B 108.5(2) . .
B3B B4B B5B 108.4(2) . .
B3B B4B C1B 58.29(18) . .
B9B B4B F4B 126.6(3) . .
B9B B4B B10B 61.60(17) . .
B9B B4B B5B 109.2(2) . .
B9B B4B C1B 103.9(2) . .
B9B B4B B3B 59.27(19) . .
B10B B6B F6B 122.9(3) . .
B1B B6B F6B 123.2(3) . .
B1B B6B B10B 107.2(2) . .
B5B B6B F6B 124.3(2) . .
B5B B6B B10B 59.16(19) . .
B5B B6B B1B 60.75(18) . .
B7B B6B F6B 118.7(2) . .
B7B B6B B10B 108.2(2) . .
B7B B6B B1B 60.02(19) . .
B7B B6B B5B 109.3(2) . .
B11B B6B F6B 120.1(3) . .
B11B B6B B10B 59.50(18) . .
B11B B6B B1B 106.8(2) . .
B11B B6B B5B 107.1(2) . .
B11B B6B B7B 60.03(18) . .
B2B B7B F7B 122.6(3) . .
B1B B7B F7B 122.0(3) . .
B1B B7B B2B 60.25(18) . .
B8B B7B F7B 122.3(3) . .
B8B B7B B2B 59.07(19) . .
B8B B7B B1B 107.4(2) . .
B6B B7B F7B 120.8(3) . .
B6B B7B B2B 107.6(2) . .
B6B B7B B1B 58.82(19) . .
B6B B7B B8B 109.0(2) . .
B11B B7B F7B 123.0(2) . .
B11B B7B B2B 106.5(2) . .
B11B B7B B1B 105.9(2) . .
B11B B7B B8B 60.36(18) . .
B11B B7B B6B 60.01(19) . .
B2B B3B F3B 121.2(3) . .
B8B B3B F3B 128.4(2) . .
B8B B3B B2B 59.1(2) . .
C1B B3B F3B 118.3(3) . .
C1B B3B B2B 58.81(18) . .
C1B B3B B8B 104.5(2) . .
B4B B3B F3B 116.7(3) . .
B4B B3B B2B 108.5(2) . .
B4B B3B B8B 109.3(2) . .
B4B B3B C1B 58.79(17) . .
B9B B3B F3B 125.6(3) . .
B9B B3B B2B 108.5(2) . .
B9B B3B B8B 61.5(2) . .
B9B B3B C1B 105.0(2) . .
B9B B3B B4B 60.19(19) . .
B10B B9B F9B 122.3(3) . .
B8B B9B F9B 120.7(3) . .
B8B B9B B10B 107.9(3) . .
B4B B9B F9B 122.8(3) . .
B4B B9B B10B 58.9(2) . .
B4B B9B B8B 108.6(2) . .
B3B B9B F9B 122.3(3) . .
B3B B9B B10B 107.3(3) . .
B3B B9B B8B 60.19(19) . .
B3B B9B B4B 60.54(19) . .
B11B B9B F9B 122.0(3) . .
B11B B9B B10B 59.2(2) . .
B11B B9B B8B 59.98(19) . .
B11B B9B B4B 106.3(3) . .
B11B B9B B3B 107.1(2) . .
F11B B11B B10B 116.6(2) . .
B8B B11B B10B 109.9(2) . .
B8B B11B F11B 125.3(3) . .
B6B B11B B10B 60.7(2) . .
B6B B11B F11B 117.9(3) . .
B6B B11B B8B 108.8(2) . .
B7B B11B B10B 109.2(2) . .
B7B B11B F11B 123.1(2) . .
B7B B11B B8B 60.22(18) . .
B7B B11B B6B 59.96(19) . .
B9B B11B B10B 61.01(17) . .
B9B B11B F11B 121.6(2) . .
B9B B11B B8B 60.7(2) . .
B9B B11B B6B 109.4(2) . .
B9B B11B B7B 109.0(2) . .
B6A B5A C1A 103.2(2) . .
B4A B5A C1A 58.31(18) . .
B4A B5A B6A 108.1(2) . .
B10A B5A C1A 103.5(2) . .
B10A B5A B6A 61.11(19) . .
B10A B5A B4A 59.49(19) . .
F5A B5A C1A 119.1(3) . .
F5A B5A B6A 127.1(3) . .
F5A B5A B4A 120.3(3) . .
F5A B5A B10A 128.4(3) . .
B1A B5A C1A 57.17(18) . .
B1A B5A B6A 59.27(19) . .
B1A B5A B4A 106.4(2) . .
B1A B5A B10A 107.4(2) . .
B1A B5A F5A 119.3(3) . .
C1A B1A B7A 106.0(2) . .
B6A B1A B7A 61.21(19) . .
B6A B1A C1A 106.0(2) . .
B2A B1A B7A 60.3(2) . .
B2A B1A C1A 59.76(19) . .
B2A B1A B6A 109.9(3) . .
N1A B1A B7A 124.5(3) . .
N1A B1A C1A 121.2(3) . .
N1A B1A B6A 122.8(3) . .
N1A B1A B2A 120.5(3) . .
B5A B1A B7A 110.1(2) . .
B5A B1A C1A 59.71(19) . .
B5A B1A B6A 60.41(19) . .
B5A B1A B2A 110.6(2) . .
B5A B1A N1A 117.7(3) . .

####################################################################### 
# 
# 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_7H3NHCB11F10
_database_code_depnum_ccdc_archive 'CCDC 1401859'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;


#=================================================================
#DATA 1
#================================================================= 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C H4 B11 F10 N, C6 H14 O3'
_chemical_formula_sum            'C7 H18 B11 F10 N O3'
_chemical_formula_weight         473.13

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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                   8.647(5)
_cell_length_b                   14.863(7)
_cell_length_c                   15.435(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.148(18)
_cell_angle_gamma                90
_cell_volume                     1978.5(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2912
_cell_measurement_theta_min      2.6235
_cell_measurement_theta_max      26.008

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.4519
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2012/1 (Bruker 2012)'

_exptl_special_details           
;
  The crystal was immersed in a film of perfluoropolyether oil, mounted
on a polyimide microloop (MicroMounts of MiTeGen) and transferred to
stream of cold nitrogen (Oxford Cryostream 700). 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10659
_diffrn_reflns_av_unetI/netI     0.0983
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3626
_reflns_number_gt                2056
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. 8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0169P)²+3.6200P] 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         3626
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.1797
_refine_ls_wR_factor_gt          0.1521
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_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
C1 C 0.4613(6) 0.5418(3) 0.3501(3) 0.0281(11) Uani 1 1 d . . . . .
H1 H 0.4880(15) 0.586(2) 0.393(2) 0.039(14) Uiso 1 1 calc R . . . .
B2 B 0.3069(7) 0.4723(3) 0.3670(3) 0.0258(13) Uani 1 1 d . . . . .
F2 F 0.2264(3) 0.48097(17) 0.43927(17) 0.0345(7) Uani 1 1 d . . . . .
B3 B 0.2946(7) 0.5584(4) 0.2855(4) 0.0334(15) Uani 1 1 d . . . . .
F3 F 0.2077(3) 0.63372(17) 0.29582(17) 0.0383(7) Uani 1 1 d . . . . .
B4 B 0.4795(7) 0.5714(4) 0.2432(3) 0.0307(14) Uani 1 1 d . . . . .
F4 F 0.5258(4) 0.65672(18) 0.22576(18) 0.0437(8) Uani 1 1 d . . . . .
B5 B 0.6112(7) 0.4928(4) 0.2997(4) 0.0308(14) Uani 1 1 d . . . . .
F5 F 0.7589(3) 0.51911(19) 0.32110(18) 0.0407(8) Uani 1 1 d . . . . .
B6 B 0.5041(6) 0.4321(3) 0.3752(3) 0.0256(12) Uani 1 1 d . . . . .
F6 F 0.5736(3) 0.41119(17) 0.45449(16) 0.0313(7) Uani 1 1 d . . . . .
B7 B 0.2251(7) 0.4473(4) 0.2605(3) 0.0293(13) Uani 1 1 d . . . . .
F7 F 0.0722(3) 0.42626(17) 0.24408(17) 0.0334(7) Uani 1 1 d . . . . .
B8 B 0.3337(7) 0.5092(4) 0.1842(3) 0.0305(14) Uani 1 1 d . . . . .
F8 F 0.2632(4) 0.54127(18) 0.10731(17) 0.0421(8) Uani 1 1 d . . . . .
B9 B 0.5298(7) 0.4689(4) 0.1919(3) 0.0296(13) Uani 1 1 d . . . . .
F9 F 0.6184(4) 0.46547(18) 0.12156(17) 0.0407(8) Uani 1 1 d . . . . .
B10 B 0.5439(7) 0.3813(4) 0.2751(3) 0.0301(14) Uani 1 1 d . . . . .
F10 F 0.6412(3) 0.30940(17) 0.26985(17) 0.0340(7) Uani 1 1 d . . . . .
B11 B 0.3577(6) 0.3695(3) 0.3171(3) 0.0243(12) Uani 1 1 d . . . . .
N1 N 0.3010(4) 0.2776(2) 0.3460(2) 0.0243(9) Uani 1 1 d . . . . .
H1A H 0.2600 0.2475 0.3001 0.036 Uiso 1 1 calc R U . . .
H1B H 0.2294 0.2851 0.3841 0.036 Uiso 1 1 calc R U . . .
H1C H 0.3805 0.2466 0.3708 0.036 Uiso 1 1 calc R U . . .
B12 B 0.3719(7) 0.3926(4) 0.2037(4) 0.0296(13) Uani 1 1 d . . . . .
F12 F 0.3348(3) 0.32705(17) 0.14366(16) 0.0319(7) Uani 1 1 d . . . . .
O1 O 0.0673(4) 0.2887(2) 0.4579(2) 0.0365(9) Uani 1 1 d . . . . .
C2 C -0.0762(6) 0.3268(4) 0.4257(4) 0.0540(17) Uani 1 1 d . . . . .
H2A H -0.0882 0.3196 0.3637 0.081 Uiso 1 1 calc R U . . .
H2B H -0.0777 0.3896 0.4399 0.081 Uiso 1 1 calc R U . . .
H2C H -0.1597 0.2968 0.4516 0.081 Uiso 1 1 calc R U . . .
C3 C 0.1006(7) 0.3091(4) 0.5483(3) 0.0477(15) Uani 1 1 d . . . . .
H3A H 0.0117 0.2947 0.5806 0.057 Uiso 1 1 calc R U . . .
H3B H 0.1228 0.3728 0.5555 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2365(7) 0.2552(4) 0.5813(3) 0.0494(16) Uani 1 1 d . . . . .
H4A H 0.2510 0.2615 0.6439 0.059 Uiso 1 1 calc R U . . .
H4B H 0.2177 0.1922 0.5681 0.059 Uiso 1 1 calc R U . . .
O2 O 0.3729(4) 0.2840(2) 0.5430(2) 0.0334(8) Uani 1 1 d . . . . .
C5 C 0.5056(7) 0.2305(3) 0.5673(3) 0.0455(16) Uani 1 1 d . . . . .
H5A H 0.5000 0.2110 0.6270 0.055 Uiso 1 1 calc R U . . .
H5B H 0.5977 0.2674 0.5649 0.055 Uiso 1 1 calc R U . . .
C6 C 0.5216(7) 0.1496(3) 0.5114(3) 0.0489(17) Uani 1 1 d . . . . .
H6A H 0.6103 0.1141 0.5330 0.059 Uiso 1 1 calc R U . . .
H6B H 0.4296 0.1124 0.5121 0.059 Uiso 1 1 calc R U . . .
O3 O 0.5417(4) 0.1793(2) 0.4254(2) 0.0415(10) Uani 1 1 d . . . . .
C7 C 0.6087(7) 0.1126(4) 0.3727(4) 0.0588(18) Uani 1 1 d . . . . .
H7A H 0.6069 0.1337 0.3138 0.088 Uiso 1 1 calc R U . . .
H7B H 0.5503 0.0579 0.3747 0.088 Uiso 1 1 calc R U . . .
H7C H 0.7140 0.1017 0.3942 0.088 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 B6 1.709(7) . ?
C1 B3 1.710(7) . ?
C1 B5 1.720(8) . ?
C1 B2 1.722(7) . ?
C1 B4 1.726(7) . ?
C1 H1 0.95(5) . ?
B2 F2 1.363(6) . ?
B2 B11 1.779(7) . ?
B2 B7 1.781(7) . ?
B2 B3 1.792(7) . ?
B2 B6 1.802(8) . ?
B3 F3 1.364(6) . ?
B3 B4 1.781(9) . ?
B3 B8 1.781(8) . ?
B3 B7 1.789(8) . ?
B4 F4 1.363(6) . ?
B4 B8 1.763(8) . ?
B4 B9 1.785(8) . ?
B4 B5 1.810(8) . ?
B5 F5 1.354(6) . ?
B5 B6 1.784(8) . ?
B5 B10 1.789(8) . ?
B5 B9 1.795(7) . ?
B6 F6 1.360(5) . ?
B6 B11 1.763(7) . ?
B6 B10 1.776(8) . ?
B7 F7 1.364(6) . ?
B7 B12 1.790(9) . ?
B7 B11 1.808(7) . ?
B7 B8 1.809(8) . ?
B8 F8 1.379(6) . ?
B8 B12 1.786(8) . ?
B8 B9 1.794(8) . ?
B9 F9 1.375(6) . ?
B9 B12 1.794(8) . ?
B9 B10 1.826(7) . ?
B10 F10 1.366(6) . ?
B10 B11 1.788(8) . ?
B10 B12 1.794(7) . ?
B11 N1 1.530(6) . ?
B11 B12 1.797(8) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
B12 F12 1.366(6) . ?
O1 C2 1.421(6) . ?
O1 C3 1.436(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.482(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O2 1.423(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O2 C5 1.424(6) . ?
C5 C6 1.492(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O3 1.421(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O3 C7 1.431(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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
B6 C1 B3 115.4(4) . . ?
B6 C1 B5 62.7(3) . . ?
B3 C1 B5 115.4(4) . . ?
B6 C1 B2 63.4(3) . . ?
B3 C1 B2 62.9(3) . . ?
B5 C1 B2 115.6(4) . . ?
B6 C1 B4 115.2(4) . . ?
B3 C1 B4 62.5(3) . . ?
B5 C1 B4 63.4(3) . . ?
B2 C1 B4 115.0(4) . . ?
B6 C1 H1 117.3 . . ?
B3 C1 H1 117.5 . . ?
B5 C1 H1 117.1 . . ?
B2 C1 H1 117.2 . . ?
B4 C1 H1 117.6 . . ?
F2 B2 C1 121.0(4) . . ?
F2 B2 B11 126.3(4) . . ?
C1 B2 B11 103.3(4) . . ?
F2 B2 B7 125.6(4) . . ?
C1 B2 B7 104.2(4) . . ?
B11 B2 B7 61.0(3) . . ?
F2 B2 B3 119.9(4) . . ?
C1 B2 B3 58.2(3) . . ?
B11 B2 B3 108.2(4) . . ?
B7 B2 B3 60.1(3) . . ?
F2 B2 B6 120.7(4) . . ?
C1 B2 B6 58.0(3) . . ?
B11 B2 B6 59.0(3) . . ?
B7 B2 B6 107.8(4) . . ?
B3 B2 B6 107.1(4) . . ?
F3 B3 C1 119.9(4) . . ?
F3 B3 B4 118.1(4) . . ?
C1 B3 B4 59.2(3) . . ?
F3 B3 B8 125.5(4) . . ?
C1 B3 B8 104.3(4) . . ?
B4 B3 B8 59.3(3) . . ?
F3 B3 B7 127.1(5) . . ?
C1 B3 B7 104.4(4) . . ?
B4 B3 B7 108.5(4) . . ?
B8 B3 B7 60.9(3) . . ?
F3 B3 B2 120.7(5) . . ?
C1 B3 B2 58.9(3) . . ?
B4 B3 B2 109.0(4) . . ?
B8 B3 B2 108.5(4) . . ?
B7 B3 B2 59.7(3) . . ?
F4 B4 C1 118.3(4) . . ?
F4 B4 B8 126.5(4) . . ?
C1 B4 B8 104.4(4) . . ?
F4 B4 B3 117.2(4) . . ?
C1 B4 B3 58.3(3) . . ?
B8 B4 B3 60.3(3) . . ?
F4 B4 B9 128.5(5) . . ?
C1 B4 B9 104.4(4) . . ?
B8 B4 B9 60.8(3) . . ?
B3 B4 B9 108.9(4) . . ?
F4 B4 B5 120.8(4) . . ?
C1 B4 B5 58.2(3) . . ?
B8 B4 B5 108.2(4) . . ?
B3 B4 B5 107.7(4) . . ?
B9 B4 B5 59.9(3) . . ?
F5 B5 C1 119.8(4) . . ?
F5 B5 B6 120.8(4) . . ?
C1 B5 B6 58.4(3) . . ?
F5 B5 B10 127.3(5) . . ?
C1 B5 B10 104.1(4) . . ?
B6 B5 B10 59.6(3) . . ?
F5 B5 B9 125.7(5) . . ?
C1 B5 B9 104.2(4) . . ?
B6 B5 B9 108.5(4) . . ?
B10 B5 B9 61.3(3) . . ?
F5 B5 B4 118.7(4) . . ?
C1 B5 B4 58.5(3) . . ?
B6 B5 B4 107.6(4) . . ?
B10 B5 B4 108.2(4) . . ?
B9 B5 B4 59.4(3) . . ?
F6 B6 C1 119.7(4) . . ?
F6 B6 B11 126.2(4) . . ?
C1 B6 B11 104.6(3) . . ?
F6 B6 B10 125.8(4) . . ?
C1 B6 B10 105.2(4) . . ?
B11 B6 B10 60.7(3) . . ?
F6 B6 B5 119.1(4) . . ?
C1 B6 B5 59.0(3) . . ?
B11 B6 B5 108.8(4) . . ?
B10 B6 B5 60.3(3) . . ?
F6 B6 B2 119.5(4) . . ?
C1 B6 B2 58.7(3) . . ?
B11 B6 B2 59.9(3) . . ?
B10 B6 B2 108.8(4) . . ?
B5 B6 B2 108.7(4) . . ?
F7 B7 B2 122.3(5) . . ?
F7 B7 B3 123.9(4) . . ?
B2 B7 B3 60.3(3) . . ?
F7 B7 B12 121.1(4) . . ?
B2 B7 B12 107.4(4) . . ?
B3 B7 B12 106.6(4) . . ?
F7 B7 B11 121.0(4) . . ?
B2 B7 B11 59.4(3) . . ?
B3 B7 B11 107.1(4) . . ?
B12 B7 B11 59.9(3) . . ?
F7 B7 B8 122.5(4) . . ?
B2 B7 B8 107.8(4) . . ?
B3 B7 B8 59.3(3) . . ?
B12 B7 B8 59.5(3) . . ?
B11 B7 B8 107.4(4) . . ?
F8 B8 B4 121.2(4) . . ?
F8 B8 B3 120.9(4) . . ?
B4 B8 B3 60.3(3) . . ?
F8 B8 B12 123.1(4) . . ?
B4 B8 B12 107.8(4) . . ?
B3 B8 B12 107.2(4) . . ?
F8 B8 B9 122.0(5) . . ?
B4 B8 B9 60.2(3) . . ?
B3 B8 B9 108.5(4) . . ?
B12 B8 B9 60.2(3) . . ?
F8 B8 B7 121.2(4) . . ?
B4 B8 B7 108.4(4) . . ?
B3 B8 B7 59.8(3) . . ?
B12 B8 B7 59.7(3) . . ?
B9 B8 B7 108.6(4) . . ?
F9 B9 B4 123.3(4) . . ?
F9 B9 B8 122.5(4) . . ?
B4 B9 B8 59.0(3) . . ?
F9 B9 B12 121.9(4) . . ?
B4 B9 B12 106.4(4) . . ?
B8 B9 B12 59.7(3) . . ?
F9 B9 B5 122.4(5) . . ?
B4 B9 B5 60.7(3) . . ?
B8 B9 B5 107.5(4) . . ?
B12 B9 B5 106.4(4) . . ?
F9 B9 B10 121.1(4) . . ?
B4 B9 B10 107.6(4) . . ?
B8 B9 B10 107.4(4) . . ?
B12 B9 B10 59.4(3) . . ?
B5 B9 B10 59.2(3) . . ?
F10 B10 B6 122.9(4) . . ?
F10 B10 B11 121.4(4) . . ?
B6 B10 B11 59.3(3) . . ?
F10 B10 B5 123.0(4) . . ?
B6 B10 B5 60.0(3) . . ?
B11 B10 B5 107.5(4) . . ?
F10 B10 B12 121.6(4) . . ?
B6 B10 B12 106.9(4) . . ?
B11 B10 B12 60.2(3) . . ?
B5 B10 B12 106.6(4) . . ?
F10 B10 B9 121.8(5) . . ?
B6 B10 B9 107.5(4) . . ?
B11 B10 B9 108.0(4) . . ?
B5 B10 B9 59.5(3) . . ?
B12 B10 B9 59.4(3) . . ?
N1 B11 B6 123.8(4) . . ?
N1 B11 B2 123.1(4) . . ?
B6 B11 B2 61.2(3) . . ?
N1 B11 B10 120.6(4) . . ?
B6 B11 B10 60.0(3) . . ?
B2 B11 B10 109.3(4) . . ?
N1 B11 B12 120.0(4) . . ?
B6 B11 B12 107.3(4) . . ?
B2 B11 B12 107.1(4) . . ?
B10 B11 B12 60.1(3) . . ?
N1 B11 B7 120.5(4) . . ?
B6 B11 B7 108.4(4) . . ?
B2 B11 B7 59.5(3) . . ?
B10 B11 B7 108.6(4) . . ?
B12 B11 B7 59.5(3) . . ?
B11 N1 H1A 109.5 . . ?
B11 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
B11 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
F12 B12 B8 123.1(4) . . ?
F12 B12 B7 121.1(4) . . ?
B8 B12 B7 60.8(3) . . ?
F12 B12 B10 119.6(4) . . ?
B8 B12 B10 109.3(4) . . ?
B7 B12 B10 109.1(4) . . ?
F12 B12 B9 121.7(5) . . ?
B8 B12 B9 60.2(3) . . ?
B7 B12 B9 109.5(4) . . ?
B10 B12 B9 61.2(3) . . ?
F12 B12 B11 119.7(4) . . ?
B8 B12 B11 108.9(4) . . ?
B7 B12 B11 60.5(3) . . ?
B10 B12 B11 59.7(3) . . ?
B9 B12 B11 109.0(4) . . ?
C2 O1 C3 111.4(4) . . ?
O1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C4 108.5(5) . . ?
O1 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
O1 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
O2 C4 C3 110.8(4) . . ?
O2 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
O2 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 O2 C5 113.5(4) . . ?
O2 C5 C6 113.8(4) . . ?
O2 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
O2 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
O3 C6 C5 108.2(4) . . ?
O3 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
O3 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C6 O3 C7 113.5(4) . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.115

_shelxl_version_number           2013-4

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

data_12H3NHCB11F10
_database_code_depnum_ccdc_archive 'CCDC 1401860'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;


#=================================================================
#DATA 1
#================================================================= 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C H4 B11 F10 N, H2 O'
_chemical_formula_sum            'C H6 B11 F10 N O'
_chemical_formula_weight         356.98

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

_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'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, z+1/2'

_cell_length_a                   12.356(4)
_cell_length_b                   20.211(6)
_cell_length_c                   9.735(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2431.2(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2078
_cell_measurement_theta_min      3.2965
_cell_measurement_theta_max      21.3185

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.216
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2012/1 (Bruker 2012)'

_exptl_special_details           
;
  The crystal was immersed in a film of perfluoropolyether oil, mounted
on a polyimide microloop (MicroMounts of MiTeGen) and transferred to
stream of cold nitrogen (Oxford Cryostream 700). 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19274
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.932
_diffrn_reflns_theta_max         25.997
_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             2384
_reflns_number_gt                1862
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_max     0.998
_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-2013 (Sheldrick, 2013)'
_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)+(0.0031P)²+4.6387P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2384
_refine_ls_number_parameters     227
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.310
_refine_ls_restrained_S_all      1.309
_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
C1 C 0.4001(5) 0.3847(3) 0.3875(7) 0.0135(13) Uani 1 1 d . . . . .
H1 H 0.480(4) 0.3951(6) 0.436(3) 0.016 Uiso 1 1 calc R U . . .
B2 B 0.2860(5) 0.3913(3) 0.4904(8) 0.0133(16) Uani 1 1 d . . . . .
F2 F 0.2969(3) 0.40656(16) 0.6260(4) 0.0181(8) Uani 1 1 d . . . . .
B3 B 0.3169(6) 0.4516(3) 0.3579(8) 0.0140(17) Uani 1 1 d . . . . .
F3 F 0.3505(3) 0.51293(16) 0.3921(4) 0.0208(9) Uani 1 1 d . . . . .
B4 B 0.3829(6) 0.4086(4) 0.2188(7) 0.0157(17) Uani 1 1 d . . . . .
F4 F 0.4683(3) 0.43578(17) 0.1497(4) 0.0245(9) Uani 1 1 d . . . . .
B5 B 0.3939(6) 0.3229(4) 0.2666(8) 0.0160(17) Uani 1 1 d . . . . .
F5 F 0.4865(3) 0.28813(17) 0.2373(4) 0.0215(9) Uani 1 1 d . . . . .
B6 B 0.3344(6) 0.3117(3) 0.4314(7) 0.0125(17) Uani 1 1 d . . . . .
F6 F 0.3844(3) 0.26797(16) 0.5170(4) 0.0192(9) Uani 1 1 d . . . . .
B7 B 0.1848(5) 0.4183(3) 0.3754(8) 0.0110(15) Uani 1 1 d . . . . .
F7 F 0.0969(3) 0.45618(16) 0.4095(4) 0.0175(8) Uani 1 1 d . . . . .
B8 B 0.2436(6) 0.4292(3) 0.2057(8) 0.0112(16) Uani 1 1 d . . . . .
F8 F 0.1983(3) 0.47240(16) 0.1175(4) 0.0209(9) Uani 1 1 d . . . . .
B9 B 0.2937(5) 0.3487(3) 0.1479(8) 0.0134(16) Uani 1 1 d . . . . .
F9 F 0.2950(3) 0.33316(17) 0.0117(4) 0.0173(8) Uani 1 1 d . . . . .
B10 B 0.2614(5) 0.2884(3) 0.2815(7) 0.0101(15) Uani 1 1 d . . . . .
F10 F 0.2428(3) 0.22321(16) 0.2511(3) 0.0154(9) Uani 1 1 d . . . . .
B11 B 0.1941(6) 0.3318(4) 0.4217(7) 0.0122(16) Uani 1 1 d . . . . .
F11 F 0.1146(3) 0.30308(16) 0.4994(4) 0.0150(8) Uani 1 1 d . . . . .
B12 B 0.1715(5) 0.3552(3) 0.2470(8) 0.0122(16) Uani 1 1 d . . . . .
N1 N 0.0607(4) 0.3454(2) 0.1776(5) 0.0133(12) Uani 1 1 d . . . . .
H1A H 0.0469(15) 0.3034(14) 0.171(4) 0.016 Uiso 1 1 calc R U . . .
H1B H 0.0617(10) 0.3631(17) 0.096(3) 0.016 Uiso 1 1 calc R U . . .
H1C H 0.0107(17) 0.3643(17) 0.227(3) 0.016 Uiso 1 1 calc R U . . .
O1 O 0.1029(3) 0.6111(2) 0.3715(5) 0.0262(12) Uani 1 1 d D . . . .
H2 H 0.165(2) 0.6200(19) 0.336(6) 0.031 Uiso 1 1 d D U . . .
H3 H 0.094(3) 0.5688(5) 0.373(7) 0.031 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 B5 1.718(9) . ?
C1 B3 1.723(9) . ?
C1 B4 1.725(9) . ?
C1 B2 1.735(9) . ?
C1 B6 1.739(9) . ?
C1 H1 1.11(6) . ?
B2 F2 1.362(8) . ?
B2 B7 1.766(10) . ?
B2 B11 1.784(10) . ?
B2 B6 1.810(10) . ?
B2 B3 1.816(10) . ?
B3 F3 1.348(8) . ?
B3 B7 1.774(10) . ?
B3 B8 1.794(10) . ?
B3 B4 1.805(10) . ?
B4 F4 1.367(8) . ?
B4 B8 1.775(10) . ?
B4 B9 1.777(10) . ?
B4 B5 1.797(10) . ?
B5 F5 1.373(8) . ?
B5 B9 1.772(10) . ?
B5 B6 1.779(11) . ?
B5 B10 1.785(10) . ?
B6 F6 1.363(8) . ?
B6 B10 1.778(10) . ?
B6 B11 1.783(10) . ?
B7 F7 1.369(7) . ?
B7 B12 1.794(10) . ?
B7 B11 1.809(9) . ?
B7 B8 1.818(10) . ?
B8 F8 1.347(8) . ?
B8 B12 1.786(10) . ?
B8 B9 1.830(10) . ?
B9 F9 1.363(8) . ?
B9 B12 1.796(10) . ?
B9 B10 1.826(10) . ?
B10 F10 1.371(7) . ?
B10 B12 1.780(9) . ?
B10 B11 1.823(10) . ?
B11 F11 1.369(8) . ?
B11 B12 1.787(10) . ?
B12 N1 1.540(8) . ?
N1 H1A 0.87(3) . ?
N1 H1B 0.87(3) . ?
N1 H1C 0.87(3) . ?
O1 H2 0.859(7) . ?
O1 H3 0.862(7) . ?

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
B5 C1 B3 115.4(5) . . ?
B5 C1 B4 62.9(4) . . ?
B3 C1 B4 63.1(4) . . ?
B5 C1 B2 114.5(5) . . ?
B3 C1 B2 63.4(4) . . ?
B4 C1 B2 115.4(5) . . ?
B5 C1 B6 62.0(4) . . ?
B3 C1 B6 115.4(5) . . ?
B4 C1 B6 114.4(5) . . ?
B2 C1 B6 62.8(4) . . ?
B5 C1 H1 117.9 . . ?
B3 C1 H1 116.8 . . ?
B4 C1 H1 117.5 . . ?
B2 C1 H1 117.4 . . ?
B6 C1 H1 118.0 . . ?
F2 B2 C1 119.8(5) . . ?
F2 B2 B7 127.9(5) . . ?
C1 B2 B7 103.5(5) . . ?
F2 B2 B11 125.4(5) . . ?
C1 B2 B11 104.4(5) . . ?
B7 B2 B11 61.3(4) . . ?
F2 B2 B6 118.4(5) . . ?
C1 B2 B6 58.7(4) . . ?
B7 B2 B6 107.9(5) . . ?
B11 B2 B6 59.5(4) . . ?
F2 B2 B3 121.1(5) . . ?
C1 B2 B3 58.0(4) . . ?
B7 B2 B3 59.4(4) . . ?
B11 B2 B3 108.6(5) . . ?
B6 B2 B3 107.6(5) . . ?
F3 B3 C1 119.7(5) . . ?
F3 B3 B7 127.5(6) . . ?
C1 B3 B7 103.6(5) . . ?
F3 B3 B8 126.3(6) . . ?
C1 B3 B8 103.9(5) . . ?
B7 B3 B8 61.3(4) . . ?
F3 B3 B4 119.3(6) . . ?
C1 B3 B4 58.5(4) . . ?
B7 B3 B4 107.8(5) . . ?
B8 B3 B4 59.1(4) . . ?
F3 B3 B2 120.4(6) . . ?
C1 B3 B2 58.6(4) . . ?
B7 B3 B2 58.9(4) . . ?
B8 B3 B2 108.1(5) . . ?
B4 B3 B2 107.7(5) . . ?
F4 B4 C1 119.1(6) . . ?
F4 B4 B8 128.2(6) . . ?
C1 B4 B8 104.7(5) . . ?
F4 B4 B9 124.2(6) . . ?
C1 B4 B9 104.8(5) . . ?
B8 B4 B9 62.0(4) . . ?
F4 B4 B5 117.2(6) . . ?
C1 B4 B5 58.3(4) . . ?
B8 B4 B5 108.5(5) . . ?
B9 B4 B5 59.4(4) . . ?
F4 B4 B3 121.6(6) . . ?
C1 B4 B3 58.4(4) . . ?
B8 B4 B3 60.2(4) . . ?
B9 B4 B3 109.9(5) . . ?
B5 B4 B3 107.7(5) . . ?
F5 B5 C1 118.5(6) . . ?
F5 B5 B9 126.7(6) . . ?
C1 B5 B9 105.4(5) . . ?
F5 B5 B6 117.8(6) . . ?
C1 B5 B6 59.6(4) . . ?
B9 B5 B6 109.7(5) . . ?
F5 B5 B10 125.5(6) . . ?
C1 B5 B10 105.6(5) . . ?
B9 B5 B10 61.8(4) . . ?
B6 B5 B10 59.9(4) . . ?
F5 B5 B4 120.2(6) . . ?
C1 B5 B4 58.7(4) . . ?
B9 B5 B4 59.7(4) . . ?
B6 B5 B4 109.0(5) . . ?
B10 B5 B4 109.2(5) . . ?
F6 B6 C1 119.3(5) . . ?
F6 B6 B10 124.1(5) . . ?
C1 B6 B10 105.0(5) . . ?
F6 B6 B5 116.6(5) . . ?
C1 B6 B5 58.4(4) . . ?
B10 B6 B5 60.2(4) . . ?
F6 B6 B11 128.4(6) . . ?
C1 B6 B11 104.3(5) . . ?
B10 B6 B11 61.6(4) . . ?
B5 B6 B11 108.9(5) . . ?
F6 B6 B2 122.1(6) . . ?
C1 B6 B2 58.5(4) . . ?
B10 B6 B2 109.1(5) . . ?
B5 B6 B2 108.0(5) . . ?
B11 B6 B2 59.5(4) . . ?
F7 B7 B2 125.5(6) . . ?
F7 B7 B3 122.7(5) . . ?
B2 B7 B3 61.7(4) . . ?
F7 B7 B12 119.7(5) . . ?
B2 B7 B12 106.7(5) . . ?
B3 B7 B12 106.7(5) . . ?
F7 B7 B11 122.0(5) . . ?
B2 B7 B11 59.9(4) . . ?
B3 B7 B11 109.4(5) . . ?
B12 B7 B11 59.5(4) . . ?
F7 B7 B8 118.1(5) . . ?
B2 B7 B8 109.3(5) . . ?
B3 B7 B8 59.9(4) . . ?
B12 B7 B8 59.3(4) . . ?
B11 B7 B8 108.5(5) . . ?
F8 B8 B4 127.0(6) . . ?
F8 B8 B12 118.6(5) . . ?
B4 B8 B12 105.7(5) . . ?
F8 B8 B3 124.9(6) . . ?
B4 B8 B3 60.7(4) . . ?
B12 B8 B3 106.1(5) . . ?
F8 B8 B7 119.4(5) . . ?
B4 B8 B7 107.1(5) . . ?
B12 B8 B7 59.7(4) . . ?
B3 B8 B7 58.8(4) . . ?
F8 B8 B9 121.4(6) . . ?
B4 B8 B9 59.1(4) . . ?
B12 B8 B9 59.5(4) . . ?
B3 B8 B9 108.0(5) . . ?
B7 B8 B9 107.9(5) . . ?
F9 B9 B5 124.0(5) . . ?
F9 B9 B4 121.8(5) . . ?
B5 B9 B4 60.8(4) . . ?
F9 B9 B12 123.4(5) . . ?
B5 B9 B12 105.0(5) . . ?
B4 B9 B12 105.2(5) . . ?
F9 B9 B10 122.9(5) . . ?
B5 B9 B10 59.5(4) . . ?
B4 B9 B10 108.2(5) . . ?
B12 B9 B10 58.9(4) . . ?
F9 B9 B8 120.5(5) . . ?
B5 B9 B8 107.2(5) . . ?
B4 B9 B8 58.9(4) . . ?
B12 B9 B8 59.0(4) . . ?
B10 B9 B8 107.5(5) . . ?
F10 B10 B6 121.1(5) . . ?
F10 B10 B12 125.7(5) . . ?
B6 B10 B12 105.7(5) . . ?
F10 B10 B5 120.8(5) . . ?
B6 B10 B5 59.9(4) . . ?
B12 B10 B5 105.1(5) . . ?
F10 B10 B11 123.2(5) . . ?
B6 B10 B11 59.3(4) . . ?
B12 B10 B11 59.5(4) . . ?
B5 B10 B11 106.9(5) . . ?
F10 B10 B9 121.6(5) . . ?
B6 B10 B9 107.3(5) . . ?
B12 B10 B9 59.7(4) . . ?
B5 B10 B9 58.8(4) . . ?
B11 B10 B9 108.2(5) . . ?
F11 B11 B6 124.8(5) . . ?
F11 B11 B2 122.4(5) . . ?
B6 B11 B2 61.0(4) . . ?
F11 B11 B12 121.8(5) . . ?
B6 B11 B12 105.2(5) . . ?
B2 B11 B12 106.1(5) . . ?
F11 B11 B7 120.2(5) . . ?
B6 B11 B7 107.2(5) . . ?
B2 B11 B7 58.9(4) . . ?
B12 B11 B7 59.8(4) . . ?
F11 B11 B10 122.5(5) . . ?
B6 B11 B10 59.1(4) . . ?
B2 B11 B10 108.3(5) . . ?
B12 B11 B10 59.1(4) . . ?
B7 B11 B10 107.9(5) . . ?
N1 B12 B10 122.7(5) . . ?
N1 B12 B11 121.5(5) . . ?
B10 B12 B11 61.5(4) . . ?
N1 B12 B8 116.9(5) . . ?
B10 B12 B8 111.5(5) . . ?
B11 B12 B8 110.9(5) . . ?
N1 B12 B7 118.5(5) . . ?
B10 B12 B7 110.5(5) . . ?
B11 B12 B7 60.7(4) . . ?
B8 B12 B7 61.0(4) . . ?
N1 B12 B9 120.2(5) . . ?
B10 B12 B9 61.4(4) . . ?
B11 B12 B9 111.1(5) . . ?
B8 B12 B9 61.4(4) . . ?
B7 B12 B9 110.5(5) . . ?
B12 N1 H1A 109.5 . . ?
B12 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
B12 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
H2 O1 H3 108.9(10) . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-4

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

data_7H3N12FCB11H10
_database_code_depnum_ccdc_archive 'CCDC 1401861'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;


#=================================================================
#DATA 1
#================================================================= 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H19 B11 F N O'
_chemical_formula_weight         235.11

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.8577(8)
_cell_length_b                   10.3265(8)
_cell_length_c                   13.5715(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.499(2)
_cell_angle_gamma                90
_cell_volume                     1372.64(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7036
_cell_measurement_theta_min      2.4845
_cell_measurement_theta_max      26.067

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2012/1 (Bruker 2012)'

_exptl_special_details           
;
 The crystal was immersed in a film of perfluoropolyether oil, mounted
on a polyimide microloop (MicroMounts of MiTeGen) and transferred to
stream of cold nitrogen (Oxford Cryostream 700).
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  helios
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14304
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_max         26.087
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2726
_reflns_number_gt                2385
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. 8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0815P)²+0.2877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2726
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
C1 C 0.91410(13) 0.27934(12) 0.26834(9) 0.0203(3) Uani 1 1 d . . . . .
H1 H 1.0093(17) 0.2987(15) 0.2742(11) 0.024(4) Uiso 1 1 d . . . . .
B2 B 0.83112(14) 0.30846(13) 0.36973(10) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.8843(17) 0.3524(16) 0.4366(13) 0.032(4) Uiso 1 1 d . . . . .
B3 B 0.79792(13) 0.40206(13) 0.25867(10) 0.0165(3) Uani 1 1 d . . . . .
H3 H 0.8321(16) 0.5012(16) 0.2594(11) 0.029(4) Uiso 1 1 d . . . . .
B4 B 0.81765(13) 0.29977(13) 0.15625(10) 0.0175(3) Uani 1 1 d . . . . .
H4 H 0.8682(17) 0.3383(16) 0.0950(12) 0.033(4) Uiso 1 1 d . . . . .
B5 B 0.86243(14) 0.14235(14) 0.20339(10) 0.0201(3) Uani 1 1 d . . . . .
H5 H 0.9412(14) 0.0872(14) 0.1728(11) 0.021(4) Uiso 1 1 d . . . . .
B6 B 0.87063(15) 0.14775(14) 0.33551(11) 0.0213(3) Uani 1 1 d . . . . .
H6 H 0.9512(17) 0.0959(16) 0.3811(13) 0.035(4) Uiso 1 1 d . . . . .
B7 B 0.66241(13) 0.34084(12) 0.31879(9) 0.0138(3) Uani 1 1 d . . . . .
N1 N 0.56904(11) 0.43229(10) 0.37103(8) 0.0164(2) Uani 1 1 d . . . . .
H1A H 0.6121(16) 0.4823(16) 0.4184(13) 0.030(4) Uiso 1 1 d . . . . .
H1B H 0.5262(19) 0.4854(18) 0.3264(14) 0.040(5) Uiso 1 1 d . . . . .
H1C H 0.5014(16) 0.3948(15) 0.4014(12) 0.026(4) Uiso 1 1 d . . . . .
B8 B 0.65219(13) 0.33694(12) 0.18687(9) 0.0140(3) Uani 1 1 d . . . . .
H8 H 0.5801(15) 0.3969(14) 0.1415(11) 0.021(3) Uiso 1 1 d . . . . .
B9 B 0.69319(13) 0.17614(12) 0.15259(10) 0.0156(3) Uani 1 1 d . . . . .
H9 H 0.6518(15) 0.1348(15) 0.0836(12) 0.025(4) Uiso 1 1 d . . . . .
B10 B 0.72544(14) 0.08177(13) 0.26369(10) 0.0181(3) Uani 1 1 d . . . . .
H10 H 0.6997(14) -0.0260(13) 0.2667(10) 0.015(3) Uiso 1 1 d . . . . .
B11 B 0.70536(14) 0.18451(12) 0.36727(10) 0.0168(3) Uani 1 1 d . . . . .
H11 H 0.6622(13) 0.1467(12) 0.4368(10) 0.010(3) Uiso 1 1 d . . . . .
B12 B 0.59564(13) 0.20219(12) 0.25333(9) 0.0140(3) Uani 1 1 d . . . . .
F1 F 0.45812(7) 0.17112(7) 0.24734(5) 0.0201(2) Uani 1 1 d . . . . .
O1 O 0.35415(9) 0.35985(8) 0.48968(7) 0.0231(2) Uani 1 1 d . . . . .
C2 C 0.28651(12) 0.26454(11) 0.50588(9) 0.0179(3) Uani 1 1 d . . . . .
C3 C 0.30782(16) 0.13793(13) 0.45799(12) 0.0329(4) Uani 1 1 d . . . . .
H3A H 0.2247 0.1117 0.4194 0.049 Uiso 1 1 calc R U . . .
H3B H 0.3336 0.0741 0.5081 0.049 Uiso 1 1 calc R U . . .
H3C H 0.3789 0.1462 0.4156 0.049 Uiso 1 1 calc R U . . .
C4 C 0.18010(14) 0.27015(13) 0.57585(11) 0.0282(3) Uani 1 1 d . . . . .
H4A H 0.1628 0.3588 0.5916 0.042 Uiso 1 1 calc R U . . .
H4B H 0.2117 0.2241 0.6355 0.042 Uiso 1 1 calc R U . . .
H4C H 0.0974 0.2311 0.5454 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 B3 1.7032(18) . ?
C1 B2 1.7052(18) . ?
C1 B4 1.7132(18) . ?
C1 B5 1.7134(19) . ?
C1 B6 1.7174(19) . ?
C1 H1 0.954(16) . ?
B2 B7 1.7594(19) . ?
B2 B6 1.778(2) . ?
B2 B11 1.7795(19) . ?
B2 B3 1.7894(19) . ?
B2 H2 1.094(17) . ?
B3 B7 1.7597(18) . ?
B3 B4 1.7739(18) . ?
B3 B8 1.7745(18) . ?
B3 H3 1.078(17) . ?
B4 B9 1.7674(18) . ?
B4 B8 1.7703(18) . ?
B4 B5 1.7840(19) . ?
B4 H4 1.091(17) . ?
B5 B9 1.7664(19) . ?
B5 B10 1.7705(19) . ?
B5 B6 1.787(2) . ?
B5 H5 1.083(15) . ?
B6 B11 1.7729(19) . ?
B6 B10 1.774(2) . ?
B6 H6 1.091(17) . ?
B7 N1 1.5458(15) . ?
B7 B12 1.7720(18) . ?
B7 B11 1.7763(17) . ?
B7 B8 1.7821(17) . ?
N1 H1A 0.894(18) . ?
N1 H1B 0.89(2) . ?
N1 H1C 0.909(17) . ?
B8 B12 1.7816(17) . ?
B8 B9 1.7831(18) . ?
B8 H8 1.081(15) . ?
B9 B12 1.7787(17) . ?
B9 B10 1.7933(19) . ?
B9 H9 1.067(16) . ?
B10 B12 1.7784(18) . ?
B10 B11 1.7899(18) . ?
B10 H10 1.143(14) . ?
B11 B12 1.7932(18) . ?
B11 H11 1.147(13) . ?
B12 F1 1.3865(15) . ?
O1 C2 1.2227(15) . ?
C2 C3 1.4855(17) . ?
C2 C4 1.4936(17) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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
B3 C1 B2 63.33(8) . . ?
B3 C1 B4 62.56(8) . . ?
B2 C1 B4 115.22(9) . . ?
B3 C1 B5 114.62(10) . . ?
B2 C1 B5 114.77(10) . . ?
B4 C1 B5 62.75(8) . . ?
B3 C1 B6 115.07(9) . . ?
B2 C1 B6 62.61(8) . . ?
B4 C1 B6 114.96(10) . . ?
B5 C1 B6 62.76(8) . . ?
B3 C1 H1 119.8(9) . . ?
B2 C1 H1 116.9(9) . . ?
B4 C1 H1 119.3(9) . . ?
B5 C1 H1 116.6(9) . . ?
B6 C1 H1 115.1(9) . . ?
C1 B2 B7 103.58(9) . . ?
C1 B2 B6 59.03(8) . . ?
B7 B2 B6 107.46(9) . . ?
C1 B2 B11 104.76(9) . . ?
B7 B2 B11 60.25(7) . . ?
B6 B2 B11 59.77(8) . . ?
C1 B2 B3 58.28(7) . . ?
B7 B2 B3 59.45(7) . . ?
B6 B2 B3 107.98(9) . . ?
B11 B2 B3 108.19(9) . . ?
C1 B2 H2 120.9(9) . . ?
B7 B2 H2 126.2(9) . . ?
B6 B2 H2 120.4(9) . . ?
B11 B2 H2 125.5(9) . . ?
B3 B2 H2 120.0(9) . . ?
C1 B3 B7 103.65(9) . . ?
C1 B3 B4 59.00(7) . . ?
B7 B3 B4 107.80(9) . . ?
C1 B3 B8 104.82(9) . . ?
B7 B3 B8 60.56(7) . . ?
B4 B3 B8 59.85(7) . . ?
C1 B3 B2 58.39(7) . . ?
B7 B3 B2 59.43(7) . . ?
B4 B3 B2 108.21(9) . . ?
B8 B3 B2 108.50(9) . . ?
C1 B3 H3 120.0(8) . . ?
B7 B3 H3 126.1(8) . . ?
B4 B3 H3 120.8(8) . . ?
B8 B3 H3 126.7(8) . . ?
B2 B3 H3 118.6(8) . . ?
C1 B4 B9 104.46(9) . . ?
C1 B4 B8 104.58(9) . . ?
B9 B4 B8 60.54(7) . . ?
C1 B4 B3 58.44(7) . . ?
B9 B4 B3 108.35(9) . . ?
B8 B4 B3 60.09(7) . . ?
C1 B4 B5 58.63(7) . . ?
B9 B4 B5 59.65(7) . . ?
B8 B4 B5 108.09(9) . . ?
B3 B4 B5 107.83(9) . . ?
C1 B4 H4 117.8(9) . . ?
B9 B4 H4 128.1(9) . . ?
B8 B4 H4 127.7(9) . . ?
B3 B4 H4 118.7(9) . . ?
B5 B4 H4 119.3(9) . . ?
C1 B5 B9 104.50(9) . . ?
C1 B5 B10 104.58(9) . . ?
B9 B5 B10 60.93(8) . . ?
C1 B5 B4 58.62(7) . . ?
B9 B5 B4 59.71(7) . . ?
B10 B5 B4 108.48(9) . . ?
C1 B5 B6 58.73(8) . . ?
B9 B5 B6 108.60(9) . . ?
B10 B5 B6 59.83(8) . . ?
B4 B5 B6 108.22(9) . . ?
C1 B5 H5 116.5(8) . . ?
B9 B5 H5 129.9(8) . . ?
B10 B5 H5 127.5(8) . . ?
B4 B5 H5 120.0(8) . . ?
B6 B5 H5 116.6(8) . . ?
C1 B6 B11 104.54(9) . . ?
C1 B6 B10 104.27(9) . . ?
B11 B6 B10 60.62(8) . . ?
C1 B6 B2 58.36(7) . . ?
B11 B6 B2 60.15(8) . . ?
B10 B6 B2 108.36(9) . . ?
C1 B6 B5 58.51(8) . . ?
B11 B6 B5 108.19(9) . . ?
B10 B6 B5 59.64(8) . . ?
B2 B6 B5 107.75(9) . . ?
C1 B6 H6 118.7(9) . . ?
B11 B6 H6 126.7(9) . . ?
B10 B6 H6 127.9(9) . . ?
B2 B6 H6 118.5(9) . . ?
B5 B6 H6 120.1(9) . . ?
N1 B7 B2 121.42(10) . . ?
N1 B7 B3 121.05(9) . . ?
B2 B7 B3 61.12(8) . . ?
N1 B7 B12 121.13(10) . . ?
B2 B7 B12 108.93(9) . . ?
B3 B7 B12 108.44(9) . . ?
N1 B7 B11 120.98(10) . . ?
B2 B7 B11 60.43(7) . . ?
B3 B7 B11 109.67(9) . . ?
B12 B7 B11 60.71(7) . . ?
N1 B7 B8 120.38(9) . . ?
B2 B7 B8 109.51(9) . . ?
B3 B7 B8 60.13(7) . . ?
B12 B7 B8 60.17(7) . . ?
B11 B7 B8 109.61(8) . . ?
B7 N1 H1A 115.1(10) . . ?
B7 N1 H1B 109.0(12) . . ?
H1A N1 H1B 106.5(16) . . ?
B7 N1 H1C 117.0(10) . . ?
H1A N1 H1C 103.4(14) . . ?
H1B N1 H1C 104.8(15) . . ?
B4 B8 B3 60.06(7) . . ?
B4 B8 B12 107.39(9) . . ?
B3 B8 B12 107.35(9) . . ?
B4 B8 B7 106.97(9) . . ?
B3 B8 B7 59.31(7) . . ?
B12 B8 B7 59.63(7) . . ?
B4 B8 B9 59.65(7) . . ?
B3 B8 B9 107.63(9) . . ?
B12 B8 B9 59.86(7) . . ?
B7 B8 B9 107.13(9) . . ?
B4 B8 H8 123.6(8) . . ?
B3 B8 H8 122.3(8) . . ?
B12 B8 H8 120.9(8) . . ?
B7 B8 H8 121.2(8) . . ?
B9 B8 H8 122.6(8) . . ?
B5 B9 B4 60.64(8) . . ?
B5 B9 B12 107.38(9) . . ?
B4 B9 B12 107.64(9) . . ?
B5 B9 B8 108.30(9) . . ?
B4 B9 B8 59.81(7) . . ?
B12 B9 B8 60.03(7) . . ?
B5 B9 B10 59.65(8) . . ?
B4 B9 B10 108.21(9) . . ?
B12 B9 B10 59.72(7) . . ?
B8 B9 B10 108.09(9) . . ?
B5 B9 H9 120.9(8) . . ?
B4 B9 H9 120.6(8) . . ?
B12 B9 H9 123.2(8) . . ?
B8 B9 H9 121.8(8) . . ?
B10 B9 H9 122.2(8) . . ?
B5 B10 B6 60.53(8) . . ?
B5 B10 B12 107.21(9) . . ?
B6 B10 B12 107.66(9) . . ?
B5 B10 B11 108.15(9) . . ?
B6 B10 B11 59.66(8) . . ?
B12 B10 B11 60.34(7) . . ?
B5 B10 B9 59.42(7) . . ?
B6 B10 B9 107.97(9) . . ?
B12 B10 B9 59.74(7) . . ?
B11 B10 B9 108.26(9) . . ?
B5 B10 H10 123.0(7) . . ?
B6 B10 H10 121.5(7) . . ?
B12 B10 H10 121.5(7) . . ?
B11 B10 H10 120.3(7) . . ?
B9 B10 H10 122.7(7) . . ?
B6 B11 B7 106.95(9) . . ?
B6 B11 B2 60.08(8) . . ?
B7 B11 B2 59.31(7) . . ?
B6 B11 B10 59.72(8) . . ?
B7 B11 B10 106.90(9) . . ?
B2 B11 B10 107.60(9) . . ?
B6 B11 B12 107.06(9) . . ?
B7 B11 B12 59.52(7) . . ?
B2 B11 B12 107.09(9) . . ?
B10 B11 B12 59.51(7) . . ?
B6 B11 H11 124.3(6) . . ?
B7 B11 H11 121.3(6) . . ?
B2 B11 H11 123.5(6) . . ?
B10 B11 H11 121.9(6) . . ?
B12 B11 H11 120.0(6) . . ?
F1 B12 B7 121.44(9) . . ?
F1 B12 B10 122.19(9) . . ?
B7 B12 B10 107.59(9) . . ?
F1 B12 B9 122.00(10) . . ?
B7 B12 B9 107.76(9) . . ?
B10 B12 B9 60.55(7) . . ?
F1 B12 B8 120.72(9) . . ?
B7 B12 B8 60.20(7) . . ?
B10 B12 B8 108.82(9) . . ?
B9 B12 B8 60.11(7) . . ?
F1 B12 B11 121.15(9) . . ?
B7 B12 B11 59.76(7) . . ?
B10 B12 B11 60.15(7) . . ?
B9 B12 B11 108.76(9) . . ?
B8 B12 B11 108.86(9) . . ?
O1 C2 C3 121.52(11) . . ?
O1 C2 C4 121.31(11) . . ?
C3 C2 C4 117.17(11) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

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

data_Et4N12H2NHCB11F10
_database_code_depnum_ccdc_archive 'CCDC 1401862'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;


#=================================================================
#DATA 1
#================================================================= 


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C H3 B11 F10 N, C8 H20 N'
_chemical_formula_sum            'C9 H23 B11 F10 N2'
_chemical_formula_weight         468.20

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.3754(10)
_cell_length_b                   11.0807(8)
_cell_length_c                   13.7559(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.726(3)
_cell_angle_gamma                90
_cell_volume                     1988.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1560
_cell_measurement_theta_min      2.4045
_cell_measurement_theta_max      26.0535

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
  The crystal was immersed in a film of perfluoropolyether oil, mounted
on a polyimide microloop (MicroMounts of MiTeGen) and transferred to
stream of cold nitrogen (Oxford Cryostream 700).
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25500
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.923
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4066
_reflns_number_gt                3225
_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.4087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4066
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C1 C 0.34718(12) 0.36282(15) 0.63121(12) 0.0142(4) Uani 1 1 d . . . . .
H1 H 0.34676(12) 0.4529(17) 0.63665(16) 0.017 Uiso 1 1 calc R U . . .
B2 B 0.39758(14) 0.30152(17) 0.53774(14) 0.0141(4) Uani 1 1 d . . . . .
F2 F 0.43481(7) 0.37414(8) 0.47450(7) 0.0178(2) Uani 1 1 d . . . . .
B3 B 0.26199(14) 0.29968(17) 0.53256(14) 0.0143(4) Uani 1 1 d . . . . .
F3 F 0.19929(7) 0.37255(9) 0.46666(7) 0.0188(2) Uani 1 1 d . . . . .
B4 B 0.24477(14) 0.28566(17) 0.65742(14) 0.0142(4) Uani 1 1 d . . . . .
F4 F 0.16795(7) 0.34636(9) 0.68654(7) 0.0184(2) Uani 1 1 d . . . . .
B5 B 0.36954(15) 0.28184(18) 0.74055(14) 0.0154(4) Uani 1 1 d . . . . .
F5 F 0.38321(8) 0.34294(9) 0.82805(7) 0.0206(2) Uani 1 1 d . . . . .
B6 B 0.46397(14) 0.29165(17) 0.66671(14) 0.0146(4) Uani 1 1 d . . . . .
F6 F 0.55054(7) 0.35802(9) 0.69882(7) 0.0191(2) Uani 1 1 d . . . . .
B7 B 0.32538(15) 0.16682(17) 0.50433(14) 0.0138(4) Uani 1 1 d . . . . .
F7 F 0.30925(7) 0.12235(9) 0.40905(7) 0.0181(2) Uani 1 1 d . . . . .
B8 B 0.23037(14) 0.15750(17) 0.57854(14) 0.0145(4) Uani 1 1 d . . . . .
F8 F 0.13653(7) 0.10386(9) 0.54407(8) 0.0220(2) Uani 1 1 d . . . . .
B9 B 0.29756(15) 0.14646(17) 0.70814(14) 0.0147(4) Uani 1 1 d . . . . .
F9 F 0.25673(7) 0.08662(9) 0.77776(7) 0.0192(2) Uani 1 1 d . . . . .
B10 B 0.43396(14) 0.14937(17) 0.71382(14) 0.0148(4) Uani 1 1 d . . . . .
F10 F 0.50230(7) 0.08668(9) 0.78479(7) 0.0192(2) Uani 1 1 d . . . . .
B11 B 0.45072(14) 0.16185(17) 0.58800(14) 0.0136(4) Uani 1 1 d . . . . .
F11 F 0.53376(7) 0.11125(8) 0.55983(7) 0.0183(2) Uani 1 1 d . . . . .
B12 B 0.34758(14) 0.07054(17) 0.61306(14) 0.0135(4) Uani 1 1 d . . . . .
N1 N 0.34641(12) -0.05913(13) 0.60227(11) 0.0141(3) Uani 1 1 d . . . . .
H1B H 0.3893(15) -0.0840(18) 0.5820(14) 0.017 Uiso 1 1 d . U . . .
H1A H 0.3389(15) -0.0921(18) 0.6455(15) 0.017 Uiso 1 1 d . U . . .
N2 N 0.35606(10) 0.25642(12) 0.13602(10) 0.0125(3) Uani 1 1 d . . . . .
C2 C 0.29816(13) 0.37240(15) 0.14451(13) 0.0161(4) Uani 1 1 d . . . . .
H2A H 0.3461 0.4411 0.1477 0.019 Uiso 1 1 calc R U . . .
H2B H 0.2437 0.3821 0.0833 0.019 Uiso 1 1 calc R U . . .
C3 C 0.24950(14) 0.37869(16) 0.23400(13) 0.0195(4) Uani 1 1 d . . . . .
H3A H 0.2075 0.4518 0.2298 0.029 Uiso 1 1 calc R U . . .
H3B H 0.3033 0.3808 0.2952 0.029 Uiso 1 1 calc R U . . .
H3C H 0.2062 0.3075 0.2348 0.029 Uiso 1 1 calc R U . . .
C4 C 0.40236(14) 0.27019(16) 0.04503(13) 0.0188(4) Uani 1 1 d . . . . .
H4A H 0.4554 0.3340 0.0588 0.023 Uiso 1 1 calc R U . . .
H4B H 0.3480 0.2977 -0.0117 0.023 Uiso 1 1 calc R U . . .
C5 C 0.45051(14) 0.15578(17) 0.01423(13) 0.0233(4) Uani 1 1 d . . . . .
H5A H 0.3965 0.0971 -0.0122 0.035 Uiso 1 1 calc R U . . .
H5B H 0.4977 0.1213 0.0723 0.035 Uiso 1 1 calc R U . . .
H5C H 0.4883 0.1753 -0.0372 0.035 Uiso 1 1 calc R U . . .
C6 C 0.28529(13) 0.14832(15) 0.12474(13) 0.0170(4) Uani 1 1 d . . . . .
H6A H 0.2552 0.1434 0.1842 0.020 Uiso 1 1 calc R U . . .
H6B H 0.3265 0.0744 0.1232 0.020 Uiso 1 1 calc R U . . .
C7 C 0.19860(13) 0.15009(16) 0.03228(13) 0.0201(4) Uani 1 1 d . . . . .
H7A H 0.2273 0.1495 -0.0274 0.030 Uiso 1 1 calc R U . . .
H7B H 0.1574 0.2232 0.0326 0.030 Uiso 1 1 calc R U . . .
H7C H 0.1553 0.0788 0.0321 0.030 Uiso 1 1 calc R U . . .
C8 C 0.43915(13) 0.23422(16) 0.22966(12) 0.0174(4) Uani 1 1 d . . . . .
H8A H 0.4057 0.2147 0.2852 0.021 Uiso 1 1 calc R U . . .
H8B H 0.4795 0.1627 0.2184 0.021 Uiso 1 1 calc R U . . .
C9 C 0.51212(14) 0.33872(17) 0.26123(14) 0.0228(4) Uani 1 1 d . . . . .
H9A H 0.5436 0.3614 0.2059 0.034 Uiso 1 1 calc R U . . .
H9B H 0.5657 0.3146 0.3187 0.034 Uiso 1 1 calc R U . . .
H9C H 0.4743 0.4078 0.2794 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 B3 1.717(3) . ?
C1 B2 1.718(2) . ?
C1 B4 1.719(2) . ?
C1 B5 1.720(2) . ?
C1 B6 1.722(2) . ?
C1 H1 1.000(18) . ?
B2 F2 1.358(2) . ?
B2 B11 1.778(3) . ?
B2 B7 1.782(3) . ?
B2 B3 1.799(3) . ?
B2 B6 1.804(3) . ?
B3 F3 1.357(2) . ?
B3 B8 1.783(3) . ?
B3 B7 1.784(3) . ?
B3 B4 1.789(3) . ?
B4 F4 1.360(2) . ?
B4 B8 1.772(3) . ?
B4 B9 1.774(3) . ?
B4 B5 1.804(3) . ?
B5 F5 1.358(2) . ?
B5 B10 1.781(3) . ?
B5 B9 1.785(3) . ?
B5 B6 1.790(3) . ?
B6 F6 1.361(2) . ?
B6 B10 1.784(3) . ?
B6 B11 1.785(3) . ?
B7 F7 1.372(2) . ?
B7 B8 1.800(3) . ?
B7 B12 1.808(3) . ?
B7 B11 1.813(3) . ?
B8 F8 1.375(2) . ?
B8 B12 1.812(3) . ?
B8 B9 1.815(3) . ?
B9 F9 1.373(2) . ?
B9 B12 1.803(3) . ?
B9 B10 1.809(3) . ?
B10 F10 1.370(2) . ?
B10 B11 1.799(3) . ?
B10 B12 1.820(3) . ?
B11 F11 1.374(2) . ?
B11 B12 1.804(3) . ?
B12 N1 1.444(2) . ?
N1 H1B 0.743(19) . ?
N1 H1A 0.72(2) . ?
N2 C6 1.513(2) . ?
N2 C2 1.518(2) . ?
N2 C4 1.521(2) . ?
N2 C8 1.525(2) . ?
C2 C3 1.515(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.524(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.521(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.515(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
B3 C1 B2 63.18(11) . . ?
B3 C1 B4 62.76(11) . . ?
B2 C1 B4 114.99(13) . . ?
B3 C1 B5 115.84(13) . . ?
B2 C1 B5 115.27(13) . . ?
B4 C1 B5 63.27(11) . . ?
B3 C1 B6 116.12(13) . . ?
B2 C1 B6 63.26(11) . . ?
B4 C1 B6 115.33(13) . . ?
B5 C1 B6 62.67(11) . . ?
B3 C1 H1 116.9 . . ?
B2 C1 H1 117.4 . . ?
B4 C1 H1 117.5 . . ?
B5 C1 H1 117.2 . . ?
B6 C1 H1 117.1 . . ?
F2 B2 C1 120.33(14) . . ?
F2 B2 B11 126.40(14) . . ?
C1 B2 B11 104.02(13) . . ?
F2 B2 B7 125.84(15) . . ?
C1 B2 B7 104.15(13) . . ?
B11 B2 B7 61.24(11) . . ?
F2 B2 B3 119.35(14) . . ?
C1 B2 B3 58.39(10) . . ?
B11 B2 B3 108.58(13) . . ?
B7 B2 B3 59.74(10) . . ?
F2 B2 B6 119.71(14) . . ?
C1 B2 B6 58.48(10) . . ?
B11 B2 B6 59.79(11) . . ?
B7 B2 B6 108.92(13) . . ?
B3 B2 B6 108.17(13) . . ?
F3 B3 C1 119.36(14) . . ?
F3 B3 B8 127.06(15) . . ?
C1 B3 B8 104.34(13) . . ?
F3 B3 B7 126.80(15) . . ?
C1 B3 B7 104.11(13) . . ?
B8 B3 B7 60.61(11) . . ?
F3 B3 B4 120.10(14) . . ?
C1 B3 B4 58.67(10) . . ?
B8 B3 B4 59.47(11) . . ?
B7 B3 B4 107.77(13) . . ?
F3 B3 B2 119.26(14) . . ?
C1 B3 B2 58.43(10) . . ?
B8 B3 B2 108.16(13) . . ?
B7 B3 B2 59.65(10) . . ?
B4 B3 B2 107.74(13) . . ?
F4 B4 C1 120.29(14) . . ?
F4 B4 B8 126.11(15) . . ?
C1 B4 B8 104.74(13) . . ?
F4 B4 B9 125.11(14) . . ?
C1 B4 B9 104.39(13) . . ?
B8 B4 B9 61.58(11) . . ?
F4 B4 B3 120.34(14) . . ?
C1 B4 B3 58.57(10) . . ?
B8 B4 B3 60.09(11) . . ?
B9 B4 B3 109.20(13) . . ?
F4 B4 B5 118.58(14) . . ?
C1 B4 B5 58.40(10) . . ?
B8 B4 B5 109.27(13) . . ?
B9 B4 B5 59.86(11) . . ?
B3 B4 B5 108.30(13) . . ?
F5 B5 C1 118.59(15) . . ?
F5 B5 B10 128.12(15) . . ?
C1 B5 B10 104.38(13) . . ?
F5 B5 B9 126.89(15) . . ?
C1 B5 B9 103.87(13) . . ?
B10 B5 B9 60.97(11) . . ?
F5 B5 B6 119.92(15) . . ?
C1 B5 B6 58.71(10) . . ?
B10 B5 B6 59.93(10) . . ?
B9 B5 B6 108.57(13) . . ?
F5 B5 B4 118.38(14) . . ?
C1 B5 B4 58.33(10) . . ?
B10 B5 B4 108.09(13) . . ?
B9 B5 B4 59.25(11) . . ?
B6 B5 B4 107.98(13) . . ?
F6 B6 C1 119.91(14) . . ?
F6 B6 B10 127.10(15) . . ?
C1 B6 B10 104.19(13) . . ?
F6 B6 B11 126.58(14) . . ?
C1 B6 B11 103.55(13) . . ?
B10 B6 B11 60.53(11) . . ?
F6 B6 B5 120.33(14) . . ?
C1 B6 B5 58.62(10) . . ?
B10 B6 B5 59.78(11) . . ?
B11 B6 B5 107.88(13) . . ?
F6 B6 B2 119.07(14) . . ?
C1 B6 B2 58.26(10) . . ?
B10 B6 B2 108.03(13) . . ?
B11 B6 B2 59.39(11) . . ?
B5 B6 B2 107.81(13) . . ?
F7 B7 B2 120.62(14) . . ?
F7 B7 B3 121.47(14) . . ?
B2 B7 B3 60.61(11) . . ?
F7 B7 B8 122.62(14) . . ?
B2 B7 B8 108.18(13) . . ?
B3 B7 B8 59.67(10) . . ?
F7 B7 B12 122.76(14) . . ?
B2 B7 B12 107.45(13) . . ?
B3 B7 B12 107.83(13) . . ?
B8 B7 B12 60.31(10) . . ?
F7 B7 B11 121.62(14) . . ?
B2 B7 B11 59.27(10) . . ?
B3 B7 B11 107.71(13) . . ?
B8 B7 B11 107.93(13) . . ?
B12 B7 B11 59.77(10) . . ?
F8 B8 B4 121.69(14) . . ?
F8 B8 B3 121.96(15) . . ?
B4 B8 B3 60.44(11) . . ?
F8 B8 B7 122.28(14) . . ?
B4 B8 B7 107.83(13) . . ?
B3 B8 B7 59.72(10) . . ?
F8 B8 B12 122.13(14) . . ?
B4 B8 B12 107.13(13) . . ?
B3 B8 B12 107.68(13) . . ?
B7 B8 B12 60.06(10) . . ?
F8 B8 B9 121.75(14) . . ?
B4 B8 B9 59.27(11) . . ?
B3 B8 B9 107.65(13) . . ?
B7 B8 B9 107.60(13) . . ?
B12 B8 B9 59.62(10) . . ?
F9 B9 B4 120.61(14) . . ?
F9 B9 B5 120.47(15) . . ?
B4 B9 B5 60.90(11) . . ?
F9 B9 B12 123.28(14) . . ?
B4 B9 B12 107.42(13) . . ?
B5 B9 B12 107.89(13) . . ?
F9 B9 B10 122.06(14) . . ?
B4 B9 B10 108.16(13) . . ?
B5 B9 B10 59.40(10) . . ?
B12 B9 B10 60.52(10) . . ?
F9 B9 B8 122.05(15) . . ?
B4 B9 B8 59.14(11) . . ?
B5 B9 B8 108.16(13) . . ?
B12 B9 B8 60.10(10) . . ?
B10 B9 B8 108.52(13) . . ?
F10 B10 B5 123.22(15) . . ?
F10 B10 B6 122.60(15) . . ?
B5 B10 B6 60.28(11) . . ?
F10 B10 B11 121.30(14) . . ?
B5 B10 B11 107.68(13) . . ?
B6 B10 B11 59.78(10) . . ?
F10 B10 B9 121.99(14) . . ?
B5 B10 B9 59.63(11) . . ?
B6 B10 B9 107.79(13) . . ?
B11 B10 B9 107.34(13) . . ?
F10 B10 B12 120.74(14) . . ?
B5 B10 B12 107.34(13) . . ?
B6 B10 B12 107.66(13) . . ?
B11 B10 B12 59.80(10) . . ?
B9 B10 B12 59.58(10) . . ?
F11 B11 B2 121.61(14) . . ?
F11 B11 B6 121.42(14) . . ?
B2 B11 B6 60.82(11) . . ?
F11 B11 B10 121.32(14) . . ?
B2 B11 B10 108.49(13) . . ?
B6 B11 B10 59.69(10) . . ?
F11 B11 B12 121.65(14) . . ?
B2 B11 B12 107.79(13) . . ?
B6 B11 B12 108.29(13) . . ?
B10 B11 B12 60.69(10) . . ?
F11 B11 B7 121.68(14) . . ?
B2 B11 B7 59.49(11) . . ?
B6 B11 B7 108.35(13) . . ?
B10 B11 B7 108.62(13) . . ?
B12 B11 B7 59.96(10) . . ?
N1 B12 B9 122.77(15) . . ?
N1 B12 B11 121.99(15) . . ?
B9 B12 B11 107.37(13) . . ?
N1 B12 B7 120.40(14) . . ?
B9 B12 B7 107.78(13) . . ?
B11 B12 B7 60.27(10) . . ?
N1 B12 B8 120.85(15) . . ?
B9 B12 B8 60.28(10) . . ?
B11 B12 B8 107.79(13) . . ?
B7 B12 B8 59.63(10) . . ?
N1 B12 B10 123.12(15) . . ?
B9 B12 B10 59.90(10) . . ?
B11 B12 B10 59.51(10) . . ?
B7 B12 B10 107.93(13) . . ?
B8 B12 B10 108.17(13) . . ?
B12 N1 H1B 114.5(15) . . ?
B12 N1 H1A 114.7(16) . . ?
H1B N1 H1A 112(2) . . ?
C6 N2 C2 111.08(12) . . ?
C6 N2 C4 110.72(12) . . ?
C2 N2 C4 106.58(12) . . ?
C6 N2 C8 106.38(12) . . ?
C2 N2 C8 111.15(12) . . ?
C4 N2 C8 110.99(12) . . ?
C3 C2 N2 114.77(14) . . ?
C3 C2 H2A 108.6 . . ?
N2 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
N2 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 C5 114.77(14) . . ?
N2 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
N2 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 114.83(14) . . ?
N2 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
N2 C6 H6B 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N2 115.00(14) . . ?
C9 C8 H8A 108.5 . . ?
N2 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
N2 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

