# 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_LEL002_0m
_database_code_depnum_ccdc_archive 'CCDC 1046629'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;
_audit_creation_date             2015-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C18 H B F15, C9 H18 N'
_chemical_formula_sum            'C27 H19 B F15 N'
_chemical_formula_weight         653.26
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.2625(4)
_cell_length_b                   18.4212(7)
_cell_length_c                   14.2535(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.910(2)
_cell_angle_gamma                90
_cell_volume                     2645.89(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9970
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.21
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0432 before and 0.0363 after correction.
The Ratio of minimum to maximum transmission is 0.9482.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6397
_exptl_crystal_density_meas      .
_exptl_crystal_description       Block
_exptl_crystal_F_000             1313.3236
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24700
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.83
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -12
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -8
_reflns_number_gt                3733
_reflns_number_total             4654
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         1.0184
_refine_diff_density_min         -0.2697
_refine_diff_density_rms         0.0554
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             11.1442
_refine_ls_goodness_of_fit_ref   1.0542
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.0542
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+1.3233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1006
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1a), C26(H26), C25(H25), C22(H22), B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27a,H27b), C23(H23a,H23b), C20(H20a,H20b), C19(H19a,H19b)
2.c Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c), C21(H21a,H21b,H21c)
;
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
F8 F 0.62824(14) 0.47411(7) 0.77072(12) 0.0606(4) Uani 1.000000 .
F13 F 0.83328(14) 0.00704(7) 1.05121(8) 0.0494(4) Uani 1.000000 .
F14 F 0.93513(12) 0.12924(7) 0.98638(9) 0.0465(3) Uani 1.000000 .
F15 F 0.80140(11) 0.20219(6) 0.83931(8) 0.0340(3) Uani 1.000000 .
F11 F 0.45201(11) 0.03037(6) 0.81335(8) 0.0357(3) Uani 1.000000 .
F12 F 0.59060(13) -0.04265(6) 0.96035(9) 0.0419(3) Uani 1.000000 .
F10 F 0.48085(13) 0.25469(7) 0.88040(8) 0.0437(3) Uani 1.000000 .
F9 F 0.52756(16) 0.39617(8) 0.90510(10) 0.0606(4) Uani 1.000000 .
F7 F 0.68210(13) 0.40516(7) 0.61414(10) 0.0498(4) Uani 1.000000 .
F6 F 0.63734(12) 0.26542(6) 0.58781(8) 0.0356(3) Uani 1.000000 .
F5 F 0.78568(11) 0.11512(7) 0.67722(8) 0.0359(3) Uani 1.000000 .
F4 F 0.82005(14) 0.05883(8) 0.51196(9) 0.0532(4) Uani 1.000000 .
F3 F 0.61122(17) 0.04439(8) 0.36397(9) 0.0604(4) Uani 1.000000 .
F2 F 0.36454(15) 0.08511(8) 0.38743(9) 0.0607(4) Uani 1.000000 .
F1 F 0.32592(12) 0.13960(8) 0.55345(9) 0.0474(3) Uani 1.000000 .
N1 N 0.16132(16) 0.22236(9) 0.71240(11) 0.0284(4) Uani 1.000000 .
C27 C -0.0444(2) 0.26867(13) 0.63445(18) 0.0472(6) Uani 1.000000 .
C26 C 0.0818(2) 0.23569(12) 0.61213(14) 0.0361(5) Uani 1.000000 .
C25 C 0.1130(2) 0.16367(11) 0.77192(15) 0.0361(5) Uani 1.000000 .
C24 C 0.1939(3) 0.16606(13) 0.87267(16) 0.0476(6) Uani 1.000000 .
C23 C 0.0047(2) 0.31339(13) 0.72610(18) 0.0467(6) Uani 1.000000 .
C22 C 0.1539(2) 0.30095(11) 0.74392(14) 0.0355(5) Uani 1.000000 .
C21 C 0.1223(2) 0.09086(12) 0.72490(18) 0.0446(6) Uani 1.000000 .
C20 C 0.1647(2) 0.29427(12) 0.57723(15) 0.0404(5) Uani 1.000000 .
C19 C 0.2129(2) 0.34045(12) 0.66740(15) 0.0381(5) Uani 1.000000 .
C10 C 0.6042(2) 0.40299(11) 0.75926(17) 0.0382(5) Uani 1.000000 .
C11 C 0.5546(2) 0.36354(12) 0.82662(15) 0.0378(5) Uani 1.000000 .
C12 C 0.53256(19) 0.29019(11) 0.81190(14) 0.0305(5) Uani 1.000000 .
C7 C 0.55843(18) 0.25153(10) 0.73388(13) 0.0241(4) Uani 1.000000 .
C13 C 0.61811(18) 0.12074(10) 0.81816(12) 0.0229(4) Uani 1.000000 .
C18 C 0.74285(19) 0.14152(10) 0.86612(12) 0.0248(4) Uani 1.000000 .
C17 C 0.8155(2) 0.10443(11) 0.94261(13) 0.0300(5) Uani 1.000000 .
C16 C 0.7635(2) 0.04286(11) 0.97540(13) 0.0315(5) Uani 1.000000 .
C14 C 0.57163(19) 0.05772(10) 0.85404(13) 0.0257(4) Uani 1.000000 .
C15 C 0.6411(2) 0.01869(10) 0.93058(13) 0.0286(4) Uani 1.000000 .
C9 C 0.63123(19) 0.36801(11) 0.68029(15) 0.0338(5) Uani 1.000000 .
C8 C 0.60745(18) 0.29453(10) 0.66858(13) 0.0272(4) Uani 1.000000 .
C1 C 0.55336(19) 0.12818(10) 0.62563(12) 0.0244(4) Uani 1.000000 .
C6 C 0.6759(2) 0.10639(10) 0.60835(13) 0.0276(4) Uani 1.000000 .
C5 C 0.6977(2) 0.07835(11) 0.52285(14) 0.0347(5) Uani 1.000000 .
C4 C 0.5924(2) 0.07140(12) 0.44801(14) 0.0384(5) Uani 1.000000 .
C3 C 0.4688(2) 0.09211(12) 0.46012(14) 0.0387(5) Uani 1.000000 .
C2 C 0.4513(2) 0.11961(11) 0.54741(14) 0.0318(5) Uani 1.000000 .
B1 B 0.5303(2) 0.16386(11) 0.72662(14) 0.0230(5) Uani 1.000000 .
H1a H 0.24858(16) 0.21210(9) 0.70769(11) 0.0340(4) Uiso 1.000000 R
H27a H -0.0883(2) 0.30023(13) 0.58159(18) 0.0566(7) Uiso 1.000000 R
H27b H -0.1074(2) 0.23043(13) 0.64587(18) 0.0566(7) Uiso 1.000000 R
H26 H 0.0675(2) 0.19149(12) 0.57072(14) 0.0433(6) Uiso 1.000000 R
H25 H 0.0179(2) 0.17337(11) 0.77473(15) 0.0434(6) Uiso 1.000000 R
H24a H 0.2876(4) 0.1575(9) 0.87077(19) 0.0714(9) Uiso 1.000000 GR
H24b H 0.1841(13) 0.2138(3) 0.9008(5) 0.0714(9) Uiso 1.000000 GR
H24c H 0.1623(11) 0.1284(6) 0.9115(4) 0.0714(9) Uiso 1.000000 GR
H23a H -0.0170(2) 0.36548(13) 0.71577(18) 0.0560(7) Uiso 1.000000 R
H23b H -0.0343(2) 0.29533(13) 0.78008(18) 0.0560(7) Uiso 1.000000 R
H22 H 0.2003(2) 0.31083(11) 0.81094(14) 0.0426(6) Uiso 1.000000 R
H21a H 0.0648(12) 0.0907(3) 0.6616(5) 0.0668(9) Uiso 1.000000 GR
H21b H 0.2142(4) 0.0820(4) 0.7182(10) 0.0668(9) Uiso 1.000000 GR
H21c H 0.0938(15) 0.05261(15) 0.7644(6) 0.0668(9) Uiso 1.000000 GR
H20a H 0.2405(2) 0.27299(12) 0.55298(15) 0.0485(6) Uiso 1.000000 R
H20b H 0.1106(2) 0.32362(12) 0.52600(15) 0.0485(6) Uiso 1.000000 R
H19a H 0.1792(2) 0.39082(12) 0.65854(15) 0.0457(6) Uiso 1.000000 R
H19b H 0.3110(2) 0.34152(12) 0.68399(15) 0.0457(6) Uiso 1.000000 R
H1 H 0.4347(2) 0.15651(11) 0.72990(14) 0.0276(5) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F8 C10 1.337(2) . ?
F13 C16 1.350(2) . ?
F14 C17 1.348(2) . ?
F15 C18 1.358(2) . ?
F11 C14 1.352(2) . ?
F12 C15 1.345(2) . ?
F10 C12 1.363(2) . ?
F9 C11 1.344(2) . ?
F7 C9 1.348(2) . ?
F6 C8 1.357(2) . ?
F5 C6 1.357(2) . ?
F4 C5 1.343(2) . ?
F3 C4 1.344(2) . ?
F2 C3 1.347(2) . ?
F1 C2 1.357(2) . ?
N1 C26 1.526(2) . ?
N1 C25 1.515(2) . ?
N1 C22 1.522(3) . ?
N1 H1a 0.9300 . ?
C27 C26 1.518(3) . ?
C27 C23 1.546(4) . ?
C27 H27a 0.9900 . ?
C27 H27b 0.9900 . ?
C26 C20 1.515(3) . ?
C26 H26 1.0000 . ?
C25 C24 1.517(3) . ?
C25 C21 1.510(3) . ?
C25 H25 1.0000 . ?
C24 H24a 0.9800 . ?
C24 H24b 0.9800 . ?
C24 H24c 0.9800 . ?
C23 C22 1.521(3) . ?
C23 H23a 0.9900 . ?
C23 H23b 0.9900 . ?
C22 C19 1.528(3) . ?
C22 H22 1.0000 . ?
C21 H21a 0.9800 . ?
C21 H21b 0.9800 . ?
C21 H21c 0.9800 . ?
C20 C19 1.543(3) . ?
C20 H20a 0.9900 . ?
C20 H20b 0.9900 . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
C10 C11 1.376(3) . ?
C10 C9 1.370(3) . ?
C11 C12 1.379(3) . ?
C12 C7 1.388(3) . ?
C7 C8 1.387(3) . ?
C7 B1 1.640(3) . ?
C13 C18 1.386(3) . ?
C13 C14 1.389(3) . ?
C13 B1 1.643(3) . ?
C18 C17 1.380(3) . ?
C17 C16 1.372(3) . ?
C16 C15 1.372(3) . ?
C14 C15 1.386(3) . ?
C9 C8 1.380(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.387(3) . ?
C1 B1 1.640(3) . ?
C6 C5 1.380(3) . ?
C5 C4 1.373(3) . ?
C4 C3 1.367(3) . ?
C3 C2 1.386(3) . ?
B1 H1 1.0000 . ?

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
C25 N1 C26 117.75(15) . . ?
C22 N1 C26 94.35(14) . . ?
C22 N1 C25 118.28(16) . . ?
H1a N1 C26 108.48(11) . . ?
H1a N1 C25 108.48(10) . . ?
H1a N1 C22 108.48(10) . . ?
C23 C27 C26 103.63(17) . . ?
H27a C27 C26 111.03(11) . . ?
H27a C27 C23 111.03(12) . . ?
H27b C27 C26 111.03(12) . . ?
H27b C27 C23 111.03(12) . . ?
H27b C27 H27a 109.0 . . ?
C27 C26 N1 101.22(17) . . ?
C20 C26 N1 100.83(16) . . ?
C20 C26 C27 109.77(18) . . ?
H26 C26 N1 114.49(10) . . ?
H26 C26 C27 114.49(12) . . ?
H26 C26 C20 114.49(12) . . ?
C24 C25 N1 109.32(17) . . ?
C21 C25 N1 109.31(17) . . ?
C21 C25 C24 112.12(18) . . ?
H25 C25 N1 108.67(10) . . ?
H25 C25 C24 108.67(13) . . ?
H25 C25 C21 108.67(12) . . ?
H24a C24 C25 109.5 . . ?
H24b C24 C25 109.5 . . ?
H24b C24 H24a 109.5 . . ?
H24c C24 C25 109.5 . . ?
H24c C24 H24a 109.5 . . ?
H24c C24 H24b 109.5 . . ?
C22 C23 C27 102.59(18) . . ?
H23a C23 C27 111.25(12) . . ?
H23a C23 C22 111.25(12) . . ?
H23b C23 C27 111.25(12) . . ?
H23b C23 C22 111.25(12) . . ?
H23b C23 H23a 109.2 . . ?
C23 C22 N1 101.46(16) . . ?
C19 C22 N1 101.17(16) . . ?
C19 C22 C23 109.33(17) . . ?
H22 C22 N1 114.46(9) . . ?
H22 C22 C23 114.46(12) . . ?
H22 C22 C19 114.46(11) . . ?
H21a C21 C25 109.5 . . ?
H21b C21 C25 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C25 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
C19 C20 C26 103.34(17) . . ?
H20a C20 C26 111.09(13) . . ?
H20a C20 C19 111.09(12) . . ?
H20b C20 C26 111.09(12) . . ?
H20b C20 C19 111.09(11) . . ?
H20b C20 H20a 109.1 . . ?
C20 C19 C22 102.95(16) . . ?
H19a C19 C22 111.17(12) . . ?
H19a C19 C20 111.17(11) . . ?
H19b C19 C22 111.17(11) . . ?
H19b C19 C20 111.17(12) . . ?
H19b C19 H19a 109.1 . . ?
C11 C10 F8 121.1(2) . . ?
C9 C10 F8 120.0(2) . . ?
C9 C10 C11 118.94(18) . . ?
C10 C11 F9 120.42(19) . . ?
C12 C11 F9 120.7(2) . . ?
C12 C11 C10 118.9(2) . . ?
C11 C12 F10 115.83(18) . . ?
C7 C12 F10 119.15(17) . . ?
C7 C12 C11 125.02(19) . . ?
C8 C7 C12 113.15(17) . . ?
B1 C7 C12 119.85(17) . . ?
B1 C7 C8 127.00(17) . . ?
C14 C13 C18 113.50(16) . . ?
B1 C13 C18 125.08(16) . . ?
B1 C13 C14 121.42(16) . . ?
C13 C18 F15 120.34(16) . . ?
C17 C18 F15 115.37(16) . . ?
C17 C18 C13 124.29(18) . . ?
C18 C17 F14 120.43(18) . . ?
C16 C17 F14 120.09(17) . . ?
C16 C17 C18 119.46(18) . . ?
C17 C16 F13 119.68(19) . . ?
C15 C16 F13 120.96(19) . . ?
C15 C16 C17 119.36(17) . . ?
C13 C14 F11 120.05(16) . . ?
C15 C14 F11 115.74(17) . . ?
C15 C14 C13 124.20(18) . . ?
C16 C15 F12 119.96(17) . . ?
C14 C15 F12 120.86(18) . . ?
C14 C15 C16 119.18(18) . . ?
C10 C9 F7 120.09(18) . . ?
C8 C9 F7 119.8(2) . . ?
C8 C9 C10 120.13(19) . . ?
C7 C8 F6 120.83(17) . . ?
C9 C8 F6 115.28(17) . . ?
C9 C8 C7 123.88(19) . . ?
C2 C1 C6 113.38(17) . . ?
B1 C1 C6 123.98(16) . . ?
B1 C1 C2 122.60(17) . . ?
C1 C6 F5 119.63(16) . . ?
C5 C6 F5 115.61(18) . . ?
C5 C6 C1 124.71(18) . . ?
C6 C5 F4 120.89(19) . . ?
C4 C5 F4 120.04(18) . . ?
C4 C5 C6 119.1(2) . . ?
C5 C4 F3 120.1(2) . . ?
C3 C4 F3 120.6(2) . . ?
C3 C4 C5 119.25(19) . . ?
C4 C3 F2 119.80(19) . . ?
C2 C3 F2 120.4(2) . . ?
C2 C3 C4 119.75(19) . . ?
C1 C2 F1 119.94(18) . . ?
C3 C2 F1 116.21(17) . . ?
C3 C2 C1 123.8(2) . . ?
C13 B1 C7 111.23(14) . . ?
C1 B1 C7 113.39(15) . . ?
C1 B1 C13 110.77(15) . . ?
H1 B1 C7 107.03(10) . . ?
H1 B1 C13 107.03(10) . . ?
H1 B1 C1 107.03(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tm103_0ma
_database_code_depnum_ccdc_archive 'CCDC 1046630'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;
_audit_creation_date             2015-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C19 H3 B F15 O, C9 H18 N, 0.5(C Cl2)'
_chemical_formula_sum            'C28.5 H21 B Cl F15 N O'
_chemical_formula_weight         724.74
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y,-z+1/2
4 -x+1/2,-y+1/2,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y,z-1/2
8 x-1/2,y-1/2,-z-1/2

_symmetry_Int_Tables_number      60
_cell_length_a                   17.750(5)
_cell_length_b                   16.032(4)
_cell_length_c                   20.783(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5914(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9681
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.27
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0959 before and 0.0658 after correction.
The Ratio of minimum to maximum transmission is 0.9034.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6278
_exptl_crystal_density_meas      .
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2915.9611
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.1159
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            47407
_diffrn_reflns_theta_full        24.9981
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.71
_diffrn_ambient_temperature      149.7
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              0
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                3516
_reflns_number_total             5198
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.9518
_refine_diff_density_min         -0.6230
_refine_diff_density_rms         0.1465
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             11.8974
_refine_ls_goodness_of_fit_ref   1.0628
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     440
_refine_ls_number_reflns         5198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0811
_refine_ls_restrained_S_all      1.0628
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0916P)²+37.3813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2300
_refine_ls_wR_factor_ref         0.2505
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Cl1b(0.5) Cl1a(0.5)
3.a Ternary CH refined with riding coordinates:
 N1(H1), C20(H20), C23(H23), C26(H26)
3.b Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b), C22(H22a,H22b), C24(H24a,H24b), C25(H25a,H25b)
3.c Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C27(H27a,H27b,H27c), C28(H28a,H28b,H28c)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
F1 F 0.25632(18) 0.6822(2) 0.55692(15) 0.0309(8) Uani 1.000000 1 . . .
F2 F 0.3167(2) 0.8118(2) 0.62054(17) 0.0347(8) Uani 1.000000 1 . . .
F3 F 0.4508(2) 0.7945(2) 0.68344(18) 0.0426(10) Uani 1.000000 1 . . .
F4 F 0.52181(18) 0.6433(2) 0.68553(16) 0.0376(9) Uani 1.000000 1 . . .
F5 F 0.46024(17) 0.5113(2) 0.62781(15) 0.0289(8) Uani 1.000000 1 . . .
F6 F 0.31107(18) 0.4181(2) 0.65340(14) 0.0296(8) Uani 1.000000 1 . . .
F7 F 0.3533(2) 0.2593(2) 0.67009(17) 0.0406(9) Uani 1.000000 1 . . .
F8 F 0.4324(2) 0.1777(2) 0.5760(2) 0.0456(10) Uani 1.000000 1 . . .
F9 F 0.4674(2) 0.2604(2) 0.46461(18) 0.0410(9) Uani 1.000000 1 . . .
F10 F 0.4152(2) 0.4123(2) 0.44274(16) 0.0359(9) Uani 1.000000 1 . . .
F11 F 0.2297(2) 0.4207(2) 0.45149(16) 0.0378(9) Uani 1.000000 1 . . .
F12 F 0.0835(2) 0.3819(3) 0.4591(2) 0.0603(12) Uani 1.000000 1 . . .
F13 F -0.0014(2) 0.4328(3) 0.5623(2) 0.0611(13) Uani 1.000000 1 . . .
F14 F 0.0665(2) 0.5222(2) 0.6587(2) 0.0493(11) Uani 1.000000 1 . . .
F15 F 0.2116(2) 0.5639(2) 0.65115(16) 0.0355(8) Uani 1.000000 1 . . .
O1 O 0.3299(2) 0.5528(2) 0.47244(17) 0.0244(9) Uani 1.000000 1 . . .
C1 C 0.3541(3) 0.5891(3) 0.5896(2) 0.0214(11) Uani 1.000000 1 . . .
C2 C 0.3216(3) 0.6678(4) 0.5898(3) 0.0251(12) Uani 1.000000 1 . . .
C3 C 0.3507(3) 0.7355(3) 0.6222(3) 0.0245(12) Uani 1.000000 1 . . .
C4 C 0.4200(3) 0.7278(3) 0.6549(3) 0.0263(13) Uani 1.000000 1 . . .
C5 C 0.4536(3) 0.6509(4) 0.6560(3) 0.0271(13) Uani 1.000000 1 . . .
C6 C 0.4215(3) 0.5840(3) 0.6244(3) 0.0223(12) Uani 1.000000 1 . . .
C7 C 0.3604(3) 0.4247(3) 0.5476(2) 0.0206(11) Uani 1.000000 1 . . .
C8 C 0.3490(3) 0.3803(3) 0.6043(3) 0.0235(12) Uani 1.000000 1 . . .
C9 C 0.3708(3) 0.2983(4) 0.6143(3) 0.0263(13) Uani 1.000000 1 . . .
C10 C 0.4107(3) 0.2585(3) 0.5680(3) 0.0268(13) Uani 1.000000 1 . . .
C11 C 0.4258(3) 0.2988(4) 0.5108(3) 0.0294(13) Uani 1.000000 1 . . .
C12 C 0.3996(3) 0.3792(4) 0.5018(3) 0.0244(12) Uani 1.000000 1 . . .
C13 C 0.2283(3) 0.4983(3) 0.5488(3) 0.0218(11) Uani 1.000000 1 . . .
C14 C 0.1907(3) 0.4498(4) 0.5034(3) 0.0274(13) Uani 1.000000 1 . . .
C15 C 0.1145(3) 0.4281(4) 0.5071(3) 0.0364(15) Uani 1.000000 1 . . .
C16 C 0.0729(3) 0.4538(4) 0.5584(3) 0.0392(16) Uani 1.000000 1 . . .
C17 C 0.1071(3) 0.4985(4) 0.6063(3) 0.0337(14) Uani 1.000000 1 . . .
C18 C 0.1828(3) 0.5207(3) 0.6007(3) 0.0252(12) Uani 1.000000 1 . . .
C19 C 0.4014(3) 0.5919(4) 0.4591(3) 0.0319(14) Uani 1.000000 1 . . .
H19a H 0.4421(4) 0.5580(14) 0.4773(17) 0.048(2) Uiso 1.000000 1 GR . .
H19b H 0.4082(11) 0.597(2) 0.4124(3) 0.048(2) Uiso 1.000000 1 GR . .
H19c H 0.4024(9) 0.6476(11) 0.4785(17) 0.048(2) Uiso 1.000000 1 GR . .
B1B B 0.3201(3) 0.5181(4) 0.5385(3) 0.0215(13) Uani 1.000000 1 . . .
N1 N 0.2536(3) 0.5684(3) 0.3496(2) 0.0353(12) Uani 1.000000 1 . . .
H1 H 0.2779(3) 0.5557(3) 0.3881(2) 0.0424(15) Uiso 1.000000 1 R . .
C20 C 0.1684(4) 0.5706(4) 0.3599(3) 0.0395(16) Uani 1.000000 1 . . .
H20 H 0.1457(4) 0.5154(4) 0.3708(3) 0.0474(19) Uiso 1.000000 1 R . .
C21 C 0.1393(4) 0.6085(5) 0.2982(3) 0.0497(19) Uani 1.000000 1 . . .
H21a H 0.1337(4) 0.5658(5) 0.2642(3) 0.060(2) Uiso 1.000000 1 R . .
H21b H 0.0904(4) 0.6368(5) 0.3049(3) 0.060(2) Uiso 1.000000 1 R . .
C22 C 0.2029(4) 0.6726(4) 0.2811(3) 0.0449(17) Uani 1.000000 1 . . .
H22a H 0.2256(4) 0.6598(4) 0.2387(3) 0.054(2) Uiso 1.000000 1 R . .
H22b H 0.1830(4) 0.7303(4) 0.2804(3) 0.054(2) Uiso 1.000000 1 R . .
C23 C 0.2605(4) 0.6609(4) 0.3355(3) 0.0402(16) Uani 1.000000 1 . . .
H23 H 0.3127(4) 0.6800(4) 0.3248(3) 0.0483(19) Uiso 1.000000 1 R . .
C24 C 0.2282(4) 0.6975(4) 0.3984(3) 0.0403(16) Uani 1.000000 1 . . .
H24a H 0.2667(4) 0.6987(4) 0.4329(3) 0.0484(19) Uiso 1.000000 1 R . .
H24b H 0.2083(4) 0.7545(4) 0.3917(3) 0.0484(19) Uiso 1.000000 1 R . .
C25 C 0.1642(4) 0.6352(4) 0.4144(3) 0.0387(15) Uani 1.000000 1 . . .
H25a H 0.1146(4) 0.6635(4) 0.4147(3) 0.0465(18) Uiso 1.000000 1 R . .
H25b H 0.1726(4) 0.6086(4) 0.4567(3) 0.0465(18) Uiso 1.000000 1 R . .
C26 C 0.2826(5) 0.5115(5) 0.2954(3) 0.050(2) Uani 1.000000 1 . . .
H26 H 0.2586(5) 0.5293(5) 0.2542(3) 0.060(2) Uiso 1.000000 1 R . .
C27 C 0.2654(8) 0.4209(5) 0.3060(4) 0.093(4) Uani 1.000000 1 . . .
H27a H 0.281(4) 0.4047(14) 0.3495(15) 0.140(6) Uiso 1.000000 1 GR . .
H27b H 0.2112(10) 0.4115(10) 0.301(4) 0.140(6) Uiso 1.000000 1 GR . .
H27c H 0.293(4) 0.3872(6) 0.274(3) 0.140(6) Uiso 1.000000 1 GR . .
C28 C 0.3694(5) 0.5231(7) 0.2891(4) 0.087(4) Uani 1.000000 1 . . .
H28a H 0.3942(6) 0.502(4) 0.3281(16) 0.130(5) Uiso 1.000000 1 GR . .
H28b H 0.3877(8) 0.492(4) 0.252(2) 0.130(5) Uiso 1.000000 1 GR . .
H28c H 0.3810(6) 0.5824(9) 0.284(4) 0.130(5) Uiso 1.000000 1 GR . .
Cl1a Cl -0.0594(4) 0.2985(6) 0.1887(3) 0.111(2) Uani 0.500000 1 . . .
Cl1b Cl 0.0290(4) 0.2231(7) 0.2898(5) 0.171(5) Uani 0.500000 1 . . .
C0aa C 0.0 0.3160(10) 0.25 0.077(4) Uani 1.000000 2 S T P


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
F1 C2 1.365(6) . ?
F2 C3 1.366(6) . ?
F3 C4 1.340(6) . ?
F4 C5 1.362(6) . ?
F5 C6 1.355(6) . ?
F6 C8 1.364(6) . ?
F7 C9 1.353(6) . ?
F8 C10 1.360(6) . ?
F9 C11 1.358(6) . ?
F10 C12 1.366(6) . ?
F11 C14 1.363(7) . ?
F12 C15 1.358(7) . ?
F13 C16 1.363(7) . ?
F14 C17 1.359(7) . ?
F15 C18 1.357(7) . ?
O1 C19 1.442(7) . ?
O1 B1B 1.491(7) . ?
C1 C2 1.388(8) . ?
C1 C6 1.400(7) . ?
C1 B1B 1.670(8) . ?
C2 C3 1.378(8) . ?
C3 C4 1.410(8) . ?
C4 C5 1.371(8) . ?
C5 C6 1.381(8) . ?
C7 C8 1.391(8) . ?
C7 C12 1.387(8) . ?
C7 B1B 1.671(8) . ?
C8 C9 1.387(8) . ?
C9 C10 1.355(8) . ?
C10 C11 1.379(9) . ?
C11 C12 1.383(8) . ?
C13 C14 1.392(8) . ?
C13 C18 1.395(8) . ?
C13 B1B 1.673(8) . ?
C14 C15 1.399(8) . ?
C15 C16 1.361(10) . ?
C16 C17 1.369(10) . ?
C17 C18 1.395(8) . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
N1 H1 0.9300 . ?
N1 C20 1.528(8) . ?
N1 C23 1.517(8) . ?
N1 C26 1.538(8) . ?
C20 H20 1.0000 . ?
C20 C21 1.510(9) . ?
C20 C25 1.534(9) . ?
C21 H21a 0.9900 . ?
C21 H21b 0.9900 . ?
C21 C22 1.567(11) . ?
C22 H22a 0.9900 . ?
C22 H22b 0.9900 . ?
C22 C23 1.536(9) . ?
C23 H23 1.0000 . ?
C23 C24 1.544(9) . ?
C24 H24a 0.9900 . ?
C24 H24b 0.9900 . ?
C24 C25 1.549(9) . ?
C25 H25a 0.9900 . ?
C25 H25b 0.9900 . ?
C26 H26 1.0000 . ?
C26 C27 1.501(11) . ?
C26 C28 1.557(13) . ?
C27 H27a 0.9800 . ?
C27 H27b 0.9800 . ?
C27 H27c 0.9800 . ?
C28 H28a 0.9800 . ?
C28 H28b 0.9800 . ?
C28 H28c 0.9800 . ?
Cl1a Cl1b 1.398(13) 3 ?
Cl1a C0aa 1.677(7) 3 ?
Cl1b Cl1b 1.95(2) 3 ?
Cl1b C0aa 1.780(15) . ?

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
B1B O1 C19 116.3(4) . . ?
C6 C1 C2 114.0(5) . . ?
B1B C1 C2 118.1(5) . . ?
B1B C1 C6 126.7(5) . . ?
C1 C2 F1 120.3(5) . . ?
C3 C2 F1 115.5(5) . . ?
C3 C2 C1 124.2(5) . . ?
C2 C3 F2 121.8(5) . . ?
C4 C3 F2 118.4(5) . . ?
C4 C3 C2 119.6(5) . . ?
C3 C4 F3 120.0(5) . . ?
C5 C4 F3 122.2(5) . . ?
C5 C4 C3 117.8(5) . . ?
C4 C5 F4 118.4(5) . . ?
C6 C5 F4 120.8(5) . . ?
C6 C5 C4 120.7(5) . . ?
C1 C6 F5 120.7(5) . . ?
C5 C6 F5 115.6(5) . . ?
C5 C6 C1 123.6(5) . . ?
C12 C7 C8 112.7(5) . . ?
B1B C7 C8 119.5(5) . . ?
B1B C7 C12 127.5(5) . . ?
C7 C8 F6 118.6(5) . . ?
C9 C8 F6 116.5(5) . . ?
C9 C8 C7 124.8(5) . . ?
C8 C9 F7 120.1(5) . . ?
C10 C9 F7 120.8(5) . . ?
C10 C9 C8 119.1(5) . . ?
C9 C10 F8 120.6(5) . . ?
C11 C10 F8 119.8(5) . . ?
C11 C10 C9 119.5(5) . . ?
C10 C11 F9 120.2(5) . . ?
C12 C11 F9 120.6(5) . . ?
C12 C11 C10 119.2(5) . . ?
C7 C12 F10 120.9(5) . . ?
C11 C12 F10 114.5(5) . . ?
C11 C12 C7 124.5(5) . . ?
C18 C13 C14 113.0(5) . . ?
B1B C13 C14 119.0(5) . . ?
B1B C13 C18 127.9(5) . . ?
C13 C14 F11 119.0(5) . . ?
C15 C14 F11 116.6(5) . . ?
C15 C14 C13 124.4(6) . . ?
C14 C15 F12 119.2(6) . . ?
C16 C15 F12 121.4(5) . . ?
C16 C15 C14 119.5(6) . . ?
C15 C16 F13 119.7(6) . . ?
C17 C16 F13 121.0(6) . . ?
C17 C16 C15 119.2(5) . . ?
C16 C17 F14 119.6(5) . . ?
C18 C17 F14 120.4(6) . . ?
C18 C17 C16 120.0(6) . . ?
C13 C18 F15 120.7(5) . . ?
C17 C18 F15 115.4(5) . . ?
C17 C18 C13 123.8(5) . . ?
H19a C19 O1 109.5 . . ?
H19b C19 O1 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 O1 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
C1 B1B O1 106.8(4) . . ?
C7 B1B O1 112.9(4) . . ?
C7 B1B C1 112.5(4) . . ?
C13 B1B O1 107.6(4) . . ?
C13 B1B C1 113.5(4) . . ?
C13 B1B C7 103.4(4) . . ?
C20 N1 H1 110.1(3) . . ?
C23 N1 H1 110.1(3) . . ?
C23 N1 C20 94.8(5) . . ?
C26 N1 H1 110.1(3) . . ?
C26 N1 C20 116.6(5) . . ?
C26 N1 C23 114.2(5) . . ?
H20 C20 N1 114.3(3) . . ?
C21 C20 N1 103.2(5) . . ?
C21 C20 H20 114.3(4) . . ?
C25 C20 N1 99.6(5) . . ?
C25 C20 H20 114.3(4) . . ?
C25 C20 C21 109.8(6) . . ?
H21a C21 C20 111.3(4) . . ?
H21b C21 C20 111.3(4) . . ?
H21b C21 H21a 109.2 . . ?
C22 C21 C20 102.2(6) . . ?
C22 C21 H21a 111.3(4) . . ?
C22 C21 H21b 111.3(4) . . ?
H22a C22 C21 111.1(4) . . ?
H22b C22 C21 111.1(4) . . ?
H22b C22 H22a 109.0 . . ?
C23 C22 C21 103.4(5) . . ?
C23 C22 H22a 111.1(4) . . ?
C23 C22 H22b 111.1(4) . . ?
C22 C23 N1 102.0(5) . . ?
H23 C23 N1 114.6(3) . . ?
H23 C23 C22 114.6(4) . . ?
C24 C23 N1 100.2(5) . . ?
C24 C23 C22 109.3(6) . . ?
C24 C23 H23 114.6(4) . . ?
H24a C24 C23 111.4(4) . . ?
H24b C24 C23 111.4(3) . . ?
H24b C24 H24a 109.2 . . ?
C25 C24 C23 102.1(5) . . ?
C25 C24 H24a 111.4(3) . . ?
C25 C24 H24b 111.4(3) . . ?
C24 C25 C20 104.0(5) . . ?
H25a C25 C20 111.0(3) . . ?
H25a C25 C24 111.0(3) . . ?
H25b C25 C20 111.0(3) . . ?
H25b C25 C24 111.0(3) . . ?
H25b C25 H25a 109.0 . . ?
H26 C26 N1 108.4(3) . . ?
C27 C26 N1 113.5(6) . . ?
C27 C26 H26 108.4(5) . . ?
C28 C26 N1 108.8(6) . . ?
C28 C26 H26 108.4(4) . . ?
C28 C26 C27 109.2(8) . . ?
H27a C27 C26 109.5 . . ?
H27b C27 C26 109.5 . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 C26 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?
H28a C28 C26 109.5 . . ?
H28b C28 C26 109.5 . . ?
H28b C28 H28a 109.5 . . ?
H28c C28 C26 109.5 . . ?
H28c C28 H28a 109.5 . . ?
H28c C28 H28b 109.5 . . ?
C0aa Cl1a Cl1b 70.1(7) 3 3 ?
Cl1b Cl1b Cl1a 118.4(5) 3 3 ?
C0aa Cl1b Cl1a 62.4(5) . 3 ?
Cl1a C0aa Cl1a 160.7(12) . 3 ?
Cl1b C0aa Cl1a 113.2(10) . . ?
Cl1b C0aa Cl1a 47.6(5) 3 . ?
Cl1b C0aa Cl1a 113.2(10) 3 3 ?
Cl1b C0aa Cl1a 47.6(5) . 3 ?
Cl1b C0aa Cl1b 66.3(10) 3 . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sad
_database_code_depnum_ccdc_archive 'CCDC 1046631'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;
_audit_creation_date             2015-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C18 H B F15, C14 H20 N'
_chemical_formula_sum            'C32 H21 B F15 N'
_chemical_formula_weight         715.33
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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

_symmetry_Int_Tables_number      61
_cell_length_a                   18.886(4)
_cell_length_b                   16.050(3)
_cell_length_c                   19.128(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5798(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150
_cell_measurement_reflns_used    6317
_cell_measurement_theta_max      23.49
_cell_measurement_theta_min      2.72
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0630 before and 0.0430 after correction.
The Ratio of minimum to maximum transmission is 0.9104.
The λ/2 correction factor is Not present.
;
_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6388
_exptl_crystal_density_meas      .
_exptl_crystal_F_000             2882.7531
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_ambient_temperature      150
_diffrn_reflns_number            50412
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.98
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9908
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              24
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                4257
_reflns_number_total             6654
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         1.9550
_refine_diff_density_min         -0.7437
_refine_diff_density_rms         0.1230
_refine_ls_d_res_high            0.7677
_refine_ls_d_res_low             10.3040
_refine_ls_goodness_of_fit_ref   1.0743
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0687
_refine_ls_restrained_S_all      1.0743
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0726P)²+10.7403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1912
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: N1(0.5) H1a(0.5)
3.a Ternary CH refined with riding coordinates:
 B1(H1), C19(H19), C23(H23), C25(H25), N1(H1a)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20a,H20b), C21(H21a,H21b), C22(H22a,H22b), C24(H24a,H24b)
3.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
3.d Idealised Me refined as rotating group:
 C32(H32a,H32b,H32c)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
F5 F 0.48671(11) 0.72075(13) 0.29496(12) 0.0390(5) Uani 1.000000 .
F1 F 0.27877(12) 0.84121(14) 0.19888(12) 0.0439(6) Uani 1.000000 .
F2 F 0.25743(12) 0.70405(15) 0.12438(11) 0.0438(6) Uani 1.000000 .
F3 F 0.34891(13) 0.57335(14) 0.13358(12) 0.0459(6) Uani 1.000000 .
F4 F 0.46380(12) 0.58490(13) 0.21917(13) 0.0439(6) Uani 1.000000 .
F6 F 0.45455(13) 0.88686(14) 0.14820(12) 0.0443(6) Uani 1.000000 .
F7 F 0.45498(12) 1.01990(15) 0.06597(11) 0.0437(6) Uani 1.000000 .
F8 F 0.39897(13) 1.16834(13) 0.11147(11) 0.0414(6) Uani 1.000000 .
F9 F 0.34219(14) 1.17636(13) 0.24236(11) 0.0451(6) Uani 1.000000 .
F10 F 0.34492(12) 1.04494(13) 0.32739(10) 0.0370(5) Uani 1.000000 .
F11 F 0.54367(11) 0.88280(14) 0.26991(11) 0.0388(5) Uani 1.000000 .
F12 F 0.64553(11) 0.89438(15) 0.36707(12) 0.0456(6) Uani 1.000000 .
F13 F 0.61112(13) 0.90612(15) 0.50464(12) 0.0481(6) Uani 1.000000 .
F14 F 0.47361(13) 0.89687(16) 0.54562(11) 0.0498(6) Uani 1.000000 .
F15 F 0.37054(12) 0.88289(15) 0.44981(11) 0.0435(6) Uani 1.000000 .
C1 C 0.38417(19) 0.7902(2) 0.25090(19) 0.0296(7) Uani 1.000000 .
C2 C 0.32720(19) 0.7790(2) 0.20563(18) 0.0302(8) Uani 1.000000 .
C3 C 0.31433(19) 0.7092(2) 0.16673(18) 0.0310(8) Uani 1.000000 .
C4 C 0.3606(2) 0.6433(2) 0.17070(18) 0.0305(8) Uani 1.000000 .
C5 C 0.41839(18) 0.6494(2) 0.21399(19) 0.0290(8) Uani 1.000000 .
C6 C 0.42909(19) 0.7210(2) 0.25293(19) 0.0293(7) Uani 1.000000 .
C7 C 0.39695(18) 0.9579(2) 0.24169(18) 0.0280(7) Uani 1.000000 .
C8 C 0.42498(19) 0.9580(2) 0.17501(19) 0.0310(8) Uani 1.000000 .
C9 C 0.42644(19) 1.0259(2) 0.13044(18) 0.0312(8) Uani 1.000000 .
C10 C 0.39837(19) 1.1005(2) 0.15291(18) 0.0290(7) Uani 1.000000 .
C11 C 0.37062(18) 1.1044(2) 0.21935(18) 0.0275(7) Uani 1.000000 .
C12 C 0.37171(18) 1.0350(2) 0.26181(17) 0.0276(7) Uani 1.000000 .
C13 C 0.45238(18) 0.8824(2) 0.35418(17) 0.0264(7) Uani 1.000000 .
C14 C 0.52328(19) 0.8866(2) 0.33855(18) 0.0304(8) Uani 1.000000 .
C15 C 0.57717(19) 0.8937(2) 0.3865(2) 0.0339(8) Uani 1.000000 .
C16 C 0.5593(2) 0.8986(2) 0.45634(19) 0.0329(8) Uani 1.000000 .
C17 C 0.4898(2) 0.8944(2) 0.47704(18) 0.0332(8) Uani 1.000000 .
C18 C 0.43750(19) 0.8863(2) 0.4253(2) 0.0326(8) Uani 1.000000 .
B1 B 0.3895(2) 0.8772(2) 0.2952(2) 0.0274(8) Uani 1.000000 .
H1 H 0.3445(2) 0.8837(2) 0.3201(2) 0.0328(10) Uiso 1.000000 R
C19 C 0.3483(2) 0.3041(2) 0.34809(19) 0.0359(9) Uani 1.000000 .
C20 C 0.4149(2) 0.2609(2) 0.37240(19) 0.0371(9) Uani 1.000000 .
H20a H 0.4083(2) 0.2010(2) 0.37425(19) 0.0445(11) Uiso 1.000000 R
H20b H 0.4544(2) 0.2735(2) 0.34181(19) 0.0445(11) Uiso 1.000000 R
C21 C 0.4270(2) 0.2976(3) 0.4469(2) 0.0397(9) Uani 1.000000 .
H21a H 0.4269(2) 0.2540(3) 0.4820(2) 0.0477(11) Uiso 1.000000 R
H21b H 0.4715(2) 0.3276(3) 0.4494(2) 0.0477(11) Uiso 1.000000 R
C22 C 0.2850(2) 0.2721(3) 0.3881(2) 0.0443(10) Uani 1.000000 .
H22a H 0.2412(2) 0.2931(3) 0.3685(2) 0.0532(12) Uiso 1.000000 R
H22b H 0.2837(2) 0.2117(3) 0.3882(2) 0.0532(12) Uiso 1.000000 R
C23 C 0.3652(2) 0.3555(2) 0.45656(18) 0.0406(10) Uani 1.000000 .
C24 C 0.2976(2) 0.3070(3) 0.4634(2) 0.0462(10) Uani 1.000000 .
H24a H 0.2589(2) 0.3428(3) 0.4778(2) 0.0555(13) Uiso 1.000000 R
H24b H 0.3027(2) 0.2621(3) 0.4970(2) 0.0555(13) Uiso 1.000000 R
C25 C 0.3113(2) 0.4593(2) 0.36749(19) 0.0369(9) Uani 1.000000 .
C26 C 0.3288(2) 0.5323(2) 0.41522(18) 0.0311(8) Uani 1.000000 .
C27 C 0.2866(2) 0.5472(2) 0.4723(2) 0.0373(9) Uani 1.000000 .
H27 H 0.2484(2) 0.5122(2) 0.4813(2) 0.0447(10) Uiso 1.000000 R
C28 C 0.2999(2) 0.6132(3) 0.5165(2) 0.0472(11) Uani 1.000000 .
H28 H 0.2711(2) 0.6222(3) 0.5552(2) 0.0566(13) Uiso 1.000000 R
C29 C 0.3563(2) 0.6661(3) 0.5029(2) 0.0472(11) Uani 1.000000 .
H29 H 0.3653(2) 0.7106(3) 0.5328(2) 0.0566(13) Uiso 1.000000 R
C30 C 0.3989(2) 0.6531(2) 0.4457(2) 0.0396(9) Uani 1.000000 .
H30 H 0.4363(2) 0.6891(2) 0.4364(2) 0.0475(11) Uiso 1.000000 R
C31 C 0.3856(2) 0.5858(2) 0.40193(19) 0.0338(8) Uani 1.000000 .
H31 H 0.4147(2) 0.5764(2) 0.36353(19) 0.0406(10) Uiso 1.000000 R
C32 C 0.3127(2) 0.4812(2) 0.29023(17) 0.0300(8) Uani 1.000000 .
H32a H 0.3606(3) 0.4923(15) 0.2761(3) 0.0451(11) Uiso 1.000000 GR
H32b H 0.2944(12) 0.4354(6) 0.2636(2) 0.0451(11) Uiso 1.000000 GR
H32c H 0.2842(10) 0.5297(9) 0.2822(3) 0.0451(11) Uiso 1.000000 GR
N1 N 0.36233(18) 0.39046(19) 0.38147(15) 0.0367(7) Uani 1.000000 .
H19 H 0.3421(2) 0.3052(2) 0.29723(19) 0.0431(11) Uiso 1.000000 R
H23 H 0.3722(2) 0.3978(2) 0.49285(18) 0.0488(12) Uiso 1.000000 R
H25 H 0.2637(2) 0.4395(2) 0.37915(19) 0.0442(11) Uiso 1.000000 R
H1a H 0.40649(18) 0.40768(19) 0.36906(15) 0.0440(9) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F5 C6 1.353(4) . ?
F1 C2 1.360(4) . ?
F2 C3 1.348(4) . ?
F3 C4 1.347(4) . ?
F4 C5 1.348(4) . ?
F6 C8 1.370(4) . ?
F7 C9 1.349(4) . ?
F8 C10 1.347(4) . ?
F9 C11 1.347(4) . ?
F10 C12 1.362(4) . ?
F11 C14 1.370(4) . ?
F12 C15 1.344(4) . ?
F13 C16 1.352(4) . ?
F14 C17 1.347(4) . ?
F15 C18 1.350(4) . ?
C1 C2 1.393(5) . ?
C1 C6 1.398(5) . ?
C1 B1 1.636(5) . ?
C2 C3 1.367(5) . ?
C3 C4 1.374(5) . ?
C4 C5 1.373(5) . ?
C5 C6 1.384(5) . ?
C7 C8 1.381(5) . ?
C7 C12 1.381(5) . ?
C7 B1 1.657(5) . ?
C8 C9 1.384(5) . ?
C9 C10 1.378(5) . ?
C10 C11 1.376(5) . ?
C11 C12 1.379(5) . ?
C13 C14 1.374(5) . ?
C13 C18 1.390(5) . ?
C13 B1 1.639(5) . ?
C14 C15 1.375(5) . ?
C15 C16 1.379(5) . ?
C16 C17 1.372(5) . ?
C17 C18 1.404(5) . ?
B1 H1 0.9800 . ?
C19 C20 1.509(6) . ?
C19 C22 1.510(6) . ?
C19 N1 1.549(4) . ?
C19 H19 0.9800 . ?
C20 H20a 0.9700 . ?
C20 H20b 0.9700 . ?
C20 C21 1.559(5) . ?
C21 H21a 0.9700 . ?
C21 H21b 0.9700 . ?
C21 C23 1.502(6) . ?
C22 H22a 0.9700 . ?
C22 H22b 0.9700 . ?
C22 C24 1.562(6) . ?
C23 C24 1.501(6) . ?
C23 N1 1.543(5) . ?
C23 H23 0.9800 . ?
C24 H24a 0.9700 . ?
C24 H24b 0.9700 . ?
C25 C26 1.521(5) . ?
C25 C32 1.519(5) . ?
C25 N1 1.490(5) . ?
C25 H25 0.9800 . ?
C26 C27 1.373(5) . ?
C26 C31 1.398(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.378(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.387(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.375(6) . ?
C30 H30 0.9300 . ?
C30 C31 1.389(5) . ?
C31 H31 0.9300 . ?
C32 H32a 0.9600 . ?
C32 H32b 0.9600 . ?
C32 H32c 0.9600 . ?
N1 H1a 0.9100 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 112.6(3) . . ?
B1 C1 C2 118.7(3) . . ?
B1 C1 C6 128.7(3) . . ?
C1 C2 F1 118.9(3) . . ?
C3 C2 F1 115.5(3) . . ?
C3 C2 C1 125.6(3) . . ?
C2 C3 F2 121.3(3) . . ?
C4 C3 F2 119.6(3) . . ?
C4 C3 C2 119.2(3) . . ?
C3 C4 F3 120.5(3) . . ?
C5 C4 F3 120.5(3) . . ?
C5 C4 C3 118.9(3) . . ?
C4 C5 F4 119.7(3) . . ?
C6 C5 F4 120.3(3) . . ?
C6 C5 C4 120.0(3) . . ?
C1 C6 F5 120.5(3) . . ?
C5 C6 F5 115.8(3) . . ?
C5 C6 C1 123.8(3) . . ?
C12 C7 C8 112.9(3) . . ?
B1 C7 C8 127.2(3) . . ?
B1 C7 C12 119.9(3) . . ?
C7 C8 F6 120.1(3) . . ?
C9 C8 F6 114.7(3) . . ?
C9 C8 C7 125.3(3) . . ?
C8 C9 F7 121.0(3) . . ?
C10 C9 F7 120.0(3) . . ?
C10 C9 C8 119.0(3) . . ?
C9 C10 F8 121.0(3) . . ?
C11 C10 F8 120.6(3) . . ?
C11 C10 C9 118.3(3) . . ?
C10 C11 F9 119.5(3) . . ?
C12 C11 F9 120.4(3) . . ?
C12 C11 C10 120.1(3) . . ?
C7 C12 F10 119.3(3) . . ?
C11 C12 F10 116.3(3) . . ?
C11 C12 C7 124.4(3) . . ?
C18 C13 C14 114.1(3) . . ?
B1 C13 C14 124.0(3) . . ?
B1 C13 C18 121.9(3) . . ?
C13 C14 F11 118.7(3) . . ?
C15 C14 F11 115.8(3) . . ?
C15 C14 C13 125.5(3) . . ?
C14 C15 F12 121.8(3) . . ?
C16 C15 F12 120.2(3) . . ?
C16 C15 C14 118.0(3) . . ?
C15 C16 F13 119.3(3) . . ?
C17 C16 F13 120.0(3) . . ?
C17 C16 C15 120.7(3) . . ?
C16 C17 F14 119.7(3) . . ?
C18 C17 F14 122.0(3) . . ?
C18 C17 C16 118.3(3) . . ?
C13 C18 F15 121.8(3) . . ?
C17 C18 F15 114.7(3) . . ?
C17 C18 C13 123.5(3) . . ?
C7 B1 C1 110.6(3) . . ?
C13 B1 C1 116.4(3) . . ?
C13 B1 C7 108.9(3) . . ?
H1 B1 C1 106.81(18) . . ?
H1 B1 C7 106.81(18) . . ?
H1 B1 C13 106.81(18) . . ?
C22 C19 C20 110.3(3) . . ?
N1 C19 C20 98.2(3) . . ?
N1 C19 C22 103.3(3) . . ?
H19 C19 C20 114.5(2) . . ?
H19 C19 C22 114.5(2) . . ?
H19 C19 N1 114.47(17) . . ?
H20a C20 C19 111.1(2) . . ?
H20b C20 C19 111.1(2) . . ?
H20b C20 H20a 109.1 . . ?
C21 C20 C19 103.3(3) . . ?
C21 C20 H20a 111.1(2) . . ?
C21 C20 H20b 111.1(2) . . ?
H21a C21 C20 111.1(2) . . ?
H21b C21 C20 111.1(2) . . ?
H21b C21 H21a 109.0 . . ?
C23 C21 C20 103.4(3) . . ?
C23 C21 H21a 111.1(2) . . ?
C23 C21 H21b 111.1(2) . . ?
H22a C22 C19 111.2(2) . . ?
H22b C22 C19 111.2(2) . . ?
H22b C22 H22a 109.1 . . ?
C24 C22 C19 103.0(3) . . ?
C24 C22 H22a 111.2(2) . . ?
C24 C22 H22b 111.2(2) . . ?
C24 C23 C21 110.5(3) . . ?
N1 C23 C21 97.9(3) . . ?
N1 C23 C24 103.8(3) . . ?
H23 C23 C21 114.3(2) . . ?
H23 C23 C24 114.3(2) . . ?
H23 C23 N1 114.31(18) . . ?
C23 C24 C22 103.6(3) . . ?
H24a C24 C22 111.0(2) . . ?
H24a C24 C23 111.0(2) . . ?
H24b C24 C22 111.0(2) . . ?
H24b C24 C23 111.0(2) . . ?
H24b C24 H24a 109.0 . . ?
C32 C25 C26 113.7(3) . . ?
N1 C25 C26 108.8(3) . . ?
N1 C25 C32 109.5(3) . . ?
H25 C25 C26 108.2(2) . . ?
H25 C25 C32 108.2(2) . . ?
H25 C25 N1 108.2(2) . . ?
C27 C26 C25 119.0(3) . . ?
C31 C26 C25 122.1(3) . . ?
C31 C26 C27 118.9(3) . . ?
H27 C27 C26 119.5(2) . . ?
C28 C27 C26 121.1(4) . . ?
C28 C27 H27 119.5(2) . . ?
H28 C28 C27 120.1(2) . . ?
C29 C28 C27 119.7(4) . . ?
C29 C28 H28 120.1(2) . . ?
H29 C29 C28 119.8(2) . . ?
C30 C29 C28 120.4(4) . . ?
C30 C29 H29 119.8(2) . . ?
H30 C30 C29 120.3(2) . . ?
C31 C30 C29 119.5(4) . . ?
C31 C30 H30 120.3(2) . . ?
C30 C31 C26 120.4(4) . . ?
H31 C31 C26 119.8(2) . . ?
H31 C31 C30 119.8(2) . . ?
H32a C32 C25 109.5 . . ?
H32b C32 C25 109.5 . . ?
H32b C32 H32a 109.5 . . ?
H32c C32 C25 109.5 . . ?
H32c C32 H32a 109.5 . . ?
H32c C32 H32b 109.5 . . ?
C23 N1 C19 93.7(3) . . ?
C25 N1 C19 118.6(3) . . ?
C25 N1 C23 117.4(3) . . ?
H1a N1 C19 108.7(2) . . ?
H1a N1 C23 108.7(2) . . ?
H1a N1 C25 108.7(2) . . ?

_vrf_DIFMX01_ALERT_2_A           
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*2.00 
            _refine_diff_density_max given =      1.955
A Large Reported Max.  (Positive) Residual Density       1.96 eA-3

RESPONSE: 

This residual is not chemically meaningful and is located 0.95 A from N. 
;

####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1046632'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;
_audit_creation_date             2015-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C12 H22 N, C18 H B F15'
_chemical_formula_sum            'C30 H23 B F15 N'
_chemical_formula_weight         693.32
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           ' P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -x+1/2,y+1/2,z+1/2
4 x+1/2,-y+1/2,z

_symmetry_Int_Tables_number      33
_cell_length_a                   19.4606(10)
_cell_length_b                   9.1786(4)
_cell_length_c                   15.6625(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2797.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    7280
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.46
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0443 before and 0.0402 after correction.
The Ratio of minimum to maximum transmission is 0.9206.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.6459
_exptl_crystal_density_meas      .
_exptl_crystal_description       Block
_exptl_crystal_F_000             1401.3548
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13394
_diffrn_reflns_theta_full        24.9998
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.09
_diffrn_ambient_temperature      149.71
_diffrn_measured_fraction_theta_full 0.9411
_diffrn_measured_fraction_theta_max 0.9411
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.878
_reflns_limit_h_max              23
_reflns_limit_h_min              -23
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                4048
_reflns_number_total             4637
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.2374
_refine_diff_density_min         -0.1801
_refine_diff_density_rms         0.0408
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             9.7303
_refine_ls_goodness_of_fit_ref   1.0481
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     423
_refine_ls_number_reflns         4637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.0481
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.2511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0688
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C7(H7), C6(H6), C3(H3), B1(H1c)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C11(H11a,H11b), C12(H12a,H12b), C5(H5a,H5b), C4(H4a,H4b),
 C9(H9a,H9b), C8(H8a,H8b), C2(H2a,H2b), C1(H1a,H1b)
;
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
N1 N -0.30554(9) -0.54001(18) -0.02832(10) 0.0232(4) Uani 1.000000 .
H1 H -0.25903(9) -0.52106(18) -0.03625(10) 0.0278(5) Uiso 1.000000 R
C1 C -0.39890(12) -0.5317(3) 0.06806(14) 0.0349(6) Uani 1.000000 .
H1a H -0.41600(12) -0.4848(3) 0.12087(14) 0.0418(7) Uiso 1.000000 R
H1b H -0.41921(12) -0.6302(3) 0.06327(14) 0.0418(7) Uiso 1.000000 R
C2 C -0.41590(12) -0.4384(3) -0.01136(15) 0.0335(6) Uani 1.000000 .
H2a H -0.44309(12) -0.4948(3) -0.05336(15) 0.0402(7) Uiso 1.000000 R
H2b H -0.44177(12) -0.3497(3) 0.00470(15) 0.0402(7) Uiso 1.000000 R
C3 C -0.34567(11) -0.4000(2) -0.04678(14) 0.0272(5) Uani 1.000000 .
H3 H -0.34564(11) -0.3694(2) -0.10806(14) 0.0326(6) Uiso 1.000000 R
C4 C -0.30818(14) -0.2953(3) 0.01375(16) 0.0383(6) Uani 1.000000 .
H4a H -0.26620(14) -0.2556(3) -0.01331(16) 0.0460(7) Uiso 1.000000 R
H4b H -0.33839(14) -0.2135(3) 0.03072(16) 0.0460(7) Uiso 1.000000 R
C5 C -0.29001(13) -0.3915(3) 0.09130(15) 0.0388(6) Uani 1.000000 .
H5a H -0.23963(13) -0.3981(3) 0.09922(15) 0.0466(7) Uiso 1.000000 R
H5b H -0.31108(13) -0.3530(3) 0.14425(15) 0.0466(7) Uiso 1.000000 R
C6 C -0.32042(12) -0.5387(3) 0.06742(14) 0.0322(6) Uani 1.000000 .
H6 H -0.30063(12) -0.6231(3) 0.09950(14) 0.0387(7) Uiso 1.000000 R
C7 C -0.32316(11) -0.6800(2) -0.07489(13) 0.0240(5) Uani 1.000000 .
H7 H -0.36809(11) -0.7171(2) -0.05281(13) 0.0288(6) Uiso 1.000000 R
C8 C -0.26733(12) -0.7910(2) -0.05372(14) 0.0299(5) Uani 1.000000 .
H8a H -0.22211(12) -0.7529(2) -0.07223(14) 0.0358(7) Uiso 1.000000 R
H8b H -0.26564(12) -0.8064(2) 0.00880(14) 0.0358(7) Uiso 1.000000 R
C9 C -0.28154(12) -0.9353(3) -0.09820(15) 0.0342(6) Uani 1.000000 .
H9a H -0.24359(12) -1.0042(3) -0.08620(15) 0.0410(7) Uiso 1.000000 R
H9b H -0.32454(12) -0.9780(3) -0.07548(15) 0.0410(7) Uiso 1.000000 R
C10 C -0.28824(13) -0.9141(3) -0.19413(16) 0.0374(6) Uani 1.000000 .
H10a H -0.24366(13) -0.8814(3) -0.21780(16) 0.0449(7) Uiso 1.000000 R
H10b H -0.30026(13) -1.0081(3) -0.22131(16) 0.0449(7) Uiso 1.000000 R
C11 C -0.34343(13) -0.8016(3) -0.21449(16) 0.0390(6) Uani 1.000000 .
H11a H -0.34530(13) -0.7862(3) -0.27701(16) 0.0469(8) Uiso 1.000000 R
H11b H -0.38871(13) -0.8392(3) -0.19591(16) 0.0469(8) Uiso 1.000000 R
C12 C -0.32943(12) -0.6561(2) -0.17028(13) 0.0309(5) Uani 1.000000 .
H12a H -0.36745(12) -0.5874(2) -0.18218(13) 0.0371(6) Uiso 1.000000 R
H12b H -0.28636(12) -0.6132(2) -0.19263(13) 0.0371(6) Uiso 1.000000 R
F1 F -0.34417(6) -0.99615(15) -0.52925(9) 0.0400(3) Uani 1.000000 .
F2 F -0.29566(7) -0.82139(16) -0.64911(9) 0.0442(4) Uani 1.000000 .
F3 F -0.38225(8) -0.66348(17) -0.74933(9) 0.0560(4) Uani 1.000000 .
F4 F -0.52133(8) -0.69158(17) -0.72769(10) 0.0570(4) Uani 1.000000 .
F5 F -0.57132(6) -0.87386(16) -0.61092(8) 0.0411(4) Uani 1.000000 .
F6 F -0.47644(7) -1.32213(15) -0.58471(8) 0.0432(4) Uani 1.000000 .
F7 F -0.39873(9) -1.55130(15) -0.54236(10) 0.0569(4) Uani 1.000000 .
F8 F -0.32159(7) -1.54706(15) -0.39734(10) 0.0545(4) Uani 1.000000 .
F9 F -0.32420(8) -1.30781(17) -0.29547(10) 0.0574(5) Uani 1.000000 .
F10 F -0.39995(8) -1.07707(15) -0.33683(10) 0.0508(4) Uani 1.000000 .
F11 F -0.43148(7) -0.79278(14) -0.40823(9) 0.0394(3) Uani 1.000000 .
F12 F -0.48657(8) -0.63775(17) -0.28199(9) 0.0532(4) Uani 1.000000 .
F13 F -0.61229(9) -0.7155(2) -0.21524(10) 0.0701(5) Uani 1.000000 .
F14 F -0.67786(7) -0.9517(2) -0.27646(9) 0.0575(5) Uani 1.000000 .
F15 F -0.62305(7) -1.11156(15) -0.40001(9) 0.0434(4) Uani 1.000000 .
C13 C -0.46077(11) -0.9482(2) -0.56473(13) 0.0253(5) Uani 1.000000 .
C14 C -0.39148(11) -0.9262(2) -0.57944(14) 0.0271(5) Uani 1.000000 .
C15 C -0.36438(12) -0.8355(3) -0.63998(14) 0.0317(6) Uani 1.000000 .
C16 C -0.40777(13) -0.7562(3) -0.69132(14) 0.0347(6) Uani 1.000000 .
C17 C -0.47742(13) -0.7714(3) -0.67988(15) 0.0354(6) Uani 1.000000 .
C18 C -0.50176(11) -0.8669(3) -0.61882(14) 0.0294(5) Uani 1.000000 .
C19 C -0.44388(11) -1.1883(2) -0.46234(13) 0.0257(5) Uani 1.000000 .
C20 C -0.43952(12) -1.3141(3) -0.51135(14) 0.0304(6) Uani 1.000000 .
C21 C -0.40037(13) -1.4336(3) -0.49136(16) 0.0362(6) Uani 1.000000 .
C22 C -0.36165(12) -1.4324(2) -0.41766(17) 0.0358(6) Uani 1.000000 .
C23 C -0.36276(13) -1.3112(3) -0.36678(16) 0.0356(6) Uani 1.000000 .
C24 C -0.40322(12) -1.1937(2) -0.38976(15) 0.0320(6) Uani 1.000000 .
C25 C -0.52405(11) -0.9607(2) -0.41109(14) 0.0265(5) Uani 1.000000 .
C26 C -0.49291(12) -0.8385(3) -0.37618(14) 0.0295(5) Uani 1.000000 .
C27 C -0.51963(13) -0.7567(3) -0.31046(15) 0.0356(6) Uani 1.000000 .
C28 C -0.58224(13) -0.7963(3) -0.27680(15) 0.0417(7) Uani 1.000000 .
C29 C -0.61565(12) -0.9151(3) -0.30810(15) 0.0386(6) Uani 1.000000 .
C30 C -0.58636(12) -0.9946(3) -0.37284(14) 0.0310(6) Uani 1.000000 .
B1 B -0.49462(13) -1.0554(3) -0.49213(17) 0.0277(6) Uani 1.000000 .
H1c H -0.53548(13) -1.1023(3) -0.51942(17) 0.0333(7) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.9300 . ?
N1 C3 1.531(3) . ?
N1 C6 1.527(3) . ?
N1 C7 1.517(3) . ?
C1 H1a 0.9900 . ?
C1 H1b 0.9900 . ?
C1 C2 1.546(3) . ?
C1 C6 1.529(3) . ?
C2 H2a 0.9900 . ?
C2 H2b 0.9900 . ?
C2 C3 1.517(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.535(3) . ?
C4 H4a 0.9900 . ?
C4 H4b 0.9900 . ?
C4 C5 1.543(4) . ?
C5 H5a 0.9900 . ?
C5 H5b 0.9900 . ?
C5 C6 1.522(3) . ?
C6 H6 1.0000 . ?
C7 H7 1.0000 . ?
C7 C8 1.526(3) . ?
C7 C12 1.515(3) . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C9 1.522(3) . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C9 C10 1.521(3) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C10 C11 1.524(4) . ?
C11 H11a 0.9900 . ?
C11 H11b 0.9900 . ?
C11 C12 1.529(3) . ?
C12 H12a 0.9900 . ?
C12 H12b 0.9900 . ?
F1 C14 1.371(2) . ?
F2 C15 1.351(3) . ?
F3 C16 1.340(3) . ?
F4 C17 1.352(3) . ?
F5 C18 1.361(2) . ?
F6 C20 1.357(3) . ?
F7 C21 1.344(3) . ?
F8 C22 1.348(3) . ?
F9 C23 1.346(3) . ?
F10 C24 1.355(3) . ?
F11 C26 1.363(3) . ?
F12 C27 1.343(3) . ?
F13 C28 1.349(3) . ?
F14 C29 1.351(3) . ?
F15 C30 1.358(3) . ?
C13 C14 1.383(3) . ?
C13 C18 1.382(3) . ?
C13 B1 1.642(3) . ?
C14 C15 1.367(3) . ?
C15 C16 1.375(3) . ?
C16 C17 1.374(4) . ?
C17 C18 1.381(3) . ?
C19 C20 1.389(3) . ?
C19 C24 1.386(3) . ?
C19 B1 1.637(3) . ?
C20 C21 1.372(3) . ?
C21 C22 1.378(4) . ?
C22 C23 1.369(3) . ?
C23 C24 1.383(3) . ?
C25 C26 1.387(3) . ?
C25 C30 1.388(3) . ?
C25 B1 1.642(3) . ?
C26 C27 1.376(3) . ?
C27 C28 1.376(4) . ?
C28 C29 1.361(4) . ?
C29 C30 1.373(3) . ?
B1 H1c 1.0000 . ?

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
C3 N1 H1 108.31(10) . . ?
C6 N1 H1 108.31(11) . . ?
C6 N1 C3 94.72(16) . . ?
C7 N1 H1 108.31(10) . . ?
C7 N1 C3 120.31(16) . . ?
C7 N1 C6 115.84(17) . . ?
H1b C1 H1a 109.0 . . ?
C2 C1 H1a 111.08(12) . . ?
C2 C1 H1b 111.08(14) . . ?
C6 C1 H1a 111.08(12) . . ?
C6 C1 H1b 111.08(14) . . ?
C6 C1 C2 103.41(18) . . ?
H2a C2 C1 111.10(14) . . ?
H2b C2 C1 111.10(12) . . ?
H2b C2 H2a 109.1 . . ?
C3 C2 C1 103.31(18) . . ?
C3 C2 H2a 111.10(12) . . ?
C3 C2 H2b 111.10(12) . . ?
C2 C3 N1 101.27(17) . . ?
H3 C3 N1 114.63(11) . . ?
H3 C3 C2 114.63(12) . . ?
C4 C3 N1 99.58(17) . . ?
C4 C3 C2 110.36(19) . . ?
C4 C3 H3 114.63(12) . . ?
H4a C4 C3 111.02(13) . . ?
H4b C4 C3 111.02(12) . . ?
H4b C4 H4a 109.0 . . ?
C5 C4 C3 103.72(18) . . ?
C5 C4 H4a 111.02(14) . . ?
C5 C4 H4b 111.02(13) . . ?
H5a C5 C4 111.16(14) . . ?
H5b C5 C4 111.16(13) . . ?
H5b C5 H5a 109.1 . . ?
C6 C5 C4 103.03(18) . . ?
C6 C5 H5a 111.16(13) . . ?
C6 C5 H5b 111.16(12) . . ?
C1 C6 N1 101.31(17) . . ?
C5 C6 N1 100.04(18) . . ?
C5 C6 C1 110.4(2) . . ?
H6 C6 N1 114.47(11) . . ?
H6 C6 C1 114.47(13) . . ?
H6 C6 C5 114.47(13) . . ?
H7 C7 N1 108.66(10) . . ?
C8 C7 N1 107.46(16) . . ?
C8 C7 H7 108.66(12) . . ?
C12 C7 N1 111.71(17) . . ?
C12 C7 H7 108.66(12) . . ?
C12 C7 C8 111.61(18) . . ?
H8a C8 C7 109.52(12) . . ?
H8b C8 C7 109.52(12) . . ?
H8b C8 H8a 108.1 . . ?
C9 C8 C7 110.64(18) . . ?
C9 C8 H8a 109.52(13) . . ?
C9 C8 H8b 109.52(12) . . ?
H9a C9 C8 109.47(12) . . ?
H9b C9 C8 109.47(13) . . ?
H9b C9 H9a 108.1 . . ?
C10 C9 C8 110.87(19) . . ?
C10 C9 H9a 109.47(13) . . ?
C10 C9 H9b 109.47(13) . . ?
H10a C10 C9 109.50(13) . . ?
H10b C10 C9 109.50(13) . . ?
H10b C10 H10a 108.1 . . ?
C11 C10 C9 110.7(2) . . ?
C11 C10 H10a 109.50(14) . . ?
C11 C10 H10b 109.50(12) . . ?
H11a C11 C10 109.25(13) . . ?
H11b C11 C10 109.25(14) . . ?
H11b C11 H11a 107.9 . . ?
C12 C11 C10 111.81(19) . . ?
C12 C11 H11a 109.25(12) . . ?
C12 C11 H11b 109.25(13) . . ?
C11 C12 C7 109.55(18) . . ?
H12a C12 C7 109.76(12) . . ?
H12a C12 C11 109.76(13) . . ?
H12b C12 C7 109.76(12) . . ?
H12b C12 C11 109.76(13) . . ?
H12b C12 H12a 108.2 . . ?
C18 C13 C14 112.4(2) . . ?
B1 C13 C14 126.46(19) . . ?
B1 C13 C18 121.1(2) . . ?
C13 C14 F1 119.41(19) . . ?
C15 C14 F1 115.07(19) . . ?
C15 C14 C13 125.5(2) . . ?
C14 C15 F2 120.9(2) . . ?
C16 C15 F2 119.7(2) . . ?
C16 C15 C14 119.4(2) . . ?
C15 C16 F3 120.3(2) . . ?
C17 C16 F3 121.2(2) . . ?
C17 C16 C15 118.4(2) . . ?
C16 C17 F4 119.8(2) . . ?
C18 C17 F4 120.7(2) . . ?
C18 C17 C16 119.5(2) . . ?
C13 C18 F5 119.5(2) . . ?
C17 C18 F5 115.7(2) . . ?
C17 C18 C13 124.7(2) . . ?
C24 C19 C20 112.9(2) . . ?
B1 C19 C20 119.9(2) . . ?
B1 C19 C24 127.2(2) . . ?
C19 C20 F6 118.7(2) . . ?
C21 C20 F6 116.4(2) . . ?
C21 C20 C19 124.9(2) . . ?
C20 C21 F7 121.3(2) . . ?
C22 C21 F7 119.4(2) . . ?
C22 C21 C20 119.2(2) . . ?
C21 C22 F8 120.5(2) . . ?
C23 C22 F8 120.4(2) . . ?
C23 C22 C21 119.1(2) . . ?
C22 C23 F9 119.5(2) . . ?
C24 C23 F9 121.0(2) . . ?
C24 C23 C22 119.4(2) . . ?
C19 C24 F10 120.0(2) . . ?
C23 C24 F10 115.5(2) . . ?
C23 C24 C19 124.5(2) . . ?
C30 C25 C26 113.1(2) . . ?
B1 C25 C26 125.5(2) . . ?
B1 C25 C30 121.3(2) . . ?
C25 C26 F11 119.15(19) . . ?
C27 C26 F11 116.0(2) . . ?
C27 C26 C25 124.8(2) . . ?
C26 C27 F12 120.7(2) . . ?
C28 C27 F12 120.8(2) . . ?
C28 C27 C26 118.5(2) . . ?
C27 C28 F13 120.8(3) . . ?
C29 C28 F13 119.4(2) . . ?
C29 C28 C27 119.8(2) . . ?
C28 C29 F14 119.7(2) . . ?
C30 C29 F14 120.8(2) . . ?
C30 C29 C28 119.5(2) . . ?
C25 C30 F15 120.1(2) . . ?
C29 C30 F15 115.7(2) . . ?
C29 C30 C25 124.2(2) . . ?
C19 B1 C13 113.70(19) . . ?
C25 B1 C13 110.98(17) . . ?
C25 B1 C19 112.62(19) . . ?
H1c B1 C13 106.31(11) . . ?
H1c B1 C19 106.31(12) . . ?
H1c B1 C25 106.31(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tm077_0ma
_database_code_depnum_ccdc_archive 'CCDC 1046633'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;
_audit_creation_date             2015-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C15 H24 N O, C18 H B F15'
_chemical_formula_sum            'C33 H25 B F15 N O'
_chemical_formula_weight         747.37
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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

_symmetry_Int_Tables_number      61
_cell_length_a                   17.3531(15)
_cell_length_b                   16.1365(15)
_cell_length_c                   22.7522(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6371.0(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9369
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.35
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0603 before and 0.0416 after correction.
The Ratio of minimum to maximum transmission is 0.9653.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.5582
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             3026.8607
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            56289
_diffrn_reflns_theta_full        27.5376
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         1.79
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                5268
_reflns_number_total             7321
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.8255
_refine_diff_density_min         -0.4131
_refine_diff_density_rms         0.0683
_refine_ls_d_res_high            0.7686
_refine_ls_d_res_low             11.3761
_refine_ls_goodness_of_fit_ref   1.0647
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     461
_refine_ls_number_reflns         7321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.0647
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+3.4263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1112
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C24(H24), C30(H30), B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1a,H1b), C19(H19a,H19b), C20(H20a,H20b), C21(H21a,H21b), C34(H34a,H34b)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C28(H28), C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C29(H29a,H29b,H29c), C31(H31a,H31b,H31c)
;
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
O1 O 0.01176(8) 0.12596(9) 0.17746(7) 0.0456(4) Uani 1.000000 .
N1 N 0.00677(8) 0.27620(9) 0.12959(7) 0.0287(3) Uani 1.000000 .
H1a H 0.00087(8) 0.25805(9) 0.16766(7) 0.0345(4) Uiso 1.000000 R
H1b H 0.05507(8) 0.29939(9) 0.12689(7) 0.0345(4) Uiso 1.000000 R
C19 C 0.08252(11) 0.06952(13) 0.02571(10) 0.0428(5) Uani 1.000000 .
H19a H 0.07990(11) 0.01826(13) 0.00188(10) 0.0514(6) Uiso 1.000000 R
H19b H 0.13752(11) 0.08410(13) 0.03089(10) 0.0514(6) Uiso 1.000000 R
C20 C 0.04173(11) 0.13936(13) -0.00690(10) 0.0406(5) Uani 1.000000 .
H20a H 0.06892(11) 0.15042(13) -0.04435(10) 0.0488(6) Uiso 1.000000 R
H20b H -0.01156(11) 0.12202(13) -0.01639(10) 0.0488(6) Uiso 1.000000 R
C21 C 0.03940(11) 0.21898(12) 0.02987(8) 0.0332(4) Uani 1.000000 .
H21a H 0.09223(11) 0.24121(12) 0.03445(8) 0.0398(5) Uiso 1.000000 R
H21b H 0.00784(11) 0.26126(12) 0.00950(8) 0.0398(5) Uiso 1.000000 R
C22 C 0.00515(10) 0.20102(11) 0.09000(8) 0.0293(4) Uani 1.000000 .
H22 H -0.04961(10) 0.18319(11) 0.08477(8) 0.0351(5) Uiso 1.000000 R
C24 C -0.05128(10) 0.34398(12) 0.11928(8) 0.0303(4) Uani 1.000000 .
H24 H -0.04296(10) 0.36726(12) 0.07904(8) 0.0364(5) Uiso 1.000000 R
C25 C -0.13314(10) 0.31093(11) 0.12308(8) 0.0294(4) Uani 1.000000 .
C26 C -0.18081(11) 0.32065(14) 0.07525(9) 0.0393(5) Uani 1.000000 .
H26 H -0.16110(11) 0.34393(14) 0.03997(9) 0.0471(6) Uiso 1.000000 R
C27 C -0.25740(12) 0.29670(16) 0.07823(10) 0.0490(6) Uani 1.000000 .
H27 H -0.28986(12) 0.30407(16) 0.04502(10) 0.0589(7) Uiso 1.000000 R
C28 C -0.28667(12) 0.26263(15) 0.12842(11) 0.0484(6) Uani 1.000000 .
H28 H -0.33940(12) 0.24701(15) 0.13035(11) 0.0581(7) Uiso 1.000000 R
C29 C 0.05217(18) 0.07722(19) 0.21915(12) 0.0724(9) Uani 1.000000 .
H29a H 0.0578(11) 0.0206(4) 0.2041(4) 0.1086(13) Uiso 1.000000 GR
H29b H 0.1033(5) 0.1013(8) 0.2259(7) 0.1086(13) Uiso 1.000000 GR
H29c H 0.0234(7) 0.0761(11) 0.2562(3) 0.1086(13) Uiso 1.000000 GR
C30 C 0.04871(10) 0.13253(11) 0.12202(9) 0.0334(4) Uani 1.000000 .
H30 H 0.10347(10) 0.14994(11) 0.12790(9) 0.0401(5) Uiso 1.000000 R
C31 C -0.03575(11) 0.41234(12) 0.16453(9) 0.0335(4) Uani 1.000000 .
H31a H -0.0414(8) 0.3897(2) 0.20426(9) 0.0502(6) Uiso 1.000000 GR
H31b H 0.0168(3) 0.4335(6) 0.1593(4) 0.0502(6) Uiso 1.000000 GR
H31c H -0.0727(5) 0.4576(4) 0.1589(4) 0.0502(6) Uiso 1.000000 GR
C32 C -0.23936(13) 0.25110(15) 0.17605(11) 0.0512(6) Uani 1.000000 .
H32 H -0.25904(13) 0.22636(15) 0.21084(11) 0.0615(7) Uiso 1.000000 R
C33 C -0.16287(12) 0.27556(14) 0.17340(10) 0.0441(5) Uani 1.000000 .
H33 H -0.13053(12) 0.26788(14) 0.20665(10) 0.0529(6) Uiso 1.000000 R
C34 C 0.04658(11) 0.05361(12) 0.08538(10) 0.0426(5) Uani 1.000000 .
H34a H -0.00744(11) 0.03518(12) 0.08037(10) 0.0511(6) Uiso 1.000000 R
H34b H 0.07525(11) 0.00910(12) 0.10584(10) 0.0511(6) Uiso 1.000000 R
F1 F 0.15605(9) 0.57430(10) 0.30088(6) 0.0622(4) Uani 1.000000 .
F2 F 0.49840(8) 0.13334(9) 0.13999(7) 0.0659(4) Uani 1.000000 .
F3 F 0.48626(7) 0.27510(9) 0.20417(7) 0.0641(4) Uani 1.000000 .
F4 F 0.36398(6) 0.37283(7) 0.19362(5) 0.0444(3) Uani 1.000000 .
F5 F 0.27988(7) 0.50989(7) 0.12488(5) 0.0431(3) Uani 1.000000 .
F6 F 0.24767(9) 0.61836(7) 0.20964(5) 0.0523(3) Uani 1.000000 .
F7 F 0.09848(8) 0.41699(10) 0.30719(5) 0.0609(4) Uani 1.000000 .
F8 F 0.12941(7) 0.30745(8) 0.22255(5) 0.0423(3) Uani 1.000000 .
F9 F 0.08913(5) 0.40967(7) 0.06312(5) 0.0325(2) Uani 1.000000 .
F10 F 0.07597(6) 0.47440(8) -0.04426(5) 0.0429(3) Uani 1.000000 .
F11 F 0.20058(7) 0.47917(8) -0.11791(5) 0.0462(3) Uani 1.000000 .
F12 F 0.33939(6) 0.42199(8) -0.07860(5) 0.0428(3) Uani 1.000000 .
F13 F 0.35389(6) 0.35887(8) 0.02749(5) 0.0407(3) Uani 1.000000 .
F14 F 0.25300(7) 0.18022(7) 0.06145(5) 0.0438(3) Uani 1.000000 .
F15 F 0.37976(9) 0.08710(8) 0.06869(6) 0.0580(4) Uani 1.000000 .
C1 C 0.17229(12) 0.51888(14) 0.25912(8) 0.0389(5) Uani 1.000000 .
C2 C 0.21789(12) 0.54111(12) 0.21232(8) 0.0364(4) Uani 1.000000 .
C3 C 0.23333(10) 0.48389(12) 0.16892(8) 0.0307(4) Uani 1.000000 .
C4 C 0.20572(9) 0.40341(11) 0.16878(7) 0.0260(4) Uani 1.000000 .
C5 C 0.30074(10) 0.28117(11) 0.12744(7) 0.0250(4) Uani 1.000000 .
C6 C 0.36310(11) 0.30111(11) 0.16252(8) 0.0309(4) Uani 1.000000 .
C7 C 0.42825(11) 0.25256(14) 0.16805(9) 0.0401(5) Uani 1.000000 .
C8 C 0.43449(12) 0.18038(13) 0.13627(9) 0.0412(5) Uani 1.000000 .
C9 C 0.14352(11) 0.43978(15) 0.26187(8) 0.0390(5) Uani 1.000000 .
C10 C 0.16084(10) 0.38442(12) 0.21725(8) 0.0304(4) Uani 1.000000 .
C11 C 0.22179(9) 0.37929(10) 0.05121(7) 0.0234(3) Uani 1.000000 .
C12 C 0.15346(9) 0.41094(11) 0.02892(7) 0.0245(4) Uani 1.000000 .
C13 C 0.14455(10) 0.44457(11) -0.02636(8) 0.0295(4) Uani 1.000000 .
C14 C 0.20748(11) 0.44810(12) -0.06330(8) 0.0306(4) Uani 1.000000 .
C15 C 0.27701(10) 0.41871(12) -0.04344(8) 0.0288(4) Uani 1.000000 .
C16 C 0.28262(9) 0.38592(11) 0.01224(8) 0.0269(4) Uani 1.000000 .
C17 C 0.31009(11) 0.20666(11) 0.09753(8) 0.0301(4) Uani 1.000000 .
C18 C 0.37434(12) 0.15748(12) 0.10060(9) 0.0365(4) Uani 1.000000 .
B1 B 0.22285(11) 0.33596(13) 0.11677(8) 0.0246(4) Uani 1.000000 .
H1 H 0.17886(11) 0.29594(13) 0.11745(8) 0.0296(5) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C29 1.418(3) . ?
O1 C30 1.419(2) . ?
N1 H1a 0.9200 . ?
N1 H1b 0.9200 . ?
N1 C22 1.511(2) . ?
N1 C24 1.505(2) . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
C19 C20 1.524(3) . ?
C19 C34 1.516(3) . ?
C20 H20a 0.9900 . ?
C20 H20b 0.9900 . ?
C20 C21 1.534(3) . ?
C21 H21a 0.9900 . ?
C21 H21b 0.9900 . ?
C21 C22 1.519(3) . ?
C22 H22 1.0000 . ?
C22 C30 1.524(3) . ?
C24 H24 1.0000 . ?
C24 C25 1.520(2) . ?
C24 C31 1.533(3) . ?
C25 C26 1.376(3) . ?
C25 C33 1.380(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.386(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.365(3) . ?
C28 H28 0.9500 . ?
C28 C32 1.372(3) . ?
C29 H29a 0.9800 . ?
C29 H29b 0.9800 . ?
C29 H29c 0.9800 . ?
C30 H30 1.0000 . ?
C30 C34 1.523(3) . ?
C31 H31a 0.9800 . ?
C31 H31b 0.9800 . ?
C31 H31c 0.9800 . ?
C32 H32 0.9500 . ?
C32 C33 1.386(3) . ?
C33 H33 0.9500 . ?
C34 H34a 0.9900 . ?
C34 H34b 0.9900 . ?
F1 C1 1.335(2) . ?
F2 C8 1.347(2) . ?
F3 C7 1.349(2) . ?
F4 C6 1.357(2) . ?
F5 C3 1.354(2) . ?
F6 C2 1.351(2) . ?
F7 C9 1.345(2) . ?
F8 C10 1.362(2) . ?
F9 C12 1.3609(18) . ?
F10 C13 1.347(2) . ?
F11 C14 1.345(2) . ?
F12 C15 1.347(2) . ?
F13 C16 1.3567(19) . ?
F14 C17 1.355(2) . ?
F15 C18 1.351(2) . ?
C1 C2 1.374(3) . ?
C1 C9 1.372(3) . ?
C2 C3 1.378(3) . ?
C3 C4 1.384(3) . ?
C4 C10 1.384(2) . ?
C4 B1 1.635(3) . ?
C5 C6 1.383(2) . ?
C5 C17 1.391(2) . ?
C5 B1 1.633(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.375(3) . ?
C8 C18 1.373(3) . ?
C9 C10 1.385(3) . ?
C11 C12 1.387(2) . ?
C11 C16 1.383(2) . ?
C11 B1 1.647(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.373(3) . ?
C15 C16 1.376(3) . ?
C17 C18 1.370(3) . ?
B1 H1 1.0000 . ?

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
C30 O1 C29 114.37(17) . . ?
H1b N1 H1a 107.1 . . ?
C22 N1 H1a 107.68(9) . . ?
C22 N1 H1b 107.68(9) . . ?
C24 N1 H1a 107.68(9) . . ?
C24 N1 H1b 107.68(9) . . ?
C24 N1 C22 118.54(14) . . ?
H19b C19 H19a 107.9 . . ?
C20 C19 H19a 109.27(10) . . ?
C20 C19 H19b 109.27(11) . . ?
C34 C19 H19a 109.27(11) . . ?
C34 C19 H19b 109.27(11) . . ?
C34 C19 C20 111.73(17) . . ?
H20a C20 C19 109.33(11) . . ?
H20b C20 C19 109.33(11) . . ?
H20b C20 H20a 108.0 . . ?
C21 C20 C19 111.48(16) . . ?
C21 C20 H20a 109.33(11) . . ?
C21 C20 H20b 109.33(10) . . ?
H21a C21 C20 109.67(10) . . ?
H21b C21 C20 109.67(11) . . ?
H21b C21 H21a 108.2 . . ?
C22 C21 C20 109.98(16) . . ?
C22 C21 H21a 109.67(9) . . ?
C22 C21 H21b 109.67(10) . . ?
C21 C22 N1 112.11(15) . . ?
H22 C22 N1 108.63(8) . . ?
H22 C22 C21 108.63(10) . . ?
C30 C22 N1 106.73(14) . . ?
C30 C22 C21 112.01(15) . . ?
C30 C22 H22 108.63(9) . . ?
H24 C24 N1 108.60(9) . . ?
C25 C24 N1 111.20(15) . . ?
C25 C24 H24 108.60(10) . . ?
C31 C24 N1 107.48(14) . . ?
C31 C24 H24 108.60(10) . . ?
C31 C24 C25 112.26(15) . . ?
C26 C25 C24 118.49(17) . . ?
C33 C25 C24 122.82(17) . . ?
C33 C25 C26 118.60(18) . . ?
H26 C26 C25 119.80(11) . . ?
C27 C26 C25 120.41(19) . . ?
C27 C26 H26 119.80(13) . . ?
H27 C27 C26 119.67(13) . . ?
C28 C27 C26 120.7(2) . . ?
C28 C27 H27 119.67(13) . . ?
H28 C28 C27 120.25(13) . . ?
C32 C28 C27 119.50(19) . . ?
C32 C28 H28 120.25(12) . . ?
H29a C29 O1 109.5 . . ?
H29b C29 O1 109.5 . . ?
H29b C29 H29a 109.5 . . ?
H29c C29 O1 109.5 . . ?
H29c C29 H29a 109.5 . . ?
H29c C29 H29b 109.5 . . ?
C22 C30 O1 104.77(14) . . ?
H30 C30 O1 109.36(10) . . ?
H30 C30 C22 109.36(9) . . ?
C34 C30 O1 114.41(16) . . ?
C34 C30 C22 109.43(16) . . ?
C34 C30 H30 109.36(10) . . ?
H31a C31 C24 109.5 . . ?
H31b C31 C24 109.5 . . ?
H31b C31 H31a 109.5 . . ?
H31c C31 C24 109.5 . . ?
H31c C31 H31a 109.5 . . ?
H31c C31 H31b 109.5 . . ?
H32 C32 C28 120.00(12) . . ?
C33 C32 C28 120.0(2) . . ?
C33 C32 H32 120.00(13) . . ?
C32 C33 C25 120.8(2) . . ?
H33 C33 C25 119.60(12) . . ?
H33 C33 C32 119.60(13) . . ?
C30 C34 C19 109.80(17) . . ?
H34a C34 C19 109.71(11) . . ?
H34a C34 C30 109.71(10) . . ?
H34b C34 C19 109.71(11) . . ?
H34b C34 C30 109.71(11) . . ?
H34b C34 H34a 108.2 . . ?
C2 C1 F1 119.9(2) . . ?
C9 C1 F1 120.93(19) . . ?
C9 C1 C2 119.19(18) . . ?
C1 C2 F6 119.74(18) . . ?
C3 C2 F6 120.77(18) . . ?
C3 C2 C1 119.49(19) . . ?
C2 C3 F5 116.02(17) . . ?
C4 C3 F5 119.71(16) . . ?
C4 C3 C2 124.25(17) . . ?
C10 C4 C3 113.62(16) . . ?
B1 C4 C3 124.28(15) . . ?
B1 C4 C10 122.10(16) . . ?
C17 C5 C6 113.10(16) . . ?
B1 C5 C6 127.41(16) . . ?
B1 C5 C17 119.45(15) . . ?
C5 C6 F4 120.56(16) . . ?
C7 C6 F4 115.28(16) . . ?
C7 C6 C5 124.15(17) . . ?
C6 C7 F3 120.88(18) . . ?
C8 C7 F3 119.33(18) . . ?
C8 C7 C6 119.79(18) . . ?
C7 C8 F2 120.61(19) . . ?
C18 C8 F2 120.78(18) . . ?
C18 C8 C7 118.62(18) . . ?
C1 C9 F7 120.05(19) . . ?
C10 C9 F7 120.8(2) . . ?
C10 C9 C1 119.18(18) . . ?
C4 C10 F8 119.85(17) . . ?
C9 C10 F8 115.87(16) . . ?
C9 C10 C4 124.27(19) . . ?
C16 C11 C12 112.92(15) . . ?
B1 C11 C12 119.80(14) . . ?
B1 C11 C16 127.22(15) . . ?
C11 C12 F9 119.12(15) . . ?
C13 C12 F9 115.82(15) . . ?
C13 C12 C11 125.06(16) . . ?
C12 C13 F10 121.04(16) . . ?
C14 C13 F10 120.04(16) . . ?
C14 C13 C12 118.92(16) . . ?
C13 C14 F11 120.53(16) . . ?
C15 C14 F11 120.73(16) . . ?
C15 C14 C13 118.74(16) . . ?
C14 C15 F12 119.81(16) . . ?
C16 C15 F12 120.32(16) . . ?
C16 C15 C14 119.86(16) . . ?
C11 C16 F13 120.46(15) . . ?
C15 C16 F13 115.06(15) . . ?
C15 C16 C11 124.47(16) . . ?
C5 C17 F14 118.89(16) . . ?
C18 C17 F14 116.31(16) . . ?
C18 C17 C5 124.79(17) . . ?
C8 C18 F15 119.40(18) . . ?
C17 C18 F15 121.07(18) . . ?
C17 C18 C8 119.53(17) . . ?
C5 B1 C4 113.78(14) . . ?
C11 B1 C4 111.76(14) . . ?
C11 B1 C5 111.94(14) . . ?
H1 B1 C4 106.25(9) . . ?
H1 B1 C5 106.25(9) . . ?
H1 B1 C11 106.25(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
