# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_i14557
_database_code_depnum_ccdc_archive 'CCDC 953115'
_audit_update_record             
;
2013-07-30 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H22 B2 F4 N4 O2'
_chemical_formula_sum            'C32 H22 B2 F4 N4 O2'
_chemical_formula_weight         592.16

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9566(4)
_cell_length_b                   8.3315(5)
_cell_length_c                   23.1202(12)
_cell_angle_alpha                95.844(2)
_cell_angle_beta                 90.570(2)
_cell_angle_gamma                96.433(2)
_cell_volume                     1324.35(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    9707
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      29.87

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_T_max  0.9888

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_number            20395
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         0.89
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             5429
_reflns_number_gt                4220
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0372P)²+0.4504P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0038(7)
_refine_ls_number_reflns         5429
_refine_ls_number_parameters     398
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.01
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.24815(11) 0.57226(10) 0.94596(3) 0.0218(2) Uani 1 1 d U . .
F2 F 0.34887(11) 0.84035(10) 0.96996(4) 0.0228(2) Uani 1 1 d U . .
O1 O 0.07548(14) 0.76221(13) 0.91034(4) 0.0227(2) Uani 1 1 d U . .
B1 B 0.1895(2) 0.72441(19) 0.95923(7) 0.0172(3) Uani 1 1 d U . .
C1 C -0.09358(19) 0.82208(16) 0.91431(6) 0.0173(3) Uani 1 1 d U . .
C2 C -0.18227(19) 0.84091(16) 0.96618(6) 0.0169(3) Uani 1 1 d U . .
H2 H -0.3003 0.8884 0.9683 0.02 Uiso 1 1 calc R . .
C3 C -0.10301(18) 0.79146(16) 1.01725(6) 0.0151(3) Uani 1 1 d U . .
C4 C -0.20492(19) 0.80925(17) 1.07105(6) 0.0172(3) Uani 1 1 d U . .
H4 H -0.3229 0.8566 1.0708 0.021 Uiso 1 1 calc R . .
C5 C 0.02503(19) 0.69547(17) 1.11890(6) 0.0178(3) Uani 1 1 d U . .
C6 C 0.0891(2) 0.64012(19) 1.17024(6) 0.0232(3) Uani 1 1 d U . .
H6 H 0.0148 0.6516 1.2044 0.028 Uiso 1 1 calc R . .
C7 C 0.2574(2) 0.56982(19) 1.17172(6) 0.0234(3) Uani 1 1 d U . .
H7 H 0.2982 0.5306 1.2065 0.028 Uiso 1 1 calc R . .
C8 C 0.3693(2) 0.55595(18) 1.12172(6) 0.0213(3) Uani 1 1 d U . .
H8 H 0.4875 0.5091 1.1232 0.026 Uiso 1 1 calc R . .
C9 C 0.3110(2) 0.60893(17) 1.07071(6) 0.0191(3) Uani 1 1 d U . .
H9 H 0.389 0.5995 1.0373 0.023 Uiso 1 1 calc R . .
C10 C 0.13518(19) 0.67733(16) 1.06815(6) 0.0157(3) Uani 1 1 d U . .
C11 C -0.1741(2) 0.86197(17) 0.85880(6) 0.0191(3) Uani 1 1 d U . .
C12 C -0.3596(2) 0.9107(2) 0.85579(7) 0.0263(3) Uani 1 1 d U . .
H12 H -0.4349 0.9188 0.8898 0.032 Uiso 1 1 calc R . .
C13 C -0.4340(2) 0.9472(2) 0.80349(7) 0.0316(4) Uani 1 1 d U . .
H13 H -0.5599 0.9809 0.8019 0.038 Uiso 1 1 calc R . .
C14 C -0.3261(2) 0.9349(2) 0.75368(7) 0.0296(4) Uani 1 1 d U . .
H4 H -0.3782 0.9591 0.7178 0.036 Uiso 1 1 calc R . .
C15 C -0.1421(2) 0.8872(2) 0.75609(7) 0.0286(4) Uani 1 1 d U . .
H15 H -0.0676 0.8792 0.7219 0.034 Uiso 1 1 calc R . .
C16 C -0.0663(2) 0.85099(18) 0.80836(6) 0.0234(3) Uani 1 1 d U . .
H16 H 0.0601 0.8185 0.8098 0.028 Uiso 1 1 calc R . .
F3 F 0.07619(12) 0.90730(10) 0.62521(4) 0.0242(2) Uani 1 1 d U . .
F4 F 0.39975(12) 0.88829(10) 0.62178(4) 0.0241(2) Uani 1 1 d U . .
O2 O 0.21163(15) 0.83898(12) 0.53661(4) 0.0211(2) Uani 1 1 d U . .
N1 N 0.06626(15) 0.72818(13) 1.01680(5) 0.0147(2) Uani 1 1 d U . .
N2 N -0.14640(16) 0.76496(14) 1.11975(5) 0.0187(3) Uani 1 1 d U . .
N3 N 0.28450(16) 1.12201(14) 0.58559(5) 0.0158(2) Uani 1 1 d U . .
N4 N 0.37943(17) 1.45180(15) 0.56930(5) 0.0207(3) Uani 1 1 d U . .
B2 B 0.2418(2) 0.9338(2) 0.59320(7) 0.0183(3) Uani 1 1 d U . .
C17 C 0.22618(19) 0.89695(17) 0.48527(6) 0.0166(3) Uani 1 1 d U . .
C18 C 0.27052(19) 1.05832(17) 0.48156(6) 0.0178(3) Uani 1 1 d U . .
H18 H 0.2811 1.0969 0.4443 0.021 Uiso 1 1 calc R . .
C19 C 0.30138(19) 1.17033(17) 0.53185(6) 0.0167(3) Uani 1 1 d U . .
C20 C 0.3531(2) 1.33883(17) 0.52606(6) 0.0202(3) Uani 1 1 d U . .
H20 H 0.3694 1.3703 0.4879 0.024 Uiso 1 1 calc R . .
C21 C 0.35627(19) 1.40333(17) 0.62439(6) 0.0184(3) Uani 1 1 d U . .
C22 C 0.3805(2) 1.52282(18) 0.67223(6) 0.0214(3) Uani 1 1 d U . .
H22 H 0.4082 1.634 0.6661 0.026 Uiso 1 1 calc R . .
C23 C 0.3641(2) 1.47922(19) 0.72768(6) 0.0223(3) Uani 1 1 d U . .
H23 H 0.3785 1.5602 0.7599 0.027 Uiso 1 1 calc R . .
C24 C 0.3258(2) 1.31443(18) 0.73679(6) 0.0207(3) Uani 1 1 d U . .
H24 H 0.3185 1.285 0.7754 0.025 Uiso 1 1 calc R . .
C25 C 0.29881(19) 1.19542(18) 0.69094(6) 0.0191(3) Uani 1 1 d U . .
H25 H 0.2712 1.0848 0.6978 0.023 Uiso 1 1 calc R . .
C26 C 0.31226(19) 1.23810(17) 0.63359(6) 0.0167(3) Uani 1 1 d U . .
C27 C 0.19200(19) 0.77332(17) 0.43485(6) 0.0176(3) Uani 1 1 d U . .
C28 C 0.1391(2) 0.61093(18) 0.44369(6) 0.0217(3) Uani 1 1 d U . .
H28 H 0.1254 0.5811 0.4821 0.026 Uiso 1 1 calc R . .
C29 C 0.1063(2) 0.49298(19) 0.39669(7) 0.0252(3) Uani 1 1 d U . .
H29 H 0.069 0.383 0.403 0.03 Uiso 1 1 calc R . .
C30 C 0.1279(2) 0.5356(2) 0.34054(7) 0.0254(3) Uani 1 1 d U . .
H30 H 0.1062 0.4547 0.3084 0.03 Uiso 1 1 calc R . .
C31 C 0.1810(2) 0.69598(19) 0.33120(7) 0.0236(3) Uani 1 1 d U . .
H31 H 0.1961 0.7247 0.2927 0.028 Uiso 1 1 calc R . .
C32 C 0.2124(2) 0.81464(18) 0.37792(6) 0.0205(3) Uani 1 1 d U . .
H32 H 0.2478 0.9246 0.3712 0.025 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
F1 B1 1.3808(18) . ?
F2 B1 1.3889(18) . ?
O1 C1 1.3284(16) . ?
O1 B1 1.4549(19) . ?
B1 N1 1.5901(19) . ?
C1 C2 1.3571(19) . ?
C1 C11 1.478(2) . ?
C2 C3 1.4160(19) . ?
C2 H2 0.95 . ?
C3 N1 1.3427(17) . ?
C3 C4 1.4406(19) . ?
C4 N2 1.2956(18) . ?
C4 H4 0.95 . ?
C5 N2 1.3823(17) . ?
C5 C6 1.403(2) . ?
C5 C10 1.4122(19) . ?
C6 C7 1.368(2) . ?
C6 H6 0.95 . ?
C7 C8 1.402(2) . ?
C7 H7 0.95 . ?
C8 C9 1.374(2) . ?
C8 H8 0.95 . ?
C9 C10 1.4094(19) . ?
C9 H9 0.95 . ?
C10 N1 1.3983(17) . ?
C11 C16 1.394(2) . ?
C11 C12 1.398(2) . ?
C12 C13 1.386(2) . ?
C12 H12 0.95 . ?
C13 C14 1.382(2) . ?
C13 H13 0.95 . ?
C14 C15 1.384(2) . ?
C14 H4 0.95 . ?
C15 C16 1.388(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
F3 B2 1.3843(18) . ?
F4 B2 1.3848(18) . ?
O2 C17 1.3270(16) . ?
O2 B2 1.4583(19) . ?
N3 C19 1.3468(18) . ?
N3 C26 1.3928(18) . ?
N3 B2 1.591(2) . ?
N4 C20 1.2980(18) . ?
N4 C21 1.3804(18) . ?
C17 C18 1.357(2) . ?
C17 C27 1.474(2) . ?
C18 C19 1.413(2) . ?
C18 H18 0.95 . ?
C19 C20 1.430(2) . ?
C20 H20 0.95 . ?
C21 C22 1.406(2) . ?
C21 C26 1.414(2) . ?
C22 C23 1.370(2) . ?
C22 H22 0.95 . ?
C23 C24 1.407(2) . ?
C23 H23 0.95 . ?
C24 C25 1.372(2) . ?
C24 H24 0.95 . ?
C25 C26 1.409(2) . ?
C25 H25 0.95 . ?
C27 C32 1.399(2) . ?
C27 C28 1.398(2) . ?
C28 C29 1.388(2) . ?
C28 H28 0.95 . ?
C29 C30 1.386(2) . ?
C29 H29 0.95 . ?
C30 C31 1.385(2) . ?
C30 H30 0.95 . ?
C31 C32 1.386(2) . ?
C31 H31 0.95 . ?
C32 H32 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 B1 125.20(11) . . ?
F1 B1 F2 110.46(12) . . ?
F1 B1 O1 108.49(12) . . ?
F2 B1 O1 110.00(12) . . ?
F1 B1 N1 110.14(12) . . ?
F2 B1 N1 106.99(11) . . ?
O1 B1 N1 110.75(11) . . ?
O1 C1 C2 120.74(13) . . ?
O1 C1 C11 114.98(12) . . ?
C2 C1 C11 124.27(13) . . ?
C1 C2 C3 121.54(13) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
N1 C3 C2 121.39(12) . . ?
N1 C3 C4 118.91(12) . . ?
C2 C3 C4 119.70(12) . . ?
N2 C4 C3 124.37(13) . . ?
N2 C4 H4 117.8 . . ?
C3 C4 H4 117.8 . . ?
N2 C5 C6 118.35(13) . . ?
N2 C5 C10 122.16(13) . . ?
C6 C5 C10 119.50(13) . . ?
C7 C6 C5 120.72(14) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.71(14) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 121.11(13) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.73(13) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N1 C10 C9 121.97(12) . . ?
N1 C10 C5 118.85(12) . . ?
C9 C10 C5 119.18(13) . . ?
C16 C11 C12 118.76(14) . . ?
C16 C11 C1 120.43(13) . . ?
C12 C11 C1 120.81(13) . . ?
C13 C12 C11 120.37(14) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.31(15) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.90(15) . . ?
C13 C14 H4 120 . . ?
C15 C14 H4 120 . . ?
C14 C15 C16 120.11(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.55(15) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C17 O2 B2 126.03(12) . . ?
C3 N1 C10 118.97(11) . . ?
C3 N1 B1 119.12(11) . . ?
C10 N1 B1 121.78(11) . . ?
C4 N2 C5 116.71(12) . . ?
C19 N3 C26 119.04(12) . . ?
C19 N3 B2 119.66(11) . . ?
C26 N3 B2 121.26(11) . . ?
C20 N4 C21 116.78(13) . . ?
F3 B2 F4 110.53(12) . . ?
F3 B2 O2 108.57(12) . . ?
F4 B2 O2 109.94(12) . . ?
F3 B2 N3 109.50(12) . . ?
F4 B2 N3 107.89(12) . . ?
O2 B2 N3 110.41(11) . . ?
O2 C17 C18 120.76(13) . . ?
O2 C17 C27 114.73(12) . . ?
C18 C17 C27 124.51(13) . . ?
C17 C18 C19 121.50(13) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
N3 C19 C18 121.48(13) . . ?
N3 C19 C20 118.76(13) . . ?
C18 C19 C20 119.76(13) . . ?
N4 C20 C19 124.58(13) . . ?
N4 C20 H20 117.7 . . ?
C19 C20 H20 117.7 . . ?
N4 C21 C22 118.34(13) . . ?
N4 C21 C26 121.80(13) . . ?
C22 C21 C26 119.85(13) . . ?
C23 C22 C21 120.12(14) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.93(14) . . ?
C22 C23 H23 120 . . ?
C24 C23 H23 120 . . ?
C25 C24 C23 121.21(14) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 119.66(14) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
N3 C26 C25 121.86(13) . . ?
N3 C26 C21 118.96(12) . . ?
C25 C26 C21 119.18(13) . . ?
C32 C27 C28 118.90(13) . . ?
C32 C27 C17 121.37(13) . . ?
C28 C27 C17 119.72(13) . . ?
C29 C28 C27 120.46(14) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 120.00(15) . . ?
C30 C29 H29 120 . . ?
C28 C29 H29 120 . . ?
C29 C30 C31 120.11(14) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 120.21(14) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C27 120.32(14) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 B1 F1 133.10(13) . . . . ?
C1 O1 B1 F2 -105.97(14) . . . . ?
C1 O1 B1 N1 12.10(19) . . . . ?
B1 O1 C1 C2 -5.4(2) . . . . ?
B1 O1 C1 C11 175.54(13) . . . . ?
O1 C1 C2 C3 -2.7(2) . . . . ?
C11 C1 C2 C3 176.21(13) . . . . ?
C1 C2 C3 N1 2.0(2) . . . . ?
C1 C2 C3 C4 -178.14(13) . . . . ?
N1 C3 C4 N2 -1.5(2) . . . . ?
C2 C3 C4 N2 178.65(13) . . . . ?
N2 C5 C6 C7 179.74(13) . . . . ?
C10 C5 C6 C7 0.4(2) . . . . ?
C5 C6 C7 C8 1.4(2) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C8 C9 C10 N1 -177.86(13) . . . . ?
C8 C9 C10 C5 2.2(2) . . . . ?
N2 C5 C10 N1 -1.4(2) . . . . ?
C6 C5 C10 N1 177.91(12) . . . . ?
N2 C5 C10 C9 178.49(13) . . . . ?
C6 C5 C10 C9 -2.2(2) . . . . ?
O1 C1 C11 C16 -6.10(19) . . . . ?
C2 C1 C11 C16 174.90(14) . . . . ?
O1 C1 C11 C12 173.64(13) . . . . ?
C2 C1 C11 C12 -5.4(2) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
C1 C11 C12 C13 -179.73(15) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C11 0.1(2) . . . . ?
C12 C11 C16 C15 -0.2(2) . . . . ?
C1 C11 C16 C15 179.51(14) . . . . ?
C2 C3 N1 C10 -178.29(12) . . . . ?
C4 C3 N1 C10 1.84(18) . . . . ?
C2 C3 N1 B1 5.91(19) . . . . ?
C4 C3 N1 B1 -173.97(12) . . . . ?
C9 C10 N1 C3 179.60(12) . . . . ?
C5 C10 N1 C3 -0.50(18) . . . . ?
C9 C10 N1 B1 -4.71(19) . . . . ?
C5 C10 N1 B1 175.19(12) . . . . ?
F1 B1 N1 C3 -132.04(13) . . . . ?
F2 B1 N1 C3 107.86(13) . . . . ?
O1 B1 N1 C3 -12.03(17) . . . . ?
F1 B1 N1 C10 52.28(16) . . . . ?
F2 B1 N1 C10 -67.82(15) . . . . ?
O1 B1 N1 C10 172.29(11) . . . . ?
C3 C4 N2 C5 -0.4(2) . . . . ?
C6 C5 N2 C4 -177.52(13) . . . . ?
C10 C5 N2 C4 1.8(2) . . . . ?
C17 O2 B2 F3 123.15(14) . . . . ?
C17 O2 B2 F4 -115.83(14) . . . . ?
C17 O2 B2 N3 3.10(18) . . . . ?
C19 N3 B2 F3 -124.00(13) . . . . ?
C26 N3 B2 F3 58.48(16) . . . . ?
C19 N3 B2 F4 115.65(13) . . . . ?
C26 N3 B2 F4 -61.87(16) . . . . ?
C19 N3 B2 O2 -4.52(17) . . . . ?
C26 N3 B2 O2 177.96(11) . . . . ?
B2 O2 C17 C18 -0.8(2) . . . . ?
B2 O2 C17 C27 178.80(12) . . . . ?
O2 C17 C18 C19 -0.5(2) . . . . ?
C27 C17 C18 C19 179.96(12) . . . . ?
C26 N3 C19 C18 -178.57(12) . . . . ?
B2 N3 C19 C18 3.86(19) . . . . ?
C26 N3 C19 C20 1.89(18) . . . . ?
B2 N3 C19 C20 -175.68(12) . . . . ?
C17 C18 C19 N3 -1.3(2) . . . . ?
C17 C18 C19 C20 178.27(13) . . . . ?
C21 N4 C20 C19 0.4(2) . . . . ?
N3 C19 C20 N4 -2.4(2) . . . . ?
C18 C19 C20 N4 178.04(13) . . . . ?
C20 N4 C21 C22 -178.94(13) . . . . ?
C20 N4 C21 C26 2.0(2) . . . . ?
N4 C21 C22 C23 -178.16(13) . . . . ?
C26 C21 C22 C23 0.9(2) . . . . ?
C21 C22 C23 C24 0.9(2) . . . . ?
C22 C23 C24 C25 -1.9(2) . . . . ?
C23 C24 C25 C26 0.9(2) . . . . ?
C19 N3 C26 C25 -179.28(12) . . . . ?
B2 N3 C26 C25 -1.75(19) . . . . ?
C19 N3 C26 C21 0.35(18) . . . . ?
B2 N3 C26 C21 177.89(12) . . . . ?
C24 C25 C26 N3 -179.46(12) . . . . ?
C24 C25 C26 C21 0.9(2) . . . . ?
N4 C21 C26 N3 -2.4(2) . . . . ?
C22 C21 C26 N3 178.54(12) . . . . ?
N4 C21 C26 C25 177.21(12) . . . . ?
C22 C21 C26 C25 -1.8(2) . . . . ?
O2 C17 C27 C32 -176.55(12) . . . . ?
C18 C17 C27 C32 3.1(2) . . . . ?
O2 C17 C27 C28 3.11(18) . . . . ?
C18 C17 C27 C28 -177.28(13) . . . . ?
C32 C27 C28 C29 -0.4(2) . . . . ?
C17 C27 C28 C29 179.98(13) . . . . ?
C27 C28 C29 C30 0.7(2) . . . . ?
C28 C29 C30 C31 -0.4(2) . . . . ?
C29 C30 C31 C32 -0.2(2) . . . . ?
C30 C31 C32 C27 0.5(2) . . . . ?
C28 C27 C32 C31 -0.2(2) . . . . ?
C17 C27 C32 C31 179.44(12) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_i14573
_database_code_depnum_ccdc_archive 'CCDC 953117'
_audit_update_record             
;
2013-07-30 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H13 B F2 N2 O'
_chemical_formula_sum            'C17 H13 B F2 N2 O'
_chemical_formula_weight         310.1

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0915(3)
_cell_length_b                   10.1014(5)
_cell_length_c                   10.3857(5)
_cell_angle_alpha                86.948(2)
_cell_angle_beta                 70.9880(10)
_cell_angle_gamma                86.6970(10)
_cell_volume                     701.75(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    5101
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      29.66

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9674
_exptl_absorpt_correction_T_max  0.989

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_number            10745
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2862
_reflns_number_gt                2204
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0465P)²+0.1398P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.007(2)
_refine_ls_number_reflns         2862
_refine_ls_number_parameters     210
_refine_ls_number_restraints     65
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.63148(11) 0.27800(7) 0.86942(8) 0.0218(2) Uani 1 1 d U . .
F2 F 0.96415(11) 0.26969(8) 0.83669(8) 0.0241(2) Uani 1 1 d U . .
O2 O 0.81497(14) 0.07853(9) 0.81803(9) 0.0217(2) Uani 1 1 d U . .
N7 N 0.64851(15) 0.12369(11) 1.32923(11) 0.0177(3) Uani 1 1 d U . .
N14 N 0.74366(15) 0.17384(11) 1.04786(11) 0.0153(3) Uani 1 1 d U . .
B B 0.7895(2) 0.20223(15) 0.88865(15) 0.0174(3) Uani 1 1 d U . .
C3 C 0.78296(18) -0.04145(13) 0.87737(13) 0.0156(3) Uani 1 1 d U . .
C4 C 0.73312(18) -0.05895(13) 1.01486(13) 0.0167(3) Uani 1 1 d U . .
H4 H 0.7111 -0.146 1.0544 0.02 Uiso 1 1 calc R . .
C5 C 0.71301(18) 0.04906(13) 1.10132(13) 0.0149(3) Uani 1 1 d U . .
C6 C 0.65830(18) 0.02717(13) 1.24837(13) 0.0161(3) Uani 1 1 d U . .
C8 C 0.68338(19) 0.24991(13) 1.27393(13) 0.0174(3) Uani 1 1 d U . .
C9 C 0.6681(2) 0.35397(14) 1.36252(14) 0.0213(3) Uani 1 1 d U . .
H9 H 0.6412 0.3349 1.4572 0.026 Uiso 1 1 calc R . .
C10 C 0.6919(2) 0.48205(14) 1.31302(15) 0.0242(3) Uani 1 1 d U . .
H10 H 0.6805 0.5519 1.3732 0.029 Uiso 1 1 calc R . .
C11 C 0.7331(2) 0.51036(14) 1.17297(15) 0.0234(3) Uani 1 1 d U . .
H11 H 0.7487 0.5998 1.1394 0.028 Uiso 1 1 calc R . .
C12 C 0.7515(2) 0.41120(13) 1.08349(14) 0.0209(3) Uani 1 1 d U . .
H12 H 0.7803 0.4319 0.9889 0.025 Uiso 1 1 calc R . .
C13 C 0.72731(18) 0.27896(13) 1.13305(13) 0.0168(3) Uani 1 1 d U . .
C15 C 0.6069(2) -0.10847(13) 1.31135(13) 0.0209(3) Uani 1 1 d U . .
H15A H 0.4989 -0.141 1.2836 0.031 Uiso 1 1 calc R . .
H15B H 0.5635 -0.1041 1.4108 0.031 Uiso 1 1 calc R . .
H15C H 0.7246 -0.169 1.2808 0.031 Uiso 1 1 calc R . .
C16 C 0.80677(18) -0.14896(13) 0.78121(13) 0.0162(3) Uani 1 1 d U . .
C17 C 0.8702(2) -0.11854(14) 0.64113(14) 0.0212(3) Uani 1 1 d U . .
H17 H 0.8972 -0.0296 0.609 0.025 Uiso 1 1 calc R . .
C18 C 0.8939(2) -0.21761(15) 0.54872(14) 0.0242(3) Uani 1 1 d U . .
H18 H 0.9383 -0.1964 0.4537 0.029 Uiso 1 1 calc R . .
C19 C 0.8530(2) -0.34687(14) 0.59483(15) 0.0229(3) Uani 1 1 d U . .
H19 H 0.869 -0.4143 0.5313 0.027 Uiso 1 1 calc R . .
C20 C 0.7886(2) -0.37881(14) 0.73341(15) 0.0238(3) Uani 1 1 d U . .
H20 H 0.7603 -0.4679 0.7648 0.029 Uiso 1 1 calc R . .
C21 C 0.7657(2) -0.28022(14) 0.82625(14) 0.0204(3) Uani 1 1 d U . .
H21 H 0.7219 -0.3022 0.9211 0.024 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
F1 B 1.3829(17) . ?
F2 B 1.3827(17) . ?
O2 C3 1.3271(15) . ?
O2 B 1.4551(17) . ?
N7 C6 1.3046(16) . ?
N7 C8 1.3720(17) . ?
N14 C5 1.3501(17) . ?
N14 C13 1.3939(16) . ?
N14 B 1.5912(18) . ?
C3 C4 1.3589(18) . ?
C3 C16 1.4799(18) . ?
C4 C5 1.4212(18) . ?
C4 H4 0.95 . ?
C5 C6 1.4559(18) . ?
C6 C15 1.4983(18) . ?
C8 C9 1.4101(18) . ?
C8 C13 1.4113(18) . ?
C9 C10 1.365(2) . ?
C9 H9 0.95 . ?
C10 C11 1.404(2) . ?
C10 H10 0.95 . ?
C11 C12 1.3745(19) . ?
C11 H11 0.95 . ?
C12 C13 1.4052(19) . ?
C12 H12 0.95 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 C21 1.3968(19) . ?
C16 C17 1.3983(18) . ?
C17 C18 1.3887(19) . ?
C17 H17 0.95 . ?
C18 C19 1.380(2) . ?
C18 H18 0.95 . ?
C19 C20 1.387(2) . ?
C19 H19 0.95 . ?
C20 C21 1.3891(19) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?

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 O2 B 125.52(10) . . ?
C6 N7 C8 118.73(11) . . ?
C5 N14 C13 119.91(11) . . ?
C5 N14 B 120.24(11) . . ?
C13 N14 B 119.79(11) . . ?
F2 B F1 110.21(11) . . ?
F2 B O2 108.32(11) . . ?
F1 B O2 109.87(11) . . ?
F2 B N14 109.41(11) . . ?
F1 B N14 108.36(11) . . ?
O2 B N14 110.65(11) . . ?
O2 C3 C4 120.93(12) . . ?
O2 C3 C16 114.08(11) . . ?
C4 C3 C16 124.98(12) . . ?
C3 C4 C5 122.01(12) . . ?
C3 C4 H4 119 . . ?
C5 C4 H4 119 . . ?
N14 C5 C4 120.24(12) . . ?
N14 C5 C6 119.05(11) . . ?
C4 C5 C6 120.71(12) . . ?
N7 C6 C5 121.83(12) . . ?
N7 C6 C15 118.01(12) . . ?
C5 C6 C15 120.15(11) . . ?
N7 C8 C9 118.29(12) . . ?
N7 C8 C13 122.28(12) . . ?
C9 C8 C13 119.40(13) . . ?
C10 C9 C8 120.39(13) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.88(13) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 121.27(13) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.45(13) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
N14 C13 C12 122.33(12) . . ?
N14 C13 C8 118.08(12) . . ?
C12 C13 C8 119.60(12) . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 118.82(12) . . ?
C21 C16 C3 121.92(12) . . ?
C17 C16 C3 119.26(12) . . ?
C18 C17 C16 120.41(13) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.08(13) . . ?
C19 C18 H18 120 . . ?
C17 C18 H18 120 . . ?
C18 C19 C20 120.34(13) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C21 119.81(13) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 120.54(13) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O2 B F2 127.04(12) . . . . ?
C3 O2 B F1 -112.51(13) . . . . ?
C3 O2 B N14 7.11(17) . . . . ?
C5 N14 B F2 -126.05(12) . . . . ?
C13 N14 B F2 56.49(15) . . . . ?
C5 N14 B F1 113.75(13) . . . . ?
C13 N14 B F1 -63.70(14) . . . . ?
C5 N14 B O2 -6.78(16) . . . . ?
C13 N14 B O2 175.77(10) . . . . ?
B O2 C3 C4 -4.16(19) . . . . ?
B O2 C3 C16 175.88(11) . . . . ?
O2 C3 C4 C5 0.0(2) . . . . ?
C16 C3 C4 C5 179.92(11) . . . . ?
C13 N14 C5 C4 -178.81(11) . . . . ?
B N14 C5 C4 3.74(17) . . . . ?
C13 N14 C5 C6 1.49(17) . . . . ?
B N14 C5 C6 -175.96(10) . . . . ?
C3 C4 C5 N14 -0.05(19) . . . . ?
C3 C4 C5 C6 179.64(11) . . . . ?
C8 N7 C6 C5 2.57(18) . . . . ?
C8 N7 C6 C15 -176.12(11) . . . . ?
N14 C5 C6 N7 -3.74(18) . . . . ?
C4 C5 C6 N7 176.56(11) . . . . ?
N14 C5 C6 C15 174.92(11) . . . . ?
C4 C5 C6 C15 -4.78(18) . . . . ?
C6 N7 C8 C9 178.63(11) . . . . ?
C6 N7 C8 C13 0.68(18) . . . . ?
N7 C8 C9 C10 -176.77(12) . . . . ?
C13 C8 C9 C10 1.24(19) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C5 N14 C13 C12 -177.97(12) . . . . ?
B N14 C13 C12 -0.51(18) . . . . ?
C5 N14 C13 C8 1.55(17) . . . . ?
B N14 C13 C8 179.01(11) . . . . ?
C11 C12 C13 N14 179.89(12) . . . . ?
C11 C12 C13 C8 0.38(19) . . . . ?
N7 C8 C13 N14 -2.79(18) . . . . ?
C9 C8 C13 N14 179.28(11) . . . . ?
N7 C8 C13 C12 176.74(12) . . . . ?
C9 C8 C13 C12 -1.19(19) . . . . ?
O2 C3 C16 C21 -175.60(11) . . . . ?
C4 C3 C16 C21 4.4(2) . . . . ?
O2 C3 C16 C17 3.74(17) . . . . ?
C4 C3 C16 C17 -176.21(12) . . . . ?
C21 C16 C17 C18 -0.7(2) . . . . ?
C3 C16 C17 C18 179.95(11) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C17 C18 C19 C20 -0.2(2) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
C19 C20 C21 C16 0.1(2) . . . . ?
C17 C16 C21 C20 0.34(19) . . . . ?
C3 C16 C21 C20 179.68(12) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_i14597
_database_code_depnum_ccdc_archive 'CCDC 953118'
_audit_update_record             
;
2013-07-30 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H22 B F2 N3 O'
_chemical_formula_sum            'C29 H22 B F2 N3 O'
_chemical_formula_weight         477.31

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.0013(6)
_cell_length_b                   6.9212(2)
_cell_length_c                   20.2630(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.034(2)
_cell_angle_gamma                90
_cell_volume                     2268.42(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    9143
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      31.11

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       niddle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_T_max  0.9885

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_number            35985
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             4648
_reflns_number_gt                3197
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0425P)²+0.6796P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_number_reflns         4648
_refine_ls_number_parameters     327
_refine_ls_number_restraints     101
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.31879(6) 0.62214(14) 0.38075(5) 0.0237(3) Uani 1 1 d U . .
F2 F 0.32497(6) 0.94947(13) 0.37992(5) 0.0235(3) Uani 1 1 d U . .
O2 O 0.39564(7) 0.78710(17) 0.48866(6) 0.0215(3) Uani 1 1 d U . .
N7 N 0.58095(9) 0.72800(18) 0.35989(8) 0.0181(3) Uani 1 1 d U . .
N14 N 0.44515(9) 0.76742(18) 0.39179(7) 0.0158(3) Uani 1 1 d U . .
N22 N 0.48911(9) 0.73808(19) 0.82571(7) 0.0175(3) Uani 1 1 d U . .
B1 B 0.36832(12) 0.7829(3) 0.40970(10) 0.0175(4) Uani 1 1 d U . .
C3 C 0.47242(10) 0.7612(2) 0.53938(9) 0.0154(4) Uani 1 1 d U . .
C4 C 0.53544(11) 0.7401(2) 0.52008(9) 0.0164(4) Uani 1 1 d U . .
H4 H 0.59 0.7217 0.5575 0.02 Uiso 1 1 calc R . .
C5 C 0.52184(10) 0.7448(2) 0.44619(9) 0.0151(4) Uani 1 1 d U . .
C6 C 0.59055(11) 0.7245(2) 0.42747(9) 0.0174(4) Uani 1 1 d U . .
C8 C 0.50238(11) 0.7519(2) 0.30481(9) 0.0180(4) Uani 1 1 d U . .
C9 C 0.49150(12) 0.7546(2) 0.23188(9) 0.0220(4) Uani 1 1 d U . .
H9 H 0.5381 0.7441 0.2217 0.026 Uiso 1 1 calc R . .
C10 C 0.41419(12) 0.7720(2) 0.17546(10) 0.0241(4) Uani 1 1 d U . .
H10 H 0.4071 0.7734 0.1261 0.029 Uiso 1 1 calc R . .
C11 C 0.34560(12) 0.7879(2) 0.19010(10) 0.0239(4) Uani 1 1 d U . .
H11 H 0.292 0.799 0.1504 0.029 Uiso 1 1 calc R . .
C12 C 0.35420(12) 0.7877(2) 0.26055(9) 0.0218(4) Uani 1 1 d U . .
H12 H 0.307 0.7992 0.2698 0.026 Uiso 1 1 calc R . .
C13 C 0.43326(11) 0.7704(2) 0.31907(9) 0.0171(4) Uani 1 1 d U . .
C15 C 0.67594(11) 0.7014(2) 0.48755(9) 0.0203(4) Uani 1 1 d U . .
H15A H 0.715 0.6865 0.4662 0.03 Uiso 1 1 calc R . .
H15B H 0.6782 0.5867 0.5167 0.03 Uiso 1 1 calc R . .
H15C H 0.6907 0.8159 0.5192 0.03 Uiso 1 1 calc R . .
C16 C 0.48095(10) 0.7595(2) 0.61445(9) 0.0154(4) Uani 1 1 d U . .
C17 C 0.41369(11) 0.8126(2) 0.62725(9) 0.0171(4) Uani 1 1 d U . .
H17 H 0.3639 0.8518 0.5869 0.021 Uiso 1 1 calc R . .
C18 C 0.41718(11) 0.8099(2) 0.69614(9) 0.0178(4) Uani 1 1 d U . .
H18 H 0.3705 0.8506 0.7028 0.021 Uiso 1 1 calc R . .
C19 C 0.48840(11) 0.7482(2) 0.75671(9) 0.0153(4) Uani 1 1 d U . .
C20 C 0.55679(11) 0.6964(2) 0.74466(9) 0.0162(4) Uani 1 1 d U . .
H20 H 0.6064 0.6556 0.7849 0.019 Uiso 1 1 calc R . .
C21 C 0.55311(11) 0.7039(2) 0.67532(9) 0.0163(4) Uani 1 1 d U . .
H21 H 0.6006 0.6705 0.6688 0.02 Uiso 1 1 calc R . .
C23 C 0.55912(10) 0.6832(2) 0.89137(9) 0.0160(4) Uani 1 1 d U . .
C24 C 0.54814(11) 0.5462(2) 0.93662(9) 0.0192(4) Uani 1 1 d U . .
H24 H 0.4953 0.4893 0.9225 0.023 Uiso 1 1 calc R . .
C25 C 0.61353(11) 0.4924(2) 1.00179(10) 0.0211(4) Uani 1 1 d U . .
H25 H 0.6055 0.3995 1.0326 0.025 Uiso 1 1 calc R . .
C26 C 0.69058(11) 0.5733(2) 1.02234(10) 0.0213(4) Uani 1 1 d U . .
H26 H 0.7357 0.5361 1.0671 0.026 Uiso 1 1 calc R . .
C27 C 0.70183(11) 0.7089(2) 0.97735(9) 0.0201(4) Uani 1 1 d U . .
H27 H 0.7549 0.7639 0.9912 0.024 Uiso 1 1 calc R . .
C28 C 0.63641(11) 0.7648(2) 0.91249(9) 0.0182(4) Uani 1 1 d U . .
H28 H 0.6445 0.8594 0.8823 0.022 Uiso 1 1 calc R . .
C29 C 0.41596(11) 0.7831(2) 0.83430(9) 0.0192(4) Uani 1 1 d U . .
C30 C 0.34587(12) 0.6696(3) 0.80182(10) 0.0295(5) Uani 1 1 d U . .
H30 H 0.3457 0.5597 0.7736 0.035 Uiso 1 1 calc R . .
C31 C 0.27633(13) 0.7164(4) 0.81049(12) 0.0445(6) Uani 1 1 d U . .
H31 H 0.2278 0.64 0.7873 0.053 Uiso 1 1 calc R . .
C32 C 0.27652(15) 0.8719(4) 0.85223(13) 0.0518(7) Uani 1 1 d U . .
H32 H 0.2283 0.9036 0.8578 0.062 Uiso 1 1 calc R . .
C33 C 0.34690(16) 0.9826(3) 0.88613(13) 0.0459(6) Uani 1 1 d U . .
H33 H 0.3473 1.0891 0.9159 0.055 Uiso 1 1 calc R . .
C34 C 0.41740(13) 0.9394(3) 0.87713(10) 0.0292(5) Uani 1 1 d U . .
H34 H 0.4658 1.0164 0.9001 0.035 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
F1 B1 1.385(2) . ?
F2 B1 1.374(2) . ?
O2 C3 1.324(2) . ?
O2 B1 1.453(2) . ?
N7 C6 1.303(2) . ?
N7 C8 1.374(2) . ?
N14 C5 1.345(2) . ?
N14 C13 1.393(2) . ?
N14 B1 1.580(2) . ?
N22 C19 1.394(2) . ?
N22 C23 1.425(2) . ?
N22 C29 1.436(2) . ?
C3 C4 1.360(2) . ?
C3 C16 1.460(2) . ?
C4 C5 1.408(2) . ?
C4 H4 0.95 . ?
C5 C6 1.451(2) . ?
C6 C15 1.493(2) . ?
C8 C13 1.401(2) . ?
C8 C9 1.403(2) . ?
C9 C10 1.364(3) . ?
C9 H9 0.95 . ?
C10 C11 1.395(3) . ?
C10 H10 0.95 . ?
C11 C12 1.367(2) . ?
C11 H11 0.95 . ?
C12 C13 1.402(2) . ?
C12 H12 0.95 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 C17 1.394(2) . ?
C16 C21 1.397(2) . ?
C17 C18 1.370(2) . ?
C17 H17 0.95 . ?
C18 C19 1.397(2) . ?
C18 H18 0.95 . ?
C19 C20 1.403(2) . ?
C20 C21 1.378(2) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
C23 C28 1.384(2) . ?
C23 C24 1.392(2) . ?
C24 C25 1.380(2) . ?
C24 H24 0.95 . ?
C25 C26 1.380(2) . ?
C25 H25 0.95 . ?
C26 C27 1.384(2) . ?
C26 H26 0.95 . ?
C27 C28 1.380(2) . ?
C27 H27 0.95 . ?
C28 H28 0.95 . ?
C29 C34 1.380(2) . ?
C29 C30 1.383(3) . ?
C30 C31 1.377(3) . ?
C30 H30 0.95 . ?
C31 C32 1.368(4) . ?
C31 H31 0.95 . ?
C32 C33 1.378(4) . ?
C32 H32 0.95 . ?
C33 C34 1.391(3) . ?
C33 H33 0.95 . ?
C34 H34 0.95 . ?

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 O2 B1 125.86(13) . . ?
C6 N7 C8 118.06(15) . . ?
C5 N14 C13 119.64(15) . . ?
C5 N14 B1 120.43(13) . . ?
C13 N14 B1 119.89(14) . . ?
C19 N22 C23 124.38(14) . . ?
C19 N22 C29 120.36(14) . . ?
C23 N22 C29 115.26(13) . . ?
F2 B1 F1 110.62(15) . . ?
F2 B1 O2 108.62(14) . . ?
F1 B1 O2 109.04(14) . . ?
F2 B1 N14 109.98(14) . . ?
F1 B1 N14 108.28(13) . . ?
O2 B1 N14 110.29(14) . . ?
O2 C3 C4 120.64(15) . . ?
O2 C3 C16 113.98(14) . . ?
C4 C3 C16 125.38(16) . . ?
C3 C4 C5 121.72(16) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
N14 C5 C4 120.74(15) . . ?
N14 C5 C6 118.88(14) . . ?
C4 C5 C6 120.38(15) . . ?
N7 C6 C5 122.53(16) . . ?
N7 C6 C15 118.25(15) . . ?
C5 C6 C15 119.21(14) . . ?
N7 C8 C13 122.29(15) . . ?
N7 C8 C9 118.37(16) . . ?
C13 C8 C9 119.33(16) . . ?
C10 C9 C8 120.22(17) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.08(16) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C12 C11 C10 121.13(18) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.42(17) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
N14 C13 C8 118.59(16) . . ?
N14 C13 C12 121.59(16) . . ?
C8 C13 C12 119.81(15) . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.10(15) . . ?
C17 C16 C3 119.26(15) . . ?
C21 C16 C3 123.63(15) . . ?
C18 C17 C16 122.07(16) . . ?
C18 C17 H17 119 . . ?
C16 C17 H17 119 . . ?
C17 C18 C19 120.88(16) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
N22 C19 C18 119.81(15) . . ?
N22 C19 C20 122.64(15) . . ?
C18 C19 C20 117.55(15) . . ?
C21 C20 C19 120.98(16) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 121.37(16) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
C28 C23 C24 119.24(16) . . ?
C28 C23 N22 122.48(15) . . ?
C24 C23 N22 118.26(15) . . ?
C25 C24 C23 120.39(16) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.13(16) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C27 119.65(17) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C28 C27 C26 120.47(17) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C23 120.12(16) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?
C34 C29 C30 120.39(18) . . ?
C34 C29 N22 118.75(17) . . ?
C30 C29 N22 120.84(16) . . ?
C31 C30 C29 119.7(2) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C32 C31 C30 120.5(2) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C33 119.9(2) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C32 C33 C34 120.5(2) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C29 C34 C33 119.0(2) . . ?
C29 C34 H34 120.5 . . ?
C33 C34 H34 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O2 B1 F2 -127.32(16) . . . . ?
C3 O2 B1 F1 112.05(17) . . . . ?
C3 O2 B1 N14 -6.7(2) . . . . ?
C5 N14 B1 F2 125.04(15) . . . . ?
C13 N14 B1 F2 -57.22(19) . . . . ?
C5 N14 B1 F1 -113.98(15) . . . . ?
C13 N14 B1 F1 63.76(18) . . . . ?
C5 N14 B1 O2 5.3(2) . . . . ?
C13 N14 B1 O2 -177.00(13) . . . . ?
B1 O2 C3 C4 4.5(2) . . . . ?
B1 O2 C3 C16 -175.87(14) . . . . ?
O2 C3 C4 C5 0.0(2) . . . . ?
C16 C3 C4 C5 -179.58(14) . . . . ?
C13 N14 C5 C4 -179.61(14) . . . . ?
B1 N14 C5 C4 -1.9(2) . . . . ?
C13 N14 C5 C6 0.2(2) . . . . ?
B1 N14 C5 C6 177.94(14) . . . . ?
C3 C4 C5 N14 -1.1(2) . . . . ?
C3 C4 C5 C6 179.12(14) . . . . ?
C8 N7 C6 C5 0.0(2) . . . . ?
C8 N7 C6 C15 -179.13(13) . . . . ?
N14 C5 C6 N7 0.2(2) . . . . ?
C4 C5 C6 N7 -179.98(15) . . . . ?
N14 C5 C6 C15 179.35(14) . . . . ?
C4 C5 C6 C15 -0.8(2) . . . . ?
C6 N7 C8 C13 -0.7(2) . . . . ?
C6 N7 C8 C9 -179.59(14) . . . . ?
N7 C8 C9 C10 177.99(15) . . . . ?
C13 C8 C9 C10 -1.0(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C5 N14 C13 C8 -0.8(2) . . . . ?
B1 N14 C13 C8 -178.55(14) . . . . ?
C5 N14 C13 C12 178.01(14) . . . . ?
B1 N14 C13 C12 0.3(2) . . . . ?
N7 C8 C13 N14 1.1(2) . . . . ?
C9 C8 C13 N14 179.97(14) . . . . ?
N7 C8 C13 C12 -177.77(14) . . . . ?
C9 C8 C13 C12 1.1(2) . . . . ?
C11 C12 C13 N14 -179.30(15) . . . . ?
C11 C12 C13 C8 -0.5(2) . . . . ?
O2 C3 C16 C17 -9.5(2) . . . . ?
C4 C3 C16 C17 170.06(15) . . . . ?
O2 C3 C16 C21 169.30(14) . . . . ?
C4 C3 C16 C21 -11.1(2) . . . . ?
C21 C16 C17 C18 -0.4(2) . . . . ?
C3 C16 C17 C18 178.55(15) . . . . ?
C16 C17 C18 C19 -1.8(2) . . . . ?
C23 N22 C19 C18 -177.88(15) . . . . ?
C29 N22 C19 C18 2.6(2) . . . . ?
C23 N22 C19 C20 2.8(2) . . . . ?
C29 N22 C19 C20 -176.69(15) . . . . ?
C17 C18 C19 N22 -176.98(15) . . . . ?
C17 C18 C19 C20 2.4(2) . . . . ?
N22 C19 C20 C21 178.43(15) . . . . ?
C18 C19 C20 C21 -0.9(2) . . . . ?
C19 C20 C21 C16 -1.2(2) . . . . ?
C17 C16 C21 C20 1.9(2) . . . . ?
C3 C16 C21 C20 -177.01(15) . . . . ?
C19 N22 C23 C28 49.9(2) . . . . ?
C29 N22 C23 C28 -130.53(17) . . . . ?
C19 N22 C23 C24 -131.91(16) . . . . ?
C29 N22 C23 C24 47.6(2) . . . . ?
C28 C23 C24 C25 0.1(2) . . . . ?
N22 C23 C24 C25 -178.16(15) . . . . ?
C23 C24 C25 C26 -0.5(2) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
C25 C26 C27 C28 0.6(3) . . . . ?
C26 C27 C28 C23 -1.0(3) . . . . ?
C24 C23 C28 C27 0.7(2) . . . . ?
N22 C23 C28 C27 178.81(15) . . . . ?
C19 N22 C29 C34 -116.49(18) . . . . ?
C23 N22 C29 C34 64.0(2) . . . . ?
C19 N22 C29 C30 65.0(2) . . . . ?
C23 N22 C29 C30 -114.52(18) . . . . ?
C34 C29 C30 C31 2.0(3) . . . . ?
N22 C29 C30 C31 -179.60(16) . . . . ?
C29 C30 C31 C32 -1.4(3) . . . . ?
C30 C31 C32 C33 -0.2(3) . . . . ?
C31 C32 C33 C34 1.2(3) . . . . ?
C30 C29 C34 C33 -1.0(3) . . . . ?
N22 C29 C34 C33 -179.45(16) . . . . ?
C32 C33 C34 C29 -0.6(3) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_i14633
_database_code_depnum_ccdc_archive 'CCDC 966717'
_audit_update_record             
;
2013-10-16 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H15 B F2 N2 O'
_chemical_formula_sum            'C22 H15 B F2 N2 O'
_chemical_formula_weight         372.17

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1054(7)
_cell_length_b                   11.1114(10)
_cell_length_c                   11.9627(12)
_cell_angle_alpha                96.493(3)
_cell_angle_beta                 106.301(3)
_cell_angle_gamma                105.521(2)
_cell_volume                     855.17(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    7848
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      29.96

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_T_max  0.9877

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_number            13395
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3761
_reflns_number_gt                3050
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1103P)²+0.0979P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3761
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1463
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.085

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.42408(13) 0.21801(9) 0.93191(8) 0.0191(2) Uani 1 1 d . . .
F2 F 0.74964(14) 0.21363(8) 0.95141(8) 0.0185(2) Uani 1 1 d . . .
O1 O 0.70023(17) 0.38093(10) 1.06340(9) 0.0169(3) Uani 1 1 d . . .
N1 N 0.63085(19) 0.36341(12) 0.84230(11) 0.0124(3) Uani 1 1 d . . .
N2 N 0.66583(19) 0.49060(12) 0.65534(11) 0.0142(3) Uani 1 1 d . . .
B1 B 0.6250(3) 0.28975(17) 0.94999(15) 0.0148(4) Uani 1 1 d . . .
C1 C 0.7785(2) 0.50630(14) 1.07700(13) 0.0132(3) Uani 1 1 d . . .
C2 C 0.7878(2) 0.56285(15) 0.98253(13) 0.0142(3) Uani 1 1 d . . .
H2 H 0.8474 0.6528 0.9964 0.017 Uiso 1 1 calc R . .
C3 C 0.7113(2) 0.49146(14) 0.86398(13) 0.0128(3) Uani 1 1 d . . .
C4 C 0.7239(2) 0.55424(14) 0.76462(13) 0.0130(3) Uani 1 1 d . . .
C5 C 0.5796(2) 0.36035(15) 0.63405(13) 0.0136(3) Uani 1 1 d . . .
C6 C 0.5055(2) 0.29273(15) 0.51484(14) 0.0168(3) Uani 1 1 d . . .
H6 H 0.5193 0.3372 0.4528 0.02 Uiso 1 1 calc R . .
C7 C 0.4139(2) 0.16319(16) 0.48862(14) 0.0190(4) Uani 1 1 d . . .
H7 H 0.3621 0.1179 0.4084 0.023 Uiso 1 1 calc R . .
C8 C 0.3967(2) 0.09746(15) 0.58108(14) 0.0189(4) Uani 1 1 d . . .
H8 H 0.3349 0.0074 0.5623 0.023 Uiso 1 1 calc R . .
C9 C 0.4674(2) 0.16045(15) 0.69801(14) 0.0166(3) Uani 1 1 d . . .
H9 H 0.4548 0.1143 0.7591 0.02 Uiso 1 1 calc R . .
C10 C 0.5587(2) 0.29402(15) 0.72612(13) 0.0136(3) Uani 1 1 d . . .
C11 C 0.8498(2) 0.57857(15) 1.20073(13) 0.0137(3) Uani 1 1 d . . .
C12 C 0.7991(2) 0.51898(15) 1.29026(13) 0.0154(3) Uani 1 1 d . . .
H12 H 0.7225 0.4308 1.2718 0.019 Uiso 1 1 calc R . .
C13 C 0.8599(2) 0.58770(16) 1.40584(13) 0.0181(3) Uani 1 1 d . . .
H13 H 0.8249 0.5467 1.466 0.022 Uiso 1 1 calc R . .
C14 C 0.9722(2) 0.71691(16) 1.43316(14) 0.0186(4) Uani 1 1 d . . .
H14 H 1.0134 0.7642 1.512 0.022 Uiso 1 1 calc R . .
C15 C 1.0242(2) 0.77668(16) 1.34530(14) 0.0177(3) Uani 1 1 d . . .
H15 H 1.101 0.8648 1.3643 0.021 Uiso 1 1 calc R . .
C16 C 0.9644(2) 0.70837(15) 1.23002(13) 0.0153(3) Uani 1 1 d . . .
H16 H 1.0013 0.7498 1.1705 0.018 Uiso 1 1 calc R . .
C17 C 0.8139(2) 0.69566(14) 0.78490(12) 0.0144(3) Uani 1 1 d . . .
C18 C 0.7333(2) 0.77880(15) 0.83846(13) 0.0182(3) Uani 1 1 d . . .
H18 H 0.6157 0.7457 0.862 0.022 Uiso 1 1 calc R . .
C19 C 0.8246(3) 0.90998(16) 0.85745(14) 0.0230(4) Uani 1 1 d . . .
H19 H 0.7687 0.9664 0.8933 0.028 Uiso 1 1 calc R . .
C20 C 0.9975(3) 0.95866(16) 0.82410(14) 0.0248(4) Uani 1 1 d . . .
H20 H 1.0622 1.0482 0.8391 0.03 Uiso 1 1 calc R . .
C21 C 1.0754(3) 0.87623(17) 0.76887(15) 0.0239(4) Uani 1 1 d . . .
H21 H 1.1926 0.9095 0.7451 0.029 Uiso 1 1 calc R . .
C22 C 0.9829(2) 0.74534(16) 0.74809(13) 0.0188(3) Uani 1 1 d . . .
H22 H 1.0352 0.6894 0.7086 0.023 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
F1 B1 1.378(2) . ?
F2 B1 1.3768(19) . ?
O1 C1 1.3265(18) . ?
O1 B1 1.4646(19) . ?
N1 C3 1.3478(19) . ?
N1 C10 1.3911(19) . ?
N1 B1 1.607(2) . ?
N2 C4 1.3082(19) . ?
N2 C5 1.375(2) . ?
C1 C2 1.363(2) . ?
C1 C11 1.478(2) . ?
C2 C3 1.421(2) . ?
C2 H2 0.95 . ?
C3 C4 1.457(2) . ?
C4 C17 1.492(2) . ?
C5 C10 1.412(2) . ?
C5 C6 1.414(2) . ?
C6 C7 1.370(2) . ?
C6 H6 0.95 . ?
C7 C8 1.408(2) . ?
C7 H7 0.95 . ?
C8 C9 1.377(2) . ?
C8 H8 0.95 . ?
C9 C10 1.409(2) . ?
C9 H9 0.95 . ?
C11 C16 1.401(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.95 . ?
C13 C14 1.393(2) . ?
C13 H13 0.95 . ?
C14 C15 1.388(2) . ?
C14 H14 0.95 . ?
C15 C16 1.386(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 C22 1.392(2) . ?
C17 C18 1.396(2) . ?
C18 C19 1.390(2) . ?
C18 H18 0.95 . ?
C19 C20 1.389(3) . ?
C19 H19 0.95 . ?
C20 C21 1.386(3) . ?
C20 H20 0.95 . ?
C21 C22 1.387(2) . ?
C21 H21 0.95 . ?
C22 H22 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 B1 124.87(12) . . ?
C3 N1 C10 119.77(13) . . ?
C3 N1 B1 120.53(12) . . ?
C10 N1 B1 119.66(12) . . ?
C4 N2 C5 118.02(13) . . ?
F2 B1 F1 111.22(13) . . ?
F2 B1 O1 110.06(13) . . ?
F1 B1 O1 108.48(12) . . ?
F2 B1 N1 107.54(12) . . ?
F1 B1 N1 109.02(12) . . ?
O1 B1 N1 110.53(13) . . ?
O1 C1 C2 121.70(14) . . ?
O1 C1 C11 115.07(13) . . ?
C2 C1 C11 123.22(14) . . ?
C1 C2 C3 122.04(15) . . ?
C1 C2 H2 119 . . ?
C3 C2 H2 119 . . ?
N1 C3 C2 120.11(14) . . ?
N1 C3 C4 118.93(13) . . ?
C2 C3 C4 120.93(14) . . ?
N2 C4 C3 122.40(14) . . ?
N2 C4 C17 116.91(13) . . ?
C3 C4 C17 120.64(13) . . ?
N2 C5 C10 122.27(13) . . ?
N2 C5 C6 117.85(14) . . ?
C10 C5 C6 119.86(14) . . ?
C7 C6 C5 120.12(15) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.69(14) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 121.60(15) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 119.34(15) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N1 C10 C9 122.14(14) . . ?
N1 C10 C5 118.49(14) . . ?
C9 C10 C5 119.37(13) . . ?
C16 C11 C12 118.85(14) . . ?
C16 C11 C1 120.71(14) . . ?
C12 C11 C1 120.42(14) . . ?
C13 C12 C11 120.58(15) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.80(15) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.08(14) . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C16 C15 C14 120.28(15) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 120.41(14) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C22 C17 C18 119.39(14) . . ?
C22 C17 C4 118.44(13) . . ?
C18 C17 C4 122.17(13) . . ?
C19 C18 C17 120.12(15) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.09(15) . . ?
C20 C19 H19 120 . . ?
C18 C19 H19 120 . . ?
C21 C20 C19 119.83(15) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.29(15) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.22(15) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 B1 F2 113.43(15) . . . . ?
C1 O1 B1 F1 -124.68(15) . . . . ?
C1 O1 B1 N1 -5.2(2) . . . . ?
C3 N1 B1 F2 -115.74(14) . . . . ?
C10 N1 B1 F2 62.07(17) . . . . ?
C3 N1 B1 F1 123.57(14) . . . . ?
C10 N1 B1 F1 -58.61(17) . . . . ?
C3 N1 B1 O1 4.42(19) . . . . ?
C10 N1 B1 O1 -177.77(12) . . . . ?
B1 O1 C1 C2 2.8(2) . . . . ?
B1 O1 C1 C11 -178.29(13) . . . . ?
O1 C1 C2 C3 1.2(2) . . . . ?
C11 C1 C2 C3 -177.67(13) . . . . ?
C10 N1 C3 C2 -179.15(12) . . . . ?
B1 N1 C3 C2 -1.3(2) . . . . ?
C10 N1 C3 C4 -1.1(2) . . . . ?
B1 N1 C3 C4 176.75(12) . . . . ?
C1 C2 C3 N1 -1.7(2) . . . . ?
C1 C2 C3 C4 -179.76(13) . . . . ?
C5 N2 C4 C3 3.6(2) . . . . ?
C5 N2 C4 C17 -179.03(11) . . . . ?
N1 C3 C4 N2 -2.1(2) . . . . ?
C2 C3 C4 N2 175.95(13) . . . . ?
N1 C3 C4 C17 -179.36(12) . . . . ?
C2 C3 C4 C17 -1.3(2) . . . . ?
C4 N2 C5 C10 -2.1(2) . . . . ?
C4 N2 C5 C6 176.24(13) . . . . ?
N2 C5 C6 C7 -178.48(13) . . . . ?
C10 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C3 N1 C10 C9 -178.01(13) . . . . ?
B1 N1 C10 C9 4.2(2) . . . . ?
C3 N1 C10 C5 2.4(2) . . . . ?
B1 N1 C10 C5 -175.40(12) . . . . ?
C8 C9 C10 N1 179.21(13) . . . . ?
C8 C9 C10 C5 -1.2(2) . . . . ?
N2 C5 C10 N1 -0.9(2) . . . . ?
C6 C5 C10 N1 -179.24(12) . . . . ?
N2 C5 C10 C9 179.54(13) . . . . ?
C6 C5 C10 C9 1.2(2) . . . . ?
O1 C1 C11 C16 169.92(12) . . . . ?
C2 C1 C11 C16 -11.2(2) . . . . ?
O1 C1 C11 C12 -11.8(2) . . . . ?
C2 C1 C11 C12 167.12(14) . . . . ?
C16 C11 C12 C13 0.5(2) . . . . ?
C1 C11 C12 C13 -177.79(13) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C11 0.4(2) . . . . ?
C12 C11 C16 C15 -0.7(2) . . . . ?
C1 C11 C16 C15 177.58(13) . . . . ?
N2 C4 C17 C22 -55.63(19) . . . . ?
C3 C4 C17 C22 121.76(16) . . . . ?
N2 C4 C17 C18 123.92(15) . . . . ?
C3 C4 C17 C18 -58.7(2) . . . . ?
C22 C17 C18 C19 -1.6(2) . . . . ?
C4 C17 C18 C19 178.84(13) . . . . ?
C17 C18 C19 C20 -0.6(2) . . . . ?
C18 C19 C20 C21 1.8(2) . . . . ?
C19 C20 C21 C22 -0.8(2) . . . . ?
C20 C21 C22 C17 -1.4(2) . . . . ?
C18 C17 C22 C21 2.6(2) . . . . ?
C4 C17 C22 C21 -177.85(13) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_i14754
_database_code_depnum_ccdc_archive 'CCDC 966718'
_audit_update_record             
;
2013-10-16 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C34 H24 B F2 N3 O'
_chemical_formula_sum            'C34 H24 B F2 N3 O'
_chemical_formula_weight         539.37

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 2/n'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_Int_Tables_number      13
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   14.9332(5)
_cell_length_b                   11.3243(4)
_cell_length_c                   17.9422(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.526(2)
_cell_angle_gamma                90
_cell_volume                     3024.71(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    7829
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.1

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1120
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_T_max  0.992

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_number            45985
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.709
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             6196
_reflns_number_gt                3590
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+2.2572P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6196
_refine_ls_number_parameters     370
_refine_ls_number_restraints     115
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1745
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.80671(12) 0.23159(16) 0.10250(10) 0.0329(5) Uani 1 d . .
F2 F 0.95896(12) 0.24029(17) 0.12214(9) 0.0331(5) Uani 1 d . .
O1 O 0.89070(14) 0.32144(19) 0.01593(11) 0.0283(5) Uani 1 d . .
N1 N 0.87347(15) 0.4172(2) 0.13924(13) 0.0222(6) Uani 1 d . .
N8 N 0.85848(16) 0.6271(2) 0.21945(14) 0.0254(6) Uani 1 d . .
N19 N 0.89354(17) 0.4270(2) -0.33141(13) 0.0258(6) Uani 1 d . .
B1 B 0.8824(2) 0.2981(3) 0.09450(19) 0.0255(8) Uani 1 d . .
C2 C 0.86984(19) 0.4139(3) 0.21721(16) 0.0249(7) Uani 1 d . .
C3 C 0.8740(2) 0.3078(3) 0.25696(17) 0.0280(8) Uani 1 d . .
H3 H 0.8809 0.235 0.2318 0.034 Uiso 1 calc . .
C4 C 0.8680(2) 0.3100(3) 0.33286(18) 0.0349(8) Uani 1 d . .
H4 H 0.871 0.238 0.3601 0.042 Uiso 1 calc . .
C5 C 0.8577(2) 0.4162(3) 0.37079(17) 0.0339(9) Uani 1 d . .
H5 H 0.8529 0.4157 0.4233 0.041 Uiso 1 calc . .
C6 C 0.8544(2) 0.5203(3) 0.33285(17) 0.0303(8) Uani 1 d . .
H6 H 0.8477 0.5924 0.3589 0.036 Uiso 1 calc . .
C7 C 0.86081(19) 0.5211(3) 0.25531(16) 0.0246(7) Uani 1 d . .
C9 C 0.86228(19) 0.6295(3) 0.14716(16) 0.0240(7) Uani 1 d . .
C10 C 0.86778(18) 0.5223(3) 0.10330(16) 0.0216(7) Uani 1 d . .
C11 C 0.86581(19) 0.5242(3) 0.02422(16) 0.0240(7) Uani 1 d . .
H11 H 0.8541 0.597 -0.0011 0.029 Uiso 1 calc . .
C12 C 0.87987(19) 0.4267(3) -0.01676(16) 0.0222(7) Uani 1 d . .
C13 C 0.88504(19) 0.4262(3) -0.09727(16) 0.0220(7) Uani 1 d . .
C14 C 0.86683(19) 0.3242(3) -0.13936(16) 0.0263(7) Uani 1 d . .
H14 H 0.8528 0.2533 -0.1145 0.032 Uiso 1 calc . .
C15 C 0.8687(2) 0.3237(3) -0.21552(17) 0.0269(7) Uani 1 d . .
H15 H 0.8546 0.2533 -0.2427 0.032 Uiso 1 calc . .
C16 C 0.89127(19) 0.4263(3) -0.25382(16) 0.0229(7) Uani 1 d . .
C17 C 0.91240(19) 0.5273(3) -0.21173(16) 0.0234(7) Uani 1 d . .
H17 H 0.9299 0.597 -0.2362 0.028 Uiso 1 calc . .
C18 C 0.90838(18) 0.5279(3) -0.13567(16) 0.0224(7) Uani 1 d . .
H18 H 0.9217 0.5986 -0.1085 0.027 Uiso 1 calc . .
C20 C 0.9055(2) 0.3197(3) -0.37068(16) 0.0264(7) Uani 1 d . .
C21 C 0.9757(2) 0.2423(3) -0.34799(17) 0.0299(8) Uani 1 d . .
H21 H 1.0164 0.2623 -0.3065 0.036 Uiso 1 calc . .
C22 C 0.9860(2) 0.1376(3) -0.38525(19) 0.0367(9) Uani 1 d . .
H22 H 1.0342 0.0861 -0.3698 0.044 Uiso 1 calc . .
C23 C 0.9263(2) 0.1070(4) -0.4454(2) 0.0427(9) Uani 1 d . .
H23 H 0.9325 0.0338 -0.4703 0.051 Uiso 1 calc . .
C24 C 0.8584(2) 0.1832(3) -0.46853(18) 0.0368(9) Uani 1 d . .
H24 H 0.8183 0.1631 -0.5103 0.044 Uiso 1 calc . .
C25 C 0.8476(2) 0.2890(3) -0.43170(17) 0.0292(8) Uani 1 d . .
H25 H 0.8002 0.3408 -0.4484 0.035 Uiso 1 calc . .
C26 C 0.8745(2) 0.5308(3) -0.37352(16) 0.0248(7) Uani 1 d . .
C27 C 0.8055(2) 0.6060(3) -0.35759(18) 0.0300(8) Uani 1 d . .
H27 H 0.7698 0.5882 -0.3175 0.036 Uiso 1 calc . .
C28 C 0.7885(2) 0.7063(3) -0.39923(19) 0.0362(9) Uani 1 d . .
H28 H 0.7409 0.7573 -0.3877 0.043 Uiso 1 calc . .
C29 C 0.8396(2) 0.7342(3) -0.45791(18) 0.0389(9) Uani 1 d . .
H29 H 0.8274 0.8038 -0.4864 0.047 Uiso 1 calc . .
C30 C 0.9082(2) 0.6600(3) -0.47440(18) 0.0379(9) Uani 1 d . .
H30 H 0.9436 0.678 -0.5146 0.045 Uiso 1 calc . .
C31 C 0.9253(2) 0.5594(3) -0.43245(17) 0.0307(8) Uani 1 d . .
H31 H 0.9729 0.5086 -0.4441 0.037 Uiso 1 calc . .
C32 C 0.8588(2) 0.7480(3) 0.11081(16) 0.0254(7) Uani 1 d . .
C33 C 0.9163(2) 0.7807(3) 0.05733(17) 0.0292(8) Uani 1 d . .
H33 H 0.9601 0.7263 0.0427 0.035 Uiso 1 calc . .
C34 C 0.9105(2) 0.8917(3) 0.02501(19) 0.0368(9) Uani 1 d . .
H34 H 0.9498 0.9129 -0.0119 0.044 Uiso 1 calc . .
C35 C 0.8482(3) 0.9709(3) 0.0461(2) 0.0434(9) Uani 1 d . .
H35 H 0.8432 1.0462 0.0228 0.052 Uiso 1 calc . .
C36 C 0.7921(3) 0.9416(3) 0.1014(2) 0.0429(9) Uani 1 d . .
H36 H 0.7504 0.9978 0.1173 0.051 Uiso 1 calc . .
C37 C 0.7970(2) 0.8296(3) 0.13381(18) 0.0340(8) Uani 1 d . .
H37 H 0.7583 0.8091 0.1714 0.041 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
F1 B1 1.375(4) . ?
F2 B1 1.375(4) . ?
O1 C12 1.332(4) . ?
O1 B1 1.449(4) . ?
N1 C10 1.353(4) . ?
N1 C2 1.405(4) . ?
N1 B1 1.581(4) . ?
N8 C9 1.303(4) . ?
N8 C7 1.361(4) . ?
N19 C16 1.395(4) . ?
N19 C26 1.414(4) . ?
N19 C20 1.423(4) . ?
C2 C3 1.396(4) . ?
C2 C7 1.405(4) . ?
C3 C4 1.372(4) . ?
C3 H3 0.95 . ?
C4 C5 1.396(5) . ?
C4 H4 0.95 . ?
C5 C6 1.361(5) . ?
C5 H5 0.95 . ?
C6 C7 1.402(4) . ?
C6 H6 0.95 . ?
C9 C10 1.452(4) . ?
C9 C32 1.490(4) . ?
C10 C11 1.417(4) . ?
C11 C12 1.353(4) . ?
C11 H11 0.95 . ?
C12 C13 1.453(4) . ?
C13 C14 1.395(4) . ?
C13 C18 1.400(4) . ?
C14 C15 1.369(4) . ?
C14 H14 0.95 . ?
C15 C16 1.404(4) . ?
C15 H15 0.95 . ?
C16 C17 1.393(4) . ?
C17 C18 1.371(4) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
C20 C25 1.385(4) . ?
C20 C21 1.401(4) . ?
C21 C22 1.376(5) . ?
C21 H21 0.95 . ?
C22 C23 1.388(5) . ?
C22 H22 0.95 . ?
C23 C24 1.370(5) . ?
C23 H23 0.95 . ?
C24 C25 1.384(5) . ?
C24 H24 0.95 . ?
C25 H25 0.95 . ?
C26 C27 1.384(4) . ?
C26 C31 1.388(4) . ?
C27 C28 1.372(5) . ?
C27 H27 0.95 . ?
C28 C29 1.385(5) . ?
C28 H28 0.95 . ?
C29 C30 1.375(5) . ?
C29 H29 0.95 . ?
C30 C31 1.378(5) . ?
C30 H30 0.95 . ?
C31 H31 0.95 . ?
C32 C33 1.387(4) . ?
C32 C37 1.392(4) . ?
C33 C34 1.384(5) . ?
C33 H33 0.95 . ?
C34 C35 1.367(5) . ?
C34 H34 0.95 . ?
C35 C36 1.389(5) . ?
C35 H35 0.95 . ?
C36 C37 1.394(5) . ?
C36 H36 0.95 . ?
C37 H37 0.95 . ?

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
C12 O1 B1 125.1(3) . . ?
C10 N1 C2 119.5(3) . . ?
C10 N1 B1 120.9(2) . . ?
C2 N1 B1 119.6(3) . . ?
C9 N8 C7 119.2(3) . . ?
C16 N19 C26 121.2(3) . . ?
C16 N19 C20 120.2(3) . . ?
C26 N19 C20 118.2(2) . . ?
F2 B1 F1 111.6(3) . . ?
F2 B1 O1 107.8(3) . . ?
F1 B1 O1 109.6(3) . . ?
F2 B1 N1 108.9(2) . . ?
F1 B1 N1 108.1(3) . . ?
O1 B1 N1 110.8(3) . . ?
C3 C2 N1 121.9(3) . . ?
C3 C2 C7 119.8(3) . . ?
N1 C2 C7 118.3(3) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120 . . ?
C7 C6 H6 120 . . ?
N8 C7 C6 118.3(3) . . ?
N8 C7 C2 122.1(3) . . ?
C6 C7 C2 119.6(3) . . ?
N8 C9 C10 122.0(3) . . ?
N8 C9 C32 116.9(3) . . ?
C10 C9 C32 121.1(3) . . ?
N1 C10 C11 119.1(3) . . ?
N1 C10 C9 118.8(3) . . ?
C11 C10 C9 122.2(3) . . ?
C12 C11 C10 122.7(3) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
O1 C12 C11 120.7(3) . . ?
O1 C12 C13 114.9(3) . . ?
C11 C12 C13 124.5(3) . . ?
C14 C13 C18 117.4(3) . . ?
C14 C13 C12 121.2(3) . . ?
C18 C13 C12 121.4(3) . . ?
C15 C14 C13 121.7(3) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 N19 120.9(3) . . ?
C17 C16 C15 117.8(3) . . ?
N19 C16 C15 121.2(3) . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C25 C20 C21 118.6(3) . . ?
C25 C20 N19 120.7(3) . . ?
C21 C20 N19 120.7(3) . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 119.5(3) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.7(3) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C20 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
C27 C26 C31 118.3(3) . . ?
C27 C26 N19 121.6(3) . . ?
C31 C26 N19 120.1(3) . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 120.8(3) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C30 C29 C28 119.3(3) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C29 C30 C31 119.8(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C26 121.3(3) . . ?
C30 C31 H31 119.3 . . ?
C26 C31 H31 119.3 . . ?
C33 C32 C37 119.2(3) . . ?
C33 C32 C9 122.7(3) . . ?
C37 C32 C9 118.0(3) . . ?
C34 C33 C32 120.7(3) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 120.1(4) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 120.2(4) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C37 120.1(3) . . ?
C35 C36 H36 120 . . ?
C37 C36 H36 120 . . ?
C32 C37 C36 119.6(3) . . ?
C32 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.130 0.038 0.250 335 72 ' '
2 -0.121 -0.039 0.750 335 72 ' '
_platon_squeeze_details          
;
;


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
