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

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

data_ER1006_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1440668'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H24 B N O2'
_chemical_formula_weight         261.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.8539(9)
_cell_length_b                   7.8160(5)
_cell_length_c                   15.2430(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.8630(10)
_cell_angle_gamma                90
_cell_volume                     1485.22(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7430
_cell_measurement_theta_min      2.6441
_cell_measurement_theta_max      32.5864

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7043
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed X-ray tube'
_diffrn_measurement_device_type  'bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20605
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.660
_diffrn_reflns_theta_max         33.197
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5426
_reflns_number_gt                4414
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       APEX2
_computing_cell_refinement       APEX2
_computing_data_reduction        Saint
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²+0.2503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5426
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11299(5) 0.62328(8) 0.52971(5) 0.02608(14) Uani 1 1 d . . . . .
H1 H 0.1631 0.6952 0.5502 0.039 Uiso 1 1 calc R U . . .
O2 O 0.04704(5) 0.40293(8) 0.41079(5) 0.02658(14) Uani 1 1 d . . . . .
H2 H 0.0023 0.3966 0.4342 0.040 Uiso 1 1 calc R U . . .
N1 N 0.28679(5) 0.79493(8) 0.54440(5) 0.01807(13) Uani 1 1 d . . . . .
C1 C 0.20767(6) 0.56861(9) 0.42105(5) 0.01847(14) Uani 1 1 d . . . . .
C2 C 0.28708(6) 0.69499(10) 0.46363(5) 0.01834(14) Uani 1 1 d . . . . .
C6 C 0.20799(7) 0.47232(11) 0.34339(6) 0.02363(16) Uani 1 1 d . . . . .
H6 H 0.1547 0.3869 0.3141 0.028 Uiso 1 1 calc R U . . .
C12 C 0.37802(6) 0.75205(10) 0.64275(6) 0.02240(15) Uani 1 1 d . . . . .
C7 C 0.25397(7) 0.98052(10) 0.51979(6) 0.02245(15) Uani 1 1 d . . . . .
C3 C 0.36351(7) 0.72066(11) 0.42783(6) 0.02570(17) Uani 1 1 d . . . . .
H3 H 0.4172 0.8057 0.4565 0.031 Uiso 1 1 calc R U . . .
C5 C 0.28388(8) 0.49829(12) 0.30826(6) 0.02909(18) Uani 1 1 d . . . . .
H5 H 0.2826 0.4314 0.2557 0.035 Uiso 1 1 calc R U . . .
C8 C 0.14631(7) 0.98399(12) 0.42846(7) 0.02933(18) Uani 1 1 d . . . . .
H8A H 0.1560 0.9391 0.3728 0.044 Uiso 1 1 calc R U . . .
H8B H 0.1200 1.1020 0.4149 0.044 Uiso 1 1 calc R U . . .
H8C H 0.0942 0.9131 0.4393 0.044 Uiso 1 1 calc R U . . .
C4 C 0.36163(7) 0.62294(12) 0.35072(7) 0.02986(19) Uani 1 1 d . . . . .
H4 H 0.4139 0.6418 0.3271 0.036 Uiso 1 1 calc R U . . .
C13 C 0.37702(8) 0.55784(11) 0.65831(7) 0.03044(19) Uani 1 1 d . . . . .
H13A H 0.3060 0.5230 0.6511 0.046 Uiso 1 1 calc R U . . .
H13B H 0.4311 0.5286 0.7239 0.046 Uiso 1 1 calc R U . . .
H13C H 0.3933 0.4981 0.6099 0.046 Uiso 1 1 calc R U . . .
C11 C 0.35488(8) 0.84182(12) 0.72115(6) 0.02968(18) Uani 1 1 d . . . . .
H11A H 0.2920 0.7869 0.7241 0.036 Uiso 1 1 calc R U . . .
H11B H 0.4171 0.8256 0.7853 0.036 Uiso 1 1 calc R U . . .
C00F C 0.23674(8) 1.05639(12) 0.60487(7) 0.02984(19) Uani 1 1 d . . . . .
H00A H 0.2215 1.1802 0.5932 0.036 Uiso 1 1 calc R U . . .
H00B H 0.1733 1.0016 0.6068 0.036 Uiso 1 1 calc R U . . .
C14 C 0.49175(7) 0.79848(13) 0.65618(7) 0.03162(19) Uani 1 1 d . . . . .
H14A H 0.5079 0.7355 0.6086 0.047 Uiso 1 1 calc R U . . .
H14B H 0.5440 0.7678 0.7223 0.047 Uiso 1 1 calc R U . . .
H14C H 0.4957 0.9217 0.6462 0.047 Uiso 1 1 calc R U . . .
C9 C 0.33216(8) 1.09472(12) 0.49874(8) 0.0328(2) Uani 1 1 d . . . . .
H9A H 0.4026 1.0937 0.5552 0.049 Uiso 1 1 calc R U . . .
H9B H 0.3046 1.2121 0.4861 0.049 Uiso 1 1 calc R U . . .
H9C H 0.3390 1.0509 0.4415 0.049 Uiso 1 1 calc R U . . .
C10 C 0.33303(8) 1.03208(13) 0.70302(7) 0.0324(2) Uani 1 1 d . . . . .
H10A H 0.3966 1.0900 0.7030 0.039 Uiso 1 1 calc R U . . .
H10B H 0.3182 1.0829 0.7554 0.039 Uiso 1 1 calc R U . . .
B1 B 0.11797(7) 0.52977(11) 0.45591(6) 0.01986(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.3682(10) . ?
O1 H1 0.8400 . ?
O2 B1 1.3535(10) . ?
O2 H2 0.8400 . ?
N1 C2 1.4595(10) . ?
N1 C7 1.5175(10) . ?
N1 C12 1.5179(10) . ?
C1 C6 1.4044(11) . ?
C1 C2 1.4087(11) . ?
C1 B1 1.5794(11) . ?
C2 C3 1.4013(11) . ?
C6 C5 1.3873(12) . ?
C6 H6 0.9500 . ?
C12 C11 1.5354(12) . ?
C12 C13 1.5374(12) . ?
C12 C14 1.5410(12) . ?
C7 C8 1.5336(12) . ?
C7 C00F 1.5364(12) . ?
C7 C9 1.5415(13) . ?
C3 C4 1.3923(12) . ?
C3 H3 0.9500 . ?
C5 C4 1.3857(14) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C4 H4 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C11 C10 1.5186(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C00F C10 1.5209(13) . ?
C00F H00A 0.9900 . ?
C00F H00B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
B1 O1 H1 109.5 . . ?
B1 O2 H2 109.5 . . ?
C2 N1 C7 114.45(6) . . ?
C2 N1 C12 114.05(6) . . ?
C7 N1 C12 119.06(6) . . ?
C6 C1 C2 118.37(7) . . ?
C6 C1 B1 118.22(7) . . ?
C2 C1 B1 123.41(7) . . ?
C3 C2 C1 119.47(7) . . ?
C3 C2 N1 122.17(7) . . ?
C1 C2 N1 118.36(6) . . ?
C5 C6 C1 121.91(8) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
N1 C12 C11 107.53(7) . . ?
N1 C12 C13 108.10(6) . . ?
C11 C12 C13 108.19(7) . . ?
N1 C12 C14 116.21(7) . . ?
C11 C12 C14 109.72(7) . . ?
C13 C12 C14 106.83(7) . . ?
N1 C7 C8 108.01(6) . . ?
N1 C7 C00F 107.49(7) . . ?
C8 C7 C00F 108.16(7) . . ?
N1 C7 C9 116.29(7) . . ?
C8 C7 C9 107.11(7) . . ?
C00F C7 C9 109.53(7) . . ?
C4 C3 C2 120.74(8) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C4 C5 C6 119.22(8) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C4 C3 120.30(8) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C11 C12 113.49(7) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C10 C00F C7 112.93(7) . . ?
C10 C00F H00A 109.0 . . ?
C7 C00F H00A 109.0 . . ?
C10 C00F H00B 109.0 . . ?
C7 C00F H00B 109.0 . . ?
H00A C00F H00B 107.8 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C00F 108.72(7) . . ?
C11 C10 H10A 109.9 . . ?
C00F C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C00F C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O2 B1 O1 121.55(7) . . ?
O2 B1 C1 118.24(7) . . ?
O1 B1 C1 120.21(7) . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.044

_shelxl_version_number           2014/6

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_ER1006_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1440669'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H26 B F2 N O'
_chemical_formula_weight         297.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.6884(7)
_cell_length_b                   13.7157(12)
_cell_length_c                   15.1094(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.4350(10)
_cell_angle_gamma                90
_cell_volume                     1576.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6209
_cell_measurement_theta_min      2.7256
_cell_measurement_theta_max      31.9857

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed X-ray tube'
_diffrn_measurement_device_type  'bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22164
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.015
_diffrn_reflns_theta_max         33.173
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5750
_reflns_number_gt                4511
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       APEX2
_computing_cell_refinement       APEX2
_computing_data_reduction        Saint
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+0.2882P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5750
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.29632(9) 0.77698(5) 0.85316(5) 0.03360(16) Uani 1 1 d . . . . .
F2 F 0.54158(11) 0.69433(5) 0.91291(4) 0.03838(18) Uani 1 1 d . . . . .
O1 O 0.56886(10) 0.82816(6) 0.81763(5) 0.02670(16) Uani 1 1 d . . . . .
N1 N 0.62568(9) 0.76133(5) 0.66097(5) 0.01513(14) Uani 1 1 d . . . . .
C6 C 0.51046(11) 0.67617(6) 0.67075(6) 0.01640(15) Uani 1 1 d . . . . .
C1 C 0.43755(11) 0.66946(6) 0.75032(5) 0.01661(15) Uani 1 1 d . . . . .
C2 C 0.33273(12) 0.58680(7) 0.75840(6) 0.02179(18) Uani 1 1 d . . . . .
H2 H 0.2810 0.5792 0.8114 0.026 Uiso 1 1 calc R U . . .
C7 C 0.54984(12) 0.83754(6) 0.58919(6) 0.01817(16) Uani 1 1 d . . . . .
C12 C 0.82646(11) 0.73736(7) 0.67090(6) 0.02076(17) Uani 1 1 d . . . . .
C5 C 0.47998(13) 0.60643(7) 0.60314(6) 0.02324(18) Uani 1 1 d . . . . .
H5 H 0.5306 0.6137 0.5498 0.028 Uiso 1 1 calc R U . . .
C3 C 0.30152(13) 0.51593(7) 0.69252(7) 0.0264(2) Uani 1 1 d . . . . .
H3 H 0.2306 0.4609 0.7008 0.032 Uiso 1 1 calc R U . . .
C00C C 0.66483(14) 0.92844(7) 0.60813(7) 0.0265(2) Uani 1 1 d . . . . .
H00A H 0.6271 0.9777 0.5613 0.032 Uiso 1 1 calc R U . . .
H00B H 0.6451 0.9563 0.6663 0.032 Uiso 1 1 calc R U . . .
C9 C 0.54276(14) 0.80385(8) 0.49268(6) 0.02520(19) Uani 1 1 d . . . . .
H9A H 0.4917 0.8555 0.4522 0.038 Uiso 1 1 calc R U . . .
H9B H 0.4700 0.7451 0.4829 0.038 Uiso 1 1 calc R U . . .
H9C H 0.6620 0.7893 0.4809 0.038 Uiso 1 1 calc R U . . .
C4 C 0.37488(14) 0.52620(8) 0.61441(7) 0.0282(2) Uani 1 1 d . . . . .
H4 H 0.3533 0.4784 0.5686 0.034 Uiso 1 1 calc R U . . .
C8 C 0.36238(13) 0.86025(8) 0.60612(7) 0.0266(2) Uani 1 1 d . . . . .
H8A H 0.3157 0.9153 0.5686 0.040 Uiso 1 1 calc R U . . .
H8B H 0.3639 0.8771 0.6693 0.040 Uiso 1 1 calc R U . . .
H8C H 0.2876 0.8029 0.5913 0.040 Uiso 1 1 calc R U . . .
C14 C 0.88291(14) 0.68111(8) 0.59249(7) 0.0277(2) Uani 1 1 d . . . . .
H14A H 0.8670 0.7223 0.5389 0.042 Uiso 1 1 calc R U . . .
H14B H 0.8109 0.6222 0.5812 0.042 Uiso 1 1 calc R U . . .
H14C H 1.0070 0.6627 0.6071 0.042 Uiso 1 1 calc R U . . .
C11 C 0.92120(13) 0.83560(9) 0.68457(7) 0.0288(2) Uani 1 1 d . . . . .
H11A H 0.9010 0.8632 0.7427 0.035 Uiso 1 1 calc R U . . .
H11B H 1.0492 0.8247 0.6873 0.035 Uiso 1 1 calc R U . . .
C13 C 0.86899(14) 0.67609(9) 0.75583(7) 0.0304(2) Uani 1 1 d . . . . .
H13A H 0.9968 0.6707 0.7720 0.046 Uiso 1 1 calc R U . . .
H13B H 0.8182 0.6109 0.7452 0.046 Uiso 1 1 calc R U . . .
H13C H 0.8193 0.7074 0.8048 0.046 Uiso 1 1 calc R U . . .
C10 C 0.86115(15) 0.90944(9) 0.61089(8) 0.0324(2) Uani 1 1 d . . . . .
H10A H 0.8839 0.8837 0.5525 0.039 Uiso 1 1 calc R U . . .
H10B H 0.9275 0.9711 0.6229 0.039 Uiso 1 1 calc R U . . .
C15 C 0.63258(15) 0.89112(9) 0.88902(7) 0.0321(2) Uani 1 1 d . . . . .
H15A H 0.5339 0.9261 0.9086 0.048 Uiso 1 1 calc R U . . .
H15B H 0.7146 0.9381 0.8690 0.048 Uiso 1 1 calc R U . . .
H15C H 0.6935 0.8528 0.9389 0.048 Uiso 1 1 calc R U . . .
B1 B 0.46268(13) 0.74407(8) 0.83586(6) 0.01961(18) Uani 1 1 d . . . . .
H1 H 0.6195(18) 0.7951(10) 0.7157(9) 0.028(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.4164(12) . ?
F2 B1 1.4076(12) . ?
O1 C15 1.4122(12) . ?
O1 B1 1.4624(13) . ?
N1 C6 1.4864(11) . ?
N1 C7 1.5567(11) . ?
N1 C12 1.5638(11) . ?
N1 H1 0.956(14) . ?
C6 C5 1.3939(12) . ?
C6 C1 1.4021(11) . ?
C1 C2 1.4067(12) . ?
C1 B1 1.6376(13) . ?
C2 C3 1.3868(14) . ?
C2 H2 0.9500 . ?
C7 C9 1.5230(13) . ?
C7 C00C 1.5309(14) . ?
C7 C8 1.5323(13) . ?
C12 C13 1.5287(13) . ?
C12 C14 1.5290(14) . ?
C12 C11 1.5312(15) . ?
C5 C4 1.3904(14) . ?
C5 H5 0.9500 . ?
C3 C4 1.3879(15) . ?
C3 H3 0.9500 . ?
C00C C10 1.5262(16) . ?
C00C H00A 0.9900 . ?
C00C H00B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C4 H4 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C11 C10 1.5256(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 B1 118.62(8) . . ?
C6 N1 C7 115.42(6) . . ?
C6 N1 C12 114.80(7) . . ?
C7 N1 C12 118.14(6) . . ?
C6 N1 H1 100.9(8) . . ?
C7 N1 H1 102.5(8) . . ?
C12 N1 H1 101.1(8) . . ?
C5 C6 C1 122.55(8) . . ?
C5 C6 N1 120.33(8) . . ?
C1 C6 N1 117.12(7) . . ?
C6 C1 C2 115.69(8) . . ?
C6 C1 B1 128.32(8) . . ?
C2 C1 B1 115.97(7) . . ?
C3 C2 C1 122.93(9) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C9 C7 C00C 111.38(8) . . ?
C9 C7 C8 108.61(8) . . ?
C00C C7 C8 109.56(8) . . ?
C9 C7 N1 114.86(7) . . ?
C00C C7 N1 105.64(7) . . ?
C8 C7 N1 106.59(7) . . ?
C13 C12 C14 108.84(8) . . ?
C13 C12 C11 109.36(8) . . ?
C14 C12 C11 111.41(8) . . ?
C13 C12 N1 106.42(7) . . ?
C14 C12 N1 114.84(7) . . ?
C11 C12 N1 105.74(8) . . ?
C4 C5 C6 119.44(9) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C2 C3 C4 119.35(9) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C10 C00C C7 114.06(9) . . ?
C10 C00C H00A 108.7 . . ?
C7 C00C H00A 108.7 . . ?
C10 C00C H00B 108.7 . . ?
C7 C00C H00B 108.7 . . ?
H00A C00C H00B 107.6 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C4 C5 120.03(9) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C11 C12 113.49(8) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C10 C00C 109.00(8) . . ?
C11 C10 H10A 109.9 . . ?
C00C C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C00C C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F2 B1 F1 107.04(8) . . ?
F2 B1 O1 110.69(8) . . ?
F1 B1 O1 109.12(8) . . ?
F2 B1 C1 109.67(8) . . ?
F1 B1 C1 109.85(8) . . ?
O1 B1 C1 110.40(7) . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.050

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_ER1007_a
_database_code_depnum_ccdc_archive 'CCDC 1440670'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H23 B F3 N'
_chemical_formula_weight         285.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.8666(9)
_cell_length_b                   7.6330(5)
_cell_length_c                   14.4543(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.5310(10)
_cell_angle_gamma                90
_cell_volume                     1480.06(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4538
_cell_measurement_theta_min      2.8237
_cell_measurement_theta_max      32.0895

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6940
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed X-ray tube'
_diffrn_measurement_device_type  'bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20569
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.518
_diffrn_reflns_theta_max         33.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5400
_reflns_number_gt                3950
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       APEX2
_computing_cell_refinement       APEX2
_computing_data_reduction        Saint
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5400
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F3 F 0.14404(5) 0.65328(9) 0.56514(5) 0.02535(16) Uani 1 1 d . . . . .
F1 F 0.17822(5) 0.59542(10) 0.42784(5) 0.02969(18) Uani 1 1 d . . . . .
F2 F 0.26211(6) 0.81226(9) 0.54014(6) 0.03206(18) Uani 1 1 d . . . . .
N1 N 0.22033(6) 0.38050(10) 0.69342(6) 0.01367(16) Uani 1 1 d . . . . .
C1 C 0.30871(7) 0.50424(12) 0.59806(7) 0.01532(18) Uani 1 1 d . . . . .
C2 C 0.30825(7) 0.38136(13) 0.66960(7) 0.01578(18) Uani 1 1 d . . . . .
C6 C 0.39369(8) 0.50305(14) 0.57883(8) 0.0200(2) Uani 1 1 d . . . . .
H6 H 0.3973 0.5842 0.5307 0.024 Uiso 1 1 calc R U . . .
C7 C 0.14755(8) 0.22178(13) 0.64885(8) 0.0201(2) Uani 1 1 d . . . . .
C13 C 0.24059(7) 0.44843(13) 0.80301(7) 0.01586(18) Uani 1 1 d . . . . .
C12 C 0.13784(7) 0.48350(13) 0.79931(8) 0.0188(2) Uani 1 1 d . . . . .
H12A H 0.1464 0.5196 0.8684 0.023 Uiso 1 1 calc R U . . .
H12B H 0.1066 0.5824 0.7519 0.023 Uiso 1 1 calc R U . . .
C5 C 0.47223(8) 0.38857(17) 0.62712(9) 0.0260(2) Uani 1 1 d . . . . .
H5 H 0.5284 0.3918 0.6120 0.031 Uiso 1 1 calc R U . . .
C11 C 0.06793(8) 0.32694(14) 0.76483(8) 0.0224(2) Uani 1 1 d . . . . .
H11A H 0.0032 0.3582 0.7645 0.027 Uiso 1 1 calc R U . . .
H11B H 0.0969 0.2284 0.8132 0.027 Uiso 1 1 calc R U . . .
C3 C 0.38631(8) 0.26470(15) 0.71892(9) 0.0255(2) Uani 1 1 d . . . . .
H3 H 0.3832 0.1825 0.7668 0.031 Uiso 1 1 calc R U . . .
C14 C 0.29716(9) 0.62096(15) 0.81808(8) 0.0248(2) Uani 1 1 d . . . . .
H14A H 0.2969 0.6831 0.8773 0.037 Uiso 1 1 calc R U . . .
H14B H 0.2648 0.6936 0.7566 0.037 Uiso 1 1 calc R U . . .
H14C H 0.3661 0.5969 0.8300 0.037 Uiso 1 1 calc R U . . .
C15 C 0.30141(8) 0.32519(16) 0.89065(8) 0.0257(2) Uani 1 1 d . . . . .
H15A H 0.3644 0.2973 0.8876 0.039 Uiso 1 1 calc R U . . .
H15B H 0.2637 0.2170 0.8845 0.039 Uiso 1 1 calc R U . . .
H15C H 0.3152 0.3819 0.9562 0.039 Uiso 1 1 calc R U . . .
C10 C 0.05201(8) 0.27179(16) 0.65749(8) 0.0237(2) Uani 1 1 d . . . . .
H10A H 0.0195 0.3693 0.6095 0.028 Uiso 1 1 calc R U . . .
H10B H 0.0059 0.1706 0.6358 0.028 Uiso 1 1 calc R U . . .
C8 C 0.12548(10) 0.20866(16) 0.53554(9) 0.0292(3) Uani 1 1 d . . . . .
H8A H 0.1862 0.1741 0.5294 0.044 Uiso 1 1 calc R U . . .
H8B H 0.1027 0.3227 0.5025 0.044 Uiso 1 1 calc R U . . .
H8C H 0.0734 0.1208 0.5020 0.044 Uiso 1 1 calc R U . . .
C4 C 0.46877(9) 0.26942(17) 0.69747(10) 0.0309(3) Uani 1 1 d . . . . .
H4 H 0.5227 0.1909 0.7311 0.037 Uiso 1 1 calc R U . . .
C9 C 0.18981(11) 0.04776(15) 0.70092(10) 0.0311(3) Uani 1 1 d . . . . .
H9A H 0.2002 0.0525 0.7726 0.047 Uiso 1 1 calc R U . . .
H9B H 0.2536 0.0253 0.6983 0.047 Uiso 1 1 calc R U . . .
H9C H 0.1429 -0.0466 0.6654 0.047 Uiso 1 1 calc R U . . .
B1 B 0.22217(9) 0.64447(15) 0.53179(9) 0.0191(2) Uani 1 1 d . . . . .
H1 H 0.1839(10) 0.4730(17) 0.6540(11) 0.021(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 B1 1.4383(12) . ?
F1 B1 1.4066(13) . ?
F2 B1 1.3949(13) . ?
N1 C2 1.4883(11) . ?
N1 C7 1.5661(13) . ?
N1 C13 1.5676(12) . ?
N1 H1 0.922(14) . ?
C1 C2 1.3982(13) . ?
C1 C6 1.4059(13) . ?
C1 B1 1.6298(15) . ?
C2 C3 1.3909(14) . ?
C6 C5 1.3826(16) . ?
C6 H6 0.9500 . ?
C7 C9 1.5224(16) . ?
C7 C10 1.5270(15) . ?
C7 C8 1.5288(15) . ?
C13 C15 1.5231(14) . ?
C13 C14 1.5268(14) . ?
C13 C12 1.5289(13) . ?
C12 C11 1.5199(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C5 C4 1.3817(17) . ?
C5 H5 0.9500 . ?
C11 C10 1.5244(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 C4 1.3885(15) . ?
C3 H3 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C4 H4 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C7 115.35(7) . . ?
C2 N1 C13 115.27(7) . . ?
C7 N1 C13 117.99(7) . . ?
C2 N1 H1 101.2(8) . . ?
C7 N1 H1 102.7(8) . . ?
C13 N1 H1 100.2(8) . . ?
C2 C1 C6 115.67(9) . . ?
C2 C1 B1 128.39(8) . . ?
C6 C1 B1 115.91(8) . . ?
C3 C2 C1 122.66(9) . . ?
C3 C2 N1 120.03(8) . . ?
C1 C2 N1 117.30(8) . . ?
C5 C6 C1 122.66(9) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
C9 C7 C10 112.20(9) . . ?
C9 C7 C8 108.95(9) . . ?
C10 C7 C8 109.04(9) . . ?
C9 C7 N1 114.01(9) . . ?
C10 C7 N1 105.97(8) . . ?
C8 C7 N1 106.41(8) . . ?
C15 C13 C14 108.72(9) . . ?
C15 C13 C12 111.30(8) . . ?
C14 C13 C12 109.55(8) . . ?
C15 C13 N1 115.01(8) . . ?
C14 C13 N1 106.48(7) . . ?
C12 C13 N1 105.58(7) . . ?
C11 C12 C13 113.92(8) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C4 C5 C6 119.76(10) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C12 C11 C10 109.58(8) . . ?
C12 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C4 C3 C2 119.39(10) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C10 C7 114.23(9) . . ?
C11 C10 H10A 108.7 . . ?
C7 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C7 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C4 C3 119.87(10) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F2 B1 F1 108.74(8) . . ?
F2 B1 F3 107.65(8) . . ?
F1 B1 F3 107.46(9) . . ?
F2 B1 C1 110.70(9) . . ?
F1 B1 C1 109.79(8) . . ?
F3 B1 C1 112.37(8) . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

