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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sh3172

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 B Br F2 N2'
_chemical_formula_sum            'C11 H10 B Br F2 N2'
_chemical_formula_weight         298.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   12.4626(6)
_cell_length_b                   6.6321(3)
_cell_length_c                   13.8280(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1142.93(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3635
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.56

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    3.598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5035
_exptl_absorpt_correction_T_max  0.8350
_exptl_absorpt_process_details   'SADABS, Bruker-AXS 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12805
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         28.91
_reflns_number_total             1612
_reflns_number_gt                1278
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0872P)²+4.5778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1612
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1797
_refine_ls_wR_factor_gt          0.1703
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.93534(6) 0.2500 1.30579(5) 0.0342(3) Uani 1 2 d S . .
B B 0.8327(5) 0.2500 1.0858(5) 0.0173(12) Uani 1 2 d S . .
F F 0.7866(2) 0.0788(4) 1.12555(18) 0.0287(6) Uani 1 1 d . . .
N1 N 0.8168(4) 0.2500 0.9738(3) 0.0179(10) Uani 1 2 d S . .
N2 N 0.9563(4) 0.2500 1.1027(4) 0.0167(10) Uani 1 2 d S . .
C1 C 0.7226(5) 0.2500 0.9275(5) 0.0233(13) Uani 1 2 d S . .
C2 C 0.7409(5) 0.2500 0.8268(5) 0.0260(13) Uani 1 2 d S . .
H2 H 0.6874 0.2500 0.7779 0.031 Uiso 1 2 calc SR . .
C3 C 0.8506(5) 0.2500 0.8123(4) 0.0209(12) Uani 1 2 d S . .
C4 C 0.8986(4) 0.2500 0.9053(4) 0.0177(11) Uani 1 2 d S . .
C5 C 1.0039(4) 0.2500 0.9337(4) 0.0162(11) Uani 1 2 d S . .
H5 H 1.0585 0.2500 0.8857 0.019 Uiso 1 2 calc SR . .
C6 C 1.0334(5) 0.2500 1.0316(4) 0.0184(11) Uani 1 2 d S . .
C7 C 1.1360(5) 0.2500 1.0751(5) 0.0229(12) Uani 1 2 d S . .
H7 H 1.2032 0.2500 1.0425 0.028 Uiso 1 2 calc SR . .
C8 C 1.1199(5) 0.2500 1.1746(5) 0.0222(12) Uani 1 2 d S . .
H8 H 1.1735 0.2500 1.2234 0.027 Uiso 1 2 calc SR . .
C9 C 1.0088(5) 0.2500 1.1883(4) 0.0207(12) Uani 1 2 d S . .
C10 C 0.6147(4) 0.2500 0.9780(4) 0.0171(11) Uani 1 2 d S . .
H10A H 0.6212 0.3182 1.0406 0.026 Uiso 0.50 1 calc PR . .
H10B H 0.5910 0.1107 0.9881 0.026 Uiso 0.50 1 calc PR . .
H10C H 0.5620 0.3211 0.9378 0.026 Uiso 0.50 1 calc PR . .
C11 C 0.9062(6) 0.2500 0.7167(5) 0.0273(14) Uani 1 2 d S . .
H11A H 0.8663 0.3348 0.6712 0.041 Uiso 0.50 1 calc PR . .
H11B H 0.9098 0.1119 0.6917 0.041 Uiso 0.50 1 calc PR . .
H11C H 0.9790 0.3033 0.7244 0.041 Uiso 0.50 1 calc PR . .


_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
Br C9 1.865(6) . ?
B F 1.387(4) . ?
B F 1.387(4) 7_565 ?
B N2 1.558(7) . ?
B N1 1.560(8) . ?
N1 C1 1.338(7) . ?
N1 C4 1.392(7) . ?
N2 C9 1.352(7) . ?
N2 C6 1.375(8) . ?
C1 C2 1.410(9) . ?
C1 C10 1.516(7) . ?
C2 C3 1.382(9) . ?
C3 C4 1.419(8) . ?
C3 C11 1.492(8) . ?
C4 C5 1.370(8) . ?
C5 C6 1.404(8) . ?
C6 C7 1.413(8) . ?
C7 C8 1.390(9) . ?
C8 C9 1.398(9) . ?

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
F B F 110.0(5) . 7_565 ?
F B N2 110.5(3) . . ?
F B N2 110.5(3) 7_565 . ?
F B N1 109.9(3) . . ?
F B N1 109.9(3) 7_565 . ?
N2 B N1 105.9(5) . . ?
C1 N1 C4 108.5(5) . . ?
C1 N1 B 125.9(5) . . ?
C4 N1 B 125.6(5) . . ?
C9 N2 C6 106.7(5) . . ?
C9 N2 B 127.6(5) . . ?
C6 N2 B 125.7(5) . . ?
N1 C1 C2 109.3(5) . . ?
N1 C1 C10 123.9(6) . . ?
C2 C1 C10 126.7(5) . . ?
C3 C2 C1 107.7(5) . . ?
C2 C3 C4 106.5(5) . . ?
C2 C3 C11 126.0(6) . . ?
C4 C3 C11 127.4(6) . . ?
C5 C4 N1 120.5(5) . . ?
C5 C4 C3 131.5(5) . . ?
N1 C4 C3 108.0(5) . . ?
C4 C5 C6 121.8(5) . . ?
N2 C6 C5 120.5(5) . . ?
N2 C6 C7 109.2(5) . . ?
C5 C6 C7 130.3(6) . . ?
C8 C7 C6 106.8(5) . . ?
C7 C8 C9 106.1(5) . . ?
N2 C9 C8 111.1(5) . . ?
N2 C9 Br 121.7(5) . . ?
C8 C9 Br 127.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.91
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.670
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.234
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_database_code_depnum_ccdc_archive 'CCDC 1010897'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sh3122

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 B F2 I N2'
_chemical_formula_sum            'C11 H10 B F2 I N2'
_chemical_formula_weight         345.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3108(10)
_cell_length_b                   8.5603(12)
_cell_length_c                   10.3487(15)
_cell_angle_alpha                93.027(7)
_cell_angle_beta                 95.908(6)
_cell_angle_gamma                113.336(6)
_cell_volume                     588.40(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    132(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      39.46

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.952
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    2.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3506
_exptl_absorpt_correction_T_max  0.8624
_exptl_absorpt_process_details   'SADABS, BrukerAXS 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      132(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20504
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         39.68
_reflns_number_total             6866
_reflns_number_gt                5901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0278P)²+0.2116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6866
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0645
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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
I1 I 1.162314(14) 0.335668(11) 0.469206(8) 0.02466(3) Uani 1 1 d . . .
B1 B 0.82044(18) 0.22544(15) -0.06190(13) 0.01450(18) Uani 1 1 d . . .
F1 F 0.72259(12) 0.33530(10) -0.05571(8) 0.01894(13) Uani 1 1 d . . .
F2 F 0.98927(11) 0.30017(10) -0.12620(8) 0.01919(13) Uani 1 1 d . . .
N2 N 0.67974(14) 0.04933(12) -0.13714(10) 0.01454(15) Uani 1 1 d . . .
N1 N 0.88227(14) 0.18862(12) 0.07714(10) 0.01442(15) Uani 1 1 d . . .
C1 C 0.98593(17) 0.30551(14) 0.18000(12) 0.01669(17) Uani 1 1 d . . .
C2 C 1.01843(17) 0.21998(15) 0.28537(12) 0.01684(18) Uani 1 1 d . . .
C3 C 0.93236(18) 0.04469(15) 0.24561(12) 0.01664(17) Uani 1 1 d . . .
C4 C 0.84698(16) 0.02745(14) 0.11546(11) 0.01459(16) Uani 1 1 d . . .
C5 C 0.73506(16) -0.11990(14) 0.02884(11) 0.01464(16) Uani 1 1 d . . .
C6 C 0.65343(16) -0.10925(13) -0.09318(11) 0.01387(16) Uani 1 1 d . . .
C7 C 0.52996(17) -0.24125(14) -0.19355(11) 0.01571(17) Uani 1 1 d . . .
C8 C 0.48329(19) -0.15960(16) -0.29446(12) 0.01838(18) Uani 1 1 d . . .
C9 C 0.57836(18) 0.01955(15) -0.25735(12) 0.01707(18) Uani 1 1 d . . .
C10 C 0.4650(2) -0.42897(16) -0.18667(14) 0.0205(2) Uani 1 1 d . . .
C11 C 0.5758(3) 0.15874(19) -0.33654(14) 0.0258(3) Uani 1 1 d . . .
H4 H 0.399(3) -0.213(3) -0.372(2) 0.025(5) Uiso 1 1 d . . .
H1 H 1.027(3) 0.421(3) 0.174(2) 0.024(5) Uiso 1 1 d . . .
H3 H 0.717(3) -0.231(3) 0.059(2) 0.019(5) Uiso 1 1 d . . .
H2 H 0.927(3) -0.047(3) 0.294(2) 0.018(4) Uiso 1 1 d . . .
H6 H 0.477(4) -0.484(3) -0.264(3) 0.040(7) Uiso 1 1 d . . .
H9 H 0.479(4) 0.107(4) -0.407(3) 0.048(7) Uiso 1 1 d . . .
H5 H 0.550(4) -0.452(4) -0.119(3) 0.047(7) Uiso 1 1 d . . .
H10 H 0.566(4) 0.249(4) -0.286(3) 0.052(8) Uiso 1 1 d . . .
H7 H 0.330(4) -0.483(3) -0.165(3) 0.041(7) Uiso 1 1 d . . .
H8 H 0.691(5) 0.207(4) -0.367(3) 0.051(8) 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
I1 C2 2.0664(12) . ?
B1 F1 1.3915(14) . ?
B1 F2 1.4015(15) . ?
B1 N1 1.5495(16) . ?
B1 N2 1.5555(16) . ?
N2 C9 1.3376(15) . ?
N2 C6 1.4011(14) . ?
N1 C1 1.3525(16) . ?
N1 C4 1.3871(14) . ?
C1 C2 1.3966(17) . ?
C2 C3 1.3965(17) . ?
C3 C4 1.3994(16) . ?
C4 C5 1.4058(16) . ?
C5 C6 1.3634(16) . ?
C6 C7 1.4303(16) . ?
C7 C8 1.3741(17) . ?
C7 C10 1.4924(17) . ?
C8 C9 1.4216(17) . ?
C9 C11 1.4864(17) . ?

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
F1 B1 F2 108.81(9) . . ?
F1 B1 N1 110.44(10) . . ?
F2 B1 N1 110.86(9) . . ?
F1 B1 N2 111.19(9) . . ?
F2 B1 N2 109.18(10) . . ?
N1 B1 N2 106.35(8) . . ?
C9 N2 C6 107.65(10) . . ?
C9 N2 B1 127.56(9) . . ?
C6 N2 B1 124.53(9) . . ?
C1 N1 C4 108.12(9) . . ?
C1 N1 B1 126.76(9) . . ?
C4 N1 B1 125.06(9) . . ?
N1 C1 C2 108.72(10) . . ?
C3 C2 C1 108.23(10) . . ?
C3 C2 I1 126.55(8) . . ?
C1 C2 I1 125.19(9) . . ?
C2 C3 C4 105.95(10) . . ?
N1 C4 C3 108.97(10) . . ?
N1 C4 C5 120.53(10) . . ?
C3 C4 C5 130.47(10) . . ?
C6 C5 C4 121.29(10) . . ?
C5 C6 N2 121.11(10) . . ?
C5 C6 C7 130.30(10) . . ?
N2 C6 C7 108.56(9) . . ?
C8 C7 C6 106.03(10) . . ?
C8 C7 C10 127.94(11) . . ?
C6 C7 C10 126.03(10) . . ?
C7 C8 C9 108.11(11) . . ?
N2 C9 C8 109.64(10) . . ?
N2 C9 C11 122.90(11) . . ?
C8 C9 C11 127.44(12) . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        39.68
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.822
_refine_diff_density_min         -1.498
_refine_diff_density_rms         0.105
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_database_code_depnum_ccdc_archive 'CCDC 1010898'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sh3415

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 B F2 N2 Si'
_chemical_formula_sum            'C16 H19 B F2 N2 Si'
_chemical_formula_weight         316.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   23.5959(3)
_cell_length_b                   11.5341(3)
_cell_length_c                   12.3552(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3362.56(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    9773
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.90

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9540
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_process_details   'SADABS, BrukerAXS 2010'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      163(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27081
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         27.90
_reflns_number_total             7914
_reflns_number_gt                6782
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          Twin

_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)+(0.0498P)²+0.4390P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         7914
_refine_ls_number_parameters     459
_refine_ls_number_restraints     127
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.74137(2) 1.05144(5) 0.50873(5) 0.03096(14) Uani 1 1 d U . .
F1 F 0.59729(5) 0.45106(10) 1.08814(10) 0.0345(3) Uani 1 1 d U . .
F2 F 0.61561(4) 0.28409(11) 0.99665(10) 0.0326(3) Uani 1 1 d U . .
N1 N 0.53123(6) 0.29276(14) 1.10666(13) 0.0206(3) Uani 1 1 d U . .
N2 N 0.53876(6) 0.40401(13) 0.93457(13) 0.0212(3) Uani 1 1 d U . .
B1 B 0.57387(8) 0.3596(2) 1.03194(18) 0.0234(5) Uani 1 1 d U . .
C1 C 0.54298(9) 0.23925(17) 1.20010(17) 0.0253(4) Uani 1 1 d U . .
C2 C 0.49257(9) 0.19050(19) 1.24362(19) 0.0299(5) Uani 1 1 d U . .
C3 C 0.44912(8) 0.21522(17) 1.17528(17) 0.0274(4) Uani 1 1 d U . .
C4 C 0.47294(7) 0.28012(16) 1.08724(16) 0.0227(4) Uani 1 1 d U . .
C5 C 0.44903(7) 0.32774(17) 0.99700(16) 0.0240(4) Uani 1 1 d U . .
C6 C 0.48093(7) 0.38962(17) 0.91989(17) 0.0232(4) Uani 1 1 d U . .
C7 C 0.46475(9) 0.44190(17) 0.82293(17) 0.0269(4) Uani 1 1 d U . .
C8 C 0.51299(9) 0.48847(19) 0.77701(16) 0.0279(5) Uani 1 1 d U . .
C9 C 0.55822(8) 0.46397(16) 0.84654(16) 0.0238(4) Uani 1 1 d U . .
C10 C 0.60053(9) 0.2343(2) 1.2480(2) 0.0350(5) Uani 1 1 d U . .
H5 H 0.6261 0.2844 1.2066 0.052 Uiso 1 1 calc R . .
H6 H 0.6145 0.1543 1.2457 0.052 Uiso 1 1 calc R . .
H7 H 0.5990 0.2608 1.3233 0.052 Uiso 1 1 calc R . .
C11 C 0.38804(10) 0.1839(3) 1.1855(2) 0.0409(6) Uani 1 1 d U . .
C12 C 0.61651(9) 0.49240(17) 0.83213(17) 0.0284(4) Uani 1 1 d U . .
C13 C 0.66503(9) 0.51673(19) 0.81464(17) 0.0322(5) Uani 1 1 d U . .
C14 C 0.75120(9) 0.70094(19) 0.8518(2) 0.0453(5) Uani 1 1 d U . .
H14A H 0.7249 0.7571 0.8198 0.068 Uiso 1 1 calc R . .
H14B H 0.7903 0.7258 0.8383 0.068 Uiso 1 1 calc R . .
H14C H 0.7446 0.6963 0.9300 0.068 Uiso 1 1 calc R . .
C15 C 0.75019(14) 0.5603(3) 0.6415(2) 0.0679(8) Uani 1 1 d U . .
H15A H 0.7402 0.4847 0.6107 0.102 Uiso 1 1 calc R . .
H15B H 0.7900 0.5775 0.6255 0.102 Uiso 1 1 calc R . .
H15C H 0.7260 0.6204 0.6097 0.102 Uiso 1 1 calc R . .
C16 C 0.78610(11) 0.4450(2) 0.8512(3) 0.0662(8) Uani 1 1 d U . .
H16A H 0.7791 0.4410 0.9293 0.099 Uiso 1 1 calc R . .
H16B H 0.8258 0.4654 0.8383 0.099 Uiso 1 1 calc R . .
H16C H 0.7780 0.3695 0.8183 0.099 Uiso 1 1 calc R . .
H1 H 0.4924(9) 0.1586(19) 1.306(2) 0.029(6) Uiso 1 1 d . . .
H2 H 0.4078(8) 0.3187(16) 0.9852(16) 0.021(5) Uiso 1 1 d . . .
H3 H 0.4281(10) 0.4402(19) 0.795(2) 0.039(6) Uiso 1 1 d . . .
H4 H 0.5198(8) 0.5229(17) 0.7086(18) 0.020(5) Uiso 1 1 d . . .
H8 H 0.3815(13) 0.118(3) 1.146(3) 0.091(11) Uiso 1 1 d . . .
H9 H 0.3804(13) 0.150(3) 1.258(3) 0.084(10) Uiso 1 1 d . . .
H10 H 0.3607(12) 0.243(3) 1.186(3) 0.072(10) Uiso 1 1 d . . .
H11 H 0.4969(9) 0.6437(19) -0.038(2) 0.030(6) Uiso 1 1 d . . .
Si2 Si 0.73954(2) 0.55692(6) 0.79016(5) 0.03389(15) Uani 1 1 d U . .
N3 N 0.53703(6) 0.79587(14) 0.16184(14) 0.0201(3) Uani 1 1 d U . .
N4 N 0.54310(6) 0.90882(13) 0.33370(12) 0.0195(3) Uani 1 1 d U . .
B2 B 0.57843(8) 0.8649(2) 0.23617(17) 0.0221(5) Uani 1 1 d U . .
F3 F 0.60046(5) 0.95767(10) 0.17867(10) 0.0328(3) Uani 1 1 d U . .
F4 F 0.62140(4) 0.79302(11) 0.27131(10) 0.0354(3) Uani 1 1 d U . .
C17 C 0.54936(8) 0.74222(17) 0.06905(16) 0.0239(4) Uani 1 1 d U . .
C18 C 0.49971(8) 0.69051(18) 0.02600(17) 0.0260(4) Uani 1 1 d U . .
C19 C 0.45585(7) 0.71384(17) 0.09453(17) 0.0244(4) Uani 1 1 d U . .
C20 C 0.47872(7) 0.78153(16) 0.18156(16) 0.0203(4) Uani 1 1 d U . .
C21 C 0.45413(7) 0.82770(17) 0.27101(15) 0.0211(4) Uani 1 1 d U . .
C22 C 0.48540(7) 0.89211(17) 0.34776(16) 0.0201(4) Uani 1 1 d U . .
C23 C 0.46890(8) 0.94371(17) 0.44519(16) 0.0244(4) Uani 1 1 d U . .
C24 C 0.51674(8) 0.99259(18) 0.49120(16) 0.0249(4) Uani 1 1 d U . .
C25 C 0.56212(8) 0.96973(16) 0.42168(15) 0.0214(4) Uani 1 1 d U . .
C26 C 0.39518(9) 0.6787(2) 0.0828(2) 0.0348(5) Uani 1 1 d U . .
C27 C 0.60703(8) 0.7408(2) 0.0213(2) 0.0353(5) Uani 1 1 d U . .
H15 H 0.6247 0.8170 0.0307 0.053 Uiso 1 1 calc R . .
H16 H 0.6045 0.7226 -0.0560 0.053 Uiso 1 1 calc R . .
H17 H 0.6300 0.6817 0.0577 0.053 Uiso 1 1 calc R . .
C28 C 0.61988(8) 0.99970(17) 0.43903(16) 0.0252(4) Uani 1 1 d U . .
C29 C 0.66811(8) 1.02608(19) 0.46208(17) 0.0302(4) Uani 1 1 d U . .
C30 C 0.75928(9) 0.93074(19) 0.6014(2) 0.0455(6) Uani 1 1 d U . .
H30A H 0.7310 0.9265 0.6593 0.068 Uiso 1 1 calc R . .
H30B H 0.7968 0.9442 0.6330 0.068 Uiso 1 1 calc R . .
H30C H 0.7595 0.8576 0.5610 0.068 Uiso 1 1 calc R . .
C31 C 0.74577(9) 1.19202(19) 0.5803(2) 0.0468(6) Uani 1 1 d U . .
H31A H 0.7327 1.2541 0.5323 0.070 Uiso 1 1 calc R . .
H31B H 0.7851 1.2068 0.6016 0.070 Uiso 1 1 calc R . .
H31C H 0.7218 1.1896 0.6451 0.070 Uiso 1 1 calc R . .
C32 C 0.78903(10) 1.0542(3) 0.3898(2) 0.0688(8) Uani 1 1 d U . .
H32A H 0.7868 0.9799 0.3516 0.103 Uiso 1 1 calc R . .
H32B H 0.8281 1.0674 0.4138 0.103 Uiso 1 1 calc R . .
H32C H 0.7775 1.1168 0.3409 0.103 Uiso 1 1 calc R . .
H12 H 0.4154(8) 0.8167(16) 0.2877(16) 0.018(5) Uiso 1 1 d . . .
H13 H 0.4310(9) 0.9425(17) 0.4771(18) 0.027(5) Uiso 1 1 d . . .
H14 H 0.5183(9) 1.0384(19) 0.558(2) 0.033(6) Uiso 1 1 d . . .
H18 H 0.3739(10) 0.740(2) 0.043(2) 0.050(7) Uiso 1 1 d . . .
H19 H 0.3919(11) 0.611(2) 0.043(2) 0.056(8) Uiso 1 1 d . . .
H20 H 0.3744(9) 0.666(2) 0.159(2) 0.049(7) 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
Si1 C29 1.845(2) . ?
Si1 C31 1.850(2) . ?
Si1 C32 1.851(3) . ?
Si1 C30 1.851(2) . ?
F1 B1 1.379(2) . ?
F2 B1 1.385(2) . ?
N1 C1 1.338(3) . ?
N1 C4 1.404(2) . ?
N1 B1 1.568(3) . ?
N2 C9 1.368(2) . ?
N2 C6 1.387(2) . ?
N2 B1 1.548(3) . ?
C1 C2 1.421(3) . ?
C1 C10 1.482(3) . ?
C2 C3 1.359(3) . ?
C2 H1 0.85(2) . ?
C3 C4 1.435(3) . ?
C3 C11 1.491(3) . ?
C4 C5 1.365(3) . ?
C5 C6 1.408(3) . ?
C5 H2 0.989(18) . ?
C6 C7 1.394(3) . ?
C7 C8 1.381(3) . ?
C7 H3 0.93(2) . ?
C8 C9 1.399(3) . ?
C8 H4 0.95(2) . ?
C9 C12 1.425(3) . ?
C10 H5 0.9800 . ?
C10 H6 0.9800 . ?
C10 H7 0.9800 . ?
C11 H8 0.92(4) . ?
C11 H9 0.99(4) . ?
C11 H10 0.94(3) . ?
C12 C13 1.198(3) . ?
C13 Si2 1.843(2) . ?
C14 Si2 1.848(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 Si2 1.854(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 Si2 1.855(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N3 C17 1.335(3) . ?
N3 C20 1.407(2) . ?
N3 B2 1.559(3) . ?
N4 C25 1.370(2) . ?
N4 C22 1.386(2) . ?
N4 B2 1.551(3) . ?
B2 F4 1.380(2) . ?
B2 F3 1.386(3) . ?
C17 C18 1.418(3) . ?
C17 C27 1.483(3) . ?
C18 C19 1.364(3) . ?
C18 H11 0.96(2) . ?
C19 C20 1.434(3) . ?
C19 C26 1.495(2) . ?
C20 C21 1.357(3) . ?
C21 C22 1.413(3) . ?
C21 H12 0.946(18) . ?
C22 C23 1.398(3) . ?
C23 C24 1.384(3) . ?
C23 H13 0.98(2) . ?
C24 C25 1.398(3) . ?
C24 H14 0.98(2) . ?
C25 C28 1.422(2) . ?
C26 H18 0.99(3) . ?
C26 H19 0.92(3) . ?
C26 H20 1.07(3) . ?
C27 H15 0.9800 . ?
C27 H16 0.9800 . ?
C27 H17 0.9800 . ?
C28 C29 1.212(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
C29 Si1 C31 109.94(10) . . ?
C29 Si1 C32 108.90(11) . . ?
C31 Si1 C32 109.29(13) . . ?
C29 Si1 C30 106.72(10) . . ?
C31 Si1 C30 110.52(12) . . ?
C32 Si1 C30 111.43(13) . . ?
C1 N1 C4 107.61(16) . . ?
C1 N1 B1 127.00(15) . . ?
C4 N1 B1 125.39(16) . . ?
C9 N2 C6 106.66(15) . . ?
C9 N2 B1 127.28(15) . . ?
C6 N2 B1 126.06(15) . . ?
F1 B1 F2 110.77(15) . . ?
F1 B1 N2 110.63(16) . . ?
F2 B1 N2 110.12(16) . . ?
F1 B1 N1 109.69(16) . . ?
F2 B1 N1 109.44(16) . . ?
N2 B1 N1 106.08(14) . . ?
N1 C1 C2 109.61(18) . . ?
N1 C1 C10 123.50(19) . . ?
C2 C1 C10 126.9(2) . . ?
C3 C2 C1 108.3(2) . . ?
C3 C2 H1 130.3(14) . . ?
C1 C2 H1 121.1(15) . . ?
C2 C3 C4 106.55(17) . . ?
C2 C3 C11 128.8(2) . . ?
C4 C3 C11 124.7(2) . . ?
C5 C4 N1 120.19(17) . . ?
C5 C4 C3 131.84(17) . . ?
N1 C4 C3 107.97(16) . . ?
C4 C5 C6 122.38(16) . . ?
C4 C5 H2 119.0(12) . . ?
C6 C5 H2 118.6(12) . . ?
N2 C6 C7 109.28(17) . . ?
N2 C6 C5 119.88(17) . . ?
C7 C6 C5 130.84(17) . . ?
C8 C7 C6 107.18(17) . . ?
C8 C7 H3 128.4(15) . . ?
C6 C7 H3 124.3(15) . . ?
C7 C8 C9 107.34(18) . . ?
C7 C8 H4 132.0(12) . . ?
C9 C8 H4 120.2(12) . . ?
N2 C9 C8 109.54(17) . . ?
N2 C9 C12 122.64(17) . . ?
C8 C9 C12 127.81(18) . . ?
C1 C10 H5 109.5 . . ?
C1 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
C1 C10 H7 109.5 . . ?
H5 C10 H7 109.5 . . ?
H6 C10 H7 109.5 . . ?
C3 C11 H8 109(2) . . ?
C3 C11 H9 110.3(19) . . ?
H8 C11 H9 97(3) . . ?
C3 C11 H10 119.3(18) . . ?
H8 C11 H10 119(3) . . ?
H9 C11 H10 98(3) . . ?
C13 C12 C9 176.8(2) . . ?
C12 C13 Si2 178.6(2) . . ?
Si2 C14 H14A 109.5 . . ?
Si2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si2 C15 H15A 109.5 . . ?
Si2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si2 C16 H16A 109.5 . . ?
Si2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 Si2 C14 107.49(10) . . ?
C13 Si2 C16 108.85(12) . . ?
C14 Si2 C16 111.70(13) . . ?
C13 Si2 C15 107.28(13) . . ?
C14 Si2 C15 111.67(14) . . ?
C16 Si2 C15 109.69(15) . . ?
C17 N3 C20 107.90(15) . . ?
C17 N3 B2 127.29(15) . . ?
C20 N3 B2 124.80(16) . . ?
C25 N4 C22 107.08(15) . . ?
C25 N4 B2 127.46(14) . . ?
C22 N4 B2 125.46(14) . . ?
F4 B2 F3 110.46(15) . . ?
F4 B2 N4 110.31(16) . . ?
F3 B2 N4 110.34(16) . . ?
F4 B2 N3 109.82(16) . . ?
F3 B2 N3 109.10(16) . . ?
N4 B2 N3 106.72(13) . . ?
N3 C17 C18 109.69(17) . . ?
N3 C17 C27 123.15(18) . . ?
C18 C17 C27 127.2(2) . . ?
C19 C18 C17 108.11(19) . . ?
C19 C18 H11 124.8(13) . . ?
C17 C18 H11 127.1(13) . . ?
C18 C19 C20 106.70(16) . . ?
C18 C19 C26 127.79(19) . . ?
C20 C19 C26 125.50(19) . . ?
C21 C20 N3 120.87(16) . . ?
C21 C20 C19 131.55(16) . . ?
N3 C20 C19 107.58(16) . . ?
C20 C21 C22 121.98(15) . . ?
C20 C21 H12 122.6(12) . . ?
C22 C21 H12 115.4(12) . . ?
N4 C22 C23 108.79(16) . . ?
N4 C22 C21 120.14(16) . . ?
C23 C22 C21 131.03(17) . . ?
C24 C23 C22 107.46(17) . . ?
C24 C23 H13 125.9(13) . . ?
C22 C23 H13 126.6(13) . . ?
C23 C24 C25 107.19(18) . . ?
C23 C24 H14 126.5(13) . . ?
C25 C24 H14 126.2(13) . . ?
N4 C25 C24 109.47(16) . . ?
N4 C25 C28 123.93(17) . . ?
C24 C25 C28 126.56(18) . . ?
C19 C26 H18 109.9(14) . . ?
C19 C26 H19 111.1(16) . . ?
H18 C26 H19 107(2) . . ?
C19 C26 H20 113.1(13) . . ?
H18 C26 H20 107.3(19) . . ?
H19 C26 H20 108(2) . . ?
C17 C27 H15 109.5 . . ?
C17 C27 H16 109.5 . . ?
H15 C27 H16 109.5 . . ?
C17 C27 H17 109.5 . . ?
H15 C27 H17 109.5 . . ?
H16 C27 H17 109.5 . . ?
C29 C28 C25 175.0(2) . . ?
C28 C29 Si1 173.08(19) . . ?
Si1 C30 H30A 109.5 . . ?
Si1 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
Si1 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
Si1 C31 H31A 109.5 . . ?
Si1 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
Si1 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
Si1 C32 H32A 109.5 . . ?
Si1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
Si1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.90
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_database_code_depnum_ccdc_archive 'CCDC 1010899'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sh3481

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 B F2 N2 Si'
_chemical_formula_sum            'C16 H19 B F2 N2 Si'
_chemical_formula_weight         316.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0599(4)
_cell_length_b                   9.2121(7)
_cell_length_c                   13.9179(7)
_cell_angle_alpha                88.475(3)
_cell_angle_beta                 76.337(4)
_cell_angle_gamma                72.777(4)
_cell_volume                     839.20(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    3551
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.74

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9344
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   'SADABS, BrukerAXS 2010'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19906
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         27.10
_reflns_number_total             3689
_reflns_number_gt                2631
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0733P)²+0.2049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3689
_refine_ls_number_parameters     253
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.026
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si Si 0.81609(10) 0.75514(7) 0.57436(4) 0.02808(19) Uani 1 1 d U . .
F1 F 1.00369(19) 0.19549(13) 1.08125(9) 0.0292(3) Uani 1 1 d U . .
F2 F 0.68499(19) 0.18918(14) 1.08445(9) 0.0303(3) Uani 1 1 d U . .
N1 N 0.7356(3) 0.43463(19) 1.09943(13) 0.0220(4) Uani 1 1 d U . .
N2 N 0.8669(3) 0.28430(18) 0.93950(13) 0.0218(4) Uani 1 1 d U . .
B1 B 0.8241(4) 0.2698(3) 1.05273(18) 0.0235(5) Uani 1 1 d U . .
C1 C 0.9464(3) 0.1688(2) 0.86930(16) 0.0251(5) Uani 1 1 d U . .
C2 C 0.9599(3) 0.2259(2) 0.77591(17) 0.0271(5) Uani 1 1 d U . .
C3 C 0.8844(3) 0.3852(2) 0.78882(15) 0.0220(4) Uani 1 1 d U . .
C4 C 0.8275(3) 0.4190(2) 0.89157(15) 0.0215(4) Uani 1 1 d U . .
C5 C 0.7446(3) 0.5595(2) 0.94487(16) 0.0213(4) Uani 1 1 d U . .
C6 C 0.7003(3) 0.5679(2) 1.04586(15) 0.0216(4) Uani 1 1 d U . .
C7 C 0.6180(3) 0.6963(2) 1.11496(16) 0.0229(4) Uani 1 1 d U . .
C8 C 0.6063(3) 0.6379(3) 1.20725(17) 0.0269(5) Uani 1 1 d U . .
C9 C 0.6784(3) 0.4781(2) 1.19629(15) 0.0248(5) Uani 1 1 d U . .
C10 C 0.8654(3) 0.4967(2) 0.71624(16) 0.0245(5) Uani 1 1 d U . .
C11 C 0.8482(3) 0.5951(2) 0.65677(16) 0.0276(5) Uani 1 1 d U . .
C12 C 1.0713(4) 0.7697(3) 0.5085(2) 0.0354(6) Uani 1 1 d U . .
C13 C 0.6765(4) 0.7231(4) 0.4837(2) 0.0432(7) Uani 1 1 d U . .
C14 C 0.6709(5) 0.9304(3) 0.6544(3) 0.0513(8) Uani 1 1 d U . .
C15 C 0.5603(3) 0.8584(2) 1.08803(17) 0.0287(5) Uani 1 1 d U . .
H15A H 0.4147 0.8930 1.0886 0.043 Uiso 1 1 calc R . .
H15B H 0.6410 0.8678 1.0217 0.043 Uiso 1 1 calc R . .
H15C H 0.5873 0.9209 1.1360 0.043 Uiso 1 1 calc R . .
C16 C 0.6961(4) 0.3661(3) 1.27497(17) 0.0335(5) Uani 1 1 d U . .
H16A H 0.6161 0.2974 1.2696 0.050 Uiso 1 1 calc R . .
H16B H 0.6441 0.4201 1.3400 0.050 Uiso 1 1 calc R . .
H16C H 0.8397 0.3071 1.2672 0.050 Uiso 1 1 calc R . .
H1 H 0.976(4) 0.067(3) 0.8877(18) 0.037(7) Uiso 1 1 d . . .
H2 H 1.012(4) 0.169(3) 0.714(2) 0.047(8) Uiso 1 1 d . . .
H3 H 0.724(3) 0.650(3) 0.9101(17) 0.029(6) Uiso 1 1 d . . .
H4 H 0.550(4) 0.700(3) 1.2728(18) 0.029(6) Uiso 1 1 d . . .
H5 H 1.149(4) 0.784(3) 0.5573(19) 0.034(6) Uiso 1 1 d . . .
H6 H 1.051(4) 0.848(3) 0.459(2) 0.058(9) Uiso 1 1 d . . .
H7 H 1.150(4) 0.678(4) 0.475(2) 0.049(8) Uiso 1 1 d . . .
H8 H 0.662(5) 0.805(4) 0.438(3) 0.074(10) Uiso 1 1 d . . .
H9 H 0.531(5) 0.724(4) 0.518(2) 0.074(10) Uiso 1 1 d . . .
H10 H 0.753(5) 0.625(4) 0.443(2) 0.063(9) Uiso 1 1 d . . .
H11 H 0.745(6) 0.945(4) 0.703(3) 0.091(13) Uiso 1 1 d . . .
H12 H 0.656(5) 1.016(4) 0.615(2) 0.071(10) Uiso 1 1 d . . .
H13 H 0.529(5) 0.924(4) 0.691(2) 0.069(10) 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
Si C11 1.837(2) . ?
Si C13 1.852(3) . ?
Si C12 1.861(3) . ?
Si C14 1.864(3) . ?
F1 B1 1.394(3) . ?
F2 B1 1.386(3) . ?
N1 C9 1.348(3) . ?
N1 C6 1.408(3) . ?
N1 B1 1.554(3) . ?
N2 C1 1.358(3) . ?
N2 C4 1.379(2) . ?
N2 B1 1.543(3) . ?
C1 C2 1.382(3) . ?
C1 H1 0.94(3) . ?
C2 C3 1.405(3) . ?
C2 H2 0.95(3) . ?
C3 C4 1.408(3) . ?
C3 C10 1.422(3) . ?
C4 C5 1.402(3) . ?
C5 C6 1.365(3) . ?
C5 H3 0.95(2) . ?
C6 C7 1.432(3) . ?
C7 C8 1.373(3) . ?
C7 C15 1.490(3) . ?
C8 C9 1.407(3) . ?
C8 H4 1.02(2) . ?
C9 C16 1.486(3) . ?
C10 C11 1.210(3) . ?
C12 H5 1.00(3) . ?
C12 H6 0.98(3) . ?
C12 H7 0.93(3) . ?
C13 H8 0.97(4) . ?
C13 H9 1.02(3) . ?
C13 H10 1.01(3) . ?
C14 H11 0.98(4) . ?
C14 H12 0.94(4) . ?
C14 H13 1.03(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C11 Si C13 109.22(12) . . ?
C11 Si C12 109.47(11) . . ?
C13 Si C12 109.95(13) . . ?
C11 Si C14 106.82(13) . . ?
C13 Si C14 111.59(16) . . ?
C12 Si C14 109.73(14) . . ?
C9 N1 C6 107.20(17) . . ?
C9 N1 B1 127.71(17) . . ?
C6 N1 B1 125.09(17) . . ?
C1 N2 C4 107.68(17) . . ?
C1 N2 B1 126.87(17) . . ?
C4 N2 B1 125.45(17) . . ?
F2 B1 F1 108.60(17) . . ?
F2 B1 N2 111.03(17) . . ?
F1 B1 N2 110.64(18) . . ?
F2 B1 N1 110.16(18) . . ?
F1 B1 N1 109.88(17) . . ?
N2 B1 N1 106.53(16) . . ?
N2 C1 C2 110.26(19) . . ?
N2 C1 H1 120.4(15) . . ?
C2 C1 H1 129.3(15) . . ?
C1 C2 C3 106.9(2) . . ?
C1 C2 H2 127.0(17) . . ?
C3 C2 H2 126.1(17) . . ?
C2 C3 C4 106.61(18) . . ?
C2 C3 C10 129.3(2) . . ?
C4 C3 C10 124.14(19) . . ?
N2 C4 C5 121.07(18) . . ?
N2 C4 C3 108.54(17) . . ?
C5 C4 C3 130.40(19) . . ?
C6 C5 C4 121.24(19) . . ?
C6 C5 H3 119.4(14) . . ?
C4 C5 H3 119.3(14) . . ?
C5 C6 N1 120.61(18) . . ?
C5 C6 C7 131.04(19) . . ?
N1 C6 C7 108.34(17) . . ?
C8 C7 C6 106.01(19) . . ?
C8 C7 C15 128.8(2) . . ?
C6 C7 C15 125.16(19) . . ?
C7 C8 C9 108.6(2) . . ?
C7 C8 H4 125.4(13) . . ?
C9 C8 H4 125.9(13) . . ?
N1 C9 C8 109.79(19) . . ?
N1 C9 C16 122.0(2) . . ?
C8 C9 C16 128.2(2) . . ?
C11 C10 C3 177.9(2) . . ?
C10 C11 Si 175.65(19) . . ?
Si C12 H5 110.1(14) . . ?
Si C12 H6 108.2(17) . . ?
H5 C12 H6 116(2) . . ?
Si C12 H7 110.0(17) . . ?
H5 C12 H7 104(2) . . ?
H6 C12 H7 108(2) . . ?
Si C13 H8 110.5(19) . . ?
Si C13 H9 110.8(18) . . ?
H8 C13 H9 106(3) . . ?
Si C13 H10 110.9(18) . . ?
H8 C13 H10 107(3) . . ?
H9 C13 H10 111(2) . . ?
Si C14 H11 111(2) . . ?
Si C14 H12 109(2) . . ?
H11 C14 H12 107(3) . . ?
Si C14 H13 110.4(18) . . ?
H11 C14 H13 109(3) . . ?
H12 C14 H13 110(3) . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.059
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_database_code_depnum_ccdc_archive 'CCDC 1010900'
