# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_17399
_database_code_depnum_ccdc_archive 'CCDC 1443748'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-1H-tetrazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 B Cl N4 O2'
_chemical_formula_sum            'C14 H18 B Cl N4 O2'
_chemical_formula_weight         320.58

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   15.8491(11)
_cell_length_b                   10.2222(8)
_cell_length_c                   10.1374(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.018(3)
_cell_angle_gamma                90.00
_cell_volume                     1612.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8860
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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 APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7566
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2851
_reflns_number_gt                2052
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1136P)²+1.0272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2851
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.2057
_refine_ls_wR_factor_gt          0.1745
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1603(2) 0.4078(4) 0.5630(4) 0.0498(10) Uani 1 1 d . . .
C2 C 0.1131(4) 0.2845(6) 0.5860(5) 0.0935(18) Uani 1 1 d . . .
H2A H 0.0512 0.3023 0.5717 0.140 Uiso 1 1 calc R . .
H2B H 0.1331 0.2541 0.6784 0.140 Uiso 1 1 calc R . .
H2C H 0.1241 0.2168 0.5230 0.140 Uiso 1 1 calc R . .
C3 C 0.1318(4) 0.5171(5) 0.6489(5) 0.0820(15) Uani 1 1 d . . .
H3A H 0.0689 0.5206 0.6330 0.123 Uiso 1 1 calc R . .
H3B H 0.1542 0.6011 0.6244 0.123 Uiso 1 1 calc R . .
H3C H 0.1541 0.4992 0.7442 0.123 Uiso 1 1 calc R . .
C4 C 0.2586(3) 0.3969(4) 0.5822(4) 0.0497(10) Uani 1 1 d . . .
C5 C 0.2893(5) 0.2620(6) 0.5512(8) 0.130(3) Uani 1 1 d . . .
H5A H 0.2561 0.2317 0.4650 0.195 Uiso 1 1 calc R . .
H5B H 0.2812 0.2011 0.6225 0.195 Uiso 1 1 calc R . .
H5C H 0.3503 0.2658 0.5461 0.195 Uiso 1 1 calc R . .
C6 C 0.3088(4) 0.4458(8) 0.7124(5) 0.109(2) Uani 1 1 d . . .
H6A H 0.2878 0.5327 0.7313 0.164 Uiso 1 1 calc R . .
H6B H 0.3697 0.4515 0.7069 0.164 Uiso 1 1 calc R . .
H6C H 0.3018 0.3855 0.7847 0.164 Uiso 1 1 calc R . .
C7 C 0.2090(2) 0.5576(3) 0.2433(3) 0.0299(7) Uani 1 1 d . . .
C8 C 0.1394(2) 0.5977(4) 0.1464(3) 0.0400(8) Uani 1 1 d . . .
C9 C 0.1491(2) 0.6478(4) 0.0236(3) 0.0448(9) Uani 1 1 d . . .
H9 H 0.1000 0.6735 -0.0405 0.054 Uiso 1 1 calc R . .
C10 C 0.2295(2) 0.6603(3) -0.0054(3) 0.0375(8) Uani 1 1 d . . .
H10 H 0.2361 0.6954 -0.0896 0.045 Uiso 1 1 calc R . .
C11 C 0.3018(2) 0.6221(3) 0.0875(3) 0.0285(7) Uani 1 1 d . . .
C12 C 0.2903(2) 0.5711(3) 0.2092(3) 0.0280(7) Uani 1 1 d . . .
H12 H 0.3395 0.5440 0.2724 0.034 Uiso 1 1 calc R . .
C13 C 0.3909(2) 0.6318(3) 0.0555(3) 0.0348(8) Uani 1 1 d . . .
H13A H 0.4237 0.5519 0.0879 0.042 Uiso 1 1 calc R . .
H13B H 0.3862 0.6362 -0.0432 0.042 Uiso 1 1 calc R . .
C14 C 0.4705(2) 0.8480(3) 0.0621(3) 0.0345(8) Uani 1 1 d . . .
H14 H 0.4660 0.8618 -0.0317 0.041 Uiso 1 1 calc R . .
B1 B 0.2051(2) 0.4944(4) 0.3818(4) 0.0333(8) Uani 1 1 d . . .
N1 N 0.43801(16) 0.7469(2) 0.1172(2) 0.0285(6) Uani 1 1 d . . .
N2 N 0.4563(2) 0.7626(3) 0.2512(3) 0.0404(7) Uani 1 1 d . . .
N3 N 0.49992(19) 0.8698(3) 0.2738(3) 0.0404(7) Uani 1 1 d . . .
N4 N 0.50993(19) 0.9263(3) 0.1570(3) 0.0396(7) Uani 1 1 d . . .
O1 O 0.13574(17) 0.4468(3) 0.4237(3) 0.0679(9) Uani 1 1 d . . .
O2 O 0.27809(16) 0.4836(3) 0.4775(2) 0.0562(8) Uani 1 1 d . . .
Cl1 Cl 0.03569(7) 0.58663(15) 0.17790(12) 0.0805(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.046(2) 0.072(3) 0.0319(18) 0.0132(18) 0.0088(15) -0.0198(19)
C2 0.097(4) 0.108(4) 0.078(4) 0.008(3) 0.022(3) -0.057(3)
C3 0.097(4) 0.087(4) 0.074(3) 0.004(3) 0.045(3) 0.010(3)
C4 0.050(2) 0.067(3) 0.0360(19) 0.0236(18) 0.0158(16) 0.0012(19)
C5 0.161(7) 0.094(5) 0.149(7) 0.052(4) 0.068(5) 0.074(5)
C6 0.074(4) 0.191(7) 0.057(3) 0.022(4) -0.003(3) -0.062(4)
C7 0.0345(17) 0.0294(16) 0.0265(15) -0.0008(13) 0.0074(13) -0.0019(13)
C8 0.0315(18) 0.055(2) 0.0347(18) 0.0043(16) 0.0077(14) 0.0037(15)
C9 0.041(2) 0.057(2) 0.0355(19) 0.0116(17) 0.0064(15) 0.0123(17)
C10 0.055(2) 0.0357(18) 0.0228(15) 0.0051(14) 0.0104(14) 0.0012(16)
C11 0.0411(18) 0.0234(15) 0.0213(14) -0.0023(12) 0.0065(12) -0.0044(13)
C12 0.0362(17) 0.0264(15) 0.0217(15) 0.0010(12) 0.0059(12) -0.0037(13)
C13 0.047(2) 0.0345(17) 0.0262(15) -0.0040(14) 0.0161(14) -0.0072(15)
C14 0.0409(18) 0.0386(18) 0.0254(15) 0.0019(14) 0.0099(14) -0.0098(15)
B1 0.036(2) 0.037(2) 0.0275(18) -0.0018(16) 0.0068(15) -0.0037(16)
N1 0.0364(14) 0.0314(14) 0.0192(12) 0.0022(11) 0.0094(10) -0.0056(11)
N2 0.0586(19) 0.0417(16) 0.0211(14) 0.0015(12) 0.0083(12) -0.0083(14)
N3 0.0472(17) 0.0453(17) 0.0280(15) -0.0013(13) 0.0053(12) -0.0073(14)
N4 0.0459(17) 0.0425(16) 0.0324(15) -0.0011(13) 0.0127(13) -0.0121(13)
O1 0.0439(16) 0.120(3) 0.0393(15) 0.0301(16) 0.0066(12) -0.0196(16)
O2 0.0403(15) 0.090(2) 0.0394(14) 0.0256(14) 0.0096(11) -0.0059(14)
Cl1 0.0350(6) 0.1487(13) 0.0602(7) 0.0365(7) 0.0152(5) 0.0184(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.447(4) . ?
C1 C2 1.507(6) . ?
C1 C3 1.536(6) . ?
C1 C4 1.538(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O2 1.460(4) . ?
C4 C6 1.492(6) . ?
C4 C5 1.514(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.391(5) . ?
C7 C12 1.404(4) . ?
C7 B1 1.557(5) . ?
C8 C9 1.382(5) . ?
C8 Cl1 1.737(3) . ?
C9 C10 1.368(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(4) . ?
C11 C13 1.510(5) . ?
C12 H12 0.9500 . ?
C13 N1 1.467(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N4 1.315(4) . ?
C14 N1 1.325(4) . ?
C14 H14 0.9500 . ?
B1 O1 1.344(5) . ?
B1 O2 1.365(4) . ?
N1 N2 1.344(3) . ?
N2 N3 1.292(4) . ?
N3 N4 1.353(4) . ?

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
O1 C1 C2 109.4(3) . . ?
O1 C1 C3 107.4(4) . . ?
C2 C1 C3 108.2(4) . . ?
O1 C1 C4 102.7(3) . . ?
C2 C1 C4 116.2(4) . . ?
C3 C1 C4 112.5(4) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C6 106.8(4) . . ?
O2 C4 C5 106.4(4) . . ?
C6 C4 C5 110.6(5) . . ?
O2 C4 C1 102.4(3) . . ?
C6 C4 C1 116.3(4) . . ?
C5 C4 C1 113.4(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 116.0(3) . . ?
C8 C7 B1 126.6(3) . . ?
C12 C7 B1 117.3(3) . . ?
C9 C8 C7 122.5(3) . . ?
C9 C8 Cl1 117.4(3) . . ?
C7 C8 Cl1 120.1(3) . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 118.5(3) . . ?
C12 C11 C13 120.3(3) . . ?
C10 C11 C13 121.2(3) . . ?
C11 C12 C7 122.7(3) . . ?
C11 C12 H12 118.6 . . ?
C7 C12 H12 118.6 . . ?
N1 C13 C11 112.4(2) . . ?
N1 C13 H13A 109.1 . . ?
C11 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C11 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
N4 C14 N1 109.6(3) . . ?
N4 C14 H14 125.2 . . ?
N1 C14 H14 125.2 . . ?
O1 B1 O2 112.3(3) . . ?
O1 B1 C7 127.7(3) . . ?
O2 B1 C7 120.0(3) . . ?
C14 N1 N2 107.8(2) . . ?
C14 N1 C13 130.8(3) . . ?
N2 N1 C13 121.4(2) . . ?
N3 N2 N1 106.6(2) . . ?
N2 N3 N4 110.8(3) . . ?
C14 N4 N3 105.2(3) . . ?
B1 O1 C1 109.0(3) . . ?
B1 O2 C4 107.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_a17398
_database_code_depnum_ccdc_archive 'CCDC 1443749'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-tetrazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 B N4 O2'
_chemical_formula_sum            'C13 H17 B N4 O2'
_chemical_formula_weight         272.12

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   17.6880(11)
_cell_length_b                   6.9800(8)
_cell_length_c                   11.9076(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.949(5)
_cell_angle_gamma                90.00
_cell_volume                     1390.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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 APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7550
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2442
_reflns_number_gt                1575
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0496P)²+0.2774P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2442
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.86623(11) 0.4438(4) 0.58593(19) 0.0324(6) Uani 1 1 d . . .
C2 C 0.88464(14) 0.6560(4) 0.5855(2) 0.0521(8) Uani 1 1 d . . .
H2A H 0.8384 0.7302 0.5891 0.078 Uiso 1 1 calc R . .
H2B H 0.8962 0.6882 0.5127 0.078 Uiso 1 1 calc R . .
H2C H 0.9312 0.6866 0.6546 0.078 Uiso 1 1 calc R . .
C3 C 0.93733(12) 0.3264(4) 0.5802(2) 0.0445(7) Uani 1 1 d . . .
H3A H 0.9248 0.1897 0.5804 0.067 Uiso 1 1 calc R . .
H3B H 0.9841 0.3560 0.6492 0.067 Uiso 1 1 calc R . .
H3C H 0.9489 0.3579 0.5072 0.067 Uiso 1 1 calc R . .
C4 C 0.83233(11) 0.3818(4) 0.68700(19) 0.0329(6) Uani 1 1 d . . .
C5 C 0.85917(14) 0.5042(5) 0.7975(2) 0.0549(9) Uani 1 1 d . . .
H5A H 0.8503 0.6396 0.7753 0.082 Uiso 1 1 calc R . .
H5B H 0.9162 0.4824 0.8390 0.082 Uiso 1 1 calc R . .
H5C H 0.8284 0.4699 0.8498 0.082 Uiso 1 1 calc R . .
C6 C 0.84452(13) 0.1709(4) 0.7175(2) 0.0457(7) Uani 1 1 d . . .
H6A H 0.8264 0.0949 0.6444 0.069 Uiso 1 1 calc R . .
H6B H 0.8137 0.1352 0.7694 0.069 Uiso 1 1 calc R . .
H6C H 0.9014 0.1462 0.7583 0.069 Uiso 1 1 calc R . .
C7 C 0.64648(11) 0.4004(3) 0.41570(18) 0.0254(5) Uani 1 1 d . . .
C8 C 0.57812(11) 0.3688(3) 0.44767(18) 0.0266(6) Uani 1 1 d . . .
H8 H 0.5839 0.3483 0.5289 0.032 Uiso 1 1 calc R . .
C9 C 0.50220(11) 0.3664(3) 0.36463(18) 0.0249(5) Uani 1 1 d . . .
H9 H 0.4566 0.3433 0.3881 0.030 Uiso 1 1 calc R . .
C10 C 0.49433(11) 0.3985(3) 0.24669(18) 0.0228(5) Uani 1 1 d . . .
C11 C 0.56077(11) 0.4295(3) 0.21071(18) 0.0257(6) Uani 1 1 d . . .
H11 H 0.5547 0.4503 0.1294 0.031 Uiso 1 1 calc R . .
C12 C 0.63557(11) 0.4296(3) 0.29548(18) 0.0280(6) Uani 1 1 d . . .
H12 H 0.6811 0.4501 0.2713 0.034 Uiso 1 1 calc R . .
C13 C 0.34377(11) 0.4286(3) 0.1679(2) 0.0323(6) Uani 1 1 d . . .
H13 H 0.3332 0.4518 0.2400 0.039 Uiso 1 1 calc R . .
B1 B 0.73146(13) 0.4051(4) 0.5100(2) 0.0285(7) Uani 1 1 d . . .
N1 N 0.41652(9) 0.3997(3) 0.15905(14) 0.0247(5) Uani 1 1 d . . .
N2 N 0.40704(10) 0.3731(3) 0.04282(15) 0.0324(5) Uani 1 1 d . . .
N3 N 0.33102(10) 0.3847(3) -0.01370(16) 0.0390(6) Uani 1 1 d . . .
N4 N 0.28939(10) 0.4201(3) 0.06256(17) 0.0390(6) Uani 1 1 d . . .
O1 O 0.79932(7) 0.4067(2) 0.47887(12) 0.0348(5) Uani 1 1 d . . .
O2 O 0.74575(7) 0.4094(2) 0.62962(12) 0.0355(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0245(10) 0.0429(19) 0.0266(13) 0.0010(12) 0.0038(9) -0.0025(11)
C2 0.0406(13) 0.049(2) 0.0577(18) 0.0076(16) 0.0036(13) -0.0076(13)
C3 0.0313(11) 0.066(2) 0.0378(15) 0.0077(14) 0.0128(11) 0.0066(12)
C4 0.0226(10) 0.049(2) 0.0259(12) -0.0024(13) 0.0056(9) 0.0002(11)
C5 0.0395(13) 0.087(3) 0.0344(15) -0.0172(16) 0.0063(12) -0.0031(14)
C6 0.0369(12) 0.056(2) 0.0426(16) 0.0155(15) 0.0111(11) 0.0009(13)
C7 0.0285(11) 0.0217(15) 0.0249(12) 0.0000(11) 0.0072(9) 0.0039(10)
C8 0.0332(11) 0.0253(16) 0.0218(12) 0.0008(11) 0.0097(9) 0.0021(10)
C9 0.0285(11) 0.0223(16) 0.0268(12) 0.0002(11) 0.0132(9) -0.0011(9)
C10 0.0244(10) 0.0170(14) 0.0252(11) -0.0024(11) 0.0057(9) 0.0021(10)
C11 0.0297(11) 0.0256(16) 0.0231(12) 0.0014(10) 0.0105(9) 0.0023(10)
C12 0.0244(10) 0.0309(17) 0.0305(13) 0.0010(11) 0.0112(9) 0.0011(10)
C13 0.0279(11) 0.0349(18) 0.0342(14) -0.0014(12) 0.0105(10) 0.0003(10)
B1 0.0308(13) 0.0273(19) 0.0270(14) -0.0015(13) 0.0090(11) 0.0028(12)
N1 0.0270(9) 0.0245(13) 0.0227(10) -0.0016(9) 0.0080(8) -0.0027(8)
N2 0.0330(10) 0.0391(15) 0.0226(10) -0.0022(10) 0.0055(8) -0.0025(9)
N3 0.0344(11) 0.0426(17) 0.0337(11) -0.0008(11) 0.0022(9) -0.0015(9)
N4 0.0313(10) 0.0436(17) 0.0377(12) -0.0011(11) 0.0053(9) -0.0009(10)
O1 0.0258(7) 0.0519(13) 0.0246(8) 0.0005(8) 0.0054(6) -0.0011(7)
O2 0.0240(7) 0.0551(14) 0.0259(8) -0.0024(8) 0.0060(6) 0.0022(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.454(2) . ?
C1 C2 1.517(3) . ?
C1 C3 1.521(3) . ?
C1 C4 1.570(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O2 1.473(2) . ?
C4 C5 1.510(3) . ?
C4 C6 1.515(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.396(3) . ?
C7 C8 1.398(2) . ?
C7 B1 1.557(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(2) . ?
C10 N1 1.432(2) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N4 1.311(3) . ?
C13 N1 1.340(2) . ?
C13 H13 0.9500 . ?
B1 O2 1.364(3) . ?
B1 O1 1.366(2) . ?
N1 N2 1.352(2) . ?
N2 N3 1.296(2) . ?
N3 N4 1.365(2) . ?

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
O1 C1 C2 106.59(19) . . ?
O1 C1 C3 108.31(18) . . ?
C2 C1 C3 110.14(18) . . ?
O1 C1 C4 102.61(15) . . ?
C2 C1 C4 114.0(2) . . ?
C3 C1 C4 114.4(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C5 108.40(17) . . ?
O2 C4 C6 106.50(18) . . ?
C5 C4 C6 111.2(2) . . ?
O2 C4 C1 101.94(16) . . ?
C5 C4 C1 115.0(2) . . ?
C6 C4 C1 113.03(18) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 117.29(18) . . ?
C12 C7 B1 121.06(18) . . ?
C8 C7 B1 121.64(19) . . ?
C9 C8 C7 122.09(19) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C10 C9 C8 118.50(18) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 121.38(19) . . ?
C9 C10 N1 119.79(17) . . ?
C11 C10 N1 118.83(19) . . ?
C12 C11 C10 118.67(19) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C7 122.06(18) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
N4 C13 N1 110.03(19) . . ?
N4 C13 H13 125.0 . . ?
N1 C13 H13 125.0 . . ?
O2 B1 O1 113.70(19) . . ?
O2 B1 C7 124.17(18) . . ?
O1 B1 C7 122.1(2) . . ?
C13 N1 N2 107.35(16) . . ?
C13 N1 C10 131.57(18) . . ?
N2 N1 C10 121.05(16) . . ?
N3 N2 N1 106.62(16) . . ?
N2 N3 N4 111.03(17) . . ?
C13 N4 N3 104.97(16) . . ?
B1 O1 C1 107.47(16) . . ?
B1 O2 C4 107.08(15) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-Hexane/ Dichloromethane'
####################################################################### 
# 
# 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_a17514
_database_code_depnum_ccdc_archive 'CCDC 1443750'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2-(4-isocyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 B N O2'
_chemical_formula_sum            'C13 H16 B N O2'
_chemical_formula_weight         229.08

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   11.0964(5)
_cell_length_b                   13.2916(6)
_cell_length_c                   10.4278(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.655(2)
_cell_angle_gamma                90.00
_cell_volume                     1336.54(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9480
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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 APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3767
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.07
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1136
_reflns_number_gt                975
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0506P)²+0.5106P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1136
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0000 -0.1099(2) 0.7500 0.1031(12) Uani 1 2 d S . .
C2 C 0.0000 0.08249(14) 0.7500 0.0406(5) Uani 1 2 d S . .
C3 C 0.07612(14) 0.13316(10) 0.88165(15) 0.0430(4) Uani 1 1 d . . .
H3 H 0.1281 0.0973 0.9715 0.052 Uiso 1 1 calc R . .
C4 C 0.07513(13) 0.23693(10) 0.88016(14) 0.0381(3) Uani 1 1 d . . .
H4 H 0.1272 0.2723 0.9705 0.046 Uiso 1 1 calc R . .
C5 C 0.0000 0.29143(13) 0.7500 0.0327(4) Uani 1 2 d S . .
C6 C 0.07570(12) 0.56988(9) 0.81665(13) 0.0334(3) Uani 1 1 d . . .
C7 C 0.18493(14) 0.59224(12) 0.77321(16) 0.0493(4) Uani 1 1 d . . .
H7A H 0.2773 0.5792 0.8574 0.074 Uiso 1 1 calc R . .
H7B H 0.1783 0.6630 0.7439 0.074 Uiso 1 1 calc R . .
H7C H 0.1697 0.5490 0.6904 0.074 Uiso 1 1 calc R . .
C8 C 0.09868(15) 0.63549(10) 0.94577(15) 0.0453(4) Uani 1 1 d . . .
H8A H 0.0389 0.6123 0.9843 0.068 Uiso 1 1 calc R . .
H8B H 0.0760 0.7054 0.9128 0.068 Uiso 1 1 calc R . .
H8C H 0.1960 0.6311 1.0236 0.068 Uiso 1 1 calc R . .
B1 B 0.0000 0.40865(16) 0.7500 0.0327(5) Uani 1 2 d S . .
N1 N 0.0000 -0.02307(14) 0.7500 0.0626(6) Uani 1 2 d S . .
O1 O 0.09527(8) 0.46467(6) 0.86543(9) 0.0367(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.100(2) 0.0351(18) 0.104(2) 0.000 -0.0030(18) 0.000
C2 0.0345(10) 0.0251(11) 0.0570(12) 0.000 0.0187(9) 0.000
C3 0.0407(7) 0.0348(8) 0.0464(8) 0.0059(6) 0.0162(6) 0.0057(6)
C4 0.0370(7) 0.0329(8) 0.0406(7) -0.0029(5) 0.0164(6) 0.0021(5)
C5 0.0296(9) 0.0307(11) 0.0409(10) 0.000 0.0199(8) 0.000
C6 0.0392(7) 0.0257(8) 0.0368(7) 0.0009(5) 0.0199(6) -0.0012(5)
C7 0.0447(8) 0.0513(10) 0.0569(9) -0.0011(7) 0.0290(7) -0.0081(6)
C8 0.0585(9) 0.0330(8) 0.0414(8) -0.0041(6) 0.0225(7) -0.0024(6)
B1 0.0332(10) 0.0314(12) 0.0382(11) 0.000 0.0212(9) 0.000
N1 0.0555(11) 0.0313(12) 0.0739(13) 0.000 0.0112(10) 0.000
O1 0.0385(5) 0.0275(6) 0.0392(5) 0.0009(4) 0.0155(4) 0.0007(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.154(3) . ?
C2 C3 1.3800(17) . ?
C2 C3 1.3800(17) 2_556 ?
C2 N1 1.403(3) . ?
C3 C4 1.3794(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3937(16) . ?
C4 H4 0.9500 . ?
C5 C4 1.3937(16) 2_556 ?
C5 B1 1.558(3) . ?
C6 O1 1.4669(15) . ?
C6 C8 1.5161(17) . ?
C6 C7 1.5186(17) . ?
C6 C6 1.563(2) 2_556 ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
B1 O1 1.3644(14) . ?
B1 O1 1.3644(14) 2_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C3 121.57(18) . 2_556 ?
C3 C2 N1 119.21(9) . . ?
C3 C2 N1 119.21(9) 2_556 . ?
C4 C3 C2 118.64(13) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 121.89(12) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C4 117.37(17) 2_556 . ?
C4 C5 B1 121.32(8) 2_556 . ?
C4 C5 B1 121.32(8) . . ?
O1 C6 C8 108.02(9) . . ?
O1 C6 C7 106.68(10) . . ?
C8 C6 C7 110.12(11) . . ?
O1 C6 C6 102.59(6) . 2_556 ?
C8 C6 C6 115.11(11) . 2_556 ?
C7 C6 C6 113.57(12) . 2_556 ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 B1 O1 113.85(17) . 2_556 ?
O1 B1 C5 123.07(8) . . ?
O1 B1 C5 123.07(8) 2_556 . ?
C1 N1 C2 180.000(1) . . ?
B1 O1 C6 107.29(10) . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.029
