# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060124'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-08-28 downloaded from the CCDC.
;

_audit_creation_date             2015-04-16T16:06:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'C21 H20 B N O2'
_chemical_formula_moiety         'C21 H20 B N O2'
_chemical_formula_sum            'C21 H20 B N O2'
_chemical_formula_weight         329.19

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7590(3)
_cell_length_b                   10.0001(3)
_cell_length_c                   10.2662(4)
_cell_angle_alpha                107.921(2)
_cell_angle_beta                 100.656(2)
_cell_angle_gamma                104.952(2)
_cell_volume                     882.11(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1100
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      21.51
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.154
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.9773
_exptl_absorpt_correction_T_max  0.988

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

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_number            15422
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         26.64
_diffrn_reflns_theta_full        26.64
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             3675
_reflns_number_gt                1976
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker Instrument Service v2011.2.0.0'
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.023(4)
_refine_ls_number_reflns         3675
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.04

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
O2 O 0.72926(15) 0.73286(15) 0.28374(15) 0.0473(4) Uani 1 1 d . . .
O1 O 0.72830(15) 0.48047(15) 0.21356(15) 0.0480(4) Uani 1 1 d . . .
C12 C 0.7268(4) 0.7180(3) -0.3899(3) 0.0814(9) Uani 1 1 d . . .
H12 H 0.7002 0.705 -0.4859 0.098 Uiso 1 1 calc R . .
C5 C 0.7191(2) 0.1049(3) -0.1070(3) 0.0564(7) Uani 1 1 d . . .
H5 H 0.7149 0.0194 -0.1795 0.068 Uiso 1 1 calc R . .
C4 C 0.6791(2) 0.0962(3) 0.0138(3) 0.0582(7) Uani 1 1 d . . .
H4 H 0.6486 0.0037 0.022 0.07 Uiso 1 1 calc R . .
C3 C 0.6835(2) 0.2206(2) 0.1213(3) 0.0514(6) Uani 1 1 d . . .
H3 H 0.6553 0.2118 0.2009 0.062 Uiso 1 1 calc R . .
C2 C 0.7300(2) 0.3601(2) 0.1116(2) 0.0403(5) Uani 1 1 d . . .
B1 B 0.8091(3) 0.6363(3) 0.2328(3) 0.0409(6) Uani 1 1 d . . .
C16 C 0.9754(2) 0.6990(2) 0.3344(2) 0.0408(5) Uani 1 1 d . . .
C21 C 1.0484(3) 0.6054(3) 0.3664(2) 0.0545(6) Uani 1 1 d . . .
H21 H 0.9981 0.5031 0.33 0.065 Uiso 1 1 calc R . .
C20 C 1.1936(3) 0.6601(3) 0.4508(3) 0.0689(7) Uani 1 1 d . . .
H20 H 1.2396 0.5946 0.4694 0.083 Uiso 1 1 calc R . .
C19 C 1.2699(3) 0.8106(3) 0.5072(3) 0.0677(7) Uani 1 1 d . . .
H19 H 1.3679 0.8473 0.5631 0.081 Uiso 1 1 calc R . .
C11 C 0.8729(4) 0.7722(3) -0.3139(3) 0.0777(9) Uani 1 1 d . . .
H11 H 0.9456 0.7961 -0.3581 0.093 Uiso 1 1 calc R . .
C10 C 0.9126(3) 0.7914(3) -0.1718(3) 0.0588(7) Uani 1 1 d . . .
H10 H 1.0122 0.8282 -0.1205 0.071 Uiso 1 1 calc R . .
C9 C 0.8058(2) 0.7566(2) -0.1045(2) 0.0421(5) Uani 1 1 d . . .
C8 C 0.8488(3) 0.7743(2) 0.0494(2) 0.0478(6) Uani 1 1 d . . .
H8B H 0.954 0.8295 0.0907 0.057 Uiso 1 1 calc R . .
H8A H 0.7966 0.8331 0.1001 0.057 Uiso 1 1 calc R . .
N1 N 0.81685(17) 0.63143(18) 0.07255(17) 0.0391(4) Uani 1 1 d . . .
C15 C 0.5774(2) 0.6926(3) 0.2122(3) 0.0634(7) Uani 1 1 d . . .
H15A H 0.5626 0.655 0.1108 0.095 Uiso 1 1 calc R . .
H15B H 0.547 0.7786 0.2392 0.095 Uiso 1 1 calc R . .
H15C H 0.5198 0.6168 0.2382 0.095 Uiso 1 1 calc R . .
C6 C 0.7650(2) 0.2417(2) -0.1178(2) 0.0490(6) Uani 1 1 d . . .
H6 H 0.7921 0.249 -0.1983 0.059 Uiso 1 1 calc R . .
C1 C 0.7715(2) 0.3699(2) -0.0093(2) 0.0393(5) Uani 1 1 d . . .
C7 C 0.8069(2) 0.5105(2) -0.0263(2) 0.0403(5) Uani 1 1 d . . .
C18 C 1.2003(3) 0.9069(3) 0.4805(3) 0.0598(7) Uani 1 1 d . . .
H18 H 1.2506 1.0093 0.5197 0.072 Uiso 1 1 calc R . .
C17 C 1.0553(2) 0.8511(3) 0.3951(2) 0.0487(6) Uani 1 1 d . . .
H17 H 1.0098 0.9174 0.3777 0.058 Uiso 1 1 calc R . .
C14 C 0.6584(3) 0.7023(3) -0.1834(3) 0.0522(6) Uani 1 1 d . . .
H14 H 0.5851 0.6789 -0.1397 0.063 Uiso 1 1 calc R . .
C13 C 0.6192(3) 0.6825(3) -0.3251(3) 0.0687(8) Uani 1 1 d . . .
H13 H 0.5198 0.6452 -0.3772 0.082 Uiso 1 1 calc R . .
H7 H 0.8205(18) 0.512(2) -0.114(2) 0.033(5) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C15 1.416(2) . ?
O2 B1 1.429(3) . ?
O1 C2 1.337(2) . ?
O1 B1 1.486(3) . ?
C12 C11 1.366(4) . ?
C12 C13 1.372(4) . ?
C12 H12 0.93 . ?
C5 C6 1.371(3) . ?
C5 C4 1.389(3) . ?
C5 H5 0.93 . ?
C4 C3 1.370(3) . ?
C4 H4 0.93 . ?
C3 C2 1.392(3) . ?
C3 H3 0.93 . ?
C2 C1 1.398(3) . ?
B1 C16 1.600(3) . ?
B1 N1 1.647(3) . ?
C16 C17 1.390(3) . ?
C16 C21 1.392(3) . ?
C21 C20 1.382(3) . ?
C21 H21 0.93 . ?
C20 C19 1.371(3) . ?
C20 H20 0.93 . ?
C19 C18 1.377(3) . ?
C19 H19 0.93 . ?
C11 C10 1.377(4) . ?
C11 H11 0.93 . ?
C10 C9 1.382(3) . ?
C10 H10 0.93 . ?
C9 C14 1.383(3) . ?
C9 C8 1.500(3) . ?
C8 N1 1.483(3) . ?
C8 H8B 0.97 . ?
C8 H8A 0.97 . ?
N1 C7 1.284(2) . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C6 C1 1.394(3) . ?
C6 H6 0.93 . ?
C1 C7 1.432(3) . ?
C7 H7 0.937(18) . ?
C18 C17 1.383(3) . ?
C18 H18 0.93 . ?
C17 H17 0.93 . ?
C14 C13 1.372(3) . ?
C14 H14 0.93 . ?
C13 H13 0.93 . ?

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 O2 B1 119.32(18) . . ?
C2 O1 B1 123.79(16) . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120 . . ?
C2 C3 H3 120 . . ?
O1 C2 C3 120.1(2) . . ?
O1 C2 C1 121.15(19) . . ?
C3 C2 C1 118.7(2) . . ?
O2 B1 O1 110.77(17) . . ?
O2 B1 C16 110.75(18) . . ?
O1 B1 C16 113.09(18) . . ?
O2 B1 N1 108.40(17) . . ?
O1 B1 N1 105.80(16) . . ?
C16 B1 N1 107.76(16) . . ?
C17 C16 C21 116.3(2) . . ?
C17 C16 B1 121.41(19) . . ?
C21 C16 B1 122.3(2) . . ?
C20 C21 C16 121.9(2) . . ?
C20 C21 H21 119 . . ?
C16 C21 H21 119 . . ?
C19 C20 C21 120.3(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C19 C18 119.5(2) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C9 C14 118.4(2) . . ?
C10 C9 C8 120.8(2) . . ?
C14 C9 C8 120.83(19) . . ?
N1 C8 C9 114.29(17) . . ?
N1 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
N1 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
H8B C8 H8A 107.6 . . ?
C7 N1 C8 120.68(18) . . ?
C7 N1 B1 121.37(18) . . ?
C8 N1 B1 117.75(16) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C6 C1 C2 120.2(2) . . ?
C6 C1 C7 120.4(2) . . ?
C2 C1 C7 119.10(19) . . ?
N1 C7 C1 122.1(2) . . ?
N1 C7 H7 120.3(11) . . ?
C1 C7 H7 117.6(11) . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C17 C16 122.2(2) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120 . . ?
C12 C13 H13 120 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C5 C4 C3 0.5(3) . . . . ?
C5 C4 C3 C2 -0.6(3) . . . . ?
B1 O1 C2 C3 164.08(19) . . . . ?
B1 O1 C2 C1 -19.0(3) . . . . ?
C4 C3 C2 O1 177.14(18) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C15 O2 B1 O1 -50.5(2) . . . . ?
C15 O2 B1 C16 -176.80(17) . . . . ?
C15 O2 B1 N1 65.2(2) . . . . ?
C2 O1 B1 O2 146.70(18) . . . . ?
C2 O1 B1 C16 -88.3(2) . . . . ?
C2 O1 B1 N1 29.4(2) . . . . ?
O2 B1 C16 C17 -38.0(3) . . . . ?
O1 B1 C16 C17 -163.06(17) . . . . ?
N1 B1 C16 C17 80.4(2) . . . . ?
O2 B1 C16 C21 142.3(2) . . . . ?
O1 B1 C16 C21 17.3(3) . . . . ?
N1 B1 C16 C21 -99.3(2) . . . . ?
C17 C16 C21 C20 -1.6(3) . . . . ?
B1 C16 C21 C20 178.0(2) . . . . ?
C16 C21 C20 C19 0.7(4) . . . . ?
C21 C20 C19 C18 0.7(4) . . . . ?
C13 C12 C11 C10 0.0(4) . . . . ?
C12 C11 C10 C9 -0.1(4) . . . . ?
C11 C10 C9 C14 -0.1(3) . . . . ?
C11 C10 C9 C8 178.6(2) . . . . ?
C10 C9 C8 N1 -110.3(2) . . . . ?
C14 C9 C8 N1 68.4(3) . . . . ?
C9 C8 N1 C7 24.2(3) . . . . ?
C9 C8 N1 B1 -160.91(17) . . . . ?
O2 B1 N1 C7 -142.56(18) . . . . ?
O1 B1 N1 C7 -23.7(2) . . . . ?
C16 B1 N1 C7 97.5(2) . . . . ?
O2 B1 N1 C8 42.6(2) . . . . ?
O1 B1 N1 C8 161.47(16) . . . . ?
C16 B1 N1 C8 -77.3(2) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C5 C6 C1 C2 -0.5(3) . . . . ?
C5 C6 C1 C7 -174.47(19) . . . . ?
O1 C2 C1 C6 -176.60(18) . . . . ?
C3 C2 C1 C6 0.4(3) . . . . ?
O1 C2 C1 C7 -2.5(3) . . . . ?
C3 C2 C1 C7 174.47(18) . . . . ?
C8 N1 C7 C1 -177.96(17) . . . . ?
B1 N1 C7 C1 7.4(3) . . . . ?
C6 C1 C7 N1 -178.51(18) . . . . ?
C2 C1 C7 N1 7.4(3) . . . . ?
C20 C19 C18 C17 -1.2(4) . . . . ?
C19 C18 C17 C16 0.2(3) . . . . ?
C21 C16 C17 C18 1.2(3) . . . . ?
B1 C16 C17 C18 -178.5(2) . . . . ?
C10 C9 C14 C13 0.4(3) . . . . ?
C8 C9 C14 C13 -178.3(2) . . . . ?
C9 C14 C13 C12 -0.5(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?


# END of CIF
