# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_mo_20150614a_0m
_database_code_depnum_ccdc_archive 'CCDC 1424741'
_audit_update_record             
;
2015-09-16 deposited with the CCDC.
2015-11-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 B N3 O'
_chemical_formula_weight         387.23

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'
O O 0.0106 0.0060 '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

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

_cell_length_a                   8.3411(4)
_cell_length_b                   9.4833(5)
_cell_length_c                   14.6270(8)
_cell_angle_alpha                95.7490(10)
_cell_angle_beta                 105.7920(10)
_cell_angle_gamma                113.9930(10)
_cell_volume                     987.46(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5077
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            10282
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.20
_reflns_number_total             3522
_reflns_number_gt                2948
_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)+(0.0590P)²+0.1612P] 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         3522
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
B1 B 0.3940(2) 0.26105(17) 0.25016(11) 0.0406(3) Uani 1 1 d . . .
N1 N 0.35699(15) 0.41694(12) 0.25311(8) 0.0406(3) Uani 1 1 d . . .
N3 N 0.52327(16) 0.29307(12) 0.35722(8) 0.0424(3) Uani 1 1 d . . .
N2 N 0.61329(16) 0.56992(13) 0.40303(9) 0.0445(3) Uani 1 1 d . . .
O1 O 0.51554(18) 0.04692(12) 0.36336(8) 0.0662(3) Uani 1 1 d . . .
C5 C 0.47457(19) 0.55731(15) 0.32093(10) 0.0411(3) Uani 1 1 d . . .
C6 C 0.62713(18) 0.44273(15) 0.41795(9) 0.0396(3) Uani 1 1 d . . .
C20 C 0.50407(18) 0.26386(15) 0.17381(9) 0.0403(3) Uani 1 1 d . . .
C7 C 0.75909(19) 0.43653(16) 0.50550(10) 0.0422(3) Uani 1 1 d . . .
C14 C 0.1956(2) 0.10594(15) 0.22424(10) 0.0450(3) Uani 1 1 d . . .
C2 C 0.1915(2) 0.54334(18) 0.16449(11) 0.0522(4) Uani 1 1 d . . .
H2 H 0.0941 0.5358 0.1115 0.063 Uiso 1 1 calc R . .
C1 C 0.2171(2) 0.41212(17) 0.17797(10) 0.0478(3) Uani 1 1 d . . .
H1 H 0.1344 0.3153 0.1333 0.057 Uiso 1 1 calc R . .
C4 C 0.4530(2) 0.69348(16) 0.30920(11) 0.0481(3) Uani 1 1 d . . .
H4 H 0.5345 0.7894 0.3550 0.058 Uiso 1 1 calc R . .
C25 C 0.5617(2) 0.14602(17) 0.15930(11) 0.0520(4) Uani 1 1 d . . .
H25 H 0.5333 0.0659 0.1928 0.062 Uiso 1 1 calc R . .
C13 C 0.5787(2) 0.18685(16) 0.40009(10) 0.0463(3) Uani 1 1 d . . .
C12 C 0.7294(2) 0.28032(16) 0.49568(10) 0.0445(3) Uani 1 1 d . . .
C21 C 0.5526(2) 0.38002(17) 0.12167(11) 0.0504(4) Uani 1 1 d . . .
H21 H 0.5196 0.4618 0.1299 0.061 Uiso 1 1 calc R . .
C3 C 0.3138(2) 0.68772(17) 0.23140(12) 0.0526(4) Uani 1 1 d . . .
H3 H 0.3011 0.7791 0.2234 0.063 Uiso 1 1 calc R . .
C9 C 1.0036(2) 0.5100(2) 0.65601(11) 0.0568(4) Uani 1 1 d . . .
H9 H 1.0973 0.5867 0.7110 0.068 Uiso 1 1 calc R . .
C11 C 0.8356(2) 0.2360(2) 0.56555(11) 0.0546(4) Uani 1 1 d . . .
H11 H 0.8151 0.1309 0.5590 0.065 Uiso 1 1 calc R . .
C23 C 0.7017(2) 0.2613(2) 0.04531(12) 0.0603(4) Uani 1 1 d . . .
H23 H 0.7658 0.2601 0.0025 0.072 Uiso 1 1 calc R . .
C15 C 0.1045(2) 0.07987(18) 0.29268(13) 0.0590(4) Uani 1 1 d . . .
H15 H 0.1648 0.1468 0.3551 0.071 Uiso 1 1 calc R . .
C22 C 0.6484(2) 0.3786(2) 0.05790(12) 0.0612(4) Uani 1 1 d . . .
H22 H 0.6766 0.4576 0.0236 0.073 Uiso 1 1 calc R . .
C10 C 0.9743(2) 0.3546(2) 0.64604(11) 0.0597(4) Uani 1 1 d . . .
H10 H 1.0490 0.3287 0.6942 0.072 Uiso 1 1 calc R . .
C8 C 0.8965(2) 0.55440(18) 0.58599(10) 0.0496(4) Uani 1 1 d . . .
H8 H 0.9163 0.6593 0.5929 0.060 Uiso 1 1 calc R . .
C19 C 0.1000(2) -0.00173(18) 0.13361(12) 0.0586(4) Uani 1 1 d . . .
H19 H 0.1564 0.0095 0.0862 0.070 Uiso 1 1 calc R . .
C24 C 0.6595(2) 0.1455(2) 0.09655(12) 0.0597(4) Uani 1 1 d . . .
H24 H 0.6968 0.0663 0.0891 0.072 Uiso 1 1 calc R . .
C18 C -0.0768(3) -0.1252(2) 0.11177(15) 0.0753(6) Uani 1 1 d . . .
H18 H -0.1368 -0.1955 0.0504 0.090 Uiso 1 1 calc R . .
C17 C -0.1640(3) -0.1448(2) 0.17941(18) 0.0809(6) Uani 1 1 d . . .
H17 H -0.2840 -0.2267 0.1639 0.097 Uiso 1 1 calc R . .
C16 C -0.0736(3) -0.0432(2) 0.26993(17) 0.0752(5) Uani 1 1 d . . .
H16 H -0.1317 -0.0565 0.3166 0.090 Uiso 1 1 calc R . .


_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
B1 N3 1.5579(18) . ?
B1 C14 1.616(2) . ?
B1 C20 1.623(2) . ?
B1 N1 1.6273(18) . ?
N1 C1 1.3490(18) . ?
N1 C5 1.3646(17) . ?
N3 C6 1.3720(16) . ?
N3 C13 1.4033(18) . ?
N2 C6 1.2915(17) . ?
N2 C5 1.3776(18) . ?
O1 C13 1.2090(16) . ?
C5 C4 1.3950(19) . ?
C6 C7 1.468(2) . ?
C20 C21 1.3903(19) . ?
C20 C25 1.4034(19) . ?
C7 C8 1.382(2) . ?
C7 C12 1.3843(19) . ?
C14 C19 1.388(2) . ?
C14 C15 1.397(2) . ?
C2 C1 1.370(2) . ?
C2 C3 1.388(2) . ?
C4 C3 1.365(2) . ?
C25 C24 1.385(2) . ?
C13 C12 1.487(2) . ?
C12 C11 1.379(2) . ?
C21 C22 1.386(2) . ?
C9 C10 1.377(2) . ?
C9 C8 1.385(2) . ?
C11 C10 1.387(2) . ?
C23 C22 1.369(2) . ?
C23 C24 1.373(2) . ?
C15 C16 1.387(2) . ?
C19 C18 1.383(2) . ?
C18 C17 1.364(3) . ?
C17 C16 1.364(3) . ?

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
N3 B1 C14 111.35(11) . . ?
N3 B1 C20 111.08(12) . . ?
C14 B1 C20 115.74(11) . . ?
N3 B1 N1 102.32(10) . . ?
C14 B1 N1 108.17(11) . . ?
C20 B1 N1 107.18(10) . . ?
C1 N1 C5 118.77(12) . . ?
C1 N1 B1 117.83(11) . . ?
C5 N1 B1 122.86(11) . . ?
C6 N3 C13 109.52(11) . . ?
C6 N3 B1 122.47(11) . . ?
C13 N3 B1 127.05(11) . . ?
C6 N2 C5 118.52(11) . . ?
N1 C5 N2 122.36(12) . . ?
N1 C5 C4 119.72(13) . . ?
N2 C5 C4 117.90(12) . . ?
N2 C6 N3 126.85(13) . . ?
N2 C6 C7 124.37(12) . . ?
N3 C6 C7 108.77(11) . . ?
C21 C20 C25 115.64(13) . . ?
C21 C20 B1 124.44(12) . . ?
C25 C20 B1 119.89(12) . . ?
C8 C7 C12 121.20(14) . . ?
C8 C7 C6 131.42(13) . . ?
C12 C7 C6 107.36(11) . . ?
C19 C14 C15 116.04(14) . . ?
C19 C14 B1 123.76(13) . . ?
C15 C14 B1 120.07(13) . . ?
C1 C2 C3 118.69(14) . . ?
N1 C1 C2 122.96(13) . . ?
C3 C4 C5 120.83(14) . . ?
C24 C25 C20 121.96(14) . . ?
O1 C13 N3 125.14(13) . . ?
O1 C13 C12 127.89(14) . . ?
N3 C13 C12 106.96(11) . . ?
C11 C12 C7 121.48(13) . . ?
C11 C12 C13 131.08(14) . . ?
C7 C12 C13 107.39(12) . . ?
C22 C21 C20 122.51(14) . . ?
C4 C3 C2 118.97(14) . . ?
C10 C9 C8 121.44(14) . . ?
C12 C11 C10 117.30(15) . . ?
C22 C23 C24 119.36(16) . . ?
C16 C15 C14 121.74(17) . . ?
C23 C22 C21 120.18(15) . . ?
C9 C10 C11 121.27(15) . . ?
C7 C8 C9 117.31(15) . . ?
C18 C19 C14 121.88(17) . . ?
C23 C24 C25 120.33(15) . . ?
C17 C18 C19 120.61(18) . . ?
C16 C17 C18 119.37(17) . . ?
C17 C16 C15 120.33(19) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.030
