# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_cc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        CB
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 B F2 N2 O'
_chemical_formula_weight         410.22

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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'

_cell_length_a                   14.306(3)
_cell_length_b                   10.163(2)
_cell_length_c                   13.511(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1964.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16381
_cell_measurement_theta_min      6.03
_cell_measurement_theta_max      54.94

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9855
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17919
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.45
_reflns_number_total             4403
_reflns_number_gt                3850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0610P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         4403
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_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
B1 B 0.05071(12) 0.1795(2) 0.37649(15) 0.0337(5) Uani 1 1 d . . .
C1 C 0.53049(12) 0.13092(15) -0.02260(11) 0.0282(4) Uani 1 1 d . . .
C2 C 0.48862(14) 0.23860(17) -0.06910(14) 0.0380(4) Uani 1 1 d . . .
H2A H 0.4275 0.2635 -0.0551 0.046 Uiso 1 1 calc R . .
C3 C 0.54322(17) 0.3068(2) -0.13755(14) 0.0485(6) Uani 1 1 d . . .
H3A H 0.5169 0.3776 -0.1711 0.058 Uiso 1 1 calc R . .
C4 C 0.63655(18) 0.2725(2) -0.15777(14) 0.0530(6) Uani 1 1 d . . .
H4A H 0.6704 0.3210 -0.2039 0.064 Uiso 1 1 calc R . .
C5 C 0.67888(15) 0.16721(19) -0.10988(14) 0.0439(5) Uani 1 1 d . . .
H5A H 0.7409 0.1456 -0.1226 0.053 Uiso 1 1 calc R . .
C6 C 0.62559(12) 0.09379(17) -0.04144(12) 0.0324(4) Uani 1 1 d . . .
C7 C 0.64577(10) -0.01900(17) 0.01952(12) 0.0297(4) Uani 1 1 d . . .
C8 C 0.72501(11) -0.10105(19) 0.03001(14) 0.0368(4) Uani 1 1 d . . .
H8A H 0.7787 -0.0861 -0.0072 0.044 Uiso 1 1 calc R . .
C9 C 0.72096(13) -0.2038(2) 0.09668(14) 0.0407(5) Uani 1 1 d . . .
H9A H 0.7728 -0.2578 0.1055 0.049 Uiso 1 1 calc R . .
C10 C 0.63876(13) -0.22766(19) 0.15156(14) 0.0386(4) Uani 1 1 d . . .
H10A H 0.6379 -0.2977 0.1959 0.046 Uiso 1 1 calc R . .
C11 C 0.55789(11) -0.14930(17) 0.14178(13) 0.0307(4) Uani 1 1 d . . .
H11A H 0.5040 -0.1667 0.1779 0.037 Uiso 1 1 calc R . .
C12 C 0.56268(11) -0.04487(15) 0.07552(12) 0.0253(3) Uani 1 1 d . . .
C13 C 0.40083(11) 0.05754(15) 0.09190(11) 0.0239(3) Uani 1 1 d . . .
C14 C 0.32101(11) 0.06913(15) 0.03115(12) 0.0279(3) Uani 1 1 d . . .
H14A H 0.3278 0.0668 -0.0373 0.033 Uiso 1 1 calc R . .
C15 C 0.23126(11) 0.08418(16) 0.07233(12) 0.0270(3) Uani 1 1 d . . .
H15A H 0.1795 0.0920 0.0311 0.032 Uiso 1 1 calc R . .
C16 C 0.21959(11) 0.08743(14) 0.17553(12) 0.0231(3) Uani 1 1 d . . .
C17 C 0.30030(10) 0.07425(14) 0.23524(11) 0.0227(3) Uani 1 1 d . . .
H17A H 0.2937 0.0756 0.3037 0.027 Uiso 1 1 calc R . .
C18 C 0.39020(11) 0.05923(15) 0.19447(11) 0.0238(3) Uani 1 1 d . . .
H18A H 0.4420 0.0505 0.2355 0.029 Uiso 1 1 calc R . .
C19 C 0.12500(10) 0.10647(15) 0.22200(11) 0.0228(3) Uani 1 1 d . . .
C20 C 0.04067(11) 0.10703(16) 0.17350(12) 0.0269(3) Uani 1 1 d . . .
H20A H 0.0405 0.1011 0.1048 0.032 Uiso 1 1 calc R . .
C21 C -0.04845(10) 0.11652(15) 0.22490(12) 0.0239(3) Uani 1 1 d . . .
C22 C -0.13660(11) 0.09181(16) 0.17914(13) 0.0292(4) Uani 1 1 d . . .
H22A H -0.1389 0.0717 0.1120 0.035 Uiso 1 1 calc R . .
C23 C -0.21930(11) 0.09733(16) 0.23351(14) 0.0314(4) Uani 1 1 d . . .
H23A H -0.2765 0.0810 0.2031 0.038 Uiso 1 1 calc R . .
C24 C -0.21524(11) 0.12754(16) 0.33384(14) 0.0301(4) Uani 1 1 d . . .
H24A H -0.2695 0.1319 0.3716 0.036 Uiso 1 1 calc R . .
C25 C -0.12849(11) 0.15101(16) 0.37629(13) 0.0287(3) Uani 1 1 d . . .
H25A H -0.1255 0.1711 0.4434 0.034 Uiso 1 1 calc R . .
N1 N 0.49306(9) 0.04664(13) 0.04936(9) 0.0263(3) Uani 1 1 d . . .
N2 N -0.04688(9) 0.14573(13) 0.32304(11) 0.0243(3) Uani 1 1 d . . .
O1 O 0.12840(7) 0.11951(13) 0.32097(8) 0.0307(3) Uani 1 1 d . . .
F1 F 0.04887(7) 0.12875(17) 0.46993(8) 0.0623(4) Uani 1 1 d . . .
F2 F 0.05923(7) 0.31478(13) 0.37685(11) 0.0592(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.364(3) . ?
B1 F2 1.381(3) . ?
B1 O1 1.473(2) . ?
B1 N2 1.609(2) . ?
C1 C2 1.397(3) . ?
C1 N1 1.402(2) . ?
C1 C6 1.435(2) . ?
C2 C3 1.395(3) . ?
C3 C4 1.407(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.412(2) . ?
C6 C7 1.441(3) . ?
C7 C8 1.414(2) . ?
C7 C12 1.433(2) . ?
C8 C9 1.380(3) . ?
C9 C10 1.411(3) . ?
C10 C11 1.411(2) . ?
C11 C12 1.390(2) . ?
C12 N1 1.408(2) . ?
C13 C18 1.394(2) . ?
C13 C14 1.411(2) . ?
C13 N1 1.443(2) . ?
C14 C15 1.408(2) . ?
C15 C16 1.405(2) . ?
C16 C17 1.415(2) . ?
C16 C19 1.504(2) . ?
C17 C18 1.407(2) . ?
C19 O1 1.3447(19) . ?
C19 C20 1.373(2) . ?
C20 C21 1.455(2) . ?
C21 N2 1.359(2) . ?
C21 C22 1.427(2) . ?
C22 C23 1.394(2) . ?
C23 C24 1.391(3) . ?
C24 C25 1.388(2) . ?
C25 N2 1.372(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
F1 B1 F2 112.01(18) . . ?
F1 B1 O1 109.25(16) . . ?
F2 B1 O1 110.32(16) . . ?
F1 B1 N2 108.56(15) . . ?
F2 B1 N2 106.88(15) . . ?
O1 B1 N2 109.77(14) . . ?
C2 C1 N1 128.81(16) . . ?
C2 C1 C6 122.20(15) . . ?
N1 C1 C6 108.94(15) . . ?
C3 C2 C1 116.58(19) . . ?
C2 C3 C4 122.5(2) . . ?
C5 C4 C3 120.94(18) . . ?
C4 C5 C6 118.5(2) . . ?
C5 C6 C1 119.30(18) . . ?
C5 C6 C7 133.38(18) . . ?
C1 C6 C7 107.32(13) . . ?
C8 C7 C12 120.25(16) . . ?
C8 C7 C6 133.38(15) . . ?
C12 C7 C6 106.35(14) . . ?
C9 C8 C7 118.53(16) . . ?
C8 C9 C10 120.52(16) . . ?
C11 C10 C9 122.50(19) . . ?
C12 C11 C10 116.79(16) . . ?
C11 C12 N1 129.14(14) . . ?
C11 C12 C7 121.39(15) . . ?
N1 C12 C7 109.45(14) . . ?
C18 C13 C14 119.26(14) . . ?
C18 C13 N1 119.77(14) . . ?
C14 C13 N1 120.97(13) . . ?
C15 C14 C13 121.15(14) . . ?
C16 C15 C14 120.23(15) . . ?
C15 C16 C17 117.82(15) . . ?
C15 C16 C19 121.62(14) . . ?
C17 C16 C19 120.55(13) . . ?
C18 C17 C16 122.20(14) . . ?
C13 C18 C17 119.35(15) . . ?
O1 C19 C20 120.39(14) . . ?
O1 C19 C16 113.28(13) . . ?
C20 C19 C16 126.29(14) . . ?
C19 C20 C21 122.85(15) . . ?
N2 C21 C22 118.42(14) . . ?
N2 C21 C20 117.76(14) . . ?
C22 C21 C20 123.78(15) . . ?
C23 C22 C21 120.98(15) . . ?
C24 C23 C22 119.15(15) . . ?
C25 C24 C23 118.55(15) . . ?
N2 C25 C24 122.51(15) . . ?
C1 N1 C12 107.91(13) . . ?
C1 N1 C13 125.34(13) . . ?
C12 N1 C13 126.68(13) . . ?
C21 N2 C25 120.39(14) . . ?
C21 N2 B1 119.92(13) . . ?
C25 N2 B1 119.65(13) . . ?
C19 O1 B1 121.33(13) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_database_code_depnum_ccdc_archive 'CCDC 1010373'
