# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1OC
_database_code_depnum_ccdc_archive 'CCDC 1037296'
_audit_update_record             
;
2014-12-03 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H16 B F10 N O2'
_chemical_formula_weight         611.24

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   11.0372(7)
_cell_length_b                   11.6357(7)
_cell_length_c                   11.8660(7)
_cell_angle_alpha                111.3160(10)
_cell_angle_beta                 103.8310(10)
_cell_angle_gamma                100.2430(10)
_cell_volume                     1318.13(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7933
_cell_measurement_theta_min      2.271
_cell_measurement_theta_max      25.1475

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9486
_exptl_absorpt_correction_T_max  0.9829
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7932
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.44
_reflns_number_total             4837
_reflns_number_gt                3548
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SHELXS-97 (Sheldrick, 1990)'
_computing_cell_refinement       'SHELXS-97 (Sheldrick, 1990)'
_computing_data_reduction        'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0671P)²+0.9582P] 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     SHELXL
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4837
_refine_ls_number_parameters     367
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1484
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.018
_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
B B 0.6040(3) 0.8270(3) 0.8744(3) 0.0379(7) Uani 1 1 d . . .
O1 O 0.60519(17) 0.95340(16) 0.87044(17) 0.0426(5) Uani 1 1 d . . .
O2 O 0.69181(17) 0.85207(16) 1.00282(16) 0.0401(4) Uani 1 1 d . . .
C1 C 0.6012(3) 1.1705(3) 0.8360(3) 0.0637(9) Uani 1 1 d . . .
H1 H 0.5233 1.1131 0.8229 0.076 Uiso 1 1 calc R . .
C2 C 0.5986(5) 1.2749(4) 0.8081(4) 0.0883(13) Uani 1 1 d . . .
H2 H 0.5194 1.2892 0.7781 0.106 Uiso 1 1 calc R . .
C3 C 0.7138(5) 1.3583(4) 0.8248(4) 0.0891(13) Uani 1 1 d . . .
H3 H 0.7122 1.4285 0.8049 0.107 Uiso 1 1 calc R . .
C4 C 0.8309(4) 1.3383(3) 0.8705(4) 0.0743(11) Uani 1 1 d . . .
H4 H 0.9081 1.3941 0.8802 0.089 Uiso 1 1 calc R . .
C5 C 0.8348(3) 1.2360(3) 0.9023(3) 0.0561(8) Uani 1 1 d . . .
H5 H 0.9146 1.2246 0.9361 0.067 Uiso 1 1 calc R . .
C6 C 0.7196(3) 1.1502(2) 0.8840(2) 0.0440(6) Uani 1 1 d . . .
C7 C 0.7193(3) 1.0405(2) 0.9187(2) 0.0384(6) Uani 1 1 d . . .
C8 C 0.8238(3) 1.0306(2) 1.0000(2) 0.0407(6) Uani 1 1 d . . .
H8 H 0.9075 1.0826 1.0205 0.049 Uiso 1 1 calc R . .
C9 C 0.8037(2) 0.9414(2) 1.0520(2) 0.0368(6) Uani 1 1 d . . .
C10 C 0.8954(3) 0.9418(2) 1.1607(2) 0.0400(6) Uani 1 1 d . . .
C11 C 1.0159(3) 1.0372(3) 1.2317(3) 0.0485(7) Uani 1 1 d . . .
H11 H 1.0366 1.1060 1.2107 0.058 Uiso 1 1 calc R . .
C12 C 1.1032(3) 1.0314(3) 1.3307(3) 0.0578(8) Uani 1 1 d . . .
H12 H 1.1817 1.0968 1.3760 0.069 Uiso 1 1 calc R . .
C13 C 1.0776(3) 0.9287(3) 1.3664(3) 0.0547(8) Uani 1 1 d . . .
C14 C 0.9549(3) 0.8359(3) 1.2977(3) 0.0567(8) Uani 1 1 d . . .
H14 H 0.9323 0.7685 1.3205 0.068 Uiso 1 1 calc R . .
C15 C 0.8686(3) 0.8424(3) 1.1989(3) 0.0503(7) Uani 1 1 d . . .
H15 H 0.7888 0.7785 1.1551 0.060 Uiso 1 1 calc R . .
C16 C 1.2949(5) 1.0122(5) 1.5273(5) 0.123(2) Uani 1 1 d U . .
H16A H 1.3390 1.0133 1.4669 0.185 Uiso 1 1 calc R . .
H16B H 1.3447 0.9891 1.5894 0.185 Uiso 1 1 calc R . .
H16C H 1.2858 1.0962 1.5699 0.185 Uiso 1 1 calc R . .
C17 C 1.1407(5) 0.8106(5) 1.4933(4) 0.1046(16) Uani 1 1 d U . .
H17A H 1.0698 0.8124 1.5270 0.157 Uiso 1 1 calc R . .
H17B H 1.2172 0.8166 1.5567 0.157 Uiso 1 1 calc R . .
H17C H 1.1178 0.7314 1.4181 0.157 Uiso 1 1 calc R . .
C18 C 0.45663(12) 0.74313(14) 0.85357(17) 0.0372(6) Uani 1 1 d G . .
C19 C 0.44936(13) 0.63068(16) 0.87121(19) 0.0463(7) Uani 1 1 d G . .
C20 C 0.32870(16) 0.54955(14) 0.8483(2) 0.0540(8) Uani 1 1 d G . .
C21 C 0.21531(13) 0.58088(16) 0.80784(19) 0.0509(7) Uani 1 1 d G . .
C22 C 0.22258(12) 0.69333(16) 0.79020(18) 0.0457(7) Uani 1 1 d G . .
C23 C 0.34324(15) 0.77446(13) 0.81307(17) 0.0399(6) Uani 1 1 d G . .
C24 C 0.65331(17) 0.74052(15) 0.75534(13) 0.0397(6) Uani 1 1 d G . .
C25 C 0.74860(16) 0.67898(17) 0.77249(14) 0.0453(7) Uani 1 1 d G . .
C26 C 0.77422(17) 0.59873(18) 0.66700(19) 0.0565(8) Uani 1 1 d G . .
C27 C 0.7045(2) 0.58004(19) 0.54435(16) 0.0698(10) Uani 1 1 d G . .
C28 C 0.6092(2) 0.6416(2) 0.52719(12) 0.0659(9) Uani 1 1 d G . .
C29 C 0.58362(17) 0.72183(18) 0.63268(17) 0.0514(7) Uani 1 1 d G . .
F1 F 0.55151(17) 0.59446(17) 0.9044(2) 0.0677(6) Uani 1 1 d . . .
F2 F 0.3202(2) 0.44160(19) 0.8632(2) 0.0876(8) Uani 1 1 d . . .
F3 F 0.09928(18) 0.50165(19) 0.7846(2) 0.0795(6) Uani 1 1 d . . .
F4 F 0.11393(16) 0.72013(17) 0.74665(19) 0.0672(5) Uani 1 1 d . . .
F5 F 0.34312(16) 0.87803(15) 0.79399(17) 0.0545(5) Uani 1 1 d . . .
F6 F 0.81904(18) 0.69304(17) 0.88451(17) 0.0638(5) Uani 1 1 d . . .
F7 F 0.8627(2) 0.5368(2) 0.6833(2) 0.0851(7) Uani 1 1 d . . .
F8 F 0.7305(3) 0.5021(3) 0.4442(2) 0.1170(10) Uani 1 1 d . . .
F9 F 0.5438(3) 0.6224(3) 0.40920(19) 0.1053(9) Uani 1 1 d . . .
F10 F 0.4911(2) 0.7736(2) 0.60992(17) 0.0734(6) Uani 1 1 d . . .
N N 1.1669(3) 0.9186(3) 1.4602(3) 0.0787(9) Uani 1 1 d U . .


_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
B O1 1.487(3) . ?
B O2 1.488(3) . ?
B C18 1.652(3) . ?
B C24 1.683(3) . ?
O1 C7 1.311(3) . ?
O2 C9 1.305(3) . ?
C1 C2 1.373(4) . ?
C1 C6 1.393(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.477(3) . ?
C7 C8 1.368(4) . ?
C8 C9 1.398(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.435(4) . ?
C10 C15 1.398(4) . ?
C10 C11 1.403(4) . ?
C11 C12 1.361(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.412(4) . ?
C12 H12 0.9300 . ?
C13 N 1.354(4) . ?
C13 C14 1.407(4) . ?
C14 C15 1.358(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N 1.450(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N 1.449(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.3900 . ?
C18 C23 1.3900 . ?
C19 F1 1.297(2) . ?
C19 C20 1.3900 . ?
C20 F2 1.321(2) . ?
C20 C21 1.3900 . ?
C21 F3 1.339(2) . ?
C21 C22 1.3900 . ?
C22 F4 1.325(2) . ?
C22 C23 1.3900 . ?
C23 F5 1.3048(18) . ?
C24 C25 1.3900 . ?
C24 C29 1.3900 . ?
C25 F6 1.304(2) . ?
C25 C26 1.3900 . ?
C26 F7 1.331(2) . ?
C26 C27 1.3900 . ?
C27 F8 1.337(3) . ?
C27 C28 1.3900 . ?
C28 F9 1.328(2) . ?
C28 C29 1.3900 . ?
C29 F10 1.297(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 B O2 108.1(2) . . ?
O1 B C18 112.0(2) . . ?
O2 B C18 108.2(2) . . ?
O1 B C24 108.6(2) . . ?
O2 B C24 112.0(2) . . ?
C18 B C24 107.99(18) . . ?
C7 O1 B 116.5(2) . . ?
C9 O2 B 118.4(2) . . ?
C2 C1 C6 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 121.7(3) . . ?
C1 C6 C7 119.1(3) . . ?
O1 C7 C8 121.1(2) . . ?
O1 C7 C6 113.9(2) . . ?
C8 C7 C6 124.9(2) . . ?
C7 C8 C9 119.3(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
O2 C9 C8 119.1(2) . . ?
O2 C9 C10 115.6(2) . . ?
C8 C9 C10 125.2(2) . . ?
C15 C10 C11 116.5(2) . . ?
C15 C10 C9 120.3(2) . . ?
C11 C10 C9 123.2(2) . . ?
C12 C11 C10 121.6(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 121.7(3) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
N C13 C14 121.7(3) . . ?
N C13 C12 122.0(3) . . ?
C14 C13 C12 116.3(3) . . ?
C15 C14 C13 121.5(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 122.3(3) . . ?
C14 C15 H15 118.9 . . ?
C10 C15 H15 118.9 . . ?
N C16 H16A 109.5 . . ?
N C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N C17 H17A 109.5 . . ?
N C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 120.0 . . ?
C19 C18 B 115.72(13) . . ?
C23 C18 B 124.16(13) . . ?
F1 C19 C18 122.58(13) . . ?
F1 C19 C20 117.37(13) . . ?
C18 C19 C20 120.0 . . ?
F2 C20 C19 120.64(14) . . ?
F2 C20 C21 119.35(14) . . ?
C19 C20 C21 120.0 . . ?
F3 C21 C22 120.26(14) . . ?
F3 C21 C20 119.74(14) . . ?
C22 C21 C20 120.0 . . ?
F4 C22 C21 119.74(13) . . ?
F4 C22 C23 120.20(13) . . ?
C21 C22 C23 120.0 . . ?
F5 C23 C22 116.89(13) . . ?
F5 C23 C18 123.11(13) . . ?
C22 C23 C18 120.0 . . ?
C25 C24 C29 120.0 . . ?
C25 C24 B 123.68(14) . . ?
C29 C24 B 116.02(14) . . ?
F6 C25 C24 123.53(15) . . ?
F6 C25 C26 116.46(15) . . ?
C24 C25 C26 120.0 . . ?
F7 C26 C25 119.90(17) . . ?
F7 C26 C27 120.06(17) . . ?
C25 C26 C27 120.0 . . ?
F8 C27 C28 121.0(2) . . ?
F8 C27 C26 119.0(2) . . ?
C28 C27 C26 120.0 . . ?
F9 C28 C29 120.97(19) . . ?
F9 C28 C27 119.03(19) . . ?
C29 C28 C27 120.0 . . ?
F10 C29 C28 116.96(15) . . ?
F10 C29 C24 123.01(15) . . ?
C28 C29 C24 120.0 . . ?
C13 N C16 121.3(3) . . ?
C13 N C17 121.4(3) . . ?
C16 N C17 117.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.44
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_1RC
_database_code_depnum_ccdc_archive 'CCDC 1037297'
_audit_update_record             
;
2014-12-03 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H16 B F10 N O2'
_chemical_formula_weight         611.24

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           Triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   10.4884(8)
_cell_length_b                   11.0467(8)
_cell_length_c                   11.5358(9)
_cell_angle_alpha                95.2680(10)
_cell_angle_beta                 98.3540(10)
_cell_angle_gamma                99.4260(10)
_cell_volume                     1295.34(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1951
_cell_measurement_theta_min      2.443
_cell_measurement_theta_max      24.7375

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6313
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4504
_reflns_number_gt                3377
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SHELXS-97 (Sheldrick, 1990)'
_computing_cell_refinement       'SHELXS-97 (Sheldrick, 1990)'
_computing_data_reduction        'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.1212P)²+0.3146P] 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         4504
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.2002
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.004

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
N N 1.0394(3) 0.0983(3) 0.6914(2) 0.0497(7) Uani 1 1 d . . .
B B 0.4847(3) 0.1840(3) 0.2026(3) 0.0340(8) Uani 1 1 d . . .
O1 O 0.40360(19) 0.06178(19) 0.15108(17) 0.0374(5) Uani 1 1 d . . .
O2 O 0.60815(19) 0.16134(19) 0.27220(18) 0.0364(5) Uani 1 1 d . . .
C1 C 0.2168(3) -0.1368(3) 0.0640(3) 0.0533(9) Uani 1 1 d . . .
H1 H 0.2379 -0.0747 0.0171 0.064 Uiso 1 1 calc R . .
C2 C 0.1138(4) -0.2322(4) 0.0221(4) 0.0717(12) Uani 1 1 d . . .
H2 H 0.0657 -0.2342 -0.0526 0.086 Uiso 1 1 calc R . .
C3 C 0.0816(4) -0.3257(4) 0.0914(5) 0.0692(13) Uani 1 1 d . . .
H3 H 0.0124 -0.3905 0.0631 0.083 Uiso 1 1 calc R . .
C4 C 0.1529(4) -0.3215(3) 0.2023(4) 0.0584(10) Uani 1 1 d . . .
H4 H 0.1306 -0.3834 0.2491 0.070 Uiso 1 1 calc R . .
C5 C 0.2567(3) -0.2268(3) 0.2448(3) 0.0459(8) Uani 1 1 d . . .
H5 H 0.3047 -0.2257 0.3194 0.055 Uiso 1 1 calc R . .
C6 C 0.2899(3) -0.1321(3) 0.1758(3) 0.0388(7) Uani 1 1 d . . .
C7 C 0.3979(3) -0.0275(3) 0.2191(3) 0.0335(7) Uani 1 1 d . . .
C8 C 0.4899(3) -0.0221(3) 0.3179(3) 0.0356(7) Uani 1 1 d . . .
H8 H 0.4779 -0.0795 0.3712 0.043 Uiso 1 1 calc R . .
C9 C 0.6023(3) 0.0706(3) 0.3382(2) 0.0321(6) Uani 1 1 d . . .
C10 C 0.7164(3) 0.0734(3) 0.4248(3) 0.0338(7) Uani 1 1 d . . .
C11 C 0.7293(3) -0.0224(3) 0.4960(3) 0.0370(7) Uani 1 1 d . . .
H11 H 0.6639 -0.0923 0.4840 0.044 Uiso 1 1 calc R . .
C12 C 0.8349(3) -0.0154(3) 0.5818(3) 0.0401(7) Uani 1 1 d . . .
H12 H 0.8397 -0.0802 0.6274 0.048 Uiso 1 1 calc R . .
C13 C 0.9371(3) 0.0879(3) 0.6029(3) 0.0397(7) Uani 1 1 d . . .
C14 C 0.9263(3) 0.1832(3) 0.5282(3) 0.0407(7) Uani 1 1 d . . .
H14 H 0.9933 0.2516 0.5378 0.049 Uiso 1 1 calc R . .
C15 C 0.8199(3) 0.1758(3) 0.4436(3) 0.0377(7) Uani 1 1 d . . .
H15 H 0.8152 0.2397 0.3969 0.045 Uiso 1 1 calc R . .
C16 C 1.0447(4) 0.0064(4) 0.7739(3) 0.0649(11) Uani 1 1 d . . .
H16A H 0.9645 -0.0065 0.8055 0.097 Uiso 1 1 calc R . .
H16B H 1.1169 0.0350 0.8370 0.097 Uiso 1 1 calc R . .
H16C H 1.0564 -0.0700 0.7335 0.097 Uiso 1 1 calc R . .
C17 C 1.1432(4) 0.2060(4) 0.7133(4) 0.0673(11) Uani 1 1 d . . .
H17A H 1.1864 0.2119 0.6456 0.101 Uiso 1 1 calc R . .
H17B H 1.2053 0.1983 0.7809 0.101 Uiso 1 1 calc R . .
H17C H 1.1065 0.2789 0.7280 0.101 Uiso 1 1 calc R . .
C18 C 0.3987(3) 0.2556(3) 0.2865(3) 0.0347(7) Uani 1 1 d . . .
C19 C 0.4372(3) 0.3066(3) 0.4029(3) 0.0390(7) Uani 1 1 d . . .
C20 C 0.3624(4) 0.3713(3) 0.4667(3) 0.0451(8) Uani 1 1 d . . .
C21 C 0.2401(3) 0.3858(3) 0.4129(3) 0.0474(8) Uani 1 1 d . . .
C22 C 0.1966(3) 0.3371(3) 0.2982(3) 0.0468(8) Uani 1 1 d . . .
C23 C 0.2746(3) 0.2733(3) 0.2378(3) 0.0390(7) Uani 1 1 d . . .
C24 C 0.52658(18) 0.26821(16) 0.09776(14) 0.0342(7) Uani 1 1 d G . .
C25 C 0.62427(18) 0.37173(17) 0.13286(13) 0.0375(7) Uani 1 1 d G . .
C26 C 0.66402(18) 0.44749(15) 0.05017(18) 0.0434(8) Uani 1 1 d G . .
C27 C 0.6061(2) 0.41973(17) -0.06762(16) 0.0421(8) Uani 1 1 d G . .
C28 C 0.50841(19) 0.31621(19) -0.10272(12) 0.0392(7) Uani 1 1 d G . .
C29 C 0.46865(17) 0.24045(16) -0.02003(16) 0.0375(7) Uani 1 1 d G . .
F1 F 0.5553(2) 0.29680(19) 0.46300(16) 0.0541(5) Uani 1 1 d . . .
F2 F 0.4064(2) 0.4175(2) 0.57912(17) 0.0640(6) Uani 1 1 d . . .
F3 F 0.1661(2) 0.4480(2) 0.4731(2) 0.0693(7) Uani 1 1 d . . .
F4 F 0.07778(19) 0.3523(2) 0.2444(2) 0.0689(7) Uani 1 1 d . . .
F5 F 0.22584(17) 0.22919(19) 0.12412(17) 0.0518(5) Uani 1 1 d . . .
F6 F 0.6796(2) 0.40480(18) 0.24308(16) 0.0527(5) Uani 1 1 d . . .
F7 F 0.7579(2) 0.54676(18) 0.0823(2) 0.0612(6) Uani 1 1 d . . .
F8 F 0.6433(2) 0.49305(19) -0.14806(19) 0.0596(6) Uani 1 1 d . . .
F9 F 0.4527(2) 0.2917(2) -0.21550(16) 0.0552(6) Uani 1 1 d . . .
F10 F 0.37715(18) 0.14361(18) -0.05978(16) 0.0490(5) 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
N C13 1.351(4) . ?
N C17 1.450(5) . ?
N C16 1.456(5) . ?
B O2 1.492(4) . ?
B O1 1.493(4) . ?
B C18 1.650(5) . ?
B C24 1.658(3) . ?
O1 C7 1.315(3) . ?
O2 C9 1.312(3) . ?
C1 C2 1.376(5) . ?
C1 C6 1.393(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.391(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.473(4) . ?
C7 C8 1.372(4) . ?
C8 C9 1.405(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.437(4) . ?
C10 C11 1.410(4) . ?
C10 C15 1.410(4) . ?
C11 C12 1.361(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.408(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.429(4) . ?
C14 C15 1.358(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.382(4) . ?
C18 C23 1.393(4) . ?
C19 F1 1.354(4) . ?
C19 C20 1.386(5) . ?
C20 F2 1.336(4) . ?
C20 C21 1.382(5) . ?
C21 F3 1.341(4) . ?
C21 C22 1.365(5) . ?
C22 F4 1.353(4) . ?
C22 C23 1.383(5) . ?
C23 F5 1.351(4) . ?
C24 C25 1.3900 . ?
C24 C29 1.3900 . ?
C25 F6 1.311(2) . ?
C25 C26 1.3900 . ?
C26 F7 1.332(2) . ?
C26 C27 1.3900 . ?
C27 F8 1.345(2) . ?
C27 C28 1.3900 . ?
C28 F9 1.330(2) . ?
C28 C29 1.3900 . ?
C29 F10 1.312(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
C13 N C17 121.3(3) . . ?
C13 N C16 121.2(3) . . ?
C17 N C16 117.3(3) . . ?
O2 B O1 108.1(2) . . ?
O2 B C18 111.6(2) . . ?
O1 B C18 108.0(2) . . ?
O2 B C24 107.3(2) . . ?
O1 B C24 111.2(2) . . ?
C18 B C24 110.7(2) . . ?
C7 O1 B 117.3(2) . . ?
C9 O2 B 119.0(2) . . ?
C2 C1 C6 120.8(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.1(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 119.5(3) . . ?
C5 C6 C7 121.8(3) . . ?
O1 C7 C8 121.1(3) . . ?
O1 C7 C6 113.9(3) . . ?
C8 C7 C6 124.9(3) . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
O2 C9 C8 119.0(3) . . ?
O2 C9 C10 115.8(2) . . ?
C8 C9 C10 125.2(3) . . ?
C11 C10 C15 117.2(3) . . ?
C11 C10 C9 122.5(3) . . ?
C15 C10 C9 120.3(3) . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
N C13 C12 121.8(3) . . ?
N C13 C14 121.2(3) . . ?
C12 C13 C14 116.9(3) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C10 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
N C16 H16A 109.5 . . ?
N C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N C17 H17A 109.5 . . ?
N C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 113.6(3) . . ?
C19 C18 B 127.3(3) . . ?
C23 C18 B 119.0(3) . . ?
F1 C19 C18 120.8(3) . . ?
F1 C19 C20 114.8(3) . . ?
C18 C19 C20 124.4(3) . . ?
F2 C20 C21 120.1(3) . . ?
F2 C20 C19 120.8(3) . . ?
C21 C20 C19 119.1(3) . . ?
F3 C21 C22 120.8(3) . . ?
F3 C21 C20 120.0(3) . . ?
C22 C21 C20 119.2(3) . . ?
F4 C22 C21 119.5(3) . . ?
F4 C22 C23 120.7(3) . . ?
C21 C22 C23 119.8(3) . . ?
F5 C23 C22 116.4(3) . . ?
F5 C23 C18 119.6(3) . . ?
C22 C23 C18 124.0(3) . . ?
C25 C24 C29 120.0 . . ?
C25 C24 B 116.61(16) . . ?
C29 C24 B 123.39(16) . . ?
F6 C25 C24 122.78(15) . . ?
F6 C25 C26 117.18(15) . . ?
C24 C25 C26 120.0 . . ?
F7 C26 C27 119.25(16) . . ?
F7 C26 C25 120.74(16) . . ?
C27 C26 C25 120.0 . . ?
F8 C27 C26 120.39(17) . . ?
F8 C27 C28 119.61(17) . . ?
C26 C27 C28 120.0 . . ?
F9 C28 C29 120.67(16) . . ?
F9 C28 C27 119.33(16) . . ?
C29 C28 C27 120.0 . . ?
F10 C29 C28 116.62(14) . . ?
F10 C29 C24 123.38(14) . . ?
C28 C29 C24 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.077

