# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 B F2 N3 O'
_chemical_formula_weight         443.29

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                   10.2704(4)
_cell_length_b                   10.7807(5)
_cell_length_c                   11.5645(6)
_cell_angle_alpha                73.4540(10)
_cell_angle_beta                 84.803(2)
_cell_angle_gamma                62.6970(10)
_cell_volume                     1089.48(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9483
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9483
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4264
_reflns_number_gt                2834
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0765P)²+0.4049P] 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     SHELXL
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4264
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_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 1.0815(3) -0.8501(3) -0.5301(2) 0.0449(7) Uani 1 1 d . . .
H1A H 1.1372 -0.9226 -0.5703 0.054 Uiso 1 1 calc R . .
C2 C 1.1514(3) -0.7968(3) -0.4755(2) 0.0412(6) Uani 1 1 d . . .
H2A H 1.2547 -0.8321 -0.4781 0.049 Uiso 1 1 calc R . .
C3 C 1.0696(3) -0.6918(3) -0.4172(2) 0.0367(6) Uani 1 1 d . . .
H3A H 1.1179 -0.6564 -0.3786 0.044 Uiso 1 1 calc R . .
C4 C 0.9169(2) -0.6362(2) -0.41378(19) 0.0302(5) Uani 1 1 d . . .
C5 C 0.8477(3) -0.6920(3) -0.4697(2) 0.0331(5) Uani 1 1 d . . .
C6 C 0.9304(3) -0.7984(3) -0.5266(2) 0.0427(6) Uani 1 1 d . . .
H6A H 0.8835 -0.8364 -0.5637 0.051 Uiso 1 1 calc R . .
C7 C 0.8344(2) -0.5217(2) -0.35604(19) 0.0292(5) Uani 1 1 d . . .
H7A H 0.8849 -0.4838 -0.3228 0.035 Uiso 1 1 calc R . .
C8 C 0.6160(2) -0.3576(2) -0.2917(2) 0.0297(5) Uani 1 1 d . . .
C9 C 0.6762(3) -0.3373(3) -0.1998(2) 0.0355(6) Uani 1 1 d . . .
H9A H 0.7754 -0.4003 -0.1720 0.043 Uiso 1 1 calc R . .
C10 C 0.5908(3) -0.2245(3) -0.1488(2) 0.0354(6) Uani 1 1 d . . .
H10A H 0.6322 -0.2117 -0.0856 0.042 Uiso 1 1 calc R . .
C11 C 0.4464(2) -0.1304(2) -0.1888(2) 0.0290(5) Uani 1 1 d . . .
C12 C 0.3873(2) -0.1534(3) -0.2793(2) 0.0312(5) Uani 1 1 d . . .
H12A H 0.2881 -0.0904 -0.3071 0.037 Uiso 1 1 calc R . .
C13 C 0.4697(3) -0.2659(3) -0.3296(2) 0.0333(6) Uani 1 1 d . . .
H13A H 0.4265 -0.2810 -0.3903 0.040 Uiso 1 1 calc R . .
C14 C 0.3549(2) -0.0103(2) -0.13424(19) 0.0273(5) Uani 1 1 d . . .
C15 C 0.3526(2) 0.1257(2) -0.1810(2) 0.0283(5) Uani 1 1 d . . .
C16 C 0.4410(3) 0.1720(3) -0.2666(2) 0.0326(5) Uani 1 1 d . . .
C17 C 0.5649(3) 0.0868(3) -0.3336(3) 0.0453(7) Uani 1 1 d . . .
H17A H 0.6016 0.1509 -0.3877 0.068 Uiso 1 1 calc R . .
H17B H 0.5307 0.0444 -0.3812 0.068 Uiso 1 1 calc R . .
H17C H 0.6439 0.0091 -0.2760 0.068 Uiso 1 1 calc R . .
C18 C 0.3934(3) 0.3169(3) -0.2737(2) 0.0391(6) Uani 1 1 d . . .
H18A H 0.4322 0.3777 -0.3236 0.047 Uiso 1 1 calc R . .
C19 C 0.2787(3) 0.3595(3) -0.1954(2) 0.0338(5) Uani 1 1 d . . .
C20 C 0.1929(3) 0.5048(3) -0.1743(3) 0.0466(7) Uani 1 1 d . . .
H20A H 0.0882 0.5377 -0.1890 0.070 Uiso 1 1 calc R . .
H20B H 0.2230 0.5739 -0.2294 0.070 Uiso 1 1 calc R . .
H20C H 0.2109 0.4988 -0.0907 0.070 Uiso 1 1 calc R . .
C21 C 0.1093(3) 0.0267(3) 0.1046(2) 0.0317(5) Uani 1 1 d . . .
C22 C -0.0027(3) 0.1169(3) 0.1752(2) 0.0429(6) Uani 1 1 d . . .
H22A H -0.0882 0.1907 0.1219 0.064 Uiso 1 1 calc R . .
H22B H 0.0386 0.1645 0.2105 0.064 Uiso 1 1 calc R . .
H22C H -0.0328 0.0551 0.2398 0.064 Uiso 1 1 calc R . .
C23 C 0.1686(3) -0.1236(3) 0.1241(2) 0.0363(6) Uani 1 1 d . . .
H23A H 0.1445 -0.1873 0.1872 0.044 Uiso 1 1 calc R . .
C24 C 0.2675(3) -0.1645(3) 0.0367(2) 0.0333(5) Uani 1 1 d . . .
C25 C 0.3564(3) -0.3179(3) 0.0304(2) 0.0431(6) Uani 1 1 d . . .
H25A H 0.3146 -0.3789 0.0817 0.065 Uiso 1 1 calc R . .
H25B H 0.4578 -0.3538 0.0587 0.065 Uiso 1 1 calc R . .
H25C H 0.3551 -0.3212 -0.0532 0.065 Uiso 1 1 calc R . .
C26 C 0.2697(2) -0.0340(2) -0.03768(19) 0.0277(5) Uani 1 1 d . . .
N1 N 0.6948(2) -0.4701(2) -0.34871(17) 0.0322(5) Uani 1 1 d . . .
N2 N 0.25495(19) 0.2439(2) -0.13833(17) 0.0286(4) Uani 1 1 d . . .
N3 N 0.17071(19) 0.0811(2) 0.00793(16) 0.0277(4) Uani 1 1 d . . .
O1 O 0.70005(19) -0.6426(2) -0.46916(17) 0.0431(5) Uani 1 1 d . . .
B1 B 0.1291(3) 0.2428(3) -0.0535(2) 0.0291(6) Uani 1 1 d . . .
F1 F -0.00303(14) 0.31105(15) -0.12062(13) 0.0396(4) Uani 1 1 d . . .
F2 F 0.11579(14) 0.31427(15) 0.03220(12) 0.0381(4) Uani 1 1 d . . .
H1D H 0.667(4) -0.566(4) -0.423(3) 0.082(11) Uiso 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
C1 C2 1.384(4) . ?
C1 C6 1.388(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.400(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.408(3) . ?
C4 C7 1.447(3) . ?
C5 O1 1.357(3) . ?
C5 C6 1.380(3) . ?
C6 H6A 0.9500 . ?
C7 N1 1.283(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.390(3) . ?
C8 C13 1.392(3) . ?
C8 N1 1.421(3) . ?
C9 C10 1.390(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.389(3) . ?
C11 C14 1.483(3) . ?
C12 C13 1.377(3) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C26 1.395(3) . ?
C14 C15 1.400(3) . ?
C15 N2 1.404(3) . ?
C15 C16 1.424(3) . ?
C16 C18 1.386(3) . ?
C16 C17 1.489(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.402(3) . ?
C18 H18A 0.9500 . ?
C19 N2 1.353(3) . ?
C19 C20 1.484(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N3 1.352(3) . ?
C21 C23 1.400(3) . ?
C21 C22 1.480(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.380(3) . ?
C23 H23A 0.9500 . ?
C24 C26 1.434(3) . ?
C24 C25 1.498(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 N3 1.404(3) . ?
N2 B1 1.553(3) . ?
N3 B1 1.546(3) . ?
O1 H1D 1.02(4) . ?
B1 F2 1.381(3) . ?
B1 F1 1.391(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
C2 C1 C6 120.4(2) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 C7 119.7(2) . . ?
C5 C4 C7 121.9(2) . . ?
O1 C5 C6 119.0(2) . . ?
O1 C5 C4 121.1(2) . . ?
C6 C5 C4 119.9(2) . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
N1 C7 C4 121.5(2) . . ?
N1 C7 H7A 119.2 . . ?
C4 C7 H7A 119.2 . . ?
C9 C8 C13 119.2(2) . . ?
C9 C8 N1 123.7(2) . . ?
C13 C8 N1 117.0(2) . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 C12 118.4(2) . . ?
C10 C11 C14 121.2(2) . . ?
C12 C11 C14 120.4(2) . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C12 C13 C8 120.2(2) . . ?
C12 C13 H13A 119.9 . . ?
C8 C13 H13A 119.9 . . ?
C26 C14 C15 120.7(2) . . ?
C26 C14 C11 119.1(2) . . ?
C15 C14 C11 120.1(2) . . ?
C14 C15 N2 120.42(19) . . ?
C14 C15 C16 131.4(2) . . ?
N2 C15 C16 108.1(2) . . ?
C18 C16 C15 105.9(2) . . ?
C18 C16 C17 124.7(2) . . ?
C15 C16 C17 129.3(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 109.0(2) . . ?
C16 C18 H18A 125.5 . . ?
C19 C18 H18A 125.5 . . ?
N2 C19 C18 108.7(2) . . ?
N2 C19 C20 123.2(2) . . ?
C18 C19 C20 128.1(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C23 109.1(2) . . ?
N3 C21 C22 123.6(2) . . ?
C23 C21 C22 127.4(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 109.0(2) . . ?
C24 C23 H23A 125.5 . . ?
C21 C23 H23A 125.5 . . ?
C23 C24 C26 106.0(2) . . ?
C23 C24 C25 124.4(2) . . ?
C26 C24 C25 129.5(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C14 C26 N3 120.5(2) . . ?
C14 C26 C24 131.6(2) . . ?
N3 C26 C24 107.75(19) . . ?
C7 N1 C8 120.6(2) . . ?
C19 N2 C15 108.23(19) . . ?
C19 N2 B1 127.17(19) . . ?
C15 N2 B1 124.11(19) . . ?
C21 N3 C26 108.15(19) . . ?
C21 N3 B1 127.19(18) . . ?
C26 N3 B1 124.30(18) . . ?
C5 O1 H1D 103(2) . . ?
F2 B1 F1 108.75(19) . . ?
F2 B1 N3 110.39(19) . . ?
F1 B1 N3 110.94(19) . . ?
F2 B1 N2 110.93(19) . . ?
F1 B1 N2 109.83(19) . . ?
N3 B1 N2 105.99(18) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 1000809'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 B F2 N3 O'
_chemical_formula_weight         493.35

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                   9.2908(7)
_cell_length_b                   10.8702(8)
_cell_length_c                   13.9066(12)
_cell_angle_alpha                102.090(7)
_cell_angle_beta                 94.075(7)
_cell_angle_gamma                114.538(7)
_cell_volume                     1229.41(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8504
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8504
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4842
_reflns_number_gt                3787
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0511P)²+0.1344P] 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         4842
_refine_ls_number_parameters     342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 1.26990(19) 1.93406(16) 1.00886(12) 0.0372(4) Uani 1 1 d . . .
H1A H 1.3558 2.0102 1.0527 0.045 Uiso 1 1 calc R . .
C2 C 1.1561(2) 1.95565(17) 0.95820(13) 0.0421(4) Uani 1 1 d . . .
H2A H 1.1647 2.0457 0.9662 0.050 Uiso 1 1 calc R . .
C3 C 1.0250(2) 1.84000(18) 0.89337(13) 0.0418(4) Uani 1 1 d . . .
H3A H 0.9455 1.8538 0.8592 0.050 Uiso 1 1 calc R . .
C4 C 1.01265(18) 1.70800(16) 0.87985(11) 0.0317(4) Uani 1 1 d . . .
H4A H 0.9249 1.6334 0.8362 0.038 Uiso 1 1 calc R . .
C5 C 1.12921(17) 1.68157(15) 0.93017(10) 0.0252(3) Uani 1 1 d . . .
C6 C 1.12417(16) 1.54425(14) 0.91563(10) 0.0238(3) Uani 1 1 d . . .
C7 C 1.24901(17) 1.52928(16) 0.96713(11) 0.0287(3) Uani 1 1 d . . .
C8 C 1.37905(18) 1.64853(17) 1.03270(12) 0.0369(4) Uani 1 1 d . . .
H8A H 1.4620 1.6381 1.0659 0.044 Uiso 1 1 calc R . .
C9 C 1.38341(18) 1.77681(17) 1.04724(11) 0.0361(4) Uani 1 1 d . . .
H9A H 1.4687 1.8530 1.0916 0.043 Uiso 1 1 calc R . .
C10 C 1.26111(17) 1.79880(15) 0.99660(10) 0.0291(3) Uani 1 1 d . . .
C11 C 0.99620(16) 1.42381(15) 0.84652(10) 0.0245(3) Uani 1 1 d . . .
H11A H 0.9143 1.4348 0.8125 0.029 Uiso 1 1 calc R . .
C12 C 0.87180(16) 1.18197(14) 0.75953(10) 0.0231(3) Uani 1 1 d . . .
C13 C 0.74310(18) 1.18055(16) 0.70071(12) 0.0315(4) Uani 1 1 d . . .
H13A H 0.7298 1.2620 0.7075 0.038 Uiso 1 1 calc R . .
C14 C 0.63516(17) 1.05811(15) 0.63224(11) 0.0304(4) Uani 1 1 d . . .
H14A H 0.5492 1.0582 0.5937 0.037 Uiso 1 1 calc R . .
C15 C 0.65178(15) 0.93532(14) 0.61959(10) 0.0221(3) Uani 1 1 d . . .
C16 C 0.77952(17) 0.93654(15) 0.67857(11) 0.0293(3) Uani 1 1 d . . .
H16A H 0.7926 0.8550 0.6716 0.035 Uiso 1 1 calc R . .
C17 C 0.88757(17) 1.05855(15) 0.74774(11) 0.0285(3) Uani 1 1 d . . .
H17A H 0.9723 1.0578 0.7870 0.034 Uiso 1 1 calc R . .
C18 C 0.53623(15) 0.80103(14) 0.54642(10) 0.0208(3) Uani 1 1 d . . .
C19 C 0.57289(15) 0.76446(14) 0.45191(10) 0.0219(3) Uani 1 1 d . . .
C20 C 0.69505(16) 0.83956(15) 0.40176(11) 0.0271(3) Uani 1 1 d . . .
C21 C 0.81517(18) 0.99144(16) 0.43425(13) 0.0357(4) Uani 1 1 d . . .
H21A H 0.8894 1.0102 0.3885 0.054 Uiso 1 1 calc R . .
H21B H 0.8728 1.0119 0.5001 0.054 Uiso 1 1 calc R . .
H21C H 0.7600 1.0491 0.4348 0.054 Uiso 1 1 calc R . .
C22 C 0.67578(18) 0.74712(17) 0.31168(12) 0.0337(4) Uani 1 1 d . . .
H22A H 0.7397 0.7670 0.2632 0.040 Uiso 1 1 calc R . .
C23 C 0.54504(17) 0.61889(16) 0.30482(11) 0.0293(3) Uani 1 1 d . . .
C24 C 0.4805(2) 0.48697(17) 0.22273(12) 0.0391(4) Uani 1 1 d . . .
H24A H 0.4752 0.4111 0.2497 0.059 Uiso 1 1 calc R . .
H24B H 0.5500 0.4980 0.1740 0.059 Uiso 1 1 calc R . .
H24C H 0.3748 0.4668 0.1916 0.059 Uiso 1 1 calc R . .
C25 C 0.18991(17) 0.50724(16) 0.56371(11) 0.0293(3) Uani 1 1 d . . .
C26 C 0.06716(18) 0.35896(16) 0.52178(13) 0.0380(4) Uani 1 1 d . . .
H26A H 0.0251 0.3452 0.4533 0.057 Uiso 1 1 calc R . .
H26B H -0.0186 0.3390 0.5595 0.057 Uiso 1 1 calc R . .
H26C H 0.1160 0.2973 0.5255 0.057 Uiso 1 1 calc R . .
C27 C 0.21014(18) 0.59582(17) 0.65723(12) 0.0362(4) Uani 1 1 d . . .
H27A H 0.1454 0.5731 0.7049 0.043 Uiso 1 1 calc R . .
C28 C 0.34077(17) 0.72195(16) 0.66763(11) 0.0312(4) Uani 1 1 d . . .
C29 C 0.4008(2) 0.8452(2) 0.75742(13) 0.0507(5) Uani 1 1 d . . .
H29A H 0.3387 0.8200 0.8086 0.076 Uiso 1 1 calc R . .
H29B H 0.3903 0.9219 0.7392 0.076 Uiso 1 1 calc R . .
H29C H 0.5118 0.8725 0.7820 0.076 Uiso 1 1 calc R . .
C30 C 0.40228(16) 0.71035(14) 0.57673(10) 0.0230(3) Uani 1 1 d . . .
B1 B 0.32373(19) 0.51997(17) 0.40762(12) 0.0243(4) Uani 1 1 d . . .
N1 N 0.99198(14) 1.30087(12) 0.83049(9) 0.0265(3) Uani 1 1 d . . .
N2 N 0.48111(13) 0.62984(12) 0.38871(8) 0.0231(3) Uani 1 1 d . . .
N3 N 0.30403(13) 0.57603(11) 0.51432(8) 0.0228(3) Uani 1 1 d . . .
F1 F 0.32618(11) 0.39175(9) 0.39580(7) 0.0393(2) Uani 1 1 d . . .
F2 F 0.19482(9) 0.50448(9) 0.33946(6) 0.0348(2) Uani 1 1 d . . .
O1 O 1.25232(13) 1.40626(12) 0.95612(9) 0.0389(3) Uani 1 1 d . . .
H1B H 1.149(3) 1.336(2) 0.9081(18) 0.088(8) Uiso 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
C1 C2 1.356(2) . ?
C1 C10 1.411(2) . ?
C2 C3 1.405(2) . ?
C3 C4 1.362(2) . ?
C4 C5 1.407(2) . ?
C5 C10 1.4240(19) . ?
C5 C6 1.444(2) . ?
C6 C7 1.404(2) . ?
C6 C11 1.4384(19) . ?
C7 O1 1.3272(18) . ?
C7 C8 1.421(2) . ?
C8 C9 1.349(2) . ?
C9 C10 1.424(2) . ?
C11 N1 1.2913(18) . ?
C12 C17 1.387(2) . ?
C12 C13 1.393(2) . ?
C12 N1 1.4147(17) . ?
C13 C14 1.382(2) . ?
C14 C15 1.383(2) . ?
C15 C16 1.3876(19) . ?
C15 C18 1.4965(18) . ?
C16 C17 1.384(2) . ?
C18 C30 1.3885(19) . ?
C18 C19 1.3995(19) . ?
C19 N2 1.3997(17) . ?
C19 C20 1.422(2) . ?
C20 C22 1.379(2) . ?
C20 C21 1.504(2) . ?
C22 C23 1.396(2) . ?
C23 N2 1.3517(18) . ?
C23 C24 1.491(2) . ?
C25 N3 1.3473(18) . ?
C25 C27 1.394(2) . ?
C25 C26 1.491(2) . ?
C27 C28 1.372(2) . ?
C28 C30 1.427(2) . ?
C28 C29 1.498(2) . ?
C30 N3 1.4029(17) . ?
B1 F1 1.3788(18) . ?
B1 F2 1.4020(17) . ?
B1 N3 1.536(2) . ?
B1 N2 1.539(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
C2 C1 C10 121.57(14) . . ?
C1 C2 C3 119.03(16) . . ?
C4 C3 C2 120.93(16) . . ?
C3 C4 C5 121.71(14) . . ?
C4 C5 C10 117.24(14) . . ?
C4 C5 C6 123.68(13) . . ?
C10 C5 C6 119.05(13) . . ?
C7 C6 C11 119.69(13) . . ?
C7 C6 C5 119.41(13) . . ?
C11 C6 C5 120.86(13) . . ?
O1 C7 C6 122.31(13) . . ?
O1 C7 C8 117.59(13) . . ?
C6 C7 C8 120.10(14) . . ?
C9 C8 C7 120.68(14) . . ?
C8 C9 C10 121.82(14) . . ?
C1 C10 C9 121.53(14) . . ?
C1 C10 C5 119.51(14) . . ?
C9 C10 C5 118.94(14) . . ?
N1 C11 C6 121.76(13) . . ?
C17 C12 C13 118.50(13) . . ?
C17 C12 N1 116.14(12) . . ?
C13 C12 N1 125.35(13) . . ?
C14 C13 C12 119.96(14) . . ?
C13 C14 C15 121.60(13) . . ?
C14 C15 C16 118.44(13) . . ?
C14 C15 C18 122.74(12) . . ?
C16 C15 C18 118.81(12) . . ?
C17 C16 C15 120.30(14) . . ?
C16 C17 C12 121.20(13) . . ?
C30 C18 C19 121.48(12) . . ?
C30 C18 C15 119.18(12) . . ?
C19 C18 C15 119.12(12) . . ?
N2 C19 C18 119.96(12) . . ?
N2 C19 C20 107.71(12) . . ?
C18 C19 C20 132.32(13) . . ?
C22 C20 C19 106.10(13) . . ?
C22 C20 C21 125.45(14) . . ?
C19 C20 C21 128.31(14) . . ?
C20 C22 C23 109.15(13) . . ?
N2 C23 C22 108.55(13) . . ?
N2 C23 C24 122.75(14) . . ?
C22 C23 C24 128.69(14) . . ?
N3 C25 C27 108.96(13) . . ?
N3 C25 C26 123.28(14) . . ?
C27 C25 C26 127.75(14) . . ?
C28 C27 C25 109.14(14) . . ?
C27 C28 C30 106.19(13) . . ?
C27 C28 C29 125.32(15) . . ?
C30 C28 C29 128.49(14) . . ?
C18 C30 N3 120.25(12) . . ?
C18 C30 C28 132.16(13) . . ?
N3 C30 C28 107.51(12) . . ?
F1 B1 F2 108.82(12) . . ?
F1 B1 N3 111.02(12) . . ?
F2 B1 N3 109.32(12) . . ?
F1 B1 N2 111.30(12) . . ?
F2 B1 N2 109.01(12) . . ?
N3 B1 N2 107.34(11) . . ?
C11 N1 C12 122.93(12) . . ?
C23 N2 C19 108.45(12) . . ?
C23 N2 B1 126.19(12) . . ?
C19 N2 B1 125.05(12) . . ?
C25 N3 C30 108.20(12) . . ?
C25 N3 B1 126.62(12) . . ?
C30 N3 B1 125.17(11) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 1000810'
