# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_CF3_Imd
_database_code_depnum_ccdc_archive 'CCDC 1044387'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C58 H36 B2 F10 N5 O2'
_chemical_formula_sum            'C58 H36 B2 F10 N5 O2'
_chemical_formula_weight         1046.54

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'
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'
B B 0.0013 0.0007 '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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   31.603(4)
_cell_length_b                   8.6107(10)
_cell_length_c                   22.928(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 129.760(11)
_cell_angle_gamma                90.00
_cell_volume                     4796.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      30.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2140
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6439
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39509
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         30.56
_reflns_number_total             7309
_reflns_number_gt                6174
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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)+(0.0646P)²+3.5885P] 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         7309
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
F3 F 0.83675(4) 0.84595(16) 0.07939(5) 0.0529(3) Uani 1 1 d . . .
F4 F 0.79700(4) 1.04960(11) 0.07839(5) 0.0448(3) Uani 1 1 d . . .
F5 F 0.76338(4) 0.82579(12) 0.06492(4) 0.0377(2) Uani 1 1 d . . .
F2 F 1.04949(3) 0.78328(9) 0.65794(4) 0.02153(15) Uani 1 1 d . . .
F1 F 1.00983(3) 0.54464(8) 0.63500(4) 0.02104(15) Uani 1 1 d . . .
O1 O 1.05445(3) 0.59591(9) 0.58806(4) 0.01702(16) Uani 1 1 d . . .
N2 N 0.91401(4) 0.80739(11) 0.41269(5) 0.01357(17) Uani 1 1 d . . .
N1 N 0.96690(4) 0.72798(10) 0.53063(5) 0.01320(16) Uani 1 1 d . . .
N3 N 0.0000 0.0771(2) 0.7500 0.0464(5) Uani 1 2 d S . .
C7 C 0.87421(5) 0.65722(14) 0.64936(7) 0.0203(2) Uani 1 1 d . . .
H7 H 0.8657 0.6387 0.6808 0.024 Uiso 1 1 calc R . .
C6 C 0.84108(5) 0.59510(14) 0.57646(7) 0.0208(2) Uani 1 1 d . . .
H6 H 0.8104 0.5358 0.5592 0.025 Uiso 1 1 calc R . .
C5 C 0.85385(4) 0.62183(13) 0.52935(6) 0.0174(2) Uani 1 1 d . . .
H5 H 0.8316 0.5811 0.4805 0.021 Uiso 1 1 calc R . .
C4 C 0.90010(4) 0.70988(12) 0.55554(6) 0.01403(19) Uani 1 1 d . . .
C3 C 0.91375(4) 0.74055(12) 0.50603(6) 0.01336(18) Uani 1 1 d . . .
C2 C 0.88017(4) 0.78942(12) 0.43199(6) 0.01382(19) Uani 1 1 d . . .
C16 C 0.89361(4) 0.84016(12) 0.33706(6) 0.01344(18) Uani 1 1 d . . .
C21 C 0.86732(4) 0.98032(12) 0.30339(6) 0.01606(19) Uani 1 1 d . . .
H21 H 0.8668 1.0575 0.3313 0.019 Uiso 1 1 calc R . .
C20 C 0.84178(4) 1.00380(13) 0.22722(6) 0.0176(2) Uani 1 1 d . . .
H20 H 0.8236 1.0966 0.2035 0.021 Uiso 1 1 calc R . .
C19 C 0.84370(4) 0.88775(13) 0.18704(6) 0.0163(2) Uani 1 1 d . . .
C22 C 0.81106(5) 0.90404(15) 0.10313(7) 0.0224(2) Uani 1 1 d . . .
C17 C 0.89716(4) 0.72480(12) 0.29772(6) 0.0161(2) Uani 1 1 d . . .
H17 H 0.9158 0.6326 0.3217 0.019 Uiso 1 1 calc R . .
C18 C 0.87233(5) 0.74997(13) 0.22223(6) 0.0173(2) Uani 1 1 d . . .
H18 H 0.8748 0.6753 0.1952 0.021 Uiso 1 1 calc R . .
C11 C 1.05897(4) 0.67477(12) 0.54136(6) 0.01424(19) Uani 1 1 d . . .
C10 C 1.01585(4) 0.76952(12) 0.48254(6) 0.01394(19) Uani 1 1 d . . .
C15 C 1.02289(4) 0.85386(13) 0.43699(6) 0.0162(2) Uani 1 1 d . . .
H15 H 0.9952 0.9197 0.3995 0.019 Uiso 1 1 calc R . .
C14 C 1.07108(5) 0.83931(13) 0.44773(6) 0.0185(2) Uani 1 1 d . . .
H14 H 1.0759 0.8959 0.4178 0.022 Uiso 1 1 calc R . .
C13 C 1.11252(5) 0.73921(13) 0.50377(7) 0.0182(2) Uani 1 1 d . . .
H13 H 1.1443 0.7270 0.5097 0.022 Uiso 1 1 calc R . .
C12 C 1.10682(4) 0.65798(13) 0.55052(6) 0.0166(2) Uani 1 1 d . . .
H12 H 1.1348 0.5925 0.5879 0.020 Uiso 1 1 calc R . .
C1 C 0.96620(4) 0.77044(12) 0.47392(6) 0.01327(18) Uani 1 1 d . . .
C8 C 0.91986(5) 0.74661(13) 0.67543(6) 0.0183(2) Uani 1 1 d . . .
H8 H 0.9417 0.7888 0.7240 0.022 Uiso 1 1 calc R . .
C9 C 0.93284(4) 0.77274(13) 0.62864(6) 0.0163(2) Uani 1 1 d . . .
H9 H 0.9635 0.8323 0.6461 0.020 Uiso 1 1 calc R . .
C23 C 0.82067(4) 0.82127(12) 0.37814(6) 0.01445(19) Uani 1 1 d . . .
C24 C 0.78699(4) 0.75206(13) 0.30630(6) 0.0175(2) Uani 1 1 d . . .
H24 H 0.8021 0.6827 0.2930 0.021 Uiso 1 1 calc R . .
C25 C 0.73105(5) 0.78624(14) 0.25464(7) 0.0209(2) Uani 1 1 d . . .
H25 H 0.7090 0.7407 0.2068 0.025 Uiso 1 1 calc R . .
C26 C 0.70814(5) 0.88829(15) 0.27451(7) 0.0228(2) Uani 1 1 d . . .
H26 H 0.6708 0.9119 0.2399 0.027 Uiso 1 1 calc R . .
C27 C 0.74116(5) 0.95522(14) 0.34632(7) 0.0226(2) Uani 1 1 d . . .
H27 H 0.7257 1.0224 0.3599 0.027 Uiso 1 1 calc R . .
C28 C 0.79729(5) 0.92236(13) 0.39817(7) 0.0184(2) Uani 1 1 d . . .
H28 H 0.8191 0.9677 0.4461 0.022 Uiso 1 1 calc R . .
C29 C 0.0000 0.2092(2) 0.7500 0.0287(4) Uani 1 2 d S . .
C30 C 0.0000 0.3780(2) 0.7500 0.0482(7) Uani 1 2 d S . .
B1 B 1.02185(5) 0.66144(14) 0.60673(7) 0.0156(2) 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
F3 C22 1.3308(15) . ?
F4 C22 1.3295(15) . ?
F5 C22 1.3428(15) . ?
F2 B1 1.3894(14) . ?
F1 B1 1.3751(13) . ?
O1 C11 1.3503(12) . ?
O1 B1 1.4585(14) . ?
N2 C1 1.3531(13) . ?
N2 C2 1.4029(13) . ?
N2 C16 1.4397(13) . ?
N1 C1 1.3372(13) . ?
N1 C3 1.3927(13) . ?
N1 B1 1.5851(15) . ?
N3 C29 1.137(3) . ?
C7 C8 1.3885(16) . ?
C7 C6 1.3919(17) . ?
C7 H7 0.9300 . ?
C6 C5 1.3929(15) . ?
C6 H6 0.9300 . ?
C5 C4 1.3962(15) . ?
C5 H5 0.9300 . ?
C4 C9 1.3980(15) . ?
C4 C3 1.4733(14) . ?
C3 C2 1.3715(14) . ?
C2 C23 1.4718(15) . ?
C16 C21 1.3865(14) . ?
C16 C17 1.3934(14) . ?
C21 C20 1.3925(15) . ?
C21 H21 0.9300 . ?
C20 C19 1.3865(15) . ?
C20 H20 0.9300 . ?
C19 C18 1.3941(16) . ?
C19 C22 1.4988(16) . ?
C17 C18 1.3862(15) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C11 C12 1.3948(14) . ?
C11 C10 1.4109(14) . ?
C10 C15 1.4018(14) . ?
C10 C1 1.4507(14) . ?
C15 C14 1.3842(15) . ?
C15 H15 0.9300 . ?
C14 C13 1.3987(16) . ?
C14 H14 0.9300 . ?
C13 C12 1.3849(15) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C8 C9 1.3902(15) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C23 C28 1.3958(15) . ?
C23 C24 1.3996(15) . ?
C24 C25 1.3916(16) . ?
C24 H24 0.9300 . ?
C25 C26 1.3877(18) . ?
C25 H25 0.9300 . ?
C26 C27 1.3908(18) . ?
C26 H26 0.9300 . ?
C27 C28 1.3938(16) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.453(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
C11 O1 B1 119.40(8) . . ?
C1 N2 C2 108.43(9) . . ?
C1 N2 C16 127.25(9) . . ?
C2 N2 C16 123.86(9) . . ?
C1 N1 C3 108.62(9) . . ?
C1 N1 B1 119.62(9) . . ?
C3 N1 B1 131.49(9) . . ?
C8 C7 C6 120.43(10) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C6 C5 119.95(11) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C5 C4 119.93(10) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 C9 119.63(10) . . ?
C5 C4 C3 120.52(9) . . ?
C9 C4 C3 119.82(9) . . ?
C2 C3 N1 107.64(9) . . ?
C2 C3 C4 129.25(9) . . ?
N1 C3 C4 123.07(9) . . ?
C3 C2 N2 106.37(9) . . ?
C3 C2 C23 131.11(9) . . ?
N2 C2 C23 122.52(9) . . ?
C21 C16 C17 121.85(10) . . ?
C21 C16 N2 119.24(9) . . ?
C17 C16 N2 118.72(9) . . ?
C16 C21 C20 119.01(10) . . ?
C16 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C19 C20 C21 119.48(10) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C19 C18 121.12(10) . . ?
C20 C19 C22 119.92(10) . . ?
C18 C19 C22 118.79(10) . . ?
F4 C22 F3 107.74(11) . . ?
F4 C22 F5 105.39(11) . . ?
F3 C22 F5 105.56(11) . . ?
F4 C22 C19 113.80(10) . . ?
F3 C22 C19 112.99(10) . . ?
F5 C22 C19 110.76(10) . . ?
C18 C17 C16 118.76(10) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C19 119.69(10) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
O1 C11 C12 118.87(9) . . ?
O1 C11 C10 121.43(9) . . ?
C12 C11 C10 119.68(9) . . ?
C15 C10 C11 119.69(9) . . ?
C15 C10 C1 124.68(9) . . ?
C11 C10 C1 115.64(9) . . ?
C14 C15 C10 120.10(10) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C15 C14 C13 119.76(10) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C12 C13 C14 120.88(10) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C12 C11 119.76(10) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N1 C1 N2 108.92(9) . . ?
N1 C1 C10 121.48(9) . . ?
N2 C1 C10 129.59(9) . . ?
C7 C8 C9 119.71(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 120.33(10) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C28 C23 C24 119.26(10) . . ?
C28 C23 C2 120.09(10) . . ?
C24 C23 C2 120.65(10) . . ?
C25 C24 C23 120.50(11) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.00(11) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 119.81(10) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 120.50(11) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C23 119.91(11) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
N3 C29 C30 180.000(3) . . ?
F1 B1 F2 111.58(9) . . ?
F1 B1 O1 108.39(9) . . ?
F2 B1 O1 111.09(9) . . ?
F1 B1 N1 110.16(9) . . ?
F2 B1 N1 108.13(9) . . ?
O1 B1 N1 107.40(8) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.56
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_H_Imd
_database_code_depnum_ccdc_archive 'CCDC 1044388'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H19 B F2 N2 O'
_chemical_formula_sum            'C27 H19 B F2 N2 O'
_chemical_formula_weight         436.25

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'
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'
B B 0.0013 0.0007 '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                   10.2847(4)
_cell_length_b                   10.8082(4)
_cell_length_c                   10.9755(4)
_cell_angle_alpha                85.101(3)
_cell_angle_beta                 75.591(3)
_cell_angle_gamma                67.342(2)
_cell_volume                     1090.38(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3217
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      24.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6594
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16890
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -12
_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       14
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         28.30
_reflns_number_total             5404
_reflns_number_gt                3086
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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)+(0.0527P)²+0.1335P] 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       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5404
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
F1 F -0.06041(12) 1.28597(9) 0.68942(11) 0.0652(3) Uani 1 1 d . . .
F2 F -0.11304(12) 1.26832(11) 0.90201(11) 0.0764(4) Uani 1 1 d . . .
O1 O -0.23971(13) 1.20574(12) 0.79132(13) 0.0596(4) Uani 1 1 d . . .
N2 N 0.10622(15) 0.85324(12) 0.72454(13) 0.0445(4) Uani 1 1 d . . .
N1 N 0.01604(14) 1.06541(12) 0.77535(13) 0.0431(3) Uani 1 1 d . . .
C19 C 0.1339(4) 0.4865(2) 0.6035(3) 0.0947(9) Uani 1 1 d . . .
H19 H 0.1379 0.4064 0.5748 0.114 Uiso 1 1 calc R . .
C18 C 0.0338(3) 0.5466(2) 0.7093(3) 0.0847(8) Uani 1 1 d . . .
H18 H -0.0292 0.5066 0.7534 0.102 Uiso 1 1 calc R . .
C17 C 0.0258(2) 0.66668(18) 0.7512(2) 0.0669(6) Uani 1 1 d . . .
H17 H -0.0414 0.7077 0.8242 0.080 Uiso 1 1 calc R . .
C16 C 0.11859(19) 0.72466(15) 0.68333(17) 0.0472(4) Uani 1 1 d . . .
C2 C 0.20366(18) 0.87456(15) 0.78037(15) 0.0430(4) Uani 1 1 d . . .
C3 C 0.14621(18) 1.00761(15) 0.81250(15) 0.0430(4) Uani 1 1 d . . .
C4 C 0.20596(18) 1.08338(15) 0.87262(16) 0.0447(4) Uani 1 1 d . . .
C5 C 0.2643(2) 1.03128(18) 0.97579(17) 0.0541(5) Uani 1 1 d . . .
H5 H 0.2634 0.9493 1.0084 0.065 Uiso 1 1 calc R . .
C6 C 0.3239(2) 1.1010(2) 1.03012(18) 0.0632(5) Uani 1 1 d . . .
H6 H 0.3629 1.0656 1.0991 0.076 Uiso 1 1 calc R . .
C7 C 0.3255(2) 1.2227(2) 0.9823(2) 0.0674(6) Uani 1 1 d . . .
H7 H 0.3660 1.2691 1.0189 0.081 Uiso 1 1 calc R . .
C25 C -0.3845(2) 1.0742(2) 0.5870(2) 0.0725(6) Uani 1 1 d . . .
H25 H -0.4704 1.0968 0.5614 0.087 Uiso 1 1 calc R . .
C24 C -0.3751(2) 1.1550(2) 0.6714(2) 0.0654(6) Uani 1 1 d . . .
H24 H -0.4546 1.2321 0.7027 0.078 Uiso 1 1 calc R . .
C23 C -0.2475(2) 1.12204(18) 0.71051(18) 0.0524(5) Uani 1 1 d . . .
C1 C -0.00529(18) 0.97109(15) 0.72060(16) 0.0434(4) Uani 1 1 d . . .
C20 C 0.2291(3) 0.5430(2) 0.5387(2) 0.0945(9) Uani 1 1 d . . .
H20 H 0.2988 0.5000 0.4677 0.113 Uiso 1 1 calc R . .
C21 C 0.2215(3) 0.66417(19) 0.57895(18) 0.0661(6) Uani 1 1 d . . .
H21 H 0.2855 0.7034 0.5355 0.079 Uiso 1 1 calc R . .
C10 C 0.34470(19) 0.76946(15) 0.78693(16) 0.0438(4) Uani 1 1 d . . .
C11 C 0.3564(2) 0.64523(16) 0.84032(16) 0.0517(5) Uani 1 1 d . . .
H11 H 0.2734 0.6277 0.8764 0.062 Uiso 1 1 calc R . .
C12 C 0.4915(2) 0.54816(17) 0.83953(19) 0.0618(5) Uani 1 1 d . . .
H12 H 0.4990 0.4649 0.8745 0.074 Uiso 1 1 calc R . .
C13 C 0.6145(2) 0.57289(19) 0.78800(19) 0.0644(6) Uani 1 1 d . . .
H13 H 0.7049 0.5065 0.7878 0.077 Uiso 1 1 calc R . .
C14 C 0.6046(2) 0.69606(19) 0.73638(18) 0.0588(5) Uani 1 1 d . . .
H14 H 0.6882 0.7133 0.7022 0.071 Uiso 1 1 calc R . .
C15 C 0.47052(19) 0.79351(17) 0.73567(16) 0.0501(4) Uani 1 1 d . . .
H15 H 0.4641 0.8764 0.7004 0.060 Uiso 1 1 calc R . .
C8 C 0.2678(2) 1.27522(19) 0.8812(2) 0.0642(5) Uani 1 1 d . . .
H8 H 0.2682 1.3578 0.8497 0.077 Uiso 1 1 calc R . .
C9 C 0.2087(2) 1.20614(17) 0.82564(18) 0.0551(5) Uani 1 1 d . . .
H9 H 0.1706 1.2420 0.7563 0.066 Uiso 1 1 calc R . .
C22 C -0.13082(19) 1.00201(16) 0.66898(17) 0.0469(4) Uani 1 1 d . . .
C27 C -0.1420(2) 0.92332(19) 0.58043(18) 0.0570(5) Uani 1 1 d . . .
H27 H -0.0638 0.8455 0.5488 0.068 Uiso 1 1 calc R . .
C26 C -0.2676(2) 0.9601(2) 0.5398(2) 0.0693(6) Uani 1 1 d . . .
H26 H -0.2736 0.9076 0.4802 0.083 Uiso 1 1 calc R . .
B1 B -0.1015(2) 1.21337(19) 0.7912(2) 0.0513(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
F1 B1 1.383(2) . ?
F2 B1 1.357(2) . ?
O1 C23 1.356(2) . ?
O1 B1 1.455(3) . ?
N2 C1 1.3526(19) . ?
N2 C2 1.393(2) . ?
N2 C16 1.4472(19) . ?
N1 C1 1.338(2) . ?
N1 C3 1.390(2) . ?
N1 B1 1.582(2) . ?
C19 C18 1.360(4) . ?
C19 C20 1.369(4) . ?
C19 H19 0.9300 . ?
C18 C17 1.380(3) . ?
C18 H18 0.9300 . ?
C17 C16 1.373(3) . ?
C17 H17 0.9300 . ?
C16 C21 1.361(3) . ?
C2 C3 1.367(2) . ?
C2 C10 1.472(2) . ?
C3 C4 1.472(2) . ?
C4 C5 1.389(2) . ?
C4 C9 1.390(2) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(3) . ?
C7 H7 0.9300 . ?
C25 C24 1.370(3) . ?
C25 C26 1.376(3) . ?
C25 H25 0.9300 . ?
C24 C23 1.389(3) . ?
C24 H24 0.9300 . ?
C23 C22 1.400(2) . ?
C1 C22 1.449(2) . ?
C20 C21 1.385(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C10 C15 1.389(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C22 C27 1.398(2) . ?
C27 C26 1.374(3) . ?
C27 H27 0.9300 . ?
C26 H26 0.9300 . ?

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
C23 O1 B1 120.63(15) . . ?
C1 N2 C2 108.96(12) . . ?
C1 N2 C16 125.49(14) . . ?
C2 N2 C16 125.48(13) . . ?
C1 N1 C3 108.84(13) . . ?
C1 N1 B1 119.92(14) . . ?
C3 N1 B1 131.22(14) . . ?
C18 C19 C20 120.6(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C16 C17 C18 118.9(2) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C21 C16 C17 121.68(17) . . ?
C21 C16 N2 119.46(16) . . ?
C17 C16 N2 118.87(17) . . ?
C3 C2 N2 106.41(14) . . ?
C3 C2 C10 130.66(16) . . ?
N2 C2 C10 122.67(13) . . ?
C2 C3 N1 107.55(14) . . ?
C2 C3 C4 128.91(15) . . ?
N1 C3 C4 123.53(14) . . ?
C5 C4 C9 118.77(16) . . ?
C5 C4 C3 120.27(15) . . ?
C9 C4 C3 120.94(15) . . ?
C6 C5 C4 120.19(17) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.21(19) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 120.10(19) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C24 C25 C26 120.4(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C24 C23 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
O1 C23 C24 119.04(18) . . ?
O1 C23 C22 121.12(16) . . ?
C24 C23 C22 119.82(19) . . ?
N1 C1 N2 108.22(14) . . ?
N1 C1 C22 121.67(14) . . ?
N2 C1 C22 130.11(15) . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 118.7(2) . . ?
C16 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C15 C10 C11 118.77(16) . . ?
C15 C10 C2 119.15(14) . . ?
C11 C10 C2 122.06(16) . . ?
C12 C11 C10 119.81(18) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.79(18) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.09(18) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 120.80(17) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C7 C8 C9 120.23(19) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 120.50(17) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C27 C22 C23 118.59(17) . . ?
C27 C22 C1 125.12(16) . . ?
C23 C22 C1 116.27(16) . . ?
C26 C27 C22 120.5(2) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C27 C26 C25 120.2(2) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
F2 B1 F1 111.76(16) . . ?
F2 B1 O1 108.89(17) . . ?
F1 B1 O1 110.55(16) . . ?
F2 B1 N1 110.71(15) . . ?
F1 B1 N1 107.49(15) . . ?
O1 B1 N1 107.35(14) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.035
