# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20151111a_0m
_database_code_depnum_ccdc_archive 'CCDC 1455216'
_audit_update_record             
;
2016-02-23 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H18 B F2 N3 O3'
_chemical_formula_weight         553.31

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   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.4915(12)
_cell_length_b                   14.5392(16)
_cell_length_c                   15.7532(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2632.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2295
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8376
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.20
_reflns_number_total             4687
_reflns_number_gt                3513
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0415P)²+0.1455P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(9)
_refine_ls_number_reflns         4687
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
C11 C 0.4709(2) 0.61501(17) 0.37412(15) 0.0452(6) Uani 1 1 d . . .
C7 C 0.4745(3) 0.83480(18) 0.56489(18) 0.0654(7) Uani 1 1 d . . .
H7 H 0.4200 0.8353 0.6085 0.078 Uiso 1 1 calc R . .
C12 C 0.4643(2) 0.54483(15) 0.43791(15) 0.0454(6) Uani 1 1 d . . .
C3 C 0.7198(2) 0.8345(2) 0.36584(18) 0.0641(8) Uani 1 1 d . . .
H3 H 0.7760 0.8804 0.3632 0.077 Uiso 1 1 calc R . .
C9 C 0.5561(2) 0.76266(16) 0.43935(15) 0.0462(6) Uani 1 1 d . . .
C8 C 0.4747(2) 0.76509(18) 0.50614(15) 0.0533(6) Uani 1 1 d . . .
H8 H 0.4198 0.7183 0.5105 0.064 Uiso 1 1 calc R . .
C10 C 0.5566(2) 0.69190(16) 0.37610(14) 0.0442(6) Uani 1 1 d . . .
C17 C 0.3835(2) 0.47137(15) 0.42612(16) 0.0475(6) Uani 1 1 d . . .
C2 C 0.7180(2) 0.7685(2) 0.30441(17) 0.0570(7) Uani 1 1 d . . .
H2 H 0.7703 0.7703 0.2594 0.068 Uiso 1 1 calc R . .
C4 C 0.6390(2) 0.83521(17) 0.43331(16) 0.0556(7) Uani 1 1 d . . .
C19 C 0.3215(2) 0.53576(19) 0.29241(16) 0.0556(7) Uani 1 1 d . . .
H19 H 0.2749 0.5336 0.2442 0.067 Uiso 1 1 calc R . .
C16 C 0.3757(3) 0.40326(18) 0.4897(2) 0.0613(8) Uani 1 1 d . . .
H16 H 0.3251 0.3539 0.4825 0.074 Uiso 1 1 calc R . .
C1 C 0.6355(2) 0.69796(17) 0.31073(15) 0.0462(6) Uani 1 1 d . . .
C5 C 0.6362(3) 0.9064(2) 0.4949(2) 0.0753(9) Uani 1 1 d . . .
H5 H 0.6893 0.9546 0.4916 0.090 Uiso 1 1 calc R . .
C14 C 0.5235(3) 0.47888(17) 0.57143(18) 0.0629(7) Uani 1 1 d . . .
H14 H 0.5699 0.4806 0.6198 0.075 Uiso 1 1 calc R . .
C18 C 0.3145(2) 0.46837(19) 0.35168(17) 0.0591(7) Uani 1 1 d . . .
H18 H 0.2637 0.4194 0.3433 0.071 Uiso 1 1 calc R . .
C15 C 0.4413(3) 0.40892(18) 0.5614(2) 0.0649(8) Uani 1 1 d . . .
H15 H 0.4314 0.3656 0.6042 0.078 Uiso 1 1 calc R . .
C20 C 0.3993(2) 0.60857(17) 0.30447(15) 0.0450(6) Uani 1 1 d . . .
C6 C 0.5568(3) 0.9050(2) 0.5586(2) 0.0819(10) Uani 1 1 d . . .
H6 H 0.5573 0.9517 0.5988 0.098 Uiso 1 1 calc R . .
C13 C 0.5358(2) 0.54473(17) 0.51031(16) 0.0543(7) Uani 1 1 d . . .
H13 H 0.5921 0.5901 0.5167 0.065 Uiso 1 1 calc R . .
C21 C 0.4638(2) 0.66710(15) 0.17173(14) 0.0433(5) Uani 1 1 d . . .
C25 C 0.6446(2) 0.63044(15) 0.09956(14) 0.0442(6) Uani 1 1 d . . .
H25 H 0.7221 0.6120 0.1008 0.053 Uiso 1 1 calc R . .
C22 C 0.40871(19) 0.68480(15) 0.09581(14) 0.0440(5) Uani 1 1 d . . .
H22 H 0.3312 0.7031 0.0944 0.053 Uiso 1 1 calc R . .
C23 C 0.4719(2) 0.67469(15) 0.02174(14) 0.0409(5) Uani 1 1 d . . .
C24 C 0.5869(2) 0.64601(15) 0.02311(14) 0.0407(5) Uani 1 1 d . . .
C26 C 0.5821(2) 0.64360(15) 0.17345(14) 0.0432(6) Uani 1 1 d . . .
O1 O 0.63961(13) 0.62738(11) 0.24995(10) 0.0499(4) Uani 1 1 d . . .
O2 O 0.39918(13) 0.68044(11) 0.24500(10) 0.0487(4) Uani 1 1 d . . .
B1 B 0.5434(3) 0.6748(2) -0.21258(19) 0.0584(8) Uani 1 1 d . . .
F2 F 0.47170(14) 0.61278(16) -0.25117(12) 0.1016(7) Uani 1 1 d . . .
F1 F 0.52356(17) 0.76170(13) -0.24151(11) 0.0938(6) Uani 1 1 d . . .
N2 N 0.53672(16) 0.66909(13) -0.11669(11) 0.0425(5) Uani 1 1 d . . .
N1 N 0.67431(17) 0.64702(13) -0.23469(12) 0.0486(5) Uani 1 1 d . . .
O3 O 0.34682(14) 0.71861(12) -0.09554(10) 0.0547(4) Uani 1 1 d . . .
C28 C 0.6270(2) 0.64211(15) -0.06506(15) 0.0427(5) Uani 1 1 d . . .
C27 C 0.4383(2) 0.69120(15) -0.06711(15) 0.0433(6) Uani 1 1 d . . .
N3 N 0.72958(17) 0.61738(14) -0.09016(12) 0.0492(5) Uani 1 1 d . . .
C31 C 0.8940(3) 0.5992(2) -0.2872(2) 0.0661(8) Uani 1 1 d . . .
H31 H 0.9688 0.5839 -0.3048 0.079 Uiso 1 1 calc R . .
C29 C 0.7544(2) 0.62027(16) -0.17652(16) 0.0476(6) Uani 1 1 d . . .
C30 C 0.8652(2) 0.59551(18) -0.20312(18) 0.0599(7) Uani 1 1 d . . .
H30 H 0.9201 0.5763 -0.1635 0.072 Uiso 1 1 calc R . .
C32 C 0.8120(3) 0.6256(2) -0.34539(18) 0.0686(8) Uani 1 1 d . . .
H32 H 0.8296 0.6265 -0.4030 0.082 Uiso 1 1 calc R . .
C33 C 0.7043(2) 0.6506(2) -0.31760(16) 0.0608(7) Uani 1 1 d . . .
H33 H 0.6496 0.6707 -0.3569 0.073 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 C20 1.374(3) . ?
C11 C12 1.434(3) . ?
C11 C10 1.490(3) . ?
C7 C8 1.373(4) . ?
C7 C6 1.395(4) . ?
C12 C13 1.405(4) . ?
C12 C17 1.427(3) . ?
C3 C2 1.363(4) . ?
C3 C4 1.411(4) . ?
C9 C8 1.408(4) . ?
C9 C4 1.425(3) . ?
C9 C10 1.432(3) . ?
C10 C1 1.375(3) . ?
C17 C16 1.411(4) . ?
C17 C18 1.416(4) . ?
C2 C1 1.401(3) . ?
C4 C5 1.420(4) . ?
C19 C18 1.356(4) . ?
C19 C20 1.399(3) . ?
C16 C15 1.361(4) . ?
C1 O1 1.404(3) . ?
C5 C6 1.355(5) . ?
C14 C13 1.365(4) . ?
C14 C15 1.397(4) . ?
C20 O2 1.403(3) . ?
C21 C22 1.378(3) . ?
C21 O2 1.386(3) . ?
C21 C26 1.401(3) . ?
C25 C26 1.381(3) . ?
C25 C24 1.393(3) . ?
C22 C23 1.382(3) . ?
C23 C24 1.387(3) . ?
C23 C27 1.471(3) . ?
C24 C28 1.464(3) . ?
C26 O1 1.395(3) . ?
B1 F1 1.363(4) . ?
B1 F2 1.364(4) . ?
B1 N2 1.515(3) . ?
B1 N1 1.597(4) . ?
N2 C28 1.375(3) . ?
N2 C27 1.411(3) . ?
N1 C33 1.352(3) . ?
N1 C29 1.356(3) . ?
O3 C27 1.211(3) . ?
C28 N3 1.295(3) . ?
N3 C29 1.391(3) . ?
C31 C30 1.366(4) . ?
C31 C32 1.369(4) . ?
C29 C30 1.388(3) . ?
C32 C33 1.362(4) . ?

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
C20 C11 C12 118.7(2) . . ?
C20 C11 C10 117.6(2) . . ?
C12 C11 C10 123.6(2) . . ?
C8 C7 C6 119.4(3) . . ?
C13 C12 C17 119.0(2) . . ?
C13 C12 C11 122.6(2) . . ?
C17 C12 C11 118.4(2) . . ?
C2 C3 C4 122.0(2) . . ?
C8 C9 C4 118.4(2) . . ?
C8 C9 C10 122.7(2) . . ?
C4 C9 C10 118.9(2) . . ?
C7 C8 C9 121.6(3) . . ?
C1 C10 C9 118.5(2) . . ?
C1 C10 C11 117.9(2) . . ?
C9 C10 C11 123.4(2) . . ?
C16 C17 C18 122.0(2) . . ?
C16 C17 C12 118.3(2) . . ?
C18 C17 C12 119.7(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C4 C5 122.4(3) . . ?
C3 C4 C9 119.0(2) . . ?
C5 C4 C9 118.6(3) . . ?
C18 C19 C20 119.4(3) . . ?
C15 C16 C17 120.7(3) . . ?
C10 C1 C2 123.1(2) . . ?
C10 C1 O1 119.1(2) . . ?
C2 C1 O1 117.6(2) . . ?
C6 C5 C4 120.6(3) . . ?
C13 C14 C15 120.0(3) . . ?
C19 C18 C17 121.0(2) . . ?
C16 C15 C14 120.9(3) . . ?
C11 C20 C19 122.9(2) . . ?
C11 C20 O2 118.9(2) . . ?
C19 C20 O2 118.2(2) . . ?
C5 C6 C7 121.4(3) . . ?
C14 C13 C12 120.9(3) . . ?
C22 C21 O2 116.75(19) . . ?
C22 C21 C26 120.6(2) . . ?
O2 C21 C26 122.5(2) . . ?
C26 C25 C24 117.3(2) . . ?
C21 C22 C23 118.1(2) . . ?
C22 C23 C24 121.3(2) . . ?
C22 C23 C27 130.4(2) . . ?
C24 C23 C27 108.3(2) . . ?
C23 C24 C25 121.1(2) . . ?
C23 C24 C28 107.25(19) . . ?
C25 C24 C28 131.6(2) . . ?
C25 C26 O1 117.25(19) . . ?
C25 C26 C21 121.5(2) . . ?
O1 C26 C21 121.2(2) . . ?
C26 O1 C1 116.70(17) . . ?
C21 O2 C20 116.80(17) . . ?
F1 B1 F2 111.3(3) . . ?
F1 B1 N2 112.1(2) . . ?
F2 B1 N2 112.2(3) . . ?
F1 B1 N1 108.6(3) . . ?
F2 B1 N1 107.8(2) . . ?
N2 B1 N1 104.6(2) . . ?
C28 N2 C27 109.98(18) . . ?
C28 N2 B1 124.6(2) . . ?
C27 N2 B1 125.4(2) . . ?
C33 N1 C29 119.4(2) . . ?
C33 N1 B1 116.2(2) . . ?
C29 N1 B1 124.4(2) . . ?
N3 C28 N2 125.8(2) . . ?
N3 C28 C24 125.9(2) . . ?
N2 C28 C24 108.25(19) . . ?
O3 C27 N2 124.5(2) . . ?
O3 C27 C23 129.3(2) . . ?
N2 C27 C23 106.24(19) . . ?
C28 N3 C29 118.5(2) . . ?
C30 C31 C32 119.6(3) . . ?
N1 C29 C30 119.6(2) . . ?
N1 C29 N3 122.0(2) . . ?
C30 C29 N3 118.4(2) . . ?
C31 C30 C29 120.3(3) . . ?
C33 C32 C31 119.0(3) . . ?
N1 C33 C32 122.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.031
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20151112a_0m
_database_code_depnum_ccdc_archive 'CCDC 1455217'
_audit_update_record             
;
2016-02-23 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H18 B F2 N3 O3'
_chemical_formula_weight         553.31

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   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.4844(15)
_cell_length_b                   14.5457(16)
_cell_length_c                   15.7575(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2632.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2294
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8309
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.19
_reflns_number_total             4545
_reflns_number_gt                3285
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0369P)²+0.5201P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.2(11)
_refine_ls_number_reflns         4545
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C21 C -0.0359(2) 0.16750(19) 0.32801(15) 0.0414(6) Uani 1 1 d . . .
C25 C 0.1453(3) 0.13069(19) 0.40041(16) 0.0448(7) Uani 1 1 d . . .
H25 H 0.2230 0.1127 0.3992 0.054 Uiso 1 1 calc R . .
C26 C 0.0821(3) 0.14363(19) 0.32628(16) 0.0447(7) Uani 1 1 d . . .
C10 C 0.0565(3) 0.19157(19) 0.12403(16) 0.0440(7) Uani 1 1 d . . .
C9 C 0.0565(3) 0.2627(2) 0.06102(17) 0.0490(8) Uani 1 1 d . . .
C12 C -0.0355(3) 0.04512(19) 0.06235(17) 0.0451(7) Uani 1 1 d . . .
C11 C -0.0289(3) 0.1152(2) 0.12599(16) 0.0443(7) Uani 1 1 d . . .
C24 C 0.0870(3) 0.14589(18) 0.47669(16) 0.0404(7) Uani 1 1 d . . .
C23 C -0.0275(3) 0.17482(19) 0.47782(16) 0.0427(7) Uani 1 1 d . . .
C17 C -0.1158(3) -0.02846(19) 0.07371(18) 0.0483(8) Uani 1 1 d . . .
C22 C -0.0916(3) 0.18466(19) 0.40428(16) 0.0461(7) Uani 1 1 d . . .
H22 H -0.1695 0.2022 0.4059 0.055 Uiso 1 1 calc R . .
C7 C -0.0259(3) 0.3342(2) -0.0644(2) 0.0660(9) Uani 1 1 d . . .
H7 H -0.0801 0.3345 -0.1082 0.079 Uiso 1 1 calc R . .
C3 C 0.2197(3) 0.3352(2) 0.1345(2) 0.0638(9) Uani 1 1 d . . .
H3 H 0.2746 0.3820 0.1377 0.077 Uiso 1 1 calc R . .
C1 C 0.1346(3) 0.1982(2) 0.18912(17) 0.0464(7) Uani 1 1 d . . .
C19 C -0.1784(3) 0.0359(2) 0.20779(19) 0.0555(8) Uani 1 1 d . . .
H19 H -0.2250 0.0339 0.2560 0.067 Uiso 1 1 calc R . .
C4 C 0.1389(3) 0.3348(2) 0.06657(19) 0.0566(8) Uani 1 1 d . . .
C20 C -0.1005(3) 0.1085(2) 0.19526(17) 0.0444(7) Uani 1 1 d . . .
C15 C -0.0582(4) -0.0913(2) -0.0608(2) 0.0654(10) Uani 1 1 d . . .
H15 H -0.0673 -0.1353 -0.1031 0.078 Uiso 1 1 calc R . .
C8 C -0.0267(3) 0.2653(2) -0.00667(17) 0.0530(8) Uani 1 1 d . . .
H8 H -0.0822 0.2189 -0.0110 0.064 Uiso 1 1 calc R . .
C14 C 0.0238(3) -0.0209(2) -0.0715(2) 0.0625(9) Uani 1 1 d . . .
H14 H 0.0698 -0.0189 -0.1200 0.075 Uiso 1 1 calc R . .
C6 C 0.0559(4) 0.4049(3) -0.0584(2) 0.0795(12) Uani 1 1 d . . .
H6 H 0.0549 0.4523 -0.0980 0.095 Uiso 1 1 calc R . .
C16 C -0.1243(3) -0.0964(2) 0.0098(2) 0.0608(9) Uani 1 1 d . . .
H16 H -0.1759 -0.1451 0.0166 0.073 Uiso 1 1 calc R . .
C2 C 0.2188(3) 0.2687(2) 0.19507(19) 0.0605(9) Uani 1 1 d . . .
H2 H 0.2722 0.2697 0.2394 0.073 Uiso 1 1 calc R . .
C18 C -0.1850(3) -0.0316(2) 0.14843(19) 0.0564(9) Uani 1 1 d . . .
H18 H -0.2356 -0.0807 0.1568 0.068 Uiso 1 1 calc R . .
C13 C 0.0357(3) 0.0445(2) -0.01034(18) 0.0540(8) Uani 1 1 d . . .
H13 H 0.0921 0.0899 -0.0167 0.065 Uiso 1 1 calc R . .
C5 C 0.1379(4) 0.4054(3) 0.0051(2) 0.0759(12) Uani 1 1 d . . .
H5 H 0.1928 0.4523 0.0076 0.091 Uiso 1 1 calc R . .
C28 C 0.1272(3) 0.14162(18) 0.56541(16) 0.0418(7) Uani 1 1 d . . .
C27 C -0.0621(3) 0.19088(19) 0.56769(17) 0.0450(7) Uani 1 1 d . . .
O2 O -0.10047(17) 0.18031(13) 0.25528(11) 0.0496(5) Uani 1 1 d . . .
O1 O 0.13996(17) 0.12760(13) 0.25042(11) 0.0507(5) Uani 1 1 d . . .
O3 O -0.15322(18) 0.21831(15) 0.59585(12) 0.0563(5) Uani 1 1 d . . .
F2 F -0.02898(19) 0.1129(2) 0.75107(13) 0.1059(9) Uani 1 1 d . . .
F1 F 0.0239(2) 0.26172(16) 0.74179(12) 0.0958(8) Uani 1 1 d . . .
B1 B 0.0441(4) 0.1743(3) 0.7129(2) 0.0595(10) Uani 1 1 d . . .
N2 N 0.0370(2) 0.16917(16) 0.61622(13) 0.0426(6) Uani 1 1 d . . .
N1 N 0.1743(2) 0.14733(16) 0.73416(14) 0.0492(6) Uani 1 1 d . . .
N3 N 0.2298(2) 0.11768(17) 0.59024(14) 0.0502(6) Uani 1 1 d . . .
C29 C 0.2539(3) 0.12024(19) 0.67659(18) 0.0477(7) Uani 1 1 d . . .
C31 C 0.3928(4) 0.0989(2) 0.7874(2) 0.0695(10) Uani 1 1 d . . .
H31 H 0.4672 0.0826 0.8052 0.083 Uiso 1 1 calc R . .
C30 C 0.3658(3) 0.0958(2) 0.7030(2) 0.0610(9) Uani 1 1 d . . .
H30 H 0.4214 0.0777 0.6635 0.073 Uiso 1 1 calc R . .
C32 C 0.3120(3) 0.1254(3) 0.8457(2) 0.0650(10) Uani 1 1 d . . .
H32 H 0.3298 0.1260 0.9033 0.078 Uiso 1 1 calc R . .
C33 C 0.2046(3) 0.1508(2) 0.81787(18) 0.0634(9) Uani 1 1 d . . .
H33 H 0.1501 0.1712 0.8572 0.076 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C21 O2 1.377(3) . ?
C21 C22 1.384(4) . ?
C21 C26 1.400(4) . ?
C25 C26 1.388(4) . ?
C25 C24 1.394(4) . ?
C26 O1 1.387(3) . ?
C10 C1 1.366(4) . ?
C10 C9 1.434(4) . ?
C10 C11 1.482(4) . ?
C9 C4 1.417(4) . ?
C9 C8 1.433(4) . ?
C12 C13 1.407(4) . ?
C12 C17 1.424(4) . ?
C12 C11 1.432(4) . ?
C11 C20 1.370(4) . ?
C24 C23 1.381(4) . ?
C24 C28 1.474(4) . ?
C23 C22 1.381(4) . ?
C23 C27 1.489(4) . ?
C17 C16 1.414(4) . ?
C17 C18 1.421(4) . ?
C7 C8 1.354(4) . ?
C7 C6 1.395(5) . ?
C3 C2 1.358(5) . ?
C3 C4 1.416(5) . ?
C1 O1 1.411(3) . ?
C1 C2 1.412(4) . ?
C19 C18 1.358(4) . ?
C19 C20 1.399(4) . ?
C4 C5 1.411(5) . ?
C20 O2 1.409(3) . ?
C15 C16 1.349(5) . ?
C15 C14 1.402(5) . ?
C14 C13 1.361(4) . ?
C6 C5 1.374(6) . ?
C28 N3 1.289(4) . ?
C28 N2 1.369(4) . ?
C27 O3 1.205(3) . ?
C27 N2 1.407(4) . ?
F2 B1 1.365(5) . ?
F1 B1 1.370(5) . ?
B1 N2 1.527(4) . ?
B1 N1 1.583(5) . ?
N1 C29 1.347(4) . ?
N1 C33 1.365(4) . ?
N3 C29 1.389(3) . ?
C29 C30 1.396(4) . ?
C31 C32 1.362(5) . ?
C31 C30 1.366(4) . ?
C32 C33 1.360(5) . ?

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
O2 C21 C22 116.7(2) . . ?
O2 C21 C26 122.6(2) . . ?
C22 C21 C26 120.6(2) . . ?
C26 C25 C24 117.0(3) . . ?
O1 C26 C25 116.9(2) . . ?
O1 C26 C21 121.5(2) . . ?
C25 C26 C21 121.6(2) . . ?
C1 C10 C9 118.0(3) . . ?
C1 C10 C11 118.1(2) . . ?
C9 C10 C11 123.7(3) . . ?
C4 C9 C8 118.2(3) . . ?
C4 C9 C10 119.4(3) . . ?
C8 C9 C10 122.4(3) . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 C11 122.9(3) . . ?
C17 C12 C11 118.8(3) . . ?
C20 C11 C12 118.4(3) . . ?
C20 C11 C10 117.8(2) . . ?
C12 C11 C10 123.7(2) . . ?
C23 C24 C25 121.1(3) . . ?
C23 C24 C28 107.4(2) . . ?
C25 C24 C28 131.4(3) . . ?
C22 C23 C24 121.9(3) . . ?
C22 C23 C27 129.8(3) . . ?
C24 C23 C27 108.3(2) . . ?
C16 C17 C18 122.0(3) . . ?
C16 C17 C12 118.7(3) . . ?
C18 C17 C12 119.4(3) . . ?
C23 C22 C21 117.6(3) . . ?
C8 C7 C6 120.4(3) . . ?
C2 C3 C4 121.6(3) . . ?
C10 C1 O1 119.4(3) . . ?
C10 C1 C2 123.4(3) . . ?
O1 C1 C2 117.0(3) . . ?
C18 C19 C20 119.0(3) . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 C9 119.4(3) . . ?
C3 C4 C9 119.1(3) . . ?
C11 C20 C19 123.4(3) . . ?
C11 C20 O2 118.8(3) . . ?
C19 C20 O2 117.7(3) . . ?
C16 C15 C14 121.1(3) . . ?
C7 C8 C9 121.0(3) . . ?
C13 C14 C15 119.6(3) . . ?
C5 C6 C7 120.9(3) . . ?
C15 C16 C17 120.7(3) . . ?
C3 C2 C1 118.4(3) . . ?
C19 C18 C17 121.1(3) . . ?
C14 C13 C12 121.5(3) . . ?
C6 C5 C4 120.2(3) . . ?
N3 C28 N2 126.4(2) . . ?
N3 C28 C24 125.9(2) . . ?
N2 C28 C24 107.8(2) . . ?
O3 C27 N2 125.2(3) . . ?
O3 C27 C23 129.4(3) . . ?
N2 C27 C23 105.4(2) . . ?
C21 O2 C20 117.3(2) . . ?
C26 O1 C1 116.5(2) . . ?
F2 B1 F1 110.9(3) . . ?
F2 B1 N2 112.0(3) . . ?
F1 B1 N2 111.6(3) . . ?
F2 B1 N1 109.0(3) . . ?
F1 B1 N1 108.6(3) . . ?
N2 B1 N1 104.4(3) . . ?
C28 N2 C27 111.1(2) . . ?
C28 N2 B1 123.9(3) . . ?
C27 N2 B1 125.0(3) . . ?
C29 N1 C33 119.3(3) . . ?
C29 N1 B1 124.8(2) . . ?
C33 N1 B1 115.9(3) . . ?
C28 N3 C29 118.2(3) . . ?
N1 C29 N3 122.2(3) . . ?
N1 C29 C30 119.9(3) . . ?
N3 C29 C30 118.0(3) . . ?
C32 C31 C30 120.8(3) . . ?
C31 C30 C29 119.4(3) . . ?
C33 C32 C31 118.5(3) . . ?
C32 C33 N1 122.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.035
