# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_p
_database_code_depnum_ccdc_archive 'CCDC 1045034'
_audit_update_record             
;
2015-01-23 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 B F2 N2 O2'
_chemical_formula_weight         368.18

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   8.3643(17)
_cell_length_b                   9.794(2)
_cell_length_c                   11.596(2)
_cell_angle_alpha                79.79(3)
_cell_angle_beta                 71.08(3)
_cell_angle_gamma                87.20(3)
_cell_volume                     884.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9817
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7041
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3106
_reflns_number_gt                1832
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_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)+(0.1520P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.040(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3106
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.2612
_refine_ls_wR_factor_gt          0.1890
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_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 1.2871(5) 0.0767(4) 0.0859(3) 0.0356(9) Uani 1 1 d . . .
C2 C 1.1250(4) 0.1315(4) 0.1522(3) 0.0345(9) Uani 1 1 d . . .
C3 C 0.9778(5) 0.0772(4) 0.1469(4) 0.0450(10) Uani 1 1 d . . .
H3A H 0.9845 0.0050 0.1007 0.054 Uiso 1 1 calc R . .
C4 C 0.8206(5) 0.1274(4) 0.2088(3) 0.0426(10) Uani 1 1 d . . .
H4A H 0.7210 0.0912 0.2025 0.051 Uiso 1 1 calc R . .
C5 C 0.8084(4) 0.2295(4) 0.2790(3) 0.0352(9) Uani 1 1 d . . .
C6 C 0.9547(4) 0.2838(4) 0.2859(3) 0.0356(9) Uani 1 1 d . . .
H6A H 0.9469 0.3544 0.3340 0.043 Uiso 1 1 calc R . .
C7 C 1.1125(5) 0.2355(4) 0.2230(3) 0.0375(9) Uani 1 1 d . . .
H7A H 1.2120 0.2733 0.2282 0.045 Uiso 1 1 calc R . .
C8 C 0.6391(4) 0.2823(3) 0.3452(3) 0.0326(8) Uani 1 1 d . . .
C9 C 0.5607(4) 0.3816(4) 0.2802(3) 0.0351(9) Uani 1 1 d . . .
C10 C 0.6152(5) 0.4542(4) 0.1558(3) 0.0409(10) Uani 1 1 d . . .
C11 C 0.7752(5) 0.4376(5) 0.0529(4) 0.0601(13) Uani 1 1 d . . .
H11A H 0.7755 0.5025 -0.0220 0.090 Uiso 1 1 calc R . .
H11B H 0.7817 0.3423 0.0365 0.090 Uiso 1 1 calc R . .
H11C H 0.8727 0.4570 0.0769 0.090 Uiso 1 1 calc R . .
C12 C 0.4907(5) 0.5483(4) 0.1463(3) 0.0453(10) Uani 1 1 d . . .
H12A H 0.4923 0.6121 0.0740 0.054 Uiso 1 1 calc R . .
C13 C 0.3615(5) 0.5352(4) 0.2602(3) 0.0397(9) Uani 1 1 d . . .
C14 C 0.2012(5) 0.6152(4) 0.2927(4) 0.0495(11) Uani 1 1 d . . .
H14A H 0.1353 0.5834 0.3795 0.074 Uiso 1 1 calc R . .
H14B H 0.1354 0.6005 0.2396 0.074 Uiso 1 1 calc R . .
H14C H 0.2277 0.7142 0.2802 0.074 Uiso 1 1 calc R . .
C15 C 0.3732(5) 0.2316(4) 0.6570(3) 0.0395(9) Uani 1 1 d . . .
C16 C 0.2160(5) 0.2650(5) 0.7534(4) 0.0501(11) Uani 1 1 d . . .
H16A H 0.1497 0.3320 0.7148 0.075 Uiso 1 1 calc R . .
H16B H 0.2459 0.3049 0.8155 0.075 Uiso 1 1 calc R . .
H16C H 0.1492 0.1800 0.7933 0.075 Uiso 1 1 calc R . .
C17 C 0.5022(5) 0.1414(4) 0.6715(4) 0.0495(11) Uani 1 1 d . . .
H17A H 0.5066 0.0898 0.7479 0.059 Uiso 1 1 calc R . .
C18 C 0.6227(5) 0.1386(4) 0.5575(3) 0.0394(9) Uani 1 1 d . . .
C19 C 0.7781(6) 0.0528(5) 0.5354(4) 0.0549(12) Uani 1 1 d . . .
H19A H 0.7809 -0.0024 0.6139 0.082 Uiso 1 1 calc R . .
H19B H 0.8780 0.1135 0.4997 0.082 Uiso 1 1 calc R . .
H19C H 0.7777 -0.0093 0.4778 0.082 Uiso 1 1 calc R . .
C20 C 0.5666(4) 0.2329(4) 0.4715(3) 0.0350(9) Uani 1 1 d . . .
N1 N 0.4110(4) 0.2867(3) 0.5367(3) 0.0341(8) Uani 1 1 d . . .
N2 N 0.4025(4) 0.4357(3) 0.3421(3) 0.0355(8) Uani 1 1 d . . .
F1 F 0.2412(3) 0.4932(2) 0.53972(18) 0.0472(7) Uani 1 1 d . . .
F2 F 0.1559(3) 0.3089(2) 0.48057(18) 0.0444(6) Uani 1 1 d . . .
B1 B 0.2975(5) 0.3827(4) 0.4758(4) 0.0361(10) Uani 1 1 d . . .
O1 O 1.4218(3) 0.1320(3) 0.0900(2) 0.0466(8) Uani 1 1 d . . .
H1A H 1.5105 0.0926 0.0505 0.056 Uiso 1 1 d R . .
O2 O 1.2943(3) -0.0211(3) 0.0279(3) 0.0542(8) 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
C1 O2 1.252(4) . ?
C1 O1 1.291(4) . ?
C1 C2 1.456(5) . ?
C2 C3 1.388(5) . ?
C2 C7 1.398(5) . ?
C3 C4 1.391(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.378(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.388(5) . ?
C5 C8 1.492(5) . ?
C6 C7 1.391(5) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C9 1.394(5) . ?
C8 C20 1.396(5) . ?
C9 N2 1.413(4) . ?
C9 C10 1.426(5) . ?
C10 C12 1.375(5) . ?
C10 C11 1.501(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.399(5) . ?
C12 H12A 0.9500 . ?
C13 N2 1.349(5) . ?
C13 C14 1.492(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N1 1.342(4) . ?
C15 C17 1.395(6) . ?
C15 C16 1.490(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.382(5) . ?
C17 H17A 0.9500 . ?
C18 C20 1.415(5) . ?
C18 C19 1.489(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N1 1.407(4) . ?
N1 B1 1.548(5) . ?
N2 B1 1.523(5) . ?
F1 B1 1.397(4) . ?
F2 B1 1.399(5) . ?
O1 H1A 0.8500 . ?

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 C1 O1 121.7(3) . . ?
O2 C1 C2 120.8(3) . . ?
O1 C1 C2 117.5(3) . . ?
C3 C2 C7 118.9(3) . . ?
C3 C2 C1 119.0(3) . . ?
C7 C2 C1 122.1(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 C8 119.9(3) . . ?
C6 C5 C8 120.6(3) . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6A 119.7 . . ?
C7 C6 H6A 119.7 . . ?
C6 C7 C2 120.1(3) . . ?
C6 C7 H7A 120.0 . . ?
C2 C7 H7A 120.0 . . ?
C9 C8 C20 122.2(3) . . ?
C9 C8 C5 119.2(3) . . ?
C20 C8 C5 118.6(3) . . ?
C8 C9 N2 120.0(3) . . ?
C8 C9 C10 132.0(3) . . ?
N2 C9 C10 107.8(3) . . ?
C12 C10 C9 106.1(3) . . ?
C12 C10 C11 124.9(3) . . ?
C9 C10 C11 129.0(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 C13 109.1(3) . . ?
C10 C12 H12A 125.4 . . ?
C13 C12 H12A 125.4 . . ?
N2 C13 C12 109.3(3) . . ?
N2 C13 C14 122.9(3) . . ?
C12 C13 C14 127.9(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C17 108.4(3) . . ?
N1 C15 C16 123.1(3) . . ?
C17 C15 C16 128.4(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 109.5(3) . . ?
C18 C17 H17A 125.3 . . ?
C15 C17 H17A 125.3 . . ?
C17 C18 C20 105.7(3) . . ?
C17 C18 C19 125.2(4) . . ?
C20 C18 C19 129.1(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 C20 N1 119.3(3) . . ?
C8 C20 C18 132.7(3) . . ?
N1 C20 C18 107.8(3) . . ?
C15 N1 C20 108.5(3) . . ?
C15 N1 B1 126.6(3) . . ?
C20 N1 B1 124.7(3) . . ?
C13 N2 C9 107.7(3) . . ?
C13 N2 B1 127.7(3) . . ?
C9 N2 B1 124.5(3) . . ?
F1 B1 F2 108.1(3) . . ?
F1 B1 N2 110.6(3) . . ?
F2 B1 N2 110.5(3) . . ?
F1 B1 N1 109.9(3) . . ?
F2 B1 N1 109.9(3) . . ?
N2 B1 N1 107.7(3) . . ?
C1 O1 H1A 111.4 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1045035'
_audit_update_record             
;
2015-01-23 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 B F2 I2 N2 O2'
_chemical_formula_weight         619.97

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   7.7470(19)
_cell_length_b                   10.414(3)
_cell_length_c                   14.007(3)
_cell_angle_alpha                91.746(4)
_cell_angle_beta                 105.965(4)
_cell_angle_gamma                91.149(5)
_cell_volume                     1085.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    2.932
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5398
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3713
_reflns_number_gt                3291
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_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)+(0.0874P)²+0.7588P] 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         3713
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
I1 I 0.57522(9) -0.17651(5) -0.39634(4) 0.0689(2) Uani 1 1 d . . .
I2 I 0.38967(6) 0.47208(4) 0.18043(3) 0.0516(2) Uani 1 1 d . . .
C1 C -0.2990(7) 0.4112(5) -0.4234(4) 0.0324(11) Uani 1 1 d . . .
C2 C -0.1383(7) 0.3492(5) -0.3641(4) 0.0337(12) Uani 1 1 d . . .
C3 C -0.1546(7) 0.2618(5) -0.2929(4) 0.0322(11) Uani 1 1 d . . .
H3A H -0.2695 0.2378 -0.2862 0.039 Uiso 1 1 calc R . .
C4 C -0.0027(7) 0.2117(5) -0.2332(4) 0.0324(11) Uani 1 1 d . . .
H4A H -0.0126 0.1540 -0.1835 0.039 Uiso 1 1 calc R . .
C5 C 0.1647(7) 0.2432(5) -0.2436(4) 0.0324(11) Uani 1 1 d . . .
C6 C 0.1801(8) 0.3271(6) -0.3160(4) 0.0433(14) Uani 1 1 d . . .
H6A H 0.2947 0.3482 -0.3245 0.052 Uiso 1 1 calc R . .
C7 C 0.0290(8) 0.3792(6) -0.3751(4) 0.0446(15) Uani 1 1 d . . .
H7A H 0.0395 0.4370 -0.4245 0.054 Uiso 1 1 calc R . .
C8 C 0.3323(7) 0.1967(5) -0.1743(4) 0.0307(11) Uani 1 1 d . . .
C9 C 0.3884(7) 0.2517(5) -0.0793(4) 0.0286(11) Uani 1 1 d . . .
C10 C 0.3151(7) 0.3472(5) -0.0290(4) 0.0322(12) Uani 1 1 d . . .
C11 C 0.1541(9) 0.4275(6) -0.0678(5) 0.0433(14) Uani 1 1 d . . .
H11A H 0.1388 0.4852 -0.0144 0.065 Uiso 1 1 calc R . .
H11B H 0.0469 0.3713 -0.0922 0.065 Uiso 1 1 calc R . .
H11C H 0.1713 0.4784 -0.1224 0.065 Uiso 1 1 calc R . .
C12 C 0.4275(9) 0.3562(5) 0.0661(4) 0.0369(13) Uani 1 1 d . . .
C13 C 0.5706(8) 0.2723(5) 0.0747(4) 0.0335(12) Uani 1 1 d . . .
C14 C 0.7231(9) 0.2535(6) 0.1621(4) 0.0440(14) Uani 1 1 d . . .
H14A H 0.8011 0.1884 0.1457 0.066 Uiso 1 1 calc R . .
H14B H 0.6783 0.2248 0.2171 0.066 Uiso 1 1 calc R . .
H14C H 0.7914 0.3348 0.1816 0.066 Uiso 1 1 calc R . .
C15 C 0.6568(8) -0.0281(5) -0.1953(5) 0.0384(13) Uani 1 1 d . . .
C16 C 0.8271(9) -0.0942(6) -0.1509(5) 0.0481(15) Uani 1 1 d . . .
H16A H 0.8824 -0.0582 -0.0837 0.072 Uiso 1 1 calc R . .
H16B H 0.9097 -0.0817 -0.1919 0.072 Uiso 1 1 calc R . .
H16C H 0.8016 -0.1863 -0.1478 0.072 Uiso 1 1 calc R . .
C17 C 0.5374(9) -0.0486(6) -0.2888(5) 0.0423(14) Uani 1 1 d . . .
C18 C 0.3932(9) 0.0291(6) -0.2986(4) 0.0426(14) Uani 1 1 d . . .
C19 C 0.2294(11) 0.0275(8) -0.3857(5) 0.0612(19) Uani 1 1 d . . .
H19A H 0.2447 -0.0335 -0.4373 0.092 Uiso 1 1 calc R . .
H19B H 0.2125 0.1136 -0.4125 0.092 Uiso 1 1 calc R . .
H19C H 0.1240 0.0013 -0.3645 0.092 Uiso 1 1 calc R . .
C20 C 0.4292(7) 0.1018(5) -0.2067(4) 0.0313(11) Uani 1 1 d . . .
N1 N 0.5917(6) 0.0625(4) -0.1459(3) 0.0323(10) Uani 1 1 d . . .
N2 N 0.5469(6) 0.2103(4) -0.0131(3) 0.0311(10) Uani 1 1 d . . .
B1 B 0.6822(8) 0.1180(6) -0.0399(5) 0.0315(13) Uani 1 1 d . . .
F1 F 0.8371(4) 0.1867(3) -0.0388(2) 0.0404(8) Uani 1 1 d . . .
F2 F 0.7213(5) 0.0202(3) 0.0261(2) 0.0418(8) Uani 1 1 d . . .
O1 O -0.2716(5) 0.4853(4) -0.4906(3) 0.0501(11) Uani 1 1 d . . .
H1A H -0.3668 0.5223 -0.5209 0.060 Uiso 1 1 d R . .
O2 O -0.4472(5) 0.3942(4) -0.4092(3) 0.0359(9) 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
I1 C17 2.066(6) . ?
I2 C12 2.064(6) . ?
C1 O2 1.229(6) . ?
C1 O1 1.293(6) . ?
C1 C2 1.467(8) . ?
C2 C7 1.377(8) . ?
C2 C3 1.400(7) . ?
C3 C4 1.367(8) . ?
C4 C5 1.379(7) . ?
C5 C6 1.387(7) . ?
C5 C8 1.491(7) . ?
C6 C7 1.368(8) . ?
C8 C9 1.384(7) . ?
C8 C20 1.391(8) . ?
C9 N2 1.404(7) . ?
C9 C10 1.417(7) . ?
C10 C12 1.376(8) . ?
C10 C11 1.499(8) . ?
C12 C13 1.407(9) . ?
C13 N2 1.336(7) . ?
C13 C14 1.469(8) . ?
C15 N1 1.340(8) . ?
C15 C17 1.387(9) . ?
C15 C16 1.487(8) . ?
C17 C18 1.372(9) . ?
C18 C20 1.428(8) . ?
C18 C19 1.499(10) . ?
C20 N1 1.389(7) . ?
N1 B1 1.546(8) . ?
N2 B1 1.549(8) . ?
B1 F1 1.380(6) . ?
B1 F2 1.379(7) . ?

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 C1 O1 123.1(5) . . ?
O2 C1 C2 122.1(5) . . ?
O1 C1 C2 114.8(5) . . ?
C7 C2 C3 119.6(5) . . ?
C7 C2 C1 120.9(5) . . ?
C3 C2 C1 119.5(5) . . ?
C4 C3 C2 119.0(5) . . ?
C3 C4 C5 121.2(5) . . ?
C4 C5 C6 119.7(5) . . ?
C4 C5 C8 121.7(5) . . ?
C6 C5 C8 118.5(5) . . ?
C7 C6 C5 119.5(5) . . ?
C6 C7 C2 121.0(5) . . ?
C9 C8 C20 121.9(5) . . ?
C9 C8 C5 118.3(5) . . ?
C20 C8 C5 119.7(5) . . ?
C8 C9 N2 119.3(5) . . ?
C8 C9 C10 132.7(5) . . ?
N2 C9 C10 108.0(5) . . ?
C12 C10 C9 105.4(5) . . ?
C12 C10 C11 125.2(5) . . ?
C9 C10 C11 129.4(5) . . ?
C10 C12 C13 109.8(5) . . ?
C10 C12 I2 125.3(5) . . ?
C13 C12 I2 124.9(4) . . ?
N2 C13 C12 107.8(5) . . ?
N2 C13 C14 124.2(6) . . ?
C12 C13 C14 128.0(5) . . ?
N1 C15 C17 108.5(5) . . ?
N1 C15 C16 123.0(6) . . ?
C17 C15 C16 128.5(6) . . ?
C18 C17 C15 109.8(5) . . ?
C18 C17 I1 125.7(5) . . ?
C15 C17 I1 124.5(5) . . ?
C17 C18 C20 105.2(6) . . ?
C17 C18 C19 125.7(6) . . ?
C20 C18 C19 129.0(6) . . ?
N1 C20 C8 120.9(5) . . ?
N1 C20 C18 107.8(5) . . ?
C8 C20 C18 131.3(5) . . ?
C15 N1 C20 108.7(5) . . ?
C15 N1 B1 126.4(5) . . ?
C20 N1 B1 124.9(5) . . ?
C13 N2 C9 108.9(5) . . ?
C13 N2 B1 125.1(5) . . ?
C9 N2 B1 125.7(4) . . ?
F1 B1 F2 110.2(5) . . ?
F1 B1 N1 109.9(4) . . ?
F2 B1 N1 110.2(5) . . ?
F1 B1 N2 109.1(5) . . ?
F2 B1 N2 110.8(4) . . ?
N1 B1 N2 106.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         1.254
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.150
####################################################################### 
# 
# 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_eisgl01
_database_code_depnum_ccdc_archive 'CCDC 1045036'
_audit_update_record             
;
2015-01-23 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 B F2 I2 N2 O2'
_chemical_formula_weight         633.99

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   10.0744(9)
_cell_length_b                   10.4080(10)
_cell_length_c                   11.8050(11)
_cell_angle_alpha                69.844(2)
_cell_angle_beta                 85.884(2)
_cell_angle_gamma                68.191(2)
_cell_volume                     1076.58(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.956
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    2.959
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.4913
_exptl_absorpt_correction_T_max  0.5891
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24030
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         35.63
_reflns_number_total             9766
_reflns_number_gt                8491
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_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)+(0.0204P)²+0.4710P] 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         9766
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0533
_refine_ls_wR_factor_gt          0.0513
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.004
_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
I1 I 0.276784(10) 1.018595(10) 1.216104(8) 0.01455(2) Uani 1 1 d . . .
I2 I 0.762761(10) 0.407561(11) 0.615509(9) 0.01708(2) Uani 1 1 d . . .
C1 C 0.57821(16) 0.68766(18) 1.24473(13) 0.0172(3) Uani 1 1 d . . .
H1A H 0.6800 0.6643 1.2298 0.026 Uiso 1 1 calc R . .
H1B H 0.5608 0.5960 1.2829 0.026 Uiso 1 1 calc R . .
H1C H 0.5514 0.7459 1.2984 0.026 Uiso 1 1 calc R . .
C2 C 0.49083(15) 0.77374(16) 1.12796(12) 0.0126(2) Uani 1 1 d . . .
C3 C 0.36969(15) 0.90545(15) 1.09890(12) 0.0130(2) Uani 1 1 d . . .
C4 C 0.32251(15) 0.94870(15) 0.97885(12) 0.0122(2) Uani 1 1 d . . .
C5 C 0.19672(16) 1.08373(16) 0.91478(14) 0.0172(3) Uani 1 1 d . . .
H5A H 0.1829 1.1594 0.9507 0.026 Uiso 1 1 calc R . .
H5B H 0.1107 1.0593 0.9226 0.026 Uiso 1 1 calc R . .
H5C H 0.2141 1.1210 0.8290 0.026 Uiso 1 1 calc R . .
C6 C 0.41741(14) 0.83805(15) 0.93507(12) 0.0114(2) Uani 1 1 d . . .
C7 C 0.42152(14) 0.82056(14) 0.82214(12) 0.0109(2) Uani 1 1 d . . .
C8 C 0.52568(14) 0.70109(14) 0.79985(12) 0.0109(2) Uani 1 1 d . . .
C9 C 0.45122(16) 0.71949(17) 0.58276(13) 0.0160(2) Uani 1 1 d . . .
H9A H 0.4835 0.6523 0.5366 0.024 Uiso 1 1 calc R . .
H9B H 0.4572 0.8146 0.5342 0.024 Uiso 1 1 calc R . .
H9C H 0.3518 0.7338 0.6028 0.024 Uiso 1 1 calc R . .
C10 C 0.54447(15) 0.65519(15) 0.69663(12) 0.0121(2) Uani 1 1 d . . .
C11 C 0.66542(15) 0.52691(15) 0.72726(13) 0.0133(2) Uani 1 1 d . . .
C12 C 0.71587(15) 0.49136(15) 0.84692(12) 0.0131(2) Uani 1 1 d . . .
C13 C 0.83665(16) 0.35878(16) 0.91961(14) 0.0175(3) Uani 1 1 d . . .
H13A H 0.8791 0.3835 0.9775 0.026 Uiso 1 1 calc R . .
H13B H 0.9094 0.3249 0.8658 0.026 Uiso 1 1 calc R . .
H13C H 0.8012 0.2804 0.9635 0.026 Uiso 1 1 calc R . .
C14 C 0.31469(14) 0.93194(15) 0.72183(12) 0.0115(2) Uani 1 1 d . . .
C15 C 0.17516(15) 0.93677(16) 0.71966(12) 0.0136(2) Uani 1 1 d . . .
H15A H 0.1455 0.8709 0.7844 0.016 Uiso 1 1 calc R . .
C16 C 0.07903(15) 1.03820(16) 0.62252(12) 0.0135(2) Uani 1 1 d . . .
H16A H -0.0170 1.0432 0.6217 0.016 Uiso 1 1 calc R . .
C17 C 0.12375(14) 1.13258(15) 0.52620(12) 0.0120(2) Uani 1 1 d . . .
C18 C 0.26358(15) 1.12873(16) 0.52867(13) 0.0152(2) Uani 1 1 d . . .
H18A H 0.2936 1.1939 0.4635 0.018 Uiso 1 1 calc R . .
C19 C 0.35827(15) 1.02925(17) 0.62676(13) 0.0158(2) Uani 1 1 d . . .
H19A H 0.4531 1.0272 0.6294 0.019 Uiso 1 1 calc R . .
C20 C 0.01930(14) 1.23706(15) 0.42260(12) 0.0121(2) Uani 1 1 d . . .
C21 C -0.01053(17) 1.38967(18) 0.21833(14) 0.0204(3) Uani 1 1 d . . .
H21A H 0.0430 1.3973 0.1452 0.031 Uiso 1 1 calc R . .
H21B H -0.0500 1.4858 0.2291 0.031 Uiso 1 1 calc R . .
H21C H -0.0889 1.3584 0.2104 0.031 Uiso 1 1 calc R . .
N1 N 0.51864(12) 0.73394(13) 1.02866(10) 0.01205(19) Uani 1 1 d . . .
N2 N 0.63188(12) 0.59693(13) 0.88941(10) 0.01128(19) Uani 1 1 d . . .
F1 F 0.65504(10) 0.47169(10) 1.10491(8) 0.01606(16) Uani 1 1 d . . .
F2 F 0.77623(9) 0.62464(10) 1.02716(8) 0.01424(15) Uani 1 1 d . . .
O1 O -0.10900(11) 1.27438(13) 0.42742(10) 0.0175(2) Uani 1 1 d . . .
O2 O 0.08449(11) 1.28240(12) 0.32230(9) 0.01670(19) Uani 1 1 d . . .
B1 B 0.64968(16) 0.60269(17) 1.01679(13) 0.0119(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
I1 C3 2.0725(13) . ?
I2 C11 2.0697(13) . ?
C1 C2 1.488(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.3511(17) . ?
C2 C3 1.4069(19) . ?
C3 C4 1.3911(19) . ?
C4 C6 1.4242(19) . ?
C4 C5 1.495(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N1 1.3966(17) . ?
C6 C7 1.4021(18) . ?
C7 C8 1.3903(19) . ?
C7 C14 1.4881(18) . ?
C8 N2 1.3958(17) . ?
C8 C10 1.4317(18) . ?
C9 C10 1.494(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.3855(19) . ?
C11 C12 1.4120(19) . ?
C12 N2 1.3427(18) . ?
C12 C13 1.486(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3896(19) . ?
C14 C19 1.398(2) . ?
C15 C16 1.3902(19) . ?
C15 H15A 0.9500 . ?
C16 C17 1.395(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.3965(19) . ?
C17 C20 1.4844(19) . ?
C18 C19 1.3861(19) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 O1 1.2069(17) . ?
C20 O2 1.3377(17) . ?
C21 O2 1.4490(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 B1 1.5472(19) . ?
N2 B1 1.5511(19) . ?
F1 B1 1.3856(18) . ?
F2 B1 1.3966(18) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 107.96(12) . . ?
N1 C2 C1 123.44(12) . . ?
C3 C2 C1 128.60(13) . . ?
C4 C3 C2 109.41(12) . . ?
C4 C3 I1 125.22(10) . . ?
C2 C3 I1 125.37(10) . . ?
C3 C4 C6 105.38(12) . . ?
C3 C4 C5 125.17(12) . . ?
C6 C4 C5 129.45(12) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 120.19(12) . . ?
N1 C6 C4 108.27(11) . . ?
C7 C6 C4 131.54(12) . . ?
C8 C7 C6 121.45(12) . . ?
C8 C7 C14 118.17(12) . . ?
C6 C7 C14 120.37(12) . . ?
C7 C8 N2 120.34(12) . . ?
C7 C8 C10 131.15(12) . . ?
N2 C8 C10 108.44(11) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 105.11(12) . . ?
C11 C10 C9 125.28(12) . . ?
C8 C10 C9 129.43(13) . . ?
C10 C11 C12 109.26(12) . . ?
C10 C11 I2 126.11(10) . . ?
C12 C11 I2 124.61(10) . . ?
N2 C12 C11 108.42(12) . . ?
N2 C12 C13 123.70(13) . . ?
C11 C12 C13 127.84(13) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.10(12) . . ?
C15 C14 C7 121.05(12) . . ?
C19 C14 C7 118.81(12) . . ?
C14 C15 C16 119.89(13) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
C15 C16 C17 119.94(12) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C16 C17 C18 120.23(12) . . ?
C16 C17 C20 118.53(12) . . ?
C18 C17 C20 121.24(12) . . ?
C19 C18 C17 119.59(13) . . ?
C19 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
C18 C19 C14 120.21(13) . . ?
C18 C19 H19A 119.9 . . ?
C14 C19 H19A 119.9 . . ?
O1 C20 O2 123.95(13) . . ?
O1 C20 C17 124.15(13) . . ?
O2 C20 C17 111.89(11) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 N1 C6 108.98(11) . . ?
C2 N1 B1 125.45(11) . . ?
C6 N1 B1 125.33(11) . . ?
C12 N2 C8 108.72(11) . . ?
C12 N2 B1 125.78(11) . . ?
C8 N2 B1 125.51(11) . . ?
C20 O2 C21 115.17(12) . . ?
F1 B1 F2 109.20(11) . . ?
F1 B1 N1 110.94(11) . . ?
F2 B1 N1 110.28(11) . . ?
F1 B1 N2 110.04(11) . . ?
F2 B1 N2 109.70(11) . . ?
N1 B1 N2 106.65(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -0.58(16) . . . . ?
C1 C2 C3 C4 179.31(14) . . . . ?
N1 C2 C3 I1 179.88(10) . . . . ?
C1 C2 C3 I1 -0.2(2) . . . . ?
C2 C3 C4 C6 0.81(16) . . . . ?
I1 C3 C4 C6 -179.65(10) . . . . ?
C2 C3 C4 C5 -179.72(13) . . . . ?
I1 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C6 N1 -0.75(15) . . . . ?
C5 C4 C6 N1 179.82(14) . . . . ?
C3 C4 C6 C7 178.56(14) . . . . ?
C5 C4 C6 C7 -0.9(3) . . . . ?
N1 C6 C7 C8 -0.4(2) . . . . ?
C4 C6 C7 C8 -179.65(14) . . . . ?
N1 C6 C7 C14 -179.43(12) . . . . ?
C4 C6 C7 C14 1.3(2) . . . . ?
C6 C7 C8 N2 -1.7(2) . . . . ?
C14 C7 C8 N2 177.31(12) . . . . ?
C6 C7 C8 C10 174.75(14) . . . . ?
C14 C7 C8 C10 -6.2(2) . . . . ?
C7 C8 C10 C11 -178.91(14) . . . . ?
N2 C8 C10 C11 -2.10(15) . . . . ?
C7 C8 C10 C9 -3.6(2) . . . . ?
N2 C8 C10 C9 173.19(14) . . . . ?
C8 C10 C11 C12 2.45(16) . . . . ?
C9 C10 C11 C12 -173.10(13) . . . . ?
C8 C10 C11 I2 -175.80(10) . . . . ?
C9 C10 C11 I2 8.7(2) . . . . ?
C10 C11 C12 N2 -1.96(17) . . . . ?
I2 C11 C12 N2 176.32(10) . . . . ?
C10 C11 C12 C13 175.74(14) . . . . ?
I2 C11 C12 C13 -6.0(2) . . . . ?
C8 C7 C14 C15 104.30(16) . . . . ?
C6 C7 C14 C15 -76.65(17) . . . . ?
C8 C7 C14 C19 -73.47(17) . . . . ?
C6 C7 C14 C19 105.59(16) . . . . ?
C19 C14 C15 C16 0.2(2) . . . . ?
C7 C14 C15 C16 -177.50(13) . . . . ?
C14 C15 C16 C17 1.5(2) . . . . ?
C15 C16 C17 C18 -2.0(2) . . . . ?
C15 C16 C17 C20 178.55(13) . . . . ?
C16 C17 C18 C19 0.8(2) . . . . ?
C20 C17 C18 C19 -179.75(14) . . . . ?
C17 C18 C19 C14 0.9(2) . . . . ?
C15 C14 C19 C18 -1.4(2) . . . . ?
C7 C14 C19 C18 176.35(13) . . . . ?
C16 C17 C20 O1 20.2(2) . . . . ?
C18 C17 C20 O1 -159.29(15) . . . . ?
C16 C17 C20 O2 -158.39(13) . . . . ?
C18 C17 C20 O2 22.15(19) . . . . ?
C3 C2 N1 C6 0.10(16) . . . . ?
C1 C2 N1 C6 -179.80(13) . . . . ?
C3 C2 N1 B1 174.73(13) . . . . ?
C1 C2 N1 B1 -5.2(2) . . . . ?
C7 C6 N1 C2 -178.99(12) . . . . ?
C4 C6 N1 C2 0.41(16) . . . . ?
C7 C6 N1 B1 6.4(2) . . . . ?
C4 C6 N1 B1 -174.23(12) . . . . ?
C11 C12 N2 C8 0.58(16) . . . . ?
C13 C12 N2 C8 -177.25(13) . . . . ?
C11 C12 N2 B1 -179.34(12) . . . . ?
C13 C12 N2 B1 2.8(2) . . . . ?
C7 C8 N2 C12 178.18(12) . . . . ?
C10 C8 N2 C12 0.96(15) . . . . ?
C7 C8 N2 B1 -1.9(2) . . . . ?
C10 C8 N2 B1 -179.12(12) . . . . ?
O1 C20 O2 C21 4.0(2) . . . . ?
C17 C20 O2 C21 -177.49(12) . . . . ?
C2 N1 B1 F1 57.79(18) . . . . ?
C6 N1 B1 F1 -128.43(13) . . . . ?
C2 N1 B1 F2 -63.33(17) . . . . ?
C6 N1 B1 F2 110.46(14) . . . . ?
C2 N1 B1 N2 177.62(12) . . . . ?
C6 N1 B1 N2 -8.59(18) . . . . ?
C12 N2 B1 F1 -53.31(18) . . . . ?
C8 N2 B1 F1 126.79(13) . . . . ?
C12 N2 B1 F2 66.85(17) . . . . ?
C8 N2 B1 F2 -113.05(14) . . . . ?
C12 N2 B1 N1 -173.72(12) . . . . ?
C8 N2 B1 N1 6.38(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        35.63
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.003
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.111
