# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_140620_xiamindmn
_database_code_depnum_ccdc_archive 'CCDC 1010944'
_audit_update_record             
;
2014-06-29 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;
_audit_creation_date             2014-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(Z)-1-(4-(dimethylamino)phenyl)-2-(phenanthridin-6-yl)ethenol difluoroboron'
_chemical_formula_moiety         'C23 H19 B F2 N2 O'
_chemical_formula_sum            'C23 H19 B F2 N2 O'
_chemical_formula_weight         388.21
_chemical_melting_point          468.8-470.2
_chemical_oxdiff_formula         'c10 h10 n2 o8 B1 F1'
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   7.2856(5)
_cell_length_b                   18.1056(11)
_cell_length_c                   27.2497(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3594.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2651
_cell_measurement_temperature    171.2
_cell_measurement_theta_max      29.3929
_cell_measurement_theta_min      3.0990
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10804
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.11
_diffrn_ambient_temperature      171.2
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0100700000
_diffrn_orient_matrix_UB_12      -0.0216512000
_diffrn_orient_matrix_UB_13      -0.0215289000
_diffrn_orient_matrix_UB_21      -0.0423396000
_diffrn_orient_matrix_UB_22      0.0302641000
_diffrn_orient_matrix_UB_23      -0.0120137000
_diffrn_orient_matrix_UB_31      0.0871143000
_diffrn_orient_matrix_UB_32      0.0122299000
_diffrn_orient_matrix_UB_33      -0.0083420000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2426
_reflns_number_total             3284
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0474P)²+0.3002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1039
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C17(H17), C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.76247(14) -0.08701(6) 0.10049(3) 0.0355(3) Uani 1 d . . .
F2 F 1.05995(13) -0.12064(6) 0.11016(3) 0.0324(3) Uani 1 d . . .
O1 O 0.9868(2) 0.00163(7) 0.09702(4) 0.0378(4) Uani 1 d . . .
N1 N 0.91377(18) -0.05823(7) 0.17809(5) 0.0215(3) Uani 1 d . . .
N2 N 1.0979(2) 0.31230(8) -0.00458(5) 0.0331(4) Uani 1 d . . .
C1 C 0.8063(2) -0.18572(9) 0.18295(7) 0.0269(4) Uani 1 d . . .
H1 H 0.8095 -0.1890 0.1482 0.032 Uiso 1 calc . . R
C2 C 0.7514(2) -0.24545(9) 0.21028(7) 0.0289(4) Uani 1 d . . .
H2 H 0.7182 -0.2900 0.1942 0.035 Uiso 1 calc . . R
C3 C 0.7438(3) -0.24174(9) 0.26112(7) 0.0287(4) Uani 1 d . . .
H3 H 0.7044 -0.2832 0.2797 0.034 Uiso 1 calc . . R
C4 C 0.7936(2) -0.17759(9) 0.28429(6) 0.0253(4) Uani 1 d . . .
H4 H 0.7875 -0.1750 0.3191 0.030 Uiso 1 calc . . R
C5 C 0.8533(2) -0.11574(9) 0.25779(6) 0.0206(4) Uani 1 d . . .
C6 C 0.8577(2) -0.11969(9) 0.20632(6) 0.0220(4) Uani 1 d . . .
C7 C 0.9075(2) -0.04746(9) 0.28194(6) 0.0195(4) Uani 1 d . . .
C8 C 0.9148(2) -0.04049(9) 0.33337(6) 0.0247(4) Uani 1 d . . .
H8 H 0.8862 -0.0819 0.3534 0.030 Uiso 1 calc . . R
C9 C 0.9625(2) 0.02502(10) 0.35501(6) 0.0269(4) Uani 1 d . . .
H9 H 0.9656 0.0288 0.3898 0.032 Uiso 1 calc . . R
C10 C 1.0065(3) 0.08589(9) 0.32632(6) 0.0266(4) Uani 1 d . . .
H10 H 1.0381 0.1314 0.3414 0.032 Uiso 1 calc . . R
C11 C 1.0042(2) 0.08012(9) 0.27619(6) 0.0233(4) Uani 1 d . . .
H11 H 1.0361 0.1218 0.2568 0.028 Uiso 1 calc . . R
C12 C 0.9555(2) 0.01354(9) 0.25288(6) 0.0191(4) Uani 1 d . . .
C13 C 0.9574(2) 0.00676(9) 0.19934(6) 0.0198(4) Uani 1 d . . .
C14 C 1.0042(2) 0.06779(9) 0.17000(6) 0.0220(4) Uani 1 d . . .
H14 H 1.0299 0.1134 0.1858 0.026 Uiso 1 calc . . R
C15 C 1.0147(2) 0.06507(9) 0.12004(6) 0.0234(4) Uani 1 d . . .
C16 C 1.0534(2) 0.12791(10) 0.08858(6) 0.0234(4) Uani 1 d . . .
C17 C 1.0627(2) 0.12000(10) 0.03736(6) 0.0296(4) Uani 1 d . . .
H17 H 1.0563 0.0719 0.0235 0.035 Uiso 1 calc . . R
C18 C 1.0805(3) 0.17958(10) 0.00689(6) 0.0310(5) Uani 1 d . . .
H18 H 1.0875 0.1718 -0.0275 0.037 Uiso 1 calc . . R
C19 C 1.0890(2) 0.25242(10) 0.02532(6) 0.0263(4) Uani 1 d . . .
C20 C 1.0863(3) 0.26001(10) 0.07694(6) 0.0306(5) Uani 1 d . . .
H20 H 1.0960 0.3078 0.0911 0.037 Uiso 1 calc . . R
C21 C 1.0698(2) 0.19968(10) 0.10692(6) 0.0274(4) Uani 1 d . . .
H21 H 1.0695 0.2069 0.1415 0.033 Uiso 1 calc . . R
C22 C 1.0982(3) 0.38689(11) 0.01537(7) 0.0425(5) Uani 1 d . . .
H22A H 0.9820 0.3961 0.0324 0.064 Uiso 1 calc . . GR
H22B H 1.1127 0.4226 -0.0114 0.064 Uiso 1 calc . . GR
H22C H 1.2002 0.3922 0.0386 0.064 Uiso 1 calc . . GR
C23 C 1.0881(3) 0.30451(12) -0.05744(6) 0.0400(5) Uani 1 d . . .
H23A H 0.9680 0.2844 -0.0666 0.060 Uiso 1 calc . . GR
H23B H 1.1849 0.2709 -0.0686 0.060 Uiso 1 calc . . GR
H23C H 1.1047 0.3529 -0.0729 0.060 Uiso 1 calc . . GR
B1 B 0.9298(3) -0.06681(11) 0.12011(7) 0.0259(5) Uani 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 1.381(2) . ?
F2 B1 1.386(2) . ?
O1 C15 1.324(2) . ?
O1 B1 1.451(2) . ?
N1 C6 1.413(2) . ?
N1 C13 1.349(2) . ?
N1 B1 1.592(2) . ?
N2 C19 1.358(2) . ?
N2 C22 1.456(2) . ?
N2 C23 1.449(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.372(2) . ?
C1 C6 1.405(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.371(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.402(2) . ?
C5 C6 1.405(2) . ?
C5 C7 1.455(2) . ?
C7 C8 1.408(2) . ?
C7 C12 1.403(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.369(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.370(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.408(2) . ?
C12 C13 1.464(2) . ?
C13 C14 1.406(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.364(2) . ?
C15 C16 1.452(2) . ?
C16 C17 1.405(2) . ?
C16 C21 1.397(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.367(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.413(3) . ?
C19 C20 1.413(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.369(2) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C15 O1 B1 125.40(14) . . ?
C6 N1 B1 118.99(13) . . ?
C13 N1 C6 121.42(14) . . ?
C13 N1 B1 119.58(14) . . ?
C19 N2 C22 121.12(15) . . ?
C19 N2 C23 121.09(16) . . ?
C23 N2 C22 117.49(15) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.14(16) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.01(17) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.34(17) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.45(16) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.75(15) . . ?
C4 C5 C7 122.02(15) . . ?
C6 C5 C7 119.23(15) . . ?
C1 C6 N1 120.03(15) . . ?
C5 C6 N1 120.67(14) . . ?
C5 C6 C1 119.30(15) . . ?
C8 C7 C5 122.43(15) . . ?
C12 C7 C5 118.76(15) . . ?
C12 C7 C8 118.81(15) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.04(16) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.24(15) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.86(16) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.20(16) . . ?
C12 C11 H11 119.4 . . ?
C7 C12 C11 118.82(15) . . ?
C7 C12 C13 119.92(15) . . ?
C11 C12 C13 121.26(15) . . ?
N1 C13 C12 119.89(15) . . ?
N1 C13 C14 119.90(15) . . ?
C14 C13 C12 120.21(15) . . ?
C13 C14 H14 118.2 . . ?
C15 C14 C13 123.55(16) . . ?
C15 C14 H14 118.2 . . ?
O1 C15 C14 119.70(16) . . ?
O1 C15 C16 115.44(14) . . ?
C14 C15 C16 124.86(16) . . ?
C17 C16 C15 121.06(16) . . ?
C21 C16 C15 122.27(15) . . ?
C21 C16 C17 116.50(16) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.83(17) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.66(16) . . ?
C19 C18 H18 119.2 . . ?
N2 C19 C18 122.30(16) . . ?
N2 C19 C20 121.35(17) . . ?
C18 C19 C20 116.36(16) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.17(17) . . ?
C21 C20 H20 119.4 . . ?
C16 C21 H21 118.8 . . ?
C20 C21 C16 122.40(15) . . ?
C20 C21 H21 118.8 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F1 B1 F2 110.00(15) . . ?
F1 B1 O1 108.13(15) . . ?
F1 B1 N1 110.21(15) . . ?
F2 B1 O1 108.66(15) . . ?
F2 B1 N1 108.23(14) . . ?
O1 B1 N1 111.60(14) . . ?

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
O1 C15 C16 C17 -1.0(2) . . . . ?
O1 C15 C16 C21 174.21(16) . . . . ?
N1 C13 C14 C15 -2.3(3) . . . . ?
N2 C19 C20 C21 177.32(17) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C1 C6 N1 -179.87(15) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C3 C4 C5 C7 -179.63(16) . . . . ?
C4 C5 C6 N1 178.85(15) . . . . ?
C4 C5 C6 C1 -1.4(2) . . . . ?
C4 C5 C7 C8 4.1(2) . . . . ?
C4 C5 C7 C12 -176.31(15) . . . . ?
C5 C7 C8 C9 -178.54(16) . . . . ?
C5 C7 C12 C11 178.64(15) . . . . ?
C5 C7 C12 C13 -2.4(2) . . . . ?
C6 N1 C13 C12 2.9(2) . . . . ?
C6 N1 C13 C14 -176.97(15) . . . . ?
C6 N1 B1 F1 59.19(19) . . . . ?
C6 N1 B1 F2 -61.14(19) . . . . ?
C6 N1 B1 O1 179.34(14) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C6 C5 C7 C8 -176.96(15) . . . . ?
C6 C5 C7 C12 2.6(2) . . . . ?
C7 C5 C6 N1 -0.1(2) . . . . ?
C7 C5 C6 C1 179.66(15) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C7 C12 C13 N1 -0.3(2) . . . . ?
C7 C12 C13 C14 179.59(16) . . . . ?
C8 C7 C12 C11 -1.8(2) . . . . ?
C8 C7 C12 C13 177.15(14) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C7 0.4(2) . . . . ?
C10 C11 C12 C13 -178.46(16) . . . . ?
C11 C12 C13 N1 178.61(15) . . . . ?
C11 C12 C13 C14 -1.5(2) . . . . ?
C12 C7 C8 C9 1.9(2) . . . . ?
C12 C13 C14 C15 177.83(15) . . . . ?
C13 N1 C6 C1 177.51(15) . . . . ?
C13 N1 C6 C5 -2.7(2) . . . . ?
C13 N1 B1 F1 -122.19(16) . . . . ?
C13 N1 B1 F2 117.48(16) . . . . ?
C13 N1 B1 O1 -2.0(2) . . . . ?
C13 C14 C15 O1 -2.7(3) . . . . ?
C13 C14 C15 C16 176.71(16) . . . . ?
C14 C15 C16 C17 179.64(17) . . . . ?
C14 C15 C16 C21 -5.2(3) . . . . ?
C15 O1 B1 F1 118.40(18) . . . . ?
C15 O1 B1 F2 -122.24(17) . . . . ?
C15 O1 B1 N1 -3.0(2) . . . . ?
C15 C16 C17 C18 173.30(17) . . . . ?
C15 C16 C21 C20 -172.67(17) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C16 C21 C20 2.7(3) . . . . ?
C17 C18 C19 N2 -176.77(17) . . . . ?
C17 C18 C19 C20 2.7(3) . . . . ?
C18 C19 C20 C21 -2.2(3) . . . . ?
C19 C20 C21 C16 -0.5(3) . . . . ?
C21 C16 C17 C18 -2.1(3) . . . . ?
C22 N2 C19 C18 177.23(18) . . . . ?
C22 N2 C19 C20 -2.2(3) . . . . ?
C23 N2 C19 C18 3.7(3) . . . . ?
C23 N2 C19 C20 -175.76(16) . . . . ?
B1 O1 C15 C14 5.3(3) . . . . ?
B1 O1 C15 C16 -174.09(16) . . . . ?
B1 N1 C6 C1 -3.9(2) . . . . ?
B1 N1 C6 C5 175.88(15) . . . . ?
B1 N1 C13 C12 -175.69(14) . . . . ?
B1 N1 C13 C14 4.4(2) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF/hexane(1:1)'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1011524'
_audit_update_record             
;
2014-07-01 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;
_audit_creation_date             2014-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(Z)-2-(phenanthridin-6-yl)-1-phenylethenol difluoroboron'
_chemical_formula_moiety         'C21 H14 B F2 N O'
_chemical_formula_sum            'C21 H14 B F2 N O'
_chemical_formula_weight         345.14
_chemical_absolute_configuration unk
_chemical_melting_point          400.5-401.7
_chemical_oxdiff_formula         'c10 h10 n2 O8 B1 F5'
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 'x+1/2, -y+1/2, z'
4 '-x+1/2, y+1/2, z+1/2'

_cell_length_a                   30.2538(15)
_cell_length_b                   7.7757(4)
_cell_length_c                   13.4669(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3168.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3680
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5311
_cell_measurement_theta_min      2.9396
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19065
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.95
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0045513000
_diffrn_orient_matrix_UB_12      -0.0504799000
_diffrn_orient_matrix_UB_13      0.0189958000
_diffrn_orient_matrix_UB_21      -0.0192248000
_diffrn_orient_matrix_UB_22      0.0021813000
_diffrn_orient_matrix_UB_23      -0.0521093000
_diffrn_orient_matrix_UB_31      0.0126426000
_diffrn_orient_matrix_UB_32      -0.0148119000
_diffrn_orient_matrix_UB_33      -0.0724079000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2473
_reflns_number_total             3032
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(8)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         3032
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0429P)²+0.1129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0848
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25),
  C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C35(H35), C38(H38),
 C39(H39), C40(H40), C41(H41), C42(H42)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.21984(6) 1.0610(2) 0.31219(16) 0.0618(5) Uani 1 d . . .
F2 F 0.24180(5) 0.7869(2) 0.28731(16) 0.0620(5) Uani 1 d . . .
O1 O 0.18957(7) 0.8475(3) 0.40565(17) 0.0603(6) Uani 1 d . . .
N1 N 0.17011(7) 0.8685(3) 0.22459(18) 0.0372(5) Uani 1 d . . .
C1 C 0.18077(9) 0.9106(3) 0.1255(2) 0.0381(7) Uani 1 d . . .
C2 C 0.22243(10) 0.9786(4) 0.1023(3) 0.0493(8) Uani 1 d . . .
H2 H 0.2428 0.9988 0.1526 0.059 Uiso 1 calc . . R
C3 C 0.23317(11) 1.0154(4) 0.0060(3) 0.0572(9) Uani 1 d . . .
H3 H 0.2611 1.0584 -0.0086 0.069 Uiso 1 calc . . R
C4 C 0.20331(12) 0.9897(4) -0.0697(3) 0.0600(9) Uani 1 d . . .
H4 H 0.2110 1.0154 -0.1349 0.072 Uiso 1 calc . . R
C5 C 0.16242(11) 0.9262(4) -0.0480(3) 0.0533(8) Uani 1 d . . .
H5 H 0.1422 0.9100 -0.0992 0.064 Uiso 1 calc . . R
C6 C 0.15001(9) 0.8845(3) 0.0495(2) 0.0409(7) Uani 1 d . . .
C7 C 0.10733(9) 0.8104(3) 0.0721(2) 0.0406(7) Uani 1 d . . .
C8 C 0.07474(10) 0.7804(4) -0.0007(3) 0.0533(8) Uani 1 d . . .
H8 H 0.0800 0.8142 -0.0659 0.064 Uiso 1 calc . . R
C9 C 0.03569(10) 0.7028(4) 0.0227(3) 0.0582(9) Uani 1 d . . .
H9 H 0.0146 0.6838 -0.0263 0.070 Uiso 1 calc . . R
C10 C 0.02747(10) 0.6523(4) 0.1193(3) 0.0572(9) Uani 1 d . . .
H10 H 0.0010 0.5977 0.1346 0.069 Uiso 1 calc . . R
C11 C 0.05764(9) 0.6814(4) 0.1925(3) 0.0503(8) Uani 1 d . . .
H11 H 0.0515 0.6477 0.2573 0.060 Uiso 1 calc . . R
C12 C 0.09836(9) 0.7627(3) 0.1703(2) 0.0394(7) Uani 1 d . . .
C13 C 0.13081(9) 0.7964(3) 0.2472(2) 0.0369(7) Uani 1 d . . .
C14 C 0.12188(10) 0.7521(4) 0.3477(2) 0.0466(8) Uani 1 d . . .
H14 H 0.0947 0.7025 0.3625 0.056 Uiso 1 calc . . R
C15 C 0.15046(9) 0.7778(3) 0.4222(2) 0.0400(7) Uani 1 d . . .
C16 C 0.14222(10) 0.7322(3) 0.5273(2) 0.0427(7) Uani 1 d . . .
C17 C 0.10242(11) 0.6618(4) 0.5587(3) 0.0545(8) Uani 1 d . . .
H17 H 0.0801 0.6407 0.5127 0.065 Uiso 1 calc . . R
C18 C 0.09567(12) 0.6230(4) 0.6570(3) 0.0638(9) Uani 1 d . . .
H18 H 0.0687 0.5778 0.6772 0.077 Uiso 1 calc . . R
C19 C 0.12857(12) 0.6504(4) 0.7262(3) 0.0622(9) Uani 1 d . . .
H19 H 0.1238 0.6244 0.7927 0.075 Uiso 1 calc . . R
C20 C 0.16840(12) 0.7163(4) 0.6961(3) 0.0603(9) Uani 1 d . . .
H20 H 0.1910 0.7322 0.7421 0.072 Uiso 1 calc . . R
C21 C 0.17512(11) 0.7592(4) 0.5975(3) 0.0505(8) Uani 1 d . . .
H21 H 0.2020 0.8067 0.5780 0.061 Uiso 1 calc . . R
B1 B 0.20649(10) 0.8921(4) 0.3084(3) 0.0422(8) Uani 1 d . . .
F3 F 0.00791(6) 1.3146(2) 0.28108(17) 0.0708(6) Uani 1 d . . .
F4 F 0.02095(7) 1.0324(2) 0.26036(17) 0.0764(6) Uani 1 d . . .
O2 O 0.05969(7) 1.1767(4) 0.37665(18) 0.0706(7) Uani 1 d . . .
N2 N 0.07490(7) 1.2376(3) 0.19695(19) 0.0376(6) Uani 1 d . . .
C22 C 0.06193(9) 1.2392(3) 0.0964(2) 0.0397(7) Uani 1 d . . .
C23 C 0.01940(10) 1.1864(4) 0.0689(3) 0.0499(8) Uani 1 d . . .
H23 H -0.0006 1.1523 0.1176 0.060 Uiso 1 calc . . R
C24 C 0.00698(11) 1.1846(4) -0.0286(3) 0.0572(9) Uani 1 d . . .
H24 H -0.0211 1.1463 -0.0459 0.069 Uiso 1 calc . . R
C25 C 0.03576(12) 1.2391(4) -0.1022(3) 0.0644(10) Uani 1 d . . .
H25 H 0.0270 1.2390 -0.1684 0.077 Uiso 1 calc . . R
C26 C 0.07726(11) 1.2932(4) -0.0764(3) 0.0553(8) Uani 1 d . . .
H26 H 0.0965 1.3302 -0.1259 0.066 Uiso 1 calc . . R
C27 C 0.09149(10) 1.2942(4) 0.0232(2) 0.0421(7) Uani 1 d . . .
C28 C 0.13509(9) 1.3557(3) 0.0514(2) 0.0423(7) Uani 1 d . . .
C29 C 0.16585(10) 1.4185(4) -0.0181(3) 0.0530(8) Uani 1 d . . .
H29 H 0.1590 1.4156 -0.0854 0.064 Uiso 1 calc . . R
C30 C 0.20581(11) 1.4840(4) 0.0123(3) 0.0585(9) Uani 1 d . . .
H30 H 0.2259 1.5252 -0.0343 0.070 Uiso 1 calc . . R
C31 C 0.21604(10) 1.4885(4) 0.1117(3) 0.0549(9) Uani 1 d . . .
H31 H 0.2427 1.5362 0.1322 0.066 Uiso 1 calc . . R
C32 C 0.18756(9) 1.4240(3) 0.1806(3) 0.0497(8) Uani 1 d . . .
H32 H 0.1954 1.4249 0.2473 0.060 Uiso 1 calc . . R
C33 C 0.14628(9) 1.3557(3) 0.1521(2) 0.0403(7) Uani 1 d . . .
C34 C 0.11534(9) 1.2896(3) 0.2249(2) 0.0390(7) Uani 1 d . . .
C35 C 0.12736(10) 1.2801(4) 0.3263(2) 0.0467(8) Uani 1 d . . .
H35 H 0.1555 1.3166 0.3443 0.056 Uiso 1 calc . . R
C36 C 0.10057(9) 1.2219(3) 0.3981(2) 0.0425(7) Uani 1 d . . .
C37 C 0.11313(10) 1.2007(3) 0.5023(2) 0.0426(7) Uani 1 d . . .
C38 C 0.08273(10) 1.1351(4) 0.5700(2) 0.0497(8) Uani 1 d . . .
H38 H 0.0544 1.1060 0.5488 0.060 Uiso 1 calc . . R
C39 C 0.09420(13) 1.1127(4) 0.6683(3) 0.0614(9) Uani 1 d . . .
H39 H 0.0739 1.0661 0.7127 0.074 Uiso 1 calc . . R
C40 C 0.13554(12) 1.1593(4) 0.7004(3) 0.0620(10) Uani 1 d . . .
H40 H 0.1430 1.1458 0.7669 0.074 Uiso 1 calc . . R
C41 C 0.16605(12) 1.2259(4) 0.6348(3) 0.0606(9) Uani 1 d . . .
H41 H 0.1940 1.2574 0.6570 0.073 Uiso 1 calc . . R
C42 C 0.15494(10) 1.2456(4) 0.5366(3) 0.0543(9) Uani 1 d . . .
H42 H 0.1757 1.2895 0.4923 0.065 Uiso 1 calc . . R
B2 B 0.03957(11) 1.1883(4) 0.2804(3) 0.0448(8) Uani 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 1.375(4) . ?
F2 B1 1.375(4) . ?
O1 C15 1.320(3) . ?
O1 B1 1.448(4) . ?
N1 C1 1.411(4) . ?
N1 C13 1.349(3) . ?
N1 B1 1.588(4) . ?
C1 C2 1.402(4) . ?
C1 C6 1.398(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(5) . ?
C6 C7 1.447(4) . ?
C7 C8 1.410(4) . ?
C7 C12 1.400(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.364(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.362(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.417(4) . ?
C12 C13 1.451(4) . ?
C13 C14 1.422(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.340(4) . ?
C15 C16 1.480(4) . ?
C16 C17 1.389(4) . ?
C16 C21 1.389(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(5) . ?
C21 H21 0.9300 . ?
F3 B2 1.371(4) . ?
F4 B2 1.364(4) . ?
O2 C36 1.318(3) . ?
O2 B2 1.435(5) . ?
N2 C22 1.410(4) . ?
N2 C34 1.343(3) . ?
N2 B2 1.598(4) . ?
C22 C23 1.400(4) . ?
C22 C27 1.398(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.367(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.385(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.369(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.409(5) . ?
C27 C28 1.454(4) . ?
C28 C29 1.407(4) . ?
C28 C33 1.398(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.374(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.375(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.362(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.410(4) . ?
C33 C34 1.450(4) . ?
C34 C35 1.415(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.340(4) . ?
C36 C37 1.464(5) . ?
C37 C38 1.392(4) . ?
C37 C42 1.391(4) . ?
C38 H38 0.9300 . ?
C38 C39 1.379(5) . ?
C39 H39 0.9300 . ?
C39 C40 1.372(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.379(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.373(5) . ?
C42 H42 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
C15 O1 B1 124.6(2) . . ?
C1 N1 B1 119.2(2) . . ?
C13 N1 C1 120.8(2) . . ?
C13 N1 B1 119.9(2) . . ?
C2 C1 N1 120.2(3) . . ?
C6 C1 N1 120.4(3) . . ?
C6 C1 C2 119.3(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.8(3) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 C7 119.8(3) . . ?
C5 C6 C7 121.9(3) . . ?
C8 C7 C6 122.9(3) . . ?
C12 C7 C6 118.5(3) . . ?
C12 C7 C8 118.6(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 119.1(3) . . ?
C7 C12 C13 119.7(3) . . ?
C11 C12 C13 121.2(3) . . ?
N1 C13 C12 120.6(3) . . ?
N1 C13 C14 118.9(3) . . ?
C14 C13 C12 120.5(3) . . ?
C13 C14 H14 118.2 . . ?
C15 C14 C13 123.6(3) . . ?
C15 C14 H14 118.2 . . ?
O1 C15 C14 120.9(3) . . ?
O1 C15 C16 114.3(3) . . ?
C14 C15 C16 124.9(3) . . ?
C17 C16 C15 122.1(3) . . ?
C21 C16 C15 119.6(3) . . ?
C21 C16 C17 118.3(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.5(4) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
F1 B1 O1 107.4(3) . . ?
F1 B1 N1 109.9(2) . . ?
F2 B1 F1 110.3(2) . . ?
F2 B1 O1 108.6(3) . . ?
F2 B1 N1 108.8(3) . . ?
O1 B1 N1 111.7(2) . . ?
C36 O2 B2 125.4(3) . . ?
C22 N2 B2 119.5(2) . . ?
C34 N2 C22 121.3(2) . . ?
C34 N2 B2 119.0(3) . . ?
C23 C22 N2 120.4(3) . . ?
C27 C22 N2 120.1(3) . . ?
C27 C22 C23 119.5(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.6 . . ?
C23 C24 C25 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.3(4) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 H26 119.2 . . ?
C25 C26 C27 121.5(3) . . ?
C27 C26 H26 119.2 . . ?
C22 C27 C26 118.3(3) . . ?
C22 C27 C28 119.8(3) . . ?
C26 C27 C28 121.8(3) . . ?
C29 C28 C27 122.7(3) . . ?
C33 C28 C27 118.2(3) . . ?
C33 C28 C29 119.0(3) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.8(3) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.6 . . ?
C32 C31 C30 120.8(3) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 H32 119.5 . . ?
C31 C32 C33 120.9(3) . . ?
C33 C32 H32 119.5 . . ?
C28 C33 C32 118.6(3) . . ?
C28 C33 C34 120.0(3) . . ?
C32 C33 C34 121.4(3) . . ?
N2 C34 C33 120.4(3) . . ?
N2 C34 C35 119.3(3) . . ?
C35 C34 C33 120.4(3) . . ?
C34 C35 H35 118.0 . . ?
C36 C35 C34 123.9(3) . . ?
C36 C35 H35 118.0 . . ?
O2 C36 C35 120.0(3) . . ?
O2 C36 C37 115.0(3) . . ?
C35 C36 C37 124.9(3) . . ?
C38 C37 C36 119.9(3) . . ?
C42 C37 C36 121.7(3) . . ?
C42 C37 C38 118.4(3) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 C37 120.6(3) . . ?
C39 C38 H38 119.7 . . ?
C38 C39 H39 120.1 . . ?
C40 C39 C38 119.9(3) . . ?
C40 C39 H39 120.1 . . ?
C39 C40 H40 119.8 . . ?
C39 C40 C41 120.5(3) . . ?
C41 C40 H40 119.8 . . ?
C40 C41 H41 120.2 . . ?
C42 C41 C40 119.7(3) . . ?
C42 C41 H41 120.2 . . ?
C37 C42 H42 119.5 . . ?
C41 C42 C37 120.9(3) . . ?
C41 C42 H42 119.5 . . ?
F3 B2 O2 109.6(3) . . ?
F3 B2 N2 107.5(2) . . ?
F4 B2 F3 110.5(3) . . ?
F4 B2 O2 107.3(3) . . ?
F4 B2 N2 110.5(3) . . ?
O2 B2 N2 111.5(2) . . ?

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
O1 C15 C16 C17 178.3(3) . . . . ?
O1 C15 C16 C21 -2.0(4) . . . . ?
N1 C1 C2 C3 178.3(3) . . . . ?
N1 C1 C6 C5 -179.1(2) . . . . ?
N1 C1 C6 C7 -1.4(4) . . . . ?
N1 C13 C14 C15 0.0(4) . . . . ?
C1 N1 C13 C12 -0.9(3) . . . . ?
C1 N1 C13 C14 178.4(2) . . . . ?
C1 N1 B1 F1 59.3(3) . . . . ?
C1 N1 B1 F2 -61.6(3) . . . . ?
C1 N1 B1 O1 178.4(2) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
C1 C6 C7 C8 -180.0(3) . . . . ?
C1 C6 C7 C12 -1.5(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C1 C6 C7 178.4(2) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 -177.4(3) . . . . ?
C5 C6 C7 C8 -2.3(4) . . . . ?
C5 C6 C7 C12 176.2(3) . . . . ?
C6 C1 C2 C3 -1.5(4) . . . . ?
C6 C7 C8 C9 176.9(3) . . . . ?
C6 C7 C12 C11 -176.6(2) . . . . ?
C6 C7 C12 C13 3.1(3) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C7 C12 C13 N1 -2.0(3) . . . . ?
C7 C12 C13 C14 178.7(2) . . . . ?
C8 C7 C12 C11 2.0(4) . . . . ?
C8 C7 C12 C13 -178.3(2) . . . . ?
C8 C9 C10 C11 1.1(5) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C7 -0.9(4) . . . . ?
C10 C11 C12 C13 179.4(3) . . . . ?
C11 C12 C13 N1 177.7(2) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
C12 C7 C8 C9 -1.6(4) . . . . ?
C12 C13 C14 C15 179.3(2) . . . . ?
C13 N1 C1 C2 -177.2(2) . . . . ?
C13 N1 C1 C6 2.6(4) . . . . ?
C13 N1 B1 F1 -125.9(3) . . . . ?
C13 N1 B1 F2 113.2(3) . . . . ?
C13 N1 B1 O1 -6.8(3) . . . . ?
C13 C14 C15 O1 -0.1(4) . . . . ?
C13 C14 C15 C16 -179.7(3) . . . . ?
C14 C15 C16 C17 -2.1(4) . . . . ?
C14 C15 C16 C21 177.6(3) . . . . ?
C15 O1 B1 F1 127.6(3) . . . . ?
C15 O1 B1 F2 -113.1(3) . . . . ?
C15 O1 B1 N1 7.0(4) . . . . ?
C15 C16 C17 C18 -179.2(3) . . . . ?
C15 C16 C21 C20 -179.4(3) . . . . ?
C16 C17 C18 C19 -1.2(5) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
C17 C18 C19 C20 -0.3(5) . . . . ?
C18 C19 C20 C21 1.7(5) . . . . ?
C19 C20 C21 C16 -1.7(5) . . . . ?
C21 C16 C17 C18 1.2(4) . . . . ?
B1 O1 C15 C14 -4.0(4) . . . . ?
B1 O1 C15 C16 175.6(2) . . . . ?
B1 N1 C1 C2 -2.4(4) . . . . ?
B1 N1 C1 C6 177.4(2) . . . . ?
B1 N1 C13 C12 -175.6(2) . . . . ?
B1 N1 C13 C14 3.7(3) . . . . ?
O2 C36 C37 C38 0.7(4) . . . . ?
O2 C36 C37 C42 -178.9(3) . . . . ?
N2 C22 C23 C24 -178.7(3) . . . . ?
N2 C22 C27 C26 179.8(2) . . . . ?
N2 C22 C27 C28 -2.3(4) . . . . ?
N2 C34 C35 C36 -0.1(4) . . . . ?
C22 N2 C34 C33 2.5(4) . . . . ?
C22 N2 C34 C35 -177.9(3) . . . . ?
C22 N2 B2 F3 -65.7(3) . . . . ?
C22 N2 B2 F4 54.9(3) . . . . ?
C22 N2 B2 O2 174.2(2) . . . . ?
C22 C23 C24 C25 -1.7(5) . . . . ?
C22 C27 C28 C29 -177.7(3) . . . . ?
C22 C27 C28 C33 0.8(4) . . . . ?
C23 C22 C27 C26 -0.4(4) . . . . ?
C23 C22 C27 C28 177.5(2) . . . . ?
C23 C24 C25 C26 0.9(5) . . . . ?
C24 C25 C26 C27 0.2(5) . . . . ?
C25 C26 C27 C22 -0.5(4) . . . . ?
C25 C26 C27 C28 -178.3(3) . . . . ?
C26 C27 C28 C29 0.1(4) . . . . ?
C26 C27 C28 C33 178.7(3) . . . . ?
C27 C22 C23 C24 1.5(4) . . . . ?
C27 C28 C29 C30 176.5(3) . . . . ?
C27 C28 C33 C32 -176.6(2) . . . . ?
C27 C28 C33 C34 2.2(4) . . . . ?
C28 C29 C30 C31 0.0(5) . . . . ?
C28 C33 C34 N2 -3.9(4) . . . . ?
C28 C33 C34 C35 176.4(3) . . . . ?
C29 C28 C33 C32 2.0(4) . . . . ?
C29 C28 C33 C34 -179.2(2) . . . . ?
C29 C30 C31 C32 2.0(5) . . . . ?
C30 C31 C32 C33 -2.0(5) . . . . ?
C31 C32 C33 C28 -0.1(4) . . . . ?
C31 C32 C33 C34 -178.8(3) . . . . ?
C32 C33 C34 N2 174.8(2) . . . . ?
C32 C33 C34 C35 -4.8(4) . . . . ?
C33 C28 C29 C30 -2.0(4) . . . . ?
C33 C34 C35 C36 179.5(2) . . . . ?
C34 N2 C22 C23 -179.2(2) . . . . ?
C34 N2 C22 C27 0.6(4) . . . . ?
C34 N2 B2 F3 109.1(3) . . . . ?
C34 N2 B2 F4 -130.3(3) . . . . ?
C34 N2 B2 O2 -11.0(4) . . . . ?
C34 C35 C36 O2 -3.2(5) . . . . ?
C34 C35 C36 C37 176.0(3) . . . . ?
C35 C36 C37 C38 -178.5(3) . . . . ?
C35 C36 C37 C42 1.8(4) . . . . ?
C36 O2 B2 F3 -110.5(3) . . . . ?
C36 O2 B2 F4 129.5(3) . . . . ?
C36 O2 B2 N2 8.4(4) . . . . ?
C36 C37 C38 C39 179.3(3) . . . . ?
C36 C37 C42 C41 179.6(3) . . . . ?
C37 C38 C39 C40 1.6(5) . . . . ?
C38 C37 C42 C41 -0.1(5) . . . . ?
C38 C39 C40 C41 -1.0(5) . . . . ?
C39 C40 C41 C42 -0.1(5) . . . . ?
C40 C41 C42 C37 0.6(5) . . . . ?
C42 C37 C38 C39 -1.0(4) . . . . ?
B2 O2 C36 C35 -1.9(5) . . . . ?
B2 O2 C36 C37 178.9(3) . . . . ?
B2 N2 C22 C23 -4.5(4) . . . . ?
B2 N2 C22 C27 175.3(2) . . . . ?
B2 N2 C34 C33 -172.2(2) . . . . ?
B2 N2 C34 C35 7.4(4) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/hexane(1:1)'
_exptl_crystal_preparation       Luminescent
