# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_dk_05_52_0m
_database_code_depnum_ccdc_archive 'CCDC 980654'
_audit_update_record             
;
2014-01-08 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H25 B F2 N5 O8 S'
_chemical_formula_weight         676.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   17.4761(5)
_cell_length_b                   8.0976(2)
_cell_length_c                   22.1564(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.7150(10)
_cell_angle_gamma                90.00
_cell_volume                     2912.95(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(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    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1396
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            18631
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         6.13
_diffrn_reflns_theta_max         64.98
_reflns_number_total             4680
_reflns_number_gt                4530
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0531P)²+2.0606P] 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         4680
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
S1 S 0.34149(3) 0.75906(6) 0.05750(2) 0.02940(16) Uani 1 1 d . . .
F1 F 0.44789(6) 0.05827(13) 0.23050(5) 0.0304(3) Uani 1 1 d . . .
F2 F 0.50234(6) 0.31263(13) 0.26247(5) 0.0297(3) Uani 1 1 d . . .
O1 O 0.26122(8) 0.66668(16) 0.05685(6) 0.0298(3) Uani 1 1 d . . .
O2 O 0.62276(10) 0.5789(2) 0.34836(7) 0.0475(4) Uani 1 1 d . . .
O3 O 0.51865(11) 0.6323(3) 0.37552(7) 0.0640(6) Uani 1 1 d . . .
O4 O 0.58637(11) 0.6198(3) 0.11694(8) 0.0604(5) Uani 1 1 d . . .
O5 O 0.52101(10) 0.8492(2) 0.08325(8) 0.0470(4) Uani 1 1 d . . .
O6 O 0.76184(9) 0.2340(2) 0.24757(8) 0.0454(4) Uani 1 1 d . . .
O7 O 0.32297(10) 0.92916(18) 0.05052(8) 0.0483(4) Uani 1 1 d . . .
O8 O 0.37253(9) 0.67666(19) 0.01475(6) 0.0371(3) Uani 1 1 d . . .
N1 N 0.35561(9) 0.29422(19) 0.20591(7) 0.0252(3) Uani 1 1 d . . .
N2 N 0.55081(12) 0.6202(2) 0.33554(8) 0.0405(4) Uani 1 1 d . . .
N3 N 0.53551(10) 0.7245(2) 0.11591(8) 0.0350(4) Uani 1 1 d . . .
N4 N 0.45410(9) 0.24394(18) 0.14753(7) 0.0236(3) Uani 1 1 d . . .
N5 N 0.59584(10) 0.1674(2) 0.16743(8) 0.0336(4) Uani 1 1 d . . .
C1 C 0.43871(17) 0.3005(5) 0.45973(11) 0.0632(9) Uani 1 1 d . . .
H1 H 0.4634 0.2951 0.5048 0.076 Uiso 1 1 calc R . .
C2 C 0.45583(14) 0.1824(4) 0.42201(11) 0.0531(7) Uani 1 1 d . . .
H2 H 0.4914 0.0961 0.4418 0.064 Uiso 1 1 calc R . .
C3 C 0.42057(13) 0.1906(3) 0.35452(10) 0.0404(5) Uani 1 1 d . . .
H3A H 0.4331 0.1104 0.3295 0.049 Uiso 1 1 calc R . .
C4 C 0.36701(12) 0.3174(3) 0.32448(10) 0.0346(5) Uani 1 1 d . . .
C5 C 0.32416(12) 0.3339(2) 0.25318(9) 0.0302(4) Uani 1 1 d . . .
C6 C 0.29503(11) 0.3357(2) 0.14635(9) 0.0265(4) Uani 1 1 d . . .
C7 C 0.31200(11) 0.3303(2) 0.08857(9) 0.0252(4) Uani 1 1 d . . .
C8 C 0.24717(11) 0.3785(2) 0.02509(9) 0.0262(4) Uani 1 1 d . . .
C9 C 0.22533(11) 0.5415(2) 0.00955(9) 0.0266(4) Uani 1 1 d . . .
C10 C 0.40582(12) 0.7217(2) 0.13985(9) 0.0264(4) Uani 1 1 d . . .
C11 C 0.49098(12) 0.7016(2) 0.16003(9) 0.0279(4) Uani 1 1 d . . .
C12 C 0.53934(12) 0.6667(2) 0.22384(9) 0.0301(4) Uani 1 1 d . . .
H12 H 0.5957 0.6492 0.2367 0.036 Uiso 1 1 calc R . .
C13 C 0.50026(12) 0.6591(2) 0.26754(9) 0.0307(4) Uani 1 1 d . . .
C14 C 0.36920(12) 0.7114(2) 0.18555(10) 0.0309(4) Uani 1 1 d . . .
H14 H 0.3125 0.7240 0.1727 0.037 Uiso 1 1 calc R . .
C15 C 0.41689(13) 0.6823(2) 0.25041(10) 0.0329(4) Uani 1 1 d . . .
H15 H 0.3930 0.6785 0.2816 0.039 Uiso 1 1 calc R . .
C16 C 0.16813(11) 0.5916(3) -0.04931(9) 0.0323(4) Uani 1 1 d . . .
H16 H 0.1551 0.7028 -0.0576 0.039 Uiso 1 1 calc R . .
C17 C 0.13056(12) 0.4732(3) -0.09570(9) 0.0364(5) Uani 1 1 d . . .
H17 H 0.0923 0.5043 -0.1360 0.044 Uiso 1 1 calc R . .
C18 C 0.15003(12) 0.3082(3) -0.08207(10) 0.0370(5) Uani 1 1 d . . .
H18 H 0.1240 0.2284 -0.1131 0.044 Uiso 1 1 calc R . .
C19 C 0.20807(12) 0.2610(2) -0.02256(10) 0.0318(4) Uani 1 1 d . . .
H19 H 0.2211 0.1499 -0.0143 0.038 Uiso 1 1 calc R . .
C20 C 0.38773(11) 0.2892(2) 0.08981(8) 0.0243(4) Uani 1 1 d . . .
C21 C 0.51974(11) 0.2157(2) 0.12998(9) 0.0266(4) Uani 1 1 d . . .
C22 C 0.62814(12) 0.1207(3) 0.23575(9) 0.0344(5) Uani 1 1 d . . .
H22A H 0.6474 0.0073 0.2402 0.041 Uiso 1 1 calc R . .
H22B H 0.5849 0.1283 0.2532 0.041 Uiso 1 1 calc R . .
C23 C 0.69847(14) 0.2341(3) 0.27321(11) 0.0440(5) Uani 1 1 d . . .
H23A H 0.6776 0.3456 0.2719 0.053 Uiso 1 1 calc R . .
H23B H 0.7212 0.1994 0.3183 0.053 Uiso 1 1 calc R . .
C24 C 0.72932(14) 0.2813(4) 0.18145(13) 0.0518(6) Uani 1 1 d . . .
H24A H 0.7731 0.2825 0.1645 0.062 Uiso 1 1 calc R . .
H24B H 0.7070 0.3921 0.1778 0.062 Uiso 1 1 calc R . .
C25 C 0.66268(13) 0.1644(4) 0.14189(11) 0.0513(7) Uani 1 1 d . . .
H25A H 0.6417 0.1979 0.0966 0.062 Uiso 1 1 calc R . .
H25B H 0.6847 0.0535 0.1447 0.062 Uiso 1 1 calc R . .
C26 C 0.49604(12) 0.2445(3) 0.06105(9) 0.0331(5) Uani 1 1 d . . .
H26 H 0.5300 0.2350 0.0374 0.040 Uiso 1 1 calc R . .
C27 C 0.41636(12) 0.2874(2) 0.03742(9) 0.0303(4) Uani 1 1 d . . .
H27 H 0.3851 0.3118 -0.0057 0.036 Uiso 1 1 calc R . .
C28 C 0.24541(12) 0.3964(3) 0.22278(10) 0.0346(5) Uani 1 1 d . . .
H28 H 0.2109 0.4325 0.2435 0.042 Uiso 1 1 calc R . .
C29 C 0.22665(12) 0.3961(3) 0.15619(10) 0.0333(4) Uani 1 1 d . . .
H29 H 0.1774 0.4300 0.1243 0.040 Uiso 1 1 calc R . .
C30 C 0.38492(18) 0.4268(4) 0.43073(13) 0.0614(8) Uani 1 1 d . . .
H30 H 0.3728 0.5063 0.4562 0.074 Uiso 1 1 calc R . .
C31 C 0.34874(15) 0.4353(3) 0.36346(11) 0.0457(6) Uani 1 1 d . . .
H31 H 0.3120 0.5201 0.3441 0.055 Uiso 1 1 calc R . .
B1 B 0.44127(13) 0.2255(3) 0.21362(10) 0.0239(4) 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
S1 O7 1.4103(16) . ?
S1 O8 1.4201(15) . ?
S1 O1 1.5852(13) . ?
S1 C10 1.7796(19) . ?
F1 B1 1.398(2) . ?
F2 B1 1.398(2) . ?
O1 C9 1.426(2) . ?
O2 N2 1.229(3) . ?
O3 N2 1.216(2) . ?
O4 N3 1.222(2) . ?
O5 N3 1.213(2) . ?
O6 C24 1.414(3) . ?
O6 C23 1.419(3) . ?
N1 C5 1.389(2) . ?
N1 C6 1.393(2) . ?
N1 B1 1.546(3) . ?
N2 C13 1.471(3) . ?
N3 C11 1.469(3) . ?
N4 C21 1.360(2) . ?
N4 C20 1.420(2) . ?
N4 B1 1.568(2) . ?
N5 C21 1.339(2) . ?
N5 C22 1.457(2) . ?
N5 C25 1.475(3) . ?
C1 C2 1.373(4) . ?
C1 C30 1.377(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3A 0.9300 . ?
C4 C31 1.401(3) . ?
C4 C5 1.483(3) . ?
C5 C28 1.385(3) . ?
C6 C29 1.381(3) . ?
C6 C7 1.418(3) . ?
C7 C20 1.355(3) . ?
C7 C8 1.495(2) . ?
C8 C9 1.382(3) . ?
C8 C19 1.397(3) . ?
C9 C16 1.378(3) . ?
C10 C14 1.386(3) . ?
C10 C11 1.396(3) . ?
C11 C12 1.382(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C15 1.376(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C27 1.424(3) . ?
C21 C26 1.446(3) . ?
C22 C23 1.513(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.505(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.339(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.388(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C31 1.389(4) . ?
C30 H30 0.9300 . ?
C31 H31 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
O7 S1 O8 120.97(10) . . ?
O7 S1 O1 107.06(9) . . ?
O8 S1 O1 109.11(8) . . ?
O7 S1 C10 108.12(9) . . ?
O8 S1 C10 110.58(9) . . ?
O1 S1 C10 98.64(8) . . ?
C9 O1 S1 119.29(11) . . ?
C24 O6 C23 109.91(17) . . ?
C5 N1 C6 106.53(15) . . ?
C5 N1 B1 129.59(15) . . ?
C6 N1 B1 123.83(15) . . ?
O3 N2 O2 124.26(18) . . ?
O3 N2 C13 117.68(19) . . ?
O2 N2 C13 118.06(18) . . ?
O5 N3 O4 125.33(19) . . ?
O5 N3 C11 117.17(17) . . ?
O4 N3 C11 117.44(18) . . ?
C21 N4 C20 106.27(15) . . ?
C21 N4 B1 132.69(15) . . ?
C20 N4 B1 120.93(15) . . ?
C21 N5 C22 129.35(16) . . ?
C21 N5 C25 120.87(17) . . ?
C22 N5 C25 109.71(15) . . ?
C2 C1 C30 119.9(2) . . ?
C2 C1 H1 120.1 . . ?
C30 C1 H1 120.1 . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C31 118.5(2) . . ?
C3 C4 C5 124.38(19) . . ?
C31 C4 C5 117.1(2) . . ?
C28 C5 N1 108.49(17) . . ?
C28 C5 C4 124.78(18) . . ?
N1 C5 C4 126.71(17) . . ?
C29 C6 N1 109.53(16) . . ?
C29 C6 C7 129.48(17) . . ?
N1 C6 C7 120.55(16) . . ?
C20 C7 C6 121.23(16) . . ?
C20 C7 C8 118.53(16) . . ?
C6 C7 C8 120.17(16) . . ?
C9 C8 C19 116.70(17) . . ?
C9 C8 C7 121.80(17) . . ?
C19 C8 C7 121.45(17) . . ?
C16 C9 C8 123.61(18) . . ?
C16 C9 O1 117.01(17) . . ?
C8 C9 O1 119.35(16) . . ?
C14 C10 C11 119.00(17) . . ?
C14 C10 S1 118.15(15) . . ?
C11 C10 S1 122.85(14) . . ?
C12 C11 C10 121.84(18) . . ?
C12 C11 N3 115.63(16) . . ?
C10 C11 N3 122.46(17) . . ?
C13 C12 C11 116.99(18) . . ?
C13 C12 H12 121.5 . . ?
C11 C12 H12 121.5 . . ?
C12 C13 C15 123.37(18) . . ?
C12 C13 N2 117.61(18) . . ?
C15 C13 N2 119.00(18) . . ?
C10 C14 C15 120.23(18) . . ?
C10 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C13 C15 C14 118.51(18) . . ?
C13 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C9 C16 C17 118.59(19) . . ?
C9 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C16 C17 C18 119.80(18) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.52(19) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C8 120.78(19) . . ?
C18 C19 H19 119.6 . . ?
C8 C19 H19 119.6 . . ?
C7 C20 N4 123.20(16) . . ?
C7 C20 C27 128.40(17) . . ?
N4 C20 C27 108.37(15) . . ?
N5 C21 N4 128.41(17) . . ?
N5 C21 C26 122.17(17) . . ?
N4 C21 C26 109.42(16) . . ?
N5 C22 C23 109.63(17) . . ?
N5 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
N5 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
O6 C23 C22 112.08(18) . . ?
O6 C23 H23A 109.2 . . ?
C22 C23 H23A 109.2 . . ?
O6 C23 H23B 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
O6 C24 C25 111.2(2) . . ?
O6 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
O6 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
N5 C25 C24 108.6(2) . . ?
N5 C25 H25A 110.0 . . ?
C24 C25 H25A 110.0 . . ?
N5 C25 H25B 110.0 . . ?
C24 C25 H25B 110.0 . . ?
H25A C25 H25B 108.4 . . ?
C27 C26 C21 107.75(17) . . ?
C27 C26 H26 126.1 . . ?
C21 C26 H26 126.1 . . ?
C26 C27 C20 108.19(17) . . ?
C26 C27 H27 125.9 . . ?
C20 C27 H27 125.9 . . ?
C5 C28 C29 108.53(17) . . ?
C5 C28 H28 125.7 . . ?
C29 C28 H28 125.7 . . ?
C6 C29 C28 106.90(17) . . ?
C6 C29 H29 126.6 . . ?
C28 C29 H29 126.6 . . ?
C1 C30 C31 119.9(3) . . ?
C1 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 C4 120.7(3) . . ?
C30 C31 H31 119.6 . . ?
C4 C31 H31 119.6 . . ?
F2 B1 F1 108.53(15) . . ?
F2 B1 N1 109.54(15) . . ?
F1 B1 N1 111.04(15) . . ?
F2 B1 N4 110.07(15) . . ?
F1 B1 N4 108.41(15) . . ?
N1 B1 N4 109.25(14) . . ?

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        64.98
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_dk
_database_code_depnum_ccdc_archive 'CCDC 980655'
_audit_update_record             
;
2014-01-08 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 B Br Cl2 F2 N3 O2'
_chemical_formula_weight         518.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   14.8291(4)
_cell_length_b                   12.6719(3)
_cell_length_c                   21.3493(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4011.81(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(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    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2080
_exptl_absorpt_coefficient_mu    5.616
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            23515
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         5.04
_diffrn_reflns_theta_max         72.33
_reflns_number_total             3846
_reflns_number_gt                3706
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1000P)²+0.1301P] 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         3846
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2562
_refine_ls_R_factor_gt           0.2522
_refine_ls_wR_factor_ref         0.6287
_refine_ls_wR_factor_gt          0.6214
_refine_ls_goodness_of_fit_ref   6.502
_refine_ls_restrained_S_all      6.502
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.12989(10) -0.03070(13) 0.45621(8) 0.0238(9) Uani 1 1 d . . .
C5 C 0.3241(9) 0.0467(10) 0.7572(8) 0.021(3) Uani 1 1 d . . .
C4 C 0.3177(9) 0.1292(11) 0.7134(5) 0.016(3) Uani 1 1 d . . .
C6 C 0.3088(10) 0.0690(16) 0.8200(7) 0.033(4) Uani 1 1 d . . .
H6 H 0.3103 0.0129 0.8481 0.040 Uiso 1 1 calc R . .
C3 C 0.3018(11) 0.2357(15) 0.7353(7) 0.028(4) Uani 1 1 d . . .
H3 H 0.2986 0.2924 0.7078 0.034 Uiso 1 1 calc R . .
C2 C 0.2911(10) 0.2494(14) 0.8022(7) 0.027(4) Uani 1 1 d . . .
H2 H 0.2834 0.3173 0.8178 0.032 Uiso 1 1 calc R . .
C1 C 0.2919(10) 0.1670(16) 0.8435(7) 0.033(4) Uani 1 1 d . . .
H1 H 0.2812 0.1774 0.8859 0.039 Uiso 1 1 calc R . .
N3 N 0.2421(8) 0.0532(9) 0.5522(6) 0.016(3) Uani 1 1 d . . .
C8 C 0.2477(9) 0.0609(10) 0.6158(7) 0.018(3) Uani 1 1 d . . .
C10 C 0.3890(9) 0.1581(10) 0.6087(7) 0.014(3) Uani 1 1 d . . .
C11 C 0.4705(8) 0.2080(10) 0.6297(6) 0.012(2) Uani 1 1 d . . .
H11 H 0.4871 0.2198 0.6711 0.014 Uiso 1 1 calc R . .
C7 C 0.3191(10) 0.1145(10) 0.6459(6) 0.016(3) Uani 1 1 d . . .
C12 C 0.5189(10) 0.2346(10) 0.5783(7) 0.023(3) Uani 1 1 d . . .
H12 H 0.5749 0.2676 0.5778 0.027 Uiso 1 1 calc R . .
C17 C 0.5866(9) 0.2567(12) 0.4499(6) 0.016(3) Uani 1 1 d . . .
H17A H 0.6180 0.2739 0.4884 0.019 Uiso 1 1 calc R . .
H17B H 0.5829 0.3199 0.4244 0.019 Uiso 1 1 calc R . .
C13 C 0.4665(9) 0.2017(9) 0.5239(6) 0.011(2) Uani 1 1 d . . .
C14 C 0.4489(8) 0.1911(11) 0.4060(6) 0.015(3) Uani 1 1 d . . .
H14A H 0.4474 0.2525 0.3789 0.018 Uiso 1 1 calc R . .
H14B H 0.3874 0.1689 0.4141 0.018 Uiso 1 1 calc R . .
C16 C 0.6347(10) 0.1750(15) 0.4164(10) 0.033(4) Uani 1 1 d . . .
H16A H 0.6944 0.2012 0.4062 0.039 Uiso 1 1 calc R . .
H16B H 0.6423 0.1150 0.4441 0.039 Uiso 1 1 calc R . .
C15 C 0.5030(14) 0.100(3) 0.3742(13) 0.102(14) Uani 1 1 d . . .
H15A H 0.5067 0.0396 0.4020 0.122 Uiso 1 1 calc R . .
H15B H 0.4734 0.0782 0.3358 0.122 Uiso 1 1 calc R . .
N1 N 0.4938(8) 0.2166(9) 0.4643(6) 0.016(2) Uani 1 1 d . . .
O1 O 0.5929(8) 0.1398(13) 0.3606(8) 0.061(5) Uani 1 1 d . . .
N2 N 0.3873(7) 0.1549(8) 0.5432(5) 0.008(2) Uani 1 1 d . . .
B1 B 0.3104(9) 0.1001(11) 0.5056(7) 0.012(3) Uani 1 1 d . . .
F2 F 0.3458(6) 0.0235(6) 0.4669(4) 0.0172(18) Uani 1 1 d . . .
F1 F 0.2673(5) 0.1775(7) 0.4675(4) 0.0178(18) Uani 1 1 d . . .
O2 O 0.3409(11) -0.0509(9) 0.7422(7) 0.045(4) Uani 1 1 d . . .
H2A H 0.3741 -0.0524 0.7115 0.067 Uiso 1 1 calc R . .
C19 C 0.1272(9) -0.0342(11) 0.5923(8) 0.018(3) Uani 1 1 d . . .
H19 H 0.0744 -0.0736 0.5946 0.022 Uiso 1 1 calc R . .
C18 C 0.1711(10) -0.0048(12) 0.5393(7) 0.018(3) Uani 1 1 d . . .
C20 C 0.1747(9) 0.0046(12) 0.6406(8) 0.022(3) Uani 1 1 d . . .
H20 H 0.1615 -0.0043 0.6828 0.026 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
Br1 C18 1.905(16) . ?
C5 O2 1.302(17) . ?
C5 C4 1.41(2) . ?
C5 C6 1.39(2) . ?
C4 C3 1.45(2) . ?
C4 C7 1.455(16) . ?
C6 C1 1.36(3) . ?
C3 C2 1.447(19) . ?
C2 C1 1.37(3) . ?
N3 C18 1.31(2) . ?
N3 C8 1.364(19) . ?
N3 B1 1.538(18) . ?
C8 C20 1.40(2) . ?
C8 C7 1.41(2) . ?
C10 C7 1.417(19) . ?
C10 N2 1.400(16) . ?
C10 C11 1.436(18) . ?
C11 C12 1.35(2) . ?
C12 C13 1.457(18) . ?
C17 N1 1.499(17) . ?
C17 C16 1.45(2) . ?
C13 N1 1.349(17) . ?
C13 N2 1.380(16) . ?
C14 N1 1.447(17) . ?
C14 C15 1.56(3) . ?
C16 O1 1.42(2) . ?
C15 O1 1.45(2) . ?
N2 B1 1.557(16) . ?
B1 F2 1.380(16) . ?
B1 F1 1.425(15) . ?
C19 C18 1.36(2) . ?
C19 C20 1.34(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C5 C4 123.8(15) . . ?
O2 C5 C6 117.5(16) . . ?
C4 C5 C6 118.7(13) . . ?
C5 C4 C3 119.3(12) . . ?
C5 C4 C7 124.3(12) . . ?
C3 C4 C7 116.3(12) . . ?
C1 C6 C5 124.7(15) . . ?
C4 C3 C2 116.7(16) . . ?
C1 C2 C3 122.9(16) . . ?
C6 C1 C2 117.5(13) . . ?
C18 N3 C8 107.3(12) . . ?
C18 N3 B1 127.5(12) . . ?
C8 N3 B1 125.2(12) . . ?
N3 C8 C20 107.0(13) . . ?
N3 C8 C7 122.2(13) . . ?
C20 C8 C7 130.7(14) . . ?
C7 C10 N2 122.4(12) . . ?
C7 C10 C11 127.8(12) . . ?
N2 C10 C11 109.8(11) . . ?
C12 C11 C10 107.6(12) . . ?
C10 C7 C8 118.7(12) . . ?
C10 C7 C4 121.1(12) . . ?
C8 C7 C4 120.1(12) . . ?
C11 C12 C13 107.0(12) . . ?
N1 C17 C16 108.2(12) . . ?
N1 C13 N2 126.6(11) . . ?
N1 C13 C12 123.5(12) . . ?
N2 C13 C12 109.8(12) . . ?
N1 C14 C15 107.6(14) . . ?
O1 C16 C17 115.2(13) . . ?
O1 C15 C14 108(2) . . ?
C13 N1 C17 121.1(11) . . ?
C13 N1 C14 129.9(12) . . ?
C17 N1 C14 108.7(10) . . ?
C16 O1 C15 110.0(15) . . ?
C13 N2 C10 105.7(10) . . ?
C13 N2 B1 131.5(10) . . ?
C10 N2 B1 122.7(10) . . ?
F2 B1 F1 108.2(11) . . ?
F2 B1 N3 111.4(11) . . ?
F1 B1 N3 109.9(9) . . ?
F2 B1 N2 110.1(10) . . ?
F1 B1 N2 108.4(10) . . ?
N3 B1 N2 108.8(11) . . ?
C18 C19 C20 106.8(13) . . ?
N3 C18 C19 111.4(14) . . ?
N3 C18 Br1 123.3(11) . . ?
C19 C18 Br1 125.1(12) . . ?
C8 C20 C19 107.5(14) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        72.33
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         17.079
_refine_diff_density_min         -1.964
_refine_diff_density_rms         0.602
