# Electronic Supplementary Material (ESI) for ChemComm.
# 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_20150506b
_database_code_depnum_ccdc_archive 'CCDC 1405685'
_audit_update_record             
;
2015-06-09 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 B Cl2 F2 N3'
_chemical_formula_weight         512.22

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   19.318(4)
_cell_length_b                   7.0637(14)
_cell_length_c                   19.042(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.007(4)
_cell_angle_gamma                90.00
_cell_volume                     2550.6(9)
_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       culumn
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    0.290
_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     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13799
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.20
_reflns_number_total             4583
_reflns_number_gt                2695
_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)+(0.2000P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4583
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.3108
_refine_ls_wR_factor_gt          0.2616
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
B1 B 0.3190(3) 0.3212(7) 1.0087(3) 0.0520(12) Uani 1 1 d . . .
F1 F 0.38892(13) 0.3737(4) 1.02250(18) 0.0887(11) Uani 1 1 d . . .
F2 F 0.3043(2) 0.2227(4) 1.06658(14) 0.0925(11) Uani 1 1 d . . .
C12 C 0.22072(19) 0.5331(6) 0.93477(19) 0.0432(9) Uani 1 1 d . . .
C8 C 0.3185(2) 0.6608(6) 1.1104(2) 0.0494(10) Uani 1 1 d . . .
H8 H 0.3483 0.5597 1.1260 0.059 Uiso 1 1 calc R . .
C9 C 0.27035(19) 0.6447(6) 1.0418(2) 0.0459(10) Uani 1 1 d . . .
C7 C 0.3218(2) 0.8114(6) 1.1513(2) 0.0481(10) Uani 1 1 d . . .
H7 H 0.2899 0.9076 1.1349 0.058 Uiso 1 1 calc R . .
C6 C 0.4205(2) 0.7200(7) 1.2506(2) 0.0580(12) Uani 1 1 d . . .
H6 H 0.4259 0.6061 1.2277 0.070 Uiso 1 1 calc R . .
C10 C 0.2187(2) 0.7744(6) 1.0108(2) 0.0503(10) Uani 1 1 d . . .
H10 H 0.2077 0.8867 1.0316 0.060 Uiso 1 1 calc R . .
C5 C 0.3694(2) 0.8466(7) 1.2195(2) 0.0530(11) Uani 1 1 d . . .
C11 C 0.1872(2) 0.7087(6) 0.94473(19) 0.0466(10) Uani 1 1 d . . .
C13 C 0.1285(2) 0.8074(7) 0.8954(2) 0.0596(12) Uani 1 1 d . . .
H13A H 0.0878 0.7265 0.8861 0.089 Uiso 1 1 calc R . .
H13B H 0.1432 0.8365 0.8513 0.089 Uiso 1 1 calc R . .
H13C H 0.1168 0.9224 0.9174 0.089 Uiso 1 1 calc R . .
C1 C 0.4645(2) 0.7611(9) 1.3160(2) 0.0692(15) Uani 1 1 d . . .
C4 C 0.3634(3) 1.0174(8) 1.2544(3) 0.0672(13) Uani 1 1 d . . .
H4 H 0.3300 1.1062 1.2341 0.081 Uiso 1 1 calc R . .
C2 C 0.4564(3) 0.9314(9) 1.3487(3) 0.0776(16) Uani 1 1 d . . .
H2 H 0.4858 0.9608 1.3919 0.093 Uiso 1 1 calc R . .
C3 C 0.4073(3) 1.0549(10) 1.3192(3) 0.0837(17) Uani 1 1 d . . .
H3 H 0.4023 1.1683 1.3426 0.100 Uiso 1 1 calc R . .
N3 N 0.30292(16) 0.2008(5) 0.94100(17) 0.0452(8) Uani 1 1 d . . .
C16 C 0.15791(19) 0.4473(6) 0.8124(2) 0.0456(9) Uani 1 1 d . . .
C14 C 0.21198(18) 0.4056(6) 0.87736(19) 0.0438(10) Uani 1 1 d . . .
C15 C 0.25217(19) 0.2437(6) 0.87922(19) 0.0433(9) Uani 1 1 d . . .
C21 C 0.1756(2) 0.5554(6) 0.7580(2) 0.0528(10) Uani 1 1 d . . .
H21 H 0.2210 0.6041 0.7625 0.063 Uiso 1 1 calc R . .
C20 C 0.1263(3) 0.5908(7) 0.6976(2) 0.0630(12) Uani 1 1 d . . .
H20 H 0.1382 0.6635 0.6610 0.076 Uiso 1 1 calc R . .
C19 C 0.0594(3) 0.5195(8) 0.6909(3) 0.0689(14) Uani 1 1 d . . .
H19 H 0.0262 0.5436 0.6496 0.083 Uiso 1 1 calc R . .
C17 C 0.0908(2) 0.3779(7) 0.8052(2) 0.0604(12) Uani 1 1 d . . .
H17 H 0.0783 0.3057 0.8416 0.072 Uiso 1 1 calc R . .
C18 C 0.0414(2) 0.4149(8) 0.7436(3) 0.0692(14) Uani 1 1 d . . .
H18 H -0.0041 0.3673 0.7388 0.083 Uiso 1 1 calc R . .
C24 C 0.3350(2) 0.0387(6) 0.9278(2) 0.0512(10) Uani 1 1 d . . .
C22 C 0.2557(2) 0.0999(6) 0.8283(2) 0.0499(10) Uani 1 1 d . . .
C25 C 0.2144(3) 0.0793(7) 0.7527(2) 0.0628(12) Uani 1 1 d . . .
H25A H 0.2346 -0.0201 0.7288 0.094 Uiso 1 1 calc R . .
H25B H 0.2161 0.1961 0.7273 0.094 Uiso 1 1 calc R . .
H25C H 0.1662 0.0487 0.7541 0.094 Uiso 1 1 calc R . .
C26 C 0.3932(2) -0.0514(7) 0.9791(3) 0.0655(13) Uani 1 1 d . . .
H26A H 0.4351 0.0239 0.9829 0.098 Uiso 1 1 calc R . .
H26B H 0.4019 -0.1758 0.9624 0.098 Uiso 1 1 calc R . .
H26C H 0.3802 -0.0607 1.0252 0.098 Uiso 1 1 calc R . .
C23 C 0.3064(2) -0.0253(7) 0.8597(2) 0.0556(11) Uani 1 1 d . . .
H23 H 0.3195 -0.1353 0.8387 0.067 Uiso 1 1 calc R . .
N2 N 0.27160(15) 0.4984(5) 0.99632(16) 0.0422(8) Uani 1 1 d . . .
N1 N 0.5131(3) 0.6318(9) 1.3475(3) 0.1043(19) Uani 1 1 d . . .
H1A H 0.5392 0.6562 1.3883 0.125 Uiso 1 1 calc R . .
H1B H 0.5175 0.5259 1.3266 0.125 Uiso 1 1 calc R . .
Cl1 Cl 0.05749(16) 0.4763(4) 0.10337(15) 0.1588(11) Uani 1 1 d . . .
Cl2 Cl 0.0720(2) 0.1740(4) 0.00904(14) 0.1869(14) Uani 1 1 d . . .
C27 C 0.1121(5) 0.3563(18) 0.0596(5) 0.166(4) Uani 1 1 d . . .
H27A H 0.1513 0.3068 0.0943 0.200 Uiso 1 1 calc R . .
H27B H 0.1311 0.4436 0.0288 0.200 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
B1 F1 1.377(6) . ?
B1 F2 1.379(6) . ?
B1 N3 1.525(6) . ?
B1 N2 1.542(6) . ?
C12 N2 1.400(4) . ?
C12 C14 1.401(6) . ?
C12 C11 1.429(6) . ?
C8 C7 1.313(6) . ?
C8 C9 1.456(5) . ?
C9 N2 1.351(5) . ?
C9 C10 1.399(6) . ?
C7 C5 1.461(5) . ?
C6 C5 1.380(6) . ?
C6 C1 1.398(6) . ?
C10 C11 1.370(5) . ?
C5 C4 1.393(7) . ?
C11 C13 1.498(5) . ?
C1 N1 1.364(7) . ?
C1 C2 1.376(8) . ?
C4 C3 1.382(7) . ?
C2 C3 1.332(8) . ?
N3 C24 1.348(5) . ?
N3 C15 1.413(4) . ?
C16 C17 1.367(6) . ?
C16 C21 1.381(6) . ?
C16 C14 1.488(5) . ?
C14 C15 1.379(6) . ?
C15 C22 1.415(6) . ?
C21 C20 1.370(6) . ?
C20 C19 1.369(7) . ?
C19 C18 1.345(8) . ?
C17 C18 1.388(6) . ?
C24 C23 1.385(6) . ?
C24 C26 1.483(6) . ?
C22 C23 1.370(6) . ?
C22 C25 1.514(6) . ?
Cl1 C27 1.692(12) . ?
Cl2 C27 1.703(11) . ?

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
F1 B1 F2 109.1(4) . . ?
F1 B1 N3 110.2(4) . . ?
F2 B1 N3 110.8(4) . . ?
F1 B1 N2 110.1(4) . . ?
F2 B1 N2 109.0(4) . . ?
N3 B1 N2 107.7(3) . . ?
N2 C12 C14 120.1(4) . . ?
N2 C12 C11 107.7(3) . . ?
C14 C12 C11 132.1(3) . . ?
C7 C8 C9 123.1(4) . . ?
N2 C9 C10 109.2(3) . . ?
N2 C9 C8 123.2(4) . . ?
C10 C9 C8 127.5(4) . . ?
C8 C7 C5 128.0(4) . . ?
C5 C6 C1 120.8(5) . . ?
C11 C10 C9 108.8(4) . . ?
C6 C5 C4 118.3(4) . . ?
C6 C5 C7 123.3(4) . . ?
C4 C5 C7 118.4(4) . . ?
C10 C11 C12 106.4(3) . . ?
C10 C11 C13 124.7(4) . . ?
C12 C11 C13 129.0(4) . . ?
N1 C1 C2 120.9(5) . . ?
N1 C1 C6 120.2(5) . . ?
C2 C1 C6 118.8(5) . . ?
C3 C4 C5 120.0(5) . . ?
C3 C2 C1 121.0(5) . . ?
C2 C3 C4 121.1(5) . . ?
C24 N3 C15 107.4(3) . . ?
C24 N3 B1 127.1(3) . . ?
C15 N3 B1 125.5(3) . . ?
C17 C16 C21 119.2(4) . . ?
C17 C16 C14 121.0(4) . . ?
C21 C16 C14 119.8(3) . . ?
C15 C14 C12 122.0(3) . . ?
C15 C14 C16 119.2(3) . . ?
C12 C14 C16 118.8(3) . . ?
C14 C15 N3 119.8(3) . . ?
C14 C15 C22 132.7(3) . . ?
N3 C15 C22 107.4(3) . . ?
C20 C21 C16 119.9(4) . . ?
C19 C20 C21 120.3(5) . . ?
C18 C19 C20 120.4(4) . . ?
C16 C17 C18 120.2(4) . . ?
C19 C18 C17 120.0(4) . . ?
N3 C24 C23 109.6(4) . . ?
N3 C24 C26 124.0(4) . . ?
C23 C24 C26 126.3(4) . . ?
C23 C22 C15 106.8(3) . . ?
C23 C22 C25 123.8(4) . . ?
C15 C22 C25 129.4(4) . . ?
C22 C23 C24 108.8(4) . . ?
C9 N2 C12 107.9(3) . . ?
C9 N2 B1 127.3(3) . . ?
C12 N2 B1 124.8(3) . . ?
Cl1 C27 Cl2 113.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.085
