# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_h027
_database_code_depnum_ccdc_archive 'CCDC 1490358'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_DIFF003_h027                
;
PROBLEM: _diffrn_measurement_device_type is missing
RESPONSE: SAMRT APEX BRUKER
;
_vrf_PLAT183_h027                
;
PROBLEM: Missing _cell_measurement_reflns_used value ....     Please Do !
RESPONSE: 40
;
_vrf_PLAT053_h027                
;
PROBLEM: Minimum Crystal Dimension Missing (or Error) ...     Please Check
RESPONSE: 0.3
;
_vrf_PLAT054_h027                
;
PROBLEM: Medium  Crystal Dimension Missing (or Error) ...     Please Check
RESPONSE: 0.1
;
_vrf_PLAT055_h027                
;
PROBLEM: Maximum Crystal Dimension Missing (or Error) ...     Please Check
RESPONSE: 0.1
;
# Added during the CSD deposition process: Tuesday 05 July 2016 10:54 AM
# end Validation Reply Form


_audit_creation_date             2016-06-10T11:04:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H13 B1 F2 N2 O2'
_chemical_formula_sum            'C16 H13 B F2 N2 O2'
_chemical_formula_weight         314.09
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   10.1732(10)
_cell_length_b                   7.3747(7)
_cell_length_c                   19.0117(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.747(2)
_cell_angle_gamma                90
_cell_volume                     1421.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_number            10887
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_full        26.34
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2887
_reflns_number_gt                2458
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0561P)²+0.2165P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2887
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.28200(12) 0.62296(16) 0.24262(6) 0.0371(3) Uani 1 1 d . . .
C2 C 0.27800(14) 0.59494(19) 0.31472(7) 0.0478(3) Uani 1 1 d . . .
H2 H 0.1999 0.5575 0.3324 0.057 Uiso 1 1 calc R . .
C3 C 0.38882(16) 0.6221(2) 0.36009(8) 0.0569(4) Uani 1 1 d . . .
H3 H 0.3854 0.6051 0.4084 0.068 Uiso 1 1 calc R . .
C4 C 0.50527(15) 0.6749(2) 0.33348(9) 0.0576(4) Uani 1 1 d . . .
H4 H 0.5807 0.6908 0.364 0.069 Uiso 1 1 calc R . .
C5 C 0.51058(13) 0.70403(19) 0.26255(8) 0.0509(4) Uani 1 1 d . . .
H5 H 0.5895 0.7401 0.2454 0.061 Uiso 1 1 calc R . .
C6 C 0.39907(12) 0.68017(16) 0.21592(7) 0.0398(3) Uani 1 1 d . . .
C7 C 0.31856(12) 0.82046(17) 0.10503(7) 0.0413(3) Uani 1 1 d . . .
C8 C 0.19917(12) 0.87670(16) 0.14310(7) 0.0396(3) Uani 1 1 d . . .
H8A H 0.2268 0.9282 0.1889 0.047 Uiso 1 1 calc R . .
H8B H 0.1472 0.9662 0.1157 0.047 Uiso 1 1 calc R . .
C9 C 0.12069(11) 0.70789(16) 0.15125(6) 0.0350(3) Uani 1 1 d . . .
C10 C 0.00362(11) 0.66744(17) 0.10552(6) 0.0385(3) Uani 1 1 d . . .
C11 C -0.06395(13) 0.8003(2) 0.06360(7) 0.0491(3) Uani 1 1 d . . .
H11 H -0.036 0.9203 0.0666 0.059 Uiso 1 1 calc R . .
C12 C -0.17053(15) 0.7547(2) 0.01838(8) 0.0596(4) Uani 1 1 d . . .
H12 H -0.2163 0.8437 -0.0082 0.072 Uiso 1 1 calc R . .
C13 C -0.20995(14) 0.5742(3) 0.01247(8) 0.0600(4) Uani 1 1 d . . .
H13 H -0.2805 0.5431 -0.0195 0.072 Uiso 1 1 calc R . .
C14 C -0.14703(14) 0.4420(2) 0.05271(7) 0.0545(4) Uani 1 1 d . . .
H14 H -0.1744 0.322 0.0479 0.065 Uiso 1 1 calc R . .
C15 C -0.04162(12) 0.48777(19) 0.10096(7) 0.0433(3) Uani 1 1 d . . .
C16 C 0.52558(14) 0.6561(2) 0.10979(9) 0.0595(4) Uani 1 1 d . . .
H16A H 0.5027 0.6288 0.0609 0.089 Uiso 1 1 calc R . .
H16B H 0.5624 0.5503 0.1333 0.089 Uiso 1 1 calc R . .
H16C H 0.5893 0.7524 0.1134 0.089 Uiso 1 1 calc R . .
B1 B 0.08997(14) 0.39884(19) 0.20571(8) 0.0418(3) Uani 1 1 d . . .
F1 F 0.1807(5) 0.2676(7) 0.2256(2) 0.0600(9) Uani 0.78(3) 1 d P A 1
F2 F 0.0056(2) 0.4253(5) 0.25935(18) 0.0527(10) Uani 0.78(3) 1 d P A 1
F1B F 0.023(3) 0.396(4) 0.2549(9) 0.118(6) Uani 0.22(3) 1 d P A 2
F2B F 0.190(2) 0.276(3) 0.203(3) 0.109(8) Uani 0.22(3) 1 d P A 2
N1 N 0.16528(9) 0.58763(13) 0.19743(5) 0.0347(2) Uani 1 1 d . A .
N2 N 0.40674(10) 0.71271(15) 0.14304(6) 0.0429(3) Uani 1 1 d . . .
O1 O 0.33121(10) 0.86341(15) 0.04418(5) 0.0571(3) Uani 1 1 d . . .
O2 O 0.01802(10) 0.35589(13) 0.13999(5) 0.0509(3) Uani 1 1 d . A .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.3901(18) . ?
C1 C6 1.3979(17) . ?
C1 N1 1.4308(15) . ?
C2 C3 1.376(2) . ?
C2 H2 0.93 . ?
C3 C4 1.382(2) . ?
C3 H3 0.93 . ?
C4 C5 1.371(2) . ?
C4 H4 0.93 . ?
C5 C6 1.3919(19) . ?
C5 H5 0.93 . ?
C6 N2 1.4147(18) . ?
C7 O1 1.2165(16) . ?
C7 N2 1.3605(17) . ?
C7 C8 1.5221(17) . ?
C8 C9 1.4940(16) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N1 1.3029(16) . ?
C9 C10 1.4463(17) . ?
C10 C15 1.4030(19) . ?
C10 C11 1.4060(19) . ?
C11 C12 1.369(2) . ?
C11 H11 0.93 . ?
C12 C13 1.392(2) . ?
C12 H12 0.93 . ?
C13 C14 1.366(2) . ?
C13 H13 0.93 . ?
C14 C15 1.3938(19) . ?
C14 H14 0.93 . ?
C15 O2 1.3380(17) . ?
C16 N2 1.4703(16) . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
B1 F1B 1.20(3) . ?
B1 F1 1.369(5) . ?
B1 F2B 1.37(2) . ?
B1 F2 1.400(4) . ?
B1 O2 1.4302(19) . ?
B1 N1 1.6031(16) . ?

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 C6 119.89(12) . . ?
C2 C1 N1 118.32(11) . . ?
C6 C1 N1 121.78(11) . . ?
C3 C2 C1 120.46(13) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.61(14) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.59(13) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.69(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.74(13) . . ?
C5 C6 N2 119.62(11) . . ?
C1 C6 N2 121.63(11) . . ?
O1 C7 N2 122.70(12) . . ?
O1 C7 C8 122.18(12) . . ?
N2 C7 C8 115.06(11) . . ?
C9 C8 C7 106.05(10) . . ?
C9 C8 H8A 110.5 . . ?
C7 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
N1 C9 C10 119.22(11) . . ?
N1 C9 C8 118.55(11) . . ?
C10 C9 C8 122.01(11) . . ?
C15 C10 C11 118.73(12) . . ?
C15 C10 C9 118.78(11) . . ?
C11 C10 C9 122.45(12) . . ?
C12 C11 C10 120.63(15) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.57(15) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 121.27(14) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.69(15) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
O2 C15 C14 118.55(13) . . ?
O2 C15 C10 121.39(11) . . ?
C14 C15 C10 120.00(13) . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F1B B1 F1 100.5(16) . . ?
F1B B1 F2B 119.5(13) . . ?
F1 B1 F2B 19(2) . . ?
F1B B1 F2 9.9(17) . . ?
F1 B1 F2 109.7(2) . . ?
F2B B1 F2 129(2) . . ?
F1B B1 O2 113.2(9) . . ?
F1 B1 O2 111.7(2) . . ?
F2B B1 O2 98.3(18) . . ?
F2 B1 O2 111.52(16) . . ?
F1B B1 N1 113.5(12) . . ?
F1 B1 N1 108.9(2) . . ?
F2B B1 N1 101.9(12) . . ?
F2 B1 N1 106.11(18) . . ?
O2 B1 N1 108.71(11) . . ?
C9 N1 C1 120.40(10) . . ?
C9 N1 B1 120.98(10) . . ?
C1 N1 B1 118.61(10) . . ?
C7 N2 C6 122.14(10) . . ?
C7 N2 C16 117.83(12) . . ?
C6 N2 C16 119.14(12) . . ?
C15 O2 B1 119.95(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
C6 C1 C2 C3 -0.4(2) . . . . ?
N1 C1 C2 C3 178.16(12) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 -1.1(2) . . . . ?
C4 C5 C6 N2 179.41(12) . . . . ?
C2 C1 C6 C5 1.40(18) . . . . ?
N1 C1 C6 C5 -177.08(11) . . . . ?
C2 C1 C6 N2 -179.08(11) . . . . ?
N1 C1 C6 N2 2.44(18) . . . . ?
O1 C7 C8 C9 109.22(13) . . . . ?
N2 C7 C8 C9 -68.13(14) . . . . ?
C7 C8 C9 N1 73.19(13) . . . . ?
C7 C8 C9 C10 -101.40(12) . . . . ?
N1 C9 C10 C15 -14.00(16) . . . . ?
C8 C9 C10 C15 160.56(11) . . . . ?
N1 C9 C10 C11 168.25(11) . . . . ?
C8 C9 C10 C11 -17.20(17) . . . . ?
C15 C10 C11 C12 -1.05(19) . . . . ?
C9 C10 C11 C12 176.71(12) . . . . ?
C10 C11 C12 C13 -1.8(2) . . . . ?
C11 C12 C13 C14 2.2(2) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 O2 179.70(12) . . . . ?
C13 C14 C15 C10 -3.20(19) . . . . ?
C11 C10 C15 O2 -179.43(11) . . . . ?
C9 C10 C15 O2 2.73(17) . . . . ?
C11 C10 C15 C14 3.55(18) . . . . ?
C9 C10 C15 C14 -174.29(11) . . . . ?
C10 C9 N1 C1 179.06(10) . . . . ?
C8 C9 N1 C1 4.32(15) . . . . ?
C10 C9 N1 B1 -1.82(16) . . . . ?
C8 C9 N1 B1 -176.56(10) . . . . ?
C2 C1 N1 C9 130.07(12) . . . . ?
C6 C1 N1 C9 -51.43(16) . . . . ?
C2 C1 N1 B1 -49.07(15) . . . . ?
C6 C1 N1 B1 129.43(12) . . . . ?
F1B B1 N1 C9 -100.6(15) . . . . ?
F1 B1 N1 C9 148.3(2) . . . . ?
F2B B1 N1 C9 130(2) . . . . ?
F2 B1 N1 C9 -93.69(17) . . . . ?
O2 B1 N1 C9 26.37(15) . . . . ?
F1B B1 N1 C1 78.5(15) . . . . ?
F1 B1 N1 C1 -32.6(2) . . . . ?
F2B B1 N1 C1 -51(2) . . . . ?
F2 B1 N1 C1 85.44(16) . . . . ?
O2 B1 N1 C1 -154.50(10) . . . . ?
O1 C7 N2 C6 172.79(12) . . . . ?
C8 C7 N2 C6 -9.88(16) . . . . ?
O1 C7 N2 C16 3.74(19) . . . . ?
C8 C7 N2 C16 -178.93(11) . . . . ?
C5 C6 N2 C7 -129.51(13) . . . . ?
C1 C6 N2 C7 50.98(17) . . . . ?
C5 C6 N2 C16 39.39(17) . . . . ?
C1 C6 N2 C16 -140.11(13) . . . . ?
C14 C15 O2 B1 -156.93(12) . . . . ?
C10 C15 O2 B1 26.01(17) . . . . ?
F1B B1 O2 C15 89.2(18) . . . . ?
F1 B1 O2 C15 -158.1(2) . . . . ?
F2B B1 O2 C15 -143.6(18) . . . . ?
F2 B1 O2 C15 78.7(2) . . . . ?
N1 B1 O2 C15 -37.92(15) . . . . ?

# END of CIF

