# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1062920'
_audit_update_record             
;
2015-05-01 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 B F2 N4 O'
_chemical_formula_weight         298.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   10.213(2)
_cell_length_b                   9.1955(18)
_cell_length_c                   13.667(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.03(3)
_cell_angle_gamma                90
_cell_volume                     1239.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4288
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.234
_diffrn_reflns_theta_max         25.644
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2252
_reflns_number_gt                1546
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2014
_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     
'w=1/[σ²(Fo²)+(0.1506P)²+0.1851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.013(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2252
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2461
_refine_ls_wR_factor_gt          0.2081
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2484(3) 0.0238(4) 0.5374(2) 0.0651(8) Uani 1 1 d . . . . .
C2 C 0.1698(3) 0.1225(4) 0.5737(3) 0.0737(10) Uani 1 1 d . . . . .
H2A H 0.1864 0.1414 0.6427 0.088 Uiso 1 1 calc R U . . .
C3 C 0.0669(4) 0.1916(4) 0.5051(3) 0.0817(10) Uani 1 1 d . . . . .
H3A H 0.0120 0.2571 0.5278 0.098 Uiso 1 1 calc R U . . .
C4 C 0.0434(4) 0.1646(4) 0.4009(3) 0.0819(11) Uani 1 1 d . . . . .
H4A H -0.0262 0.2130 0.3550 0.098 Uiso 1 1 calc R U . . .
C5 C 0.1216(3) 0.0683(4) 0.3670(3) 0.0738(10) Uani 1 1 d . . . . .
H5A H 0.1061 0.0498 0.2981 0.089 Uiso 1 1 calc R U . . .
C6 C 0.3167(3) -0.1025(4) 0.4193(2) 0.0654(8) Uani 1 1 d . . . . .
H6A H 0.3226 -0.1388 0.3570 0.079 Uiso 1 1 calc R U . . .
C7 C 0.3977(3) -0.1383(4) 0.5124(2) 0.0638(8) Uani 1 1 d . . . . .
C8 C 0.5102(3) -0.2298(4) 0.5529(2) 0.0640(8) Uani 1 1 d . . . . .
C9 C 0.5646(3) -0.3603(4) 0.4071(2) 0.0711(9) Uani 1 1 d . . . . .
H9A H 0.4993 -0.3142 0.3565 0.085 Uiso 1 1 calc R U . . .
C10 C 0.6471(3) -0.4615(4) 0.3835(3) 0.0753(10) Uani 1 1 d . . . . .
H10A H 0.6370 -0.4866 0.3160 0.090 Uiso 1 1 calc R U . . .
C11 C 0.7478(3) -0.5293(4) 0.4592(3) 0.0790(10) Uani 1 1 d . . . . .
H11A H 0.8045 -0.5979 0.4415 0.095 Uiso 1 1 calc R U . . .
C12 C 0.7631(3) -0.4956(4) 0.5582(3) 0.0767(10) Uani 1 1 d . . . . .
H12A H 0.8299 -0.5411 0.6082 0.092 Uiso 1 1 calc R U . . .
C13 C 0.6784(3) -0.3925(4) 0.5844(2) 0.0668(9) Uani 1 1 d . . . . .
C14 C 0.5707(3) -0.2423(4) 0.6546(2) 0.0690(9) Uani 1 1 d . . . . .
B1 B 0.4080(4) -0.0845(5) 0.7023(3) 0.0745(11) Uani 1 1 d . . . . .
F1 F 0.4251(3) 0.0426(3) 0.75224(18) 0.1326(12) Uani 1 1 d . . . . .
F2 F 0.3103(2) -0.1675(4) 0.73069(19) 0.1226(12) Uani 1 1 d . . . . .
N1 N 0.2241(2) -0.0015(3) 0.43572(18) 0.0643(7) Uani 1 1 d . . . . .
N2 N 0.3555(2) -0.0595(3) 0.58597(18) 0.0648(7) Uani 1 1 d . . . . .
N3 N 0.5785(2) -0.3267(3) 0.50680(19) 0.0629(7) Uani 1 1 d . . . . .
N4 N 0.6732(3) -0.3403(3) 0.6756(2) 0.0726(8) Uani 1 1 d . . . . .
O1 O 0.5344(2) -0.1665(3) 0.72692(16) 0.0809(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.359(4) . ?
C1 N1 1.366(4) . ?
C1 C2 1.387(5) . ?
C2 C3 1.369(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.404(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.351(5) . ?
C4 H4A 0.9300 . ?
C5 N1 1.372(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.366(4) . ?
C6 N1 1.384(4) . ?
C6 H6A 0.9300 . ?
C7 N2 1.396(4) . ?
C7 C8 1.415(5) . ?
C8 C14 1.372(4) . ?
C8 N3 1.381(4) . ?
C9 C10 1.350(5) . ?
C9 N3 1.368(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.402(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.356(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.392(5) . ?
C12 H12A 0.9300 . ?
C13 N4 1.350(4) . ?
C13 N3 1.403(4) . ?
C14 O1 1.338(4) . ?
C14 N4 1.354(4) . ?
B1 F1 1.342(5) . ?
B1 F2 1.390(5) . ?
B1 O1 1.457(5) . ?
B1 N2 1.557(5) . ?

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
N2 C1 N1 108.1(3) . . ?
N2 C1 C2 131.4(3) . . ?
N1 C1 C2 120.4(3) . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 N1 119.1(3) . . ?
C4 C5 H5A 120.4 . . ?
N1 C5 H5A 120.4 . . ?
C7 C6 N1 106.5(3) . . ?
C7 C6 H6A 126.7 . . ?
N1 C6 H6A 126.7 . . ?
C6 C7 N2 108.7(3) . . ?
C6 C7 C8 137.9(3) . . ?
N2 C7 C8 113.4(3) . . ?
C14 C8 N3 105.0(3) . . ?
C14 C8 C7 123.6(3) . . ?
N3 C8 C7 131.3(3) . . ?
C10 C9 N3 119.0(3) . . ?
C10 C9 H9A 120.5 . . ?
N3 C9 H9A 120.5 . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
N4 C13 C12 131.0(3) . . ?
N4 C13 N3 110.5(3) . . ?
C12 C13 N3 118.5(3) . . ?
O1 C14 N4 122.5(3) . . ?
O1 C14 C8 124.5(3) . . ?
N4 C14 C8 113.1(3) . . ?
F1 B1 F2 110.2(3) . . ?
F1 B1 O1 110.0(3) . . ?
F2 B1 O1 108.0(3) . . ?
F1 B1 N2 110.8(4) . . ?
F2 B1 N2 106.5(3) . . ?
O1 B1 N2 111.2(3) . . ?
C1 N1 C5 121.4(3) . . ?
C1 N1 C6 109.2(3) . . ?
C5 N1 C6 129.4(3) . . ?
C1 N2 C7 107.5(3) . . ?
C1 N2 B1 127.0(3) . . ?
C7 N2 B1 124.8(3) . . ?
C9 N3 C8 131.7(3) . . ?
C9 N3 C13 121.5(3) . . ?
C8 N3 C13 106.7(3) . . ?
C13 N4 C14 104.7(3) . . ?
C14 O1 B1 119.9(3) . . ?

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
N2 C1 C2 C3 179.8(3) . . . . ?
N1 C1 C2 C3 0.9(5) . . . . ?
C1 C2 C3 C4 -1.0(6) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 N1 -0.3(5) . . . . ?
N1 C6 C7 N2 -0.1(4) . . . . ?
N1 C6 C7 C8 -179.3(4) . . . . ?
C6 C7 C8 C14 -179.7(4) . . . . ?
N2 C7 C8 C14 1.2(5) . . . . ?
C6 C7 C8 N3 -3.1(7) . . . . ?
N2 C7 C8 N3 177.7(3) . . . . ?
N3 C9 C10 C11 -1.4(5) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C10 C11 C12 C13 -0.2(6) . . . . ?
C11 C12 C13 N4 -179.7(4) . . . . ?
C11 C12 C13 N3 0.3(5) . . . . ?
N3 C8 C14 O1 -179.9(3) . . . . ?
C7 C8 C14 O1 -2.5(6) . . . . ?
N3 C8 C14 N4 0.3(4) . . . . ?
C7 C8 C14 N4 177.7(3) . . . . ?
N2 C1 N1 C5 -179.7(3) . . . . ?
C2 C1 N1 C5 -0.5(5) . . . . ?
N2 C1 N1 C6 0.2(4) . . . . ?
C2 C1 N1 C6 179.3(3) . . . . ?
C4 C5 N1 C1 0.2(5) . . . . ?
C4 C5 N1 C6 -179.6(3) . . . . ?
C7 C6 N1 C1 0.0(4) . . . . ?
C7 C6 N1 C5 179.8(3) . . . . ?
N1 C1 N2 C7 -0.3(3) . . . . ?
C2 C1 N2 C7 -179.3(3) . . . . ?
N1 C1 N2 B1 -170.8(3) . . . . ?
C2 C1 N2 B1 10.3(6) . . . . ?
C6 C7 N2 C1 0.3(4) . . . . ?
C8 C7 N2 C1 179.7(3) . . . . ?
C6 C7 N2 B1 171.0(3) . . . . ?
C8 C7 N2 B1 -9.6(5) . . . . ?
F1 B1 N2 C1 -50.6(5) . . . . ?
F2 B1 N2 C1 69.3(5) . . . . ?
O1 B1 N2 C1 -173.3(3) . . . . ?
F1 B1 N2 C7 140.5(3) . . . . ?
F2 B1 N2 C7 -99.7(4) . . . . ?
O1 B1 N2 C7 17.7(5) . . . . ?
C10 C9 N3 C8 179.9(3) . . . . ?
C10 C9 N3 C13 1.5(5) . . . . ?
C14 C8 N3 C9 -179.0(3) . . . . ?
C7 C8 N3 C9 4.0(6) . . . . ?
C14 C8 N3 C13 -0.4(3) . . . . ?
C7 C8 N3 C13 -177.4(3) . . . . ?
N4 C13 N3 C9 179.1(3) . . . . ?
C12 C13 N3 C9 -0.9(5) . . . . ?
N4 C13 N3 C8 0.3(4) . . . . ?
C12 C13 N3 C8 -179.7(3) . . . . ?
C12 C13 N4 C14 179.9(4) . . . . ?
N3 C13 N4 C14 -0.1(4) . . . . ?
O1 C14 N4 C13 -179.9(3) . . . . ?
C8 C14 N4 C13 -0.1(4) . . . . ?
N4 C14 O1 B1 -168.1(3) . . . . ?
C8 C14 O1 B1 12.2(5) . . . . ?
F1 B1 O1 C14 -141.1(3) . . . . ?
F2 B1 O1 C14 98.6(4) . . . . ?
N2 B1 O1 C14 -17.9(5) . . . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.067



#===END 

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1062921'
_audit_update_record             
;
2015-05-01 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 B Cl F2 N4 O5'
_chemical_formula_weight         398.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.522(4)
_cell_length_b                   5.1557(9)
_cell_length_c                   15.049(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.992(2)
_cell_angle_gamma                90
_cell_volume                     1576.8(5)
_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       columnar
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_absorpt_coefficient_mu    0.303
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11547
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.002
_diffrn_reflns_theta_max         27.275
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3270
_reflns_number_gt                2774
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2014
_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     
'w=1/[σ²(Fo²)+(0.0686P)²+0.7448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0116(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3270
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.12987(10) 0.0198(5) 0.69699(15) 0.0397(5) Uani 1 1 d . . . . .
C2 C 0.06154(11) 0.0031(5) 0.67331(18) 0.0507(6) Uani 1 1 d . . . . .
H2A H 0.0333 0.0991 0.7038 0.061 Uiso 1 1 calc R U . . .
C3 C 0.03744(12) -0.1564(7) 0.6049(2) 0.0623(8) Uani 1 1 d . . . . .
H3A H -0.0078 -0.1707 0.5886 0.075 Uiso 1 1 calc R U . . .
C4 C 0.08026(13) -0.3010(7) 0.5581(2) 0.0670(8) Uani 1 1 d . . . . .
H4A H 0.0629 -0.4068 0.5105 0.080 Uiso 1 1 calc R U . . .
C5 C 0.14594(12) -0.2869(6) 0.58166(18) 0.0572(7) Uani 1 1 d . . . . .
H5A H 0.1742 -0.3839 0.5515 0.069 Uiso 1 1 calc R U . . .
C6 C 0.23528(10) -0.0763(4) 0.68670(15) 0.0391(5) Uani 1 1 d . . . . .
H6A H 0.2727 -0.1500 0.6687 0.047 Uiso 1 1 calc R U . . .
C7 C 0.23315(9) 0.1006(4) 0.75242(14) 0.0329(4) Uani 1 1 d . . . . .
C8 C 0.27976(9) 0.2511(4) 0.81059(13) 0.0324(4) Uani 1 1 d . . . . .
C9 C 0.39318(10) 0.0905(4) 0.79434(13) 0.0311(4) Uani 1 1 d . . . . .
H9A H 0.3791 -0.0494 0.7576 0.037 Uiso 1 1 calc R U . . .
C10 C 0.45824(10) 0.1369(4) 0.81859(13) 0.0346(4) Uani 1 1 d . . . . .
H10A H 0.4890 0.0249 0.7995 0.042 Uiso 1 1 calc R U . . .
C11 C 0.47997(10) 0.3517(4) 0.87221(13) 0.0356(5) Uani 1 1 d . . . . .
H11A H 0.5248 0.3837 0.8867 0.043 Uiso 1 1 calc R U . . .
C12 C 0.43521(10) 0.5145(4) 0.90332(13) 0.0340(4) Uani 1 1 d . . . . .
H12A H 0.4489 0.6565 0.9393 0.041 Uiso 1 1 calc R U . . .
C13 C 0.36884(10) 0.4601(4) 0.87930(13) 0.0306(4) Uani 1 1 d . . . . .
C14 C 0.25992(10) 0.4544(4) 0.85894(14) 0.0350(5) Uani 1 1 d . . . . .
B1 B 0.14474(12) 0.3466(6) 0.83277(18) 0.0414(6) Uani 1 1 d . . . . .
Cl1 Cl 0.35636(2) 0.42537(10) 0.57796(3) 0.03577(19) Uani 1 1 d . . . . .
F1 F 0.09198(7) 0.4889(3) 0.79557(11) 0.0599(4) Uani 1 1 d . . . . .
F2 F 0.12988(8) 0.2007(3) 0.90326(10) 0.0628(4) Uani 1 1 d . . . . .
N1 N 0.17036(9) -0.1259(4) 0.65138(13) 0.0417(4) Uani 1 1 d . . . . .
N2 N 0.16787(8) 0.1617(4) 0.75945(12) 0.0370(4) Uani 1 1 d . . . . .
N3 N 0.34849(8) 0.2536(3) 0.82496(10) 0.0282(4) Uani 1 1 d . . . . .
N4 N 0.31406(9) 0.5827(4) 0.89931(13) 0.0364(4) Uani 1 1 d . . . . .
H4 H 0.3119(12) 0.682(5) 0.9341(18) 0.040(7) Uiso 1 1 d . . . . .
O1 O 0.19974(7) 0.5290(3) 0.86483(11) 0.0453(4) Uani 1 1 d . . . . .
O2 O 0.29494(10) 0.5126(5) 0.53075(15) 0.0776(7) Uani 1 1 d . . . . .
O3 O 0.36976(10) 0.5585(3) 0.66185(11) 0.0516(4) Uani 1 1 d . . . . .
O4 O 0.40584(11) 0.4923(4) 0.52367(13) 0.0720(6) Uani 1 1 d . . . . .
O5 O 0.35674(10) 0.1518(3) 0.59107(12) 0.0559(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.350(3) . ?
C1 N1 1.373(3) . ?
C1 C2 1.401(3) . ?
C2 C3 1.356(4) . ?
C3 C4 1.413(4) . ?
C4 C5 1.347(4) . ?
C5 N1 1.377(3) . ?
C6 C7 1.351(3) . ?
C6 N1 1.388(3) . ?
C7 N2 1.394(2) . ?
C7 C8 1.432(3) . ?
C8 C14 1.370(3) . ?
C8 N3 1.397(2) . ?
C9 C10 1.356(3) . ?
C9 N3 1.370(2) . ?
C10 C11 1.406(3) . ?
C11 C12 1.374(3) . ?
C12 C13 1.388(3) . ?
C13 N4 1.359(3) . ?
C13 N3 1.372(3) . ?
C14 O1 1.308(2) . ?
C14 N4 1.361(3) . ?
B1 F1 1.362(3) . ?
B1 F2 1.369(3) . ?
B1 O1 1.497(3) . ?
B1 N2 1.580(3) . ?
Cl1 O5 1.4238(18) . ?
Cl1 O3 1.4296(17) . ?
Cl1 O2 1.431(2) . ?
Cl1 O4 1.4313(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 108.25(18) . . ?
N2 C1 C2 132.2(2) . . ?
N1 C1 C2 119.6(2) . . ?
C3 C2 C1 118.5(2) . . ?
C2 C3 C4 120.8(2) . . ?
C5 C4 C3 120.6(3) . . ?
C4 C5 N1 118.6(2) . . ?
C7 C6 N1 106.13(18) . . ?
C6 C7 N2 109.71(18) . . ?
C6 C7 C8 136.61(18) . . ?
N2 C7 C8 113.49(18) . . ?
C14 C8 N3 106.20(17) . . ?
C14 C8 C7 121.11(18) . . ?
N3 C8 C7 132.37(18) . . ?
C10 C9 N3 118.77(18) . . ?
C9 C10 C11 121.03(19) . . ?
C12 C11 C10 120.21(19) . . ?
C11 C12 C13 117.78(19) . . ?
N4 C13 N3 107.47(17) . . ?
N4 C13 C12 131.30(19) . . ?
N3 C13 C12 121.23(18) . . ?
O1 C14 N4 123.12(19) . . ?
O1 C14 C8 127.9(2) . . ?
N4 C14 C8 108.93(18) . . ?
F1 B1 F2 111.37(19) . . ?
F1 B1 O1 108.3(2) . . ?
F2 B1 O1 109.6(2) . . ?
F1 B1 N2 109.7(2) . . ?
F2 B1 N2 109.3(2) . . ?
O1 B1 N2 108.54(16) . . ?
O5 Cl1 O3 110.88(11) . . ?
O5 Cl1 O2 111.58(13) . . ?
O3 Cl1 O2 109.61(13) . . ?
O5 Cl1 O4 109.10(12) . . ?
O3 Cl1 O4 108.88(12) . . ?
O2 Cl1 O4 106.66(15) . . ?
C1 N1 C5 121.97(19) . . ?
C1 N1 C6 108.87(18) . . ?
C5 N1 C6 129.2(2) . . ?
C1 N2 C7 107.04(17) . . ?
C1 N2 B1 127.76(17) . . ?
C7 N2 B1 125.04(18) . . ?
C9 N3 C13 120.95(17) . . ?
C9 N3 C8 130.60(17) . . ?
C13 N3 C8 108.45(16) . . ?
C13 N4 C14 108.91(18) . . ?
C14 O1 B1 118.04(18) . . ?

_refine_diff_density_max         0.716
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.075



#===END 

