# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_151214a_0m
_database_code_depnum_ccdc_archive 'CCDC 1541739'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2g
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 B F2 N2 O2'
_chemical_formula_weight         328.12

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6560(9)
_cell_length_b                   10.0738(11)
_cell_length_c                   11.2184(12)
_cell_angle_alpha                112.3050(10)
_cell_angle_beta                 97.3120(10)
_cell_angle_gamma                91.8680(10)
_cell_volume                     790.88(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5327
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9761
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9036
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.55
_reflns_number_total             3535
_reflns_number_gt                2811
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0582P)²+0.0980P] 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
_refine_ls_extinction_coef       0.036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3535
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
N1 N 0.18404(14) 0.80295(10) 0.61064(10) 0.0529(3) Uani 1 1 d . . .
N2 N 0.21485(14) 0.66423(10) 0.60359(10) 0.0520(3) Uani 1 1 d . . .
O1 O 0.17594(14) 0.80849(9) 0.81289(9) 0.0622(3) Uani 1 1 d . . .
O2 O 0.38520(16) -0.25783(10) 0.23970(12) 0.0800(3) Uani 1 1 d . . .
B1 B 0.2091(2) 0.65792(15) 0.74273(15) 0.0575(4) Uani 1 1 d . . .
F1 F 0.07271(12) 0.56380(8) 0.73842(9) 0.0738(3) Uani 1 1 d . . .
F2 F 0.36665(12) 0.62427(10) 0.79084(9) 0.0787(3) Uani 1 1 d . . .
C2 C 0.13096(16) 1.02714(12) 0.77863(12) 0.0489(3) Uani 1 1 d . . .
C1 C 0.16429(16) 0.87469(12) 0.73047(12) 0.0494(3) Uani 1 1 d . . .
C11 C 0.32930(16) 0.17695(13) 0.33057(13) 0.0537(3) Uani 1 1 d . . .
C9 C 0.27435(18) 0.42459(13) 0.47771(14) 0.0576(3) Uani 1 1 d . . .
H9 H 0.2726 0.3964 0.5475 0.069 Uiso 1 1 calc R . .
C7 C 0.1152(2) 1.09831(14) 0.69390(14) 0.0627(4) Uani 1 1 d . . .
H7 H 0.1251 1.0488 0.6066 0.075 Uiso 1 1 calc R . .
C8 C 0.24529(17) 0.56865(13) 0.49505(13) 0.0551(3) Uani 1 1 d . . .
H8 H 0.2483 0.5955 0.4246 0.066 Uiso 1 1 calc R . .
C14 C 0.36896(17) -0.11654(14) 0.26120(14) 0.0603(3) Uani 1 1 d . . .
C10 C 0.30434(17) 0.32810(14) 0.36275(14) 0.0565(3) Uani 1 1 d . . .
H10 H 0.3097 0.3617 0.2966 0.068 Uiso 1 1 calc R . .
C3 C 0.1130(2) 1.10112(15) 0.90733(13) 0.0611(3) Uani 1 1 d . . .
H3 H 0.1211 1.0540 0.9646 0.073 Uiso 1 1 calc R . .
C13 C 0.38616(19) -0.05461(15) 0.17287(14) 0.0679(4) Uani 1 1 d . . .
H13 H 0.4110 -0.1099 0.0903 0.081 Uiso 1 1 calc R . .
C16 C 0.3150(2) 0.11110(14) 0.41801(14) 0.0658(4) Uani 1 1 d . . .
H16 H 0.2929 0.1661 0.5015 0.079 Uiso 1 1 calc R . .
C6 C 0.0849(2) 1.24194(14) 0.73852(15) 0.0701(4) Uani 1 1 d . . .
H6 H 0.0741 1.2890 0.6812 0.084 Uiso 1 1 calc R . .
C12 C 0.36621(19) 0.09146(15) 0.20797(14) 0.0635(3) Uani 1 1 d . . .
H12 H 0.3779 0.1330 0.1478 0.076 Uiso 1 1 calc R . .
C15 C 0.3328(2) -0.03297(15) 0.38400(15) 0.0692(4) Uani 1 1 d . . .
H15 H 0.3204 -0.0749 0.4438 0.083 Uiso 1 1 calc R . .
C4 C 0.0827(2) 1.24581(15) 0.95163(15) 0.0708(4) Uani 1 1 d . . .
H4 H 0.0706 1.2955 1.0385 0.085 Uiso 1 1 calc R . .
C5 C 0.0706(2) 1.31561(14) 0.86740(16) 0.0681(4) Uani 1 1 d . . .
H5 H 0.0527 1.4130 0.8977 0.082 Uiso 1 1 calc R . .
C17 C 0.4209(3) -0.35058(18) 0.1154(2) 0.0956(6) Uani 1 1 d . . .
H17A H 0.3277 -0.3509 0.0494 0.143 Uiso 1 1 calc R . .
H17B H 0.4279 -0.4465 0.1131 0.143 Uiso 1 1 calc R . .
H17C H 0.5312 -0.3171 0.0999 0.143 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
N1 C1 1.2938(15) . ?
N1 N2 1.3990(13) . ?
N2 C8 1.2887(16) . ?
N2 B1 1.5922(18) . ?
O1 C1 1.3261(14) . ?
O1 B1 1.4678(17) . ?
O2 C14 1.3631(16) . ?
O2 C17 1.420(2) . ?
B1 F2 1.3640(18) . ?
B1 F1 1.3711(18) . ?
C2 C3 1.3783(18) . ?
C2 C7 1.3878(18) . ?
C2 C1 1.4651(16) . ?
C11 C12 1.3889(18) . ?
C11 C16 1.389(2) . ?
C11 C10 1.4507(17) . ?
C9 C10 1.3413(18) . ?
C9 C8 1.4182(17) . ?
C9 H9 0.9300 . ?
C7 C6 1.3782(18) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C14 C13 1.373(2) . ?
C14 C15 1.384(2) . ?
C10 H10 0.9300 . ?
C3 C4 1.3881(19) . ?
C3 H3 0.9300 . ?
C13 C12 1.3906(19) . ?
C13 H13 0.9300 . ?
C16 C15 1.3697(19) . ?
C16 H16 0.9300 . ?
C6 C5 1.373(2) . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C4 C5 1.372(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C1 N1 N2 105.10(9) . . ?
C8 N2 N1 119.18(10) . . ?
C8 N2 B1 131.61(10) . . ?
N1 N2 B1 109.19(9) . . ?
C1 O1 B1 108.84(10) . . ?
C14 O2 C17 118.00(14) . . ?
F2 B1 F1 111.04(11) . . ?
F2 B1 O1 112.65(12) . . ?
F1 B1 O1 111.97(12) . . ?
F2 B1 N2 111.34(11) . . ?
F1 B1 N2 111.35(12) . . ?
O1 B1 N2 97.88(9) . . ?
C3 C2 C7 119.23(12) . . ?
C3 C2 C1 120.82(11) . . ?
C7 C2 C1 119.95(11) . . ?
N1 C1 O1 118.98(10) . . ?
N1 C1 C2 122.22(10) . . ?
O1 C1 C2 118.79(11) . . ?
C12 C11 C16 117.32(12) . . ?
C12 C11 C10 120.24(13) . . ?
C16 C11 C10 122.43(12) . . ?
C10 C9 C8 121.39(13) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C6 C7 C2 120.34(13) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N2 C8 C9 123.27(12) . . ?
N2 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
O2 C14 C13 125.51(13) . . ?
O2 C14 C15 114.77(14) . . ?
C13 C14 C15 119.72(12) . . ?
C9 C10 C11 126.97(13) . . ?
C9 C10 H10 116.5 . . ?
C11 C10 H10 116.5 . . ?
C2 C3 C4 120.11(13) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C14 C13 C12 119.44(13) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C16 C11 121.47(13) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C5 C6 C7 120.09(13) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C11 C12 C13 121.67(14) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C16 C15 C14 120.37(14) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C5 C4 C3 120.08(13) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.13(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.029
####################################################################### 
# 
# 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_151207b_0m
_database_code_depnum_ccdc_archive 'CCDC 1543020'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;
_audit_creation_date             2017-04-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        2h
_chemical_formula_moiety         'C20 H22 B F2 N3 O'
_chemical_formula_sum            'C20 H22 B F2 N3 O'
_chemical_formula_weight         369.21
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.4740(14)
_cell_length_b                   14.018(3)
_cell_length_c                   21.523(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.550(3)
_cell_angle_gamma                90
_cell_volume                     1952.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4889
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.72
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1188 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.7960.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12539
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         1.734
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_target            Mo
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2012
_reflns_number_total             3417
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.8468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1456
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
B1 B 1.1810(5) 0.8099(3) 1.00748(15) 0.0623(9) Uani 1 1 d . . . . .
C1 C 1.1150(4) 0.80405(19) 1.11090(12) 0.0549(7) Uani 1 1 d . . . . .
C2 C 1.1570(4) 0.78070(19) 1.17645(12) 0.0572(7) Uani 1 1 d . . . . .
C3 C 1.0069(5) 0.7955(2) 1.22002(13) 0.0756(9) Uani 1 1 d . . . . .
H3 H 0.8778 0.8191 1.2078 0.091 Uiso 1 1 calc R . . . .
C4 C 1.0506(6) 0.7748(2) 1.28231(15) 0.0908(11) Uani 1 1 d . . . . .
H4 H 0.9499 0.7845 1.3116 0.109 Uiso 1 1 calc R . . . .
C5 C 1.2398(7) 0.7403(2) 1.30078(16) 0.0875(11) Uani 1 1 d . . . . .
H5 H 1.2683 0.7277 1.3426 0.105 Uiso 1 1 calc R . . . .
C6 C 1.3878(6) 0.7243(2) 1.25741(16) 0.0868(10) Uani 1 1 d . . . . .
H6 H 1.5161 0.7000 1.2698 0.104 Uiso 1 1 calc R . . . .
C7 C 1.3468(5) 0.7441(2) 1.19553(14) 0.0729(9) Uani 1 1 d . . . . .
H7 H 1.4475 0.7327 1.1664 0.088 Uiso 1 1 calc R . . . .
C8 C 0.8236(4) 0.89630(19) 0.99345(11) 0.0561(7) Uani 1 1 d . . . . .
H8 H 0.7068 0.9172 1.0137 0.067 Uiso 1 1 calc R . . . .
C9 C 0.8330(4) 0.91149(19) 0.92875(11) 0.0562(7) Uani 1 1 d . . . . .
H9 H 0.9489 0.8913 0.9078 0.067 Uiso 1 1 calc R . . . .
C10 C 0.6771(4) 0.95473(19) 0.89669(12) 0.0566(7) Uani 1 1 d . . . . .
H10 H 0.5658 0.9741 0.9200 0.068 Uiso 1 1 calc R . . . .
C11 C 0.6604(4) 0.97475(18) 0.83115(11) 0.0524(7) Uani 1 1 d . . . . .
C12 C 0.4780(4) 1.01153(19) 0.80461(12) 0.0607(7) Uani 1 1 d . . . . .
H12 H 0.3706 1.0275 0.8305 0.073 Uiso 1 1 calc R . . . .
C13 C 0.4512(4) 1.0251(2) 0.74151(13) 0.0660(8) Uani 1 1 d . . . . .
H13 H 0.3262 1.0490 0.7260 0.079 Uiso 1 1 calc R . . . .
C14 C 0.6086(4) 1.0035(2) 0.70015(12) 0.0660(8) Uani 1 1 d . . . . .
C15 C 0.7953(4) 0.9697(2) 0.72723(12) 0.0700(8) Uani 1 1 d . . . . .
H15 H 0.9053 0.9564 0.7017 0.084 Uiso 1 1 calc R . . . .
C16 C 0.8194(4) 0.9561(2) 0.78997(12) 0.0630(8) Uani 1 1 d . . . . .
H16 H 0.9454 0.9337 0.8058 0.076 Uiso 1 1 calc R . . . .
C17 C 0.3796(5) 1.0353(3) 0.60725(15) 0.1041(13) Uani 1 1 d . . . . .
H17A H 0.2709 1.0126 0.6337 0.125 Uiso 1 1 calc R . . . .
H17B H 0.3684 1.0010 0.5681 0.125 Uiso 1 1 calc R . . . .
C18 C 0.3505(6) 1.1392(4) 0.59547(18) 0.1299(16) Uani 1 1 d . . . . .
H18A H 0.3586 1.1732 0.6342 0.195 Uiso 1 1 calc GR . . . .
H18B H 0.2176 1.1498 0.5758 0.195 Uiso 1 1 calc GR . . . .
H18C H 0.4566 1.1617 0.5688 0.195 Uiso 1 1 calc GR . . . .
C19 C 0.7559(6) 1.0020(3) 0.59473(16) 0.1079(13) Uani 1 1 d . . . . .
H19A H 0.8831 1.0242 0.6147 0.130 Uiso 1 1 calc R . . . .
H19B H 0.7311 1.0400 0.5576 0.130 Uiso 1 1 calc R . . . .
C20 C 0.7787(8) 0.8999(3) 0.57709(18) 0.146(2) Uani 1 1 d . . . . .
H20A H 0.8124 0.8629 0.6135 0.219 Uiso 1 1 calc GR . . . .
H20B H 0.8871 0.8937 0.5478 0.219 Uiso 1 1 calc GR . . . .
H20C H 0.6513 0.8772 0.5586 0.219 Uiso 1 1 calc GR . . . .
F1 F 1.1512(3) 0.73237(13) 0.96873(8) 0.0896(6) Uani 1 1 d . . . . .
F2 F 1.3060(2) 0.87600(14) 0.98014(8) 0.0892(6) Uani 1 1 d . . . . .
N1 N 0.9458(3) 0.84547(16) 1.09100(9) 0.0566(6) Uani 1 1 d . . . . .
N2 N 0.9688(3) 0.85473(15) 1.02647(9) 0.0528(6) Uani 1 1 d . . . . .
N3 N 0.5828(4) 1.0150(2) 0.63741(11) 0.0914(9) Uani 1 1 d . . . . .
O1 O 1.2577(3) 0.78177(15) 1.06949(8) 0.0711(6) 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
B1 F1 1.381(4) . ?
B1 F2 1.373(4) . ?
B1 N2 1.574(4) . ?
B1 O1 1.466(4) . ?
C1 C2 1.467(4) . ?
C1 N1 1.302(3) . ?
C1 O1 1.338(3) . ?
C2 C3 1.384(4) . ?
C2 C7 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.412(3) . ?
C8 N2 1.300(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.351(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.439(3) . ?
C11 C12 1.396(3) . ?
C11 C16 1.401(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.404(4) . ?
C14 C15 1.409(4) . ?
C14 N3 1.366(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.490(5) . ?
C17 N3 1.479(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.489(5) . ?
C19 N3 1.479(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 N2 1.407(3) . ?

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 N2 111.2(2) . . ?
F1 B1 O1 112.1(3) . . ?
F2 B1 F1 110.3(3) . . ?
F2 B1 N2 111.7(3) . . ?
F2 B1 O1 112.5(2) . . ?
O1 B1 N2 98.5(2) . . ?
N1 C1 C2 123.3(3) . . ?
N1 C1 O1 118.4(2) . . ?
O1 C1 C2 118.4(2) . . ?
C3 C2 C1 120.2(3) . . ?
C7 C2 C1 120.6(3) . . ?
C7 C2 C3 119.3(3) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C9 C8 H8 118.1 . . ?
N2 C8 H8 118.1 . . ?
N2 C8 C9 123.8(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 115.7 . . ?
C9 C10 C11 128.5(3) . . ?
C11 C10 H10 115.7 . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 C16 116.0(2) . . ?
C16 C11 C10 123.2(2) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 C11 122.5(3) . . ?
C13 C12 H12 118.8 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 116.0(2) . . ?
N3 C14 C13 122.0(3) . . ?
N3 C14 C15 121.9(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.0 . . ?
C11 C16 H16 118.9 . . ?
C15 C16 C11 122.2(3) . . ?
C15 C16 H16 118.9 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
N3 C17 H17A 109.3 . . ?
N3 C17 H17B 109.3 . . ?
N3 C17 C18 111.7(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
N3 C19 H19A 109.4 . . ?
N3 C19 H19B 109.4 . . ?
N3 C19 C20 111.0(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 N2 104.8(2) . . ?
C8 N2 B1 131.3(2) . . ?
C8 N2 N1 119.1(2) . . ?
N1 N2 B1 109.6(2) . . ?
C14 N3 C17 122.7(3) . . ?
C14 N3 C19 121.7(3) . . ?
C17 N3 C19 115.5(2) . . ?
C1 O1 B1 108.7(2) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_20180617c_0m
_database_code_depnum_ccdc_archive 'CCDC 1873749'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;
_audit_creation_date             2018-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_name_common            ?
_chemical_name_systematic        2d
_chemical_formula_moiety         'C16 H16 B F2 N3 O'
_chemical_formula_sum            'C16 H16 B F2 N3 O'
_chemical_formula_weight         315.13
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.5383(5)
_cell_length_b                   17.4670(11)
_cell_length_c                   10.2653(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.540(2)
_cell_angle_gamma                90
_cell_volume                     1601.53(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9517
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.87
_cell_measurement_theta_min      3.15
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0768 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.9254.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            33614
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         3.151
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2299
_reflns_number_total             3675
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²+0.4251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1525
_refine_special_details          ?
_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:
 C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F),
 C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00M(H00D,H00H,H00L), C00N(H00M,H00N,H00O)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
F001 F -0.04810(14) 0.59789(9) -0.08553(16) 0.1033(5) Uani 1 1 d . . . . .
F002 F 0.13764(19) 0.52994(8) -0.11494(15) 0.1045(5) Uani 1 1 d . . . . .
O003 O 0.14282(17) 0.66417(8) -0.13463(13) 0.0770(5) Uani 1 1 d . . . . .
N004 N 0.28142(17) 0.68224(8) 0.09115(15) 0.0541(4) Uani 1 1 d . . . . .
N005 N 0.20195(17) 0.61410(8) 0.08562(15) 0.0551(4) Uani 1 1 d . . . . .
C006 C 0.30181(19) 0.77486(10) -0.07548(17) 0.0509(4) Uani 1 1 d . . . . .
C007 C 0.24107(19) 0.70532(10) -0.03624(17) 0.0515(4) Uani 1 1 d . . . . .
C008 C 0.4032(2) 0.81904(10) 0.02664(18) 0.0557(5) Uani 1 1 d . . . . .
H008 H 0.4305 0.8048 0.1195 0.067 Uiso 1 1 calc R . . . .
C009 C 0.3043(2) 0.58815(11) 0.33905(19) 0.0576(5) Uani 1 1 d . . . . .
C00A C 0.2177(2) 0.57426(11) 0.1968(2) 0.0581(5) Uani 1 1 d . . . . .
H00A H 0.1632 0.5289 0.1807 0.070 Uiso 1 1 calc R . . . .
C00B C 0.4637(2) 0.88369(11) -0.0083(2) 0.0667(5) Uani 1 1 d . . . . .
H00B H 0.5325 0.9128 0.0606 0.080 Uiso 1 1 calc R . . . .
C00C C 0.3933(2) 0.65282(12) 0.3929(2) 0.0670(5) Uani 1 1 d . . . . .
H00C H 0.4030 0.6900 0.3318 0.080 Uiso 1 1 calc R . . . .
N00D N 0.5247(2) 0.62031(14) 0.76846(19) 0.0920(7) Uani 1 1 d . . . . .
C00E C 0.4225(2) 0.90543(12) -0.1457(2) 0.0719(6) Uani 1 1 d . . . . .
H00E H 0.4629 0.9495 -0.1694 0.086 Uiso 1 1 calc R . . . .
C00F C 0.2956(2) 0.53357(12) 0.4373(2) 0.0672(6) Uani 1 1 d . . . . .
H00F H 0.2397 0.4893 0.4059 0.081 Uiso 1 1 calc R . . . .
C00G C 0.3666(2) 0.54357(14) 0.5766(2) 0.0736(6) Uani 1 1 d . . . . .
H00G H 0.3571 0.5064 0.6378 0.088 Uiso 1 1 calc R . . . .
C00H C 0.4536(2) 0.60876(14) 0.6298(2) 0.0707(6) Uani 1 1 d . . . . .
C00I C 0.2624(3) 0.79694(14) -0.2127(2) 0.0777(6) Uani 1 1 d . . . . .
H00I H 0.1952 0.7677 -0.2826 0.093 Uiso 1 1 calc R . . . .
C00J C 0.4655(2) 0.66257(14) 0.5317(2) 0.0748(6) Uani 1 1 d . . . . .
H00J H 0.5244 0.7059 0.5630 0.090 Uiso 1 1 calc R . . . .
C00K C 0.3231(3) 0.86274(14) -0.2462(2) 0.0849(7) Uani 1 1 d . . . . .
H00K H 0.2954 0.8778 -0.3387 0.102 Uiso 1 1 calc R . . . .
B00L B 0.1000(3) 0.59758(14) -0.0689(2) 0.0687(6) Uani 1 1 d . . . . .
C00M C 0.6199(3) 0.68635(19) 0.8217(3) 0.1035(9) Uani 1 1 d . . . . .
H00D H 0.6994 0.6868 0.7846 0.155 Uiso 1 1 calc GR . . . .
H00H H 0.6617 0.6837 0.9214 0.155 Uiso 1 1 calc GR . . . .
H00L H 0.5618 0.7323 0.7944 0.155 Uiso 1 1 calc GR . . . .
C00N C 0.5076(4) 0.5663(2) 0.8699(3) 0.1180(11) Uani 1 1 d . . . . .
H00M H 0.4038 0.5531 0.8456 0.177 Uiso 1 1 calc GR . . . .
H00N H 0.5432 0.5892 0.9607 0.177 Uiso 1 1 calc GR . . . .
H00O H 0.5644 0.5209 0.8703 0.177 Uiso 1 1 calc GR . . . .


_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
F001 B00L 1.362(3) . ?
F002 B00L 1.367(3) . ?
O003 C007 1.323(2) . ?
O003 B00L 1.473(3) . ?
N004 N005 1.4015(19) . ?
N004 C007 1.291(2) . ?
N005 C00A 1.299(2) . ?
N005 B00L 1.569(3) . ?
C006 C007 1.462(2) . ?
C006 C008 1.385(2) . ?
C006 C00I 1.380(3) . ?
C008 H008 0.9300 . ?
C008 C00B 1.372(3) . ?
C009 C00A 1.424(3) . ?
C009 C00C 1.404(3) . ?
C009 C00F 1.411(3) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00B C00E 1.378(3) . ?
C00C H00C 0.9300 . ?
C00C C00J 1.359(3) . ?
N00D C00H 1.360(3) . ?
N00D C00M 1.451(4) . ?
N00D C00N 1.456(3) . ?
C00E H00E 0.9300 . ?
C00E C00K 1.354(3) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.362(3) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.402(3) . ?
C00H C00J 1.410(3) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.383(3) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00M H00D 0.9600 . ?
C00M H00H 0.9600 . ?
C00M H00L 0.9600 . ?
C00N H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?

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
C007 O003 B00L 108.38(15) . . ?
C007 N004 N005 105.02(13) . . ?
N004 N005 B00L 109.38(14) . . ?
C00A N005 N004 121.66(15) . . ?
C00A N005 B00L 128.96(16) . . ?
C008 C006 C007 119.57(15) . . ?
C00I C006 C007 121.42(16) . . ?
C00I C006 C008 118.99(17) . . ?
O003 C007 C006 118.95(15) . . ?
N004 C007 O003 118.89(16) . . ?
N004 C007 C006 122.15(15) . . ?
C006 C008 H008 119.8 . . ?
C00B C008 C006 120.44(17) . . ?
C00B C008 H008 119.8 . . ?
C00C C009 C00A 126.41(16) . . ?
C00C C009 C00F 116.17(18) . . ?
C00F C009 C00A 117.35(18) . . ?
N005 C00A C009 131.02(17) . . ?
N005 C00A H00A 114.5 . . ?
C009 C00A H00A 114.5 . . ?
C008 C00B H00B 120.0 . . ?
C008 C00B C00E 119.96(18) . . ?
C00E C00B H00B 120.0 . . ?
C009 C00C H00C 119.1 . . ?
C00J C00C C009 121.84(18) . . ?
C00J C00C H00C 119.1 . . ?
C00H N00D C00M 121.9(2) . . ?
C00H N00D C00N 120.8(2) . . ?
C00M N00D C00N 117.3(2) . . ?
C00B C00E H00E 120.0 . . ?
C00K C00E C00B 120.03(19) . . ?
C00K C00E H00E 120.0 . . ?
C009 C00F H00F 118.9 . . ?
C00G C00F C009 122.1(2) . . ?
C00G C00F H00F 118.9 . . ?
C00F C00G H00G 119.3 . . ?
C00F C00G C00H 121.41(18) . . ?
C00H C00G H00G 119.3 . . ?
N00D C00H C00G 122.5(2) . . ?
N00D C00H C00J 120.9(2) . . ?
C00G C00H C00J 116.64(19) . . ?
C006 C00I H00I 120.1 . . ?
C006 C00I C00K 119.88(19) . . ?
C00K C00I H00I 120.1 . . ?
C00C C00J C00H 121.8(2) . . ?
C00C C00J H00J 119.1 . . ?
C00H C00J H00J 119.1 . . ?
C00E C00K C00I 120.69(19) . . ?
C00E C00K H00K 119.7 . . ?
C00I C00K H00K 119.7 . . ?
F001 B00L F002 110.31(18) . . ?
F001 B00L O003 112.4(2) . . ?
F001 B00L N005 112.0(2) . . ?
F002 B00L O003 112.0(2) . . ?
F002 B00L N005 111.32(19) . . ?
O003 B00L N005 98.31(14) . . ?
N00D C00M H00D 109.5 . . ?
N00D C00M H00H 109.5 . . ?
N00D C00M H00L 109.5 . . ?
H00D C00M H00H 109.5 . . ?
H00D C00M H00L 109.5 . . ?
H00H C00M H00L 109.5 . . ?
N00D C00N H00M 109.5 . . ?
N00D C00N H00N 109.5 . . ?
N00D C00N H00O 109.5 . . ?
H00M C00N H00N 109.5 . . ?
H00M C00N H00O 109.5 . . ?
H00N C00N H00O 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 1541741'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2f
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 B F2 N2 O'
_chemical_formula_weight         298.09

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   14.090(4)
_cell_length_b                   9.997(3)
_cell_length_c                   20.654(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.333(8)
_cell_angle_gamma                90.00
_cell_volume                     2862.1(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9409
_cell_measurement_theta_min      3.0455
_cell_measurement_theta_max      27.5811

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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-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            42275
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5020
_reflns_number_gt                3292
_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)+(0.0190P)²+52.6910P] 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
_refine_ls_extinction_coef       0.0098(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5020
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2120
_refine_ls_R_factor_gt           0.1725
_refine_ls_wR_factor_ref         0.3908
_refine_ls_wR_factor_gt          0.3726
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
F1 F 0.7176(5) 0.6081(8) 0.0250(4) 0.076(2) Uani 1 1 d . . .
F2 F 0.7109(6) 0.7662(7) 0.1028(4) 0.075(2) Uani 1 1 d . . .
O1 O 0.6866(5) 0.5390(8) 0.1285(4) 0.056(2) Uani 1 1 d . . .
N1 N 0.5238(6) 0.5478(9) 0.0992(4) 0.047(2) Uani 1 1 d . . .
N2 N 0.5607(6) 0.6445(9) 0.0592(4) 0.046(2) Uani 1 1 d . . .
C1 C 0.6735(10) 0.3416(13) 0.2230(6) 0.063(3) Uani 1 1 d . . .
H1 H 0.7337 0.3732 0.2178 0.076 Uiso 1 1 calc R . .
C2 C 0.6702(11) 0.2459(14) 0.2703(7) 0.070(4) Uani 1 1 d . . .
H2 H 0.7263 0.2144 0.2967 0.084 Uiso 1 1 calc R . .
C3 C 0.5801(12) 0.1982(13) 0.2773(6) 0.071(4) Uani 1 1 d . . .
H3 H 0.5760 0.1352 0.3098 0.086 Uiso 1 1 calc R . .
C4 C 0.4953(12) 0.2421(13) 0.2368(7) 0.071(4) Uani 1 1 d . . .
H4 H 0.4358 0.2063 0.2412 0.086 Uiso 1 1 calc R . .
C5 C 0.5016(9) 0.3423(11) 0.1890(6) 0.055(3) Uani 1 1 d . . .
H5 H 0.4466 0.3746 0.1619 0.066 Uiso 1 1 calc R . .
C6 C 0.5961(8) 0.3922(10) 0.1840(5) 0.044(2) Uani 1 1 d . . .
C7 C 0.6013(8) 0.4960(10) 0.1358(5) 0.046(3) Uani 1 1 d . . .
C8 C 0.4961(8) 0.7133(11) 0.0197(5) 0.046(3) Uani 1 1 d . . .
C9 C 0.3929(9) 0.6960(13) 0.0184(6) 0.060(3) Uani 1 1 d . . .
H9A H 0.3771 0.7191 0.0608 0.072 Uiso 1 1 calc R . .
H9B H 0.3745 0.6037 0.0087 0.072 Uiso 1 1 calc R . .
C10 C 0.3396(8) 0.7882(12) -0.0351(6) 0.057(3) Uani 1 1 d . . .
H10A H 0.3006 0.7373 -0.0701 0.068 Uiso 1 1 calc R . .
H10B H 0.2985 0.8507 -0.0171 0.068 Uiso 1 1 calc R . .
C11 C 0.4210(8) 0.8600(11) -0.0594(5) 0.050(3) Uani 1 1 d . . .
C12 C 0.4181(10) 0.9551(12) -0.1088(6) 0.064(3) Uani 1 1 d . . .
H12 H 0.3594 0.9878 -0.1309 0.077 Uiso 1 1 calc R . .
C13 C 0.5050(11) 1.0012(13) -0.1248(6) 0.068(4) Uani 1 1 d . . .
H13 H 0.5039 1.0628 -0.1587 0.082 Uiso 1 1 calc R . .
C14 C 0.5915(10) 0.9559(12) -0.0910(6) 0.062(3) Uani 1 1 d . . .
H14 H 0.6481 0.9902 -0.1017 0.074 Uiso 1 1 calc R . .
C15 C 0.5980(9) 0.8662(12) -0.0440(6) 0.054(3) Uani 1 1 d . . .
H15 H 0.6583 0.8388 -0.0220 0.065 Uiso 1 1 calc R . .
C16 C 0.5127(9) 0.8109(11) -0.0268(5) 0.049(3) Uani 1 1 d . . .
B1 B 0.6762(10) 0.6453(13) 0.0767(7) 0.051(3) Uani 1 1 d . . .
F3 F -0.0011(7) 0.7912(9) 0.5862(4) 0.099(3) Uani 1 1 d . . .
F4 F 0.1582(8) 0.8438(7) 0.5992(4) 0.096(3) Uani 1 1 d . . .
O2 O 0.1124(6) 0.6280(8) 0.6265(4) 0.060(2) Uani 1 1 d . . .
N3 N 0.1224(7) 0.5409(9) 0.5271(4) 0.048(2) Uani 1 1 d . . .
N4 N 0.0971(7) 0.6795(9) 0.5172(4) 0.049(2) Uani 1 1 d . . .
C17 C 0.1734(10) 0.3843(13) 0.6894(6) 0.065(3) Uani 1 1 d . . .
H17 H 0.1620 0.4560 0.7157 0.078 Uiso 1 1 calc R . .
C18 C 0.2083(10) 0.2660(15) 0.7193(7) 0.067(4) Uani 1 1 d . . .
H18 H 0.2226 0.2619 0.7650 0.081 Uiso 1 1 calc R . .
C19 C 0.2219(11) 0.1572(14) 0.6843(8) 0.079(4) Uani 1 1 d . . .
H19 H 0.2417 0.0772 0.7055 0.095 Uiso 1 1 calc R . .
C20 C 0.2057(9) 0.1650(12) 0.6143(7) 0.065(4) Uani 1 1 d . . .
H20 H 0.2165 0.0902 0.5899 0.077 Uiso 1 1 calc R . .
C21 C 0.1734(9) 0.2853(11) 0.5818(6) 0.056(3) Uani 1 1 d . . .
H21 H 0.1644 0.2911 0.5362 0.068 Uiso 1 1 calc R . .
C22 C 0.1546(8) 0.3995(10) 0.6209(5) 0.044(3) Uani 1 1 d . . .
C23 C 0.1296(8) 0.5229(11) 0.5894(6) 0.050(3) Uani 1 1 d . . .
C24 C 0.0856(7) 0.7289(11) 0.4585(5) 0.043(2) Uani 1 1 d . . .
C25 C 0.0911(7) 0.6685(10) 0.3964(5) 0.041(2) Uani 1 1 d . . .
C26 C 0.1083(8) 0.5361(12) 0.3809(6) 0.055(3) Uani 1 1 d . . .
H26 H 0.1202 0.4712 0.4136 0.066 Uiso 1 1 calc R . .
C27 C 0.1073(10) 0.5032(15) 0.3151(7) 0.073(4) Uani 1 1 d . . .
H27 H 0.1170 0.4155 0.3028 0.088 Uiso 1 1 calc R . .
C28 C 0.0910(12) 0.6076(19) 0.2670(7) 0.090(5) Uani 1 1 d . . .
H28 H 0.0936 0.5879 0.2234 0.108 Uiso 1 1 calc R . .
C29 C 0.0719(10) 0.7335(15) 0.2834(6) 0.065(3) Uani 1 1 d . . .
H29 H 0.0566 0.7982 0.2509 0.078 Uiso 1 1 calc R . .
C30 C 0.0751(8) 0.7659(13) 0.3476(6) 0.053(3) Uani 1 1 d . . .
C31 C 0.0629(10) 0.9057(14) 0.3760(7) 0.072(4) Uani 1 1 d . . .
H31A H 0.1145 0.9651 0.3689 0.087 Uiso 1 1 calc R . .
H31B H 0.0015 0.9449 0.3564 0.087 Uiso 1 1 calc R . .
C32 C 0.0674(10) 0.8782(12) 0.4489(6) 0.062(3) Uani 1 1 d . . .
H32A H 0.0071 0.9030 0.4621 0.074 Uiso 1 1 calc R . .
H32B H 0.1192 0.9290 0.4750 0.074 Uiso 1 1 calc R . .
B2 B 0.0855(14) 0.7443(15) 0.5849(7) 0.069(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
F1 B1 1.359(15) . ?
F2 B1 1.376(15) . ?
O1 C7 1.311(13) . ?
O1 B1 1.496(15) . ?
N1 C7 1.317(14) . ?
N1 N2 1.427(12) . ?
N2 C8 1.304(13) . ?
N2 B1 1.603(16) . ?
C1 C6 1.333(16) . ?
C1 C2 1.374(17) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.40(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.420(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.443(16) . ?
C5 H5 0.9300 . ?
C6 C7 1.449(14) . ?
C8 C16 1.416(15) . ?
C8 C9 1.460(16) . ?
C9 C10 1.529(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.514(16) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.390(16) . ?
C11 C16 1.433(16) . ?
C12 C13 1.402(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(18) . ?
C13 H13 0.9300 . ?
C14 C15 1.312(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.425(16) . ?
C15 H15 0.9300 . ?
F3 B2 1.312(19) . ?
F4 B2 1.420(19) . ?
O2 C23 1.347(13) . ?
O2 B2 1.454(17) . ?
N3 C23 1.285(14) . ?
N3 N4 1.436(12) . ?
N4 C24 1.291(13) . ?
N4 B2 1.577(16) . ?
C17 C18 1.383(19) . ?
C17 C22 1.400(16) . ?
C17 H17 0.9300 . ?
C18 C19 1.339(19) . ?
C18 H18 0.9300 . ?
C19 C20 1.425(19) . ?
C19 H19 0.9300 . ?
C20 C21 1.412(17) . ?
C20 H20 0.9300 . ?
C21 C22 1.450(15) . ?
C21 H21 0.9300 . ?
C22 C23 1.410(15) . ?
C24 C25 1.433(14) . ?
C24 C32 1.521(15) . ?
C25 C30 1.391(16) . ?
C25 C26 1.393(15) . ?
C26 C27 1.397(16) . ?
C26 H26 0.9300 . ?
C27 C28 1.43(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.34(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.358(16) . ?
C29 H29 0.9300 . ?
C30 C31 1.537(18) . ?
C31 C32 1.520(18) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?

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
C7 O1 B1 110.0(9) . . ?
C7 N1 N2 104.4(8) . . ?
C8 N2 N1 115.7(9) . . ?
C8 N2 B1 134.8(10) . . ?
N1 N2 B1 109.4(8) . . ?
C6 C1 C2 124.4(13) . . ?
C6 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 117.5(13) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 121.9(13) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 118.9(14) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 117.9(12) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 119.3(11) . . ?
C1 C6 C7 123.4(11) . . ?
C5 C6 C7 117.3(10) . . ?
O1 C7 N1 119.1(9) . . ?
O1 C7 C6 118.3(10) . . ?
N1 C7 C6 122.6(10) . . ?
N2 C8 C16 127.3(10) . . ?
N2 C8 C9 121.9(10) . . ?
C16 C8 C9 110.8(10) . . ?
C8 C9 C10 107.5(10) . . ?
C8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C11 C10 C9 102.8(9) . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
C12 C11 C16 119.0(11) . . ?
C12 C11 C10 130.1(11) . . ?
C16 C11 C10 110.8(10) . . ?
C11 C12 C13 119.1(12) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.4(12) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 122.8(12) . . ?
C15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C14 C15 C16 120.0(12) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C8 C16 C15 133.3(10) . . ?
C8 C16 C11 108.0(10) . . ?
C15 C16 C11 118.6(10) . . ?
F1 B1 F2 112.1(10) . . ?
F1 B1 O1 111.5(10) . . ?
F2 B1 O1 111.2(10) . . ?
F1 B1 N2 112.5(10) . . ?
F2 B1 N2 111.6(10) . . ?
O1 B1 N2 97.0(9) . . ?
C23 O2 B2 110.0(9) . . ?
C23 N3 N4 104.6(9) . . ?
C24 N4 N3 119.3(9) . . ?
C24 N4 B2 131.3(10) . . ?
N3 N4 B2 109.4(9) . . ?
C18 C17 C22 122.1(12) . . ?
C18 C17 H17 118.9 . . ?
C22 C17 H17 118.9 . . ?
C19 C18 C17 121.8(13) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 119.4(13) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.6(12) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 118.7(11) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C17 C22 C23 123.2(10) . . ?
C17 C22 C21 117.2(11) . . ?
C23 C22 C21 119.2(10) . . ?
N3 C23 O2 118.0(10) . . ?
N3 C23 C22 123.6(11) . . ?
O2 C23 C22 118.4(10) . . ?
N4 C24 C25 131.3(10) . . ?
N4 C24 C32 119.3(10) . . ?
C25 C24 C32 109.3(10) . . ?
C30 C25 C26 120.7(10) . . ?
C30 C25 C24 109.0(10) . . ?
C26 C25 C24 130.3(11) . . ?
C25 C26 C27 118.4(12) . . ?
C25 C26 H26 120.8 . . ?
C27 C26 H26 120.8 . . ?
C26 C27 C28 118.4(13) . . ?
C26 C27 H27 120.8 . . ?
C28 C27 H27 120.8 . . ?
C29 C28 C27 121.6(12) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C28 C29 C30 119.8(13) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C29 C30 C25 120.9(12) . . ?
C29 C30 C31 127.1(12) . . ?
C25 C30 C31 112.0(10) . . ?
C32 C31 C30 103.0(10) . . ?
C32 C31 H31A 111.2 . . ?
C30 C31 H31A 111.2 . . ?
C32 C31 H31B 111.2 . . ?
C30 C31 H31B 111.2 . . ?
H31A C31 H31B 109.1 . . ?
C31 C32 C24 106.5(10) . . ?
C31 C32 H32A 110.4 . . ?
C24 C32 H32A 110.4 . . ?
C31 C32 H32B 110.4 . . ?
C24 C32 H32B 110.4 . . ?
H32A C32 H32B 108.6 . . ?
F3 B2 F4 112.6(12) . . ?
F3 B2 O2 114.8(14) . . ?
F4 B2 O2 109.7(13) . . ?
F3 B2 N4 114.1(13) . . ?
F4 B2 N4 106.6(12) . . ?
O2 B2 N4 97.9(10) . . ?

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
C7 N1 N2 C8 -177.8(9) . . . . ?
C7 N1 N2 B1 0.1(11) . . . . ?
C6 C1 C2 C3 1(2) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C2 C3 C4 C5 -2.6(19) . . . . ?
C3 C4 C5 C6 1.0(16) . . . . ?
C2 C1 C6 C5 -2.2(19) . . . . ?
C2 C1 C6 C7 178.0(12) . . . . ?
C4 C5 C6 C1 1.2(16) . . . . ?
C4 C5 C6 C7 -178.9(10) . . . . ?
B1 O1 C7 N1 0.4(13) . . . . ?
B1 O1 C7 C6 180.0(9) . . . . ?
N2 N1 C7 O1 -0.3(12) . . . . ?
N2 N1 C7 C6 -179.9(9) . . . . ?
C1 C6 C7 O1 2.6(16) . . . . ?
C5 C6 C7 O1 -177.2(9) . . . . ?
C1 C6 C7 N1 -177.8(11) . . . . ?
C5 C6 C7 N1 2.4(15) . . . . ?
N1 N2 C8 C16 -177.3(9) . . . . ?
B1 N2 C8 C16 5.5(19) . . . . ?
N1 N2 C8 C9 2.4(14) . . . . ?
B1 N2 C8 C9 -174.8(11) . . . . ?
N2 C8 C9 C10 -178.0(10) . . . . ?
C16 C8 C9 C10 1.8(12) . . . . ?
C8 C9 C10 C11 -2.7(12) . . . . ?
C9 C10 C11 C12 178.8(11) . . . . ?
C9 C10 C11 C16 2.9(12) . . . . ?
C16 C11 C12 C13 -0.6(17) . . . . ?
C10 C11 C12 C13 -176.2(11) . . . . ?
C11 C12 C13 C14 -1.9(19) . . . . ?
C12 C13 C14 C15 2(2) . . . . ?
C13 C14 C15 C16 0.5(19) . . . . ?
N2 C8 C16 C15 -1.8(19) . . . . ?
C9 C8 C16 C15 178.5(12) . . . . ?
N2 C8 C16 C11 179.8(10) . . . . ?
C9 C8 C16 C11 0.1(12) . . . . ?
C14 C15 C16 C8 178.8(11) . . . . ?
C14 C15 C16 C11 -3.0(16) . . . . ?
C12 C11 C16 C8 -178.4(10) . . . . ?
C10 C11 C16 C8 -2.0(12) . . . . ?
C12 C11 C16 C15 3.0(15) . . . . ?
C10 C11 C16 C15 179.4(10) . . . . ?
C7 O1 B1 F1 -117.8(11) . . . . ?
C7 O1 B1 F2 116.2(11) . . . . ?
C7 O1 B1 N2 -0.2(11) . . . . ?
C8 N2 B1 F1 -65.8(16) . . . . ?
N1 N2 B1 F1 116.9(10) . . . . ?
C8 N2 B1 F2 61.2(16) . . . . ?
N1 N2 B1 F2 -116.1(10) . . . . ?
C8 N2 B1 O1 177.4(11) . . . . ?
N1 N2 B1 O1 0.0(10) . . . . ?
C23 N3 N4 C24 179.3(10) . . . . ?
C23 N3 N4 B2 -2.3(13) . . . . ?
C22 C17 C18 C19 -3(2) . . . . ?
C17 C18 C19 C20 4(2) . . . . ?
C18 C19 C20 C21 -1(2) . . . . ?
C19 C20 C21 C22 -1.7(18) . . . . ?
C18 C17 C22 C23 -172.5(12) . . . . ?
C18 C17 C22 C21 -0.2(18) . . . . ?
C20 C21 C22 C17 2.4(16) . . . . ?
C20 C21 C22 C23 175.1(10) . . . . ?
N4 N3 C23 O2 0.6(13) . . . . ?
N4 N3 C23 C22 -179.4(10) . . . . ?
B2 O2 C23 N3 1.6(15) . . . . ?
B2 O2 C23 C22 -178.5(11) . . . . ?
C17 C22 C23 N3 172.2(11) . . . . ?
C21 C22 C23 N3 0.0(16) . . . . ?
C17 C22 C23 O2 -7.7(16) . . . . ?
C21 C22 C23 O2 -179.9(10) . . . . ?
N3 N4 C24 C25 1.8(17) . . . . ?
B2 N4 C24 C25 -176.2(13) . . . . ?
N3 N4 C24 C32 -174.7(10) . . . . ?
B2 N4 C24 C32 7.3(19) . . . . ?
N4 C24 C25 C30 -178.6(11) . . . . ?
C32 C24 C25 C30 -1.8(12) . . . . ?
N4 C24 C25 C26 1.9(19) . . . . ?
C32 C24 C25 C26 178.7(11) . . . . ?
C30 C25 C26 C27 -1.2(16) . . . . ?
C24 C25 C26 C27 178.3(11) . . . . ?
C25 C26 C27 C28 1.5(19) . . . . ?
C26 C27 C28 C29 -3(2) . . . . ?
C27 C28 C29 C30 5(2) . . . . ?
C28 C29 C30 C25 -4.6(19) . . . . ?
C28 C29 C30 C31 175.1(13) . . . . ?
C26 C25 C30 C29 2.7(16) . . . . ?
C24 C25 C30 C29 -176.9(10) . . . . ?
C26 C25 C30 C31 -177.0(10) . . . . ?
C24 C25 C30 C31 3.4(13) . . . . ?
C29 C30 C31 C32 176.8(12) . . . . ?
C25 C30 C31 C32 -3.5(13) . . . . ?
C30 C31 C32 C24 2.2(13) . . . . ?
N4 C24 C32 C31 176.8(10) . . . . ?
C25 C24 C32 C31 -0.4(13) . . . . ?
C23 O2 B2 F3 118.6(12) . . . . ?
C23 O2 B2 F4 -113.5(11) . . . . ?
C23 O2 B2 N4 -2.6(14) . . . . ?
C24 N4 B2 F3 59.4(19) . . . . ?
N3 N4 B2 F3 -118.8(12) . . . . ?
C24 N4 B2 F4 -65.5(18) . . . . ?
N3 N4 B2 F4 116.3(11) . . . . ?
C24 N4 B2 O2 -178.8(11) . . . . ?
N3 N4 B2 O2 3.0(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.127
####################################################################### 
# 
# 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_mo_20180526a_0m
_database_code_depnum_ccdc_archive 'CCDC 1873750'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;
_audit_creation_date             2018-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_name_common            ?
_chemical_name_systematic        3
_chemical_formula_moiety         'C15 H13 B F2 N2 O2'
_chemical_formula_sum            'C15 H13 B F2 N2 O2'
_chemical_formula_weight         302.08
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1278(7)
_cell_length_b                   9.0511(7)
_cell_length_c                   10.3004(8)
_cell_angle_alpha                82.101(3)
_cell_angle_beta                 84.055(3)
_cell_angle_gamma                70.628(3)
_cell_volume                     706.71(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.68
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0581 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.9321.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             312
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18925
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.791
_diffrn_reflns_theta_min         2.951
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2788
_reflns_number_total             3248
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.1680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1165
_refine_special_details          ?
_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:
 C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00L(H00C,H00L,H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O001 O 0.32703(13) 0.22324(10) 0.60875(9) 0.0517(3) Uani 1 1 d . . . . .
F002 F 0.27732(15) 0.21266(12) 0.83867(9) 0.0802(3) Uani 1 1 d . . . . .
F003 F 0.07731(14) 0.17645(11) 0.72065(11) 0.0798(3) Uani 1 1 d . . . . .
N004 N 0.11455(14) 0.43503(12) 0.69012(10) 0.0423(2) Uani 1 1 d . . . . .
O005 O 0.72889(15) 0.35222(14) 0.06791(10) 0.0624(3) Uani 1 1 d . . . . .
N006 N 0.18821(13) 0.48674(12) 0.57146(9) 0.0403(2) Uani 1 1 d . . . . .
C007 C 0.41875(15) 0.35807(14) 0.41433(11) 0.0381(3) Uani 1 1 d . . . . .
C008 C 0.30640(15) 0.35879(14) 0.53435(11) 0.0387(3) Uani 1 1 d . . . . .
C009 C -0.09320(15) 0.69414(15) 0.74529(12) 0.0415(3) Uani 1 1 d . . . . .
C00A C 0.40494(17) 0.49559(15) 0.32920(12) 0.0438(3) Uani 1 1 d . . . . .
H00A H 0.3244 0.5910 0.3497 0.053 Uiso 1 1 calc R . . . .
C00B C -0.06545(17) 0.79646(16) 0.63762(14) 0.0484(3) Uani 1 1 d . . . . .
H00B H 0.0162 0.7585 0.5698 0.058 Uiso 1 1 calc R . . . .
C00C C 0.63141(16) 0.34730(16) 0.18365(12) 0.0445(3) Uani 1 1 d . . . . .
C00D C -0.00469(17) 0.52614(15) 0.76245(12) 0.0444(3) Uani 1 1 d . . . . .
H00D H -0.0399 0.4746 0.8392 0.053 Uiso 1 1 calc R . . . .
C00E C 0.54080(17) 0.21712(15) 0.38216(12) 0.0452(3) Uani 1 1 d . . . . .
H00E H 0.5508 0.1254 0.4384 0.054 Uiso 1 1 calc R . . . .
C00F C 0.51044(18) 0.48987(16) 0.21507(13) 0.0481(3) Uani 1 1 d . . . . .
H00F H 0.5009 0.5815 0.1587 0.058 Uiso 1 1 calc R . . . .
C00G C -0.21775(18) 0.75383(18) 0.84631(13) 0.0514(3) Uani 1 1 d . . . . .
H00G H -0.2375 0.6863 0.9183 0.062 Uiso 1 1 calc R . . . .
C00H C 0.64800(17) 0.21063(16) 0.26785(13) 0.0472(3) Uani 1 1 d . . . . .
H00H H 0.7300 0.1157 0.2479 0.057 Uiso 1 1 calc R . . . .
C00I C -0.3108(2) 0.9125(2) 0.83894(16) 0.0614(4) Uani 1 1 d . . . . .
H00I H -0.3931 0.9517 0.9060 0.074 Uiso 1 1 calc R . . . .
C00J C -0.1605(2) 0.95487(18) 0.63272(17) 0.0602(4) Uani 1 1 d . . . . .
H00J H -0.1424 1.0237 0.5611 0.072 Uiso 1 1 calc R . . . .
C00K C -0.2823(2) 1.01232(18) 0.73329(18) 0.0629(4) Uani 1 1 d . . . . .
H00K H -0.3451 1.1193 0.7289 0.075 Uiso 1 1 calc R . . . .
C00L C 0.8314(3) 0.2055(2) 0.02344(18) 0.0742(5) Uani 1 1 d . . . . .
H00C H 0.8825 0.2236 -0.0631 0.111 Uiso 1 1 calc GR . . . .
H00L H 0.7586 0.1415 0.0211 0.111 Uiso 1 1 calc GR . . . .
H00M H 0.9224 0.1525 0.0822 0.111 Uiso 1 1 calc GR . . . .
B00M B 0.1998(2) 0.24956(18) 0.72193(15) 0.0525(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
O001 C008 1.3238(15) . ?
O001 B00M 1.4658(17) . ?
F002 B00M 1.364(2) . ?
F003 B00M 1.368(2) . ?
N004 N006 1.3959(13) . ?
N004 C00D 1.2898(16) . ?
N004 B00M 1.5905(18) . ?
O005 C00C 1.3653(15) . ?
O005 C00L 1.422(2) . ?
N006 C008 1.3106(15) . ?
C007 C008 1.4583(16) . ?
C007 C00A 1.3995(17) . ?
C007 C00E 1.3892(17) . ?
C009 C00B 1.3939(18) . ?
C009 C00D 1.4449(18) . ?
C009 C00G 1.4046(17) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.3778(18) . ?
C00B H00B 0.9300 . ?
C00B C00J 1.381(2) . ?
C00C C00F 1.3942(19) . ?
C00C C00H 1.3854(19) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00H 1.3862(17) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00I 1.379(2) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00K 1.368(2) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.385(2) . ?
C00K H00K 0.9300 . ?
C00L H00C 0.9600 . ?
C00L H00L 0.9600 . ?
C00L H00M 0.9600 . ?

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
C008 O001 B00M 108.90(10) . . ?
N006 N004 B00M 110.06(9) . . ?
C00D N004 N006 124.25(11) . . ?
C00D N004 B00M 125.69(11) . . ?
C00C O005 C00L 117.12(12) . . ?
C008 N006 N004 104.05(9) . . ?
C00A C007 C008 121.67(11) . . ?
C00E C007 C008 119.38(11) . . ?
C00E C007 C00A 118.94(11) . . ?
O001 C008 C007 117.77(10) . . ?
N006 C008 O001 119.17(10) . . ?
N006 C008 C007 123.05(11) . . ?
C00B C009 C00D 125.13(11) . . ?
C00B C009 C00G 119.42(12) . . ?
C00G C009 C00D 115.44(12) . . ?
C007 C00A H00A 120.0 . . ?
C00F C00A C007 120.10(12) . . ?
C00F C00A H00A 120.0 . . ?
C009 C00B H00B 120.4 . . ?
C00J C00B C009 119.30(13) . . ?
C00J C00B H00B 120.4 . . ?
O005 C00C C00F 116.33(12) . . ?
O005 C00C C00H 123.46(12) . . ?
C00H C00C C00F 120.21(11) . . ?
N004 C00D C009 131.37(12) . . ?
N004 C00D H00D 114.3 . . ?
C009 C00D H00D 114.3 . . ?
C007 C00E H00E 119.4 . . ?
C00H C00E C007 121.27(12) . . ?
C00H C00E H00E 119.4 . . ?
C00A C00F C00C 120.29(12) . . ?
C00A C00F H00F 119.9 . . ?
C00C C00F H00F 119.9 . . ?
C009 C00G H00G 120.0 . . ?
C00I C00G C009 120.08(14) . . ?
C00I C00G H00G 120.0 . . ?
C00C C00H C00E 119.18(12) . . ?
C00C C00H H00H 120.4 . . ?
C00E C00H H00H 120.4 . . ?
C00G C00I H00I 119.9 . . ?
C00K C00I C00G 120.18(14) . . ?
C00K C00I H00I 119.9 . . ?
C00B C00J H00J 119.7 . . ?
C00B C00J C00K 120.70(15) . . ?
C00K C00J H00J 119.7 . . ?
C00I C00K C00J 120.31(14) . . ?
C00I C00K H00K 119.8 . . ?
C00J C00K H00K 119.8 . . ?
O005 C00L H00C 109.5 . . ?
O005 C00L H00L 109.5 . . ?
O005 C00L H00M 109.5 . . ?
H00C C00L H00L 109.5 . . ?
H00C C00L H00M 109.5 . . ?
H00L C00L H00M 109.5 . . ?
O001 B00M N004 97.72(10) . . ?
F002 B00M O001 112.58(14) . . ?
F002 B00M F003 111.50(13) . . ?
F002 B00M N004 111.03(12) . . ?
F003 B00M O001 112.89(12) . . ?
F003 B00M N004 110.38(13) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_pl
_database_code_depnum_ccdc_archive 'CCDC 1873751'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;
_audit_creation_date             2018-10-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        4e
_chemical_formula_moiety         'C16 H15 B Br F2 N3 O'
_chemical_formula_sum            'C16 H15 B Br F2 N3 O'
_chemical_formula_weight         394.03
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.3547(5)
_cell_length_b                   25.1921(15)
_cell_length_c                   9.1335(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.823(2)
_cell_angle_gamma                90
_cell_volume                     1619.83(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9370
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.11
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.567
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1210 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.7135.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            68284
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_min         2.893
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2562
_reflns_number_total             3738
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0205P)²+2.9494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1093
_refine_special_details          ?
_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:
 C00K(H00K), C00O(H00O), C00P(H00P), C00S(H00S), C00V(H00V), C00Y(H00Y),
 C00Z(H00Z), C012(H012), C015(H015)
2.b Idealised Me refined as rotating group:
 C019(H01A,H01B,H01C), C01A(H01D,H01E,H01F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br01 Br 0.42286(8) -0.23822(2) 0.65949(5) 0.06376(18) Uani 1 1 d . . . . .
F004 F 0.8623(4) -0.16689(9) 1.1600(3) 0.0667(7) Uani 1 1 d . . . . .
F005 F 0.5872(4) -0.14332(10) 1.2044(3) 0.0712(8) Uani 1 1 d . . . . .
O008 O 0.8167(4) -0.07738(10) 1.2143(3) 0.0503(7) Uani 1 1 d . . . . .
N009 N 0.6494(4) -0.10786(11) 0.9765(3) 0.0373(7) Uani 1 1 d . . . . .
N00A N 0.6847(4) -0.05424(11) 0.9661(3) 0.0360(7) Uani 1 1 d . . . . .
N00D N 1.0611(5) 0.16547(12) 1.2779(3) 0.0452(8) Uani 1 1 d . . . . .
C00F C 0.8523(5) 0.01249(13) 1.1473(4) 0.0339(8) Uani 1 1 d . . . . .
C00H C 0.7816(5) -0.04033(13) 1.1059(4) 0.0362(8) Uani 1 1 d . . . . .
C00I C 0.4740(5) -0.12486(14) 0.7042(4) 0.0359(8) Uani 1 1 d . . . . .
C00K C 1.0330(5) 0.07316(14) 1.3395(4) 0.0402(9) Uani 1 1 d . . . . .
H00K H 1.1070 0.0789 1.4396 0.048 Uiso 1 1 calc R . . . .
C00L C 0.3969(5) -0.16555(14) 0.5999(4) 0.0385(8) Uani 1 1 d . . . . .
C00O C 0.8113(6) 0.05440(14) 1.0433(4) 0.0400(9) Uani 1 1 d . . . . .
H00O H 0.7364 0.0482 0.9437 0.048 Uiso 1 1 calc R . . . .
C00P C 0.8791(6) 0.10441(14) 1.0847(4) 0.0413(9) Uani 1 1 d . . . . .
H00P H 0.8497 0.1316 1.0127 0.050 Uiso 1 1 calc R . . . .
C00Q C 0.9935(5) 0.11571(13) 1.2355(4) 0.0358(8) Uani 1 1 d . . . . .
C00S C 0.9638(5) 0.02324(14) 1.2954(4) 0.0399(9) Uani 1 1 d . . . . .
H00S H 0.9924 -0.0042 1.3666 0.048 Uiso 1 1 calc R . . . .
C00V C 0.5593(5) -0.13770(14) 0.8634(4) 0.0395(9) Uani 1 1 d . . . . .
H00V H 0.5477 -0.1730 0.8887 0.047 Uiso 1 1 calc R . . . .
C00Y C 0.4575(6) -0.07306(15) 0.6462(4) 0.0429(9) Uani 1 1 d . . . . .
H00Y H 0.5084 -0.0450 0.7114 0.052 Uiso 1 1 calc R . . . .
C00Z C 0.3045(6) -0.15503(17) 0.4475(4) 0.0492(10) Uani 1 1 d . . . . .
H00Z H 0.2531 -0.1825 0.3802 0.059 Uiso 1 1 calc R . . . .
C012 C 0.2902(6) -0.10349(17) 0.3977(4) 0.0499(10) Uani 1 1 d . . . . .
H012 H 0.2269 -0.0961 0.2959 0.060 Uiso 1 1 calc R . . . .
C015 C 0.3667(6) -0.06292(17) 0.4939(4) 0.0533(11) Uani 1 1 d . . . . .
H015 H 0.3579 -0.0283 0.4572 0.064 Uiso 1 1 calc R . . . .
C019 C 1.0112(7) 0.20931(15) 1.1731(5) 0.0613(12) Uani 1 1 d . . . . .
H01A H 0.8761 0.2146 1.1443 0.092 Uiso 1 1 calc GR . . . .
H01B H 1.0500 0.2018 1.0836 0.092 Uiso 1 1 calc GR . . . .
H01C H 1.0740 0.2408 1.2214 0.092 Uiso 1 1 calc GR . . . .
C01A C 1.1465(6) 0.17784(16) 1.4392(4) 0.0514(10) Uani 1 1 d . . . . .
H01D H 1.2573 0.1562 1.4792 0.077 Uiso 1 1 calc GR . . . .
H01E H 1.0566 0.1708 1.4948 0.077 Uiso 1 1 calc GR . . . .
H01F H 1.1819 0.2146 1.4498 0.077 Uiso 1 1 calc GR . . . .
B01B B 0.7321(8) -0.12762(18) 1.1483(5) 0.0482(12) 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
Br01 C00L 1.904(4) . ?
F004 B01B 1.359(6) . ?
F005 B01B 1.368(6) . ?
O008 C00H 1.331(4) . ?
O008 B01B 1.461(5) . ?
N009 N00A 1.384(4) . ?
N009 C00V 1.295(4) . ?
N009 B01B 1.590(5) . ?
N00A C00H 1.317(4) . ?
N00D C00Q 1.363(4) . ?
N00D C019 1.438(5) . ?
N00D C01A 1.458(5) . ?
C00F C00H 1.439(5) . ?
C00F C00O 1.394(5) . ?
C00F C00S 1.391(4) . ?
C00I C00L 1.402(5) . ?
C00I C00V 1.444(5) . ?
C00I C00Y 1.400(5) . ?
C00K H00K 0.9300 . ?
C00K C00Q 1.406(5) . ?
C00K C00S 1.372(5) . ?
C00L C00Z 1.387(5) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.367(5) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.420(5) . ?
C00S H00S 0.9300 . ?
C00V H00V 0.9300 . ?
C00Y H00Y 0.9300 . ?
C00Y C015 1.382(5) . ?
C00Z H00Z 0.9300 . ?
C00Z C012 1.370(6) . ?
C012 H012 0.9300 . ?
C012 C015 1.359(6) . ?
C015 H015 0.9300 . ?
C019 H01A 0.9600 . ?
C019 H01B 0.9600 . ?
C019 H01C 0.9600 . ?
C01A H01D 0.9600 . ?
C01A H01E 0.9600 . ?
C01A H01F 0.9600 . ?

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
C00H O008 B01B 109.4(3) . . ?
N00A N009 B01B 110.3(3) . . ?
C00V N009 N00A 125.1(3) . . ?
C00V N009 B01B 124.6(3) . . ?
C00H N00A N009 104.6(3) . . ?
C00Q N00D C019 121.0(3) . . ?
C00Q N00D C01A 119.9(3) . . ?
C019 N00D C01A 117.4(3) . . ?
C00O C00F C00H 122.1(3) . . ?
C00S C00F C00H 120.2(3) . . ?
C00S C00F C00O 117.8(3) . . ?
O008 C00H C00F 118.4(3) . . ?
N00A C00H O008 118.0(3) . . ?
N00A C00H C00F 123.6(3) . . ?
C00L C00I C00V 119.5(3) . . ?
C00Y C00I C00L 116.8(3) . . ?
C00Y C00I C00V 123.7(3) . . ?
C00Q C00K H00K 119.5 . . ?
C00S C00K H00K 119.5 . . ?
C00S C00K C00Q 120.9(3) . . ?
C00I C00L Br01 121.4(3) . . ?
C00Z C00L Br01 116.8(3) . . ?
C00Z C00L C00I 121.8(3) . . ?
C00F C00O H00O 119.3 . . ?
C00P C00O C00F 121.3(3) . . ?
C00P C00O H00O 119.3 . . ?
C00O C00P H00P 119.4 . . ?
C00O C00P C00Q 121.3(3) . . ?
C00Q C00P H00P 119.4 . . ?
N00D C00Q C00K 121.5(3) . . ?
N00D C00Q C00P 121.7(3) . . ?
C00K C00Q C00P 116.8(3) . . ?
C00F C00S H00S 119.1 . . ?
C00K C00S C00F 121.9(3) . . ?
C00K C00S H00S 119.1 . . ?
N009 C00V C00I 130.3(3) . . ?
N009 C00V H00V 114.9 . . ?
C00I C00V H00V 114.9 . . ?
C00I C00Y H00Y 119.4 . . ?
C015 C00Y C00I 121.1(4) . . ?
C015 C00Y H00Y 119.4 . . ?
C00L C00Z H00Z 120.6 . . ?
C012 C00Z C00L 118.9(4) . . ?
C012 C00Z H00Z 120.6 . . ?
C00Z C012 H012 119.3 . . ?
C015 C012 C00Z 121.3(4) . . ?
C015 C012 H012 119.3 . . ?
C00Y C015 H015 120.0 . . ?
C012 C015 C00Y 120.1(4) . . ?
C012 C015 H015 120.0 . . ?
N00D C019 H01A 109.5 . . ?
N00D C019 H01B 109.5 . . ?
N00D C019 H01C 109.5 . . ?
H01A C019 H01B 109.5 . . ?
H01A C019 H01C 109.5 . . ?
H01B C019 H01C 109.5 . . ?
N00D C01A H01D 109.5 . . ?
N00D C01A H01E 109.5 . . ?
N00D C01A H01F 109.5 . . ?
H01D C01A H01E 109.5 . . ?
H01D C01A H01F 109.5 . . ?
H01E C01A H01F 109.5 . . ?
F004 B01B F005 111.6(4) . . ?
F004 B01B O008 113.1(4) . . ?
F004 B01B N009 111.4(3) . . ?
F005 B01B O008 112.4(4) . . ?
F005 B01B N009 110.1(4) . . ?
O008 B01B N009 97.6(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
Br01 C00L C00Z C012 -177.0(3) . . . . ?
N009 N00A C00H O008 -1.0(4) . . . . ?
N009 N00A C00H C00F 178.6(3) . . . . ?
N00A N009 C00V C00I -0.3(6) . . . . ?
N00A N009 B01B F004 -120.8(3) . . . . ?
N00A N009 B01B F005 114.9(3) . . . . ?
N00A N009 B01B O008 -2.3(4) . . . . ?
C00F C00O C00P C00Q -0.2(6) . . . . ?
C00H O008 B01B F004 118.9(4) . . . . ?
C00H O008 B01B F005 -113.7(4) . . . . ?
C00H O008 B01B N009 1.7(4) . . . . ?
C00H C00F C00O C00P 179.8(4) . . . . ?
C00H C00F C00S C00K -179.6(4) . . . . ?
C00I C00L C00Z C012 0.7(6) . . . . ?
C00I C00Y C015 C012 0.5(6) . . . . ?
C00L C00I C00V N009 174.7(4) . . . . ?
C00L C00I C00Y C015 1.0(6) . . . . ?
C00L C00Z C012 C015 0.9(6) . . . . ?
C00O C00F C00H O008 -175.7(3) . . . . ?
C00O C00F C00H N00A 4.7(6) . . . . ?
C00O C00F C00S C00K -0.2(6) . . . . ?
C00O C00P C00Q N00D -179.7(4) . . . . ?
C00O C00P C00Q C00K -0.1(6) . . . . ?
C00Q C00K C00S C00F -0.1(6) . . . . ?
C00S C00F C00H O008 3.7(5) . . . . ?
C00S C00F C00H N00A -175.9(3) . . . . ?
C00S C00F C00O C00P 0.4(6) . . . . ?
C00S C00K C00Q N00D 179.9(4) . . . . ?
C00S C00K C00Q C00P 0.3(6) . . . . ?
C00V N009 N00A C00H -178.9(4) . . . . ?
C00V N009 B01B F004 60.2(5) . . . . ?
C00V N009 B01B F005 -64.1(5) . . . . ?
C00V N009 B01B O008 178.7(3) . . . . ?
C00V C00I C00L Br01 -5.9(5) . . . . ?
C00V C00I C00L C00Z 176.5(4) . . . . ?
C00V C00I C00Y C015 -177.0(4) . . . . ?
C00Y C00I C00L Br01 176.0(3) . . . . ?
C00Y C00I C00L C00Z -1.5(6) . . . . ?
C00Y C00I C00V N009 -7.3(7) . . . . ?
C00Z C012 C015 C00Y -1.5(7) . . . . ?
C019 N00D C00Q C00K -176.5(4) . . . . ?
C019 N00D C00Q C00P 3.1(6) . . . . ?
C01A N00D C00Q C00K -11.3(6) . . . . ?
C01A N00D C00Q C00P 168.3(4) . . . . ?
B01B O008 C00H N00A -0.6(5) . . . . ?
B01B O008 C00H C00F 179.7(4) . . . . ?
B01B N009 N00A C00H 2.1(4) . . . . ?
B01B N009 C00V C00I 178.5(4) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
