# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mcg16174
_database_code_depnum_ccdc_archive 'CCDC 1531825'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;
_audit_creation_date             2017-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            (AN2690)(ina)
_chemical_name_systematic        
'5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole, isonicotinamide'
_chemical_formula_moiety         'C7 H6 B F O2, C6 H6 N2 O'
_chemical_formula_sum            'C13 H12 B F N2 O3'
_chemical_formula_weight         274.06
_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                   15.8870(16)
_cell_length_b                   5.9848(6)
_cell_length_c                   13.8225(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.469(5)
_cell_angle_gamma                90
_cell_volume                     1311.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4580
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      1.00
_cell_measurement_theta_min      25.35
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.9502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method 
'Slow evaporation of a methanol solution containing 1 equivalent of insonicotinamide and 1 equivalent of AN2690'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7571
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.363
_diffrn_reflns_theta_max         25.363
_diffrn_reflns_theta_min         2.569
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1614
_reflns_number_total             2398
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.069
_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)+(0.0660P)²+0.1740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1346
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C6(H6), C5(H5), C9(H9), C12(H12), C3(H3), C8(H8)
2.c X=CH2 refined with riding coordinates:
 N2(H2a,H2b)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2 O 0.72614(10) 0.3622(2) 0.84053(10) 0.0716(5) Uani 1 1 d . . . . .
H2 H 0.7210 0.4292 0.7888 0.107 Uiso 1 1 calc GR . . . .
O1 O 0.79374(10) 0.0496(2) 0.91059(10) 0.0735(5) Uani 1 1 d . . . . .
F1 F 0.98668(9) -0.2560(3) 0.58095(10) 0.1027(5) Uani 1 1 d . . . . .
O3 O 0.50703(10) 1.3176(3) 0.60098(11) 0.0804(5) Uani 1 1 d . . . . .
N1 N 0.68290(10) 0.6541(3) 0.69639(12) 0.0602(5) Uani 1 1 d . . . . .
N2 N 0.58427(11) 1.2906(3) 0.47126(12) 0.0678(5) Uani 1 1 d . . . . .
H2A H 0.5595 1.4040 0.4439 0.081 Uiso 1 1 calc R . . . .
H2B H 0.6232 1.2213 0.4427 0.081 Uiso 1 1 calc R . . . .
C10 C 0.60639(12) 1.0239(3) 0.60342(13) 0.0524(5) Uani 1 1 d . . . . .
C1 C 0.83200(12) 0.1055(3) 0.74883(13) 0.0523(5) Uani 1 1 d . . . . .
C2 C 0.87230(12) -0.0863(3) 0.78445(14) 0.0568(5) Uani 1 1 d . . . . .
C11 C 0.66181(13) 0.8889(3) 0.55804(15) 0.0605(5) Uani 1 1 d . . . . .
H11 H 0.6748 0.9199 0.4947 0.073 Uiso 1 1 calc R . . . .
C13 C 0.56245(12) 1.2229(3) 0.55751(14) 0.0570(5) Uani 1 1 d . . . . .
C6 C 0.84523(13) 0.1729(4) 0.65460(14) 0.0607(5) Uani 1 1 d . . . . .
H6 H 0.8189 0.3009 0.6295 0.073 Uiso 1 1 calc R . . . .
C5 C 0.89732(14) 0.0505(4) 0.59813(15) 0.0688(6) Uani 1 1 d . . . . .
H5 H 0.9067 0.0948 0.5352 0.083 Uiso 1 1 calc R . . . .
C9 C 0.58961(14) 0.9682(4) 0.69680(15) 0.0676(6) Uani 1 1 d . . . . .
H9 H 0.5524 1.0540 0.7306 0.081 Uiso 1 1 calc R . . . .
C12 C 0.69819(14) 0.7080(3) 0.60575(14) 0.0630(6) Uani 1 1 d . . . . .
H12 H 0.7352 0.6193 0.5731 0.076 Uiso 1 1 calc R . . . .
C4 C 0.93479(13) -0.1377(4) 0.63714(16) 0.0689(6) Uani 1 1 d . . . . .
C7 C 0.85060(16) -0.1267(4) 0.88717(16) 0.0725(6) Uani 1 1 d . . . . .
H7A H 0.8238 -0.2713 0.8931 0.087 Uiso 1 1 calc R . . . .
H7B H 0.9010 -0.1228 0.9304 0.087 Uiso 1 1 calc R . . . .
C3 C 0.92438(13) -0.2125(4) 0.72895(16) 0.0666(6) Uani 1 1 d . . . . .
H3 H 0.9508 -0.3413 0.7530 0.080 Uiso 1 1 calc R . . . .
C8 C 0.62846(14) 0.7838(4) 0.74017(15) 0.0711(6) Uani 1 1 d . . . . .
H8 H 0.6160 0.7484 0.8032 0.085 Uiso 1 1 calc R . . . .
B1 B 0.77941(16) 0.1902(4) 0.83246(16) 0.0585(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
O2 H2 0.8200 . ?
O2 B1 1.341(3) . ?
O1 C7 1.438(3) . ?
O1 B1 1.377(3) . ?
F1 C4 1.364(2) . ?
O3 C13 1.233(2) . ?
N1 C12 1.330(2) . ?
N1 C8 1.334(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C13 1.325(2) . ?
C10 C11 1.374(3) . ?
C10 C13 1.502(3) . ?
C10 C9 1.375(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.392(3) . ?
C1 B1 1.552(3) . ?
C2 C7 1.501(3) . ?
C2 C3 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.369(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.383(3) . ?
C12 H12 0.9300 . ?
C4 C3 1.365(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C3 H3 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O2 H2 109.5 . . ?
B1 O1 C7 110.36(16) . . ?
C12 N1 C8 116.50(17) . . ?
H2A N2 H2B 120.0 . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
C11 C10 C13 124.60(17) . . ?
C11 C10 C9 116.89(18) . . ?
C9 C10 C13 118.50(18) . . ?
C2 C1 C6 118.58(18) . . ?
C2 C1 B1 105.27(17) . . ?
C6 C1 B1 136.15(19) . . ?
C1 C2 C7 109.92(18) . . ?
C3 C2 C1 122.12(19) . . ?
C3 C2 C7 127.96(19) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.38(18) . . ?
C12 C11 H11 119.8 . . ?
O3 C13 N2 122.09(18) . . ?
O3 C13 C10 119.06(17) . . ?
N2 C13 C10 118.85(17) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.31(19) . . ?
C5 C6 H6 119.8 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.34(19) . . ?
C4 C5 H5 120.8 . . ?
C10 C9 H9 120.2 . . ?
C10 C9 C8 119.55(19) . . ?
C8 C9 H9 120.2 . . ?
N1 C12 C11 123.15(18) . . ?
N1 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
F1 C4 C5 117.8(2) . . ?
F1 C4 C3 118.1(2) . . ?
C3 C4 C5 124.1(2) . . ?
O1 C7 C2 106.15(16) . . ?
O1 C7 H7A 110.5 . . ?
O1 C7 H7B 110.5 . . ?
C2 C7 H7A 110.5 . . ?
C2 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C2 C3 H3 121.7 . . ?
C4 C3 C2 116.5(2) . . ?
C4 C3 H3 121.7 . . ?
N1 C8 C9 123.52(19) . . ?
N1 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
O2 B1 O1 118.62(19) . . ?
O2 B1 C1 133.11(19) . . ?
O1 B1 C1 108.27(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.82 1.93 2.707(2) 158.5 .
N2 H2A O3 0.86 2.05 2.902(2) 171.1 3_686
N2 H2B O2 0.86 2.28 3.110(2) 162.3 4_575
C5 H5 F1 0.93 2.59 3.404(3) 146.5 3_756
C7 H7B F1 0.97 2.52 3.412(3) 152.2 4_556
C8 H8 O3 0.93 2.46 3.173(2) 133.4 2_646

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
F1 C4 C3 C2 179.02(18) . . . . ?
C10 C11 C12 N1 -0.3(3) . . . . ?
C10 C9 C8 N1 0.4(4) . . . . ?
C1 C2 C7 O1 1.0(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C6 C5 C4 0.3(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 B1 O2 -177.8(2) . . . . ?
C2 C1 B1 O1 1.6(2) . . . . ?
C11 C10 C13 O3 172.1(2) . . . . ?
C11 C10 C13 N2 -7.6(3) . . . . ?
C11 C10 C9 C8 0.2(3) . . . . ?
C13 C10 C11 C12 -179.14(19) . . . . ?
C13 C10 C9 C8 179.1(2) . . . . ?
C6 C1 C2 C7 179.14(18) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C6 C1 B1 O2 1.3(4) . . . . ?
C6 C1 B1 O1 -179.3(2) . . . . ?
C6 C5 C4 F1 -179.42(19) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C9 C10 C13 O3 -6.8(3) . . . . ?
C9 C10 C13 N2 173.5(2) . . . . ?
C12 N1 C8 C9 -1.0(3) . . . . ?
C7 O1 B1 O2 178.5(2) . . . . ?
C7 O1 B1 C1 -1.0(2) . . . . ?
C7 C2 C3 C4 -179.1(2) . . . . ?
C3 C2 C7 O1 -179.33(19) . . . . ?
C8 N1 C12 C11 0.9(3) . . . . ?
B1 O1 C7 C2 0.0(2) . . . . ?
B1 C1 C2 C7 -1.5(2) . . . . ?
B1 C1 C2 C3 178.80(18) . . . . ?
B1 C1 C6 C5 -178.9(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_mcg16173a
_database_code_depnum_ccdc_archive 'CCDC 1531824'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;
_audit_creation_date             2017-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            2(AN2690)(bpeta)
_chemical_name_systematic        
'5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole, 1,2-bis(4-pyridyl)ethane'
_chemical_formula_moiety         '2(C7 H6 B F O2), C12 H12 N2'
_chemical_formula_sum            'C26 H24 B2 F2 N2 O4'
_chemical_formula_weight         488.09
_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                   15.0294(15)
_cell_length_b                   5.9476(6)
_cell_length_c                   14.5384(15)
_cell_angle_alpha                90
_cell_angle_beta                 110.690(5)
_cell_angle_gamma                90
_cell_volume                     1215.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      1.00
_cell_measurement_theta_min      25.35
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             508
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
"Slow evaporation of a methanol solution containing 1 equivalent of 4,4'-bpeta and 2 equivalents of AN2690"
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6955
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.367
_diffrn_reflns_theta_max         25.367
_diffrn_reflns_theta_min         2.829
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1760
_reflns_number_total             2208
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²+0.2480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1443
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C9(H9), C8(H8), C11(H11), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.28717(9) 0.6157(2) 0.50189(8) 0.0632(4) Uani 1 1 d . . . . .
O2 O 0.21813(10) 0.9504(2) 0.53922(10) 0.0687(4) Uani 1 1 d . . . . .
H2 H 0.1974 0.9578 0.4790 0.103 Uiso 1 1 calc GR . . . .
F1 F 0.47226(10) 0.2846(2) 0.90998(9) 0.0948(5) Uani 1 1 d . . . . .
N1 N 0.14821(11) 1.0131(3) 0.33988(12) 0.0653(4) Uani 1 1 d . . . . .
C2 C 0.36587(11) 0.4736(3) 0.66075(12) 0.0505(4) Uani 1 1 d . . . . .
C1 C 0.32451(11) 0.6751(3) 0.67321(12) 0.0490(4) Uani 1 1 d . . . . .
C6 C 0.33496(12) 0.7441(3) 0.76794(13) 0.0573(5) Uani 1 1 d . . . . .
H6 H 0.3083 0.8791 0.7776 0.069 Uiso 1 1 calc R . . . .
C7 C 0.34664(14) 0.4331(3) 0.55350(13) 0.0625(5) Uani 1 1 d . . . . .
H7A H 0.4057 0.4310 0.5405 0.075 Uiso 1 1 calc R . . . .
H7B H 0.3145 0.2904 0.5331 0.075 Uiso 1 1 calc R . . . .
C3 C 0.41652(12) 0.3394(3) 0.73965(13) 0.0585(5) Uani 1 1 d . . . . .
H3 H 0.4442 0.2049 0.7310 0.070 Uiso 1 1 calc R . . . .
C5 C 0.38497(13) 0.6122(3) 0.84777(13) 0.0637(5) Uani 1 1 d . . . . .
H5 H 0.3921 0.6562 0.9114 0.076 Uiso 1 1 calc R . . . .
C4 C 0.42389(13) 0.4143(3) 0.83088(13) 0.0619(5) Uani 1 1 d . . . . .
C10 C 0.08617(12) 1.0031(4) 0.13451(15) 0.0674(6) Uani 1 1 d . . . . .
C9 C 0.13652(13) 1.1840(4) 0.18788(15) 0.0695(6) Uani 1 1 d . . . . .
H9 H 0.1508 1.3061 0.1556 0.083 Uiso 1 1 calc R . . . .
B1 B 0.27234(14) 0.7647(3) 0.56776(15) 0.0538(5) Uani 1 1 d . . . . .
C8 C 0.16519(14) 1.1821(3) 0.28839(15) 0.0690(5) Uani 1 1 d . . . . .
H8 H 0.1984 1.3061 0.3226 0.083 Uiso 1 1 calc R . . . .
C11 C 0.06883(14) 0.8267(4) 0.18793(16) 0.0734(6) Uani 1 1 d . . . . .
H11 H 0.0355 0.7008 0.1557 0.088 Uiso 1 1 calc R . . . .
C12 C 0.10103(14) 0.8381(4) 0.28876(15) 0.0693(5) Uani 1 1 d . . . . .
H12 H 0.0892 0.7168 0.3231 0.083 Uiso 1 1 calc R . . . .
C13 C 0.05168(14) 0.9952(6) 0.02429(16) 0.0927(8) Uani 1 1 d . . . . .
H13A H 0.0796 1.1201 0.0011 0.111 Uiso 1 1 calc R . . . .
H13B H 0.0746 0.8576 0.0045 0.111 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
O1 C7 1.438(2) . ?
O1 B1 1.380(2) . ?
O2 H2 0.8200 . ?
O2 B1 1.348(2) . ?
F1 C4 1.362(2) . ?
N1 C8 1.331(2) . ?
N1 C12 1.329(3) . ?
C2 C1 1.391(2) . ?
C2 C7 1.501(2) . ?
C2 C3 1.384(2) . ?
C1 C6 1.392(2) . ?
C1 B1 1.549(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.366(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.374(3) . ?
C10 C9 1.385(3) . ?
C10 C11 1.384(3) . ?
C10 C13 1.501(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.370(3) . ?
C8 H8 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C13 1.463(4) 3_575 ?
C13 H13A 0.9700 . ?
C13 H13B 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
B1 O1 C7 110.26(14) . . ?
B1 O2 H2 109.5 . . ?
C12 N1 C8 116.59(17) . . ?
C1 C2 C7 110.04(15) . . ?
C3 C2 C1 121.96(16) . . ?
C3 C2 C7 128.00(16) . . ?
C2 C1 C6 118.91(16) . . ?
C2 C1 B1 105.13(14) . . ?
C6 C1 B1 135.92(16) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.08(17) . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C2 106.06(14) . . ?
O1 C7 H7A 110.5 . . ?
O1 C7 H7B 110.5 . . ?
C2 C7 H7A 110.5 . . ?
C2 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C2 C3 H3 121.7 . . ?
C4 C3 C2 116.65(17) . . ?
C4 C3 H3 121.7 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.39(17) . . ?
C4 C5 H5 120.8 . . ?
F1 C4 C3 118.09(18) . . ?
F1 C4 C5 117.91(17) . . ?
C3 C4 C5 124.00(17) . . ?
C9 C10 C13 122.5(2) . . ?
C11 C10 C9 116.66(19) . . ?
C11 C10 C13 120.9(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.69(19) . . ?
C8 C9 H9 120.2 . . ?
O1 B1 C1 108.44(16) . . ?
O2 B1 O1 122.76(17) . . ?
O2 B1 C1 128.78(17) . . ?
N1 C8 C9 123.7(2) . . ?
N1 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
N1 C12 C11 123.57(19) . . ?
N1 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C10 C13 H13A 108.5 . . ?
C10 C13 H13B 108.5 . . ?
C13 C13 C10 114.9(2) 3_575 . ?
C13 C13 H13A 108.5 3_575 . ?
C13 C13 H13B 108.5 3_575 . ?
H13A C13 H13B 107.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.82 1.92 2.737(2) 173.2 .
C7 H7B O2 0.97 2.51 3.425(2) 157.9 1_545

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
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 B1 O1 -0.84(18) . . . . ?
C2 C1 B1 O2 177.20(18) . . . . ?
C2 C3 C4 F1 179.17(15) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C1 C2 C7 O1 -2.95(18) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C6 C5 C4 0.3(3) . . . . ?
C6 C1 B1 O1 -178.59(17) . . . . ?
C6 C1 B1 O2 -0.6(3) . . . . ?
C6 C5 C4 F1 -179.39(17) . . . . ?
C6 C5 C4 C3 0.2(3) . . . . ?
C7 O1 B1 O2 -179.21(16) . . . . ?
C7 O1 B1 C1 -1.03(19) . . . . ?
C7 C2 C1 C6 -179.49(15) . . . . ?
C7 C2 C1 B1 2.29(18) . . . . ?
C7 C2 C3 C4 179.99(16) . . . . ?
C3 C2 C1 C6 0.4(2) . . . . ?
C3 C2 C1 B1 -177.81(15) . . . . ?
C3 C2 C7 O1 177.16(16) . . . . ?
C10 C9 C8 N1 0.6(3) . . . . ?
C10 C11 C12 N1 0.7(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C13 C13 -112.3(3) . . . 3_575 ?
B1 O1 C7 C2 2.37(19) . . . . ?
B1 C1 C6 C5 176.89(18) . . . . ?
C8 N1 C12 C11 -1.0(3) . . . . ?
C11 C10 C9 C8 -0.8(3) . . . . ?
C11 C10 C13 C13 67.8(4) . . . 3_575 ?
C12 N1 C8 C9 0.3(3) . . . . ?
C13 C10 C9 C8 179.30(18) . . . . ?
C13 C10 C11 C12 -179.90(19) . . . . ?

_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_mcg16168a
_database_code_depnum_ccdc_archive 'CCDC 1531823'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;
_audit_creation_date             2017-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            2(AN2690)(bpe)
_chemical_name_systematic        
'5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole, 1,2-bis(4-pyridyl)ethylene'
_chemical_formula_moiety         '2(C7 H6 B F O2), C12 H10 N2'
_chemical_formula_sum            'C26 H22 B2 F2 N2 O4'
_chemical_formula_weight         486.07
_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                   14.8742(15)
_cell_length_b                   5.9305(6)
_cell_length_c                   14.3285(14)
_cell_angle_alpha                90
_cell_angle_beta                 109.171(5)
_cell_angle_gamma                90
_cell_volume                     1193.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3888
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_correction_T_min  0.9353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
"Slow evaporation of a methanol solution containing 1 equivalent of 4,4'-bpe and 2 equivalents of AN2690"
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6833
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.279
_diffrn_reflns_theta_max         25.279
_diffrn_reflns_theta_min         2.900
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1756
_reflns_number_total             2162
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      0.999
_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)+(0.0790P)²+0.1010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1186
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C9(H9), C3(H3), C8(H8), C11(H11), C5(H5), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.28059(7) 0.59538(16) 0.50248(7) 0.0661(3) Uani 1 1 d . . . . .
O2 O 0.21200(8) 0.93089(17) 0.54262(7) 0.0718(3) Uani 1 1 d . . . . .
H2 H 0.1950 0.9445 0.4824 0.108 Uiso 1 1 calc GR . . . .
F1 F 0.47640(8) 0.2775(2) 0.91168(7) 0.0971(4) Uani 1 1 d . . . . .
N1 N 0.15051(8) 1.0151(2) 0.34356(9) 0.0655(3) Uani 1 1 d . . . . .
C2 C 0.36261(9) 0.4569(2) 0.66170(10) 0.0530(3) Uani 1 1 d . . . . .
C1 C 0.32009(9) 0.6574(2) 0.67540(9) 0.0517(3) Uani 1 1 d . . . . .
C10 C 0.07714(9) 1.0384(2) 0.13628(11) 0.0566(4) Uani 1 1 d . . . . .
C13 C 0.03532(9) 1.0612(2) 0.02942(11) 0.0614(4) Uani 1 1 d . . . . .
H13 H 0.0606 1.1724 -0.0004 0.074 Uiso 1 1 calc R . . . .
C6 C 0.33239(10) 0.7287(3) 0.77139(10) 0.0604(4) Uani 1 1 d . . . . .
H6 H 0.3048 0.8628 0.7819 0.073 Uiso 1 1 calc R . . . .
C7 C 0.34183(12) 0.4144(2) 0.55332(11) 0.0661(4) Uani 1 1 d . . . . .
H7A H 0.4003 0.4138 0.5373 0.079 Uiso 1 1 calc R . . . .
H7B H 0.3104 0.2701 0.5346 0.079 Uiso 1 1 calc R . . . .
C9 C 0.13316(9) 1.2098(2) 0.19268(10) 0.0610(4) Uani 1 1 d . . . . .
H9 H 0.1479 1.3359 0.1619 0.073 Uiso 1 1 calc R . . . .
C3 C 0.41590(10) 0.3263(3) 0.74035(10) 0.0613(4) Uani 1 1 d . . . . .
H3 H 0.4442 0.1923 0.7308 0.074 Uiso 1 1 calc R . . . .
C8 C 0.16670(10) 1.1923(3) 0.29389(11) 0.0639(4) Uani 1 1 d . . . . .
H8 H 0.2028 1.3107 0.3299 0.077 Uiso 1 1 calc R . . . .
C4 C 0.42495(10) 0.4038(3) 0.83272(11) 0.0650(4) Uani 1 1 d . . . . .
C11 C 0.06273(10) 0.8502(3) 0.18845(12) 0.0649(4) Uani 1 1 d . . . . .
H11 H 0.0277 0.7280 0.1547 0.078 Uiso 1 1 calc R . . . .
C5 C 0.38538(10) 0.6012(3) 0.85090(11) 0.0669(4) Uani 1 1 d . . . . .
H5 H 0.3941 0.6477 0.9153 0.080 Uiso 1 1 calc R . . . .
C12 C 0.10027(10) 0.8465(3) 0.28914(12) 0.0672(4) Uani 1 1 d . . . . .
H12 H 0.0902 0.7185 0.3219 0.081 Uiso 1 1 calc R . . . .
B1 B 0.26581(12) 0.7447(3) 0.56977(12) 0.0561(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
O1 C7 1.4409(18) . ?
O1 B1 1.3790(18) . ?
O2 H2 0.8200 . ?
O2 B1 1.3439(19) . ?
F1 C4 1.3632(17) . ?
N1 C8 1.3344(19) . ?
N1 C12 1.336(2) . ?
C2 C1 1.3909(18) . ?
C2 C7 1.5017(19) . ?
C2 C3 1.3825(19) . ?
C1 C6 1.3926(18) . ?
C1 B1 1.552(2) . ?
C10 C13 1.457(2) . ?
C10 C9 1.3924(19) . ?
C10 C11 1.398(2) . ?
C13 C13 1.327(3) 3_575 ?
C13 H13 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.379(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C8 1.374(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(2) . ?
C8 H8 0.9300 . ?
C4 C5 1.373(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(2) . ?
C5 H5 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C7 110.15(11) . . ?
B1 O2 H2 109.5 . . ?
C8 N1 C12 116.27(13) . . ?
C1 C2 C7 109.91(12) . . ?
C3 C2 C1 121.97(12) . . ?
C3 C2 C7 128.12(13) . . ?
C2 C1 C6 118.74(12) . . ?
C2 C1 B1 105.24(11) . . ?
C6 C1 B1 136.01(13) . . ?
C9 C10 C13 120.63(13) . . ?
C9 C10 C11 116.11(14) . . ?
C11 C10 C13 123.24(13) . . ?
C10 C13 H13 116.8 . . ?
C13 C13 C10 126.35(17) 3_575 . ?
C13 C13 H13 116.8 3_575 . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.23(14) . . ?
C5 C6 H6 119.9 . . ?
O1 C7 C2 106.22(11) . . ?
O1 C7 H7A 110.5 . . ?
O1 C7 H7B 110.5 . . ?
C2 C7 H7A 110.5 . . ?
C2 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C10 C9 H9 120.1 . . ?
C8 C9 C10 119.86(13) . . ?
C8 C9 H9 120.1 . . ?
C2 C3 H3 121.7 . . ?
C4 C3 C2 116.68(14) . . ?
C4 C3 H3 121.7 . . ?
N1 C8 C9 123.78(14) . . ?
N1 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
F1 C4 C3 117.97(15) . . ?
F1 C4 C5 118.03(13) . . ?
C3 C4 C5 124.00(14) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.76(14) . . ?
C12 C11 H11 120.1 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.38(14) . . ?
C4 C5 H5 120.8 . . ?
N1 C12 C11 124.13(14) . . ?
N1 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
O1 B1 C1 108.43(12) . . ?
O2 B1 O1 122.81(13) . . ?
O2 B1 C1 128.76(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.82 1.92 2.7401(15) 172.6 .
C7 H7B O2 0.97 2.51 3.4324(19) 158.4 1_545
C9 H9 O2 0.93 2.61 3.4920(17) 158.4 4_585
C5 H5 F1 0.93 2.63 3.4240(19) 143.7 3_667

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
F1 C4 C5 C6 -179.32(13) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C1 B1 O1 -0.80(15) . . . . ?
C2 C1 B1 O2 178.90(14) . . . . ?
C2 C3 C4 F1 179.42(12) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C1 C2 C7 O1 -2.69(15) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C1 C6 C5 C4 -0.2(2) . . . . ?
C10 C9 C8 N1 1.4(2) . . . . ?
C10 C11 C12 N1 0.7(2) . . . . ?
C13 C10 C9 C8 175.60(12) . . . . ?
C13 C10 C11 C12 -176.56(13) . . . . ?
C6 C1 B1 O1 -179.43(14) . . . . ?
C6 C1 B1 O2 0.3(3) . . . . ?
C7 O1 B1 O2 179.38(14) . . . . ?
C7 O1 B1 C1 -0.89(15) . . . . ?
C7 C2 C1 C6 -178.98(12) . . . . ?
C7 C2 C1 B1 2.10(14) . . . . ?
C7 C2 C3 C4 179.31(13) . . . . ?
C9 C10 C13 C13 -163.50(18) . . . 3_575 ?
C9 C10 C11 C12 2.1(2) . . . . ?
C3 C2 C1 C6 0.46(19) . . . . ?
C3 C2 C1 B1 -178.45(12) . . . . ?
C3 C2 C7 O1 177.92(13) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C8 N1 C12 C11 -2.6(2) . . . . ?
C11 C10 C13 C13 15.2(3) . . . 3_575 ?
C11 C10 C9 C8 -3.1(2) . . . . ?
C12 N1 C8 C9 1.5(2) . . . . ?
B1 O1 C7 C2 2.13(15) . . . . ?
B1 C1 C6 C5 178.14(14) . . . . ?

_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_mcg16171a
_database_code_depnum_ccdc_archive 'CCDC 1531822'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;
_audit_creation_date             2017-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            2(AN2690)(bpy)
_chemical_name_systematic        
"5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole, 4,4'-bipyridine"
_chemical_formula_moiety         '2(C7 H6 B F O2), C10 H8 N2'
_chemical_formula_sum            'C24 H20 B2 F2 N2 O4'
_chemical_formula_weight         460.04
_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                   14.5378(15)
_cell_length_b                   6.0517(6)
_cell_length_c                   14.4276(14)
_cell_angle_alpha                90
_cell_angle_beta                 118.366(5)
_cell_angle_gamma                90
_cell_volume                     1116.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3888
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.8831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
"Slow evaporation of a methanol solution containing 1 equivalent of 4,4'-bpy and 2 equivalents of AN2690"
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6425
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.375
_diffrn_reflns_theta_max         25.375
_diffrn_reflns_theta_min         3.185
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1515
_reflns_number_total             2036
_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       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.088
_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)+(0.0530P)²+0.1450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1153
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C9(H9), C8(H8), C11(H11), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.76481(9) 0.40033(19) 0.46440(9) 0.0748(4) Uani 1 1 d . . . . .
O2 O 0.69401(10) 0.0647(2) 0.49076(10) 0.0832(4) Uani 1 1 d . . . . .
H2 H 0.6761 0.0529 0.4278 0.125 Uiso 1 1 calc GR . . . .
F1 F 0.97316(9) 0.7150(2) 0.90665(8) 0.1093(5) Uani 1 1 d . . . . .
N1 N 0.62617(11) -0.0025(3) 0.28017(12) 0.0784(4) Uani 1 1 d . . . . .
C1 C 0.80724(11) 0.3378(2) 0.64304(12) 0.0585(4) Uani 1 1 d . . . . .
C2 C 0.85135(11) 0.5379(2) 0.63730(12) 0.0591(4) Uani 1 1 d . . . . .
C7 C 0.82868(15) 0.5812(3) 0.52594(13) 0.0747(5) Uani 1 1 d . . . . .
H7A H 0.7919 0.7202 0.5010 0.090 Uiso 1 1 calc R . . . .
H7B H 0.8931 0.5876 0.5214 0.090 Uiso 1 1 calc R . . . .
C10 C 0.52655(11) -0.0006(3) 0.05841(14) 0.0664(4) Uani 1 1 d . . . . .
C6 C 0.82178(13) 0.2665(3) 0.74075(13) 0.0691(4) Uani 1 1 d . . . . .
H6 H 0.7934 0.1325 0.7462 0.083 Uiso 1 1 calc R . . . .
C3 C 0.90786(12) 0.6677(3) 0.72547(13) 0.0680(4) Uani 1 1 d . . . . .
H3 H 0.9370 0.8017 0.7213 0.082 Uiso 1 1 calc R . . . .
C5 C 0.87776(13) 0.3925(3) 0.82925(14) 0.0758(5) Uani 1 1 d . . . . .
H5 H 0.8878 0.3455 0.8948 0.091 Uiso 1 1 calc R . . . .
C9 C 0.58887(14) -0.1753(3) 0.11753(15) 0.0785(5) Uani 1 1 d . . . . .
H9 H 0.5990 -0.2965 0.0838 0.094 Uiso 1 1 calc R . . . .
C4 C 0.91857(13) 0.5895(3) 0.81860(13) 0.0734(5) Uani 1 1 d . . . . .
C8 C 0.63532(14) -0.1698(3) 0.22506(15) 0.0821(5) Uani 1 1 d . . . . .
H8 H 0.6758 -0.2903 0.2621 0.099 Uiso 1 1 calc R . . . .
C11 C 0.51838(14) 0.1743(3) 0.11604(15) 0.0815(5) Uani 1 1 d . . . . .
H11 H 0.4783 0.2972 0.0814 0.098 Uiso 1 1 calc R . . . .
C12 C 0.56916(15) 0.1669(3) 0.22396(16) 0.0841(5) Uani 1 1 d . . . . .
H12 H 0.5632 0.2887 0.2601 0.101 Uiso 1 1 calc R . . . .
B1 B 0.75002(14) 0.2512(3) 0.52844(15) 0.0644(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.437(2) . ?
O1 B1 1.380(2) . ?
O2 H2 0.8200 . ?
O2 B1 1.346(2) . ?
F1 C4 1.3647(19) . ?
N1 C8 1.332(2) . ?
N1 C12 1.326(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.391(2) . ?
C1 B1 1.547(2) . ?
C2 C7 1.502(2) . ?
C2 C3 1.385(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 C10 1.483(4) 3_655 ?
C10 C9 1.390(2) . ?
C10 C11 1.386(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.374(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.367(2) . ?
C8 H8 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.371(3) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C7 110.18(13) . . ?
B1 O2 H2 109.5 . . ?
C12 N1 C8 115.67(17) . . ?
C2 C1 C6 118.56(15) . . ?
C2 C1 B1 105.09(13) . . ?
C6 C1 B1 136.34(15) . . ?
C1 C2 C7 110.03(14) . . ?
C3 C2 C1 121.89(15) . . ?
C3 C2 C7 128.08(14) . . ?
O1 C7 C2 106.09(13) . . ?
O1 C7 H7A 110.5 . . ?
O1 C7 H7B 110.5 . . ?
C2 C7 H7A 110.5 . . ?
C2 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C9 C10 C10 122.47(19) . 3_655 ?
C11 C10 C10 122.1(2) . 3_655 ?
C11 C10 C9 115.44(17) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.49(16) . . ?
C5 C6 H6 119.8 . . ?
C2 C3 H3 121.7 . . ?
C4 C3 C2 116.68(16) . . ?
C4 C3 H3 121.7 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.36(16) . . ?
C4 C5 H5 120.8 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.30(16) . . ?
C8 C9 H9 119.9 . . ?
F1 C4 C5 118.07(16) . . ?
C3 C4 F1 117.92(17) . . ?
C3 C4 C5 124.01(16) . . ?
N1 C8 C9 124.09(18) . . ?
N1 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.20(18) . . ?
C12 C11 H11 119.9 . . ?
N1 C12 C11 124.26(17) . . ?
N1 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
O1 B1 C1 108.56(14) . . ?
O2 B1 O1 122.33(16) . . ?
O2 B1 C1 129.11(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.82 1.93 2.7427(19) 173.9 .
C7 H7A O2 0.97 2.49 3.422(2) 161.4 1_565
C5 H5 F1 0.93 2.63 3.434(2) 144.8 3_767

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
C1 C2 C7 O1 2.33(18) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C2 C1 B1 O1 0.74(17) . . . . ?
C2 C1 B1 O2 -179.38(16) . . . . ?
C2 C3 C4 F1 -179.47(14) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C7 O1 B1 O2 -179.16(15) . . . . ?
C7 O1 B1 C1 0.72(18) . . . . ?
C7 C2 C3 C4 -179.05(15) . . . . ?
C10 C10 C9 C8 -179.32(19) 3_655 . . . ?
C10 C10 C11 C12 -179.69(18) 3_655 . . . ?
C10 C9 C8 N1 -0.7(3) . . . . ?
C10 C11 C12 N1 -1.4(3) . . . . ?
C6 C1 C2 C7 178.66(14) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C6 C1 B1 O1 -179.91(16) . . . . ?
C6 C1 B1 O2 0.0(3) . . . . ?
C6 C5 C4 F1 179.31(15) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C3 C2 C7 O1 -178.32(14) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C8 N1 C12 C11 2.2(3) . . . . ?
C11 C10 C9 C8 1.5(2) . . . . ?
C12 N1 C8 C9 -1.1(3) . . . . ?
B1 O1 C7 C2 -1.81(18) . . . . ?
B1 C1 C2 C7 -1.85(16) . . . . ?
B1 C1 C2 C3 178.75(14) . . . . ?
B1 C1 C6 C5 -178.70(16) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
