# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 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_phen-py
_database_code_depnum_ccdc_archive 'CCDC 1880203'
loop_
_audit_author_name
_audit_author_address
'Kenta Goto'
;Kyushu University
Japan
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;
_audit_creation_date             2018-11-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 B F2 N2 O'
_chemical_formula_sum            'C20 H13 B F2 N2 O'
_chemical_formula_weight         346.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H B F O'
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                   7.2247(7)
_cell_length_b                   8.2901(6)
_cell_length_c                   12.9787(14)
_cell_angle_alpha                94.973(7)
_cell_angle_beta                 93.331(8)
_cell_angle_gamma                98.458(7)
_cell_volume                     764.01(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2006
_cell_measurement_temperature    123
_cell_measurement_theta_max      28.0780
_cell_measurement_theta_min      2.4540
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7323
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.495
_diffrn_ambient_temperature      123
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00 -56.00   0.50    1.50    --    4.70  45.00 150.00   54
  2  ω    -46.00  39.00   0.50    1.50    --    4.70  45.00 150.00  170
  3  ω     42.00  94.00   0.50    1.50    --    4.70  45.00 150.00  104
  4  ω    -78.00  94.00   0.50    1.50    --    4.70  45.00  60.00  344
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0009968000
_diffrn_orient_matrix_UB_12      0.0040182000
_diffrn_orient_matrix_UB_13      0.0547749000
_diffrn_orient_matrix_UB_21      -0.0022564000
_diffrn_orient_matrix_UB_22      0.0854580000
_diffrn_orient_matrix_UB_23      0.0020052000
_diffrn_orient_matrix_UB_31      -0.0994836000
_diffrn_orient_matrix_UB_32      -0.0152750000
_diffrn_orient_matrix_UB_33      -0.0045504000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2131
_reflns_number_total             2772
_reflns_odcompleteness_completeness 99.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.227
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.024
_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)+(0.0722P)²+0.0786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C4(H4), C6(H6), C9(H9), C17(H17), C19(H19), C8(H8), C7(H7), C3(H3),
 C14(H14), C12(H12), C18(H18), C13(H13)
;
_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
F1 F 0.32738(14) 0.27163(11) 0.85849(8) 0.0389(3) Uani 1 1 d . . . . .
F2 F 0.63881(14) 0.27815(11) 0.84270(8) 0.0370(3) Uani 1 1 d . . . . .
O1 O 0.44058(18) 0.25799(13) 0.69458(9) 0.0326(3) Uani 1 1 d . . . . .
N2 N 0.49924(17) 0.51559(15) 0.80567(10) 0.0203(3) Uani 1 1 d . . . . .
N1 N 0.34814(18) 0.48966(15) 0.63506(10) 0.0217(3) Uani 1 1 d . . . . .
C15 C 0.3584(2) 0.33538(18) 0.62400(12) 0.0204(4) Uani 1 1 d . . . . .
C11 C 0.1268(2) 0.16272(18) 0.35322(12) 0.0215(4) Uani 1 1 d . . . . .
C2 C 0.1984(2) 0.28237(18) 0.43760(12) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.0424(2) 0.38127(19) 0.24964(12) 0.0210(4) Uani 1 1 d . . . . .
C1 C 0.2803(2) 0.22763(18) 0.52902(12) 0.0206(4) Uani 1 1 d . . . . .
C10 C 0.0462(2) 0.21305(19) 0.25828(12) 0.0211(4) Uani 1 1 d . . . . .
C16 C 0.4279(2) 0.58333(19) 0.72400(12) 0.0208(4) Uani 1 1 d . . . . .
C20 C 0.5759(2) 0.61069(19) 0.89201(12) 0.0233(4) Uani 1 1 d . . . . .
H20 H 0.626045 0.560712 0.948295 0.028 Uiso 1 1 calc R . . . .
C4 C 0.1138(2) 0.49644(19) 0.33618(12) 0.0229(4) Uani 1 1 d . . . . .
H4 H 0.109563 0.609461 0.330996 0.028 Uiso 1 1 calc R . . . .
C6 C -0.0293(2) 0.4335(2) 0.15729(12) 0.0237(4) Uani 1 1 d . . . . .
H6 H -0.032161 0.546830 0.152673 0.028 Uiso 1 1 calc R . . . .
C9 C -0.0255(2) 0.10251(19) 0.17125(12) 0.0245(4) Uani 1 1 d . . . . .
H9 H -0.026750 -0.011588 0.174960 0.029 Uiso 1 1 calc R . . . .
C17 C 0.4355(2) 0.75300(19) 0.72892(13) 0.0239(4) Uani 1 1 d . . . . .
H17 H 0.387973 0.802025 0.671476 0.029 Uiso 1 1 calc R . . . .
C19 C 0.5828(2) 0.77651(19) 0.90014(13) 0.0247(4) Uani 1 1 d . . . . .
H19 H 0.635353 0.841547 0.961665 0.030 Uiso 1 1 calc R . . . .
C8 C -0.0932(2) 0.1561(2) 0.08172(13) 0.0268(4) Uani 1 1 d . . . . .
H8 H -0.139508 0.078867 0.024275 0.032 Uiso 1 1 calc R . . . .
C7 C -0.0952(2) 0.3230(2) 0.07377(13) 0.0264(4) Uani 1 1 d . . . . .
H7 H -0.141620 0.359354 0.011251 0.032 Uiso 1 1 calc R . . . .
C3 C 0.1870(2) 0.45042(19) 0.42490(12) 0.0224(4) Uani 1 1 d . . . . .
H3 H 0.232111 0.531604 0.480413 0.027 Uiso 1 1 calc R . . . .
C14 C 0.2891(2) 0.06347(19) 0.53296(13) 0.0283(4) Uani 1 1 d . . . . .
H14 H 0.343733 0.027987 0.593727 0.034 Uiso 1 1 calc R . . . .
C12 C 0.1402(2) -0.0024(2) 0.36274(13) 0.0289(4) Uani 1 1 d . . . . .
H12 H 0.092383 -0.081929 0.306799 0.035 Uiso 1 1 calc R . . . .
C18 C 0.5117(2) 0.8487(2) 0.81694(13) 0.0273(4) Uani 1 1 d . . . . .
H18 H 0.515760 0.964113 0.820994 0.033 Uiso 1 1 calc R . . . .
C13 C 0.2199(3) -0.0519(2) 0.45000(14) 0.0337(4) Uani 1 1 d . . . . .
H13 H 0.228194 -0.164513 0.454258 0.040 Uiso 1 1 calc R . . . .
B1 B 0.4773(3) 0.3244(2) 0.80190(14) 0.0259(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 1.383(2) . ?
F2 B1 1.372(2) . ?
O1 C15 1.3244(18) . ?
O1 B1 1.447(2) . ?
N2 C16 1.3525(19) . ?
N2 C20 1.3528(19) . ?
N2 B1 1.566(2) . ?
N1 C15 1.288(2) . ?
N1 C16 1.3796(19) . ?
C15 C1 1.489(2) . ?
C11 C2 1.430(2) . ?
C11 C10 1.452(2) . ?
C11 C12 1.402(2) . ?
C2 C1 1.433(2) . ?
C2 C3 1.431(2) . ?
C5 C10 1.413(2) . ?
C5 C4 1.429(2) . ?
C5 C6 1.406(2) . ?
C1 C14 1.377(2) . ?
C10 C9 1.413(2) . ?
C16 C17 1.395(2) . ?
C20 C19 1.363(2) . ?
C4 C3 1.347(2) . ?
C6 C7 1.371(2) . ?
C9 C8 1.369(2) . ?
C17 C18 1.371(2) . ?
C19 C18 1.388(2) . ?
C8 C7 1.398(2) . ?
C14 C13 1.394(2) . ?
C12 C13 1.363(2) . ?

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
C15 O1 B1 122.47(13) . . ?
C16 N2 C20 120.58(13) . . ?
C16 N2 B1 118.74(12) . . ?
C20 N2 B1 120.51(13) . . ?
C15 N1 C16 119.64(13) . . ?
O1 C15 C1 113.67(13) . . ?
N1 C15 O1 123.69(14) . . ?
N1 C15 C1 122.64(14) . . ?
C2 C11 C10 120.15(14) . . ?
C12 C11 C2 119.03(14) . . ?
C12 C11 C10 120.81(14) . . ?
C11 C2 C1 118.28(14) . . ?
C11 C2 C3 117.88(14) . . ?
C3 C2 C1 123.83(14) . . ?
C10 C5 C4 118.65(14) . . ?
C6 C5 C10 120.37(14) . . ?
C6 C5 C4 120.98(14) . . ?
C2 C1 C15 125.08(14) . . ?
C14 C1 C15 115.33(14) . . ?
C14 C1 C2 119.58(14) . . ?
C5 C10 C11 119.32(13) . . ?
C5 C10 C9 117.17(14) . . ?
C9 C10 C11 123.48(14) . . ?
N2 C16 N1 121.97(13) . . ?
N2 C16 C17 119.44(13) . . ?
N1 C16 C17 118.59(14) . . ?
N2 C20 C19 121.54(15) . . ?
C3 C4 C5 122.33(14) . . ?
C7 C6 C5 120.89(15) . . ?
C8 C9 C10 121.51(15) . . ?
C18 C17 C16 119.74(15) . . ?
C20 C19 C18 118.82(14) . . ?
C9 C8 C7 120.83(15) . . ?
C6 C7 C8 119.21(15) . . ?
C4 C3 C2 121.66(14) . . ?
C1 C14 C13 121.64(15) . . ?
C13 C12 C11 121.86(15) . . ?
C17 C18 C19 119.86(15) . . ?
C12 C13 C14 119.61(15) . . ?
F1 B1 O1 110.27(14) . . ?
F1 B1 N2 107.98(14) . . ?
F2 B1 F1 110.52(14) . . ?
F2 B1 O1 109.89(15) . . ?
F2 B1 N2 110.12(13) . . ?
O1 B1 N2 108.00(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.829

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

data_2-Np@py
_database_code_depnum_ccdc_archive 'CCDC 1881147'
loop_
_audit_author_name
_audit_author_address
'Kenta Goto'
;Kyushu University
Japan
;
_audit_update_record             
;
2018-11-26 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H11 B F2 N2 O'
_chemical_formula_moiety         'C16 H11 B F2 N2 O'
_chemical_formula_weight         296.08
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.0633(4)
_cell_length_b                   8.1684(4)
_cell_length_c                   11.4242(6)
_cell_angle_alpha                85.790(6)
_cell_angle_beta                 83.433(6)
_cell_angle_gamma                88.598(6)
_cell_volume                     652.96(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6256
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      68.20
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304.00
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  0.953

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            7851
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         3.905
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2338
_reflns_number_gt                1824
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1853
_refine_ls_wR_factor_gt          0.1564
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2338
_refine_ls_number_parameters     243
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1239P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.42625(19) 0.31900(13) 0.35631(10) 0.0385(4) Uani 1 2 d . . .
F2 F 0.10676(18) 0.36323(14) 0.37903(10) 0.0376(4) Uani 1 2 d . . .
O1 O 0.2657(2) 0.35820(16) 0.18903(12) 0.0323(4) Uani 1 2 d . . .
N1 N 0.3087(3) 0.59116(19) 0.30801(14) 0.0274(5) Uani 1 2 d . . .
N2 N 0.2858(3) 0.6247(2) 0.10103(15) 0.0280(4) Uani 1 2 d . . .
C1 C 0.2095(3) 0.2365(3) -0.02157(18) 0.0267(5) Uani 1 2 d . . .
C2 C 0.2365(3) 0.4009(2) -0.01477(17) 0.0269(5) Uani 1 2 d . . .
C3 C 0.2362(3) 0.5092(3) -0.11856(19) 0.0295(5) Uani 1 2 d . . .
C4 C 0.2071(3) 0.4501(3) -0.22280(18) 0.0303(5) Uani 1 2 d . . .
C5 C 0.1749(3) 0.2806(3) -0.23213(18) 0.0276(5) Uani 1 2 d . . .
C6 C 0.1420(3) 0.2158(3) -0.33920(18) 0.0318(5) Uani 1 2 d . . .
C7 C 0.1149(3) 0.0521(3) -0.34454(19) 0.0345(6) Uani 1 2 d . . .
C8 C 0.1238(3) -0.0573(3) -0.2433(2) 0.0345(6) Uani 1 2 d . . .
C9 C 0.1547(3) 0.0010(3) -0.13818(19) 0.0317(5) Uani 1 2 d . . .
C10 C 0.1806(3) 0.1713(3) -0.12936(18) 0.0272(5) Uani 1 2 d . . .
C11 C 0.2636(3) 0.4686(2) 0.09771(18) 0.0266(5) Uani 1 2 d . . .
C12 C 0.3134(3) 0.6877(2) 0.20562(18) 0.0269(5) Uani 1 2 d . . .
C13 C 0.3366(3) 0.6568(3) 0.41039(19) 0.0316(5) Uani 1 2 d . . .
C14 C 0.3736(3) 0.8188(3) 0.4145(2) 0.0340(6) Uani 1 2 d . . .
C15 C 0.3789(3) 0.9208(3) 0.3107(2) 0.0334(6) Uani 1 2 d . . .
C16 C 0.3510(3) 0.8548(3) 0.2073(2) 0.0307(5) Uani 1 2 d . . .
B1 B 0.2734(4) 0.4009(3) 0.3093(2) 0.0300(6) Uani 1 2 d . . .
H1 H 0.205(3) 0.165(3) 0.049(2) 0.047(7) Uiso 1 2 d . . .
H2 H 0.264(3) 0.627(3) -0.1148(19) 0.035(6) Uiso 1 2 d . . .
H3 H 0.203(3) 0.525(3) -0.2952(19) 0.042(6) Uiso 1 2 d . . .
H4 H 0.131(3) 0.289(3) -0.4095(19) 0.037(6) Uiso 1 2 d . . .
H5 H 0.084(4) 0.007(3) -0.416(2) 0.049(7) Uiso 1 2 d . . .
H6 H 0.092(3) -0.174(3) -0.2507(19) 0.035(6) Uiso 1 2 d . . .
H7 H 0.160(4) -0.077(3) -0.070(2) 0.040(6) Uiso 1 2 d . . .
H8 H 0.327(3) 0.579(3) 0.478(2) 0.044(7) Uiso 1 2 d . . .
H9 H 0.398(3) 0.858(3) 0.4903(19) 0.038(6) Uiso 1 2 d . . .
H10 H 0.414(3) 1.034(3) 0.3100(18) 0.032(6) Uiso 1 2 d . . .
H11 H 0.353(4) 0.918(3) 0.135(2) 0.052(7) Uiso 1 2 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 B1 1.395(3) yes . .
F2 B1 1.372(3) yes . .
O1 C11 1.329(2) yes . .
O1 B1 1.450(3) yes . .
N1 C12 1.359(2) yes . .
N1 C13 1.358(3) yes . .
N1 B1 1.578(3) yes . .
N2 C11 1.292(3) yes . .
N2 C12 1.371(3) yes . .
C1 C2 1.370(3) yes . .
C1 C10 1.414(3) yes . .
C2 C3 1.427(3) yes . .
C2 C11 1.469(3) yes . .
C3 C4 1.356(3) yes . .
C4 C5 1.422(3) yes . .
C5 C6 1.413(3) yes . .
C5 C10 1.426(3) yes . .
C6 C7 1.362(3) yes . .
C7 C8 1.415(3) yes . .
C8 C9 1.366(3) yes . .
C9 C10 1.420(3) yes . .
C12 C16 1.399(3) yes . .
C13 C14 1.360(3) yes . .
C14 C15 1.397(3) yes . .
C15 C16 1.370(3) yes . .
C1 H1 0.96(2) no . .
C3 H2 0.99(2) no . .
C4 H3 1.00(2) no . .
C6 H4 0.98(2) no . .
C7 H5 0.97(3) no . .
C8 H6 0.99(2) no . .
C9 H7 0.97(2) no . .
C13 H8 0.96(2) no . .
C14 H9 0.98(2) no . .
C15 H10 0.96(2) no . .
C16 H11 0.95(2) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C11 O1 B1 123.50(16) yes . . .
C12 N1 C13 120.43(17) yes . . .
C12 N1 B1 120.51(17) yes . . .
C13 N1 B1 119.05(16) yes . . .
C11 N2 C12 119.63(17) yes . . .
C2 C1 C10 121.46(18) yes . . .
C1 C2 C3 119.48(19) yes . . .
C1 C2 C11 121.35(17) yes . . .
C3 C2 C11 119.17(17) yes . . .
C2 C3 C4 120.22(19) yes . . .
C3 C4 C5 121.59(19) yes . . .
C4 C5 C6 122.86(19) yes . . .
C4 C5 C10 118.31(19) yes . . .
C6 C5 C10 118.81(19) yes . . .
C5 C6 C7 120.88(19) yes . . .
C6 C7 C8 120.6(2) yes . . .
C7 C8 C9 120.2(2) yes . . .
C8 C9 C10 120.60(19) yes . . .
C1 C10 C5 118.87(19) yes . . .
C1 C10 C9 122.16(18) yes . . .
C5 C10 C9 118.96(19) yes . . .
O1 C11 N2 125.47(19) yes . . .
O1 C11 C2 114.93(16) yes . . .
N2 C11 C2 119.59(18) yes . . .
N1 C12 N2 121.65(18) yes . . .
N1 C12 C16 118.8(2) yes . . .
N2 C12 C16 119.51(18) yes . . .
N1 C13 C14 121.93(19) yes . . .
C13 C14 C15 118.8(2) yes . . .
C14 C15 C16 119.3(2) yes . . .
C12 C16 C15 120.7(2) yes . . .
F1 B1 F2 109.89(17) yes . . .
F1 B1 O1 109.96(18) yes . . .
F1 B1 N1 107.62(19) yes . . .
F2 B1 O1 111.3(2) yes . . .
F2 B1 N1 109.27(17) yes . . .
O1 B1 N1 108.73(16) yes . . .
C2 C1 H1 119.0(15) no . . .
C10 C1 H1 119.4(15) no . . .
C2 C3 H2 119.5(13) no . . .
C4 C3 H2 120.2(12) no . . .
C3 C4 H3 120.7(14) no . . .
C5 C4 H3 117.7(14) no . . .
C5 C6 H4 120.0(14) no . . .
C7 C6 H4 119.0(14) no . . .
C6 C7 H5 121.6(14) no . . .
C8 C7 H5 117.8(14) no . . .
C7 C8 H6 116.9(13) no . . .
C9 C8 H6 122.6(12) no . . .
C8 C9 H7 118.4(15) no . . .
C10 C9 H7 121.0(15) no . . .
N1 C13 H8 113.7(15) no . . .
C14 C13 H8 124.3(15) no . . .
C13 C14 H9 118.3(13) no . . .
C15 C14 H9 122.9(13) no . . .
C14 C15 H10 120.5(13) no . . .
C16 C15 H10 120.0(13) no . . .
C12 C16 H11 116.6(16) no . . .
C15 C16 H11 122.7(16) no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C11 O1 B1 F1 -125.77(19) no . . . .
C11 O1 B1 F2 112.2(2) no . . . .
C11 O1 B1 N1 -8.2(3) no . . . .
B1 O1 C11 N2 6.9(3) no . . . .
B1 O1 C11 C2 -174.24(17) no . . . .
C12 N1 C13 C14 -1.3(3) no . . . .
C13 N1 C12 N2 179.98(18) no . . . .
C13 N1 C12 C16 1.2(3) no . . . .
C12 N1 B1 F1 123.60(19) no . . . .
C12 N1 B1 F2 -117.1(2) no . . . .
C12 N1 B1 O1 4.5(3) no . . . .
B1 N1 C12 N2 0.8(3) no . . . .
B1 N1 C12 C16 -178.01(17) no . . . .
C13 N1 B1 F1 -55.6(2) no . . . .
C13 N1 B1 F2 63.7(3) no . . . .
C13 N1 B1 O1 -174.68(17) no . . . .
B1 N1 C13 C14 177.92(18) no . . . .
C11 N2 C12 N1 -3.3(3) no . . . .
C11 N2 C12 C16 175.45(18) no . . . .
C12 N2 C11 O1 -0.3(3) no . . . .
C12 N2 C11 C2 -179.19(17) no . . . .
C2 C1 C10 C5 -1.6(3) no . . . .
C2 C1 C10 C9 179.26(18) no . . . .
C10 C1 C2 C3 -0.2(3) no . . . .
C10 C1 C2 C11 179.05(17) no . . . .
C1 C2 C3 C4 0.8(3) no . . . .
C1 C2 C11 O1 2.1(3) no . . . .
C1 C2 C11 N2 -178.97(18) no . . . .
C3 C2 C11 O1 -178.68(17) no . . . .
C3 C2 C11 N2 0.3(3) no . . . .
C11 C2 C3 C4 -178.49(17) no . . . .
C2 C3 C4 C5 0.5(3) no . . . .
C3 C4 C5 C6 179.25(19) no . . . .
C3 C4 C5 C10 -2.3(3) no . . . .
C4 C5 C6 C7 178.87(19) no . . . .
C4 C5 C10 C1 2.8(3) no . . . .
C4 C5 C10 C9 -178.04(17) no . . . .
C6 C5 C10 C1 -178.68(18) no . . . .
C6 C5 C10 C9 0.5(3) no . . . .
C10 C5 C6 C7 0.4(3) no . . . .
C5 C6 C7 C8 -1.5(3) no . . . .
C6 C7 C8 C9 1.7(3) no . . . .
C7 C8 C9 C10 -0.8(3) no . . . .
C8 C9 C10 C1 178.86(19) no . . . .
C8 C9 C10 C5 -0.3(3) no . . . .
N1 C12 C16 C15 -1.3(3) no . . . .
N2 C12 C16 C15 179.90(17) no . . . .
N1 C13 C14 C15 1.4(3) no . . . .
C13 C14 C15 C16 -1.5(3) no . . . .
C14 C15 C16 C12 1.4(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 C11 3.423(2) no . .
F1 C12 3.479(2) no . .
F1 C13 2.910(2) no . .
F2 C11 3.335(2) no . .
F2 C12 3.440(2) no . .
F2 C13 2.994(3) no . .
O1 C1 2.743(3) no . .
O1 C12 2.744(2) no . .
N1 C11 2.724(3) no . .
N1 C15 2.753(3) no . .
N2 C3 2.806(3) no . .
N2 B1 2.887(3) no . .
C1 C4 2.783(3) no . .
C2 C5 2.819(3) no . .
C3 C10 2.811(3) no . .
C5 C8 2.807(3) no . .
C6 C9 2.794(3) no . .
C7 C10 2.800(3) no . .
C11 C16 3.571(3) no . .
C12 C14 2.766(3) no . .
C13 C16 2.722(3) no . .
F1 C4 3.392(2) no . 2_665
F1 C13 3.326(3) no . 2_666
F1 C14 3.233(3) no . 2_666
F1 C15 3.362(2) no . 1_545
F2 C4 3.281(3) no . 2_565
F2 C6 3.387(2) no . 1_556
F2 C8 3.556(3) no . 2_555
N1 C4 3.462(3) no . 2_665
N1 C6 3.511(3) no . 2_565
N2 C2 3.411(3) no . 2_665
N2 C3 3.546(3) no . 2_665
N2 C5 3.516(3) no . 2_565
C1 C9 3.516(3) no . 2_555
C2 N2 3.411(3) no . 2_665
C2 C3 3.590(3) no . 2_565
C3 N2 3.546(3) no . 2_665
C3 C2 3.590(3) no . 2_565
C3 C11 3.512(3) no . 2_565
C3 C11 3.578(3) no . 2_665
C3 C12 3.599(3) no . 2_665
C4 F1 3.392(2) no . 2_665
C4 F2 3.281(3) no . 2_565
C4 N1 3.462(3) no . 2_665
C4 C11 3.533(3) no . 2_565
C4 C12 3.565(3) no . 2_665
C5 N2 3.516(3) no . 2_565
C5 C12 3.433(3) no . 2_565
C5 C15 3.573(3) no . 2_665
C5 C16 3.537(3) no . 2_665
C6 F2 3.387(2) no . 1_554
C6 N1 3.511(3) no . 2_565
C6 C12 3.497(3) no . 2_565
C6 C14 3.441(3) no . 2_665
C6 C15 3.581(3) no . 2_665
C7 C15 3.468(3) no . 2_565
C7 C16 3.569(3) no . 2_565
C8 F2 3.556(3) no . 2_555
C9 C1 3.516(3) no . 2_555
C10 C16 3.332(3) no . 2_665
C11 C3 3.512(3) no . 2_565
C11 C3 3.578(3) no . 2_665
C11 C4 3.533(3) no . 2_565
C12 C3 3.599(3) no . 2_665
C12 C4 3.565(3) no . 2_665
C12 C5 3.433(3) no . 2_565
C12 C6 3.497(3) no . 2_565
C13 F1 3.326(3) no . 2_666
C14 F1 3.233(3) no . 2_666
C14 C6 3.441(3) no . 2_665
C15 F1 3.362(2) no . 1_565
C15 C5 3.573(3) no . 2_665
C15 C6 3.581(3) no . 2_665
C15 C7 3.468(3) no . 2_565
C16 C5 3.537(3) no . 2_665
C16 C7 3.569(3) no . 2_565
C16 C10 3.332(3) no . 2_665
F1 H8 2.66(2) no . .
F2 H8 2.76(3) no . .
O1 H1 2.41(2) no . .
N1 H9 3.24(2) no . .
N1 H11 3.21(2) no . .
N2 H2 2.49(2) no . .
N2 H11 2.52(3) no . .
C1 H2 3.31(2) no . .
C1 H7 2.70(2) no . .
C2 H3 3.32(2) no . .
C3 H1 3.29(2) no . .
C4 H4 2.70(2) no . .
C5 H1 3.32(2) no . .
C5 H2 3.32(2) no . .
C5 H5 3.30(3) no . .
C5 H7 3.34(2) no . .
C6 H3 2.67(2) no . .
C6 H6 3.28(2) no . .
C7 H7 3.28(2) no . .
C8 H4 3.29(2) no . .
C9 H1 2.67(2) no . .
C9 H5 3.27(2) no . .
C10 H3 3.34(2) no . .
C10 H4 3.33(2) no . .
C10 H6 3.33(2) no . .
C11 H1 2.64(2) no . .
C11 H2 2.67(2) no . .
C12 H8 3.18(2) no . .
C12 H10 3.27(2) no . .
C13 H10 3.25(2) no . .
C14 H11 3.26(2) no . .
C15 H8 3.27(2) no . .
C16 H9 3.29(2) no . .
B1 H8 2.56(3) no . .
H1 H7 2.53(3) no . .
H2 H3 2.37(3) no . .
H3 H4 2.50(3) no . .
H4 H5 2.34(3) no . .
H5 H6 2.32(3) no . .
H6 H7 2.37(3) no . .
H8 H9 2.37(3) no . .
H9 H10 2.42(3) no . .
H10 H11 2.37(3) no . .
F1 H2 3.33(2) no . 2_665
F1 H3 2.93(2) no . 2_665
F1 H4 3.20(2) no . 1_556
F1 H8 2.90(3) no . 2_666
F1 H9 2.60(2) no . 2_666
F1 H10 2.43(2) no . 1_545
F2 H3 2.60(2) no . 2_565
F2 H4 2.47(2) no . 1_556
F2 H4 3.28(2) no . 2_565
F2 H5 3.59(2) no . 1_556
F2 H5 3.32(2) no . 2_555
F2 H6 2.73(2) no . 2_555
F2 H8 3.34(2) no . 2_566
F2 H10 3.49(2) no . 1_545
O1 H2 3.34(2) no . 2_665
O1 H3 3.52(2) no . 2_565
O1 H6 2.96(2) no . 2_555
O1 H10 3.11(2) no . 1_545
N1 H3 3.55(2) no . 2_665
N1 H4 3.33(2) no . 2_565
N2 H7 3.18(2) no . 1_565
C1 H6 3.58(2) no . 2_555
C1 H7 2.99(2) no . 2_555
C1 H11 3.25(2) no . 1_545
C1 H11 3.46(2) no . 2_665
C3 H6 3.11(2) no . 1_565
C3 H7 3.48(2) no . 1_565
C4 H6 3.16(2) no . 1_565
C4 H8 3.52(2) no . 1_554
C6 H9 3.56(2) no . 2_665
C7 H5 3.28(3) no . 2_554
C7 H9 3.08(2) no . 1_544
C7 H10 3.45(2) no . 2_665
C8 H1 3.11(2) no . 2_555
C8 H2 3.07(2) no . 1_545
C8 H3 3.52(2) no . 1_545
C8 H9 3.52(2) no . 1_544
C8 H10 3.28(2) no . 2_665
C9 H1 2.95(2) no . 2_555
C9 H2 3.13(2) no . 1_545
C9 H7 3.15(2) no . 2_555
C9 H10 3.45(2) no . 2_665
C9 H11 3.57(3) no . 1_545
C9 H11 3.56(3) no . 2_665
C10 H7 3.18(2) no . 2_555
C10 H11 3.35(3) no . 2_665
C11 H2 3.43(2) no . 2_665
C13 H3 3.49(2) no . 1_556
C13 H4 3.32(2) no . 2_565
C13 H8 3.33(2) no . 2_666
C14 H4 3.59(2) no . 2_665
C14 H5 3.11(2) no . 1_566
C14 H5 3.50(3) no . 2_565
C14 H9 3.43(2) no . 2_676
C15 H5 3.40(3) no . 2_565
C15 H9 3.53(2) no . 2_676
C16 H1 3.22(2) no . 1_565
C16 H7 3.58(2) no . 1_565
B1 H3 3.42(2) no . 2_565
B1 H4 3.32(2) no . 1_556
B1 H6 3.37(2) no . 2_555
B1 H10 3.13(2) no . 1_545
H1 C8 3.11(2) no . 2_555
H1 C9 2.95(2) no . 2_555
H1 C16 3.22(2) no . 1_545
H1 H6 2.93(3) no . 2_555
H1 H7 2.67(3) no . 2_555
H1 H10 3.55(3) no . 1_545
H1 H11 2.43(3) no . 1_545
H2 F1 3.33(2) no . 2_665
H2 O1 3.34(2) no . 2_665
H2 C8 3.07(2) no . 1_565
H2 C9 3.13(2) no . 1_565
H2 C11 3.43(2) no . 2_665
H2 H6 2.55(3) no . 1_565
H2 H7 2.58(3) no . 1_565
H3 F1 2.93(2) no . 2_665
H3 F2 2.60(2) no . 2_565
H3 O1 3.52(2) no . 2_565
H3 N1 3.55(2) no . 2_665
H3 C8 3.52(2) no . 1_565
H3 C13 3.49(2) no . 1_554
H3 B1 3.42(2) no . 2_565
H3 H6 2.63(3) no . 1_565
H3 H8 2.65(3) no . 1_554
H4 F1 3.20(2) no . 1_554
H4 F2 2.47(2) no . 1_554
H4 F2 3.28(2) no . 2_565
H4 N1 3.33(2) no . 2_565
H4 C13 3.32(2) no . 2_565
H4 C14 3.59(2) no . 2_665
H4 B1 3.32(2) no . 1_554
H4 H8 2.91(3) no . 1_554
H4 H8 3.53(3) no . 2_565
H4 H9 3.56(3) no . 2_665
H5 F2 3.59(2) no . 1_554
H5 F2 3.32(2) no . 2_555
H5 C7 3.28(3) no . 2_554
H5 C14 3.11(2) no . 1_544
H5 C14 3.50(3) no . 2_565
H5 C15 3.40(3) no . 2_565
H5 H5 2.37(4) no . 2_554
H5 H9 2.66(3) no . 1_544
H5 H10 3.60(3) no . 2_565
H6 F2 2.73(2) no . 2_555
H6 O1 2.96(2) no . 2_555
H6 C1 3.58(2) no . 2_555
H6 C3 3.11(2) no . 1_545
H6 C4 3.16(2) no . 1_545
H6 B1 3.37(2) no . 2_555
H6 H1 2.93(3) no . 2_555
H6 H2 2.55(3) no . 1_545
H6 H3 2.63(3) no . 1_545
H6 H9 3.45(3) no . 1_544
H7 N2 3.18(2) no . 1_545
H7 C1 2.99(2) no . 2_555
H7 C3 3.48(2) no . 1_545
H7 C9 3.15(2) no . 2_555
H7 C10 3.18(2) no . 2_555
H7 C16 3.58(2) no . 1_545
H7 H1 2.67(3) no . 2_555
H7 H2 2.58(3) no . 1_545
H7 H7 2.93(3) no . 2_555
H7 H11 2.83(4) no . 1_545
H8 F1 2.90(3) no . 2_666
H8 F2 3.34(2) no . 2_566
H8 C4 3.52(2) no . 1_556
H8 C13 3.33(2) no . 2_666
H8 H3 2.65(3) no . 1_556
H8 H4 2.91(3) no . 1_556
H8 H4 3.53(3) no . 2_565
H8 H8 2.81(3) no . 2_666
H9 F1 2.60(2) no . 2_666
H9 C6 3.56(2) no . 2_665
H9 C7 3.08(2) no . 1_566
H9 C8 3.52(2) no . 1_566
H9 C14 3.43(2) no . 2_676
H9 C15 3.53(2) no . 2_676
H9 H4 3.56(3) no . 2_665
H9 H5 2.66(3) no . 1_566
H9 H6 3.45(3) no . 1_566
H9 H9 2.79(3) no . 2_676
H9 H10 2.97(3) no . 2_676
H10 F1 2.43(2) no . 1_565
H10 F2 3.49(2) no . 1_565
H10 O1 3.11(2) no . 1_565
H10 C7 3.45(2) no . 2_665
H10 C8 3.28(2) no . 2_665
H10 C9 3.45(2) no . 2_665
H10 B1 3.13(2) no . 1_565
H10 H1 3.55(3) no . 1_565
H10 H5 3.60(3) no . 2_565
H10 H9 2.97(3) no . 2_676
H11 C1 3.25(2) no . 1_565
H11 C1 3.46(2) no . 2_665
H11 C9 3.57(3) no . 1_565
H11 C9 3.56(3) no . 2_665
H11 C10 3.35(3) no . 2_665
H11 H1 2.43(3) no . 1_565
H11 H7 2.83(4) no . 1_565

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.






_publcif_funding_html            
;
;

####################################################################### 
# 
# 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_3-F@py
_database_code_depnum_ccdc_archive 'CCDC 1881149'
loop_
_audit_author_name
_audit_author_address
'Kenta Goto'
;Kyushu University
Japan
;
_audit_update_record             
;
2018-11-26 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H7 B F2 N2 O2'
_chemical_formula_moiety         'C10 H7 B F2 N2 O2'
_chemical_formula_weight         235.98
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.1853(4)
_cell_length_b                   26.0241(9)
_cell_length_c                   7.1318(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.872(8)
_cell_angle_gamma                90.0000
_cell_volume                     1996.83(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7654
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.18
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960.00
_exptl_absorpt_coefficient_mu    1.162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_T_max  0.955

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            13554
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_theta_max         68.182
_diffrn_reflns_theta_min         3.397
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3577
_reflns_number_gt                1710
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.0964
_refine_ls_wR_factor_ref         0.2904
_refine_ls_wR_factor_gt          0.2376
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3577
_refine_ls_number_parameters     307
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1458P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F2 F -0.0343(3) 0.62331(10) 0.3950(4) 0.0591(9) Uani 1 1 d . . . . .
F5 F 0.4714(3) 0.87473(10) 0.2850(5) 0.0628(10) Uani 1 1 d . . . . .
F25 F 0.4032(3) 0.87486(10) 0.5560(5) 0.0640(10) Uani 1 1 d . . . . .
F28 F 0.0409(3) 0.62216(10) 0.1310(5) 0.0588(9) Uani 1 1 d . . . . .
O1 O 0.5595(3) 0.81781(13) 0.5358(5) 0.0504(10) Uani 1 1 d . . . . .
O3 O 0.8839(3) 0.74207(14) 0.8301(5) 0.0555(11) Uani 1 1 d . . . . .
O32 O 0.1195(3) 0.56437(13) 0.3843(5) 0.0490(10) Uani 1 1 d . . . . .
O35 O 0.4426(3) 0.48384(15) 0.6632(5) 0.0579(11) Uani 1 1 d . . . . .
N6 N -0.0933(4) 0.55327(15) 0.1691(6) 0.0437(11) Uani 1 1 d . . . . .
N7 N 0.3443(4) 0.80456(15) 0.3349(6) 0.0424(11) Uani 1 1 d . . . . .
N10 N 0.0427(4) 0.48271(15) 0.2815(6) 0.0464(11) Uani 1 1 d . . . . .
N11 N 0.4796(4) 0.73512(15) 0.4611(6) 0.0442(11) Uani 1 1 d . . . . .
C8 C 0.3974(5) 0.4363(2) 0.6129(8) 0.0578(16) Uani 1 1 d . . . . .
H8 H 0.4424 0.4053 0.6502 0.069 Uiso 1 1 calc R U . . .
C9 C 0.7894(4) 0.7740(2) 0.7456(8) 0.0512(15) Uani 1 1 d . . . . .
H9 H 0.7942 0.8104 0.7498 0.061 Uiso 1 1 calc R U . . .
C12 C -0.2999(5) 0.5392(2) -0.0269(7) 0.0490(14) Uani 1 1 d . . . . .
H12 H -0.3788 0.5524 -0.0965 0.059 Uiso 1 1 calc R U . . .
C13 C 0.3655(4) 0.75312(18) 0.3563(7) 0.0403(13) Uani 1 1 d . . . . .
C14 C 0.1290(5) 0.5138(2) 0.3743(7) 0.0429(14) Uani 1 1 d . . . . .
C15 C -0.0705(5) 0.5021(2) 0.1787(7) 0.0437(13) Uani 1 1 d . . . . .
C16 C 0.5673(4) 0.76731(19) 0.5430(7) 0.0402(13) Uani 1 1 d . . . . .
C17 C -0.1635(5) 0.4687(2) 0.0828(8) 0.0463(14) Uani 1 1 d . . . . .
H17 H -0.1481 0.4327 0.0875 0.056 Uiso 1 1 calc R U . . .
C18 C 0.2472(5) 0.4919(2) 0.4823(8) 0.0452(14) Uani 1 1 d . . . . .
C19 C 0.6871(5) 0.7470(2) 0.6544(8) 0.0443(13) Uani 1 1 d . . . . .
C20 C 0.7196(5) 0.6940(2) 0.6833(7) 0.0453(13) Uani 1 1 d . . . . .
H20 H 0.6671 0.6654 0.6363 0.054 Uiso 1 1 calc R U . . .
C21 C 0.2303(5) 0.8212(2) 0.2323(7) 0.0465(14) Uani 1 1 d . . . . .
H21 H 0.2168 0.8572 0.2147 0.056 Uiso 1 1 calc R U . . .
C22 C -0.2069(5) 0.5714(2) 0.0670(7) 0.0503(15) Uani 1 1 d . . . . .
H22 H -0.2214 0.6075 0.0613 0.060 Uiso 1 1 calc R U . . .
C23 C 0.2710(5) 0.71891(19) 0.2760(8) 0.0463(14) Uani 1 1 d . . . . .
H23 H 0.2863 0.6830 0.2912 0.056 Uiso 1 1 calc R U . . .
C24 C 0.1562(5) 0.7359(2) 0.1754(8) 0.0471(14) Uani 1 1 d . . . . .
H24 H 0.0916 0.7121 0.1207 0.057 Uiso 1 1 calc R U . . .
C29 C 0.8395(5) 0.6925(2) 0.7904(7) 0.0503(14) Uani 1 1 d . . . . .
H29 H 0.8862 0.6621 0.8321 0.060 Uiso 1 1 calc R U . . .
C30 C 0.3497(5) 0.5178(2) 0.5809(8) 0.0513(15) Uani 1 1 d . . . . .
H30 H 0.3563 0.5542 0.5915 0.062 Uiso 1 1 calc R U . . .
C31 C 0.2780(5) 0.4393(2) 0.5012(8) 0.0526(15) Uani 1 1 d . . . . .
H31 H 0.2254 0.4114 0.4463 0.063 Uiso 1 1 calc R U . . .
C33 C -0.2775(5) 0.4870(2) -0.0188(8) 0.0497(15) Uani 1 1 d . . . . .
H33 H -0.3410 0.4639 -0.0837 0.060 Uiso 1 1 calc R U . . .
C34 C 0.1347(4) 0.7888(2) 0.1537(7) 0.0461(14) Uani 1 1 d . . . . .
H34 H 0.0553 0.8017 0.0857 0.055 Uiso 1 1 calc R U . . .
B26 B 0.4475(5) 0.8449(3) 0.4292(10) 0.0498(17) Uani 1 1 d . . . . .
B27 B 0.0102(6) 0.5926(3) 0.2732(10) 0.0516(18) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
F2 B27 1.371(7) . ?
F5 B26 1.372(7) . ?
F25 B26 1.385(7) . ?
F28 B27 1.389(7) . ?
O1 C16 1.317(5) . ?
O1 B26 1.457(6) . ?
O3 C9 1.350(5) . ?
O3 C29 1.384(6) . ?
O32 C14 1.324(5) . ?
O32 B27 1.460(7) . ?
O35 C8 1.348(6) . ?
O35 C30 1.369(6) . ?
N6 C15 1.355(6) . ?
N6 C22 1.365(6) . ?
N6 B27 1.571(7) . ?
N7 C21 1.356(5) . ?
N7 C13 1.361(5) . ?
N7 B26 1.568(7) . ?
N10 C14 1.293(6) . ?
N10 C15 1.374(6) . ?
N11 C16 1.301(6) . ?
N11 C13 1.373(6) . ?
C8 C31 1.357(7) . ?
C8 H8 0.9500 . ?
C9 C19 1.348(7) . ?
C9 H9 0.9500 . ?
C12 C22 1.362(6) . ?
C12 C33 1.380(6) . ?
C12 H12 0.9500 . ?
C13 C23 1.381(6) . ?
C14 C18 1.452(7) . ?
C15 C17 1.385(6) . ?
C16 C19 1.458(6) . ?
C17 C33 1.369(6) . ?
C17 H17 0.9500 . ?
C18 C30 1.349(7) . ?
C18 C31 1.410(6) . ?
C19 C20 1.425(6) . ?
C20 C29 1.351(6) . ?
C20 H20 0.9500 . ?
C21 C34 1.357(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.361(6) . ?
C23 H23 0.9500 . ?
C24 C34 1.400(6) . ?
C24 H24 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

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
C16 O1 B26 122.8(4) . . ?
C9 O3 C29 106.8(4) . . ?
C14 O32 B27 122.5(4) . . ?
C8 O35 C30 107.1(4) . . ?
C15 N6 C22 120.2(4) . . ?
C15 N6 B27 120.8(4) . . ?
C22 N6 B27 119.0(5) . . ?
C21 N7 C13 119.0(4) . . ?
C21 N7 B26 119.4(4) . . ?
C13 N7 B26 121.6(4) . . ?
C14 N10 C15 119.5(5) . . ?
C16 N11 C13 120.0(4) . . ?
O35 C8 C31 109.9(5) . . ?
O35 C8 H8 125.1 . . ?
C31 C8 H8 125.1 . . ?
C19 C9 O3 110.6(5) . . ?
C19 C9 H9 124.7 . . ?
O3 C9 H9 124.7 . . ?
C22 C12 C33 118.7(5) . . ?
C22 C12 H12 120.7 . . ?
C33 C12 H12 120.7 . . ?
N7 C13 N11 120.3(4) . . ?
N7 C13 C23 119.8(5) . . ?
N11 C13 C23 119.9(5) . . ?
N10 C14 O32 126.1(5) . . ?
N10 C14 C18 118.1(5) . . ?
O32 C14 C18 115.8(4) . . ?
N6 C15 N10 121.4(5) . . ?
N6 C15 C17 119.1(5) . . ?
N10 C15 C17 119.5(5) . . ?
N11 C16 O1 126.2(5) . . ?
N11 C16 C19 118.6(5) . . ?
O1 C16 C19 115.2(4) . . ?
C33 C17 C15 120.5(5) . . ?
C33 C17 H17 119.7 . . ?
C15 C17 H17 119.7 . . ?
C30 C18 C31 106.5(5) . . ?
C30 C18 C14 127.0(5) . . ?
C31 C18 C14 126.5(5) . . ?
C9 C19 C20 106.6(5) . . ?
C9 C19 C16 127.3(5) . . ?
C20 C19 C16 126.1(5) . . ?
C29 C20 C19 106.5(5) . . ?
C29 C20 H20 126.7 . . ?
C19 C20 H20 126.7 . . ?
N7 C21 C34 122.9(5) . . ?
N7 C21 H21 118.6 . . ?
C34 C21 H21 118.6 . . ?
C12 C22 N6 121.6(5) . . ?
C12 C22 H22 119.2 . . ?
N6 C22 H22 119.2 . . ?
C24 C23 C13 120.9(5) . . ?
C24 C23 H23 119.5 . . ?
C13 C23 H23 119.5 . . ?
C23 C24 C34 119.1(5) . . ?
C23 C24 H24 120.5 . . ?
C34 C24 H24 120.5 . . ?
C20 C29 O3 109.5(4) . . ?
C20 C29 H29 125.3 . . ?
O3 C29 H29 125.3 . . ?
C18 C30 O35 109.7(5) . . ?
C18 C30 H30 125.1 . . ?
O35 C30 H30 125.1 . . ?
C8 C31 C18 106.7(5) . . ?
C8 C31 H31 126.6 . . ?
C18 C31 H31 126.6 . . ?
C17 C33 C12 119.9(5) . . ?
C17 C33 H33 120.1 . . ?
C12 C33 H33 120.1 . . ?
C21 C34 C24 118.3(5) . . ?
C21 C34 H34 120.9 . . ?
C24 C34 H34 120.9 . . ?
F5 B26 F25 110.4(5) . . ?
F5 B26 O1 110.4(5) . . ?
F25 B26 O1 110.0(5) . . ?
F5 B26 N7 109.2(5) . . ?
F25 B26 N7 107.7(4) . . ?
O1 B26 N7 109.1(5) . . ?
F2 B27 F28 110.1(5) . . ?
F2 B27 O32 110.2(5) . . ?
F28 B27 O32 109.7(5) . . ?
F2 B27 N6 109.3(4) . . ?
F28 B27 N6 108.3(5) . . ?
O32 B27 N6 109.2(5) . . ?

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
C30 O35 C8 C31 -0.1(6) . . . . ?
C29 O3 C9 C19 0.1(6) . . . . ?
C21 N7 C13 N11 -179.3(4) . . . . ?
B26 N7 C13 N11 -0.5(7) . . . . ?
C21 N7 C13 C23 -0.8(7) . . . . ?
B26 N7 C13 C23 178.0(5) . . . . ?
C16 N11 C13 N7 1.1(7) . . . . ?
C16 N11 C13 C23 -177.4(5) . . . . ?
C15 N10 C14 O32 1.1(8) . . . . ?
C15 N10 C14 C18 179.6(4) . . . . ?
B27 O32 C14 N10 -5.9(8) . . . . ?
B27 O32 C14 C18 175.6(5) . . . . ?
C22 N6 C15 N10 -179.6(4) . . . . ?
B27 N6 C15 N10 0.9(7) . . . . ?
C22 N6 C15 C17 0.4(7) . . . . ?
B27 N6 C15 C17 -179.1(5) . . . . ?
C14 N10 C15 N6 1.3(7) . . . . ?
C14 N10 C15 C17 -178.7(5) . . . . ?
C13 N11 C16 O1 -0.5(8) . . . . ?
C13 N11 C16 C19 179.6(4) . . . . ?
B26 O1 C16 N11 -0.7(8) . . . . ?
B26 O1 C16 C19 179.2(5) . . . . ?
N6 C15 C17 C33 -0.7(8) . . . . ?
N10 C15 C17 C33 179.3(5) . . . . ?
N10 C14 C18 C30 177.0(5) . . . . ?
O32 C14 C18 C30 -4.4(8) . . . . ?
N10 C14 C18 C31 -1.6(8) . . . . ?
O32 C14 C18 C31 177.1(5) . . . . ?
O3 C9 C19 C20 -0.1(6) . . . . ?
O3 C9 C19 C16 -178.5(4) . . . . ?
N11 C16 C19 C9 178.5(5) . . . . ?
O1 C16 C19 C9 -1.4(8) . . . . ?
N11 C16 C19 C20 0.4(8) . . . . ?
O1 C16 C19 C20 -179.6(4) . . . . ?
C9 C19 C20 C29 0.1(6) . . . . ?
C16 C19 C20 C29 178.5(5) . . . . ?
C13 N7 C21 C34 1.8(7) . . . . ?
B26 N7 C21 C34 -177.1(5) . . . . ?
C33 C12 C22 N6 -0.5(8) . . . . ?
C15 N6 C22 C12 0.2(7) . . . . ?
B27 N6 C22 C12 179.7(5) . . . . ?
N7 C13 C23 C24 -0.1(8) . . . . ?
N11 C13 C23 C24 178.4(4) . . . . ?
C13 C23 C24 C34 0.1(7) . . . . ?
C19 C20 C29 O3 0.0(6) . . . . ?
C9 O3 C29 C20 0.0(6) . . . . ?
C31 C18 C30 O35 -1.0(6) . . . . ?
C14 C18 C30 O35 -179.7(5) . . . . ?
C8 O35 C30 C18 0.7(6) . . . . ?
O35 C8 C31 C18 -0.5(6) . . . . ?
C30 C18 C31 C8 0.9(6) . . . . ?
C14 C18 C31 C8 179.7(5) . . . . ?
C15 C17 C33 C12 0.4(8) . . . . ?
C22 C12 C33 C17 0.2(8) . . . . ?
N7 C21 C34 C24 -1.8(8) . . . . ?
C23 C24 C34 C21 0.8(7) . . . . ?
C16 O1 B26 F5 -118.9(5) . . . . ?
C16 O1 B26 F25 119.1(5) . . . . ?
C16 O1 B26 N7 1.1(7) . . . . ?
C21 N7 B26 F5 -60.9(6) . . . . ?
C13 N7 B26 F5 120.3(5) . . . . ?
C21 N7 B26 F25 58.9(6) . . . . ?
C13 N7 B26 F25 -119.9(5) . . . . ?
C21 N7 B26 O1 178.3(4) . . . . ?
C13 N7 B26 O1 -0.5(7) . . . . ?
C14 O32 B27 F2 127.1(5) . . . . ?
C14 O32 B27 F28 -111.5(5) . . . . ?
C14 O32 B27 N6 7.0(7) . . . . ?
C15 N6 B27 F2 -125.3(5) . . . . ?
C22 N6 B27 F2 55.2(7) . . . . ?
C15 N6 B27 F28 114.7(5) . . . . ?
C22 N6 B27 F28 -64.8(6) . . . . ?
C15 N6 B27 O32 -4.7(7) . . . . ?
C22 N6 B27 O32 175.8(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





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

data_2-F@py
_database_code_depnum_ccdc_archive 'CCDC 1881148'
loop_
_audit_author_name
_audit_author_address
'Kenta Goto'
;Kyushu University
Japan
;
_audit_update_record             
;
2018-11-26 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H7 B F2 N2 O2'
_chemical_formula_moiety         'C10 H7 B F2 N2 O2'
_chemical_formula_weight         235.98
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.1941(3)
_cell_length_b                   8.5967(4)
_cell_length_c                   9.1402(4)
_cell_angle_alpha                88.519(6)
_cell_angle_beta                 70.424(5)
_cell_angle_gamma                67.994(5)
_cell_volume                     490.57(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5579
_cell_measurement_theta_min      5.17
_cell_measurement_theta_max      68.28
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240.00
_exptl_absorpt_coefficient_mu    1.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_T_max  0.889

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            5873
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_theta_max         68.182
_diffrn_reflns_theta_min         5.170
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1767
_reflns_number_gt                1576
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.2008
_refine_ls_wR_factor_gt          0.1940
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1767
_refine_ls_number_parameters     154
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1235P)²+0.7188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.64
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.0249(3) 0.8511(2) 0.6774(2) 0.0399(5) Uani 1 2 d . . .
F2 F 0.3299(3) 0.6871(2) 0.5790(2) 0.0419(6) Uani 1 2 d . . .
O1 O 0.2900(4) 0.6727(3) 1.1928(3) 0.0459(7) Uani 1 2 d . . .
O2 O 0.1510(3) 0.7245(3) 0.8474(2) 0.0276(5) Uani 1 2 d . . .
N1 N 0.2965(4) 0.8813(3) 0.9457(3) 0.0257(6) Uani 1 2 d . . .
N2 N 0.2228(4) 0.9593(3) 0.7136(3) 0.0235(6) Uani 1 2 d . . .
C1 C 0.2319(4) 0.6526(4) 1.0712(3) 0.0233(6) Uani 1 2 d . . .
C2 C 0.2752(5) 0.5398(4) 1.2813(4) 0.0357(8) Uani 1 2 d . . .
C3 C 0.2150(5) 0.4440(4) 1.2111(4) 0.0345(7) Uani 1 2 d . . .
C4 C 0.1868(4) 0.5135(3) 1.0759(3) 0.0169(5) Uani 1 2 d . . .
C5 C 0.2283(4) 0.7609(3) 0.9472(3) 0.0228(6) Uani 1 2 d . . .
C6 C 0.2879(4) 0.9857(3) 0.8293(3) 0.0231(6) Uani 1 2 d . . .
C7 C 0.3460(5) 1.1233(4) 0.8329(4) 0.0303(7) Uani 1 2 d . . .
C8 C 0.3330(5) 1.2314(4) 0.7197(4) 0.0310(7) Uani 1 2 d . . .
C9 C 0.2640(5) 1.2028(4) 0.6026(4) 0.0334(7) Uani 1 2 d . . .
C10 C 0.2107(5) 1.0654(4) 0.6019(3) 0.0308(7) Uani 1 2 d . . .
B1 B 0.1665(5) 0.8005(4) 0.7012(4) 0.0273(7) Uani 1 2 d . . .
H1 H 0.30345 0.52125 1.37598 0.0428 Uiso 1 2 calc R . .
H2 H 0.19455 0.34474 1.24648 0.0413 Uiso 1 2 calc R . .
H3 H 0.14447 0.47133 1.00273 0.0203 Uiso 1 2 calc R . .
H4 H 0.39422 1.14198 0.91319 0.0363 Uiso 1 2 calc R . .
H5 H 0.37128 1.32553 0.72196 0.0372 Uiso 1 2 calc R . .
H6 H 0.25366 1.27691 0.52405 0.0401 Uiso 1 2 calc R . .
H7 H 0.16436 1.04433 0.52142 0.0370 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 B1 1.371(5) yes . .
F2 B1 1.377(3) yes . .
O1 C1 1.347(5) yes . .
O1 C2 1.399(4) yes . .
O2 C5 1.313(4) yes . .
O2 B1 1.461(4) yes . .
N1 C5 1.300(5) yes . .
N1 C6 1.377(4) yes . .
N2 C6 1.347(4) yes . .
N2 C10 1.354(4) yes . .
N2 B1 1.579(5) yes . .
C1 C4 1.348(4) yes . .
C1 C5 1.448(4) yes . .
C2 C3 1.326(6) yes . .
C3 C4 1.402(4) yes . .
C6 C7 1.399(5) yes . .
C7 C8 1.376(4) yes . .
C8 C9 1.384(6) yes . .
C9 C10 1.372(5) yes . .
C2 H1 0.950 no . .
C3 H2 0.950 no . .
C4 H3 0.950 no . .
C7 H4 0.950 no . .
C8 H5 0.950 no . .
C9 H6 0.950 no . .
C10 H7 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 O1 C2 105.9(3) yes . . .
C5 O2 B1 121.9(3) yes . . .
C5 N1 C6 118.4(3) yes . . .
C6 N2 C10 120.7(3) yes . . .
C6 N2 B1 120.9(2) yes . . .
C10 N2 B1 118.3(3) yes . . .
O1 C1 C4 111.0(3) yes . . .
O1 C1 C5 124.8(3) yes . . .
C4 C1 C5 124.1(3) yes . . .
O1 C2 C3 108.7(3) yes . . .
C2 C3 C4 108.6(3) yes . . .
C1 C4 C3 105.8(3) yes . . .
O2 C5 N1 127.1(3) yes . . .
O2 C5 C1 114.0(3) yes . . .
N1 C5 C1 118.9(3) yes . . .
N1 C6 N2 121.5(3) yes . . .
N1 C6 C7 118.9(3) yes . . .
N2 C6 C7 119.6(3) yes . . .
C6 C7 C8 119.7(3) yes . . .
C7 C8 C9 119.9(3) yes . . .
C8 C9 C10 118.7(3) yes . . .
N2 C10 C9 121.4(3) yes . . .
F1 B1 F2 111.2(3) yes . . .
F1 B1 O2 110.2(3) yes . . .
F1 B1 N2 109.3(2) yes . . .
F2 B1 O2 109.8(2) yes . . .
F2 B1 N2 108.1(3) yes . . .
O2 B1 N2 108.2(3) yes . . .
O1 C2 H1 125.673 no . . .
C3 C2 H1 125.666 no . . .
C2 C3 H2 125.676 no . . .
C4 C3 H2 125.677 no . . .
C1 C4 H3 127.120 no . . .
C3 C4 H3 127.125 no . . .
C6 C7 H4 120.167 no . . .
C8 C7 H4 120.165 no . . .
C7 C8 H5 120.071 no . . .
C9 C8 H5 120.058 no . . .
C8 C9 H6 120.644 no . . .
C10 C9 H6 120.625 no . . .
N2 C10 H7 119.284 no . . .
C9 C10 H7 119.275 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 O1 C2 C3 1.3(3) no . . . .
C2 O1 C1 C4 -1.5(3) no . . . .
C2 O1 C1 C5 -178.67(19) no . . . .
C5 O2 B1 F1 -135.5(2) no . . . .
C5 O2 B1 F2 101.7(3) no . . . .
C5 O2 B1 N2 -16.1(3) no . . . .
B1 O2 C5 N1 11.0(3) no . . . .
B1 O2 C5 C1 -169.80(17) no . . . .
C5 N1 C6 N2 -3.9(3) no . . . .
C5 N1 C6 C7 175.35(17) no . . . .
C6 N1 C5 O2 0.5(3) no . . . .
C6 N1 C5 C1 -178.61(16) no . . . .
C6 N2 C10 C9 0.0(3) no . . . .
C10 N2 C6 N1 178.49(18) no . . . .
C10 N2 C6 C7 -0.7(3) no . . . .
C6 N2 B1 F1 132.8(2) no . . . .
C6 N2 B1 F2 -106.1(3) no . . . .
C6 N2 B1 O2 12.8(3) no . . . .
B1 N2 C6 N1 -3.7(3) no . . . .
B1 N2 C6 C7 177.08(17) no . . . .
C10 N2 B1 F1 -49.3(3) no . . . .
C10 N2 B1 F2 71.8(3) no . . . .
C10 N2 B1 O2 -169.37(19) no . . . .
B1 N2 C10 C9 -177.88(19) no . . . .
O1 C1 C4 C3 1.1(2) no . . . .
O1 C1 C5 O2 -175.18(19) no . . . .
O1 C1 C5 N1 4.1(3) no . . . .
C4 C1 C5 O2 8.0(3) no . . . .
C4 C1 C5 N1 -172.77(19) no . . . .
C5 C1 C4 C3 178.27(19) no . . . .
O1 C2 C3 C4 -0.7(3) no . . . .
C2 C3 C4 C1 -0.2(3) no . . . .
N1 C6 C7 C8 -178.30(18) no . . . .
N2 C6 C7 C8 1.0(3) no . . . .
C6 C7 C8 C9 -0.4(4) no . . . .
C7 C8 C9 C10 -0.3(4) no . . . .
C8 C9 C10 N2 0.5(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 C5 3.443(4) no . .
F1 C6 3.530(4) no . .
F1 C10 2.870(4) no . .
F2 C5 3.221(3) no . .
F2 C6 3.343(4) no . .
F2 C10 3.031(4) no . .
O1 O2 3.588(4) no . .
O1 N1 2.847(4) no . .
O2 C4 2.744(3) no . .
O2 C6 2.752(4) no . .
N1 B1 2.884(5) no . .
N2 C5 2.700(4) no . .
N2 C8 2.744(5) no . .
C3 C5 3.598(4) no . .
C5 C7 3.568(5) no . .
C6 C9 2.758(4) no . .
C7 C10 2.729(5) no . .
F1 C3 3.298(4) no . 2_567
F1 C10 3.208(4) no . 2_576
F2 F2 3.224(2) no . 2_666
F2 C2 3.230(4) no . 1_554
F2 C2 3.414(4) no . 2_667
F2 C8 3.251(4) no . 2_676
F2 C9 3.306(4) no . 2_676
O1 C4 3.501(3) no . 2_667
O1 C8 3.441(5) no . 2_677
O1 C9 3.527(4) no . 2_577
O1 C10 3.343(3) no . 2_577
O2 C7 3.567(3) no . 2_577
N1 C3 3.419(3) no . 2_667
C1 C1 3.561(3) no . 2_667
C1 C9 3.593(3) no . 2_577
C2 F2 3.230(4) no . 1_556
C2 F2 3.414(4) no . 2_667
C2 C5 3.487(3) no . 2_667
C2 C9 3.464(4) no . 2_577
C3 F1 3.298(4) no . 2_567
C3 N1 3.419(3) no . 2_667
C3 C5 3.492(4) no . 2_667
C3 C9 3.534(3) no . 2_577
C4 O1 3.501(3) no . 2_667
C4 C4 3.490(4) no . 2_567
C4 C8 3.415(3) no . 2_577
C5 C2 3.487(3) no . 2_667
C5 C3 3.492(4) no . 2_667
C5 C6 3.434(3) no . 2_577
C6 C5 3.434(3) no . 2_577
C7 O2 3.567(3) no . 2_577
C8 F2 3.251(4) no . 2_676
C8 O1 3.441(5) no . 2_677
C8 C4 3.415(3) no . 2_577
C9 F2 3.306(4) no . 2_676
C9 O1 3.527(4) no . 2_577
C9 C1 3.593(3) no . 2_577
C9 C2 3.464(4) no . 2_577
C9 C3 3.534(3) no . 2_577
C9 C10 3.472(4) no . 2_676
C10 F1 3.208(4) no . 2_576
C10 O1 3.343(3) no . 2_577
C10 C9 3.472(4) no . 2_676
F1 H7 2.6301 no . .
F2 H7 2.9536 no . .
O1 H2 3.1326 no . .
O1 H3 3.1372 no . .
O2 H3 2.5741 no . .
N1 H4 2.5709 no . .
N2 H4 3.2286 no . .
N2 H6 3.2339 no . .
C1 H1 3.1089 no . .
C1 H2 3.1098 no . .
C2 H3 3.1319 no . .
C4 H1 3.1349 no . .
C5 H3 2.7696 no . .
C6 H5 3.2597 no . .
C6 H7 3.1981 no . .
C7 H6 3.2501 no . .
C8 H7 3.2294 no . .
C9 H4 3.2483 no . .
C10 H5 3.2325 no . .
B1 H7 2.6287 no . .
H1 H2 2.4336 no . .
H2 H3 2.5291 no . .
H4 H5 2.3298 no . .
H5 H6 2.3437 no . .
H6 H7 2.3209 no . .
F1 H1 3.4973 no . 1_554
F1 H2 2.3913 no . 2_567
F1 H6 3.2863 no . 2_576
F1 H7 2.3616 no . 2_576
F2 H1 2.4673 no . 1_554
F2 H1 2.7357 no . 2_667
F2 H5 3.2882 no . 1_545
F2 H5 2.8425 no . 2_676
F2 H6 2.9580 no . 2_676
O1 H3 3.5701 no . 2_667
O1 H4 3.1299 no . 2_677
O1 H5 2.8011 no . 2_677
O1 H7 3.4748 no . 2_577
O2 H1 3.5599 no . 2_667
O2 H2 3.1360 no . 2_567
O2 H3 3.1368 no . 2_567
O2 H4 3.5350 no . 2_577
O2 H5 3.2403 no . 1_545
N1 H2 3.2867 no . 2_667
N1 H4 2.8686 no . 2_677
N2 H6 3.4699 no . 2_676
C1 H3 3.5142 no . 2_567
C2 H5 3.1569 no . 2_677
C2 H6 3.1348 no . 1_546
C2 H6 3.3524 no . 2_577
C3 H3 3.5973 no . 2_567
C3 H4 3.3646 no . 1_545
C3 H6 3.2164 no . 1_546
C3 H6 3.4285 no . 2_577
C4 H3 2.6685 no . 2_567
C4 H4 3.1346 no . 1_545
C4 H5 3.2593 no . 1_545
C4 H5 3.5275 no . 2_577
C6 H2 3.5860 no . 2_667
C7 H3 2.9907 no . 1_565
C8 H3 2.9349 no . 1_565
C8 H3 3.5612 no . 2_577
C8 H7 3.4726 no . 2_676
C9 H1 3.4290 no . 1_564
C9 H2 3.5718 no . 1_564
B1 H1 3.4934 no . 1_554
B1 H2 3.1782 no . 2_567
B1 H7 3.5089 no . 2_576
H1 F1 3.4973 no . 1_556
H1 F2 2.4673 no . 1_556
H1 F2 2.7357 no . 2_667
H1 O2 3.5599 no . 2_667
H1 C9 3.4290 no . 1_546
H1 B1 3.4934 no . 1_556
H1 H5 2.9761 no . 2_677
H1 H6 2.5425 no . 1_546
H1 H6 3.5107 no . 2_577
H2 F1 2.3913 no . 2_567
H2 O2 3.1360 no . 2_567
H2 N1 3.2867 no . 2_667
H2 C6 3.5860 no . 2_667
H2 C9 3.5718 no . 1_546
H2 B1 3.1782 no . 2_567
H2 H4 3.1381 no . 1_545
H2 H6 2.7236 no . 1_546
H2 H7 3.5709 no . 1_546
H3 O1 3.5701 no . 2_667
H3 O2 3.1368 no . 2_567
H3 C1 3.5142 no . 2_567
H3 C3 3.5973 no . 2_567
H3 C4 2.6685 no . 2_567
H3 C7 2.9907 no . 1_545
H3 C8 2.9349 no . 1_545
H3 C8 3.5612 no . 2_577
H3 H3 1.9664 no . 2_567
H3 H4 2.6901 no . 1_545
H3 H5 2.5782 no . 1_545
H3 H5 3.5019 no . 2_577
H4 O1 3.1299 no . 2_677
H4 O2 3.5350 no . 2_577
H4 N1 2.8686 no . 2_677
H4 C3 3.3646 no . 1_565
H4 C4 3.1346 no . 1_565
H4 H2 3.1381 no . 1_565
H4 H3 2.6901 no . 1_565
H4 H4 3.0705 no . 2_677
H5 F2 3.2882 no . 1_565
H5 F2 2.8425 no . 2_676
H5 O1 2.8011 no . 2_677
H5 O2 3.2403 no . 1_565
H5 C2 3.1569 no . 2_677
H5 C4 3.2593 no . 1_565
H5 C4 3.5275 no . 2_577
H5 H1 2.9761 no . 2_677
H5 H3 2.5782 no . 1_565
H5 H3 3.5019 no . 2_577
H6 F1 3.2863 no . 2_576
H6 F2 2.9580 no . 2_676
H6 N2 3.4699 no . 2_676
H6 C2 3.1348 no . 1_564
H6 C2 3.3524 no . 2_577
H6 C3 3.2164 no . 1_564
H6 C3 3.4285 no . 2_577
H6 H1 2.5425 no . 1_564
H6 H1 3.5107 no . 2_577
H6 H2 2.7236 no . 1_564
H7 F1 2.3616 no . 2_576
H7 O1 3.4748 no . 2_577
H7 C8 3.4726 no . 2_676
H7 B1 3.5089 no . 2_576
H7 H2 3.5709 no . 1_564
H7 H7 2.8833 no . 2_576

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.






_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_Ph@IQ
_database_code_depnum_ccdc_archive 'CCDC 1881151'
loop_
_audit_author_name
_audit_author_address
'Kenta Goto'
;Kyushu University
Japan
;
_audit_update_record             
;
2018-11-26 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H11 B F2 N2 O'
_chemical_formula_moiety         'C16 H11 B F2 N2 O'
_chemical_formula_weight         296.08
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
_space_group_IT_number           7
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.2084(2)
_cell_length_b                   10.4274(4)
_cell_length_c                   17.7519(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.312(7)
_cell_angle_gamma                90.0000
_cell_volume                     1330.54(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13022
_cell_measurement_theta_min      4.24
_cell_measurement_theta_max      68.28
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608.00
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  0.954

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15104
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_theta_max         68.210
_diffrn_reflns_theta_min         4.240
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4483
_reflns_number_gt                3752
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.840
_reflns_Friedel_fraction_full    0.842

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0948
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4483
_refine_ls_number_parameters     397
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0529P)²+0.1375P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1368 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F1 F -0.1867(4) 0.5322(2) 0.41048(14) 0.0552(8) Uani 1 1 d . . . . .
F2 F 0.1110(4) 0.4633(2) 0.41951(15) 0.0587(8) Uani 1 1 d . . . . .
F3 F 0.4241(3) -0.1168(2) 0.15474(12) 0.0416(6) Uani 1 1 d . . . . .
F4 F 0.1230(3) -0.0551(2) 0.14473(13) 0.0466(7) Uani 1 1 d . . . . .
O1 O -0.0464(4) 0.4811(3) 0.30107(15) 0.0366(7) Uani 1 1 d . . . . .
O2 O 0.3528(4) 0.0967(3) 0.17621(14) 0.0411(8) Uani 1 1 d . . . . .
N1 N -0.0971(4) 0.2723(3) 0.25780(17) 0.0309(8) Uani 1 1 d . . . . .
N2 N -0.1291(5) 0.3097(3) 0.38779(16) 0.0297(8) Uani 1 1 d . . . . .
N3 N 0.3300(4) 0.1503(3) 0.30252(17) 0.0302(8) Uani 1 1 d . . . . .
N4 N 0.2789(4) -0.0664(3) 0.26872(17) 0.0312(8) Uani 1 1 d . . . . .
C1 C -0.0596(5) 0.3927(4) 0.2476(2) 0.0298(9) Uani 1 1 d . . . . .
C2 C -0.1349(5) 0.2307(4) 0.3279(2) 0.0276(9) Uani 1 1 d . . . . .
C3 C -0.1859(5) 0.0989(4) 0.3371(2) 0.0298(9) Uani 1 1 d . . . . .
C4 C -0.1870(6) 0.0119(4) 0.2763(2) 0.0351(10) Uani 1 1 d . . . . .
H4 H -0.1574 0.0404 0.2278 0.042 Uiso 1 1 calc R U . . .
C5 C -0.2313(6) -0.1145(4) 0.2877(3) 0.0418(11) Uani 1 1 d . . . . .
H5 H -0.2316 -0.1734 0.2469 0.050 Uiso 1 1 calc R U . . .
C6 C -0.2757(6) -0.1571(4) 0.3585(3) 0.0444(11) Uani 1 1 d . . . . .
H6 H -0.3041 -0.2450 0.3655 0.053 Uiso 1 1 calc R U . . .
C7 C -0.2792(6) -0.0744(4) 0.4180(3) 0.0372(10) Uani 1 1 d . . . . .
H7 H -0.3122 -0.1045 0.4657 0.045 Uiso 1 1 calc R U . . .
C8 C -0.2335(6) 0.0561(4) 0.4085(2) 0.0321(10) Uani 1 1 d . . . . .
C9 C -0.2291(6) 0.1455(4) 0.4688(2) 0.0354(10) Uani 1 1 d . . . . .
H9 H -0.2634 0.1197 0.5172 0.043 Uiso 1 1 calc R U . . .
C10 C -0.1760(5) 0.2672(4) 0.4571(2) 0.0358(10) Uani 1 1 d . . . . .
H10 H -0.1708 0.3258 0.4982 0.043 Uiso 1 1 calc R U . . .
C11 C -0.0365(6) 0.4419(4) 0.1716(2) 0.0323(10) Uani 1 1 d . . . . .
C12 C -0.0333(6) 0.3577(4) 0.1107(2) 0.0363(10) Uani 1 1 d . . . . .
H12 H -0.0419 0.2679 0.1188 0.044 Uiso 1 1 calc R U . . .
C13 C -0.0178(7) 0.4046(5) 0.0389(2) 0.0438(11) Uani 1 1 d . . . . .
H13 H -0.0141 0.3467 -0.0023 0.053 Uiso 1 1 calc R U . . .
C14 C -0.0076(6) 0.5353(5) 0.0263(3) 0.0468(12) Uani 1 1 d . . . . .
H14 H 0.0009 0.5671 -0.0235 0.056 Uiso 1 1 calc R U . . .
C15 C -0.0098(6) 0.6191(5) 0.0860(2) 0.0432(11) Uani 1 1 d . . . . .
H15 H -0.0030 0.7088 0.0774 0.052 Uiso 1 1 calc R U . . .
C16 C -0.0220(6) 0.5729(4) 0.1586(2) 0.0367(10) Uani 1 1 d . . . . .
H16 H -0.0205 0.6311 0.1998 0.044 Uiso 1 1 calc R U . . .
C17 C 0.3612(6) 0.1780(4) 0.2334(2) 0.0323(10) Uani 1 1 d . . . . .
C18 C 0.2888(5) 0.0270(4) 0.3208(2) 0.0307(9) Uani 1 1 d . . . . .
C19 C 0.2563(6) -0.0023(4) 0.3977(2) 0.0318(10) Uani 1 1 d . . . . .
C20 C 0.2623(6) 0.0941(4) 0.4529(2) 0.0343(10) Uani 1 1 d . . . . .
H20 H 0.2911 0.1799 0.4401 0.041 Uiso 1 1 calc R U . . .
C21 C 0.2264(6) 0.0636(5) 0.5256(2) 0.0394(11) Uani 1 1 d . . . . .
H21 H 0.2307 0.1287 0.5631 0.047 Uiso 1 1 calc R U . . .
C22 C 0.1834(6) -0.0627(5) 0.5449(2) 0.0415(11) Uani 1 1 d . . . . .
H22 H 0.1590 -0.0825 0.5955 0.050 Uiso 1 1 calc R U . . .
C23 C 0.1764(6) -0.1573(4) 0.4919(2) 0.0384(10) Uani 1 1 d . . . . .
H23 H 0.1452 -0.2423 0.5055 0.046 Uiso 1 1 calc R U . . .
C24 C 0.2150(6) -0.1298(4) 0.4170(2) 0.0334(9) Uani 1 1 d . . . . .
C25 C 0.2129(6) -0.2252(4) 0.3601(2) 0.0389(10) Uani 1 1 d . . . . .
H25 H 0.1896 -0.3122 0.3722 0.047 Uiso 1 1 calc R U . . .
C26 C 0.2441(6) -0.1918(4) 0.2888(2) 0.0353(9) Uani 1 1 d . . . . .
H26 H 0.2421 -0.2565 0.2511 0.042 Uiso 1 1 calc R U . . .
C27 C 0.4122(6) 0.3093(4) 0.2137(2) 0.0319(9) Uani 1 1 d . . . . .
C28 C 0.4402(6) 0.4021(4) 0.2701(2) 0.0381(10) Uani 1 1 d . . . . .
H28 H 0.4271 0.3802 0.3213 0.046 Uiso 1 1 calc R U . . .
C29 C 0.4870(6) 0.5253(4) 0.2513(3) 0.0458(12) Uani 1 1 d . . . . .
H29 H 0.5064 0.5882 0.2898 0.055 Uiso 1 1 calc R U . . .
C30 C 0.5060(6) 0.5587(5) 0.1767(3) 0.0470(12) Uani 1 1 d . . . . .
H30 H 0.5362 0.6444 0.1641 0.056 Uiso 1 1 calc R U . . .
C31 C 0.4809(6) 0.4667(4) 0.1206(3) 0.0421(11) Uani 1 1 d . . . . .
H31 H 0.4958 0.4890 0.0695 0.051 Uiso 1 1 calc R U . . .
C32 C 0.4345(6) 0.3433(4) 0.1386(2) 0.0387(10) Uani 1 1 d . . . . .
H32 H 0.4175 0.2806 0.0998 0.046 Uiso 1 1 calc R U . . .
B1 B -0.0611(8) 0.4515(5) 0.3806(3) 0.0373(12) Uani 1 1 d . . . . .
B2 B 0.2946(7) -0.0365(5) 0.1833(3) 0.0340(11) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.372(6) . ?
F2 B1 1.379(6) . ?
F3 B2 1.380(5) . ?
F4 B2 1.382(5) . ?
O1 C1 1.321(5) . ?
O1 B1 1.456(6) . ?
O2 C17 1.321(4) . ?
O2 B2 1.458(6) . ?
N1 C1 1.300(5) . ?
N1 C2 1.365(4) . ?
N2 C2 1.343(4) . ?
N2 C10 1.374(5) . ?
N2 B1 1.566(6) . ?
N3 C17 1.296(5) . ?
N3 C18 1.364(5) . ?
N4 C18 1.341(5) . ?
N4 C26 1.383(5) . ?
N4 B2 1.560(6) . ?
C1 C11 1.465(5) . ?
C2 C3 1.435(5) . ?
C3 C4 1.409(5) . ?
C3 C8 1.410(6) . ?
C4 C5 1.375(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.364(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.413(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(6) . ?
C9 C10 1.346(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.390(6) . ?
C11 C12 1.393(6) . ?
C12 C13 1.378(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C27 1.467(5) . ?
C18 C19 1.437(5) . ?
C19 C20 1.402(5) . ?
C19 C24 1.410(6) . ?
C20 C21 1.372(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.402(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.362(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.408(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.416(5) . ?
C25 C26 1.348(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.395(5) . ?
C27 C32 1.402(6) . ?
C28 C29 1.376(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.385(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.373(6) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

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 O1 B1 122.8(3) . . ?
C17 O2 B2 122.8(3) . . ?
C1 N1 C2 119.4(3) . . ?
C2 N2 C10 121.1(3) . . ?
C2 N2 B1 120.4(3) . . ?
C10 N2 B1 118.5(3) . . ?
C17 N3 C18 119.4(3) . . ?
C18 N4 C26 120.7(3) . . ?
C18 N4 B2 121.3(3) . . ?
C26 N4 B2 117.9(3) . . ?
N1 C1 O1 125.4(4) . . ?
N1 C1 C11 120.3(4) . . ?
O1 C1 C11 114.2(4) . . ?
N2 C2 N1 122.0(3) . . ?
N2 C2 C3 119.4(3) . . ?
N1 C2 C3 118.6(3) . . ?
C4 C3 C8 119.8(4) . . ?
C4 C3 C2 121.1(4) . . ?
C8 C3 C2 119.1(3) . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C3 C8 C7 119.1(4) . . ?
C3 C8 C9 118.5(4) . . ?
C7 C8 C9 122.4(4) . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 N2 122.3(4) . . ?
C9 C10 H10 118.9 . . ?
N2 C10 H10 118.9 . . ?
C16 C11 C12 119.0(4) . . ?
C16 C11 C1 120.8(4) . . ?
C12 C11 C1 120.2(4) . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.4(4) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N3 C17 O2 125.7(4) . . ?
N3 C17 C27 119.9(4) . . ?
O2 C17 C27 114.5(3) . . ?
N4 C18 N3 121.5(3) . . ?
N4 C18 C19 119.8(4) . . ?
N3 C18 C19 118.7(4) . . ?
C20 C19 C24 120.2(4) . . ?
C20 C19 C18 120.9(4) . . ?
C24 C19 C18 118.9(4) . . ?
C21 C20 C19 119.5(4) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 120.6(4) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.3(4) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 118.8(4) . . ?
C23 C24 C25 122.5(4) . . ?
C19 C24 C25 118.7(4) . . ?
C26 C25 C24 119.6(4) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 N4 122.2(4) . . ?
C25 C26 H26 118.9 . . ?
N4 C26 H26 118.9 . . ?
C28 C27 C32 119.1(4) . . ?
C28 C27 C17 120.1(4) . . ?
C32 C27 C17 120.8(4) . . ?
C29 C28 C27 119.9(4) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.7(5) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 119.7(5) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C32 C31 C30 120.2(5) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C27 120.4(4) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?
F1 B1 F2 110.2(4) . . ?
F1 B1 O1 110.0(4) . . ?
F2 B1 O1 109.8(4) . . ?
F1 B1 N2 109.1(4) . . ?
F2 B1 N2 108.6(4) . . ?
O1 B1 N2 109.0(3) . . ?
F3 B2 F4 109.7(4) . . ?
F3 B2 O2 109.8(4) . . ?
F4 B2 O2 110.1(4) . . ?
F3 B2 N4 109.6(3) . . ?
F4 B2 N4 109.0(3) . . ?
O2 B2 N4 108.5(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
C2 N1 C1 O1 3.1(6) . . . . ?
C2 N1 C1 C11 -174.0(3) . . . . ?
B1 O1 C1 N1 4.2(6) . . . . ?
B1 O1 C1 C11 -178.6(4) . . . . ?
C10 N2 C2 N1 176.9(3) . . . . ?
B1 N2 C2 N1 -5.4(5) . . . . ?
C10 N2 C2 C3 -1.7(5) . . . . ?
B1 N2 C2 C3 175.9(4) . . . . ?
C1 N1 C2 N2 -2.1(5) . . . . ?
C1 N1 C2 C3 176.6(4) . . . . ?
N2 C2 C3 C4 -177.7(4) . . . . ?
N1 C2 C3 C4 3.6(5) . . . . ?
N2 C2 C3 C8 1.6(5) . . . . ?
N1 C2 C3 C8 -177.1(3) . . . . ?
C8 C3 C4 C5 -1.2(6) . . . . ?
C2 C3 C4 C5 178.1(4) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C7 1.0(7) . . . . ?
C5 C6 C7 C8 -1.3(6) . . . . ?
C4 C3 C8 C7 0.9(6) . . . . ?
C2 C3 C8 C7 -178.4(4) . . . . ?
C4 C3 C8 C9 179.3(4) . . . . ?
C2 C3 C8 C9 0.0(5) . . . . ?
C6 C7 C8 C3 0.4(6) . . . . ?
C6 C7 C8 C9 -178.0(4) . . . . ?
C3 C8 C9 C10 -1.5(6) . . . . ?
C7 C8 C9 C10 176.9(4) . . . . ?
C8 C9 C10 N2 1.5(6) . . . . ?
C2 N2 C10 C9 0.2(6) . . . . ?
B1 N2 C10 C9 -177.5(4) . . . . ?
N1 C1 C11 C16 171.1(4) . . . . ?
O1 C1 C11 C16 -6.3(5) . . . . ?
N1 C1 C11 C12 -7.4(6) . . . . ?
O1 C1 C11 C12 175.2(4) . . . . ?
C16 C11 C12 C13 -0.6(6) . . . . ?
C1 C11 C12 C13 177.8(4) . . . . ?
C11 C12 C13 C14 -0.8(7) . . . . ?
C12 C13 C14 C15 1.1(7) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C14 C15 C16 C11 -1.5(6) . . . . ?
C12 C11 C16 C15 1.8(6) . . . . ?
C1 C11 C16 C15 -176.7(4) . . . . ?
C18 N3 C17 O2 1.7(6) . . . . ?
C18 N3 C17 C27 -177.8(4) . . . . ?
B2 O2 C17 N3 4.0(6) . . . . ?
B2 O2 C17 C27 -176.5(4) . . . . ?
C26 N4 C18 N3 177.5(3) . . . . ?
B2 N4 C18 N3 -6.1(6) . . . . ?
C26 N4 C18 C19 -2.3(6) . . . . ?
B2 N4 C18 C19 174.1(4) . . . . ?
C17 N3 C18 N4 -0.3(6) . . . . ?
C17 N3 C18 C19 179.4(3) . . . . ?
N4 C18 C19 C20 -178.8(4) . . . . ?
N3 C18 C19 C20 1.5(6) . . . . ?
N4 C18 C19 C24 0.2(6) . . . . ?
N3 C18 C19 C24 -179.5(4) . . . . ?
C24 C19 C20 C21 -0.5(6) . . . . ?
C18 C19 C20 C21 178.5(4) . . . . ?
C19 C20 C21 C22 -0.1(6) . . . . ?
C20 C21 C22 C23 -0.1(7) . . . . ?
C21 C22 C23 C24 1.0(6) . . . . ?
C22 C23 C24 C19 -1.6(6) . . . . ?
C22 C23 C24 C25 178.8(4) . . . . ?
C20 C19 C24 C23 1.4(6) . . . . ?
C18 C19 C24 C23 -177.6(4) . . . . ?
C20 C19 C24 C25 -179.0(4) . . . . ?
C18 C19 C24 C25 1.9(6) . . . . ?
C23 C24 C25 C26 177.4(4) . . . . ?
C19 C24 C25 C26 -2.1(6) . . . . ?
C24 C25 C26 N4 0.1(6) . . . . ?
C18 N4 C26 C25 2.2(6) . . . . ?
B2 N4 C26 C25 -174.4(4) . . . . ?
N3 C17 C27 C28 4.6(6) . . . . ?
O2 C17 C27 C28 -174.9(4) . . . . ?
N3 C17 C27 C32 -175.8(4) . . . . ?
O2 C17 C27 C32 4.7(5) . . . . ?
C32 C27 C28 C29 0.8(6) . . . . ?
C17 C27 C28 C29 -179.6(4) . . . . ?
C27 C28 C29 C30 0.2(7) . . . . ?
C28 C29 C30 C31 -1.1(7) . . . . ?
C29 C30 C31 C32 1.0(7) . . . . ?
C30 C31 C32 C27 0.0(7) . . . . ?
C28 C27 C32 C31 -0.9(6) . . . . ?
C17 C27 C32 C31 179.5(4) . . . . ?
C1 O1 B1 F1 -129.9(4) . . . . ?
C1 O1 B1 F2 108.6(4) . . . . ?
C1 O1 B1 N2 -10.2(6) . . . . ?
C2 N2 B1 F1 131.0(4) . . . . ?
C10 N2 B1 F1 -51.3(5) . . . . ?
C2 N2 B1 F2 -108.8(4) . . . . ?
C10 N2 B1 F2 68.9(5) . . . . ?
C2 N2 B1 O1 10.8(6) . . . . ?
C10 N2 B1 O1 -171.5(3) . . . . ?
C17 O2 B2 F3 -128.9(4) . . . . ?
C17 O2 B2 F4 110.2(4) . . . . ?
C17 O2 B2 N4 -9.0(5) . . . . ?
C18 N4 B2 F3 130.0(4) . . . . ?
C26 N4 B2 F3 -53.4(5) . . . . ?
C18 N4 B2 F4 -109.8(4) . . . . ?
C26 N4 B2 F4 66.7(5) . . . . ?
C18 N4 B2 O2 10.1(5) . . . . ?
C26 N4 B2 O2 -173.4(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





_publcif_funding_html            
;
;

####################################################################### 
# 
# 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_3-T@py
_database_code_depnum_ccdc_archive 'CCDC 1881150'
loop_
_audit_author_name
_audit_author_address
'Kenta Goto'
;Kyushu University
Japan
;
_audit_update_record             
;
2018-11-26 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H7 B F2 N2 O S'
_chemical_formula_moiety         'C10 H7 B F2 N2 O S'
_chemical_formula_weight         252.04
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.3383(3)
_cell_length_b                   11.6331(5)
_cell_length_c                   12.4095(5)
_cell_angle_alpha                83.136(6)
_cell_angle_beta                 79.631(6)
_cell_angle_gamma                83.755(6)
_cell_volume                     1030.46(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10291
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      68.21
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512.00
_exptl_absorpt_coefficient_mu    2.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_T_max  0.746

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            12208
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_theta_max         68.211
_diffrn_reflns_theta_min         3.640
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3703
_reflns_number_gt                2899
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1323
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3703
_refine_ls_number_parameters     307
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
S1 S 0.35237(10) 0.39425(7) -0.36961(6) 0.0311(2) Uani 1 1 d . . . . .
S2 S 0.18452(10) 0.10392(7) 0.07796(6) 0.0325(2) Uani 1 1 d . . . . .
F1 F 0.8275(2) 0.29729(13) 0.02028(13) 0.0323(4) Uani 1 1 d . . . . .
F2 F 0.6932(2) 0.12807(13) 0.05999(13) 0.0308(4) Uani 1 1 d . . . . .
F3 F -0.2854(2) 0.23132(14) 0.54425(13) 0.0346(4) Uani 1 1 d . . . . .
F4 F -0.1085(2) 0.38345(13) 0.52072(14) 0.0403(5) Uani 1 1 d . . . . .
O1 O 0.5679(2) 0.27428(15) -0.05620(15) 0.0258(5) Uani 1 1 d . . . . .
O2 O -0.0194(3) 0.23307(16) 0.40965(16) 0.0283(5) Uani 1 1 d . . . . .
N1 N 0.3375(3) 0.40799(18) 0.02438(19) 0.0223(5) Uani 1 1 d . . . . .
N2 N 0.5326(3) 0.29689(18) 0.14155(19) 0.0225(5) Uani 1 1 d . . . . .
N3 N 0.1882(3) 0.08480(19) 0.47311(19) 0.0253(5) Uani 1 1 d . . . . .
N4 N 0.0086(3) 0.20157(18) 0.60662(18) 0.0216(5) Uani 1 1 d . . . . .
C1 C 0.4240(4) 0.3544(2) -0.0577(2) 0.0222(6) Uani 1 1 d . . . . .
C2 C 0.3900(4) 0.3783(2) 0.1269(2) 0.0240(6) Uani 1 1 d . . . . .
C3 C 0.2910(4) 0.4317(2) 0.2165(2) 0.0243(6) Uani 1 1 d . . . . .
H7 H 0.193256 0.490381 0.206205 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3334(4) 0.4001(2) 0.3197(2) 0.0281(7) Uani 1 1 d . . . . .
H5 H 0.266521 0.437246 0.380907 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4765(4) 0.3124(2) 0.3340(2) 0.0291(7) Uani 1 1 d . . . . .
H13 H 0.505668 0.287107 0.405091 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5722(4) 0.2646(2) 0.2435(2) 0.0268(7) Uani 1 1 d . . . . .
H17 H 0.670786 0.206051 0.252363 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3646(4) 0.3821(2) -0.1642(2) 0.0229(6) Uani 1 1 d . . . . .
C8 C 0.4480(4) 0.3333(2) -0.2591(2) 0.0214(6) Uani 1 1 d . . . . .
H10 H 0.546708 0.273130 -0.262170 0.026 Uiso 1 1 calc R U . . .
C9 C 0.1949(4) 0.4839(2) -0.2924(2) 0.0279(7) Uani 1 1 d . . . . .
H20 H 0.103994 0.537214 -0.321348 0.033 Uiso 1 1 calc R U . . .
C10 C 0.2151(4) 0.4699(2) -0.1836(2) 0.0224(6) Uani 1 1 d . . . . .
H16 H 0.140565 0.512373 -0.128153 0.027 Uiso 1 1 calc R U . . .
C11 C 0.1078(4) 0.1436(2) 0.3971(2) 0.0231(6) Uani 1 1 d . . . . .
C12 C 0.1434(4) 0.1151(2) 0.5789(2) 0.0248(6) Uani 1 1 d . . . . .
C13 C 0.2403(4) 0.0579(2) 0.6594(2) 0.0292(7) Uani 1 1 d . . . . .
H14 H 0.336591 -0.001361 0.640667 0.035 Uiso 1 1 calc R U . . .
C14 C 0.1978(4) 0.0866(2) 0.7652(2) 0.0302(7) Uani 1 1 d . . . . .
H15 H 0.261898 0.045769 0.820186 0.036 Uiso 1 1 calc R U . . .
C15 C 0.0604(4) 0.1758(2) 0.7923(2) 0.0286(7) Uani 1 1 d . . . . .
H9 H 0.030869 0.197770 0.865192 0.034 Uiso 1 1 calc R U . . .
C16 C -0.0303(4) 0.2305(2) 0.7113(2) 0.0258(6) Uani 1 1 d . . . . .
H12 H -0.124424 0.291392 0.728981 0.031 Uiso 1 1 calc R U . . .
C17 C 0.1613(4) 0.1121(2) 0.2843(2) 0.0240(6) Uani 1 1 d . . . . .
C18 C 0.0953(4) 0.1698(2) 0.1938(2) 0.0249(6) Uani 1 1 d . . . . .
H19 H 0.010718 0.237767 0.195701 0.030 Uiso 1 1 calc R U . . .
C19 C 0.3115(4) -0.0004(2) 0.1474(3) 0.0306(7) Uani 1 1 d . . . . .
H18 H 0.390316 -0.060968 0.113566 0.037 Uiso 1 1 calc R U . . .
C20 C 0.2884(3) 0.0119(2) 0.2569(2) 0.0225(6) Uani 1 1 d . . . . .
H22 H 0.347929 -0.038651 0.308543 0.027 Uiso 1 1 calc R U . . .
B1 B 0.6609(4) 0.2466(3) 0.0387(3) 0.0263(8) Uani 1 1 d . . . . .
B2 B -0.1068(5) 0.2654(3) 0.5190(3) 0.0271(8) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
S1 C8 1.697(3) . ?
S1 C9 1.709(3) . ?
S2 C19 1.696(3) . ?
S2 C18 1.703(3) . ?
F1 B1 1.385(3) . ?
F2 B1 1.375(3) . ?
F3 B2 1.382(3) . ?
F4 B2 1.374(3) . ?
O1 C1 1.331(3) . ?
O1 B1 1.452(4) . ?
O2 C11 1.325(3) . ?
O2 B2 1.467(4) . ?
N1 C1 1.289(3) . ?
N1 C2 1.389(3) . ?
N2 C6 1.350(3) . ?
N2 C2 1.355(3) . ?
N2 B1 1.576(4) . ?
N3 C11 1.290(3) . ?
N3 C12 1.373(4) . ?
N4 C16 1.354(3) . ?
N4 C12 1.361(3) . ?
N4 B2 1.566(4) . ?
C1 C7 1.454(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.371(4) . ?
C3 H7 0.9500 . ?
C4 C5 1.402(4) . ?
C4 H5 0.9500 . ?
C5 C6 1.358(4) . ?
C5 H13 0.9500 . ?
C6 H17 0.9500 . ?
C7 C8 1.382(4) . ?
C7 C10 1.449(4) . ?
C8 H10 0.9500 . ?
C9 C10 1.373(4) . ?
C9 H20 0.9500 . ?
C10 H16 0.9500 . ?
C11 C17 1.463(4) . ?
C12 C13 1.393(4) . ?
C13 C14 1.366(4) . ?
C13 H14 0.9500 . ?
C14 C15 1.393(4) . ?
C14 H15 0.9500 . ?
C15 C16 1.362(4) . ?
C15 H9 0.9500 . ?
C16 H12 0.9500 . ?
C17 C18 1.375(4) . ?
C17 C20 1.444(3) . ?
C18 H19 0.9500 . ?
C19 C20 1.362(4) . ?
C19 H18 0.9500 . ?
C20 H22 0.9500 . ?

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
C8 S1 C9 92.79(13) . . ?
C19 S2 C18 92.53(14) . . ?
C1 O1 B1 122.2(2) . . ?
C11 O2 B2 121.7(2) . . ?
C1 N1 C2 118.9(2) . . ?
C6 N2 C2 120.0(3) . . ?
C6 N2 B1 120.0(2) . . ?
C2 N2 B1 119.9(2) . . ?
C11 N3 C12 119.3(2) . . ?
C16 N4 C12 120.0(2) . . ?
C16 N4 B2 119.5(2) . . ?
C12 N4 B2 120.4(2) . . ?
N1 C1 O1 126.3(3) . . ?
N1 C1 C7 119.0(2) . . ?
O1 C1 C7 114.7(2) . . ?
N2 C2 C3 119.6(3) . . ?
N2 C2 N1 121.5(3) . . ?
C3 C2 N1 118.9(2) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H7 119.8 . . ?
C2 C3 H7 119.8 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H5 120.3 . . ?
C5 C4 H5 120.3 . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 H13 120.9 . . ?
C4 C5 H13 120.9 . . ?
N2 C6 C5 122.6(3) . . ?
N2 C6 H17 118.7 . . ?
C5 C6 H17 118.7 . . ?
C8 C7 C10 112.1(3) . . ?
C8 C7 C1 124.8(2) . . ?
C10 C7 C1 123.0(3) . . ?
C7 C8 S1 111.6(2) . . ?
C7 C8 H10 124.2 . . ?
S1 C8 H10 124.2 . . ?
C10 C9 S1 112.2(2) . . ?
C10 C9 H20 123.9 . . ?
S1 C9 H20 123.9 . . ?
C9 C10 C7 111.2(3) . . ?
C9 C10 H16 124.4 . . ?
C7 C10 H16 124.4 . . ?
N3 C11 O2 126.5(3) . . ?
N3 C11 C17 118.5(3) . . ?
O2 C11 C17 115.0(2) . . ?
N4 C12 N3 121.5(2) . . ?
N4 C12 C13 119.0(3) . . ?
N3 C12 C13 119.5(3) . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H14 119.8 . . ?
C12 C13 H14 119.8 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H15 120.0 . . ?
C15 C14 H15 120.0 . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 H9 121.0 . . ?
C14 C15 H9 121.0 . . ?
N4 C16 C15 122.5(3) . . ?
N4 C16 H12 118.7 . . ?
C15 C16 H12 118.7 . . ?
C18 C17 C20 112.3(3) . . ?
C18 C17 C11 125.3(3) . . ?
C20 C17 C11 122.4(3) . . ?
C17 C18 S2 111.3(2) . . ?
C17 C18 H19 124.4 . . ?
S2 C18 H19 124.4 . . ?
C20 C19 S2 112.8(2) . . ?
C20 C19 H18 123.6 . . ?
S2 C19 H18 123.6 . . ?
C19 C20 C17 111.1(3) . . ?
C19 C20 H22 124.5 . . ?
C17 C20 H22 124.5 . . ?
F2 B1 F1 109.9(2) . . ?
F2 B1 O1 110.0(2) . . ?
F1 B1 O1 110.3(3) . . ?
F2 B1 N2 109.4(2) . . ?
F1 B1 N2 108.3(2) . . ?
O1 B1 N2 108.8(2) . . ?
F4 B2 F3 110.7(2) . . ?
F4 B2 O2 109.6(2) . . ?
F3 B2 O2 109.7(3) . . ?
F4 B2 N4 109.1(2) . . ?
F3 B2 N4 108.7(2) . . ?
O2 B2 N4 109.0(2) . . ?

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 N1 C1 O1 -3.0(4) . . . . ?
C2 N1 C1 C7 177.6(2) . . . . ?
B1 O1 C1 N1 -7.5(4) . . . . ?
B1 O1 C1 C7 171.9(2) . . . . ?
C6 N2 C2 C3 2.9(4) . . . . ?
B1 N2 C2 C3 -172.8(2) . . . . ?
C6 N2 C2 N1 -175.6(2) . . . . ?
B1 N2 C2 N1 8.7(4) . . . . ?
C1 N1 C2 N2 1.8(4) . . . . ?
C1 N1 C2 C3 -176.8(2) . . . . ?
N2 C2 C3 C4 -1.8(4) . . . . ?
N1 C2 C3 C4 176.7(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 2.2(4) . . . . ?
C2 N2 C6 C5 -1.5(4) . . . . ?
B1 N2 C6 C5 174.2(3) . . . . ?
C4 C5 C6 N2 -1.1(4) . . . . ?
N1 C1 C7 C8 178.3(2) . . . . ?
O1 C1 C7 C8 -1.2(4) . . . . ?
N1 C1 C7 C10 1.7(4) . . . . ?
O1 C1 C7 C10 -177.7(2) . . . . ?
C10 C7 C8 S1 1.5(3) . . . . ?
C1 C7 C8 S1 -175.4(2) . . . . ?
C9 S1 C8 C7 -1.4(2) . . . . ?
C8 S1 C9 C10 0.9(2) . . . . ?
S1 C9 C10 C7 -0.3(3) . . . . ?
C8 C7 C10 C9 -0.8(3) . . . . ?
C1 C7 C10 C9 176.2(2) . . . . ?
C12 N3 C11 O2 -0.5(4) . . . . ?
C12 N3 C11 C17 178.3(2) . . . . ?
B2 O2 C11 N3 -9.8(4) . . . . ?
B2 O2 C11 C17 171.4(2) . . . . ?
C16 N4 C12 N3 -179.0(2) . . . . ?
B2 N4 C12 N3 3.0(4) . . . . ?
C16 N4 C12 C13 -0.4(4) . . . . ?
B2 N4 C12 C13 -178.4(2) . . . . ?
C11 N3 C12 N4 3.7(4) . . . . ?
C11 N3 C12 C13 -174.9(3) . . . . ?
N4 C12 C13 C14 1.4(4) . . . . ?
N3 C12 C13 C14 -179.9(2) . . . . ?
C12 C13 C14 C15 -1.9(4) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C12 N4 C16 C15 -0.3(4) . . . . ?
B2 N4 C16 C15 177.7(3) . . . . ?
C14 C15 C16 N4 -0.1(4) . . . . ?
N3 C11 C17 C18 -176.6(3) . . . . ?
O2 C11 C17 C18 2.3(4) . . . . ?
N3 C11 C17 C20 5.4(4) . . . . ?
O2 C11 C17 C20 -175.6(2) . . . . ?
C20 C17 C18 S2 0.2(3) . . . . ?
C11 C17 C18 S2 -177.9(2) . . . . ?
C19 S2 C18 C17 -0.3(2) . . . . ?
C18 S2 C19 C20 0.4(2) . . . . ?
S2 C19 C20 C17 -0.3(3) . . . . ?
C18 C17 C20 C19 0.1(3) . . . . ?
C11 C17 C20 C19 178.3(2) . . . . ?
C1 O1 B1 F2 135.7(2) . . . . ?
C1 O1 B1 F1 -102.9(3) . . . . ?
C1 O1 B1 N2 15.9(3) . . . . ?
C6 N2 B1 F2 47.6(3) . . . . ?
C2 N2 B1 F2 -136.7(2) . . . . ?
C6 N2 B1 F1 -72.1(3) . . . . ?
C2 N2 B1 F1 103.5(3) . . . . ?
C6 N2 B1 O1 167.9(2) . . . . ?
C2 N2 B1 O1 -16.5(3) . . . . ?
C11 O2 B2 F4 133.6(2) . . . . ?
C11 O2 B2 F3 -104.6(3) . . . . ?
C11 O2 B2 N4 14.3(4) . . . . ?
C16 N4 B2 F4 51.1(3) . . . . ?
C12 N4 B2 F4 -130.8(3) . . . . ?
C16 N4 B2 F3 -69.7(3) . . . . ?
C12 N4 B2 F3 108.3(3) . . . . ?
C16 N4 B2 O2 170.8(2) . . . . ?
C12 N4 B2 O2 -11.2(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





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

data_2-T@Py
_database_code_depnum_ccdc_archive 'CCDC 1881152'
loop_
_audit_author_name
_audit_author_address
'Kenta Goto'
;Kyushu University
Japan
;
_audit_update_record             
;
2018-11-26 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H7 B F2 N2 O S'
_chemical_formula_moiety         'C10 H7 B F2 N2 O S'
_chemical_formula_weight         252.04
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_space_group_IT_number           33
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 1/2-X,1/2+Y,1/2+Z
4 1/2+X,1/2-Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.855(5)
_cell_length_b                   13.112(4)
_cell_length_c                   4.9675(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1032.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4288
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      31.03
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512.00
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.997

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_reflns_number            5597
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.003
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2246
_reflns_number_gt                2055
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_max     0.881
_reflns_Friedel_fraction_full    0.925

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0724
_refine_ls_number_restraints     71
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2246
_refine_ls_number_parameters     200
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0237P)²+0.3063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
S1 S -0.00919(7) 0.74259(8) 1.1121(3) 0.0302(3) Uani 0.850(4) 1 d D U P A 1
C1 C 0.0871(8) 0.7120(9) 0.986(4) 0.0240(19) Uani 0.850(4) 1 d D U P A 1
C2 C 0.1171(6) 0.6241(6) 1.093(2) 0.037(2) Uani 0.850(4) 1 d D U P A 1
H2 H 0.1699 0.5955 1.0432 0.044 Uiso 0.850(4) 1 calc R U P A 1
C3 C 0.0634(6) 0.5791(8) 1.283(2) 0.036(2) Uani 0.850(4) 1 d D U P A 1
H3 H 0.0745 0.5169 1.3746 0.043 Uiso 0.850(4) 1 calc R U P A 1
C4 C -0.0074(4) 0.6376(5) 1.3199(16) 0.0267(13) Uani 0.850(4) 1 d D U P A 1
H4 H -0.0507 0.6219 1.4457 0.032 Uiso 0.850(4) 1 calc R U P A 1
S1A S 0.1316(8) 0.5975(9) 1.072(3) 0.032(2) Uani 0.150(4) 1 d D U P A 2
C1A C 0.093(5) 0.711(6) 0.96(2) 0.031(13) Uani 0.150(4) 1 d D U P A 2
C2A C 0.021(2) 0.727(3) 1.091(9) 0.071(14) Uani 0.150(4) 1 d D U P A 2
H2A H -0.0087 0.7899 1.0672 0.085 Uiso 0.150(4) 1 calc R U P A 2
C3A C -0.011(3) 0.652(4) 1.261(11) 0.043(11) Uani 0.150(4) 1 d D U P A 2
H3A H -0.0665 0.6505 1.3364 0.051 Uiso 0.150(4) 1 calc R U P A 2
C4A C 0.051(3) 0.581(4) 1.299(12) 0.030(9) Uani 0.150(4) 1 d D U P A 2
H4A H 0.0498 0.5296 1.4329 0.036 Uiso 0.150(4) 1 calc R U P A 2
F1 F 0.29525(11) 0.74572(12) 0.3379(4) 0.0342(5) Uani 1 1 d . . . . .
F2 F 0.31981(10) 0.84855(14) 0.6943(4) 0.0378(5) Uani 1 1 d . . . . .
O1 O 0.20173(12) 0.74122(15) 0.6974(5) 0.0317(5) Uani 1 1 d . . . . .
N1 N 0.09167(14) 0.85942(17) 0.7062(5) 0.0276(6) Uani 1 1 d . . . . .
N2 N 0.20546(14) 0.89164(17) 0.4044(5) 0.0247(6) Uani 1 1 d . . . . .
C5 C 0.12837(18) 0.7764(2) 0.7845(6) 0.0260(7) Uani 1 1 d . . . . .
C6 C 0.12891(17) 0.9170(2) 0.5074(6) 0.0260(7) Uani 1 1 d . . . . .
C7 C 0.08746(19) 1.0029(2) 0.4051(7) 0.0337(8) Uani 1 1 d . . . . .
H7 H 0.0342 1.0223 0.4762 0.040 Uiso 1 1 calc R U . . .
C8 C 0.12337(18) 1.0591(2) 0.2029(8) 0.0345(7) Uani 1 1 d . . . . .
H8 H 0.0955 1.1179 0.1354 0.041 Uiso 1 1 calc R U . . .
C9 C 0.20093(18) 1.0295(2) 0.0966(8) 0.0321(7) Uani 1 1 d . . . . .
H9 H 0.2260 1.0671 -0.0460 0.038 Uiso 1 1 calc R U . . .
C10 C 0.24031(17) 0.9462(2) 0.2000(7) 0.0288(7) Uani 1 1 d . . . . .
H10 H 0.2932 0.9257 0.1280 0.035 Uiso 1 1 calc R U . . .
B1 B 0.2586(2) 0.8034(2) 0.5354(7) 0.0276(8) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
S1 C1 1.698(8) . ?
S1 C4 1.721(5) . ?
C1 C2 1.354(10) . ?
C1 C5 1.465(6) . ?
C2 C3 1.403(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(6) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
S1A C1A 1.70(3) . ?
S1A C4A 1.72(3) . ?
C1A C2A 1.33(3) . ?
C1A C5 1.35(3) . ?
C2A C3A 1.39(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.37(2) . ?
C3A H3A 0.9500 . ?
C4A H4A 0.9500 . ?
F1 B1 1.368(4) . ?
F2 B1 1.384(4) . ?
O1 C5 1.324(3) . ?
O1 B1 1.458(4) . ?
N1 C5 1.295(4) . ?
N1 C6 1.376(4) . ?
N2 C6 1.358(3) . ?
N2 C10 1.360(4) . ?
N2 B1 1.572(4) . ?
C6 C7 1.400(4) . ?
C7 C8 1.370(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.359(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

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 S1 C4 91.0(3) . . ?
C2 C1 C5 127.0(7) . . ?
C2 C1 S1 111.9(5) . . ?
C5 C1 S1 121.2(5) . . ?
C1 C2 C3 114.1(6) . . ?
C1 C2 H2 122.9 . . ?
C3 C2 H2 122.9 . . ?
C4 C3 C2 110.5(6) . . ?
C4 C3 H3 124.7 . . ?
C2 C3 H3 124.7 . . ?
C3 C4 S1 112.4(5) . . ?
C3 C4 H4 123.8 . . ?
S1 C4 H4 123.8 . . ?
C1A S1A C4A 93.1(17) . . ?
C2A C1A C5 124(3) . . ?
C2A C1A S1A 107.2(19) . . ?
C5 C1A S1A 128(3) . . ?
C1A C2A C3A 119(3) . . ?
C1A C2A H2A 120.3 . . ?
C3A C2A H2A 120.3 . . ?
C4A C3A C2A 107(3) . . ?
C4A C3A H3A 126.3 . . ?
C2A C3A H3A 126.3 . . ?
C3A C4A S1A 111(3) . . ?
C3A C4A H4A 124.4 . . ?
S1A C4A H4A 124.4 . . ?
C5 O1 B1 122.0(2) . . ?
C5 N1 C6 119.0(2) . . ?
C6 N2 C10 121.0(2) . . ?
C6 N2 B1 120.2(2) . . ?
C10 N2 B1 118.6(2) . . ?
N1 C5 O1 126.1(3) . . ?
N1 C5 C1A 123.1(18) . . ?
O1 C5 C1A 110.7(17) . . ?
N1 C5 C1 119.3(4) . . ?
O1 C5 C1 114.6(4) . . ?
N2 C6 N1 121.3(3) . . ?
N2 C6 C7 118.7(3) . . ?
N1 C6 C7 120.0(3) . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 N2 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
N2 C10 H10 119.4 . . ?
F1 B1 F2 110.4(2) . . ?
F1 B1 O1 110.4(2) . . ?
F2 B1 O1 111.0(3) . . ?
F1 B1 N2 109.7(3) . . ?
F2 B1 N2 107.3(2) . . ?
O1 B1 N2 108.0(2) . . ?

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
C4 S1 C1 C2 1.9(15) . . . . ?
C4 S1 C1 C5 -178.7(15) . . . . ?
C5 C1 C2 C3 179.8(17) . . . . ?
S1 C1 C2 C3 -1(2) . . . . ?
C1 C2 C3 C4 -1.2(19) . . . . ?
C2 C3 C4 S1 2.6(14) . . . . ?
C1 S1 C4 C3 -2.6(12) . . . . ?
C4A S1A C1A C2A -3(9) . . . . ?
C4A S1A C1A C5 175(12) . . . . ?
C5 C1A C2A C3A 177(9) . . . . ?
S1A C1A C2A C3A -5(12) . . . . ?
C1A C2A C3A C4A 12(11) . . . . ?
C2A C3A C4A S1A -13(7) . . . . ?
C1A S1A C4A C3A 10(7) . . . . ?
C6 N1 C5 O1 2.4(5) . . . . ?
C6 N1 C5 C1A -174(8) . . . . ?
C6 N1 C5 C1 -176.9(11) . . . . ?
B1 O1 C5 N1 12.1(5) . . . . ?
B1 O1 C5 C1A -171(7) . . . . ?
B1 O1 C5 C1 -168.6(10) . . . . ?
C2A C1A C5 N1 -5(16) . . . . ?
S1A C1A C5 N1 177(7) . . . . ?
C2A C1A C5 O1 177(10) . . . . ?
S1A C1A C5 O1 0(14) . . . . ?
C2 C1 C5 N1 -178.8(15) . . . . ?
S1 C1 C5 N1 2(2) . . . . ?
C2 C1 C5 O1 2(2) . . . . ?
S1 C1 C5 O1 -177.6(11) . . . . ?
C10 N2 C6 N1 177.1(3) . . . . ?
B1 N2 C6 N1 -7.6(4) . . . . ?
C10 N2 C6 C7 -2.2(4) . . . . ?
B1 N2 C6 C7 173.1(3) . . . . ?
C5 N1 C6 N2 -4.1(4) . . . . ?
C5 N1 C6 C7 175.2(3) . . . . ?
N2 C6 C7 C8 0.8(4) . . . . ?
N1 C6 C7 C8 -178.5(3) . . . . ?
C6 C7 C8 C9 0.9(5) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C8 C9 C10 N2 -0.1(5) . . . . ?
C6 N2 C10 C9 1.9(4) . . . . ?
B1 N2 C10 C9 -173.5(3) . . . . ?
C5 O1 B1 F1 -140.7(3) . . . . ?
C5 O1 B1 F2 96.6(3) . . . . ?
C5 O1 B1 N2 -20.7(4) . . . . ?
C6 N2 B1 F1 139.1(3) . . . . ?
C10 N2 B1 F1 -45.5(3) . . . . ?
C6 N2 B1 F2 -101.0(3) . . . . ?
C10 N2 B1 F2 74.4(3) . . . . ?
C6 N2 B1 O1 18.7(4) . . . . ?
C10 N2 B1 O1 -166.0(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





_publcif_funding_html            
;
;
####################################################################### 
# 
# 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-Np@py
_database_code_depnum_ccdc_archive 'CCDC 1881146'
loop_
_audit_author_name
_audit_author_address
'Kenta Goto'
;Kyushu University
Japan
;
_audit_update_record             
;
2018-11-26 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;
_publcif_datablock.id            {a987e7c5-a911-46f5-aaf9-efe821c2e691}

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H11 B F2 N2 O'
_chemical_formula_moiety         'C16 H11 B F2 N2 O'
_chemical_formula_weight         296.08
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.5092(4)
_cell_length_b                   7.9819(4)
_cell_length_c                   11.4185(5)
_cell_angle_alpha                100.717(7)
_cell_angle_beta                 98.301(7)
_cell_angle_gamma                97.041(7)
_cell_volume                     657.51(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6715
_cell_measurement_theta_min      4.00
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304.00
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_T_max  0.972

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            7844
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_theta_max         68.229
_diffrn_reflns_theta_min         3.999
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2364
_reflns_number_gt                1738
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1417
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2364
_refine_ls_number_parameters     199
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0870P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F2 F 0.16043(19) 0.17556(16) 0.38827(11) 0.0414(4) Uani 1 1 d . . . . .
F18 F 0.44669(18) 0.31106(16) 0.39568(11) 0.0391(4) Uani 1 1 d . . . . .
O19 O 0.2775(2) 0.16624(19) 0.20980(13) 0.0345(4) Uani 1 1 d . . . . .
N1 N 0.1777(2) 0.3644(2) 0.09918(15) 0.0271(5) Uani 1 1 d . . . . .
N20 N 0.1968(2) 0.4376(2) 0.31363(15) 0.0284(5) Uani 1 1 d . . . . .
C2 C 0.2400(3) 0.2226(3) 0.10887(19) 0.0260(5) Uani 1 1 d . . . . .
C3 C 0.1543(3) 0.4745(3) 0.20288(19) 0.0273(5) Uani 1 1 d . . . . .
C4 C 0.3116(3) 0.1534(3) -0.10687(19) 0.0272(5) Uani 1 1 d . . . . .
C5 C 0.3225(3) 0.0217(3) -0.20847(19) 0.0276(5) Uani 1 1 d . . . . .
C6 C 0.0827(3) 0.6248(3) 0.1916(2) 0.0288(5) Uani 1 1 d . . . . .
H6 H 0.0474 0.6483 0.1137 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2417(3) -0.0725(3) 0.0034(2) 0.0302(6) Uani 1 1 d . . . . .
H7 H 0.2187 -0.1060 0.0761 0.036 Uiso 1 1 calc R U . . .
C8 C 0.2880(3) -0.1538(3) -0.2007(2) 0.0327(6) Uani 1 1 d . . . . .
H8 H 0.2909 -0.2408 -0.2694 0.039 Uiso 1 1 calc R U . . .
C9 C 0.0631(3) 0.7390(3) 0.2930(2) 0.0330(6) Uani 1 1 d . . . . .
H9 H 0.0180 0.8434 0.2858 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1762(3) 0.5507(3) 0.4145(2) 0.0336(6) Uani 1 1 d . . . . .
H10 H 0.2086 0.5244 0.4918 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4103(3) 0.2389(3) -0.3200(2) 0.0331(6) Uani 1 1 d . . . . .
H11 H 0.4418 0.2691 -0.3919 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1100(3) 0.7007(3) 0.4066(2) 0.0360(6) Uani 1 1 d . . . . .
H12 H 0.0961 0.7779 0.4776 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3719(3) 0.0708(3) -0.3140(2) 0.0336(6) Uani 1 1 d . . . . .
H13 H 0.3781 -0.0161 -0.3818 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2510(3) -0.2005(3) -0.0976(2) 0.0315(6) Uani 1 1 d . . . . .
H14 H 0.2315 -0.3190 -0.0934 0.038 Uiso 1 1 calc R U . . .
C15 C 0.3567(3) 0.3281(3) -0.1162(2) 0.0284(5) Uani 1 1 d . . . . .
H15 H 0.3543 0.4180 -0.0493 0.034 Uiso 1 1 calc R U . . .
C16 C 0.4034(3) 0.3682(3) -0.2197(2) 0.0321(6) Uani 1 1 d . . . . .
H16 H 0.4319 0.4860 -0.2240 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2650(3) 0.0996(3) -0.00034(19) 0.0273(5) Uani 1 1 d . . . . .
B1 B 0.2723(4) 0.2667(3) 0.3297(2) 0.0289(6) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
F2 B1 1.369(3) . ?
F18 B1 1.382(3) . ?
O19 C2 1.319(2) . ?
O19 B1 1.460(3) . ?
N1 C2 1.293(3) . ?
N1 C3 1.384(2) . ?
N20 C3 1.354(3) . ?
N20 C10 1.366(2) . ?
N20 B1 1.572(3) . ?
C2 C17 1.487(3) . ?
C3 C6 1.393(3) . ?
C4 C15 1.421(3) . ?
C4 C5 1.433(3) . ?
C4 C17 1.438(3) . ?
C5 C8 1.414(3) . ?
C5 C13 1.418(3) . ?
C6 C9 1.372(3) . ?
C6 H6 0.9500 . ?
C7 C17 1.373(3) . ?
C7 C14 1.408(3) . ?
C7 H7 0.9500 . ?
C8 C14 1.355(3) . ?
C8 H8 0.9500 . ?
C9 C12 1.394(3) . ?
C9 H9 0.9500 . ?
C10 C12 1.364(3) . ?
C10 H10 0.9500 . ?
C11 C13 1.354(3) . ?
C11 C16 1.404(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.362(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O19 B1 123.73(17) . . ?
C2 N1 C3 118.95(19) . . ?
C3 N20 C10 120.09(19) . . ?
C3 N20 B1 121.35(18) . . ?
C10 N20 B1 118.55(18) . . ?
N1 C2 O19 126.0(2) . . ?
N1 C2 C17 120.7(2) . . ?
O19 C2 C17 113.20(18) . . ?
N20 C3 N1 121.45(19) . . ?
N20 C3 C6 119.83(19) . . ?
N1 C3 C6 118.7(2) . . ?
C15 C4 C5 117.8(2) . . ?
C15 C4 C17 124.51(19) . . ?
C5 C4 C17 117.66(19) . . ?
C8 C5 C13 121.4(2) . . ?
C8 C5 C4 119.6(2) . . ?
C13 C5 C4 118.9(2) . . ?
C9 C6 C3 120.0(2) . . ?
C9 C6 H6 120.0 . . ?
C3 C6 H6 120.0 . . ?
C17 C7 C14 121.7(2) . . ?
C17 C7 H7 119.1 . . ?
C14 C7 H7 119.1 . . ?
C14 C8 C5 121.4(2) . . ?
C14 C8 H8 119.3 . . ?
C5 C8 H8 119.3 . . ?
C6 C9 C12 119.5(2) . . ?
C6 C9 H9 120.3 . . ?
C12 C9 H9 120.3 . . ?
C12 C10 N20 121.4(2) . . ?
C12 C10 H10 119.3 . . ?
N20 C10 H10 119.3 . . ?
C13 C11 C16 119.7(2) . . ?
C13 C11 H11 120.2 . . ?
C16 C11 H11 120.2 . . ?
C10 C12 C9 119.1(2) . . ?
C10 C12 H12 120.4 . . ?
C9 C12 H12 120.4 . . ?
C11 C13 C5 121.5(2) . . ?
C11 C13 H13 119.3 . . ?
C5 C13 H13 119.3 . . ?
C8 C14 C7 119.6(2) . . ?
C8 C14 H14 120.2 . . ?
C7 C14 H14 120.2 . . ?
C16 C15 C4 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C4 C15 H15 119.6 . . ?
C15 C16 C11 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C7 C17 C4 119.85(19) . . ?
C7 C17 C2 117.1(2) . . ?
C4 C17 C2 123.08(19) . . ?
F2 B1 F18 110.98(19) . . ?
F2 B1 O19 110.49(19) . . ?
F18 B1 O19 109.69(18) . . ?
F2 B1 N20 109.28(18) . . ?
F18 B1 N20 108.08(19) . . ?
O19 B1 N20 108.23(18) . . ?

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
C3 N1 C2 O19 3.2(3) . . . . ?
C3 N1 C2 C17 179.21(18) . . . . ?
B1 O19 C2 N1 -6.9(3) . . . . ?
B1 O19 C2 C17 176.83(18) . . . . ?
C10 N20 C3 N1 178.45(19) . . . . ?
B1 N20 C3 N1 -0.9(3) . . . . ?
C10 N20 C3 C6 -2.5(3) . . . . ?
B1 N20 C3 C6 178.2(2) . . . . ?
C2 N1 C3 N20 0.7(3) . . . . ?
C2 N1 C3 C6 -178.3(2) . . . . ?
C15 C4 C5 C8 176.72(19) . . . . ?
C17 C4 C5 C8 -0.1(3) . . . . ?
C15 C4 C5 C13 -1.9(3) . . . . ?
C17 C4 C5 C13 -178.72(19) . . . . ?
N20 C3 C6 C9 3.0(3) . . . . ?
N1 C3 C6 C9 -178.00(18) . . . . ?
C13 C5 C8 C14 176.2(2) . . . . ?
C4 C5 C8 C14 -2.4(3) . . . . ?
C3 C6 C9 C12 -2.0(3) . . . . ?
C3 N20 C10 C12 1.2(3) . . . . ?
B1 N20 C10 C12 -179.5(2) . . . . ?
N20 C10 C12 C9 -0.2(4) . . . . ?
C6 C9 C12 C10 0.6(4) . . . . ?
C16 C11 C13 C5 0.7(3) . . . . ?
C8 C5 C13 C11 -178.0(2) . . . . ?
C4 C5 C13 C11 0.6(3) . . . . ?
C5 C8 C14 C7 1.7(3) . . . . ?
C17 C7 C14 C8 1.5(3) . . . . ?
C5 C4 C15 C16 1.9(3) . . . . ?
C17 C4 C15 C16 178.5(2) . . . . ?
C4 C15 C16 C11 -0.6(3) . . . . ?
C13 C11 C16 C15 -0.7(3) . . . . ?
C14 C7 C17 C4 -4.0(3) . . . . ?
C14 C7 C17 C2 176.00(18) . . . . ?
C15 C4 C17 C7 -173.4(2) . . . . ?
C5 C4 C17 C7 3.3(3) . . . . ?
C15 C4 C17 C2 6.6(3) . . . . ?
C5 C4 C17 C2 -176.79(18) . . . . ?
N1 C2 C17 C7 -148.3(2) . . . . ?
O19 C2 C17 C7 28.2(3) . . . . ?
N1 C2 C17 C4 31.7(3) . . . . ?
O19 C2 C17 C4 -151.8(2) . . . . ?
C2 O19 B1 F2 125.3(2) . . . . ?
C2 O19 B1 F18 -112.0(2) . . . . ?
C2 O19 B1 N20 5.7(3) . . . . ?
C3 N20 B1 F2 -122.5(2) . . . . ?
C10 N20 B1 F2 58.2(3) . . . . ?
C3 N20 B1 F18 116.7(2) . . . . ?
C10 N20 B1 F18 -62.7(3) . . . . ?
C3 N20 B1 O19 -2.1(3) . . . . ?
C10 N20 B1 O19 178.60(17) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;


