# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

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

data_3j
_database_code_depnum_ccdc_archive 'CCDC 1888894'
loop_
_audit_author_name
_audit_author_address
'Nagendra K. Sharma'
;NISER-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;
_audit_creation_date             2018-10-27
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 B F2 N O3'
_chemical_formula_sum            'C9 H8 B F2 N O3'
_chemical_formula_weight         226.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O B F'
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 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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.0433(4)
_cell_length_b                   11.5620(8)
_cell_length_c                   11.6118(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.857(5)
_cell_angle_gamma                90
_cell_volume                     945.50(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5212
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.0930
_cell_measurement_theta_min      3.7760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6207
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.466
_diffrn_reflns_theta_min         5.399
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  18.00   0.50    4.00    --  -38.50 102.00  -2.00  188
  2  ω      4.00  87.00   0.50    4.00    --   49.31-102.00-106.00  166
  3  ω    101.00 176.00   0.50   16.00    --  106.38 102.00  -2.00  150
  4  ω     37.00 112.00   0.50   16.00    --  106.38-102.00-106.00  150
  5  ω    -44.00  31.00   0.50    4.00    --  -38.50  19.00 -60.00  150
  6  ω     38.00 112.00   0.50    4.00    --   49.31  57.00  90.00  148
  7  ω     44.00 120.00   0.50   16.00    --  106.38 -61.00  90.00  152
  8  ω     38.00 110.00   0.50   16.00    --  106.38 -30.00-150.00  144
  9  ω     42.00 122.00   0.50   16.00    --  106.38-125.00 -30.00  160
 10  ω     42.00 111.00   0.50   16.00    --  106.38 -45.00 -60.00  138
 11  ω     93.00 169.00   0.50   16.00    --  106.38  61.00-120.00  152
 12  ω     38.00 109.00   0.50   16.00    --  106.38 -94.00  30.00  142
 13  ω    103.00 175.00   0.50   16.00    --  106.38  30.00   0.00  144
 14  ω    102.00 171.00   0.50   16.00    --  106.38  45.00 -90.00  138
 15  ω     93.00 169.00   0.50   16.00    --  106.38  61.00 150.00  152
 16  ω     26.00  51.00   0.50    4.00    --   49.31  77.00-150.00   50
 17  ω     26.00 114.00   0.50    4.00    --   49.31  77.00 -30.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1024985000
_diffrn_orient_matrix_UB_12      0.0111566000
_diffrn_orient_matrix_UB_13      -0.1176240000
_diffrn_orient_matrix_UB_21      -0.1281190000
_diffrn_orient_matrix_UB_22      0.0952027000
_diffrn_orient_matrix_UB_23      0.0494597000
_diffrn_orient_matrix_UB_31      0.1445792000
_diffrn_orient_matrix_UB_32      0.0925843000
_diffrn_orient_matrix_UB_33      -0.0365047000
_diffrn_oxdiff_ac3_digest_frames 
;
01bac81433a7609429229c326363b65922000264e04
;
_diffrn_oxdiff_ac3_digest_hkl    
;
0104e3d0b2ec15b07b3b9ef20a5f3ccfdb8009
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1701
_reflns_number_total             1880
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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         0.644
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.567
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.1201
_refine_ls_restrained_S_all      1.567
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3423
_refine_ls_wR_factor_ref         0.3485
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3A), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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 0.6250(3) 0.6993(2) 0.20560(18) 0.0699(7) Uani 1 1 d . . . . .
F2 F 0.9403(3) 0.6696(2) 0.19368(17) 0.0721(8) Uani 1 1 d . . . . .
O1 O 0.7529(3) 0.5335(2) 0.29689(18) 0.0548(7) Uani 1 1 d . . . . .
O2 O 0.5339(3) 0.8730(2) 0.4350(2) 0.0589(7) Uani 1 1 d . . . . .
O3 O 0.7522(3) 0.9997(2) 0.4938(3) 0.0687(8) Uani 1 1 d . . . . .
N1 N 0.8138(3) 0.7112(2) 0.38282(19) 0.0495(7) Uani 1 1 d . . . . .
C9 C 0.6990(4) 0.9028(3) 0.4469(2) 0.0496(8) Uani 1 1 d . . . . .
C7 C 0.7896(3) 0.6329(2) 0.4649(2) 0.0452(8) Uani 1 1 d . . . . .
C1 C 0.7516(3) 0.5238(2) 0.4104(2) 0.0467(8) Uani 1 1 d . . . . .
C6 C 0.8016(4) 0.6562(3) 0.5842(3) 0.0551(8) Uani 1 1 d . . . . .
H6 H 0.829406 0.732105 0.604792 0.066 Uiso 1 1 calc R . . . .
C2 C 0.7161(4) 0.4183(3) 0.4605(3) 0.0551(8) Uani 1 1 d . . . . .
H2 H 0.697334 0.356753 0.410020 0.066 Uiso 1 1 calc R . . . .
C8 C 0.8622(4) 0.8305(3) 0.4048(3) 0.0557(8) Uani 1 1 d . . . . .
H8A H 0.909400 0.864484 0.334374 0.067 Uiso 1 1 calc R . . . .
H8B H 0.964148 0.833157 0.461800 0.067 Uiso 1 1 calc R . . . .
C3 C 0.7046(4) 0.3918(3) 0.5781(3) 0.0619(9) Uani 1 1 d . . . . .
H3A H 0.674844 0.315335 0.594887 0.074 Uiso 1 1 calc R . . . .
C5 C 0.7770(4) 0.5796(4) 0.6736(2) 0.0659(10) Uani 1 1 d . . . . .
H5 H 0.794040 0.611161 0.746726 0.079 Uiso 1 1 calc R . . . .
C4 C 0.7311(5) 0.4630(4) 0.6723(3) 0.0659(10) Uani 1 1 d . . . . .
H4 H 0.716220 0.428372 0.743922 0.079 Uiso 1 1 calc R . . . .
B1 B 0.7839(5) 0.6565(3) 0.2631(3) 0.0530(8) Uani 1 1 d . . . . .
H3 H 0.657(9) 1.069(7) 0.513(6) 0.114(19) Uiso 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 1.385(4) . ?
F2 B1 1.383(4) . ?
O1 C1 1.323(3) . ?
O1 B1 1.493(4) . ?
O2 C9 1.219(3) . ?
O3 C9 1.298(4) . ?
O3 H3 1.07(7) . ?
N1 C7 1.328(4) . ?
N1 C8 1.443(4) . ?
N1 B1 1.539(4) . ?
C9 C8 1.508(4) . ?
C7 C1 1.435(4) . ?
C7 C6 1.412(4) . ?
C1 C2 1.376(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.378(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.403(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 H3A 0.9300 . ?
C3 C4 1.379(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.387(6) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 B1 110.3(2) . . ?
C9 O3 H3 124(4) . . ?
C7 N1 C8 123.9(2) . . ?
C7 N1 B1 110.5(2) . . ?
C8 N1 B1 125.5(2) . . ?
O2 C9 O3 124.1(3) . . ?
O2 C9 C8 122.5(3) . . ?
O3 C9 C8 113.4(2) . . ?
N1 C7 C1 108.0(2) . . ?
N1 C7 C6 124.6(3) . . ?
C6 C7 C1 127.5(3) . . ?
O1 C1 C7 111.1(2) . . ?
O1 C1 C2 120.0(3) . . ?
C2 C1 C7 128.8(3) . . ?
C7 C6 H6 116.2 . . ?
C5 C6 C7 127.6(3) . . ?
C5 C6 H6 116.2 . . ?
C1 C2 H2 115.9 . . ?
C1 C2 C3 128.2(3) . . ?
C3 C2 H2 115.9 . . ?
N1 C8 C9 114.0(2) . . ?
N1 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C2 C3 H3A 115.4 . . ?
C4 C3 C2 129.3(3) . . ?
C4 C3 H3A 115.4 . . ?
C6 C5 H5 114.8 . . ?
C6 C5 C4 130.4(3) . . ?
C4 C5 H5 114.8 . . ?
C3 C4 C5 128.1(3) . . ?
C3 C4 H4 115.9 . . ?
C5 C4 H4 115.9 . . ?
F1 B1 O1 110.3(3) . . ?
F1 B1 N1 112.8(3) . . ?
F2 B1 F1 109.0(3) . . ?
F2 B1 O1 112.2(3) . . ?
F2 B1 N1 112.4(3) . . ?
O1 B1 N1 99.9(2) . . ?

_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 5.419
_oxdiff_exptl_absorpt_empirical_full_min 0.193
####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1888899'
loop_
_audit_author_name
_audit_author_address
'Nagendra K. Sharma'
;NISER-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;
_audit_creation_date             2018-10-27
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_chemical_name_systematic        RCS-21
_chemical_formula_moiety         'C11 H12 B F2 N O3'
_chemical_formula_sum            'C11 H12 B F2 N O3'
_chemical_formula_weight         255.04
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00963 0.00408 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.1705(7)
_cell_length_b                   12.9185(4)
_cell_length_c                   7.3648(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.809(3)
_cell_angle_gamma                90
_cell_volume                     1241.45(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4594
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2610
_cell_measurement_theta_min      4.7760
_exptl_absorpt_coefficient_mu    1.005
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.3644
_exptl_crystal_description       needle
_exptl_crystal_F_000             530.1697
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8441
_diffrn_reflns_theta_full        74.4768
_diffrn_reflns_theta_max         74.48
_diffrn_reflns_theta_min         3.39
_diffrn_ambient_temperature      298.0
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9661
_diffrn_measured_fraction_theta_max 0.9661
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00  -6.00   0.50    4.50    --  -38.50 131.00 -63.00  174
  2  ω    -97.00 -10.00   0.50    4.50    --  -38.50 138.00 112.00  174
  3  ω     28.00 104.00   0.50    4.50    --   49.56-131.00-133.00  152
  4  ω     87.00 169.00   0.50   18.00    --  106.38 138.00 112.00  164
  5  ω     43.00 124.00   0.50   18.00    --  106.38-131.00-133.00  162
  6  ω     91.00 170.00   0.50   18.00    --  106.38 131.00 -63.00  158
  7  ω     44.00 128.00   0.50   18.00    --  106.38-138.00  50.00  168
  8  ω   -101.00 -27.00   0.50    4.50    --  -38.50 -57.00 -60.00  148
  9  ω   -103.00 -75.00   0.50    4.50    --  -38.50 -37.00  30.00   56
 10  ω    -70.00 -37.00   0.50    4.50    --  -38.50 -37.00  30.00   66
 11  ω     43.00 113.00   0.50    4.50    --   49.56  57.00 -60.00  140
 12  ω     46.00  71.00   0.50    4.50    --   49.56-138.00  50.00   50
 13  ω    137.00 168.00   0.50   18.00    --  106.38  15.00 120.00   62
 14  ω     73.00  99.00   0.50   18.00    --  106.38 -94.00  60.00   52
 15  ω     43.00  68.00   0.50   18.00    --  106.38 -45.00 150.00   50
 16  ω     46.00 111.00   0.50   18.00    --  106.38 -45.00  30.00  130
 17  ω     50.00  97.00   0.50   18.00    --  106.38 -61.00-180.00   94
 18  ω    103.00 173.00   0.50   18.00    --  106.38  30.00-180.00  140
 19  ω    119.00 153.00   0.50   18.00    --  106.38  45.00-120.00   68
 20  ω     43.00 111.00   0.50   18.00    --  106.38 -45.00 -30.00  136
 21  ω     74.00 110.00   0.50   18.00    --  106.38 -45.00 150.00   72
 22  ω    105.00 171.00   0.50   18.00    --  106.38  45.00-150.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1794
_reflns_number_total             2449
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.4085
_refine_diff_density_min         -0.3611
_refine_diff_density_rms         0.0967
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             13.0484
_refine_ls_goodness_of_fit_ref   1.2109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0974
_refine_ls_restrained_S_all      1.2109
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2898
_refine_ls_wR_factor_ref         0.3107
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O1 O 0.09745(18) 0.45678(17) 0.6592(3) 0.0749(7) Uani 1.000000 .
F1 F 0.1916(2) 0.56187(17) 0.4770(3) 0.1029(8) Uani 1.000000 .
F2 F 0.2410(2) 0.55387(18) 0.7826(3) 0.1039(8) Uani 1.000000 .
N1 N 0.2555(2) 0.39885(17) 0.6025(3) 0.0603(7) Uani 1.000000 .
O2 O 0.4139(2) 0.3430(3) 0.8768(3) 0.1003(10) Uani 1.000000 .
C7 C 0.1968(2) 0.31716(18) 0.6203(2) 0.0519(7) Uani 1.000000 .
O3 O 0.5283(2) 0.3976(3) 0.7074(3) 0.1124(12) Uani 1.000000 .
C1 C 0.0974(2) 0.3553(2) 0.6535(3) 0.0573(8) Uani 1.000000 .
C6 C 0.2246(3) 0.21322(19) 0.6056(3) 0.0594(8) Uani 1.000000 .
H6 H 0.2912(3) 0.20137(19) 0.5815(3) 0.0713(9) Uiso 1.000000 R
C2 C 0.0112(3) 0.3003(3) 0.6784(3) 0.0691(9) Uani 1.000000 .
H2 H -0.0461(3) 0.3395(3) 0.6945(3) 0.0829(10) Uiso 1.000000 R
C5 C 0.1662(3) 0.1263(2) 0.6222(3) 0.0702(9) Uani 1.000000 .
H5 H 0.1989(3) 0.0639(2) 0.6053(3) 0.0843(11) Uiso 1.000000 R
C9 C 0.4362(3) 0.3755(2) 0.7373(4) 0.0681(9) Uani 1.000000 .
C3 C -0.0017(3) 0.1927(3) 0.6826(4) 0.0749(9) Uani 1.000000 .
H3 H -0.0661(3) 0.1703(3) 0.7040(4) 0.0899(11) Uiso 1.000000 R
C8 C 0.3601(3) 0.3948(2) 0.5662(3) 0.0689(9) Uani 1.000000 .
H8a H 0.3667(3) 0.3402(2) 0.4782(3) 0.0827(11) Uiso 1.000000 R
H8b H 0.3769(3) 0.4598(2) 0.5113(3) 0.0827(11) Uiso 1.000000 R
C4 C 0.0662(3) 0.1168(2) 0.6600(4) 0.0771(10) Uani 1.000000 .
H4 H 0.0429(3) 0.0495(2) 0.6713(4) 0.0925(13) Uiso 1.000000 R
B1 B 0.1979(3) 0.4995(2) 0.6303(4) 0.0720(10) Uani 1.000000 .
C10 C 0.6118(5) 0.3871(6) 0.8574(7) 0.128(2) Uani 1.000000 .
C11 C 0.6741(8) 0.3048(6) 0.8297(7) 0.181(4) Uani 1.000000 .
H11a H 0.695(5) 0.310(3) 0.710(4) 0.271(6) Uiso 1.000000 GR
H11b H 0.734(3) 0.306(3) 0.921(6) 0.271(6) Uiso 1.000000 GR
H11c H 0.637(2) 0.2413(7) 0.839(11) 0.271(6) Uiso 1.000000 GR
H10a H 0.6520(5) 0.4502(6) 0.8682(7) 0.153(2) Uiso 1.000000 R
H10b H 0.5837(5) 0.3771(6) 0.9713(7) 0.153(2) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.312(3) . ?
O1 B1 1.475(5) . ?
F1 B1 1.381(4) . ?
F2 B1 1.379(4) . ?
N1 C7 1.325(3) . ?
N1 C8 1.439(4) . ?
N1 B1 1.533(4) . ?
O2 C9 1.184(3) . ?
C7 C1 1.450(4) . ?
C7 C6 1.400(3) . ?
O3 C9 1.295(4) . ?
O3 C10 1.455(6) . ?
C1 C2 1.373(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.376(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.400(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.387(5) . ?
C9 C8 1.520(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.353(5) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C4 H4 0.9300 . ?
C10 C11 1.375(9) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C1 111.4(2) . . ?
C8 N1 C7 125.1(2) . . ?
B1 N1 C7 110.8(3) . . ?
B1 N1 C8 124.0(3) . . ?
C1 C7 N1 107.4(2) . . ?
C6 C7 N1 126.4(3) . . ?
C6 C7 C1 126.2(3) . . ?
C10 O3 C9 118.6(3) . . ?
C7 C1 O1 110.4(2) . . ?
C2 C1 O1 120.6(3) . . ?
C2 C1 C7 129.0(3) . . ?
H6 C6 C7 115.84(18) . . ?
C5 C6 C7 128.3(3) . . ?
C5 C6 H6 115.84(19) . . ?
H2 C2 C1 115.81(18) . . ?
C3 C2 C1 128.4(3) . . ?
C3 C2 H2 115.8(2) . . ?
H5 C5 C6 114.82(19) . . ?
C4 C5 C6 130.4(3) . . ?
C4 C5 H5 114.82(17) . . ?
O3 C9 O2 125.1(3) . . ?
C8 C9 O2 124.4(3) . . ?
C8 C9 O3 110.5(2) . . ?
H3 C3 C2 115.4(2) . . ?
C4 C3 C2 129.2(3) . . ?
C4 C3 H3 115.4(2) . . ?
C9 C8 N1 113.0(2) . . ?
H8a C8 N1 108.97(15) . . ?
H8a C8 C9 108.97(17) . . ?
H8b C8 N1 108.97(13) . . ?
H8b C8 C9 108.97(16) . . ?
H8b C8 H8a 107.8 . . ?
C3 C4 C5 128.4(3) . . ?
H4 C4 C5 115.78(17) . . ?
H4 C4 C3 115.8(2) . . ?
F1 B1 O1 112.4(3) . . ?
F2 B1 O1 110.6(3) . . ?
F2 B1 F1 109.9(3) . . ?
N1 B1 O1 99.9(2) . . ?
N1 B1 F1 111.2(3) . . ?
N1 B1 F2 112.6(3) . . ?
C11 C10 O3 111.4(5) . . ?
H10a C10 O3 109.4(3) . . ?
H10a C10 C11 109.4(6) . . ?
H10b C10 O3 109.4(3) . . ?
H10b C10 C11 109.4(4) . . ?
H10b C10 H10a 108.0 . . ?
H11a C11 C10 109.5 . . ?
H11b C11 C10 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C10 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?

_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
;
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1888896'
loop_
_audit_author_name
_audit_author_address
'Nagendra K. Sharma'
;NISER-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;
_audit_creation_date             2018-10-27
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_chemical_name_systematic        NKS_RCS_ALA
_chemical_formula_moiety         'C12 H14 B F2 N O3'
_chemical_formula_sum            'C12 H14 B F2 N O3'
_chemical_formula_weight         269.07
_chemical_oxdiff_formula         'C96 H112 B8 F16 N8 O24 '
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00963 0.00408 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   13.5273(5)
_cell_length_b                   7.7581(4)
_cell_length_c                   24.7812(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2600.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3075
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8980
_cell_measurement_theta_min      3.5890
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.3742
_exptl_crystal_description       needle
_exptl_crystal_F_000             1124.4858
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10196
_diffrn_reflns_theta_full        74.4605
_diffrn_reflns_theta_max         74.46
_diffrn_reflns_theta_min         3.57
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9571
_diffrn_measured_fraction_theta_max 0.9571
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -16.00   0.50    8.00    --  -38.50 139.00 160.00  164
  2  ω    -50.00 -25.00   0.50    8.00    --  -38.50 130.00 -13.00   50
  3  ω     42.00  67.00   0.50    8.00    --   49.31-130.00 -85.00   50
  4  ω     54.00  93.00   0.50    8.00    --   49.31-139.00 100.00   78
  5  ω     86.00 111.00   0.50   30.00    --  106.38-139.00 100.00   50
  6  ω     99.00 170.00   0.50   30.00    --  106.38 130.00 -13.00  142
  7  ω    123.00 168.00   0.50   30.00    --  106.38 139.00 160.00   90
  8  ω   -100.00 -44.00   0.50    8.00    --  -38.50 -57.00 -90.00  112
  9  ω     -7.00  20.00   0.50    8.00    --  -38.50  77.00-150.00   54
 10  ω    -61.00 -34.00   0.50    8.00    --  -38.50  77.00-150.00   54
 11  ω     13.00  61.00   0.50    8.00    --   49.31 -57.00-120.00   96
 12  ω    113.00 171.00   0.50   30.00    --  106.38 125.00-150.00  116
 13  ω     89.00 114.00   0.50   30.00    --  106.38 -61.00  60.00   50
 14  ω    104.00 175.00   0.50   30.00    --  106.38  30.00 -90.00  142
 15  ω    142.00 168.00   0.50   30.00    --  106.38  45.00 -30.00   52
 16  ω    104.00 129.00   0.50   30.00    --  106.38  45.00 -30.00   50
 17  ω     47.00  88.00   0.50   30.00    --  106.38 -61.00  60.00   82
 18  ω     68.00  95.00   0.50   30.00    --  106.38 -30.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0798606000
_diffrn_orient_matrix_UB_12      0.0545941000
_diffrn_orient_matrix_UB_13      0.0409145000
_diffrn_orient_matrix_UB_21      0.0713028000
_diffrn_orient_matrix_UB_22      0.0407908000
_diffrn_orient_matrix_UB_23      -0.0467663000
_diffrn_orient_matrix_UB_31      -0.0388228000
_diffrn_orient_matrix_UB_32      0.1865344000
_diffrn_orient_matrix_UB_33      -0.0017715000
_diffrn_oxdiff_ac3_digest_frames 
;
01c0cbd288793b922a3a12069b0c882a4400025ed33
;
_diffrn_oxdiff_ac3_digest_hkl    
;
015e171b5f4e6dfc99157bc9af0c596509beab
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              0
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                1454
_reflns_number_total             2546
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2916
_refine_diff_density_min         -0.4282
_refine_diff_density_rms         0.0884
_refine_ls_d_res_high            0.8002
_refine_ls_d_res_low             12.3906
_refine_ls_goodness_of_fit_ref   1.1260
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.0922
_refine_ls_restrained_S_all      1.1260
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2806
_refine_ls_wR_factor_ref         0.3336
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C12(H12a,H12b,H12c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O3 O 0.6674(2) 0.2296(3) 0.21783(13) 0.0740(8) Uani 1.000000 .
O2 O 0.6785(2) 0.4333(3) 0.28037(13) 0.0782(9) Uani 1.000000 .
F2 F 0.46165(19) 0.3980(4) 0.36225(15) 0.1079(11) Uani 1.000000 .
F1 F 0.44941(19) 0.1322(4) 0.39780(16) 0.1069(11) Uani 1.000000 .
O1 O 0.5533(2) 0.3350(4) 0.44014(15) 0.0873(10) Uani 1.000000 .
N1 N 0.60816(19) 0.2184(4) 0.35915(15) 0.0638(9) Uani 1.000000 .
C10 C 0.6575(2) 0.2893(4) 0.26691(19) 0.0636(10) Uani 1.000000 .
C7 C 0.6860(3) 0.2503(4) 0.39103(17) 0.0605(10) Uani 1.000000 .
C6 C 0.7856(3) 0.2223(5) 0.3768(2) 0.0725(11) Uani 1.000000 .
C1 C 0.6506(3) 0.3223(5) 0.4411(2) 0.0724(11) Uani 1.000000 .
C8 C 0.6181(3) 0.1513(4) 0.3050(2) 0.0690(11) Uani 1.000000 .
C11 C 0.7134(3) 0.3426(6) 0.1780(2) 0.0815(13) Uani 1.000000 .
C5 C 0.8683(3) 0.2534(5) 0.4074(3) 0.0869(14) Uani 1.000000 .
C2 C 0.7027(4) 0.3774(6) 0.4844(2) 0.0902(14) Uani 1.000000 .
C9 C 0.5220(3) 0.0751(6) 0.2836(2) 0.0906(15) Uani 1.000000 .
C12 C 0.6932(4) 0.2718(6) 0.1242(2) 0.0905(15) Uani 1.000000 .
C4 C 0.8778(4) 0.3239(7) 0.4587(3) 0.1009(18) Uani 1.000000 .
C3 C 0.8047(5) 0.3768(7) 0.4925(3) 0.0996(17) Uani 1.000000 .
B1 B 0.5115(3) 0.2696(6) 0.3894(3) 0.0787(14) Uani 1.000000 .
H6 H 0.7966(3) 0.1774(5) 0.3425(2) 0.0870(14) Uiso 1.000000 R
H8 H 0.6670(3) 0.0581(4) 0.3062(2) 0.0828(14) Uiso 1.000000 R
H11a H 0.6863(3) 0.4581(6) 0.1809(2) 0.0978(15) Uiso 1.000000 R
H11b H 0.7841(3) 0.3487(6) 0.1841(2) 0.0978(15) Uiso 1.000000 R
H5 H 0.9277(3) 0.2222(5) 0.3911(3) 0.1043(17) Uiso 1.000000 R
H2 H 0.6653(4) 0.4218(6) 0.5127(2) 0.1083(17) Uiso 1.000000 R
H9a H 0.5031(17) -0.021(4) 0.3055(10) 0.136(2) Uiso 1.000000 GR
H9b H 0.4711(8) 0.1611(18) 0.2847(17) 0.136(2) Uiso 1.000000 GR
H9c H 0.5315(9) 0.038(5) 0.2470(6) 0.136(2) Uiso 1.000000 GR
H12a H 0.730(3) 0.336(4) 0.0976(3) 0.136(2) Uiso 1.000000 GR
H12b H 0.713(3) 0.1530(17) 0.1231(6) 0.136(2) Uiso 1.000000 GR
H12c H 0.6238(6) 0.280(5) 0.1166(7) 0.136(2) Uiso 1.000000 GR
H4 H 0.9421(4) 0.3363(7) 0.4715(3) 0.121(2) Uiso 1.000000 R
H3 H 0.8258(5) 0.4187(7) 0.5257(3) 0.120(2) Uiso 1.000000 R


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
O3 C10 1.308(5) . ?
O3 C11 1.460(5) . ?
O2 C10 1.200(4) . ?
F2 B1 1.378(6) . ?
F1 B1 1.373(5) . ?
O1 C1 1.320(5) . ?
O1 B1 1.470(7) . ?
N1 C7 1.339(5) . ?
N1 C8 1.446(6) . ?
N1 B1 1.558(5) . ?
C10 C8 1.524(6) . ?
C7 C6 1.409(5) . ?
C7 C1 1.443(6) . ?
C6 C5 1.373(6) . ?
C6 H6 0.9300 . ?
C1 C2 1.354(7) . ?
C8 C9 1.523(5) . ?
C8 H8 0.9800 . ?
C11 C12 1.467(7) . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C5 C4 1.390(9) . ?
C5 H5 0.9300 . ?
C2 C3 1.395(9) . ?
C2 H2 0.9300 . ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9c 0.9600 . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C4 C3 1.359(9) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 C10 117.4(3) . . ?
B1 O1 C1 111.9(3) . . ?
C8 N1 C7 122.8(3) . . ?
B1 N1 C7 109.2(4) . . ?
B1 N1 C8 128.0(3) . . ?
O2 C10 O3 124.3(4) . . ?
C8 C10 O3 111.2(3) . . ?
C8 C10 O2 124.4(4) . . ?
C6 C7 N1 125.1(4) . . ?
C1 C7 N1 108.5(3) . . ?
C1 C7 C6 126.3(4) . . ?
C5 C6 C7 127.9(5) . . ?
H6 C6 C7 116.1(3) . . ?
H6 C6 C5 116.1(3) . . ?
C7 C1 O1 110.1(4) . . ?
C2 C1 O1 120.6(5) . . ?
C2 C1 C7 129.2(4) . . ?
C10 C8 N1 110.7(3) . . ?
C9 C8 N1 112.6(3) . . ?
C9 C8 C10 110.8(4) . . ?
H8 C8 N1 107.48(19) . . ?
H8 C8 C10 107.48(18) . . ?
H8 C8 C9 107.5(2) . . ?
C12 C11 O3 108.1(4) . . ?
H11a C11 O3 110.1(2) . . ?
H11a C11 C12 110.1(3) . . ?
H11b C11 O3 110.1(2) . . ?
H11b C11 C12 110.1(3) . . ?
H11b C11 H11a 108.4 . . ?
C4 C5 C6 130.5(5) . . ?
H5 C5 C6 114.8(3) . . ?
H5 C5 C4 114.8(3) . . ?
C3 C2 C1 128.8(6) . . ?
H2 C2 C1 115.6(3) . . ?
H2 C2 C3 115.6(4) . . ?
H9a C9 C8 109.5 . . ?
H9b C9 C8 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C8 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C3 C4 C5 128.0(5) . . ?
H4 C4 C5 116.0(3) . . ?
H4 C4 C3 116.0(3) . . ?
C4 C3 C2 129.3(5) . . ?
H3 C3 C2 115.4(4) . . ?
H3 C3 C4 115.4(3) . . ?
F1 B1 F2 109.6(4) . . ?
O1 B1 F2 110.9(4) . . ?
O1 B1 F1 111.9(5) . . ?
N1 B1 F2 111.1(4) . . ?
N1 B1 F1 112.9(4) . . ?
N1 B1 O1 100.2(3) . . ?

_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 5.299
_oxdiff_exptl_absorpt_empirical_full_min 0.198
####################################################################### 
# 
# 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_3h
_database_code_depnum_ccdc_archive 'CCDC 1888895'
loop_
_audit_author_name
_audit_author_address
'Nagendra K. Sharma'
;NISER-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;
_audit_creation_date             2018-10-22
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_chemical_name_systematic        triclinic
_chemical_formula_moiety         'C13 H11 B F2 N2 O'
_chemical_formula_sum            'C13 H11 B F2 N2 O'
_chemical_formula_weight         260.07
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00963 0.00408 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.8495(2)
_cell_length_b                   9.1023(2)
_cell_length_c                   9.2653(2)
_cell_angle_alpha                62.940(2)
_cell_angle_beta                 89.372(2)
_cell_angle_gamma                69.175(2)
_cell_volume                     610.93(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6984
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.9900
_cell_measurement_theta_min      5.4140
_exptl_absorpt_coefficient_mu    0.937
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.4136
_exptl_crystal_description       needle
_exptl_crystal_F_000             269.0055
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9421
_diffrn_reflns_theta_full        75.3367
_diffrn_reflns_theta_max         75.34
_diffrn_reflns_theta_min         5.44
_diffrn_ambient_temperature      296.0
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9774
_diffrn_measured_fraction_theta_max 0.9774
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  28.00   0.50    0.20    --  -38.50  37.00   6.00  140
  2  ω   -105.00 -35.00   0.50    0.20    --  -38.50 -37.00-149.00  140
  3  ω    -17.00  53.00   0.50    0.20    --   49.31 -37.00-149.00  140
  4  ω     46.00 116.00   0.50    0.20    --   49.31  37.00   6.00  140
  5  ω     36.00 106.00   0.50    1.00    --  102.63 -37.00-149.00  140
  6  ω    100.00 169.00   0.50    1.00    --  102.63  37.00   6.00  138
  7  ω   -105.00 -35.00   0.50    0.20    --  -38.50 -37.00 150.00  140
  8  ω     24.00 100.00   0.50    0.20    --   49.31-125.00  60.00  152
  9  ω     38.00 112.00   0.50    0.20    --   49.31  57.00-150.00  148
 10  ω    -20.00  55.00   0.50    0.20    --   49.31 -19.00-120.00  150
 11  ω     98.00 167.00   0.50    1.00    --  102.63  45.00-150.00  138
 12  ω     34.00 110.00   0.50    1.00    --  102.63 -94.00 -90.00  152
 13  ω     38.00 118.00   0.50    1.00    --  102.63-125.00-150.00  160
 14  ω     40.00 116.00   0.50    1.00    --  102.63 -61.00 150.00  152
 15  ω     38.00 118.00   0.50    1.00    --  102.63-125.00 -60.00  160
 16  ω     40.00 116.00   0.50    1.00    --  102.63 -61.00   0.00  152
 17  ω     38.00 118.00   0.50    1.00    --  102.63-125.00  30.00  160
 18  ω     34.00 111.00   0.50    1.00    --  102.63 -15.00  30.00  154
 19  ω     98.00 167.00   0.50    1.00    --  102.63  45.00  60.00  138
 20  ω     34.00 110.00   0.50    1.00    --  102.63 -94.00 150.00  152
 21  ω     35.00 106.00   0.50    1.00    --  102.63 -30.00  60.00  142
 22  ω     35.00 106.00   0.50    1.00    --  102.63 -30.00-120.00  142
 23  ω     98.00 167.00   0.50    1.00    --  102.63  45.00-180.00  138
 24  ω     98.00 167.00   0.50    1.00    --  102.63  45.00-120.00  138
 25  ω     38.00 107.00   0.50    1.00    --  102.63 -45.00-120.00  138
 26  ω     38.00 126.00   0.50    1.00    --  102.63 -77.00   0.00  176
 27  ω     26.00 114.00   0.50    0.20    --   49.31  77.00 -90.00  176
 28  ω     26.00 114.00   0.50    0.20    --   49.31  77.00  30.00  176
 29  ω     26.00 114.00   0.50    0.20    --   49.31  77.00 150.00  176
 30  ω     26.00 114.00   0.50    0.20    --   49.31  77.00 -30.00  176
 31  ω     26.00 114.00   0.50    0.20    --   49.31  77.00  90.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -9
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2200
_reflns_number_total             2469
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.1187
_refine_diff_density_min         -0.2152
_refine_diff_density_rms         0.0472
_refine_ls_d_res_high            0.7969
_refine_ls_d_res_low             8.1345
_refine_ls_goodness_of_fit_ref   1.1434
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.1434
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.0662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1034
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C3(H3), C5(H5), C11(H11), C4(H4), C2(H2)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
F2 F 0.67201(10) 0.34826(13) 0.66065(13) 0.0711(3) Uani 1.000000 .
F1 F 0.76260(10) 0.04866(13) 0.81832(13) 0.0787(3) Uani 1.000000 .
O1 O 0.56709(11) 0.18991(14) 0.57520(12) 0.0563(3) Uani 1.000000 .
N2 N 0.47567(11) 0.22422(13) 0.79712(12) 0.0420(2) Uani 1.000000 .
C8 C 0.46273(15) 0.23830(17) 0.94737(15) 0.0482(3) Uani 1.000000 .
H8a H 0.42023(15) 0.15238(17) 1.02173(15) 0.0579(3) Uiso 1.000000 R
H8b H 0.57183(15) 0.20623(17) 1.00077(15) 0.0579(3) Uiso 1.000000 R
C10 C 0.35277(18) 0.57674(19) 0.78726(17) 0.0563(3) Uani 1.000000 .
H10 H 0.42055(18) 0.56991(19) 0.71116(17) 0.0676(4) Uiso 1.000000 R
C6 C 0.3276(2) 0.2114(2) 0.44757(17) 0.0589(3) Uani 1.000000 .
H6 H 0.3869(2) 0.1977(2) 0.36787(17) 0.0706(4) Uiso 1.000000 R
C3 C 0.06607(16) 0.2523(2) 0.6697(2) 0.0610(4) Uani 1.000000 .
H3 H -0.02674(16) 0.2618(2) 0.7187(2) 0.0732(4) Uiso 1.000000 R
C5 C 0.1644(2) 0.2303(2) 0.4252(2) 0.0682(4) Uani 1.000000 .
H5 H 0.1292(2) 0.2305(2) 0.3310(2) 0.0819(5) Uiso 1.000000 R
C11 C 0.2505(2) 0.7406(2) 0.7696(2) 0.0652(4) Uani 1.000000 .
H11 H 0.2480(2) 0.8463(2) 0.6812(2) 0.0782(5) Uiso 1.000000 R
C12 C 0.1526(2) 0.7461(2) 0.8839(2) 0.0700(4) Uani 1.000000 .
H12 H 0.075(2) 0.863(3) 0.876(2) 0.0840(5) Uiso 1.000000 .
C4 C 0.04929(19) 0.2487(2) 0.5222(2) 0.0687(4) Uani 1.000000 .
H4 H -0.05356(19) 0.2603(2) 0.4848(2) 0.0824(5) Uiso 1.000000 R
C13 C 0.1616(2) 0.5869(3) 1.0115(3) 0.0818(5) Uani 1.000000 .
B1 B 0.62942(17) 0.2020(2) 0.7153(2) 0.0518(3) Uani 1.000000 .
C1 C 0.35365(13) 0.22898(14) 0.71122(14) 0.0386(2) Uani 1.000000 .
N1 N 0.25972(18) 0.42538(18) 1.03178(17) 0.0670(3) Uani 1.000000 .
C9 C 0.35313(14) 0.42325(17) 0.91919(14) 0.0433(3) Uani 1.000000 .
C7 C 0.41132(15) 0.21038(16) 0.57163(15) 0.0446(3) Uani 1.000000 .
C2 C 0.19734(15) 0.24406(18) 0.75391(17) 0.0484(3) Uani 1.000000 .
H2 H 0.18171(15) 0.24900(18) 0.85128(17) 0.0581(4) Uiso 1.000000 R
H13 H 0.094(3) 0.582(3) 1.100(3) 0.111(7) Uiso 1.000000 .


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 1.3824(18) . ?
F1 B1 1.3750(18) . ?
O1 B1 1.4798(19) . ?
O1 C7 1.3224(15) . ?
N2 C8 1.4547(15) . ?
N2 B1 1.5454(16) . ?
N2 C1 1.3249(15) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C8 C9 1.5124(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(2) . ?
C10 C9 1.3745(19) . ?
C6 H6 0.9300 . ?
C6 C5 1.398(2) . ?
C6 C7 1.3692(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(2) . ?
C3 C2 1.3669(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.367(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(2) . ?
C12 H12 1.01(2) . ?
C12 C13 1.366(3) . ?
C4 H4 0.9300 . ?
C13 N1 1.340(2) . ?
C13 H13 1.00(2) . ?
C1 C7 1.4440(16) . ?
C1 C2 1.4111(16) . ?
N1 C9 1.3267(16) . ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 B1 111.32(9) . . ?
B1 N2 C8 125.88(10) . . ?
C1 N2 C8 123.52(10) . . ?
C1 N2 B1 110.60(10) . . ?
H8a C8 N2 108.80(6) . . ?
H8b C8 N2 108.80(6) . . ?
H8b C8 H8a 107.7 . . ?
C9 C8 N2 113.78(10) . . ?
C9 C8 H8a 108.80(7) . . ?
C9 C8 H8b 108.80(6) . . ?
C11 C10 H10 120.54(9) . . ?
C9 C10 H10 120.54(8) . . ?
C9 C10 C11 118.93(13) . . ?
C5 C6 H6 115.81(9) . . ?
C7 C6 H6 115.81(8) . . ?
C7 C6 C5 128.38(14) . . ?
C4 C3 H3 114.89(9) . . ?
C2 C3 H3 114.89(8) . . ?
C2 C3 C4 130.23(14) . . ?
H5 C5 C6 115.39(9) . . ?
C4 C5 C6 129.23(14) . . ?
C4 C5 H5 115.39(8) . . ?
H11 C11 C10 120.45(9) . . ?
C12 C11 C10 119.09(15) . . ?
C12 C11 H11 120.45(10) . . ?
H12 C12 C11 122.0(11) . . ?
C13 C12 C11 118.05(15) . . ?
C13 C12 H12 119.9(11) . . ?
C5 C4 C3 128.40(13) . . ?
H4 C4 C3 115.80(9) . . ?
H4 C4 C5 115.80(8) . . ?
N1 C13 C12 124.18(16) . . ?
H13 C13 C12 122.0(13) . . ?
H13 C13 N1 113.9(13) . . ?
F1 B1 F2 109.33(11) . . ?
O1 B1 F2 111.08(12) . . ?
O1 B1 F1 111.77(12) . . ?
N2 B1 F2 112.59(11) . . ?
N2 B1 F1 112.14(12) . . ?
N2 B1 O1 99.69(9) . . ?
C7 C1 N2 107.98(10) . . ?
C2 C1 N2 125.15(11) . . ?
C2 C1 C7 126.85(11) . . ?
C9 N1 C13 116.77(14) . . ?
C10 C9 C8 122.00(11) . . ?
N1 C9 C8 115.01(11) . . ?
N1 C9 C10 122.98(12) . . ?
C6 C7 O1 120.83(12) . . ?
C1 C7 O1 110.32(10) . . ?
C1 C7 C6 128.85(12) . . ?
C1 C2 C3 127.97(13) . . ?
H2 C2 C3 116.02(8) . . ?
H2 C2 C1 116.02(7) . . ?

_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
;
####################################################################### 
# 
# 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_3i
_database_code_depnum_ccdc_archive 'CCDC 1888898'
loop_
_audit_author_name
_audit_author_address
'Nagendra K. Sharma'
;NISER-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;
_audit_creation_date             2018-10-27
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_chemical_name_systematic        RCS-48
_chemical_formula_moiety         'C16 H11 B F2 N2 O'
_chemical_formula_sum            'C16 H11 B F2 N2 O'
_chemical_formula_weight         296.10
_chemical_oxdiff_formula         'C64 H44 B4 F8 N8 O4 '
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.0792(4)
_cell_length_b                   7.4313(4)
_cell_length_c                   26.3653(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.772(5)
_cell_angle_gamma                90
_cell_volume                     1377.34(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5659
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.6430
_cell_measurement_theta_min      3.9990
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic reddish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.4277
_exptl_crystal_description       needle
_exptl_crystal_F_000             608.3596
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.0002
_exptl_crystal_size_min          0.0001
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13111
_diffrn_reflns_theta_full        26.3657
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.45
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8227
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  68.00   0.50   36.03    --    3.67  42.00 170.00   88
  2  ω    -68.00  -4.00   0.50   36.03    --   -3.98 -42.00  18.00  128
  3  ω     -4.00  34.00   0.50   36.03    --    3.67 -99.00  60.00   76
  4  ω      1.00  27.00   0.50   36.03    --   -3.98 -99.00-120.00   52
  5  ω    -65.00   6.00   0.50   36.03    --   -3.98 -57.00 -90.00  142
  6  ω    -15.00  56.00   0.50   36.03    --   -3.98  57.00-150.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0663285000
_diffrn_orient_matrix_UB_12      0.0710187000
_diffrn_orient_matrix_UB_13      0.0011177000
_diffrn_orient_matrix_UB_21      -0.0710442000
_diffrn_orient_matrix_UB_22      -0.0524710000
_diffrn_orient_matrix_UB_23      -0.0143411000
_diffrn_orient_matrix_UB_31      -0.0271557000
_diffrn_orient_matrix_UB_32      -0.0362392000
_diffrn_orient_matrix_UB_33      0.0229508000
_diffrn_oxdiff_ac3_digest_frames 
;
016c776e7dadc1c278894037c0d999e091000255313
;
_diffrn_oxdiff_ac3_digest_hkl    
;
015161a5a47863a410a3b9c266e7a6bd001842
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                2436
_reflns_number_total             2802
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.1952
_refine_diff_density_min         -0.2249
_refine_diff_density_rms         0.0345
_refine_ls_d_res_high            0.8002
_refine_ls_d_res_low             5.9096
_refine_ls_goodness_of_fit_ref   0.8420
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      0.8420
_refine_ls_shift/su_max          0.0017
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.1867
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C12(H12), C2(H2), C14(H14), C5(H5), C10(H10), C16(H16),
 C15(H15), C3(H3), C4(H4)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
F2 F 0.81989(14) 0.33584(18) 0.38804(4) 0.0755(4) Uani 1.000000 .
O1 O 0.70569(14) 0.12758(17) 0.32472(4) 0.0580(3) Uani 1.000000 .
F1 F 0.75489(17) 0.05487(19) 0.41242(5) 0.0947(5) Uani 1.000000 .
N1 N 0.48858(15) 0.23866(14) 0.37592(4) 0.0409(3) Uani 1.000000 .
N2 N 0.33268(17) 0.58412(15) 0.36962(5) 0.0490(3) Uani 1.000000 .
C8 C 0.39954(17) 0.31199(17) 0.41723(4) 0.0386(3) Uani 1.000000 .
C17 C 0.32194(17) 0.48907(17) 0.41326(5) 0.0388(3) Uani 1.000000 .
C7 C 0.39740(18) 0.20811(15) 0.32980(5) 0.0383(3) Uani 1.000000 .
C13 C 0.24104(18) 0.5590(2) 0.45584(5) 0.0469(4) Uani 1.000000 .
C6 C 0.20190(19) 0.22862(18) 0.31522(5) 0.0438(4) Uani 1.000000 .
H6 H 0.13068(19) 0.26566(18) 0.34080(5) 0.0526(4) Uiso 1.000000 R
C1 C 0.53700(19) 0.14061(17) 0.29803(5) 0.0454(4) Uani 1.000000 .
C9 C 0.3974(2) 0.2147(2) 0.46089(5) 0.0484(4) Uani 1.000000 .
H9 H 0.4494(2) 0.0997(2) 0.46303(5) 0.0581(4) Uiso 1.000000 R
C12 C 0.2422(2) 0.4536(2) 0.50053(5) 0.0562(4) Uani 1.000000 .
H12 H 0.1907(2) 0.5001(2) 0.52864(5) 0.0675(5) Uiso 1.000000 R
C2 C 0.5117(2) 0.0986(2) 0.24714(6) 0.0563(4) Uani 1.000000 .
H2 H 0.6202(2) 0.0608(2) 0.23344(6) 0.0675(5) Uiso 1.000000 R
C14 C 0.1649(2) 0.7345(2) 0.45084(8) 0.0635(5) Uani 1.000000 .
H14 H 0.1089(2) 0.7862(2) 0.47752(8) 0.0763(6) Uiso 1.000000 R
C5 C 0.1022(2) 0.2012(2) 0.26817(6) 0.0565(4) Uani 1.000000 .
H5 H -0.0281(2) 0.2210(2) 0.26642(6) 0.0678(5) Uiso 1.000000 R
C10 C 0.3170(2) 0.2869(3) 0.50286(5) 0.0584(4) Uani 1.000000 .
H10 H 0.3156(2) 0.2188(3) 0.53241(5) 0.0701(5) Uiso 1.000000 R
C16 C 0.2610(3) 0.7477(2) 0.36780(7) 0.0630(5) Uani 1.000000 .
H16 H 0.2692(3) 0.8149(2) 0.33838(7) 0.0756(6) Uiso 1.000000 R
C15 C 0.1738(3) 0.8273(2) 0.40689(8) 0.0709(5) Uani 1.000000 .
H15 H 0.1224(3) 0.9423(2) 0.40288(8) 0.0851(6) Uiso 1.000000 R
C3 C 0.3473(3) 0.1045(2) 0.21332(6) 0.0629(5) Uani 1.000000 .
H3 H 0.3616(3) 0.0749(2) 0.17971(6) 0.0754(5) Uiso 1.000000 R
C4 C 0.1665(3) 0.1478(3) 0.22228(6) 0.0678(5) Uani 1.000000 .
H4 H 0.0741(3) 0.1408(3) 0.19419(6) 0.0813(6) Uiso 1.000000 R
B1 B 0.7028(3) 0.1891(3) 0.37832(7) 0.0548(5) Uani 1.000000 .


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 1.376(2) . ?
O1 C1 1.3163(17) . ?
O1 B1 1.488(2) . ?
F1 B1 1.364(2) . ?
N1 C8 1.4293(15) . ?
N1 C7 1.3271(17) . ?
N1 B1 1.5547(19) . ?
N2 C17 1.3598(17) . ?
N2 C16 1.316(2) . ?
C8 C17 1.4251(18) . ?
C8 C9 1.3607(18) . ?
C17 C13 1.4176(18) . ?
C7 C6 1.4004(18) . ?
C7 C1 1.4579(17) . ?
C13 C12 1.414(2) . ?
C13 C14 1.412(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.368(2) . ?
C1 C2 1.369(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.409(2) . ?
C12 H12 0.9300 . ?
C12 C10 1.346(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.356(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.399(2) . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.394(3) . ?
C15 H15 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.367(3) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C1 111.84(11) . . ?
C7 N1 C8 123.56(11) . . ?
B1 N1 C8 125.11(10) . . ?
B1 N1 C7 111.32(10) . . ?
C16 N2 C17 116.81(13) . . ?
C17 C8 N1 119.80(11) . . ?
C9 C8 N1 119.47(12) . . ?
C9 C8 C17 120.66(12) . . ?
C8 C17 N2 118.83(11) . . ?
C13 C17 N2 123.21(12) . . ?
C13 C17 C8 117.94(12) . . ?
C6 C7 N1 126.24(11) . . ?
C1 C7 N1 107.21(11) . . ?
C1 C7 C6 126.48(12) . . ?
C12 C13 C17 119.59(13) . . ?
C14 C13 C17 116.76(14) . . ?
C14 C13 C12 123.65(13) . . ?
H6 C6 C7 115.84(7) . . ?
C5 C6 C7 128.33(13) . . ?
C5 C6 H6 115.84(9) . . ?
C7 C1 O1 110.60(12) . . ?
C2 C1 O1 120.86(13) . . ?
C2 C1 C7 128.52(14) . . ?
H9 C9 C8 119.74(8) . . ?
C10 C9 C8 120.53(14) . . ?
C10 C9 H9 119.74(9) . . ?
H12 C12 C13 119.62(8) . . ?
C10 C12 C13 120.76(12) . . ?
C10 C12 H12 119.62(8) . . ?
H2 C2 C1 115.52(9) . . ?
C3 C2 C1 128.95(14) . . ?
C3 C2 H2 115.52(9) . . ?
H14 C14 C13 120.21(10) . . ?
C15 C14 C13 119.59(14) . . ?
C15 C14 H14 120.21(9) . . ?
H5 C5 C6 115.09(9) . . ?
C4 C5 C6 129.82(15) . . ?
C4 C5 H5 115.09(10) . . ?
C12 C10 C9 120.52(13) . . ?
H10 C10 C9 119.74(9) . . ?
H10 C10 C12 119.74(8) . . ?
H16 C16 N2 117.71(10) . . ?
C15 C16 N2 124.58(16) . . ?
C15 C16 H16 117.71(10) . . ?
C16 C15 C14 119.02(15) . . ?
H15 C15 C14 120.49(9) . . ?
H15 C15 C16 120.49(10) . . ?
H3 C3 C2 115.45(9) . . ?
C4 C3 C2 129.11(14) . . ?
C4 C3 H3 115.45(9) . . ?
C3 C4 C5 128.53(15) . . ?
H4 C4 C5 115.73(10) . . ?
H4 C4 C3 115.73(9) . . ?
O1 B1 F2 110.19(14) . . ?
F1 B1 F2 110.29(15) . . ?
F1 B1 O1 111.63(15) . . ?
N1 B1 F2 112.53(13) . . ?
N1 B1 O1 99.01(11) . . ?
N1 B1 F1 112.75(14) . . ?

_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 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.620
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1888897'
loop_
_audit_author_name
_audit_author_address
'Nagendra K. Sharma'
;NISER-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;
_audit_creation_date             2018-11-24
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H16 B F2 N O3)'
_chemical_formula_sum            'C26 H32 B2 F4 N2 O6'
_chemical_formula_weight         566.15
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H32 B2 F4 N4 O6 '
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 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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.1582(2)
_cell_length_b                   9.4094(2)
_cell_length_c                   9.4305(2)
_cell_angle_alpha                98.0330(10)
_cell_angle_beta                 94.918(2)
_cell_angle_gamma                94.9710(10)
_cell_volume                     710.60(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    20024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.2850
_cell_measurement_theta_min      4.7090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23088
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.924
_diffrn_reflns_theta_min         4.759
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  -2.00   0.50    0.50    --  -38.50 125.00 -61.00  174
  2  ω   -102.00 -13.00   0.50    0.50    --  -38.50 145.00 105.00  178
  3  ω     34.00 113.00   0.50    0.50    --   49.56-145.00  53.00  158
  4  ω     94.00 176.00   0.50    0.50    --  111.00 125.00 -61.00  164
  5  ω     83.00 175.00   0.50    0.50    --  111.00 145.00 105.00  184
  6  ω     46.00 117.00   0.50    0.50    --  111.00-125.00-138.00  142
  7  ω    -44.00  -6.00   0.50    0.50    --   10.00 130.00 100.90   76
  8  ω    -33.00  -6.00   0.50    0.50    --   22.00 132.00-144.23   54
  9  ω      3.00  32.00   0.50    0.50    --   34.00  90.00 -73.24   58
 10  ω     10.00  36.00   0.50    0.50    --   38.00  85.00 -28.83   52
 11  ω     10.00  36.00   0.50    0.50    --   38.00  85.00 133.67   52
 12  ω     11.00  38.00   0.50    0.50    --   38.00  84.00   3.74   54
 13  ω     11.00  39.00   0.50    0.50    --   38.00  83.00-175.02   56
 14  ω   -105.00 -35.00   0.50    0.50    --  -38.50 -37.00  30.00  140
 15  ω    -42.00  28.00   0.50    0.50    --  -38.50  37.00 -30.00  140
 16  ω     18.00  45.00   0.50    0.50    --   42.00  78.00 118.67   54
 17  ω     17.00  45.00   0.50    0.50    --   42.00  80.00  63.19   56
 18  ω     24.00 101.00   0.50    0.50    --   49.56-125.00-138.00  154
 19  ω     26.00 114.00   0.50    0.50    --   49.56  77.00-120.00  176
 20  ω     26.00 114.00   0.50    0.50    --   49.56  77.00 150.00  176
 21  ω     26.00 114.00   0.50    0.50    --   49.56  77.00  90.00  176
 22  ω     31.00 119.00   0.50    0.50    --   54.00  77.00  50.03  176
 23  ω     31.00 118.00   0.50    0.50    --   54.00  76.00  -7.71  174
 24  ω     35.00 122.00   0.50    0.50    --   58.00  76.00-116.88  174
 25  ω     35.00 122.00   0.50    0.50    --   58.00  76.00  98.61  174
 26  ω     37.00 122.00   0.50    0.50    --   58.00  74.00 -69.90  170
 27  ω     41.00 121.00   0.50    0.50    --   58.00  68.00  65.36  160
 28  ω     35.00 122.00   0.50    0.50    --   58.00  76.00 151.89  174
 29  ω     35.00 122.00   0.50    0.50    --   58.00  76.00 -91.85  174
 30  ω     39.00 126.00   0.50    0.50    --   62.00  76.00-178.98  174
 31  ω     39.00 127.00   0.50    0.50    --   62.00  77.00 -36.38  176
 32  ω     45.00 125.00   0.50    0.50    --   62.00  67.00 -95.12  160
 33  ω     43.00 130.00   0.50    0.50    --   66.00  76.00 -50.64  174
 34  ω     50.00  95.00   0.50    0.50    --   70.00  76.00-165.32   90
 35  ω     60.00  86.00   0.50    0.50    --   74.00  69.00  93.19   52
 36  ω     61.00 100.00   0.50    0.50    --   78.00  67.00  35.32   78
 37  ω    113.00 139.00   0.50    0.50    --   78.00  67.00-138.79   52
 38  ω     61.00  93.00   0.50    0.50    --   78.00  67.00-138.79   64
 39  ω     61.00  87.00   0.50    0.50    --   82.00  76.00  98.29   52
 40  ω     68.00 101.00   0.50    0.50    --   82.00  63.00  13.18   66
 41  ω     72.00 111.00   0.50    0.50    --   86.00  65.00 -37.01   78
 42  ω     80.00 138.00   0.50    0.50    --   94.00  62.00 138.11  116
 43  ω     77.00 109.00   0.50    0.50    --   98.00  77.00  67.74   64
 44  ω    124.00 174.00   0.50    0.50    --  111.00  77.00-120.00  100
 45  ω     49.00  78.00   0.50    0.50    --  111.00 -77.00 -30.00   58
 46  ω     89.00 115.00   0.50    0.50    --  111.00  77.00-120.00   52
 47  ω     98.00 124.00   0.50    0.50    --  111.00  61.00-150.00   52
 48  ω     44.00  73.00   0.50    0.50    --  111.00-111.00 150.00   58
 49  ω    123.00 149.00   0.50    0.50    --  111.00  77.00  30.00   52
 50  ω    129.00 175.00   0.50    0.50    --  111.00  77.00 -30.00   92
 51  ω     87.00 112.00   0.50    0.50    --  111.00-111.00 -60.00   50
 52  ω     53.00  82.00   0.50    0.50    --  111.00-111.00 -60.00   58
 53  ω     48.00  99.00   0.50    0.50    --  111.00 -45.00 -60.00  102
 54  ω     79.00 113.00   0.50    0.50    --  111.00-111.00 150.00   68
 55  ω     89.00 115.00   0.50    0.50    --  111.00  77.00  30.00   52
 56  ω    132.00 166.00   0.50    0.50    --  111.00  61.00-150.00   68
 57  ω    146.00 176.00   0.50    0.50    --  111.00  77.00  90.00   60
 58  ω     94.00 134.00   0.50    0.50    --  111.00 -77.00 -30.00   80
 59  ω     88.00 126.00   0.50    0.50    --  111.00  77.00 150.00   76
 60  ω     88.00 122.00   0.50    0.50    --  111.00  77.00  90.00   68
 61  ω    131.00 160.00   0.50    0.50    --  111.00  77.00 -90.00   58
 62  ω     88.00 114.00   0.50    0.50    --  111.00  77.00 -30.00   52
 63  ω     89.00 130.00   0.50    0.50    --  111.00  77.00 120.00   82
 64  ω     90.00 138.00   0.50    0.50    --  111.00  77.00-180.00   96
 65  ω     88.00 114.00   0.50    0.50    --  111.00  77.00 -90.00   52
 66  ω    100.00 127.00   0.50    0.50    --  111.00  61.00-120.00   54
 67  ω     47.00  87.00   0.50    0.50    --  111.00 -94.00 -60.00   80
 68  ω    137.00 175.00   0.50    0.50    --  111.00  77.00-150.00   76
 69  ω     82.00 108.00   0.50    0.50    --  111.00 -15.00 150.00   52
 70  ω    100.00 126.00   0.50    0.50    --  111.00  61.00  90.00   52
 71  ω     89.00 115.00   0.50    0.50    --  111.00  77.00-150.00   52
 72  ω     88.00 114.00   0.50    0.50    --  111.00 -30.00 -30.00   52
 73  ω     98.00 133.00   0.50    0.50    --  111.00  61.00 -60.00   70
 74  ω     50.00  83.00   0.50    0.50    --  111.00 -30.00 -30.00   66
 75  ω     87.00 113.00   0.50    0.50    --  111.00-111.00-120.00   52
 76  ω     44.00  79.00   0.50    0.50    --  111.00-111.00-120.00   70
 77  ω     84.00 109.00   0.50    0.50    --  111.00 -94.00  30.00   50
 78  ω     78.00 108.00   0.50    0.50    --  111.00 -94.00-180.00   60
 79  ω     48.00  73.00   0.50    0.50    --  111.00 -94.00-180.00   50
 80  ω    146.00 172.00   0.50    0.50    --  111.00  15.00 120.00   52
 81  ω     81.00 114.00   0.50    0.50    --  111.00 -45.00 -30.00   66
 82  ω     88.00 123.00   0.50    0.50    --  111.00  77.00 -60.00   70
 83  ω    109.00 138.00   0.50    0.50    --  111.00  45.00-120.00   58
 84  ω    144.00 170.00   0.50    0.50    --  111.00  45.00-120.00   52
 85  ω     67.00 101.00   0.50    0.50    --  111.00 -94.00   0.00   68
 86  ω     95.00 133.00   0.50    0.50    --  111.00 -77.00-150.00   76
 87  ω    150.00 175.00   0.50    0.50    --  111.00  77.00  60.00   50
 88  ω     79.00 112.00   0.50    0.50    --  111.00-111.00-180.00   66
 89  ω     92.00 118.00   0.50    0.50    --  111.00  77.00  60.00   52
 90  ω     43.00  78.00   0.50    0.50    --  111.00 -15.00 150.00   70
 91  ω     52.00  77.00   0.50    0.50    --  111.00 -77.00-150.00   50
 92  ω     57.00 104.00   0.50    0.50    --  111.00 -77.00  90.00   94
 93  ω    104.00 131.00   0.50    0.50    --  111.00  15.00 120.00   54
 94  ω     98.00 135.00   0.50    0.50    --  111.00  61.00   0.00   74
 95  ω     84.00 113.00   0.50    0.50    --  111.00-111.00 -90.00   58
 96  ω    117.00 175.00   0.50    0.50    --  111.00  45.00 120.00  116
 97  ω     99.00 135.00   0.50    0.50    --  111.00  61.00  30.00   72
 98  ω     48.00  77.00   0.50    0.50    --  111.00 -15.00  60.00   58
 99  ω     87.00 114.00   0.50    0.50    --  111.00 -15.00  60.00   54
100  ω    128.00 172.00   0.50    0.50    --  111.00  61.00-180.00   88
101  ω     42.00  68.00   0.50    0.50    --  111.00-111.00 -90.00   52
102  ω    114.00 176.00   0.50    0.50    --  111.00  45.00  60.00  124
103  ω     58.00 144.00   0.50    0.50    --  111.00 178.00-120.00  172
104  ω     99.00 146.00   0.50    0.50    --  111.00  61.00 -90.00   94
105  ω     48.00  74.00   0.50    0.50    --  111.00 -81.00-128.54   52
106  ω     84.00 110.00   0.50    0.50    --  111.00 -81.00-128.54   52
107  ω    107.00 166.00   0.50    0.50    --  111.00  45.00-180.00  118
108  ω    126.00 151.00   0.50    0.50    --  111.00  45.00 -60.00   50
109  ω     89.00 143.00   0.50    0.50    --  111.00  77.00   0.00  108
110  ω     66.00 113.00   0.50    0.50    --  111.00-111.00 120.00   94
111  ω    117.00 163.00   0.50    0.50    --  111.00 102.00  78.43   92
112  ω    101.00 126.00   0.50    0.50    --  111.00  61.00-180.00   50
113  ω     52.00  78.00   0.50    0.50    --  111.00 -45.00 -30.00   52
114  ω     65.00  90.00   0.50    0.50    --  111.00-145.00  53.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0384707000
_diffrn_orient_matrix_UB_12      -0.1652662000
_diffrn_orient_matrix_UB_13      -0.0290349000
_diffrn_orient_matrix_UB_21      -0.0276496000
_diffrn_orient_matrix_UB_22      0.0057442000
_diffrn_orient_matrix_UB_23      -0.1626788000
_diffrn_orient_matrix_UB_31      0.1845035000
_diffrn_orient_matrix_UB_32      -0.0164450000
_diffrn_orient_matrix_UB_33      -0.0134562000
_diffrn_oxdiff_ac3_digest_frames 
;
01e4d20231d73648d14f586067648b505010126ebf0
;
_diffrn_oxdiff_ac3_digest_hkl    
;
013c2648a49b287c1d8da56cb3861be35ee6b5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.837
_reflns_number_gt                5351
_reflns_number_total             5644
_reflns_odcompleteness_completeness 97.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 2267 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5644
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.074
_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)+(0.1419P)²+0.0243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.1813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7AA(H7AA), C8AA(H8AA), C9(H9), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C5AA(H5AA), C6(H6), C5(H5), C4(H4), C4AA(H4AA), C3(H3), C2(H2), C1AA(H1AA),
 C3AA(H3AA), C2AA(H2AA)
2.c Idealised Me refined as rotating group:
 C0BA(H0BA,H0BB,H0BC), C9AA(H9AA,H9AB,H9AC), C2BA(H2BA,H2BB,H2BC), C10(H10A,
 H10B,H10C), C13(H13A,H13B,H13C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F3 F 0.7174(4) 0.0102(3) 0.4899(3) 0.0758(7) Uani 1 1 d . . . . .
F4 F 0.4677(4) 0.0393(3) 0.5672(3) 0.0867(9) Uani 1 1 d . . . . .
O2AA O 1.0046(3) 0.1249(3) 0.7265(4) 0.0697(7) Uani 1 1 d . . . . .
F1 F -0.1140(4) 0.5472(4) 0.0554(4) 0.0900(9) Uani 1 1 d . . . . .
N0AA N 0.6929(3) 0.2280(3) 0.6561(3) 0.0455(5) Uani 1 1 d . . . . .
O1 O 0.0260(5) 0.4127(3) 0.2091(4) 0.0755(8) Uani 1 1 d . . . . .
O0AA O 0.5742(4) 0.2008(3) 0.4201(3) 0.0714(8) Uani 1 1 d . . . . .
O1AA O 0.8368(5) -0.0396(3) 0.8048(4) 0.0736(8) Uani 1 1 d . . . . .
F2 F 0.1167(5) 0.4591(4) -0.0123(3) 0.0985(10) Uani 1 1 d . . . . .
O3 O 0.4058(4) 0.7621(4) -0.0197(3) 0.0732(8) Uani 1 1 d . . . . .
N1 N 0.1438(4) 0.6435(3) 0.1987(3) 0.0509(6) Uani 1 1 d . . . . .
C6AA C 0.7076(4) 0.3550(3) 0.6120(3) 0.0471(6) Uani 1 1 d . . . . .
C0AA C 0.6335(5) 0.3364(4) 0.4646(4) 0.0566(8) Uani 1 1 d . . . . .
C7AA C 0.7551(4) 0.2017(3) 0.7995(3) 0.0449(6) Uani 1 1 d . . . . .
H7AA H 0.823600 0.288730 0.847216 0.054 Uiso 1 1 calc R . . . .
C1BA C 0.8667(4) 0.0792(3) 0.7790(4) 0.0504(7) Uani 1 1 d . . . . .
C5AA C 0.7792(5) 0.4859(3) 0.6929(4) 0.0579(8) Uani 1 1 d . . . . .
H5AA H 0.817978 0.480627 0.787531 0.069 Uiso 1 1 calc R . . . .
C8AA C 0.6162(4) 0.1695(3) 0.8947(4) 0.0510(7) Uani 1 1 d . . . . .
H8AA H 0.554621 0.076484 0.854340 0.061 Uiso 1 1 calc R . . . .
C1 C 0.1026(5) 0.4696(4) 0.3358(4) 0.0564(7) Uani 1 1 d . . . . .
C12 C 0.3813(5) 0.7758(5) 0.1172(4) 0.0639(9) Uani 1 1 d . . . . .
C7 C 0.1809(4) 0.6133(3) 0.3308(3) 0.0470(6) Uani 1 1 d . . . . .
C9 C 0.1564(5) 0.9173(4) 0.2208(4) 0.0620(8) Uani 1 1 d . . . . .
H9 H 0.229261 0.937924 0.310890 0.074 Uiso 1 1 calc R . . . .
O2 O 0.4883(5) 0.7970(8) 0.2124(5) 0.1181(19) Uani 1 1 d . . . . .
C8 C 0.1952(4) 0.7729(4) 0.1382(3) 0.0540(7) Uani 1 1 d . . . . .
H8 H 0.135672 0.763021 0.042042 0.065 Uiso 1 1 calc R . . . .
C6 C 0.2787(5) 0.7016(4) 0.4463(4) 0.0544(7) Uani 1 1 d . . . . .
H6 H 0.328517 0.787772 0.425191 0.065 Uiso 1 1 calc R . . . .
C5 C 0.3098(5) 0.6767(5) 0.5860(4) 0.0638(9) Uani 1 1 d . . . . .
H5 H 0.375715 0.750512 0.646029 0.077 Uiso 1 1 calc R . . . .
C4 C 0.2591(6) 0.5592(6) 0.6526(5) 0.0719(11) Uani 1 1 d . . . . .
H4 H 0.289646 0.568218 0.751008 0.086 Uiso 1 1 calc R . . . .
C0BA C 0.6910(6) 0.1606(5) 1.0461(4) 0.0667(9) Uani 1 1 d . . . . .
H0BA H 0.775633 0.095733 1.041459 0.100 Uiso 1 1 calc GR . . . .
H0BB H 0.606362 0.125693 1.100973 0.100 Uiso 1 1 calc GR . . . .
H0BC H 0.738196 0.254627 1.091440 0.100 Uiso 1 1 calc GR . . . .
C9AA C 0.4975(7) 0.2865(6) 0.8989(6) 0.0762(12) Uani 1 1 d . . . . .
H9AA H 0.557660 0.378662 0.934484 0.114 Uiso 1 1 calc GR . . . .
H9AB H 0.413958 0.266725 0.961150 0.114 Uiso 1 1 calc GR . . . .
H9AC H 0.446298 0.287854 0.803591 0.114 Uiso 1 1 calc GR . . . .
C4AA C 0.8003(7) 0.6209(4) 0.6521(6) 0.0742(12) Uani 1 1 d . . . . .
H4AA H 0.851599 0.693342 0.723264 0.089 Uiso 1 1 calc R . . . .
C3 C 0.1698(6) 0.4325(6) 0.5912(5) 0.0746(11) Uani 1 1 d . . . . .
H3 H 0.152989 0.364163 0.652195 0.089 Uiso 1 1 calc R . . . .
C2 C 0.1007(6) 0.3920(4) 0.4489(5) 0.0682(10) Uani 1 1 d . . . . .
H2 H 0.045683 0.299629 0.427871 0.082 Uiso 1 1 calc R . . . .
B0AA B 0.6089(6) 0.1101(4) 0.5328(4) 0.0574(9) Uani 1 1 d . . . . .
C1AA C 0.6222(8) 0.4391(6) 0.3728(5) 0.0802(13) Uani 1 1 d . . . . .
H1AA H 0.570228 0.405863 0.281070 0.096 Uiso 1 1 calc R . . . .
B1 B 0.0391(7) 0.5147(6) 0.1040(5) 0.0694(11) Uani 1 1 d . . . . .
C3AA C 0.7566(8) 0.6650(5) 0.5212(7) 0.0852(16) Uani 1 1 d . . . . .
H3AA H 0.784597 0.761968 0.515938 0.102 Uiso 1 1 calc R . . . .
C2BA C 1.1155(7) 0.0172(8) 0.6883(8) 0.0922(16) Uani 1 1 d . . . . .
H2BA H 1.062980 -0.052318 0.609828 0.138 Uiso 1 1 calc GR . . . .
H2BB H 1.142290 -0.030325 0.769727 0.138 Uiso 1 1 calc GR . . . .
H2BC H 1.214888 0.062845 0.660051 0.138 Uiso 1 1 calc GR . . . .
C2AA C 0.6783(8) 0.5851(7) 0.3999(7) 0.0879(17) Uani 1 1 d . . . . .
H2AA H 0.659045 0.635514 0.323019 0.105 Uiso 1 1 calc R . . . .
C10 C 0.1911(9) 1.0392(6) 0.1327(8) 0.0914(16) Uani 1 1 d . . . . .
H10A H 0.302687 1.040503 0.107369 0.137 Uiso 1 1 calc GR . . . .
H10B H 0.176614 1.129800 0.188739 0.137 Uiso 1 1 calc GR . . . .
H10C H 0.115920 1.024035 0.046725 0.137 Uiso 1 1 calc GR . . . .
C13 C 0.5763(6) 0.7540(8) -0.0475(7) 0.0877(15) Uani 1 1 d . . . . .
H13A H 0.580898 0.704309 -0.142994 0.132 Uiso 1 1 calc GR . . . .
H13B H 0.630247 0.702563 0.021069 0.132 Uiso 1 1 calc GR . . . .
H13C H 0.631168 0.849679 -0.039162 0.132 Uiso 1 1 calc GR . . . .
C11 C -0.0182(8) 0.9105(6) 0.2567(8) 0.0903(16) Uani 1 1 d . . . . .
H11A H -0.091404 0.883774 0.170002 0.135 Uiso 1 1 calc GR . . . .
H11B H -0.040106 1.003323 0.303493 0.135 Uiso 1 1 calc GR . . . .
H11C H -0.035599 0.840152 0.319876 0.135 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 B0AA 1.389(5) . ?
F4 B0AA 1.367(5) . ?
O2AA C1BA 1.329(5) . ?
O2AA C2BA 1.445(6) . ?
F1 B1 1.367(7) . ?
N0AA C6AA 1.319(4) . ?
N0AA C7AA 1.464(4) . ?
N0AA B0AA 1.557(4) . ?
O1 C1 1.319(5) . ?
O1 B1 1.477(7) . ?
O0AA C0AA 1.322(5) . ?
O0AA B0AA 1.477(6) . ?
O1AA C1BA 1.186(4) . ?
F2 B1 1.377(6) . ?
O3 C12 1.313(5) . ?
O3 C13 1.444(6) . ?
N1 C7 1.332(4) . ?
N1 C8 1.459(5) . ?
N1 B1 1.544(5) . ?
C6AA C0AA 1.448(5) . ?
C6AA C5AA 1.406(5) . ?
C0AA C1AA 1.387(5) . ?
C7AA H7AA 0.9800 . ?
C7AA C1BA 1.531(5) . ?
C7AA C8AA 1.541(4) . ?
C5AA H5AA 0.9300 . ?
C5AA C4AA 1.380(5) . ?
C8AA H8AA 0.9800 . ?
C8AA C0BA 1.520(5) . ?
C8AA C9AA 1.527(6) . ?
C1 C7 1.453(5) . ?
C1 C2 1.375(6) . ?
C12 O2 1.180(6) . ?
C12 C8 1.547(6) . ?
C7 C6 1.413(4) . ?
C9 H9 0.9800 . ?
C9 C8 1.540(6) . ?
C9 C10 1.529(6) . ?
C9 C11 1.491(7) . ?
C8 H8 0.9800 . ?
C6 H6 0.9300 . ?
C6 C5 1.376(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.396(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.368(7) . ?
C0BA H0BA 0.9600 . ?
C0BA H0BB 0.9600 . ?
C0BA H0BC 0.9600 . ?
C9AA H9AA 0.9600 . ?
C9AA H9AB 0.9600 . ?
C9AA H9AC 0.9600 . ?
C4AA H4AA 0.9300 . ?
C4AA C3AA 1.384(8) . ?
C3 H3 0.9300 . ?
C3 C2 1.397(7) . ?
C2 H2 0.9300 . ?
C1AA H1AA 0.9300 . ?
C1AA C2AA 1.391(9) . ?
C3AA H3AA 0.9300 . ?
C3AA C2AA 1.354(10) . ?
C2BA H2BA 0.9600 . ?
C2BA H2BB 0.9600 . ?
C2BA H2BC 0.9600 . ?
C2AA H2AA 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1BA O2AA C2BA 116.3(4) . . ?
C6AA N0AA C7AA 124.2(3) . . ?
C6AA N0AA B0AA 110.6(3) . . ?
C7AA N0AA B0AA 125.1(3) . . ?
C1 O1 B1 111.2(3) . . ?
C0AA O0AA B0AA 110.9(3) . . ?
C12 O3 C13 114.4(4) . . ?
C7 N1 C8 128.7(3) . . ?
C7 N1 B1 110.7(3) . . ?
C8 N1 B1 120.5(3) . . ?
N0AA C6AA C0AA 107.6(3) . . ?
N0AA C6AA C5AA 126.7(3) . . ?
C5AA C6AA C0AA 125.8(3) . . ?
O0AA C0AA C6AA 111.0(3) . . ?
O0AA C0AA C1AA 120.6(4) . . ?
C1AA C0AA C6AA 128.4(4) . . ?
N0AA C7AA H7AA 107.9 . . ?
N0AA C7AA C1BA 107.4(2) . . ?
N0AA C7AA C8AA 113.0(3) . . ?
C1BA C7AA H7AA 107.9 . . ?
C1BA C7AA C8AA 112.4(2) . . ?
C8AA C7AA H7AA 107.9 . . ?
O2AA C1BA C7AA 109.9(3) . . ?
O1AA C1BA O2AA 124.1(3) . . ?
O1AA C1BA C7AA 126.0(3) . . ?
C6AA C5AA H5AA 115.4 . . ?
C4AA C5AA C6AA 129.2(4) . . ?
C4AA C5AA H5AA 115.4 . . ?
C7AA C8AA H8AA 108.9 . . ?
C0BA C8AA C7AA 109.6(3) . . ?
C0BA C8AA H8AA 108.9 . . ?
C0BA C8AA C9AA 110.0(3) . . ?
C9AA C8AA C7AA 110.5(3) . . ?
C9AA C8AA H8AA 108.9 . . ?
O1 C1 C7 110.7(3) . . ?
O1 C1 C2 119.8(4) . . ?
C2 C1 C7 129.5(4) . . ?
O3 C12 C8 111.5(3) . . ?
O2 C12 O3 124.2(4) . . ?
O2 C12 C8 124.1(4) . . ?
N1 C7 C1 107.3(3) . . ?
N1 C7 C6 127.5(3) . . ?
C6 C7 C1 125.2(3) . . ?
C8 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C10 C9 C8 110.2(4) . . ?
C11 C9 H9 108.3 . . ?
C11 C9 C8 111.5(4) . . ?
C11 C9 C10 110.2(4) . . ?
N1 C8 C12 109.1(3) . . ?
N1 C8 C9 116.2(3) . . ?
N1 C8 H8 106.7 . . ?
C12 C8 H8 106.7 . . ?
C9 C8 C12 110.8(3) . . ?
C9 C8 H8 106.7 . . ?
C7 C6 H6 115.7 . . ?
C5 C6 C7 128.5(3) . . ?
C5 C6 H6 115.7 . . ?
C6 C5 H5 114.6 . . ?
C6 C5 C4 130.8(4) . . ?
C4 C5 H5 114.6 . . ?
C5 C4 H4 116.0 . . ?
C3 C4 C5 128.1(4) . . ?
C3 C4 H4 116.0 . . ?
C8AA C0BA H0BA 109.5 . . ?
C8AA C0BA H0BB 109.5 . . ?
C8AA C0BA H0BC 109.5 . . ?
H0BA C0BA H0BB 109.5 . . ?
H0BA C0BA H0BC 109.5 . . ?
H0BB C0BA H0BC 109.5 . . ?
C8AA C9AA H9AA 109.5 . . ?
C8AA C9AA H9AB 109.5 . . ?
C8AA C9AA H9AC 109.5 . . ?
H9AA C9AA H9AB 109.5 . . ?
H9AA C9AA H9AC 109.5 . . ?
H9AB C9AA H9AC 109.5 . . ?
C5AA C4AA H4AA 115.1 . . ?
C5AA C4AA C3AA 129.8(5) . . ?
C3AA C4AA H4AA 115.1 . . ?
C4 C3 H3 115.7 . . ?
C4 C3 C2 128.6(4) . . ?
C2 C3 H3 115.7 . . ?
C1 C2 C3 129.0(4) . . ?
C1 C2 H2 115.5 . . ?
C3 C2 H2 115.5 . . ?
F3 B0AA N0AA 111.3(3) . . ?
F3 B0AA O0AA 111.0(3) . . ?
F4 B0AA F3 109.3(3) . . ?
F4 B0AA N0AA 113.4(3) . . ?
F4 B0AA O0AA 111.9(4) . . ?
O0AA B0AA N0AA 99.7(3) . . ?
C0AA C1AA H1AA 115.7 . . ?
C0AA C1AA C2AA 128.6(5) . . ?
C2AA C1AA H1AA 115.7 . . ?
F1 B1 O1 110.8(5) . . ?
F1 B1 F2 108.6(4) . . ?
F1 B1 N1 113.1(4) . . ?
O1 B1 N1 100.1(3) . . ?
F2 B1 O1 111.4(4) . . ?
F2 B1 N1 112.6(4) . . ?
C4AA C3AA H3AA 115.9 . . ?
C2AA C3AA C4AA 128.3(4) . . ?
C2AA C3AA H3AA 115.9 . . ?
O2AA C2BA H2BA 109.5 . . ?
O2AA C2BA H2BB 109.5 . . ?
O2AA C2BA H2BC 109.5 . . ?
H2BA C2BA H2BB 109.5 . . ?
H2BA C2BA H2BC 109.5 . . ?
H2BB C2BA H2BC 109.5 . . ?
C1AA C2AA H2AA 115.1 . . ?
C3AA C2AA C1AA 129.8(4) . . ?
C3AA C2AA H2AA 115.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_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 4.294
_oxdiff_exptl_absorpt_empirical_full_min 0.325
