# Electronic Supplementary Material (ESI) for ChemComm.
# 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_fanwx_190220_2
_database_code_depnum_ccdc_archive 'CCDC 1942792'
loop_
_audit_author_name
_audit_author_address
FanwxIF
;School of Pharmaceutical Sciences, Sun Yat sen University
China
;
_audit_update_record             
;
2019-07-24 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_audit_creation_date             2019-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
(E)-8-(2-fluoro-1-iodo-2-phenylvinyl)-4-methyldihydro-4l4,8l4-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborole-2,6(3H,5H)-dione
_chemical_formula_moiety         'C13 H12 B F I N O4'
_chemical_formula_sum            'C13 H12 B F I N O4'
_chemical_formula_weight         402.95
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
I I -0.3257 6.8362 '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'

_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           15
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   27.8895(3)
_cell_length_b                   6.86390(10)
_cell_length_c                   34.3921(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.2960(10)
_cell_angle_gamma                90
_cell_volume                     6350.48(13)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    19863
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.6890
_cell_measurement_theta_min      3.2730
_shelx_estimated_absorpt_T_max   0.296
_shelx_estimated_absorpt_T_min   0.086
_exptl_absorpt_coefficient_mu    16.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            31719
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.014
_diffrn_reflns_theta_min         2.664
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  28.00   0.50    0.05    --  -46.62  27.00 -49.00  178
  2  ω   -121.00 -32.00   0.50    0.05    --  -46.62 -27.00 148.00  178
  3  ω    -28.00  61.00   0.50    0.05    --   46.62 -27.00 148.00  178
  4  ω     33.00 122.00   0.50    0.05    --   46.62  27.00 -49.00  178
  5  ω   -175.00 -86.00   0.50    0.30    -- -100.00 -27.00 148.00  178
  6  ω   -114.00 -25.00   0.50    0.30    -- -100.00  27.00 -49.00  178
  7  ω     93.00 178.00   0.50    0.30    --  107.00  27.00 -49.00  170
  8  ω     32.00 121.00   0.50    0.30    --  107.00 -27.00 148.00  178
  9  ω     15.00  95.00   0.50    0.05    --   46.62-125.00-180.00  160
 10  ω     32.00 120.00   0.50    0.05    --   46.62  38.00 150.00  176
 11  ω   -124.00 -27.00   0.50    0.30    -- -100.00  77.00 -30.00  194
 12  ω     34.00 109.00   0.50    0.30    --  107.00 -94.00-150.00  150
 13  ω     34.00 109.00   0.50    0.30    --  107.00 -94.00 -60.00  150
 14  ω     34.00 109.00   0.50    0.30    --  107.00 -94.00 -30.00  150
 15  ω     92.00 178.00   0.50    0.30    --  107.00  30.00   0.00  172
 16  ω     34.00 109.00   0.50    0.30    --  107.00 -94.00 150.00  150
 17  ω     34.00 117.00   0.50    0.30    --  107.00-125.00 150.00  166
 18  ω     23.00  54.00   0.50    0.05    --   46.62  77.00  30.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0557285000
_diffrn_orient_matrix_UB_12      -0.0519007000
_diffrn_orient_matrix_UB_13      0.0123200000
_diffrn_orient_matrix_UB_21      -0.0042155000
_diffrn_orient_matrix_UB_22      -0.0612098000
_diffrn_orient_matrix_UB_23      0.0420708000
_diffrn_orient_matrix_UB_31      -0.0125094000
_diffrn_orient_matrix_UB_32      -0.2095380000
_diffrn_orient_matrix_UB_33      -0.0153471000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6226
_reflns_number_total             6495
_reflns_odcompleteness_completeness 99.92
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.846
_refine_diff_density_min         -1.264
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+34.5070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0844
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00H,H00I), C00K(H00A,H00B), C00O(H00J,H00K), C00T(H00F,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y), C010(H010),
 C011(H011), C012(H012), C013(H013), C014(H014)
2.c Idealised Me refined as rotating group:
 C00Q(H00C,H00D,H00E), C00S(H00L,H00M,H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I001 I 0.49595(2) 0.26351(3) 0.45759(2) 0.02077(7) Uani 1 1 d . . . . .
I002 I 0.36402(2) 0.71040(3) 0.71583(2) 0.02535(7) Uani 1 1 d . . . . .
F003 F 0.36939(7) 0.6267(3) 0.41167(6) 0.0275(4) Uani 1 1 d . . . . .
F004 F 0.39482(7) 0.1763(3) 0.66486(6) 0.0247(4) Uani 1 1 d . . . . .
O005 O 0.32080(8) 0.3308(3) 0.60663(6) 0.0177(4) Uani 1 1 d . . . . .
O006 O 0.35564(8) 0.4695(3) 0.47966(6) 0.0185(4) Uani 1 1 d . . . . .
O007 O 0.41038(8) 0.1964(3) 0.50294(7) 0.0206(5) Uani 1 1 d . . . . .
O008 O 0.27736(8) 0.5779(3) 0.46166(7) 0.0230(5) Uani 1 1 d . . . . .
O009 O 0.39468(8) -0.0803(4) 0.53185(7) 0.0240(5) Uani 1 1 d . . . . .
O00A O 0.28355(7) 0.6117(3) 0.62918(6) 0.0187(4) Uani 1 1 d . . . . .
O00B O 0.31281(9) 0.2289(3) 0.54353(7) 0.0228(5) Uani 1 1 d . . . . .
O00C O 0.24574(9) 0.8970(4) 0.61064(8) 0.0283(5) Uani 1 1 d . . . . .
N00D N 0.35495(9) 0.6549(4) 0.60265(7) 0.0155(5) Uani 1 1 d . . . . .
N00E N 0.34597(9) 0.1768(4) 0.43980(8) 0.0160(5) Uani 1 1 d . . . . .
C00F C 0.42734(11) 0.4111(5) 0.44687(9) 0.0181(6) Uani 1 1 d . . . . .
C00G C 0.41792(11) 0.5588(5) 0.42152(10) 0.0196(6) Uani 1 1 d . . . . .
C00H C 0.36290(11) 0.4750(5) 0.67604(9) 0.0170(6) Uani 1 1 d . . . . .
C00I C 0.32767(11) 0.8426(5) 0.60175(10) 0.0193(6) Uani 1 1 d . . . . .
H00H H 0.319871 0.899634 0.575009 0.023 Uiso 1 1 calc R . . . .
H00I H 0.347402 0.934721 0.620785 0.023 Uiso 1 1 calc R . . . .
C00J C 0.44660(12) 0.6715(5) 0.39875(10) 0.0195(6) Uani 1 1 d . . . . .
C00K C 0.30067(11) 0.3024(5) 0.42684(10) 0.0194(6) Uani 1 1 d . . . . .
H00A H 0.270948 0.228486 0.426607 0.023 Uiso 1 1 calc R . . . .
H00B H 0.297520 0.354701 0.400081 0.023 Uiso 1 1 calc R . . . .
C00L C 0.41466(12) 0.2623(5) 0.73341(10) 0.0191(6) Uani 1 1 d . . . . .
C00M C 0.30841(11) 0.4641(5) 0.45764(9) 0.0183(6) Uani 1 1 d . . . . .
C00N C 0.32391(11) 0.3539(5) 0.56879(9) 0.0176(6) Uani 1 1 d . . . . .
C00O C 0.34159(12) 0.5567(5) 0.56210(9) 0.0186(6) Uani 1 1 d . . . . .
H00J H 0.370341 0.549948 0.551277 0.022 Uiso 1 1 calc R . . . .
H00K H 0.315488 0.628304 0.543311 0.022 Uiso 1 1 calc R . . . .
C00P C 0.38938(11) 0.3192(5) 0.69138(9) 0.0182(6) Uani 1 1 d . . . . .
C00Q C 0.36130(12) 0.0908(5) 0.40502(10) 0.0218(6) Uani 1 1 d . . . . .
H00C H 0.336056 0.002569 0.390720 0.033 Uiso 1 1 calc GR . . . .
H00D H 0.392037 0.021599 0.414773 0.033 Uiso 1 1 calc GR . . . .
H00E H 0.365644 0.193044 0.387200 0.033 Uiso 1 1 calc GR . . . .
C00R C 0.52267(12) 0.8249(5) 0.39316(11) 0.0231(7) Uani 1 1 d . . . . .
H00R H 0.556044 0.854407 0.404191 0.028 Uiso 1 1 calc R . . . .
C00S C 0.40990(11) 0.6800(5) 0.61732(10) 0.0213(6) Uani 1 1 d . . . . .
H00L H 0.421297 0.761212 0.598850 0.032 Uiso 1 1 calc GR . . . .
H00M H 0.425769 0.555002 0.619088 0.032 Uiso 1 1 calc GR . . . .
H00N H 0.417998 0.740004 0.643456 0.032 Uiso 1 1 calc GR . . . .
C00T C 0.33965(11) 0.0210(5) 0.46872(9) 0.0205(6) Uani 1 1 d . . . . .
H00F H 0.338380 -0.106572 0.456380 0.025 Uiso 1 1 calc R . . . .
H00G H 0.309153 0.041353 0.476695 0.025 Uiso 1 1 calc R . . . .
C00U C 0.38747(13) 0.2396(5) 0.76166(11) 0.0264(7) Uani 1 1 d . . . . .
H00U H 0.353509 0.264963 0.754371 0.032 Uiso 1 1 calc R . . . .
C00V C 0.38423(11) 0.0364(5) 0.50486(9) 0.0188(6) Uani 1 1 d . . . . .
C00W C 0.49910(13) 0.8873(5) 0.35482(11) 0.0259(7) Uani 1 1 d . . . . .
H00W H 0.516714 0.957365 0.339992 0.031 Uiso 1 1 calc R . . . .
C00X C 0.49686(12) 0.7178(5) 0.41552(10) 0.0200(6) Uani 1 1 d . . . . .
H00X H 0.512884 0.677150 0.441492 0.024 Uiso 1 1 calc R . . . .
C00Y C 0.44906(13) 0.8461(5) 0.33821(10) 0.0259(7) Uani 1 1 d . . . . .
H00Y H 0.433104 0.890092 0.312469 0.031 Uiso 1 1 calc R . . . .
C00Z C 0.28049(12) 0.7901(5) 0.61342(10) 0.0197(6) Uani 1 1 d . . . . .
C010 C 0.48854(12) 0.1623(5) 0.78341(10) 0.0245(7) Uani 1 1 d . . . . .
H010 H 0.522524 0.137415 0.790825 0.029 Uiso 1 1 calc R . . . .
C011 C 0.46132(13) 0.1415(5) 0.81142(10) 0.0270(7) Uani 1 1 d . . . . .
H011 H 0.476927 0.102060 0.837566 0.032 Uiso 1 1 calc R . . . .
C012 C 0.46542(12) 0.2202(5) 0.74425(10) 0.0222(7) Uani 1 1 d . . . . .
H012 H 0.483711 0.230944 0.725313 0.027 Uiso 1 1 calc R . . . .
C013 C 0.42305(13) 0.7393(5) 0.36012(11) 0.0228(7) Uani 1 1 d . . . . .
H013 H 0.389545 0.712506 0.348995 0.027 Uiso 1 1 calc R . . . .
C014 C 0.41036(14) 0.1798(6) 0.80038(11) 0.0297(8) Uani 1 1 d . . . . .
H014 H 0.391888 0.164994 0.819094 0.036 Uiso 1 1 calc R . . . .
B015 B 0.33041(12) 0.5096(5) 0.63027(10) 0.0155(6) Uani 1 1 d . . . . .
B016 B 0.38773(12) 0.3219(5) 0.46847(11) 0.0162(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I001 C00F 2.110(3) . ?
I002 C00H 2.113(3) . ?
F003 C00G 1.387(3) . ?
F004 C00P 1.375(4) . ?
O005 C00N 1.336(4) . ?
O005 B015 1.458(4) . ?
O006 C00M 1.336(4) . ?
O006 B016 1.468(4) . ?
O007 C00V 1.330(4) . ?
O007 B016 1.466(4) . ?
O008 C00M 1.201(4) . ?
O009 C00V 1.202(4) . ?
O00A C00Z 1.333(4) . ?
O00A B015 1.475(4) . ?
O00B C00N 1.202(4) . ?
O00C C00Z 1.199(4) . ?
N00D C00I 1.493(4) . ?
N00D C00O 1.504(4) . ?
N00D C00S 1.492(4) . ?
N00D B015 1.646(4) . ?
N00E C00K 1.497(4) . ?
N00E C00Q 1.494(4) . ?
N00E C00T 1.502(4) . ?
N00E B016 1.648(4) . ?
C00F C00G 1.318(5) . ?
C00F B016 1.606(4) . ?
C00G C00J 1.477(4) . ?
C00H C00P 1.327(5) . ?
C00H B015 1.613(4) . ?
C00I H00H 0.9700 . ?
C00I H00I 0.9700 . ?
C00I C00Z 1.517(4) . ?
C00J C00X 1.404(5) . ?
C00J C013 1.398(5) . ?
C00K H00A 0.9700 . ?
C00K H00B 0.9700 . ?
C00K C00M 1.510(4) . ?
C00L C00P 1.483(4) . ?
C00L C00U 1.390(5) . ?
C00L C012 1.396(5) . ?
C00N C00O 1.515(4) . ?
C00O H00J 0.9700 . ?
C00O H00K 0.9700 . ?
C00Q H00C 0.9600 . ?
C00Q H00D 0.9600 . ?
C00Q H00E 0.9600 . ?
C00R H00R 0.9300 . ?
C00R C00W 1.377(5) . ?
C00R C00X 1.394(5) . ?
C00S H00L 0.9600 . ?
C00S H00M 0.9600 . ?
C00S H00N 0.9600 . ?
C00T H00F 0.9700 . ?
C00T H00G 0.9700 . ?
C00T C00V 1.512(4) . ?
C00U H00U 0.9300 . ?
C00U C014 1.379(5) . ?
C00W H00W 0.9300 . ?
C00W C00Y 1.390(5) . ?
C00X H00X 0.9300 . ?
C00Y H00Y 0.9300 . ?
C00Y C013 1.386(5) . ?
C010 H010 0.9300 . ?
C010 C011 1.382(5) . ?
C010 C012 1.389(5) . ?
C011 H011 0.9300 . ?
C011 C014 1.396(5) . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C014 H014 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
C00N O005 B015 113.2(2) . . ?
C00M O006 B016 114.2(2) . . ?
C00V O007 B016 113.6(2) . . ?
C00Z O00A B015 114.1(2) . . ?
C00I N00D C00O 111.5(2) . . ?
C00I N00D B015 104.3(2) . . ?
C00O N00D B015 103.0(2) . . ?
C00S N00D C00I 112.3(3) . . ?
C00S N00D C00O 110.3(2) . . ?
C00S N00D B015 114.9(2) . . ?
C00K N00E C00T 111.7(2) . . ?
C00K N00E B016 103.8(2) . . ?
C00Q N00E C00K 112.7(2) . . ?
C00Q N00E C00T 111.0(3) . . ?
C00Q N00E B016 114.3(2) . . ?
C00T N00E B016 102.8(2) . . ?
C00G C00F I001 119.9(2) . . ?
C00G C00F B016 123.9(3) . . ?
B016 C00F I001 116.0(2) . . ?
F003 C00G C00J 108.9(3) . . ?
C00F C00G F003 115.6(3) . . ?
C00F C00G C00J 135.4(3) . . ?
C00P C00H I002 116.5(2) . . ?
C00P C00H B015 128.1(3) . . ?
B015 C00H I002 115.3(2) . . ?
N00D C00I H00H 110.7 . . ?
N00D C00I H00I 110.7 . . ?
N00D C00I C00Z 105.2(3) . . ?
H00H C00I H00I 108.8 . . ?
C00Z C00I H00H 110.7 . . ?
C00Z C00I H00I 110.7 . . ?
C00X C00J C00G 121.5(3) . . ?
C013 C00J C00G 119.6(3) . . ?
C013 C00J C00X 118.9(3) . . ?
N00E C00K H00A 110.7 . . ?
N00E C00K H00B 110.7 . . ?
N00E C00K C00M 105.1(2) . . ?
H00A C00K H00B 108.8 . . ?
C00M C00K H00A 110.7 . . ?
C00M C00K H00B 110.7 . . ?
C00U C00L C00P 120.3(3) . . ?
C00U C00L C012 119.5(3) . . ?
C012 C00L C00P 120.2(3) . . ?
O006 C00M C00K 110.8(3) . . ?
O008 C00M O006 123.4(3) . . ?
O008 C00M C00K 125.8(3) . . ?
O005 C00N C00O 111.4(3) . . ?
O00B C00N O005 123.3(3) . . ?
O00B C00N C00O 125.3(3) . . ?
N00D C00O C00N 106.4(2) . . ?
N00D C00O H00J 110.5 . . ?
N00D C00O H00K 110.5 . . ?
C00N C00O H00J 110.5 . . ?
C00N C00O H00K 110.5 . . ?
H00J C00O H00K 108.6 . . ?
F004 C00P C00L 110.6(3) . . ?
C00H C00P F004 117.3(3) . . ?
C00H C00P C00L 132.1(3) . . ?
N00E C00Q H00C 109.5 . . ?
N00E C00Q H00D 109.5 . . ?
N00E C00Q H00E 109.5 . . ?
H00C C00Q H00D 109.5 . . ?
H00C C00Q H00E 109.5 . . ?
H00D C00Q H00E 109.5 . . ?
C00W C00R H00R 119.8 . . ?
C00W C00R C00X 120.4(3) . . ?
C00X C00R H00R 119.8 . . ?
N00D C00S H00L 109.5 . . ?
N00D C00S H00M 109.5 . . ?
N00D C00S H00N 109.5 . . ?
H00L C00S H00M 109.5 . . ?
H00L C00S H00N 109.5 . . ?
H00M C00S H00N 109.5 . . ?
N00E C00T H00F 110.5 . . ?
N00E C00T H00G 110.5 . . ?
N00E C00T C00V 106.3(2) . . ?
H00F C00T H00G 108.7 . . ?
C00V C00T H00F 110.5 . . ?
C00V C00T H00G 110.5 . . ?
C00L C00U H00U 119.7 . . ?
C014 C00U C00L 120.6(3) . . ?
C014 C00U H00U 119.7 . . ?
O007 C00V C00T 111.1(3) . . ?
O009 C00V O007 124.4(3) . . ?
O009 C00V C00T 124.6(3) . . ?
C00R C00W H00W 119.9 . . ?
C00R C00W C00Y 120.3(3) . . ?
C00Y C00W H00W 119.9 . . ?
C00J C00X H00X 120.1 . . ?
C00R C00X C00J 119.9(3) . . ?
C00R C00X H00X 120.1 . . ?
C00W C00Y H00Y 120.1 . . ?
C013 C00Y C00W 119.8(3) . . ?
C013 C00Y H00Y 120.1 . . ?
O00A C00Z C00I 111.0(3) . . ?
O00C C00Z O00A 124.0(3) . . ?
O00C C00Z C00I 124.9(3) . . ?
C011 C010 H010 119.8 . . ?
C011 C010 C012 120.4(3) . . ?
C012 C010 H010 119.8 . . ?
C010 C011 H011 120.1 . . ?
C010 C011 C014 119.9(3) . . ?
C014 C011 H011 120.1 . . ?
C00L C012 H012 120.1 . . ?
C010 C012 C00L 119.8(3) . . ?
C010 C012 H012 120.1 . . ?
C00J C013 H013 119.6 . . ?
C00Y C013 C00J 120.7(3) . . ?
C00Y C013 H013 119.6 . . ?
C00U C014 C011 119.8(3) . . ?
C00U C014 H014 120.1 . . ?
C011 C014 H014 120.1 . . ?
O005 B015 O00A 110.8(2) . . ?
O005 B015 N00D 103.4(2) . . ?
O005 B015 C00H 113.2(3) . . ?
O00A B015 N00D 101.4(2) . . ?
O00A B015 C00H 111.1(2) . . ?
C00H B015 N00D 116.1(2) . . ?
O006 B016 N00E 101.0(2) . . ?
O006 B016 C00F 113.6(3) . . ?
O007 B016 O006 110.8(3) . . ?
O007 B016 N00E 102.4(2) . . ?
O007 B016 C00F 113.3(2) . . ?
C00F B016 N00E 114.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I001 C00F C00G F003 170.4(2) . . . . ?
I001 C00F C00G C00J -6.9(5) . . . . ?
I001 C00F B016 O006 147.9(2) . . . . ?
I001 C00F B016 O007 20.3(3) . . . . ?
I001 C00F B016 N00E -96.8(3) . . . . ?
I002 C00H C00P F004 -171.06(19) . . . . ?
I002 C00H C00P C00L 10.6(5) . . . . ?
I002 C00H B015 O005 -166.01(19) . . . . ?
I002 C00H B015 O00A -40.6(3) . . . . ?
I002 C00H B015 N00D 74.6(3) . . . . ?
F003 C00G C00J C00X 144.8(3) . . . . ?
F003 C00G C00J C013 -33.2(4) . . . . ?
O005 C00N C00O N00D 6.1(3) . . . . ?
O00B C00N C00O N00D -175.4(3) . . . . ?
N00D C00I C00Z O00A 14.1(3) . . . . ?
N00D C00I C00Z O00C -169.0(3) . . . . ?
N00E C00K C00M O006 14.3(3) . . . . ?
N00E C00K C00M O008 -167.7(3) . . . . ?
N00E C00T C00V O007 9.6(3) . . . . ?
N00E C00T C00V O009 -170.5(3) . . . . ?
C00F C00G C00J C00X -37.8(6) . . . . ?
C00F C00G C00J C013 144.3(4) . . . . ?
C00G C00F B016 O006 -36.8(4) . . . . ?
C00G C00F B016 O007 -164.4(3) . . . . ?
C00G C00F B016 N00E 78.6(4) . . . . ?
C00G C00J C00X C00R -179.8(3) . . . . ?
C00G C00J C013 C00Y 179.7(3) . . . . ?
C00I N00D C00O C00N -124.7(3) . . . . ?
C00I N00D B015 O005 132.8(2) . . . . ?
C00I N00D B015 O00A 18.0(3) . . . . ?
C00I N00D B015 C00H -102.6(3) . . . . ?
C00K N00E C00T C00V -127.9(3) . . . . ?
C00K N00E B016 O006 21.2(3) . . . . ?
C00K N00E B016 O007 135.6(2) . . . . ?
C00K N00E B016 C00F -101.3(3) . . . . ?
C00L C00U C014 C011 0.0(6) . . . . ?
C00M O006 B016 O007 -121.6(3) . . . . ?
C00M O006 B016 N00E -13.7(3) . . . . ?
C00M O006 B016 C00F 109.6(3) . . . . ?
C00N O005 B015 O00A 94.3(3) . . . . ?
C00N O005 B015 N00D -13.7(3) . . . . ?
C00N O005 B015 C00H -140.1(3) . . . . ?
C00O N00D C00I C00Z 91.4(3) . . . . ?
C00O N00D B015 O005 16.2(3) . . . . ?
C00O N00D B015 O00A -98.6(2) . . . . ?
C00O N00D B015 C00H 140.7(3) . . . . ?
C00P C00H B015 O005 15.2(4) . . . . ?
C00P C00H B015 O00A 140.5(3) . . . . ?
C00P C00H B015 N00D -104.2(4) . . . . ?
C00P C00L C00U C014 177.6(3) . . . . ?
C00P C00L C012 C010 -178.4(3) . . . . ?
C00Q N00E C00K C00M -145.4(3) . . . . ?
C00Q N00E C00T C00V 105.4(3) . . . . ?
C00Q N00E B016 O006 144.3(3) . . . . ?
C00Q N00E B016 O007 -101.3(3) . . . . ?
C00Q N00E B016 C00F 21.9(4) . . . . ?
C00R C00W C00Y C013 -0.9(5) . . . . ?
C00S N00D C00I C00Z -144.2(3) . . . . ?
C00S N00D C00O C00N 109.7(3) . . . . ?
C00S N00D B015 O005 -103.8(3) . . . . ?
C00S N00D B015 O00A 141.4(3) . . . . ?
C00S N00D B015 C00H 20.8(4) . . . . ?
C00T N00E C00K C00M 88.8(3) . . . . ?
C00T N00E B016 O006 -95.3(3) . . . . ?
C00T N00E B016 O007 19.1(3) . . . . ?
C00T N00E B016 C00F 142.2(3) . . . . ?
C00U C00L C00P F004 -118.2(3) . . . . ?
C00U C00L C00P C00H 60.2(5) . . . . ?
C00U C00L C012 C010 -2.1(5) . . . . ?
C00V O007 B016 O006 92.3(3) . . . . ?
C00V O007 B016 N00E -14.7(3) . . . . ?
C00V O007 B016 C00F -138.7(3) . . . . ?
C00W C00R C00X C00J 0.6(5) . . . . ?
C00W C00Y C013 C00J -0.3(5) . . . . ?
C00X C00J C013 C00Y 1.7(5) . . . . ?
C00X C00R C00W C00Y 0.8(5) . . . . ?
C00Z O00A B015 O005 -119.4(3) . . . . ?
C00Z O00A B015 N00D -10.2(3) . . . . ?
C00Z O00A B015 C00H 113.8(3) . . . . ?
C010 C011 C014 C00U -0.5(6) . . . . ?
C011 C010 C012 C00L 1.6(5) . . . . ?
C012 C00L C00P F004 58.0(4) . . . . ?
C012 C00L C00P C00H -123.6(4) . . . . ?
C012 C00L C00U C014 1.3(5) . . . . ?
C012 C010 C011 C014 -0.3(6) . . . . ?
C013 C00J C00X C00R -1.9(5) . . . . ?
B015 O005 C00N O00B -172.9(3) . . . . ?
B015 O005 C00N C00O 5.5(3) . . . . ?
B015 O00A C00Z O00C -178.6(3) . . . . ?
B015 O00A C00Z C00I -1.6(4) . . . . ?
B015 N00D C00I C00Z -19.1(3) . . . . ?
B015 N00D C00O C00N -13.4(3) . . . . ?
B015 C00H C00P F004 7.8(5) . . . . ?
B015 C00H C00P C00L -170.5(3) . . . . ?
B016 O006 C00M O008 -177.4(3) . . . . ?
B016 O006 C00M C00K 0.6(4) . . . . ?
B016 O007 C00V O009 -175.7(3) . . . . ?
B016 O007 C00V C00T 4.2(4) . . . . ?
B016 N00E C00K C00M -21.2(3) . . . . ?
B016 N00E C00T C00V -17.2(3) . . . . ?
B016 C00F C00G F003 -4.8(5) . . . . ?
B016 C00F C00G C00J 177.9(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.250 -0.444 0.750 241.9 58.9 ?
2 0.250 -0.309 0.250 241.9 58.9 ?
3 0.250 0.583 0.000 10.4 0.0 ?
4 0.250 0.917 0.500 10.4 0.0 ?
5 0.750 -0.387 0.750 241.9 58.9 ?
6 0.750 0.055 0.250 241.9 58.9 ?
7 0.750 0.083 0.500 10.4 0.0 ?
8 0.750 0.417 0.000 10.4 0.0 ?

_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 9.583
_oxdiff_exptl_absorpt_empirical_full_min 0.652
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_fanwx_190923
_database_code_depnum_ccdc_archive 'CCDC 1956650'
loop_
_audit_author_name
_audit_author_address
FanwxalkylIFII
;School of Pharmaceutical Sciences, Sun Yat sen University
China
;
_audit_update_record             
;
2019-09-30 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_audit_creation_date             2019-09-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 B F I N O4'
_chemical_formula_sum            'C13 H14 B F I N O4'
_chemical_formula_weight         404.96
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
I I -0.3257 6.8362 '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'

_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      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_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.6367(3)
_cell_length_b                   14.4997(3)
_cell_length_c                   15.6349(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2864.76(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5037
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.7760
_cell_measurement_theta_min      5.4280
_shelx_estimated_absorpt_T_max   0.269
_shelx_estimated_absorpt_T_min   0.125
_exptl_absorpt_coefficient_mu    17.818
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9854
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.160
_diffrn_reflns_theta_min         5.438
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00  93.00   0.50    0.05    --   46.37  75.00   0.00  126
  2  ω   -142.00-101.00   0.50    0.20    -- -100.00 -49.00  18.00   82
  3  ω   -118.00 -86.00   0.50    0.20    -- -100.00  75.00   0.00   64
  4  ω     74.00 100.00   0.50    0.20    --  105.44-110.00 150.00   52
  5  ω   -118.00 -72.00   0.50    0.05    --  -46.37-125.00  30.00   92
  6  ω     16.00  91.00   0.50    0.05    --   46.37-125.00 -90.00  150
  7  ω     40.00  69.00   0.50    0.05    --   46.37-125.00-150.00   58
  8  ω    -83.00 -33.00   0.50    0.20    -- -100.00  75.00   0.00  100
  9  ω     42.00 108.00   0.50    0.20    --  105.44 -94.00-180.00  132
 10  ω     52.00 105.00   0.50    0.20    --  105.44 -94.00  30.00  106
 11  ω     57.00 123.00   0.50    0.20    --  105.44 -61.00   0.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0021491000
_diffrn_orient_matrix_UB_12      -0.0988709000
_diffrn_orient_matrix_UB_13      0.0361006000
_diffrn_orient_matrix_UB_21      -0.0733895000
_diffrn_orient_matrix_UB_22      -0.0322084000
_diffrn_orient_matrix_UB_23      -0.0727763000
_diffrn_orient_matrix_UB_31      0.0972645000
_diffrn_orient_matrix_UB_32      -0.0219916000
_diffrn_orient_matrix_UB_33      -0.0557667000
_diffrn_oxdiff_digest_frames     
;
016c582635d53b032b8c86cb87e0979b6600120e318
;
_diffrn_oxdiff_digest_hkl        
;
0188f8b3b1e235deb7134d849223ce6f744f63
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2519
_reflns_number_total             2867
_reflns_odcompleteness_completeness 99.72
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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         1.836
_refine_diff_density_min         -3.037
_refine_diff_density_rms         0.278
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0631
_refine_ls_restrained_S_all      1.117
_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)+(0.1372P)²+2.4582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.1931
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00J(H00K,H00L), C00K(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00G(H00H), C00H(H00I), C00I(H00J)
2.d Idealised Me refined as rotating group:
 C00F(H00D,H00F,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I001 I 0.02486(3) 0.64642(3) 0.55265(2) 0.0223(2) Uani 1 1 d . . . . .
F002 F 0.1670(3) 0.6235(3) 0.7289(2) 0.0317(8) Uani 1 1 d . . . . .
O003 O 0.2466(3) 0.5202(3) 0.5750(2) 0.0229(8) Uani 1 1 d . . . . .
O004 O 0.3747(3) 0.6428(3) 0.5888(3) 0.0223(9) Uani 1 1 d . . . . .
O005 O 0.2003(3) 0.3890(3) 0.5106(3) 0.0267(8) Uani 1 1 d . . . . .
O006 O 0.5450(4) 0.6207(5) 0.5504(3) 0.0350(11) Uani 1 1 d . . . . .
N007 N 0.2886(4) 0.6122(4) 0.4518(3) 0.0204(10) Uani 1 1 d . . . . .
C008 C 0.2257(4) 0.4694(4) 0.5075(4) 0.0231(11) Uani 1 1 d . . . . .
C009 C 0.1131(4) 0.7815(4) 0.7181(3) 0.0216(11) Uani 1 1 d . . . . .
C00A C 0.1824(4) 0.6905(4) 0.5899(3) 0.0207(10) Uani 1 1 d . . . . .
H00A H 0.196099 0.749676 0.561704 0.025 Uiso 1 1 calc R . . . .
C00B C 0.1863(4) 0.7072(4) 0.6861(3) 0.0222(11) Uani 1 1 d . . . . .
H00B H 0.258591 0.726209 0.700165 0.027 Uiso 1 1 calc R . . . .
C00C C 0.1355(5) 0.8725(4) 0.6980(4) 0.0248(12) Uani 1 1 d . . . . .
H00C H 0.193483 0.885657 0.663500 0.030 Uiso 1 1 calc R . . . .
C00D C 0.4520(5) 0.6233(5) 0.5328(4) 0.0254(12) Uani 1 1 d . . . . .
C00E C -0.0131(5) 0.9260(6) 0.7809(4) 0.0325(15) Uani 1 1 d . . . . .
H00E H -0.054739 0.973766 0.801793 0.039 Uiso 1 1 calc R . . . .
C00F C 0.2539(5) 0.6948(4) 0.4008(3) 0.0260(12) Uani 1 1 d . . . . .
H00D H 0.274846 0.687129 0.342201 0.039 Uiso 1 1 calc GR . . . .
H00F H 0.286323 0.749338 0.423682 0.039 Uiso 1 1 calc GR . . . .
H00G H 0.178305 0.700625 0.403914 0.039 Uiso 1 1 calc GR . . . .
C00G C 0.0735(5) 0.9446(4) 0.7283(4) 0.0272(12) Uani 1 1 d . . . . .
H00H H 0.089630 1.005123 0.713527 0.033 Uiso 1 1 calc R . . . .
C00H C -0.0365(5) 0.8333(6) 0.8019(4) 0.0283(13) Uani 1 1 d . . . . .
H00I H -0.093696 0.820079 0.837285 0.034 Uiso 1 1 calc R . . . .
C00I C 0.0255(4) 0.7619(5) 0.7700(4) 0.0272(14) Uani 1 1 d . . . . .
H00J H 0.008798 0.701049 0.783062 0.033 Uiso 1 1 calc R . . . .
C00J C 0.2338(5) 0.5259(5) 0.4262(4) 0.0269(12) Uani 1 1 d . . . . .
H00K H 0.274288 0.493150 0.383152 0.032 Uiso 1 1 calc R . . . .
H00L H 0.164079 0.539298 0.403518 0.032 Uiso 1 1 calc R . . . .
C00K C 0.4072(5) 0.6020(5) 0.4460(3) 0.0249(12) Uani 1 1 d . . . . .
H00M H 0.425549 0.539603 0.429210 0.030 Uiso 1 1 calc R . . . .
H00N H 0.435483 0.644307 0.403747 0.030 Uiso 1 1 calc R . . . .
B00L B 0.2694(5) 0.6190(5) 0.5565(4) 0.0192(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I001 C00A 2.170(5) . ?
F002 C00B 1.407(7) . ?
O003 C008 1.314(7) . ?
O003 B00L 1.489(9) . ?
O004 C00D 1.342(7) . ?
O004 B00L 1.463(8) . ?
O005 C008 1.210(7) . ?
O006 C00D 1.208(8) . ?
N007 C00F 1.505(7) . ?
N007 C00J 1.485(8) . ?
N007 C00K 1.508(8) . ?
N007 B00L 1.657(7) . ?
C008 C00J 1.516(9) . ?
C009 C00B 1.506(8) . ?
C009 C00C 1.386(8) . ?
C009 C00I 1.401(8) . ?
C00A H00A 0.9800 . ?
C00A C00B 1.524(7) . ?
C00A B00L 1.599(9) . ?
C00B H00B 0.9800 . ?
C00C H00C 0.9300 . ?
C00C C00G 1.390(8) . ?
C00D C00K 1.502(8) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.394(9) . ?
C00E C00H 1.414(11) . ?
C00F H00D 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00G H00H 0.9300 . ?
C00H H00I 0.9300 . ?
C00H C00I 1.392(9) . ?
C00I H00J 0.9300 . ?
C00J H00K 0.9700 . ?
C00J H00L 0.9700 . ?
C00K H00M 0.9700 . ?
C00K H00N 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 O003 B00L 115.0(4) . . ?
C00D O004 B00L 112.7(4) . . ?
C00F N007 C00K 109.6(5) . . ?
C00F N007 B00L 115.7(5) . . ?
C00J N007 C00F 113.1(4) . . ?
C00J N007 C00K 111.4(5) . . ?
C00J N007 B00L 104.4(5) . . ?
C00K N007 B00L 102.2(4) . . ?
O003 C008 C00J 110.9(5) . . ?
O005 C008 O003 124.2(5) . . ?
O005 C008 C00J 124.9(5) . . ?
C00C C009 C00B 118.7(5) . . ?
C00C C009 C00I 119.0(6) . . ?
C00I C009 C00B 122.2(5) . . ?
I001 C00A H00A 107.4 . . ?
C00B C00A I001 109.9(3) . . ?
C00B C00A H00A 107.4 . . ?
C00B C00A B00L 113.8(4) . . ?
B00L C00A I001 110.6(4) . . ?
B00L C00A H00A 107.4 . . ?
F002 C00B C009 110.6(4) . . ?
F002 C00B C00A 109.1(5) . . ?
F002 C00B H00B 107.2 . . ?
C009 C00B C00A 115.0(4) . . ?
C009 C00B H00B 107.2 . . ?
C00A C00B H00B 107.2 . . ?
C009 C00C H00C 119.2 . . ?
C009 C00C C00G 121.6(5) . . ?
C00G C00C H00C 119.2 . . ?
O004 C00D C00K 111.0(5) . . ?
O006 C00D O004 124.4(6) . . ?
O006 C00D C00K 124.5(6) . . ?
C00G C00E H00E 120.5 . . ?
C00G C00E C00H 119.1(6) . . ?
C00H C00E H00E 120.5 . . ?
N007 C00F H00D 109.5 . . ?
N007 C00F H00F 109.5 . . ?
N007 C00F H00G 109.5 . . ?
H00D C00F H00F 109.5 . . ?
H00D C00F H00G 109.5 . . ?
H00F C00F H00G 109.5 . . ?
C00C C00G C00E 119.8(6) . . ?
C00C C00G H00H 120.1 . . ?
C00E C00G H00H 120.1 . . ?
C00E C00H H00I 119.8 . . ?
C00I C00H C00E 120.3(6) . . ?
C00I C00H H00I 119.8 . . ?
C009 C00I H00J 119.9 . . ?
C00H C00I C009 120.1(6) . . ?
C00H C00I H00J 119.9 . . ?
N007 C00J C008 105.1(5) . . ?
N007 C00J H00K 110.7 . . ?
N007 C00J H00L 110.7 . . ?
C008 C00J H00K 110.7 . . ?
C008 C00J H00L 110.7 . . ?
H00K C00J H00L 108.8 . . ?
N007 C00K H00M 110.2 . . ?
N007 C00K H00N 110.2 . . ?
C00D C00K N007 107.4(4) . . ?
C00D C00K H00M 110.2 . . ?
C00D C00K H00N 110.2 . . ?
H00M C00K H00N 108.5 . . ?
O003 B00L N007 99.4(5) . . ?
O003 B00L C00A 115.2(5) . . ?
O004 B00L O003 109.6(5) . . ?
O004 B00L N007 102.8(5) . . ?
O004 B00L C00A 111.1(5) . . ?
C00A B00L N007 117.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I001 C00A C00B F002 63.5(5) . . . . ?
I001 C00A C00B C009 -61.5(5) . . . . ?
I001 C00A B00L O003 -48.7(5) . . . . ?
I001 C00A B00L O004 -174.1(4) . . . . ?
I001 C00A B00L N007 68.0(6) . . . . ?
O003 C008 C00J N007 13.8(6) . . . . ?
O004 C00D C00K N007 1.2(8) . . . . ?
O005 C008 C00J N007 -168.2(5) . . . . ?
O006 C00D C00K N007 179.3(7) . . . . ?
C008 O003 B00L O004 -121.8(5) . . . . ?
C008 O003 B00L N007 -14.5(6) . . . . ?
C008 O003 B00L C00A 112.0(5) . . . . ?
C009 C00C C00G C00E 0.7(9) . . . . ?
C00B C009 C00C C00G -177.5(5) . . . . ?
C00B C009 C00I C00H 176.4(5) . . . . ?
C00B C00A B00L O003 75.6(6) . . . . ?
C00B C00A B00L O004 -49.8(7) . . . . ?
C00B C00A B00L N007 -167.7(5) . . . . ?
C00C C009 C00B F002 165.5(5) . . . . ?
C00C C009 C00B C00A -70.3(6) . . . . ?
C00C C009 C00I C00H -1.2(8) . . . . ?
C00D O004 B00L O003 85.8(6) . . . . ?
C00D O004 B00L N007 -19.2(7) . . . . ?
C00D O004 B00L C00A -145.8(5) . . . . ?
C00E C00H C00I C009 1.3(9) . . . . ?
C00F N007 C00J C008 -148.0(4) . . . . ?
C00F N007 C00K C00D 111.2(5) . . . . ?
C00F N007 B00L O003 146.5(5) . . . . ?
C00F N007 B00L O004 -100.8(6) . . . . ?
C00F N007 B00L C00A 21.5(7) . . . . ?
C00G C00E C00H C00I -0.5(9) . . . . ?
C00H C00E C00G C00C -0.5(9) . . . . ?
C00I C009 C00B F002 -12.1(7) . . . . ?
C00I C009 C00B C00A 112.1(6) . . . . ?
C00I C009 C00C C00G 0.2(8) . . . . ?
C00J N007 C00K C00D -123.0(5) . . . . ?
C00J N007 B00L O003 21.6(5) . . . . ?
C00J N007 B00L O004 134.3(5) . . . . ?
C00J N007 B00L C00A -103.4(6) . . . . ?
C00K N007 C00J C008 88.1(5) . . . . ?
C00K N007 B00L O003 -94.5(5) . . . . ?
C00K N007 B00L O004 18.2(6) . . . . ?
C00K N007 B00L C00A 140.5(6) . . . . ?
B00L O003 C008 O005 -176.3(5) . . . . ?
B00L O003 C008 C00J 1.7(6) . . . . ?
B00L O004 C00D O006 -165.7(7) . . . . ?
B00L O004 C00D C00K 12.4(8) . . . . ?
B00L N007 C00J C008 -21.4(6) . . . . ?
B00L N007 C00K C00D -12.0(7) . . . . ?
B00L C00A C00B F002 -61.2(6) . . . . ?
B00L C00A C00B C009 173.8(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 7.917
_oxdiff_exptl_absorpt_empirical_full_min 0.372
####################################################################### 
# 
# 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_fanwx_190911_2
_database_code_depnum_ccdc_archive 'CCDC 1953148'
loop_
_audit_author_name
_audit_author_address
FanwxalkylIF
;School of Pharmaceutical Sciences, Sun Yat sen University
China
;
_audit_update_record             
;
2019-09-12 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 B F I N O4'
_chemical_formula_weight         418.99

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'
I I -0.3257 6.8362 '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'
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'

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

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

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

_cell_length_a                   12.7883(2)
_cell_length_b                   11.1705(2)
_cell_length_c                   10.9261(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.020(2)
_cell_angle_gamma                90
_cell_volume                     1526.59(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    16.743
_shelx_estimated_absorpt_T_min   0.082
_shelx_estimated_absorpt_T_max   0.285
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29253
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.534
_diffrn_reflns_theta_max         77.051
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3120
_reflns_number_gt                2947
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+2.2005P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00058(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3120
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I12 I 0.73640(2) 0.72656(2) 0.13728(2) 0.02809(11) Uani 1 1 d . . . . .
F11 F 0.81264(16) 0.4089(2) 0.3559(2) 0.0366(5) Uani 1 1 d . . . . .
O8 O 0.61257(17) 0.5658(2) 0.37132(19) 0.0209(4) Uani 1 1 d . . . . .
O2 O 0.52451(17) 0.5826(2) 0.1532(2) 0.0233(4) Uani 1 1 d . . . . .
O14 O 0.62019(18) 0.4887(2) 0.56269(19) 0.0252(5) Uani 1 1 d . . . . .
O13 O 0.34880(18) 0.5590(2) 0.0801(2) 0.0274(5) Uani 1 1 d . . . . .
N5 N 0.5688(2) 0.3868(2) 0.2474(2) 0.0200(5) Uani 1 1 d . . . . .
C7 C 0.6096(2) 0.4762(3) 0.4511(3) 0.0211(6) Uani 1 1 d . . . . .
C9 C 0.7275(3) 0.5449(3) 0.2057(3) 0.0226(6) Uani 1 1 d . . . . .
H9 H 0.734767 0.488146 0.139524 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5907(3) 0.3575(3) 0.3839(3) 0.0223(6) Uani 1 1 d . . . . .
H6A H 0.653216 0.306679 0.406183 0.027 Uiso 1 1 calc R U . . .
H6B H 0.530068 0.316523 0.405331 0.027 Uiso 1 1 calc R U . . .
C3 C 0.4333(3) 0.5205(3) 0.1361(3) 0.0222(6) Uani 1 1 d . . . . .
C4 C 0.4510(3) 0.3992(3) 0.1954(3) 0.0252(7) Uani 1 1 d . . . . .
H4A H 0.426882 0.337263 0.133733 0.030 Uiso 1 1 calc R U . . .
H4B H 0.411545 0.391579 0.261835 0.030 Uiso 1 1 calc R U . . .
C17 C 1.0054(3) 0.6230(3) 0.3667(3) 0.0262(7) Uani 1 1 d . . . . .
C16 C 0.9322(3) 0.5476(3) 0.2906(3) 0.0249(6) Uani 1 1 d . . . . .
C15 C 0.6158(3) 0.2958(3) 0.1745(3) 0.0279(7) Uani 1 1 d . . . . .
H15A H 0.690914 0.288090 0.208882 0.042 Uiso 1 1 calc R U . . .
H15B H 0.605309 0.320816 0.088702 0.042 Uiso 1 1 calc R U . . .
H15C H 0.581314 0.220086 0.178906 0.042 Uiso 1 1 calc R U . . .
C22 C 0.9759(3) 0.6933(4) 0.4732(3) 0.0321(7) Uani 1 1 d . . . . .
H22A H 0.915911 0.744101 0.441134 0.048 Uiso 1 1 calc R U . . .
H22B H 1.035609 0.741373 0.512761 0.048 Uiso 1 1 calc R U . . .
H22C H 0.957401 0.638789 0.533333 0.048 Uiso 1 1 calc R U . . .
C10 C 0.8212(3) 0.5300(3) 0.3151(3) 0.0265(7) Uani 1 1 d . . . . .
H10 H 0.811534 0.584335 0.382326 0.032 Uiso 1 1 calc R U . . .
C19 C 1.1378(3) 0.5715(4) 0.2461(3) 0.0331(8) Uani 1 1 d . . . . .
H19 H 1.206696 0.579950 0.231969 0.040 Uiso 1 1 calc R U . . .
C20 C 1.0649(3) 0.4966(4) 0.1705(3) 0.0322(8) Uani 1 1 d . . . . .
H20 H 1.084467 0.455004 0.105055 0.039 Uiso 1 1 calc R U . . .
C18 C 1.1072(3) 0.6333(3) 0.3426(3) 0.0304(7) Uani 1 1 d . . . . .
H18 H 1.156491 0.683201 0.392748 0.036 Uiso 1 1 calc R U . . .
C21 C 0.9630(3) 0.4844(3) 0.1933(3) 0.0307(7) Uani 1 1 d . . . . .
H21 H 0.914382 0.433512 0.143408 0.037 Uiso 1 1 calc R U . . .
B1 B 0.6128(3) 0.5264(3) 0.2421(3) 0.0204(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I12 C9 2.174(3) . ?
F11 C10 1.435(4) . ?
O8 C7 1.333(4) . ?
O8 B1 1.479(4) . ?
O2 C3 1.336(4) . ?
O2 B1 1.468(4) . ?
O14 C7 1.206(4) . ?
O13 C3 1.204(4) . ?
N5 C15 1.493(4) . ?
N5 C6 1.495(4) . ?
N5 C4 1.502(4) . ?
N5 B1 1.663(4) . ?
C7 C6 1.511(4) . ?
C9 C10 1.515(4) . ?
C9 B1 1.611(5) . ?
C9 H9 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 C4 1.499(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C17 C18 1.387(5) . ?
C17 C16 1.398(5) . ?
C17 C22 1.515(5) . ?
C16 C21 1.399(5) . ?
C16 C10 1.511(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C10 H10 0.9800 . ?
C19 C18 1.382(5) . ?
C19 C20 1.389(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(5) . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C21 H21 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 O8 B1 114.1(2) . . ?
C3 O2 B1 113.6(2) . . ?
C15 N5 C6 111.8(2) . . ?
C15 N5 C4 110.1(3) . . ?
C6 N5 C4 111.2(2) . . ?
C15 N5 B1 116.3(2) . . ?
C6 N5 B1 104.2(2) . . ?
C4 N5 B1 102.8(2) . . ?
O14 C7 O8 124.2(3) . . ?
O14 C7 C6 124.5(3) . . ?
O8 C7 C6 111.3(2) . . ?
C10 C9 B1 113.7(3) . . ?
C10 C9 I12 106.5(2) . . ?
B1 C9 I12 108.6(2) . . ?
C10 C9 H9 109.3 . . ?
B1 C9 H9 109.3 . . ?
I12 C9 H9 109.3 . . ?
N5 C6 C7 105.7(2) . . ?
N5 C6 H6A 110.6 . . ?
C7 C6 H6A 110.6 . . ?
N5 C6 H6B 110.6 . . ?
C7 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
O13 C3 O2 123.4(3) . . ?
O13 C3 C4 125.6(3) . . ?
O2 C3 C4 111.1(3) . . ?
C3 C4 N5 107.2(3) . . ?
C3 C4 H4A 110.3 . . ?
N5 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
N5 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
C18 C17 C16 118.4(3) . . ?
C18 C17 C22 119.9(3) . . ?
C16 C17 C22 121.8(3) . . ?
C17 C16 C21 119.8(3) . . ?
C17 C16 C10 120.6(3) . . ?
C21 C16 C10 119.5(3) . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F11 C10 C16 108.2(3) . . ?
F11 C10 C9 104.5(3) . . ?
C16 C10 C9 117.6(3) . . ?
F11 C10 H10 108.8 . . ?
C16 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C19 C18 C17 122.0(3) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C20 C21 C16 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
O2 B1 O8 110.5(3) . . ?
O2 B1 C9 113.3(2) . . ?
O8 B1 C9 112.4(3) . . ?
O2 B1 N5 101.8(2) . . ?
O8 B1 N5 100.2(2) . . ?
C9 B1 N5 117.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 O8 C7 O14 171.8(3) . . . . ?
B1 O8 C7 C6 -8.4(3) . . . . ?
C15 N5 C6 C7 143.2(3) . . . . ?
C4 N5 C6 C7 -93.3(3) . . . . ?
B1 N5 C6 C7 16.7(3) . . . . ?
O14 C7 C6 N5 173.0(3) . . . . ?
O8 C7 C6 N5 -6.7(3) . . . . ?
B1 O2 C3 O13 169.9(3) . . . . ?
B1 O2 C3 C4 -10.1(3) . . . . ?
O13 C3 C4 N5 176.5(3) . . . . ?
O2 C3 C4 N5 -3.5(3) . . . . ?
C15 N5 C4 C3 -111.2(3) . . . . ?
C6 N5 C4 C3 124.3(3) . . . . ?
B1 N5 C4 C3 13.3(3) . . . . ?
C18 C17 C16 C21 0.3(5) . . . . ?
C22 C17 C16 C21 -179.9(3) . . . . ?
C18 C17 C16 C10 178.1(3) . . . . ?
C22 C17 C16 C10 -2.2(5) . . . . ?
C17 C16 C10 F11 -112.2(3) . . . . ?
C21 C16 C10 F11 65.5(4) . . . . ?
C17 C16 C10 C9 129.9(3) . . . . ?
C21 C16 C10 C9 -52.4(5) . . . . ?
B1 C9 C10 F11 61.1(3) . . . . ?
I12 C9 C10 F11 -179.32(19) . . . . ?
B1 C9 C10 C16 -179.1(3) . . . . ?
I12 C9 C10 C16 -59.4(3) . . . . ?
C18 C19 C20 C21 -0.4(6) . . . . ?
C20 C19 C18 C17 0.0(6) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C22 C17 C18 C19 -179.7(3) . . . . ?
C19 C20 C21 C16 0.8(6) . . . . ?
C17 C16 C21 C20 -0.7(5) . . . . ?
C10 C16 C21 C20 -178.5(3) . . . . ?
C3 O2 B1 O8 -88.1(3) . . . . ?
C3 O2 B1 C9 144.7(3) . . . . ?
C3 O2 B1 N5 17.7(3) . . . . ?
C7 O8 B1 O2 124.8(3) . . . . ?
C7 O8 B1 C9 -107.5(3) . . . . ?
C7 O8 B1 N5 17.9(3) . . . . ?
C10 C9 B1 O2 158.6(3) . . . . ?
I12 C9 B1 O2 40.2(3) . . . . ?
C10 C9 B1 O8 32.3(4) . . . . ?
I12 C9 B1 O8 -86.1(3) . . . . ?
C10 C9 B1 N5 -83.1(3) . . . . ?
I12 C9 B1 N5 158.5(2) . . . . ?
C15 N5 B1 O2 102.3(3) . . . . ?
C6 N5 B1 O2 -134.2(2) . . . . ?
C4 N5 B1 O2 -18.1(3) . . . . ?
C15 N5 B1 O8 -144.1(3) . . . . ?
C6 N5 B1 O8 -20.5(3) . . . . ?
C4 N5 B1 O8 95.6(2) . . . . ?
C15 N5 B1 C9 -22.1(4) . . . . ?
C6 N5 B1 C9 101.4(3) . . . . ?
C4 N5 B1 C9 -142.5(3) . . . . ?

_refine_diff_density_max         1.171
_refine_diff_density_min         -1.021
_refine_diff_density_rms         0.106

