# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_en0737366
_database_code_depnum_ccdc_archive 'CCDC 1474833'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-06-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_en0737366           
;
PROBLEM: Hirshfeld Test Diff for    S2     --  C       ..       15.9 s.u.
RESPONSE: This error relates to the split redundancy of the Thiophene ring which we could not successfully model. 
;
# Added during the CSD deposition process: Monday 18 April 2016 03:52 PM
# end Validation Reply Form

_audit_creation_date             2016-04-18
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
2-(2-fluoro-4-methyl-5-(thiophen-3-yl)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
_chemical_formula_moiety         'C16 H15 B F N O4 S'
_chemical_formula_sum            'C16 H15 B F N O4 S'
_chemical_formula_weight         347.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H9BBrFNO4
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.1992(4)
_cell_length_b                   9.7061(3)
_cell_length_c                   13.4162(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.061(3)
_cell_angle_gamma                90
_cell_volume                     1572.87(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4235
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      71.0940
_cell_measurement_theta_min      3.6590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8086
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.276
_diffrn_reflns_theta_min         3.659
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -109.00  -66.00   1.0000   16.6800
omega____ theta____ kappa____ phi______ frames
    -      -36.7513 -178.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   10.00  103.00   1.0000   16.6800
omega____ theta____ kappa____ phi______ frames
    -       36.7513   77.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   93.00   1.0000   16.6800
omega____ theta____ kappa____ phi______ frames
    -       36.7513    0.0000    0.0000 124

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00   76.00   1.0000   16.6800
omega____ theta____ kappa____ phi______ frames
    -       36.7513  -99.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
  5 omega   37.00   68.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   68.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   44.00  130.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -93.0000  115.7107 86

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   64.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   69.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   41.00   77.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   68.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00   69.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 13 omega   49.00   77.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   76.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
 15 omega   38.00   68.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00   71.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   77.00  103.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000   15.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  110.00  164.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000   15.0000   90.0000 54

#__ type_ start__ end____ width___ exp.time_
 19 omega   69.00  166.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000   15.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 20 omega   40.00  138.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -92.0000  -25.0814 98

#__ type_ start__ end____ width___ exp.time_
 21 omega   49.00  117.00   1.0000   66.7300
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -93.0000 -125.4890 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0489997000
_diffrn_orient_matrix_UB_12      0.1353085000
_diffrn_orient_matrix_UB_13      0.0469613000
_diffrn_orient_matrix_UB_21      0.0881436000
_diffrn_orient_matrix_UB_22      -0.0824806000
_diffrn_orient_matrix_UB_23      0.0689227000
_diffrn_orient_matrix_UB_31      0.0780882000
_diffrn_orient_matrix_UB_32      0.0081541000
_diffrn_orient_matrix_UB_33      -0.0806400000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2554
_reflns_number_total             2977
_reflns_odcompleteness_completeness 99.47
_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, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         2977
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.062
_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)+(0.1234P)²+0.8550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1751
_refine_ls_wR_factor_ref         0.1846
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C021(H021), C(H)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O11 O 0.19537(15) 0.50767(18) -0.27491(14) 0.0289(4) Uani 1 1 d . . . . .
F F 0.32117(13) 0.33148(18) -0.53501(12) 0.0365(4) Uani 1 1 d . . . . .
O10 O 0.15530(16) 0.47013(18) -0.45684(13) 0.0288(4) Uani 1 1 d . . . . .
O0AA O 0.07249(17) 0.5368(2) -0.16787(15) 0.0384(5) Uani 1 1 d . . . . .
C22 C 0.3891(2) 0.3544(3) -0.44695(19) 0.0270(5) Uani 1 1 d . . . . .
C23 C 0.5011(2) 0.3412(3) -0.44920(19) 0.0287(6) Uani 1 1 d . . . . .
O O 0.05291(18) 0.3875(2) -0.59531(14) 0.0407(5) Uani 1 1 d . . . . .
C27 C 0.4188(2) 0.4014(3) -0.27387(19) 0.0264(5) Uani 1 1 d . . . . .
C24 C 0.5757(2) 0.3595(2) -0.36194(19) 0.0266(5) Uani 1 1 d . . . . .
C30 C 0.1056(2) 0.4743(3) -0.23523(19) 0.0280(5) Uani 1 1 d . . . . .
C32 C 0.0955(2) 0.3749(3) -0.50901(18) 0.0284(6) Uani 1 1 d . . . . .
C28 C 0.3422(2) 0.3887(2) -0.36159(18) 0.0255(5) Uani 1 1 d . . . . .
C33 C 0.0894(2) 0.2448(3) -0.44722(18) 0.0267(5) Uani 1 1 d . . . . .
C34 C 0.1937(2) 0.1693(3) -0.28407(19) 0.0267(5) Uani 1 1 d . . . . .
C29 C 0.6058(2) 0.4026(3) -0.17409(19) 0.0270(5) Uani 1 1 d . . . . .
C25 C 0.6982(2) 0.3555(3) -0.3685(2) 0.0339(6) Uani 1 1 d . . . . .
C26 C 0.5333(2) 0.3855(2) -0.27133(19) 0.0258(5) Uani 1 1 d . . . . .
C021 C 0.7025(2) 0.3235(3) -0.1407(2) 0.0350(6) Uani 1 1 d . . . . .
H021 H 0.7264 0.2497 -0.1789 0.042 Uiso 1 1 calc R . . . .
C C 0.7613(2) 0.3643(3) -0.04397(19) 0.0306(6) Uani 1 1 d . . . . .
H H 0.8292 0.3274 -0.0116 0.037 Uiso 1 1 calc R . . . .
C31 C 0.0506(2) 0.3478(3) -0.28578(18) 0.0252(5) Uani 1 1 d . . . . .
B B 0.2139(2) 0.4185(3) -0.3598(2) 0.0246(6) Uani 1 1 d . . . . .
S2 S 0.68328(7) 0.49400(8) 0.00126(6) 0.0427(3) Uani 1 1 d . . . . .
C35 C 0.5865(2) 0.4986(3) -0.1031(2) 0.0313(6) Uani 1 1 d . . . . .
H35 H 0.530(3) 0.565(4) -0.109(2) 0.032(8) Uiso 1 1 d . . . . .
H34A H 0.226(3) 0.205(3) -0.213(2) 0.030(7) Uiso 1 1 d . . . . .
H31A H -0.016(3) 0.382(3) -0.333(3) 0.036(8) Uiso 1 1 d . . . . .
H33A H 0.136(3) 0.179(3) -0.472(2) 0.028(7) Uiso 1 1 d . . . . .
H34B H 0.252(3) 0.138(3) -0.318(2) 0.021(7) Uiso 1 1 d . . . . .
H33B H 0.020(3) 0.214(4) -0.459(2) 0.033(8) Uiso 1 1 d . . . . .
H34C H 0.139(3) 0.093(4) -0.275(3) 0.036(8) Uiso 1 1 d . . . . .
H31B H 0.028(3) 0.285(3) -0.239(2) 0.027(7) Uiso 1 1 d . . . . .
H25A H 0.742(3) 0.421(4) -0.322(3) 0.047(10) Uiso 1 1 d . . . . .
H25B H 0.729(3) 0.263(4) -0.349(2) 0.035(8) Uiso 1 1 d . . . . .
H25C H 0.706(3) 0.367(3) -0.442(3) 0.034(8) Uiso 1 1 d . . . . .
H23 H 0.531(3) 0.314(4) -0.512(3) 0.051(10) Uiso 1 1 d . . . . .
H27 H 0.391(3) 0.424(3) -0.207(2) 0.027(7) Uiso 1 1 d . . . . .
N1 N 0.13566(16) 0.2849(2) -0.34284(14) 0.0211(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C30 1.324(3) . ?
O11 B 1.472(3) . ?
F C22 1.363(3) . ?
O10 C32 1.316(3) . ?
O10 B 1.482(3) . ?
O0AA C30 1.204(3) . ?
C22 C23 1.378(4) . ?
C22 C28 1.390(3) . ?
C23 C24 1.389(4) . ?
C23 H23 1.00(4) . ?
O C32 1.207(3) . ?
C27 C28 1.402(4) . ?
C27 C26 1.400(4) . ?
C27 H27 1.02(3) . ?
C24 C25 1.510(4) . ?
C24 C26 1.409(3) . ?
C30 C31 1.514(4) . ?
C32 C33 1.518(4) . ?
C28 B 1.596(4) . ?
C33 H33A 0.94(3) . ?
C33 H33B 0.89(4) . ?
C33 N1 1.486(3) . ?
C34 H34A 1.03(3) . ?
C34 H34B 0.95(3) . ?
C34 H34C 1.02(4) . ?
C34 N1 1.492(3) . ?
C29 C26 1.479(4) . ?
C29 C021 1.425(4) . ?
C29 C35 1.377(4) . ?
C25 H25A 0.99(4) . ?
C25 H25B 1.00(4) . ?
C25 H25C 1.02(3) . ?
C021 H021 0.9500 . ?
C021 C 1.447(4) . ?
C H 0.9500 . ?
C S2 1.738(3) . ?
C31 H31A 1.02(4) . ?
C31 H31B 0.95(3) . ?
C31 N1 1.503(3) . ?
B N1 1.644(3) . ?
S2 C35 1.700(3) . ?
C35 H35 0.94(4) . ?

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
C30 O11 B 113.1(2) . . ?
C32 O10 B 113.12(19) . . ?
F C22 C23 116.8(2) . . ?
F C22 C28 118.9(2) . . ?
C23 C22 C28 124.3(2) . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 H23 122(2) . . ?
C24 C23 H23 118(2) . . ?
C28 C27 H27 119.5(17) . . ?
C26 C27 C28 123.8(2) . . ?
C26 C27 H27 116.7(17) . . ?
C23 C24 C25 118.9(2) . . ?
C23 C24 C26 118.3(2) . . ?
C26 C24 C25 122.7(2) . . ?
O11 C30 C31 111.0(2) . . ?
O0AA C30 O11 124.2(3) . . ?
O0AA C30 C31 124.8(3) . . ?
O10 C32 C33 111.1(2) . . ?
O C32 O10 124.8(3) . . ?
O C32 C33 124.1(3) . . ?
C22 C28 C27 114.2(2) . . ?
C22 C28 B 125.0(2) . . ?
C27 C28 B 120.7(2) . . ?
C32 C33 H33A 107.0(19) . . ?
C32 C33 H33B 108(2) . . ?
H33A C33 H33B 108(3) . . ?
N1 C33 C32 104.8(2) . . ?
N1 C33 H33A 109.5(19) . . ?
N1 C33 H33B 119(2) . . ?
H34A C34 H34B 110(2) . . ?
H34A C34 H34C 108(3) . . ?
H34B C34 H34C 112(3) . . ?
N1 C34 H34A 108.8(18) . . ?
N1 C34 H34B 108.6(17) . . ?
N1 C34 H34C 109.7(19) . . ?
C021 C29 C26 125.7(2) . . ?
C35 C29 C26 123.1(2) . . ?
C35 C29 C021 111.2(2) . . ?
C24 C25 H25A 113(2) . . ?
C24 C25 H25B 110(2) . . ?
C24 C25 H25C 106.4(19) . . ?
H25A C25 H25B 105(3) . . ?
H25A C25 H25C 115(3) . . ?
H25B C25 H25C 106(3) . . ?
C27 C26 C24 119.0(2) . . ?
C27 C26 C29 118.7(2) . . ?
C24 C26 C29 122.3(2) . . ?
C29 C021 H021 122.6 . . ?
C29 C021 C 114.8(2) . . ?
C C021 H021 122.6 . . ?
C021 C H 126.7 . . ?
C021 C S2 106.5(2) . . ?
S2 C H 126.7 . . ?
C30 C31 H31A 106.3(19) . . ?
C30 C31 H31B 112.1(19) . . ?
H31A C31 H31B 110(3) . . ?
N1 C31 C30 105.24(19) . . ?
N1 C31 H31A 111.4(19) . . ?
N1 C31 H31B 111.6(19) . . ?
O11 B O10 111.9(2) . . ?
O11 B C28 112.1(2) . . ?
O11 B N1 101.64(18) . . ?
O10 B C28 113.6(2) . . ?
O10 B N1 99.82(19) . . ?
C28 B N1 116.66(19) . . ?
C35 S2 C 94.73(14) . . ?
C29 C35 S2 112.7(2) . . ?
C29 C35 H35 127(2) . . ?
S2 C35 H35 120(2) . . ?
C33 N1 C34 112.96(19) . . ?
C33 N1 C31 112.85(18) . . ?
C33 N1 B 103.13(17) . . ?
C34 N1 C31 110.28(18) . . ?
C34 N1 B 115.12(18) . . ?
C31 N1 B 101.89(17) . . ?

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
O11 C30 C31 N1 15.1(3) . . . . ?
O11 B N1 C33 142.58(19) . . . . ?
O11 B N1 C34 -93.9(2) . . . . ?
O11 B N1 C31 25.4(2) . . . . ?
F C22 C23 C24 -178.4(2) . . . . ?
F C22 C28 C27 176.1(2) . . . . ?
F C22 C28 B -6.4(4) . . . . ?
O10 C32 C33 N1 11.0(3) . . . . ?
O10 B N1 C33 27.6(2) . . . . ?
O10 B N1 C34 151.08(19) . . . . ?
O10 B N1 C31 -89.58(19) . . . . ?
O0AA C30 C31 N1 -164.9(2) . . . . ?
C22 C23 C24 C25 -175.2(2) . . . . ?
C22 C23 C24 C26 2.8(4) . . . . ?
C22 C28 B O11 -154.9(2) . . . . ?
C22 C28 B O10 -26.8(3) . . . . ?
C22 C28 B N1 88.5(3) . . . . ?
C23 C22 C28 C27 -3.7(4) . . . . ?
C23 C22 C28 B 173.8(2) . . . . ?
C23 C24 C26 C27 -4.4(3) . . . . ?
C23 C24 C26 C29 178.3(2) . . . . ?
O C32 C33 N1 -170.4(2) . . . . ?
C27 C28 B O11 22.4(3) . . . . ?
C27 C28 B O10 150.5(2) . . . . ?
C27 C28 B N1 -94.1(3) . . . . ?
C30 O11 B O10 87.7(2) . . . . ?
C30 O11 B C28 -143.3(2) . . . . ?
C30 O11 B N1 -18.0(3) . . . . ?
C30 C31 N1 C33 -134.1(2) . . . . ?
C30 C31 N1 C34 98.6(2) . . . . ?
C30 C31 N1 B -24.1(2) . . . . ?
C32 O10 B O11 -129.6(2) . . . . ?
C32 O10 B C28 102.2(2) . . . . ?
C32 O10 B N1 -22.7(2) . . . . ?
C32 C33 N1 C34 -148.5(2) . . . . ?
C32 C33 N1 C31 85.6(2) . . . . ?
C32 C33 N1 B -23.5(2) . . . . ?
C28 C22 C23 C24 1.4(4) . . . . ?
C28 C27 C26 C24 2.0(4) . . . . ?
C28 C27 C26 C29 179.5(2) . . . . ?
C28 B N1 C33 -95.2(2) . . . . ?
C28 B N1 C34 28.2(3) . . . . ?
C28 B N1 C31 147.6(2) . . . . ?
C29 C021 C S2 3.9(3) . . . . ?
C25 C24 C26 C27 173.5(2) . . . . ?
C25 C24 C26 C29 -3.9(4) . . . . ?
C26 C27 C28 C22 1.9(4) . . . . ?
C26 C27 C28 B -175.7(2) . . . . ?
C26 C29 C021 C 177.8(2) . . . . ?
C26 C29 C35 S2 179.75(18) . . . . ?
C021 C29 C26 C27 142.4(3) . . . . ?
C021 C29 C26 C24 -40.2(4) . . . . ?
C021 C29 C35 S2 0.3(3) . . . . ?
C021 C S2 C35 -3.1(2) . . . . ?
C S2 C35 C29 1.7(2) . . . . ?
B O11 C30 O0AA -177.0(2) . . . . ?
B O11 C30 C31 3.0(3) . . . . ?
B O10 C32 O -169.6(2) . . . . ?
B O10 C32 C33 8.9(3) . . . . ?
C35 C29 C26 C27 -37.0(3) . . . . ?
C35 C29 C26 C24 140.4(3) . . . . ?
C35 C29 C021 C -2.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 1417523859.75
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method MeCN
####################################################################### 
# 
# 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_10br01
_database_code_depnum_ccdc_archive 'CCDC 1474834'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-06-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_10br01              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.959 Note
RESPONSE: Only 96% of the data was used to fully solve this structure. 
;
# Added during the CSD deposition process: Monday 18 April 2016 04:03 PM
# end Validation Reply Form

_audit_creation_date             2016-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '(5-acetamido-2-bromophenyl)boronic acid'
_chemical_formula_moiety         'C8 H9 B Br N O3'
_chemical_formula_sum            'C8 H9 B Br N O3'
_chemical_formula_weight         257.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c12 N2 O5 Br B H14'
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'
Br Br -0.6763 1.2805 '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                   7.2445(3)
_cell_length_b                   10.6254(5)
_cell_length_c                   12.4110(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.957(5)
_cell_angle_gamma                90
_cell_volume                     955.21(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1796
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      71.1780
_cell_measurement_theta_min      7.1020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.793
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3908
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.233
_diffrn_reflns_theta_min         5.481
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -57.00   1.00   12.13    --  -36.75-178.00  60.00   52
  2  ω     35.00 109.00   1.00   12.13    --   36.75 178.00-180.00   74
  3  ω     20.00 104.00   1.00   12.13    --   36.75  57.00 150.00   84
  4  ω     38.00  84.00   1.00   48.49    --  107.00 -95.00 120.00   46
  5  ω     38.00  84.00   1.00   48.49    --  107.00 -95.00 150.00   46
  6  ω     39.00  77.00   1.00   48.49    --  107.00 -45.00   0.00   38
  7  ω     39.00  77.00   1.00   48.49    --  107.00 -45.00 -30.00   38
  8  ω     37.00  69.00   1.00   48.49    --  107.00 -30.00 -90.00   32
  9  ω     37.00  69.00   1.00   48.49    --  107.00 -30.00 -60.00   32
 10  ω     40.00 125.00   1.00   48.49    --  107.00 -61.00-180.00   85
 11  ω   -109.00 -57.00   1.00   12.13    --  -36.75-178.00-150.00   52
 12  ω     20.00 104.00   1.00   12.13    --   36.75  57.00-120.00   84
 13  ω     10.00 104.00   1.00   12.13    --   36.75  77.00 -30.00   94
 14  ω     86.00 125.00   1.00   48.49    --  107.00  30.00-120.00   39
 15  ω     38.00 176.00   1.00   48.49    --  107.00   0.00  30.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1616622000
_diffrn_orient_matrix_UB_12      0.0860719000
_diffrn_orient_matrix_UB_13      -0.0344879000
_diffrn_orient_matrix_UB_21      0.1119879000
_diffrn_orient_matrix_UB_22      0.0468941000
_diffrn_orient_matrix_UB_23      -0.0964012000
_diffrn_orient_matrix_UB_31      -0.0809636000
_diffrn_orient_matrix_UB_32      -0.1067715000
_diffrn_orient_matrix_UB_33      -0.0702943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1512
_reflns_number_total             1737
_reflns_odcompleteness_completeness 95.54
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.055
_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)+(0.0721P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1175
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C8(H8)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_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
Br1 Br 0.62224(5) 0.87314(3) 0.41176(3) 0.03075(19) Uani 1 1 d . . . . .
O1 O 0.7977(4) 0.3205(3) 0.7029(2) 0.0313(6) Uani 1 1 d . . . . .
O2 O 0.8604(4) 0.6648(3) 0.1795(2) 0.0321(6) Uani 1 1 d . . . . .
H2 H 0.9532 0.6513 0.2193 0.048 Uiso 1 1 calc GR . . . .
O3 O 0.5468(4) 0.6791(3) 0.1826(2) 0.0334(6) Uani 1 1 d . . . . .
H3 H 0.4583 0.6828 0.2254 0.050 Uiso 1 1 calc GR . . . .
N1 N 0.8147(4) 0.3301(3) 0.5198(2) 0.0276(6) Uani 1 1 d . . . . .
H1 H 0.8406 0.2847 0.4627 0.033 Uiso 1 1 calc R . . . .
C1 C 0.8775(6) 0.1328(4) 0.6083(4) 0.0350(9) Uani 1 1 d . . . . .
H1A H 0.9872 0.1171 0.6535 0.052 Uiso 1 1 calc GR . . . .
H1B H 0.9042 0.1113 0.5333 0.052 Uiso 1 1 calc GR . . . .
H1C H 0.7750 0.0808 0.6334 0.052 Uiso 1 1 calc GR . . . .
C2 C 0.8254(5) 0.2695(4) 0.6153(3) 0.0269(7) Uani 1 1 d . . . . .
C3 C 0.7673(5) 0.4569(3) 0.4998(3) 0.0239(7) Uani 1 1 d . . . . .
C4 C 0.7349(5) 0.5447(4) 0.5801(3) 0.0277(7) Uani 1 1 d . . . . .
H4 H 0.7429 0.5207 0.6537 0.033 Uiso 1 1 calc R . . . .
C5 C 0.6907(5) 0.6681(4) 0.5521(3) 0.0274(7) Uani 1 1 d . . . . .
H5 H 0.6690 0.7290 0.6065 0.033 Uiso 1 1 calc R . . . .
C6 C 0.6788(5) 0.7010(3) 0.4453(3) 0.0246(7) Uani 1 1 d . . . . .
C7 C 0.7132(5) 0.6176(3) 0.3620(3) 0.0219(7) Uani 1 1 d . . . . .
C8 C 0.7592(5) 0.4946(3) 0.3920(3) 0.0233(7) Uani 1 1 d . . . . .
H8 H 0.7857 0.4348 0.3374 0.028 Uiso 1 1 calc R . . . .
B1 B 0.7050(6) 0.6553(4) 0.2384(3) 0.0254(8) 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
Br1 C6 1.918(4) . ?
O1 C2 1.235(5) . ?
O2 H2 0.8400 . ?
O2 B1 1.356(5) . ?
O3 H3 0.8400 . ?
O3 B1 1.354(5) . ?
N1 H1 0.8800 . ?
N1 C2 1.349(5) . ?
N1 C3 1.412(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.504(5) . ?
C3 C4 1.387(5) . ?
C3 C8 1.397(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(5) . ?
C6 C7 1.387(5) . ?
C7 C8 1.398(5) . ?
C7 B1 1.585(5) . ?
C8 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O2 H2 109.5 . . ?
B1 O3 H3 109.5 . . ?
C2 N1 H1 115.8 . . ?
C2 N1 C3 128.3(3) . . ?
C3 N1 H1 115.8 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 N1 123.8(4) . . ?
O1 C2 C1 121.3(3) . . ?
N1 C2 C1 114.9(3) . . ?
C4 C3 N1 124.0(3) . . ?
C4 C3 C8 119.4(3) . . ?
C8 C3 N1 116.6(3) . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 Br1 117.5(3) . . ?
C5 C6 C7 123.2(3) . . ?
C7 C6 Br1 119.2(3) . . ?
C6 C7 C8 116.4(3) . . ?
C6 C7 B1 123.7(3) . . ?
C8 C7 B1 119.9(3) . . ?
C3 C8 C7 121.9(3) . . ?
C3 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
O2 B1 C7 121.5(3) . . ?
O3 B1 O2 114.4(3) . . ?
O3 B1 C7 124.1(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
Br1 C6 C7 C8 178.1(2) . . . . ?
Br1 C6 C7 B1 -1.2(5) . . . . ?
N1 C3 C4 C5 179.4(3) . . . . ?
N1 C3 C8 C7 179.8(3) . . . . ?
C2 N1 C3 C4 4.7(6) . . . . ?
C2 N1 C3 C8 -177.4(3) . . . . ?
C3 N1 C2 O1 -1.8(6) . . . . ?
C3 N1 C2 C1 179.1(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C3 C8 C7 -2.2(5) . . . . ?
C4 C5 C6 Br1 -178.8(3) . . . . ?
C4 C5 C6 C7 -1.6(6) . . . . ?
C5 C6 C7 C8 0.9(5) . . . . ?
C5 C6 C7 B1 -178.3(3) . . . . ?
C6 C7 C8 C3 1.0(5) . . . . ?
C6 C7 B1 O2 108.5(4) . . . . ?
C6 C7 B1 O3 -72.3(5) . . . . ?
C8 C3 C4 C5 1.5(5) . . . . ?
C8 C7 B1 O2 -70.7(5) . . . . ?
C8 C7 B1 O3 108.5(4) . . . . ?
B1 C7 C8 C3 -179.7(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 1425642948.52
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.783

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'MeCN and water'
####################################################################### 
# 
# 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_import
_database_code_depnum_ccdc_archive 'CCDC 1474835'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-06-14 downloaded from the CCDC.
;

_audit_creation_date             2012-11-28T11:38:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
5-bromo-2-fluoro-4-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)benzaldehyde
_chemical_formula_moiety         'C12 H10 B1 Br1 F1 N1 O5'
_chemical_formula_sum            'C12 H10 B Br F N O5'
_chemical_formula_weight         357.93
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2328(4)
_cell_length_b                   8.8504(2)
_cell_length_c                   13.6957(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.998(2)
_cell_angle_gamma                90
_cell_volume                     1340.88(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    14242
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.3764
_exptl_absorpt_correction_T_max  0.5042

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.441902E-1
_diffrn_orient_matrix_ub_12      -0.74785E-1
_diffrn_orient_matrix_ub_13      0.477864E-1
_diffrn_orient_matrix_ub_21      -0.77342E-1
_diffrn_orient_matrix_ub_22      -0.267242E-1
_diffrn_orient_matrix_ub_23      0.226101E-1
_diffrn_orient_matrix_ub_31      -0.154018E-1
_diffrn_orient_matrix_ub_32      -0.803716E-1
_diffrn_orient_matrix_ub_33      -0.519828E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.026
_diffrn_reflns_number            18233
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3062
_reflns_number_gt                2660
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0655P)²+0.9804P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3062
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.945
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.095

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5349(2) 1.0995(3) 0.13608(19) 0.0266(5) Uani 1 1 d . . .
C2 C 0.5964(2) 1.1788(3) 0.07083(18) 0.0233(5) Uani 1 1 d . . .
C3 C 0.5230(2) 1.2728(3) 0.00232(18) 0.0250(5) Uani 1 1 d . . .
H3 H 0.5586 1.3297 -0.044 0.03 Uiso 1 1 calc R . .
C4 C 0.4007(2) 1.2834(3) 0.0014(2) 0.0280(6) Uani 1 1 d . . .
C5 C 0.3417(2) 1.2067(3) 0.0668(2) 0.0260(5) Uani 1 1 d . . .
C6 C 0.4118(3) 1.1134(3) 0.1351(2) 0.0297(6) Uani 1 1 d . . .
H6 H 0.3751 1.0586 0.1817 0.036 Uiso 1 1 calc R . .
C7 C 0.2095(3) 1.2199(3) 0.0648(2) 0.0331(6) Uani 1 1 d . . .
H7 H 0.1615 1.269 0.01 0.04 Uiso 1 1 calc R . .
C8 C 0.8844(3) 1.0020(3) 0.1479(2) 0.0309(6) Uani 1 1 d . . .
C9 C 0.9063(2) 1.1411(3) 0.21242(19) 0.0265(5) Uani 1 1 d . . .
H9A H 0.8845 1.1215 0.2783 0.032 Uiso 1 1 calc R . .
H9B H 0.9925 1.1709 0.2218 0.032 Uiso 1 1 calc R . .
C10 C 0.8976(3) 1.3720(3) 0.10673(19) 0.0272(5) Uani 1 1 d . . .
H10A H 0.9843 1.3442 0.1183 0.033 Uiso 1 1 calc R . .
H10B H 0.8899 1.476 0.1314 0.033 Uiso 1 1 calc R . .
C11 C 0.8456(2) 1.3628(3) -0.00236(19) 0.0259(5) Uani 1 1 d . . .
C12 C 0.7637(2) 1.3482(3) 0.2296(2) 0.0294(6) Uani 1 1 d . . .
H12A H 0.7179 1.277 0.2635 0.044 Uiso 1 1 calc R . .
H12B H 0.7082 1.4219 0.1926 0.044 Uiso 1 1 calc R . .
H12C H 0.8231 1.4011 0.2787 0.044 Uiso 1 1 calc R . .
B1 B 0.7390(3) 1.1742(3) 0.0677(2) 0.0240(6) Uani 1 1 d . . .
Br1 Br 0.61859(3) 0.96604(4) 0.23392(2) 0.04436(15) Uani 1 1 d . . .
F3 F 0.33403(16) 1.3760(2) -0.06783(15) 0.0443(5) Uani 1 1 d . . .
N1 N 0.82779(19) 1.2638(2) 0.15936(15) 0.0215(4) Uani 1 1 d . . .
O1 O 0.1607(2) 1.1708(3) 0.13010(19) 0.0477(6) Uani 1 1 d . . .
O2 O 0.79257(19) 1.0236(2) 0.07310(15) 0.0316(4) Uani 1 1 d . . .
O3 O 0.76343(17) 1.2548(2) -0.02052(13) 0.0283(4) Uani 1 1 d . . .
O4 O 0.9397(2) 0.8865(2) 0.16302(18) 0.0437(6) Uani 1 1 d . . .
O5 O 0.8738(2) 1.4446(3) -0.06499(15) 0.0380(5) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(4) . ?
C1 C2 1.408(4) . ?
C1 Br1 1.907(3) . ?
C2 C3 1.408(4) . ?
C2 B1 1.610(4) . ?
C3 C4 1.376(4) . ?
C3 H3 0.95 . ?
C4 F3 1.373(3) . ?
C4 C5 1.381(4) . ?
C5 C6 1.386(4) . ?
C5 C7 1.485(4) . ?
C6 H6 0.95 . ?
C7 O1 1.208(4) . ?
C7 H7 0.95 . ?
C8 O4 1.196(4) . ?
C8 O2 1.335(3) . ?
C8 C9 1.511(4) . ?
C9 N1 1.504(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 N1 1.499(3) . ?
C10 C11 1.509(4) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 O5 1.206(3) . ?
C11 O3 1.322(3) . ?
C12 N1 1.498(3) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
B1 O2 1.459(4) . ?
B1 O3 1.470(3) . ?
B1 N1 1.662(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 123.3(2) . . ?
C6 C1 Br1 115.5(2) . . ?
C2 C1 Br1 121.2(2) . . ?
C3 C2 C1 115.0(2) . . ?
C3 C2 B1 117.9(2) . . ?
C1 C2 B1 127.2(2) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
F3 C4 C3 118.1(2) . . ?
F3 C4 C5 118.4(2) . . ?
C3 C4 C5 123.5(2) . . ?
C4 C5 C6 116.8(3) . . ?
C4 C5 C7 122.7(3) . . ?
C6 C5 C7 120.5(3) . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C5 122.7(3) . . ?
O1 C7 H7 118.7 . . ?
C5 C7 H7 118.7 . . ?
O4 C8 O2 124.4(3) . . ?
O4 C8 C9 124.6(3) . . ?
O2 C8 C9 111.0(2) . . ?
N1 C9 C8 106.4(2) . . ?
N1 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
N1 C9 H9B 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
N1 C10 C11 107.3(2) . . ?
N1 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
N1 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
O5 C11 O3 124.1(2) . . ?
O5 C11 C10 124.6(2) . . ?
O3 C11 C10 111.3(2) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 B1 O3 110.5(2) . . ?
O2 B1 C2 115.1(2) . . ?
O3 B1 C2 109.7(2) . . ?
O2 B1 N1 102.12(19) . . ?
O3 B1 N1 102.5(2) . . ?
C2 B1 N1 115.9(2) . . ?
C12 N1 C10 109.9(2) . . ?
C12 N1 C9 110.9(2) . . ?
C10 N1 C9 112.4(2) . . ?
C12 N1 B1 115.5(2) . . ?
C10 N1 B1 103.70(18) . . ?
C9 N1 B1 104.19(19) . . ?
C8 O2 B1 115.2(2) . . ?
C11 O3 B1 114.8(2) . . ?

# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
