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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_20161108b
_audit_block_doi                 10.5517/ccdc.csd.cc1n01nc
_database_code_depnum_ccdc_archive 'CCDC 1519392'
_audit_update_record             
;
2016-11-26 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_audit_creation_date             2016-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 B3 O3'
_chemical_formula_sum            'C18 H15 B3 O3'
_chemical_formula_weight         311.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1h1B1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.6824(5)
_cell_length_b                   13.2062(7)
_cell_length_c                   11.5423(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.843(6)
_cell_angle_gamma                90
_cell_volume                     1604.34(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2454
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.6920
_cell_measurement_theta_min      3.6490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale colourless'
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8240
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.897
_diffrn_reflns_theta_min         3.568
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  35.00   1.00    5.00    --   12.76 -99.00 150.00   43
  2  ω    -51.00  26.00   1.00    5.00    --   12.76 -37.00 -90.00   77
  3  ω    -62.00  17.00   1.00    5.00    --   12.76 -37.00-150.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0581004000
_diffrn_orient_matrix_UB_12      -0.0185586000
_diffrn_orient_matrix_UB_13      0.0319270000
_diffrn_orient_matrix_UB_21      -0.0101282000
_diffrn_orient_matrix_UB_22      0.0280516000
_diffrn_orient_matrix_UB_23      0.0499938000
_diffrn_orient_matrix_UB_31      -0.0326080000
_diffrn_orient_matrix_UB_32      -0.0418564000
_diffrn_orient_matrix_UB_33      0.0193213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2867
_reflns_number_total             3860
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_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         0.442
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.028
_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)+(0.0416P)²+0.6235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1243
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.85271(10) 0.46576(8) 0.72387(9) 0.0191(3) Uani 1 1 d . . . . .
O2 O 0.74456(10) 0.50360(8) 0.53064(9) 0.0189(3) Uani 1 1 d . . . . .
O3 O 0.67770(10) 0.57956(9) 0.69709(9) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.75858(14) 0.51565(12) 0.90427(13) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.66141(14) 0.56372(13) 0.95070(14) 0.0197(4) Uani 1 1 d . . . . .
H2 H 0.6000 0.6006 0.9013 0.024 Uiso 1 1 calc R . . . .
C3 C 0.65559(15) 0.55697(13) 1.06967(14) 0.0224(4) Uani 1 1 d . . . . .
H3 H 0.5899 0.5884 1.0994 0.027 Uiso 1 1 calc R . . . .
C4 C 0.74775(15) 0.50338(13) 1.14406(14) 0.0225(4) Uani 1 1 d . . . . .
H4 H 0.7445 0.4998 1.2240 0.027 Uiso 1 1 calc R . . . .
C5 C 0.84467(15) 0.45508(13) 1.10009(14) 0.0214(4) Uani 1 1 d . . . . .
H5 H 0.9066 0.4193 1.1503 0.026 Uiso 1 1 calc R . . . .
C6 C 0.84902(14) 0.46034(12) 0.98074(14) 0.0189(3) Uani 1 1 d . . . . .
H6 H 0.9131 0.4265 0.9512 0.023 Uiso 1 1 calc R . . . .
C7 C 0.93464(14) 0.38465(12) 0.55176(13) 0.0177(3) Uani 1 1 d . . . . .
C8 C 1.04360(15) 0.34586(12) 0.62156(14) 0.0197(4) Uani 1 1 d . . . . .
H8 H 1.0616 0.3631 0.7008 0.024 Uiso 1 1 calc R . . . .
C9 C 1.12568(15) 0.28217(13) 0.57523(15) 0.0235(4) Uani 1 1 d . . . . .
H9 H 1.1978 0.2570 0.6232 0.028 Uiso 1 1 calc R . . . .
C10 C 1.09999(16) 0.25615(13) 0.45716(15) 0.0254(4) Uani 1 1 d . . . . .
H10 H 1.1546 0.2133 0.4258 0.030 Uiso 1 1 calc R . . . .
C11 C 0.99295(17) 0.29412(14) 0.38637(15) 0.0275(4) Uani 1 1 d . . . . .
H11 H 0.9756 0.2766 0.3072 0.033 Uiso 1 1 calc R . . . .
C12 C 0.91151(16) 0.35796(13) 0.43257(14) 0.0241(4) Uani 1 1 d . . . . .
H12 H 0.8403 0.3836 0.3837 0.029 Uiso 1 1 calc R . . . .
C13 C 0.55867(14) 0.62712(12) 0.49560(13) 0.0176(3) Uani 1 1 d . . . . .
C14 C 0.53380(15) 0.61140(13) 0.37370(14) 0.0193(3) Uani 1 1 d . . . . .
H14 H 0.5836 0.5660 0.3399 0.023 Uiso 1 1 calc R . . . .
C15 C 0.43609(15) 0.66252(13) 0.30293(14) 0.0211(4) Uani 1 1 d . . . . .
H15 H 0.4200 0.6505 0.2224 0.025 Uiso 1 1 calc R . . . .
C17 C 0.36252(15) 0.73131(13) 0.35167(15) 0.0233(4) Uani 1 1 d . . . . .
H17 H 0.2977 0.7661 0.3038 0.028 Uiso 1 1 calc R . . . .
C18 C 0.38553(16) 0.74836(13) 0.47216(15) 0.0243(4) Uani 1 1 d . . . . .
H18 H 0.3364 0.7948 0.5052 0.029 Uiso 1 1 calc R . . . .
C19 C 0.48193(15) 0.69590(13) 0.54292(14) 0.0218(4) Uani 1 1 d . . . . .
H19 H 0.4958 0.7067 0.6237 0.026 Uiso 1 1 calc R . . . .
B1 B 0.76377(16) 0.52121(14) 0.77054(16) 0.0179(4) Uani 1 1 d . . . . .
B2 B 0.84155(17) 0.45418(14) 0.60337(16) 0.0177(4) Uani 1 1 d . . . . .
B3 B 0.66444(17) 0.56812(14) 0.57651(16) 0.0183(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.380(2) . ?
O1 B2 1.384(2) . ?
O2 B2 1.381(2) . ?
O2 B3 1.376(2) . ?
O3 B1 1.375(2) . ?
O3 B3 1.383(2) . ?
C1 C2 1.399(2) . ?
C1 C6 1.398(2) . ?
C1 B1 1.556(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.395(2) . ?
C7 C12 1.401(2) . ?
C7 B2 1.546(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.402(2) . ?
C13 C19 1.396(2) . ?
C13 B3 1.548(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9300 . ?
C15 C17 1.382(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(2) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 B2 120.28(13) . . ?
B3 O2 B2 120.67(13) . . ?
B1 O3 B3 120.13(13) . . ?
C2 C1 B1 120.87(14) . . ?
C6 C1 C2 118.24(14) . . ?
C6 C1 B1 120.87(14) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.75(15) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.92(15) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.34(15) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.66(15) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.07(15) . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C12 117.69(14) . . ?
C8 C7 B2 121.59(14) . . ?
C12 C7 B2 120.72(15) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.35(15) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.83(16) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.75(15) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.35(16) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.03(16) . . ?
C11 C12 H12 119.5 . . ?
C14 C13 B3 121.64(14) . . ?
C19 C13 C14 117.77(15) . . ?
C19 C13 B3 120.56(14) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 120.92(15) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.9 . . ?
C17 C15 C14 120.24(15) . . ?
C17 C15 H15 119.9 . . ?
C15 C17 H17 120.0 . . ?
C15 C17 C18 119.90(15) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.71(15) . . ?
C19 C18 H18 120.1 . . ?
C13 C19 H19 119.3 . . ?
C18 C19 C13 121.45(15) . . ?
C18 C19 H19 119.3 . . ?
O1 B1 C1 120.40(14) . . ?
O3 B1 O1 119.27(14) . . ?
O3 B1 C1 120.31(14) . . ?
O1 B2 C7 120.15(15) . . ?
O2 B2 O1 119.05(14) . . ?
O2 B2 C7 120.78(14) . . ?
O2 B3 O3 119.43(15) . . ?
O2 B3 C13 121.16(14) . . ?
O3 B3 C13 119.40(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
C2 C1 B1 O1 -173.82(15) . . . . ?
C2 C1 B1 O3 4.6(2) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C6 C1 B1 O1 4.5(2) . . . . ?
C6 C1 B1 O3 -177.06(15) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C7 C12 C11 1.0(2) . . . . ?
C8 C7 B2 O1 -11.0(2) . . . . ?
C8 C7 B2 O2 170.57(14) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C7 -0.7(3) . . . . ?
C12 C7 C8 C9 -0.7(2) . . . . ?
C12 C7 B2 O1 168.63(15) . . . . ?
C12 C7 B2 O2 -9.8(2) . . . . ?
C13 C14 C15 C17 1.0(2) . . . . ?
C14 C13 C19 C18 -1.0(2) . . . . ?
C14 C13 B3 O2 5.1(2) . . . . ?
C14 C13 B3 O3 -174.18(15) . . . . ?
C14 C15 C17 C18 -0.8(2) . . . . ?
C15 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 C13 1.2(3) . . . . ?
C19 C13 C14 C15 -0.1(2) . . . . ?
C19 C13 B3 O2 -176.98(15) . . . . ?
C19 C13 B3 O3 3.8(2) . . . . ?
B1 O1 B2 O2 3.7(2) . . . . ?
B1 O1 B2 C7 -174.80(14) . . . . ?
B1 O3 B3 O2 -4.9(2) . . . . ?
B1 O3 B3 C13 174.36(14) . . . . ?
B1 C1 C2 C3 178.72(15) . . . . ?
B1 C1 C6 C5 -179.93(15) . . . . ?
B2 O1 B1 O3 -11.6(2) . . . . ?
B2 O1 B1 C1 166.81(14) . . . . ?
B2 O2 B3 O3 -3.1(2) . . . . ?
B2 O2 B3 C13 177.61(14) . . . . ?
B2 C7 C8 C9 178.92(15) . . . . ?
B2 C7 C12 C11 -178.64(16) . . . . ?
B3 O2 B2 O1 3.7(2) . . . . ?
B3 O2 B2 C7 -177.80(15) . . . . ?
B3 O3 B1 O1 12.2(2) . . . . ?
B3 O3 B1 C1 -166.21(15) . . . . ?
B3 C13 C14 C15 177.93(15) . . . . ?
B3 C13 C19 C18 -179.04(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-08
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.146
_oxdiff_exptl_absorpt_empirical_full_min 0.837
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1547293'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 B O3'
_chemical_formula_weight         180.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   16.193(4)
_cell_length_b                   24.868(6)
_cell_length_c                   9.919(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.666(4)
_cell_angle_gamma                90.00
_cell_volume                     3981.2(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    57
_cell_measurement_theta_min      7.5
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26161
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         26.50
_reflns_number_total             8259
_reflns_number_gt                4433
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0672P)²+3.2830P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8259
_refine_ls_number_parameters     482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1955
_refine_ls_wR_factor_gt          0.1558
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 1.04787(19) 0.24741(13) 0.7184(3) 0.0424(7) Uani 1 1 d . . .
B2 B 0.4582(2) 0.25333(14) 0.7312(3) 0.0466(8) Uani 1 1 d . . .
B3 B 0.26574(19) 0.33883(13) 0.7327(3) 0.0420(7) Uani 1 1 d . . .
B4 B 0.24151(19) 0.33972(13) 0.2264(3) 0.0432(7) Uani 1 1 d . . .
C1 C 0.96422(16) 0.21702(11) 0.7042(2) 0.0434(6) Uani 1 1 d . . .
C2 C 0.90752(18) 0.22144(13) 0.8014(3) 0.0572(8) Uani 1 1 d . . .
H2 H 0.9220 0.2418 0.8784 0.069 Uiso 1 1 calc R . .
C3 C 0.83079(18) 0.19709(13) 0.7889(3) 0.0581(8) Uani 1 1 d . . .
H3 H 0.7938 0.2020 0.8548 0.070 Uiso 1 1 calc R . .
C4 C 0.80944(17) 0.16534(13) 0.6775(3) 0.0530(8) Uani 1 1 d . . .
C5 C 0.86371(19) 0.15983(14) 0.5799(3) 0.0621(9) Uani 1 1 d . . .
H5 H 0.8493 0.1388 0.5041 0.075 Uiso 1 1 calc R . .
C6 C 0.93939(18) 0.18512(12) 0.5926(3) 0.0526(7) Uani 1 1 d . . .
H6 H 0.9752 0.1808 0.5246 0.063 Uiso 1 1 calc R . .
C7 C 0.67685(19) 0.14265(15) 0.7524(3) 0.0689(10) Uani 1 1 d . . .
H7A H 0.6611 0.1799 0.7630 0.083 Uiso 1 1 calc R . .
H7B H 0.7002 0.1294 0.8393 0.083 Uiso 1 1 calc R . .
C8 C 0.6019(2) 0.1096(2) 0.7040(4) 0.0939(14) Uani 1 1 d . . .
H8A H 0.5766 0.1250 0.6208 0.113 Uiso 1 1 calc R . .
H8B H 0.6194 0.0733 0.6845 0.113 Uiso 1 1 calc R . .
C9 C 0.5403(3) 0.1075(2) 0.8044(5) 0.1231(18) Uani 1 1 d . . .
H9A H 0.5593 0.0837 0.8766 0.185 Uiso 1 1 calc R . .
H9B H 0.4886 0.0946 0.7623 0.185 Uiso 1 1 calc R . .
H9C H 0.5326 0.1429 0.8402 0.185 Uiso 1 1 calc R . .
C10 C 0.54196(16) 0.28279(11) 0.7288(2) 0.0435(6) Uani 1 1 d . . .
C11 C 0.59197(19) 0.27764(14) 0.6224(3) 0.0593(8) Uani 1 1 d . . .
H11 H 0.5720 0.2583 0.5465 0.071 Uiso 1 1 calc R . .
C12 C 0.67008(19) 0.29993(14) 0.6243(3) 0.0618(9) Uani 1 1 d . . .
H12 H 0.7021 0.2949 0.5517 0.074 Uiso 1 1 calc R . .
C13 C 0.70016(18) 0.32961(13) 0.7341(3) 0.0537(8) Uani 1 1 d . . .
C14 C 0.65158(19) 0.33711(13) 0.8398(3) 0.0596(8) Uani 1 1 d . . .
H14 H 0.6713 0.3577 0.9138 0.072 Uiso 1 1 calc R . .
C15 C 0.57418(18) 0.31443(12) 0.8371(3) 0.0522(7) Uani 1 1 d . . .
H15 H 0.5422 0.3203 0.9095 0.063 Uiso 1 1 calc R . .
C16 C 0.8301(2) 0.34613(17) 0.6412(4) 0.0769(11) Uani 1 1 d . . .
H16A H 0.8077 0.3658 0.5620 0.092 Uiso 1 1 calc R . .
H16B H 0.8332 0.3084 0.6173 0.092 Uiso 1 1 calc R . .
C17 C 0.9160(3) 0.3670(2) 0.6864(5) 0.0996(14) Uani 1 1 d . . .
H17A H 0.9371 0.3474 0.7664 0.120 Uiso 1 1 calc R . .
H17B H 0.9526 0.3599 0.6158 0.120 Uiso 1 1 calc R . .
C18 C 0.9181(3) 0.4226(2) 0.7157(6) 0.1321(19) Uani 1 1 d . . .
H18A H 0.8907 0.4421 0.6414 0.198 Uiso 1 1 calc R . .
H18B H 0.9746 0.4344 0.7296 0.198 Uiso 1 1 calc R . .
H18C H 0.8904 0.4293 0.7961 0.198 Uiso 1 1 calc R . .
C19 C 0.34236(16) 0.37648(11) 0.7464(2) 0.0426(6) Uani 1 1 d . . .
C20 C 0.39210(17) 0.38531(12) 0.6408(3) 0.0490(7) Uani 1 1 d . . .
H20 H 0.3788 0.3681 0.5586 0.059 Uiso 1 1 calc R . .
C21 C 0.46069(18) 0.41867(13) 0.6530(3) 0.0546(8) Uani 1 1 d . . .
H21 H 0.4926 0.4236 0.5802 0.065 Uiso 1 1 calc R . .
C22 C 0.48148(18) 0.44464(12) 0.7741(3) 0.0513(7) Uani 1 1 d . . .
C23 C 0.43262(19) 0.43737(13) 0.8808(3) 0.0579(8) Uani 1 1 d . . .
H23 H 0.4456 0.4551 0.9623 0.070 Uiso 1 1 calc R . .
C24 C 0.36496(18) 0.40397(12) 0.8665(3) 0.0523(7) Uani 1 1 d . . .
H24 H 0.3330 0.3995 0.9395 0.063 Uiso 1 1 calc R . .
C25 C 0.6070(2) 0.48163(15) 0.7004(4) 0.0720(10) Uani 1 1 d . . .
H25A H 0.5826 0.4997 0.6201 0.086 Uiso 1 1 calc R . .
H25B H 0.6251 0.4461 0.6749 0.086 Uiso 1 1 calc R . .
C26 C 0.6794(2) 0.51369(16) 0.7634(4) 0.0867(12) Uani 1 1 d . . .
H26A H 0.6598 0.5489 0.7886 0.104 Uiso 1 1 calc R . .
H26B H 0.7191 0.5189 0.6965 0.104 Uiso 1 1 calc R . .
C27 C 0.7231(3) 0.48724(19) 0.8875(5) 0.1082(15) Uani 1 1 d . . .
H27A H 0.6852 0.4840 0.9566 0.162 Uiso 1 1 calc R . .
H27B H 0.7696 0.5088 0.9203 0.162 Uiso 1 1 calc R . .
H27C H 0.7421 0.4522 0.8639 0.162 Uiso 1 1 calc R . .
C28 C 0.16202(16) 0.37484(11) 0.2259(3) 0.0443(6) Uani 1 1 d . . .
C29 C 0.12824(19) 0.40000(13) 0.1072(3) 0.0588(8) Uani 1 1 d . . .
H29 H 0.1541 0.3953 0.0278 0.071 Uiso 1 1 calc R . .
C30 C 0.0587(2) 0.43122(14) 0.1045(3) 0.0674(9) Uani 1 1 d . . .
H30 H 0.0388 0.4479 0.0244 0.081 Uiso 1 1 calc R . .
C31 C 0.01816(19) 0.43805(13) 0.2189(3) 0.0584(8) Uani 1 1 d . . .
C32 C 0.0493(2) 0.41472(14) 0.3379(3) 0.0646(9) Uani 1 1 d . . .
H32 H 0.0228 0.4196 0.4166 0.078 Uiso 1 1 calc R . .
C33 C 0.12056(19) 0.38379(13) 0.3398(3) 0.0581(8) Uani 1 1 d . . .
H33 H 0.1412 0.3685 0.4211 0.070 Uiso 1 1 calc R . .
C37 C -0.1020(2) 0.47038(16) 0.3146(4) 0.0797(11) Uani 1 1 d . . .
H37A H -0.0721 0.4880 0.3910 0.096 Uiso 1 1 calc R . .
H37B H -0.1154 0.4341 0.3414 0.096 Uiso 1 1 calc R . .
C38 C -0.1799(2) 0.5008(2) 0.2733(5) 0.1036(15) Uani 1 1 d . . .
H38A H -0.2089 0.4836 0.1954 0.124 Uiso 1 1 calc R . .
H38B H -0.1663 0.5372 0.2481 0.124 Uiso 1 1 calc R . .
C39 C -0.2352(3) 0.5021(2) 0.3895(5) 0.1170(17) Uani 1 1 d . . .
H39A H -0.2396 0.4665 0.4259 0.176 Uiso 1 1 calc R . .
H39B H -0.2893 0.5147 0.3574 0.176 Uiso 1 1 calc R . .
H39C H -0.2118 0.5258 0.4588 0.176 Uiso 1 1 calc R . .
O1 O 0.73580(13) 0.13856(11) 0.6560(2) 0.0760(7) Uani 1 1 d . . .
O2 O 1.09502(11) 0.25766(9) 0.61264(17) 0.0535(5) Uani 1 1 d . . .
H2A H 1.0699 0.2480 0.5417 0.080 Uiso 1 1 calc R . .
O3 O 1.07769(12) 0.26710(9) 0.84102(17) 0.0565(6) Uani 1 1 d . . .
H3A H 1.1229 0.2812 0.8341 0.085 Uiso 1 1 calc R . .
O4 O 0.77738(14) 0.35268(10) 0.7480(2) 0.0733(7) Uani 1 1 d . . .
O5 O 0.41623(12) 0.23114(9) 0.61948(18) 0.0585(6) Uani 1 1 d . . .
H5A H 0.4376 0.2408 0.5514 0.088 Uiso 1 1 calc R . .
O6 O 0.42295(12) 0.24616(9) 0.85081(17) 0.0550(5) Uani 1 1 d . . .
H6A H 0.3796 0.2293 0.8370 0.083 Uiso 1 1 calc R . .
O7 O 0.54820(13) 0.47755(9) 0.7991(2) 0.0684(6) Uani 1 1 d . . .
O8 O 0.22232(12) 0.32371(9) 0.83800(17) 0.0530(5) Uani 1 1 d . . .
H8 H 0.2455 0.3351 0.9089 0.080 Uiso 1 1 calc R . .
O9 O 0.23690(12) 0.31962(9) 0.60719(17) 0.0541(5) Uani 1 1 d . . .
H9 H 0.2003 0.2974 0.6158 0.081 Uiso 1 1 calc R . .
O10 O -0.05260(15) 0.46875(10) 0.2046(3) 0.0798(7) Uani 1 1 d . . .
O11 O 0.28075(12) 0.31694(9) 0.33929(17) 0.0527(5) Uani 1 1 d . . .
H11A H 0.2580 0.3265 0.4062 0.079 Uiso 1 1 calc R . .
O12 O 0.27542(12) 0.32990(9) 0.10758(17) 0.0552(5) Uani 1 1 d . . .
H12A H 0.3178 0.3120 0.1223 0.083 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O3 1.363(3) . ?
B1 O2 1.370(3) . ?
B1 C1 1.548(4) . ?
B2 O5 1.368(4) . ?
B2 O6 1.370(3) . ?
B2 C10 1.543(4) . ?
B3 O8 1.358(3) . ?
B3 O9 1.379(3) . ?
B3 C19 1.551(4) . ?
B4 O12 1.362(3) . ?
B4 O11 1.365(3) . ?
B4 C28 1.555(4) . ?
C1 C2 1.389(4) . ?
C1 C6 1.394(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.379(4) . ?
C4 C5 1.366(4) . ?
C4 O1 1.367(3) . ?
C5 C6 1.374(4) . ?
C7 O1 1.408(4) . ?
C7 C8 1.511(5) . ?
C8 C9 1.467(5) . ?
C10 C11 1.387(4) . ?
C10 C15 1.398(4) . ?
C11 C12 1.380(4) . ?
C12 C13 1.372(4) . ?
C13 O4 1.372(3) . ?
C13 C14 1.374(4) . ?
C14 C15 1.373(4) . ?
C16 O4 1.422(4) . ?
C16 C17 1.519(5) . ?
C17 C18 1.413(6) . ?
C19 C20 1.390(4) . ?
C19 C24 1.396(4) . ?
C20 C21 1.384(4) . ?
C21 C22 1.381(4) . ?
C22 O7 1.362(3) . ?
C22 C23 1.383(4) . ?
C23 C24 1.373(4) . ?
C25 O7 1.424(4) . ?
C25 C26 1.511(5) . ?
C26 C27 1.518(6) . ?
C28 C33 1.378(4) . ?
C28 C29 1.404(4) . ?
C29 C30 1.366(4) . ?
C30 C31 1.367(4) . ?
C31 C32 1.373(4) . ?
C31 O10 1.375(4) . ?
C32 C33 1.385(4) . ?
C37 O10 1.404(4) . ?
C37 C38 1.500(5) . ?
C38 C39 1.516(6) . ?

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
O3 B1 O2 115.9(2) . . ?
O3 B1 C1 120.0(2) . . ?
O2 B1 C1 124.0(2) . . ?
O5 B2 O6 115.8(3) . . ?
O5 B2 C10 124.0(2) . . ?
O6 B2 C10 120.2(2) . . ?
O8 B3 O9 116.1(3) . . ?
O8 B3 C19 124.1(2) . . ?
O9 B3 C19 119.8(2) . . ?
O12 B4 O11 116.2(3) . . ?
O12 B4 C28 119.3(2) . . ?
O11 B4 C28 124.4(2) . . ?
C2 C1 C6 115.6(3) . . ?
C2 C1 B1 121.4(2) . . ?
C6 C1 B1 123.0(2) . . ?
C3 C2 C1 123.0(3) . . ?
C2 C3 C4 119.3(3) . . ?
C5 C4 O1 116.4(3) . . ?
C5 C4 C3 119.4(3) . . ?
O1 C4 C3 124.2(3) . . ?
C4 C5 C6 120.6(3) . . ?
C5 C6 C1 122.1(3) . . ?
O1 C7 C8 108.5(3) . . ?
C9 C8 C7 112.1(4) . . ?
C11 C10 C15 115.6(3) . . ?
C11 C10 B2 122.4(3) . . ?
C15 C10 B2 121.9(2) . . ?
C12 C11 C10 123.0(3) . . ?
C13 C12 C11 119.5(3) . . ?
C12 C13 O4 124.5(3) . . ?
C12 C13 C14 119.4(3) . . ?
O4 C13 C14 116.1(3) . . ?
C15 C14 C13 120.5(3) . . ?
C14 C15 C10 122.0(3) . . ?
O4 C16 C17 109.4(3) . . ?
C18 C17 C16 113.7(4) . . ?
C20 C19 C24 116.0(3) . . ?
C20 C19 B3 122.6(2) . . ?
C24 C19 B3 121.5(2) . . ?
C21 C20 C19 122.6(3) . . ?
C22 C21 C20 119.6(3) . . ?
O7 C22 C21 125.0(3) . . ?
O7 C22 C23 115.7(3) . . ?
C21 C22 C23 119.3(3) . . ?
C24 C23 C22 120.1(3) . . ?
C23 C24 C19 122.4(3) . . ?
O7 C25 C26 107.0(3) . . ?
C25 C26 C27 113.7(3) . . ?
C33 C28 C29 115.6(3) . . ?
C33 C28 B4 123.1(3) . . ?
C29 C28 B4 121.2(2) . . ?
C30 C29 C28 122.3(3) . . ?
C29 C30 C31 120.3(3) . . ?
C30 C31 C32 119.6(3) . . ?
C30 C31 O10 115.8(3) . . ?
C32 C31 O10 124.6(3) . . ?
C31 C32 C33 119.6(3) . . ?
C28 C33 C32 122.6(3) . . ?
O10 C37 C38 108.8(3) . . ?
C37 C38 C39 109.8(4) . . ?
C4 O1 C7 119.3(2) . . ?
C13 O4 C16 118.3(2) . . ?
C22 O7 C25 118.8(2) . . ?
C31 O10 C37 117.3(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
O3 B1 C1 C2 17.9(4) . . . . ?
O2 B1 C1 C2 -160.3(3) . . . . ?
O3 B1 C1 C6 -164.3(3) . . . . ?
O2 B1 C1 C6 17.6(5) . . . . ?
C6 C1 C2 C3 -1.3(5) . . . . ?
B1 C1 C2 C3 176.7(3) . . . . ?
C1 C2 C3 C4 2.2(5) . . . . ?
C2 C3 C4 C5 -1.8(5) . . . . ?
C2 C3 C4 O1 178.8(3) . . . . ?
O1 C4 C5 C6 -179.9(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
B1 C1 C6 C5 -177.9(3) . . . . ?
O1 C7 C8 C9 174.7(4) . . . . ?
O5 B2 C10 C11 -16.9(5) . . . . ?
O6 B2 C10 C11 160.4(3) . . . . ?
O5 B2 C10 C15 166.3(3) . . . . ?
O6 B2 C10 C15 -16.4(4) . . . . ?
C15 C10 C11 C12 2.9(5) . . . . ?
B2 C10 C11 C12 -174.2(3) . . . . ?
C10 C11 C12 C13 -1.4(5) . . . . ?
C11 C12 C13 O4 178.6(3) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
O4 C13 C14 C15 -178.3(3) . . . . ?
C13 C14 C15 C10 0.5(5) . . . . ?
C11 C10 C15 C14 -2.4(4) . . . . ?
B2 C10 C15 C14 174.7(3) . . . . ?
O4 C16 C17 C18 -63.0(5) . . . . ?
O8 B3 C19 C20 171.0(3) . . . . ?
O9 B3 C19 C20 -10.5(4) . . . . ?
O8 B3 C19 C24 -9.6(4) . . . . ?
O9 B3 C19 C24 168.9(3) . . . . ?
C24 C19 C20 C21 0.8(4) . . . . ?
B3 C19 C20 C21 -179.7(3) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C21 C22 O7 178.7(3) . . . . ?
C20 C21 C22 C23 -0.8(5) . . . . ?
O7 C22 C23 C24 -178.6(3) . . . . ?
C21 C22 C23 C24 1.0(5) . . . . ?
C22 C23 C24 C19 -0.3(5) . . . . ?
C20 C19 C24 C23 -0.6(4) . . . . ?
B3 C19 C24 C23 179.8(3) . . . . ?
O7 C25 C26 C27 61.9(4) . . . . ?
O12 B4 C28 C33 175.5(3) . . . . ?
O11 B4 C28 C33 -3.9(5) . . . . ?
O12 B4 C28 C29 -5.0(4) . . . . ?
O11 B4 C28 C29 175.6(3) . . . . ?
C33 C28 C29 C30 -0.2(5) . . . . ?
B4 C28 C29 C30 -179.7(3) . . . . ?
C28 C29 C30 C31 -1.4(5) . . . . ?
C29 C30 C31 C32 2.1(5) . . . . ?
C29 C30 C31 O10 -178.0(3) . . . . ?
C30 C31 C32 C33 -1.1(5) . . . . ?
O10 C31 C32 C33 178.9(3) . . . . ?
C29 C28 C33 C32 1.1(5) . . . . ?
B4 C28 C33 C32 -179.3(3) . . . . ?
C31 C32 C33 C28 -0.5(5) . . . . ?
O10 C37 C38 C39 178.7(4) . . . . ?
C5 C4 O1 C7 -179.8(3) . . . . ?
C3 C4 O1 C7 -0.4(5) . . . . ?
C8 C7 O1 C4 179.9(3) . . . . ?
C12 C13 O4 C16 0.7(5) . . . . ?
C14 C13 O4 C16 -179.9(3) . . . . ?
C17 C16 O4 C13 -171.3(3) . . . . ?
C21 C22 O7 C25 -7.3(5) . . . . ?
C23 C22 O7 C25 172.2(3) . . . . ?
C26 C25 O7 C22 -171.7(3) . . . . ?
C30 C31 O10 C37 171.3(3) . . . . ?
C32 C31 O10 C37 -8.8(5) . . . . ?
C38 C37 O10 C31 -173.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O8 0.82 1.92 2.735(3) 170.2 1_655
O11 H11A O9 0.82 2.06 2.807(2) 151.7 .
O8 H8 O12 0.82 2.00 2.746(2) 151.9 1_556
O9 H9 O2 0.82 1.97 2.770(3) 165.7 1_455
O5 H5A O6 0.82 2.01 2.735(2) 147.0 4_565
O6 H6A O11 0.82 1.97 2.781(3) 168.8 4_566

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_6_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1547338'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H7 B O2'
_chemical_formula_weight         121.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Iba2

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

_cell_length_a                   15.322(3)
_cell_length_b                   17.902(3)
_cell_length_c                   9.8089(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2690.5(8)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    61
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      26.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9771
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8649
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         26.49
_reflns_number_total             2722
_reflns_number_gt                2112
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0396P)²+0.1693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0071(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_number_reflns         2722
_refine_ls_number_parameters     168
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.20895(12) 0.99500(10) 0.0785(2) 0.0481(4) Uani 1 1 d . . .
B2 B 0.99208(12) 0.13239(10) 0.03953(19) 0.0448(4) Uani 1 1 d . . .
C1 C 0.29561(11) 0.94989(9) 0.08144(19) 0.0516(4) Uani 1 1 d . . .
C2 C 0.35581(13) 0.96074(11) 0.1861(2) 0.0746(6) Uani 1 1 d . . .
H2 H 0.3436 0.9947 0.2553 0.090 Uiso 1 1 calc R . .
C3 C 0.43388(15) 0.92139(14) 0.1881(3) 0.0928(8) Uani 1 1 d . . .
H3 H 0.4736 0.9294 0.2583 0.111 Uiso 1 1 calc R . .
C4 C 0.45273(15) 0.87118(13) 0.0882(3) 0.0903(8) Uani 1 1 d . . .
H4 H 0.5055 0.8456 0.0895 0.108 Uiso 1 1 calc R . .
C5 C 0.39409(16) 0.85853(13) -0.0136(3) 0.0860(7) Uani 1 1 d . . .
H5 H 0.4063 0.8234 -0.0808 0.103 Uiso 1 1 calc R . .
C6 C 0.31676(14) 0.89775(11) -0.0172(2) 0.0692(5) Uani 1 1 d . . .
H6 H 0.2777 0.8889 -0.0879 0.083 Uiso 1 1 calc R . .
C7 C 0.91943(10) 0.19264(9) 0.03393(18) 0.0486(4) Uani 1 1 d . . .
C8 C 0.90142(12) 0.23067(10) -0.0864(2) 0.0641(5) Uani 1 1 d . . .
H8 H 0.9323 0.2182 -0.1647 0.077 Uiso 1 1 calc R . .
C9 C 0.83930(15) 0.28621(12) -0.0935(3) 0.0805(6) Uani 1 1 d . . .
H9 H 0.8286 0.3105 -0.1756 0.097 Uiso 1 1 calc R . .
C10 C 0.79355(15) 0.30534(12) 0.0210(3) 0.0846(7) Uani 1 1 d . . .
H10 H 0.7515 0.3427 0.0169 0.101 Uiso 1 1 calc R . .
C11 C 0.80965(14) 0.26965(13) 0.1412(3) 0.0824(7) Uani 1 1 d . . .
H11 H 0.7787 0.2830 0.2191 0.099 Uiso 1 1 calc R . .
C12 C 0.87164(12) 0.21387(11) 0.1478(2) 0.0647(5) Uani 1 1 d . . .
H12 H 0.8817 0.1899 0.2305 0.078 Uiso 1 1 calc R . .
O1 O 0.16091(7) 1.00686(7) -0.03574(12) 0.0586(3) Uani 1 1 d . . .
H1 H 0.1883 0.9924 -0.1026 0.088 Uiso 1 1 calc R . .
O2 O 0.17829(8) 1.02693(7) 0.19490(11) 0.0595(3) Uani 1 1 d . . .
H2A H 0.1313 1.0472 0.1794 0.089 Uiso 1 1 calc R . .
O3 O 1.03242(8) 0.11116(7) -0.07883(11) 0.0575(3) Uani 1 1 d . . .
H3A H 1.0687 0.0787 -0.0622 0.086 Uiso 1 1 calc R . .
O4 O 1.02138(8) 0.09897(7) 0.15506(11) 0.0554(3) Uani 1 1 d . . .
H4A H 0.9956 0.1163 0.2211 0.083 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.357(2) . ?
B1 O2 1.360(2) . ?
B1 C1 1.554(2) . ?
B2 O4 1.358(2) . ?
B2 O3 1.369(2) . ?
B2 C7 1.551(2) . ?
C1 C6 1.383(3) . ?
C1 C2 1.394(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.361(4) . ?
C4 C5 1.363(4) . ?
C5 C6 1.378(3) . ?
C7 C12 1.389(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.367(4) . ?
C10 C11 1.364(4) . ?
C11 C12 1.380(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
O1 B1 O2 116.09(14) . . ?
O1 B1 C1 124.04(16) . . ?
O2 B1 C1 119.85(16) . . ?
O4 B2 O3 115.86(14) . . ?
O4 B2 C7 124.98(15) . . ?
O3 B2 C7 119.14(15) . . ?
C6 C1 C2 117.03(17) . . ?
C6 C1 B1 122.54(16) . . ?
C2 C1 B1 120.43(16) . . ?
C3 C2 C1 120.7(2) . . ?
C4 C3 C2 120.5(2) . . ?
C3 C4 C5 119.9(2) . . ?
C4 C5 C6 120.1(2) . . ?
C5 C6 C1 121.8(2) . . ?
C12 C7 C8 116.37(16) . . ?
C12 C7 B2 122.70(16) . . ?
C8 C7 B2 120.88(16) . . ?
C9 C8 C7 122.2(2) . . ?
C10 C9 C8 119.5(2) . . ?
C11 C10 C9 120.01(19) . . ?
C10 C11 C12 120.3(2) . . ?
C11 C12 C7 121.5(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
O1 B1 C1 C6 -22.4(3) . . . . ?
O2 B1 C1 C6 159.28(18) . . . . ?
O1 B1 C1 C2 157.83(18) . . . . ?
O2 B1 C1 C2 -20.5(3) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
B1 C1 C2 C3 -179.1(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
B1 C1 C6 C5 179.60(19) . . . . ?
O4 B2 C7 C12 -5.6(3) . . . . ?
O3 B2 C7 C12 175.87(17) . . . . ?
O4 B2 C7 C8 171.64(16) . . . . ?
O3 B2 C7 C8 -6.9(2) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
B2 C7 C8 C9 -177.80(17) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C7 0.3(3) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
B2 C7 C12 C11 177.48(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O3 0.82 2.01 2.7460(15) 148.9 8_645
O3 H3A O1 0.82 1.93 2.7460(17) 174.5 1_645
O2 H2A O4 0.82 1.94 2.7560(16) 175.9 1_465
O1 H1 O2 0.82 2.02 2.7235(16) 143.2 7_464

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.088
_refine_diff_density_rms         0.022
####################################################################### 
# 
# 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_190920czp_0m
_database_code_depnum_ccdc_archive 'CCDC 1547361'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H9 B O3'
_chemical_formula_weight         151.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   11.2586(15)
_cell_length_b                   5.0616(7)
_cell_length_c                   13.8819(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.069(2)
_cell_angle_gamma                90.00
_cell_volume                     738.20(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    59
_cell_measurement_theta_min      7.5
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9697
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4509
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         26.49
_reflns_number_total             1524
_reflns_number_gt                1359
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0450P)²+0.2149P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.086(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1524
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.79639(12) -0.0643(3) 0.40880(9) 0.0307(3) Uani 1 1 d . . .
C1 C 0.84249(10) -0.0291(2) 0.52843(8) 0.0294(3) Uani 1 1 d . . .
C2 C 0.80007(12) 0.1758(2) 0.57480(9) 0.0352(3) Uani 1 1 d . . .
H2 H 0.7429 0.2978 0.5330 0.042 Uiso 1 1 calc R . .
C3 C 0.84008(12) 0.2046(2) 0.68124(9) 0.0374(3) Uani 1 1 d . . .
H3 H 0.8085 0.3411 0.7100 0.045 Uiso 1 1 calc R . .
C4 C 0.92755(11) 0.0274(2) 0.74397(8) 0.0331(3) Uani 1 1 d . . .
C5 C 0.97235(11) -0.1784(2) 0.70021(9) 0.0361(3) Uani 1 1 d . . .
H5 H 1.0311 -0.2976 0.7423 0.043 Uiso 1 1 calc R . .
C6 C 0.92972(11) -0.2057(2) 0.59457(9) 0.0331(3) Uani 1 1 d . . .
H6 H 0.9598 -0.3456 0.5663 0.040 Uiso 1 1 calc R . .
C7 C 0.93240(17) 0.2491(3) 0.89691(10) 0.0544(4) Uani 1 1 d . . .
H7A H 0.9565 0.4144 0.8754 0.082 Uiso 1 1 calc R . .
H7B H 0.9707 0.2337 0.9706 0.082 Uiso 1 1 calc R . .
H7C H 0.8415 0.2416 0.8766 0.082 Uiso 1 1 calc R . .
O1 O 0.97474(10) 0.0374(2) 0.84963(6) 0.0470(3) Uani 1 1 d . . .
O2 O 0.80626(9) -0.30584(16) 0.36986(6) 0.0406(3) Uani 1 1 d . . .
H2A H 0.7910 -0.2933 0.3077 0.061 Uiso 1 1 calc R . .
O3 O 0.74395(9) 0.13751(17) 0.34118(6) 0.0395(3) Uani 1 1 d . . .
H3A H 0.7537 0.2773 0.3730 0.059 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O2 1.3575(16) . ?
B1 O3 1.3691(15) . ?
B1 C1 1.5618(16) . ?
C1 C2 1.3924(16) . ?
C1 C6 1.3994(16) . ?
C2 C3 1.3889(16) . ?
C3 C4 1.3842(17) . ?
C4 O1 1.3697(13) . ?
C4 C5 1.3885(17) . ?
C5 C6 1.3763(16) . ?
C7 O1 1.4251(17) . ?

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
O2 B1 O3 118.41(10) . . ?
O2 B1 C1 118.86(10) . . ?
O3 B1 C1 122.72(11) . . ?
C2 C1 C6 116.67(10) . . ?
C2 C1 B1 122.57(10) . . ?
C6 C1 B1 120.75(10) . . ?
C3 C2 C1 122.41(11) . . ?
C4 C3 C2 119.12(11) . . ?
O1 C4 C3 124.34(11) . . ?
O1 C4 C5 115.73(11) . . ?
C3 C4 C5 119.93(10) . . ?
C6 C5 C4 119.95(11) . . ?
C5 C6 C1 121.90(11) . . ?
C4 O1 C7 117.11(10) . . ?

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
O2 B1 C1 C2 -158.32(12) . . . . ?
O3 B1 C1 C2 20.37(18) . . . . ?
O2 B1 C1 C6 21.65(16) . . . . ?
O3 B1 C1 C6 -159.66(12) . . . . ?
C6 C1 C2 C3 -0.79(18) . . . . ?
B1 C1 C2 C3 179.18(11) . . . . ?
C1 C2 C3 C4 1.53(19) . . . . ?
C2 C3 C4 O1 179.38(11) . . . . ?
C2 C3 C4 C5 -1.11(18) . . . . ?
O1 C4 C5 C6 179.56(11) . . . . ?
C3 C4 C5 C6 0.01(18) . . . . ?
C4 C5 C6 C1 0.75(19) . . . . ?
C2 C1 C6 C5 -0.36(17) . . . . ?
B1 C1 C6 C5 179.67(11) . . . . ?
C3 C4 O1 C7 -1.59(19) . . . . ?
C5 C4 O1 C7 178.88(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_czf-6
_database_code_depnum_ccdc_archive 'CCDC 1547294'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H15 B O3'
_chemical_formula_weight         194.03

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.0709(3)
_cell_length_b                   7.6864(7)
_cell_length_c                   13.7993(11)
_cell_angle_alpha                87.907(7)
_cell_angle_beta                 85.499(6)
_cell_angle_gamma                74.195(7)
_cell_volume                     515.86(7)
_cell_formula_units_Z            2
_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    1.249
_exptl_crystal_F_000             208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.722
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_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            3611
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.213
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1834
_reflns_number_gt                1553
_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    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0520P)²+0.1600P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1834
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_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
O2 O 0.25352(19) 0.59451(14) 0.42172(7) 0.0183(3) Uani 1 1 d . . . . .
H2 H 0.1164 0.6079 0.3914 0.027 Uiso 1 1 calc R U . . .
O3 O 0.72744(19) 0.55439(15) 0.39398(7) 0.0193(3) Uani 1 1 d . . . . .
H3 H 0.7165 0.5135 0.4494 0.029 Uiso 1 1 calc R U . . .
O6 O 0.36748(19) 0.82150(14) -0.04147(7) 0.0180(3) Uani 1 1 d . . . . .
C1 C 0.4459(3) 0.6565(2) 0.24911(10) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.1810(3) 0.8208(2) 0.11867(10) 0.0164(3) Uani 1 1 d . . . . .
H3A H 0.0174 0.8961 0.0983 0.020 Uiso 1 1 calc R U . . .
C6 C 0.6679(3) 0.59955(19) 0.18023(10) 0.0155(3) Uani 1 1 d . . . . .
H6 H 0.8327 0.5259 0.2006 0.019 Uiso 1 1 calc R U . . .
C7 C 0.4073(3) 0.76126(19) 0.05187(10) 0.0150(3) Uani 1 1 d . . . . .
C10 C 0.4951(3) 0.8532(2) -0.20861(10) 0.0168(3) Uani 1 1 d . . . . .
H10A H 0.4310 0.9834 -0.2019 0.020 Uiso 1 1 calc R U . . .
H10B H 0.3409 0.8103 -0.2246 0.020 Uiso 1 1 calc R U . . .
C11 C 0.2019(3) 0.76727(19) 0.21501(10) 0.0157(3) Uani 1 1 d . . . . .
H11 H 0.0493 0.8059 0.2587 0.019 Uiso 1 1 calc R U . . .
C13 C 0.6514(3) 0.6489(2) 0.08276(10) 0.0161(3) Uani 1 1 d . . . . .
H13 H 0.8019 0.6073 0.0386 0.019 Uiso 1 1 calc R U . . .
C16 C 0.5953(3) 0.7687(2) -0.11305(10) 0.0159(3) Uani 1 1 d . . . . .
H16A H 0.6560 0.6381 -0.1179 0.019 Uiso 1 1 calc R U . . .
H16B H 0.7481 0.8114 -0.0954 0.019 Uiso 1 1 calc R U . . .
C18 C 0.7193(3) 0.8082(2) -0.29112(10) 0.0199(3) Uani 1 1 d . . . . .
H18A H 0.7915 0.6779 -0.2949 0.024 Uiso 1 1 calc R U . . .
H18B H 0.8684 0.8577 -0.2769 0.024 Uiso 1 1 calc R U . . .
C2 C 0.6156(4) 0.8828(2) -0.38900(11) 0.0290(4) Uani 1 1 d . . . . .
H2A H 0.7633 0.8504 -0.4386 0.044 Uiso 1 1 calc R U . . .
H2B H 0.5488 1.0122 -0.3862 0.044 Uiso 1 1 calc R U . . .
H2C H 0.4696 0.8330 -0.4039 0.044 Uiso 1 1 calc R U . . .
B3 B 0.4742(3) 0.6002(2) 0.35814(12) 0.0157(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
O2 B3 1.3762(18) . ?
O2 H2 0.8200 . ?
O3 B3 1.3631(19) . ?
O3 H3 0.8200 . ?
O6 C7 1.3640(17) . ?
O6 C16 1.4387(16) . ?
C1 C6 1.3986(19) . ?
C1 C11 1.402(2) . ?
C1 B3 1.557(2) . ?
C3 C11 1.381(2) . ?
C3 C7 1.3981(19) . ?
C3 H3A 0.9300 . ?
C6 C13 1.387(2) . ?
C6 H6 0.9300 . ?
C7 C13 1.391(2) . ?
C10 C16 1.5107(19) . ?
C10 C18 1.5230(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C2 1.523(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B3 O2 H2 109.5 . . ?
B3 O3 H3 109.5 . . ?
C7 O6 C16 117.96(11) . . ?
C6 C1 C11 116.69(13) . . ?
C6 C1 B3 120.83(13) . . ?
C11 C1 B3 122.47(13) . . ?
C11 C3 C7 119.60(13) . . ?
C11 C3 H3A 120.2 . . ?
C7 C3 H3A 120.2 . . ?
C13 C6 C1 122.44(13) . . ?
C13 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
O6 C7 C13 124.69(13) . . ?
O6 C7 C3 115.40(12) . . ?
C13 C7 C3 119.91(13) . . ?
C16 C10 C18 112.08(12) . . ?
C16 C10 H10A 109.2 . . ?
C18 C10 H10A 109.2 . . ?
C16 C10 H10B 109.2 . . ?
C18 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C3 C11 C1 122.09(13) . . ?
C3 C11 H11 119.0 . . ?
C1 C11 H11 119.0 . . ?
C6 C13 C7 119.24(13) . . ?
C6 C13 H13 120.4 . . ?
C7 C13 H13 120.4 . . ?
O6 C16 C10 106.79(11) . . ?
O6 C16 H16A 110.4 . . ?
C10 C16 H16A 110.4 . . ?
O6 C16 H16B 110.4 . . ?
C10 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C10 C18 C2 112.52(12) . . ?
C10 C18 H18A 109.1 . . ?
C2 C18 H18A 109.1 . . ?
C10 C18 H18B 109.1 . . ?
C2 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C2 H2A 109.5 . . ?
C18 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C18 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 B3 O2 117.38(13) . . ?
O3 B3 C1 119.52(13) . . ?
O2 B3 C1 123.10(13) . . ?

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
C11 C1 C6 C13 0.0(2) . . . . ?
B3 C1 C6 C13 -179.14(13) . . . . ?
C16 O6 C7 C13 -1.4(2) . . . . ?
C16 O6 C7 C3 178.35(12) . . . . ?
C11 C3 C7 O6 -179.84(12) . . . . ?
C11 C3 C7 C13 0.0(2) . . . . ?
C7 C3 C11 C1 1.1(2) . . . . ?
C6 C1 C11 C3 -1.1(2) . . . . ?
B3 C1 C11 C3 178.08(13) . . . . ?
C1 C6 C13 C7 1.0(2) . . . . ?
O6 C7 C13 C6 178.81(13) . . . . ?
C3 C7 C13 C6 -1.0(2) . . . . ?
C7 O6 C16 C10 -179.99(12) . . . . ?
C18 C10 C16 O6 179.67(11) . . . . ?
C16 C10 C18 C2 176.41(13) . . . . ?
C6 C1 B3 O3 23.9(2) . . . . ?
C11 C1 B3 O3 -155.16(14) . . . . ?
C6 C1 B3 O2 -156.27(14) . . . . ?
C11 C1 B3 O2 24.6(2) . . . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.074

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_20161031b
_database_code_depnum_ccdc_archive 'CCDC 1547292'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_audit_creation_date             2016-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 B O3'
_chemical_formula_sum            'C8 H11 B O3'
_chemical_formula_weight         165.98
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1B1O1
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'
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_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                   19.8150(4)
_cell_length_b                   5.02009(8)
_cell_length_c                   18.2337(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.493(2)
_cell_angle_gamma                90
_cell_volume                     1687.63(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4079
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.1180
_cell_measurement_theta_min      4.7910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (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    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0110
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5054
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.250
_diffrn_reflns_theta_min         4.797
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  51.00   1.00    1.00    --   41.62 -37.00-150.00   35
  2  ω     27.00  96.00   1.00    1.00    --   41.62-125.00-150.00   69
  3  ω     35.00 128.00   1.00    1.00    --  107.19 -45.00-180.00   93
  4  ω    107.00 175.00   1.00    1.00    --  107.19  30.00 -90.00   68
  5  ω    132.00 177.00   1.00    1.00    --  107.19  45.00-150.00   45
  6  ω    133.00 163.00   1.00    1.00    --  107.19 125.00-120.00   30
  7  ω     97.00 134.00   1.00    1.00    --  107.19 125.00 -90.00   37
  8  ω     79.00 178.00   1.00    1.00    --  107.19  30.00   0.00   99
  9  ω     75.00 133.00   1.00    1.00    --  107.19 -61.00 -30.00   58
 10  ω     59.00 120.00   1.00    1.00    --  107.19-125.00   0.00   61
 11  ω     48.00  80.00   1.00    1.00    --  107.19 -45.00 -30.00   32
 12  ω     36.00  65.00   1.00    1.00    --  107.19 -61.00 -30.00   29
 13  ω     26.00 102.00   1.00    1.00    --  107.19 -94.00-150.00   76
 14  ω     40.00 115.00   1.00    1.00    --  107.19-125.00-150.00   75
 15  ω     32.00  75.00   1.00    1.00    --   41.62-125.00  30.00   43
 16  ω     43.00  72.00   1.00    1.00    --   41.62-125.00  60.00   29
 17  ω   -129.00  47.00   1.00    1.00    --  -41.62   0.00 120.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0757573000
_diffrn_orient_matrix_UB_12      -0.0217877000
_diffrn_orient_matrix_UB_13      -0.0049927000
_diffrn_orient_matrix_UB_21      0.0272718000
_diffrn_orient_matrix_UB_22      -0.1563137000
_diffrn_orient_matrix_UB_23      0.0781194000
_diffrn_orient_matrix_UB_31      -0.0224279000
_diffrn_orient_matrix_UB_32      -0.2630318000
_diffrn_orient_matrix_UB_33      -0.0460856000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1592
_reflns_number_total             1666
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_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         0.333
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+1.2597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0877
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68307(4) 0.54596(16) 0.18640(4) 0.0221(2) Uani 1 1 d . . . . .
O2 O 0.51834(4) 0.72158(14) 0.43964(4) 0.01809(19) Uani 1 1 d . . . . .
H2 H 0.5298 0.8601 0.4234 0.027 Uiso 1 1 calc GR . . . .
O3 O 0.54915(4) 0.26929(14) 0.45281(4) 0.01847(19) Uani 1 1 d . . . . .
H3 H 0.5296 0.2873 0.4851 0.028 Uiso 1 1 calc GR . . . .
C1 C 0.70465(6) 0.6820(3) 0.07254(7) 0.0292(3) Uani 1 1 d . . . . .
H1A H 0.6940 0.8142 0.0318 0.044 Uiso 1 1 calc GR . . . .
H1B H 0.6897 0.5101 0.0492 0.044 Uiso 1 1 calc GR . . . .
H1C H 0.7559 0.6803 0.1024 0.044 Uiso 1 1 calc GR . . . .
C2 C 0.66430(6) 0.7475(3) 0.12644(6) 0.0251(3) Uani 1 1 d . . . . .
H2A H 0.6784 0.9219 0.1499 0.030 Uiso 1 1 calc R . . . .
H2B H 0.6124 0.7477 0.0971 0.030 Uiso 1 1 calc R . . . .
C3 C 0.65004(5) 0.5544(2) 0.24033(6) 0.0173(2) Uani 1 1 d . . . . .
C4 C 0.59944(6) 0.7448(2) 0.24131(6) 0.0175(2) Uani 1 1 d . . . . .
H4 H 0.5858 0.8796 0.2037 0.021 Uiso 1 1 calc R . . . .
C5 C 0.56938(5) 0.7311(2) 0.29939(6) 0.0164(2) Uani 1 1 d . . . . .
H5 H 0.5359 0.8598 0.3002 0.020 Uiso 1 1 calc R . . . .
C6 C 0.58778(5) 0.5307(2) 0.35621(6) 0.0148(2) Uani 1 1 d . . . . .
C7 C 0.63909(6) 0.3421(2) 0.35350(6) 0.0187(2) Uani 1 1 d . . . . .
H7 H 0.6524 0.2060 0.3907 0.022 Uiso 1 1 calc R . . . .
C8 C 0.67029(6) 0.3532(2) 0.29710(6) 0.0205(2) Uani 1 1 d . . . . .
H8 H 0.7046 0.2272 0.2970 0.025 Uiso 1 1 calc R . . . .
B1 B 0.55092(6) 0.5093(2) 0.41820(6) 0.0150(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.4350(13) . ?
O1 C3 1.3671(12) . ?
O2 H2 0.8200 . ?
O2 B1 1.3749(13) . ?
O3 H3 0.8200 . ?
O3 B1 1.3664(13) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.5131(15) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.3899(15) . ?
C3 C8 1.3958(15) . ?
C4 H4 0.9300 . ?
C4 C5 1.3942(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.3931(14) . ?
C6 C7 1.4033(14) . ?
C6 B1 1.5582(14) . ?
C7 H7 0.9300 . ?
C7 C8 1.3816(14) . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 117.86(8) . . ?
B1 O2 H2 109.5 . . ?
B1 O3 H3 109.5 . . ?
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 C1 106.90(9) . . ?
O1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
O1 C3 C4 124.63(9) . . ?
O1 C3 C8 115.31(9) . . ?
C4 C3 C8 120.06(9) . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.12(9) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.17(9) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C7 117.16(9) . . ?
C5 C6 B1 121.66(9) . . ?
C7 C6 B1 121.13(9) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.77(10) . . ?
C8 C7 H7 119.1 . . ?
C3 C8 H8 120.1 . . ?
C7 C8 C3 119.71(10) . . ?
C7 C8 H8 120.1 . . ?
O2 B1 C6 123.11(9) . . ?
O3 B1 O2 117.26(9) . . ?
O3 B1 C6 119.62(9) . . ?

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
O1 C3 C4 C5 179.74(9) . . . . ?
O1 C3 C8 C7 -179.00(9) . . . . ?
C2 O1 C3 C4 -0.03(15) . . . . ?
C2 O1 C3 C8 179.87(9) . . . . ?
C3 O1 C2 C1 -176.65(9) . . . . ?
C3 C4 C5 C6 -0.69(16) . . . . ?
C4 C3 C8 C7 0.91(16) . . . . ?
C4 C5 C6 C7 0.76(15) . . . . ?
C4 C5 C6 B1 -176.87(9) . . . . ?
C5 C6 C7 C8 0.02(15) . . . . ?
C5 C6 B1 O2 -22.82(15) . . . . ?
C5 C6 B1 O3 156.10(10) . . . . ?
C6 C7 C8 C3 -0.84(17) . . . . ?
C7 C6 B1 O2 159.66(10) . . . . ?
C7 C6 B1 O3 -21.43(14) . . . . ?
C8 C3 C4 C5 -0.16(16) . . . . ?
B1 C6 C7 C8 177.65(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.752
####################################################################### 
# 
# 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_20161108c
_database_code_depnum_ccdc_archive 'CCDC 1547297'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_audit_creation_date             2016-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 B3 F3 O3'
_chemical_formula_sum            'C18 H12 B3 F3 O3'
_chemical_formula_weight         365.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1b1o1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   3.8105(3)
_cell_length_b                   20.8028(16)
_cell_length_c                   10.3896(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.843(8)
_cell_angle_gamma                90
_cell_volume                     817.71(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3121
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.8320
_cell_measurement_theta_min      4.0980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (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    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2051
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.863
_diffrn_reflns_theta_min         3.540
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00 -19.00   1.00    5.00    --   12.76 -37.00  30.00   27
  2  ω    -44.00  54.00   1.00    5.00    --   12.76 -19.00   0.00   98
  3  ω     22.00  51.00   1.00    5.00    --   12.76 -99.00   0.00   29
  4  ω    -18.00  24.00   1.00    5.00    --  -11.04 -99.00-180.00   42
  5  ω    -45.00  25.00   1.00    5.00    --   12.76 -77.00 -60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0274895000
_diffrn_orient_matrix_UB_12      0.0295384000
_diffrn_orient_matrix_UB_13      -0.0109605000
_diffrn_orient_matrix_UB_21      0.0102464000
_diffrn_orient_matrix_UB_22      0.0161678000
_diffrn_orient_matrix_UB_23      0.0201269000
_diffrn_orient_matrix_UB_31      0.1837904000
_diffrn_orient_matrix_UB_32      -0.0053386000
_diffrn_orient_matrix_UB_33      0.0004636000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1528
_reflns_number_total             2051
_reflns_odcompleteness_completeness 98.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 _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 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_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         0.311
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.078
_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)+(0.0552P)²+0.0158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1308
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.878(3) 0.122(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
B1 B 0.3120(4) 0.19214(8) 0.59900(18) 0.0157(4) Uani 1 1 d . . . . .
B2 B -0.0111(6) 0.2500 0.4224(3) 0.0160(5) Uani 1 2 d S T P . .
C1 C 0.6121(4) 0.01450(7) 0.79426(16) 0.0203(4) Uani 1 1 d . . . . .
C2 C 0.7168(4) 0.07139(7) 0.85498(15) 0.0187(4) Uani 1 1 d . . . . .
H2 H 0.8467 0.0717 0.9366 0.022 Uiso 1 1 calc R . . . .
C3 C 0.6216(4) 0.12820(7) 0.79004(15) 0.0168(4) Uani 1 1 d . . . . .
H3 H 0.6920 0.1672 0.8286 0.020 Uiso 1 1 calc R . . . .
C4 C 0.4223(4) 0.12827(7) 0.66797(15) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.3219(4) 0.06881(7) 0.61181(16) 0.0177(4) Uani 1 1 d . . . . .
H5 H 0.1888 0.0678 0.5308 0.021 Uiso 1 1 calc R . . . .
C6 C 0.4167(4) 0.01158(7) 0.67441(16) 0.0201(4) Uani 1 1 d . . . . .
H6 H 0.3500 -0.0277 0.6364 0.024 Uiso 1 1 calc R . . . .
C7 C -0.2455(5) 0.2500 0.2904(2) 0.0143(4) Uani 1 2 d S T P . .
C8 C -0.3509(4) 0.19224(7) 0.22695(15) 0.0166(4) Uani 1 1 d . . . . .
H8 H -0.2845 0.1534 0.2669 0.020 Uiso 1 1 calc R . . . .
C9 C -0.5503(4) 0.19172(7) 0.10691(16) 0.0169(4) Uani 1 1 d . . . . .
H9 H -0.6198 0.1532 0.0660 0.020 Uiso 1 1 calc R . . . .
C10 C -0.6431(5) 0.2500 0.0497(2) 0.0150(5) Uani 1 2 d S T P . .
F1 F 0.7079(3) -0.04176(4) 0.85581(10) 0.0317(3) Uani 1 1 d . . . . .
F2 F -0.8411(3) 0.2500 -0.06821(12) 0.0219(3) Uani 1 2 d S T P . .
O1 O 0.0908(3) 0.19261(5) 0.48319(10) 0.0160(3) Uani 1 1 d . . . . .
O2 O 0.4324(4) 0.2500 0.65249(14) 0.0169(4) Uani 1 2 d S T P . .


_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
B1 C4 1.544(2) . ?
B1 O1 1.384(2) . ?
B1 O2 1.3812(18) . ?
B2 C7 1.545(3) . ?
B2 O1 1.3845(17) . ?
B2 O1 1.3845(17) 4_565 ?
C1 C2 1.378(2) . ?
C1 C6 1.374(2) . ?
C1 F1 1.3626(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(2) . ?
C4 C5 1.401(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.4057(18) 4_565 ?
C7 C8 1.4056(18) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.3776(18) . ?
C10 C9 1.3777(18) 4_565 ?
C10 F2 1.360(2) . ?
O2 B1 1.3812(18) 4_565 ?

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
O1 B1 C4 120.88(13) . . ?
O2 B1 C4 120.29(15) . . ?
O2 B1 O1 118.83(14) . . ?
O1 B2 C7 120.41(10) 4_565 . ?
O1 B2 C7 120.40(10) . . ?
O1 B2 O1 119.2(2) 4_565 . ?
C6 C1 C2 123.31(15) . . ?
F1 C1 C2 118.44(15) . . ?
F1 C1 C6 118.25(14) . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.67(15) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.61(14) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 B1 120.67(14) . . ?
C3 C4 C5 117.94(14) . . ?
C5 C4 B1 121.38(14) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.39(15) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.08(14) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C8 C7 B2 121.24(10) 4_565 . ?
C8 C7 B2 121.24(10) . . ?
C8 C7 C8 117.5(2) . 4_565 ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.71(14) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 117.91(15) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 C9 123.3(2) . 4_565 ?
F2 C10 C9 118.35(10) . 4_565 ?
F2 C10 C9 118.35(10) . . ?
B1 O1 B2 120.75(14) . . ?
B1 O2 B1 121.28(18) . 4_565 ?

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 C4 C5 C6 -179.11(14) . . . . ?
B2 C7 C8 C9 -177.77(16) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C3 C4 B1 178.55(13) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 B1 O1 B2 179.19(15) . . . . ?
C4 B1 O2 B1 -173.98(9) . . . 4_565 ?
C4 C5 C6 C1 0.3(2) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C7 B2 O1 B1 177.48(15) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C8 C7 C8 C9 0.0(3) 4_565 . . . ?
C8 C9 C10 C9 -0.8(3) . . . 4_565 ?
C8 C9 C10 F2 -179.66(14) . . . . ?
F1 C1 C2 C3 179.01(13) . . . . ?
F1 C1 C6 C5 -179.56(13) . . . . ?
O1 B1 C4 C3 -174.68(13) . . . . ?
O1 B1 C4 C5 4.3(2) . . . . ?
O1 B1 O2 B1 5.8(3) . . . 4_565 ?
O1 B2 C7 C8 2.1(3) 4_565 . . 4_565 ?
O1 B2 C7 C8 179.81(16) 4_565 . . . ?
O1 B2 C7 C8 -179.81(16) . . . 4_565 ?
O1 B2 C7 C8 -2.1(3) . . . . ?
O1 B2 O1 B1 -4.4(3) 4_565 . . . ?
O2 B1 C4 C3 5.1(2) . . . . ?
O2 B1 C4 C5 -175.96(14) . . . . ?
O2 B1 O1 B2 -0.6(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.494
_oxdiff_exptl_absorpt_empirical_full_min 0.580
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.878(3)
2 0.122(3)

####################################################################### 
# 
# 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_161107czf1_0m
_database_code_depnum_ccdc_archive 'CCDC 1547295'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H19 B O3'
_chemical_formula_weight         222.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0668(13)
_cell_length_b                   10.184(3)
_cell_length_c                   13.252(3)
_cell_angle_alpha                72.888(4)
_cell_angle_beta                 84.617(4)
_cell_angle_gamma                75.928(4)
_cell_volume                     633.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    57
_cell_measurement_theta_min      7.5
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4203
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         26.49
_reflns_number_total             2625
_reflns_number_gt                1738
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0689P)²+0.0465P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2625
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.9496(4) -0.3106(2) 0.87752(15) 0.0406(5) Uani 1 1 d . . .
C1 C 0.9345(3) -0.16986(17) 0.78953(12) 0.0405(4) Uani 1 1 d . . .
C2 C 0.7601(3) -0.12856(19) 0.70534(13) 0.0481(5) Uani 1 1 d . . .
H2A H 0.6489 -0.1875 0.7019 0.058 Uiso 1 1 calc R . .
C3 C 0.7454(4) -0.0036(2) 0.62673(14) 0.0523(5) Uani 1 1 d . . .
H3 H 0.6279 0.0198 0.5711 0.063 Uiso 1 1 calc R . .
C4 C 0.9049(3) 0.08652(18) 0.63069(13) 0.0454(4) Uani 1 1 d . . .
C5 C 1.0790(4) 0.04888(19) 0.71370(14) 0.0534(5) Uani 1 1 d . . .
H5 H 1.1867 0.1092 0.7177 0.064 Uiso 1 1 calc R . .
C6 C 1.0942(4) -0.07673(19) 0.79020(14) 0.0514(5) Uani 1 1 d . . .
H6 H 1.2157 -0.1007 0.8446 0.062 Uiso 1 1 calc R . .
C7 C 0.7169(4) 0.26546(19) 0.47549(13) 0.0536(5) Uani 1 1 d . . .
H7A H 0.5323 0.2765 0.5044 0.064 Uiso 1 1 calc R . .
H7B H 0.7429 0.2004 0.4328 0.064 Uiso 1 1 calc R . .
C8 C 0.7663(4) 0.40558(19) 0.40985(14) 0.0547(5) Uani 1 1 d . . .
H8A H 0.9494 0.3914 0.3797 0.066 Uiso 1 1 calc R . .
H8B H 0.7549 0.4660 0.4554 0.066 Uiso 1 1 calc R . .
C9 C 0.5677(4) 0.47932(19) 0.32182(14) 0.0537(5) Uani 1 1 d . . .
H9A H 0.3852 0.4967 0.3521 0.064 Uiso 1 1 calc R . .
H9B H 0.5743 0.4175 0.2777 0.064 Uiso 1 1 calc R . .
C10 C 0.6245(4) 0.6179(2) 0.25351(14) 0.0582(5) Uani 1 1 d . . .
H10A H 0.6168 0.6794 0.2979 0.070 Uiso 1 1 calc R . .
H10B H 0.8084 0.6001 0.2244 0.070 Uiso 1 1 calc R . .
C11 C 0.4340(5) 0.6935(2) 0.16474(16) 0.0723(6) Uani 1 1 d . . .
H11A H 0.2500 0.7115 0.1937 0.087 Uiso 1 1 calc R . .
H11B H 0.4419 0.6324 0.1200 0.087 Uiso 1 1 calc R . .
C12 C 0.4932(6) 0.8313(2) 0.09772(18) 0.0926(8) Uani 1 1 d . . .
H12A H 0.4763 0.8945 0.1404 0.139 Uiso 1 1 calc R . .
H12B H 0.3660 0.8723 0.0414 0.139 Uiso 1 1 calc R . .
H12C H 0.6749 0.8147 0.0686 0.139 Uiso 1 1 calc R . .
O1 O 1.1758(2) -0.37780(13) 0.93778(9) 0.0526(4) Uani 1 1 d . . .
H1 H 1.3059 -0.3450 0.9097 0.079 Uiso 1 1 calc R . .
O2 O 0.7339(2) -0.37242(13) 0.89942(10) 0.0534(4) Uani 1 1 d . . .
H2 H 0.7702 -0.4443 0.9487 0.080 Uiso 1 1 calc R . .
O3 O 0.9079(3) 0.21328(13) 0.55861(10) 0.0599(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
B1 O2 1.358(2) . ?
B1 O1 1.374(2) . ?
B1 C1 1.549(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.390(2) . ?
C2 C3 1.378(2) . ?
C3 C4 1.377(3) . ?
C4 O3 1.364(2) . ?
C4 C5 1.380(2) . ?
C5 C6 1.369(2) . ?
C7 O3 1.428(2) . ?
C7 C8 1.503(2) . ?
C8 C9 1.508(2) . ?
C9 C10 1.514(3) . ?
C10 C11 1.492(3) . ?
C11 C12 1.506(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
O2 B1 O1 116.76(15) . . ?
O2 B1 C1 120.61(14) . . ?
O1 B1 C1 122.63(15) . . ?
C2 C1 C6 115.86(16) . . ?
C2 C1 B1 122.16(15) . . ?
C6 C1 B1 121.98(15) . . ?
C3 C2 C1 122.53(16) . . ?
C4 C3 C2 119.90(16) . . ?
O3 C4 C3 125.61(16) . . ?
O3 C4 C5 115.45(15) . . ?
C3 C4 C5 118.94(17) . . ?
C6 C5 C4 120.37(17) . . ?
C5 C6 C1 122.39(16) . . ?
O3 C7 C8 106.96(15) . . ?
C7 C8 C9 113.52(16) . . ?
C8 C9 C10 113.31(17) . . ?
C11 C10 C9 114.94(17) . . ?
C10 C11 C12 114.23(19) . . ?
C4 O3 C7 118.84(14) . . ?

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
O2 B1 C1 C2 -25.1(3) . . . . ?
O1 B1 C1 C2 155.84(17) . . . . ?
O2 B1 C1 C6 154.65(17) . . . . ?
O1 B1 C1 C6 -24.4(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
B1 C1 C2 C3 -179.98(16) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 O3 -179.45(16) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
O3 C4 C5 C6 -179.48(16) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
B1 C1 C6 C5 -178.92(17) . . . . ?
O3 C7 C8 C9 -176.45(15) . . . . ?
C7 C8 C9 C10 -177.91(16) . . . . ?
C8 C9 C10 C11 179.39(17) . . . . ?
C9 C10 C11 C12 179.90(19) . . . . ?
C3 C4 O3 C7 5.3(3) . . . . ?
C5 C4 O3 C7 -174.60(15) . . . . ?
C8 C7 O3 C4 179.56(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_czf10
_database_code_depnum_ccdc_archive 'CCDC 1547298'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_audit_creation_date             2016-10-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H6 B I O2'
_chemical_formula_sum            'C6 H6 B I O2'
_chemical_formula_weight         247.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H B I'
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'
I I -0.3257 6.8362 '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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   19.5310(10)
_cell_length_b                   18.4544(8)
_cell_length_c                   9.7999(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3532.2(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1015
_cell_measurement_temperature    294.84(10)
_cell_measurement_theta_max      69.9460
_cell_measurement_theta_min      4.7750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    28.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0990
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9105
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         4.528
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.84(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3376
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00 -15.00   1.00    1.00    --  -41.56 125.00  60.00   48
  2  ω    -63.00  -2.00   1.00    1.00    --  -41.56 125.00-180.00   61
  3  ω     23.00  60.00   1.00    1.00    --   41.56-125.00  30.00   37
  4  ω     95.00 173.00   1.00    2.00    --  105.88 125.00-180.00   78
  5  ω     51.00 127.00   1.00    2.00    --  105.88 -45.00  30.00   76
  6  ω     98.00 127.00   1.00    2.00    --  105.88 125.00-120.00   29
  7  ω    112.00 143.00   1.00    2.00    --  105.88 125.00   0.00   31
  8  ω    147.00 174.00   1.00    2.00    --  105.88 125.00-120.00   27
  9  ω     35.00  88.00   1.00    2.00    --  105.88-125.00 -60.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0090113000
_diffrn_orient_matrix_UB_12      0.0657743000
_diffrn_orient_matrix_UB_13      0.0950837000
_diffrn_orient_matrix_UB_21      -0.0710765000
_diffrn_orient_matrix_UB_22      -0.0282999000
_diffrn_orient_matrix_UB_23      0.0427041000
_diffrn_orient_matrix_UB_31      0.0330286000
_diffrn_orient_matrix_UB_32      -0.0429081000
_diffrn_orient_matrix_UB_33      0.1176353000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1833
_reflns_number_total             3145
_reflns_odcompleteness_completeness 99.86
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         13.807
_refine_diff_density_min         -9.100
_refine_diff_density_rms         0.575
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.551
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         3145
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.2134
_refine_ls_R_factor_gt           0.1632
_refine_ls_restrained_S_all      1.547
_refine_ls_shift/su_max          0.059
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4235
_refine_ls_wR_factor_ref         0.4661
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uiso(B1) = Uiso(B2)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9), C1(H1A), C3(H3), C10(H10), C12(H12)
4.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
I1 I 0.16989(10) 0.23186(10) 0.0244(2) 0.0326(7) Uiso 1 1 d . U . . .
I2 I 0.20545(13) 0.54108(14) 0.0308(3) 0.0510(8) Uiso 1 1 d . U . . .
C5 C 0.3445(13) 0.4205(15) 0.024(3) 0.021(5) Uiso 1 1 d . U . . .
B1 B 0.3906(13) 0.4934(15) 0.017(3) 0.014(4) Uiso 1 1 d . U . . .
C11 C 0.0565(13) 0.7545(13) 0.009(2) 0.017(5) Uiso 1 1 d . U . . .
O1 O 0.4142(9) 0.5184(9) -0.1044(16) 0.016(4) Uiso 1 1 d . U . . .
H1 H 0.4517 0.5375 -0.0932 0.024 Uiso 1 1 calc GR . . . .
O3 O -0.0124(9) 0.8501(9) -0.1188(18) 0.021(4) Uiso 1 1 d . U . . .
H3A H 0.0146 0.8810 -0.1454 0.031 Uiso 1 1 calc GR . . . .
O2 O 0.4129(11) 0.5250(11) 0.130(2) 0.034(5) Uiso 1 1 d . U . . .
H2 H 0.3957 0.5050 0.1967 0.051 Uiso 1 1 calc GR . . . .
C8 C 0.1420(16) 0.6353(16) 0.020(3) 0.029(6) Uiso 1 1 d . U . . .
O4 O -0.0092(10) 0.8603(11) 0.1175(19) 0.023(4) Uiso 1 1 d . U . . .
C4 C 0.3158(13) 0.3991(15) 0.142(3) 0.022(6) Uiso 1 1 d . U . . .
H4 H 0.3281 0.4220 0.2226 0.027 Uiso 1 1 calc R . . . .
C6 C 0.3182(11) 0.3908(12) -0.100(2) 0.011(5) Uiso 1 1 d . U . . .
H6 H 0.3328 0.4087 -0.1837 0.014 Uiso 1 1 calc R . . . .
B2 B 0.0106(14) 0.8213(14) 0.007(3) 0.014(4) Uiso 1 1 d . U . . .
C7 C 0.1188(14) 0.6559(15) -0.103(3) 0.026(6) Uiso 1 1 d . U . . .
H7 H 0.1304 0.6302 -0.1814 0.031 Uiso 1 1 calc R . . . .
C9 C 0.1222(17) 0.6674(18) 0.140(3) 0.038(7) Uiso 1 1 d . U . . .
H9 H 0.1358 0.6487 0.2234 0.046 Uiso 1 1 calc R . . . .
C1 C 0.2724(14) 0.3371(16) -0.095(3) 0.027(6) Uiso 1 1 d . U . . .
H1A H 0.2587 0.3162 -0.1765 0.032 Uiso 1 1 calc R . . . .
C3 C 0.2670(14) 0.3423(15) 0.145(3) 0.022(6) Uiso 1 1 d . U . . .
H3 H 0.2496 0.3254 0.2274 0.026 Uiso 1 1 calc R . . . .
C10 C 0.0820(14) 0.7271(15) 0.132(3) 0.026(6) Uiso 1 1 d . U . . .
H10 H 0.0708 0.7510 0.2122 0.031 Uiso 1 1 calc R . . . .
C2 C 0.2454(11) 0.3117(12) 0.019(2) 0.010(4) Uiso 1 1 d . U . . .
C12 C 0.0763(14) 0.7173(14) -0.111(3) 0.022(6) Uiso 1 1 d . U . . .
H12 H 0.0611 0.7336 -0.1953 0.026 Uiso 1 1 calc R . . . .
H4A H -0.028(12) 0.826(13) 0.13(2) 0.00(6) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C2 2.09(2) . ?
I2 C8 2.14(3) . ?
C5 B1 1.62(4) . ?
C5 C4 1.34(4) . ?
C5 C6 1.43(3) . ?
B1 O1 1.35(3) . ?
B1 O2 1.33(3) . ?
C11 B2 1.52(4) . ?
C11 C10 1.40(4) . ?
C11 C12 1.41(4) . ?
O1 H1 0.8200 . ?
O3 H3A 0.8200 . ?
O3 B2 1.41(3) . ?
O2 H2 0.8200 . ?
C8 C7 1.34(4) . ?
C8 C9 1.37(4) . ?
O4 B2 1.36(3) . ?
O4 H4A 0.7(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.42(4) . ?
C6 H6 0.9300 . ?
C6 C1 1.34(4) . ?
B2 H4A 1.4(2) . ?
C7 H7 0.9300 . ?
C7 C12 1.41(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.36(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.32(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.42(3) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 B1 121(2) . . ?
C4 C5 C6 118(2) . . ?
C6 C5 B1 119(2) . . ?
O1 B1 C5 121(2) . . ?
O2 B1 C5 121(2) . . ?
O2 B1 O1 118(2) . . ?
C10 C11 B2 121(2) . . ?
C10 C11 C12 116(2) . . ?
C12 C11 B2 123(2) . . ?
B1 O1 H1 109.5 . . ?
B2 O3 H3A 109.5 . . ?
B1 O2 H2 109.5 . . ?
C7 C8 I2 118(2) . . ?
C7 C8 C9 123(3) . . ?
C9 C8 I2 118(2) . . ?
B2 O4 H4A 78(10) . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C3 121(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C6 H6 120.2 . . ?
C1 C6 C5 120(2) . . ?
C1 C6 H6 120.2 . . ?
C11 B2 H4A 111(10) . . ?
O3 B2 C11 120(2) . . ?
O3 B2 H4A 123(9) . . ?
O4 B2 C11 126(2) . . ?
O4 B2 O3 114(2) . . ?
O4 B2 H4A 31(10) . . ?
C8 C7 H7 120.8 . . ?
C8 C7 C12 118(3) . . ?
C12 C7 H7 120.8 . . ?
C8 C9 H9 121.2 . . ?
C10 C9 C8 118(3) . . ?
C10 C9 H9 121.2 . . ?
C6 C1 H1A 117.8 . . ?
C2 C1 C6 124(3) . . ?
C2 C1 H1A 117.8 . . ?
C4 C3 H3 120.9 . . ?
C4 C3 C2 118(2) . . ?
C2 C3 H3 120.9 . . ?
C11 C10 H10 118.3 . . ?
C9 C10 C11 123(3) . . ?
C9 C10 H10 118.3 . . ?
C1 C2 I1 123.9(19) . . ?
C1 C2 C3 118(2) . . ?
C3 C2 I1 117.8(17) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 C11 121(2) . . ?
C7 C12 H12 119.7 . . ?

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
I2 C8 C7 C12 179(2) . . . . ?
I2 C8 C9 C10 180(2) . . . . ?
C5 C4 C3 C2 -4(4) . . . . ?
C5 C6 C1 C2 5(4) . . . . ?
B1 C5 C4 C3 170(2) . . . . ?
B1 C5 C6 C1 -171(2) . . . . ?
C8 C7 C12 C11 -3(4) . . . . ?
C8 C9 C10 C11 4(5) . . . . ?
C4 C5 B1 O1 -174(2) . . . . ?
C4 C5 B1 O2 14(4) . . . . ?
C4 C5 C6 C1 -8(4) . . . . ?
C4 C3 C2 I1 -176.8(19) . . . . ?
C4 C3 C2 C1 1(4) . . . . ?
C6 C5 B1 O1 -12(3) . . . . ?
C6 C5 B1 O2 176(2) . . . . ?
C6 C5 C4 C3 8(4) . . . . ?
C6 C1 C2 I1 176(2) . . . . ?
C6 C1 C2 C3 -1(4) . . . . ?
B2 C11 C10 C9 179(3) . . . . ?
B2 C11 C12 C7 -180(2) . . . . ?
C7 C8 C9 C10 -6(5) . . . . ?
C9 C8 C7 C12 6(5) . . . . ?
C10 C11 B2 O3 177(2) . . . . ?
C10 C11 B2 O4 1(4) . . . . ?
C10 C11 C12 C7 1(4) . . . . ?
C12 C11 B2 O3 -2(4) . . . . ?
C12 C11 B2 O4 -179(3) . . . . ?
C12 C11 C10 C9 -2(4) . . . . ?

_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 0.000 0.500 -0.876 289.0 72.2 ?
2 0.500 0.000 -0.843 289.0 72.2 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.132
_oxdiff_exptl_absorpt_empirical_full_min 0.820
####################################################################### 
# 
# 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_20161103a
_database_code_depnum_ccdc_archive 'CCDC 1547113'
_audit_update_record             
;
2017-05-01 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_audit_creation_date             2016-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H7 B O3'
_chemical_formula_sum            'C6 H7 B O3'
_chemical_formula_weight         137.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1B1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.3451(6)
_cell_length_b                   5.0353(2)
_cell_length_c                   17.3021(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.473(4)
_cell_angle_gamma                90
_cell_volume                     1249.73(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3728
_cell_measurement_temperature    99.8(4)
_cell_measurement_theta_max      28.9500
_cell_measurement_theta_min      4.0100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.822
_diffrn_reflns_theta_min         3.675
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  11.00   1.00    4.00    --   12.61 -57.00  60.00   70
  2  ω     21.00  51.00   1.00    4.00    --   12.61 -99.00   0.00   30
  3  ω    -20.00  48.00   1.00    4.00    --   12.61 -99.00 -30.00   68
  4  ω     29.00  80.00   1.00    4.00    --   12.61  57.00-150.00   51
  5  ω    -16.00  85.00   1.00    4.00    --   12.61  77.00 120.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0242502000
_diffrn_orient_matrix_UB_12      0.1222741000
_diffrn_orient_matrix_UB_13      0.0029226000
_diffrn_orient_matrix_UB_21      0.0118087000
_diffrn_orient_matrix_UB_22      0.0305832000
_diffrn_orient_matrix_UB_23      -0.0387411000
_diffrn_orient_matrix_UB_31      -0.0414107000
_diffrn_orient_matrix_UB_32      -0.0628383000
_diffrn_orient_matrix_UB_33      -0.0131833000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2587
_reflns_number_total             3148
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_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         0.383
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.073
_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)+(0.0507P)²+0.9246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1295
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3A), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5A), O6(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.07300(8) 0.5226(2) 0.08547(7) 0.0175(3) Uani 1 1 d . . . . .
H1 H -0.1010 0.3808 0.0877 0.026 Uiso 1 1 calc GR . . . .
O2 O 0.30849(9) 0.2410(2) 0.28146(7) 0.0191(3) Uani 1 1 d . . . . .
H2 H 0.3598 0.2670 0.3013 0.029 Uiso 1 1 calc GR . . . .
O3 O 0.32752(8) 0.6974(2) 0.26248(7) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.2948 0.8296 0.2568 0.029 Uiso 1 1 calc GR . . . .
C1 C 0.01065(11) 0.5017(3) 0.12534(9) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.02618(11) 0.3009(3) 0.17904(9) 0.0138(3) Uani 1 1 d . . . . .
H2A H -0.0195 0.1741 0.1884 0.017 Uiso 1 1 calc R . . . .
C3 C 0.11064(11) 0.2919(3) 0.21848(9) 0.0132(3) Uani 1 1 d . . . . .
H3A H 0.1216 0.1548 0.2534 0.016 Uiso 1 1 calc R . . . .
C4 C 0.17981(11) 0.4835(3) 0.20718(9) 0.0123(3) Uani 1 1 d . . . . .
C5 C 0.16131(11) 0.6831(3) 0.15272(9) 0.0140(3) Uani 1 1 d . . . . .
H5 H 0.2061 0.8131 0.1441 0.017 Uiso 1 1 calc R . . . .
C6 C 0.07827(11) 0.6924(3) 0.11126(9) 0.0143(3) Uani 1 1 d . . . . .
H6 H 0.0680 0.8244 0.0746 0.017 Uiso 1 1 calc R . . . .
B1 B 0.27442(12) 0.4743(3) 0.25248(10) 0.0127(3) Uani 1 1 d . . . . .
O4 O 0.83857(8) 0.4754(2) 0.58487(7) 0.0181(3) Uani 1 1 d . . . . .
H4 H 0.8651 0.6195 0.5841 0.027 Uiso 1 1 calc GR . . . .
O5 O 0.47428(9) 0.2393(2) 0.36215(8) 0.0230(3) Uani 1 1 d . . . . .
H5A H 0.5083 0.1102 0.3686 0.034 Uiso 1 1 calc GR . . . .
O6 O 0.49434(8) 0.6953(2) 0.34262(7) 0.0215(3) Uani 1 1 d . . . . .
H6A H 0.4435 0.6709 0.3217 0.032 Uiso 1 1 calc GR . . . .
C7 C 0.76298(11) 0.4809(3) 0.53471(9) 0.0138(3) Uani 1 1 d . . . . .
C8 C 0.75271(11) 0.6776(3) 0.47917(9) 0.0138(3) Uani 1 1 d . . . . .
H8 H 0.7971 0.8111 0.4745 0.017 Uiso 1 1 calc R . . . .
C9 C 0.67515(11) 0.6722(3) 0.43055(9) 0.0130(3) Uani 1 1 d . . . . .
H9 H 0.6673 0.8072 0.3944 0.016 Uiso 1 1 calc R . . . .
C10 C 0.60856(10) 0.4701(3) 0.43438(9) 0.0127(3) Uani 1 1 d . . . . .
C11 C 0.62225(11) 0.2732(3) 0.49043(9) 0.0139(3) Uani 1 1 d . . . . .
H11 H 0.5795 0.1350 0.4939 0.017 Uiso 1 1 calc R . . . .
C12 C 0.69804(11) 0.2782(3) 0.54106(9) 0.0146(3) Uani 1 1 d . . . . .
H12 H 0.7051 0.1475 0.5786 0.018 Uiso 1 1 calc R . . . .
B2 B 0.52295(12) 0.4664(4) 0.37805(10) 0.0137(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C1 1.3831(18) . ?
O2 H2 0.8200 . ?
O2 B1 1.366(2) . ?
O3 H3 0.8200 . ?
O3 B1 1.368(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.388(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.386(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.399(2) . ?
C4 C5 1.401(2) . ?
C4 B1 1.562(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(2) . ?
C6 H6 0.9300 . ?
O4 H4 0.8200 . ?
O4 C7 1.3836(18) . ?
O5 H5A 0.8200 . ?
O5 B2 1.366(2) . ?
O6 H6A 0.8200 . ?
O6 B2 1.367(2) . ?
C7 C8 1.387(2) . ?
C7 C12 1.387(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(2) . ?
C10 C11 1.400(2) . ?
C10 B2 1.562(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
B1 O2 H2 109.5 . . ?
B1 O3 H3 109.5 . . ?
O1 C1 C2 121.49(14) . . ?
O1 C1 C6 117.68(13) . . ?
C6 C1 C2 120.81(14) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 C1 119.16(14) . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 H3A 119.1 . . ?
C2 C3 C4 121.79(14) . . ?
C4 C3 H3A 119.1 . . ?
C3 C4 C5 117.25(14) . . ?
C3 C4 B1 121.57(13) . . ?
C5 C4 B1 121.17(14) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 121.96(14) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 118.99(14) . . ?
C5 C6 H6 120.5 . . ?
O2 B1 O3 117.56(14) . . ?
O2 B1 C4 121.10(14) . . ?
O3 B1 C4 121.31(14) . . ?
C7 O4 H4 109.5 . . ?
B2 O5 H5A 109.5 . . ?
B2 O6 H6A 109.5 . . ?
O4 C7 C8 121.83(14) . . ?
O4 C7 C12 117.30(14) . . ?
C8 C7 C12 120.86(14) . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.05(14) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 121.96(14) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 C11 117.18(14) . . ?
C9 C10 B2 120.88(14) . . ?
C11 C10 B2 121.94(14) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.87(14) . . ?
C12 C11 H11 119.1 . . ?
C7 C12 C11 119.04(14) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
O5 B2 O6 117.67(14) . . ?
O5 B2 C10 122.24(14) . . ?
O6 B2 C10 120.09(14) . . ?

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
O1 C1 C2 C3 -178.78(13) . . . . ?
O1 C1 C6 C5 177.32(13) . . . . ?
C1 C2 C3 C4 1.7(2) . . . . ?
C2 C1 C6 C5 -1.2(2) . . . . ?
C2 C3 C4 C5 -1.5(2) . . . . ?
C2 C3 C4 B1 179.30(14) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C3 C4 B1 O2 24.7(2) . . . . ?
C3 C4 B1 O3 -157.36(15) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C5 C4 B1 O2 -154.50(15) . . . . ?
C5 C4 B1 O3 23.4(2) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
B1 C4 C5 C6 179.13(14) . . . . ?
O4 C7 C8 C9 -179.95(14) . . . . ?
O4 C7 C12 C11 -178.45(14) . . . . ?
C7 C8 C9 C10 -2.0(2) . . . . ?
C8 C7 C12 C11 0.4(2) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
C8 C9 C10 B2 -178.92(14) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C9 C10 B2 O5 158.23(15) . . . . ?
C9 C10 B2 O6 -21.7(2) . . . . ?
C10 C11 C12 C7 -1.4(2) . . . . ?
C11 C10 B2 O5 -21.7(2) . . . . ?
C11 C10 B2 O6 158.41(15) . . . . ?
C12 C7 C8 C9 1.3(2) . . . . ?
B2 C10 C11 C12 -179.35(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.610
_oxdiff_exptl_absorpt_empirical_full_min 0.585
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
