#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:13:45 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180294 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150868.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150868
loop_
_publ_author_name
'Filthaus, Matthias'
'Oppel, Iris M.'
'Bettinger, Holger F.'
_publ_section_title
;
 Supramolecular structures and spontaneous resolution: the case of
 ortho-substituted phenylboronic acids
;
_journal_issue                   7
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1201
_journal_page_last               1207
_journal_paper_doi               10.1039/b719282g
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C12 H11 B O2'
_chemical_formula_weight         198.02
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.514(9)
_cell_angle_beta                 104.995(10)
_cell_angle_gamma                99.904(9)
_cell_formula_units_Z            4
_cell_length_a                   8.2637(9)
_cell_length_b                   9.2893(8)
_cell_length_c                   14.5479(19)
_cell_measurement_reflns_used    1613
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.94
_cell_volume                     1040.7(2)
_computing_cell_refinement       'CrysAlis RED 1.171.29, Oxford Diffraction'
_computing_data_collection       'CrysAlis CCD 1.171.29, Oxford Diffraction'
_computing_data_reduction        'CrysAlis RED 1.171.29, Oxford Diffraction'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      108(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Sapphire2-CCD, Oxford Diffraction'
_diffrn_measurement_method       '409 images at 1.0 deg in ω and 25 sec'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_sigmaI/netI    0.1022
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5955
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.579
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.863
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0878P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1590
_reflns_number_gt                1895
_reflns_number_total             3523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b719282g.txt
_cod_data_source_block           bettinger3
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150868
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.2654(5) 0.4161(4) 0.3940(2) 0.0282(8) Uani 1 1 d . . .
O11 O 0.2855(3) 0.5528(2) 0.45028(16) 0.0330(6) Uani 1 1 d D . .
H11 H 0.382(2) 0.581(4) 0.489(2) 0.081(16) Uiso 1 1 d D . .
O12 O 0.4073(3) 0.3546(2) 0.40521(15) 0.0295(5) Uani 1 1 d D . .
H12 H 0.384(5) 0.2677(17) 0.375(2) 0.056(12) Uiso 1 1 d D . .
C11 C 0.0492(4) 0.2645(3) 0.2286(2) 0.0318(8) Uani 1 1 d . . .
C12 C 0.0838(4) 0.3336(3) 0.3266(2) 0.0300(7) Uani 1 1 d . . .
C13 C -0.0510(4) 0.3198(3) 0.3698(3) 0.0380(8) Uani 1 1 d . . .
H13 H -0.0294 0.3662 0.4358 0.046 Uiso 1 1 calc R . .
C14 C -0.2151(4) 0.2392(4) 0.3170(3) 0.0494(10) Uani 1 1 d . . .
H14 H -0.3053 0.2307 0.3466 0.059 Uiso 1 1 calc R . .
C15 C -0.2455(5) 0.1723(4) 0.2219(3) 0.0542(11) Uani 1 1 d . . .
H15 H -0.3574 0.1168 0.1857 0.065 Uiso 1 1 calc R . .
C16 C -0.1163(5) 0.1843(4) 0.1784(3) 0.0472(9) Uani 1 1 d . . .
H16 H -0.1405 0.1366 0.1124 0.057 Uiso 1 1 calc R . .
C11' C 0.1805(4) 0.2829(3) 0.1770(2) 0.0311(7) Uani 1 1 d . . .
C12' C 0.2030(4) 0.1618(4) 0.1151(2) 0.0435(9) Uani 1 1 d . . .
H12' H 0.1360 0.0649 0.1086 0.052 Uiso 1 1 calc R . .
C13' C 0.3212(5) 0.1814(4) 0.0634(3) 0.0516(10) Uani 1 1 d . . .
H13' H 0.3352 0.0981 0.0221 0.062 Uiso 1 1 calc R . .
C14' C 0.4184(5) 0.3210(4) 0.0716(3) 0.0512(10) Uani 1 1 d . . .
H14' H 0.4980 0.3344 0.0351 0.061 Uiso 1 1 calc R . .
C15' C 0.4003(4) 0.4417(4) 0.1328(2) 0.0394(8) Uani 1 1 d . . .
H15' H 0.4690 0.5379 0.1392 0.047 Uiso 1 1 calc R . .
C16' C 0.2828(4) 0.4232(3) 0.1846(2) 0.0324(7) Uani 1 1 d . . .
H16' H 0.2711 0.5072 0.2263 0.039 Uiso 1 1 calc R . .
B2 B 0.3324(4) 0.9181(3) 0.3621(3) 0.0240(8) Uani 1 1 d . . .
O21 O 0.3323(3) 0.8513(2) 0.43910(14) 0.0282(5) Uani 1 1 d D . .
H21 H 0.293(5) 0.7606(13) 0.427(3) 0.062(12) Uiso 1 1 d D . .
O22 O 0.4320(3) 1.0593(2) 0.38064(15) 0.0285(5) Uani 1 1 d D . .
H22 H 0.498(3) 1.082(3) 0.4363(11) 0.037(10) Uiso 1 1 d D . .
C21 C 0.0621(4) 0.7662(3) 0.2188(2) 0.0274(7) Uani 1 1 d . . .
C22 C 0.2359(4) 0.8430(3) 0.2535(2) 0.0267(7) Uani 1 1 d . . .
C23 C 0.3341(4) 0.8458(3) 0.1883(2) 0.0314(7) Uani 1 1 d . . .
H23 H 0.4505 0.8991 0.2108 0.038 Uiso 1 1 calc R . .
C24 C 0.2667(5) 0.7736(3) 0.0924(2) 0.0372(8) Uani 1 1 d . . .
H24 H 0.3361 0.7761 0.0495 0.045 Uiso 1 1 calc R . .
C25 C 0.0976(5) 0.6980(3) 0.0596(2) 0.0380(8) Uani 1 1 d . . .
H25 H 0.0496 0.6482 -0.0065 0.046 Uiso 1 1 calc R . .
C26 C -0.0036(4) 0.6939(3) 0.1224(2) 0.0338(8) Uani 1 1 d . . .
H26 H -0.1199 0.6406 0.0987 0.041 Uiso 1 1 calc R . .
C21' C -0.0516(3) 0.7657(3) 0.2826(2) 0.0253(7) Uani 1 1 d . . .
C22' C -0.0579(4) 0.8991(3) 0.3390(2) 0.0309(7) Uani 1 1 d . . .
H22' H 0.0130 0.9904 0.3377 0.037 Uiso 1 1 calc R . .
C23' C -0.1679(4) 0.8983(4) 0.3970(2) 0.0342(8) Uani 1 1 d . . .
H23' H -0.1717 0.9891 0.4354 0.041 Uiso 1 1 calc R . .
C24' C -0.2713(4) 0.7664(4) 0.3989(2) 0.0420(9) Uani 1 1 d . . .
H24' H -0.3463 0.7664 0.4386 0.050 Uiso 1 1 calc R . .
C25' C -0.2664(4) 0.6344(4) 0.3436(2) 0.0409(9) Uani 1 1 d . . .
H25' H -0.3372 0.5434 0.3456 0.049 Uiso 1 1 calc R . .
C26' C -0.1579(4) 0.6346(3) 0.2851(2) 0.0354(8) Uani 1 1 d . . .
H26' H -0.1565 0.5435 0.2461 0.042 Uiso 1 1 calc R . .
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'
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
O11 B1 O12 117.1(3) . . ?
O11 B1 C12 119.3(3) . . ?
O12 B1 C12 123.5(3) . . ?
C16 C11 C12 118.7(3) . . ?
C16 C11 C11' 119.5(3) . . ?
C12 C11 C11' 121.7(3) . . ?
C11 C12 C13 118.8(3) . . ?
C11 C12 B1 124.3(3) . . ?
C13 C12 B1 116.8(3) . . ?
C14 C13 C12 120.9(3) . . ?
C15 C14 C13 119.4(3) . . ?
C14 C15 C16 120.8(4) . . ?
C15 C16 C11 121.5(4) . . ?
C16' C11' C12' 117.4(3) . . ?
C16' C11' C11 121.1(3) . . ?
C12' C11' C11 121.4(3) . . ?
C13' C12' C11' 121.0(3) . . ?
C14' C13' C12' 120.1(3) . . ?
C13' C14' C15' 120.0(3) . . ?
C16' C15' C14' 120.2(3) . . ?
C15' C16' C11' 121.2(3) . . ?
O21 B2 O22 117.3(3) . . ?
O21 B2 C22 125.0(3) . . ?
O22 B2 C22 117.6(3) . . ?
C26 C21 C22 118.9(3) . . ?
C26 C21 C21' 119.8(3) . . ?
C22 C21 C21' 121.3(3) . . ?
C23 C22 C21 118.5(3) . . ?
C23 C22 B2 116.6(3) . . ?
C21 C22 B2 124.8(3) . . ?
C24 C23 C22 121.9(3) . . ?
C25 C24 C23 119.0(3) . . ?
C24 C25 C26 120.4(3) . . ?
C21 C26 C25 121.2(3) . . ?
C26' C21' C22' 118.7(3) . . ?
C26' C21' C21 120.9(3) . . ?
C22' C21' C21 120.4(3) . . ?
C23' C22' C21' 120.1(3) . . ?
C24' C23' C22' 120.1(3) . . ?
C25' C24' C23' 120.3(3) . . ?
C24' C25' C26' 119.8(3) . . ?
C21' C26' C25' 120.9(3) . . ?
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 O11 1.364(4) . ?
B1 O12 1.374(4) . ?
B1 C12 1.556(5) . ?
C11 C16 1.389(4) . ?
C11 C12 1.408(4) . ?
C11 C11' 1.472(4) . ?
C12 C13 1.410(4) . ?
C13 C14 1.389(5) . ?
C14 C15 1.369(5) . ?
C15 C16 1.373(5) . ?
C11' C16' 1.397(4) . ?
C11' C12' 1.403(4) . ?
C12' C13' 1.383(5) . ?
C13' C14' 1.374(5) . ?
C14' C15' 1.380(4) . ?
C15' C16' 1.379(4) . ?
B2 O21 1.359(4) . ?
B2 O22 1.371(4) . ?
B2 C22 1.564(4) . ?
C21 C26 1.383(4) . ?
C21 C22 1.412(4) . ?
C21 C21' 1.483(4) . ?
C22 C23 1.398(4) . ?
C23 C24 1.378(4) . ?
C24 C25 1.376(5) . ?
C25 C26 1.389(4) . ?
C21' C26' 1.385(4) . ?
C21' C22' 1.398(4) . ?
C22' C23' 1.391(4) . ?
C23' C24' 1.377(4) . ?
C24' C25' 1.376(4) . ?
C25' C26' 1.388(4) . ?
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
C16 C11 C12 C13 -0.6(4) . . . . ?
C11' C11 C12 C13 175.7(3) . . . . ?
C16 C11 C12 B1 175.0(3) . . . . ?
C11' C11 C12 B1 -8.8(4) . . . . ?
O11 B1 C12 C11 133.5(3) . . . . ?
O12 B1 C12 C11 -50.9(4) . . . . ?
O11 B1 C12 C13 -50.9(4) . . . . ?
O12 B1 C12 C13 124.6(3) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
B1 C12 C13 C14 -175.6(3) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C11 -0.1(5) . . . . ?
C12 C11 C16 C15 0.5(5) . . . . ?
C11' C11 C16 C15 -175.8(3) . . . . ?
C16 C11 C11' C16' 130.9(3) . . . . ?
C12 C11 C11' C16' -45.3(4) . . . . ?
C16 C11 C11' C12' -46.4(4) . . . . ?
C12 C11 C11' C12' 137.4(3) . . . . ?
C16' C11' C12' C13' -0.4(5) . . . . ?
C11 C11' C12' C13' 177.0(3) . . . . ?
C11' C12' C13' C14' -0.3(5) . . . . ?
C12' C13' C14' C15' 1.1(5) . . . . ?
C13' C14' C15' C16' -1.1(5) . . . . ?
C14' C15' C16' C11' 0.3(5) . . . . ?
C12' C11' C16' C15' 0.4(4) . . . . ?
C11 C11' C16' C15' -177.0(3) . . . . ?
C26 C21 C22 C23 1.5(4) . . . . ?
C21' C21 C22 C23 -176.6(3) . . . . ?
C26 C21 C22 B2 -174.5(3) . . . . ?
C21' C21 C22 B2 7.4(4) . . . . ?
O21 B2 C22 C23 -126.7(3) . . . . ?
O22 B2 C22 C23 49.6(3) . . . . ?
O21 B2 C22 C21 49.4(4) . . . . ?
O22 B2 C22 C21 -134.3(3) . . . . ?
C21 C22 C23 C24 -1.3(4) . . . . ?
B2 C22 C23 C24 175.0(3) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C23 C24 C25 C26 -0.3(4) . . . . ?
C22 C21 C26 C25 -1.1(4) . . . . ?
C21' C21 C26 C25 177.1(3) . . . . ?
C24 C25 C26 C21 0.5(4) . . . . ?
C26 C21 C21' C26' 48.0(4) . . . . ?
C22 C21 C21' C26' -133.9(3) . . . . ?
C26 C21 C21' C22' -129.6(3) . . . . ?
C22 C21 C21' C22' 48.5(4) . . . . ?
C26' C21' C22' C23' 0.8(4) . . . . ?
C21 C21' C22' C23' 178.5(3) . . . . ?
C21' C22' C23' C24' -0.2(4) . . . . ?
C22' C23' C24' C25' 0.1(5) . . . . ?
C23' C24' C25' C26' -0.6(5) . . . . ?
C22' C21' C26' C25' -1.3(4) . . . . ?
C21 C21' C26' C25' -178.9(3) . . . . ?
C24' C25' C26' C21' 1.2(5) . . . . ?
