#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222486.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222486
loop_
_publ_author_name
'Dabrowski, Marek'
'Luliński, Sergiusz'
'Serwatowski, Janusz'
'Wilmowicz, Agnieszka'
_publ_section_title
;
 2,4-Dibutoxyphenylboronic acid
;
_journal_coeditor_code           TK2482
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1669
_journal_paper_doi               10.1107/S1600536809023332
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H23 B O4'
_chemical_formula_moiety         'C14 H23 B O4'
_chemical_formula_sum            'C14 H23 B O4'
_chemical_formula_weight         266.13
_chemical_melting_point          369
_chemical_name_common            '2,4-Dibutoxyphenylboronic acid'
_chemical_name_systematic
;
2,4-Dibutoxyphenylboronic acid
;
_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                112.747(11)
_cell_angle_beta                 94.311(11)
_cell_angle_gamma                100.385(11)
_cell_formula_units_Z            2
_cell_length_a                   5.3129(8)
_cell_length_b                   11.3611(13)
_cell_length_c                   13.7362(17)
_cell_measurement_temperature    100(2)
_cell_volume                     742.46(19)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2005)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2005)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2005)
;
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.6479
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Oxford Diffraction KM-4-CCD'
_diffrn_measurement_method       ω
_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  0.018
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14053
_diffrn_reflns_theta_full        28.0
_diffrn_reflns_theta_max         28.6
_diffrn_reflns_theta_min         3.1
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.092
_refine_ls_wR_factor_ref         0.095
_reflns_number_gt                2633
_reflns_number_total             3570
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2482.cif
_cod_data_source_block           I
_cod_original_cell_volume        742.45(17)
_cod_database_code               2222486
_cod_database_fobs_code          2222486
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.56253(19) 0.61272(9) 0.78929(7) 0.0153(2) Uani d . 1 . .
C C2 0.72694(19) 0.56726(10) 0.84327(8) 0.0170(2) Uani d . 1 . .
H H2 0.8262 0.5095 0.8031 0.020 Uiso calc R 1 . .
C C3 0.75323(19) 0.60219(10) 0.95310(8) 0.0171(2) Uani d . 1 . .
H H3 0.8666 0.5685 0.9869 0.021 Uiso calc R 1 . .
C C4 0.60985(19) 0.68740(10) 1.01210(7) 0.0155(2) Uani d . 1 . .
C C5 0.44559(18) 0.73795(9) 0.96259(8) 0.0159(2) Uani d . 1 . .
H H5 0.3502 0.7974 1.0036 0.019 Uiso calc R 1 . .
C C6 0.42293(18) 0.70058(9) 0.85288(8) 0.0146(2) Uani d . 1 . .
C C7 0.14424(19) 0.84955(10) 0.85803(8) 0.0167(2) Uani d . 1 . .
H H7A 0.2754 0.9274 0.9086 0.020 Uiso calc R 1 . .
H H7B 0.0232 0.8190 0.8992 0.020 Uiso calc R 1 . .
C C8 -0.00127(19) 0.88312(10) 0.77716(8) 0.0169(2) Uani d . 1 . .
H H8A -0.1220 0.8025 0.7244 0.020 Uiso calc R 1 . .
H H8B 0.1239 0.9154 0.7382 0.020 Uiso calc R 1 . .
C C9 -0.15422(19) 0.98636(10) 0.82756(8) 0.0187(2) Uani d . 1 . .
H H9A -0.0328 1.0699 0.8751 0.022 Uiso calc R 1 . .
H H9B -0.2692 0.9580 0.8717 0.022 Uiso calc R 1 . .
C C10 -0.3170(2) 1.00821(11) 0.74256(9) 0.0240(2) Uani d . 1 . .
H H10A -0.4393 0.9259 0.6962 0.036 Uiso calc R 1 . .
H H10B -0.2032 1.0378 0.6996 0.036 Uiso calc R 1 . .
H H10C -0.4132 1.0750 0.7772 0.036 Uiso calc R 1 . .
C C7' 0.79357(19) 0.68855(10) 1.17808(8) 0.0173(2) Uani d . 1 . .
H H7A' 0.9734 0.7183 1.1687 0.021 Uiso calc R 1 . .
H H7B' 0.7528 0.5918 1.1514 0.021 Uiso calc R 1 . .
C C8' 0.7655(2) 0.74945(10) 1.29481(8) 0.0192(2) Uani d . 1 . .
H H8A' 0.5885 0.7140 1.3037 0.023 Uiso calc R 1 . .
H H8B' 0.7892 0.8454 1.3185 0.023 Uiso calc R 1 . .
C C9' 0.9634(2) 0.72152(11) 1.36433(8) 0.0244(3) Uani d . 1 . .
H H9A' 1.1400 0.7584 1.3560 0.029 Uiso calc R 1 . .
H H9B' 0.9421 0.6255 1.3391 0.029 Uiso calc R 1 . .
C C10' 0.9371(3) 0.77900(13) 1.48245(9) 0.0378(3) Uani d . 1 . .
H H10D 0.7640 0.7414 1.4915 0.057 Uiso calc R 1 . .
H H10E 0.9621 0.8743 1.5085 0.057 Uiso calc R 1 . .
H H10F 1.0684 0.7582 1.5233 0.057 Uiso calc R 1 . .
O O1 0.73656(14) 0.51449(8) 0.61804(6) 0.0245(2) Uani d . 1 . .
O O2 0.34414(15) 0.57844(8) 0.60251(6) 0.0253(2) Uani d . 1 . .
O O3 0.26778(13) 0.74719(7) 0.79858(5) 0.01810(17) Uani d . 1 . .
O O4 0.61551(13) 0.72922(7) 1.12026(5) 0.01908(18) Uani d . 1 . .
B B1 0.5445(2) 0.56749(11) 0.66526(9) 0.0170(2) Uani d . 1 . .
H H1o 0.709(3) 0.4847(14) 0.5482(13) 0.049(4) Uiso d . 1 . .
H H2o 0.231(3) 0.6103(14) 0.6371(12) 0.051(4) Uiso d . 1 . .
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 116.20(8) ?
C2 C1 B1 . . 119.80(8) ?
C6 C1 B1 . . 123.99(9) ?
C3 C2 C1 . . 123.36(9) ?
C3 C2 H2 . . 118.3 ?
C1 C2 H2 . . 118.3 ?
C4 C3 C2 . . 118.41(9) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
O4 C4 C3 . . 124.59(9) ?
O4 C4 C5 . . 114.68(8) ?
C3 C4 C5 . . 120.73(9) ?
C6 C5 C4 . . 119.37(9) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
O3 C6 C5 . . 122.81(8) ?
O3 C6 C1 . . 115.27(8) ?
C5 C6 C1 . . 121.91(8) ?
O3 C7 C8 . . 106.65(8) ?
O3 C7 H7A . . 110.4 ?
C8 C7 H7A . . 110.4 ?
O3 C7 H7B . . 110.4 ?
C8 C7 H7B . . 110.4 ?
H7A C7 H7B . . 108.6 ?
C7 C8 C9 . . 113.05(8) ?
C7 C8 H8A . . 109.0 ?
C9 C8 H8A . . 109.0 ?
C7 C8 H8B . . 109.0 ?
C9 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C8 C9 C10 . . 111.28(8) ?
C8 C9 H9A . . 109.4 ?
C10 C9 H9A . . 109.4 ?
C8 C9 H9B . . 109.4 ?
C10 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O4 C7' C8' . . 107.43(8) ?
O4 C7' H7A' . . 110.2 ?
C8' C7' H7A' . . 110.2 ?
O4 C7' H7B' . . 110.2 ?
C8' C7' H7B' . . 110.2 ?
H7A' C7' H7B' . . 108.5 ?
C7' C8' C9' . . 111.40(8) ?
C7' C8' H8A' . . 109.3 ?
C9' C8' H8A' . . 109.3 ?
C7' C8' H8B' . . 109.3 ?
C9' C8' H8B' . . 109.3 ?
H8A' C8' H8B' . . 108.0 ?
C8' C9' C10' . . 112.88(9) ?
C8' C9' H9A' . . 109.0 ?
C10' C9' H9A' . . 109.0 ?
C8' C9' H9B' . . 109.0 ?
C10' C9' H9B' . . 109.0 ?
H9A' C9' H9B' . . 107.8 ?
C9' C10' H10D . . 109.5 ?
C9' C10' H10E . . 109.5 ?
H10D C10' H10E . . 109.5 ?
C9' C10' H10F . . 109.5 ?
H10D C10' H10F . . 109.5 ?
H10E C10' H10F . . 109.5 ?
B1 O1 H1o . . 113.8(9) ?
B1 O2 H2o . . 113.1(10) ?
C6 O3 C7 . . 119.23(7) ?
C4 O4 C7' . . 117.93(7) ?
O1 B1 O2 . . 118.73(9) ?
O1 B1 C1 . . 118.07(9) ?
O2 B1 C1 . . 123.20(9) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.3932(13) ?
C1 C6 . 1.4140(13) ?
C1 B1 . 1.5674(14) ?
C2 C3 . 1.3923(13) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3879(14) ?
C3 H3 . 0.9500 ?
C4 O4 . 1.3697(11) ?
C4 C5 . 1.3955(13) ?
C5 C6 . 1.3875(13) ?
C5 H5 . 0.9500 ?
C6 O3 . 1.3736(11) ?
C7 O3 . 1.4392(11) ?
C7 C8 . 1.5105(13) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.5217(13) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.5241(14) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C7' O4 . 1.4379(11) ?
C7' C8' . 1.5123(14) ?
C7' H7A' . 0.9900 ?
C7' H7B' . 0.9900 ?
C8' C9' . 1.5237(14) ?
C8' H8A' . 0.9900 ?
C8' H8B' . 0.9900 ?
C9' C10' . 1.5251(15) ?
C9' H9A' . 0.9900 ?
C9' H9B' . 0.9900 ?
C10' H10D . 0.9800 ?
C10' H10E . 0.9800 ?
C10' H10F . 0.9800 ?
O1 B1 . 1.3577(13) ?
O1 H1o . 0.876(16) ?
O2 B1 . 1.3727(13) ?
O2 H2o . 0.839(15) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1o O2 2_666 0.876(16) 1.889(17) 2.7649(11) 178.9(14)
O2 H2o O3 . 0.839(15) 2.129(15) 2.7469(10) 130.3(13)
O2 H2o O1 1_455 0.839(15) 2.610(15) 3.2205(12) 130.7(12)
C10 H10C O4 2_577 0.98 2.60 3.5739(15) 173.25(7)
C9' H9B' O1 2_767 0.99 2.71 3.4314(17) 130.04(8)
C7 H7B Cg 2_466 0.99 2.74 3.6237(12) 149
C7' H7B' Cg 1_656 0.99 2.80 3.7109(12) 153
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.25(15) ?
B1 C1 C2 C3 . . . . -179.69(9) ?
C1 C2 C3 C4 . . . . -0.48(15) ?
C2 C3 C4 O4 . . . . 179.58(9) ?
C2 C3 C4 C5 . . . . -0.72(15) ?
O4 C4 C5 C6 . . . . -179.21(8) ?
C3 C4 C5 C6 . . . . 1.07(15) ?
C4 C5 C6 O3 . . . . -179.22(9) ?
C4 C5 C6 C1 . . . . -0.24(14) ?
C2 C1 C6 O3 . . . . 178.18(8) ?
B1 C1 C6 O3 . . . . -0.84(14) ?
C2 C1 C6 C5 . . . . -0.88(14) ?
B1 C1 C6 C5 . . . . -179.89(9) ?
O3 C7 C8 C9 . . . . 177.25(8) ?
C7 C8 C9 C10 . . . . -174.85(9) ?
O4 C7' C8' C9' . . . . -175.14(8) ?
C7' C8' C9' C10' . . . . -178.76(10) ?
C5 C6 O3 C7 . . . . 6.91(13) ?
C1 C6 O3 C7 . . . . -172.13(8) ?
C8 C7 O3 C6 . . . . 177.59(8) ?
C3 C4 O4 C7' . . . . 3.91(14) ?
C5 C4 O4 C7' . . . . -175.81(8) ?
C8' C7' O4 C4 . . . . 178.89(8) ?
C2 C1 B1 O1 . . . . -17.36(14) ?
C6 C1 B1 O1 . . . . 161.62(10) ?
C2 C1 B1 O2 . . . . 162.36(10) ?
C6 C1 B1 O2 . . . . -18.66(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17345366
