#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/53/2015316.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_2015316
loop_
_publ_author_name
'Lulinski, Sergiusz'
'Serwatowski, Janusz'
_publ_section_title
;
 2-(Methoxycarbonyl)phenylboronic acid
;
_journal_coeditor_code           JZ3006
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o301
_journal_page_last               o303
_journal_paper_doi               10.1107/S0108270106012297
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C8 H9 B O4'
_chemical_formula_moiety         'C8 H9 B O4'
_chemical_formula_sum            'C8 H9 B O4'
_chemical_formula_weight         179.96
_chemical_melting_point          .375E-305
_chemical_name_systematic
;
2-(Methoxycarbonyl)phenylboronic acid
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.007(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   8.2764(2)
_cell_length_b                   19.7124(6)
_cell_length_c                   8.7321(3)
_cell_measurement_reflns_used    18642
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.03
_cell_measurement_theta_min      2.57
_cell_volume                     1291.07(7)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2005)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2005)
;
_computing_data_reduction
;
CrysAlis RED
;
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  SHELXTL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.6479
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.960
_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  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0122
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23407
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.62
_diffrn_reflns_theta_min         2.77
_diffrn_standards_decay_%        2
_diffrn_standards_number         '1 frame'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.98
_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    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0325
_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)+(0.0537P)²+0.2342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                2797
_reflns_number_total             3268
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz3006.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2015316
_cod_database_fobs_code          2015316
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
B B1A 0.7560(2) 0.2500 0.10927(19) 0.0147(3) Uani d S 1
O O2A 0.84020(9) 0.19131(4) 0.10383(10) 0.01859(17) Uani d . 1
C C4A 0.58490(18) 0.2500 0.14853(18) 0.0135(3) Uani d S 1
C C5A 0.40914(18) 0.2500 0.02271(17) 0.0135(3) Uani d S 1
C C6A 0.26290(19) 0.2500 0.06308(18) 0.0155(3) Uani d S 1
C C7A 0.28900(19) 0.2500 0.23082(18) 0.0164(3) Uani d S 1
C C8A 0.46185(19) 0.2500 0.35780(18) 0.0154(3) Uani d S 1
C C9A 0.60694(19) 0.2500 0.31652(18) 0.0153(3) Uani d S 1
C C10A 0.38300(18) 0.2500 -0.15829(18) 0.0151(3) Uani d S 1
O O11A 0.50296(14) 0.2500 -0.20031(13) 0.0217(2) Uani d S 1
O O12A 0.21027(13) 0.2500 -0.26413(13) 0.0189(2) Uani d S 1
C C13A 0.1733(2) 0.2500 -0.44150(18) 0.0205(3) Uani d S 1
H H2A 0.778(2) 0.1552(9) 0.106(2) 0.040(4) Uiso d . 1
H H6A 0.146(2) 0.2500 -0.024(2) 0.018(4) Uiso d S 1
H H7A 0.186(3) 0.2500 0.257(2) 0.020(4) Uiso d S 1
H H8A 0.485(2) 0.2500 0.472(2) 0.017(4) Uiso d S 1
H H9A 0.727(3) 0.2500 0.410(2) 0.019(4) Uiso d S 1
H H13B 0.2218(17) 0.2909(7) -0.4699(16) 0.022(3) Uiso d . 1
H H13A 0.043(3) 0.2500 -0.502(2) 0.022(5) Uiso d S 1
B B1B 0.64335(15) 0.03990(6) 0.23390(14) 0.0160(2) Uani d . 1
O O2B 0.63920(11) 0.07786(4) 0.10208(10) 0.02110(18) Uani d . 1
O O3B 0.59072(10) -0.02644(4) 0.20533(9) 0.01729(17) Uani d . 1
C C4B 0.72656(13) 0.07235(5) 0.41676(12) 0.0148(2) Uani d . 1
C C5B 0.62241(13) 0.09238(5) 0.50140(12) 0.0144(2) Uani d . 1
C C6B 0.69903(14) 0.12175(5) 0.66217(13) 0.0168(2) Uani d . 1
C C7B 0.88173(14) 0.13109(5) 0.74235(13) 0.0195(2) Uani d . 1
C C8B 0.98774(14) 0.11072(6) 0.66255(14) 0.0205(2) Uani d . 1
C C9B 0.91089(14) 0.08231(5) 0.50166(14) 0.0183(2) Uani d . 1
C C10B 0.42559(13) 0.08558(5) 0.42013(13) 0.0151(2) Uani d . 1
O O11B 0.32945(10) 0.08921(4) 0.49407(9) 0.01926(17) Uani d . 1
O O12B 0.36270(9) 0.07474(4) 0.25489(9) 0.01917(17) Uani d . 1
C C13B 0.17208(15) 0.06358(7) 0.16598(15) 0.0253(2) Uani d . 1
H H2B 0.574(2) 0.0605(9) 0.002(2) 0.045(5) Uiso d . 1
H H3B 0.609(2) -0.0490(10) 0.295(2) 0.051(5) Uiso d . 1
H H6B 0.6238(16) 0.1378(6) 0.7136(16) 0.017(3) Uiso d . 1
H H7B 0.9340(18) 0.1523(7) 0.8526(18) 0.025(3) Uiso d . 1
H H8B 1.1197(19) 0.1161(7) 0.7198(18) 0.028(4) Uiso d . 1
H H9B 0.9892(19) 0.0696(7) 0.4494(18) 0.027(3) Uiso d . 1
H H13D 0.152(2) 0.0539(8) 0.050(2) 0.032(4) Uiso d . 1
H H13E 0.1379(19) 0.0251(8) 0.2171(18) 0.029(4) Uiso d . 1
H H13F 0.1087(19) 0.1045(8) 0.1705(19) 0.030(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'
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_site_symmetry_1
_geom_angle
_geom_angle_publ_flag
O2A B1A O2A 4_565 116.34(12) y
O2A B1A C4A 4_565 121.50(6) y
O2A B1A C4A . 121.50(6) no
B1A O2A H2A . 112.0(10) no
C9A C4A C5A . 116.93(12) no
C9A C4A B1A . 119.48(12) y
C5A C4A B1A . 123.59(12) y
C6A C5A C4A . 121.62(13) no
C6A C5A C10A . 120.73(12) y
C4A C5A C10A . 117.65(12) y
C7A C6A C5A . 120.12(13) no
C7A C6A H6A . 119.8(11) no
C5A C6A H6A . 120.1(11) no
C6A C7A C8A . 119.36(13) no
C6A C7A H7A . 119.0(11) no
C8A C7A H7A . 121.6(11) no
C7A C8A C9A . 120.18(13) no
C7A C8A H8A . 121.9(11) no
C9A C8A H8A . 118.0(11) no
C8A C9A C4A . 121.80(13) no
C8A C9A H9A . 117.5(11) no
C4A C9A H9A . 120.7(11) no
O11A C10A O12A . 124.97(14) y
O11A C10A C5A . 123.66(13) y
O12A C10A C5A . 111.37(12) y
C10A O12A C13A . 114.93(11) no
O12A C13A H13B . 110.3(8) no
O12A C13A H13A . 105.2(11) no
H13B C13A H13A . 109.9(9) no
O2B B1B O3B . 118.63(9) y
O2B B1B C4B . 118.41(9) y
O3B B1B C4B . 122.67(9) y
B1B O2B H2B . 114.3(11) no
B1B O3B H3B . 114.1(13) no
C9B C4B C5B . 117.04(9) no
C9B C4B B1B . 120.21(9) no
C5B C4B B1B . 122.76(9) y
C6B C5B C4B . 121.63(9) no
C6B C5B C10B . 117.27(9) y
C4B C5B C10B . 121.05(9) y
C7B C6B C5B . 119.85(10) no
C7B C6B H6B . 120.3(7) no
C5B C6B H6B . 119.8(7) no
C6B C7B C8B . 119.60(10) no
C6B C7B H7B . 119.6(8) no
C8B C7B H7B . 120.8(8) no
C7B C8B C9B . 120.41(10) no
C7B C8B H8B . 120.5(8) no
C9B C8B H8B . 119.1(8) no
C8B C9B C4B . 121.46(10) no
C8B C9B H9B . 117.9(9) no
C4B C9B H9B . 120.6(9) no
O11B C10B O12B . 122.72(9) y
O11B C10B C5B . 124.87(9) y
O12B C10B C5B . 112.42(8) y
C10B O12B C13B . 116.35(8) no
O12B C13B H13D . 104.9(9) no
O12B C13B H13E . 109.3(8) no
H13D C13B H13E . 111.4(13) no
O12B C13B H13F . 109.6(9) no
H13D C13B H13F . 110.3(13) no
H13E C13B H13F . 111.1(12) no
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
B1A O2A 4_565 1.3616(11) y
B1A O2A . 1.3616(11) no
B1A C4A . 1.592(2) y
O2A H2A . 0.883(17) no
C4A C9A . 1.3997(19) no
C4A C5A . 1.4042(19) no
C5A C6A . 1.3963(19) no
C5A C10A . 1.502(2) y
C6A C7A . 1.387(2) no
C6A H6A . 0.945(18) no
C7A C8A . 1.392(2) no
C7A H7A . 0.973(19) no
C8A C9A . 1.392(2) no
C8A H8A . 0.931(19) no
C9A H9A . 0.983(19) no
C10A O11A . 1.1951(17) y
C10A O12A . 1.3344(17) y
O12A C13A . 1.4462(17) no
C13A H13B . 0.978(13) no
C13A H13A . 0.976(19) no
B1B O2B . 1.3610(13) y
B1B O3B . 1.3677(14) y
B1B C4B . 1.5823(15) y
O2B H2B . 0.880(19) no
O3B H3B . 0.858(19) no
C4B C9B . 1.3998(14) no
C4B C5B . 1.4083(14) no
C5B C6B . 1.3984(14) no
C5B C10B . 1.4825(14) y
C6B C7B . 1.3840(15) no
C6B H6B . 0.962(12) no
C7B C8B . 1.3906(16) no
C7B H7B . 0.968(14) no
C8B C9B . 1.3915(15) no
C8B H8B . 0.996(14) no
C9B H9B . 0.970(14) no
C10B O11B . 1.2204(12) y
C10B O12B . 1.3280(12) y
O12B C13B . 1.4507(13) no
C13B H13D . 0.969(15) no
C13B H13E . 0.981(15) no
C13B H13F . 0.972(16) no
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
_geom_hbond_publ_flag
O2A H2A O2B . 0.883(17) 1.901(17) 2.7835(11) 177.8(16) y
O2B H2B O3B 3_655 0.880(19) 1.870(19) 2.7451(11) 172.8(16) y
O3B H3B O11B 3_656 0.858(19) 1.87(2) 2.7187(11) 172.6(18) y
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
_geom_torsion_publ_flag
O2A B1A C4A C9A 4_565 -85.18(12) no
O2A B1A C4A C9A . 85.18(12) y
O2A B1A C4A C5A 4_565 94.82(12) y
O2A B1A C4A C5A . -94.82(12) no
C9A C4A C5A C6A . 0.0 no
B1A C4A C5A C6A . 180.0 no
C9A C4A C5A C10A . 180.0 no
B1A C4A C5A C10A . 0.0 no
C4A C5A C6A C7A . 0.0 no
C10A C5A C6A C7A . 180.0 no
C5A C6A C7A C8A . 0.0 no
C6A C7A C8A C9A . 0.0 no
C7A C8A C9A C4A . 0.0 no
C5A C4A C9A C8A . 0.0 no
B1A C4A C9A C8A . 180.0 no
C6A C5A C10A O11A . 180.0 no
C4A C5A C10A O11A . 0.0 no
C6A C5A C10A O12A . 0.0 no
C4A C5A C10A O12A . 180.0 no
O11A C10A O12A C13A . 0.0 no
C5A C10A O12A C13A . 180.0 no
O2B B1B C4B C9B . -71.88(13) no
O3B B1B C4B C9B . 101.97(12) no
O2B B1B C4B C5B . 108.12(11) no
O3B B1B C4B C5B . -78.04(13) no
C9B C4B C5B C6B . 0.83(14) no
B1B C4B C5B C6B . -179.17(9) no
C9B C4B C5B C10B . 178.36(9) no
B1B C4B C5B C10B . -1.63(15) y
C4B C5B C6B C7B . -0.63(15) no
C10B C5B C6B C7B . -178.26(9) no
C5B C6B C7B C8B . -0.43(16) no
C6B C7B C8B C9B . 1.27(16) no
C7B C8B C9B C4B . -1.07(16) no
C5B C4B C9B C8B . 0.02(15) no
B1B C4B C9B C8B . -179.98(10) no
C6B C5B C10B O11B . -17.14(15) y
C4B C5B C10B O11B . 165.22(10) y
C6B C5B C10B O12B . 163.00(9) y
C4B C5B C10B O12B . -14.64(13) no
O11B C10B O12B C13B . -3.24(14) y
C5B C10B O12B C13B . 176.62(9) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139059794
