#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:42 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180363 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/32/7203218.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_7203218
loop_
_publ_author_name
'Kenneth E. Maly'
'Thierry Maris'
'James D. Wuest'
_publ_section_title
;
 Two-dimensional hydrogen-bonded networks in crystals of diboronic
 acids
;
_journal_name_full               CrystEngComm
_journal_page_first              33
_journal_page_last               35
_journal_paper_doi               10.1039/b516402h
_journal_year                    2006
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C14 H12 B2 O4, 3(C4 H8 O2)'
_chemical_formula_sum            'C26 H36 B2 O10'
_chemical_formula_weight         530.17
_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                94.672(2)
_cell_angle_beta                 102.780(3)
_cell_angle_gamma                98.325(3)
_cell_formula_units_Z            1
_cell_length_a                   6.7104(4)
_cell_length_b                   7.4452(4)
_cell_length_c                   14.1376(8)
_cell_measurement_reflns_used    5344
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      3.23
_cell_volume                     676.83(7)
_computing_cell_refinement       'SMART (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Montel 200 Optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8385
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        1.63
_diffrn_standards_interval_time  1440
_diffrn_standards_number         33
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0725
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1556P)²+0.0764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1930
_refine_ls_wR_factor_ref         0.2043
_reflns_number_gt                2062
_reflns_number_total             2359
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b516402h.txt
_cod_data_source_block           jiw890
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (28
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (25
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (32 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7203218
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 0.3584(4) 0.4774(3) 0.61470(14) 0.0362(5) Uani 1 1 d . . .
O1 O 0.2945(2) 0.57211(17) 0.53760(8) 0.0378(4) Uani 1 1 d . . .
H1 H 0.198(4) 0.645(4) 0.542(2) 0.064(7) Uiso 1 1 d . . .
O2 O 0.5149(2) 0.38162(19) 0.61382(9) 0.0434(4) Uani 1 1 d . . .
H2 H 0.562(4) 0.385(4) 0.556(2) 0.078(9) Uiso 1 1 d . . .
C1 C 0.0300(3) 0.4973(2) 0.96262(12) 0.0316(5) Uani 1 1 d . . .
C2 C 0.1059(3) 0.4906(2) 0.87586(11) 0.0298(5) Uani 1 1 d . . .
C3 C -0.0085(3) 0.5380(2) 0.78935(12) 0.0316(4) Uani 1 1 d . . .
H3 H -0.1390 0.5748 0.7874 0.038 Uiso 1 1 calc . . .
C4 C 0.0692(3) 0.5314(2) 0.70569(12) 0.0328(5) Uani 1 1 d . . .
H4 H -0.0097 0.5634 0.6469 0.039 Uiso 1 1 calc . . .
C5 C 0.2621(3) 0.4783(2) 0.70676(12) 0.0334(5) Uani 1 1 d . . .
C6 C 0.3725(3) 0.4288(2) 0.79338(12) 0.0337(5) Uani 1 1 d . . .
H6 H 0.5025 0.3911 0.7953 0.040 Uiso 1 1 calc . . .
C7 C 0.2966(3) 0.4333(2) 0.87709(12) 0.0312(4) Uani 1 1 d . . .
H7 H 0.3738 0.3975 0.9353 0.037 Uiso 1 1 calc . . .
C10 C 0.1637(3) 0.0068(3) 0.16191(16) 0.0453(5) Uani 1 1 d . . .
H10A H 0.0371 0.0623 0.1443 0.054 Uiso 1 1 calc R . .
H10B H 0.1240 -0.1145 0.1826 0.054 Uiso 1 1 calc R . .
O10 O 0.3077(2) 0.11938(18) 0.24082(10) 0.0431(4) Uani 1 1 d . . .
C11 C 0.2534(3) -0.0169(3) 0.07359(14) 0.0449(5) Uani 1 1 d . . .
H11A H 0.1509 -0.0988 0.0207 0.054 Uiso 1 1 calc R . .
H11B H 0.2834 0.1031 0.0497 0.054 Uiso 1 1 calc R . .
C12 C 0.5825(3) 0.0233(3) 0.17479(15) 0.0440(5) Uani 1 1 d . . .
H12A H 0.6175 0.1451 0.1536 0.053 Uiso 1 1 calc R . .
H12B H 0.7115 -0.0290 0.1918 0.053 Uiso 1 1 calc R . .
O12 O 0.4383(2) -0.09211(17) 0.09731(9) 0.0414(4) Uani 1 1 d . . .
C13 C 0.4936(3) 0.0436(3) 0.26333(14) 0.0428(5) Uani 1 1 d . . .
H13A H 0.4639 -0.0775 0.2861 0.051 Uiso 1 1 calc R . .
H13B H 0.5964 0.1241 0.3167 0.051 Uiso 1 1 calc R . .
O13 O 0.0366(3) 0.82369(19) 0.51385(12) 0.0637(6) Uani 1 1 d . . .
C20 C 0.0533(9) 0.9071(6) 0.4230(3) 0.0406(10) Uani 0.50 1 d P . 1
H20A H 0.1453 0.8479 0.3891 0.049 Uiso 0.50 1 calc PR . 1
H20B H -0.0847 0.8962 0.3778 0.049 Uiso 0.50 1 calc PR . 1
C21 C -0.1414(9) 0.9018(6) 0.5425(3) 0.0434(10) Uani 0.50 1 d P . 1
H21A H -0.2607 0.8912 0.4856 0.052 Uiso 0.50 1 calc PR . 1
H21B H -0.1871 0.8385 0.5948 0.052 Uiso 0.50 1 calc PR . 1
C22 C -0.0148(7) 0.9466(5) 0.5911(3) 0.0308(8) Uani 0.50 1 d P . 2
H22A H 0.1101 1.0312 0.6290 0.037 Uiso 0.50 1 calc PR . 2
H22B H -0.0777 0.8751 0.6363 0.037 Uiso 0.50 1 calc PR . 2
C23 C 0.1692(7) 0.9502(5) 0.4678(3) 0.0271(7) Uani 0.50 1 d P . 2
H23A H 0.2380 0.8818 0.4250 0.033 Uiso 0.50 1 calc PR . 2
H23B H 0.2761 1.0343 0.5178 0.033 Uiso 0.50 1 calc PR . 2
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'
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 B1 O1 . . . 119.09(15) y
O2 B1 C5 . . . 117.82(16) y
O1 B1 C5 . . . 123.07(17) y
B1 O1 H1 . . . 118.0(17) ?
B1 O2 H2 . . . 113.0(17) ?
C1 C1 C2 2_567 . . 178.5(3) y
C3 C2 C7 . . . 119.44(14) y
C3 C2 C1 . . . 120.78(16) y
C7 C2 C1 . . . 119.77(15) y
C2 C3 C4 . . . 119.77(16) y
C2 C3 H3 . . . 120.1 ?
C4 C3 H3 . . . 120.1 ?
C3 C4 C5 . . . 121.22(16) y
C3 C4 H4 . . . 119.4 ?
C5 C4 H4 . . . 119.4 ?
C6 C5 C4 . . . 118.12(15) y
C6 C5 B1 . . . 119.46(17) y
C4 C5 B1 . . . 122.41(16) y
C7 C6 C5 . . . 121.40(17) y
C7 C6 H6 . . . 119.3 ?
C5 C6 H6 . . . 119.3 ?
C6 C7 C2 . . . 120.02(16) y
C6 C7 H7 . . . 120 ?
C2 C7 H7 . . . 120 ?
O10 C10 C11 . . . 111.58(16) y
O10 C10 H10A . . . 109.3 ?
C11 C10 H10A . . . 109.3 ?
O10 C10 H10B . . . 109.3 ?
C11 C10 H10B . . . 109.3 ?
H10A C10 H10B . . . 108 ?
C10 O10 C13 . . . 109.28(13) y
O12 C11 C10 . . . 110.58(16) y
O12 C11 H11A . . . 109.5 ?
C10 C11 H11A . . . 109.5 ?
O12 C11 H11B . . . 109.5 ?
C10 C11 H11B . . . 109.5 ?
H11A C11 H11B . . . 108.1 ?
O12 C12 C13 . . . 110.63(16) y
O12 C12 H12A . . . 109.5 ?
C13 C12 H12A . . . 109.5 ?
O12 C12 H12B . . . 109.5 ?
C13 C12 H12B . . . 109.5 ?
H12A C12 H12B . . . 108.1 ?
C12 O12 C11 . . . 109.27(14) y
O10 C13 C12 . . . 110.60(16) y
O10 C13 H13A . . . 109.5 ?
C12 C13 H13A . . . 109.5 ?
O10 C13 H13B . . . 109.5 ?
C12 C13 H13B . . . 109.5 ?
H13A C13 H13B . . . 108.1 ?
C23 O13 C22 . . . 103.6(2) y
C20 O13 C22 . . . 114.9(2) y
C23 O13 C21 . . . 114.6(2) y
C20 O13 C21 . . . 102.9(3) y
C21 C20 O13 2_576 . . 104.0(3) y
C21 C20 H20A 2_576 . . 111 ?
O13 C20 H20A . . . 111 ?
C21 C20 H20B 2_576 . . 111 ?
O13 C20 H20B . . . 111 ?
H20A C20 H20B . . . 109 ?
C20 C21 O13 2_576 . . 103.6(4) y
C20 C21 H21A 2_576 . . 111 ?
O13 C21 H21A . . . 111 ?
C20 C21 H21B 2_576 . . 111 ?
O13 C21 H21B . . . 111 ?
H21A C21 H21B . . . 109 ?
O13 C22 C23 . . 2_576 102.9(3) y
O13 C22 H22A . . . 111.2 ?
C23 C22 H22A 2_576 . . 111.2 ?
O13 C22 H22B . . . 111.2 ?
C23 C22 H22B 2_576 . . 111.2 ?
H22A C22 H22B . . . 109.1 ?
O13 C23 C22 . . 2_576 102.9(3) y
O13 C23 H23A . . . 111.2 ?
C22 C23 H23A 2_576 . . 111.2 ?
O13 C23 H23B . . . 111.2 ?
C22 C23 H23B 2_576 . . 111.2 ?
H23A C23 H23B . . . 109.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 O2 . . 1.354(2) y
B1 O1 . . 1.369(2) y
B1 C5 . . 1.576(2) y
O1 H1 . . 0.91(3) ?
O2 H2 . . 0.94(3) ?
C1 C1 . 2_567 1.211(3) y
C1 C2 . . 1.429(2) y
C2 C3 . . 1.394(3) y
C2 C7 . . 1.403(3) y
C3 C4 . . 1.394(2) y
C3 H3 . . 0.95 ?
C4 C5 . . 1.404(3) y
C4 H4 . . 0.95 ?
C5 C6 . . 1.391(3) y
C6 C7 . . 1.388(2) y
C6 H6 . . 0.95 ?
C7 H7 . . 0.95 ?
C10 O10 . . 1.420(2) y
C10 C11 . . 1.510(3) y
C10 H10a . . 0.99 ?
C10 H10b . . 0.99 ?
O10 C13 . . 1.426(2) y
C11 O12 . . 1.419(2) y
C11 H11a . . 0.99 ?
C11 H11b . . 0.99 ?
C12 O12 . . 1.418(2) y
C12 C13 . . 1.507(3) y
C12 H12a . . 0.99 ?
C12 H12b . . 0.99 ?
C13 H13a . . 0.99 ?
C13 H13b . . 0.99 ?
O13 C23 . . 1.489(4) y
O13 C20 . . 1.490(4) y
O13 C22 . . 1.498(3) y
O13 C21 . . 1.518(4) y
C20 C21 . 2_576 1.458(7) y
C20 H20a . . 0.99 ?
C20 H20b . . 0.99 ?
C21 C20 . 2_576 1.458(7) y
C21 H21a . . 0.99 ?
C21 H21b . . 0.99 ?
C22 C23 . 2_576 1.520(5) y
C22 H22a . . 0.99 ?
C22 H22b . . 0.99 ?
C23 C22 . 2_576 1.520(5) y
C23 H23a . . 0.99 ?
C23 H23b . . 0.99 ?
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
O1 H1 O13 0.91(3) 1.85(3) 2.7206(19) 159(3) .
O2 H2 O1 0.94(3) 1.82(3) 2.7458(15) 167(3) 2_666
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
C7 C2 C3 C4 . . . . -1.2(3) y
C1 C2 C3 C4 . . . . 179.67(16) y
C2 C3 C4 C5 . . . . -0.3(3) y
C3 C4 C5 C6 . . . . 1.2(3) y
C3 C4 C5 B1 . . . . -177.35(16) y
O2 B1 C5 C6 . . . . 18.1(3) y
O1 B1 C5 C6 . . . . -160.2(2) y
O2 B1 C5 C4 . . . . -163.29(18) y
O1 B1 C5 C4 . . . . 18.4(3) y
C4 C5 C6 C7 . . . . -0.7(3) y
B1 C5 C6 C7 . . . . 177.91(16) y
C5 C6 C7 C2 . . . . -0.7(3) y
C3 C2 C7 C6 . . . . 1.7(3) y
C1 C2 C7 C6 . . . . -179.15(15) y
C11 C10 O10 C13 . . . . -56.4(2) y
O10 C10 C11 O12 . . . . 57.5(2) y
C13 C12 O12 C11 . . . . 58.9(2) y
C10 C11 O12 C12 . . . . -57.7(2) y
C10 O10 C13 C12 . . . . 57.1(2) y
O12 C12 C13 O10 . . . . -59.4(2) y
C23 O13 C20 C21 . . . 2_576 -42.8(4) y
C22 O13 C20 C21 . . . 2_576 34.8(5) y
C21 O13 C20 C21 . . . 2_576 72.2(5) y
C23 O13 C21 C20 . . . 2_576 -37.3(5) y
C20 O13 C21 C20 . . . 2_576 -71.9(5) y
C22 O13 C21 C20 . . . 2_576 42.6(4) y
C23 O13 C22 C23 . . . 2_576 73.1(4) y
C20 O13 C22 C23 . . . 2_576 38.3(5) y
C21 O13 C22 C23 . . . 2_576 -39.8(3) y
C20 O13 C23 C22 . . . 2_576 41.2(3) y
C22 O13 C23 C22 . . . 2_576 -73.1(4) y
C21 O13 C23 C22 . . . 2_576 -35.3(5) y
