#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:18:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179623 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/87/4508708.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4508708
loop_
_publ_author_name
'Niu, Weijun'
'Smith, Mark D.'
'Lavigne, John J.'
_publ_section_title
;
 Substituent Effects on the Structure and Supramolecular Assembly of
 Bis(dioxaborole)s Derived from 1,2,4,5-Tetrahydroxybenzene
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1274
_journal_paper_doi               10.1021/cg0601148
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C24 H24 B2 O6'
_chemical_formula_sum            'C24 H24 B2 O6'
_chemical_formula_weight         430.05
_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                95.9190(10)
_cell_angle_beta                 104.6830(10)
_cell_angle_gamma                96.6790(10)
_cell_formula_units_Z            1
_cell_length_a                   6.3967(5)
_cell_length_b                   6.9843(6)
_cell_length_c                   12.2171(10)
_cell_measurement_reflns_used    3927
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      26.372
_cell_measurement_theta_min      2.965
_cell_volume                     519.39(7)
_computing_cell_refinement       'SAINT+ NT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART NT V5.625 (Bruker, 1998)'
_computing_data_reduction        'SAINT+ NT V6.22'
_computing_molecular_graphics    'SHELXTL V6.1 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0304
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4669
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             226
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.044(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0362
_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)+(0.0461P)²+0.1557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                1733
_reflns_number_total             1841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0601148sup1.cif
_cod_data_source_block           3
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4508708
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
B1 B 0.4564(2) 0.3586(2) 0.12357(12) 0.0232(3) Uani 1 1 d .
C1 C -0.0997(2) 0.29744(19) -0.03704(10) 0.0224(3) Uani 1 1 d .
H1 H -0.1644 0.1654 -0.0614 0.017(3) Uiso 1 1 calc R
C2 C 0.1157(2) 0.35412(18) 0.02515(10) 0.0214(3) Uani 1 1 d .
C3 C 0.2109(2) 0.54665(18) 0.06007(10) 0.0211(3) Uani 1 1 d .
C4 C 0.6696(2) 0.28589(19) 0.18277(11) 0.0228(3) Uani 1 1 d .
C5 C 0.6787(2) 0.0874(2) 0.17494(12) 0.0289(3) Uani 1 1 d .
H5 H 0.5519 -0.0026 0.1362 0.038(4) Uiso 1 1 calc R
C6 C 0.8716(2) 0.0200(2) 0.22333(13) 0.0314(3) Uani 1 1 d .
H6 H 0.8765 -0.1161 0.2172 0.035(4) Uiso 1 1 calc R
C7 C 1.0569(2) 0.1487(2) 0.28043(12) 0.0271(3) Uani 1 1 d .
H7 H 1.1886 0.1012 0.3134 0.034(4) Uiso 1 1 calc R
C8 C 1.0508(2) 0.34814(19) 0.28981(10) 0.0225(3) Uani 1 1 d .
C9 C 0.8580(2) 0.41651(18) 0.24152(10) 0.0222(3) Uani 1 1 d .
H9 H 0.8534 0.5526 0.2482 0.020(3) Uiso 1 1 calc R
C10 C 1.2570(2) 0.66982(18) 0.36738(11) 0.0251(3) Uani 1 1 d .
H10 H 1.1787 0.7179 0.2961 0.022(3) Uiso 1 1 calc R
C11 C 1.1540(2) 0.7265(2) 0.46251(12) 0.0329(4) Uani 1 1 d .
H11A H 1.0027 0.6609 0.4428 0.040(4) Uiso 1 1 calc R
H11B H 1.1558 0.8678 0.4726 0.039(4) Uiso 1 1 calc R
H11C H 1.2369 0.6876 0.5337 0.041(5) Uiso 1 1 calc R
C12 C 1.4971(2) 0.7503(2) 0.39714(12) 0.0313(3) Uani 1 1 d .
H12A H 1.5738 0.7045 0.4674 0.041(5) Uiso 1 1 calc R
H12B H 1.5153 0.8929 0.4086 0.040(4) Uiso 1 1 calc R
H12C H 1.5580 0.7058 0.3347 0.047(5) Uiso 1 1 calc R
O1 O 0.26767(14) 0.23403(13) 0.06376(7) 0.0237(2) Uani 1 1 d .
O2 O 0.42751(14) 0.55242(13) 0.12058(7) 0.0235(2) Uani 1 1 d .
O3 O 1.24634(15) 0.46101(13) 0.34594(8) 0.0289(3) Uani 1 1 d .
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
O1 B1 O2 111.39(11) . .
O1 B1 C4 123.01(12) . .
O2 B1 C4 125.59(12) . .
C2 C1 C3 112.86(12) . 2_565
C2 C1 H1 123.6 . .
C3 C1 H1 123.6 2_565 .
O1 C2 C1 126.99(11) . .
O1 C2 C3 109.30(11) . .
C1 C2 C3 123.70(12) . .
C1 C3 C2 123.44(12) 2_565 .
C1 C3 O2 127.58(12) 2_565 .
C2 C3 O2 108.98(11) . .
C5 C4 C9 119.00(12) . .
C5 C4 B1 119.61(12) . .
C9 C4 B1 121.35(12) . .
C6 C5 C4 120.33(13) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C7 C6 C5 120.54(13) . .
C7 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
C6 C7 C8 120.02(13) . .
C6 C7 H7 120.0 . .
C8 C7 H7 120.0 . .
O3 C8 C9 125.76(12) . .
O3 C8 C7 114.52(11) . .
C9 C8 C7 119.70(12) . .
C8 C9 C4 120.40(12) . .
C8 C9 H9 119.8 . .
C4 C9 H9 119.8 . .
O3 C10 C12 105.32(10) . .
O3 C10 C11 110.98(11) . .
C12 C10 C11 112.30(11) . .
O3 C10 H10 109.4 . .
C12 C10 H10 109.4 . .
C11 C10 H10 109.4 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C2 O1 B1 105.24(10) . .
C3 O2 B1 105.04(10) . .
C8 O3 C10 119.54(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 O1 1.3877(17) .
B1 O2 1.3901(17) .
B1 C4 1.542(2) .
C1 C2 1.3830(18) .
C1 C3 1.3831(18) 2_565
C1 H1 0.9500 .
C2 O1 1.3822(15) .
C2 C3 1.3859(18) .
C3 C1 1.3830(18) 2_565
C3 O2 1.3889(15) .
C4 C5 1.3889(19) .
C4 C9 1.4036(18) .
C5 C6 1.385(2) .
C5 H5 0.9500 .
C6 C7 1.379(2) .
C6 H6 0.9500 .
C7 C8 1.3916(19) .
C7 H7 0.9500 .
C8 O3 1.3712(15) .
C8 C9 1.3870(19) .
C9 H9 0.9500 .
C10 O3 1.4454(16) .
C10 C12 1.5102(19) .
C10 C11 1.5152(19) .
C10 H10 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
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_4
C3 C1 C2 O1 178.43(11) 2_565 .
C3 C1 C2 C3 -0.47(19) 2_565 .
O1 C2 C3 C1 -178.55(11) . 2_565
C1 C2 C3 C1 0.5(2) . 2_565
O1 C2 C3 O2 0.80(13) . .
C1 C2 C3 O2 179.87(11) . .
O1 B1 C4 C5 1.5(2) . .
O2 B1 C4 C5 -177.22(12) . .
O1 B1 C4 C9 179.33(11) . .
O2 B1 C4 C9 0.6(2) . .
C9 C4 C5 C6 -0.7(2) . .
B1 C4 C5 C6 177.16(12) . .
C4 C5 C6 C7 0.4(2) . .
C5 C6 C7 C8 0.0(2) . .
C6 C7 C8 O3 -178.45(12) . .
C6 C7 C8 C9 0.0(2) . .
O3 C8 C9 C4 177.87(11) . .
C7 C8 C9 C4 -0.38(19) . .
C5 C4 C9 C8 0.75(19) . .
B1 C4 C9 C8 -177.11(11) . .
C1 C2 O1 B1 -178.56(12) . .
C3 C2 O1 B1 0.46(13) . .
O2 B1 O1 C2 -1.59(14) . .
C4 B1 O1 C2 179.54(12) . .
C1 C3 O2 B1 177.61(13) 2_565 .
C2 C3 O2 B1 -1.71(13) . .
O1 B1 O2 C3 2.06(13) . .
C4 B1 O2 C3 -179.11(12) . .
C9 C8 O3 C10 5.62(19) . .
C7 C8 O3 C10 -176.05(11) . .
C12 C10 O3 C8 -163.88(11) . .
C11 C10 O3 C8 74.36(14) . .
