#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/87/4508707.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_4508707
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
_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                83.340(4)
_cell_angle_beta                 88.191(4)
_cell_angle_gamma                68.800(3)
_cell_formula_units_Z            1
_cell_length_a                   5.8840(11)
_cell_length_b                   6.1283(12)
_cell_length_c                   15.614(3)
_cell_measurement_reflns_used    3238
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      26.378
_cell_measurement_theta_min      2.627
_cell_volume                     521.35(17)
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4189
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.63
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             226
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0359
_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)+(0.0495P)²+0.0683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                1621
_reflns_number_total             1826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0601148sup1.cif
_cod_data_source_block           2
_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_original_cell_volume        521.36(17)
_cod_database_code               4508707
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 0.4841(3) 0.6057(3) 0.38062(9) 0.0226(3) Uani 1 1 d .
O1 O 0.28277(16) 0.79990(15) 0.39780(5) 0.0236(3) Uani 1 1 d .
O2 O 0.69327(16) 0.60127(15) 0.42153(6) 0.0245(3) Uani 1 1 d .
O3 O 0.48577(16) -0.05887(16) 0.15300(6) 0.0272(3) Uani 1 1 d .
C1 C 0.2401(2) 1.1254(2) 0.48555(8) 0.0226(3) Uani 1 1 d .
H1 H 0.0702 1.2077 0.4763 0.028(4) Uiso 1 1 calc R
C2 C 0.3700(2) 0.9201(2) 0.45082(8) 0.0211(3) Uani 1 1 d .
C3 C 0.6175(2) 0.8010(2) 0.46485(8) 0.0211(3) Uani 1 1 d .
C4 C 0.4845(2) 0.4186(2) 0.32316(8) 0.0223(3) Uani 1 1 d .
C5 C 0.2725(2) 0.4244(2) 0.28281(8) 0.0250(3) Uani 1 1 d .
H5 H 0.1209 0.5428 0.2938 0.032(4) Uiso 1 1 calc R
C6 C 0.2792(2) 0.2626(2) 0.22772(8) 0.0246(3) Uani 1 1 d .
H6 H 0.1331 0.2713 0.2008 0.031(4) Uiso 1 1 calc R
C7 C 0.4992(2) 0.0856(2) 0.21114(8) 0.0225(3) Uani 1 1 d .
C8 C 0.7104(2) 0.0688(2) 0.25348(8) 0.0240(3) Uani 1 1 d .
H8 H 0.8601 -0.0551 0.2450 0.027(4) Uiso 1 1 calc R
C9 C 0.7001(2) 0.2350(2) 0.30818(8) 0.0237(3) Uani 1 1 d .
H9 H 0.8454 0.2232 0.3364 0.025(4) Uiso 1 1 calc R
C10 C 0.7055(2) -0.2475(2) 0.13201(9) 0.0252(3) Uani 1 1 d .
H10 H 0.7963 -0.3324 0.1863 0.023(3) Uiso 1 1 calc R
C11 C 0.8683(3) -0.1541(3) 0.07377(10) 0.0363(4) Uani 1 1 d .
H11A H 0.7850 -0.0843 0.0184 0.048(5) Uiso 1 1 calc R
H11B H 1.0207 -0.2836 0.0642 0.046(5) Uiso 1 1 calc R
H11C H 0.9044 -0.0339 0.1010 0.047(5) Uiso 1 1 calc R
C12 C 0.6202(3) -0.4113(2) 0.08856(9) 0.0322(4) Uani 1 1 d .
H12A H 0.5107 -0.4639 0.1270 0.044(4) Uiso 1 1 calc R
H12B H 0.7612 -0.5482 0.0754 0.034(4) Uiso 1 1 calc R
H12C H 0.5330 -0.3286 0.0350 0.042(4) 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
O1 B1 O2 111.31(12) . .
O1 B1 C4 125.68(13) . .
O2 B1 C4 123.01(12) . .
B1 O1 C2 105.24(10) . .
C3 O2 B1 105.10(10) . .
C7 O3 C10 119.02(10) . .
C2 C1 C3 112.97(12) . 2_676
C2 C1 H1 123.5 . .
C3 C1 H1 123.5 2_676 .
C1 C2 C3 123.13(12) . .
C1 C2 O1 127.64(12) . .
C3 C2 O1 109.23(11) . .
C1 C3 C2 123.90(12) 2_676 .
C1 C3 O2 126.98(11) 2_676 .
C2 C3 O2 109.12(11) . .
C9 C4 C5 116.99(12) . .
C9 C4 B1 120.60(12) . .
C5 C4 B1 122.40(12) . .
C6 C5 C4 121.47(12) . .
C6 C5 H5 119.3 . .
C4 C5 H5 119.3 . .
C5 C6 C7 120.41(12) . .
C5 C6 H6 119.8 . .
C7 C6 H6 119.8 . .
O3 C7 C8 125.36(12) . .
O3 C7 C6 115.34(12) . .
C8 C7 C6 119.30(12) . .
C9 C8 C7 119.32(12) . .
C9 C8 H8 120.3 . .
C7 C8 H8 120.3 . .
C8 C9 C4 122.39(13) . .
C8 C9 H9 118.8 . .
C4 C9 H9 118.8 . .
O3 C10 C12 105.45(11) . .
O3 C10 C11 111.28(11) . .
C12 C10 C11 111.51(11) . .
O3 C10 H10 109.5 . .
C12 C10 H10 109.5 . .
C11 C10 H10 109.5 . .
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 O1 1.3878(17) .
B1 O2 1.3949(18) .
B1 C4 1.535(2) .
O1 C2 1.3900(15) .
O2 C3 1.3900(15) .
O3 C7 1.3622(15) .
O3 C10 1.4476(15) .
C1 C2 1.3779(17) .
C1 C3 1.3786(18) 2_676
C1 H1 0.9500 .
C2 C3 1.3844(18) .
C3 C1 1.3786(18) 2_676
C4 C9 1.3927(18) .
C4 C5 1.4023(19) .
C5 C6 1.3760(18) .
C5 H5 0.9500 .
C6 C7 1.3956(18) .
C6 H6 0.9500 .
C7 C8 1.3911(19) .
C8 C9 1.3871(18) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C12 1.5051(19) .
C10 C11 1.5139(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
O2 B1 O1 C2 0.17(14) . .
C4 B1 O1 C2 -178.84(12) . .
O1 B1 O2 C3 -0.41(14) . .
C4 B1 O2 C3 178.64(12) . .
C3 C1 C2 C3 0.2(2) 2_676 .
C3 C1 C2 O1 -179.63(11) 2_676 .
B1 O1 C2 C1 179.97(12) . .
B1 O1 C2 C3 0.14(13) . .
C1 C2 C3 C1 -0.2(2) . 2_676
O1 C2 C3 C1 179.64(11) . 2_676
C1 C2 C3 O2 179.76(11) . .
O1 C2 C3 O2 -0.40(14) . .
B1 O2 C3 C1 -179.55(12) . 2_676
B1 O2 C3 C2 0.48(13) . .
O1 B1 C4 C9 177.78(12) . .
O2 B1 C4 C9 -1.1(2) . .
O1 B1 C4 C5 -1.5(2) . .
O2 B1 C4 C5 179.62(12) . .
C9 C4 C5 C6 -2.96(19) . .
B1 C4 C5 C6 176.32(12) . .
C4 C5 C6 C7 0.6(2) . .
C10 O3 C7 C8 0.07(19) . .
C10 O3 C7 C6 -179.96(11) . .
C5 C6 C7 O3 -177.48(11) . .
C5 C6 C7 C8 2.5(2) . .
O3 C7 C8 C9 176.93(11) . .
C6 C7 C8 C9 -3.0(2) . .
C7 C8 C9 C4 0.6(2) . .
C5 C4 C9 C8 2.39(19) . .
B1 C4 C9 C8 -176.90(12) . .
C7 O3 C10 C12 163.94(10) . .
C7 O3 C10 C11 -75.00(14) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102387729
