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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/52/4505239.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_4505239
loop_
_publ_author_name
'Bhosekar, Gaurav'
'Murali, Chebrolu'
'Gonnade, Rajesh G.'
'Shashidhar, Mysore S.'
'Bhadbhade, Mohan M.'
_publ_section_title
;
 Identical Molecular Strings Woven Differently by Intermolecular
 Interactions in Dimorphs ofmyo-Inositol 1,3,5-Orthobenzoate
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1977
_journal_paper_doi               10.1021/cg050272j
_journal_volume                  5
_journal_year                    2005
_chemical_formula_moiety         'C13 H14 O6'
_chemical_formula_sum            'C13 H14 O6'
_chemical_formula_weight         266.24
_chemical_name_systematic        'myo-inositol 1,3,5-orthobenzoate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 115.897(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2323(9)
_cell_length_b                   33.014(5)
_cell_length_c                   6.4077(9)
_cell_measurement_reflns_used    4153
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.573
_cell_measurement_theta_min      2.467
_cell_volume                     1186.0(3)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'phi and Omega Scan'
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8778
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_correction_T_min  0.9421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'bruker sadabs'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0435
_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)+(0.0419P)²+0.4281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                2078
_reflns_number_total             2203
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050272jsi20050616_031459.cif
_cod_data_source_block           FormI
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4505239
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O1 O 0.31596(19) 0.11178(3) 0.46109(19) 0.0361(3) Uani 1 1 d
O2 O 0.1533(2) 0.03015(4) 0.34205(19) 0.0370(3) Uani 1 1 d
O3 O -0.00786(18) 0.09499(3) 0.53128(19) 0.0330(3) Uani 1 1 d
O4 O 0.3692(2) 0.03917(4) 1.0577(2) 0.0478(4) Uani 1 1 d
O5 O 0.2832(2) 0.13865(4) 0.7795(2) 0.0418(3) Uani 1 1 d
O6 O 0.7465(2) 0.05912(4) 0.9796(2) 0.0466(3) Uani 1 1 d
C1 C 0.4535(3) 0.07771(5) 0.5926(3) 0.0335(4) Uani 1 1 d
C2 C 0.2811(3) 0.04379(5) 0.5755(3) 0.0302(4) Uani 1 1 d
C3 C 0.1119(3) 0.06009(5) 0.6684(3) 0.0321(4) Uani 1 1 d
C4 C 0.2457(3) 0.07323(5) 0.9200(3) 0.0382(4) Uani 1 1 d
C5 C 0.4206(3) 0.10620(6) 0.9304(3) 0.0408(4) Uani 1 1 d
C6 C 0.5980(3) 0.09112(6) 0.8435(3) 0.0390(4) Uani 1 1 d
C7 C 0.1573(3) 0.12583(5) 0.5474(3) 0.0342(4) Uani 1 1 d
C8 C 0.0139(3) 0.16066(5) 0.4012(3) 0.0420(4) Uani 1 1 d
C9 C 0.0503(5) 0.17538(7) 0.2193(4) 0.0633(6) Uani 1 1 d
C10 C -0.0930(7) 0.20630(8) 0.0818(5) 0.0882(9) Uani 1 1 d
C11 C -0.2686(6) 0.22229(8) 0.1271(6) 0.0908(10) Uani 1 1 d
C12 C -0.3090(5) 0.20743(8) 0.3044(7) 0.0857(9) Uani 1 1 d
C13 C -0.1682(4) 0.17659(7) 0.4427(5) 0.0641(6) Uani 1 1 d
H1 H 0.554(3) 0.0705(5) 0.519(3) 0.033(4) Uiso 1 1 d
H2 H 0.367(3) 0.0203(5) 0.665(3) 0.022(4) Uiso 1 1 d
H3 H -0.012(3) 0.0405(5) 0.650(3) 0.031(4) Uiso 1 1 d
H4 H 0.131(3) 0.0844(5) 0.971(3) 0.033(4) Uiso 1 1 d
H5 H 0.502(3) 0.1176(6) 1.085(3) 0.041(5) Uiso 1 1 d
H6 H 0.702(3) 0.1134(6) 0.845(3) 0.038(5) Uiso 1 1 d
H9 H 0.181(5) 0.1647(9) 0.194(5) 0.086(9) Uiso 1 1 d
H10 H -0.068(6) 0.2150(9) -0.049(6) 0.110(11) Uiso 1 1 d
H11 H -0.360(5) 0.2434(9) 0.032(5) 0.100(9) Uiso 1 1 d
H12 H -0.430(6) 0.2172(9) 0.342(6) 0.109(11) Uiso 1 1 d
H13 H -0.189(5) 0.1663(8) 0.572(5) 0.080(8) Uiso 1 1 d
H2A H 0.048(4) 0.0481(7) 0.271(4) 0.054(6) Uiso 1 1 d
H4A H 0.309(4) 0.0341(7) 1.150(5) 0.071(8) Uiso 1 1 d
H6A H 0.666(5) 0.0443(8) 1.022(4) 0.071(8) Uiso 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'
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
C7 O1 C1 111.60(12) . .
O3 O3 C7 0(10) 1 .
O3 O3 C3 0(10) 1 .
C7 O3 C3 111.26(11) . .
O4 O4 C4 0(10) 1 .
C7 O5 C5 112.15(12) . .
O1 C1 C2 108.13(12) . .
O1 C1 C6 108.43(13) . .
C2 C1 C6 111.25(13) . .
O2 C2 C3 110.96(12) . .
O2 C2 C1 111.16(13) . .
C3 C2 C1 107.49(13) . .
O3 C3 O3 0.00(10) 1 .
O3 C3 C2 107.88(12) 1 .
O3 C3 C2 107.88(12) . .
O3 C3 C4 108.44(13) 1 .
O3 C3 C4 108.44(13) . .
C2 C3 C4 111.32(13) . .
O4 C4 O4 0.00(12) 1 .
O4 C4 C3 109.19(14) 1 .
O4 C4 C3 109.19(14) . .
O4 C4 C5 110.71(14) 1 .
O4 C4 C5 110.71(14) . .
C3 C4 C5 107.57(13) . .
O5 C5 C4 107.29(13) . .
O5 C5 C6 108.05(14) . .
C4 C5 C6 111.77(15) . .
O6 C6 C5 113.56(15) . .
O6 C6 C1 110.92(14) . .
C5 C6 C1 106.95(13) . .
O1 C7 O5 110.56(12) . .
O1 C7 O3 110.32(12) . 1
O5 C7 O3 110.13(13) . 1
O1 C7 O3 110.32(12) . .
O5 C7 O3 110.13(13) . .
O3 C7 O3 0.00(9) 1 .
O1 C7 C8 109.61(13) . .
O5 C7 C8 109.42(13) . .
O3 C7 C8 106.72(12) 1 .
O3 C7 C8 106.72(12) . .
C9 C8 C13 119.0(2) . .
C9 C8 C7 121.73(18) . .
C13 C8 C7 119.13(18) . .
C8 C9 C10 120.0(3) . .
C11 C10 C9 120.4(3) . .
C10 C11 C12 120.0(3) . .
C11 C12 C13 120.3(3) . .
C8 C13 C12 120.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.406(2) .
O1 C1 1.4418(19) .
O2 C2 1.4263(19) .
O3 O3 0.000(2) 1
O3 C7 1.4192(19) .
O3 C3 1.4437(18) .
O4 O4 0.000(4) 1
O4 C4 1.429(2) .
O5 C7 1.409(2) .
O5 C5 1.447(2) .
O6 C6 1.424(2) .
C1 C2 1.522(2) .
C1 C6 1.526(2) .
C2 C3 1.518(2) .
C3 O3 1.4437(18) 1
C3 C4 1.519(2) .
C4 O4 1.429(2) 1
C4 C5 1.521(3) .
C5 C6 1.523(3) .
C7 O3 1.4192(19) 1
C7 C8 1.506(2) .
C8 C9 1.370(3) .
C8 C13 1.378(3) .
C9 C10 1.389(3) .
C10 C11 1.356(5) .
C11 C12 1.358(5) .
C12 C13 1.383(3) .
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
C1 H1 O3 0.964(18) 2.815(18) 3.5918(19) 138.2(13) 1_655
C2 H2 O4 0.975(16) 2.675(17) 3.647(2) 174.3(12) 3_657
C4 H4 O6 0.977(18) 2.564(17) 3.329(2) 135.2(13) 1_455
C3 H3 O2 0.973(18) 2.502(18) 3.393(2) 152.1(13) 3_556
O6 H6A O4 0.83(3) 1.96(3) 2.690(2) 146(2) 1
O2 H2A O3 0.85(2) 2.41(2) 2.8507(16) 112.6(17) 1
O2 H2A O6 0.85(2) 2.02(2) 2.7557(17) 144(2) 1_454
O4 H4A O2 0.85(3) 1.87(3) 2.7131(18) 172(2) 1_556
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
C7 O1 C1 C2 60.21(16) . .
C7 O1 C1 C6 -60.54(16) . .
O1 C1 C2 O2 63.46(16) . .
C6 C1 C2 O2 -177.57(13) . .
O1 C1 C2 C3 -58.15(15) . .
C6 C1 C2 C3 60.82(16) . .
C7 O3 C3 O3 0.0(3) . 1
O3 O3 C3 C2 0.0(2) 1 .
C7 O3 C3 C2 -60.65(16) . .
O3 O3 C3 C4 0.0(2) 1 .
C7 O3 C3 C4 60.03(16) . .
O2 C2 C3 O3 -63.28(16) . 1
C1 C2 C3 O3 58.46(15) . 1
O2 C2 C3 O3 -63.28(16) . .
C1 C2 C3 O3 58.46(15) . .
O2 C2 C3 C4 177.86(13) . .
C1 C2 C3 C4 -60.40(16) . .
O4 O4 C4 C3 0.0(4) 1 .
O4 O4 C4 C5 0.0(4) 1 .
O3 C3 C4 O4 -178.87(12) 1 1
O3 C3 C4 O4 -178.87(12) . 1
C2 C3 C4 O4 -60.35(17) . 1
O3 C3 C4 O4 -178.87(12) 1 .
O3 C3 C4 O4 -178.87(12) . .
C2 C3 C4 O4 -60.35(17) . .
O3 C3 C4 C5 -58.68(16) 1 .
O3 C3 C4 C5 -58.68(16) . .
C2 C3 C4 C5 59.85(17) . .
C7 O5 C5 C4 -60.81(17) . .
C7 O5 C5 C6 59.85(17) . .
O4 C4 C5 O5 177.54(12) 1 .
O4 C4 C5 O5 177.54(12) . .
C3 C4 C5 O5 58.32(17) . .
O4 C4 C5 C6 59.27(18) 1 .
O4 C4 C5 C6 59.27(18) . .
C3 C4 C5 C6 -59.96(17) . .
O5 C5 C6 O6 179.51(13) . .
C4 C5 C6 O6 -62.66(18) . .
O5 C5 C6 C1 -57.80(17) . .
C4 C5 C6 C1 60.02(18) . .
O1 C1 C6 O6 -177.22(13) . .
C2 C1 C6 O6 63.99(17) . .
O1 C1 C6 C5 58.45(17) . .
C2 C1 C6 C5 -60.34(18) . .
C1 O1 C7 O5 60.68(16) . .
C1 O1 C7 O3 -61.38(15) . 1
C1 O1 C7 O3 -61.38(15) . .
C1 O1 C7 C8 -178.61(12) . .
C5 O5 C7 O1 -60.57(17) . .
C5 O5 C7 O3 61.60(17) . 1
C5 O5 C7 O3 61.60(17) . .
C5 O5 C7 C8 178.61(14) . .
O3 O3 C7 O1 0.00(6) 1 .
C3 O3 C7 O1 61.65(16) . .
O3 O3 C7 O5 0.00(6) 1 .
C3 O3 C7 O5 -60.66(16) . .
C3 O3 C7 O3 0.0(13) . 1
O3 O3 C7 C8 0.00(4) 1 .
C3 O3 C7 C8 -179.34(12) . .
O1 C7 C8 C9 -2.0(2) . .
O5 C7 C8 C9 119.4(2) . .
O3 C7 C8 C9 -121.49(19) 1 .
O3 C7 C8 C9 -121.49(19) . .
O1 C7 C8 C13 174.07(17) . .
O5 C7 C8 C13 -64.5(2) . .
O3 C7 C8 C13 54.6(2) 1 .
O3 C7 C8 C13 54.6(2) . .
C13 C8 C9 C10 0.9(3) . .
C7 C8 C9 C10 177.0(2) . .
C8 C9 C10 C11 0.4(4) . .
C9 C10 C11 C12 -1.6(5) . .
C10 C11 C12 C13 1.4(5) . .
C9 C8 C13 C12 -1.0(3) . .
C7 C8 C13 C12 -177.2(2) . .
C11 C12 C13 C8 -0.1(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11694628
