#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/16/4501673.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_4501673
loop_
_publ_author_name
'Sarma, Bipul'
'Sanphui, Palash'
'Nangia, Ashwini'
_publ_section_title
;
 Polymorphism in Isomeric Dihydroxybenzoic Acids
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2388
_journal_paper_doi               10.1021/cg100220z
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C7 H6 O4'
_chemical_formula_sum            'C7 H6 O4'
_chemical_formula_weight         154.12
_chemical_name_common            3,5-Dihydroxybenzoicacid
_chemical_name_systematic
; 
 3,5-Dihydroxybenzoicacid 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 116.770(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            24
_cell_length_a                   14.101(2)
_cell_length_b                   22.433(4)
_cell_length_c                   14.161(2)
_cell_measurement_reflns_used    3846
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.80
_cell_measurement_theta_min      2.43
_cell_volume                     3999.4(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0759
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20096
_diffrn_reflns_theta_full        26.08
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         3858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.0964
_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)+(0.0953P)²+15.1728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2170
_refine_ls_wR_factor_ref         0.2406
_reflns_number_gt                2564
_reflns_number_total             3858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100220z_si_002.cif
_cod_data_source_block           3,5-DHBAsublimed_M
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3999.5(11)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               4501673
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags
O2 O 0.0804(3) 0.36717(14) 0.3809(3) 0.0506(10) Uani 1 1 d .
O1 O -0.0836(3) 0.36510(14) 0.3656(3) 0.0405(9) Uani 1 1 d .
O3 O 0.1890(3) 0.15362(15) 0.4094(3) 0.0399(9) Uani 1 1 d .
C5 C 0.0170(3) 0.15134(18) 0.4044(4) 0.0284(10) Uani 1 1 d .
H5 H 0.0204 0.1100 0.4103 0.034 Uiso 1 1 calc R
O4 O -0.1489(3) 0.14693(14) 0.4031(3) 0.0446(10) Uani 1 1 d .
C2 C 0.0062(4) 0.27369(18) 0.3834(3) 0.0267(10) Uani 1 1 d .
C3 C 0.0957(4) 0.24427(19) 0.3916(4) 0.0282(10) Uani 1 1 d .
H3 H 0.1517 0.2653 0.3900 0.034 Uiso 1 1 calc R
C7 C -0.0790(4) 0.24262(18) 0.3865(4) 0.0276(10) Uani 1 1 d .
H7 H -0.1389 0.2627 0.3812 0.033 Uiso 1 1 calc R
C1 C 0.0016(4) 0.34017(19) 0.3767(4) 0.0285(10) Uani 1 1 d .
C4 C 0.1002(3) 0.18275(18) 0.4022(3) 0.0247(10) Uani 1 1 d .
C6 C -0.0709(3) 0.18137(18) 0.3977(4) 0.0271(10) Uani 1 1 d .
O12 O 0.6757(3) 0.20081(14) 0.1564(3) 0.0395(9) Uani 1 1 d .
O10 O 0.5746(3) -0.01658(14) 0.1263(3) 0.0458(10) Uani 1 1 d .
O9 O 0.4118(3) -0.01537(15) 0.1150(3) 0.0515(11) Uani 1 1 d .
O11 O 0.3190(3) 0.19930(15) 0.1033(3) 0.0393(9) Uani 1 1 d .
C19 C 0.4981(4) 0.19996(18) 0.1274(4) 0.0287(10) Uani 1 1 d .
H19 H 0.4999 0.2414 0.1305 0.034 Uiso 1 1 calc R
C16 C 0.4936(4) 0.07646(19) 0.1183(4) 0.0302(10) Uani 1 1 d .
C21 C 0.5856(4) 0.10692(18) 0.1333(4) 0.0298(11) Uani 1 1 d .
H21 H 0.6456 0.0862 0.1405 0.036 Uiso 1 1 calc R
C17 C 0.4045(3) 0.10779(18) 0.1093(4) 0.0268(10) Uani 1 1 d .
H17 H 0.3438 0.0875 0.1011 0.032 Uiso 1 1 calc R
C18 C 0.4073(4) 0.16922(18) 0.1126(4) 0.0280(10) Uani 1 1 d .
C20 C 0.5860(4) 0.16808(18) 0.1374(4) 0.0262(10) Uani 1 1 d .
C15 C 0.4949(4) 0.01057(19) 0.1200(4) 0.0321(11) Uani 1 1 d .
O7 O 0.3422(3) 0.53247(14) 0.0811(3) 0.0423(10) Uani 1 1 d .
C12 C 0.3485(4) 0.53020(18) 0.2484(4) 0.0284(10) Uani 1 1 d .
H12 H 0.3525 0.5716 0.2497 0.034 Uiso 1 1 calc R
O5 O 0.3211(3) 0.31802(15) 0.3205(3) 0.0441(10) Uani 1 1 d .
O8 O 0.3508(3) 0.52831(14) 0.4190(3) 0.0448(10) Uani 1 1 d .
O6 O 0.3414(3) 0.31184(14) 0.1738(3) 0.0493(10) Uani 1 1 d .
C13 C 0.3441(4) 0.49891(18) 0.1630(3) 0.0260(10) Uani 1 1 d .
C10 C 0.3404(4) 0.43783(18) 0.3306(4) 0.0341(12) Uani 1 1 d .
H10 H 0.3372 0.4173 0.3861 0.041 Uiso 1 1 calc R
C9 C 0.3389(4) 0.40746(19) 0.2445(4) 0.0297(10) Uani 1 1 d .
C11 C 0.3470(4) 0.49946(18) 0.3320(3) 0.0275(10) Uani 1 1 d .
C14 C 0.3404(4) 0.43786(18) 0.1599(4) 0.0283(10) Uani 1 1 d .
H14 H 0.3390 0.4173 0.1023 0.034 Uiso 1 1 calc R
C8 C 0.3340(4) 0.34108(19) 0.2415(4) 0.0314(11) Uani 1 1 d .
H12C H 0.713(3) 0.1862(18) 0.134(3) 0.013(11) Uiso 1 1 d .
H5B H 0.311(5) 0.284(3) 0.316(5) 0.06(2) Uiso 1 1 d .
H8B H 0.357(4) 0.570(2) 0.416(4) 0.036(13) Uiso 1 1 d .
H9C H 0.431(7) -0.066(4) 0.124(7) 0.13(3) Uiso 1 1 d .
H3A H 0.175(4) 0.117(2) 0.422(4) 0.033(13) Uiso 1 1 d .
H1A H -0.080(10) 0.415(5) 0.370(11) 0.23(6) Uiso 1 1 d .
H4A H -0.209(8) 0.169(4) 0.403(7) 0.14(4) Uiso 1 1 d .
H7B H 0.340(5) 0.513(3) 0.032(5) 0.058(19) Uiso 1 1 d .
H11C H 0.340(5) 0.231(3) 0.128(5) 0.06(2) 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
C6 C5 C4 119.8(4)
C3 C2 C7 121.4(4)
C3 C2 C1 119.6(4)
C7 C2 C1 118.9(4)
C2 C3 C4 118.7(4)
C6 C7 C2 118.0(4)
O2 C1 O1 124.6(4)
O2 C1 C2 118.1(4)
O1 C1 C2 117.3(4)
O3 C4 C5 120.7(4)
O3 C4 C3 118.5(4)
C5 C4 C3 120.8(4)
O4 C6 C5 116.1(4)
O4 C6 C7 122.6(4)
C5 C6 C7 121.3(4)
C20 C19 C18 118.9(4)
C17 C16 C21 120.3(4)
C17 C16 C15 120.7(4)
C21 C16 C15 118.9(4)
C20 C21 C16 118.8(4)
C18 C17 C16 119.4(4)
O11 C18 C17 118.6(4)
O11 C18 C19 120.6(4)
C17 C18 C19 120.8(4)
C21 C20 O12 121.7(4)
C21 C20 C19 121.8(4)
O12 C20 C19 116.4(4)
O10 C15 O9 123.7(4)
O10 C15 C16 119.6(4)
O9 C15 C16 116.7(4)
C13 C12 C11 119.2(4)
C14 C13 O7 122.3(4)
C14 C13 C12 121.7(4)
O7 C13 C12 116.0(4)
C11 C10 C9 118.5(4)
C10 C9 C14 121.2(4)
C10 C9 C8 119.9(4)
C14 C9 C8 119.0(4)
O8 C11 C12 121.8(4)
O8 C11 C10 117.4(4)
C12 C11 C10 120.9(4)
C13 C14 C9 118.5(4)
O6 C8 O5 123.8(4)
O6 C8 C9 123.2(4)
O5 C8 C9 113.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C1 1.244(5)
O1 C1 1.269(5)
O3 C4 1.374(5)
C5 C6 1.376(6)
C5 C4 1.381(6)
O4 C6 1.374(5)
C2 C3 1.382(6)
C2 C7 1.406(6)
C2 C1 1.494(6)
C3 C4 1.387(6)
C7 C6 1.382(6)
O12 C20 1.380(5)
O10 C15 1.246(5)
O9 C15 1.281(5)
O11 C18 1.370(5)
C19 C20 1.381(6)
C19 C18 1.385(6)
C16 C17 1.394(6)
C16 C21 1.396(6)
C16 C15 1.478(6)
C21 C20 1.373(6)
C17 C18 1.379(6)
O7 C13 1.374(5)
C12 C13 1.374(6)
C12 C11 1.380(6)
O5 C8 1.317(6)
O8 C11 1.371(5)
O6 C8 1.204(6)
C13 C14 1.371(6)
C10 C11 1.385(6)
C10 C9 1.388(6)
C9 C14 1.388(6)
C9 C8 1.491(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144730
