#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/27/2102782.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2102782
loop_
_publ_author_name
'Parkin, Andrew'
'Adam, Martin'
'Cooper, Richard I.'
'Middlemiss, Derek S.'
'Wilson, Chick C.'
_publ_section_title
;
 Structure and hydrogen bonding in 2,4-dihydroxybenzoic acid at 90,
 100, 110 and 150K; a theoretical and single-crystal X-ray diffraction
 study
;
_journal_coeditor_code           BS5037
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              303
_journal_page_last               308
_journal_paper_doi               10.1107/S0108768106055212
_journal_volume                  63
_journal_year                    2007
_chemical_formula_moiety         'C7 H6 O4'
_chemical_formula_sum            'C7 H6 O4'
_chemical_formula_weight         154.12
_chemical_name_systematic        '2,4-dihydroxybenzoic acid'
_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
_audit_creation_method           CRYSTALS_ver_12.24
_cell_angle_alpha                90
_cell_angle_beta                 99.630(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.6686(5)
_cell_length_b                   22.333(3)
_cell_length_c                   8.0046(11)
_cell_measurement_reflns_used    10028
_cell_measurement_temperature    90
_cell_measurement_theta_max      35
_cell_measurement_theta_min      0
_cell_volume                     646.58(15)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1996)'
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1996)'
_computing_molecular_graphics    'CAMERON (Watkin et al 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.775
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5714
_diffrn_reflns_theta_full        26.040
_diffrn_reflns_theta_max         33.818
_diffrn_reflns_theta_min         1.824
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.71
_refine_diff_density_min         -0.83
_refine_ls_extinction_coef       12(7)
_refine_ls_extinction_method
'Larson 1970 Crystallographic Computing eq 22'
_refine_ls_goodness_of_fit_ref   0.9636
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         2019
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000164
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 p=P(6)*max(Fo²,0) + (1-P(6))Fc²
 Method = SHELXL 97 (Sheldrick, 1997)
 W = 1. / [Sigma²(F*)+(P(1)p)²+P(2)p+P(4)+P(5)Sin(theta) ]
 P(i) are:
 0.322E-01 0.690 0.00 0.00 0.00 0.333
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1317
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                1301
_reflns_number_total             2022
_reflns_threshold_expression     I>2.00s(I)
_cod_data_source_file            bs5037.cif
_cod_data_source_block           90k
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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      'P 1 21/n 1 '
_cod_database_code               2102782
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_site_type_symbol
_atom_site_label
_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
C C1 0.3016(5) 0.09421(8) 0.7174(2) 0.0136 Uani 1.0000
C C2 0.3938(5) 0.15429(8) 0.7589(2) 0.0135 Uani 1.0000
O O2 0.3800(4) 0.17744(6) 0.91619(17) 0.0182 Uani 1.0000
C C3 0.5016(5) 0.19267(8) 0.6389(2) 0.0144 Uani 1.0000
C C4 0.5175(5) 0.17137(8) 0.4772(2) 0.0144 Uani 1.0000
O O4 0.6182(4) 0.20656(6) 0.35487(18) 0.0179 Uani 1.0000
C C5 0.4250(5) 0.11172(8) 0.4325(2) 0.0157 Uani 1.0000
C C6 0.3196(5) 0.07420(8) 0.5523(2) 0.0143 Uani 1.0000
C C7 0.1800(5) 0.05422(8) 0.8407(2) 0.0142 Uani 1.0000
O O8 0.1500(4) 0.07026(6) 0.98746(17) 0.0179 Uani 1.0000
O O9 0.1034(4) -0.00118(6) 0.78791(18) 0.0183 Uani 1.0000
H H31 0.5677 0.2352 0.6689 0.0170 Uiso 1.0000
H H51 0.4378 0.0967 0.3160 0.0195 Uiso 1.0000
H H61 0.2535 0.0317 0.5214 0.0179 Uiso 1.0000
H H4 0.682(9) 0.2419(15) 0.397(4) 0.052(9) Uiso 1.0000
H H81 0.0734 0.0440 1.0596 0.070(11) Uiso 0.0000
H H82 0.2057 0.1081 1.0210 0.028(9) Uiso 0.3000
H H9 0.0264 -0.0281 0.8581 0.070(11) Uiso 1.0000
H H2 0.3101 0.1540 0.9968 0.031(9) Uiso 0.7000
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0134(9) 0.0120(9) 0.0161(9) 0.0000(7) 0.0043(7) 0.0011(7)
C2 0.0131(9) 0.0143(9) 0.0133(8) 0.0011(7) 0.0030(7) -0.0005(7)
O2 0.0277(8) 0.0137(7) 0.0142(7) -0.0018(6) 0.0065(6) -0.0021(5)
C3 0.0151(9) 0.0114(9) 0.0174(9) -0.0002(6) 0.0045(7) 0.0020(7)
C4 0.0128(8) 0.0150(9) 0.0159(9) 0.0008(7) 0.0038(7) 0.0055(7)
O4 0.0245(8) 0.0150(7) 0.0156(7) -0.0011(6) 0.0078(6) 0.0022(5)
C5 0.0154(9) 0.0164(9) 0.0159(9) 0.0000(7) 0.0038(7) -0.0019(7)
C6 0.0149(9) 0.0127(9) 0.0158(9) 0.0004(7) 0.0036(7) -0.0003(7)
C7 0.0131(9) 0.0142(9) 0.0153(8) 0.0009(7) 0.0021(7) 0.0018(7)
O8 0.0253(8) 0.0143(7) 0.0148(7) -0.0026(6) 0.0052(6) 0.0001(5)
O9 0.0264(8) 0.0107(6) 0.0189(7) -0.0041(6) 0.0074(6) -0.0006(5)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 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_publ_flag
C2 C1 C6 118.48(16) yes
C2 C1 C7 120.85(16) yes
C6 C1 C7 120.64(17) yes
C1 C2 O2 122.12(16) yes
C1 C2 C3 120.51(17) yes
O2 C2 C3 117.38(17) yes
C2 O2 H2 119.895 no
C2 C3 C4 119.51(17) yes
C2 C3 H31 120.279 no
C4 C3 H31 120.209 no
C3 C4 O4 122.28(17) yes
C3 C4 C5 121.02(17) yes
O4 C4 C5 116.70(17) yes
C4 O4 H4 109(2) no
C4 C5 C6 118.91(17) yes
C4 C5 H51 120.546 no
C6 C5 H51 120.538 no
C1 C6 C5 121.57(17) yes
C1 C6 H61 119.105 no
C5 C6 H61 119.328 no
C1 C7 O8 123.12(17) yes
C1 C7 O9 115.49(16) yes
O8 C7 O9 121.39(17) yes
C7 O8 H81 120.139 no
C7 O8 H82 119.860 no
H81 O8 H82 120.000 no
C7 O9 H9 119.839 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.410(3) yes
C1 C6 1.406(3) yes
C1 C7 1.456(3) yes
C2 O2 1.370(2) yes
C2 C3 1.393(3) yes
O2 H2 0.900 no
C3 C4 1.389(3) yes
C3 H31 1.000 no
C4 O4 1.354(2) yes
C4 C5 1.406(3) yes
O4 H4 0.88(3) no
C5 C6 1.377(3) yes
C5 H51 1.000 no
C6 H61 1.000 no
C7 O8 1.251(2) yes
C7 O9 1.322(2) yes
O8 H81 0.900 no
O8 H82 0.900 no
O9 H9 0.900 no
