#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:35:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180086 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/32/7053272.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_7053272
loop_
_publ_author_name
'Adam, Martin S.'
'Gutmann, Matthias J.'
'Leech, Charlotte K.'
'Middlemiss, Derek S.'
'Parkin, Andrew'
'Thomas, Lynne H.'
'Wilson, Chick C.'
_publ_section_title
;
 Stability and cooperativity of hydrogen bonds in dihydroxybenzoic acids
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              85
_journal_paper_doi               10.1039/b9nj00353c
_journal_volume                  34
_journal_year                    2010
_chemical_formula_sum            'C7 H6 O4'
_chemical_formula_weight         154.12
_chemical_name_common            '2,5-dihydroxybenzoic acid'
_chemical_name_systematic
;
2,5-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
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.480(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6218(4)
_cell_length_b                   4.9063(3)
_cell_length_c                   23.5260(13)
_cell_measurement_temperature    300(2)
_cell_volume                     648.29(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'Nonius (1997-2001). COLLECT.'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP (Farrugia, 1997), Mercury (McRae, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.1416
_diffrn_reflns_av_unetI/netI     0.0954
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_theta_full        30.08
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.26
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.034(11)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.165
_refine_ls_R_factor_gt           0.0712
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0932P)²+0.1768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2148
_reflns_number_gt                866
_reflns_number_total             1848
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b9nj00353c.txt
_cod_data_source_block           25dhoba300k
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               7053272
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
C1 0.0854(5) 0.5222(6) 0.10460(11) 0.0335(7) Uani d 1 C
C2 0.2859(6) 0.3579(6) 0.10127(12) 0.0388(8) Uani d 1 C
C3 0.3348(6) 0.1628(7) 0.14331(13) 0.0441(8) Uani d 1 C
C4 0.1896(6) 0.1355(7) 0.18743(12) 0.0398(8) Uani d 1 C
C5 -0.0117(5) 0.2993(6) 0.19148(11) 0.0331(7) Uani d 1 C
C6 -0.0648(5) 0.4921(6) 0.15020(12) 0.0342(7) Uani d 1 C
C7 0.0346(6) 0.7283(6) 0.06035(12) 0.0380(8) Uani d 1 C
O9 -0.1594(4) 0.8740(5) 0.06619(9) 0.0474(7) Uani d 1 O
O8 0.1658(4) 0.7622(5) 0.02075(9) 0.0533(7) Uani d 1 O
O2 0.4396(4) 0.3753(6) 0.05839(11) 0.0601(8) Uani d 1 O
O5 -0.1506(4) 0.2620(5) 0.23792(9) 0.0452(7) Uani d 1 O
H3 0.484(8) 0.044(10) 0.1372(17) 0.093(14) Uiso d 1 H
H4 0.233(6) -0.006(9) 0.2143(15) 0.061(10) Uiso d 1 H
H6 -0.208(6) 0.614(8) 0.1487(14) 0.053(10) Uiso d 1 H
H1 -0.163(8) 0.998(12) 0.030(2) 0.122(17) Uiso d 1 H
H5 -0.216(6) 0.408(8) 0.2440(15) 0.053(12) Uiso d 1 H
H2 0.390(7) 0.506(9) 0.0377(17) 0.065(13) Uiso d 1 H
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 0.0423(17) 0.0318(15) 0.0269(14) -0.0022(13) 0.0066(11) 0.0002(11)
C2 0.0441(17) 0.0411(18) 0.0318(15) -0.0016(15) 0.0094(12) -0.0018(13)
C3 0.0422(19) 0.0446(19) 0.0454(19) 0.0066(15) 0.0026(14) 0.0015(15)
C4 0.0474(19) 0.0377(18) 0.0339(16) 0.0031(15) -0.0034(13) 0.0035(13)
C5 0.0393(17) 0.0337(16) 0.0268(14) -0.0060(13) 0.0057(11) -0.0011(12)
C6 0.0403(18) 0.0328(16) 0.0297(14) 0.0014(13) 0.0049(12) 0.0014(12)
C7 0.048(2) 0.0370(17) 0.0292(15) -0.0039(15) 0.0072(13) 0.0025(12)
O9 0.0547(14) 0.0472(14) 0.0412(12) 0.0091(11) 0.0117(10) 0.0137(11)
O8 0.0678(17) 0.0545(15) 0.0393(13) 0.0077(12) 0.0225(11) 0.0154(10)
O2 0.0577(16) 0.0715(19) 0.0534(16) 0.0129(14) 0.0295(12) 0.0140(14)
O5 0.0630(16) 0.0393(14) 0.0346(12) 0.0034(12) 0.0187(10) 0.0074(10)
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C2 C1 C6 119.9(3)
C2 C1 C7 119.5(2)
C6 C1 C7 120.6(3)
O2 C2 C1 123.2(3)
O2 C2 C3 117.2(3)
C1 C2 C3 119.6(3)
C4 C3 C2 120.3(3)
C4 C3 H3 125(2)
C2 C3 H3 115(2)
C3 C4 C5 120.9(3)
C3 C4 H4 115.4(19)
C5 C4 H4 123.7(19)
C6 C5 O5 122.3(3)
C6 C5 C4 119.9(3)
O5 C5 C4 117.7(3)
C5 C6 C1 119.5(3)
C5 C6 H6 125.7(19)
C1 C6 H6 114.8(19)
O8 C7 O9 122.3(3)
O8 C7 C1 121.8(3)
O9 C7 C1 115.8(2)
C7 O9 H1 102(3)
C2 O2 H2 106(3)
C5 O5 H5 107(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.391(4)
C1 C6 1.401(4)
C1 C7 1.470(4)
C2 O2 1.359(4)
C2 C3 1.395(4)
C3 C4 1.355(4)
C3 H3 1.04(5)
C4 C5 1.395(4)
C4 H4 0.96(4)
C5 C6 1.379(4)
C5 O5 1.382(3)
C6 H6 1.00(4)
C7 O8 1.224(3)
C7 O9 1.316(4)
O9 H1 1.05(5)
O2 H2 0.84(4)
O5 H5 0.82(4)
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
C6 C1 C2 O2 -180.0(3)
C7 C1 C2 O2 -0.6(5)
C6 C1 C2 C3 0.4(4)
C7 C1 C2 C3 179.8(3)
O2 C2 C3 C4 179.6(3)
C1 C2 C3 C4 -0.7(5)
C2 C3 C4 C5 0.5(5)
C3 C4 C5 C6 0.0(5)
C3 C4 C5 O5 -179.4(3)
O5 C5 C6 C1 179.1(3)
C4 C5 C6 C1 -0.3(4)
C2 C1 C6 C5 0.1(4)
C7 C1 C6 C5 -179.3(3)
C2 C1 C7 O8 -0.9(5)
C6 C1 C7 O8 178.5(3)
C2 C1 C7 O9 179.4(3)
C6 C1 C7 O9 -1.2(4)
