#------------------------------------------------------------------------------
#$Date: 2008-03-30 13:21:05 +0300 (Sun, 30 Mar 2008) $
#$Revision: 321 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2100548.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_2100548
loop_
_publ_author_name
'Munshi, Parthapratim'
'Guru Row, T. N.'
_publ_section_title
;
Intra- and intermolecular interactions in small bioactive molecules:
cooperative features from experimental and theoretical charge-density
analysis
;
_journal_coeditor_code           LC5044
_journal_issue                   4
_journal_name_full               'Acta Crystallographica, Section B'
_journal_page_first              612
_journal_page_last               626
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C7 H6 O3'
_chemical_formula_sum            'C7 H6 O3'
_chemical_formula_weight         138.12
_chemical_name_common            'Salicylic acid'
_chemical_name_systematic
;
2-hydroxybenzoic acid
;
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_atom_sites_solution_hydrogens   ' geom   '
_atom_sites_solution_primary     ' direct '
_atom_sites_solution_secondary   ' difmap '
_cell_angle_alpha                90
_cell_angle_beta                 92.621(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8818(2)
_cell_length_b                   11.2009(5)
_cell_length_c                   11.2335(5)
_cell_measurement_reflns_used    31354
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      50.3
_cell_measurement_theta_min      2.57
_cell_volume                     613.61(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'
_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\f & \w 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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31354
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        50.30
_diffrn_reflns_theta_max         50.30
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9767
_exptl_absorpt_correction_T_min  0.8861
_exptl_absorpt_correction_type   ' multi-scan '
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            ' colorless '
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       ' prism '
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     ' none '
_refine_ls_goodness_of_fit_ref   1.9642
_refine_ls_hydrogen_treatment    'noref '
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         5439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0200
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
     calc w2 = q/[s^2^(Fo^2^) + (0.00 P)^2^ + 0.00 P + 0.00 + 0.00 sin(th)]
     where P = (0.3333 Fo^2^ + 0.6667 Fc^2^)
           q = 1.0
;
_refine_ls_weighting_scheme      ' calc  '
_refine_ls_wR_factor_ref         0.0204
_reflns_number_gt                5439
_reflns_number_total             6440
_reflns_threshold_expression     >3sigma(I)
_[local]_cod_data_source_file    lc5044.cif
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
O(1) 0.83999(4) 0.13928(2) -0.05215(2) 0.014 1.0000
O(3) 0.39275(5) 0.06756(2) 0.24999(2) 0.016 1.0000
O(2) 0.76762(4) 0.01483(2) 0.09897(2) 0.013 1.0000
C(1) 0.50516(3) 0.19284(2) 0.08238(2) 0.010 1.0000
C(3) 0.15873(4) 0.24924(2) 0.22021(2) 0.014 1.0000
C(6) 0.45370(4) 0.29928(2) 0.01908(2) 0.013 1.0000
C(2) 0.35609(4) 0.16777(2) 0.18410(2) 0.012 1.0000
C(5) 0.25886(4) 0.37961(2) 0.05541(2) 0.015 1.0000
C(4) 0.11104(4) 0.35399(2) 0.15648(2) 0.015 1.0000
C(7) 0.71398(3) 0.10908(2) 0.04397(2) 0.010 1.0000
H(6) 0.57311 0.31697 -0.05713 0.027(2) 1.0000
H(3) 0.04064 0.22880 0.29617 0.030(2) 1.0000
H(5) 0.21541 0.45737 0.00156 0.036(2) 1.0000
H(4) -0.04312 0.41534 0.18430 0.036(2) 1.0000
H(2) 0.54071 0.02176 0.21898 0.017(2) 1.0000
H(1) 0.98372 0.07598 -0.07049 0.013(2) 1.0000
DUM0 0.00000 0.00000 0.00000 0.000 0.0000
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
O(1) 0.01430(7) 0.01378(6) 0.01421(6) 0.00347(6) 0.00571(5) 0.00264(6)
O(3) 0.01832(8) 0.01545(7) 0.01425(7) 0.00385(6) 0.00600(6) 0.00245(6)
O(2) 0.01341(6) 0.01152(5) 0.01396(6) 0.00309(5) 0.00397(5) 0.00218(5)
C(1) 0.00986(5) 0.01006(5) 0.01145(6) 0.00119(5) 0.00128(4) -0.00038(5)
C(3) 0.01351(7) 0.01583(7) 0.01403(6) 0.00326(6) 0.00273(5) -0.00293(6)
C(6) 0.01237(6) 0.01147(6) 0.01546(6) 0.00205(5) 0.00152(5) 0.00136(5)
C(2) 0.01145(6) 0.01200(6) 0.01141(6) 0.00152(5) 0.00202(5) -0.00112(5)
C(5) 0.01407(7) 0.01204(6) 0.01979(8) 0.00347(5) 0.00050(6) -0.00003(6)
C(4) 0.01348(7) 0.01417(7) 0.01786(7) 0.00388(6) 0.00044(6) -0.00383(6)
C(7) 0.01001(5) 0.01005(5) 0.01117(5) 0.00092(5) 0.00191(4) 0.00023(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(7) 1_555 1_555 1.3113(2) yes
O(1) H(1) 1_555 1_555 1.02500(19) yes
O(3) C(2) 1_555 1_555 1.3519(3) yes
O(3) H(2) 1_555 1_555 0.9640(2) yes
O(2) C(7) 1_555 1_555 1.2450(2) yes
C(1) C(6) 1_555 1_555 1.4049(3) yes
C(1) C(2) 1_555 1_555 1.4107(2) yes
C(1) C(7) 1_555 1_555 1.4648(2) yes
C(3) C(2) 1_555 1_555 1.4005(3) yes
C(3) C(4) 1_555 1_555 1.3886(3) yes
C(3) H(3) 1_555 1_555 1.0760(2) yes
C(6) C(5) 1_555 1_555 1.3843(3) yes
C(6) H(6) 1_555 1_555 1.0760(2) yes
C(5) C(4) 1_555 1_555 1.4025(3) yes
C(5) H(5) 1_555 1_555 1.0760(2) yes
C(4) H(4) 1_555 1_555 1.0760(2) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C(7) O(1) H(1) 1_555 1_555 1_555 109.777(18) yes
C(2) O(3) H(2) 1_555 1_555 1_555 109.061(18) yes
C(6) C(1) C(2) 1_555 1_555 1_555 119.465(16) yes
C(6) C(1) C(7) 1_555 1_555 1_555 120.344(16) yes
C(2) C(1) C(7) 1_555 1_555 1_555 120.187(16) yes
C(2) C(3) C(4) 1_555 1_555 1_555 120.166(18) yes
C(2) C(3) H(3) 1_555 1_555 1_555 119.45(2) yes
C(4) C(3) H(3) 1_555 1_555 1_555 120.356(18) yes
C(1) C(6) C(5) 1_555 1_555 1_555 120.781(18) yes
C(1) C(6) H(6) 1_555 1_555 1_555 117.917(17) yes
C(5) C(6) H(6) 1_555 1_555 1_555 121.291(18) yes
O(3) C(2) C(1) 1_555 1_555 1_555 123.262(17) yes
O(3) C(2) C(3) 1_555 1_555 1_555 117.254(18) yes
C(1) C(2) C(3) 1_555 1_555 1_555 119.484(18) yes
C(6) C(5) C(4) 1_555 1_555 1_555 119.444(19) yes
C(6) C(5) H(5) 1_555 1_555 1_555 118.74(2) yes
C(4) C(5) H(5) 1_555 1_555 1_555 121.682(19) yes
C(3) C(4) C(5) 1_555 1_555 1_555 120.659(18) yes
C(3) C(4) H(4) 1_555 1_555 1_555 119.52(2) yes
C(5) C(4) H(4) 1_555 1_555 1_555 119.81(2) yes
O(1) C(7) O(2) 1_555 1_555 1_555 122.100(17) yes
O(1) C(7) C(1) 1_555 1_555 1_555 115.871(17) yes
O(2) C(7) C(1) 1_555 1_555 1_555 122.028(16) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
H(1) O(1) C(7) O(2) 1_555 1_555 1_555 1_555 -1.30(10) yes
H(1) O(1) C(7) C(1) 1_555 1_555 1_555 1_555 178.90(10) yes
H(2) O(3) C(2) C(1) 1_555 1_555 1_555 1_555 3.70(10) yes
H(2) O(3) C(2) C(3) 1_555 1_555 1_555 1_555 -176.50(10) yes
C(6) C(1) C(2) O(3) 1_555 1_555 1_555 1_555 180.00(10) yes
C(6) C(1) C(2) C(3) 1_555 1_555 1_555 1_555 0.10(10) yes
C(2) C(1) C(6) C(5) 1_555 1_555 1_555 1_555 0.00(10) yes
C(2) C(1) C(6) H(6) 1_555 1_555 1_555 1_555 178.80(10) yes
C(6) C(1) C(7) O(1) 1_555 1_555 1_555 1_555 -1.30(10) yes
C(6) C(1) C(7) O(2) 1_555 1_555 1_555 1_555 178.90(10) yes
C(7) C(1) C(6) C(5) 1_555 1_555 1_555 1_555 -179.30(10) yes
C(7) C(1) C(6) H(6) 1_555 1_555 1_555 1_555 -0.50(10) yes
C(2) C(1) C(7) O(1) 1_555 1_555 1_555 1_555 179.30(10) yes
C(7) C(1) C(2) O(3) 1_555 1_555 1_555 1_555 -0.70(10) yes
C(2) C(1) C(7) O(2) 1_555 1_555 1_555 1_555 -0.40(10) yes
C(7) C(1) C(2) C(3) 1_555 1_555 1_555 1_555 179.50(10) yes
C(4) C(3) C(2) O(3) 1_555 1_555 1_555 1_555 180.00(10) yes
C(4) C(3) C(2) C(1) 1_555 1_555 1_555 1_555 -0.20(10) yes
C(2) C(3) C(4) C(5) 1_555 1_555 1_555 1_555 0.10(10) yes
C(2) C(3) C(4) H(4) 1_555 1_555 1_555 1_555 179.10(10) yes
H(3) C(3) C(2) O(3) 1_555 1_555 1_555 1_555 -1.80(10) yes
H(3) C(3) C(2) C(1) 1_555 1_555 1_555 1_555 178.10(10) yes
H(3) C(3) C(4) C(5) 1_555 1_555 1_555 1_555 -178.20(10) yes
H(3) C(3) C(4) H(4) 1_555 1_555 1_555 1_555 0.90(10) yes
C(1) C(6) C(5) C(4) 1_555 1_555 1_555 1_555 -0.20(10) yes
C(1) C(6) C(5) H(5) 1_555 1_555 1_555 1_555 -176.00(10) yes
H(6) C(6) C(5) C(4) 1_555 1_555 1_555 1_555 -178.90(10) yes
H(6) C(6) C(5) H(5) 1_555 1_555 1_555 1_555 5.20(10) yes
C(6) C(5) C(4) C(3) 1_555 1_555 1_555 1_555 0.10(10) yes
C(6) C(5) C(4) H(4) 1_555 1_555 1_555 1_555 -178.90(10) yes
H(5) C(5) C(4) C(3) 1_555 1_555 1_555 1_555 175.80(10) yes
H(5) C(5) C(4) H(4) 1_555 1_555 1_555 1_555 -3.20(10) yes