#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:08:36 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180413 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/82/7208262.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_7208262
loop_
_publ_author_name
'Montis, Riccardo'
'Hursthouse, Michael B.'
_publ_section_title
;
 Surprisingly complex supramolecular behaviour in the crystal structures
 of a family of mono-substituted salicylic acids
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              5242
_journal_paper_doi               10.1039/c2ce25336d
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C7 H7 N O3'
_chemical_formula_sum            'C7 H7 N O3'
_chemical_formula_weight         153.14
_chemical_name_common            5-aminosalicylic_acid
_chemical_name_systematic
;
5-amino-2-hydroxobenzoic acid monohydrate
;
_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                 91.806(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.7239(2)
_cell_length_b                   7.3696(4)
_cell_length_c                   23.3107(11)
_cell_measurement_reflns_used    4776
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     639.41(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on -goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5940
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0682P)²+0.1137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                1077
_reflns_number_total             1460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25336d.txt
_cod_data_source_block           5-aminosalicylic_acid
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7208262
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
_atom_site_refinement_flags
H1B H -0.088(5) 0.191(3) 0.0288(8) 0.022(5) Uiso 1 1 d .
H1A H 0.223(6) 0.085(3) 0.0443(9) 0.030(5) Uiso 1 1 d .
H1C H -0.093(5) 0.063(3) 0.0835(8) 0.028(5) Uiso 1 1 d .
H3A H 0.646(6) 0.795(3) 0.1816(10) 0.049(7) Uiso 1 1 d .
C1 C 0.4114(4) 0.5996(2) 0.10969(7) 0.0131(4) Uani 1 1 d .
C2 C 0.4527(4) 0.5679(2) 0.16886(7) 0.0145(4) Uani 1 1 d .
C3 C 0.3500(4) 0.4009(2) 0.19177(7) 0.0183(4) Uani 1 1 d .
H3 H 0.3735 0.3806 0.2320 0.022 Uiso 1 1 calc R
C4 C 0.2152(4) 0.2659(2) 0.15642(7) 0.0161(4) Uani 1 1 d .
H4 H 0.1450 0.1529 0.1721 0.019 Uiso 1 1 calc R
C5 C 0.1823(4) 0.2957(2) 0.09784(7) 0.0145(4) Uani 1 1 d .
C6 C 0.2755(4) 0.4602(2) 0.07428(7) 0.0128(4) Uani 1 1 d .
H6 H 0.2475 0.4791 0.0341 0.015 Uiso 1 1 calc R
C7 C 0.5091(4) 0.7781(2) 0.08393(7) 0.0146(4) Uani 1 1 d .
N1 N 0.0426(4) 0.15014(19) 0.06028(7) 0.0160(4) Uani 1 1 d .
O1 O 0.6545(3) 0.89630(15) 0.11729(5) 0.0205(3) Uani 1 1 d .
O2 O 0.4443(3) 0.80733(15) 0.03151(5) 0.0192(3) Uani 1 1 d .
O3 O 0.5854(3) 0.69506(16) 0.20563(5) 0.0213(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0099(8) 0.0124(8) 0.0170(9) -0.0013(7) 0.0017(6) 0.0008(6)
C2 0.0127(9) 0.0152(8) 0.0156(8) -0.0039(7) -0.0002(6) -0.0010(6)
C3 0.0211(9) 0.0196(9) 0.0143(9) 0.0018(7) 0.0014(7) -0.0013(7)
C4 0.0156(9) 0.0131(8) 0.0197(9) 0.0028(7) 0.0022(6) -0.0015(6)
C5 0.0109(8) 0.0133(8) 0.0191(9) -0.0020(7) -0.0002(6) -0.0001(6)
C6 0.0118(8) 0.0127(8) 0.0140(8) 0.0005(7) 0.0023(6) 0.0007(6)
C7 0.0118(8) 0.0138(8) 0.0182(9) -0.0010(7) 0.0014(6) 0.0019(6)
N1 0.0171(8) 0.0129(7) 0.0179(8) -0.0008(6) 0.0012(6) -0.0023(6)
O1 0.0262(7) 0.0137(6) 0.0214(7) -0.0011(5) -0.0005(5) -0.0059(5)
O2 0.0225(7) 0.0165(6) 0.0185(6) 0.0031(5) -0.0007(5) -0.0022(5)
O3 0.0285(7) 0.0186(7) 0.0168(7) -0.0027(6) -0.0002(5) -0.0067(5)
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'
N N 0.0061 0.0033 '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 C1 C2 118.91(14)
C6 C1 C7 119.72(14)
C2 C1 C7 121.37(14)
O3 C2 C3 117.78(14)
O3 C2 C1 122.30(14)
C3 C2 C1 119.92(15)
C4 C3 C2 120.40(15)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 119.68(15)
C3 C4 H4 120.2
C5 C4 H4 120.2
C6 C5 C4 121.07(15)
C6 C5 N1 119.54(14)
C4 C5 N1 119.38(14)
C5 C6 C1 120.00(15)
C5 C6 H6 120.0
C1 C6 H6 120.0
O2 C7 O1 122.69(15)
O2 C7 C1 119.96(14)
O1 C7 C1 117.35(14)
C5 N1 H1B 113.9(12)
C5 N1 H1A 112.0(13)
H1B N1 H1A 102.9(18)
C5 N1 H1C 108.9(11)
H1B N1 H1C 112.7(16)
H1A N1 H1C 106.1(17)
C2 O3 H3A 104.5(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.402(2)
C1 C2 1.402(2)
C1 C7 1.496(2)
C2 O3 1.3530(19)
C2 C3 1.400(2)
C3 C4 1.377(2)
C3 H3 0.9500
C4 C5 1.384(2)
C4 H4 0.9500
C5 C6 1.380(2)
C5 N1 1.469(2)
C6 H6 0.9500
C7 O2 1.257(2)
C7 O1 1.277(2)
N1 H1B 0.92(2)
N1 H1A 0.92(2)
N1 H1C 0.99(2)
O3 H3A 0.96(2)
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
N1 H1A O2 0.92(2) 2.23(2) 3.0223(19) 144.6(17) 1_545
N1 H1A O2 0.92(2) 2.33(2) 2.9301(19) 123.0(16) 3_665
O3 H3A O1 0.96(2) 1.68(2) 2.5572(17) 152(2) .
