#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:03:52 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179611 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/75/4507573.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_4507573
loop_
_publ_author_name
'Cherukuvada, Suryanarayan'
'Bolla, Geetha'
'Sikligar, Kanishka'
'Nangia, Ashwini'
_publ_section_title
;
 4-Aminosalicylic Acid Adducts
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1551
_journal_paper_doi               10.1021/cg301798s
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C7 H7 N O3'
_chemical_formula_weight         153.14
_chemical_name_systematic
; 
 ? 
;
_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                 91.889(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.7161(4)
_cell_length_b                   7.3629(9)
_cell_length_c                   23.307(3)
_cell_measurement_reflns_used    2089
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.90
_cell_volume                     637.36(13)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6398
_diffrn_reflns_theta_full        26.07
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0589
_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)+(0.0717P)²+0.5003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1456
_reflns_number_gt                1016
_reflns_number_total             1270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301798s_si_008.cif
_cod_data_source_block           5-Aminosalicylic-acid
_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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               4507573
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
O2 O 0.6551(5) -0.3961(2) 0.11722(8) 0.0185(5) Uani 1 1 d .
O1 O 0.5854(5) -0.1950(2) 0.20565(8) 0.0200(5) Uani 1 1 d .
O3 O 0.4452(5) -0.3074(2) 0.03156(7) 0.0172(5) Uani 1 1 d .
C1 C 0.4114(6) -0.0995(3) 0.10967(10) 0.0137(6) Uani 1 1 d .
C2 C 0.2758(6) 0.0398(3) 0.07449(10) 0.0137(5) Uani 1 1 d .
H2 H 0.2481 0.0210 0.0343 0.016 Uiso 1 1 calc R
C3 C 0.2152(6) 0.2340(3) 0.15654(11) 0.0162(6) Uani 1 1 d .
H3 H 0.1450 0.3471 0.1723 0.019 Uiso 1 1 calc R
C4 C 0.1821(6) 0.2040(3) 0.09781(10) 0.0135(5) Uani 1 1 d .
N1 N 0.0433(6) 0.3501(3) 0.06020(9) 0.0146(5) Uani 1 1 d .
C5 C 0.4531(6) -0.0686(3) 0.16875(11) 0.0148(6) Uani 1 1 d .
C6 C 0.5094(6) -0.2786(3) 0.08378(10) 0.0133(5) Uani 1 1 d .
C7 C 0.3508(7) 0.0982(3) 0.19188(11) 0.0169(6) Uani 1 1 d .
H7 H 0.3749 0.1181 0.2321 0.020 Uiso 1 1 calc R
H1 H 0.637(9) -0.300(5) 0.1793(15) 0.044(9) Uiso 1 1 d .
H5 H -0.102(7) 0.303(4) 0.0278(12) 0.018(7) Uiso 1 1 d .
H4 H 0.231(10) 0.412(5) 0.0426(14) 0.040(9) Uiso 1 1 d .
H6 H -0.103(10) 0.437(5) 0.0830(16) 0.057(11) Uiso 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
O2 0.0264(10) 0.0069(9) 0.0223(10) 0.0025(7) 0.0022(7) 0.0058(7)
O1 0.0295(11) 0.0125(9) 0.0179(10) 0.0033(8) -0.0007(8) 0.0048(7)
O3 0.0231(9) 0.0083(9) 0.0201(10) -0.0031(7) 0.0004(7) 0.0021(7)
C1 0.0107(12) 0.0093(12) 0.0211(13) 0.0000(10) 0.0027(10) -0.0010(9)
C2 0.0163(12) 0.0094(12) 0.0152(12) 0.0006(10) -0.0001(9) -0.0009(9)
C3 0.0175(13) 0.0078(12) 0.0236(14) -0.0025(10) 0.0029(10) 0.0011(9)
C4 0.0115(12) 0.0095(12) 0.0196(13) 0.0025(10) 0.0004(9) 0.0009(9)
N1 0.0184(11) 0.0057(10) 0.0195(12) 0.0026(9) -0.0006(9) 0.0027(8)
C5 0.0150(13) 0.0097(11) 0.0197(13) 0.0020(10) 0.0009(10) -0.0003(9)
C6 0.0137(12) 0.0081(12) 0.0181(13) 0.0012(10) 0.0020(9) -0.0010(9)
C7 0.0220(14) 0.0124(12) 0.0164(13) -0.0012(10) 0.0006(10) -0.0003(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 0.0000 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
C5 O1 H1 102.2(19)
C2 C1 C5 119.0(2)
C2 C1 C6 119.8(2)
C5 C1 C6 121.2(2)
C4 C2 C1 120.3(2)
C4 C2 H2 119.8
C1 C2 H2 119.8
C7 C3 C4 119.5(2)
C7 C3 H3 120.3
C4 C3 H3 120.3
C2 C4 C3 121.0(2)
C2 C4 N1 119.7(2)
C3 C4 N1 119.3(2)
C4 N1 H5 112.2(16)
C4 N1 H4 111(2)
H5 N1 H4 103(3)
C4 N1 H6 110(2)
H5 N1 H6 110(3)
H4 N1 H6 111(3)
O1 C5 C7 117.2(2)
O1 C5 C1 122.8(2)
C7 C5 C1 119.9(2)
O3 C6 O2 123.0(2)
O3 C6 C1 119.9(2)
O2 C6 C1 117.1(2)
C3 C7 C5 120.3(2)
C3 C7 H7 119.8
C5 C7 H7 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C6 1.273(3)
O1 C5 1.349(3)
O1 H1 1.01(4)
O3 C6 1.251(3)
C1 C2 1.396(3)
C1 C5 1.399(3)
C1 C6 1.500(3)
C2 C4 1.375(3)
C2 H2 0.9500
C3 C7 1.380(3)
C3 C4 1.388(3)
C3 H3 0.9500
C4 N1 1.471(3)
N1 H5 0.97(3)
N1 H4 0.94(4)
N1 H6 1.00(4)
C5 C7 1.399(3)
C7 H7 0.9500
