#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:49:30 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179598 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/62/4506224.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_4506224
loop_
_publ_author_name
'André, Vânia'
'Duarte, M. Teresa'
'Braga, Dario'
'Grepioni, Fabrizia'
_publ_section_title
;
 Polymorphic Ammonium Salts of the Antibiotic 4-Aminosalicylic Acid
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3082
_journal_paper_doi               10.1021/cg300284z
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         C7H6N1O3N1H4
_chemical_formula_sum            'C7 H10 N2 O3'
_chemical_formula_weight         170.17
_chemical_name_common            4ASA_NH4_III
_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                 94.972(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.736(3)
_cell_length_b                   3.7600(10)
_cell_length_c                   29.484(8)
_cell_measurement_reflns_used    1636
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      4.01
_cell_volume                     964.8(5)
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_collection       'BRUKER APEX2 (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.1568
_diffrn_reflns_av_sigmaI/netI    0.1568
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            7094
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         4.01
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.09(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1636
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.3533
_refine_ls_R_factor_gt           0.1805
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4067
_refine_ls_wR_factor_ref         0.4694
_reflns_number_gt                511
_reflns_number_total             1636
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg300284z_si_003.cif
_cod_data_source_block           ASANH4III
_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_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4506224
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
O1 O 0.5123(10) 0.005(3) 0.0676(2) 0.117(3) Uani 1 1 d .
H1 H 0.5526 -0.0175 0.0437 0.176 Uiso 1 1 calc R
O2 O 0.7279(11) -0.0525(18) 0.0173(2) 0.096(3) Uani 1 1 d .
O3 O 0.9748(13) 0.075(3) 0.0398(2) 0.105(4) Uani 1 1 d .
N1 N 0.6331(8) 0.436(2) 0.2176(2) 0.073(3) Uani 1 1 d .
H12 H 0.6980 0.5230 0.2383 0.088 Uiso 1 1 calc R
H11 H 0.5381 0.4138 0.2227 0.088 Uiso 1 1 calc R
C1 C 0.7776(17) 0.153(2) 0.0923(3) 0.082(4) Uani 1 1 d .
C2 C 0.6170(14) 0.144(3) 0.1003(3) 0.066(3) Uani 1 1 d .
C3 C 0.5812(14) 0.196(3) 0.1401(4) 0.089(4) Uani 1 1 d .
H3 H 0.4811 0.1382 0.1458 0.107 Uiso 1 1 calc R
C4 C 0.6791(18) 0.338(3) 0.1780(3) 0.083(4) Uani 1 1 d .
C5 C 0.8352(15) 0.372(2) 0.1687(3) 0.068(3) Uani 1 1 d .
H5 H 0.9079 0.4623 0.1906 0.081 Uiso 1 1 calc R
C6 C 0.8777(14) 0.267(3) 0.1263(3) 0.082(4) Uani 1 1 d .
H6 H 0.9812 0.2772 0.1212 0.099 Uiso 1 1 calc R
C7 C 0.835(3) 0.044(3) 0.0476(3) 0.104(5) Uani 1 1 d .
N2 N 0.2351(14) 0.537(5) 0.0614(6) 0.132(5) Uani 1 1 d D
H16 H 0.174(14) 0.45(3) 0.082(4) 0.19(10) Uiso 1 1 d D
H13 H 0.219(15) 0.773(9) 0.060(5) 0.12(6) Uiso 1 1 d D
H15 H 0.23(2) 0.47(10) 0.032(4) 0.34(17) Uiso 1 1 d D
H14 H 0.333(6) 0.50(5) 0.073(5) 0.21(9) Uiso 1 1 d 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
O1 0.125(7) 0.152(8) 0.065(5) -0.023(5) -0.041(5) -0.012(6)
O2 0.177(8) 0.062(5) 0.048(4) -0.004(3) 0.007(5) -0.010(5)
O3 0.147(8) 0.134(8) 0.038(4) -0.035(4) 0.027(5) -0.017(7)
N1 0.059(5) 0.107(7) 0.056(5) 0.000(4) 0.018(4) -0.001(5)
C1 0.144(11) 0.048(6) 0.046(6) -0.004(4) -0.042(7) -0.016(6)
C2 0.099(9) 0.069(7) 0.031(5) 0.001(4) 0.019(5) 0.000(6)
C3 0.098(9) 0.098(9) 0.071(8) -0.017(6) 0.003(7) 0.015(6)
C4 0.162(13) 0.074(7) 0.010(4) 0.010(4) -0.009(6) 0.021(8)
C5 0.118(10) 0.041(5) 0.043(5) -0.014(4) 0.003(6) -0.008(6)
C6 0.128(10) 0.080(7) 0.039(5) -0.002(5) 0.004(6) -0.002(6)
C7 0.216(17) 0.072(8) 0.021(6) 0.016(5) -0.016(8) 0.023(10)
N2 0.060(7) 0.162(15) 0.171(13) -0.077(11) -0.001(8) 0.030(8)
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 117.7(11)
C6 C1 C7 119.6(15)
C2 C1 C7 122.8(11)
C3 C2 O1 120.7(11)
C3 C2 C1 118.3(11)
O1 C2 C1 119.5(8)
C2 C3 C4 126.9(13)
N1 C4 C5 121.2(10)
N1 C4 C3 125.5(14)
C5 C4 C3 113.3(9)
C6 C5 C4 119.0(10)
C1 C6 C5 123.7(13)
O3 C7 O2 123.7(12)
O3 C7 C1 122.4(13)
O2 C7 C1 113.7(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.373(12)
O2 C7 1.291(16)
O3 C7 1.264(18)
N1 C4 1.320(12)
C1 C6 1.343(13)
C1 C2 1.443(15)
C1 C7 1.507(19)
C2 C3 1.256(13)
C3 C4 1.449(15)
C4 C5 1.421(15)
C5 C6 1.391(13)
