#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230318.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_2230318
loop_
_publ_author_name
'Brancatelli, Giovanna'
'Bruno, Giuseppe'
'Nicoló, Francesco'
'Canfora, Loredana'
'Ruisi, Giuseppe'
_publ_section_title
;
 (S)-2-[(2-Hydroxybenzyl)azaniumyl]-4-(methylsulfanyl)butanoate
;
_journal_coeditor_code           FY2002
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1366
_journal_page_last               o1367
_journal_paper_doi               10.1107/S1600536811016564
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H17 N O3 S'
_chemical_formula_moiety         'C12 H17 N O3 S'
_chemical_formula_sum            'C12 H17 N O3 S'
_chemical_formula_weight         255.33
_chemical_name_systematic
;
(S)-2-[(2-Hydroxybenzyl)azaniumyl]-4-(methylsulfanyl)butanoate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.200(3)
_cell_angle_beta                 90.780(3)
_cell_angle_gamma                96.849(3)
_cell_formula_units_Z            1
_cell_length_a                   5.3221(2)
_cell_length_b                   5.8369(2)
_cell_length_c                   10.5564(5)
_cell_measurement_reflns_used    4292
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      3.55
_cell_volume                     322.10(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7430
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         3.8
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prysmatic
_exptl_crystal_F_000             136
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.412
_refine_ls_abs_structure_details
;
Assigned from the known absolute structure of the starting material;
the Flack (1983) parameter is consistent with this assignment,
1119 Friedel-pairs
;
_refine_ls_abs_structure_Flack   0.12(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2324
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.059
_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)+(0.1065P)²+0.1553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.179
_reflns_number_gt                1966
_reflns_number_total             2324
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fy2002.cif
_cod_data_source_block           I
_cod_database_code               2230318
_cod_database_fobs_code          2230318
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_type_symbol
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1397(7) 0.8261(5) 0.6478(4) 0.0378(8) Uani d . 1 . .
C C2 0.1286(8) 1.0229(6) 0.7378(4) 0.0480(10) Uani d . 1 . .
H H2 0.0037 1.1192 0.7301 0.058 Uiso calc R 1 . .
C C3 0.3045(9) 1.0752(9) 0.8391(4) 0.0595(11) Uani d . 1 . .
H H3 0.2993 1.2085 0.8984 0.071 Uiso calc R 1 . .
C C4 0.4846(11) 0.9326(10) 0.8521(5) 0.0719(14) Uani d . 1 . .
H H4 0.6064 0.9719 0.918 0.086 Uiso calc R 1 . .
C C5 0.4866(8) 0.7305(8) 0.7677(5) 0.0592(11) Uani d . 1 . .
H H5 0.6034 0.6289 0.7807 0.071 Uiso calc R 1 . .
C C6 0.3176(7) 0.6750(6) 0.6635(4) 0.0437(9) Uani d . 1 . .
C C7 0.3226(7) 0.4586(6) 0.5712(5) 0.0523(11) Uani d . 1 . .
H H7A 0.1526 0.4057 0.5364 0.063 Uiso calc R 1 . .
H H7B 0.3754 0.3381 0.6164 0.063 Uiso calc R 1 . .
N N1 0.4971(5) 0.4903(4) 0.4628(3) 0.0365(7) Uani d . 1 . .
H H1A 0.4664 0.6175 0.4288 0.044 Uiso calc R 1 . .
H H1B 0.6586 0.5129 0.4927 0.044 Uiso calc R 1 . .
C C12 0.982(2) 0.7692(13) 0.1065(9) 0.125(3) Uani d . 1 . .
H H12A 0.8321 0.8384 0.0902 0.187 Uiso calc R 1 . .
H H12B 1.1162 0.8272 0.0553 0.187 Uiso calc R 1 . .
H H12C 1.0313 0.8083 0.1955 0.187 Uiso calc R 1 . .
C C8 0.4605(9) 0.2821(6) 0.3620(4) 0.0528(11) Uani d . 1 . .
H H8 0.2775 0.234 0.3533 0.063 Uiso calc R 1 . .
C C9 0.5770(7) 0.0784(5) 0.4082(4) 0.0396(8) Uani d . 1 . .
O O1 -0.0230(5) 0.7724(4) 0.5440(3) 0.0481(7) Uani d . 1 . .
H H1 -0.0734 0.8918 0.5264 0.072 Uiso calc R 1 . .
O O2 0.7473(5) 0.1274(4) 0.4933(3) 0.0542(8) Uani d . 1 . .
O O3 0.4885(6) -0.1164(4) 0.3543(3) 0.0543(8) Uani d . 1 . .
S S1 0.9203(4) 0.4659(3) 0.0671(2) 0.1140(8) Uani d . 1 . .
C C10 0.5426(11) 0.3361(8) 0.2347(5) 0.0673(14) Uani d . 1 . .
H H10A 0.4849 0.2056 0.1691 0.081 Uiso calc R 1 . .
H H10B 0.4698 0.472 0.2149 0.081 Uiso calc R 1 . .
C C11 0.8008(11) 0.3782(9) 0.2368(6) 0.0749(15) Uani d . 1 . .
H H11A 0.8727 0.24 0.2535 0.09 Uiso calc R 1 . .
H H11B 0.8581 0.5041 0.3051 0.09 Uiso calc R 1 . .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 121.9(3) ?
O1 C1 C6 . . 118.1(3) ?
C2 C1 C6 . . 120.0(3) ?
C3 C2 C1 . . 119.7(4) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C4 C3 C2 . . 120.3(4) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 120.0(5) ?
C3 C4 H4 . . 120 ?
C5 C4 H4 . . 120 ?
C4 C5 C6 . . 121.2(4) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C5 C6 C1 . . 118.4(4) ?
C5 C6 C7 . . 121.2(4) ?
C1 C6 C7 . . 120.4(4) ?
C6 C7 N1 . . 113.2(3) ?
C6 C7 H7A . . 108.9 ?
N1 C7 H7A . . 108.9 ?
C6 C7 H7B . . 108.9 ?
N1 C7 H7B . . 108.9 ?
H7A C7 H7B . . 107.8 ?
C8 N1 C7 . . 110.7(3) ?
C8 N1 H1A . . 109.5 ?
C7 N1 H1A . . 109.5 ?
C8 N1 H1B . . 109.5 ?
C7 N1 H1B . . 109.5 ?
H1A N1 H1B . . 108.1 ?
S1 C12 H12A . . 109.5 ?
S1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
S1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C10 C8 N1 . . 112.6(3) ?
C10 C8 C9 . . 115.0(4) ?
N1 C8 C9 . . 109.9(3) ?
C10 C8 H8 . . 106.2 ?
N1 C8 H8 . . 106.2 ?
C9 C8 H8 . . 106.2 ?
O3 C9 O2 . . 127.9(3) ?
O3 C9 C8 . . 114.6(3) ?
O2 C9 C8 . . 117.5(3) ?
C1 O1 H1 . . 109.5 ?
C12 S1 C11 . . 100.5(3) ?
C11 C10 C8 . . 108.8(4) ?
C11 C10 H10A . . 109.9 ?
C8 C10 H10A . . 109.9 ?
C11 C10 H10B . . 109.9 ?
C8 C10 H10B . . 109.9 ?
H10A C10 H10B . . 108.3 ?
C10 C11 S1 . . 110.1(4) ?
C10 C11 H11A . . 109.6 ?
S1 C11 H11A . . 109.6 ?
C10 C11 H11B . . 109.6 ?
S1 C11 H11B . . 109.6 ?
H11A C11 H11B . . 108.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.365(5) ?
C1 C2 . 1.389(5) ?
C1 C6 . 1.392(5) ?
C2 C3 . 1.387(7) ?
C2 H2 . 0.93 ?
C3 C4 . 1.360(7) ?
C3 H3 . 0.93 ?
C4 C5 . 1.375(7) ?
C4 H4 . 0.93 ?
C5 C6 . 1.388(6) ?
C5 H5 . 0.93 ?
C6 C7 . 1.484(6) ?
C7 N1 . 1.502(5) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
N1 C8 . 1.489(4) ?
N1 H1A . 0.9 ?
N1 H1B . 0.9 ?
C12 S1 . 1.749(8) ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C8 C10 . 1.483(7) ?
C8 C9 . 1.539(4) ?
C8 H8 . 0.98 ?
C9 O3 . 1.232(4) ?
C9 O2 . 1.246(5) ?
O1 H1 . 0.82 ?
S1 C11 . 2.023(7) ?
C10 C11 . 1.366(8) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O2 1_465 0.82 1.83 2.641(3) 168
N1 H1A O3 1_565 0.9 1.83 2.713(3) 166
N1 H1B O1 1_655 0.9 2.14 2.916(4) 144
N1 H1B O2 . 0.9 2.35 2.687(3) 102
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
O1 C1 C2 C3 . . . . -177.5(4) ?
C6 C1 C2 C3 . . . . 3.7(6) ?
C1 C2 C3 C4 . . . . -1.2(7) ?
C2 C3 C4 C5 . . . . -2.7(8) ?
C3 C4 C5 C6 . . . . 4.3(8) ?
C4 C5 C6 C1 . . . . -1.8(6) ?
C4 C5 C6 C7 . . . . 179.0(5) ?
O1 C1 C6 C5 . . . . 178.9(4) ?
C2 C1 C6 C5 . . . . -2.2(5) ?
O1 C1 C6 C7 . . . . -1.8(5) ?
C2 C1 C6 C7 . . . . 177.1(4) ?
C5 C6 C7 N1 . . . . -89.0(5) ?
C1 C6 C7 N1 . . . . 91.8(4) ?
C6 C7 N1 C8 . . . . -169.9(3) ?
C7 N1 C8 C10 . . . . 156.6(4) ?
C7 N1 C8 C9 . . . . -73.8(4) ?
C10 C8 C9 O3 . . . . -74.6(5) ?
N1 C8 C9 O3 . . . . 157.1(3) ?
C10 C8 C9 O2 . . . . 105.0(4) ?
N1 C8 C9 O2 . . . . -23.4(5) ?
N1 C8 C10 C11 . . . . 71.0(5) ?
C9 C8 C10 C11 . . . . -55.9(5) ?
C8 C10 C11 S1 . . . . -177.7(3) ?
C12 S1 C11 C10 . . . . 100.9(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5398106
