#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/30/2223077.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_2223077
loop_
_publ_author_name
'Chen, Wu'
'Liu, Lian'
'Xu, Di'
'Zeng, Qing-Fu'
_publ_section_title
;
 2-(2-Furylmethylaminomethyl)-4-sulfanylphenol
;
_journal_coeditor_code           HB5047
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2204
_journal_paper_doi               10.1107/S1600536809032401
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H13 N O2 S'
_chemical_formula_moiety         'C12 H13 N O2 S'
_chemical_formula_sum            'C12 H13 N O2 S'
_chemical_formula_weight         235.29
_chemical_name_systematic
;
2-(2-Furylmethylaminomethyl)-4-sulfanylphenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5778(12)
_cell_length_b                   13.589(3)
_cell_length_c                   14.943(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1132.6(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2528
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.457
_refine_ls_abs_structure_details 'Flack (1983), 900 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(17)
_refine_ls_extinction_coef       0.058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1031P)²+0.1612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1662
_reflns_number_gt                1811
_reflns_number_total             2216
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5047.cif
_cod_data_source_block           I
_cod_database_code               2223077
_cod_database_fobs_code          2223077
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 -0.2480(7) 0.7259(3) 0.4206(3) 0.0591(10) Uani d . 1 . .
H H1 -0.3948 0.7288 0.4501 0.071 Uiso calc R 1 . .
C C2 -0.1233(8) 0.6441(3) 0.4068(3) 0.0581(9) Uani d . 1 . .
H H2 -0.1659 0.5807 0.4239 0.070 Uiso calc R 1 . .
C C3 0.0881(8) 0.6728(3) 0.3607(3) 0.0564(10) Uani d . 1 . .
H H3 0.2108 0.6312 0.3420 0.068 Uiso calc R 1 . .
C C4 0.0791(6) 0.7696(3) 0.3490(2) 0.0480(8) Uani d . 1 . .
C C5 0.2431(8) 0.8424(3) 0.3079(3) 0.0600(10) Uani d . 1 . .
H H5A 0.2795 0.8933 0.3512 0.072 Uiso calc R 1 . .
H H5B 0.3923 0.8100 0.2920 0.072 Uiso calc R 1 . .
C C6 0.1385(8) 0.8197(2) 0.1507(2) 0.0526(9) Uani d . 1 . .
H H6A 0.0551 0.7597 0.1671 0.063 Uiso calc R 1 . .
H H6B 0.3023 0.8025 0.1354 0.063 Uiso calc R 1 . .
C C7 0.0183(6) 0.8652(2) 0.0710(2) 0.0422(8) Uani d . 1 . .
C C8 0.1130(6) 0.8552(2) -0.0141(2) 0.0449(8) Uani d . 1 . .
H H8 0.2558 0.8209 -0.0219 0.054 Uiso calc R 1 . .
C C9 -0.0009(7) 0.8953(3) -0.0874(3) 0.0481(8) Uani d . 1 . .
C C10 -0.2099(8) 0.9468(3) -0.0782(3) 0.0591(10) Uani d . 1 . .
H H10 -0.2856 0.9737 -0.1280 0.071 Uiso calc R 1 . .
C C11 -0.3069(7) 0.9583(3) 0.0062(3) 0.0613(11) Uani d . 1 . .
H H11 -0.4480 0.9939 0.0134 0.074 Uiso calc R 1 . .
C C12 -0.1958(6) 0.9172(3) 0.0804(3) 0.0502(9) Uani d . 1 . .
H H1C 0.230(9) 0.942(3) 0.212(3) 0.060 Uiso d . 1 . .
N N1 0.1391(7) 0.8878(2) 0.2275(2) 0.0550(8) Uani d . 1 . .
O O1 -0.1310(6) 0.8050(2) 0.38570(18) 0.0632(8) Uani d . 1 . .
O O2 -0.2984(5) 0.9310(2) 0.1623(2) 0.0696(8) Uani d . 1 . .
H H2A -0.2170 0.9038 0.2007 0.104 Uiso calc R 1 . .
S S1 0.1282(2) 0.88051(8) -0.19340(6) 0.0635(4) Uani d . 1 . .
H H1A 0.3423 0.8770 -0.1863 0.095 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 0.0000 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'
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
C2 C1 O1 . . 110.5(3) ?
C2 C1 H1 . . 124.8 ?
O1 C1 H1 . . 124.8 ?
C1 C2 C3 . . 106.3(4) ?
C1 C2 H2 . . 126.8 ?
C3 C2 H2 . . 126.8 ?
C4 C3 C2 . . 107.7(4) ?
C4 C3 H3 . . 126.1 ?
C2 C3 H3 . . 126.1 ?
C3 C4 O1 . . 108.9(3) ?
C3 C4 C5 . . 133.9(4) ?
O1 C4 C5 . . 117.2(3) ?
N1 C5 C4 . . 112.1(3) ?
N1 C5 H5A . . 109.2 ?
C4 C5 H5A . . 109.2 ?
N1 C5 H5B . . 109.2 ?
C4 C5 H5B . . 109.2 ?
H5A C5 H5B . . 107.9 ?
N1 C6 C7 . . 111.1(3) ?
N1 C6 H6A . . 109.4 ?
C7 C6 H6A . . 109.4 ?
N1 C6 H6B . . 109.4 ?
C7 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
C8 C7 C12 . . 118.0(3) ?
C8 C7 C6 . . 121.2(3) ?
C12 C7 C6 . . 120.7(3) ?
C9 C8 C7 . . 121.0(3) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C10 C9 C8 . . 121.1(4) ?
C10 C9 S1 . . 120.0(3) ?
C8 C9 S1 . . 118.9(3) ?
C9 C10 C11 . . 118.9(4) ?
C9 C10 H10 . . 120.6 ?
C11 C10 H10 . . 120.6 ?
C10 C11 C12 . . 120.6(4) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
O2 C12 C11 . . 118.3(3) ?
O2 C12 C7 . . 121.3(4) ?
C11 C12 C7 . . 120.4(4) ?
C5 N1 C6 . . 111.9(3) ?
C5 N1 H1C . . 109(3) ?
C6 N1 H1C . . 108(2) ?
C1 O1 C4 . . 106.5(3) ?
C12 O2 H2A . . 109.5 ?
C9 S1 H1A . . 109.5 ?
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 C2 . 1.328(6) ?
C1 O1 . 1.361(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.420(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.327(5) ?
C3 H3 . 0.9300 ?
C4 O1 . 1.381(5) ?
C4 C5 . 1.481(5) ?
C5 N1 . 1.470(5) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 N1 . 1.473(5) ?
C6 C7 . 1.501(5) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.383(5) ?
C7 C12 . 1.394(5) ?
C8 C9 . 1.379(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.366(6) ?
C9 S1 . 1.752(4) ?
C10 C11 . 1.382(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.388(6) ?
C11 H11 . 0.9300 ?
C12 O2 . 1.365(5) ?
N1 H1C . 0.93(5) ?
O2 H2A . 0.8200 ?
S1 H1A . 1.2000 ?
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
O2 H2A N1 . 0.82 2.04 2.692(5) 136
N1 H1C S1 2_575 0.93(5) 2.90(4) 3.605(3) 134(3)
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 . . . . 0.5(5) ?
C1 C2 C3 C4 . . . . -0.2(5) ?
C2 C3 C4 O1 . . . . -0.1(4) ?
C2 C3 C4 C5 . . . . 178.8(4) ?
C3 C4 C5 N1 . . . . 114.6(5) ?
O1 C4 C5 N1 . . . . -66.5(4) ?
N1 C6 C7 C8 . . . . 137.6(3) ?
N1 C6 C7 C12 . . . . -43.8(5) ?
C12 C7 C8 C9 . . . . -0.1(5) ?
C6 C7 C8 C9 . . . . 178.6(3) ?
C7 C8 C9 C10 . . . . 0.5(5) ?
C7 C8 C9 S1 . . . . 179.8(3) ?
C8 C9 C10 C11 . . . . 0.0(6) ?
S1 C9 C10 C11 . . . . -179.4(3) ?
C9 C10 C11 C12 . . . . -0.8(6) ?
C10 C11 C12 O2 . . . . 179.7(4) ?
C10 C11 C12 C7 . . . . 1.3(6) ?
C8 C7 C12 O2 . . . . -179.2(3) ?
C6 C7 C12 O2 . . . . 2.2(5) ?
C8 C7 C12 C11 . . . . -0.8(5) ?
C6 C7 C12 C11 . . . . -179.4(3) ?
C4 C5 N1 C6 . . . . -73.9(4) ?
C7 C6 N1 C5 . . . . 176.6(3) ?
C2 C1 O1 C4 . . . . -0.6(4) ?
C3 C4 O1 C1 . . . . 0.4(4) ?
C5 C4 O1 C1 . . . . -178.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743109
