#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/67/2236777.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_2236777
loop_
_publ_author_name
'Kantar, Esen Nur'
'Köysal, Yavuz'
'Macit, Mustafa'
'Er, Ebru'
'Soylu, Mustafa Serkan'
_publ_section_title
;
 4-Methoxy-2-{(E)-[(thiophen-2-yl)methylimino]methyl}phenol
;
_journal_coeditor_code           ZQ2177
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2801
_journal_paper_doi               10.1107/S1600536812036586
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H13 N O2 S'
_chemical_formula_moiety         'C13 H13 N O2 S'
_chemical_formula_sum            'C13 H13 N O2 S'
_chemical_formula_weight         247.30
_chemical_name_systematic
;
4-Methoxy-2-{(E)-[(thiophen-2-yl)methylimino]methyl}phenol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 96.798(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.6325(3)
_cell_length_b                   8.1666(3)
_cell_length_c                   13.4836(6)
_cell_measurement_reflns_used    958
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      3.64
_cell_volume                     615.86(5)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0454
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova (single source at offset) Eos'
_diffrn_measurement_method       'ω 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  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2221
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.205
_refine_ls_abs_structure_details 'Flack (1983), 640 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1809
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0439P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                1472
_reflns_number_total             1809
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zq2177.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2236777
_cod_database_fobs_code          2236777
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
C C1 0.3932(6) 0.8415(4) 0.5974(3) 0.0481(9) Uani d . 1 1
C C2 0.4982(7) 0.9033(4) 0.5174(3) 0.0551(10) Uani d . 1 1
H H2 0.6417 0.9604 0.5289 0.066 Uiso calc R 1 1
C C3 0.3927(7) 0.8808(4) 0.4220(3) 0.0562(10) Uani d . 1 1
H H3 0.4663 0.9221 0.3691 0.067 Uiso calc R 1 1
C C4 0.1768(7) 0.7970(4) 0.4023(3) 0.0500(9) Uani d . 1 1
C C5 0.0698(7) 0.7362(4) 0.4812(2) 0.0449(9) Uani d . 1 1
H H5 -0.0738 0.6795 0.4689 0.054 Uiso calc R 1 1
C C6 0.1748(6) 0.7589(4) 0.5800(2) 0.0415(8) Uani d . 1 1
C C7 0.0515(7) 0.6993(4) 0.6618(3) 0.0440(9) Uani d . 1 1
H H7 -0.0921 0.6433 0.6472 0.053 Uiso calc R 1 1
C C8 -0.0063(7) 0.6629(5) 0.8305(3) 0.0586(11) Uani d . 1 1
H H8A -0.1025 0.5702 0.8050 0.070 Uiso calc R 1 1
H H8B -0.1139 0.7489 0.8468 0.070 Uiso calc R 1 1
C C9 0.1489(7) 0.6132(4) 0.9223(3) 0.0506(9) Uani d . 1 1
C C10 0.1217(7) 0.6557(5) 1.0203(3) 0.0562(10) Uani d U 1 1
H H10 0.0014 0.7232 1.0389 0.067 Uiso calc R 1 1
C C11 0.3051(8) 0.5809(6) 1.0888(3) 0.0726(13) Uani d U 1 1
H H11 0.3178 0.5960 1.1576 0.087 Uiso calc R 1 1
C C12 0.4554(8) 0.4878(7) 1.0440(3) 0.0725(12) Uani d . 1 1
H H12 0.5821 0.4302 1.0781 0.087 Uiso calc R 1 1
C C13 -0.1056(9) 0.6748(6) 0.2794(3) 0.0737(13) Uani d . 1 1
H H13A -0.1514 0.6756 0.2085 0.111 Uiso calc R 1 1
H H13B -0.2383 0.7091 0.3128 0.111 Uiso calc R 1 1
H H13C -0.0587 0.5661 0.3004 0.111 Uiso calc R 1 1
N N1 0.1345(6) 0.7215(4) 0.7533(2) 0.0528(8) Uani d . 1 1
O O1 0.5060(5) 0.8643(3) 0.6917(2) 0.0659(8) Uani d . 1 1
O O2 0.0879(6) 0.7829(3) 0.30331(18) 0.0652(8) Uani d . 1 1
S S1 0.3895(2) 0.48631(16) 0.91768(8) 0.0757(4) Uani d . 1 1
H H1 0.386(11) 0.814(9) 0.743(4) 0.17(2) Uiso d . 1 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
O1 C1 C2 118.7(3)
O1 C1 C6 121.7(3)
C2 C1 C6 119.6(3)
C3 C2 C1 120.4(4)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 121.2(4)
C2 C3 H3 119.4
C4 C3 H3 119.4
O2 C4 C5 125.3(4)
O2 C4 C3 115.8(3)
C5 C4 C3 118.8(3)
C4 C5 C6 120.8(3)
C4 C5 H5 119.6
C6 C5 H5 119.6
C5 C6 C1 119.1(3)
C5 C6 C7 119.4(3)
C1 C6 C7 121.5(3)
N1 C7 C6 122.1(3)
N1 C7 H7 119.0
C6 C7 H7 119.0
N1 C8 C9 111.6(3)
N1 C8 H8A 109.3
C9 C8 H8A 109.3
N1 C8 H8B 109.3
C9 C8 H8B 109.3
H8A C8 H8B 108.0
C10 C9 C8 127.1(4)
C10 C9 S1 111.2(3)
C8 C9 S1 121.7(3)
C9 C10 C11 110.6(4)
C9 C10 H10 124.7
C11 C10 H10 124.7
C12 C11 C10 113.4(4)
C12 C11 H11 123.3
C10 C11 H11 123.3
C11 C12 S1 112.5(3)
C11 C12 H12 123.7
S1 C12 H12 123.7
O2 C13 H13A 109.5
O2 C13 H13B 109.5
H13A C13 H13B 109.5
O2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C7 N1 C8 118.2(3)
C1 O1 H1 106(3)
C4 O2 C13 117.3(3)
C12 S1 C9 92.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.365(4)
C1 C2 1.385(5)
C1 C6 1.398(5)
C2 C3 1.364(5)
C2 H2 0.9300
C3 C4 1.393(5)
C3 H3 0.9300
C4 O2 1.374(4)
C4 C5 1.375(5)
C5 C6 1.404(4)
C5 H5 0.9300
C6 C7 1.456(4)
C7 N1 1.279(4)
C7 H7 0.9300
C8 N1 1.462(4)
C8 C9 1.486(5)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.392(5)
C9 S1 1.713(4)
C10 C11 1.438(5)
C10 H10 0.9300
C11 C12 1.334(6)
C11 H11 0.9300
C12 S1 1.699(4)
C12 H12 0.9300
C13 O2 1.410(5)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
O1 H1 1.10(6)
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 N1 . 1.10(6) 1.63(7) 2.616(4) 147(5)
C8 H8A O2 2_546 0.97 2.77 3.592(4) 143
C2 H2 Cg1 2_656 0.93 3.00 3.631(4) 127
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
O1 C1 C2 C3 179.0(3)
C6 C1 C2 C3 -1.5(5)
C1 C2 C3 C4 0.6(5)
C2 C3 C4 O2 179.7(3)
C2 C3 C4 C5 -0.1(5)
O2 C4 C5 C6 -179.3(3)
C3 C4 C5 C6 0.4(5)
C4 C5 C6 C1 -1.3(5)
C4 C5 C6 C7 177.3(3)
O1 C1 C6 C5 -178.7(3)
C2 C1 C6 C5 1.8(5)
O1 C1 C6 C7 2.7(5)
C2 C1 C6 C7 -176.8(3)
C5 C6 C7 N1 -177.5(3)
C1 C6 C7 N1 1.1(5)
N1 C8 C9 C10 132.6(4)
N1 C8 C9 S1 -49.0(5)
C8 C9 C10 C11 178.8(3)
S1 C9 C10 C11 0.3(4)
C9 C10 C11 C12 -0.8(6)
C10 C11 C12 S1 0.9(5)
C6 C7 N1 C8 177.7(3)
C9 C8 N1 C7 149.1(3)
C5 C4 O2 C13 -11.4(5)
C3 C4 O2 C13 168.9(3)
C11 C12 S1 C9 -0.6(4)
C10 C9 S1 C12 0.1(3)
C8 C9 S1 C12 -178.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658198
