#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/30/2213064.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_2213064
loop_
_publ_author_name
'Bourgeaux, Marie'
'Skene, W.G.'
_publ_section_title
;
 Ethyl 2-aminothiophene-3-carboxylate
;
_journal_coeditor_code           XU2214
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1603
_journal_page_last               o1605
_journal_paper_doi               10.1107/S1600536807009683
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H9 N O2 S'
_chemical_formula_moiety         'C7 H9 N O2 S'
_chemical_formula_sum            'C7 H9 N O2 S'
_chemical_formula_weight         171.21
_chemical_melting_point          .32E-305
_chemical_name_systematic
;
Ethyl 2-aminothiophene-3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 119.1920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.18380(10)
_cell_length_b                   17.8042(2)
_cell_length_c                   10.30460(10)
_cell_measurement_reflns_used    4685
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.9
_cell_measurement_theta_min      2.5
_cell_volume                     1631.07(3)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Bruker SMART 2K/PLATFORM'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13274
_diffrn_reflns_theta_full        72.9
_diffrn_reflns_theta_max         72.9
_diffrn_reflns_theta_min         4.9
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.132
_exptl_absorpt_correction_T_max  0.684
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       acicular
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.110
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                2714
_reflns_number_total             3207
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2214.cif
_cod_data_source_block           I
_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.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (13
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (27 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (13
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (27 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213064
_cod_database_fobs_code          2213064
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S S1 0.37538(5) 0.19527(3) 0.08000(5) 0.02045(15) Uani d . 1
N N11 0.47023(18) 0.09828(9) -0.05810(18) 0.0236(4) Uani d . 1
H H11A 0.5358 0.0814 -0.0834 0.028 Uiso calc R 1
H H11B 0.3848 0.0743 -0.0871 0.028 Uiso calc R 1
C C11 0.5006(2) 0.16104(10) 0.02524(19) 0.0176(4) Uani d . 1
C C12 0.6285(2) 0.20595(10) 0.08077(19) 0.0169(4) Uani d . 1
C C13 0.6207(2) 0.26872(10) 0.16451(19) 0.0179(4) Uani d . 1
H H13 0.6979 0.3054 0.2091 0.022 Uiso calc R 1
C C14 0.4928(2) 0.27047(10) 0.1736(2) 0.0205(4) Uani d . 1
H H14 0.4697 0.3081 0.2247 0.025 Uiso calc R 1
C C15 0.7509(2) 0.18877(9) 0.05265(19) 0.0159(4) Uani d . 1
O O15 0.75399(14) 0.13410(7) -0.01872(14) 0.0196(3) Uani d . 1
O O16 0.86169(14) 0.23974(7) 0.11152(14) 0.0195(3) Uani d . 1
C C16 0.9822(2) 0.23249(10) 0.0755(2) 0.0200(4) Uani d . 1
H H16A 0.9428 0.2387 -0.0327 0.024 Uiso calc R 1
H H16B 1.0301 0.1825 0.1055 0.024 Uiso calc R 1
C C17 1.0937(2) 0.29341(11) 0.1603(2) 0.0246(4) Uani d . 1
H H17A 1.0450 0.3425 0.1283 0.037 Uiso calc R 1
H H17B 1.1787 0.2904 0.1409 0.037 Uiso calc R 1
H H17C 1.1301 0.2870 0.2669 0.037 Uiso calc R 1
S S2 -0.29162(5) 0.52732(3) 0.24748(5) 0.02364(15) Uani d . 1
C C21 -0.1165(2) 0.49248(10) 0.28793(19) 0.0182(4) Uani d . 1
N N21 -0.06192(19) 0.42946(9) 0.36915(18) 0.0227(3) Uani d . 1
H H21A 0.0255 0.4114 0.3863 0.027 Uiso calc R 1
H H21B -0.1137 0.4064 0.4050 0.027 Uiso calc R 1
C C22 -0.0520(2) 0.53645(10) 0.22249(19) 0.0178(4) Uani d . 1
C C23 -0.1472(2) 0.59752(10) 0.1385(2) 0.0214(4) Uani d . 1
H H23 -0.1209 0.6328 0.0859 0.026 Uiso calc R 1
C C24 -0.2783(2) 0.59998(11) 0.1417(2) 0.0251(4) Uani d . 1
H H24 -0.3539 0.6369 0.0922 0.030 Uiso calc R 1
C C25 0.0943(2) 0.51810(10) 0.23973(19) 0.0171(4) Uani d . 1
O O25 0.17364(15) 0.46643(7) 0.31678(15) 0.0219(3) Uani d . 1
O O26 0.13526(14) 0.56322(7) 0.16113(14) 0.0197(3) Uani d . 1
C C26 0.2756(2) 0.54380(10) 0.1644(2) 0.0200(4) Uani d . 1
H H26A 0.2695 0.4925 0.1246 0.024 Uiso calc R 1
H H26B 0.3601 0.5454 0.2676 0.024 Uiso calc R 1
C C27 0.2997(2) 0.60039(11) 0.0697(2) 0.0225(4) Uani d . 1
H H27A 0.2118 0.6010 -0.0301 0.034 Uiso calc R 1
H H27B 0.3893 0.5868 0.0629 0.034 Uiso calc R 1
H H27C 0.3135 0.6503 0.1146 0.034 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
C11 S1 C14 92.01(9) n
C11 N11 H11A 120 n
C11 N11 H11B 120 n
H11A N11 H11B 120 n
N11 C11 C12 128.00(17) n
N11 C11 S1 121.32(14) n
C12 C11 S1 110.68(13) n
C11 C12 C13 112.26(16) n
C11 C12 C15 121.49(16) n
C13 C12 C15 126.25(16) n
C14 C13 C12 113.38(16) n
C14 C13 H13 123.3 n
C12 C13 H13 123.3 n
C13 C14 S1 111.66(14) n
C13 C14 H14 124.2 n
S1 C14 H14 124.2 n
O15 C15 O16 123.02(17) n
O15 C15 C12 124.37(16) n
O16 C15 C12 112.61(15) n
C15 O16 C16 117.02(14) n
O16 C16 C17 106.27(14) n
O16 C16 H16A 110.5 n
C17 C16 H16A 110.5 n
O16 C16 H16B 110.5 n
C17 C16 H16B 110.5 n
H16A C16 H16B 108.7 n
C16 C17 H17A 109.5 n
C16 C17 H17B 109.5 n
H17A C17 H17B 109.5 n
C16 C17 H17C 109.5 n
H17A C17 H17C 109.5 n
H17B C17 H17C 109.5 n
C21 S2 C24 91.77(9) n
N21 C21 C22 128.42(18) n
N21 C21 S2 120.72(14) n
C22 C21 S2 110.84(14) n
C21 N21 H21A 120 n
C21 N21 H21B 120 n
H21A N21 H21B 120 n
C21 C22 C23 112.29(17) n
C21 C22 C25 120.97(16) n
C23 C22 C25 126.72(17) n
C24 C23 C22 113.31(17) n
C24 C23 H23 123.3 n
C22 C23 H23 123.3 n
C23 C24 S2 111.78(15) n
C23 C24 H24 124.1 n
S2 C24 H24 124.1 n
O25 C25 O26 122.62(16) n
O25 C25 C22 124.17(17) n
O26 C25 C22 113.21(15) n
C25 O26 C26 115.75(14) n
O26 C26 C27 107.16(15) n
O26 C26 H26A 110.3 n
C27 C26 H26A 110.3 n
O26 C26 H26B 110.3 n
C27 C26 H26B 110.3 n
H26A C26 H26B 108.5 n
C26 C27 H27A 109.5 n
C26 C27 H27B 109.5 n
H27A C27 H27B 109.5 n
C26 C27 H27C 109.5 n
H27A C27 H27C 109.5 n
H27B C27 H27C 109.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C11 1.7377(18) y
S1 C14 1.7398(19) y
N11 C11 1.350(2) y
N11 H11A 0.88 n
N11 H11B 0.88 n
C11 C12 1.391(2) y
C12 C13 1.438(2) y
C12 C15 1.443(3) n
C13 C14 1.351(3) y
C13 H13 0.95 n
C14 H14 0.95 n
C15 O15 1.230(2) n
C15 O16 1.341(2) n
O16 C16 1.451(2) n
C16 C17 1.504(2) n
C16 H16A 0.99 n
C16 H16B 0.99 n
C17 H17A 0.98 n
C17 H17B 0.98 n
C17 H17C 0.98 n
S2 C21 1.7363(19) y
S2 C24 1.739(2) y
C21 N21 1.347(2) y
C21 C22 1.390(3) y
N21 H21A 0.88 n
N21 H21B 0.88 n
C22 C23 1.433(2) y
C22 C25 1.449(3) y
C23 C24 1.351(3) y
C23 H23 0.95 n
C24 H24 0.95 n
C25 O25 1.226(2) n
C25 O26 1.343(2) n
O26 C26 1.455(2) n
C26 C27 1.503(2) n
C26 H26A 0.99 n
C26 H26B 0.99 n
C27 H27A 0.98 n
C27 H27B 0.98 n
C27 H27C 0.98 n
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
N11 H11A O15 . 0.88 2.19 2.789(2) 124
N11 H11B O25 4_565 0.88 2.01 2.883(2) 170
N21 H21A O25 . 0.88 2.19 2.782(2) 124
N21 H21B O15 4_466 0.88 1.99 2.871(2) 173
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
_geom_torsion_publ_flag
C14 S1 C11 N11 -179.77(16) n
C14 S1 C11 C12 1.15(14) n
N11 C11 C12 C13 179.65(17) n
S1 C11 C12 C13 -1.34(18) n
N11 C11 C12 C15 0.1(3) n
S1 C11 C12 C15 179.10(13) n
C11 C12 C13 C14 0.9(2) n
C15 C12 C13 C14 -179.60(17) n
C12 C13 C14 S1 0.0(2) n
C11 S1 C14 C13 -0.67(15) n
C11 C12 C15 O15 -1.1(3) n
C13 C12 C15 O15 179.42(17) n
C11 C12 C15 O16 178.12(15) n
C13 C12 C15 O16 -1.4(2) y
O15 C15 O16 C16 6.0(2) n
C12 C15 O16 C16 -173.19(14) n
C15 O16 C16 C17 -177.35(15) n
C24 S2 C21 N21 -177.61(16) n
C24 S2 C21 C22 0.56(14) n
N21 C21 C22 C23 177.24(18) n
S2 C21 C22 C23 -0.7(2) n
N21 C21 C22 C25 -1.6(3) n
S2 C21 C22 C25 -179.55(13) n
C21 C22 C23 C24 0.6(2) n
C25 C22 C23 C24 179.32(17) n
C22 C23 C24 S2 -0.2(2) n
C21 S2 C24 C23 -0.22(16) n
C21 C22 C25 O25 -3.7(3) n
C23 C22 C25 O25 177.64(17) n
C21 C22 C25 O26 175.68(15) n
C23 C22 C25 O26 -2.9(3) y
O25 C25 O26 C26 4.2(2) n
C22 C25 O26 C26 -175.22(14) n
C25 O26 C26 C27 179.64(14) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1511095
