#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/60/2206028.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_2206028
loop_
_publ_author_name
'K. A. Nirmala'
Vasu
'Deepak Chopra'
'S. Mohan'
'M. Raghu Prasad'
_publ_section_title
;Ethyl
 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1541
_journal_page_last               o1543
_journal_paper_doi               10.1107/S1600536805012808
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H17 N O2 S'
_chemical_formula_moiety         'C12 H17 N O2 S'
_chemical_formula_sum            'C12 H17 N O2 S'
_chemical_formula_weight         239.34
_chemical_name_systematic
;
Ethyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-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
_cell_angle_alpha                90
_cell_angle_beta                 99.489(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.580(3)
_cell_length_b                   9.552(2)
_cell_length_c                   13.677(4)
_cell_measurement_reflns_used    635
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      1.4
_cell_volume                     1234.4(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9377
_diffrn_reflns_reduction_process
;
 ?
;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  0.9661
_exptl_absorpt_correction_T_min  0.9178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0383
_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)+(0.0573P)²+0.2147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2221
_reflns_number_total             2487
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6500.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.

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1234.3(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206028
_cod_database_fobs_code          2206028
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
loop_
_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_occupancy
_atom_site_type_symbol
S1 0.25611(5) 0.17947(4) -0.10628(3) 0.04896(16) Uani d 1 S
O1 0.03961(12) 0.60020(11) -0.15671(8) 0.0528(3) Uani d 1 O
O2 0.14741(11) 0.65327(10) -0.00392(7) 0.0425(3) Uani d 1 O
N1 0.09238(19) 0.34733(17) -0.23394(10) 0.0590(4) Uani d 1 N
C1 0.41463(18) 0.15512(18) 0.08495(14) 0.0496(4) Uani d 1 C
C2 0.55979(18) 0.2232(2) 0.11716(15) 0.0598(5) Uani d 1 C
C3 0.5614(2) 0.3450(2) 0.18778(14) 0.0599(5) Uani d 1 C
C4 0.4744(2) 0.4727(2) 0.14909(13) 0.0552(4) Uani d 1 C
C5 0.31499(18) 0.44758(18) 0.12288(11) 0.0456(4) Uani d 1 C
C6 0.27150(14) 0.37440(14) 0.02496(9) 0.0339(3) Uani d 1 C
C7 0.31707(15) 0.24280(15) 0.01218(11) 0.0394(3) Uani d 1 C
C8 0.18273(14) 0.42880(13) -0.06361(9) 0.0339(3) Uani d 1 C
C9 0.16503(16) 0.33208(14) -0.14055(11) 0.0401(3) Uani d 1 C
C10 0.11639(14) 0.56516(14) -0.08002(10) 0.0354(3) Uani d 1 C
C11 0.08966(17) 0.79327(15) -0.01557(12) 0.0439(4) Uani d 1 C
C12 0.1438(2) 0.8687(2) 0.07877(16) 0.0601(5) Uani d 1 C
H1 0.041(2) 0.422(2) -0.2416(15) 0.067(6) Uiso d 1 H
H2 0.069(2) 0.275(2) -0.2670(16) 0.063(6) Uiso d 1 H
H3 0.2837(19) 0.388(2) 0.1748(14) 0.058(5) Uiso d 1 H
H4 0.265(2) 0.531(2) 0.1256(13) 0.058(5) Uiso d 1 H
H5 0.489(2) 0.543(2) 0.1986(17) 0.074(6) Uiso d 1 H
H6 0.509(2) 0.511(2) 0.0920(15) 0.061(5) Uiso d 1 H
H7 0.658(2) 0.373(2) 0.2047(16) 0.076(6) Uiso d 1 H
H8 0.527(2) 0.311(2) 0.2449(16) 0.064(6) Uiso d 1 H
H9 0.623(2) 0.150(2) 0.1508(15) 0.066(6) Uiso d 1 H
H10 0.593(2) 0.252(2) 0.0579(17) 0.068(6) Uiso d 1 H
H11 0.371(2) 0.137(2) 0.1442(15) 0.064(5) Uiso d 1 H
H12 0.4254(19) 0.061(2) 0.0568(14) 0.061(5) Uiso d 1 H
H13 0.243(3) 0.874(3) 0.0876(17) 0.082(7) Uiso d 1 H
H14 0.107(3) 0.823(2) 0.1343(19) 0.086(7) Uiso d 1 H
H15 0.113(2) 0.960(3) 0.0750(16) 0.077(6) Uiso d 1 H
H16 -0.012(2) 0.7870(18) -0.0266(12) 0.047(4) Uiso d 1 H
H17 0.1229(18) 0.8386(17) -0.0709(14) 0.046(4) Uiso d 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 '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
C9 S1 C7 92.09(7)
C10 O2 C11 117.75(11)
C7 C6 C8 112.40(12)
C7 C6 C5 119.90(12)
C8 C6 C5 127.70(12)
O1 C10 O2 121.42(13)
O1 C10 C8 124.34(13)
O2 C10 C8 114.23(11)
C9 C8 C10 118.96(12)
C9 C8 C6 111.99(12)
C10 C8 C6 129.05(12)
C6 C7 C1 127.70(14)
C6 C7 S1 112.23(10)
C1 C7 S1 120.01(12)
C9 N1 H1 113.4(14)
C9 N1 H2 118.2(14)
H1 N1 H2 121.2(19)
N1 C9 C8 128.37(14)
N1 C9 S1 120.30(12)
C8 C9 S1 111.30(10)
O2 C11 C12 106.19(13)
O2 C11 H16 108.6(10)
C12 C11 H16 111.3(10)
O2 C11 H17 109.3(10)
C12 C11 H17 110.3(10)
H16 C11 H17 111.0(15)
C6 C5 C4 113.60(14)
C6 C5 H3 107.2(11)
C4 C5 H3 109.3(10)
C6 C5 H4 111.2(11)
C4 C5 H4 110.9(12)
H3 C5 H4 104.2(15)
C7 C1 C2 112.94(14)
C7 C1 H11 109.9(11)
C2 C1 H11 108.9(12)
C7 C1 H12 110.0(11)
C2 C1 H12 110.5(11)
H11 C1 H12 104.2(16)
C3 C4 C5 115.09(15)
C3 C4 H5 108.0(13)
C5 C4 H5 107.6(13)
C3 C4 H6 109.8(12)
C5 C4 H6 109.6(12)
H5 C4 H6 106.4(17)
C11 C12 H14 109.6(14)
C11 C12 H15 110.3(14)
H14 C12 H15 107.9(19)
C11 C12 H13 109.6(14)
H14 C12 H13 114(2)
H15 C12 H13 106(2)
C2 C3 C4 116.60(15)
C2 C3 H8 107.1(12)
C4 C3 H8 108.4(12)
C2 C3 H7 106.1(13)
C4 C3 H7 108.4(13)
H8 C3 H7 110.2(18)
C3 C2 C1 115.06(16)
C3 C2 H10 110.3(13)
C1 C2 H10 106.8(12)
C3 C2 H9 107.8(12)
C1 C2 H9 107.0(12)
H10 C2 H9 109.6(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.7236(15)
S1 C7 1.7377(15)
O2 C10 1.3334(16)
O2 C11 1.4459(17)
O1 C10 1.2242(17)
C6 C7 1.351(2)
C6 C8 1.4563(18)
C6 C5 1.5072(19)
C10 C8 1.4505(19)
C8 C9 1.3895(19)
C7 C1 1.503(2)
N1 C9 1.358(2)
N1 H1 0.87(2)
N1 H2 0.83(2)
C11 C12 1.494(2)
C11 H16 0.964(18)
C11 H17 0.970(18)
C5 C4 1.529(2)
C5 H3 1.00(2)
C5 H4 0.929(19)
C1 C2 1.532(3)
C1 H11 0.99(2)
C1 H12 0.99(2)
C4 C3 1.523(3)
C4 H5 0.94(2)
C4 H6 0.97(2)
C12 H14 0.99(2)
C12 H15 0.92(2)
C12 H13 0.94(3)
C3 C2 1.511(3)
C3 H8 0.95(2)
C3 H7 0.95(2)
C2 H10 0.96(2)
C2 H9 0.99(2)
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
_geom_hbond_publ_flag
N1 H1 O1 1_555 0.87(2) 2.06(2) 2.717(2) 132(2) yes
N1 H2 O1 2_544 0.84(2) 2.15(2) 2.964(2) 166(2) yes
C5 H4 O2 1_555 0.93(2) 2.27(2) 2.920(2) 127.0(10) yes
C11 H16 Cg1 3_565 0.96(2) 2.76 3.578 143 yes
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
C11 O2 C10 O1 -1.3(2) ?
C11 O2 C10 C8 177.79(12) yes
O1 C10 C8 C9 3.2(2) yes
O2 C10 C8 C9 -175.81(12) ?
O1 C10 C8 C6 -177.77(14) ?
O2 C10 C8 C6 3.2(2) yes
C7 C6 C8 C9 0.32(17) ?
C5 C6 C8 C9 179.85(14) ?
C7 C6 C8 C10 -178.73(13) ?
C5 C6 C8 C10 0.8(2) ?
C8 C6 C7 C1 177.33(14) ?
C5 C6 C7 C1 -2.2(2) yes
C8 C6 C7 S1 0.23(15) ?
C5 C6 C7 S1 -179.34(11) ?
C9 S1 C7 C6 -0.55(12) ?
C9 S1 C7 C1 -177.90(13) ?
C10 C8 C9 N1 0.8(2) ?
C6 C8 C9 N1 -178.39(16) ?
C10 C8 C9 S1 178.43(10) ?
C6 C8 C9 S1 -0.72(15) ?
C7 S1 C9 N1 178.61(14) ?
C7 S1 C9 C8 0.73(12) ?
C10 O2 C11 C12 -178.65(15) yes
C7 C6 C5 C4 63.50(19) ?
C8 C6 C5 C4 -116.00(16) ?
C6 C7 C1 C2 -59.2(2) ?
S1 C7 C1 C2 117.67(15) ?
C6 C5 C4 C3 -77.66(19) yes
C5 C4 C3 C2 63.2(2) ?
C4 C3 C2 C1 -62.9(2) ?
C7 C1 C2 C3 73.9(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 258244
