#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227459.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227459
loop_
_publ_author_name
'Mukhtar, Asma'
'Tahir, M. Nawaz'
'Khan, Misbahul Ain'
'Khan, Muhammad Naeem'
_publ_section_title
;
 Ethyl 2-benzamido-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2652
_journal_paper_doi               10.1107/S1600536810037761
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H19 N O3 S'
_chemical_formula_moiety         'C18 H19 N O3 S'
_chemical_formula_sum            'C18 H19 N O3 S'
_chemical_formula_weight         329.40
_chemical_name_systematic
;
Ethyl 2-benzamido-4,5,6,7-tetrahydro-1-benzothiophene-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           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 92.5000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1061(2)
_cell_length_b                   10.6593(3)
_cell_length_c                   19.0554(5)
_cell_measurement_reflns_used    2052
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.52
_cell_volume                     1644.92(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.10
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12204
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.195
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0417
_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)+(0.0503P)²+0.4332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                2052
_reflns_number_total             2964
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2302.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227459
_cod_database_fobs_code          2227459
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.75739(8) 0.64947(6) 0.09851(3) 0.0685(2) Uani . . 1.000
O O1 0.9000(2) 0.82309(16) 0.01442(9) 0.0875(7) Uani . . 1.000
O O2 0.8026(2) 0.41537(14) -0.09850(7) 0.0658(6) Uani . . 1.000
O O3 0.6816(2) 0.26412(14) -0.03830(7) 0.0666(6) Uani . . 1.000
N N1 0.8625(2) 0.63457(16) -0.03524(8) 0.0527(6) Uani . . 1.000
C C1 0.9770(3) 0.8019(2) -0.10411(11) 0.0545(7) Uani . . 1.000
C C2 0.9702(3) 0.7346(2) -0.16629(12) 0.0679(9) Uani . . 1.000
C C3 1.0262(3) 0.7864(3) -0.22706(13) 0.0781(10) Uani . . 1.000
C C4 1.0909(3) 0.9047(3) -0.22675(14) 0.0804(11) Uani . . 1.000
C C5 1.1013(3) 0.9711(3) -0.16569(16) 0.0830(11) Uani . . 1.000
C C6 1.0438(3) 0.9216(2) -0.10479(13) 0.0697(9) Uani . . 1.000
C C7 0.9121(3) 0.7563(2) -0.03689(12) 0.0582(8) Uani . . 1.000
C C8 0.7865(2) 0.5770(2) 0.01970(10) 0.0484(7) Uani . . 1.000
C C9 0.7256(2) 0.45660(19) 0.01795(10) 0.0464(7) Uani . . 1.000
C C10 0.6520(2) 0.4227(2) 0.08292(10) 0.0505(7) Uani . . 1.000
C C11 0.5695(3) 0.2999(2) 0.09967(11) 0.0615(8) Uani . . 1.000
C C12A 0.5302(8) 0.2864(5) 0.1768(3) 0.0771(13) Uani . . 0.641(6)
C C13A 0.4684(7) 0.4071(4) 0.2069(3) 0.0771(13) Uani . . 0.641(6)
C C14 0.5952(3) 0.5146(3) 0.20270(12) 0.0820(10) Uani . . 1.000
C C15 0.6620(3) 0.5167(2) 0.12986(11) 0.0601(8) Uani . . 1.000
C C16 0.7408(3) 0.3798(2) -0.04470(11) 0.0518(7) Uani . . 1.000
C C17 0.6953(4) 0.1819(2) -0.09806(13) 0.0804(10) Uani . . 1.000
C C18 0.6130(4) 0.0615(3) -0.08052(16) 0.1017(13) Uani . . 1.000
C C12B 0.4639(11) 0.3191(11) 0.1642(4) 0.0771(13) Uani . . 0.359(6)
C C13B 0.5564(13) 0.3883(8) 0.2231(4) 0.0771(13) Uani . . 0.359(6)
H H1 0.88006 0.58943 -0.07157 0.0632 Uiso . . 1.000
H H4 1.12771 0.93963 -0.26797 0.0964 Uiso . . 1.000
H H2 0.92751 0.65362 -0.16705 0.0815 Uiso . . 1.000
H H3 1.01981 0.74051 -0.26860 0.0936 Uiso . . 1.000
H H11A 0.64111 0.23142 0.08692 0.0738 Uiso . . 1.000
H H11B 0.46774 0.29269 0.07120 0.0738 Uiso . . 1.000
H H12A 0.44709 0.22178 0.18136 0.0926 Uiso . . 0.641(6)
H H12B 0.62887 0.26010 0.20338 0.0926 Uiso . . 0.641(6)
H H13A 0.44302 0.39369 0.25557 0.0926 Uiso . . 0.641(6)
H H13B 0.36703 0.43138 0.18147 0.0926 Uiso . . 0.641(6)
H H14A 0.54276 0.59409 0.21247 0.0985 Uiso . . 1.000
H H14B 0.68476 0.50168 0.23738 0.0985 Uiso . . 1.000
H H17A 0.81052 0.16736 -0.10724 0.0962 Uiso . . 1.000
H H17B 0.64183 0.21915 -0.13955 0.0962 Uiso . . 1.000
H H18A 0.66559 0.02642 -0.03888 0.1525 Uiso . . 1.000
H H18B 0.62180 0.00366 -0.11881 0.1525 Uiso . . 1.000
H H18C 0.49861 0.07682 -0.07259 0.1525 Uiso . . 1.000
H H5 1.14776 1.05084 -0.16517 0.0996 Uiso . . 1.000
H H6 1.04969 0.96880 -0.06371 0.0837 Uiso . . 1.000
H H12C 0.36549 0.36616 0.15021 0.0926 Uiso . . 0.359(6)
H H12D 0.42929 0.23798 0.18130 0.0926 Uiso . . 0.359(6)
H H13C 0.48949 0.39036 0.26402 0.0926 Uiso . . 0.359(6)
H H13D 0.65770 0.34371 0.23564 0.0926 Uiso . . 0.359(6)
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 C15 . . . 90.83(10) no
C16 O3 C17 . . . 116.70(17) no
C7 N1 C8 . . . 125.72(18) no
C7 N1 H1 . . . 117.00 no
C8 N1 H1 . . . 117.00 no
C2 C1 C6 . . . 118.0(2) no
C2 C1 C7 . . . 124.4(2) no
C6 C1 C7 . . . 117.5(2) no
C1 C2 C3 . . . 120.6(2) no
C2 C3 C4 . . . 120.5(2) no
C3 C4 C5 . . . 119.6(3) no
C4 C5 C6 . . . 120.8(3) no
C1 C6 C5 . . . 120.5(2) no
O1 C7 C1 . . . 123.0(2) no
O1 C7 N1 . . . 120.4(2) no
N1 C7 C1 . . . 116.61(19) no
S1 C8 C9 . . . 112.26(14) no
S1 C8 N1 . . . 123.14(16) no
N1 C8 C9 . . . 124.60(18) no
C8 C9 C16 . . . 120.08(17) no
C10 C9 C16 . . . 127.95(18) no
C8 C9 C10 . . . 111.98(17) no
C11 C10 C15 . . . 121.34(18) no
C9 C10 C11 . . . 126.98(18) no
C9 C10 C15 . . . 111.67(19) no
C10 C11 C12B . . . 108.7(5) no
C10 C11 C12A . . . 113.5(3) no
C11 C12A C13A . . . 112.0(4) no
C11 C12B C13B . . . 112.4(7) no
C12A C13A C14 . . . 112.4(4) no
C12B C13B C14 . . . 111.2(7) no
C13A C14 C15 . . . 108.9(3) no
C13B C14 C15 . . . 110.7(4) no
S1 C15 C10 . . . 113.26(16) no
S1 C15 C14 . . . 120.80(18) no
C10 C15 C14 . . . 125.9(2) no
O2 C16 C9 . . . 124.47(19) no
O3 C16 C9 . . . 113.69(18) no
O2 C16 O3 . . . 121.84(19) no
O3 C17 C18 . . . 107.2(2) no
C1 C2 H2 . . . 120.00 no
C3 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C10 C11 H11A . . . 109.00 no
C10 C11 H11B . . . 109.00 no
C12A C11 H11A . . . 109.00 no
C12A C11 H11B . . . 109.00 no
H11A C11 H11B . . . 108.00 no
C12B C11 H11A . . . 131.00 no
C12B C11 H11B . . . 88.00 no
C11 C12A H12A . . . 109.00 no
C11 C12A H12B . . . 109.00 no
C13A C12A H12A . . . 109.00 no
C13A C12A H12B . . . 109.00 no
H12A C12A H12B . . . 108.00 no
C13B C12B H12C . . . 109.00 no
C11 C12B H12C . . . 109.00 no
C11 C12B H12D . . . 109.00 no
C13B C12B H12D . . . 109.00 no
H12C C12B H12D . . . 108.00 no
C12A C13A H13A . . . 109.00 no
C14 C13A H13A . . . 109.00 no
C14 C13A H13B . . . 109.00 no
C12A C13A H13B . . . 109.00 no
H13A C13A H13B . . . 108.00 no
C14 C13B H13C . . . 109.00 no
C14 C13B H13D . . . 109.00 no
C12B C13B H13C . . . 109.00 no
C12B C13B H13D . . . 109.00 no
H13C C13B H13D . . . 108.00 no
C13A C14 H14A . . . 110.00 no
C13A C14 H14B . . . 110.00 no
C15 C14 H14A . . . 110.00 no
C13B C14 H14A . . . 131.00 no
C13B C14 H14B . . . 81.00 no
C15 C14 H14B . . . 110.00 no
H14A C14 H14B . . . 108.00 no
C18 C17 H17A . . . 110.00 no
O3 C17 H17A . . . 110.00 no
O3 C17 H17B . . . 110.00 no
H17A C17 H17B . . . 109.00 no
C18 C17 H17B . . . 110.00 no
C17 C18 H18C . . . 109.00 no
C17 C18 H18B . . . 109.00 no
H18B C18 H18C . . . 109.00 no
H18A C18 H18B . . . 109.00 no
H18A C18 H18C . . . 109.00 no
C17 C18 H18A . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . . 1.714(2) no
S1 C15 . . 1.732(2) no
O1 C7 . . 1.217(3) no
O2 C16 . . 1.221(3) no
O3 C16 . . 1.331(3) no
O3 C17 . . 1.445(3) no
N1 C7 . . 1.359(3) no
N1 C8 . . 1.381(2) no
N1 H1 . . 0.8600 no
C1 C2 . . 1.384(3) no
C1 C6 . . 1.386(3) no
C1 C7 . . 1.488(3) no
C2 C3 . . 1.378(3) no
C3 C4 . . 1.366(4) no
C4 C5 . . 1.361(4) no
C5 C6 . . 1.375(4) no
C8 C9 . . 1.375(3) no
C9 C10 . . 1.444(3) no
C9 C16 . . 1.457(3) no
C10 C15 . . 1.343(3) no
C10 C11 . . 1.510(3) no
C11 C12A . . 1.524(6) no
C11 C12B . . 1.542(8) no
C12A C13A . . 1.503(7) no
C12B C13B . . 1.514(12) no
C13A C14 . . 1.544(6) no
C13B C14 . . 1.440(9) no
C14 C15 . . 1.512(3) no
C17 C18 . . 1.491(4) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C11 H11A . . 0.9700 no
C11 H11B . . 0.9700 no
C12A H12A . . 0.9700 no
C12A H12B . . 0.9700 no
C12B H12D . . 0.9700 no
C12B H12C . . 0.9700 no
C13A H13B . . 0.9700 no
C13A H13A . . 0.9700 no
C13B H13C . . 0.9700 no
C13B H13D . . 0.9700 no
C14 H14A . . 0.9700 no
C14 H14B . . 0.9700 no
C17 H17A . . 0.9700 no
C17 H17B . . 0.9700 no
C18 H18B . . 0.9600 no
C18 H18C . . 0.9600 no
C18 H18A . . 0.9600 no
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 O2 . 0.86 2.02 2.664(2) 131 yes
C6 H6 O1 3_775 0.93 2.44 3.242(3) 145 yes
C11 H11A O3 . 0.97 2.45 2.845(3) 104 no
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
C15 S1 C8 N1 . . . . 179.88(17) no
C15 S1 C8 C9 . . . . -0.02(15) no
C8 S1 C15 C10 . . . . -0.32(18) no
C8 S1 C15 C14 . . . . -178.7(2) no
C17 O3 C16 O2 . . . . 0.5(3) no
C17 O3 C16 C9 . . . . -178.9(2) no
C16 O3 C17 C18 . . . . -176.8(2) no
C8 N1 C7 O1 . . . . 4.4(3) no
C8 N1 C7 C1 . . . . -174.38(19) no
C7 N1 C8 S1 . . . . -5.3(3) no
C7 N1 C8 C9 . . . . 174.55(19) no
C6 C1 C2 C3 . . . . -0.9(4) no
C7 C1 C2 C3 . . . . 176.9(2) no
C2 C1 C6 C5 . . . . 0.0(4) no
C7 C1 C6 C5 . . . . -178.0(2) no
C2 C1 C7 O1 . . . . -170.1(2) no
C2 C1 C7 N1 . . . . 8.6(3) no
C6 C1 C7 O1 . . . . 7.7(4) no
C6 C1 C7 N1 . . . . -173.6(2) no
C1 C2 C3 C4 . . . . 0.7(4) no
C2 C3 C4 C5 . . . . 0.6(4) no
C3 C4 C5 C6 . . . . -1.6(4) no
C4 C5 C6 C1 . . . . 1.3(4) no
S1 C8 C9 C10 . . . . 0.33(19) no
S1 C8 C9 C16 . . . . -179.36(15) no
N1 C8 C9 C10 . . . . -179.57(16) no
N1 C8 C9 C16 . . . . 0.8(3) no
C8 C9 C10 C11 . . . . 178.53(18) no
C8 C9 C10 C15 . . . . -0.6(2) no
C16 C9 C10 C11 . . . . -1.8(3) no
C16 C9 C10 C15 . . . . 179.1(2) no
C8 C9 C16 O2 . . . . -1.6(3) no
C8 C9 C16 O3 . . . . 177.88(18) no
C10 C9 C16 O2 . . . . 178.8(2) no
C10 C9 C16 O3 . . . . -1.8(3) no
C9 C10 C11 C12A . . . . 170.4(3) no
C15 C10 C11 C12A . . . . -10.6(4) no
C9 C10 C15 S1 . . . . 0.6(2) no
C9 C10 C15 C14 . . . . 178.9(2) no
C11 C10 C15 S1 . . . . -178.60(16) no
C11 C10 C15 C14 . . . . -0.3(3) no
C10 C11 C12A C13A . . . . 39.9(5) no
C11 C12A C13A C14 . . . . -59.8(6) no
C12A C13A C14 C15 . . . . 46.7(5) no
C13A C14 C15 S1 . . . . 160.7(3) no
C13A C14 C15 C10 . . . . -17.5(4) no
