#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/81/2238102.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_2238102
loop_
_publ_author_name
'Li, Xiuping'
'Jia, Xiaochuan'
'Li, Jing'
_publ_section_title
;
 Ethyl
 3-bromo-4-cyano-5-[(2-ethoxy-2-oxoethyl)sulfanyl]thiophene-2-carboxylate
;
_journal_coeditor_code           ZJ2102
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o848
_journal_paper_doi               10.1107/S1600536813010611
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H12 Br N O4 S2'
_chemical_formula_moiety         'C12 H12 Br N O4 S2'
_chemical_formula_sum            'C12 H12 Br N O4 S2'
_chemical_formula_weight         378.26
_chemical_name_systematic
;
Ethyl 3-bromo-4-cyano-5-[(2-ethoxy-2-oxoethyl)sulfanyl]thiophene-2-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                90.00
_cell_angle_beta                 99.44(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5896(17)
_cell_length_b                   10.837(2)
_cell_length_c                   16.584(3)
_cell_measurement_reflns_used    3404
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8744
_cell_measurement_theta_min      3.0517
_cell_volume                     1522.8(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15211
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         3.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.984
_exptl_absorpt_correction_T_max  0.7160
_exptl_absorpt_correction_T_min  0.5868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.711
_refine_ls_extinction_coef       0.018(2)
_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   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0817P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1568
_reflns_number_gt                2224
_reflns_number_total             3596
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zj2102.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238102
_cod_database_fobs_code          2238102
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
_atom_site_symmetry_multiplicity
Br Br1 1.34684(5) -0.05401(5) 0.13435(3) 0.0723(3) Uani d . 1 1
S S1 0.95059(11) 0.19092(9) 0.04312(6) 0.0421(3) Uani d . 1 1
S S2 0.75972(12) 0.13383(10) 0.17935(7) 0.0505(3) Uani d . 1 1
O O1 1.3519(4) 0.1042(3) -0.0246(2) 0.0703(9) Uani d . 1 1
O O2 1.1477(3) 0.2261(3) -0.07630(18) 0.0577(8) Uani d . 1 1
O O3 0.4240(3) 0.3685(3) 0.10494(18) 0.0559(8) Uani d . 1 1
O O4 0.4796(4) 0.2478(3) 0.2147(2) 0.0744(10) Uani d . 1 1
N N1 1.0569(5) -0.0869(4) 0.2904(3) 0.0784(13) Uani d . 1 1
C C1 1.3411(7) 0.3617(5) -0.1215(3) 0.0825(16) Uani d . 1 1
H H1A 1.2890 0.4277 -0.0980 0.124 Uiso calc R 1 1
H H1B 1.3794 0.3912 -0.1692 0.124 Uiso calc R 1 1
H H1C 1.4282 0.3325 -0.0823 0.124 Uiso calc R 1 1
C C2 1.2285(6) 0.2598(5) -0.1446(3) 0.0667(13) Uani d . 1 1
H H2A 1.1510 0.2847 -0.1911 0.080 Uiso calc R 1 1
H H2B 1.2845 0.1885 -0.1607 0.080 Uiso calc R 1 1
C C3 1.2245(5) 0.1481(4) -0.0215(3) 0.0468(10) Uani d . 1 1
C C4 1.1325(4) 0.1209(3) 0.0445(2) 0.0420(9) Uani d . 1 1
C C5 1.1667(5) 0.0433(3) 0.1088(3) 0.0440(9) Uani d . 1 1
C C6 1.0474(4) 0.0400(3) 0.1587(2) 0.0427(9) Uani d . 1 1
C C7 0.9215(4) 0.1161(3) 0.1300(2) 0.0390(8) Uani d . 1 1
C C8 1.0542(5) -0.0323(4) 0.2309(3) 0.0551(11) Uani d . 1 1
C C9 0.6413(4) 0.2381(4) 0.1105(2) 0.0473(10) Uani d . 1 1
H H9A 0.7050 0.3072 0.0979 0.057 Uiso calc R 1 1
H H9B 0.6003 0.1960 0.0599 0.057 Uiso calc R 1 1
C C10 0.5069(4) 0.2838(4) 0.1508(3) 0.0464(10) Uani d . 1 1
C C11 0.2964(6) 0.4242(5) 0.1395(3) 0.0632(13) Uani d . 1 1
H H11A 0.3373 0.4630 0.1914 0.076 Uiso calc R 1 1
H H11B 0.2205 0.3617 0.1488 0.076 Uiso calc R 1 1
C C12 0.2186(6) 0.5190(5) 0.0800(4) 0.0903(18) Uani d . 1 1
H H12A 0.2957 0.5782 0.0691 0.135 Uiso calc R 1 1
H H12B 0.1371 0.5603 0.1029 0.135 Uiso calc R 1 1
H H12C 0.1733 0.4791 0.0299 0.135 Uiso calc R 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'
Br Br -0.2901 2.4595 '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
C7 S1 C4 92.15(19)
C7 S2 C9 100.55(18)
C3 O2 C2 116.1(3)
C10 O3 C11 115.6(3)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O2 C2 C1 111.0(4)
O2 C2 H2A 109.4
C1 C2 H2A 109.4
O2 C2 H2B 109.4
C1 C2 H2B 109.4
H2A C2 H2B 108.0
O1 C3 O2 124.9(4)
O1 C3 C4 123.6(4)
O2 C3 C4 111.4(3)
C5 C4 C3 129.3(3)
C5 C4 S1 111.1(3)
C3 C4 S1 119.5(3)
C4 C5 C6 113.1(3)
C4 C5 Br1 126.6(3)
C6 C5 Br1 120.4(3)
C7 C6 C5 112.6(3)
C7 C6 C8 122.7(4)
C5 C6 C8 124.7(4)
C6 C7 S1 111.1(3)
C6 C7 S2 123.1(3)
S1 C7 S2 125.8(2)
N1 C8 C6 177.4(5)
C10 C9 S2 108.6(3)
C10 C9 H9A 110.0
S2 C9 H9A 110.0
C10 C9 H9B 110.0
S2 C9 H9B 110.0
H9A C9 H9B 108.4
O4 C10 O3 125.0(4)
O4 C10 C9 124.4(4)
O3 C10 C9 110.6(4)
O3 C11 C12 108.0(4)
O3 C11 H11A 110.1
C12 C11 H11A 110.1
O3 C11 H11B 110.1
C12 C11 H11B 110.1
H11A C11 H11B 108.4
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.864(4)
S1 C7 1.707(4)
S1 C4 1.734(4)
S2 C7 1.735(4)
S2 C9 1.798(4)
O1 C3 1.202(5)
O2 C3 1.335(5)
O2 C2 1.468(5)
O3 C10 1.323(5)
O3 C11 1.449(5)
O4 C10 1.188(5)
N1 C8 1.147(6)
C1 C2 1.477(7)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.480(6)
C4 C5 1.352(5)
C5 C6 1.418(6)
C6 C7 1.381(5)
C6 C8 1.425(6)
C9 C10 1.509(5)
C9 H9A 0.9700
C9 H9B 0.9700
C11 C12 1.504(7)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
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
C3 O2 C2 C1 -83.9(5)
C2 O2 C3 O1 -0.4(6)
C2 O2 C3 C4 179.9(3)
O1 C3 C4 C5 -2.5(7)
O2 C3 C4 C5 177.2(4)
O1 C3 C4 S1 179.4(4)
O2 C3 C4 S1 -1.0(5)
C7 S1 C4 C5 0.4(3)
C7 S1 C4 C3 178.9(3)
C3 C4 C5 C6 -178.9(4)
S1 C4 C5 C6 -0.6(4)
C3 C4 C5 Br1 0.6(6)
S1 C4 C5 Br1 178.9(2)
C4 C5 C6 C7 0.5(5)
Br1 C5 C6 C7 -179.0(3)
C4 C5 C6 C8 -179.0(4)
Br1 C5 C6 C8 1.5(5)
C5 C6 C7 S1 -0.2(4)
C8 C6 C7 S1 179.4(3)
C5 C6 C7 S2 -178.6(3)
C8 C6 C7 S2 0.9(6)
C4 S1 C7 C6 -0.1(3)
C4 S1 C7 S2 178.3(3)
C9 S2 C7 C6 -178.3(3)
C9 S2 C7 S1 3.5(3)
C7 C6 C8 N1 -36(12)
C5 C6 C8 N1 144(11)
C7 S2 C9 C10 -169.7(3)
C11 O3 C10 O4 3.5(6)
C11 O3 C10 C9 -176.8(4)
S2 C9 C10 O4 -5.4(6)
S2 C9 C10 O3 174.9(3)
C10 O3 C11 C12 178.9(4)
