#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/93/2209359.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_2209359
loop_
_publ_author_name
'Skene, W. G.'
'Dufresne, Stéphane'
'Trefz, Tyler'
_publ_section_title
;
 (E)-Diethyl
 2-amino-5-(2-thienylmethyleneamino)thiophene-3,4-dicarboxylate
;
_journal_coeditor_code           XU2038
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2382
_journal_page_last               o2384
_journal_paper_doi               10.1107/S1600536806017351
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H16 N2 O4 S2'
_chemical_formula_moiety         'C15 H16 N2 O4 S2'
_chemical_formula_sum            'C15 H16 N2 O4 S2'
_chemical_formula_weight         352.42
_chemical_melting_point          .145E-144
_chemical_name_systematic
;
(E)-Diethyl 2-amino-5-(2-thienylmethyleneamino)thiophene-3,4-dicarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.28(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.428(4)
_cell_length_b                   14.907(6)
_cell_length_c                   11.671(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      15.0
_cell_volume                     1618.8(11)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'UdMX (Marris, 2004)'
_computing_data_reduction        UdMX
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and SHELXTL (Bruker, 1997)'
_computing_publication_material  UdMX
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.0
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_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  0.062
_diffrn_reflns_av_sigmaI/netI    0.036
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            32753
_diffrn_reflns_theta_full        70.0
_diffrn_reflns_theta_max         70.0
_diffrn_reflns_theta_min         4.8
_diffrn_standards_decay_%        1.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    3.178
_exptl_absorpt_correction_T_max  0.580
_exptl_absorpt_correction_T_min  0.220
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.24
_refine_ls_extinction_coef       0.0045(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_gt           0.037
_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)+(0.0539P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.094
_refine_ls_wR_factor_ref         0.098
_reflns_number_gt                2255
_reflns_number_total             3071
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2038.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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 (19
times).

'_geom_angle_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 (32
times).

'_geom_torsion_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 (38
times).

'_geom_torsion_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 (4 times).

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

The following automatic conversions were performed:

'_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 (19
times).

'_geom_angle_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 (32
times).

'_geom_torsion_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 (38
times).

'_geom_torsion_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 (4 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2209359
_cod_database_fobs_code          2209359
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.14461(6) 0.49009(3) 0.12892(5) 0.05936(17) Uani d . 1
S S2 0.53755(6) 0.33765(4) -0.13414(6) 0.0728(2) Uani d . 1
O O1 0.11736(18) 0.41246(10) 0.50069(14) 0.0713(4) Uani d . 1
O O2 0.27441(14) 0.30405(9) 0.47569(12) 0.0560(4) Uani d . 1
O O3 0.40647(17) 0.22122(9) 0.25292(14) 0.0716(5) Uani d . 1
O O4 0.52193(14) 0.33673(9) 0.34915(13) 0.0603(4) Uani d . 1
N N1 0.02146(19) 0.52321(12) 0.31270(17) 0.0692(5) Uani d . 1
H H1A 0.0048 0.5136 0.3820 0.083 Uiso calc R 1
H H1B -0.0248 0.5645 0.2708 0.083 Uiso calc R 1
N N2 0.35443(18) 0.38644(11) 0.05243(15) 0.0552(4) Uani d . 1
C C1 0.1203(2) 0.47345(13) 0.26976(19) 0.0538(5) Uani d . 1
C C2 0.2058(2) 0.40403(12) 0.32357(18) 0.0507(5) Uani d . 1
C C3 0.2954(2) 0.36651(12) 0.24694(18) 0.0500(5) Uani d . 1
C C4 0.2758(2) 0.40471(13) 0.13977(19) 0.0534(5) Uani d . 1
C C5 0.3316(2) 0.43201(13) -0.0420(2) 0.0597(5) Uani d . 1
H H5 0.2609 0.4761 -0.0495 0.072 Uiso calc R 1
C C6 0.4087(2) 0.41874(13) -0.13614(19) 0.0558(5) Uani d . 1
C C7 0.3979(3) 0.46933(15) -0.2358(2) 0.0645(6) Uani d . 1
H H7 0.3340 0.5168 -0.2531 0.077 Uiso calc R 1
C C8 0.4947(3) 0.44109(15) -0.3088(2) 0.0687(6) Uani d . 1
H H8 0.5017 0.4678 -0.3797 0.082 Uiso calc R 1
C C9 0.5758(2) 0.37131(17) -0.2645(2) 0.0701(6) Uani d . 1
H H9 0.6453 0.3445 -0.3014 0.084 Uiso calc R 1
C C10 0.1940(2) 0.37624(13) 0.44012(19) 0.0548(5) Uani d . 1
C C11 0.2566(3) 0.26728(14) 0.58779(19) 0.0629(6) Uani d . 1
H H11A 0.1573 0.2502 0.5875 0.075 Uiso calc R 1
H H11B 0.2835 0.3114 0.6485 0.075 Uiso calc R 1
C C12 0.3527(3) 0.18666(15) 0.6081(2) 0.0784(7) Uani d . 1
H H12A 0.3287 0.1452 0.5450 0.118 Uiso calc R 1
H H12B 0.3398 0.1582 0.6795 0.118 Uiso calc R 1
H H12C 0.4511 0.2050 0.6128 0.118 Uiso calc R 1
C C13 0.4113(2) 0.29888(13) 0.28262(18) 0.0531(5) Uani d . 1
C C14 0.6400(2) 0.27872(15) 0.3981(2) 0.0697(6) Uani d . 1
H H14A 0.6738 0.2446 0.3370 0.084 Uiso calc R 1
H H14B 0.6087 0.2370 0.4527 0.084 Uiso calc R 1
C C15 0.7572(3) 0.33697(17) 0.4583(2) 0.0796(7) Uani d . 1
H H15A 0.7974 0.3714 0.4018 0.119 Uiso calc R 1
H H15B 0.8307 0.3003 0.5014 0.119 Uiso calc R 1
H H15C 0.7190 0.3768 0.5103 0.119 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
C1 S1 C4 91.58(10) n
C9 S2 C6 91.84(12) n
C10 O2 C11 116.07(16) n
C13 O4 C14 117.33(16) n
C1 N1 H1A 120 ?
C1 N1 H1B 120 ?
H1A N1 H1B 120 ?
C5 N2 C4 119.61(19) n
N1 C1 C2 128.6(2) n
N1 C1 S1 118.95(16) n
C2 C1 S1 112.42(16) n
C1 C2 C3 111.26(19) n
C1 C2 C10 120.66(18) n
C3 C2 C10 128.04(18) n
C4 C3 C2 113.75(18) n
C4 C3 C13 121.55(18) n
C2 C3 C13 124.39(18) n
C3 C4 N2 125.96(18) n
C3 C4 S1 110.96(16) n
N2 C4 S1 122.87(15) n
N2 C5 C6 123.5(2) n
N2 C5 H5 118.2 ?
C6 C5 H5 118.2 ?
C7 C6 C5 126.7(2) n
C7 C6 S2 110.74(17) n
C5 C6 S2 122.46(16) n
C6 C7 C8 112.3(2) n
C6 C7 H7 123.8 ?
C8 C7 H7 123.8 ?
C9 C8 C7 112.5(2) n
C9 C8 H8 123.7 ?
C7 C8 H8 123.7 ?
C8 C9 S2 112.55(19) n
C8 C9 H9 123.7 ?
S2 C9 H9 123.7 ?
O1 C10 O2 122.3(2) n
O1 C10 C2 124.31(19) n
O2 C10 C2 113.34(18) n
O2 C11 C12 106.87(18) n
O2 C11 H11A 110.3 ?
C12 C11 H11A 110.3 ?
O2 C11 H11B 110.3 ?
C12 C11 H11B 110.3 ?
H11A C11 H11B 108.6 ?
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 ?
O3 C13 O4 124.57(19) n
O3 C13 C3 125.1(2) n
O4 C13 C3 110.34(16) n
O4 C14 C15 107.56(18) n
O4 C14 H14A 110.2 ?
C15 C14 H14A 110.2 ?
O4 C14 H14B 110.2 ?
C15 C14 H14B 110.2 ?
H14A C14 H14B 108.5 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.714(2) n
S1 C4 1.765(2) n
S2 C9 1.696(2) n
S2 C6 1.711(2) n
O1 C10 1.216(2) n
O2 C10 1.343(2) n
O2 C11 1.453(2) n
O3 C13 1.207(2) n
O4 C13 1.322(2) n
O4 C14 1.452(2) n
N1 C1 1.349(3) y
N1 H1a 0.86 ?
N1 H1b 0.86 ?
N2 C4 1.381(3) y
N2 C5 1.283(3) y
C1 C2 1.397(3) n
C2 C3 1.439(3) n
C2 C10 1.443(3) n
C3 C4 1.359(3) n
C3 C13 1.496(3) n
C5 C6 1.426(3) y
C5 H5 0.93 ?
C6 C7 1.376(3) n
C7 C8 1.409(3) n
C7 H7 0.93 ?
C8 C9 1.344(3) n
C8 H8 0.93 ?
C9 H9 0.93 ?
C11 C12 1.501(3) n
C11 H11a 0.97 ?
C11 H11b 0.97 ?
C12 H12a 0.96 ?
C12 H12b 0.96 ?
C12 H12c 0.96 ?
C14 C15 1.489(3) n
C14 H14a 0.97 ?
C14 H14b 0.97 ?
C15 H15a 0.96 ?
C15 H15b 0.96 ?
C15 H15c 0.96 ?
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
N1 H1A O1 . 0.86 2.20 2.778(3) 124
N1 H1A O1 3_566 0.86 2.22 2.880(3) 134
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
C4 S1 C1 N1 -178.58(17) n
C4 S1 C1 C2 -1.40(16) n
N1 C1 C2 C3 178.6(2) n
S1 C1 C2 C3 1.8(2) n
N1 C1 C2 C10 0.6(3) n
S1 C1 C2 C10 -176.20(15) n
C1 C2 C3 C4 -1.3(2) n
C10 C2 C3 C4 176.50(19) n
C1 C2 C3 C13 172.40(18) n
C10 C2 C3 C13 -9.8(3) n
C2 C3 C4 N2 174.96(17) n
C13 C3 C4 N2 1.1(3) n
C2 C3 C4 S1 0.2(2) n
C13 C3 C4 S1 -173.65(14) n
C5 N2 C4 C3 -175.0(2) n
C5 N2 C4 S1 -0.9(3) y
C1 S1 C4 C3 0.65(16) y
C1 S1 C4 N2 -174.26(17) n
C4 N2 C5 C6 179.13(18) y
N2 C5 C6 C7 -174.6(2) y
N2 C5 C6 S2 1.9(3) n
C9 S2 C6 C7 0.03(18) n
C9 S2 C6 C5 -176.97(18) n
C5 C6 C7 C8 176.9(2) n
S2 C6 C7 C8 0.0(2) n
C6 C7 C8 C9 -0.1(3) n
C7 C8 C9 S2 0.1(3) n
C6 S2 C9 C8 -0.10(19) n
C11 O2 C10 O1 4.4(3) n
C11 O2 C10 C2 -174.14(16) n
C1 C2 C10 O1 -3.8(3) n
C3 C2 C10 O1 178.6(2) n
C1 C2 C10 O2 174.73(17) n
C3 C2 C10 O2 -2.9(3) n
C10 O2 C11 C12 178.54(17) n
C14 O4 C13 O3 -5.8(3) n
C14 O4 C13 C3 175.80(17) n
C4 C3 C13 O3 -77.1(3) n
C2 C3 C13 O3 109.7(3) n
C4 C3 C13 O4 101.3(2) n
C2 C3 C13 O4 -71.9(2) n
C13 O4 C14 C15 174.00(19) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654979
