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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
diethyl 2,5-diaminothiophene-3,4-dicarboxylate
;
_chemical_name_common
;
2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester
;
_chemical_formula_moiety     'C10 H14 N2 O4 S'
_chemical_formula_sum     'C10 H14 N2 O4 S'
_chemical_formula_iupac     'C10 H14 N2 O4 S'
_chemical_formula_weight     258.29
_chemical_melting_point        .428E-305
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_hall     '-P 2ybc'
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'
_cell_length_a     9.5306(3)
_cell_length_b     8.8206(3)
_cell_length_c     15.5518(5)
_cell_angle_alpha     90.00
_cell_angle_beta     105.9630(10)
_cell_angle_gamma     90.00
_cell_volume     1256.96(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8976
_cell_measurement_theta_min     4.83
_cell_measurement_theta_max     68.26
_cell_measurement_temperature     220(2)
_exptl_crystal_description     block
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.365
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     544
_exptl_absorpt_coefficient_mu     2.368
_exptl_absorpt_correction_Type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.405
_exptl_absorpt_correction_T_max     0.702
_exptl_special_details
;
On completion of the data collection, the first
101 frames were recollected for decay correction analysis using SAINT.
;
_diffrn_ambient_temperature     220(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'Rotating Anode'
_diffrn_radiation_monochromator     'Montel 200 optics'
_diffrn_measurement_device_type     'Bruker SMART 6000'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     5.5
_diffrn_reflns_number     16465
_diffrn_reflns_av_R_equivalents     0.055
_diffrn_reflns_av_sigmaI/netI     0.0234
_diffrn_reflns_theta_min     4.83
_diffrn_reflns_theta_max     68.31
_diffrn_reflns_theta_full     68.31
_diffrn_measured_fraction_theta_max     0.980
_diffrn_measured_fraction_theta_full     0.980
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2270
_reflns_number_gt     2032
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0447
_refine_ls_R_factor_gt     0.0420
_refine_ls_wR_factor_gt     0.1225
_refine_ls_wR_factor_ref     0.1255
_refine_ls_goodness_of_fit_ref     1.071
_refine_ls_restrained_S_all     1.071
_refine_ls_number_reflns     2270
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0895P)²+0.1856P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.012
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.303
_refine_diff_density_min     -0.251
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2003)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                          'ORTEPIII (Farrugia, 1997) and SHELXTL (Bruker, 1997)'
_computing_publication_material     'UdMX (Maris, 2004)'
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_disorder_assembly
    _atom_site_disorder_group
    S S1 0.44693(5) 0.25668(5) 0.15560(3) 0.0394(2) Uani d . 1 . .
    O O1 0.03919(14) -0.04344(15) 0.10762(9) 0.0451(4) Uani d . 1 . .
    O O2 0.02651(12) 0.06675(14) 0.23561(8) 0.0357(3) Uani d . 1 . .
    O O3 0.26221(13) -0.01334(14) 0.37325(8) 0.0392(3) Uani d . 1 . .
    O O4 0.38359(14) 0.19601(16) 0.43339(8) 0.0441(3) Uani d . 1 . .
    N N1 0.23991(18) 0.1084(2) 0.03354(10) 0.0469(4) Uani d . 1 . .
    H H1A 0.1630 0.0514 0.0151 0.056 Uiso calc R 1 . .
    H H1B 0.2838 0.1433 -0.0045 0.056 Uiso calc R 1 . .
    N N2 0.54748(17) 0.3193(2) 0.33018(11) 0.0512(5) Uani d . 1 . .
    H H2A 0.5494 0.3112 0.3862 0.061 Uiso calc R 1 . .
    H H2B 0.6133 0.3732 0.3149 0.061 Uiso calc R 1 . .
    C C1 0.29108(18) 0.14254(19) 0.12110(11) 0.0335(4) Uani d . 1 . .
    C C2 0.23954(17) 0.10016(17) 0.19235(10) 0.0298(4) Uani d . 1 . .
    C C3 0.33000(17) 0.15861(18) 0.27735(10) 0.0301(4) Uani d . 1 . .
    C C4 0.44253(19) 0.24820(18) 0.26684(12) 0.0352(4) Uani d . 1 . .
    C C5 0.09533(17) 0.03121(17) 0.17386(11) 0.0307(4) Uani d . 1 . .
    C C6 0.32620(17) 0.11865(19) 0.36730(11) 0.0328(4) Uani d . 1 . .
    C C7 -0.11305(19) -0.0064(2) 0.22757(13) 0.0422(4) Uani d . 1 . .
    H H7A -0.1000 -0.1158 0.2375 0.051 Uiso calc R 1 . .
    H H7B -0.1793 0.0105 0.1679 0.051 Uiso calc R 1 . .
    C C8 -0.1728(3) 0.0632(4) 0.2970(2) 0.0794(9) Uani d . 1 . .
    H H8A -0.1117 0.0360 0.3558 0.119 Uiso calc R 1 . .
    H H8B -0.2712 0.0264 0.2900 0.119 Uiso calc R 1 . .
    H H8C -0.1745 0.1726 0.2904 0.119 Uiso calc R 1 . .
    C C9 0.2495(2) -0.0531(2) 0.46179(13) 0.0504(5) Uani d . 1 . .
    H H9A 0.1930 0.0242 0.4829 0.061 Uiso calc R 1 . .
    H H9B 0.3465 -0.0597 0.5044 0.061 Uiso calc R 1 . .
    C C10 0.1747(4) -0.2015(3) 0.45402(16) 0.0758(8) Uani d . 1 . .
    H H10A 0.0793 -0.1938 0.4112 0.114 Uiso calc R 1 . .
    H H10B 0.1633 -0.2307 0.5119 0.114 Uiso calc R 1 . .
    H H10C 0.2323 -0.2773 0.4339 0.114 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0378(3) 0.0434(3) 0.0429(3) -0.00892(16) 0.0210(2) 0.00052(16)
    O1 0.0464(7) 0.0520(8) 0.0395(7) -0.0161(6) 0.0161(6) -0.0110(6)
    O2 0.0289(6) 0.0418(7) 0.0406(7) -0.0060(5) 0.0166(5) -0.0051(5)
    O3 0.0451(7) 0.0423(7) 0.0312(6) -0.0072(5) 0.0121(5) 0.0026(5)
    O4 0.0460(7) 0.0527(8) 0.0372(7) -0.0080(6) 0.0173(5) -0.0129(6)
    N1 0.0516(9) 0.0599(10) 0.0332(8) -0.0153(8) 0.0183(6) -0.0013(7)
    N2 0.0468(10) 0.0621(11) 0.0484(10) -0.0243(8) 0.0192(7) -0.0119(8)
    C1 0.0335(8) 0.0331(8) 0.0374(9) -0.0010(6) 0.0153(6) 0.0011(6)
    C2 0.0299(8) 0.0286(8) 0.0342(8) 0.0007(6) 0.0144(6) -0.0005(6)
    C3 0.0290(8) 0.0300(8) 0.0347(9) 0.0007(6) 0.0142(6) -0.0023(6)
    C4 0.0326(9) 0.0346(9) 0.0415(10) -0.0016(6) 0.0156(7) -0.0024(6)
    C5 0.0317(8) 0.0298(8) 0.0329(8) 0.0003(6) 0.0125(6) 0.0025(6)
    C6 0.0277(8) 0.0386(9) 0.0348(9) 0.0024(6) 0.0129(6) -0.0032(7)
    C7 0.0312(9) 0.0478(10) 0.0511(11) -0.0100(8) 0.0173(7) 0.0003(8)
    C8 0.0565(14) 0.098(2) 0.105(2) -0.0267(13) 0.0574(15) -0.0374(16)
    C9 0.0601(12) 0.0584(12) 0.0341(10) -0.0131(9) 0.0152(8) 0.0050(8)
    C10 0.114(2) 0.0672(15) 0.0475(13) -0.0355(15) 0.0249(13) 0.0065(11)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 . . 1.7434(19) Y
    S1 C1 . . 1.7519(17) Y
    O1 C5 . . 1.216(2) N
    O2 C5 . . 1.3405(19) N
    O2 C7 . . 1.452(2) N
    O3 C6 . . 1.329(2) N
    O3 C9 . . 1.458(2) N
    O4 C6 . . 1.230(2) Y
    N1 C1 . . 1.348(2) Y
    N1 H1A . . 0.87 N
    N1 H1B . . 0.87 N
    N2 C4 . . 1.350(2) Y
    N2 H2A . . 0.87 N
    N2 H2B . . 0.87 N
    C1 C2 . . 1.381(2) Y
    C2 C5 . . 1.457(2) Y
    C2 C3 . . 1.459(2) Y
    C3 C4 . . 1.378(2) Y
    C3 C6 . . 1.453(2) N
    C7 C8 . . 1.485(3) N
    C7 H7A . . 0.98 N
    C7 H7B . . 0.98 N
    C8 H8A . . 0.97 N
    C8 H8B . . 0.97 N
    C8 H8C . . 0.97 N
    C9 C10 . . 1.480(3) N
    C9 H9A . . 0.98 N
    C9 H9B . . 0.98 N
    C10 H10A . . 0.97 N
    C10 H10B . . 0.97 N
    C10 H10C . . 0.97 N
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
    C4 S1 C1 . . . 91.69(8) N
    C5 O2 C7 . . . 116.83(13) N
    C6 O3 C9 . . . 115.79(14) N
    C1 N1 H1A . . . 120 N
    C1 N1 H1B . . . 120 ?
    H1A N1 H1B . . . 120 ?
    C4 N2 H2A . . . 120 ?
    C4 N2 H2B . . . 120 ?
    H2A N2 H2B . . . 120 ?
    N1 C1 C2 . . . 129.79(16) N
    N1 C1 S1 . . . 118.59(13) N
    C2 C1 S1 . . . 111.62(12) N
    C1 C2 C5 . . . 118.61(14) N
    C1 C2 C3 . . . 112.28(14) N
    C5 C2 C3 . . . 128.04(13) N
    C4 C3 C6 . . . 118.68(15) N
    C4 C3 C2 . . . 112.35(14) N
    C6 C3 C2 . . . 128.43(14) N
    N2 C4 C3 . . . 128.66(17) N
    N2 C4 S1 . . . 119.27(13) N
    C3 C4 S1 . . . 111.98(13) N
    O1 C5 O2 . . . 123.07(15) N
    O1 C5 C2 . . . 124.38(15) N
    O2 C5 C2 . . . 112.44(14) N
    O4 C6 O3 . . . 122.35(15) N
    O4 C6 C3 . . . 123.17(15) N
    O3 C6 C3 . . . 114.39(14) N
    O2 C7 C8 . . . 106.21(16) N
    O2 C7 H7A . . . 110.5 ?
    C8 C7 H7A . . . 110.5 ?
    O2 C7 H7B . . . 110.5 ?
    C8 C7 H7B . . . 110.5 ?
    H7A C7 H7B . . . 108.7 ?
    C7 C8 H8A . . . 109.5 ?
    C7 C8 H8B . . . 109.5 ?
    H8A C8 H8B . . . 109.5 ?
    C7 C8 H8C . . . 109.5 ?
    H8A C8 H8C . . . 109.5 ?
    H8B C8 H8C . . . 109.5 ?
    O3 C9 C10 . . . 107.40(17) N
    O3 C9 H9A . . . 110.2 ?
    C10 C9 H9A . . . 110.2 ?
    O3 C9 H9B . . . 110.2 ?
    C10 C9 H9B . . . 110.2 ?
    H9A C9 H9B . . . 108.5 ?
    C9 C10 H10A . . . 109.5 ?
    C9 C10 H10B . . . 109.5 ?
    H10A C10 H10B . . . 109.5 ?
    C9 C10 H10C . . . 109.5 ?
    H10A C10 H10C . . . 109.5 ?
    H10B C10 H10C . . . 109.5 ?
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
    C4 S1 C1 N1 . . . . -179.91(15) N
    C4 S1 C1 C2 . . . . -0.25(13) N
    N1 C1 C2 C5 . . . . -12.5(3) N
    S1 C1 C2 C5 . . . . 167.85(12) N
    N1 C1 C2 C3 . . . . 178.35(17) N
    S1 C1 C2 C3 . . . . -1.27(18) N
    C1 C2 C3 C4 . . . . 2.6(2) N
    C5 C2 C3 C4 . . . . -165.20(15) N
    C1 C2 C3 C6 . . . . -168.76(16) N
    C5 C2 C3 C6 . . . . 23.4(3) N
    C6 C3 C4 N2 . . . . -6.9(3) N
    C2 C3 C4 N2 . . . . -179.28(17) N
    C6 C3 C4 S1 . . . . 169.53(12) N
    C2 C3 C4 S1 . . . . -2.80(18) N
    C1 S1 C4 N2 . . . . 178.63(15) N
    C1 S1 C4 C3 . . . . 1.78(13) N
    C7 O2 C5 O1 . . . . 8.8(2) N
    C7 O2 C5 C2 . . . . -175.00(14) N
    C1 C2 C5 O1 . . . . 29.2(2) N
    C3 C2 C5 O1 . . . . -163.64(17) N
    C1 C2 C5 O2 . . . . -147.00(15) N
    C3 C2 C5 O2 . . . . 20.2(2) Y
    C9 O3 C6 O4 . . . . 6.7(2) N
    C9 O3 C6 C3 . . . . -176.82(15) N
    C4 C3 C6 O4 . . . . 25.4(2) N
    C2 C3 C6 O4 . . . . -163.69(16) N
    C4 C3 C6 O3 . . . . -151.10(15) N
    C2 C3 C6 O3 . . . . 19.8(2) Y
    C5 O2 C7 C8 . . . . -174.27(19) N
    C6 O3 C9 C10 . . . . 179.40(19) 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
    N1 H1A O1 . 0.87 2.26 2.827(2) 123
    N1 H1A O1 3 0.87 2.31 3.002(2) 137
    N1 H1B O4 4_565 0.87 2.09 2.907(2) 157
    N2 H2A O4 . 0.87 2.17 2.753(2) 124
data_global
_journal_date_recd_electronic     2006-09-28
_journal_date_accepted     2006-11-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     12
_journal_page_first     o5529
_journal_page_last     o5531
_journal_paper_category     EO
_journal_coeditor_code     GA2015
_publ_contact_author_name     'W. G. Skene'
_publ_contact_author_address
;
Department of Chemistry
University of Montreal
CP 6128
Succ. Centre-ville
Montreal
Quebec
Canada H3C 3J7
;
_publ_contact_author_email     'w.skene@umontreal.ca'
_publ_contact_author_fax     '(514) 340-5290'
_publ_contact_author_phone     '(514) 340-5174'
_publ_section_title
;
Hydrogen-bonded network of diethyl 2,5-diaminothiophene-3,4-dicarboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Bourgeaux, Marie' .
;
Department of Chemistry
University of Montreal
CP 6128, Succ. Centre-ville
Montreal
Quebec
Canada H3C 3J7
;
    'Vomsheid, Sophie' .
;
Institut Universitaire Technologique
Paul Sabatier de Castres Université de Toulouse III
Toulouse
France
;
    'Skene, W. G.' .
;
Department of Chemistry
University of Montreal
CP 6128, Succ. Centre-ville
Montreal
Quebec
Canada H3C 3J7
;
