#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/00/2210069.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_2210069
loop_
_publ_author_name
'Döpp, Dietrich'
'Sopbue Fondjo, Emmanuel'
'Flörke, Ulrich'
'Henkel, Gerald'
_publ_section_title
;Dimethyl
 2-(3-amino-4-oxo-4H-benzo[f]thieno[3,4-c]chromen-1-yl)fumarate
;
_journal_coeditor_code           AT2089
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4095
_journal_page_last               o4097
_journal_paper_doi               10.1107/S1600536806033460
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H15 N O6 S'
_chemical_formula_moiety         'C21 H15 N O6 S'
_chemical_formula_sum            'C21 H15 N O6 S'
_chemical_formula_weight         409.40
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.400(10)
_cell_angle_beta                 91.500(10)
_cell_angle_gamma                93.710(10)
_cell_formula_units_Z            2
_cell_length_a                   7.718(8)
_cell_length_b                   9.451(11)
_cell_length_c                   13.058(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      10
_cell_volume                     895.4(17)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4 rotating anode'
_diffrn_measurement_method       'ω scans'
_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  0.0129
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3903
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.9025
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.311
_refine_ls_extinction_coef       0.0040(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0390
_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)+(0.0446P)²+0.3857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                3223
_reflns_number_total             3901
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2089.cif
_cod_data_source_block           IV
_cod_database_code               2210069
_cod_database_fobs_code          2210069
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.53326(6) 0.10970(5) 0.41208(4) 0.02568(13) Uani d . 1
O O1 0.82022(16) 0.56706(14) 0.45136(11) 0.0275(3) Uani d . 1
O O2 0.61075(16) 0.58530(14) 0.33870(11) 0.0261(3) Uani d . 1
O O3 0.20242(18) -0.05197(16) 0.40425(11) 0.0331(3) Uani d . 1
O O4 -0.00232(17) -0.09279(16) 0.27166(11) 0.0324(3) Uani d . 1
O O5 0.47797(16) 0.13734(15) 0.10230(10) 0.0297(3) Uani d . 1
O O6 0.22100(17) 0.10322(16) 0.00914(11) 0.0325(3) Uani d . 1
N N1 0.81636(19) 0.29392(18) 0.49989(13) 0.0277(4) Uani d . 1
H H1A 0.8517 0.2202 0.5229 0.033 Uiso d R 1
H H1B 0.8831 0.3808 0.5151 0.033 Uiso d R 1
C C1 0.1719(2) 0.39492(19) 0.24165(14) 0.0213(3) Uani d . 1
C C2 0.0397(2) 0.2968(2) 0.26154(14) 0.0232(4) Uani d . 1
H H2A 0.0633 0.2475 0.3133 0.028 Uiso d R 1
C C3 -0.1211(2) 0.2723(2) 0.20849(15) 0.0267(4) Uani d . 1
H H3A -0.2060 0.2010 0.2200 0.032 Uiso d R 1
C C4 -0.1630(2) 0.3500(2) 0.13746(16) 0.0304(4) Uani d . 1
H H4A -0.2734 0.3281 0.0976 0.036 Uiso d R 1
C C5 -0.0449(2) 0.4562(2) 0.12487(16) 0.0302(4) Uani d . 1
H H5A -0.0762 0.5147 0.0805 0.036 Uiso d R 1
C C6 0.1235(2) 0.4827(2) 0.17693(15) 0.0247(4) Uani d . 1
C C7 0.2429(2) 0.5990(2) 0.16878(17) 0.0309(4) Uani d . 1
H H7A 0.2129 0.6557 0.1229 0.037 Uiso d R 1
C C8 0.3992(2) 0.6297(2) 0.22495(17) 0.0302(4) Uani d . 1
H H8A 0.4756 0.7137 0.2246 0.036 Uiso d R 1
C C9 0.4494(2) 0.5385(2) 0.28478(15) 0.0238(4) Uani d . 1
C C10 0.3478(2) 0.41345(19) 0.28791(14) 0.0204(3) Uani d . 1
C C11 0.4300(2) 0.31418(19) 0.33687(13) 0.0192(3) Uani d . 1
C C12 0.3861(2) 0.16771(19) 0.33178(14) 0.0212(3) Uani d . 1
C C13 0.2576(2) 0.05091(19) 0.26326(15) 0.0223(4) Uani d . 1
C C14 0.2255(2) 0.0203(2) 0.15624(15) 0.0241(4) Uani d . 1
H H14A 0.1327 -0.0538 0.1206 0.029 Uiso d R 1
C C15 0.3264(2) 0.09391(19) 0.08946(14) 0.0233(4) Uani d . 1
C C16 0.6831(2) 0.51131(19) 0.40212(14) 0.0217(4) Uani d . 1
C C17 0.5911(2) 0.37359(19) 0.39885(13) 0.0200(3) Uani d . 1
C C18 0.6646(2) 0.2742(2) 0.44267(14) 0.0219(4) Uani d . 1
C C19 0.1522(2) -0.0370(2) 0.32095(15) 0.0238(4) Uani d . 1
C C20 -0.1095(2) -0.1767(2) 0.32530(17) 0.0347(5) Uani d . 1
H H20C -0.0586 -0.2686 0.3203 0.052 Uiso d R 1
H H20A -0.2243 -0.1986 0.2912 0.052 Uiso d R 1
H H20B -0.1187 -0.1172 0.4002 0.052 Uiso d R 1
C C21 0.3009(3) 0.1774(3) -0.05962(18) 0.0437(6) Uani d . 1
H H21C 0.2117 0.2058 -0.1000 0.066 Uiso d R 1
H H21A 0.3725 0.1109 -0.1099 0.066 Uiso d R 1
H H21B 0.3713 0.2662 -0.0173 0.066 Uiso d 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 0.0033 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
_geom_angle_publ_flag
C18 S1 C12 92.48(10) y
C16 O2 C9 122.10(14) y
C19 O4 C20 115.25(15) ?
C15 O6 C21 114.64(16) ?
C18 N1 H1A 120.0 ?
C18 N1 H1B 120.0 ?
H1A N1 H1B 120.0 ?
C2 C1 C6 117.26(17) ?
C2 C1 C10 122.97(16) ?
C6 C1 C10 119.71(16) ?
C3 C2 C1 121.08(17) ?
C3 C2 H2A 119.6 ?
C1 C2 H2A 119.3 ?
C2 C3 C4 120.91(17) ?
C2 C3 H3A 119.6 ?
C4 C3 H3A 119.5 ?
C5 C4 C3 119.43(18) ?
C5 C4 H4A 120.2 ?
C3 C4 H4A 120.4 ?
C4 C5 C6 121.13(18) ?
C4 C5 H5A 119.7 ?
C6 C5 H5A 119.2 ?
C5 C6 C7 121.09(17) ?
C5 C6 C1 119.55(17) ?
C7 C6 C1 119.32(17) ?
C8 C7 C6 120.41(17) ?
C8 C7 H7A 119.9 ?
C6 C7 H7A 119.7 ?
C7 C8 C9 119.94(17) ?
C7 C8 H8A 120.5 ?
C9 C8 H8A 119.6 ?
O2 C9 C10 123.78(16) ?
O2 C9 C8 113.10(16) ?
C10 C9 C8 123.12(17) ?
C9 C10 C1 116.23(16) ?
C9 C10 C11 116.75(17) ?
C1 C10 C11 127.02(15) ?
C12 C11 C17 111.66(15) ?
C12 C11 C10 132.10(16) ?
C17 C11 C10 116.18(16) ?
C11 C12 C13 132.21(16) ?
C11 C12 S1 111.11(13) ?
C13 C12 S1 116.15(14) ?
C14 C13 C12 125.26(16) ?
C14 C13 C19 118.84(16) ?
C12 C13 C19 115.88(16) ?
C13 C14 C15 123.80(16) ?
C13 C14 H14A 118.1 ?
C15 C14 H14A 118.1 ?
O5 C15 O6 124.07(17) ?
O5 C15 C14 127.08(17) ?
O6 C15 C14 108.84(16) ?
O1 C16 O2 116.81(16) ?
O1 C16 C17 127.29(16) ?
O2 C16 C17 115.84(16) ?
C18 C17 C16 121.67(17) ?
C18 C17 C11 113.88(16) ?
C16 C17 C11 123.77(15) ?
N1 C18 C17 128.04(16) ?
N1 C18 S1 121.37(14) ?
C17 C18 S1 110.59(14) ?
O3 C19 O4 123.66(16) ?
O3 C19 C13 122.97(16) ?
O4 C19 C13 113.35(16) ?
O4 C20 H20C 109.6 ?
O4 C20 H20A 109.5 ?
H20C C20 H20A 109.9 ?
O4 C20 H20B 109.9 ?
H20C C20 H20B 109.9 ?
H20A C20 H20B 108.1 ?
O6 C21 H21C 109.1 ?
O6 C21 H21A 110.2 ?
H21C C21 H21A 108.8 ?
O6 C21 H21B 111.0 ?
H21C C21 H21B 108.8 ?
H21A C21 H21B 108.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C18 1.723(2) y
S1 C12 1.758(2) y
O1 C16 1.216(2) y
O2 C16 1.377(2) y
O2 C9 1.385(2) y
O3 C19 1.200(2) ?
O4 C19 1.330(2) ?
O4 C20 1.455(2) ?
O5 C15 1.203(2) ?
O6 C15 1.340(2) ?
O6 C21 1.439(2) ?
N1 C18 1.341(2) y
N1 H1A 0.9000 ?
N1 H1B 0.9000 ?
C1 C2 1.421(3) y
C1 C6 1.425(3) y
C1 C10 1.447(3) y
C2 C3 1.373(3) y
C2 H2A 0.9601 ?
C3 C4 1.404(3) y
C3 H3A 0.9600 ?
C4 C5 1.366(3) y
C4 H4A 0.9600 ?
C5 C6 1.419(3) y
C5 H5A 0.9600 ?
C6 C7 1.421(3) y
C7 C8 1.358(3) y
C7 H7A 0.9600 ?
C8 C9 1.406(3) y
C8 H8A 0.9600 ?
C9 C10 1.388(3) y
C10 C11 1.465(3) y
C11 C12 1.383(3) y
C11 C17 1.439(2) y
C12 C13 1.469(2) y
C13 C14 1.342(3) y
C13 C19 1.510(2) y
C14 C15 1.490(3) ?
C14 H14A 0.9600 ?
C16 C17 1.429(3) y
C17 C18 1.393(3) y
C20 H20C 0.9600 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C21 H21C 0.9600 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
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
C14 H14A O4 . 0.96 2.38 2.733(3) 101.3
N1 H1B O1 . 0.90 2.26 2.854(4) 123.6
N1 H1A O3 2_656 0.90 2.13 2.947(3) 150.2
N1 H1B O1 2_766 0.90 2.31 2.979(3) 130.9
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
C6 C1 C2 C3 8.8(3)
C10 C1 C2 C3 -174.13(17)
C1 C2 C3 C4 -3.6(3)
C2 C3 C4 C5 -3.0(3)
C3 C4 C5 C6 4.1(3)
C4 C5 C6 C7 -176.40(19)
C4 C5 C6 C1 1.4(3)
C2 C1 C6 C5 -7.6(3)
C10 C1 C6 C5 175.20(16)
C2 C1 C6 C7 170.21(17)
C10 C1 C6 C7 -7.0(3)
C5 C6 C7 C8 175.54(19)
C1 C6 C7 C8 -2.2(3)
C6 C7 C8 C9 5.1(3)
C16 O2 C9 C10 -1.0(3)
C16 O2 C9 C8 179.75(16)
C7 C8 C9 O2 -179.17(17)
C7 C8 C9 C10 1.6(3)
O2 C9 C10 C1 170.38(16)
C8 C9 C10 C1 -10.5(3)
O2 C9 C10 C11 -10.0(3)
C8 C9 C10 C11 169.16(17)
C2 C1 C10 C9 -164.10(17)
C6 C1 C10 C9 12.9(2)
C2 C1 C10 C11 16.3(3)
C6 C1 C10 C11 -166.66(17)
C9 C10 C11 C12 -162.82(19)
C1 C10 C11 C12 16.8(3)
C9 C10 C11 C17 14.0(2)
C1 C10 C11 C17 -166.35(16)
C17 C11 C12 C13 -166.29(18)
C10 C11 C12 C13 10.7(3)
C17 C11 C12 S1 4.81(19)
C10 C11 C12 S1 -178.22(15)
C18 S1 C12 C11 -5.13(14)
C18 S1 C12 C13 167.53(14)
C11 C12 C13 C14 42.1(3)
S1 C12 C13 C14 -128.67(18)
C11 C12 C13 C19 -136.3(2)
S1 C12 C13 C19 53.0(2)
C12 C13 C14 C15 4.8(3)
C19 C13 C14 C15 -176.86(16)
C21 O6 C15 O5 -3.0(3)
C21 O6 C15 C14 177.85(17)
C13 C14 C15 O5 32.2(3)
C13 C14 C15 O6 -148.66(18)
C9 O2 C16 O1 -175.50(16)
C9 O2 C16 C17 7.0(2)
O1 C16 C17 C18 -9.0(3)
O2 C16 C17 C18 168.15(16)
O1 C16 C17 C11 -179.00(17)
O2 C16 C17 C11 -1.8(3)
C12 C11 C17 C18 -1.9(2)
C10 C11 C17 C18 -179.37(15)
C12 C11 C17 C16 168.79(16)
C10 C11 C17 C16 -8.7(2)
C16 C17 C18 N1 6.1(3)
C11 C17 C18 N1 176.97(17)
C16 C17 C18 S1 -172.89(13)
C11 C17 C18 S1 -2.0(2)
C12 S1 C18 N1 -175.06(16)
C12 S1 C18 C17 4.00(14)
C20 O4 C19 O3 -0.6(3)
C20 O4 C19 C13 -179.18(16)
C14 C13 C19 O3 156.66(19)
C12 C13 C19 O3 -24.9(3)
C14 C13 C19 O4 -24.8(2)
C12 C13 C19 O4 153.69(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21178871
