#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/98/2229826.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_2229826
loop_
_publ_author_name
'Helliwell, Madeleine'
'Nasiopoulou, Despina A.'
'Harris, Philip A.'
'Kotali, Antigoni'
'Joule, John A.'
_publ_section_title
;
 N'-[1-(2,4-Dioxo-3,4-dihydro-2H-1-benzopyran-3-ylidene)ethyl]thiophene-2-carbohydrazide
;
_journal_coeditor_code           RZ2570
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1014
_journal_paper_doi               10.1107/S1600536811010907
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H12 N2 O4 S'
_chemical_formula_moiety         'C16 H12 N2 O4 S'
_chemical_formula_sum            'C16 H12 N2 O4 S'
_chemical_formula_weight         328.34
_chemical_melting_point_gt       501
_chemical_melting_point_lt       501.5
_chemical_name_systematic
;
N'-[1-(2,4-Dioxo-3,4-dihydro-2H-1-benzopyran-3-
ylidene)ethyl]thiophene-2-carbohydrazide
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                107.106(5)
_cell_angle_beta                 100.376(4)
_cell_angle_gamma                97.553(4)
_cell_formula_units_Z            2
_cell_length_a                   4.8631(11)
_cell_length_b                   11.833(3)
_cell_length_c                   13.296(3)
_cell_measurement_reflns_used    557
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.06
_cell_measurement_theta_min      3.30
_cell_volume                     705.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker,  2001)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'phi and omega 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  0.0722
_diffrn_reflns_av_sigmaI/netI    0.1401
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3526
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.364
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2441
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.875
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0579
_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)+(0.0273P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                1403
_reflns_number_total             2441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            rz2570.cif
_cod_data_source_block           I
_cod_database_code               2229826
_cod_database_fobs_code          2229826
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.0444(2) 0.21501(11) 0.90847(9) 0.0263(3) Uani d . 1 . .
O O1 -0.1997(5) 0.2309(2) 0.68338(19) 0.0196(7) Uani d . 1 . .
O O2 -0.0262(5) 0.2667(2) 0.1854(2) 0.0191(7) Uani d . 1 . .
O O3 0.2600(5) 0.1509(2) 0.2281(2) 0.0199(7) Uani d . 1 . .
O O4 -0.2081(5) 0.3697(2) 0.4843(2) 0.0189(7) Uani d . 1 . .
N N1 0.1959(7) 0.1917(3) 0.6226(3) 0.0173(8) Uani d . 1 . .
H H1N 0.391(9) 0.201(4) 0.640(3) 0.047(15) Uiso d . 1 . .
N N2 0.0996(7) 0.2368(3) 0.5397(3) 0.0150(8) Uani d . 1 . .
H H2N -0.014(9) 0.302(4) 0.552(3) 0.048(15) Uiso d . 1 . .
C C1 0.2359(8) 0.1294(4) 0.9644(3) 0.0252(11) Uani d . 1 . .
H H1 0.2486 0.1294 1.0365 0.030 Uiso calc R 1 . .
C C2 0.3682(8) 0.0614(4) 0.8950(3) 0.0262(11) Uani d . 1 . .
H H2 0.4810 0.0070 0.9124 0.031 Uiso calc R 1 . .
C C3 0.3201(8) 0.0801(4) 0.7933(3) 0.0208(10) Uani d . 1 . .
H H3 0.3987 0.0407 0.7351 0.025 Uiso calc R 1 . .
C C4 0.1463(8) 0.1620(4) 0.7887(3) 0.0147(10) Uani d . 1 . .
C C5 0.0318(8) 0.1993(3) 0.6974(3) 0.0125(9) Uani d . 1 . .
C C6 0.1535(8) 0.1983(4) 0.4433(3) 0.0133(9) Uani d U 1 . .
C C7 0.3201(8) 0.1004(4) 0.4210(3) 0.0193(10) Uani d . 1 . .
H H7A 0.5221 0.1358 0.4335 0.029 Uiso calc R 1 . .
H H7B 0.2502 0.0480 0.3456 0.029 Uiso calc R 1 . .
H H7C 0.2976 0.0528 0.4692 0.029 Uiso calc R 1 . .
C C8 0.0388(8) 0.2517(4) 0.3664(3) 0.0141(9) Uani d . 1 . .
C C9 0.1028(8) 0.2193(4) 0.2600(3) 0.0155(10) Uani d . 1 . .
C C10 -0.1924(8) 0.3525(4) 0.2107(3) 0.0176(10) Uani d . 1 . .
C C11 -0.2969(8) 0.3977(4) 0.1301(3) 0.0221(11) Uani d . 1 . .
H H11 -0.2520 0.3710 0.0614 0.027 Uiso calc R 1 . .
C C12 -0.4677(8) 0.4821(4) 0.1510(3) 0.0249(11) Uani d . 1 . .
H H12 -0.5401 0.5138 0.0960 0.030 Uiso calc R 1 . .
C C13 -0.5364(8) 0.5220(4) 0.2519(3) 0.0211(10) Uani d . 1 . .
H H13 -0.6553 0.5797 0.2656 0.025 Uiso calc R 1 . .
C C14 -0.4275(8) 0.4756(4) 0.3307(3) 0.0172(10) Uani d . 1 . .
H H14 -0.4735 0.5015 0.3993 0.021 Uiso calc R 1 . .
C C15 -0.2522(8) 0.3918(4) 0.3123(3) 0.0162(10) Uani d . 1 . .
C C16 -0.1403(8) 0.3385(4) 0.3938(3) 0.0153(10) Uani d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C4 . . 91.6(2) ?
C9 O2 C10 . . 122.5(3) ?
C5 N1 N2 . . 115.1(3) ?
C5 N1 H1N . . 123(3) ?
N2 N1 H1N . . 113(3) ?
C6 N2 N1 . . 123.0(4) ?
C6 N2 H2N . . 117(2) ?
N1 N2 H2N . . 120(2) ?
C2 C1 S1 . . 112.6(3) ?
C2 C1 H1 . . 123.7 ?
S1 C1 H1 . . 123.7 ?
C1 C2 C3 . . 112.5(4) ?
C1 C2 H2 . . 123.7 ?
C3 C2 H2 . . 123.7 ?
C4 C3 C2 . . 112.0(4) ?
C4 C3 H3 . . 124.0 ?
C2 C3 H3 . . 124.0 ?
C3 C4 C5 . . 128.9(4) ?
C3 C4 S1 . . 111.3(3) ?
C5 C4 S1 . . 119.6(3) ?
O1 C5 N1 . . 121.0(3) ?
O1 C5 C4 . . 124.1(3) ?
N1 C5 C4 . . 114.9(3) ?
N2 C6 C8 . . 116.7(4) ?
N2 C6 C7 . . 118.5(4) ?
C8 C6 C7 . . 124.7(4) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C6 C8 C16 . . 120.1(3) ?
C6 C8 C9 . . 120.1(4) ?
C16 C8 C9 . . 119.8(4) ?
O3 C9 O2 . . 115.1(3) ?
O3 C9 C8 . . 126.4(4) ?
O2 C9 C8 . . 118.5(4) ?
C11 C10 O2 . . 116.8(4) ?
C11 C10 C15 . . 121.3(4) ?
O2 C10 C15 . . 121.9(4) ?
C12 C11 C10 . . 118.9(4) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C11 C12 C13 . . 121.2(4) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C14 C13 C12 . . 118.4(4) ?
C14 C13 H13 . . 120.8 ?
C12 C13 H13 . . 120.8 ?
C13 C14 C15 . . 121.5(4) ?
C13 C14 H14 . . 119.2 ?
C15 C14 H14 . . 119.2 ?
C14 C15 C10 . . 118.6(4) ?
C14 C15 C16 . . 122.5(4) ?
C10 C15 C16 . . 118.8(4) ?
O4 C16 C8 . . 123.1(4) ?
O4 C16 C15 . . 118.6(4) ?
C8 C16 C15 . . 118.2(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.699(4) ?
S1 C4 . 1.718(4) ?
O1 C5 . 1.232(4) ?
O2 C9 . 1.374(4) ?
O2 C10 . 1.382(5) ?
O3 C9 . 1.223(4) ?
O4 C16 . 1.268(4) ?
N1 C5 . 1.373(5) ?
N1 N2 . 1.395(4) ?
N1 H1N . 0.92(4) ?
N2 C6 . 1.315(5) ?
N2 H2N . 1.00(4) ?
C1 C2 . 1.352(5) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.417(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.374(5) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.455(5) ?
C6 C8 . 1.423(5) ?
C6 C7 . 1.489(5) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 C16 . 1.441(5) ?
C8 C9 . 1.454(5) ?
C10 C11 . 1.380(5) ?
C10 C15 . 1.390(5) ?
C11 C12 . 1.380(6) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.402(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.376(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.387(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.465(5) ?
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
N2 H2N O4 . 1.00(4) 1.64(5) 2.481(4) 140(4)
N1 H1N O1 1_655 0.92(4) 1.93(4) 2.841(4) 177(4)
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
C5 N1 N2 C6 . . . . -153.1(4) ?
C4 S1 C1 C2 . . . . -1.1(3) ?
S1 C1 C2 C3 . . . . 1.3(5) ?
C1 C2 C3 C4 . . . . -0.9(5) ?
C2 C3 C4 C5 . . . . -175.5(4) ?
C2 C3 C4 S1 . . . . 0.0(5) ?
C1 S1 C4 C3 . . . . 0.6(3) ?
C1 S1 C4 C5 . . . . 176.6(3) ?
N2 N1 C5 O1 . . . . 8.1(5) ?
N2 N1 C5 C4 . . . . -174.8(3) ?
C3 C4 C5 O1 . . . . 148.8(4) ?
S1 C4 C5 O1 . . . . -26.4(6) ?
C3 C4 C5 N1 . . . . -28.2(6) ?
S1 C4 C5 N1 . . . . 156.6(3) ?
N1 N2 C6 C8 . . . . 179.3(3) ?
N1 N2 C6 C7 . . . . 1.2(6) ?
N2 C6 C8 C16 . . . . -3.4(5) ?
C7 C6 C8 C16 . . . . 174.5(4) ?
N2 C6 C8 C9 . . . . 176.4(3) ?
C7 C6 C8 C9 . . . . -5.7(6) ?
C10 O2 C9 O3 . . . . -174.9(3) ?
C10 O2 C9 C8 . . . . 6.2(5) ?
C6 C8 C9 O3 . . . . -2.9(6) ?
C16 C8 C9 O3 . . . . 176.9(4) ?
C6 C8 C9 O2 . . . . 175.9(3) ?
C16 C8 C9 O2 . . . . -4.3(5) ?
C9 O2 C10 C11 . . . . 176.6(4) ?
C9 O2 C10 C15 . . . . -3.5(5) ?
O2 C10 C11 C12 . . . . 179.0(3) ?
C15 C10 C11 C12 . . . . -1.0(6) ?
C10 C11 C12 C13 . . . . -0.2(6) ?
C11 C12 C13 C14 . . . . 0.5(6) ?
C12 C13 C14 C15 . . . . 0.4(6) ?
C13 C14 C15 C10 . . . . -1.5(6) ?
C13 C14 C15 C16 . . . . -178.2(4) ?
C11 C10 C15 C14 . . . . 1.8(6) ?
O2 C10 C15 C14 . . . . -178.1(3) ?
C11 C10 C15 C16 . . . . 178.7(4) ?
O2 C10 C15 C16 . . . . -1.3(6) ?
C6 C8 C16 O4 . . . . -1.3(6) ?
C9 C8 C16 O4 . . . . 178.9(4) ?
C6 C8 C16 C15 . . . . 179.6(3) ?
C9 C8 C16 C15 . . . . -0.2(5) ?
C14 C15 C16 O4 . . . . 0.5(6) ?
C10 C15 C16 O4 . . . . -176.2(3) ?
C14 C15 C16 C8 . . . . 179.7(4) ?
C10 C15 C16 C8 . . . . 3.0(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656613
