#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/21/2212106.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_2212106
loop_
_publ_author_name
'Zhou, Qing-Li'
'Wang, Chang-Lu'
'Jing, Zuo-Liang'
_publ_section_title
;
 2'-(1,3-Benzodioxol-5-ylmethylene)furan-2-carbohydrazide
;
_journal_coeditor_code           CI2279
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o898
_journal_page_last               o899
_journal_paper_doi               10.1107/S160053680700308X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H10 N2 O4'
_chemical_formula_moiety         'C13 H10 N2 O4'
_chemical_formula_sum            'C13 H10 N2 O4'
_chemical_formula_weight         258.23
_chemical_name_systematic
;
2'-(1,3-Benzodioxol-5-ylmethylene)furan-2-carbohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 95.079(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8351(7)
_cell_length_b                   11.3996(8)
_cell_length_c                   10.4260(7)
_cell_measurement_reflns_used    1924
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.0
_cell_volume                     1164.33(14)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2005)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1996)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10631
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0850P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1596
_reflns_number_gt                1672
_reflns_number_total             2704
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2279.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2212106
_cod_database_fobs_code          2212106
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
O O1 0.23650(14) 0.20846(13) 0.05750(13) 0.0248(4) Uani d . 1
O O2 -0.06964(14) 0.13427(13) -0.13460(13) 0.0254(4) Uani d . 1
O O3 0.25311(17) 0.60059(13) 0.55773(14) 0.0326(4) Uani d . 1
O O4 0.11752(18) 0.76555(14) 0.56993(14) 0.0370(5) Uani d . 1
N N1 0.02494(18) 0.29134(15) 0.05140(16) 0.0209(4) Uani d . 1
H H1 -0.066(2) 0.281(2) 0.023(2) 0.031 Uiso d . 1
N N2 0.06763(17) 0.36980(15) 0.14795(15) 0.0218(4) Uani d . 1
C C1 0.1155(2) 0.21040(18) 0.01564(18) 0.0195(4) Uani d . 1
C C2 0.06299(19) 0.12514(18) -0.08041(19) 0.0205(5) Uani d . 1
C C3 0.1247(2) 0.03295(19) -0.1338(2) 0.0289(5) Uani d . 1
H H3 0.2160 0.0073 -0.1136 0.035 Uiso calc R 1
C C4 0.0276(2) -0.0174(2) -0.2244(2) 0.0308(6) Uani d . 1
H H4 0.0408 -0.0836 -0.2772 0.037 Uiso calc R 1
C C5 -0.0874(3) 0.0460(2) -0.2222(2) 0.0324(6) Uani d . 1
H H5 -0.1696 0.0312 -0.2746 0.039 Uiso calc R 1
C C6 -0.0152(2) 0.45398(18) 0.16670(19) 0.0229(5) Uani d . 1
H H6 -0.0978 0.4617 0.1129 0.028 Uiso calc R 1
C C7 0.0180(2) 0.53788(18) 0.27093(18) 0.0195(5) Uani d . 1
C C8 0.1300(2) 0.51923(17) 0.36270(19) 0.0217(5) Uani d . 1
H H8 0.1874 0.4525 0.3586 0.026 Uiso calc R 1
C C9 0.1524(2) 0.60084(18) 0.45736(19) 0.0215(5) Uani d . 1
C C10 0.0715(2) 0.69973(19) 0.46400(19) 0.0246(5) Uani d . 1
C C11 -0.0371(2) 0.72126(19) 0.3769(2) 0.0280(5) Uani d . 1
H H11 -0.0921 0.7893 0.3819 0.034 Uiso calc R 1
C C12 -0.0633(2) 0.63748(18) 0.27954(19) 0.0223(5) Uani d . 1
H H12 -0.1388 0.6488 0.2174 0.027 Uiso calc R 1
C C13 0.2365(3) 0.7072(2) 0.6263(2) 0.0337(6) Uani d . 1
H H13A 0.3177 0.7578 0.6214 0.040 Uiso calc R 1
H H13B 0.2265 0.6901 0.7181 0.040 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 O2 C2 106.26(17)
C9 O3 C13 105.85(16)
C10 O4 C13 105.99(16)
C1 N1 N2 118.35(17)
C1 N1 H1 118.0(14)
N2 N1 H1 122.2(14)
C6 N2 N1 115.97(18)
O1 C1 N1 123.51(19)
O1 C1 C2 120.30(18)
N1 C1 C2 116.16(18)
C3 C2 O2 109.36(19)
C3 C2 C1 130.9(2)
O2 C2 C1 119.76(17)
C2 C3 C4 106.9(2)
C2 C3 H3 126.6
C4 C3 H3 126.6
C5 C4 C3 107.0(2)
C5 C4 H4 126.5
C3 C4 H4 126.5
C4 C5 O2 110.5(2)
C4 C5 H5 124.7
O2 C5 H5 124.7
N2 C6 C7 119.9(2)
N2 C6 H6 120.0
C7 C6 H6 120.0
C12 C7 C8 119.77(18)
C12 C7 C6 119.23(19)
C8 C7 C6 120.99(19)
C9 C8 C7 117.12(19)
C9 C8 H8 121.4
C7 C8 H8 121.4
C8 C9 O3 127.60(19)
C8 C9 C10 122.42(19)
O3 C9 C10 109.98(18)
C11 C10 O4 128.2(2)
C11 C10 C9 122.26(19)
O4 C10 C9 109.51(18)
C10 C11 C12 116.3(2)
C10 C11 H11 121.8
C12 C11 H11 121.8
C7 C12 C11 122.10(19)
C7 C12 H12 119.0
C11 C12 H12 119.0
O3 C13 O4 108.46(17)
O3 C13 H13A 110.0
O4 C13 H13A 110.0
O3 C13 H13B 110.0
O4 C13 H13B 110.0
H13A C13 H13B 108.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.231(2)
O2 C5 1.360(2)
O2 C2 1.379(2)
O3 C9 1.376(2)
O3 C13 1.427(2)
O4 C10 1.378(2)
O4 C13 1.427(3)
N1 C1 1.357(3)
N1 N2 1.384(2)
N1 H1 0.93(2)
N2 C6 1.285(3)
C1 C2 1.457(3)
C2 C3 1.357(3)
C3 C4 1.405(3)
C3 H3 0.95
C4 C5 1.344(3)
C4 H4 0.95
C5 H5 0.95
C6 C7 1.463(3)
C6 H6 0.95
C7 C12 1.396(3)
C7 C8 1.410(3)
C8 C9 1.360(3)
C8 H8 0.95
C9 C10 1.385(3)
C10 C11 1.362(3)
C11 C12 1.401(3)
C11 H11 0.95
C12 H12 0.95
C13 H13A 0.99
C13 H13B 0.99
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
_geom_hbond_publ_flag
N1 H1 O1 4_565 0.93(2) 2.01(2) 2.843(2) 150(2) y
C4 H4 O4 1_544 0.95 2.51 3.441(3) 168 y
C5 H5 O3 4_564 0.95 2.38 3.143(3) 137 y
C6 H6 O1 4_565 0.95 2.57 3.193(2) 124 y
C13 H13B O1 2_556 0.99 2.35 3.284(2) 158 y
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
C1 N1 N2 C6 171.16(18)
N2 N1 C1 O1 -5.7(3)
N2 N1 C1 C2 176.16(16)
C5 O2 C2 C3 -0.2(2)
C5 O2 C2 C1 178.18(18)
O1 C1 C2 C3 3.4(3)
N1 C1 C2 C3 -178.3(2)
O1 C1 C2 O2 -174.50(17)
N1 C1 C2 O2 3.7(3)
O2 C2 C3 C4 0.0(2)
C1 C2 C3 C4 -178.1(2)
C2 C3 C4 C5 0.1(3)
C3 C4 C5 O2 -0.2(3)
C2 O2 C5 C4 0.2(2)
N1 N2 C6 C7 176.93(16)
N2 C6 C7 C12 171.50(19)
N2 C6 C7 C8 -8.8(3)
C12 C7 C8 C9 0.5(3)
C6 C7 C8 C9 -179.14(17)
C7 C8 C9 O3 178.92(19)
C7 C8 C9 C10 -1.1(3)
C13 O3 C9 C8 177.5(2)
C13 O3 C9 C10 -2.5(2)
C13 O4 C10 C11 -178.1(2)
C13 O4 C10 C9 3.2(2)
C8 C9 C10 C11 0.8(3)
O3 C9 C10 C11 -179.22(19)
C8 C9 C10 O4 179.54(18)
O3 C9 C10 O4 -0.5(2)
O4 C10 C11 C12 -178.36(19)
C9 C10 C11 C12 0.1(3)
C8 C7 C12 C11 0.3(3)
C6 C7 C12 C11 -179.97(18)
C10 C11 C12 C7 -0.7(3)
C9 O3 C13 O4 4.4(2)
C10 O4 C13 O3 -4.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4488308
