#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/54/2205421.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_2205421
loop_
_publ_author_name
'Ali, Hapipah M.'
'Puvaneswary, Subramaniam'
'Basirun, Wan Jefri'
'Ng, Seik Weng'
_publ_section_title
;
 3-Hydroxysalicylaldehyde 2-furoylhydrazone
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1079
_journal_page_last               o1080
_journal_paper_doi               10.1107/S1600536805008391
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H10 N2 O4'
_chemical_formula_moiety         'C12 H10 N2 O4'
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22
_chemical_name_systematic
;
3-Hydroxysalicylaldehyde 2-furoylhydrazone
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.1200(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2143(8)
_cell_length_b                   9.3730(7)
_cell_length_c                   11.4149(9)
_cell_measurement_reflns_used    2381
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.2
_cell_volume                     1133.65(15)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'medium-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_sigmaI/netI    0.022
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6280
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.041
_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)+(0.0624P)²+0.2675P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.110
_refine_ls_wR_factor_ref         0.127
_reflns_number_gt                1703
_reflns_number_total             2461
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6627.cif
_cod_data_source_block           I
_cod_original_cell_volume        1133.7(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2205421
_cod_database_fobs_code          2205421
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_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_type_symbol
O1 0.14040(10) 0.5056(2) 0.24300(10) 0.0577(4) Uani d D 1 O
O2 0.33820(10) 0.66840(10) 0.29960(10) 0.0552(4) Uani d D 1 O
O3 0.60010(10) 0.9299(2) 0.30820(10) 0.0575(4) Uani d . 1 O
O4 0.78960(10) 1.1196(2) 0.37350(10) 0.0724(5) Uani d . 1 O
N1 0.52790(10) 0.7832(2) 0.47210(10) 0.0450(4) Uani d . 1 N
N2 0.63140(10) 0.8709(2) 0.50840(10) 0.0465(4) Uani d D 1 N
C1 0.3156(2) 0.6016(2) 0.39590(10) 0.0404(4) Uani d . 1 C
C2 0.2104(2) 0.5132(2) 0.3661(2) 0.0440(4) Uani d . 1 C
C3 0.1818(2) 0.4399(2) 0.4575(2) 0.0572(5) Uani d D 1 C
C4 0.2556(2) 0.4551(2) 0.5803(2) 0.0630(6) Uani d D 1 C
C5 0.3587(2) 0.5432(2) 0.6110(2) 0.0553(5) Uani d D 1 C
C6 0.3909(2) 0.6187(2) 0.5201(2) 0.0422(4) Uani d . 1 C
C7 0.5002(2) 0.7123(2) 0.5555(2) 0.0460(4) Uani d D 1 C
C8 0.6607(2) 0.9423(2) 0.41940(10) 0.0419(4) Uani d . 1 C
C9 0.7689(2) 1.0381(2) 0.4633(2) 0.0437(4) Uani d . 1 C
C10 0.8530(2) 1.0716(2) 0.5733(2) 0.0590(5) Uani d D 1 C
C11 0.9319(2) 1.1782(3) 0.5512(2) 0.0688(6) Uani d D 1 C
C12 0.8894(2) 1.2032(3) 0.4309(2) 0.0771(7) Uani d D 1 C
H1o 0.0670(10) 0.473(2) 0.235(2) 0.083(8) Uiso d D 1 H
H2o 0.402(2) 0.723(2) 0.330(2) 0.096(9) Uiso d D 1 H
H2n 0.668(2) 0.884(2) 0.5860(10) 0.063(6) Uiso d D 1 H
H3 0.1100(10) 0.380(2) 0.436(2) 0.076(7) Uiso d D 1 H
H4 0.234(2) 0.406(2) 0.643(2) 0.077(7) Uiso d D 1 H
H5 0.407(2) 0.556(2) 0.6970(10) 0.065(6) Uiso d D 1 H
H7 0.551(2) 0.719(2) 0.6410(10) 0.052(5) Uiso d D 1 H
H10 0.857(2) 1.032(2) 0.6500(10) 0.066(6) Uiso d D 1 H
H11 1.003(2) 1.224(2) 0.608(2) 0.075(6) Uiso d D 1 H
H12 0.915(2) 1.269(2) 0.379(2) 0.093(8) Uiso d D 1 H
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
_geom_angle_publ_flag
C9 O4 C12 106.3(2) yes
N2 N1 C7 118.30(10) yes
N1 N2 C8 117.50(10) yes
O2 C1 C2 116.40(10) no
O2 C1 C6 123.80(10) no
C2 C1 C6 119.80(10) no
O1 C2 C3 123.8(2) no
O1 C2 C1 116.00(10) no
C3 C2 C1 120.3(2) no
C2 C3 C4 120.5(2) no
C4 C5 C6 121.1(2) no
C5 C4 C3 119.8(2) no
C5 C6 C1 118.5(2) no
C5 C6 C7 120.0(2) no
C1 C6 C7 121.6(2) no
N1 C7 C6 119.7(2) yes
O3 C8 N2 122.8(2) yes
O3 C8 C9 121.8(2) yes
N2 C8 C9 115.30(10) yes
O4 C9 C8 114.50(10) yes
O4 C9 C10 109.5(2) yes
C10 C9 C8 135.9(2) no
C9 C10 C11 106.8(2) no
C12 C11 C10 106.2(2) no
C11 C12 O4 111.2(2) no
C2 O1 H1o 110(2) no
C1 O2 H2o 107(2) no
C8 N2 H2n 124.0(10) no
N1 N2 H2n 118.0(10) no
C2 C3 H3 119.0(10) no
C4 C3 H3 120.0(10) no
C5 C4 H4 120.0(10) no
C3 C4 H4 120.0(10) no
C4 C5 H5 119.0(10) no
C6 C5 H5 120.0(10) no
N1 C7 H7 121.0(10) no
C6 C7 H7 119.0(10) no
C9 C10 H10 126.0(10) no
C11 C10 H10 127.0(10) no
C12 C11 H11 124.0(10) no
C10 C11 H11 130.0(10) no
C11 C12 H12 133(2) no
O4 C12 H12 116(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.368(2) yes
O2 C1 1.359(2) yes
O3 C8 1.233(2) yes
O4 C9 1.358(2) yes
O4 C12 1.348(3) yes
N1 N2 1.371(2) yes
N1 C7 1.280(2) yes
N2 C8 1.344(2) yes
C1 C2 1.390(2) no
C1 C6 1.402(2) no
C2 C3 1.372(2) no
C3 C4 1.382(3) no
C4 C5 1.370(3) no
C5 C6 1.397(2) no
C5 H5 0.955(9) no
C6 C7 1.453(2) no
C8 C9 1.460(2) no
C9 C10 1.338(2) no
C10 C11 1.411(3) no
C11 C12 1.319(3) no
O1 H1o 0.86(10) no
O2 H2o 0.860(10) no
N2 H2n 0.850(10) no
C3 H3 0.950(10) no
C4 H4 0.950(10) no
C7 H7 0.950(10) no
C10 H10 0.940(10) no
C11 H11 0.950(10) no
C12 H12 0.960(10) no
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
O1 H1o O3 4_656 0.860(10) 1.820(10) 2.662(2) 169(2) yes
O2 H2o N1 . 0.860(10) 1.85(2) 2.611(2) 147(2) yes
N2 H2n O1 2_565 0.850(10) 2.18(2) 2.890(2) 141(2) yes
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
C1 C6 C7 N1 1.3(3) yes
C7 N1 N2 C8 178.6(2) yes
C6 C7 N1 N2 179.8(2) yes
N1 N2 C8 O3 -1.3(2) yes
N1 N2 C8 C9 177.80(10) yes
O3 C8 C9 O4 5.3(2) yes
O2 C1 C2 O1 -1.1(2) no
C6 C1 C2 O1 178.3(2) no
O2 C1 C2 C3 179.0(2) no
C6 C1 C2 C3 -1.6(3) no
O1 C2 C3 C4 -178.7(2) no
C1 C2 C3 C4 1.2(3) no
C2 C3 C4 C5 -0.4(3) no
C3 C4 C5 C6 0.0(3) no
C4 C5 C6 C1 -0.4(3) no
C4 C5 C6 C7 179.6(2) no
O2 C1 C6 C5 -179.4(2) no
C2 C1 C6 C5 1.2(3) no
O2 C1 C6 C7 0.6(3) no
C2 C1 C6 C7 -178.8(2) no
C5 C6 C7 N1 -178.7(2) no
C12 O4 C9 C10 0.6(2) no
C12 O4 C9 C8 178.2(2) no
O3 C8 C9 C10 -178.0(2) no
N2 C8 C9 C10 2.9(3) no
N2 C8 C9 O4 -173.8(2) no
O4 C9 C10 C11 -0.9(2) no
C8 C9 C10 C11 -177.8(2) no
C9 C10 C11 C12 0.9(3) no
C10 C11 C12 O4 -0.6(3) no
C9 O4 C12 C11 0.0(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654791
