#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/96/2219602.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_2219602
loop_
_publ_author_name
'Ma, Qi'
'Lu, Li-Ping'
'Zhu, Miao-Li'
_publ_section_title
;
 1,2-Bis(2-furylmethylene)hydrazine
;
_journal_coeditor_code           HB2802
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2026
_journal_paper_doi               10.1107/S1600536808030729
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H8 N2 O2'
_chemical_formula_moiety         'C10 H8 N2 O2'
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18
_chemical_name_systematic
;
1,2-Bis(2-furylmethylene)hydrazine
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.877(2)
_cell_length_b                   8.996(3)
_cell_length_c                   15.171(4)
_cell_measurement_reflns_used    5207
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.62
_cell_volume                     938.6(5)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_diffrn_measurement_method       ω
_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  0.0806
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4129
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0386
_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)+(0.0662P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                677
_reflns_number_total             829
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2802.cif
_cod_data_source_block           I
_cod_database_code               2219602
_cod_database_fobs_code          2219602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
C C1 -0.0467(2) 0.88870(18) 0.18436(11) 0.0736(5) Uani d . 1
H H1 -0.0937 0.8074 0.2157 0.088 Uiso calc R 1
C C2 -0.1336(2) 1.01970(19) 0.18094(10) 0.0719(5) Uani d . 1
H H2 -0.2492 1.0466 0.2084 0.086 Uiso calc R 1
C C3 -0.0168(2) 1.10963(17) 0.12769(10) 0.0642(5) Uani d . 1
H H3 -0.0400 1.2085 0.1131 0.077 Uiso calc R 1
C C4 0.13456(19) 1.02755(14) 0.10149(8) 0.0529(4) Uani d . 1
C C5 0.2964(2) 1.06191(15) 0.04628(9) 0.0566(4) Uani d . 1
H H5 0.3049 1.1570 0.0225 0.068 Uiso calc R 1
N N1 0.42950(18) 0.96866(13) 0.02805(8) 0.0613(4) Uani d . 1
O O1 0.12017(16) 0.88799(10) 0.13632(7) 0.0669(4) Uani d . 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
C1 0.0695(10) 0.0698(11) 0.0815(11) -0.0135(8) 0.0114(9) 0.0137(8)
C2 0.0637(10) 0.0800(12) 0.0721(11) 0.0049(8) 0.0084(7) 0.0085(8)
C3 0.0722(11) 0.0589(10) 0.0616(9) 0.0093(7) 0.0038(7) 0.0082(7)
C4 0.0639(9) 0.0452(8) 0.0496(7) -0.0049(6) -0.0044(6) 0.0007(6)
C5 0.0690(10) 0.0485(8) 0.0522(8) -0.0055(7) 0.0007(7) 0.0013(6)
N1 0.0649(8) 0.0541(8) 0.0649(8) -0.0033(6) 0.0084(5) 0.0045(5)
O1 0.0698(8) 0.0479(7) 0.0830(8) -0.0029(5) 0.0078(5) 0.0057(4)
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_site_symmetry_3
_geom_angle
C2 C1 O1 . 111.39(14)
C2 C1 H1 . 124.3
O1 C1 H1 . 124.3
C1 C2 C3 . 106.18(15)
C1 C2 H2 . 126.9
C3 C2 H2 . 126.9
C4 C3 C2 . 107.45(14)
C4 C3 H3 . 126.3
C2 C3 H3 . 126.3
C3 C4 O1 . 109.66(12)
C3 C4 C5 . 131.47(13)
O1 C4 C5 . 118.87(12)
N1 C5 C4 . 123.10(13)
N1 C5 H5 . 118.4
C4 C5 H5 . 118.4
C5 N1 N1 5_675 111.29(15)
C1 O1 C4 . 105.32(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.322(2)
C1 O1 . 1.359(2)
C1 H1 . 0.9300
C2 C3 . 1.397(2)
C2 H2 . 0.9300
C3 C4 . 1.3364(19)
C3 H3 . 0.9300
C4 O1 . 1.3657(16)
C4 C5 . 1.427(2)
C5 N1 . 1.2721(18)
C5 H5 . 0.9300
N1 N1 5_675 1.408(2)
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_4
_geom_torsion
O1 C1 C2 C3 . -0.05(19)
C1 C2 C3 C4 . 0.23(18)
C2 C3 C4 O1 . -0.32(17)
C2 C3 C4 C5 . 179.42(15)
C3 C4 C5 N1 . 179.91(15)
O1 C4 C5 N1 . -0.4(2)
C4 C5 N1 N1 5_675 179.64(14)
C2 C1 O1 C4 . -0.14(18)
C3 C4 O1 C1 . 0.29(16)
C5 C4 O1 C1 . -179.49(12)
