#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/69/2226913.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_2226913
loop_
_publ_author_name
'Li, Yu-Feng'
'Jian, Fang-Fang'
_publ_section_title
;
 N'-(3,4-Dimethylbenzylidene)furan-2-carbohydrazide
;
_journal_coeditor_code           HB5553
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2061
_journal_paper_doi               10.1107/S1600536810027959
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H14 N2 O2'
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_chemical_name_systematic
;
N'-(3,4-Dimethylbenzylidene)furan-2-carbohydrazide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.655(3)
_cell_length_b                   7.6304(15)
_cell_length_c                   19.020(4)
_cell_measurement_reflns_used    1563
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.10
_cell_volume                     2562.3(9)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 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  0.1266
_diffrn_reflns_av_sigmaI/netI    0.0750
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21744
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0658
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1773
_reflns_number_gt                1563
_reflns_number_total             2921
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5553.cif
_cod_data_source_block           I
_cod_database_code               2226913
_cod_database_fobs_code          2226913
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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
O O2 0.34251(10) 0.2908(2) 0.40087(10) 0.0493(5) Uani d . 1 . .
N N2 0.23842(12) 0.1209(2) 0.38067(10) 0.0404(5) Uani d . 1 . .
H H2A 0.2147 0.0251 0.3897 0.048 Uiso calc R 1 . .
N N1 0.20989(11) 0.2401(3) 0.33290(10) 0.0391(5) Uani d . 1 . .
C C1 0.32632(14) 0.0301(3) 0.46664(13) 0.0393(6) Uani d . 1 . .
C C6 0.15127(14) 0.1915(3) 0.29934(12) 0.0412(6) Uani d . 1 . .
H H6A 0.1308 0.0813 0.3079 0.049 Uiso calc R 1 . .
C C5 0.30454(14) 0.1586(3) 0.41282(12) 0.0384(6) Uani d . 1 . .
C C7 0.11563(14) 0.3062(3) 0.24746(12) 0.0397(6) Uani d . 1 . .
C C9 0.11430(15) 0.5784(3) 0.18082(13) 0.0456(7) Uani d . 1 . .
C C4 0.40945(19) -0.1050(4) 0.53228(14) 0.0580(8) Uani d . 1 . .
H H4A 0.4554 -0.1425 0.5508 0.070 Uiso calc R 1 . .
C C8 0.14661(15) 0.4693(3) 0.23064(13) 0.0439(7) Uani d . 1 . .
H H8A 0.1903 0.5058 0.2536 0.053 Uiso calc R 1 . .
C C2 0.28720(16) -0.0713(3) 0.51175(13) 0.0469(7) Uani d . 1 . .
H H2B 0.2348 -0.0819 0.5147 0.056 Uiso calc R 1 . .
C C12 0.04994(14) 0.2541(3) 0.21381(12) 0.0441(7) Uani d . 1 . .
H H12A 0.0277 0.1472 0.2249 0.053 Uiso calc R 1 . .
C C11 0.01738(15) 0.3619(4) 0.16343(13) 0.0475(7) Uani d . 1 . .
H H11A -0.0265 0.3252 0.1407 0.057 Uiso calc R 1 . .
C C3 0.34193(18) -0.1595(4) 0.55411(14) 0.0532(7) Uani d . 1 . .
H H3A 0.3323 -0.2394 0.5899 0.064 Uiso calc R 1 . .
C C14 0.1495(2) 0.7546(4) 0.16590(19) 0.0728(10) Uani d . 1 . .
H H14A 0.1940 0.7691 0.1944 0.109 Uiso calc R 1 . .
H H14B 0.1138 0.8455 0.1767 0.109 Uiso calc R 1 . .
H H14C 0.1632 0.7614 0.1171 0.109 Uiso calc R 1 . .
C C13 0.01177(19) 0.6353(4) 0.09024(15) 0.0709(9) Uani d . 1 . .
H H13A -0.0325 0.5771 0.0724 0.106 Uiso calc R 1 . .
H H13B 0.0470 0.6543 0.0525 0.106 Uiso calc R 1 . .
H H13C -0.0025 0.7459 0.1103 0.106 Uiso calc R 1 . .
O O1 0.40208(10) 0.0140(3) 0.47873(9) 0.0542(6) Uani d . 1 . .
C C10 0.04847(15) 0.5226(4) 0.14611(12) 0.0459(7) 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'
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
C5 N2 N1 . . 118.3(2) ?
C5 N2 H2A . . 120.9 ?
N1 N2 H2A . . 120.9 ?
C6 N1 N2 . . 115.8(2) ?
C2 C1 O1 . . 110.1(2) ?
C2 C1 C5 . . 133.9(2) ?
O1 C1 C5 . . 115.8(2) ?
N1 C6 C7 . . 121.0(2) ?
N1 C6 H6A . . 119.5 ?
C7 C6 H6A . . 119.5 ?
O2 C5 N2 . . 124.2(2) ?
O2 C5 C1 . . 122.2(2) ?
N2 C5 C1 . . 113.6(2) ?
C12 C7 C8 . . 118.6(2) ?
C12 C7 C6 . . 120.1(2) ?
C8 C7 C6 . . 121.3(2) ?
C8 C9 C10 . . 118.7(2) ?
C8 C9 C14 . . 119.7(3) ?
C10 C9 C14 . . 121.6(2) ?
C3 C4 O1 . . 110.8(3) ?
C3 C4 H4A . . 124.6 ?
O1 C4 H4A . . 124.6 ?
C9 C8 C7 . . 122.1(2) ?
C9 C8 H8A . . 118.9 ?
C7 C8 H8A . . 118.9 ?
C1 C2 C3 . . 106.5(3) ?
C1 C2 H2B . . 126.8 ?
C3 C2 H2B . . 126.8 ?
C7 C12 C11 . . 119.8(2) ?
C7 C12 H12A . . 120.1 ?
C11 C12 H12A . . 120.1 ?
C10 C11 C12 . . 121.7(3) ?
C10 C11 H11A . . 119.1 ?
C12 C11 H11A . . 119.1 ?
C4 C3 C2 . . 106.5(3) ?
C4 C3 H3A . . 126.8 ?
C2 C3 H3A . . 126.8 ?
C9 C14 H14A . . 109.5 ?
C9 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C9 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C1 O1 C4 . . 106.2(2) ?
C11 C10 C9 . . 119.1(2) ?
C11 C10 C13 . . 120.1(3) ?
C9 C10 C13 . . 120.9(3) ?
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
O2 C5 . 1.232(3) ?
N2 C5 . 1.349(3) ?
N2 N1 . 1.381(3) ?
N2 H2A . 0.8600 ?
N1 C6 . 1.271(3) ?
C1 C2 . 1.346(4) ?
C1 O1 . 1.363(3) ?
C1 C5 . 1.469(3) ?
C6 C7 . 1.462(3) ?
C6 H6A . 0.9300 ?
C7 C12 . 1.383(3) ?
C7 C8 . 1.396(4) ?
C9 C8 . 1.384(3) ?
C9 C10 . 1.403(4) ?
C9 C14 . 1.508(4) ?
C4 C3 . 1.329(4) ?
C4 O1 . 1.371(3) ?
C4 H4A . 0.9300 ?
C8 H8A . 0.9300 ?
C2 C3 . 1.427(4) ?
C2 H2B . 0.9300 ?
C12 C11 . 1.388(4) ?
C12 H12A . 0.9300 ?
C11 C10 . 1.383(4) ?
C11 H11A . 0.9300 ?
C3 H3A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C13 C10 . 1.513(4) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 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
N2 H2A O2 7_655 0.86 2.06 2.921(3) 174
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 22827579
