#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/77/2227786.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227786
loop_
_publ_author_name
'Li, Yu-Feng'
'Meng, Fan-Yong'
_publ_section_title
;
 N'-[4-(Dimethylamino)benzylidene]furan-2-carbohydrazide
;
_journal_coeditor_code           LH5131
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2696
_journal_paper_doi               10.1107/S1600536810037244
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H15 N3 O2'
_chemical_formula_moiety         'C14 H15 N3 O2'
_chemical_formula_sum            'C14 H15 N3 O2'
_chemical_formula_weight         257.29
_chemical_name_systematic
;
N'-[4-(Dimethylamino)benzylidene]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                   10.866(2)
_cell_length_b                   7.9654(16)
_cell_length_c                   30.620(6)
_cell_measurement_reflns_used    986
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      3.24
_cell_volume                     2650.2(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω 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  0.1720
_diffrn_reflns_av_sigmaI/netI    0.4259
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            18964
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.158
_refine_ls_goodness_of_fit_ref   0.746
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.746
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0687P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                986
_reflns_number_total             2394
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5131.cif
_cod_data_source_block           I
_cod_database_code               2227786
_cod_database_fobs_code          2227786
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
N N2 0.2524(2) 0.2706(3) 0.07906(7) 0.0526(7) Uani d . 1 . .
H H2A 0.2085 0.3518 0.0691 0.063 Uiso calc R 1 . .
N N1 0.2357(2) 0.2125(3) 0.12126(7) 0.0522(7) Uani d . 1 . .
C C9 0.2087(3) 0.1579(4) 0.25849(9) 0.0565(9) Uani d . 1 . .
H H9A 0.2642 0.0921 0.2740 0.068 Uiso calc R 1 . .
O O2 0.39675(19) 0.0722(3) 0.06431(6) 0.0592(6) Uani d . 1 . .
C C7 0.1388(2) 0.2646(4) 0.18944(8) 0.0440(7) Uani d . 1 . .
C C10 0.1164(3) 0.2436(4) 0.28088(9) 0.0513(8) Uani d . 1 . .
O O1 0.3004(2) 0.4211(3) 0.00187(6) 0.0778(8) Uani d . 1 . .
C C12 0.0460(3) 0.3471(4) 0.21190(9) 0.0527(8) Uani d . 1 . .
H H12A -0.0101 0.4112 0.1962 0.063 Uiso calc R 1 . .
C C11 0.0337(3) 0.3379(4) 0.25639(9) 0.0544(9) Uani d . 1 . .
H H11A -0.0300 0.3949 0.2702 0.065 Uiso calc R 1 . .
C C5 0.3391(3) 0.1974(4) 0.05371(9) 0.0496(8) Uani d . 1 . .
N N3 0.1068(3) 0.2355(4) 0.32592(8) 0.0705(9) Uani d . 1 . .
C C6 0.1552(3) 0.2950(4) 0.14317(9) 0.0487(8) Uani d . 1 . .
H H6A 0.1070 0.3751 0.1292 0.058 Uiso calc R 1 . .
C C14 0.1968(7) 0.1475(9) 0.35123(15) 0.0956(16) Uani d . 1 . .
C C8 0.2191(3) 0.1689(4) 0.21414(9) 0.0517(8) Uani d . 1 . .
H H8A 0.2819 0.1105 0.2002 0.062 Uiso calc R 1 . .
C C2 0.3436(4) 0.4699(6) -0.03795(11) 0.0939(14) Uani d . 1 . .
H H2B 0.3175 0.5649 -0.0529 0.113 Uiso calc R 1 . .
C C4 0.3625(3) 0.2785(4) 0.01224(9) 0.0533(9) Uani d . 1 . .
C C1 0.4275(4) 0.3640(5) -0.05229(11) 0.0846(13) Uani d . 1 . .
H H1B 0.4701 0.3704 -0.0786 0.101 Uiso calc R 1 . .
C C13 0.0192(5) 0.3396(9) 0.34859(14) 0.0881(15) Uani d . 1 . .
C C3 0.4401(3) 0.2390(4) -0.01997(10) 0.0698(10) Uani d . 1 . .
H H3A 0.4925 0.1467 -0.0209 0.084 Uiso calc R 1 . .
H H13A 0.025(4) 0.306(5) 0.3795(14) 0.127(16) Uiso d . 1 . .
H H13B -0.057(5) 0.330(7) 0.3362(15) 0.15(2) Uiso d . 1 . .
H H14A 0.202(4) 0.030(7) 0.3405(13) 0.13(2) Uiso d . 1 . .
H H13C 0.038(6) 0.456(8) 0.3456(16) 0.18(3) Uiso d . 1 . .
H H14B 0.168(4) 0.141(6) 0.3805(17) 0.148(19) Uiso d . 1 . .
H H14C 0.273(7) 0.198(11) 0.352(2) 0.24(4) Uiso 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 . . 118.9(3) ?
C5 N2 H2A . . 120.6 ?
N1 N2 H2A . . 120.6 ?
C6 N1 N2 . . 114.0(3) ?
C8 C9 C10 . . 121.2(3) ?
C8 C9 H9A . . 119.4 ?
C10 C9 H9A . . 119.4 ?
C8 C7 C12 . . 116.7(3) ?
C8 C7 C6 . . 123.3(3) ?
C12 C7 C6 . . 119.8(3) ?
C11 C10 C9 . . 117.7(3) ?
C11 C10 N3 . . 120.9(3) ?
C9 C10 N3 . . 121.4(3) ?
C4 O1 C2 . . 106.0(3) ?
C11 C12 C7 . . 122.6(3) ?
C11 C12 H12A . . 118.7 ?
C7 C12 H12A . . 118.7 ?
C12 C11 C10 . . 120.1(3) ?
C12 C11 H11A . . 119.9 ?
C10 C11 H11A . . 119.9 ?
O2 C5 N2 . . 123.8(3) ?
O2 C5 C4 . . 120.5(3) ?
N2 C5 C4 . . 115.7(3) ?
C10 N3 C14 . . 120.7(3) ?
C10 N3 C13 . . 120.2(3) ?
C14 N3 C13 . . 118.2(4) ?
N1 C6 C7 . . 120.7(3) ?
N1 C6 H6A . . 119.7 ?
C7 C6 H6A . . 119.7 ?
N3 C14 H14A . . 109(3) ?
N3 C14 H14B . . 108(3) ?
H14A C14 H14B . . 106(4) ?
N3 C14 H14C . . 115(5) ?
H14A C14 H14C . . 112(6) ?
H14B C14 H14C . . 107(4) ?
C9 C8 C7 . . 121.7(3) ?
C9 C8 H8A . . 119.1 ?
C7 C8 H8A . . 119.1 ?
C1 C2 O1 . . 110.7(3) ?
C1 C2 H2B . . 124.6 ?
O1 C2 H2B . . 124.6 ?
C3 C4 O1 . . 109.7(3) ?
C3 C4 C5 . . 130.8(3) ?
O1 C4 C5 . . 119.4(3) ?
C2 C1 C3 . . 106.6(3) ?
C2 C1 H1B . . 126.7 ?
C3 C1 H1B . . 126.7 ?
N3 C13 H13A . . 105(3) ?
N3 C13 H13B . . 111(3) ?
H13A C13 H13B . . 116(4) ?
N3 C13 H13C . . 112(4) ?
H13A C13 H13C . . 110(4) ?
H13B C13 H13C . . 103(5) ?
C4 C3 C1 . . 106.9(3) ?
C4 C3 H3A . . 126.6 ?
C1 C3 H3A . . 126.6 ?
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
N2 C5 . 1.352(4) ?
N2 N1 . 1.384(3) ?
N2 H2A . 0.8600 ?
N1 C6 . 1.283(3) ?
C9 C8 . 1.366(4) ?
C9 C10 . 1.393(4) ?
C9 H9A . 0.9300 ?
O2 C5 . 1.222(3) ?
C7 C8 . 1.384(4) ?
C7 C12 . 1.385(4) ?
C7 C6 . 1.448(4) ?
C10 C11 . 1.391(4) ?
C10 N3 . 1.385(3) ?
O1 C4 . 1.359(4) ?
O1 C2 . 1.363(4) ?
C12 C11 . 1.371(4) ?
C12 H12A . 0.9300 ?
C11 H11A . 0.9300 ?
C5 C4 . 1.447(4) ?
N3 C14 . 1.431(5) ?
N3 C13 . 1.441(5) ?
C6 H6A . 0.9300 ?
C14 H14A . 0.99(5) ?
C14 H14B . 0.95(5) ?
C14 H14C . 0.92(7) ?
C8 H8A . 0.9300 ?
C2 C1 . 1.317(5) ?
C2 H2B . 0.9300 ?
C4 C3 . 1.336(4) ?
C1 C3 . 1.410(5) ?
C1 H1B . 0.9300 ?
C13 H13A . 0.99(4) ?
C13 H13B . 0.92(5) ?
C13 H13C . 0.95(6) ?
C3 H3A . 0.9300 ?
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_665 0.86 2.10 2.933(3) 163.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5259079
