#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/40/2214023.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_2214023
loop_
_publ_author_name
'Huan-Mei Guo'
_publ_section_title
;
 N'-(1-Phenylethylidene)acetohydrazide
;
_journal_coeditor_code           AT2312
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3123
_journal_page_last               o3123
_journal_paper_doi               10.1107/S1600536807026748
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H12 N2 O'
_chemical_formula_moiety         'C10 H12 N2 O'
_chemical_formula_sum            'C10 H12 N2 O'
_chemical_formula_weight         176.22
_chemical_name_systematic
;
N'-(1-Phenylethylidene)acetohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 95.496(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3681(18)
_cell_length_b                   9.361(3)
_cell_length_c                   19.033(6)
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.15
_cell_volume                     952.0(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0698
_diffrn_reflns_av_sigmaI/netI    0.0885
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5285
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9791
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.143
_refine_ls_extinction_coef       0.067(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0485
_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)+(0.0397P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                882
_reflns_number_total             1940
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2312.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214023
_cod_database_fobs_code          2214023
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
O O1 1.4564(3) 0.56158(18) 0.58573(8) 0.0711(6) Uani d . 1
N N1 1.0181(3) 0.72134(19) 0.46283(10) 0.0492(5) Uani d . 1
N N2 1.2145(4) 0.6349(2) 0.48995(10) 0.0527(6) Uani d D 1
C C1 0.5972(4) 0.8765(2) 0.41812(12) 0.0505(7) Uani d . 1
H H1 0.6218 0.8495 0.4653 0.061 Uiso calc R 1
C C2 0.4048(5) 0.9687(3) 0.39673(12) 0.0586(7) Uani d . 1
H H2 0.3014 1.0030 0.4294 0.070 Uiso calc R 1
C C3 0.3650(5) 1.0105(3) 0.32713(14) 0.0616(8) Uani d . 1
H H3 0.2363 1.0736 0.3128 0.074 Uiso calc R 1
C C4 0.5168(5) 0.9580(3) 0.27914(13) 0.0611(7) Uani d . 1
H H4 0.4898 0.9851 0.2320 0.073 Uiso calc R 1
C C5 0.7111(4) 0.8644(2) 0.30053(12) 0.0560(7) Uani d . 1
H H5 0.8125 0.8294 0.2675 0.067 Uiso calc R 1
C C6 0.7554(4) 0.8228(2) 0.37083(11) 0.0431(6) Uani d . 1
C C7 0.9639(4) 0.7243(2) 0.39541(12) 0.0463(6) Uani d . 1
C C8 1.0931(5) 0.6416(2) 0.34212(12) 0.0623(8) Uani d . 1
H H8A 1.2002 0.7043 0.3188 0.093 Uiso calc R 1
H H8B 0.9704 0.6006 0.3080 0.093 Uiso calc R 1
H H8C 1.1915 0.5668 0.3655 0.093 Uiso calc R 1
C C9 1.2788(5) 0.6354(3) 0.56074(13) 0.0528(7) Uani d . 1
C C10 1.1281(5) 0.7261(3) 0.60558(12) 0.0659(8) Uani d . 1
H H10A 1.1863 0.7125 0.6544 0.099 Uiso calc R 1
H H10B 0.9550 0.6994 0.5979 0.099 Uiso calc R 1
H H10C 1.1462 0.8248 0.5932 0.099 Uiso calc R 1
H H2A 1.302(4) 0.576(2) 0.4637(10) 0.070(9) Uiso d 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
O1 0.0738(13) 0.0854(13) 0.0519(11) 0.0266(11) -0.0058(10) 0.0042(9)
N1 0.0445(12) 0.0578(12) 0.0446(12) -0.0008(10) -0.0001(10) 0.0073(10)
N2 0.0549(14) 0.0599(14) 0.0423(13) 0.0097(12) -0.0002(11) 0.0043(11)
C1 0.0533(16) 0.0593(15) 0.0381(14) -0.0005(13) 0.0000(12) 0.0051(12)
C2 0.0571(17) 0.0710(18) 0.0472(16) 0.0068(15) 0.0029(13) -0.0075(13)
C3 0.0572(18) 0.0659(18) 0.0598(18) 0.0079(14) -0.0053(15) 0.0019(14)
C4 0.0628(19) 0.0726(18) 0.0464(16) -0.0014(15) -0.0031(15) 0.0140(14)
C5 0.0569(17) 0.0689(17) 0.0421(15) -0.0012(14) 0.0039(12) 0.0026(13)
C6 0.0434(14) 0.0492(15) 0.0362(13) -0.0071(12) 0.0011(11) 0.0000(11)
C7 0.0466(15) 0.0484(14) 0.0433(14) -0.0056(12) 0.0016(12) -0.0015(12)
C8 0.0690(18) 0.0666(16) 0.0499(15) 0.0078(14) -0.0017(13) -0.0038(13)
C9 0.0566(17) 0.0555(16) 0.0460(16) -0.0005(14) 0.0032(13) 0.0029(13)
C10 0.0755(19) 0.0724(18) 0.0489(15) 0.0095(15) 0.0013(14) -0.0001(13)
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
C7 N1 N2 118.3(2)
C9 N2 N1 118.6(2)
C9 N2 H2A 117.1(14)
N1 N2 H2A 124.3(14)
C2 C1 C6 121.5(2)
C2 C1 H1 119.2
C6 C1 H1 119.2
C1 C2 C3 120.3(2)
C1 C2 H2 119.8
C3 C2 H2 119.8
C4 C3 C2 119.4(2)
C4 C3 H3 120.3
C2 C3 H3 120.3
C3 C4 C5 120.4(2)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 120.8(2)
C6 C5 H5 119.6
C4 C5 H5 119.6
C1 C6 C5 117.6(2)
C1 C6 C7 120.5(2)
C5 C6 C7 121.9(2)
N1 C7 C6 114.7(2)
N1 C7 C8 126.0(2)
C6 C7 C8 119.32(19)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O1 C9 N2 119.6(2)
O1 C9 C10 122.5(2)
N2 C9 C10 117.9(2)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.235(3)
N1 C7 1.289(2)
N1 N2 1.389(2)
N2 C9 1.358(3)
N2 H2A 0.904(10)
C1 C2 1.378(3)
C1 C6 1.389(3)
C1 H1 0.9300
C2 C3 1.378(3)
C2 H2 0.9300
C3 C4 1.372(3)
C3 H3 0.9300
C4 C5 1.393(3)
C4 H4 0.9300
C5 C6 1.392(3)
C5 H5 0.9300
C6 C7 1.490(3)
C7 C8 1.498(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.496(3)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 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
_geom_hbond_publ_flag
N2 H2A O1 3_866 0.91(2) 2.11(2) 3.011(3) 172.2(18) yes
C8 H8C N2 . 0.96 2.44 2.827(3) 103 yes
C8 H8C O1 3_866 0.96 2.35 3.273(3) 160 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
C7 N1 N2 C9 177.5(2)
C6 C1 C2 C3 -0.1(3)
C1 C2 C3 C4 0.7(3)
C2 C3 C4 C5 -0.6(4)
C3 C4 C5 C6 -0.2(3)
C2 C1 C6 C5 -0.6(3)
C2 C1 C6 C7 179.33(19)
C4 C5 C6 C1 0.8(3)
C4 C5 C6 C7 -179.2(2)
N2 N1 C7 C6 -178.45(18)
N2 N1 C7 C8 0.4(3)
C1 C6 C7 N1 -15.2(3)
C5 C6 C7 N1 164.71(19)
C1 C6 C7 C8 165.8(2)
C5 C6 C7 C8 -14.2(3)
N1 N2 C9 O1 -178.5(2)
N1 N2 C9 C10 1.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4546287
