#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/87/2218780.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_2218780
loop_
_publ_author_name
'Fan, Zheng'
'Shan, Shang'
'Wang, Shan-Heng'
'Wang, Wen-Long'
_publ_section_title
;
 (E)-1-(3-Methoxyphenyl)ethanone 4-nitrophenylhydrazone
;
_journal_coeditor_code           OM2241
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1341
_journal_paper_doi               10.1107/S1600536808018618
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H15 N3 O3'
_chemical_formula_moiety         'C15 H15 N3 O3'
_chemical_formula_sum            'C15 H15 N3 O3'
_chemical_formula_weight         285.30
_chemical_name_systematic
;
(E)-1-(3-Methoxyphenyl)ethanone 4-nitrophenylhydrazone
;
_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                 96.332(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.2977(17)
_cell_length_b                   24.709(9)
_cell_length_c                   13.132(5)
_cell_measurement_reflns_used    4665
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     1386.0(9)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16470
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.65
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0487
_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)+(0.0685P)²+0.02P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                1643
_reflns_number_total             3014
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2241.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218780
_cod_database_fobs_code          2218780
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
N N1 0.2858(3) 0.59466(6) 0.29114(11) 0.0540(4) Uani d . 1
N N2 0.4535(3) 0.63991(6) 0.27160(11) 0.0573(4) Uani d . 1
H H2 0.4405 0.6533 0.2109 0.069 Uiso calc R 1
N N3 1.2264(4) 0.73954(7) 0.58666(13) 0.0656(5) Uani d . 1
O O1 -0.4958(3) 0.41329(6) 0.10899(10) 0.0775(5) Uani d . 1
O O2 1.2533(4) 0.71902(6) 0.67268(11) 0.0944(6) Uani d . 1
O O3 1.3617(4) 0.78225(6) 0.56823(11) 0.0865(5) Uani d . 1
C C1 -0.0634(4) 0.52365(7) 0.24122(12) 0.0507(5) Uani d . 1
C C2 -0.2090(4) 0.48991(7) 0.16601(13) 0.0563(5) Uani d . 1
H H2A -0.2011 0.4985 0.0974 0.068 Uiso calc R 1
C C3 -0.3663(4) 0.44357(8) 0.19125(13) 0.0574(5) Uani d . 1
C C4 -0.3852(5) 0.43034(8) 0.29148(15) 0.0680(6) Uani d . 1
H H4 -0.4900 0.3993 0.3087 0.082 Uiso calc R 1
C C5 -0.2442(5) 0.46436(9) 0.36672(14) 0.0775(7) Uani d . 1
H H5 -0.2576 0.4560 0.4351 0.093 Uiso calc R 1
C C6 -0.0856(5) 0.51000(8) 0.34328(14) 0.0669(6) Uani d . 1
H H6 0.0075 0.5319 0.3955 0.080 Uiso calc R 1
C C7 0.1106(4) 0.57271(7) 0.21575(13) 0.0528(5) Uani d . 1
C C8 0.0787(5) 0.59459(9) 0.10844(15) 0.0818(7) Uani d . 1
H H8A 0.0396 0.6328 0.1099 0.123 Uiso calc R 1
H H8B -0.0926 0.5769 0.0686 0.123 Uiso calc R 1
H H8C 0.2686 0.5880 0.0782 0.123 Uiso calc R 1
C C9 -0.6460(5) 0.36382(8) 0.13053(16) 0.0790(7) Uani d . 1
H H9A -0.5045 0.3419 0.1746 0.119 Uiso calc R 1
H H9B -0.7058 0.3448 0.0677 0.119 Uiso calc R 1
H H9C -0.8290 0.3715 0.1638 0.119 Uiso calc R 1
C C10 0.6430(4) 0.66358(7) 0.35048(13) 0.0488(4) Uani d . 1
C C11 0.6824(4) 0.64122(7) 0.44883(14) 0.0574(5) Uani d . 1
H H11 0.5794 0.6094 0.4625 0.069 Uiso calc R 1
C C12 0.8742(4) 0.66645(8) 0.52547(14) 0.0582(5) Uani d . 1
H H12 0.8993 0.6518 0.5911 0.070 Uiso calc R 1
C C13 1.0288(4) 0.71338(7) 0.50517(13) 0.0520(5) Uani d . 1
C C14 0.9974(4) 0.73569(7) 0.40765(14) 0.0566(5) Uani d . 1
H H14 1.1054 0.7670 0.3942 0.068 Uiso calc R 1
C C15 0.8043(4) 0.71083(7) 0.33116(14) 0.0564(5) Uani d . 1
H H15 0.7809 0.7257 0.2657 0.068 Uiso calc R 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 118.18(15)
N1 N2 C10 119.09(14)
N1 N2 H2 120.5
C10 N2 H2 120.5
O2 N3 O3 121.99(17)
O2 N3 C13 118.92(18)
O3 N3 C13 119.08(17)
C3 O1 C9 117.53(15)
C2 C1 C6 117.71(18)
C2 C1 C7 122.00(16)
C6 C1 C7 120.29(16)
C1 C2 C3 121.26(17)
C1 C2 H2A 119.4
C3 C2 H2A 119.4
C4 C3 O1 124.23(18)
C4 C3 C2 120.60(17)
O1 C3 C2 115.17(16)
C3 C4 C5 118.30(19)
C3 C4 H4 120.8
C5 C4 H4 120.8
C6 C5 C4 121.90(18)
C6 C5 H5 119.0
C4 C5 H5 119.0
C5 C6 C1 120.22(18)
C5 C6 H6 119.9
C1 C6 H6 119.9
N1 C7 C1 115.80(16)
N1 C7 C8 123.50(18)
C1 C7 C8 120.69(16)
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 H9A 109.5
O1 C9 H9B 109.5
H9A C9 H9B 109.5
O1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N2 C10 C15 118.92(16)
N2 C10 C11 121.93(16)
C15 C10 C11 119.14(16)
C12 C11 C10 119.85(17)
C12 C11 H11 120.1
C10 C11 H11 120.1
C13 C12 C11 120.15(17)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 120.89(16)
C12 C13 N3 119.38(17)
C14 C13 N3 119.73(18)
C15 C14 C13 119.09(18)
C15 C14 H14 120.5
C13 C14 H14 120.5
C14 C15 C10 120.86(17)
C14 C15 H15 119.6
C10 C15 H15 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.295(2)
N1 N2 1.3699(19)
N2 C10 1.376(2)
N2 H2 0.8600
N3 O2 1.232(2)
N3 O3 1.242(2)
N3 C13 1.443(2)
O1 C3 1.380(2)
O1 C9 1.425(2)
C1 C2 1.388(2)
C1 C6 1.395(2)
C1 C7 1.482(2)
C2 C3 1.388(2)
C2 H2A 0.9300
C3 C4 1.367(3)
C4 C5 1.385(3)
C4 H4 0.9300
C5 C6 1.370(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.501(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C15 1.395(2)
C10 C11 1.398(3)
C11 C12 1.378(2)
C11 H11 0.9300
C12 C13 1.377(3)
C12 H12 0.9300
C13 C14 1.387(2)
C14 C15 1.375(2)
C14 H14 0.9300
C15 H15 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
_geom_hbond_publ_flag
N2 H2 O3 4_475 0.86 2.45 3.279(2) 161 y
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 C10 -179.48(14)
C6 C1 C2 C3 -1.2(3)
C7 C1 C2 C3 178.84(16)
C9 O1 C3 C4 -3.0(3)
C9 O1 C3 C2 176.82(17)
C1 C2 C3 C4 0.9(3)
C1 C2 C3 O1 -178.98(16)
O1 C3 C4 C5 179.96(18)
C2 C3 C4 C5 0.1(3)
C3 C4 C5 C6 -0.7(3)
C4 C5 C6 C1 0.3(3)
C2 C1 C6 C5 0.7(3)
C7 C1 C6 C5 -179.42(18)
N2 N1 C7 C1 179.54(13)
N2 N1 C7 C8 -0.8(3)
C2 C1 C7 N1 -166.90(16)
C6 C1 C7 N1 13.2(2)
C2 C1 C7 C8 13.4(3)
C6 C1 C7 C8 -166.53(19)
N1 N2 C10 C15 -177.60(15)
N1 N2 C10 C11 3.4(2)
N2 C10 C11 C12 -179.86(15)
C15 C10 C11 C12 1.2(3)
C10 C11 C12 C13 -0.5(3)
C11 C12 C13 C14 -0.7(3)
C11 C12 C13 N3 179.40(16)
O2 N3 C13 C12 0.4(3)
O3 N3 C13 C12 -179.01(17)
O2 N3 C13 C14 -179.54(17)
O3 N3 C13 C14 1.1(3)
C12 C13 C14 C15 1.2(3)
N3 C13 C14 C15 -178.92(16)
C13 C14 C15 C10 -0.5(3)
N2 C10 C15 C14 -179.69(15)
C11 C10 C15 C14 -0.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 22920406
