#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/20/2232049.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_2232049
loop_
_publ_author_name
'Zeb, A.'
'Yousuf, S.'
_publ_section_title
;
 (E)-1-(3-Nitrophenyl)ethanone (2-methylphenyl)hydrazone
;
_journal_coeditor_code           RZ2637
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2801
_journal_paper_doi               10.1107/S1600536811037846
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H15 N3 O2'
_chemical_formula_moiety         'C15 H15 N3 O2'
_chemical_formula_sum            'C15 H15 N3 O2'
_chemical_formula_weight         269.30
_chemical_name_systematic
;
(E)-1-(3-Nitrophenyl)ethanone (2-methylphenyl)hydrazone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 110.485(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4763(18)
_cell_length_b                   25.742(6)
_cell_length_c                   7.6564(19)
_cell_measurement_reflns_used    2070
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.36
_cell_measurement_theta_min      2.95
_cell_volume                     1380.3(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7958
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0602
_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)+(0.0991P)²+0.0824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1758
_reflns_number_gt                1746
_reflns_number_total             2535
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2637.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2232049
_cod_database_fobs_code          2232049
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
O O1 -0.0105(4) 0.25761(8) 0.7851(3) 0.1120(8) Uani d . 1 1
O O2 -0.0998(3) 0.30826(7) 0.5495(3) 0.0983(6) Uani d . 1 1
N N1 0.2485(3) 0.00558(7) 0.5057(3) 0.0652(5) Uani d . 1 1
N N2 0.1857(2) 0.05385(7) 0.4420(2) 0.0600(5) Uani d . 1 1
N N3 -0.0373(3) 0.26679(8) 0.6232(3) 0.0753(6) Uani d . 1 1
C C1 0.0995(4) 0.15320(9) 0.3011(3) 0.0716(6) Uani d . 1 1
H H1B 0.1320 0.1284 0.2290 0.086 Uiso calc R 1 1
C C2 0.0380(4) 0.20121(10) 0.2255(3) 0.0780(7) Uani d . 1 1
H H2B 0.0275 0.2082 0.1032 0.094 Uiso calc R 1 1
C C3 -0.0082(3) 0.23888(9) 0.3293(3) 0.0705(6) Uani d . 1 1
H H3A -0.0495 0.2716 0.2797 0.085 Uiso calc R 1 1
C C4 0.0086(3) 0.22673(8) 0.5084(3) 0.0603(5) Uani d . 1 1
C C5 0.0684(3) 0.17883(8) 0.5874(3) 0.0581(5) Uani d . 1 1
H H5A 0.0778 0.1722 0.7097 0.070 Uiso calc R 1 1
C C6 0.1147(3) 0.14059(8) 0.4826(3) 0.0557(5) Uani d . 1 1
C C7 0.1796(3) 0.08832(8) 0.5615(3) 0.0548(5) Uani d . 1 1
C C8 0.3256(3) -0.08197(8) 0.4538(3) 0.0619(6) Uani d . 1 1
C C9 0.3307(3) -0.12021(9) 0.3286(4) 0.0759(7) Uani d . 1 1
H H9A 0.3731 -0.1533 0.3731 0.091 Uiso calc R 1 1
C C10 0.2748(4) -0.11080(11) 0.1401(4) 0.0856(8) Uani d . 1 1
H H10A 0.2791 -0.1372 0.0588 0.103 Uiso calc R 1 1
C C11 0.2130(4) -0.06233(11) 0.0734(3) 0.0821(7) Uani d . 1 1
H H11A 0.1747 -0.0558 -0.0539 0.099 Uiso calc R 1 1
C C12 0.2068(3) -0.02331(9) 0.1923(3) 0.0691(6) Uani d . 1 1
H H12A 0.1665 0.0097 0.1456 0.083 Uiso calc R 1 1
C C13 0.2604(3) -0.03265(8) 0.3823(3) 0.0576(5) Uani d . 1 1
C C14 0.3872(4) -0.09290(10) 0.6573(3) 0.0836(7) Uani d . 1 1
H H14A 0.4376 -0.1275 0.6814 0.125 Uiso calc R 1 1
H H14B 0.2796 -0.0898 0.6976 0.125 Uiso calc R 1 1
H H14C 0.4840 -0.0685 0.7242 0.125 Uiso calc R 1 1
C C15 0.2345(4) 0.07845(9) 0.7658(3) 0.0728(6) Uani d . 1 1
H H15A 0.3563 0.0614 0.8110 0.109 Uiso calc R 1 1
H H15B 0.1401 0.0567 0.7877 0.109 Uiso calc R 1 1
H H15C 0.2422 0.1109 0.8299 0.109 Uiso calc R 1 1
H H1N1 0.285(4) -0.0027(9) 0.622(4) 0.079(8) Uiso d . 1 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
N2 N1 C13 120.06(18)
N2 N1 H1N1 122.9(16)
C13 N1 H1N1 117.0(16)
C7 N2 N1 118.04(17)
O1 N3 O2 123.0(2)
O1 N3 C4 119.10(19)
O2 N3 C4 117.9(2)
C2 C1 C6 121.9(2)
C2 C1 H1B 119.1
C6 C1 H1B 119.1
C3 C2 C1 120.5(2)
C3 C2 H2B 119.8
C1 C2 H2B 119.8
C4 C3 C2 117.7(2)
C4 C3 H3A 121.1
C2 C3 H3A 121.1
C3 C4 C5 123.11(19)
C3 C4 N3 118.66(19)
C5 C4 N3 118.24(19)
C4 C5 C6 119.32(19)
C4 C5 H5A 120.3
C6 C5 H5A 120.3
C5 C6 C1 117.51(19)
C5 C6 C7 121.31(18)
C1 C6 C7 121.17(18)
N2 C7 C6 115.08(17)
N2 C7 C15 124.21(18)
C6 C7 C15 120.72(17)
C9 C8 C13 117.6(2)
C9 C8 C14 121.1(2)
C13 C8 C14 121.22(19)
C10 C9 C8 122.0(2)
C10 C9 H9A 119.0
C8 C9 H9A 119.0
C11 C10 C9 119.4(2)
C11 C10 H10A 120.3
C9 C10 H10A 120.3
C10 C11 C12 120.6(2)
C10 C11 H11A 119.7
C12 C11 H11A 119.7
C11 C12 C13 120.4(2)
C11 C12 H12A 119.8
C13 C12 H12A 119.8
C12 C13 N1 121.79(19)
C12 C13 C8 120.01(19)
N1 C13 C8 118.19(19)
C8 C14 H14A 109.5
C8 C14 H14B 109.5
H14A C14 H14B 109.5
C8 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 C15 H15A 109.5
C7 C15 H15B 109.5
H15A C15 H15B 109.5
C7 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.207(2)
O2 N3 1.222(2)
N1 N2 1.357(2)
N1 C13 1.389(3)
N1 H1N1 0.86(2)
N2 C7 1.286(2)
N3 C4 1.471(3)
C1 C2 1.374(3)
C1 C6 1.392(3)
C1 H1B 0.9300
C2 C3 1.372(3)
C2 H2B 0.9300
C3 C4 1.369(3)
C3 H3A 0.9300
C4 C5 1.377(3)
C5 C6 1.388(3)
C5 H5A 0.9300
C6 C7 1.485(3)
C7 C15 1.493(3)
C8 C9 1.384(3)
C8 C13 1.401(3)
C8 C14 1.489(3)
C9 C10 1.376(3)
C9 H9A 0.9300
C10 C11 1.366(4)
C10 H10A 0.9300
C11 C12 1.367(3)
C11 H11A 0.9300
C12 C13 1.388(3)
C12 H12A 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
C13 N1 N2 C7 -178.96(16)
C6 C1 C2 C3 1.0(4)
C1 C2 C3 C4 -0.3(4)
C2 C3 C4 C5 -0.2(3)
C2 C3 C4 N3 179.1(2)
O1 N3 C4 C3 -175.0(2)
O2 N3 C4 C3 4.4(3)
O1 N3 C4 C5 4.4(3)
O2 N3 C4 C5 -176.2(2)
C3 C4 C5 C6 0.1(3)
N3 C4 C5 C6 -179.27(18)
C4 C5 C6 C1 0.6(3)
C4 C5 C6 C7 -179.92(18)
C2 C1 C6 C5 -1.2(3)
C2 C1 C6 C7 179.4(2)
N1 N2 C7 C6 178.38(16)
N1 N2 C7 C15 -1.0(3)
C5 C6 C7 N2 168.33(17)
C1 C6 C7 N2 -12.2(3)
C5 C6 C7 C15 -12.3(3)
C1 C6 C7 C15 167.1(2)
C13 C8 C9 C10 0.2(3)
C14 C8 C9 C10 -179.8(2)
C8 C9 C10 C11 0.2(4)
C9 C10 C11 C12 0.2(4)
C10 C11 C12 C13 -1.1(4)
C11 C12 C13 N1 -177.4(2)
C11 C12 C13 C8 1.6(3)
N2 N1 C13 C12 -1.0(3)
N2 N1 C13 C8 -179.92(17)
C9 C8 C13 C12 -1.1(3)
C14 C8 C13 C12 179.0(2)
C9 C8 C13 N1 177.85(18)
C14 C8 C13 N1 -2.1(3)
