#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/46/2224656.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_2224656
loop_
_publ_author_name
'Carvalho, Samir A.'
'da Silva, Edson F.'
'de Souza, Marcus V. N.'
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
_publ_section_title
;
 (2E)-N'-Benzoyl-3-(4-nitrophenyl)prop-2-enohydrazide
;
_journal_coeditor_code           HB5278
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o150
_journal_page_last               o151
_journal_paper_doi               10.1107/S1600536809053379
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H13 N3 O4'
_chemical_formula_moiety         'C16 H13 N3 O4'
_chemical_formula_sum            'C16 H13 N3 O4'
_chemical_formula_weight         311.29
_chemical_name_systematic
;
(2E)-N'-Benzoyl-3-(4-nitrophenyl)prop-2-enohydrazide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.535(2)
_cell_angle_beta                 102.701(2)
_cell_angle_gamma                91.728(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8263(2)
_cell_length_b                   9.6483(3)
_cell_length_c                   10.8571(3)
_cell_measurement_reflns_used    7821
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     693.35(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.035
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15199
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max_lt       0.001
_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+0.1871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.108
_refine_ls_wR_factor_ref         0.127
_reflns_number_gt                2495
_reflns_number_total             3157
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5278.cif
_cod_data_source_block           I
_cod_database_code               2224656
_cod_database_fobs_code          2224656
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 O1 -0.61174(17) 0.25925(13) 1.01283(12) 0.0338(3) Uani d . 1 . .
O O2 -0.39300(16) 0.42685(11) 1.10137(10) 0.0231(3) Uani d . 1 . .
O O3 0.30141(14) 0.06073(10) 0.52732(10) 0.0185(2) Uani d . 1 . .
O O4 0.68693(15) 0.44415(10) 0.44917(10) 0.0214(3) Uani d . 1 . .
N N1 -0.45702(18) 0.33067(13) 1.01817(12) 0.0203(3) Uani d . 1 . .
N N2 0.44535(17) 0.27625(12) 0.53463(11) 0.0154(3) Uani d D 1 . .
H H2N 0.444(2) 0.3677(10) 0.5437(15) 0.018 Uiso d D 1 . .
N N3 0.56991(17) 0.22492(12) 0.45712(11) 0.0155(3) Uani d D 1 . .
H H3N 0.585(2) 0.1348(10) 0.4560(15) 0.019 Uiso d D 1 . .
C C1 -0.1035(2) 0.22612(15) 0.75127(13) 0.0150(3) Uani d . 1 . .
C C2 -0.2558(2) 0.13309(15) 0.76568(13) 0.0180(3) Uani d . 1 . .
H H2 -0.2777 0.0448 0.7166 0.022 Uiso calc R 1 . .
C C3 -0.3753(2) 0.16829(16) 0.85096(14) 0.0204(3) Uani d . 1 . .
H H3 -0.4784 0.1048 0.8610 0.024 Uiso calc R 1 . .
C C4 -0.3414(2) 0.29731(15) 0.92086(13) 0.0169(3) Uani d . 1 . .
C C5 -0.1974(2) 0.39458(15) 0.90566(14) 0.0191(3) Uani d . 1 . .
H H5 -0.1808 0.4843 0.9523 0.023 Uiso calc R 1 . .
C C6 -0.0783(2) 0.35802(15) 0.82096(14) 0.0194(3) Uani d . 1 . .
H H6 0.0219 0.4232 0.8099 0.023 Uiso calc R 1 . .
C C7 0.0287(2) 0.17919(14) 0.66696(13) 0.0153(3) Uani d . 1 . .
H H7 0.0028 0.0869 0.6258 0.018 Uiso calc R 1 . .
C C8 0.1816(2) 0.25341(14) 0.64252(13) 0.0160(3) Uani d . 1 . .
H H8 0.2078 0.3484 0.6764 0.019 Uiso calc R 1 . .
C C9 0.3096(2) 0.18722(14) 0.56259(13) 0.0142(3) Uani d . 1 . .
C C10 0.6883(2) 0.31779(14) 0.41785(13) 0.0149(3) Uani d . 1 . .
C C11 0.8125(2) 0.25900(14) 0.33038(13) 0.0151(3) Uani d . 1 . .
C C12 0.9921(2) 0.33116(15) 0.32771(14) 0.0180(3) Uani d . 1 . .
H H12 1.0378 0.4122 0.3850 0.022 Uiso calc R 1 . .
C C13 1.1038(2) 0.28350(16) 0.24048(15) 0.0220(3) Uani d . 1 . .
H H13 1.2270 0.3312 0.2393 0.026 Uiso calc R 1 . .
C C14 1.0350(2) 0.16644(16) 0.15541(15) 0.0241(3) Uani d . 1 . .
H H14 1.1097 0.1358 0.0946 0.029 Uiso calc R 1 . .
C C15 0.8579(2) 0.09389(16) 0.15851(15) 0.0248(3) Uani d . 1 . .
H H15 0.8125 0.0130 0.1010 0.030 Uiso calc R 1 . .
C C16 0.7471(2) 0.14018(15) 0.24624(14) 0.0197(3) Uani d . 1 . .
H H16 0.6261 0.0904 0.2487 0.024 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 0.0016 '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
O2 N1 O1 . . 123.49(12) ?
O2 N1 C4 . . 118.41(11) ?
O1 N1 C4 . . 118.09(12) ?
C9 N2 N3 . . 118.46(11) ?
C9 N2 H2N . . 125.6(11) ?
N3 N2 H2N . . 114.0(11) ?
C10 N3 N2 . . 117.73(11) ?
C10 N3 H3N . . 126.1(11) ?
N2 N3 H3N . . 114.1(11) ?
C2 C1 C6 . . 118.84(12) ?
C2 C1 C7 . . 118.38(13) ?
C6 C1 C7 . . 122.74(12) ?
C3 C2 C1 . . 120.74(13) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C4 C3 C2 . . 118.63(13) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 122.36(13) ?
C3 C4 N1 . . 118.74(12) ?
C5 C4 N1 . . 118.87(13) ?
C6 C5 C4 . . 118.45(13) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
C5 C6 C1 . . 120.90(13) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
C8 C7 C1 . . 126.49(13) ?
C8 C7 H7 . . 116.8 ?
C1 C7 H7 . . 116.8 ?
C7 C8 C9 . . 119.74(13) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
O3 C9 N2 . . 121.75(12) ?
O3 C9 C8 . . 124.24(12) ?
N2 C9 C8 . . 113.95(12) ?
O4 C10 N3 . . 121.47(12) ?
O4 C10 C11 . . 122.51(12) ?
N3 C10 C11 . . 115.96(12) ?
C16 C11 C12 . . 119.75(13) ?
C16 C11 C10 . . 121.48(12) ?
C12 C11 C10 . . 118.62(13) ?
C13 C12 C11 . . 119.66(14) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C14 C13 C12 . . 120.04(14) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C15 . . 120.45(13) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C14 C15 C16 . . 119.70(14) ?
C14 C15 H15 . . 120.2 ?
C16 C15 H15 . . 120.2 ?
C15 C16 C11 . . 120.37(13) ?
C15 C16 H16 . . 119.8 ?
C11 C16 H16 . . 119.8 ?
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
O1 N1 . 1.2309(16) ?
O2 N1 . 1.2282(16) ?
O3 C9 . 1.2392(16) ?
O4 C10 . 1.2346(16) ?
N1 C4 . 1.4695(17) ?
N2 C9 . 1.3469(17) ?
N2 N3 . 1.3914(16) ?
N2 H2N . 0.879(9) ?
N3 C10 . 1.3490(18) ?
N3 H3N . 0.878(9) ?
C1 C2 . 1.3974(19) ?
C1 C6 . 1.402(2) ?
C1 C7 . 1.4717(18) ?
C2 C3 . 1.3884(19) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.379(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.386(2) ?
C5 C6 . 1.3834(19) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.3360(19) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.4784(18) ?
C8 H8 . 0.9500 ?
C10 C11 . 1.4905(18) ?
C11 C16 . 1.3913(19) ?
C11 C12 . 1.399(2) ?
C12 C13 . 1.394(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.388(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.387(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.391(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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 H2n O4 1_555 0.879(10) 2.273(14) 2.6470(16) 105.5(11)
N2 H2n O4 2_666 0.879(10) 2.050(11) 2.8721(15) 155.4(13)
N3 H3n O3 1_555 0.878(10) 2.354(14) 2.6687(15) 101.3(10)
N3 H3n O3 2_656 0.878(10) 2.070(11) 2.9269(15) 165.0(13)
C12 H12 O4 2_766 0.95 2.56 3.4257(18) 151
C14 H14 O1 1_754 0.95 2.58 3.2851(19) 132
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N2 N3 C10 . . . . 172.40(12) ?
C6 C1 C2 C3 . . . . -2.4(2) ?
C7 C1 C2 C3 . . . . 175.31(13) ?
C1 C2 C3 C4 . . . . 0.3(2) ?
C2 C3 C4 C5 . . . . 2.4(2) ?
C2 C3 C4 N1 . . . . -175.32(13) ?
O2 N1 C4 C3 . . . . 161.15(13) ?
O1 N1 C4 C3 . . . . -17.9(2) ?
O2 N1 C4 C5 . . . . -16.63(19) ?
O1 N1 C4 C5 . . . . 164.35(13) ?
C3 C4 C5 C6 . . . . -2.8(2) ?
N1 C4 C5 C6 . . . . 174.94(12) ?
C4 C5 C6 C1 . . . . 0.5(2) ?
C2 C1 C6 C5 . . . . 2.0(2) ?
C7 C1 C6 C5 . . . . -175.60(13) ?
C2 C1 C7 C8 . . . . -179.69(13) ?
C6 C1 C7 C8 . . . . -2.1(2) ?
C1 C7 C8 C9 . . . . 175.50(12) ?
N3 N2 C9 O3 . . . . 4.2(2) ?
N3 N2 C9 C8 . . . . -178.39(11) ?
C7 C8 C9 O3 . . . . -9.0(2) ?
C7 C8 C9 N2 . . . . 173.72(12) ?
N2 N3 C10 O4 . . . . 0.0(2) ?
N2 N3 C10 C11 . . . . -177.37(11) ?
O4 C10 C11 C16 . . . . -146.43(14) ?
N3 C10 C11 C16 . . . . 30.87(19) ?
O4 C10 C11 C12 . . . . 29.2(2) ?
N3 C10 C11 C12 . . . . -153.50(13) ?
C16 C11 C12 C13 . . . . 0.1(2) ?
C10 C11 C12 C13 . . . . -175.56(12) ?
C11 C12 C13 C14 . . . . 1.1(2) ?
C12 C13 C14 C15 . . . . -1.7(2) ?
C13 C14 C15 C16 . . . . 1.0(2) ?
C14 C15 C16 C11 . . . . 0.3(2) ?
C12 C11 C16 C15 . . . . -0.8(2) ?
C10 C11 C16 C15 . . . . 174.75(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20699680
