##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#                                                                            #
# This file may be used for bona fide research purposes within the           #
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data_global
_audit_creation_method     'from SHELXL-97 with Word-Perfect Macro PRPKAPPA'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-10-05
_journal_date_accepted     2009-10-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     11
_journal_page_first     o2729
_journal_page_last     o2729
_journal_paper_category     QO
_journal_coeditor_code     HB5130
_publ_contact_author_name     'Low, John Nicolson'
_publ_contact_author_address
;
Department of Chemistry, University of Aberdeen,
Meston Walk, Old Aberdeen, AB24 3UE, Scotland.
;
_publ_contact_author_email     'jnlow111@googlemail.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone      441382542709
_publ_section_title
;
(E)-1-Phenylbutan-2-one (2,4-dinitrophenyl)hydrazone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Lima, Carlos F. R. A. C.' .
;
Centro de Investigação em Química,
Departamento de Química, Faculdade de Ciências,
Universidade do Porto
Rua do Campo Alegre, 687,
P-4169_007 Porto
Portugal
;
    'Gomes, Ligia R.' .
;
REQUIMTE,
Departamento de Química, Faculdade de Ciências,
Universidade do Porto
Rua do Campo Alegre, 687,
P-4169_007 Porto
Portugal
;
    'Santos, Luís M. N. B. F.' .
;
Centro de Investigação em Química,
Departamento de Química, Faculdade de Ciências,
Universidade do Porto
Rua do Campo Alegre, 687,
P-4169_007 Porto
Portugal
;
    'Rodriguez-Borges, José E.' .
;
Centro de Investigação em Química,
Departamento de Química, Faculdade de Ciências,
Universidade do Porto
Rua do Campo Alegre, 687,
P-4169_007 Porto
Portugal
;
    'Low, John Nicolson' .
;
Department of Chemistry, University of Aberdeen,
Meston Walk, Old Aberdeen AB24 3UE, Scotland.
;
data_I
_chemical_name_systematic
;
(E)-1-Phenylbutan-2-one (2,4-dinitrophenyl)hydrazone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 N4 O4'
_chemical_formula_sum     'C16 H16 N4 O4'
_chemical_formula_iupac     'C16 H16 N4 O4'
_chemical_formula_weight     328.33
_chemical_melting_point     'not measured'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     15.8919(13)
_cell_length_b     4.9446(3)
_cell_length_c     20.7397(17)
_cell_angle_alpha     90.00
_cell_angle_beta     105.267(5)
_cell_angle_gamma     90.00
_cell_volume     1572.2(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2030
_cell_measurement_theta_min     3.09
_cell_measurement_theta_max     26.5
_cell_measurement_temperature     120(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.387
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     0.102
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2004)'
_exptl_absorpt_correction_T_min     0.970
_exptl_absorpt_correction_T_max     0.998
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.333
_diffrn_reflns_number     14305
_diffrn_reflns_av_R_equivalents     0.0478
_diffrn_reflns_av_sigmaI/netI     0.0487
_diffrn_reflns_theta_min     1.45
_diffrn_reflns_theta_max     27.28
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3531
_reflns_number_gt     2418
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0760
_refine_ls_R_factor_gt     0.0413
_refine_ls_wR_factor_gt     0.0857
_refine_ls_wR_factor_ref     0.1005
_refine_ls_goodness_of_fit_ref     1.009
_refine_ls_restrained_S_all     1.010
_refine_ls_number_reflns     3531
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.037P)²+0.4505P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.251
_refine_diff_density_min     -0.193
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0044(11)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'APEX2 and SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                               'ORTEPII (Johnson, 1976) and PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 O121 0.65610(8) 0.8996(2) 0.17034(6) 0.0325(3) Uani d . 1 . .
    O O122 0.70928(7) 0.9899(2) 0.27500(6) 0.0276(3) Uani d . 1 . .
    O O141 0.44704(9) 0.2157(3) 0.09414(6) 0.0454(4) Uani d . 1 . .
    O O142 0.41347(8) -0.0583(3) 0.16477(7) 0.0427(4) Uani d . 1 . .
    N N1 0.66460(8) 0.7090(3) 0.36646(6) 0.0225(3) Uani d D 1 . .
    H H1 0.6995 0.8261 0.3582 0.027 Uiso d RD 1 . .
    N N2 0.66485(9) 0.6313(3) 0.43054(6) 0.0225(3) Uani d . 1 . .
    N N12 0.66156(9) 0.8554(3) 0.22955(7) 0.0225(3) Uani d . 1 . .
    N N14 0.45198(9) 0.1408(3) 0.15136(7) 0.0301(3) Uani d . 1 . .
    C C2 0.71757(10) 0.7597(3) 0.47833(8) 0.0220(3) Uani d . 1 . .
    C C3 0.71901(11) 0.6653(3) 0.54758(8) 0.0250(4) Uani d . 1 . .
    H H3A 0.7789 0.6066 0.5708 0.030 Uiso calc R 1 . .
    H H3B 0.6800 0.5068 0.5442 0.030 Uiso calc R 1 . .
    C C11 0.61365(10) 0.5756(3) 0.31389(7) 0.0195(3) Uani d . 1 . .
    C C12 0.61004(10) 0.6396(3) 0.24669(8) 0.0194(3) Uani d . 1 . .
    C C13 0.55682(10) 0.4984(3) 0.19381(8) 0.0228(4) Uani d . 1 . .
    H H13 0.5557 0.5436 0.1491 0.027 Uiso calc R 1 . .
    C C14 0.50597(10) 0.2934(3) 0.20667(8) 0.0227(4) Uani d . 1 . .
    C C15 0.50676(10) 0.2231(3) 0.27206(8) 0.0235(4) Uani d . 1 . .
    H H15 0.4710 0.0798 0.2801 0.028 Uiso calc R 1 . .
    C C16 0.55915(10) 0.3614(3) 0.32419(8) 0.0223(4) Uani d . 1 . .
    H H16 0.5592 0.3133 0.3686 0.027 Uiso calc R 1 . .
    C C21 0.77979(11) 0.9796(3) 0.47154(8) 0.0269(4) Uani d . 1 . .
    H H21A 0.7905 1.0997 0.5111 0.032 Uiso calc R 1 . .
    H H21B 0.7532 1.0896 0.4315 0.032 Uiso calc R 1 . .
    C C22 0.86642(12) 0.8638(4) 0.46542(10) 0.0410(5) Uani d . 1 . .
    H H22A 0.9053 1.0120 0.4607 0.061 Uiso calc R 1 . .
    H H22B 0.8560 0.7461 0.4261 0.061 Uiso calc R 1 . .
    H H22C 0.8936 0.7587 0.5056 0.061 Uiso calc R 1 . .
    C C31 0.69053(11) 0.8820(3) 0.58860(8) 0.0228(4) Uani d . 1 . .
    C C32 0.74933(11) 1.0031(3) 0.64209(8) 0.0257(4) Uani d . 1 . .
    H H32 0.8088 0.9494 0.6534 0.031 Uiso calc R 1 . .
    C C33 0.72226(12) 1.2021(3) 0.67932(8) 0.0300(4) Uani d . 1 . .
    H H33 0.7633 1.2831 0.7160 0.036 Uiso calc R 1 . .
    C C34 0.63628(12) 1.2830(4) 0.66341(9) 0.0317(4) Uani d . 1 . .
    H H34 0.6179 1.4195 0.6890 0.038 Uiso calc R 1 . .
    C C35 0.57701(12) 1.1645(4) 0.61015(9) 0.0332(4) Uani d . 1 . .
    H H35 0.5177 1.2198 0.5989 0.040 Uiso calc R 1 . .
    C C36 0.60383(11) 0.9647(4) 0.57296(9) 0.0300(4) Uani d . 1 . .
    H H36 0.5626 0.8836 0.5365 0.036 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    O121 N12 . 1.2276(16) ?
    O122 N12 . 1.2370(17) ?
    O141 N14 . 1.2258(18) ?
    O142 N14 . 1.2292(19) ?
    N1 C11 . 1.3469(19) ?
    N1 N2 . 1.3823(17) ?
    N1 H1 . 0.85 ?
    N2 C2 . 1.284(2) ?
    N12 C12 . 1.445(2) ?
    N14 C14 . 1.450(2) ?
    C2 C21 . 1.501(2) ?
    C2 C3 . 1.505(2) ?
    C3 C31 . 1.510(2) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C11 C12 . 1.416(2) ?
    C11 C16 . 1.420(2) ?
    C12 C13 . 1.385(2) ?
    C13 C14 . 1.366(2) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.397(2) ?
    C15 C16 . 1.362(2) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C21 C22 . 1.527(2) ?
    C21 H21A . 0.9900 ?
    C21 H21B . 0.9900 ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    C31 C32 . 1.385(2) ?
    C31 C36 . 1.391(2) ?
    C32 C33 . 1.387(2) ?
    C32 H32 . 0.9500 ?
    C33 C34 . 1.378(2) ?
    C33 H33 . 0.9500 ?
    C34 C35 . 1.379(3) ?
    C34 H34 . 0.9500 ?
    C35 C36 . 1.388(2) ?
    C35 H35 . 0.9500 ?
    C36 H36 . 0.9500 ?
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
    C11 N1 N2 . . 119.42(13) ?
    C11 N1 H1 . . 117.1 ?
    N2 N1 H1 . . 123.1 ?
    C2 N2 N1 . . 116.15(13) ?
    O121 N12 O122 . . 122.28(13) ?
    O121 N12 C12 . . 118.84(13) ?
    O122 N12 C12 . . 118.88(13) ?
    O141 N14 O142 . . 123.53(15) ?
    O141 N14 C14 . . 118.82(15) ?
    O142 N14 C14 . . 117.64(15) ?
    N2 C2 C21 . . 126.70(14) ?
    N2 C2 C3 . . 115.22(14) ?
    C21 C2 C3 . . 117.99(14) ?
    C2 C3 C31 . . 112.72(13) ?
    C2 C3 H3A . . 109.0 ?
    C31 C3 H3A . . 109.0 ?
    C2 C3 H3B . . 109.0 ?
    C31 C3 H3B . . 109.0 ?
    H3A C3 H3B . . 107.8 ?
    N1 C11 C12 . . 123.19(14) ?
    N1 C11 C16 . . 120.26(14) ?
    C12 C11 C16 . . 116.54(14) ?
    C13 C12 C11 . . 121.67(14) ?
    C13 C12 N12 . . 116.42(14) ?
    C11 C12 N12 . . 121.91(14) ?
    C14 C13 C12 . . 119.28(15) ?
    C14 C13 H13 . . 120.4 ?
    C12 C13 H13 . . 120.4 ?
    C13 C14 C15 . . 121.32(15) ?
    C13 C14 N14 . . 119.28(15) ?
    C15 C14 N14 . . 119.38(15) ?
    C16 C15 C14 . . 119.54(15) ?
    C16 C15 H15 . . 120.2 ?
    C14 C15 H15 . . 120.2 ?
    C15 C16 C11 . . 121.65(15) ?
    C15 C16 H16 . . 119.2 ?
    C11 C16 H16 . . 119.2 ?
    C2 C21 C22 . . 111.49(14) ?
    C2 C21 H21A . . 109.3 ?
    C22 C21 H21A . . 109.3 ?
    C2 C21 H21B . . 109.3 ?
    C22 C21 H21B . . 109.3 ?
    H21A C21 H21B . . 108.0 ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C32 C31 C36 . . 118.53(15) ?
    C32 C31 C3 . . 121.28(15) ?
    C36 C31 C3 . . 120.19(15) ?
    C31 C32 C33 . . 120.67(16) ?
    C31 C32 H32 . . 119.7 ?
    C33 C32 H32 . . 119.7 ?
    C34 C33 C32 . . 120.39(17) ?
    C34 C33 H33 . . 119.8 ?
    C32 C33 H33 . . 119.8 ?
    C33 C34 C35 . . 119.58(16) ?
    C33 C34 H34 . . 120.2 ?
    C35 C34 H34 . . 120.2 ?
    C34 C35 C36 . . 120.17(17) ?
    C34 C35 H35 . . 119.9 ?
    C36 C35 H35 . . 119.9 ?
    C35 C36 C31 . . 120.67(17) ?
    C35 C36 H36 . . 119.7 ?
    C31 C36 H36 . . 119.7 ?
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
    C11 N1 N2 C2 . . . . 177.22(14) ?
    N1 N2 C2 C21 . . . . -1.4(2) ?
    N1 N2 C2 C3 . . . . -177.96(12) ?
    N2 C2 C3 C31 . . . . -117.81(16) ?
    C21 C2 C3 C31 . . . . 65.32(19) ?
    N2 N1 C11 C12 . . . . -179.33(13) ?
    N2 N1 C11 C16 . . . . 1.5(2) ?
    N1 C11 C12 C13 . . . . -179.94(14) ?
    C16 C11 C12 C13 . . . . -0.7(2) ?
    N1 C11 C12 N12 . . . . 0.1(2) ?
    C16 C11 C12 N12 . . . . 179.29(13) ?
    O121 N12 C12 C13 . . . . -0.6(2) ?
    O122 N12 C12 C13 . . . . 179.04(13) ?
    O121 N12 C12 C11 . . . . 179.42(14) ?
    O122 N12 C12 C11 . . . . -1.0(2) ?
    C11 C12 C13 C14 . . . . 0.5(2) ?
    N12 C12 C13 C14 . . . . -179.50(13) ?
    C12 C13 C14 C15 . . . . -0.2(2) ?
    C12 C13 C14 N14 . . . . -178.37(14) ?
    O141 N14 C14 C13 . . . . -6.8(2) ?
    O142 N14 C14 C13 . . . . 173.19(15) ?
    O141 N14 C14 C15 . . . . 174.98(15) ?
    O142 N14 C14 C15 . . . . -5.0(2) ?
    C13 C14 C15 C16 . . . . 0.1(2) ?
    N14 C14 C15 C16 . . . . 178.26(14) ?
    C14 C15 C16 C11 . . . . -0.3(2) ?
    N1 C11 C16 C15 . . . . 179.86(14) ?
    C12 C11 C16 C15 . . . . 0.6(2) ?
    N2 C2 C21 C22 . . . . -86.2(2) ?
    C3 C2 C21 C22 . . . . 90.25(17) ?
    C2 C3 C31 C32 . . . . -109.84(17) ?
    C2 C3 C31 C36 . . . . 70.0(2) ?
    C36 C31 C32 C33 . . . . 0.1(2) ?
    C3 C31 C32 C33 . . . . 179.95(15) ?
    C31 C32 C33 C34 . . . . -0.2(3) ?
    C32 C33 C34 C35 . . . . 0.1(3) ?
    C33 C34 C35 C36 . . . . 0.2(3) ?
    C34 C35 C36 C31 . . . . -0.2(3) ?
    C32 C31 C36 C35 . . . . 0.1(2) ?
    C3 C31 C36 C35 . . . . -179.73(15) ?
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
    N1 H1 O122 . 0.85 1.95 2.5966(17) 132
    C3 H3A O142 4_555 0.99 2.50 3.432(2) 158
    C32 H32 O142 4_555 0.95 2.52 3.349(2) 146
    C3 H3B Cg2 1_545 0.99 2.75 3.534(2) 136
