##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-[(E)-Anthracen-9-ylmethylidene]-2-(2,4-dinitrophenyl)hydrazine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H14 N4 O4'
_chemical_formula_sum     'C21 H14 N4 O4'
_chemical_formula_iupac     'C21 H14 N4 O4'
_chemical_formula_weight     386.36
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     5.6355(4)
_cell_length_b     8.1597(5)
_cell_length_c     36.794(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1691.95(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1164
_cell_measurement_theta_min     2.9985
_cell_measurement_theta_max     18.7647
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.08
_exptl_crystal_size_mid     0.02
_exptl_crystal_size_min     0.01
_exptl_crystal_density_diffrn     1.517
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     146
_exptl_absorpt_coefficient_mu     0.108
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2000)'
_exptl_absorpt_correction_T_min     0.764
_exptl_absorpt_correction_T_max     0.999
_exptl_special_details     ?
_diffrn_ambient_temperature     293(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 APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18174
_diffrn_reflns_av_R_equivalents     0.1323
_diffrn_reflns_av_sigmaI/netI     0.1964
_diffrn_reflns_theta_min     3.34
_diffrn_reflns_theta_max     27.34
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -46
_diffrn_reflns_limit_l_max     46
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     ?
_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     3708
_reflns_number_gt     1466
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.2255
_refine_ls_R_factor_gt     0.0738
_refine_ls_wR_factor_gt     0.1633
_refine_ls_wR_factor_ref     0.2422
_refine_ls_goodness_of_fit_ref     0.879
_refine_ls_restrained_S_all     0.879
_refine_ls_number_reflns     3708
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.1212P)²] 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     0.253
_refine_diff_density_min     -0.217
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.036(5)
_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, 2003)'
_computing_cell_refinement     'SAINT (Bruker, 2003)'
_computing_data_reduction     'SAINT (Bruker, 2003)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg, 2006)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 2012)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.2253(10) 0.1891(7) 0.26020(13) 0.0951(18) Uani d . 1 1 . .
    O O2 -0.0875(10) 0.1412(7) 0.22882(14) 0.0932(17) Uani d . 1 1 . .
    O O3 -0.1033(8) 0.2666(5) 0.10426(11) 0.0669(13) Uani d . 1 1 . .
    O O4 0.1605(8) 0.4177(5) 0.07843(12) 0.0703(13) Uani d . 1 1 . .
    N N1 0.1114(12) 0.2008(7) 0.23234(16) 0.0725(16) Uani d . 1 1 . .
    N N2 0.0789(10) 0.3493(6) 0.10576(14) 0.0558(14) Uani d . 1 1 . .
    N N3 0.5138(9) 0.5396(6) 0.11586(14) 0.0559(14) Uani d . 1 1 . .
    H H03 0.4470 0.5385 0.0948 0.067 Uiso calc R 1 1 . .
    N N4 0.7204(9) 0.6275(6) 0.12078(13) 0.0561(14) Uani d . 1 1 . .
    C C1 0.4148(10) 0.4550(7) 0.14367(16) 0.0475(14) Uani d . 1 1 . .
    C C2 0.2018(10) 0.3647(7) 0.13979(15) 0.0481(15) Uani d . 1 1 . .
    C C3 0.1020(12) 0.2848(7) 0.16947(17) 0.0554(16) Uani d . 1 1 . .
    H H3 -0.0398 0.2275 0.1671 0.066 Uiso calc R 1 1 . .
    C C4 0.2148(11) 0.2921(8) 0.20181(16) 0.0536(16) Uani d . 1 1 . .
    C C5 0.4246(11) 0.3756(8) 0.20701(17) 0.0582(17) Uani d . 1 1 . .
    H H5 0.4983 0.3771 0.2296 0.070 Uiso calc R 1 1 . .
    C C6 0.5215(11) 0.4563(8) 0.17795(17) 0.0562(16) Uani d . 1 1 . .
    H H6 0.6626 0.5137 0.1811 0.067 Uiso calc R 1 1 . .
    C C7 0.7784(10) 0.7172(7) 0.09321(16) 0.0497(15) Uani d . 1 1 . .
    H H7 0.6795 0.7136 0.0730 0.060 Uiso calc R 1 1 . .
    C C8 0.9857(10) 0.8234(7) 0.09117(16) 0.0490(15) Uani d . 1 1 . .
    C C9 1.0328(10) 0.8946(7) 0.05641(16) 0.0482(15) Uani d . 1 1 . .
    C C10 0.8823(13) 0.8738(8) 0.02552(16) 0.0609(17) Uani d . 1 1 . .
    H H10 0.7477 0.8083 0.0274 0.073 Uiso calc R 1 1 . .
    C C11 0.9330(12) 0.9482(8) -0.00647(18) 0.0667(19) Uani d . 1 1 . .
    H H11 0.8285 0.9355 -0.0258 0.080 Uiso calc R 1 1 . .
    C C12 1.1380(13) 1.0440(8) -0.0115(2) 0.070(2) Uani d . 1 1 . .
    H H12 1.1724 1.0905 -0.0339 0.084 Uiso calc R 1 1 . .
    C C13 1.2834(13) 1.0664(7) 0.01730(19) 0.0652(18) Uani d . 1 1 . .
    H H13 1.4182 1.1309 0.0145 0.078 Uiso calc R 1 1 . .
    C C14 1.2364(12) 0.9944(7) 0.05161(17) 0.0519(15) Uani d . 1 1 . .
    C C15 1.3859(11) 1.0226(7) 0.08107(18) 0.0583(17) Uani d . 1 1 . .
    H H15 1.5209 1.0862 0.0777 0.070 Uiso calc R 1 1 . .
    C C21 1.1340(10) 0.8580(7) 0.12098(15) 0.0466(14) Uani d . 1 1 . .
    C C16 1.3403(10) 0.9587(7) 0.11560(17) 0.0525(16) Uani d . 1 1 . .
    C C17 1.4973(12) 0.9911(8) 0.14472(18) 0.0591(17) Uani d . 1 1 . .
    H H17 1.6304 1.0560 0.1407 0.071 Uiso calc R 1 1 . .
    C C18 1.4578(12) 0.9301(8) 0.1779(2) 0.0660(19) Uani d . 1 1 . .
    H H18 1.5653 0.9491 0.1966 0.079 Uiso calc R 1 1 . .
    C C19 1.2511(12) 0.8366(8) 0.18424(18) 0.0635(18) Uani d . 1 1 . .
    H H19 1.2202 0.7970 0.2075 0.076 Uiso calc R 1 1 . .
    C C20 1.0978(12) 0.8040(8) 0.15704(17) 0.0604(17) Uani d . 1 1 . .
    H H20 0.9623 0.7433 0.1622 0.073 Uiso calc R 1 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
    O1 N1 . 1.214(7) ?
    O2 N1 . 1.229(7) ?
    O3 N2 . 1.230(6) ?
    O4 N2 . 1.238(6) ?
    N1 C4 . 1.469(8) ?
    N2 C2 . 1.436(7) ?
    N3 C1 . 1.355(7) ?
    N3 N4 . 1.379(6) ?
    N3 H03 . 0.8600 ?
    N4 C7 . 1.293(7) ?
    C1 C6 . 1.397(8) ?
    C1 C2 . 1.416(8) ?
    C2 C3 . 1.390(8) ?
    C3 C4 . 1.350(8) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.378(8) ?
    C5 C6 . 1.369(8) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.456(7) ?
    C7 H7 . 0.9300 ?
    C8 C21 . 1.408(8) ?
    C8 C9 . 1.430(8) ?
    C9 C14 . 1.418(8) ?
    C9 C10 . 1.428(8) ?
    C10 C11 . 1.355(8) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.407(9) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.351(9) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.418(8) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.392(8) ?
    C15 C16 . 1.397(8) ?
    C15 H15 . 0.9300 ?
    C21 C20 . 1.413(7) ?
    C21 C16 . 1.437(8) ?
    C16 C17 . 1.414(8) ?
    C17 C18 . 1.337(9) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.412(9) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.348(8) ?
    C19 H19 . 0.9300 ?
    C20 H20 . 0.9300 ?
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
    O1 N1 O2 . . 122.7(6) ?
    O1 N1 C4 . . 118.4(6) ?
    O2 N1 C4 . . 118.8(6) ?
    O3 N2 O4 . . 121.4(5) ?
    O3 N2 C2 . . 119.3(5) ?
    O4 N2 C2 . . 119.3(5) ?
    C1 N3 N4 . . 120.9(5) ?
    C1 N3 H03 . . 119.6 ?
    N4 N3 H03 . . 119.6 ?
    C7 N4 N3 . . 113.9(5) ?
    N3 C1 C6 . . 120.0(6) ?
    N3 C1 C2 . . 122.6(6) ?
    C6 C1 C2 . . 117.4(5) ?
    C3 C2 C1 . . 120.5(5) ?
    C3 C2 N2 . . 116.7(5) ?
    C1 C2 N2 . . 122.8(5) ?
    C4 C3 C2 . . 118.8(6) ?
    C4 C3 H3 . . 120.6 ?
    C2 C3 H3 . . 120.6 ?
    C3 C4 C5 . . 123.2(6) ?
    C3 C4 N1 . . 117.7(6) ?
    C5 C4 N1 . . 119.0(6) ?
    C6 C5 C4 . . 118.1(6) ?
    C6 C5 H5 . . 120.9 ?
    C4 C5 H5 . . 120.9 ?
    C5 C6 C1 . . 122.0(6) ?
    C5 C6 H6 . . 119.0 ?
    C1 C6 H6 . . 119.0 ?
    N4 C7 C8 . . 125.5(6) ?
    N4 C7 H7 . . 117.3 ?
    C8 C7 H7 . . 117.3 ?
    C21 C8 C9 . . 120.4(5) ?
    C21 C8 C7 . . 123.7(5) ?
    C9 C8 C7 . . 115.9(5) ?
    C14 C9 C10 . . 116.7(5) ?
    C14 C9 C8 . . 119.7(5) ?
    C10 C9 C8 . . 123.6(6) ?
    C11 C10 C9 . . 120.8(7) ?
    C11 C10 H10 . . 119.6 ?
    C9 C10 H10 . . 119.6 ?
    C10 C11 C12 . . 122.4(7) ?
    C10 C11 H11 . . 118.8 ?
    C12 C11 H11 . . 118.8 ?
    C13 C12 C11 . . 118.1(6) ?
    C13 C12 H12 . . 121.0 ?
    C11 C12 H12 . . 121.0 ?
    C12 C13 C14 . . 121.9(7) ?
    C12 C13 H13 . . 119.0 ?
    C14 C13 H13 . . 119.0 ?
    C15 C14 C13 . . 120.8(6) ?
    C15 C14 C9 . . 119.2(6) ?
    C13 C14 C9 . . 120.0(6) ?
    C14 C15 C16 . . 122.4(6) ?
    C14 C15 H15 . . 118.8 ?
    C16 C15 H15 . . 118.8 ?
    C8 C21 C20 . . 125.7(6) ?
    C8 C21 C16 . . 119.2(5) ?
    C20 C21 C16 . . 115.1(6) ?
    C15 C16 C17 . . 120.3(6) ?
    C15 C16 C21 . . 119.2(6) ?
    C17 C16 C21 . . 120.6(6) ?
    C18 C17 C16 . . 121.2(6) ?
    C18 C17 H17 . . 119.4 ?
    C16 C17 H17 . . 119.4 ?
    C17 C18 C19 . . 119.3(6) ?
    C17 C18 H18 . . 120.4 ?
    C19 C18 H18 . . 120.4 ?
    C20 C19 C18 . . 120.8(6) ?
    C20 C19 H19 . . 119.6 ?
    C18 C19 H19 . . 119.6 ?
    C19 C20 C21 . . 122.9(6) ?
    C19 C20 H20 . . 118.6 ?
    C21 C20 H20 . . 118.6 ?
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
    N3 H03 O4 . 0.86 1.99 2.617(7) 129.4
    C11 H11 O4 3_565 0.93 2.47 3.251(8) 142.2
    C20 H20 N4 . 0.93 2.25 2.894(8) 125.5
data_global
_journal_date_recd_electronic     2013-02-15
_journal_date_accepted     2013-04-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      5
_journal_page_first     o705
_journal_page_last     o705
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813009197
_journal_coeditor_code     BT6891
_publ_contact_author_name     'Consuelo Yuste-Vivas'
_publ_contact_author_address
;
     Faculdade Ciências e Tecnologia
     Departamento de Física
     Universidade de Coimbra
     P-3004-516 Coimbra
     Portugal
;
_publ_contact_author_email     xelo@teor.fis.uc.pt
_publ_contact_author_fax     351-239-829158
_publ_contact_author_phone     351-239-410648
_publ_section_title
;
1-[(E)-Anthracen-9-ylmethylidene]-2-(2,4-dinitrophenyl)hydrazine
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'A. e Silva, Joana de' .
;
Chemistry Department
University of Coimbra
P-3004-530 Coimbra
Portugal
;
    'Yuste-Vivas, Consuelo'
;
;
;
CEMDRX
Physics Department
University of Coimbra
P-3004-516 Coimbra
Portugal
;
    'Sobral, Abilio J. F. N.' .
;
Chemistry Department
University of Coimbra
P-3004-530 Coimbra
Portugal
;
    ' Silva, Manuela Ramos' .
;
CEMDRX
Physics Department
University of Coimbra
P-3004-516 Coimbra
Portugal
;
_publ_section_synopsis     .
