#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/46/2224671.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_2224671
loop_
_publ_author_name
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
_publ_section_title
;(E)-1-(4-Nitrophenyl)-2-(4-{[(E)-2-(4-nitrophenyl)hydrazinylidene]methyl}benzylidene)hydrazine
 dihydrate
;
_journal_coeditor_code           HG2618
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o191
_journal_page_last               o192
_journal_paper_doi               10.1107/S1600536809053963
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H16 N6 O4, 2H2 O'
_chemical_formula_moiety         'C20 H16 N6 O4, 2(H2 O)'
_chemical_formula_sum            'C20 H20 N6 O6'
_chemical_formula_weight         440.42
_chemical_name_systematic
;
(E)-1-(4-Nitrophenyl)-2-(4-{[(E)-2-(4-
nitrophenyl)hydrazinylidene]methyl}benzylidene)hydrazine dihydrate
;
_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                100.749(3)
_cell_angle_beta                 90.533(4)
_cell_angle_gamma                103.131(5)
_cell_formula_units_Z            2
_cell_length_a                   7.7549(4)
_cell_length_b                   9.3245(7)
_cell_length_c                   15.3374(11)
_cell_measurement_reflns_used    4364
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1059.56(13)
_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, 2010)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_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  0.039
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16566
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            dark-red
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.085
_refine_ls_R_factor_gt           0.060
_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)+(0.0852P)²+0.5693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.166
_refine_ls_wR_factor_ref         0.177
_reflns_number_gt                2638
_reflns_number_total             3688
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2618.cif
_cod_data_source_block           I
_cod_original_cell_volume        1059.56(12)
_cod_database_code               2224671
_cod_database_fobs_code          2224671
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 -0.2175(2) -0.6067(2) 1.41897(13) 0.0387(5) Uani d . 1 . .
O O2 -0.3174(3) -0.6708(2) 1.28198(14) 0.0421(5) Uani d . 1 . .
O O3 1.1204(2) 0.9370(2) 0.69699(13) 0.0388(5) Uani d . 1 . .
O O4 0.9881(2) 0.8999(2) 0.56744(12) 0.0340(5) Uani d . 1 . .
N N1 -0.2205(3) -0.5823(2) 1.34244(16) 0.0314(5) Uani d . 1 . .
N N2 0.2344(3) -0.0749(2) 1.26201(14) 0.0285(5) Uani d . 1 . .
H H2N 0.3112 -0.0149 1.3030 0.034 Uiso d R 1 . .
N N3 0.2300(3) -0.0459(2) 1.17772(14) 0.0279(5) Uani d . 1 . .
N N4 0.5188(3) 0.3449(2) 0.80714(13) 0.0268(5) Uani d . 1 . .
N N5 0.5234(3) 0.3707(2) 0.72248(13) 0.0272(5) Uani d . 1 . .
H H5N 0.4508 0.3089 0.6803 0.033 Uiso d R 1 . .
N N6 1.0012(3) 0.8658(2) 0.64104(14) 0.0281(5) Uani d . 1 . .
C C1 -0.1068(3) -0.4476(3) 1.32299(17) 0.0264(6) Uani d . 1 . .
C C2 0.0140(3) -0.3527(3) 1.38838(18) 0.0298(6) Uani d . 1 . .
H H2 0.0190 -0.3740 1.4464 0.036 Uiso calc R 1 . .
C C3 0.1262(3) -0.2277(3) 1.36776(17) 0.0275(6) Uani d . 1 . .
H H3 0.2084 -0.1618 1.4119 0.033 Uiso calc R 1 . .
C C4 0.1193(3) -0.1974(3) 1.28162(16) 0.0250(6) Uani d . 1 . .
C C5 -0.0061(3) -0.2935(3) 1.21764(18) 0.0312(6) Uani d . 1 . .
H H5 -0.0141 -0.2721 1.1597 0.037 Uiso calc R 1 . .
C C6 -0.1168(4) -0.4174(3) 1.23830(19) 0.0330(6) Uani d . 1 . .
H H6 -0.2005 -0.4829 1.1946 0.040 Uiso calc R 1 . .
C C7 0.3492(3) 0.0666(3) 1.16298(17) 0.0285(6) Uani d . 1 . .
H H7 0.4329 0.1230 1.2094 0.034 Uiso calc R 1 . .
C C8 0.3571(3) 0.1086(3) 1.07560(17) 0.0270(6) Uani d . 1 . .
C C9 0.4848(4) 0.2336(3) 1.06298(18) 0.0371(7) Uani d . 1 . .
H H9 0.5628 0.2913 1.1114 0.044 Uiso calc R 1 . .
C C10 0.4993(4) 0.2748(3) 0.98095(18) 0.0365(7) Uani d . 1 . .
H H10 0.5857 0.3617 0.9740 0.044 Uiso calc R 1 . .
C C11 0.3902(3) 0.1917(3) 0.90894(17) 0.0267(6) Uani d . 1 . .
C C12 0.2590(4) 0.0692(3) 0.92239(19) 0.0399(7) Uani d . 1 . .
H H12 0.1792 0.0129 0.8743 0.048 Uiso calc R 1 . .
C C13 0.2436(4) 0.0288(3) 1.00415(19) 0.0400(7) Uani d . 1 . .
H H13 0.1535 -0.0554 1.0117 0.048 Uiso calc R 1 . .
C C14 0.4076(3) 0.2275(3) 0.82018(17) 0.0274(6) Uani d . 1 . .
H H14 0.3356 0.1628 0.7716 0.033 Uiso calc R 1 . .
C C15 0.6399(3) 0.4935(3) 0.70347(16) 0.0246(6) Uani d . 1 . .
C C16 0.7616(3) 0.5904(3) 0.76914(16) 0.0259(6) Uani d . 1 . .
H H16 0.7625 0.5721 0.8280 0.031 Uiso calc R 1 . .
C C17 0.8788(3) 0.7112(3) 0.74798(17) 0.0267(6) Uani d . 1 . .
H H17 0.9626 0.7757 0.7920 0.032 Uiso calc R 1 . .
C C18 0.8752(3) 0.7394(3) 0.66236(17) 0.0251(6) Uani d . 1 . .
C C19 0.7543(3) 0.6461(3) 0.59689(17) 0.0275(6) Uani d . 1 . .
H H19 0.7515 0.6670 0.5387 0.033 Uiso calc R 1 . .
C C20 0.6385(3) 0.5231(3) 0.61741(17) 0.0274(6) Uani d . 1 . .
H H20 0.5569 0.4577 0.5727 0.033 Uiso calc R 1 . .
O O1W 0.3412(2) 0.1327(2) 0.56735(12) 0.0346(5) Uani d D 1 . .
H H1W 0.2326(16) 0.095(3) 0.565(2) 0.052 Uiso d D 1 . .
H H2W 0.386(4) 0.141(4) 0.5191(12) 0.052 Uiso d D 1 . .
O O2W 0.4975(2) 0.9015(2) 0.59601(13) 0.0349(5) Uani d D 1 . .
H H3W 0.434(3) 0.961(3) 0.590(2) 0.052 Uiso d D 1 . .
H H4W 0.429(3) 0.826(2) 0.609(2) 0.052 Uiso d D 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 . . 121.7(2) ?
O2 N1 C1 . . 119.1(2) ?
O1 N1 C1 . . 119.3(2) ?
C4 N2 N3 . . 119.5(2) ?
C4 N2 H2N . . 120.4 ?
N3 N2 H2N . . 120.1 ?
C7 N3 N2 . . 115.9(2) ?
C14 N4 N5 . . 116.7(2) ?
N4 N5 C15 . . 119.9(2) ?
N4 N5 H5N . . 119.9 ?
C15 N5 H5N . . 120.2 ?
O3 N6 O4 . . 121.8(2) ?
O3 N6 C18 . . 118.8(2) ?
O4 N6 C18 . . 119.5(2) ?
C6 C1 C2 . . 121.1(2) ?
C6 C1 N1 . . 119.0(2) ?
C2 C1 N1 . . 119.9(2) ?
C3 C2 C1 . . 119.2(2) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C2 C3 C4 . . 120.2(2) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
N2 C4 C3 . . 119.3(2) ?
N2 C4 C5 . . 121.4(2) ?
C3 C4 C5 . . 119.3(2) ?
C6 C5 C4 . . 120.3(2) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C1 . . 119.9(3) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
N3 C7 C8 . . 120.8(2) ?
N3 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C13 C8 C9 . . 118.1(2) ?
C13 C8 C7 . . 122.8(2) ?
C9 C8 C7 . . 119.1(2) ?
C10 C9 C8 . . 120.9(3) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C9 C10 C11 . . 120.9(2) ?
C9 C10 H10 . . 119.5 ?
C11 C10 H10 . . 119.5 ?
C10 C11 C12 . . 118.1(2) ?
C10 C11 C14 . . 122.4(2) ?
C12 C11 C14 . . 119.5(2) ?
C13 C12 C11 . . 121.0(3) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C12 C13 C8 . . 121.0(2) ?
C12 C13 H13 . . 119.5 ?
C8 C13 H13 . . 119.5 ?
N4 C14 C11 . . 120.8(2) ?
N4 C14 H14 . . 119.6 ?
C11 C14 H14 . . 119.6 ?
N5 C15 C20 . . 119.6(2) ?
N5 C15 C16 . . 121.0(2) ?
C20 C15 C16 . . 119.4(2) ?
C17 C16 C15 . . 119.8(2) ?
C17 C16 H16 . . 120.1 ?
C15 C16 H16 . . 120.1 ?
C16 C17 C18 . . 120.1(2) ?
C16 C17 H17 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C17 C18 C19 . . 120.9(2) ?
C17 C18 N6 . . 119.3(2) ?
C19 C18 N6 . . 119.8(2) ?
C20 C19 C18 . . 119.2(2) ?
C20 C19 H19 . . 120.4 ?
C18 C19 H19 . . 120.4 ?
C19 C20 C15 . . 120.6(2) ?
C19 C20 H20 . . 119.7 ?
C15 C20 H20 . . 119.7 ?
H1W O1W H2W . . 117(3) ?
H3W O2W H4W . . 106(3) ?
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 . 1.238(3) ?
O2 N1 . 1.235(3) ?
O3 N6 . 1.235(3) ?
O4 N6 . 1.237(3) ?
N1 C1 . 1.444(3) ?
N2 C4 . 1.364(3) ?
N2 N3 . 1.371(3) ?
N2 H2N . 0.8796 ?
N3 C7 . 1.288(3) ?
N4 C14 . 1.280(3) ?
N4 N5 . 1.364(3) ?
N5 C15 . 1.368(3) ?
N5 H5N . 0.8799 ?
N6 C18 . 1.442(3) ?
C1 C6 . 1.384(4) ?
C1 C2 . 1.393(4) ?
C2 C3 . 1.377(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.405(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.404(4) ?
C5 C6 . 1.365(4) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.463(3) ?
C7 H7 . 0.9500 ?
C8 C13 . 1.382(4) ?
C8 C9 . 1.393(4) ?
C9 C10 . 1.381(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.379(4) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.395(4) ?
C11 C14 . 1.461(3) ?
C12 C13 . 1.374(4) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C20 . 1.398(3) ?
C15 C16 . 1.406(4) ?
C16 C17 . 1.370(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.388(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.389(4) ?
C19 C20 . 1.376(3) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
O1W H1W . 0.833(10) ?
O1W H2W . 0.831(10) ?
O2W H3W . 0.839(10) ?
O2W H4W . 0.836(10) ?
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
O1W H1w O4 1_445 0.833(17) 2.32(2) 3.084(2) 153(2)
O1W H2w O2w 2_666 0.83(2) 2.01(2) 2.808(3) 163(3)
N5 H5n O1w 1_555 0.88 2.17 3.021(3) 163
O2W H3w O1w 1_565 0.84(3) 1.98(3) 2.800(3) 165(3)
O2W H4w O1 2_557 0.84(2) 2.28(2) 3.061(3) 156(3)
O2W H4w O2 2_557 0.84(2) 2.45(2) 3.204(3) 150(3)
N2 H2n O2w 2_667 0.88 2.09 2.959(3) 172
C7 H7 O2 1_665 0.95 2.48 3.374(3) 157
C14 H14 O3 1_445 0.95 2.45 3.338(3) 156
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
C4 N2 N3 C7 . . . . -176.2(2) ?
C14 N4 N5 C15 . . . . -179.5(2) ?
O2 N1 C1 C6 . . . . 3.6(3) ?
O1 N1 C1 C6 . . . . -177.0(2) ?
O2 N1 C1 C2 . . . . -174.6(2) ?
O1 N1 C1 C2 . . . . 4.8(3) ?
C6 C1 C2 C3 . . . . -0.6(4) ?
N1 C1 C2 C3 . . . . 177.6(2) ?
C1 C2 C3 C4 . . . . -0.5(4) ?
N3 N2 C4 C3 . . . . 179.1(2) ?
N3 N2 C4 C5 . . . . -1.1(3) ?
C2 C3 C4 N2 . . . . -178.5(2) ?
C2 C3 C4 C5 . . . . 1.7(4) ?
N2 C4 C5 C6 . . . . 178.3(2) ?
C3 C4 C5 C6 . . . . -1.9(4) ?
C4 C5 C6 C1 . . . . 0.8(4) ?
C2 C1 C6 C5 . . . . 0.5(4) ?
N1 C1 C6 C5 . . . . -177.7(2) ?
N2 N3 C7 C8 . . . . -179.8(2) ?
N3 C7 C8 C13 . . . . -2.3(4) ?
N3 C7 C8 C9 . . . . 178.2(2) ?
C13 C8 C9 C10 . . . . -1.1(4) ?
C7 C8 C9 C10 . . . . 178.4(2) ?
C8 C9 C10 C11 . . . . -1.3(4) ?
C9 C10 C11 C12 . . . . 3.1(4) ?
C9 C10 C11 C14 . . . . -176.8(2) ?
C10 C11 C12 C13 . . . . -2.6(4) ?
C14 C11 C12 C13 . . . . 177.3(3) ?
C11 C12 C13 C8 . . . . 0.3(5) ?
C9 C8 C13 C12 . . . . 1.6(4) ?
C7 C8 C13 C12 . . . . -177.9(3) ?
N5 N4 C14 C11 . . . . -178.8(2) ?
C10 C11 C14 N4 . . . . -4.7(4) ?
C12 C11 C14 N4 . . . . 175.3(2) ?
N4 N5 C15 C20 . . . . -177.1(2) ?
N4 N5 C15 C16 . . . . 3.0(3) ?
N5 C15 C16 C17 . . . . 178.9(2) ?
C20 C15 C16 C17 . . . . -0.9(4) ?
C15 C16 C17 C18 . . . . 1.2(4) ?
C16 C17 C18 C19 . . . . -0.3(4) ?
C16 C17 C18 N6 . . . . -179.1(2) ?
O3 N6 C18 C17 . . . . 7.1(3) ?
O4 N6 C18 C17 . . . . -173.2(2) ?
O3 N6 C18 C19 . . . . -171.7(2) ?
O4 N6 C18 C19 . . . . 7.9(3) ?
C17 C18 C19 C20 . . . . -0.9(4) ?
N6 C18 C19 C20 . . . . 177.9(2) ?
C18 C19 C20 C15 . . . . 1.2(4) ?
N5 C15 C20 C19 . . . . 179.9(2) ?
C16 C15 C20 C19 . . . . -0.3(4) ?
