#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/84/2238414.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_2238414
loop_
_publ_author_name
'Essid, Manel'
'Marouani, Houda'
'Al-Deyab, Salem S.'
'Rzaigui, Mohamed'
_publ_section_title
;
 N'-(2,4-Dinitrophenyl)acetohydrazide monohydrate
;
_journal_coeditor_code           PV2637
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1249
_journal_paper_doi               10.1107/S1600536813018916
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C8 H8 N4 O5 , H2 O'
_chemical_formula_moiety         'C8 H8 N4 O5, H2 O'
_chemical_formula_sum            'C8 H10 N4 O6'
_chemical_formula_weight         258.20
_chemical_name_systematic
;
N'-(2,4-Dinitrophenyl)acetohydrazide monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.044(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.702(2)
_cell_length_b                   7.057(3)
_cell_length_c                   21.550(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      11
_cell_measurement_theta_min      9
_cell_volume                     1107.2(6)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;ORTEP-3 for Windows (Farrugia, 2012)
and DIAMOND (Brandenburg & Putz, 2005)
;
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.1391
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7469
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.233
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         5411
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.2385
_refine_ls_R_factor_gt           0.0712
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0627P)²+0.2081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1947
_reflns_number_gt                2771
_reflns_number_total             5411
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2637.cif
_cod_data_source_block           I
_cod_original_cell_volume        1107.3(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238414
_cod_database_fobs_code          2238414
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 OW 0.8341(3) 0.6774(3) 0.23696(8) 0.0526(5) Uani d D 1 1
H H1W 0.784(4) 0.583(3) 0.2497(13) 0.088(11) Uiso d D 1 1
H H2W 0.827(4) 0.672(5) 0.1972(6) 0.091(11) Uiso d D 1 1
H H2N 0.894(4) 0.171(4) 0.1927(14) 0.073(9) Uiso d . 1 1
H H1N 0.762(3) -0.050(4) 0.2501(11) 0.052(7) Uiso d . 1 1
C C1 0.6447(3) 0.1614(3) 0.12985(10) 0.0332(4) Uani d . 1 1
N N2 0.7775(3) 0.1390(3) 0.18850(8) 0.0416(5) Uani d . 1 1
C C2 0.6778(3) 0.2383(3) 0.07398(10) 0.0347(5) Uani d . 1 1
C C4 0.3649(3) 0.2020(3) 0.00937(10) 0.0387(5) Uani d . 1 1
N N3 0.8583(3) 0.2980(3) 0.07563(10) 0.0467(5) Uani d . 1 1
N N4 0.2219(3) 0.2185(3) -0.05403(10) 0.0496(5) Uani d . 1 1
C C3 0.5376(3) 0.2593(3) 0.01484(10) 0.0383(5) Uani d . 1 1
H H3 0.5615 0.3125 -0.0210 0.046 Uiso calc R 1 1
N N1 0.7353(3) 0.0698(3) 0.24205(9) 0.0410(5) Uani d . 1 1
C C6 0.4620(3) 0.1034(3) 0.12134(10) 0.0385(5) Uani d . 1 1
H H6 0.4349 0.0515 0.1568 0.046 Uiso calc R 1 1
C C5 0.3250(3) 0.1218(3) 0.06262(11) 0.0422(5) Uani d . 1 1
H H5 0.2065 0.0815 0.0580 0.051 Uiso calc R 1 1
O O5 0.6823(3) 0.3600(3) 0.27355(9) 0.0607(5) Uani d . 1 1
C C7 0.6972(3) 0.1892(3) 0.28405(10) 0.0388(5) Uani d . 1 1
O O4 0.2556(3) 0.3098(3) -0.09698(8) 0.0683(6) Uani d . 1 1
O O2 0.8788(3) 0.3578(3) 0.02501(9) 0.0723(6) Uani d . 1 1
O O1 0.9859(2) 0.2867(3) 0.12714(9) 0.0685(6) Uani d . 1 1
C C8 0.6708(3) 0.1000(4) 0.34342(10) 0.0492(6) Uani d . 1 1
H H8A 0.7672 0.1403 0.3820 0.074 Uiso calc R 1 1
H H8B 0.6741 -0.0355 0.3397 0.074 Uiso calc R 1 1
H H8C 0.5542 0.1378 0.3465 0.074 Uiso calc R 1 1
O O3 0.0748(3) 0.1398(3) -0.06187(10) 0.0722(6) Uani 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 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 4 2
-1 2 10
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1W OW H2W 114(2)
N2 C1 C2 123.22(18)
N2 C1 C6 120.24(18)
C2 C1 C6 116.53(18)
C1 N2 N1 120.55(18)
C1 N2 H2N 119.4(18)
N1 N2 H2N 120.0(18)
C3 C2 C1 121.36(18)
C3 C2 N3 116.61(18)
C1 C2 N3 122.03(18)
C3 C4 C5 121.3(2)
C3 C4 N4 118.6(2)
C5 C4 N4 120.1(2)
O1 N3 O2 122.08(19)
O1 N3 C2 119.13(17)
O2 N3 C2 118.79(19)
O3 N4 O4 123.4(2)
O3 N4 C4 118.5(2)
O4 N4 C4 118.1(2)
C4 C3 C2 119.74(19)
C4 C3 H3 120.1
C2 C3 H3 120.1
C7 N1 N2 120.3(2)
C7 N1 H1N 124.5(16)
N2 N1 H1N 113.5(16)
C5 C6 C1 121.78(19)
C5 C6 H6 119.1
C1 C6 H6 119.1
C6 C5 C4 119.25(19)
C6 C5 H5 120.4
C4 C5 H5 120.4
O5 C7 N1 121.5(2)
O5 C7 C8 122.7(2)
N1 C7 C8 115.7(2)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
OW H1W 0.856(10)
OW H2W 0.841(9)
C1 N2 1.351(3)
C1 C2 1.418(3)
C1 C6 1.419(3)
N2 N1 1.386(2)
N2 H2N 0.90(3)
C2 C3 1.384(3)
C2 N3 1.442(3)
C4 C3 1.358(3)
C4 C5 1.400(3)
C4 N4 1.453(3)
N3 O1 1.222(2)
N3 O2 1.227(2)
N4 O3 1.223(3)
N4 O4 1.224(3)
C3 H3 0.9300
N1 C7 1.338(3)
N1 H1N 0.88(3)
C6 C5 1.364(3)
C6 H6 0.9300
C5 H5 0.9300
O5 C7 1.225(3)
C7 C8 1.498(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
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
OW H1W O5 . 0.856(10) 1.905(11) 2.759(3) 175(3)
OW H2W O4 3_665 0.841(9) 2.047(13) 2.868(3) 165(3)
N1 H1N OW 1_545 0.88(3) 2.04(3) 2.883(3) 160(2)
N2 H2N O1 . 0.90(3) 1.96(3) 2.607(2) 128(2)
N2 H2N OW 2_745 0.90(3) 2.15(3) 2.910(3) 142(2)
C6 H6 O5 2_645 0.93 2.40 3.310(3) 164.8
