#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/12/2231274.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_2231274
loop_
_publ_author_name
'Li, Hongbo'
'Ni, Xiaocheng'
_publ_section_title
;
 2-Cyano-N'-(5-hydroxy-2-nitrobenzylidene)acetohydrazide
 monohydrate
;
_journal_coeditor_code           QM2014
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2002
_journal_paper_doi               10.1107/S1600536811025463
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H8 N4 O4, H2 O'
_chemical_formula_moiety         'C10 H8 N4 O4, H2 O'
_chemical_formula_sum            'C10 H10 N4 O5'
_chemical_formula_weight         266.22
_chemical_name_systematic
;
2-Cyano-N'-(5-hydroxy-2-nitrobenzylidene)acetohydrazide monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.312(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6630(10)
_cell_length_b                   13.238(2)
_cell_length_c                   19.305(2)
_cell_measurement_reflns_used    2122
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.6
_cell_measurement_theta_min      2.6
_cell_volume                     1191.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8851
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_correction_T_min  0.9679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0727P)²+0.3422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1478
_reflns_number_gt                1935
_reflns_number_total             2531
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2014.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2231274
_cod_database_fobs_code          2231274
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'
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
N N1 0.1870(4) 0.73554(14) -0.16790(9) 0.0507(5) Uani d . 1 1
N N2 0.5017(3) 0.64853(11) 0.03310(8) 0.0366(4) Uani d . 1 1
N N3 0.7235(3) 0.57994(11) 0.03500(8) 0.0369(4) Uani d D 1 1
N N4 0.9875(6) 0.5194(2) 0.26634(12) 0.0898(8) Uani d . 1 1
O O1 0.3932(4) 0.67914(16) -0.16953(9) 0.0813(6) Uani d . 1 1
O O2 0.0556(5) 0.75595(16) -0.22076(9) 0.0877(7) Uani d . 1 1
O O3 1.0378(3) 0.48653(11) 0.09451(7) 0.0476(4) Uani d . 1 1
O O4 -0.2421(3) 0.91461(12) 0.07021(8) 0.0574(4) Uani d D 1 1
O O5 0.0680(5) 0.8597(2) 0.18259(10) 0.0919(7) Uani d D 1 1
C C1 0.2056(4) 0.75195(13) -0.03818(9) 0.0350(4) Uani d . 1 1
C C2 0.0916(4) 0.77958(14) -0.10307(10) 0.0403(5) Uani d . 1 1
C C3 -0.1218(5) 0.85279(15) -0.10828(12) 0.0481(5) Uani d . 1 1
H H3 -0.1921 0.8711 -0.1517 0.058 Uiso calc R 1 1
C C4 -0.2291(5) 0.89799(15) -0.05048(12) 0.0489(5) Uani d . 1 1
H H4A -0.3714 0.9469 -0.0545 0.059 Uiso calc R 1 1
C C5 -0.1244(4) 0.87064(14) 0.01452(11) 0.0424(5) Uani d . 1 1
C C6 0.0926(4) 0.79932(13) 0.01966(10) 0.0378(4) Uani d . 1 1
H H6 0.1646 0.7828 0.0632 0.045 Uiso calc R 1 1
C C7 0.4343(4) 0.67707(13) -0.02755(9) 0.0362(4) Uani d . 1 1
H H7 0.5302 0.6505 -0.0655 0.043 Uiso calc R 1 1
C C8 0.8365(4) 0.54622(14) 0.09432(10) 0.0379(4) Uani d . 1 1
C C9 0.7002(5) 0.58300(19) 0.16020(10) 0.0589(6) Uani d . 1 1
H H9A 0.6945 0.6562 0.1602 0.071 Uiso calc R 1 1
H H9B 0.5047 0.5583 0.1628 0.071 Uiso calc R 1 1
C C10 0.8611(6) 0.54791(19) 0.21982(12) 0.0608(6) Uani d . 1 1
H H3A 0.804(5) 0.5585(18) -0.0045(8) 0.073 Uiso d D 1 1
H H4 -0.158(6) 0.891(2) 0.1062(10) 0.091 Uiso d D 1 1
H H5A -0.017(5) 0.839(2) 0.2181(10) 0.091 Uiso d D 1 1
H H5B 0.220(4) 0.889(2) 0.1943(14) 0.091 Uiso d 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 0.0033 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
O2 N1 O1 120.5(2)
O2 N1 C2 118.5(2)
O1 N1 C2 120.92(17)
C7 N2 N3 113.79(15)
C8 N3 N2 122.43(15)
C8 N3 H3A 117.2(17)
N2 N3 H3A 120.3(17)
C5 O4 H4 108(2)
H5A O5 H5B 110(2)
C6 C1 C2 117.14(17)
C6 C1 C7 118.09(16)
C2 C1 C7 124.77(17)
C3 C2 C1 120.78(19)
C3 C2 N1 116.07(18)
C1 C2 N1 123.15(18)
C4 C3 C2 120.77(19)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 119.69(19)
C3 C4 H4A 120.2
C5 C4 H4A 120.2
O4 C5 C6 122.62(18)
O4 C5 C4 117.80(18)
C6 C5 C4 119.59(19)
C1 C6 C5 122.01(18)
C1 C6 H6 119.0
C5 C6 H6 119.0
N2 C7 C1 120.39(17)
N2 C7 H7 119.8
C1 C7 H7 119.8
O3 C8 N3 121.08(17)
O3 C8 C9 122.14(17)
N3 C8 C9 116.76(17)
C10 C9 C8 110.41(19)
C10 C9 H9A 109.6
C8 C9 H9A 109.6
C10 C9 H9B 109.6
C8 C9 H9B 109.6
H9A C9 H9B 108.1
N4 C10 C9 179.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O2 1.218(2)
N1 O1 1.218(2)
N1 C2 1.453(3)
N2 C7 1.268(2)
N2 N3 1.377(2)
N3 C8 1.335(2)
N3 H3A 0.898(10)
N4 C10 1.136(3)
O3 C8 1.227(2)
O4 C5 1.343(3)
O4 H4 0.856(10)
O5 H5A 0.840(10)
O5 H5B 0.839(10)
C1 C6 1.387(3)
C1 C2 1.407(3)
C1 C7 1.470(2)
C2 C3 1.392(3)
C3 C4 1.363(3)
C3 H3 0.9300
C4 C5 1.392(3)
C4 H4A 0.9300
C5 C6 1.387(3)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.506(3)
C9 C10 1.447(3)
C9 H9A 0.9700
C9 H9B 0.9700
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
O5 H5B N4 2_655 0.839(10) 2.323(16) 3.117(4) 158(3)
O5 H5A O1 4_576 0.840(10) 2.224(15) 3.017(3) 157(3)
O4 H4 O5 . 0.856(10) 1.854(12) 2.700(3) 170(3)
N3 H3A O3 3_765 0.898(10) 1.983(10) 2.880(2) 177(2)
