#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/05/2230595.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_2230595
loop_
_publ_author_name
'Liu, Shi-Yong'
'Wang, Xiao-Ling'
_publ_section_title
;
 (E)-N'-(2-Chloro-5-nitrobenzylidene)-3-methoxybenzohydrazide
 monohydrate
;
_journal_coeditor_code           CV5103
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1625
_journal_paper_doi               10.1107/S1600536811020769
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H12 Cl N3 O4 , H2 O'
_chemical_formula_moiety         'C15 H12 Cl N3 O4, H2 O'
_chemical_formula_sum            'C15 H14 Cl N3 O5'
_chemical_formula_weight         351.74
_chemical_name_systematic
;
(E)-N'-(2-Chloro-5-nitrobenzylidene)-3-methoxybenzohydrazide
monohydrate
;
_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           SHELXL97
_cell_angle_alpha                83.820(18)
_cell_angle_beta                 89.953(18)
_cell_angle_gamma                80.190(18)
_cell_formula_units_Z            2
_cell_length_a                   7.176(2)
_cell_length_b                   7.179(2)
_cell_length_c                   15.395(4)
_cell_measurement_reflns_used    887
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.8
_cell_volume                     776.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4678
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.9465
_exptl_absorpt_correction_T_min  0.9388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.480
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3267
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0928P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                2015
_reflns_number_total             3267
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5103.cif
_cod_data_source_block           I
_cod_database_code               2230595
_cod_database_fobs_code          2230595
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.05788(14) 1.03926(12) 1.12824(6) 0.0525(3) Uani d . 1 1 . .
N N1 0.2400(4) 0.5012(4) 1.03085(15) 0.0348(6) Uani d . 1 1 . .
N N2 0.2787(4) 0.5246(3) 0.94318(16) 0.0350(6) Uani d D 1 1 . .
N N3 0.1926(5) 0.3190(5) 1.36258(19) 0.0543(8) Uani d . 1 1 . .
O O1 0.3018(4) 0.2107(3) 0.93423(15) 0.0486(6) Uani d . 1 1 . .
O O2 0.2513(4) 0.8041(4) 0.63274(15) 0.0594(8) Uani d . 1 1 . .
O O3 0.2584(5) 0.1707(4) 1.33358(19) 0.0750(9) Uani d . 1 1 . .
O O4 0.1633(5) 0.3291(4) 1.44026(17) 0.0838(10) Uani d . 1 1 . .
O O5 0.4570(3) 0.8422(3) 0.90264(16) 0.0475(6) Uiso d D 1 1 . .
C C1 0.1635(4) 0.6554(4) 1.15934(19) 0.0322(7) Uani d . 1 1 . .
C C2 0.0887(4) 0.8238(4) 1.1940(2) 0.0350(7) Uani d . 1 1 . .
C C3 0.0387(5) 0.8259(5) 1.2810(2) 0.0435(8) Uani d . 1 1 . .
H H3 -0.0148 0.9392 1.3021 0.052 Uiso calc R 1 1 . .
C C4 0.0690(5) 0.6595(5) 1.3356(2) 0.0448(8) Uani d . 1 1 . .
H H4 0.0350 0.6582 1.3940 0.054 Uiso calc R 1 1 . .
C C5 0.1506(5) 0.4938(5) 1.3029(2) 0.0373(8) Uani d . 1 1 . .
C C6 0.1960(4) 0.4882(4) 1.2159(2) 0.0356(7) Uani d . 1 1 . .
H H6 0.2478 0.3738 1.1954 0.043 Uiso calc R 1 1 . .
C C7 0.2063(4) 0.6559(4) 1.0662(2) 0.0362(7) Uani d . 1 1 . .
H H7 0.2088 0.7708 1.0323 0.043 Uiso calc R 1 1 . .
C C8 0.3063(4) 0.3706(4) 0.8984(2) 0.0335(7) Uani d . 1 1 . .
C C9 0.3373(4) 0.4103(4) 0.8024(2) 0.0327(7) Uani d . 1 1 . .
C C10 0.2874(4) 0.5904(4) 0.7584(2) 0.0366(7) Uani d . 1 1 . .
H H10 0.2378 0.6916 0.7892 0.044 Uiso calc R 1 1 . .
C C11 0.3104(5) 0.6216(5) 0.6691(2) 0.0397(8) Uani d . 1 1 . .
C C12 0.3870(5) 0.4713(5) 0.6231(2) 0.0449(8) Uani d . 1 1 . .
H H12 0.4035 0.4907 0.5631 0.054 Uiso calc R 1 1 . .
C C13 0.4381(5) 0.2933(5) 0.6678(2) 0.0462(9) Uani d . 1 1 . .
H H13 0.4893 0.1925 0.6371 0.055 Uiso calc R 1 1 . .
C C14 0.4157(5) 0.2598(5) 0.7561(2) 0.0396(8) Uani d . 1 1 . .
H H14 0.4524 0.1383 0.7849 0.048 Uiso calc R 1 1 . .
C C15 0.2835(6) 0.8508(6) 0.5424(2) 0.0683(12) Uani d . 1 1 . .
H H15A 0.4162 0.8194 0.5312 0.103 Uiso calc R 1 1 . .
H H15B 0.2414 0.9844 0.5267 0.103 Uiso calc R 1 1 . .
H H15C 0.2148 0.7799 0.5083 0.103 Uiso calc R 1 1 . .
H H2 0.334(5) 0.624(4) 0.923(3) 0.080 Uiso d D 1 1 . .
H H5A 0.563(3) 0.822(5) 0.928(2) 0.080 Uiso d D 1 1 . .
H H5B 0.382(4) 0.931(4) 0.921(2) 0.080 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'
Cl Cl 0.1484 0.1585 '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
C7 N1 N2 . . 114.2(2) ?
C8 N2 N1 . . 119.0(2) ?
C8 N2 H2 . . 118(3) ?
N1 N2 H2 . . 118(3) ?
O3 N3 O4 . . 122.8(3) ?
O3 N3 C5 . . 119.1(3) ?
O4 N3 C5 . . 118.1(3) ?
C11 O2 C15 . . 118.6(3) ?
H5A O5 H5B . . 113(2) ?
C6 C1 C2 . . 117.9(3) ?
C6 C1 C7 . . 121.3(3) ?
C2 C1 C7 . . 120.8(3) ?
C3 C2 C1 . . 121.9(3) ?
C3 C2 Cl1 . . 117.9(2) ?
C1 C2 Cl1 . . 120.2(2) ?
C4 C3 C2 . . 119.4(3) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 119.1(3) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C4 C5 C6 . . 122.3(3) ?
C4 C5 N3 . . 118.8(3) ?
C6 C5 N3 . . 119.0(3) ?
C5 C6 C1 . . 119.3(3) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
N1 C7 C1 . . 121.0(3) ?
N1 C7 H7 . . 119.5 ?
C1 C7 H7 . . 119.5 ?
O1 C8 N2 . . 121.7(3) ?
O1 C8 C9 . . 122.8(3) ?
N2 C8 C9 . . 115.5(3) ?
C10 C9 C14 . . 119.4(3) ?
C10 C9 C8 . . 121.9(3) ?
C14 C9 C8 . . 118.7(3) ?
C9 C10 C11 . . 120.7(3) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
O2 C11 C10 . . 115.3(3) ?
O2 C11 C12 . . 124.9(3) ?
C10 C11 C12 . . 119.8(3) ?
C13 C12 C11 . . 118.9(3) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C14 C13 C12 . . 122.0(3) ?
C14 C13 H13 . . 119.0 ?
C12 C13 H13 . . 119.0 ?
C13 C14 C9 . . 119.2(3) ?
C13 C14 H14 . . 120.4 ?
C9 C14 H14 . . 120.4 ?
O2 C15 H15A . . 109.5 ?
O2 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O2 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
Cl1 C2 . 1.735(3) ?
N1 C7 . 1.275(4) ?
N1 N2 . 1.376(3) ?
N2 C8 . 1.351(4) ?
N2 H2 . 0.902(10) ?
N3 O3 . 1.219(4) ?
N3 O4 . 1.222(4) ?
N3 C5 . 1.461(4) ?
O1 C8 . 1.225(3) ?
O2 C11 . 1.365(4) ?
O2 C15 . 1.424(4) ?
O5 H5A . 0.837(10) ?
O5 H5B . 0.835(10) ?
C1 C6 . 1.391(4) ?
C1 C2 . 1.397(4) ?
C1 C7 . 1.467(4) ?
C2 C3 . 1.388(4) ?
C3 C4 . 1.370(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.380(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.381(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.499(4) ?
C9 C10 . 1.383(4) ?
C9 C14 . 1.396(4) ?
C10 C11 . 1.383(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.389(5) ?
C12 C13 . 1.376(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.369(5) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cg1 Cg2 3.712(3) . 2_665 y
Cg1 Cg2 3.672(3) . 2_765 y
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
N2 H2 O5 . 0.902(10) 1.922(13) 2.813(4) 169(4)
O5 H5B O1 1_565 0.835(10) 2.03(2) 2.783(3) 150(4)
O5 H5A O1 2_667 0.837(10) 2.30(3) 3.004(4) 142(3)
