#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/44/2224422.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_2224422
loop_
_publ_author_name
'Jin, Yan-Xian'
'Yan, Zhen-Zhong'
'Yang, Jian-Guo'
'Zhong, Ai-Guo'
'Pan, Fu-You'
_publ_section_title
;N'-[(E)-2-Hydroxybenzylidene]-5-methylisoxazole-4-carbohydrazide
 monohydrate
;
_journal_coeditor_code           RZ2385
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3113
_journal_paper_doi               10.1107/S1600536809048028
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H11 N3 O3, H2 O'
_chemical_formula_moiety         'C12 H11 N3 O3, H2 O'
_chemical_formula_sum            'C12 H13 N3 O4'
_chemical_formula_weight         263.25
_chemical_name_systematic
;N'-[(E)-2-Hydroxybenzylidene]-5-methylisoxazole-4-carbohydrazide
monohydrate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8783(6)
_cell_length_b                   11.3108(6)
_cell_length_c                   8.6535(4)
_cell_measurement_reflns_used    6440
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.40
_cell_volume                     1260.50(11)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12295
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9710
_exptl_absorpt_correction_T_min  0.9508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1432
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0725P)²+0.1350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                1279
_reflns_number_total             1432
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2385.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224422
_cod_database_fobs_code          2224422
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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_disorder_assembly
_atom_site_disorder_group
N N1 0.14390(16) -0.00283(18) 0.3335(3) 0.0565(5) Uani d . 1 . .
N N2 0.24031(12) 0.15708(15) 0.7518(2) 0.0421(4) Uani d . 1 . .
H H2B 0.1744 0.1523 0.7368 0.051 Uiso calc R 1 . .
N N3 0.27882(14) 0.20055(16) 0.8883(2) 0.0416(4) Uani d . 1 . .
O O1W 0.01706(11) 0.16789(14) 0.7294(2) 0.0559(4) Uani d D 1 . .
H H1W1 -0.026(2) 0.123(2) 0.776(4) 0.084 Uiso d D 1 . .
H H1W2 -0.019(2) 0.2255(19) 0.704(4) 0.084 Uiso d D 1 . .
O O1 0.24526(12) -0.01962(14) 0.2774(2) 0.0550(4) Uani d . 1 . .
O O2 0.40155(10) 0.13200(14) 0.6549(2) 0.0517(4) Uani d . 1 . .
O O3 0.43156(13) 0.25524(19) 1.0747(2) 0.0648(5) Uani d D 1 . .
C C1 0.26059(14) 0.06858(16) 0.5035(3) 0.0373(4) Uani d . 1 . .
C C2 0.15530(16) 0.0488(2) 0.4659(3) 0.0467(5) Uani d . 1 . .
H H2A 0.1002 0.0704 0.5294 0.056 Uiso calc R 1 . .
C C3 0.31271(16) 0.02328(18) 0.3808(3) 0.0442(5) Uani d . 1 . .
C C4 0.42389(18) 0.0114(3) 0.3423(4) 0.0716(8) Uani d . 1 . .
H H4A 0.4309 -0.0251 0.2427 0.107 Uiso calc R 1 . .
H H4B 0.4575 -0.0367 0.4189 0.107 Uiso calc R 1 . .
H H4C 0.4555 0.0882 0.3404 0.107 Uiso calc R 1 . .
C C5 0.30730(14) 0.12213(16) 0.6423(3) 0.0376(4) Uani d . 1 . .
C C6 0.25002(15) 0.27711(17) 1.1395(3) 0.0390(4) Uani d . 1 . .
C C7 0.35615(16) 0.29084(19) 1.1731(3) 0.0443(5) Uani d . 1 . .
C C8 0.3861(2) 0.3415(2) 1.3120(3) 0.0578(6) Uani d . 1 . .
H H8A 0.4563 0.3500 1.3347 0.069 Uiso calc R 1 . .
C C9 0.3126(2) 0.3794(2) 1.4164(3) 0.0583(6) Uani d . 1 . .
H H9A 0.3336 0.4143 1.5086 0.070 Uiso calc R 1 . .
C C10 0.2090(2) 0.3664(2) 1.3859(3) 0.0568(6) Uani d . 1 . .
H H10A 0.1598 0.3912 1.4576 0.068 Uiso calc R 1 . .
C C11 0.17799(17) 0.31606(19) 1.2483(3) 0.0488(5) Uani d . 1 . .
H H11A 0.1075 0.3080 1.2277 0.059 Uiso calc R 1 . .
C C12 0.21445(16) 0.22851(18) 0.9941(3) 0.0422(5) Uani d . 1 . .
H H12A 0.1437 0.2176 0.9776 0.051 Uiso calc R 1 . .
H H3A 0.403(2) 0.224(2) 0.994(3) 0.070(9) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C2 N1 O1 . . 105.15(19) ?
C5 N2 N3 . . 118.78(15) ?
C5 N2 H2B . . 120.6 ?
N3 N2 H2B . . 120.6 ?
C12 N3 N2 . . 118.15(17) ?
H1W1 O1W H1W2 . . 103(2) ?
C3 O1 N1 . . 108.85(18) ?
C7 O3 H3A . . 109(2) ?
C3 C1 C2 . . 103.6(2) ?
C3 C1 C5 . . 126.24(18) ?
C2 C1 C5 . . 130.1(2) ?
N1 C2 C1 . . 112.6(2) ?
N1 C2 H2A . . 123.7 ?
C1 C2 H2A . . 123.7 ?
O1 C3 C1 . . 109.82(18) ?
O1 C3 C4 . . 116.5(2) ?
C1 C3 C4 . . 133.7(2) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
O2 C5 N2 . . 123.2(2) ?
O2 C5 C1 . . 121.0(2) ?
N2 C5 C1 . . 115.76(15) ?
C11 C6 C7 . . 118.2(2) ?
C11 C6 C12 . . 119.79(19) ?
C7 C6 C12 . . 121.9(2) ?
O3 C7 C8 . . 118.0(2) ?
O3 C7 C6 . . 122.3(2) ?
C8 C7 C6 . . 119.7(2) ?
C9 C8 C7 . . 120.4(2) ?
C9 C8 H8A . . 119.8 ?
C7 C8 H8A . . 119.8 ?
C10 C9 C8 . . 120.7(2) ?
C10 C9 H9A . . 119.7 ?
C8 C9 H9A . . 119.7 ?
C9 C10 C11 . . 119.6(2) ?
C9 C10 H10A . . 120.2 ?
C11 C10 H10A . . 120.2 ?
C10 C11 C6 . . 121.4(2) ?
C10 C11 H11A . . 119.3 ?
C6 C11 H11A . . 119.3 ?
N3 C12 C6 . . 120.83(18) ?
N3 C12 H12A . . 119.6 ?
C6 C12 H12A . . 119.6 ?
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
N1 C2 . 1.294(3) ?
N1 O1 . 1.405(3) ?
N2 C5 . 1.341(3) ?
N2 N3 . 1.372(2) ?
N2 H2B . 0.8600 ?
N3 C12 . 1.274(3) ?
O1W H1W1 . 0.851(17) ?
O1W H1W2 . 0.831(17) ?
O1 C3 . 1.338(3) ?
O2 C5 . 1.224(2) ?
O3 C7 . 1.353(3) ?
O3 H3A . 0.864(18) ?
C1 C3 . 1.356(3) ?
C1 C2 . 1.412(3) ?
C1 C5 . 1.474(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.476(3) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C6 C11 . 1.393(3) ?
C6 C7 . 1.406(3) ?
C6 C12 . 1.448(3) ?
C7 C8 . 1.386(3) ?
C8 C9 . 1.377(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.368(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.379(4) ?
C10 H10A . 0.9300 ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
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
O3 H3A N3 . 0.87(3) 1.890(18) 2.617(2) 145(2)
N2 H2B O1W . 0.86 2.04 2.8847(17) 169.1
O1W H1W1 N1 2 0.85(3) 2.097(15) 2.9304(19) 166(2)
O1W H1W2 O2 3_455 0.831(15) 1.955(15) 2.7850(17) 176(2)
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
C5 N2 N3 C12 . . . . -176.93(18) ?
C2 N1 O1 C3 . . . . 0.1(2) ?
O1 N1 C2 C1 . . . . 0.2(2) ?
C3 C1 C2 N1 . . . . -0.3(2) ?
C5 C1 C2 N1 . . . . -178.83(19) ?
N1 O1 C3 C1 . . . . -0.3(2) ?
N1 O1 C3 C4 . . . . 179.0(2) ?
C2 C1 C3 O1 . . . . 0.3(2) ?
C5 C1 C3 O1 . . . . 178.94(17) ?
C2 C1 C3 C4 . . . . -178.7(3) ?
C5 C1 C3 C4 . . . . -0.1(4) ?
N3 N2 C5 O2 . . . . -3.5(3) ?
N3 N2 C5 C1 . . . . 175.77(16) ?
C3 C1 C5 O2 . . . . 1.7(3) ?
C2 C1 C5 O2 . . . . 179.9(2) ?
C3 C1 C5 N2 . . . . -177.57(19) ?
C2 C1 C5 N2 . . . . 0.6(3) ?
C11 C6 C7 O3 . . . . 179.8(2) ?
C12 C6 C7 O3 . . . . -2.7(3) ?
C11 C6 C7 C8 . . . . 0.3(3) ?
C12 C6 C7 C8 . . . . 177.8(2) ?
O3 C7 C8 C9 . . . . 179.9(2) ?
C6 C7 C8 C9 . . . . -0.6(4) ?
C7 C8 C9 C10 . . . . 0.9(4) ?
C8 C9 C10 C11 . . . . -0.8(4) ?
C9 C10 C11 C6 . . . . 0.6(4) ?
C7 C6 C11 C10 . . . . -0.3(3) ?
C12 C6 C11 C10 . . . . -177.9(2) ?
N2 N3 C12 C6 . . . . -178.73(16) ?
C11 C6 C12 N3 . . . . 174.73(19) ?
C7 C6 C12 N3 . . . . -2.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655958
