#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/70/2207013.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_2207013
loop_
_publ_author_name
'Ali, Hapipah M.'
'Puvaneswary, Subramaniam'
'Ng, Seik Weng'
_publ_section_title
;
 5-Nitrosalicylaldehyde benzoylhydrazone
;
_journal_coeditor_code           LH6505
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3464
_journal_page_last               o3465
_journal_paper_doi               10.1107/S1600536805030497
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H11 N3 O4'
_chemical_formula_moiety         'C14 H11 N3 O4'
_chemical_formula_sum            'C14 H11 N3 O4'
_chemical_formula_weight         285.26
_chemical_name_systematic
;
5-Nitrosalicylaldehyde benzoylhydrazone
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c 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                   30.224(2)
_cell_length_b                   4.8017(3)
_cell_length_c                   8.7257(6)
_cell_measurement_reflns_used    2819
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.7
_cell_measurement_theta_min      2.3
_cell_volume                     1266.33(14)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker SMART area-detector'
_diffrn_measurement_method       'φ and 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  0.030
_diffrn_reflns_av_sigmaI/netI    0.024
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7031
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.04
_diffrn_reflns_theta_min         1.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.17
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         1478
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.17
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_gt           0.035
_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)+(0.0699P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.088
_refine_ls_wR_factor_ref         0.113
_reflns_number_gt                1226
_reflns_number_total             1478
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6505.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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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_original_cell_volume        1266.3(2)
_cod_database_code               2207013
_cod_database_fobs_code          2207013
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
loop_
_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_type_symbol
O1 0.29060(10) 1.1454(5) 0.5000(3) 0.0397(5) Uani d D 1 O
O2 0.40150(10) 0.3332(5) 0.9011(3) 0.0577(7) Uani d . 1 O
O3 0.33600(10) 0.2125(5) 0.9692(3) 0.0482(6) Uani d . 1 O
O4 0.14050(10) 0.3305(5) 0.8318(3) 0.0446(6) Uani d . 1 O
N1 0.36130(10) 0.3571(5) 0.8939(3) 0.0354(6) Uani d . 1 N
N2 0.20580(10) 0.6635(5) 0.7303(3) 0.0347(6) Uani d . 1 N
N3 0.16150(10) 0.7313(5) 0.7190(3) 0.0363(6) Uani d D 1 N
C1 0.30900(10) 0.9580(6) 0.5940(3) 0.0310(6) Uani d . 1 C
C2 0.35440(10) 0.9159(6) 0.6027(4) 0.0386(7) Uani d . 1 C
C3 0.37170(10) 0.7189(6) 0.7006(4) 0.0379(7) Uani d . 1 C
C4 0.34300(10) 0.5641(6) 0.7914(3) 0.0323(6) Uani d . 1 C
C5 0.29770(10) 0.6014(6) 0.7856(3) 0.0326(6) Uani d . 1 C
C6 0.28010(10) 0.7982(6) 0.6866(4) 0.0323(6) Uani d . 1 C
C7 0.23220(10) 0.8434(6) 0.6768(4) 0.0361(7) Uani d . 1 C
C8 0.13080(10) 0.5552(6) 0.7721(3) 0.0334(6) Uani d . 1 C
C9 0.08370(10) 0.6415(6) 0.7545(4) 0.0335(6) Uani d . 1 C
C10 0.05210(10) 0.5096(7) 0.8425(4) 0.0465(8) Uani d . 1 C
C11 0.00790(10) 0.5788(8) 0.8292(5) 0.0522(9) Uani d . 1 C
C12 -0.00490(10) 0.7793(8) 0.7268(5) 0.0518(9) Uani d . 1 C
C13 0.02610(10) 0.9103(8) 0.6383(5) 0.0527(9) Uani d . 1 C
C14 0.07020(10) 0.8433(6) 0.6504(4) 0.0437(8) Uani d . 1 C
H1o 0.3110(10) 1.223(7) 0.447(4) 0.050(10) Uiso d D 1 H
H3n 0.1530(10) 0.891(4) 0.689(4) 0.040(10) Uiso d D 1 H
H2 0.3733 1.0215 0.5419 0.046 Uiso calc R 1 H
H3 0.4021 0.6899 0.7059 0.046 Uiso calc R 1 H
H5 0.2792 0.4954 0.8476 0.039 Uiso calc R 1 H
H7 0.2213 1.0043 0.6312 0.043 Uiso calc R 1 H
H10 0.0607 0.3724 0.9117 0.056 Uiso calc R 1 H
H11 -0.0131 0.4895 0.8897 0.063 Uiso calc R 1 H
H12 -0.0346 0.8263 0.7175 0.062 Uiso calc R 1 H
H13 0.0172 1.0464 0.5690 0.063 Uiso calc R 1 H
H14 0.0909 0.9331 0.5891 0.052 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0380(10) 0.0410(10) 0.0410(10) -0.0010(10) 0.0020(10) 0.0120(10)
O2 0.0320(10) 0.070(2) 0.071(2) 0.0030(10) -0.0070(10) 0.025(2)
O3 0.0450(10) 0.0510(10) 0.0480(10) 0.0010(10) 0.0010(10) 0.0200(10)
O4 0.0390(10) 0.0370(10) 0.0580(10) 0.0010(10) -0.0030(10) 0.0180(10)
N1 0.0370(10) 0.0350(10) 0.0350(10) 0.0020(10) -0.0010(10) 0.0030(10)
N2 0.0290(10) 0.0340(10) 0.0410(10) 0.0030(10) 0.0000(10) 0.0020(10)
N3 0.0300(10) 0.0300(10) 0.048(2) 0.0020(10) 0.0010(10) 0.0100(10)
C1 0.036(2) 0.0270(10) 0.0310(10) -0.0020(10) 0.0010(10) 0.0000(10)
C2 0.037(2) 0.040(2) 0.0390(10) -0.0060(10) 0.0080(10) 0.003(2)
C3 0.030(2) 0.042(2) 0.0420(10) 0.0000(10) 0.0020(10) 0.003(2)
C4 0.0330(10) 0.032(2) 0.0320(10) -0.0010(10) -0.0020(10) 0.0000(10)
C5 0.0330(10) 0.033(2) 0.0320(10) -0.0050(10) 0.0020(10) 0.0020(10)
C6 0.0310(10) 0.032(2) 0.0330(10) -0.0020(10) 0.0010(10) 0.0000(10)
C7 0.033(2) 0.035(2) 0.0410(10) 0.0020(10) -0.0010(10) 0.0060(10)
C8 0.0330(10) 0.030(2) 0.0360(10) -0.0010(10) -0.0010(10) 0.0000(10)
C9 0.0290(10) 0.035(2) 0.0370(10) -0.0020(10) 0.0000(10) 0.0010(10)
C10 0.042(2) 0.045(2) 0.0530(10) 0.0040(10) 0.005(2) 0.015(2)
C11 0.037(2) 0.060(2) 0.060(2) -0.001(2) 0.011(2) 0.007(2)
C12 0.032(2) 0.059(2) 0.064(3) 0.0070(10) -0.001(2) -0.006(2)
C13 0.045(2) 0.056(2) 0.057(2) 0.008(2) -0.006(2) 0.017(2)
C14 0.036(2) 0.046(2) 0.050(2) -0.0020(10) -0.0020(10) 0.013(2)
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
_geom_angle_publ_flag
C1 O1 H1o 109(2) no
O2 N1 O3 122.8(3) no
O2 N1 C4 118.5(2) no
O3 N1 C4 118.8(2) no
C7 N2 N3 115.2(2) no
C8 N3 N2 119.9(2) no
O1 C1 C2 122.8(3) no
O1 C1 C6 117.1(2) no
C2 C1 C6 120.0(3) no
C3 C2 C1 120.6(3) no
C2 C3 C4 119.0(3) no
C5 C4 C3 121.9(3) no
C5 C4 N1 119.4(2) no
C3 C4 N1 118.7(2) no
C4 C5 C6 119.5(3) no
C5 C6 C1 119.1(3) no
C5 C6 C7 121.1(3) no
C1 C6 C7 119.8(3) no
N2 C7 C6 120.0(3) no
O4 C8 N3 122.3(3) no
O4 C8 C9 120.9(3) no
N3 C8 C9 116.8(3) no
C10 C9 C14 118.7(3) no
C10 C9 C8 118.4(3) no
C14 C9 C8 122.9(3) no
C9 C10 C11 120.8(3) no
C12 C11 C10 119.8(3) no
C13 C12 C11 119.9(3) no
C12 C13 C14 120.9(3) no
C13 C14 C9 119.9(3) no
C8 N3 H3n 118(2) no
N2 N3 H3n 122(2) no
C3 C2 H2 119.7 no
C1 C2 H2 119.7 no
C2 C3 H3 120.5 no
C4 C3 H3 120.5 no
C4 C5 H5 120.2 no
C6 C5 H5 120.2 no
N2 C7 H7 120.0 no
C6 C7 H7 120.0 no
C9 C10 H10 119.6 no
C11 C10 H10 119.6 no
C12 C11 H11 120.1 no
C10 C11 H11 120.1 no
C13 C12 H12 120.0 no
C11 C12 H12 120.0 no
C12 C13 H13 119.6 no
C14 C13 H13 119.6 no
C13 C14 H14 120.0 no
C9 C14 H14 120.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.339(4) no
O2 N1 1.221(3) no
O3 N1 1.225(3) no
O4 C8 1.233(3) no
N1 C4 1.447(4) no
N2 C7 1.266(4) no
N2 N3 1.382(3) no
N3 C8 1.338(4) no
C1 C2 1.388(4) no
C1 C6 1.417(4) no
C2 C3 1.377(5) no
C3 C4 1.390(4) no
C4 C5 1.381(4) no
C5 C6 1.387(4) no
C6 C7 1.464(4) no
C8 C9 1.489(4) no
C9 C10 1.380(4) no
C9 C14 1.390(4) no
C10 C11 1.382(5) no
C11 C12 1.369(6) no
C12 C13 1.367(5) no
C13 C14 1.375(4) no
O1 H1o 0.850(10) no
N3 H3n 0.850(10) no
C2 H2 0.93 no
C3 H3 0.93 no
C5 H5 0.93 no
C7 H7 0.93 no
C10 H10 0.93 no
C11 H11 0.93 no
C12 H12 0.93 no
C13 H13 0.93 no
C14 H14 0.93 no
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
_geom_hbond_publ_flag
O1 H1o O4 3_564 0.850(10) 1.860(10) 2.700(3) 170(3) yes
N3 H3n O3 3_564 0.850(10) 2.48(2) 3.178(3) 140(3) yes
N3 H3n O4 1_565 0.850(10) 2.48(3) 3.106(4) 131(3) yes
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
_geom_torsion_publ_flag
C7 N2 N3 C8 180.0(3) no
O1 C1 C2 C3 -179.5(3) no
C6 C1 C2 C3 0.1(5) no
C1 C2 C3 C4 -0.4(5) no
C2 C3 C4 C5 0.3(5) no
C2 C3 C4 N1 179.9(3) no
O2 N1 C4 C5 -177.7(3) no
O3 N1 C4 C5 2.7(4) no
O2 N1 C4 C3 2.7(4) no
O3 N1 C4 C3 -176.9(3) no
C3 C4 C5 C6 0.1(4) no
N1 C4 C5 C6 -179.5(3) no
C4 C5 C6 C1 -0.4(4) no
C4 C5 C6 C7 179.8(3) no
O1 C1 C6 C5 179.9(3) no
C2 C1 C6 C5 0.2(4) no
O1 C1 C6 C7 -0.2(4) no
C2 C1 C6 C7 -179.9(3) no
N3 N2 C7 C6 178.1(3) no
C5 C6 C7 N2 -16.5(5) no
C1 C6 C7 N2 163.7(3) no
N2 N3 C8 O4 0.0(4) no
N2 N3 C8 C9 -179.4(3) no
O4 C8 C9 C10 18.2(4) no
N3 C8 C9 C10 -162.4(3) no
O4 C8 C9 C14 -160.0(3) no
N3 C8 C9 C14 19.4(4) no
C14 C9 C10 C11 -0.8(5) no
C8 C9 C10 C11 -179.1(3) no
C9 C10 C11 C12 0.4(6) no
C10 C11 C12 C13 -0.1(6) no
C11 C12 C13 C14 0.1(6) no
C12 C13 C14 C9 -0.4(6) no
C10 C9 C14 C13 0.8(5) no
C8 C9 C14 C13 179.0(3) no
