#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/08/2210804.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_2210804
loop_
_publ_author_name
'Qiu, Xiao-Yang'
'Luo Qiu-Yan'
'Yang, Sen-Lin'
'Liu, Wei-Sheng'
_publ_section_title
;
 (E)-2-Hydroxy-N'-[1-(4-methoxyphenyl)ethylidene]benzohydrazide
;
_journal_coeditor_code           WK2022
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4291
_journal_page_last               o4292
_journal_paper_doi               10.1107/S1600536806029345
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H16 N2 O3'
_chemical_formula_moiety         'C16 H16 N2 O3'
_chemical_formula_sum            'C16 H16 N2 O3'
_chemical_formula_weight         284.31
_chemical_name_systematic
;
(E)-2-hydroxy-N'-[1-(4-methoxyphenyl)ethylidene]benzohydrazide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   7.4007(15)
_cell_length_b                   11.794(2)
_cell_length_c                   16.290(3)
_cell_measurement_reflns_used    1678
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      4.2
_cell_volume                     1421.9(5)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10760
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.115
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0353
_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)+(0.0368P)²+0.1085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                1341
_reflns_number_total             1992
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wk2022.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_original_cell_volume        1421.8(5)
_cod_database_code               2210804
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
N N1 1.0333(3) 0.84602(14) 0.35529(10) 0.0624(5) Uani d . 1
H H1 0.9991 0.7776 0.3455 0.075 Uiso calc R 1
O O1 0.9267(3) 0.69682(13) 0.24793(9) 0.0787(5) Uani d . 1
H H1A 0.8824 0.6399 0.2272 0.118 Uiso calc R 1
C C1 1.0049(3) 0.76118(18) 0.18847(12) 0.0594(5) Uani d . 1
O O2 1.1725(3) 1.00287(13) 0.30866(9) 0.0704(5) Uani d . 1
N N2 1.0173(3) 0.89007(15) 0.43330(10) 0.0632(5) Uani d . 1
C C2 0.9985(4) 0.7269(2) 0.10669(13) 0.0692(6) Uani d . 1
H H2 0.9400 0.6599 0.0925 0.083 Uiso calc R 1
C C3 1.0786(4) 0.7921(2) 0.04704(14) 0.0766(7) Uani d . 1
H H3 1.0742 0.7686 -0.0074 0.092 Uiso calc R 1
O O4 0.8539(3) 1.01502(19) 0.80026(10) 0.0977(7) Uani d . 1
C C4 1.1651(4) 0.8917(2) 0.06683(13) 0.0763(7) Uani d . 1
H H4 1.2190 0.9355 0.0261 0.092 Uiso calc R 1
C C5 1.1711(3) 0.9258(2) 0.14772(14) 0.0670(6) Uani d . 1
H H5 1.2301 0.9929 0.1611 0.080 Uiso calc R 1
C C6 1.0911(3) 0.86257(17) 0.20981(12) 0.0551(5) Uani d . 1
C C7 1.1016(3) 0.90927(18) 0.29476(12) 0.0578(5) Uani d . 1
C C8 0.9673(3) 0.81891(19) 0.48914(13) 0.0577(5) Uani d . 1
C C9 0.9376(3) 0.86631(18) 0.57170(13) 0.0590(5) Uani d . 1
C C10 0.9631(3) 0.8029(2) 0.64255(13) 0.0680(6) Uani d . 1
H H10 0.9977 0.7273 0.6381 0.082 Uiso calc R 1
C C11 0.9382(4) 0.8497(2) 0.71964(14) 0.0737(7) Uani d . 1
H H11 0.9585 0.8061 0.7663 0.088 Uiso calc R 1
C C12 0.8831(4) 0.9611(2) 0.72732(14) 0.0715(7) Uani d . 1
C C13 0.8561(4) 1.0251(2) 0.65774(15) 0.0750(7) Uani d . 1
H H13 0.8190 1.1002 0.6625 0.090 Uiso calc R 1
C C14 0.8836(3) 0.9789(2) 0.58119(13) 0.0661(6) Uani d . 1
H H14 0.8659 1.0236 0.5349 0.079 Uiso calc R 1
C C15 0.8983(5) 0.9563(3) 0.87323(15) 0.1013(10) Uani d . 1
H H15A 0.8289 0.8877 0.8764 0.152 Uiso calc R 1
H H15B 0.8713 1.0033 0.9198 0.152 Uiso calc R 1
H H15C 1.0247 0.9382 0.8731 0.152 Uiso calc R 1
C C16 0.9374(4) 0.69470(19) 0.47364(15) 0.0727(7) Uani d . 1
H H16A 0.8401 0.6852 0.4352 0.109 Uiso calc R 1
H H16B 0.9072 0.6577 0.5243 0.109 Uiso calc R 1
H H16C 1.0456 0.6619 0.4515 0.109 Uiso calc R 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
C7 N1 N2 120.18(17)
C7 N1 H1 119.9
N2 N1 H1 119.9
C1 O1 H1A 109.5
O1 C1 C2 120.3(2)
O1 C1 C6 119.61(17)
C2 C1 C6 120.1(2)
C8 N2 N1 115.41(17)
C3 C2 C1 119.9(2)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 120.9(2)
C2 C3 H3 119.6
C4 C3 H3 119.6
C12 O4 C15 117.8(2)
C3 C4 C5 119.2(2)
C3 C4 H4 120.4
C5 C4 H4 120.4
C4 C5 C6 121.7(2)
C4 C5 H5 119.1
C6 C5 H5 119.1
C5 C6 C1 118.17(19)
C5 C6 C7 117.08(19)
C1 C6 C7 124.74(19)
O2 C7 N1 121.42(19)
O2 C7 C6 121.26(19)
N1 C7 C6 117.31(19)
N2 C8 C9 116.05(19)
N2 C8 C16 123.9(2)
C9 C8 C16 120.1(2)
C10 C9 C14 117.4(2)
C10 C9 C8 122.3(2)
C14 C9 C8 120.3(2)
C11 C10 C9 121.4(2)
C11 C10 H10 119.3
C9 C10 H10 119.3
C12 C11 C10 120.1(2)
C12 C11 H11 120.0
C10 C11 H11 120.0
O4 C12 C13 116.0(2)
O4 C12 C11 124.7(2)
C13 C12 C11 119.3(2)
C14 C13 C12 120.5(2)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C9 121.3(2)
C13 C14 H14 119.3
C9 C14 H14 119.3
O4 C15 H15A 109.5
O4 C15 H15B 109.5
H15A C15 H15B 109.5
O4 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C8 C16 H16A 109.5
C8 C16 H16B 109.5
H16A C16 H16B 109.5
C8 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.336(3)
N1 N2 1.378(2)
N1 H1 0.8600
O1 C1 1.360(3)
O1 H1A 0.8200
C1 C2 1.393(3)
C1 C6 1.399(3)
O2 C7 1.243(3)
N2 C8 1.292(3)
C2 C3 1.374(3)
C2 H2 0.9300
C3 C4 1.377(4)
C3 H3 0.9300
O4 C12 1.365(3)
O4 C15 1.414(3)
C4 C5 1.378(3)
C4 H4 0.9300
C5 C6 1.389(3)
C5 H5 0.9300
C6 C7 1.491(3)
C8 C9 1.473(3)
C8 C16 1.503(3)
C9 C10 1.388(3)
C9 C14 1.395(3)
C10 C11 1.384(3)
C10 H10 0.9300
C11 C12 1.381(4)
C11 H11 0.9300
C12 C13 1.377(3)
C13 C14 1.376(3)
C13 H13 0.9300
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 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
N1 H1 O1 . 0.86 1.93 2.603(2) 134.2
O1 H1A O2 3_745 0.82 1.77 2.573(2) 167.8
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
C7 N1 N2 C8 -173.2(2)
O1 C1 C2 C3 -179.7(2)
C6 C1 C2 C3 0.7(4)
C1 C2 C3 C4 -0.2(4)
C2 C3 C4 C5 0.1(4)
C3 C4 C5 C6 -0.3(4)
C4 C5 C6 C1 0.8(3)
C4 C5 C6 C7 -178.4(2)
O1 C1 C6 C5 179.4(2)
C2 C1 C6 C5 -1.0(3)
O1 C1 C6 C7 -1.5(3)
C2 C1 C6 C7 178.1(2)
N2 N1 C7 O2 9.0(3)
N2 N1 C7 C6 -171.57(18)
C5 C6 C7 O2 2.8(3)
C1 C6 C7 O2 -176.3(2)
C5 C6 C7 N1 -176.6(2)
C1 C6 C7 N1 4.3(3)
N1 N2 C8 C9 -175.98(19)
N1 N2 C8 C16 3.3(3)
N2 C8 C9 C10 -150.6(2)
C16 C8 C9 C10 30.0(3)
N2 C8 C9 C14 28.7(3)
C16 C8 C9 C14 -150.6(2)
C14 C9 C10 C11 -0.7(4)
C8 C9 C10 C11 178.6(2)
C9 C10 C11 C12 1.3(4)
C15 O4 C12 C13 -173.5(2)
C15 O4 C12 C11 5.9(4)
C10 C11 C12 O4 179.7(3)
C10 C11 C12 C13 -0.9(4)
O4 C12 C13 C14 179.4(2)
C11 C12 C13 C14 0.0(4)
C12 C13 C14 C9 0.7(4)
C10 C9 C14 C13 -0.3(4)
C8 C9 C14 C13 -179.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7858942
