##############################################################################
### ###
### Electronic paper (Acta Crystallographica Section E) ###
### ###
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# #
# This CIF contains the data in a paper accepted for publication in Acta #
# Crystallographica Section E. It conforms to the requirements of Notes #
# for Authors for Section E, and has been peer reviewed under the auspices #
# of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. #
# #
# Software is freely available for graphical display of the structure(s) in #
# this CIF. For information consult the CIF home page http://www.iucr.org/ #
# cif/home.html #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
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data_global
_audit_creation_method 'form.cif (version 2.0)'
_journal_data_validation_number ?
_journal_date_recd_electronic 2010-03-16
_journal_date_accepted 2010-03-17
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2010
_journal_volume 66
_journal_issue 4
_journal_page_first o892
_journal_page_last o892
_journal_paper_category QO
_journal_coeditor_code BX2271
_publ_contact_author_name 'Feng Zhi'
_publ_contact_author_address
;
Modern Medical Research Center
Third Affiliated Hospital of Soochow University
Changzhou 213003
People's Republic of China
;
_publ_contact_author_email czfph@126.com
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_section_title
;
N'-(2-Hydroxy-4-methoxybenzylidene)isonicotinohydrazide
;
loop_
_publ_author_name
_publ_author_address
'Feng Zhi'
;
Modern Medical Research Center
Third Affiliated Hospital of Soochow University
Changzhou 213003
People's Republic of China
;
'Rong Wang'
;
Modern Medical Research Center
Third Affiliated Hospital of Soochow University
Changzhou 213003
People's Republic of China
;
_publ_section_synopsis .
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N'-(2-Hydroxy-4-methoxybenzylidene)isonicotinohydrazide
;
_chemical_name_common ?
_chemical_formula_moiety 'C14 H13 N3 O3'
_chemical_formula_sum 'C14 H13 N3 O3'
_chemical_formula_iupac 'C14 H13 N3 O3'
_chemical_formula_weight 271.27
_chemical_melting_point ?
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
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'
_cell_length_a 8.4704(11)
_cell_length_b 10.6866(15)
_cell_length_c 14.848(2)
_cell_angle_alpha 90.00
_cell_angle_beta 104.929(5)
_cell_angle_gamma 90.00
_cell_volume 1298.7(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2534
_cell_measurement_theta_min 2.4
_cell_measurement_theta_max 29.9
_cell_measurement_temperature 298(2)
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.17
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.15
_exptl_crystal_density_diffrn 1.387
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 568
_exptl_absorpt_coefficient_mu 0.100
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min 0.9832
_exptl_absorpt_correction_T_max 0.9851
_exptl_special_details
;
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 7591
_diffrn_reflns_av_R_equivalents 0.0208
_diffrn_reflns_av_sigmaI/netI 0.0235
_diffrn_reflns_theta_min 2.38
_diffrn_reflns_theta_max 27.00
_diffrn_reflns_theta_full 27.00
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 14
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors
based on F^2^ are statistically about twice as large as those based on
F, and R- factors based on ALL data will be even larger.
;
_reflns_number_total 2814
_reflns_number_gt 2148
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0541
_refine_ls_R_factor_gt 0.0397
_refine_ls_wR_factor_gt 0.0979
_refine_ls_wR_factor_ref 0.1072
_refine_ls_goodness_of_fit_ref 1.045
_refine_ls_restrained_S_all 1.045
_refine_ls_number_reflns 2814
_refine_ls_number_parameters 186
_refine_ls_number_restraints 1
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.2097P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.148
_refine_diff_density_min -0.174
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
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'
_computing_data_collection 'SMART (Bruker, 2002)'
_computing_cell_refinement 'SAINT (Bruker, 2002)'
_computing_data_reduction 'SAINT (Bruker, 2002)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
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 0.10385(14) 0.87232(11) 0.12848(8) 0.0425(3) Uani d . 1 . .
N N2 0.01859(14) 0.78408(11) 0.16392(8) 0.0422(3) Uani d D 1 . .
N N3 -0.26459(16) 0.40486(11) 0.24523(9) 0.0491(3) Uani d . 1 . .
O O1 0.28189(15) 0.93517(9) 0.01927(8) 0.0554(3) Uani d . 1 . .
H H1 0.2284 0.8881 0.0436 0.083 Uiso calc R 1 . .
O O2 0.12526(15) 0.62775(10) 0.09488(9) 0.0624(3) Uani d . 1 . .
O O3 0.40498(14) 1.36738(9) 0.00218(8) 0.0550(3) Uani d . 1 . .
C C1 0.17894(16) 1.08276(12) 0.11284(10) 0.0404(3) Uani d . 1 . .
C C2 0.26792(16) 1.05413(12) 0.04800(9) 0.0386(3) Uani d . 1 . .
C C3 0.34625(17) 1.14692(12) 0.01077(10) 0.0410(3) Uani d . 1 . .
H H3 0.4072 1.1263 -0.0310 0.049 Uiso calc R 1 . .
C C4 0.33345(17) 1.27035(12) 0.03599(10) 0.0421(3) Uani d . 1 . .
C C5 0.24469(19) 1.30187(14) 0.09935(12) 0.0518(4) Uani d . 1 . .
H H5 0.2356 1.3850 0.1159 0.062 Uiso calc R 1 . .
C C6 0.17066(19) 1.20882(14) 0.13711(11) 0.0512(4) Uani d . 1 . .
H H6 0.1129 1.2301 0.1803 0.061 Uiso calc R 1 . .
C C7 0.09706(17) 0.98671(13) 0.15257(10) 0.0446(3) Uani d . 1 . .
H H7 0.0393 1.0082 0.1958 0.054 Uiso calc R 1 . .
C C8 0.03539(16) 0.66264(13) 0.14180(9) 0.0410(3) Uani d . 1 . .
C C9 -0.06727(16) 0.57305(12) 0.17959(9) 0.0365(3) Uani d . 1 . .
C C10 -0.12509(18) 0.46540(13) 0.13050(10) 0.0437(3) Uani d . 1 . .
H H10 -0.0990 0.4472 0.0748 0.052 Uiso calc R 1 . .
C C11 -0.22227(19) 0.38542(14) 0.16569(11) 0.0493(4) Uani d . 1 . .
H H11 -0.2607 0.3135 0.1319 0.059 Uiso calc R 1 . .
C C12 -0.20463(18) 0.50811(13) 0.29267(10) 0.0454(3) Uani d . 1 . .
H H12 -0.2304 0.5231 0.3489 0.054 Uiso calc R 1 . .
C C13 -0.10710(17) 0.59344(12) 0.26321(9) 0.0395(3) Uani d . 1 . .
H H13 -0.0684 0.6638 0.2989 0.047 Uiso calc R 1 . .
C C14 0.4899(2) 1.34231(15) -0.06713(12) 0.0585(4) Uani d . 1 . .
H H14A 0.5817 1.2890 -0.0415 0.088 Uiso calc R 1 . .
H H14B 0.5276 1.4196 -0.0873 0.088 Uiso calc R 1 . .
H H14C 0.4177 1.3015 -0.1193 0.088 Uiso calc R 1 . .
H H2 -0.0540(19) 0.8096(18) 0.1945(12) 0.080 Uiso d D 1 . .
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
N1 0.0453(7) 0.0384(6) 0.0492(7) -0.0015(5) 0.0219(5) 0.0052(5)
N2 0.0459(7) 0.0376(6) 0.0506(7) -0.0014(5) 0.0261(5) 0.0030(5)
N3 0.0577(8) 0.0419(7) 0.0544(7) -0.0031(6) 0.0266(6) 0.0045(6)
O1 0.0798(8) 0.0316(5) 0.0704(7) -0.0041(5) 0.0477(6) -0.0036(5)
O2 0.0732(7) 0.0502(6) 0.0831(8) -0.0044(5) 0.0549(7) -0.0083(6)
O3 0.0653(7) 0.0335(5) 0.0721(7) -0.0032(5) 0.0281(6) 0.0067(5)
C1 0.0385(7) 0.0357(7) 0.0496(8) 0.0020(6) 0.0161(6) 0.0012(6)
C2 0.0426(7) 0.0323(7) 0.0424(7) 0.0012(5) 0.0135(6) 0.0006(6)
C3 0.0459(7) 0.0371(7) 0.0429(7) 0.0003(6) 0.0167(6) 0.0019(6)
C4 0.0420(7) 0.0330(7) 0.0497(8) 0.0006(6) 0.0091(6) 0.0053(6)
C5 0.0568(9) 0.0310(7) 0.0722(10) 0.0026(6) 0.0247(8) -0.0039(7)
C6 0.0523(9) 0.0426(8) 0.0665(10) 0.0040(6) 0.0294(8) -0.0051(7)
C7 0.0439(8) 0.0442(8) 0.0516(8) 0.0013(6) 0.0230(7) 0.0001(6)
C8 0.0429(7) 0.0412(8) 0.0436(7) 0.0006(6) 0.0198(6) 0.0002(6)
C9 0.0361(7) 0.0347(7) 0.0416(7) 0.0045(5) 0.0155(6) 0.0028(5)
C10 0.0521(8) 0.0404(7) 0.0445(8) 0.0008(6) 0.0231(7) -0.0031(6)
C11 0.0574(9) 0.0406(8) 0.0541(9) -0.0066(7) 0.0217(7) -0.0048(7)
C12 0.0557(9) 0.0456(8) 0.0408(8) 0.0036(7) 0.0231(7) 0.0041(6)
C13 0.0461(8) 0.0366(7) 0.0380(7) 0.0019(6) 0.0148(6) -0.0003(6)
C14 0.0664(10) 0.0444(9) 0.0713(11) -0.0039(7) 0.0301(9) 0.0107(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C7 . 1.2791(18) ?
N1 N2 . 1.3724(15) ?
N2 C8 . 1.3552(18) ?
N2 H2 . 0.896(9) ?
N3 C11 . 1.3358(19) ?
N3 C12 . 1.3369(19) ?
O1 C2 . 1.3558(16) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.2153(16) ?
O3 C4 . 1.3606(16) ?
O3 C14 . 1.4247(19) ?
C1 C6 . 1.401(2) ?
C1 C2 . 1.4009(19) ?
C1 C7 . 1.4468(19) ?
C2 C3 . 1.3849(19) ?
C3 C4 . 1.3831(19) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.388(2) ?
C5 C6 . 1.370(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.4963(18) ?
C9 C10 . 1.3823(19) ?
C9 C13 . 1.3852(18) ?
C10 C11 . 1.379(2) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.3753(19) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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 . . 118.91(12) ?
C8 N2 N1 . . 117.81(11) ?
C8 N2 H2 . . 122.9(13) ?
N1 N2 H2 . . 118.9(13) ?
C11 N3 C12 . . 116.24(12) ?
C2 O1 H1 . . 109.5 ?
C4 O3 C14 . . 118.62(11) ?
C6 C1 C2 . . 117.28(13) ?
C6 C1 C7 . . 121.09(13) ?
C2 C1 C7 . . 121.63(12) ?
O1 C2 C3 . . 117.14(12) ?
O1 C2 C1 . . 121.81(12) ?
C3 C2 C1 . . 121.05(12) ?
C4 C3 C2 . . 119.72(13) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
O3 C4 C3 . . 123.60(13) ?
O3 C4 C5 . . 115.81(12) ?
C3 C4 C5 . . 120.58(13) ?
C6 C5 C4 . . 119.07(13) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C5 C6 C1 . . 122.28(14) ?
C5 C6 H6 . . 118.9 ?
C1 C6 H6 . . 118.9 ?
N1 C7 C1 . . 120.22(13) ?
N1 C7 H7 . . 119.9 ?
C1 C7 H7 . . 119.9 ?
O2 C8 N2 . . 123.59(13) ?
O2 C8 C9 . . 121.93(13) ?
N2 C8 C9 . . 114.48(11) ?
C10 C9 C13 . . 117.94(12) ?
C10 C9 C8 . . 119.73(12) ?
C13 C9 C8 . . 122.33(12) ?
C11 C10 C9 . . 118.74(13) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
N3 C11 C10 . . 124.11(14) ?
N3 C11 H11 . . 117.9 ?
C10 C11 H11 . . 117.9 ?
N3 C12 C13 . . 123.88(13) ?
N3 C12 H12 . . 118.1 ?
C13 C12 H12 . . 118.1 ?
C12 C13 C9 . . 119.06(13) ?
C12 C13 H13 . . 120.5 ?
C9 C13 H13 . . 120.5 ?
O3 C14 H14A . . 109.5 ?
O3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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 N3 2_455 0.896(9) 2.215(10) 3.1000(17) 169.3(18)
O1 H1 N1 . 0.82 1.85 2.5720(15) 146.4