##############################################################################
### ###
### Electronic paper (Acta Crystallographica Section E) ###
### ###
##############################################################################
# #
# 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 2008-07-28
_journal_date_accepted 2008-07-31
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2008
_journal_volume 64
_journal_issue 9
_journal_page_first o1695
_journal_page_last o1695
_journal_paper_category QO
_journal_coeditor_code CI2648
_publ_contact_author_name 'Jiufu Lu'
_publ_contact_author_address
;
School of Chemistry and Environmental Science
Shaanxi University of Technology
Hanzhong 723000
People's Republic of China
;
_publ_contact_author_email jiufulu@163.com
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_section_title
;
2-Methoxy-N'-(2-methoxybenzylidene)benzohydrazide
;
loop_
_publ_author_name
_publ_author_address
'Jiu-Fu Lu'
;
School of Chemistry and Environmental Science
Shaanxi University of Technology
Hanzhong 723000
People's Republic of China
;
'Suo-Tian Min'
;
School of Chemistry and Environmental Science
Shaanxi University of Technology
Hanzhong 723000
People's Republic of China
;
'Xiao-Hui Ji'
;
School of Chemistry and Environmental Science
Shaanxi University of Technology
Hanzhong 723000
People's Republic of China
;
'Zhong-Hai Dang'
;
School of Chemistry and Environmental Science
Shaanxi University of Technology
Hanzhong 723000
People's Republic of China
;
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
2-Methoxy-N'-(2-methoxybenzylidene)benzohydrazide
;
_chemical_name_common ?
_chemical_formula_moiety 'C16 H16 N2 O3'
_chemical_formula_sum 'C16 H16 N2 O3'
_chemical_formula_iupac 'C16 H16 N2 O3'
_chemical_formula_weight 284.31
_chemical_melting_point ?
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 21'
_symmetry_space_group_name_Hall 'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 4.9998(13)
_cell_length_b 13.475(4)
_cell_length_c 10.824(3)
_cell_angle_alpha 90.00
_cell_angle_beta 93.674(4)
_cell_angle_gamma 90.00
_cell_volume 727.7(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 744
_cell_measurement_theta_min 2.5
_cell_measurement_theta_max 24.0
_cell_measurement_temperature 298(2)
_exptl_crystal_description Block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.28
_exptl_crystal_density_diffrn 1.297
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 300
_exptl_absorpt_coefficient_mu 0.091
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min 0.9732
_exptl_absorpt_correction_T_max 0.9750
_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 APEXII CCD area-detector'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 6081
_diffrn_reflns_av_R_equivalents 0.0546
_diffrn_reflns_av_sigmaI/netI 0.0601
_diffrn_reflns_theta_min 1.89
_diffrn_reflns_theta_max 27.00
_diffrn_reflns_theta_full 27.00
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_standards_number 0
_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^ > 2sigma(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 1647
_reflns_number_gt 1229
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0762
_refine_ls_R_factor_gt 0.0501
_refine_ls_wR_factor_gt 0.0864
_refine_ls_wR_factor_ref 0.0945
_refine_ls_goodness_of_fit_ref 1.114
_refine_ls_restrained_S_all 1.113
_refine_ls_number_reflns 1647
_refine_ls_number_parameters 195
_refine_ls_number_restraints 2
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0297P)^2^] 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 0.001
_refine_ls_shift/su_max_lt 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.155
_refine_diff_density_min -0.144
_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 'APEX2 (Bruker, 2004)'
_computing_cell_refinement 'SAINT (Bruker, 2004)'
_computing_data_reduction 'SAINT (Bruker, 2004)'
_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
O O1 0.4130(5) 0.5063(2) 1.0258(2) 0.0579(8) Uani d . 1 . .
O O2 1.2673(4) 0.71624(19) 0.6930(2) 0.0436(6) Uani d . 1 . .
O O3 0.6361(5) 0.7245(2) 0.4683(2) 0.0513(6) Uani d . 1 . .
N N1 0.8931(5) 0.5916(2) 0.7771(2) 0.0357(7) Uani d . 1 . .
N N2 0.8339(5) 0.67811(19) 0.7116(3) 0.0354(7) Uani d D 1 . .
C C1 0.7337(7) 0.4561(2) 0.8904(3) 0.0371(9) Uani d . 1 . .
C C2 0.5766(7) 0.4321(3) 0.9892(3) 0.0426(9) Uani d . 1 . .
C C3 0.6008(7) 0.3398(3) 1.0439(3) 0.0501(10) Uani d . 1 . .
H H3 0.4953 0.3233 1.1086 0.060 Uiso calc R 1 . .
C C4 0.7794(8) 0.2725(3) 1.0032(4) 0.0549(11) Uani d . 1 . .
H H4 0.7928 0.2102 1.0400 0.066 Uiso calc R 1 . .
C C5 0.9407(8) 0.2954(3) 0.9081(4) 0.0537(10) Uani d . 1 . .
H H5 1.0645 0.2498 0.8818 0.064 Uiso calc R 1 . .
C C6 0.9142(7) 0.3876(3) 0.8529(3) 0.0455(9) Uani d . 1 . .
H H6 1.0216 0.4036 0.7887 0.055 Uiso calc R 1 . .
C C7 0.6996(7) 0.5520(2) 0.8295(3) 0.0377(8) Uani d . 1 . .
H H7 0.5353 0.5844 0.8291 0.045 Uiso calc R 1 . .
C C8 1.0305(6) 0.7328(2) 0.6674(3) 0.0296(7) Uani d . 1 . .
C C9 0.9390(6) 0.8198(2) 0.5913(3) 0.0343(8) Uani d . 1 . .
C C10 0.7391(6) 0.8162(3) 0.4959(3) 0.0358(8) Uani d . 1 . .
C C11 0.6635(7) 0.9012(3) 0.4321(3) 0.0518(10) Uani d . 1 . .
H H11 0.5257 0.8990 0.3703 0.062 Uiso calc R 1 . .
C C12 0.7913(8) 0.9890(3) 0.4597(4) 0.0606(12) Uani d . 1 . .
H H12 0.7384 1.0462 0.4168 0.073 Uiso calc R 1 . .
C C13 0.9946(8) 0.9936(3) 0.5493(4) 0.0617(12) Uani d . 1 . .
H H13 1.0835 1.0533 0.5659 0.074 Uiso calc R 1 . .
C C14 1.0677(7) 0.9096(3) 0.6151(4) 0.0478(10) Uani d . 1 . .
H H14 1.2059 0.9131 0.6767 0.057 Uiso calc R 1 . .
C C15 0.2563(8) 0.4878(4) 1.1267(4) 0.0653(12) Uani d . 1 . .
H H15A 0.1495 0.4295 1.1105 0.098 Uiso calc R 1 . .
H H15B 0.1410 0.5435 1.1385 0.098 Uiso calc R 1 . .
H H15C 0.3714 0.4778 1.2001 0.098 Uiso calc R 1 . .
C C16 0.4372(8) 0.7167(4) 0.3692(3) 0.0712(12) Uani d . 1 . .
H H16A 0.2821 0.7542 0.3885 0.107 Uiso calc R 1 . .
H H16B 0.3884 0.6483 0.3573 0.107 Uiso calc R 1 . .
H H16C 0.5066 0.7422 0.2949 0.107 Uiso calc R 1 . .
H H2 0.662(3) 0.696(3) 0.696(3) 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
O1 0.0577(16) 0.0581(19) 0.0601(19) 0.0064(15) 0.0196(15) 0.0132(15)
O2 0.0265(12) 0.0451(14) 0.0586(14) 0.0050(12) -0.0024(10) 0.0062(13)
O3 0.0604(15) 0.0471(15) 0.0439(13) -0.0052(14) -0.0149(11) 0.0053(14)
N1 0.0391(16) 0.0318(15) 0.0356(15) 0.0028(13) -0.0030(13) 0.0079(13)
N2 0.0271(14) 0.0357(16) 0.0428(16) 0.0036(13) -0.0018(13) 0.0124(13)
C1 0.037(2) 0.038(2) 0.0354(19) -0.0036(16) -0.0070(16) 0.0053(16)
C2 0.041(2) 0.046(2) 0.040(2) -0.0060(18) -0.0050(18) 0.0062(18)
C3 0.054(2) 0.051(3) 0.045(2) -0.011(2) -0.0020(18) 0.0176(19)
C4 0.069(3) 0.035(2) 0.058(3) 0.000(2) -0.016(2) 0.018(2)
C5 0.061(3) 0.043(2) 0.056(3) 0.0023(19) -0.001(2) 0.001(2)
C6 0.049(2) 0.042(2) 0.045(2) -0.0021(19) 0.0002(18) 0.0085(18)
C7 0.0336(18) 0.043(2) 0.0357(19) 0.0002(16) -0.0008(16) 0.0078(16)
C8 0.0279(17) 0.0279(18) 0.0332(16) -0.0013(15) 0.0026(13) -0.0029(15)
C9 0.0317(17) 0.0346(19) 0.0377(18) 0.0046(15) 0.0098(14) 0.0017(16)
C10 0.0368(19) 0.0353(19) 0.0357(19) 0.0037(16) 0.0051(15) 0.0015(17)
C11 0.055(2) 0.056(3) 0.044(2) 0.008(2) 0.001(2) 0.013(2)
C12 0.065(3) 0.046(3) 0.071(3) 0.007(2) 0.009(2) 0.027(2)
C13 0.072(3) 0.039(2) 0.076(3) -0.010(2) 0.014(3) 0.008(2)
C14 0.048(2) 0.037(2) 0.058(2) -0.0087(19) 0.0060(19) 0.003(2)
C15 0.060(3) 0.083(3) 0.054(3) -0.002(3) 0.012(2) 0.009(2)
C16 0.077(3) 0.078(3) 0.055(2) -0.014(3) -0.023(2) 0.009(3)
_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
O1 C2 . 1.367(4) ?
O1 C15 . 1.407(4) ?
O2 C8 . 1.220(3) ?
O3 C10 . 1.364(4) ?
O3 C16 . 1.419(4) ?
N1 C7 . 1.270(4) ?
N1 N2 . 1.387(3) ?
N2 C8 . 1.341(4) ?
N2 H2 . 0.901(10) ?
C1 C6 . 1.370(5) ?
C1 C2 . 1.405(5) ?
C1 C7 . 1.456(4) ?
C2 C3 . 1.380(5) ?
C3 C4 . 1.365(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.383(5) ?
C4 H4 . 0.93 ?
C5 C6 . 1.381(5) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 H7 . 0.93 ?
C8 C9 . 1.488(4) ?
C9 C14 . 1.387(5) ?
C9 C10 . 1.391(4) ?
C10 C11 . 1.378(5) ?
C11 C12 . 1.368(5) ?
C11 H11 . 0.93 ?
C12 C13 . 1.360(5) ?
C12 H12 . 0.93 ?
C13 C14 . 1.375(5) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
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 O1 C15 . . 118.0(3) ?
C10 O3 C16 . . 118.0(3) ?
C7 N1 N2 . . 115.9(3) ?
C8 N2 N1 . . 120.5(2) ?
C8 N2 H2 . . 120(3) ?
N1 N2 H2 . . 120(3) ?
C6 C1 C2 . . 118.8(3) ?
C6 C1 C7 . . 121.6(3) ?
C2 C1 C7 . . 119.6(3) ?
O1 C2 C3 . . 125.0(3) ?
O1 C2 C1 . . 115.3(3) ?
C3 C2 C1 . . 119.7(4) ?
C4 C3 C2 . . 120.1(4) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 121.1(3) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C6 C5 C4 . . 118.6(4) ?
C6 C5 H5 . . 120.7 ?
C4 C5 H5 . . 120.7 ?
C1 C6 C5 . . 121.6(4) ?
C1 C6 H6 . . 119.2 ?
C5 C6 H6 . . 119.2 ?
N1 C7 C1 . . 120.3(3) ?
N1 C7 H7 . . 119.9 ?
C1 C7 H7 . . 119.9 ?
O2 C8 N2 . . 122.8(3) ?
O2 C8 C9 . . 122.0(3) ?
N2 C8 C9 . . 115.1(3) ?
C14 C9 C10 . . 118.1(3) ?
C14 C9 C8 . . 117.5(3) ?
C10 C9 C8 . . 124.3(3) ?
O3 C10 C11 . . 123.8(3) ?
O3 C10 C9 . . 115.9(3) ?
C11 C10 C9 . . 120.3(3) ?
C12 C11 C10 . . 120.0(4) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C13 C12 C11 . . 120.8(4) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C14 . . 119.6(4) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C13 C14 C9 . . 121.2(4) ?
C13 C14 H14 . . 119.4 ?
C9 C14 H14 . . 119.4 ?
O1 C15 H15A . . 109.5 ?
O1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O3 C16 H16A . . 109.5 ?
O3 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O3 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 O2 1_455 0.900(10)
1.990(10)
2.873(3) 167(4)