#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/26/8102697.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102697
loop_
_publ_author_name
'Heng-Yu Qian'
'Zhen-Xin Zhao'
'Chun-Xia Zhan'
'Zhi-Gang Yin'
_publ_section_title
;
 Crystal structure of
 N'-(3-ethoxy-4-hydroxybenzylidene)isonicotinohydrazide --- methanol
 (1:1), C15H15N3O3 · CH3OH
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              383
_journal_volume                  225
_journal_year                    2010
_chemical_formula_structural     'C16 H19 N3 O4'
_chemical_formula_sum            'C16 H19 N3 O4'
_chemical_formula_weight         317.34
_chemical_name_systematic
;
N'-(3-ethoxy-4-hydroxybenzylidene)isonicotinohydrazide methanol solvate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 109.068(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.2785(8)
_cell_length_b                   6.4429(3)
_cell_length_c                   11.8901(8)
_cell_measurement_reflns_used    1063
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2964
_cell_measurement_theta_min      3.0272
_cell_volume                     816.60(10)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'ω scans'
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0956
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3209
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.761
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.761
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0217P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0643
_reflns_number_gt                1481
_reflns_number_total             2617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2966.cff
_cod_data_source_block           m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        816.60(9)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               8102697
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7 C 0.5042(2) 0.2431(4) 0.3514(2) 0.0311(7) Uani 1 1 d . . .
H7A H 0.4823 0.3804 0.3586 0.037 Uiso 1 1 calc R . .
N1 N 0.4468(2) 0.1439(3) 0.25569(19) 0.0337(6) Uani 1 1 d . . .
C6 C 0.6032(2) 0.1471(4) 0.4495(2) 0.0274(7) Uani 1 1 d . . .
C8 C 0.2759(2) 0.1672(5) 0.0783(2) 0.0352(8) Uani 1 1 d . . .
C2 C 0.7386(2) 0.1645(4) 0.6522(2) 0.0316(7) Uani 1 1 d . . .
H2A H 0.7657 0.2342 0.7247 0.038 Uiso 1 1 calc R . .
N2 N 0.3598(2) 0.2631(3) 0.16964(18) 0.0338(7) Uani 1 1 d . . .
H2B H 0.3602 0.3962 0.1753 0.041 Uiso 1 1 calc R . .
C4 C 0.7503(3) -0.1270(4) 0.5317(2) 0.0282(7) Uani 1 1 d . . .
O1 O 0.8844(2) -0.0981(3) 0.73601(17) 0.0431(7) Uani 1 1 d . . .
C13 C 0.1648(3) 0.5093(4) 0.0070(2) 0.0405(9) Uani 1 1 d . . .
H13A H 0.2057 0.5714 0.0800 0.049 Uiso 1 1 calc R . .
C5 C 0.6563(2) -0.0436(4) 0.4374(2) 0.0286(7) Uani 1 1 d . . .
H5A H 0.6281 -0.1145 0.3654 0.034 Uiso 1 1 calc R . .
N3 N 0.0211(2) 0.5474(4) -0.1904(2) 0.0415(7) Uani 1 1 d . . .
C9 C 0.1888(3) 0.3058(4) -0.0128(2) 0.0295(7) Uani 1 1 d . . .
C14 C 0.7958(3) -0.4002(4) 0.4156(2) 0.0399(8) Uani 1 1 d . . .
H14A H 0.8119 -0.2974 0.3627 0.048 Uiso 1 1 calc R . .
H14B H 0.7105 -0.4501 0.3804 0.048 Uiso 1 1 calc R . .
O2 O 0.81188(17) -0.3097(3) 0.52955(15) 0.0357(5) Uani 1 1 d . . .
C1 C 0.6455(2) 0.2505(4) 0.5575(2) 0.0304(7) Uani 1 1 d . . .
H1C H 0.6112 0.3783 0.5661 0.037 Uiso 1 1 calc R . .
O3 O 0.2696(2) -0.0212(3) 0.06840(16) 0.0623(8) Uani 1 1 d . . .
C3 C 0.7914(2) -0.0224(4) 0.6408(2) 0.0280(7) Uani 1 1 d . . .
C11 C 0.0452(3) 0.3523(5) -0.2097(3) 0.0450(9) Uani 1 1 d . . .
H11A H 0.0052 0.2964 -0.2847 0.054 Uiso 1 1 calc R . .
C10 C 0.1270(3) 0.2256(4) -0.1242(2) 0.0394(8) Uani 1 1 d . . .
H10A H 0.1399 0.0886 -0.1420 0.047 Uiso 1 1 calc R . .
C12 C 0.0796(3) 0.6202(4) -0.0820(3) 0.0429(9) Uani 1 1 d . . .
H12A H 0.0619 0.7554 -0.0652 0.052 Uiso 1 1 calc R . .
C15 C 0.8868(3) -0.5775(4) 0.4329(3) 0.0523(10) Uani 1 1 d . . .
H15A H 0.8771 -0.6414 0.3574 0.078 Uiso 1 1 calc R . .
H15B H 0.8705 -0.6779 0.4856 0.078 Uiso 1 1 calc R . .
H15C H 0.9710 -0.5263 0.4666 0.078 Uiso 1 1 calc R . .
O4 O 0.4582(2) 0.6766(3) 0.18378(19) 0.0499(6) Uani 1 1 d . . .
H4 H 0.4110 0.7768 0.1730 0.075 Uiso 1 1 calc R . .
C16 C 0.5261(4) 0.6863(7) 0.1060(3) 0.0846(12) Uani 1 1 d . . .
H16A H 0.5814 0.8039 0.1254 0.127 Uiso 1 1 calc R . .
H16B H 0.4696 0.7001 0.0261 0.127 Uiso 1 1 calc R . .
H16C H 0.5745 0.5616 0.1125 0.127 Uiso 1 1 calc R . .
H1B H 0.902(3) -0.213(4) 0.727(2) 0.028(10) Uiso 1 1 d . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C7 C6 122.0(2) . . ?
N1 C7 H7A 119.0 . . ?
C6 C7 H7A 119.0 . . ?
C7 N1 N2 114.0(2) . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 118.6(3) . . ?
C5 C6 C7 122.1(2) . . ?
O3 C8 N2 122.8(2) . . ?
O3 C8 C9 121.4(2) . . ?
N2 C8 C9 115.8(2) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C8 N2 N1 118.9(2) . . ?
C8 N2 H2B 120.6 . . ?
N1 N2 H2B 120.6 . . ?
O2 C4 C5 125.5(2) . . ?
O2 C4 C3 114.5(2) . . ?
C5 C4 C3 120.0(2) . . ?
C3 O1 H1B 113(2) . . ?
C12 C13 C9 119.4(3) . . ?
C12 C13 H13A 120.3 . . ?
C9 C13 H13A 120.3 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C11 N3 C12 116.1(2) . . ?
C13 C9 C10 117.1(2) . . ?
C13 C9 C8 124.4(2) . . ?
C10 C9 C8 118.5(2) . . ?
O2 C14 C15 108.1(2) . . ?
O2 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O2 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C4 O2 C14 117.33(19) . . ?
C2 C1 C6 120.2(2) . . ?
C2 C1 H1C 119.9 . . ?
C6 C1 H1C 119.9 . . ?
O1 C3 C2 118.4(2) . . ?
O1 C3 C4 122.1(2) . . ?
C2 C3 C4 119.5(2) . . ?
N3 C11 C10 123.8(3) . . ?
N3 C11 H11A 118.1 . . ?
C10 C11 H11A 118.1 . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
N3 C12 C13 124.4(3) . . ?
N3 C12 H12A 117.8 . . ?
C13 C12 H12A 117.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 O4 H4 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 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
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C7 N1 1.281(3) . ?
C7 C6 1.463(3) . ?
C7 H7A 0.9300 . ?
N1 N2 1.394(2) . ?
C6 C1 1.385(3) . ?
C6 C5 1.395(3) . ?
C8 O3 1.219(3) . ?
C8 N2 1.337(3) . ?
C8 C9 1.497(4) . ?
C2 C3 1.370(3) . ?
C2 C1 1.380(3) . ?
C2 H2A 0.9300 . ?
N2 H2B 0.8600 . ?
C4 O2 1.371(3) . ?
C4 C5 1.377(3) . ?
C4 C3 1.399(3) . ?
O1 C3 1.358(3) . ?
O1 H1B 0.78(2) . ?
C13 C12 1.374(3) . ?
C13 C9 1.375(3) . ?
C13 H13A 0.9300 . ?
C5 H5A 0.9300 . ?
N3 C11 1.322(3) . ?
N3 C12 1.326(3) . ?
C9 C10 1.380(3) . ?
C14 O2 1.431(3) . ?
C14 C15 1.504(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 H1C 0.9300 . ?
C11 C10 1.392(4) . ?
C11 H11A 0.9300 . ?
C10 H10A 0.9300 . ?
C12 H12A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O4 C16 1.381(3) . ?
O4 H4 0.8200 . ?
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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B O4 0.86 2.103 2.869 148.12 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653985
