#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225604.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_2225604
loop_
_publ_author_name
'Tang, Sheng-Jiao'
'Li, Hai-Ping'
'Lin, Xin-Yong'
'Wu, Wen-Shi'
_publ_section_title
;
 4-Ethoxy-N'-propanoylpyridine-2-carbohydrazide
;
_journal_coeditor_code           JH2133
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o920
_journal_paper_doi               10.1107/S1600536810010135
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H15 N3 O3'
_chemical_formula_moiety         'C11 H15 N3 O3'
_chemical_formula_sum            'C11 H15 N3 O3'
_chemical_formula_weight         237.26
_chemical_melting_point_gt       407
_chemical_melting_point_lt       407.5
_chemical_name_systematic
;
4-Ethoxy-N'-propanoylpyridine-2-carbohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.534(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.377(5)
_cell_length_b                   4.745(2)
_cell_length_c                   23.244(10)
_cell_measurement_reflns_used    2827
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.74
_cell_volume                     1237.5(9)
_computing_cell_refinement       'XSCANS (Bruker, 1999)'
_computing_data_collection       'XSCANS (Bruker, 1999)'
_computing_data_reduction        'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9032
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0530
_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)+(0.0800P)²+0.3962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1498
_reflns_number_gt                2297
_reflns_number_total             2803
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2133.cif
_cod_data_source_block           I
_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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1237.3(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225604
_cod_database_fobs_code          2225604
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C C1 0.16780(13) 0.4979(3) 0.41169(7) 0.0451(4) Uani d . 1 . .
C C2 0.18448(13) 0.3174(3) 0.45907(7) 0.0476(4) Uani d . 1 . .
H H2 0.1211 0.2618 0.4771 0.057 Uiso calc R 1 . .
C C3 0.29993(13) 0.2221(4) 0.47874(6) 0.0467(4) Uani d . 1 . .
C C4 0.39038(13) 0.3146(4) 0.45039(7) 0.0552(4) Uani d . 1 . .
H H4 0.4682 0.2531 0.4622 0.066 Uiso calc R 1 . .
C C5 0.36375(14) 0.4981(4) 0.40462(8) 0.0608(5) Uani d . 1 . .
H H5 0.4260 0.5619 0.3867 0.073 Uiso calc R 1 . .
C C6 0.04284(13) 0.5972(4) 0.38881(7) 0.0493(4) Uani d . 1 . .
C C7 -0.15075(13) 0.6370(3) 0.27838(7) 0.0446(4) Uani d . 1 . .
C C8 -0.26718(18) 0.7610(4) 0.24930(10) 0.0732(6) Uani d . 1 . .
H H8A -0.2938 0.8948 0.2760 0.088 Uiso calc R 1 . .
H H8B -0.2530 0.8654 0.2152 0.088 Uiso calc R 1 . .
C C9 -0.36264(19) 0.5625(6) 0.23120(15) 0.1004(9) Uani d . 1 . .
H H9D -0.4327 0.6624 0.2134 0.151 Uiso calc R 1 . .
H H9A -0.3795 0.4607 0.2646 0.151 Uiso calc R 1 . .
H H9B -0.3391 0.4325 0.2036 0.151 Uiso calc R 1 . .
C C10 0.24191(15) -0.0530(4) 0.55627(8) 0.0557(4) Uani d . 1 . .
H H10A 0.1822 -0.1624 0.5311 0.067 Uiso calc R 1 . .
H H10B 0.2029 0.1047 0.5718 0.067 Uiso calc R 1 . .
C C11 0.30482(18) -0.2325(5) 0.60472(9) 0.0708(6) Uani d . 1 . .
H H11A 0.2481 -0.3041 0.6274 0.106 Uiso calc R 1 . .
H H11B 0.3636 -0.1216 0.6292 0.106 Uiso calc R 1 . .
H H11C 0.3431 -0.3871 0.5886 0.106 Uiso calc R 1 . .
N N1 0.25346(11) 0.5917(3) 0.38402(6) 0.0540(4) Uani d . 1 . .
N N2 0.03317(11) 0.7407(3) 0.33833(6) 0.0506(3) Uani d . 1 . .
H H2A 0.0960 0.7822 0.3240 0.061 Uiso calc R 1 . .
N N3 -0.07761(11) 0.8213(3) 0.30948(6) 0.0490(3) Uani d . 1 . .
H H3A -0.0999 0.9937 0.3116 0.059 Uiso calc R 1 . .
O O1 -0.04003(11) 0.5488(4) 0.41406(6) 0.0787(5) Uani d . 1 . .
O O2 -0.12542(11) 0.3873(2) 0.27472(6) 0.0604(4) Uani d . 1 . .
O O3 0.33191(10) 0.0459(3) 0.52425(5) 0.0598(4) Uani d . 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 125.26(14) ?
N1 C1 C6 . . 116.63(14) ?
C2 C1 C6 . . 118.10(14) ?
C1 C2 C3 . . 117.38(14) ?
C1 C2 H2 . . 121.3 ?
C3 C2 H2 . . 121.3 ?
O3 C3 C4 . . 116.42(13) ?
O3 C3 C2 . . 125.11(14) ?
C4 C3 C2 . . 118.46(15) ?
C5 C4 C3 . . 119.08(14) ?
C5 C4 H4 . . 120.5 ?
C3 C4 H4 . . 120.5 ?
N1 C5 C4 . . 124.12(16) ?
N1 C5 H5 . . 117.9 ?
C4 C5 H5 . . 117.9 ?
O1 C6 N2 . . 124.08(14) ?
O1 C6 C1 . . 122.24(15) ?
N2 C6 C1 . . 113.69(14) ?
O2 C7 N3 . . 122.59(14) ?
O2 C7 C8 . . 123.14(15) ?
N3 C7 C8 . . 114.25(13) ?
C9 C8 C7 . . 116.04(16) ?
C9 C8 H8A . . 108.3 ?
C7 C8 H8A . . 108.3 ?
C9 C8 H8B . . 108.3 ?
C7 C8 H8B . . 108.3 ?
H8A C8 H8B . . 107.4 ?
C8 C9 H9D . . 109.5 ?
C8 C9 H9A . . 109.5 ?
H9D C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9D C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O3 C10 C11 . . 106.39(14) ?
O3 C10 H10A . . 110.5 ?
C11 C10 H10A . . 110.5 ?
O3 C10 H10B . . 110.5 ?
C11 C10 H10B . . 110.5 ?
H10A C10 H10B . . 108.6 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C1 N1 C5 . . 115.67(15) ?
C6 N2 N3 . . 120.02(13) ?
C6 N2 H2A . . 120.0 ?
N3 N2 H2A . . 120.0 ?
C7 N3 N2 . . 121.25(12) ?
C7 N3 H3A . . 119.4 ?
N2 N3 H3A . . 119.4 ?
C3 O3 C10 . . 118.97(12) ?
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
C1 N1 . 1.330(2) ?
C1 C2 . 1.383(2) ?
C1 C6 . 1.508(2) ?
C2 C3 . 1.393(2) ?
C2 H2 . 0.9300 ?
C3 O3 . 1.3502(19) ?
C3 C4 . 1.382(2) ?
C4 C5 . 1.369(3) ?
C4 H4 . 0.9300 ?
C5 N1 . 1.342(2) ?
C5 H5 . 0.9300 ?
C6 O1 . 1.212(2) ?
C6 N2 . 1.345(2) ?
C7 O2 . 1.2256(19) ?
C7 N3 . 1.335(2) ?
C7 C8 . 1.504(2) ?
C8 C9 . 1.446(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9D . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C10 O3 . 1.440(2) ?
C10 C11 . 1.496(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
N2 N3 . 1.3800(17) ?
N2 H2A . 0.8600 ?
N3 H3A . 0.8600 ?
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
N2 H2A O2 2_555 0.86 2.43 3.067(2) 131.8 yes
N3 H3A O2 1_565 0.86 2.06 2.831(2) 149.6 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -1.2(3) ?
C6 C1 C2 C3 . . . . 178.43(14) ?
C1 C2 C3 O3 . . . . 179.96(15) ?
C1 C2 C3 C4 . . . . 0.6(2) ?
O3 C3 C4 C5 . . . . -178.73(17) ?
C2 C3 C4 C5 . . . . 0.7(3) ?
C3 C4 C5 N1 . . . . -1.6(3) ?
N1 C1 C6 O1 . . . . -172.29(17) ?
C2 C1 C6 O1 . . . . 8.0(3) ?
N1 C1 C6 N2 . . . . 8.0(2) ?
C2 C1 C6 N2 . . . . -171.66(14) ?
O2 C7 C8 C9 . . . . 17.9(3) ?
N3 C7 C8 C9 . . . . -161.1(2) ?
C2 C1 N1 C5 . . . . 0.4(3) ?
C6 C1 N1 C5 . . . . -179.20(15) ?
C4 C5 N1 C1 . . . . 1.0(3) ?
O1 C6 N2 N3 . . . . -5.8(3) ?
C1 C6 N2 N3 . . . . 173.92(13) ?
O2 C7 N3 N2 . . . . 1.7(2) ?
C8 C7 N3 N2 . . . . -179.35(16) ?
C6 N2 N3 C7 . . . . -77.1(2) ?
C4 C3 O3 C10 . . . . 178.74(16) ?
C2 C3 O3 C10 . . . . -0.7(3) ?
C11 C10 O3 C3 . . . . -177.84(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744718
