#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/02/2230276.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_2230276
loop_
_publ_author_name
'Zhang, Zhao-Po'
'Wang, Yuan'
'Lu, Ming-Jia'
'Jia, Lei-Wei'
'Qiao, Hong-Chang'
_publ_section_title
;
 Ethyl
 5-{[(E)-2-(isonicotinoyl)hydrazinylidene]methyl}-3,4-dimethyl-1H-pyrrole-2-carboxylate
 dihydrate
;
_journal_coeditor_code           CV5084
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1413
_journal_paper_doi               10.1107/S1600536811017132
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H18 N4 O3, 2H2 O'
_chemical_formula_moiety         'C16 H18 N4 O3, 2(H2 O)'
_chemical_formula_sum            'C16 H22 N4 O5'
_chemical_formula_weight         350.38
_chemical_name_systematic
;
Ethyl 5-{[(E)-2-(isonicotinoyl)hydrazinylidene]methyl}-
3,4-dimethyl-1H-pyrrole-2-carboxylate dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.814(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.297(4)
_cell_length_b                   18.120(6)
_cell_length_c                   11.834(4)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.70
_cell_volume                     1778.3(12)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and 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  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10998
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0.069
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.02P)²+3.5P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1630
_refine_ls_wR_factor_ref         0.1759
_reflns_number_gt                2671
_reflns_number_total             3839
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cv5084.cif
_cod_data_source_block           I
_cod_original_cell_volume        1778.3(11)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               2230276
_cod_database_fobs_code          2230276
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'
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 0.6319(3) 0.46189(12) 0.4160(2) 0.0530(6) Uani d . 1 . .
O O2 1.1091(4) 0.29040(14) 0.9756(2) 0.0660(8) Uani d . 1 . .
O O3 0.9696(3) 0.27423(12) 0.8122(2) 0.0564(7) Uani d . 1 . .
N N1 0.4775(4) 0.68078(16) 0.1780(2) 0.0532(8) Uani d . 1 . .
N N2 0.7766(3) 0.55247(14) 0.5019(2) 0.0406(6) Uani d . 1 . .
H H2A 0.8043 0.5982 0.5024 0.049 Uiso calc R 1 . .
N N3 0.8374(3) 0.50452(14) 0.5828(2) 0.0420(6) Uani d . 1 . .
N N4 0.9761(3) 0.41573(14) 0.7584(2) 0.0415(6) Uani d . 1 . .
H H4A 0.9158 0.3892 0.7141 0.050 Uiso calc R 1 . .
C C1 0.4299(4) 0.6106(2) 0.1836(3) 0.0545(9) Uani d . 1 . .
H H1 0.3507 0.5946 0.1319 0.065 Uiso calc R 1 . .
C C2 0.4901(4) 0.56074(19) 0.2606(3) 0.0498(8) Uani d . 1 . .
H H2 0.4522 0.5124 0.2604 0.060 Uiso calc R 1 . .
C C3 0.6076(4) 0.58255(17) 0.3388(3) 0.0385(7) Uani d . 1 . .
C C4 0.6579(5) 0.65506(18) 0.3348(3) 0.0531(9) Uani d . 1 . .
H H4 0.7355 0.6730 0.3861 0.064 Uiso calc R 1 . .
C C5 0.5898(5) 0.70012(19) 0.2527(3) 0.0605(10) Uani d . 1 . .
H H5 0.6267 0.7485 0.2500 0.073 Uiso calc R 1 . .
C C6 0.6727(4) 0.52615(16) 0.4219(3) 0.0380(7) Uani d . 1 . .
C C7 0.9388(4) 0.53192(17) 0.6540(3) 0.0418(7) Uani d . 1 . .
H H7A 0.9686 0.5811 0.6471 0.050 Uiso calc R 1 . .
C C8 1.0084(4) 0.48875(17) 0.7448(3) 0.0412(7) Uani d . 1 . .
C C9 1.1112(4) 0.51125(18) 0.8322(3) 0.0428(8) Uani d . 1 . .
C C10 1.1406(4) 0.44984(18) 0.9021(3) 0.0423(7) Uani d . 1 . .
C C11 1.0555(4) 0.39167(17) 0.8543(3) 0.0411(7) Uani d . 1 . .
C C12 1.1778(5) 0.5870(2) 0.8501(3) 0.0654(11) Uani d . 1 . .
H H12A 1.1754 0.6131 0.7795 0.098 Uiso calc R 1 . .
H H12B 1.2870 0.5837 0.8789 0.098 Uiso calc R 1 . .
H H12C 1.1137 0.6129 0.9033 0.098 Uiso calc R 1 . .
C C13 1.2480(5) 0.4481(2) 1.0061(3) 0.0589(10) Uani d . 1 . .
H H13A 1.1894 0.4654 1.0695 0.088 Uiso calc R 1 . .
H H13B 1.3398 0.4792 0.9954 0.088 Uiso calc R 1 . .
H H13C 1.2835 0.3984 1.0201 0.088 Uiso calc R 1 . .
C C14 1.0502(4) 0.31492(18) 0.8893(3) 0.0452(8) Uani d . 1 . .
C C15 0.9548(5) 0.19650(18) 0.8342(3) 0.0609(10) Uani d . 1 . .
H H15A 0.8978 0.1883 0.9034 0.073 Uiso calc R 1 . .
H H15B 1.0605 0.1738 0.8420 0.073 Uiso calc R 1 . .
C C16 0.8642(7) 0.1652(2) 0.7371(4) 0.0830(15) Uani d . 1 . .
H H16A 0.7623 0.1900 0.7281 0.125 Uiso calc R 1 . .
H H16B 0.8461 0.1135 0.7498 0.125 Uiso calc R 1 . .
H H16C 0.9247 0.1715 0.6700 0.125 Uiso calc R 1 . .
O O1W 0.4291(4) 0.80318(15) 0.0290(3) 0.0654(8) Uani d . 1 . .
H H1C 0.428(7) 0.770(3) 0.059(5) 0.098 Uiso d . 1 . .
H H1D 0.528(6) 0.813(3) 0.001(4) 0.098 Uiso d . 1 . .
O O2W 0.7783(3) 0.34071(15) 0.5656(2) 0.0588(7) Uani d . 1 . .
H H2C 0.704(6) 0.305(3) 0.544(4) 0.088 Uiso d . 1 . .
H H2D 0.744(6) 0.380(3) 0.541(4) 0.088 Uiso 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
C14 O3 C15 . . 117.4(3) ?
C5 N1 C1 . . 115.2(3) ?
C6 N2 N3 . . 118.5(3) ?
C6 N2 H2A . . 120.7 ?
N3 N2 H2A . . 120.7 ?
C7 N3 N2 . . 115.7(3) ?
C8 N4 C11 . . 108.5(3) ?
C8 N4 H4A . . 125.8 ?
C11 N4 H4A . . 125.8 ?
N1 C1 C2 . . 124.1(3) ?
N1 C1 H1 . . 117.9 ?
C2 C1 H1 . . 117.9 ?
C1 C2 C3 . . 119.6(3) ?
C1 C2 H2 . . 120.2 ?
C3 C2 H2 . . 120.2 ?
C4 C3 C2 . . 117.2(3) ?
C4 C3 C6 . . 124.5(3) ?
C2 C3 C6 . . 118.3(3) ?
C3 C4 C5 . . 118.1(3) ?
C3 C4 H4 . . 120.9 ?
C5 C4 H4 . . 120.9 ?
N1 C5 C4 . . 125.7(3) ?
N1 C5 H5 . . 117.1 ?
C4 C5 H5 . . 117.1 ?
O1 C6 N2 . . 123.4(3) ?
O1 C6 C3 . . 121.3(3) ?
N2 C6 C3 . . 115.3(3) ?
N3 C7 C8 . . 121.7(3) ?
N3 C7 H7A . . 119.2 ?
C8 C7 H7A . . 119.2 ?
N4 C8 C9 . . 108.5(3) ?
N4 C8 C7 . . 122.9(3) ?
C9 C8 C7 . . 128.6(3) ?
C8 C9 C10 . . 107.4(3) ?
C8 C9 C12 . . 126.5(3) ?
C10 C9 C12 . . 126.1(3) ?
C11 C10 C9 . . 106.7(3) ?
C11 C10 C13 . . 127.2(3) ?
C9 C10 C13 . . 126.1(3) ?
N4 C11 C10 . . 108.9(3) ?
N4 C11 C14 . . 121.6(3) ?
C10 C11 C14 . . 129.4(3) ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O2 C14 O3 . . 123.9(3) ?
O2 C14 C11 . . 125.5(3) ?
O3 C14 C11 . . 110.7(3) ?
O3 C15 C16 . . 106.3(3) ?
O3 C15 H15A . . 110.5 ?
C16 C15 H15A . . 110.5 ?
O3 C15 H15B . . 110.5 ?
C16 C15 H15B . . 110.5 ?
H15A C15 H15B . . 108.7 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
H1C O1W H1D . . 112(5) ?
H2C O2W H2D . . 107(4) ?
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 C6 . 1.214(4) ?
O2 C14 . 1.204(4) ?
O3 C14 . 1.336(4) ?
O3 C15 . 1.438(4) ?
N1 C5 . 1.312(5) ?
N1 C1 . 1.334(5) ?
N2 C6 . 1.347(4) ?
N2 N3 . 1.377(3) ?
N2 H2A . 0.8600 ?
N3 C7 . 1.273(4) ?
N4 C8 . 1.361(4) ?
N4 C11 . 1.366(4) ?
N4 H4A . 0.8600 ?
C1 C2 . 1.366(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.380(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.380(4) ?
C3 C6 . 1.506(4) ?
C4 C5 . 1.376(5) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C7 C8 . 1.435(4) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.382(5) ?
C9 C10 . 1.403(4) ?
C9 C12 . 1.492(5) ?
C10 C11 . 1.380(4) ?
C10 C13 . 1.497(5) ?
C11 C14 . 1.452(4) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C15 C16 . 1.468(5) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
O1W H1C . 0.69(5) ?
O1W H1D . 0.91(5) ?
O2W H2C . 0.92(5) ?
O2W H2D . 0.82(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 H2A O1W 4_676 0.86 2.08 2.919(4) 164
N4 H4A O2W . 0.86 2.24 3.084(4) 165
O1W H1C N1 . 0.69(5) 2.18(5) 2.854(4) 164(6)
O1W H1D O2W 2_655 0.91(5) 1.88(5) 2.790(5) 174(5)
O2W H2C O2 4_565 0.92(5) 2.06(5) 2.941(4) 160(4)
O2W H2D O1 . 0.82(5) 2.27(5) 3.048(4) 159(5)
O2W H2D N3 . 0.82(5) 2.43(5) 3.014(4) 129(4)
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
C6 N2 N3 C7 . . . . 177.9(3) ?
C5 N1 C1 C2 . . . . 0.3(6) ?
N1 C1 C2 C3 . . . . 0.1(6) ?
C1 C2 C3 C4 . . . . 0.3(5) ?
C1 C2 C3 C6 . . . . -179.4(3) ?
C2 C3 C4 C5 . . . . -1.0(5) ?
C6 C3 C4 C5 . . . . 178.7(3) ?
C1 N1 C5 C4 . . . . -1.1(6) ?
C3 C4 C5 N1 . . . . 1.5(7) ?
N3 N2 C6 O1 . . . . -1.4(5) ?
N3 N2 C6 C3 . . . . 178.1(3) ?
C4 C3 C6 O1 . . . . -174.7(3) ?
C2 C3 C6 O1 . . . . 5.0(5) ?
C4 C3 C6 N2 . . . . 5.8(5) ?
C2 C3 C6 N2 . . . . -174.5(3) ?
N2 N3 C7 C8 . . . . 178.2(3) ?
C11 N4 C8 C9 . . . . 0.8(4) ?
C11 N4 C8 C7 . . . . -177.7(3) ?
N3 C7 C8 N4 . . . . 2.6(5) ?
N3 C7 C8 C9 . . . . -175.5(3) ?
N4 C8 C9 C10 . . . . -0.8(4) ?
C7 C8 C9 C10 . . . . 177.6(3) ?
N4 C8 C9 C12 . . . . 179.8(3) ?
C7 C8 C9 C12 . . . . -1.8(6) ?
C8 C9 C10 C11 . . . . 0.4(4) ?
C12 C9 C10 C11 . . . . 179.9(3) ?
C8 C9 C10 C13 . . . . 178.8(3) ?
C12 C9 C10 C13 . . . . -1.8(6) ?
C8 N4 C11 C10 . . . . -0.5(4) ?
C8 N4 C11 C14 . . . . -177.4(3) ?
C9 C10 C11 N4 . . . . 0.0(4) ?
C13 C10 C11 N4 . . . . -178.3(3) ?
C9 C10 C11 C14 . . . . 176.6(3) ?
C13 C10 C11 C14 . . . . -1.7(6) ?
C15 O3 C14 O2 . . . . -0.7(5) ?
C15 O3 C14 C11 . . . . 179.5(3) ?
N4 C11 C14 O2 . . . . -175.6(3) ?
C10 C11 C14 O2 . . . . 8.2(6) ?
N4 C11 C14 O3 . . . . 4.3(5) ?
C10 C11 C14 O3 . . . . -172.0(3) ?
C14 O3 C15 C16 . . . . -179.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656690
