#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/43/2014398.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_2014398
loop_
_publ_author_name
'Wardell, Solange M. S. V.'
'de Souza, Marcus V. N.'
'Wardell, James L.'
'Low, John N.'
'Glidewell, Christopher'
_publ_section_title
;
 Pyrrole-2-carbaldehyde isonicotinoylhydrazone monohydrate redetermined
 at 120K
;
_journal_coeditor_code           SK1894
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o47
_journal_page_last               o49
_journal_paper_doi               10.1107/S0108270105040230
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H10 N4 O , H2 O'
_chemical_formula_moiety         'C11 H10 N4 O , H2 O'
_chemical_formula_sum            'C11 H12 N4 O2'
_chemical_formula_weight         232.25
_chemical_name_systematic
;
Pyrrole-2-carbaldehyde isonicotinoylhydrazone monohydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4224(3)
_cell_length_b                   7.2115(5)
_cell_length_c                   23.6073(16)
_cell_measurement_reflns_used    1237
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.95
_cell_volume                     1093.38(12)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR91 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5095
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.408
_refine_ls_extinction_coef       0.031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0372P)²+2.0901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                1157
_reflns_number_total             1279
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1894.cif
_cod_data_source_block           I
_cod_database_code               2014398
_cod_database_fobs_code          2014398
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_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
_atom_site_type_symbol
O1 0.6865(6) 0.2980(5) 0.66359(13) 0.0284(8) Uani d . 1 . . O
N11 0.1197(7) 0.3659(6) 0.80686(15) 0.0246(9) Uani d . 1 . . N
N17 0.4058(7) 0.2053(5) 0.61219(13) 0.0210(9) Uani d . 1 . . N
N21 0.7902(6) -0.0358(5) 0.49180(14) 0.0204(9) Uani d . 1 . . N
N27 0.5395(6) 0.1447(5) 0.56955(14) 0.0195(8) Uani d . 1 . . N
C12 0.0430(8) 0.3915(6) 0.75496(18) 0.0225(10) Uani d . 1 . . C
C13 0.1532(7) 0.3589(6) 0.70543(17) 0.0186(10) Uani d . 1 . . C
C14 0.3577(7) 0.3029(6) 0.70943(17) 0.0159(9) Uani d . 1 . . C
C15 0.4432(8) 0.2752(6) 0.76360(17) 0.0239(11) Uani d . 1 . . C
C16 0.3173(9) 0.3077(7) 0.81000(18) 0.0281(12) Uani d . 1 . . C
C17 0.4967(7) 0.2699(6) 0.65957(17) 0.0188(9) Uani d . 1 . . C
C22 0.5847(7) -0.0004(6) 0.48168(17) 0.0175(9) Uani d . 1 . . C
C23 0.5351(8) -0.0775(6) 0.42930(18) 0.0223(10) Uani d . 1 . . C
C24 0.7161(8) -0.1591(6) 0.40792(18) 0.0229(11) Uani d . 1 . . C
C25 0.8724(8) -0.1323(6) 0.44730(18) 0.0227(11) Uani d . 1 . . C
C26 0.4532(8) 0.0856(6) 0.52368(16) 0.0214(10) Uani d . 1 . . C
O2 0.9913(5) 0.0839(4) 0.59806(12) 0.0215(8) Uani d . 1 . . O
H12 -0.0961 0.4349 0.7517 0.027 Uiso calc R 1 . . H
H13 0.0890 0.3749 0.6695 0.022 Uiso calc R 1 . . H
H15 0.5832 0.2355 0.7682 0.029 Uiso calc R 1 . . H
H16 0.3747 0.2874 0.8466 0.034 Uiso calc R 1 . . H
H17 0.2741 0.1722 0.6103 0.025 Uiso d R 1 . . H
H21 0.8591 -0.0017 0.5223 0.024 Uiso calc R 1 . . H
H23 0.4027 -0.0750 0.4114 0.029 Uiso calc R 1 . . H
H24 0.7293 -0.2218 0.3727 0.030 Uiso calc R 1 . . H
H25 1.0123 -0.1737 0.4440 0.030 Uiso calc R 1 . . H
H26 0.3076 0.0982 0.5177 0.026 Uiso calc R 1 . . H
H2A 0.8869 0.1511 0.6042 0.026 Uiso d R 1 . . H
H2B 0.9824 0.0006 0.6228 0.026 Uiso d R 1 . . H
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_publ_flag
C12 N11 C16 116.4(4) no
N11 C12 C13 124.3(4) no
N11 C12 H12 117.9 no
C13 C12 H12 117.9 no
C14 C13 C12 118.6(4) no
C14 C13 H13 120.7 no
C12 C13 H13 120.7 no
C13 C14 C15 118.5(4) no
C13 C14 C17 124.2(4) no
C15 C14 C17 117.4(4) no
C16 C15 C14 117.9(4) no
C16 C15 H15 121.0 no
C14 C15 H15 121.0 no
N11 C16 C15 124.3(4) no
N11 C16 H16 117.8 no
C15 C16 H16 117.8 no
O1 C17 N17 123.2(4) no
O1 C17 C14 120.0(4) no
C14 C17 N17 116.8(4) y
C17 N17 N27 116.2(4) y
C17 N17 H17 123.6 no
N27 N17 H17 118.0 no
N17 N27 C26 116.5(4) y
C22 N21 C25 109.5(4) no
C22 N21 H21 125.2 no
C25 N21 H21 125.2 no
N21 C22 C23 107.5(4) no
N21 C22 C26 121.7(4) no
C23 C22 C26 130.4(4) no
C22 C23 C24 107.4(4) no
C22 C23 H23 126.3 no
C24 C23 H23 126.3 no
C25 C24 C23 107.6(4) no
C25 C24 H24 126.2 no
C23 C24 H24 126.2 no
N21 C25 C24 108.0(4) no
N21 C25 H25 126.0 no
C24 C25 H25 126.0 no
N27 C26 C22 117.9(4) y
N27 C26 H26 121.1 no
C22 C26 H26 121.1 no
H2A O2 H2B 103.7 no
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
N11 C12 . 1.333(6) no
N11 C16 . 1.339(7) no
C12 C13 . 1.387(6) no
C12 H12 . 0.95 no
C13 C14 . 1.377(6) no
C13 H13 . 0.95 no
C14 C15 . 1.406(6) no
C14 C17 . 1.497(6) y
C17 N17 . 1.345(5) y
N17 N27 . 1.393(5) y
N27 C26 . 1.289(5) y
C26 C22 . 1.442(6) y
C15 C16 . 1.382(6) no
C15 H15 . 0.95 no
C16 H16 . 0.95 no
C17 O1 . 1.240(6) no
N17 H17 . 0.88 no
N21 C22 . 1.365(6) y
C22 C23 . 1.393(6) y
C23 C24 . 1.397(7) y
C24 C25 . 1.382(7) y
C25 N21 . 1.366(5) y
N21 H21 . 0.88 no
C23 H23 . 0.95 no
C24 H24 . 0.95 no
C25 H25 . 0.95 no
C26 H26 . 0.95 no
O2 H2A . 0.84 no
O2 H2B . 0.84 no
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
O2 H2A O1 . 0.84 2.18 2.934(5) 150 y
O2 H2A N27 . 0.84 2.38 3.011(5) 133 y
N21 H21 O2 . 0.88 2.07 2.950(5) 174 y
N17 H17 O2 1_455 0.88 1.95 2.822(5) 173 y
O2 H2B N11 4_646 0.84 2.03 2.832(5) 159 y
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
_geom_torsion_publ_flag
C16 N11 C12 C13 1.1(7) no
N11 C12 C13 C14 -2.5(7) no
C12 C13 C14 C15 2.1(6) no
C12 C13 C14 C17 -177.6(4) no
C13 C14 C15 C16 -0.6(6) no
C17 C14 C15 C16 179.1(4) no
C12 N11 C16 C15 0.6(7) no
C14 C15 C16 N11 -0.8(7) no
C13 C14 C17 O1 149.0(5) no
C15 C14 C17 O1 -30.7(6) no
C13 C14 C17 N17 -32.6(6) y
C15 C14 C17 N17 147.6(4) no
O1 C17 N17 N27 9.1(6) no
C14 C17 N17 N27 -169.2(4) y
C17 N17 N27 C26 -178.9(4) y
C25 N21 C22 C23 0.2(5) no
C25 N21 C22 C26 174.5(4) no
N21 C22 C23 C24 -0.4(5) no
C26 C22 C23 C24 -174.0(4) no
C22 C23 C24 C25 0.4(5) no
C22 N21 C25 C24 0.0(5) no
C23 C24 C25 N21 -0.2(5) no
N17 N27 C26 C22 -172.1(4) y
N21 C22 C26 N27 6.4(6) no
N27 C26 C22 C23 179.3(4) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180980
