#------------------------------------------------------------------------------
#$Date: 2017-11-25 02:32:52 +0200 (Sat, 25 Nov 2017) $
#$Revision: 203559 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/87/2228755.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_2228755
loop_
_publ_author_name
'Ni, Lei'
'Zhao, Ji-Li'
'Wei, Hong'
_publ_section_title
;
 Aqua(4-nitrophthalato)bis[2-(1H-pyrazol-3-yl)pyridine]zinc(II)
 hemihydrate
;
_journal_coeditor_code           IM2226
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m105
_journal_paper_doi               10.1107/S1600536810051949
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac
'[Zn (C8 H3 N O6) (C8 H7 N3)2 (H2 O)], 0.5H2 O'
_chemical_formula_moiety         'C24 H19 N7 O7 Zn, 0.5(H2 O)'
_chemical_formula_sum            'C24 H20 N7 O7.5 Zn'
_chemical_formula_weight         591.84
_chemical_name_systematic
;
Aqua(4-nitrophthalato)bis[2-(1H-pyrazol-3-yl)pyridine]zinc(II)
hemihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.508(3)
_cell_angle_beta                 112.091(3)
_cell_angle_gamma                96.366(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4284(6)
_cell_length_b                   11.1844(7)
_cell_length_c                   11.9656(8)
_cell_measurement_reflns_used    4528
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.40
_cell_volume                     1266.84(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_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      294(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega 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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9062
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_T_max  0.9221
_exptl_absorpt_correction_T_min  0.8863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.422
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0660P)²+0.7068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                3825
_reflns_number_total             4258
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2226.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Marking attached hydrogens atoms.

 Antanas Vaitkus,
 2017-11-25
;
_cod_original_formula_sum        'C24 H20 N7 O7.5 Zn1'
_cod_database_code               2228755
_cod_database_fobs_code          2228755
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_attached_hydrogens
C C1 0.7155(4) 0.7772(3) 0.9195(3) 0.0652(9) Uani d . 1 . . 0
H H1 0.6311 0.7613 0.9291 0.078 Uiso calc R 1 . . 0
C C2 0.8440(4) 0.8158(3) 1.0110(3) 0.0618(9) Uani d . 1 . . 0
H H2 0.8654 0.8318 1.0946 0.074 Uiso calc R 1 . . 0
C C3 0.9371(3) 0.8262(2) 0.9526(3) 0.0471(7) Uani d . 1 . . 0
C C4 1.0889(3) 0.8628(2) 0.9968(3) 0.0476(7) Uani d . 1 . . 0
C C5 1.1747(4) 0.9022(3) 1.1197(3) 0.0610(8) Uani d . 1 . . 0
H H5 1.1367 0.9060 1.1788 0.073 Uiso calc R 1 . . 0
C C6 1.3160(4) 0.9354(3) 1.1522(3) 0.0719(10) Uani d . 1 . . 0
H H6 1.3755 0.9618 1.2339 0.086 Uiso calc R 1 . . 0
C C7 1.3695(4) 0.9292(3) 1.0618(3) 0.0708(10) Uani d . 1 . . 0
H H7 1.4651 0.9517 1.0817 0.085 Uiso calc R 1 . . 0
C C8 1.2775(4) 0.8889(3) 0.9417(3) 0.0589(8) Uani d . 1 . . 0
H H8 1.3136 0.8841 0.8814 0.071 Uiso calc R 1 . . 0
C C9 1.2913(3) 0.7454(3) 0.5661(3) 0.0594(8) Uani d . 1 . . 0
H H9 1.3580 0.7702 0.5356 0.071 Uiso calc R 1 . . 0
C C10 1.2595(3) 0.6312(3) 0.5882(3) 0.0576(8) Uani d . 1 . . 0
H H10 1.2987 0.5629 0.5755 0.069 Uiso calc R 1 . . 0
C C11 1.1556(3) 0.6392(2) 0.6339(2) 0.0381(5) Uani d . 1 . . 0
C C12 1.0801(3) 0.5491(2) 0.6763(2) 0.0369(5) Uani d . 1 . . 0
C C13 1.0886(3) 0.4254(2) 0.6620(3) 0.0493(7) Uani d . 1 . . 0
H H13 1.1427 0.3953 0.6223 0.059 Uiso calc R 1 . . 0
C C14 1.0159(4) 0.3486(3) 0.7075(3) 0.0621(9) Uani d . 1 . . 0
H H14 1.0200 0.2656 0.6988 0.075 Uiso calc R 1 . . 0
C C15 0.9378(4) 0.3948(3) 0.7654(4) 0.0680(9) Uani d . 1 . . 0
H H15 0.8888 0.3442 0.7977 0.082 Uiso calc R 1 . . 0
C C16 0.9322(4) 0.5181(3) 0.7755(3) 0.0606(8) Uani d . 1 . . 0
H H16 0.8783 0.5491 0.8150 0.073 Uiso calc R 1 . . 0
C C17 0.6685(3) 0.7186(3) 0.5137(3) 0.0499(7) Uani d . 1 . . 0
C C18 0.5894(3) 0.6933(2) 0.3769(2) 0.0403(6) Uani d . 1 . . 0
C C19 0.4792(3) 0.5955(3) 0.3277(3) 0.0539(7) Uani d . 1 . . 0
H H19 0.4518 0.5534 0.3799 0.065 Uiso calc R 1 . . 0
C C20 0.4097(3) 0.5596(3) 0.2034(3) 0.0586(8) Uani d . 1 . . 0
H H20 0.3366 0.4936 0.1711 0.070 Uiso calc R 1 . . 0
C C21 0.4512(3) 0.6235(3) 0.1282(3) 0.0496(7) Uani d . 1 . . 0
C C22 0.5606(3) 0.7203(2) 0.1733(2) 0.0431(6) Uani d . 1 . . 0
H H22 0.5887 0.7600 0.1200 0.052 Uiso calc R 1 . . 0
C C23 0.6285(2) 0.7579(2) 0.2984(2) 0.0371(5) Uani d . 1 . . 0
C C24 0.7389(3) 0.8724(2) 0.3428(3) 0.0442(6) Uani d . 1 . . 0
Zn Zn1 0.97417(3) 0.78410(2) 0.71551(3) 0.03624(12) Uani d . 1 . . 0
N N1 0.3763(3) 0.5867(3) -0.0053(3) 0.0720(8) Uani d . 1 . . 0
N N2 0.7314(3) 0.7660(2) 0.8127(2) 0.0519(6) Uani d . 1 . . 0
H H2A 0.6641 0.7428 0.7420 0.062 Uiso calc R 1 . . 0
N N3 0.8669(3) 0.7961(2) 0.8318(2) 0.0452(5) Uani d . 1 . . 0
N N4 1.1400(3) 0.8564(2) 0.9082(2) 0.0477(6) Uani d . 1 . . 0
N N5 1.2091(2) 0.8153(2) 0.5964(2) 0.0442(5) Uani d . 1 . . 0
H H5A 1.2100 0.8911 0.5895 0.053 Uiso calc R 1 . . 0
N N6 1.1256(2) 0.75232(18) 0.63868(19) 0.0374(5) Uani d . 1 . . 0
N N7 1.0006(2) 0.59453(19) 0.7312(2) 0.0423(5) Uani d . 1 . . 0
O O1 0.95913(19) 0.95872(16) 0.67148(17) 0.0420(4) Uani d D 1 . . 0
O O2 0.5984(3) 0.7250(6) 0.5755(3) 0.165(2) Uani d . 1 . . 0
O O3 0.79649(18) 0.72281(17) 0.55259(17) 0.0433(4) Uani d . 1 . . 0
O O4 0.7478(3) 0.94256(18) 0.43546(19) 0.0594(6) Uani d . 1 . . 0
O O5 0.8072(3) 0.8910(2) 0.2798(3) 0.0751(7) Uani d . 1 . . 0
O O6 0.4156(3) 0.6389(3) -0.0729(2) 0.0957(10) Uani d . 1 . . 0
O O7 0.2773(4) 0.5050(4) -0.0427(3) 0.1448(18) Uani d . 1 . . 0
O O1W 0.5000 0.0000 0.5000 0.198(4) Uani d S 1 . . 2
H H1W 0.901(2) 0.943(3) 0.6007(10) 0.080 Uiso d D 1 . . 0
H H2W 1.031(2) 1.004(3) 0.681(3) 0.080 Uiso d D 1 . . 0
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'
Zn Zn 0.2839 1.4301 '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
N2 C1 C2 . . 108.1(3) ?
N2 C1 H1 . . 126.0 ?
C2 C1 H1 . . 126.0 ?
C1 C2 C3 . . 105.1(3) ?
C1 C2 H2 . . 127.4 ?
C3 C2 H2 . . 127.4 ?
N3 C3 C2 . . 109.9(3) ?
N3 C3 C4 . . 116.7(2) ?
C2 C3 C4 . . 133.4(3) ?
N4 C4 C5 . . 122.4(3) ?
N4 C4 C3 . . 114.5(2) ?
C5 C4 C3 . . 123.1(3) ?
C6 C5 C4 . . 118.8(3) ?
C6 C5 H5 . . 120.6 ?
C4 C5 H5 . . 120.6 ?
C5 C6 C7 . . 119.3(3) ?
C5 C6 H6 . . 120.4 ?
C7 C6 H6 . . 120.4 ?
C8 C7 C6 . . 118.5(4) ?
C8 C7 H7 . . 120.8 ?
C6 C7 H7 . . 120.8 ?
N4 C8 C7 . . 123.2(3) ?
N4 C8 H8 . . 118.4 ?
C7 C8 H8 . . 118.4 ?
N5 C9 C10 . . 107.6(3) ?
N5 C9 H9 . . 126.2 ?
C10 C9 H9 . . 126.2 ?
C9 C10 C11 . . 105.1(3) ?
C9 C10 H10 . . 127.5 ?
C11 C10 H10 . . 127.5 ?
N6 C11 C10 . . 110.3(2) ?
N6 C11 C12 . . 118.0(2) ?
C10 C11 C12 . . 131.8(2) ?
N7 C12 C13 . . 121.8(3) ?
N7 C12 C11 . . 114.8(2) ?
C13 C12 C11 . . 123.4(2) ?
C14 C13 C12 . . 118.9(3) ?
C14 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C15 C14 C13 . . 119.5(3) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C14 C15 C16 . . 119.0(3) ?
C14 C15 H15 . . 120.5 ?
C16 C15 H15 . . 120.5 ?
N7 C16 C15 . . 122.8(3) ?
N7 C16 H16 . . 118.6 ?
C15 C16 H16 . . 118.6 ?
O2 C17 O3 . . 126.1(3) ?
O2 C17 C18 . . 116.8(3) ?
O3 C17 C18 . . 117.0(2) ?
C19 C18 C23 . . 119.3(3) ?
C19 C18 C17 . . 117.7(3) ?
C23 C18 C17 . . 122.8(2) ?
C20 C19 C18 . . 121.4(3) ?
C20 C19 H19 . . 119.3 ?
C18 C19 H19 . . 119.3 ?
C21 C20 C19 . . 118.3(3) ?
C21 C20 H20 . . 120.9 ?
C19 C20 H20 . . 120.9 ?
C20 C21 C22 . . 122.1(3) ?
C20 C21 N1 . . 118.7(3) ?
C22 C21 N1 . . 119.2(3) ?
C21 C22 C23 . . 119.5(3) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C22 C23 C18 . . 119.3(2) ?
C22 C23 C24 . . 117.3(2) ?
C18 C23 C24 . . 123.3(2) ?
O5 C24 O4 . . 125.7(3) ?
O5 C24 C23 . . 116.6(2) ?
O4 C24 C23 . . 117.6(3) ?
O1 Zn1 N3 . . 96.46(8) ?
O1 Zn1 O3 . . 86.38(7) ?
N3 Zn1 O3 . . 96.57(9) ?
O1 Zn1 N6 . . 94.67(8) ?
N3 Zn1 N6 . . 163.63(9) ?
O3 Zn1 N6 . . 96.08(7) ?
O1 Zn1 N7 . . 168.95(8) ?
N3 Zn1 N7 . . 94.18(9) ?
O3 Zn1 N7 . . 89.49(8) ?
N6 Zn1 N7 . . 75.57(8) ?
O1 Zn1 N4 . . 93.00(8) ?
N3 Zn1 N4 . . 73.48(9) ?
O3 Zn1 N4 . . 169.91(8) ?
N6 Zn1 N4 . . 94.01(8) ?
N7 Zn1 N4 . . 92.85(8) ?
O7 N1 O6 . . 122.6(3) ?
O7 N1 C21 . . 118.0(4) ?
O6 N1 C21 . . 119.4(3) ?
N3 N2 C1 . . 110.5(3) ?
N3 N2 H2A . . 124.7 ?
C1 N2 H2A . . 124.7 ?
C3 N3 N2 . . 106.3(2) ?
C3 N3 Zn1 . . 120.6(2) ?
N2 N3 Zn1 . . 132.65(19) ?
C8 N4 C4 . . 117.9(3) ?
C8 N4 Zn1 . . 127.8(2) ?
C4 N4 Zn1 . . 114.3(2) ?
N6 N5 C9 . . 111.4(2) ?
N6 N5 H5A . . 124.3 ?
C9 N5 H5A . . 124.3 ?
C11 N6 N5 . . 105.7(2) ?
C11 N6 Zn1 . . 115.52(17) ?
N5 N6 Zn1 . . 138.68(16) ?
C16 N7 C12 . . 118.1(2) ?
C16 N7 Zn1 . . 126.03(19) ?
C12 N7 Zn1 . . 115.32(17) ?
Zn1 O1 H1W . . 101(3) ?
Zn1 O1 H2W . . 119(3) ?
H1W O1 H2W . . 114(3) ?
C17 O3 Zn1 . . 139.12(19) ?
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 N2 . 1.343(4) ?
C1 C2 . 1.357(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.396(4) ?
C2 H2 . 0.9300 ?
C3 N3 . 1.334(4) ?
C3 C4 . 1.460(4) ?
C4 N4 . 1.352(4) ?
C4 C5 . 1.390(4) ?
C5 C6 . 1.369(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.390(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.382(5) ?
C7 H7 . 0.9300 ?
C8 N4 . 1.330(4) ?
C8 H8 . 0.9300 ?
C9 N5 . 1.341(4) ?
C9 C10 . 1.363(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.393(4) ?
C10 H10 . 0.9300 ?
C11 N6 . 1.336(3) ?
C11 C12 . 1.460(4) ?
C12 N7 . 1.342(3) ?
C12 C13 . 1.391(4) ?
C13 C14 . 1.371(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.359(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.379(4) ?
C15 H15 . 0.9300 ?
C16 N7 . 1.333(4) ?
C16 H16 . 0.9300 ?
C17 O2 . 1.221(4) ?
C17 O3 . 1.231(3) ?
C17 C18 . 1.506(4) ?
C18 C19 . 1.390(4) ?
C18 C23 . 1.396(4) ?
C19 C20 . 1.374(5) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.371(5) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.376(4) ?
C21 N1 . 1.474(4) ?
C22 C23 . 1.383(4) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.518(3) ?
C24 O5 . 1.235(4) ?
C24 O4 . 1.250(4) ?
Zn1 O1 . 2.0871(18) ?
Zn1 N3 . 2.089(2) ?
Zn1 O3 . 2.0981(18) ?
Zn1 N6 . 2.147(2) ?
Zn1 N7 . 2.188(2) ?
Zn1 N4 . 2.287(2) ?
N1 O7 . 1.204(4) ?
N1 O6 . 1.211(4) ?
N2 N3 . 1.341(3) ?
N2 H2A . 0.8600 ?
N5 N6 . 1.337(3) ?
N5 H5A . 0.8600 ?
O1 H1W . 0.820(13) ?
O1 H2W . 0.82(3) ?
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
O1 H2W O5 2_776 0.82(3) 1.81(3) 2.627(3) 174(3)
N5 H5A O4 2_776 0.86 1.95 2.788(3) 166
N2 H2A O2 . 0.86 1.82 2.606(4) 150
