#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/84/2228408.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_2228408
loop_
_publ_author_name
'Ni, Lei'
'Zhao, Ji-Li'
'Wei, Hong'
_publ_section_title
;
 Aqua(4-nitrophthalato-κO¹)bis[2-(1H-pyrazol-3-yl-κN²)pyridine-κN]manganese(II)
 hemihydrate
;
_journal_coeditor_code           IM2225
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1550
_journal_paper_doi               10.1107/S1600536810045952
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'[Mn (C8 H3 N O6) (C8 H7 N3)2 (H2 O)], 0.5H2 O'
_chemical_formula_moiety         'C24 H19 Mn N7 O7, 0.5(H2 O)'
_chemical_formula_sum            'C24 H20 Mn N7 O7.5'
_chemical_formula_weight         581.41
_chemical_name_systematic
;
Aqua(4-nitrophthalato-κO¹)bis[2-(1H-pyrazol-3-yl-
κN²)pyridine-κN]manganese(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                96.275(2)
_cell_angle_beta                 112.485(2)
_cell_angle_gamma                96.902(2)
_cell_formula_units_Z            2
_cell_length_a                   10.5996(7)
_cell_length_b                   11.2654(7)
_cell_length_c                   11.9493(7)
_cell_measurement_reflns_used    4492
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.85
_cell_volume                     1289.94(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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13775
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_correction_T_min  0.9345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             594
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.555
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0376
_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)+(0.0650P)²+0.6953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                4112
_reflns_number_total             4492
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2225.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C24 H20 Mn1 N7 O7.5'
_cod_database_code               2228408
_cod_database_fobs_code          2228408
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
C C1 0.7173(4) 0.2731(3) 0.9226(3) 0.0712(8) Uani d . 1 . .
H H1 0.6343 0.2568 0.9323 0.085 Uiso calc R 1 . .
C C2 0.8448(4) 0.3131(3) 1.0143(3) 0.0697(8) Uani d . 1 . .
H H2 0.8668 0.3294 1.0983 0.084 Uiso calc R 1 . .
C C3 0.9359(3) 0.3247(2) 0.9554(2) 0.0518(6) Uani d . 1 . .
C C4 1.0853(3) 0.3638(2) 1.0005(2) 0.0537(6) Uani d . 1 . .
C C5 1.1703(4) 0.4045(3) 1.1239(2) 0.0695(8) Uani d . 1 . .
H H5 1.1328 0.4073 1.1828 0.083 Uiso calc R 1 . .
C C6 1.3098(4) 0.4403(3) 1.1578(3) 0.0831(10) Uani d . 1 . .
H H6 1.3680 0.4673 1.2401 0.100 Uiso calc R 1 . .
C C7 1.3632(4) 0.4362(3) 1.0692(3) 0.0802(9) Uani d . 1 . .
H H7 1.4576 0.4607 1.0903 0.096 Uiso calc R 1 . .
C C8 1.2730(3) 0.3948(3) 0.9483(3) 0.0670(7) Uani d . 1 . .
H H8 1.3090 0.3916 0.8884 0.080 Uiso calc R 1 . .
C C9 1.3004(3) 0.2422(3) 0.5695(3) 0.0635(7) Uani d . 1 . .
H H9 1.3674 0.2662 0.5403 0.076 Uiso calc R 1 . .
C C10 1.2660(3) 0.1287(3) 0.5905(3) 0.0611(7) Uani d . 1 . .
H H10 1.3037 0.0604 0.5786 0.073 Uiso calc R 1 . .
C C11 1.1618(2) 0.13717(19) 0.63382(19) 0.0406(4) Uani d . 1 . .
C C12 1.0839(2) 0.04615(18) 0.67283(18) 0.0404(4) Uani d . 1 . .
C C13 1.0928(3) -0.0766(2) 0.6586(2) 0.0526(6) Uani d . 1 . .
H H13 1.1490 -0.1049 0.6217 0.063 Uiso calc R 1 . .
C C14 1.0177(3) -0.1549(2) 0.6995(3) 0.0663(7) Uani d . 1 . .
H H14 1.0218 -0.2372 0.6906 0.080 Uiso calc R 1 . .
C C15 0.9309(3) 0.0111(2) 0.7633(3) 0.0688(8) Uani d . 1 . .
H H15 0.8747 0.0405 0.7995 0.083 Uiso calc R 1 . .
C C16 0.9367(4) -0.1107(3) 0.7536(3) 0.0761(8) Uani d . 1 . .
H H16 0.8861 -0.1620 0.7834 0.091 Uiso calc R 1 . .
C C17 0.6605(2) 0.2144(2) 0.5118(2) 0.0513(6) Uani d . 1 . .
C C18 0.5813(2) 0.1929(2) 0.3746(2) 0.0427(5) Uani d . 1 . .
C C19 0.4714(3) 0.0954(2) 0.3232(2) 0.0572(6) Uani d . 1 . .
H H19 0.4438 0.0523 0.3746 0.069 Uiso calc R 1 . .
C C20 0.4030(3) 0.0616(2) 0.1979(3) 0.0619(7) Uani d . 1 . .
H H20 0.3294 -0.0034 0.1639 0.074 Uiso calc R 1 . .
C C21 0.4462(2) 0.1264(2) 0.1246(2) 0.0545(6) Uani d . 1 . .
C C22 0.5544(2) 0.2235(2) 0.1721(2) 0.0479(5) Uani d . 1 . .
H H22 0.5820 0.2648 0.1197 0.058 Uiso calc R 1 . .
C C23 0.6216(2) 0.25915(18) 0.29779(19) 0.0400(4) Uani d . 1 . .
C C24 0.7320(2) 0.3719(2) 0.3445(2) 0.0462(5) Uani d . 1 . .
Mn Mn1 0.97367(3) 0.28597(3) 0.71009(3) 0.03701(12) Uani d . 1 . .
N N1 0.7320(2) 0.26121(19) 0.8159(2) 0.0564(5) Uani d . 1 . .
H H1A 0.6650 0.2366 0.7450 0.068 Uiso calc R 1 . .
N N2 0.8652(2) 0.29291(17) 0.83442(17) 0.0485(4) Uani d . 1 . .
N N3 1.1369(2) 0.35929(18) 0.91298(18) 0.0528(5) Uani d . 1 . .
N N4 1.22077(19) 0.31285(17) 0.59823(18) 0.0474(4) Uani d . 1 . .
H H4 1.2240 0.3884 0.5919 0.057 Uiso calc R 1 . .
N N5 1.13476(17) 0.25018(15) 0.63847(16) 0.0393(4) Uani d . 1 . .
N N6 1.0021(2) 0.08928(16) 0.72337(18) 0.0467(4) Uani d . 1 . .
N N7 0.3749(3) 0.0899(3) -0.0097(2) 0.0805(7) Uani d . 1 . .
O O1 0.5935(2) 0.2119(4) 0.5746(2) 0.1504(16) Uani d . 1 . .
O O2 0.78795(15) 0.22449(14) 0.54996(14) 0.0475(4) Uani d . 1 . .
O O3 0.7370(2) 0.44475(15) 0.43391(16) 0.0596(4) Uani d . 1 . .
O O4 0.8061(2) 0.38723(19) 0.2870(2) 0.0791(6) Uani d . 1 . .
O O5 0.4122(3) 0.1463(3) -0.0749(2) 0.1086(9) Uani d . 1 . .
O O6 0.2814(4) 0.0044(3) -0.0487(3) 0.1654(18) Uani d . 1 . .
O O1W 0.96188(16) 0.46463(14) 0.66095(15) 0.0479(4) Uani d D 1 . .
O O2W 0.5000 0.5000 0.5000 0.208(3) Uani d S 1 . .
H H1W 0.9011(17) 0.454(3) 0.5913(10) 0.080 Uiso d D 1 . .
H H2W 1.0347(14) 0.507(2) 0.670(2) 0.080 Uiso d 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'
Mn Mn 0.3368 0.7283 '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 . . 108.0(3) ?
N1 C1 H1 . . 126.0 ?
C2 C1 H1 . . 126.0 ?
C1 C2 C3 . . 105.2(2) ?
C1 C2 H2 . . 127.4 ?
C3 C2 H2 . . 127.4 ?
N2 C3 C2 . . 109.7(3) ?
N2 C3 C4 . . 117.4(2) ?
C2 C3 C4 . . 132.9(2) ?
N3 C4 C5 . . 121.6(3) ?
N3 C4 C3 . . 115.1(2) ?
C5 C4 C3 . . 123.3(2) ?
C6 C5 C4 . . 119.2(3) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C5 C6 C7 . . 119.5(3) ?
C5 C6 H6 . . 120.2 ?
C7 C6 H6 . . 120.2 ?
C6 C7 C8 . . 118.3(3) ?
C6 C7 H7 . . 120.9 ?
C8 C7 H7 . . 120.9 ?
N3 C8 C7 . . 123.3(3) ?
N3 C8 H8 . . 118.3 ?
C7 C8 H8 . . 118.3 ?
N4 C9 C10 . . 108.0(2) ?
N4 C9 H9 . . 126.0 ?
C10 C9 H9 . . 126.0 ?
C9 C10 C11 . . 105.0(2) ?
C9 C10 H10 . . 127.5 ?
C11 C10 H10 . . 127.5 ?
N5 C11 C10 . . 110.3(2) ?
N5 C11 C12 . . 118.75(18) ?
C10 C11 C12 . . 131.0(2) ?
N6 C12 C13 . . 121.9(2) ?
N6 C12 C11 . . 115.00(18) ?
C13 C12 C11 . . 123.1(2) ?
C14 C13 C12 . . 119.1(2) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
C16 C14 C13 . . 119.2(2) ?
C16 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
N6 C15 C16 . . 123.2(3) ?
N6 C15 H15 . . 118.4 ?
C16 C15 H15 . . 118.4 ?
C14 C16 C15 . . 118.9(3) ?
C14 C16 H16 . . 120.6 ?
C15 C16 H16 . . 120.6 ?
O1 C17 O2 . . 125.8(2) ?
O1 C17 C18 . . 117.3(2) ?
O2 C17 C18 . . 116.67(19) ?
C19 C18 C23 . . 119.6(2) ?
C19 C18 C17 . . 117.4(2) ?
C23 C18 C17 . . 122.66(19) ?
C20 C19 C18 . . 121.1(2) ?
C20 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
C21 C20 C19 . . 118.2(2) ?
C21 C20 H20 . . 120.9 ?
C19 C20 H20 . . 120.9 ?
C20 C21 C22 . . 122.3(2) ?
C20 C21 N7 . . 118.6(2) ?
C22 C21 N7 . . 119.0(2) ?
C21 C22 C23 . . 119.7(2) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C22 C23 C18 . . 119.03(19) ?
C22 C23 C24 . . 117.40(19) ?
C18 C23 C24 . . 123.52(19) ?
O4 C24 O3 . . 125.3(2) ?
O4 C24 C23 . . 116.6(2) ?
O3 C24 C23 . . 118.0(2) ?
O2 Mn1 O1W . . 86.45(6) ?
O2 Mn1 N2 . . 93.74(7) ?
O1W Mn1 N2 . . 99.70(7) ?
O2 Mn1 N5 . . 101.41(6) ?
O1W Mn1 N5 . . 95.17(6) ?
N2 Mn1 N5 . . 159.38(7) ?
O2 Mn1 N6 . . 89.68(7) ?
O1W Mn1 N6 . . 166.14(7) ?
N2 Mn1 N6 . . 93.83(7) ?
N5 Mn1 N6 . . 72.55(6) ?
O2 Mn1 N3 . . 164.44(7) ?
O1W Mn1 N3 . . 94.04(7) ?
N2 Mn1 N3 . . 70.82(8) ?
N5 Mn1 N3 . . 94.05(7) ?
N6 Mn1 N3 . . 93.24(7) ?
C1 N1 N2 . . 110.7(2) ?
C1 N1 H1A . . 124.6 ?
N2 N1 H1A . . 124.6 ?
C3 N2 N1 . . 106.40(18) ?
C3 N2 Mn1 . . 120.74(17) ?
N1 N2 Mn1 . . 132.63(15) ?
C8 N3 C4 . . 118.0(2) ?
C8 N3 Mn1 . . 126.27(17) ?
C4 N3 Mn1 . . 115.70(17) ?
C9 N4 N5 . . 111.07(19) ?
C9 N4 H4 . . 124.5 ?
N5 N4 H4 . . 124.5 ?
C11 N5 N4 . . 105.65(16) ?
C11 N5 Mn1 . . 116.41(13) ?
N4 N5 Mn1 . . 137.92(13) ?
C15 N6 C12 . . 117.8(2) ?
C15 N6 Mn1 . . 125.06(16) ?
C12 N6 Mn1 . . 116.60(14) ?
O6 N7 O5 . . 123.3(3) ?
O6 N7 C21 . . 117.6(3) ?
O5 N7 C21 . . 119.1(3) ?
C17 O2 Mn1 . . 142.44(15) ?
Mn1 O1W H1W . . 106(2) ?
Mn1 O1W H2W . . 117(2) ?
H1W O1W H2W . . 115(2) ?
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 . 1.338(3) ?
C1 C2 . 1.357(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.398(4) ?
C2 H2 . 0.9300 ?
C3 N2 . 1.332(3) ?
C3 C4 . 1.456(4) ?
C4 N3 . 1.352(3) ?
C4 C5 . 1.390(4) ?
C5 C6 . 1.370(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.378(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.382(4) ?
C7 H7 . 0.9300 ?
C8 N3 . 1.334(4) ?
C8 H8 . 0.9300 ?
C9 N4 . 1.337(3) ?
C9 C10 . 1.364(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.396(3) ?
C10 H10 . 0.9300 ?
C11 N5 . 1.338(3) ?
C11 C12 . 1.465(3) ?
C12 N6 . 1.338(3) ?
C12 C13 . 1.393(3) ?
C13 C14 . 1.370(4) ?
C13 H13 . 0.9300 ?
C14 C16 . 1.364(4) ?
C14 H14 . 0.9300 ?
C15 N6 . 1.334(3) ?
C15 C16 . 1.375(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 O1 . 1.216(3) ?
C17 O2 . 1.235(3) ?
C17 C18 . 1.504(3) ?
C18 C19 . 1.393(3) ?
C18 C23 . 1.398(3) ?
C19 C20 . 1.375(4) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.370(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.378(3) ?
C21 N7 . 1.473(3) ?
C22 C23 . 1.380(3) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.511(3) ?
C24 O4 . 1.235(3) ?
C24 O3 . 1.253(3) ?
Mn1 O2 . 2.1255(15) ?
Mn1 O1W . 2.1619(15) ?
Mn1 N2 . 2.1995(17) ?
Mn1 N5 . 2.2401(16) ?
Mn1 N6 . 2.2861(18) ?
Mn1 N3 . 2.359(2) ?
N1 N2 . 1.339(3) ?
N1 H1A . 0.8600 ?
N4 N5 . 1.347(2) ?
N4 H4 . 0.8600 ?
N7 O6 . 1.203(4) ?
N7 O5 . 1.203(4) ?
O1W H1W . 0.820(12) ?
O1W H2W . 0.82(2) ?
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
O1W H2W O4 2_766 0.82(2) 1.80(2) 2.615(2) 171(3)
N1 H1A O1 . 0.86 1.86 2.644(3) 151.7
