#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/79/2217923.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_2217923
loop_
_publ_author_name
'Huang, Jing'
'Hu, Wei-Ping'
'An, Zhe'
_publ_section_title
;Poly[[bis[μ₂-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato]manganese(II)]
 dihydrate]
;
_journal_coeditor_code           HB2703
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m547
_journal_paper_doi               10.1107/S1600536808006533
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Mn (C14 H16 N5 O3)2], 2H2 O'
_chemical_formula_moiety         'C28 H32 Mn N10 O6, 2(H2 O)'
_chemical_formula_sum            'C28 H36 Mn N10 O8'
_chemical_formula_weight         695.58
_chemical_name_systematic
;
Poly[[bis[μ₂-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-
dihydropyrido[2,3-d]pyrimidine-6-carboxylato]manganese(II)] dihydrate]
;
_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                 99.6170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.0422(2)
_cell_length_b                   21.5673(8)
_cell_length_c                   12.7395(5)
_cell_measurement_reflns_used    4747
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.49
_cell_volume                     1636.80(10)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10030
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             718.0
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.975
_refine_diff_density_min         -0.478
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3938
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0605
_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)+(0.1066P)²+1.0983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.1912
_reflns_number_gt                3465
_reflns_number_total             3938
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2703.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217923
_cod_database_fobs_code          2217923
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
Mn Mn1 0.5000 0.5000 0.5000 0.02831(19) Uani d S 1
O O1W 0.388(4) 0.5235(7) 0.9613(10) 0.244(9) Uani d P 0.50
O O1 0.7068(3) 0.49893(7) 0.38228(16) 0.0341(4) Uani d . 1
O O2W -0.081(2) 0.4426(8) 0.9246(7) 0.194(6) Uani d P 0.50
O O2 0.8721(5) 0.51863(13) 0.2451(2) 0.0717(8) Uani d . 1
O O3 0.3574(3) 0.58106(8) 0.41354(14) 0.0378(4) Uani d . 1
N N1 0.5078(5) 0.67158(12) 0.1504(2) 0.0533(7) Uani d . 1
N N2 -0.0007(4) 0.73723(11) 0.2985(2) 0.0464(6) Uani d . 1
N N3 0.2395(4) 0.74681(10) 0.16596(18) 0.0432(5) Uani d . 1
N N4 -0.0102(4) 0.82368(10) 0.19027(19) 0.0384(5) Uani d . 1
N N5 -0.2339(3) 0.93726(9) 0.11005(17) 0.0322(4) Uani d D 1
H H5N -0.140(4) 0.9649(12) 0.146(2) 0.048 Uiso d D 1
C C1 0.7282(4) 0.52991(11) 0.3018(2) 0.0358(5) Uani d . 1
C C2 0.5782(4) 0.58537(11) 0.2731(2) 0.0354(5) Uani d . 1
C C3 0.4044(4) 0.60559(10) 0.33118(19) 0.0313(5) Uani d . 1
C C4 0.2852(4) 0.66087(11) 0.28824(19) 0.0336(5) Uani d . 1
C C5 0.1042(5) 0.68542(12) 0.3304(2) 0.0425(6) Uani d . 1
H H5A 0.0546 0.6635 0.3848 0.051 Uiso calc R 1
C C6 0.0805(4) 0.76813(12) 0.2189(2) 0.0360(5) Uani d . 1
C C7 0.3383(5) 0.69362(12) 0.2010(2) 0.0395(6) Uani d . 1
C C8 0.6170(5) 0.61896(14) 0.1875(2) 0.0496(7) Uani d . 1
H H8A 0.7282 0.6046 0.1512 0.059 Uiso calc R 1
C C9 0.5717(8) 0.7043(2) 0.0566(3) 0.0725(12) Uani d . 1
H H9A 0.5531 0.7486 0.0645 0.087 Uiso calc R 1
H H9B 0.7285 0.6963 0.0537 0.087 Uiso calc R 1
C C10 0.4373(10) 0.6840(4) -0.0400(5) 0.116(2) Uani d . 1
H H10A 0.4583 0.6403 -0.0488 0.174 Uiso calc R 1
H H10B 0.4811 0.7059 -0.0989 0.174 Uiso calc R 1
H H10C 0.2822 0.6923 -0.0375 0.174 Uiso calc R 1
C C11 -0.1446(6) 0.85820(14) 0.2560(2) 0.0499(7) Uani d . 1
H H11A -0.0477 0.8852 0.3045 0.060 Uiso calc R 1
H H11B -0.2170 0.8295 0.2980 0.060 Uiso calc R 1
C C12 -0.3226(5) 0.89702(13) 0.1855(2) 0.0433(6) Uani d . 1
H H12A -0.4326 0.8693 0.1460 0.052 Uiso calc R 1
H H12B -0.3996 0.9225 0.2308 0.052 Uiso calc R 1
C C13 -0.1018(4) 0.89946(12) 0.0466(2) 0.0372(5) Uani d . 1
H H13A -0.0347 0.9264 -0.0003 0.045 Uiso calc R 1
H H13B -0.2015 0.8710 0.0025 0.045 Uiso calc R 1
C C14 0.0812(4) 0.86281(12) 0.1146(2) 0.0382(6) Uani d . 1
H H14A 0.1573 0.8371 0.0693 0.046 Uiso calc R 1
H H14B 0.1906 0.8911 0.1530 0.046 Uiso calc R 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
O1 Mn1 O1 . 3_666 180.0
O1 Mn1 O3 . . 83.09(6)
O1 Mn1 O3 3_666 . 96.91(6)
O1 Mn1 O3 . 3_666 96.91(6)
O1 Mn1 O3 3_666 3_666 83.09(6)
O3 Mn1 O3 . 3_666 180.0
O1 Mn1 N5 . 4_676 90.17(7)
O1 Mn1 N5 3_666 4_676 89.83(7)
O3 Mn1 N5 . 4_676 90.74(7)
O3 Mn1 N5 3_666 4_676 89.26(7)
O1 Mn1 N5 . 2_545 89.83(7)
O1 Mn1 N5 3_666 2_545 90.17(7)
O3 Mn1 N5 . 2_545 89.26(7)
O3 Mn1 N5 3_666 2_545 90.73(7)
N5 Mn1 N5 4_676 2_545 180.0
C1 O1 Mn1 . . 137.22(16)
C3 O3 Mn1 . . 129.93(16)
C8 N1 C7 . . 118.7(2)
C8 N1 C9 . . 119.8(3)
C7 N1 C9 . . 121.4(2)
C5 N2 C6 . . 115.3(2)
C7 N3 C6 . . 116.3(2)
C6 N4 C14 . . 120.9(2)
C6 N4 C11 . . 122.6(2)
C14 N4 C11 . . 113.1(2)
C12 N5 C13 . . 108.90(19)
C12 N5 Mn1 . 2 116.15(15)
C13 N5 Mn1 . 2 111.54(14)
C12 N5 H5N . . 110(2)
C13 N5 H5N . . 107(2)
Mn1 N5 H5N 2 . 103(2)
O2 C1 O1 . . 123.4(2)
O2 C1 C2 . . 117.6(2)
O1 C1 C2 . . 118.9(2)
C8 C2 C3 . . 119.0(2)
C8 C2 C1 . . 116.1(2)
C3 C2 C1 . . 124.9(2)
O3 C3 C2 . . 126.0(2)
O3 C3 C4 . . 119.8(2)
C2 C3 C4 . . 114.3(2)
C7 C4 C5 . . 114.3(2)
C7 C4 C3 . . 123.3(2)
C5 C4 C3 . . 122.4(2)
N2 C5 C4 . . 124.8(2)
N2 C5 H5A . . 117.6
C4 C5 H5A . . 117.6
N4 C6 N3 . . 117.5(2)
N4 C6 N2 . . 117.0(2)
N3 C6 N2 . . 125.4(2)
N3 C7 N1 . . 117.7(2)
N3 C7 C4 . . 123.4(2)
N1 C7 C4 . . 118.9(2)
N1 C8 C2 . . 125.8(3)
N1 C8 H8A . . 117.1
C2 C8 H8A . . 117.1
C10 C9 N1 . . 111.2(5)
C10 C9 H9A . . 109.4
N1 C9 H9A . . 109.4
C10 C9 H9B . . 109.4
N1 C9 H9B . . 109.4
H9A C9 H9B . . 108.0
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
N4 C11 C12 . . 110.2(2)
N4 C11 H11A . . 109.6
C12 C11 H11A . . 109.6
N4 C11 H11B . . 109.6
C12 C11 H11B . . 109.6
H11A C11 H11B . . 108.1
N5 C12 C11 . . 114.3(2)
N5 C12 H12A . . 108.7
C11 C12 H12A . . 108.7
N5 C12 H12B . . 108.7
C11 C12 H12B . . 108.7
H12A C12 H12B . . 107.6
N5 C13 C14 . . 112.8(2)
N5 C13 H13A . . 109.0
C14 C13 H13A . . 109.0
N5 C13 H13B . . 109.0
C14 C13 H13B . . 109.0
H13A C13 H13B . . 107.8
N4 C14 C13 . . 111.1(2)
N4 C14 H14A . . 109.4
C13 C14 H14A . . 109.4
N4 C14 H14B . . 109.4
C13 C14 H14B . . 109.4
H14A C14 H14B . . 108.0
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
Mn1 O1 . 2.106(2) y
Mn1 O1 3_666 2.106(2) ?
Mn1 O3 . 2.1667(16) y
Mn1 O3 3_666 2.1667(16) ?
Mn1 N5 4_676 2.372(2) y
Mn1 N5 2_545 2.3723(19) ?
O1 C1 . 1.248(3) ?
O2 C1 . 1.244(3) ?
O3 C3 . 1.249(3) ?
N1 C8 . 1.357(3) ?
N1 C7 . 1.382(4) ?
N1 C9 . 1.493(4) ?
N2 C5 . 1.315(3) ?
N2 C6 . 1.371(4) ?
N3 C7 . 1.335(3) ?
N3 C6 . 1.344(3) ?
N4 C6 . 1.343(3) ?
N4 C14 . 1.457(3) ?
N4 C11 . 1.463(3) ?
N5 C12 . 1.461(3) ?
N5 C13 . 1.474(3) ?
N5 Mn1 2 2.3723(19) ?
N5 H5N . 0.90(3) ?
C1 C2 . 1.508(3) ?
C2 C8 . 1.361(4) ?
C2 C3 . 1.450(3) ?
C3 C4 . 1.452(3) ?
C4 C7 . 1.399(3) ?
C4 C5 . 1.400(4) ?
C5 H5A . 0.9300 ?
C8 H8A . 0.9300 ?
C9 C10 . 1.425(8) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.531(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.510(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
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
N5 H5N O2 2_655 0.893(10) 2.268(12) 3.149(3) 169(3) 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
O3 Mn1 O1 C1 . -1.4(3)
O3 Mn1 O1 C1 3_666 178.6(3)
N5 Mn1 O1 C1 4_676 -92.1(3)
N5 Mn1 O1 C1 2_545 87.9(3)
O1 Mn1 O3 C3 . 1.4(2)
O1 Mn1 O3 C3 3_666 -178.6(2)
N5 Mn1 O3 C3 4_676 91.5(2)
N5 Mn1 O3 C3 2_545 -88.5(2)
Mn1 O1 C1 O2 . 179.3(2)
Mn1 O1 C1 C2 . 1.5(4)
O2 C1 C2 C8 . -1.0(4)
O1 C1 C2 C8 . 177.0(3)
O2 C1 C2 C3 . -179.1(3)
O1 C1 C2 C3 . -1.2(4)
Mn1 O3 C3 C2 . -1.8(4)
Mn1 O3 C3 C4 . -179.39(16)
C8 C2 C3 O3 . -176.6(3)
C1 C2 C3 O3 . 1.5(4)
C8 C2 C3 C4 . 1.1(4)
C1 C2 C3 C4 . 179.2(2)
O3 C3 C4 C7 . 175.3(2)
C2 C3 C4 C7 . -2.5(4)
O3 C3 C4 C5 . -5.6(4)
C2 C3 C4 C5 . 176.6(3)
C6 N2 C5 C4 . -0.7(5)
C7 C4 C5 N2 . -5.0(4)
C3 C4 C5 N2 . 175.8(3)
C14 N4 C6 N3 . -8.0(4)
C11 N4 C6 N3 . -165.6(3)
C14 N4 C6 N2 . 173.4(3)
C11 N4 C6 N2 . 15.8(4)
C7 N3 C6 N4 . 175.3(3)
C7 N3 C6 N2 . -6.2(4)
C5 N2 C6 N4 . -174.7(3)
C5 N2 C6 N3 . 6.8(4)
C6 N3 C7 N1 . -177.9(3)
C6 N3 C7 C4 . -0.5(4)
C8 N1 C7 N3 . 177.3(3)
C9 N1 C7 N3 . -2.9(5)
C8 N1 C7 C4 . -0.1(5)
C9 N1 C7 C4 . 179.7(3)
C5 C4 C7 N3 . 5.6(4)
C3 C4 C7 N3 . -175.2(3)
C5 C4 C7 N1 . -177.1(3)
C3 C4 C7 N1 . 2.1(4)
C7 N1 C8 C2 . -1.3(5)
C9 N1 C8 C2 . 178.8(4)
C3 C2 C8 N1 . 0.8(5)
C1 C2 C8 N1 . -177.5(3)
C8 N1 C9 C10 . 92.7(5)
C7 N1 C9 C10 . -87.1(5)
C6 N4 C11 C12 . -148.9(3)
C14 N4 C11 C12 . 51.9(3)
C13 N5 C12 C11 . 54.0(3)
Mn1 N5 C12 C11 2 -179.1(2)
N4 C11 C12 N5 . -52.9(4)
C12 N5 C13 C14 . -55.0(3)
Mn1 N5 C13 C14 2 175.47(16)
C6 N4 C14 C13 . 146.2(3)
C11 N4 C14 C13 . -54.2(3)
N5 C13 C14 N4 . 55.9(3)
