#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/70/2237025.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_2237025
loop_
_publ_author_name
'Hwang, In Hong'
'Kim, Pan-Gi'
'Lee, Jae-Cheon'
'Kim, Cheal'
'Kim, Youngmee'
_publ_section_title
;
 Bis(μ-2-carboxymethyl-2-hydroxybutanedioato)bis[diaquamanganese(II)]--1,2-bis(pyridin-4-yl)ethene--water
 (1/1/2)
;
_journal_coeditor_code           SJ5281
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1516
_journal_page_last               m1517
_journal_paper_doi               10.1107/S1600536812047034
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac
'[Mn2 (C6 H6 O7)2 (H2 O)4], C12 H10 N2, 2H2 O'
_chemical_formula_moiety         'C12 H20 Mn2 O18, C12 H10 N2, 2(H2 O)'
_chemical_formula_sum            'C24 H34 Mn2 N2 O20'
_chemical_formula_weight         780.41
_chemical_name_systematic
;
Bis(μ-2-carboxymethyl-2-hydroxybutanedioato)bis[diaquamanganese(II)]--
1,2-bis(pyridin-4-yl)ethene--water (1/1/2)
;
_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           SHELXTL
_cell_angle_alpha                70.24(3)
_cell_angle_beta                 67.11(3)
_cell_angle_gamma                75.52(3)
_cell_formula_units_Z            1
_cell_length_a                   9.3970(19)
_cell_length_b                   9.4580(19)
_cell_length_c                   10.131(2)
_cell_measurement_reflns_used    11909
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.7
_cell_volume                     773.3(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_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      170(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and 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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4358
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.8758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.632
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0381
_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)+(0.0538P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                2423
_reflns_number_total             2973
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5281.cif
_cod_data_source_block           I
_cod_database_code               2237025
_cod_database_fobs_code          2237025
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_symmetry_multiplicity
Mn Mn1 0.59596(4) 0.68914(4) 0.60932(4) 0.01775(14) Uani d . 1 1
O O1 0.4231(2) 0.51640(19) 0.72246(19) 0.0179(4) Uani d D 1 1
H H1O 0.435(3) 0.479(3) 0.652(2) 0.021 Uiso d D 1 1
O O2 0.3899(2) 0.79755(19) 0.54416(19) 0.0226(4) Uani d . 1 1
O O3 0.1299(2) 0.8203(2) 0.6391(2) 0.0306(5) Uani d . 1 1
O O4 0.4605(2) 0.7549(2) 0.81346(19) 0.0248(4) Uani d . 1 1
O O5 0.3362(2) 0.6926(2) 1.0561(2) 0.0289(5) Uani d D 1 1
H H5O 0.411(2) 0.731(3) 1.055(3) 0.035 Uiso d D 1 1
O O6 0.3225(2) 0.4206(2) 0.56485(19) 0.0232(4) Uani d . 1 1
O O7 0.0686(2) 0.4237(2) 0.6196(2) 0.0335(5) Uani d . 1 1
O O8 0.7614(2) 0.5543(2) 0.7192(2) 0.0263(4) Uani d D 1 1
H H8A 0.8656(9) 0.526(3) 0.669(3) 0.032 Uiso d D 1 1
H H8B 0.736(3) 0.4655(17) 0.794(2) 0.032 Uiso d D 1 1
O O9 0.7071(2) 0.8889(2) 0.5139(2) 0.0311(5) Uani d D 1 1
H H9A 0.8153(4) 0.881(3) 0.478(3) 0.037 Uiso d D 1 1
H H9B 0.671(3) 0.9920(8) 0.501(3) 0.037 Uiso d D 1 1
C C1 0.2687(3) 0.6001(3) 0.7591(3) 0.0166(5) Uani d . 1 1
C C2 0.2613(3) 0.7522(3) 0.6372(3) 0.0187(5) Uani d . 1 1
C C3 0.2331(3) 0.6280(3) 0.9100(3) 0.0209(6) Uani d . 1 1
H H3A 0.1328 0.6957 0.9320 0.025 Uiso calc R 1 1
H H3B 0.2183 0.5299 0.9871 0.025 Uiso calc R 1 1
C C4 0.3533(3) 0.6963(3) 0.9249(3) 0.0195(5) Uani d . 1 1
C C5 0.1477(3) 0.5074(3) 0.7752(3) 0.0184(5) Uani d . 1 1
H H5A 0.1411 0.4199 0.8642 0.022 Uiso calc R 1 1
H H5B 0.0447 0.5713 0.7934 0.022 Uiso calc R 1 1
C C6 0.1791(3) 0.4481(3) 0.6430(3) 0.0188(5) Uani d . 1 1
N N11 0.5629(3) 0.8142(2) 0.0477(2) 0.0236(5) Uani d . 1 1
C C14 0.6748(3) 0.8996(3) 0.1754(3) 0.0234(6) Uani d . 1 1
H H14 0.6673 0.9197 0.2638 0.028 Uiso calc R 1 1
C C11 0.6896(3) 0.8400(3) -0.0763(3) 0.0257(6) Uani d . 1 1
H H11 0.6931 0.8193 -0.1630 0.031 Uiso calc R 1 1
C C12 0.8134(3) 0.8954(3) -0.0799(3) 0.0247(6) Uani d . 1 1
H H12 0.9015 0.9128 -0.1679 0.030 Uiso calc R 1 1
C C13 0.8076(3) 0.9261(3) 0.0493(3) 0.0216(6) Uani d . 1 1
C C15 0.5544(3) 0.8440(3) 0.1713(3) 0.0244(6) Uani d . 1 1
H H15 0.4641 0.8267 0.2572 0.029 Uiso calc R 1 1
C C16 0.9369(3) 0.9793(3) 0.0573(3) 0.0246(6) Uani d . 1 1
H H16 0.9299 0.9845 0.1517 0.030 Uiso calc R 1 1
O O1W 0.0209(3) 0.8324(2) 0.4096(3) 0.0387(5) Uani d D 1 1
H H1WA 0.030(4) 0.7316(11) 0.412(4) 0.046 Uiso d D 1 1
H H1WB 0.063(4) 0.826(4) 0.481(3) 0.046 Uiso d D 1 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
O9 Mn1 O6 . 2_666 104.69(8)
O9 Mn1 O8 . . 95.79(8)
O6 Mn1 O8 2_666 . 95.74(7)
O9 Mn1 O4 . . 91.93(8)
O6 Mn1 O4 2_666 . 162.66(7)
O8 Mn1 O4 . . 87.30(8)
O9 Mn1 O2 . . 94.80(8)
O6 Mn1 O2 2_666 . 89.16(7)
O8 Mn1 O2 . . 166.80(7)
O4 Mn1 O2 . . 84.48(7)
O9 Mn1 O1 . . 166.09(7)
O6 Mn1 O1 2_666 . 83.34(7)
O8 Mn1 O1 . . 94.66(7)
O4 Mn1 O1 . . 79.39(7)
O2 Mn1 O1 . . 73.70(7)
C1 O1 Mn1 . . 107.29(13)
C1 O1 H1O . . 107.4(18)
Mn1 O1 H1O . . 103.0(18)
C2 O2 Mn1 . . 115.41(15)
C4 O4 Mn1 . . 130.73(16)
C4 O5 H5O . . 109(2)
C6 O6 Mn1 . 2_666 124.98(16)
Mn1 O8 H8A . . 123.5(18)
Mn1 O8 H8B . . 120.1(18)
H8A O8 H8B . . 102(2)
Mn1 O9 H9A . . 120.1(18)
Mn1 O9 H9B . . 134.0(19)
H9A O9 H9B . . 106(3)
O1 C1 C5 . . 110.87(18)
O1 C1 C3 . . 106.59(19)
C5 C1 C3 . . 108.3(2)
O1 C1 C2 . . 110.49(19)
C5 C1 C2 . . 109.4(2)
C3 C1 C2 . . 111.13(19)
O3 C2 O2 . . 125.2(2)
O3 C2 C1 . . 116.8(2)
O2 C2 C1 . . 118.0(2)
C4 C3 C1 . . 116.8(2)
C4 C3 H3A . . 108.1
C1 C3 H3A . . 108.1
C4 C3 H3B . . 108.1
C1 C3 H3B . . 108.1
H3A C3 H3B . . 107.3
O4 C4 O5 . . 122.9(2)
O4 C4 C3 . . 121.5(2)
O5 C4 C3 . . 115.6(2)
C6 C5 C1 . . 115.7(2)
C6 C5 H5A . . 108.4
C1 C5 H5A . . 108.4
C6 C5 H5B . . 108.4
C1 C5 H5B . . 108.4
H5A C5 H5B . . 107.4
O7 C6 O6 . . 123.8(2)
O7 C6 C5 . . 119.6(2)
O6 C6 C5 . . 116.5(2)
C15 N11 C11 . . 120.3(2)
C15 C14 C13 . . 119.9(2)
C15 C14 H14 . . 120.1
C13 C14 H14 . . 120.1
N11 C11 C12 . . 121.7(2)
N11 C11 H11 . . 119.2
C12 C11 H11 . . 119.2
C11 C12 C13 . . 119.0(3)
C11 C12 H12 . . 120.5
C13 C12 H12 . . 120.5
C14 C13 C12 . . 118.2(2)
C14 C13 C16 . . 119.2(2)
C12 C13 C16 . . 122.6(2)
N11 C15 C14 . . 121.0(3)
N11 C15 H15 . . 119.5
C14 C15 H15 . . 119.5
C16 C16 C13 2_775 . 124.9(3)
C16 C16 H16 2_775 . 117.5
C13 C16 H16 . . 117.5
H1WA O1W H1WB . . 103(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Mn1 O9 . 2.136(2)
Mn1 O6 2_666 2.1373(18)
Mn1 O8 . 2.163(2)
Mn1 O4 . 2.1701(19)
Mn1 O2 . 2.1864(19)
Mn1 O1 . 2.288(2)
O1 C1 . 1.440(3)
O1 H1O . 0.860(2)
O2 C2 . 1.278(3)
O3 C2 . 1.238(3)
O4 C4 . 1.252(3)
O5 C4 . 1.264(3)
O5 H5O . 0.861(2)
O6 C6 . 1.282(3)
O6 Mn1 2_666 2.1372(18)
O7 C6 . 1.239(3)
O8 H8A . 0.929(2)
O8 H8B . 0.930(2)
O9 H9A . 0.930(2)
O9 H9B . 0.930(2)
C1 C5 . 1.532(3)
C1 C3 . 1.533(3)
C1 C2 . 1.554(3)
C3 C4 . 1.510(3)
C3 H3A . 0.9900
C3 H3B . 0.9900
C5 C6 . 1.521(3)
C5 H5A . 0.9900
C5 H5B . 0.9900
N11 C15 . 1.342(3)
N11 C11 . 1.352(4)
C14 C15 . 1.381(4)
C14 C13 . 1.397(4)
C14 H14 . 0.9500
C11 C12 . 1.373(4)
C11 H11 . 0.9500
C12 C13 . 1.412(4)
C12 H12 . 0.9500
C13 C16 . 1.465(4)
C15 H15 . 0.9500
C16 C16 2_775 1.328(5)
C16 H16 . 0.9500
O1W H1WA . 0.930(2)
O1W H1WB . 0.930(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
C12 H12 O3 1_654 0.95 2.48 3.344(4) 151.3
C11 H11 O4 1_554 0.95 2.53 3.143(3) 122.8
O9 H9B O3 2_676 0.930(2) 2.56(3) 3.113(3) 118(2)
O9 H9B O2 2_676 0.930(2) 1.876(4) 2.803(3) 175(3)
O9 H9A O1W 1_655 0.930(2) 1.776(6) 2.695(3) 170(3)
O8 H8B O5 2_667 0.930(2) 1.782(5) 2.707(3) 173(3)
O8 H8A O7 1_655 0.929(2) 1.868(9) 2.769(3) 163(3)
O5 H5O N11 1_556 0.861(2) 1.764(4) 2.625(3) 178(3)
O1W H1WB O3 . 0.930(2) 1.916(5) 2.843(3) 175(3)
O1 H1O O6 . 0.860(2) 1.880(17) 2.616(2) 143(2)
O1W H1WA O7 2_566 0.930(2) 2.082(19) 2.891(3) 145(3)
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_4
_geom_torsion
O9 Mn1 O1 C1 . . 1.5(4)
O6 Mn1 O1 C1 2_666 . -124.70(14)
O8 Mn1 O1 C1 . . 140.04(14)
O4 Mn1 O1 C1 . . 53.67(14)
O2 Mn1 O1 C1 . . -33.63(13)
O9 Mn1 O2 C2 . . -144.09(17)
O6 Mn1 O2 C2 2_666 . 111.24(17)
O8 Mn1 O2 C2 . . -0.8(4)
O4 Mn1 O2 C2 . . -52.61(17)
O1 Mn1 O2 C2 . . 27.93(16)
O9 Mn1 O4 C4 . . 173.5(2)
O6 Mn1 O4 C4 2_666 . 9.9(4)
O8 Mn1 O4 C4 . . -90.8(2)
O2 Mn1 O4 C4 . . 78.9(2)
O1 Mn1 O4 C4 . . 4.5(2)
Mn1 O1 C1 C5 . . 156.94(15)
Mn1 O1 C1 C3 . . -85.35(18)
Mn1 O1 C1 C2 . . 35.5(2)
Mn1 O2 C2 O3 . . 162.7(2)
Mn1 O2 C2 C1 . . -16.8(3)
O1 C1 C2 O3 . . 165.9(2)
C5 C1 C2 O3 . . 43.6(3)
C3 C1 C2 O3 . . -76.0(3)
O1 C1 C2 O2 . . -14.6(3)
C5 C1 C2 O2 . . -136.9(2)
C3 C1 C2 O2 . . 103.5(2)
O1 C1 C3 C4 . . 51.3(3)
C5 C1 C3 C4 . . 170.7(2)
C2 C1 C3 C4 . . -69.1(3)
Mn1 O4 C4 O5 . . 144.1(2)
Mn1 O4 C4 C3 . . -37.3(3)
C1 C3 C4 O4 . . 13.8(4)
C1 C3 C4 O5 . . -167.5(2)
O1 C1 C5 C6 . . -54.3(3)
C3 C1 C5 C6 . . -171.0(2)
C2 C1 C5 C6 . . 67.8(3)
Mn1 O6 C6 O7 2_666 . -5.4(4)
Mn1 O6 C6 C5 2_666 . 171.83(15)
C1 C5 C6 O7 . . -153.2(2)
C1 C5 C6 O6 . . 29.4(3)
C15 N11 C11 C12 . . 0.7(4)
N11 C11 C12 C13 . . -0.1(4)
C15 C14 C13 C12 . . 0.3(4)
C15 C14 C13 C16 . . -177.6(2)
C11 C12 C13 C14 . . -0.4(4)
C11 C12 C13 C16 . . 177.4(2)
C11 N11 C15 C14 . . -0.8(4)
C13 C14 C15 N11 . . 0.3(4)
C14 C13 C16 C16 . 2_775 -174.0(3)
C12 C13 C16 C16 . 2_775 8.2(5)
