#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:10:05 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179778 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/74/7007488.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_7007488
loop_
_publ_author_name
'Chen, Chun-Long'
'Ellsworth, Joseph M.'
'Goforth, Andrea M.'
'Smith, Mark D.'
'Su, Cheng-Yong'
'Zur Loye, Hans-Conrad'
_publ_section_title
;
 A new 2-carboxylate-substituted 4,4'-bipyridine ligand: coordination
 chemistry of 4,4'-bipyridine-2-carboxylic acid and its synthetic
 intermediate 2-methyl-4,4'-bipyridine.
;
_journal_issue                   44
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5278
_journal_page_last               5286
_journal_paper_doi               10.1039/b606280f
_journal_year                    2006
_chemical_formula_moiety         'C22 H18 Mn N4 O6, 2(H2 O)'
_chemical_formula_sum            'C22 H22 Mn N4 O8'
_chemical_formula_weight         525.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.3050(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.3775(10)
_cell_length_b                   7.6358(4)
_cell_length_c                   15.1202(7)
_cell_measurement_reflns_used    7099
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      26.357
_cell_measurement_theta_min      2.698
_cell_volume                     2233.50(19)
_computing_cell_refinement       'SAINT+ NT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART NT V5.625 (Bruker, 1998)'
_computing_data_reduction        'SAINT+ NT V6.22'
_computing_molecular_graphics    'SHELXTL V6.1 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       '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  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11586
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2292
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0344
_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)+(0.0493P)²+0.6720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                2060
_reflns_number_total             2292
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b606280f.txt
_cod_data_source_block           mn44coot
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               7007488
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.2500 0.30503(5) 0.5000 0.02257(13) Uani 1 2 d S . .
C1 C 0.33547(9) 0.2023(2) 0.34549(11) 0.0218(4) Uani 1 1 d . . .
C2 C 0.38400(9) 0.2037(2) 0.28171(11) 0.0228(4) Uani 1 1 d . . .
H2 H 0.3739 0.1503 0.2257 0.023(5) Uiso 1 1 calc R . .
C3 C 0.44748(9) 0.2838(2) 0.30041(11) 0.0237(4) Uani 1 1 d . . .
C4 C 0.45928(9) 0.3619(2) 0.38295(12) 0.0289(4) Uani 1 1 d . . .
H4 H 0.5026 0.4147 0.3989 0.037(5) Uiso 1 1 calc R . .
C5 C 0.40714(9) 0.3618(2) 0.44150(12) 0.0294(4) Uani 1 1 d . . .
H5 H 0.4149 0.4202 0.4967 0.030(5) Uiso 1 1 calc R . .
C6 C 0.26701(9) 0.1064(2) 0.33154(11) 0.0224(4) Uani 1 1 d . . .
C7 C 0.61837(10) 0.2534(2) 0.19476(13) 0.0298(4) Uani 1 1 d . . .
H7 H 0.6648 0.2236 0.2118 0.024(5) Uiso 1 1 calc R . .
C8 C 0.56977(9) 0.2485(2) 0.25852(12) 0.0279(4) Uani 1 1 d . . .
H8 H 0.5831 0.2188 0.3181 0.027(5) Uiso 1 1 calc R . .
C9 C 0.50127(9) 0.2876(2) 0.23419(12) 0.0245(4) Uani 1 1 d . . .
C10 C 0.48433(10) 0.3306(2) 0.14632(12) 0.0283(4) Uani 1 1 d . . .
H10 H 0.4380 0.3560 0.1267 0.024(5) Uiso 1 1 calc R . .
C11 C 0.53710(10) 0.3353(2) 0.08795(13) 0.0314(4) Uani 1 1 d . . .
H11 H 0.5255 0.3670 0.0282 0.036(5) Uiso 1 1 calc R . .
N1 N 0.34627(8) 0.28326(18) 0.42410(9) 0.0237(3) Uani 1 1 d . . .
N2 N 0.60304(8) 0.2980(2) 0.11059(11) 0.0312(4) Uani 1 1 d . . .
O1 O 0.22685(6) 0.11722(16) 0.39515(8) 0.0268(3) Uani 1 1 d . . .
O2 O 0.25509(6) 0.02407(16) 0.26193(7) 0.0269(3) Uani 1 1 d . . .
O3 O 0.20491(8) 0.49890(18) 0.40918(9) 0.0345(3) Uani 1 1 d D . .
H3A H 0.1984(15) 0.600(2) 0.4227(18) 0.070(9) Uiso 1 1 d D . .
H3B H 0.2153(11) 0.499(3) 0.3590(10) 0.041(6) Uiso 1 1 d D . .
O4 O 0.15948(7) 0.81736(17) 0.44599(10) 0.0328(3) Uani 1 1 d D . .
H4A H 0.1805(11) 0.904(2) 0.4332(15) 0.049(7) Uiso 1 1 d D . .
H4B H 0.1562(14) 0.824(3) 0.4987(10) 0.057(8) Uiso 1 1 d D . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 97.05(7) . 2_556 ?
O1 Mn1 O3 85.96(5) . . ?
O1 Mn1 O3 167.06(5) 2_556 . ?
O1 Mn1 O3 167.07(5) . 2_556 ?
O1 Mn1 O3 85.96(5) 2_556 2_556 ?
O3 Mn1 O3 93.90(8) . 2_556 ?
O1 Mn1 N1 100.46(5) . 2_556 ?
O1 Mn1 N1 73.78(5) 2_556 2_556 ?
O3 Mn1 N1 93.31(5) . 2_556 ?
O3 Mn1 N1 92.46(5) 2_556 2_556 ?
O1 Mn1 N1 73.78(5) . . ?
O1 Mn1 N1 100.46(5) 2_556 . ?
O3 Mn1 N1 92.47(5) . . ?
O3 Mn1 N1 93.31(5) 2_556 . ?
N1 Mn1 N1 171.53(7) 2_556 . ?
N1 C1 C2 122.31(16) . . ?
N1 C1 C6 115.73(14) . . ?
C2 C1 C6 121.96(15) . . ?
C1 C2 C3 119.39(16) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 118.02(16) . . ?
C2 C3 C9 121.26(15) . . ?
C4 C3 C9 120.72(16) . . ?
C5 C4 C3 119.12(16) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 122.97(16) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O2 C6 O1 125.69(16) . . ?
O2 C6 C1 118.82(14) . . ?
O1 C6 C1 115.48(14) . . ?
N2 C7 C8 123.18(17) . . ?
N2 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.15(17) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 118.25(16) . . ?
C8 C9 C3 120.92(16) . . ?
C10 C9 C3 120.83(16) . . ?
C11 C10 C9 118.15(17) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
N2 C11 C10 124.09(18) . . ?
N2 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
C5 N1 C1 118.08(14) . . ?
C5 N1 Mn1 127.91(11) . . ?
C1 N1 Mn1 113.14(11) . . ?
C7 N2 C11 117.16(16) . . ?
C6 O1 Mn1 119.07(11) . . ?
Mn1 O3 H3A 124(2) . . ?
Mn1 O3 H3B 119.2(16) . . ?
H3A O3 H3B 107(2) . . ?
H4A O4 H4B 105(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.1654(12) . ?
Mn1 O1 2.1655(12) 2_556 ?
Mn1 O3 2.1684(14) . ?
Mn1 O3 2.1684(14) 2_556 ?
Mn1 N1 2.2520(14) 2_556 ?
Mn1 N1 2.2520(14) . ?
C1 N1 1.345(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.520(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 C9 1.487(2) . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.336(2) . ?
C5 H5 0.9500 . ?
C6 O2 1.236(2) . ?
C6 O1 1.274(2) . ?
C7 N2 1.334(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 N2 1.334(3) . ?
C11 H11 0.9500 . ?
O3 H3A 0.809(14) . ?
O3 H3B 0.796(13) . ?
O4 H4A 0.808(14) . ?
O4 H4B 0.805(14) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O4 0.809(14) 1.866(16) 2.6560(19) 165(3) .
O3 H3B O2 0.796(13) 1.956(14) 2.7490(18) 174(2) 7
O4 H4A O1 0.808(14) 1.960(14) 2.7665(18) 176(2) 1_565
O4 H4B N2 0.805(14) 2.041(17) 2.780(2) 152(3) 3_455
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 3.1(2) . . . . ?
C6 C1 C2 C3 -175.77(15) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C1 C2 C3 C9 179.66(15) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C9 C3 C4 C5 177.50(16) . . . . ?
C3 C4 C5 N1 2.9(3) . . . . ?
N1 C1 C6 O2 -177.40(14) . . . . ?
C2 C1 C6 O2 1.6(2) . . . . ?
N1 C1 C6 O1 1.7(2) . . . . ?
C2 C1 C6 O1 -179.32(15) . . . . ?
N2 C7 C8 C9 1.6(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C3 179.97(16) . . . . ?
C2 C3 C9 C8 -134.57(18) . . . . ?
C4 C3 C9 C8 45.9(2) . . . . ?
C2 C3 C9 C10 45.5(2) . . . . ?
C4 C3 C9 C10 -133.99(19) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C3 C9 C10 C11 178.73(16) . . . . ?
C9 C10 C11 N2 1.2(3) . . . . ?
C4 C5 N1 C1 -0.6(3) . . . . ?
C4 C5 N1 Mn1 -169.23(14) . . . . ?
C2 C1 N1 C5 -2.4(2) . . . . ?
C6 C1 N1 C5 176.56(15) . . . . ?
C2 C1 N1 Mn1 167.82(12) . . . . ?
C6 C1 N1 Mn1 -13.20(17) . . . . ?
O1 Mn1 N1 C5 -176.84(16) . . . . ?
O1 Mn1 N1 C5 -82.46(15) 2_556 . . . ?
O3 Mn1 N1 C5 98.09(15) . . . . ?
O3 Mn1 N1 C5 4.04(15) 2_556 . . . ?
O1 Mn1 N1 C1 14.09(11) . . . . ?
O1 Mn1 N1 C1 108.47(11) 2_556 . . . ?
O3 Mn1 N1 C1 -70.98(12) . . . . ?
O3 Mn1 N1 C1 -165.03(11) 2_556 . . . ?
C8 C7 N2 C11 -1.5(3) . . . . ?
C10 C11 N2 C7 0.1(3) . . . . ?
O2 C6 O1 Mn1 -169.17(13) . . . . ?
C1 C6 O1 Mn1 11.81(18) . . . . ?
O1 Mn1 O1 C6 -113.09(13) 2_556 . . . ?
O3 Mn1 O1 C6 79.56(12) . . . . ?
O3 Mn1 O1 C6 -10.3(3) 2_556 . . . ?
N1 Mn1 O1 C6 172.18(12) 2_556 . . . ?
N1 Mn1 O1 C6 -14.20(12) . . . . ?
