#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:37:24 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179589 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/54/4505481.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_4505481
loop_
_publ_author_name
'Chen, Zhi'
'Gao, Dong-Liang'
'Diao, Chun-Hua'
'Liu, Yue'
'Ren, Jia'
'Chen, Ji'
'Zhao, Bin'
'Shi, Wei'
'Cheng, Peng'
_publ_section_title
;
 Syntheses, Structures Tuned by 4,4′-Bipyridine and Magnetic
 Properties of a Series of Transition Metal Compounds
 Containingo-Carboxylphenoxyacetate Acid
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1201
_journal_paper_doi               10.1021/cg201197k
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C9 H8 Mn O6'
_chemical_formula_weight         267.09
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.737(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.2040(11)
_cell_length_b                   9.634(2)
_cell_length_c                   9.777(2)
_cell_measurement_reflns_used    4887
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      3.92
_cell_volume                     489.95(18)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  SCX-MINI
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4096
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.92
_exptl_absorpt_coefficient_mu    1.357
_exptl_absorpt_correction_T_max  0.7731
_exptl_absorpt_correction_T_min  0.7731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             270
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.223(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1727
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0183
_refine_ls_R_factor_gt           0.0179
_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)+(0.0197P)²+0.0465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0439
_refine_ls_wR_factor_ref         0.0441
_reflns_number_gt                1706
_reflns_number_total             1727
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201197k_si_002.cif
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4505481
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
Mn1 Mn 1.24439(5) 0.37758(3) 0.43979(3) 0.01933(9) Uani 1 1 d .
O1 O 1.1252(3) 0.21889(15) 0.26097(14) 0.0252(3) Uani 1 1 d .
O2 O 0.9259(3) 0.47692(14) 0.35052(15) 0.0261(3) Uani 1 1 d .
O3 O 0.5064(2) 0.47729(15) 0.30382(14) 0.0250(3) Uani 1 1 d .
O4 O 0.9911(3) 0.25904(15) 0.57398(15) 0.0312(4) Uani 1 1 d .
H4A H 0.8494 0.2392 0.5419 0.037 Uiso 1 1 d R
H4B H 1.0556 0.1831 0.5909 0.037 Uiso 1 1 d R
O5 O 1.6091(3) -0.01129(16) 0.38958(15) 0.0323(4) Uani 1 1 d .
O6 O 1.5049(3) 0.20436(14) 0.45125(14) 0.0248(3) Uani 1 1 d .
C1 C 0.7632(4) 0.34079(18) 0.15986(19) 0.0193(5) Uani 1 1 d .
C2 C 0.9544(4) 0.2379(2) 0.1503(2) 0.0206(4) Uani 1 1 d .
C3 C 0.9649(4) 0.1567(2) 0.0322(2) 0.0293(5) Uani 1 1 d .
H3 H 1.0877 0.0870 0.0270 0.035 Uiso 1 1 calc R
C4 C 0.7947(4) 0.1789(3) -0.0770(2) 0.0319(5) Uani 1 1 d .
H4 H 0.8084 0.1263 -0.1562 0.038 Uiso 1 1 calc R
C5 C 0.6034(4) 0.2789(2) -0.0694(2) 0.0317(5) Uani 1 1 d .
H5 H 0.4879 0.2932 -0.1425 0.038 Uiso 1 1 calc R
C6 C 0.5882(4) 0.3570(2) 0.04952(19) 0.0272(5) Uani 1 1 d .
H6 H 0.4573 0.4222 0.0560 0.033 Uiso 1 1 calc R
C7 C 0.7297(4) 0.4362(2) 0.28089(19) 0.0194(4) Uani 1 1 d .
C8 C 1.2787(4) 0.0945(2) 0.2613(2) 0.0291(5) Uani 1 1 d .
H8A H 1.3646 0.0866 0.1750 0.035 Uiso 1 1 calc R
H8B H 1.1682 0.0142 0.2707 0.035 Uiso 1 1 calc R
C9 C 1.4781(4) 0.0968(2) 0.3784(2) 0.0222(4) Uani 1 1 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'
Mn Mn 0.3368 0.7283 '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'
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
O2 Mn1 O5 111.28(6) . 2_856
O2 Mn1 O6 150.54(5) . .
O5 Mn1 O6 98.09(6) 2_856 .
O2 Mn1 O3 92.69(6) . 1_655
O5 Mn1 O3 92.37(6) 2_856 1_655
O6 Mn1 O3 88.20(5) . 1_655
O2 Mn1 O4 90.27(6) . .
O5 Mn1 O4 90.03(6) 2_856 .
O6 Mn1 O4 87.39(6) . .
O3 Mn1 O4 175.23(6) 1_655 .
O2 Mn1 O1 78.56(5) . .
O5 Mn1 O1 169.90(6) 2_856 .
O6 Mn1 O1 72.00(5) . .
O3 Mn1 O1 89.37(5) 1_655 .
O4 Mn1 O1 87.56(5) . .
C2 O1 C8 116.89(15) . .
C2 O1 Mn1 129.08(11) . .
C8 O1 Mn1 113.50(11) . .
C7 O2 Mn1 134.32(13) . .
C7 O3 Mn1 125.15(12) . 1_455
Mn1 O4 H4A 116.3 . .
Mn1 O4 H4B 109.5 . .
H4A O4 H4B 103.2 . .
C9 O5 Mn1 132.68(14) . 2_846
C9 O6 Mn1 123.30(13) . .
C6 C1 C2 118.12(17) . .
C6 C1 C7 116.58(17) . .
C2 C1 C7 125.30(16) . .
O1 C2 C3 121.97(18) . .
O1 C2 C1 118.42(16) . .
C3 C2 C1 119.59(18) . .
C4 C3 C2 120.8(2) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
C3 C4 C5 120.6(2) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C4 C5 C6 118.62(19) . .
C4 C5 H5 120.7 . .
C6 C5 H5 120.7 . .
C5 C6 C1 122.2(2) . .
C5 C6 H6 118.9 . .
C1 C6 H6 118.9 . .
O3 C7 O2 122.71(19) . .
O3 C7 C1 117.45(17) . .
O2 C7 C1 119.75(17) . .
O1 C8 C9 110.82(16) . .
O1 C8 H8A 109.5 . .
C9 C8 H8A 109.5 . .
O1 C8 H8B 109.5 . .
C9 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
O5 C9 O6 125.78(19) . .
O5 C9 C8 114.37(18) . .
O6 C9 C8 119.81(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O2 2.0826(14) .
Mn1 O5 2.1056(15) 2_856
Mn1 O6 2.1507(14) .
Mn1 O3 2.1584(14) 1_655
Mn1 O4 2.2064(15) .
Mn1 O1 2.3902(14) .
O1 C2 1.391(2) .
O1 C8 1.441(2) .
O2 C7 1.272(2) .
O3 C7 1.254(2) .
O3 Mn1 2.1584(14) 1_455
O4 H4A 0.8149 .
O4 H4B 0.8200 .
O5 C9 1.247(2) .
O5 Mn1 2.1056(15) 2_846
O6 C9 1.263(2) .
C1 C6 1.399(3) .
C1 C2 1.410(3) .
C1 C7 1.513(3) .
C2 C3 1.396(3) .
C3 C4 1.383(3) .
C3 H3 0.9300 .
C4 C5 1.389(3) .
C4 H4 0.9300 .
C5 C6 1.390(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C8 C9 1.521(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
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
O2 Mn1 O1 C2 12.54(15) .
O5 Mn1 O1 C2 179.7(3) 2_856
O6 Mn1 O1 C2 -168.65(17) .
O3 Mn1 O1 C2 -80.33(16) 1_655
O4 Mn1 O1 C2 103.31(16) .
O2 Mn1 O1 C8 -176.16(14) .
O5 Mn1 O1 C8 -9.0(4) 2_856
O6 Mn1 O1 C8 2.66(13) .
O3 Mn1 O1 C8 90.97(13) 1_655
O4 Mn1 O1 C8 -85.38(14) .
O5 Mn1 O2 C7 -152.77(18) 2_856
O6 Mn1 O2 C7 22.5(3) .
O3 Mn1 O2 C7 113.63(19) 1_655
O4 Mn1 O2 C7 -62.63(19) .
O1 Mn1 O2 C7 24.82(19) .
O2 Mn1 O6 C9 -4.3(2) .
O5 Mn1 O6 C9 171.28(15) 2_856
O3 Mn1 O6 C9 -96.58(15) 1_655
O4 Mn1 O6 C9 81.62(15) .
O1 Mn1 O6 C9 -6.66(14) .
C8 O1 C2 C3 -12.5(3) .
Mn1 O1 C2 C3 158.59(15) .
C8 O1 C2 C1 166.37(17) .
Mn1 O1 C2 C1 -22.6(2) .
C6 C1 C2 O1 -178.44(17) .
C7 C1 C2 O1 1.3(3) .
C6 C1 C2 C3 0.4(3) .
C7 C1 C2 C3 -179.78(18) .
O1 C2 C3 C4 -179.26(19) .
C1 C2 C3 C4 1.9(3) .
C2 C3 C4 C5 -2.4(3) .
C3 C4 C5 C6 0.6(3) .
C4 C5 C6 C1 1.8(3) .
C2 C1 C6 C5 -2.3(3) .
C7 C1 C6 C5 177.87(19) .
Mn1 O3 C7 O2 -90.7(2) 1_455
Mn1 O3 C7 C1 92.82(18) 1_455
Mn1 O2 C7 O3 134.56(17) .
Mn1 O2 C7 C1 -49.0(3) .
C6 C1 C7 O3 29.8(2) .
C2 C1 C7 O3 -149.96(18) .
C6 C1 C7 O2 -146.78(18) .
C2 C1 C7 O2 33.4(3) .
C2 O1 C8 C9 172.91(16) .
Mn1 O1 C8 C9 0.5(2) .
Mn1 O5 C9 O6 40.0(3) 2_846
Mn1 O5 C9 C8 -142.48(17) 2_846
Mn1 O6 C9 O5 -173.02(15) .
Mn1 O6 C9 C8 9.5(2) .
O1 C8 C9 O5 176.27(17) .
O1 C8 C9 O6 -6.0(3) .
