#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/33/8103340.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_8103340
loop_
_publ_author_name
'Xiao-Ling Li'
'Ke-Qiang Wang'
_publ_section_title
;
 Crystal structure of
 bis{aqua[m-2-(2-carboxylatophenyl)acetato-k3O1:O3,O4](1,10-phenanthroline-k2N,N')manganese(II)},
 [Mn(C9H6O4)(C12H8N2)(H2O)]2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              135
_journal_volume                  227
_journal_year                    2012
_chemical_formula_sum            'C21 H16 Mn N2 O5'
_chemical_formula_weight         431.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.992(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9125(13)
_cell_length_b                   19.290(3)
_cell_length_c                   11.1500(16)
_cell_measurement_reflns_used    2355
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.45
_cell_measurement_theta_min      2.75
_cell_volume                     1898.3(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14239
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.8981
_exptl_absorpt_correction_T_min  0.7995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0398
_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)+(0.0396P)²+0.5157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                2420
_reflns_number_total             3538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3683.cff
_cod_data_source_block           a
_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_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8103340
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Mn1 Mn 0.73898(5) 0.04525(2) 0.17018(3) 0.04096(15) Uani 1 1 d .
O1 O 0.8339(2) 0.13475(10) 0.10376(16) 0.0490(5) Uani 1 1 d .
O2 O 0.6487(2) 0.17532(12) -0.0321(2) 0.0661(6) Uani 1 1 d .
O3 O 1.0808(2) 0.03151(10) -0.13090(17) 0.0508(5) Uani 1 1 d .
O4 O 1.2920(2) 0.02347(10) -0.00586(17) 0.0496(5) Uani 1 1 d .
O5 O 0.5218(2) 0.09268(10) 0.11694(16) 0.0497(5) Uani 1 1 d .
H1W H 0.5301 0.1249 0.0663 0.075 Uiso 1 1 d R
H2W H 0.4478 0.0680 0.0852 0.075 Uiso 1 1 d R
N1 N 0.8318(3) 0.07355(12) 0.36079(19) 0.0446(6) Uani 1 1 d .
N2 N 0.6407(3) -0.03216(12) 0.28995(19) 0.0470(6) Uani 1 1 d .
C1 C 0.9251(3) 0.12584(16) 0.3946(3) 0.0539(8) Uani 1 1 d .
H1 H 0.9556 0.1543 0.3352 0.065 Uiso 1 1 calc R
C2 C 0.9791(4) 0.13990(17) 0.5156(3) 0.0609(9) Uani 1 1 d .
H2 H 1.0442 0.1770 0.5362 0.073 Uiso 1 1 calc R
C3 C 0.9351(4) 0.09844(17) 0.6031(3) 0.0574(8) Uani 1 1 d .
H3 H 0.9709 0.1071 0.6841 0.069 Uiso 1 1 calc R
C4 C 0.8368(3) 0.04306(15) 0.5721(2) 0.0473(7) Uani 1 1 d .
C5 C 0.7825(4) -0.00223(17) 0.6586(3) 0.0599(9) Uani 1 1 d .
H5A H 0.8154 0.0042 0.7407 0.072 Uiso 1 1 calc R
C6 C 0.6851(4) -0.05355(16) 0.6232(3) 0.0578(8) Uani 1 1 d .
H6 H 0.6497 -0.0812 0.6816 0.069 Uiso 1 1 calc R
C7 C 0.6343(3) -0.06702(15) 0.4979(3) 0.0489(7) Uani 1 1 d .
C8 C 0.5339(4) -0.12040(16) 0.4558(3) 0.0594(9) Uani 1 1 d .
H8 H 0.4967 -0.1499 0.5107 0.071 Uiso 1 1 calc R
C9 C 0.4908(4) -0.12908(17) 0.3348(3) 0.0645(9) Uani 1 1 d .
H9 H 0.4258 -0.1649 0.3061 0.077 Uiso 1 1 calc R
C10 C 0.5458(4) -0.08333(16) 0.2547(3) 0.0581(8) Uani 1 1 d .
H10 H 0.5143 -0.0890 0.1723 0.070 Uiso 1 1 calc R
C11 C 0.6850(3) -0.02374(14) 0.4108(2) 0.0422(7) Uani 1 1 d .
C12 C 0.7875(3) 0.03208(14) 0.4482(2) 0.0418(7) Uani 1 1 d .
C13 C 0.9012(3) 0.19177(13) -0.0716(2) 0.0387(6) Uani 1 1 d .
C14 C 1.0533(3) 0.17268(14) -0.0569(2) 0.0433(7) Uani 1 1 d .
C15 C 1.1476(4) 0.20471(16) -0.1307(3) 0.0595(9) Uani 1 1 d .
H15 H 1.2500 0.1933 -0.1202 0.071 Uiso 1 1 calc R
C16 C 1.0948(5) 0.25231(17) -0.2180(3) 0.0679(10) Uani 1 1 d .
H16 H 1.1607 0.2729 -0.2652 0.082 Uiso 1 1 calc R
C17 C 0.9434(4) 0.26922(16) -0.2349(3) 0.0621(9) Uani 1 1 d .
H17 H 0.9053 0.3003 -0.2954 0.074 Uiso 1 1 calc R
C18 C 0.8490(4) 0.23991(14) -0.1618(3) 0.0518(8) Uani 1 1 d .
H18 H 0.7473 0.2524 -0.1724 0.062 Uiso 1 1 calc R
C19 C 0.7857(3) 0.16512(14) 0.0043(3) 0.0439(7) Uani 1 1 d .
C20 C 1.1246(3) 0.11639(15) 0.0271(2) 0.0484(7) Uani 1 1 d .
H20A H 1.2147 0.1347 0.0757 0.058 Uiso 1 1 calc R
H20B H 1.0540 0.1028 0.0816 0.058 Uiso 1 1 calc R
C21 C 1.1669(3) 0.05366(14) -0.0410(2) 0.0402(7) 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'
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
O1 Mn1 O5 86.80(7) . .
O1 Mn1 N1 91.17(8) . .
O5 Mn1 N1 111.00(8) . .
O1 Mn1 O4 101.94(7) . 3_755
O5 Mn1 O4 91.27(7) . 3_755
N1 Mn1 O4 154.86(8) . 3_755
O1 Mn1 N2 163.54(8) . .
O5 Mn1 N2 92.09(8) . .
N1 Mn1 N2 73.89(8) . .
O4 Mn1 N2 94.49(8) 3_755 .
O1 Mn1 O3 97.89(7) . 3_755
O5 Mn1 O3 149.13(7) . 3_755
N1 Mn1 O3 99.44(8) . 3_755
O4 Mn1 O3 57.88(7) 3_755 3_755
N2 Mn1 O3 91.48(8) . 3_755
O1 Mn1 C21 103.35(8) . 3_755
O5 Mn1 C21 120.48(8) . 3_755
N1 Mn1 C21 126.87(9) . 3_755
O4 Mn1 C21 29.26(7) 3_755 3_755
N2 Mn1 C21 91.36(8) . 3_755
O3 Mn1 C21 28.75(7) 3_755 3_755
C19 O1 Mn1 125.47(18) . .
C21 O3 Mn1 90.30(16) . 3_755
C21 O4 Mn1 90.90(16) . 3_755
Mn1 O5 H1W 109.7 . .
Mn1 O5 H2W 119.6 . .
H1W O5 H2W 105.5 . .
C1 N1 C12 118.4(2) . .
C1 N1 Mn1 126.10(19) . .
C12 N1 Mn1 115.52(18) . .
C10 N2 C11 117.9(2) . .
C10 N2 Mn1 126.99(19) . .
C11 N2 Mn1 115.07(18) . .
N1 C1 C2 122.7(3) . .
N1 C1 H1 118.6 . .
C2 C1 H1 118.6 . .
C3 C2 C1 118.9(3) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C2 C3 C4 120.4(3) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C3 C4 C12 117.3(3) . .
C3 C4 C5 124.1(3) . .
C12 C4 C5 118.7(3) . .
C6 C5 C4 121.2(3) . .
C6 C5 H5A 119.4 . .
C4 C5 H5A 119.4 . .
C5 C6 C7 121.7(3) . .
C5 C6 H6 119.1 . .
C7 C6 H6 119.1 . .
C8 C7 C11 117.3(3) . .
C8 C7 C6 124.1(3) . .
C11 C7 C6 118.6(3) . .
C9 C8 C7 120.1(3) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
C8 C9 C10 118.8(3) . .
C8 C9 H9 120.6 . .
C10 C9 H9 120.6 . .
N2 C10 C9 123.4(3) . .
N2 C10 H10 118.3 . .
C9 C10 H10 118.3 . .
N2 C11 C7 122.5(3) . .
N2 C11 C12 117.6(2) . .
C7 C11 C12 119.9(3) . .
N1 C12 C4 122.2(3) . .
N1 C12 C11 117.9(2) . .
C4 C12 C11 119.9(2) . .
C14 C13 C18 118.8(3) . .
C14 C13 C19 124.9(2) . .
C18 C13 C19 116.3(3) . .
C13 C14 C15 117.9(3) . .
C13 C14 C20 125.5(3) . .
C15 C14 C20 116.4(3) . .
C16 C15 C14 122.5(3) . .
C16 C15 H15 118.7 . .
C14 C15 H15 118.7 . .
C15 C16 C17 119.3(3) . .
C15 C16 H16 120.4 . .
C17 C16 H16 120.4 . .
C18 C17 C16 119.5(3) . .
C18 C17 H17 120.3 . .
C16 C17 H17 120.3 . .
C17 C18 C13 122.0(3) . .
C17 C18 H18 119.0 . .
C13 C18 H18 119.0 . .
O2 C19 O1 123.5(3) . .
O2 C19 C13 118.4(3) . .
O1 C19 C13 118.0(3) . .
C21 C20 C14 112.2(2) . .
C21 C20 H20A 109.2 . .
C14 C20 H20A 109.2 . .
C21 C20 H20B 109.2 . .
C14 C20 H20B 109.2 . .
H20A C20 H20B 107.9 . .
O3 C21 O4 120.4(3) . .
O3 C21 C20 120.7(2) . .
O4 C21 C20 118.9(2) . .
O3 C21 Mn1 60.95(14) . 3_755
O4 C21 Mn1 59.85(14) . 3_755
C20 C21 Mn1 173.33(19) . 3_755
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O1 2.1022(19) .
Mn1 O5 2.1485(19) .
Mn1 N1 2.238(2) .
Mn1 O4 2.2472(19) 3_755
Mn1 N2 2.259(2) .
Mn1 O3 2.272(2) 3_755
Mn1 C21 2.599(3) 3_755
O1 C19 1.275(3) .
O2 C19 1.248(3) .
O3 C21 1.250(3) .
O3 Mn1 2.272(2) 3_755
O4 C21 1.270(3) .
O4 Mn1 2.2472(19) 3_755
O5 H1W 0.8500 .
O5 H2W 0.8499 .
N1 C1 1.328(3) .
N1 C12 1.361(3) .
N2 C10 1.323(4) .
N2 C11 1.360(3) .
C1 C2 1.394(4) .
C1 H1 0.9300 .
C2 C3 1.361(4) .
C2 H2 0.9300 .
C3 C4 1.394(4) .
C3 H3 0.9300 .
C4 C12 1.407(4) .
C4 C5 1.434(4) .
C5 C6 1.339(4) .
C5 H5A 0.9300 .
C6 C7 1.432(4) .
C6 H6 0.9300 .
C7 C8 1.401(4) .
C7 C11 1.402(4) .
C8 C9 1.361(4) .
C8 H8 0.9300 .
C9 C10 1.392(4) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 C12 1.436(4) .
C13 C14 1.392(4) .
C13 C18 1.400(4) .
C13 C19 1.511(4) .
C14 C15 1.399(4) .
C14 C20 1.514(4) .
C15 C16 1.373(4) .
C15 H15 0.9300 .
C16 C17 1.376(5) .
C16 H16 0.9300 .
C17 C18 1.372(4) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C20 C21 1.504(4) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 Mn1 2.599(3) 3_755
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
O5 H1W O2 0.85 1.89 2.665(3) 150.1 .
O5 H2W O4 0.85 1.82 2.660(3) 170.3 1_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_4
O5 Mn1 O1 C19 -43.9(2) . .
N1 Mn1 O1 C19 -154.9(2) . .
O4 Mn1 O1 C19 46.7(2) 3_755 .
N2 Mn1 O1 C19 -130.5(3) . .
O3 Mn1 O1 C19 105.4(2) 3_755 .
C21 Mn1 O1 C19 76.7(2) 3_755 .
O1 Mn1 N1 C1 -6.6(2) . .
O5 Mn1 N1 C1 -93.7(2) . .
O4 Mn1 N1 C1 115.4(3) 3_755 .
N2 Mn1 N1 C1 -179.6(3) . .
O3 Mn1 N1 C1 91.6(2) 3_755 .
C21 Mn1 N1 C1 101.1(2) 3_755 .
O1 Mn1 N1 C12 173.88(19) . .
O5 Mn1 N1 C12 86.9(2) . .
O4 Mn1 N1 C12 -64.1(3) 3_755 .
N2 Mn1 N1 C12 0.88(18) . .
O3 Mn1 N1 C12 -87.92(19) 3_755 .
C21 Mn1 N1 C12 -78.4(2) 3_755 .
O1 Mn1 N2 C10 153.7(3) . .
O5 Mn1 N2 C10 67.9(3) . .
N1 Mn1 N2 C10 179.2(3) . .
O4 Mn1 N2 C10 -23.5(3) 3_755 .
O3 Mn1 N2 C10 -81.4(3) 3_755 .
C21 Mn1 N2 C10 -52.7(3) 3_755 .
O1 Mn1 N2 C11 -25.8(4) . .
O5 Mn1 N2 C11 -111.62(19) . .
N1 Mn1 N2 C11 -0.35(18) . .
O4 Mn1 N2 C11 156.94(19) 3_755 .
O3 Mn1 N2 C11 99.05(19) 3_755 .
C21 Mn1 N2 C11 127.8(2) 3_755 .
C12 N1 C1 C2 0.0(5) . .
Mn1 N1 C1 C2 -179.5(2) . .
N1 C1 C2 C3 0.1(5) . .
C1 C2 C3 C4 -0.4(5) . .
C2 C3 C4 C12 0.5(5) . .
C2 C3 C4 C5 -178.7(3) . .
C3 C4 C5 C6 178.3(3) . .
C12 C4 C5 C6 -0.9(5) . .
C4 C5 C6 C7 1.9(5) . .
C5 C6 C7 C8 179.3(3) . .
C5 C6 C7 C11 -1.9(5) . .
C11 C7 C8 C9 0.7(5) . .
C6 C7 C8 C9 179.6(3) . .
C7 C8 C9 C10 -1.3(5) . .
C11 N2 C10 C9 -0.7(5) . .
Mn1 N2 C10 C9 179.8(2) . .
C8 C9 C10 N2 1.3(5) . .
C10 N2 C11 C7 0.1(4) . .
Mn1 N2 C11 C7 179.7(2) . .
C10 N2 C11 C12 -179.8(3) . .
Mn1 N2 C11 C12 -0.2(3) . .
C8 C7 C11 N2 -0.2(4) . .
C6 C7 C11 N2 -179.1(3) . .
C8 C7 C11 C12 179.8(3) . .
C6 C7 C11 C12 0.9(4) . .
C1 N1 C12 C4 0.2(4) . .
Mn1 N1 C12 C4 179.7(2) . .
C1 N1 C12 C11 179.1(2) . .
Mn1 N1 C12 C11 -1.3(3) . .
C3 C4 C12 N1 -0.4(4) . .
C5 C4 C12 N1 178.8(3) . .
C3 C4 C12 C11 -179.4(3) . .
C5 C4 C12 C11 -0.1(4) . .
N2 C11 C12 N1 1.0(4) . .
C7 C11 C12 N1 -178.9(2) . .
N2 C11 C12 C4 -180.0(2) . .
C7 C11 C12 C4 0.1(4) . .
C18 C13 C14 C15 2.2(4) . .
C19 C13 C14 C15 -176.8(3) . .
C18 C13 C14 C20 -173.5(2) . .
C19 C13 C14 C20 7.5(4) . .
C13 C14 C15 C16 -1.7(4) . .
C20 C14 C15 C16 174.4(3) . .
C14 C15 C16 C17 -0.4(5) . .
C15 C16 C17 C18 2.1(5) . .
C16 C17 C18 C13 -1.5(5) . .
C14 C13 C18 C17 -0.7(4) . .
C19 C13 C18 C17 178.5(3) . .
Mn1 O1 C19 O2 42.6(4) . .
Mn1 O1 C19 C13 -139.06(19) . .
C14 C13 C19 O2 -166.2(3) . .
C18 C13 C19 O2 14.7(4) . .
C14 C13 C19 O1 15.4(4) . .
C18 C13 C19 O1 -163.7(2) . .
C13 C14 C20 C21 108.7(3) . .
C15 C14 C20 C21 -67.0(3) . .
Mn1 O3 C21 O4 -7.4(2) 3_755 .
Mn1 O3 C21 C20 172.5(2) 3_755 .
Mn1 O4 C21 O3 7.5(3) 3_755 .
Mn1 O4 C21 C20 -172.5(2) 3_755 .
C14 C20 C21 O3 -40.9(4) . .
C14 C20 C21 O4 139.0(3) . .
C14 C20 C21 Mn1 61.4(18) . 3_755
