#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/29/2222970.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_2222970
loop_
_publ_author_name
'Zhao, Cheng-Qiang'
'Ou-Yang, Miao'
'Huang, Xue-Ren'
'Jiang, Yi-Min'
_publ_section_title
;Bis[2-(2-pyridylmethyleneamino)benzenesulfonato-κ³N,N',O]manganese(II)
 dihydrate
;
_journal_coeditor_code           BH2236
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1055
_journal_page_last               m1056
_journal_paper_doi               10.1107/S1600536809030670
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Mn (C12 H9 N2 O3 S)2], 2H2 O'
_chemical_formula_moiety         'C24 H18 Mn N4 O6 S2, 2(H2 O)'
_chemical_formula_sum            'C24 H22 Mn N4 O8 S2'
_chemical_formula_weight         613.52
_chemical_name_systematic
;
Bis[2-(2-pyridylmethyleneamino)benzenesulfonato-\
κ³N,N',O]manganese(II) dihydrate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.041(10)
_cell_length_b                   7.918(4)
_cell_length_c                   16.409(8)
_cell_measurement_reflns_used    4677
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      2.48
_cell_volume                     2604(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SMART APEX 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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13313
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.413
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0315
_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)+(0.0512P)²+1.5899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                1950
_reflns_number_total             2320
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2236.cif
_cod_data_source_block           I
_cod_database_code               2222970
_cod_database_fobs_code          2222970
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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_disorder_assembly
_atom_site_disorder_group
Mn Mn1 1.0000 0.18060(6) 0.2500 0.02835(15) Uani d S 1 . .
S S1 0.87380(3) 0.32706(7) 0.33859(3) 0.03333(17) Uani d . 1 . .
O O1 0.94725(8) 0.3323(2) 0.33645(9) 0.0381(4) Uani d . 1 . .
O O2 0.84921(9) 0.1575(2) 0.32866(10) 0.0508(5) Uani d . 1 . .
O O3 0.84826(8) 0.4155(2) 0.40879(9) 0.0466(4) Uani d . 1 . .
N N1 0.99221(9) -0.0275(2) 0.15711(11) 0.0352(4) Uani d . 1 . .
N N2 0.90694(8) 0.2347(2) 0.16781(10) 0.0303(4) Uani d . 1 . .
C C1 1.03597(13) -0.1521(3) 0.14852(14) 0.0444(6) Uani d . 1 . .
H H1 1.0708 -0.1601 0.1858 0.053 Uiso calc R 1 . .
C C2 1.03222(15) -0.2704(3) 0.08686(15) 0.0495(6) Uani d . 1 . .
H H2 1.0641 -0.3553 0.0826 0.059 Uiso calc R 1 . .
C C3 0.98074(14) -0.2607(3) 0.03207(16) 0.0503(6) Uani d . 1 . .
H H3 0.9767 -0.3399 -0.0095 0.060 Uiso calc R 1 . .
C C4 0.93496(13) -0.1310(3) 0.03971(14) 0.0440(6) Uani d . 1 . .
H H4 0.8998 -0.1210 0.0031 0.053 Uiso calc R 1 . .
C C5 0.94222(11) -0.0165(3) 0.10256(12) 0.0329(5) Uani d . 1 . .
C C6 0.89698(11) 0.1272(3) 0.11156(13) 0.0360(5) Uani d . 1 . .
H H6 0.8610 0.1400 0.0762 0.043 Uiso calc R 1 . .
C C7 0.86610(10) 0.3806(3) 0.17345(12) 0.0321(5) Uani d . 1 . .
C C8 0.84533(12) 0.4702(3) 0.10524(14) 0.0440(6) Uani d . 1 . .
H H8 0.8560 0.4311 0.0534 0.053 Uiso calc R 1 . .
C C9 0.80902(13) 0.6167(4) 0.11399(15) 0.0536(7) Uani d . 1 . .
H H9 0.7950 0.6754 0.0680 0.064 Uiso calc R 1 . .
C C10 0.79326(14) 0.6770(4) 0.19056(17) 0.0542(7) Uani d . 1 . .
H H10 0.7695 0.7772 0.1960 0.065 Uiso calc R 1 . .
C C11 0.81279(12) 0.5887(3) 0.25907(14) 0.0432(6) Uani d . 1 . .
H H11 0.8014 0.6283 0.3106 0.052 Uiso calc R 1 . .
C C12 0.84920(10) 0.4420(3) 0.25118(11) 0.0319(5) Uani d . 1 . .
O O4 0.79877(12) -0.0889(4) 0.44087(15) 0.1140(12) Uani d . 1 . .
H H1W 0.7570 -0.0869 0.4320 0.171 Uiso d R 1 . .
H H2W 0.8166 -0.0498 0.3988 0.171 Uiso d 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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
O1 Mn1 O1 . 3_755 111.67(10) ?
O1 Mn1 N1 . . 145.73(6) ?
O1 Mn1 N1 3_755 . 89.79(7) ?
O1 Mn1 N1 . 3_755 89.79(7) ?
O1 Mn1 N1 3_755 3_755 145.73(6) ?
N1 Mn1 N1 . 3_755 85.83(10) ?
O1 Mn1 N2 . 3_755 84.77(6) ?
O1 Mn1 N2 3_755 3_755 83.42(7) ?
N1 Mn1 N2 . 3_755 125.42(7) ?
N1 Mn1 N2 3_755 3_755 71.86(7) ?
O1 Mn1 N2 . . 83.42(6) ?
O1 Mn1 N2 3_755 . 84.77(6) ?
N1 Mn1 N2 . . 71.86(7) ?
N1 Mn1 N2 3_755 . 125.42(7) ?
N2 Mn1 N2 3_755 . 158.90(9) ?
O2 S1 O3 . . 114.95(11) ?
O2 S1 O1 . . 111.44(11) ?
O3 S1 O1 . . 111.11(9) ?
O2 S1 C12 . . 107.02(10) ?
O3 S1 C12 . . 107.40(11) ?
O1 S1 C12 . . 104.18(9) ?
S1 O1 Mn1 . . 119.62(9) ?
C1 N1 C5 . . 117.98(19) ?
C1 N1 Mn1 . . 124.77(15) ?
C5 N1 Mn1 . . 117.04(14) ?
C6 N2 C7 . . 120.13(18) ?
C6 N2 Mn1 . . 114.88(15) ?
C7 N2 Mn1 . . 124.83(13) ?
N1 C1 C2 . . 123.1(2) ?
N1 C1 H1 . . 118.5 ?
C2 C1 H1 . . 118.5 ?
C3 C2 C1 . . 118.9(2) ?
C3 C2 H2 . . 120.6 ?
C1 C2 H2 . . 120.6 ?
C2 C3 C4 . . 118.8(2) ?
C2 C3 H3 . . 120.6 ?
C4 C3 H3 . . 120.6 ?
C5 C4 C3 . . 119.0(2) ?
C5 C4 H4 . . 120.5 ?
C3 C4 H4 . . 120.5 ?
N1 C5 C4 . . 122.2(2) ?
N1 C5 C6 . . 116.40(18) ?
C4 C5 C6 . . 121.4(2) ?
N2 C6 C5 . . 119.80(19) ?
N2 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C8 C7 C12 . . 118.8(2) ?
C8 C7 N2 . . 122.43(19) ?
C12 C7 N2 . . 118.65(18) ?
C9 C8 C7 . . 120.3(2) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C8 C9 C10 . . 120.5(2) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
C11 C10 C9 . . 120.1(2) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C12 C11 C10 . . 120.0(2) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C11 C12 C7 . . 120.3(2) ?
C11 C12 S1 . . 120.34(16) ?
C7 C12 S1 . . 119.38(17) ?
H1W O4 H2W . . 105.8 ?
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 . 2.1382(16) ?
Mn1 O1 3_755 2.1382(16) ?
Mn1 N1 . 2.250(2) ?
Mn1 N1 3_755 2.250(2) ?
Mn1 N2 3_755 2.3412(19) ?
Mn1 N2 . 2.3412(19) ?
S1 O2 . 1.4395(19) ?
S1 O3 . 1.4420(17) ?
S1 O1 . 1.4729(18) ?
S1 C12 . 1.769(2) ?
N1 C1 . 1.327(3) ?
N1 C5 . 1.346(3) ?
N2 C6 . 1.271(3) ?
N2 C7 . 1.418(3) ?
C1 C2 . 1.381(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.371(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.383(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.463(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.389(3) ?
C7 C12 . 1.406(3) ?
C8 C9 . 1.376(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.381(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.380(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.378(3) ?
C11 H11 . 0.9300 ?
O4 H1W . 0.8495 ?
O4 H2W . 0.8364 ?
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
O4 H1W O3 8_755 0.85 2.14 2.993(3) 179.3 yes
O4 H2W O2 . 0.84 2.11 2.866(3) 150.6 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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S1 O1 Mn1 . . . . 41.05(13) ?
O3 S1 O1 Mn1 . . . . 170.64(10) ?
C12 S1 O1 Mn1 . . . . -74.01(13) ?
O1 Mn1 O1 S1 3_755 . . . 115.14(11) ?
N1 Mn1 O1 S1 . . . . -10.02(18) ?
N1 Mn1 O1 S1 3_755 . . . -92.28(11) ?
N2 Mn1 O1 S1 3_755 . . . -164.08(11) ?
N2 Mn1 O1 S1 . . . . 33.44(10) ?
O1 Mn1 N1 C1 . . . . -137.89(18) ?
O1 Mn1 N1 C1 3_755 . . . 91.6(2) ?
N1 Mn1 N1 C1 3_755 . . . -54.42(17) ?
N2 Mn1 N1 C1 3_755 . . . 9.8(2) ?
N2 Mn1 N1 C1 . . . . 176.1(2) ?
O1 Mn1 N1 C5 . . . . 47.5(2) ?
O1 Mn1 N1 C5 3_755 . . . -83.05(16) ?
N1 Mn1 N1 C5 3_755 . . . 130.97(18) ?
N2 Mn1 N1 C5 3_755 . . . -164.81(14) ?
N2 Mn1 N1 C5 . . . . 1.52(15) ?
O1 Mn1 N2 C6 . . . . -156.78(16) ?
O1 Mn1 N2 C6 3_755 . . . 90.65(16) ?
N1 Mn1 N2 C6 . . . . -0.84(15) ?
N1 Mn1 N2 C6 3_755 . . . -71.75(17) ?
N2 Mn1 N2 C6 3_755 . . . 146.83(16) ?
O1 Mn1 N2 C7 . . . . 27.95(16) ?
O1 Mn1 N2 C7 3_755 . . . -84.62(16) ?
N1 Mn1 N2 C7 . . . . -176.11(17) ?
N1 Mn1 N2 C7 3_755 . . . 112.98(16) ?
N2 Mn1 N2 C7 3_755 . . . -28.44(15) ?
C5 N1 C1 C2 . . . . -0.4(4) ?
Mn1 N1 C1 C2 . . . . -174.95(19) ?
N1 C1 C2 C3 . . . . -0.6(4) ?
C1 C2 C3 C4 . . . . 1.0(4) ?
C2 C3 C4 C5 . . . . -0.5(4) ?
C1 N1 C5 C4 . . . . 0.9(3) ?
Mn1 N1 C5 C4 . . . . 175.90(17) ?
C1 N1 C5 C6 . . . . -177.0(2) ?
Mn1 N1 C5 C6 . . . . -2.0(2) ?
C3 C4 C5 N1 . . . . -0.5(4) ?
C3 C4 C5 C6 . . . . 177.4(2) ?
C7 N2 C6 C5 . . . . 175.63(19) ?
Mn1 N2 C6 C5 . . . . 0.1(3) ?
N1 C5 C6 N2 . . . . 1.3(3) ?
C4 C5 C6 N2 . . . . -176.7(2) ?
C6 N2 C7 C8 . . . . -40.0(3) ?
Mn1 N2 C7 C8 . . . . 135.02(19) ?
C6 N2 C7 C12 . . . . 143.7(2) ?
Mn1 N2 C7 C12 . . . . -41.3(3) ?
C12 C7 C8 C9 . . . . 0.2(4) ?
N2 C7 C8 C9 . . . . -176.1(2) ?
C7 C8 C9 C10 . . . . 0.5(4) ?
C8 C9 C10 C11 . . . . -1.3(4) ?
C9 C10 C11 C12 . . . . 1.3(4) ?
C10 C11 C12 C7 . . . . -0.6(4) ?
C10 C11 C12 S1 . . . . -179.4(2) ?
C8 C7 C12 C11 . . . . -0.1(3) ?
N2 C7 C12 C11 . . . . 176.3(2) ?
C8 C7 C12 S1 . . . . 178.73(17) ?
N2 C7 C12 S1 . . . . -4.8(3) ?
O2 S1 C12 C11 . . . . 124.5(2) ?
O3 S1 C12 C11 . . . . 0.6(2) ?
O1 S1 C12 C11 . . . . -117.32(19) ?
O2 S1 C12 C7 . . . . -54.3(2) ?
O3 S1 C12 C7 . . . . -178.25(17) ?
O1 S1 C12 C7 . . . . 63.82(19) ?
