#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:43:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180516 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/85/7218509.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_7218509
loop_
_publ_author_name
'Zitzer, Christina'
'Muesmann, Thomas W. T.'
'Christoffers, Jens'
'Schwickert, Christian'
'Pöttgen, Rainer'
'Wickleder, Mathias S.'
_publ_section_title
;
 1,2,4,5-Benzenetetrasulfonic acid and 1,4-benzenedisulfonic acid as sulfo
 analogues of pyromellitic and terephthalic acids for building
 coordination polymers of manganese
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              11064
_journal_paper_doi               10.1039/C4CE01618A
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C12 H18 Mn N2 O8 S2'
_chemical_formula_sum            'C12 H18 Mn N2 O8 S2'
_chemical_formula_weight         437.34
_chemical_name_common
'(manganese(II)-benzenedisulfonoc acid)(dimethylformamide)'
_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           SHELXL-97
_cell_angle_alpha                93.552(8)
_cell_angle_beta                 99.993(7)
_cell_angle_gamma                99.237(7)
_cell_formula_units_Z            1
_cell_length_a                   5.1430(7)
_cell_length_b                   9.2620(12)
_cell_length_c                   9.4020(13)
_cell_measurement_temperature    120(2)
_cell_volume                     433.48(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9686
_diffrn_reflns_theta_full        33.78
_diffrn_reflns_theta_max         33.78
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    1.046
_exptl_absorpt_correction_T_max  0.9447
_exptl_absorpt_correction_T_min  0.8972
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SAINT'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             225
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0290
_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)+(0.0317P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0670
_reflns_number_gt                2587
_reflns_number_total             3443
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01618a1.cif
_cod_data_source_block           c:\cz316\cz316
_cod_depositor_comments
'Adding full bibliography for 7218507--7218511.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7218509
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.0000 0.5000 0.5000 0.00983(7) Uani 1 2 d S . .
S1 S 0.58756(6) 0.71419(3) 0.65128(3) 0.01166(7) Uani 1 1 d . . .
O11 O 0.32232(17) 0.63366(9) 0.65915(9) 0.01331(18) Uani 1 1 d . . .
O12 O 0.72421(19) 0.63365(10) 0.55880(11) 0.0189(2) Uani 1 1 d . . .
O13 O 0.7448(2) 0.76489(11) 0.79317(10) 0.0220(2) Uani 1 1 d . . .
C1 C 0.5339(2) 0.87272(13) 0.56292(13) 0.0108(2) Uani 1 1 d . . .
C2 C 0.6781(3) 0.91501(14) 0.45652(15) 0.0159(2) Uani 1 1 d . . .
H21 H 0.7983 0.8564 0.4270 0.019 Uiso 1 1 calc R . .
C3 C 0.3554(3) 0.95570(14) 0.60660(15) 0.0165(3) Uani 1 1 d . . .
H31 H 0.2567 0.9245 0.6791 0.020 Uiso 1 1 calc R . .
O1 O 0.06537(19) 0.64632(10) 0.33579(10) 0.01669(19) Uani 1 1 d . . .
C11 C 0.2098(8) 0.6510(4) 0.2465(5) 0.0183(7) Uani 0.50 1 d P A 1
H111 H 0.3364 0.5863 0.2520 0.022 Uiso 0.50 1 calc PR A 1
N1 N 0.2030(11) 0.7402(4) 0.1418(5) 0.0176(8) Uani 0.50 1 d P A 1
C13 C 0.3827(7) 0.7418(4) 0.0382(4) 0.0362(8) Uani 0.50 1 d P A 1
H131 H 0.4898 0.8403 0.0438 0.043 Uiso 0.50 1 calc PR A 1
H132 H 0.2775 0.7157 -0.0600 0.043 Uiso 0.50 1 calc PR A 1
H133 H 0.5021 0.6706 0.0610 0.043 Uiso 0.50 1 calc PR A 1
C12 C 0.0244(8) 0.8467(4) 0.1322(4) 0.0252(8) Uani 0.50 1 d P A 1
H121 H -0.1096 0.8217 0.1933 0.038 Uiso 0.50 1 calc PR A 1
H123 H -0.0662 0.8455 0.0314 0.038 Uiso 0.50 1 calc PR A 1
H122 H 0.1280 0.9449 0.1656 0.038 Uiso 0.50 1 calc PR A 1
C11A C 0.1348(7) 0.6079(4) 0.2175(4) 0.0149(7) Uani 0.50 1 d P A 2
H114 H 0.1596 0.5091 0.2022 0.018 Uiso 0.50 1 calc PR A 2
N1A N 0.1745(10) 0.6944(4) 0.1154(5) 0.0161(7) Uani 0.50 1 d P A 2
C13A C 0.2500(6) 0.6412(4) -0.0189(3) 0.0256(6) Uani 0.50 1 d P A 2
H134 H 0.1207 0.6601 -0.1022 0.031 Uiso 0.50 1 calc PR A 2
H135 H 0.2504 0.5353 -0.0196 0.031 Uiso 0.50 1 calc PR A 2
H136 H 0.4295 0.6924 -0.0247 0.031 Uiso 0.50 1 calc PR A 2
C12A C 0.1510(8) 0.8490(4) 0.1297(4) 0.0233(8) Uani 0.50 1 d P A 2
H124 H 0.0136 0.8686 0.0507 0.028 Uiso 0.50 1 calc PR A 2
H125 H 0.3235 0.9097 0.1252 0.028 Uiso 0.50 1 calc PR A 2
H126 H 0.1001 0.8729 0.2230 0.028 Uiso 0.50 1 calc PR A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
O12 Mn1 O12 180.0 2_666 1_455
O12 Mn1 O1 93.09(4) 2_666 .
O12 Mn1 O1 86.91(4) 1_455 .
O12 Mn1 O1 86.91(4) 2_666 2_566
O12 Mn1 O1 93.09(4) 1_455 2_566
O1 Mn1 O1 180.00(5) . 2_566
O12 Mn1 O11 90.16(4) 2_666 .
O12 Mn1 O11 89.84(4) 1_455 .
O1 Mn1 O11 91.86(4) . .
O1 Mn1 O11 88.14(4) 2_566 .
O12 Mn1 O11 89.84(4) 2_666 2_566
O12 Mn1 O11 90.16(4) 1_455 2_566
O1 Mn1 O11 88.14(3) . 2_566
O1 Mn1 O11 91.86(4) 2_566 2_566
O11 Mn1 O11 179.999(1) . 2_566
O13 S1 O12 114.01(6) . .
O13 S1 O11 112.01(6) . .
O12 S1 O11 112.07(5) . .
O13 S1 C1 106.61(6) . .
O12 S1 C1 105.02(6) . .
O11 S1 C1 106.41(6) . .
S1 O11 Mn1 133.74(5) . .
S1 O12 Mn1 158.66(7) . 1_655
C2 C1 C3 121.37(11) . .
C2 C1 S1 119.76(9) . .
C3 C1 S1 118.81(10) . .
C1 C2 C3 119.17(12) . 2_676
C1 C2 H21 120.4 . .
C3 C2 H21 120.4 2_676 .
C1 C3 C2 119.46(12) . 2_676
C1 C3 H31 120.3 . .
C2 C3 H31 120.3 2_676 .
C11 O1 Mn1 132.6(2) . .
C11A O1 Mn1 123.63(19) . .
O1 C11 N1 124.4(4) . .
O1 C11 H111 117.8 . .
N1 C11 H111 117.8 . .
C11 N1 C12 120.4(4) . .
C11 N1 C13 122.0(4) . .
C12 N1 C13 117.5(4) . .
O1 C11A N1A 124.9(4) . .
O1 C11A H114 117.5 . .
N1A C11A H114 117.5 . .
C11A N1A C12A 122.1(4) . .
C11A N1A C13A 121.7(3) . .
C12A N1A C13A 116.2(4) . .
N1A C13A H134 109.5 . .
N1A C13A H135 109.5 . .
H134 C13A H135 109.5 . .
N1A C13A H136 109.5 . .
H134 C13A H136 109.5 . .
H135 C13A H136 109.5 . .
N1A C12A H124 109.5 . .
N1A C12A H125 109.5 . .
H124 C12A H125 109.5 . .
N1A C12A H126 109.5 . .
H124 C12A H126 109.5 . .
H125 C12A H126 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O12 2.1449(9) 2_666
Mn1 O12 2.1449(9) 1_455
Mn1 O1 2.1509(9) .
Mn1 O1 2.1509(9) 2_566
Mn1 O11 2.1841(9) .
Mn1 O11 2.1841(9) 2_566
S1 O13 1.4424(10) .
S1 O12 1.4514(10) .
S1 O11 1.4621(9) .
S1 C1 1.7675(12) .
O12 Mn1 2.1450(9) 1_655
C1 C2 1.3843(18) .
C1 C3 1.3858(18) .
C2 C3 1.3909(18) 2_676
C2 H21 0.9500 .
C3 C2 1.3908(18) 2_676
C3 H31 0.9500 .
O1 C11 1.212(5) .
O1 C11A 1.272(4) .
C11 N1 1.324(7) .
C11 H111 0.9500 .
N1 C12 1.448(6) .
N1 C13 1.453(6) .
C13 H131 0.9800 .
C13 H132 0.9800 .
C13 H133 0.9800 .
C12 H121 0.9800 .
C12 H123 0.9800 .
C12 H122 0.9800 .
C11A N1A 1.310(7) .
C11A H114 0.9500 .
N1A C12A 1.457(5) .
N1A C13A 1.464(5) .
C13A H134 0.9800 .
C13A H135 0.9800 .
C13A H136 0.9800 .
C12A H124 0.9800 .
C12A H125 0.9800 .
C12A H126 0.9800 .
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
O13 S1 O11 Mn1 -169.80(7) . .
O12 S1 O11 Mn1 -40.20(9) . .
C1 S1 O11 Mn1 74.07(8) . .
O12 Mn1 O11 S1 54.09(8) 2_666 .
O12 Mn1 O11 S1 -125.91(8) 1_455 .
O1 Mn1 O11 S1 -39.00(8) . .
O1 Mn1 O11 S1 141.00(8) 2_566 .
O13 S1 O12 Mn1 26.28(19) . 1_655
O11 S1 O12 Mn1 -102.28(17) . 1_655
C1 S1 O12 Mn1 142.61(16) . 1_655
O13 S1 C1 C2 104.26(11) . .
O12 S1 C1 C2 -17.05(12) . .
O11 S1 C1 C2 -136.04(10) . .
O13 S1 C1 C3 -73.01(11) . .
O12 S1 C1 C3 165.68(10) . .
O11 S1 C1 C3 46.69(11) . .
C3 C1 C2 C3 0.7(2) . 2_676
S1 C1 C2 C3 -176.54(10) . 2_676
C2 C1 C3 C2 -0.7(2) . 2_676
S1 C1 C3 C2 176.56(10) . 2_676
O12 Mn1 O1 C11 -1.3(2) 2_666 .
O12 Mn1 O1 C11 178.7(2) 1_455 .
O11 Mn1 O1 C11 88.9(2) . .
O11 Mn1 O1 C11 -91.1(2) 2_566 .
O12 Mn1 O1 C11A 27.9(2) 2_666 .
O12 Mn1 O1 C11A -152.1(2) 1_455 .
O11 Mn1 O1 C11A 118.2(2) . .
O11 Mn1 O1 C11A -61.8(2) 2_566 .
C11A O1 C11 N1 93.6(9) . .
Mn1 O1 C11 N1 172.0(2) . .
O1 C11 N1 C12 3.3(6) . .
O1 C11 N1 C13 179.5(3) . .
C11 O1 C11A N1A -60.5(8) . .
Mn1 O1 C11A N1A 179.6(3) . .
O1 C11A N1A C12A 2.1(7) . .
O1 C11A N1A C13A -179.0(3) . .
