#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/92/2209267.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_2209267
loop_
_publ_author_name
'Zhi-Yong Wu'
'Jie Zhang'
'Yong Huang'
'Yan-Tuan Li'
'Wei Sun'
_publ_section_title
;
 cis-Dichlorobis(2,2'-diamino-4,4'-bi-1,3-thiazole)manganese(II)
 methanol solvate
;
_journal_coeditor_code           NG2036
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1232
_journal_page_last               m1234
_journal_paper_doi               10.1107/S160053680601539X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Mn Cl2 (C6 H6 N4 S2)2], C H4 O'
_chemical_formula_moiety         'C12 H12 Cl2 Mn N8 S4, C H4 O'
_chemical_formula_sum            'C13 H16 Cl2 Mn N8 O S4'
_chemical_formula_weight         554.42
_chemical_name_systematic
;
cis-Dichlorobis(2,2'-diamino-4,4'-bi-1,3-thiazole)manganese(II) methanol
solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 108.39(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.451(2)
_cell_length_b                   13.614(3)
_cell_length_c                   14.892(3)
_cell_measurement_reflns_used    4763
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.768
_cell_measurement_theta_min      2.398
_cell_volume                     2203.0(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16004
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  0.9070
_exptl_absorpt_correction_T_min  0.7380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.503
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0568
_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)+(0.0542P)²+3.4155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                3543
_reflns_number_total             3992
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2036.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209267
_cod_database_fobs_code          2209267
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Mn Mn1 0.21349(5) 0.15786(4) 0.29063(4) 0.03584(19) Uani d . 1
Cl Cl1 0.06956(10) 0.19672(8) 0.38513(8) 0.0489(3) Uani d . 1
Cl Cl2 0.38139(10) 0.26968(8) 0.38847(8) 0.0478(3) Uani d . 1
N N1 0.3358(3) 0.0958(3) 0.2115(3) 0.0458(9) Uani d . 1
N N2 0.3005(3) 0.0227(2) 0.3706(3) 0.0437(9) Uani d . 1
N N3 0.3183(4) 0.2065(4) 0.0872(3) 0.0698(13) Uani d . 1
H H3A 0.2779 0.2485 0.1090 0.084 Uiso calc R 1
H H3B 0.3347 0.2187 0.0359 0.084 Uiso calc R 1
N N4 0.2464(4) 0.0247(3) 0.5094(3) 0.0622(11) Uani d . 1
H H4A 0.2000 0.0753 0.4912 0.075 Uiso calc R 1
H H4B 0.2539 -0.0017 0.5634 0.075 Uiso calc R 1
N N5 0.0548(3) 0.0761(2) 0.1757(2) 0.0404(8) Uani d . 1
N N6 0.1158(3) 0.2732(2) 0.1851(2) 0.0403(8) Uani d . 1
N N7 0.0826(4) -0.0939(3) 0.1972(3) 0.0617(11) Uani d . 1
H H7A 0.1515 -0.0868 0.2416 0.074 Uiso calc R 1
H H7B 0.0542 -0.1517 0.1801 0.074 Uiso calc R 1
N N8 0.2297(4) 0.4181(3) 0.2337(3) 0.0651(12) Uani d . 1
H H8A 0.2911 0.3872 0.2716 0.078 Uiso calc R 1
H H8B 0.2323 0.4809 0.2285 0.078 Uiso calc R 1
S S1 0.43960(14) 0.03567(15) 0.09235(12) 0.0857(6) Uani d . 1
S S2 0.40131(12) -0.11306(10) 0.49067(12) 0.0708(5) Uani d . 1
S S3 -0.11698(13) -0.02778(11) 0.06307(11) 0.0709(4) Uani d . 1
S S4 0.00675(12) 0.42925(9) 0.10428(10) 0.0589(4) Uani d . 1
C C1 0.3559(4) 0.1210(4) 0.1340(4) 0.0547(12) Uani d . 1
C C2 0.4469(5) -0.0373(5) 0.1888(5) 0.0768(17) Uani d . 1
H H2 0.4861 -0.0980 0.2007 0.092 Uiso calc R 1
C C3 0.3888(4) 0.0047(4) 0.2442(4) 0.0547(13) Uani d . 1
C C4 0.3053(4) -0.0120(3) 0.4552(4) 0.0485(11) Uani d . 1
C C5 0.4368(4) -0.1079(4) 0.3902(5) 0.0714(18) Uani d . 1
H H5 0.4894 -0.1517 0.3743 0.086 Uiso calc R 1
C C6 0.3782(4) -0.0300(3) 0.3333(4) 0.0525(12) Uani d . 1
C C7 0.0197(4) -0.0149(3) 0.1550(3) 0.0472(11) Uani d . 1
C C8 -0.1251(5) 0.0975(4) 0.0513(4) 0.0683(15) Uani d . 1
H H8 -0.1882 0.1312 0.0071 0.082 Uiso calc R 1
C C9 -0.0272(4) 0.1405(3) 0.1150(3) 0.0466(11) Uani d . 1
C C10 0.1302(4) 0.3685(3) 0.1830(3) 0.0453(10) Uani d . 1
C C11 -0.0671(4) 0.3184(4) 0.0748(4) 0.0551(12) Uani d . 1
H H11 -0.1448 0.3105 0.0308 0.066 Uiso calc R 1
C C12 0.0018(4) 0.2448(3) 0.1234(3) 0.0454(10) Uani d . 1
C C13 0.2887(8) 0.6906(6) 0.2152(7) 0.130(4) Uani d . 1
H H13A 0.2738 0.7517 0.1813 0.194 Uiso calc R 1
H H13B 0.3718 0.6698 0.2243 0.194 Uiso calc R 1
H H13C 0.2766 0.6991 0.2756 0.194 Uiso calc R 1
O O1 0.2069(4) 0.6192(3) 0.1631(3) 0.0806(12) Uani d . 1
H H1 0.1360 0.6377 0.1539 0.121 Uiso calc 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'
Cl Cl 0.1484 0.1585 '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'
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_publ_flag
N1 Mn1 N2 74.07(14) y
N1 Mn1 N5 84.68(13) y
N1 Mn1 N6 98.62(14) y
N1 Mn1 Cl1 170.06(11) y
N1 Mn1 Cl2 92.41(10) y
N2 Mn1 N5 96.31(12) y
N2 Mn1 N6 168.48(13) y
N2 Mn1 Cl1 97.71(10) y
N2 Mn1 Cl2 93.34(10) y
N5 Mn1 N6 73.87(13) y
N5 Mn1 Cl1 90.81(9) y
N5 Mn1 Cl2 168.73(9) y
N6 Mn1 Cl1 88.59(10) y
N6 Mn1 Cl2 95.88(10) y
Cl1 Mn1 Cl2 93.66(5) y
C1 N1 C3 111.4(4) ?
C1 N1 Mn1 132.9(3) ?
C3 N1 Mn1 115.0(3) ?
C4 N2 C6 110.8(4) ?
C4 N2 Mn1 132.2(3) ?
C6 N2 Mn1 116.4(3) ?
C1 N3 H3A 120.0 ?
C1 N3 H3B 120.0 ?
H3A N3 H3B 120.0 ?
C4 N4 H4A 120.0 ?
C4 N4 H4B 120.0 ?
H4A N4 H4B 120.0 ?
C7 N5 C9 110.4(4) ?
C7 N5 Mn1 136.9(3) ?
C9 N5 Mn1 112.6(3) ?
C10 N6 C12 110.9(4) ?
C10 N6 Mn1 132.0(3) ?
C12 N6 Mn1 115.0(3) ?
C7 N7 H7A 120.0 ?
C7 N7 H7B 120.0 ?
H7A N7 H7B 120.0 ?
C10 N8 H8A 120.0 ?
C10 N8 H8B 120.0 ?
H8A N8 H8B 120.0 ?
C2 S1 C1 88.6(3) ?
C5 S2 C4 90.2(2) ?
C8 S3 C7 89.3(2) ?
C11 S4 C10 89.1(2) ?
N1 C1 N3 124.7(4) ?
N1 C1 S1 114.5(4) ?
N3 C1 S1 120.8(4) ?
C3 C2 S1 111.3(5) ?
C3 C2 H2 124.4 ?
S1 C2 H2 124.4 ?
C2 C3 N1 114.2(5) ?
C2 C3 C6 128.7(5) ?
N1 C3 C6 117.1(4) ?
N4 C4 N2 125.1(4) ?
N4 C4 S2 121.2(4) ?
N2 C4 S2 113.7(4) ?
C6 C5 S2 111.7(4) ?
C6 C5 H5 124.1 ?
S2 C5 H5 124.1 ?
N2 C6 C5 113.4(5) ?
N2 C6 C3 116.6(4) ?
C5 C6 C3 130.0(5) ?
N5 C7 N7 124.8(4) ?
N5 C7 S3 114.6(4) ?
N7 C7 S3 120.6(3) ?
C9 C8 S3 110.6(4) ?
C9 C8 H8 124.7 ?
S3 C8 H8 124.7 ?
C8 C9 N5 115.0(4) ?
C8 C9 C12 126.8(4) ?
N5 C9 C12 118.1(4) ?
N6 C10 N8 125.3(4) ?
N6 C10 S4 114.0(3) ?
N8 C10 S4 120.6(3) ?
C12 C11 S4 111.1(4) ?
C12 C11 H11 124.4 ?
S4 C11 H11 124.4 ?
C11 C12 N6 114.8(4) ?
C11 C12 C9 127.2(4) ?
N6 C12 C9 117.9(4) ?
O1 C13 H13A 109.5 ?
O1 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
O1 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C13 O1 H1 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 Cl1 2.5378(14) y
Mn1 Cl2 2.5239(14) y
Mn1 N1 2.259(4) y
Mn1 N2 2.247(3) y
Mn1 N5 2.347(3) y
Mn1 N6 2.253(3) y
N1 C1 1.293(6) ?
N1 C3 1.398(6) ?
N2 C4 1.331(6) ?
N2 C6 1.387(6) ?
N3 C1 1.355(7) ?
N3 H3A 0.8600 ?
N3 H3B 0.8600 ?
N4 C4 1.304(6) ?
N4 H4A 0.8600 ?
N4 H4B 0.8600 ?
N5 C7 1.309(5) ?
N5 C9 1.391(6) ?
N6 C10 1.310(6) ?
N6 C12 1.393(5) ?
N7 C7 1.336(6) ?
N7 H7A 0.8600 ?
N7 H7B 0.8600 ?
N8 C10 1.334(6) ?
N8 H8A 0.8600 ?
N8 H8B 0.8600 ?
S1 C2 1.726(7) ?
S1 C1 1.740(5) ?
S2 C5 1.671(7) ?
S2 C4 1.736(5) ?
S3 C8 1.714(6) ?
S3 C7 1.733(5) ?
S4 C11 1.719(5) ?
S4 C10 1.735(4) ?
C2 C3 1.341(7) ?
C2 H2 0.9300 ?
C3 C6 1.450(8) ?
C5 C6 1.391(7) ?
C5 H5 0.9300 ?
C8 C9 1.353(7) ?
C8 H8 0.9300 ?
C9 C12 1.455(6) ?
C11 C12 1.338(6) ?
C11 H11 0.9300 ?
C13 O1 1.402(8) ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
O1 H1 0.8200 ?
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
O1 H1 Cl1 2 0.82 2.38 3.197(4) 175.3
N3 H3A N6 . 0.86 2.48 3.233(6) 146.0
N3 H3B Cl2 4_565 0.86 2.42 3.277(4) 172.6
N4 H4A Cl1 . 0.86 2.44 3.263(4) 159.5
N4 H4B O1 4_566 0.86 2.36 3.152(6) 153.8
N7 H7A N2 . 0.86 2.60 3.369(5) 149.5
N7 H7B Cl1 2_545 0.86 2.52 3.364(4) 168.4
N8 H8A Cl2 . 0.86 2.35 3.144(4) 153.7
N8 H8B O1 . 0.86 2.10 2.915(6) 158.6
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
N2 Mn1 N1 C1 176.5(4)
N6 Mn1 N1 C1 5.6(4)
N5 Mn1 N1 C1 78.4(4)
Cl2 Mn1 N1 C1 -90.7(4)
N2 Mn1 N1 C3 6.6(3)
N6 Mn1 N1 C3 -164.3(3)
N5 Mn1 N1 C3 -91.5(3)
Cl2 Mn1 N1 C3 99.4(3)
N6 Mn1 N2 C4 -139.9(6)
N1 Mn1 N2 C4 168.5(4)
N5 Mn1 N2 C4 -108.9(4)
Cl2 Mn1 N2 C4 76.9(4)
Cl1 Mn1 N2 C4 -17.3(4)
N6 Mn1 N2 C6 50.0(8)
N1 Mn1 N2 C6 -1.6(3)
N5 Mn1 N2 C6 81.0(3)
Cl2 Mn1 N2 C6 -93.2(3)
Cl1 Mn1 N2 C6 172.7(3)
N2 Mn1 N5 C7 -1.7(5)
N6 Mn1 N5 C7 172.2(5)
N1 Mn1 N5 C7 71.6(4)
Cl2 Mn1 N5 C7 147.0(4)
Cl1 Mn1 N5 C7 -99.6(4)
N2 Mn1 N5 C9 175.3(3)
N6 Mn1 N5 C9 -10.8(3)
N1 Mn1 N5 C9 -111.4(3)
Cl2 Mn1 N5 C9 -36.0(6)
Cl1 Mn1 N5 C9 77.5(3)
N2 Mn1 N6 C10 -151.9(6)
N1 Mn1 N6 C10 -102.2(4)
N5 Mn1 N6 C10 176.0(4)
Cl2 Mn1 N6 C10 -8.8(4)
Cl1 Mn1 N6 C10 84.7(4)
N2 Mn1 N6 C12 46.4(8)
N1 Mn1 N6 C12 96.1(3)
N5 Mn1 N6 C12 14.3(3)
Cl2 Mn1 N6 C12 -170.5(3)
Cl1 Mn1 N6 C12 -77.0(3)
C3 N1 C1 N3 -178.3(4)
Mn1 N1 C1 N3 11.6(7)
C3 N1 C1 S1 0.8(5)
Mn1 N1 C1 S1 -169.4(2)
C2 S1 C1 N1 -0.4(4)
C2 S1 C1 N3 178.7(4)
C1 S1 C2 C3 -0.1(4)
S1 C2 C3 N1 0.5(6)
S1 C2 C3 C6 -177.1(4)
C1 N1 C3 C2 -0.8(6)
Mn1 N1 C3 C2 171.2(4)
C1 N1 C3 C6 177.1(4)
Mn1 N1 C3 C6 -10.9(5)
C6 N2 C4 N4 177.1(4)
Mn1 N2 C4 N4 6.7(7)
C6 N2 C4 S2 -2.0(5)
Mn1 N2 C4 S2 -172.4(2)
C5 S2 C4 N4 -178.6(4)
C5 S2 C4 N2 0.5(4)
C4 S2 C5 C6 1.1(4)
C4 N2 C6 C5 2.8(5)
Mn1 N2 C6 C5 174.9(3)
C4 N2 C6 C3 -175.6(4)
Mn1 N2 C6 C3 -3.5(5)
S2 C5 C6 N2 -2.4(5)
S2 C5 C6 C3 175.7(4)
C2 C3 C6 N2 -172.8(5)
N1 C3 C6 N2 9.6(6)
C2 C3 C6 C5 9.1(9)
N1 C3 C6 C5 -168.5(5)
C9 N5 C7 N7 176.3(4)
Mn1 N5 C7 N7 -6.6(8)
C9 N5 C7 S3 -1.8(5)
Mn1 N5 C7 S3 175.3(2)
C8 S3 C7 N5 1.0(4)
C8 S3 C7 N7 -177.3(4)
C7 S3 C8 C9 0.2(5)
S3 C8 C9 N5 -1.3(6)
S3 C8 C9 C12 176.3(4)
C7 N5 C9 C8 2.0(6)
Mn1 N5 C9 C8 -175.8(4)
C7 N5 C9 C12 -175.8(4)
Mn1 N5 C9 C12 6.4(5)
C12 N6 C10 N8 -179.7(5)
Mn1 N6 C10 N8 18.0(7)
C12 N6 C10 S4 -1.0(5)
Mn1 N6 C10 S4 -163.3(2)
C11 S4 C10 N6 0.6(4)
C11 S4 C10 N8 179.4(4)
C10 S4 C11 C12 0.0(4)
S4 C11 C12 N6 -0.5(6)
S4 C11 C12 C9 -177.3(4)
C10 N6 C12 C11 1.0(6)
Mn1 N6 C12 C11 166.5(3)
C10 N6 C12 C9 178.1(4)
Mn1 N6 C12 C9 -16.3(5)
C8 C9 C12 C11 5.6(9)
N5 C9 C12 C11 -176.9(5)
C8 C9 C12 N6 -171.2(5)
N5 C9 C12 N6 6.3(6)
