##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-06-06
_journal_date_accepted     2010-06-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     m777
_journal_page_last     m777
_journal_paper_category     QM
_journal_coeditor_code     HB5486
_publ_contact_author_name     'Fu-Ming Wang'
_publ_contact_author_address
;
Department of Chemistry
Dezhou University
Dezhou Shandong 253023
People's Republic of China
;
_publ_contact_author_email     wfm99999@126.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
{N,N'-Bis[1-(2-pyridyl)ethylidene]propane-1,2-diamine-\
κ⁴N,N',N'',N'''}bis(thiocyanato-κN)\
manganese(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Fu-Ming Wang'
;
Department of Chemistry
Dezhou University
Dezhou Shandong 253023
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
{N,N'-Bis[1-(2-pyridyl)ethylidene]propane-1,2-diamine-
κ⁴N,N',N'',N'''}bis(thiocyanato-
κN)manganese(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H20 Mn N6 S2'
_chemical_formula_sum     'C19 H20 Mn N6 S2'
_chemical_formula_iupac     '[Mn (N C S)2 (C17 H20 N4)]'
_chemical_formula_weight     451.47
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.647(3)
_cell_length_b     9.135(2)
_cell_length_c     14.608(3)
_cell_angle_alpha     84.701(3)
_cell_angle_beta     79.407(3)
_cell_angle_gamma     70.509(3)
_cell_volume     1068.6(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1307
_cell_measurement_theta_min     2.3
_cell_measurement_theta_max     24.5
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     brown
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.403
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     466
_exptl_absorpt_coefficient_mu     0.830
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.771
_exptl_absorpt_correction_T_max     0.789
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11100
_diffrn_reflns_av_R_equivalents     0.0781
_diffrn_reflns_av_sigmaI/netI     0.1108
_diffrn_reflns_theta_min     2.37
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     4608
_reflns_number_gt     2211
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1624
_refine_ls_R_factor_gt     0.0772
_refine_ls_wR_factor_gt     0.1797
_refine_ls_wR_factor_ref     0.2235
_refine_ls_goodness_of_fit_ref     0.986
_refine_ls_restrained_S_all     0.986
_refine_ls_number_reflns     4608
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.1044P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.678
_refine_diff_density_min     -0.335
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Mn' 'Mn' 0.3368 0.7283
                         '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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 1.02210(10) 0.54382(9) 0.27241(5) 0.0601(3) Uani d . 1 . .
    N N1 1.2061(6) 0.6565(5) 0.3134(3) 0.0644(12) Uani d . 1 . .
    N N2 1.0220(6) 0.7580(5) 0.1819(3) 0.0673(12) Uani d . 1 . .
    N N3 0.8157(6) 0.5912(5) 0.1875(3) 0.0701(13) Uani d . 1 . .
    N N4 0.9013(5) 0.3471(5) 0.3008(3) 0.0665(12) Uani d . 1 . .
    N N5 0.8737(7) 0.6394(7) 0.3994(4) 0.0906(17) Uani d . 1 . .
    N N6 1.2282(6) 0.3744(6) 0.1940(4) 0.0772(15) Uani d . 1 . .
    S S1 0.6757(2) 0.8093(2) 0.54416(16) 0.1097(7) Uani d . 1 . .
    S S2 1.4735(2) 0.1575(2) 0.08162(12) 0.0855(5) Uani d . 1 . .
    C C1 1.2937(8) 0.6060(8) 0.3826(5) 0.089(2) Uani d . 1 . .
    H H1 1.2883 0.5148 0.4151 0.107 Uiso calc R 1 . .
    C C2 1.3917(9) 0.6811(8) 0.4088(5) 0.096(2) Uani d . 1 . .
    H H2 1.4508 0.6422 0.4578 0.116 Uiso calc R 1 . .
    C C3 1.3997(8) 0.8144(8) 0.3608(5) 0.088(2) Uani d . 1 . .
    H H3 1.4654 0.8677 0.3765 0.106 Uiso calc R 1 . .
    C C4 1.3109(7) 0.8693(6) 0.2897(5) 0.0750(17) Uani d . 1 . .
    H H4 1.3155 0.9601 0.2565 0.090 Uiso calc R 1 . .
    C C5 1.2135(6) 0.7880(6) 0.2674(4) 0.0574(13) Uani d . 1 . .
    C C6 1.1124(7) 0.8394(7) 0.1905(4) 0.0631(14) Uani d . 1 . .
    C C7 1.1270(9) 0.9785(7) 0.1307(5) 0.095(2) Uani d . 1 . .
    H H7A 1.2372 0.9548 0.0956 0.142 Uiso calc R 1 . .
    H H7B 1.1054 1.0646 0.1696 0.142 Uiso calc R 1 . .
    H H7C 1.0477 1.0050 0.0888 0.142 Uiso calc R 1 . .
    C C8 0.9234(8) 0.7889(8) 0.1062(4) 0.087(2) Uani d . 1 . .
    H H8 0.8913 0.8996 0.0880 0.104 Uiso calc R 1 . .
    C C9 1.0322(10) 0.6917(9) 0.0230(5) 0.106(2) Uani d . 1 . .
    H H9A 1.1312 0.7198 0.0042 0.159 Uiso calc R 1 . .
    H H9B 0.9712 0.7114 -0.0281 0.159 Uiso calc R 1 . .
    H H9C 1.0619 0.5833 0.0409 0.159 Uiso calc R 1 . .
    C C10 0.7743(8) 0.7434(8) 0.1372(5) 0.098(2) Uani d . 1 . .
    H H10A 0.7250 0.7379 0.0837 0.118 Uiso calc R 1 . .
    H H10B 0.6935 0.8213 0.1779 0.118 Uiso calc R 1 . .
    C C11 0.7315(7) 0.4988(6) 0.1900(4) 0.0617(14) Uani d . 1 . .
    C C12 0.5892(7) 0.5241(7) 0.1393(5) 0.0843(19) Uani d . 1 . .
    H H12A 0.5809 0.6123 0.0970 0.126 Uiso calc R 1 . .
    H H12B 0.4880 0.5428 0.1833 0.126 Uiso calc R 1 . .
    H H12C 0.6072 0.4335 0.1050 0.126 Uiso calc R 1 . .
    C C13 0.7763(6) 0.3606(6) 0.2541(4) 0.0613(14) Uani d . 1 . .
    C C14 0.6956(7) 0.2485(8) 0.2671(5) 0.0826(18) Uani d . 1 . .
    H H14 0.6105 0.2573 0.2340 0.099 Uiso calc R 1 . .
    C C15 0.7432(8) 0.1242(8) 0.3297(5) 0.094(2) Uani d . 1 . .
    H H15 0.6899 0.0495 0.3389 0.112 Uiso calc R 1 . .
    C C16 0.8672(9) 0.1124(8) 0.3771(5) 0.094(2) Uani d . 1 . .
    H H16 0.9006 0.0303 0.4195 0.112 Uiso calc R 1 . .
    C C17 0.9429(8) 0.2251(7) 0.3610(4) 0.0808(18) Uani d . 1 . .
    H H17 1.0283 0.2165 0.3937 0.097 Uiso calc R 1 . .
    C C18 0.7938(7) 0.7096(6) 0.4577(4) 0.0589(14) Uani d . 1 . .
    C C19 1.3320(7) 0.2828(7) 0.1471(4) 0.0631(15) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 N5 . 2.127(6) y
    Mn1 N6 . 2.149(6) y
    Mn1 N2 . 2.258(5) y
    Mn1 N3 . 2.260(4) y
    Mn1 N4 . 2.334(4) y
    Mn1 N1 . 2.346(4) y
    N1 C1 . 1.331(7) ?
    N1 C5 . 1.336(6) ?
    N2 C6 . 1.274(6) ?
    N2 C8 . 1.470(7) ?
    N3 C11 . 1.281(6) ?
    N3 C10 . 1.476(7) ?
    N4 C17 . 1.345(7) ?
    N4 C13 . 1.348(6) ?
    N5 C18 . 1.097(7) ?
    N6 C19 . 1.164(7) ?
    S1 C18 . 1.608(7) ?
    S2 C19 . 1.600(7) ?
    C1 C2 . 1.376(8) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.364(9) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.364(8) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.389(7) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.495(7) ?
    C6 C7 . 1.501(8) ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 C10 . 1.465(8) ?
    C8 C9 . 1.540(9) ?
    C8 H8 . 0.9800 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C13 . 1.486(8) ?
    C11 C12 . 1.493(7) ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 C14 . 1.402(7) ?
    C14 C15 . 1.389(8) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.351(8) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.376(8) ?
    C16 H16 . 0.9300 ?
    C17 H17 . 0.9300 ?
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
    N5 Mn1 N6 . . 152.6(2) n
    N5 Mn1 N2 . . 102.5(2) n
    N6 Mn1 N2 . . 99.53(18) n
    N5 Mn1 N3 . . 98.1(2) n
    N6 Mn1 N3 . . 103.71(18) n
    N2 Mn1 N3 . . 73.15(16) n
    N5 Mn1 N4 . . 86.78(19) n
    N6 Mn1 N4 . . 85.41(17) n
    N2 Mn1 N4 . . 142.80(16) n
    N3 Mn1 N4 . . 69.88(16) n
    N5 Mn1 N1 . . 82.92(18) n
    N6 Mn1 N1 . . 89.82(17) n
    N2 Mn1 N1 . . 69.50(15) n
    N3 Mn1 N1 . . 141.88(17) n
    N4 Mn1 N1 . . 147.69(16) n
    C1 N1 C5 . . 117.9(5) ?
    C1 N1 Mn1 . . 125.2(4) ?
    C5 N1 Mn1 . . 116.7(3) ?
    C6 N2 C8 . . 121.8(5) ?
    C6 N2 Mn1 . . 122.4(4) ?
    C8 N2 Mn1 . . 115.5(3) ?
    C11 N3 C10 . . 122.6(5) ?
    C11 N3 Mn1 . . 122.1(4) ?
    C10 N3 Mn1 . . 114.9(3) ?
    C17 N4 C13 . . 117.9(5) ?
    C17 N4 Mn1 . . 125.7(4) ?
    C13 N4 Mn1 . . 116.3(3) ?
    C18 N5 Mn1 . . 169.2(6) ?
    C19 N6 Mn1 . . 174.9(5) ?
    N1 C1 C2 . . 123.6(6) ?
    N1 C1 H1 . . 118.2 ?
    C2 C1 H1 . . 118.2 ?
    C3 C2 C1 . . 118.0(6) ?
    C3 C2 H2 . . 121.0 ?
    C1 C2 H2 . . 121.0 ?
    C2 C3 C4 . . 119.7(6) ?
    C2 C3 H3 . . 120.1 ?
    C4 C3 H3 . . 120.1 ?
    C3 C4 C5 . . 119.2(6) ?
    C3 C4 H4 . . 120.4 ?
    C5 C4 H4 . . 120.4 ?
    N1 C5 C4 . . 121.6(5) ?
    N1 C5 C6 . . 115.6(4) ?
    C4 C5 C6 . . 122.8(5) ?
    N2 C6 C5 . . 115.6(5) ?
    N2 C6 C7 . . 126.2(5) ?
    C5 C6 C7 . . 118.2(5) ?
    C6 C7 H7A . . 109.5 ?
    C6 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C6 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C10 C8 N2 . . 109.6(5) ?
    C10 C8 C9 . . 109.9(6) ?
    N2 C8 C9 . . 107.8(5) ?
    C10 C8 H8 . . 109.8 ?
    N2 C8 H8 . . 109.8 ?
    C9 C8 H8 . . 109.8 ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C8 C10 N3 . . 110.8(5) ?
    C8 C10 H10A . . 109.5 ?
    N3 C10 H10A . . 109.5 ?
    C8 C10 H10B . . 109.5 ?
    N3 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 108.1 ?
    N3 C11 C13 . . 115.4(5) ?
    N3 C11 C12 . . 125.6(5) ?
    C13 C11 C12 . . 118.9(5) ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    N4 C13 C14 . . 120.4(5) ?
    N4 C13 C11 . . 116.3(5) ?
    C14 C13 C11 . . 123.3(5) ?
    C15 C14 C13 . . 119.7(6) ?
    C15 C14 H14 . . 120.2 ?
    C13 C14 H14 . . 120.2 ?
    C16 C15 C14 . . 119.6(6) ?
    C16 C15 H15 . . 120.2 ?
    C14 C15 H15 . . 120.2 ?
    C15 C16 C17 . . 118.2(6) ?
    C15 C16 H16 . . 120.9 ?
    C17 C16 H16 . . 120.9 ?
    N4 C17 C16 . . 124.2(6) ?
    N4 C17 H17 . . 117.9 ?
    C16 C17 H17 . . 117.9 ?
    N5 C18 S1 . . 178.7(6) ?
    N6 C19 S2 . . 179.4(6) ?
