##############################################################################
###                                                                        ###
###        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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(cyanato-κN){2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-
κ⁴O,N,N',O'}manganese(III)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H14 Mn N3 O3'
_chemical_formula_sum     'C17 H14 Mn N3 O3'
_chemical_formula_iupac     '[Mn (C16 H14 N2 O2) (N C O)]'
_chemical_formula_weight     363.25
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     ' P21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     9.6399(16)
_cell_length_b     10.9133(18)
_cell_length_c     15.198(3)
_cell_angle_alpha     90.00
_cell_angle_beta     97.826(3)
_cell_angle_gamma     90.00
_cell_volume     1584.0(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1289
_cell_measurement_theta_min     2.579
_cell_measurement_theta_max     26.621
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     dark-brown
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.23
_exptl_crystal_density_diffrn     1.523
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     744
_exptl_absorpt_coefficient_mu     0.854
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.7430
_exptl_absorpt_correction_T_max     0.8279
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7377
_diffrn_reflns_av_R_equivalents     0.0465
_diffrn_reflns_av_sigmaI/netI     0.0564
_diffrn_reflns_theta_min     2.30
_diffrn_reflns_theta_max     24.74
_diffrn_reflns_theta_full     24.74
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     ?
_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     2698
_reflns_number_gt     1769
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0853
_refine_ls_R_factor_gt     0.0480
_refine_ls_wR_factor_gt     0.1134
_refine_ls_wR_factor_ref     0.1312
_refine_ls_goodness_of_fit_ref     1.012
_refine_ls_restrained_S_all     1.012
_refine_ls_number_reflns     2698
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0695P)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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.529
_refine_diff_density_min     -0.327
_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'
    '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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2001)'
_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 0.10463(6) 0.63253(5) 0.52050(4) 0.0420(2) Uani d . 1 . .
    O O1 -0.0313(3) 0.7121(2) 0.57698(17) 0.0489(7) Uani d . 1 . .
    O O2 0.1015(3) 0.4886(2) 0.58923(17) 0.0472(7) Uani d . 1 . .
    O O3 0.5003(4) 0.6657(5) 0.6799(3) 0.1254(17) Uani d . 1 . .
    N N1 0.0793(3) 0.7500(3) 0.4211(2) 0.0453(8) Uani d . 1 . .
    N N2 0.2150(3) 0.5430(3) 0.4394(2) 0.0425(8) Uani d . 1 . .
    N N3 0.2893(4) 0.7093(3) 0.5904(2) 0.0566(10) Uani d . 1 . .
    C C1 -0.1070(4) 0.8699(4) 0.4711(3) 0.0476(10) Uani d . 1 . .
    C C2 -0.1116(4) 0.8071(4) 0.5515(3) 0.0463(10) Uani d . 1 . .
    C C3 -0.2089(5) 0.8453(4) 0.6060(3) 0.0621(13) Uani d . 1 . .
    H H3 -0.2123 0.8054 0.6598 0.075 Uiso calc R 1 . .
    C C4 -0.2991(5) 0.9395(4) 0.5824(4) 0.0715(14) Uani d . 1 . .
    H H4 -0.3638 0.9619 0.6196 0.086 Uiso calc R 1 . .
    C C5 -0.2956(5) 1.0021(4) 0.5037(4) 0.0724(15) Uani d . 1 . .
    H H5 -0.3568 1.0667 0.4879 0.087 Uiso calc R 1 . .
    C C6 -0.2003(4) 0.9674(4) 0.4492(3) 0.0605(12) Uani d . 1 . .
    H H6 -0.1974 1.0096 0.3963 0.073 Uiso calc R 1 . .
    C C7 -0.0106(4) 0.8380(4) 0.4105(3) 0.0530(11) Uani d . 1 . .
    H H7 -0.0132 0.8849 0.3593 0.064 Uiso calc R 1 . .
    C C8 0.3143(4) 0.3997(3) 0.5504(3) 0.0415(9) Uani d . 1 . .
    C C9 0.2170(4) 0.4207(4) 0.6109(3) 0.0423(9) Uani d . 1 . .
    C C10 0.2394(4) 0.3634(4) 0.6929(3) 0.0503(10) Uani d . 1 . .
    H H10 0.1770 0.3776 0.7334 0.060 Uiso calc R 1 . .
    C C11 0.3501(4) 0.2868(4) 0.7163(3) 0.0626(13) Uani d . 1 . .
    H H11 0.3630 0.2503 0.7721 0.075 Uiso calc R 1 . .
    C C12 0.4445(4) 0.2632(4) 0.6557(3) 0.0638(13) Uani d . 1 . .
    H H12 0.5195 0.2103 0.6709 0.077 Uiso calc R 1 . .
    C C13 0.4252(4) 0.3189(4) 0.5740(3) 0.0524(11) Uani d . 1 . .
    H H13 0.4872 0.3025 0.5337 0.063 Uiso calc R 1 . .
    C C14 0.2980(4) 0.4541(4) 0.4634(3) 0.0451(10) Uani d . 1 . .
    H H14 0.3511 0.4225 0.4220 0.054 Uiso calc R 1 . .
    C C15 0.1771(4) 0.7294(4) 0.3564(3) 0.0569(12) Uani d . 1 . .
    H H15A 0.2662 0.7686 0.3763 0.068 Uiso calc R 1 . .
    H H15B 0.1395 0.7634 0.2992 0.068 Uiso calc R 1 . .
    C C16 0.1964(4) 0.5929(4) 0.3489(3) 0.0533(11) Uani d . 1 . .
    H H16A 0.1150 0.5565 0.3141 0.064 Uiso calc R 1 . .
    H H16B 0.2780 0.5752 0.3201 0.064 Uiso calc R 1 . .
    C C17 0.3891(6) 0.6904(5) 0.6329(3) 0.0659(14) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Mn1 0.0320(4) 0.0509(4) 0.0445(4) 0.0037(3) 0.0098(3) 0.0052(3)
    O1 0.0417(16) 0.0560(18) 0.0502(17) 0.0124(14) 0.0108(13) 0.0024(13)
    O2 0.0324(16) 0.0555(17) 0.0570(19) 0.0080(13) 0.0174(13) 0.0130(13)
    O3 0.051(2) 0.238(5) 0.081(3) 0.023(3) -0.012(2) -0.046(3)
    N1 0.0299(18) 0.057(2) 0.049(2) 0.0001(16) 0.0062(15) 0.0068(16)
    N2 0.0301(18) 0.057(2) 0.042(2) 0.0001(16) 0.0086(14) 0.0047(16)
    N3 0.043(2) 0.065(3) 0.059(3) -0.0037(19) 0.0009(19) -0.0029(19)
    C1 0.034(2) 0.045(2) 0.063(3) -0.003(2) 0.0041(19) 0.001(2)
    C2 0.035(2) 0.046(2) 0.057(3) -0.001(2) 0.004(2) -0.010(2)
    C3 0.056(3) 0.063(3) 0.069(3) 0.008(2) 0.015(2) -0.007(2)
    C4 0.053(3) 0.068(3) 0.095(4) 0.014(3) 0.014(3) -0.007(3)
    C5 0.052(3) 0.054(3) 0.109(5) 0.015(2) 0.003(3) -0.006(3)
    C6 0.044(3) 0.056(3) 0.080(3) 0.002(2) 0.001(2) 0.011(2)
    C7 0.038(2) 0.060(3) 0.059(3) -0.007(2) -0.001(2) 0.016(2)
    C8 0.028(2) 0.050(2) 0.048(2) -0.0009(17) 0.0096(17) -0.0012(19)
    C9 0.030(2) 0.048(2) 0.049(3) -0.0021(18) 0.0077(18) 0.0004(19)
    C10 0.034(2) 0.068(3) 0.049(3) 0.000(2) 0.0102(18) 0.005(2)
    C11 0.040(3) 0.087(4) 0.059(3) 0.008(2) 0.004(2) 0.023(3)
    C12 0.034(3) 0.080(3) 0.078(3) 0.011(2) 0.008(2) 0.016(3)
    C13 0.028(2) 0.065(3) 0.066(3) 0.000(2) 0.013(2) 0.003(2)
    C14 0.026(2) 0.059(3) 0.052(3) -0.0040(19) 0.0122(18) -0.006(2)
    C15 0.040(3) 0.081(3) 0.051(3) 0.008(2) 0.013(2) 0.022(2)
    C16 0.039(2) 0.085(3) 0.037(2) 0.003(2) 0.0105(18) 0.005(2)
    C17 0.048(3) 0.100(4) 0.054(3) -0.013(3) 0.021(3) -0.029(3)
_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 O1 . 1.874(2) ?
    Mn1 O2 . 1.889(3) ?
    Mn1 N1 . 1.971(3) ?
    Mn1 N2 . 1.991(3) ?
    Mn1 N3 . 2.118(4) ?
    O1 C2 . 1.320(4) ?
    O2 C9 . 1.340(4) ?
    O3 C17 . 1.235(6) ?
    N1 C7 . 1.288(5) ?
    N1 C15 . 1.469(5) ?
    N2 C14 . 1.280(5) ?
    N2 C16 . 1.466(5) ?
    N3 C17 . 1.102(6) ?
    C1 C6 . 1.403(5) ?
    C1 C2 . 1.408(5) ?
    C1 C7 . 1.437(6) ?
    C2 C3 . 1.397(5) ?
    C3 C4 . 1.363(6) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.382(7) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.371(6) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 C13 . 1.394(5) ?
    C8 C9 . 1.418(5) ?
    C8 C14 . 1.438(5) ?
    C9 C10 . 1.386(5) ?
    C10 C11 . 1.364(5) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.403(6) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.372(5) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.508(6) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
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 O2 . . 93.85(11) ?
    O1 Mn1 N1 . . 91.64(12) ?
    O2 Mn1 N1 . . 162.75(13) ?
    O1 Mn1 N2 . . 167.59(13) ?
    O2 Mn1 N2 . . 89.12(12) ?
    N1 Mn1 N2 . . 82.24(13) ?
    O1 Mn1 N3 . . 100.33(13) ?
    O2 Mn1 N3 . . 97.30(13) ?
    N1 Mn1 N3 . . 97.78(14) ?
    N2 Mn1 N3 . . 91.22(14) ?
    C2 O1 Mn1 . . 130.4(2) ?
    C9 O2 Mn1 . . 121.3(2) ?
    C7 N1 C15 . . 120.9(3) ?
    C7 N1 Mn1 . . 126.2(3) ?
    C15 N1 Mn1 . . 112.9(2) ?
    C14 N2 C16 . . 122.7(3) ?
    C14 N2 Mn1 . . 124.2(3) ?
    C16 N2 Mn1 . . 113.0(2) ?
    C17 N3 Mn1 . . 145.7(4) ?
    C6 C1 C2 . . 118.7(4) ?
    C6 C1 C7 . . 118.8(4) ?
    C2 C1 C7 . . 122.5(4) ?
    O1 C2 C3 . . 118.3(4) ?
    O1 C2 C1 . . 123.4(3) ?
    C3 C2 C1 . . 118.2(4) ?
    C4 C3 C2 . . 121.6(5) ?
    C4 C3 H3 . . 119.2 ?
    C2 C3 H3 . . 119.2 ?
    C3 C4 C5 . . 120.8(5) ?
    C3 C4 H4 . . 119.6 ?
    C5 C4 H4 . . 119.6 ?
    C6 C5 C4 . . 118.9(4) ?
    C6 C5 H5 . . 120.5 ?
    C4 C5 H5 . . 120.5 ?
    C5 C6 C1 . . 121.8(5) ?
    C5 C6 H6 . . 119.1 ?
    C1 C6 H6 . . 119.1 ?
    N1 C7 C1 . . 125.7(4) ?
    N1 C7 H7 . . 117.1 ?
    C1 C7 H7 . . 117.1 ?
    C13 C8 C9 . . 119.1(4) ?
    C13 C8 C14 . . 118.8(3) ?
    C9 C8 C14 . . 122.0(3) ?
    O2 C9 C10 . . 119.5(3) ?
    O2 C9 C8 . . 122.1(3) ?
    C10 C9 C8 . . 118.3(4) ?
    C11 C10 C9 . . 122.1(4) ?
    C11 C10 H10 . . 119.0 ?
    C9 C10 H10 . . 119.0 ?
    C10 C11 C12 . . 119.8(4) ?
    C10 C11 H11 . . 120.1 ?
    C12 C11 H11 . . 120.1 ?
    C13 C12 C11 . . 119.5(4) ?
    C13 C12 H12 . . 120.3 ?
    C11 C12 H12 . . 120.3 ?
    C12 C13 C8 . . 121.2(4) ?
    C12 C13 H13 . . 119.4 ?
    C8 C13 H13 . . 119.4 ?
    N2 C14 C8 . . 124.2(3) ?
    N2 C14 H14 . . 117.9 ?
    C8 C14 H14 . . 117.9 ?
    N1 C15 C16 . . 107.4(3) ?
    N1 C15 H15A . . 110.2 ?
    C16 C15 H15A . . 110.2 ?
    N1 C15 H15B . . 110.2 ?
    C16 C15 H15B . . 110.2 ?
    H15A C15 H15B . . 108.5 ?
    N2 C16 C15 . . 107.2(3) ?
    N2 C16 H16A . . 110.3 ?
    C15 C16 H16A . . 110.3 ?
    N2 C16 H16B . . 110.3 ?
    C15 C16 H16B . . 110.3 ?
    H16A C16 H16B . . 108.5 ?
    N3 C17 O3 . . 178.2(6) ?
data_global
_journal_date_recd_electronic     2010-11-14
_journal_date_accepted     2010-11-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     12
_journal_page_first     m1656
_journal_page_last     m1656
_journal_paper_category     QM
_journal_coeditor_code     LH5164
_publ_contact_author_name     'Daopeng Zhang'
_publ_contact_author_address
;
College of Chemical Engineering, Shandong University of Technology,
Zibo 255049, China
;
_publ_contact_author_email     dpzhang73@126.com
_publ_contact_author_Phone     ?
_publ_section_title
;\
Monoclinic form of
(cyanato-κN){2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-\
κ⁴O,N,N',O'}manganese(III)
;
loop_
    _publ_author_name
    _publ_author_address
    'Daopeng Zhang'
;
College of Chemical Engineering, Shandong University of Technology,
Zibo 255049, People's Republic of China
;
