#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/84/2228463.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_2228463
loop_
_publ_author_name
'Zhang, Daopeng'
_publ_section_title
;
 Monoclinic form of
 (cyanato-κN){2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-κ⁴O,N,N',O'}manganese(III)
;
_journal_coeditor_code           LH5164
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1656
_journal_paper_doi               10.1107/S1600536810048270
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Mn (C16 H14 N2 O2) (N C O)]'
_chemical_formula_moiety         'C17 H14 Mn N3 O3'
_chemical_formula_sum            'C17 H14 Mn N3 O3'
_chemical_formula_weight         363.25
_chemical_name_systematic
;
(cyanato-κN){2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-
κ⁴O,N,N',O'}manganese(III)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 97.826(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6399(16)
_cell_length_b                   10.9133(18)
_cell_length_c                   15.198(3)
_cell_measurement_reflns_used    1289
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.621
_cell_measurement_theta_min      2.579
_cell_volume                     1584.0(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD 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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7377
_diffrn_reflns_theta_full        24.74
_diffrn_reflns_theta_max         24.74
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  0.8279
_exptl_absorpt_correction_T_min  0.7430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            dark-brown
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0695P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                1769
_reflns_number_total             2698
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5164.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      ' P21/n'
_cod_database_code               2228463
_cod_database_fobs_code          2228463
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'
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_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'
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) ?
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 ?
