#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/09/2230930.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_2230930
loop_
_publ_author_name
'Suleiman Gwaram, Nura'
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
_publ_section_title
;
 Aqua{2-(morpholin-4-yl)-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³N,N',N''}bis(thiocyanato-κN)manganese(II)
;
_journal_coeditor_code           XU5237
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m928
_journal_paper_doi               10.1107/S1600536811022124
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Mn (N C S)2 (C13 H19 N3 O) (H2 O)]'
_chemical_formula_moiety         'C15 H21 Mn N5 O2 S2'
_chemical_formula_sum            'C15 H21 Mn N5 O2 S2'
_chemical_formula_weight         422.43
_chemical_name_systematic
;
Aqua{2-(morpholin-4-yl)-N-[1-(2-pyridyl)ethylidene]ethanamine-
κ³N,N',N''}bis(thiocyanato-κN)manganese(II)
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.149(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1837(13)
_cell_length_b                   22.408(4)
_cell_length_c                   12.112(2)
_cell_measurement_reflns_used    2405
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.48
_cell_volume                     1949.3(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11816
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  0.9308
_exptl_absorpt_correction_T_min  0.8462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.463
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4235
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0302P)²+0.8463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                3197
_reflns_number_total             4235
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5237.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230930
_cod_database_fobs_code          2230930
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn Mn1 0.32353(4) 0.376455(15) 0.71236(3) 0.01469(10) Uani d . 1 1 . .
S S1 -0.15046(9) 0.22409(3) 0.71859(8) 0.0455(2) Uani d . 1 1 . .
S S2 0.08739(9) 0.56599(3) 0.84034(6) 0.03342(18) Uani d U 1 1 . .
O O1 0.3684(2) 0.29611(7) 1.04053(13) 0.0274(4) Uani d . 1 1 . .
O O2 0.4538(2) 0.28777(8) 0.69253(14) 0.0240(4) Uani d D 1 1 . .
H H2A 0.562(3) 0.2763(11) 0.701(2) 0.029 Uiso d D 1 1 . .
H H2B 0.406(3) 0.2628(10) 0.6508(19) 0.029 Uiso d D 1 1 . .
N N1 0.3511(2) 0.38231(8) 0.52518(15) 0.0193(4) Uani d . 1 1 . .
N N2 0.5890(2) 0.42204(8) 0.67754(15) 0.0167(4) Uani d . 1 1 . .
N N3 0.4725(2) 0.38883(8) 0.88902(15) 0.0159(4) Uani d . 1 1 . .
N N4 0.0713(3) 0.32585(10) 0.71154(18) 0.0291(5) Uani d . 1 1 . .
N N5 0.1827(3) 0.45968(9) 0.73672(16) 0.0216(4) Uani d . 1 1 . .
C C1 0.2350(3) 0.35789(11) 0.4504(2) 0.0263(6) Uani d . 1 1 . .
H H1 0.1197 0.3424 0.4745 0.032 Uiso calc R 1 1 . .
C C2 0.2752(4) 0.35409(12) 0.3394(2) 0.0341(6) Uani d . 1 1 . .
H H2 0.1883 0.3371 0.2883 0.041 Uiso calc R 1 1 . .
C C3 0.4436(4) 0.37543(13) 0.3045(2) 0.0375(7) Uani d . 1 1 . .
H H3 0.4762 0.3724 0.2291 0.045 Uiso calc R 1 1 . .
C C4 0.5648(4) 0.40130(12) 0.3805(2) 0.0305(6) Uani d . 1 1 . .
H H4 0.6811 0.4167 0.3578 0.037 Uiso calc R 1 1 . .
C C5 0.5147(3) 0.40447(10) 0.49019(19) 0.0199(5) Uani d . 1 1 . .
C C6 0.6389(3) 0.43017(11) 0.57811(19) 0.0206(5) Uani d . 1 1 . .
C C7 0.8112(3) 0.46256(13) 0.5449(2) 0.0345(7) Uani d . 1 1 . .
H H7A 0.8537 0.4885 0.6054 0.052 Uiso calc R 1 1 . .
H H7B 0.7838 0.4868 0.4791 0.052 Uiso calc R 1 1 . .
H H7C 0.9089 0.4336 0.5283 0.052 Uiso calc R 1 1 . .
C C8 0.6995(3) 0.44329(11) 0.77211(19) 0.0217(5) Uani d . 1 1 . .
H H8A 0.7483 0.4837 0.7568 0.026 Uiso calc R 1 1 . .
H H8B 0.8065 0.4163 0.7858 0.026 Uiso calc R 1 1 . .
C C9 0.5774(3) 0.44504(10) 0.87324(19) 0.0197(5) Uani d . 1 1 . .
H H9A 0.6566 0.4526 0.9396 0.024 Uiso calc R 1 1 . .
H H9B 0.4882 0.4785 0.8656 0.024 Uiso calc R 1 1 . .
C C10 0.6016(3) 0.34062(10) 0.92493(19) 0.0209(5) Uani d . 1 1 . .
H H10A 0.6755 0.3543 0.9900 0.025 Uiso calc R 1 1 . .
H H10B 0.6889 0.3319 0.8649 0.025 Uiso calc R 1 1 . .
C C11 0.4980(3) 0.28452(11) 0.95414(19) 0.0250(6) Uani d . 1 1 . .
H H11A 0.4299 0.2694 0.8880 0.030 Uiso calc R 1 1 . .
H H11B 0.5877 0.2535 0.9788 0.030 Uiso calc R 1 1 . .
C C12 0.2375(3) 0.34069(11) 1.0051(2) 0.0245(5) Uani d . 1 1 . .
H H12A 0.1470 0.3480 1.0642 0.029 Uiso calc R 1 1 . .
H H12B 0.1681 0.3265 0.9388 0.029 Uiso calc R 1 1 . .
C C13 0.3372(3) 0.39803(10) 0.97860(19) 0.0209(5) Uani d . 1 1 . .
H H13A 0.2450 0.4286 0.9555 0.025 Uiso calc R 1 1 . .
H H13B 0.4037 0.4128 1.0456 0.025 Uiso calc R 1 1 . .
C C14 -0.0226(3) 0.28415(11) 0.7138(2) 0.0227(5) Uani d . 1 1 . .
C C15 0.1420(3) 0.50395(10) 0.78071(18) 0.0158(4) Uani d U 1 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'
Mn Mn 0.3368 0.7283 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N4 Mn1 N5 . . 93.43(8) ?
N4 Mn1 N2 . . 168.07(8) ?
N5 Mn1 N2 . . 92.03(7) ?
N4 Mn1 O2 . . 83.30(7) ?
N5 Mn1 O2 . . 176.33(7) ?
N2 Mn1 O2 . . 91.49(7) ?
N4 Mn1 N1 . . 96.67(8) ?
N5 Mn1 N1 . . 97.88(7) ?
N2 Mn1 N1 . . 72.05(7) ?
O2 Mn1 N1 . . 84.17(7) ?
N4 Mn1 N3 . . 115.48(7) ?
N5 Mn1 N3 . . 88.85(7) ?
N2 Mn1 N3 . . 75.21(6) ?
O2 Mn1 N3 . . 91.07(6) ?
N1 Mn1 N3 . . 146.75(7) ?
C12 O1 C11 . . 109.80(17) ?
Mn1 O2 H2A . . 132.0(19) ?
Mn1 O2 H2B . . 120.5(19) ?
H2A O2 H2B . . 104(3) ?
C1 N1 C5 . . 118.2(2) ?
C1 N1 Mn1 . . 125.76(16) ?
C5 N1 Mn1 . . 115.18(14) ?
C6 N2 C8 . . 122.36(19) ?
C6 N2 Mn1 . . 120.36(15) ?
C8 N2 Mn1 . . 117.27(13) ?
C9 N3 C10 . . 109.89(17) ?
C9 N3 C13 . . 108.54(17) ?
C10 N3 C13 . . 107.53(17) ?
C9 N3 Mn1 . . 101.71(12) ?
C10 N3 Mn1 . . 116.38(13) ?
C13 N3 Mn1 . . 112.49(14) ?
C14 N4 Mn1 . . 157.83(19) ?
C15 N5 Mn1 . . 157.80(18) ?
N1 C1 C2 . . 123.0(2) ?
N1 C1 H1 . . 118.5 ?
C2 C1 H1 . . 118.5 ?
C3 C2 C1 . . 118.6(2) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C2 C3 C4 . . 119.2(2) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C3 C4 C5 . . 119.2(2) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
N1 C5 C4 . . 121.8(2) ?
N1 C5 C6 . . 115.45(19) ?
C4 C5 C6 . . 122.8(2) ?
N2 C6 C5 . . 116.3(2) ?
N2 C6 C7 . . 124.9(2) ?
C5 C6 C7 . . 118.8(2) ?
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 ?
N2 C8 C9 . . 109.09(17) ?
N2 C8 H8A . . 109.9 ?
C9 C8 H8A . . 109.9 ?
N2 C8 H8B . . 109.9 ?
C9 C8 H8B . . 109.9 ?
H8A C8 H8B . . 108.3 ?
N3 C9 C8 . . 112.62(18) ?
N3 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
N3 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.8 ?
N3 C10 C11 . . 111.58(19) ?
N3 C10 H10A . . 109.3 ?
C11 C10 H10A . . 109.3 ?
N3 C10 H10B . . 109.3 ?
C11 C10 H10B . . 109.3 ?
H10A C10 H10B . . 108.0 ?
O1 C11 C10 . . 110.50(19) ?
O1 C11 H11A . . 109.6 ?
C10 C11 H11A . . 109.6 ?
O1 C11 H11B . . 109.6 ?
C10 C11 H11B . . 109.6 ?
H11A C11 H11B . . 108.1 ?
O1 C12 C13 . . 110.3(2) ?
O1 C12 H12A . . 109.6 ?
C13 C12 H12A . . 109.6 ?
O1 C12 H12B . . 109.6 ?
C13 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
N3 C13 C12 . . 110.95(18) ?
N3 C13 H13A . . 109.4 ?
C12 C13 H13A . . 109.4 ?
N3 C13 H13B . . 109.4 ?
C12 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
N4 C14 S1 . . 178.4(2) ?
N5 C15 S2 . . 179.1(2) ?
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 N1 . 2.2835(19) y
Mn1 N2 . 2.2115(18) y
Mn1 N3 . 2.3891(19) y
Mn1 N4 . 2.137(2) y
Mn1 N5 . 2.145(2) y
Mn1 O2 . 2.2117(17) y
S1 C14 . 1.631(2) ?
S2 C15 . 1.618(2) ?
O1 C12 . 1.432(3) ?
O1 C11 . 1.438(3) ?
O2 H2A . 0.820(16) ?
O2 H2B . 0.824(16) ?
N1 C1 . 1.336(3) ?
N1 C5 . 1.352(3) ?
N2 C6 . 1.276(3) ?
N2 C8 . 1.460(3) ?
N3 C9 . 1.482(3) ?
N3 C10 . 1.483(3) ?
N3 C13 . 1.486(3) ?
N4 C14 . 1.153(3) ?
N5 C15 . 1.166(3) ?
C1 C2 . 1.384(4) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.375(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.382(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.386(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.491(3) ?
C6 C7 . 1.497(3) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 C9 . 1.521(3) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.507(3) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.509(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
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
O2 H2A S1 1_655 0.820(16) 2.382(17) 3.1910(18) 169(2)
O2 H2B O1 4_565 0.824(16) 1.893(18) 2.693(2) 164(3)
C11 H11A O2 . 0.99 2.41 3.179(3) 134
C12 H12A S2 3_567 0.99 2.82 3.674(2) 145
