#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/46/2224646.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_2224646
loop_
_publ_author_name
'Wang, Cui-Juan'
'Zhou, Xian-Li'
'Zhang, Bing-Jun'
_publ_section_title
Aquaazido{3,3'-[o-phenylenebis(nitrilomethylidyne)]di-2-naphtholato}manganese(III)
_journal_coeditor_code           HB5265
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m50
_journal_paper_doi               10.1107/S1600536809052659
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Mn (C28 H18 N2 O2) (N3) (H2 O)]'
_chemical_formula_moiety         'C28 H20 Mn N5 O3'
_chemical_formula_sum            'C28 H20 Mn N5 O3'
_chemical_formula_weight         529.43
_chemical_name_systematic
;
Aquaazido{3,3'-[o-phenylenebis(nitrilomethylidyne)]di-2-
naphtholato}manganese(III)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.4550(10)
_cell_angle_beta                 97.6920(10)
_cell_angle_gamma                98.1800(10)
_cell_formula_units_Z            2
_cell_length_a                   6.68270(10)
_cell_length_b                   11.8803(2)
_cell_length_c                   15.3778(3)
_cell_measurement_reflns_used    4205
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      2.20
_cell_volume                     1176.49(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12984
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.02
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0348
_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)+(0.1000P)²+0.1339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                3519
_reflns_number_total             4205
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5265.cif
_cod_data_source_block           I
_cod_database_code               2224646
_cod_database_fobs_code          2224646
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.21230(5) 0.16035(2) 0.939323(19) 0.03163(14) Uani d . 1 . .
N N2 0.2571(3) 0.32332(14) 0.99968(12) 0.0311(4) Uani d . 1 . .
O O1 0.1336(2) 0.00645(12) 0.87811(10) 0.0356(4) Uani d . 1 . .
N N1 0.0823(3) 0.22059(14) 0.83821(12) 0.0307(4) Uani d . 1 . .
O O2 0.3187(2) 0.11226(12) 1.04281(10) 0.0378(4) Uani d . 1 . .
C C11 0.0019(3) 0.15759(19) 0.76023(15) 0.0337(5) Uani d . 1 . .
H H11 -0.0463 0.1971 0.7165 0.040 Uiso calc R 1 . .
O O3 -0.1107(2) 0.14771(13) 0.99088(12) 0.0411(4) Uani d D 1 . .
C C1 0.0450(3) -0.03427(17) 0.79550(14) 0.0303(5) Uani d . 1 . .
C C28 0.3879(3) 0.17238(18) 1.12325(14) 0.0322(5) Uani d . 1 . .
C C19 0.3971(3) 0.29292(19) 1.14745(14) 0.0339(5) Uani d . 1 . .
C C10 -0.0201(3) 0.03561(18) 0.73472(14) 0.0317(5) Uani d . 1 . .
C C16 0.2261(4) 0.51867(18) 0.96493(16) 0.0396(5) Uani d . 1 . .
H H16 0.2947 0.5559 1.0212 0.048 Uiso calc R 1 . .
C C18 0.3317(3) 0.36058(18) 1.08433(15) 0.0335(5) Uani d . 1 . .
H H18 0.3430 0.4396 1.1054 0.040 Uiso calc R 1 . .
N N3 0.5156(3) 0.19321(18) 0.89218(13) 0.0432(5) Uani d . 1 . .
C C22 0.5792(5) 0.5194(3) 1.35685(19) 0.0701(9) Uani d . 1 . .
H H22 0.5873 0.5986 1.3757 0.084 Uiso calc R 1 . .
C C25 0.5511(4) 0.2830(2) 1.30092(16) 0.0426(6) Uani d . 1 . .
C C12 0.0973(3) 0.34341(17) 0.85631(15) 0.0340(5) Uani d . 1 . .
C C9 -0.1130(3) -0.0194(2) 0.64364(15) 0.0369(5) Uani d . 1 . .
C C4 -0.1307(3) -0.1403(2) 0.61810(15) 0.0401(5) Uani d . 1 . .
C C5 -0.2167(4) -0.1956(2) 0.52954(17) 0.0526(7) Uani d . 1 . .
H H5 -0.2277 -0.2754 0.5134 0.063 Uiso calc R 1 . .
C C3 -0.0665(3) -0.20654(19) 0.68215(15) 0.0391(5) Uani d . 1 . .
H H3 -0.0817 -0.2865 0.6652 0.047 Uiso calc R 1 . .
C C2 0.0163(3) -0.15628(18) 0.76743(14) 0.0341(5) Uani d . 1 . .
H H2 0.0549 -0.2023 0.8081 0.041 Uiso calc R 1 . .
C C21 0.4955(4) 0.4698(2) 1.27051(18) 0.0534(7) Uani d . 1 . .
H H21 0.4480 0.5161 1.2318 0.064 Uiso calc R 1 . .
C C20 0.4797(3) 0.3504(2) 1.23912(15) 0.0388(5) Uani d . 1 . .
C C6 -0.2835(4) -0.1338(3) 0.46767(18) 0.0615(8) Uani d . 1 . .
H H6 -0.3387 -0.1706 0.4095 0.074 Uiso calc R 1 . .
C C14 0.0525(4) 0.5279(2) 0.82062(18) 0.0484(6) Uani d . 1 . .
H H14 0.0026 0.5718 0.7804 0.058 Uiso calc R 1 . .
C C15 0.1542(4) 0.58246(19) 0.90428(17) 0.0435(6) Uani d . 1 . .
H H15 0.1742 0.6628 0.9197 0.052 Uiso calc R 1 . .
C C26 0.5337(4) 0.1611(2) 1.27266(16) 0.0429(6) Uani d . 1 . .
H H26 0.5778 0.1170 1.3138 0.051 Uiso calc R 1 . .
C C13 0.0239(4) 0.4089(2) 0.79603(17) 0.0453(6) Uani d . 1 . .
H H13 -0.0441 0.3728 0.7394 0.054 Uiso calc R 1 . .
C C17 0.1963(3) 0.39877(17) 0.94229(14) 0.0323(5) Uani d . 1 . .
C C8 -0.1867(4) 0.0416(2) 0.57819(17) 0.0507(6) Uani d . 1 . .
H H8 -0.1800 0.1213 0.5932 0.061 Uiso calc R 1 . .
C C27 0.4558(3) 0.1080(2) 1.18858(15) 0.0383(5) Uani d . 1 . .
H H27 0.4460 0.0282 1.1727 0.046 Uiso calc R 1 . .
C C24 0.6383(4) 0.3370(3) 1.38941(17) 0.0570(7) Uani d . 1 . .
H H24 0.6868 0.2925 1.4294 0.068 Uiso calc R 1 . .
C C7 -0.2677(4) -0.0144(3) 0.49312(17) 0.0589(7) Uani d . 1 . .
H H7 -0.3134 0.0283 0.4512 0.071 Uiso calc R 1 . .
C C23 0.6525(5) 0.4530(3) 1.41707(19) 0.0712(9) Uani d . 1 . .
H H23 0.7105 0.4877 1.4754 0.085 Uiso calc R 1 . .
N N4 0.5327(3) 0.21532(17) 0.82123(15) 0.0454(5) Uani d . 1 . .
N N5 0.5512(4) 0.2366(3) 0.75124(19) 0.0928(10) Uani d . 1 . .
H H3WA -0.218(3) 0.149(3) 0.958(2) 0.139 Uiso d D 1 . .
H H3WB -0.129(6) 0.095(3) 1.019(2) 0.139 Uiso d 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
O2 Mn1 O1 . . 91.53(6) ?
O2 Mn1 N1 . . 173.78(7) ?
O1 Mn1 N1 . . 92.11(7) ?
O2 Mn1 N2 . . 92.48(7) ?
O1 Mn1 N2 . . 172.58(6) ?
N1 Mn1 N2 . . 83.37(7) ?
O2 Mn1 N3 . . 94.70(7) ?
O1 Mn1 N3 . . 96.71(7) ?
N1 Mn1 N3 . . 89.87(7) ?
N2 Mn1 N3 . . 89.18(7) ?
O2 Mn1 O3 . . 88.06(6) ?
O1 Mn1 O3 . . 88.87(6) ?
N1 Mn1 O3 . . 86.98(6) ?
N2 Mn1 O3 . . 85.04(6) ?
N3 Mn1 O3 . . 173.70(6) ?
C18 N2 C17 . . 122.21(18) ?
C18 N2 Mn1 . . 124.62(15) ?
C17 N2 Mn1 . . 113.16(13) ?
C1 O1 Mn1 . . 129.97(13) ?
C11 N1 C12 . . 122.49(18) ?
C11 N1 Mn1 . . 124.55(15) ?
C12 N1 Mn1 . . 112.82(14) ?
C28 O2 Mn1 . . 129.92(14) ?
N1 C11 C10 . . 127.3(2) ?
N1 C11 H11 . . 116.4 ?
C10 C11 H11 . . 116.4 ?
Mn1 O3 H3WA . . 122(3) ?
Mn1 O3 H3WB . . 112(3) ?
H3WA O3 H3WB . . 109(2) ?
O1 C1 C10 . . 123.96(18) ?
O1 C1 C2 . . 116.30(18) ?
C10 C1 C2 . . 119.74(18) ?
O2 C28 C19 . . 124.40(19) ?
O2 C28 C27 . . 115.74(19) ?
C19 C28 C27 . . 119.9(2) ?
C28 C19 C18 . . 121.72(19) ?
C28 C19 C20 . . 119.3(2) ?
C18 C19 C20 . . 119.0(2) ?
C1 C10 C11 . . 121.72(19) ?
C1 C10 C9 . . 119.03(19) ?
C11 C10 C9 . . 119.25(19) ?
C15 C16 C17 . . 120.1(2) ?
C15 C16 H16 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
N2 C18 C19 . . 126.8(2) ?
N2 C18 H18 . . 116.6 ?
C19 C18 H18 . . 116.6 ?
N4 N3 Mn1 . . 123.20(16) ?
C21 C22 C23 . . 121.1(3) ?
C21 C22 H22 . . 119.5 ?
C23 C22 H22 . . 119.5 ?
C24 C25 C20 . . 119.9(2) ?
C24 C25 C26 . . 120.8(2) ?
C20 C25 C26 . . 119.3(2) ?
C13 C12 C17 . . 119.66(19) ?
C13 C12 N1 . . 125.0(2) ?
C17 C12 N1 . . 115.35(18) ?
C4 C9 C8 . . 117.2(2) ?
C4 C9 C10 . . 119.0(2) ?
C8 C9 C10 . . 123.8(2) ?
C9 C4 C5 . . 120.2(2) ?
C9 C4 C3 . . 119.6(2) ?
C5 C4 C3 . . 120.2(2) ?
C6 C5 C4 . . 121.1(3) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C2 C3 C4 . . 121.7(2) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C3 C2 C1 . . 120.8(2) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C22 C21 C20 . . 121.4(3) ?
C22 C21 H21 . . 119.3 ?
C20 C21 H21 . . 119.3 ?
C21 C20 C25 . . 117.3(2) ?
C21 C20 C19 . . 124.1(2) ?
C25 C20 C19 . . 118.7(2) ?
C5 C6 C7 . . 118.8(2) ?
C5 C6 H6 . . 120.6 ?
C7 C6 H6 . . 120.6 ?
C15 C14 C13 . . 120.7(2) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C16 C15 C14 . . 120.3(2) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C27 C26 C25 . . 122.1(2) ?
C27 C26 H26 . . 119.0 ?
C25 C26 H26 . . 119.0 ?
C14 C13 C12 . . 119.7(2) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C16 C17 C12 . . 119.6(2) ?
C16 C17 N2 . . 125.5(2) ?
C12 C17 N2 . . 114.96(17) ?
C7 C8 C9 . . 121.1(2) ?
C7 C8 H8 . . 119.4 ?
C9 C8 H8 . . 119.4 ?
C26 C27 C28 . . 120.8(2) ?
C26 C27 H27 . . 119.6 ?
C28 C27 H27 . . 119.6 ?
C23 C24 C25 . . 121.1(3) ?
C23 C24 H24 . . 119.5 ?
C25 C24 H24 . . 119.5 ?
C8 C7 C6 . . 121.6(3) ?
C8 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
C24 C23 C22 . . 119.2(3) ?
C24 C23 H23 . . 120.4 ?
C22 C23 H23 . . 120.4 ?
N5 N4 N3 . . 179.3(3) ?
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 O2 . 1.8644(15) y
Mn1 O1 . 1.8799(14) y
Mn1 N1 . 1.9663(17) y
Mn1 N2 . 1.9672(17) y
Mn1 N3 . 2.2465(19) y
Mn1 O3 . 2.3905(16) y
N2 C18 . 1.309(3) ?
N2 C17 . 1.419(3) ?
O1 C1 . 1.309(2) ?
N1 C11 . 1.306(3) ?
N1 C12 . 1.426(3) ?
O2 C28 . 1.310(3) ?
C11 C10 . 1.419(3) ?
C11 H11 . 0.9300 ?
O3 H3WA . 0.824(10) ?
O3 H3WB . 0.82(3) ?
C1 C10 . 1.414(3) ?
C1 C2 . 1.420(3) ?
C28 C19 . 1.409(3) ?
C28 C27 . 1.425(3) ?
C19 C18 . 1.422(3) ?
C19 C20 . 1.458(3) ?
C10 C9 . 1.458(3) ?
C16 C15 . 1.375(3) ?
C16 C17 . 1.388(3) ?
C16 H16 . 0.9300 ?
C18 H18 . 0.9300 ?
N3 N4 . 1.180(3) ?
C22 C21 . 1.369(4) ?
C22 C23 . 1.396(4) ?
C22 H22 . 0.9300 ?
C25 C24 . 1.413(3) ?
C25 C20 . 1.417(3) ?
C25 C26 . 1.425(4) ?
C12 C13 . 1.389(3) ?
C12 C17 . 1.405(3) ?
C9 C4 . 1.409(3) ?
C9 C8 . 1.411(3) ?
C4 C5 . 1.416(3) ?
C4 C3 . 1.418(3) ?
C5 C6 . 1.361(4) ?
C5 H5 . 0.9300 ?
C3 C2 . 1.355(3) ?
C3 H3 . 0.9300 ?
C2 H2 . 0.9300 ?
C21 C20 . 1.405(3) ?
C21 H21 . 0.9300 ?
C6 C7 . 1.393(4) ?
C6 H6 . 0.9300 ?
C14 C15 . 1.380(4) ?
C14 C13 . 1.381(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C26 C27 . 1.341(3) ?
C26 H26 . 0.9300 ?
C13 H13 . 0.9300 ?
C8 C7 . 1.367(4) ?
C8 H8 . 0.9300 ?
C27 H27 . 0.9300 ?
C24 C23 . 1.359(4) ?
C24 H24 . 0.9300 ?
C7 H7 . 0.9300 ?
C23 H23 . 0.9300 ?
N4 N5 . 1.163(3) ?
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
O3 H3WA N3 1_455 0.824(10) 2.10(3) 2.911(3) 167(4)
O3 H3WB O1 2_557 0.82(3) 2.14(3) 2.941(2) 164(4)
O3 H3WB O2 2_557 0.82(3) 2.57(3) 3.130(2) 127(3)
