#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/97/2219759.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_2219759
loop_
_publ_author_name
'Wang, Feng'
'Zhang, Jianming'
'Wang, Qirong'
'Huang, Shiying'
_publ_section_title
;Bis(N,N-dimethylformamide-κO)bis(1-methylimidazole-2-carbaldehyde
 oximato-κ²N,O)manganese(III) perchlorate
;
_journal_coeditor_code           AT2654
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1462
_journal_paper_doi               10.1107/S1600536808034016
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Mn (C5 H6 N3 O)2 (C3 H7 N O)] Cl O4'
_chemical_formula_moiety         'C16 H26 Mn N8 O4 +, Cl O4 -'
_chemical_formula_sum            'C16 H26 Cl Mn N8 O8'
_chemical_formula_weight         548.84
_chemical_name_systematic
;
Bis(N,N-dimethylformamide-\kO)bis(1-methylimidazole-2-
carbaldehyde oximato-κ²N,O)manganese(III) perchlorate
;
_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                82.841(10)
_cell_angle_beta                 85.273(11)
_cell_angle_gamma                80.471(16)
_cell_formula_units_Z            2
_cell_length_a                   7.6158(11)
_cell_length_b                   12.324(2)
_cell_length_c                   12.8600(16)
_cell_measurement_reflns_used    2239
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      2.46
_cell_volume                     1178.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (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      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART 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  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9397
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.9304
_exptl_absorpt_correction_T_min  0.8497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block '
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0845P)²+0.2454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1578
_reflns_number_gt                3191
_reflns_number_total             4101
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2654.cif
_cod_data_source_block           I
_cod_database_code               2219759
_cod_database_fobs_code          2219759
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
Mn Mn1 0.67156(7) 0.67997(4) 0.75744(4) 0.0366(2) Uani d . 1
C C1 0.3414(5) 0.8512(4) 0.7017(3) 0.0513(11) Uani d . 1
H H1 0.2579 0.8049 0.7250 0.062 Uiso calc R 1
C C2 0.3042(6) 0.9582(4) 0.6627(3) 0.0579(12) Uani d . 1
H H2 0.1912 0.9989 0.6537 0.070 Uiso calc R 1
C C3 0.5955(6) 0.9116(3) 0.6626(3) 0.0446(10) Uani d . 1
C C4 0.4845(7) 1.1121(3) 0.5958(4) 0.0667(14) Uani d . 1
H H4A 0.5257 1.1481 0.6491 0.100 Uiso calc R 1
H H4B 0.3719 1.1521 0.5742 0.100 Uiso calc R 1
H H4C 0.5699 1.1104 0.5366 0.100 Uiso calc R 1
C C5 0.7840(6) 0.9159(4) 0.6449(3) 0.0529(11) Uani d . 1
H H5 0.8146 0.9804 0.6076 0.063 Uiso calc R 1
C C6 0.9974(5) 0.5219(3) 0.8403(3) 0.0389(9) Uani d . 1
H H6 1.0818 0.5646 0.8096 0.047 Uiso calc R 1
C C7 1.0311(5) 0.4261(3) 0.9042(3) 0.0415(9) Uani d . 1
H H7 1.1425 0.3912 0.9251 0.050 Uiso calc R 1
C C8 0.7428(5) 0.4639(3) 0.8846(3) 0.0358(9) Uani d . 1
C C9 0.8461(6) 0.2892(3) 1.0015(3) 0.0533(11) Uani d . 1
H H9A 0.7266 0.2973 1.0330 0.080 Uiso calc R 1
H H9B 0.9294 0.2769 1.0555 0.080 Uiso calc R 1
H H9C 0.8660 0.2272 0.9612 0.080 Uiso calc R 1
C C10 0.5576(5) 0.4523(3) 0.8923(3) 0.0462(10) Uani d . 1
H H10 0.5274 0.3893 0.9328 0.055 Uiso calc R 1
C C11 0.6945(5) 0.8367(3) 0.9405(3) 0.0431(10) Uani d . 1
H H11 0.7584 0.8692 0.8836 0.052 Uiso calc R 1
C C12 0.7615(6) 0.9785(4) 1.0387(3) 0.0573(12) Uani d . 1
H H12A 0.8234 1.0007 0.9734 0.086 Uiso calc R 1
H H12B 0.8445 0.9599 1.0928 0.086 Uiso calc R 1
H H12C 0.6711 1.0384 1.0570 0.086 Uiso calc R 1
C C13 0.5781(6) 0.8394(4) 1.1206(3) 0.0624(13) Uani d . 1
H H13A 0.5095 0.7868 1.1020 0.094 Uiso calc R 1
H H13B 0.4993 0.8994 1.1488 0.094 Uiso calc R 1
H H13C 0.6591 0.8038 1.1724 0.094 Uiso calc R 1
C C14 0.7324(5) 0.5286(4) 0.5742(3) 0.0497(11) Uani d . 1
H H14 0.7438 0.4704 0.6278 0.060 Uiso calc R 1
C C15 0.7250(11) 0.5901(4) 0.3915(4) 0.109(3) Uani d . 1
H H15A 0.6469 0.6535 0.4141 0.164 Uiso calc R 1
H H15B 0.6748 0.5641 0.3350 0.164 Uiso calc R 1
H H15C 0.8393 0.6104 0.3680 0.164 Uiso calc R 1
C C16 0.7802(8) 0.3905(4) 0.4514(4) 0.0720(15) Uani d . 1
H H16A 0.7721 0.3403 0.5143 0.108 Uiso calc R 1
H H16B 0.8976 0.3759 0.4177 0.108 Uiso calc R 1
H H16C 0.6935 0.3805 0.4047 0.108 Uiso calc R 1
N N1 0.4629(5) 0.9964(3) 0.6388(3) 0.0507(9) Uani d . 1
N N2 0.5233(4) 0.8215(3) 0.7014(2) 0.0416(8) Uani d . 1
N N3 0.9150(5) 0.8411(3) 0.6746(3) 0.0547(9) Uani d . 1
N N4 0.8164(4) 0.5454(2) 0.8285(2) 0.0355(7) Uani d . 1
N N5 0.8711(4) 0.3896(3) 0.9328(2) 0.0382(7) Uani d . 1
N N6 0.4281(4) 0.5195(3) 0.8494(3) 0.0487(8) Uani d . 1
N N7 0.6785(4) 0.8821(3) 1.0277(2) 0.0429(8) Uani d . 1
N N8 0.7459(5) 0.5038(3) 0.4778(2) 0.0471(8) Uani d . 1
O O1 0.8785(3) 0.7471(2) 0.7320(2) 0.0478(7) Uani d . 1
O O2 0.4629(3) 0.6147(2) 0.7914(2) 0.0508(7) Uani d . 1
O O3 0.6303(4) 0.7528(2) 0.9275(2) 0.0523(7) Uani d . 1
O O4 0.7056(4) 0.6244(2) 0.5996(2) 0.0528(7) Uani d . 1
Cl Cl1 0.90018(14) 0.19042(8) 0.72382(8) 0.0490(3) Uani d . 1
O O5 1.0504(6) 0.2250(4) 0.7606(4) 0.1166(16) Uani d . 1
O O6 0.7487(5) 0.2738(3) 0.7265(3) 0.0903(12) Uani d . 1
O O7 0.9418(5) 0.1610(3) 0.6206(2) 0.0731(10) Uani d . 1
O O8 0.8620(5) 0.0947(3) 0.7917(3) 0.0839(11) 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
O1 Mn1 O2 176.56(11) y
O1 Mn1 N4 89.45(12) y
O2 Mn1 N4 89.88(12) y
O1 Mn1 N2 90.13(13) y
O2 Mn1 N2 90.18(13) y
N4 Mn1 N2 173.75(11) y
O1 Mn1 O4 91.23(11) y
O2 Mn1 O4 92.20(12) y
N4 Mn1 O4 95.89(11) y
N2 Mn1 O4 90.35(11) y
O1 Mn1 O3 87.46(11) y
O2 Mn1 O3 89.13(11) y
N4 Mn1 O3 87.21(10) y
N2 Mn1 O3 86.54(10) y
O4 Mn1 O3 176.62(10) y
C2 C1 N2 108.6(4) ?
C2 C1 H1 125.7 ?
N2 C1 H1 125.7 ?
C1 C2 N1 107.5(4) ?
C1 C2 H2 126.3 ?
N1 C2 H2 126.3 ?
N2 C3 N1 108.9(4) ?
N2 C3 C5 125.5(4) ?
N1 C3 C5 125.5(4) ?
N1 C4 H4A 109.5 ?
N1 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
N1 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
N3 C5 C3 127.9(4) ?
N3 C5 H5 116.1 ?
C3 C5 H5 116.1 ?
C7 C6 N4 108.3(3) ?
C7 C6 H6 125.9 ?
N4 C6 H6 125.9 ?
C6 C7 N5 107.7(3) ?
C6 C7 H7 126.2 ?
N5 C7 H7 126.2 ?
N4 C8 N5 109.7(3) ?
N4 C8 C10 126.5(3) ?
N5 C8 C10 123.7(4) ?
N5 C9 H9A 109.5 ?
N5 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
N5 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
N6 C10 C8 127.3(4) ?
N6 C10 H10 116.3 ?
C8 C10 H10 116.3 ?
O3 C11 N7 124.9(4) ?
O3 C11 H11 117.6 ?
N7 C11 H11 117.6 ?
N7 C12 H12A 109.5 ?
N7 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
N7 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
N7 C13 H13A 109.5 ?
N7 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
N7 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
O4 C14 N8 124.9(4) ?
O4 C14 H14 117.6 ?
N8 C14 H14 117.6 ?
N8 C15 H15A 109.5 ?
N8 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
N8 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N8 C16 H16A 109.5 ?
N8 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
N8 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C3 N1 C2 107.8(4) ?
C3 N1 C4 126.4(4) ?
C2 N1 C4 125.7(4) ?
C3 N2 C1 107.2(4) ?
C3 N2 Mn1 122.2(3) ?
C1 N2 Mn1 130.4(3) ?
C5 N3 O1 118.6(3) ?
C8 N4 C6 107.2(3) ?
C8 N4 Mn1 122.6(2) ?
C6 N4 Mn1 129.8(3) ?
C8 N5 C7 107.1(3) ?
C8 N5 C9 127.0(3) ?
C7 N5 C9 125.9(3) ?
C10 N6 O2 119.1(3) ?
C11 N7 C13 122.0(4) ?
C11 N7 C12 122.2(3) ?
C13 N7 C12 115.8(3) ?
C14 N8 C15 120.2(4) ?
C14 N8 C16 123.1(4) ?
C15 N8 C16 116.7(3) ?
N3 O1 Mn1 133.5(2) ?
N6 O2 Mn1 134.0(2) ?
C11 O3 Mn1 120.4(2) ?
C14 O4 Mn1 129.3(3) ?
O6 Cl1 O7 110.6(2) ?
O6 Cl1 O5 111.4(3) ?
O7 Cl1 O5 109.5(2) ?
O6 Cl1 O8 108.6(2) ?
O7 Cl1 O8 108.9(2) ?
O5 Cl1 O8 107.7(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 O1 1.886(3) y
Mn1 O2 1.893(3) y
Mn1 N4 1.997(3) y
Mn1 N2 2.002(3) y
Mn1 O4 2.204(3) y
Mn1 O3 2.443(3) y
C1 C2 1.344(6) ?
C1 N2 1.372(5) ?
C1 H1 0.9300 ?
C2 N1 1.367(6) ?
C2 H2 0.9300 ?
C3 N2 1.343(5) ?
C3 N1 1.352(5) ?
C3 C5 1.443(6) ?
C4 N1 1.493(5) ?
C4 H4A 0.9600 ?
C4 H4B 0.9600 ?
C4 H4C 0.9600 ?
C5 N3 1.289(5) ?
C5 H5 0.9300 ?
C6 C7 1.351(5) ?
C6 N4 1.377(5) ?
C6 H6 0.9300 ?
C7 N5 1.375(5) ?
C7 H7 0.9300 ?
C8 N4 1.335(5) ?
C8 N5 1.356(4) ?
C8 C10 1.436(5) ?
C9 N5 1.458(5) ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 N6 1.292(5) ?
C10 H10 0.9300 ?
C11 O3 1.249(5) ?
C11 N7 1.304(5) ?
C11 H11 0.9300 ?
C12 N7 1.461(5) ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C13 N7 1.455(5) ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 O4 1.244(5) ?
C14 N8 1.306(5) ?
C14 H14 0.9300 ?
C15 N8 1.437(6) ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 N8 1.455(5) ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
N3 O1 1.350(4) ?
N6 O2 1.362(4) ?
Cl1 O6 1.413(3) ?
Cl1 O7 1.416(3) ?
Cl1 O5 1.420(4) ?
Cl1 O8 1.433(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
_geom_hbond_publ_flag
C2 H2 O7 1_465 0.93 2.54 3.433(6) 161 yes
C5 H5 O7 1_565 0.93 2.60 3.402(6) 145 yes
C12 H12A O8 1_565 0.96 2.49 3.399(6) 157 yes
C13 H13A O3 . 0.96 2.41 2.797(5) 103 yes
C13 H13C O5 2_767 0.96 2.40 3.261(7) 150 yes
C14 H14 O6 . 0.93 2.59 3.477(6) 161 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N2 C1 C2 N1 -0.6(4)
N2 C3 C5 N3 -9.7(7)
N1 C3 C5 N3 173.1(4)
N4 C6 C7 N5 -0.2(4)
N4 C8 C10 N6 -2.3(6)
N5 C8 C10 N6 179.7(4)
N2 C3 N1 C2 -0.3(4)
C5 C3 N1 C2 177.2(4)
N2 C3 N1 C4 178.6(3)
C5 C3 N1 C4 -3.8(6)
C1 C2 N1 C3 0.6(4)
C1 C2 N1 C4 -178.4(3)
N1 C3 N2 C1 0.0(4)
C5 C3 N2 C1 -177.6(3)
N1 C3 N2 Mn1 -175.1(2)
C5 C3 N2 Mn1 7.4(5)
C2 C1 N2 C3 0.4(4)
C2 C1 N2 Mn1 174.9(3)
O1 Mn1 N2 C3 2.4(3)
O2 Mn1 N2 C3 178.9(3)
O4 Mn1 N2 C3 -88.9(3)
O3 Mn1 N2 C3 89.8(3)
O1 Mn1 N2 C1 -171.4(3)
O2 Mn1 N2 C1 5.1(3)
O4 Mn1 N2 C1 97.3(3)
O3 Mn1 N2 C1 -84.0(3)
C3 C5 N3 O1 -2.1(6)
N5 C8 N4 C6 0.5(4)
C10 C8 N4 C6 -177.8(3)
N5 C8 N4 Mn1 -173.4(2)
C10 C8 N4 Mn1 8.3(5)
C7 C6 N4 C8 -0.2(4)
C7 C6 N4 Mn1 173.1(2)
O1 Mn1 N4 C8 168.6(3)
O2 Mn1 N4 C8 -8.1(3)
O4 Mn1 N4 C8 -100.3(3)
O3 Mn1 N4 C8 81.1(3)
O1 Mn1 N4 C6 -3.9(3)
O2 Mn1 N4 C6 179.5(3)
O4 Mn1 N4 C6 87.3(3)
O3 Mn1 N4 C6 -91.4(3)
N4 C8 N5 C7 -0.6(4)
C10 C8 N5 C7 177.7(3)
N4 C8 N5 C9 179.7(3)
C10 C8 N5 C9 -1.9(5)
C6 C7 N5 C8 0.5(4)
C6 C7 N5 C9 -179.9(3)
C8 C10 N6 O2 -1.7(6)
O3 C11 N7 C13 -1.3(6)
O3 C11 N7 C12 178.2(4)
O4 C14 N8 C15 -1.6(7)
O4 C14 N8 C16 179.0(4)
C5 N3 O1 Mn1 16.5(5)
N4 Mn1 O1 N3 171.2(3)
N2 Mn1 O1 N3 -15.0(3)
O3 Mn1 O1 N3 -101.5(3)
C10 N6 O2 Mn1 -1.6(5)
N4 Mn1 O2 N6 5.5(3)
N2 Mn1 O2 N6 -168.3(3)
O4 Mn1 O2 N6 101.4(3)
O3 Mn1 O2 N6 -81.7(3)
N7 C11 O3 Mn1 179.5(3)
O1 Mn1 O3 C11 25.0(3)
O2 Mn1 O3 C11 -155.5(3)
N4 Mn1 O3 C11 114.6(3)
N2 Mn1 O3 C11 -65.2(3)
N8 C14 O4 Mn1 177.9(3)
O1 Mn1 O4 C14 117.2(4)
O2 Mn1 O4 C14 -62.5(4)
N4 Mn1 O4 C14 27.6(4)
N2 Mn1 O4 C14 -152.7(4)
