#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/72/2227204.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_2227204
loop_
_publ_author_name
'Pojarová, Michaela'
'Fejfarová, Karla'
'El Bali, Brahim'
_publ_section_title
;
 1,4,8,11-Tetraazoniacyclotetradecane diaquatetrachloridomanganese(II)
 dichloride dihydrate
;
_journal_coeditor_code           BT5316
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1103
_journal_paper_doi               10.1107/S1600536810031958
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '(C10 H28 N4) [Mn Cl4 (H2 O)2] Cl2, 2H2 O'
_chemical_formula_moiety
'C10 H28 N4 4+, Cl4 H4 Mn O2 2-, 2(Cl -), 2(H2 O)'
_chemical_formula_sum            'C10 H36 Cl6 Mn N4 O4'
_chemical_formula_weight         544.1
_chemical_name_systematic
;
1,4,8,11-Tetraazoniacyclotetradecane diaquatetrachloridomanganese(II)
dichloride dihydrate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8492(2)
_cell_length_b                   19.3511(3)
_cell_length_c                   7.87720(10)
_cell_measurement_reflns_used    16479
_cell_measurement_temperature    292
_cell_measurement_theta_max      26.4995
_cell_measurement_theta_min      2.5081
_cell_volume                     2263.50(5)
_computing_cell_refinement       'Crysalis RED (Oxford Diffraction, 2005)'
_computing_data_collection       'Crysalis CCD (Oxford Diffraction, 2005)'
_computing_data_reduction        'Crysalis RED(Oxford Diffraction, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
'JANA2006 (Petříček et al., 2006) and publCIF (Westrip, 2010)'
_computing_structure_refinement
'JANA2006 (Petříček et al., 2006)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      292
_diffrn_detector_area_resol_mean 8.3438
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Oxford Diffraction CCD'
_diffrn_measurement_method       'Rotation method data acquisition using ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0109
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26200
_diffrn_reflns_reduction_process
;
Integration of the CCD images was done by program Crysalis RED
(Oxford Diffraction, 2005).
;
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    1.314
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2005)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.59606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.3598
_exptl_crystal_size_mid          0.2190
_exptl_crystal_size_min          0.1588
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.10
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2429
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0179
_refine_ls_shift/su_max          0.0096
_refine_ls_shift/su_mean         0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/[σ²(I)+0.0016I²]
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0589
_reflns_number_gt                1999
_reflns_number_total             2429
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            bt5316.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C10 H36 Cl6 Mn1 N4 O4'
_cod_database_code               2227204
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x+1/2,-y,z+1/2
3 -x,y+1/2,-z
4 x+1/2,-y+1/2,-z+1/2
5 -x,-y,-z
6 x+1/2,y,-z+1/2
7 x,-y+1/2,z
8 -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 0 0 0.01920(9) Uani d . 1 . .
Cl Cl1 -0.06104(2) 0.040619(17) 0.28548(4) 0.02344(10) Uani d . 1 . .
Cl Cl3 0.03588(3) 0.25 0.10590(6) 0.02742(14) Uani d . 1 . .
Cl Cl2 0.14001(2) -0.046308(19) 0.14869(4) 0.03195(11) Uani d . 1 . .
Cl Cl4 0.27203(4) 0.25 0.80690(7) 0.03300(16) Uani d . 1 . .
O O1 0.06526(7) 0.10208(5) -0.04773(13) 0.0246(3) Uani d . 1 . .
O O2 0.24961(7) 0.11049(6) -0.02640(14) 0.0323(3) Uani d . 1 . .
N N1 0.25833(7) 0.12044(5) 0.33251(14) 0.0211(3) Uani d . 1 . .
N N2 0.04152(7) 0.12050(5) 0.59062(14) 0.0203(3) Uani d . 1 . .
C C1 0.15939(9) 0.11683(7) 0.36796(16) 0.0212(4) Uani d . 1 . .
C C2 0.14089(8) 0.11699(7) 0.55731(17) 0.0206(4) Uani d . 1 . .
C C3 -0.00618(8) 0.18592(7) 0.54150(17) 0.0217(4) Uani d . 1 . .
C C4 0.03729(16) 0.25 0.6165(3) 0.0314(6) Uani d . 1 . .
C C5 0.30646(9) 0.18591(6) 0.38037(17) 0.0228(4) Uani d . 1 . .
C C6 0.26338(16) 0.25 0.3046(3) 0.0329(7) Uani d . 1 . .
H H1m 0.268045 0.111373 0.225895 0.0253 Uiso d . 1 . .
H H1n 0.285152 0.085355 0.379572 0.0253 Uiso d . 1 . .
H H2m 0.031159 0.111526 0.697062 0.0244 Uiso d . 1 . .
H H2n 0.015046 0.085424 0.542836 0.0244 Uiso d . 1 . .
H H1a 0.134992 0.075561 0.318388 0.0254 Uiso d . 1 . .
H H1b 0.129816 0.155584 0.31619 0.0254 Uiso d . 1 . .
H H2a 0.165029 0.07569 0.607205 0.0247 Uiso d . 1 . .
H H2b 0.169981 0.156082 0.608522 0.0247 Uiso d . 1 . .
H H3a -0.067928 0.183451 0.577083 0.026 Uiso d . 1 . .
H H3n -0.007609 0.18981 0.420039 0.026 Uiso d . 1 . .
H H4a 0.100476 0.25 0.590704 0.0377 Uiso d . 1 . .
H H4b 0.029252 0.25 0.737419 0.0377 Uiso d . 1 . .
H H5a 0.368181 0.18312 0.344749 0.0273 Uiso d . 1 . .
H H5b 0.308095 0.190111 0.50176 0.0273 Uiso d . 1 . .
H H6a 0.200057 0.25 0.329167 0.0394 Uiso d . 1 . .
H H6b 0.272047 0.25 0.183783 0.0394 Uiso d . 1 . .
H H2o 0.2545(12) 0.1474(6) -0.080(2) 0.0387 Uiso d . 1 . .
H H2p 0.2810(10) 0.0859(8) -0.085(2) 0.0387 Uiso d . 1 . .
H H1o 0.1201(6) 0.1002(8) -0.042(2) 0.0296 Uiso d . 1 . .
H H1p 0.0475(11) 0.1365(6) 0.0039(18) 0.0296 Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.003 0.002 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
H 0.000 0.000 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
N 0.006 0.003 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
Mn 0.337 0.728 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
Cl 0.148 0.159 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
O 0.011 0.006 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 Mn1 Cl1 . . 5_555 180 no
Cl1 Mn1 Cl2 . . . 89.601(11) no
Cl1 Mn1 Cl2 . . 5_555 90.399(11) no
Cl1 Mn1 O1 . . . 91.72(3) no
Cl1 Mn1 O1 . . 5_555 88.28(3) no
Cl1 Mn1 Cl2 5_555 . . 90.399(11) no
Cl1 Mn1 Cl2 5_555 . 5_555 89.601(11) no
Cl1 Mn1 O1 5_555 . . 88.28(3) no
Cl1 Mn1 O1 5_555 . 5_555 91.72(3) no
Cl2 Mn1 Cl2 . . 5_555 180 no
Cl2 Mn1 O1 . . . 91.97(3) no
Cl2 Mn1 O1 . . 5_555 88.03(3) no
Cl2 Mn1 O1 5_555 . . 88.03(3) no
Cl2 Mn1 O1 5_555 . 5_555 91.97(3) no
O1 Mn1 O1 . . 5_555 180 no
H1o O1 H1p . . . 109.3(16) no
H2o O2 H2p . . . 99.4(15) no
C1 N1 C5 . . . 117.34(10) no
C1 N1 H1m . . . 109.47 no
C1 N1 H1n . . . 109.47 no
C5 N1 H1m . . . 109.47 no
C5 N1 H1n . . . 109.47 no
H1m N1 H1n . . . 100.26 no
C2 N2 C3 . . . 117.20(10) no
C2 N2 H2m . . . 109.47 no
C2 N2 H2n . . . 109.47 no
C3 N2 H2m . . . 109.47 no
C3 N2 H2n . . . 109.47 no
H2m N2 H2n . . . 100.45 no
N1 C1 C2 . . . 111.17(10) no
N1 C1 H1a . . . 109.47 no
N1 C1 H1b . . . 109.47 no
C2 C1 H1a . . . 109.47 no
C2 C1 H1b . . . 109.47 no
H1a C1 H1b . . . 107.72 no
N2 C2 C1 . . . 110.50(10) no
N2 C2 H2a . . . 109.47 no
N2 C2 H2b . . . 109.47 no
C1 C2 H2a . . . 109.47 no
C1 C2 H2b . . . 109.47 no
H2a C2 H2b . . . 108.42 no
N2 C3 C4 . . . 112.83(11) no
N2 C3 H3a . . . 109.47 no
N2 C3 H3n . . . 109.47 no
C4 C3 H3a . . . 109.47 no
C4 C3 H3n . . . 109.47 no
H3a C3 H3n . . . 105.89 no
C3 C4 C3 . . 7_555 109.58(15) no
C3 C4 H4a . . . 109.47 no
C3 C4 H4b . . . 109.47 no
C3 C4 H4a 7_555 . . 109.47 no
C3 C4 H4b 7_555 . . 109.47 no
H4a C4 H4b . . . 109.4 no
N1 C5 C6 . . . 112.94(12) no
N1 C5 H5a . . . 109.47 no
N1 C5 H5b . . . 109.47 no
C6 C5 H5a . . . 109.47 no
C6 C5 H5b . . . 109.47 no
H5a C5 H5b . . . 105.77 no
C5 C6 C5 . . 7_555 109.58(16) no
C5 C6 H6a . . . 109.47 no
C5 C6 H6b . . . 109.47 no
C5 C6 H6a 7_555 . . 109.47 no
C5 C6 H6b 7_555 . . 109.47 no
H6a C6 H6b . . . 109.4 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 Cl1 . . 2.5488(3) no
Mn1 Cl1 . 5_555 2.5488(3) no
Mn1 Cl2 . . 2.5490(4) no
Mn1 Cl2 . 5_555 2.5490(4) no
Mn1 O1 . . 2.2322(10) no
Mn1 O1 . 5_555 2.2322(10) no
O1 H1o . . 0.817(9) no
O1 H1p . . 0.824(13) no
O2 H2o . . 0.833(13) no
O2 H2p . . 0.812(15) no
N1 C1 . . 1.4971(17) no
N1 C5 . . 1.5026(16) no
N1 H1m . . 0.8700 no
N1 H1n . . 0.8700 no
N2 C2 . . 1.5004(16) no
N2 C3 . . 1.5013(17) no
N2 H2m . . 0.8700 no
N2 H2n . . 0.8700 no
C1 C2 . . 1.5166(18) no
C1 H1a . . 0.9600 no
C1 H1b . . 0.9600 no
C2 H2a . . 0.9600 no
C2 H2b . . 0.9600 no
C3 C4 . . 1.5176(18) no
C3 H3a . . 0.9600 no
C3 H3n . . 0.9600 no
C4 H4a . . 0.960 no
C4 H4b . . 0.960 no
C5 C6 . . 1.5179(18) no
C5 H5a . . 0.9600 no
C5 H5b . . 0.9600 no
C6 H6a . . 0.960 no
C6 H6b . . 0.960 no
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
N1 H1M O2 . 0.87 2.01 2.8367(16) 159 yes
N1 H1N Cl2 2 0.87 2.51 3.2465(11) 143 yes
N1 H1N Cl1 6 0.87 2.77 3.2317(11) 115 yes
O1 H1O O2 . 0.816(9) 1.937(9) 2.7474(15) 171.5(15) yes
O1 H1P Cl3 . 0.824(13) 2.345(12) 3.1382(10) 161.8(14) yes
N2 H2M O1 1_556 0.87 2.08 2.8926(15) 155 yes
N2 H2N Cl1 . 0.87 2.48 3.2383(11) 146 yes
O2 H2O Cl4 1_554 0.833(13) 2.192(13) 3.0205(12) 173.4(14) yes
O2 H2P Cl2 2_554 0.810(15) 2.523(16) 3.2832(11) 156.8(14) yes
C1 H1A Cl2 . 0.96 2.71 3.6100(14) 156 yes
C3 H3N Cl3 . 0.96 2.81 3.7016(14) 155 yes
C5 H5B Cl4 . 0.96 2.72 3.6178(14) 156 yes
