# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_chemical_name_systematic        ?
_chemical_name_common            'C24 H31 Cl2 Mn N5 O'
_chemical_formula_moiety         'C24 H29 Cl Mn N5, Cl, H2 O'
_chemical_formula_sum            'C24 H31 Cl2 Mn N5 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         531.38
_chemical_absolute_configuration rm

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5670(9)
_cell_length_b                   15.0540(15)
_cell_length_c                   9.7671(13)
_cell_angle_alpha                90
_cell_angle_beta                 119.292(2)
_cell_angle_gamma                90
_cell_volume                     1226.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4333
_cell_measurement_theta_min      2.4410
_cell_measurement_theta_max      28.2029
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       shard
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             554

_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.96



_diffrn_ambient_temperature      100.(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            15045
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             5802
_reflns_number_gt                5174
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0545
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_number_reflns         5802
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0202P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(11)

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'

_computing_data_collection       'Bruker Instrument Service v2011.12.3.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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
C C1 0.4844(2) 0.37702(14) 0.9851(2) 0.0170(4) Uani d . 1 . .
H H1C 0.5645 0.4061 0.9637 0.02 Uiso calc R 1 . .
H H1D 0.5406 0.3318 1.0678 0.02 Uiso calc R 1 . .
C C2 0.4102(2) 0.44550(14) 1.0430(2) 0.0146(4) Uani d . 1 . .
C C3 0.2086(3) 0.54743(14) 0.9808(2) 0.0192(5) Uani d . 1 . .
H H3 0.1115 0.574 0.9043 0.023 Uiso calc R 1 . .
C C4 0.2763(3) 0.57663(15) 1.1334(3) 0.0211(5) Uani d . 1 . .
H H4 0.2286 0.6236 1.1611 0.025 Uiso calc R 1 . .
C C5 0.4140(3) 0.53676(15) 1.2447(3) 0.0228(5) Uani d . 1 . .
H H5 0.4619 0.5549 1.3514 0.027 Uiso calc R 1 . .
C C6 0.4824(3) 0.46995(14) 1.2004(2) 0.0199(5) Uani d . 1 . .
H H6 0.5772 0.4411 1.2762 0.024 Uiso calc R 1 . .
C C7 0.2798(2) 0.26130(13) 0.8786(2) 0.0124(4) Uani d . 1 . .
H H7 0.2554 0.2836 0.9611 0.015 Uiso calc R 1 . .
C C8 0.1213(2) 0.23741(12) 0.7327(2) 0.0124(4) Uani d . 1 . .
H H8 0.1491 0.2125 0.6541 0.015 Uiso calc R 1 . .
C C9 0.0346(3) 0.16369(13) 0.7699(3) 0.0172(5) Uani d . 1 . .
H H9A 0.0042 0.186 0.8471 0.021 Uiso calc R 1 . .
H H9B -0.0649 0.1476 0.673 0.021 Uiso calc R 1 . .
C C10 0.1393(3) 0.08091(14) 0.8362(3) 0.0217(5) Uani d . 1 . .
H H10A 0.0823 0.0361 0.8648 0.026 Uiso calc R 1 . .
H H10B 0.1611 0.0547 0.7556 0.026 Uiso calc R 1 . .
C C11 0.2970(3) 0.10578(14) 0.9810(2) 0.0201(5) Uani d . 1 . .
H H11A 0.2755 0.1271 1.0647 0.024 Uiso calc R 1 . .
H H11B 0.3665 0.0526 1.0206 0.024 Uiso calc R 1 . .
C C12 0.3829(2) 0.17810(13) 0.9412(2) 0.0166(4) Uani d . 1 . .
H H12A 0.4092 0.1554 0.8614 0.02 Uiso calc R 1 . .
H H12B 0.4846 0.1934 1.0365 0.02 Uiso calc R 1 . .
C C13 -0.0669(2) 0.35110(13) 0.7391(2) 0.0144(4) Uani d . 1 . .
H H13A 0.0054 0.3508 0.8541 0.017 Uiso calc R 1 . .
H H13B -0.1586 0.3115 0.7152 0.017 Uiso calc R 1 . .
C C14 -0.1268(2) 0.44429(15) 0.6849(2) 0.0136(4) Uani d . 1 . .
C C15 -0.0917(2) 0.57680(14) 0.5858(2) 0.0157(4) Uani d . 1 . .
H H15 -0.0336 0.6111 0.5488 0.019 Uiso calc R 1 . .
C C16 -0.2220(2) 0.61541(14) 0.5894(2) 0.0172(4) Uani d . 1 . .
H H16 -0.253 0.6749 0.5555 0.021 Uiso calc R 1 . .
C C17 -0.3046(2) 0.56469(15) 0.6437(2) 0.0189(4) Uani d . 1 . .
H H17 -0.3934 0.5894 0.6487 0.023 Uiso calc R 1 . .
C C18 -0.2589(2) 0.47800(14) 0.6909(2) 0.0156(4) Uani d . 1 . .
H H18 -0.3165 0.4423 0.7267 0.019 Uiso calc R 1 . .
C C19 -0.0937(2) 0.30167(14) 0.4915(2) 0.0149(4) Uani d . 1 . .
H H19A -0.1872 0.3415 0.4572 0.018 Uiso calc R 1 . .
H H19B -0.1327 0.2397 0.4782 0.018 Uiso calc R 1 . .
C C20 -0.0186(2) 0.31697(13) 0.3892(2) 0.0152(4) Uani d . 1 . .
C C21 -0.0876(3) 0.28034(14) 0.2384(2) 0.0193(5) Uani d . 1 . .
H H21 -0.1801 0.2438 0.2004 0.023 Uiso calc R 1 . .
C C22 -0.0190(3) 0.29812(15) 0.1461(3) 0.0258(5) Uani d . 1 . .
H H22 -0.065 0.2751 0.0425 0.031 Uiso calc R 1 . .
C C23 0.1177(3) 0.34996(16) 0.2061(3) 0.0248(5) Uani d . 1 . .
H H23 0.1684 0.3618 0.1452 0.03 Uiso calc R 1 . .
C C24 0.1792(3) 0.38415(15) 0.3553(2) 0.0205(5) Uani d . 1 . .
H H24 0.2734 0.4195 0.3962 0.025 Uiso calc R 1 . .
Cl Cl1 0.30412(6) 0.56440(3) 0.62492(6) 0.01979(11) Uani d . 1 . .
Cl Cl2 0.53996(6) 0.27125(3) 0.65015(6) 0.02123(12) Uani d . 1 . .
Mn Mn1 0.19023(3) 0.435397(18) 0.67988(3) 0.01140(7) Uani d . 1 . .
N N1 0.3629(2) 0.33328(11) 0.8417(2) 0.0136(4) Uani d . 1 . .
N N2 0.2743(2) 0.48270(11) 0.93492(19) 0.0156(4) Uani d . 1 . .
N N3 0.0201(2) 0.31796(11) 0.65936(18) 0.0119(3) Uani d . 1 . .
N N4 -0.0447(2) 0.49318(11) 0.63236(18) 0.0130(3) Uani d . 1 . .
N N5 0.1110(2) 0.36933(11) 0.44548(19) 0.0153(4) Uani d . 1 . .
O O1 0.5054(2) 0.26045(13) 0.3073(2) 0.0274(4) Uani d . 1 . .
H H1W 0.502(3) 0.2622(18) 0.390(3) 0.031(8) Uiso d . 1 . .
H H2W 0.550(4) 0.218(2) 0.319(4) 0.052(11) Uiso d . 1 . .
H H1 0.406(3) 0.3132(15) 0.791(3) 0.021(6) Uiso d . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0127(10) 0.0144(10) 0.0214(11) 0.0002(8) 0.0064(9) 0.0000(8)
C2 0.0150(9) 0.0098(10) 0.0177(9) -0.0018(9) 0.0070(8) 0.0001(9)
C3 0.0159(11) 0.0199(12) 0.0195(11) 0.0031(9) 0.0069(9) -0.0017(9)
C4 0.0227(12) 0.0203(12) 0.0235(11) -0.0001(9) 0.0138(10) -0.0066(9)
C5 0.0255(13) 0.0250(12) 0.0165(11) -0.0060(10) 0.0091(10) -0.0075(9)
C6 0.0176(11) 0.0190(11) 0.0161(10) -0.0013(9) 0.0027(9) 0.0000(8)
C7 0.0143(10) 0.0109(10) 0.0148(9) -0.0004(8) 0.0093(8) 0.0000(8)
C8 0.0154(11) 0.0100(10) 0.0130(9) -0.0002(8) 0.0080(9) -0.0005(8)
C9 0.0189(12) 0.0140(11) 0.0189(11) -0.0048(9) 0.0093(10) -0.0018(8)
C10 0.0311(13) 0.0123(11) 0.0233(11) -0.0011(9) 0.0145(11) 0.0021(9)
C11 0.0287(13) 0.0112(10) 0.0213(11) 0.0024(9) 0.0128(11) 0.0043(9)
C12 0.0187(11) 0.0121(10) 0.0202(10) 0.0037(9) 0.0105(10) 0.0014(8)
C13 0.0169(11) 0.0134(10) 0.0172(10) 0.0000(8) 0.0116(9) -0.0012(8)
C14 0.0147(9) 0.0144(11) 0.0113(8) -0.0015(9) 0.0060(8) -0.0012(9)
C15 0.0166(11) 0.0151(11) 0.0134(9) 0.0002(8) 0.0057(9) 0.0020(8)
C16 0.0164(11) 0.0140(11) 0.0151(10) 0.0042(8) 0.0029(9) 0.0013(8)
C17 0.0146(10) 0.0221(11) 0.0183(10) 0.0024(9) 0.0067(9) -0.0046(9)
C18 0.0146(10) 0.0178(11) 0.0154(10) 0.0005(8) 0.0081(9) -0.0028(8)
C19 0.0144(10) 0.0146(10) 0.0140(10) -0.0006(8) 0.0055(9) 0.0002(8)
C20 0.0171(11) 0.0118(10) 0.0152(10) 0.0041(8) 0.0067(9) 0.0003(8)
C21 0.0223(12) 0.0164(11) 0.0155(10) 0.0007(9) 0.0065(9) -0.0002(9)
C22 0.0375(14) 0.0256(13) 0.0160(11) 0.0023(11) 0.0144(11) -0.0022(9)
C23 0.0342(14) 0.0278(13) 0.0207(11) 0.0026(11) 0.0200(11) 0.0014(10)
C24 0.0234(12) 0.0211(12) 0.0220(11) -0.0002(9) 0.0150(10) 0.0011(9)
Cl1 0.0191(3) 0.0159(3) 0.0265(3) -0.0030(2) 0.0127(2) 0.0041(2)
Cl2 0.0227(3) 0.0186(3) 0.0287(3) -0.0027(2) 0.0174(2) -0.0032(2)
Mn1 0.01264(14) 0.01036(14) 0.01257(13) -0.00017(14) 0.00724(12) 0.00095(14)
N1 0.0131(9) 0.0130(9) 0.0173(9) 0.0002(7) 0.0095(8) -0.0013(7)
N2 0.0166(9) 0.0143(9) 0.0156(8) 0.0011(7) 0.0076(8) 0.0002(7)
N3 0.0147(9) 0.0114(9) 0.0115(8) 0.0019(7) 0.0079(7) 0.0017(7)
N4 0.0139(9) 0.0133(9) 0.0115(8) -0.0009(7) 0.0059(7) 0.0003(7)
N5 0.0193(10) 0.0157(9) 0.0139(8) 0.0003(7) 0.0104(8) 0.0014(7)
O1 0.0315(10) 0.0251(10) 0.0273(10) 0.0034(8) 0.0158(8) 0.0031(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 N1 . 1.467(3) ?
C1 C2 . 1.510(3) ?
C1 H1C . 0.99 ?
C1 H1D . 0.99 ?
C2 N2 . 1.332(2) ?
C2 C6 . 1.393(3) ?
C3 N2 . 1.349(3) ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.369(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 N1 . 1.489(3) ?
C7 C12 . 1.525(3) ?
C7 C8 . 1.531(3) ?
C7 H7 . 1.0 ?
C8 N3 . 1.497(2) ?
C8 C9 . 1.532(3) ?
C8 H8 . 1.0 ?
C9 C10 . 1.530(3) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C11 . 1.526(3) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.524(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 N3 . 1.477(2) ?
C13 C14 . 1.510(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 N4 . 1.347(2) ?
C14 C18 . 1.390(3) ?
C15 N4 . 1.339(3) ?
C15 C16 . 1.391(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.379(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.382(3) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 N3 . 1.479(2) ?
C19 C20 . 1.507(3) ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?
C20 N5 . 1.339(3) ?
C20 C21 . 1.399(3) ?
C21 C22 . 1.377(3) ?
C21 H21 . 0.95 ?
C22 C23 . 1.383(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.377(3) ?
C23 H23 . 0.95 ?
C24 N5 . 1.347(2) ?
C24 H24 . 0.95 ?
Cl1 Mn1 . 2.4122(6) ?
Mn1 N4 . 2.2371(17) ?
Mn1 N1 . 2.2441(17) ?
Mn1 N5 . 2.2598(17) ?
Mn1 N2 . 2.3236(17) ?
Mn1 N3 . 2.3440(17) ?
N1 H1 . 0.84(2) ?
O1 H1W . 0.82(3) ?
O1 H2W . 0.75(3) ?

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
N1 C1 C2 . . 111.49(16) ?
N1 C1 H1C . . 109.3 ?
C2 C1 H1C . . 109.3 ?
N1 C1 H1D . . 109.3 ?
C2 C1 H1D . . 109.3 ?
H1C C1 H1D . . 108.0 ?
N2 C2 C6 . . 121.88(19) ?
N2 C2 C1 . . 116.48(17) ?
C6 C2 C1 . . 121.63(18) ?
N2 C3 C4 . . 122.8(2) ?
N2 C3 H3 . . 118.6 ?
C4 C3 H3 . . 118.6 ?
C5 C4 C3 . . 118.7(2) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C4 C5 C6 . . 119.3(2) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C5 C6 C2 . . 118.9(2) ?
C5 C6 H6 . . 120.5 ?
C2 C6 H6 . . 120.5 ?
N1 C7 C12 . . 112.20(15) ?
N1 C7 C8 . . 110.41(15) ?
C12 C7 C8 . . 109.39(16) ?
N1 C7 H7 . . 108.2 ?
C12 C7 H7 . . 108.2 ?
C8 C7 H7 . . 108.2 ?
N3 C8 C7 . . 111.67(15) ?
N3 C8 C9 . . 113.72(16) ?
C7 C8 C9 . . 110.74(16) ?
N3 C8 H8 . . 106.8 ?
C7 C8 H8 . . 106.8 ?
C9 C8 H8 . . 106.8 ?
C10 C9 C8 . . 111.86(17) ?
C10 C9 H9A . . 109.2 ?
C8 C9 H9A . . 109.2 ?
C10 C9 H9B . . 109.2 ?
C8 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
C11 C10 C9 . . 109.75(17) ?
C11 C10 H10A . . 109.7 ?
C9 C10 H10A . . 109.7 ?
C11 C10 H10B . . 109.7 ?
C9 C10 H10B . . 109.7 ?
H10A C10 H10B . . 108.2 ?
C12 C11 C10 . . 110.56(17) ?
C12 C11 H11A . . 109.5 ?
C10 C11 H11A . . 109.5 ?
C12 C11 H11B . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
C11 C12 C7 . . 111.43(16) ?
C11 C12 H12A . . 109.3 ?
C7 C12 H12A . . 109.3 ?
C11 C12 H12B . . 109.3 ?
C7 C12 H12B . . 109.3 ?
H12A C12 H12B . . 108.0 ?
N3 C13 C14 . . 110.14(15) ?
N3 C13 H13A . . 109.6 ?
C14 C13 H13A . . 109.6 ?
N3 C13 H13B . . 109.6 ?
C14 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
N4 C14 C18 . . 121.9(2) ?
N4 C14 C13 . . 116.69(17) ?
C18 C14 C13 . . 121.43(18) ?
N4 C15 C16 . . 122.67(19) ?
N4 C15 H15 . . 118.7 ?
C16 C15 H15 . . 118.7 ?
C17 C16 C15 . . 117.91(19) ?
C17 C16 H16 . . 121.0 ?
C15 C16 H16 . . 121.0 ?
C16 C17 C18 . . 120.27(19) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C17 C18 C14 . . 118.5(2) ?
C17 C18 H18 . . 120.8 ?
C14 C18 H18 . . 120.8 ?
N3 C19 C20 . . 112.24(16) ?
N3 C19 H19A . . 109.2 ?
C20 C19 H19A . . 109.2 ?
N3 C19 H19B . . 109.2 ?
C20 C19 H19B . . 109.2 ?
H19A C19 H19B . . 107.9 ?
N5 C20 C21 . . 121.96(19) ?
N5 C20 C19 . . 117.62(17) ?
C21 C20 C19 . . 120.36(19) ?
C22 C21 C20 . . 118.8(2) ?
C22 C21 H21 . . 120.6 ?
C20 C21 H21 . . 120.6 ?
C21 C22 C23 . . 119.2(2) ?
C21 C22 H22 . . 120.4 ?
C23 C22 H22 . . 120.4 ?
C24 C23 C22 . . 119.0(2) ?
C24 C23 H23 . . 120.5 ?
C22 C23 H23 . . 120.5 ?
N5 C24 C23 . . 122.5(2) ?
N5 C24 H24 . . 118.8 ?
C23 C24 H24 . . 118.8 ?
N4 Mn1 N1 . . 137.00(6) ?
N4 Mn1 N5 . . 98.98(6) ?
N1 Mn1 N5 . . 100.28(6) ?
N4 Mn1 N2 . . 83.61(6) ?
N1 Mn1 N2 . . 72.87(6) ?
N5 Mn1 N2 . . 171.72(6) ?
N4 Mn1 N3 . . 71.97(6) ?
N1 Mn1 N3 . . 77.57(6) ?
N5 Mn1 N3 . . 72.95(6) ?
N2 Mn1 N3 . . 100.63(6) ?
N4 Mn1 Cl1 . . 99.10(4) ?
N1 Mn1 Cl1 . . 116.82(5) ?
N5 Mn1 Cl1 . . 95.33(5) ?
N2 Mn1 Cl1 . . 91.99(5) ?
N3 Mn1 Cl1 . . 163.42(4) ?
C1 N1 C7 . . 111.28(16) ?
C1 N1 Mn1 . . 109.34(12) ?
C7 N1 Mn1 . . 111.88(12) ?
C1 N1 H1 . . 109.4(16) ?
C7 N1 H1 . . 110.9(16) ?
Mn1 N1 H1 . . 103.8(16) ?
C2 N2 C3 . . 118.24(18) ?
C2 N2 Mn1 . . 114.33(13) ?
C3 N2 Mn1 . . 127.17(14) ?
C13 N3 C19 . . 109.94(16) ?
C13 N3 C8 . . 114.84(15) ?
C19 N3 C8 . . 110.45(15) ?
C13 N3 Mn1 . . 104.29(11) ?
C19 N3 Mn1 . . 108.89(11) ?
C8 N3 Mn1 . . 108.11(11) ?
C15 N4 C14 . . 118.82(18) ?
C15 N4 Mn1 . . 124.88(14) ?
C14 N4 Mn1 . . 114.96(13) ?
C20 N5 C24 . . 118.45(18) ?
C20 N5 Mn1 . . 117.33(13) ?
C24 N5 Mn1 . . 124.06(14) ?
H1W O1 H2W . . 100.(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 N2 . . . . -27.2(2) ?
N1 C1 C2 C6 . . . . 154.33(19) ?
N2 C3 C4 C5 . . . . -1.8(3) ?
C3 C4 C5 C6 . . . . 1.3(3) ?
C4 C5 C6 C2 . . . . 0.7(3) ?
N2 C2 C6 C5 . . . . -2.3(3) ?
C1 C2 C6 C5 . . . . 176.11(19) ?
N1 C7 C8 N3 . . . . -51.9(2) ?
C12 C7 C8 N3 . . . . -175.84(15) ?
N1 C7 C8 C9 . . . . -179.72(16) ?
C12 C7 C8 C9 . . . . 56.3(2) ?
N3 C8 C9 C10 . . . . 176.84(17) ?
C7 C8 C9 C10 . . . . -56.5(2) ?
C8 C9 C10 C11 . . . . 56.0(2) ?
C9 C10 C11 C12 . . . . -56.6(2) ?
C10 C11 C12 C7 . . . . 58.9(2) ?
N1 C7 C12 C11 . . . . 179.02(16) ?
C8 C7 C12 C11 . . . . -58.1(2) ?
N3 C13 C14 N4 . . . . -26.0(2) ?
N3 C13 C14 C18 . . . . 154.80(17) ?
N4 C15 C16 C17 . . . . 0.1(3) ?
C15 C16 C17 C18 . . . . -0.7(3) ?
C16 C17 C18 C14 . . . . 1.2(3) ?
N4 C14 C18 C17 . . . . -1.0(3) ?
C13 C14 C18 C17 . . . . 178.16(18) ?
N3 C19 C20 N5 . . . . -22.1(3) ?
N3 C19 C20 C21 . . . . 160.59(18) ?
N5 C20 C21 C22 . . . . 0.6(3) ?
C19 C20 C21 C22 . . . . 177.8(2) ?
C20 C21 C22 C23 . . . . 1.4(3) ?
C21 C22 C23 C24 . . . . -1.6(3) ?
C22 C23 C24 N5 . . . . -0.2(4) ?
C2 C1 N1 C7 . . . . -81.3(2) ?
C2 C1 N1 Mn1 . . . . 42.80(19) ?
C12 C7 N1 C1 . . . . -76.2(2) ?
C8 C7 N1 C1 . . . . 161.50(16) ?
C12 C7 N1 Mn1 . . . . 161.16(13) ?
C8 C7 N1 Mn1 . . . . 38.86(18) ?
N4 Mn1 N1 C1 . . . . -92.44(15) ?
N5 Mn1 N1 C1 . . . . 152.27(13) ?
N2 Mn1 N1 C1 . . . . -32.52(13) ?
N3 Mn1 N1 C1 . . . . -137.92(14) ?
Cl1 Mn1 N1 C1 . . . . 50.88(14) ?
N4 Mn1 N1 C7 . . . . 31.30(17) ?
N5 Mn1 N1 C7 . . . . -83.99(13) ?
N2 Mn1 N1 C7 . . . . 91.22(13) ?
N3 Mn1 N1 C7 . . . . -14.18(12) ?
Cl1 Mn1 N1 C7 . . . . 174.62(10) ?
C6 C2 N2 C3 . . . . 1.8(3) ?
C1 C2 N2 C3 . . . . -176.68(18) ?
C6 C2 N2 Mn1 . . . . 176.32(16) ?
C1 C2 N2 Mn1 . . . . -2.1(2) ?
C4 C3 N2 C2 . . . . 0.3(3) ?
C4 C3 N2 Mn1 . . . . -173.46(16) ?
N4 Mn1 N2 C2 . . . . 162.97(14) ?
N1 Mn1 N2 C2 . . . . 19.40(13) ?
N5 Mn1 N2 C2 . . . . 54.2(5) ?
N3 Mn1 N2 C2 . . . . 92.72(14) ?
Cl1 Mn1 N2 C2 . . . . -98.09(14) ?
N4 Mn1 N2 C3 . . . . -23.08(17) ?
N1 Mn1 N2 C3 . . . . -166.64(18) ?
N5 Mn1 N2 C3 . . . . -131.8(4) ?
N3 Mn1 N2 C3 . . . . -93.33(17) ?
Cl1 Mn1 N2 C3 . . . . 75.87(17) ?
C14 C13 N3 C19 . . . . -70.2(2) ?
C14 C13 N3 C8 . . . . 164.54(16) ?
C14 C13 N3 Mn1 . . . . 46.43(17) ?
C20 C19 N3 C13 . . . . 148.68(16) ?
C20 C19 N3 C8 . . . . -83.6(2) ?
C20 C19 N3 Mn1 . . . . 34.99(19) ?
C7 C8 N3 C13 . . . . -78.5(2) ?
C9 C8 N3 C13 . . . . 47.7(2) ?
C7 C8 N3 C19 . . . . 156.47(15) ?
C9 C8 N3 C19 . . . . -77.32(19) ?
C7 C8 N3 Mn1 . . . . 37.43(17) ?
C9 C8 N3 Mn1 . . . . 163.63(13) ?
N4 Mn1 N3 C13 . . . . -39.23(12) ?
N1 Mn1 N3 C13 . . . . 110.01(12) ?
N5 Mn1 N3 C13 . . . . -144.99(13) ?
N2 Mn1 N3 C13 . . . . 40.39(12) ?
Cl1 Mn1 N3 C13 . . . . -98.57(17) ?
N4 Mn1 N3 C19 . . . . 78.10(12) ?
N1 Mn1 N3 C19 . . . . -132.66(13) ?
N5 Mn1 N3 C19 . . . . -27.66(12) ?
N2 Mn1 N3 C19 . . . . 157.72(12) ?
Cl1 Mn1 N3 C19 . . . . 18.8(2) ?
N4 Mn1 N3 C8 . . . . -161.87(12) ?
N1 Mn1 N3 C8 . . . . -12.63(11) ?
N5 Mn1 N3 C8 . . . . 92.37(12) ?
N2 Mn1 N3 C8 . . . . -82.25(12) ?
Cl1 Mn1 N3 C8 . . . . 138.79(13) ?
C16 C15 N4 C14 . . . . 0.0(3) ?
C16 C15 N4 Mn1 . . . . -166.08(15) ?
C18 C14 N4 C15 . . . . 0.5(3) ?
C13 C14 N4 C15 . . . . -178.78(17) ?
C18 C14 N4 Mn1 . . . . 167.90(14) ?
C13 C14 N4 Mn1 . . . . -11.3(2) ?
N1 Mn1 N4 C15 . . . . 147.89(14) ?
N5 Mn1 N4 C15 . . . . -96.36(16) ?
N2 Mn1 N4 C15 . . . . 91.57(16) ?
N3 Mn1 N4 C15 . . . . -165.03(16) ?
Cl1 Mn1 N4 C15 . . . . 0.57(16) ?
N1 Mn1 N4 C14 . . . . -18.67(18) ?
N5 Mn1 N4 C14 . . . . 97.08(13) ?
N2 Mn1 N4 C14 . . . . -74.99(13) ?
N3 Mn1 N4 C14 . . . . 28.40(13) ?
Cl1 Mn1 N4 C14 . . . . -165.99(12) ?
C21 C20 N5 C24 . . . . -2.4(3) ?
C19 C20 N5 C24 . . . . -179.65(19) ?
C21 C20 N5 Mn1 . . . . 173.25(15) ?
C19 C20 N5 Mn1 . . . . -4.0(2) ?
C23 C24 N5 C20 . . . . 2.2(3) ?
C23 C24 N5 Mn1 . . . . -173.11(17) ?
N4 Mn1 N5 C20 . . . . -50.14(15) ?
N1 Mn1 N5 C20 . . . . 91.23(15) ?
N2 Mn1 N5 C20 . . . . 57.5(5) ?
N3 Mn1 N5 C20 . . . . 17.76(14) ?
Cl1 Mn1 N5 C20 . . . . -150.26(14) ?
N4 Mn1 N5 C24 . . . . 125.21(17) ?
N1 Mn1 N5 C24 . . . . -93.42(17) ?
N2 Mn1 N5 C24 . . . . -127.1(4) ?
N3 Mn1 N5 C24 . . . . -166.89(18) ?
Cl1 Mn1 N5 C24 . . . . 25.09(17) ?

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
O1 H1W Cl2 . 0.82(3) 2.39(3) 3.204(2) 170.(2) ?
O1 H2W Cl1 2_646 0.75(3) 2.62(3) 3.360(2) 175.(3) ?
N1 H1 Cl2 . 0.84(2) 2.38(2) 3.2158(19) 174.(2) ?

_database_code_depnum_ccdc_archive 'CCDC 967858'