# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2011
# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full Chem.Commun.
_journal_coden_cambridge 0182
_journal_year ?
_journal_volume ?
_journal_page_first ?
_publ_contact_author_name 'Jie-Sheng Huang'
_publ_contact_author_email jshuang@hku.hk
loop_
_publ_author_name
'Wai-Shan Chow'
'Yungen Liu'
'Chi-Ming Che'
data_complex_1
_database_code_depnum_ccdc_archive 'CCDC 820000'
#TrackingRef '4921_web_deposit_cif_file_0_Jie-ShengHuang_1301910080.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C26 H28 Cl2 Mn N4, C2 H3 N'
_chemical_formula_sum 'C28 H31 Cl2 Mn N5'
_chemical_formula_weight 563.42
_chemical_absolute_configuration ad
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'
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'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21'
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_Int_Tables_number 4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 11.3578(13)
_cell_length_b 8.7479(10)
_cell_length_c 14.5673(17)
_cell_angle_alpha 90.00
_cell_angle_beta 103.890(2)
_cell_angle_gamma 90.00
_cell_volume 1405.0(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 301(2)
_cell_measurement_reflns_used 9882
_cell_measurement_theta_min 2.33
_cell_measurement_theta_max 27.48
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.05
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.332
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 586
_exptl_absorpt_coefficient_mu 0.685
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.8312
_exptl_absorpt_correction_T_max 0.9665
_exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 301(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SAMRT 1000 CCD'
_diffrn_measurement_method '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 9382
_diffrn_reflns_av_R_equivalents 0.0172
_diffrn_reflns_av_sigmaI/netI 0.0387
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 2.60
_diffrn_reflns_theta_max 27.48
_reflns_number_total 5814
_reflns_number_gt 5216
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART (Bruker AXS Inc, 1998)'
_computing_cell_refinement 'SAINT (Bruker AXS Inc, 2006)'
_computing_data_reduction
'SAINT & CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2006)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-II (Johnson, 1976) & MERCURY (Macrae et al., 2008)'
_computing_publication_material 'SHELXL97 (Sheldrick, 2008)'
_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.
The structure was solved by direct methods (SHELXS97) and expanded using
Fourier techniques. All non-H atoms were refined anisotropically.
All of the C-bound H atoms were observable from difference Fourier map but were
all placed at geometrical positions with C---H = 0.93, 0.96, 0.97 and 0.98\%A
for phenyl, methyl, methylene and methine H-atoms. All H-atoms were refined
using riding model with U~iso~(H) = 1.2U~eq~(Carrier).
One restraint have been used in the refinement to fix the origin in an acentric
space group for refinement.
Highest peak is 0.20 at (0.8220, 0.9253, 0.3272) [1.15\%A from H28A]
Deepest hole is -0.19 at (0.4406, 0.5621, 0.1577) [1.38\%A from Mn1]
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0356P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack (1983). 2393 Friedel pairs'
_refine_ls_abs_structure_Flack 0.031(13)
_refine_ls_number_reflns 5814
_refine_ls_number_parameters 329
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0343
_refine_ls_R_factor_gt 0.0287
_refine_ls_wR_factor_ref 0.0695
_refine_ls_wR_factor_gt 0.0671
_refine_ls_goodness_of_fit_ref 1.015
_refine_ls_restrained_S_all 1.015
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.37366(2) 0.55067(3) 0.224637(18) 0.03582(8) Uani 1 1 d . . .
Cl1 Cl 0.42307(6) 0.82111(6) 0.23766(4) 0.05226(14) Uani 1 1 d . . .
Cl2 Cl 0.57225(5) 0.42868(6) 0.24719(4) 0.04697(13) Uani 1 1 d . . .
N1 N 0.33507(13) 0.5469(2) 0.06564(10) 0.0384(3) Uani 1 1 d . . .
N2 N 0.26699(14) 0.3206(2) 0.17235(11) 0.0367(3) Uani 1 1 d . . .
N3 N 0.16892(17) 0.6067(2) 0.23450(13) 0.0451(4) Uani 1 1 d . . .
N4 N 0.36404(17) 0.5317(2) 0.37716(12) 0.0456(4) Uani 1 1 d . . .
N5 N 0.1504(6) 0.2747(8) 0.4502(3) 0.195(3) Uani 1 1 d . . .
C1 C 0.3640(2) 0.6603(3) 0.01535(15) 0.0449(5) Uani 1 1 d . . .
H1 H 0.3725 0.7576 0.0418 0.054 Uiso 1 1 calc R . .
C2 C 0.3827(2) 0.6418(3) -0.07639(16) 0.0505(6) Uani 1 1 d . . .
H2 H 0.4012 0.7250 -0.1101 0.061 Uiso 1 1 calc R . .
C3 C 0.3729(2) 0.4984(3) -0.11419(16) 0.0516(6) Uani 1 1 d . . .
H3 H 0.3860 0.4831 -0.1741 0.062 Uiso 1 1 calc R . .
C4 C 0.34323(19) 0.3733(3) -0.06321(15) 0.0437(5) Uani 1 1 d . . .
C5 C 0.3376(2) 0.2211(3) -0.09615(17) 0.0547(6) Uani 1 1 d . . .
H5 H 0.3490 0.2004 -0.1560 0.066 Uiso 1 1 calc R . .
C6 C 0.3156(2) 0.1049(3) -0.04079(18) 0.0553(6) Uani 1 1 d . . .
H6 H 0.3147 0.0047 -0.0623 0.066 Uiso 1 1 calc R . .
C7 C 0.2942(2) 0.1348(3) 0.04927(17) 0.0479(5) Uani 1 1 d . . .
H7 H 0.2793 0.0537 0.0862 0.057 Uiso 1 1 calc R . .
C8 C 0.29492(17) 0.2807(2) 0.08296(14) 0.0390(4) Uani 1 1 d . . .
C9 C 0.32294(18) 0.4029(2) 0.02776(14) 0.0384(5) Uani 1 1 d . . .
C10 C 0.3147(2) 0.2067(3) 0.24773(15) 0.0465(5) Uani 1 1 d . . .
H10A H 0.2955 0.2386 0.3055 0.056 Uiso 1 1 calc R . .
H10B H 0.4011 0.1990 0.2573 0.056 Uiso 1 1 calc R . .
H10C H 0.2784 0.1089 0.2292 0.056 Uiso 1 1 calc R . .
C11 C 0.1328(2) 0.3488(3) 0.15663(16) 0.0438(5) Uani 1 1 d . . .
H11 H 0.1064 0.4015 0.0958 0.053 Uiso 1 1 calc R . .
C12 C 0.0601(2) 0.2003(4) 0.1495(2) 0.0674(7) Uani 1 1 d . . .
H12A H 0.0725 0.1416 0.0961 0.081 Uiso 1 1 calc R . .
H12B H 0.0908 0.1402 0.2062 0.081 Uiso 1 1 calc R . .
C13 C -0.0752(2) 0.2262(4) 0.1376(2) 0.0838(10) Uani 1 1 d . . .
H13A H -0.1082 0.2801 0.0789 0.101 Uiso 1 1 calc R . .
H13B H -0.1165 0.1287 0.1351 0.101 Uiso 1 1 calc R . .
C14 C -0.0953(2) 0.3191(5) 0.2200(2) 0.0789(9) Uani 1 1 d . . .
H14A H -0.0641 0.2639 0.2786 0.095 Uiso 1 1 calc R . .
H14B H -0.1814 0.3356 0.2131 0.095 Uiso 1 1 calc R . .
C15 C -0.0310(2) 0.4718(4) 0.2235(2) 0.0662(7) Uani 1 1 d . . .
H15A H -0.0439 0.5300 0.2769 0.079 Uiso 1 1 calc R . .
H15B H -0.0666 0.5287 0.1665 0.079 Uiso 1 1 calc R . .
C16 C 0.10578(18) 0.4555(3) 0.23241(15) 0.0445(5) Uani 1 1 d . . .
H16 H 0.1396 0.4065 0.2935 0.053 Uiso 1 1 calc R . .
C17 C 0.1147(3) 0.7095(4) 0.1544(2) 0.0649(8) Uani 1 1 d . . .
H17A H 0.1140 0.6589 0.0958 0.078 Uiso 1 1 calc R . .
H17B H 0.1618 0.8015 0.1590 0.078 Uiso 1 1 calc R . .
H17C H 0.0331 0.7344 0.1566 0.078 Uiso 1 1 calc R . .
C18 C 0.1825(2) 0.6780(3) 0.32600(18) 0.0547(6) Uani 1 1 d . . .
C19 C 0.1068(3) 0.7884(4) 0.3459(3) 0.0840(10) Uani 1 1 d . . .
H19 H 0.0455 0.8282 0.2976 0.101 Uiso 1 1 calc R . .
C20 C 0.1217(4) 0.8426(5) 0.4400(3) 0.1062(15) Uani 1 1 d . . .
H20 H 0.0701 0.9184 0.4522 0.127 Uiso 1 1 calc R . .
C21 C 0.2077(4) 0.7873(5) 0.5114(3) 0.0964(12) Uani 1 1 d . . .
H21 H 0.2127 0.8214 0.5727 0.116 Uiso 1 1 calc R . .
C22 C 0.2914(3) 0.6773(4) 0.49451(19) 0.0664(8) Uani 1 1 d . . .
C23 C 0.3853(3) 0.6162(4) 0.56473(19) 0.0761(9) Uani 1 1 d . . .
H23 H 0.3924 0.6421 0.6277 0.091 Uiso 1 1 calc R . .
C24 C 0.4659(3) 0.5194(4) 0.54127(18) 0.0737(9) Uani 1 1 d . . .
H24 H 0.5287 0.4784 0.5878 0.088 Uiso 1 1 calc R . .
C25 C 0.4540(3) 0.4813(3) 0.44627(17) 0.0587(6) Uani 1 1 d . . .
H25 H 0.5119 0.4176 0.4308 0.070 Uiso 1 1 calc R . .
C26 C 0.2800(2) 0.6267(3) 0.39936(16) 0.0497(5) Uani 1 1 d . . .
C27 C 0.1994(4) 0.2567(6) 0.5272(4) 0.1134(15) Uani 1 1 d . . .
C28 C 0.2520(5) 0.2374(7) 0.6212(4) 0.156(2) Uani 1 1 d . . .
H28A H 0.2344 0.3243 0.6559 0.187 Uiso 1 1 calc R . .
H28B H 0.3382 0.2275 0.6302 0.187 Uiso 1 1 calc R . .
H28C H 0.2202 0.1467 0.6436 0.187 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Mn1 0.03951(14) 0.03629(14) 0.03226(13) 0.00050(14) 0.00979(10) 0.00196(14)
Cl1 0.0689(4) 0.0379(3) 0.0525(3) -0.0030(2) 0.0193(3) -0.0037(2)
Cl2 0.0420(3) 0.0516(3) 0.0482(3) 0.0033(2) 0.0123(2) 0.0066(2)
N1 0.0386(8) 0.0405(8) 0.0357(7) 0.0041(9) 0.0081(6) 0.0041(9)
N2 0.0350(8) 0.0410(8) 0.0350(8) 0.0015(7) 0.0102(6) 0.0028(7)
N3 0.0447(10) 0.0474(10) 0.0432(9) -0.0009(8) 0.0105(8) 0.0086(8)
N4 0.0580(10) 0.0416(10) 0.0378(8) 0.0001(8) 0.0127(7) -0.0018(9)
N5 0.225(6) 0.246(7) 0.103(3) 0.058(4) 0.018(3) -0.074(5)
C1 0.0438(12) 0.0472(13) 0.0426(11) 0.0049(9) 0.0080(9) 0.0028(9)
C2 0.0465(13) 0.0632(16) 0.0438(12) 0.0139(11) 0.0148(10) 0.0066(11)
C3 0.0476(13) 0.0742(17) 0.0344(11) 0.0043(10) 0.0127(9) 0.0108(10)
C4 0.0353(11) 0.0598(13) 0.0355(10) -0.0019(9) 0.0074(8) 0.0092(9)
C5 0.0500(13) 0.0704(17) 0.0428(12) -0.0145(11) 0.0095(10) 0.0081(12)
C6 0.0579(14) 0.0507(13) 0.0570(14) -0.0186(11) 0.0130(11) 0.0016(10)
C7 0.0464(12) 0.0460(12) 0.0532(13) -0.0042(10) 0.0155(10) -0.0027(10)
C8 0.0339(10) 0.0455(11) 0.0374(10) -0.0032(8) 0.0082(8) 0.0024(8)
C9 0.0325(10) 0.0471(12) 0.0345(10) -0.0019(8) 0.0055(7) 0.0041(8)
C10 0.0507(13) 0.0429(12) 0.0453(11) 0.0039(10) 0.0104(10) 0.0022(10)
C11 0.0355(11) 0.0571(14) 0.0384(11) -0.0049(10) 0.0078(8) 0.0003(9)
C12 0.0501(14) 0.0747(18) 0.0800(18) -0.0219(15) 0.0206(13) -0.0173(13)
C13 0.0447(15) 0.110(3) 0.099(2) -0.035(2) 0.0210(15) -0.0214(16)
C14 0.0425(14) 0.111(3) 0.089(2) -0.017(2) 0.0251(13) -0.0140(15)
C15 0.0397(12) 0.0896(19) 0.0730(17) -0.0152(15) 0.0210(11) 0.0042(12)
C16 0.0344(10) 0.0581(14) 0.0415(11) -0.0022(10) 0.0101(8) 0.0014(10)
C17 0.0554(16) 0.0656(17) 0.0731(17) 0.0154(14) 0.0143(13) 0.0214(13)
C18 0.0551(15) 0.0522(13) 0.0641(15) -0.0126(12) 0.0290(12) -0.0004(11)
C19 0.0668(18) 0.090(2) 0.099(2) -0.0334(19) 0.0262(16) 0.0120(16)
C20 0.083(2) 0.116(3) 0.131(3) -0.074(3) 0.047(2) -0.004(2)
C21 0.098(3) 0.119(3) 0.084(2) -0.056(2) 0.044(2) -0.023(2)
C22 0.0780(19) 0.0760(17) 0.0549(15) -0.0247(14) 0.0351(14) -0.0252(15)
C23 0.103(2) 0.090(2) 0.0383(13) -0.0161(14) 0.0232(15) -0.0362(19)
C24 0.101(2) 0.072(2) 0.0398(12) 0.0070(12) 0.0006(13) -0.0173(16)
C25 0.0776(17) 0.0557(13) 0.0395(12) 0.0056(10) 0.0074(11) -0.0002(13)
C26 0.0578(14) 0.0492(12) 0.0475(12) -0.0105(10) 0.0230(10) -0.0096(10)
C27 0.104(3) 0.133(4) 0.103(3) 0.031(3) 0.024(2) -0.023(3)
C28 0.125(4) 0.191(6) 0.124(4) 0.073(4) -0.026(3) -0.030(4)
_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N1 2.2518(15) . ?
Mn1 N4 2.2567(17) . ?
Mn1 N2 2.3784(18) . ?
Mn1 N3 2.4144(19) . ?
Mn1 Cl1 2.4283(7) . ?
Mn1 Cl2 2.4451(6) . ?
N1 C1 1.320(3) . ?
N1 C9 1.369(3) . ?
N2 C8 1.455(3) . ?
N2 C10 1.485(3) . ?
N2 C11 1.506(3) . ?
N3 C18 1.446(3) . ?
N3 C17 1.485(3) . ?
N3 C16 1.502(3) . ?
N4 C25 1.326(3) . ?
N4 C26 1.362(3) . ?
N5 C27 1.137(6) . ?
C1 C2 1.412(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.408(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.412(3) . ?
C4 C9 1.422(3) . ?
C5 C6 1.357(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.415(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.419(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.530(4) . ?
C11 C16 1.532(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.521(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.512(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.517(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.534(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.370(4) . ?
C18 C26 1.415(4) . ?
C19 C20 1.422(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.335(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.415(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.395(5) . ?
C22 C26 1.431(3) . ?
C23 C24 1.350(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.398(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C27 C28 1.367(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Mn1 N4 165.51(6) . . ?
N1 Mn1 N2 72.54(6) . . ?
N4 Mn1 N2 96.42(7) . . ?
N1 Mn1 N3 96.42(6) . . ?
N4 Mn1 N3 71.42(6) . . ?
N2 Mn1 N3 76.53(6) . . ?
N1 Mn1 Cl1 94.52(6) . . ?
N4 Mn1 Cl1 93.41(5) . . ?
N2 Mn1 Cl1 160.04(4) . . ?
N3 Mn1 Cl1 90.30(5) . . ?
N1 Mn1 Cl2 94.44(4) . . ?
N4 Mn1 Cl2 95.56(5) . . ?
N2 Mn1 Cl2 93.22(4) . . ?
N3 Mn1 Cl2 162.04(5) . . ?
Cl1 Mn1 Cl2 103.08(2) . . ?
C1 N1 C9 118.82(18) . . ?
C1 N1 Mn1 123.15(15) . . ?
C9 N1 Mn1 113.81(14) . . ?
C8 N2 C10 112.44(16) . . ?
C8 N2 C11 109.47(15) . . ?
C10 N2 C11 113.51(17) . . ?
C8 N2 Mn1 106.61(12) . . ?
C10 N2 Mn1 105.27(12) . . ?
C11 N2 Mn1 109.19(13) . . ?
C18 N3 C17 113.3(2) . . ?
C18 N3 C16 110.06(19) . . ?
C17 N3 C16 114.27(19) . . ?
C18 N3 Mn1 104.58(13) . . ?
C17 N3 Mn1 107.46(16) . . ?
C16 N3 Mn1 106.37(11) . . ?
C25 N4 C26 118.6(2) . . ?
C25 N4 Mn1 124.13(17) . . ?
C26 N4 Mn1 113.04(15) . . ?
N1 C1 C2 123.6(2) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 118.1(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 123.4(2) . . ?
C3 C4 C9 117.6(2) . . ?
C5 C4 C9 119.0(2) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 121.2(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 118.88(19) . . ?
C7 C8 N2 124.2(2) . . ?
C9 C8 N2 116.96(18) . . ?
N1 C9 C8 118.66(18) . . ?
N1 C9 C4 121.31(19) . . ?
C8 C9 C4 119.97(19) . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 112.4(2) . . ?
N2 C11 C16 111.17(17) . . ?
C12 C11 C16 111.6(2) . . ?
N2 C11 H11 107.1 . . ?
C12 C11 H11 107.1 . . ?
C16 C11 H11 107.1 . . ?
C13 C12 C11 113.3(3) . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 109.3(2) . . ?
C14 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 C15 109.6(3) . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 C16 113.0(2) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
N3 C16 C11 111.95(18) . . ?
N3 C16 C15 112.9(2) . . ?
C11 C16 C15 111.71(18) . . ?
N3 C16 H16 106.6 . . ?
C11 C16 H16 106.6 . . ?
C15 C16 H16 106.6 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C26 118.8(2) . . ?
C19 C18 N3 124.5(3) . . ?
C26 C18 N3 116.8(2) . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 121.7(3) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 120.5(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 124.1(3) . . ?
C23 C22 C26 117.9(3) . . ?
C21 C22 C26 118.0(3) . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 119.3(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
N4 C25 C24 123.1(3) . . ?
N4 C25 H25 118.5 . . ?
C24 C25 H25 118.5 . . ?
N4 C26 C18 118.7(2) . . ?
N4 C26 C22 120.8(2) . . ?
C18 C26 C22 120.4(2) . . ?
N5 C27 C28 176.6(7) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max 0.201
_refine_diff_density_min -0.190
_refine_diff_density_rms 0.041