(2,5-Di­methyl­imidazole){N,N′,N′′,N′′′-[porphyrin-5,10,15,20-tetra­yltetra­(2,1-phenyl­ene)]tetra­kis(pyridine-3-carboxamide)}manganese(II) chloro­benzene disolvate

In the title compound, [Mn(C₆₈H₄₄N₁₂O₄)(C₅H₈N₂)]·2C₆H₅Cl, the central Mn^II ion is coordinated by four pyrrole N atoms of the porphyrin core in the basal sites and one N atom of the 2,5-di­methyl­imidazole ligand in the apical site. Two chloro­benzene solvent mol­ecules are also present in the asymmetric unit. Due to the apical imidazole ligand, the Mn atom is displaced out of the 24-atom porphyrin mean plane by 0.66 Å. The average Mn—N_p (p = porphyrin) bond length is 2.143 (8) Å, and the axial Mn—N_Im (Im = 2,5-di­methyl­imidazole) bond length is 2.171 (8) Å. The structure displays inter­molecular and intra­molecular N—H...O, N—H...N, C—H...O and C—H...N hydrogen bonding. The crystal studied was refined as a two-component inversion twin.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 101 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.080
• wR factor = 0.240
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.410
           From the CIF: _refine_ls_abs_structure_Flack_su    0.040
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        4.7 Ratio
PLAT220_ALERT_2_C NonSolvent   Resd 1  N   Ueq(max)/Ueq(min) Range        3.8 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        4.2 Ratio
PLAT234_ALERT_4_C Large Hirshfeld Difference Cl1S     --C4S      .       0.22 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C1S      --C3S      .       0.19 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C1S      --C5S      .       0.22 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C2S      --C6S      .       0.22 Ang.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C36 Check
PLAT243_ALERT_4_C High   'Solvent' Ueq as Compared to Neighbors of        C4S Check
PLAT243_ALERT_4_C High   'Solvent' Ueq as Compared to Neighbors of       C12S Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C1S Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C2S Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C7S Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01347 Ang.
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N8       --H8A      .     Please Check
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N10      --H10      .     Please Check
PLAT601_ALERT_2_C Unit Cell Contains Solvent Accessible VOIDS of .         34 Ang   3
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         13 Report
                1  4  0,   2  7  0,   6  0  0,   7  1  0,   8  0  0,   9 11  0,
               10  0  0,   1  1  1,   6  0  1,  10  0  1,   4  0  2,   5  8  5,
                1  8  6,
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          7 Note
                1  4  0,   6  0  0,   7  1  0,   8  0  0,  10  0  0,   6  0  1,
               10  0  1,
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          3 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          5 Report
              H6    H7A   H8A   H9    H10
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.61 mm
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      24.16 Why ?
PLAT231_ALERT_4_G Hirshfeld Test (Solvent)   C2S      --C4S      .        9.3 s.u.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O3       ..C36      .       2.99 Ang.
                                         1/2-x,-1/2+y,1/2+z  =      3_545 Check
PLAT794_ALERT_5_G Tentative Bond Valency for Mn1       (II)      .       2.22 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
                1  1  0,   2  0  0,   0  1  1,   2  0  1,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         65 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          4 Note
                0  1 -1,   1  8 -6,   1  8  6,   5  8 -5,
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       6.51 Note
              Predicted wR2: Based on SigI   2  3.69 or SHELX Weight 23.35       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  21 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  13 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
  14 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

Computing details

(2,5-Dimethylimidazole){N,N',N'',N'''-[porphyrin-5,10,15,20-tetrayltetra(2,1-phenylene)]tetrakis(pyridine-3-carboxamide)}manganese(II) chlorobenzene disolvate

Crystal data

[Mn(C68H44N12O4)(C5H8N2)]·2C6H5Cl	Dx = 1.368 Mg m^−3
Mr = 1469.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 9672 reflections
a = 30.247 (4) Å	θ = 2.5–26.3°
b = 13.713 (2) Å	µ = 0.33 mm^−1
c = 17.205 (2) Å	T = 101 K
V = 7136.2 (16) Å^3	Block, black
Z = 4	0.61 × 0.55 × 0.35 mm
F(000) = 3044

Data collection

Bruker APEXII CCD diffractometer	12171 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.071
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 26.6°, θmin = 2.0°
Tmin = 0.568, Tmax = 0.745	h = −37→37
142482 measured reflections	k = −17→17
14653 independent reflections	l = −21→21

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.080	w = 1/[σ^2(Fo^2) + (0.1079P)^2 + 24.1645P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.240	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.98 e Å^−3
14653 reflections	Δρmin = −1.03 e Å^−3
946 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: 0.41 (4)
Primary atom site location: dual

Special details

Geometry. 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.

Refinement. Refined as a 2-component inversion twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Mn1	0.45525 (4)	0.06614 (8)	0.17877 (7)	0.0281 (3)
N1	0.4348 (2)	−0.0793 (4)	0.2054 (4)	0.0262 (13)
N2	0.4298 (2)	0.1066 (5)	0.2903 (4)	0.0279 (13)
N3	0.4393 (2)	0.2123 (5)	0.1452 (4)	0.0289 (13)
N4	0.4429 (2)	0.0271 (5)	0.0595 (4)	0.0271 (13)
C4	0.4360 (3)	−0.1573 (5)	0.1553 (4)	0.0251 (15)
C1	0.4293 (3)	−0.1147 (5)	0.2795 (4)	0.0270 (15)
C19	0.4243 (2)	0.0426 (5)	0.3515 (4)	0.0255 (14)
C16	0.4268 (3)	0.1998 (6)	0.3193 (5)	0.0300 (16)
C14	0.4347 (3)	0.2913 (5)	0.1942 (4)	0.0299 (16)
C11	0.4395 (3)	0.2489 (6)	0.0699 (5)	0.0287 (15)
C9	0.4409 (3)	0.0900 (6)	−0.0030 (4)	0.0279 (15)
C6	0.4424 (3)	−0.0655 (6)	0.0300 (4)	0.0292 (16)
C3	0.4323 (3)	−0.2477 (5)	0.2004 (4)	0.0295 (16)
H3	0.432566	−0.312405	0.180631	0.035*
C2	0.4283 (3)	−0.2206 (6)	0.2763 (5)	0.0318 (17)
H2	0.425412	−0.263366	0.319432	0.038*
C18	0.4181 (3)	0.0991 (6)	0.4221 (4)	0.0339 (18)
H18	0.413455	0.073443	0.472722	0.041*
C17	0.4200 (3)	0.1945 (6)	0.4031 (4)	0.0321 (17)
H17	0.417493	0.248084	0.437833	0.038*
C13	0.4340 (3)	0.3799 (6)	0.1479 (5)	0.0344 (17)
H13	0.431639	0.444585	0.167184	0.041*
C12	0.4372 (3)	0.3535 (6)	0.0724 (5)	0.0335 (17)
H12	0.437852	0.396232	0.028974	0.040*
C8	0.4404 (3)	0.0337 (6)	−0.0748 (5)	0.0343 (18)
H8	0.439129	0.059094	−0.126106	0.041*
C7	0.4419 (3)	−0.0621 (6)	−0.0543 (5)	0.0337 (17)
H7	0.442578	−0.116402	−0.088618	0.040*
C5	0.4391 (3)	−0.1523 (6)	0.0742 (4)	0.0286 (16)
C20	0.4238 (3)	−0.0582 (6)	0.3470 (4)	0.0279 (15)
C15	0.4287 (3)	0.2852 (6)	0.2751 (4)	0.0287 (16)
C10	0.4390 (3)	0.1915 (5)	0.0011 (5)	0.0285 (15)
C38	0.4317 (3)	0.2450 (6)	−0.0742 (4)	0.0328 (17)
C43	0.3902 (3)	0.2874 (6)	−0.0896 (5)	0.0346 (17)
C42	0.3823 (3)	0.3348 (7)	−0.1599 (5)	0.041 (2)
H42	0.354400	0.363857	−0.170375	0.049*
C41	0.4162 (4)	0.3385 (7)	−0.2143 (5)	0.043 (2)
H41	0.411037	0.370699	−0.262340	0.052*
C40	0.4568 (3)	0.2973 (7)	−0.2011 (5)	0.041 (2)
H40	0.479286	0.299728	−0.239652	0.050*
C39	0.4645 (3)	0.2518 (6)	−0.1300 (5)	0.0370 (18)
H39	0.492859	0.224862	−0.119639	0.044*
C26	0.4362 (3)	−0.2455 (6)	0.0290 (4)	0.0299 (16)
C31	0.3979 (3)	−0.2690 (6)	−0.0133 (5)	0.0333 (17)
C30	0.3956 (3)	−0.3541 (6)	−0.0573 (5)	0.0387 (19)
H30	0.369625	−0.368807	−0.085973	0.046*
C29	0.4311 (3)	−0.4166 (6)	−0.0592 (5)	0.041 (2)
H29	0.429615	−0.474211	−0.089785	0.049*
C28	0.4693 (4)	−0.3962 (6)	−0.0166 (5)	0.043 (2)
H28	0.493690	−0.439754	−0.018096	0.052*
C27	0.4714 (3)	−0.3119 (6)	0.0279 (5)	0.0342 (17)
H27	0.497053	−0.299127	0.058142	0.041*
C62	0.4133 (3)	−0.1143 (5)	0.4194 (4)	0.0289 (16)
C67	0.3725 (3)	−0.1613 (6)	0.4269 (4)	0.0318 (17)
C66	0.3630 (3)	−0.2179 (7)	0.4948 (5)	0.041 (2)
H66	0.335455	−0.250347	0.500374	0.049*
C65	0.3950 (3)	−0.2241 (6)	0.5522 (5)	0.040 (2)
H65	0.389080	−0.261811	0.597376	0.048*
C64	0.4355 (3)	−0.1768 (7)	0.5457 (5)	0.039 (2)
H64	0.457141	−0.182661	0.585507	0.047*
C63	0.4439 (3)	−0.1204 (6)	0.4797 (5)	0.0334 (17)
H63	0.470918	−0.085468	0.475856	0.040*
C50	0.4216 (3)	0.3793 (5)	0.3174 (5)	0.0304 (16)
C55	0.3806 (3)	0.4020 (6)	0.3517 (5)	0.0332 (17)
C54	0.3749 (3)	0.4881 (6)	0.3924 (5)	0.0395 (19)
H54	0.347039	0.502786	0.414984	0.047*
C53	0.4101 (4)	0.5537 (6)	0.4006 (5)	0.043 (2)
H53	0.406239	0.612243	0.429356	0.052*
C52	0.4507 (3)	0.5327 (6)	0.3662 (5)	0.041 (2)
H52	0.474763	0.576813	0.371583	0.049*
C51	0.4560 (3)	0.4474 (6)	0.3244 (5)	0.0343 (18)
H51	0.483525	0.434614	0.299801	0.041*
C21	0.5500 (3)	−0.0324 (7)	0.1896 (7)	0.050 (2)
H21	0.539801	−0.088773	0.163089	0.059*
C22	0.5911 (4)	−0.0208 (8)	0.2188 (6)	0.055 (3)
C23	0.6282 (5)	−0.0939 (14)	0.2290 (11)	0.099 (5)
H23A	0.654723	−0.070274	0.202121	0.148*
H23B	0.619323	−0.156791	0.206977	0.148*
H23C	0.634676	−0.101800	0.284452	0.148*
C24	0.5516 (3)	0.1122 (6)	0.2425 (5)	0.0347 (17)
C25	0.5403 (3)	0.2105 (7)	0.2705 (6)	0.044 (2)
H25A	0.565198	0.236989	0.300271	0.066*
H25B	0.514134	0.206798	0.303958	0.066*
H25C	0.534110	0.253002	0.226096	0.066*
C44	0.3205 (3)	0.3335 (7)	−0.0220 (5)	0.042 (2)
C45	0.2967 (3)	0.3183 (7)	0.0538 (5)	0.0381 (19)
C49	0.3200 (3)	0.2978 (7)	0.1214 (5)	0.042 (2)
H49	0.351180	0.291514	0.118252	0.051*
C46	0.2518 (4)	0.3300 (9)	0.0590 (6)	0.054 (3)
H46	0.235080	0.347755	0.014461	0.064*
C47	0.2312 (4)	0.3157 (12)	0.1291 (7)	0.069 (4)
H47	0.199932	0.321103	0.133299	0.082*
C48	0.2562 (4)	0.2938 (10)	0.1924 (6)	0.060 (3)
H48	0.241461	0.283059	0.240442	0.072*
C32	0.3453 (3)	−0.1570 (7)	−0.0738 (5)	0.040 (2)
C33	0.3165 (4)	−0.0722 (7)	−0.0565 (6)	0.046 (2)
C34	0.3268 (4)	−0.0108 (7)	0.0064 (6)	0.055 (3)
H34	0.351483	−0.025289	0.038401	0.065*
C37	0.2820 (5)	−0.0483 (8)	−0.1046 (7)	0.068 (4)
H37	0.276962	−0.085239	−0.150433	0.081*
C35	0.3018 (5)	0.0688 (8)	0.0218 (7)	0.077 (5)
H35	0.308722	0.110647	0.064047	0.093*
C36	0.2662 (8)	0.0871 (11)	−0.0256 (9)	0.117 (8)
H36	0.248724	0.143239	−0.015163	0.141*
C68	0.3074 (3)	−0.2106 (7)	0.3468 (5)	0.042 (2)
C69	0.2886 (3)	−0.1948 (7)	0.2677 (5)	0.0401 (19)
C73	0.3156 (3)	−0.1769 (6)	0.2041 (5)	0.0387 (19)
H73	0.346403	−0.169205	0.212802	0.046*
C70	0.2435 (4)	−0.2042 (11)	0.2552 (7)	0.066 (3)
H70	0.223972	−0.218568	0.296836	0.079*
C71	0.2279 (4)	−0.1921 (12)	0.1808 (8)	0.078 (4)
H71	0.196986	−0.194992	0.171200	0.094*
C72	0.2571 (4)	−0.1758 (9)	0.1193 (7)	0.059 (3)
H72	0.245625	−0.168762	0.068217	0.071*
C56	0.3202 (3)	0.2986 (7)	0.4006 (5)	0.0395 (19)
C57	0.2937 (3)	0.2114 (6)	0.3789 (5)	0.0370 (18)
C58	0.3101 (4)	0.1405 (7)	0.3272 (6)	0.050 (2)
H58	0.337908	0.149512	0.302639	0.060*
C61	0.2534 (4)	0.1957 (8)	0.4125 (7)	0.058 (3)
H61	0.243320	0.241724	0.449769	0.070*
C59	0.2858 (6)	0.0588 (9)	0.3128 (7)	0.080 (5)
H59	0.296744	0.009203	0.279320	0.096*
C60	0.2464 (6)	0.0501 (10)	0.3467 (8)	0.094 (6)
H60	0.230164	−0.007726	0.336369	0.113*
C1S	0.3496 (2)	0.5649 (7)	0.1213 (5)	0.065 (3)
H1S	0.377136	0.566780	0.094747	0.078*
C5S	0.3103 (3)	0.5676 (7)	0.0795 (5)	0.101 (6)
H5S	0.310965	0.571380	0.024379	0.121*
C4S	0.2700 (2)	0.5649 (7)	0.1184 (7)	0.122 (9)
C2S	0.2691 (3)	0.5594 (8)	0.1990 (7)	0.088 (5)
H2S	0.241542	0.557478	0.225562	0.106*
C6S	0.3084 (3)	0.5566 (8)	0.2408 (5)	0.100 (6)
H6S	0.307712	0.552877	0.295932	0.120*
C3S	0.3486 (3)	0.5594 (7)	0.2020 (5)	0.084 (5)
H3S	0.375509	0.557528	0.230526	0.101*
C7S	0.0972 (4)	0.0367 (8)	0.1522 (6)	0.052 (2)
C8S	0.1144 (4)	0.0883 (8)	0.2146 (6)	0.058 (3)
H8S	0.095431	0.111217	0.254540	0.069*
C9S	0.1574 (5)	0.1054 (10)	0.2181 (8)	0.073 (4)
H9S	0.168861	0.144867	0.258808	0.088*
C10S	0.1236 (4)	−0.0035 (9)	0.0967 (6)	0.057 (3)
H10S	0.111343	−0.041601	0.055922	0.068*
C11S	0.1681 (5)	0.0125 (12)	0.1011 (8)	0.076 (4)
H11S	0.187073	−0.012897	0.062139	0.091*
C12S	0.1858 (5)	0.0665 (14)	0.1633 (9)	0.093 (5)
H12S	0.216837	0.076154	0.167499	0.111*
Cl1S	0.22099 (16)	0.5730 (4)	0.0715 (3)	0.1114 (16)
Cl2S	0.04023 (12)	0.0223 (4)	0.1439 (2)	0.0998 (15)
N5	0.5252 (2)	0.0496 (5)	0.2041 (4)	0.0356 (15)
N6	0.5922 (3)	0.0716 (6)	0.2505 (5)	0.0437 (18)
H6	0.615329	0.099384	0.272268	0.052*
N7	0.3617 (2)	−0.2033 (5)	−0.0110 (4)	0.0355 (15)
H7A	0.349239	−0.192075	0.034294	0.043*
N8	0.3568 (3)	0.2791 (5)	−0.0313 (4)	0.0365 (15)
H8A	0.360605	0.232130	0.002861	0.044*
N9	0.3452 (2)	0.3352 (5)	0.3425 (4)	0.0347 (15)
H9	0.339016	0.315991	0.294934	0.042*
N10	0.3418 (2)	−0.1535 (5)	0.3659 (4)	0.0355 (15)
H10	0.345720	−0.102892	0.335286	0.043*
N11	0.3005 (3)	−0.1697 (6)	0.1306 (5)	0.0476 (19)
N12	0.3006 (3)	0.2865 (7)	0.1911 (4)	0.0485 (19)
N13	0.2545 (6)	0.0296 (9)	−0.0866 (7)	0.101 (5)
N14	0.2268 (4)	0.1181 (9)	0.3960 (8)	0.085 (4)
O1	0.3205 (3)	0.3298 (6)	0.4678 (4)	0.0564 (19)
O2	0.3549 (2)	−0.1787 (5)	−0.1415 (4)	0.0496 (17)
O3	0.2929 (4)	−0.2738 (8)	0.3903 (5)	0.091 (4)
O4	0.3066 (3)	0.3919 (8)	−0.0691 (5)	0.082 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0395 (6)	0.0223 (5)	0.0227 (5)	−0.0016 (4)	0.0000 (5)	0.0008 (5)
N1	0.041 (4)	0.017 (3)	0.021 (3)	−0.003 (2)	−0.002 (2)	−0.002 (2)
N2	0.043 (4)	0.021 (3)	0.020 (3)	−0.003 (3)	0.003 (3)	0.001 (2)
N3	0.044 (4)	0.022 (3)	0.021 (3)	0.001 (3)	−0.003 (3)	0.001 (3)
N4	0.039 (3)	0.022 (3)	0.020 (3)	0.000 (3)	−0.001 (3)	0.001 (2)
C4	0.041 (4)	0.011 (3)	0.023 (3)	0.000 (3)	−0.001 (3)	0.000 (3)
C1	0.035 (4)	0.021 (4)	0.025 (4)	−0.004 (3)	0.001 (3)	0.002 (3)
C19	0.034 (4)	0.022 (3)	0.020 (3)	0.001 (3)	−0.001 (3)	−0.002 (3)
C16	0.045 (4)	0.022 (4)	0.023 (4)	0.004 (3)	0.001 (3)	0.006 (3)
C14	0.042 (4)	0.023 (3)	0.025 (4)	−0.001 (3)	−0.002 (3)	−0.002 (3)
C11	0.039 (4)	0.022 (4)	0.026 (4)	0.000 (3)	−0.001 (3)	0.005 (3)
C9	0.034 (4)	0.028 (4)	0.021 (3)	0.000 (3)	0.001 (3)	0.002 (3)
C6	0.041 (4)	0.028 (4)	0.019 (3)	−0.003 (3)	−0.003 (3)	−0.003 (3)
C3	0.048 (4)	0.016 (3)	0.025 (4)	−0.005 (3)	0.002 (3)	0.004 (3)
C2	0.045 (4)	0.024 (4)	0.026 (4)	−0.002 (3)	0.002 (3)	0.004 (3)
C18	0.057 (5)	0.026 (4)	0.019 (4)	0.000 (3)	0.003 (3)	0.001 (3)
C17	0.055 (5)	0.021 (4)	0.019 (4)	0.003 (3)	−0.002 (3)	−0.005 (3)
C13	0.044 (4)	0.028 (4)	0.031 (4)	−0.005 (3)	−0.004 (3)	0.000 (3)
C12	0.049 (5)	0.018 (4)	0.034 (4)	−0.003 (3)	−0.003 (4)	0.002 (3)
C8	0.050 (5)	0.031 (4)	0.022 (4)	0.003 (4)	0.000 (3)	0.004 (3)
C7	0.048 (5)	0.030 (4)	0.024 (4)	−0.001 (3)	0.001 (3)	−0.004 (3)
C5	0.036 (4)	0.027 (4)	0.023 (4)	−0.004 (3)	−0.001 (3)	0.000 (3)
C20	0.034 (4)	0.031 (4)	0.019 (3)	−0.002 (3)	−0.001 (3)	0.002 (3)
C15	0.039 (4)	0.023 (4)	0.024 (4)	0.004 (3)	−0.003 (3)	0.001 (3)
C10	0.038 (4)	0.024 (4)	0.024 (4)	−0.001 (3)	−0.002 (3)	0.008 (3)
C38	0.053 (5)	0.024 (4)	0.021 (4)	−0.003 (3)	0.000 (3)	0.006 (3)
C43	0.048 (5)	0.027 (4)	0.028 (4)	−0.001 (3)	0.001 (4)	0.003 (3)
C42	0.053 (5)	0.037 (5)	0.032 (4)	0.002 (4)	−0.002 (4)	0.012 (4)
C41	0.068 (6)	0.037 (5)	0.025 (4)	−0.003 (4)	0.000 (4)	0.004 (3)
C40	0.056 (5)	0.036 (4)	0.032 (4)	−0.001 (4)	0.006 (4)	0.006 (4)
C39	0.045 (4)	0.029 (4)	0.038 (4)	0.000 (3)	0.005 (4)	0.004 (3)
C26	0.042 (4)	0.028 (4)	0.020 (3)	−0.002 (3)	0.002 (3)	−0.003 (3)
C31	0.050 (5)	0.025 (4)	0.025 (4)	−0.003 (3)	−0.005 (3)	−0.002 (3)
C30	0.059 (5)	0.030 (4)	0.027 (4)	−0.003 (4)	−0.004 (4)	−0.009 (3)
C29	0.065 (6)	0.027 (4)	0.032 (4)	−0.001 (4)	0.002 (4)	−0.005 (3)
C28	0.070 (6)	0.026 (4)	0.033 (4)	0.005 (4)	0.005 (4)	−0.003 (3)
C27	0.047 (5)	0.026 (4)	0.030 (4)	−0.001 (3)	−0.001 (3)	0.000 (3)
C62	0.044 (4)	0.024 (4)	0.019 (3)	0.002 (3)	0.000 (3)	0.001 (3)
C67	0.042 (4)	0.031 (4)	0.022 (4)	−0.001 (3)	0.003 (3)	0.008 (3)
C66	0.053 (5)	0.037 (4)	0.032 (4)	−0.003 (4)	0.006 (4)	0.011 (4)
C65	0.068 (6)	0.032 (4)	0.021 (4)	−0.001 (4)	0.003 (4)	0.004 (3)
C64	0.061 (6)	0.036 (4)	0.021 (4)	0.008 (4)	0.000 (4)	0.003 (3)
C63	0.042 (4)	0.034 (4)	0.024 (4)	−0.004 (3)	−0.003 (3)	0.001 (3)
C50	0.048 (5)	0.015 (3)	0.028 (4)	0.000 (3)	−0.001 (3)	0.000 (3)
C55	0.046 (4)	0.021 (3)	0.032 (4)	−0.003 (3)	0.001 (3)	0.000 (3)
C54	0.059 (5)	0.022 (4)	0.037 (5)	0.004 (4)	0.010 (4)	−0.003 (3)
C53	0.070 (6)	0.021 (4)	0.038 (5)	−0.005 (4)	0.008 (4)	−0.008 (3)
C52	0.061 (6)	0.025 (4)	0.036 (5)	−0.002 (4)	−0.002 (4)	0.000 (3)
C51	0.050 (5)	0.019 (4)	0.034 (4)	−0.001 (3)	0.001 (3)	0.000 (3)
C21	0.060 (6)	0.039 (4)	0.050 (6)	0.017 (4)	−0.009 (5)	−0.005 (4)
C22	0.065 (7)	0.055 (6)	0.043 (6)	0.018 (5)	−0.007 (5)	−0.015 (5)
C23	0.064 (9)	0.117 (14)	0.115 (13)	0.024 (9)	−0.013 (9)	−0.025 (11)
C24	0.046 (5)	0.033 (4)	0.025 (4)	0.000 (3)	0.001 (3)	0.006 (3)
C25	0.054 (5)	0.033 (4)	0.044 (5)	−0.004 (4)	−0.015 (4)	0.007 (4)
C44	0.048 (5)	0.046 (5)	0.032 (5)	0.006 (4)	−0.003 (4)	0.008 (4)
C45	0.045 (5)	0.039 (5)	0.031 (4)	0.000 (4)	−0.003 (4)	0.003 (4)
C49	0.050 (5)	0.042 (5)	0.034 (4)	−0.004 (4)	0.000 (4)	0.005 (4)
C46	0.053 (6)	0.074 (7)	0.034 (5)	0.004 (5)	−0.002 (4)	−0.005 (5)
C47	0.041 (5)	0.117 (11)	0.048 (6)	−0.003 (6)	0.001 (5)	−0.012 (7)
C48	0.057 (6)	0.087 (8)	0.036 (6)	−0.017 (6)	−0.001 (4)	−0.006 (5)
C32	0.058 (5)	0.033 (4)	0.030 (4)	0.003 (4)	−0.007 (4)	−0.001 (3)
C33	0.067 (6)	0.030 (4)	0.039 (5)	0.005 (4)	−0.017 (5)	0.004 (4)
C34	0.085 (8)	0.031 (5)	0.048 (6)	0.015 (5)	−0.029 (5)	−0.008 (4)
C37	0.104 (10)	0.043 (6)	0.056 (7)	0.020 (6)	−0.040 (7)	−0.007 (5)
C35	0.141 (13)	0.031 (5)	0.060 (7)	0.032 (6)	−0.055 (8)	−0.017 (5)
C36	0.21 (2)	0.067 (9)	0.075 (10)	0.075 (12)	−0.072 (12)	−0.023 (8)
C68	0.047 (5)	0.042 (5)	0.036 (5)	−0.015 (4)	0.005 (4)	0.005 (4)
C69	0.048 (5)	0.038 (5)	0.035 (5)	−0.002 (4)	−0.001 (4)	−0.010 (4)
C73	0.051 (5)	0.033 (4)	0.032 (4)	0.001 (4)	−0.003 (4)	0.005 (3)
C70	0.047 (6)	0.106 (10)	0.045 (6)	−0.013 (6)	0.002 (5)	−0.022 (6)
C71	0.041 (5)	0.132 (12)	0.062 (7)	0.006 (6)	−0.008 (6)	−0.038 (9)
C72	0.060 (6)	0.068 (7)	0.051 (6)	0.017 (6)	−0.008 (5)	−0.024 (5)
C56	0.046 (5)	0.043 (5)	0.030 (4)	0.002 (4)	0.004 (4)	−0.003 (4)
C57	0.058 (5)	0.024 (4)	0.029 (4)	−0.001 (3)	0.005 (4)	0.005 (3)
C58	0.076 (7)	0.032 (5)	0.041 (5)	−0.010 (5)	0.010 (5)	−0.005 (4)
C61	0.068 (7)	0.047 (6)	0.059 (7)	−0.016 (5)	0.018 (6)	−0.013 (5)
C59	0.144 (13)	0.040 (6)	0.056 (7)	−0.037 (7)	0.040 (8)	−0.020 (5)
C60	0.171 (17)	0.051 (7)	0.060 (8)	−0.060 (9)	0.029 (9)	−0.008 (6)
C1S	0.057 (7)	0.060 (7)	0.077 (8)	0.003 (5)	−0.007 (6)	0.019 (6)
C5S	0.094 (12)	0.062 (9)	0.146 (17)	0.009 (8)	−0.003 (11)	−0.005 (10)
C4S	0.076 (10)	0.041 (7)	0.25 (3)	−0.005 (6)	0.030 (13)	0.032 (11)
C2S	0.065 (8)	0.127 (14)	0.072 (10)	−0.005 (8)	0.006 (7)	0.031 (10)
C6S	0.097 (12)	0.102 (13)	0.101 (13)	0.011 (10)	0.028 (10)	0.038 (11)
C3S	0.082 (9)	0.055 (7)	0.114 (14)	−0.009 (6)	−0.005 (8)	0.021 (8)
C7S	0.067 (6)	0.051 (6)	0.039 (5)	0.010 (5)	0.004 (5)	0.016 (4)
C8S	0.082 (8)	0.050 (6)	0.040 (6)	0.019 (6)	0.007 (5)	0.010 (5)
C9S	0.102 (11)	0.065 (8)	0.052 (7)	−0.004 (7)	−0.005 (7)	−0.019 (6)
C10S	0.076 (8)	0.058 (6)	0.037 (5)	0.004 (6)	0.001 (5)	−0.001 (5)
C11S	0.077 (9)	0.103 (11)	0.048 (7)	0.019 (8)	0.004 (6)	−0.012 (7)
C12S	0.075 (9)	0.128 (14)	0.075 (10)	−0.009 (9)	0.003 (7)	−0.026 (9)
Cl1S	0.085 (3)	0.131 (4)	0.118 (4)	−0.001 (3)	−0.002 (3)	0.021 (3)
Cl2S	0.0616 (18)	0.170 (5)	0.068 (2)	0.012 (2)	−0.0020 (16)	0.030 (3)
N5	0.045 (4)	0.034 (4)	0.029 (3)	−0.002 (3)	0.001 (3)	0.001 (3)
N6	0.039 (4)	0.055 (5)	0.038 (4)	0.003 (3)	−0.004 (3)	−0.003 (4)
N7	0.051 (4)	0.031 (3)	0.024 (3)	0.002 (3)	−0.004 (3)	0.001 (3)
N8	0.049 (4)	0.035 (4)	0.026 (3)	0.001 (3)	−0.001 (3)	0.007 (3)
N9	0.047 (4)	0.030 (3)	0.027 (3)	−0.004 (3)	0.005 (3)	−0.003 (3)
N10	0.043 (4)	0.030 (4)	0.034 (4)	−0.010 (3)	−0.003 (3)	0.004 (3)
N11	0.056 (5)	0.051 (5)	0.036 (4)	0.008 (4)	−0.006 (4)	0.001 (4)
N12	0.055 (5)	0.063 (5)	0.028 (4)	−0.011 (4)	0.003 (3)	0.002 (4)
N13	0.163 (13)	0.070 (8)	0.071 (7)	0.059 (8)	−0.047 (8)	−0.023 (6)
N14	0.109 (9)	0.066 (7)	0.080 (8)	−0.043 (7)	0.026 (7)	−0.012 (6)
O1	0.077 (5)	0.059 (4)	0.033 (4)	−0.019 (4)	0.016 (3)	−0.015 (3)
O2	0.069 (5)	0.056 (4)	0.023 (3)	0.002 (3)	−0.007 (3)	−0.002 (3)
O3	0.136 (9)	0.099 (7)	0.038 (4)	−0.084 (7)	−0.013 (5)	0.015 (4)
O4	0.098 (7)	0.102 (7)	0.045 (4)	0.056 (6)	0.017 (4)	0.031 (5)

Geometric parameters (Å, º)

Mn1—N1	2.138 (6)	C22—C23	1.515 (17)
Mn1—N2	2.141 (6)	C22—N6	1.380 (13)
Mn1—N3	2.141 (6)	C23—H23A	0.9800
Mn1—N4	2.154 (6)	C23—H23B	0.9800
Mn1—N5	2.171 (8)	C23—H23C	0.9800
N1—C4	1.373 (9)	C24—C25	1.471 (13)
N1—C1	1.374 (10)	C24—N5	1.347 (11)
N2—C19	1.379 (10)	C24—N6	1.356 (12)
N2—C16	1.374 (10)	C25—H25A	0.9800
N3—C14	1.380 (10)	C25—H25B	0.9800
N3—C11	1.389 (10)	C25—H25C	0.9800
N4—C9	1.380 (10)	C44—C45	1.504 (13)
N4—C6	1.367 (10)	C44—N8	1.336 (12)
C4—C3	1.467 (9)	C44—O4	1.214 (12)
C4—C5	1.402 (10)	C45—C49	1.388 (13)
C1—C2	1.454 (11)	C45—C46	1.371 (14)
C1—C20	1.406 (11)	C49—H49	0.9500
C19—C18	1.453 (10)	C49—N12	1.344 (12)
C19—C20	1.385 (11)	C46—H46	0.9500
C16—C17	1.459 (10)	C46—C47	1.371 (16)
C16—C15	1.398 (11)	C47—H47	0.9500
C14—C13	1.452 (11)	C47—C48	1.361 (16)
C14—C15	1.406 (11)	C48—H48	0.9500
C11—C12	1.436 (11)	C48—N12	1.347 (14)
C11—C10	1.421 (11)	C32—C33	1.482 (13)
C9—C8	1.455 (11)	C32—N7	1.349 (11)
C9—C10	1.395 (11)	C32—O2	1.237 (11)
C6—C7	1.452 (11)	C33—C34	1.406 (13)
C6—C5	1.416 (11)	C33—C37	1.371 (14)
C3—H3	0.9500	C34—H34	0.9500
C3—C2	1.362 (11)	C34—C35	1.352 (15)
C2—H2	0.9500	C37—H37	0.9500
C18—H18	0.9500	C37—N13	1.391 (16)
C18—C17	1.349 (11)	C35—H35	0.9500
C17—H17	0.9500	C35—C36	1.376 (19)
C13—H13	0.9500	C36—H36	0.9500
C13—C12	1.352 (12)	C36—N13	1.360 (18)
C12—H12	0.9500	C68—C69	1.491 (13)
C8—H8	0.9500	C68—N10	1.341 (11)
C8—C7	1.362 (12)	C68—O3	1.226 (12)
C7—H7	0.9500	C69—C73	1.388 (13)
C5—C26	1.498 (11)	C69—C70	1.386 (14)
C20—C62	1.499 (10)	C73—H73	0.9500
C15—C50	1.497 (11)	C73—N11	1.349 (12)
C10—C38	1.505 (10)	C70—H70	0.9500
C38—C43	1.409 (12)	C70—C71	1.373 (18)
C38—C39	1.386 (12)	C71—H71	0.9500
C43—C42	1.394 (12)	C71—C72	1.396 (18)
C43—N8	1.427 (11)	C72—H72	0.9500
C42—H42	0.9500	C72—N11	1.329 (14)
C42—C41	1.389 (14)	C56—C57	1.488 (12)
C41—H41	0.9500	C56—N9	1.350 (11)
C41—C40	1.373 (14)	C56—O1	1.232 (11)
C40—H40	0.9500	C57—C58	1.408 (13)
C40—C39	1.392 (12)	C57—C61	1.365 (14)
C39—H39	0.9500	C58—H58	0.9500
C26—C31	1.406 (11)	C58—C59	1.362 (15)
C26—C27	1.400 (12)	C61—H61	0.9500
C31—C30	1.393 (11)	C61—N14	1.364 (15)
C31—N7	1.417 (11)	C59—H59	0.9500
C30—H30	0.9500	C59—C60	1.33 (2)
C30—C29	1.373 (13)	C60—H60	0.9500
C29—H29	0.9500	C60—N14	1.39 (2)
C29—C28	1.397 (14)	C1S—H1S	0.9500
C28—H28	0.9500	C1S—C5S	1.3900
C28—C27	1.388 (12)	C1S—C3S	1.3900
C27—H27	0.9500	C5S—H5S	0.9500
C62—C67	1.399 (11)	C5S—C4S	1.3900
C62—C63	1.391 (11)	C4S—C2S	1.3900
C67—C66	1.432 (11)	C4S—Cl1S	1.692 (8)
C67—N10	1.405 (11)	C2S—H2S	0.9500
C66—H66	0.9500	C2S—C6S	1.3900
C66—C65	1.385 (13)	C6S—H6S	0.9500
C65—H65	0.9500	C6S—C3S	1.3900
C65—C64	1.392 (14)	C3S—H3S	0.9500
C64—H64	0.9500	C7S—C8S	1.387 (16)
C64—C63	1.398 (12)	C7S—C10S	1.360 (15)
C63—H63	0.9500	C7S—Cl2S	1.740 (12)
C50—C55	1.409 (12)	C8S—H8S	0.9500
C50—C51	1.404 (12)	C8S—C9S	1.322 (19)
C55—C54	1.384 (11)	C9S—H9S	0.9500
C55—N9	1.417 (11)	C9S—C12S	1.38 (2)
C54—H54	0.9500	C10S—H10S	0.9500
C54—C53	1.399 (14)	C10S—C11S	1.366 (19)
C53—H53	0.9500	C11S—H11S	0.9500
C53—C52	1.395 (14)	C11S—C12S	1.41 (2)
C52—H52	0.9500	C12S—H12S	0.9500
C52—C51	1.382 (12)	N6—H6	0.8800
C51—H51	0.9500	N7—N11	3.098 (12)
C21—H21	0.9500	N8—H8A	0.8800
C21—C22	1.349 (15)	N9—H9	0.8800
C21—N5	1.374 (11)	N10—H10	0.8800
N1—Mn1—N2	86.9 (2)	C52—C51—H51	119.3
N1—Mn1—N3	150.0 (3)	C22—C21—H21	125.0
N1—Mn1—N4	85.5 (2)	C22—C21—N5	109.9 (9)
N1—Mn1—N5	98.1 (3)	N5—C21—H21	125.0
N2—Mn1—N4	148.9 (3)	C21—C22—C23	130.4 (11)
N2—Mn1—N5	101.4 (3)	C21—C22—N6	106.1 (9)
N3—Mn1—N2	85.3 (2)	N6—C22—C23	122.9 (11)
N3—Mn1—N4	86.4 (2)	C22—C23—H23A	109.5
N3—Mn1—N5	111.8 (3)	C22—C23—H23B	109.5
N4—Mn1—N5	109.5 (3)	C22—C23—H23C	109.5
C4—N1—Mn1	125.8 (5)	H23A—C23—H23B	109.5
C4—N1—C1	108.0 (6)	H23A—C23—H23C	109.5
C1—N1—Mn1	124.3 (5)	H23B—C23—H23C	109.5
C19—N2—Mn1	124.2 (5)	N5—C24—C25	127.4 (8)
C16—N2—Mn1	126.1 (5)	N5—C24—N6	109.0 (8)
C16—N2—C19	107.9 (6)	N6—C24—C25	123.6 (8)
C14—N3—Mn1	126.3 (5)	C24—C25—H25A	109.5
C14—N3—C11	106.7 (6)	C24—C25—H25B	109.5
C11—N3—Mn1	126.1 (5)	C24—C25—H25C	109.5
C9—N4—Mn1	126.5 (5)	H25A—C25—H25B	109.5
C6—N4—Mn1	125.9 (5)	H25A—C25—H25C	109.5
C6—N4—C9	106.9 (6)	H25B—C25—H25C	109.5
N1—C4—C3	109.0 (6)	N8—C44—C45	114.9 (8)
N1—C4—C5	126.0 (7)	O4—C44—C45	120.3 (9)
C5—C4—C3	125.0 (7)	O4—C44—N8	124.9 (9)
N1—C1—C2	108.7 (7)	C49—C45—C44	120.8 (8)
N1—C1—C20	125.9 (7)	C46—C45—C44	121.0 (8)
C20—C1—C2	125.4 (7)	C46—C45—C49	118.1 (9)
N2—C19—C18	108.3 (6)	C45—C49—H49	118.3
N2—C19—C20	126.4 (7)	N12—C49—C45	123.4 (9)
C20—C19—C18	125.3 (7)	N12—C49—H49	118.3
N2—C16—C17	108.7 (6)	C45—C46—H46	120.3
N2—C16—C15	125.4 (7)	C47—C46—C45	119.5 (10)
C15—C16—C17	125.9 (7)	C47—C46—H46	120.3
N3—C14—C13	108.9 (6)	C46—C47—H47	120.6
N3—C14—C15	124.8 (7)	C48—C47—C46	118.8 (10)
C15—C14—C13	126.2 (7)	C48—C47—H47	120.6
N3—C11—C12	109.4 (7)	C47—C48—H48	118.0
N3—C11—C10	125.2 (7)	N12—C48—C47	123.9 (10)
C10—C11—C12	125.3 (7)	N12—C48—H48	118.0
N4—C9—C8	109.3 (6)	N7—C32—C33	115.2 (8)
N4—C9—C10	125.8 (7)	O2—C32—C33	121.0 (8)
C10—C9—C8	124.9 (7)	O2—C32—N7	123.7 (9)
N4—C6—C7	110.0 (7)	C34—C33—C32	119.7 (8)
N4—C6—C5	125.7 (7)	C37—C33—C32	120.8 (9)
C5—C6—C7	124.2 (7)	C37—C33—C34	119.3 (9)
C4—C3—H3	126.8	C33—C34—H34	119.6
C2—C3—C4	106.4 (7)	C35—C34—C33	120.8 (10)
C2—C3—H3	126.8	C35—C34—H34	119.6
C1—C2—H2	126.1	C33—C37—H37	119.8
C3—C2—C1	107.9 (7)	C33—C37—N13	120.4 (11)
C3—C2—H2	126.1	N13—C37—H37	119.8
C19—C18—H18	126.0	C34—C35—H35	121.0
C17—C18—C19	108.0 (7)	C34—C35—C36	118.0 (11)
C17—C18—H18	126.0	C36—C35—H35	121.0
C16—C17—H17	126.5	C35—C36—H36	118.1
C18—C17—C16	107.1 (7)	N13—C36—C35	123.7 (13)
C18—C17—H17	126.5	N13—C36—H36	118.1
C14—C13—H13	126.2	N10—C68—C69	115.8 (8)
C12—C13—C14	107.5 (7)	O3—C68—C69	121.5 (9)
C12—C13—H13	126.2	O3—C68—N10	122.6 (9)
C11—C12—H12	126.3	C73—C69—C68	121.4 (8)
C13—C12—C11	107.5 (7)	C70—C69—C68	120.3 (9)
C13—C12—H12	126.3	C70—C69—C73	118.2 (9)
C9—C8—H8	126.5	C69—C73—H73	118.2
C7—C8—C9	107.0 (7)	N11—C73—C69	123.6 (9)
C7—C8—H8	126.5	N11—C73—H73	118.2
C6—C7—H7	126.6	C69—C70—H70	120.9
C8—C7—C6	106.8 (7)	C71—C70—C69	118.2 (11)
C8—C7—H7	126.6	C71—C70—H70	120.9
C4—C5—C6	125.4 (7)	C70—C71—H71	119.8
C4—C5—C26	118.2 (7)	C70—C71—C72	120.5 (11)
C6—C5—C26	116.3 (7)	C72—C71—H71	119.8
C1—C20—C62	115.4 (7)	C71—C72—H72	119.2
C19—C20—C1	126.5 (7)	N11—C72—C71	121.6 (11)
C19—C20—C62	118.0 (7)	N11—C72—H72	119.2
C16—C15—C14	126.4 (7)	N9—C56—C57	114.5 (8)
C16—C15—C50	116.8 (7)	O1—C56—C57	121.2 (8)
C14—C15—C50	116.7 (7)	O1—C56—N9	124.2 (9)
C11—C10—C38	116.6 (7)	C58—C57—C56	121.6 (8)
C9—C10—C11	126.5 (7)	C61—C57—C56	120.1 (8)
C9—C10—C38	116.7 (7)	C61—C57—C58	118.2 (9)
C43—C38—C10	119.6 (7)	C57—C58—H58	120.2
C39—C38—C10	121.6 (8)	C59—C58—C57	119.6 (11)
C39—C38—C43	118.7 (7)	C59—C58—H58	120.2
C38—C43—N8	117.7 (7)	C57—C61—H61	117.9
C42—C43—C38	120.5 (8)	N14—C61—C57	124.1 (11)
C42—C43—N8	121.8 (8)	N14—C61—H61	117.9
C43—C42—H42	120.8	C58—C59—H59	120.8
C41—C42—C43	118.4 (9)	C60—C59—C58	118.4 (12)
C41—C42—H42	120.8	C60—C59—H59	120.8
C42—C41—H41	118.8	C59—C60—H60	117.0
C40—C41—C42	122.3 (8)	C59—C60—N14	126.0 (11)
C40—C41—H41	118.8	N14—C60—H60	117.0
C41—C40—H40	120.7	C5S—C1S—H1S	120.0
C41—C40—C39	118.7 (9)	C5S—C1S—C3S	120.0
C39—C40—H40	120.7	C3S—C1S—H1S	120.0
C38—C39—C40	121.3 (8)	C1S—C5S—H5S	120.0
C38—C39—H39	119.4	C1S—C5S—C4S	120.0
C40—C39—H39	119.4	C4S—C5S—H5S	120.0
C31—C26—C5	120.8 (7)	C5S—C4S—Cl1S	122.5 (7)
C27—C26—C5	121.1 (7)	C2S—C4S—C5S	120.0
C27—C26—C31	118.1 (7)	C2S—C4S—Cl1S	117.4 (7)
C26—C31—N7	118.5 (7)	C4S—C2S—H2S	120.0
C30—C31—C26	120.9 (8)	C4S—C2S—C6S	120.0
C30—C31—N7	120.6 (7)	C6S—C2S—H2S	120.0
C31—C30—H30	120.1	C2S—C6S—H6S	120.0
C29—C30—C31	119.8 (8)	C3S—C6S—C2S	120.0
C29—C30—H30	120.1	C3S—C6S—H6S	120.0
C30—C29—H29	119.7	C1S—C3S—H3S	120.0
C30—C29—C28	120.5 (8)	C6S—C3S—C1S	120.0
C28—C29—H29	119.7	C6S—C3S—H3S	120.0
C29—C28—H28	120.2	C8S—C7S—Cl2S	119.6 (9)
C27—C28—C29	119.7 (9)	C10S—C7S—C8S	121.9 (11)
C27—C28—H28	120.2	C10S—C7S—Cl2S	118.5 (10)
C26—C27—H27	119.6	C7S—C8S—H8S	120.1
C28—C27—C26	120.9 (8)	C9S—C8S—C7S	119.8 (11)
C28—C27—H27	119.6	C9S—C8S—H8S	120.1
C67—C62—C20	120.0 (7)	C8S—C9S—H9S	119.7
C63—C62—C20	120.6 (7)	C8S—C9S—C12S	120.7 (13)
C63—C62—C67	119.4 (7)	C12S—C9S—H9S	119.7
C62—C67—C66	120.1 (8)	C7S—C10S—H10S	120.9
C62—C67—N10	118.7 (7)	C7S—C10S—C11S	118.3 (11)
N10—C67—C66	121.2 (8)	C11S—C10S—H10S	120.9
C67—C66—H66	120.8	C10S—C11S—H11S	119.9
C65—C66—C67	118.4 (8)	C10S—C11S—C12S	120.2 (12)
C65—C66—H66	120.8	C12S—C11S—H11S	119.9
C66—C65—H65	119.0	C9S—C12S—C11S	118.9 (14)
C66—C65—C64	121.9 (8)	C9S—C12S—H12S	120.5
C64—C65—H65	119.0	C11S—C12S—H12S	120.5
C65—C64—H64	120.6	C21—N5—Mn1	125.6 (6)
C65—C64—C63	118.9 (8)	C24—N5—Mn1	127.6 (6)
C63—C64—H64	120.6	C24—N5—C21	106.6 (8)
C62—C63—C64	121.2 (8)	C22—N6—H6	125.8
C62—C63—H63	119.4	C24—N6—C22	108.3 (8)
C64—C63—H63	119.4	C24—N6—H6	125.8
C55—C50—C15	121.4 (7)	C31—N7—H7A	117.9
C51—C50—C15	120.6 (8)	C32—N7—C31	124.2 (7)
C51—C50—C55	118.0 (7)	C32—N7—H7A	117.9
C50—C55—N9	118.3 (7)	C43—N8—H8A	115.8
C54—C55—C50	120.7 (8)	C44—N8—C43	128.4 (7)
C54—C55—N9	121.0 (8)	C44—N8—H8A	115.8
C55—C54—H54	119.8	C55—N9—H9	117.3
C55—C54—C53	120.4 (9)	C56—N9—C55	125.4 (8)
C53—C54—H54	119.8	C56—N9—H9	117.3
C54—C53—H53	120.2	C67—N10—H10	114.7
C52—C53—C54	119.6 (8)	C68—N10—C67	130.6 (7)
C52—C53—H53	120.2	C68—N10—H10	114.7
C53—C52—H52	120.1	C72—N11—C73	117.8 (9)
C51—C52—C53	119.8 (9)	C49—N12—C48	116.2 (9)
C51—C52—H52	120.1	C36—N13—C37	117.4 (12)
C50—C51—H51	119.3	C61—N14—C60	113.5 (12)
C52—C51—C50	121.5 (8)
Mn1—N1—C4—C3	163.1 (5)	C41—C40—C39—C38	2.0 (13)
Mn1—N1—C4—C5	−18.4 (11)	C39—C38—C43—C42	0.3 (12)
Mn1—N1—C1—C2	−163.2 (5)	C39—C38—C43—N8	179.7 (7)
Mn1—N1—C1—C20	18.9 (11)	C26—C31—C30—C29	0.5 (13)
Mn1—N2—C19—C18	164.8 (5)	C26—C31—N7—C32	118.2 (9)
Mn1—N2—C19—C20	−16.6 (11)	C31—C26—C27—C28	3.1 (12)
Mn1—N2—C16—C17	−163.8 (5)	C31—C30—C29—C28	0.8 (14)
Mn1—N2—C16—C15	17.8 (12)	C30—C31—N7—C32	−61.0 (12)
Mn1—N3—C14—C13	167.0 (5)	C30—C29—C28—C27	−0.1 (14)
Mn1—N3—C14—C15	−17.1 (12)	C29—C28—C27—C26	−1.9 (13)
Mn1—N3—C11—C12	−166.6 (6)	C27—C26—C31—C30	−2.5 (12)
Mn1—N3—C11—C10	17.3 (12)	C27—C26—C31—N7	178.4 (7)
Mn1—N4—C9—C8	169.2 (5)	C62—C67—C66—C65	0.3 (13)
Mn1—N4—C9—C10	−11.9 (11)	C62—C67—N10—C68	158.0 (9)
Mn1—N4—C6—C7	−168.4 (5)	C67—C62—C63—C64	3.5 (12)
Mn1—N4—C6—C5	16.3 (12)	C67—C66—C65—C64	0.4 (14)
N1—C4—C3—C2	0.8 (9)	C66—C67—N10—C68	−20.7 (14)
N1—C4—C5—C6	1.2 (14)	C66—C65—C64—C63	0.8 (13)
N1—C4—C5—C26	−175.0 (7)	C65—C64—C63—C62	−2.8 (13)
N1—C1—C2—C3	−1.3 (9)	C63—C62—C67—C66	−2.2 (12)
N1—C1—C20—C19	−2.0 (13)	C63—C62—C67—N10	179.2 (7)
N1—C1—C20—C62	173.4 (7)	C50—C55—C54—C53	−0.5 (13)
N2—C19—C18—C17	−0.3 (10)	C50—C55—N9—C56	128.5 (9)
N2—C19—C20—C1	0.8 (13)	C55—C50—C51—C52	2.6 (13)
N2—C19—C20—C62	−174.5 (7)	C55—C54—C53—C52	1.1 (14)
N2—C16—C17—C18	−1.5 (10)	C54—C55—N9—C56	−52.5 (13)
N2—C16—C15—C14	−1.2 (14)	C54—C53—C52—C51	0.1 (14)
N2—C16—C15—C50	175.9 (8)	C53—C52—C51—C50	−2.0 (13)
N3—C14—C13—C12	1.1 (10)	C51—C50—C55—C54	−1.3 (12)
N3—C14—C15—C16	0.7 (14)	C51—C50—C55—N9	177.7 (7)
N3—C14—C15—C50	−176.3 (7)	C21—C22—N6—C24	2.2 (12)
N3—C11—C12—C13	−2.2 (10)	C22—C21—N5—Mn1	−174.5 (7)
N3—C11—C10—C9	−4.3 (14)	C22—C21—N5—C24	0.2 (12)
N3—C11—C10—C38	170.1 (8)	C23—C22—N6—C24	−169.7 (13)
N4—C9—C8—C7	0.1 (9)	C25—C24—N5—Mn1	−5.7 (12)
N4—C9—C10—C11	1.3 (14)	C25—C24—N5—C21	179.7 (9)
N4—C9—C10—C38	−173.1 (7)	C25—C24—N6—C22	179.3 (9)
N4—C6—C7—C8	−2.4 (10)	C44—C45—C49—N12	177.9 (9)
N4—C6—C5—C4	−0.1 (14)	C44—C45—C46—C47	−179.8 (11)
N4—C6—C5—C26	176.2 (8)	C45—C44—N8—C43	−168.8 (8)
C4—N1—C1—C2	1.8 (9)	C45—C49—N12—C48	1.5 (15)
C4—N1—C1—C20	−176.1 (8)	C45—C46—C47—C48	2 (2)
C4—C3—C2—C1	0.3 (9)	C49—C45—C46—C47	−3.7 (17)
C4—C5—C26—C31	105.8 (9)	C46—C45—C49—N12	1.7 (15)
C4—C5—C26—C27	−73.7 (10)	C46—C47—C48—N12	1 (2)
C1—N1—C4—C3	−1.6 (9)	C47—C48—N12—C49	−2.9 (18)
C1—N1—C4—C5	176.8 (8)	C32—C33—C34—C35	177.9 (12)
C1—C20—C62—C67	−68.3 (10)	C32—C33—C37—N13	178.1 (13)
C1—C20—C62—C63	111.7 (9)	C33—C32—N7—C31	−163.5 (8)
C19—N2—C16—C17	1.3 (9)	C33—C34—C35—C36	0 (2)
C19—N2—C16—C15	−177.2 (8)	C33—C37—N13—C36	8 (3)
C19—C18—C17—C16	1.0 (10)	C34—C33—C37—N13	−7 (2)
C19—C20—C62—C67	107.5 (9)	C34—C35—C36—N13	0 (3)
C19—C20—C62—C63	−72.5 (10)	C37—C33—C34—C35	3 (2)
C16—N2—C19—C18	−0.6 (9)	C35—C36—N13—C37	−4 (3)
C16—N2—C19—C20	178.1 (8)	C68—C69—C73—N11	174.6 (9)
C16—C15—C50—C55	−65.6 (10)	C68—C69—C70—C71	−177.9 (12)
C16—C15—C50—C51	114.0 (9)	C69—C68—N10—C67	−165.4 (9)
C14—N3—C11—C12	2.9 (9)	C69—C73—N11—C72	3.2 (15)
C14—N3—C11—C10	−173.1 (8)	C69—C70—C71—C72	3 (2)
C14—C13—C12—C11	0.7 (10)	C73—C69—C70—C71	−2.0 (18)
C14—C15—C50—C55	111.7 (9)	C70—C69—C73—N11	−1.2 (15)
C14—C15—C50—C51	−68.7 (10)	C70—C71—C72—N11	−1 (2)
C11—N3—C14—C13	−2.5 (9)	C71—C72—N11—C73	−2.0 (17)
C11—N3—C14—C15	173.4 (8)	C56—C57—C58—C59	175.9 (11)
C11—C10—C38—C43	−68.7 (10)	C56—C57—C61—N14	179.8 (12)
C11—C10—C38—C39	113.0 (9)	C57—C56—N9—C55	−164.5 (8)
C9—N4—C6—C7	2.4 (9)	C57—C58—C59—C60	2 (2)
C9—N4—C6—C5	−172.8 (8)	C57—C61—N14—C60	6 (2)
C9—C8—C7—C6	1.3 (10)	C58—C57—C61—N14	−3.9 (18)
C9—C10—C38—C43	106.3 (9)	C58—C59—C60—N14	1 (3)
C9—C10—C38—C39	−72.0 (10)	C61—C57—C58—C59	−0.4 (17)
C6—N4—C9—C8	−1.6 (9)	C59—C60—N14—C61	−5 (3)
C6—N4—C9—C10	177.4 (8)	C1S—C5S—C4S—C2S	0.0
C6—C5—C26—C31	−70.7 (10)	C1S—C5S—C4S—Cl1S	177.2 (8)
C6—C5—C26—C27	109.7 (9)	C5S—C1S—C3S—C6S	0.0
C3—C4—C5—C6	179.4 (8)	C5S—C4S—C2S—C6S	0.0
C3—C4—C5—C26	3.2 (12)	C4S—C2S—C6S—C3S	0.0
C2—C1—C20—C19	−179.6 (8)	C2S—C6S—C3S—C1S	0.0
C2—C1—C20—C62	−4.2 (12)	C3S—C1S—C5S—C4S	0.0
C18—C19—C20—C1	179.2 (8)	C7S—C8S—C9S—C12S	−5 (2)
C18—C19—C20—C62	3.9 (12)	C7S—C10S—C11S—C12S	2 (2)
C17—C16—C15—C14	−179.3 (8)	C8S—C7S—C10S—C11S	−3.5 (18)
C17—C16—C15—C50	−2.3 (13)	C8S—C9S—C12S—C11S	3 (3)
C13—C14—C15—C16	175.9 (8)	C10S—C7S—C8S—C9S	4.8 (17)
C13—C14—C15—C50	−1.1 (12)	C10S—C11S—C12S—C9S	−2 (3)
C12—C11—C10—C9	−179.7 (8)	Cl1S—C4S—C2S—C6S	−177.3 (7)
C12—C11—C10—C38	−5.3 (12)	Cl2S—C7S—C8S—C9S	−175.1 (10)
C8—C9—C10—C11	−179.9 (8)	Cl2S—C7S—C10S—C11S	176.5 (10)
C8—C9—C10—C38	5.7 (12)	N5—C21—C22—C23	169.6 (14)
C7—C6—C5—C4	−174.7 (8)	N5—C21—C22—N6	−1.5 (13)
C7—C6—C5—C26	1.6 (12)	N5—C24—N6—C22	−2.1 (10)
C5—C4—C3—C2	−177.7 (8)	N6—C24—N5—Mn1	175.8 (5)
C5—C6—C7—C8	172.9 (8)	N6—C24—N5—C21	1.2 (10)
C5—C26—C31—C30	178.0 (8)	N7—C31—C30—C29	179.6 (8)
C5—C26—C31—N7	−1.1 (11)	N7—C32—C33—C34	37.1 (14)
C5—C26—C27—C28	−177.3 (8)	N7—C32—C33—C37	−148.0 (11)
C20—C1—C2—C3	176.6 (8)	N8—C43—C42—C41	−179.0 (8)
C20—C19—C18—C17	−179.0 (8)	N8—C44—C45—C49	34.5 (13)
C20—C62—C67—C66	177.8 (8)	N8—C44—C45—C46	−149.5 (10)
C20—C62—C67—N10	−0.9 (11)	N9—C55—C54—C53	−179.5 (8)
C20—C62—C63—C64	−176.5 (8)	N9—C56—C57—C58	36.3 (13)
C15—C16—C17—C18	177.0 (8)	N9—C56—C57—C61	−147.5 (10)
C15—C14—C13—C12	−174.7 (8)	N10—C67—C66—C65	178.9 (8)
C15—C50—C55—C54	178.3 (8)	N10—C68—C69—C73	39.6 (13)
C15—C50—C55—N9	−2.7 (12)	N10—C68—C69—C70	−144.7 (11)
C15—C50—C51—C52	−177.0 (8)	O1—C56—C57—C58	−140.0 (10)
C10—C11—C12—C13	173.8 (8)	O1—C56—C57—C61	36.2 (14)
C10—C9—C8—C7	−178.8 (8)	O1—C56—N9—C55	11.7 (15)
C10—C38—C43—C42	−178.1 (8)	O2—C32—C33—C34	−139.0 (11)
C10—C38—C43—N8	1.3 (11)	O2—C32—C33—C37	35.9 (16)
C10—C38—C39—C40	176.8 (8)	O2—C32—N7—C31	12.6 (15)
C38—C43—C42—C41	0.4 (13)	O3—C68—C69—C73	−138.5 (12)
C38—C43—N8—C44	159.6 (9)	O3—C68—C69—C70	37.2 (17)
C43—C38—C39—C40	−1.6 (13)	O3—C68—N10—C67	12.7 (18)
C43—C42—C41—C40	0.0 (14)	O4—C44—C45—C49	−145.3 (11)
C42—C43—N8—C44	−21.0 (14)	O4—C44—C45—C46	30.7 (16)
C42—C41—C40—C39	−1.2 (14)	O4—C44—N8—C43	11.0 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O2^i	0.88	2.05	2.858 (11)	153
N7—H7A···N11	0.88	2.24	3.094 (11)	164
N9—H9···N12	0.88	2.17	3.009 (10)	159
C5S—H5S···N14^ii	0.95	2.57	3.421 (16)	150
C36—H36···O3^ii	0.95	2.35	2.99 (2)	124
C60—H60···O4^iii	0.95	2.40	3.062 (18)	126

Symmetry codes: (i) −x+1, −y, z+1/2; (ii) −x+1/2, y+1/2, z−1/2; (iii) −x+1/2, y−1/2, z+1/2.