The mol­ecular structure of high-spin (S = ) manganese(II) phthalocyanine in tetra­butyl­ammonium bromido(phthalocyaninato)manganese(II)

The title complex salt, (C₁₆H₃₆N)[MnBr(C₃₂H₁₆N₈)] or (TBA)[Mn^IIBr(Pc)] (TBA is tetra­butyl­ammonium and Pc is phthalocyaninate), has been obtained as single crystals by the diffusion technique and its crystal structure was determined using X-ray diffraction. The high-spin (S = ) [Mn^IIBr(Pc)]⁻ macrocycle has a concave conformation, with an average equatorial Mn—N(Pc) bond length of 2.1187 (19) Å, an axial Mn—Br bond length of 2.5493 (7) Å and with the Mn^II cation displaced out of the 24-atom Pc plane by 0.894 (2) Å. The geometry of the Mn^IIN₄ fragment in [Mn^IIBr(Pc)]⁻ is similar to that of the high-spin (S = ) manganese(II) tetra­phenyl­porphyrin (TPP) in [Mn^II(1-MeIm)(TPP)] (1-MeIm is 1-methyl­imidazole).

Computing details

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Tetrabutylammonium bromido(phthalocyaninato)manganese(II)

Crystal data

(C16H36N)[MnBr(C32H16N8)]	F(000) = 1852
Mr = 889.83	Dx = 1.383 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.1149 (3) Å	Cell parameters from 7246 reflections
b = 13.9114 (3) Å	θ = 2.9–31.7°
c = 23.5614 (7) Å	µ = 1.29 mm^−1
β = 96.207 (2)°	T = 100 K
V = 4273.5 (13) Å^3	Block, black
Z = 4	0.40 × 0.31 × 0.23 mm

Data collection

Agilent Xcalibur Eos diffractometer	12813 independent reflections
Radiation source: Enhance (Mo) X-ray Source	9403 reflections with I > 2σ(I)
Detector resolution: 16.2060 pixels mm^-1	Rint = 0.030
ω scans	θmax = 31.8°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −19→15
Tmin = 0.816, Tmax = 1.000	k = −19→17
22788 measured reflections	l = −34→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0391P)^2 + 4.0067P] where P = (Fo^2 + 2Fc^2)/3
12813 reflections	(Δ/σ)max = 0.002
532 parameters	Δρmax = 1.18 e Å^−3
0 restraints	Δρmin = −0.63 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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

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

	x	y	z	Uiso*/Ueq
Br1	0.59247 (2)	0.41400 (2)	0.78250 (2)	0.01944 (6)
Mn1	0.48639 (3)	0.39798 (2)	0.86651 (2)	0.01350 (8)
N102	0.22962 (14)	0.42015 (13)	0.81032 (8)	0.0157 (4)
N104	0.46999 (15)	0.63715 (13)	0.90950 (8)	0.0160 (4)
N103	0.37246 (14)	0.50648 (13)	0.86119 (8)	0.0145 (4)
N101	0.35908 (14)	0.30515 (13)	0.84841 (8)	0.0144 (4)
N106	0.67652 (15)	0.37063 (13)	0.98080 (8)	0.0167 (4)
N105	0.55623 (15)	0.48550 (13)	0.93364 (8)	0.0154 (4)
C102	0.27896 (17)	0.49996 (15)	0.82916 (9)	0.0148 (4)
N108	0.43286 (15)	0.15363 (13)	0.88502 (8)	0.0158 (4)
N107	0.54421 (15)	0.28462 (13)	0.92059 (8)	0.0162 (4)
C127	0.66037 (18)	0.19488 (16)	0.97914 (10)	0.0162 (4)
C115	0.23506 (17)	0.59660 (15)	0.82076 (9)	0.0155 (4)
C101	0.26524 (17)	0.33148 (15)	0.82167 (9)	0.0138 (4)
C110	0.10428 (18)	0.23177 (16)	0.78239 (10)	0.0188 (5)
H110	0.0636	0.2846	0.7678	0.023*
C103	0.39022 (17)	0.60062 (15)	0.87605 (9)	0.0153 (4)
C128	0.58858 (17)	0.13112 (16)	0.95152 (10)	0.0157 (4)
C129	0.59395 (19)	0.03303 (17)	0.96296 (10)	0.0192 (5)
H129	0.5454	−0.0104	0.9443	0.023*
C104	0.54403 (17)	0.58281 (15)	0.93672 (9)	0.0153 (4)
C116	0.30512 (18)	0.65961 (15)	0.85048 (9)	0.0155 (4)
C113	0.22424 (18)	0.07370 (16)	0.82788 (10)	0.0181 (5)
H113	0.2640	0.0211	0.8436	0.022*
C120	0.14548 (18)	0.63036 (16)	0.79040 (10)	0.0169 (4)
H120	0.0983	0.5875	0.7701	0.020*
C107	0.51599 (17)	0.19034 (16)	0.91522 (10)	0.0153 (4)
C112	0.12575 (19)	0.06020 (17)	0.80000 (11)	0.0208 (5)
H112	0.0979	−0.0028	0.7965	0.025*
C122	0.68901 (18)	0.54478 (16)	0.99601 (9)	0.0157 (4)
C106	0.62936 (17)	0.29126 (16)	0.95967 (10)	0.0159 (4)
C105	0.64116 (17)	0.45893 (16)	0.96944 (9)	0.0158 (4)
C125	0.73979 (19)	0.72961 (17)	1.03204 (10)	0.0195 (5)
H125	0.7586	0.7927	1.0446	0.023*
C109	0.20250 (17)	0.24534 (15)	0.80957 (10)	0.0150 (4)
C124	0.80136 (19)	0.65189 (17)	1.05157 (10)	0.0204 (5)
H124	0.8614	0.6632	1.0770	0.024*
C121	0.62727 (17)	0.62314 (16)	0.97613 (9)	0.0156 (4)
C123	0.77661 (19)	0.55821 (17)	1.03452 (10)	0.0186 (5)
H123	0.8177	0.5053	1.0485	0.022*
C108	0.35994 (17)	0.20745 (15)	0.85649 (9)	0.0149 (4)
C114	0.26167 (17)	0.16720 (16)	0.83170 (9)	0.0153 (4)
C118	0.19668 (19)	0.79142 (16)	0.82120 (10)	0.0207 (5)
H118	0.1820	0.8583	0.8214	0.025*
C126	0.65106 (18)	0.71647 (16)	0.99439 (10)	0.0178 (5)
H126	0.6086	0.7692	0.9817	0.021*
C132	0.73958 (18)	0.16229 (17)	1.01853 (10)	0.0192 (5)
H132	0.7882	0.2057	1.0371	0.023*
C117	0.28654 (19)	0.75827 (16)	0.85132 (10)	0.0187 (5)
H117	0.3336	0.8011	0.8717	0.022*
C111	0.06756 (18)	0.13785 (17)	0.77722 (11)	0.0212 (5)
H111	0.0014	0.1264	0.7577	0.025*
C131	0.7453 (2)	0.06412 (17)	1.02985 (10)	0.0223 (5)
H131	0.7990	0.0399	1.0563	0.027*
C119	0.12706 (19)	0.72929 (17)	0.79061 (10)	0.0193 (5)
H119	0.0669	0.7545	0.7699	0.023*
C130	0.6730 (2)	0.00063 (17)	1.00273 (11)	0.0223 (5)
H130	0.6778	−0.0659	1.0116	0.027*
N201	0.30116 (15)	0.82234 (14)	0.32510 (8)	0.0189 (4)
C213	0.19487 (17)	0.78921 (17)	0.33641 (10)	0.0184 (5)
H21A	0.1448	0.8391	0.3220	0.022*
H21B	0.1931	0.7849	0.3782	0.022*
C205	0.31445 (19)	0.92286 (17)	0.35111 (11)	0.0217 (5)
H20A	0.2586	0.9644	0.3334	0.026*
H20B	0.3067	0.9185	0.3924	0.026*
C209	0.31212 (19)	0.82244 (17)	0.26135 (10)	0.0198 (5)
H20C	0.3837	0.8397	0.2561	0.024*
H20D	0.3000	0.7563	0.2466	0.024*
C214	0.15963 (19)	0.69331 (17)	0.31008 (11)	0.0215 (5)
H21C	0.2163	0.6461	0.3155	0.026*
H21D	0.1402	0.7014	0.2686	0.026*
C201	0.38327 (19)	0.75368 (18)	0.35141 (11)	0.0227 (5)
H20E	0.4512	0.7823	0.3473	0.027*
H20F	0.3782	0.6933	0.3291	0.027*
C210	0.2410 (2)	0.88988 (18)	0.22557 (10)	0.0235 (5)
H21E	0.2611	0.9573	0.2343	0.028*
H21F	0.1698	0.8808	0.2349	0.028*
C215	0.0677 (2)	0.65651 (19)	0.33840 (11)	0.0256 (5)
H21G	0.0888	0.6466	0.3796	0.031*
H21H	0.0133	0.7062	0.3348	0.031*
C202	0.37942 (19)	0.72844 (19)	0.41398 (10)	0.0235 (5)
H20G	0.3163	0.6914	0.4185	0.028*
H20H	0.3781	0.7880	0.4369	0.028*
C216	0.0237 (2)	0.56285 (19)	0.31277 (12)	0.0283 (6)
H21Y	−0.0347	0.5430	0.3327	0.043*
H21Z	0.0766	0.5128	0.3170	0.043*
H21K	0.0008	0.5724	0.2722	0.043*
C211	0.2462 (2)	0.86987 (19)	0.16212 (10)	0.0250 (5)
H21I	0.3181	0.8765	0.1534	0.030*
H21J	0.2242	0.8029	0.1535	0.030*
C203	0.4736 (2)	0.6688 (2)	0.43512 (12)	0.0319 (6)
H20I	0.4765	0.6114	0.4105	0.038*
H20J	0.5361	0.7074	0.4318	0.038*
C212	0.1787 (2)	0.9381 (2)	0.12456 (12)	0.0346 (7)
H21L	0.1841	0.9231	0.0843	0.052*
H21M	0.2012	1.0044	0.1325	0.052*
H21N	0.1073	0.9308	0.1325	0.052*
C207	0.4168 (3)	1.0780 (2)	0.36194 (15)	0.0463 (8)
H20K	0.4791	1.1094	0.3504	0.056*
H20L	0.3565	1.1101	0.3411	0.056*
C204	0.4727 (2)	0.6366 (2)	0.49670 (12)	0.0355 (7)
H20M	0.5343	0.5985	0.5083	0.053*
H20N	0.4116	0.5974	0.5001	0.053*
H20O	0.4716	0.6932	0.5214	0.053*
C206	0.4170 (2)	0.9711 (2)	0.34413 (13)	0.0364 (7)
H20X	0.4310	0.9663	0.3038	0.044*
H20Z	0.4725	0.9369	0.3679	0.044*
C208	0.4137 (3)	1.0921 (3)	0.42434 (17)	0.0572 (11)
H20P	0.4154	1.1610	0.4331	0.086*
H20Q	0.4731	1.0605	0.4453	0.086*
H20R	0.3505	1.0640	0.4358	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02006 (12)	0.02007 (11)	0.01884 (11)	−0.00066 (9)	0.00502 (8)	0.00029 (9)
Mn1	0.01314 (16)	0.01323 (15)	0.01375 (16)	−0.00009 (12)	−0.00029 (12)	0.00073 (12)
N102	0.0150 (9)	0.0156 (8)	0.0159 (9)	−0.0001 (7)	−0.0004 (7)	0.0021 (7)
N104	0.0180 (9)	0.0143 (8)	0.0156 (9)	−0.0005 (7)	0.0015 (7)	0.0002 (7)
N103	0.0146 (9)	0.0131 (8)	0.0154 (9)	−0.0003 (7)	−0.0003 (7)	0.0004 (7)
N101	0.0141 (9)	0.0134 (8)	0.0153 (9)	0.0008 (7)	−0.0008 (7)	0.0031 (7)
N106	0.0160 (9)	0.0178 (9)	0.0160 (9)	−0.0011 (8)	0.0004 (7)	−0.0001 (7)
N105	0.0164 (9)	0.0164 (9)	0.0130 (9)	−0.0003 (7)	0.0001 (7)	−0.0001 (7)
C102	0.0163 (11)	0.0157 (10)	0.0125 (10)	0.0016 (8)	0.0028 (8)	0.0028 (8)
N108	0.0157 (9)	0.0147 (8)	0.0167 (9)	0.0001 (7)	−0.0001 (7)	0.0018 (7)
N107	0.0161 (9)	0.0156 (9)	0.0164 (9)	−0.0007 (7)	−0.0002 (7)	0.0008 (7)
C127	0.0158 (11)	0.0172 (10)	0.0156 (11)	0.0014 (9)	0.0020 (8)	0.0009 (8)
C115	0.0179 (11)	0.0139 (10)	0.0150 (10)	0.0013 (8)	0.0032 (8)	0.0010 (8)
C101	0.0132 (10)	0.0164 (10)	0.0116 (10)	−0.0006 (8)	0.0001 (8)	0.0011 (8)
C110	0.0162 (11)	0.0169 (10)	0.0226 (12)	0.0015 (9)	−0.0011 (9)	0.0015 (9)
C103	0.0166 (10)	0.0157 (10)	0.0141 (10)	0.0010 (8)	0.0037 (8)	0.0012 (8)
C128	0.0144 (10)	0.0180 (10)	0.0148 (10)	0.0018 (9)	0.0021 (8)	0.0001 (8)
C129	0.0208 (12)	0.0181 (10)	0.0182 (11)	0.0010 (9)	0.0001 (9)	0.0011 (9)
C104	0.0170 (10)	0.0147 (10)	0.0145 (10)	−0.0005 (9)	0.0026 (8)	0.0006 (8)
C116	0.0176 (11)	0.0156 (10)	0.0135 (10)	0.0011 (9)	0.0022 (8)	0.0014 (8)
C113	0.0173 (11)	0.0149 (10)	0.0213 (11)	−0.0001 (9)	−0.0011 (9)	0.0027 (9)
C120	0.0158 (11)	0.0178 (10)	0.0171 (11)	0.0015 (9)	0.0013 (9)	0.0007 (9)
C107	0.0147 (10)	0.0162 (10)	0.0150 (10)	0.0014 (8)	0.0017 (8)	0.0015 (8)
C112	0.0197 (12)	0.0154 (10)	0.0265 (13)	−0.0040 (9)	−0.0008 (10)	0.0022 (9)
C122	0.0185 (11)	0.0172 (10)	0.0113 (10)	−0.0021 (9)	0.0018 (8)	−0.0006 (8)
C106	0.0153 (10)	0.0165 (10)	0.0153 (11)	0.0009 (9)	−0.0008 (8)	0.0020 (8)
C105	0.0159 (11)	0.0189 (10)	0.0123 (10)	−0.0005 (9)	0.0005 (8)	−0.0010 (8)
C125	0.0230 (12)	0.0190 (11)	0.0164 (11)	−0.0033 (9)	0.0021 (9)	−0.0040 (9)
C109	0.0155 (10)	0.0140 (10)	0.0156 (10)	−0.0003 (8)	0.0015 (8)	0.0010 (8)
C124	0.0194 (12)	0.0261 (12)	0.0150 (11)	−0.0024 (10)	−0.0007 (9)	−0.0024 (9)
C121	0.0167 (11)	0.0182 (10)	0.0122 (10)	−0.0004 (9)	0.0029 (8)	−0.0004 (8)
C123	0.0200 (11)	0.0213 (11)	0.0142 (11)	0.0000 (9)	0.0002 (9)	0.0007 (9)
C108	0.0149 (10)	0.0148 (10)	0.0149 (10)	0.0003 (8)	0.0009 (8)	0.0000 (8)
C114	0.0145 (10)	0.0163 (10)	0.0148 (10)	−0.0012 (8)	−0.0004 (8)	0.0013 (8)
C118	0.0240 (12)	0.0147 (10)	0.0239 (12)	0.0062 (9)	0.0053 (10)	0.0017 (9)
C126	0.0204 (12)	0.0180 (10)	0.0152 (11)	0.0003 (9)	0.0025 (9)	−0.0006 (9)
C132	0.0188 (11)	0.0221 (11)	0.0159 (11)	0.0018 (9)	−0.0019 (9)	0.0000 (9)
C117	0.0199 (11)	0.0163 (10)	0.0197 (12)	0.0024 (9)	0.0021 (9)	−0.0017 (9)
C111	0.0146 (11)	0.0220 (11)	0.0259 (13)	−0.0022 (9)	−0.0033 (9)	0.0008 (10)
C131	0.0229 (12)	0.0248 (12)	0.0185 (11)	0.0072 (10)	−0.0015 (9)	0.0046 (10)
C119	0.0183 (11)	0.0220 (11)	0.0181 (11)	0.0061 (9)	0.0036 (9)	0.0035 (9)
C130	0.0262 (13)	0.0168 (11)	0.0230 (12)	0.0043 (10)	−0.0008 (10)	0.0054 (9)
N201	0.0173 (10)	0.0232 (10)	0.0163 (10)	0.0024 (8)	0.0018 (8)	0.0007 (8)
C213	0.0149 (11)	0.0247 (11)	0.0159 (11)	0.0018 (9)	0.0023 (9)	−0.0007 (9)
C205	0.0211 (12)	0.0244 (11)	0.0196 (12)	−0.0005 (10)	0.0023 (9)	−0.0031 (10)
C209	0.0204 (12)	0.0255 (12)	0.0143 (11)	0.0038 (10)	0.0056 (9)	0.0002 (9)
C214	0.0190 (12)	0.0252 (12)	0.0204 (12)	0.0019 (10)	0.0023 (9)	0.0000 (10)
C201	0.0167 (11)	0.0294 (12)	0.0217 (12)	0.0063 (10)	0.0010 (9)	0.0011 (10)
C210	0.0233 (12)	0.0299 (13)	0.0174 (11)	0.0052 (10)	0.0033 (9)	0.0016 (10)
C215	0.0260 (13)	0.0280 (13)	0.0227 (13)	−0.0037 (11)	0.0021 (10)	−0.0004 (10)
C202	0.0205 (12)	0.0305 (13)	0.0191 (12)	0.0035 (10)	−0.0002 (9)	0.0023 (10)
C216	0.0302 (14)	0.0242 (12)	0.0302 (14)	−0.0012 (11)	0.0011 (11)	0.0022 (11)
C211	0.0316 (14)	0.0277 (12)	0.0158 (12)	0.0009 (11)	0.0028 (10)	−0.0014 (10)
C203	0.0200 (13)	0.0446 (16)	0.0300 (15)	0.0055 (12)	−0.0026 (11)	0.0072 (13)
C212	0.0395 (17)	0.0442 (16)	0.0189 (13)	0.0032 (14)	−0.0025 (12)	0.0025 (12)
C207	0.046 (2)	0.0458 (18)	0.0456 (19)	−0.0177 (16)	−0.0014 (16)	0.0013 (15)
C204	0.0346 (16)	0.0405 (16)	0.0299 (15)	0.0091 (13)	−0.0033 (12)	0.0089 (13)
C206	0.0332 (16)	0.0436 (17)	0.0333 (16)	−0.0110 (14)	0.0084 (13)	−0.0115 (13)
C208	0.045 (2)	0.067 (2)	0.064 (2)	−0.0260 (19)	0.0255 (18)	−0.027 (2)

Geometric parameters (Å, º)

Br1—Mn1	2.5493 (7)	C132—C131	1.392 (3)
Mn1—N107	2.1158 (19)	C132—H132	0.9500
Mn1—N101	2.1174 (19)	C117—H117	0.9500
Mn1—N103	2.1180 (18)	C111—H111	0.9500
Mn1—N105	2.1236 (19)	C131—C130	1.399 (4)
N102—C101	1.336 (3)	C131—H131	0.9500
N102—C102	1.337 (3)	C119—H119	0.9500
N104—C104	1.338 (3)	C130—H130	0.9500
N104—C103	1.340 (3)	N201—C213	1.519 (3)
N103—C103	1.369 (3)	N201—C201	1.521 (3)
N103—C102	1.372 (3)	N201—C209	1.524 (3)
N101—C101	1.370 (3)	N201—C205	1.529 (3)
N101—C108	1.372 (3)	C213—C214	1.522 (3)
N106—C105	1.330 (3)	C213—H21A	0.9900
N106—C106	1.335 (3)	C213—H21B	0.9900
N105—C104	1.366 (3)	C205—C206	1.528 (4)
N105—C105	1.373 (3)	C205—H20A	0.9900
C102—C115	1.467 (3)	C205—H20B	0.9900
N108—C107	1.337 (3)	C209—C210	1.514 (3)
N108—C108	1.337 (3)	C209—H20C	0.9900
N107—C107	1.365 (3)	C209—H20D	0.9900
N107—C106	1.372 (3)	C214—C215	1.528 (3)
C127—C132	1.392 (3)	C214—H21C	0.9900
C127—C128	1.401 (3)	C214—H21D	0.9900
C127—C106	1.461 (3)	C201—C202	1.522 (3)
C115—C120	1.389 (3)	C201—H20E	0.9900
C115—C116	1.401 (3)	C201—H20F	0.9900
C101—C109	1.464 (3)	C210—C211	1.529 (3)
C110—C109	1.388 (3)	C210—H21E	0.9900
C110—C111	1.393 (3)	C210—H21F	0.9900
C110—H110	0.9500	C215—C216	1.523 (4)
C103—C116	1.462 (3)	C215—H21G	0.9900
C128—C129	1.391 (3)	C215—H21H	0.9900
C128—C107	1.463 (3)	C202—C203	1.527 (3)
C129—C130	1.395 (3)	C202—H20G	0.9900
C129—H129	0.9500	C202—H20H	0.9900
C104—C121	1.466 (3)	C216—H21Y	0.9800
C116—C117	1.394 (3)	C216—H21Z	0.9800
C113—C114	1.390 (3)	C216—H21K	0.9800
C113—C112	1.397 (3)	C211—C212	1.516 (4)
C113—H113	0.9500	C211—H21I	0.9900
C120—C119	1.397 (3)	C211—H21J	0.9900
C120—H120	0.9500	C203—C204	1.520 (4)
C112—C111	1.396 (3)	C203—H20I	0.9900
C112—H112	0.9500	C203—H20J	0.9900
C122—C123	1.397 (3)	C212—H21L	0.9800
C122—C121	1.407 (3)	C212—H21M	0.9800
C122—C105	1.458 (3)	C212—H21N	0.9800
C125—C126	1.397 (3)	C207—C208	1.488 (5)
C125—C124	1.397 (3)	C207—C206	1.546 (4)
C125—H125	0.9500	C207—H20K	0.9900
C109—C114	1.403 (3)	C207—H20L	0.9900
C124—C123	1.392 (3)	C204—H20M	0.9800
C124—H124	0.9500	C204—H20N	0.9800
C121—C126	1.393 (3)	C204—H20O	0.9800
C123—H123	0.9500	C206—H20X	0.9900
C108—C114	1.467 (3)	C206—H20Z	0.9900
C118—C117	1.387 (3)	C208—H20P	0.9800
C118—C119	1.399 (3)	C208—H20Q	0.9800
C118—H118	0.9500	C208—H20R	0.9800
C126—H126	0.9500
N107—Mn1—N101	83.69 (7)	C112—C111—H111	119.2
N107—Mn1—N103	140.48 (8)	C132—C131—C130	120.8 (2)
N101—Mn1—N103	83.50 (7)	C132—C131—H131	119.6
N107—Mn1—N105	83.17 (7)	C130—C131—H131	119.6
N101—Mn1—N105	140.07 (7)	C120—C119—C118	120.4 (2)
N103—Mn1—N105	83.12 (7)	C120—C119—H119	119.8
N107—Mn1—Br1	110.04 (6)	C118—C119—H119	119.8
N101—Mn1—Br1	112.43 (5)	C129—C130—C131	121.4 (2)
N103—Mn1—Br1	109.42 (5)	C129—C130—H130	119.3
N105—Mn1—Br1	107.49 (6)	C131—C130—H130	119.3
C101—N102—C102	123.66 (19)	C213—N201—C201	111.15 (18)
C104—N104—C103	123.19 (19)	C213—N201—C209	111.06 (18)
C103—N103—C102	108.74 (18)	C201—N201—C209	105.32 (18)
C103—N103—Mn1	124.55 (15)	C213—N201—C205	105.91 (18)
C102—N103—Mn1	124.64 (15)	C201—N201—C205	111.47 (19)
C101—N101—C108	108.78 (18)	C209—N201—C205	112.04 (18)
C101—N101—Mn1	125.38 (14)	N201—C213—C214	116.00 (19)
C108—N101—Mn1	125.57 (15)	N201—C213—H21A	108.3
C105—N106—C106	123.5 (2)	C214—C213—H21A	108.3
C104—N105—C105	109.03 (19)	N201—C213—H21B	108.3
C104—N105—Mn1	124.34 (15)	C214—C213—H21B	108.3
C105—N105—Mn1	123.99 (15)	H21A—C213—H21B	107.4
N102—C102—N103	127.6 (2)	C206—C205—N201	114.9 (2)
N102—C102—C115	123.2 (2)	C206—C205—H20A	108.5
N103—C102—C115	109.15 (19)	N201—C205—H20A	108.5
C107—N108—C108	123.46 (19)	C206—C205—H20B	108.5
C107—N107—C106	108.65 (18)	N201—C205—H20B	108.5
C107—N107—Mn1	125.76 (15)	H20A—C205—H20B	107.5
C106—N107—Mn1	124.53 (15)	C210—C209—N201	115.55 (19)
C132—C127—C128	121.3 (2)	C210—C209—H20C	108.4
C132—C127—C106	132.1 (2)	N201—C209—H20C	108.4
C128—C127—C106	106.6 (2)	C210—C209—H20D	108.4
C120—C115—C116	121.2 (2)	N201—C209—H20D	108.4
C120—C115—C102	132.6 (2)	H20C—C209—H20D	107.5
C116—C115—C102	106.21 (19)	C213—C214—C215	109.6 (2)
N102—C101—N101	128.0 (2)	C213—C214—H21C	109.8
N102—C101—C109	122.7 (2)	C215—C214—H21C	109.8
N101—C101—C109	109.19 (18)	C213—C214—H21D	109.8
C109—C110—C111	117.6 (2)	C215—C214—H21D	109.8
C109—C110—H110	121.2	H21C—C214—H21D	108.2
C111—C110—H110	121.2	N201—C201—C202	116.3 (2)
N104—C103—N103	127.9 (2)	N201—C201—H20E	108.2
N104—C103—C116	122.83 (19)	C202—C201—H20E	108.2
N103—C103—C116	109.30 (19)	N201—C201—H20F	108.2
C129—C128—C127	120.9 (2)	C202—C201—H20F	108.2
C129—C128—C107	133.0 (2)	H20E—C201—H20F	107.4
C127—C128—C107	106.09 (19)	C209—C210—C211	110.0 (2)
C128—C129—C130	117.7 (2)	C209—C210—H21E	109.7
C128—C129—H129	121.1	C211—C210—H21E	109.7
C130—C129—H129	121.1	C209—C210—H21F	109.7
N104—C104—N105	128.1 (2)	C211—C210—H21F	109.7
N104—C104—C121	122.6 (2)	H21E—C210—H21F	108.2
N105—C104—C121	109.23 (19)	C216—C215—C214	113.4 (2)
C117—C116—C115	121.1 (2)	C216—C215—H21G	108.9
C117—C116—C103	132.3 (2)	C214—C215—H21G	108.9
C115—C116—C103	106.56 (19)	C216—C215—H21H	108.9
C114—C113—C112	117.3 (2)	C214—C215—H21H	108.9
C114—C113—H113	121.4	H21G—C215—H21H	107.7
C112—C113—H113	121.4	C201—C202—C203	109.3 (2)
C115—C120—C119	117.9 (2)	C201—C202—H20G	109.8
C115—C120—H120	121.0	C203—C202—H20G	109.8
C119—C120—H120	121.0	C201—C202—H20H	109.8
N108—C107—N107	127.8 (2)	C203—C202—H20H	109.8
N108—C107—C128	122.5 (2)	H20G—C202—H20H	108.3
N107—C107—C128	109.52 (19)	C215—C216—H21Y	109.5
C111—C112—C113	121.1 (2)	C215—C216—H21Z	109.5
C111—C112—H112	119.5	H21Y—C216—H21Z	109.5
C113—C112—H112	119.5	C215—C216—H21K	109.5
C123—C122—C121	121.0 (2)	H21Y—C216—H21K	109.5
C123—C122—C105	132.3 (2)	H21Z—C216—H21K	109.5
C121—C122—C105	106.6 (2)	C212—C211—C210	111.8 (2)
N106—C106—N107	128.1 (2)	C212—C211—H21I	109.3
N106—C106—C127	122.7 (2)	C210—C211—H21I	109.3
N107—C106—C127	109.14 (19)	C212—C211—H21J	109.3
N106—C105—N105	127.9 (2)	C210—C211—H21J	109.3
N106—C105—C122	123.1 (2)	H21I—C211—H21J	107.9
N105—C105—C122	109.03 (19)	C204—C203—C202	112.4 (2)
C126—C125—C124	121.3 (2)	C204—C203—H20I	109.1
C126—C125—H125	119.3	C202—C203—H20I	109.1
C124—C125—H125	119.3	C204—C203—H20J	109.1
C110—C109—C114	121.0 (2)	C202—C203—H20J	109.1
C110—C109—C101	132.5 (2)	H20I—C203—H20J	107.8
C114—C109—C101	106.56 (19)	C211—C212—H21L	109.5
C123—C124—C125	121.4 (2)	C211—C212—H21M	109.5
C123—C124—H124	119.3	H21L—C212—H21M	109.5
C125—C124—H124	119.3	C211—C212—H21N	109.5
C126—C121—C122	121.2 (2)	H21L—C212—H21N	109.5
C126—C121—C104	132.8 (2)	H21M—C212—H21N	109.5
C122—C121—C104	106.05 (19)	C208—C207—C206	113.3 (3)
C124—C123—C122	117.5 (2)	C208—C207—H20K	108.9
C124—C123—H123	121.2	C206—C207—H20K	108.9
C122—C123—H123	121.2	C208—C207—H20L	108.9
N108—C108—N101	128.2 (2)	C206—C207—H20L	108.9
N108—C108—C114	122.42 (19)	H20K—C207—H20L	107.7
N101—C108—C114	109.21 (19)	C203—C204—H20M	109.5
C113—C114—C109	121.6 (2)	C203—C204—H20N	109.5
C113—C114—C108	132.2 (2)	H20M—C204—H20N	109.5
C109—C114—C108	106.21 (19)	C203—C204—H20O	109.5
C117—C118—C119	121.9 (2)	H20M—C204—H20O	109.5
C117—C118—H118	119.0	H20N—C204—H20O	109.5
C119—C118—H118	119.0	C205—C206—C207	111.4 (3)
C121—C126—C125	117.5 (2)	C205—C206—H20X	109.3
C121—C126—H126	121.3	C207—C206—H20X	109.3
C125—C126—H126	121.3	C205—C206—H20Z	109.3
C131—C132—C127	117.9 (2)	C207—C206—H20Z	109.3
C131—C132—H132	121.0	H20X—C206—H20Z	108.0
C127—C132—H132	121.0	C207—C208—H20P	109.5
C118—C117—C116	117.4 (2)	C207—C208—H20Q	109.5
C118—C117—H117	121.3	H20P—C208—H20Q	109.5
C116—C117—H117	121.3	C207—C208—H20R	109.5
C110—C111—C112	121.5 (2)	H20P—C208—H20R	109.5
C110—C111—H111	119.2	H20Q—C208—H20R	109.5