Bis(μ-cantharidinato)bis­[(1,10-phenanthroline)manganese(II)] hexa­hydrate

The title compound {systematic name: bis­(μ-2,3-dimethyl-7-oxobicyclo­[2.2.1]heptane-2,3-dicarboxyl­ato)bis­[(1,10-phenanthroline)manganese(II)] hexa­hydrate}, [Mn₂(C₁₀H₁₂O₅)₂(C₁₂H₈N₂)₂]·6H₂O, comprises centrosymmetric dinuclear neutral mol­ecules in which two Mn^II centers are bridged by a single carboxyl­ate group of each of two cantharidinate ligands, together with water molecules. In the complex, each Mn^II atom is in a distorted octa­hedral geometry, being coordinated by two N atoms of one 1,10-phenanthroline ligand, three O atoms from one cantharidinate dianion and one carboxylate O atom from another cantharidinate dianion. Adjacent mol­ecules link to each other through hydrogen bonds involving solvent water mol­ecules and carboxyl­ate groups, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.074
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

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Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   C20     ..       5.60 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
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   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

bis(µ-2,3-dimethyl-7-oxobicyclo[2.2.1]heptane-2,3- dicarboxylato)bis[(1,10-phenanthroline)manganese(II)] hexahydrate

Crystal data

[Mn2(C10H12O5)2(C12H8N2)2]·6H2O	F(000) = 2088.00
Mr = 1002.79	Dx = 1.515 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 17413 reflections
a = 17.806 (5) Å	θ = 3.0–27.5°
b = 20.600 (5) Å	µ = 0.65 mm^−1
c = 11.982 (3) Å	T = 298 K
β = 90.812 (11)°	Needle, yellow
V = 4395 (2) Å^3	0.30 × 0.15 × 0.10 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3904 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.029
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −23→23
Tmin = 0.830, Tmax = 0.937	k = −26→26
21189 measured reflections	l = −15→14
5033 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[0.0003Fo^2 + σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.074	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.35 e Å^−3
5033 reflections	Δρmin = −0.34 e Å^−3
303 parameters

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Mn1	0.241000 (10)	0.199050 (10)	0.66256 (2)	0.02785 (6)
O1	0.27975 (6)	0.12197 (6)	0.56117 (9)	0.0343 (2)
O2	0.28038 (6)	0.09050 (6)	0.38385 (9)	0.0455 (3)
O3	0.17367 (6)	0.24311 (5)	0.53552 (8)	0.0299 (2)
O4	0.17555 (6)	0.22806 (6)	0.35272 (8)	0.0338 (2)
O5	0.13254 (6)	0.12974 (5)	0.65226 (6)	0.0281 (2)
O6	0.000000 (10)	0.29861 (12)	0.250000 (10)	0.0930 (9)
O7	0.000000 (10)	0.47324 (10)	0.250000 (10)	0.0642 (6)
O8	0.43323 (8)	0.07894 (6)	0.36334 (12)	0.0589 (4)
O9	0.43373 (8)	0.10863 (9)	0.58903 (12)	0.0714 (5)
N1	0.27147 (6)	0.14483 (6)	0.82519 (10)	0.0309 (3)
N2	0.16934 (6)	0.24152 (6)	0.79571 (9)	0.0282 (3)
C1	0.32145 (10)	0.09838 (9)	0.84055 (13)	0.0414 (4)
C2	0.33484 (11)	0.06794 (9)	0.94276 (14)	0.0473 (5)
C3	0.29435 (11)	0.08682 (8)	1.03268 (13)	0.0426 (4)
C4	0.24000 (9)	0.13520 (8)	1.02118 (12)	0.0329 (4)
C5	0.19501 (10)	0.15837 (9)	1.11146 (12)	0.0378 (4)
C6	0.14336 (10)	0.20472 (9)	1.09595 (12)	0.0375 (4)
C7	0.13074 (9)	0.23361 (8)	0.98846 (12)	0.0309 (3)
C8	0.07725 (10)	0.28202 (9)	0.96785 (12)	0.0389 (4)
C9	0.07090 (10)	0.30905 (9)	0.86346 (13)	0.0422 (4)
C10	0.11869 (10)	0.28751 (8)	0.77998 (12)	0.0359 (4)
C11	0.17556 (8)	0.21388 (6)	0.89842 (11)	0.0263 (3)
C12	0.23003 (8)	0.16342 (6)	0.91417 (11)	0.0272 (3)
C13	0.24742 (9)	0.10079 (6)	0.47205 (12)	0.0289 (3)
C14	0.16239 (9)	0.08531 (6)	0.47822 (11)	0.0267 (3)
C15	0.14330 (9)	0.06695 (6)	0.60028 (11)	0.0296 (3)
C16	0.06492 (10)	0.03735 (8)	0.61249 (12)	0.0372 (4)
C17	0.01408 (9)	0.09706 (8)	0.59338 (12)	0.0350 (4)
C18	0.07212 (8)	0.15092 (8)	0.57799 (11)	0.0269 (3)
C19	0.11037 (8)	0.14838 (6)	0.46227 (10)	0.0247 (3)
C20	0.15695 (8)	0.21127 (6)	0.44957 (11)	0.0251 (3)
C21	0.05506 (9)	0.14505 (8)	0.36363 (12)	0.0328 (4)
C22	0.14496 (10)	0.03072 (8)	0.39478 (12)	0.0387 (4)
H1	0.3494	0.0852	0.7796	0.050*
H2	0.3708	0.0353	0.9494	0.057*
H3	0.3029	0.0674	1.1018	0.051*
H5	0.2020	0.1407	1.1823	0.045*
H6	0.1150	0.2185	1.1561	0.045*
H8	0.0461	0.2959	1.0247	0.047*
H9	0.0354	0.3411	0.8487	0.051*
H10	0.1147	0.3065	0.7097	0.043*
H15	0.1827	0.0411	0.6370	0.036*
H18	0.0529	0.1941	0.5965	0.032*
H161	0.0555	0.0041	0.5567	0.045*
H162	0.0582	0.0191	0.6863	0.045*
H171	−0.0174	0.0919	0.5273	0.042*
H172	−0.0172	0.1053	0.6574	0.042*
H211	0.0189	0.1114	0.3766	0.039*
H212	0.0819	0.1356	0.2966	0.039*
H213	0.0297	0.1860	0.3557	0.039*
H221	0.1743	−0.0069	0.4138	0.046*
H222	0.1572	0.0448	0.3209	0.046*
H223	0.0925	0.0201	0.3975	0.046*
H601	0.0230	0.3250	0.3010	0.112*
H701	0.0200	0.4481	0.3040	0.078*
H801	0.3826	0.0823	0.3665	0.071*
H802	0.4438	0.0423	0.3225	0.071*
H901	0.3835	0.1141	0.5812	0.086*
H902	0.4526	0.0941	0.5222	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.02837 (12)	0.03242 (12)	0.02283 (11)	−0.00451 (10)	0.00119 (8)	−0.00046 (9)
O1	0.0252 (5)	0.0417 (6)	0.0360 (5)	−0.0008 (4)	−0.0013 (4)	−0.0090 (4)
O2	0.0343 (6)	0.0666 (8)	0.0359 (5)	−0.0013 (5)	0.0099 (5)	−0.0121 (5)
O3	0.0355 (6)	0.0313 (5)	0.0228 (4)	−0.0075 (4)	−0.0021 (4)	−0.0006 (4)
O4	0.0363 (6)	0.0438 (6)	0.0214 (4)	−0.0124 (5)	0.0009 (4)	0.0044 (4)
O5	0.0299 (5)	0.0343 (5)	0.0202 (4)	−0.0047 (4)	−0.0013 (4)	0.0005 (4)
O6	0.115 (2)	0.0718 (17)	0.0920 (18)	0.0000	−0.0127 (16)	0.0000
O7	0.0614 (13)	0.0582 (13)	0.0732 (13)	0.0000	0.0089 (11)	0.0000
O8	0.0407 (8)	0.0600 (9)	0.0763 (9)	−0.0020 (6)	0.0130 (6)	−0.0050 (7)
O9	0.0403 (8)	0.1151 (13)	0.0587 (8)	0.0111 (8)	−0.0062 (6)	−0.0096 (8)
N1	0.0335 (7)	0.0339 (7)	0.0254 (5)	0.0007 (5)	0.0013 (5)	−0.0022 (5)
N2	0.0309 (7)	0.0311 (6)	0.0226 (5)	−0.0024 (5)	−0.0002 (4)	0.0007 (5)
C1	0.0432 (10)	0.0433 (10)	0.0378 (8)	0.0083 (8)	0.0025 (7)	−0.0031 (7)
C2	0.0524 (11)	0.0390 (10)	0.0504 (10)	0.0123 (8)	−0.0070 (8)	0.0027 (8)
C3	0.0532 (11)	0.0394 (9)	0.0348 (8)	−0.0029 (8)	−0.0084 (7)	0.0088 (7)
C4	0.0381 (9)	0.0346 (8)	0.0258 (6)	−0.0086 (7)	−0.0029 (6)	0.0038 (6)
C5	0.0440 (10)	0.0481 (10)	0.0213 (6)	−0.0107 (8)	0.0009 (6)	0.0056 (6)
C6	0.0391 (9)	0.0504 (10)	0.0230 (6)	−0.0096 (8)	0.0069 (6)	−0.0027 (6)
C7	0.0299 (8)	0.0372 (8)	0.0256 (6)	−0.0070 (6)	0.0035 (5)	−0.0050 (6)
C8	0.0343 (9)	0.0470 (9)	0.0355 (8)	−0.0006 (7)	0.0081 (6)	−0.0105 (7)
C9	0.0379 (9)	0.0446 (10)	0.0441 (9)	0.0095 (7)	−0.0027 (7)	−0.0061 (7)
C10	0.0422 (9)	0.0361 (9)	0.0292 (7)	0.0037 (7)	−0.0034 (6)	0.0001 (6)
C11	0.0268 (7)	0.0307 (7)	0.0214 (6)	−0.0073 (6)	0.0003 (5)	−0.0028 (5)
C12	0.0291 (7)	0.0296 (7)	0.0230 (6)	−0.0071 (6)	−0.0002 (5)	−0.0009 (5)
C13	0.0282 (8)	0.0274 (7)	0.0311 (7)	0.0025 (6)	0.0007 (6)	−0.0013 (6)
C14	0.0271 (7)	0.0283 (7)	0.0245 (6)	−0.0037 (5)	−0.0007 (5)	−0.0020 (5)
C15	0.0338 (8)	0.0286 (7)	0.0263 (6)	−0.0043 (6)	−0.0034 (6)	0.0039 (6)
C16	0.0394 (9)	0.0399 (9)	0.0324 (7)	−0.0135 (7)	0.0004 (6)	0.0061 (6)
C17	0.0292 (8)	0.0477 (9)	0.0282 (7)	−0.0101 (7)	0.0032 (6)	0.0039 (7)
C18	0.0237 (7)	0.0347 (8)	0.0224 (6)	−0.0023 (6)	0.0010 (5)	0.0004 (6)
C19	0.0234 (7)	0.0313 (7)	0.0193 (5)	−0.0041 (5)	−0.0004 (5)	0.0016 (5)
C20	0.0215 (7)	0.0319 (8)	0.0219 (6)	0.0013 (5)	−0.0014 (5)	0.0039 (5)
C21	0.0277 (8)	0.0442 (9)	0.0262 (6)	−0.0076 (7)	−0.0046 (5)	0.0031 (6)
C22	0.0420 (10)	0.0374 (9)	0.0365 (8)	−0.0041 (7)	−0.0010 (7)	−0.0089 (7)

Geometric parameters (Å, º)

Mn1—O1	2.1206 (11)	C16—C17	1.542 (2)
Mn1—O3	2.1276 (10)	C17—C18	1.529 (2)
Mn1—O4^i	2.1222 (11)	C18—C19	1.5543 (18)
Mn1—O5	2.4032 (11)	C19—C20	1.547 (2)
Mn1—N1	2.3042 (12)	C19—C21	1.5292 (19)
Mn1—N2	2.2353 (11)	O6—H601	0.911
O1—C13	1.2824 (18)	O6—H601^ii	0.911
O2—C13	1.2344 (18)	O7—H701	0.899
O3—C20	1.2533 (16)	O7—H701^ii	0.899
O4—C20	1.2597 (16)	O8—H801	0.906
O5—C15	1.4495 (17)	O8—H802	0.920
O5—C18	1.4535 (17)	O9—H901	0.905
N1—C1	1.318 (2)	O9—H902	0.923
N1—C12	1.3602 (18)	C1—H1	0.930
N2—C10	1.320 (2)	C2—H2	0.930
N2—C11	1.3591 (17)	C3—H3	0.930
C1—C2	1.393 (2)	C5—H5	0.930
C2—C3	1.362 (2)	C6—H6	0.930
C3—C4	1.395 (2)	C8—H8	0.930
C4—C5	1.437 (2)	C9—H9	0.930
C4—C12	1.4167 (19)	C10—H10	0.930
C5—C6	1.337 (2)	C15—H15	0.980
C6—C7	1.434 (2)	C16—H161	0.970
C7—C8	1.399 (2)	C16—H162	0.970
C7—C11	1.411 (2)	C17—H171	0.970
C8—C9	1.372 (2)	C17—H172	0.970
C9—C10	1.395 (2)	C18—H18	0.980
C11—C12	1.432 (2)	C21—H211	0.960
C13—C14	1.550 (2)	C21—H212	0.960
C14—C15	1.5530 (19)	C21—H213	0.960
C14—C19	1.605 (2)	C22—H221	0.960
C14—C22	1.534 (2)	C22—H222	0.960
C15—C16	1.532 (2)	C22—H223	0.960
O1···O9	2.7710 (17)	C10···H9^xiv	3.317
O2···O8	2.7466 (18)	C10···H801^i	3.206
O2···C2^iii	3.475 (2)	C12···H221^xi	3.374
O4···C5^iv	3.2506 (18)	C13···H2^iii	3.575
O4···C6^iv	3.1584 (17)	C13···H801	2.761
O6···O7	3.597 (3)	C13···H901	2.751
O6···O9^i	2.949 (2)	C15···H222^xi	3.511
O6···O9^v	2.949 (2)	C16···H161^xviii	3.051
O6···C21	3.575 (2)	C16···H162^xiv	3.303
O6···C21^ii	3.575 (2)	C16···H171^xviii	3.251
O7···O6	3.597 (3)	C16···H172^xiv	3.217
O7···O8^vi	2.836 (2)	C16···H211^xviii	3.412
O7···O8^vii	2.836 (2)	C16···H222^xi	3.418
O7···O9^i	2.809 (2)	C16···H223^xviii	3.044
O7···O9^v	2.809 (2)	C17···H161^xviii	3.008
O8···O2	2.7466 (18)	C17···H162^xiv	3.361
O8···O7^viii	2.836 (2)	C17···H172^xiv	2.990
O8···O9	2.772 (2)	C17···H223^xviii	3.073
O8···C9^i	3.565 (2)	C18···H172^xiv	3.461
O8···C9^ix	3.367 (2)	C20···H6^iv	3.587
O8···C10^i	3.366 (2)	C21···H5^iv	3.425
O9···O1	2.7710 (17)	C21···H6^iv	3.113
O9···O6^i	2.949 (2)	C21···H6^xiv	3.391
O9···O7^i	2.809 (2)	C21···H211^ii	3.224
O9···O8	2.772 (2)	C21···H212^ii	3.088
O9···C13	3.587 (2)	C21···H213^ii	3.128
N1···C6^x	3.572 (2)	C22···H5^iv	3.567
N2···C5^x	3.354 (2)	C22···H15^iii	3.499
C2···O2^xi	3.475 (2)	C22···H162^iii	3.093
C3···C8^x	3.540 (2)	C22···H171^xviii	3.531
C3···C9^x	3.438 (2)	H1···O7^i	2.965
C4···C7^x	3.553 (2)	H1···O9	2.793
C4···C11^x	3.580 (2)	H221···N1^iii	3.499
C5···O4^xii	3.2506 (18)	H221···C1^iii	3.355
C5···N2^x	3.354 (2)	H221···C2^iii	3.138
C5···C11^x	3.501 (2)	H221···C3^iii	3.037
C6···O4^xii	3.1584 (17)	H221···C4^iii	3.157
C6···N1^x	3.572 (2)	H221···C12^iii	3.374
C6···C12^x	3.533 (2)	H221···H2^iii	3.567
C7···C4^x	3.553 (2)	H221···H3^iii	3.426
C7···C12^x	3.453 (2)	H221···H15^iii	3.396
C8···C3^x	3.540 (2)	H221···H162^iii	3.406
C9···O8^i	3.565 (2)	H221···H171^xviii	3.380
C9···O8^xiii	3.367 (2)	H221···H172^xviii	3.548
C9···C3^x	3.438 (2)	H222···C5^iv	3.503
C10···O8^i	3.366 (2)	H222···C15^iii	3.511
C11···C4^x	3.580 (2)	H222···C16^iii	3.418
C11···C5^x	3.501 (2)	H222···H5^iv	2.708
C12···C6^x	3.533 (2)	H222···H15^iii	2.868
C12···C7^x	3.453 (2)	H222···H162^iii	2.712
C13···O9	3.587 (2)	H223···C16^xviii	3.044
C21···O6	3.575 (2)	H223···C17^xviii	3.073
C21···C21^ii	3.333 (2)	H223···H161^xviii	2.745
Mn1···H901	3.244	H223···H162^xviii	2.965
O1···H801	3.095	H223···H162^iii	2.717
O1···H901	1.867	H223···H171^xviii	2.820
O1···H902	3.173	H223···H172^xviii	2.980
O2···H2^iii	3.145	H601···O4	3.421
O2···H3^iv	3.442	H601···O7	3.139
O2···H5^iv	2.959	H601···O9^i	2.042
O2···H801	1.842	H601···O9^v	3.276
O2···H802	3.170	H601···C8^xiv	3.433
O2···H901	3.013	H601···H1^i	3.095
O2···H902	3.466	H601···H6^iv	3.255
O3···H901^i	3.407	H601···H6^xiv	3.340
O4···H5^iv	2.767	H601···H8^iv	3.395
O4···H6^iv	2.584	H601···H8^xiv	2.511
O4···H601	3.421	H601···H213	2.941
O4···H901^i	3.512	H601···H213^ii	3.545
O5···H172^xiv	3.131	H601···H701	2.535
O6···H6^iv	2.872	H601···H701^ii	2.926
O6···H6^xiv	2.872	H601···H901^i	2.504
O6···H8^iv	2.833	H601···H902^i	2.725
O6···H8^xiv	2.833	H701···O6	3.165
O6···H213	2.693	H701···O8^vi	3.193
O6···H213^ii	2.693	H701···O8^vii	3.469
O6···H701	3.165	H701···O9^i	1.912
O6···H701^ii	3.165	H701···O9^v	3.201
O6···H901^i	3.393	H701···C1^i	3.468
O6···H901^v	3.393	H701···H1^i	2.636
O7···H1^i	2.965	H701···H1^v	3.123
O7···H1^v	2.965	H701···H2^v	3.217
O7···H2^i	3.346	H701···H601	2.535
O7···H2^v	3.346	H701···H601^ii	2.926
O7···H601	3.139	H701···H802^vi	2.381
O7···H601^ii	3.139	H701···H802^vii	2.552
O7···H801^vi	3.384	H701···H901^i	2.533
O7···H801^vii	3.384	H701···H902^i	2.303
O7···H802^vi	1.951	H801···O1	3.095
O7···H802^vii	1.951	H801···O2	1.842
O7···H901^i	3.392	H801···O7^viii	3.384
O7···H901^v	3.392	H801···O9	2.857
O7···H902^i	3.166	H801···C2^iii	3.340
O7···H902^v	3.166	H801···C10^i	3.206
O8···H2^iii	2.807	H801···C13	2.761
O8···H9^i	3.085	H801···H2^iii	2.628
O8···H9^ix	2.462	H801···H3^iv	3.470
O8···H10^i	2.654	H801···H9^i	3.373
O8···H701^viii	3.193	H801···H9^ix	3.155
O8···H701^xv	3.469	H801···H10^i	2.467
O8···H802^xvi	3.235	H801···H901	2.654
O8···H901	2.861	H801···H902	2.242
O8···H902	1.954	H802···O2	3.170
O9···H1	2.793	H802···O7^viii	1.951
O9···H2^iii	3.577	H802···O8^xvi	3.235
O9···H8^ix	2.917	H802···O9	3.480
O9···H9^ix	3.577	H802···C2^iii	3.328
O9···H601^i	2.042	H802···H1^iii	3.156
O9···H601^xvii	3.276	H802···H2^iii	2.572
O9···H701^i	1.912	H802···H9^i	3.183
O9···H701^xvii	3.201	H802···H9^ix	2.917
O9···H801	2.857	H802···H10^i	3.305
O9···H802	3.480	H802···H701^viii	2.381
N1···H6^x	3.471	H802···H701^xv	2.552
N1···H221^xi	3.499	H802···H802^xvi	2.670
N2···H5^x	3.345	H802···H902	2.622
C1···H8^x	3.579	H901···Mn1	3.244
C1···H221^xi	3.355	H901···O1	1.867
C1···H701^i	3.468	H901···O2	3.013
C1···H901	3.328	H901···O3^i	3.407
C2···H8^x	3.535	H901···O4^i	3.512
C2···H221^xi	3.138	H901···O6^i	3.393
C2···H801^xi	3.340	H901···O7^i	3.392
C2···H802^xi	3.328	H901···O8	2.861
C3···H15^xi	3.540	H901···C1	3.328
C3···H221^xi	3.037	H901···C13	2.751
C4···H221^xi	3.157	H901···H1	2.533
C5···H212^xii	3.054	H901···H2^iii	3.465
C5···H222^xii	3.503	H901···H8^ix	3.512
C6···H171^xiv	3.538	H901···H601^i	2.504
C6···H211^xiv	3.489	H901···H701^i	2.533
C6···H212^xii	3.013	H901···H801	2.654
C6···H213^xiv	3.168	H902···O1	3.173
C7···H18^xiv	3.506	H902···O2	3.466
C7···H171^xiv	3.552	H902···O7^i	3.166
C7···H213^xiv	3.573	H902···O8	1.954
C8···H18^xiv	3.032	H902···C8^ix	3.449
C8···H213^xiv	3.482	H902···C9^ix	3.485
C8···H601^xiv	3.433	H902···H2^xix	3.383
C8···H902^xiii	3.449	H902···H2^iii	3.156
C9···H3^x	3.416	H902···H8^ix	2.812
C9···H9^xiv	3.216	H902···H9^ix	2.891
C9···H10^xiv	3.407	H902···H601^i	2.725
C9···H18^xiv	3.275	H902···H701^i	2.303
C9···H902^xiii	3.485	H902···H801	2.242
C10···H3^x	3.581	H902···H802	2.622
C10···H5^x	3.542
O1—Mn1—O3	95.40 (4)	O5—C18—C19	101.90 (10)
O1—Mn1—O4^i	104.27 (4)	C17—C18—C19	112.87 (12)
O1—Mn1—N1	92.69 (4)	C14—C19—C18	100.39 (10)
O1—Mn1—N2	153.59 (4)	C14—C19—C20	112.35 (11)
O3—Mn1—O4^i	91.41 (4)	C14—C19—C21	114.83 (11)
O3—Mn1—N1	159.30 (4)	C18—C19—C20	107.57 (11)
O3—Mn1—N2	91.27 (4)	C18—C19—C21	113.92 (11)
O4^i—Mn1—N1	105.02 (4)	C20—C19—C21	107.57 (11)
O4^i—Mn1—N2	101.08 (4)	O3—C20—O4	123.42 (13)
O4^i—Mn1—O5	168.22 (4)	O3—C20—C19	118.61 (11)
O5—Mn1—O1	78.08 (4)	O4—C20—C19	117.96 (11)
O5—Mn1—O3	76.85 (4)	H601—O6—H601^ii	106.6
O5—Mn1—N1	86.27 (4)	H701—O7—H701^ii	109.5
O5—Mn1—N2	78.63 (4)	H801—O8—H802	107.2
N1—Mn1—N2	73.51 (4)	H901—O9—H902	108.8
Mn1—O1—C13	125.87 (9)	N1—C1—H1	118.1
Mn1—O3—C20	119.31 (9)	C2—C1—H1	118.1
Mn1^i—O4—C20	117.86 (9)	C1—C2—H2	120.6
C15—O5—C18	96.08 (10)	C3—C2—H2	120.6
Mn1—N1—C1	128.35 (10)	C2—C3—H3	120.0
Mn1—N1—C12	113.74 (9)	C4—C3—H3	120.0
C1—N1—C12	117.89 (12)	C4—C5—H5	119.3
Mn1—N2—C10	125.09 (9)	C6—C5—H5	119.3
Mn1—N2—C11	116.25 (9)	C5—C6—H6	119.3
C10—N2—C11	118.48 (12)	C7—C6—H6	119.3
N1—C1—C2	123.80 (15)	C7—C8—H8	120.1
C1—C2—C3	118.75 (17)	C9—C8—H8	120.1
C2—C3—C4	120.03 (15)	C8—C9—H9	120.6
C3—C4—C5	123.82 (14)	C10—C9—H9	120.6
C3—C4—C12	117.42 (13)	N2—C10—H10	118.4
C5—C4—C12	118.75 (14)	C9—C10—H10	118.4
C4—C5—C6	121.50 (14)	O5—C15—H15	112.9
C5—C6—C7	121.34 (14)	C14—C15—H15	112.9
C6—C7—C8	123.53 (14)	C16—C15—H15	112.9
C6—C7—C11	118.96 (14)	C15—C16—H161	111.4
C8—C7—C11	117.49 (13)	C15—C16—H162	111.4
C7—C8—C9	119.83 (15)	C17—C16—H161	111.4
C8—C9—C10	118.77 (16)	C17—C16—H162	111.4
N2—C10—C9	123.27 (14)	H161—C16—H162	109.5
N2—C11—C7	122.14 (13)	C16—C17—H171	111.4
N2—C11—C12	118.01 (12)	C16—C17—H172	111.4
C7—C11—C12	119.84 (12)	C18—C17—H171	111.4
N1—C12—C4	122.10 (13)	C18—C17—H172	111.4
N1—C12—C11	118.35 (12)	H171—C17—H172	109.5
C4—C12—C11	119.54 (12)	O5—C18—H18	113.1
O1—C13—O2	123.92 (14)	C17—C18—H18	113.1
O1—C13—C14	117.23 (12)	C19—C18—H18	113.1
O2—C13—C14	118.82 (13)	C19—C21—H211	109.5
C13—C14—C15	108.78 (11)	C19—C21—H212	109.5
C13—C14—C19	112.96 (11)	C19—C21—H213	109.5
C13—C14—C22	107.97 (12)	H211—C21—H212	109.5
C15—C14—C19	100.11 (10)	H211—C21—H213	109.5
C15—C14—C22	112.98 (12)	H212—C21—H213	109.5
C19—C14—C22	113.88 (11)	C14—C22—H221	109.5
O5—C15—C14	102.67 (10)	C14—C22—H222	109.5
O5—C15—C16	100.84 (11)	C14—C22—H223	109.5
C14—C15—C16	113.50 (12)	H221—C22—H222	109.5
C15—C16—C17	101.65 (12)	H221—C22—H223	109.5
C16—C17—C18	101.55 (12)	H222—C22—H223	109.5
O5—C18—C17	101.77 (11)
O1—Mn1—O3—C20	16.28 (10)	C5—C4—C12—N1	178.81 (14)
O3—Mn1—O1—C13	−22.09 (12)	C5—C4—C12—C11	−0.2 (2)
O1—Mn1—O4^i—C20^i	51.85 (11)	C12—C4—C5—C6	1.3 (2)
O4^i—Mn1—O1—C13	−114.93 (12)	C4—C5—C6—C7	−0.3 (2)
O1—Mn1—N1—C1	23.69 (14)	C5—C6—C7—C8	179.74 (17)
O1—Mn1—N1—C12	−154.53 (9)	C5—C6—C7—C11	−2.0 (2)
N1—Mn1—O1—C13	138.83 (12)	C6—C7—C8—C9	177.27 (16)
O1—Mn1—N2—C10	−117.50 (13)	C6—C7—C11—N2	−176.56 (14)
O1—Mn1—N2—C11	57.55 (15)	C6—C7—C11—C12	3.1 (2)
N2—Mn1—O1—C13	81.81 (15)	C8—C7—C11—N2	1.8 (2)
O3—Mn1—O4^i—C20^i	−44.09 (10)	C8—C7—C11—C12	−178.55 (14)
O4^i—Mn1—O3—C20	120.76 (10)	C11—C7—C8—C9	−1.0 (2)
O3—Mn1—N1—C1	136.71 (14)	C7—C8—C9—C10	−0.3 (2)
O3—Mn1—N1—C12	−41.52 (17)	C8—C9—C10—N2	1.0 (2)
N1—Mn1—O3—C20	−96.27 (15)	N2—C11—C12—N1	−1.4 (2)
O3—Mn1—N2—C10	−12.65 (12)	N2—C11—C12—C4	177.65 (13)
O3—Mn1—N2—C11	162.40 (10)	C7—C11—C12—N1	178.95 (13)
N2—Mn1—O3—C20	−138.13 (10)	C7—C11—C12—C4	−2.0 (2)
O4^i—Mn1—N1—C1	−81.85 (14)	O1—C13—C14—C15	−27.46 (17)
O4^i—Mn1—N1—C12	99.92 (10)	O1—C13—C14—C19	82.75 (15)
N1—Mn1—O4^i—C20^i	148.65 (10)	O1—C13—C14—C22	−150.41 (13)
O4^i—Mn1—N2—C10	79.03 (13)	O2—C13—C14—C15	150.55 (13)
O4^i—Mn1—N2—C11	−105.92 (10)	O2—C13—C14—C19	−99.24 (15)
N2—Mn1—O4^i—C20^i	−135.65 (10)	O2—C13—C14—C22	27.60 (18)
N1—Mn1—N2—C10	−178.41 (13)	C13—C14—C15—O5	83.87 (13)
N1—Mn1—N2—C11	−3.36 (9)	C13—C14—C15—C16	−168.19 (12)
N2—Mn1—N1—C1	−179.21 (14)	C13—C14—C19—C18	−116.63 (12)
N2—Mn1—N1—C12	2.57 (9)	C13—C14—C19—C20	−2.59 (14)
Mn1—O1—C13—O2	132.53 (13)	C13—C14—C19—C21	120.76 (13)
Mn1—O1—C13—C14	−49.57 (17)	C15—C14—C19—C18	−1.11 (13)
Mn1—O3—C20—O4	−119.08 (13)	C15—C14—C19—C20	112.92 (11)
Mn1—O3—C20—C19	61.55 (15)	C15—C14—C19—C21	−123.72 (12)
Mn1^i—O4—C20—O3	14.25 (19)	C19—C14—C15—O5	−34.76 (13)
Mn1^i—O4—C20—C19	−166.39 (9)	C19—C14—C15—C16	73.17 (14)
C15—O5—C18—C17	57.46 (11)	C22—C14—C15—O5	−156.24 (12)
C15—O5—C18—C19	−59.25 (12)	C22—C14—C15—C16	−48.31 (17)
C18—O5—C15—C14	58.77 (12)	C22—C14—C19—C18	119.73 (12)
C18—O5—C15—C16	−58.56 (11)	C22—C14—C19—C20	−126.24 (12)
Mn1—N1—C1—C2	−179.01 (13)	C22—C14—C19—C21	−2.89 (17)
Mn1—N1—C12—C4	179.37 (11)	O5—C15—C16—C17	37.15 (12)
Mn1—N1—C12—C11	−1.60 (16)	C14—C15—C16—C17	−71.92 (14)
C1—N1—C12—C4	0.9 (2)	C15—C16—C17—C18	−2.06 (13)
C1—N1—C12—C11	179.98 (11)	C16—C17—C18—O5	−33.60 (13)
C12—N1—C1—C2	−0.9 (2)	C16—C17—C18—C19	74.85 (14)
Mn1—N2—C10—C9	174.67 (12)	O5—C18—C19—C14	36.49 (13)
Mn1—N2—C11—C7	−176.57 (11)	O5—C18—C19—C20	−81.13 (13)
Mn1—N2—C11—C12	3.80 (16)	O5—C18—C19—C21	159.74 (11)
C10—N2—C11—C7	−1.2 (2)	C17—C18—C19—C14	−71.88 (13)
C10—N2—C11—C12	179.19 (13)	C17—C18—C19—C20	170.50 (11)
C11—N2—C10—C9	−0.3 (2)	C17—C18—C19—C21	51.37 (17)
N1—C1—C2—C3	−0.0 (2)	C14—C19—C20—O3	−90.97 (14)
C1—C2—C3—C4	0.8 (2)	C14—C19—C20—O4	89.64 (14)
C2—C3—C4—C5	−179.65 (17)	C18—C19—C20—O3	18.59 (17)
C2—C3—C4—C12	−0.7 (2)	C18—C19—C20—O4	−160.80 (12)
C3—C4—C5—C6	−179.71 (17)	C21—C19—C20—O3	141.71 (13)
C3—C4—C12—N1	−0.2 (2)	C21—C19—C20—O4	−37.69 (17)
C3—C4—C12—C11	−179.22 (14)

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x, y, −z+1/2; (iii) x, −y, z−1/2; (iv) x, y, z−1; (v) x−1/2, −y+1/2, z−1/2; (vi) x−1/2, y+1/2, z; (vii) −x+1/2, y+1/2, −z+1/2; (viii) x+1/2, y−1/2, z; (ix) x+1/2, −y+1/2, z−1/2; (x) −x+1/2, −y+1/2, −z+2; (xi) x, −y, z+1/2; (xii) x, y, z+1; (xiii) x−1/2, −y+1/2, z+1/2; (xiv) −x, y, −z+3/2; (xv) −x+1/2, y−1/2, −z+1/2; (xvi) −x+1, y, −z+1/2; (xvii) x+1/2, −y+1/2, z+1/2; (xviii) −x, −y, −z+1; (xix) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O(6)—H(601)···O(9)^i	0.91	2.04	2.949 (2)	174
O(7)—H(701)···O(9)^i	0.90	1.91	2.809 (2)	176
O(8)—H(801)···O(2)	0.91	1.84	2.7466 (18)	176
O(8)—H(802)···O(7)^viii	0.92	1.95	2.836 (2)	161
O(9)—H(901)···O(1)	0.91	1.87	2.7710 (17)	178
O(9)—H(902)···O(8)	0.92	1.95	2.772 (2)	147

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