Anisotropic thermal expansion in a metal–organic framework

Madsen, S.R.; Lock, N.; Overgaard, J.; Iversen, B.B.

doi:10.1107/S2052520614003497

Anisotropic thermal expansion in a metal–organic framework

S. R. Madsen, N. Lock, J. Overgaard and B. B. Iversen

Ionothermal reaction between Mn^II(acetate)₂·4H₂O and 1,3,5-benzenetricarboxylic acid (H₃BTC) in either of the two ionic liquids 1-ethyl-3-methylimidazolium bromide (EMIMBr) and 1-ethyl-3-methylimidazolium tosylate (EMIMOTs) resulted in the formation of the new metal–organic framework (MOF) EMIM[Mn^IIBTC] (BTC = 1,3,5-benzenetricarboxylate). The compound crystallizes in the orthorhombic space group Pbca with unit-cell parameters of a = 14.66658 (12), b = 12.39497 (9), c = 16.63509 (14) Å at 100 K. Multi-temperature single-crystal (15–340 K) and powder X-ray diffraction studies (100–400 K) reveal strongly anisotropic thermal expansion properties. The linear thermal expansion coefficients, α_L(l), attain maximum values at 400 K along the a- and b-axis, with α_L(a) = 115 × 10⁻⁶ K⁻¹ and α_L(b) = 75 × 10⁻⁶ K⁻¹. At 400 K a negative thermal expansion coefficient of −40 × 10⁻⁶ K⁻¹ is observed along the c-axis. The thermal expansion is coupled to a continuous deformation of the framework, which causes the structure to expand in two directions. Due to the rigidity of the linker, the expansion in the ab plane causes the network to contract along the c-axis. Hirshfeld surface analysis has been used to describe the interaction between the framework structure and the EMIM cation that resides within the channel. This reveals a number of rather weak interactions and one governing hydrogen-bonding interactions.

Keywords: metal–organic framework; thermal expansion; multi-temperature X-ray diffraction.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614003497/gw5029sup1.cif Contains datablocks A100k, A200k, A293k, c100k, c160k, c220k, c280k, c300k, c320k, c340k
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614003497/gw5029a100ksup2.hkl Contains datablock a100k
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614003497/gw5029c100ksup3.hkl Contains datablock c100k
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614003497/gw5029c220ksup4.hkl Contains datablock c220k
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614003497/gw5029c280ksup5.hkl Contains datablock c280k
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614003497/gw5029c300ksup6.hkl Contains datablock c300k
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614003497/gw5029c320ksup7.hkl Contains datablock c320k
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614003497/gw5029c340ksup8.hkl Contains datablock c340k
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614003497/gw5029c160ksup9.hkl Contains datablock c160k
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614003497/gw5029sup10.pdf Additional information

Computing details top

Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) for A100k, A200k, A293k; CrysAlis PRO, Agilent Technologies, Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET) (compiled Mar 7 2011,18:06:32) for c100k, c160k, c220k, c280k, c300k, c320k, c340k. Cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) for A100k, A200k, A293k; CrysAlis PRO, Agilent Technologies, Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET) (compiled Mar 7 2011,18:06:32) for c100k, c160k, c220k, c280k, c300k, c320k, c340k. Data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) for A100k, A200k, A293k; CrysAlis PRO, Agilent Technologies, Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET) (compiled Mar 7 2011,18:06:32) for c100k, c160k, c220k, c280k, c300k, c320k, c340k. Program(s) used to solve structure: XL, G.M. Sheldrick for A100k; SHELXS97 (Sheldrick, 1990) for A200k, A293k. Program(s) used to refine structure: XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 for A100k; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 for A200k, A293k, c100k, c160k, c220k, c280k, c300k, c320k, c340k. For all compounds, molecular graphics: O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341.; software used to prepare material for publication: O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341.

(A100k) top

Crystal data top

C₉H₃MnO₆·C₆H₁₁N₂	D_x = 1.636 Mg m⁻³
M_r = 373.22	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, Pbca	Cell parameters from 19221 reflections
a = 14.66658 (13) Å	θ = 1.6–26.3°
b = 12.39497 (9) Å	µ = 0.91 mm⁻¹
c = 16.63509 (14) Å	T = 100 K
V = 3024.12 (4) Å³	Prismatic, colorless
Z = 8	0.15 × 0.1 × 0.1 mm
F(000) = 1528

Data collection top

SuperNova, Single source at offset), Atlas diffractometer	3085 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2595 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.052
Detector resolution: 10.3590 pixels mm^-1	θ_max = 26.4°, θ_min = 2.5°
ω scans	h = −18→18
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −15→15
T_min = 0.944, T_max = 1.000	l = −20→20
62926 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0298P)² + 3.1301P] where P = (F_o² + 2F_c²)/3
3085 reflections	(Δ/σ)_max = 0.001
252 parameters	Δρ_max = 0.48 e Å⁻³
308 restraints	Δρ_min = −0.29 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mn1	0.60521 (2)	0.48211 (2)	0.57858 (2)	0.01431 (9)
O5	0.70905 (11)	0.47937 (11)	0.48412 (9)	0.0285 (3)
O6	0.69872 (10)	0.63114 (11)	0.55141 (8)	0.0244 (3)
O3	0.59455 (10)	0.34596 (11)	0.66585 (8)	0.0230 (3)
O2	0.49860 (9)	0.57987 (10)	0.62631 (8)	0.0183 (3)
C6	0.34762 (13)	0.78092 (14)	0.54026 (11)	0.0165 (4)
H6	0.3437	0.7546	0.4880	0.020*
C12	0.3436 (4)	0.2375 (4)	0.7759 (3)	0.0373 (11)	0.833 (4)
H12	0.3236	0.1670	0.7834	0.045*	0.833 (4)
C10	0.3921 (2)	0.2204 (3)	0.6314 (2)	0.0479 (9)	0.833 (4)
H10A	0.4254	0.1553	0.6419	0.072*	0.833 (4)
H10B	0.4255	0.2642	0.5940	0.072*	0.833 (4)
H10C	0.3337	0.2028	0.6089	0.072*	0.833 (4)
C13	0.3426 (2)	0.3163 (3)	0.8314 (2)	0.0388 (8)	0.833 (4)
H13	0.3225	0.3103	0.8842	0.047*	0.833 (4)
C14	0.3886 (2)	0.5147 (2)	0.8322 (2)	0.0449 (9)	0.833 (4)
H14A	0.3292	0.5468	0.8417	0.054*	0.833 (4)
H14B	0.4222	0.5616	0.7961	0.054*	0.833 (4)
C10A	0.3434 (14)	0.3807 (17)	0.8949 (10)	0.064 (6)*	0.167 (4)
H10D	0.3975	0.3727	0.9269	0.096*	0.167 (4)
H10E	0.2977	0.3312	0.9134	0.096*	0.167 (4)
H10F	0.3210	0.4532	0.8998	0.096*	0.167 (4)
C15A	0.462 (2)	0.137 (3)	0.623 (2)	0.167 (17)*	0.167 (4)
H15D	0.4856	0.1009	0.6703	0.251*	0.167 (4)
H15E	0.5024	0.1950	0.6091	0.251*	0.167 (4)
H15F	0.4583	0.0867	0.5797	0.251*	0.167 (4)
N1	0.3794 (6)	0.2794 (4)	0.7058 (3)	0.0375 (14)	0.833 (4)
N2A	0.374 (4)	0.267 (2)	0.7045 (15)	0.033 (7)*	0.167 (4)
O1	0.52326 (9)	0.38012 (10)	0.50253 (7)	0.0188 (3)
C9	0.73158 (13)	0.57672 (15)	0.49526 (11)	0.0182 (4)
C4	0.69562 (12)	0.41130 (15)	0.85950 (11)	0.0165 (4)
H4	0.7266	0.4739	0.8452	0.020*
C8	0.63727 (13)	0.39929 (15)	0.71807 (11)	0.0173 (4)
C5	0.70287 (13)	0.37141 (15)	0.93758 (11)	0.0165 (4)
C7	0.46284 (12)	0.63615 (14)	0.57134 (11)	0.0153 (4)
O4	0.67486 (10)	0.48798 (11)	0.70128 (8)	0.0219 (3)
C12A	0.3942 (11)	0.4246 (12)	0.7521 (11)	0.025 (4)*	0.167 (4)
H12A	0.4070	0.4976	0.7583	0.030*	0.167 (4)
C15	0.4395 (2)	0.5047 (3)	0.9112 (2)	0.0568 (10)	0.833 (4)
H15A	0.4998	0.4779	0.9012	0.085*	0.833 (4)
H15B	0.4076	0.4557	0.9459	0.085*	0.833 (4)
H15C	0.4432	0.5743	0.9364	0.085*	0.833 (4)
N2	0.37718 (16)	0.4083 (2)	0.7948 (2)	0.0351 (7)	0.833 (4)
N1A	0.3646 (10)	0.3582 (13)	0.8110 (8)	0.027 (3)*	0.167 (4)
C14A	0.3696 (17)	0.1812 (19)	0.6413 (15)	0.066 (8)*	0.167 (4)
H14C	0.3302	0.1233	0.6595	0.079*	0.167 (4)
H14D	0.3436	0.2111	0.5926	0.079*	0.167 (4)
C11	0.39740 (19)	0.3835 (3)	0.7201 (3)	0.0340 (7)	0.833 (4)
H11	0.4209	0.4315	0.6825	0.041*	0.833 (4)
C11A	0.357 (2)	0.2568 (18)	0.7844 (14)	0.035 (7)*	0.167 (4)
H11A	0.3440	0.1946	0.8134	0.042*	0.167 (4)
C13A	0.4023 (11)	0.3689 (12)	0.6829 (9)	0.025 (4)*	0.167 (4)
H13A	0.4220	0.3933	0.6330	0.029*	0.167 (4)
C2	0.59313 (12)	0.26701 (15)	0.82532 (11)	0.0162 (4)
H2	0.5580	0.2308	0.7874	0.019*
C1	0.40392 (12)	0.72966 (14)	0.59571 (11)	0.0155 (4)
C3	0.64237 (13)	0.35806 (14)	0.80271 (11)	0.0155 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.01763 (16)	0.01430 (15)	0.01099 (15)	0.00055 (11)	0.00109 (11)	0.00051 (11)
O5	0.0358 (9)	0.0224 (7)	0.0272 (8)	−0.0123 (6)	0.0118 (7)	−0.0056 (6)
O6	0.0305 (8)	0.0218 (7)	0.0208 (7)	−0.0031 (6)	0.0100 (6)	0.0004 (6)
O3	0.0335 (8)	0.0221 (7)	0.0133 (7)	−0.0035 (6)	−0.0051 (6)	0.0026 (5)
O2	0.0221 (7)	0.0172 (6)	0.0155 (6)	0.0040 (5)	−0.0015 (5)	−0.0002 (5)
C6	0.0209 (9)	0.0162 (9)	0.0124 (9)	−0.0007 (7)	−0.0003 (8)	−0.0011 (7)
C12	0.021 (2)	0.0309 (19)	0.060 (3)	0.0016 (16)	−0.0059 (17)	0.0224 (16)
C10	0.0309 (18)	0.051 (2)	0.062 (2)	0.0013 (17)	0.0015 (16)	0.0152 (17)
C13	0.0216 (14)	0.0342 (16)	0.060 (2)	−0.0019 (13)	0.0030 (13)	0.0267 (16)
C14	0.0272 (15)	0.0356 (15)	0.072 (2)	−0.0013 (12)	0.0072 (15)	0.0101 (15)
N1	0.021 (2)	0.0309 (19)	0.061 (2)	0.0021 (16)	−0.0012 (12)	0.0219 (13)
O1	0.0230 (7)	0.0195 (7)	0.0138 (6)	0.0002 (6)	0.0010 (5)	−0.0019 (5)
C9	0.0182 (10)	0.0209 (9)	0.0155 (9)	−0.0011 (8)	−0.0009 (7)	0.0020 (8)
C4	0.0152 (9)	0.0162 (9)	0.0180 (9)	−0.0001 (7)	0.0007 (7)	0.0015 (7)
C8	0.0157 (9)	0.0198 (9)	0.0163 (9)	0.0026 (7)	−0.0002 (7)	0.0027 (7)
C5	0.0165 (9)	0.0170 (9)	0.0160 (9)	0.0004 (7)	−0.0014 (7)	−0.0019 (7)
C7	0.0146 (9)	0.0152 (9)	0.0163 (9)	−0.0032 (7)	−0.0020 (7)	−0.0009 (7)
O4	0.0249 (8)	0.0214 (7)	0.0193 (7)	−0.0044 (6)	−0.0030 (6)	0.0071 (6)
C15	0.0364 (18)	0.067 (2)	0.067 (2)	0.0065 (17)	0.0132 (17)	−0.0141 (19)
N2	0.0195 (12)	0.0320 (14)	0.0538 (19)	−0.0003 (10)	0.0071 (11)	0.0209 (12)
C11	0.0166 (14)	0.0336 (17)	0.052 (2)	0.0026 (12)	0.0020 (15)	0.0186 (17)
C2	0.0165 (9)	0.0169 (9)	0.0152 (9)	0.0009 (7)	−0.0019 (7)	−0.0010 (7)
C1	0.0171 (9)	0.0137 (9)	0.0156 (9)	−0.0011 (7)	−0.0008 (7)	−0.0008 (7)
C3	0.0156 (9)	0.0165 (9)	0.0144 (9)	0.0024 (7)	−0.0002 (7)	0.0018 (7)

Geometric parameters (Å, º) top

Mn1—O5	2.1885 (15)	N1—C11	1.339 (6)
Mn1—O6	2.3447 (14)	N2A—C14A	1.497 (18)
Mn1—O3	2.2316 (14)	N2A—C11A	1.358 (19)
Mn1—O2	2.1316 (13)	N2A—C13A	1.376 (18)
Mn1—O1	2.1547 (13)	O1—C7ⁱⁱ	1.262 (2)
Mn1—C9	2.5946 (19)	C9—C5ⁱⁱⁱ	1.503 (3)
Mn1—C8	2.5806 (18)	C4—C5	1.394 (3)
Mn1—O4	2.2837 (14)	C4—C3	1.392 (3)
O5—C9	1.265 (2)	C8—O4	1.261 (2)
O6—C9	1.249 (2)	C8—C3	1.500 (2)
O3—C8	1.259 (2)	C5—C6^iv	1.394 (3)
O2—C7	1.264 (2)	C5—C9^v	1.503 (3)
C6—C5ⁱ	1.394 (3)	C7—O1ⁱⁱ	1.262 (2)
C6—C1	1.392 (3)	C7—C1	1.501 (3)
C12—C13	1.344 (6)	C12A—N1A	1.352 (15)
C12—N1	1.380 (5)	C12A—C13A	1.347 (12)
C10—N1	1.450 (6)	N2—C11	1.315 (5)
C13—N2	1.389 (4)	N1A—C11A	1.338 (18)
C14—C15	1.515 (5)	C2—C1^iv	1.394 (2)
C14—N2	1.468 (4)	C2—C3	1.392 (3)
C10A—N1A	1.457 (16)	C1—C2ⁱ	1.394 (2)
C15A—C14A	1.494 (19)

O5—Mn1—O6	57.78 (5)	C13A—N2A—C14A	118.9 (19)
O5—Mn1—O3	120.28 (6)	C7ⁱⁱ—O1—Mn1	125.12 (12)
O5—Mn1—C9	29.11 (6)	O5—C9—Mn1	57.34 (10)
O5—Mn1—C8	120.84 (6)	O5—C9—C5ⁱⁱⁱ	118.80 (17)
O5—Mn1—O4	109.33 (6)	O6—C9—Mn1	64.46 (10)
O6—Mn1—C9	28.73 (5)	O6—C9—O5	121.60 (18)
O6—Mn1—C8	112.34 (6)	O6—C9—C5ⁱⁱⁱ	119.56 (17)
O3—Mn1—O6	139.65 (5)	C5ⁱⁱⁱ—C9—Mn1	172.51 (13)
O3—Mn1—C9	137.68 (6)	C3—C4—C5	120.47 (17)
O3—Mn1—C8	29.19 (5)	O3—C8—Mn1	59.84 (9)
O3—Mn1—O4	58.26 (5)	O3—C8—O4	121.50 (17)
O2—Mn1—O5	141.88 (5)	O3—C8—C3	119.59 (17)
O2—Mn1—O6	93.04 (5)	O4—C8—Mn1	62.21 (10)
O2—Mn1—O3	97.82 (5)	O4—C8—C3	118.90 (17)
O2—Mn1—O1	98.22 (5)	C3—C8—Mn1	171.43 (13)
O2—Mn1—C9	117.78 (6)	C6^iv—C5—C9^v	121.02 (16)
O2—Mn1—C8	91.42 (5)	C6^iv—C5—C4	119.44 (17)
O2—Mn1—O4	88.68 (5)	C4—C5—C9^v	119.48 (17)
O1—Mn1—O5	87.57 (5)	O2—C7—C1	118.00 (16)
O1—Mn1—O6	132.48 (5)	O1ⁱⁱ—C7—O2	123.32 (17)
O1—Mn1—O3	84.22 (5)	O1ⁱⁱ—C7—C1	118.64 (16)
O1—Mn1—C9	110.49 (5)	C8—O4—Mn1	88.55 (11)
O1—Mn1—C8	113.34 (6)	C13A—C12A—N1A	109.7 (13)
O1—Mn1—O4	142.46 (5)	C13—N2—C14	126.5 (3)
C8—Mn1—C9	122.00 (6)	C11—N2—C13	107.7 (3)
O4—Mn1—O6	83.42 (5)	C11—N2—C14	125.8 (3)
O4—Mn1—C9	98.25 (5)	C12A—N1A—C10A	130.3 (16)
O4—Mn1—C8	29.24 (5)	C11A—N1A—C10A	118.7 (19)
C9—O5—Mn1	93.55 (12)	C11A—N1A—C12A	110.9 (15)
C9—O6—Mn1	86.81 (11)	C15A—C14A—N2A	111 (3)
C8—O3—Mn1	90.97 (11)	N2—C11—N1	110.4 (3)
C7—O2—Mn1	110.40 (11)	N1A—C11A—N2A	102.8 (18)
C1—C6—C5ⁱ	120.49 (17)	C12A—C13A—N2A	102.8 (15)
C13—C12—N1	108.1 (5)	C3—C2—C1^iv	120.54 (17)
C12—C13—N2	107.0 (3)	C6—C1—C7	121.00 (16)
N2—C14—C15	110.5 (3)	C6—C1—C2ⁱ	119.44 (17)
C12—N1—C10	125.5 (5)	C2ⁱ—C1—C7	119.55 (16)
C11—N1—C12	106.7 (5)	C4—C3—C8	120.24 (17)
C11—N1—C10	127.7 (4)	C2—C3—C4	119.47 (17)
C11A—N2A—C14A	128 (2)	C2—C3—C8	120.29 (17)
C11A—N2A—C13A	113.3 (18)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, −y+1, z−1/2; (iv) −x+1, y−1/2, −z+3/2; (v) −x+3/2, −y+1, z+1/2.

(A200k) top

Crystal data top

C₉H₃MnO₆·C₆H₁₁N₂	D_x = 1.621 Mg m⁻³
M_r = 373.22	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, Pbca	Cell parameters from 16059 reflections
a = 14.77158 (16) Å	θ = 1.6–27.8°
b = 12.42598 (11) Å	µ = 0.90 mm⁻¹
c = 16.62769 (16) Å	T = 200 K
V = 3052.03 (5) Å³	Prismatic, colorless
Z = 8	0.15 × 0.1 × 0.1 mm
F(000) = 1528

Data collection top

SuperNova, Single source at offset), Atlas diffractometer	3642 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2904 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.056
Detector resolution: 10.3590 pixels mm^-1	θ_max = 27.9°, θ_min = 2.5°
ω scans	h = −19→19
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −16→16
T_min = 0.961, T_max = 1.000	l = −21→21
65078 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0208P)² + 2.6647P] where P = (F_o² + 2F_c²)/3
3642 reflections	(Δ/σ)_max = 0.001
252 parameters	Δρ_max = 0.31 e Å⁻³
310 restraints	Δρ_min = −0.35 e Å⁻³

Special details top

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mn1	0.60476 (2)	0.48355 (2)	0.57927 (2)	0.01867 (8)
O5	0.70911 (11)	0.48089 (11)	0.48541 (9)	0.0403 (4)
O6	0.69819 (11)	0.63237 (11)	0.55128 (8)	0.0359 (4)
O3	0.59329 (10)	0.34818 (11)	0.66732 (8)	0.0310 (3)
O2	0.49845 (9)	0.58148 (10)	0.62566 (7)	0.0246 (3)
C6	0.34726 (12)	0.78084 (14)	0.53932 (11)	0.0217 (4)
H6	0.3430	0.7542	0.4872	0.026*
C12	0.3434 (4)	0.2387 (4)	0.7748 (3)	0.0555 (12)	0.867 (4)
H12	0.3243	0.1682	0.7827	0.067*	0.867 (4)
C10	0.3918 (3)	0.2209 (4)	0.6302 (3)	0.0713 (11)	0.867 (4)
H10A	0.4276	0.1579	0.6409	0.107*	0.867 (4)
H10B	0.4227	0.2656	0.5919	0.107*	0.867 (4)
H10C	0.3342	0.1997	0.6087	0.107*	0.867 (4)
C13	0.3420 (2)	0.3179 (3)	0.8300 (2)	0.0554 (10)	0.867 (4)
H13	0.3219	0.3123	0.8829	0.066*	0.867 (4)
C14	0.3879 (2)	0.5157 (3)	0.8298 (3)	0.0680 (11)	0.867 (4)
H14A	0.3291	0.5480	0.8394	0.082*	0.867 (4)
H14B	0.4212	0.5621	0.7934	0.082*	0.867 (4)
C10A	0.347 (3)	0.383 (3)	0.8991 (15)	0.134 (14)*	0.133 (4)
H10D	0.4023	0.3747	0.9291	0.202*	0.133 (4)
H10E	0.3026	0.3336	0.9185	0.202*	0.133 (4)
H10F	0.3252	0.4556	0.9056	0.202*	0.133 (4)
C15A	0.461 (3)	0.147 (5)	0.628 (3)	0.23 (3)*	0.133 (4)
H15D	0.4829	0.1118	0.6753	0.351*	0.133 (4)
H15E	0.5002	0.2061	0.6145	0.351*	0.133 (4)
H15F	0.4596	0.0969	0.5840	0.351*	0.133 (4)
N1	0.3782 (5)	0.2804 (4)	0.7044 (3)	0.0525 (14)	0.867 (4)
N2A	0.374 (4)	0.270 (2)	0.7090 (16)	0.043 (8)*	0.133 (4)
O1	0.52509 (9)	0.38039 (10)	0.50320 (7)	0.0246 (3)
C9	0.73148 (13)	0.57772 (15)	0.49609 (11)	0.0244 (4)
C4	0.69506 (12)	0.41174 (14)	0.86066 (10)	0.0213 (4)
H4	0.7256	0.4744	0.8466	0.026*
C8	0.63627 (12)	0.40077 (14)	0.71923 (11)	0.0219 (4)
C5	0.70289 (12)	0.37115 (14)	0.93850 (10)	0.0211 (4)
C7	0.46217 (12)	0.63685 (13)	0.57053 (10)	0.0193 (4)
O4	0.67367 (10)	0.48897 (11)	0.70250 (8)	0.0303 (3)
C12A	0.3917 (19)	0.4265 (17)	0.7518 (13)	0.050 (6)*	0.133 (4)
H12A	0.4033	0.4998	0.7564	0.060*	0.133 (4)
C15	0.4390 (3)	0.5060 (4)	0.9090 (3)	0.0893 (14)	0.867 (4)
H15A	0.4987	0.4786	0.8989	0.134*	0.867 (4)
H15B	0.4072	0.4578	0.9441	0.134*	0.867 (4)
H15C	0.4433	0.5756	0.9338	0.134*	0.867 (4)
N2	0.37619 (16)	0.4095 (2)	0.7932 (2)	0.0501 (7)	0.867 (4)
N1A	0.3648 (14)	0.3625 (17)	0.8132 (11)	0.044 (5)*	0.133 (4)
C14A	0.367 (3)	0.189 (3)	0.643 (2)	0.101 (15)*	0.133 (4)
H14C	0.3426	0.2224	0.5949	0.121*	0.133 (4)
H14D	0.3268	0.1307	0.6587	0.121*	0.133 (4)
C11	0.3967 (2)	0.3838 (3)	0.7191 (3)	0.0477 (8)	0.867 (4)
H11	0.4210	0.4312	0.6816	0.057*	0.867 (4)
C11A	0.354 (3)	0.261 (2)	0.7874 (15)	0.035 (7)*	0.133 (4)
H11A	0.3364	0.2009	0.8165	0.042*	0.133 (4)
C13A	0.3993 (16)	0.3695 (16)	0.6831 (11)	0.034 (5)*	0.133 (4)
H13A	0.4171	0.3919	0.6322	0.040*	0.133 (4)
C2	0.59283 (12)	0.26833 (14)	0.82635 (10)	0.0207 (4)
H2	0.5575	0.2326	0.7885	0.025*
C1	0.40377 (12)	0.73029 (14)	0.59484 (10)	0.0196 (4)
C3	0.64164 (12)	0.35903 (14)	0.80374 (10)	0.0195 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.02312 (14)	0.01875 (13)	0.01415 (13)	0.00047 (11)	0.00189 (11)	0.00097 (10)
O5	0.0509 (10)	0.0312 (7)	0.0389 (9)	−0.0196 (7)	0.0186 (7)	−0.0071 (7)
O6	0.0470 (9)	0.0314 (7)	0.0293 (7)	−0.0055 (7)	0.0187 (7)	−0.0006 (6)
O3	0.0432 (9)	0.0326 (7)	0.0171 (6)	−0.0063 (6)	−0.0073 (6)	0.0045 (6)
O2	0.0289 (7)	0.0234 (6)	0.0214 (7)	0.0076 (5)	−0.0023 (5)	−0.0006 (5)
C6	0.0269 (10)	0.0218 (8)	0.0165 (9)	0.0008 (7)	−0.0021 (7)	−0.0014 (7)
C12	0.035 (2)	0.044 (2)	0.088 (3)	−0.0001 (19)	−0.006 (2)	0.0335 (19)
C10	0.050 (2)	0.065 (2)	0.099 (3)	0.009 (2)	0.006 (2)	0.019 (2)
C13	0.0340 (16)	0.0499 (18)	0.082 (2)	−0.0039 (14)	0.0050 (15)	0.0376 (19)
C14	0.0406 (18)	0.0503 (17)	0.113 (3)	−0.0021 (14)	0.0153 (18)	0.0087 (18)
N1	0.0288 (18)	0.0419 (18)	0.087 (3)	0.0046 (13)	0.0019 (13)	0.0307 (14)
O1	0.0305 (7)	0.0255 (7)	0.0178 (6)	−0.0003 (6)	0.0024 (5)	−0.0044 (5)
C9	0.0260 (10)	0.0273 (9)	0.0199 (9)	−0.0036 (8)	0.0008 (7)	0.0037 (7)
C4	0.0214 (9)	0.0202 (8)	0.0224 (9)	−0.0021 (7)	0.0006 (7)	0.0025 (7)
C8	0.0214 (9)	0.0243 (9)	0.0200 (9)	0.0025 (7)	−0.0002 (7)	0.0047 (7)
C5	0.0210 (9)	0.0231 (9)	0.0193 (9)	−0.0014 (7)	−0.0023 (7)	−0.0017 (7)
C7	0.0199 (8)	0.0179 (8)	0.0203 (9)	−0.0016 (7)	−0.0017 (7)	−0.0024 (7)
O4	0.0362 (8)	0.0287 (7)	0.0260 (7)	−0.0068 (6)	−0.0047 (6)	0.0109 (6)
C15	0.059 (2)	0.105 (3)	0.104 (3)	0.009 (2)	0.020 (2)	−0.027 (3)
N2	0.0279 (13)	0.0461 (14)	0.076 (2)	−0.0003 (11)	0.0089 (12)	0.0284 (14)
C11	0.0248 (14)	0.0420 (17)	0.076 (3)	0.0050 (13)	0.0037 (19)	0.0288 (18)
C2	0.0225 (9)	0.0219 (9)	0.0176 (8)	−0.0011 (7)	−0.0028 (7)	−0.0009 (7)
C1	0.0215 (9)	0.0184 (8)	0.0190 (8)	0.0011 (7)	−0.0006 (7)	−0.0012 (6)
C3	0.0207 (9)	0.0207 (8)	0.0172 (8)	0.0011 (7)	−0.0009 (7)	0.0022 (7)

Geometric parameters (Å, º) top

Mn1—O5	2.1939 (15)	N1—C11	1.336 (6)
Mn1—O6	2.3540 (14)	N2A—C14A	1.489 (19)
Mn1—O3	2.2364 (13)	N2A—C11A	1.340 (19)
Mn1—O2	2.1311 (13)	N2A—C13A	1.367 (19)
Mn1—O1	2.1512 (13)	O1—C7ⁱⁱ	1.259 (2)
Mn1—C9	2.6051 (19)	C9—C5ⁱⁱⁱ	1.503 (2)
Mn1—C8	2.5866 (18)	C4—C5	1.394 (2)
Mn1—O4	2.2889 (13)	C4—C3	1.396 (2)
O5—C9	1.260 (2)	C8—O4	1.258 (2)
O6—C9	1.243 (2)	C8—C3	1.500 (2)
O3—C8	1.255 (2)	C5—C6^iv	1.394 (2)
O2—C7	1.265 (2)	C5—C9^v	1.503 (2)
C6—C5ⁱ	1.394 (2)	C7—O1ⁱⁱ	1.259 (2)
C6—C1	1.394 (2)	C7—C1	1.502 (2)
C12—C13	1.347 (6)	C12A—N1A	1.354 (17)
C12—N1	1.380 (5)	C12A—C13A	1.349 (13)
C10—N1	1.453 (6)	N2—C11	1.309 (5)
C13—N2	1.387 (4)	N1A—C11A	1.337 (18)
C14—C15	1.522 (5)	C2—C1^iv	1.394 (2)
C14—N2	1.464 (4)	C2—C3	1.390 (2)
C10A—N1A	1.474 (18)	C1—C2ⁱ	1.394 (2)
C15A—C14A	1.51 (2)

O5—Mn1—O6	57.26 (5)	C13A—N2A—C14A	113 (2)
O5—Mn1—O3	120.50 (6)	C7ⁱⁱ—O1—Mn1	126.33 (12)
O5—Mn1—C9	28.86 (5)	O5—C9—Mn1	57.16 (10)
O5—Mn1—C8	120.50 (6)	O5—C9—C5ⁱⁱⁱ	118.86 (17)
O5—Mn1—O4	108.95 (6)	O6—C9—Mn1	64.48 (10)
O6—Mn1—C9	28.46 (5)	O6—C9—O5	121.46 (17)
O6—Mn1—C8	112.63 (6)	O6—C9—C5ⁱⁱⁱ	119.63 (17)
O3—Mn1—O6	139.88 (5)	C5ⁱⁱⁱ—C9—Mn1	172.44 (13)
O3—Mn1—C9	137.72 (6)	C5—C4—C3	120.45 (16)
O3—Mn1—C8	29.02 (5)	O3—C8—Mn1	59.82 (9)
O3—Mn1—O4	57.98 (5)	O3—C8—O4	121.56 (17)
O2—Mn1—O5	141.61 (6)	O3—C8—C3	119.40 (16)
O2—Mn1—O6	93.15 (5)	O4—C8—Mn1	62.21 (9)
O2—Mn1—O3	97.86 (5)	O4—C8—C3	119.02 (16)
O2—Mn1—O1	98.63 (5)	C3—C8—Mn1	171.84 (13)
O2—Mn1—C9	117.72 (6)	C6^iv—C5—C9^v	120.95 (16)
O2—Mn1—C8	91.95 (5)	C4—C5—C6^iv	119.52 (16)
O2—Mn1—O4	89.25 (5)	C4—C5—C9^v	119.47 (16)
O1—Mn1—O5	87.54 (5)	O2—C7—C1	117.95 (15)
O1—Mn1—O6	132.27 (5)	O1ⁱⁱ—C7—O2	123.35 (16)
O1—Mn1—O3	83.99 (5)	O1ⁱⁱ—C7—C1	118.66 (15)
O1—Mn1—C9	110.40 (5)	C8—O4—Mn1	88.69 (11)
O1—Mn1—C8	112.99 (5)	C13A—C12A—N1A	110.8 (18)
O1—Mn1—O4	141.92 (5)	C13—N2—C14	126.8 (4)
C8—Mn1—C9	121.80 (6)	C11—N2—C13	107.4 (3)
O4—Mn1—O6	83.86 (5)	C11—N2—C14	125.8 (3)
O4—Mn1—C9	98.19 (5)	C12A—N1A—C10A	133 (2)
O4—Mn1—C8	29.10 (5)	C11A—N1A—C10A	117 (3)
C9—O5—Mn1	93.99 (12)	C11A—N1A—C12A	110.2 (18)
C9—O6—Mn1	87.06 (11)	N2A—C14A—C15A	107 (4)
C8—O3—Mn1	91.16 (11)	N2—C11—N1	111.1 (3)
C7—O2—Mn1	111.13 (11)	N1A—C11A—N2A	102 (2)
C1—C6—C5ⁱ	120.37 (16)	C12A—C13A—N2A	100.7 (19)
C13—C12—N1	108.1 (4)	C3—C2—C1^iv	120.71 (16)
C12—C13—N2	107.0 (3)	C6—C1—C7	120.93 (15)
N2—C14—C15	110.3 (3)	C2ⁱ—C1—C6	119.43 (16)
C12—N1—C10	125.5 (4)	C2ⁱ—C1—C7	119.63 (16)
C11—N1—C12	106.4 (5)	C4—C3—C8	120.19 (16)
C11—N1—C10	128.1 (5)	C2—C3—C4	119.37 (16)
C11A—N2A—C14A	131 (3)	C2—C3—C8	120.44 (16)
C11A—N2A—C13A	116 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, −y+1, z−1/2; (iv) −x+1, y−1/2, −z+3/2; (v) −x+3/2, −y+1, z+1/2.

(A293k) top

Crystal data top

C₉H₃MnO₆·C₆H₁₁N₂	D_x = 1.6 Mg m⁻³
M_r = 373.22	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, Pbca	Cell parameters from 18118 reflections
a = 14.92869 (16) Å	θ = 1.6–27.0°
b = 12.49901 (11) Å	µ = 0.89 mm⁻¹
c = 16.58142 (15) Å	T = 293 K
V = 3093.99 (5) Å³	Prismatic, colorless
Z = 8	0.15 × 0.1 × 0.1 mm
F(000) = 1528

Data collection top

SuperNova, Single source at offset), Atlas diffractometer	3410 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2721 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.059
Detector resolution: 10.3590 pixels mm^-1	θ_max = 27.1°, θ_min = 2.5°
ω scans	h = −19→19
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −16→16
T_min = 0.961, T_max = 1.000	l = −21→21
83298 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0296P)² + 2.6174P] where P = (F_o² + 2F_c²)/3
3410 reflections	(Δ/σ)_max = 0.001
252 parameters	Δρ_max = 0.44 e Å⁻³
308 restraints	Δρ_min = −0.33 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mn1	0.60410 (2)	0.48591 (2)	0.58143 (2)	0.02605 (10)
O5	0.70823 (14)	0.48420 (14)	0.48821 (12)	0.0592 (5)
O6	0.69846 (13)	0.63408 (14)	0.55358 (11)	0.0544 (5)
O3	0.59201 (12)	0.35245 (13)	0.67052 (9)	0.0456 (4)
O2	0.49855 (10)	0.58519 (12)	0.62365 (9)	0.0354 (4)
C6	0.34702 (14)	0.78080 (16)	0.53671 (12)	0.0305 (5)
H6	0.3424	0.7535	0.4847	0.037*
C12	0.3428 (4)	0.2416 (5)	0.7722 (4)	0.0802 (17)	0.873 (5)
H12	0.3249	0.1714	0.7813	0.096*	0.873 (5)
C10	0.3904 (4)	0.2203 (5)	0.6267 (4)	0.1069 (18)	0.873 (5)
H10A	0.4328	0.1641	0.6369	0.160*	0.873 (5)
H10B	0.4133	0.2667	0.5854	0.160*	0.873 (5)
H10C	0.3347	0.1897	0.6092	0.160*	0.873 (5)
C13	0.3408 (3)	0.3208 (4)	0.8264 (3)	0.0828 (15)	0.873 (5)
H13	0.3210	0.3161	0.8794	0.099*	0.873 (5)
C14	0.3846 (3)	0.5189 (4)	0.8221 (4)	0.120 (2)	0.873 (5)
H14A	0.3262	0.5502	0.8319	0.144*	0.873 (5)
H14B	0.4165	0.5643	0.7843	0.144*	0.873 (5)
C10A	0.347 (3)	0.390 (4)	0.8942 (17)	0.155 (19)*	0.127 (5)
H10D	0.4021	0.3807	0.9237	0.233*	0.127 (5)
H10E	0.3025	0.3425	0.9156	0.233*	0.127 (5)
H10F	0.3272	0.4624	0.8991	0.233*	0.127 (5)
C15A	0.467 (4)	0.148 (7)	0.640 (5)	0.30 (4)*	0.127 (5)
H15D	0.4765	0.1223	0.5864	0.456*	0.127 (5)
H15E	0.4758	0.0913	0.6780	0.456*	0.127 (5)
H15F	0.5076	0.2055	0.6514	0.456*	0.127 (5)
N1	0.3760 (5)	0.2814 (4)	0.7003 (4)	0.0801 (17)	0.873 (5)
N2A	0.379 (3)	0.273 (2)	0.7110 (14)	0.035 (6)*	0.127 (5)
O1	0.52765 (11)	0.38079 (12)	0.50551 (8)	0.0351 (4)
C9	0.73146 (15)	0.57952 (18)	0.49881 (13)	0.0353 (5)
C4	0.69402 (14)	0.41214 (16)	0.86382 (12)	0.0296 (4)
H4	0.7245	0.4744	0.8498	0.036*
C8	0.63408 (14)	0.40394 (17)	0.72266 (13)	0.0309 (4)
C5	0.70263 (14)	0.37062 (17)	0.94150 (12)	0.0299 (4)
C7	0.46131 (13)	0.63850 (15)	0.56818 (12)	0.0266 (4)
O4	0.67059 (12)	0.49162 (13)	0.70615 (10)	0.0453 (4)
C12A	0.391 (2)	0.429 (2)	0.7490 (16)	0.064 (8)*	0.127 (5)
H12A	0.4021	0.5024	0.7537	0.077*	0.127 (5)
C15	0.4373 (4)	0.5117 (6)	0.9019 (5)	0.172 (3)	0.873 (5)
H15A	0.4971	0.4872	0.8912	0.258*	0.873 (5)
H15B	0.4080	0.4623	0.9375	0.258*	0.873 (5)
H15C	0.4396	0.5810	0.9267	0.258*	0.873 (5)
N2	0.3742 (2)	0.4115 (3)	0.7880 (3)	0.0781 (11)	0.873 (5)
N1A	0.3623 (18)	0.365 (2)	0.8105 (13)	0.055 (6)*	0.127 (5)
C14A	0.372 (4)	0.189 (3)	0.647 (3)	0.116 (19)*	0.127 (5)
H14C	0.3508	0.2194	0.5969	0.139*	0.127 (5)
H14D	0.3310	0.1325	0.6638	0.139*	0.127 (5)
C11	0.3941 (3)	0.3837 (4)	0.7147 (4)	0.0733 (12)	0.873 (5)
H11	0.4184	0.4300	0.6766	0.088*	0.873 (5)
C11A	0.354 (3)	0.264 (2)	0.7873 (15)	0.038 (7)*	0.127 (5)
H11A	0.3363	0.2037	0.8163	0.045*	0.127 (5)
C13A	0.401 (2)	0.3718 (19)	0.6803 (13)	0.046 (7)*	0.127 (5)
H13A	0.4175	0.3927	0.6286	0.056*	0.127 (5)
C2	0.59214 (14)	0.27078 (16)	0.82931 (12)	0.0285 (4)
H2	0.5566	0.2361	0.7914	0.034*
C1	0.40353 (13)	0.73162 (16)	0.59233 (12)	0.0270 (4)
C3	0.64023 (14)	0.36115 (16)	0.80707 (12)	0.0276 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.03163 (18)	0.02672 (16)	0.01979 (16)	0.00084 (13)	0.00259 (13)	0.00153 (12)
O5	0.0742 (13)	0.0476 (10)	0.0559 (11)	−0.0292 (9)	0.0273 (10)	−0.0097 (9)
O6	0.0705 (13)	0.0472 (10)	0.0454 (10)	−0.0081 (9)	0.0316 (9)	−0.0006 (8)
O3	0.0647 (12)	0.0468 (9)	0.0252 (8)	−0.0114 (8)	−0.0123 (8)	0.0090 (7)
O2	0.0419 (9)	0.0343 (8)	0.0299 (8)	0.0122 (7)	−0.0029 (7)	−0.0006 (6)
C6	0.0382 (12)	0.0301 (10)	0.0232 (10)	0.0038 (9)	−0.0052 (9)	−0.0039 (8)
C12	0.051 (3)	0.063 (3)	0.126 (4)	−0.002 (2)	−0.008 (3)	0.049 (2)
C10	0.086 (4)	0.088 (3)	0.147 (5)	0.012 (3)	0.014 (3)	0.032 (3)
C13	0.055 (2)	0.073 (3)	0.120 (4)	−0.006 (2)	0.005 (2)	0.048 (3)
C14	0.074 (3)	0.076 (3)	0.209 (6)	−0.013 (2)	0.035 (3)	0.000 (3)
N1	0.049 (2)	0.063 (2)	0.128 (4)	0.0103 (16)	0.003 (2)	0.049 (2)
O1	0.0440 (9)	0.0361 (8)	0.0252 (8)	0.0001 (7)	0.0025 (7)	−0.0065 (6)
C9	0.0363 (12)	0.0395 (12)	0.0300 (11)	−0.0044 (10)	0.0049 (9)	0.0045 (9)
C4	0.0304 (11)	0.0287 (10)	0.0299 (11)	−0.0038 (9)	−0.0010 (9)	0.0026 (8)
C8	0.0296 (11)	0.0352 (11)	0.0279 (10)	0.0021 (9)	−0.0012 (8)	0.0073 (9)
C5	0.0306 (11)	0.0326 (11)	0.0264 (10)	−0.0027 (9)	−0.0054 (8)	−0.0001 (8)
C7	0.0264 (10)	0.0257 (9)	0.0278 (11)	−0.0013 (8)	−0.0021 (8)	−0.0030 (8)
O4	0.0570 (11)	0.0417 (9)	0.0371 (9)	−0.0117 (8)	−0.0082 (8)	0.0164 (7)
C15	0.090 (4)	0.193 (7)	0.233 (7)	0.019 (4)	0.024 (4)	−0.087 (6)
N2	0.0422 (18)	0.068 (2)	0.124 (3)	−0.0029 (15)	0.0175 (19)	0.040 (2)
C11	0.0338 (18)	0.061 (2)	0.125 (4)	0.0085 (18)	0.013 (3)	0.045 (2)
C2	0.0319 (11)	0.0293 (10)	0.0243 (10)	−0.0026 (8)	−0.0052 (8)	0.0006 (8)
C1	0.0306 (10)	0.0261 (10)	0.0242 (10)	0.0014 (8)	−0.0018 (8)	−0.0006 (8)
C3	0.0293 (10)	0.0300 (10)	0.0236 (10)	0.0014 (8)	−0.0019 (8)	0.0034 (8)

Geometric parameters (Å, º) top

Mn1—O5	2.1923 (18)	N1—C11	1.328 (7)
Mn1—O6	2.3723 (17)	N2A—C14A	1.49 (2)
Mn1—O3	2.2355 (16)	N2A—C11A	1.324 (19)
Mn1—O2	2.1243 (15)	N2A—C13A	1.378 (19)
Mn1—O1	2.1479 (15)	O1—C7ⁱⁱ	1.256 (2)
Mn1—C9	2.619 (2)	C9—C5ⁱⁱⁱ	1.503 (3)
Mn1—C8	2.595 (2)	C4—C5	1.395 (3)
Mn1—O4	2.2951 (17)	C4—C3	1.392 (3)
O5—C9	1.253 (3)	C8—O4	1.254 (3)
O6—C9	1.238 (3)	C8—C3	1.501 (3)
O3—C8	1.247 (3)	C5—C6^iv	1.393 (3)
O2—C7	1.265 (2)	C5—C9^v	1.503 (3)
C6—C5ⁱ	1.393 (3)	C7—O1ⁱⁱ	1.256 (2)
C6—C1	1.393 (3)	C7—C1	1.503 (3)
C12—C13	1.337 (8)	C12A—N1A	1.366 (18)
C12—N1	1.382 (6)	C12A—C13A	1.356 (18)
C10—N1	1.457 (7)	N2—C11	1.299 (7)
C13—N2	1.392 (5)	N1A—C11A	1.331 (19)
C14—C15	1.542 (9)	C2—C1^iv	1.390 (3)
C14—N2	1.465 (6)	C2—C3	1.388 (3)
C10A—N1A	1.439 (19)	C1—C2ⁱ	1.390 (3)
C15A—C14A	1.51 (5)

O5—Mn1—O6	56.58 (6)	C13A—N2A—C14A	113 (3)
O5—Mn1—O3	121.06 (7)	C7ⁱⁱ—O1—Mn1	128.16 (14)
O5—Mn1—C9	28.46 (7)	O5—C9—Mn1	56.48 (12)
O5—Mn1—C8	120.67 (8)	O5—C9—C5ⁱⁱⁱ	119.1 (2)
O5—Mn1—O4	109.21 (8)	O6—C9—Mn1	64.75 (12)
O6—Mn1—C9	28.16 (6)	O6—C9—O5	121.1 (2)
O6—Mn1—C8	112.42 (7)	O6—C9—C5ⁱⁱⁱ	119.7 (2)
O3—Mn1—O6	139.39 (7)	C5ⁱⁱⁱ—C9—Mn1	172.29 (16)
O3—Mn1—C9	137.52 (7)	C3—C4—C5	120.48 (19)
O3—Mn1—C8	28.72 (6)	O3—C8—Mn1	59.43 (11)
O3—Mn1—O4	57.50 (6)	O3—C8—O4	121.2 (2)
O2—Mn1—O5	139.81 (7)	O3—C8—C3	119.54 (19)
O2—Mn1—O6	92.78 (6)	O4—C8—Mn1	62.16 (11)
O2—Mn1—O3	99.10 (6)	O4—C8—C3	119.23 (19)
O2—Mn1—O1	98.99 (6)	C3—C8—Mn1	173.03 (15)
O2—Mn1—C9	116.73 (7)	C6^iv—C5—C9^v	121.23 (19)
O2—Mn1—C8	93.51 (6)	C6^iv—C5—C4	119.37 (19)
O2—Mn1—O4	90.33 (6)	C4—C5—C9^v	119.34 (19)
O1—Mn1—O5	87.57 (6)	O2—C7—C1	117.81 (17)
O1—Mn1—O6	132.76 (6)	O1ⁱⁱ—C7—O2	123.27 (19)
O1—Mn1—O3	83.57 (6)	O1ⁱⁱ—C7—C1	118.89 (18)
O1—Mn1—C9	110.63 (6)	C8—O4—Mn1	88.94 (13)
O1—Mn1—C8	112.28 (6)	C13A—C12A—N1A	110 (2)
O1—Mn1—O4	140.99 (6)	C13—N2—C14	127.4 (5)
C8—Mn1—C9	121.54 (7)	C11—N2—C13	107.0 (4)
O4—Mn1—O6	83.93 (6)	C11—N2—C14	125.6 (5)
O4—Mn1—C9	98.25 (7)	C12A—N1A—C10A	130 (3)
O4—Mn1—C8	28.90 (6)	C11A—N1A—C10A	118 (3)
C9—O5—Mn1	95.05 (14)	C11A—N1A—C12A	112 (2)
C9—O6—Mn1	87.08 (14)	N2A—C14A—C15A	103 (5)
C8—O3—Mn1	91.85 (13)	N2—C11—N1	112.2 (5)
C7—O2—Mn1	113.22 (13)	N2A—C11A—N1A	100 (2)
C1—C6—C5ⁱ	120.41 (19)	C12A—C13A—N2A	98.2 (19)
C13—C12—N1	108.7 (5)	C3—C2—C1^iv	120.72 (19)
C12—C13—N2	106.7 (5)	C6—C1—C7	120.85 (18)
N2—C14—C15	109.4 (5)	C2ⁱ—C1—C6	119.46 (18)
C12—N1—C10	125.9 (6)	C2ⁱ—C1—C7	119.67 (18)
C11—N1—C12	105.4 (6)	C4—C3—C8	120.16 (18)
C11—N1—C10	128.7 (6)	C2—C3—C4	119.43 (18)
C11A—N2A—C14A	126 (3)	C2—C3—C8	120.40 (18)
C11A—N2A—C13A	120 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, −y+1, z−1/2; (iv) −x+1, y−1/2, −z+3/2; (v) −x+3/2, −y+1, z+1/2.

(c100k) top

Crystal data top

C₉H₃MnO₆·C₆H₁₁N₂	D_x = 1.643 Mg m⁻³
M_r = 373.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2242 reflections
a = 14.6452 (4) Å	θ = 2.4–29.3°
b = 12.3672 (4) Å	µ = 0.91 mm⁻¹
c = 16.6648 (5) Å	T = 100 K
V = 3018.33 (16) Å³	Prism, colorless
Z = 8	0.15 × 0.11 × 0.07 mm
F(000) = 1528

Data collection top

SuperNova, Single source at offset), Atlas diffractometer	3611 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2412 reflections with I > 2σ(I)
Detector resolution: 10.3590 pixels mm^-1	R_int = 0.061
ω scans	θ_max = 29.3°, θ_min = 2.4°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET) (compiled Mar 7 2011,18:06:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→18
T_min = 0.977, T_max = 1.000	k = −16→12
10796 measured reflections	l = −19→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0362P)² + 0.987P] where P = (F_o² + 2F_c²)/3
3611 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.57 e Å⁻³
308 restraints	Δρ_min = −0.57 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O4	0.67534 (15)	0.48793 (17)	0.70085 (13)	0.0211 (5)
O5	0.70950 (15)	0.47909 (18)	0.48389 (14)	0.0249 (6)
O3	0.59521 (15)	0.34538 (17)	0.66611 (13)	0.0237 (5)
O6	0.69875 (15)	0.63023 (17)	0.55109 (13)	0.0239 (5)
C9	0.7314 (2)	0.5737 (3)	0.49452 (18)	0.0158 (6)
C8	0.63842 (19)	0.3976 (2)	0.71656 (18)	0.0145 (6)
C3	0.6427 (2)	0.3582 (2)	0.80239 (18)	0.0160 (7)
O2	0.49864 (14)	0.57963 (16)	0.62623 (12)	0.0169 (5)
N1A	0.370 (4)	0.268 (3)	0.701 (2)	0.041 (11)*	0.179 (6)
C11	0.3976 (3)	0.3836 (5)	0.7212 (4)	0.0303 (11)	0.821 (6)
H11	0.4214	0.4322	0.6823	0.036*	0.821 (6)
C10	0.3927 (5)	0.2209 (6)	0.6330 (4)	0.0450 (15)	0.821 (6)
H10D	0.3333	0.1969	0.6126	0.067*	0.821 (6)
H10E	0.4316	0.1579	0.6427	0.067*	0.821 (6)
H10F	0.4218	0.2682	0.5934	0.067*	0.821 (6)
C12	0.3436 (7)	0.2363 (7)	0.7774 (5)	0.0379 (18)	0.821 (6)
H12	0.3231	0.1642	0.7851	0.046*	0.821 (6)
C13	0.3433 (3)	0.3161 (4)	0.8317 (3)	0.0378 (13)	0.821 (6)
H13	0.3230	0.3102	0.8857	0.045*	0.821 (6)
C14	0.3891 (3)	0.5158 (4)	0.8330 (3)	0.0416 (13)	0.821 (6)
H14C	0.3283	0.5480	0.8431	0.050*	0.821 (6)
H14D	0.4228	0.5644	0.7963	0.050*	0.821 (6)
C15	0.4400 (4)	0.5063 (5)	0.9105 (3)	0.0529 (16)	0.821 (6)
H15D	0.4995	0.4726	0.9007	0.079*	0.821 (6)
H15E	0.4049	0.4616	0.9480	0.079*	0.821 (6)
H15F	0.4489	0.5784	0.9335	0.079*	0.821 (6)
Mn1	0.60517 (3)	0.48140 (4)	0.57834 (3)	0.01355 (15)
C7	0.4630 (2)	0.6366 (2)	0.57131 (18)	0.0141 (6)
C6	0.3478 (2)	0.7816 (2)	0.54075 (18)	0.0169 (7)
H6	0.3442	0.7554	0.4873	0.020*
C1	0.4037 (2)	0.7297 (2)	0.59605 (18)	0.0149 (7)
C5	0.7030 (2)	0.3719 (2)	0.93676 (18)	0.0161 (7)
C2	0.5933 (2)	0.2670 (2)	0.82546 (18)	0.0155 (7)
H2	0.5571	0.2299	0.7870	0.019*
C4	0.6959 (2)	0.4119 (2)	0.85911 (18)	0.0169 (7)
H4	0.7274	0.4761	0.8446	0.020*
O1	0.52298 (14)	0.37976 (16)	0.50259 (12)	0.0171 (5)
N2A	0.3647 (15)	0.3603 (19)	0.8094 (11)	0.031 (6)*	0.179 (6)
C12A	0.4020 (18)	0.3697 (18)	0.6809 (14)	0.033 (6)*	0.179 (6)
H12A	0.4223	0.3943	0.6299	0.039*	0.179 (6)
C13A	0.3978 (19)	0.4266 (19)	0.7499 (15)	0.034 (7)*	0.179 (6)
H13A	0.4148	0.5002	0.7564	0.041*	0.179 (6)
C14A	0.3395 (19)	0.378 (3)	0.8925 (13)	0.071 (9)*	0.179 (6)
H14A	0.3060	0.3142	0.9124	0.085*	0.179 (6)
H14B	0.2973	0.4409	0.8951	0.085*	0.179 (6)
C15A	0.418 (3)	0.399 (4)	0.946 (2)	0.15 (2)*	0.179 (6)
H15A	0.4742	0.3714	0.9215	0.231*	0.179 (6)
H15B	0.4082	0.3632	0.9978	0.231*	0.179 (6)
H15C	0.4245	0.4774	0.9550	0.231*	0.179 (6)
N1	0.3798 (7)	0.2800 (6)	0.7077 (5)	0.0335 (17)	0.821 (6)
N2	0.3780 (3)	0.4101 (4)	0.7954 (3)	0.0330 (11)	0.821 (6)
C10A	0.374 (3)	0.185 (3)	0.637 (3)	0.089 (19)*	0.179 (6)
H10A	0.3587	0.2185	0.5852	0.133*	0.179 (6)
H10B	0.3303	0.1278	0.6490	0.133*	0.179 (6)
H10C	0.4358	0.1549	0.6342	0.133*	0.179 (6)
C11A	0.354 (3)	0.260 (2)	0.7805 (19)	0.033 (10)*	0.179 (6)
H11A	0.3392	0.1963	0.8098	0.040*	0.179 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0243 (12)	0.0215 (12)	0.0176 (11)	−0.0047 (10)	−0.0031 (10)	0.0057 (9)
O5	0.0307 (13)	0.0214 (12)	0.0226 (12)	−0.0060 (10)	0.0113 (11)	−0.0027 (10)
O3	0.0365 (14)	0.0188 (12)	0.0158 (11)	−0.0045 (10)	−0.0016 (11)	0.0026 (9)
O6	0.0294 (13)	0.0228 (13)	0.0194 (12)	−0.0049 (10)	0.0096 (11)	−0.0010 (10)
C9	0.0119 (15)	0.0257 (17)	0.0099 (14)	0.0027 (12)	−0.0031 (12)	0.0023 (13)
C8	0.0095 (15)	0.0161 (16)	0.0180 (15)	0.0006 (12)	0.0000 (13)	0.0075 (12)
C3	0.0153 (16)	0.0164 (16)	0.0163 (14)	0.0012 (12)	0.0004 (13)	0.0010 (12)
O2	0.0198 (11)	0.0153 (11)	0.0157 (11)	0.0034 (9)	−0.0020 (9)	0.0006 (9)
C11	0.014 (2)	0.032 (3)	0.045 (3)	0.0007 (19)	−0.001 (2)	0.020 (2)
C10	0.030 (3)	0.047 (4)	0.058 (3)	0.004 (3)	−0.004 (3)	0.013 (3)
C12	0.023 (3)	0.029 (3)	0.062 (4)	0.004 (3)	0.000 (2)	0.025 (2)
C13	0.027 (3)	0.033 (3)	0.054 (3)	−0.001 (2)	0.001 (2)	0.029 (2)
C14	0.024 (3)	0.034 (3)	0.066 (3)	−0.0013 (19)	0.007 (2)	0.007 (2)
C15	0.038 (3)	0.061 (4)	0.060 (3)	0.004 (3)	0.012 (3)	−0.007 (3)
Mn1	0.0164 (3)	0.0129 (3)	0.0113 (2)	0.00004 (19)	0.0006 (2)	0.00046 (19)
C7	0.0116 (15)	0.0151 (16)	0.0157 (15)	−0.0036 (11)	−0.0022 (13)	−0.0012 (13)
C6	0.0189 (16)	0.0177 (17)	0.0140 (15)	−0.0011 (13)	0.0000 (14)	−0.0004 (13)
C1	0.0153 (16)	0.0141 (16)	0.0154 (15)	0.0014 (12)	−0.0028 (13)	−0.0013 (12)
C5	0.0149 (16)	0.0182 (17)	0.0152 (15)	−0.0009 (13)	−0.0002 (13)	−0.0025 (13)
C2	0.0168 (16)	0.0165 (16)	0.0133 (15)	0.0002 (12)	−0.0020 (14)	−0.0028 (13)
C4	0.0166 (16)	0.0145 (16)	0.0196 (15)	−0.0001 (12)	0.0002 (13)	0.0015 (13)
O1	0.0193 (12)	0.0171 (12)	0.0149 (11)	0.0010 (9)	0.0003 (10)	−0.0015 (9)
N1	0.016 (3)	0.031 (3)	0.054 (3)	0.002 (2)	−0.006 (2)	0.0183 (19)
N2	0.018 (2)	0.028 (2)	0.052 (3)	−0.0014 (16)	0.0054 (18)	0.0208 (18)

Geometric parameters (Å, º) top

O4—C8	1.269 (3)	C12—C13	1.339 (9)
O4—Mn1	2.287 (2)	C12—N1	1.386 (7)
O5—C9	1.226 (4)	C13—N2	1.406 (6)
O5—Mn1	2.194 (2)	C14—C15	1.495 (7)
O3—C8	1.234 (4)	C14—N2	1.459 (6)
O3—Mn1	2.234 (2)	Mn1—O1	2.150 (2)
O6—C9	1.267 (4)	C7—C1	1.500 (4)
O6—Mn1	2.339 (2)	C7—O1ⁱⁱ	1.265 (3)
C9—Mn1	2.583 (3)	C6—C1	1.390 (4)
C9—C5ⁱ	1.517 (4)	C6—C5ⁱⁱⁱ	1.393 (4)
C8—C3	1.512 (4)	C1—C2ⁱⁱⁱ	1.388 (4)
C8—Mn1	2.572 (3)	C5—C9^iv	1.517 (4)
C3—C2	1.394 (4)	C5—C6^v	1.393 (4)
C3—C4	1.393 (4)	C5—C4	1.389 (4)
O2—Mn1	2.132 (2)	C2—C1^v	1.388 (4)
O2—C7	1.267 (3)	O1—C7ⁱⁱ	1.264 (3)
N1A—C12A	1.378 (19)	N2A—C13A	1.374 (18)
N1A—C10A	1.47 (2)	N2A—C14A	1.451 (18)
N1A—C11A	1.36 (2)	N2A—C11A	1.342 (19)
C11—N1	1.327 (9)	C12A—C13A	1.350 (13)
C11—N2	1.310 (7)	C14A—C15A	1.485 (19)
C10—N1	1.456 (8)

C8—O4—Mn1	87.80 (18)	C8—Mn1—C9	121.79 (9)
C9—O5—Mn1	93.80 (19)	O2—Mn1—O4	88.54 (8)
C8—O3—Mn1	91.08 (18)	O2—Mn1—O5	141.77 (8)
C9—O6—Mn1	86.08 (18)	O2—Mn1—O3	97.82 (8)
O5—C9—O6	122.3 (3)	O2—Mn1—O6	93.04 (8)
O5—C9—Mn1	57.93 (16)	O2—Mn1—C9	118.32 (9)
O5—C9—C5ⁱ	119.8 (3)	O2—Mn1—C8	91.89 (9)
O6—C9—Mn1	64.61 (16)	O2—Mn1—O1	98.23 (8)
O6—C9—C5ⁱ	117.8 (3)	O1—Mn1—O4	142.78 (8)
C5ⁱ—C9—Mn1	172.8 (2)	O1—Mn1—O5	87.77 (8)
O4—C8—C3	117.4 (3)	O1—Mn1—O3	84.70 (8)
O4—C8—Mn1	62.67 (15)	O1—Mn1—O6	132.38 (8)
O3—C8—O4	122.6 (3)	O1—Mn1—C9	109.98 (9)
O3—C8—C3	119.8 (3)	O1—Mn1—C8	113.33 (9)
O3—C8—Mn1	60.26 (16)	O2—C7—C1	117.8 (3)
C3—C8—Mn1	169.9 (2)	O1ⁱⁱ—C7—O2	123.2 (3)
C2—C3—C8	120.0 (3)	O1ⁱⁱ—C7—C1	118.9 (3)
C4—C3—C8	120.8 (3)	C1—C6—C5ⁱⁱⁱ	120.4 (3)
C4—C3—C2	119.2 (3)	C6—C1—C7	120.9 (3)
C7—O2—Mn1	110.32 (18)	C2ⁱⁱⁱ—C1—C7	119.7 (3)
C12A—N1A—C10A	117 (3)	C2ⁱⁱⁱ—C1—C6	119.3 (3)
C11A—N1A—C12A	111 (3)	C6^v—C5—C9^iv	121.5 (3)
C11A—N1A—C10A	131 (3)	C4—C5—C9^iv	118.7 (3)
N2—C11—N1	111.0 (5)	C4—C5—C6^v	119.7 (3)
C13—C12—N1	106.3 (7)	C1^v—C2—C3	120.8 (3)
C12—C13—N2	108.5 (6)	C5—C4—C3	120.3 (3)
N2—C14—C15	110.9 (4)	C7ⁱⁱ—O1—Mn1	125.05 (19)
O4—Mn1—O6	83.24 (8)	C13A—N2A—C14A	133 (2)
O4—Mn1—C9	98.36 (9)	C11A—N2A—C13A	110 (2)
O4—Mn1—C8	29.53 (8)	C11A—N2A—C14A	117 (3)
O5—Mn1—O4	109.15 (9)	C13A—C12A—N1A	105 (2)
O5—Mn1—O3	120.36 (9)	C12A—C13A—N2A	109 (2)
O5—Mn1—O6	57.52 (8)	N2A—C14A—C15A	114 (3)
O5—Mn1—C9	28.27 (9)	C11—N1—C10	127.2 (6)
O5—Mn1—C8	120.36 (9)	C11—N1—C12	108.0 (7)
O3—Mn1—O4	58.09 (8)	C12—N1—C10	124.8 (7)
O3—Mn1—O6	139.27 (8)	C11—N2—C13	106.2 (5)
O3—Mn1—C9	137.19 (9)	C11—N2—C14	127.2 (5)
O3—Mn1—C8	28.67 (8)	C13—N2—C14	126.6 (5)
O6—Mn1—C9	29.31 (8)	N2A—C11A—N1A	105 (2)
O6—Mn1—C8	112.34 (9)

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+3/2, −y+1, z+1/2; (v) −x+1, y−1/2, −z+3/2.

(c160k) top

Crystal data top

C₉H₃MnO₆·C₆H₁₁N₂	D_x = 1.634 Mg m⁻³
M_r = 373.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2092 reflections
a = 14.7079 (5) Å	θ = 2.4–29.3°
b = 12.3931 (4) Å	µ = 0.91 mm⁻¹
c = 16.6458 (5) Å	T = 160 K
V = 3034.14 (17) Å³	Prism, colorless
Z = 8	0.15 × 0.11 × 0.07 mm
F(000) = 1528

Data collection top

SuperNova, Single source at offset), Atlas diffractometer	3632 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2276 reflections with I > 2σ(I)
Detector resolution: 10.3590 pixels mm^-1	R_int = 0.064
ω scans	θ_max = 29.3°, θ_min = 2.5°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET) (compiled Mar 7 2011,18:06:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→18
T_min = 0.974, T_max = 1.000	k = −12→16
10847 measured reflections	l = −22→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0525P)² + 6.2464P] where P = (F_o² + 2F_c²)/3
3632 reflections	(Δ/σ)_max = 0.002
212 parameters	Δρ_max = 0.88 e Å⁻³
282 restraints	Δρ_min = −0.61 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O2	0.49859 (19)	0.5806 (2)	0.62602 (17)	0.0218 (6)
O3	0.5952 (2)	0.3468 (2)	0.66660 (18)	0.0299 (7)
O1	0.52422 (19)	0.3799 (2)	0.50315 (16)	0.0214 (6)
O4	0.6741 (2)	0.4887 (2)	0.70191 (17)	0.0265 (7)
C7	0.4624 (3)	0.6371 (3)	0.5709 (2)	0.0176 (8)
C2	0.5932 (3)	0.2675 (3)	0.8258 (2)	0.0199 (9)
H2	0.5576	0.2305	0.7870	0.024*
C9	0.7313 (3)	0.5746 (4)	0.4951 (2)	0.0209 (9)
C10	0.3911 (7)	0.2212 (8)	0.6321 (5)	0.057 (2)*	0.797 (7)
H10A	0.4357	0.1636	0.6408	0.086*	0.797 (7)
H10B	0.4128	0.2694	0.5896	0.086*	0.797 (7)
H10C	0.3328	0.1894	0.6162	0.086*	0.797 (7)
C11A	0.3485 (15)	0.2618 (18)	0.7903 (12)	0.014 (4)*	0.203 (7)
H11A	0.3242	0.2034	0.8205	0.016*	0.203 (7)
C12A	0.4002 (13)	0.3676 (14)	0.6852 (12)	0.015 (4)*	0.203 (7)
H12A	0.4187	0.3940	0.6341	0.018*	0.203 (7)
C13A	0.3936 (17)	0.4206 (17)	0.7537 (13)	0.030 (5)*	0.203 (7)
H13A	0.4066	0.4954	0.7587	0.036*	0.203 (7)
C14	0.3884 (5)	0.5157 (6)	0.8324 (5)	0.053 (2)*	0.797 (7)
H14A	0.3280	0.5480	0.8427	0.063*	0.797 (7)
H14B	0.4218	0.5639	0.7953	0.063*	0.797 (7)
C15	0.4387 (6)	0.5073 (7)	0.9084 (5)	0.068 (3)*	0.797 (7)
H15A	0.4985	0.4751	0.8983	0.102*	0.797 (7)
H15B	0.4046	0.4617	0.9459	0.102*	0.797 (7)
H15C	0.4465	0.5794	0.9316	0.102*	0.797 (7)
O5	0.7093 (2)	0.4809 (2)	0.48469 (19)	0.0337 (8)
C6	0.3472 (3)	0.7812 (3)	0.5403 (2)	0.0196 (9)
H6	0.3428	0.7541	0.4870	0.023*
C5	0.7030 (3)	0.3715 (3)	0.9376 (2)	0.0208 (9)
C4	0.6954 (3)	0.4113 (3)	0.8599 (2)	0.0206 (9)
H4	0.7271	0.4752	0.8454	0.025*
C1	0.4036 (3)	0.7302 (3)	0.5953 (2)	0.0185 (8)
C3	0.6424 (3)	0.3592 (3)	0.8034 (2)	0.0202 (9)
C8	0.6377 (3)	0.3984 (3)	0.7175 (2)	0.0195 (8)
N1A	0.374 (3)	0.2631 (18)	0.7062 (15)	0.048 (6)*	0.203 (7)
C12	0.3451 (6)	0.2363 (7)	0.7739 (5)	0.044 (2)*	0.797 (7)
H12	0.3261	0.1636	0.7809	0.053*	0.797 (7)
C13	0.3434 (5)	0.3171 (6)	0.8310 (4)	0.0432 (18)*	0.797 (7)
H13	0.3232	0.3103	0.8849	0.052*	0.797 (7)
C14A	0.345 (2)	0.381 (3)	0.8978 (15)	0.095 (12)*	0.203 (7)
H14C	0.3168	0.3149	0.9208	0.114*	0.203 (7)
H14D	0.2988	0.4387	0.8996	0.114*	0.203 (7)
C15A	0.424 (3)	0.413 (5)	0.951 (2)	0.146 (19)*	0.203 (7)
H15D	0.4807	0.3850	0.9279	0.219*	0.203 (7)
H15E	0.4153	0.3833	1.0047	0.219*	0.203 (7)
H15F	0.4272	0.4919	0.9539	0.219*	0.203 (7)
N1	0.3794 (7)	0.2817 (6)	0.7054 (4)	0.0418 (18)*	0.797 (7)
C10A	0.381 (5)	0.184 (4)	0.641 (3)	0.14 (2)*	0.203 (7)
H10D	0.4455	0.1649	0.6338	0.208*	0.203 (7)
H10E	0.3571	0.2144	0.5917	0.208*	0.203 (7)
H10F	0.3469	0.1188	0.6557	0.208*	0.203 (7)
C11	0.3966 (5)	0.3849 (6)	0.7216 (5)	0.0388 (16)*	0.797 (7)
H11	0.4207	0.4343	0.6836	0.047*	0.797 (7)
N2	0.3768 (4)	0.4102 (5)	0.7950 (4)	0.0402 (15)*	0.797 (7)
N2A	0.367 (2)	0.360 (2)	0.8152 (12)	0.065 (6)*	0.203 (7)
O6	0.6983 (2)	0.6313 (2)	0.55136 (18)	0.0321 (8)
Mn1	0.60497 (4)	0.48245 (5)	0.57893 (4)	0.0171 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0258 (15)	0.0208 (15)	0.0187 (14)	0.0047 (12)	−0.0009 (12)	0.0014 (12)
O3	0.043 (2)	0.0257 (16)	0.0213 (15)	−0.0052 (14)	−0.0035 (14)	0.0065 (13)
O1	0.0267 (16)	0.0199 (15)	0.0175 (14)	−0.0012 (12)	0.0007 (13)	−0.0035 (12)
O4	0.0296 (16)	0.0288 (17)	0.0210 (14)	−0.0058 (13)	−0.0033 (13)	0.0085 (12)
C7	0.0178 (19)	0.017 (2)	0.0183 (19)	−0.0022 (15)	−0.0007 (17)	−0.0026 (16)
C2	0.022 (2)	0.020 (2)	0.0182 (19)	0.0000 (16)	−0.0027 (18)	−0.0020 (16)
C9	0.018 (2)	0.029 (2)	0.0157 (18)	−0.0011 (16)	0.0013 (16)	0.0045 (16)
O5	0.0411 (19)	0.0280 (17)	0.0319 (17)	−0.0119 (15)	0.0170 (15)	−0.0033 (14)
C6	0.020 (2)	0.020 (2)	0.019 (2)	−0.0002 (16)	0.0003 (17)	−0.0017 (17)
C5	0.020 (2)	0.023 (2)	0.0195 (19)	0.0001 (17)	−0.0016 (17)	−0.0028 (16)
C4	0.021 (2)	0.018 (2)	0.0226 (19)	−0.0019 (16)	0.0004 (17)	0.0000 (16)
C1	0.018 (2)	0.017 (2)	0.021 (2)	−0.0015 (15)	−0.0008 (17)	−0.0009 (16)
C3	0.023 (2)	0.019 (2)	0.0189 (18)	−0.0002 (16)	−0.0019 (16)	0.0030 (15)
C8	0.0139 (19)	0.023 (2)	0.0219 (18)	−0.0002 (15)	−0.0027 (16)	0.0081 (15)
O6	0.0404 (19)	0.0306 (17)	0.0253 (16)	−0.0058 (14)	0.0150 (15)	−0.0007 (13)
Mn1	0.0210 (3)	0.0166 (3)	0.0138 (3)	0.0003 (2)	0.0013 (3)	0.0004 (2)

Geometric parameters (Å, º) top

O2—C7	1.271 (5)	C14—C15	1.468 (11)
O2—Mn1	2.131 (3)	C14—N2	1.458 (9)
O3—C8	1.231 (5)	O5—Mn1	2.194 (3)
O3—Mn1	2.231 (3)	C6—C5^iv	1.390 (6)
O1—C7ⁱ	1.265 (5)	C6—C1	1.388 (6)
O1—Mn1	2.149 (3)	C5—C9^v	1.516 (6)
O4—C8	1.267 (5)	C5—C6ⁱⁱ	1.390 (6)
O4—Mn1	2.287 (3)	C5—C4	1.389 (6)
C7—O1ⁱ	1.265 (5)	C4—C3	1.383 (6)
C7—C1	1.498 (5)	C1—C2^iv	1.394 (5)
C2—C1ⁱⁱ	1.394 (5)	C3—C8	1.511 (6)
C2—C3	1.397 (6)	C8—Mn1	2.576 (4)
C9—O5	1.218 (5)	N1A—C10A	1.464 (18)
C9—C5ⁱⁱⁱ	1.516 (6)	C12—C13	1.380 (10)
C9—O6	1.268 (5)	C12—N1	1.368 (10)
C9—Mn1	2.589 (4)	C13—N2	1.390 (9)
C10—N1	1.443 (10)	C14A—C15A	1.513 (19)
C11A—N1A	1.448 (18)	C14A—N2A	1.437 (18)
C11A—N2A	1.310 (18)	N1—C11	1.331 (10)
C12A—C13A	1.320 (17)	C11—N2	1.294 (9)
C12A—N1A	1.398 (18)	O6—Mn1	2.344 (3)
C13A—N2A	1.331 (18)

C7—O2—Mn1	110.8 (2)	N2A—C14A—C15A	116 (3)
C8—O3—Mn1	91.5 (2)	C12—N1—C10	122.4 (8)
C7ⁱ—O1—Mn1	125.8 (3)	C11—N1—C10	130.4 (8)
C8—O4—Mn1	88.0 (2)	C11—N1—C12	107.3 (7)
O2—C7—C1	118.0 (3)	N2—C11—N1	112.4 (7)
O1ⁱ—C7—O2	123.2 (4)	C13—N2—C14	127.0 (7)
O1ⁱ—C7—C1	118.8 (4)	C11—N2—C14	126.5 (7)
C1ⁱⁱ—C2—C3	120.3 (4)	C11—N2—C13	106.5 (6)
O5—C9—C5ⁱⁱⁱ	120.0 (4)	C11A—N2A—C13A	110.2 (17)
O5—C9—O6	122.1 (4)	C11A—N2A—C14A	115 (2)
O5—C9—Mn1	57.7 (2)	C13A—N2A—C14A	134 (3)
C5ⁱⁱⁱ—C9—Mn1	173.0 (3)	C9—O6—Mn1	86.1 (2)
O6—C9—C5ⁱⁱⁱ	117.8 (4)	O2—Mn1—O3	98.18 (12)
O6—C9—Mn1	64.6 (2)	O2—Mn1—O1	98.49 (11)
N2A—C11A—N1A	104.0 (17)	O2—Mn1—O4	88.72 (11)
C13A—C12A—N1A	102.9 (16)	O2—Mn1—C9	118.25 (13)
C12A—C13A—N2A	113.8 (17)	O2—Mn1—O5	141.37 (12)
N2—C14—C15	111.3 (7)	O2—Mn1—C8	92.22 (12)
C9—O5—Mn1	94.4 (3)	O2—Mn1—O6	93.01 (11)
C1—C6—C5^iv	120.6 (4)	O3—Mn1—O4	57.89 (11)
C6ⁱⁱ—C5—C9^v	121.8 (4)	O3—Mn1—C9	136.98 (13)
C4—C5—C9^v	118.8 (4)	O3—Mn1—C8	28.54 (12)
C4—C5—C6ⁱⁱ	119.4 (4)	O3—Mn1—O6	139.35 (12)
C3—C4—C5	120.8 (4)	O1—Mn1—O3	84.42 (11)
C2^iv—C1—C7	119.5 (4)	O1—Mn1—O4	142.30 (11)
C6—C1—C7	121.1 (4)	O1—Mn1—C9	109.94 (12)
C6—C1—C2^iv	119.4 (4)	O1—Mn1—O5	87.79 (11)
C2—C3—C8	119.3 (4)	O1—Mn1—C8	112.94 (12)
C4—C3—C2	119.4 (4)	O1—Mn1—O6	132.37 (11)
C4—C3—C8	121.3 (4)	O4—Mn1—C9	98.55 (12)
O3—C8—O4	122.1 (4)	O4—Mn1—C8	29.45 (11)
O3—C8—C3	120.5 (4)	O4—Mn1—O6	83.60 (11)
O3—C8—Mn1	60.0 (2)	O5—Mn1—O3	120.40 (12)
O4—C8—C3	117.3 (4)	O5—Mn1—O4	109.25 (12)
O4—C8—Mn1	62.5 (2)	O5—Mn1—C9	27.98 (12)
C3—C8—Mn1	170.2 (3)	O5—Mn1—C8	120.40 (13)
C11A—N1A—C10A	136 (3)	O5—Mn1—O6	57.17 (11)
C12A—N1A—C11A	108.9 (16)	C8—Mn1—C9	121.79 (13)
C12A—N1A—C10A	115 (2)	O6—Mn1—C9	29.25 (12)
N1—C12—C13	106.3 (7)	O6—Mn1—C8	112.59 (12)
C12—C13—N2	107.5 (7)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+3/2, −y+1, z−1/2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+3/2, −y+1, z+1/2.

(c220k) top

Crystal data top

C₉H₃MnO₆·C₆H₁₁N₂	D_x = 1.622 Mg m⁻³
M_r = 373.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1967 reflections
a = 14.7960 (5) Å	θ = 2.5–29.4°
b = 12.4275 (4) Å	µ = 0.90 mm⁻¹
c = 16.6266 (5) Å	T = 220 K
V = 3057.26 (18) Å³	Prism, colorless
Z = 8	0.15 × 0.11 × 0.07 mm
F(000) = 1528

Data collection top

SuperNova, Single source at offset), Atlas diffractometer	3673 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2208 reflections with I > 2σ(I)
Detector resolution: 10.3590 pixels mm^-1	R_int = 0.066
ω scans	θ_max = 29.5°, θ_min = 2.5°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET) (compiled Mar 7 2011,18:06:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −18→15
T_min = 0.985, T_max = 1.000	k = −16→12
10927 measured reflections	l = −22→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0379P)² + 6.1843P] where P = (F_o² + 2F_c²)/3
3673 reflections	(Δ/σ)_max = 0.001
212 parameters	Δρ_max = 0.91 e Å⁻³
275 restraints	Δρ_min = −0.63 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.52558 (19)	0.3802 (2)	0.50406 (16)	0.0268 (7)
O2	0.49860 (19)	0.5825 (2)	0.62518 (17)	0.0279 (7)
C9	0.7309 (3)	0.5764 (4)	0.4967 (2)	0.0266 (9)
O3	0.5945 (2)	0.3492 (2)	0.66820 (17)	0.0356 (8)
C1	0.4036 (3)	0.7302 (3)	0.5945 (2)	0.0224 (9)
C2	0.5933 (3)	0.2693 (3)	0.8270 (2)	0.0231 (9)
H2	0.5572	0.2331	0.7882	0.028*
C8	0.6369 (3)	0.4005 (3)	0.7191 (2)	0.0233 (9)
C10	0.3934 (8)	0.2204 (10)	0.6360 (7)	0.080 (3)*	0.779 (8)
H10A	0.4410	0.1673	0.6459	0.120*	0.779 (8)
H10B	0.4120	0.2685	0.5923	0.120*	0.779 (8)
H10C	0.3375	0.1833	0.6207	0.120*	0.779 (8)
C11A	0.3463 (16)	0.2276 (16)	0.7534 (12)	0.032 (5)*	0.221 (8)
H11A	0.3238	0.1582	0.7665	0.038*	0.221 (8)
C12A	0.3989 (13)	0.3680 (13)	0.6860 (12)	0.022 (4)*	0.221 (8)
H12A	0.4223	0.4093	0.6427	0.026*	0.221 (8)
C13A	0.3829 (16)	0.4063 (15)	0.7605 (14)	0.030 (4)*	0.221 (8)
H13A	0.3892	0.4779	0.7797	0.035*	0.221 (8)
C14	0.3871 (6)	0.5180 (7)	0.8286 (5)	0.069 (3)*	0.779 (8)
H14A	0.3271	0.5509	0.8381	0.083*	0.779 (8)
H14B	0.4206	0.5638	0.7900	0.083*	0.779 (8)
C15	0.4376 (7)	0.5101 (9)	0.9051 (6)	0.102 (4)*	0.779 (8)
H15A	0.4465	0.5823	0.9275	0.153*	0.779 (8)
H15B	0.4965	0.4766	0.8952	0.153*	0.779 (8)
H15C	0.4033	0.4662	0.9433	0.153*	0.779 (8)
O4	0.6725 (2)	0.4899 (2)	0.70368 (18)	0.0352 (8)
C5	0.7035 (3)	0.3706 (3)	0.9388 (2)	0.0229 (9)
C6	0.3474 (3)	0.7807 (3)	0.5390 (3)	0.0249 (9)
H6	0.3436	0.7538	0.4856	0.030*
C3	0.6418 (3)	0.3601 (3)	0.8042 (2)	0.0232 (9)
C4	0.6951 (3)	0.4115 (3)	0.8611 (2)	0.0248 (9)
H4	0.7262	0.4756	0.8469	0.030*
C7	0.4620 (3)	0.6375 (3)	0.5702 (2)	0.0216 (9)
N1	0.3777 (4)	0.2832 (5)	0.7090 (4)	0.0434 (16)*	0.779 (8)
C12	0.3443 (5)	0.2462 (7)	0.7817 (5)	0.0455 (18)*	0.779 (8)
H12	0.3254	0.1745	0.7920	0.055*	0.779 (8)
C13	0.3426 (7)	0.3232 (7)	0.8329 (6)	0.059 (2)*	0.779 (8)
H13	0.3213	0.3193	0.8867	0.071*	0.779 (8)
C14A	0.347 (3)	0.369 (4)	0.8828 (19)	0.132 (16)*	0.221 (8)
H14C	0.3121	0.3182	0.9168	0.159*	0.221 (8)
H14D	0.3059	0.4303	0.8727	0.159*	0.221 (8)
C15A	0.418 (3)	0.414 (5)	0.938 (3)	0.19 (3)*	0.221 (8)
H15D	0.4333	0.4872	0.9222	0.292*	0.221 (8)
H15E	0.4727	0.3686	0.9353	0.292*	0.221 (8)
H15F	0.3955	0.4137	0.9937	0.292*	0.221 (8)
C10A	0.382 (3)	0.199 (3)	0.6100 (18)	0.068 (11)*	0.221 (8)
H10D	0.4240	0.1388	0.6182	0.102*	0.221 (8)
H10E	0.4045	0.2445	0.5661	0.102*	0.221 (8)
H10F	0.3223	0.1712	0.5962	0.102*	0.221 (8)
C11	0.3962 (5)	0.3878 (6)	0.7220 (6)	0.0480 (18)*	0.779 (8)
H11	0.4197	0.4368	0.6835	0.058*	0.779 (8)
N1A	0.3766 (14)	0.2609 (14)	0.6817 (12)	0.034 (4)*	0.221 (8)
N2	0.3765 (4)	0.4103 (5)	0.7960 (4)	0.0507 (17)*	0.779 (8)
O5	0.7089 (2)	0.4828 (3)	0.4860 (2)	0.0442 (9)
O6	0.6984 (2)	0.6326 (3)	0.55218 (19)	0.0415 (8)
N2A	0.354 (2)	0.3134 (18)	0.8033 (13)	0.064 (6)*	0.221 (8)
Mn1	0.60452 (4)	0.48381 (5)	0.57981 (4)	0.02102 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0329 (17)	0.0274 (16)	0.0202 (14)	−0.0002 (12)	0.0008 (13)	−0.0074 (12)
O2	0.0337 (16)	0.0266 (16)	0.0232 (14)	0.0095 (13)	−0.0030 (13)	−0.0003 (12)
C9	0.027 (2)	0.032 (2)	0.0206 (19)	0.0001 (17)	−0.0005 (18)	0.0025 (17)
O3	0.054 (2)	0.0314 (17)	0.0212 (15)	−0.0088 (15)	−0.0055 (15)	0.0061 (13)
C1	0.024 (2)	0.019 (2)	0.023 (2)	−0.0002 (16)	−0.0017 (18)	−0.0005 (16)
C2	0.027 (2)	0.024 (2)	0.0189 (19)	−0.0015 (16)	−0.0065 (18)	−0.0005 (16)
C8	0.018 (2)	0.027 (2)	0.0250 (18)	0.0007 (16)	−0.0007 (16)	0.0090 (16)
O4	0.0404 (18)	0.0340 (18)	0.0312 (16)	−0.0093 (14)	−0.0063 (15)	0.0116 (14)
C5	0.024 (2)	0.024 (2)	0.0207 (19)	−0.0026 (17)	−0.0023 (17)	−0.0020 (16)
C6	0.030 (2)	0.023 (2)	0.022 (2)	0.0031 (17)	−0.0014 (19)	−0.0044 (17)
C3	0.025 (2)	0.023 (2)	0.0209 (18)	−0.0018 (16)	−0.0018 (16)	0.0029 (16)
C4	0.024 (2)	0.022 (2)	0.028 (2)	−0.0033 (17)	−0.0011 (18)	0.0029 (17)
C7	0.020 (2)	0.021 (2)	0.024 (2)	−0.0021 (15)	−0.0027 (17)	−0.0032 (16)
O5	0.056 (2)	0.0364 (18)	0.0406 (19)	−0.0176 (16)	0.0244 (17)	−0.0046 (15)
O6	0.055 (2)	0.0353 (18)	0.0344 (17)	−0.0084 (16)	0.0218 (17)	−0.0027 (14)
Mn1	0.0262 (4)	0.0198 (3)	0.0171 (3)	0.0005 (3)	0.0017 (3)	0.0007 (3)

Geometric parameters (Å, º) top

O1—C7ⁱ	1.267 (5)	C14—N2	1.453 (10)
O1—Mn1	2.147 (3)	C15—H15A	0.9800
O2—C7	1.263 (5)	C15—H15B	0.9800
O2—Mn1	2.129 (3)	C15—H15C	0.9800
C9—C5ⁱⁱ	1.518 (6)	O4—Mn1	2.293 (3)
C9—O5	1.220 (5)	C5—C9^v	1.518 (6)
C9—O6	1.253 (5)	C5—C6^iv	1.397 (5)
C9—Mn1	2.594 (4)	C5—C4	1.393 (6)
O3—C8	1.231 (5)	C6—C5ⁱⁱⁱ	1.397 (5)
O3—Mn1	2.232 (3)	C6—H6	0.9500
C1—C2ⁱⁱⁱ	1.395 (5)	C3—C4	1.387 (6)
C1—C6	1.391 (6)	C4—H4	0.9500
C1—C7	1.495 (5)	C7—O1ⁱ	1.267 (5)
C2—C1^iv	1.395 (5)	N1—C12	1.384 (9)
C2—H2	0.9500	N1—C11	1.345 (9)
C2—C3	1.390 (5)	C12—H12	0.9500
C8—O4	1.257 (5)	C12—C13	1.281 (11)
C8—C3	1.503 (6)	C13—H13	0.9500
C8—Mn1	2.582 (4)	C13—N2	1.342 (10)
C10—H10A	0.9800	C14A—H14C	0.9900
C10—H10B	0.9800	C14A—H14D	0.9900
C10—H10C	0.9800	C14A—C15A	1.51 (2)
C10—N1	1.463 (12)	C14A—N2A	1.495 (18)
C11A—H11A	0.9500	C15A—H15D	0.9800
C11A—C12A	2.21 (3)	C15A—H15E	0.9800
C11A—N1A	1.339 (17)	C15A—H15F	0.9800
C11A—N2A	1.357 (18)	C10A—H10D	0.9800
C12A—H12A	0.9500	C10A—H10E	0.9800
C12A—C13A	1.347 (17)	C10A—H10F	0.9800
C12A—N1A	1.374 (16)	C10A—N1A	1.42 (3)
C13A—H13A	0.9500	C11—H11	0.9500
C13A—N2A	1.420 (17)	C11—N2	1.295 (10)
C14—H14A	0.9900	O5—Mn1	2.195 (3)
C14—H14B	0.9900	O6—Mn1	2.358 (3)
C14—C15	1.479 (12)

C7ⁱ—O1—Mn1	126.7 (3)	C12—N1—C10	127.2 (7)
C7—O2—Mn1	111.8 (2)	C11—N1—C10	128.1 (8)
C5ⁱⁱ—C9—Mn1	172.6 (3)	C11—N1—C12	104.7 (7)
O5—C9—C5ⁱⁱ	119.5 (4)	N1—C12—H12	125.1
O5—C9—O6	122.4 (4)	C13—C12—N1	109.8 (8)
O5—C9—Mn1	57.5 (2)	C13—C12—H12	125.1
O6—C9—C5ⁱⁱ	118.0 (4)	C12—C13—H13	126.5
O6—C9—Mn1	65.1 (2)	C12—C13—N2	106.9 (8)
C8—O3—Mn1	91.8 (2)	N2—C13—H13	126.5
C2ⁱⁱⁱ—C1—C7	120.1 (4)	H14C—C14A—H14D	105.6
C6—C1—C2ⁱⁱⁱ	118.9 (4)	C15A—C14A—H14C	104.4
C6—C1—C7	121.0 (4)	C15A—C14A—H14D	104.4
C1^iv—C2—H2	119.3	N2A—C14A—H14C	104.4
C3—C2—C1^iv	121.4 (4)	N2A—C14A—H14D	104.4
C3—C2—H2	119.3	N2A—C14A—C15A	131 (4)
O3—C8—O4	122.1 (4)	C14A—C15A—H15D	109.5
O3—C8—C3	119.9 (4)	C14A—C15A—H15E	109.5
O3—C8—Mn1	59.8 (2)	C14A—C15A—H15F	109.5
O4—C8—C3	117.9 (4)	H15D—C15A—H15E	109.5
O4—C8—Mn1	62.6 (2)	H15D—C15A—H15F	109.5
C3—C8—Mn1	170.9 (3)	H15E—C15A—H15F	109.5
H10A—C10—H10B	109.5	H10D—C10A—H10E	109.5
H10A—C10—H10C	109.5	H10D—C10A—H10F	109.5
H10B—C10—H10C	109.5	H10E—C10A—H10F	109.5
N1—C10—H10A	109.5	N1A—C10A—H10D	109.5
N1—C10—H10B	109.5	N1A—C10A—H10E	109.5
N1—C10—H10C	109.5	N1A—C10A—H10F	109.5
C12A—C11A—H11A	162.8	N1—C11—H11	125.8
N1A—C11A—H11A	127.1	N2—C11—N1	108.4 (7)
N1A—C11A—C12A	35.8 (9)	N2—C11—H11	125.8
N1A—C11A—N2A	105.8 (17)	C11A—N1A—C12A	109.4 (16)
N2A—C11A—H11A	127.1	C11A—N1A—C10A	126.8 (19)
N2A—C11A—C12A	70.1 (12)	C12A—N1A—C10A	123.7 (19)
C11A—C12A—H12A	159.6	C13—N2—C14	127.9 (7)
C13A—C12A—C11A	75.6 (10)	C11—N2—C14	121.9 (7)
C13A—C12A—H12A	124.8	C11—N2—C13	110.1 (7)
C13A—C12A—N1A	110.4 (15)	C9—O5—Mn1	94.5 (3)
N1A—C12A—C11A	34.8 (9)	C9—O6—Mn1	86.1 (3)
N1A—C12A—H12A	124.8	C11A—N2A—C13A	111.0 (17)
C12A—C13A—H13A	128.5	C11A—N2A—C14A	154 (2)
C12A—C13A—N2A	103.1 (14)	C13A—N2A—C14A	95 (2)
N2A—C13A—H13A	128.5	O1—Mn1—C9	110.20 (12)
H14A—C14—H14B	108.4	O1—Mn1—O3	84.29 (11)
C15—C14—H14A	110.0	O1—Mn1—C8	112.75 (12)
C15—C14—H14B	110.0	O1—Mn1—O4	141.76 (11)
N2—C14—H14A	110.0	O1—Mn1—O5	87.85 (12)
N2—C14—H14B	110.0	O1—Mn1—O6	132.57 (11)
N2—C14—C15	108.3 (8)	O2—Mn1—O1	98.81 (11)
C14—C15—H15A	109.5	O2—Mn1—C9	117.63 (13)
C14—C15—H15B	109.5	O2—Mn1—O3	98.62 (12)
C14—C15—H15C	109.5	O2—Mn1—C8	92.86 (12)
H15A—C15—H15B	109.5	O2—Mn1—O4	89.19 (11)
H15A—C15—H15C	109.5	O2—Mn1—O5	140.63 (12)
H15B—C15—H15C	109.5	O2—Mn1—O6	92.91 (12)
C8—O4—Mn1	88.3 (2)	O3—Mn1—C9	137.00 (13)
C6^iv—C5—C9^v	121.7 (4)	O3—Mn1—C8	28.47 (12)
C4—C5—C9^v	119.1 (4)	O3—Mn1—O4	57.49 (11)
C4—C5—C6^iv	119.2 (4)	O3—Mn1—O6	139.06 (12)
C1—C6—C5ⁱⁱⁱ	120.5 (4)	C8—Mn1—C9	121.49 (13)
C1—C6—H6	119.7	O4—Mn1—C9	98.50 (12)
C5ⁱⁱⁱ—C6—H6	119.7	O4—Mn1—C8	29.11 (11)
C2—C3—C8	120.2 (4)	O4—Mn1—O6	83.72 (11)
C4—C3—C2	118.8 (4)	O5—Mn1—C9	27.97 (12)
C4—C3—C8	121.0 (4)	O5—Mn1—O3	120.70 (13)
C5—C4—H4	119.5	O5—Mn1—C8	120.31 (13)
C3—C4—C5	121.0 (4)	O5—Mn1—O4	109.24 (13)
C3—C4—H4	119.5	O5—Mn1—O6	56.73 (11)
O1ⁱ—C7—C1	118.7 (4)	O6—Mn1—C9	28.82 (12)
O2—C7—O1ⁱ	123.3 (4)	O6—Mn1—C8	112.34 (13)
O2—C7—C1	118.0 (3)

C9^v—C5—C4—C3	174.4 (4)	C5ⁱⁱ—C9—O6—Mn1	172.5 (3)
O3—C8—O4—Mn1	6.1 (4)	C6—C1—C7—O1ⁱ	14.7 (6)
O3—C8—C3—C2	−4.7 (6)	C6—C1—C7—O2	−167.2 (4)
O3—C8—C3—C4	174.7 (4)	C6^iv—C5—C4—C3	−4.4 (6)
C1^iv—C2—C3—C8	−179.9 (4)	C3—C8—O4—Mn1	−169.7 (3)
C1^iv—C2—C3—C4	0.7 (6)	C7—C1—C6—C5ⁱⁱⁱ	−176.7 (4)
C2ⁱⁱⁱ—C1—C6—C5ⁱⁱⁱ	1.4 (6)	N1—C12—C13—N2	−1.5 (10)
C2ⁱⁱⁱ—C1—C7—O1ⁱ	−163.4 (4)	N1—C11—N2—C14	−178.7 (7)
C2ⁱⁱⁱ—C1—C7—O2	14.7 (6)	N1—C11—N2—C13	−1.7 (9)
C2—C3—C4—C5	3.0 (6)	C12—N1—C11—N2	0.7 (8)
C8—C3—C4—C5	−176.4 (4)	C12—C13—N2—C14	178.8 (8)
C10—N1—C12—C13	177.8 (9)	C12—C13—N2—C11	2.0 (10)
C10—N1—C11—N2	−176.6 (8)	C15A—C14A—N2A—C11A	114 (7)
C11A—C12A—C13A—N2A	3.2 (17)	C15A—C14A—N2A—C13A	−70 (6)
C11A—C12A—N1A—C10A	178 (4)	C11—N1—C12—C13	0.5 (9)
C12A—C11A—N1A—C10A	−178 (4)	N1A—C11A—N2A—C13A	5 (3)
C12A—C11A—N2A—C13A	3.5 (18)	N1A—C11A—N2A—C14A	−178 (6)
C12A—C11A—N2A—C14A	180 (7)	N1A—C12A—C13A—N2A	3 (3)
C12A—C13A—N2A—C11A	−5 (3)	O5—C9—O6—Mn1	−4.6 (4)
C12A—C13A—N2A—C14A	176 (2)	O6—C9—O5—Mn1	5.0 (5)
C13A—C12A—N1A—C11A	0 (3)	N2A—C11A—N1A—C12A	−3 (3)
C13A—C12A—N1A—C10A	177 (3)	N2A—C11A—N1A—C10A	179 (3)
C15—C14—N2—C13	53.0 (12)	Mn1—O2—C7—O1ⁱ	13.3 (5)
C15—C14—N2—C11	−130.5 (8)	Mn1—O2—C7—C1	−164.7 (3)
O4—C8—C3—C2	171.3 (4)	Mn1—O3—C8—O4	−6.3 (4)
O4—C8—C3—C4	−9.3 (6)	Mn1—O3—C8—C3	169.5 (3)
C5ⁱⁱ—C9—O5—Mn1	−172.1 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, −y+1, z−1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) −x+3/2, −y+1, z+1/2.

(c280k) top

Crystal data top

C₉H₃MnO₆·C₆H₁₁N₂	D_x = 1.611 Mg m⁻³
M_r = 373.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1836 reflections
a = 14.8837 (6) Å	θ = 2.5–29.3°
b = 12.4554 (5) Å	µ = 0.89 mm⁻¹
c = 16.6018 (5) Å	T = 280 K
V = 3077.69 (19) Å³	Prism, colorless
Z = 8	0.15 × 0.11 × 0.07 mm
F(000) = 1528

Data collection top

SuperNova, Single source at offset), Atlas diffractometer	3700 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2103 reflections with I > 2σ(I)
Detector resolution: 10.3590 pixels mm^-1	R_int = 0.069
ω scans	θ_max = 29.3°, θ_min = 2.5°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET) (compiled Mar 7 2011,18:06:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −18→15
T_min = 0.981, T_max = 1.000	k = −12→16
11023 measured reflections	l = −19→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.193	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0707P)² + 4.4689P] where P = (F_o² + 2F_c²)/3
3700 reflections	(Δ/σ)_max = 0.002
210 parameters	Δρ_max = 0.86 e Å⁻³
284 restraints	Δρ_min = −0.65 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5270 (2)	0.3805 (2)	0.50519 (18)	0.0322 (8)
O2	0.4989 (2)	0.5849 (3)	0.62392 (19)	0.0354 (8)
C9	0.7306 (3)	0.5773 (4)	0.4984 (3)	0.0338 (11)
O3	0.5934 (3)	0.3515 (3)	0.6698 (2)	0.0436 (9)
C2	0.5925 (3)	0.2700 (4)	0.8289 (3)	0.0285 (10)
H2	0.5568	0.2352	0.7911	0.034*
C8	0.6355 (3)	0.4019 (4)	0.7204 (3)	0.0289 (10)
N2A	0.376 (2)	0.407 (2)	0.8158 (15)	0.051 (6)*	0.172 (7)
C10	0.3890 (7)	0.2197 (8)	0.6293 (6)	0.091 (3)*	0.828 (7)
H10D	0.4363	0.1686	0.6376	0.136*	0.828 (7)
H10E	0.4047	0.2666	0.5856	0.136*	0.828 (7)
H10F	0.3343	0.1826	0.6165	0.136*	0.828 (7)
C11A	0.351 (2)	0.299 (2)	0.7991 (16)	0.045 (6)*	0.172 (7)
H11A	0.3218	0.2509	0.8331	0.054*	0.172 (7)
C12A	0.3973 (18)	0.3752 (16)	0.6819 (14)	0.025 (5)*	0.172 (7)
H12A	0.4080	0.3840	0.6271	0.031*	0.172 (7)
C13A	0.398 (3)	0.4513 (19)	0.7431 (17)	0.070 (6)*	0.172 (7)
H13A	0.4113	0.5235	0.7356	0.084*	0.172 (7)
C14	0.3865 (7)	0.5203 (9)	0.8257 (7)	0.098 (4)*	0.828 (7)
H14C	0.4182	0.5682	0.7895	0.118*	0.828 (7)
H14D	0.3276	0.5508	0.8359	0.118*	0.828 (7)
C15	0.4362 (9)	0.5128 (12)	0.9024 (8)	0.135 (5)*	0.828 (7)
H15D	0.4971	0.4918	0.8918	0.202*	0.828 (7)
H15E	0.4082	0.4604	0.9365	0.202*	0.828 (7)
H15F	0.4357	0.5814	0.9287	0.202*	0.828 (7)
O4	0.6712 (3)	0.4915 (3)	0.7051 (2)	0.0442 (9)
C5	0.7031 (3)	0.3708 (4)	0.9406 (3)	0.0305 (11)
C6	0.3469 (3)	0.7812 (4)	0.5375 (3)	0.0307 (11)
H6	0.3426	0.7544	0.4854	0.037*
C3	0.6411 (3)	0.3606 (4)	0.8063 (3)	0.0278 (10)
C4	0.6943 (3)	0.4119 (4)	0.8629 (3)	0.0290 (10)
H4	0.7246	0.4746	0.8488	0.035*
C1	0.4033 (3)	0.7311 (4)	0.5931 (3)	0.0271 (10)
C7	0.4614 (3)	0.6385 (4)	0.5689 (3)	0.0266 (10)
C12	0.3451 (5)	0.2444 (7)	0.7761 (5)	0.0533 (19)*	0.828 (7)
H12	0.3278	0.1743	0.7876	0.064*	0.828 (7)
C13	0.3433 (6)	0.3250 (7)	0.8301 (6)	0.070 (2)*	0.828 (7)
H13	0.3252	0.3237	0.8837	0.084*	0.828 (7)
C14A	0.342 (4)	0.401 (5)	0.897 (2)	0.133 (17)*	0.172 (7)
H14A	0.3145	0.3325	0.9084	0.159*	0.172 (7)
H14B	0.3005	0.4588	0.9086	0.159*	0.172 (7)
C15A	0.429 (4)	0.415 (7)	0.941 (4)	0.17 (2)*	0.172 (7)
H15A	0.4760	0.3769	0.9129	0.251*	0.172 (7)
H15B	0.4235	0.3866	0.9945	0.251*	0.172 (7)
H15C	0.4442	0.4897	0.9436	0.251*	0.172 (7)
Mn1	0.60414 (5)	0.48519 (5)	0.58091 (4)	0.0256 (2)
C10A	0.362 (6)	0.187 (4)	0.673 (4)	0.19 (3)*	0.172 (7)
H10A	0.3625	0.1243	0.7062	0.287*	0.172 (7)
H10B	0.4090	0.1821	0.6334	0.287*	0.172 (7)
H10C	0.3051	0.1932	0.6463	0.287*	0.172 (7)
C11	0.3937 (6)	0.3847 (7)	0.7196 (6)	0.060 (2)*	0.828 (7)
H11	0.4185	0.4331	0.6832	0.072*	0.828 (7)
N1	0.3770 (6)	0.2791 (6)	0.6983 (5)	0.067 (2)*	0.828 (7)
N1A	0.3771 (19)	0.2842 (16)	0.7239 (14)	0.029 (5)*	0.172 (7)
O5	0.7090 (3)	0.4841 (3)	0.4876 (2)	0.0541 (11)
O6	0.6977 (3)	0.6333 (3)	0.5527 (2)	0.0518 (10)
N2	0.3754 (6)	0.4103 (6)	0.7851 (5)	0.070 (2)*	0.828 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0405 (19)	0.0317 (18)	0.0243 (16)	0.0019 (14)	0.0035 (15)	−0.0046 (14)
O2	0.0439 (19)	0.0310 (18)	0.0312 (17)	0.0103 (14)	−0.0018 (15)	−0.0007 (14)
C9	0.032 (3)	0.044 (3)	0.026 (2)	−0.002 (2)	0.000 (2)	0.0021 (19)
O3	0.062 (2)	0.043 (2)	0.0264 (17)	−0.0089 (17)	−0.0065 (17)	0.0096 (15)
C2	0.030 (3)	0.029 (2)	0.026 (2)	−0.0036 (18)	−0.008 (2)	−0.0002 (19)
C8	0.024 (2)	0.035 (2)	0.028 (2)	0.0019 (18)	−0.0035 (18)	0.0093 (18)
O4	0.055 (2)	0.041 (2)	0.0370 (19)	−0.0104 (16)	−0.0105 (17)	0.0138 (16)
C5	0.033 (3)	0.032 (3)	0.026 (2)	−0.002 (2)	−0.005 (2)	−0.0013 (19)
C6	0.034 (3)	0.033 (3)	0.025 (2)	0.002 (2)	−0.007 (2)	−0.003 (2)
C3	0.028 (2)	0.027 (2)	0.029 (2)	−0.0012 (18)	−0.0035 (18)	0.0038 (17)
C4	0.029 (2)	0.027 (2)	0.030 (2)	−0.0030 (19)	−0.0022 (19)	0.0038 (18)
C1	0.026 (2)	0.025 (2)	0.030 (2)	0.0029 (17)	−0.004 (2)	−0.0016 (18)
C7	0.026 (2)	0.026 (2)	0.028 (2)	−0.0027 (17)	−0.0025 (19)	−0.0034 (18)
Mn1	0.0309 (4)	0.0252 (4)	0.0206 (4)	0.0001 (3)	0.0019 (3)	0.0012 (3)
O5	0.063 (3)	0.046 (2)	0.054 (2)	−0.0200 (19)	0.030 (2)	−0.0065 (18)
O6	0.068 (3)	0.044 (2)	0.043 (2)	−0.0084 (18)	0.026 (2)	−0.0010 (17)

Geometric parameters (Å, º) top

O1—C7ⁱ	1.265 (5)	C14—C15	1.475 (15)
O1—Mn1	2.145 (3)	C14—N2	1.536 (13)
O2—C7	1.262 (5)	O4—Mn1	2.292 (4)
O2—Mn1	2.123 (3)	C5—C9^iv	1.521 (7)
C9—C5ⁱⁱ	1.521 (7)	C5—C6ⁱⁱⁱ	1.390 (6)
C9—Mn1	2.595 (5)	C5—C4	1.395 (6)
C9—O5	1.218 (6)	C6—C5^v	1.390 (6)
C9—O6	1.240 (6)	C6—C1	1.394 (6)
O3—C8	1.221 (6)	C3—C4	1.385 (6)
O3—Mn1	2.231 (3)	C1—C2^v	1.385 (6)
C2—C3	1.392 (6)	C1—C7	1.497 (6)
C2—C1ⁱⁱⁱ	1.385 (6)	C7—O1ⁱ	1.265 (5)
C8—O4	1.263 (6)	C12—C13	1.347 (12)
C8—C3	1.517 (6)	C12—N1	1.442 (11)
C8—Mn1	2.581 (5)	C13—N2	1.383 (11)
N2A—C11A	1.417 (19)	C14A—C15A	1.49 (3)
N2A—C13A	1.367 (18)	Mn1—O5	2.198 (4)
N2A—C14A	1.44 (3)	Mn1—O6	2.358 (4)
C10—N1	1.375 (12)	C10A—N1A	1.49 (3)
C11A—N1A	1.324 (18)	C11—N1	1.384 (11)
C12A—C13A	1.389 (18)	C11—N2	1.166 (11)
C12A—N1A	1.364 (18)

C7ⁱ—O1—Mn1	127.6 (3)	O1—Mn1—C9	110.36 (14)
C7—O2—Mn1	113.1 (3)	O1—Mn1—O3	84.03 (12)
C5ⁱⁱ—C9—Mn1	172.5 (3)	O1—Mn1—C8	112.24 (14)
O5—C9—C5ⁱⁱ	118.9 (4)	O1—Mn1—O4	141.40 (12)
O5—C9—Mn1	57.6 (3)	O1—Mn1—O5	87.90 (14)
O5—C9—O6	122.6 (5)	O1—Mn1—O6	132.47 (13)
O6—C9—C5ⁱⁱ	118.4 (5)	O2—Mn1—O1	99.06 (13)
O6—C9—Mn1	65.1 (3)	O2—Mn1—C9	117.03 (15)
C8—O3—Mn1	92.0 (3)	O2—Mn1—O3	99.29 (14)
C1ⁱⁱⁱ—C2—C3	120.8 (4)	O2—Mn1—C8	93.83 (14)
O3—C8—O4	122.1 (4)	O2—Mn1—O4	89.93 (14)
O3—C8—C3	120.1 (4)	O2—Mn1—O5	139.85 (14)
O3—C8—Mn1	59.8 (2)	O2—Mn1—O6	92.59 (13)
O4—C8—C3	117.7 (4)	O3—Mn1—C9	136.95 (15)
O4—C8—Mn1	62.6 (2)	O3—Mn1—C8	28.22 (13)
C3—C8—Mn1	171.6 (3)	O3—Mn1—O4	57.43 (12)
C11A—N2A—C14A	93 (3)	O3—Mn1—O6	139.24 (14)
C13A—N2A—C11A	105.9 (18)	C8—Mn1—C9	121.35 (15)
C13A—N2A—C14A	158 (3)	O4—Mn1—C9	98.24 (14)
N1A—C11A—N2A	103.8 (19)	O4—Mn1—C8	29.29 (13)
N1A—C12A—C13A	101.2 (17)	O4—Mn1—O6	83.94 (13)
N2A—C13A—C12A	111.6 (18)	O5—Mn1—C9	27.89 (14)
C15—C14—N2	112.1 (10)	O5—Mn1—O3	120.80 (15)
C8—O4—Mn1	88.2 (3)	O5—Mn1—C8	120.11 (16)
C6ⁱⁱⁱ—C5—C9^iv	121.6 (4)	O5—Mn1—O4	108.95 (16)
C6ⁱⁱⁱ—C5—C4	119.1 (4)	O5—Mn1—O6	56.34 (13)
C4—C5—C9^iv	119.3 (4)	O6—Mn1—C9	28.49 (14)
C5^v—C6—C1	120.6 (4)	O6—Mn1—C8	112.72 (15)
C2—C3—C8	119.9 (4)	N2—C11—N1	117.1 (9)
C4—C3—C2	119.2 (4)	C10—N1—C12	128.9 (8)
C4—C3—C8	120.8 (4)	C10—N1—C11	134.5 (9)
C3—C4—C5	120.8 (4)	C11—N1—C12	96.6 (7)
C2^v—C1—C6	119.3 (4)	C11A—N1A—C12A	115.5 (18)
C2^v—C1—C7	119.6 (4)	C11A—N1A—C10A	127 (3)
C6—C1—C7	121.0 (4)	C12A—N1A—C10A	115 (3)
O1ⁱ—C7—C1	119.0 (4)	C9—O5—Mn1	94.5 (3)
O2—C7—O1ⁱ	123.0 (4)	C9—O6—Mn1	86.4 (3)
O2—C7—C1	118.0 (4)	C13—N2—C14	119.0 (9)
C13—C12—N1	112.3 (8)	C11—N2—C14	129.0 (9)
C12—C13—N2	101.9 (9)	C11—N2—C13	112.0 (9)
N2A—C14A—C15A	99 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, −y+1, z−1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+3/2, −y+1, z+1/2; (v) −x+1, y+1/2, −z+3/2.

(c300k) top

Crystal data top

C₉H₃MnO₆·1(C₆H₁₁N₂)	D_x = 1.606 Mg m⁻³
M_r = 373.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1787 reflections
a = 14.9204 (6) Å	θ = 2.5–29.4°
b = 12.4737 (5) Å	µ = 0.89 mm⁻¹
c = 16.5884 (6) Å	T = 300 K
V = 3087.3 (2) Å³	Prism, colorless
Z = 8	0.15 × 0.11 × 0.07 mm
F(000) = 1528

Data collection top

SuperNova, Single source at offset), Atlas diffractometer	3708 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2054 reflections with I > 2σ(I)
Detector resolution: 10.3590 pixels mm^-1	R_int = 0.071
ω scans	θ_max = 29.4°, θ_min = 2.5°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET) (compiled Mar 7 2011,18:06:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −18→15
T_min = 0.980, T_max = 1.000	k = −12→16
11042 measured reflections	l = −19→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0543P)² + 2.0156P] where P = (F_o² + 2F_c²)/3
3708 reflections	(Δ/σ)_max = 0.001
213 parameters	Δρ_max = 0.71 e Å⁻³
283 restraints	Δρ_min = −0.66 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C8	0.6353 (3)	0.4028 (3)	0.7216 (3)	0.0294 (9)
C9	0.7313 (3)	0.5777 (4)	0.4990 (3)	0.0352 (10)
C7	0.4613 (3)	0.6389 (3)	0.5679 (2)	0.0275 (9)
O1	0.5276 (2)	0.3805 (2)	0.50571 (17)	0.0350 (7)
C1	0.4032 (3)	0.7318 (3)	0.5925 (2)	0.0274 (9)
N1A	0.3748 (15)	0.2591 (14)	0.6764 (13)	0.045 (5)*	0.214 (8)
C10	0.3914 (9)	0.2210 (11)	0.6355 (8)	0.108 (4)*	0.786 (8)
H10D	0.4380	0.1696	0.6454	0.163*	0.786 (8)
H10E	0.4086	0.2669	0.5917	0.163*	0.786 (8)
H10F	0.3370	0.1842	0.6220	0.163*	0.786 (8)
C11A	0.3466 (19)	0.2289 (17)	0.7496 (14)	0.050 (5)*	0.214 (8)
H11A	0.3251	0.1612	0.7628	0.060*	0.214 (8)
C12A	0.3957 (13)	0.3679 (14)	0.6821 (12)	0.026 (4)*	0.214 (8)
H12A	0.4177	0.4090	0.6398	0.031*	0.214 (8)
C13A	0.3801 (17)	0.4054 (16)	0.7559 (14)	0.038 (5)*	0.214 (8)
H13A	0.3848	0.4757	0.7740	0.045*	0.214 (8)
C14	0.3853 (6)	0.5197 (8)	0.8213 (6)	0.098 (3)*	0.786 (8)
H14C	0.4173	0.5622	0.7816	0.118*	0.786 (8)
H14D	0.3268	0.5519	0.8297	0.118*	0.786 (8)
C15	0.4333 (9)	0.5182 (12)	0.8943 (9)	0.157 (5)*	0.786 (8)
H15D	0.4882	0.4792	0.8871	0.235*	0.786 (8)
H15E	0.3979	0.4839	0.9352	0.235*	0.786 (8)
H15F	0.4466	0.5903	0.9105	0.235*	0.786 (8)
O2	0.4986 (2)	0.5854 (2)	0.62340 (17)	0.0372 (7)
C4	0.6941 (3)	0.4125 (3)	0.8639 (2)	0.0317 (10)
H4	0.7244	0.4750	0.8500	0.038*
C5	0.7030 (3)	0.3704 (3)	0.9414 (2)	0.0305 (10)
C2	0.5922 (3)	0.2710 (3)	0.8294 (2)	0.0292 (10)
H2	0.5564	0.2364	0.7916	0.035*
C3	0.6404 (3)	0.3614 (3)	0.8073 (2)	0.0287 (9)
C6	0.3476 (3)	0.7810 (3)	0.5373 (3)	0.0318 (10)
H6	0.3439	0.7541	0.4851	0.038*
C12	0.3438 (6)	0.2491 (7)	0.7805 (5)	0.062 (2)*	0.786 (8)
H12	0.3263	0.1790	0.7913	0.074*	0.786 (8)
C13	0.3404 (7)	0.3252 (8)	0.8300 (7)	0.081 (3)*	0.786 (8)
H13	0.3184	0.3220	0.8824	0.097*	0.786 (8)
C14A	0.359 (3)	0.362 (4)	0.8825 (18)	0.150 (15)*	0.214 (8)
H14A	0.3496	0.3013	0.9177	0.180*	0.214 (8)
H14B	0.3027	0.4017	0.8845	0.180*	0.214 (8)
C15A	0.422 (3)	0.435 (5)	0.934 (3)	0.19 (2)*	0.214 (8)
H15A	0.3970	0.5056	0.9371	0.281*	0.214 (8)
H15B	0.4798	0.4373	0.9097	0.281*	0.214 (8)
H15C	0.4265	0.4052	0.9874	0.281*	0.214 (8)
O5	0.7082 (2)	0.4849 (3)	0.4887 (2)	0.0574 (10)
C10A	0.381 (3)	0.199 (3)	0.6064 (18)	0.076 (11)*	0.214 (8)
H10A	0.4338	0.1552	0.6084	0.113*	0.214 (8)
H10B	0.3842	0.2460	0.5607	0.113*	0.214 (8)
H10C	0.3291	0.1539	0.6015	0.113*	0.214 (8)
C11	0.3944 (6)	0.3879 (7)	0.7191 (6)	0.060 (2)*	0.786 (8)
H11	0.4168	0.4347	0.6804	0.072*	0.786 (8)
O3	0.5928 (2)	0.3525 (3)	0.67086 (18)	0.0472 (9)
O4	0.6704 (2)	0.4915 (3)	0.70604 (19)	0.0475 (9)
N1	0.3773 (4)	0.2851 (5)	0.7074 (4)	0.0569 (18)*	0.786 (8)
N2	0.3751 (5)	0.4134 (5)	0.7929 (5)	0.0669 (19)*	0.786 (8)
N2A	0.354 (2)	0.3119 (19)	0.8011 (13)	0.075 (6)*	0.214 (8)
O6	0.6983 (2)	0.6336 (3)	0.5535 (2)	0.0567 (10)
Mn1	0.60400 (4)	0.48558 (5)	0.58142 (4)	0.0271 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8	0.026 (2)	0.033 (2)	0.0295 (19)	−0.0001 (17)	−0.0041 (17)	0.0088 (17)
C9	0.036 (2)	0.044 (3)	0.026 (2)	−0.0003 (19)	0.0027 (19)	0.0044 (19)
C7	0.030 (2)	0.024 (2)	0.028 (2)	−0.0015 (16)	−0.0003 (18)	−0.0034 (17)
O1	0.0449 (19)	0.0333 (17)	0.0267 (15)	0.0009 (13)	0.0016 (14)	−0.0064 (13)
C1	0.032 (2)	0.022 (2)	0.028 (2)	0.0011 (16)	−0.0004 (19)	−0.0013 (17)
O2	0.0446 (18)	0.0362 (17)	0.0307 (16)	0.0127 (14)	−0.0015 (14)	−0.0005 (13)
C4	0.035 (2)	0.027 (2)	0.032 (2)	−0.0037 (18)	−0.0034 (19)	0.0011 (18)
C5	0.031 (2)	0.033 (2)	0.028 (2)	−0.0014 (19)	−0.0055 (19)	−0.0016 (18)
C2	0.032 (2)	0.029 (2)	0.027 (2)	−0.0023 (17)	−0.0086 (19)	0.0002 (18)
C3	0.032 (2)	0.027 (2)	0.0271 (19)	0.0000 (17)	−0.0039 (17)	0.0012 (16)
C6	0.036 (3)	0.030 (2)	0.029 (2)	0.0015 (19)	−0.004 (2)	−0.0026 (18)
O5	0.071 (2)	0.049 (2)	0.052 (2)	−0.0222 (18)	0.0304 (19)	−0.0074 (17)
O3	0.071 (2)	0.0433 (19)	0.0276 (16)	−0.0121 (16)	−0.0102 (16)	0.0095 (14)
O4	0.059 (2)	0.0448 (19)	0.0388 (18)	−0.0119 (16)	−0.0100 (16)	0.0158 (15)
O6	0.071 (2)	0.049 (2)	0.050 (2)	−0.0092 (18)	0.0296 (19)	−0.0006 (16)
Mn1	0.0333 (4)	0.0266 (4)	0.0215 (3)	0.0006 (3)	0.0021 (3)	0.0009 (3)

Geometric parameters (Å, º) top

C8—C3	1.514 (6)	C14—C15	1.409 (15)
C8—O3	1.226 (5)	C14—N2	1.415 (10)
C8—O4	1.251 (5)	O2—Mn1	2.123 (3)
C8—Mn1	2.587 (4)	C4—C5	1.395 (6)
C9—C5ⁱ	1.514 (6)	C4—C3	1.390 (6)
C9—O5	1.220 (5)	C5—C9^iv	1.514 (6)
C9—O6	1.243 (5)	C5—C6^v	1.392 (6)
C9—Mn1	2.607 (5)	C2—C1^v	1.386 (5)
C7—O1ⁱⁱ	1.256 (5)	C2—C3	1.388 (6)
C7—C1	1.504 (5)	C6—C5ⁱⁱⁱ	1.392 (6)
C7—O2	1.265 (5)	C12—C13	1.257 (12)
O1—C7ⁱⁱ	1.256 (5)	C12—N1	1.387 (9)
O1—Mn1	2.143 (3)	C13—N2	1.362 (11)
C1—C2ⁱⁱⁱ	1.386 (5)	C14A—C15A	1.56 (3)
C1—C6	1.380 (6)	C14A—N2A	1.49 (2)
N1A—C11A	1.339 (17)	O5—Mn1	2.187 (3)
N1A—C12A	1.396 (16)	C11—N1	1.321 (9)
N1A—C10A	1.39 (3)	C11—N2	1.297 (10)
C10—N1	1.450 (13)	O3—Mn1	2.232 (3)
C11A—N2A	1.347 (17)	O4—Mn1	2.293 (3)
C12A—C13A	1.330 (17)	O6—Mn1	2.368 (3)
C13A—N2A	1.438 (18)

C3—C8—Mn1	171.5 (3)	C8—O3—Mn1	92.2 (3)
O3—C8—C3	119.8 (4)	C8—O4—Mn1	88.7 (3)
O3—C8—O4	121.8 (4)	C12—N1—C10	126.3 (8)
O3—C8—Mn1	59.6 (2)	C11—N1—C10	128.9 (9)
O4—C8—C3	118.3 (4)	C11—N1—C12	104.8 (7)
O4—C8—Mn1	62.4 (2)	C13—N2—C14	130.3 (9)
C5ⁱ—C9—Mn1	172.3 (3)	C11—N2—C14	121.3 (8)
O5—C9—C5ⁱ	120.0 (4)	C11—N2—C13	108.3 (8)
O5—C9—O6	121.5 (4)	C11A—N2A—C13A	108.4 (16)
O5—C9—Mn1	56.6 (2)	C11A—N2A—C14A	154 (2)
O6—C9—C5ⁱ	118.4 (4)	C13A—N2A—C14A	97 (2)
O6—C9—Mn1	65.0 (2)	C9—O6—Mn1	86.6 (3)
O1ⁱⁱ—C7—C1	119.2 (4)	C8—Mn1—C9	121.06 (14)
O1ⁱⁱ—C7—O2	123.2 (4)	O1—Mn1—C8	112.23 (13)
O2—C7—C1	117.5 (3)	O1—Mn1—C9	110.47 (13)
C7ⁱⁱ—O1—Mn1	128.1 (3)	O1—Mn1—O5	87.91 (12)
C2ⁱⁱⁱ—C1—C7	119.8 (4)	O1—Mn1—O3	83.98 (11)
C6—C1—C7	120.6 (4)	O1—Mn1—O4	141.03 (11)
C6—C1—C2ⁱⁱⁱ	119.5 (4)	O1—Mn1—O6	132.70 (12)
C11A—N1A—C12A	106.3 (16)	O2—Mn1—C8	94.18 (12)
C11A—N1A—C10A	129 (2)	O2—Mn1—C9	116.93 (14)
C10A—N1A—C12A	124.7 (19)	O2—Mn1—O1	99.04 (11)
N1A—C11A—N2A	109.4 (18)	O2—Mn1—O5	139.41 (13)
C13A—C12A—N1A	111.4 (15)	O2—Mn1—O3	99.37 (12)
C12A—C13A—N2A	104.0 (15)	O2—Mn1—O4	90.30 (12)
C15—C14—N2	109.2 (10)	O2—Mn1—O6	92.69 (12)
C7—O2—Mn1	113.3 (3)	O5—Mn1—C8	120.17 (14)
C3—C4—C5	120.4 (4)	O5—Mn1—C9	27.75 (12)
C4—C5—C9^iv	118.8 (4)	O5—Mn1—O3	121.18 (14)
C6^v—C5—C9^iv	122.2 (4)	O5—Mn1—O4	109.10 (14)
C6^v—C5—C4	118.9 (4)	O5—Mn1—O6	56.13 (12)
C1^v—C2—C3	120.6 (4)	O3—Mn1—C8	28.26 (12)
C4—C3—C8	120.5 (4)	O3—Mn1—C9	136.94 (14)
C2—C3—C8	120.0 (4)	O3—Mn1—O4	57.12 (11)
C2—C3—C4	119.5 (4)	O3—Mn1—O6	138.98 (13)
C1—C6—C5ⁱⁱⁱ	120.9 (4)	O4—Mn1—C8	28.92 (12)
C13—C12—N1	109.9 (9)	O4—Mn1—C9	98.27 (13)
C12—C13—N2	107.4 (10)	O4—Mn1—O6	83.97 (12)
N2A—C14A—C15A	140 (4)	O6—Mn1—C8	112.36 (14)
C9—O5—Mn1	95.6 (3)	O6—Mn1—C9	28.41 (12)
N2—C11—N1	109.5 (8)

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+3/2, −y+1, z+1/2; (v) −x+1, y−1/2, −z+3/2.

(c320k) top

Crystal data top

C₉H₃MnO₆·C₆H₁₁N₂	D_x = 1.599 Mg m⁻³
M_r = 373.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1768 reflections
a = 14.9773 (6) Å	θ = 2.5–29.4°
b = 12.5017 (5) Å	µ = 0.89 mm⁻¹
c = 16.5629 (6) Å	T = 320 K
V = 3101.3 (2) Å³	Prism, colorless
Z = 8	0.15 × 0.11 × 0.07 mm
F(000) = 1528

Data collection top

SuperNova, Single source at offset), Atlas diffractometer	3720 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2006 reflections with I > 2σ(I)
Detector resolution: 10.3590 pixels mm^-1	R_int = 0.071
ω scans	θ_max = 29.4°, θ_min = 2.5°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET) (compiled Mar 7 2011,18:06:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −18→15
T_min = 0.982, T_max = 1.000	k = −12→16
11091 measured reflections	l = −19→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.200	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0672P)² + 5.9635P] where P = (F_o² + 2F_c²)/3
3720 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.79 e Å⁻³
287 restraints	Δρ_min = −0.56 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C9	0.7317 (4)	0.5786 (5)	0.5008 (3)	0.0398 (12)
O1	0.5281 (2)	0.3808 (3)	0.50679 (19)	0.0382 (9)
C8	0.6341 (3)	0.4040 (4)	0.7228 (3)	0.0326 (11)
O2	0.4992 (2)	0.5867 (3)	0.6227 (2)	0.0414 (9)
C2	0.5918 (3)	0.2721 (4)	0.8306 (3)	0.0328 (11)
H2	0.5560	0.2378	0.7927	0.039*
C7	0.4615 (3)	0.6389 (4)	0.5668 (3)	0.0297 (11)
N1A	0.374 (3)	0.2788 (19)	0.7178 (18)	0.057 (6)*	0.189 (8)
Mn1	0.60384 (5)	0.48631 (6)	0.58239 (4)	0.0298 (3)
C10	0.3894 (9)	0.2173 (11)	0.6263 (8)	0.112 (4)*	0.811 (8)
H10D	0.4350	0.1649	0.6360	0.167*	0.811 (8)
H10E	0.4070	0.2626	0.5823	0.167*	0.811 (8)
H10F	0.3345	0.1818	0.6130	0.167*	0.811 (8)
C11A	0.352 (2)	0.288 (2)	0.7950 (18)	0.052 (6)*	0.189 (8)
H11A	0.3264	0.2362	0.8279	0.062*	0.189 (8)
C12A	0.395 (2)	0.3746 (19)	0.6805 (15)	0.038 (5)*	0.189 (8)
H12A	0.4064	0.3881	0.6262	0.046*	0.189 (8)
C13A	0.394 (3)	0.444 (2)	0.7444 (18)	0.079 (6)*	0.189 (8)
H13A	0.4054	0.5173	0.7399	0.095*	0.189 (8)
C14	0.3838 (9)	0.5212 (11)	0.8169 (8)	0.126 (5)*	0.811 (8)
H14C	0.4154	0.5673	0.7794	0.151*	0.811 (8)
H14D	0.3250	0.5516	0.8262	0.151*	0.811 (8)
C15	0.4324 (12)	0.5159 (15)	0.8928 (11)	0.187 (7)*	0.811 (8)
H15D	0.3962	0.4812	0.9328	0.280*	0.811 (8)
H15E	0.4467	0.5870	0.9105	0.280*	0.811 (8)
H15F	0.4865	0.4761	0.8852	0.280*	0.811 (8)
O3	0.5930 (3)	0.3536 (3)	0.6717 (2)	0.0525 (11)
C5	0.7026 (3)	0.3697 (4)	0.9428 (3)	0.0353 (12)
C6	0.3475 (3)	0.7806 (4)	0.5357 (3)	0.0361 (12)
H6	0.3431	0.7532	0.4836	0.043*
C3	0.6400 (3)	0.3615 (4)	0.8084 (3)	0.0317 (11)
C4	0.6939 (3)	0.4122 (4)	0.8650 (3)	0.0343 (11)
H4	0.7242	0.4745	0.8512	0.041*
C1	0.4036 (3)	0.7325 (4)	0.5906 (3)	0.0314 (11)
C12	0.3439 (6)	0.2451 (8)	0.7727 (6)	0.067 (2)*	0.811 (8)
H12	0.3259	0.1755	0.7840	0.081*	0.811 (8)
C13	0.3420 (7)	0.3251 (9)	0.8256 (7)	0.081 (3)*	0.811 (8)
H13	0.3235	0.3237	0.8791	0.097*	0.811 (8)
C14A	0.342 (4)	0.415 (5)	0.899 (2)	0.152 (17)*	0.189 (8)
H14A	0.2952	0.3645	0.9135	0.183*	0.189 (8)
H14B	0.3179	0.4867	0.9026	0.183*	0.189 (8)
C15A	0.421 (5)	0.402 (7)	0.953 (5)	0.21 (2)*	0.189 (8)
H15A	0.4037	0.3650	1.0016	0.313*	0.189 (8)
H15B	0.4442	0.4714	0.9674	0.313*	0.189 (8)
H15C	0.4667	0.3618	0.9261	0.313*	0.189 (8)
O6	0.6989 (3)	0.6345 (3)	0.5547 (3)	0.0636 (12)
N2	0.3745 (7)	0.4116 (7)	0.7813 (6)	0.081 (2)*	0.811 (8)
C10A	0.365 (5)	0.190 (4)	0.661 (3)	0.16 (2)*	0.189 (8)
H10A	0.3609	0.2173	0.6073	0.246*	0.189 (8)
H10B	0.3121	0.1502	0.6740	0.246*	0.189 (8)
H10C	0.4162	0.1440	0.6656	0.246*	0.189 (8)
C11	0.3933 (7)	0.3829 (8)	0.7153 (7)	0.072 (3)*	0.811 (8)
H11	0.4183	0.4296	0.6778	0.086*	0.811 (8)
O4	0.6695 (3)	0.4928 (3)	0.7080 (2)	0.0538 (11)
O5	0.7075 (3)	0.4864 (3)	0.4896 (3)	0.0619 (12)
N1	0.3771 (8)	0.2800 (7)	0.6966 (6)	0.077 (3)*	0.811 (8)
N2A	0.374 (2)	0.393 (2)	0.8165 (16)	0.072 (6)*	0.189 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C9	0.037 (3)	0.047 (3)	0.035 (3)	−0.003 (2)	0.002 (2)	0.003 (2)
O1	0.049 (2)	0.038 (2)	0.0272 (17)	0.0002 (16)	0.0023 (16)	−0.0060 (15)
C8	0.029 (3)	0.037 (3)	0.031 (2)	−0.0001 (19)	−0.0045 (19)	0.0082 (18)
O2	0.047 (2)	0.040 (2)	0.0367 (19)	0.0122 (16)	−0.0019 (16)	−0.0011 (16)
C2	0.038 (3)	0.031 (3)	0.029 (2)	−0.004 (2)	−0.007 (2)	0.000 (2)
C7	0.029 (2)	0.025 (2)	0.035 (3)	−0.0023 (18)	−0.003 (2)	−0.0038 (19)
Mn1	0.0358 (5)	0.0297 (4)	0.0240 (4)	0.0009 (3)	0.0017 (3)	0.0011 (3)
O3	0.076 (3)	0.050 (2)	0.0314 (18)	−0.0133 (19)	−0.0128 (19)	0.0118 (16)
C5	0.034 (3)	0.038 (3)	0.033 (2)	−0.004 (2)	−0.007 (2)	−0.002 (2)
C6	0.042 (3)	0.038 (3)	0.028 (3)	0.006 (2)	−0.006 (2)	−0.006 (2)
C3	0.034 (3)	0.030 (2)	0.031 (2)	0.0001 (19)	−0.006 (2)	0.0046 (18)
C4	0.033 (3)	0.033 (3)	0.037 (2)	−0.006 (2)	−0.004 (2)	0.003 (2)
C1	0.034 (3)	0.029 (2)	0.031 (2)	0.0031 (19)	−0.003 (2)	−0.003 (2)
O6	0.081 (3)	0.054 (2)	0.056 (2)	−0.012 (2)	0.035 (2)	−0.0026 (19)
O4	0.067 (3)	0.049 (2)	0.046 (2)	−0.0156 (19)	−0.012 (2)	0.0177 (17)
O5	0.075 (3)	0.052 (2)	0.059 (2)	−0.023 (2)	0.034 (2)	−0.0080 (19)

Geometric parameters (Å, º) top

C9—Mn1	2.612 (5)	C14—H14C	0.9700
C9—C5ⁱ	1.520 (7)	C14—H14D	0.9700
C9—O6	1.237 (6)	C14—C15	1.454 (18)
C9—O5	1.222 (6)	C14—N2	1.499 (14)
O1—C7ⁱⁱ	1.253 (5)	C15—H15D	0.9600
O1—Mn1	2.144 (3)	C15—H15E	0.9600
C8—Mn1	2.583 (5)	C15—H15F	0.9600
C8—O3	1.222 (6)	C5—C9^iv	1.520 (7)
C8—C3	1.516 (7)	C5—C6ⁱⁱⁱ	1.389 (7)
C8—O4	1.254 (6)	C5—C4	1.400 (7)
O2—C7	1.266 (6)	C6—C5^v	1.389 (7)
O2—Mn1	2.116 (3)	C6—H6	0.9300
C2—H2	0.9300	C6—C1	1.377 (7)
C2—C3	1.381 (7)	C3—C4	1.390 (7)
C2—C1ⁱⁱⁱ	1.397 (6)	C4—H4	0.9300
C7—O1ⁱⁱ	1.253 (5)	C1—C2^v	1.397 (6)
C7—C1	1.510 (6)	C12—H12	0.9300
N1A—C11A	1.328 (19)	C12—C13	1.329 (13)
N1A—C12A	1.382 (19)	C12—N1	1.423 (12)
N1A—C10A	1.46 (3)	C13—H13	0.9300
Mn1—O3	2.228 (4)	C13—N2	1.394 (13)
Mn1—O6	2.381 (4)	C14A—H14A	0.9700
Mn1—O4	2.303 (4)	C14A—H14B	0.9700
Mn1—O5	2.185 (4)	C14A—C15A	1.50 (2)
C10—H10D	0.9600	C14A—N2A	1.470 (19)
C10—H10E	0.9600	C15A—H15A	0.9600
C10—H10F	0.9600	C15A—H15B	0.9600
C10—N1	1.416 (14)	C15A—H15C	0.9600
C11A—H11A	0.9300	N2—C11	1.185 (12)
C11A—N2A	1.400 (19)	C10A—H10A	0.9600
C12A—H12A	0.9300	C10A—H10B	0.9600
C12A—C13A	1.372 (18)	C10A—H10C	0.9600
C13A—H13A	0.9300	C11—H11	0.9300
C13A—N2A	1.388 (19)	C11—N1	1.346 (12)

C5ⁱ—C9—Mn1	171.8 (4)	C15—C14—H14C	109.6
O6—C9—Mn1	65.5 (3)	C15—C14—H14D	109.6
O6—C9—C5ⁱ	118.2 (5)	C15—C14—N2	110.2 (12)
O5—C9—Mn1	56.3 (3)	N2—C14—H14C	109.6
O5—C9—C5ⁱ	119.8 (5)	N2—C14—H14D	109.6
O5—C9—O6	121.7 (5)	C14—C15—H15D	109.5
C7ⁱⁱ—O1—Mn1	128.5 (3)	C14—C15—H15E	109.5
O3—C8—Mn1	59.5 (3)	C14—C15—H15F	109.5
O3—C8—C3	119.8 (4)	H15D—C15—H15E	109.5
O3—C8—O4	122.2 (5)	H15D—C15—H15F	109.5
C3—C8—Mn1	172.5 (4)	H15E—C15—H15F	109.5
O4—C8—Mn1	63.0 (3)	C8—O3—Mn1	92.3 (3)
O4—C8—C3	117.9 (5)	C6ⁱⁱⁱ—C5—C9^iv	121.9 (5)
C7—O2—Mn1	113.9 (3)	C6ⁱⁱⁱ—C5—C4	119.4 (5)
C3—C2—H2	119.7	C4—C5—C9^iv	118.7 (5)
C3—C2—C1ⁱⁱⁱ	120.6 (4)	C5^v—C6—H6	119.7
C1ⁱⁱⁱ—C2—H2	119.7	C1—C6—C5^v	120.6 (5)
O1ⁱⁱ—C7—O2	123.7 (4)	C1—C6—H6	119.7
O1ⁱⁱ—C7—C1	118.5 (4)	C2—C3—C8	120.1 (4)
O2—C7—C1	117.7 (4)	C2—C3—C4	119.5 (4)
C11A—N1A—C12A	114.2 (19)	C4—C3—C8	120.3 (4)
C11A—N1A—C10A	131 (3)	C5—C4—H4	119.9
C12A—N1A—C10A	113 (3)	C3—C4—C5	120.1 (5)
O1—Mn1—C9	110.94 (16)	C3—C4—H4	119.9
O1—Mn1—C8	111.93 (15)	C2^v—C1—C7	119.4 (4)
O1—Mn1—O3	83.72 (13)	C6—C1—C2^v	119.6 (4)
O1—Mn1—O6	133.08 (14)	C6—C1—C7	121.1 (4)
O1—Mn1—O4	140.83 (13)	C13—C12—H12	124.5
O1—Mn1—O5	88.03 (15)	C13—C12—N1	111.1 (9)
C8—Mn1—C9	120.88 (16)	N1—C12—H12	124.5
O2—Mn1—C9	116.38 (16)	C12—C13—H13	128.3
O2—Mn1—O1	99.06 (14)	C12—C13—N2	103.3 (9)
O2—Mn1—C8	94.70 (15)	N2—C13—H13	128.3
O2—Mn1—O3	100.25 (15)	H14A—C14A—H14B	108.7
O2—Mn1—O6	92.40 (15)	C15A—C14A—H14A	110.5
O2—Mn1—O4	90.57 (15)	C15A—C14A—H14B	110.5
O2—Mn1—O5	138.42 (16)	N2A—C14A—H14A	110.5
O3—Mn1—C9	136.53 (17)	N2A—C14A—H14B	110.5
O3—Mn1—C8	28.21 (14)	N2A—C14A—C15A	106 (5)
O3—Mn1—O6	138.66 (16)	C14A—C15A—H15A	109.5
O3—Mn1—O4	57.16 (13)	C14A—C15A—H15B	109.5
O6—Mn1—C9	28.20 (15)	C14A—C15A—H15C	109.5
O6—Mn1—C8	112.23 (16)	H15A—C15A—H15B	109.5
O4—Mn1—C9	98.01 (16)	H15A—C15A—H15C	109.5
O4—Mn1—C8	29.02 (14)	H15B—C15A—H15C	109.5
O4—Mn1—O6	83.76 (15)	C9—O6—Mn1	86.3 (3)
O5—Mn1—C9	27.72 (15)	C13—N2—C14	122.3 (11)
O5—Mn1—C8	120.60 (17)	C11—N2—C14	128.2 (11)
O5—Mn1—O3	121.29 (17)	C11—N2—C13	109.5 (10)
O5—Mn1—O6	55.90 (14)	N1A—C10A—H10A	109.5
O5—Mn1—O4	109.42 (17)	N1A—C10A—H10B	109.5
H10D—C10—H10E	109.5	N1A—C10A—H10C	109.5
H10D—C10—H10F	109.5	H10A—C10A—H10B	109.5
H10E—C10—H10F	109.5	H10A—C10A—H10C	109.5
N1—C10—H10D	109.5	H10B—C10A—H10C	109.5
N1—C10—H10E	109.5	N2—C11—H11	121.4
N1—C10—H10F	109.5	N2—C11—N1	117.2 (11)
N1A—C11A—H11A	127.2	N1—C11—H11	121.4
N1A—C11A—N2A	106 (2)	C8—O4—Mn1	88.0 (3)
N2A—C11A—H11A	127.2	C9—O5—Mn1	96.0 (3)
N1A—C12A—H12A	129.1	C10—N1—C12	127.2 (10)
C13A—C12A—N1A	101.8 (17)	C11—N1—C10	134.0 (11)
C13A—C12A—H12A	129.1	C11—N1—C12	98.8 (9)
C12A—C13A—H13A	124.0	C11A—N2A—C14A	109 (3)
C12A—C13A—N2A	111.9 (18)	C13A—N2A—C11A	105.3 (18)
N2A—C13A—H13A	124.0	C13A—N2A—C14A	142 (3)
H14C—C14—H14D	108.1

C9^iv—C5—C4—C3	174.7 (5)	C5^v—C6—C1—C2^v	1.8 (8)
O1ⁱⁱ—C7—C1—C2^v	−164.5 (5)	C5^v—C6—C1—C7	−177.1 (4)
O1ⁱⁱ—C7—C1—C6	14.5 (7)	C6ⁱⁱⁱ—C5—C4—C3	−4.1 (8)
C8—C3—C4—C5	−176.8 (5)	C3—C8—O3—Mn1	171.3 (4)
O2—C7—C1—C2^v	13.3 (7)	C3—C8—O4—Mn1	−171.6 (4)
O2—C7—C1—C6	−167.7 (5)	C1ⁱⁱⁱ—C2—C3—C8	−179.7 (5)
C2—C3—C4—C5	3.1 (7)	C1ⁱⁱⁱ—C2—C3—C4	0.4 (7)
N1A—C11A—N2A—C13A	10 (4)	C12—C13—N2—C14	179.5 (10)
N1A—C11A—N2A—C14A	174 (4)	C12—C13—N2—C11	−1.5 (12)
N1A—C12A—C13A—N2A	0 (4)	C13—C12—N1—C10	179.3 (13)
Mn1—O2—C7—O1ⁱⁱ	13.2 (6)	C13—C12—N1—C11	1.1 (12)
Mn1—O2—C7—C1	−164.4 (3)	C13—N2—C11—N1	2.5 (15)
C11A—N1A—C12A—C13A	7 (5)	C15A—C14A—N2A—C11A	99 (6)
C12A—N1A—C11A—N2A	−11 (5)	C15A—C14A—N2A—C13A	−107 (7)
C12A—C13A—N2A—C11A	−7 (4)	O6—C9—O5—Mn1	2.8 (6)
C12A—C13A—N2A—C14A	−161 (5)	N2—C11—N1—C10	179.7 (14)
C14—N2—C11—N1	−178.6 (11)	N2—C11—N1—C12	−2.2 (14)
C15—C14—N2—C13	51.0 (16)	C10A—N1A—C11A—N2A	−178 (6)
C15—C14—N2—C11	−127.7 (15)	C10A—N1A—C12A—C13A	176 (5)
O3—C8—C3—C2	−6.4 (8)	O4—C8—O3—Mn1	−5.9 (6)
O3—C8—C3—C4	173.5 (5)	O4—C8—C3—C2	170.9 (5)
O3—C8—O4—Mn1	5.7 (5)	O4—C8—C3—C4	−9.2 (7)
C5ⁱ—C9—O6—Mn1	171.8 (4)	O5—C9—O6—Mn1	−2.6 (6)
C5ⁱ—C9—O5—Mn1	−171.5 (4)	N1—C12—C13—N2	0.1 (11)

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+3/2, −y+1, z+1/2; (v) −x+1, y+1/2, −z+3/2.

(c340k) top

Crystal data top

C₉H₃MnO₆·1(C₆H₁₁N₂)	D_x = 1.591 Mg m⁻³
M_r = 373.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1712 reflections
a = 15.0401 (7) Å	θ = 2.4–29.3°
b = 12.5366 (5) Å	µ = 0.88 mm⁻¹
c = 16.5320 (6) Å	T = 340 K
V = 3117.1 (2) Å³	Prism, colorless
Z = 8	0.15 × 0.11 × 0.07 mm
F(000) = 1528

Data collection top

SuperNova, Single source at offset), Atlas diffractometer	3747 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1947 reflections with I > 2σ(I)
Detector resolution: 10.3590 pixels mm^-1	R_int = 0.073
ω scans	θ_max = 29.4°, θ_min = 2.5°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET) (compiled Mar 7 2011,18:06:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −18→15
T_min = 0.979, T_max = 1.000	k = −16→13
11134 measured reflections	l = −22→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.193	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0694P)² + 1.6376P] where P = (F_o² + 2F_c²)/3
3747 reflections	(Δ/σ)_max = 0.006
213 parameters	Δρ_max = 0.56 e Å⁻³
288 restraints	Δρ_min = −0.53 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C9	0.7312 (3)	0.5796 (4)	0.5019 (3)	0.0422 (12)
O1	0.5287 (2)	0.3808 (2)	0.50790 (18)	0.0405 (8)
C8	0.6333 (3)	0.4053 (4)	0.7246 (3)	0.0332 (10)
O2	0.4999 (2)	0.5892 (2)	0.62165 (19)	0.0441 (8)
C2	0.5915 (3)	0.2729 (3)	0.8326 (3)	0.0346 (11)
H2	0.5556	0.2390	0.7947	0.042*
C7	0.4612 (3)	0.6398 (3)	0.5662 (3)	0.0324 (10)
N1A	0.3739 (16)	0.2614 (15)	0.6707 (13)	0.066 (5)*	0.255 (9)
Mn1	0.60380 (5)	0.48718 (5)	0.58350 (4)	0.0313 (3)
C10A	0.377 (3)	0.200 (3)	0.6014 (18)	0.090 (11)*	0.255 (9)
H10A	0.3843	0.2457	0.5552	0.136*	0.255 (9)
H10B	0.3235	0.1598	0.5963	0.136*	0.255 (9)
H10C	0.4271	0.1522	0.6046	0.136*	0.255 (9)
C12	0.3439 (7)	0.2539 (9)	0.7807 (6)	0.070 (3)*	0.745 (9)
H12	0.3282	0.1848	0.7951	0.084*	0.745 (9)
C13	0.3394 (8)	0.3301 (9)	0.8245 (8)	0.086 (3)*	0.745 (9)
H13	0.3161	0.3305	0.8766	0.103*	0.745 (9)
C14	0.3810 (9)	0.5205 (11)	0.8100 (9)	0.135 (5)*	0.745 (9)
H14D	0.4099	0.5615	0.7678	0.162*	0.745 (9)
H14C	0.3222	0.5503	0.8187	0.162*	0.745 (9)
C15	0.4303 (13)	0.5274 (17)	0.8812 (13)	0.221 (8)*	0.745 (9)
H15D	0.4921	0.5161	0.8693	0.331*	0.745 (9)
H15E	0.4103	0.4740	0.9186	0.331*	0.745 (9)
H15F	0.4226	0.5968	0.9047	0.331*	0.745 (9)
O3	0.5928 (3)	0.3554 (3)	0.6734 (2)	0.0594 (11)
C5	0.7018 (3)	0.3698 (4)	0.9444 (3)	0.0372 (11)
C6	0.3477 (3)	0.7807 (4)	0.5345 (3)	0.0377 (11)
H6	0.3431	0.7532	0.4824	0.045*
C3	0.6395 (3)	0.3634 (4)	0.8098 (3)	0.0336 (10)
C4	0.6934 (3)	0.4125 (4)	0.8671 (3)	0.0359 (11)
H4	0.7242	0.4743	0.8536	0.043*
C1	0.4037 (3)	0.7323 (4)	0.5894 (3)	0.0315 (10)
C12A	0.3994 (14)	0.3687 (14)	0.6734 (13)	0.046 (5)*	0.255 (9)
H12A	0.4239	0.4053	0.6298	0.055*	0.255 (9)
C13A	0.3847 (17)	0.4127 (15)	0.7459 (14)	0.048 (5)*	0.255 (9)
H13A	0.3872	0.4841	0.7608	0.058*	0.255 (9)
C14A	0.353 (4)	0.349 (3)	0.8789 (16)	0.195 (16)*	0.255 (9)
H14A	0.3603	0.2825	0.9082	0.234*	0.255 (9)
H14B	0.2912	0.3695	0.8854	0.234*	0.255 (9)
C15A	0.407 (4)	0.432 (5)	0.924 (3)	0.21 (2)*	0.255 (9)
H15A	0.4629	0.4011	0.9403	0.319*	0.255 (9)
H15B	0.3751	0.4545	0.9713	0.319*	0.255 (9)
H15C	0.4179	0.4919	0.8896	0.319*	0.255 (9)
O6	0.6998 (3)	0.6354 (3)	0.5569 (2)	0.0687 (12)
N2	0.3735 (5)	0.4140 (7)	0.7857 (6)	0.075 (2)*	0.745 (9)
C11	0.3922 (7)	0.3850 (9)	0.7118 (7)	0.072 (3)*	0.745 (9)
H11	0.4133	0.4296	0.6711	0.086*	0.745 (9)
C11A	0.3474 (18)	0.2376 (18)	0.7475 (14)	0.063 (5)*	0.255 (9)
H11A	0.3221	0.1738	0.7648	0.075*	0.255 (9)
O4	0.6680 (3)	0.4933 (3)	0.7097 (2)	0.0569 (10)
O5	0.7069 (3)	0.4888 (3)	0.4906 (3)	0.0674 (12)
N1	0.3765 (5)	0.2846 (6)	0.7046 (5)	0.064 (2)*	0.745 (9)
N2A	0.365 (2)	0.3236 (19)	0.7937 (13)	0.101 (6)*	0.255 (9)
C10	0.3917 (12)	0.2136 (15)	0.6349 (11)	0.144 (6)*	0.745 (9)
H10D	0.4415	0.1679	0.6459	0.217*	0.745 (9)
H10E	0.4038	0.2556	0.5877	0.217*	0.745 (9)
H10F	0.3397	0.1709	0.6258	0.217*	0.745 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C9	0.041 (3)	0.050 (3)	0.035 (2)	0.000 (2)	0.001 (2)	0.004 (2)
O1	0.053 (2)	0.0370 (18)	0.0317 (18)	0.0033 (15)	0.0030 (16)	−0.0078 (14)
C8	0.031 (2)	0.037 (2)	0.031 (2)	0.0011 (18)	−0.0054 (18)	0.0101 (18)
O2	0.055 (2)	0.0401 (19)	0.0375 (18)	0.0163 (15)	−0.0052 (16)	−0.0034 (15)
C2	0.039 (3)	0.034 (3)	0.031 (2)	−0.0052 (19)	−0.007 (2)	0.000 (2)
C7	0.035 (2)	0.029 (2)	0.033 (3)	−0.0022 (18)	−0.003 (2)	−0.0018 (19)
Mn1	0.0378 (4)	0.0311 (4)	0.0248 (4)	0.0009 (3)	0.0024 (3)	0.0019 (3)
O3	0.091 (3)	0.055 (2)	0.0320 (17)	−0.0172 (19)	−0.0122 (19)	0.0103 (16)
C5	0.038 (3)	0.041 (3)	0.033 (2)	−0.003 (2)	−0.010 (2)	−0.002 (2)
C6	0.046 (3)	0.037 (3)	0.029 (2)	0.007 (2)	−0.007 (2)	−0.003 (2)
C3	0.032 (2)	0.039 (3)	0.030 (2)	−0.0024 (19)	−0.0007 (19)	0.0056 (18)
C4	0.038 (3)	0.033 (3)	0.037 (2)	−0.004 (2)	−0.002 (2)	0.0014 (19)
C1	0.035 (2)	0.029 (2)	0.030 (2)	−0.0008 (18)	0.002 (2)	0.0020 (19)
O6	0.090 (3)	0.058 (2)	0.059 (2)	−0.013 (2)	0.040 (2)	−0.0002 (19)
O4	0.073 (3)	0.053 (2)	0.045 (2)	−0.0158 (18)	−0.0111 (19)	0.0173 (17)
O5	0.084 (3)	0.057 (2)	0.061 (2)	−0.029 (2)	0.036 (2)	−0.0077 (19)

Geometric parameters (Å, º) top

C9—Mn1	2.614 (5)	Mn1—O5	2.182 (4)
C9—C5ⁱ	1.523 (7)	C12—C13	1.200 (14)
C9—O6	1.240 (6)	C12—N1	1.404 (11)
C9—O5	1.211 (6)	C13—N2	1.334 (13)
O1—C7ⁱⁱ	1.261 (5)	C14—C15	1.39 (2)
O1—Mn1	2.148 (3)	C14—N2	1.399 (14)
C8—Mn1	2.587 (4)	C5—C9^iv	1.523 (7)
C8—O3	1.215 (5)	C5—C6ⁱⁱⁱ	1.388 (6)
C8—C3	1.507 (6)	C5—C4	1.391 (6)
C8—O4	1.245 (5)	C6—C5^v	1.388 (6)
O2—C7	1.257 (5)	C6—C1	1.379 (6)
O2—Mn1	2.116 (3)	C3—C4	1.390 (6)
C2—C3	1.396 (6)	C1—C2^v	1.389 (6)
C2—C1ⁱⁱⁱ	1.389 (6)	C12A—C13A	1.338 (17)
C7—O1ⁱⁱ	1.261 (5)	C13A—N2A	1.401 (17)
C7—C1	1.496 (6)	C14A—C15A	1.52 (2)
N1A—C10A	1.38 (3)	C14A—N2A	1.455 (17)
N1A—C12A	1.401 (17)	N2—C11	1.306 (12)
N1A—C11A	1.364 (18)	C11—N1	1.286 (11)
Mn1—O3	2.228 (3)	C11A—N2A	1.346 (17)
Mn1—O6	2.394 (4)	N1—C10	1.473 (18)
Mn1—O4	2.300 (4)

C5ⁱ—C9—Mn1	172.4 (4)	O4—Mn1—C9	98.38 (15)
O6—C9—Mn1	66.0 (3)	O4—Mn1—C8	28.77 (13)
O6—C9—C5ⁱ	118.3 (5)	O4—Mn1—O6	83.55 (14)
O5—C9—Mn1	56.0 (3)	O5—Mn1—C9	27.39 (14)
O5—C9—C5ⁱ	119.7 (5)	O5—Mn1—C8	121.09 (16)
O5—C9—O6	121.9 (5)	O5—Mn1—O3	121.94 (16)
C7ⁱⁱ—O1—Mn1	129.0 (3)	O5—Mn1—O6	55.60 (13)
O3—C8—Mn1	59.4 (2)	O5—Mn1—O4	109.88 (16)
O3—C8—C3	120.2 (4)	C13—C12—N1	110.0 (10)
O3—C8—O4	121.9 (4)	C12—C13—N2	108.4 (12)
C3—C8—Mn1	172.8 (3)	C15—C14—N2	110.1 (14)
O4—C8—Mn1	62.7 (2)	C8—O3—Mn1	92.6 (3)
O4—C8—C3	117.9 (4)	C6ⁱⁱⁱ—C5—C9^iv	122.2 (4)
C7—O2—Mn1	115.4 (3)	C6ⁱⁱⁱ—C5—C4	119.5 (4)
C1ⁱⁱⁱ—C2—C3	121.5 (4)	C4—C5—C9^iv	118.3 (4)
O1ⁱⁱ—C7—C1	118.5 (4)	C1—C6—C5^v	121.1 (4)
O2—C7—O1ⁱⁱ	123.3 (4)	C2—C3—C8	120.3 (4)
O2—C7—C1	118.2 (4)	C4—C3—C8	121.2 (4)
C10A—N1A—C12A	123.4 (19)	C4—C3—C2	118.5 (4)
C11A—N1A—C10A	132 (2)	C3—C4—C5	120.6 (4)
C11A—N1A—C12A	105.1 (16)	C2^v—C1—C7	119.4 (4)
O1—Mn1—C9	111.11 (15)	C6—C1—C2^v	118.8 (4)
O1—Mn1—C8	111.61 (14)	C6—C1—C7	121.7 (4)
O1—Mn1—O3	83.62 (13)	C13A—C12A—N1A	112.3 (16)
O1—Mn1—O6	133.78 (13)	C12A—C13A—N2A	102.3 (15)
O1—Mn1—O4	140.27 (12)	N2A—C14A—C15A	124 (4)
O1—Mn1—O5	88.26 (14)	C9—O6—Mn1	85.8 (3)
C8—Mn1—C9	121.04 (15)	C13—N2—C14	130.3 (11)
O2—Mn1—C9	115.31 (15)	C11—N2—C13	108.2 (9)
O2—Mn1—O1	99.21 (12)	C11—N2—C14	121.1 (10)
O2—Mn1—C8	95.62 (14)	N1—C11—N2	108.6 (9)
O2—Mn1—O3	101.20 (14)	N2A—C11A—N1A	107.3 (18)
O2—Mn1—O6	91.80 (14)	C8—O4—Mn1	88.5 (3)
O2—Mn1—O4	91.11 (14)	C9—O5—Mn1	96.6 (3)
O2—Mn1—O5	136.81 (15)	C12—N1—C10	126.1 (10)
O3—Mn1—C9	136.67 (16)	C11—N1—C12	104.4 (9)
O3—Mn1—C8	27.99 (13)	C11—N1—C10	129.5 (11)
O3—Mn1—O6	137.97 (15)	C13A—N2A—C14A	113.4 (18)
O3—Mn1—O4	56.70 (13)	C11A—N2A—C13A	111.1 (16)
O6—Mn1—C9	28.24 (14)	C11A—N2A—C14A	135 (2)
O6—Mn1—C8	111.74 (15)

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+3/2, −y+1, z+1/2; (v) −x+1, y+1/2, −z+3/2.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text