Effect of disordered imidazole substructure on proton dynamics in imidazolium malonic acid salt

The influence of a disorder in cation substructure on proton conductivity of imidazolium malonate (Im-MAL) is studied. Imidazolium in salts with dicarboxylic acids have been found to have a well ordered hydrogen-bond network and only in Im-MAL [Pogorzelec-Glaser et al. (2006). Mater. Sci.-Pol. (2006), 24, 245–252] were two types of cation observed: ordered Im-I and disordered Im-II. Im-I is involved in hydrogen bonds with malonic acid molecules, whereas Im-II is disordered between two symmetrically equivalent positions with occupancy of 0.5. NMR studies by Mizuno et al. [Hyperfine Interact. (2015), 230, 95–100] showed an 180° flip of ordered Im-I and calculated contribution of Im-I flipping to proton conductivity of Im-MAL. Ławniczak et al. [Solid State Ionics (2017), 306, 25] reported that temperature variation of the proton conductivity by impedance spectroscopy yielded the conductivity value higher than that calculated by Mizuno for Im-I. Moreover these detailed structure studies at 240 K and 280 K excluded any phase transition. Repeated X-ray studies from 14 K to 360 K show a continuous increase in anisotropic displacement factors. The half-occupied hydrogen bonds linking the Im-II nitro­gen atoms with hydroxyl oxygen atoms may be considered as electric dipoles and the interbond proton transfer as dipolar switching. It assumed here a coherent switching at low temperatures and a decrease of the coupling at higher temperatures with the disappearance at cross-over temperature at 318 K. The possible proton pathway in the crystal structure is determined and the contribution of the proton dynamics of Im-II to phonon-assisted proton diffusion in the ordered substructure is estimated.

Computing details

For all structures, data collection: CrysAlis v171.33.42; cell refinement: CrysAlis v171.33.42; data reduction: CrysAlis v171.33.42; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013). Molecular graphics: Diamond 3.2 for im14, m120, m295; DIAMOND 3.2 for m330.

(im14)

Crystal data

C6H5O8·3(C3H5N2)	Z = 2
Mr = 206.18	F(000) = 216
Triclinic, P1	Dx = 1.466 Mg m^−3
a = 6.9050 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3940 (13) Å	Cell parameters from 3204 reflections
c = 9.3390 (6) Å	θ = 4–56.0°
α = 117.560 (12)°	µ = 0.12 mm^−1
β = 102.07 (2)°	T = 14 K
γ = 89.390 (15)°	Unshaped, colorless
V = 466.94 (13) Å^3	0.34 × 0.32 × 0.21 mm

Data collection

Xcalibur Oxford Diffraction diffractometer	1826 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
CCD scans	θmax = 30.8°, θmin = 3.0°
Absorption correction: numerical CrysAlis v171.33.42	h = −7→9
Tmin = 0.921, Tmax = 1.231	k = −8→12
3204 measured reflections	l = −12→10
2245 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.030P)^2 + 0.6P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.123	(Δ/σ)max = 0.024
S = 1.17	Δρmax = 0.42 e Å^−3
2245 reflections	Δρmin = −0.35 e Å^−3
204 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
4 restraints	Extinction coefficient: 0.041 (2)

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.22167 (9)	0.42469 (8)	0.38829 (8)	0.01345 (16)
O2	0.21679 (9)	0.17206 (8)	0.16231 (8)	0.01342 (16)
O3	0.33589 (10)	0.14902 (9)	0.65169 (8)	0.01567 (17)
O4	0.08665 (9)	0.05863 (9)	0.42671 (8)	0.01508 (17)
C1	0.26845 (12)	0.26749 (11)	0.31685 (10)	0.0103 (2)
C2	0.39089 (12)	0.19424 (11)	0.42499 (11)	0.0127 (2)
C3	0.26537 (12)	0.13193 (11)	0.51236 (11)	0.0118 (2)
N1A1	0.29122 (11)	0.62517 (10)	0.71700 (9)	0.01177 (19)
C1A	0.23234 (12)	0.78718 (11)	0.78878 (11)	0.0110 (2)
N1A2	0.30047 (11)	0.85629 (10)	0.95172 (9)	0.01212 (19)
C2A	0.40725 (13)	0.73442 (11)	0.98654 (11)	0.0126 (2)
C3A	0.40091 (13)	0.58992 (11)	0.83894 (11)	0.0137 (2)
N1B1	0.0699 (2)	0.40913 (19)	1.05004 (18)	0.0106 (4)	0.5
C1B	0.0045 (3)	0.3765 (2)	0.8932 (2)	0.0110 (4)	0.5
N1B2	−0.0628 (2)	0.52312 (19)	0.89048 (18)	0.0116 (4)	0.5
C2B	−0.0399 (2)	0.6533 (2)	1.0542 (2)	0.0110 (4)	0.5
C3B	0.0431 (2)	0.5817 (2)	1.1512 (2)	0.0103 (4)	0.5
H3B	0.082 (3)	0.633 (3)	1.275 (3)	0.013 (6)*	0.5
H2B	−0.072 (3)	0.771 (3)	1.067 (3)	0.015 (6)*	0.5
H1B2	−0.125 (3)	0.539 (3)	0.794 (3)	0.008 (5)*	0.5
H1B1	0.126 (4)	0.327 (4)	1.087 (4)	0.040 (9)*	0.5
H1B	0.004 (3)	0.265 (3)	0.795 (3)	0.015 (6)*	0.5
H4	0.0000	0.0000	0.5000	0.049 (7)*
H21	0.4995 (19)	0.2841 (17)	0.5068 (15)	0.025 (3)*
H22	0.4530 (18)	0.0887 (16)	0.3585 (14)	0.020 (3)*
H1A1	0.2645 (19)	0.5485 (17)	0.5985 (15)	0.024 (3)*
H1A	0.1537 (18)	0.8421 (16)	0.7318 (14)	0.018 (3)*
H1A2	0.280 (3)	0.968 (2)	1.030 (2)	0.055 (5)*
H2A	0.4734 (18)	0.7595 (15)	1.0986 (14)	0.016 (3)*
H3A	0.4537 (18)	0.4759 (16)	0.8074 (14)	0.021 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0122 (2)	0.0083 (2)	0.0143 (3)	0.0021 (2)	0.0016 (2)	0.00145 (19)
O2	0.0139 (3)	0.0104 (2)	0.0115 (3)	0.0030 (2)	0.0012 (2)	0.00221 (19)
O3	0.0151 (3)	0.0141 (2)	0.0140 (3)	−0.0014 (2)	−0.0009 (2)	0.0052 (2)
O4	0.0112 (3)	0.0178 (2)	0.0153 (3)	−0.0036 (2)	−0.0009 (2)	0.00847 (19)
C1	0.0076 (3)	0.0094 (3)	0.0129 (3)	−0.0009 (3)	0.0021 (2)	0.0044 (2)
C2	0.0076 (3)	0.0124 (3)	0.0167 (4)	0.0005 (3)	0.0005 (3)	0.0068 (3)
C3	0.0101 (3)	0.0082 (3)	0.0140 (4)	0.0020 (3)	0.0005 (3)	0.0037 (2)
N1A1	0.0101 (3)	0.0093 (3)	0.0114 (3)	0.0009 (2)	0.0011 (2)	0.0017 (2)
C1A	0.0089 (3)	0.0095 (3)	0.0137 (3)	0.0005 (3)	0.0024 (2)	0.0049 (2)
N1A2	0.0095 (3)	0.0097 (3)	0.0139 (3)	0.0017 (2)	0.0013 (2)	0.0034 (2)
C2A	0.0107 (3)	0.0116 (3)	0.0137 (3)	0.0005 (3)	0.0004 (3)	0.0055 (2)
C3A	0.0108 (3)	0.0109 (3)	0.0172 (4)	0.0016 (3)	0.0014 (3)	0.0057 (3)
N1B1	0.0086 (6)	0.0103 (5)	0.0103 (6)	−0.0017 (5)	−0.0024 (4)	0.0046 (4)
C1B	0.0116 (7)	0.0107 (5)	0.0121 (7)	0.0064 (5)	−0.0001 (5)	0.0079 (5)
N1B2	0.0142 (6)	0.0092 (5)	0.0091 (6)	−0.0011 (5)	−0.0023 (5)	0.0045 (4)
C2B	0.0072 (6)	0.0103 (6)	0.0143 (7)	0.0017 (5)	−0.0018 (5)	0.0064 (5)
C3B	0.0088 (6)	0.0074 (5)	0.0129 (7)	0.0005 (5)	0.0030 (5)	0.0031 (5)

Geometric parameters (Å, º)

O1—C1	1.2478 (10)	N1B1—H1B1	0.95 (4)
O2—C1	1.2541 (10)	C1B—C2B^i	0.653 (3)
O3—C3	1.2307 (13)	C1B—C3B^i	0.691 (3)
O4—C3	1.2997 (10)	C1B—N1B2	1.320 (2)
O4—H4	1.2482 (8)	C1B—N1B1^i	1.730 (2)
C1—C2	1.5229 (14)	C1B—N1B2^i	1.745 (2)
C2—C3	1.5462 (15)	C1B—H1B	0.96 (2)
C2—H21	0.977 (11)	N1B2—N1B1^i	0.5940 (18)
C2—H22	0.974 (12)	N1B2—C3B^i	0.805 (2)
N1A1—C1A	1.3125 (11)	N1B2—C2B	1.383 (2)
N1A1—C3A	1.3800 (14)	N1B2—C1B^i	1.745 (2)
N1A1—H1A1	0.965 (12)	N1B2—C2B^i	1.870 (3)
C1A—N1A2	1.3278 (12)	N1B2—H1B2	0.98 (2)
C1A—H1A	0.944 (14)	C2B—C1B^i	0.653 (3)
N1A2—C2A	1.3739 (13)	C2B—N1B1^i	0.843 (2)
N1A2—H1A2	0.913 (16)	C2B—C3B	1.338 (3)
C2A—C3A	1.3423 (12)	C2B—N1B2^i	1.870 (3)
C2A—H2A	0.973 (12)	C2B—C3B^i	2.013 (2)
C3A—H3A	0.955 (13)	C2B—H2B	0.97 (3)
N1B1—N1B2^i	0.5940 (18)	C3B—C1B^i	0.691 (3)
N1B1—C2B^i	0.843 (2)	C3B—N1B2^i	0.805 (2)
N1B1—C1B	1.334 (3)	C3B—N1B1^i	1.915 (3)
N1B1—C3B	1.352 (2)	C3B—C2B^i	2.013 (2)
N1B1—C1B^i	1.730 (2)	C3B—H3B	1.00 (2)
N1B1—C3B^i	1.915 (3)
C3—O4—H4	111.45 (7)	N1B1—C1B—H1B	126.7 (17)
O1—C1—O2	121.87 (9)	N1B1^i—C1B—H1B	139.9 (16)
O1—C1—C2	117.35 (7)	N1B2^i—C1B—H1B	142.8 (17)
O2—C1—C2	120.78 (7)	N1B1^i—N1B2—C3B^i	149.9 (4)
C1—C2—C3	113.24 (7)	N1B1^i—N1B2—C1B	125.0 (3)
C1—C2—H21	110.3 (9)	C3B^i—N1B2—C1B	25.81 (16)
C3—C2—H21	110.2 (9)	N1B1^i—N1B2—C2B	18.8 (2)
C1—C2—H22	110.8 (8)	C3B^i—N1B2—C2B	132.1 (2)
C3—C2—H22	105.8 (9)	C1B—N1B2—C2B	106.58 (16)
H21—C2—H22	106.2 (10)	N1B1^i—N1B2—C1B^i	38.7 (2)
O3—C3—O4	123.99 (10)	C3B^i—N1B2—C1B^i	112.0 (2)
O3—C3—C2	120.79 (8)	C1B—N1B2—C1B^i	86.46 (13)
O4—C3—C2	115.20 (8)	C2B—N1B2—C1B^i	20.14 (10)
C1A—N1A1—C3A	108.30 (7)	N1B1^i—N1B2—C2B^i	112.1 (3)
C1A—N1A1—H1A1	124.3 (9)	C3B^i—N1B2—C2B^i	38.53 (17)
C3A—N1A1—H1A1	127.3 (9)	C1B—N1B2—C2B^i	12.89 (9)
N1A1—C1A—N1A2	108.33 (9)	C2B—N1B2—C2B^i	93.72 (13)
N1A1—C1A—H1A	124.6 (7)	C1B^i—N1B2—C2B^i	73.59 (10)
N1A2—C1A—H1A	127.1 (7)	N1B1^i—N1B2—H1B2	106.2 (12)
C1A—N1A2—C2A	109.67 (7)	C3B^i—N1B2—H1B2	102.7 (12)
C1A—N1A2—H1A2	125.8 (12)	C1B—N1B2—H1B2	128.5 (12)
C2A—N1A2—H1A2	124.5 (12)	C2B—N1B2—H1B2	124.9 (12)
C3A—C2A—N1A2	105.63 (9)	C1B^i—N1B2—H1B2	144.9 (12)
C3A—C2A—H2A	131.3 (7)	C2B^i—N1B2—H1B2	141.2 (12)
N1A2—C2A—H2A	123.1 (7)	C1B^i—C2B—N1B1^i	125.7 (3)
C2A—C3A—N1A1	108.07 (8)	C1B^i—C2B—C3B	5.72 (19)
C2A—C3A—H3A	132.9 (8)	N1B1^i—C2B—C3B	121.1 (2)
N1A1—C3A—H3A	119.0 (7)	C1B^i—C2B—N1B2	113.0 (2)
N1B2^i—N1B1—C2B^i	148.0 (3)	N1B1^i—C2B—N1B2	13.16 (14)
N1B2^i—N1B1—C1B	125.2 (3)	C3B—C2B—N1B2	108.23 (15)
C2B^i—N1B1—C1B	23.43 (16)	C1B^i—C2B—N1B2^i	26.80 (17)
N1B2^i—N1B1—C3B	17.4 (2)	N1B1^i—C2B—N1B2^i	99.10 (18)
C2B^i—N1B1—C3B	131.7 (2)	C3B—C2B—N1B2^i	22.00 (8)
C1B—N1B1—C3B	108.41 (16)	N1B2—C2B—N1B2^i	86.28 (13)
N1B2^i—N1B1—C1B^i	38.7 (2)	C1B^i—C2B—C3B^i	95.8 (2)
C2B^i—N1B1—C1B^i	109.9 (2)	N1B1^i—C2B—C3B^i	30.09 (15)
C1B—N1B1—C1B^i	86.65 (12)	C3B—C2B—C3B^i	91.05 (12)
C3B—N1B1—C1B^i	21.79 (10)	N1B2—C2B—C3B^i	17.24 (10)
N1B2^i—N1B1—C3B^i	111.7 (3)	N1B2^i—C2B—C3B^i	69.07 (9)
C2B^i—N1B1—C3B^i	36.75 (16)	C1B^i—C2B—H2B	133.3 (14)
C1B—N1B1—C3B^i	13.47 (9)	N1B1^i—C2B—H2B	101.0 (14)
C3B—N1B1—C3B^i	94.98 (13)	C3B—C2B—H2B	137.7 (13)
C1B^i—N1B1—C3B^i	73.21 (10)	N1B2—C2B—H2B	113.6 (14)
N1B2^i—N1B1—H1B1	107.7 (16)	N1B2^i—C2B—H2B	159.5 (13)
C2B^i—N1B1—H1B1	103.6 (16)	C3B^i—C2B—H2B	130.8 (14)
C1B—N1B1—H1B1	127.0 (16)	C1B^i—C3B—N1B2^i	123.7 (3)
C3B—N1B1—H1B1	124.6 (16)	C1B^i—C3B—C2B	5.41 (18)
C1B^i—N1B1—H1B1	146.4 (16)	N1B2^i—C3B—C2B	119.5 (2)
C3B^i—N1B1—H1B1	140.4 (16)	C1B^i—C3B—N1B1	111.7 (2)
C2B^i—C1B—C3B^i	168.9 (4)	N1B2^i—C3B—N1B1	12.74 (16)
C2B^i—C1B—N1B2	140.3 (2)	C2B—C3B—N1B1	107.15 (15)
C3B^i—C1B—N1B2	30.46 (16)	C1B^i—C3B—N1B1^i	26.73 (16)
C2B^i—C1B—N1B1	30.88 (17)	N1B2^i—C3B—N1B1^i	97.31 (19)
C3B^i—C1B—N1B1	139.8 (2)	C2B—C3B—N1B1^i	22.15 (8)
N1B2—C1B—N1B1	109.62 (14)	N1B1—C3B—N1B1^i	85.02 (13)
C2B^i—C1B—N1B1^i	124.0 (2)	C1B^i—C3B—C2B^i	93.4 (2)
C3B^i—C1B—N1B1^i	46.56 (17)	N1B2^i—C3B—C2B^i	30.62 (16)
N1B2—C1B—N1B1^i	16.34 (9)	C2B—C3B—C2B^i	88.95 (12)
N1B1—C1B—N1B1^i	93.35 (12)	N1B1—C3B—C2B^i	18.22 (10)
C2B^i—C1B—N1B2^i	46.84 (18)	N1B1^i—C3B—C2B^i	66.80 (9)
C3B^i—C1B—N1B2^i	123.7 (2)	C1B^i—C3B—H3B	127.1 (15)
N1B2—C1B—N1B2^i	93.54 (13)	N1B2^i—C3B—H3B	108.8 (15)
N1B1—C1B—N1B2^i	16.15 (8)	C2B—C3B—H3B	131.7 (14)
N1B1^i—C1B—N1B2^i	77.23 (10)	N1B1—C3B—H3B	121.2 (14)
C2B^i—C1B—H1B	95.9 (17)	N1B1^i—C3B—H3B	153.8 (14)
C3B^i—C1B—H1B	93.4 (17)	C2B^i—C3B—H3B	139.4 (14)
N1B2—C1B—H1B	123.7 (17)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^ii	1.25 (1)	2.45 (1)	3.1813 (12)	115 (1)
C2—H21···O1^iii	0.977 (11)	2.782 (13)	3.6741 (14)	152.2 (12)
C2—H22···O3^iv	0.974 (12)	2.437 (13)	3.3036 (13)	148.1 (11)
N1A1—H1A1···O1	0.965 (12)	1.702 (12)	2.6658 (11)	176.4 (14)
C1A—H1A···O4^v	0.944 (14)	2.393 (14)	3.3275 (14)	170.6 (10)
N1A2—H1A2···O2^vi	0.913 (16)	1.707 (16)	2.6165 (10)	173.7 (16)
C2A—H2A···O3^vii	0.973 (12)	2.201 (11)	3.1606 (14)	168.9 (11)
C3A—H3A···O3	0.955 (13)	2.483 (12)	3.2672 (12)	139.3 (9)
C3B—H3B···O1^viii	1.00 (2)	2.52 (3)	3.112 (2)	117.1 (16)
C2B—H2B···O2^v	0.97 (3)	2.42 (3)	3.066 (2)	123.7 (15)
C2B—H2B···O4^vi	0.97 (3)	3.052 (19)	3.5045 (17)	110.0 (16)
N1B2—H1B2···O1^v	0.98 (2)	1.85 (2)	2.833 (2)	175 (2)
N1B2—H1B2···O2^v	0.98 (2)	2.37 (2)	2.9682 (19)	118.8 (14)
N1B1—H1B1···O1^viii	0.95 (4)	2.48 (3)	3.0546 (19)	119 (2)
N1B1—H1B1···O2^viii	0.95 (4)	1.80 (4)	2.744 (2)	176 (3)
C1B—H1B···O3	0.96 (2)	2.83 (2)	3.471 (2)	124.9 (17)
C1B—H1B···O4^ii	0.96 (2)	2.52 (2)	3.4392 (17)	160 (2)

Symmetry codes: (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z+1; (vi) x, y+1, z+1; (vii) −x+1, −y+1, −z+2; (viii) x, y, z+1.

(m120)

Crystal data

C6H5O8·3(C3H5N2)	Z = 2
Mr = 206.18	F(000) = 216
Triclinic, P1	Dx = 1.450 Mg m^−3
a = 6.999 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.378 (2) Å	Cell parameters from 4533 reflections
c = 9.249 (2) Å	θ = 4–56.1°
α = 116.22 (3)°	µ = 0.12 mm^−1
β = 101.88 (3)°	T = 120 K
γ = 91.18 (3)°	Unshaped, colorless
V = 472.3 (2) Å^3	0.34 × 0.32 × 0.21 mm

Data collection

Xcalibur-Oxford Diffraction diffractometer	1657 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
CCD scans	θmax = 28.0°, θmin = 2.8°
Absorption correction: numerical CrysAlis v171.33.42	h = −9→8
Tmin = 0.955, Tmax = 1.120	k = −11→11
4533 measured reflections	l = −11→11
2104 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0322P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.075	(Δ/σ)max = 0.069
S = 1.27	Δρmax = 0.28 e Å^−3
2104 reflections	Δρmin = −0.22 e Å^−3
204 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.038 (3)

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.22235 (6)	0.42389 (4)	0.38854 (4)	0.02189 (11)
O2	0.21580 (6)	0.17148 (5)	0.16269 (4)	0.02253 (11)
O3	0.33428 (6)	0.14745 (5)	0.65179 (4)	0.02743 (11)
O4	0.08703 (6)	0.05841 (5)	0.42726 (4)	0.02960 (11)
C1	0.26718 (8)	0.26692 (6)	0.31731 (6)	0.01624 (13)
C2	0.38750 (8)	0.19316 (7)	0.42511 (6)	0.02025 (14)
C3	0.26421 (8)	0.13092 (6)	0.51255 (6)	0.01868 (14)
N1A1	0.29114 (7)	0.62721 (5)	0.71723 (5)	0.01849 (12)
C1A	0.23165 (8)	0.78764 (6)	0.78811 (6)	0.01830 (14)
N1A2	0.29938 (7)	0.85690 (5)	0.95114 (5)	0.01834 (12)
C2A	0.40577 (8)	0.73638 (7)	0.98651 (6)	0.02086 (14)
C3A	0.40032 (8)	0.59334 (7)	0.84027 (6)	0.02058 (15)
N1B1	0.07094 (13)	0.40792 (10)	1.04915 (10)	0.0197 (2)	0.5
C1B	0.00446 (17)	0.37792 (12)	0.89213 (12)	0.0192 (3)	0.5
N1B2	−0.06134 (13)	0.52466 (10)	0.89293 (10)	0.0173 (2)	0.5
C2B	−0.03820 (17)	0.65449 (13)	1.05496 (12)	0.0197 (3)	0.5
C3B	0.04367 (17)	0.58037 (12)	1.15121 (12)	0.0191 (3)	0.5
H3B	0.0755 (17)	0.6307 (13)	1.2713 (12)	0.018 (3)*	0.5
H2B	−0.0765 (16)	0.7624 (13)	1.0744 (12)	0.017 (3)*	0.5
H1B2	−0.1209 (19)	0.5277 (16)	0.7917 (14)	0.041 (4)*	0.5
H1B1	0.123 (2)	0.3221 (15)	1.0825 (15)	0.046 (4)*	0.5
H1B	0.0135 (17)	0.2716 (15)	0.7990 (14)	0.032 (4)*	0.5
H1A1	0.2665 (9)	0.5508 (8)	0.6007 (7)	0.0385 (19)*
H1A	0.1513 (9)	0.8425 (7)	0.7304 (7)	0.0280 (17)*
H1A2	0.2749 (9)	0.9647 (8)	1.0304 (7)	0.0360 (18)*
H2A	0.4663 (9)	0.7641 (7)	1.0975 (7)	0.0267 (16)*
H3A	0.4520 (9)	0.4852 (7)	0.8159 (7)	0.0297 (17)*
H4	0.0000	0.0000	0.5000	0.101 (5)*
H21	0.4932 (8)	0.2817 (7)	0.5054 (7)	0.0248 (16)*
H22	0.4435 (8)	0.0882 (7)	0.3563 (6)	0.0248 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0302 (2)	0.01590 (14)	0.01657 (15)	0.00613 (15)	0.00415 (15)	0.00527 (11)
O2	0.0317 (2)	0.01995 (15)	0.01319 (14)	0.00705 (15)	0.00393 (14)	0.00565 (11)
O3	0.0330 (2)	0.03204 (16)	0.01615 (15)	0.00080 (17)	−0.00064 (16)	0.01299 (11)
O4	0.0269 (2)	0.04083 (16)	0.02477 (16)	−0.00979 (16)	−0.00412 (15)	0.02315 (11)
C1	0.0170 (2)	0.01767 (19)	0.01550 (19)	0.00053 (19)	0.00485 (18)	0.00852 (13)
C2	0.0195 (3)	0.0225 (2)	0.0183 (2)	0.0032 (2)	0.0012 (2)	0.01034 (15)
C3	0.0251 (3)	0.01442 (19)	0.0161 (2)	0.0054 (2)	0.0017 (2)	0.00776 (14)
N1A1	0.0219 (2)	0.01732 (17)	0.01364 (17)	0.00221 (17)	0.00327 (16)	0.00523 (12)
C1A	0.0182 (3)	0.0188 (2)	0.0172 (2)	0.0016 (2)	0.00333 (19)	0.00794 (14)
N1A2	0.0218 (2)	0.01581 (17)	0.01434 (17)	0.00274 (17)	0.00396 (17)	0.00430 (12)
C2A	0.0224 (3)	0.0219 (2)	0.0185 (2)	0.0020 (2)	0.0022 (2)	0.01045 (14)
C3A	0.0224 (3)	0.0197 (2)	0.0197 (2)	0.0046 (2)	0.0042 (2)	0.00926 (15)
N1B1	0.0229 (5)	0.0151 (3)	0.0236 (4)	0.0061 (3)	0.0064 (3)	0.0105 (2)
C1B	0.0277 (6)	0.0170 (4)	0.0204 (4)	0.0082 (4)	0.0043 (4)	0.0154 (3)
N1B2	0.0210 (5)	0.0162 (3)	0.0189 (3)	0.0063 (3)	0.0036 (3)	0.0120 (2)
C2B	0.0258 (6)	0.0160 (4)	0.0190 (4)	0.0081 (4)	0.0054 (4)	0.0093 (3)
C3B	0.0267 (6)	0.0180 (4)	0.0191 (4)	0.0074 (4)	0.0059 (4)	0.0139 (3)

Geometric parameters (Å, º)

O1—C1	1.2643 (7)	N1B1—C3B^i	1.9076 (16)
O2—C1	1.2569 (8)	N1B1—H1B1	0.952 (14)
O3—C3	1.2239 (8)	C1B—C2B^i	0.6644 (15)
O4—C3	1.2930 (8)	C1B—C3B^i	0.6850 (15)
O4—H4	1.2290 (5)	C1B—N1B2	1.3192 (14)
C1—C2	1.5184 (9)	C1B—N1B2^i	1.7331 (14)
C2—C3	1.5205 (10)	C1B—N1B1^i	1.7574 (14)
C2—H21	0.956 (5)	C1B—H1B	0.941 (10)
C2—H22	0.977 (5)	N1B2—N1B1^i	0.5996 (11)
N1A1—C1A	1.3291 (8)	N1B2—C3B^i	0.8150 (12)
N1A1—C3A	1.3768 (9)	N1B2—C2B	1.3812 (13)
N1A1—H1A1	0.954 (6)	N1B2—C1B^i	1.7331 (14)
C1A—N1A2	1.3252 (8)	N1B2—C2B^i	1.8747 (16)
C1A—H1A	0.957 (7)	N1B2—H1B2	0.955 (13)
N1A2—C2A	1.3797 (8)	C2B—C1B^i	0.6645 (15)
N1A2—H1A2	0.925 (6)	C2B—N1B1^i	0.8440 (13)
C2A—C3A	1.3460 (9)	C2B—C3B	1.3414 (17)
C2A—H2A	0.945 (6)	C2B—N1B2^i	1.8747 (16)
C3A—H3A	0.932 (6)	C2B—H2B	0.899 (11)
N1B1—N1B2^i	0.5996 (11)	C3B—C1B^i	0.6850 (15)
N1B1—C2B^i	0.8441 (13)	C3B—N1B2^i	0.8150 (12)
N1B1—C1B	1.3354 (14)	C3B—N1B1^i	1.9076 (16)
N1B1—C3B	1.3767 (13)	C3B—H3B	0.970 (10)
N1B1—C1B^i	1.7574 (14)
C3—O4—H4	111.59 (4)	N1B2—C1B—N1B1^i	15.44 (5)
O2—C1—O1	122.60 (6)	N1B1—C1B—N1B1^i	93.08 (8)
O2—C1—C2	119.57 (5)	N1B2^i—C1B—N1B1^i	76.17 (6)
O1—C1—C2	117.83 (5)	C2B^i—C1B—H1B	93.2 (9)
C1—C2—C3	112.60 (5)	C3B^i—C1B—H1B	96.5 (8)
C1—C2—H21	110.0 (4)	N1B2—C1B—H1B	127.2 (8)
C3—C2—H21	109.6 (4)	N1B1—C1B—H1B	124.2 (8)
C1—C2—H22	109.8 (4)	N1B2^i—C1B—H1B	141.1 (8)
C3—C2—H22	106.3 (4)	N1B1^i—C1B—H1B	142.7 (8)
H21—C2—H22	108.3 (5)	N1B1^i—N1B2—C3B^i	153.1 (2)
O3—C3—O4	124.49 (6)	N1B1^i—N1B2—C1B	128.69 (17)
O3—C3—C2	120.63 (5)	C3B^i—N1B2—C1B	25.84 (9)
O4—C3—C2	114.86 (5)	N1B1^i—N1B2—C2B	20.17 (12)
C1A—N1A1—C3A	108.36 (5)	C3B^i—N1B2—C2B	134.90 (13)
C1A—N1A1—H1A1	125.7 (4)	C1B—N1B2—C2B	109.37 (9)
C3A—N1A1—H1A1	125.9 (4)	N1B1^i—N1B2—C1B^i	40.52 (13)
N1A2—C1A—N1A1	108.70 (6)	C3B^i—N1B2—C1B^i	113.91 (12)
N1A2—C1A—H1A	126.0 (3)	C1B—N1B2—C1B^i	88.44 (8)
N1A1—C1A—H1A	125.3 (3)	C2B—N1B2—C1B^i	20.99 (6)
C1A—N1A2—C2A	108.73 (5)	N1B1^i—N1B2—C2B^i	115.38 (15)
C1A—N1A2—H1A2	126.7 (4)	C3B^i—N1B2—C2B^i	38.87 (9)
C2A—N1A2—H1A2	124.4 (4)	C1B—N1B2—C2B^i	13.31 (5)
C3A—C2A—N1A2	106.79 (6)	C2B—N1B2—C2B^i	96.14 (8)
C3A—C2A—H2A	132.8 (4)	C1B^i—N1B2—C2B^i	75.18 (6)
N1A2—C2A—H2A	120.4 (4)	N1B1^i—N1B2—H1B2	109.8 (7)
C2A—C3A—N1A1	107.43 (6)	C3B^i—N1B2—H1B2	95.2 (7)
C2A—C3A—H3A	131.0 (4)	C1B—N1B2—H1B2	120.9 (7)
N1A1—C3A—H3A	121.5 (4)	C2B—N1B2—H1B2	129.6 (7)
N1B2^i—N1B1—C2B^i	145.6 (2)	C1B^i—N1B2—H1B2	150.3 (7)
N1B2^i—N1B1—C1B	122.52 (17)	C2B^i—N1B2—H1B2	134.0 (7)
C2B^i—N1B1—C1B	24.32 (9)	C1B^i—C2B—N1B1^i	124.13 (17)
N1B2^i—N1B1—C3B	15.52 (13)	C1B^i—C2B—C3B	6.34 (13)
C2B^i—N1B1—C3B	131.92 (14)	N1B1^i—C2B—C3B	119.85 (13)
C1B—N1B1—C3B	107.97 (9)	C1B^i—C2B—N1B2	110.90 (14)
N1B2^i—N1B1—C1B^i	35.86 (13)	N1B1^i—C2B—N1B2	14.18 (8)
C2B^i—N1B1—C1B^i	110.83 (12)	C3B—C2B—N1B2	106.22 (9)
C1B—N1B1—C1B^i	86.92 (8)	C1B^i—C2B—N1B2^i	27.20 (10)
C3B—N1B1—C1B^i	21.09 (6)	N1B1^i—C2B—N1B2^i	97.44 (11)
N1B2^i—N1B1—C3B^i	108.97 (15)	C3B—C2B—N1B2^i	22.41 (5)
C2B^i—N1B1—C3B^i	37.58 (10)	N1B2—C2B—N1B2^i	83.86 (8)
C1B—N1B1—C3B^i	13.55 (5)	C1B^i—C2B—H2B	129.8 (7)
C3B—N1B1—C3B^i	94.48 (8)	N1B1^i—C2B—H2B	105.4 (7)
C1B^i—N1B1—C3B^i	73.41 (6)	C3B—C2B—H2B	134.7 (7)
N1B2^i—N1B1—H1B1	112.0 (7)	N1B2—C2B—H2B	119.1 (7)
C2B^i—N1B1—H1B1	100.9 (7)	N1B2^i—C2B—H2B	157.0 (7)
C1B—N1B1—H1B1	125.1 (7)	C1B^i—C3B—N1B2^i	122.92 (16)
C3B—N1B1—H1B1	126.9 (7)	C1B^i—C3B—C2B	6.14 (12)
C1B^i—N1B1—H1B1	147.8 (7)	N1B2^i—C3B—C2B	118.72 (12)
C3B^i—N1B1—H1B1	138.5 (7)	C1B^i—C3B—N1B1	112.57 (13)
C2B^i—C1B—C3B^i	167.5 (2)	N1B2^i—C3B—N1B1	11.36 (9)
C2B^i—C1B—N1B2	139.49 (15)	C2B—C3B—N1B1	108.02 (9)
C3B^i—C1B—N1B2	31.24 (9)	C1B^i—C3B—N1B1^i	27.17 (10)
C2B^i—C1B—N1B1	31.55 (10)	N1B2^i—C3B—N1B1^i	96.16 (11)
C3B^i—C1B—N1B1	139.28 (14)	C2B—C3B—N1B1^i	22.57 (5)
N1B2—C1B—N1B1	108.42 (8)	N1B1—C3B—N1B1^i	85.52 (8)
C2B^i—C1B—N1B2^i	48.12 (11)	C1B^i—C3B—H3B	124.2 (7)
C3B^i—C1B—N1B2^i	122.32 (13)	N1B2^i—C3B—H3B	111.9 (7)
N1B2—C1B—N1B2^i	91.56 (8)	C2B—C3B—H3B	129.0 (7)
N1B1—C1B—N1B2^i	16.96 (5)	N1B1—C3B—H3B	122.9 (7)
C2B^i—C1B—N1B1^i	124.05 (13)	N1B1^i—C3B—H3B	151.3 (7)
C3B^i—C1B—N1B1^i	46.34 (10)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^ii	1.23 (1)	2.44 (1)	3.1611 (12)	115 (1)
O4—H4···O4^ii	1.23 (1)	1.23 (1)	2.4580 (11)	180
C2—H21···O1^iii	0.956 (5)	2.805 (6)	3.6791 (18)	152.5 (5)
C2—H22···O3^iv	0.977 (5)	2.523 (6)	3.3833 (13)	146.8 (5)
N1A1—H1A1···O1	0.954 (6)	1.723 (6)	2.6764 (12)	176.7 (7)
C1A—H1A···O4^v	0.957 (7)	2.393 (7)	3.3416 (12)	171.3 (5)
N1A2—H1A2···O2^vi	0.925 (6)	1.742 (6)	2.6637 (12)	174.1 (6)
C2A—H2A···O3^vii	0.945 (6)	2.232 (6)	3.1611 (14)	167.5 (6)
C3A—H3A···O3	0.932 (6)	2.566 (5)	3.3242 (14)	138.8 (4)
C3B—H3B···O1^viii	0.970 (10)	2.551 (12)	3.0954 (15)	115.5 (8)
C2B—H2B···O2^v	0.899 (11)	2.506 (12)	3.0596 (15)	120.3 (7)
C2B—H2B···O4^vi	0.899 (11)	3.050 (9)	3.524 (2)	114.8 (8)
N1B2—H1B2···O1^v	0.96 (1)	1.89 (1)	2.8349 (13)	170 (1)
N1B2—H1B2···O2^v	0.96 (1)	2.49 (1)	2.9925 (13)	113 (1)
N1B1—H1B1···O1^viii	0.95 (1)	2.50 (1)	3.0410 (13)	116 (1)
N1B1—H1B1···O2^viii	0.95 (1)	1.80 (1)	2.7453 (13)	175 (1)
C1B—H1B···O3	0.941 (10)	2.842 (12)	3.5358 (17)	131.4 (9)
C1B—H1B···O4^ii	0.941 (10)	2.592 (10)	3.4760 (19)	156.5 (11)

Symmetry codes: (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z+1; (vi) x, y+1, z+1; (vii) −x+1, −y+1, −z+2; (viii) x, y, z+1.

(m295)

Crystal data

C6H5O8·3(C3H5N2)	Z = 2
Mr = 206.18	F(000) = 216
Triclinic, P1	Dx = 1.453 Mg m^−3
a = 6.980 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.400 (2) Å	Cell parameters from 3296 reflections
c = 9.230 (2) Å	θ = 4–56.1°
α = 116.40 (3)°	µ = 0.12 mm^−1
β = 101.57 (3)°	T = 295 K
γ = 91.09 (3)°	Unshaped, colorless
V = 471.3 (2) Å^3	0.34 × 0.32 × 0.21 mm

Data collection

Xcalibur-Oxford Diffraction diffractometer	1409 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
CCD scans	θmax = 28.5°, θmin = 3.5°
Absorption correction: numerical CrysAlis v171.33.42	h = −8→9
Tmin = 0.923, Tmax = 1.342	k = −11→11
3296 measured reflections	l = −12→9
2075 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0322P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.077	(Δ/σ)max = 0.020
S = 0.95	Δρmax = 0.21 e Å^−3
2075 reflections	Δρmin = −0.21 e Å^−3
204 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.040 (2)

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.22212 (8)	0.42410 (6)	0.38827 (6)	0.02018 (16)
O2	0.21602 (8)	0.17159 (6)	0.16260 (6)	0.02048 (16)
O3	0.33476 (9)	0.14770 (7)	0.65186 (6)	0.02495 (16)
O4	0.08683 (9)	0.05846 (7)	0.42720 (6)	0.02665 (16)
C1	0.26733 (11)	0.26707 (9)	0.31725 (8)	0.0155 (2)
C2	0.38797 (12)	0.19357 (10)	0.42455 (8)	0.0180 (2)
C3	0.26441 (12)	0.13113 (9)	0.51245 (9)	0.0177 (2)
N1A1	0.29157 (10)	0.62663 (8)	0.71732 (7)	0.01724 (18)
C1A	0.23138 (12)	0.78757 (10)	0.78761 (8)	0.0170 (2)
N1A2	0.29976 (9)	0.85671 (8)	0.95151 (7)	0.01723 (18)
C2A	0.40650 (12)	0.73568 (10)	0.98599 (9)	0.0190 (2)
C3A	0.40074 (12)	0.59229 (10)	0.83979 (8)	0.0189 (2)
N1B1	0.07017 (19)	0.40799 (15)	1.04968 (14)	0.0176 (4)	0.5
C1B	0.0044 (2)	0.37842 (18)	0.89125 (17)	0.0172 (4)	0.5
N1B2	−0.06198 (19)	0.52515 (15)	0.89252 (14)	0.0167 (4)	0.5
C2B	−0.0381 (2)	0.65397 (19)	1.05460 (17)	0.0185 (4)	0.5
C3B	0.0433 (2)	0.57945 (18)	1.15059 (17)	0.0169 (4)	0.5
H1A1	0.2673 (13)	0.5516 (11)	0.6025 (10)	0.045 (3)*
H1A	0.1507 (11)	0.8489 (9)	0.7294 (8)	0.023 (2)*
H1A2	0.2797 (13)	0.9704 (11)	1.0365 (10)	0.048 (3)*
H2A	0.4681 (11)	0.7614 (9)	1.0963 (8)	0.022 (2)*
H3A	0.4555 (11)	0.4870 (9)	0.8168 (8)	0.020 (2)*
H3B	0.080 (2)	0.6253 (18)	1.2761 (15)	0.016 (4)*	0.5
H2B	−0.073 (2)	0.753 (2)	1.0707 (17)	0.028 (5)*	0.5
H1B2	−0.116 (3)	0.535 (2)	0.7899 (17)	0.042 (5)*	0.5
H1B1	0.125 (3)	0.3191 (19)	1.0916 (18)	0.045 (6)*	0.5
H1B	0.008 (3)	0.273 (2)	0.790 (2)	0.058 (6)*	0.5
H4	0.0000	0.0000	0.5000	0.094 (6)*
H21	0.4913 (11)	0.2850 (9)	0.5048 (8)	0.022 (2)*
H22	0.4485 (11)	0.0872 (9)	0.3550 (8)	0.023 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0265 (3)	0.0155 (2)	0.0161 (2)	0.0061 (2)	0.0042 (2)	0.00515 (16)
O2	0.0279 (3)	0.0186 (2)	0.0117 (2)	0.0062 (2)	0.0031 (2)	0.00457 (16)
O3	0.0306 (3)	0.0298 (2)	0.0141 (2)	0.0011 (2)	−0.0009 (2)	0.01228 (17)
O4	0.0250 (3)	0.0369 (3)	0.0217 (2)	−0.0082 (2)	−0.0030 (2)	0.02050 (17)
C1	0.0148 (4)	0.0172 (3)	0.0163 (3)	0.0006 (3)	0.0052 (3)	0.0087 (2)
C2	0.0175 (4)	0.0191 (3)	0.0169 (3)	0.0025 (3)	0.0013 (3)	0.0090 (2)
C3	0.0230 (4)	0.0124 (3)	0.0168 (3)	0.0046 (3)	0.0020 (3)	0.0069 (2)
N1A1	0.0213 (3)	0.0158 (3)	0.0123 (2)	0.0029 (3)	0.0028 (2)	0.00483 (19)
C1A	0.0174 (4)	0.0179 (3)	0.0160 (3)	0.0013 (3)	0.0034 (3)	0.0082 (2)
N1A2	0.0190 (3)	0.0156 (3)	0.0143 (2)	0.0023 (3)	0.0036 (2)	0.0045 (2)
C2A	0.0201 (4)	0.0207 (3)	0.0161 (3)	0.0020 (3)	0.0021 (3)	0.0093 (2)
C3A	0.0210 (4)	0.0177 (3)	0.0177 (3)	0.0045 (3)	0.0031 (3)	0.0084 (2)
N1B1	0.0220 (7)	0.0144 (5)	0.0197 (5)	0.0063 (5)	0.0069 (5)	0.0096 (4)
C1B	0.0244 (9)	0.0143 (6)	0.0187 (6)	0.0076 (6)	0.0040 (6)	0.0129 (4)
N1B2	0.0210 (7)	0.0153 (5)	0.0180 (5)	0.0081 (5)	0.0046 (5)	0.0112 (4)
C2B	0.0235 (8)	0.0140 (6)	0.0189 (6)	0.0065 (6)	0.0057 (6)	0.0078 (5)
C3B	0.0222 (8)	0.0168 (6)	0.0180 (6)	0.0084 (6)	0.0044 (6)	0.0134 (4)

Geometric parameters (Å, º)

O1—C1	1.2645 (10)	N1B1—H1B1	1.030 (17)
O2—C1	1.2549 (9)	C1B—C2B^i	0.675 (2)
O3—C3	1.2251 (10)	C1B—C3B^i	0.678 (2)
O4—C3	1.2965 (11)	C1B—N1B2	1.321 (2)
O4—H4	1.2269 (7)	C1B—N1B2^i	1.7405 (19)
C1—C2	1.5166 (12)	C1B—N1B1^i	1.751 (2)
C2—C3	1.5229 (13)	C1B—H1B	0.969 (16)
C2—H21	0.958 (6)	N1B2—N1B1^i	0.5919 (15)
C2—H22	1.001 (7)	N1B2—C3B^i	0.8134 (18)
N1A1—C1A	1.3326 (11)	N1B2—C2B	1.3749 (18)
N1A1—C3A	1.3764 (11)	N1B2—C1B^i	1.7404 (19)
N1A1—H1A1	0.938 (8)	N1B2—C2B^i	1.883 (2)
C1A—N1A2	1.3312 (10)	N1B2—H1B2	0.985 (16)
C1A—H1A	1.003 (8)	C2B—C1B^i	0.675 (2)
N1A2—C2A	1.3826 (11)	C2B—N1B1^i	0.8432 (17)
N1A2—H1A2	0.964 (8)	C2B—C3B	1.343 (2)
C2A—C3A	1.3433 (11)	C2B—N1B2^i	1.883 (2)
C2A—H2A	0.945 (7)	C2B—C3B^i	2.025 (2)
C3A—H3A	0.923 (7)	C2B—H2B	0.825 (16)
N1B1—N1B2^i	0.5920 (15)	C3B—C1B^i	0.678 (2)
N1B1—C2B^i	0.8432 (17)	C3B—N1B2^i	0.8134 (18)
N1B1—C1B	1.347 (2)	C3B—N1B1^i	1.909 (2)
N1B1—C3B	1.3655 (18)	C3B—C2B^i	2.025 (2)
N1B1—C1B^i	1.751 (2)	C3B—H3B	1.018 (13)
N1B1—C3B^i	1.909 (2)
C3—O4—H4	111.61 (6)	N1B1—C1B—H1B	128.6 (13)
O2—C1—O1	122.34 (8)	N1B2^i—C1B—H1B	145.2 (13)
O2—C1—C2	119.52 (7)	N1B1^i—C1B—H1B	138.1 (13)
O1—C1—C2	118.14 (6)	N1B1^i—N1B2—C3B^i	152.3 (3)
C1—C2—C3	112.59 (7)	N1B1^i—N1B2—C1B	128.4 (2)
C1—C2—H21	108.5 (5)	C3B^i—N1B2—C1B	25.04 (13)
C3—C2—H21	109.9 (5)	N1B1^i—N1B2—C2B	19.99 (18)
C1—C2—H22	110.5 (4)	C3B^i—N1B2—C2B	133.80 (19)
C3—C2—H22	106.6 (5)	C1B—N1B2—C2B	109.04 (13)
H21—C2—H22	108.7 (6)	N1B1^i—N1B2—C1B^i	40.56 (18)
O3—C3—O4	124.59 (9)	C3B^i—N1B2—C1B^i	112.68 (17)
O3—C3—C2	120.51 (7)	C1B—N1B2—C1B^i	88.00 (11)
O4—C3—C2	114.89 (7)	C2B—N1B2—C1B^i	21.12 (9)
C1A—N1A1—C3A	109.05 (6)	N1B1^i—N1B2—C2B^i	114.8 (2)
C1A—N1A1—H1A1	125.0 (6)	C3B^i—N1B2—C2B^i	38.32 (13)
C3A—N1A1—H1A1	125.9 (6)	C1B—N1B2—C2B^i	13.59 (8)
N1A2—C1A—N1A1	107.96 (8)	C2B—N1B2—C2B^i	95.56 (11)
N1A2—C1A—H1A	125.0 (4)	C1B^i—N1B2—C2B^i	74.47 (9)
N1A1—C1A—H1A	127.0 (4)	N1B1^i—N1B2—H1B2	108.7 (9)
C1A—N1A2—C2A	108.79 (7)	C3B^i—N1B2—H1B2	97.9 (9)
C1A—N1A2—H1A2	128.0 (6)	C1B—N1B2—H1B2	122.7 (9)
C2A—N1A2—H1A2	123.2 (6)	C2B—N1B2—H1B2	128.2 (9)
C3A—C2A—N1A2	107.10 (7)	C1B^i—N1B2—H1B2	149.3 (9)
C3A—C2A—H2A	131.5 (5)	C2B^i—N1B2—H1B2	136.2 (9)
N1A2—C2A—H2A	121.4 (5)	C1B^i—C2B—N1B1^i	124.7 (2)
C2A—C3A—N1A1	107.10 (7)	C1B^i—C2B—C3B	6.82 (17)
C2A—C3A—H3A	130.3 (4)	N1B1^i—C2B—C3B	119.91 (19)
N1A1—C3A—H3A	122.6 (4)	C1B^i—C2B—N1B2	111.6 (2)
N1B2^i—N1B1—C2B^i	146.1 (3)	N1B1^i—C2B—N1B2	13.89 (12)
N1B2^i—N1B1—C1B	122.8 (2)	C3B—C2B—N1B2	106.46 (13)
C2B^i—N1B1—C1B	24.32 (14)	C1B^i—C2B—N1B2^i	27.39 (15)
N1B2^i—N1B1—C3B	16.07 (19)	N1B1^i—C2B—N1B2^i	97.86 (16)
C2B^i—N1B1—C3B	131.4 (2)	C3B—C2B—N1B2^i	22.05 (7)
C1B—N1B1—C3B	107.46 (13)	N1B2—C2B—N1B2^i	84.44 (11)
N1B2^i—N1B1—C1B^i	36.24 (19)	C1B^i—C2B—C3B^i	94.77 (18)
C2B^i—N1B1—C1B^i	110.67 (18)	N1B1^i—C2B—C3B^i	30.37 (13)
C1B—N1B1—C1B^i	86.75 (11)	C3B—C2B—C3B^i	89.64 (11)
C3B—N1B1—C1B^i	20.77 (8)	N1B2—C2B—C3B^i	16.85 (8)
N1B2^i—N1B1—C3B^i	109.3 (2)	N1B2^i—C2B—C3B^i	67.61 (8)
C2B^i—N1B1—C3B^i	37.58 (14)	C1B^i—C2B—H2B	130.6 (10)
C1B—N1B1—C3B^i	13.57 (8)	N1B1^i—C2B—H2B	104.1 (10)
C3B—N1B1—C3B^i	93.97 (11)	C3B—C2B—H2B	135.9 (10)
C1B^i—N1B1—C3B^i	73.23 (9)	N1B2—C2B—H2B	117.6 (10)
N1B2^i—N1B1—H1B1	108.7 (8)	N1B2^i—C2B—H2B	157.9 (10)
C2B^i—N1B1—H1B1	103.8 (8)	C3B^i—C2B—H2B	134.5 (10)
C1B—N1B1—H1B1	128.1 (8)	C1B^i—C3B—N1B2^i	124.4 (2)
C3B—N1B1—H1B1	124.4 (8)	C1B^i—C3B—C2B	6.79 (17)
C1B^i—N1B1—H1B1	144.9 (8)	N1B2^i—C3B—C2B	119.63 (17)
C3B^i—N1B1—H1B1	141.4 (7)	C1B^i—C3B—N1B1	113.65 (19)
C2B^i—C1B—C3B^i	166.4 (3)	N1B2^i—C3B—N1B1	11.62 (13)
C2B^i—C1B—N1B2	139.0 (2)	C2B—C3B—N1B1	108.49 (12)
C3B^i—C1B—N1B2	30.51 (13)	C1B^i—C3B—N1B1^i	27.79 (14)
C2B^i—C1B—N1B1	30.98 (14)	N1B2^i—C3B—N1B1^i	97.12 (15)
C3B^i—C1B—N1B1	138.6 (2)	C2B—C3B—N1B1^i	22.51 (7)
N1B2—C1B—N1B1	108.54 (12)	N1B1—C3B—N1B1^i	86.03 (11)
C2B^i—C1B—N1B2^i	47.25 (15)	C1B^i—C3B—C2B^i	95.46 (17)
C3B^i—C1B—N1B2^i	122.04 (18)	N1B2^i—C3B—C2B^i	29.35 (12)
N1B2—C1B—N1B2^i	92.00 (11)	C2B—C3B—C2B^i	90.36 (11)
N1B1—C1B—N1B2^i	16.60 (7)	N1B1—C3B—C2B^i	18.19 (8)
C2B^i—C1B—N1B1^i	123.66 (19)	N1B1^i—C3B—C2B^i	67.87 (8)
C3B^i—C1B—N1B1^i	45.58 (14)	C1B^i—C3B—H3B	127.0 (9)
N1B2—C1B—N1B1^i	15.36 (7)	N1B2^i—C3B—H3B	107.7 (9)
N1B1—C1B—N1B1^i	93.25 (11)	C2B—C3B—H3B	132.5 (9)
N1B2^i—C1B—N1B1^i	76.67 (8)	N1B1—C3B—H3B	119.0 (9)
C2B^i—C1B—H1B	98.2 (13)	N1B1^i—C3B—H3B	154.8 (9)
C3B^i—C1B—H1B	92.7 (13)	C2B^i—C3B—H3B	137.0 (9)
N1B2—C1B—H1B	122.7 (13)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^ii	1.23 (1)	2.45 (1)	3.1641 (13)	115 (1)
O4—H4···O4^ii	1.23 (1)	1.23 (1)	2.4538 (14)	180 (1)
C2—H21···O1^iii	0.958 (6)	2.797 (7)	3.6814 (19)	153.9 (7)
C2—H22···O3^iv	1.001 (7)	2.496 (8)	3.3796 (15)	147.0 (6)
N1A1—H1A1···O1	0.938 (8)	1.735 (8)	2.6715 (13)	176.6 (10)
C1A—H1A···O4^v	1.003 (8)	2.352 (8)	3.3408 (14)	168.3 (6)
N1A2—H1A2···O2^vi	0.964 (8)	1.702 (8)	2.6583 (13)	171.0 (8)
C2A—H2A···O3^vii	0.945 (7)	2.231 (7)	3.1613 (15)	167.8 (7)
C3A—H3A···O3	0.923 (7)	2.586 (7)	3.3199 (15)	136.9 (6)
C3B—H3B···O1^viii	1.018 (13)	2.473 (16)	3.0957 (19)	118.8 (10)
C2B—H2B···O2^v	0.825 (16)	2.534 (17)	3.065 (2)	123.2 (11)
C2B—H2B···O4^vi	0.825 (16)	3.094 (12)	3.525 (2)	115.2 (11)
N1B2—H1B2···O1^v	0.99 (2)	1.84 (2)	2.8261 (16)	174 (1)
N1B2—H1B2···O2^v	0.99 (2)	2.45 (2)	2.9903 (17)	114 (1)
N1B1—H1B1···O1^viii	1.03 (2)	2.41 (2)	3.0330 (16)	118 (1)
N1B1—H1B1···O2^viii	1.03 (2)	1.72 (2)	2.7492 (17)	180 (1)
C1B—H1B···O3	0.969 (16)	2.824 (19)	3.516 (2)	129.0 (13)
C1B—H1B···O4^ii	0.969 (16)	2.576 (16)	3.476 (2)	154.4 (17)

Symmetry codes: (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z+1; (vi) x, y+1, z+1; (vii) −x+1, −y+1, −z+2; (viii) x, y, z+1.

(m330)

Crystal data

C6H5O8·3(C3H5N2)	Z = 2
Mr = 206.18	F(000) = 216
Triclinic, P1	Dx = 1.414 Mg m^−3
a = 7.295 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.280 (2) Å	Cell parameters from 4538 reflections
c = 9.249 (2) Å	θ = 4–56.1°
α = 115.79 (3)°	µ = 0.12 mm^−1
β = 103.12 (3)°	T = 330 K
γ = 91.91 (3)°	Unshaped, colorless
V = 484.3 (2) Å^3	0.34 × 0.32 × 0.21 mm

Data collection

Xcalibur-Oxford Diffraction diffractometer	1217 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.093
CCD scans	θmax = 28.1°, θmin = 2.9°
Absorption correction: numerical CrysAlis v171.33.42	h = −9→8
Tmin = 0.968, Tmax = 1.253	k = −10→10
4534 measured reflections	l = −11→11
2174 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.025P)^2 + 0.025P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.116	(Δ/σ)max = 0.085
S = 1.09	Δρmax = 0.17 e Å^−3
2174 reflections	Δρmin = −0.20 e Å^−3
204 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.114 (3)

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.22508 (10)	0.42168 (8)	0.39009 (7)	0.0560 (2)
O2	0.21472 (10)	0.17168 (8)	0.16536 (7)	0.0579 (2)
O3	0.32732 (10)	0.14313 (10)	0.65214 (7)	0.0731 (3)
O4	0.08773 (10)	0.05745 (10)	0.42937 (7)	0.0796 (2)
C1	0.26420 (12)	0.26448 (11)	0.31948 (9)	0.0405 (3)
C2	0.37857 (13)	0.18846 (13)	0.42750 (10)	0.0504 (3)
C3	0.26036 (14)	0.12818 (11)	0.51478 (10)	0.0463 (3)
N1A1	0.29127 (11)	0.63347 (10)	0.71905 (8)	0.0469 (2)
C1A	0.23064 (13)	0.79029 (12)	0.78717 (10)	0.0477 (3)
N1A2	0.29507 (10)	0.86033 (10)	0.94957 (8)	0.0474 (2)
C2A	0.40044 (14)	0.74436 (13)	0.98708 (10)	0.0528 (3)
C3A	0.39871 (14)	0.60284 (13)	0.84372 (11)	0.0543 (3)
N1B1	0.0687 (2)	0.40947 (19)	1.05048 (17)	0.0480 (5)	0.5
C1B	0.0063 (3)	0.3815 (3)	0.8943 (2)	0.0579 (7)	0.5
N1B2	−0.0627 (2)	0.5243 (2)	0.89244 (16)	0.0492 (5)	0.5
C2B	−0.0367 (3)	0.6520 (3)	1.0521 (2)	0.0566 (7)	0.5
C3B	0.0488 (3)	0.5830 (3)	1.1552 (2)	0.0577 (7)	0.5
H3B	0.071 (2)	0.627 (2)	1.2757 (18)	0.048 (5)*	0.5
H2B	−0.075 (2)	0.754 (2)	1.0758 (17)	0.043 (5)*	0.5
H1B2	−0.112 (2)	0.558 (2)	0.7997 (18)	0.065 (6)*	0.5
H1B1	0.120 (3)	0.309 (2)	1.080 (2)	0.106 (8)*	0.5
H1B	0.002 (3)	0.279 (3)	0.801 (2)	0.083 (7)*	0.5
H4	0.0000	0.0000	0.5000	0.114 (6)*
H21	0.4814 (13)	0.2835 (12)	0.5116 (11)	0.071 (3)*
H22	0.4276 (12)	0.0860 (12)	0.3566 (10)	0.066 (3)*
H1A1	0.2716 (12)	0.5577 (12)	0.6055 (10)	0.070 (3)*
H1A	0.1536 (13)	0.8459 (13)	0.7297 (11)	0.073 (3)*
H1A2	0.2770 (12)	0.9651 (12)	1.0323 (11)	0.071 (3)*
H2A	0.4578 (13)	0.7779 (12)	1.0997 (10)	0.066 (3)*
H3A	0.4503 (14)	0.5055 (14)	0.8252 (12)	0.090 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0823 (4)	0.0429 (3)	0.0378 (3)	0.0182 (3)	0.0097 (3)	0.0163 (2)
O2	0.0829 (4)	0.0519 (3)	0.0335 (3)	0.0230 (3)	0.0103 (3)	0.0162 (2)
O3	0.0771 (5)	0.0984 (4)	0.0429 (3)	0.0042 (4)	−0.0037 (3)	0.0416 (2)
O4	0.0714 (4)	0.1104 (4)	0.0632 (3)	−0.0266 (3)	−0.0121 (3)	0.0622 (2)
C1	0.0452 (5)	0.0421 (4)	0.0364 (3)	0.0052 (4)	0.0104 (3)	0.0202 (3)
C2	0.0485 (5)	0.0583 (5)	0.0467 (4)	0.0123 (4)	0.0052 (4)	0.0293 (3)
C3	0.0595 (5)	0.0408 (4)	0.0373 (4)	0.0099 (4)	0.0005 (4)	0.0224 (3)
N1A1	0.0550 (4)	0.0456 (4)	0.0338 (3)	0.0095 (3)	0.0072 (3)	0.0146 (3)
C1A	0.0533 (5)	0.0469 (4)	0.0405 (4)	0.0094 (4)	0.0078 (4)	0.0200 (3)
N1A2	0.0568 (4)	0.0414 (4)	0.0370 (3)	0.0076 (3)	0.0077 (3)	0.0141 (3)
C2A	0.0619 (6)	0.0526 (5)	0.0368 (4)	0.0090 (4)	0.0014 (4)	0.0196 (3)
C3A	0.0644 (6)	0.0494 (5)	0.0459 (4)	0.0166 (4)	0.0068 (4)	0.0222 (3)
N1B1	0.0599 (9)	0.0401 (7)	0.0397 (6)	0.0064 (7)	0.0045 (6)	0.0186 (5)
C1B	0.0653 (12)	0.0670 (10)	0.0459 (8)	0.0132 (10)	0.0051 (8)	0.0341 (7)
N1B2	0.0661 (9)	0.0441 (7)	0.0354 (6)	0.0087 (7)	0.0035 (6)	0.0212 (5)
C2B	0.0687 (12)	0.0493 (9)	0.0521 (9)	0.0219 (9)	0.0134 (9)	0.0238 (7)
C3B	0.0693 (12)	0.0572 (10)	0.0461 (9)	0.0153 (10)	0.0123 (9)	0.0242 (7)

Geometric parameters (Å, º)

O1—C1	1.2538 (11)	N1B1—H1B1	1.04 (2)
O2—C1	1.2439 (10)	C1B—C2B^i	0.668 (3)
O3—C3	1.2022 (11)	C1B—C3B^i	0.706 (3)
O4—C3	1.2844 (12)	C1B—N1B2	1.305 (3)
O4—H4	1.2258 (8)	C1B—N1B2^i	1.715 (2)
C1—C2	1.5147 (15)	C1B—N1B1^i	1.725 (3)
C2—C3	1.5107 (16)	C1B—H1B	0.903 (18)
C2—H21	0.975 (8)	N1B2—N1B1^i	0.5845 (19)
C2—H22	0.959 (9)	N1B2—C3B^i	0.824 (2)
N1A1—C1A	1.3158 (12)	N1B2—C2B	1.355 (2)
N1A1—C3A	1.3659 (13)	N1B2—C1B^i	1.715 (2)
N1A1—H1A1	0.932 (8)	N1B2—C2B^i	1.863 (3)
C1A—N1A2	1.3102 (12)	N1B2—H1B2	1.008 (18)
C1A—H1A	0.951 (11)	C2B—C1B^i	0.668 (3)
N1A2—C2A	1.3606 (14)	C2B—N1B1^i	0.828 (2)
N1A2—H1A2	0.912 (8)	C2B—C3B	1.361 (3)
C2A—C3A	1.3307 (13)	C2B—N1B2^i	1.863 (3)
C2A—H2A	0.938 (9)	C2B—C3B^i	2.034 (3)
C3A—H3A	0.866 (12)	C2B—H2B	0.847 (16)
N1B1—N1B2^i	0.5845 (19)	C3B—C1B^i	0.706 (3)
N1B1—C2B^i	0.828 (2)	C3B—N1B2^i	0.824 (2)
N1B1—C1B	1.323 (2)	C3B—N1B1^i	1.930 (3)
N1B1—C3B	1.375 (2)	C3B—C2B^i	2.034 (3)
N1B1—C1B^i	1.725 (3)	C3B—H3B	0.981 (15)
N1B1—C3B^i	1.930 (3)
C3—O4—H4	112.83 (7)	N1B1—C1B—H1B	127.3 (16)
O2—C1—O1	122.29 (9)	N1B2^i—C1B—H1B	143.7 (16)
O2—C1—C2	119.66 (8)	N1B1^i—C1B—H1B	138.9 (15)
O1—C1—C2	118.05 (7)	N1B1^i—N1B2—C3B^i	154.5 (4)
C3—C2—C1	112.56 (8)	N1B1^i—N1B2—C1B	127.6 (3)
C3—C2—H21	108.6 (6)	C3B^i—N1B2—C1B	28.86 (17)
C1—C2—H21	108.0 (7)	N1B1^i—N1B2—C2B	19.6 (2)
C3—C2—H22	109.0 (6)	C3B^i—N1B2—C2B	136.5 (3)
C1—C2—H22	107.6 (6)	C1B—N1B2—C2B	108.37 (16)
H21—C2—H22	111.1 (7)	N1B1^i—N1B2—C1B^i	40.2 (2)
O3—C3—O4	123.83 (10)	C3B^i—N1B2—C1B^i	115.3 (2)
O3—C3—C2	121.38 (9)	C1B—N1B2—C1B^i	87.35 (14)
O4—C3—C2	114.77 (8)	C2B—N1B2—C1B^i	21.27 (12)
C1A—N1A1—C3A	108.34 (8)	N1B1^i—N1B2—C2B^i	114.2 (3)
C1A—N1A1—H1A1	126.8 (7)	C3B^i—N1B2—C2B^i	41.54 (18)
C3A—N1A1—H1A1	124.7 (6)	C1B—N1B2—C2B^i	13.51 (10)
N1A2—C1A—N1A1	108.80 (9)	C2B—N1B2—C2B^i	95.19 (14)
N1A2—C1A—H1A	124.7 (5)	C1B^i—N1B2—C2B^i	74.04 (11)
N1A1—C1A—H1A	126.5 (5)	N1B1^i—N1B2—H1B2	100.0 (9)
C1A—N1A2—C2A	108.53 (8)	C3B^i—N1B2—H1B2	104.7 (9)
C1A—N1A2—H1A2	130.9 (6)	C1B—N1B2—H1B2	132.3 (9)
C2A—N1A2—H1A2	120.5 (7)	C2B—N1B2—H1B2	118.8 (9)
C3A—C2A—N1A2	107.37 (9)	C1B^i—N1B2—H1B2	140.0 (9)
C3A—C2A—H2A	134.5 (6)	C2B^i—N1B2—H1B2	145.8 (9)
N1A2—C2A—H2A	118.1 (6)	C1B^i—C2B—N1B1^i	124.1 (3)
C2A—C3A—N1A1	106.96 (9)	C1B^i—C2B—N1B2	111.3 (3)
C2A—C3A—H3A	130.0 (7)	N1B1^i—C2B—N1B2	13.70 (16)
N1A1—C3A—H3A	123.0 (7)	C1B^i—C2B—C3B	8.1 (2)
N1B2^i—N1B1—C2B^i	146.7 (4)	N1B1^i—C2B—C3B	121.8 (3)
N1B2^i—N1B1—C1B	123.2 (3)	N1B2—C2B—C3B	108.40 (18)
C2B^i—N1B1—C1B	24.69 (19)	C1B^i—C2B—N1B2^i	27.2 (2)
N1B2^i—N1B1—C3B	15.0 (2)	N1B1^i—C2B—N1B2^i	98.1 (2)
C2B^i—N1B1—C3B	133.3 (3)	N1B2—C2B—N1B2^i	84.81 (14)
C1B—N1B1—C3B	108.98 (18)	C3B—C2B—N1B2^i	23.68 (9)
N1B2^i—N1B1—C1B^i	36.9 (2)	C1B^i—C2B—C3B^i	95.2 (3)
C2B^i—N1B1—C1B^i	110.4 (2)	N1B1^i—C2B—C3B^i	29.49 (17)
C1B—N1B1—C1B^i	86.35 (14)	N1B2—C2B—C3B^i	16.19 (11)
C3B—N1B1—C1B^i	22.97 (11)	C3B—C2B—C3B^i	92.32 (14)
N1B2^i—N1B1—C3B^i	110.4 (3)	N1B2^i—C2B—C3B^i	68.68 (10)
C2B^i—N1B1—C3B^i	36.83 (19)	C1B^i—C2B—H2B	125.8 (11)
C1B—N1B1—C3B^i	13.00 (11)	N1B1^i—C2B—H2B	108.4 (10)
C3B—N1B1—C3B^i	96.46 (13)	N1B2—C2B—H2B	122.0 (10)
C1B^i—N1B1—C3B^i	73.65 (11)	C3B—C2B—H2B	129.6 (11)
N1B2^i—N1B1—H1B1	114.5 (11)	N1B2^i—C2B—H2B	152.9 (11)
C2B^i—N1B1—H1B1	97.5 (10)	C3B^i—C2B—H2B	137.9 (10)
C1B—N1B1—H1B1	122.0 (11)	C1B^i—C3B—N1B2^i	116.9 (3)
C3B—N1B1—H1B1	129.0 (11)	C1B^i—C3B—C2B	7.7 (2)
C1B^i—N1B1—H1B1	151.2 (11)	N1B2^i—C3B—C2B	114.8 (2)
C3B^i—N1B1—H1B1	134.3 (10)	C1B^i—C3B—N1B1	107.6 (2)
C2B^i—C1B—C3B^i	164.2 (5)	N1B2^i—C3B—N1B1	10.54 (16)
C2B^i—C1B—N1B2	139.3 (3)	C2B—C3B—N1B1	104.91 (16)
C3B^i—C1B—N1B2	34.28 (19)	C1B^i—C3B—N1B1^i	24.94 (19)
C2B^i—C1B—N1B1	31.18 (19)	N1B2^i—C3B—N1B1^i	93.41 (19)
C3B^i—C1B—N1B1	142.1 (3)	C2B—C3B—N1B1^i	21.38 (9)
N1B2—C1B—N1B1	109.22 (15)	N1B1—C3B—N1B1^i	83.54 (13)
C2B^i—C1B—N1B2^i	47.4 (2)	C1B^i—C3B—C2B^i	90.4 (2)
C3B^i—C1B—N1B2^i	125.7 (3)	N1B2^i—C3B—C2B^i	27.28 (16)
N1B2—C1B—N1B2^i	92.65 (14)	C2B—C3B—C2B^i	87.68 (14)
N1B1—C1B—N1B2^i	16.57 (9)	N1B1—C3B—C2B^i	17.24 (10)
C2B^i—C1B—N1B1^i	123.9 (3)	N1B1^i—C3B—C2B^i	66.31 (10)
C3B^i—C1B—N1B1^i	49.5 (2)	C1B^i—C3B—H3B	126.8 (11)
N1B2—C1B—N1B1^i	15.58 (8)	N1B2^i—C3B—H3B	112.2 (11)
N1B1—C1B—N1B1^i	93.65 (14)	C2B—C3B—H3B	131.4 (11)
N1B2^i—C1B—N1B1^i	77.08 (11)	N1B1—C3B—H3B	122.6 (11)
C2B^i—C1B—H1B	96.3 (16)	N1B1^i—C3B—H3B	151.7 (10)
C3B^i—C1B—H1B	89.5 (15)	C2B^i—C3B—H3B	139.3 (11)
N1B2—C1B—H1B	123.4 (15)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^ii	1.23 (1)	2.43 (1)	3.1675 (14)	116 (1)
O4—H4···O4^ii	1.23 (1)	1.23 (1)	2.4516 (17)	180 (1)
C2—H21···O1^iii	0.975 (8)	2.865 (9)	3.748 (2)	151.2 (8)
C2—H22···O3^iv	0.959 (9)	2.638 (10)	3.4690 (17)	145.1 (7)
N1A1—H1A1···O1	0.932 (8)	1.752 (8)	2.6832 (14)	177.0 (9)
C1A—H1A···O4^v	0.951 (11)	2.418 (11)	3.3578 (16)	169.5 (8)
N1A2—H1A2···O2^vi	0.912 (8)	1.767 (9)	2.6698 (14)	170.4 (9)
C2A—H2A···O3^vii	0.938 (9)	2.269 (9)	3.1796 (17)	163.7 (8)
C3A—H3A···O3	0.866 (12)	2.713 (10)	3.3882 (18)	135.9 (8)
C3B—H3B···O1^viii	0.981 (15)	2.537 (18)	3.087 (3)	115.4 (12)
C2B—H2B···O2^v	0.847 (16)	2.570 (17)	3.059 (3)	117.9 (12)
C2B—H2B···O4^vi	0.847 (16)	3.052 (13)	3.526 (3)	117.7 (12)
N1B2—H1B2···O1^v	1.01 (2)	1.85 (2)	2.8425 (19)	170 (1)
N1B2—H1B2···O2^v	1.01 (2)	2.30 (2)	2.990 (2)	125 (1)
N1B1—H1B1···O1^viii	1.04 (2)	2.51 (2)	3.0442 (19)	111 (1)
N1B1—H1B1···O2^viii	1.04 (2)	1.73 (2)	2.754 (2)	170 (2)
C1B—H1B···O3	0.903 (18)	3.02 (2)	3.639 (3)	127.5 (15)
C1B—H1B···O4^ii	0.903 (18)	2.609 (18)	3.475 (2)	161 (2)

Symmetry codes: (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z+1; (vi) x, y+1, z+1; (vii) −x+1, −y+1, −z+2; (viii) x, y, z+1.