An exceptionally stable peptide nanotube system with flexible pores

The hydrophobic channels in the structure of the dipeptide L-alanyl-L-valine act as supramolecular hosts for organic solvent molecules. In a series of data collections, it is demonstrated that small molecules like acetonitrile, methanol and acetone can be removed from the channels by drying without impairing the structure of the hydrogen-bonded peptide host structure. The title compound is one of the very first organic molecules to be found to have this property. Alcohol guests larger than methanol are also absorbed, but they induce a doubling of two axes and a change in the shape and size of the pores. The observed structural modifications explain why these solvent molecules are more or less irreversibly trapped inside the channels.

S1. Comment

Text

S2. Experimental

The compound was obtained from Sigma and used as received. Crystals were grown by evaporation of an aqueous solution.

S3. Refinement

Three to five sets of exposures.

Computing details

For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997).

Figures

Fig.1: The structure with atomic numbering indicated. Displacement ellipsoids are shown at the 50% probability level, and H-atoms are shown as spheres of arbitrary size. Fig.2: Molecular packing and unit cell.

(1) L-Ala-L-Val acetonitrile solvate

Crystal data

C8.70H17.05N2.35O3	Dx = 1.177 Mg m^−3
Mr = 202.60	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P61	Cell parameters from 17994 reflections
a = 14.1635 (8) Å	θ = 2.7–37.0°
c = 9.8702 (5) Å	µ = 0.09 mm^−1
V = 1714.74 (16) Å^3	T = 150 K
Z = 6	Needle, colourless
F(000) = 658	1.50 × 0.40 × 0.30 mm

Data collection

Siemens SMART CCD diffractometer	5820 independent reflections
Radiation source: fine-focus sealed tube	5127 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.3 pixels mm^-1	θmax = 37.0°, θmin = 2.7°
Sets of exposures each taken over 0.3° ω rotation scans	h = −24→24
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −22→23
Tmin = 0.875, Tmax = 0.974	l = −16→16
33538 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0615P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.017
5820 reflections	Δρmax = 0.43 e Å^−3
187 parameters	Δρmin = −0.19 e Å^−3
14 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.2 (5)

Special details

Refinement. Refinement of F² against ALL reflections.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.69046 (4)	0.30830 (4)	0.78109 (13)	0.02159 (10)
O2	1.06106 (4)	0.57801 (5)	0.70296 (13)	0.02861 (13)
O3	0.96959 (4)	0.55591 (5)	0.51084 (13)	0.02347 (11)
N1	0.66881 (4)	0.19988 (4)	1.00429 (13)	0.01691 (9)
H1	0.6640 (9)	0.1541 (10)	1.0695 (14)	0.025*
H2	0.6183 (10)	0.1679 (10)	0.9387 (14)	0.025*
H3	0.6535 (10)	0.2430 (10)	1.0448 (14)	0.025*
N2	0.86542 (4)	0.43725 (5)	0.82559 (13)	0.01643 (9)
H4	0.9224 (9)	0.4514 (9)	0.8730 (12)	0.020*
C1	0.78142 (5)	0.26625 (5)	0.95215 (14)	0.01669 (10)
H11	0.8247 (9)	0.3059 (9)	1.0216 (13)	0.020*
C2	0.82046 (8)	0.19326 (7)	0.89221 (15)	0.03037 (16)
H21	0.8174 (8)	0.1433 (7)	0.9601 (7)	0.046*
H22	0.8942 (8)	0.2371 (4)	0.8612 (10)	0.046*
H23	0.7745 (7)	0.1532 (7)	0.8174 (10)	0.046*
C3	0.77638 (5)	0.34134 (5)	0.84543 (14)	0.01538 (10)
C4	0.87141 (5)	0.51227 (5)	0.71972 (14)	0.01592 (10)
H41	0.8104 (8)	0.4743 (5)	0.6608 (7)	0.019*
C5	0.86822 (6)	0.61113 (6)	0.78048 (14)	0.02191 (12)
H51	0.9256 (7)	0.6443 (4)	0.8510 (9)	0.026*
C6	0.75820 (7)	0.57557 (7)	0.84732 (15)	0.02915 (15)
H61	0.7411 (4)	0.5158 (8)	0.9119 (9)	0.044*
H62	0.7009 (5)	0.5499 (8)	0.7771 (7)	0.044*
H63	0.7614 (3)	0.6380 (6)	0.8963 (9)	0.044*
C7	0.89098 (9)	0.69739 (7)	0.67320 (16)	0.03567 (19)
H71	0.9611 (8)	0.7219 (7)	0.6348 (9)	0.053*
H72	0.8889 (9)	0.7573 (7)	0.7138 (5)	0.053*
H73	0.8371 (7)	0.6668 (4)	0.6040 (9)	0.053*
C8	0.97600 (5)	0.55032 (5)	0.63740 (14)	0.01736 (10)
N50	0.9942 (19)	0.0401 (19)	0.8013 (19)	0.136 (6)*	0.170 (6)
C51	0.971 (2)	0.0247 (19)	0.9127 (19)	0.136 (6)*	0.170 (6)
C52	0.943 (3)	−0.004 (4)	1.056 (2)	0.177 (7)*	0.204 (7)
N60	0.9434 (12)	−0.0940 (14)	1.095 (3)	0.063 (4)*	0.092 (6)
C61	0.9198 (13)	−0.0580 (19)	0.983 (2)	0.063 (4)*	0.092 (6)
C62	0.911 (2)	−0.012 (2)	0.875 (2)	0.082 (6)*	0.110 (8)
N70	0.9780 (7)	−0.109 (5)	1.099 (4)	0.104 (12)*	0.060 (8)
C71	0.9206 (7)	−0.123 (4)	1.011 (4)	0.104 (12)*	0.060 (8)
C72	0.843 (4)	−0.136 (5)	0.903 (4)	0.135 (15)*	0.072 (9)
N80	0.9165 (19)	−0.126 (3)	0.979 (2)	0.085 (10)*	0.054 (6)
C81	0.9131 (19)	−0.104 (3)	0.869 (2)	0.085 (10)*	0.054 (6)
C82	0.907 (4)	−0.068 (4)	0.732 (3)	0.111 (13)*	0.065 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0172 (2)	0.0210 (2)	0.0216 (2)	0.00579 (16)	−0.00537 (17)	0.00320 (17)
O2	0.0163 (2)	0.0433 (3)	0.0230 (3)	0.0124 (2)	−0.00079 (17)	0.0100 (2)
O3	0.01656 (19)	0.0352 (3)	0.01329 (19)	0.00888 (18)	0.00110 (16)	0.00024 (18)
N1	0.0184 (2)	0.0149 (2)	0.0143 (2)	0.00599 (17)	0.00010 (17)	0.00081 (17)
N2	0.0141 (2)	0.0188 (2)	0.0137 (2)	0.00622 (17)	−0.00090 (15)	0.00294 (16)
C1	0.0167 (2)	0.0177 (2)	0.0151 (2)	0.0082 (2)	−0.00038 (18)	0.00161 (19)
C2	0.0382 (4)	0.0326 (4)	0.0315 (4)	0.0261 (3)	0.0082 (3)	0.0057 (3)
C3	0.0157 (2)	0.0170 (2)	0.0128 (2)	0.00771 (18)	−0.00010 (18)	0.00072 (17)
C4	0.0146 (2)	0.0187 (2)	0.0128 (2)	0.00710 (19)	0.00057 (17)	0.00305 (18)
C5	0.0240 (3)	0.0214 (3)	0.0205 (3)	0.0114 (2)	0.0017 (2)	0.0017 (2)
C6	0.0325 (3)	0.0325 (3)	0.0275 (3)	0.0200 (3)	0.0092 (3)	0.0029 (3)
C7	0.0464 (5)	0.0272 (3)	0.0388 (5)	0.0224 (3)	0.0127 (4)	0.0122 (3)
C8	0.0146 (2)	0.0208 (2)	0.0153 (2)	0.0078 (2)	0.00085 (17)	0.00316 (18)

Geometric parameters (Å, º)

O1—C3	1.2384 (8)	C2—H22	0.9599
O2—C8	1.2456 (8)	C2—H23	0.9599
O3—C8	1.2578 (8)	C4—C8	1.5318 (9)
N1—C1	1.4809 (8)	C4—C5	1.5445 (10)
N1—H1	0.892 (14)	C4—H41	0.9534
N1—H2	0.901 (13)	C5—C7	1.5245 (11)
N1—H3	0.844 (13)	C5—C6	1.5272 (11)
N2—C3	1.3270 (8)	C5—H51	0.9921
N2—C4	1.4623 (8)	C6—H61	0.9883
N2—H4	0.865 (12)	C6—H62	0.9883
C1—C2	1.5153 (10)	C6—H63	0.9883
C1—C3	1.5236 (8)	C7—H71	0.9518
C1—H11	0.904 (12)	C7—H72	0.9518
C2—H21	0.9599	C7—H73	0.9518
C1—N1—H1	112.3 (8)	C8—C4—C5	110.40 (5)
C1—N1—H2	113.7 (8)	N2—C4—H41	108.6
H1—N1—H2	113.6 (11)	C8—C4—H41	108.6
C1—N1—H3	106.8 (9)	C5—C4—H41	108.6
H1—N1—H3	103.3 (13)	C7—C5—C6	109.65 (7)
H2—N1—H3	106.2 (11)	C7—C5—C4	111.50 (6)
C3—N2—C4	121.97 (5)	C6—C5—C4	110.88 (6)
C3—N2—H4	117.2 (8)	C7—C5—H51	108.2
C4—N2—H4	120.6 (8)	C6—C5—H51	108.2
N1—C1—C2	110.31 (6)	C4—C5—H51	108.2
N1—C1—C3	105.78 (5)	C5—C6—H61	109.5
C2—C1—C3	111.51 (6)	C5—C6—H62	109.5
N1—C1—H11	108.1 (8)	H61—C6—H62	109.5
C2—C1—H11	110.8 (7)	C5—C6—H63	109.5
C3—C1—H11	110.1 (7)	H61—C6—H63	109.5
C1—C2—H21	109.5	H62—C6—H63	109.5
C1—C2—H22	109.5	C5—C7—H71	109.5
H21—C2—H22	109.5	C5—C7—H72	109.5
C1—C2—H23	109.5	H71—C7—H72	109.5
H21—C2—H23	109.5	C5—C7—H73	109.5
H22—C2—H23	109.5	H71—C7—H73	109.5
O1—C3—N2	124.23 (6)	H72—C7—H73	109.5
O1—C3—C1	118.09 (5)	O2—C8—O3	125.80 (6)
N2—C3—C1	117.66 (5)	O2—C8—C4	116.62 (6)
N2—C4—C8	109.22 (5)	O3—C8—C4	117.48 (6)
N2—C4—C5	111.34 (5)
C4—N2—C3—O1	−2.58 (10)	N2—C4—C5—C7	171.72 (6)
C4—N2—C3—C1	175.98 (6)	C8—C4—C5—C7	50.23 (8)
N1—C1—C3—O1	−30.34 (8)	N2—C4—C5—C6	−65.79 (7)
C2—C1—C3—O1	89.59 (8)	C8—C4—C5—C6	172.71 (6)
N1—C1—C3—N2	151.01 (6)	N2—C4—C8—O2	−45.24 (8)
C2—C1—C3—N2	−89.05 (8)	C5—C4—C8—O2	77.50 (8)
C3—N2—C4—C8	−130.56 (6)	N2—C4—C8—O3	138.13 (6)
C3—N2—C4—C5	107.26 (7)	C5—C4—C8—O3	−99.13 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.892 (14)	1.868 (13)	2.6916 (8)	152.8 (11)
N1—H2···O2^ii	0.901 (13)	1.878 (13)	2.7170 (8)	154.1 (12)
N1—H3···O1^iii	0.844 (13)	1.893 (13)	2.6675 (8)	152.0 (12)
N2—H4···O3^iv	0.865 (12)	2.088 (12)	2.9304 (8)	164.2 (11)
C1—H11···O2^iv	0.904 (12)	2.422 (12)	3.3242 (9)	176.2 (10)

Symmetry codes: (i) −x+y+1, −x+1, z+2/3; (ii) x−y, x−1, z+1/6; (iii) −y+1, x−y, z+1/3; (iv) −x+2, −y+1, z+1/2.

(2) L-Ala-L-Val

Crystal data

C8H16N2O3	Dx = 1.069 Mg m^−3
Mr = 188.23	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P61	Cell parameters from 18212 reflections
a = 14.2957 (3) Å	θ = 2.6–37.0°
c = 9.9077 (2) Å	µ = 0.08 mm^−1
V = 1753.53 (5) Å^3	T = 150 K
Z = 6	Needle, colourless
F(000) = 612	1.50 × 0.40 × 0.30 mm

Data collection

Siemens SMART CCD diffractometer	5946 independent reflections
Radiation source: fine-focus sealed tube	5279 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.3 pixels mm^-1	θmax = 37.0°, θmin = 2.6°
Sets of exposures each taken over 0.3° ω rotation scans	h = −23→23
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −24→24
Tmin = 0.884, Tmax = 0.976	l = −16→16
35248 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0629P)^2 + 0.0354P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
5946 reflections	Δρmax = 0.43 e Å^−3
141 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (5)

Special details

Refinement. Refinement of F² against ALL reflections.

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

	x	y	z	Uiso*/Ueq
O1	0.61815 (5)	0.30928 (4)	0.82073 (6)	0.02223 (10)
O2	0.51421 (6)	−0.06021 (5)	0.73998 (6)	0.03088 (14)
O3	0.58520 (5)	0.03062 (4)	0.54815 (6)	0.02422 (11)
N1	0.53154 (5)	0.33108 (5)	1.04328 (6)	0.01760 (9)
H1	0.4877 (11)	0.3377 (10)	1.1089 (14)	0.026*
H2	0.5457 (10)	0.3799 (10)	0.9746 (14)	0.026*
H3	0.5931 (11)	0.3491 (10)	1.0832 (14)	0.026*
N2	0.57020 (5)	0.13444 (4)	0.86341 (6)	0.01731 (10)
H4	0.5280 (9)	0.0748 (9)	0.9137 (13)	0.021*
C1	0.48548 (5)	0.21886 (5)	0.99154 (7)	0.01738 (10)
H11	0.4839 (9)	0.1766 (10)	1.0608 (13)	0.021*
C2	0.37395 (6)	0.17997 (8)	0.93201 (9)	0.03142 (17)
H21	0.3282 (5)	0.1813 (8)	0.9989 (8)	0.047*
H22	0.3457 (5)	0.1091 (8)	0.8999 (10)	0.047*
H23	0.37919 (14)	0.2254 (7)	0.8605 (10)	0.047*
C3	0.56476 (5)	0.22359 (5)	0.88423 (6)	0.01584 (10)
C4	0.63852 (5)	0.12810 (5)	0.75720 (6)	0.01665 (10)
H41	0.6613 (3)	0.1881 (8)	0.6990 (8)	0.020*
C5	0.74004 (6)	0.13120 (6)	0.81778 (8)	0.02336 (13)
H51	0.7146 (3)	0.0709 (8)	0.8915 (9)	0.028*
C6	0.80339 (8)	0.10900 (10)	0.71047 (12)	0.0397 (2)
H61	0.8675 (8)	0.1093 (9)	0.7538 (5)	0.060*
H62	0.8294 (8)	0.1668 (8)	0.6388 (9)	0.060*
H63	0.7551 (5)	0.0362 (8)	0.6680 (9)	0.060*
C7	0.81403 (7)	0.24056 (8)	0.88540 (9)	0.03114 (16)
H71	0.8720 (8)	0.2379 (3)	0.9311 (10)	0.047*
H72	0.7730 (5)	0.2560 (4)	0.9496 (10)	0.047*
H73	0.8434 (7)	0.2964 (6)	0.8178 (7)	0.047*
C8	0.57223 (5)	0.02434 (5)	0.67475 (7)	0.01837 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0271 (2)	0.0176 (2)	0.0225 (2)	0.01150 (19)	0.00869 (19)	0.00532 (18)
O2	0.0373 (3)	0.0169 (2)	0.0249 (3)	0.0034 (2)	0.0122 (2)	0.00076 (19)
O3	0.0343 (3)	0.0173 (2)	0.0141 (2)	0.00772 (19)	−0.00049 (19)	−0.00099 (16)
N1	0.0222 (2)	0.0191 (2)	0.0152 (2)	0.0130 (2)	0.00031 (19)	−0.00013 (18)
N2	0.0216 (2)	0.0148 (2)	0.0147 (2)	0.00855 (18)	0.00397 (17)	0.00099 (16)
C1	0.0186 (2)	0.0175 (2)	0.0158 (2)	0.0089 (2)	0.00224 (19)	0.00055 (19)
C2	0.0189 (3)	0.0398 (4)	0.0325 (4)	0.0124 (3)	−0.0025 (3)	−0.0079 (3)
C3	0.0174 (2)	0.0160 (2)	0.0135 (2)	0.00788 (19)	0.00077 (18)	0.00004 (18)
C4	0.0198 (2)	0.0153 (2)	0.0136 (2)	0.0077 (2)	0.00251 (19)	−0.00056 (18)
C5	0.0236 (3)	0.0259 (3)	0.0222 (3)	0.0136 (3)	−0.0007 (2)	−0.0022 (2)
C6	0.0311 (4)	0.0545 (6)	0.0417 (5)	0.0276 (4)	−0.0015 (4)	−0.0161 (5)
C7	0.0262 (3)	0.0358 (4)	0.0296 (4)	0.0142 (3)	−0.0069 (3)	−0.0098 (3)
C8	0.0211 (3)	0.0148 (2)	0.0166 (3)	0.0069 (2)	0.0026 (2)	−0.00080 (18)

Geometric parameters (Å, º)

O1—C3	1.2426 (8)	C2—H22	0.9385
O2—C8	1.2506 (8)	C2—H23	0.9385
O3—C8	1.2646 (9)	C4—C8	1.5362 (9)
N1—C1	1.4879 (9)	C4—C5	1.5505 (10)
N1—H1	0.941 (14)	C4—H41	0.9466
N1—H2	0.922 (14)	C5—C6	1.5293 (12)
N1—H3	0.878 (13)	C5—C7	1.5356 (12)
N2—C3	1.3311 (8)	C5—H51	1.0466
N2—C4	1.4690 (8)	C6—H61	1.0093
N2—H4	0.908 (12)	C6—H62	1.0093
C1—C2	1.5207 (10)	C6—H63	1.0093
C1—C3	1.5307 (9)	C7—H71	0.9625
C1—H11	0.908 (13)	C7—H72	0.9625
C2—H21	0.9385	C7—H73	0.9625
C1—N1—H1	112.9 (8)	C8—C4—C5	110.50 (5)
C1—N1—H2	111.9 (8)	N2—C4—H41	108.5
H1—N1—H2	109.8 (11)	C8—C4—H41	108.5
C1—N1—H3	108.1 (8)	C5—C4—H41	108.5
H1—N1—H3	106.2 (13)	C6—C5—C7	109.67 (7)
H2—N1—H3	107.6 (12)	C6—C5—C4	111.59 (7)
C3—N2—C4	121.94 (5)	C7—C5—C4	110.88 (6)
C3—N2—H4	119.0 (8)	C6—C5—H51	108.2
C4—N2—H4	119.0 (8)	C7—C5—H51	108.2
N1—C1—C2	110.22 (6)	C4—C5—H51	108.2
N1—C1—C3	105.84 (5)	C5—C6—H61	109.5
C2—C1—C3	111.39 (6)	C5—C6—H62	109.5
N1—C1—H11	107.9 (8)	H61—C6—H62	109.5
C2—C1—H11	112.2 (8)	C5—C6—H63	109.5
C3—C1—H11	109.0 (8)	H61—C6—H63	109.5
C1—C2—H21	109.5	H62—C6—H63	109.5
C1—C2—H22	109.5	C5—C7—H71	109.5
H21—C2—H22	109.5	C5—C7—H72	109.5
C1—C2—H23	109.5	H71—C7—H72	109.5
H21—C2—H23	109.5	C5—C7—H73	109.5
H22—C2—H23	109.5	H71—C7—H73	109.5
O1—C3—N2	124.36 (6)	H72—C7—H73	109.5
O1—C3—C1	118.13 (6)	O2—C8—O3	125.73 (7)
N2—C3—C1	117.50 (5)	O2—C8—C4	116.70 (6)
N2—C4—C8	109.41 (5)	O3—C8—C4	117.46 (6)
N2—C4—C5	111.27 (5)
C4—N2—C3—O1	−2.44 (11)	N2—C4—C5—C6	172.12 (7)
C4—N2—C3—C1	176.15 (6)	C8—C4—C5—C6	50.38 (9)
N1—C1—C3—O1	−29.31 (8)	N2—C4—C5—C7	−65.30 (8)
C2—C1—C3—O1	90.49 (8)	C8—C4—C5—C7	172.95 (6)
N1—C1—C3—N2	152.01 (6)	N2—C4—C8—O2	−44.61 (9)
C2—C1—C3—N2	−88.19 (8)	C5—C4—C8—O2	78.23 (8)
C3—N2—C4—C8	−131.27 (6)	N2—C4—C8—O3	138.96 (7)
C3—N2—C4—C5	106.35 (7)	C5—C4—C8—O3	−98.20 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.941 (14)	1.829 (13)	2.7036 (8)	153.5 (11)
N1—H2···O2^ii	0.922 (14)	1.876 (13)	2.7307 (8)	153.2 (13)
N1—H3···O1^iii	0.878 (13)	1.891 (13)	2.6846 (8)	149.6 (12)
N2—H4···O3^iv	0.908 (12)	2.056 (12)	2.9345 (8)	162.4 (11)
C1—H11···O2^iv	0.908 (13)	2.442 (13)	3.3485 (9)	177.0 (11)

Symmetry codes: (i) −x+y+1, −x+1, z+2/3; (ii) x−y, x, z+1/6; (iii) −y+1, x−y, z+1/3; (iv) −x+1, −y, z+1/2.

(3) L-Ala-L-Val methanol solvate

Crystal data

C10H16N2O3	Dx = 1.204 Mg m^−3
Mr = 212.25	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P61	Cell parameters from 6549 reflections
a = 14.3102 (10) Å	θ = 2.6–35.0°
c = 9.8997 (7) Å	µ = 0.09 mm^−1
V = 1755.7 (2) Å^3	T = 150 K
Z = 6	Needle, colourless
F(000) = 684	1.50 × 0.40 × 0.30 mm

Data collection

Siemens SMART CCD diffractometer	2677 independent reflections
Radiation source: fine-focus sealed tube	2357 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 8.3 pixels mm^-1	θmax = 35.0°, θmin = 2.6°
Sets of exposures each taken over 0.3° ω rotation scans	h = −23→21
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −23→22
Tmin = 0.875, Tmax = 0.974	l = −15→15
30692 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.23	w = 1/[σ^2(Fo^2) + (0.079P)^2 + 0.2629P] where P = (Fo^2 + 2Fc^2)/3
2677 reflections	(Δ/σ)max = 0.007
180 parameters	Δρmax = 0.49 e Å^−3
9 restraints	Δρmin = −0.23 e Å^−3

Special details

Refinement. Refinement of F² against ALL reflections.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.69071 (12)	0.38138 (13)	0.40282 (18)	0.0245 (3)
N1	0.79960 (12)	0.46836 (13)	0.62501 (19)	0.0196 (3)
H1	0.8448 (15)	0.5119 (12)	0.6883 (19)	0.029*
H2	0.8373 (14)	0.4623 (15)	0.5572 (15)	0.029*
H3	0.7564 (9)	0.4034 (16)	0.6606 (19)	0.029*
N2	0.56486 (12)	0.43042 (13)	0.44433 (18)	0.0195 (3)
H4	0.5480 (7)	0.4667 (14)	0.4921 (18)	0.023*
C1	0.73319 (14)	0.51429 (14)	0.5732 (2)	0.0189 (3)
H11	0.6946 (15)	0.5185 (2)	0.639 (2)	0.023*
C2	0.8059 (2)	0.62587 (17)	0.5141 (3)	0.0340 (5)
H21	0.8640 (19)	0.6757 (13)	0.5879 (19)	0.051*
H22	0.7583 (11)	0.6610 (12)	0.486 (3)	0.051*
H23	0.8465 (19)	0.6192 (3)	0.427 (3)	0.051*
C3	0.65896 (13)	0.43539 (14)	0.4658 (2)	0.0176 (3)
C5	0.39166 (17)	0.26064 (17)	0.3986 (2)	0.0266 (4)
H51	0.3542 (12)	0.2876 (9)	0.477 (2)	0.032*
C6	0.4267 (2)	0.18648 (19)	0.4666 (3)	0.0349 (5)
H61	0.3671 (17)	0.128 (2)	0.505 (3)	0.052*
H62	0.477 (2)	0.2245 (13)	0.533 (3)	0.052*
H63	0.457 (2)	0.1625 (19)	0.4026 (19)	0.052*
C7	0.3064 (2)	0.1975 (2)	0.2909 (4)	0.0450 (7)
H71	0.241 (2)	0.134 (2)	0.3350 (13)	0.067*
H72	0.3380 (12)	0.169 (2)	0.220 (3)	0.067*
H73	0.2836 (19)	0.2471 (15)	0.246 (2)	0.067*
C4	0.49019 (14)	0.36237 (14)	0.3383 (2)	0.0188 (3)	0.868 (6)
H4A	0.5297 (12)	0.3386 (7)	0.2757 (19)	0.023*
C8	0.45066 (12)	0.42724 (14)	0.2567 (3)	0.0191 (4)	0.868 (6)
O2	0.42582 (18)	0.48617 (16)	0.3209 (2)	0.0281 (5)	0.868 (6)
O3	0.4461 (2)	0.4160 (2)	0.1294 (2)	0.0259 (4)	0.868 (6)
C42	0.49019 (14)	0.36237 (14)	0.3383 (2)	0.0188 (3)	0.13
C82	0.4676 (5)	0.4357 (7)	0.2463 (10)	0.0191 (4)	0.13
O22	0.4748 (12)	0.5194 (8)	0.2934 (15)	0.036*	0.132 (6)
O32	0.4423 (17)	0.4046 (15)	0.1244 (10)	0.032*	0.132 (6)
C51	0.992 (8)	0.899 (9)	0.512 (13)	0.24 (6)*	0.27 (8)
C52	0.957 (8)	0.841 (9)	0.662 (12)	0.27 (8)*	0.28 (8)
C53	0.975 (10)	0.843 (9)	0.372 (13)	0.13 (5)*	0.10 (4)
C54	1.048 (6)	0.857 (6)	0.305 (9)	0.16 (4)*	0.21 (5)
C55	1.051 (4)	0.940 (5)	0.328 (6)	0.19 (3)*	0.33 (6)
C56	0.998 (4)	0.776 (5)	0.782 (7)	0.20 (4)*	0.29 (5)
C57	1.007 (5)	0.871 (5)	0.853 (7)	0.14 (3)*	0.19 (4)
C58	1.019 (9)	0.983 (7)	0.727 (11)	0.20 (5)*	0.22 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0266 (6)	0.0318 (7)	0.0202 (6)	0.0185 (5)	−0.0031 (5)	−0.0086 (5)
N1	0.0179 (6)	0.0267 (7)	0.0135 (5)	0.0107 (5)	−0.0006 (5)	−0.0008 (5)
N2	0.0236 (6)	0.0263 (7)	0.0131 (6)	0.0157 (6)	−0.0030 (5)	−0.0043 (5)
C1	0.0212 (7)	0.0223 (7)	0.0143 (6)	0.0117 (6)	−0.0015 (6)	−0.0030 (5)
C2	0.0368 (11)	0.0230 (8)	0.0333 (11)	0.0081 (8)	−0.0047 (9)	0.0032 (8)
C3	0.0217 (7)	0.0209 (6)	0.0114 (6)	0.0115 (6)	−0.0007 (5)	−0.0010 (5)
C5	0.0263 (8)	0.0292 (9)	0.0219 (8)	0.0122 (7)	−0.0032 (7)	−0.0005 (7)
C6	0.0390 (11)	0.0305 (9)	0.0310 (10)	0.0142 (9)	−0.0055 (9)	0.0056 (9)
C7	0.0362 (12)	0.0377 (12)	0.0442 (14)	0.0059 (9)	−0.0160 (11)	0.0026 (11)
C4	0.0248 (7)	0.0238 (7)	0.0123 (6)	0.0155 (6)	−0.0037 (5)	−0.0027 (5)
C8	0.0210 (8)	0.0249 (8)	0.0156 (7)	0.0146 (7)	−0.0027 (6)	−0.0021 (6)
O2	0.0421 (11)	0.0353 (9)	0.0220 (8)	0.0306 (9)	−0.0100 (7)	−0.0113 (7)
O3	0.0434 (10)	0.0398 (11)	0.0104 (6)	0.0328 (10)	−0.0004 (6)	0.0002 (6)
C42	0.0248 (7)	0.0238 (7)	0.0123 (6)	0.0155 (6)	−0.0037 (5)	−0.0027 (5)
C82	0.0210 (8)	0.0249 (8)	0.0156 (7)	0.0146 (7)	−0.0027 (6)	−0.0021 (6)

Geometric parameters (Å, º)

O1—C3	1.242 (2)	C5—C6	1.538 (3)
N1—C1	1.491 (2)	C5—C4	1.553 (3)
N1—H1	0.8919	C5—H51	1.1185
N1—H2	0.8919	C6—H61	0.9273
N1—H3	0.8919	C6—H62	0.9273
N2—C3	1.330 (2)	C6—H63	0.9273
N2—C4	1.467 (2)	C7—H71	1.0203
N2—H4	0.8227	C7—H72	1.0203
C1—C2	1.521 (3)	C7—H73	1.0203
C1—C3	1.528 (2)	C4—C8	1.536 (3)
C1—H11	0.8727	C4—H4A	1.0058
C2—H21	1.0676	C8—O2	1.241 (3)
C2—H22	1.0676	C8—O3	1.268 (2)
C2—H23	1.0676	C82—O22	1.240 (8)
C5—C7	1.529 (3)	C82—O32	1.275 (8)
C1—N1—H1	109.5	C6—C5—C4	111.01 (17)
C1—N1—H2	109.5	C7—C5—H51	108.1
H1—N1—H2	109.5	C6—C5—H51	108.1
C1—N1—H3	109.5	C5—C6—H61	109.5
H1—N1—H3	109.5	C5—C6—H62	109.5
H2—N1—H3	109.5	H61—C6—H62	109.5
C3—N2—C4	122.14 (14)	C5—C6—H63	109.5
C3—N2—H4	118.9	H61—C6—H63	109.5
N1—C1—C2	110.05 (16)	H62—C6—H63	109.5
N1—C1—C3	105.93 (13)	C5—C7—H71	109.5
C2—C1—C3	111.48 (16)	C5—C7—H72	109.5
N1—C1—H11	109.8	H71—C7—H72	109.5
C2—C1—H11	109.8	C5—C7—H73	109.5
C3—C1—H11	109.8	H71—C7—H73	109.5
C1—C2—H21	109.5	H72—C7—H73	109.5
C1—C2—H22	109.5	N2—C4—C8	109.96 (14)
H21—C2—H22	109.5	N2—C4—C5	111.47 (15)
C1—C2—H23	109.5	C8—C4—C5	109.42 (13)
H21—C2—H23	109.5	N2—C4—H4A	108.6
H22—C2—H23	109.5	C5—C4—H4A	108.6
O1—C3—N2	124.20 (16)	O2—C8—O3	125.6 (2)
O1—C3—C1	118.27 (15)	O2—C8—C4	117.27 (18)
N2—C3—C1	117.52 (15)	O3—C8—C4	117.17 (18)
C7—C5—C6	109.7 (2)	O22—C82—O32	124.5 (9)
C7—C5—C4	111.59 (18)
C4—N2—C3—O1	−2.5 (3)	C7—C5—C4—N2	172.31 (19)
C4—N2—C3—C1	176.30 (15)	C6—C5—C4—N2	−65.0 (2)
N1—C1—C3—O1	−28.6 (2)	C7—C5—C4—C8	50.5 (2)
C2—C1—C3—O1	91.1 (2)	C6—C5—C4—C8	173.17 (18)
N1—C1—C3—N2	152.49 (15)	N2—C4—C8—O2	−42.81 (16)
C2—C1—C3—N2	−87.8 (2)	C5—C4—C8—O2	79.94 (16)
C3—N2—C4—C8	−132.66 (17)	N2—C4—C8—O3	137.23 (16)
C3—N2—C4—C5	105.81 (19)	C5—C4—C8—O3	−100.02 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.89	1.90	2.705 (3)	148
N1—H2···O2^ii	0.89	1.91	2.731 (2)	152
N1—H3···O1^iii	0.89	1.90	2.683 (2)	146
N2—H4···O3^iv	0.82	2.13	2.926 (2)	163
C1—H11···O2^iv	0.87	2.47	3.343 (2)	175

Symmetry codes: (i) −x+y+1, −x+1, z+2/3; (ii) x−y+1, x, z+1/6; (iii) −y+1, x−y, z+1/3; (iv) −x+1, −y+1, z+1/2.

(4) L-Ala-L-Val 2-propanol solvate

Crystal data

C8.51H15.60N2O3.44	Dx = 1.133 Mg m^−3
Mr = 201.05	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P61	Cell parameters from 56358 reflections
a = 28.7247 (16) Å	θ = 0.8–27.1°
c = 9.9009 (8) Å	µ = 0.09 mm^−1
V = 7074.8 (8) Å^3	T = 150 K
Z = 24	Needle, colourless
F(000) = 2597	1.50 × 0.40 × 0.30 mm

Data collection

Siemens SMART CCD diffractometer	5504 independent reflections
Radiation source: fine-focus sealed tube	5409 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8.3 pixels mm^-1	θmax = 27.1°, θmin = 0.8°
Sets of exposures each taken over 0.3° ω rotation scans	h = −36→36
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −36→36
Tmin = 0.876, Tmax = 0.974	l = −12→12
87295 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.101	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.271	w = 1/[σ^2(Fo^2) + (0.0456P)^2 + 38.7799P] where P = (Fo^2 + 2Fc^2)/3
S = 1.20	(Δ/σ)max = 0.015
5504 reflections	Δρmax = 0.52 e Å^−3
714 parameters	Δρmin = −0.56 e Å^−3
539 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −1 (3)

Special details

Refinement. Refinement of F² against ALL reflections.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.9206 (2)	0.1840 (2)	0.7578 (6)	0.0131 (11)	0.907 (7)
H1A	0.9011	0.1961	0.7176	0.020*	0.907 (7)
H2A	0.9436	0.1833	0.6986	0.020*	0.907 (7)
H3A	0.9388	0.2055	0.8263	0.020*	0.907 (7)
C1A	0.8844 (2)	0.1286 (2)	0.8096 (7)	0.0134 (13)	0.907 (7)
H11A	0.8618	0.1055	0.7361	0.016*	0.907 (7)
C2A	0.9174 (3)	0.1056 (3)	0.8690 (9)	0.0288 (17)	0.907 (7)
H21A	0.9441	0.1092	0.8049	0.043*	0.907 (7)
H22A	0.8942	0.0682	0.8896	0.043*	0.907 (7)
H23A	0.9348	0.1247	0.9501	0.043*	0.907 (7)
C3A	0.8489 (2)	0.1346 (2)	0.9183 (7)	0.0144 (13)	0.907 (7)
O1A	0.8665 (2)	0.17911 (19)	0.9739 (6)	0.0220 (12)	0.907 (7)
N2A	0.8022 (2)	0.0913 (2)	0.9428 (6)	0.0169 (12)	0.907 (7)
H4A	0.7919	0.0631	0.8939	0.020*	0.907 (7)
C41A	0.7677 (2)	0.0908 (3)	1.0522 (7)	0.0201 (15)	0.528 (12)
H41A	0.7907	0.1222	1.1080	0.024*	0.907 (7)
C81A	0.7496 (2)	0.0417 (3)	1.1457 (7)	0.0209 (16)	0.528 (12)
O21A	0.7535 (4)	0.0023 (3)	1.1014 (10)	0.025 (2)	0.528 (12)
O31A	0.7320 (4)	0.0431 (3)	1.2594 (7)	0.012 (2)	0.528 (12)
N1E	0.8953 (12)	0.1753 (8)	0.766 (3)	0.020*	0.093 (7)
H1E	0.8716	0.1837	0.7334	0.030*	0.093 (7)
H2E	0.9193	0.1803	0.7026	0.030*	0.093 (7)
H3E	0.9120	0.1961	0.8370	0.030*	0.093 (7)
C1E	0.8668 (6)	0.1178 (7)	0.8089 (19)	0.05 (4)*	0.093 (7)
H11E	0.8451	0.0950	0.7339	0.064*	0.093 (7)
C2E	0.9070 (10)	0.1012 (15)	0.853 (4)	0.080*	0.093 (7)
H21E	0.9292	0.1037	0.7782	0.120*	0.093 (7)
H22E	0.8881	0.0648	0.8857	0.120*	0.093 (7)
H23E	0.9290	0.1246	0.9244	0.120*	0.093 (7)
C3E	0.8295 (6)	0.1141 (6)	0.9269 (16)	0.07 (4)*	0.093 (7)
O1E	0.8397 (13)	0.1564 (7)	0.986 (3)	0.040 (17)*	0.093 (7)
N2E	0.7895 (9)	0.0657 (6)	0.955 (3)	0.080*	0.093 (7)
H4E	0.7884	0.0381	0.9182	0.096*	0.093 (7)
C4E	0.7469 (8)	0.0585 (7)	1.048 (3)	0.080*	0.093 (7)
H41E	0.7598	0.0892	1.1100	0.096*	0.093 (7)
C8E	0.7242 (6)	0.0054 (7)	1.1284 (15)	0.080*	0.093 (7)
O2E	0.7035 (16)	−0.0384 (7)	1.063 (3)	0.027 (13)*	0.093 (7)
O3E	0.7272 (19)	0.0080 (14)	1.2538 (16)	0.06 (2)*	0.093 (7)
C5E	0.7022	0.0540	0.9616	0.080*	0.09
H51E	0.7148	0.0861	0.9090	0.120*	0.093 (7)
H52E	0.6729	0.0493	1.0179	0.120*	0.093 (7)
H53E	0.6901	0.0236	0.9024	0.120*	0.093 (7)
C51A	0.7198 (4)	0.0981 (6)	1.0079 (19)	0.030 (2)	0.535 (14)
H51A	0.7003	0.0988	1.0884	0.036*	0.535 (14)
C61A	0.7345 (8)	0.1468 (6)	0.924 (3)	0.032 (2)	0.535 (14)
H61A	0.7596	0.1784	0.9728	0.048*	0.535 (14)
H62A	0.7028	0.1487	0.9044	0.048*	0.535 (14)
H63A	0.7507	0.1447	0.8411	0.048*	0.535 (14)
C71A	0.6819 (6)	0.0471 (5)	0.9207 (17)	0.034 (3)	0.535 (14)
H71A	0.6724	0.0151	0.9717	0.051*	0.535 (14)
H72A	0.7002	0.0471	0.8396	0.051*	0.535 (14)
H73A	0.6499	0.0479	0.8975	0.051*	0.535 (14)
C52A	0.7184 (6)	0.0923 (9)	0.992 (2)	0.030 (2)	0.381 (15)
H52A	0.7050	0.0676	0.9154	0.036*	0.381 (15)
C62A	0.7403 (12)	0.1513 (8)	0.938 (4)	0.032 (2)	0.381 (15)
H64A	0.7704	0.1609	0.8793	0.048*	0.381 (15)
H65A	0.7513	0.1759	1.0124	0.048*	0.381 (15)
H66A	0.7124	0.1529	0.8883	0.048*	0.381 (15)
C72A	0.6719 (10)	0.0793 (11)	1.084 (3)	0.068 (7)	0.381 (15)
H74A	0.6600	0.0451	1.1260	0.102*	0.381 (15)
H75A	0.6429	0.0779	1.0319	0.102*	0.381 (15)
H76A	0.6828	0.1066	1.1519	0.102*	0.381 (15)
C42A	0.7677 (2)	0.0908 (3)	1.0522 (7)	0.0201 (15)	0.386 (13)
C82A	0.7446 (3)	0.0380 (3)	1.1334 (11)	0.0209 (16)	0.386 (13)
O22A	0.7281 (5)	−0.0058 (3)	1.0690 (12)	0.024 (3)*	0.386 (13)
O32A	0.7429 (6)	0.0404 (5)	1.2587 (9)	0.019 (4)*	0.386 (13)
N1B	0.7889 (2)	0.1251 (2)	0.4267 (7)	0.0177 (12)	0.893 (5)
H1B	0.8212	0.1470	0.3921	0.027*	0.893 (5)
H2B	0.7673	0.1034	0.3623	0.027*	0.893 (5)
H3B	0.7917	0.1056	0.4925	0.027*	0.893 (5)
C1B	0.7657 (2)	0.1579 (3)	0.4829 (7)	0.0195 (14)	0.893 (5)
H11B	0.7631	0.1799	0.4110	0.023*	0.893 (5)
C2B	0.7106 (3)	0.1209 (3)	0.5403 (9)	0.0238 (16)	0.893 (5)
H21B	0.6864	0.1008	0.4684	0.036*	0.893 (5)
H22B	0.6977	0.1418	0.5857	0.036*	0.893 (5)
H23B	0.7127	0.0966	0.6033	0.036*	0.893 (5)
C3B	0.8046 (2)	0.1942 (2)	0.5908 (7)	0.0151 (13)	0.893 (5)
O1B	0.8317 (2)	0.1785 (2)	0.6529 (6)	0.0221 (11)	0.893 (5)
N2B	0.8050 (2)	0.2400 (2)	0.6179 (6)	0.0164 (12)	0.893 (5)
H4B	0.7849	0.2482	0.5712	0.020*	0.893 (5)
C4B	0.8387 (2)	0.2767 (2)	0.7244 (7)	0.0190 (15)	0.893 (5)
H41B	0.8503	0.2569	0.7830	0.023*	0.893 (5)
C5B	0.8900 (3)	0.3254 (3)	0.6640 (9)	0.0256 (17)	0.893 (5)
H51B	0.9108	0.3489	0.7390	0.031*	0.893 (5)
C8B	0.8078 (2)	0.29634 (19)	0.8121 (7)	0.0195 (15)	0.893 (5)
O2B	0.7643 (2)	0.2907 (3)	0.7682 (8)	0.0415 (17)	0.893 (5)
O3B	0.8300 (2)	0.3171 (2)	0.9246 (6)	0.0321 (13)	0.893 (5)
C6B	0.9253 (4)	0.3069 (4)	0.5936 (11)	0.036 (2)	0.893 (5)
H61B	0.9368	0.2898	0.6581	0.054*	0.893 (5)
H62B	0.9562	0.3374	0.5552	0.054*	0.893 (5)
H63B	0.9051	0.2818	0.5233	0.054*	0.893 (5)
C7B	0.8760 (4)	0.3581 (4)	0.5681 (12)	0.044 (2)	0.893 (5)
H71B	0.8527	0.3681	0.6131	0.067*	0.893 (5)
H72B	0.8582	0.3369	0.4899	0.067*	0.893 (5)
H73B	0.9084	0.3899	0.5409	0.067*	0.893 (5)
N1F	0.7699 (8)	0.0921 (10)	0.430 (3)	0.020*	0.107 (5)
H1F	0.7485	0.0684	0.3685	0.030*	0.107 (5)
H2F	0.7754	0.0750	0.4975	0.030*	0.107 (5)
H3F	0.8012	0.1151	0.3920	0.030*	0.107 (5)
C1F	0.7436 (7)	0.1225 (7)	0.4837 (19)	0.020*	0.107 (5)
H11F	0.7394	0.1429	0.4103	0.024*	0.107 (5)
C2F	0.6892 (7)	0.0834 (13)	0.541 (4)	0.05 (2)*	0.107 (5)
H21F	0.6670	0.0593	0.4716	0.068*	0.107 (5)
H22F	0.6727	0.1028	0.5762	0.068*	0.107 (5)
H23F	0.6934	0.0632	0.6128	0.068*	0.107 (5)
C3F	0.7812 (5)	0.1610 (5)	0.5903 (15)	0.04 (2)*	0.107 (5)
O1F	0.8141 (9)	0.1511 (10)	0.645 (3)	0.047 (16)*	0.107 (5)
N2F	0.7767 (8)	0.2041 (7)	0.620 (2)	0.05 (2)*	0.107 (5)
H4F	0.7505	0.2067	0.5865	0.061*	0.107 (5)
C4F	0.8153 (6)	0.2467 (6)	0.708 (2)	0.080*	0.107 (5)
H41F	0.8295	0.2303	0.7706	0.096*	0.107 (5)
C5F	0.8637 (11)	0.2906 (11)	0.627 (4)	0.080*	0.107 (5)
H51F	0.8769	0.2737	0.5663	0.120*	0.107 (5)
H52F	0.8918	0.3137	0.6878	0.120*	0.107 (5)
H53F	0.8522	0.3115	0.5755	0.120*	0.107 (5)
C8F	0.7897 (6)	0.2725 (6)	0.7948 (17)	0.080*	0.107 (5)
O2F	0.7737 (12)	0.3009 (11)	0.738 (3)	0.020*	0.107 (5)
O3F	0.7873 (16)	0.2623 (16)	0.9208 (17)	0.061 (19)*	0.107 (5)
N1C	0.5926 (2)	0.3183 (2)	0.2611 (6)	0.0182 (11)	0.875 (6)
H1C	0.6182	0.3134	0.2251	0.027*	0.875 (6)
H2C	0.5677	0.3120	0.1989	0.027*	0.875 (6)
H3C	0.5775	0.2958	0.3301	0.027*	0.875 (6)
C1C	0.6165 (2)	0.3745 (2)	0.3098 (7)	0.0176 (12)	0.875 (6)
H11C	0.6346	0.3995	0.2351	0.021*	0.875 (6)
C2C	0.5739 (3)	0.3847 (4)	0.3698 (10)	0.0390 (19)	0.875 (6)
H21C	0.5457	0.3754	0.3050	0.059*	0.875 (6)
H22C	0.5897	0.4220	0.3930	0.059*	0.875 (6)
H23C	0.5593	0.3632	0.4495	0.059*	0.875 (6)
C3C	0.6579 (2)	0.3805 (2)	0.4165 (6)	0.0191 (13)	0.875 (6)
O1C	0.65403 (19)	0.34117 (19)	0.4736 (6)	0.0250 (11)	0.875 (6)
N2C	0.6974 (2)	0.4311 (2)	0.4418 (6)	0.0226 (12)	0.875 (6)
H4C	0.6991	0.4571	0.3948	0.027*	0.875 (6)
C4C	0.7375 (2)	0.4428 (2)	0.5475 (8)	0.0157 (14)	0.875 (6)
H41C	0.7240	0.4116	0.6076	0.019*	0.875 (6)
C5C	0.7925 (3)	0.4533 (3)	0.4835 (9)	0.0279 (18)	0.875 (6)
H51C	0.8043	0.4824	0.4173	0.033*	0.875 (6)
C8C	0.74616 (17)	0.4914 (2)	0.6309 (7)	0.0193 (15)	0.875 (6)
O2C	0.7465 (3)	0.5290 (2)	0.5700 (7)	0.0401 (17)	0.875 (6)
O3C	0.7525 (2)	0.4882 (2)	0.7577 (6)	0.0232 (12)	0.875 (6)
C6C	0.7851 (3)	0.4023 (3)	0.4098 (10)	0.0290 (18)	0.875 (6)
H61C	0.7551	0.3892	0.3492	0.044*	0.875 (6)
H62C	0.7787	0.3750	0.4752	0.044*	0.875 (6)
H63C	0.8171	0.4111	0.3596	0.044*	0.875 (6)
C7C	0.8359 (4)	0.4702 (4)	0.5915 (13)	0.047 (3)	0.875 (6)
H71C	0.8448	0.5049	0.6263	0.071*	0.875 (6)
H72C	0.8674	0.4720	0.5526	0.071*	0.875 (6)
H73C	0.8228	0.4444	0.6636	0.071*	0.875 (6)
N1G	0.5926 (2)	0.3183 (2)	0.2611 (6)	0.0182 (11)	0.12
H1G	0.6165	0.3151	0.2111	0.027*	0.125 (6)
H2G	0.5636	0.3100	0.2115	0.027*	0.125 (6)
H3G	0.5832	0.2962	0.3315	0.027*	0.125 (6)
C1G	0.6165 (2)	0.3745 (2)	0.3098 (7)	0.0176 (12)	0.12
H11G	0.6346	0.3995	0.2351	0.021*	0.125 (6)
C2G	0.5739 (3)	0.3847 (4)	0.3698 (10)	0.0390 (19)	0.12
H21G	0.5406	0.3637	0.3224	0.059*	0.125 (6)
H22G	0.5851	0.4221	0.3616	0.059*	0.125 (6)
H23G	0.5690	0.3747	0.4635	0.059*	0.125 (6)
C3G	0.6579 (2)	0.3805 (2)	0.4165 (6)	0.0191 (13)	0.12
O1G	0.65403 (19)	0.34117 (19)	0.4736 (6)	0.0250 (11)	0.12
N2G	0.6974 (2)	0.4311 (2)	0.4418 (6)	0.0226 (12)	0.12
H4G	0.6937	0.4576	0.4163	0.027*	0.125 (6)
C4G	0.7466 (4)	0.4415 (5)	0.5120 (16)	0.06 (3)*	0.125 (6)
H4G1	0.7387	0.4093	0.5637	0.074*	0.125 (6)
C5G	0.7927 (6)	0.4528 (15)	0.407 (3)	0.080*	0.125 (6)
H51G	0.7797	0.4239	0.3428	0.120*	0.125 (6)
H52G	0.8231	0.4554	0.4540	0.120*	0.125 (6)
H53G	0.8032	0.4859	0.3605	0.120*	0.125 (6)
C8G	0.7655 (4)	0.4884 (7)	0.6111 (14)	0.080*	0.125 (6)
O2G	0.7854 (16)	0.5340 (6)	0.563 (3)	0.054 (15)*	0.125 (6)
O3G	0.7590 (19)	0.4755 (13)	0.7361 (13)	0.080*	0.125 (6)
N1D	0.7360 (2)	0.6036 (2)	0.4283 (7)	0.0189 (12)	0.919 (6)
H1D	0.7645	0.6212	0.3749	0.028*	0.919 (6)
H2D	0.7092	0.5773	0.3819	0.028*	0.919 (6)
H3D	0.7445	0.5897	0.4980	0.028*	0.919 (6)
C1D	0.7189 (2)	0.6410 (3)	0.4783 (7)	0.0207 (15)	0.919 (6)
H11D	0.7190	0.6637	0.4040	0.025*	0.919 (6)
C2D	0.6637 (3)	0.6105 (3)	0.5387 (10)	0.0307 (18)	0.919 (6)
H21D	0.6386	0.5879	0.4711	0.046*	0.919 (6)
H22D	0.6532	0.6354	0.5716	0.046*	0.919 (6)
H23D	0.6639	0.5888	0.6121	0.046*	0.919 (6)
C3D	0.7612 (2)	0.6761 (2)	0.5848 (7)	0.0165 (13)	0.919 (6)
O1D	0.7862 (2)	0.65681 (19)	0.6447 (6)	0.0238 (12)	0.919 (6)
N2D	0.7685 (2)	0.7248 (2)	0.6072 (6)	0.0193 (12)	0.919 (6)
H4D	0.7517	0.7361	0.5576	0.023*	0.919 (6)
C4D	0.8041 (2)	0.7598 (2)	0.7126 (7)	0.0179 (14)	0.919 (6)
H41D	0.8134	0.7387	0.7732	0.022*	0.919 (6)
C5D	0.8570 (3)	0.8068 (3)	0.6510 (9)	0.0250 (16)	0.919 (6)
H51D	0.8474	0.8256	0.5837	0.030*	0.919 (6)
C8D	0.77625 (19)	0.78425 (18)	0.7943 (7)	0.0202 (15)	0.919 (6)
O2D	0.7511 (2)	0.8017 (2)	0.7282 (6)	0.0290 (13)	0.919 (6)
O3D	0.7809 (2)	0.7856 (2)	0.9209 (6)	0.0250 (12)	0.919 (6)
C6D	0.8902 (3)	0.7844 (3)	0.5807 (9)	0.0285 (17)	0.919 (6)
H61D	0.8674	0.7559	0.5201	0.043*	0.919 (6)
H62D	0.9044	0.7708	0.6477	0.043*	0.919 (6)
H63D	0.9192	0.8127	0.5308	0.043*	0.919 (6)
C7D	0.8921 (4)	0.8470 (4)	0.7602 (11)	0.041 (2)	0.919 (6)
H71D	0.8710	0.8583	0.8108	0.061*	0.919 (6)
H72D	0.9216	0.8777	0.7183	0.061*	0.919 (6)
H73D	0.9056	0.8302	0.8198	0.061*	0.919 (6)
N1H	0.7718 (9)	0.5968 (12)	0.428 (4)	0.020*	0.049 (3)
H1H	0.7513	0.5734	0.3653	0.030*	0.049 (3)
H2H	0.7781	0.5795	0.4942	0.030*	0.049 (3)
H3H	0.8028	0.6212	0.3920	0.030*	0.049 (3)
C1H	0.7438 (7)	0.6237 (7)	0.4844 (19)	0.008 (13)*	0.081 (6)
H11H	0.7375	0.6435	0.4128	0.010*	0.081 (6)
C2H	0.6913 (8)	0.5832 (14)	0.546 (4)	0.050*	0.081 (6)
H21H	0.6690	0.5579	0.4786	0.075*	0.081 (6)
H22H	0.6734	0.6013	0.5818	0.075*	0.081 (6)
H23H	0.6977	0.5646	0.6178	0.075*	0.081 (6)
C3H	0.7825 (5)	0.6634 (5)	0.5907 (16)	0.02 (2)*	0.081 (6)
O1H	0.8151 (9)	0.6527 (10)	0.648 (3)	0.027 (14)*	0.081 (6)
N2H	0.7792 (8)	0.7070 (7)	0.617 (2)	0.07 (4)*	0.081 (6)
H4H	0.7542	0.7105	0.5789	0.078*	0.081 (6)
C4H	0.8168 (6)	0.7489 (6)	0.707 (2)	0.080*	0.081 (6)
H41H	0.8353	0.7346	0.7615	0.096*	0.081 (6)
C5H	0.8596 (13)	0.7988 (10)	0.626 (4)	0.080*	0.081 (6)
H51H	0.8758	0.7873	0.5587	0.120*	0.081 (6)
H52H	0.8869	0.8236	0.6866	0.120*	0.081 (6)
H53H	0.8425	0.8163	0.5828	0.120*	0.081 (6)
C8H	0.7870 (6)	0.7675 (6)	0.8017 (17)	0.080*	0.081 (6)
O2H	0.7616 (12)	0.7872 (13)	0.747 (3)	0.020*	0.081 (6)
O3H	0.7900 (14)	0.7616 (15)	0.9268 (17)	0.020 (12)*	0.081 (6)
N12H	0.7649	0.5784	0.4188	0.030*	0.03
O4I	0.4751 (6)	0.5334 (9)	0.086 (3)	0.21 (2)*	0.372 (19)
C1I	0.521 (2)	0.5391 (10)	0.277 (2)	0.200*	0.372 (19)
C2I	0.5112 (9)	0.5143 (6)	0.140 (2)	0.096 (14)*	0.372 (19)
C3I	0.4812 (18)	0.4541 (7)	0.141 (5)	0.16 (3)*	0.372 (19)
O4J	0.5849 (6)	0.5209 (10)	0.298 (3)	0.030 (9)*	0.177 (17)
C1J	0.5039 (8)	0.5147 (14)	0.330 (4)	0.07 (2)*	0.177 (17)
C2J	0.5370 (9)	0.5110 (10)	0.218 (3)	0.200*	0.177 (17)
C3J	0.5125 (17)	0.4560 (16)	0.156 (5)	0.09 (3)*	0.177 (17)
O4K	0.5735 (8)	0.4996 (15)	0.336 (4)	0.200*	0.24 (2)
C1K	0.5393 (17)	0.5323 (10)	0.181 (6)	0.200*	0.24 (2)
C2K	0.5334 (9)	0.4795 (10)	0.223 (3)	0.09 (2)*	0.24 (2)
C3K	0.4790 (10)	0.4415 (14)	0.281 (5)	0.066 (15)*	0.24 (2)
O4L	0.5763 (8)	0.5006 (10)	0.321 (2)	0.017 (7)*	0.187 (19)
C1L	0.4983 (13)	0.4491 (10)	0.208 (5)	0.047 (14)*	0.187 (19)
C3L	0.5453 (9)	0.5053 (10)	0.206 (3)	0.030 (10)*	0.187 (19)
C2L	0.5306 (18)	0.5472 (14)	0.240 (6)	0.064 (18)*	0.187 (19)
O1Q	1.030 (3)	1.063 (3)	0.920 (9)	0.23 (2)*	0.36 (3)
O1R	1.003 (5)	1.009 (4)	0.801 (19)	0.23 (2)*	0.26 (3)
O1S	0.951 (5)	0.993 (5)	0.861 (14)	0.23 (2)*	0.24 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.011 (2)	0.014 (2)	0.012 (2)	0.0040 (18)	0.003 (2)	−0.002 (2)
C1A	0.010 (2)	0.016 (3)	0.013 (3)	0.006 (2)	−0.002 (2)	0.001 (2)
C2A	0.032 (3)	0.030 (3)	0.030 (3)	0.020 (3)	0.002 (3)	0.005 (3)
C3A	0.013 (2)	0.015 (3)	0.014 (3)	0.006 (2)	−0.001 (2)	0.000 (2)
O1A	0.023 (2)	0.019 (2)	0.022 (2)	0.0093 (19)	0.004 (2)	−0.0059 (19)
N2A	0.013 (2)	0.017 (2)	0.013 (2)	0.002 (2)	0.000 (2)	−0.004 (2)
C41A	0.019 (2)	0.019 (2)	0.021 (3)	0.008 (2)	0.004 (2)	−0.003 (2)
C81A	0.023 (3)	0.014 (2)	0.022 (3)	0.007 (2)	0.003 (2)	−0.001 (2)
O21A	0.034 (4)	0.012 (3)	0.023 (4)	0.007 (3)	0.001 (3)	−0.003 (3)
O31A	0.012 (3)	0.013 (3)	0.010 (4)	0.005 (3)	−0.003 (3)	−0.001 (3)
C51A	0.029 (3)	0.031 (3)	0.031 (4)	0.015 (2)	0.003 (3)	−0.002 (3)
C61A	0.031 (3)	0.035 (3)	0.034 (4)	0.020 (3)	0.000 (3)	0.001 (3)
C71A	0.029 (5)	0.033 (5)	0.035 (5)	0.012 (4)	−0.004 (4)	0.002 (4)
C52A	0.029 (3)	0.031 (3)	0.031 (4)	0.015 (2)	0.003 (3)	−0.002 (3)
C62A	0.031 (3)	0.035 (3)	0.034 (4)	0.020 (3)	0.000 (3)	0.001 (3)
C72A	0.069 (8)	0.068 (8)	0.069 (8)	0.036 (5)	0.001 (5)	0.001 (5)
C42A	0.019 (2)	0.019 (2)	0.021 (3)	0.008 (2)	0.004 (2)	−0.003 (2)
C82A	0.023 (3)	0.014 (2)	0.022 (3)	0.007 (2)	0.003 (2)	−0.001 (2)
N1B	0.017 (2)	0.018 (2)	0.014 (2)	0.006 (2)	0.003 (2)	0.002 (2)
C1B	0.022 (3)	0.019 (3)	0.018 (3)	0.010 (2)	−0.003 (2)	−0.002 (2)
C2B	0.020 (3)	0.022 (3)	0.026 (3)	0.007 (2)	−0.001 (3)	−0.004 (3)
C3B	0.015 (2)	0.013 (2)	0.013 (3)	0.005 (2)	0.001 (2)	0.004 (2)
O1B	0.030 (2)	0.019 (2)	0.022 (2)	0.0163 (19)	−0.010 (2)	−0.0041 (19)
N2B	0.021 (2)	0.016 (2)	0.013 (3)	0.0100 (19)	−0.004 (2)	−0.002 (2)
C4B	0.023 (3)	0.019 (3)	0.017 (3)	0.012 (2)	−0.004 (2)	−0.003 (2)
C5B	0.028 (3)	0.023 (3)	0.025 (3)	0.012 (2)	0.003 (3)	−0.001 (3)
C8B	0.025 (3)	0.021 (3)	0.018 (3)	0.015 (2)	−0.003 (2)	−0.002 (2)
O2B	0.037 (3)	0.053 (3)	0.039 (3)	0.026 (3)	0.000 (3)	−0.011 (3)
O3B	0.040 (3)	0.041 (3)	0.027 (3)	0.030 (2)	−0.008 (2)	−0.007 (2)
C6B	0.035 (3)	0.036 (3)	0.039 (4)	0.018 (3)	0.008 (3)	−0.002 (3)
C7B	0.045 (4)	0.044 (4)	0.048 (4)	0.024 (3)	−0.004 (3)	0.008 (3)
N1C	0.021 (2)	0.015 (2)	0.015 (2)	0.0070 (16)	−0.0001 (18)	0.0002 (18)
C1C	0.017 (2)	0.019 (2)	0.018 (2)	0.0095 (18)	0.000 (2)	−0.002 (2)
C2C	0.038 (3)	0.043 (3)	0.043 (3)	0.025 (2)	−0.001 (3)	−0.007 (3)
C3C	0.016 (2)	0.022 (2)	0.018 (2)	0.0076 (18)	−0.001 (2)	−0.004 (2)
O1C	0.027 (2)	0.025 (2)	0.023 (2)	0.0121 (16)	−0.0029 (18)	0.0020 (17)
N2C	0.025 (2)	0.024 (2)	0.018 (2)	0.0122 (18)	−0.0008 (19)	0.0025 (19)
C4C	0.020 (3)	0.017 (3)	0.011 (3)	0.010 (2)	−0.003 (3)	−0.001 (2)
C5C	0.025 (3)	0.031 (3)	0.021 (3)	0.009 (3)	0.001 (3)	−0.001 (3)
C8C	0.024 (3)	0.015 (3)	0.018 (3)	0.009 (2)	0.000 (3)	0.002 (2)
O2C	0.061 (3)	0.024 (2)	0.038 (3)	0.023 (2)	−0.017 (3)	0.004 (2)
O3C	0.032 (2)	0.019 (2)	0.016 (2)	0.0100 (19)	−0.001 (2)	−0.003 (2)
C6C	0.024 (3)	0.036 (3)	0.024 (3)	0.013 (3)	−0.001 (3)	−0.009 (3)
C7C	0.039 (4)	0.054 (4)	0.047 (4)	0.022 (3)	−0.001 (3)	−0.011 (4)
N1G	0.021 (2)	0.015 (2)	0.015 (2)	0.0070 (16)	−0.0001 (18)	0.0002 (18)
C1G	0.017 (2)	0.019 (2)	0.018 (2)	0.0095 (18)	0.000 (2)	−0.002 (2)
C2G	0.038 (3)	0.043 (3)	0.043 (3)	0.025 (2)	−0.001 (3)	−0.007 (3)
C3G	0.016 (2)	0.022 (2)	0.018 (2)	0.0076 (18)	−0.001 (2)	−0.004 (2)
O1G	0.027 (2)	0.025 (2)	0.023 (2)	0.0121 (16)	−0.0029 (18)	0.0020 (17)
N2G	0.025 (2)	0.024 (2)	0.018 (2)	0.0122 (18)	−0.0008 (19)	0.0025 (19)
N1D	0.020 (2)	0.015 (2)	0.020 (3)	0.0072 (19)	0.003 (2)	0.005 (2)
C1D	0.027 (3)	0.020 (3)	0.018 (3)	0.013 (2)	−0.002 (2)	−0.005 (2)
C2D	0.027 (3)	0.034 (3)	0.032 (4)	0.016 (3)	0.000 (3)	−0.007 (3)
C3D	0.017 (2)	0.019 (3)	0.016 (3)	0.010 (2)	−0.002 (2)	0.004 (2)
O1D	0.029 (2)	0.018 (2)	0.029 (3)	0.0142 (18)	−0.007 (2)	0.002 (2)
N2D	0.021 (2)	0.025 (2)	0.017 (3)	0.015 (2)	−0.005 (2)	−0.002 (2)
C4D	0.020 (3)	0.023 (3)	0.017 (3)	0.015 (2)	0.000 (2)	0.000 (2)
C5D	0.027 (3)	0.026 (3)	0.023 (3)	0.014 (2)	0.002 (3)	−0.002 (3)
C8D	0.024 (3)	0.020 (3)	0.024 (3)	0.017 (2)	−0.002 (2)	−0.002 (2)
O2D	0.035 (2)	0.038 (3)	0.028 (3)	0.028 (2)	−0.011 (2)	−0.008 (2)
O3D	0.031 (2)	0.034 (2)	0.020 (2)	0.024 (2)	−0.001 (2)	−0.001 (2)
C6D	0.030 (3)	0.030 (3)	0.025 (3)	0.015 (3)	0.007 (3)	−0.001 (3)
C7D	0.037 (3)	0.036 (3)	0.038 (4)	0.010 (3)	0.003 (3)	−0.008 (3)

Geometric parameters (Å, º)

N1A—C1A	1.491 (8)	C4F—H41F	0.9800
N1A—H1A	0.8900	C5F—H51F	0.9600
N1A—H2A	0.8900	C5F—H52F	0.9600
N1A—H3A	0.8900	C5F—H53F	0.9600
C1A—C2A	1.518 (9)	C8F—O2F	1.254 (10)
C1A—C3A	1.553 (9)	C8F—O3F	1.275 (10)
C1A—H11A	0.9800	N1C—C1C	1.484 (8)
C2A—H21A	0.9600	N1C—H1C	0.8900
C2A—H22A	0.9600	N1C—H2C	0.8900
C2A—H23A	0.9600	N1C—H3C	0.8900
C3A—O1A	1.244 (8)	C1C—C2C	1.515 (10)
C3A—N2A	1.316 (8)	C1C—C3C	1.534 (9)
N2A—C41A	1.463 (8)	C1C—H11C	0.9800
N2A—H4A	0.8600	C2C—H21C	0.9600
C41A—C81A	1.544 (9)	C2C—H22C	0.9600
C41A—C51A	1.555 (11)	C2C—H23C	0.9600
C41A—H41A	0.9800	C3C—O1C	1.218 (8)
C81A—O31A	1.244 (9)	C3C—N2C	1.345 (8)
C81A—O21A	1.269 (10)	N2C—C4C	1.466 (8)
N1E—C1E	1.491 (9)	N2C—H4C	0.8600
N1E—H1E	0.8900	C4C—C8C	1.532 (9)
N1E—H2E	0.8900	C4C—C5C	1.584 (10)
N1E—H3E	0.8900	C4C—H41C	0.9800
C1E—C2E	1.518 (11)	C5C—C7C	1.527 (13)
C1E—C3E	1.552 (10)	C5C—C6C	1.554 (12)
C1E—H11E	0.9800	C5C—H51C	0.9800
C2E—H21E	0.9600	C8C—O2C	1.231 (9)
C2E—H22E	0.9600	C8C—O3C	1.278 (8)
C2E—H23E	0.9600	C6C—H61C	0.9600
C3E—O1E	1.244 (9)	C6C—H62C	0.9600
C3E—N2E	1.317 (9)	C6C—H63C	0.9600
N2E—C4E	1.463 (10)	C7C—H71C	0.9600
N2E—H4E	0.8600	C7C—H72C	0.9600
C4E—C5E	1.50 (3)	C7C—H73C	0.9600
C4E—C8E	1.544 (10)	C4G—C8G	1.530 (10)
C4E—H41E	0.9800	C4G—C5G	1.585 (11)
C8E—O3E	1.244 (10)	C4G—H4G1	0.9800
C8E—O2E	1.269 (11)	C5G—H51G	0.9600
C5E—H51E	0.9600	C5G—H52G	0.9600
C5E—H52E	0.9600	C5G—H53G	0.9600
C5E—H53E	0.9600	C8G—O2G	1.232 (10)
C51A—C61A	1.50 (2)	C8G—O3G	1.279 (10)
C51A—C71A	1.58 (2)	N1D—C1D	1.473 (9)
C51A—H51A	0.9800	N1D—H1D	0.8900
C61A—H61A	0.9600	N1D—H2D	0.8900
C61A—H62A	0.9600	N1D—H3D	0.8900
C61A—H63A	0.9600	C1D—C2D	1.500 (9)
C71A—H71A	0.9600	C1D—C3D	1.542 (9)
C71A—H72A	0.9600	C1D—H11D	0.9800
C71A—H73A	0.9600	C2D—H21D	0.9600
C52A—C62A	1.50 (2)	C2D—H22D	0.9600
C52A—C72A	1.58 (2)	C2D—H23D	0.9600
C52A—H52A	0.9800	C3D—O1D	1.253 (8)
C62A—H64A	0.9600	C3D—N2D	1.325 (8)
C62A—H65A	0.9600	N2D—C4D	1.455 (8)
C62A—H66A	0.9600	N2D—H4D	0.8600
C72A—H74A	0.9600	C4D—C8D	1.534 (9)
C72A—H75A	0.9600	C4D—C5D	1.565 (9)
C72A—H76A	0.9600	C4D—H41D	0.9800
C82A—O32A	1.244 (11)	C5D—C7D	1.534 (12)
C82A—O22A	1.272 (11)	C5D—C6D	1.556 (11)
N1B—C1B	1.506 (9)	C5D—H51D	0.9800
N1B—H1B	0.8900	C8D—O2D	1.250 (9)
N1B—H2B	0.8900	C8D—O3D	1.259 (9)
N1B—H3B	0.8900	C6D—H61D	0.9600
C1B—C2B	1.508 (9)	C6D—H62D	0.9600
C1B—C3B	1.520 (9)	C6D—H63D	0.9600
C1B—H11B	0.9800	C7D—H71D	0.9600
C2B—H21B	0.9600	C7D—H72D	0.9600
C2B—H22B	0.9600	C7D—H73D	0.9600
C2B—H23B	0.9600	N1H—C1H	1.474 (10)
C3B—O1B	1.238 (8)	N1H—H1H	0.8900
C3B—N2B	1.338 (8)	N1H—H2H	0.8900
N2B—C4B	1.461 (8)	N1H—H3H	0.8900
N2B—H4B	0.8600	C1H—C2H	1.500 (11)
C4B—C8B	1.538 (9)	C1H—C3H	1.542 (10)
C4B—C5B	1.558 (9)	C1H—H11H	0.9800
C4B—H41B	0.9800	C2H—H21H	0.9600
C5B—C7B	1.524 (13)	C2H—H22H	0.9600
C5B—C6B	1.528 (11)	C2H—H23H	0.9600
C5B—H51B	0.9800	C3H—O1H	1.253 (9)
C8B—O2B	1.254 (9)	C3H—N2H	1.326 (9)
C8B—O3B	1.274 (9)	N2H—C4H	1.456 (10)
C6B—H61B	0.9600	N2H—H4H	0.8600
C6B—H62B	0.9600	C4H—C8H	1.533 (10)
C6B—H63B	0.9600	C4H—C5H	1.565 (10)
C7B—H71B	0.9600	C4H—H41H	0.9800
C7B—H72B	0.9600	C5H—H51H	0.9600
C7B—H73B	0.9600	C5H—H52H	0.9600
N1F—C1F	1.506 (10)	C5H—H53H	0.9600
N1F—H1F	0.8900	C8H—O2H	1.250 (10)
N1F—H2F	0.8900	C8H—O3H	1.259 (10)
N1F—H3F	0.8900	O4I—C2I	1.491 (10)
C1F—C2F	1.507 (10)	C1I—C2I	1.496 (10)
C1F—C3F	1.519 (10)	C2I—C3I	1.498 (10)
C1F—H11F	0.9800	O4J—C2J	1.492 (13)
C2F—H21F	0.9600	C1J—C2J	1.499 (14)
C2F—H22F	0.9600	C2J—C3J	1.501 (14)
C2F—H23F	0.9600	O4K—C2K	1.492 (13)
C3F—O1F	1.238 (9)	C1K—C2K	1.500 (14)
C3F—N2F	1.340 (9)	C2K—C3K	1.502 (14)
N2F—C4F	1.461 (10)	O4L—C3L	1.492 (13)
N2F—H4F	0.8600	C1L—C3L	1.499 (14)
C4F—C8F	1.536 (10)	C3L—C2L	1.501 (14)
C4F—C5F	1.558 (11)
N1A—C1A—C2A	110.1 (5)	C3F—N2F—C4F	121.6 (10)
N1A—C1A—C3A	105.4 (5)	C3F—N2F—H4F	119.2
C2A—C1A—C3A	111.6 (6)	C4F—N2F—H4F	119.2
N1A—C1A—H11A	109.9	N2F—C4F—C8F	113.1 (9)
C2A—C1A—H11A	109.9	N2F—C4F—C5F	111.3 (9)
C3A—C1A—H11A	109.9	C8F—C4F—C5F	110.3 (9)
C1A—C2A—H21A	109.5	N2F—C4F—H41F	107.3
C1A—C2A—H22A	109.5	C8F—C4F—H41F	107.3
H21A—C2A—H22A	109.5	C5F—C4F—H41F	107.2
C1A—C2A—H23A	109.5	C4F—C5F—H51F	109.5
H21A—C2A—H23A	109.5	C4F—C5F—H52F	109.5
H22A—C2A—H23A	109.5	H51F—C5F—H52F	109.5
O1A—C3A—N2A	126.1 (6)	C4F—C5F—H53F	109.5
O1A—C3A—C1A	117.9 (5)	H51F—C5F—H53F	109.5
N2A—C3A—C1A	116.0 (5)	H52F—C5F—H53F	109.5
C3A—N2A—C41A	120.7 (5)	O2F—C8F—O3F	126.4 (11)
C3A—N2A—H4A	119.6	O2F—C8F—C4F	118.8 (9)
C41A—N2A—H4A	119.6	O3F—C8F—C4F	114.8 (9)
N2A—C41A—C81A	111.8 (6)	N1C—C1C—C2C	111.0 (5)
N2A—C41A—C51A	115.5 (9)	N1C—C1C—C3C	104.9 (5)
C81A—C41A—C51A	112.1 (7)	C2C—C1C—C3C	111.3 (6)
N2A—C41A—H41A	105.5	N1C—C1C—H11C	109.8
C81A—C41A—H41A	105.5	C2C—C1C—H11C	109.8
C51A—C41A—H41A	105.5	C3C—C1C—H11C	109.8
O31A—C81A—O21A	124.2 (8)	O1C—C3C—N2C	123.5 (6)
O31A—C81A—C41A	117.9 (7)	O1C—C3C—C1C	120.6 (5)
O21A—C81A—C41A	117.9 (7)	N2C—C3C—C1C	115.9 (6)
C1E—N1E—H1E	109.5	C3C—N2C—C4C	121.5 (6)
C1E—N1E—H2E	109.5	C3C—N2C—H4C	119.2
H1E—N1E—H2E	109.5	C4C—N2C—H4C	119.2
C1E—N1E—H3E	109.5	N2C—C4C—C8C	110.2 (5)
H1E—N1E—H3E	109.5	N2C—C4C—C5C	110.6 (6)
H2E—N1E—H3E	109.5	C8C—C4C—C5C	110.5 (5)
N1E—C1E—C2E	110.3 (9)	N2C—C4C—H41C	108.5
N1E—C1E—C3E	105.5 (8)	C8C—C4C—H41C	108.5
C2E—C1E—C3E	111.6 (9)	C5C—C4C—H41C	108.5
N1E—C1E—H11E	109.8	C7C—C5C—C6C	109.5 (7)
C2E—C1E—H11E	109.8	C7C—C5C—C4C	111.0 (7)
C3E—C1E—H11E	109.8	C6C—C5C—C4C	110.9 (6)
C1E—C2E—H21E	109.5	C7C—C5C—H51C	108.5
C1E—C2E—H22E	109.5	C6C—C5C—H51C	108.5
H21E—C2E—H22E	109.5	C4C—C5C—H51C	108.5
C1E—C2E—H23E	109.5	O2C—C8C—O3C	127.2 (7)
H21E—C2E—H23E	109.5	O2C—C8C—C4C	117.4 (6)
H22E—C2E—H23E	109.5	O3C—C8C—C4C	115.3 (6)
O1E—C3E—N2E	126.1 (10)	C5C—C6C—H61C	109.5
O1E—C3E—C1E	117.9 (9)	C5C—C6C—H62C	109.5
N2E—C3E—C1E	116.0 (8)	H61C—C6C—H62C	109.5
C3E—N2E—C4E	120.6 (10)	C5C—C6C—H63C	109.5
C3E—N2E—H4E	119.7	H61C—C6C—H63C	109.5
C4E—N2E—H4E	119.7	H62C—C6C—H63C	109.5
N2E—C4E—C5E	105.7 (19)	C5C—C7C—H71C	109.5
N2E—C4E—C8E	112.0 (9)	C5C—C7C—H72C	109.5
C5E—C4E—C8E	106.8 (12)	H71C—C7C—H72C	109.5
N2E—C4E—H41E	110.7	C5C—C7C—H73C	109.5
C5E—C4E—H41E	110.7	H71C—C7C—H73C	109.5
C8E—C4E—H41E	110.7	H72C—C7C—H73C	109.5
O3E—C8E—O2E	123.8 (10)	C8G—C4G—C5G	110.4 (8)
O3E—C8E—C4E	118.0 (9)	C8G—C4G—H4G1	108.1
O2E—C8E—C4E	118.2 (9)	C5G—C4G—H4G1	108.1
C4E—C5E—H51E	109.5	C4G—C5G—H51G	109.5
C4E—C5E—H52E	109.5	C4G—C5G—H52G	109.5
H51E—C5E—H52E	109.5	H51G—C5G—H52G	109.5
C4E—C5E—H53E	109.5	C4G—C5G—H53G	109.5
H51E—C5E—H53E	109.5	H51G—C5G—H53G	109.5
H52E—C5E—H53E	109.5	H52G—C5G—H53G	109.5
C61A—C51A—C41A	115.4 (12)	O2G—C8G—O3G	127.1 (11)
C61A—C51A—C71A	107.8 (14)	O2G—C8G—C4G	117.5 (9)
C41A—C51A—C71A	106.0 (10)	O3G—C8G—C4G	115.4 (9)
C61A—C51A—H51A	109.1	N1D—C1D—C2D	110.4 (5)
C41A—C51A—H51A	109.1	N1D—C1D—C3D	105.3 (5)
C71A—C51A—H51A	109.1	C2D—C1D—C3D	111.5 (6)
C51A—C61A—H61A	109.5	N1D—C1D—H11D	109.9
C51A—C61A—H62A	109.5	C2D—C1D—H11D	109.9
H61A—C61A—H62A	109.5	C3D—C1D—H11D	109.9
C51A—C61A—H63A	109.5	C1D—C2D—H21D	109.5
H61A—C61A—H63A	109.5	C1D—C2D—H22D	109.5
H62A—C61A—H63A	109.5	H21D—C2D—H22D	109.5
C51A—C71A—H71A	109.5	C1D—C2D—H23D	109.5
C51A—C71A—H72A	109.5	H21D—C2D—H23D	109.5
H71A—C71A—H72A	109.5	H22D—C2D—H23D	109.5
C51A—C71A—H73A	109.5	O1D—C3D—N2D	124.3 (6)
H71A—C71A—H73A	109.5	O1D—C3D—C1D	118.3 (6)
H72A—C71A—H73A	109.5	N2D—C3D—C1D	117.4 (6)
C62A—C52A—C72A	107.5 (16)	C3D—N2D—C4D	122.3 (6)
C62A—C52A—H52A	108.1	C3D—N2D—H4D	118.8
C72A—C52A—H52A	108.1	C4D—N2D—H4D	118.8
C52A—C62A—H64A	109.5	N2D—C4D—C8D	110.3 (5)
C52A—C62A—H65A	109.5	N2D—C4D—C5D	111.1 (6)
H64A—C62A—H65A	109.5	C8D—C4D—C5D	108.3 (5)
C52A—C62A—H66A	109.5	N2D—C4D—H41D	109.0
H64A—C62A—H66A	109.5	C8D—C4D—H41D	109.0
H65A—C62A—H66A	109.5	C5D—C4D—H41D	109.0
C52A—C72A—H74A	109.5	C7D—C5D—C6D	108.6 (7)
C52A—C72A—H75A	109.5	C7D—C5D—C4D	111.3 (7)
H74A—C72A—H75A	109.5	C6D—C5D—C4D	110.4 (6)
C52A—C72A—H76A	109.5	C7D—C5D—H51D	108.8
H74A—C72A—H76A	109.5	C6D—C5D—H51D	108.8
H75A—C72A—H76A	109.5	C4D—C5D—H51D	108.8
O32A—C82A—O22A	123.3 (9)	O2D—C8D—O3D	125.7 (7)
N1B—C1B—C2B	109.5 (5)	O2D—C8D—C4D	116.5 (6)
N1B—C1B—C3B	106.6 (5)	O3D—C8D—C4D	117.8 (6)
C2B—C1B—C3B	111.8 (6)	C5D—C6D—H61D	109.5
N1B—C1B—H11B	109.6	C5D—C6D—H62D	109.5
C2B—C1B—H11B	109.6	H61D—C6D—H62D	109.5
C3B—C1B—H11B	109.6	C5D—C6D—H63D	109.5
C1B—C2B—H21B	109.5	H61D—C6D—H63D	109.5
C1B—C2B—H22B	109.5	H62D—C6D—H63D	109.5
H21B—C2B—H22B	109.5	C5D—C7D—H71D	109.5
C1B—C2B—H23B	109.5	C5D—C7D—H72D	109.5
H21B—C2B—H23B	109.5	H71D—C7D—H72D	109.5
H22B—C2B—H23B	109.5	C5D—C7D—H73D	109.5
O1B—C3B—N2B	124.0 (6)	H71D—C7D—H73D	109.5
O1B—C3B—C1B	118.6 (6)	H72D—C7D—H73D	109.5
N2B—C3B—C1B	117.3 (6)	C1H—N1H—H1H	109.5
C3B—N2B—C4B	122.1 (6)	C1H—N1H—H2H	109.5
C3B—N2B—H4B	119.0	H1H—N1H—H2H	109.5
C4B—N2B—H4B	119.0	C1H—N1H—H3H	109.5
N2B—C4B—C8B	112.1 (5)	H1H—N1H—H3H	109.5
N2B—C4B—C5B	111.0 (6)	H2H—N1H—H3H	109.5
C8B—C4B—C5B	110.3 (5)	N1H—C1H—C2H	110.4 (10)
N2B—C4B—H41B	107.7	N1H—C1H—C3H	105.3 (9)
C8B—C4B—H41B	107.7	C2H—C1H—C3H	111.6 (10)
C5B—C4B—H41B	107.7	N1H—C1H—H11H	109.8
C7B—C5B—C6B	110.8 (8)	C2H—C1H—H11H	109.8
C7B—C5B—C4B	111.7 (7)	C3H—C1H—H11H	109.8
C6B—C5B—C4B	110.9 (6)	C1H—C2H—H21H	109.5
C7B—C5B—H51B	107.7	C1H—C2H—H22H	109.5
C6B—C5B—H51B	107.7	H21H—C2H—H22H	109.5
C4B—C5B—H51B	107.7	C1H—C2H—H23H	109.5
O2B—C8B—O3B	126.6 (7)	H21H—C2H—H23H	109.5
O2B—C8B—C4B	118.5 (6)	H22H—C2H—H23H	109.5
O3B—C8B—C4B	114.9 (6)	O1H—C3H—N2H	123.9 (10)
C5B—C6B—H61B	109.5	O1H—C3H—C1H	118.4 (9)
C5B—C6B—H62B	109.5	N2H—C3H—C1H	117.7 (9)
H61B—C6B—H62B	109.5	C3H—N2H—C4H	121.8 (11)
C5B—C6B—H63B	109.5	C3H—N2H—H4H	119.1
H61B—C6B—H63B	109.5	C4H—N2H—H4H	119.1
H62B—C6B—H63B	109.5	N2H—C4H—C8H	110.5 (8)
C5B—C7B—H71B	109.5	N2H—C4H—C5H	111.1 (9)
C5B—C7B—H72B	109.5	C8H—C4H—C5H	108.3 (9)
H71B—C7B—H72B	109.5	N2H—C4H—H41H	109.0
C5B—C7B—H73B	109.5	C8H—C4H—H41H	109.0
H71B—C7B—H73B	109.5	C5H—C4H—H41H	108.8
H72B—C7B—H73B	109.5	C4H—C5H—H51H	109.5
C1F—N1F—H1F	109.5	C4H—C5H—H52H	109.5
C1F—N1F—H2F	109.5	H51H—C5H—H52H	109.5
H1F—N1F—H2F	109.5	C4H—C5H—H53H	109.4
C1F—N1F—H3F	109.5	H51H—C5H—H53H	109.5
H1F—N1F—H3F	109.5	H52H—C5H—H53H	109.5
H2F—N1F—H3F	109.5	O2H—C8H—O3H	125.8 (11)
N1F—C1F—C2F	109.6 (9)	O2H—C8H—C4H	116.5 (9)
N1F—C1F—C3F	106.8 (9)	O3H—C8H—C4H	117.8 (10)
C2F—C1F—C3F	111.9 (10)	O4I—C2I—C1I	98.6 (15)
N1F—C1F—H11F	109.5	O4I—C2I—C3I	108.9 (16)
C2F—C1F—H11F	109.5	C1I—C2I—C3I	113.8 (18)
C3F—C1F—H11F	109.5	O4J—C2J—C1J	98.5 (15)
C1F—C2F—H21F	109.5	O4J—C2J—C3J	108.6 (17)
C1F—C2F—H22F	109.5	C1J—C2J—C3J	113.3 (18)
H21F—C2F—H22F	109.5	O4K—C2K—C1K	98.4 (16)
C1F—C2F—H23F	109.5	O4K—C2K—C3K	108.5 (17)
H21F—C2F—H23F	109.5	C1K—C2K—C3K	113.2 (18)
H22F—C2F—H23F	109.5	O4L—C3L—C1L	98.6 (15)
O1F—C3F—N2F	123.5 (10)	O4L—C3L—C2L	108.5 (17)
O1F—C3F—C1F	118.8 (9)	C1L—C3L—C2L	113.3 (18)
N2F—C3F—C1F	117.7 (9)
N1A—C1A—C3A—O1A	−24.0 (8)	C3F—N2F—C4F—C5F	89 (2)
C2A—C1A—C3A—O1A	95.6 (7)	N2F—C4F—C8F—O2F	−69 (2)
N1A—C1A—C3A—N2A	156.1 (6)	C5F—C4F—C8F—O2F	56 (2)
C2A—C1A—C3A—N2A	−84.4 (7)	N2F—C4F—C8F—O3F	111 (2)
O1A—C3A—N2A—C41A	−6.0 (11)	C5F—C4F—C8F—O3F	−124 (2)
C1A—C3A—N2A—C41A	174.0 (6)	N1C—C1C—C3C—O1C	−22.6 (5)
C3A—N2A—C41A—C81A	−129.0 (6)	C2C—C1C—C3C—O1C	97.5 (6)
C3A—N2A—C41A—C51A	101.3 (9)	N1C—C1C—C3C—N2C	157.7 (5)
N2A—C41A—C81A—O31A	162.2 (6)	C2C—C1C—C3C—N2C	−82.2 (6)
C51A—C41A—C81A—O31A	−66.4 (10)	O1C—C3C—N2C—C4C	−3.7 (7)
N2A—C41A—C81A—O21A	−18.0 (7)	C1C—C3C—N2C—C4C	176.0 (6)
C51A—C41A—C81A—O21A	113.4 (10)	C3C—N2C—C4C—C8C	−135.3 (5)
N1E—C1E—C3E—O1E	−19 (2)	C3C—N2C—C4C—C5C	102.2 (6)
C2E—C1E—C3E—O1E	101 (2)	N2C—C4C—C5C—C7C	175.2 (7)
N1E—C1E—C3E—N2E	161 (2)	C8C—C4C—C5C—C7C	52.9 (9)
C2E—C1E—C3E—N2E	−79 (2)	N2C—C4C—C5C—C6C	−62.9 (8)
O1E—C3E—N2E—C4E	10 (2)	C8C—C4C—C5C—C6C	174.7 (6)
C1E—C3E—N2E—C4E	−170 (2)	N2C—C4C—C8C—O2C	−39.2 (6)
C3E—N2E—C4E—C5E	96 (3)	C5C—C4C—C8C—O2C	83.5 (6)
C3E—N2E—C4E—C8E	−148 (2)	N2C—C4C—C8C—O3C	141.1 (5)
N2E—C4E—C8E—O3E	121 (3)	C5C—C4C—C8C—O3C	−96.3 (6)
C5E—C4E—C8E—O3E	−124 (3)	C5G—C4G—C8G—O2G	51 (3)
N2E—C4E—C8E—O2E	−59 (3)	C5G—C4G—C8G—O3G	−129 (3)
C5E—C4E—C8E—O2E	56 (3)	N1D—C1D—C3D—O1D	−26.1 (8)
N2A—C41A—C51A—C61A	−54.1 (18)	C2D—C1D—C3D—O1D	93.6 (8)
C81A—C41A—C51A—C61A	176.4 (15)	N1D—C1D—C3D—N2D	154.1 (6)
N2A—C41A—C51A—C71A	65.1 (11)	C2D—C1D—C3D—N2D	−86.2 (8)
C81A—C41A—C51A—C71A	−64.4 (13)	O1D—C3D—N2D—C4D	−4.8 (10)
N1B—C1B—C3B—O1B	−29.1 (8)	C1D—C3D—N2D—C4D	175.0 (5)
C2B—C1B—C3B—O1B	90.6 (8)	C3D—N2D—C4D—C8D	−133.2 (6)
N1B—C1B—C3B—N2B	154.6 (6)	C3D—N2D—C4D—C5D	106.7 (7)
C2B—C1B—C3B—N2B	−85.8 (7)	N2D—C4D—C5D—C7D	174.2 (6)
O1B—C3B—N2B—C4B	0.7 (10)	C8D—C4D—C5D—C7D	52.9 (8)
C1B—C3B—N2B—C4B	176.8 (6)	N2D—C4D—C5D—C6D	−65.1 (8)
C3B—N2B—C4B—C8B	−134.7 (6)	C8D—C4D—C5D—C6D	173.6 (6)
C3B—N2B—C4B—C5B	101.4 (7)	N2D—C4D—C8D—O2D	−44.3 (6)
N2B—C4B—C5B—C7B	60.9 (9)	C5D—C4D—C8D—O2D	77.5 (6)
C8B—C4B—C5B—C7B	−64.0 (9)	N2D—C4D—C8D—O3D	136.4 (5)
N2B—C4B—C5B—C6B	−63.3 (8)	C5D—C4D—C8D—O3D	−101.8 (6)
C8B—C4B—C5B—C6B	171.8 (7)	N1H—C1H—C3H—O1H	−27 (2)
N2B—C4B—C8B—O2B	−16.5 (6)	C2H—C1H—C3H—O1H	93 (2)
C5B—C4B—C8B—O2B	107.8 (6)	N1H—C1H—C3H—N2H	153 (2)
N2B—C4B—C8B—O3B	163.4 (5)	C2H—C1H—C3H—N2H	−87 (2)
C5B—C4B—C8B—O3B	−72.3 (6)	O1H—C3H—N2H—C4H	5.1 (17)
N1F—C1F—C3F—O1F	−22 (2)	C1H—C3H—N2H—C4H	−174.9 (16)
C2F—C1F—C3F—O1F	98 (2)	C3H—N2H—C4H—C8H	−136.4 (18)
N1F—C1F—C3F—N2F	157.9 (19)	C3H—N2H—C4H—C5H	103 (2)
C2F—C1F—C3F—N2F	−82 (2)	N2H—C4H—C8H—O2H	−61 (2)
O1F—C3F—N2F—C4F	7.8 (18)	C5H—C4H—C8H—O2H	61 (2)
C1F—C3F—N2F—C4F	−172.3 (17)	N2H—C4H—C8H—O3H	119 (2)
C3F—N2F—C4F—C8F	−146.3 (18)	C5H—C4H—C8H—O3H	−119 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1B	0.89	1.91	2.691 (8)	146
N1A—H2A···O3D^i	0.89	1.88	2.691 (8)	151
N1A—H3A···O2A^ii	0.89	1.94	2.769 (10)	155
N2A—H4A···O3D^iii	0.86	2.11	2.953 (8)	166
C1A—H11A···O2D^iii	0.98	2.39	3.373 (9)	176
N1B—H1B···O1D^i	0.89	1.90	2.707 (8)	150
N1B—H2B···O31A^iv	0.89	1.82	2.667 (10)	158
N1B—H3B···O2D^iii	0.89	1.87	2.699 (8)	154
N2B—H4B···O3C^i	0.86	2.02	2.847 (8)	161
C1B—H11B···O3C^i	0.98	2.43	3.149 (9)	129
N1C—H1C···O1C^i	0.89	1.91	2.699 (7)	146
N1C—H2C···O3C^v	0.89	1.85	2.652 (8)	150
N1C—H3C···O2B^i	0.89	1.92	2.774 (9)	162
N2C—H4C···O3B^v	0.86	2.32	3.159 (8)	167
C1C—H11C···O2B^v	0.98	2.51	3.446 (9)	159
N1D—H1D···O1A^v	0.89	1.90	2.705 (8)	149
N1D—H2D···O3B^v	0.89	2.03	2.827 (8)	149
N1D—H3D···O2C	0.89	1.91	2.702 (8)	148
N2D—H4D···O31A^vi	0.86	2.18	2.994 (10)	158
C1D—H11D···O31A^vi	0.98	2.52	3.176 (10)	124

Symmetry codes: (i) −x+y+1, −x+1, z−1/3; (ii) y+1, −x+y+1, z−1/6; (iii) y, −x+y, z−1/6; (iv) x, y, z−1; (v) −y+1, x−y, z−2/3; (vi) x−y, x, z−5/6.