Structures of N-acetyl-DL-isoleucine, N-acetyl-DL-alloisoleucine and their ammonium salts; role of ammonium ions in crystal structure formation

The crystal structures of N-acetyl-DL-isoleucine, N-acetyl-DL-alloisoleucine and their ammonium salts show that these four compounds exist as racemic compounds around room temperature. The two ammonium salts are arranged around a 2₁ screw axis, forming a helical column which consists of ammonium ions and single enantiomeric anions similar to the crystals of the ammonium salts of optically active N-acetyl-L-isoleucine and N-acetyl-D-alloisoleucine. The ammonium ion and the carboxylate ion in the helix are connected by three hydrogen bonds, the fourth hydrogen bond being formed between the ammonium ion and an external acetyl amino group of the neighboring helical column. The fourth hydrogen bond is formed between the ammonium ion and an external acetyl amino group of the neighboring 2₁ column. Ammonium N-acetyl-DL-alloisoleucinate was revealed to exist as an unstable racemic compound due to conformational similarity between the racemic and optically active compounds in the solid state and was optically resolved by fractional crystallization at 293 K.

Computing details

For all compounds, data collection: RAPID AUTO (Rigaku, 2006); cell refinement: RAPID AUTO; data reduction: RAPID AUTO. Program(s) used to solve structure: SIR2004 (Burla, et al., 2005) for Ac-DL-Ile, Ac-DL-IleNH3, Ac-DL-aIleNH3; Il Milione (Burla, et al., 2007) for Ac-DL-aIle. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure 4.0; software used to prepare material for publication: CrystalStructure 4.0 (Rigaku, 2010).

(Ac-DL-Ile)

Crystal data

C8H15NO3	Dx = 1.210 Mg m^−3
Mr = 173.21	Melting point = 115–118 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 11195 reflections
a = 7.0603 (11) Å	θ = 3.2–27.5°
b = 9.2687 (12) Å	µ = 0.09 mm^−1
c = 29.062 (4) Å	T = 123 K
V = 1901.8 (5) Å^3	Platelet, colorless
Z = 8	0.34 × 0.26 × 0.01 mm
F(000) = 752.00

Data collection

Rigaku R-AXIS RAPID diffractometer	1864 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.030
ω scans	θmax = 27.5°
Absorption correction: multi-scan ABSCOR (Rigaku, 1995)	h = −9→9
Tmin = 0.684, Tmax = 0.999	k = −11→12
16961 measured reflections	l = −37→36
2162 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	Only H-atom coordinates refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0622P)^2 + 0.4102P] where P = (Fo^2 + 2Fc^2)/3
2162 reflections	(Δ/σ)max = 0.001
169 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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

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

	x	y	z	Uiso*/Ueq
O(1)	1.39541 (11)	0.16754 (9)	0.64220 (3)	0.0273 (2)
O(2)	1.19724 (12)	0.26372 (9)	0.69415 (3)	0.0306 (3)
O(3)	0.84805 (11)	−0.15715 (8)	0.67542 (3)	0.0252 (2)
N(1)	0.91168 (13)	0.08375 (10)	0.67145 (3)	0.0213 (2)
C(1)	1.23011 (15)	0.17837 (11)	0.66374 (3)	0.0220 (3)
C(2)	1.08400 (15)	0.07395 (11)	0.64389 (4)	0.0217 (3)
C(3)	1.05642 (17)	0.10634 (13)	0.59211 (4)	0.0281 (3)
C(4)	0.9958 (2)	0.26325 (15)	0.58455 (5)	0.0379 (4)
C(5)	1.0165 (3)	0.3144 (3)	0.53482 (6)	0.0515 (4)
C(6)	0.9173 (3)	−0.00089 (19)	0.57092 (5)	0.0464 (4)
C(7)	0.81334 (14)	−0.02998 (11)	0.68695 (4)	0.0203 (3)
C(8)	0.65529 (16)	0.00067 (12)	0.72016 (4)	0.0241 (3)
H(1)	1.470 (3)	0.233 (2)	0.6540 (6)	0.048 (5)*
H(2)	1.1317 (19)	−0.0249 (15)	0.6471 (5)	0.020 (3)*
H(3)	1.183 (3)	0.0924 (15)	0.5774 (5)	0.029 (4)*
H(4)	0.861 (3)	0.273 (3)	0.5935 (7)	0.060 (6)*
H(5)	1.072 (3)	0.330 (2)	0.6054 (7)	0.057 (5)*
H(6)	0.983 (4)	0.416 (3)	0.5324 (7)	0.068 (6)*
H(7)	1.151 (4)	0.309 (3)	0.5222 (8)	0.087 (7)*
H(8)	0.937 (4)	0.253 (3)	0.5149 (8)	0.083 (7)*
H(9)	0.792 (3)	0.015 (2)	0.5864 (7)	0.057 (5)*
H(10)	0.968 (3)	−0.108 (3)	0.5751 (7)	0.061 (6)*
H(11)	0.905 (3)	0.014 (2)	0.5369 (7)	0.061 (6)*
H(12)	0.872 (3)	0.1697 (17)	0.6808 (5)	0.032 (4)*
H(13)	0.681 (3)	−0.0524 (17)	0.7478 (6)	0.040 (4)*
H(14)	0.538 (3)	−0.0394 (17)	0.7085 (6)	0.037 (4)*
H(15)	0.641 (3)	0.1049 (17)	0.7266 (5)	0.032 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.0181 (4)	0.0259 (5)	0.0380 (5)	−0.0026 (3)	−0.0004 (3)	−0.0045 (4)
O(2)	0.0269 (5)	0.0290 (5)	0.0359 (5)	−0.0054 (4)	0.0029 (4)	−0.0086 (4)
O(3)	0.0202 (4)	0.0169 (4)	0.0384 (5)	0.0005 (3)	0.0034 (3)	−0.0000 (3)
N(1)	0.0190 (5)	0.0165 (5)	0.0285 (5)	0.0002 (4)	0.0009 (4)	−0.0003 (4)
C(1)	0.0197 (6)	0.0189 (5)	0.0275 (5)	−0.0005 (4)	−0.0016 (4)	0.0031 (4)
C(2)	0.0183 (5)	0.0189 (6)	0.0281 (6)	−0.0014 (4)	0.0009 (4)	−0.0008 (4)
C(3)	0.0234 (6)	0.0328 (6)	0.0280 (6)	−0.0034 (5)	0.0010 (5)	−0.0007 (5)
C(4)	0.0369 (8)	0.0417 (8)	0.0349 (7)	0.0087 (6)	0.0040 (6)	0.0113 (6)
C(5)	0.0506 (10)	0.0612 (11)	0.0428 (9)	0.0063 (8)	0.0042 (7)	0.0207 (8)
C(6)	0.0454 (9)	0.0622 (10)	0.0315 (7)	−0.0228 (8)	−0.0034 (6)	−0.0038 (7)
C(7)	0.0164 (5)	0.0194 (5)	0.0249 (5)	0.0007 (4)	−0.0032 (4)	0.0006 (4)
C(8)	0.0218 (6)	0.0214 (6)	0.0291 (6)	0.0006 (4)	0.0025 (4)	0.0014 (4)

Geometric parameters (Å, º)

O(1)—C(1)	1.3282 (13)	C(2)—H(2)	0.981 (14)
O(2)—C(1)	1.2086 (13)	C(3)—H(3)	0.998 (15)
O(3)—C(7)	1.2497 (13)	C(4)—H(4)	0.99 (2)
N(1)—C(2)	1.4594 (15)	C(4)—H(5)	1.02 (2)
N(1)—C(7)	1.3402 (14)	C(5)—H(6)	0.97 (3)
C(1)—C(2)	1.5276 (15)	C(5)—H(7)	1.02 (3)
C(2)—C(3)	1.5468 (17)	C(5)—H(8)	0.99 (3)
C(3)—C(4)	1.5318 (19)	C(6)—H(9)	1.00 (2)
C(3)—C(6)	1.527 (2)	C(6)—H(10)	1.06 (3)
C(4)—C(5)	1.528 (3)	C(6)—H(11)	1.00 (2)
C(7)—C(8)	1.5025 (16)	C(8)—H(13)	0.959 (17)
O(1)—H(1)	0.875 (19)	C(8)—H(14)	0.967 (17)
N(1)—H(12)	0.889 (16)	C(8)—H(15)	0.989 (16)
O(1)···C(3)	2.8582 (15)	C(5)···H(11)^iii	3.51 (2)
O(1)···C(4)	3.3990 (18)	C(6)···H(1)^vi	3.540 (18)
O(2)···N(1)	2.6986 (13)	C(6)···H(4)^vii	2.95 (2)
O(2)···C(3)	3.4511 (15)	C(6)···H(6)^vii	3.14 (3)
O(2)···C(4)	3.4882 (18)	C(6)···H(8)^xiv	3.57 (3)
O(3)···C(2)	2.8641 (14)	C(6)···H(11)^xiv	3.38 (2)
O(3)···C(6)	3.3999 (18)	C(7)···H(1)^viii	3.573 (19)
N(1)···C(4)	3.0820 (18)	C(7)···H(1)^vi	2.841 (19)
N(1)···C(6)	3.0253 (18)	C(7)···H(4)^vii	3.498 (19)
C(1)···C(4)	2.9413 (18)	C(7)···H(12)^vii	3.079 (16)
C(1)···C(7)	3.5837 (15)	C(7)···H(13)^v	3.221 (17)
C(3)···C(7)	3.4840 (17)	C(7)···H(14)^v	3.430 (16)
C(5)···C(6)	3.183 (3)	C(7)···H(15)^vii	3.589 (15)
C(6)···C(7)	3.461 (2)	C(8)···H(1)^viii	3.173 (18)
O(1)···O(3)^i	2.6178 (12)	C(8)···H(12)^vii	3.279 (16)
O(1)···C(8)^ii	3.3003 (15)	C(8)···H(13)^x	3.511 (17)
O(2)···O(3)^i	3.3378 (13)	C(8)···H(14)^v	3.428 (17)
O(2)···C(2)^i	3.5759 (14)	H(1)···O(3)^i	1.752 (19)
O(2)···C(8)^iii	3.4044 (15)	H(1)···N(1)^ii	3.452 (19)
O(2)···C(8)^iv	3.4798 (15)	H(1)···N(1)^i	3.391 (19)
O(2)···C(8)^v	3.4977 (15)	H(1)···C(2)^i	3.192 (19)
O(3)···O(1)^vi	2.6178 (12)	H(1)···C(6)^i	3.540 (18)
O(3)···O(2)^vi	3.3378 (13)	H(1)···C(7)^ii	3.573 (19)
O(3)···N(1)^vii	3.0238 (13)	H(1)···C(7)^i	2.841 (19)
O(3)···C(1)^vi	3.3630 (14)	H(1)···C(8)^ii	3.173 (18)
O(3)···C(8)^vii	3.4278 (14)	H(1)···H(2)^i	2.36 (3)
N(1)···O(3)^iii	3.0238 (13)	H(1)···H(4)^ii	3.30 (3)
C(1)···O(3)^i	3.3630 (14)	H(1)···H(10)^i	2.76 (3)
C(2)···O(2)^vi	3.5759 (14)	H(1)···H(12)^ii	3.00 (3)
C(8)···O(1)^viii	3.3003 (15)	H(1)···H(14)^ii	3.02 (3)
C(8)···O(2)^vii	3.4044 (15)	H(1)···H(15)^ii	2.71 (3)
C(8)···O(2)^ix	3.4798 (15)	H(2)···O(1)^vi	2.861 (14)
C(8)···O(2)^x	3.4977 (15)	H(2)···O(2)^vi	2.678 (14)
C(8)···O(3)^iii	3.4278 (14)	H(2)···C(1)^vi	2.958 (14)
O(1)···H(2)	2.582 (14)	H(2)···H(1)^vi	2.36 (3)
O(1)···H(3)	2.507 (15)	H(2)···H(5)^vi	2.77 (3)
O(1)···H(5)	2.94 (2)	H(2)···H(13)^v	3.09 (2)
O(2)···H(1)	2.267 (18)	H(2)···H(14)^ii	3.38 (2)
O(2)···H(2)	3.040 (14)	H(3)···C(5)^vi	3.561 (15)
O(2)···H(5)	2.79 (2)	H(3)···H(5)^vi	3.10 (3)
O(2)···H(12)	2.489 (16)	H(3)···H(6)^vi	3.16 (3)
O(3)···H(2)	2.489 (14)	H(3)···H(7)^vi	3.29 (3)
O(3)···H(9)	3.063 (19)	H(3)···H(8)^xiii	3.53 (3)
O(3)···H(10)	3.07 (2)	H(3)···H(11)^xiv	3.52 (3)
O(3)···H(12)	3.039 (16)	H(4)···O(3)^iii	2.88 (2)
O(3)···H(13)	2.599 (17)	H(4)···C(6)^iii	2.95 (2)
O(3)···H(14)	2.626 (17)	H(4)···C(7)^iii	3.498 (19)
O(3)···H(15)	3.201 (15)	H(4)···H(1)^viii	3.30 (3)
N(1)···H(3)	3.338 (15)	H(4)···H(9)^iii	2.50 (3)
N(1)···H(4)	2.886 (19)	H(4)···H(10)^iii	2.63 (3)
N(1)···H(5)	3.19 (2)	H(4)···H(11)^iii	3.36 (3)
N(1)···H(9)	2.689 (19)	H(5)···O(1)^i	3.32 (2)
N(1)···H(10)	3.34 (2)	H(5)···O(3)^iii	3.60 (2)
N(1)···H(13)	3.028 (17)	H(5)···C(2)^i	3.50 (2)
N(1)···H(14)	3.068 (17)	H(5)···H(2)^i	2.77 (3)
N(1)···H(15)	2.501 (15)	H(5)···H(3)^i	3.10 (3)
C(1)···H(3)	2.654 (14)	H(5)···H(9)^iii	3.14 (3)
C(1)···H(4)	3.42 (2)	H(5)···H(10)^i	3.42 (3)
C(1)···H(5)	2.47 (2)	H(5)···H(14)^iii	3.32 (3)
C(1)···H(12)	2.581 (16)	H(6)···C(5)^xi	3.17 (3)
C(2)···H(1)	3.112 (19)	H(6)···C(6)^iii	3.14 (3)
C(2)···H(4)	2.83 (2)	H(6)···H(3)^i	3.16 (3)
C(2)···H(5)	2.62 (2)	H(6)···H(6)^xi	2.46 (3)
C(2)···H(9)	2.71 (2)	H(6)···H(7)^xi	3.15 (4)
C(2)···H(10)	2.74 (2)	H(6)···H(7)^xii	3.52 (4)
C(2)···H(11)	3.40 (2)	H(6)···H(8)^xi	3.42 (4)
C(3)···H(6)	3.39 (3)	H(6)···H(9)^iii	2.66 (3)
C(3)···H(7)	2.85 (3)	H(6)···H(10)^iii	3.42 (3)
C(3)···H(8)	2.75 (3)	H(6)···H(11)^iii	2.89 (3)
C(3)···H(12)	2.949 (15)	H(7)···C(5)^xiii	3.27 (3)
C(4)···H(2)	3.370 (14)	H(7)···H(3)^i	3.29 (3)
C(4)···H(9)	2.72 (2)	H(7)···H(6)^xi	3.15 (4)
C(4)···H(10)	3.46 (3)	H(7)···H(6)^xiii	3.52 (4)
C(4)···H(11)	2.77 (2)	H(7)···H(8)^xiii	2.36 (4)
C(4)···H(12)	3.058 (15)	H(7)···H(10)^i	3.19 (4)
C(5)···H(3)	2.673 (15)	H(7)···H(10)^xiv	3.49 (4)
C(5)···H(9)	3.532 (19)	H(7)···H(11)^xiv	3.48 (3)
C(5)···H(11)	2.89 (2)	H(7)···H(11)^xiii	2.97 (4)
C(6)···H(2)	2.690 (13)	H(8)···C(5)^xii	3.36 (3)
C(6)···H(4)	2.65 (2)	H(8)···C(6)^xiv	3.57 (3)
C(6)···H(5)	3.40 (2)	H(8)···H(3)^xii	3.53 (3)
C(6)···H(8)	2.86 (3)	H(8)···H(6)^xi	3.42 (4)
C(6)···H(12)	3.579 (15)	H(8)···H(7)^xii	2.36 (4)
C(7)···H(2)	2.530 (13)	H(8)···H(9)^iii	3.58 (3)
C(7)···H(9)	2.955 (19)	H(8)···H(10)^iii	3.59 (4)
C(7)···H(10)	3.50 (2)	H(8)···H(10)^xiv	3.01 (3)
C(8)···H(12)	2.469 (16)	H(8)···H(11)^iii	3.48 (4)
H(1)···H(2)	3.39 (3)	H(8)···H(11)^xiv	3.10 (4)
H(1)···H(3)	3.28 (3)	H(9)···O(1)^viii	3.53 (2)
H(1)···H(5)	3.27 (3)	H(9)···C(4)^vii	3.09 (2)
H(2)···H(3)	2.326 (19)	H(9)···C(5)^vii	3.23 (2)
H(2)···H(5)	3.53 (3)	H(9)···H(4)^vii	2.50 (3)
H(2)···H(9)	3.00 (3)	H(9)···H(5)^vii	3.14 (3)
H(2)···H(10)	2.51 (3)	H(9)···H(6)^vii	2.66 (3)
H(2)···H(11)	3.60 (3)	H(9)···H(8)^vii	3.58 (3)
H(2)···H(12)	2.76 (2)	H(10)···O(1)^vi	3.01 (2)
H(3)···H(4)	2.86 (3)	H(10)···C(4)^vii	3.50 (2)
H(3)···H(5)	2.47 (3)	H(10)···H(1)^vi	2.76 (3)
H(3)···H(6)	3.56 (3)	H(10)···H(4)^vii	2.63 (3)
H(3)···H(7)	2.58 (3)	H(10)···H(5)^vi	3.42 (3)
H(3)···H(8)	2.92 (3)	H(10)···H(6)^vii	3.42 (3)
H(3)···H(9)	2.86 (3)	H(10)···H(7)^vi	3.19 (4)
H(3)···H(10)	2.40 (3)	H(10)···H(7)^xiv	3.49 (4)
H(3)···H(11)	2.40 (3)	H(10)···H(8)^vii	3.59 (4)
H(4)···H(6)	2.38 (3)	H(10)···H(8)^xiv	3.01 (3)
H(4)···H(7)	2.93 (4)	H(10)···H(11)^xiv	3.48 (3)
H(4)···H(8)	2.36 (3)	H(11)···C(5)^vii	3.51 (2)
H(4)···H(9)	2.45 (3)	H(11)···C(6)^xiv	3.38 (2)
H(4)···H(11)	2.92 (3)	H(11)···H(3)^xiv	3.52 (3)
H(4)···H(12)	2.71 (3)	H(11)···H(4)^vii	3.36 (3)
H(5)···H(6)	2.35 (3)	H(11)···H(6)^vii	2.89 (3)
H(5)···H(7)	2.49 (3)	H(11)···H(7)^xiv	3.48 (3)
H(5)···H(8)	2.89 (3)	H(11)···H(7)^xii	2.97 (4)
H(5)···H(9)	3.57 (3)	H(11)···H(8)^vii	3.48 (4)
H(5)···H(12)	3.00 (3)	H(11)···H(8)^xiv	3.10 (4)
H(7)···H(11)	3.26 (4)	H(11)···H(10)^xiv	3.48 (3)
H(8)···H(9)	3.20 (3)	H(11)···H(11)^xiv	2.54 (3)
H(8)···H(11)	2.31 (4)	H(12)···O(1)^viii	3.545 (16)
H(9)···H(12)	3.15 (3)	H(12)···O(3)^iii	2.237 (16)
H(12)···H(13)	3.14 (3)	H(12)···C(7)^iii	3.079 (16)
H(12)···H(14)	3.15 (3)	H(12)···C(8)^iii	3.279 (16)
H(12)···H(15)	2.19 (3)	H(12)···H(1)^viii	3.00 (3)
O(1)···H(2)^i	2.861 (14)	H(12)···H(13)^iii	3.25 (3)
O(1)···H(5)^vi	3.32 (2)	H(12)···H(14)^iii	2.88 (3)
O(1)···H(9)^ii	3.53 (2)	H(12)···H(15)^v	3.35 (2)
O(1)···H(10)^i	3.01 (2)	H(13)···O(2)^vii	3.531 (17)
O(1)···H(12)^ii	3.545 (16)	H(13)···O(2)^ix	2.548 (17)
O(1)···H(14)^ii	2.899 (16)	H(13)···O(2)^x	3.383 (16)
O(1)···H(15)^ii	3.060 (15)	H(13)···O(3)^x	3.384 (17)
O(2)···H(2)^i	2.678 (14)	H(13)···N(1)^x	3.274 (17)
O(2)···H(13)^iii	3.531 (17)	H(13)···C(1)^x	3.363 (17)
O(2)···H(13)^iv	2.548 (17)	H(13)···C(2)^x	3.428 (17)
O(2)···H(13)^v	3.383 (16)	H(13)···C(7)^x	3.221 (17)
O(2)···H(14)^iii	2.504 (17)	H(13)···C(8)^v	3.511 (17)
O(2)···H(15)^ii	3.589 (16)	H(13)···H(2)^x	3.09 (2)
O(2)···H(15)^v	2.762 (15)	H(13)···H(12)^vii	3.25 (3)
O(3)···H(1)^vi	1.752 (19)	H(13)···H(13)^x	3.53 (3)
O(3)···H(4)^vii	2.88 (2)	H(13)···H(13)^v	3.53 (3)
O(3)···H(5)^vii	3.60 (2)	H(13)···H(14)^v	2.83 (3)
O(3)···H(12)^vii	2.237 (16)	H(13)···H(15)^vii	3.47 (3)
O(3)···H(13)^v	3.384 (17)	H(14)···O(1)^viii	2.899 (16)
O(3)···H(15)^vii	2.661 (15)	H(14)···O(2)^vii	2.504 (17)
N(1)···H(1)^viii	3.452 (19)	H(14)···C(1)^viii	3.240 (17)
N(1)···H(1)^vi	3.391 (19)	H(14)···C(1)^vii	3.482 (16)
N(1)···H(13)^v	3.274 (17)	H(14)···C(7)^x	3.430 (16)
N(1)···H(15)^v	3.382 (15)	H(14)···C(8)^x	3.428 (17)
C(1)···H(2)^i	2.958 (14)	H(14)···H(1)^viii	3.02 (3)
C(1)···H(13)^v	3.363 (17)	H(14)···H(2)^viii	3.38 (2)
C(1)···H(14)^ii	3.240 (17)	H(14)···H(5)^vii	3.32 (3)
C(1)···H(14)^iii	3.482 (16)	H(14)···H(12)^vii	2.88 (3)
C(1)···H(15)^ii	3.496 (16)	H(14)···H(13)^x	2.83 (3)
C(1)···H(15)^v	3.319 (15)	H(15)···O(1)^viii	3.060 (15)
C(2)···H(1)^vi	3.192 (19)	H(15)···O(2)^viii	3.589 (16)
C(2)···H(5)^vi	3.50 (2)	H(15)···O(2)^x	2.762 (15)
C(2)···H(13)^v	3.428 (17)	H(15)···O(3)^iii	2.661 (15)
C(4)···H(9)^iii	3.09 (2)	H(15)···N(1)^x	3.382 (15)
C(4)···H(10)^iii	3.50 (2)	H(15)···C(1)^viii	3.496 (16)
C(5)···H(3)^i	3.561 (15)	H(15)···C(1)^x	3.319 (15)
C(5)···H(6)^xi	3.17 (3)	H(15)···C(7)^iii	3.589 (15)
C(5)···H(7)^xii	3.27 (3)	H(15)···H(1)^viii	2.71 (3)
C(5)···H(8)^xiii	3.36 (3)	H(15)···H(12)^x	3.35 (2)
C(5)···H(9)^iii	3.23 (2)	H(15)···H(13)^iii	3.47 (3)
C(2)—N(1)—C(7)	124.57 (9)	C(3)—C(4)—H(4)	108.4 (12)
O(1)—C(1)—O(2)	124.25 (10)	C(3)—C(4)—H(5)	110.0 (11)
O(1)—C(1)—C(2)	111.56 (9)	C(5)—C(4)—H(4)	108.2 (11)
O(2)—C(1)—C(2)	124.14 (10)	C(5)—C(4)—H(5)	109.0 (11)
N(1)—C(2)—C(1)	108.44 (9)	H(4)—C(4)—H(5)	107.2 (16)
N(1)—C(2)—C(3)	114.64 (9)	C(4)—C(5)—H(6)	110.3 (12)
C(1)—C(2)—C(3)	109.23 (9)	C(4)—C(5)—H(7)	114.4 (14)
C(2)—C(3)—C(4)	111.04 (10)	C(4)—C(5)—H(8)	108.7 (14)
C(2)—C(3)—C(6)	110.30 (10)	H(6)—C(5)—H(7)	104.2 (19)
C(4)—C(3)—C(6)	112.36 (12)	H(6)—C(5)—H(8)	112 (2)
C(3)—C(4)—C(5)	113.82 (13)	H(7)—C(5)—H(8)	107 (2)
O(3)—C(7)—N(1)	123.38 (10)	C(3)—C(6)—H(9)	107.0 (11)
O(3)—C(7)—C(8)	119.75 (10)	C(3)—C(6)—H(10)	110.2 (12)
N(1)—C(7)—C(8)	116.87 (10)	C(3)—C(6)—H(11)	111.1 (12)
C(1)—O(1)—H(1)	106.8 (12)	H(9)—C(6)—H(10)	112.3 (16)
C(2)—N(1)—H(12)	119.3 (10)	H(9)—C(6)—H(11)	110.3 (16)
C(7)—N(1)—H(12)	115.9 (10)	H(10)—C(6)—H(11)	105.9 (16)
N(1)—C(2)—H(2)	107.0 (8)	C(7)—C(8)—H(13)	107.5 (10)
C(1)—C(2)—H(2)	108.9 (8)	C(7)—C(8)—H(14)	109.6 (10)
C(3)—C(2)—H(2)	108.4 (8)	C(7)—C(8)—H(15)	112.4 (9)
C(2)—C(3)—H(3)	106.2 (9)	H(13)—C(8)—H(14)	105.0 (14)
C(4)—C(3)—H(3)	108.1 (8)	H(13)—C(8)—H(15)	111.2 (13)
C(6)—C(3)—H(3)	108.5 (9)	H(14)—C(8)—H(15)	110.8 (13)
C(2)—N(1)—C(7)—O(3)	−7.67 (17)	O(2)—C(1)—C(2)—C(3)	118.70 (10)
C(2)—N(1)—C(7)—C(8)	171.78 (9)	N(1)—C(2)—C(3)—C(4)	64.68 (11)
C(7)—N(1)—C(2)—C(1)	−133.91 (10)	N(1)—C(2)—C(3)—C(6)	−60.55 (12)
C(7)—N(1)—C(2)—C(3)	103.75 (11)	C(1)—C(2)—C(3)—C(4)	−57.23 (11)
O(1)—C(1)—C(2)—N(1)	175.58 (8)	C(1)—C(2)—C(3)—C(6)	177.54 (8)
O(1)—C(1)—C(2)—C(3)	−58.84 (11)	C(2)—C(3)—C(4)—C(5)	164.66 (9)
O(2)—C(1)—C(2)—N(1)	−6.87 (14)	C(6)—C(3)—C(4)—C(5)	−71.27 (14)

Symmetry codes: (i) −x+5/2, y+1/2, z; (ii) x+1, y, z; (iii) −x+3/2, y+1/2, z; (iv) −x+2, y+1/2, −z+3/2; (v) x+1/2, y, −z+3/2; (vi) −x+5/2, y−1/2, z; (vii) −x+3/2, y−1/2, z; (viii) x−1, y, z; (ix) −x+2, y−1/2, −z+3/2; (x) x−1/2, y, −z+3/2; (xi) −x+2, −y+1, −z+1; (xii) x−1/2, −y+1/2, −z+1; (xiii) x+1/2, −y+1/2, −z+1; (xiv) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O(1)—H(1)···O(3)^i	0.87 (2)	1.752 (19)	2.6178 (12)	169.5 (18)
N(1)—H(12)···O(2)	0.887 (19)	2.489 (16)	2.6986 (13)	93.9 (11)
N(1)—H(12)···O(3)^iii	0.887 (16)	2.237 (16)	3.0238 (13)	147.4 (14)

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

(Ac-DL-aIle)

Crystal data

C8H15NO3	Dx = 1.160 Mg m^−3
Mr = 173.21	Melting point = 169–172 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 15102 reflections
a = 11.6067 (6) Å	θ = 3.1–27.5°
b = 12.8312 (5) Å	µ = 0.09 mm^−1
c = 13.3226 (5) Å	T = 123 K
V = 1984.10 (14) Å^3	Prism, colorless
Z = 8	0.19 × 0.19 × 0.10 mm
F(000) = 752.00

Data collection

Rigaku R-AXIS RAPID diffractometer	2073 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.020
ω scans	θmax = 27.5°
Absorption correction: multi-scan ABSCOR (Rigaku, 1995)	h = −15→15
Tmin = 0.847, Tmax = 0.991	k = −16→16
18159 measured reflections	l = −17→17
2273 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	Only H-atom coordinates refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0533P)^2 + 0.5339P] where P = (Fo^2 + 2Fc^2)/3
2273 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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

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

	x	y	z	Uiso*/Ueq
O1	0.18921 (6)	0.03805 (6)	0.44908 (6)	0.02777 (19)
O2	0.32409 (6)	0.05948 (6)	0.78215 (5)	0.02527 (18)
O10	0.36336 (6)	−0.03573 (6)	0.46237 (5)	0.0286 (2)
N9	0.41309 (7)	0.07249 (6)	0.63229 (6)	0.01906 (19)
C2	0.29148 (8)	0.02637 (8)	0.49057 (7)	0.0206 (2)
C3	0.30870 (8)	0.10077 (7)	0.57840 (7)	0.0194 (2)
C4	0.52444 (9)	0.01498 (10)	0.77553 (8)	0.0297 (3)
C5	0.31017 (10)	0.21531 (9)	0.54170 (9)	0.0338 (3)
C6	0.31429 (15)	0.29051 (10)	0.63023 (13)	0.0533 (5)
C7	0.20950 (19)	0.29089 (14)	0.69605 (14)	0.0664 (6)
C8	0.40999 (14)	0.23326 (14)	0.46747 (15)	0.0585 (5)
C11	0.41291 (8)	0.05116 (7)	0.73041 (7)	0.0190 (2)
H12	0.2184 (19)	0.3468 (19)	0.751 (2)	0.092 (7)*
H13	0.1384 (18)	0.3058 (17)	0.6526 (16)	0.075 (6)*
H14	0.1991 (17)	0.2244 (17)	0.7313 (16)	0.070 (6)*
H15	0.3844 (15)	0.2752 (14)	0.6714 (13)	0.051 (5)*
H16	0.3283 (14)	0.3611 (16)	0.5996 (14)	0.062 (5)*
H17	0.2373 (12)	0.2258 (11)	0.5054 (12)	0.035 (4)*
H18	0.4835 (19)	0.2265 (15)	0.5024 (16)	0.076 (6)*
H19	0.4063 (19)	0.3029 (19)	0.4404 (16)	0.082 (7)*
H20	0.410 (2)	0.190 (2)	0.404 (2)	0.097 (8)*
H21	0.1831 (15)	0.0003 (15)	0.3911 (15)	0.060 (5)*
H22	0.2462 (10)	0.0906 (9)	0.6227 (8)	0.016 (3)*
H23	0.4750 (12)	0.0607 (10)	0.5999 (10)	0.027 (3)*
H24	0.5892 (14)	0.0300 (12)	0.7347 (12)	0.044 (4)*
H25	0.5367 (15)	0.0443 (13)	0.8383 (14)	0.050 (5)*
H26	0.5163 (18)	−0.0585 (17)	0.7852 (14)	0.072 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0213 (4)	0.0388 (5)	0.0232 (4)	0.0038 (3)	−0.0061 (3)	−0.0077 (3)
O2	0.0212 (4)	0.0353 (4)	0.0193 (4)	0.0020 (3)	0.0033 (3)	0.0034 (3)
O10	0.0201 (4)	0.0407 (5)	0.0249 (4)	0.0035 (3)	0.0011 (3)	−0.0086 (3)
N9	0.0148 (4)	0.0256 (4)	0.0168 (4)	0.0010 (3)	0.0005 (3)	0.0007 (3)
C2	0.0171 (5)	0.0287 (5)	0.0160 (4)	−0.0022 (4)	0.0015 (4)	0.0021 (4)
C3	0.0163 (4)	0.0236 (5)	0.0184 (5)	−0.0002 (4)	−0.0015 (4)	0.0010 (4)
C4	0.0221 (5)	0.0436 (7)	0.0234 (5)	0.0057 (5)	−0.0039 (4)	0.0031 (5)
C5	0.0345 (6)	0.0251 (5)	0.0417 (7)	−0.0022 (4)	−0.0161 (5)	0.0078 (5)
C6	0.0688 (10)	0.0226 (6)	0.0685 (10)	0.0059 (6)	−0.0424 (8)	−0.0056 (6)
C7	0.0897 (13)	0.0479 (9)	0.0615 (10)	0.0337 (9)	−0.0300 (10)	−0.0280 (8)
C8	0.0500 (9)	0.0552 (9)	0.0702 (11)	−0.0150 (7)	−0.0077 (8)	0.0382 (9)
C11	0.0191 (5)	0.0194 (4)	0.0185 (5)	−0.0007 (3)	−0.0008 (4)	−0.0001 (4)

Geometric parameters (Å, º)

O1—C2	1.3180 (12)	C3—H22	0.944 (12)
O2—C11	1.2447 (12)	C4—H24	0.948 (16)
O10—C2	1.2133 (13)	C4—H25	0.928 (18)
N9—C3	1.4544 (13)	C4—H26	0.96 (2)
N9—C11	1.3356 (13)	C5—H17	0.984 (14)
C2—C3	1.5233 (14)	C6—H15	1.000 (17)
C3—C5	1.5490 (15)	C6—H16	1.01 (2)
C4—C11	1.5009 (15)	C7—H12	1.03 (3)
C5—C6	1.525 (2)	C7—H13	1.03 (2)
C5—C8	1.541 (3)	C7—H14	0.98 (3)
C6—C7	1.499 (3)	C8—H18	0.98 (3)
O1—H21	0.91 (2)	C8—H19	0.97 (3)
N9—H23	0.851 (14)	C8—H20	1.01 (3)
O1···N9	3.5924 (11)	N9···H13^v	3.48 (2)
O1···C5	2.9439 (14)	C2···H16^v	2.923 (19)
O1···C8	3.5917 (19)	C2···H23^iii	3.170 (14)
O2···C3	2.7715 (12)	C2···H24^iii	3.383 (16)
O2···C6	3.5912 (17)	C3···H16^v	3.474 (19)
O2···C7	3.450 (2)	C3···H25^vi	3.424 (17)
O10···N9	2.7177 (11)	C4···H12^v	3.56 (3)
O10···C5	3.4458 (14)	C4···H14^viii	3.37 (2)
O10···C8	3.494 (2)	C4···H15^ix	3.329 (17)
N9···C6	3.0235 (16)	C4···H16^ix	3.096 (19)
N9···C8	3.013 (2)	C4···H19^vii	3.49 (3)
C2···C8	3.006 (2)	C4···H21^ii	2.865 (18)
C2···C11	3.5068 (14)	C4···H22^viii	3.067 (12)
C3···C7	3.120 (2)	C6···H26^x	2.98 (2)
C5···C11	3.4898 (15)	C7···H26^xi	3.47 (2)
C6···C11	3.5388 (17)	C8···H13^xii	3.14 (2)
O1···O2^i	2.5565 (11)	C11···H12^v	3.04 (3)
O1···C4^i	3.4581 (13)	C11···H13^v	3.37 (2)
O1···C11^i	3.3470 (13)	C11···H19^vii	3.37 (3)
O2···O1^ii	2.5565 (11)	C11···H21^ii	2.50 (2)
O2···O10^ii	3.2544 (10)	H12···O1^vii	3.04 (3)
O2···C2^ii	3.2746 (12)	H12···O2^xi	2.80 (3)
O10···O2^i	3.2544 (10)	H12···C4^xi	3.56 (3)
O10···O10^iii	3.4506 (10)	H12···C11^xi	3.04 (3)
O10···N9^iii	2.9232 (11)	H12···H17^vii	3.52 (3)
O10···C4^iii	3.4369 (13)	H12···H20^vii	3.06 (4)
N9···O10^iii	2.9232 (11)	H12···H21^vii	2.74 (4)
C2···O2^i	3.2746 (12)	H12···H22^xi	3.59 (3)
C4···O1^ii	3.4581 (13)	H12···H24^x	3.25 (3)
C4···O10^iii	3.4369 (13)	H12···H26^xi	3.02 (3)
C11···O1^ii	3.3470 (13)	H12···H26^x	3.35 (3)
O1···H17	2.584 (14)	H13···O10^xi	3.25 (2)
O1···H20	3.28 (3)	H13···N9^xi	3.48 (2)
O1···H22	2.498 (11)	H13···C8^xiii	3.14 (2)
O2···H14	2.65 (2)	H13···C11^xi	3.37 (2)
O2···H15	3.215 (17)	H13···H18^xiii	2.77 (3)
O2···H22	2.343 (11)	H13···H19^xiii	3.28 (3)
O2···H23	2.994 (14)	H13···H20^xiii	2.75 (4)
O2···H24	3.164 (16)	H13···H23^xi	3.59 (3)
O2···H25	2.586 (17)	H13···H25^vi	3.56 (3)
O2···H26	2.70 (2)	H13···H26^xi	3.06 (3)
O10···H20	3.05 (3)	H14···C4^vi	3.37 (2)
O10···H21	2.344 (18)	H14···H20^vii	3.54 (4)
O10···H22	3.006 (11)	H14···H24^vi	2.84 (3)
O10···H23	2.562 (14)	H14···H25^vi	3.12 (3)
N9···H14	3.42 (2)	H15···C4^x	3.329 (17)
N9···H15	2.674 (17)	H15···H20^vii	3.14 (3)
N9···H17	3.300 (14)	H15···H24^x	3.51 (3)
N9···H18	2.75 (2)	H15···H25^x	3.57 (3)
N9···H20	3.40 (3)	H15···H26^x	2.49 (3)
N9···H24	2.517 (16)	H16···O1^xi	3.036 (19)
N9···H25	3.118 (18)	H16···O10^xi	3.169 (18)
N9···H26	2.90 (2)	H16···C2^xi	2.923 (19)
C2···H17	2.642 (14)	H16···C3^xi	3.474 (19)
C2···H18	3.40 (2)	H16···C4^x	3.096 (19)
C2···H20	2.77 (3)	H16···H21^xi	3.31 (3)
C2···H23	2.617 (14)	H16···H22^xi	3.08 (3)
C3···H13	3.44 (2)	H16···H24^x	3.24 (3)
C3···H14	2.88 (2)	H16···H25^x	2.94 (3)
C3···H15	2.705 (17)	H16···H26^x	2.58 (3)
C3···H16	3.36 (2)	H17···O10^xi	3.325 (14)
C3···H18	2.78 (2)	H17···H12^iv	3.52 (3)
C3···H19	3.38 (3)	H17···H18^xiii	3.01 (3)
C3···H20	2.85 (3)	H18···O10^iii	3.06 (2)
C3···H21	3.165 (19)	H18···H13^xii	2.77 (3)
C4···H23	2.480 (14)	H18···H17^xii	3.01 (3)
C5···H12	3.43 (3)	H19···O1^xi	3.22 (3)
C5···H13	2.74 (2)	H19···O2^iv	2.91 (3)
C5···H14	2.84 (2)	H19···C4^iv	3.49 (3)
C5···H23	2.862 (14)	H19···C11^iv	3.37 (3)
C6···H18	2.73 (3)	H19···H13^xii	3.28 (3)
C6···H19	2.75 (3)	H19···H21^xi	2.81 (3)
C6···H20	3.47 (3)	H19···H25^iv	2.83 (3)
C6···H22	2.686 (12)	H20···H12^iv	3.06 (4)
C6···H23	3.512 (13)	H20···H13^xii	2.75 (4)
C7···H17	2.693 (15)	H20···H14^iv	3.54 (4)
C7···H22	2.782 (12)	H20···H15^iv	3.14 (3)
C8···H15	2.785 (17)	H20···H23^iii	3.48 (3)
C8···H16	2.586 (19)	H20···H24^iii	3.37 (3)
C8···H22	3.352 (12)	H20···H26^iii	3.15 (4)
C8···H23	2.929 (13)	H21···O2^i	1.64 (2)
C11···H14	3.33 (2)	H21···C4^i	2.865 (18)
C11···H15	2.999 (17)	H21···C11^i	2.50 (2)
C11···H22	2.462 (12)	H21···H12^iv	2.74 (4)
H12···H15	2.38 (3)	H21···H16^v	3.31 (3)
H12···H16	2.39 (3)	H21···H19^v	2.81 (3)
H13···H15	2.89 (3)	H21···H24^iii	3.15 (3)
H13···H16	2.42 (3)	H21···H25^i	2.71 (3)
H13···H17	2.49 (3)	H21···H26^i	2.81 (3)
H13···H22	3.06 (3)	H22···C4^vi	3.067 (12)
H14···H15	2.39 (3)	H22···H12^v	3.59 (3)
H14···H16	2.90 (3)	H22···H16^v	3.08 (3)
H14···H17	3.04 (3)	H22···H24^vi	2.75 (2)
H14···H22	2.31 (3)	H22···H25^vi	2.56 (2)
H15···H17	2.86 (3)	H22···H26^vi	3.51 (3)
H15···H18	2.60 (3)	H23···O10^iii	2.077 (14)
H15···H19	3.11 (3)	H23···C2^iii	3.170 (14)
H15···H22	2.93 (2)	H23···H13^v	3.59 (3)
H15···H23	3.10 (3)	H23···H20^iii	3.48 (3)
H16···H17	2.39 (3)	H23···H23^iii	3.138 (19)
H16···H18	2.81 (3)	H24···O2^viii	2.761 (16)
H16···H19	2.42 (3)	H24···O10^iii	2.683 (17)
H16···H20	3.54 (4)	H24···C2^iii	3.383 (16)
H17···H18	2.86 (3)	H24···H12^ix	3.25 (3)
H17···H19	2.36 (3)	H24···H14^viii	2.84 (3)
H17···H20	2.47 (3)	H24···H15^ix	3.51 (3)
H17···H21	3.33 (3)	H24···H16^ix	3.24 (3)
H17···H22	2.336 (18)	H24···H20^iii	3.37 (3)
H18···H23	2.49 (3)	H24···H21^iii	3.15 (3)
H20···H21	3.60 (3)	H24···H22^viii	2.75 (2)
H20···H23	3.19 (3)	H25···O1^ii	3.189 (17)
H21···H22	3.38 (3)	H25···O1^viii	3.341 (18)
H22···H23	2.700 (18)	H25···C3^viii	3.424 (17)
H23···H24	2.27 (2)	H25···H13^viii	3.56 (3)
H23···H25	3.26 (3)	H25···H14^viii	3.12 (3)
H23···H26	2.94 (3)	H25···H15^ix	3.57 (3)
O1···H12^iv	3.04 (3)	H25···H16^ix	2.94 (3)
O1···H16^v	3.036 (19)	H25···H19^vii	2.83 (3)
O1···H19^v	3.22 (3)	H25···H21^ii	2.71 (3)
O1···H25^i	3.189 (17)	H25···H22^viii	2.56 (2)
O1···H25^vi	3.341 (18)	H26···O1^ii	3.24 (2)
O1···H26^i	3.24 (2)	H26···C6^ix	2.98 (2)
O2···H12^v	2.80 (3)	H26···C7^v	3.47 (2)
O2···H19^vii	2.91 (3)	H26···H12^v	3.02 (3)
O2···H21^ii	1.64 (2)	H26···H12^ix	3.35 (3)
O2···H24^vi	2.761 (16)	H26···H13^v	3.06 (3)
O10···H13^v	3.25 (2)	H26···H15^ix	2.49 (3)
O10···H16^v	3.169 (18)	H26···H16^ix	2.58 (3)
O10···H17^v	3.325 (14)	H26···H20^iii	3.15 (4)
O10···H18^iii	3.06 (2)	H26···H21^ii	2.81 (3)
O10···H23^iii	2.077 (14)	H26···H22^viii	3.51 (3)
O10···H24^iii	2.683 (17)
C3—N9—C11	122.21 (8)	H24—C4—H25	108.3 (15)
O1—C2—O10	124.34 (9)	H24—C4—H26	110.9 (16)
O1—C2—C3	111.66 (9)	H25—C4—H26	107.1 (16)
O10—C2—C3	124.00 (9)	C3—C5—H17	106.0 (9)
N9—C3—C2	109.40 (8)	C6—C5—H17	108.7 (9)
N9—C3—C5	112.54 (8)	C8—C5—H17	108.1 (9)
C2—C3—C5	110.71 (9)	C5—C6—H15	109.0 (10)
C3—C5—C6	110.89 (10)	C5—C6—H16	105.1 (11)
C3—C5—C8	110.66 (11)	C7—C6—H15	109.9 (10)
C6—C5—C8	112.23 (12)	C7—C6—H16	111.4 (10)
C5—C6—C7	115.41 (14)	H15—C6—H16	105.5 (14)
O2—C11—N9	121.72 (9)	C6—C7—H12	109.6 (13)
O2—C11—C4	121.27 (9)	C6—C7—H13	108.8 (12)
N9—C11—C4	117.00 (9)	C6—C7—H14	112.1 (12)
C2—O1—H21	111.4 (11)	H12—C7—H13	110.6 (18)
C3—N9—H23	119.8 (9)	H12—C7—H14	106.2 (19)
C11—N9—H23	117.5 (9)	H13—C7—H14	109.5 (17)
N9—C3—H22	107.3 (7)	C5—C8—H18	109.8 (13)
C2—C3—H22	107.0 (7)	C5—C8—H19	110.2 (13)
C5—C3—H22	109.7 (7)	C5—C8—H20	117.4 (14)
C11—C4—H24	113.0 (10)	H18—C8—H19	107.4 (18)
C11—C4—H25	111.6 (11)	H18—C8—H20	110.2 (19)
C11—C4—H26	105.9 (13)	H19—C8—H20	101 (2)
C3—N9—C11—O2	−3.69 (13)	O10—C2—C3—C5	114.38 (10)
C3—N9—C11—C4	175.39 (7)	N9—C3—C5—C6	−63.36 (10)
C11—N9—C3—C2	−123.99 (9)	N9—C3—C5—C8	61.86 (11)
C11—N9—C3—C5	112.50 (9)	C2—C3—C5—C6	173.86 (7)
O1—C2—C3—N9	169.94 (7)	C2—C3—C5—C8	−60.92 (10)
O1—C2—C3—C5	−65.48 (10)	C3—C5—C6—C7	−65.98 (14)
O10—C2—C3—N9	−10.21 (13)	C8—C5—C6—C7	169.69 (11)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H21···O2^i	0.92 (2)	1.64 (2)	2.5565 (11)	175.5 (19)
N9—H23···O10	0.852 (14)	2.562 (14)	2.7177 (11)	91.3 (10)
N9—H23···O10^iii	0.852 (14)	2.077 (14)	2.9232 (11)	172.8 (13)

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

(Ac-DL-IleNH3)

Crystal data

C8H18N2O3	F(000) = 416.00
Mr = 190.24	Dx = 1.164 Mg m^−3
Monoclinic, P21/n	Melting point = 133–135 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.907 (4) Å	Cell parameters from 1083 reflections
b = 5.843 (3) Å	θ = 8.2–27.4°
c = 23.633 (10) Å	µ = 0.09 mm^−1
β = 96.126 (8)°	T = 123 K
V = 1085.5 (8) Å^3	Platelet, colorless
Z = 4	0.34 × 0.13 × 0.07 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2211 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.026
ω scans	θmax = 27.5°
Absorption correction: multi-scan ABSCOR (Rigaku, 1995)	h = −10→10
Tmin = 0.931, Tmax = 0.994	k = −7→7
10080 measured reflections	l = −30→30
2475 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	Only H-atom coordinates refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0506P)^2 + 0.3406P] where P = (Fo^2 + 2Fc^2)/3
2475 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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

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

	x	y	z	Uiso*/Ueq
O(2)	0.89245 (9)	0.18584 (13)	0.20210 (3)	0.01962 (18)
O(1)	0.91542 (10)	−0.12805 (12)	0.14981 (3)	0.02238 (19)
O(3)	1.30302 (10)	0.22752 (13)	0.17066 (3)	0.0240 (2)
N(1)	1.08180 (11)	0.43342 (15)	0.13010 (4)	0.01676 (19)
N(2)	0.91554 (12)	−0.37720 (16)	0.25050 (4)	0.0182 (2)
C(1)	0.92986 (12)	0.08429 (17)	0.15791 (4)	0.0158 (2)
C(2)	0.99203 (12)	0.22613 (17)	0.10925 (4)	0.0164 (2)
C(3)	0.84557 (14)	0.28604 (19)	0.06323 (5)	0.0226 (3)
C(4)	0.78276 (15)	0.0712 (3)	0.02941 (5)	0.0271 (3)
C(5)	0.68242 (19)	0.1286 (3)	−0.02759 (6)	0.0387 (4)
C(6)	0.69847 (16)	0.4105 (3)	0.08722 (6)	0.0311 (3)
C(7)	1.23479 (13)	0.41703 (17)	0.16026 (4)	0.0178 (3)
C(8)	1.31989 (15)	0.6377 (2)	0.18047 (5)	0.0246 (3)
H(2)	1.0755 (17)	0.129 (3)	0.0918 (6)	0.017 (3)*
H(3)	0.891 (2)	0.398 (3)	0.0329 (7)	0.033 (4)*
H(4)	0.709 (2)	−0.023 (3)	0.0534 (7)	0.035 (4)*
H(5)	0.882 (3)	−0.027 (3)	0.0230 (7)	0.039 (4)*
H(6)	0.579 (3)	0.219 (3)	−0.0215 (7)	0.038 (4)*
H(7)	0.644 (3)	−0.021 (4)	−0.0510 (8)	0.053 (5)*
H(8)	0.754 (3)	0.226 (4)	−0.0513 (8)	0.055 (5)*
H(9)	0.640 (2)	0.304 (3)	0.1122 (7)	0.036 (4)*
H(10)	0.609 (3)	0.460 (3)	0.0555 (8)	0.050 (5)*
H(11)	0.740 (3)	0.551 (3)	0.1091 (7)	0.045 (5)*
H(12)	1.034 (2)	0.569 (3)	0.1269 (6)	0.029 (4)*
H(13)	1.251 (2)	0.768 (3)	0.1699 (7)	0.035 (4)*
H(14)	1.345 (3)	0.631 (3)	0.2201 (9)	0.052 (5)*
H(15)	1.430 (3)	0.646 (3)	0.1658 (8)	0.049 (5)*
H(17)	0.9255 (19)	−0.524 (3)	0.2374 (7)	0.028 (4)*
H(16)	0.9098 (19)	−0.281 (3)	0.2209 (7)	0.033 (4)*
H(18)	1.009 (2)	−0.338 (3)	0.2773 (7)	0.032 (4)*
H(19)	0.816 (3)	−0.371 (3)	0.2669 (7)	0.035 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(2)	0.0217 (4)	0.0163 (4)	0.0214 (4)	−0.0022 (3)	0.0050 (3)	−0.0021 (3)
O(1)	0.0303 (5)	0.0118 (4)	0.0245 (4)	−0.0003 (3)	0.0005 (3)	−0.0002 (3)
O(3)	0.0214 (4)	0.0179 (4)	0.0309 (5)	0.0024 (3)	−0.0047 (3)	0.0003 (4)
N(1)	0.0172 (5)	0.0116 (4)	0.0212 (5)	−0.0004 (3)	0.0005 (4)	0.0012 (4)
N(2)	0.0183 (5)	0.0140 (5)	0.0224 (5)	−0.0005 (4)	0.0022 (4)	−0.0006 (4)
C(1)	0.0133 (5)	0.0135 (5)	0.0200 (5)	0.0007 (4)	−0.0020 (4)	0.0007 (4)
C(2)	0.0161 (5)	0.0137 (5)	0.0188 (5)	−0.0007 (4)	−0.0001 (4)	−0.0010 (4)
C(3)	0.0221 (6)	0.0220 (6)	0.0220 (5)	−0.0021 (4)	−0.0049 (4)	0.0036 (5)
C(4)	0.0248 (6)	0.0306 (6)	0.0250 (6)	0.0005 (5)	−0.0018 (5)	−0.0046 (5)
C(5)	0.0354 (8)	0.0526 (9)	0.0263 (7)	−0.0042 (7)	−0.0056 (6)	−0.0022 (6)
C(6)	0.0246 (6)	0.0263 (6)	0.0397 (7)	0.0072 (5)	−0.0088 (5)	−0.0053 (6)
C(7)	0.0178 (5)	0.0169 (5)	0.0187 (5)	−0.0015 (4)	0.0019 (4)	0.0003 (4)
C(8)	0.0222 (6)	0.0194 (6)	0.0308 (6)	−0.0040 (5)	−0.0032 (5)	−0.0014 (5)

Geometric parameters (Å, º)

O(2)—C(1)	1.2634 (13)	N(2)—H(19)	0.914 (18)
O(1)—C(1)	1.2587 (14)	C(2)—H(2)	0.993 (14)
O(3)—C(7)	1.2446 (14)	C(3)—H(3)	1.061 (16)
N(1)—C(2)	1.4625 (14)	C(4)—H(4)	1.017 (17)
N(1)—C(7)	1.3403 (14)	C(4)—H(5)	0.996 (17)
C(1)—C(2)	1.5400 (15)	C(5)—H(6)	1.000 (17)
C(2)—C(3)	1.5419 (15)	C(5)—H(7)	1.063 (19)
C(3)—C(4)	1.5415 (18)	C(5)—H(8)	1.01 (2)
C(3)—C(6)	1.5310 (19)	C(6)—H(9)	1.005 (17)
C(4)—C(5)	1.5259 (19)	C(6)—H(10)	1.014 (18)
C(7)—C(8)	1.5082 (16)	C(6)—H(11)	1.004 (17)
N(1)—H(12)	0.878 (16)	C(8)—H(13)	0.953 (16)
N(2)—H(17)	0.920 (16)	C(8)—H(14)	0.94 (2)
N(2)—H(16)	0.893 (17)	C(8)—H(15)	0.98 (2)
N(2)—H(18)	0.947 (15)
O(2)···O(3)	3.4153 (18)	C(8)···H(18)^xiv	3.453 (15)
O(2)···N(1)	2.7880 (14)	H(2)···C(4)^vii	3.393 (13)
O(2)···C(3)	3.315 (2)	H(2)···C(5)^vii	2.975 (14)
O(2)···C(6)	3.2494 (18)	H(2)···H(5)^vii	2.83 (2)
O(2)···C(7)	3.2711 (17)	H(2)···H(7)^vii	2.59 (3)
O(1)···N(1)	3.5833 (17)	H(2)···H(8)^vii	2.70 (3)
O(1)···C(3)	3.1787 (17)	H(2)···H(12)^iv	3.40 (2)
O(1)···C(4)	3.1489 (18)	H(2)···H(13)^iv	3.04 (2)
O(3)···C(1)	3.0506 (17)	H(3)···H(3)^ix	2.72 (3)
O(3)···C(2)	2.7186 (15)	H(3)···H(5)^i	3.37 (3)
N(1)···C(6)	3.094 (2)	H(3)···H(5)^vii	3.19 (3)
C(1)···C(4)	3.1349 (19)	H(3)···H(8)^ix	3.56 (3)
C(1)···C(6)	3.0198 (18)	H(4)···C(5)^xi	3.154 (16)
C(1)···C(7)	3.0930 (17)	H(4)···C(6)^iv	3.406 (16)
C(5)···C(6)	3.165 (3)	H(4)···H(6)^xi	2.59 (3)
O(2)···N(2)	3.4813 (18)	H(4)···H(7)^xi	2.80 (3)
O(2)···N(2)^i	2.7956 (16)	H(4)···H(10)^iv	3.12 (3)
O(2)···N(2)^ii	2.8112 (16)	H(4)···H(11)^iv	2.81 (3)
O(2)···C(8)^iii	3.4069 (17)	H(5)···C(2)^vii	3.575 (17)
O(1)···N(1)^iv	2.9399 (15)	H(5)···C(3)^vii	3.468 (18)
O(1)···N(2)	2.7895 (15)	H(5)···C(4)^vii	3.055 (18)
O(1)···C(6)^iv	3.4434 (18)	H(5)···C(5)^vii	3.485 (18)
O(1)···C(8)^iv	3.4829 (19)	H(5)···H(2)^vii	2.83 (2)
O(3)···N(2)^v	2.8130 (15)	H(5)···H(3)^iv	3.37 (3)
O(3)···C(8)^iv	3.455 (2)	H(5)···H(3)^vii	3.19 (3)
N(1)···O(1)^i	2.9399 (15)	H(5)···H(5)^vii	2.28 (3)
N(1)···N(2)^i	3.4420 (18)	H(5)···H(8)^vii	3.11 (3)
N(2)···O(2)^iv	2.7956 (16)	H(5)···H(11)^iv	3.46 (3)
N(2)···O(2)	3.4813 (18)	H(5)···H(12)^iv	3.52 (3)
N(2)···O(2)^vi	2.8112 (16)	H(6)···C(4)^xi	3.312 (17)
N(2)···O(1)	2.7895 (15)	H(6)···C(5)^xi	3.202 (18)
N(2)···O(3)^iii	2.8130 (15)	H(6)···C(6)^xii	3.341 (17)
N(2)···N(1)^iv	3.4420 (18)	H(6)···H(4)^xi	2.59 (3)
N(2)···C(1)	3.4820 (17)	H(6)···H(6)^xi	3.07 (3)
C(1)···N(2)	3.4820 (17)	H(6)···H(7)^xi	2.83 (3)
C(6)···O(1)^i	3.4434 (18)	H(6)···H(10)^xii	2.47 (3)
C(8)···O(2)^v	3.4069 (17)	H(6)···H(11)^xii	3.36 (3)
C(8)···O(1)^i	3.4829 (19)	H(6)···H(15)^ix	3.49 (3)
C(8)···O(3)^i	3.455 (2)	H(7)···O(3)^vii	3.142 (19)
O(2)···H(2)	3.132 (14)	H(7)···C(2)^vii	3.53 (2)
O(2)···H(9)	2.842 (15)	H(7)···C(4)^xi	3.48 (2)
O(2)···H(11)	3.204 (17)	H(7)···C(5)^xi	3.40 (2)
O(2)···H(12)	3.140 (16)	H(7)···C(6)^xi	3.571 (19)
O(1)···H(2)	2.471 (13)	H(7)···H(2)^vii	2.59 (3)
O(1)···H(4)	2.724 (15)	H(7)···H(4)^xi	2.80 (3)
O(1)···H(5)	3.038 (16)	H(7)···H(6)^xi	2.83 (3)
O(1)···H(9)	3.391 (16)	H(7)···H(7)^xi	3.50 (3)
O(3)···H(2)	2.515 (12)	H(7)···H(9)^xi	3.03 (3)
O(3)···H(12)	3.017 (15)	H(7)···H(10)^xi	3.25 (3)
O(3)···H(13)	3.185 (17)	H(7)···H(13)^ix	3.35 (3)
O(3)···H(14)	2.634 (18)	H(7)···H(15)^ix	3.49 (3)
O(3)···H(15)	2.649 (18)	H(8)···N(1)^ix	3.11 (2)
N(1)···H(3)	2.618 (15)	H(8)···C(7)^ix	3.32 (2)
N(1)···H(9)	3.557 (16)	H(8)···C(8)^ix	3.150 (19)
N(1)···H(11)	2.783 (17)	H(8)···H(2)^vii	2.70 (3)
N(1)···H(13)	2.497 (16)	H(8)···H(3)^ix	3.56 (3)
N(1)···H(14)	3.037 (19)	H(8)···H(5)^vii	3.11 (3)
N(1)···H(15)	3.058 (18)	H(8)···H(10)^xii	3.40 (3)
C(1)···H(3)	3.462 (15)	H(8)···H(12)^ix	2.84 (3)
C(1)···H(4)	2.934 (15)	H(8)···H(13)^ix	2.80 (3)
C(1)···H(5)	3.236 (16)	H(8)···H(15)^ix	3.03 (3)
C(1)···H(9)	2.747 (16)	H(9)···O(3)^xiii	3.159 (17)
C(1)···H(11)	3.262 (18)	H(9)···N(2)^ii	3.484 (17)
C(1)···H(12)	3.062 (16)	H(9)···C(7)^xiii	3.571 (17)
C(2)···H(4)	2.868 (16)	H(9)···H(7)^xi	3.03 (3)
C(2)···H(5)	2.592 (16)	H(9)···H(15)^xiii	2.96 (3)
C(2)···H(9)	2.831 (16)	H(9)···H(18)^ii	3.09 (3)
C(2)···H(10)	3.436 (18)	H(9)···H(19)^ii	3.02 (3)
C(2)···H(11)	2.752 (18)	H(10)···C(5)^xii	3.350 (18)
C(3)···H(6)	2.777 (16)	H(10)···H(4)^i	3.12 (3)
C(3)···H(7)	3.484 (18)	H(10)···H(6)^xii	2.47 (3)
C(3)···H(8)	2.748 (19)	H(10)···H(7)^xi	3.25 (3)
C(3)···H(12)	2.597 (15)	H(10)···H(8)^xii	3.40 (3)
C(4)···H(2)	2.630 (13)	H(10)···H(10)^xii	3.02 (3)
C(4)···H(9)	2.726 (17)	H(10)···H(15)^xiii	3.28 (3)
C(4)···H(10)	2.755 (19)	H(11)···O(1)^i	2.469 (17)
C(4)···H(11)	3.413 (18)	H(11)···N(2)^i	3.505 (17)
C(5)···H(3)	2.596 (15)	H(11)···C(1)^i	3.598 (18)
C(5)···H(9)	3.510 (17)	H(11)···H(4)^i	2.81 (3)
C(5)···H(10)	2.859 (19)	H(11)···H(5)^i	3.46 (3)
C(6)···H(2)	3.397 (13)	H(11)···H(6)^xii	3.36 (3)
C(6)···H(4)	2.662 (16)	H(11)···H(15)^xiii	2.96 (3)
C(6)···H(5)	3.378 (17)	H(11)···H(17)^i	3.26 (3)
C(6)···H(6)	2.868 (16)	H(11)···H(16)^i	3.00 (3)
C(6)···H(8)	3.52 (2)	H(12)···O(1)^i	2.101 (16)
C(6)···H(12)	2.873 (15)	H(12)···N(2)^i	3.178 (15)
C(7)···H(2)	2.570 (13)	H(12)···C(1)^i	3.226 (16)
C(8)···H(12)	2.501 (15)	H(12)···H(2)^i	3.40 (2)
H(2)···H(3)	2.469 (19)	H(12)···H(5)^i	3.52 (3)
H(2)···H(4)	3.07 (2)	H(12)···H(8)^ix	2.84 (3)
H(2)···H(5)	2.30 (2)	H(12)···H(17)^i	2.89 (3)
H(2)···H(12)	2.73 (2)	H(12)···H(16)^i	2.67 (3)
H(3)···H(4)	2.92 (3)	H(13)···O(1)^i	2.716 (16)
H(3)···H(5)	2.49 (3)	H(13)···O(3)^i	2.715 (17)
H(3)···H(6)	2.86 (3)	H(13)···N(2)^i	3.532 (17)
H(3)···H(7)	3.59 (3)	H(13)···C(1)^i	3.130 (16)
H(3)···H(8)	2.38 (3)	H(13)···C(2)^i	3.577 (16)
H(3)···H(9)	2.93 (3)	H(13)···C(5)^ix	3.511 (16)
H(3)···H(10)	2.37 (3)	H(13)···H(2)^i	3.04 (2)
H(3)···H(11)	2.44 (3)	H(13)···H(7)^ix	3.35 (3)
H(3)···H(12)	2.58 (2)	H(13)···H(8)^ix	2.80 (3)
H(4)···H(6)	2.41 (3)	H(13)···H(14)^v	3.50 (3)
H(4)···H(7)	2.47 (3)	H(13)···H(17)^xiv	3.41 (2)
H(4)···H(8)	2.92 (3)	H(13)···H(16)^i	3.09 (3)
H(4)···H(9)	2.46 (3)	H(13)···H(18)^i	3.40 (3)
H(4)···H(10)	2.93 (3)	H(13)···H(18)^xiv	3.15 (3)
H(5)···H(6)	2.90 (3)	H(14)···O(2)^v	2.644 (19)
H(5)···H(7)	2.43 (3)	H(14)···O(3)^v	3.00 (2)
H(5)···H(8)	2.43 (3)	H(14)···N(2)^i	3.54 (2)
H(5)···H(9)	3.57 (3)	H(14)···N(2)^v	3.550 (18)
H(6)···H(9)	3.18 (3)	H(14)···N(2)^xiv	3.474 (18)
H(6)···H(10)	2.29 (3)	H(14)···C(1)^v	3.236 (19)
H(8)···H(10)	3.19 (3)	H(14)···C(7)^v	3.40 (2)
H(9)···H(12)	3.47 (3)	H(14)···H(13)^iii	3.50 (3)
H(11)···H(12)	2.32 (3)	H(14)···H(17)^i	3.50 (3)
H(12)···H(13)	2.23 (3)	H(14)···H(17)^xiv	2.83 (3)
H(12)···H(14)	3.14 (3)	H(14)···H(16)^i	3.48 (3)
H(12)···H(15)	3.20 (3)	H(14)···H(16)^v	3.31 (3)
O(2)···H(14)^iii	2.644 (19)	H(14)···H(18)^i	3.11 (3)
O(2)···H(15)^iii	3.291 (18)	H(14)···H(18)^v	2.97 (3)
O(2)···H(17)^i	1.893 (16)	H(14)···H(18)^xiv	3.31 (3)
O(2)···H(17)^ii	3.262 (16)	H(15)···O(2)^v	3.291 (18)
O(2)···H(16)	2.766 (17)	H(15)···O(3)^i	3.552 (18)
O(2)···H(16)^i	3.146 (17)	H(15)···N(2)^xiv	3.558 (18)
O(2)···H(16)^ii	3.160 (17)	H(15)···C(5)^ix	3.547 (18)
O(2)···H(18)^i	3.375 (15)	H(15)···C(6)^viii	3.265 (19)
O(2)···H(18)^ii	3.262 (17)	H(15)···H(6)^ix	3.49 (3)
O(2)···H(19)^i	3.102 (16)	H(15)···H(7)^ix	3.49 (3)
O(2)···H(19)^ii	1.903 (18)	H(15)···H(8)^ix	3.03 (3)
O(1)···H(11)^iv	2.469 (17)	H(15)···H(9)^viii	2.96 (3)
O(1)···H(12)^iv	2.101 (16)	H(15)···H(10)^viii	3.28 (3)
O(1)···H(13)^iv	2.716 (16)	H(15)···H(11)^viii	2.96 (3)
O(1)···H(17)	3.102 (16)	H(15)···H(17)^xiv	3.11 (3)
O(1)···H(16)	1.909 (17)	H(15)···H(18)^v	3.14 (3)
O(1)···H(18)	3.265 (16)	H(15)···H(18)^xiv	3.32 (3)
O(1)···H(19)	3.278 (17)	H(17)···O(2)^iv	1.893 (16)
O(1)···H(19)^ii	3.203 (17)	H(17)···O(2)^vi	3.262 (16)
O(3)···H(7)^vii	3.142 (19)	H(17)···O(1)	3.102 (16)
O(3)···H(9)^viii	3.159 (17)	H(17)···O(3)^iii	3.240 (15)
O(3)···H(13)^iv	2.715 (17)	H(17)···N(1)^iv	2.948 (16)
O(3)···H(14)^iii	3.00 (2)	H(17)···N(2)^vi	3.430 (16)
O(3)···H(15)^iv	3.552 (18)	H(17)···C(1)^iv	2.962 (16)
O(3)···H(17)^v	3.240 (15)	H(17)···C(2)^iv	3.452 (16)
O(3)···H(16)^v	3.238 (15)	H(17)···C(7)^iv	3.221 (16)
O(3)···H(18)^v	1.867 (15)	H(17)···C(8)^x	3.298 (15)
O(3)···H(19)^v	3.260 (17)	H(17)···H(11)^iv	3.26 (3)
N(1)···H(8)^ix	3.11 (2)	H(17)···H(12)^iv	2.89 (3)
N(1)···H(17)^i	2.948 (16)	H(17)···H(13)^x	3.41 (2)
N(1)···H(16)^i	3.140 (17)	H(17)···H(14)^iv	3.50 (3)
N(2)···H(9)^vi	3.484 (17)	H(17)···H(14)^x	2.83 (3)
N(2)···H(11)^iv	3.505 (17)	H(17)···H(15)^x	3.11 (3)
N(2)···H(12)^iv	3.178 (15)	H(17)···H(16)^vi	3.29 (3)
N(2)···H(13)^iv	3.532 (17)	H(17)···H(19)^vi	2.78 (3)
N(2)···H(14)^iv	3.54 (2)	H(16)···O(2)^iv	3.146 (17)
N(2)···H(14)^x	3.474 (18)	H(16)···O(2)	2.766 (17)
N(2)···H(14)^iii	3.550 (18)	H(16)···O(2)^vi	3.160 (17)
N(2)···H(15)^x	3.558 (18)	H(16)···O(1)	1.909 (17)
N(2)···H(17)^ii	3.430 (16)	H(16)···O(3)^iii	3.238 (15)
N(2)···H(19)^vi	3.416 (16)	H(16)···N(1)^iv	3.140 (17)
N(2)···H(19)^ii	3.482 (16)	H(16)···C(1)	2.618 (17)
C(1)···H(11)^iv	3.598 (18)	H(16)···C(7)^iv	3.543 (17)
C(1)···H(12)^iv	3.226 (16)	H(16)···C(8)^iv	3.509 (16)
C(1)···H(13)^iv	3.130 (16)	H(16)···H(11)^iv	3.00 (3)
C(1)···H(14)^iii	3.236 (19)	H(16)···H(12)^iv	2.67 (3)
C(1)···H(17)^i	2.962 (16)	H(16)···H(13)^iv	3.09 (3)
C(1)···H(16)	2.618 (17)	H(16)···H(14)^iv	3.48 (3)
C(1)···H(19)^ii	2.783 (18)	H(16)···H(14)^iii	3.31 (3)
C(2)···H(5)^vii	3.575 (17)	H(16)···H(17)^ii	3.29 (3)
C(2)···H(7)^vii	3.53 (2)	H(16)···H(19)^ii	3.02 (3)
C(2)···H(13)^iv	3.577 (16)	H(18)···O(2)^iv	3.375 (15)
C(2)···H(17)^i	3.452 (16)	H(18)···O(2)^vi	3.262 (17)
C(3)···H(5)^vii	3.468 (18)	H(18)···O(1)	3.265 (16)
C(4)···H(2)^vii	3.393 (13)	H(18)···O(3)^iii	1.867 (15)
C(4)···H(5)^vii	3.055 (18)	H(18)···C(7)^iii	2.806 (15)
C(4)···H(6)^xi	3.312 (17)	H(18)···C(8)^iv	3.539 (17)
C(4)···H(7)^xi	3.48 (2)	H(18)···C(8)^x	3.453 (15)
C(5)···H(2)^vii	2.975 (14)	H(18)···C(8)^iii	3.206 (15)
C(5)···H(4)^xi	3.154 (16)	H(18)···H(9)^vi	3.09 (3)
C(5)···H(5)^vii	3.485 (18)	H(18)···H(13)^iv	3.40 (3)
C(5)···H(6)^xi	3.202 (18)	H(18)···H(13)^x	3.15 (3)
C(5)···H(7)^xi	3.40 (2)	H(18)···H(14)^iv	3.11 (3)
C(5)···H(10)^xii	3.350 (18)	H(18)···H(14)^x	3.31 (3)
C(5)···H(13)^ix	3.511 (16)	H(18)···H(14)^iii	2.97 (3)
C(5)···H(15)^ix	3.547 (18)	H(18)···H(15)^x	3.32 (3)
C(6)···H(4)^i	3.406 (16)	H(18)···H(15)^iii	3.14 (3)
C(6)···H(6)^xii	3.341 (17)	H(19)···O(2)^iv	3.102 (16)
C(6)···H(7)^xi	3.571 (19)	H(19)···O(2)^vi	1.903 (18)
C(6)···H(15)^xiii	3.265 (19)	H(19)···O(1)	3.278 (17)
C(7)···H(8)^ix	3.32 (2)	H(19)···O(1)^vi	3.203 (17)
C(7)···H(9)^viii	3.571 (17)	H(19)···O(3)^iii	3.260 (17)
C(7)···H(14)^iii	3.40 (2)	H(19)···N(2)^vi	3.482 (16)
C(7)···H(17)^i	3.221 (16)	H(19)···N(2)^ii	3.416 (16)
C(7)···H(16)^i	3.543 (17)	H(19)···C(1)^vi	2.783 (18)
C(7)···H(18)^v	2.806 (15)	H(19)···H(9)^vi	3.02 (3)
C(8)···H(8)^ix	3.150 (19)	H(19)···H(17)^ii	2.78 (3)
C(8)···H(17)^xiv	3.298 (15)	H(19)···H(16)^vi	3.02 (3)
C(8)···H(16)^i	3.509 (16)	H(19)···H(19)^vi	3.18 (3)
C(8)···H(18)^i	3.539 (17)	H(19)···H(19)^ii	3.18 (3)
C(8)···H(18)^v	3.206 (15)
C(2)—N(1)—C(7)	119.87 (9)	C(4)—C(3)—H(3)	105.4 (8)
O(2)—C(1)—O(1)	124.28 (10)	C(6)—C(3)—H(3)	106.5 (9)
O(2)—C(1)—C(2)	119.09 (9)	C(3)—C(4)—H(4)	108.9 (9)
O(1)—C(1)—C(2)	116.61 (9)	C(3)—C(4)—H(5)	109.4 (10)
N(1)—C(2)—C(1)	112.10 (9)	C(5)—C(4)—H(4)	109.8 (9)
N(1)—C(2)—C(3)	110.52 (9)	C(5)—C(4)—H(5)	109.7 (10)
C(1)—C(2)—C(3)	111.92 (9)	H(4)—C(4)—H(5)	106.0 (13)
C(2)—C(3)—C(4)	110.92 (9)	C(4)—C(5)—H(6)	110.3 (9)
C(2)—C(3)—C(6)	112.93 (10)	C(4)—C(5)—H(7)	111.8 (10)
C(4)—C(3)—C(6)	111.31 (10)	C(4)—C(5)—H(8)	110.1 (11)
C(3)—C(4)—C(5)	112.78 (12)	H(6)—C(5)—H(7)	108.7 (14)
O(3)—C(7)—N(1)	121.07 (10)	H(6)—C(5)—H(8)	107.3 (15)
O(3)—C(7)—C(8)	121.92 (10)	H(7)—C(5)—H(8)	108.5 (15)
N(1)—C(7)—C(8)	117.01 (9)	C(3)—C(6)—H(9)	109.9 (10)
C(2)—N(1)—H(12)	122.1 (10)	C(3)—C(6)—H(10)	110.8 (11)
C(7)—N(1)—H(12)	117.7 (10)	C(3)—C(6)—H(11)	111.1 (11)
H(17)—N(2)—H(16)	108.9 (14)	H(9)—C(6)—H(10)	106.3 (14)
H(17)—N(2)—H(18)	111.2 (13)	H(9)—C(6)—H(11)	110.3 (14)
H(17)—N(2)—H(19)	106.9 (14)	H(10)—C(6)—H(11)	108.2 (14)
H(16)—N(2)—H(18)	110.1 (14)	C(7)—C(8)—H(13)	112.2 (10)
H(16)—N(2)—H(19)	109.3 (14)	C(7)—C(8)—H(14)	108.5 (11)
H(18)—N(2)—H(19)	110.4 (14)	C(7)—C(8)—H(15)	108.3 (11)
N(1)—C(2)—H(2)	107.1 (8)	H(13)—C(8)—H(14)	110.4 (15)
C(1)—C(2)—H(2)	106.4 (8)	H(13)—C(8)—H(15)	112.1 (15)
C(3)—C(2)—H(2)	108.6 (7)	H(14)—C(8)—H(15)	105.0 (16)
C(2)—C(3)—H(3)	109.4 (8)
C(2)—N(1)—C(7)—O(3)	0.46 (15)	O(1)—C(1)—C(2)—C(3)	83.09 (10)
C(2)—N(1)—C(7)—C(8)	−179.92 (8)	N(1)—C(2)—C(3)—C(4)	164.20 (8)
C(7)—N(1)—C(2)—C(1)	69.53 (12)	N(1)—C(2)—C(3)—C(6)	−70.05 (11)
C(7)—N(1)—C(2)—C(3)	−164.87 (9)	C(1)—C(2)—C(3)—C(4)	−70.09 (11)
O(2)—C(1)—C(2)—N(1)	29.85 (12)	C(1)—C(2)—C(3)—C(6)	55.66 (11)
O(2)—C(1)—C(2)—C(3)	−94.99 (10)	C(2)—C(3)—C(4)—C(5)	−161.12 (9)
O(1)—C(1)—C(2)—N(1)	−152.07 (8)	C(6)—C(3)—C(4)—C(5)	72.23 (12)

Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+5/2, y−1/2, −z+1/2; (iv) x, y−1, z; (v) −x+5/2, y+1/2, −z+1/2; (vi) −x+3/2, y−1/2, −z+1/2; (vii) −x+2, −y, −z; (viii) x+1, y, z; (ix) −x+2, −y+1, −z; (x) −x+5/2, y−3/2, −z+1/2; (xi) −x+1, −y, −z; (xii) −x+1, −y+1, −z; (xiii) x−1, y, z; (xiv) −x+5/2, y+3/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N(1)—H(12)···O(1)^i	0.878 (17)	2.101 (16)	2.9399 (15)	159.7 (14)
N(2)—H(17)···O(2)^iv	0.918 (17)	1.893 (16)	2.7956 (16)	166.2 (13)
N(2)—H(16)···O(1)	0.895 (17)	1.909 (17)	2.7895 (15)	168.3 (16)
N(2)—H(18)···O(3)^iii	0.949 (16)	1.867 (15)	2.8130 (15)	177.5 (14)
N(2)—H(19)···O(2)^vi	0.91 (2)	1.903 (18)	2.8112 (16)	172.2 (15)

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

(Ac-DL-aIleNH3)

Crystal data

C8H18N2O3	Dx = 1.182 Mg m^−3
Mr = 190.24	Melting point = 171–173 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6092 reflections
a = 24.376 (3) Å	θ = 3.2–27.5°
b = 7.5507 (8) Å	µ = 0.09 mm^−1
c = 5.8064 (5) Å	T = 296 K
V = 1068.70 (18) Å^3	Needle, colorless
Z = 4	0.45 × 0.02 × 0.02 mm
F(000) = 416.00

Data collection

Rigaku R-AXIS RAPID diffractometer	1340 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.107
ω scans	θmax = 27.5°
Absorption correction: multi-scan ABSCOR (Rigaku, 1995)	h = −31→30
Tmin = 0.441, Tmax = 0.998	k = −9→9
10031 measured reflections	l = −7→6
2299 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	Only H-atom coordinates refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.069P)^2] where P = (Fo^2 + 2Fc^2)/3
2299 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.21 e Å^−3
1 restraint	Δρmin = −0.38 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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

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

	x	y	z	Uiso*/Ueq
O(1)	0.39641 (10)	0.3190 (4)	0.4103 (4)	0.0388 (7)
O(2)	0.45083 (10)	0.3368 (4)	0.7185 (4)	0.0349 (6)
O(3)	0.42518 (10)	−0.0952 (4)	0.7799 (4)	0.0390 (7)
N(1)	0.38192 (10)	0.1229 (4)	0.9732 (5)	0.0302 (7)
N(2)	0.49437 (14)	0.3419 (5)	1.1629 (7)	0.0351 (8)
C(1)	0.40615 (14)	0.2907 (5)	0.6194 (6)	0.0330 (8)
C(2)	0.36161 (14)	0.1991 (5)	0.7585 (6)	0.0311 (8)
C(3)	0.31260 (15)	0.3224 (5)	0.7977 (7)	0.0392 (9)
C(4)	0.26513 (17)	0.2241 (7)	0.9170 (9)	0.0513 (11)
C(5)	0.21054 (18)	0.3180 (8)	0.8962 (10)	0.0611 (13)
C(6)	0.32904 (18)	0.4925 (6)	0.9222 (8)	0.0482 (11)
C(7)	0.41341 (12)	−0.0236 (5)	0.9677 (6)	0.0324 (8)
C(8)	0.43278 (18)	−0.0977 (6)	1.1936 (7)	0.0412 (10)
H(2)	0.3477 (13)	0.091 (6)	0.678 (8)	0.042 (11)*
H(3)	0.2998 (16)	0.357 (5)	0.637 (7)	0.042 (10)*
H(4)	0.2630 (16)	0.091 (7)	0.846 (8)	0.057 (13)*
H(5)	0.2767 (19)	0.232 (6)	1.077 (9)	0.063 (15)*
H(6)	0.2018 (17)	0.343 (6)	0.720 (10)	0.063 (14)*
H(7)	0.179 (2)	0.246 (6)	0.972 (11)	0.079 (15)*
H(8)	0.214 (3)	0.451 (9)	0.983 (13)	0.13 (3)*
H(9)	0.2970 (15)	0.583 (5)	0.941 (7)	0.050 (11)*
H(10)	0.3394 (16)	0.466 (7)	1.083 (8)	0.051 (12)*
H(11)	0.3581 (18)	0.564 (7)	0.825 (8)	0.060 (13)*
H(12)	0.3768 (17)	0.196 (6)	1.120 (8)	0.055 (13)*
H(13)	0.4173 (16)	−0.224 (7)	1.198 (8)	0.049 (11)*
H(14)	0.4206 (18)	−0.025 (7)	1.309 (8)	0.069 (15)*
H(15)	0.476 (3)	−0.105 (7)	1.185 (10)	0.083 (15)*
H(16)	0.4788 (17)	0.321 (6)	1.038 (9)	0.048 (14)*
H(17)	0.462 (3)	0.339 (8)	1.280 (9)	0.082 (17)*
H(18)	0.5109 (16)	0.445 (6)	1.169 (7)	0.036 (11)*
H(19)	0.5239 (17)	0.249 (7)	1.212 (8)	0.054 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.0427 (14)	0.0446 (16)	0.0289 (14)	−0.0006 (12)	−0.0031 (12)	0.0005 (12)
O(2)	0.0357 (12)	0.0327 (14)	0.0361 (15)	−0.0054 (11)	−0.0005 (11)	−0.0013 (11)
O(3)	0.0438 (13)	0.0356 (16)	0.0376 (14)	0.0056 (12)	−0.0001 (12)	−0.0040 (12)
N(1)	0.0323 (14)	0.0290 (15)	0.0293 (16)	0.0012 (11)	0.0023 (14)	0.0013 (13)
N(2)	0.0383 (18)	0.0338 (19)	0.0333 (18)	−0.0060 (15)	−0.0043 (16)	−0.0000 (15)
C(1)	0.0350 (19)	0.030 (2)	0.034 (2)	−0.0001 (15)	0.0034 (16)	−0.0018 (16)
C(2)	0.0342 (17)	0.031 (2)	0.0286 (18)	−0.0001 (15)	−0.0028 (16)	0.0020 (16)
C(3)	0.0381 (19)	0.041 (3)	0.038 (3)	0.0066 (17)	−0.0018 (18)	0.0040 (19)
C(4)	0.038 (2)	0.070 (4)	0.045 (3)	0.0050 (19)	0.006 (2)	0.005 (3)
C(5)	0.041 (3)	0.081 (4)	0.061 (3)	0.010 (3)	0.004 (3)	−0.008 (3)
C(6)	0.055 (3)	0.044 (3)	0.045 (3)	0.013 (2)	−0.004 (3)	−0.007 (2)
C(7)	0.0348 (17)	0.0315 (18)	0.0310 (19)	−0.0040 (14)	0.0011 (16)	0.0006 (17)
C(8)	0.051 (3)	0.038 (3)	0.035 (2)	0.0080 (19)	−0.0043 (19)	0.0013 (19)

Geometric parameters (Å, º)

O(1)—C(1)	1.256 (5)	N(2)—H(19)	1.05 (5)
O(2)—C(1)	1.280 (5)	C(2)—H(2)	1.00 (4)
O(3)—C(7)	1.250 (5)	C(3)—H(3)	1.02 (4)
N(1)—C(2)	1.460 (5)	C(4)—H(4)	1.09 (5)
N(1)—C(7)	1.347 (5)	C(4)—H(5)	0.97 (5)
C(1)—C(2)	1.519 (5)	C(5)—H(6)	1.06 (6)
C(2)—C(3)	1.532 (6)	C(5)—H(7)	1.04 (5)
C(3)—C(4)	1.540 (6)	C(5)—H(8)	1.13 (7)
C(3)—C(6)	1.527 (6)	C(6)—H(9)	1.04 (4)
C(4)—C(5)	1.513 (7)	C(6)—H(10)	0.99 (5)
C(7)—C(8)	1.502 (6)	C(6)—H(11)	1.06 (5)
N(1)—H(12)	1.02 (5)	C(8)—H(13)	1.03 (5)
N(2)—H(16)	0.84 (5)	C(8)—H(14)	0.92 (5)
N(2)—H(17)	1.05 (6)	C(8)—H(15)	1.05 (6)
N(2)—H(18)	0.88 (4)
O(1)···C(3)	3.039 (5)	H(3)···H(5)^i	3.43 (7)
O(2)···O(3)	3.340 (4)	H(3)···H(5)^xi	3.41 (6)
O(2)···N(1)	2.760 (4)	H(3)···H(7)^xi	3.13 (6)
O(2)···C(3)	3.403 (5)	H(3)···H(8)^vii	3.21 (8)
O(2)···C(6)	3.405 (5)	H(3)···H(9)^vii	3.34 (6)
O(2)···C(7)	3.214 (4)	H(3)···H(10)^i	3.46 (6)
O(3)···C(1)	3.094 (5)	H(4)···C(5)^vii	3.39 (5)
O(3)···C(2)	2.712 (5)	H(4)···C(6)^vii	3.41 (5)
N(1)···C(4)	2.966 (5)	H(4)···H(3)^ix	2.88 (6)
N(1)···C(6)	3.088 (6)	H(4)···H(5)^vii	3.27 (7)
C(1)···C(6)	2.991 (6)	H(4)···H(6)^ix	2.99 (7)
C(1)···C(7)	3.123 (5)	H(4)···H(8)^vii	2.42 (9)
C(5)···C(6)	3.179 (7)	H(4)···H(9)^vii	2.77 (6)
O(1)···N(1)^i	2.959 (4)	H(4)···H(10)^vii	3.07 (6)
O(1)···N(2)^i	2.792 (5)	H(5)···O(1)^iv	3.56 (5)
O(1)···C(6)^i	3.528 (6)	H(5)···H(3)^iv	3.43 (7)
O(1)···C(8)^i	3.503 (6)	H(5)···H(3)^ix	3.41 (6)
O(2)···N(2)^i	3.396 (5)	H(5)···H(4)^x	3.27 (7)
O(2)···N(2)	2.790 (5)	H(5)···H(6)^ix	3.10 (7)
O(2)···N(2)^ii	2.789 (5)	H(5)···H(8)^ix	3.18 (9)
O(2)···C(8)^iii	3.366 (5)	H(5)···H(9)^ix	2.99 (7)
O(3)···N(2)^iii	2.789 (5)	H(6)···N(1)^xi	3.27 (5)
O(3)···C(8)^i	3.409 (5)	H(6)···C(4)^xi	3.47 (5)
N(1)···O(1)^iv	2.959 (4)	H(6)···C(6)^vii	3.25 (5)
N(1)···N(2)	3.385 (5)	H(6)···C(7)^xi	3.33 (5)
N(2)···O(1)^iv	2.792 (5)	H(6)···C(8)^xi	3.32 (5)
N(2)···O(2)	2.790 (5)	H(6)···H(2)^x	3.47 (7)
N(2)···O(2)^iv	3.396 (5)	H(6)···H(4)^xi	2.99 (7)
N(2)···O(2)^v	2.789 (5)	H(6)···H(5)^xi	3.10 (7)
N(2)···O(3)^vi	2.789 (5)	H(6)···H(9)^vii	2.55 (7)
N(2)···N(1)	3.385 (5)	H(6)···H(10)^vii	3.12 (7)
N(2)···C(1)^iv	3.435 (5)	H(6)···H(11)^vii	3.44 (7)
N(2)···C(7)	3.577 (5)	H(6)···H(12)^xi	3.33 (6)
C(1)···N(2)^i	3.435 (5)	H(6)···H(13)^xi	2.95 (6)
C(6)···O(1)^iv	3.528 (6)	H(6)···H(14)^xi	3.19 (6)
C(7)···N(2)	3.577 (5)	H(7)···O(3)^x	3.33 (6)
C(8)···O(1)^iv	3.503 (6)	H(7)···C(6)^ix	3.25 (6)
C(8)···O(2)^vi	3.366 (5)	H(7)···C(8)^xi	3.38 (6)
C(8)···O(3)^iv	3.409 (5)	H(7)···H(2)^x	2.94 (7)
O(1)···H(2)	2.61 (4)	H(7)···H(3)^ix	3.13 (6)
O(1)···H(3)	2.71 (4)	H(7)···H(9)^vii	3.37 (7)
O(1)···H(11)	3.18 (5)	H(7)···H(9)^ix	3.04 (7)
O(2)···H(2)	3.13 (4)	H(7)···H(10)^vii	3.12 (8)
O(2)···H(10)	3.58 (5)	H(7)···H(11)^ix	2.63 (8)
O(2)···H(11)	2.90 (5)	H(7)···H(13)^xi	2.84 (7)
O(2)···H(12)	3.13 (5)	H(7)···H(14)^xi	3.12 (7)
O(3)···H(2)	2.43 (4)	H(8)···C(2)^x	3.07 (7)
O(3)···H(12)	3.18 (5)	H(8)···C(3)^x	3.41 (7)
O(3)···H(13)	2.62 (5)	H(8)···C(4)^x	3.29 (7)
O(3)···H(14)	3.12 (5)	H(8)···H(2)^x	2.16 (8)
O(3)···H(15)	2.66 (6)	H(8)···H(3)^x	3.21 (8)
N(1)···H(3)	3.31 (4)	H(8)···H(4)^x	2.42 (9)
N(1)···H(4)	3.00 (4)	H(8)···H(5)^xi	3.18 (9)
N(1)···H(5)	2.76 (5)	H(8)···H(12)^xi	3.57 (8)
N(1)···H(10)	2.86 (5)	H(8)···H(14)^xi	3.43 (7)
N(1)···H(11)	3.49 (5)	H(9)···C(4)^xi	3.56 (4)
N(1)···H(13)	3.05 (5)	H(9)···C(4)^x	3.33 (4)
N(1)···H(14)	2.44 (5)	H(9)···C(5)^x	3.19 (4)
N(1)···H(15)	3.12 (6)	H(9)···H(3)^x	3.34 (6)
C(1)···H(3)	2.64 (4)	H(9)···H(4)^x	2.77 (6)
C(1)···H(10)	3.41 (5)	H(9)···H(5)^xi	2.99 (7)
C(1)···H(11)	2.66 (5)	H(9)···H(6)^x	2.55 (7)
C(1)···H(12)	3.08 (5)	H(9)···H(7)^xi	3.04 (7)
C(2)···H(4)	2.59 (4)	H(9)···H(7)^x	3.37 (7)
C(2)···H(5)	2.79 (5)	H(9)···H(13)^xii	3.60 (6)
C(2)···H(9)	3.46 (4)	H(10)···O(1)^iv	2.60 (5)
C(2)···H(10)	2.81 (5)	H(10)···C(5)^x	3.44 (5)
C(2)···H(11)	2.78 (5)	H(10)···H(3)^iv	3.46 (6)
C(3)···H(6)	2.74 (5)	H(10)···H(4)^x	3.07 (6)
C(3)···H(7)	3.46 (5)	H(10)···H(6)^x	3.12 (7)
C(3)···H(8)	2.81 (6)	H(10)···H(7)^x	3.12 (8)
C(3)···H(12)	2.62 (5)	H(10)···H(13)^xii	3.09 (7)
C(4)···H(2)	2.64 (4)	H(10)···H(16)	3.58 (6)
C(4)···H(9)	2.82 (4)	H(10)···H(17)	3.33 (7)
C(4)···H(10)	2.75 (5)	H(11)···O(3)^xii	3.06 (5)
C(4)···H(11)	3.47 (5)	H(11)···C(5)^xi	3.56 (5)
C(4)···H(12)	2.97 (5)	H(11)···C(7)^xii	3.49 (5)
C(5)···H(3)	2.66 (4)	H(11)···H(6)^x	3.44 (7)
C(5)···H(9)	2.92 (4)	H(11)···H(7)^xi	2.63 (8)
C(5)···H(10)	3.51 (4)	H(11)···H(13)^xii	3.06 (7)
C(6)···H(2)	3.38 (4)	H(11)···H(18)^ii	3.32 (6)
C(6)···H(4)	3.46 (5)	H(11)···H(19)^ii	3.27 (7)
C(6)···H(5)	2.51 (5)	H(12)···O(1)^iv	1.98 (5)
C(6)···H(6)	3.50 (5)	H(12)···N(2)	3.08 (5)
C(6)···H(8)	2.85 (6)	H(12)···C(1)^iv	3.07 (5)
C(6)···H(12)	2.77 (5)	H(12)···H(2)^iv	3.41 (6)
C(7)···H(2)	2.48 (4)	H(12)···H(6)^ix	3.33 (6)
C(8)···H(12)	2.64 (5)	H(12)···H(8)^ix	3.57 (8)
H(2)···H(3)	2.33 (6)	H(12)···H(16)	2.70 (6)
H(2)···H(4)	2.28 (5)	H(12)···H(17)	2.51 (7)
H(2)···H(5)	3.08 (7)	H(13)···O(2)^vi	3.33 (4)
H(2)···H(12)	2.78 (6)	H(13)···O(3)^iv	3.52 (5)
H(3)···H(4)	2.51 (6)	H(13)···N(2)^vi	3.57 (5)
H(3)···H(5)	2.78 (7)	H(13)···C(5)^ix	3.34 (4)
H(3)···H(6)	2.44 (6)	H(13)···C(6)^viii	3.43 (5)
H(3)···H(8)	2.99 (8)	H(13)···H(6)^ix	2.95 (6)
H(3)···H(9)	2.45 (6)	H(13)···H(7)^ix	2.84 (7)
H(3)···H(10)	2.89 (6)	H(13)···H(9)^viii	3.60 (6)
H(3)···H(11)	2.38 (6)	H(13)···H(10)^viii	3.09 (7)
H(3)···H(12)	3.59 (6)	H(13)···H(11)^viii	3.06 (7)
H(4)···H(6)	2.53 (7)	H(13)···H(16)^vi	3.29 (6)
H(4)···H(7)	2.47 (7)	H(13)···H(17)^viii	3.51 (7)
H(4)···H(8)	3.08 (8)	H(13)···H(18)^viii	3.39 (6)
H(4)···H(12)	3.29 (6)	H(13)···H(19)^iii	3.17 (7)
H(5)···H(6)	2.89 (7)	H(13)···H(19)^vi	3.31 (7)
H(5)···H(7)	2.46 (7)	H(14)···O(1)^iv	2.73 (5)
H(5)···H(8)	2.32 (8)	H(14)···O(3)^iv	2.78 (5)
H(5)···H(9)	2.81 (6)	H(14)···N(2)	3.41 (5)
H(5)···H(10)	2.34 (7)	H(14)···C(1)^iv	3.01 (5)
H(5)···H(11)	3.52 (7)	H(14)···C(2)^iv	3.43 (5)
H(5)···H(12)	2.47 (7)	H(14)···C(5)^ix	3.45 (5)
H(6)···H(9)	3.21 (6)	H(14)···H(2)^iv	2.92 (6)
H(8)···H(9)	2.27 (7)	H(14)···H(6)^ix	3.19 (6)
H(8)···H(10)	3.12 (7)	H(14)···H(7)^ix	3.12 (7)
H(10)···H(12)	2.25 (7)	H(14)···H(8)^ix	3.43 (7)
H(11)···H(12)	3.30 (7)	H(14)···H(15)^vi	3.48 (7)
H(12)···H(13)	3.35 (7)	H(14)···H(16)	3.37 (7)
H(12)···H(14)	2.27 (7)	H(14)···H(16)^vi	3.57 (7)
H(12)···H(15)	3.34 (7)	H(14)···H(17)	2.93 (8)
O(1)···H(5)^i	3.56 (5)	H(14)···H(19)	3.31 (7)
O(1)···H(10)^i	2.60 (5)	H(14)···H(19)^vi	3.18 (7)
O(1)···H(12)^i	1.98 (5)	H(15)···O(2)^vi	2.51 (6)
O(1)···H(14)^i	2.73 (5)	H(15)···O(3)^vi	2.90 (6)
O(1)···H(16)^i	2.95 (5)	H(15)···N(2)	3.41 (5)
O(1)···H(17)^i	1.77 (6)	H(15)···N(2)^iii	3.59 (6)
O(1)···H(18)^i	3.26 (4)	H(15)···N(2)^vi	3.38 (6)
O(1)···H(18)^ii	3.25 (4)	H(15)···C(1)^vi	3.22 (6)
O(1)···H(19)^i	3.36 (4)	H(15)···C(7)^vi	3.31 (6)
O(2)···H(13)^iii	3.33 (4)	H(15)···H(14)^iii	3.48 (7)
O(2)···H(15)^iii	2.51 (6)	H(15)···H(15)^iii	3.51 (8)
O(2)···H(16)	1.98 (5)	H(15)···H(15)^vi	3.51 (8)
O(2)···H(16)^ii	3.27 (4)	H(15)···H(16)	3.33 (7)
O(2)···H(17)^i	2.56 (6)	H(15)···H(16)^vi	2.84 (7)
O(2)···H(17)	3.27 (6)	H(15)···H(17)	3.41 (8)
O(2)···H(17)^ii	3.27 (6)	H(15)···H(17)^iii	3.31 (8)
O(2)···H(18)	3.11 (4)	H(15)···H(18)^viii	3.50 (7)
O(2)···H(18)^ii	1.91 (4)	H(15)···H(19)	2.92 (7)
O(2)···H(19)^i	3.50 (5)	H(15)···H(19)^iii	2.96 (7)
O(2)···H(19)	3.44 (5)	H(15)···H(19)^vi	3.24 (7)
O(2)···H(19)^ii	3.19 (5)	H(16)···O(1)^iv	2.95 (5)
O(3)···H(7)^vii	3.33 (6)	H(16)···O(2)	1.98 (5)
O(3)···H(11)^viii	3.06 (5)	H(16)···O(2)^v	3.27 (4)
O(3)···H(13)^i	3.52 (5)	H(16)···O(3)^vi	3.22 (5)
O(3)···H(14)^i	2.78 (5)	H(16)···N(1)	2.82 (4)
O(3)···H(15)^iii	2.90 (6)	H(16)···N(2)^ii	3.41 (5)
O(3)···H(16)^iii	3.22 (5)	H(16)···C(1)	3.01 (5)
O(3)···H(17)^iii	3.32 (6)	H(16)···C(2)	3.41 (5)
O(3)···H(18)^iii	3.13 (4)	H(16)···C(7)	3.08 (4)
O(3)···H(19)^iii	1.74 (5)	H(16)···C(8)	3.48 (4)
N(1)···H(6)^ix	3.27 (5)	H(16)···C(8)^iii	3.39 (5)
N(1)···H(16)	2.82 (4)	H(16)···H(10)	3.58 (6)
N(1)···H(17)	3.10 (6)	H(16)···H(12)	2.70 (6)
N(2)···H(12)	3.08 (5)	H(16)···H(13)^iii	3.29 (6)
N(2)···H(13)^iii	3.57 (5)	H(16)···H(14)	3.37 (7)
N(2)···H(14)	3.41 (5)	H(16)···H(14)^iii	3.57 (7)
N(2)···H(15)	3.41 (5)	H(16)···H(15)	3.33 (7)
N(2)···H(15)^iii	3.38 (6)	H(16)···H(15)^iii	2.84 (7)
N(2)···H(15)^vi	3.59 (6)	H(16)···H(17)^ii	3.31 (7)
N(2)···H(16)^v	3.41 (5)	H(16)···H(18)^ii	2.78 (6)
N(2)···H(17)^ii	3.45 (6)	H(17)···O(1)^iv	1.77 (6)
N(2)···H(18)^ii	3.29 (4)	H(17)···O(2)	3.27 (6)
N(2)···H(18)^v	3.35 (4)	H(17)···O(2)^iv	2.56 (6)
C(1)···H(12)^i	3.07 (5)	H(17)···O(2)^v	3.27 (6)
C(1)···H(14)^i	3.01 (5)	H(17)···O(3)^vi	3.32 (6)
C(1)···H(15)^iii	3.22 (6)	H(17)···N(1)	3.10 (6)
C(1)···H(16)	3.01 (5)	H(17)···N(2)^v	3.45 (6)
C(1)···H(17)^i	2.42 (6)	H(17)···C(1)^iv	2.42 (6)
C(1)···H(18)^ii	2.85 (4)	H(17)···C(7)	3.49 (6)
C(2)···H(8)^vii	3.07 (7)	H(17)···C(8)	3.41 (6)
C(2)···H(14)^i	3.43 (5)	H(17)···H(10)	3.33 (7)
C(2)···H(16)	3.41 (5)	H(17)···H(12)	2.51 (7)
C(3)···H(8)^vii	3.41 (7)	H(17)···H(13)^xii	3.51 (7)
C(4)···H(3)^ix	3.44 (4)	H(17)···H(14)	2.93 (8)
C(4)···H(6)^ix	3.47 (5)	H(17)···H(15)	3.41 (8)
C(4)···H(8)^vii	3.29 (7)	H(17)···H(15)^vi	3.31 (8)
C(4)···H(9)^vii	3.33 (4)	H(17)···H(16)^v	3.31 (7)
C(4)···H(9)^ix	3.56 (4)	H(17)···H(18)^v	2.87 (7)
C(5)···H(2)^x	2.99 (4)	H(18)···O(1)^iv	3.26 (4)
C(5)···H(4)^x	3.39 (5)	H(18)···O(1)^v	3.25 (4)
C(5)···H(9)^vii	3.19 (4)	H(18)···O(2)	3.11 (4)
C(5)···H(10)^vii	3.44 (5)	H(18)···O(2)^v	1.91 (4)
C(5)···H(11)^ix	3.56 (5)	H(18)···O(3)^vi	3.13 (4)
C(5)···H(13)^xi	3.34 (4)	H(18)···N(2)^ii	3.35 (4)
C(5)···H(14)^xi	3.45 (5)	H(18)···N(2)^v	3.29 (4)
C(6)···H(4)^x	3.41 (5)	H(18)···C(1)^v	2.85 (4)
C(6)···H(6)^x	3.25 (5)	H(18)···H(11)^v	3.32 (6)
C(6)···H(7)^xi	3.25 (6)	H(18)···H(13)^xii	3.39 (6)
C(6)···H(13)^xii	3.43 (5)	H(18)···H(15)^xii	3.50 (7)
C(7)···H(6)^ix	3.33 (5)	H(18)···H(16)^v	2.78 (6)
C(7)···H(11)^viii	3.49 (5)	H(18)···H(17)^ii	2.87 (7)
C(7)···H(15)^iii	3.31 (6)	H(18)···H(18)^ii	3.07 (6)
C(7)···H(16)	3.08 (4)	H(18)···H(18)^v	3.07 (6)
C(7)···H(17)	3.49 (6)	H(19)···O(1)^iv	3.36 (4)
C(7)···H(19)^iii	2.73 (5)	H(19)···O(2)	3.44 (5)
C(8)···H(6)^ix	3.32 (5)	H(19)···O(2)^iv	3.50 (5)
C(8)···H(7)^ix	3.38 (6)	H(19)···O(2)^v	3.19 (5)
C(8)···H(16)	3.48 (4)	H(19)···O(3)^vi	1.74 (5)
C(8)···H(16)^vi	3.39 (5)	H(19)···C(7)^vi	2.73 (5)
C(8)···H(17)	3.41 (6)	H(19)···C(8)	3.43 (5)
C(8)···H(19)	3.43 (5)	H(19)···C(8)^iii	3.39 (5)
C(8)···H(19)^iii	3.20 (5)	H(19)···C(8)^vi	3.20 (5)
C(8)···H(19)^vi	3.39 (5)	H(19)···H(11)^v	3.27 (7)
H(2)···C(5)^vii	2.99 (4)	H(19)···H(13)^iii	3.31 (7)
H(2)···H(6)^vii	3.47 (7)	H(19)···H(13)^vi	3.17 (7)
H(2)···H(7)^vii	2.94 (7)	H(19)···H(14)	3.31 (7)
H(2)···H(8)^vii	2.16 (8)	H(19)···H(14)^iii	3.18 (7)
H(2)···H(12)^i	3.41 (6)	H(19)···H(15)	2.92 (7)
H(2)···H(14)^i	2.92 (6)	H(19)···H(15)^iii	3.24 (7)
H(3)···C(4)^xi	3.44 (4)	H(19)···H(15)^vi	2.96 (7)
H(3)···H(4)^xi	2.88 (6)
C(2)—N(1)—C(7)	119.8 (3)	C(4)—C(3)—H(3)	108 (2)
O(1)—C(1)—O(2)	123.3 (4)	C(6)—C(3)—H(3)	107 (2)
O(1)—C(1)—C(2)	117.1 (3)	C(3)—C(4)—H(4)	108 (3)
O(2)—C(1)—C(2)	119.5 (3)	C(3)—C(4)—H(5)	101 (3)
N(1)—C(2)—C(1)	113.0 (3)	C(5)—C(4)—H(4)	111 (2)
N(1)—C(2)—C(3)	112.2 (3)	C(5)—C(4)—H(5)	108 (3)
C(1)—C(2)—C(3)	111.1 (3)	H(4)—C(4)—H(5)	115 (4)
C(2)—C(3)—C(4)	111.1 (4)	C(4)—C(5)—H(6)	110 (3)
C(2)—C(3)—C(6)	112.1 (4)	C(4)—C(5)—H(7)	112 (3)
C(4)—C(3)—C(6)	113.0 (4)	C(4)—C(5)—H(8)	109 (3)
C(3)—C(4)—C(5)	113.5 (5)	H(6)—C(5)—H(7)	110 (4)
O(3)—C(7)—N(1)	120.4 (3)	H(6)—C(5)—H(8)	107 (5)
O(3)—C(7)—C(8)	121.9 (4)	H(7)—C(5)—H(8)	109 (5)
N(1)—C(7)—C(8)	117.6 (4)	C(3)—C(6)—H(9)	114 (3)
C(2)—N(1)—H(12)	117 (3)	C(3)—C(6)—H(10)	110 (3)
C(7)—N(1)—H(12)	122 (3)	C(3)—C(6)—H(11)	111 (3)
H(16)—N(2)—H(17)	102 (4)	H(9)—C(6)—H(10)	103 (4)
H(16)—N(2)—H(18)	114 (4)	H(9)—C(6)—H(11)	103 (4)
H(16)—N(2)—H(19)	115 (4)	H(10)—C(6)—H(11)	116 (4)
H(17)—N(2)—H(18)	110 (4)	C(7)—C(8)—H(13)	105 (3)
H(17)—N(2)—H(19)	110 (4)	C(7)—C(8)—H(14)	108 (3)
H(18)—N(2)—H(19)	106 (4)	C(7)—C(8)—H(15)	107 (3)
N(1)—C(2)—H(2)	101 (3)	H(13)—C(8)—H(14)	115 (4)
C(1)—C(2)—H(2)	111 (3)	H(13)—C(8)—H(15)	109 (4)
C(3)—C(2)—H(2)	107.5 (19)	H(14)—C(8)—H(15)	113 (4)
C(2)—C(3)—H(3)	105 (2)
C(2)—N(1)—C(7)—O(3)	−0.3 (5)	O(2)—C(1)—C(2)—C(3)	108.2 (4)
C(2)—N(1)—C(7)—C(8)	−179.4 (3)	N(1)—C(2)—C(3)—C(4)	−58.2 (4)
C(7)—N(1)—C(2)—C(1)	−72.5 (4)	N(1)—C(2)—C(3)—C(6)	69.3 (4)
C(7)—N(1)—C(2)—C(3)	161.0 (3)	C(1)—C(2)—C(3)—C(4)	174.2 (3)
O(1)—C(1)—C(2)—N(1)	162.0 (3)	C(1)—C(2)—C(3)—C(6)	−58.3 (4)
O(1)—C(1)—C(2)—C(3)	−70.9 (4)	C(2)—C(3)—C(4)—C(5)	−162.4 (3)
O(2)—C(1)—C(2)—N(1)	−18.8 (5)	C(6)—C(3)—C(4)—C(5)	70.5 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N(1)—H(12)···O(1)^iv	1.02 (5)	1.98 (5)	2.959 (4)	159 (4)
N(2)—H(16)···O(2)	0.83 (5)	1.98 (5)	2.790 (5)	164 (4)
N(2)—H(17)···O(1)^iv	1.04 (6)	1.77 (6)	2.792 (5)	165 (5)
N(2)—H(18)···O(2)^v	0.88 (4)	1.91 (4)	2.789 (5)	174 (4)
N(2)—H(19)···O(3)^vi	1.05 (5)	1.74 (5)	2.789 (5)	177 (4)

Symmetry codes: (iv) x, y, z+1; (v) −x+1, −y+1, z+1/2; (vi) −x+1, −y, z+1/2.