Structure-forming units of amino acid maleates. Case study of L-valinium hydrogen maleate

A new salt of L-valinium hydrogen maleate was used as an example to study structure-forming units in amino acid maleates. This compound was crystallized, its structure solved from single-crystal X-ray diffraction data, and the phase purity of the bulk powder sample confirmed by X-ray powder diffraction and FT-IR spectra. The stability of the new salt was analyzed using density functional theory and PIXEL calculations with focus on the C²₂(12) structure-forming crystallographic motif. This motif was of particular interest as it is common for almost all maleates. The exceptionally high ability of maleic acid to form salts with various amino acids was rationalized.

Computing details

For all compounds, program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Figures

(lval_all) L-valine

Crystal data

C5H11NO2	Z = 4
Mr = 117.15	F(000) = 256
Monoclinic, P21	Dx = 1.265 Mg m^−3
a = 9.6697 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.2749 (9) Å	µ = 0.10 mm^−1
c = 12.063 (2) Å	T = 298 K
β = 90.803 (14)°	Trapezoid, clear light colourless
V = 615.22 (18) Å^3	0.35 × 0.25 × 0.1 mm

Data collection

Stoe IPDS II diffractometer	Rint = 0.042
rotation method scans	θmax = 26.4°, θmin = 1.7°
4649 measured reflections	h = −12→12
2516 independent reflections	k = −6→6
1333 reflections with I > 2σ(I)	l = −15→14

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.071	w = 1/[σ^2(Fo^2) + (0.0239P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.78	(Δ/σ)max < 0.001
2516 reflections	Δρmax = 0.13 e Å^−3
151 parameters	Δρmin = −0.15 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O22	0.3711 (2)	0.1644 (4)	0.39977 (19)	0.0383 (7)
O21	0.8556 (2)	0.5645 (4)	0.3966 (2)	0.0394 (7)
C11	0.7648 (3)	0.4087 (8)	0.3639 (3)	0.0360 (9)
O12	0.2912 (2)	−0.2055 (5)	0.3368 (2)	0.0430 (7)
O11	0.7737 (2)	0.1723 (5)	0.3689 (2)	0.0487 (7)
N21	0.1233 (3)	0.3785 (5)	0.4099 (2)	0.0339 (7)
H21A	0.1848	0.4892	0.3848	0.041*
H21B	0.1405	0.3473	0.4813	0.041*
H21C	0.0386	0.4426	0.4020	0.041*
N11	0.5889 (3)	0.7455 (5)	0.3753 (2)	0.0402 (9)
H11A	0.6413	0.8790	0.3596	0.048*
H11B	0.5968	0.7096	0.4472	0.048*
H11C	0.5010	0.7806	0.3586	0.048*
C22	0.1331 (3)	0.1384 (6)	0.3458 (3)	0.0315 (9)
H22	0.0646	0.0194	0.3747	0.038*
C12	0.2766 (3)	0.0235 (7)	0.3640 (3)	0.0333 (9)
C21	0.6349 (3)	0.5227 (6)	0.3088 (3)	0.0314 (9)
H21	0.5613	0.3950	0.3075	0.038*
C32	0.0981 (3)	0.1883 (7)	0.2233 (3)	0.0376 (9)
H32	0.0233	0.3138	0.2210	0.045*
C31	0.6640 (3)	0.6064 (7)	0.1899 (3)	0.0380 (10)
H31	0.7384	0.7324	0.1933	0.046*
C41	0.5402 (4)	0.7300 (9)	0.1337 (3)	0.0584 (13)
H41A	0.4666	0.6087	0.1266	0.088*
H41B	0.5657	0.7886	0.0615	0.088*
H41C	0.5098	0.8710	0.1774	0.088*
C52	0.0432 (4)	−0.0524 (8)	0.1662 (3)	0.0578 (13)
H52A	0.1162	−0.1750	0.1616	0.087*
H52B	0.0103	−0.0112	0.0929	0.087*
H52C	−0.0313	−0.1215	0.2084	0.087*
C42	0.2185 (4)	0.2989 (8)	0.1591 (3)	0.0507 (10)
H42A	0.2578	0.4382	0.1999	0.076*
H42B	0.1859	0.3574	0.0881	0.076*
H42C	0.2876	0.1706	0.1490	0.076*
C51	0.7145 (4)	0.3850 (9)	0.1203 (3)	0.0688 (14)
H51A	0.7942	0.3101	0.1556	0.103*
H51B	0.7388	0.4448	0.0480	0.103*
H51C	0.6425	0.2605	0.1136	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O22	0.0233 (11)	0.0426 (18)	0.0491 (17)	−0.0010 (11)	−0.0009 (11)	−0.0048 (14)
O21	0.0250 (12)	0.0412 (16)	0.0517 (17)	0.0021 (12)	−0.0070 (11)	−0.0086 (13)
C11	0.0282 (19)	0.044 (3)	0.036 (2)	0.007 (2)	0.0039 (16)	0.001 (2)
O12	0.0350 (13)	0.0300 (16)	0.0638 (18)	0.0074 (12)	0.0012 (12)	−0.0049 (14)
O11	0.0461 (15)	0.0304 (17)	0.0695 (19)	0.0073 (14)	−0.0040 (13)	0.0052 (16)
N21	0.0221 (14)	0.0352 (18)	0.0445 (19)	0.0067 (12)	0.0032 (13)	−0.0026 (16)
N11	0.0289 (15)	0.045 (2)	0.0471 (19)	0.0109 (15)	0.0011 (14)	0.0053 (17)
C22	0.0244 (16)	0.026 (2)	0.044 (2)	0.0005 (15)	0.0038 (15)	−0.0025 (18)
C12	0.0290 (19)	0.036 (2)	0.035 (2)	0.0071 (18)	0.0039 (16)	0.005 (2)
C21	0.0239 (16)	0.031 (2)	0.040 (2)	0.0012 (15)	−0.0005 (15)	−0.0021 (19)
C32	0.0297 (17)	0.040 (2)	0.043 (2)	0.0068 (16)	−0.0048 (16)	−0.002 (2)
C31	0.0300 (18)	0.043 (2)	0.041 (2)	0.0006 (17)	−0.0017 (17)	0.0066 (19)
C41	0.047 (2)	0.074 (3)	0.054 (3)	0.009 (2)	−0.006 (2)	0.021 (2)
C52	0.050 (2)	0.065 (3)	0.059 (3)	−0.003 (2)	−0.014 (2)	−0.009 (2)
C42	0.055 (2)	0.053 (3)	0.045 (2)	0.003 (2)	0.007 (2)	0.001 (2)
C51	0.079 (3)	0.080 (3)	0.047 (3)	0.019 (3)	0.000 (2)	−0.004 (3)

Geometric parameters (Å, º)

O22—C12	1.250 (4)	C32—H32	0.9800
O21—C11	1.262 (4)	C32—C52	1.536 (5)
C11—O11	1.251 (4)	C32—C42	1.523 (5)
C11—C21	1.536 (4)	C31—H31	0.9800
O12—C12	1.260 (4)	C31—C41	1.515 (5)
N21—H21A	0.8900	C31—C51	1.523 (5)
N21—H21B	0.8900	C41—H41A	0.9600
N21—H21C	0.8900	C41—H41B	0.9600
N21—C22	1.488 (4)	C41—H41C	0.9600
N11—H11A	0.8900	C52—H52A	0.9600
N11—H11B	0.8900	C52—H52B	0.9600
N11—H11C	0.8900	C52—H52C	0.9600
N11—C21	1.495 (4)	C42—H42A	0.9600
C22—H22	0.9800	C42—H42B	0.9600
C22—C12	1.527 (4)	C42—H42C	0.9600
C22—C32	1.534 (5)	C51—H51A	0.9600
C21—H21	0.9800	C51—H51B	0.9600
C21—C31	1.530 (5)	C51—H51C	0.9600
O21—C11—C21	116.2 (3)	C42—C32—C22	113.3 (3)
O11—C11—O21	126.0 (4)	C42—C32—H32	107.2
O11—C11—C21	117.8 (3)	C42—C32—C52	110.5 (3)
H21A—N21—H21B	109.5	C21—C31—H31	107.6
H21A—N21—H21C	109.5	C41—C31—C21	112.9 (3)
H21B—N21—H21C	109.5	C41—C31—H31	107.6
C22—N21—H21A	109.5	C41—C31—C51	109.9 (3)
C22—N21—H21B	109.5	C51—C31—C21	111.1 (3)
C22—N21—H21C	109.5	C51—C31—H31	107.6
H11A—N11—H11B	109.5	C31—C41—H41A	109.5
H11A—N11—H11C	109.5	C31—C41—H41B	109.5
H11B—N11—H11C	109.5	C31—C41—H41C	109.5
C21—N11—H11A	109.5	H41A—C41—H41B	109.5
C21—N11—H11B	109.5	H41A—C41—H41C	109.5
C21—N11—H11C	109.5	H41B—C41—H41C	109.5
N21—C22—H22	108.1	C32—C52—H52A	109.5
N21—C22—C12	109.1 (3)	C32—C52—H52B	109.5
N21—C22—C32	109.9 (3)	C32—C52—H52C	109.5
C12—C22—H22	108.1	H52A—C52—H52B	109.5
C12—C22—C32	113.3 (3)	H52A—C52—H52C	109.5
C32—C22—H22	108.1	H52B—C52—H52C	109.5
O22—C12—O12	125.2 (3)	C32—C42—H42A	109.5
O22—C12—C22	118.2 (3)	C32—C42—H42B	109.5
O12—C12—C22	116.6 (3)	C32—C42—H42C	109.5
C11—C21—H21	109.1	H42A—C42—H42B	109.5
N11—C21—C11	108.9 (3)	H42A—C42—H42C	109.5
N11—C21—H21	109.1	H42B—C42—H42C	109.5
N11—C21—C31	109.6 (3)	C31—C51—H51A	109.5
C31—C21—C11	111.0 (2)	C31—C51—H51B	109.5
C31—C21—H21	109.1	C31—C51—H51C	109.5
C22—C32—H32	107.2	H51A—C51—H51B	109.5
C22—C32—C52	111.1 (3)	H51A—C51—H51C	109.5
C52—C32—H32	107.2	H51B—C51—H51C	109.5
O21—C11—C21—N11	−43.9 (4)	N21—C22—C32—C52	−154.3 (3)
O21—C11—C21—C31	76.9 (4)	N21—C22—C32—C42	80.6 (3)
C11—C21—C31—C41	−177.6 (3)	N11—C21—C31—C41	−57.3 (4)
C11—C21—C31—C51	58.3 (4)	N11—C21—C31—C51	178.6 (3)
O11—C11—C21—N11	138.6 (3)	C12—C22—C32—C52	83.4 (3)
O11—C11—C21—C31	−100.6 (4)	C12—C22—C32—C42	−41.7 (4)
N21—C22—C12—O22	−18.8 (4)	C32—C22—C12—O22	103.9 (4)
N21—C22—C12—O12	164.2 (3)	C32—C22—C12—O12	−73.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21A···O12^i	0.89	2.00	2.876 (4)	167
N21—H21B···O21^ii	0.89	2.10	2.867 (4)	144
N21—H21C···O21^iii	0.89	1.88	2.771 (3)	175
N11—H11A···O11^i	0.89	2.01	2.876 (4)	164
N11—H11B···O22^iv	0.89	1.88	2.769 (4)	173
N11—H11C···O12^i	0.89	2.04	2.921 (3)	169

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

(lval_mal_all) L-valinium maleate

Crystal data

C5H12NO2·C4H3O4	Z = 2
Mr = 233.22	F(000) = 248
Monoclinic, P21	Dx = 1.368 Mg m^−3
a = 5.7793 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5974 (11) Å	µ = 0.12 mm^−1
c = 12.9136 (17) Å	T = 298 K
β = 93.13 (1)°	Block, clear light colourless
V = 566.16 (14) Å^3	0.3 × 0.2 × 0.1 mm

Data collection

STOE IPDS 2 diffractometer	1193 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.045
Plane graphite monochromator	θmax = 26.4°, θmin = 3.1°
Detector resolution: 6.67 pixels mm^-1	h = −5→7
rotation method scans	k = −9→9
3587 measured reflections	l = −16→16
2276 independent reflections

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.018P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.77	(Δ/σ)max < 0.001
2276 reflections	Δρmax = 0.13 e Å^−3
150 parameters	Δρmin = −0.16 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.3223 (5)	0.3591 (4)	0.44680 (17)	0.0422 (8)
H1	0.2148	0.3486	0.4031	0.063*
O3	0.0267 (5)	0.3265 (4)	1.29205 (16)	0.0437 (8)
C1	0.2549 (8)	0.4552 (6)	0.5245 (3)	0.0316 (11)
O4	0.3175 (5)	0.3019 (4)	1.18775 (19)	0.0468 (9)
O6	0.3904 (5)	0.3786 (6)	1.0053 (2)	0.0657 (11)
H6	0.3725	0.3564	1.0665	0.099*
O2	0.0696 (6)	0.5204 (4)	0.5311 (2)	0.0527 (9)
C6	0.1111 (7)	0.3384 (6)	1.2045 (3)	0.0341 (10)
O5	0.1894 (6)	0.4923 (5)	0.8738 (2)	0.0614 (11)
C2	0.4533 (7)	0.4789 (5)	0.6062 (3)	0.0292 (10)
H2	0.5804	0.5392	0.5735	0.035*
C8	−0.0145 (7)	0.4428 (6)	1.0220 (3)	0.0421 (13)
H8	−0.1455	0.4830	0.9842	0.051*
C3	0.5460 (7)	0.3034 (6)	0.6502 (3)	0.0361 (11)
H3	0.6230	0.2441	0.5941	0.043*
C7	−0.0514 (7)	0.3994 (6)	1.1189 (2)	0.0382 (12)
H7	−0.2049	0.4087	1.1363	0.046*
C9	0.1992 (8)	0.4387 (6)	0.9627 (3)	0.0427 (12)
C5	0.3538 (9)	0.1792 (6)	0.6836 (4)	0.0485 (13)
H5A	0.2752	0.2319	0.7394	0.073*
H5B	0.4211	0.0693	0.7064	0.073*
H5C	0.2452	0.1587	0.6259	0.073*
C4	0.7297 (7)	0.3326 (8)	0.7378 (3)	0.0555 (13)
H4A	0.8122	0.2247	0.7517	0.083*
H4B	0.6564	0.3697	0.7991	0.083*
H4C	0.8363	0.4217	0.7178	0.083*
N1	0.3700 (6)	0.5953 (4)	0.6890 (2)	0.0314 (9)
H1A	0.2594	0.6659	0.6623	0.038*
H1B	0.4875	0.6598	0.7155	0.038*
H1C	0.3134	0.5297	0.7388	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0484 (18)	0.048 (2)	0.0290 (14)	0.0048 (19)	−0.0053 (12)	−0.0101 (16)
O3	0.0480 (18)	0.059 (2)	0.0247 (13)	−0.0107 (18)	0.0013 (11)	0.0017 (16)
C1	0.044 (3)	0.027 (3)	0.0242 (19)	0.000 (2)	0.0009 (19)	0.002 (2)
O4	0.0323 (18)	0.067 (3)	0.0408 (15)	0.0081 (18)	−0.0022 (13)	0.0159 (16)
O6	0.0369 (19)	0.114 (3)	0.0475 (17)	0.014 (2)	0.0143 (14)	0.024 (2)
O2	0.043 (2)	0.072 (3)	0.0417 (18)	0.019 (2)	−0.0099 (15)	−0.0155 (17)
C6	0.044 (3)	0.029 (3)	0.029 (2)	−0.008 (3)	−0.0038 (18)	−0.001 (2)
O5	0.071 (2)	0.086 (3)	0.0274 (15)	0.007 (2)	0.0116 (14)	0.0144 (19)
C2	0.032 (2)	0.032 (3)	0.0245 (18)	−0.003 (2)	0.0054 (16)	−0.005 (2)
C8	0.031 (3)	0.064 (4)	0.031 (2)	0.003 (2)	−0.0026 (18)	0.003 (2)
C3	0.036 (2)	0.037 (3)	0.036 (2)	0.004 (2)	0.0053 (19)	0.000 (2)
C7	0.029 (2)	0.055 (3)	0.030 (2)	0.004 (2)	−0.0022 (16)	−0.002 (2)
C9	0.046 (3)	0.044 (4)	0.038 (2)	−0.002 (3)	0.004 (2)	−0.001 (2)
C5	0.056 (4)	0.038 (3)	0.051 (3)	−0.001 (3)	0.000 (2)	0.005 (2)
C4	0.040 (3)	0.065 (4)	0.060 (3)	0.010 (3)	−0.015 (2)	0.001 (3)
N1	0.030 (2)	0.033 (2)	0.0307 (18)	−0.0009 (18)	−0.0030 (16)	−0.0030 (16)

Geometric parameters (Å, º)

O1—H1	0.8200	C8—C9	1.489 (5)
O1—C1	1.317 (4)	C3—H3	0.9800
O3—C6	1.259 (4)	C3—C5	1.538 (6)
C1—O2	1.187 (5)	C3—C4	1.525 (5)
C1—C2	1.526 (5)	C7—H7	0.9300
O4—C6	1.255 (4)	C5—H5A	0.9600
O6—H6	0.8200	C5—H5B	0.9600
O6—C9	1.291 (5)	C5—H5C	0.9600
C6—C7	1.485 (5)	C4—H4A	0.9600
O5—C9	1.216 (4)	C4—H4B	0.9600
C2—H2	0.9800	C4—H4C	0.9600
C2—C3	1.534 (5)	N1—H1A	0.8900
C2—N1	1.488 (4)	N1—H1B	0.8900
C8—H8	0.9300	N1—H1C	0.8900
C8—C7	1.321 (5)
C1—O1—H1	109.5	C8—C7—C6	130.8 (4)
O1—C1—C2	110.5 (4)	C8—C7—H7	114.6
O2—C1—O1	126.3 (4)	O6—C9—C8	120.2 (3)
O2—C1—C2	123.2 (4)	O5—C9—O6	121.0 (4)
C9—O6—H6	109.5	O5—C9—C8	118.8 (4)
O3—C6—C7	115.5 (4)	C3—C5—H5A	109.5
O4—C6—O3	123.8 (4)	C3—C5—H5B	109.5
O4—C6—C7	120.6 (3)	C3—C5—H5C	109.5
C1—C2—H2	108.1	H5A—C5—H5B	109.5
C1—C2—C3	112.8 (3)	H5A—C5—H5C	109.5
C3—C2—H2	108.1	H5B—C5—H5C	109.5
N1—C2—C1	107.9 (3)	C3—C4—H4A	109.5
N1—C2—H2	108.1	C3—C4—H4B	109.5
N1—C2—C3	111.7 (3)	C3—C4—H4C	109.5
C7—C8—H8	114.2	H4A—C4—H4B	109.5
C7—C8—C9	131.5 (4)	H4A—C4—H4C	109.5
C9—C8—H8	114.2	H4B—C4—H4C	109.5
C2—C3—H3	106.8	C2—N1—H1A	109.5
C2—C3—C5	113.2 (4)	C2—N1—H1B	109.5
C5—C3—H3	106.8	C2—N1—H1C	109.5
C4—C3—C2	111.3 (4)	H1A—N1—H1B	109.5
C4—C3—H3	106.8	H1A—N1—H1C	109.5
C4—C3—C5	111.4 (3)	H1B—N1—H1C	109.5
C6—C7—H7	114.6
O1—C1—C2—C3	−58.8 (4)	O2—C1—C2—N1	−0.7 (5)
O1—C1—C2—N1	177.3 (3)	C7—C8—C9—O6	2.9 (8)
O3—C6—C7—C8	172.2 (5)	C7—C8—C9—O5	−177.4 (5)
C1—C2—C3—C5	−48.8 (5)	C9—C8—C7—C6	3.1 (8)
C1—C2—C3—C4	−175.2 (3)	N1—C2—C3—C5	72.9 (4)
O4—C6—C7—C8	−7.9 (7)	N1—C2—C3—C4	−53.5 (4)
O2—C1—C2—C3	123.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.82	1.76	2.569 (3)	169
O6—H6···O4	0.82	1.67	2.485 (4)	175
N1—H1A···O3^ii	0.89	2.16	2.909 (4)	141
N1—H1B···O4^iii	0.89	1.96	2.819 (4)	161
N1—H1C···O5	0.89	1.94	2.770 (4)	154

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

(maleicacid) maleic acid

Crystal data

C4H4O4	Z = 4
Mr = 116.07	F(000) = 240
Monoclinic, P21/c	Dx = 1.602 Mg m^−3
a = 7.1511 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1107 (11) Å	µ = 0.15 mm^−1
c = 7.6405 (10) Å	T = 298 K
β = 119.405 (8)°	Block, clear light colourless
V = 481.26 (10) Å^3	0.25 × 0.2 × 0.15 mm

Data collection

STOE IPDS II diffractometer	541 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.071
Plane graphite monochromator	θmax = 26.4°, θmin = 3.3°
Detector resolution: 6.67 pixels mm^-1	h = −8→7
rotation method scans	k = −12→12
3499 measured reflections	l = −9→9
979 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0615P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.84	(Δ/σ)max < 0.001
979 reflections	Δρmax = 0.16 e Å^−3
75 parameters	Δρmin = −0.21 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O3	0.4657 (3)	0.77059 (13)	0.7214 (2)	0.0652 (5)
O2	−0.1085 (3)	0.74614 (16)	0.1414 (2)	0.0716 (5)
O4	0.6192 (3)	0.58072 (14)	0.8643 (2)	0.0687 (5)
H4	0.7057	0.6309	0.9504	0.103*
O1	0.1500 (3)	0.84393 (12)	0.3991 (2)	0.0633 (5)
H1	0.2568	0.8244	0.5054	0.095*
C2	0.1375 (3)	0.60370 (19)	0.3892 (3)	0.0525 (6)
H2	0.0557	0.5339	0.3088	0.063*
C3	0.3075 (3)	0.56624 (19)	0.5584 (3)	0.0537 (6)
H3	0.3275	0.4754	0.5782	0.064*
C4	0.4690 (3)	0.6497 (2)	0.7193 (3)	0.0523 (6)
C1	0.0527 (3)	0.7361 (2)	0.3035 (3)	0.0524 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0639 (10)	0.0337 (8)	0.0597 (10)	−0.0006 (7)	0.0007 (8)	−0.0025 (7)
O2	0.0621 (10)	0.0527 (10)	0.0569 (9)	0.0006 (8)	−0.0042 (8)	−0.0003 (7)
O4	0.0623 (11)	0.0415 (8)	0.0592 (10)	0.0048 (8)	−0.0034 (8)	0.0030 (8)
O1	0.0628 (11)	0.0340 (8)	0.0558 (9)	−0.0011 (7)	0.0002 (8)	0.0006 (7)
C2	0.0528 (13)	0.0332 (10)	0.0528 (12)	−0.0066 (9)	0.0115 (11)	−0.0062 (9)
C3	0.0547 (13)	0.0307 (10)	0.0561 (13)	−0.0011 (10)	0.0121 (11)	−0.0024 (9)
C4	0.0523 (13)	0.0366 (11)	0.0513 (12)	0.0036 (10)	0.0126 (11)	0.0032 (10)
C1	0.0476 (12)	0.0427 (11)	0.0468 (12)	0.0000 (10)	0.0076 (11)	−0.0007 (10)

Geometric parameters (Å, º)

O3—C4	1.223 (2)	C2—H2	0.9300
O2—C1	1.213 (2)	C2—C3	1.323 (3)
O4—H4	0.8200	C2—C1	1.482 (3)
O4—C4	1.304 (2)	C3—H3	0.9300
O1—H1	0.8200	C3—C4	1.470 (3)
O1—C1	1.307 (2)
C4—O4—H4	109.5	C4—C3—H3	115.8
C1—O1—H1	109.5	O3—C4—O4	122.44 (18)
C3—C2—H2	114.0	O3—C4—C3	124.93 (19)
C3—C2—C1	132.09 (18)	O4—C4—C3	112.63 (17)
C1—C2—H2	114.0	O2—C1—O1	118.61 (18)
C2—C3—H3	115.8	O2—C1—C2	120.27 (19)
C2—C3—C4	128.35 (19)	O1—C1—C2	121.11 (17)
C2—C3—C4—O3	1.9 (4)	C3—C2—C1—O1	−0.1 (4)
C2—C3—C4—O4	−178.7 (2)	C1—C2—C3—C4	0.5 (4)
C3—C2—C1—O2	179.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2^i	0.82	1.83	2.650 (2)	178
O1—H1···O3	0.82	1.68	2.500 (2)	175

Symmetry code: (i) x+1, y, z+1.