A 2-propanol solvate of (RS)-phenyl­succinic acid

A solvate of (RS)-phenyl­succinic acid (RS-PSA) has been obtained from 2-propanol (IPA). The compound, C₁₀H₁₀O₄·C₃H₈O, crystallizes in the monoclinic crystal system (space group C2/c). It features mol­ecules of the S form of the acid, one of whose carboxy groups is connected to one carboxy group of a mol­ecule of the opposite chirality via two hydrogen bonds. The second carboxy group of the S mol­ecule is connected to two other S mol­ecules via the OH groups of two 2-propanol solvent mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.058
• wR factor = 0.131
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT390_ALERT_3_C Deviating Methyl C13     X-C-H Bond Angle ......     116.05 Deg.
PLAT391_ALERT_3_C Deviating Methyl C13     H-C-H Bond Angle ......     100.94 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DORAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: maXus (Mackay et al., 1999).

(I)

Crystal data

C10H10O4·C3H8O	Z = 8
Mr = 254.28	Dx = 1.310 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 87 reflections
a = 26.46 (1) Å	θ = 4.6–27.5°
b = 5.467 (2) Å	µ = 0.10 mm^−1
c = 21.477 (6) Å	T = 150 K
β = 123.93 (3)°	Block, colourless
V = 2577.8 (18) Å^3	0.40 × 0.20 × 0.15 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	Rint = 0.083
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 4.6°
φ and ω scans	h = −32→34
9953 measured reflections	k = −5→7
2904 independent reflections	l = −27→27
1868 reflections with I > 2σ(I)

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)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0296P)^2 + 5.2191P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2904 reflections	Δρmax = 0.29 e Å^−3
163 parameters	Δρmin = −0.24 e Å^−3
0 restraints

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.

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

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

	x	y	z	Uiso*/Ueq
C1	0.06370 (9)	0.3862 (5)	0.36450 (11)	0.0170 (5)
C2	0.06261 (10)	0.5824 (5)	0.40512 (12)	0.0208 (5)
C3	0.01926 (11)	0.5926 (5)	0.42248 (13)	0.0243 (5)
C4	−0.02339 (11)	0.4086 (5)	0.39911 (13)	0.0256 (6)
C5	−0.02184 (10)	0.2102 (5)	0.36020 (13)	0.0244 (5)
O5	0.20871 (7)	0.9047 (4)	0.18904 (9)	0.0297 (4)
C6	0.02158 (10)	0.1993 (5)	0.34316 (12)	0.0209 (5)
C7	0.10902 (9)	0.3797 (4)	0.34211 (11)	0.0171 (5)
C8	0.17189 (10)	0.3283 (4)	0.41117 (12)	0.0174 (5)
C9	0.10704 (10)	0.6173 (5)	0.30385 (12)	0.0191 (5)
C10	0.14661 (9)	0.6170 (5)	0.27371 (11)	0.0182 (5)
C11	0.19829 (13)	0.5668 (6)	0.11004 (16)	0.0398 (7)
C12	0.18594 (11)	0.8355 (5)	0.11298 (13)	0.0268 (6)
C13	0.11943 (12)	0.8978 (6)	0.06612 (14)	0.0348 (7)
O1	0.17908 (7)	0.0979 (3)	0.43163 (9)	0.0264 (4)
O2	0.21051 (7)	0.4850 (3)	0.44506 (9)	0.0246 (4)
O3	0.14622 (7)	0.8326 (3)	0.24652 (9)	0.0264 (4)
O4	0.17434 (7)	0.4404 (3)	0.27452 (9)	0.0278 (4)
H1O	0.2170	0.0693	0.4703	0.032*
H2	0.0935	0.6932	0.4219	0.025*
H3	0.0196	0.7409	0.4501	0.029*
H3O	0.1715	0.8269	0.2280	0.032*
H4	−0.0550	0.4098	0.4085	0.031*
H5	−0.0547	0.0965	0.3396	0.029*
H5O	0.2514	0.9148	0.2113	0.036*
H6	0.0264	0.0604	0.3162	0.025*
H7	0.0998	0.2486	0.3086	0.021*
H9A	0.1174	0.7575	0.3394	0.023*
H9B	0.0641	0.6299	0.2585	0.023*
H11A	0.2432	0.5449	0.1410	0.048*
H11B	0.1832	0.5041	0.0595	0.048*
H11C	0.1748	0.4727	0.1312	0.048*
H12	0.2101	0.9304	0.1000	0.032*
H13A	0.1039	0.8599	0.0135	0.042*
H13B	0.1138	1.0784	0.0693	0.042*
H13C	0.0948	0.8302	0.0832	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0128 (9)	0.0209 (13)	0.0133 (10)	0.0021 (9)	0.0049 (8)	0.0052 (9)
C2	0.0176 (11)	0.0220 (13)	0.0199 (11)	−0.0008 (10)	0.0087 (9)	0.0010 (10)
C3	0.0261 (12)	0.0243 (14)	0.0265 (12)	0.0039 (11)	0.0171 (10)	0.0033 (10)
C4	0.0195 (11)	0.0327 (16)	0.0285 (12)	0.0046 (11)	0.0157 (10)	0.0067 (11)
C5	0.0185 (11)	0.0256 (14)	0.0248 (12)	−0.0031 (10)	0.0094 (10)	0.0052 (10)
C6	0.0187 (11)	0.0199 (13)	0.0197 (11)	0.0002 (10)	0.0081 (9)	0.0018 (10)
C7	0.0142 (10)	0.0184 (13)	0.0171 (10)	−0.0003 (9)	0.0078 (8)	−0.0003 (9)
C8	0.0175 (11)	0.0181 (12)	0.0187 (10)	0.0020 (10)	0.0114 (9)	0.0006 (9)
C9	0.0157 (10)	0.0227 (13)	0.0178 (10)	0.0019 (10)	0.0086 (9)	0.0027 (9)
C10	0.0120 (10)	0.0230 (13)	0.0160 (10)	−0.0004 (10)	0.0056 (8)	0.0012 (9)
C11	0.0352 (14)	0.042 (2)	0.0324 (14)	0.0063 (14)	0.0130 (12)	−0.0033 (13)
C12	0.0243 (12)	0.0345 (16)	0.0222 (11)	−0.0034 (12)	0.0134 (10)	−0.0009 (11)
C13	0.0267 (13)	0.0389 (18)	0.0296 (13)	0.0013 (13)	0.0101 (11)	−0.0015 (12)
O1	0.0194 (8)	0.0198 (10)	0.0246 (8)	0.0016 (7)	0.0028 (7)	0.0053 (7)
O2	0.0172 (8)	0.0228 (10)	0.0236 (8)	−0.0025 (7)	0.0050 (7)	0.0010 (7)
O3	0.0271 (9)	0.0264 (11)	0.0350 (9)	0.0043 (8)	0.0231 (8)	0.0076 (8)
O4	0.0249 (8)	0.0263 (11)	0.0375 (10)	0.0057 (8)	0.0207 (8)	0.0035 (8)
O5	0.0204 (8)	0.0479 (13)	0.0246 (8)	−0.0083 (9)	0.0148 (7)	−0.0047 (8)

Geometric parameters (Å, º)

O5—C12	1.441 (3)	C12—H12	0.9770
C12—C13	1.500 (3)	C13—H13A	0.9857
C12—C11	1.514 (4)	C13—H13B	1.0064
O1—C8	1.312 (3)	C13—H13C	0.9810
O2—C8	1.216 (3)	C11—H11A	0.9927
O3—C10	1.313 (3)	C11—H11B	0.9851
O4—C10	1.207 (3)	C11—H11C	1.0837
C10—C9	1.508 (3)	O1—H1O	0.8898
C7—C8	1.514 (3)	O3—H3O	0.9500
C7—C1	1.521 (3)	C7—H7	0.9461
C7—C9	1.522 (3)	C9—H9A	1.0051
C1—C6	1.388 (3)	C9—H9B	1.0044
C1—C2	1.393 (3)	C2—H2	0.9140
C2—C3	1.391 (3)	C3—H3	1.0018
C3—C4	1.380 (4)	C6—H6	1.0053
C6—C5	1.388 (3)	C5—H5	0.9530
C5—C4	1.384 (4)	C4—H4	0.9648
O5—H5O	0.9508
O5—C12—C13	107.0 (2)	H13A—C13—H13C	114.3
O5—C12—C11	109.8 (2)	H13B—C13—H13C	101.0
C13—C12—C11	113.1 (2)	C12—C11—H11A	107.1
O4—C10—O3	125.4 (2)	C12—C11—H11B	114.8
O4—C10—C9	123.9 (2)	H11A—C11—H11B	107.1
O3—C10—C9	110.8 (2)	C12—C11—H11C	104.8
C8—C7—C1	108.89 (16)	H11A—C11—H11C	114.5
C8—C7—C9	112.03 (19)	H11B—C11—H11C	108.8
C1—C7—C9	110.78 (19)	C8—O1—H1O	111.0
C6—C1—C2	118.7 (2)	C10—O3—H3O	108.9
C6—C1—C7	120.5 (2)	C8—C7—H7	106.3
C2—C1—C7	120.8 (2)	C1—C7—H7	110.2
C10—C9—C7	114.1 (2)	C9—C7—H7	108.6
O2—C8—O1	124.0 (2)	C10—C9—H9A	111.5
O2—C8—C7	123.5 (2)	C7—C9—H9A	109.2
O1—C8—C7	112.4 (2)	C10—C9—H9B	105.3
C3—C2—C1	120.5 (2)	C7—C9—H9B	105.2
C4—C3—C2	120.2 (2)	H9A—C9—H9B	111.5
C1—C6—C5	120.8 (2)	C3—C2—H2	123.9
C4—C5—C6	120.0 (2)	C1—C2—H2	115.5
C3—C4—C5	119.8 (2)	C4—C3—H3	122.7
C12—O5—H5O	102.3	C2—C3—H3	117.1
O5—C12—H12	104.9	C1—C6—H6	114.2
C13—C12—H12	113.5	C5—C6—H6	125.0
C11—C12—H12	108.2	C4—C5—H5	117.7
C12—C13—H13A	107.7	C6—C5—H5	121.6
C12—C13—H13B	109.9	C3—C4—H4	123.2
H13A—C13—H13B	107.5	C5—C4—H4	117.0
C12—C13—H13C	116.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	0.89	1.78	2.668 (2)	173
O3—H3O···O5	0.95	1.67	2.587 (2)	163
O5—H5O···O4^ii	0.95	1.82	2.743 (2)	163

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