(S)-Phenyl­succinic acid

(S)-Phenyl­succinic acid, C₁₀H₁₀O₄, crystallizes from water with two mol­ecules per asymmetric unit. In the crystal structure, the carboxyl groups of each acid mol­ecule are connected to those of adjacent mol­ecules via hydrogen bonds; each mol­ecule is connected to three other mol­ecules, forming infinite chains.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.074
• Data-to-parameter ratio = 8.5

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.44
         From the CIF: _reflns_number_total               2162
         Count of symmetry unique reflns         2177
         Completeness (_total/calc)             99.31%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: HKL SCALEPACK (Otwinowski et al., 1997); data reduction: HKL SCALEPACK; 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., 1998).

(S)-phenylsuccinic acid

Crystal data

C10H10O4	Z = 4
Mr = 194.19	Dx = 1.396 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4591 reflections
a = 5.4193 (2) Å	θ = 4.1–27.5°
b = 18.0847 (5) Å	µ = 0.11 mm^−1
c = 9.4713 (3) Å	T = 100 K
β = 95.7044 (11)°	Irregular, colourless
V = 923.65 (5) Å^3	0.35 × 0.15 × 0.07 mm

Data collection

Bruker Nonius KappaCCD diffractometer	Rint = 0.037
Radiation source: fine-focus sealed tube	θmax = 27.4°, θmin = 4.2°
φ and ω scans	h = −7→6
7099 measured reflections	k = −22→23
2162 independent reflections	l = −12→12
2009 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)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.074	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 0.1504P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2162 reflections	Δρmax = 0.19 e Å^−3
253 parameters	Δρmin = −0.18 e Å^−3
1 restraint

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	0.4762 (4)	0.23618 (11)	−0.0045 (2)	0.0152 (4)
C2	0.5605 (3)	0.29248 (10)	0.1093 (2)	0.0139 (4)
C3	0.8263 (4)	0.28149 (10)	0.1743 (2)	0.0141 (4)
C4	0.8765 (3)	0.20843 (11)	0.2483 (2)	0.0148 (4)
C5	0.5291 (4)	0.36933 (11)	0.0435 (2)	0.0150 (4)
C6	0.6893 (4)	0.39420 (11)	−0.0537 (2)	0.0184 (4)
C7	0.6660 (4)	0.46497 (12)	−0.1090 (2)	0.0234 (5)
C8	0.4808 (4)	0.51209 (12)	−0.0694 (2)	0.0248 (5)
C9	0.3190 (4)	0.48742 (12)	0.0239 (2)	0.0234 (5)
C10	0.3419 (4)	0.41651 (11)	0.0802 (2)	0.0187 (4)
C11	0.5786 (3)	0.54050 (10)	0.5303 (2)	0.0149 (4)
C12	0.6135 (4)	0.48222 (10)	0.4193 (2)	0.0140 (4)
C13	0.8085 (4)	0.50882 (10)	0.3240 (2)	0.0156 (4)
C14	0.7388 (3)	0.58116 (10)	0.2531 (2)	0.0146 (4)
C15	0.6858 (4)	0.40833 (10)	0.4904 (2)	0.0152 (4)
C16	0.5249 (4)	0.34847 (11)	0.4744 (2)	0.0193 (4)
C17	0.5906 (4)	0.28060 (11)	0.5363 (2)	0.0248 (5)
C18	0.8171 (4)	0.27243 (12)	0.6165 (2)	0.0264 (5)
C19	0.9772 (4)	0.33220 (13)	0.6347 (2)	0.0247 (5)
C20	0.9131 (4)	0.40013 (11)	0.5723 (2)	0.0193 (4)
O1	0.6543 (2)	0.20405 (8)	−0.06541 (15)	0.0177 (3)
O2	0.2555 (3)	0.22477 (8)	−0.03780 (16)	0.0231 (3)
O3	1.1129 (3)	0.20283 (8)	0.29570 (16)	0.0234 (3)
O4	0.7194 (3)	0.16167 (8)	0.26223 (15)	0.0181 (3)
O5	0.3465 (2)	0.54763 (8)	0.55916 (15)	0.0185 (3)
O6	0.7527 (3)	0.57548 (8)	0.58740 (15)	0.0200 (3)
O7	0.9098 (2)	0.60695 (8)	0.17683 (15)	0.0199 (3)
O8	0.5420 (3)	0.61259 (8)	0.26567 (15)	0.0191 (3)
H2	0.4275	0.2816	0.1887	0.017*
H3A	0.8658	0.3212	0.2429	0.017*
H3B	0.9416	0.2833	0.1039	0.017*
H6	0.8184	0.3590	−0.0855	0.022*
H7	0.7772	0.4820	−0.1748	0.028*
H8	0.4723	0.5596	−0.1093	0.030*
H9	0.2022	0.5240	0.0598	0.028*
H10	0.2215	0.4007	0.1469	0.022*
H12	0.4506	0.4740	0.3687	0.017*
H13A	0.9729	0.5152	0.3805	0.019*
H13B	0.8055	0.4710	0.2494	0.019*
H16	0.3826	0.3525	0.4083	0.023*
H17	0.4690	0.2367	0.5339	0.030*
H18	0.8513	0.2237	0.6593	0.032*
H19	1.1469	0.3277	0.7008	0.030*
H20	1.0185	0.4428	0.5953	0.023*
H1O	0.5957	0.1757	−0.1417	0.021*
H3O	1.1544	0.1574	0.3352	0.028*
H5O	0.3270	0.5860	0.6164	0.022*
H7O	0.8549	0.6481	0.1268	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0150 (9)	0.0135 (8)	0.0173 (9)	0.0012 (7)	0.0020 (7)	0.0008 (7)
C2	0.0150 (9)	0.0128 (9)	0.0140 (9)	0.0000 (7)	0.0024 (7)	0.0002 (7)
C3	0.0154 (9)	0.0105 (8)	0.0162 (9)	−0.0021 (7)	0.0008 (7)	0.0009 (7)
C4	0.0150 (9)	0.0156 (9)	0.0141 (9)	−0.0004 (8)	0.0020 (7)	−0.0012 (7)
C5	0.0157 (9)	0.0144 (9)	0.0143 (9)	0.0011 (7)	−0.0022 (7)	−0.0010 (8)
C6	0.0224 (10)	0.0166 (10)	0.0164 (9)	0.0031 (8)	0.0025 (8)	0.0002 (8)
C7	0.0324 (12)	0.0192 (10)	0.0186 (10)	0.0007 (9)	0.0020 (9)	0.0055 (9)
C8	0.0334 (12)	0.0165 (9)	0.0230 (11)	0.0027 (9)	−0.0055 (9)	0.0018 (8)
C9	0.0242 (10)	0.0178 (10)	0.0267 (11)	0.0068 (8)	−0.0049 (9)	−0.0049 (9)
C10	0.0164 (9)	0.0190 (9)	0.0202 (10)	0.0015 (8)	−0.0009 (7)	−0.0035 (9)
C11	0.0164 (9)	0.0132 (9)	0.0151 (9)	0.0010 (7)	0.0013 (7)	0.0021 (7)
C12	0.0138 (9)	0.0126 (9)	0.0156 (9)	−0.0006 (7)	0.0015 (7)	−0.0012 (7)
C13	0.0162 (9)	0.0141 (9)	0.0165 (9)	0.0023 (7)	0.0016 (7)	0.0000 (7)
C14	0.0161 (10)	0.0136 (9)	0.0138 (9)	−0.0006 (7)	0.0001 (7)	−0.0001 (7)
C15	0.0184 (9)	0.0134 (9)	0.0146 (9)	0.0020 (7)	0.0060 (7)	−0.0015 (7)
C16	0.0214 (10)	0.0177 (10)	0.0194 (10)	−0.0018 (8)	0.0058 (8)	−0.0014 (8)
C17	0.0365 (12)	0.0155 (10)	0.0244 (11)	−0.0041 (9)	0.0125 (9)	−0.0007 (9)
C18	0.0363 (13)	0.0181 (10)	0.0273 (11)	0.0089 (9)	0.0162 (10)	0.0070 (9)
C19	0.0234 (11)	0.0283 (11)	0.0239 (11)	0.0084 (9)	0.0092 (9)	0.0086 (9)
C20	0.0189 (9)	0.0183 (10)	0.0214 (10)	0.0018 (8)	0.0050 (8)	0.0026 (8)
O1	0.0140 (6)	0.0191 (7)	0.0203 (7)	−0.0013 (5)	0.0038 (5)	−0.0070 (6)
O2	0.0140 (7)	0.0240 (8)	0.0311 (8)	−0.0001 (6)	0.0009 (6)	−0.0115 (7)
O3	0.0165 (7)	0.0174 (7)	0.0347 (8)	−0.0001 (6)	−0.0045 (6)	0.0113 (6)
O4	0.0192 (7)	0.0144 (6)	0.0207 (7)	−0.0034 (6)	0.0020 (6)	0.0032 (6)
O5	0.0151 (7)	0.0192 (7)	0.0217 (7)	−0.0001 (6)	0.0042 (5)	−0.0051 (6)
O6	0.0163 (7)	0.0185 (7)	0.0248 (7)	−0.0022 (5)	−0.0003 (6)	−0.0061 (6)
O7	0.0170 (7)	0.0193 (7)	0.0240 (7)	0.0020 (6)	0.0046 (6)	0.0070 (6)
O8	0.0184 (7)	0.0180 (7)	0.0215 (7)	0.0052 (6)	0.0044 (5)	0.0041 (6)

Geometric parameters (Å, º)

C1—O2	1.224 (2)	C16—C17	1.391 (3)
C1—O1	1.309 (2)	C17—C18	1.385 (3)
C1—C2	1.519 (3)	C18—C19	1.386 (3)
C2—C3	1.522 (3)	C19—C20	1.392 (3)
C2—C5	1.526 (3)	C2—H2	1.1097
C3—C4	1.508 (3)	C3—H3A	0.9776
C4—O4	1.216 (2)	C3—H3B	0.9586
C4—O3	1.318 (2)	C6—H6	1.0135
C5—C10	1.396 (3)	C7—H7	0.9601
C5—C6	1.400 (3)	C8—H8	0.9378
C6—C7	1.384 (3)	C9—H9	0.9985
C7—C8	1.396 (3)	C10—H10	0.9941
C8—C9	1.380 (3)	C12—H12	0.9731
C9—C10	1.390 (3)	C13—H13A	0.9993
C11—O6	1.217 (2)	C13—H13B	0.9818
C11—O5	1.320 (2)	C16—H16	0.9465
C11—C12	1.514 (3)	C17—H17	1.0306
C12—C15	1.530 (3)	C18—H18	0.9795
C12—C13	1.533 (3)	C19—H19	1.0629
C13—C14	1.502 (3)	C20—H20	0.9722
C14—O8	1.225 (2)	O1—H1O	0.9167
C14—O7	1.316 (2)	O3—H3O	0.9207
C15—C16	1.389 (3)	O5—H5O	0.8935
C15—C20	1.397 (3)	O7—H7O	0.9150
O2—C1—O1	123.78 (18)	C5—C2—H2	112.6
O2—C1—C2	120.87 (18)	C4—C3—H3A	108.5
O1—C1—C2	115.31 (16)	C2—C3—H3A	108.0
C1—C2—C3	113.90 (16)	C4—C3—H3B	104.7
C1—C2—C5	107.89 (15)	C2—C3—H3B	111.7
C3—C2—C5	110.29 (15)	H3A—C3—H3B	108.8
C4—C3—C2	114.97 (15)	C7—C6—H6	120.5
O4—C4—O3	125.21 (18)	C5—C6—H6	119.0
O4—C4—C3	124.32 (17)	C6—C7—H7	120.2
O3—C4—C3	110.47 (16)	C8—C7—H7	119.6
C10—C5—C6	118.72 (18)	C9—C8—H8	123.1
C10—C5—C2	120.62 (18)	C7—C8—H8	117.3
C6—C5—C2	120.65 (17)	C8—C9—H9	117.9
C7—C6—C5	120.44 (19)	C10—C9—H9	121.1
C6—C7—C8	120.3 (2)	C9—C10—H10	118.0
C9—C8—C7	119.6 (2)	C5—C10—H10	121.4
C8—C9—C10	120.4 (2)	C11—C12—H12	106.1
C9—C10—C5	120.5 (2)	C15—C12—H12	105.3
O6—C11—O5	124.74 (18)	C13—C12—H12	113.7
O6—C11—C12	121.70 (17)	C14—C13—H13A	108.1
O5—C11—C12	113.54 (16)	C12—C13—H13A	110.5
C11—C12—C15	110.31 (15)	C14—C13—H13B	107.4
C11—C12—C13	109.35 (15)	C12—C13—H13B	104.0
C15—C12—C13	111.84 (15)	H13A—C13—H13B	114.6
C14—C13—C12	112.29 (15)	C15—C16—H16	118.3
O8—C14—O7	123.81 (17)	C17—C16—H16	120.2
O8—C14—C13	122.93 (17)	C18—C17—H17	117.4
O7—C14—C13	113.26 (16)	C16—C17—H17	122.3
C16—C15—C20	119.14 (17)	C17—C18—H18	116.3
C16—C15—C12	120.19 (17)	C19—C18—H18	124.0
C20—C15—C12	120.67 (17)	C18—C19—H19	120.5
C15—C16—C17	120.69 (19)	C20—C19—H19	118.8
C18—C17—C16	120.0 (2)	C19—C20—H20	119.3
C17—C18—C19	119.63 (19)	C15—C20—H20	120.4
C18—C19—C20	120.6 (2)	C1—O1—H1O	112.5
C19—C20—C15	119.90 (19)	C4—O3—H3O	113.4
C1—C2—H2	101.1	C11—O5—H5O	112.0
C3—C2—H2	110.8	C14—O7—H7O	111.2

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O8^i	0.92	1.75	2.659 (2)	170
O3—H3O···O6^ii	0.92	1.71	2.627 (2)	177
O5—H5O···O4^iii	0.89	1.82	2.714 (2)	178
O7—H7O···O2^iv	0.92	1.70	2.615 (2)	178

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