Intermolecular hydrogen bonding in (2S)-2-(1-oxo-1H-2,3-di­hydro­isoindol-2-yl)­propanoic acid

The title compound, C₁₁H₁₁NO₃, a condensation product of L-alanine and ortho-phthal­aldehyde, crystallizes in space group P2₁2₁2₁. Intermolecular O—H...O=C and C—H...O hydrogen bonds are present with O...O and C...O distances of 2.623 (3) and 3.338 (4) Å, respectively.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.087
• Data-to-parameter ratio = 7.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.40
         From the CIF: _reflns_number_total               1086
         Count of symmetry unique reflns         1080
         Completeness (_total/calc)            100.56%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         6
         Fraction of Friedel pairs measured     0.006
         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.

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Computing details

Data collection: CAD4 (Enraf-Nonius, 1992); cell refinement: SET4 and CELDIM (Enraf-Nonius, 1992); data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).

2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid

Crystal data

C11H11NO3	Dx = 1.403 Mg m^−3
Mr = 205.21	Melting point: 485 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 5.1787 (5) Å	θ = 9.0–18.9°
b = 9.9128 (18) Å	µ = 0.10 mm^−1
c = 18.918 (5) Å	T = 294 K
V = 971.2 (3) Å^3	Plate, colourless
Z = 4	0.42 × 0.21 × 0.04 mm
F(000) = 432

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.024
Radiation source: X-ray tube	θmax = 25.4°, θmin = 2.1°
Graphite monochromator	h = −6→6
ω–2θ scans	k = −11→11
1803 measured reflections	l = −22→22
1086 independent reflections	3 standard reflections every 240 min
866 reflections with I > 2σ(I)	intensity decay: 0.5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0513P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
1086 reflections	Δρmax = 0.15 e Å^−3
139 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (3)

Special details

Geometry. Mean plane data ex-SHELXL97 for molecule (I) ############################################

-3.5683(0.0045)x + 6.8741(0.0085)y + 3.9846(0.0239)z = 2.4843(0.0240)

* 0.0011 (0.0018) C4 * 0.0010 (0.0020) C5 * -0.0020 (0.0022) C6 * 0.0009 (0.0022) C7 * 0.0011 (0.0021) C8 * -0.0021 (0.0019) C9 0.0349 (0.0046) N1 0.1198 (0.0052) O3 0.0496 (0.0044) C3 0.0324 (0.0042) C10

Rms deviation of fitted atoms = 0.0014

-3.5692(0.0050)x + 6.8088(0.0093)y + 4.3640(0.0243)z = 2.8396(0.0222)

Angle to previous plane (with approximate e.s.d.) = 1.21 (18)

* -0.0125 (0.0016) N1 * 0.0115 (0.0015) C3 * -0.0058 (0.0015) C4 * -0.0010 (0.0016) C9 * 0.0078 (0.0015) C10 0.0664 (0.0037) O3 1.6122 (0.0047) C1 0.2270 (0.0044) C2

Rms deviation of fitted atoms = 0.0088

2.4277(0.0068)x + 8.5399(0.0077)y + 3.6905(0.0250)z = 6.0406(0.0183)

Angle to previous plane (with approximate e.s.d.) = 71.72 (9)

* 0.0062 (0.0007) O1 * 0.0076 (0.0009) O2 * -0.0191 (0.0022) C1 * 0.0053 (0.0006) C2 - 0.5248 (0.0042) N1 - 2.6141 (0.0031) O3 - 1.7542 (0.0044) C3

Rms deviation of fitted atoms = 0.0111

-3.5683(0.0045)x + 6.8741(0.0085)y + 3.9846(0.0239)z = 2.4843(0.0240)

Angle to previous plane (with approximate e.s.d.) = 71.61 (8)

* 0.0011 (0.0018) C4 * 0.0010 (0.0020) C5 * -0.0020 (0.0022) C6 * 0.0009 (0.0022) C7 * 0.0011 (0.0021) C8 * -0.0021 (0.0019) C9

Rms deviation of fitted atoms = 0.0014

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

	x	y	z	Uiso*/Ueq
O1	0.2219 (4)	0.3422 (2)	0.70076 (9)	0.0436 (5)
O2	0.1185 (4)	0.3225 (2)	0.81453 (9)	0.0448 (6)
O3	0.1743 (4)	0.00701 (19)	0.79755 (9)	0.0431 (5)
N1	0.5015 (4)	0.1415 (2)	0.83717 (10)	0.0322 (5)
C1	0.2613 (6)	0.2997 (3)	0.76625 (14)	0.0319 (6)
C2	0.5186 (5)	0.2258 (3)	0.77452 (12)	0.0336 (6)
C3	0.3211 (5)	0.0455 (2)	0.84486 (13)	0.0322 (6)
C4	0.3303 (5)	0.0001 (2)	0.91926 (13)	0.0330 (6)
C5	0.1849 (6)	−0.0953 (3)	0.95365 (15)	0.0466 (8)
C6	0.2280 (7)	−0.1147 (3)	1.02500 (16)	0.0554 (9)
C7	0.4113 (7)	−0.0391 (3)	1.05950 (15)	0.0572 (9)
C8	0.5580 (6)	0.0569 (3)	1.02528 (15)	0.0508 (9)
C9	0.5160 (5)	0.0761 (3)	0.95383 (13)	0.0367 (6)
C10	0.6353 (5)	0.1726 (3)	0.90280 (13)	0.0405 (7)
C11	0.6091 (6)	0.1497 (3)	0.70982 (14)	0.0442 (8)
H1	0.0983	0.3938	0.7001	0.065*
H2	0.6494	0.2948	0.7844	0.040*
H5	0.0610	−0.1454	0.9296	0.056*
H6	0.1330	−0.1789	1.0497	0.067*
H7	0.4373	−0.0532	1.1076	0.069*
H8	0.6812	0.1072	1.0495	0.061*
H10A	0.6056	0.2653	0.9170	0.049*
H10B	0.8195	0.1572	0.8984	0.049*
H11A	0.7728	0.1082	0.7195	0.066*
H11B	0.6269	0.2112	0.6709	0.066*
H11C	0.4850	0.0814	0.6980	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0367 (11)	0.0525 (12)	0.0415 (11)	0.0129 (11)	−0.0004 (9)	0.0086 (9)
O2	0.0356 (12)	0.0555 (14)	0.0432 (11)	0.0109 (10)	0.0066 (9)	0.0017 (10)
O3	0.0423 (12)	0.0474 (11)	0.0398 (10)	−0.0156 (12)	−0.0101 (10)	0.0011 (9)
N1	0.0268 (11)	0.0351 (11)	0.0346 (12)	−0.0030 (11)	−0.0047 (11)	0.0020 (9)
C1	0.0296 (14)	0.0298 (14)	0.0361 (14)	−0.0031 (12)	−0.0020 (13)	0.0015 (11)
C2	0.0254 (14)	0.0331 (13)	0.0421 (15)	−0.0032 (14)	−0.0012 (14)	0.0010 (12)
C3	0.0313 (15)	0.0297 (14)	0.0355 (13)	0.0004 (12)	−0.0016 (13)	0.0001 (11)
C4	0.0310 (15)	0.0323 (14)	0.0358 (13)	0.0052 (14)	0.0016 (12)	0.0000 (12)
C5	0.0481 (19)	0.0442 (16)	0.0475 (17)	−0.0025 (15)	0.0007 (16)	0.0029 (14)
C6	0.058 (2)	0.062 (2)	0.0467 (17)	0.0016 (19)	0.0083 (18)	0.0145 (15)
C7	0.060 (2)	0.076 (2)	0.0359 (16)	0.014 (2)	0.0000 (16)	0.0101 (15)
C8	0.0430 (19)	0.069 (2)	0.0406 (16)	−0.0017 (17)	−0.0064 (15)	−0.0016 (15)
C9	0.0297 (14)	0.0457 (15)	0.0346 (13)	0.0050 (14)	−0.0017 (13)	−0.0025 (12)
C10	0.0297 (15)	0.0476 (16)	0.0440 (15)	−0.0024 (15)	−0.0065 (13)	−0.0056 (13)
C11	0.0408 (18)	0.0467 (16)	0.0452 (16)	0.0089 (16)	0.0058 (14)	0.0015 (14)

Geometric parameters (Å, º)

O1—C1	1.324 (3)	C8—C9	1.382 (4)
O2—C1	1.197 (3)	C9—C10	1.493 (4)
O3—C3	1.235 (3)	O1—H1	0.82
N1—C2	1.453 (3)	C2—H2	0.98
N1—C3	1.342 (3)	C5—H5	0.93
N1—C10	1.455 (3)	C6—H6	0.93
C1—C2	1.528 (4)	C7—H7	0.93
C2—C11	1.512 (4)	C8—H8	0.93
C3—C4	1.479 (4)	C10—H10A	0.97
C4—C5	1.373 (4)	C10—H10B	0.97
C4—C9	1.385 (4)	C11—H11A	0.96
C5—C6	1.382 (4)	C11—H11B	0.96
C6—C7	1.374 (5)	C11—H11C	0.96
C7—C8	1.380 (4)
C2—N1—C3	122.6 (2)	C1—O1—H1	109.5
C2—N1—C10	123.1 (2)	N1—C2—H2	106.7
C3—N1—C10	112.9 (2)	C11—C2—H2	106.7
O1—C1—O2	123.9 (3)	C1—C2—H2	106.7
O1—C1—C2	112.5 (2)	C4—C5—H5	121.0
O2—C1—C2	123.5 (2)	C6—C5—H5	121.0
N1—C2—C1	107.8 (2)	C7—C6—H6	120.0
N1—C2—C11	113.1 (2)	C5—C6—H6	120.0
C1—C2—C11	115.2 (2)	C6—C7—H7	118.9
O3—C3—N1	124.7 (2)	C8—C7—H7	118.9
O3—C3—C4	128.0 (2)	C7—C8—H8	121.1
N1—C3—C4	107.3 (2)	C9—C8—H8	121.1
C3—C4—C5	130.0 (3)	N1—C10—H10A	111.2
C3—C4—C9	107.9 (2)	C9—C10—H10A	111.2
C5—C4—C9	122.1 (2)	N1—C10—H10B	111.2
C4—C5—C6	118.1 (3)	C9—C10—H10B	111.2
C5—C6—C7	120.0 (3)	H10A—C10—H10B	109.1
C6—C7—C8	122.3 (3)	C2—C11—H11A	109.5
C7—C8—C9	117.8 (3)	C2—C11—H11B	109.5
C4—C9—C8	119.8 (3)	H11A—C11—H11B	109.5
C4—C9—C10	109.3 (2)	C2—C11—H11C	109.5
C8—C9—C10	130.9 (3)	H11A—C11—H11C	109.5
N1—C10—C9	102.7 (2)	H11B—C11—H11C	109.5
C3—N1—C2—C1	58.3 (3)	C9—C4—C5—C6	0.0 (4)
C10—N1—C2—C1	−107.1 (3)	C3—C4—C5—C6	−177.7 (3)
C3—N1—C2—C11	−70.3 (3)	C4—C5—C6—C7	0.3 (4)
C10—N1—C2—C11	124.3 (3)	C5—C6—C7—C8	−0.3 (5)
O2—C1—C2—N1	25.0 (4)	C6—C7—C8—C9	0.0 (5)
O1—C1—C2—N1	−158.7 (2)	C7—C8—C9—C4	0.3 (4)
O2—C1—C2—C11	152.4 (3)	C7—C8—C9—C10	178.2 (3)
O1—C1—C2—C11	−31.3 (3)	C5—C4—C9—C8	−0.3 (4)
C2—N1—C3—O3	9.6 (4)	C3—C4—C9—C8	177.8 (3)
C10—N1—C3—O3	176.3 (2)	C5—C4—C9—C10	−178.6 (2)
C2—N1—C3—C4	−169.1 (2)	C3—C4—C9—C10	−0.5 (3)
C10—N1—C3—C4	−2.3 (3)	C3—N1—C10—C9	2.0 (3)
O3—C3—C4—C5	1.1 (5)	C2—N1—C10—C9	168.6 (2)
N1—C3—C4—C5	179.7 (3)	C8—C9—C10—N1	−178.9 (3)
O3—C3—C4—C9	−176.9 (3)	C4—C9—C10—N1	−0.8 (3)
N1—C3—C4—C9	1.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.82	1.80	2.623 (3)	178
C2—H2···O2^ii	0.98	2.51	3.338 (4)	142
C11—H11C···O3	0.96	2.58	3.135 (4)	117

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