2-(3-Oxocyclo­hex-1-en­yl)benzoic acid

Vieira, F.T.; Menezes, D.C.; Lima, G.M. de; Speziali, N.L.

doi:10.1107/S1600536807029959

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2-(3-Oxocyclohex-1-enyl)benzoic acid

F. T. Vieira, D. C. Menezes, G. M. de Lima and N. L. Speziali

The title compound, C₁₃H₁₃NO₃, crystallizes with two molecules in the asymmetric unit. The values of the relevant C—C, C=C and C—N bond lengths indicate that the molecules exist in the enamine tautomeric form. In each molecule, the cyclohexene ring adopts a slightly distorted envelope conformation. Molecules are linked by intermolecular O—H

O hydrogen bonds between carboxyl and C=O groups. There is also an intramolecular N—H

O hydrogen bond in each molecule.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029959/wn2148sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029959/wn2148Isup2.hkl Contains datablock I

CCDC reference: 657665

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.046
wR factor = 0.132
Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated .          !

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.38
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C13'
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5

Alert level G
REFLT03_ALERT_4_G  ALERT: MoKa measured Friedel data cannot be used to
                   determine absolute structure in a light-atom
                   study EXCEPT under VERY special conditions.
                   It is preferred that Friedel data is merged in such cases.
           From the CIF: _diffrn_reflns_theta_max           25.50
           From the CIF: _reflns_number_total               2266
           Count of symmetry unique reflns         2205
           Completeness (_total/calc)            102.77%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured        61
           Fraction of Friedel pairs measured     0.028
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The preparation of the title compound has been reported in the literature in a condensation reaction with isopropylidene malonate (Strozhev & Lielbriedis, 1990). The compound was obtained in 37% yield and no X-ray crystallographic determination has hitherto been performed. A search of the Cambridge Structural Database (Version 5.28; Allen, 2002) yielded no hits.

The title compound crystallizes with two molecules per asymmetric unit. In each molecule the cyclohexene ring adopts a slightly distorted envelope conformation, with C9 and C9' as flap atoms. The bond distances C1—N, N—C7, C7═C12, C12—C11, C1'—N,' N'—C7', C7'═C12' and C12'—C11' (Table 1 and Fig. 1) clearly indicate that the enamine tautomer is present in the crystal structure, rather than the imine normally expected from a Schiff base reaction. The C—N—C bond angles, 131.6 (3)° and 130.7 (3)°, are typical of Nsp³.

The X-ray crystallographic determination has revealed that the title compound exists in the solid state in a pseudo-polymeric arrangement, held together by intermolecular O—H···O hydrogen bonds. These connect carboxyl and C═O groups of neighbouring molecules.

Related literature top

For related literature, see: Allen (2002); Strozhev & Lielbriedis (1990).

Experimental top

To a round-bottomed flask charged with 2-aminobenzoic acid (2.74 g, 0.02 mol) dissolved in methanol (20 ml) was slowly added a solution of 1,3-cyclohexadione (2.24 g, 0.02 mol) in 20 ml of methanol. The mixture was refluxed and stirred for 4 h; it was observed that the colour changed from colourless to yellow. The solution was cooled to room temperature and the solvent was removed in vacuum; the yellow solid was washed with diethyl ether. X-ray quality crystals were obtained after slow evaporation of a methanol/water (9:1) solution. Yield 75%. IR (ν/cm^-1): 1376 (ν_C—N). ¹H-NMR: (δ): 7.97–7.92 d (C3), 7.4 m (C5, C6), 7.09 t (C4), 2.51–2.48 m (C11), 2.26–2.27 m (C9), 1.95–1.92 m (C10). ¹³C-NMR (δ): 201. 9 (C12), 170.4 (C1), 165.4 (C8), 141.9 (C7), 134.6 (C3), 133.6 (C5), 125.5 (C6), 124.64 (C4), 122.58 (C2), 100.94 (C13), 37.12 (C11), 31.07 (C9), 22.92 (C10). Elemental analysis(%) for C₁₃H₁₃NO₃ found (calc.): C 67.21 (67.52), H 5.43 (5.66), N 5.96 (6.05).

Structure description top

For related literature, see: Allen (2002); Strozhev & Lielbriedis (1990).

Computing details top

Data collection: XSCANS (Siemens, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme and the intermolecular hydrogen bond (dashed line) Displacement ellipsoids are drawn at the 50% probability level.

2-(3-Oxocyclohex-1-enyl)benzoic acid top

Crystal data top

C₁₃H₁₃NO₃	D_x = 1.345 Mg m⁻³
M_r = 231.24	Melting point = 183.7–185.5 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
a = 11.3867 (11) Å	Cell parameters from 38 reflections
b = 13.0719 (9) Å	θ = 4.8–12.5°
c = 15.3389 (14) Å	µ = 0.10 mm⁻¹
V = 2283.2 (3) Å³	T = 293 K
Z = 8	Prismatic, colorless
F(000) = 976	0.2 × 0.2 × 0.2 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.015
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 2.1°
Graphite monochromator	h = −1→13
ω / 2θ scans	k = −3→15
2549 measured reflections	l = −4→18
2266 independent reflections	3 standard reflections every 247 reflections
1800 reflections with I > 2σ(I)	intensity decay: 4%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2266 reflections	(Δ/σ)_max = 0.018
307 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₃H₁₃NO₃	V = 2283.2 (3) Å³
M_r = 231.24	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 11.3867 (11) Å	µ = 0.10 mm⁻¹
b = 13.0719 (9) Å	T = 293 K
c = 15.3389 (14) Å	0.2 × 0.2 × 0.2 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.015
2549 measured reflections	3 standard reflections every 247 reflections
2266 independent reflections	intensity decay: 4%
1800 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.132	H-atom parameters constrained
S = 0.93	Δρ_max = 0.18 e Å⁻³
2266 reflections	Δρ_min = −0.25 e Å⁻³
307 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.5835 (3)	0.4550 (2)	0.7105 (2)	0.0678 (9)
O2	0.4210 (2)	0.4172 (2)	0.7836 (2)	0.0644 (9)
H2O	0.4113	0.4792	0.7804	0.097*
C13	0.5183 (3)	0.3924 (3)	0.7441 (3)	0.0452 (9)
C6	0.5421 (3)	0.2797 (3)	0.7469 (2)	0.0402 (8)
C5	0.4676 (3)	0.2177 (3)	0.7959 (3)	0.0465 (9)
H5	0.4034	0.2471	0.8238	0.056*
C4	0.4865 (3)	0.1147 (3)	0.8043 (3)	0.0502 (10)
H4	0.4359	0.0743	0.8373	0.060*
C3	0.5822 (3)	0.0721 (3)	0.7627 (3)	0.0499 (10)
H3	0.5964	0.0024	0.7688	0.060*
C2	0.6568 (3)	0.1297 (3)	0.7128 (2)	0.0426 (8)
H2	0.7204	0.0990	0.6852	0.051*
C1	0.6372 (3)	0.2350 (3)	0.7033 (2)	0.0376 (8)
N	0.7126 (3)	0.2982 (2)	0.6544 (2)	0.0455 (8)
H1	0.7075	0.3621	0.6671	0.055*
C7	0.7918 (3)	0.2764 (3)	0.5909 (2)	0.0403 (8)
C8	0.8719 (3)	0.3646 (3)	0.5703 (3)	0.0443 (9)
H8A	0.9332	0.3678	0.6142	0.053*
H8B	0.8273	0.4277	0.5736	0.053*
C9	0.9286 (4)	0.3574 (3)	0.4812 (3)	0.0530 (11)
H9A	0.9899	0.4086	0.4760	0.064*
H9B	0.8704	0.3704	0.4364	0.064*
C10	0.9808 (4)	0.2511 (3)	0.4687 (3)	0.0519 (11)
H10A	1.0105	0.2450	0.4096	0.062*
H10B	1.0464	0.2424	0.5083	0.062*
C11	0.8926 (3)	0.1686 (3)	0.4848 (3)	0.0394 (8)
C12	0.8009 (3)	0.1860 (3)	0.5470 (3)	0.0400 (8)
H12	0.7463	0.1346	0.5577	0.048*
O3	0.9019 (2)	0.08747 (19)	0.4442 (2)	0.0554 (7)
O1'	0.6639 (3)	0.9504 (2)	0.5383 (2)	0.0723 (10)
O2'	0.8124 (2)	0.9080 (2)	0.4533 (2)	0.0649 (9)
H2O'	0.8278	0.9690	0.4585	0.097*
C13'	0.7225 (3)	0.8857 (3)	0.5014 (3)	0.0429 (9)
C6'	0.6979 (3)	0.7738 (3)	0.5042 (2)	0.0382 (8)
C5'	0.7693 (3)	0.7071 (3)	0.4574 (2)	0.0453 (9)
H5'	0.8350	0.7327	0.4288	0.054*
C4'	0.7451 (3)	0.6040 (3)	0.4525 (3)	0.0484 (9)
H4'	0.7951	0.5602	0.4223	0.058*
C3'	0.6461 (4)	0.5666 (3)	0.4926 (3)	0.0505 (10)
H3'	0.6276	0.4976	0.4874	0.061*
C2'	0.5738 (3)	0.6299 (3)	0.5405 (3)	0.0483 (10)
H2'	0.5075	0.6029	0.5675	0.058*
C1'	0.5988 (3)	0.7339 (3)	0.5491 (3)	0.0393 (8)
N'	0.5268 (2)	0.8004 (2)	0.5962 (2)	0.0455 (8)
H1'	0.5340	0.8638	0.5824	0.055*
C7'	0.4468 (3)	0.7814 (3)	0.6606 (2)	0.0382 (8)
C8'	0.3695 (3)	0.8713 (3)	0.6803 (3)	0.0442 (9)
H8'A	0.3073	0.8746	0.6372	0.053*
H8'B	0.4155	0.9336	0.6755	0.053*
C9'	0.3153 (4)	0.8663 (3)	0.7703 (3)	0.0522 (10)
H9'A	0.2570	0.9199	0.7766	0.063*
H9'B	0.3754	0.8766	0.8142	0.063*
C10'	0.2581 (3)	0.7627 (3)	0.7830 (3)	0.0554 (12)
H10C	0.2285	0.7577	0.8421	0.066*
H10D	0.1918	0.7566	0.7436	0.066*
C11'	0.3422 (3)	0.6767 (3)	0.7664 (2)	0.0408 (8)
C12'	0.4342 (3)	0.6921 (3)	0.7048 (3)	0.0414 (8)
H12'	0.4872	0.6393	0.6946	0.050*
O3'	0.3271 (2)	0.5937 (2)	0.8042 (2)	0.0561 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0716 (18)	0.0402 (15)	0.092 (2)	0.0011 (13)	0.0372 (18)	0.0043 (16)
O2	0.0588 (17)	0.0435 (16)	0.091 (2)	0.0050 (13)	0.0285 (17)	−0.0018 (16)
C13	0.0461 (19)	0.045 (2)	0.045 (2)	0.0024 (17)	0.0071 (18)	−0.0055 (18)
C6	0.0461 (19)	0.0359 (18)	0.038 (2)	−0.0023 (17)	−0.0044 (17)	−0.0062 (17)
C5	0.049 (2)	0.041 (2)	0.049 (2)	−0.0028 (17)	0.0085 (19)	0.0007 (18)
C4	0.060 (2)	0.044 (2)	0.046 (2)	−0.0035 (18)	0.008 (2)	0.0064 (18)
C3	0.063 (2)	0.0385 (19)	0.048 (2)	0.0012 (17)	−0.007 (2)	0.0031 (18)
C2	0.0444 (19)	0.0402 (19)	0.043 (2)	0.0068 (15)	−0.0017 (17)	−0.0013 (17)
C1	0.0384 (17)	0.0371 (17)	0.037 (2)	−0.0025 (14)	−0.0024 (17)	−0.0030 (16)
N	0.0464 (17)	0.0346 (15)	0.0555 (19)	−0.0008 (13)	0.0066 (15)	−0.0099 (15)
C7	0.0339 (17)	0.0378 (17)	0.049 (2)	−0.0029 (14)	−0.0030 (16)	−0.0041 (18)
C8	0.0448 (19)	0.0363 (18)	0.052 (2)	−0.0058 (15)	−0.0018 (17)	−0.0042 (17)
C9	0.065 (2)	0.042 (2)	0.052 (3)	−0.0191 (19)	0.008 (2)	−0.0043 (19)
C10	0.049 (2)	0.047 (2)	0.059 (3)	−0.0076 (18)	0.015 (2)	−0.0035 (19)
C11	0.0401 (17)	0.0319 (18)	0.046 (2)	−0.0004 (14)	0.0026 (16)	0.0001 (16)
C12	0.0359 (16)	0.0380 (17)	0.046 (2)	−0.0066 (14)	0.0041 (17)	0.0014 (17)
O3	0.0650 (17)	0.0355 (14)	0.0656 (18)	0.0000 (12)	0.0215 (15)	−0.0052 (14)
O1'	0.0770 (19)	0.0384 (15)	0.101 (3)	−0.0051 (14)	0.037 (2)	−0.0025 (17)
O2'	0.0670 (18)	0.0403 (15)	0.087 (2)	−0.0120 (13)	0.0299 (18)	−0.0014 (15)
C13'	0.0424 (19)	0.041 (2)	0.045 (2)	0.0014 (16)	0.0018 (18)	0.0038 (17)
C6'	0.0377 (17)	0.0398 (18)	0.037 (2)	0.0003 (15)	−0.0006 (16)	0.0032 (17)
C5'	0.049 (2)	0.048 (2)	0.038 (2)	−0.0001 (17)	0.0035 (18)	0.0046 (17)
C4'	0.063 (2)	0.0412 (18)	0.041 (2)	0.0035 (17)	0.004 (2)	−0.0007 (17)
C3'	0.066 (2)	0.0405 (19)	0.045 (2)	−0.0042 (17)	−0.001 (2)	−0.0029 (18)
C2'	0.046 (2)	0.049 (2)	0.050 (2)	−0.0092 (16)	0.0038 (18)	0.001 (2)
C1'	0.0395 (17)	0.0369 (17)	0.041 (2)	−0.0013 (14)	−0.0009 (18)	0.0038 (17)
N'	0.0452 (16)	0.0347 (15)	0.057 (2)	0.0013 (13)	0.0130 (16)	0.0070 (14)
C7'	0.0365 (17)	0.0368 (18)	0.041 (2)	−0.0046 (15)	−0.0048 (16)	−0.0014 (17)
C8'	0.0465 (19)	0.0352 (18)	0.051 (2)	0.0062 (15)	−0.0039 (17)	0.0052 (17)
C9'	0.063 (2)	0.036 (2)	0.058 (3)	0.0126 (18)	0.008 (2)	0.0006 (19)
C10'	0.051 (2)	0.048 (2)	0.067 (3)	0.0101 (18)	0.020 (2)	0.003 (2)
C11'	0.0426 (19)	0.0365 (19)	0.043 (2)	−0.0018 (15)	−0.0009 (17)	0.0003 (17)
C12'	0.0393 (17)	0.0324 (17)	0.053 (2)	0.0041 (14)	0.0028 (18)	0.0022 (17)
O3'	0.0614 (17)	0.0407 (15)	0.0662 (19)	0.0029 (12)	0.0232 (16)	0.0095 (13)

Geometric parameters (Å, º) top

O1—C13	1.219 (5)	O1'—C13'	1.216 (4)
O2—C13	1.304 (4)	O2'—C13'	1.295 (4)
O2—H2O	0.8200	O2'—H2O'	0.8200
C13—C6	1.498 (5)	C13'—C6'	1.490 (5)
C6—C5	1.393 (5)	C6'—C5'	1.392 (5)
C6—C1	1.401 (5)	C6'—C1'	1.421 (5)
C5—C4	1.370 (6)	C5'—C4'	1.378 (5)
C5—H5	0.9300	C5'—H5'	0.9300
C4—C3	1.379 (6)	C4'—C3'	1.374 (6)
C4—H4	0.9300	C4'—H4'	0.9300
C3—C2	1.370 (5)	C3'—C2'	1.380 (6)
C3—H3	0.9300	C3'—H3'	0.9300
C2—C1	1.402 (5)	C2'—C1'	1.395 (5)
C2—H2	0.9300	C2'—H2'	0.9300
C1—N	1.407 (5)	C1'—N'	1.396 (5)
N—C7	1.359 (5)	N'—C7'	1.366 (5)
N—H1	0.8600	N'—H1'	0.8600
C7—C12	1.364 (5)	C7'—C12'	1.358 (5)
C7—C8	1.504 (5)	C7'—C8'	1.500 (5)
C8—C9	1.514 (6)	C8'—C9'	1.513 (6)
C8—H8A	0.9700	C8'—H8'A	0.9700
C8—H8B	0.9700	C8'—H8'B	0.9700
C9—C10	1.524 (6)	C9'—C10'	1.515 (5)
C9—H9A	0.9700	C9'—H9'A	0.9700
C9—H9B	0.9700	C9'—H9'B	0.9700
C10—C11	1.494 (5)	C10'—C11'	1.499 (5)
C10—H10A	0.9700	C10'—H10C	0.9700
C10—H10B	0.9700	C10'—H10D	0.9700
C11—O3	1.234 (4)	C11'—O3'	1.242 (4)
C11—C12	1.433 (5)	C11'—C12'	1.425 (5)
C12—H12	0.9300	C12'—H12'	0.9300

C13—O2—H2O	109.5	C13'—O2'—H2O'	109.5
O1—C13—O2	123.1 (4)	O1'—C13'—O2'	122.8 (3)
O1—C13—C6	124.3 (4)	O1'—C13'—C6'	124.5 (3)
O2—C13—C6	112.6 (3)	O2'—C13'—C6'	112.7 (3)
C5—C6—C1	119.0 (4)	C5'—C6'—C1'	119.0 (3)
C5—C6—C13	118.5 (3)	C5'—C6'—C13'	119.4 (3)
C1—C6—C13	122.4 (3)	C1'—C6'—C13'	121.6 (3)
C4—C5—C6	121.8 (4)	C4'—C5'—C6'	121.6 (4)
C4—C5—H5	119.1	C4'—C5'—H5'	119.2
C6—C5—H5	119.1	C6'—C5'—H5'	119.2
C5—C4—C3	118.5 (4)	C3'—C4'—C5'	119.1 (4)
C5—C4—H4	120.8	C3'—C4'—H4'	120.4
C3—C4—H4	120.8	C5'—C4'—H4'	120.4
C2—C3—C4	121.8 (4)	C4'—C3'—C2'	121.0 (4)
C2—C3—H3	119.1	C4'—C3'—H3'	119.5
C4—C3—H3	119.1	C2'—C3'—H3'	119.5
C3—C2—C1	119.9 (4)	C3'—C2'—C1'	120.8 (4)
C3—C2—H2	120.0	C3'—C2'—H2'	119.6
C1—C2—H2	120.0	C1'—C2'—H2'	119.6
C6—C1—C2	118.9 (4)	C2'—C1'—N'	122.4 (3)
C6—C1—N	118.7 (3)	C2'—C1'—C6'	118.3 (3)
C2—C1—N	122.3 (3)	N'—C1'—C6'	119.2 (3)
C7—N—C1	131.6 (3)	C7'—N'—C1'	130.7 (3)
C7—N—H1	114.2	C7'—N'—H1'	114.6
C1—N—H1	114.2	C1'—N'—H1'	114.6
N—C7—C12	125.9 (3)	C12'—C7'—N'	126.0 (3)
N—C7—C8	113.2 (3)	C12'—C7'—C8'	120.7 (3)
C12—C7—C8	121.0 (3)	N'—C7'—C8'	113.3 (3)
C7—C8—C9	113.6 (3)	C7'—C8'—C9'	112.9 (3)
C7—C8—H8A	108.8	C7'—C8'—H8'A	109.0
C9—C8—H8A	108.8	C9'—C8'—H8'A	109.0
C7—C8—H8B	108.8	C7'—C8'—H8'B	109.0
C9—C8—H8B	108.8	C9'—C8'—H8'B	109.0
H8A—C8—H8B	107.7	H8'A—C8'—H8'B	107.8
C8—C9—C10	109.7 (4)	C8'—C9'—C10'	109.3 (4)
C8—C9—H9A	109.7	C8'—C9'—H9'A	109.8
C10—C9—H9A	109.7	C10'—C9'—H9'A	109.8
C8—C9—H9B	109.7	C8'—C9'—H9'B	109.8
C10—C9—H9B	109.7	C10'—C9'—H9'B	109.8
H9A—C9—H9B	108.2	H9'A—C9'—H9'B	108.3
C11—C10—C9	112.0 (3)	C11'—C10'—C9'	112.0 (3)
C11—C10—H10A	109.2	C11'—C10'—H10C	109.2
C9—C10—H10A	109.2	C9'—C10'—H10C	109.2
C11—C10—H10B	109.2	C11'—C10'—H10D	109.2
C9—C10—H10B	109.2	C9'—C10'—H10D	109.2
H10A—C10—H10B	107.9	H10C—C10'—H10D	107.9
O3—C11—C12	122.3 (3)	O3'—C11'—C12'	122.3 (3)
O3—C11—C10	118.6 (3)	O3'—C11'—C10'	119.2 (3)
C12—C11—C10	119.0 (3)	C12'—C11'—C10'	118.4 (3)
C7—C12—C11	121.4 (3)	C7'—C12'—C11'	122.0 (3)
C7—C12—H12	119.3	C7'—C12'—H12'	119.0
C11—C12—H12	119.3	C11'—C12'—H12'	119.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3′	0.82	1.81	2.562 (4)	151
N—H1···O1	0.86	1.98	2.665 (4)	136
O2′—H2O′···O3ⁱ	0.82	1.78	2.562 (4)	160
N′—H1′···O1′	0.86	1.98	2.659 (4)	135

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO₃
M_r	231.24
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	11.3867 (11), 13.0719 (9), 15.3389 (14)
V (Å³)	2283.2 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Siemens P4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2549, 2266, 1800
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 0.93
No. of reflections	2266
No. of parameters	307
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.25

Computer programs: XSCANS (Siemens, 1991), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), SHELXL97.

Selected bond lengths (Å) top

C1—N	1.407 (5)	C1'—N'	1.396 (5)
N—C7	1.359 (5)	N'—C7'	1.366 (5)
C7—C12	1.364 (5)	C7'—C12'	1.358 (5)
C11—C12	1.433 (5)	C11'—C12'	1.425 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3'	0.82	1.81	2.562 (4)	151.1
N—H1···O1	0.86	1.98	2.665 (4)	136.1
O2'—H2O'···O3ⁱ	0.82	1.78	2.562 (4)	159.6
N'—H1'···O1'	0.86	1.98	2.659 (4)	134.9

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

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