(E)-1-(4-Carboxy­phenyl­methyl­ene)-2-tetralone

The title compound, C₁₈H₁₄O₃, crystallizes in space group P2₁/c as hydrogen-bonded dimers with crystallographic inversion symmetry.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.154
• Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Xtal3.7 (Hall et al., 2000); software used to prepare material for publication: SHELXL97.

(E)-1-(4-carboxyphenylmethylene)-2-tetralone

Crystal data

C18H14O3	F(000) = 584
Mr = 278.29	Dx = 1.368 Mg m^−3
Monoclinic, P21/c	Melting point = 504–506 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.435 (2) Å	Cell parameters from 2457 reflections
b = 14.604 (6) Å	θ = 2.5–25°
c = 16.388 (6) Å	µ = 0.09 mm^−1
β = 118.641 (7)°	T = 193 K
V = 1351.6 (9) Å^3	Fragment, yellow
Z = 4	0.35 × 0.22 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1652 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
Graphite monochromator	θmax = 25.9°, θmin = 2.0°
Detector resolution: 17 pixels mm^-1	h = −7→6
φ and ω scans	k = 0→17
6165 measured reflections	l = 0→20
2571 independent reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0842P)^2] where P = (Fo^2 + 2Fc^2)/3
2571 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.26 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.

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
O1	1.0247 (3)	0.10415 (13)	0.70605 (11)	0.0438 (5)
O2	0.2760 (3)	−0.00542 (12)	0.08218 (11)	0.0399 (5)
O3	−0.0271 (3)	0.05812 (13)	0.09288 (11)	0.0424 (5)
H3	−0.1058	0.0349	0.0398	0.051*
C1	1.1240 (4)	0.14346 (17)	0.66908 (16)	0.0328 (6)
C2	1.0058 (4)	0.15540 (17)	0.56433 (15)	0.0301 (6)
C3	1.1254 (4)	0.21735 (16)	0.52798 (15)	0.0297 (5)
C4	0.9985 (4)	0.26761 (17)	0.44553 (16)	0.0364 (6)
H4	0.8310	0.2622	0.4117	0.044*
C5	1.1129 (5)	0.32479 (18)	0.41275 (18)	0.0431 (7)
H5	1.0248	0.3568	0.3559	0.052*
C6	1.3563 (5)	0.33535 (18)	0.46290 (19)	0.0467 (7)
H6	1.4360	0.3741	0.4403	0.056*
C7	1.4828 (4)	0.28900 (18)	0.54623 (18)	0.0405 (7)
H7	1.6490	0.2980	0.5814	0.049*
C8	1.3720 (4)	0.22964 (17)	0.57947 (16)	0.0332 (6)
C9	1.5075 (4)	0.17926 (18)	0.67052 (17)	0.0399 (6)
H9A	1.6635	0.2088	0.7080	0.048*
H9B	1.5351	0.1152	0.6582	0.048*
C10	1.3706 (4)	0.17984 (17)	0.72471 (16)	0.0362 (6)
H10A	1.4565	0.1423	0.7815	0.043*
H10B	1.3630	0.2433	0.7443	0.043*
C11	0.8013 (4)	0.11099 (17)	0.51606 (16)	0.0327 (6)
H11	0.7428	0.0828	0.5533	0.039*
C12	0.6490 (4)	0.09779 (17)	0.41454 (15)	0.0316 (6)
C13	0.7409 (4)	0.07801 (17)	0.35456 (16)	0.0346 (6)
H13	0.9076	0.0778	0.3780	0.042*
C14	0.5938 (4)	0.05889 (16)	0.26210 (16)	0.0327 (6)
H14	0.6597	0.0445	0.2227	0.039*
C15	0.3494 (4)	0.06056 (15)	0.22597 (15)	0.0286 (5)
C16	0.2543 (4)	0.08143 (17)	0.28451 (16)	0.0333 (6)
H16	0.0875	0.0835	0.2603	0.040*
C17	0.4033 (4)	0.09911 (17)	0.37777 (16)	0.0352 (6)
H17	0.3373	0.1124	0.4174	0.042*
C18	0.1965 (4)	0.03536 (16)	0.12710 (16)	0.0309 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0489 (11)	0.0605 (12)	0.0322 (10)	−0.0019 (9)	0.0277 (9)	−0.0001 (9)
O2	0.0393 (9)	0.0502 (11)	0.0307 (9)	0.0022 (8)	0.0172 (8)	−0.0099 (9)
O3	0.0402 (10)	0.0517 (12)	0.0299 (10)	0.0048 (8)	0.0125 (8)	−0.0103 (9)
C1	0.0402 (13)	0.0364 (14)	0.0281 (13)	0.0034 (11)	0.0215 (11)	−0.0054 (12)
C2	0.0352 (12)	0.0347 (13)	0.0256 (12)	0.0037 (10)	0.0188 (11)	−0.0001 (11)
C3	0.0368 (13)	0.0305 (13)	0.0282 (12)	−0.0012 (10)	0.0208 (11)	−0.0061 (11)
C4	0.0449 (14)	0.0376 (14)	0.0286 (13)	−0.0027 (11)	0.0191 (12)	−0.0028 (12)
C5	0.0651 (18)	0.0381 (15)	0.0330 (14)	−0.0037 (13)	0.0291 (14)	−0.0006 (13)
C6	0.0674 (19)	0.0424 (16)	0.0479 (17)	−0.0122 (14)	0.0417 (15)	−0.0064 (14)
C7	0.0437 (14)	0.0432 (16)	0.0445 (16)	−0.0073 (12)	0.0291 (13)	−0.0092 (14)
C8	0.0395 (13)	0.0337 (13)	0.0336 (13)	−0.0018 (11)	0.0234 (11)	−0.0086 (12)
C9	0.0352 (14)	0.0427 (15)	0.0406 (15)	−0.0018 (11)	0.0171 (12)	−0.0007 (13)
C10	0.0419 (14)	0.0382 (14)	0.0256 (12)	−0.0005 (11)	0.0139 (11)	−0.0045 (12)
C11	0.0379 (12)	0.0401 (14)	0.0274 (12)	−0.0005 (11)	0.0216 (11)	−0.0010 (12)
C12	0.0371 (13)	0.0342 (13)	0.0269 (13)	−0.0055 (10)	0.0181 (11)	−0.0036 (11)
C13	0.0318 (12)	0.0414 (14)	0.0351 (14)	−0.0035 (11)	0.0195 (11)	−0.0059 (12)
C14	0.0388 (13)	0.0354 (14)	0.0301 (13)	−0.0012 (10)	0.0216 (11)	−0.0058 (11)
C15	0.0361 (12)	0.0249 (12)	0.0273 (12)	−0.0035 (10)	0.0173 (11)	−0.0025 (10)
C16	0.0291 (11)	0.0405 (14)	0.0336 (13)	−0.0043 (10)	0.0176 (11)	−0.0019 (12)
C17	0.0396 (13)	0.0426 (15)	0.0329 (14)	−0.0063 (11)	0.0250 (11)	−0.0066 (12)
C18	0.0354 (13)	0.0293 (12)	0.0303 (13)	0.0008 (10)	0.0175 (11)	0.0025 (11)

Geometric parameters (Å, º)

O1—C1	1.215 (3)	C9—C10	1.521 (3)
O2—C18	1.233 (3)	C9—H9A	0.990
O3—C18	1.312 (3)	C9—H9B	0.990
O3—H3	0.840	C10—H10A	0.990
C1—C10	1.498 (3)	C10—H10B	0.990
C1—C2	1.518 (3)	C11—C12	1.484 (3)
C2—C11	1.334 (3)	C11—H11	0.950
C2—C3	1.485 (3)	C12—C17	1.396 (3)
C3—C4	1.405 (3)	C12—C13	1.399 (3)
C3—C8	1.406 (3)	C13—C14	1.377 (3)
C4—C5	1.381 (3)	C13—H13	0.950
C4—H4	0.950	C14—C15	1.390 (3)
C5—C6	1.385 (4)	C14—H14	0.950
C5—H5	0.950	C15—C16	1.397 (3)
C6—C7	1.386 (4)	C15—C18	1.484 (3)
C6—H6	0.950	C16—C17	1.385 (3)
C7—C8	1.389 (3)	C16—H16	0.950
C7—H7	0.950	C17—H17	0.950
C8—C9	1.510 (3)
C18—O3—H3	109.5	C1—C10—C9	112.55 (19)
O1—C1—C10	121.4 (2)	C1—C10—H10A	109.1
O1—C1—C2	121.3 (2)	C9—C10—H10A	109.1
C10—C1—C2	117.3 (2)	C1—C10—H10B	109.1
C11—C2—C3	127.7 (2)	C9—C10—H10B	109.1
C11—C2—C1	115.6 (2)	H10A—C10—H10B	107.8
C3—C2—C1	116.6 (2)	C2—C11—C12	131.4 (2)
C4—C3—C8	118.6 (2)	C2—C11—H11	114.3
C4—C3—C2	122.0 (2)	C12—C11—H11	114.3
C8—C3—C2	119.3 (2)	C17—C12—C13	118.2 (2)
C5—C4—C3	121.2 (2)	C17—C12—C11	119.0 (2)
C5—C4—H4	119.4	C13—C12—C11	122.7 (2)
C3—C4—H4	119.4	C14—C13—C12	121.0 (2)
C4—C5—C6	119.9 (2)	C14—C13—H13	119.5
C4—C5—H5	120.0	C12—C13—H13	119.5
C6—C5—H5	120.0	C13—C14—C15	120.4 (2)
C5—C6—C7	119.6 (2)	C13—C14—H14	119.8
C5—C6—H6	120.2	C15—C14—H14	119.8
C7—C6—H6	120.2	C14—C15—C16	119.4 (2)
C6—C7—C8	121.5 (2)	C14—C15—C18	118.9 (2)
C6—C7—H7	119.3	C16—C15—C18	121.6 (2)
C8—C7—H7	119.3	C17—C16—C15	119.9 (2)
C7—C8—C3	119.2 (2)	C17—C16—H16	120.0
C7—C8—C9	122.0 (2)	C15—C16—H16	120.0
C3—C8—C9	118.8 (2)	C16—C17—C12	121.0 (2)
C8—C9—C10	110.62 (19)	C16—C17—H17	119.5
C8—C9—H9A	109.5	C12—C17—H17	119.5
C10—C9—H9A	109.5	O2—C18—O3	123.5 (2)
C8—C9—H9B	109.5	O2—C18—C15	121.6 (2)
C10—C9—H9B	109.5	O3—C18—C15	114.9 (2)
H9A—C9—H9B	108.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2^i	0.84	1.81	2.643 (2)	170
C5—H5···O1^ii	0.95	2.52	3.321 (3)	142
C11—H11···O1	0.95	2.30	2.735 (3)	107

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