De­hydro­goniothalamin

The title compound, C₁₃H₁₀O₂, has a trans configuration about the C=C double bond of the phenylethyl­ene side chain and the mol­ecule is nearly planar, with a dihedral angle between the pyrone and benzene rings of 8.54 (6)°. The crystal packing is stabilized by intermolecular C—H...O interactions, which form one-dimensional zigzag chains parallel to [100].

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.126
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Dehydrogoniothalamin

Crystal data

C13H10O2	Dx = 1.299 Mg m^−3
Mr = 198.21	Melting point = 115–116 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 10.0406 (15) Å	Cell parameters from 3875 reflections
b = 13.420 (2) Å	θ = 2.7–27.5°
c = 15.040 (2) Å	µ = 0.09 mm^−1
V = 2026.5 (5) Å^3	T = 273 K
Z = 8	Block, colourless
F(000) = 832	0.50 × 0.46 × 0.43 mm

Data collection

Bruker SMART APEX area-detector diffractometer	2304 independent reflections
Radiation source: fine-focus sealed tube	1819 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 83.66 pixels mm^-1	θmax = 27.5°, θmin = 2.7°
ω scan	h = −12→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→16
Tmin = 0.957, Tmax = 0.963	l = −19→17
11115 measured 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0605P)^2 + 0.3022P] where P = (Fo^2 + 2Fc^2)/3
2304 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.14650 (9)	0.82654 (6)	0.08561 (7)	0.0551 (3)
O2	0.18276 (12)	0.67893 (8)	0.02690 (10)	0.0889 (4)
C2	0.23305 (14)	0.75046 (10)	0.06129 (10)	0.0588 (4)
C3	0.37053 (14)	0.76655 (11)	0.08026 (10)	0.0605 (4)
H3A	0.4328	0.7187	0.0637	0.073*
C4	0.41131 (14)	0.84918 (12)	0.12147 (10)	0.0641 (4)
H4A	0.5012	0.8578	0.1342	0.077*
C5	0.31883 (14)	0.92371 (11)	0.14596 (10)	0.0603 (4)
H5A	0.3475	0.9808	0.1753	0.072*
C6	0.18918 (13)	0.91148 (9)	0.12661 (8)	0.0505 (3)
C7	0.08523 (14)	0.98275 (10)	0.14486 (9)	0.0547 (3)
H7A	0.1085	1.0396	0.1767	0.066*
C8	−0.04138 (14)	0.97384 (9)	0.11986 (9)	0.0526 (3)
H8A	−0.0641	0.9157	0.0898	0.063*
C9	−0.14868 (12)	1.04589 (9)	0.13466 (8)	0.0488 (3)
C10	−0.27362 (14)	1.02825 (11)	0.09762 (9)	0.0593 (4)
H10A	−0.2883	0.9699	0.0657	0.071*
C11	−0.37574 (15)	1.09593 (13)	0.10764 (11)	0.0679 (4)
H11A	−0.4586	1.0830	0.0825	0.082*
C12	−0.35577 (15)	1.18240 (11)	0.15454 (11)	0.0682 (4)
H12A	−0.4244	1.2284	0.1606	0.082*
C13	−0.23345 (16)	1.20048 (11)	0.19260 (10)	0.0657 (4)
H13A	−0.2199	1.2587	0.2249	0.079*
C14	−0.13079 (14)	1.13306 (10)	0.18333 (9)	0.0563 (3)
H14A	−0.0489	1.1460	0.2098	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0468 (5)	0.0461 (5)	0.0724 (6)	−0.0002 (4)	0.0020 (4)	−0.0084 (4)
O2	0.0710 (7)	0.0618 (7)	0.1339 (11)	0.0017 (5)	−0.0016 (7)	−0.0350 (7)
C2	0.0558 (8)	0.0500 (7)	0.0705 (9)	0.0035 (6)	0.0047 (6)	−0.0043 (6)
C3	0.0521 (7)	0.0608 (8)	0.0686 (8)	0.0097 (6)	0.0050 (6)	0.0015 (7)
C4	0.0459 (7)	0.0732 (9)	0.0732 (9)	−0.0012 (7)	−0.0025 (6)	0.0045 (8)
C5	0.0566 (8)	0.0570 (8)	0.0673 (8)	−0.0073 (6)	−0.0041 (6)	−0.0055 (7)
C6	0.0534 (7)	0.0447 (7)	0.0534 (7)	−0.0027 (6)	0.0013 (6)	−0.0001 (5)
C7	0.0594 (8)	0.0455 (7)	0.0592 (7)	−0.0007 (6)	0.0024 (6)	−0.0052 (6)
C8	0.0592 (8)	0.0429 (7)	0.0557 (7)	−0.0015 (6)	0.0033 (6)	−0.0030 (5)
C9	0.0524 (7)	0.0450 (7)	0.0491 (7)	−0.0012 (5)	0.0048 (5)	0.0029 (5)
C10	0.0584 (8)	0.0564 (8)	0.0631 (8)	−0.0044 (6)	−0.0002 (6)	−0.0008 (6)
C11	0.0522 (8)	0.0768 (10)	0.0748 (9)	0.0006 (7)	0.0020 (7)	0.0143 (8)
C12	0.0635 (9)	0.0642 (9)	0.0769 (10)	0.0154 (7)	0.0199 (7)	0.0156 (8)
C13	0.0768 (10)	0.0516 (8)	0.0688 (9)	0.0047 (7)	0.0168 (7)	−0.0044 (6)
C14	0.0580 (8)	0.0523 (8)	0.0585 (7)	−0.0006 (6)	0.0032 (6)	−0.0046 (6)

Geometric parameters (Å, º)

O1—C6	1.3650 (15)	C8—C9	1.4645 (18)
O1—C2	1.3897 (16)	C8—H8A	0.9300
O2—C2	1.2016 (17)	C9—C14	1.3916 (18)
C2—C3	1.426 (2)	C9—C10	1.3928 (19)
C3—C4	1.335 (2)	C10—C11	1.378 (2)
C3—H3A	0.9300	C10—H10A	0.9300
C4—C5	1.414 (2)	C11—C12	1.373 (2)
C4—H4A	0.9300	C11—H11A	0.9300
C5—C6	1.3440 (19)	C12—C13	1.376 (2)
C5—H5A	0.9300	C12—H12A	0.9300
C6—C7	1.4421 (18)	C13—C14	1.379 (2)
C7—C8	1.3311 (19)	C13—H13A	0.9300
C7—H7A	0.9300	C14—H14A	0.9300
C6—O1—C2	122.42 (11)	C7—C8—H8A	116.6
O2—C2—O1	115.94 (13)	C9—C8—H8A	116.6
O2—C2—C3	127.87 (14)	C14—C9—C10	118.00 (12)
O1—C2—C3	116.19 (12)	C14—C9—C8	122.68 (12)
C4—C3—C2	121.04 (13)	C10—C9—C8	119.31 (12)
C4—C3—H3A	119.5	C11—C10—C9	120.96 (14)
C2—C3—H3A	119.5	C11—C10—H10A	119.5
C3—C4—C5	120.48 (13)	C9—C10—H10A	119.5
C3—C4—H4A	119.8	C12—C11—C10	120.31 (14)
C5—C4—H4A	119.8	C12—C11—H11A	119.8
C6—C5—C4	119.56 (13)	C10—C11—H11A	119.8
C6—C5—H5A	120.2	C11—C12—C13	119.54 (14)
C4—C5—H5A	120.2	C11—C12—H12A	120.2
C5—C6—O1	120.26 (12)	C13—C12—H12A	120.2
C5—C6—C7	125.36 (13)	C12—C13—C14	120.62 (14)
O1—C6—C7	114.37 (11)	C12—C13—H13A	119.7
C8—C7—C6	125.30 (12)	C14—C13—H13A	119.7
C8—C7—H7A	117.4	C13—C14—C9	120.56 (14)
C6—C7—H7A	117.4	C13—C14—H14A	119.7
C7—C8—C9	126.89 (12)	C9—C14—H14A	119.7
C6—O1—C2—O2	178.88 (13)	C6—C7—C8—C9	−177.93 (12)
C6—O1—C2—C3	−0.99 (19)	C7—C8—C9—C14	−4.0 (2)
O2—C2—C3—C4	−177.94 (16)	C7—C8—C9—C10	174.82 (13)
O1—C2—C3—C4	1.9 (2)	C14—C9—C10—C11	1.1 (2)
C2—C3—C4—C5	−1.1 (2)	C8—C9—C10—C11	−177.84 (12)
C3—C4—C5—C6	−0.7 (2)	C9—C10—C11—C12	0.0 (2)
C4—C5—C6—O1	1.7 (2)	C10—C11—C12—C13	−0.9 (2)
C4—C5—C6—C7	−177.73 (13)	C11—C12—C13—C14	0.6 (2)
C2—O1—C6—C5	−0.77 (19)	C12—C13—C14—C9	0.6 (2)
C2—O1—C6—C7	178.68 (11)	C10—C9—C14—C13	−1.37 (19)
C5—C6—C7—C8	174.75 (14)	C8—C9—C14—C13	177.50 (12)
O1—C6—C7—C8	−4.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1	0.93	2.43	2.7806 (16)	102
C10—H10A···O2^i	0.93	2.45	3.381 (2)	176

Symmetry code: (i) x−1/2, −y+3/2, −z.