5-Acetyl­goniothalamin

In the title compound, C₁₃H₁₀O₂, the pyrone ring adopts a modified screw-boat conformation and a trans configuration about the C=C double bond. The styryl fragment is pseudo-equatorial on the pyrone ring. The mol­ecules are stabilized by inter­molecular C—H...O inter­actions and form a one-dimensional zigzag chain parallel to [100].

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.106
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.82 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               1551
           Count of symmetry unique reflns         1552
           Completeness (_total/calc)             99.94%
           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

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

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

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

5-Acetylgoniothalamin

Crystal data

C15H14O4	F(000) = 544
Mr = 258.26	Dx = 1.286 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1992 reflections
a = 5.3798 (12) Å	θ = 1.8–26.0°
b = 13.659 (3) Å	µ = 0.09 mm^−1
c = 18.153 (4) Å	T = 298 K
V = 1333.9 (5) Å^3	Block, colourless
Z = 4	0.49 × 0.33 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1551 independent reflections
Radiation source: fine-focus sealed tube	1234 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 83.66 pixels mm^-1	θmax = 26.0°, θmin = 1.8°
ω scans	h = −5→6
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −16→16
Tmin = 0.955, Tmax = 0.983	l = −17→22
7462 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0402P)^2 + 0.207P] where P = (Fo^2 + 2Fc^2)/3
1551 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.12 e Å^−3
2 restraints	Δρmin = −0.12 e Å^−3

Special details

Experimental. IR (ν_max, cm^-1): 1740, 1654, 1578, 1493, 1227 and 953; ¹H NMR (CDCl_3, δ, p.m.m.): 7.26 (m, 5H, aromatic), 6.90 (dd, J=10 and 5,H-4), 6.80 (dd, J=15 and 1,H-8), 6.20 (dd, J=10, and 2, H-3), 6.16 (dd, J=15 and 6, H-7), 5.26 (dd, J=6 and 3, H-6), 5.15 (dd, J=5 and 3, H-5) and 2.02 (s, 3H,-OMe). ¹³C NMR (CDCl₃, δ, p.m.m.): 170.2 (s, ester carbonyl), 162.6 (s, C-2), 140.8 (d, C-4), 135.7 (d, C-9), 135.0 (d, C-7), 128.8 (d, C-11 dan C-13), 128.7 (d, C-12), 126.9 (d, C-10 and C-14), 125.0 (d, C-8), 121.2 (d, C-3), 79.2 (d, C-6), 64.0 (d, C-5) and 20.7 (q, Ac).

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.1988 (5)	0.06094 (15)	0.80970 (11)	0.0840 (7)
O2	0.1372 (8)	−0.09214 (18)	0.77891 (15)	0.1312 (13)
O3	0.2487 (4)	0.18972 (13)	0.68682 (11)	0.0684 (6)
O4A	0.469 (2)	0.3000 (15)	0.6310 (14)	0.193 (9)	0.49 (2)
O4B	0.4908 (12)	0.2341 (10)	0.5991 (3)	0.097 (4)	0.51 (2)
C2	0.2664 (10)	−0.0208 (3)	0.77337 (19)	0.0940 (12)
C3	0.4868 (9)	−0.0148 (3)	0.72586 (19)	0.0926 (12)
H3A	0.5674	−0.0721	0.7118	0.111*
C4	0.5721 (8)	0.0695 (3)	0.70293 (18)	0.0838 (10)
H4A	0.7017	0.0717	0.6690	0.101*
C5	0.4615 (6)	0.1620 (2)	0.73118 (15)	0.0650 (8)
H5A	0.5858	0.2144	0.7311	0.078*
C6	0.3681 (7)	0.14439 (19)	0.80823 (16)	0.0680 (8)
H6A	0.5114	0.1287	0.8394	0.082*
C7	0.2879 (6)	0.2407 (3)	0.62717 (18)	0.0792 (10)
C8	0.0637 (7)	0.2650 (2)	0.58597 (16)	0.0774 (9)
H8A	−0.0374	0.2075	0.5807	0.116*
H8B	0.1088	0.2891	0.5381	0.116*
H8C	−0.0280	0.3145	0.6120	0.116*
C9	0.2354 (7)	0.2285 (2)	0.84183 (15)	0.0689 (8)
H9A	0.0928	0.2520	0.8189	0.083*
C10	0.3111 (7)	0.2710 (2)	0.90264 (15)	0.0667 (8)
H10A	0.4515	0.2439	0.9244	0.080*
C11	0.2038 (6)	0.3555 (2)	0.94070 (14)	0.0617 (7)
C12	0.3175 (7)	0.3910 (2)	1.00413 (16)	0.0728 (9)
H12A	0.4606	0.3605	1.0215	0.087*
C13	0.2237 (8)	0.4699 (2)	1.04180 (17)	0.0823 (10)
H13A	0.3031	0.4924	1.0840	0.099*
C14	0.0135 (8)	0.5154 (3)	1.01708 (19)	0.0850 (10)
H14A	−0.0514	0.5687	1.0426	0.102*
C15	−0.1010 (7)	0.4823 (2)	0.95475 (19)	0.0837 (10)
H15A	−0.2430	0.5138	0.9377	0.100*
C16	−0.0087 (7)	0.4027 (2)	0.91673 (17)	0.0728 (9)
H16A	−0.0901	0.3806	0.8747	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1160 (19)	0.0688 (12)	0.0671 (12)	−0.0137 (14)	0.0099 (14)	0.0117 (10)
O2	0.209 (4)	0.0731 (15)	0.1115 (19)	−0.035 (2)	0.007 (2)	0.0166 (14)
O3	0.0670 (13)	0.0739 (12)	0.0642 (11)	−0.0083 (11)	−0.0064 (11)	0.0192 (10)
O4A	0.101 (6)	0.226 (14)	0.253 (17)	−0.064 (8)	−0.074 (8)	0.174 (13)
O4B	0.053 (3)	0.179 (8)	0.059 (4)	−0.011 (4)	0.018 (2)	0.033 (4)
C2	0.152 (4)	0.0581 (19)	0.072 (2)	−0.005 (3)	−0.012 (3)	0.0162 (17)
C3	0.128 (3)	0.070 (2)	0.079 (2)	0.022 (2)	−0.001 (3)	0.0025 (18)
C4	0.088 (2)	0.091 (2)	0.072 (2)	0.020 (2)	−0.0027 (19)	0.0021 (18)
C5	0.068 (2)	0.0650 (17)	0.0623 (17)	0.0010 (16)	−0.0056 (17)	0.0084 (14)
C6	0.081 (2)	0.0629 (17)	0.0598 (17)	0.0015 (18)	−0.0074 (17)	0.0068 (14)
C7	0.064 (2)	0.107 (3)	0.0669 (19)	−0.007 (2)	0.0008 (19)	0.0273 (18)
C8	0.076 (2)	0.088 (2)	0.068 (2)	0.007 (2)	−0.0060 (18)	0.0095 (17)
C9	0.076 (2)	0.0732 (17)	0.0574 (16)	−0.0006 (18)	−0.0056 (17)	0.0071 (14)
C10	0.076 (2)	0.0643 (16)	0.0602 (17)	−0.0003 (17)	−0.0015 (17)	0.0153 (14)
C11	0.0674 (19)	0.0642 (16)	0.0535 (16)	−0.0119 (16)	0.0021 (15)	0.0124 (13)
C12	0.079 (2)	0.0772 (19)	0.0618 (17)	−0.0095 (18)	−0.0037 (18)	0.0102 (15)
C13	0.107 (3)	0.077 (2)	0.0635 (18)	−0.020 (2)	−0.003 (2)	0.0005 (16)
C14	0.105 (3)	0.075 (2)	0.076 (2)	−0.006 (2)	0.015 (2)	−0.0010 (18)
C15	0.082 (2)	0.083 (2)	0.086 (2)	0.003 (2)	0.000 (2)	0.0089 (19)
C16	0.078 (2)	0.0740 (19)	0.0669 (18)	−0.0040 (19)	−0.0051 (18)	0.0008 (16)

Geometric parameters (Å, º)

O1—C2	1.347 (4)	C8—H8B	0.9600
O1—C6	1.459 (4)	C8—H8C	0.9600
O2—C2	1.201 (5)	C9—C10	1.312 (4)
O3—C7	1.305 (3)	C9—H9A	0.9300
O3—C5	1.450 (3)	C10—C11	1.463 (4)
O4A—C7	1.270 (9)	C10—H10A	0.9300
O4B—C7	1.209 (6)	C11—C16	1.383 (4)
C2—C3	1.469 (6)	C11—C12	1.391 (4)
C3—C4	1.308 (5)	C12—C13	1.373 (4)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.487 (4)	C13—C14	1.366 (5)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.505 (4)	C14—C15	1.365 (5)
C5—H5A	0.9800	C14—H14A	0.9300
C6—C9	1.484 (4)	C15—C16	1.380 (4)
C6—H6A	0.9800	C15—H15A	0.9300
C7—C8	1.457 (5)	C16—H16A	0.9300
C8—H8A	0.9600
C2—O1—C6	118.0 (3)	C7—C8—H8B	109.5
C7—O3—C5	118.2 (2)	H8A—C8—H8B	109.5
O2—C2—O1	118.4 (4)	C7—C8—H8C	109.5
O2—C2—C3	124.2 (4)	H8A—C8—H8C	109.5
O1—C2—C3	117.4 (3)	H8B—C8—H8C	109.5
C4—C3—C2	121.3 (3)	C10—C9—C6	122.6 (3)
C4—C3—H3A	119.4	C10—C9—H9A	118.7
C2—C3—H3A	119.4	C6—C9—H9A	118.7
C3—C4—C5	119.8 (4)	C9—C10—C11	128.6 (3)
C3—C4—H4A	120.1	C9—C10—H10A	115.7
C5—C4—H4A	120.1	C11—C10—H10A	115.7
O3—C5—C4	110.3 (3)	C16—C11—C12	117.5 (3)
O3—C5—C6	107.1 (3)	C16—C11—C10	123.0 (3)
C4—C5—C6	108.6 (3)	C12—C11—C10	119.5 (3)
O3—C5—H5A	110.3	C13—C12—C11	121.6 (3)
C4—C5—H5A	110.3	C13—C12—H12A	119.2
C6—C5—H5A	110.3	C11—C12—H12A	119.2
O1—C6—C9	107.3 (3)	C14—C13—C12	119.9 (3)
O1—C6—C5	110.5 (2)	C14—C13—H13A	120.1
C9—C6—C5	114.8 (2)	C12—C13—H13A	120.1
O1—C6—H6A	108.0	C15—C14—C13	119.7 (4)
C9—C6—H6A	108.0	C15—C14—H14A	120.2
C5—C6—H6A	108.0	C13—C14—H14A	120.2
O4B—C7—O4A	51.5 (10)	C14—C15—C16	120.9 (4)
O4B—C7—O3	117.1 (5)	C14—C15—H15A	119.6
O4A—C7—O3	114.8 (8)	C16—C15—H15A	119.6
O4B—C7—C8	123.2 (4)	C15—C16—C11	120.5 (3)
O4A—C7—C8	121.2 (5)	C15—C16—H16A	119.8
O3—C7—C8	114.5 (3)	C11—C16—H16A	119.8
C7—C8—H8A	109.5
C6—O1—C2—O2	174.5 (3)	C5—O3—C7—O4A	−33.3 (15)
C6—O1—C2—C3	−9.1 (4)	C5—O3—C7—C8	179.9 (3)
O2—C2—C3—C4	157.3 (4)	O1—C6—C9—C10	116.9 (3)
O1—C2—C3—C4	−18.9 (6)	C5—C6—C9—C10	−119.9 (3)
C2—C3—C4—C5	6.3 (6)	C6—C9—C10—C11	178.2 (3)
C7—O3—C5—C4	−85.8 (4)	C9—C10—C11—C16	1.8 (5)
C7—O3—C5—C6	156.3 (3)	C9—C10—C11—C12	−178.4 (3)
C3—C4—C5—O3	−87.0 (4)	C16—C11—C12—C13	−0.1 (4)
C3—C4—C5—C6	30.1 (5)	C10—C11—C12—C13	−179.9 (3)
C2—O1—C6—C9	171.5 (3)	C11—C12—C13—C14	0.1 (5)
C2—O1—C6—C5	45.7 (4)	C12—C13—C14—C15	−0.4 (5)
O3—C5—C6—O1	64.8 (3)	C13—C14—C15—C16	0.7 (5)
C4—C5—C6—O1	−54.3 (4)	C14—C15—C16—C11	−0.7 (5)
O3—C5—C6—C9	−56.6 (3)	C12—C11—C16—C15	0.4 (4)
C4—C5—C6—C9	−175.7 (3)	C10—C11—C16—C15	−179.8 (3)
C5—O3—C7—O4B	24.4 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O4B^i	0.96	2.59	3.120 (8)	115
C8—H8B···O4B^ii	0.96	2.59	3.382 (6)	140
C8—H8C···O2^iii	0.96	2.43	3.315 (4)	153

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