3-[(7-Acetoxy-4-methyl­coumarin-8-yl)­methyl]­sydnone

In the title compound, C₁₅H₁₂N₂O₆, the sydnone ring is oriented nearly perpendicular to the plane of the coumarin moiety. Weak intermolecular C—H...O interactions link the mol­ecules into a complex network that can be described by C(X) chains (X is 6, 8 and 9) and R₂²(20) rings.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.052
• wR factor = 0.151
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.07; Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

3-[(7-Acetoxy-4-methylcoumarin-8-yl)methyl]sydnone

Crystal data

C15H12N2O6	F(000) = 656
Mr = 316.27	Dx = 1.515 Mg m^−3
Monoclinic, P21/c	Melting point: 453 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.5067 (3) Å	Cell parameters from 4215 reflections
b = 13.1916 (3) Å	θ = 2.0–30.0°
c = 9.1773 (2) Å	µ = 0.12 mm^−1
β = 95.6210 (9)°	T = 160 K
V = 1386.34 (6) Å^3	Plate, colourless
Z = 4	0.30 × 0.30 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer	2403 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generator	Rint = 0.074
Horizontally mounted graphite crystal monochromator	θmax = 30.1°, θmin = 2.4°
Detector resolution: 9 pixels mm^-1	h = −16→16
φ and ω scans with κ offsets	k = −18→18
37980 measured reflections	l = −12→12
4057 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0787P)^2] where P = (Fo^2 + 2Fc^2)/3
4056 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. Solvent used: EtOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.480 (2) Frames collected: 365 Seconds exposure per frame: 70 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0

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	Occ. (<1)
O1	−0.07150 (10)	0.78831 (9)	0.71598 (13)	0.0416 (3)
O5	−0.01852 (11)	0.62444 (10)	0.76255 (14)	0.0482 (4)
O7	0.32463 (8)	0.88113 (8)	0.38560 (10)	0.0269 (3)
O8	0.35704 (10)	0.85699 (9)	0.15564 (11)	0.0355 (3)
O17	0.23299 (8)	0.94056 (8)	0.86835 (10)	0.0292 (3)
O18	0.32391 (10)	1.08542 (9)	0.94514 (12)	0.0402 (3)
N2	−0.02385 (12)	0.87568 (11)	0.66406 (17)	0.0406 (4)
N3	0.07899 (10)	0.84738 (10)	0.63153 (12)	0.0257 (3)
C4	0.10404 (14)	0.75012 (13)	0.65718 (17)	0.0342 (4)
H4	0.1740	0.7163	0.6389	0.041*
C5	0.00780 (14)	0.70709 (14)	0.71622 (17)	0.0341 (4)
C6	0.15271 (12)	0.92676 (12)	0.57322 (16)	0.0264 (4)
H61	0.1270	0.9942	0.6047	0.032*
H62	0.1429	0.9248	0.4649	0.032*
C8	0.40094 (14)	0.86302 (12)	0.28088 (16)	0.0275 (4)
C9	0.52294 (14)	0.85316 (12)	0.33010 (16)	0.0278 (4)
H9	0.5767	0.8431	0.2593	0.033*
C10	0.56412 (13)	0.85766 (11)	0.47265 (16)	0.0256 (4)
C11	0.51503 (13)	0.88560 (12)	0.73097 (16)	0.0263 (4)
H11	0.5945	0.8763	0.7671	0.032*
C12	0.43408 (13)	0.90712 (12)	0.82759 (16)	0.0275 (4)
H12	0.4573	0.9123	0.9295	0.033*
C13	0.31873 (13)	0.92112 (11)	0.77440 (15)	0.0252 (4)
C14	0.27951 (13)	0.91180 (11)	0.62612 (15)	0.0236 (3)
C15	0.36377 (13)	0.88896 (11)	0.53197 (15)	0.0233 (3)
C16	0.48235 (13)	0.87709 (11)	0.58034 (15)	0.0239 (3)
C18	0.24699 (14)	1.02529 (13)	0.95581 (15)	0.0304 (4)
C19	0.15652 (14)	1.03050 (16)	1.05881 (17)	0.0409 (5)
H191	0.1278	0.9621	1.0764	0.061*	0.48 (2)
H192	0.0917	1.0729	1.0169	0.061*	0.48 (2)
H193	0.1900	1.0600	1.1516	0.061*	0.48 (2)
H194	0.1452	1.1012	1.0869	0.061*	0.52 (2)
H195	0.1813	0.9904	1.1463	0.061*	0.52 (2)
H196	0.0830	1.0033	1.0117	0.061*	0.52 (2)
C20	0.69155 (14)	0.84352 (13)	0.52021 (18)	0.0333 (4)
H201	0.7345	0.8360	0.4338	0.050*
H202	0.7023	0.7826	0.5811	0.050*
H203	0.7211	0.9027	0.5768	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0323 (7)	0.0370 (7)	0.0578 (8)	−0.0011 (6)	0.0157 (6)	0.0057 (6)
O5	0.0455 (8)	0.0379 (8)	0.0618 (8)	−0.0080 (6)	0.0084 (6)	0.0138 (6)
O7	0.0250 (6)	0.0332 (7)	0.0227 (5)	−0.0001 (5)	0.0030 (4)	−0.0011 (4)
O8	0.0355 (7)	0.0466 (8)	0.0248 (6)	−0.0058 (5)	0.0052 (5)	−0.0025 (5)
O17	0.0264 (6)	0.0359 (7)	0.0259 (5)	−0.0027 (5)	0.0054 (4)	−0.0036 (5)
O18	0.0409 (7)	0.0358 (7)	0.0455 (7)	−0.0047 (6)	0.0125 (6)	−0.0085 (5)
N2	0.0307 (8)	0.0336 (9)	0.0600 (10)	0.0008 (7)	0.0174 (7)	0.0033 (7)
N3	0.0212 (7)	0.0286 (8)	0.0272 (7)	0.0008 (5)	0.0018 (5)	−0.0009 (5)
C4	0.0278 (9)	0.0287 (9)	0.0463 (9)	0.0041 (7)	0.0054 (7)	0.0032 (7)
C5	0.0305 (9)	0.0349 (10)	0.0366 (9)	0.0004 (8)	0.0013 (7)	0.0029 (7)
C6	0.0262 (8)	0.0262 (9)	0.0267 (8)	−0.0010 (7)	0.0027 (6)	0.0025 (6)
C8	0.0319 (9)	0.0254 (9)	0.0261 (8)	−0.0031 (7)	0.0079 (7)	−0.0005 (6)
C9	0.0273 (8)	0.0255 (9)	0.0317 (8)	−0.0022 (7)	0.0090 (7)	−0.0027 (6)
C10	0.0246 (8)	0.0183 (8)	0.0344 (8)	−0.0013 (6)	0.0053 (7)	0.0000 (6)
C11	0.0222 (8)	0.0248 (8)	0.0314 (8)	−0.0010 (6)	−0.0001 (6)	0.0017 (6)
C12	0.0282 (9)	0.0299 (9)	0.0239 (7)	−0.0012 (7)	0.0003 (6)	0.0006 (6)
C13	0.0263 (8)	0.0244 (8)	0.0254 (8)	−0.0028 (6)	0.0056 (6)	−0.0005 (6)
C14	0.0222 (8)	0.0230 (8)	0.0256 (8)	−0.0015 (6)	0.0028 (6)	0.0010 (6)
C15	0.0272 (8)	0.0197 (8)	0.0227 (7)	−0.0019 (6)	0.0009 (6)	0.0005 (6)
C16	0.0240 (8)	0.0198 (8)	0.0278 (8)	−0.0012 (6)	0.0032 (6)	0.0022 (6)
C18	0.0307 (9)	0.0349 (9)	0.0253 (8)	0.0021 (8)	0.0014 (6)	−0.0015 (7)
C19	0.0342 (10)	0.0524 (12)	0.0374 (9)	0.0021 (8)	0.0104 (7)	−0.0091 (8)
C20	0.0289 (9)	0.0311 (9)	0.0406 (9)	0.0024 (7)	0.0069 (7)	0.0002 (7)

Geometric parameters (Å, º)

O1—N2	1.3809 (18)	C10—C16	1.453 (2)
O1—C5	1.407 (2)	C10—C20	1.500 (2)
O5—C5	1.219 (2)	C11—C12	1.377 (2)
O7—C15	1.3782 (16)	C11—C16	1.4010 (19)
O7—C8	1.3845 (17)	C11—H11	0.9500
O8—C8	1.2119 (17)	C12—C13	1.381 (2)
O17—C18	1.3763 (19)	C12—H12	0.9500
O17—C13	1.3961 (17)	C13—C14	1.3965 (19)
O18—C18	1.1997 (19)	C14—C15	1.393 (2)
N2—N3	1.3031 (18)	C15—C16	1.402 (2)
N3—C4	1.331 (2)	C18—C19	1.475 (2)
N3—C6	1.4803 (19)	C19—H191	0.9800
C4—C5	1.400 (2)	C19—H192	0.9800
C4—H4	0.9500	C19—H193	0.9800
C6—C14	1.5049 (19)	C19—H194	0.9800
C6—H61	0.9900	C19—H195	0.9800
C6—H62	0.9900	C19—H196	0.9800
C8—C9	1.438 (2)	C20—H201	0.9800
C9—C10	1.348 (2)	C20—H202	0.9800
C9—H9	0.9500	C20—H203	0.9800
N2—O1—C5	110.90 (12)	C15—C14—C6	122.67 (13)
C15—O7—C8	121.37 (11)	C13—C14—C6	120.89 (13)
C18—O17—C13	117.38 (12)	O7—C15—C14	116.09 (12)
N3—N2—O1	103.90 (12)	O7—C15—C16	121.02 (13)
N2—N3—C4	114.92 (13)	C14—C15—C16	122.87 (13)
N2—N3—C6	116.47 (13)	C11—C16—C15	117.54 (13)
C4—N3—C6	128.61 (13)	C11—C16—C10	123.80 (13)
N3—C4—C5	107.07 (14)	C15—C16—C10	118.66 (13)
N3—C4—H4	126.5	O18—C18—O17	122.31 (13)
C5—C4—H4	126.5	O18—C18—C19	126.46 (15)
O5—C5—C4	136.93 (17)	O17—C18—C19	111.23 (14)
O5—C5—O1	119.88 (15)	C18—C19—H191	109.5
C4—C5—O1	103.18 (14)	C18—C19—H192	109.5
N3—C6—C14	111.25 (12)	H191—C19—H192	109.5
N3—C6—H61	109.4	C18—C19—H193	109.5
C14—C6—H61	109.4	H191—C19—H193	109.5
N3—C6—H62	109.4	H192—C19—H193	109.5
C14—C6—H62	109.4	C18—C19—H194	109.5
H61—C6—H62	108.0	H191—C19—H194	141.1
O8—C8—O7	115.85 (13)	H192—C19—H194	56.3
O8—C8—C9	126.54 (14)	H193—C19—H194	56.3
O7—C8—C9	117.61 (12)	C18—C19—H195	109.5
C10—C9—C8	122.71 (14)	H191—C19—H195	56.3
C10—C9—H9	118.6	H192—C19—H195	141.1
C8—C9—H9	118.6	H193—C19—H195	56.3
C9—C10—C16	118.58 (14)	H194—C19—H195	109.5
C9—C10—C20	121.17 (14)	C18—C19—H196	109.5
C16—C10—C20	120.25 (13)	H191—C19—H196	56.3
C12—C11—C16	121.25 (14)	H192—C19—H196	56.3
C12—C11—H11	119.4	H193—C19—H196	141.1
C16—C11—H11	119.4	H194—C19—H196	109.5
C11—C12—C13	119.16 (13)	H195—C19—H196	109.5
C11—C12—H12	120.4	C10—C20—H201	109.5
C13—C12—H12	120.4	C10—C20—H202	109.5
C12—C13—O17	121.27 (12)	H201—C20—H202	109.5
C12—C13—C14	122.71 (13)	C10—C20—H203	109.5
O17—C13—C14	115.94 (13)	H201—C20—H203	109.5
C15—C14—C13	116.44 (13)	H202—C20—H203	109.5
C5—O1—N2—N3	1.26 (17)	O17—C13—C14—C15	−177.88 (12)
O1—N2—N3—C4	−0.16 (17)	C12—C13—C14—C6	179.42 (14)
O1—N2—N3—C6	−179.45 (11)	O17—C13—C14—C6	2.6 (2)
N2—N3—C4—C5	−0.98 (19)	N3—C6—C14—C15	115.18 (15)
C6—N3—C4—C5	178.20 (13)	N3—C6—C14—C13	−65.31 (18)
N3—C4—C5—O5	−178.12 (19)	C8—O7—C15—C14	177.21 (13)
N3—C4—C5—O1	1.62 (17)	C8—O7—C15—C16	−1.1 (2)
N2—O1—C5—O5	177.99 (14)	C13—C14—C15—O7	−179.22 (12)
N2—O1—C5—C4	−1.80 (17)	C6—C14—C15—O7	0.3 (2)
N2—N3—C6—C14	144.08 (13)	C13—C14—C15—C16	−0.9 (2)
C4—N3—C6—C14	−35.1 (2)	C6—C14—C15—C16	178.60 (14)
C15—O7—C8—O8	179.60 (13)	C12—C11—C16—C15	−1.5 (2)
C15—O7—C8—C9	−0.3 (2)	C12—C11—C16—C10	178.02 (14)
O8—C8—C9—C10	−177.78 (15)	O7—C15—C16—C11	−179.65 (12)
O7—C8—C9—C10	2.1 (2)	C14—C15—C16—C11	2.1 (2)
C8—C9—C10—C16	−2.4 (2)	O7—C15—C16—C10	0.8 (2)
C8—C9—C10—C20	177.90 (13)	C14—C15—C16—C10	−177.36 (14)
C16—C11—C12—C13	−0.4 (2)	C9—C10—C16—C11	−178.59 (15)
C11—C12—C13—O17	178.38 (14)	C20—C10—C16—C11	1.1 (2)
C11—C12—C13—C14	1.7 (2)	C9—C10—C16—C15	0.9 (2)
C18—O17—C13—C12	59.09 (19)	C20—C10—C16—C15	−179.40 (14)
C18—O17—C13—C14	−124.02 (14)	C13—O17—C18—O18	5.9 (2)
C12—C13—C14—C15	−1.0 (2)	C13—O17—C18—C19	−174.43 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O8^i	0.95	2.31	3.237 (2)	166
C6—H61···O5^ii	0.99	2.51	3.451 (2)	159
C6—H62···O5^iii	0.99	2.58	3.3715 (19)	137
C9—H9···O18^iv	0.95	2.48	3.319 (2)	148
C12—H12···O8^v	0.95	2.58	3.2878 (18)	132
C19—H194···O1^vi	0.98	2.53	3.367 (2)	143

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