2-Methacryloxytropone

Kubo, K.; Fukeda, E.; Matsumoto, T.; Endo, K.; Mori, A.

doi:10.1107/S1600536806023282

2-Methacryloxytropone

K. Kubo, E. Fukeda, T. Matsumoto, K. Endo and A. Mori

The title compound, 7-oxo-1,3,5-cycloheptatrien-1-yl 2-methyl-2-propenoate, C₁₁H₁₀O₃, is known as an intermediate for the synthesis of biologically active polymers. In its crystal structure, the tropolone ring forms a dihedral angle of 69.76 (2)° with the ester plane, and intermolecular C—H

π and C—H

O interactions are observed.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023282/bi2021sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023282/bi2021Isup2.hkl Contains datablock I

CCDC reference: 613581

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.037
wR factor = 0.128
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.643     0.885
            Tmin(prime) and Tmax expected:      0.763     0.885
            RR(prime) =      0.842
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.82
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C11     ..       6.11 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  C10     ..       2.84 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O2      ..       2.71 Ang.

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

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

7-oxo-1,3,5-cycloheptatrien-1-yl 2-methyl-2-propenoate top

Crystal data top

C₁₁H₁₀O₃	F(000) = 400.00
M_r = 190.20	D_x = 1.349 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 11304 reflections
a = 6.1152 (14) Å	θ = 3.0–68.2°
b = 10.214 (2) Å	µ = 0.82 mm⁻¹
c = 15.113 (3) Å	T = 173 K
β = 97.263 (15)°	Block, colorless
V = 936.4 (3) Å³	0.30 × 0.20 × 0.15 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	1441 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.025
φ scans	θ_max = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→7
T_min = 0.643, T_max = 0.885	k = −12→12
11901 measured reflections	l = −18→18
1702 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[0.0021F_o² + σ(F_o²)]/(4F_o²)
wR(F²) = 0.128	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.24 e Å⁻³
1702 reflections	Δρ_min = −0.23 e Å⁻³
137 parameters

Special details top

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.3947 (2)	0.31839 (10)	0.53036 (8)	0.0418 (3)
O2	0.16313 (16)	0.14077 (9)	0.60396 (6)	0.0324 (2)
O3	0.47643 (17)	0.16090 (9)	0.69880 (6)	0.0337 (2)
C1	0.2569 (2)	0.36302 (12)	0.57487 (9)	0.0289 (3)
C2	0.1143 (2)	0.27239 (12)	0.61691 (9)	0.0268 (3)
C3	−0.0669 (2)	0.29473 (12)	0.65751 (10)	0.0310 (3)
C4	−0.1702 (2)	0.41471 (13)	0.67546 (10)	0.0336 (4)
C5	−0.1008 (2)	0.53816 (13)	0.66175 (10)	0.0348 (4)
C6	0.0907 (2)	0.57675 (13)	0.62400 (10)	0.0370 (4)
C7	0.2407 (2)	0.50442 (12)	0.58727 (10)	0.0340 (4)
C8	0.3650 (2)	0.09817 (12)	0.64286 (9)	0.0266 (3)
C9	0.4236 (2)	−0.03318 (12)	0.61044 (9)	0.0281 (3)
C10	0.2819 (2)	−0.10065 (13)	0.55260 (11)	0.0372 (4)
C11	0.6456 (2)	−0.08180 (13)	0.64576 (12)	0.0425 (4)
H1	−0.1360	0.2183	0.6767	0.037*
H2	−0.3052	0.4076	0.7001	0.041*
H3	−0.1905	0.6070	0.6794	0.042*
H4	0.1184	0.6683	0.6251	0.045*
H5	0.3545	0.5536	0.5655	0.041*
H6	0.1410	−0.0650	0.5323	0.045*
H7	0.3224	−0.1839	0.5319	0.045*
H8	0.6638	−0.0788	0.7091	0.051*
H9	0.7540	−0.0283	0.6239	0.052*
H10	0.6617	−0.1695	0.6266	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0431 (7)	0.0399 (6)	0.0464 (6)	0.0076 (5)	0.0211 (5)	−0.0006 (4)
O2	0.0251 (6)	0.0250 (5)	0.0459 (6)	0.0022 (4)	0.0001 (4)	−0.0054 (4)
O3	0.0294 (6)	0.0336 (5)	0.0372 (5)	−0.0006 (4)	0.0018 (4)	−0.0022 (4)
C1	0.0279 (8)	0.0300 (7)	0.0289 (7)	0.0037 (5)	0.0043 (5)	−0.0001 (5)
C2	0.0243 (7)	0.0231 (6)	0.0319 (7)	0.0016 (5)	−0.0005 (5)	−0.0040 (5)
C3	0.0258 (8)	0.0292 (7)	0.0379 (7)	−0.0022 (5)	0.0037 (6)	−0.0006 (5)
C4	0.0266 (8)	0.0389 (8)	0.0362 (8)	0.0041 (6)	0.0073 (6)	−0.0032 (5)
C5	0.0370 (9)	0.0316 (7)	0.0364 (7)	0.0089 (6)	0.0072 (6)	−0.0029 (5)
C6	0.0464 (10)	0.0262 (7)	0.0391 (8)	0.0012 (6)	0.0088 (7)	0.0001 (5)
C7	0.0368 (9)	0.0295 (7)	0.0369 (8)	−0.0022 (6)	0.0100 (6)	0.0033 (5)
C8	0.0240 (7)	0.0265 (6)	0.0302 (7)	−0.0009 (5)	0.0075 (5)	0.0045 (5)
C9	0.0288 (8)	0.0250 (6)	0.0318 (7)	0.0013 (5)	0.0087 (5)	0.0051 (5)
C10	0.0381 (9)	0.0293 (7)	0.0443 (8)	0.0017 (6)	0.0061 (7)	−0.0042 (6)
C11	0.0451 (11)	0.0352 (8)	0.0458 (9)	0.0093 (7)	0.0011 (7)	0.0005 (6)

Geometric parameters (Å, º) top

O1—C1	1.2304 (19)	C9—C10	1.341 (2)
O2—C2	1.3962 (16)	C9—C11	1.480 (2)
O2—C8	1.3692 (16)	C3—H1	0.950
O3—C8	1.2018 (16)	C4—H2	0.950
C1—C2	1.470 (2)	C5—H3	0.950
C1—C7	1.4613 (18)	C6—H4	0.950
C2—C3	1.353 (2)	C7—H5	0.950
C3—C4	1.420 (2)	C10—H6	0.950
C4—C5	1.355 (2)	C10—H7	0.950
C5—C6	1.422 (2)	C11—H8	0.950
C6—C7	1.350 (2)	C11—H9	0.950
C8—C9	1.4876 (19)	C11—H10	0.950

O1···C4ⁱ	3.3735 (18)	H1···H7^v	3.233
O1···C5ⁱⁱ	3.5339 (18)	H1···H8^vii	3.332
O1···C7ⁱⁱⁱ	3.5227 (19)	H1···H9^vii	2.701
O1···C10^iv	3.3252 (19)	H2···O1^vii	3.096
O1···C11^iv	3.5804 (19)	H2···O3^vii	2.851
O2···C10^v	3.3977 (18)	H2···O3^viii	3.245
O3···C3ⁱ	3.2397 (18)	H2···C1^vii	3.111
O3···C4ⁱ	3.4215 (17)	H2···C7^vii	3.225
O3···C5^vi	3.5377 (19)	H2···C8^viii	3.127
C1···C6ⁱⁱ	3.5093 (19)	H2···C9^viii	3.101
C3···O3^vii	3.2397 (18)	H2···C11^viii	3.317
C4···O1^vii	3.3735 (18)	H2···H5^vii	3.102
C4···O3^vii	3.4215 (17)	H2···H8^viii	2.734
C5···O1ⁱⁱ	3.5339 (18)	H3···O1ⁱⁱ	3.344
C5···O3^viii	3.5377 (19)	H3···O2^viii	3.276
C5···C8^viii	3.593 (2)	H3···O3^viii	2.751
C6···C1ⁱⁱ	3.5093 (19)	H3···C2^viii	3.492
C7···O1ⁱⁱⁱ	3.5227 (19)	H3···C3^viii	3.355
C8···C5^vi	3.593 (2)	H3···C8^viii	3.015
C9···C10^iv	3.508 (2)	H3···C11^xi	3.353
C10···O1^iv	3.3252 (19)	H3···H1^viii	2.986
C10···O2^v	3.3977 (18)	H3···H5^vii	3.129
C10···C9^iv	3.508 (2)	H3···H8^xi	3.376
C11···O1^iv	3.5804 (19)	H3···H10^xi	2.546
O1···H1ⁱ	3.545	H4···O3^x	3.400
O1···H2ⁱ	3.096	H4···C1ⁱⁱ	3.571
O1···H3ⁱⁱ	3.344	H4···C3^viii	3.580
O1···H5ⁱⁱⁱ	2.593	H4···C9^xii	3.596
O1···H7^iv	2.485	H4···C10^xii	2.837
O1···H10^iv	2.803	H4···H1^viii	3.027
O2···H3^vi	3.276	H4···H6^xii	3.075
O2···H6^v	2.707	H4···H7^xii	2.503
O2···H7^v	3.418	H4···H10^xi	3.250
O2···H9^vii	3.086	H5···O1ⁱⁱⁱ	2.593
O3···H1ⁱ	2.504	H5···C1ⁱⁱⁱ	3.486
O3···H2ⁱ	2.851	H5···C4ⁱ	3.464
O3···H2^vi	3.245	H5···C5ⁱ	3.466
O3···H3^vi	2.751	H5···C10^xii	3.562
O3···H4^ix	3.400	H5···H2ⁱ	3.102
O3···H8^x	3.169	H5···H3ⁱ	3.129
O3···H10^x	3.353	H5···H5ⁱⁱⁱ	3.029
C1···H2ⁱ	3.111	H5···H7^xii	2.731
C1···H4ⁱⁱ	3.571	H5···H10^xii	3.456
C1···H5ⁱⁱⁱ	3.486	H6···O2^v	2.707
C1···H8^x	3.294	H6···C2^v	3.334
C2···H3^vi	3.492	H6···C10^v	3.218
C2···H6^v	3.334	H6···C11^iv	3.476
C2···H7^v	3.389	H6···H1^v	3.522
C2···H8^x	3.188	H6···H4^xiii	3.075
C3···H3^vi	3.355	H6···H6^v	2.294
C3···H4^vi	3.580	H6···H9^vii	2.914
C3···H7^v	3.284	H6···H9^iv	2.698
C3···H8^x	3.248	H6···H10^vii	3.580
C3···H9^vii	3.493	H7···O1^iv	2.485
C4···H5^vii	3.464	H7···O2^v	3.418
C4···H8^x	3.357	H7···C2^v	3.389
C5···H1^viii	3.248	H7···C3^v	3.284
C5···H5^vii	3.466	H7···C6^xiii	3.228
C5···H8^x	3.325	H7···C7^xiii	3.345
C5···H10^xi	3.334	H7···C8^iv	3.560
C6···H1^viii	3.321	H7···C9^iv	3.578
C6···H7^xii	3.228	H7···H1^v	3.233
C6···H8^x	3.191	H7···H4^xiii	2.503
C7···H2ⁱ	3.225	H7···H5^xiii	2.731
C7···H7^xii	3.345	H7···H9^iv	3.191
C7···H8^x	3.175	H8···O3^ix	3.169
C8···H1ⁱ	3.269	H8···C1^ix	3.294
C8···H2^vi	3.127	H8···C2^ix	3.188
C8···H3^vi	3.015	H8···C3^ix	3.248
C8···H7^iv	3.560	H8···C4^ix	3.357
C9···H2^vi	3.101	H8···C5^ix	3.325
C9···H4^xiii	3.596	H8···C6^ix	3.191
C9···H7^iv	3.578	H8···C7^ix	3.175
C10···H4^xiii	2.837	H8···H1ⁱ	3.332
C10···H5^xiii	3.562	H8···H2^vi	2.734
C10···H6^v	3.218	H8···H3^xiv	3.376
C10···H9^iv	2.958	H9···O2ⁱ	3.086
C11···H1ⁱ	3.353	H9···C3ⁱ	3.493
C11···H2^vi	3.317	H9···C10^iv	2.958
C11···H3^xiv	3.353	H9···H1ⁱ	2.701
C11···H6^iv	3.476	H9···H6ⁱ	2.914
H1···O1^vii	3.545	H9···H6^iv	2.698
H1···O3^vii	2.504	H9···H7^iv	3.191
H1···C5^vi	3.248	H10···O1^iv	2.803
H1···C6^vi	3.321	H10···O3^ix	3.353
H1···C8^vii	3.269	H10···C5^xiv	3.334
H1···C11^vii	3.353	H10···H3^xiv	2.546
H1···H3^vi	2.986	H10···H4^xiv	3.250
H1···H4^vi	3.027	H10···H5^xiii	3.456
H1···H6^v	3.522	H10···H6ⁱ	3.580

C2—O2—C8	116.28 (10)	C4—C3—H1	115.1
O1—C1—C2	119.19 (12)	C3—C4—H2	116.0
O1—C1—C7	119.90 (13)	C5—C4—H2	115.8
C2—C1—C7	120.89 (13)	C4—C5—H3	116.2
O2—C2—C1	113.38 (12)	C6—C5—H3	116.2
O2—C2—C3	115.34 (12)	C5—C6—H4	114.8
C1—C2—C3	130.90 (12)	C7—C6—H4	114.7
C2—C3—C4	129.93 (13)	C1—C7—H5	114.4
C3—C4—C5	128.18 (14)	C6—C7—H5	114.7
C4—C5—C6	127.56 (14)	C9—C10—H6	119.9
C5—C6—C7	130.53 (13)	C9—C10—H7	120.1
C1—C7—C6	130.84 (14)	H6—C10—H7	120.0
O2—C8—O3	122.21 (12)	C9—C11—H8	109.8
O2—C8—C9	112.76 (10)	C9—C11—H9	109.3
O3—C8—C9	125.00 (12)	C9—C11—H10	109.4
C8—C9—C10	121.02 (12)	H8—C11—H9	109.5
C8—C9—C11	115.59 (11)	H8—C11—H10	109.5
C10—C9—C11	123.38 (13)	H9—C11—H10	109.5
C2—C3—H1	114.9

C2—O2—C8—O3	14.13 (19)	O2—C2—C3—C4	−175.46 (13)
C2—O2—C8—C9	−167.73 (11)	C1—C2—C3—C4	−3.1 (2)
C8—O2—C2—C1	65.47 (15)	C2—C3—C4—C5	−5.5 (2)
C8—O2—C2—C3	−120.83 (13)	C3—C4—C5—C6	1.6 (2)
O1—C1—C2—O2	3.10 (17)	C4—C5—C6—C7	5.2 (2)
O1—C1—C2—C3	−169.36 (14)	C5—C6—C7—C1	−0.6 (2)
O1—C1—C7—C6	171.78 (15)	O2—C8—C9—C10	−3.1 (2)
C2—C1—C7—C6	−9.9 (2)	O2—C8—C9—C11	176.49 (12)
C7—C1—C2—O2	−175.27 (11)	O3—C8—C9—C10	174.94 (15)
C7—C1—C2—C3	12.3 (2)	O3—C8—C9—C11	−5.4 (2)

Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y, −z+1; (vi) −x, y−1/2, −z+3/2; (vii) x−1, y, z; (viii) −x, y+1/2, −z+3/2; (ix) −x+1, y−1/2, −z+3/2; (x) −x+1, y+1/2, −z+3/2; (xi) x−1, y+1, z; (xii) x, y+1, z; (xiii) x, y−1, z; (xiv) x+1, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H4···C10^xii	0.95	2.84	3.702 (2)	152
C3—H1···O3^vii	0.95	2.51	3.240 (2)	134
C7—H5···O1ⁱⁱⁱ	0.95	2.59	3.523 (2)	166
C10—H6···O2^v	0.95	2.71	3.398 (2)	130
C10—H7···O1^iv	0.95	2.49	3.325 (2)	147

Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y, −z+1; (vii) x−1, y, z; (xii) x, y+1, z.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page