5-Methyl­tropolone

The title compound [systematic name: 2-hydr­oxy-5-methyl-2,4,6-cyclo­hepta­trien-1-one], C₈H₈O₂, has two independent mol­ecules in the asymmetric unit, which are linked into a dimer by a pair of inter­molecular O—H...O hydrogen bonds. The crystal packing is consolidated by π–π, C—H...π and C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.039
• wR factor = 0.109
• Data-to-parameter ratio = 15.0

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Computing details

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Bruno et al., 2002); software used to prepare material for publication: CrystalStructure.

2-hydroxy-5-methyl-2,4,6-cycloheptatrien-1-one

Crystal data

C8H8O2	F(000) = 576.00
Mr = 136.15	Dx = 1.351 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 3212 reflections
a = 13.628 (3) Å	θ = 3.2–27.5°
b = 7.1352 (14) Å	µ = 0.10 mm^−1
c = 14.663 (3) Å	T = 153 K
β = 110.1031 (11)°	Prism, colourless
V = 1338.9 (5) Å^3	0.18 × 0.15 × 0.12 mm
Z = 8

Data collection

Rigaku Saturn diffractometer	2143 reflections with F^2 > 2σ(F^2)
Detector resolution: 7.31 pixels mm^-1	Rint = 0.036
ω scans	θmax = 27.5°
Absorption correction: multi-scan (Jacobson, 1998)	h = −17→17
Tmin = 0.939, Tmax = 0.988	k = −8→9
10387 measured reflections	l = −18→14
3054 independent reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[0.0007Fo^2 + σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.109	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.25 e Å^−3
3054 reflections	Δρmin = −0.22 e Å^−3
203 parameters

Special details

Refinement. Refinement was performed 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.70585 (7)	0.35352 (15)	0.78154 (7)	0.0346 (2)
O2	0.56648 (8)	0.37165 (15)	0.60946 (7)	0.0340 (2)
O3	0.76150 (7)	0.36046 (15)	0.59148 (7)	0.0353 (2)
O4	0.87887 (8)	0.21659 (16)	0.75555 (7)	0.0323 (2)
C1	0.61290 (10)	0.35616 (18)	0.77955 (10)	0.0248 (3)
C2	0.53141 (10)	0.36824 (19)	0.68467 (10)	0.0253 (3)
C3	0.42559 (10)	0.3786 (2)	0.66276 (10)	0.0294 (3)
C4	0.36498 (11)	0.37736 (19)	0.72344 (10)	0.0290 (3)
C5	0.39403 (11)	0.36133 (18)	0.82229 (10)	0.0266 (3)
C6	0.49885 (11)	0.34478 (19)	0.88568 (10)	0.0281 (3)
C7	0.59059 (11)	0.3442 (2)	0.86788 (10)	0.0287 (3)
C8	0.31104 (12)	0.3580 (2)	0.86874 (12)	0.0369 (4)
C9	0.84963 (10)	0.30574 (19)	0.59327 (9)	0.0248 (3)
C10	0.91986 (10)	0.22804 (19)	0.68452 (9)	0.0243 (3)
C11	1.02070 (11)	0.16859 (19)	0.70683 (10)	0.0273 (3)
C12	1.08565 (11)	0.15710 (19)	0.65003 (10)	0.0271 (3)
C13	1.06513 (10)	0.20409 (19)	0.55478 (10)	0.0257 (3)
C14	0.96811 (10)	0.27459 (19)	0.49218 (9)	0.0261 (3)
C15	0.87782 (10)	0.31644 (19)	0.50797 (9)	0.0258 (3)
C16	1.14871 (11)	0.1775 (2)	0.51031 (11)	0.0320 (3)
H1	0.6419 (17)	0.372 (3)	0.6336 (15)	0.082 (7)*
H2	0.3865	0.3892	0.5954	0.034*
H3	0.2918	0.3884	0.6904	0.035*
H4	0.5065	0.3300	0.9522	0.035*
H5	0.6512	0.3356	0.9244	0.034*
H6	0.3291	0.4428	0.9219	0.048*
H7	0.3058	0.2348	0.8913	0.048*
H8	0.2458	0.3935	0.8222	0.048*
H9	0.8106 (17)	0.265 (3)	0.7349 (15)	0.072 (6)*
H10	1.0525	0.1284	0.7722	0.033*
H11	1.1538	0.1092	0.6826	0.032*
H12	0.9656	0.2947	0.4274	0.032*
H13	0.8232	0.3611	0.4524	0.031*
H14	1.2052	0.1090	0.5539	0.041*
H15	1.1207	0.1103	0.4511	0.041*
H16	1.1729	0.2964	0.4979	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0226 (5)	0.0525 (6)	0.0307 (5)	−0.0012 (4)	0.0116 (4)	−0.0059 (4)
O2	0.0290 (5)	0.0529 (6)	0.0227 (5)	−0.0010 (4)	0.0121 (4)	0.0001 (4)
O3	0.0266 (5)	0.0508 (6)	0.0308 (5)	0.0069 (4)	0.0127 (4)	0.0052 (4)
O4	0.0316 (5)	0.0466 (6)	0.0215 (5)	0.0039 (4)	0.0128 (4)	0.0006 (4)
C1	0.0230 (6)	0.0262 (6)	0.0264 (6)	−0.0009 (5)	0.0101 (5)	−0.0033 (5)
C2	0.0283 (6)	0.0267 (6)	0.0243 (6)	−0.0019 (5)	0.0132 (5)	−0.0012 (5)
C3	0.0243 (6)	0.0386 (8)	0.0239 (6)	−0.0014 (6)	0.0066 (5)	0.0000 (6)
C4	0.0214 (6)	0.0345 (7)	0.0310 (7)	−0.0020 (5)	0.0089 (5)	−0.0014 (6)
C5	0.0268 (6)	0.0242 (6)	0.0329 (7)	−0.0010 (5)	0.0154 (5)	−0.0019 (5)
C6	0.0329 (7)	0.0323 (7)	0.0230 (6)	0.0018 (6)	0.0146 (5)	0.0000 (5)
C7	0.0256 (6)	0.0372 (7)	0.0224 (6)	0.0037 (6)	0.0070 (5)	−0.0020 (5)
C8	0.0331 (7)	0.0455 (9)	0.0391 (8)	−0.0010 (7)	0.0216 (6)	−0.0031 (7)
C9	0.0238 (6)	0.0270 (6)	0.0240 (6)	−0.0025 (5)	0.0088 (5)	−0.0018 (5)
C10	0.0281 (6)	0.0257 (6)	0.0204 (6)	−0.0023 (5)	0.0102 (5)	−0.0034 (5)
C11	0.0299 (7)	0.0326 (7)	0.0195 (6)	0.0029 (6)	0.0084 (5)	0.0019 (5)
C12	0.0249 (6)	0.0277 (7)	0.0279 (7)	0.0016 (5)	0.0079 (5)	−0.0015 (5)
C13	0.0281 (6)	0.0223 (6)	0.0287 (6)	−0.0038 (5)	0.0126 (5)	−0.0054 (5)
C14	0.0303 (7)	0.0284 (6)	0.0210 (6)	−0.0051 (5)	0.0105 (5)	−0.0026 (5)
C15	0.0257 (6)	0.0292 (7)	0.0208 (6)	−0.0032 (5)	0.0060 (5)	0.0003 (5)
C16	0.0321 (7)	0.0333 (7)	0.0366 (7)	−0.0027 (6)	0.0196 (6)	−0.0049 (6)

Geometric parameters (Å, º)

O1—C1	1.2571 (17)	C13—C16	1.506 (2)
O2—C2	1.344 (2)	C14—C15	1.361 (2)
O3—C9	1.2545 (17)	O2—H1	0.97 (2)
O4—C10	1.3429 (19)	O4—H9	0.94 (2)
C1—C2	1.4540 (16)	C3—H2	0.950
C1—C7	1.431 (2)	C4—H3	0.950
C2—C3	1.3674 (18)	C6—H4	0.950
C3—C4	1.407 (2)	C7—H5	0.950
C4—C5	1.370 (2)	C8—H6	0.950
C5—C6	1.4162 (17)	C8—H7	0.950
C5—C8	1.508 (2)	C8—H8	0.950
C6—C7	1.362 (2)	C11—H10	0.950
C9—C10	1.4606 (16)	C12—H11	0.950
C9—C15	1.431 (2)	C14—H12	0.950
C10—C11	1.3662 (19)	C15—H13	0.950
C11—C12	1.411 (2)	C16—H14	0.950
C12—C13	1.368 (2)	C16—H15	0.950
C13—C14	1.4175 (16)	C16—H16	0.950
O1···O3	3.1299 (15)	H3···C13^xii	3.317
O1···O4	2.6976 (15)	H3···C16^xii	3.082
O1···C4^i	3.5258 (17)	H3···H9^v	3.382
O1···C12^ii	3.4369 (16)	H3···H11^xii	2.716
O1···C15^iii	3.5549 (14)	H3···H13^iv	2.789
O2···O2^iv	3.5977 (13)	H3···H14^xii	2.784
O2···O3	2.7606 (15)	H3···H16^xii	2.806
O2···C6^v	3.4983 (17)	H4···O2^i	3.447
O2···C6^vi	3.4528 (17)	H4···O2^iii	2.600
O3···O1	3.1299 (15)	H4···C2^iii	3.598
O3···O2	2.7606 (15)	H4···C6^xiii	3.341
O4···O1	2.6976 (15)	H4···H1^iii	3.030
O4···C11^ii	3.4727 (17)	H4···H2^iii	3.450
O4···C12^ii	3.4014 (17)	H4···H4^xiii	2.838
O4···C14^iii	3.2589 (15)	H4···H6^xiii	2.866
C1···C3^i	3.5923 (19)	H5···O3^iii	2.772
C1···C4^i	3.4312 (18)	H5···C3^i	3.527
C2···C6^v	3.5360 (19)	H5···C9^iii	3.139
C3···C1^v	3.5923 (19)	H5···C15^iii	3.100
C3···C7^v	3.349 (2)	H5···C16^ii	3.537
C4···O1^v	3.5258 (17)	H5···H1^iii	3.448
C4···C1^v	3.4312 (18)	H5···H2^i	3.223
C6···O2^i	3.4983 (17)	H5···H6^xiii	2.690
C6···O2^iii	3.4528 (17)	H5···H13^iii	2.640
C6···C2^i	3.5360 (19)	H5···H14^ii	2.703
C7···C3^i	3.349 (2)	H5···H15^ii	3.597
C8···C16^vii	3.525 (2)	H6···O2^v	3.471
C10···C11^ii	3.4911 (18)	H6···O3^v	3.206
C11···O4^viii	3.4727 (17)	H6···C6^xiii	3.348
C11···C10^viii	3.4911 (18)	H6···C7^xiii	3.270
C12···O1^viii	3.4369 (16)	H6···C9^v	3.509
C12···O4^viii	3.4014 (17)	H6···C16^vii	3.263
C13···C13^ix	3.5005 (18)	H6···H1^v	3.227
C13···C14^ix	3.4829 (19)	H6···H2^iii	3.366
C14···O4^vi	3.2589 (15)	H6···H4^xiii	2.866
C14···C13^ix	3.4829 (19)	H6···H5^xiii	2.690
C14···C14^x	3.3194 (19)	H6···H9^v	3.346
C14···C15^x	3.5954 (19)	H6···H14^vii	2.996
C14···C16^ix	3.592 (2)	H6···H15^vii	3.038
C15···O1^vi	3.5549 (14)	H6···H16^vii	3.211
C15···C14^x	3.5954 (19)	H7···O2^i	3.123
C15···C16^ix	3.544 (2)	H7···O3^i	2.864
C16···C8^xi	3.525 (2)	H7···C16^vii	3.255
C16···C14^ix	3.592 (2)	H7···H1^i	2.743
C16···C15^ix	3.544 (2)	H7···H2^iii	2.948
O1···H3^i	3.343	H7···H10^xii	3.377
O1···H9	1.89 (2)	H7···H11^xii	3.178
O1···H11^ii	2.563	H7···H14^vii	3.325
O1···H13^iii	2.902	H7···H15^vii	3.143
O1···H14^ii	2.933	H7···H16^vii	2.779
O2···H4^v	3.447	H8···O3^v	3.577
O2···H4^vi	2.600	H8···O4^v	2.858
O2···H6^i	3.471	H8···C10^v	3.264
O2···H7^v	3.123	H8···C11^xii	3.359
O2···H9	3.29 (2)	H8···C12^xii	3.193
O3···H1	1.93 (2)	H8···C16^vii	3.482
O3···H2^iv	3.312	H8···H9^v	2.809
O3···H5^vi	2.772	H8···H10^xii	3.120
O3···H6^i	3.206	H8···H11^xii	2.849
O3···H7^v	2.864	H8···H15^vii	2.949
O3···H8^i	3.577	H8···H16^vii	3.349
O3···H10^ii	3.255	H9···O1	1.89 (2)
O3···H11^ii	3.581	H9···O2	3.29 (2)
O3···H16^x	3.053	H9···C1	3.05 (2)
O4···H1	3.30 (2)	H9···C8^i	3.43 (2)
O4···H3^i	3.576	H9···C11^ii	3.60 (2)
O4···H8^i	2.858	H9···C12^ii	3.32 (2)
O4···H10^ii	3.152	H9···H1	2.39 (2)
O4···H11^ii	3.024	H9···H3^i	3.382
O4···H12^iii	2.388	H9···H6^i	3.346
O4···H13^iii	3.274	H9···H8^i	2.809
C1···H3^i	3.553	H9···H10^ii	3.215
C1···H9	3.05 (2)	H9···H11^ii	2.705
C1···H11^ii	3.530	H9···H12^iii	2.917
C1···H13^iii	3.471	H9···H13^iii	3.262
C1···H14^ii	3.347	H10···O3^viii	3.255
C2···H4^vi	3.598	H10···O4^viii	3.152
C3···H5^v	3.527	H10···C9^viii	3.027
C3···H14^xii	3.460	H10···C10^viii	2.923
C3···H16^xii	3.510	H10···C11^viii	3.473
C4···H11^xii	3.335	H10···C16^iii	3.561
C4···H13^iv	3.487	H10···H7^xiv	3.377
C4···H14^xii	3.297	H10···H8^xiv	3.120
C4···H16^xii	3.488	H10···H9^viii	3.215
C6···H2^i	3.576	H10···H12^iii	2.955
C6···H4^xiii	3.341	H10···H15^iii	3.090
C6···H6^xiii	3.348	H10···H16^iii	3.195
C7···H2^i	3.288	H11···O1^viii	2.563
C7···H6^xiii	3.270	H11···O3^viii	3.581
C7···H13^iii	3.321	H11···O4^viii	3.024
C7···H14^ii	3.230	H11···C1^viii	3.530
C8···H1^i	3.53 (2)	H11···C4^xiv	3.335
C8···H2^iii	3.587	H11···C8^xiv	3.343
C8···H9^v	3.43 (2)	H11···H1^viii	3.567
C8···H11^xii	3.343	H11···H3^xiv	2.716
C8···H14^vii	3.492	H11···H7^xiv	3.178
C8···H15^vii	3.224	H11···H8^xiv	2.849
C8···H16^vii	3.285	H11···H9^viii	2.705
C9···H1	3.12 (2)	H11···H12^ix	3.427
C9···H5^vi	3.139	H12···O4^vi	2.388
C9···H6^i	3.509	H12···C10^vi	3.401
C9···H10^ii	3.027	H12···C11^vi	3.572
C9···H14^ix	3.586	H12···C12^ix	3.409
C9···H15^ix	3.095	H12···C14^x	3.304
C9···H16^x	3.108	H12···C15^x	3.429
C10···H8^i	3.264	H12···H9^vi	2.917
C10···H10^ii	2.923	H12···H10^vi	2.955
C10···H12^iii	3.401	H12···H11^ix	3.427
C10···H15^ix	3.054	H12···H12^x	3.553
C11···H8^xiv	3.359	H13···O1^vi	2.902
C11···H9^viii	3.60 (2)	H13···O4^vi	3.274
C11···H10^ii	3.473	H13···C1^vi	3.471
C11···H12^iii	3.572	H13···C4^iv	3.487
C11···H15^ix	3.157	H13···C7^vi	3.321
C12···H3^xiv	3.135	H13···C13^x	3.473
C12···H8^xiv	3.193	H13···C16^x	3.338
C12···H9^viii	3.32 (2)	H13···H2^iv	3.233
C12···H12^ix	3.409	H13···H3^iv	2.789
C12···H15^ix	3.298	H13···H5^vi	2.640
C13···H3^xiv	3.317	H13···H9^vi	3.262
C13···H13^x	3.473	H13···H14^ix	3.374
C13···H15^ix	3.362	H13···H16^x	2.546
C14···H12^x	3.304	H14···O1^viii	2.933
C14···H14^ix	3.525	H14···C1^viii	3.347
C14···H15^ix	3.223	H14···C3^xiv	3.460
C15···H5^vi	3.100	H14···C4^xiv	3.297
C15···H12^x	3.429	H14···C7^viii	3.230
C15···H14^ix	3.257	H14···C8^xi	3.492
C15···H15^ix	3.102	H14···C9^ix	3.586
C15···H16^x	2.842	H14···C14^ix	3.525
C16···H2^xiv	3.400	H14···C15^ix	3.257
C16···H3^xiv	3.082	H14···H2^xiv	3.072
C16···H5^viii	3.537	H14···H3^xiv	2.784
C16···H6^xi	3.263	H14···H5^viii	2.703
C16···H7^xi	3.255	H14···H6^xi	2.996
C16···H8^xi	3.482	H14···H7^xi	3.325
C16···H10^vi	3.561	H14···H13^ix	3.374
C16···H13^x	3.338	H15···C8^xi	3.224
H1···O3	1.93 (2)	H15···C9^ix	3.095
H1···O4	3.30 (2)	H15···C10^ix	3.054
H1···C8^v	3.53 (2)	H15···C11^ix	3.157
H1···C9	3.12 (2)	H15···C12^ix	3.298
H1···H4^vi	3.030	H15···C13^ix	3.362
H1···H5^vi	3.448	H15···C14^ix	3.223
H1···H6^i	3.227	H15···C15^ix	3.102
H1···H7^v	2.743	H15···H5^viii	3.597
H1···H9	2.39 (2)	H15···H6^xi	3.038
H1···H11^ii	3.567	H15···H7^xi	3.143
H2···O3^iv	3.312	H15···H8^xi	2.949
H2···C6^v	3.576	H15···H10^vi	3.090
H2···C7^v	3.288	H16···O3^x	3.053
H2···C8^vi	3.587	H16···C3^xiv	3.510
H2···C16^xii	3.400	H16···C4^xiv	3.488
H2···H4^vi	3.450	H16···C8^xi	3.285
H2···H5^v	3.223	H16···C9^x	3.108
H2···H6^vi	3.366	H16···C15^x	2.842
H2···H7^vi	2.948	H16···H2^xiv	2.844
H2···H13^iv	3.233	H16···H3^xiv	2.806
H2···H14^xii	3.072	H16···H6^xi	3.211
H2···H16^xii	2.844	H16···H7^xi	2.779
H3···O1^v	3.343	H16···H8^xi	3.349
H3···O4^v	3.576	H16···H10^vi	3.195
H3···C1^v	3.553	H16···H13^x	2.546
H3···C12^xii	3.135
O1—C1—C2	117.08 (13)	C2—C3—H2	114.7
O1—C1—C7	120.26 (11)	C4—C3—H2	114.6
C2—C1—C7	122.65 (12)	C3—C4—H3	114.7
O2—C2—C1	114.58 (12)	C5—C4—H3	114.7
O2—C2—C3	116.73 (11)	C5—C6—H4	114.4
C1—C2—C3	128.68 (14)	C7—C6—H4	114.3
C2—C3—C4	130.70 (12)	C1—C7—H5	113.7
C3—C4—C5	130.60 (12)	C6—C7—H5	114.4
C4—C5—C6	124.12 (15)	C5—C8—H6	109.7
C4—C5—C8	119.37 (12)	C5—C8—H7	109.2
C6—C5—C8	116.50 (12)	C5—C8—H8	109.5
C5—C6—C7	131.27 (14)	H6—C8—H7	109.5
C1—C7—C6	131.89 (11)	H6—C8—H8	109.5
O3—C9—C10	117.29 (13)	H7—C8—H8	109.5
O3—C9—C15	120.51 (10)	C10—C11—H10	114.0
C10—C9—C15	122.18 (12)	C12—C11—H10	114.6
O4—C10—C9	114.66 (11)	C11—C12—H11	115.3
O4—C10—C11	116.60 (11)	C13—C12—H11	115.0
C9—C10—C11	128.73 (14)	C13—C14—H12	114.0
C10—C11—C12	131.32 (12)	C15—C14—H12	114.4
C11—C12—C13	129.69 (12)	C9—C15—H13	113.6
C12—C13—C14	124.45 (14)	C14—C15—H13	114.5
C12—C13—C16	119.42 (11)	C13—C16—H14	109.4
C14—C13—C16	116.11 (12)	C13—C16—H15	109.5
C13—C14—C15	131.62 (13)	C13—C16—H16	109.5
C9—C15—C14	131.83 (10)	H14—C16—H15	109.5
C2—O2—H1	109.4 (14)	H14—C16—H16	109.5
C10—O4—H9	110.9 (14)	H15—C16—H16	109.5
O1—C1—C2—O2	1.19 (17)	O3—C9—C10—O4	2.94 (17)
O1—C1—C2—C3	−177.96 (13)	O3—C9—C10—C11	−176.20 (13)
O1—C1—C7—C6	179.68 (14)	O3—C9—C15—C14	176.88 (14)
C2—C1—C7—C6	−1.5 (2)	C10—C9—C15—C14	−4.5 (2)
C7—C1—C2—O2	−177.69 (12)	C15—C9—C10—O4	−175.71 (12)
C7—C1—C2—C3	3.2 (2)	C15—C9—C10—C11	5.2 (2)
O2—C2—C3—C4	179.56 (13)	O4—C10—C11—C12	178.27 (13)
C1—C2—C3—C4	−1.3 (2)	C9—C10—C11—C12	−2.6 (2)
C2—C3—C4—C5	−1.6 (2)	C10—C11—C12—C13	0.3 (2)
C3—C4—C5—C6	1.1 (2)	C11—C12—C13—C14	−1.0 (2)
C3—C4—C5—C8	−178.03 (14)	C11—C12—C13—C16	−179.76 (13)
C4—C5—C6—C7	1.4 (2)	C12—C13—C14—C15	2.0 (2)
C8—C5—C6—C7	−179.44 (14)	C16—C13—C14—C15	−179.27 (14)
C5—C6—C7—C1	−1.4 (2)	C13—C14—C15—C9	0.7 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1	0.97 (2)	2.04 (2)	2.5877 (12)	113.7 (19)
O2—H1···O3	0.97 (2)	1.93 (2)	2.7606 (15)	142.3 (19)
O4—H9···O1	0.94 (2)	1.89 (2)	2.6976 (15)	142.4 (19)
O4—H9···O3	0.94 (2)	2.09 (2)	2.5989 (12)	112.6 (19)
C6—H4···O2^iii	0.95	2.60	3.4528 (17)	150
C12—H11···O1^viii	0.95	2.56	3.4369 (16)	153
C14—H12···O4^vi	0.95	2.39	3.2589 (15)	152

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