3-[(1Z)-1-Hydr­oxy-3-oxobut-1-en-1-yl]-7-methyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione

The mol­ecular structure of the title compound, C₁₃H₁₀O₆, contains a cis-enol ring disordered with respect to the position of the hydroxyl proton. The crystal structure contains sheets perpendicular to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.086
• Data-to-parameter ratio = 25.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT432_ALERT_2_C Short Inter X...Y Contact  C11    ..  C11     ..       3.11 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker–Nonius, 2004); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

3-[(1Z)-1-Hydroxy-3-oxobut-1-en-1-yl]-7-methyl-2H,5H-pyrano[4,3-b]pyran- 2,5-dione

Crystal data

C13H10O6	F(000) = 544
Mr = 262.22	Dx = 1.541 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1339 reflections
a = 8.8290 (4) Å	θ = 2.7–27.4°
b = 14.1820 (5) Å	µ = 0.12 mm^−1
c = 12.5238 (5) Å	T = 120 K
β = 133.882 (2)°	Needle, orange
V = 1130.27 (9) Å^3	0.30 × 0.05 × 0.05 mm
Z = 4

Data collection

Bruker APEX 2 diffractometer	θmax = 33.2°, θmin = 2.7°
Graphite monochromator	h = −13→13
ω scans	k = −21→21
26469 measured reflections	l = −19→19
4322 independent reflections	Standard reflections: 2 frames; every 30 frames reflections
2755 reflections with I > 2σ(I)	intensity decay: none
Rint = 0.037

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters not refined
wR(F^2) = 0.086	w = [1-(Fo-Fc)^2/36σ^2(F)]^2/[10.2T0(x) + 13.2T1(x) + 3.67T2(x)] where Ti are Chebychev polynomials and x = Fc/Fmax (Prince, 1982; Watkin, 1994)
S = 1.02	(Δ/σ)max = 0.000399
4313 reflections	Δρmax = 0.46 e Å^−3
172 parameters	Δρmin = −0.31 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O7	0.79440 (13)	0.62414 (6)	0.53663 (10)	0.0210
O8	0.58867 (14)	0.75056 (6)	0.43741 (10)	0.0203
O12	−0.11867 (14)	0.45714 (7)	0.05620 (11)	0.0253
O13	0.05558 (13)	0.59101 (6)	0.15699 (10)	0.0200
O15	0.47183 (14)	0.31040 (6)	0.34851 (10)	0.0229
O18	0.34050 (14)	0.14776 (7)	0.27558 (10)	0.0238
C1	0.4089 (2)	0.89602 (9)	0.36101 (16)	0.0262
C2	0.3946 (2)	0.79184 (8)	0.34339 (14)	0.0201
C3	0.21518 (19)	0.74086 (8)	0.24894 (14)	0.0204
C4	0.23446 (18)	0.64165 (8)	0.25011 (13)	0.0175
C5	0.42705 (17)	0.59794 (8)	0.34332 (12)	0.0166
C6	0.61611 (18)	0.65377 (8)	0.44525 (12)	0.0175
C9	0.43585 (18)	0.49846 (8)	0.33951 (13)	0.0175
C10	0.25782 (17)	0.44512 (8)	0.24629 (12)	0.0164
C11	0.05309 (18)	0.49158 (8)	0.14673 (13)	0.0186
C14	0.27925 (18)	0.34116 (8)	0.25091 (13)	0.0183
C16	0.11082 (18)	0.27810 (8)	0.16209 (13)	0.0191
C17	0.15138 (19)	0.18065 (9)	0.17996 (13)	0.0195
C19	−0.0231 (2)	0.11072 (9)	0.08729 (15)	0.0242
H20	0.2718	0.9233	0.2847	0.0378*
H21	0.5027	0.9205	0.3540	0.0378*
H22	0.4606	0.9116	0.4563	0.0378*
H23	0.0831	0.7696	0.1857	0.0234*
H24	0.5660	0.4683	0.4018	0.0192*
H25	−0.0221	0.3004	0.0950	0.0218*
H26	−0.1493	0.1375	0.0390	0.0349*
H27	−0.0275	0.0879	0.0157	0.0349*
H28	0.0007	0.0579	0.1465	0.0349*
H29	0.4622	0.2450	0.3421	0.0263*	0.5000
H30	0.4250	0.2109	0.3211	0.0275*	0.5000

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0156 (4)	0.0207 (4)	0.0219 (4)	−0.0009 (3)	0.0111 (3)	−0.0013 (3)
O8	0.0200 (4)	0.0165 (4)	0.0233 (4)	−0.0008 (3)	0.0146 (3)	−0.0006 (3)
O12	0.0153 (4)	0.0247 (4)	0.0271 (4)	−0.0012 (3)	0.0114 (4)	−0.0015 (4)
O13	0.0156 (3)	0.0189 (4)	0.0211 (4)	0.0013 (3)	0.0111 (3)	0.0010 (3)
O15	0.0163 (4)	0.0185 (4)	0.0232 (4)	0.0006 (3)	0.0097 (3)	−0.0005 (3)
O18	0.0206 (4)	0.0209 (4)	0.0229 (4)	0.0013 (3)	0.0125 (4)	−0.0004 (3)
C1	0.0322 (6)	0.0169 (5)	0.0308 (6)	0.0023 (5)	0.0223 (6)	0.0009 (5)
C2	0.0235 (5)	0.0175 (5)	0.0230 (5)	0.0025 (4)	0.0175 (5)	0.0023 (4)
C3	0.0202 (5)	0.0177 (5)	0.0227 (5)	0.0031 (4)	0.0146 (4)	0.0021 (4)
C4	0.0171 (4)	0.0183 (5)	0.0181 (4)	0.0010 (4)	0.0126 (4)	0.0012 (4)
C5	0.0156 (4)	0.0169 (4)	0.0167 (4)	0.0008 (4)	0.0110 (4)	0.0006 (4)
C6	0.0176 (4)	0.0174 (5)	0.0183 (4)	−0.0011 (4)	0.0128 (4)	−0.0009 (4)
C9	0.0157 (4)	0.0181 (5)	0.0172 (4)	0.0010 (4)	0.0108 (4)	0.0002 (4)
C10	0.0148 (4)	0.0173 (4)	0.0156 (4)	0.0004 (3)	0.0100 (4)	0.0004 (3)
C11	0.0167 (4)	0.0203 (5)	0.0190 (5)	0.0009 (4)	0.0125 (4)	0.0009 (4)
C14	0.0183 (5)	0.0180 (5)	0.0179 (4)	−0.0005 (4)	0.0122 (4)	−0.0009 (4)
C16	0.0159 (4)	0.0184 (5)	0.0194 (5)	−0.0014 (4)	0.0109 (4)	−0.0015 (4)
C17	0.0196 (5)	0.0202 (5)	0.0191 (5)	−0.0019 (4)	0.0136 (4)	−0.0021 (4)
C19	0.0222 (5)	0.0194 (5)	0.0285 (6)	−0.0046 (4)	0.0166 (5)	−0.0046 (4)

Geometric parameters (Å, º)

O7—C6	1.2111 (14)	C3—H23	0.94
O8—C2	1.3670 (15)	C4—C5	1.3735 (15)
O8—C6	1.3855 (14)	C5—C6	1.4452 (16)
O12—C11	1.2001 (14)	C5—C9	1.4155 (16)
O13—C4	1.3478 (14)	C9—C10	1.3645 (15)
O13—C11	1.4147 (15)	C9—H24	0.93
O15—C14	1.3016 (14)	C10—C11	1.4600 (16)
O15—H29	0.93	C10—C14	1.4824 (16)
O18—C17	1.2913 (15)	C14—C16	1.3983 (16)
O18—H30	1.05	C16—C17	1.4062 (17)
C1—C2	1.4863 (17)	C16—H25	0.90
C1—H20	0.96	C17—C19	1.4915 (17)
C1—H21	0.96	C19—H26	0.90
C1—H22	0.96	C19—H27	0.93
C2—C3	1.3539 (17)	C19—H28	0.97
C3—C4	1.4162 (16)
C2—O8—C6	122.59 (10)	C5—C9—H24	119.6
C4—O13—C11	123.01 (9)	C10—C9—H24	118.8
C14—O15—H29	105.7	C9—C10—C11	119.37 (10)
C17—O18—H30	99.9	C9—C10—C14	118.54 (10)
C2—C1—H20	109.5	C11—C10—C14	122.09 (10)
C2—C1—H21	109.7	C10—C11—O13	116.12 (10)
H20—C1—H21	109.6	C10—C11—O12	128.96 (12)
C2—C1—H22	109.3	O13—C11—O12	114.92 (11)
H20—C1—H22	109.1	C10—C14—O15	114.73 (10)
H21—C1—H22	109.5	C10—C14—C16	124.64 (11)
C1—C2—O8	111.78 (11)	O15—C14—C16	120.62 (11)
C1—C2—C3	126.02 (12)	C14—C16—C17	119.27 (11)
O8—C2—C3	122.19 (11)	C14—C16—H25	119.7
C2—C3—C4	117.52 (11)	C17—C16—H25	121.1
C2—C3—H23	121.6	C16—C17—O18	121.71 (11)
C4—C3—H23	120.9	C16—C17—C19	121.19 (11)
C3—C4—O13	117.39 (10)	O18—C17—C19	117.09 (11)
C3—C4—C5	121.76 (11)	C17—C19—H26	111.8
O13—C4—C5	120.85 (11)	C17—C19—H27	108.2
C4—C5—C6	119.66 (10)	H26—C19—H27	107.0
C4—C5—C9	119.06 (11)	C17—C19—H28	111.1
C6—C5—C9	121.27 (10)	H26—C19—H28	110.5
C5—C6—O8	116.23 (10)	H27—C19—H28	108.1
C5—C6—O7	126.40 (11)	O15—H29—H30	157.6
O8—C6—O7	117.36 (10)	O18—H30—H29	175.0
C5—C9—C10	121.59 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O15—H29···O18	0.93	1.58	2.456 (2)	154
O18—H30···O15	1.05	1.44	2.456 (2)	161
C3—H23···O7^i	0.93	2.38	3.2928 (19)	166
C19—H26···O15^ii	0.90	2.52	3.405 (2)	165

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