2,2-Dimethyl-5-(2-nitro-benzyl-idene)-1,3-dioxane-4,6-dione.

The asymmetric unit of the title compound, C13H11NO6, contains two mol-ecules in both of which the six-membered 1,3-dioxane-4,6-dione ring shows a screw-boat conformation. The dihedral angles between the best planes through the six-membered rings are 47.8 (2) and 49.8 (2)°. In the crystal, C-H⋯O inter-actions link the mol-ecules, building a supramolecular sheet parallel to the c axis.

Related literature

For general applications of Meldrum’s acid, see: Palasz et al. (2007 ▶); Fillion et al. (2006 ▶); Mizukami et al. (1993 ▶). For the synthesis of heterocyclic compounds, see: Scott & Raston (2000 ▶); Alvim et al. (2005 ▶); Fillion & Dumas (2008 ▶). For combinatorial synthesis, see: Shaabani et al. (2004 ▶); Wang et al. (2007 ▶); Cochard et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For NMR data, see: Bigi et al. (2001 ▶).

Experimental

Crystal data

C13H11NO6

M = 277.23

Triclinic,

a = 10.0240 (4) Å

b = 10.4830 (5) Å

c = 12.4076 (5) Å

α = 105.385 (4)°

β = 94.669 (3)°

γ = 93.096 (3)°

V = 1249.03 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 130 K

0.39 × 0.22 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.968, T max = 0.985

8703 measured reflections

4526 independent reflections

3902 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.03

4526 reflections

365 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049677/bt6875sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049677/bt6875Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049677/bt6875Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H11NO6	Z = 4
Mr = 277.23	F(000) = 576
Triclinic, P1	Dx = 1.474 Mg m−3
a = 10.0240 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4830 (5) Å	Cell parameters from 5470 reflections
c = 12.4076 (5) Å	θ = 3.4–25.2°
α = 105.385 (4)°	µ = 0.12 mm−1
β = 94.669 (3)°	T = 130 K
γ = 93.096 (3)°	Prism, colorless
V = 1249.03 (10) Å3	0.39 × 0.22 × 0.14 mm

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	4526 independent reflections
Graphite monochromator	3902 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.018
ω scans	θmax = 25.3°, θmin = 3.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −12→12
Tmin = 0.968, Tmax = 0.985	k = −10→12
8703 measured reflections	l = −13→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.3347P] where P = (Fo2 + 2Fc2)/3
4526 reflections	(Δ/σ)max < 0.001
365 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
O1	0.61144 (10)	0.10481 (11)	0.54216 (9)	0.0347 (3)
O2	0.53572 (11)	0.09437 (10)	0.69780 (9)	0.0351 (3)
O6	0.23911 (10)	0.16149 (11)	0.32752 (8)	0.0334 (3)
O5	0.68803 (9)	0.16562 (11)	0.25320 (8)	0.0293 (2)
O3	0.29864 (9)	0.16222 (10)	0.16040 (8)	0.0260 (2)
O4	0.52511 (9)	0.16412 (10)	0.12250 (8)	0.0255 (2)
N1	0.54108 (11)	0.14413 (11)	0.61912 (10)	0.0241 (3)
C2	0.44468 (13)	0.30112 (13)	0.52086 (11)	0.0203 (3)
C1	0.46117 (13)	0.25651 (13)	0.61755 (11)	0.0203 (3)
C13	0.40048 (14)	0.31165 (14)	0.71352 (11)	0.0240 (3)
H8	0.4137	0.2793	0.7762	0.029*
C12	0.32022 (14)	0.41500 (14)	0.71558 (12)	0.0264 (3)
H9	0.2803	0.4543	0.7801	0.032*
C11	0.29991 (14)	0.45936 (14)	0.62034 (12)	0.0263 (3)
H10	0.2446	0.5279	0.6207	0.032*
C10	0.36058 (13)	0.40341 (14)	0.52468 (12)	0.0243 (3)
H11	0.345	0.4347	0.4616	0.029*
C3	0.51994 (13)	0.25533 (13)	0.42226 (11)	0.0215 (3)
H7	0.6126	0.2577	0.4371	0.026*
C4	0.47179 (13)	0.21081 (13)	0.31422 (11)	0.0209 (3)
C5	0.32781 (14)	0.17904 (14)	0.27213 (12)	0.0241 (3)
C7	0.57212 (13)	0.18052 (14)	0.23029 (11)	0.0222 (3)
C6	0.39619 (13)	0.21135 (15)	0.09837 (12)	0.0243 (3)
C8	0.35526 (15)	0.14531 (17)	−0.02350 (12)	0.0330 (4)
H1	0.2719	0.1764	−0.0458	0.05*
H2	0.3444	0.0509	−0.0351	0.05*
H3	0.4233	0.1663	−0.0676	0.05*
C9	0.40534 (15)	0.36051 (15)	0.12822 (13)	0.0302 (3)
H4	0.3197	0.3899	0.1091	0.045*
H5	0.4716	0.3912	0.0872	0.045*
H6	0.4306	0.3957	0.2074	0.045*
O7	0.21049 (10)	0.63351 (11)	0.34639 (9)	0.0367 (3)
O8	0.12315 (15)	0.64061 (17)	0.49838 (11)	0.0703 (5)
O11	−0.11562 (10)	0.62735 (10)	0.09585 (9)	0.0305 (2)
O12	0.33877 (10)	0.68213 (12)	0.06066 (9)	0.0380 (3)
O10	−0.04438 (9)	0.64388 (9)	−0.06351 (8)	0.0235 (2)
O9	0.18763 (9)	0.66645 (9)	−0.08312 (8)	0.0230 (2)
N2	0.12876 (12)	0.67424 (13)	0.41284 (10)	0.0297 (3)
C15	0.04065 (13)	0.81061 (14)	0.29236 (11)	0.0236 (3)
C23	−0.05066 (14)	0.90041 (15)	0.27642 (12)	0.0282 (3)
H22	−0.0497	0.9318	0.2131	0.034*
C24	−0.14323 (14)	0.94452 (15)	0.35226 (13)	0.0291 (3)
H21	−0.2031	1.0049	0.3395	0.035*
C25	−0.14677 (14)	0.89901 (14)	0.44700 (12)	0.0267 (3)
H20	−0.2091	0.9285	0.4978	0.032*
C26	−0.05768 (14)	0.80991 (14)	0.46575 (11)	0.0246 (3)
H19	−0.0596	0.7782	0.5289	0.029*
C14	0.03491 (13)	0.76803 (13)	0.38935 (11)	0.0218 (3)
C16	0.14020 (14)	0.77088 (15)	0.21051 (12)	0.0263 (3)
H18	0.2304	0.7894	0.2375	0.032*
C17	0.11190 (13)	0.71080 (14)	0.10134 (12)	0.0232 (3)
C18	0.22400 (14)	0.68726 (14)	0.02790 (12)	0.0256 (3)
C20	−0.02527 (13)	0.65966 (13)	0.04834 (11)	0.0220 (3)
C19	0.05674 (13)	0.70168 (14)	−0.11726 (11)	0.0223 (3)
C21	0.05316 (14)	0.85027 (14)	−0.08805 (12)	0.0265 (3)
H12	−0.0339	0.8722	−0.1125	0.04*
H13	0.1202	0.8868	−0.1249	0.04*
H14	0.0709	0.8865	−0.0082	0.04*
C22	0.02837 (15)	0.63545 (16)	−0.24028 (12)	0.0321 (4)
H15	−0.0618	0.6486	−0.2651	0.048*
H16	0.0385	0.5421	−0.2539	0.048*
H17	0.0902	0.6731	−0.2808	0.048*

	U11	U22	U33	U12	U13	U23
O1	0.0352 (6)	0.0324 (6)	0.0391 (6)	0.0151 (5)	0.0113 (5)	0.0096 (5)
O2	0.0461 (7)	0.0304 (6)	0.0325 (6)	0.0077 (5)	−0.0012 (5)	0.0158 (5)
O6	0.0196 (5)	0.0511 (7)	0.0312 (6)	0.0000 (5)	0.0079 (4)	0.0131 (5)
O5	0.0189 (5)	0.0423 (6)	0.0304 (6)	0.0084 (5)	0.0056 (4)	0.0143 (5)
O3	0.0199 (5)	0.0345 (6)	0.0234 (5)	−0.0002 (4)	0.0016 (4)	0.0084 (4)
O4	0.0213 (5)	0.0358 (6)	0.0218 (5)	0.0085 (4)	0.0049 (4)	0.0097 (4)
N1	0.0233 (6)	0.0215 (6)	0.0259 (7)	0.0011 (5)	−0.0038 (5)	0.0056 (5)
C2	0.0161 (6)	0.0212 (7)	0.0232 (7)	−0.0007 (5)	0.0007 (5)	0.0059 (6)
C1	0.0171 (7)	0.0173 (7)	0.0252 (7)	−0.0004 (5)	−0.0016 (5)	0.0050 (5)
C13	0.0264 (7)	0.0248 (7)	0.0208 (7)	−0.0013 (6)	0.0008 (6)	0.0072 (6)
C12	0.0267 (8)	0.0246 (7)	0.0262 (8)	0.0015 (6)	0.0084 (6)	0.0026 (6)
C11	0.0238 (7)	0.0232 (7)	0.0332 (8)	0.0067 (6)	0.0070 (6)	0.0075 (6)
C10	0.0226 (7)	0.0270 (8)	0.0264 (8)	0.0038 (6)	0.0034 (6)	0.0121 (6)
C3	0.0171 (7)	0.0225 (7)	0.0274 (8)	0.0032 (6)	0.0035 (5)	0.0105 (6)
C4	0.0188 (7)	0.0222 (7)	0.0244 (7)	0.0039 (6)	0.0047 (5)	0.0098 (6)
C5	0.0212 (7)	0.0260 (8)	0.0259 (8)	0.0044 (6)	0.0037 (6)	0.0076 (6)
C7	0.0219 (7)	0.0232 (7)	0.0231 (7)	0.0028 (6)	0.0042 (6)	0.0084 (6)
C6	0.0164 (7)	0.0332 (8)	0.0259 (8)	0.0042 (6)	0.0038 (5)	0.0116 (6)
C8	0.0300 (8)	0.0439 (10)	0.0249 (8)	0.0053 (7)	0.0005 (6)	0.0091 (7)
C9	0.0273 (8)	0.0311 (8)	0.0343 (9)	0.0036 (7)	0.0014 (6)	0.0126 (7)
O7	0.0308 (6)	0.0402 (7)	0.0411 (7)	0.0121 (5)	0.0056 (5)	0.0124 (5)
O8	0.0808 (10)	0.1092 (13)	0.0500 (9)	0.0550 (10)	0.0230 (7)	0.0579 (9)
O11	0.0240 (5)	0.0348 (6)	0.0374 (6)	−0.0012 (5)	0.0082 (4)	0.0173 (5)
O12	0.0183 (5)	0.0609 (8)	0.0386 (6)	0.0095 (5)	0.0038 (4)	0.0185 (6)
O10	0.0185 (5)	0.0263 (5)	0.0243 (5)	−0.0002 (4)	0.0039 (4)	0.0045 (4)
O9	0.0186 (5)	0.0264 (5)	0.0246 (5)	0.0066 (4)	0.0055 (4)	0.0061 (4)
N2	0.0281 (7)	0.0360 (7)	0.0262 (7)	0.0032 (6)	−0.0032 (5)	0.0120 (6)
C15	0.0199 (7)	0.0275 (8)	0.0230 (7)	−0.0015 (6)	−0.0011 (5)	0.0077 (6)
C23	0.0289 (8)	0.0315 (8)	0.0282 (8)	0.0021 (6)	0.0000 (6)	0.0158 (6)
C24	0.0250 (8)	0.0255 (8)	0.0363 (9)	0.0039 (6)	−0.0005 (6)	0.0080 (6)
C25	0.0214 (7)	0.0265 (8)	0.0289 (8)	−0.0022 (6)	0.0031 (6)	0.0023 (6)
C26	0.0245 (7)	0.0282 (8)	0.0202 (7)	−0.0054 (6)	−0.0004 (5)	0.0074 (6)
C14	0.0192 (7)	0.0234 (7)	0.0220 (7)	−0.0007 (6)	−0.0044 (5)	0.0069 (6)
C16	0.0203 (7)	0.0346 (8)	0.0275 (8)	0.0028 (6)	0.0009 (6)	0.0149 (6)
C17	0.0190 (7)	0.0266 (7)	0.0279 (8)	0.0044 (6)	0.0049 (6)	0.0131 (6)
C18	0.0215 (8)	0.0282 (8)	0.0293 (8)	0.0037 (6)	0.0048 (6)	0.0103 (6)
C20	0.0217 (7)	0.0189 (7)	0.0276 (8)	0.0058 (6)	0.0051 (6)	0.0084 (6)
C19	0.0163 (7)	0.0279 (8)	0.0239 (7)	0.0040 (6)	0.0054 (5)	0.0078 (6)
C21	0.0263 (8)	0.0278 (8)	0.0285 (8)	0.0071 (6)	0.0073 (6)	0.0106 (6)
C22	0.0259 (8)	0.0423 (9)	0.0253 (8)	0.0048 (7)	0.0044 (6)	0.0031 (7)

O1—N1	1.2293 (15)	O7—N2	1.2223 (15)
O2—N1	1.2263 (15)	O8—N2	1.2083 (16)
O6—C5	1.2024 (16)	O11—C20	1.2009 (16)
O5—C7	1.2018 (16)	O12—C18	1.1974 (17)
O3—C5	1.3554 (17)	O10—C20	1.3497 (16)
O3—C6	1.4464 (16)	O10—C19	1.4482 (16)
O4—C7	1.3442 (16)	O9—C18	1.3521 (17)
O4—C6	1.4455 (16)	O9—C19	1.4430 (16)
N1—C1	1.4634 (17)	N2—C14	1.4642 (18)
C2—C10	1.3928 (19)	C15—C23	1.388 (2)
C2—C1	1.3996 (19)	C15—C14	1.3944 (19)
C2—C3	1.4745 (18)	C15—C16	1.4785 (19)
C1—C13	1.3830 (19)	C23—C24	1.385 (2)
C13—C12	1.380 (2)	C23—H22	0.93
C13—H8	0.93	C24—C25	1.383 (2)
C12—C11	1.385 (2)	C24—H21	0.93
C12—H9	0.93	C25—C26	1.377 (2)
C11—C10	1.3818 (19)	C25—H20	0.93
C11—H10	0.93	C26—C14	1.3853 (19)
C10—H11	0.93	C26—H19	0.93
C3—C4	1.3364 (19)	C16—C17	1.333 (2)
C3—H7	0.93	C16—H18	0.93
C4—C5	1.4831 (19)	C17—C20	1.4820 (19)
C4—C7	1.4921 (18)	C17—C18	1.4938 (19)
C6—C8	1.499 (2)	C19—C22	1.4961 (19)
C6—C9	1.504 (2)	C19—C21	1.506 (2)
C8—H1	0.96	C21—H12	0.96
C8—H2	0.96	C21—H13	0.96
C8—H3	0.96	C21—H14	0.96
C9—H4	0.96	C22—H15	0.96
C9—H5	0.96	C22—H16	0.96
C9—H6	0.96	C22—H17	0.96
C5—O3—C6	119.09 (10)	C20—O10—C19	118.89 (10)
C7—O4—C6	118.75 (10)	C18—O9—C19	118.26 (10)
O2—N1—O1	123.04 (12)	O8—N2—O7	122.23 (13)
O2—N1—C1	118.41 (11)	O8—N2—C14	118.42 (12)
O1—N1—C1	118.54 (11)	O7—N2—C14	119.35 (12)
C10—C2—C1	116.46 (12)	C23—C15—C14	116.39 (13)
C10—C2—C3	119.36 (12)	C23—C15—C16	119.29 (12)
C1—C2—C3	123.91 (12)	C14—C15—C16	124.26 (13)
C13—C1—C2	122.65 (12)	C24—C23—C15	121.82 (13)
C13—C1—N1	116.92 (12)	C24—C23—H22	119.1
C2—C1—N1	120.40 (12)	C15—C23—H22	119.1
C12—C13—C1	119.50 (13)	C25—C24—C23	120.14 (14)
C12—C13—H8	120.3	C25—C24—H21	119.9
C1—C13—H8	120.3	C23—C24—H21	119.9
C13—C12—C11	119.10 (13)	C26—C25—C24	119.73 (13)
C13—C12—H9	120.5	C26—C25—H20	120.1
C11—C12—H9	120.5	C24—C25—H20	120.1
C10—C11—C12	121.01 (13)	C25—C26—C14	119.18 (13)
C10—C11—H10	119.5	C25—C26—H19	120.4
C12—C11—H10	119.5	C14—C26—H19	120.4
C11—C10—C2	121.25 (13)	C26—C14—C15	122.73 (13)
C11—C10—H11	119.4	C26—C14—N2	117.53 (12)
C2—C10—H11	119.4	C15—C14—N2	119.74 (12)
C4—C3—C2	128.19 (12)	C17—C16—C15	125.68 (13)
C4—C3—H7	115.9	C17—C16—H18	117.2
C2—C3—H7	115.9	C15—C16—H18	117.2
C3—C4—C5	125.32 (12)	C16—C17—C20	123.63 (12)
C3—C4—C7	116.92 (12)	C16—C17—C18	119.06 (12)
C5—C4—C7	117.57 (12)	C20—C17—C18	117.25 (12)
O6—C5—O3	119.04 (12)	O12—C18—O9	120.03 (12)
O6—C5—C4	125.42 (13)	O12—C18—C17	124.61 (13)
O3—C5—C4	115.44 (11)	O9—C18—C17	115.32 (11)
O5—C7—O4	119.64 (12)	O11—C20—O10	119.26 (12)
O5—C7—C4	124.14 (12)	O11—C20—C17	125.36 (13)
O4—C7—C4	116.15 (11)	O10—C20—C17	115.31 (11)
O4—C6—O3	109.08 (10)	O9—C19—O10	109.68 (10)
O4—C6—C8	105.46 (11)	O9—C19—C22	106.65 (11)
O3—C6—C8	106.45 (11)	O10—C19—C22	105.78 (11)
O4—C6—C9	110.69 (11)	O9—C19—C21	110.39 (11)
O3—C6—C9	110.72 (11)	O10—C19—C21	110.60 (11)
C8—C6—C9	114.17 (12)	C22—C19—C21	113.56 (12)
C6—C8—H1	109.5	C19—C21—H12	109.5
C6—C8—H2	109.5	C19—C21—H13	109.5
H1—C8—H2	109.5	H12—C21—H13	109.5
C6—C8—H3	109.5	C19—C21—H14	109.5
H1—C8—H3	109.5	H12—C21—H14	109.5
H2—C8—H3	109.5	H13—C21—H14	109.5
C6—C9—H4	109.5	C19—C22—H15	109.5
C6—C9—H5	109.5	C19—C22—H16	109.5
H4—C9—H5	109.5	H15—C22—H16	109.5
C6—C9—H6	109.5	C19—C22—H17	109.5
H4—C9—H6	109.5	H15—C22—H17	109.5
H5—C9—H6	109.5	H16—C22—H17	109.5
C10—C2—C1—C13	−1.4 (2)	C14—C15—C23—C24	−0.5 (2)
C3—C2—C1—C13	172.63 (13)	C16—C15—C23—C24	−177.84 (13)
C10—C2—C1—N1	176.31 (11)	C15—C23—C24—C25	−0.1 (2)
C3—C2—C1—N1	−9.7 (2)	C23—C24—C25—C26	0.2 (2)
O2—N1—C1—C13	9.41 (18)	C24—C25—C26—C14	0.4 (2)
O1—N1—C1—C13	−169.89 (12)	C25—C26—C14—C15	−1.1 (2)
O2—N1—C1—C2	−168.41 (12)	C25—C26—C14—N2	179.42 (12)
O1—N1—C1—C2	12.29 (18)	C23—C15—C14—C26	1.2 (2)
C2—C1—C13—C12	−0.1 (2)	C16—C15—C14—C26	178.33 (13)
N1—C1—C13—C12	−177.85 (12)	C23—C15—C14—N2	−179.42 (12)
C1—C13—C12—C11	1.4 (2)	C16—C15—C14—N2	−2.2 (2)
C13—C12—C11—C10	−1.2 (2)	O8—N2—C14—C26	−1.8 (2)
C12—C11—C10—C2	−0.3 (2)	O7—N2—C14—C26	178.86 (13)
C1—C2—C10—C11	1.6 (2)	O8—N2—C14—C15	178.79 (15)
C3—C2—C10—C11	−172.72 (13)	O7—N2—C14—C15	−0.60 (19)
C10—C2—C3—C4	−56.1 (2)	C23—C15—C16—C17	−60.5 (2)
C1—C2—C3—C4	130.06 (16)	C14—C15—C16—C17	122.41 (16)
C2—C3—C4—C5	−9.8 (2)	C15—C16—C17—C20	−7.9 (2)
C2—C3—C4—C7	175.41 (13)	C15—C16—C17—C18	174.98 (13)
C6—O3—C5—O6	166.16 (13)	C19—O9—C18—O12	−166.58 (13)
C6—O3—C5—C4	−17.28 (17)	C19—O9—C18—C17	15.59 (17)
C3—C4—C5—O6	−16.9 (2)	C16—C17—C18—O12	22.6 (2)
C7—C4—C5—O6	157.82 (14)	C20—C17—C18—O12	−154.70 (14)
C3—C4—C5—O3	166.76 (13)	C16—C17—C18—O9	−159.71 (13)
C7—C4—C5—O3	−18.49 (18)	C20—C17—C18—O9	23.02 (18)
C6—O4—C7—O5	−165.93 (13)	C19—O10—C20—O11	170.43 (12)
C6—O4—C7—C4	16.79 (17)	C19—O10—C20—C17	−12.53 (17)
C3—C4—C7—O5	16.9 (2)	C16—C17—C20—O11	−24.8 (2)
C5—C4—C7—O5	−158.32 (14)	C18—C17—C20—O11	152.33 (14)
C3—C4—C7—O4	−165.97 (12)	C16—C17—C20—O10	158.34 (13)
C5—C4—C7—O4	18.83 (18)	C18—C17—C20—O10	−24.51 (17)
C7—O4—C6—O3	−50.14 (15)	C18—O9—C19—O10	−50.65 (15)
C7—O4—C6—C8	−164.12 (12)	C18—O9—C19—C22	−164.75 (12)
C7—O4—C6—C9	71.93 (15)	C18—O9—C19—C21	71.46 (14)
C5—O3—C6—O4	50.57 (15)	C20—O10—C19—O9	49.17 (15)
C5—O3—C6—C8	163.91 (12)	C20—O10—C19—C22	163.83 (11)
C5—O3—C6—C9	−71.47 (15)	C20—O10—C19—C21	−72.81 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H7···O5	0.93	2.43	2.7970 (16)	104
C11—H10···O8	0.93	2.45	3.239 (2)	143
C21—H13···O5i	0.96	2.58	3.4188 (17)	145
C16—H18···O12	0.93	2.54	2.8582 (18)	100
C16—H18···O2ii	0.93	2.55	3.4486 (18)	163
C24—H21···O5iii	0.93	2.48	3.3676 (19)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H7⋯O5	0.93	2.43	2.7970 (16)	104
C11—H10⋯O8	0.93	2.45	3.239 (2)	143
C21—H13⋯O5i	0.96	2.58	3.4188 (17)	145
C16—H18⋯O12	0.93	2.54	2.8582 (18)	100
C16—H18⋯O2ii	0.93	2.55	3.4486 (18)	163
C24—H21⋯O5iii	0.93	2.48	3.3676 (19)	160

Symmetry codes: (i) ; (ii) ; (iii) .