cis-1-Ethyl-4,4,6,8-tetra-methyl-2-tosyl-2,3,3a,4,6,7,8,9-octa-hydro-1H-pyrrolo[3',4':3,4]pyrano[6,5-d]pyrimidine-7,9-dione.

In the title compound, C(22)H(29)N(3)O(5)S, the pyrrolidine ring is cis-fused to the dihydro-pyran ring. The pyrrolidine and dihydro-pyran rings adopt twist and half-chair conformations, respectively. The mol-ecule is in a folded conformation; the sulfonyl-bound benzene ring lies over the pyrimidine-dione ring, with a weak π-π inter-action [centroid-centroid distance = 3.6147 (4) Å]. A weak intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked into a three-dimensional network by C-H⋯O hydrogen bonds.

Related literature

For the trans isomer, see: Chinnakali et al. (2007 ▶). For the biological activity of pyran­opyrimidine derivatives, see: Abdel Fattah et al. (2004 ▶); Bedair et al. (2000 ▶, 2001 ▶); Eid et al. (2004 ▶); Shamroukh et al. (2007 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Duax et al. (1976 ▶).

Experimental

Crystal data

C22H29N3O5S

M = 447.54

Monoclinic,

a = 13.2140 (2) Å

b = 9.5681 (2) Å

c = 16.8256 (3) Å

β = 98.946 (1)°

V = 2101.43 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.59 × 0.46 × 0.29 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.864, T max = 0.945

92335 measured reflections

10993 independent reflections

9848 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.105

S = 1.08

10993 reflections

286 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026361/wn2336sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026361/wn2336Isup2.hkl

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

C22H29N3O5S	F(000) = 952
Mr = 447.54	Dx = 1.415 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9302 reflections
a = 13.2140 (2) Å	θ = 2.5–40.9°
b = 9.5681 (2) Å	µ = 0.20 mm−1
c = 16.8256 (3) Å	T = 100 K
β = 98.946 (1)°	Block, colourless
V = 2101.43 (7) Å3	0.59 × 0.46 × 0.29 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	10993 independent reflections
Radiation source: fine-focus sealed tube	9848 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 37.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −22→20
Tmin = 0.864, Tmax = 0.945	k = −16→16
92335 measured reflections	l = −28→28

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.4609P] where P = (Fo2 + 2Fc2)/3
10993 reflections	(Δ/σ)max = 0.002
286 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.583987 (12)	0.842927 (15)	0.406869 (9)	0.01234 (4)
O1	0.65851 (4)	0.94222 (5)	0.38823 (4)	0.01920 (10)
O2	0.54783 (5)	0.84656 (6)	0.48296 (3)	0.01802 (10)
O3	0.48049 (4)	0.66605 (5)	0.12573 (3)	0.01221 (8)
O4	0.56281 (5)	0.22291 (5)	0.20707 (4)	0.01945 (10)
O5	0.34489 (4)	0.46219 (5)	0.34319 (3)	0.01542 (9)
N1	0.48436 (4)	0.86053 (6)	0.33745 (3)	0.01170 (8)
N2	0.52189 (4)	0.44704 (5)	0.16924 (3)	0.01178 (8)
N3	0.45765 (4)	0.34362 (5)	0.27803 (3)	0.01201 (9)
C1	0.50142 (5)	0.87879 (6)	0.25331 (4)	0.01246 (9)
H1A	0.5568	0.8197	0.2414	0.015*
H1B	0.5170	0.9753	0.2425	0.015*
C2	0.39850 (5)	0.83406 (6)	0.20456 (4)	0.01116 (9)
H2	0.3507	0.9129	0.2011	0.013*
C3	0.36105 (4)	0.71839 (6)	0.25639 (3)	0.01025 (9)
H3	0.2865	0.7081	0.2437	0.012*
C4	0.39216 (4)	0.77336 (6)	0.34312 (4)	0.01094 (9)
H4	0.4110	0.6948	0.3798	0.013*
C5	0.40701 (5)	0.78390 (6)	0.11965 (4)	0.01210 (9)
C6	0.46937 (4)	0.56814 (6)	0.18057 (3)	0.01023 (9)
C7	0.41350 (4)	0.58284 (6)	0.24165 (3)	0.01009 (9)
C8	0.63400 (5)	0.67386 (6)	0.39643 (4)	0.01179 (9)
C9	0.60216 (5)	0.56445 (7)	0.44136 (4)	0.01306 (10)
H9	0.5562	0.5809	0.4769	0.016*
C10	0.63973 (5)	0.43040 (7)	0.43263 (4)	0.01394 (10)
H10	0.6177	0.3572	0.4620	0.017*
C11	0.71018 (5)	0.40403 (7)	0.38037 (4)	0.01433 (10)
C12	0.74167 (5)	0.51562 (7)	0.33623 (4)	0.01645 (11)
H12	0.7884	0.4996	0.3012	0.020*
C13	0.70416 (5)	0.64999 (7)	0.34392 (4)	0.01486 (10)
H13	0.7257	0.7233	0.3143	0.018*
C14	0.75187 (6)	0.25884 (7)	0.37293 (5)	0.02037 (12)
H14A	0.7406	0.2040	0.4185	0.031*
H14B	0.8240	0.2640	0.3709	0.031*
H14C	0.7175	0.2160	0.3246	0.031*
C15	0.45325 (6)	0.89403 (7)	0.07111 (4)	0.01763 (11)
H15A	0.4595	0.8570	0.0191	0.026*
H15B	0.5198	0.9198	0.0987	0.026*
H15C	0.4097	0.9749	0.0649	0.026*
C16	0.30475 (5)	0.73203 (7)	0.07499 (4)	0.01565 (10)
H16A	0.3128	0.7040	0.0216	0.023*
H16B	0.2550	0.8057	0.0721	0.023*
H16C	0.2820	0.6537	0.1031	0.023*
C17	0.51744 (5)	0.33126 (6)	0.21815 (4)	0.01279 (9)
C18	0.40139 (5)	0.46334 (6)	0.29140 (4)	0.01094 (9)
C19	0.58284 (6)	0.43377 (7)	0.10385 (4)	0.01794 (12)
H19A	0.5632	0.5055	0.0646	0.027*
H19B	0.5709	0.3437	0.0790	0.027*
H19C	0.6542	0.4433	0.1252	0.027*
C20	0.45052 (6)	0.22000 (7)	0.32843 (4)	0.01626 (11)
H20A	0.5176	0.1809	0.3441	0.024*
H20B	0.4067	0.1518	0.2986	0.024*
H20C	0.4226	0.2464	0.3756	0.024*
C21	0.30950 (5)	0.86157 (7)	0.37333 (4)	0.01587 (11)
H21A	0.3397	0.9115	0.4214	0.019*
H21B	0.2841	0.9303	0.3327	0.019*
C22	0.21975 (5)	0.77395 (9)	0.39250 (4)	0.02000 (13)
H22A	0.1715	0.8334	0.4133	0.030*
H22B	0.2445	0.7044	0.4319	0.030*
H22C	0.1867	0.7290	0.3444	0.030*

	U11	U22	U33	U12	U13	U23
S1	0.01271 (7)	0.00984 (6)	0.01338 (7)	−0.00042 (4)	−0.00136 (5)	−0.00091 (4)
O1	0.0160 (2)	0.01258 (19)	0.0272 (3)	−0.00482 (16)	−0.00210 (18)	0.00116 (17)
O2	0.0232 (2)	0.0180 (2)	0.01203 (19)	0.00396 (17)	−0.00003 (17)	−0.00289 (15)
O3	0.01293 (18)	0.01207 (17)	0.01232 (18)	0.00183 (14)	0.00415 (14)	0.00262 (13)
O4	0.0223 (2)	0.01282 (19)	0.0246 (2)	0.00660 (17)	0.00808 (19)	0.00096 (17)
O5	0.0171 (2)	0.01400 (19)	0.0170 (2)	−0.00069 (15)	0.00842 (16)	0.00159 (15)
N1	0.0117 (2)	0.01097 (18)	0.01199 (19)	−0.00025 (15)	0.00035 (15)	0.00063 (15)
N2	0.0119 (2)	0.01108 (19)	0.0130 (2)	0.00168 (15)	0.00410 (15)	0.00013 (15)
N3	0.0144 (2)	0.00921 (18)	0.0128 (2)	0.00074 (15)	0.00319 (16)	0.00089 (14)
C1	0.0135 (2)	0.0111 (2)	0.0128 (2)	−0.00121 (17)	0.00190 (18)	0.00083 (17)
C2	0.0116 (2)	0.0103 (2)	0.0113 (2)	0.00114 (16)	0.00109 (17)	0.00142 (16)
C3	0.0096 (2)	0.0106 (2)	0.0106 (2)	0.00110 (16)	0.00170 (16)	0.00018 (16)
C4	0.0104 (2)	0.0110 (2)	0.0113 (2)	0.00091 (16)	0.00145 (16)	−0.00006 (16)
C5	0.0126 (2)	0.0122 (2)	0.0115 (2)	0.00189 (17)	0.00177 (17)	0.00231 (17)
C6	0.0096 (2)	0.00993 (19)	0.0111 (2)	0.00013 (16)	0.00149 (16)	0.00011 (16)
C7	0.0100 (2)	0.00933 (19)	0.0112 (2)	0.00002 (16)	0.00243 (16)	0.00026 (16)
C8	0.0106 (2)	0.0112 (2)	0.0131 (2)	0.00007 (16)	0.00020 (17)	0.00090 (17)
C9	0.0124 (2)	0.0130 (2)	0.0139 (2)	0.00026 (17)	0.00232 (18)	0.00160 (17)
C10	0.0134 (2)	0.0122 (2)	0.0162 (2)	0.00041 (18)	0.00204 (18)	0.00224 (18)
C11	0.0130 (2)	0.0128 (2)	0.0168 (2)	0.00140 (18)	0.00108 (19)	0.00025 (19)
C12	0.0151 (3)	0.0158 (2)	0.0196 (3)	0.0021 (2)	0.0060 (2)	0.0020 (2)
C13	0.0136 (2)	0.0139 (2)	0.0176 (3)	0.00009 (18)	0.0042 (2)	0.00289 (19)
C14	0.0212 (3)	0.0142 (2)	0.0264 (3)	0.0046 (2)	0.0058 (2)	0.0002 (2)
C15	0.0218 (3)	0.0159 (3)	0.0160 (2)	0.0006 (2)	0.0054 (2)	0.0053 (2)
C16	0.0140 (2)	0.0202 (3)	0.0120 (2)	0.0018 (2)	−0.00014 (18)	−0.00042 (19)
C17	0.0128 (2)	0.0109 (2)	0.0148 (2)	0.00118 (17)	0.00253 (18)	−0.00002 (17)
C18	0.0108 (2)	0.0098 (2)	0.0122 (2)	−0.00062 (16)	0.00179 (16)	−0.00023 (16)
C19	0.0202 (3)	0.0163 (3)	0.0197 (3)	0.0048 (2)	0.0108 (2)	0.0017 (2)
C20	0.0205 (3)	0.0109 (2)	0.0177 (3)	0.00067 (19)	0.0043 (2)	0.00368 (19)
C21	0.0147 (2)	0.0179 (3)	0.0153 (2)	0.0050 (2)	0.00301 (19)	−0.0024 (2)
C22	0.0132 (3)	0.0310 (4)	0.0163 (3)	0.0044 (2)	0.0041 (2)	0.0025 (2)

S1—O2	1.4348 (6)	C8—C13	1.3954 (9)
S1—O1	1.4376 (6)	C9—C10	1.3914 (9)
S1—N1	1.6271 (6)	C9—H9	0.93
S1—C8	1.7665 (6)	C10—C11	1.3992 (9)
O3—C6	1.3391 (7)	C10—H10	0.93
O3—C5	1.4811 (8)	C11—C12	1.4003 (10)
O4—C17	1.2262 (8)	C11—C14	1.5068 (9)
O5—C18	1.2326 (7)	C12—C13	1.3912 (9)
N1—C1	1.4783 (8)	C12—H12	0.93
N1—C4	1.4917 (8)	C13—H13	0.93
N2—C6	1.3790 (8)	C14—H14A	0.96
N2—C17	1.3867 (8)	C14—H14B	0.96
N2—C19	1.4666 (8)	C14—H14C	0.96
N3—C17	1.3787 (8)	C15—H15A	0.96
N3—C18	1.4026 (8)	C15—H15B	0.96
N3—C20	1.4669 (8)	C15—H15C	0.96
C1—C2	1.5357 (9)	C16—H16A	0.96
C1—H1A	0.97	C16—H16B	0.96
C1—H1B	0.97	C16—H16C	0.96
C2—C5	1.5277 (9)	C19—H19A	0.96
C2—C3	1.5377 (8)	C19—H19B	0.96
C2—H2	0.98	C19—H19C	0.96
C3—C7	1.5091 (8)	C20—H20A	0.96
C3—C4	1.5455 (8)	C20—H20B	0.96
C3—H3	0.98	C20—H20C	0.96
C4—C21	1.5285 (9)	C21—C22	1.5273 (11)
C4—H4	0.98	C21—H21A	0.97
C5—C15	1.5185 (9)	C21—H21B	0.97
C5—C16	1.5236 (9)	C22—H22A	0.96
C6—C7	1.3627 (8)	C22—H22B	0.96
C7—C18	1.4405 (8)	C22—H22C	0.96
C8—C9	1.3940 (9)
O2—S1—O1	120.86 (3)	C9—C10—H10	119.5
O2—S1—N1	107.07 (3)	C11—C10—H10	119.5
O1—S1—N1	106.28 (3)	C10—C11—C12	118.52 (6)
O2—S1—C8	107.01 (3)	C10—C11—C14	120.40 (6)
O1—S1—C8	107.69 (3)	C12—C11—C14	121.08 (6)
N1—S1—C8	107.27 (3)	C13—C12—C11	121.05 (6)
C6—O3—C5	116.05 (5)	C13—C12—H12	119.5
C1—N1—C4	112.02 (5)	C11—C12—H12	119.5
C1—N1—S1	118.22 (4)	C12—C13—C8	119.44 (6)
C4—N1—S1	118.29 (4)	C12—C13—H13	120.3
C6—N2—C17	121.36 (5)	C8—C13—H13	120.3
C6—N2—C19	121.55 (5)	C11—C14—H14A	109.5
C17—N2—C19	117.06 (5)	C11—C14—H14B	109.5
C17—N3—C18	124.43 (5)	H14A—C14—H14B	109.5
C17—N3—C20	116.67 (5)	C11—C14—H14C	109.5
C18—N3—C20	118.85 (5)	H14A—C14—H14C	109.5
N1—C1—C2	102.97 (5)	H14B—C14—H14C	109.5
N1—C1—H1A	111.2	C5—C15—H15A	109.5
C2—C1—H1A	111.2	C5—C15—H15B	109.5
N1—C1—H1B	111.2	H15A—C15—H15B	109.5
C2—C1—H1B	111.2	C5—C15—H15C	109.5
H1A—C1—H1B	109.1	H15A—C15—H15C	109.5
C5—C2—C1	113.53 (5)	H15B—C15—H15C	109.5
C5—C2—C3	112.41 (5)	C5—C16—H16A	109.5
C1—C2—C3	103.53 (5)	C5—C16—H16B	109.5
C5—C2—H2	109.1	H16A—C16—H16B	109.5
C1—C2—H2	109.1	C5—C16—H16C	109.5
C3—C2—H2	109.1	H16A—C16—H16C	109.5
C7—C3—C2	109.20 (5)	H16B—C16—H16C	109.5
C7—C3—C4	112.71 (5)	O4—C17—N3	122.21 (6)
C2—C3—C4	103.22 (5)	O4—C17—N2	121.22 (6)
C7—C3—H3	110.5	N3—C17—N2	116.56 (5)
C2—C3—H3	110.5	O5—C18—N3	120.03 (5)
C4—C3—H3	110.5	O5—C18—C7	123.51 (5)
N1—C4—C21	110.21 (5)	N3—C18—C7	116.46 (5)
N1—C4—C3	103.29 (5)	N2—C19—H19A	109.5
C21—C4—C3	113.77 (5)	N2—C19—H19B	109.5
N1—C4—H4	109.8	H19A—C19—H19B	109.5
C21—C4—H4	109.8	N2—C19—H19C	109.5
C3—C4—H4	109.8	H19A—C19—H19C	109.5
O3—C5—C15	104.54 (5)	H19B—C19—H19C	109.5
O3—C5—C16	107.92 (5)	N3—C20—H20A	109.5
C15—C5—C16	111.16 (5)	N3—C20—H20B	109.5
O3—C5—C2	108.51 (5)	H20A—C20—H20B	109.5
C15—C5—C2	112.29 (5)	N3—C20—H20C	109.5
C16—C5—C2	112.02 (5)	H20A—C20—H20C	109.5
O3—C6—C7	125.30 (5)	H20B—C20—H20C	109.5
O3—C6—N2	112.40 (5)	C22—C21—C4	112.69 (6)
C7—C6—N2	122.30 (5)	C22—C21—H21A	109.1
C6—C7—C18	118.58 (5)	C4—C21—H21A	109.1
C6—C7—C3	121.95 (5)	C22—C21—H21B	109.1
C18—C7—C3	119.43 (5)	C4—C21—H21B	109.1
C9—C8—C13	120.45 (6)	H21A—C21—H21B	107.8
C9—C8—S1	118.99 (5)	C21—C22—H22A	109.5
C13—C8—S1	120.56 (5)	C21—C22—H22B	109.5
C10—C9—C8	119.49 (6)	H22A—C22—H22B	109.5
C10—C9—H9	120.3	C21—C22—H22C	109.5
C8—C9—H9	120.3	H22A—C22—H22C	109.5
C9—C10—C11	121.05 (6)	H22B—C22—H22C	109.5
O2—S1—N1—C1	172.18 (4)	N2—C6—C7—C3	176.56 (5)
O1—S1—N1—C1	41.74 (5)	C2—C3—C7—C6	−10.74 (8)
C8—S1—N1—C1	−73.25 (5)	C4—C3—C7—C6	−124.84 (6)
O2—S1—N1—C4	−47.28 (5)	C2—C3—C7—C18	171.67 (5)
O1—S1—N1—C4	−177.72 (5)	C4—C3—C7—C18	57.57 (7)
C8—S1—N1—C4	67.29 (5)	O2—S1—C8—C9	21.57 (6)
C4—N1—C1—C2	15.62 (6)	O1—S1—C8—C9	152.92 (5)
S1—N1—C1—C2	158.49 (4)	N1—S1—C8—C9	−93.05 (5)
N1—C1—C2—C5	−155.54 (5)	O2—S1—C8—C13	−158.55 (5)
N1—C1—C2—C3	−33.37 (6)	O1—S1—C8—C13	−27.20 (6)
C5—C2—C3—C7	41.74 (6)	N1—S1—C8—C13	86.83 (6)
C1—C2—C3—C7	−81.18 (5)	C13—C8—C9—C10	−0.94 (9)
C5—C2—C3—C4	161.86 (5)	S1—C8—C9—C10	178.93 (5)
C1—C2—C3—C4	38.94 (6)	C8—C9—C10—C11	0.98 (10)
C1—N1—C4—C21	−113.51 (6)	C9—C10—C11—C12	−0.55 (10)
S1—N1—C4—C21	103.65 (5)	C9—C10—C11—C14	178.68 (6)
C1—N1—C4—C3	8.38 (6)	C10—C11—C12—C13	0.07 (10)
S1—N1—C4—C3	−134.46 (4)	C14—C11—C12—C13	−179.16 (7)
C7—C3—C4—N1	88.77 (5)	C11—C12—C13—C8	−0.04 (11)
C2—C3—C4—N1	−28.91 (6)	C9—C8—C13—C12	0.48 (10)
C7—C3—C4—C21	−151.76 (5)	S1—C8—C13—C12	−179.40 (5)
C2—C3—C4—C21	90.56 (6)	C18—N3—C17—O4	−177.65 (6)
C6—O3—C5—C15	165.61 (5)	C20—N3—C17—O4	−0.07 (10)
C6—O3—C5—C16	−75.98 (6)	C18—N3—C17—N2	0.78 (9)
C6—O3—C5—C2	45.61 (7)	C20—N3—C17—N2	178.35 (6)
C1—C2—C5—O3	57.44 (6)	C6—N2—C17—O4	178.74 (6)
C3—C2—C5—O3	−59.67 (6)	C19—N2—C17—O4	0.17 (10)
C1—C2—C5—C15	−57.61 (7)	C6—N2—C17—N3	0.30 (9)
C3—C2—C5—C15	−174.72 (5)	C19—N2—C17—N3	−178.27 (6)
C1—C2—C5—C16	176.47 (5)	C17—N3—C18—O5	175.47 (6)
C3—C2—C5—C16	59.37 (7)	C20—N3—C18—O5	−2.06 (9)
C5—O3—C6—C7	−15.49 (8)	C17—N3—C18—C7	−4.13 (9)
C5—O3—C6—N2	164.75 (5)	C20—N3—C18—C7	178.34 (6)
C17—N2—C6—O3	−177.85 (5)	C6—C7—C18—O5	−173.12 (6)
C19—N2—C6—O3	0.65 (8)	C3—C7—C18—O5	4.56 (9)
C17—N2—C6—C7	2.38 (9)	C6—C7—C18—N3	6.47 (8)
C19—N2—C6—C7	−179.12 (6)	C3—C7—C18—N3	−175.86 (5)
O3—C6—C7—C18	174.43 (6)	N1—C4—C21—C22	−171.35 (5)
N2—C6—C7—C18	−5.82 (9)	C3—C4—C21—C22	73.20 (7)
O3—C6—C7—C3	−3.19 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5	0.98	2.43	3.0422 (8)	120
C1—H1B···O4i	0.97	2.54	3.5072 (8)	177
C16—H16B···O5ii	0.96	2.57	3.3914 (8)	144
C19—H19C···O1iii	0.96	2.52	3.4006 (9)	153
C20—H20C···O2iv	0.96	2.51	3.2335 (8)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O5	0.98	2.43	3.0422 (8)	120
C1—H1B⋯O4i	0.97	2.54	3.5072 (8)	177
C16—H16B⋯O5ii	0.96	2.57	3.3914 (8)	144
C19—H19C⋯O1iii	0.96	2.52	3.4006 (9)	153
C20—H20C⋯O2iv	0.96	2.51	3.2335 (8)	132

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