1-tert-Butyl 2-ethyl 5-chloro-3-(2-furo-yl)-1H-indole-1,2-dicarboxyl-ate.

In the title compound, C21H20ClNO6, the furan moiety is located above the mean plane of the indole ring and displays rotational disorder (i.e. rotation through 180°); the site occupancy of the major component is 0.809 (6). In the crystal, C-H⋯O inter-actions link the mol-ecules into chains which run parallel to the b axis.

Related literature

For background to the use of indoles as scaffolds in the synthesis of HIV-agents, see: Hassam et al. (2012 ▶) and for a recent review on stages of non-nucleoside reverse transcriptase inhibitors, see: Reynolds et al. (2012 ▶). For the crystal structures of closely related compounds, see: Beddoes et al. (1986 ▶), Hassam & Smith (2012 ▶, 2013 ▶).

Experimental

Crystal data

C21H20ClNO6

M = 417.83

Monoclinic,

a = 9.8354 (8) Å

b = 8.0938 (7) Å

c = 25.435 (2) Å

β = 99.344 (1)°

V = 1997.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.32 × 0.32 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.930, T max = 0.947

11690 measured reflections

4483 independent reflections

3877 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.084

S = 1.05

4483 reflections

279 parameters

8 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶; Atwood & Barbour, 2003 ▶); software used to prepare material for publication: X-SEED.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005059/zl2535sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005059/zl2535Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005059/zl2535Isup3.cml

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

C21H20ClNO6	F(000) = 872
Mr = 417.83	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Melting point: 378(2) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.8354 (8) Å	Cell parameters from 5304 reflections
b = 8.0938 (7) Å	θ = 2.4–27.9°
c = 25.435 (2) Å	µ = 0.23 mm−1
β = 99.344 (1)°	T = 100 K
V = 1997.9 (3) Å3	Square block, colourless
Z = 4	0.32 × 0.32 × 0.24 mm

Bruker APEXII CCD diffractometer	4483 independent reflections
Radiation source: fine-focus sealed tube, Bruker SMART Apex	3877 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 28.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→13
Tmin = 0.930, Tmax = 0.947	k = −10→4
11690 measured reflections	l = −31→33

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0359P)2 + 0.8831P] where P = (Fo2 + 2Fc2)/3
4483 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.29 e Å−3
8 restraints	Δρmin = −0.38 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	Occ. (<1)
Cl1	0.77842 (4)	0.54454 (4)	−0.051345 (13)	0.02592 (10)
O1	0.25661 (9)	0.04213 (12)	0.01491 (4)	0.0207 (2)
N1	0.45710 (11)	0.11938 (13)	0.06875 (4)	0.0152 (2)
C1	0.53993 (13)	0.12814 (16)	0.11858 (5)	0.0157 (3)
O2	0.27094 (9)	0.06519 (12)	0.10504 (3)	0.0189 (2)
C2	0.51962 (13)	0.21382 (16)	0.03288 (5)	0.0157 (2)
O3	0.50752 (10)	−0.12594 (12)	0.16190 (4)	0.0223 (2)
C3	0.47829 (14)	0.24137 (16)	−0.02143 (5)	0.0190 (3)
H3	0.3964	0.1936	−0.0403	0.023*
O4	0.51187 (10)	0.11461 (12)	0.20738 (3)	0.0206 (2)
C4	0.56192 (13)	0.34160 (16)	−0.04673 (5)	0.0214 (3)
H4	0.5379	0.3624	−0.0838	0.026*
O5	0.81234 (10)	0.13738 (12)	0.18938 (4)	0.0221 (2)
C5	0.68105 (13)	0.41230 (16)	−0.01829 (5)	0.0198 (3)
C6	0.72402 (13)	0.38397 (15)	0.03549 (5)	0.0178 (3)
H6	0.8068	0.4308	0.0540	0.021*
C7	0.64034 (12)	0.28344 (15)	0.06143 (5)	0.0160 (3)
C8	0.65137 (13)	0.22643 (16)	0.11585 (5)	0.0158 (2)
C9	0.76525 (12)	0.25249 (16)	0.16090 (5)	0.0167 (3)
C10	0.81371 (13)	0.42143 (17)	0.17023 (5)	0.0177 (3)
C14	0.51626 (12)	0.02212 (16)	0.16433 (5)	0.0161 (3)
C15	0.50330 (16)	0.02643 (19)	0.25714 (5)	0.0262 (3)
H15A	0.4507	−0.0773	0.2490	0.031*
H15B	0.4537	0.0955	0.2800	0.031*
C16	0.64444 (18)	−0.0127 (2)	0.28626 (6)	0.0386 (4)
H16A	0.6977	0.0897	0.2930	0.058*
H16C	0.6911	−0.0873	0.2646	0.058*
H16B	0.6370	−0.0660	0.3203	0.058*
C17	0.31674 (13)	0.06954 (16)	0.05885 (5)	0.0164 (3)
C18	0.12943 (13)	0.00596 (17)	0.10920 (5)	0.0191 (3)
C19	0.02392 (14)	0.12342 (19)	0.07961 (6)	0.0266 (3)
H19A	0.0349	0.1279	0.0420	0.040*
H19B	0.0376	0.2340	0.0953	0.040*
H19C	−0.0690	0.0843	0.0824	0.040*
C20	0.13131 (15)	0.01449 (19)	0.16902 (6)	0.0255 (3)
H20A	0.1547	0.1270	0.1816	0.038*
H20B	0.2002	−0.0629	0.1870	0.038*
H20C	0.0402	−0.0151	0.1770	0.038*
C21	0.11243 (16)	−0.16979 (18)	0.08904 (6)	0.0272 (3)
H21A	0.1883	−0.2376	0.1072	0.041*
H21C	0.1133	−0.1715	0.0506	0.041*
H21B	0.0246	−0.2142	0.0963	0.041*
O6A	0.9318 (4)	0.4474 (3)	0.20578 (19)	0.0224 (4)	0.809 (6)
C11A	0.7582 (4)	0.5688 (4)	0.1527 (3)	0.0194 (6)	0.809 (6)
H11A	0.6773	0.5851	0.1273	0.023*	0.809 (6)
C12A	0.8436 (3)	0.6940 (4)	0.17952 (12)	0.0211 (6)	0.809 (6)
H12A	0.8306	0.8101	0.1763	0.025*	0.809 (6)
C13A	0.9470 (3)	0.6138 (4)	0.21058 (12)	0.0242 (6)	0.809 (6)
H13A	1.0210	0.6668	0.2329	0.029*	0.809 (6)
O6B	0.7353 (13)	0.5546 (12)	0.1514 (8)	0.0194 (6)	0.191 (6)
C11B	0.929 (2)	0.4726 (19)	0.2027 (13)	0.0224 (4)	0.191 (6)
H11B	0.9978	0.4049	0.2228	0.027*	0.191 (6)
C12B	0.9271 (18)	0.6477 (18)	0.2006 (6)	0.0242 (6)	0.191 (6)
H12B	0.9966	0.7204	0.2175	0.029*	0.191 (6)
C13B	0.8072 (14)	0.691 (2)	0.1701 (6)	0.0211 (6)	0.191 (6)
H13B	0.7774	0.8017	0.1628	0.025*	0.191 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0375 (2)	0.01775 (17)	0.02629 (18)	0.00140 (14)	0.01670 (14)	0.00393 (13)
O1	0.0191 (5)	0.0232 (5)	0.0189 (5)	−0.0008 (4)	0.0000 (4)	−0.0042 (4)
N1	0.0155 (5)	0.0154 (5)	0.0146 (5)	0.0006 (4)	0.0022 (4)	−0.0001 (4)
C1	0.0157 (6)	0.0156 (6)	0.0155 (6)	0.0022 (5)	0.0014 (4)	−0.0012 (5)
O2	0.0148 (4)	0.0237 (5)	0.0185 (4)	−0.0018 (4)	0.0034 (3)	−0.0016 (4)
C2	0.0172 (6)	0.0141 (6)	0.0168 (6)	0.0033 (5)	0.0054 (5)	−0.0010 (5)
O3	0.0293 (5)	0.0167 (5)	0.0204 (5)	−0.0011 (4)	0.0027 (4)	0.0004 (4)
C3	0.0210 (6)	0.0181 (6)	0.0174 (6)	0.0047 (5)	0.0019 (5)	−0.0017 (5)
O4	0.0288 (5)	0.0186 (5)	0.0156 (4)	−0.0014 (4)	0.0072 (4)	−0.0002 (4)
C4	0.0305 (7)	0.0195 (7)	0.0150 (6)	0.0076 (6)	0.0061 (5)	0.0008 (5)
O5	0.0212 (5)	0.0219 (5)	0.0219 (5)	0.0017 (4)	−0.0003 (4)	0.0036 (4)
C5	0.0266 (7)	0.0141 (6)	0.0214 (6)	0.0045 (5)	0.0122 (5)	0.0022 (5)
C6	0.0186 (6)	0.0150 (6)	0.0207 (6)	0.0029 (5)	0.0061 (5)	0.0005 (5)
C7	0.0173 (6)	0.0145 (6)	0.0165 (6)	0.0041 (5)	0.0038 (5)	−0.0001 (5)
C8	0.0160 (6)	0.0149 (6)	0.0166 (6)	0.0016 (5)	0.0032 (5)	0.0000 (5)
C9	0.0140 (6)	0.0208 (7)	0.0156 (6)	0.0010 (5)	0.0039 (5)	0.0009 (5)
C10	0.0149 (6)	0.0230 (7)	0.0152 (6)	−0.0019 (5)	0.0021 (5)	0.0004 (5)
C14	0.0130 (6)	0.0186 (6)	0.0165 (6)	0.0001 (5)	0.0013 (4)	−0.0002 (5)
C15	0.0401 (8)	0.0247 (7)	0.0161 (6)	−0.0044 (6)	0.0112 (6)	0.0008 (5)
C16	0.0463 (10)	0.0455 (10)	0.0211 (7)	−0.0115 (8)	−0.0030 (7)	0.0079 (7)
C17	0.0149 (6)	0.0137 (6)	0.0203 (6)	0.0021 (5)	0.0025 (5)	−0.0009 (5)
C18	0.0133 (6)	0.0207 (7)	0.0239 (7)	−0.0016 (5)	0.0051 (5)	−0.0025 (5)
C19	0.0182 (7)	0.0284 (8)	0.0327 (8)	0.0033 (6)	0.0033 (6)	−0.0008 (6)
C20	0.0216 (7)	0.0316 (8)	0.0249 (7)	−0.0040 (6)	0.0091 (5)	−0.0031 (6)
C21	0.0283 (7)	0.0214 (7)	0.0340 (8)	−0.0049 (6)	0.0114 (6)	−0.0045 (6)
O6A	0.0205 (5)	0.0241 (9)	0.0202 (8)	−0.0030 (8)	−0.0043 (4)	0.0034 (10)
C11A	0.0118 (14)	0.0253 (9)	0.0207 (7)	−0.0007 (9)	0.0015 (12)	0.0004 (8)
C12A	0.0194 (16)	0.0205 (7)	0.0230 (14)	−0.0035 (13)	0.0019 (11)	0.0011 (9)
C13A	0.0259 (12)	0.0246 (15)	0.0199 (14)	−0.0089 (10)	−0.0031 (8)	0.0012 (9)
O6B	0.0118 (14)	0.0253 (9)	0.0207 (7)	−0.0007 (9)	0.0015 (12)	0.0004 (8)
C11B	0.0205 (5)	0.0241 (9)	0.0202 (8)	−0.0030 (8)	−0.0043 (4)	0.0034 (10)
C12B	0.0259 (12)	0.0246 (15)	0.0199 (14)	−0.0089 (10)	−0.0031 (8)	0.0012 (9)
C13B	0.0194 (16)	0.0205 (7)	0.0230 (14)	−0.0035 (13)	0.0019 (11)	0.0011 (9)

Cl1—C5	1.7411 (13)	C15—H15A	0.9900
O1—C17	1.1973 (15)	C15—H15B	0.9900
N1—C1	1.3929 (15)	C16—H16A	0.9800
N1—C2	1.4059 (16)	C16—H16C	0.9800
N1—C17	1.4209 (16)	C16—H16B	0.9800
C1—C8	1.3651 (18)	C18—C21	1.5121 (19)
C1—C14	1.4943 (17)	C18—C19	1.5145 (19)
O2—C17	1.3253 (15)	C18—C20	1.5203 (19)
O2—C18	1.4919 (15)	C19—H19A	0.9800
C2—C3	1.3933 (17)	C19—H19B	0.9800
C2—C7	1.4053 (17)	C19—H19C	0.9800
O3—C14	1.2023 (16)	C20—H20A	0.9800
C3—C4	1.3859 (19)	C20—H20B	0.9800
C3—H3	0.9500	C20—H20C	0.9800
O4—C14	1.3329 (15)	C21—H21A	0.9800
O4—C15	1.4672 (16)	C21—H21C	0.9800
C4—C5	1.3959 (14)	C21—H21B	0.9800
C4—H4	0.9500	O6A—C13A	1.359 (3)
O5—C9	1.2240 (16)	C11A—C12A	1.418 (3)
C5—C6	1.3836 (13)	C11A—H11A	0.9500
C6—C7	1.3968 (13)	C12A—C13A	1.349 (3)
C6—H6	0.9500	C12A—H12A	0.9500
C7—C8	1.4463 (16)	C13A—H13A	0.9500
C8—C9	1.4816 (17)	O6B—C13B	1.357 (3)
C9—C10	1.4548 (19)	C11B—C12B	1.418 (4)
C10—C11A	1.357 (3)	C11B—H11B	0.9500
C10—C11B	1.357 (4)	C12B—C13B	1.348 (3)
C10—O6B	1.366 (3)	C12B—H12B	0.9500
C10—O6A	1.367 (2)	C13B—H13B	0.9500
C15—C16	1.497 (2)
C1—N1—C2	108.06 (10)	H16A—C16—H16C	109.5
C1—N1—C17	125.70 (10)	C15—C16—H16B	109.5
C2—N1—C17	123.65 (10)	H16A—C16—H16B	109.5
C8—C1—N1	109.83 (11)	H16C—C16—H16B	109.5
C8—C1—C14	127.02 (11)	O1—C17—O2	129.43 (12)
N1—C1—C14	122.51 (11)	O1—C17—N1	122.44 (12)
C17—O2—C18	121.78 (10)	O2—C17—N1	108.11 (10)
C3—C2—C7	122.29 (12)	O2—C18—C21	109.35 (11)
C3—C2—N1	129.98 (12)	O2—C18—C19	109.57 (11)
C7—C2—N1	107.74 (10)	C21—C18—C19	113.13 (12)
C4—C3—C2	117.04 (12)	O2—C18—C20	101.33 (10)
C4—C3—H3	121.5	C21—C18—C20	111.39 (12)
C2—C3—H3	121.5	C19—C18—C20	111.40 (12)
C14—O4—C15	116.71 (10)	C18—C19—H19A	109.5
C3—C4—C5	120.71 (12)	C18—C19—H19B	109.5
C3—C4—H4	119.6	H19A—C19—H19B	109.5
C5—C4—H4	119.6	C18—C19—H19C	109.5
C6—C5—C4	122.72 (12)	H19A—C19—H19C	109.5
C6—C5—Cl1	118.40 (9)	H19B—C19—H19C	109.5
C4—C5—Cl1	118.87 (9)	C18—C20—H20A	109.5
C5—C6—C7	117.05 (11)	C18—C20—H20B	109.5
C5—C6—H6	121.5	H20A—C20—H20B	109.5
C7—C6—H6	121.5	C18—C20—H20C	109.5
C6—C7—C2	120.18 (11)	H20A—C20—H20C	109.5
C6—C7—C8	132.81 (11)	H20B—C20—H20C	109.5
C2—C7—C8	107.00 (10)	C18—C21—H21A	109.5
C1—C8—C7	107.37 (11)	C18—C21—H21C	109.5
C1—C8—C9	123.78 (11)	H21A—C21—H21C	109.5
C7—C8—C9	128.65 (11)	C18—C21—H21B	109.5
O5—C9—C10	122.45 (11)	H21A—C21—H21B	109.5
O5—C9—C8	121.01 (12)	H21C—C21—H21B	109.5
C10—C9—C8	116.51 (11)	C13A—O6A—C10	106.33 (19)
C11A—C10—C11B	100.6 (7)	C10—C11A—C12A	107.2 (3)
C11B—C10—O6B	110.0 (9)	C10—C11A—H11A	126.4
C11A—C10—O6A	109.6 (2)	C12A—C11A—H11A	126.4
O6B—C10—O6A	118.8 (7)	C13A—C12A—C11A	105.6 (3)
C11A—C10—C9	132.0 (2)	C13A—C12A—H12A	127.2
C11B—C10—C9	127.3 (7)	C11A—C12A—H12A	127.2
O6B—C10—C9	122.2 (6)	C12A—C13A—O6A	111.3 (3)
O6A—C10—C9	118.21 (14)	C12A—C13A—H13A	124.4
O3—C14—O4	126.20 (12)	O6A—C13A—H13A	124.4
O3—C14—C1	123.44 (12)	C13B—O6B—C10	106.7 (13)
O4—C14—C1	110.32 (11)	C10—C11B—C12B	106.0 (11)
O4—C15—C16	110.56 (12)	C10—C11B—H11B	127.0
O4—C15—H15A	109.5	C12B—C11B—H11B	127.0
C16—C15—H15A	109.5	C13B—C12B—C11B	106.8 (15)
O4—C15—H15B	109.5	C13B—C12B—H12B	126.6
C16—C15—H15B	109.5	C11B—C12B—H12B	126.6
H15A—C15—H15B	108.1	C12B—C13B—O6B	110.3 (17)
C15—C16—H16A	109.5	C12B—C13B—H13B	124.9
C15—C16—H16C	109.5	O6B—C13B—H13B	124.9
C2—N1—C1—C8	0.90 (14)	C8—C9—C10—O6A	−170.0 (3)
C17—N1—C1—C8	−161.26 (11)	C15—O4—C14—O3	3.66 (19)
C2—N1—C1—C14	−170.51 (11)	C15—O4—C14—C1	−173.96 (11)
C17—N1—C1—C14	27.33 (19)	C8—C1—C14—O3	−116.54 (15)
C1—N1—C2—C3	178.85 (13)	N1—C1—C14—O3	53.33 (18)
C17—N1—C2—C3	−18.5 (2)	C8—C1—C14—O4	61.16 (17)
C1—N1—C2—C7	−1.16 (13)	N1—C1—C14—O4	−128.97 (12)
C17—N1—C2—C7	161.45 (11)	C14—O4—C15—C16	88.55 (15)
C7—C2—C3—C4	0.00 (19)	C18—O2—C17—O1	6.0 (2)
N1—C2—C3—C4	179.99 (12)	C18—O2—C17—N1	−175.66 (10)
C2—C3—C4—C5	−0.72 (19)	C1—N1—C17—O1	−169.19 (12)
C3—C4—C5—C6	1.7 (2)	C2—N1—C17—O1	31.29 (19)
C3—C4—C5—Cl1	−177.20 (10)	C1—N1—C17—O2	12.35 (17)
C4—C5—C6—C7	−1.74 (19)	C2—N1—C17—O2	−147.17 (11)
Cl1—C5—C6—C7	177.11 (9)	C17—O2—C18—C21	58.82 (15)
C5—C6—C7—C2	0.99 (18)	C17—O2—C18—C19	−65.71 (15)
C5—C6—C7—C8	179.53 (13)	C17—O2—C18—C20	176.51 (11)
C3—C2—C7—C6	−0.15 (19)	C11A—C10—O6A—C13A	0.9 (6)
N1—C2—C7—C6	179.86 (11)	C11B—C10—O6A—C13A	14 (13)
C3—C2—C7—C8	−179.03 (12)	O6B—C10—O6A—C13A	−4.8 (11)
N1—C2—C7—C8	0.98 (13)	C9—C10—O6A—C13A	−174.7 (3)
N1—C1—C8—C7	−0.28 (14)	C11B—C10—C11A—C12A	−3.5 (19)
C14—C1—C8—C7	170.64 (12)	O6B—C10—C11A—C12A	150 (7)
N1—C1—C8—C9	−175.47 (11)	O6A—C10—C11A—C12A	−1.5 (6)
C14—C1—C8—C9	−4.5 (2)	C9—C10—C11A—C12A	173.4 (2)
C6—C7—C8—C1	−179.12 (13)	C10—C11A—C12A—C13A	1.4 (5)
C2—C7—C8—C1	−0.44 (14)	C11A—C12A—C13A—O6A	−0.8 (5)
C6—C7—C8—C9	−4.2 (2)	C10—O6A—C13A—C12A	0.0 (5)
C2—C7—C8—C9	174.43 (12)	C11A—C10—O6B—C13B	−24 (5)
C1—C8—C9—O5	41.90 (19)	C11B—C10—O6B—C13B	3 (3)
C7—C8—C9—O5	−132.21 (14)	O6A—C10—O6B—C13B	6.5 (19)
C1—C8—C9—C10	−136.08 (13)	C9—C10—O6B—C13B	176.0 (10)
C7—C8—C9—C10	49.81 (18)	C11A—C10—C11B—C12B	0 (3)
O5—C9—C10—C11A	−162.5 (4)	O6B—C10—C11B—C12B	−5 (3)
C8—C9—C10—C11A	15.5 (4)	O6A—C10—C11B—C12B	−167 (15)
O5—C9—C10—C11B	14 (2)	C9—C10—C11B—C12B	−176.6 (12)
C8—C9—C10—C11B	−168 (2)	C10—C11B—C12B—C13B	4 (3)
O5—C9—C10—O6B	−157.6 (11)	C11B—C12B—C13B—O6B	−2 (3)
C8—C9—C10—O6B	20.4 (11)	C10—O6B—C13B—C12B	−1 (2)
O5—C9—C10—O6A	12.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.95	2.45	2.9774 (16)	115
C13A—H13A···O5i	0.95	2.37	3.187 (3)	144
C19—H19A···O1	0.98	2.49	3.0985 (17)	120
C21—H21C···O1	0.98	2.49	3.0615 (17)	117

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13A—H13A⋯O5i	0.95	2.37	3.187 (3)	144

Symmetry code: (i) .