6-(3,5-Dimethyl-benz-yl)-5-ethyl-1-[(2-phen-oxy-eth-oxy)meth-yl]-1,2,3,4-tetra-hydro-pyrimidine-2,4-dione.

The six-membered ring of the uracil part of the title compound, C(24)H(28)N(2)O(4), is nearly planar (r.m.s. deviation = 0.013 Å); the aromatic ring of the 3,5-dimethyl-benzyl substitutent is aligned at 85.4 (1)° with respect to this mean plane. The phenyl ring of the substituent at the 1-position takes up two orientations in a 1:1 ratio. In the crystal, two mol-ecules are liked by a pair of N-H⋯O hydrogen bonds, generating a centrosymmetric hydrogen-bonded dimer.

Related literature

For the background to our studies on anti­viral HIV chemicals, see: El-Brollosy et al. (2007 ▶, 2008 ▶, 2009 ▶).

Experimental

Crystal data

C24H28N2O4

M = 408.48

Monoclinic,

a = 16.1116 (6) Å

b = 4.8211 (2) Å

c = 27.5125 (10) Å

β = 92.574 (3)°

V = 2134.90 (14) Å3

Z = 4

Cu Kα radiation

μ = 0.70 mm−1

T = 100 K

0.20 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.873, T max = 0.966

6587 measured reflections

4115 independent reflections

2940 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.03

4115 reflections

272 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039821/xu5341sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039821/xu5341Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039821/xu5341Isup3.cml

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

C24H28N2O4	F(000) = 872
Mr = 408.48	Dx = 1.271 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 1976 reflections
a = 16.1116 (6) Å	θ = 2.7–74.3°
b = 4.8211 (2) Å	µ = 0.70 mm−1
c = 27.5125 (10) Å	T = 100 K
β = 92.574 (3)°	Prism, colorless
V = 2134.90 (14) Å3	0.20 × 0.10 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	4115 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2940 reflections with I > 2σ(I)
Mirror	Rint = 0.036
Detector resolution: 10.4041 pixels mm-1	θmax = 74.4°, θmin = 3.1°
ω scans	h = −17→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −5→5
Tmin = 0.873, Tmax = 0.966	l = −19→34
6587 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0602P)2] where P = (Fo2 + 2Fc2)/3
4115 reflections	(Δ/σ)max = 0.001
272 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.33 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.41200 (10)	0.7342 (4)	0.49973 (5)	0.0225 (4)
H1	0.4438 (15)	0.827 (5)	0.4779 (8)	0.048 (7)*
N2	0.38205 (9)	0.6427 (3)	0.58001 (5)	0.0188 (3)
O1	0.34103 (8)	0.5312 (3)	0.43648 (4)	0.0288 (3)
O2	0.48232 (8)	0.9577 (3)	0.56125 (4)	0.0268 (3)
O3	0.44380 (7)	0.4797 (3)	0.65593 (4)	0.0248 (3)
O4	0.56832 (8)	0.5868 (3)	0.72760 (5)	0.0324 (4)
C1	0.35269 (11)	0.5509 (4)	0.48060 (6)	0.0207 (4)
C2	0.30735 (11)	0.3942 (4)	0.51623 (6)	0.0200 (4)
C3	0.24618 (11)	0.1866 (5)	0.49479 (7)	0.0265 (5)
H3A	0.2372	0.0400	0.5192	0.032*
H3B	0.2706	0.0976	0.4663	0.032*
C4	0.16242 (13)	0.3118 (6)	0.47889 (8)	0.0397 (6)
H4A	0.1283	0.1710	0.4618	0.060*
H4B	0.1711	0.4688	0.4571	0.060*
H4C	0.1341	0.3762	0.5076	0.060*
C5	0.32268 (11)	0.4450 (4)	0.56414 (6)	0.0187 (4)
C6	0.42908 (11)	0.7878 (4)	0.54791 (6)	0.0204 (4)
C7	0.27874 (11)	0.2963 (4)	0.60376 (6)	0.0208 (4)
H7A	0.3209	0.2359	0.6288	0.025*
H7B	0.2525	0.1271	0.5896	0.025*
C8	0.21249 (11)	0.4626 (4)	0.62863 (6)	0.0201 (4)
C9	0.16152 (11)	0.6537 (4)	0.60390 (6)	0.0210 (4)
H9	0.1699	0.6903	0.5705	0.025*
C10	0.09878 (11)	0.7921 (4)	0.62691 (7)	0.0244 (4)
C11	0.08768 (12)	0.7369 (4)	0.67617 (7)	0.0267 (5)
H11	0.0455	0.8325	0.6925	0.032*
C12	0.13705 (11)	0.5453 (4)	0.70170 (6)	0.0244 (4)
C13	0.19980 (11)	0.4113 (4)	0.67758 (6)	0.0229 (4)
H13	0.2346	0.2825	0.6949	0.028*
C14	0.04326 (12)	0.9954 (5)	0.59964 (8)	0.0326 (5)
H14A	0.0550	0.9909	0.5650	0.049*
H14B	0.0535	1.1826	0.6125	0.049*
H14C	−0.0150	0.9453	0.6037	0.049*
C15	0.12262 (13)	0.4790 (5)	0.75430 (7)	0.0335 (5)
H15A	0.1071	0.6487	0.7713	0.050*
H15B	0.1736	0.4029	0.7698	0.050*
H15C	0.0778	0.3424	0.7560	0.050*
C16	0.39924 (11)	0.6934 (4)	0.63250 (6)	0.0212 (4)
H16A	0.4311	0.8682	0.6365	0.025*
H16B	0.3458	0.7180	0.6484	0.025*
C17	0.53086 (11)	0.4743 (5)	0.64639 (7)	0.0297 (5)
H17A	0.5493	0.6616	0.6368	0.036*
H17B	0.5406	0.3453	0.6192	0.036*
C18	0.57914 (12)	0.3821 (5)	0.69086 (7)	0.0317 (5)
H18A	0.5587	0.1998	0.7018	0.038*
H18B	0.6387	0.3638	0.6840	0.038*
C19	0.6138 (7)	0.580 (2)	0.7701 (2)	0.0314 (7)	0.50
C20	0.6750 (6)	0.3880 (17)	0.7837 (2)	0.0428 (16)	0.50
H20	0.6865	0.2373	0.7628	0.051*	0.50
C21	0.7193 (4)	0.4169 (15)	0.8279 (2)	0.0473 (14)	0.50
H21	0.7611	0.2860	0.8373	0.057*	0.50
C22	0.7025 (4)	0.6374 (15)	0.85853 (18)	0.0386 (18)	0.50
H22	0.7328	0.6572	0.8888	0.046*	0.50
C23	0.6413 (6)	0.8290 (14)	0.8449 (2)	0.0400 (17)	0.50
H23	0.6298	0.9797	0.8658	0.048*	0.50
C24	0.5969 (7)	0.800 (2)	0.8007 (2)	0.0365 (14)	0.50
H24	0.5551	0.9309	0.7914	0.044*	0.50
C19'	0.6218 (7)	0.570 (2)	0.7688 (2)	0.0314 (7)	0.50
C20'	0.6910 (6)	0.3974 (18)	0.7719 (2)	0.0428 (16)	0.50
H20'	0.7033	0.2811	0.7453	0.051*	0.50
C21'	0.7423 (4)	0.3952 (17)	0.8139 (2)	0.0473 (14)	0.50
H21'	0.7896	0.2774	0.8160	0.057*	0.50
C22'	0.7244 (4)	0.5654 (18)	0.85281 (19)	0.0386 (18)	0.50
H22'	0.7594	0.5639	0.8815	0.046*	0.50
C23'	0.6552 (5)	0.7379 (15)	0.84974 (19)	0.0400 (17)	0.50
H23'	0.6429	0.8542	0.8764	0.048*	0.50
C24'	0.6039 (6)	0.740 (2)	0.8077 (2)	0.0365 (14)	0.50
H24'	0.5566	0.8579	0.8056	0.044*	0.50

	U11	U22	U33	U12	U13	U23
N1	0.0214 (8)	0.0306 (10)	0.0160 (7)	−0.0053 (7)	0.0047 (6)	0.0009 (7)
N2	0.0188 (7)	0.0235 (9)	0.0142 (7)	−0.0030 (7)	0.0028 (6)	−0.0016 (7)
O1	0.0305 (7)	0.0412 (9)	0.0151 (6)	−0.0050 (7)	0.0035 (5)	−0.0015 (6)
O2	0.0257 (7)	0.0348 (8)	0.0202 (6)	−0.0111 (6)	0.0040 (5)	0.0003 (6)
O3	0.0187 (6)	0.0374 (8)	0.0182 (6)	0.0007 (6)	0.0013 (5)	0.0028 (6)
O4	0.0285 (7)	0.0444 (9)	0.0235 (7)	0.0064 (7)	−0.0068 (6)	−0.0081 (7)
C1	0.0197 (9)	0.0259 (11)	0.0166 (9)	0.0023 (8)	0.0032 (7)	0.0006 (8)
C2	0.0184 (9)	0.0216 (10)	0.0200 (9)	−0.0009 (7)	0.0019 (7)	−0.0011 (8)
C3	0.0287 (11)	0.0323 (12)	0.0186 (9)	−0.0090 (9)	0.0009 (8)	−0.0010 (9)
C4	0.0278 (11)	0.0587 (17)	0.0320 (11)	−0.0065 (11)	−0.0045 (9)	−0.0122 (12)
C5	0.0167 (8)	0.0205 (10)	0.0191 (8)	0.0016 (7)	0.0028 (7)	0.0000 (8)
C6	0.0178 (9)	0.0252 (10)	0.0183 (9)	0.0000 (8)	0.0035 (7)	0.0013 (8)
C7	0.0201 (9)	0.0234 (10)	0.0191 (9)	−0.0024 (8)	0.0031 (7)	−0.0005 (8)
C8	0.0176 (8)	0.0233 (10)	0.0196 (9)	−0.0055 (7)	0.0038 (7)	−0.0007 (8)
C9	0.0194 (9)	0.0253 (10)	0.0185 (9)	−0.0047 (8)	0.0021 (7)	0.0011 (8)
C10	0.0206 (9)	0.0243 (11)	0.0281 (10)	−0.0030 (8)	−0.0001 (8)	−0.0005 (9)
C11	0.0211 (9)	0.0309 (12)	0.0286 (10)	−0.0014 (8)	0.0069 (8)	−0.0041 (9)
C12	0.0213 (9)	0.0336 (12)	0.0186 (9)	−0.0064 (9)	0.0038 (7)	−0.0019 (9)
C13	0.0211 (9)	0.0286 (11)	0.0191 (9)	−0.0024 (8)	0.0010 (7)	0.0042 (8)
C14	0.0253 (10)	0.0321 (12)	0.0405 (12)	0.0011 (9)	0.0010 (9)	0.0029 (11)
C15	0.0292 (10)	0.0508 (15)	0.0210 (10)	−0.0065 (10)	0.0078 (8)	−0.0011 (10)
C16	0.0200 (9)	0.0281 (11)	0.0156 (8)	−0.0024 (8)	0.0022 (7)	−0.0029 (8)
C17	0.0177 (9)	0.0481 (14)	0.0235 (10)	−0.0014 (9)	0.0032 (7)	−0.0040 (10)
C18	0.0258 (10)	0.0389 (13)	0.0301 (11)	0.0067 (9)	−0.0033 (8)	−0.0086 (10)
C19	0.0248 (19)	0.0451 (15)	0.0237 (10)	−0.0112 (13)	−0.0055 (10)	0.0059 (10)
C20	0.040 (4)	0.0552 (19)	0.032 (3)	−0.001 (2)	−0.012 (3)	0.009 (2)
C21	0.039 (4)	0.063 (2)	0.038 (4)	0.002 (3)	−0.013 (2)	0.009 (3)
C22	0.030 (3)	0.058 (4)	0.0265 (18)	−0.013 (3)	−0.008 (2)	0.012 (2)
C23	0.042 (3)	0.059 (5)	0.0179 (14)	−0.010 (3)	−0.0079 (14)	0.011 (2)
C24	0.0328 (18)	0.062 (4)	0.0146 (19)	−0.0076 (19)	−0.0034 (13)	0.006 (2)
C19'	0.0248 (19)	0.0451 (15)	0.0237 (10)	−0.0112 (13)	−0.0055 (10)	0.0059 (10)
C20'	0.040 (4)	0.0552 (19)	0.032 (3)	−0.001 (2)	−0.012 (3)	0.009 (2)
C21'	0.039 (4)	0.063 (2)	0.038 (4)	0.002 (3)	−0.013 (2)	0.009 (3)
C22'	0.030 (3)	0.058 (4)	0.0265 (18)	−0.013 (3)	−0.008 (2)	0.012 (2)
C23'	0.042 (3)	0.059 (5)	0.0179 (14)	−0.010 (3)	−0.0079 (14)	0.011 (2)
C24'	0.0328 (18)	0.062 (4)	0.0146 (19)	−0.0076 (19)	−0.0034 (13)	0.006 (2)

N1—C6	1.366 (2)	C13—H13	0.9500
N1—C1	1.388 (2)	C14—H14A	0.9800
N1—H1	0.92 (3)	C14—H14B	0.9800
N2—C6	1.380 (2)	C14—H14C	0.9800
N2—C5	1.406 (2)	C15—H15A	0.9800
N2—C16	1.479 (2)	C15—H15B	0.9800
O1—C1	1.224 (2)	C15—H15C	0.9800
O2—C6	1.230 (2)	C16—H16A	0.9900
O3—C16	1.396 (2)	C16—H16B	0.9900
O3—C17	1.439 (2)	C17—C18	1.488 (3)
O4—C19	1.352 (6)	C17—H17A	0.9900
O4—C19'	1.395 (6)	C17—H17B	0.9900
O4—C18	1.429 (2)	C18—H18A	0.9900
C1—C2	1.459 (2)	C18—H18B	0.9900
C2—C5	1.352 (2)	C19—C20	1.3900
C2—C3	1.506 (3)	C19—C24	1.3900
C3—C4	1.525 (3)	C20—C21	1.3900
C3—H3A	0.9900	C20—H20	0.9500
C3—H3B	0.9900	C21—C22	1.3900
C4—H4A	0.9800	C21—H21	0.9500
C4—H4B	0.9800	C22—C23	1.3900
C4—H4C	0.9800	C22—H22	0.9500
C5—C7	1.508 (2)	C23—C24	1.3900
C7—C8	1.522 (2)	C23—H23	0.9500
C7—H7A	0.9900	C24—H24	0.9500
C7—H7B	0.9900	C19'—C20'	1.3900
C8—C9	1.392 (3)	C19'—C24'	1.3900
C8—C13	1.393 (2)	C20'—C21'	1.3900
C9—C10	1.388 (3)	C20'—H20'	0.9500
C9—H9	0.9500	C21'—C22'	1.3900
C10—C11	1.401 (3)	C21'—H21'	0.9500
C10—C14	1.504 (3)	C22'—C23'	1.3900
C11—C12	1.389 (3)	C22'—H22'	0.9500
C11—H11	0.9500	C23'—C24'	1.3900
C12—C13	1.393 (3)	C23'—H23'	0.9500
C12—C15	1.510 (2)	C24'—H24'	0.9500
C6—N1—C1	126.42 (16)	H14B—C14—H14C	109.5
C6—N1—H1	116.5 (15)	C12—C15—H15A	109.5
C1—N1—H1	117.1 (15)	C12—C15—H15B	109.5
C6—N2—C5	122.04 (15)	H15A—C15—H15B	109.5
C6—N2—C16	117.20 (15)	C12—C15—H15C	109.5
C5—N2—C16	120.70 (15)	H15A—C15—H15C	109.5
C16—O3—C17	114.49 (15)	H15B—C15—H15C	109.5
C19—O4—C18	121.0 (4)	O3—C16—N2	113.50 (15)
C19'—O4—C18	116.3 (4)	O3—C16—H16A	108.9
O1—C1—N1	119.88 (17)	N2—C16—H16A	108.9
O1—C1—C2	124.54 (18)	O3—C16—H16B	108.9
N1—C1—C2	115.58 (15)	N2—C16—H16B	108.9
C5—C2—C1	119.08 (17)	H16A—C16—H16B	107.7
C5—C2—C3	126.12 (17)	O3—C17—C18	109.48 (15)
C1—C2—C3	114.80 (16)	O3—C17—H17A	109.8
C2—C3—C4	113.85 (18)	C18—C17—H17A	109.8
C2—C3—H3A	108.8	O3—C17—H17B	109.8
C4—C3—H3A	108.8	C18—C17—H17B	109.8
C2—C3—H3B	108.8	H17A—C17—H17B	108.2
C4—C3—H3B	108.8	O4—C18—C17	107.43 (17)
H3A—C3—H3B	107.7	O4—C18—H18A	110.2
C3—C4—H4A	109.5	C17—C18—H18A	110.2
C3—C4—H4B	109.5	O4—C18—H18B	110.2
H4A—C4—H4B	109.5	C17—C18—H18B	110.2
C3—C4—H4C	109.5	H18A—C18—H18B	108.5
H4A—C4—H4C	109.5	O4—C19—C20	126.9 (6)
H4B—C4—H4C	109.5	O4—C19—C24	113.0 (6)
C2—C5—N2	121.15 (16)	C20—C19—C24	120.0
C2—C5—C7	123.20 (17)	C19—C20—C21	120.0
N2—C5—C7	115.65 (15)	C19—C20—H20	120.0
O2—C6—N1	121.52 (16)	C21—C20—H20	120.0
O2—C6—N2	122.85 (16)	C22—C21—C20	120.0
N1—C6—N2	115.63 (16)	C22—C21—H21	120.0
C5—C7—C8	115.86 (16)	C20—C21—H21	120.0
C5—C7—H7A	108.3	C23—C22—C21	120.0
C8—C7—H7A	108.3	C23—C22—H22	120.0
C5—C7—H7B	108.3	C21—C22—H22	120.0
C8—C7—H7B	108.3	C24—C23—C22	120.0
H7A—C7—H7B	107.4	C24—C23—H23	120.0
C9—C8—C13	118.74 (17)	C22—C23—H23	120.0
C9—C8—C7	122.65 (16)	C23—C24—C19	120.0
C13—C8—C7	118.53 (17)	C23—C24—H24	120.0
C10—C9—C8	121.43 (17)	C19—C24—H24	120.0
C10—C9—H9	119.3	C20'—C19'—C24'	120.0
C8—C9—H9	119.3	C20'—C19'—O4	123.3 (6)
C9—C10—C11	118.53 (18)	C24'—C19'—O4	116.7 (6)
C9—C10—C14	120.98 (17)	C19'—C20'—C21'	120.0
C11—C10—C14	120.49 (18)	C19'—C20'—H20'	120.0
C12—C11—C10	121.36 (18)	C21'—C20'—H20'	120.0
C12—C11—H11	119.3	C20'—C21'—C22'	120.0
C10—C11—H11	119.3	C20'—C21'—H21'	120.0
C11—C12—C13	118.63 (17)	C22'—C21'—H21'	120.0
C11—C12—C15	121.06 (18)	C23'—C22'—C21'	120.0
C13—C12—C15	120.30 (18)	C23'—C22'—H22'	120.0
C12—C13—C8	121.29 (18)	C21'—C22'—H22'	120.0
C12—C13—H13	119.4	C22'—C23'—C24'	120.0
C8—C13—H13	119.4	C22'—C23'—H23'	120.0
C10—C14—H14A	109.5	C24'—C23'—H23'	120.0
C10—C14—H14B	109.5	C23'—C24'—C19'	120.0
H14A—C14—H14B	109.5	C23'—C24'—H24'	120.0
C10—C14—H14C	109.5	C19'—C24'—H24'	120.0
H14A—C14—H14C	109.5
C6—N1—C1—O1	176.73 (18)	C15—C12—C13—C8	177.89 (18)
C6—N1—C1—C2	−2.7 (3)	C9—C8—C13—C12	0.6 (3)
O1—C1—C2—C5	−176.43 (18)	C7—C8—C13—C12	−176.36 (17)
N1—C1—C2—C5	3.0 (3)	C17—O3—C16—N2	75.77 (19)
O1—C1—C2—C3	3.4 (3)	C6—N2—C16—O3	−104.31 (19)
N1—C1—C2—C3	−177.20 (16)	C5—N2—C16—O3	72.9 (2)
C5—C2—C3—C4	97.0 (2)	C16—O3—C17—C18	144.73 (17)
C1—C2—C3—C4	−82.8 (2)	C19—O4—C18—C17	−170.9 (7)
C1—C2—C5—N2	−0.8 (3)	C19'—O4—C18—C17	−167.2 (6)
C3—C2—C5—N2	179.36 (17)	O3—C17—C18—O4	−64.1 (2)
C1—C2—C5—C7	179.49 (17)	C19'—O4—C19—C20	−35 (10)
C3—C2—C5—C7	−0.3 (3)	C18—O4—C19—C20	1.0 (12)
C6—N2—C5—C2	−2.0 (3)	C19'—O4—C19—C24	142 (11)
C16—N2—C5—C2	−179.04 (17)	C18—O4—C19—C24	177.9 (3)
C6—N2—C5—C7	177.74 (16)	O4—C19—C20—C21	176.7 (12)
C16—N2—C5—C7	0.7 (2)	C24—C19—C20—C21	0.0
C1—N1—C6—O2	−178.95 (17)	C19—C20—C21—C22	0.0
C1—N1—C6—N2	0.1 (3)	C20—C21—C22—C23	0.0
C5—N2—C6—O2	−178.63 (17)	C21—C22—C23—C24	0.0
C16—N2—C6—O2	−1.5 (3)	C22—C23—C24—C19	0.0
C5—N2—C6—N1	2.3 (3)	O4—C19—C24—C23	−177.1 (10)
C16—N2—C6—N1	179.49 (16)	C20—C19—C24—C23	0.0
C2—C5—C7—C8	−104.9 (2)	C19—O4—C19'—C20'	156 (11)
N2—C5—C7—C8	75.4 (2)	C18—O4—C19'—C20'	10.5 (10)
C5—C7—C8—C9	35.4 (2)	C19—O4—C19'—C24'	−25 (10)
C5—C7—C8—C13	−147.79 (18)	C18—O4—C19'—C24'	−170.5 (4)
C13—C8—C9—C10	−0.2 (3)	C24'—C19'—C20'—C21'	0.0
C7—C8—C9—C10	176.65 (18)	O4—C19'—C20'—C21'	178.9 (11)
C8—C9—C10—C11	0.4 (3)	C19'—C20'—C21'—C22'	0.0
C8—C9—C10—C14	−179.14 (17)	C20'—C21'—C22'—C23'	0.0
C9—C10—C11—C12	−1.0 (3)	C21'—C22'—C23'—C24'	0.0
C14—C10—C11—C12	178.52 (18)	C22'—C23'—C24'—C19'	0.0
C10—C11—C12—C13	1.4 (3)	C20'—C19'—C24'—C23'	0.0
C10—C11—C12—C15	−177.69 (19)	O4—C19'—C24'—C23'	−179.0 (10)
C11—C12—C13—C8	−1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.92 (3)	1.94 (3)	2.859 (2)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.92 (3)	1.94 (3)	2.859 (2)	173 (2)

Symmetry code: (i) .