1-(4-Meth-oxy-phen-yl)-4-(3-nitro-phen-yl)-3-phen-oxy-azetidin-2-one.

In the title compound, C(22)H(18)N(2)O(5), the four-membered β-lactam ring is nearly planar, with a maximum deviation of 0.023 (2) Å for the N atom, and has long C-C distances of 1.525 (5) and 1.571 (5) Å. The mean plane of this group makes dihedral angles of 11.61 (19), 74.5 (2) and 72.3 (2)° with three aromatic rings. An intra-molecular C-H⋯O hydrogen bond occurs. The packing of the mol-ecules in the crystal structure is governed mainly by inter-molecular C-H⋯O hydrogen-bonding and C-H⋯π stacking inter-actions. Furthermore, a π-π inter-action [centroid-centroid distance = 3.6129 (19) Å] helps to stabilize the crystal structure.

Related literature

For general background to β-lactams, see: Jubie et al. (2009 ▶); Mehta et al. (2010 ▶); Vatmurge et al. (2008 ▶); Von Nussbaum et al. (2006 ▶). For related structures, see: Akkurt et al. (2006 ▶); Ercan et al. (1996a ▶,b ▶); Kabak et al. (1999 ▶).

Experimental

Crystal data

C22H18N2O5

M = 390.38

Triclinic,

a = 7.7934 (4) Å

b = 11.2813 (3) Å

c = 11.8818 (2) Å

α = 77.771 (4)°

β = 80.948 (5)°

γ = 71.052 (4)°

V = 961.18 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.981, T max = 0.981

3928 measured reflections

3928 independent reflections

1872 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.155

S = 1.01

3927 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003382/bv2175sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003382/bv2175Isup2.hkl

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

C22H18N2O5	Z = 2
Mr = 390.38	F(000) = 408
Triclinic, P1	Dx = 1.349 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7934 (4) Å	Cell parameters from 2243 reflections
b = 11.2813 (3) Å	θ = 2.4–26.4°
c = 11.8818 (2) Å	µ = 0.10 mm−1
α = 77.771 (4)°	T = 294 K
β = 80.948 (5)°	Block, white
γ = 71.052 (4)°	0.20 × 0.20 × 0.20 mm
V = 961.18 (6) Å3

Rigaku R-AXIS RAPID-S diffractometer	3928 independent reflections
Radiation source: Sealed Tube	1872 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.104
Detector resolution: 10.0000 pixels mm-1	θmax = 26.4°, θmin = 2.4°
dtprofit.ref scans	h = −9→8
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −14→14
Tmin = 0.981, Tmax = 0.981	l = −14→14
3928 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.1692P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3927 reflections	Δρmax = 0.14 e Å−3
265 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.3243 (3)	0.0941 (2)	0.8790 (2)	0.0917 (11)
O2	0.1966 (3)	0.7038 (2)	0.9341 (2)	0.0857 (10)
O3	0.4720 (3)	0.83418 (19)	0.77456 (17)	0.0652 (8)
O4	1.1375 (4)	0.6731 (3)	0.5285 (3)	0.1139 (15)
O5	1.0633 (4)	0.6949 (3)	0.3578 (2)	0.1081 (12)
N1	0.4469 (3)	0.5569 (2)	0.85135 (19)	0.0577 (9)
N2	1.0324 (4)	0.6750 (3)	0.4631 (3)	0.0780 (12)
C1	0.2353 (4)	0.4324 (3)	0.8902 (2)	0.0624 (11)
C2	0.2021 (4)	0.3172 (3)	0.8986 (2)	0.0647 (12)
C3	0.3412 (5)	0.2117 (3)	0.8731 (3)	0.0666 (12)
C4	0.5155 (4)	0.2219 (3)	0.8378 (3)	0.0671 (12)
C5	0.5496 (4)	0.3360 (3)	0.8297 (2)	0.0610 (11)
C6	0.4099 (4)	0.4414 (3)	0.8569 (2)	0.0553 (11)
C7	0.1492 (5)	0.0772 (4)	0.9103 (4)	0.1053 (17)
C8	0.6129 (4)	0.5948 (3)	0.8068 (2)	0.0558 (11)
C9	0.5111 (4)	0.7211 (3)	0.8556 (3)	0.0615 (11)
C10	0.3500 (5)	0.6679 (3)	0.8888 (3)	0.0644 (11)
C11	0.6576 (4)	0.6108 (3)	0.6781 (2)	0.0508 (10)
C12	0.8247 (4)	0.6260 (3)	0.6300 (2)	0.0540 (11)
C13	0.8581 (4)	0.6524 (3)	0.5124 (3)	0.0581 (11)
C14	0.7338 (4)	0.6619 (3)	0.4389 (3)	0.0670 (11)
C15	0.5691 (4)	0.6437 (3)	0.4861 (3)	0.0686 (14)
C16	0.5310 (4)	0.6203 (3)	0.6038 (2)	0.0587 (11)
C17	0.6128 (5)	0.8875 (3)	0.7357 (3)	0.0613 (11)
C18	0.7756 (5)	0.8490 (3)	0.7842 (3)	0.0723 (14)
C19	0.9081 (5)	0.9080 (4)	0.7365 (3)	0.0854 (17)
C20	0.8791 (6)	1.0018 (4)	0.6426 (4)	0.0912 (17)
C21	0.7173 (6)	1.0394 (4)	0.5945 (3)	0.0921 (19)
C22	0.5827 (5)	0.9832 (3)	0.6415 (3)	0.0776 (14)
H1	0.14070	0.50350	0.90690	0.0750*
H2	0.08510	0.31120	0.92160	0.0780*
H4	0.60970	0.15120	0.81950	0.0800*
H5	0.66640	0.34220	0.80600	0.0730*
H7A	0.10340	0.09920	0.98540	0.1580*
H7B	0.15800	−0.01000	0.91200	0.1580*
H7C	0.06770	0.13100	0.85450	0.1580*
H8	0.71820	0.54210	0.84860	0.0670*
H9	0.56390	0.72760	0.92280	0.0740*
H12	0.91340	0.61820	0.67740	0.0650*
H14	0.75970	0.68020	0.35910	0.0800*
H15	0.48370	0.64740	0.43790	0.0820*
H16	0.41810	0.61050	0.63460	0.0700*
H18	0.79670	0.78430	0.84820	0.0870*
H19	1.01790	0.88290	0.76940	0.1020*
H20	0.96880	1.04030	0.61090	0.1100*
H21	0.69770	1.10320	0.52980	0.1110*
H22	0.47220	1.01030	0.60930	0.0930*

	U11	U22	U33	U12	U13	U23
O1	0.0952 (19)	0.0874 (18)	0.110 (2)	−0.0523 (15)	0.0269 (15)	−0.0420 (15)
O2	0.0738 (17)	0.0895 (18)	0.0920 (18)	−0.0269 (13)	0.0240 (14)	−0.0320 (14)
O3	0.0733 (15)	0.0599 (14)	0.0622 (14)	−0.0235 (11)	−0.0041 (11)	−0.0064 (11)
O4	0.0638 (18)	0.150 (3)	0.132 (3)	−0.0557 (18)	−0.0014 (17)	−0.002 (2)
O5	0.100 (2)	0.125 (2)	0.093 (2)	−0.0523 (17)	0.0469 (16)	−0.0176 (17)
N1	0.0566 (16)	0.0636 (17)	0.0527 (15)	−0.0266 (13)	0.0096 (12)	−0.0074 (13)
N2	0.066 (2)	0.073 (2)	0.089 (2)	−0.0289 (16)	0.0230 (18)	−0.0109 (18)
C1	0.061 (2)	0.068 (2)	0.0576 (19)	−0.0229 (17)	0.0046 (15)	−0.0116 (16)
C2	0.060 (2)	0.082 (2)	0.058 (2)	−0.0335 (19)	0.0078 (15)	−0.0154 (18)
C3	0.078 (2)	0.073 (2)	0.058 (2)	−0.040 (2)	0.0147 (17)	−0.0195 (17)
C4	0.071 (2)	0.074 (2)	0.060 (2)	−0.0284 (18)	0.0115 (16)	−0.0220 (17)
C5	0.059 (2)	0.072 (2)	0.0531 (18)	−0.0277 (17)	0.0127 (15)	−0.0139 (16)
C6	0.062 (2)	0.063 (2)	0.0427 (17)	−0.0280 (16)	0.0036 (14)	−0.0046 (14)
C7	0.109 (3)	0.104 (3)	0.129 (3)	−0.072 (3)	0.032 (3)	−0.045 (3)
C8	0.0566 (18)	0.064 (2)	0.0481 (17)	−0.0249 (16)	−0.0026 (14)	−0.0034 (15)
C9	0.073 (2)	0.066 (2)	0.0484 (17)	−0.0280 (17)	−0.0021 (15)	−0.0074 (16)
C10	0.067 (2)	0.071 (2)	0.0538 (19)	−0.0251 (18)	0.0074 (16)	−0.0105 (17)
C11	0.0441 (16)	0.0544 (18)	0.0525 (17)	−0.0175 (14)	0.0017 (13)	−0.0069 (14)
C12	0.0482 (18)	0.0548 (18)	0.0591 (19)	−0.0182 (14)	−0.0016 (14)	−0.0084 (15)
C13	0.0485 (18)	0.0530 (18)	0.068 (2)	−0.0188 (14)	0.0132 (15)	−0.0084 (16)
C14	0.068 (2)	0.075 (2)	0.0521 (19)	−0.0229 (18)	0.0069 (16)	−0.0058 (16)
C15	0.064 (2)	0.090 (3)	0.056 (2)	−0.0313 (19)	−0.0026 (16)	−0.0112 (18)
C16	0.0503 (18)	0.072 (2)	0.0570 (19)	−0.0273 (16)	0.0007 (14)	−0.0085 (16)
C17	0.074 (2)	0.057 (2)	0.0542 (19)	−0.0249 (17)	0.0033 (16)	−0.0115 (16)
C18	0.087 (3)	0.072 (2)	0.065 (2)	−0.036 (2)	−0.0066 (19)	−0.0086 (18)
C19	0.092 (3)	0.086 (3)	0.087 (3)	−0.044 (2)	0.000 (2)	−0.013 (2)
C20	0.109 (3)	0.081 (3)	0.089 (3)	−0.049 (3)	0.020 (3)	−0.016 (2)
C21	0.120 (4)	0.067 (3)	0.075 (3)	−0.030 (3)	0.014 (3)	0.004 (2)
C22	0.093 (3)	0.067 (2)	0.061 (2)	−0.018 (2)	−0.0005 (19)	−0.0004 (18)

O1—C3	1.361 (4)	C15—C16	1.370 (4)
O1—C7	1.420 (5)	C17—C18	1.377 (6)
O2—C10	1.208 (5)	C17—C22	1.371 (5)
O3—C9	1.403 (4)	C18—C19	1.390 (6)
O3—C17	1.390 (5)	C19—C20	1.356 (6)
O4—N2	1.207 (5)	C20—C21	1.369 (7)
O5—N2	1.223 (4)	C21—C22	1.383 (6)
N1—C6	1.410 (4)	C1—H1	0.9300
N1—C8	1.478 (4)	C2—H2	0.9300
N1—C10	1.361 (4)	C4—H4	0.9300
N2—C13	1.471 (5)	C5—H5	0.9300
C1—C2	1.386 (5)	C7—H7A	0.9600
C1—C6	1.386 (5)	C7—H7B	0.9600
C2—C3	1.377 (5)	C7—H7C	0.9600
C3—C4	1.392 (5)	C8—H8	0.9800
C4—C5	1.378 (5)	C9—H9	0.9800
C5—C6	1.384 (5)	C12—H12	0.9300
C8—C9	1.571 (5)	C14—H14	0.9300
C8—C11	1.500 (3)	C15—H15	0.9300
C9—C10	1.525 (5)	C16—H16	0.9300
C11—C12	1.386 (5)	C18—H18	0.9300
C11—C16	1.389 (4)	C19—H19	0.9300
C12—C13	1.367 (4)	C20—H20	0.9300
C13—C14	1.368 (5)	C21—H21	0.9300
C14—C15	1.378 (5)	C22—H22	0.9300
O1···O3i	3.219 (3)	C5···H9vii	2.9400
O1···C17i	3.234 (4)	C5···H8	3.0800
O1···C22i	3.414 (4)	C6···H16	2.9200
O2···O3	3.155 (3)	C6···H9vii	2.8900
O2···C1	3.125 (4)	C7···H2	2.5500
O3···C16	3.348 (4)	C8···H18	3.0900
O3···O1ii	3.219 (3)	C8···H5	2.7400
O3···O2	3.155 (3)	C9···H18	2.5300
O3···N1	3.129 (3)	C10···H1	2.8000
O4···C15iii	3.239 (5)	C11···H5	3.0700
O4···C16iii	3.164 (5)	C15···H21ix	2.9200
O5···C12iv	3.414 (5)	C18···H9	2.6400
O2···H7Av	2.8500	C18···H12	2.9500
O2···H19vi	2.6800	C20···H4ii	3.0800
O2···H2v	2.5900	C21···H4ii	3.0800
O2···H1	2.5300	C22···H22ix	3.0600
O4···H12	2.4100	H1···O2	2.5300
O4···H16iii	2.5200	H1···C10	2.8000
O4···H15iii	2.6900	H2···C7	2.5500
O5···H14	2.4200	H2···H7A	2.3200
O5···H5iv	2.6200	H2···H7C	2.3800
N1···O3	3.129 (3)	H2···O2v	2.5900
N1···H16	2.5500	H4···C20i	3.0800
C1···O2	3.125 (4)	H4···C21i	3.0800
C5···C10vii	3.541 (4)	H5···C8	2.7400
C5···C11	3.524 (4)	H5···C11	3.0700
C6···C9vii	3.562 (4)	H5···H8	2.5800
C6···C16	3.432 (4)	H5···O5iv	2.6200
C6···C10vii	3.585 (5)	H7A···C2	2.7600
C7···C7viii	3.533 (6)	H7A···H2	2.3200
C8···C18	3.440 (5)	H7A···O2v	2.8500
C9···C6vii	3.562 (4)	H7A···H7Bviii	2.5800
C10···C6vii	3.585 (5)	H7B···H7Aviii	2.5800
C10···C5vii	3.541 (4)	H7C···C2	2.8000
C10···C16	3.539 (4)	H7C···H2	2.3800
C11···C17	3.234 (5)	H8···C5	3.0800
C11···C5	3.524 (4)	H8···H5	2.5800
C12···C18	3.307 (5)	H8···H12	2.5100
C12···C17	3.280 (5)	H9···C18	2.6400
C12···O5iv	3.414 (5)	H9···H18	2.1200
C13···C13iv	3.477 (5)	H9···C1vii	2.8600
C15···C21ix	3.567 (5)	H9···C2vii	2.8700
C15···O4vi	3.239 (5)	H9···C3vii	2.9100
C16···O3	3.348 (4)	H9···C4vii	2.9500
C16···C6	3.432 (4)	H9···C5vii	2.9400
C16···C10	3.539 (4)	H9···C6vii	2.8900
C16···O4vi	3.164 (5)	H12···O4	2.4100
C17···C12	3.280 (5)	H12···C18	2.9500
C17···O1ii	3.234 (4)	H12···H8	2.5100
C17···C11	3.234 (5)	H14···O5	2.4200
C18···C8	3.440 (5)	H14···C2x	3.0200
C18···C12	3.307 (5)	H14···C3x	2.8900
C21···C15ix	3.567 (5)	H15···O4vi	2.6900
C22···O1ii	3.414 (4)	H16···O4vi	2.5200
C1···H9vii	2.8600	H16···N1	2.5500
C2···H7C	2.8000	H16···C6	2.9200
C2···H18vii	2.9800	H18···C8	3.0900
C2···H14x	3.0200	H18···C9	2.5300
C2···H9vii	2.8700	H18···H9	2.1200
C2···H7A	2.7600	H18···C2vii	2.9800
C3···H14x	2.8900	H19···O2iii	2.6800
C3···H9vii	2.9100	H21···C15ix	2.9200
C4···H9vii	2.9500	H22···C22ix	3.0600
C3—O1—C7	118.6 (3)	C19—C20—C21	119.7 (4)
C9—O3—C17	116.9 (3)	C20—C21—C22	120.5 (4)
C6—N1—C8	130.9 (2)	C17—C22—C21	119.8 (4)
C6—N1—C10	133.3 (3)	C2—C1—H1	120.00
C8—N1—C10	95.8 (2)	C6—C1—H1	120.00
O4—N2—O5	123.3 (4)	C1—C2—H2	120.00
O4—N2—C13	118.4 (3)	C3—C2—H2	120.00
O5—N2—C13	118.2 (3)	C3—C4—H4	120.00
C2—C1—C6	119.9 (3)	C5—C4—H4	120.00
C1—C2—C3	120.4 (3)	C4—C5—H5	120.00
O1—C3—C2	125.4 (3)	C6—C5—H5	120.00
O1—C3—C4	115.2 (3)	O1—C7—H7A	109.00
C2—C3—C4	119.4 (3)	O1—C7—H7B	109.00
C3—C4—C5	120.5 (3)	O1—C7—H7C	109.00
C4—C5—C6	119.9 (3)	H7A—C7—H7B	109.00
N1—C6—C1	120.6 (3)	H7A—C7—H7C	110.00
N1—C6—C5	119.6 (3)	H7B—C7—H7C	109.00
C1—C6—C5	119.9 (3)	N1—C8—H8	112.00
N1—C8—C9	86.1 (2)	C9—C8—H8	112.00
N1—C8—C11	115.7 (2)	C11—C8—H8	112.00
C9—C8—C11	115.3 (3)	O3—C9—H9	113.00
O3—C9—C8	116.7 (3)	C8—C9—H9	113.00
O3—C9—C10	112.6 (3)	C10—C9—H9	113.00
C8—C9—C10	85.8 (2)	C11—C12—H12	120.00
O2—C10—N1	131.9 (3)	C13—C12—H12	120.00
O2—C10—C9	135.9 (3)	C13—C14—H14	121.00
N1—C10—C9	92.2 (3)	C15—C14—H14	121.00
C8—C11—C12	119.8 (3)	C14—C15—H15	120.00
C8—C11—C16	121.9 (3)	C16—C15—H15	120.00
C12—C11—C16	118.2 (2)	C11—C16—H16	119.00
C11—C12—C13	119.5 (3)	C15—C16—H16	119.00
N2—C13—C12	118.7 (3)	C17—C18—H18	120.00
N2—C13—C14	118.7 (3)	C19—C18—H18	120.00
C12—C13—C14	122.5 (3)	C18—C19—H19	120.00
C13—C14—C15	118.3 (3)	C20—C19—H19	120.00
C14—C15—C16	120.2 (3)	C19—C20—H20	120.00
C11—C16—C15	121.4 (3)	C21—C20—H20	120.00
O3—C17—C18	124.4 (3)	C20—C21—H21	120.00
O3—C17—C22	115.6 (3)	C22—C21—H21	120.00
C18—C17—C22	120.0 (4)	C17—C22—H22	120.00
C17—C18—C19	119.3 (3)	C21—C22—H22	120.00
C18—C19—C20	120.7 (4)
C7—O1—C3—C4	−177.8 (3)	C4—C5—C6—N1	178.3 (3)
C7—O1—C3—C2	2.1 (5)	C9—C8—C11—C12	92.0 (4)
C17—O3—C9—C10	−177.7 (3)	N1—C8—C11—C16	15.1 (4)
C9—O3—C17—C22	168.1 (3)	N1—C8—C11—C12	−169.7 (3)
C17—O3—C9—C8	−80.8 (3)	N1—C8—C9—O3	−116.3 (3)
C9—O3—C17—C18	−10.9 (4)	N1—C8—C9—C10	−3.0 (2)
C6—N1—C10—O2	−4.2 (6)	C9—C8—C11—C16	−83.2 (4)
C6—N1—C8—C9	−173.9 (3)	C11—C8—C9—O3	0.4 (4)
C10—N1—C8—C9	3.4 (2)	C11—C8—C9—C10	113.7 (3)
C8—N1—C6—C1	−172.3 (2)	C8—C9—C10—N1	3.2 (2)
C8—N1—C10—O2	178.7 (4)	C8—C9—C10—O2	−179.0 (4)
C8—N1—C10—C9	−3.4 (2)	O3—C9—C10—N1	120.5 (3)
C8—N1—C6—C5	8.2 (4)	O3—C9—C10—O2	−61.8 (5)
C10—N1—C8—C11	−113.0 (3)	C12—C11—C16—C15	0.2 (5)
C6—N1—C8—C11	69.8 (4)	C16—C11—C12—C13	1.5 (5)
C10—N1—C6—C5	−168.0 (3)	C8—C11—C16—C15	175.4 (3)
C6—N1—C10—C9	173.7 (3)	C8—C11—C12—C13	−173.9 (3)
C10—N1—C6—C1	11.5 (4)	C11—C12—C13—N2	176.8 (3)
O5—N2—C13—C12	177.9 (3)	C11—C12—C13—C14	−1.5 (5)
O4—N2—C13—C14	176.2 (3)	N2—C13—C14—C15	−178.4 (3)
O5—N2—C13—C14	−3.8 (5)	C12—C13—C14—C15	−0.2 (5)
O4—N2—C13—C12	−2.2 (5)	C13—C14—C15—C16	1.8 (5)
C2—C1—C6—N1	−178.1 (2)	C14—C15—C16—C11	−1.8 (5)
C2—C1—C6—C5	1.4 (4)	O3—C17—C18—C19	178.8 (3)
C6—C1—C2—C3	−0.6 (4)	C22—C17—C18—C19	−0.1 (5)
C1—C2—C3—O1	179.6 (3)	O3—C17—C22—C21	−178.1 (3)
C1—C2—C3—C4	−0.5 (5)	C18—C17—C22—C21	1.0 (5)
O1—C3—C4—C5	−179.4 (3)	C17—C18—C19—C20	−0.6 (6)
C2—C3—C4—C5	0.8 (5)	C18—C19—C20—C21	0.4 (6)
C3—C4—C5—C6	0.1 (5)	C19—C20—C21—C22	0.5 (6)
C4—C5—C6—C1	−1.2 (4)	C20—C21—C22—C17	−1.2 (6)

Cg2 and Cg4 are the centroids of the C1–C6 and C17–C22 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2	0.93	2.53	3.125 (4)	122
C2—H2···O2v	0.93	2.59	3.464 (4)	156
C16—H16···O4vi	0.93	2.52	3.164 (5)	126
C16—H16···N1	0.93	2.55	2.898 (3)	103
C4—H4···Cg4i	0.93	2.89	3.716 (4)	149
C9—H9···Cg2vii	0.98	2.55	3.463 (4)	154

	Ring 2	Ring 3	Ring 4
Ring 1	11.61 (19)	74.5 (2)	72.3 (2)
Ring 2		84.98 (15)	60.96 (16)
Ring 3			36.22 (17)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C1–C6 and C17–C22 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2	0.93	2.53	3.125 (4)	122
C2—H2⋯O2i	0.93	2.59	3.464 (4)	156
C16—H16⋯O4ii	0.93	2.52	3.164 (5)	126
C4—H4⋯Cg4iii	0.93	2.89	3.716 (4)	149
C9—H9⋯Cg2iv	0.98	2.55	3.463 (4)	154

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