3-(3-Bromo-phen-yl)-N-phenyl-oxirane-2-carboxamide.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(15)H(12)BrNO(2). In both mol-ecules, the two benzene rings adopt a cis configuration with respect to the ep-oxy ring. In one mol-ecule, the ep-oxy ring makes dihedral angles of 60.5 (2) and 77.92 (19)° with the two benzene rings; in the other mol-ecule, the values are 61.0 (2) and 81.43 (19)°. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For epoxide-containing compounds used as building blocks in synthesis, see: Diez et al. (2008 ▶); Watanabe et al. (1998 ▶); Zhu & Espenson (1995 ▶). For related structures, see: He (2009 ▶); He & Chen (2009 ▶).

Experimental

Crystal data

C15H12BrNO2

M = 318.17

Monoclinic,

a = 5.5124 (1) Å

b = 11.1975 (2) Å

c = 21.3298 (4) Å

β = 94.405 (2)°

V = 1312.69 (4) Å3

Z = 4

Cu Kα radiation

μ = 4.25 mm−1

T = 295 K

0.36 × 0.34 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.310, T max = 0.362

19177 measured reflections

4142 independent reflections

4027 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.084

S = 1.00

4142 reflections

351 parameters

17 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 1768 Friedel pairs

Flack parameter: 0.016 (18)

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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904584X/xu2663sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904584X/xu2663Isup2.hkl

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

C15H12BrNO2	F(000) = 640
Mr = 318.17	Dx = 1.610 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 15364 reflections
a = 5.5124 (1) Å	θ = 2.1–71.8°
b = 11.1975 (2) Å	µ = 4.25 mm−1
c = 21.3298 (4) Å	T = 295 K
β = 94.405 (2)°	Block, colorless
V = 1312.69 (4) Å3	0.36 × 0.34 × 0.30 mm
Z = 4

Oxford Diffraction Gemini S Ultra diffractometer	4142 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	4027 reflections with I > 2σ(I)
mirror	Rint = 0.048
Detector resolution: 15.9149 pixels mm-1	θmax = 65.1°, θmin = 2.1°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→10
Tmin = 0.310, Tmax = 0.362	l = −25→25
19177 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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0457P)2 + 0.857P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
4142 reflections	Δρmax = 0.67 e Å−3
351 parameters	Δρmin = −0.38 e Å−3
17 restraints	Absolute structure: Flack (1983), 1768 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.016 (18)

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
Br1	0.42656 (10)	0.89013 (4)	0.78262 (2)	0.07080 (18)
Br2	0.99441 (11)	0.66221 (5)	0.71660 (2)	0.07210 (17)
O3	0.7352 (6)	0.2259 (3)	0.52366 (13)	0.0628 (8)
N2	0.8472 (5)	0.3942 (3)	0.42997 (14)	0.0468 (7)
N1	0.6413 (5)	0.6562 (3)	1.07453 (13)	0.0453 (7)
O2	0.7701 (6)	0.4874 (3)	0.98389 (13)	0.0584 (8)
O1	0.2403 (5)	0.6400 (3)	1.05633 (13)	0.0589 (8)
O4	1.2515 (5)	0.3825 (3)	0.44653 (13)	0.0592 (7)
C10	0.6238 (6)	0.7481 (3)	1.12127 (15)	0.0396 (8)
C17	0.9052 (7)	0.4659 (4)	0.63585 (17)	0.0465 (9)
H17	1.0499	0.4344	0.6542	0.056*
C7	0.6277 (7)	0.5369 (4)	0.93584 (17)	0.0457 (9)
H7	0.5752	0.4803	0.9025	0.055*
C25	0.8600 (6)	0.4843 (3)	0.38192 (15)	0.0409 (8)
C13	0.6069 (7)	0.9245 (4)	1.21235 (17)	0.0468 (10)
H13	0.6094	0.9866	1.2413	0.056*
C1	0.6161 (7)	0.8207 (4)	0.84397 (17)	0.0466 (9)
C3	0.9538 (8)	0.8303 (4)	0.90649 (19)	0.0554 (11)
H3	1.0970	0.8678	0.9216	0.066*
C5	0.6970 (6)	0.6577 (4)	0.91201 (15)	0.0410 (7)
C16	0.8251 (7)	0.5765 (4)	0.65623 (18)	0.0489 (9)
C6	0.5555 (7)	0.7099 (4)	0.86780 (17)	0.0453 (9)
H6	0.4130	0.6723	0.8522	0.054*
C8	0.5158 (8)	0.5125 (4)	0.99944 (19)	0.0490 (9)
H8	0.4108	0.4418	0.9993	0.059*
C23	0.9853 (8)	0.2580 (4)	0.50714 (18)	0.0509 (9)
H23	1.0999	0.1910	0.5097	0.061*
C14	0.8076 (7)	0.9150 (4)	1.16933 (18)	0.0528 (10)
H14	0.9326	0.9709	1.1736	0.063*
C4	0.8971 (7)	0.7199 (4)	0.93112 (18)	0.0496 (9)
H4	1.0035	0.6874	0.9625	0.060*
C26	1.0499 (7)	0.4918 (4)	0.33747 (17)	0.0460 (9)
H26	1.1762	0.4365	0.3407	0.055*
C15	0.8182 (6)	0.8273 (3)	1.12322 (17)	0.0459 (9)
H15	0.9432	0.8223	1.0964	0.055*
C11	0.4279 (7)	0.7575 (4)	1.16434 (16)	0.0447 (8)
H11	0.3017	0.7022	1.1608	0.054*
C18	0.7812 (6)	0.4049 (4)	0.59137 (16)	0.0445 (9)
C2	0.8138 (7)	0.8835 (4)	0.86286 (18)	0.0513 (9)
H2	0.8487	0.9581	0.8465	0.062*
C21	0.6217 (8)	0.6303 (4)	0.6342 (2)	0.0601 (12)
H21	0.5726	0.7044	0.6484	0.072*
C27	1.0480 (7)	0.5783 (4)	0.29070 (17)	0.0475 (10)
H27	1.1687	0.5828	0.2627	0.057*
C28	0.8594 (8)	0.6554 (4)	0.28868 (16)	0.0508 (9)
H28	0.8498	0.7151	0.2583	0.061*
C9	0.4518 (7)	0.6102 (4)	1.04614 (16)	0.0444 (8)
C30	0.6630 (6)	0.5628 (4)	0.38105 (18)	0.0490 (9)
H30	0.5425	0.5588	0.4092	0.059*
C29	0.6667 (7)	0.6478 (4)	0.33342 (18)	0.0568 (10)
H29	0.5407	0.7032	0.3294	0.068*
C20	0.4981 (8)	0.5692 (5)	0.5910 (2)	0.0623 (12)
H20	0.3527	0.6011	0.5734	0.075*
C12	0.4244 (7)	0.8461 (4)	1.21031 (16)	0.0505 (11)
H12	0.3019	0.8503	1.2379	0.061*
C24	1.0405 (7)	0.3523 (3)	0.45838 (16)	0.0460 (9)
C19	0.5729 (7)	0.4571 (5)	0.56933 (19)	0.0575 (11)
H19	0.4740	0.4178	0.5386	0.069*
C22	0.8683 (8)	0.2850 (4)	0.57056 (18)	0.0499 (9)
H22	0.9286	0.2333	0.6054	0.060*
H1A	0.779 (4)	0.631 (3)	1.0586 (16)	0.038 (10)*
H2A	0.710 (5)	0.369 (4)	0.4461 (18)	0.055 (12)*

	U11	U22	U33	U12	U13	U23
Br1	0.0567 (3)	0.0843 (4)	0.0696 (3)	0.0040 (3)	−0.00674 (19)	0.0319 (3)
Br2	0.0783 (3)	0.0641 (3)	0.0704 (3)	0.0098 (3)	−0.0172 (2)	−0.0138 (3)
O3	0.079 (2)	0.0537 (18)	0.0527 (16)	−0.0231 (16)	−0.0157 (14)	0.0082 (14)
N2	0.0472 (16)	0.052 (2)	0.0402 (15)	−0.0079 (18)	−0.0066 (12)	0.0116 (15)
N1	0.0473 (16)	0.0487 (19)	0.0381 (14)	0.0032 (17)	−0.0079 (12)	−0.0073 (15)
O2	0.075 (2)	0.0446 (18)	0.0516 (16)	0.0170 (15)	−0.0173 (14)	−0.0015 (12)
O1	0.0532 (16)	0.063 (2)	0.0580 (16)	0.0031 (15)	−0.0148 (13)	−0.0066 (14)
O4	0.0515 (15)	0.0659 (19)	0.0575 (15)	−0.0072 (17)	−0.0142 (12)	0.0116 (16)
C10	0.0419 (18)	0.040 (2)	0.0352 (17)	0.0040 (15)	−0.0104 (14)	0.0030 (15)
C17	0.0401 (18)	0.051 (2)	0.0463 (19)	0.0012 (17)	−0.0063 (15)	0.0068 (18)
C7	0.052 (2)	0.040 (2)	0.0423 (19)	0.0012 (17)	−0.0148 (16)	−0.0033 (16)
C25	0.0436 (18)	0.040 (2)	0.0369 (17)	−0.0055 (16)	−0.0105 (14)	0.0013 (14)
C13	0.056 (2)	0.044 (2)	0.0374 (18)	0.0146 (18)	−0.0198 (16)	−0.0074 (16)
C1	0.0414 (19)	0.053 (2)	0.0445 (18)	0.0058 (17)	−0.0029 (15)	0.0018 (17)
C3	0.051 (2)	0.064 (3)	0.050 (2)	−0.018 (2)	−0.0049 (18)	−0.0047 (19)
C5	0.0401 (17)	0.045 (2)	0.0374 (16)	0.0005 (18)	−0.0034 (13)	−0.0044 (17)
C16	0.046 (2)	0.052 (2)	0.048 (2)	0.0001 (18)	−0.0019 (16)	0.0050 (17)
C6	0.0415 (19)	0.049 (2)	0.0438 (19)	−0.0016 (16)	−0.0088 (15)	0.0017 (16)
C8	0.061 (2)	0.037 (2)	0.047 (2)	−0.0014 (17)	−0.0124 (17)	0.0010 (16)
C23	0.064 (2)	0.039 (2)	0.047 (2)	−0.0017 (18)	−0.0135 (18)	0.0049 (17)
C14	0.045 (2)	0.050 (3)	0.061 (2)	−0.0024 (17)	−0.0171 (17)	−0.0015 (19)
C4	0.042 (2)	0.061 (3)	0.0439 (19)	−0.0022 (18)	−0.0104 (16)	−0.0056 (18)
C26	0.047 (2)	0.047 (2)	0.0424 (19)	0.0085 (17)	−0.0033 (16)	0.0007 (17)
C15	0.0355 (18)	0.052 (2)	0.049 (2)	0.0028 (16)	−0.0054 (15)	0.0000 (17)
C11	0.0435 (19)	0.047 (2)	0.0422 (18)	−0.0048 (16)	−0.0080 (15)	0.0024 (16)
C18	0.0385 (16)	0.053 (2)	0.0408 (17)	−0.0023 (18)	−0.0057 (13)	0.0110 (17)
C2	0.052 (2)	0.050 (2)	0.0514 (19)	−0.007 (2)	0.0005 (16)	−0.0005 (19)
C21	0.054 (2)	0.063 (3)	0.062 (2)	0.014 (2)	−0.003 (2)	0.011 (2)
C27	0.051 (2)	0.058 (3)	0.0344 (18)	−0.0067 (19)	0.0053 (15)	−0.0034 (17)
C28	0.070 (2)	0.041 (2)	0.0371 (17)	−0.005 (2)	−0.0193 (16)	0.0108 (18)
C9	0.054 (2)	0.041 (2)	0.0368 (17)	0.0025 (16)	−0.0072 (16)	0.0011 (15)
C30	0.0352 (18)	0.058 (3)	0.053 (2)	−0.0027 (17)	−0.0036 (15)	0.0046 (18)
C29	0.0449 (19)	0.058 (3)	0.064 (2)	0.005 (2)	−0.0154 (17)	0.008 (2)
C20	0.046 (2)	0.077 (3)	0.063 (3)	0.013 (2)	−0.0062 (19)	0.015 (2)
C12	0.052 (2)	0.066 (3)	0.0327 (17)	0.017 (2)	−0.0002 (15)	0.0021 (17)
C24	0.058 (2)	0.042 (2)	0.0359 (17)	−0.0058 (17)	−0.0065 (16)	0.0031 (15)
C19	0.043 (2)	0.078 (3)	0.049 (2)	−0.002 (2)	−0.0131 (17)	0.013 (2)
C22	0.058 (2)	0.047 (2)	0.0426 (19)	−0.0070 (18)	−0.0147 (17)	0.0087 (17)

Br1—C1	1.788 (4)	C5—C4	1.341 (5)
Br2—C16	1.807 (4)	C16—C21	1.326 (6)
O3—C22	1.365 (5)	C6—H6	0.9300
O3—C23	1.493 (6)	C8—C9	1.539 (6)
N2—C24	1.274 (5)	C8—H8	0.9800
N2—C25	1.444 (5)	C23—C24	1.528 (5)
N2—H2A	0.90 (3)	C23—C22	1.572 (6)
N1—C9	1.275 (5)	C23—H23	0.9800
N1—C10	1.442 (5)	C14—C15	1.395 (5)
N1—H1A	0.90 (3)	C14—H14	0.9300
O2—C7	1.360 (4)	C4—H4	0.9300
O2—C8	1.492 (5)	C26—C27	1.390 (5)
O1—C9	1.248 (5)	C26—H26	0.9300
O4—C24	1.256 (5)	C15—H15	0.9300
C10—C15	1.389 (5)	C11—C12	1.397 (5)
C10—C11	1.474 (5)	C11—H11	0.9300
C17—C18	1.317 (5)	C18—C19	1.341 (5)
C17—C16	1.396 (6)	C18—C22	1.504 (6)
C17—H17	0.9300	C2—H2	0.9300
C7—C5	1.505 (6)	C21—C20	1.298 (7)
C7—C8	1.557 (6)	C21—H21	0.9300
C7—H7	0.9800	C27—C28	1.349 (5)
C25—C30	1.396 (5)	C27—H27	0.9300
C25—C26	1.468 (5)	C28—C29	1.484 (5)
C13—C12	1.333 (6)	C28—H28	0.9300
C13—C14	1.494 (5)	C30—C29	1.393 (5)
C13—H13	0.9300	C30—H30	0.9300
C1—C2	1.333 (5)	C29—H29	0.9300
C1—C6	1.392 (6)	C20—C19	1.411 (7)
C3—C2	1.306 (6)	C20—H20	0.9300
C3—C4	1.388 (6)	C12—H12	0.9300
C3—H3	0.9300	C19—H19	0.9300
C5—C6	1.314 (5)	C22—H22	0.9800
C22—O3—C23	66.6 (3)	C13—C14—H14	118.1
C24—N2—C25	120.7 (3)	C5—C4—C3	123.5 (4)
C24—N2—H2A	113 (3)	C5—C4—H4	118.3
C25—N2—H2A	125 (3)	C3—C4—H4	118.3
C9—N1—C10	121.4 (3)	C27—C26—C25	122.5 (3)
C9—N1—H1A	112 (2)	C27—C26—H26	118.8
C10—N1—H1A	126 (3)	C25—C26—H26	118.8
C7—O2—C8	66.0 (3)	C10—C15—C14	113.3 (3)
C15—C10—N1	112.6 (3)	C10—C15—H15	123.3
C15—C10—C11	122.5 (3)	C14—C15—H15	123.3
N1—C10—C11	124.9 (3)	C12—C11—C10	122.6 (3)
C18—C17—C16	121.7 (4)	C12—C11—H11	118.7
C18—C17—H17	119.2	C10—C11—H11	118.7
C16—C17—H17	119.2	C17—C18—C19	114.2 (4)
O2—C7—C5	118.3 (3)	C17—C18—C22	121.0 (3)
O2—C7—C8	61.1 (3)	C19—C18—C22	124.7 (4)
C5—C7—C8	125.5 (3)	C3—C2—C1	113.5 (4)
O2—C7—H7	113.9	C3—C2—H2	123.2
C5—C7—H7	113.9	C1—C2—H2	123.2
C8—C7—H7	113.9	C20—C21—C16	113.3 (5)
C30—C25—N2	111.6 (3)	C20—C21—H21	123.3
C30—C25—C26	123.2 (3)	C16—C21—H21	123.3
N2—C25—C26	125.1 (3)	C28—C27—C26	115.6 (4)
C12—C13—C14	121.7 (4)	C28—C27—H27	122.2
C12—C13—H13	119.1	C26—C27—H27	122.2
C14—C13—H13	119.1	C27—C28—C29	122.1 (4)
C2—C1—C6	125.0 (4)	C27—C28—H28	119.0
C2—C1—Br1	114.2 (3)	C29—C28—H28	119.0
C6—C1—Br1	120.8 (3)	O1—C9—N1	123.5 (4)
C2—C3—C4	122.6 (4)	O1—C9—C8	124.5 (4)
C2—C3—H3	118.7	N1—C9—C8	112.0 (4)
C4—C3—H3	118.7	C29—C30—C25	112.6 (3)
C6—C5—C4	114.6 (4)	C29—C30—H30	123.7
C6—C5—C7	119.4 (3)	C25—C30—H30	123.7
C4—C5—C7	126.0 (3)	C30—C29—C28	124.0 (4)
C21—C16—C17	124.9 (4)	C30—C29—H29	118.0
C21—C16—Br2	112.8 (3)	C28—C29—H29	118.0
C17—C16—Br2	122.3 (3)	C21—C20—C19	123.4 (4)
C5—C6—C1	120.9 (4)	C21—C20—H20	118.3
C5—C6—H6	119.6	C19—C20—H20	118.3
C1—C6—H6	119.6	C13—C12—C11	116.1 (4)
O2—C8—C9	123.0 (3)	C13—C12—H12	122.0
O2—C8—C7	53.0 (2)	C11—C12—H12	122.0
C9—C8—C7	124.4 (3)	O4—C24—N2	123.9 (4)
O2—C8—H8	114.3	O4—C24—C23	124.0 (4)
C9—C8—H8	114.3	N2—C24—C23	112.1 (4)
C7—C8—H8	114.3	C18—C19—C20	122.5 (4)
O3—C23—C24	124.2 (3)	C18—C19—H19	118.8
O3—C23—C22	52.8 (2)	C20—C19—H19	118.8
C24—C23—C22	124.7 (4)	O3—C22—C18	118.9 (3)
O3—C23—H23	113.9	O3—C22—C23	60.6 (3)
C24—C23—H23	113.9	C18—C22—C23	125.9 (3)
C22—C23—H23	113.9	O3—C22—H22	113.6
C15—C14—C13	123.8 (4)	C18—C22—H22	113.6
C15—C14—H14	118.1	C23—C22—H22	113.6
C9—N1—C10—C15	−148.8 (4)	Br1—C1—C2—C3	−178.3 (3)
C9—N1—C10—C11	33.1 (5)	C17—C16—C21—C20	0.5 (7)
C8—O2—C7—C5	117.1 (4)	Br2—C16—C21—C20	−179.7 (4)
C24—N2—C25—C30	−147.1 (4)	C25—C26—C27—C28	−0.1 (6)
C24—N2—C25—C26	34.9 (5)	C26—C27—C28—C29	−0.1 (6)
O2—C7—C5—C6	−176.6 (4)	C10—N1—C9—O1	−0.2 (6)
C8—C7—C5—C6	−103.5 (4)	C10—N1—C9—C8	−178.9 (3)
O2—C7—C5—C4	4.3 (6)	O2—C8—C9—O1	173.9 (4)
C8—C7—C5—C4	77.4 (5)	C7—C8—C9—O1	109.1 (5)
C18—C17—C16—C21	0.5 (7)	O2—C8—C9—N1	−7.5 (5)
C18—C17—C16—Br2	−179.3 (3)	C7—C8—C9—N1	−72.2 (5)
C4—C5—C6—C1	0.2 (6)	N2—C25—C30—C29	−177.7 (3)
C7—C5—C6—C1	−179.0 (3)	C26—C25—C30—C29	0.3 (5)
C2—C1—C6—C5	−0.6 (6)	C25—C30—C29—C28	−0.5 (6)
Br1—C1—C6—C5	178.7 (3)	C27—C28—C29—C30	0.5 (7)
C7—O2—C8—C9	−110.7 (4)	C16—C21—C20—C19	−0.3 (7)
C5—C7—C8—O2	−105.8 (4)	C14—C13—C12—C11	−2.0 (6)
O2—C7—C8—C9	108.0 (4)	C10—C11—C12—C13	1.4 (6)
C5—C7—C8—C9	2.3 (6)	C25—N2—C24—O4	−1.6 (6)
C22—O3—C23—C24	−110.4 (4)	C25—N2—C24—C23	−179.8 (3)
C12—C13—C14—C15	1.7 (6)	O3—C23—C24—O4	176.9 (4)
C6—C5—C4—C3	−0.3 (6)	C22—C23—C24—O4	111.6 (5)
C7—C5—C4—C3	178.8 (4)	O3—C23—C24—N2	−4.9 (6)
C2—C3—C4—C5	0.9 (7)	C22—C23—C24—N2	−70.1 (5)
C30—C25—C26—C27	0.0 (6)	C17—C18—C19—C20	1.7 (6)
N2—C25—C26—C27	177.7 (4)	C22—C18—C19—C20	179.2 (4)
N1—C10—C15—C14	−178.4 (3)	C21—C20—C19—C18	−0.8 (7)
C11—C10—C15—C14	−0.2 (5)	C23—O3—C22—C18	117.3 (4)
C13—C14—C15—C10	−0.4 (5)	C17—C18—C22—O3	−179.1 (4)
C15—C10—C11—C12	−0.3 (5)	C19—C18—C22—O3	3.5 (6)
N1—C10—C11—C12	177.7 (3)	C17—C18—C22—C23	−106.1 (4)
C16—C17—C18—C19	−1.5 (6)	C19—C18—C22—C23	76.5 (6)
C16—C17—C18—C22	−179.1 (4)	C24—C23—C22—O3	109.5 (4)
C4—C3—C2—C1	−1.1 (6)	O3—C23—C22—C18	−106.1 (4)
C6—C1—C2—C3	1.0 (6)	C24—C23—C22—C18	3.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.90 (3)	2.55 (2)	3.359 (4)	150
N2—H2A···O4ii	0.90 (3)	2.53 (2)	3.332 (4)	148
C3—H3···O2iii	0.93	2.48	3.214 (5)	136
C4—H4···O1i	0.93	2.36	3.277 (5)	167
C19—H19···O4ii	0.93	2.27	3.160 (5)	160
C20—H20···O3iv	0.93	2.51	3.199 (6)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.90 (3)	2.55 (2)	3.359 (4)	150
N2—H2A⋯O4ii	0.90 (3)	2.53 (2)	3.332 (4)	148
C3—H3⋯O2iii	0.93	2.48	3.214 (5)	136
C4—H4⋯O1i	0.93	2.36	3.277 (5)	167
C19—H19⋯O4ii	0.93	2.27	3.160 (5)	160
C20—H20⋯O3iv	0.93	2.51	3.199 (6)	131

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