(Z)-3-(9-Anthryl)-1-(4-chloro­phen­yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

In the title compound, C₂₆H₁₆ClN₃O₃, the dihedral angle between the anthracene mean plane and imidazole ring is 64.75 (2)°. In the crystal, π–π inter­actions between anthracene fragments lead to the formation of stacks of mol­ecules propagating in [100]. The short distance between the carbonyl groups of symmetry-related molecules [C...O = 2.985 (2) Å] indicates the existence of dipole–dipole inter­actions. The crystal packing also exhibits short inter­molecular contacts between the nitro groups and Cl atoms [Cl...O = 3.181 (2) Å].

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.113
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   292.000
            Value of melting point given =     0.000
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C17     ..       2.98 Ang.

Alert level G
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C1     -C14           1.41 Ang.
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        200 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Chalcones or 1,3-diaryl-2-propen-1-ones are natural or synthetic compounds belonging to the flavonoid family (Corrêa et al., 2001). They exhibit different kinds of biological activities, such as antimicrobial, anticancer, antiviral, ant-malarial, anti-inflammatory activities (Daskiewicz et al., 2005; Vogel et al., 2008; Sivakumar et al., 2009). Hence, chalcones are considered as a class of important therapeutic potentials. The title compound, (I), is part of our effort in order to contribute this research, and we report its crystal structure here.

In (I) (Fig. 1), the dihedral angle between the anthracene and imidazole rings is 64.75 (2)° and the nitroimidazole is slightly twisted away from the 4-chlorophenyl ring with a dihedral angle of 11.55 (2)°. In the crystal, the π-π interactions between the anthracene fragments (Table 1) lead to formation of stacks of the molecules propagated in direction [100]. The short distance between the carbonyl groups [C17···O1(1-x, 2-y, -z) 2.985 (2) Å] (Table 1) reveals an existence of dipole-dipole interactions. The crystal packing also exhibits short intermolecular contacts between the nitro groups and chlorine atoms [Cl···O 3.181 (2) Å] (Table 1).

Related literature

For general background, see: Corrêa et al. (2001); Daskiewicz et al. (2005); Sivakumar et al. (2009); Vogel et al. (2008). The synthesis was described by Erhardt et al. (1985).

S2. Experimental

Compound (I) was synthesized according to the procedure of Erhardt et al. (1985). A crystal of (I) suitable for X-ray analysis was grown from a mixture solution of chloroform and acetone by slow evaporation at room temperature.

S3. Refinement

All the hydrogen atoms were placed at their geometrical positions with C—H = 0.93Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures

Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids.

(Z)-3-(9-Anthryl)-1-(4-chlorophenyl)-2-(4-nitro-1H- imidazol-1-yl)prop-2-en-1-one

Crystal data

C26H16ClN3O3	Z = 2
Mr = 453.87	F(000) = 468
Triclinic, P1	Dx = 1.427 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0511 (9) Å	Cell parameters from 2837 reflections
b = 11.0406 (12) Å	θ = 1.4–25.3°
c = 12.9274 (14) Å	µ = 0.22 mm^−1
α = 76.065 (2)°	T = 292 K
β = 85.974 (2)°	Block, orange
γ = 71.258 (2)°	0.16 × 0.12 × 0.10 mm
V = 1056.1 (2) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4070 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	3354 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
0.3° wide ω exposures scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −9→9
Tmin = 0.956, Tmax = 0.979	k = −13→10
6168 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0441P)^2 + 0.4068P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4070 reflections	Δρmax = 0.56 e Å^−3
299 parameters	Δρmin = −0.50 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.138 (5)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4503 (2)	0.91044 (16)	0.38505 (12)	0.0381 (4)
C2	0.3150 (2)	0.99845 (18)	0.43057 (13)	0.0427 (4)
C3	0.2324 (3)	1.13103 (19)	0.37653 (16)	0.0532 (5)
H3	0.2673	1.1618	0.3078	0.064*
C4	0.1039 (3)	1.2135 (2)	0.4233 (2)	0.0690 (6)
H4	0.0521	1.2999	0.3863	0.083*
C5	0.0482 (3)	1.1702 (3)	0.5267 (2)	0.0758 (7)
H5	−0.0389	1.2284	0.5581	0.091*
C6	0.1195 (3)	1.0455 (3)	0.58072 (18)	0.0671 (6)
H6	0.0806	1.0181	0.6491	0.080*
C7	0.2544 (2)	0.9537 (2)	0.53486 (14)	0.0507 (5)
C8	0.3284 (3)	0.8240 (2)	0.58804 (14)	0.0570 (5)
H8	0.2870	0.7948	0.6553	0.068*
C9	0.4618 (3)	0.7360 (2)	0.54475 (14)	0.0528 (5)
C10	0.5404 (4)	0.6035 (2)	0.60138 (18)	0.0751 (7)
H10	0.4981	0.5739	0.6682	0.090*
C11	0.6738 (4)	0.5211 (2)	0.5604 (2)	0.0864 (8)
H11	0.7210	0.4345	0.5983	0.104*
C12	0.7438 (4)	0.5643 (2)	0.45999 (19)	0.0730 (7)
H12	0.8385	0.5065	0.4332	0.088*
C13	0.6736 (3)	0.68926 (18)	0.40237 (15)	0.0516 (5)
H13	0.7218	0.7164	0.3368	0.062*
C14	0.5276 (2)	0.77936 (17)	0.44076 (13)	0.0428 (4)
C15	0.5225 (2)	0.96316 (15)	0.28220 (12)	0.0370 (4)
H15	0.5605	1.0348	0.2804	0.044*
C16	0.5410 (2)	0.92308 (15)	0.19171 (12)	0.0351 (4)
C17	0.6425 (2)	0.97302 (15)	0.10011 (12)	0.0364 (4)
C18	0.6982 (2)	1.08892 (16)	0.10310 (12)	0.0372 (4)
C19	0.5813 (2)	1.21059 (17)	0.10958 (14)	0.0442 (4)
H19	0.4615	1.2227	0.1122	0.053*
C20	0.6414 (3)	1.31410 (18)	0.11219 (15)	0.0503 (5)
H20	0.5631	1.3961	0.1153	0.060*
C21	0.8197 (3)	1.29305 (19)	0.11011 (15)	0.0532 (5)
C22	0.9379 (3)	1.1743 (2)	0.10195 (16)	0.0563 (5)
H22	1.0576	1.1626	0.0995	0.068*
C23	0.8762 (2)	1.07254 (18)	0.09746 (15)	0.0474 (4)
H23	0.9550	0.9922	0.0906	0.057*
C24	0.5604 (3)	0.70649 (17)	0.15237 (15)	0.0488 (4)
H24	0.6791	0.6812	0.1360	0.059*
C25	0.2993 (3)	0.70981 (18)	0.17933 (14)	0.0480 (4)
C26	0.3024 (2)	0.82478 (17)	0.19785 (13)	0.0425 (4)
H26	0.2098	0.8902	0.2183	0.051*
Cl1	0.90255 (10)	1.41713 (6)	0.11994 (6)	0.0886 (3)
N1	0.47212 (18)	0.82266 (13)	0.17975 (10)	0.0378 (3)
N2	0.4588 (2)	0.63534 (15)	0.15188 (13)	0.0554 (4)
N3	0.1473 (3)	0.6670 (2)	0.18554 (14)	0.0685 (5)
O1	0.68863 (17)	0.91581 (12)	0.02841 (10)	0.0486 (3)
O2	0.0083 (3)	0.7406 (2)	0.21193 (17)	0.0925 (6)
O3	0.1648 (3)	0.5612 (2)	0.16539 (18)	0.1061 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0429 (9)	0.0474 (9)	0.0326 (8)	−0.0239 (7)	−0.0008 (7)	−0.0116 (7)
C2	0.0408 (9)	0.0578 (11)	0.0399 (9)	−0.0234 (8)	0.0005 (7)	−0.0200 (8)
C3	0.0511 (11)	0.0579 (12)	0.0554 (11)	−0.0168 (9)	−0.0008 (9)	−0.0223 (9)
C4	0.0561 (13)	0.0703 (14)	0.0842 (16)	−0.0094 (11)	−0.0040 (11)	−0.0377 (13)
C5	0.0495 (13)	0.108 (2)	0.0832 (17)	−0.0176 (13)	0.0071 (11)	−0.0576 (16)
C6	0.0482 (12)	0.119 (2)	0.0535 (12)	−0.0369 (13)	0.0112 (9)	−0.0440 (13)
C7	0.0441 (10)	0.0823 (14)	0.0407 (9)	−0.0335 (10)	0.0028 (8)	−0.0241 (10)
C8	0.0605 (12)	0.0901 (16)	0.0345 (9)	−0.0445 (12)	0.0046 (8)	−0.0135 (10)
C9	0.0681 (13)	0.0633 (12)	0.0366 (9)	−0.0377 (10)	−0.0063 (8)	−0.0040 (8)
C10	0.113 (2)	0.0690 (15)	0.0459 (12)	−0.0430 (15)	−0.0093 (12)	0.0035 (11)
C11	0.137 (3)	0.0527 (13)	0.0578 (14)	−0.0232 (15)	−0.0204 (15)	0.0063 (11)
C12	0.0934 (18)	0.0528 (12)	0.0627 (14)	−0.0081 (12)	−0.0162 (12)	−0.0099 (10)
C13	0.0619 (12)	0.0490 (10)	0.0441 (10)	−0.0177 (9)	−0.0071 (9)	−0.0085 (8)
C14	0.0505 (10)	0.0486 (10)	0.0365 (9)	−0.0249 (8)	−0.0043 (7)	−0.0089 (7)
C15	0.0408 (9)	0.0366 (8)	0.0385 (8)	−0.0177 (7)	−0.0019 (7)	−0.0091 (7)
C16	0.0384 (9)	0.0322 (8)	0.0376 (8)	−0.0142 (6)	−0.0030 (6)	−0.0083 (6)
C17	0.0361 (8)	0.0373 (8)	0.0358 (8)	−0.0104 (7)	−0.0018 (6)	−0.0092 (7)
C18	0.0439 (9)	0.0390 (8)	0.0318 (8)	−0.0178 (7)	0.0038 (6)	−0.0080 (6)
C19	0.0456 (10)	0.0416 (9)	0.0458 (9)	−0.0154 (8)	0.0034 (7)	−0.0092 (7)
C20	0.0647 (12)	0.0386 (9)	0.0493 (10)	−0.0194 (8)	0.0072 (9)	−0.0107 (8)
C21	0.0713 (13)	0.0516 (11)	0.0508 (11)	−0.0378 (10)	0.0146 (9)	−0.0169 (9)
C22	0.0508 (11)	0.0676 (13)	0.0648 (12)	−0.0333 (10)	0.0149 (9)	−0.0256 (10)
C23	0.0452 (10)	0.0499 (10)	0.0526 (10)	−0.0186 (8)	0.0091 (8)	−0.0195 (8)
C24	0.0616 (12)	0.0385 (9)	0.0507 (10)	−0.0185 (8)	0.0026 (8)	−0.0152 (8)
C25	0.0647 (12)	0.0497 (10)	0.0391 (9)	−0.0343 (9)	−0.0065 (8)	−0.0038 (8)
C26	0.0461 (10)	0.0467 (9)	0.0402 (9)	−0.0221 (8)	−0.0022 (7)	−0.0089 (7)
Cl1	0.1041 (5)	0.0745 (4)	0.1183 (6)	−0.0626 (4)	0.0236 (4)	−0.0392 (4)
N1	0.0449 (8)	0.0364 (7)	0.0372 (7)	−0.0181 (6)	−0.0005 (6)	−0.0107 (6)
N2	0.0803 (12)	0.0435 (9)	0.0524 (9)	−0.0313 (8)	−0.0009 (8)	−0.0133 (7)
N3	0.0902 (15)	0.0785 (13)	0.0566 (10)	−0.0601 (12)	−0.0108 (10)	−0.0030 (9)
O1	0.0552 (8)	0.0524 (7)	0.0465 (7)	−0.0217 (6)	0.0111 (6)	−0.0232 (6)
O2	0.0715 (12)	0.1073 (15)	0.1141 (15)	−0.0560 (11)	0.0001 (11)	−0.0155 (12)
O3	0.1425 (18)	0.1018 (14)	0.1193 (16)	−0.0927 (14)	−0.0026 (13)	−0.0342 (12)

Geometric parameters (Å, º)

C1—C2	1.408 (2)	C15—H15	0.9300
C1—C14	1.408 (2)	C16—N1	1.4318 (19)
C1—C15	1.477 (2)	C16—C17	1.488 (2)
C2—C3	1.421 (3)	C17—O1	1.2162 (19)
C2—C7	1.429 (2)	C17—C18	1.495 (2)
C3—C4	1.355 (3)	C18—C23	1.384 (2)
C3—H3	0.9300	C18—C19	1.389 (2)
C4—C5	1.402 (4)	C19—C20	1.384 (2)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.341 (4)	C20—C21	1.378 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.432 (3)	C21—C22	1.374 (3)
C6—H6	0.9300	C21—Cl1	1.7382 (18)
C7—C8	1.384 (3)	C22—C23	1.380 (3)
C8—C9	1.385 (3)	C22—H22	0.9300
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.425 (3)	C24—N2	1.305 (2)
C9—C14	1.439 (2)	C24—N1	1.369 (2)
C10—C11	1.336 (4)	C24—H24	0.9300
C10—H10	0.9300	C25—C26	1.355 (2)
C11—C12	1.415 (4)	C25—N2	1.360 (3)
C11—H11	0.9300	C25—N3	1.437 (3)
C12—C13	1.357 (3)	C26—N1	1.364 (2)
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.422 (3)	N3—O3	1.219 (3)
C13—H13	0.9300	N3—O2	1.235 (3)
C15—C16	1.330 (2)
C17···O1^i	2.985 (2)	Cg1···Cg2^iii	3.746 (7)
Cl1···O3^ii	3.181 (3)	Cg2···Cg2^iv	3.863 (8)
C2—C1—C14	121.15 (15)	C16—C15—H15	115.3
C2—C1—C15	117.97 (15)	C1—C15—H15	115.3
C14—C1—C15	120.54 (15)	C15—C16—N1	121.23 (14)
C1—C2—C3	122.84 (16)	C15—C16—C17	122.54 (14)
C1—C2—C7	119.41 (17)	N1—C16—C17	116.12 (13)
C3—C2—C7	117.74 (17)	O1—C17—C16	120.77 (14)
C4—C3—C2	121.3 (2)	O1—C17—C18	120.97 (14)
C4—C3—H3	119.4	C16—C17—C18	118.09 (13)
C2—C3—H3	119.4	C23—C18—C19	119.23 (15)
C3—C4—C5	120.8 (2)	C23—C18—C17	117.30 (15)
C3—C4—H4	119.6	C19—C18—C17	123.47 (15)
C5—C4—H4	119.6	C20—C19—C18	120.67 (17)
C6—C5—C4	120.4 (2)	C20—C19—H19	119.7
C6—C5—H5	119.8	C18—C19—H19	119.7
C4—C5—H5	119.8	C21—C20—C19	118.55 (17)
C5—C6—C7	121.2 (2)	C21—C20—H20	120.7
C5—C6—H6	119.4	C19—C20—H20	120.7
C7—C6—H6	119.4	C22—C21—C20	121.89 (17)
C8—C7—C2	119.04 (17)	C22—C21—Cl1	117.65 (16)
C8—C7—C6	122.40 (19)	C20—C21—Cl1	120.45 (15)
C2—C7—C6	118.6 (2)	C21—C22—C23	118.98 (18)
C7—C8—C9	122.41 (17)	C21—C22—H22	120.5
C7—C8—H8	118.8	C23—C22—H22	120.5
C9—C8—H8	118.8	C22—C23—C18	120.63 (17)
C8—C9—C10	121.97 (19)	C22—C23—H23	119.7
C8—C9—C14	119.60 (18)	C18—C23—H23	119.7
C10—C9—C14	118.4 (2)	N2—C24—N1	112.21 (18)
C11—C10—C9	121.4 (2)	N2—C24—H24	123.9
C11—C10—H10	119.3	N1—C24—H24	123.9
C9—C10—H10	119.3	C26—C25—N2	112.81 (16)
C10—C11—C12	120.6 (2)	C26—C25—N3	125.7 (2)
C10—C11—H11	119.7	N2—C25—N3	121.48 (18)
C12—C11—H11	119.7	C25—C26—N1	104.26 (16)
C13—C12—C11	120.5 (2)	C25—C26—H26	127.9
C13—C12—H12	119.7	N1—C26—H26	127.9
C11—C12—H12	119.7	C26—N1—C24	106.95 (14)
C12—C13—C14	121.0 (2)	C26—N1—C16	125.02 (14)
C12—C13—H13	119.5	C24—N1—C16	128.00 (15)
C14—C13—H13	119.5	C24—N2—C25	103.77 (15)
C1—C14—C13	123.55 (16)	O3—N3—O2	124.9 (2)
C1—C14—C9	118.36 (17)	O3—N3—C25	118.1 (2)
C13—C14—C9	118.00 (17)	O2—N3—C25	116.95 (19)
C16—C15—C1	129.36 (14)
C14—C1—C2—C3	−179.34 (15)	C1—C15—C16—C17	−169.86 (16)
C15—C1—C2—C3	7.3 (2)	C15—C16—C17—O1	164.24 (16)
C14—C1—C2—C7	−0.4 (2)	N1—C16—C17—O1	−12.1 (2)
C15—C1—C2—C7	−173.69 (14)	C15—C16—C17—C18	−11.0 (2)
C1—C2—C3—C4	−179.21 (18)	N1—C16—C17—C18	172.64 (13)
C7—C2—C3—C4	1.8 (3)	O1—C17—C18—C23	−54.0 (2)
C2—C3—C4—C5	−0.1 (3)	C16—C17—C18—C23	121.27 (17)
C3—C4—C5—C6	−1.0 (3)	O1—C17—C18—C19	125.09 (18)
C4—C5—C6—C7	0.4 (3)	C16—C17—C18—C19	−59.7 (2)
C1—C2—C7—C8	−1.1 (2)	C23—C18—C19—C20	−1.1 (3)
C3—C2—C7—C8	177.93 (16)	C17—C18—C19—C20	179.92 (15)
C1—C2—C7—C6	178.61 (15)	C18—C19—C20—C21	−1.1 (3)
C3—C2—C7—C6	−2.3 (2)	C19—C20—C21—C22	2.2 (3)
C5—C6—C7—C8	−178.96 (19)	C19—C20—C21—Cl1	−176.77 (14)
C5—C6—C7—C2	1.3 (3)	C20—C21—C22—C23	−1.1 (3)
C2—C7—C8—C9	1.3 (3)	Cl1—C21—C22—C23	177.95 (15)
C6—C7—C8—C9	−178.43 (17)	C21—C22—C23—C18	−1.2 (3)
C7—C8—C9—C10	178.23 (19)	C19—C18—C23—C22	2.2 (3)
C7—C8—C9—C14	0.0 (3)	C17—C18—C23—C22	−178.67 (16)
C8—C9—C10—C11	−177.3 (2)	N2—C25—C26—N1	0.8 (2)
C14—C9—C10—C11	0.9 (3)	N3—C25—C26—N1	−178.49 (16)
C9—C10—C11—C12	1.5 (4)	C25—C26—N1—C24	−0.45 (18)
C10—C11—C12—C13	−1.7 (4)	C25—C26—N1—C16	−178.48 (14)
C11—C12—C13—C14	−0.6 (3)	N2—C24—N1—C26	0.0 (2)
C2—C1—C14—C13	−174.85 (16)	N2—C24—N1—C16	177.96 (15)
C15—C1—C14—C13	−1.7 (2)	C15—C16—N1—C26	53.9 (2)
C2—C1—C14—C9	1.6 (2)	C17—C16—N1—C26	−129.70 (16)
C15—C1—C14—C9	174.79 (14)	C15—C16—N1—C24	−123.73 (19)
C12—C13—C14—C1	179.44 (18)	C17—C16—N1—C24	52.7 (2)
C12—C13—C14—C9	3.0 (3)	N1—C24—N2—C25	0.4 (2)
C8—C9—C14—C1	−1.5 (2)	C26—C25—N2—C24	−0.8 (2)
C10—C9—C14—C1	−179.75 (17)	N3—C25—N2—C24	178.53 (16)
C8—C9—C14—C13	175.20 (17)	C26—C25—N3—O3	179.18 (19)
C10—C9—C14—C13	−3.1 (3)	N2—C25—N3—O3	0.0 (3)
C2—C1—C15—C16	−126.63 (19)	C26—C25—N3—O2	−1.4 (3)
C14—C1—C15—C16	60.0 (2)	N2—C25—N3—O2	179.44 (19)
C1—C15—C16—N1	6.3 (3)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x+1, y+1, z; (iii) −x+1, −y+2, −z+1; (iv) −x, −y+2, −z+1.