N-[(E)-1,3-Benzodioxol-5-yl-methyl-idene]-4-methyl-aniline.

The two symmetry-independent mol-ecules in the asymmetric unit of the title compound, C(15)H(13)NO(2), differ in conformation, with the virtually planar 4-methyl-aniline (r.m.s. deviations of 0.0511 and 0.0082 Å) and piperonal groups (r.m.s. deviations of 0.0241 and 0.0486 Å) forming dihedral angles of 19.40 (5) and 42.90 (6)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯π inter-actions. The H atoms of the two methyl groups are disordered over two sets of sites of equal occupancy.

Related literature

For background to our ongoing project on the synthesis of various Schiff bases of piperonal and then their metal complexation and for a related structure, see: Tahir et al. (2010 ▶).

Experimental

Crystal data

C15H13NO2

M = 239.26

Triclinic,

a = 10.6914 (4) Å

b = 10.7680 (3) Å

c = 13.3332 (5) Å

α = 89.443 (2)°

β = 67.112 (2)°

γ = 62.534 (1)°

V = 1227.41 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.32 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.988

18069 measured reflections

4417 independent reflections

3294 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.03

4417 reflections

323 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048038/gk2324sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048038/gk2324Isup2.hkl

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

C15H13NO2	Z = 4
Mr = 239.26	F(000) = 504
Triclinic, P1	Dx = 1.295 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6914 (4) Å	Cell parameters from 3294 reflections
b = 10.7680 (3) Å	θ = 2.2–25.3°
c = 13.3332 (5) Å	µ = 0.09 mm−1
α = 89.443 (2)°	T = 296 K
β = 67.112 (2)°	Prisms, yellow
γ = 62.534 (1)°	0.32 × 0.22 × 0.18 mm
V = 1227.41 (8) Å3

Bruker Kappa APEXII CCD diffractometer	4417 independent reflections
Radiation source: fine-focus sealed tube	3294 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 8.20 pixels mm-1	θmax = 25.3°, θmin = 2.8°
ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
Tmin = 0.980, Tmax = 0.988	l = −16→16
18069 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.050P)2 + 0.2009P] where P = (Fo2 + 2Fc2)/3
4417 reflections	(Δ/σ)max < 0.001
323 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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 esds are taken into account in the estimation of distances, angles and torsion angles

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)
O1	0.85323 (13)	0.05174 (12)	0.16217 (13)	0.0823 (5)
O2	0.84925 (13)	−0.15617 (11)	0.13086 (10)	0.0649 (4)
N1	0.27161 (15)	0.46441 (13)	0.35889 (10)	0.0525 (4)
C1	0.12804 (17)	0.59481 (15)	0.39573 (12)	0.0479 (5)
C2	0.10114 (18)	0.70402 (16)	0.46908 (13)	0.0545 (5)
C3	−0.0303 (2)	0.83722 (17)	0.50051 (14)	0.0594 (6)
C4	−0.1380 (2)	0.86823 (17)	0.45801 (14)	0.0603 (6)
C5	−0.1111 (2)	0.75802 (19)	0.38577 (16)	0.0702 (7)
C6	0.0193 (2)	0.62326 (18)	0.35508 (15)	0.0649 (6)
C7	−0.27620 (18)	1.01681 (13)	0.48639 (16)	0.0868 (8)
C8	0.27767 (15)	0.34643 (13)	0.33754 (12)	0.0518 (5)
C9	0.42524 (17)	0.21151 (15)	0.28682 (12)	0.0476 (5)
C10	0.56824 (18)	0.20906 (15)	0.25598 (13)	0.0527 (5)
C11	0.70124 (18)	0.08074 (16)	0.20435 (13)	0.0512 (5)
C12	0.69907 (18)	−0.04387 (14)	0.18398 (12)	0.0481 (5)
C13	0.56266 (19)	−0.04509 (16)	0.21265 (13)	0.0547 (6)
C14	0.42526 (19)	0.08612 (16)	0.26411 (13)	0.0534 (6)
C15	0.9484 (2)	−0.09882 (17)	0.12271 (18)	0.0729 (7)
O3	−0.35490 (13)	1.45856 (11)	0.39324 (10)	0.0723 (4)
O4	−0.34615 (13)	1.64734 (11)	0.31303 (10)	0.0668 (4)
N2	0.18413 (14)	1.00194 (12)	0.16824 (10)	0.0483 (4)
C16	0.31939 (16)	0.86467 (14)	0.12541 (12)	0.0431 (5)
C17	0.43932 (17)	0.81718 (16)	0.01782 (12)	0.0513 (5)
C18	0.56401 (18)	0.67969 (17)	−0.01516 (13)	0.0544 (5)
C19	0.57678 (17)	0.58422 (15)	0.05568 (13)	0.0499 (5)
C20	0.45610 (19)	0.63169 (16)	0.16171 (14)	0.0563 (6)
C21	0.32925 (18)	0.76868 (16)	0.19582 (13)	0.0532 (5)
C22	0.71353 (14)	0.43394 (12)	0.01711 (12)	0.0656 (6)
C23	0.18014 (14)	1.10785 (12)	0.12391 (11)	0.0479 (5)
C24	0.04255 (17)	1.25022 (14)	0.16788 (12)	0.0439 (5)
C25	−0.09113 (17)	1.27386 (15)	0.26267 (12)	0.0485 (5)
C26	−0.21271 (17)	1.40978 (15)	0.30257 (12)	0.0486 (5)
C27	−0.20845 (18)	1.52255 (15)	0.25424 (13)	0.0484 (5)
C28	−0.08194 (19)	1.50285 (16)	0.16051 (13)	0.0539 (6)
C29	0.04428 (18)	1.36396 (15)	0.11813 (13)	0.0512 (5)
C30	−0.4330 (2)	1.61064 (18)	0.40804 (17)	0.0795 (7)
H2	0.17288	0.68733	0.49767	0.0655*
H3	−0.04678	0.90784	0.55151	0.0712*
H5	−0.18260	0.77485	0.35692	0.0843*
H6	0.03349	0.55134	0.30662	0.0778*
H7A	−0.29853	1.06796	0.55526	0.1302*	0.500
H7B	−0.36576	1.01018	0.49375	0.1302*	0.500
H7C	−0.25211	1.06673	0.42819	0.1302*	0.500
H7D	−0.31240	1.02862	0.42953	0.1302*	0.500
H7E	−0.24517	1.08640	0.49106	0.1302*	0.500
H7F	−0.35883	1.02984	0.55661	0.1302*	0.500
H8	0.18479	0.34604	0.35484	0.0622*
H10	0.57163	0.29154	0.27028	0.0632*
H13	0.56126	−0.12878	0.19867	0.0656*
H14	0.32993	0.08964	0.28396	0.0640*
H15A	1.00499	−0.14057	0.16709	0.0875*
H15B	1.02381	−0.12057	0.04595	0.0875*
H17	0.43518	0.87851	−0.03190	0.0616*
H18	0.64236	0.64993	−0.08751	0.0653*
H20	0.46038	0.57005	0.21120	0.0676*
H21	0.24912	0.79690	0.26730	0.0638*
H22A	0.80663	0.43643	0.00573	0.0984*	0.500
H22B	0.72685	0.39048	−0.05150	0.0984*	0.500
H22C	0.69426	0.37915	0.07252	0.0984*	0.500
H22D	0.67853	0.36761	0.01210	0.0984*	0.500
H22E	0.75831	0.41356	0.06933	0.0984*	0.500
H22F	0.79090	0.42489	−0.05468	0.0984*	0.500
H23	0.26796	1.09409	0.06129	0.0575*
H25	−0.09608	1.19938	0.29667	0.0582*
H28	−0.08011	1.57831	0.12668	0.0647*
H29	0.13266	1.34664	0.05446	0.0615*
H30A	−0.43932	1.65312	0.47490	0.0954*
H30B	−0.53839	1.64639	0.41559	0.0954*

	U11	U22	U33	U12	U13	U23
O1	0.0454 (7)	0.0472 (7)	0.1337 (12)	−0.0163 (6)	−0.0273 (7)	−0.0082 (7)
O2	0.0563 (7)	0.0391 (6)	0.0825 (8)	−0.0145 (6)	−0.0256 (6)	0.0000 (5)
N1	0.0473 (8)	0.0487 (7)	0.0477 (8)	−0.0166 (6)	−0.0165 (6)	0.0037 (6)
C1	0.0435 (9)	0.0477 (8)	0.0422 (8)	−0.0183 (7)	−0.0143 (7)	0.0074 (7)
C2	0.0507 (10)	0.0553 (9)	0.0512 (9)	−0.0237 (8)	−0.0193 (8)	0.0069 (7)
C3	0.0606 (11)	0.0488 (9)	0.0530 (10)	−0.0229 (9)	−0.0151 (9)	0.0045 (7)
C4	0.0546 (10)	0.0490 (9)	0.0536 (10)	−0.0149 (8)	−0.0149 (8)	0.0145 (8)
C5	0.0645 (12)	0.0657 (11)	0.0755 (12)	−0.0200 (10)	−0.0410 (10)	0.0156 (10)
C6	0.0650 (12)	0.0556 (10)	0.0672 (11)	−0.0195 (9)	−0.0350 (10)	0.0022 (8)
C7	0.0789 (14)	0.0574 (11)	0.0812 (14)	−0.0085 (10)	−0.0263 (11)	0.0199 (10)
C8	0.0470 (9)	0.0536 (9)	0.0472 (9)	−0.0224 (8)	−0.0166 (7)	0.0104 (7)
C9	0.0474 (9)	0.0462 (8)	0.0435 (8)	−0.0203 (7)	−0.0181 (7)	0.0101 (6)
C10	0.0530 (10)	0.0398 (8)	0.0610 (10)	−0.0210 (8)	−0.0232 (8)	0.0034 (7)
C11	0.0450 (9)	0.0452 (8)	0.0600 (10)	−0.0202 (8)	−0.0222 (8)	0.0052 (7)
C12	0.0513 (10)	0.0371 (8)	0.0489 (9)	−0.0164 (7)	−0.0221 (7)	0.0080 (6)
C13	0.0666 (11)	0.0447 (8)	0.0590 (10)	−0.0321 (8)	−0.0276 (9)	0.0141 (7)
C14	0.0527 (10)	0.0549 (9)	0.0563 (10)	−0.0311 (8)	−0.0219 (8)	0.0166 (7)
C15	0.0519 (11)	0.0451 (9)	0.0973 (14)	−0.0146 (9)	−0.0212 (10)	0.0035 (9)
O3	0.0521 (7)	0.0471 (6)	0.0740 (8)	−0.0125 (6)	−0.0016 (6)	0.0077 (6)
O4	0.0593 (7)	0.0405 (6)	0.0775 (8)	−0.0121 (6)	−0.0237 (6)	0.0094 (5)
N2	0.0434 (7)	0.0425 (7)	0.0483 (7)	−0.0166 (6)	−0.0156 (6)	0.0054 (5)
C16	0.0385 (8)	0.0420 (8)	0.0451 (8)	−0.0178 (7)	−0.0172 (7)	0.0047 (6)
C17	0.0473 (9)	0.0499 (9)	0.0474 (9)	−0.0192 (8)	−0.0179 (8)	0.0118 (7)
C18	0.0413 (9)	0.0562 (9)	0.0484 (9)	−0.0171 (8)	−0.0119 (7)	0.0019 (7)
C19	0.0421 (9)	0.0448 (8)	0.0634 (10)	−0.0189 (7)	−0.0267 (8)	0.0049 (7)
C20	0.0604 (11)	0.0469 (9)	0.0606 (10)	−0.0241 (8)	−0.0285 (9)	0.0165 (8)
C21	0.0519 (10)	0.0502 (9)	0.0472 (9)	−0.0233 (8)	−0.0144 (8)	0.0089 (7)
C22	0.0526 (10)	0.0481 (9)	0.0890 (13)	−0.0156 (8)	−0.0355 (10)	0.0026 (8)
C23	0.0456 (9)	0.0484 (8)	0.0440 (8)	−0.0234 (7)	−0.0139 (7)	0.0039 (7)
C24	0.0464 (9)	0.0421 (8)	0.0430 (8)	−0.0214 (7)	−0.0197 (7)	0.0053 (6)
C25	0.0528 (9)	0.0399 (8)	0.0480 (9)	−0.0223 (7)	−0.0182 (8)	0.0091 (6)
C26	0.0445 (9)	0.0436 (8)	0.0481 (9)	−0.0186 (7)	−0.0151 (7)	0.0049 (7)
C27	0.0502 (9)	0.0380 (8)	0.0562 (9)	−0.0179 (7)	−0.0272 (8)	0.0072 (7)
C28	0.0661 (11)	0.0472 (9)	0.0588 (10)	−0.0325 (8)	−0.0315 (9)	0.0190 (7)
C29	0.0535 (10)	0.0519 (9)	0.0485 (9)	−0.0302 (8)	−0.0173 (8)	0.0101 (7)
C30	0.0655 (12)	0.0465 (10)	0.0794 (13)	−0.0093 (9)	−0.0105 (10)	0.0069 (9)

O1—C11	1.371 (3)	C8—H8	0.9300
O1—C15	1.421 (2)	C10—H10	0.9300
O2—C12	1.372 (2)	C13—H13	0.9300
O2—C15	1.425 (3)	C14—H14	0.9300
O3—C26	1.377 (2)	C15—H15B	0.9700
O3—C30	1.426 (2)	C15—H15A	0.9700
O4—C27	1.373 (2)	C16—C17	1.394 (2)
O4—C30	1.427 (2)	C16—C21	1.385 (2)
N1—C1	1.417 (2)	C17—C18	1.378 (2)
N1—C8	1.271 (2)	C18—C19	1.386 (2)
N2—C16	1.416 (2)	C19—C20	1.383 (2)
N2—C23	1.2702 (17)	C19—C22	1.507 (2)
C1—C2	1.383 (2)	C20—C21	1.382 (2)
C1—C6	1.378 (3)	C23—C24	1.458 (2)
C2—C3	1.379 (2)	C24—C25	1.404 (2)
C3—C4	1.381 (3)	C24—C29	1.391 (2)
C4—C5	1.382 (3)	C25—C26	1.355 (2)
C4—C7	1.511 (2)	C26—C27	1.380 (2)
C5—C6	1.385 (3)	C27—C28	1.365 (3)
C8—C9	1.460 (2)	C28—C29	1.392 (2)
C9—C10	1.408 (3)	C17—H17	0.9300
C9—C14	1.387 (2)	C18—H18	0.9300
C10—C11	1.360 (2)	C20—H20	0.9300
C11—C12	1.384 (2)	C21—H21	0.9300
C12—C13	1.363 (3)	C22—H22A	0.9600
C13—C14	1.395 (2)	C22—H22B	0.9600
C2—H2	0.9300	C22—H22C	0.9600
C3—H3	0.9300	C22—H22D	0.9600
C5—H5	0.9300	C22—H22E	0.9600
C6—H6	0.9300	C22—H22F	0.9600
C7—H7D	0.9600	C23—H23	0.9300
C7—H7E	0.9600	C25—H25	0.9300
C7—H7A	0.9600	C28—H28	0.9300
C7—H7B	0.9600	C29—H29	0.9300
C7—H7C	0.9600	C30—H30A	0.9700
C7—H7F	0.9600	C30—H30B	0.9700
C11—O1—C15	106.38 (15)	O2—C15—H15A	110.00
C12—O2—C15	105.90 (13)	O2—C15—H15B	110.00
C26—O3—C30	105.62 (14)	O1—C15—H15A	110.00
C27—O4—C30	105.60 (12)	N2—C16—C17	125.51 (13)
C1—N1—C8	120.32 (17)	N2—C16—C21	116.66 (14)
C16—N2—C23	121.55 (14)	C17—C16—C21	117.79 (14)
N1—C1—C2	118.47 (17)	C16—C17—C18	120.24 (14)
N1—C1—C6	123.39 (15)	C17—C18—C19	122.32 (15)
C2—C1—C6	117.89 (16)	C18—C19—C20	116.99 (15)
C1—C2—C3	121.09 (19)	C18—C19—C22	121.24 (14)
C2—C3—C4	121.56 (17)	C20—C19—C22	121.74 (14)
C3—C4—C5	116.92 (17)	C19—C20—C21	121.48 (15)
C5—C4—C7	121.5 (2)	C16—C21—C20	121.15 (15)
C3—C4—C7	121.57 (17)	N2—C23—C24	122.21 (14)
C4—C5—C6	121.9 (2)	C23—C24—C25	119.96 (13)
C1—C6—C5	120.59 (18)	C23—C24—C29	120.34 (15)
N1—C8—C9	122.35 (17)	C25—C24—C29	119.68 (14)
C8—C9—C10	120.28 (15)	C24—C25—C26	117.21 (14)
C8—C9—C14	119.97 (18)	O3—C26—C25	127.71 (14)
C10—C9—C14	119.68 (15)	O3—C26—C27	109.61 (13)
C9—C10—C11	117.06 (16)	C25—C26—C27	122.69 (16)
O1—C11—C12	109.29 (15)	O4—C27—C26	109.96 (15)
O1—C11—C10	128.18 (17)	O4—C27—C28	128.39 (14)
C10—C11—C12	122.5 (2)	C26—C27—C28	121.64 (15)
O2—C12—C11	109.89 (17)	C27—C28—C29	116.57 (15)
O2—C12—C13	128.21 (15)	C24—C29—C28	122.18 (16)
C11—C12—C13	121.88 (15)	O3—C30—O4	108.15 (15)
C12—C13—C14	116.30 (17)	C16—C17—H17	120.00
C9—C14—C13	122.6 (2)	C18—C17—H17	120.00
O1—C15—O2	108.12 (17)	C17—C18—H18	119.00
C1—C2—H2	119.00	C19—C18—H18	119.00
C3—C2—H2	119.00	C19—C20—H20	119.00
C2—C3—H3	119.00	C21—C20—H20	119.00
C4—C3—H3	119.00	C16—C21—H21	119.00
C4—C5—H5	119.00	C20—C21—H21	119.00
C6—C5—H5	119.00	C19—C22—H22A	109.00
C5—C6—H6	120.00	C19—C22—H22B	109.00
C1—C6—H6	120.00	C19—C22—H22C	109.00
C4—C7—H7A	109.00	C19—C22—H22D	109.00
C4—C7—H7B	109.00	C19—C22—H22E	109.00
C4—C7—H7C	109.00	C19—C22—H22F	109.00
H7A—C7—H7B	109.00	H22A—C22—H22B	109.00
H7A—C7—H7C	109.00	H22A—C22—H22C	109.00
H7A—C7—H7D	141.00	H22A—C22—H22D	141.00
H7A—C7—H7E	56.00	H22A—C22—H22E	56.00
H7A—C7—H7F	56.00	H22A—C22—H22F	56.00
H7B—C7—H7C	109.00	H22B—C22—H22C	109.00
H7B—C7—H7D	56.00	H22B—C22—H22D	56.00
H7B—C7—H7E	141.00	H22B—C22—H22E	141.00
H7B—C7—H7F	56.00	H22B—C22—H22F	56.00
H7C—C7—H7D	56.00	H22C—C22—H22D	56.00
H7C—C7—H7E	56.00	H22C—C22—H22E	56.00
H7C—C7—H7F	141.00	H22C—C22—H22F	141.00
H7D—C7—H7E	109.00	H22D—C22—H22E	109.00
H7D—C7—H7F	109.00	H22D—C22—H22F	109.00
H7E—C7—H7F	109.00	H22E—C22—H22F	109.00
C4—C7—H7F	109.00	N2—C23—H23	119.00
C4—C7—H7E	109.00	C24—C23—H23	119.00
C4—C7—H7D	109.00	C24—C25—H25	121.00
N1—C8—H8	119.00	C26—C25—H25	121.00
C9—C8—H8	119.00	C27—C28—H28	122.00
C9—C10—H10	121.00	C29—C28—H28	122.00
C11—C10—H10	121.00	C24—C29—H29	119.00
C12—C13—H13	122.00	C28—C29—H29	119.00
C14—C13—H13	122.00	O3—C30—H30A	110.00
C9—C14—H14	119.00	O3—C30—H30B	110.00
C13—C14—H14	119.00	O4—C30—H30A	110.00
O1—C15—H15B	110.00	O4—C30—H30B	110.00
H15A—C15—H15B	108.00	H30A—C30—H30B	108.00
C15—O1—C11—C10	176.76 (18)	C9—C10—C11—O1	176.83 (16)
C15—O1—C11—C12	−5.02 (19)	C9—C10—C11—C12	−1.2 (2)
C11—O1—C15—O2	6.6 (2)	C10—C11—C12—O2	179.84 (15)
C15—O2—C12—C11	2.67 (18)	C10—C11—C12—C13	1.3 (3)
C15—O2—C12—C13	−178.93 (17)	O1—C11—C12—C13	−177.02 (15)
C12—O2—C15—O1	−5.73 (19)	O1—C11—C12—O2	1.50 (18)
C26—O3—C30—O4	10.3 (2)	O2—C12—C13—C14	−178.49 (15)
C30—O3—C26—C27	−7.0 (2)	C11—C12—C13—C14	−0.3 (2)
C30—O3—C26—C25	173.0 (2)	C12—C13—C14—C9	−0.9 (2)
C27—O4—C30—O3	−9.8 (2)	N2—C16—C17—C18	−178.61 (19)
C30—O4—C27—C28	−175.6 (2)	C21—C16—C17—C18	−1.2 (3)
C30—O4—C27—C26	5.5 (2)	N2—C16—C21—C20	179.60 (19)
C1—N1—C8—C9	172.46 (13)	C17—C16—C21—C20	1.9 (3)
C8—N1—C1—C6	−38.5 (2)	C16—C17—C18—C19	−0.5 (3)
C8—N1—C1—C2	147.31 (16)	C17—C18—C19—C20	1.4 (3)
C16—N2—C23—C24	−179.17 (16)	C17—C18—C19—C22	179.34 (19)
C23—N2—C16—C21	161.80 (18)	C18—C19—C20—C21	−0.6 (3)
C23—N2—C16—C17	−20.7 (3)	C22—C19—C20—C21	−178.55 (19)
N1—C1—C2—C3	174.47 (15)	C19—C20—C21—C16	−1.0 (3)
C2—C1—C6—C5	1.1 (3)	N2—C23—C24—C25	0.4 (3)
N1—C1—C6—C5	−173.16 (17)	N2—C23—C24—C29	178.66 (17)
C6—C1—C2—C3	0.0 (3)	C23—C24—C25—C26	177.07 (17)
C1—C2—C3—C4	−1.8 (3)	C29—C24—C25—C26	−1.2 (3)
C2—C3—C4—C7	−175.81 (17)	C23—C24—C29—C28	−176.98 (18)
C2—C3—C4—C5	2.4 (3)	C25—C24—C29—C28	1.3 (3)
C3—C4—C5—C6	−1.4 (3)	C24—C25—C26—O3	179.66 (18)
C7—C4—C5—C6	176.84 (18)	C24—C25—C26—C27	−0.4 (3)
C4—C5—C6—C1	−0.3 (3)	O3—C26—C27—O4	1.0 (2)
N1—C8—C9—C14	−179.24 (15)	O3—C26—C27—C28	−178.02 (18)
N1—C8—C9—C10	−2.3 (2)	C25—C26—C27—O4	−179.03 (17)
C8—C9—C10—C11	−176.93 (14)	C25—C26—C27—C28	2.0 (3)
C14—C9—C10—C11	0.1 (2)	O4—C27—C28—C29	179.37 (19)
C10—C9—C14—C13	1.0 (2)	C26—C27—C28—C29	−1.9 (3)
C8—C9—C14—C13	177.97 (15)	C27—C28—C29—C24	0.2 (3)

Cg3, Cg5 and Cg6 are the centroids of the C9–C14, C16–C21 and C24–C29 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···O2i	0.93	2.59	3.447 (2)	153
C17—H17···Cg3ii	0.93	2.73	3.5306 (16)	145
C22—H22B···Cg5ii	0.96	2.86	3.5480 (18)	130
C22—H22D···Cg5ii	0.96	2.71	3.5480 (18)	146
C22—H22E···Cg6iii	0.96	2.91	3.8610 (18)	169

Table 1

Hydrogen-bond geometry (Å, °)

Cg3, Cg5 and Cg6 are the centroids of the C9–C14, C16–C21 and C24–C29 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯O2i	0.93	2.59	3.447 (2)	153
C17—H17⋯Cg3ii	0.93	2.73	3.5306 (16)	145
C22—H22B⋯Cg5ii	0.96	2.86	3.5480 (18)	130
C22—H22D⋯Cg5ii	0.96	2.71	3.5480 (18)	146
C22—H22E⋯Cg6iii	0.96	2.91	3.8610 (18)	169

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