Diethyl 3,3'-(phenyl-methyl-ene)bis-(1H-indole-2-carboxyl-ate).

In the title compound, C(29)H(26)N(2)O(4), the benzene ring is twisted by 73.5 (5) and 84.9 (3)° with respect to the mean planes of the two indole ring systems; the mean planes of the indole ring systems are oriented at a dihedral angle of 82.0 (5)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds into chains.

Related literature

For applications of indole derivatives, see: Poter et al. (1977 ▶); Sundberg (1996 ▶); Chang et al. (1999 ▶); Ge et al. (1999 ▶); Ni (2008 ▶).

Experimental

Crystal data

C29H26N2O4

M = 466.52

Triclinic,

a = 8.7340 (17) Å

b = 9.871 (2) Å

c = 15.000 (3) Å

α = 76.14 (3)°

β = 83.91 (3)°

γ = 83.09 (3)°

V = 1242.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4879 measured reflections

4557 independent reflections

2813 reflections with I > 2σ(I)

R int = 0.032

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.144

S = 1.00

4557 reflections

316 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036239/xu5612sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036239/xu5612Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036239/xu5612Isup3.cml

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

C29H26N2O4	Z = 2
Mr = 466.52	F(000) = 492
Triclinic, P1	Dx = 1.247 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7340 (17) Å	Cell parameters from 25 reflections
b = 9.871 (2) Å	θ = 9–13°
c = 15.000 (3) Å	µ = 0.08 mm−1
α = 76.14 (3)°	T = 293 K
β = 83.91 (3)°	Block, colorless
γ = 83.09 (3)°	0.30 × 0.20 × 0.10 mm
V = 1242.4 (4) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.032
Radiation source: fine-focus sealed tube	θmax = 25.4°, θmin = 1.4°
Graphite monochromator	h = 0→10
ω/2θ scans	k = −11→11
4879 measured reflections	l = −17→18
4557 independent reflections	3 standard reflections every 200 reflections
2813 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.068P)2] where P = (Fo2 + 2Fc2)/3
4557 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.33 e Å−3
2 restraints	Δρmin = −0.24 e Å−3

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
N1	0.1091 (2)	1.1102 (2)	0.57403 (13)	0.0464 (5)
H1A	0.0562	1.1030	0.5305	0.056*
O1	0.3652 (2)	0.79594 (18)	0.61548 (14)	0.0671 (6)
C1	0.0036 (3)	1.3484 (3)	0.59245 (18)	0.0543 (7)
H1B	−0.0653	1.3654	0.5469	0.065*
N2	0.3177 (2)	0.6564 (2)	0.93548 (13)	0.0455 (5)
H2A	0.3453	0.5760	0.9700	0.055*
O2	0.1783 (2)	0.8636 (2)	0.51907 (13)	0.0684 (6)
C2	0.0155 (3)	1.4450 (3)	0.64135 (19)	0.0622 (8)
H2B	−0.0449	1.5305	0.6283	0.075*
O3	0.65528 (18)	0.75379 (17)	0.78745 (11)	0.0501 (5)
C3	0.1166 (3)	1.4189 (3)	0.71086 (19)	0.0617 (8)
H3A	0.1214	1.4872	0.7435	0.074*
O4	0.6289 (2)	0.57275 (18)	0.90776 (13)	0.0650 (6)
C4	0.2091 (3)	1.2949 (3)	0.73230 (18)	0.0556 (7)
H4A	0.2753	1.2789	0.7791	0.067*
C5	0.2020 (3)	1.1927 (2)	0.68248 (15)	0.0408 (6)
C6	0.0979 (3)	1.2226 (3)	0.61280 (16)	0.0451 (6)
C7	0.2770 (3)	1.0539 (2)	0.68458 (15)	0.0384 (6)
C8	0.2186 (3)	1.0099 (2)	0.61581 (15)	0.0402 (6)
C9	0.2502 (3)	0.8841 (3)	0.57918 (18)	0.0491 (6)
C10	0.4101 (4)	0.6726 (3)	0.5781 (3)	0.0934 (12)
H10A	0.3348	0.6054	0.6016	0.112*
H10B	0.4081	0.6996	0.5116	0.112*
C11	0.5551 (5)	0.6089 (5)	0.5996 (4)	0.1460 (19)
H11A	0.5781	0.5285	0.5733	0.219*
H11B	0.5575	0.5800	0.6653	0.219*
H11C	0.6308	0.6740	0.5752	0.219*
C12	0.3962 (3)	0.9705 (2)	0.74867 (15)	0.0373 (6)
H12A	0.4708	0.9217	0.7106	0.045*
C13	0.4886 (3)	1.0644 (2)	0.78505 (16)	0.0395 (6)
C14	0.6008 (3)	1.1351 (3)	0.72766 (19)	0.0568 (7)
H14A	0.6244	1.1202	0.6686	0.068*
C15	0.6790 (4)	1.2282 (3)	0.7569 (3)	0.0764 (9)
H15A	0.7541	1.2759	0.7170	0.092*
C16	0.6473 (4)	1.2511 (3)	0.8438 (2)	0.0710 (9)
H16A	0.6991	1.3154	0.8624	0.085*
C17	0.5397 (3)	1.1794 (3)	0.9029 (2)	0.0611 (8)
H17A	0.5190	1.1934	0.9623	0.073*
C18	0.4605 (3)	1.0849 (3)	0.87424 (17)	0.0478 (6)
H18A	0.3882	1.0350	0.9151	0.057*
C19	0.3294 (3)	0.8562 (2)	0.82476 (15)	0.0374 (6)
C20	0.1766 (3)	0.8539 (2)	0.87173 (15)	0.0395 (6)
C21	0.0399 (3)	0.9474 (3)	0.86615 (18)	0.0511 (7)
H21A	0.0363	1.0322	0.8226	0.061*
C22	−0.0862 (3)	0.9119 (3)	0.92517 (19)	0.0619 (8)
H22A	−0.1757	0.9738	0.9214	0.074*
C23	−0.0847 (3)	0.7852 (3)	0.9912 (2)	0.0632 (8)
H23A	−0.1734	0.7642	1.0298	0.076*
C24	0.0448 (3)	0.6912 (3)	1.00012 (17)	0.0527 (7)
H24A	0.0464	0.6071	1.0443	0.063*
C25	0.1743 (3)	0.7277 (2)	0.93981 (16)	0.0426 (6)
C26	0.4107 (3)	0.7330 (2)	0.86766 (15)	0.0388 (6)
C27	0.5734 (3)	0.6772 (2)	0.85723 (16)	0.0402 (6)
C28	0.8177 (3)	0.7041 (3)	0.77442 (18)	0.0553 (7)
H28A	0.8282	0.6102	0.7638	0.066*
H28B	0.8701	0.7019	0.8287	0.066*
C29	0.8863 (3)	0.8028 (3)	0.6932 (2)	0.0802 (10)
H29A	0.9940	0.7727	0.6825	0.120*
H29B	0.8759	0.8952	0.7048	0.120*
H29C	0.8335	0.8044	0.6400	0.120*

	U11	U22	U33	U12	U13	U23
N1	0.0488 (13)	0.0511 (13)	0.0378 (11)	0.0003 (10)	−0.0143 (10)	−0.0049 (10)
O1	0.0723 (14)	0.0525 (12)	0.0859 (14)	0.0166 (10)	−0.0364 (11)	−0.0322 (10)
C1	0.0510 (16)	0.0538 (17)	0.0462 (15)	0.0093 (13)	−0.0099 (13)	0.0071 (13)
N2	0.0469 (13)	0.0359 (11)	0.0461 (12)	0.0014 (10)	−0.0069 (10)	0.0039 (9)
O2	0.0705 (13)	0.0795 (14)	0.0662 (13)	0.0077 (11)	−0.0280 (11)	−0.0355 (11)
C2	0.067 (2)	0.0520 (17)	0.0555 (18)	0.0173 (15)	−0.0037 (15)	−0.0005 (15)
O3	0.0440 (10)	0.0501 (10)	0.0468 (10)	0.0059 (8)	−0.0009 (8)	0.0007 (8)
C3	0.076 (2)	0.0451 (16)	0.0604 (18)	0.0116 (15)	−0.0099 (16)	−0.0114 (13)
O4	0.0580 (12)	0.0507 (11)	0.0675 (12)	0.0134 (9)	−0.0037 (10)	0.0132 (10)
C4	0.0693 (19)	0.0456 (16)	0.0508 (16)	0.0055 (14)	−0.0184 (14)	−0.0086 (13)
C5	0.0446 (14)	0.0399 (14)	0.0320 (13)	0.0002 (11)	−0.0026 (11)	0.0008 (11)
C6	0.0468 (15)	0.0456 (15)	0.0356 (14)	−0.0011 (12)	−0.0037 (11)	0.0032 (11)
C7	0.0397 (13)	0.0400 (13)	0.0317 (12)	0.0015 (11)	−0.0049 (11)	−0.0030 (10)
C8	0.0442 (14)	0.0384 (13)	0.0361 (13)	0.0003 (11)	−0.0100 (11)	−0.0040 (11)
C9	0.0489 (16)	0.0536 (16)	0.0442 (15)	−0.0016 (13)	−0.0104 (13)	−0.0088 (13)
C10	0.098 (3)	0.060 (2)	0.138 (3)	0.0167 (19)	−0.046 (2)	−0.050 (2)
C11	0.123 (4)	0.135 (4)	0.200 (5)	0.021 (3)	−0.042 (4)	−0.082 (4)
C12	0.0407 (14)	0.0348 (13)	0.0353 (13)	0.0057 (11)	−0.0102 (11)	−0.0073 (10)
C13	0.0398 (14)	0.0362 (13)	0.0390 (14)	0.0037 (11)	−0.0102 (11)	−0.0026 (11)
C14	0.0574 (17)	0.0537 (17)	0.0561 (17)	−0.0123 (14)	0.0014 (14)	−0.0055 (14)
C15	0.069 (2)	0.0589 (19)	0.097 (3)	−0.0266 (17)	0.0001 (19)	−0.0023 (18)
C16	0.074 (2)	0.0601 (19)	0.085 (2)	−0.0156 (17)	−0.0234 (19)	−0.0172 (18)
C17	0.074 (2)	0.0598 (18)	0.0549 (17)	−0.0035 (16)	−0.0240 (16)	−0.0178 (15)
C18	0.0524 (16)	0.0494 (15)	0.0412 (15)	−0.0021 (13)	−0.0084 (12)	−0.0090 (12)
C19	0.0405 (14)	0.0338 (13)	0.0363 (13)	0.0004 (11)	−0.0105 (11)	−0.0036 (10)
C20	0.0413 (14)	0.0376 (13)	0.0379 (13)	−0.0032 (11)	−0.0069 (11)	−0.0042 (10)
C21	0.0479 (16)	0.0469 (15)	0.0527 (16)	0.0056 (13)	−0.0080 (13)	−0.0034 (12)
C22	0.0407 (16)	0.0669 (19)	0.070 (2)	0.0074 (14)	0.0033 (15)	−0.0103 (16)
C23	0.0467 (17)	0.071 (2)	0.0633 (19)	−0.0068 (15)	0.0103 (14)	−0.0054 (16)
C24	0.0485 (16)	0.0557 (17)	0.0483 (16)	−0.0087 (14)	−0.0017 (13)	−0.0004 (13)
C25	0.0413 (14)	0.0420 (14)	0.0442 (14)	−0.0024 (12)	−0.0085 (12)	−0.0080 (11)
C26	0.0444 (14)	0.0343 (13)	0.0343 (13)	0.0017 (11)	−0.0066 (11)	−0.0023 (10)
C27	0.0447 (15)	0.0333 (13)	0.0382 (13)	0.0012 (11)	−0.0054 (12)	−0.0014 (11)
C28	0.0501 (17)	0.0554 (17)	0.0543 (17)	0.0047 (13)	0.0025 (13)	−0.0084 (13)
C29	0.065 (2)	0.082 (2)	0.088 (2)	−0.0115 (18)	0.0150 (18)	−0.0142 (19)

N1—C6	1.361 (3)	C12—C13	1.524 (3)
N1—C8	1.375 (3)	C12—H12A	0.9800
N1—H1A	0.8600	C13—C14	1.374 (3)
O1—C9	1.320 (3)	C13—C18	1.392 (3)
O1—C10	1.455 (3)	C14—C15	1.382 (4)
C1—C2	1.354 (4)	C14—H14A	0.9300
C1—C6	1.393 (3)	C15—C16	1.370 (4)
C1—H1B	0.9300	C15—H15A	0.9300
N2—C25	1.364 (3)	C16—C17	1.362 (4)
N2—C26	1.368 (3)	C16—H16A	0.9300
N2—H2A	0.8600	C17—C18	1.394 (3)
O2—C9	1.219 (3)	C17—H17A	0.9300
C2—C3	1.394 (4)	C18—H18A	0.9300
C2—H2B	0.9300	C19—C26	1.382 (3)
O3—C27	1.331 (3)	C19—C20	1.442 (3)
O3—C28	1.453 (3)	C20—C25	1.410 (3)
C3—C4	1.372 (3)	C20—C21	1.415 (3)
C3—H3A	0.9300	C21—C22	1.363 (3)
O4—C27	1.207 (3)	C21—H21A	0.9300
C4—C5	1.402 (3)	C22—C23	1.397 (4)
C4—H4A	0.9300	C22—H22A	0.9300
C5—C6	1.413 (3)	C23—C24	1.371 (4)
C5—C7	1.440 (3)	C23—H23A	0.9300
C7—C8	1.375 (3)	C24—C25	1.397 (3)
C7—C12	1.520 (3)	C24—H24A	0.9300
C8—C9	1.460 (3)	C26—C27	1.467 (3)
C10—C11	1.379 (4)	C28—C29	1.486 (4)
C10—H10A	0.9700	C28—H28A	0.9700
C10—H10B	0.9700	C28—H28B	0.9700
C11—H11A	0.9600	C29—H29A	0.9600
C11—H11B	0.9600	C29—H29B	0.9600
C11—H11C	0.9600	C29—H29C	0.9600
C12—C19	1.522 (3)
C6—N1—C8	108.91 (19)	C18—C13—C12	122.3 (2)
C6—N1—H1A	125.5	C13—C14—C15	120.6 (3)
C8—N1—H1A	125.5	C13—C14—H14A	119.7
C9—O1—C10	117.3 (2)	C15—C14—H14A	119.7
C2—C1—C6	117.7 (3)	C16—C15—C14	120.8 (3)
C2—C1—H1B	121.2	C16—C15—H15A	119.6
C6—C1—H1B	121.2	C14—C15—H15A	119.6
C25—N2—C26	109.28 (19)	C17—C16—C15	119.7 (3)
C25—N2—H2A	125.4	C17—C16—H16A	120.2
C26—N2—H2A	125.4	C15—C16—H16A	120.2
C1—C2—C3	121.4 (3)	C16—C17—C18	120.0 (3)
C1—C2—H2B	119.3	C16—C17—H17A	120.0
C3—C2—H2B	119.3	C18—C17—H17A	120.0
C27—O3—C28	116.10 (19)	C13—C18—C17	120.6 (3)
C4—C3—C2	121.6 (3)	C13—C18—H18A	119.7
C4—C3—H3A	119.2	C17—C18—H18A	119.7
C2—C3—H3A	119.2	C26—C19—C20	105.12 (19)
C3—C4—C5	119.0 (2)	C26—C19—C12	125.5 (2)
C3—C4—H4A	120.5	C20—C19—C12	129.27 (19)
C5—C4—H4A	120.5	C25—C20—C21	117.3 (2)
C4—C5—C6	117.8 (2)	C25—C20—C19	107.5 (2)
C4—C5—C7	135.3 (2)	C21—C20—C19	135.2 (2)
C6—C5—C7	106.9 (2)	C22—C21—C20	119.4 (2)
N1—C6—C1	129.3 (2)	C22—C21—H21A	120.3
N1—C6—C5	108.1 (2)	C20—C21—H21A	120.3
C1—C6—C5	122.6 (2)	C21—C22—C23	121.8 (3)
C8—C7—C5	105.8 (2)	C21—C22—H22A	119.1
C8—C7—C12	126.1 (2)	C23—C22—H22A	119.1
C5—C7—C12	128.1 (2)	C24—C23—C22	121.3 (3)
N1—C8—C7	110.2 (2)	C24—C23—H23A	119.3
N1—C8—C9	116.0 (2)	C22—C23—H23A	119.3
C7—C8—C9	133.8 (2)	C23—C24—C25	116.9 (2)
O2—C9—O1	122.9 (3)	C23—C24—H24A	121.5
O2—C9—C8	122.9 (2)	C25—C24—H24A	121.5
O1—C9—C8	114.2 (2)	N2—C25—C24	129.0 (2)
C11—C10—O1	113.3 (3)	N2—C25—C20	107.6 (2)
C11—C10—H10A	108.9	C24—C25—C20	123.3 (2)
O1—C10—H10A	108.9	N2—C26—C19	110.4 (2)
C11—C10—H10B	108.9	N2—C26—C27	117.0 (2)
O1—C10—H10B	108.9	C19—C26—C27	132.5 (2)
H10A—C10—H10B	107.7	O4—C27—O3	122.8 (2)
C10—C11—H11A	109.5	O4—C27—C26	123.4 (2)
C10—C11—H11B	109.5	O3—C27—C26	113.7 (2)
H11A—C11—H11B	109.5	O3—C28—C29	107.3 (2)
C10—C11—H11C	109.5	O3—C28—H28A	110.2
H11A—C11—H11C	109.5	C29—C28—H28A	110.2
H11B—C11—H11C	109.5	O3—C28—H28B	110.2
C7—C12—C19	113.36 (18)	C29—C28—H28B	110.2
C7—C12—C13	112.51 (18)	H28A—C28—H28B	108.5
C19—C12—C13	112.78 (18)	C28—C29—H29A	109.5
C7—C12—H12A	105.8	C28—C29—H29B	109.5
C19—C12—H12A	105.8	H29A—C29—H29B	109.5
C13—C12—H12A	105.8	C28—C29—H29C	109.5
C14—C13—C18	118.2 (2)	H29A—C29—H29C	109.5
C14—C13—C12	119.4 (2)	H29B—C29—H29C	109.5
C6—C1—C2—C3	−1.2 (4)	C13—C14—C15—C16	0.5 (5)
C1—C2—C3—C4	0.5 (4)	C14—C15—C16—C17	1.3 (5)
C2—C3—C4—C5	0.4 (4)	C15—C16—C17—C18	−1.1 (4)
C3—C4—C5—C6	−0.6 (4)	C14—C13—C18—C17	2.8 (4)
C3—C4—C5—C7	−179.5 (3)	C12—C13—C18—C17	−175.3 (2)
C8—N1—C6—C1	179.6 (2)	C16—C17—C18—C13	−1.0 (4)
C8—N1—C6—C5	−0.8 (3)	C7—C12—C19—C26	152.1 (2)
C2—C1—C6—N1	−179.6 (2)	C13—C12—C19—C26	−78.6 (3)
C2—C1—C6—C5	0.9 (4)	C7—C12—C19—C20	−32.3 (3)
C4—C5—C6—N1	−179.6 (2)	C13—C12—C19—C20	97.0 (3)
C7—C5—C6—N1	−0.5 (3)	C26—C19—C20—C25	−0.8 (2)
C4—C5—C6—C1	0.0 (4)	C12—C19—C20—C25	−177.0 (2)
C7—C5—C6—C1	179.1 (2)	C26—C19—C20—C21	176.8 (3)
C4—C5—C7—C8	−179.5 (3)	C12—C19—C20—C21	0.5 (4)
C6—C5—C7—C8	1.6 (2)	C25—C20—C21—C22	−0.5 (4)
C4—C5—C7—C12	0.6 (4)	C19—C20—C21—C22	−177.8 (3)
C6—C5—C7—C12	−178.3 (2)	C20—C21—C22—C23	−0.2 (4)
C6—N1—C8—C7	1.9 (3)	C21—C22—C23—C24	0.7 (5)
C6—N1—C8—C9	−177.3 (2)	C22—C23—C24—C25	−0.5 (4)
C5—C7—C8—N1	−2.2 (3)	C26—N2—C25—C24	−178.0 (2)
C12—C7—C8—N1	177.8 (2)	C26—N2—C25—C20	0.3 (3)
C5—C7—C8—C9	176.9 (3)	C23—C24—C25—N2	177.9 (2)
C12—C7—C8—C9	−3.2 (4)	C23—C24—C25—C20	−0.2 (4)
C10—O1—C9—O2	2.7 (4)	C21—C20—C25—N2	−177.8 (2)
C10—O1—C9—C8	−176.1 (2)	C19—C20—C25—N2	0.3 (3)
N1—C8—C9—O2	−4.4 (4)	C21—C20—C25—C24	0.7 (4)
C7—C8—C9—O2	176.7 (3)	C19—C20—C25—C24	178.7 (2)
N1—C8—C9—O1	174.4 (2)	C25—N2—C26—C19	−0.8 (3)
C7—C8—C9—O1	−4.6 (4)	C25—N2—C26—C27	175.8 (2)
C9—O1—C10—C11	162.2 (4)	C20—C19—C26—N2	1.0 (3)
C8—C7—C12—C19	−76.6 (3)	C12—C19—C26—N2	177.4 (2)
C5—C7—C12—C19	103.4 (3)	C20—C19—C26—C27	−175.0 (2)
C8—C7—C12—C13	154.0 (2)	C12—C19—C26—C27	1.5 (4)
C5—C7—C12—C13	−26.1 (3)	C28—O3—C27—O4	0.4 (3)
C7—C12—C13—C14	−74.5 (3)	C28—O3—C27—C26	179.4 (2)
C19—C12—C13—C14	155.7 (2)	N2—C26—C27—O4	−3.8 (4)
C7—C12—C13—C18	103.5 (2)	C19—C26—C27—O4	171.9 (3)
C19—C12—C13—C18	−26.2 (3)	N2—C26—C27—O3	177.19 (19)
C18—C13—C14—C15	−2.5 (4)	C19—C26—C27—O3	−7.1 (4)
C12—C13—C14—C15	175.6 (2)	C27—O3—C28—C29	179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.21	2.955 (3)	144
N2—H2A···O4ii	0.86	2.07	2.880 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.21	2.955 (3)	144
N2—H2A⋯O4ii	0.86	2.07	2.880 (3)	157

Symmetry codes: (i) ; (ii) .