Methyl 1-(7-acetamido-5,8-dimeth-oxy-quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl-ate.

The title compound, C(27)H(24)N(4)O(5), is an inter-mediate in the synthesis of lavendamycin via a ruthenium-catalysed [2 + 2 + 2] cyclo-addition. An intra-molecular hydrogen-bond bridge from the carboline to the quinoline stabilizes a highly planar geometry [maximum deviation = 0.065 (6) Å] for the two rigid units. This hydrogen-bond-stabilized coplanarity has a very close analogy in the structure of the anti-tumor anti-biotic streptonigrin in the solid state and in solution. Inter-molecular hydrogen-bond bridges of amides groups along the a axis and π-π stacking inter-actions [centroid-centroid distance = 3.665 (9) Å] connect mol-ecules arranged in a parallel manner.

Related literature

For metal-catalysed transformations of tethered alkynyl-ynamides to carbolines and other heteroannulated indoles, see: Nissen et al. (2011 ▶); Dassonneville et al. (2010 ▶, 2011 ▶). For the synthesis of the natural product lavendamycin (systematic name 1-(7-amino-5,8-dioxoquinolin-2-yl)-4-methyl-9H-pyrido[3,4-b]indole-3-carb­oxy­lic acid) via [2 + 2 + 2] cyclo­addition, see: Nissen & Detert (2011 ▶). For the isololation of lavendamycin from streptomyces lavendulae, see: Doyle et al. (1981 ▶). For the anti-tumor activity of lavendamycin, see: Fang et al. (2003 ▶). For the preparation of lavandamycin, see: Behforouz et al. (1996 ▶) Godard et al. (1993 ▶). For related structures, see: Chiu & Lipscomb (1975 ▶); Harding et al. (1993 ▶).

Experimental

Crystal data

C27H24N4O5

M = 484.50

Triclinic,

a = 4.646 (10) Å

b = 13.81 (3) Å

c = 18.768 (19) Å

α = 102.06 (9)°

β = 95.23 (10)°

γ = 96.85 (11)°

V = 1161 (4) Å3

Z = 2

Cu Kα radiation

μ = 0.80 mm−1

T = 193 K

0.58 × 0.06 × 0.03 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4993 measured reflections

4412 independent reflections

2069 reflections with I > 2σ(I)

R int = 0.054

3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.248

S = 0.99

4412 reflections

330 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018794/bt5551sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018794/bt5551Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018794/bt5551Isup3.cml

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

C27H24N4O5	Z = 2
Mr = 484.50	F(000) = 508
Triclinic, P1	Dx = 1.386 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 4.646 (10) Å	Cell parameters from 25 reflections
b = 13.81 (3) Å	θ = 10–25°
c = 18.768 (19) Å	µ = 0.80 mm−1
α = 102.06 (9)°	T = 193 K
β = 95.23 (10)°	10, yellow
γ = 96.85 (11)°	0.58 × 0.06 × 0.03 mm
V = 1161 (4) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.054
Radiation source: rotating anode	θmax = 70.0°, θmin = 2.4°
graphite	h = −5→0
ω/2θ scans	k = −16→16
4993 measured reflections	l = −22→22
4412 independent reflections	3 standard reflections every 60 min
2069 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.083	H-atom parameters constrained
wR(F2) = 0.248	w = 1/[σ2(Fo2) + (0.1159P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
4412 reflections	Δρmax = 0.26 e Å−3
330 parameters	Δρmin = −0.34 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: 0.0010 (5)

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
O1	0.9484 (9)	0.6415 (3)	0.3958 (2)	0.0631 (12)
O2	1.1937 (9)	0.5349 (3)	0.43953 (19)	0.0530 (11)
O3	0.5569 (7)	−0.0529 (2)	0.16500 (18)	0.0381 (8)
N4	0.7247 (8)	−0.2335 (3)	0.1735 (2)	0.0314 (9)
H4	0.5329	−0.2404	0.1660	0.038*
O5	1.1210 (8)	−0.3053 (3)	0.1464 (2)	0.0691 (14)
O6	1.4309 (8)	−0.0606 (3)	0.38367 (19)	0.0469 (10)
N1	0.9463 (9)	0.3816 (3)	0.3424 (2)	0.0363 (10)
N2	0.4724 (9)	0.2191 (3)	0.1858 (2)	0.0367 (10)
H2	0.4994	0.1561	0.1806	0.044*
N3	0.8225 (9)	0.1206 (3)	0.2585 (2)	0.0349 (10)
C1	0.9992 (12)	0.5579 (4)	0.3929 (3)	0.0392 (12)
C2	1.3460 (13)	0.6178 (4)	0.4953 (3)	0.0506 (15)
H2A	1.4680	0.6626	0.4725	0.076*
H2B	1.4695	0.5926	0.5305	0.076*
H2C	1.2039	0.6545	0.5210	0.076*
C3	0.8488 (11)	0.4675 (3)	0.3360 (3)	0.0362 (12)
C4	0.8328 (11)	0.2958 (3)	0.2955 (3)	0.0361 (12)
C5	0.6143 (11)	0.2973 (3)	0.2397 (3)	0.0341 (11)
C6	0.2800 (11)	0.2556 (4)	0.1412 (3)	0.0352 (11)
C7	0.2906 (11)	0.3594 (4)	0.1682 (3)	0.0355 (11)
C8	0.5118 (11)	0.3860 (3)	0.2323 (3)	0.0344 (11)
C9	0.6334 (11)	0.4754 (3)	0.2817 (3)	0.0368 (12)
C10	0.5268 (13)	0.5721 (4)	0.2747 (3)	0.0508 (15)
H10A	0.4642	0.6039	0.3214	0.076*
H10B	0.3616	0.5585	0.2359	0.076*
H10C	0.6850	0.6169	0.2623	0.076*
C11	0.1095 (11)	0.4101 (4)	0.1309 (3)	0.0416 (13)
H11	0.1105	0.4800	0.1476	0.050*
C12	−0.0723 (12)	0.3573 (4)	0.0691 (3)	0.0490 (14)
H12	−0.1993	0.3914	0.0439	0.059*
C13	−0.0731 (12)	0.2558 (4)	0.0431 (3)	0.0477 (14)
H13	−0.1969	0.2220	−0.0002	0.057*
C14	0.0991 (12)	0.2038 (4)	0.0782 (3)	0.0432 (13)
H14	0.0965	0.1340	0.0605	0.052*
C15	0.9462 (11)	0.2043 (3)	0.3056 (3)	0.0367 (12)
C16	0.9155 (11)	0.0334 (3)	0.2670 (3)	0.0320 (11)
C17	0.7812 (10)	−0.0564 (3)	0.2176 (3)	0.0330 (11)
C18	0.6517 (15)	−0.0421 (5)	0.0971 (3)	0.0645 (19)
H18A	0.7902	0.0195	0.1047	0.097*
H18B	0.4831	−0.0388	0.0627	0.097*
H18C	0.7473	−0.0996	0.0769	0.097*
C19	0.8703 (10)	−0.1450 (3)	0.2232 (3)	0.0323 (11)
C20	0.8550 (10)	−0.3067 (4)	0.1373 (3)	0.0374 (12)
C21	0.6628 (11)	−0.3906 (4)	0.0857 (3)	0.0447 (14)
H21A	0.7272	−0.3984	0.0368	0.067*
H21B	0.4610	−0.3762	0.0833	0.067*
H21C	0.6731	−0.4525	0.1029	0.067*
C22	1.0881 (11)	−0.1513 (4)	0.2785 (3)	0.0373 (12)
H22	1.1437	−0.2143	0.2820	0.045*
C23	1.2197 (10)	−0.0657 (4)	0.3273 (3)	0.0338 (11)
C24	1.5056 (13)	−0.1523 (4)	0.3972 (3)	0.0514 (15)
H24A	1.3311	−0.1930	0.4064	0.077*
H24B	1.6528	−0.1387	0.4403	0.077*
H24C	1.5846	−0.1885	0.3544	0.077*
C25	1.1358 (11)	0.0293 (3)	0.3224 (3)	0.0345 (11)
C26	1.2625 (12)	0.1205 (4)	0.3705 (3)	0.0413 (13)
H26	1.4150	0.1214	0.4080	0.050*
C27	1.1656 (11)	0.2061 (4)	0.3626 (3)	0.0392 (12)
H27	1.2453	0.2676	0.3955	0.047*

	U11	U22	U33	U12	U13	U23
O1	0.068 (3)	0.032 (2)	0.077 (3)	0.006 (2)	−0.016 (2)	−0.004 (2)
O2	0.073 (3)	0.037 (2)	0.042 (2)	−0.003 (2)	−0.006 (2)	0.0036 (17)
O3	0.038 (2)	0.0337 (18)	0.0398 (19)	0.0018 (16)	−0.0003 (17)	0.0052 (15)
N4	0.022 (2)	0.0242 (19)	0.044 (2)	0.0010 (16)	0.0027 (18)	0.0013 (17)
O5	0.0185 (19)	0.067 (3)	0.097 (3)	0.0068 (18)	−0.001 (2)	−0.033 (2)
O6	0.047 (2)	0.039 (2)	0.050 (2)	0.0009 (17)	−0.0097 (18)	0.0100 (17)
N1	0.039 (2)	0.028 (2)	0.040 (2)	−0.0042 (18)	0.009 (2)	0.0057 (18)
N2	0.036 (2)	0.031 (2)	0.038 (2)	−0.0019 (18)	0.002 (2)	0.0024 (18)
N3	0.038 (2)	0.027 (2)	0.034 (2)	−0.0025 (18)	0.0078 (19)	−0.0016 (17)
C1	0.042 (3)	0.029 (3)	0.044 (3)	−0.002 (2)	0.012 (3)	0.003 (2)
C2	0.069 (4)	0.033 (3)	0.041 (3)	−0.006 (3)	0.000 (3)	0.000 (2)
C3	0.047 (3)	0.024 (2)	0.038 (3)	0.001 (2)	0.016 (2)	0.007 (2)
C4	0.040 (3)	0.032 (3)	0.033 (3)	−0.004 (2)	0.013 (2)	0.001 (2)
C5	0.033 (3)	0.027 (2)	0.039 (3)	−0.002 (2)	0.010 (2)	0.003 (2)
C6	0.031 (3)	0.037 (3)	0.037 (3)	0.004 (2)	0.008 (2)	0.005 (2)
C7	0.030 (3)	0.039 (3)	0.035 (3)	0.001 (2)	0.011 (2)	0.002 (2)
C8	0.034 (3)	0.036 (3)	0.034 (3)	0.001 (2)	0.015 (2)	0.008 (2)
C9	0.042 (3)	0.028 (2)	0.038 (3)	0.000 (2)	0.012 (2)	0.002 (2)
C10	0.058 (4)	0.038 (3)	0.050 (3)	0.004 (3)	−0.007 (3)	0.004 (3)
C11	0.041 (3)	0.035 (3)	0.052 (3)	0.010 (2)	0.010 (3)	0.011 (3)
C12	0.041 (3)	0.052 (3)	0.053 (3)	0.004 (3)	0.004 (3)	0.012 (3)
C13	0.039 (3)	0.050 (3)	0.048 (3)	−0.002 (3)	−0.002 (3)	0.004 (3)
C14	0.045 (3)	0.035 (3)	0.047 (3)	0.001 (2)	0.007 (3)	0.005 (2)
C15	0.040 (3)	0.031 (3)	0.036 (3)	−0.002 (2)	0.006 (2)	0.002 (2)
C16	0.033 (3)	0.028 (2)	0.034 (3)	0.001 (2)	0.005 (2)	0.006 (2)
C17	0.029 (3)	0.033 (3)	0.034 (3)	0.002 (2)	0.000 (2)	0.005 (2)
C18	0.075 (5)	0.071 (4)	0.040 (3)	−0.016 (4)	−0.004 (3)	0.016 (3)
C19	0.028 (3)	0.025 (2)	0.039 (3)	−0.003 (2)	0.001 (2)	0.002 (2)
C20	0.020 (2)	0.040 (3)	0.046 (3)	0.004 (2)	−0.003 (2)	−0.001 (2)
C21	0.032 (3)	0.039 (3)	0.054 (3)	0.002 (2)	0.002 (3)	−0.009 (3)
C22	0.038 (3)	0.032 (3)	0.041 (3)	0.003 (2)	0.005 (2)	0.008 (2)
C23	0.026 (2)	0.038 (3)	0.037 (3)	0.001 (2)	0.003 (2)	0.011 (2)
C24	0.047 (3)	0.049 (3)	0.057 (4)	0.003 (3)	−0.008 (3)	0.020 (3)
C25	0.032 (3)	0.034 (3)	0.033 (3)	−0.006 (2)	0.002 (2)	0.003 (2)
C26	0.040 (3)	0.038 (3)	0.038 (3)	−0.007 (2)	−0.004 (2)	0.004 (2)
C27	0.043 (3)	0.031 (3)	0.037 (3)	−0.003 (2)	0.002 (2)	0.001 (2)

O1—C1	1.198 (6)	C16—C17	1.420 (7)
O2—C1	1.313 (6)	C17—C19	1.359 (7)
O2—C2	1.442 (6)	C19—C22	1.406 (7)
O3—C17	1.380 (6)	C20—C21	1.485 (7)
O3—C18	1.417 (7)	C22—C23	1.373 (7)
N4—C20	1.336 (6)	C23—C25	1.431 (7)
N4—C19	1.425 (6)	C25—C26	1.414 (7)
O5—C20	1.229 (6)	C26—C27	1.346 (7)
O6—C23	1.360 (6)	N2—H2	0.8800
O6—C24	1.419 (6)	N4—H4	0.8800
N1—C4	1.337 (6)	C2—H2A	0.9800
N1—C3	1.342 (6)	C2—H2B	0.9800
N2—C5	1.370 (6)	C2—H2C	0.9800
N2—C6	1.380 (6)	C10—H10A	0.9800
N3—C15	1.330 (6)	C10—H10B	0.9800
N3—C16	1.362 (6)	C10—H10C	0.9800
C1—C3	1.512 (7)	C11—H11	0.9500
C3—C9	1.392 (7)	C12—H12	0.9500
C4—C5	1.396 (7)	C13—H13	0.9500
C4—C15	1.467 (7)	C14—H14	0.9500
C5—C8	1.395 (7)	C18—H18A	0.9800
C6—C14	1.392 (7)	C18—H18B	0.9800
C6—C7	1.410 (7)	C18—H18C	0.9800
C7—C11	1.388 (7)	C21—H21A	0.9800
C7—C8	1.462 (7)	C21—H21B	0.9800
C8—C9	1.400 (7)	C21—H21C	0.9800
C9—C10	1.505 (7)	C22—H22	0.9500
C11—C12	1.383 (7)	C24—H24A	0.9800
C12—C13	1.383 (8)	C24—H24B	0.9800
C13—C14	1.352 (7)	C24—H24C	0.9800
C15—C27	1.402 (7)	C26—H26	0.9500
C16—C25	1.406 (7)	C27—H27	0.9500
C1—O2—C2	115.5 (4)	C16—C25—C26	117.4 (5)
C17—O3—C18	113.6 (4)	C16—C25—C23	119.0 (4)
C20—N4—C19	125.5 (4)	C26—C25—C23	123.6 (5)
C23—O6—C24	117.3 (4)	C27—C26—C25	119.5 (5)
C4—N1—C3	120.2 (5)	C26—C27—C15	119.7 (5)
C5—N2—C6	108.6 (4)	C6—N2—H2	126.00
C15—N3—C16	117.6 (4)	C5—N2—H2	126.00
O1—C1—O2	123.1 (5)	C19—N4—H4	117.00
O1—C1—C3	124.4 (5)	C20—N4—H4	117.00
O2—C1—C3	112.5 (4)	O2—C2—H2A	110.00
N1—C3—C9	124.4 (4)	O2—C2—H2B	109.00
N1—C3—C1	113.9 (5)	O2—C2—H2C	109.00
C9—C3—C1	121.7 (4)	H2A—C2—H2B	109.00
N1—C4—C5	118.9 (5)	H2A—C2—H2C	109.00
N1—C4—C15	117.8 (5)	H2B—C2—H2C	109.00
C5—C4—C15	123.2 (4)	C9—C10—H10A	109.00
N2—C5—C8	110.2 (4)	C9—C10—H10B	109.00
N2—C5—C4	128.5 (5)	C9—C10—H10C	110.00
C8—C5—C4	121.4 (4)	H10A—C10—H10B	109.00
N2—C6—C14	128.4 (5)	H10A—C10—H10C	109.00
N2—C6—C7	109.4 (4)	H10B—C10—H10C	109.00
C14—C6—C7	122.2 (5)	C7—C11—H11	120.00
C11—C7—C6	118.2 (5)	C12—C11—H11	121.00
C11—C7—C8	136.1 (5)	C11—C12—H12	119.00
C6—C7—C8	105.7 (4)	C13—C12—H12	119.00
C5—C8—C9	119.0 (5)	C12—C13—H13	119.00
C5—C8—C7	106.1 (4)	C14—C13—H13	119.00
C9—C8—C7	134.8 (5)	C6—C14—H14	121.00
C3—C9—C8	116.0 (5)	C13—C14—H14	121.00
C3—C9—C10	124.0 (4)	O3—C18—H18A	110.00
C8—C9—C10	120.0 (5)	O3—C18—H18B	109.00
C12—C11—C7	119.0 (5)	O3—C18—H18C	109.00
C11—C12—C13	121.4 (5)	H18A—C18—H18B	109.00
C14—C13—C12	121.3 (5)	H18A—C18—H18C	109.00
C13—C14—C6	118.0 (5)	H18B—C18—H18C	109.00
N3—C15—C27	123.1 (5)	C20—C21—H21A	109.00
N3—C15—C4	115.5 (5)	C20—C21—H21B	109.00
C27—C15—C4	121.4 (4)	C20—C21—H21C	110.00
N3—C16—C25	122.7 (4)	H21A—C21—H21B	109.00
N3—C16—C17	117.9 (4)	H21A—C21—H21C	109.00
C25—C16—C17	119.4 (4)	H21B—C21—H21C	109.00
C19—C17—O3	120.5 (4)	C19—C22—H22	120.00
C19—C17—C16	120.0 (4)	C23—C22—H22	120.00
O3—C17—C16	119.5 (4)	O6—C24—H24A	109.00
C17—C19—C22	121.7 (4)	O6—C24—H24B	109.00
C17—C19—N4	118.0 (4)	O6—C24—H24C	109.00
C22—C19—N4	120.2 (4)	H24A—C24—H24B	109.00
O5—C20—N4	121.8 (5)	H24A—C24—H24C	109.00
O5—C20—C21	121.4 (5)	H24B—C24—H24C	110.00
N4—C20—C21	116.8 (4)	C25—C26—H26	120.00
C23—C22—C19	119.5 (5)	C27—C26—H26	120.00
O6—C23—C22	125.9 (5)	C15—C27—H27	120.00
O6—C23—C25	113.7 (4)	C26—C27—H27	120.00
C22—C23—C25	120.5 (5)
C2—O2—C1—O1	−0.2 (8)	N2—C6—C14—C13	179.9 (5)
C2—O2—C1—C3	179.9 (4)	C7—C6—C14—C13	−0.7 (8)
C4—N1—C3—C9	−1.0 (7)	C16—N3—C15—C27	0.1 (7)
C4—N1—C3—C1	−179.9 (4)	C16—N3—C15—C4	−178.3 (4)
O1—C1—C3—N1	178.5 (5)	N1—C4—C15—N3	178.7 (4)
O2—C1—C3—N1	−1.6 (6)	C5—C4—C15—N3	−1.4 (7)
O1—C1—C3—C9	−0.4 (8)	N1—C4—C15—C27	0.3 (7)
O2—C1—C3—C9	179.5 (5)	C5—C4—C15—C27	−179.8 (5)
C3—N1—C4—C5	0.6 (7)	C15—N3—C16—C25	−0.6 (7)
C3—N1—C4—C15	−179.5 (4)	C15—N3—C16—C17	179.1 (5)
C6—N2—C5—C8	1.5 (5)	C18—O3—C17—C19	−88.9 (6)
C6—N2—C5—C4	−178.0 (5)	C18—O3—C17—C16	92.3 (6)
N1—C4—C5—N2	179.1 (5)	N3—C16—C17—C19	179.0 (4)
C15—C4—C5—N2	−0.8 (8)	C25—C16—C17—C19	−1.4 (7)
N1—C4—C5—C8	−0.4 (7)	N3—C16—C17—O3	−2.3 (7)
C15—C4—C5—C8	179.7 (4)	C25—C16—C17—O3	177.4 (4)
C5—N2—C6—C14	177.4 (5)	O3—C17—C19—C22	−176.8 (4)
C5—N2—C6—C7	−2.0 (5)	C16—C17—C19—C22	2.0 (7)
N2—C6—C7—C11	−179.4 (4)	O3—C17—C19—N4	−0.2 (7)
C14—C6—C7—C11	1.1 (7)	C16—C17—C19—N4	178.6 (4)
N2—C6—C7—C8	1.7 (5)	C20—N4—C19—C17	135.4 (5)
C14—C6—C7—C8	−177.8 (5)	C20—N4—C19—C22	−47.9 (7)
N2—C5—C8—C9	−178.9 (4)	C19—N4—C20—O5	2.7 (8)
C4—C5—C8—C9	0.6 (7)	C19—N4—C20—C21	−177.5 (4)
N2—C5—C8—C7	−0.4 (5)	C17—C19—C22—C23	−1.4 (7)
C4—C5—C8—C7	179.1 (4)	N4—C19—C22—C23	−178.0 (5)
C11—C7—C8—C5	−179.3 (6)	C24—O6—C23—C22	−5.6 (7)
C6—C7—C8—C5	−0.8 (5)	C24—O6—C23—C25	173.7 (4)
C11—C7—C8—C9	−1.1 (10)	C19—C22—C23—O6	179.5 (5)
C6—C7—C8—C9	177.4 (5)	C19—C22—C23—C25	0.2 (7)
N1—C3—C9—C8	1.2 (7)	N3—C16—C25—C26	−0.1 (7)
C1—C3—C9—C8	179.9 (5)	C17—C16—C25—C26	−179.8 (5)
N1—C3—C9—C10	−179.7 (5)	N3—C16—C25—C23	179.9 (4)
C1—C3—C9—C10	−0.9 (8)	C17—C16—C25—C23	0.2 (7)
C5—C8—C9—C3	−1.0 (7)	O6—C23—C25—C16	−179.0 (4)
C7—C8—C9—C3	−179.0 (5)	C22—C23—C25—C16	0.3 (7)
C5—C8—C9—C10	179.9 (5)	O6—C23—C25—C26	1.0 (7)
C7—C8—C9—C10	1.9 (8)	C22—C23—C25—C26	−179.7 (5)
C6—C7—C11—C12	−0.1 (7)	C16—C25—C26—C27	1.4 (7)
C8—C7—C11—C12	178.3 (5)	C23—C25—C26—C27	−178.7 (5)
C7—C11—C12—C13	−1.2 (8)	C25—C26—C27—C15	−1.8 (8)
C11—C12—C13—C14	1.6 (9)	N3—C15—C27—C26	1.1 (8)
C12—C13—C14—C6	−0.6 (8)	C4—C15—C27—C26	179.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3	0.88	2.17	2.693 (7)	118
N4—H4···O5i	0.88	1.98	2.824 (8)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3	0.88	2.17	2.693 (7)	118
N4—H4⋯O5i	0.88	1.98	2.824 (8)	160

Symmetry code: (i) .