Methyl 1-(7-acetamido-5,8-dimeth­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate

Nissen, F.; Schollmeyer, D.; Detert, H.

doi:10.1107/S1600536811018794

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1497-o1498

doi:10.1107/S1600536811018794

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Methyl 1-(7-acetamido-5,8-dimethoxyquinolin-2-yl)-4-methyl-β-carboline-3-carboxylate

Felix Nissen,^a Dieter Schollmeyer ^a and Heiner Detert ^a ^*

^aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: detert@uni-mainz.de

(Received 16 May 2011; accepted 17 May 2011; online 25 May 2011)

The title compound, C₂₇H₂₄N₄O₅, is an intermediate in the synthesis of lavendamycin via a ruthenium-catalysed [2 + 2 + 2] cycloaddition. An intramolecular 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 antitumor antibiotic streptonigrin in the solid state and in solution. Intermolecular hydrogen-bond bridges of amides groups along the a axis and π–π stacking interactions [centroid–centroid distance = 3.665 (9) Å] connect molecules 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_r = 484.50
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.083
wR(F²) = 0.248
S = 0.99
4412 reflections
330 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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) x-1, y, z.

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.

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536811018794/bt5551Isup3.cml

checkCIF report

Comment top

The title compound was prepared as part of a larger project focusing on the synthesis of indolo-annulated heterocycles via [2 + 2+2] cycloaddition of alkynyl-ynamides and nitriles or heterocumulenes catalyzed by rhodium or ruthenium (Nissen et al., 2011; Dassonneville et al., 2011) and is a synthetic precursor of the natural product lavendamycin (Nissen & Detert, 2011). The molecule is built up by two rigid and planar units, both are coplanar. This flat structure is stabilized by an intramolecular hydrogen bond from the carboline-NH to the quinoline-N N2—H2···N3 with a distance of 2.17 Å. Whereas the ester group is coplanar with the carboline core [torsion angle O1—C1—C3—C9 of -0.4 (8)°], the acetamido group is twisted out of the plane of the quinoline framework. The torsion angle C20—N4—C19—C22 amounts to -47.9 (7)°. This torsion can result from the sterical hindrance due to the neighbouring methoxy group, but its ability to act as a hydrogen bridge donor and acceptor is important for the formation of crystals of the title compound. Parallel molecules, arranged in the shape of tilted staples are connected to infinite chains via H-bridging along the a-axis. The tilt angle of the mean plane of the molecules relative to the ab-plane is 54.3°. The second interaction is π-π-stacking, resulting in a distance of only 3.665 (9) Å of the centroids of the pyrrole ring (N2—C6) and the benzo-ring (C6—C14) (symmetry code 1+X,Y,Z). Two molecules, connected via a center of inversion fill the unit cell.

Related literature top

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 top

Pd/C (10%, 47 mg, 44 µmol, 5 mol%) was added to a suspension of Methyl 1-(5,8-dimethoxy-7-nitroquinolin-2-yl)-4-methyl-β-carboline-3-carboxylate (405 mg, 0.86 mmol) (Nissen & Detert, 2011) in THF (170 ml) and the mixture was stirred 13 h under H₂ atmosphere. Ac₂O (5.0 ml) was added and the mixture was heated to 323 K. After 3 h the solvent was removed in vacuo, the residue dissolved in CH₂Cl₂ and filtered through celite. The filtrate was washed with aqueous NaHCO₃ (8%, 8 ml), dried (MgSO₄) and concentrated. Crystallization from chloroform/diethyl ether yielded the title compound (399 mg, 0.82 mmol, 96%) as a bright yellow solid. M.p. 467–468 K R_f: 0.12 (SiO₂, hexane:ethyl acetate:ethanol 6:3:1).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Spek, 2009).

Figures top

	Fig. 1. View of compound I. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the packing diagram showing the hydrogen bonds. View along b-axis.

Methyl 1-(7-acetamido-5,8-dimethoxyquinolin-2-yl)-4-methyl-β-carboline-3- carboxylate top

Crystal data top

C₂₇H₂₄N₄O₅	Z = 2
M_r = 484.50	F(000) = 508
Triclinic, P1	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.054
Radiation source: rotating anode	θ_max = 70.0°, θ_min = 2.4°
Graphite monochromator	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 top

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(F_o²) + (0.1159P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
4412 reflections	Δρ_max = 0.26 e Å⁻³
330 parameters	Δρ_min = −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)

Crystal data top

C₂₇H₂₄N₄O₅	γ = 96.85 (11)°
M_r = 484.50	V = 1161 (4) Å³
Triclinic, P1	Z = 2
a = 4.646 (10) Å	Cu Kα radiation
b = 13.81 (3) Å	µ = 0.80 mm⁻¹
c = 18.768 (19) Å	T = 193 K
α = 102.06 (9)°	0.58 × 0.06 × 0.03 mm
β = 95.23 (10)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.054
4993 measured reflections	3 standard reflections every 60 min
4412 independent reflections	intensity decay: 2%
2069 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.083	0 restraints
wR(F²) = 0.248	H-atom parameters constrained
S = 0.99	Δρ_max = 0.26 e Å⁻³
4412 reflections	Δρ_min = −0.34 e Å⁻³
330 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₄N₄O₅
M_r	484.50
Crystal system, space group	Triclinic, P1
Temperature (K)	193
a, b, c (Å)	4.646 (10), 13.81 (3), 18.768 (19)
α, β, γ (°)	102.06 (9), 95.23 (10), 96.85 (11)
V (Å³)	1161 (4)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.58 × 0.06 × 0.03

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4993, 4412, 2069
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.248, 0.99
No. of reflections	4412
No. of parameters	330
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.34

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Behforouz, M., Haddad, J., Cai, W., Arnold, M. B., Mohammadi, F., Sousa, A. C. & Horn, M. A. (1996). J. Org. Chem. 61, 6552–6555. CrossRef PubMed CAS Google Scholar
Chiu, Y.-Y. H. & Lipscomb, W. N. (1975). J. Am. Chem. Soc. 97, 2525–2530. CrossRef PubMed CAS Web of Science Google Scholar
Dassonneville, B., Schollmeyer, D., Witulski, B. & Detert, H. (2010). Acta Cryst. E66, o2665. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761–762. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Fang, A. Y., Linardic, C. M., Richardson, D. A. & Behforouz, M. A. (2003). Mol. Cancer Ther. 2, 517–526. Web of Science PubMed CAS Google Scholar
Godard, A., Rocca, P., Fourquez, J. M., Rovera, J. Z., Marsais, F. & Quéguiner, G. (1993). Tetrahedron Lett. 34, 7919–7922. CrossRef CAS Google Scholar
Harding, M. M., Long, G. V. & Brown, C. L. (1993). J. Med. Chem. 36, 3056–3060. CrossRef CAS PubMed Web of Science Google Scholar
Nissen, F. & Detert, H. (2011). Eur. J. Org. Chem. pp. 2845–2853. Web of Science CSD CrossRef Google Scholar
Nissen, F., Richard, V., Alayrac, C. & Witulski, B. (2011). Chem. Commun. doi: 10.1039/C1CC11298H. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1497-o1498

doi:10.1107/S1600536811018794

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl 1-(7-acetamido-5,8-dimeth­­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

Methyl 1-(7-acetamido-5,8-dimethoxyquinolin-2-yl)-4-methyl-β-carboline-3-carboxylate