4,8-Dimeth-oxy-furo[2,3-b]quinoline (γ-fagarine).

The title mol-ecule, C(13)H(11)NO(3), a natural compound extracted from Phellodendron chinense, exhibits a near planar framework: the mean deviations from the furo[2,3-b]quinoline ring system and from the whole mol-ecule (not including the H atoms) are 0.006 and 0.062 Å, respectively.

Related literature

For the anti-HIV properties of furoquinolines, see: Wang et al. (2009 ▶); Cheng et al. (2005 ▶). For a related furoquinoline structure, see: Napolitano et al. (2003 ▶).

Experimental

Crystal data

C13H11NO3

M = 229.23

Orthorhombic,

a = 12.491 (5) Å

b = 12.155 (5) Å

c = 14.466 (5) Å

V = 2196.4 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.25 × 0.22 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.976, T max = 0.979

11659 measured reflections

2047 independent reflections

1278 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.129

S = 1.05

2047 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025062/bh2360sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025062/bh2360Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025062/bh2360Isup3.cml

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

C13H11NO3	F(000) = 960
Mr = 229.23	Dx = 1.386 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1884 reflections
a = 12.491 (5) Å	θ = 2.7–24.2°
b = 12.155 (5) Å	µ = 0.10 mm−1
c = 14.466 (5) Å	T = 296 K
V = 2196.4 (14) Å3	Block, colourless
Z = 8	0.25 × 0.22 × 0.21 mm

Bruker APEXII CCD diffractometer	2047 independent reflections
Radiation source: fine-focus sealed tube	1278 reflections with I > 2σ(I)
graphite	Rint = 0.068
φ and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −15→13
Tmin = 0.976, Tmax = 0.979	k = −13→14
11659 measured reflections	l = −16→17

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0376P)2 + 0.5982P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2047 reflections	Δρmax = 0.14 e Å−3
157 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0037 (8)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	1.0282 (3)	0.2044 (2)	−0.15171 (19)	0.0791 (8)
H1	1.0559	0.2307	−0.2072	0.095*
C2	1.0798 (2)	0.21016 (18)	−0.07253 (17)	0.0654 (7)
H2	1.1474	0.2401	−0.0627	0.078*
C3	1.01087 (17)	0.16075 (15)	−0.00386 (14)	0.0474 (5)
C4	1.00926 (16)	0.13961 (15)	0.08969 (14)	0.0476 (5)
C5	0.91729 (17)	0.08795 (16)	0.12813 (14)	0.0484 (5)
C6	0.9100 (2)	0.06319 (18)	0.22317 (16)	0.0651 (7)
H6	0.9662	0.0807	0.2627	0.078*
C7	0.8204 (2)	0.0136 (2)	0.2568 (2)	0.0819 (9)
H7	0.8159	−0.0021	0.3196	0.098*
C8	0.7351 (2)	−0.0142 (2)	0.1989 (2)	0.0835 (9)
H8	0.6746	−0.0480	0.2233	0.100*
C9	0.7403 (2)	0.00804 (18)	0.1070 (2)	0.0684 (7)
C10	0.83121 (17)	0.06121 (16)	0.06827 (16)	0.0524 (6)
C12	0.91869 (19)	0.12867 (17)	−0.05247 (15)	0.0544 (6)
C13	1.18328 (18)	0.2155 (2)	0.12003 (19)	0.0788 (8)
H13A	1.2177	0.1688	0.0755	0.118*
H13B	1.2303	0.2269	0.1716	0.118*
H13C	1.1667	0.2850	0.0920	0.118*
C14	0.5786 (3)	−0.0878 (3)	0.0754 (3)	0.1463 (17)
H14A	0.6090	−0.1531	0.1020	0.219*
H14B	0.5337	−0.1076	0.0242	0.219*
H14C	0.5367	−0.0501	0.1211	0.219*
N1	0.83129 (15)	0.08188 (15)	−0.02441 (14)	0.0603 (5)
O1	0.92925 (15)	0.15576 (15)	−0.14407 (11)	0.0756 (5)
O2	1.08678 (12)	0.16444 (13)	0.15127 (10)	0.0655 (5)
O3	0.66204 (14)	−0.01773 (15)	0.04411 (16)	0.0967 (7)

	U11	U22	U33	U12	U13	U23
C1	0.102 (2)	0.0731 (17)	0.0625 (18)	0.0109 (16)	0.0183 (17)	0.0169 (14)
C2	0.0779 (17)	0.0560 (14)	0.0623 (16)	0.0018 (12)	0.0185 (14)	0.0051 (12)
C3	0.0573 (13)	0.0387 (10)	0.0461 (12)	0.0039 (9)	0.0084 (10)	−0.0004 (9)
C4	0.0533 (13)	0.0420 (11)	0.0475 (13)	0.0008 (9)	0.0042 (11)	−0.0061 (9)
C5	0.0569 (13)	0.0397 (11)	0.0487 (13)	0.0001 (10)	0.0111 (11)	−0.0039 (9)
C6	0.0844 (18)	0.0595 (14)	0.0515 (15)	−0.0051 (13)	0.0160 (13)	−0.0006 (11)
C7	0.109 (2)	0.0672 (17)	0.0693 (18)	−0.0039 (16)	0.0394 (18)	0.0059 (14)
C8	0.076 (2)	0.0610 (16)	0.114 (3)	−0.0144 (14)	0.0458 (18)	−0.0081 (16)
C9	0.0574 (15)	0.0513 (13)	0.097 (2)	−0.0045 (12)	0.0184 (15)	−0.0099 (14)
C10	0.0535 (14)	0.0390 (11)	0.0647 (16)	0.0026 (10)	0.0100 (12)	−0.0055 (10)
C12	0.0681 (16)	0.0475 (12)	0.0476 (14)	0.0119 (11)	−0.0006 (12)	−0.0002 (10)
C13	0.0597 (15)	0.0896 (19)	0.0872 (19)	−0.0186 (14)	0.0017 (14)	−0.0050 (15)
C14	0.097 (2)	0.120 (3)	0.221 (5)	−0.061 (2)	0.023 (3)	−0.039 (3)
N1	0.0608 (13)	0.0559 (12)	0.0641 (14)	0.0049 (9)	−0.0062 (10)	−0.0050 (10)
O1	0.0975 (14)	0.0816 (12)	0.0476 (10)	0.0149 (10)	−0.0040 (10)	0.0084 (8)
O2	0.0644 (10)	0.0786 (11)	0.0535 (10)	−0.0168 (8)	0.0009 (8)	−0.0068 (8)
O3	0.0616 (11)	0.0872 (13)	0.1413 (19)	−0.0202 (10)	0.0027 (12)	−0.0185 (12)

C1—C2	1.316 (3)	C8—C9	1.358 (4)
C1—O1	1.375 (3)	C8—H8	0.9300
C1—H1	0.9300	C9—O3	1.372 (3)
C2—C3	1.446 (3)	C9—C10	1.422 (3)
C2—H2	0.9300	C10—N1	1.364 (3)
C3—C4	1.378 (3)	C12—N1	1.296 (3)
C3—C12	1.404 (3)	C12—O1	1.372 (3)
C4—O2	1.350 (2)	C13—O2	1.429 (3)
C4—C5	1.422 (3)	C13—H13A	0.9600
C5—C6	1.410 (3)	C13—H13B	0.9600
C5—C10	1.418 (3)	C13—H13C	0.9600
C6—C7	1.361 (3)	C14—O3	1.420 (3)
C6—H6	0.9300	C14—H14A	0.9600
C7—C8	1.397 (4)	C14—H14B	0.9600
C7—H7	0.9300	C14—H14C	0.9600
C2—C1—O1	113.2 (2)	C8—C9—C10	120.9 (3)
C2—C1—H1	123.4	O3—C9—C10	114.3 (2)
O1—C1—H1	123.4	N1—C10—C5	123.87 (19)
C1—C2—C3	106.5 (2)	N1—C10—C9	118.1 (2)
C1—C2—H2	126.7	C5—C10—C9	118.0 (2)
C3—C2—H2	126.7	N1—C12—O1	119.3 (2)
C4—C3—C12	115.35 (19)	N1—C12—C3	131.0 (2)
C4—C3—C2	139.6 (2)	O1—C12—C3	109.8 (2)
C12—C3—C2	105.1 (2)	O2—C13—H13A	109.5
O2—C4—C3	126.58 (19)	O2—C13—H13B	109.5
O2—C4—C5	114.85 (19)	H13A—C13—H13B	109.5
C3—C4—C5	118.56 (19)	O2—C13—H13C	109.5
C6—C5—C10	119.8 (2)	H13A—C13—H13C	109.5
C6—C5—C4	121.8 (2)	H13B—C13—H13C	109.5
C10—C5—C4	118.35 (19)	O3—C14—H14A	109.5
C7—C6—C5	119.7 (2)	O3—C14—H14B	109.5
C7—C6—H6	120.1	H14A—C14—H14B	109.5
C5—C6—H6	120.1	O3—C14—H14C	109.5
C6—C7—C8	121.3 (3)	H14A—C14—H14C	109.5
C6—C7—H7	119.3	H14B—C14—H14C	109.5
C8—C7—H7	119.3	C12—N1—C10	112.91 (19)
C9—C8—C7	120.2 (2)	C12—O1—C1	105.51 (19)
C9—C8—H8	119.9	C4—O2—C13	119.57 (18)
C7—C8—H8	119.9	C9—O3—C14	116.6 (3)
C8—C9—O3	124.8 (2)
O1—C1—C2—C3	0.2 (3)	C4—C5—C10—C9	179.04 (18)
C1—C2—C3—C4	−178.6 (2)	C8—C9—C10—N1	−179.6 (2)
C1—C2—C3—C12	−0.2 (2)	O3—C9—C10—N1	0.7 (3)
C12—C3—C4—O2	−178.62 (18)	C8—C9—C10—C5	1.4 (3)
C2—C3—C4—O2	−0.3 (4)	O3—C9—C10—C5	−178.24 (18)
C12—C3—C4—C5	0.4 (3)	C4—C3—C12—N1	−0.1 (3)
C2—C3—C4—C5	178.7 (2)	C2—C3—C12—N1	−179.0 (2)
O2—C4—C5—C6	−1.2 (3)	C4—C3—C12—O1	178.92 (17)
C3—C4—C5—C6	179.67 (19)	C2—C3—C12—O1	0.1 (2)
O2—C4—C5—C10	178.73 (17)	O1—C12—N1—C10	−179.06 (18)
C3—C4—C5—C10	−0.4 (3)	C3—C12—N1—C10	−0.1 (3)
C10—C5—C6—C7	0.1 (3)	C5—C10—N1—C12	0.1 (3)
C4—C5—C6—C7	−179.9 (2)	C9—C10—N1—C12	−178.82 (18)
C5—C6—C7—C8	0.4 (4)	N1—C12—O1—C1	179.27 (19)
C6—C7—C8—C9	0.0 (4)	C3—C12—O1—C1	0.1 (2)
C7—C8—C9—O3	178.7 (2)	C2—C1—O1—C12	−0.2 (3)
C7—C8—C9—C10	−1.0 (4)	C3—C4—O2—C13	−1.7 (3)
C6—C5—C10—N1	−179.89 (19)	C5—C4—O2—C13	179.32 (19)
C4—C5—C10—N1	0.2 (3)	C8—C9—O3—C14	−10.6 (4)
C6—C5—C10—C9	−1.0 (3)	C10—C9—O3—C14	169.1 (2)