A diastereoisomer of furo[3,2-c]quinoline

The title compound, 7-chloro-8-fluoro-4-phenyl-2,3,3a,4,5,9b-hexahydro­furo[3,2-c]quinoline, C₁₇H₁₅ClFNO, was obtained from the imine Diels-Alder reaction of an N-benzyl­ideneaniline and 2,3-dihydro­furan catalyzed by ZrCl₄. An isomer that crystallizes in the centrosymmetric monoclinic space group C2/c is presented. The furan ring is in a twist conformation, while the pyridine ring is in a sofa conformation. An intermolecular hydrogen bond between the pyridine NH group and the O atom of the furan ring in a neighboring molecule forms chains along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.066
• wR factor = 0.154
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997; molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

7-chloro-8-fluoro-4-phenyl-2,3,3a,4,5,9 b-hexahydrofuro[3,2-c]quinoline

Crystal data

C17H15ClFNO	F(000) = 1264
Mr = 303.75	Dx = 1.36 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5098 reflections
a = 25.826 (2) Å	θ = 2.4–21.2°
b = 6.8065 (6) Å	µ = 0.27 mm^−1
c = 17.2924 (16) Å	T = 273 K
β = 102.490 (2)°	Needle, colorless
V = 2967.8 (4) Å^3	0.20 × 0.15 × 0.10 mm
Z = 8

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2074 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 25°, θmin = 1.6°
ω scans	h = −28→30
7178 measured reflections	k = −8→7
2607 independent reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0698P)^2 + 1.7065P] where P = (Fo^2 + 2Fc^2)/3
2607 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.10033 (3)	1.16166 (14)	0.11297 (5)	0.0598 (3)
F1	1.09269 (8)	0.7454 (3)	0.06877 (14)	0.0773 (7)
O1	0.92619 (9)	0.4753 (3)	0.14844 (14)	0.0592 (6)
C1	1.04737 (12)	0.8173 (5)	0.08544 (17)	0.0465 (8)
C2	1.00440 (12)	0.6981 (4)	0.08050 (17)	0.0452 (8)
H2	1.0068	0.5665	0.0673	0.054*
C3	0.95731 (11)	0.7700 (4)	0.09486 (16)	0.0370 (7)
C4	0.91125 (12)	0.6314 (4)	0.09259 (18)	0.0433 (7)
H4	0.9001	0.5763	0.0392	0.052*
C5	0.92008 (15)	0.5521 (5)	0.2226 (2)	0.0652 (10)
H5A	0.952	0.6209	0.2487	0.078*
H5B	0.9134	0.4466	0.2569	0.078*
C6	0.87390 (16)	0.6907 (5)	0.2056 (2)	0.0624 (10)
H6A	0.8824	0.8121	0.2351	0.075*
H6B	0.843	0.6319	0.2198	0.075*
C7	0.86375 (12)	0.7288 (4)	0.11668 (19)	0.0452 (8)
H7	0.8314	0.6594	0.0908	0.054*
C8	0.85844 (11)	0.9461 (4)	0.09243 (17)	0.0416 (7)
H8	0.8544	0.9529	0.0348	0.05*
C9	0.95417 (11)	0.9682 (4)	0.11496 (16)	0.0380 (7)
C10	0.99884 (12)	1.0862 (4)	0.12160 (17)	0.0422 (7)
H10	0.9974	1.2171	0.1364	0.051*
C11	1.04508 (11)	1.0120 (5)	0.10660 (16)	0.0416 (7)
C12	0.81072 (12)	1.0436 (4)	0.11298 (18)	0.0438 (7)
C13	0.76210 (14)	1.0271 (6)	0.0618 (2)	0.0700 (11)
H13	0.7592	0.9564	0.0151	0.084*
C14	0.71789 (15)	1.1131 (7)	0.0786 (3)	0.0875 (14)
H14	0.6854	1.0992	0.0432	0.105*
C15	0.72060 (15)	1.2190 (6)	0.1465 (3)	0.0766 (12)
H15	0.6905	1.2783	0.1573	0.092*
C16	0.76855 (16)	1.2361 (6)	0.1984 (3)	0.0737 (11)
H16	0.7711	1.3068	0.2451	0.088*
C17	0.81330 (13)	1.1489 (5)	0.1818 (2)	0.0601 (9)
H17	0.8456	1.1616	0.2177	0.072*
N1	0.90741 (9)	1.0447 (3)	0.12859 (16)	0.0465 (7)
H1	0.9074	1.1474	0.1576	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0391 (5)	0.0809 (7)	0.0615 (5)	−0.0120 (4)	0.0154 (4)	−0.0080 (5)
F1	0.0442 (12)	0.0899 (16)	0.1043 (16)	0.0166 (11)	0.0303 (11)	−0.0222 (13)
O1	0.0702 (16)	0.0276 (11)	0.0843 (17)	0.0056 (11)	0.0269 (13)	0.0054 (11)
C1	0.0362 (17)	0.058 (2)	0.0466 (17)	0.0152 (16)	0.0123 (13)	−0.0055 (15)
C2	0.050 (2)	0.0384 (17)	0.0495 (18)	0.0122 (15)	0.0164 (14)	−0.0092 (14)
C3	0.0425 (17)	0.0327 (15)	0.0364 (15)	0.0045 (13)	0.0101 (12)	−0.0004 (12)
C4	0.0482 (18)	0.0337 (16)	0.0490 (17)	−0.0009 (14)	0.0127 (14)	−0.0085 (13)
C5	0.075 (3)	0.058 (2)	0.066 (2)	−0.003 (2)	0.0217 (19)	0.0156 (19)
C6	0.083 (3)	0.0421 (19)	0.072 (2)	0.0027 (18)	0.039 (2)	0.0046 (17)
C7	0.0413 (18)	0.0359 (16)	0.0601 (19)	−0.0065 (13)	0.0144 (14)	−0.0104 (14)
C8	0.0370 (17)	0.0418 (17)	0.0474 (16)	0.0027 (13)	0.0126 (13)	−0.0031 (14)
C9	0.0378 (17)	0.0314 (15)	0.0463 (16)	0.0064 (13)	0.0121 (13)	0.0029 (12)
C10	0.0444 (18)	0.0319 (15)	0.0518 (18)	0.0013 (14)	0.0139 (14)	−0.0009 (13)
C11	0.0333 (16)	0.0551 (19)	0.0360 (15)	0.0017 (14)	0.0068 (12)	0.0016 (13)
C12	0.0391 (18)	0.0383 (17)	0.0574 (18)	0.0063 (14)	0.0179 (14)	0.0055 (14)
C13	0.039 (2)	0.090 (3)	0.077 (2)	0.0123 (19)	0.0043 (18)	−0.014 (2)
C14	0.040 (2)	0.118 (4)	0.100 (3)	0.018 (2)	0.005 (2)	−0.010 (3)
C15	0.044 (2)	0.083 (3)	0.111 (3)	0.017 (2)	0.034 (2)	0.004 (3)
C16	0.066 (3)	0.078 (3)	0.087 (3)	0.008 (2)	0.037 (2)	−0.020 (2)
C17	0.0398 (19)	0.071 (2)	0.072 (2)	0.0021 (17)	0.0158 (16)	−0.0138 (19)
N1	0.0399 (15)	0.0278 (13)	0.0766 (18)	0.0021 (11)	0.0233 (13)	−0.0091 (12)

Geometric parameters (Å, º)

Cl1—C11	1.737 (3)	C8—C12	1.508 (4)
F1—C1	1.356 (3)	C8—H8	0.98
O1—C5	1.425 (4)	N1—C8	1.449 (4)
O1—C4	1.431 (4)	N1—C9	1.381 (3)
C1—C2	1.362 (4)	C9—C10	1.390 (4)
C1—C11	1.380 (4)	C10—C11	1.372 (4)
C2—C3	1.382 (4)	C10—H10	0.93
C2—H2	0.93	C12—C13	1.375 (4)
C3—C9	1.400 (4)	C12—C17	1.379 (4)
C3—C4	1.512 (4)	C13—C14	1.369 (5)
C4—C7	1.529 (4)	C13—H13	0.93
C4—H4	0.98	C14—C15	1.367 (6)
C5—C6	1.499 (5)	C14—H14	0.93
C5—H5A	0.97	C15—C16	1.368 (6)
C5—H5B	0.97	C15—H15	0.93
C6—C7	1.526 (4)	C16—C17	1.383 (5)
C6—H6A	0.97	C16—H16	0.93
C6—H6B	0.97	C17—H17	0.93
C7—C8	1.535 (4)	N1—H1	0.86
C7—H7	0.98
C5—O1—C4	105.6 (2)	N1—C8—C7	108.1 (2)
F1—C1—C2	120.1 (3)	C12—C8—C7	112.9 (2)
F1—C1—C11	119.4 (3)	N1—C8—H8	107.9
C2—C1—C11	120.5 (3)	C12—C8—H8	107.9
C1—C2—C3	121.0 (3)	C7—C8—H8	107.9
C1—C2—H2	119.5	N1—C9—C10	120.6 (3)
C3—C2—H2	119.5	N1—C9—C3	120.4 (3)
C2—C3—C9	119.1 (3)	C10—C9—C3	119.1 (3)
C2—C3—C4	119.5 (3)	C11—C10—C9	120.8 (3)
C9—C3—C4	121.3 (3)	C11—C10—H10	119.6
O1—C4—C3	110.5 (2)	C9—C10—H10	119.6
O1—C4—C7	104.7 (2)	C10—C11—C1	119.5 (3)
C3—C4—C7	113.3 (2)	C10—C11—Cl1	120.6 (2)
O1—C4—H4	109.4	C1—C11—Cl1	119.9 (2)
C3—C4—H4	109.4	C13—C12—C17	117.7 (3)
C7—C4—H4	109.4	C13—C12—C8	119.4 (3)
O1—C5—C6	107.0 (3)	C17—C12—C8	122.9 (3)
O1—C5—H5A	110.3	C14—C13—C12	121.1 (4)
C6—C5—H5A	110.3	C14—C13—H13	119.5
O1—C5—H5B	110.3	C12—C13—H13	119.5
C6—C5—H5B	110.3	C15—C14—C13	121.2 (4)
H5A—C5—H5B	108.6	C15—C14—H14	119.4
C5—C6—C7	105.1 (3)	C13—C14—H14	119.4
C5—C6—H6A	110.7	C14—C15—C16	118.6 (4)
C7—C6—H6A	110.7	C14—C15—H15	120.7
C5—C6—H6B	110.7	C16—C15—H15	120.7
C7—C6—H6B	110.7	C15—C16—C17	120.4 (4)
H6A—C6—H6B	108.8	C15—C16—H16	119.8
C6—C7—C4	103.2 (3)	C17—C16—H16	119.8
C6—C7—C8	115.1 (2)	C12—C17—C16	121.0 (3)
C4—C7—C8	111.9 (2)	C12—C17—H17	119.5
C6—C7—H7	108.8	C16—C17—H17	119.5
C4—C7—H7	108.8	C9—N1—C8	117.7 (2)
C8—C7—H7	108.8	C9—N1—H1	121.1
N1—C8—C12	112.1 (2)	C8—N1—H1	121.1
F1—C1—C2—C3	−178.0 (3)	C4—C3—C9—C10	175.5 (3)
C11—C1—C2—C3	1.4 (5)	N1—C9—C10—C11	−178.7 (3)
C1—C2—C3—C9	−0.2 (4)	C3—C9—C10—C11	1.8 (4)
C1—C2—C3—C4	−177.1 (3)	C9—C10—C11—C1	−0.6 (4)
C5—O1—C4—C3	83.2 (3)	C9—C10—C11—Cl1	178.6 (2)
C5—O1—C4—C7	−39.0 (3)	F1—C1—C11—C10	178.4 (3)
C2—C3—C4—O1	57.9 (3)	C2—C1—C11—C10	−1.0 (4)
C9—C3—C4—O1	−119.0 (3)	F1—C1—C11—Cl1	−0.9 (4)
C2—C3—C4—C7	175.0 (3)	C2—C1—C11—Cl1	179.8 (2)
C9—C3—C4—C7	−1.9 (4)	N1—C8—C12—C13	153.3 (3)
C4—O1—C5—C6	33.9 (3)	C7—C8—C12—C13	−84.4 (4)
O1—C5—C6—C7	−14.7 (4)	N1—C8—C12—C17	−27.2 (4)
C5—C6—C7—C4	−8.5 (3)	C7—C8—C12—C17	95.1 (4)
C5—C6—C7—C8	−130.6 (3)	C17—C12—C13—C14	0.3 (6)
O1—C4—C7—C6	28.7 (3)	C8—C12—C13—C14	179.8 (4)
C3—C4—C7—C6	−91.7 (3)	C12—C13—C14—C15	0.3 (7)
O1—C4—C7—C8	153.0 (2)	C13—C14—C15—C16	−0.7 (7)
C3—C4—C7—C8	32.6 (3)	C14—C15—C16—C17	0.5 (7)
C6—C7—C8—N1	59.9 (3)	C13—C12—C17—C16	−0.5 (5)
C4—C7—C8—N1	−57.5 (3)	C8—C12—C17—C16	180.0 (3)
C6—C7—C8—C12	−64.7 (3)	C15—C16—C17—C12	0.1 (6)
C4—C7—C8—C12	178.0 (2)	C10—C9—N1—C8	156.4 (3)
C2—C3—C9—N1	179.1 (3)	C3—C9—N1—C8	−24.2 (4)
C4—C3—C9—N1	−4.0 (4)	C12—C8—N1—C9	179.3 (2)
C2—C3—C9—C10	−1.4 (4)	C7—C8—N1—C9	54.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	2.30	2.979 (3)	136
C10—H10···O1^i	0.93	2.58	3.336 (4)	138
C6—H6A···N1	0.97	2.61	2.971 (4)	102

Symmetry code: (i) x, y+1, z.