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

The title compound, 4-(4-chloro­phenyl)-2,3,3a,4,5,9b-hexahydro­furo[3,2-c]quinoline, C₁₇H₁₆ClNO, was obtained as one of the diastereoisomers from the imino Diels–Alder reaction of an imine and dihydro­furan. The molecule is a cis (endo) cyclo­adduct isomer. The tetrahydrofuran ring adopts an envelope conformation, while the N-heterocyclic ring is in a sofa conformation. Intermolecular N—H...O hydrogen bonds lead to chains of molecules running along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.150
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15

   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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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: SHELXTL-PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

4-(4-chlorophenyl)-2,3,3a,4,5,9 b-hexahydrofuro[3,2-c]quinoline

Crystal data

C17H16ClNO	F(000) = 1200
Mr = 285.76	Dx = 1.333 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5262 reflections
a = 14.1068 (9) Å	θ = 2.4–27.9°
b = 9.5526 (6) Å	µ = 0.26 mm^−1
c = 21.1298 (13) Å	T = 273 K
V = 2847.4 (3) Å^3	Needle, colourless
Z = 8	0.18 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3010 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 28.0°, θmin = 1.9°
ω scans	h = −18→18
30760 measured reflections	k = −12→12
3412 independent reflections	l = −27→27

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0667P)^2 + 0.9682P] where P = (Fo^2 + 2Fc^2)/3
3412 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.24 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	0.73739 (5)	0.13204 (8)	0.44457 (3)	0.0814 (3)
O1	0.28980 (9)	0.10167 (16)	0.74049 (7)	0.0619 (4)
N1	0.57431 (10)	0.08259 (17)	0.74260 (7)	0.0457 (4)
C1	0.43501 (15)	0.0678 (2)	0.91723 (10)	0.0586 (5)
H1	0.4041	0.0661	0.9561	0.070*
C2	0.38578 (13)	0.0441 (2)	0.86199 (9)	0.0516 (4)
H2	0.3210	0.0266	0.8641	0.062*
C3	0.43004 (11)	0.04555 (17)	0.80327 (8)	0.0416 (4)
C4	0.37363 (11)	0.01643 (19)	0.74395 (9)	0.0475 (4)
H4	0.3556	−0.0826	0.7429	0.057*
C5	0.31865 (13)	0.2338 (2)	0.71568 (12)	0.0623 (5)
H5A	0.3316	0.2988	0.7499	0.075*
H5B	0.2689	0.2730	0.6893	0.075*
C6	0.40784 (13)	0.2095 (2)	0.67667 (10)	0.0566 (5)
H6A	0.4603	0.2647	0.6928	0.068*
H6B	0.3974	0.2337	0.6326	0.068*
C7	0.42753 (11)	0.05282 (19)	0.68395 (8)	0.0436 (4)
H7	0.3988	0.0028	0.6483	0.052*
C8	0.53218 (10)	0.01237 (17)	0.68851 (8)	0.0406 (4)
H8	0.5359	−0.0888	0.6958	0.049*
C9	0.52748 (10)	0.07396 (17)	0.80020 (8)	0.0396 (4)
C10	0.57695 (13)	0.0977 (2)	0.85662 (9)	0.0506 (4)
H10	0.6416	0.1163	0.8553	0.061*
C11	0.53125 (15)	0.0940 (2)	0.91392 (9)	0.0568 (5)
H11	0.5654	0.1092	0.9509	0.068*
C12	0.58525 (11)	0.04536 (17)	0.62813 (8)	0.0415 (4)
C13	0.58729 (16)	−0.0527 (2)	0.57999 (11)	0.0606 (5)
H13	0.5574	−0.1385	0.5859	0.073*
C14	0.63258 (17)	−0.0262 (2)	0.52357 (10)	0.0659 (6)
H14	0.6333	−0.0933	0.4917	0.079*
C15	0.67653 (13)	0.0999 (2)	0.51499 (9)	0.0535 (5)
C16	0.67550 (15)	0.1999 (2)	0.56133 (10)	0.0600 (5)
H16	0.7052	0.2857	0.5549	0.072*
C17	0.62967 (14)	0.1720 (2)	0.61793 (9)	0.0538 (5)
H17	0.6289	0.2396	0.6496	0.065*
H1N	0.6370 (18)	0.076 (2)	0.7445 (10)	0.058 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0698 (4)	0.1275 (6)	0.0469 (3)	0.0022 (3)	0.0102 (2)	0.0009 (3)
O1	0.0247 (5)	0.0870 (10)	0.0740 (9)	−0.0009 (6)	−0.0033 (6)	0.0072 (8)
N1	0.0254 (6)	0.0636 (9)	0.0480 (8)	−0.0038 (6)	−0.0029 (5)	−0.0008 (7)
C1	0.0628 (12)	0.0631 (12)	0.0499 (10)	0.0036 (10)	0.0098 (9)	0.0102 (9)
C2	0.0412 (9)	0.0531 (10)	0.0606 (11)	−0.0018 (8)	0.0073 (8)	0.0114 (8)
C3	0.0325 (7)	0.0395 (8)	0.0528 (9)	−0.0019 (6)	−0.0003 (6)	0.0068 (7)
C4	0.0286 (7)	0.0512 (10)	0.0627 (10)	−0.0091 (7)	−0.0034 (7)	0.0021 (8)
C5	0.0385 (9)	0.0689 (13)	0.0795 (14)	0.0091 (9)	−0.0062 (9)	−0.0033 (11)
C6	0.0413 (9)	0.0584 (11)	0.0702 (12)	0.0083 (8)	−0.0002 (8)	0.0135 (9)
C7	0.0299 (7)	0.0516 (9)	0.0495 (9)	−0.0055 (6)	−0.0075 (6)	−0.0022 (7)
C8	0.0331 (7)	0.0390 (8)	0.0498 (9)	−0.0006 (6)	−0.0032 (6)	−0.0003 (7)
C9	0.0312 (7)	0.0393 (8)	0.0483 (9)	0.0007 (6)	−0.0032 (6)	0.0039 (7)
C10	0.0393 (8)	0.0592 (11)	0.0533 (10)	−0.0010 (8)	−0.0082 (7)	0.0041 (8)
C11	0.0611 (11)	0.0611 (11)	0.0480 (10)	0.0029 (9)	−0.0096 (8)	0.0045 (8)
C12	0.0337 (7)	0.0423 (8)	0.0484 (9)	0.0054 (6)	−0.0030 (6)	−0.0022 (7)
C13	0.0674 (12)	0.0455 (10)	0.0689 (13)	−0.0013 (9)	0.0050 (10)	−0.0115 (9)
C14	0.0741 (14)	0.0672 (13)	0.0564 (12)	0.0077 (11)	0.0047 (10)	−0.0206 (10)
C15	0.0413 (9)	0.0751 (13)	0.0441 (9)	0.0100 (9)	0.0011 (7)	0.0004 (8)
C16	0.0617 (12)	0.0606 (12)	0.0577 (11)	−0.0101 (9)	0.0089 (9)	0.0004 (9)
C17	0.0580 (11)	0.0529 (10)	0.0505 (10)	−0.0098 (8)	0.0084 (8)	−0.0091 (8)

Geometric parameters (Å, º)

Cl1—C15	1.7450 (19)	C6—H6B	0.9700
O1—C5	1.426 (3)	C7—C8	1.529 (2)
O1—C4	1.438 (2)	C7—H7	0.9800
N1—C9	1.387 (2)	C8—C12	1.512 (2)
N1—C8	1.452 (2)	C8—H8	0.9800
N1—H1N	0.89 (3)	C9—C10	1.400 (2)
C1—C2	1.377 (3)	C10—C11	1.372 (3)
C1—C11	1.382 (3)	C10—H10	0.9300
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.389 (2)	C12—C17	1.379 (2)
C2—H2	0.9300	C12—C13	1.383 (3)
C3—C9	1.403 (2)	C13—C14	1.376 (3)
C3—C4	1.510 (2)	C13—H13	0.9300
C4—C7	1.519 (2)	C14—C15	1.367 (3)
C4—H4	0.9800	C14—H14	0.9300
C5—C6	1.522 (3)	C15—C16	1.368 (3)
C5—H5A	0.9700	C16—C17	1.386 (3)
C5—H5B	0.9700	C16—H16	0.9300
C6—C7	1.530 (3)	C17—H17	0.9300
C6—H6A	0.9700
C5—O1—C4	106.58 (13)	C8—C7—H7	108.9
C9—N1—C8	117.91 (13)	C6—C7—H7	108.9
C9—N1—H1N	115.5 (14)	N1—C8—C12	111.41 (13)
C8—N1—H1N	114.3 (14)	N1—C8—C7	109.15 (13)
C2—C1—C11	118.83 (18)	C12—C8—C7	111.85 (13)
C2—C1—H1	120.6	N1—C8—H8	108.1
C11—C1—H1	120.6	C12—C8—H8	108.1
C1—C2—C3	121.93 (17)	C7—C8—H8	108.1
C1—C2—H2	119.0	N1—C9—C10	120.01 (14)
C3—C2—H2	119.0	N1—C9—C3	121.25 (15)
C2—C3—C9	118.93 (16)	C10—C9—C3	118.72 (16)
C2—C3—C4	120.17 (15)	C11—C10—C9	120.86 (16)
C9—C3—C4	120.90 (15)	C11—C10—H10	119.6
O1—C4—C3	111.80 (15)	C9—C10—H10	119.6
O1—C4—C7	103.87 (14)	C10—C11—C1	120.72 (18)
C3—C4—C7	112.76 (13)	C10—C11—H11	119.6
O1—C4—H4	109.4	C1—C11—H11	119.6
C3—C4—H4	109.4	C17—C12—C13	118.00 (17)
C7—C4—H4	109.4	C17—C12—C8	122.65 (15)
O1—C5—C6	107.46 (16)	C13—C12—C8	119.32 (16)
O1—C5—H5A	110.2	C14—C13—C12	121.49 (19)
C6—C5—H5A	110.2	C14—C13—H13	119.3
O1—C5—H5B	110.2	C12—C13—H13	119.3
C6—C5—H5B	110.2	C15—C14—C13	119.18 (18)
H5A—C5—H5B	108.5	C15—C14—H14	120.4
C5—C6—C7	104.16 (16)	C13—C14—H14	120.4
C5—C6—H6A	110.9	C14—C15—C16	121.04 (18)
C7—C6—H6A	110.9	C14—C15—Cl1	119.42 (16)
C5—C6—H6B	110.9	C16—C15—Cl1	119.51 (17)
C7—C6—H6B	110.9	C15—C16—C17	119.21 (19)
H6A—C6—H6B	108.9	C15—C16—H16	120.4
C4—C7—C8	111.90 (14)	C17—C16—H16	120.4
C4—C7—C6	102.54 (14)	C12—C17—C16	121.07 (18)
C8—C7—C6	115.38 (14)	C12—C17—H17	119.5
C4—C7—H7	108.9	C16—C17—H17	119.5
C11—C1—C2—C3	0.1 (3)	C8—N1—C9—C3	−22.7 (2)
C1—C2—C3—C9	−0.9 (3)	C2—C3—C9—N1	−177.22 (16)
C1—C2—C3—C4	178.88 (18)	C4—C3—C9—N1	3.0 (2)
C5—O1—C4—C3	82.63 (18)	C2—C3—C9—C10	1.0 (2)
C5—O1—C4—C7	−39.23 (19)	C4—C3—C9—C10	−178.84 (16)
C2—C3—C4—O1	51.0 (2)	N1—C9—C10—C11	177.95 (17)
C9—C3—C4—O1	−129.20 (16)	C3—C9—C10—C11	−0.3 (3)
C2—C3—C4—C7	167.60 (16)	C9—C10—C11—C1	−0.6 (3)
C9—C3—C4—C7	−12.6 (2)	C2—C1—C11—C10	0.6 (3)
C4—O1—C5—C6	25.6 (2)	N1—C8—C12—C17	−32.0 (2)
O1—C5—C6—C7	−1.8 (2)	C7—C8—C12—C17	90.48 (19)
O1—C4—C7—C8	160.88 (14)	N1—C8—C12—C13	150.18 (17)
C3—C4—C7—C8	39.7 (2)	C7—C8—C12—C13	−87.35 (19)
O1—C4—C7—C6	36.64 (16)	C17—C12—C13—C14	0.4 (3)
C3—C4—C7—C6	−84.58 (17)	C8—C12—C13—C14	178.35 (18)
C5—C6—C7—C4	−20.90 (18)	C12—C13—C14—C15	0.0 (3)
C5—C6—C7—C8	−142.80 (17)	C13—C14—C15—C16	−0.4 (3)
C9—N1—C8—C12	173.43 (14)	C13—C14—C15—Cl1	177.92 (17)
C9—N1—C8—C7	49.4 (2)	C14—C15—C16—C17	0.5 (3)
C4—C7—C8—N1	−57.68 (18)	Cl1—C15—C16—C17	−177.90 (16)
C6—C7—C8—N1	59.05 (19)	C13—C12—C17—C16	−0.4 (3)
C4—C7—C8—C12	178.58 (14)	C8—C12—C17—C16	−178.25 (18)
C6—C7—C8—C12	−64.70 (19)	C15—C16—C17—C12	0.0 (3)
C8—N1—C9—C10	159.12 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.89 (3)	2.19 (3)	3.066 (2)	168 (2)
C6—H6A···N1	0.97	2.60	2.988 (2)	105

Symmetry code: (i) x+1/2, y, −z+3/2.