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

The title compound, C₁₇H₁₆N₂O₃, is one of the diastereoisomers formed as the result of the Diels–Alder reaction of 1-(4-nitrophenyl)methylidene]-N-phenylamine and dihydro­furan catalyzed by zirconium tetra­chloride. The furan ring adopts an envelope conformation, while the N-heterocyclic ring prefers a sofa conformation. Mol­ecules are linked into centrosymmetric dimers by N—H...O hydrogen-bond inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.056
• wR factor = 0.163
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

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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.

4-(4-nitrophenyl)-2,3,3a,4,5,9 b-hexahydro furo[3,2-c]quinoline

Crystal data

C17H16N2O3	Z = 2
Mr = 296.32	F(000) = 312
Triclinic, P1	Dx = 1.353 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.109 (1) Å	Cell parameters from 2986 reflections
b = 9.2626 (10) Å	θ = 2.4–27.8°
c = 9.7553 (11) Å	µ = 0.09 mm^−1
α = 103.411 (2)°	T = 273 K
β = 102.791 (2)°	Block, yellow
γ = 107.081 (2)°	0.20 × 0.15 × 0.10 mm
V = 727.28 (14) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2549 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 28.0°, θmin = 2.3°
ω scans	h = −11→12
8354 measured reflections	k = −12→12
3308 independent reflections	l = −12→12

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) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0819P)^2 + 0.1431P] where P = (Fo^2 + 2Fc^2)/3
3308 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.16 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
O1	0.79382 (18)	0.13712 (16)	1.02054 (14)	0.0749 (4)
O2	−0.04776 (18)	0.2998 (2)	0.43917 (18)	0.0861 (5)
O3	−0.0843 (2)	0.3557 (2)	0.6527 (2)	0.0902 (5)
N1	0.4235 (2)	−0.10150 (18)	0.69462 (19)	0.0649 (4)
H1N	0.325 (3)	−0.156 (3)	0.669 (2)	0.076 (6)*
N2	−0.01463 (18)	0.30655 (18)	0.56938 (19)	0.0636 (4)
C1	0.7428 (3)	−0.3391 (3)	0.7726 (2)	0.0715 (5)
H1	0.8144	−0.3920	0.7871	0.086*
C2	0.7970 (2)	−0.1759 (2)	0.82518 (19)	0.0610 (4)
H2	0.9062	−0.1187	0.8756	0.073*
C3	0.6920 (2)	−0.0941 (2)	0.80481 (17)	0.0526 (4)
C4	0.7526 (2)	0.0834 (2)	0.8606 (2)	0.0589 (4)
H4	0.8500	0.1255	0.8332	0.071*
C5	0.8002 (3)	0.2959 (3)	1.0618 (3)	0.0904 (7)
H5A	0.9110	0.3690	1.0903	0.108*
H5B	0.7603	0.3165	1.1458	0.108*
C6	0.6990 (3)	0.3204 (2)	0.9338 (3)	0.0807 (6)
H6A	0.7632	0.4050	0.9050	0.097*
H6B	0.6109	0.3477	0.9582	0.097*
C7	0.6340 (2)	0.1611 (2)	0.80886 (19)	0.0570 (4)
H7	0.6399	0.1787	0.7146	0.068*
C8	0.4617 (2)	0.0576 (2)	0.79315 (18)	0.0535 (4)
H8	0.4572	0.0505	0.8909	0.064*
C9	0.5283 (2)	−0.1806 (2)	0.72604 (18)	0.0558 (4)
C10	0.4746 (3)	−0.3465 (2)	0.6739 (2)	0.0718 (5)
H10	0.3659	−0.4051	0.6225	0.086*
C11	0.5801 (3)	−0.4241 (2)	0.6976 (2)	0.0771 (6)
H11	0.5422	−0.5349	0.6630	0.093*
C12	0.3386 (2)	0.12581 (19)	0.73454 (17)	0.0514 (4)
C13	0.2921 (2)	0.1153 (2)	0.58588 (18)	0.0600 (4)
H13	0.3383	0.0667	0.5220	0.072*
C14	0.1780 (2)	0.1761 (2)	0.53161 (19)	0.0599 (4)
H14	0.1466	0.1682	0.4319	0.072*
C15	0.11203 (19)	0.24836 (18)	0.62823 (18)	0.0522 (4)
C16	0.1573 (2)	0.2634 (2)	0.77661 (19)	0.0600 (4)
H16	0.1125	0.3143	0.8404	0.072*
C17	0.2705 (2)	0.2015 (2)	0.82872 (18)	0.0612 (5)
H17	0.3018	0.2105	0.9287	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0825 (9)	0.0668 (8)	0.0586 (8)	0.0280 (7)	−0.0043 (6)	0.0133 (6)
O2	0.0744 (9)	0.1094 (12)	0.0817 (10)	0.0417 (9)	0.0100 (8)	0.0467 (9)
O3	0.0803 (10)	0.1017 (12)	0.1064 (12)	0.0541 (9)	0.0332 (9)	0.0339 (9)
N1	0.0497 (8)	0.0537 (8)	0.0797 (11)	0.0156 (7)	0.0051 (7)	0.0186 (7)
N2	0.0511 (8)	0.0581 (9)	0.0782 (11)	0.0184 (7)	0.0128 (8)	0.0246 (8)
C1	0.0933 (15)	0.0805 (13)	0.0634 (11)	0.0532 (12)	0.0289 (10)	0.0316 (10)
C2	0.0641 (10)	0.0786 (12)	0.0523 (9)	0.0352 (9)	0.0209 (8)	0.0277 (8)
C3	0.0549 (9)	0.0611 (10)	0.0464 (8)	0.0236 (7)	0.0172 (7)	0.0208 (7)
C4	0.0485 (9)	0.0629 (10)	0.0634 (10)	0.0171 (8)	0.0147 (8)	0.0233 (8)
C5	0.1038 (17)	0.0725 (14)	0.0744 (14)	0.0343 (12)	−0.0014 (12)	0.0113 (11)
C6	0.0789 (13)	0.0539 (10)	0.0866 (14)	0.0168 (9)	−0.0020 (11)	0.0177 (10)
C7	0.0581 (10)	0.0554 (9)	0.0550 (9)	0.0151 (7)	0.0133 (7)	0.0241 (8)
C8	0.0569 (9)	0.0579 (9)	0.0511 (9)	0.0230 (7)	0.0160 (7)	0.0248 (7)
C9	0.0591 (10)	0.0550 (9)	0.0530 (9)	0.0219 (8)	0.0142 (7)	0.0187 (7)
C10	0.0742 (12)	0.0569 (10)	0.0722 (12)	0.0206 (9)	0.0091 (10)	0.0157 (9)
C11	0.1024 (17)	0.0590 (11)	0.0726 (13)	0.0377 (11)	0.0220 (12)	0.0201 (9)
C12	0.0527 (9)	0.0550 (9)	0.0493 (9)	0.0189 (7)	0.0160 (7)	0.0221 (7)
C13	0.0703 (11)	0.0717 (11)	0.0478 (9)	0.0353 (9)	0.0221 (8)	0.0213 (8)
C14	0.0682 (11)	0.0719 (11)	0.0444 (8)	0.0302 (9)	0.0151 (8)	0.0231 (8)
C15	0.0475 (8)	0.0489 (8)	0.0573 (9)	0.0148 (7)	0.0121 (7)	0.0193 (7)
C16	0.0617 (10)	0.0679 (11)	0.0555 (10)	0.0282 (8)	0.0236 (8)	0.0180 (8)
C17	0.0684 (11)	0.0791 (12)	0.0445 (9)	0.0318 (9)	0.0209 (8)	0.0253 (8)

Geometric parameters (Å, º)

O1—C5	1.412 (3)	C6—H6A	0.9700
O1—C4	1.447 (2)	C6—H6B	0.9700
O2—N2	1.221 (2)	C7—C8	1.532 (2)
O3—N2	1.224 (2)	C7—H7	0.9800
N1—C9	1.389 (2)	C8—C12	1.511 (2)
N1—C8	1.453 (2)	C8—H8	0.9800
N1—H1N	0.84 (2)	C9—C10	1.394 (2)
N2—C15	1.472 (2)	C10—C11	1.371 (3)
C1—C2	1.371 (3)	C10—H10	0.9300
C1—C11	1.385 (3)	C11—H11	0.9300
C1—H1	0.9300	C12—C17	1.389 (2)
C2—C3	1.393 (2)	C12—C13	1.389 (2)
C2—H2	0.9300	C13—C14	1.385 (2)
C3—C9	1.400 (2)	C13—H13	0.9300
C3—C4	1.491 (2)	C14—C15	1.375 (2)
C4—C7	1.524 (2)	C14—H14	0.9300
C4—H4	0.9800	C15—C16	1.376 (2)
C5—C6	1.484 (3)	C16—C17	1.379 (2)
C5—H5A	0.9700	C16—H16	0.9300
C5—H5B	0.9700	C17—H17	0.9300
C6—C7	1.532 (3)
C5—O1—C4	106.44 (15)	C4—C7—H7	110.5
C9—N1—C8	118.39 (14)	C6—C7—H7	110.5
C9—N1—H1N	115.8 (15)	C8—C7—H7	110.5
C8—N1—H1N	111.9 (15)	N1—C8—C12	109.96 (13)
O2—N2—O3	123.25 (17)	N1—C8—C7	108.79 (14)
O2—N2—C15	118.52 (16)	C12—C8—C7	112.23 (13)
O3—N2—C15	118.21 (16)	N1—C8—H8	108.6
C2—C1—C11	119.19 (18)	C12—C8—H8	108.6
C2—C1—H1	120.4	C7—C8—H8	108.6
C11—C1—H1	120.4	N1—C9—C10	120.81 (16)
C1—C2—C3	121.43 (18)	N1—C9—C3	120.22 (15)
C1—C2—H2	119.3	C10—C9—C3	118.90 (17)
C3—C2—H2	119.3	C11—C10—C9	120.79 (19)
C2—C3—C9	119.10 (16)	C11—C10—H10	119.6
C2—C3—C4	120.96 (16)	C9—C10—H10	119.6
C9—C3—C4	119.90 (15)	C10—C11—C1	120.57 (19)
O1—C4—C3	109.45 (14)	C10—C11—H11	119.7
O1—C4—C7	104.28 (14)	C1—C11—H11	119.7
C3—C4—C7	116.38 (14)	C17—C12—C13	118.65 (15)
O1—C4—H4	108.8	C17—C12—C8	120.56 (14)
C3—C4—H4	108.8	C13—C12—C8	120.79 (15)
C7—C4—H4	108.8	C14—C13—C12	120.87 (16)
O1—C5—C6	108.76 (18)	C14—C13—H13	119.6
O1—C5—H5A	109.9	C12—C13—H13	119.6
C6—C5—H5A	109.9	C15—C14—C13	118.62 (15)
O1—C5—H5B	109.9	C15—C14—H14	120.7
C6—C5—H5B	109.9	C13—C14—H14	120.7
H5A—C5—H5B	108.3	C14—C15—C16	122.07 (16)
C5—C6—C7	105.25 (17)	C14—C15—N2	118.65 (15)
C5—C6—H6A	110.7	C16—C15—N2	119.26 (16)
C7—C6—H6A	110.7	C15—C16—C17	118.58 (16)
C5—C6—H6B	110.7	C15—C16—H16	120.7
C7—C6—H6B	110.7	C17—C16—H16	120.7
H6A—C6—H6B	108.8	C16—C17—C12	121.19 (15)
C4—C7—C6	101.77 (14)	C16—C17—H17	119.4
C4—C7—C8	110.36 (13)	C12—C17—H17	119.4
C6—C7—C8	112.98 (17)
C11—C1—C2—C3	0.0 (3)	C4—C3—C9—N1	2.5 (3)
C1—C2—C3—C9	−1.4 (3)	C2—C3—C9—C10	1.8 (3)
C1—C2—C3—C4	−179.12 (16)	C4—C3—C9—C10	179.50 (16)
C5—O1—C4—C3	−161.85 (17)	N1—C9—C10—C11	176.17 (19)
C5—O1—C4—C7	−36.7 (2)	C3—C9—C10—C11	−0.8 (3)
C2—C3—C4—O1	−72.65 (19)	C9—C10—C11—C1	−0.7 (3)
C9—C3—C4—O1	109.66 (17)	C2—C1—C11—C10	1.0 (3)
C2—C3—C4—C7	169.49 (15)	N1—C8—C12—C17	134.16 (17)
C9—C3—C4—C7	−8.2 (2)	C7—C8—C12—C17	−104.61 (18)
C4—O1—C5—C6	23.9 (3)	N1—C8—C12—C13	−46.3 (2)
O1—C5—C6—C7	−1.5 (3)	C7—C8—C12—C13	74.9 (2)
O1—C4—C7—C6	34.17 (18)	C17—C12—C13—C14	−1.2 (3)
C3—C4—C7—C6	154.83 (16)	C8—C12—C13—C14	179.25 (16)
O1—C4—C7—C8	−86.02 (16)	C12—C13—C14—C15	0.4 (3)
C3—C4—C7—C8	34.6 (2)	C13—C14—C15—C16	0.7 (3)
C5—C6—C7—C4	−19.9 (2)	C13—C14—C15—N2	−177.27 (15)
C5—C6—C7—C8	98.5 (2)	O2—N2—C15—C14	−5.6 (2)
C9—N1—C8—C12	176.64 (15)	O3—N2—C15—C14	172.60 (17)
C9—N1—C8—C7	53.4 (2)	O2—N2—C15—C16	176.31 (16)
C4—C7—C8—N1	−55.20 (18)	O3—N2—C15—C16	−5.5 (2)
C6—C7—C8—N1	−168.39 (14)	C14—C15—C16—C17	−1.1 (3)
C4—C7—C8—C12	−177.11 (14)	N2—C15—C16—C17	176.92 (15)
C6—C7—C8—C12	69.70 (19)	C15—C16—C17—C12	0.2 (3)
C8—N1—C9—C10	156.30 (17)	C13—C12—C17—C16	0.9 (3)
C8—N1—C9—C3	−26.8 (2)	C8—C12—C17—C16	−179.59 (16)
C2—C3—C9—N1	−175.18 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.84 (2)	2.34 (2)	3.164 (2)	171 (2)

Symmetry code: (i) −x, −y, −z+1.