N-(4-Methyl­phenyl)-N-(5-nitro­furfuryl)-N-prop-2-ynyl­amine

The title compound, C₁₅H₁₄N₂O₃, is the first example of a structurally determined tertiary amine with both N-5-nitro­furfuryl and N-prop-2-ynyl moieties. The mol­ecule is not planar, i.e. the furan ring is inclined at an angle of 84.35 (4)° to the phenyl ring. The crystal structure is dominated by van der Waals forces. The terminal alkynyl group as the strongest C-H hydrogen-bond donor is not involved in hydrogen-bond formation.

Computing details

Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

N-(4-Methylphenyl)-N-2-propynyl-N-5-nitro-2-furfurylamine

Crystal data

C15H14N2O3	Z = 2
Mr = 270.28	F(000) = 284
Triclinic, P1	Dx = 1.314 Mg m^−3
a = 8.8490 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2060 (13) Å	Cell parameters from 57 reflections
c = 9.8438 (19) Å	θ = 8–17.8°
α = 63.196 (14)°	µ = 0.09 mm^−1
β = 76.908 (15)°	T = 293 K
γ = 73.937 (13)°	Prism, pale orange
V = 683.0 (2) Å^3	0.69 × 0.45 × 0.14 mm

Data collection

Philips PW1100 updated by Stoe diffractometer	Rint = 0.105
Radiation source: fine-focus sealed tube	θmax = 29.0°, θmin = 3.0°
Graphite monochromator	h = −12→12
ω scans	k = −12→12
7040 measured reflections	l = −13→13
3520 independent reflections	5 standard reflections every 90 min
1997 reflections with I > 2σ(I)	intensity decay: 7.2%

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)] = 0.039	Hydrogen site location: geom and dmap
wR(F^2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Calculated w = 1/[σ^2(Fo^2) + (0.0189P)^2] where P = (Fo^2 + 2Fc^2)/3
3520 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.47394 (9)	0.77179 (11)	0.74520 (9)	0.0474 (2)
O2	0.67701 (14)	0.47179 (16)	0.61158 (15)	0.0784 (3)
O3	0.69057 (13)	0.49415 (15)	0.81856 (14)	0.0769 (3)
N1	0.11488 (11)	1.07782 (13)	0.75658 (10)	0.0438 (2)
N2	0.63536 (13)	0.54186 (15)	0.69909 (14)	0.0569 (3)
C1	0.28225 (14)	1.01103 (18)	0.76444 (15)	0.0515 (3)
H1A	0.3005	0.9498	0.8712	0.062*
H1B	0.3380	1.1023	0.7195	0.062*
C2	0.34977 (13)	0.89850 (16)	0.68373 (13)	0.0455 (3)
C3	0.31406 (15)	0.88957 (18)	0.56119 (15)	0.0536 (3)
H3	0.2343	0.9607	0.5006	0.064*
C4	0.42096 (16)	0.75164 (18)	0.54272 (15)	0.0532 (3)
H4	0.4259	0.7136	0.4685	0.064*
C5	0.51347 (14)	0.68762 (17)	0.65516 (14)	0.0473 (3)
C6	0.00588 (13)	0.97352 (14)	0.83140 (11)	0.0402 (2)
C7	0.05328 (16)	0.80830 (16)	0.93425 (12)	0.0477 (3)
H7	0.1597	0.7655	0.9482	0.057*
C8	−0.05664 (19)	0.70851 (18)	1.01507 (13)	0.0578 (3)
H8	−0.0224	0.6001	1.0842	0.069*
C9	−0.2166 (2)	0.7646 (2)	0.99655 (15)	0.0607 (4)
C10	−0.26237 (16)	0.9274 (2)	0.89053 (15)	0.0578 (3)
H10	−0.3684	0.9682	0.8744	0.069*
C11	−0.15446 (14)	1.03022 (16)	0.80857 (13)	0.0477 (3)
H11	−0.1887	1.1378	0.7378	0.057*
C12	−0.3384 (3)	0.6570 (3)	1.0887 (2)	0.0937 (7)
H12A	−0.3812	0.6747	1.1800	0.141*
H12B	−0.2888	0.5422	1.1161	0.141*
H12C	−0.4221	0.6860	1.0283	0.141*
C13	0.06416 (15)	1.25034 (16)	0.65162 (14)	0.0490 (3)
H13A	0.1413	1.3133	0.6403	0.059*
H13B	−0.0361	1.2966	0.6958	0.059*
C14	0.04568 (16)	1.26957 (17)	0.49896 (14)	0.0538 (3)
C15	0.0333 (2)	1.2781 (2)	0.37825 (17)	0.0708 (4)
H15	0.028 (3)	1.283 (3)	0.274 (3)	0.110 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0400 (4)	0.0548 (5)	0.0483 (4)	−0.0048 (4)	−0.0038 (3)	−0.0255 (4)
O2	0.0676 (6)	0.0685 (7)	0.1059 (8)	0.0071 (5)	−0.0089 (5)	−0.0544 (7)
O3	0.0662 (6)	0.0721 (7)	0.0758 (7)	0.0075 (5)	−0.0223 (5)	−0.0222 (6)
N1	0.0418 (5)	0.0443 (5)	0.0443 (5)	−0.0058 (4)	−0.0006 (4)	−0.0212 (4)
N2	0.0455 (6)	0.0521 (6)	0.0673 (7)	−0.0054 (5)	−0.0025 (5)	−0.0242 (6)
C1	0.0454 (6)	0.0623 (8)	0.0584 (7)	−0.0062 (5)	−0.0061 (5)	−0.0377 (7)
C2	0.0375 (5)	0.0527 (7)	0.0491 (6)	−0.0059 (5)	−0.0017 (4)	−0.0268 (5)
C3	0.0492 (6)	0.0617 (8)	0.0574 (7)	0.0005 (5)	−0.0122 (5)	−0.0350 (6)
C4	0.0519 (6)	0.0601 (8)	0.0551 (7)	−0.0056 (5)	−0.0036 (5)	−0.0349 (6)
C5	0.0404 (6)	0.0490 (7)	0.0542 (7)	−0.0088 (5)	0.0016 (5)	−0.0264 (6)
C6	0.0467 (6)	0.0439 (6)	0.0341 (5)	−0.0055 (5)	−0.0022 (4)	−0.0228 (5)
C7	0.0572 (7)	0.0450 (6)	0.0386 (6)	−0.0025 (5)	−0.0077 (5)	−0.0188 (5)
C8	0.0892 (10)	0.0459 (7)	0.0386 (6)	−0.0181 (7)	−0.0033 (6)	−0.0172 (5)
C9	0.0817 (10)	0.0670 (9)	0.0450 (6)	−0.0349 (8)	0.0080 (6)	−0.0289 (6)
C10	0.0511 (7)	0.0743 (9)	0.0558 (7)	−0.0192 (6)	0.0012 (5)	−0.0333 (7)
C11	0.0482 (7)	0.0466 (6)	0.0453 (6)	−0.0046 (5)	−0.0058 (5)	−0.0189 (5)
C12	0.1217 (16)	0.1020 (16)	0.0717 (10)	−0.0712 (14)	0.0220 (10)	−0.0360 (11)
C13	0.0564 (7)	0.0421 (6)	0.0487 (6)	−0.0104 (5)	−0.0010 (5)	−0.0210 (5)
C14	0.0622 (8)	0.0460 (7)	0.0484 (7)	−0.0119 (6)	−0.0014 (5)	−0.0172 (6)
C15	0.0973 (12)	0.0591 (9)	0.0513 (8)	−0.0110 (8)	−0.0133 (7)	−0.0193 (7)

Geometric parameters (Å, º)

O1—C5	1.3555 (15)	C7—C8	1.3812 (18)
O1—C2	1.3745 (16)	C7—H7	0.9300
O2—N2	1.2328 (16)	C8—C9	1.390 (2)
O3—N2	1.2208 (16)	C8—H8	0.9300
N1—C6	1.3956 (14)	C9—C10	1.395 (2)
N1—C1	1.4432 (16)	C9—C12	1.5175 (19)
N1—C13	1.4584 (16)	C10—C11	1.3859 (18)
N2—C5	1.4276 (19)	C10—H10	0.9300
C1—C2	1.4988 (17)	C11—H11	0.9300
C1—H1A	0.9700	C12—H12A	0.9600
C1—H1B	0.9700	C12—H12B	0.9600
C2—C3	1.3558 (17)	C12—H12C	0.9600
C3—C4	1.416 (2)	C13—C14	1.4737 (18)
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.341 (2)	C13—H13B	0.9700
C4—H4	0.9300	C14—C15	1.183 (2)
C6—C11	1.4017 (17)	C15—H15	1.02 (2)
C6—C7	1.4017 (17)
C5—O1—C2	105.10 (10)	C8—C7—H7	119.7
C6—N1—C1	120.36 (10)	C6—C7—H7	119.7
C6—N1—C13	120.47 (10)	C7—C8—C9	122.24 (14)
C1—N1—C13	118.57 (9)	C7—C8—H8	118.9
O3—N2—O2	124.40 (14)	C9—C8—H8	118.9
O3—N2—C5	119.20 (12)	C8—C9—C10	116.94 (12)
O2—N2—C5	116.39 (13)	C8—C9—C12	122.35 (18)
N1—C1—C2	113.50 (9)	C10—C9—C12	120.70 (18)
N1—C1—H1A	108.9	C11—C10—C9	121.90 (14)
C2—C1—H1A	108.9	C11—C10—H10	119.1
N1—C1—H1B	108.9	C9—C10—H10	119.1
C2—C1—H1B	108.9	C10—C11—C6	120.58 (13)
H1A—C1—H1B	107.7	C10—C11—H11	119.7
C3—C2—O1	109.95 (11)	C6—C11—H11	119.7
C3—C2—C1	134.27 (13)	C9—C12—H12A	109.5
O1—C2—C1	115.77 (10)	C9—C12—H12B	109.5
C2—C3—C4	107.15 (12)	H12A—C12—H12B	109.5
C2—C3—H3	126.4	C9—C12—H12C	109.5
C4—C3—H3	126.4	H12A—C12—H12C	109.5
C5—C4—C3	105.19 (11)	H12B—C12—H12C	109.5
C5—C4—H4	127.4	N1—C13—C14	113.17 (10)
C3—C4—H4	127.4	N1—C13—H13A	108.9
C4—C5—O1	112.60 (12)	C14—C13—H13A	108.9
C4—C5—N2	130.32 (12)	N1—C13—H13B	108.9
O1—C5—N2	116.90 (12)	C14—C13—H13B	108.9
N1—C6—C11	121.51 (11)	H13A—C13—H13B	107.8
N1—C6—C7	120.79 (11)	C13—C14—C15	177.26 (15)
C11—C6—C7	117.70 (10)	C14—C15—H15	177.6 (15)
C8—C7—C6	120.58 (13)
C6—N1—C1—C2	67.03 (14)	C1—N1—C6—C11	−170.99 (10)
C13—N1—C1—C2	−104.13 (12)	C13—N1—C6—C11	0.01 (14)
C5—O1—C2—C3	0.80 (12)	C1—N1—C6—C7	10.00 (14)
C5—O1—C2—C1	179.56 (9)	C13—N1—C6—C7	−179.00 (9)
N1—C1—C2—C3	29.90 (19)	N1—C6—C7—C8	176.02 (9)
N1—C1—C2—O1	−148.47 (10)	C11—C6—C7—C8	−3.02 (16)
O1—C2—C3—C4	−0.44 (14)	C6—C7—C8—C9	1.38 (17)
C1—C2—C3—C4	−178.88 (12)	C7—C8—C9—C10	0.63 (18)
C2—C3—C4—C5	−0.10 (14)	C7—C8—C9—C12	−178.08 (12)
C3—C4—C5—O1	0.63 (13)	C8—C9—C10—C11	−0.93 (18)
C3—C4—C5—N2	175.55 (12)	C12—C9—C10—C11	177.81 (12)
C2—O1—C5—C4	−0.89 (12)	C9—C10—C11—C6	−0.79 (18)
C2—O1—C5—N2	−176.55 (10)	N1—C6—C11—C10	−176.30 (10)
O3—N2—C5—C4	−170.16 (12)	C7—C6—C11—C10	2.74 (16)
O2—N2—C5—C4	9.45 (19)	C6—N1—C13—C14	−79.46 (13)
O3—N2—C5—O1	4.58 (16)	C1—N1—C13—C14	91.70 (12)
O2—N2—C5—O1	−175.82 (9)	N1—C13—C14—C15	−6 (3)