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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013068/qd0041sup1.cif
Contains datablocks I, PROPINIL

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013068/qd0041Isup2.hkl
Contains datablock I

CCDC reference: 153947

Computing details top

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 top
Crystal data top
C15H14N2O3Z = 2
Mr = 270.28F(000) = 284
Triclinic, P1Dx = 1.314 Mg m3
a = 8.8490 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.2060 (13) ÅCell parameters from 57 reflections
c = 9.8438 (19) Åθ = 8–17.8°
α = 63.196 (14)°µ = 0.09 mm1
β = 76.908 (15)°T = 293 K
γ = 73.937 (13)°Prism, pale orange
V = 683.0 (2) Å30.69 × 0.45 × 0.14 mm
Data collection top
Philips PW1100 updated by Stoe
diffractometer
Rint = 0.105
Radiation source: fine-focus sealed tubeθmax = 29.0°, θmin = 3.0°
Graphite monochromatorh = 1212
ω scansk = 1212
7040 measured reflectionsl = 1313
3520 independent reflections5 standard reflections every 90 min
1997 reflections with I > 2σ(I) intensity decay: 7.2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: geom and dmap
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 0.97Calculated w = 1/[σ2(Fo2) + (0.0189P)2]
where P = (Fo2 + 2Fc2)/3
3520 reflections(Δ/σ)max < 0.001
186 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.16 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.47394 (9)0.77179 (11)0.74520 (9)0.0474 (2)
O20.67701 (14)0.47179 (16)0.61158 (15)0.0784 (3)
O30.69057 (13)0.49415 (15)0.81856 (14)0.0769 (3)
N10.11488 (11)1.07782 (13)0.75658 (10)0.0438 (2)
N20.63536 (13)0.54186 (15)0.69909 (14)0.0569 (3)
C10.28225 (14)1.01103 (18)0.76444 (15)0.0515 (3)
H1A0.30050.94980.87120.062*
H1B0.33801.10230.71950.062*
C20.34977 (13)0.89850 (16)0.68373 (13)0.0455 (3)
C30.31406 (15)0.88957 (18)0.56119 (15)0.0536 (3)
H30.23430.96070.50060.064*
C40.42096 (16)0.75164 (18)0.54272 (15)0.0532 (3)
H40.42590.71360.46850.064*
C50.51347 (14)0.68762 (17)0.65516 (14)0.0473 (3)
C60.00588 (13)0.97352 (14)0.83140 (11)0.0402 (2)
C70.05328 (16)0.80830 (16)0.93425 (12)0.0477 (3)
H70.15970.76550.94820.057*
C80.05664 (19)0.70851 (18)1.01507 (13)0.0578 (3)
H80.02240.60011.08420.069*
C90.2166 (2)0.7646 (2)0.99655 (15)0.0607 (4)
C100.26237 (16)0.9274 (2)0.89053 (15)0.0578 (3)
H100.36840.96820.87440.069*
C110.15446 (14)1.03022 (16)0.80857 (13)0.0477 (3)
H110.18871.13780.73780.057*
C120.3384 (3)0.6570 (3)1.0887 (2)0.0937 (7)
H12A0.38120.67471.18000.141*
H12B0.28880.54221.11610.141*
H12C0.42210.68601.02830.141*
C130.06416 (15)1.25034 (16)0.65162 (14)0.0490 (3)
H13A0.14131.31330.64030.059*
H13B0.03611.29660.69580.059*
C140.04568 (16)1.26957 (17)0.49896 (14)0.0538 (3)
C150.0333 (2)1.2781 (2)0.37825 (17)0.0708 (4)
H150.028 (3)1.283 (3)0.274 (3)0.110 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0400 (4)0.0548 (5)0.0483 (4)0.0048 (4)0.0038 (3)0.0255 (4)
O20.0676 (6)0.0685 (7)0.1059 (8)0.0071 (5)0.0089 (5)0.0544 (7)
O30.0662 (6)0.0721 (7)0.0758 (7)0.0075 (5)0.0223 (5)0.0222 (6)
N10.0418 (5)0.0443 (5)0.0443 (5)0.0058 (4)0.0006 (4)0.0212 (4)
N20.0455 (6)0.0521 (6)0.0673 (7)0.0054 (5)0.0025 (5)0.0242 (6)
C10.0454 (6)0.0623 (8)0.0584 (7)0.0062 (5)0.0061 (5)0.0377 (7)
C20.0375 (5)0.0527 (7)0.0491 (6)0.0059 (5)0.0017 (4)0.0268 (5)
C30.0492 (6)0.0617 (8)0.0574 (7)0.0005 (5)0.0122 (5)0.0350 (6)
C40.0519 (6)0.0601 (8)0.0551 (7)0.0056 (5)0.0036 (5)0.0349 (6)
C50.0404 (6)0.0490 (7)0.0542 (7)0.0088 (5)0.0016 (5)0.0264 (6)
C60.0467 (6)0.0439 (6)0.0341 (5)0.0055 (5)0.0022 (4)0.0228 (5)
C70.0572 (7)0.0450 (6)0.0386 (6)0.0025 (5)0.0077 (5)0.0188 (5)
C80.0892 (10)0.0459 (7)0.0386 (6)0.0181 (7)0.0033 (6)0.0172 (5)
C90.0817 (10)0.0670 (9)0.0450 (6)0.0349 (8)0.0080 (6)0.0289 (6)
C100.0511 (7)0.0743 (9)0.0558 (7)0.0192 (6)0.0012 (5)0.0333 (7)
C110.0482 (7)0.0466 (6)0.0453 (6)0.0046 (5)0.0058 (5)0.0189 (5)
C120.1217 (16)0.1020 (16)0.0717 (10)0.0712 (14)0.0220 (10)0.0360 (11)
C130.0564 (7)0.0421 (6)0.0487 (6)0.0104 (5)0.0010 (5)0.0210 (5)
C140.0622 (8)0.0460 (7)0.0484 (7)0.0119 (6)0.0014 (5)0.0172 (6)
C150.0973 (12)0.0591 (9)0.0513 (8)0.0110 (8)0.0133 (7)0.0193 (7)
Geometric parameters (Å, º) top
O1—C51.3555 (15)C7—C81.3812 (18)
O1—C21.3745 (16)C7—H70.9300
O2—N21.2328 (16)C8—C91.390 (2)
O3—N21.2208 (16)C8—H80.9300
N1—C61.3956 (14)C9—C101.395 (2)
N1—C11.4432 (16)C9—C121.5175 (19)
N1—C131.4584 (16)C10—C111.3859 (18)
N2—C51.4276 (19)C10—H100.9300
C1—C21.4988 (17)C11—H110.9300
C1—H1A0.9700C12—H12A0.9600
C1—H1B0.9700C12—H12B0.9600
C2—C31.3558 (17)C12—H12C0.9600
C3—C41.416 (2)C13—C141.4737 (18)
C3—H30.9300C13—H13A0.9700
C4—C51.341 (2)C13—H13B0.9700
C4—H40.9300C14—C151.183 (2)
C6—C111.4017 (17)C15—H151.02 (2)
C6—C71.4017 (17)
C5—O1—C2105.10 (10)C8—C7—H7119.7
C6—N1—C1120.36 (10)C6—C7—H7119.7
C6—N1—C13120.47 (10)C7—C8—C9122.24 (14)
C1—N1—C13118.57 (9)C7—C8—H8118.9
O3—N2—O2124.40 (14)C9—C8—H8118.9
O3—N2—C5119.20 (12)C8—C9—C10116.94 (12)
O2—N2—C5116.39 (13)C8—C9—C12122.35 (18)
N1—C1—C2113.50 (9)C10—C9—C12120.70 (18)
N1—C1—H1A108.9C11—C10—C9121.90 (14)
C2—C1—H1A108.9C11—C10—H10119.1
N1—C1—H1B108.9C9—C10—H10119.1
C2—C1—H1B108.9C10—C11—C6120.58 (13)
H1A—C1—H1B107.7C10—C11—H11119.7
C3—C2—O1109.95 (11)C6—C11—H11119.7
C3—C2—C1134.27 (13)C9—C12—H12A109.5
O1—C2—C1115.77 (10)C9—C12—H12B109.5
C2—C3—C4107.15 (12)H12A—C12—H12B109.5
C2—C3—H3126.4C9—C12—H12C109.5
C4—C3—H3126.4H12A—C12—H12C109.5
C5—C4—C3105.19 (11)H12B—C12—H12C109.5
C5—C4—H4127.4N1—C13—C14113.17 (10)
C3—C4—H4127.4N1—C13—H13A108.9
C4—C5—O1112.60 (12)C14—C13—H13A108.9
C4—C5—N2130.32 (12)N1—C13—H13B108.9
O1—C5—N2116.90 (12)C14—C13—H13B108.9
N1—C6—C11121.51 (11)H13A—C13—H13B107.8
N1—C6—C7120.79 (11)C13—C14—C15177.26 (15)
C11—C6—C7117.70 (10)C14—C15—H15177.6 (15)
C8—C7—C6120.58 (13)
C6—N1—C1—C267.03 (14)C1—N1—C6—C11170.99 (10)
C13—N1—C1—C2104.13 (12)C13—N1—C6—C110.01 (14)
C5—O1—C2—C30.80 (12)C1—N1—C6—C710.00 (14)
C5—O1—C2—C1179.56 (9)C13—N1—C6—C7179.00 (9)
N1—C1—C2—C329.90 (19)N1—C6—C7—C8176.02 (9)
N1—C1—C2—O1148.47 (10)C11—C6—C7—C83.02 (16)
O1—C2—C3—C40.44 (14)C6—C7—C8—C91.38 (17)
C1—C2—C3—C4178.88 (12)C7—C8—C9—C100.63 (18)
C2—C3—C4—C50.10 (14)C7—C8—C9—C12178.08 (12)
C3—C4—C5—O10.63 (13)C8—C9—C10—C110.93 (18)
C3—C4—C5—N2175.55 (12)C12—C9—C10—C11177.81 (12)
C2—O1—C5—C40.89 (12)C9—C10—C11—C60.79 (18)
C2—O1—C5—N2176.55 (10)N1—C6—C11—C10176.30 (10)
O3—N2—C5—C4170.16 (12)C7—C6—C11—C102.74 (16)
O2—N2—C5—C49.45 (19)C6—N1—C13—C1479.46 (13)
O3—N2—C5—O14.58 (16)C1—N1—C13—C1491.70 (12)
O2—N2—C5—O1175.82 (9)N1—C13—C14—C156 (3)
 

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