Dimeth­yl[1-(penta­dienyl­idene)eth­yl]amine

In the title mol­ecule, C₉H₁₃N, all bond lengths and angles show normal values. In the crystal structure, weak C—H...π inter­actions link the mol­ecules into centrosymmetric dimers. The crystal packing is further stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.073
• wR factor = 0.155
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

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

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Dimethyl[1-(pentadienylidene)ethyl]amine

Crystal data

C9H13N	F(000) = 296
Mr = 135.20	Dx = 1.132 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.167 (3) Å	Cell parameters from 977 reflections
b = 9.505 (4) Å	θ = 2.8–22.6°
c = 11.647 (4) Å	µ = 0.07 mm^−1
β = 90.423 (5)°	T = 213 K
V = 793.4 (5) Å^3	Block, light-yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Siemens SMART CCD area-detector diffractometer	1392 independent reflections
Radiation source: fine-focus sealed tube	1191 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→8
Tmin = 0.980, Tmax = 0.987	k = −11→10
3179 measured reflections	l = −13→11

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.21	w = 1/[σ^2(Fo^2) + (0.0382P)^2 + 0.5049P] where P = (Fo^2 + 2Fc^2)/3
1392 reflections	(Δ/σ)max < 0.001
94 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.14 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N1	0.3040 (3)	1.1281 (2)	0.1573 (2)	0.0444 (6)
C7	0.2579 (4)	1.0806 (3)	−0.0418 (2)	0.0449 (7)
H7A	0.1468	1.1353	−0.0538	0.067*
H7B	0.2568	1.0012	−0.0927	0.067*
H7C	0.3654	1.1377	−0.0570	0.067*
C6	0.2651 (3)	1.0301 (3)	0.0803 (2)	0.0392 (7)
C1	0.2298 (3)	0.8876 (3)	0.1066 (2)	0.0370 (6)
C2	0.2253 (4)	0.7788 (3)	0.0218 (2)	0.0423 (7)
H2	0.2548	0.7898	−0.0553	0.051*
C3	0.1713 (4)	0.6574 (3)	0.0720 (3)	0.0510 (8)
H3	0.1599	0.5708	0.0355	0.061*
C4	0.1350 (4)	0.6840 (3)	0.1891 (3)	0.0523 (8)
H4	0.0928	0.6183	0.2421	0.063*
C5	0.1721 (4)	0.8223 (3)	0.2113 (2)	0.0453 (7)
H5	0.1616	0.8664	0.2822	0.054*
C9	0.2993 (5)	1.2787 (3)	0.1312 (3)	0.0590 (9)
H9A	0.4182	1.3074	0.1017	0.088*
H9B	0.2728	1.3306	0.1999	0.088*
H9C	0.2040	1.2968	0.0748	0.088*
C8	0.3605 (4)	1.0957 (3)	0.2762 (2)	0.0566 (9)
H8A	0.2542	1.1029	0.3255	0.085*
H8B	0.4546	1.1612	0.3008	0.085*
H8C	0.4097	1.0019	0.2797	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0392 (13)	0.0352 (13)	0.0588 (15)	0.0017 (10)	−0.0024 (11)	−0.0064 (11)
C7	0.0408 (15)	0.0464 (16)	0.0474 (16)	−0.0046 (13)	−0.0013 (13)	0.0095 (13)
C6	0.0255 (13)	0.0441 (15)	0.0478 (16)	0.0046 (12)	0.0005 (11)	−0.0030 (12)
C1	0.0290 (13)	0.0347 (14)	0.0472 (16)	0.0023 (11)	−0.0017 (11)	−0.0005 (11)
C2	0.0435 (16)	0.0417 (15)	0.0417 (15)	0.0037 (13)	−0.0037 (12)	−0.0028 (12)
C3	0.0519 (18)	0.0336 (15)	0.067 (2)	0.0004 (13)	−0.0152 (15)	−0.0040 (13)
C4	0.0453 (17)	0.0485 (18)	0.0630 (19)	−0.0055 (14)	−0.0073 (14)	0.0201 (15)
C5	0.0405 (16)	0.0515 (17)	0.0437 (16)	0.0024 (13)	−0.0038 (12)	0.0020 (13)
C9	0.059 (2)	0.0349 (16)	0.083 (2)	−0.0021 (14)	0.0003 (17)	−0.0045 (15)
C8	0.0575 (19)	0.060 (2)	0.0521 (18)	0.0103 (16)	−0.0170 (15)	−0.0179 (15)

Geometric parameters (Å, º)

N1—C6	1.322 (3)	C3—C4	1.413 (4)
N1—C9	1.463 (4)	C3—H3	0.9300
N1—C8	1.472 (3)	C4—C5	1.365 (4)
C7—C6	1.501 (3)	C4—H4	0.9300
C7—H7A	0.9600	C5—H5	0.9300
C7—H7B	0.9600	C9—H9A	0.9600
C7—H7C	0.9600	C9—H9B	0.9600
C6—C1	1.412 (4)	C9—H9C	0.9600
C1—C2	1.430 (4)	C8—H8A	0.9600
C1—C5	1.432 (4)	C8—H8B	0.9600
C2—C3	1.351 (4)	C8—H8C	0.9600
C2—H2	0.9300
C6—N1—C9	122.9 (2)	C4—C3—H3	125.7
C6—N1—C8	123.1 (2)	C5—C4—C3	108.5 (3)
C9—N1—C8	114.0 (2)	C5—C4—H4	125.7
C6—C7—H7A	109.5	C3—C4—H4	125.7
C6—C7—H7B	109.5	C4—C5—C1	108.2 (3)
H7A—C7—H7B	109.5	C4—C5—H5	125.9
C6—C7—H7C	109.5	C1—C5—H5	125.9
H7A—C7—H7C	109.5	N1—C9—H9A	109.5
H7B—C7—H7C	109.5	N1—C9—H9B	109.5
N1—C6—C1	124.5 (2)	H9A—C9—H9B	109.5
N1—C6—C7	115.0 (2)	N1—C9—H9C	109.5
C1—C6—C7	120.5 (2)	H9A—C9—H9C	109.5
C6—C1—C2	123.2 (2)	H9B—C9—H9C	109.5
C6—C1—C5	130.8 (2)	N1—C8—H8A	109.5
C2—C1—C5	105.6 (2)	N1—C8—H8B	109.5
C3—C2—C1	108.9 (2)	H8A—C8—H8B	109.5
C3—C2—H2	125.6	N1—C8—H8C	109.5
C1—C2—H2	125.6	H8A—C8—H8C	109.5
C2—C3—C4	108.7 (2)	H8B—C8—H8C	109.5
C2—C3—H3	125.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cg^i	0.96	2.68	3.615 (3)	166

Symmetry code: (i) −x, −y+2, −z.