2-Cyano-3-di­methyl­amino-N-(2,5-dimethyl­phenyl)­acryl­amide

In the title compound, C₁₄H₁₇N₃O, the dihedral angle between the benzene ring and amido group is 4.1 (1)°. The molecular structure is stabilized by intramolecular C—H...O and N—H...N hydrogen bonds, and the packing of the mol­ecules in the solid state is stabilized by weak intermolecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.058
• wR factor = 0.168
• Data-to-parameter ratio = 19.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(10)  -   C(11)  =       1.42 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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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: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2-cyano-3-dimethylamino-N-(2,5-methylphenyl)acrylamide

Crystal data

C14H17N3O	F(000) = 520
Mr = 243.31	Dx = 1.210 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3509 reflections
a = 9.9315 (2) Å	θ = 2.5–28.3°
b = 11.8940 (4) Å	µ = 0.08 mm^−1
c = 11.3979 (4) Å	T = 293 K
β = 97.079 (14)°	Plate, colourless
V = 1336.12 (8) Å^3	0.46 × 0.32 × 0.24 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	2001 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 28.3°, θmin = 2.5°
ω scans	h = −12→13
9076 measured reflections	k = −13→15
3291 independent reflections	l = −10→15

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.168	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0822P)^2 + 0.114P] where P = (Fo^2 + 2Fc^2)/3
3291 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.21 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.

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
C1	0.38358 (17)	0.50888 (14)	0.66130 (15)	0.0450 (4)
C2	0.45239 (19)	0.54894 (16)	0.76825 (16)	0.0535 (5)
C3	0.3961 (2)	0.64001 (18)	0.82077 (19)	0.0685 (6)
H3	0.4393	0.6675	0.8920	0.082*
C4	0.2782 (3)	0.69105 (18)	0.7708 (2)	0.0705 (6)
H4	0.2439	0.7524	0.8082	0.085*
C5	0.2106 (2)	0.65193 (17)	0.66578 (19)	0.0606 (5)
C6	0.26400 (19)	0.56044 (15)	0.61184 (16)	0.0518 (5)
H6	0.2190	0.5330	0.5412	0.062*
N7	0.44063 (14)	0.41613 (12)	0.60818 (12)	0.0474 (4)
H7	0.5174	0.3935	0.6435	0.057*
C8	0.39277 (17)	0.35672 (14)	0.50932 (15)	0.0454 (4)
O9	0.28856 (15)	0.38084 (14)	0.44681 (13)	0.0780 (5)
C10	0.47713 (16)	0.25864 (14)	0.48407 (15)	0.0435 (4)
C11	0.5921 (2)	0.23470 (15)	0.56674 (17)	0.0527 (5)
N12	0.6826 (2)	0.22280 (18)	0.63869 (19)	0.0839 (6)
C13	0.43875 (17)	0.20134 (14)	0.38065 (16)	0.0460 (4)
H13	0.3627	0.2305	0.3350	0.055*
N14	0.49174 (15)	0.11173 (13)	0.33516 (13)	0.0530 (4)
C15	0.4362 (2)	0.0697 (2)	0.2195 (2)	0.0771 (7)
H15A	0.3611	0.1159	0.1880	0.116*
H15B	0.4058	−0.0063	0.2269	0.116*
H15C	0.5051	0.0718	0.1674	0.116*
C16	0.6128 (2)	0.05418 (19)	0.3892 (2)	0.0690 (6)
H16A	0.6916	0.0974	0.3770	0.103*
H16B	0.6182	−0.0186	0.3537	0.103*
H16C	0.6086	0.0458	0.4724	0.103*
C17	0.5851 (2)	0.4988 (2)	0.8222 (2)	0.0729 (6)
H17A	0.6546	0.5165	0.7736	0.109*
H17B	0.5759	0.4186	0.8273	0.109*
H17C	0.6092	0.5292	0.8999	0.109*
C18	0.0825 (3)	0.7079 (2)	0.6096 (3)	0.0878 (8)
H18A	0.1053	0.7685	0.5600	0.132*
H18B	0.0330	0.7369	0.6703	0.132*
H18C	0.0276	0.6540	0.5628	0.132*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0514 (10)	0.0394 (9)	0.0461 (10)	−0.0056 (8)	0.0136 (8)	0.0016 (7)
C2	0.0607 (11)	0.0475 (10)	0.0532 (11)	−0.0154 (9)	0.0109 (9)	−0.0008 (8)
C3	0.0890 (15)	0.0572 (12)	0.0618 (13)	−0.0178 (12)	0.0188 (11)	−0.0154 (10)
C4	0.0928 (16)	0.0506 (12)	0.0739 (15)	0.0019 (11)	0.0336 (13)	−0.0090 (10)
C5	0.0725 (13)	0.0473 (11)	0.0667 (13)	0.0075 (9)	0.0277 (11)	0.0050 (9)
C6	0.0602 (11)	0.0456 (10)	0.0520 (10)	0.0047 (8)	0.0160 (8)	0.0034 (8)
N7	0.0472 (8)	0.0448 (8)	0.0489 (9)	0.0057 (6)	0.0006 (6)	−0.0026 (6)
C8	0.0462 (9)	0.0441 (9)	0.0457 (10)	0.0016 (8)	0.0050 (7)	0.0004 (8)
O9	0.0661 (9)	0.0825 (10)	0.0778 (10)	0.0324 (8)	−0.0213 (8)	−0.0285 (8)
C10	0.0421 (9)	0.0414 (9)	0.0469 (10)	0.0008 (7)	0.0057 (7)	0.0031 (7)
C11	0.0564 (11)	0.0454 (10)	0.0555 (11)	0.0085 (8)	0.0038 (9)	−0.0015 (8)
N12	0.0850 (13)	0.0777 (13)	0.0804 (14)	0.0254 (11)	−0.0242 (11)	−0.0089 (10)
C13	0.0422 (9)	0.0446 (10)	0.0517 (10)	0.0027 (7)	0.0075 (7)	0.0003 (8)
N14	0.0535 (9)	0.0484 (8)	0.0578 (10)	0.0033 (7)	0.0100 (7)	−0.0072 (7)
C15	0.0754 (14)	0.0796 (16)	0.0745 (15)	0.0083 (12)	0.0013 (12)	−0.0292 (12)
C16	0.0690 (13)	0.0619 (13)	0.0766 (14)	0.0214 (10)	0.0115 (11)	−0.0057 (11)
C17	0.0722 (13)	0.0700 (14)	0.0723 (14)	−0.0182 (12)	−0.0084 (11)	−0.0062 (11)
C18	0.0939 (17)	0.0731 (16)	0.1008 (19)	0.0355 (14)	0.0297 (14)	0.0050 (13)

Geometric parameters (Å, º)

C1—C6	1.393 (2)	C11—N12	1.148 (2)
C1—C2	1.405 (2)	C13—N14	1.323 (2)
C1—N7	1.410 (2)	C13—H13	0.93
C2—C3	1.388 (3)	N14—C15	1.453 (2)
C2—C17	1.507 (3)	N14—C16	1.453 (2)
C3—C4	1.378 (3)	C15—H15A	0.96
C3—H3	0.93	C15—H15B	0.96
C4—C5	1.379 (3)	C15—H15C	0.96
C4—H4	0.93	C16—H16A	0.96
C5—C6	1.387 (3)	C16—H16B	0.96
C5—C18	1.507 (3)	C16—H16C	0.96
C6—H6	0.93	C17—H17A	0.96
N7—C8	1.365 (2)	C17—H17B	0.96
N7—H7	0.86	C17—H17C	0.96
C8—O9	1.216 (2)	C18—H18A	0.96
C8—C10	1.485 (2)	C18—H18B	0.96
C10—C13	1.374 (2)	C18—H18C	0.96
C10—C11	1.417 (3)
C6—C1—C2	120.08 (17)	N14—C13—H13	114.6
C6—C1—N7	122.57 (16)	C10—C13—H13	114.6
C2—C1—N7	117.35 (16)	C13—N14—C15	120.53 (16)
C3—C2—C1	117.38 (18)	C13—N14—C16	124.21 (16)
C3—C2—C17	120.79 (18)	C15—N14—C16	115.07 (16)
C1—C2—C17	121.79 (18)	N14—C15—H15A	109.5
C4—C3—C2	122.2 (2)	N14—C15—H15B	109.5
C4—C3—H3	118.9	H15A—C15—H15B	109.5
C2—C3—H3	118.9	N14—C15—H15C	109.5
C3—C4—C5	120.5 (2)	H15A—C15—H15C	109.5
C3—C4—H4	119.7	H15B—C15—H15C	109.5
C5—C4—H4	119.7	N14—C16—H16A	109.5
C4—C5—C6	118.5 (2)	N14—C16—H16B	109.5
C4—C5—C18	121.0 (2)	H16A—C16—H16B	109.5
C6—C5—C18	120.5 (2)	N14—C16—H16C	109.5
C5—C6—C1	121.31 (19)	H16A—C16—H16C	109.5
C5—C6—H6	119.3	H16B—C16—H16C	109.5
C1—C6—H6	119.3	C2—C17—H17A	109.5
C8—N7—C1	129.93 (14)	C2—C17—H17B	109.5
C8—N7—H7	115.0	H17A—C17—H17B	109.5
C1—N7—H7	115.0	C2—C17—H17C	109.5
O9—C8—N7	123.11 (16)	H17A—C17—H17C	109.5
O9—C8—C10	122.10 (16)	H17B—C17—H17C	109.5
N7—C8—C10	114.79 (14)	C5—C18—H18A	109.5
C13—C10—C11	125.91 (16)	C5—C18—H18B	109.5
C13—C10—C8	116.89 (15)	H18A—C18—H18B	109.5
C11—C10—C8	117.17 (15)	C5—C18—H18C	109.5
N12—C11—C10	174.5 (2)	H18A—C18—H18C	109.5
N14—C13—C10	130.86 (16)	H18B—C18—H18C	109.5
C6—C1—C2—C3	0.2 (3)	C6—C1—N7—C8	−4.0 (3)
N7—C1—C2—C3	−179.80 (15)	C2—C1—N7—C8	176.02 (16)
C6—C1—C2—C17	−177.38 (17)	C1—N7—C8—O9	3.1 (3)
N7—C1—C2—C17	2.6 (3)	C1—N7—C8—C10	−176.25 (15)
C1—C2—C3—C4	−0.7 (3)	O9—C8—C10—C13	5.5 (3)
C17—C2—C3—C4	176.9 (2)	N7—C8—C10—C13	−175.17 (15)
C2—C3—C4—C5	0.6 (3)	O9—C8—C10—C11	−176.38 (18)
C3—C4—C5—C6	0.0 (3)	N7—C8—C10—C11	2.9 (2)
C3—C4—C5—C18	−179.3 (2)	C11—C10—C13—N14	2.8 (3)
C4—C5—C6—C1	−0.4 (3)	C8—C10—C13—N14	−179.30 (17)
C18—C5—C6—C1	178.84 (18)	C10—C13—N14—C15	−176.65 (19)
C2—C1—C6—C5	0.3 (3)	C10—C13—N14—C16	−1.9 (3)
N7—C1—C6—C5	−179.66 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···N12	0.86	2.62	3.313 (2)	139
C6—H6···O9	0.93	2.26	2.876 (2)	124
C13—H13···O9	0.93	2.37	2.762 (2)	105
C15—H15A···N12^i	0.96	2.63	3.566 (3)	166

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.