N-(2-Cyano­propan-2-yl)isobutyramide

The title compound, C₈H₁₄N₂O, is stabilized in the solid state as a keto tautomer. The asymmetric unit contains two mol­ecules with different conformations. In the crystal structure, inter­molecular N—H...O hydrogen bonds of moderate strength link the mol­ecules into chains along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.052
• wR factor = 0.152
• Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C29

Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       3.00 Sigma
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               1785
           Count of symmetry unique reflns         1785
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

N-(2-Cyanopropan-2-yl)-isobutyramide

Crystal data

C8H14N2O	Dx = 1.043 Mg m^−3
Mr = 154.21	Melting point: 373 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 60 reflections
a = 11.452 (3) Å	θ = 4.7–11.4°
b = 8.859 (2) Å	µ = 0.07 mm^−1
c = 19.352 (8) Å	T = 296 K
V = 1963.3 (10) Å^3	Plate, colourless
Z = 8	0.60 × 0.44 × 0.14 mm
F(000) = 672

Data collection

Bruker P4 diffractometer	Rint = 0.025
Radiation source: fine-focus sealed tube, FN4	θmax = 25.0°, θmin = 2.1°
Graphite monochromator	h = −1→13
ω scans	k = −10→2
2383 measured reflections	l = −1→22
1785 independent reflections	3 standard reflections every 97 reflections
1157 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: see text
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.0855P)^2 + 0.0673P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
1785 reflections	Δρmax = 0.21 e Å^−3
216 parameters	Δρmin = −0.13 e Å^−3
1 restraint	Extinction correction: SHELXTL-Plus, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0054 (18)

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
C1	0.6906 (5)	0.6648 (7)	0.3666 (3)	0.1062 (19)
H1A	0.6808	0.6063	0.4080	0.159*
H1B	0.7422	0.7478	0.3757	0.159*
H1C	0.7232	0.6023	0.3310	0.159*
C2	0.5709 (4)	0.7257 (5)	0.3429 (2)	0.0712 (12)
C3	0.5819 (6)	0.8274 (6)	0.2790 (3)	0.110 (2)
H3A	0.5057	0.8605	0.2650	0.165*
H3B	0.6177	0.7718	0.2421	0.165*
H3C	0.6292	0.9136	0.2901	0.165*
C4	0.5223 (5)	0.8171 (6)	0.3998 (3)	0.0798 (14)
N5	0.4894 (5)	0.8963 (6)	0.4430 (3)	0.1157 (18)
N6	0.4914 (4)	0.6035 (4)	0.32595 (18)	0.0650 (10)
H6	0.484 (4)	0.595 (6)	0.284 (3)	0.089 (16)*
C7	0.4483 (4)	0.5044 (5)	0.3713 (2)	0.0631 (12)
O8	0.4671 (3)	0.5205 (4)	0.43400 (15)	0.0865 (12)
C9	0.3803 (4)	0.3749 (4)	0.3429 (2)	0.0674 (11)
H9A	0.3484	0.4042	0.2978	0.081*
C10	0.2803 (5)	0.3308 (7)	0.3898 (3)	0.1086 (18)
H10A	0.2292	0.4156	0.3959	0.163*
H10B	0.3106	0.3001	0.4339	0.163*
H10C	0.2377	0.2487	0.3695	0.163*
C11	0.4620 (5)	0.2414 (6)	0.3327 (3)	0.0980 (17)
H11A	0.5242	0.2697	0.3020	0.147*
H11B	0.4193	0.1585	0.3131	0.147*
H11C	0.4940	0.2117	0.3765	0.147*
C21	0.4397 (6)	0.7928 (6)	0.6342 (3)	0.1014 (18)
H21A	0.4950	0.7616	0.6686	0.152*
H21B	0.3875	0.8662	0.6537	0.152*
H21C	0.4804	0.8367	0.5958	0.152*
C22	0.3696 (4)	0.6556 (5)	0.6095 (2)	0.0654 (11)
C23	0.2812 (4)	0.6991 (7)	0.5543 (3)	0.0918 (16)
H23A	0.2401	0.6106	0.5392	0.138*
H23B	0.3211	0.7438	0.5157	0.138*
H23C	0.2266	0.7703	0.5731	0.138*
C24	0.3049 (5)	0.5901 (5)	0.6686 (2)	0.0796 (14)
N25	0.2477 (5)	0.5483 (7)	0.7123 (3)	0.1213 (19)
N26	0.4472 (4)	0.5409 (5)	0.58085 (19)	0.0668 (11)
H26	0.448 (5)	0.530 (6)	0.540 (4)	0.096 (19)*
C27	0.5242 (4)	0.4595 (5)	0.6171 (2)	0.0672 (12)
O28	0.5324 (3)	0.4724 (4)	0.68029 (15)	0.0870 (12)
C29	0.5978 (5)	0.3488 (6)	0.5768 (2)	0.0822 (15)
H29A	0.6062	0.3887	0.5298	0.099*
C30	0.5422 (6)	0.2013 (9)	0.5715 (6)	0.160 (4)
H30A	0.5824	0.1416	0.5376	0.240*
H30B	0.4622	0.2138	0.5578	0.240*
H30C	0.5454	0.1515	0.6155	0.240*
C31	0.7177 (6)	0.3348 (10)	0.6068 (6)	0.168 (4)
H31A	0.7700	0.2956	0.5724	0.252*
H31B	0.7156	0.2676	0.6457	0.252*
H31C	0.7444	0.4323	0.6215	0.252*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.097 (4)	0.115 (4)	0.107 (4)	−0.014 (3)	−0.005 (3)	−0.033 (4)
C2	0.085 (3)	0.077 (3)	0.051 (2)	−0.020 (3)	0.004 (2)	−0.011 (2)
C3	0.169 (5)	0.097 (4)	0.064 (3)	−0.058 (4)	0.018 (4)	0.007 (3)
C4	0.110 (4)	0.069 (3)	0.060 (3)	−0.023 (3)	0.006 (3)	−0.003 (3)
N5	0.173 (5)	0.087 (3)	0.087 (3)	−0.022 (3)	0.031 (3)	−0.027 (3)
N6	0.093 (3)	0.068 (2)	0.0346 (17)	−0.016 (2)	−0.0007 (17)	−0.0029 (18)
C7	0.082 (3)	0.070 (3)	0.038 (2)	0.001 (2)	−0.003 (2)	−0.005 (2)
O8	0.127 (3)	0.092 (2)	0.0401 (17)	−0.017 (2)	−0.0052 (18)	0.0051 (15)
C9	0.077 (3)	0.068 (2)	0.057 (2)	−0.007 (2)	−0.016 (2)	0.003 (2)
C10	0.092 (4)	0.112 (4)	0.121 (4)	−0.020 (3)	0.008 (4)	0.005 (4)
C11	0.093 (4)	0.081 (3)	0.120 (4)	0.002 (3)	−0.013 (3)	−0.025 (3)
C21	0.133 (5)	0.081 (4)	0.090 (4)	0.004 (3)	−0.004 (4)	−0.001 (3)
C22	0.077 (3)	0.066 (2)	0.053 (2)	0.012 (2)	0.010 (2)	0.004 (2)
C23	0.093 (3)	0.109 (4)	0.074 (3)	0.021 (3)	−0.005 (3)	0.023 (3)
C24	0.086 (3)	0.091 (3)	0.062 (3)	0.016 (3)	0.018 (3)	−0.001 (3)
N25	0.129 (4)	0.150 (5)	0.085 (3)	0.031 (4)	0.044 (3)	0.021 (3)
N26	0.085 (3)	0.081 (3)	0.0345 (19)	0.011 (2)	0.0010 (18)	0.0031 (19)
C27	0.084 (3)	0.080 (3)	0.038 (2)	0.005 (3)	−0.005 (2)	0.005 (2)
O28	0.119 (3)	0.102 (2)	0.0404 (17)	0.020 (2)	−0.0096 (18)	0.0075 (17)
C29	0.090 (3)	0.094 (4)	0.062 (3)	0.022 (3)	0.010 (3)	0.000 (3)
C30	0.115 (5)	0.125 (6)	0.239 (11)	−0.014 (5)	0.031 (6)	−0.098 (7)
C31	0.087 (5)	0.142 (6)	0.275 (12)	0.017 (4)	−0.010 (6)	−0.073 (8)

Geometric parameters (Å, º)

C1—C2	1.543 (8)	C21—C22	1.533 (7)
C1—H1A	0.9600	C21—H21A	0.9600
C1—H1B	0.9600	C21—H21B	0.9600
C1—H1C	0.9600	C21—H21C	0.9600
C2—N6	1.453 (6)	C22—N26	1.460 (6)
C2—C4	1.475 (7)	C22—C24	1.481 (7)
C2—C3	1.535 (6)	C22—C23	1.522 (7)
C3—H3A	0.9600	C23—H23A	0.9600
C3—H3B	0.9600	C23—H23B	0.9600
C3—H3C	0.9600	C23—H23C	0.9600
C4—N5	1.156 (6)	C24—N25	1.131 (6)
N6—C7	1.336 (6)	N26—C27	1.337 (6)
N6—H6	0.82 (6)	N26—H26	0.80 (7)
C7—O8	1.241 (5)	C27—O28	1.232 (5)
C7—C9	1.492 (6)	C27—C29	1.511 (7)
C9—C10	1.514 (7)	C29—C30	1.457 (8)
C9—C11	1.521 (7)	C29—C31	1.496 (9)
C9—H9A	0.9800	C29—H29A	0.9800
C10—H10A	0.9600	C30—H30A	0.9600
C10—H10B	0.9600	C30—H30B	0.9600
C10—H10C	0.9600	C30—H30C	0.9600
C11—H11A	0.9600	C31—H31A	0.9600
C11—H11B	0.9600	C31—H31B	0.9600
C11—H11C	0.9600	C31—H31C	0.9600
C2—C1—H1A	109.5	C22—C21—H21A	109.5
C2—C1—H1B	109.5	C22—C21—H21B	109.5
H1A—C1—H1B	109.5	H21A—C21—H21B	109.5
C2—C1—H1C	109.5	C22—C21—H21C	109.5
H1A—C1—H1C	109.5	H21A—C21—H21C	109.5
H1B—C1—H1C	109.5	H21B—C21—H21C	109.5
N6—C2—C4	109.9 (4)	N26—C22—C24	109.0 (4)
N6—C2—C3	107.9 (4)	N26—C22—C23	108.3 (4)
C4—C2—C3	108.0 (4)	C24—C22—C23	108.0 (4)
N6—C2—C1	111.3 (4)	N26—C22—C21	110.6 (4)
C4—C2—C1	107.8 (4)	C24—C22—C21	109.4 (4)
C3—C2—C1	111.8 (5)	C23—C22—C21	111.5 (4)
C2—C3—H3A	109.5	C22—C23—H23A	109.5
C2—C3—H3B	109.5	C22—C23—H23B	109.5
H3A—C3—H3B	109.5	H23A—C23—H23B	109.5
C2—C3—H3C	109.5	C22—C23—H23C	109.5
H3A—C3—H3C	109.5	H23A—C23—H23C	109.5
H3B—C3—H3C	109.5	H23B—C23—H23C	109.5
N5—C4—C2	175.4 (5)	N25—C24—C22	174.0 (6)
C7—N6—C2	125.0 (4)	C27—N26—C22	125.3 (4)
C7—N6—H6	124 (4)	C27—N26—H26	116 (4)
C2—N6—H6	111 (4)	C22—N26—H26	118 (4)
O8—C7—N6	120.2 (4)	O28—C27—N26	121.4 (4)
O8—C7—C9	122.7 (4)	O28—C27—C29	122.0 (4)
N6—C7—C9	117.1 (4)	N26—C27—C29	116.5 (3)
C7—C9—C10	111.8 (4)	C30—C29—C31	110.7 (6)
C7—C9—C11	108.9 (4)	C30—C29—C27	112.0 (5)
C10—C9—C11	110.0 (4)	C31—C29—C27	111.4 (5)
C7—C9—H9A	108.7	C30—C29—H29A	107.5
C10—C9—H9A	108.7	C31—C29—H29A	107.5
C11—C9—H9A	108.7	C27—C29—H29A	107.5
C9—C10—H10A	109.5	C29—C30—H30A	109.5
C9—C10—H10B	109.5	C29—C30—H30B	109.5
H10A—C10—H10B	109.5	H30A—C30—H30B	109.5
C9—C10—H10C	109.5	C29—C30—H30C	109.5
H10A—C10—H10C	109.5	H30A—C30—H30C	109.5
H10B—C10—H10C	109.5	H30B—C30—H30C	109.5
C9—C11—H11A	109.5	C29—C31—H31A	109.5
C9—C11—H11B	109.5	C29—C31—H31B	109.5
H11A—C11—H11B	109.5	H31A—C31—H31B	109.5
C9—C11—H11C	109.5	C29—C31—H31C	109.5
H11A—C11—H11C	109.5	H31A—C31—H31C	109.5
H11B—C11—H11C	109.5	H31B—C31—H31C	109.5
C4—C2—N6—C7	−53.0 (6)	C24—C22—N26—C27	−52.1 (6)
C3—C2—N6—C7	−170.6 (5)	C23—C22—N26—C27	−169.4 (5)
C1—C2—N6—C7	66.4 (6)	C21—C22—N26—C27	68.1 (6)
C2—N6—C7—O8	6.5 (7)	C22—N26—C27—O28	2.8 (8)
C2—N6—C7—C9	−172.3 (4)	C22—N26—C27—C29	−178.7 (5)
N6—C7—C9—C10	−144.7 (4)	N26—C27—C29—C30	−89.3 (7)
N6—C7—C9—C11	93.5 (5)	N26—C27—C29—C31	146.0 (6)
O8—C7—C9—C10	36.6 (6)	O28—C27—C29—C30	89.1 (8)
O8—C7—C9—C11	−85.2 (6)	O28—C27—C29—C31	−35.6 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O28^i	0.82 (6)	2.10 (6)	2.911 (5)	168 (5)
N26—H26···O8	0.80 (7)	2.06 (7)	2.857 (5)	173 (6)

Symmetry code: (i) −x+1, −y+1, z−1/2.