2,2,2-Trimethyl-N-(3-methyl­phen­yl)­acetamide

The conformation of the N-H bond is anti to the meta-methyl substituent in the structure of the title compound, C₁₂H₁₇NO, in contrast to the ortho-methyl-substituted amide.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.041
• wR factor = 0.102
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       5.20 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.43 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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           26.00
           From the CIF: _reflns_number_total               1215
           Count of symmetry unique reflns         1222
           Completeness (_total/calc)             99.43%
           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
   0 ALERT level B = Potentially serious problem
   7 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
   2 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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED, (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) PLATON (Spek, 2003) WinGX (Farrugia, 1999).

N-(3-methylphenyl)-2,2,2-trimethylacetamide

Crystal data

C12H17NO	F(000) = 416
Mr = 191.27	Dx = 1.084 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2695 reflections
a = 10.753 (1) Å	θ = 2.7–30.0°
b = 10.8059 (10) Å	µ = 0.07 mm^−1
c = 10.0883 (11) Å	T = 299 K
V = 1172.2 (2) Å^3	Prism, colourless
Z = 4	0.5 × 0.15 × 0.15 mm

Data collection

Xcalibur System, Oxford Diffraction, Ltd. diffractometer	1215 independent reflections
Graphite monochromator	765 reflections with I > 2σ(I)
Detector resolution: 8.4012 pixels mm^-1	Rint = 0.075
ω scan	θmax = 26°, θmin = 4.2°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	h = −13→13
Tmin = 0.962, Tmax = 0.992	k = −13→13
7344 measured reflections	l = −12→7

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 0.88	w = 1/[σ^2(Fo^2) + (0.0648P)^2] where P = (Fo^2 + 2Fc^2)/3
1271 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.11 e Å^−3
1 restraint	Δρmin = −0.12 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	0.0278 (2)	0.1979 (3)	0.0617 (4)	0.0995 (11)
H11	−0.0478	0.1530	0.0777	0.149*
H12	0.0096	0.2710	0.0111	0.149*
H13	0.0645	0.2211	0.1448	0.149*
C2	0.1555 (3)	0.0049 (3)	0.0700 (4)	0.0930 (9)
H21	0.0848	−0.0483	0.0817	0.139*
H22	0.1839	0.0333	0.1549	0.139*
H23	0.2210	−0.0401	0.0269	0.139*
C3	0.0573 (3)	0.0747 (4)	−0.1428 (3)	0.1009 (12)
H31	−0.0178	0.0305	−0.1225	0.151*
H32	0.1129	0.0216	−0.1906	0.151*
H33	0.0377	0.1458	−0.1960	0.151*
C4	0.1184 (2)	0.1162 (3)	−0.0155 (2)	0.0637 (7)
C5	0.2357 (2)	0.1914 (2)	−0.0479 (3)	0.0545 (6)
C8	0.4116 (2)	0.3049 (2)	0.0536 (3)	0.0538 (6)
C9	0.4995 (2)	0.2904 (2)	−0.0432 (3)	0.0669 (7)
H16A	0.4856	0.2343	−0.1115	0.080*
C10	0.6090 (3)	0.3583 (3)	−0.0410 (4)	0.0860 (10)
C11	0.6240 (4)	0.4435 (4)	0.0598 (5)	0.1097 (14)
H14A	0.6952	0.4924	0.0616	0.132*
C12	0.5365 (4)	0.4576 (3)	0.1570 (5)	0.1045 (13)
H13A	0.5494	0.5144	0.2249	0.125*
C13	0.4302 (3)	0.3883 (3)	0.1547 (3)	0.0750 (9)
H12A	0.3708	0.3975	0.2210	0.090*
C14	0.7062 (3)	0.3377 (6)	−0.1442 (5)	0.1393 (17)
H141	0.7672	0.4024	−0.1391	0.209*
H142	0.6683	0.3382	−0.2304	0.209*
H143	0.7456	0.2592	−0.1294	0.209*
N7	0.30059 (18)	0.23368 (18)	0.0564 (2)	0.0574 (6)
H7	0.2717	0.2156	0.1335	0.069*
O6	0.26821 (17)	0.21176 (19)	−0.16102 (18)	0.0791 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0604 (17)	0.137 (3)	0.101 (2)	−0.0147 (18)	0.0071 (19)	−0.018 (3)
C2	0.105 (2)	0.0873 (18)	0.086 (2)	−0.0325 (18)	−0.001 (2)	0.012 (2)
C3	0.099 (2)	0.140 (3)	0.0636 (18)	−0.062 (2)	−0.0054 (17)	−0.014 (2)
C4	0.0614 (14)	0.0847 (17)	0.0451 (14)	−0.0223 (14)	0.0006 (14)	−0.0025 (14)
C5	0.0564 (14)	0.0726 (14)	0.0343 (12)	−0.0075 (13)	−0.0037 (13)	−0.0027 (15)
C8	0.0539 (13)	0.0555 (12)	0.0520 (14)	−0.0048 (11)	−0.0147 (14)	0.0079 (14)
C9	0.0574 (14)	0.0784 (16)	0.0648 (16)	−0.0099 (14)	−0.0070 (15)	0.0179 (17)
C10	0.0577 (17)	0.103 (2)	0.097 (2)	−0.0157 (17)	−0.021 (2)	0.046 (2)
C11	0.078 (2)	0.095 (2)	0.156 (4)	−0.037 (2)	−0.056 (3)	0.033 (3)
C12	0.105 (3)	0.085 (2)	0.123 (3)	−0.011 (2)	−0.052 (3)	−0.014 (2)
C13	0.0698 (18)	0.0705 (17)	0.085 (2)	0.0010 (15)	−0.0323 (17)	−0.0105 (17)
C14	0.0622 (19)	0.211 (4)	0.145 (4)	−0.015 (2)	0.012 (3)	0.067 (4)
N7	0.0600 (11)	0.0777 (13)	0.0347 (11)	−0.0171 (10)	−0.0008 (10)	−0.0040 (11)
O6	0.0694 (12)	0.1308 (17)	0.0371 (11)	−0.0288 (12)	0.0009 (10)	−0.0006 (11)

Geometric parameters (Å, º)

C1—C4	1.529 (4)	C8—C13	1.376 (4)
C1—H11	0.9600	C8—N7	1.421 (3)
C1—H12	0.9600	C9—C10	1.387 (3)
C1—H13	0.9600	C9—H16A	0.9300
C2—C4	1.533 (4)	C10—C11	1.382 (6)
C2—H21	0.9600	C10—C14	1.492 (5)
C2—H22	0.9600	C11—C12	1.367 (6)
C2—H23	0.9600	C11—H14A	0.9300
C3—C4	1.510 (4)	C12—C13	1.367 (5)
C3—H31	0.9600	C12—H13A	0.9300
C3—H32	0.9600	C13—H12A	0.9300
C3—H33	0.9600	C14—H141	0.9600
C4—C5	1.535 (3)	C14—H142	0.9600
C5—O6	1.214 (3)	C14—H143	0.9600
C5—N7	1.343 (3)	N7—H7	0.8600
C8—C9	1.368 (4)
C4—C1—H11	109.5	C9—C8—C13	120.3 (2)
C4—C1—H12	109.5	C9—C8—N7	122.2 (2)
H11—C1—H12	109.5	C13—C8—N7	117.5 (2)
C4—C1—H13	109.5	C8—C9—C10	120.9 (3)
H11—C1—H13	109.5	C8—C9—H16A	119.5
H12—C1—H13	109.5	C10—C9—H16A	119.5
C4—C2—H21	109.5	C11—C10—C9	117.6 (4)
C4—C2—H22	109.5	C11—C10—C14	122.1 (4)
H21—C2—H22	109.5	C9—C10—C14	120.3 (4)
C4—C2—H23	109.5	C12—C11—C10	121.4 (3)
H21—C2—H23	109.5	C12—C11—H14A	119.3
H22—C2—H23	109.5	C10—C11—H14A	119.3
C4—C3—H31	109.5	C13—C12—C11	120.1 (3)
C4—C3—H32	109.5	C13—C12—H13A	119.9
H31—C3—H32	109.5	C11—C12—H13A	119.9
C4—C3—H33	109.5	C12—C13—C8	119.6 (3)
H31—C3—H33	109.5	C12—C13—H12A	120.2
H32—C3—H33	109.5	C8—C13—H12A	120.2
C3—C4—C1	109.1 (3)	C10—C14—H141	109.5
C3—C4—C2	111.0 (3)	C10—C14—H142	109.5
C1—C4—C2	109.4 (3)	H141—C14—H142	109.5
C3—C4—C5	109.5 (2)	C10—C14—H143	109.5
C1—C4—C5	109.1 (2)	H141—C14—H143	109.5
C2—C4—C5	108.8 (2)	H142—C14—H143	109.5
O6—C5—N7	121.7 (2)	C5—N7—C8	127.2 (2)
O6—C5—C4	122.2 (2)	C5—N7—H7	116.4
N7—C5—C4	116.1 (2)	C8—N7—H7	116.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O6^i	0.86	2.12	2.954 (3)	164

Symmetry code: (i) −x+1/2, y, z+1/2.