In the structure of the title compound, C12H17NO, the conformation of the N-H bond is syn to the ortho-methyl substituent, in contrast to the anti conformation observed for the corresponding meta-methyl-substituted amide and side-chain-unsubstituted N-(2-methylphenyl)acetamide.
Supporting information
CCDC reference: 614912
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.007 Å
- R factor = 0.079
- wR factor = 0.222
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C4
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 26.54
From the CIF: _reflns_number_total 1375
Count of symmetry unique reflns 1381
Completeness (_total/calc) 99.57%
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
2 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
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrysAlis (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; 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); PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997)
PLATON (Spek, 2003)
WinGX (Farrugia, 1999).
N-(2-methylphenyl)-2,2,2-trimethylacetamide
top
Crystal data top
C12H17NO | F(000) = 416 |
Mr = 191.27 | Dx = 1.107 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | θ = 2.7–29.6° |
a = 10.138 (2) Å | µ = 0.07 mm−1 |
b = 10.2597 (19) Å | T = 299 K |
c = 11.0305 (19) Å | Prism, colourless |
V = 1147.3 (4) Å3 | 0.37 × 0.20 × 0.07 mm |
Z = 4 | |
Data collection top
Xcalibur System, Oxford Diffraction, Ltd. diffractometer | 1375 independent reflections |
Radiation source: fine-focus sealed tube | 1289 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
Detector resolution: 8.4012 pixels mm-1 | θmax = 26.5°, θmin = 4.2° |
ω scan | h = −12→7 |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) | k = −12→12 |
Tmin = 0.965, Tmax = 0.990 | l = −13→13 |
7986 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.222 | H-atom parameters constrained |
S = 1.1 | w = 1/[σ2(Fo2) + (0.1365P)2 + 0.2494P] where P = (Fo2 + 2Fc2)/3 |
1375 reflections | (Δ/σ)max = 0.001 |
137 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1829 (6) | 0.5077 (5) | 0.4741 (6) | 0.1002 (19) | |
H1A | 0.1236 | 0.5325 | 0.4103 | 0.12* | |
H1B | 0.2507 | 0.4524 | 0.4418 | 0.12* | |
H1C | 0.2222 | 0.5843 | 0.5086 | 0.12* | |
C2 | 0.1996 (9) | 0.4080 (6) | 0.6737 (7) | 0.135 (3) | |
H2A | 0.2694 | 0.3526 | 0.6453 | 0.162* | |
H2B | 0.1541 | 0.3659 | 0.7393 | 0.162* | |
H2C | 0.236 | 0.489 | 0.7016 | 0.162* | |
C3 | −0.0062 (5) | 0.5178 (5) | 0.6082 (7) | 0.100 (2) | |
H3A | −0.0727 | 0.5144 | 0.5463 | 0.12* | |
H3B | 0.0241 | 0.6059 | 0.6174 | 0.12* | |
H3C | −0.0427 | 0.4878 | 0.6835 | 0.12* | |
C4 | 0.1058 (3) | 0.4334 (4) | 0.5733 (4) | 0.0542 (9) | |
C5 | 0.0572 (3) | 0.3035 (3) | 0.5207 (3) | 0.0472 (8) | |
O6 | −0.0575 (2) | 0.2719 (3) | 0.5252 (3) | 0.0686 (9) | |
N7 | 0.1489 (3) | 0.2275 (3) | 0.4702 (3) | 0.0534 (8) | |
H7 | 0.2287 | 0.2558 | 0.4694 | 0.059 (11)* | |
C8 | 0.1245 (3) | 0.1033 (3) | 0.4176 (4) | 0.0494 (8) | |
C9 | 0.0657 (4) | 0.0068 (4) | 0.4825 (5) | 0.0639 (10) | |
H9 | 0.0384 | 0.0228 | 0.5616 | 0.077* | |
C10 | 0.0458 (5) | −0.1155 (4) | 0.4318 (5) | 0.0769 (13) | |
H10 | 0.0057 | −0.1815 | 0.4762 | 0.092* | |
C11 | 0.0866 (5) | −0.1369 (5) | 0.3149 (6) | 0.0830 (15) | |
H11 | 0.0741 | −0.2183 | 0.2797 | 0.1* | |
C12 | 0.1453 (4) | −0.0401 (5) | 0.2496 (4) | 0.0714 (12) | |
H12 | 0.1726 | −0.057 | 0.1707 | 0.086* | |
C13 | 0.1649 (3) | 0.0822 (4) | 0.2979 (3) | 0.0527 (9) | |
C14 | 0.2293 (5) | 0.1887 (5) | 0.2260 (4) | 0.0755 (12) | |
H14A | 0.2324 | 0.1643 | 0.1421 | 0.091* | |
H14B | 0.3173 | 0.2025 | 0.2554 | 0.091* | |
H14C | 0.1793 | 0.2677 | 0.2347 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.120 (4) | 0.069 (3) | 0.111 (4) | −0.031 (3) | 0.034 (4) | −0.008 (3) |
C2 | 0.213 (8) | 0.082 (4) | 0.110 (5) | 0.014 (5) | −0.089 (5) | −0.021 (3) |
C3 | 0.083 (3) | 0.060 (3) | 0.158 (6) | −0.006 (2) | 0.031 (4) | −0.038 (3) |
C4 | 0.0535 (18) | 0.0496 (18) | 0.0594 (19) | −0.0026 (15) | 0.0009 (15) | −0.0117 (17) |
C5 | 0.0473 (16) | 0.0488 (16) | 0.0455 (15) | −0.0001 (14) | −0.0017 (15) | −0.0025 (15) |
O6 | 0.0444 (13) | 0.0638 (16) | 0.098 (2) | −0.0027 (12) | 0.0039 (14) | −0.0235 (16) |
N7 | 0.0419 (14) | 0.0493 (16) | 0.0691 (18) | −0.0026 (12) | 0.0052 (14) | −0.0131 (14) |
C8 | 0.0427 (15) | 0.0430 (16) | 0.063 (2) | 0.0035 (13) | −0.0070 (15) | −0.0041 (16) |
C9 | 0.061 (2) | 0.052 (2) | 0.078 (3) | −0.0026 (18) | 0.001 (2) | −0.0016 (19) |
C10 | 0.071 (2) | 0.048 (2) | 0.111 (4) | −0.0074 (19) | −0.001 (3) | 0.005 (2) |
C11 | 0.071 (3) | 0.062 (3) | 0.116 (4) | 0.001 (2) | −0.009 (3) | −0.032 (3) |
C12 | 0.061 (2) | 0.075 (3) | 0.078 (3) | 0.005 (2) | −0.005 (2) | −0.026 (2) |
C13 | 0.0463 (17) | 0.056 (2) | 0.0562 (19) | 0.0069 (15) | −0.0051 (15) | −0.0044 (16) |
C14 | 0.076 (2) | 0.087 (3) | 0.063 (2) | 0.012 (2) | 0.009 (2) | 0.012 (2) |
Geometric parameters (Å, º) top
C1—C4 | 1.546 (7) | N7—H7 | 0.86 |
C1—H1A | 0.96 | C8—C9 | 1.360 (6) |
C1—H1B | 0.96 | C8—C13 | 1.400 (5) |
C1—H1C | 0.96 | C9—C10 | 1.387 (6) |
C2—C4 | 1.483 (7) | C9—H9 | 0.93 |
C2—H2A | 0.96 | C10—C11 | 1.373 (8) |
C2—H2B | 0.96 | C10—H10 | 0.93 |
C2—H2C | 0.96 | C11—C12 | 1.363 (7) |
C3—C4 | 1.479 (6) | C11—H11 | 0.93 |
C3—H3A | 0.96 | C12—C13 | 1.377 (6) |
C3—H3B | 0.96 | C12—H12 | 0.93 |
C3—H3C | 0.96 | C13—C14 | 1.500 (6) |
C4—C5 | 1.535 (5) | C14—H14A | 0.96 |
C5—O6 | 1.207 (4) | C14—H14B | 0.96 |
C5—N7 | 1.335 (4) | C14—H14C | 0.96 |
N7—C8 | 1.421 (4) | | |
| | | |
C4—C1—H1A | 109.5 | C5—N7—C8 | 124.9 (3) |
C4—C1—H1B | 109.5 | C5—N7—H7 | 117.5 |
H1A—C1—H1B | 109.5 | C8—N7—H7 | 117.5 |
C4—C1—H1C | 109.5 | C9—C8—C13 | 120.8 (4) |
H1A—C1—H1C | 109.5 | C9—C8—N7 | 121.0 (4) |
H1B—C1—H1C | 109.5 | C13—C8—N7 | 118.2 (3) |
C4—C2—H2A | 109.5 | C8—C9—C10 | 120.7 (5) |
C4—C2—H2B | 109.5 | C8—C9—H9 | 119.7 |
H2A—C2—H2B | 109.5 | C10—C9—H9 | 119.7 |
C4—C2—H2C | 109.5 | C11—C10—C9 | 118.7 (5) |
H2A—C2—H2C | 109.5 | C11—C10—H10 | 120.7 |
H2B—C2—H2C | 109.5 | C9—C10—H10 | 120.7 |
C4—C3—H3A | 109.5 | C12—C11—C10 | 120.7 (4) |
C4—C3—H3B | 109.5 | C12—C11—H11 | 119.6 |
H3A—C3—H3B | 109.5 | C10—C11—H11 | 119.6 |
C4—C3—H3C | 109.5 | C11—C12—C13 | 121.5 (4) |
H3A—C3—H3C | 109.5 | C11—C12—H12 | 119.2 |
H3B—C3—H3C | 109.5 | C13—C12—H12 | 119.2 |
C3—C4—C2 | 113.6 (5) | C12—C13—C8 | 117.6 (4) |
C3—C4—C5 | 111.1 (3) | C12—C13—C14 | 121.5 (4) |
C2—C4—C5 | 109.6 (4) | C8—C13—C14 | 120.9 (4) |
C3—C4—C1 | 106.4 (4) | C13—C14—H14A | 109.5 |
C2—C4—C1 | 106.9 (5) | C13—C14—H14B | 109.5 |
C5—C4—C1 | 108.8 (3) | H14A—C14—H14B | 109.5 |
O6—C5—N7 | 122.1 (3) | C13—C14—H14C | 109.5 |
O6—C5—C4 | 121.7 (3) | H14A—C14—H14C | 109.5 |
N7—C5—C4 | 116.2 (3) | H14B—C14—H14C | 109.5 |
| | | |
C3—C4—C5—O6 | −9.5 (6) | N7—C8—C9—C10 | −178.0 (4) |
C2—C4—C5—O6 | 117.0 (5) | C8—C9—C10—C11 | −0.1 (7) |
C1—C4—C5—O6 | −126.4 (5) | C9—C10—C11—C12 | −0.1 (7) |
C3—C4—C5—N7 | 170.7 (4) | C10—C11—C12—C13 | −0.4 (7) |
C2—C4—C5—N7 | −62.9 (6) | C11—C12—C13—C8 | 1.1 (6) |
C1—C4—C5—N7 | 53.8 (5) | C11—C12—C13—C14 | −179.9 (4) |
O6—C5—N7—C8 | −0.5 (6) | C9—C8—C13—C12 | −1.3 (5) |
C4—C5—N7—C8 | 179.4 (4) | N7—C8—C13—C12 | 177.6 (3) |
C5—N7—C8—C9 | −55.9 (5) | C9—C8—C13—C14 | 179.7 (4) |
C5—N7—C8—C13 | 125.3 (4) | N7—C8—C13—C14 | −1.4 (5) |
C13—C8—C9—C10 | 0.8 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7···O6i | 0.86 | 2.19 | 2.977 (4) | 153 |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |