N-(3,5-Dimethyl­phen­yl)-2,2-dimethyl­propanamide

Gowda, B.T.; Kožíšek, J.; Tokarčík, M.; Fuess, H.

doi:10.1107/S1600536807012810

N-(3,5-Dimethylphenyl)-2,2-dimethylpropanamide

B. T. Gowda, J. Kožíšek, M. Tokarčík and H. Fuess

Molecules of the title compound, C₁₃H₁₉NO, are linked into a chain running along the b-axis direction by an N—H

O hydrogen bond [H

O = 2.09 Å, N

O = 2.924 (3)Å and N—H

O = 165°].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012810/ci2305sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012810/ci2305Isup2.hkl Contains datablock I

CCDC reference: 614910

checkCIF report

Key indicators

Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.005 Å
R factor = 0.053
wR factor = 0.166
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         37 Perc.

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C4      ..       5.46 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       6.03 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); 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); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

N-(3,5-Dimethylphenyl)-2,2-dimethylpropanamide top

Crystal data top

C₁₃H₁₉NO	F(000) = 896
M_r = 205.29	D_x = 1.059 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2737 reflections
a = 10.7076 (10) Å	θ = 2.5–27.4°
b = 10.044 (1) Å	µ = 0.07 mm⁻¹
c = 23.949 (2) Å	T = 299 K
V = 2575.7 (4) Å³	Prism, colourless
Z = 8	0.48 × 0.19 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2505 independent reflections
Graphite monochromator	936 reflections with I > 2σ(I)
Detector resolution: 8.4012 pixels mm^-1	R_int = 0.049
ω scans	θ_max = 26.4°, θ_min = 3.4°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	h = −13→13
T_min = 0.983, T_max = 0.996	k = −6→12
11204 measured reflections	l = −29→29

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ²(F_o²) + (0.0751P)²] where P = (F_o² + 2F_c²)/3
2505 reflections	(Δ/σ)_max < 0.001
153 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.14 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	U_iso*/U_eq	Occ. (<1)
C1	0.1569 (4)	1.0966 (4)	0.24756 (15)	0.0960 (12)
H1A	0.2199	1.0499	0.2683	0.115*
H1B	0.0853	1.111	0.2709	0.115*
H1C	0.1893	1.1809	0.2354	0.115*
C2	0.0585 (3)	0.8858 (3)	0.21523 (16)	0.0975 (13)
H2A	0.117	0.8349	0.2369	0.117*
H2B	0.0337	0.8355	0.183	0.117*
H2C	−0.0136	0.9054	0.2375	0.117*
C3	0.0261 (3)	1.0960 (4)	0.16289 (17)	0.1013 (13)
H3A	0.0635	1.1793	0.1527	0.122*
H3B	−0.0473	1.1123	0.1849	0.122*
H3C	0.0034	1.0477	0.1298	0.122*
C4	0.1190 (3)	1.0143 (3)	0.19686 (13)	0.0560 (8)
C5	0.2343 (3)	0.9849 (3)	0.16186 (12)	0.0507 (8)
O6	0.27083 (18)	0.87151 (19)	0.15331 (10)	0.0739 (7)
N7	0.2960 (2)	1.0908 (2)	0.14109 (10)	0.0564 (8)
H7	0.2657	1.1678	0.1489	0.068*
C8	0.4052 (3)	1.0892 (3)	0.10774 (12)	0.0500 (8)
C9	0.5001 (3)	0.9981 (3)	0.11618 (14)	0.0591 (9)
H9	0.488 (3)	0.933 (3)	0.1454 (11)	0.071*
C10	0.6075 (3)	1.0022 (3)	0.08385 (16)	0.0691 (10)
C11	0.6163 (4)	1.0984 (5)	0.04267 (16)	0.0771 (11)
H11	0.693 (3)	1.100 (3)	0.0173 (13)	0.093*
C12	0.5241 (4)	1.1903 (4)	0.03362 (13)	0.0688 (10)
C13	0.4187 (3)	1.1855 (3)	0.06645 (14)	0.0609 (9)
H13	0.349 (3)	1.250 (3)	0.0579 (12)	0.073*
C14	0.7102 (3)	0.9033 (4)	0.09416 (19)	0.1129 (15)
H14A	0.7896	0.9473	0.0917	0.135*	0.59 (4)
H14B	0.706	0.8339	0.0666	0.135*	0.59 (4)
H14C	0.7007	0.8654	0.1307	0.135*	0.59 (4)
H14D	0.6746	0.8171	0.101	0.135*	0.41 (4)
H14E	0.7582	0.9305	0.1261	0.135*	0.41 (4)
H14F	0.7635	0.899	0.062	0.135*	0.41 (4)
C15	0.5372 (3)	1.2914 (4)	−0.01194 (15)	0.1091 (14)
H15A	0.5202	1.3785	0.0027	0.131*	0.44 (4)
H15B	0.4791	1.2717	−0.0414	0.131*	0.44 (4)
H15C	0.6208	1.2889	−0.0264	0.131*	0.44 (4)
H15D	0.5599	1.2476	−0.0461	0.131*	0.56 (4)
H15E	0.6009	1.3544	−0.002	0.131*	0.56 (4)
H15F	0.4593	1.3372	−0.017	0.131*	0.56 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.108 (3)	0.101 (3)	0.079 (3)	−0.006 (2)	0.030 (2)	−0.013 (3)
C2	0.099 (3)	0.064 (2)	0.130 (3)	−0.010 (2)	0.052 (2)	0.010 (2)
C3	0.065 (2)	0.110 (3)	0.129 (3)	0.009 (2)	0.015 (2)	0.031 (3)
C4	0.060 (2)	0.0442 (17)	0.064 (2)	0.0018 (17)	0.0138 (18)	0.0039 (17)
C5	0.056 (2)	0.0365 (17)	0.0600 (19)	−0.0005 (17)	0.0012 (17)	−0.0014 (17)
O6	0.0713 (15)	0.0340 (11)	0.1164 (19)	0.0000 (11)	0.0239 (13)	−0.0024 (12)
N7	0.0622 (18)	0.0338 (14)	0.0732 (18)	0.0021 (13)	0.0220 (14)	−0.0012 (13)
C8	0.052 (2)	0.0418 (17)	0.056 (2)	−0.0038 (17)	0.0094 (17)	−0.0118 (17)
C9	0.059 (2)	0.051 (2)	0.067 (2)	−0.0044 (19)	0.005 (2)	−0.0128 (18)
C10	0.050 (2)	0.071 (2)	0.086 (3)	−0.008 (2)	0.010 (2)	−0.026 (2)
C11	0.068 (3)	0.092 (3)	0.071 (3)	−0.032 (3)	0.020 (2)	−0.021 (2)
C12	0.074 (3)	0.075 (3)	0.057 (2)	−0.029 (2)	0.005 (2)	−0.003 (2)
C13	0.067 (3)	0.057 (2)	0.059 (2)	−0.0133 (18)	0.001 (2)	0.005 (2)
C14	0.069 (3)	0.113 (3)	0.156 (4)	0.011 (3)	0.009 (2)	−0.025 (3)
C15	0.119 (3)	0.131 (3)	0.077 (3)	−0.048 (3)	0.011 (2)	0.019 (3)

Geometric parameters (Å, º) top

C1—C4	1.523 (4)	C9—H9	0.97 (3)
C1—H1A	0.96	C10—C11	1.385 (5)
C1—H1B	0.96	C10—C14	1.502 (4)
C1—H1C	0.96	C11—C12	1.369 (5)
C2—C4	1.509 (4)	C11—H11	1.02 (3)
C2—H2A	0.96	C12—C13	1.377 (4)
C2—H2B	0.96	C12—C15	1.498 (4)
C2—H2C	0.96	C13—H13	1.01 (3)
C3—C4	1.524 (4)	C14—H14A	0.96
C3—H3A	0.96	C14—H14B	0.96
C3—H3B	0.96	C14—H14C	0.96
C3—H3C	0.96	C14—H14D	0.96
C4—C5	1.522 (4)	C14—H14E	0.96
C5—O6	1.222 (3)	C14—H14F	0.96
C5—N7	1.347 (3)	C15—H15A	0.96
N7—C8	1.418 (3)	C15—H15B	0.96
N7—H7	0.86	C15—H15C	0.96
C8—C9	1.382 (4)	C15—H15D	0.96
C8—C13	1.391 (4)	C15—H15E	0.96
C9—C10	1.389 (4)	C15—H15F	0.96

C4—C1—H1A	109.5	C12—C13—C8	121.1 (3)
C4—C1—H1B	109.5	C12—C13—H13	117.7 (16)
H1A—C1—H1B	109.5	C8—C13—H13	121.1 (16)
C4—C1—H1C	109.5	C10—C14—H14A	109.5
H1A—C1—H1C	109.5	C10—C14—H14B	109.5
H1B—C1—H1C	109.5	H14A—C14—H14B	109.5
C4—C2—H2A	109.5	C10—C14—H14C	109.5
C4—C2—H2B	109.5	H14A—C14—H14C	109.5
H2A—C2—H2B	109.5	H14B—C14—H14C	109.5
C4—C2—H2C	109.5	C10—C14—H14D	109.5
H2A—C2—H2C	109.5	H14A—C14—H14D	141.1
H2B—C2—H2C	109.5	H14B—C14—H14D	56.3
C4—C3—H3A	109.5	H14C—C14—H14D	56.3
C4—C3—H3B	109.5	C10—C14—H14E	109.5
H3A—C3—H3B	109.5	H14A—C14—H14E	56.3
C4—C3—H3C	109.5	H14B—C14—H14E	141.1
H3A—C3—H3C	109.5	H14C—C14—H14E	56.3
H3B—C3—H3C	109.5	H14D—C14—H14E	109.5
C2—C4—C1	110.2 (3)	C10—C14—H14F	109.5
C2—C4—C5	110.1 (2)	H14A—C14—H14F	56.3
C1—C4—C5	109.2 (3)	H14B—C14—H14F	56.3
C2—C4—C3	109.6 (3)	H14C—C14—H14F	141.1
C1—C4—C3	107.8 (3)	H14D—C14—H14F	109.5
C5—C4—C3	109.9 (3)	H14E—C14—H14F	109.5
O6—C5—N7	121.1 (3)	C12—C15—H15A	109.5
O6—C5—C4	122.2 (3)	C12—C15—H15B	109.5
N7—C5—C4	116.7 (2)	H15A—C15—H15B	109.5
C5—N7—C8	127.2 (2)	C12—C15—H15C	109.5
C5—N7—H7	116.4	H15A—C15—H15C	109.5
C8—N7—H7	116.4	H15B—C15—H15C	109.5
C9—C8—C13	119.2 (3)	C12—C15—H15D	109.5
C9—C8—N7	122.1 (3)	H15A—C15—H15D	141.1
C13—C8—N7	118.7 (3)	H15B—C15—H15D	56.3
C8—C9—C10	120.5 (3)	H15C—C15—H15D	56.3
C8—C9—H9	117.0 (18)	C12—C15—H15E	109.5
C10—C9—H9	122.4 (18)	H15A—C15—H15E	56.3
C11—C10—C9	118.4 (4)	H15B—C15—H15E	141.1
C11—C10—C14	121.9 (4)	H15C—C15—H15E	56.3
C9—C10—C14	119.7 (4)	H15D—C15—H15E	109.5
C12—C11—C10	122.3 (3)	C12—C15—H15F	109.5
C12—C11—H11	118.2 (18)	H15A—C15—H15F	56.3
C10—C11—H11	119.5 (18)	H15B—C15—H15F	56.3
C11—C12—C13	118.5 (3)	H15C—C15—H15F	141.1
C11—C12—C15	120.3 (4)	H15D—C15—H15F	109.5
C13—C12—C15	121.2 (4)	H15E—C15—H15F	109.5

C2—C4—C5—O6	−2.8 (4)	N7—C8—C9—C10	−177.9 (3)
C1—C4—C5—O6	118.3 (3)	C8—C9—C10—C11	−0.8 (4)
C3—C4—C5—O6	−123.6 (3)	C8—C9—C10—C14	179.3 (3)
C2—C4—C5—N7	178.1 (3)	C9—C10—C11—C12	1.2 (5)
C1—C4—C5—N7	−60.8 (3)	C14—C10—C11—C12	−178.9 (3)
C3—C4—C5—N7	57.2 (4)	C10—C11—C12—C13	−0.6 (5)
O6—C5—N7—C8	0.6 (5)	C10—C11—C12—C15	−179.2 (3)
C4—C5—N7—C8	179.7 (3)	C11—C12—C13—C8	−0.4 (4)
C5—N7—C8—C9	−37.1 (4)	C15—C12—C13—C8	178.2 (3)
C5—N7—C8—C13	145.1 (3)	C9—C8—C13—C12	0.7 (4)
C13—C8—C9—C10	−0.1 (4)	N7—C8—C13—C12	178.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O6ⁱ	0.86	2.09	2.924 (3)	165

Symmetry code: (i) −x+1/2, y+1/2, z.

Table 1 Comparison of bond lengths (Å) and angles (°) of (I) with the corresponding values in the related compounds (II), (III), (IV) and (V) top

Parameter	(I)	(II)	(III)	(IV)	(V)
Space group	Pbca	Pbca	Pca2₁	P2₁c	Pbca
Z	8	8	4	4	8
C(r)—C(r)—mean	1.381	1.387	1.377	1.383	1.379
C(r)—C(r)—min	1.363	1.366	1.362	1.373	1.368
C(r)—C(r)—max	1.393	1.413	1.384	1.390	1.395
C(r)—N	1.417	1.426	1.420	1.424	1.402
N—C(O)	1.342	1.330	1.348	1.337	1.337
C—O	1.223	1.226	1.219	1.211	1.204
C(O)—C(side)	1.523	1.476	1.532	1.564	1.549
C(2r)—C(1r)—C(6r)	199.6	121.2	119.7	119.9	120.5
C(2r)—C(1r)—N	122.1	122.7	122.4	122.1	122.3
C(6r)—C(1r)—N	118.2	115.7	117.9	117.9	117.2
C(1r)—N—C(O)	127.2	129.3	126.8	125.4	126.4
N—C(O)—C(side)	116.8	117.7	116.1	114.8	113.8
N—C(O)—O	120.9	121.7	122.1	126.3	126.0
O—C(O)—C(side)	122.2	120.4	121.9	118.9	120.2

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N-(3,5-Dimethyl­phen­yl)-2,2-dimethyl­propanamide

Supporting information

Key indicators

checkCIF/PLATON results

N-(3,5-Dimethylphenyl)-2,2-dimethylpropanamide