N-(3,5-Dichloro­phen­yl)-2,2,2-trimethyl­acetamide

Mol­ecules of the title compound, C₁₁H₁₃Cl₂NO, are linked into a chain running along the b-axis direction. The structure shows a close resemblance to those of related amides but with slightly different bond parameters.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.094
• wR factor = 0.206
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
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        C12
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   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
   0 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, 2006); 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); PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

N-(3,5-dichlorophenyl)-2,2,2-trimethylacetamide

Crystal data

C11H13Cl2NO	F(000) = 1024
Mr = 246.12	Dx = 1.319 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2400 reflections
a = 10.655 (2) Å	θ = 2.9–20.7°
b = 9.999 (3) Å	µ = 0.50 mm^−1
c = 23.275 (9) Å	T = 299 K
V = 2479.7 (13) Å^3	Needle, colourless
Z = 8	0.40 × 0.14 × 0.03 mm

Data collection

Xcalibur System, Oxford Diffraction, Ltd. diffractometer	2250 independent reflections
Graphite monochromator	1165 reflections with I > 2σ(I)
Detector resolution: 8.4012 pixels mm^-1	Rint = 0.078
ω scan	θmax = 25.3°, θmin = 4.1°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	h = −12→12
Tmin = 0.855, Tmax = 0.976	k = −7→12
14622 measured reflections	l = −28→28

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)] = 0.094	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.206	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.076P)^2] where P = (Fo^2 + 2Fc^2)/3
2250 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.19 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	0.1500 (6)	0.0776 (6)	0.2488 (3)	0.0999 (19)
H1A	0.2089	0.0275	0.2714	0.12*
H1B	0.077	0.0971	0.2715	0.12*
H1C	0.1882	0.1597	0.2365	0.12*
C2	0.0519 (7)	−0.1317 (6)	0.2155 (3)	0.106 (2)
H2A	0.0399	−0.1897	0.1831	0.127*
H2B	−0.0278	−0.1124	0.2328	0.127*
H2C	0.1052	−0.1749	0.2431	0.127*
C3	0.0189 (5)	0.0759 (7)	0.1616 (3)	0.105 (2)
H3A	0.0565	0.1592	0.1505	0.126*
H3B	−0.0544	0.0931	0.1844	0.126*
H3C	−0.0046	0.0267	0.1278	0.126*
C4	0.1117 (5)	−0.0047 (5)	0.1961 (2)	0.0660 (14)
C5	0.2283 (5)	−0.0349 (5)	0.16122 (18)	0.0564 (12)
O6	0.2686 (3)	−0.1446 (3)	0.15364 (16)	0.0812 (12)
N7	0.2862 (4)	0.0737 (4)	0.13774 (17)	0.0669 (12)
H7	0.2507	0.1499	0.1431	0.08*
C8	0.3987 (5)	0.0742 (5)	0.1054 (2)	0.0582 (13)
C9	0.4925 (5)	−0.0181 (5)	0.1131 (2)	0.0606 (13)
H9	0.4819	−0.0883	0.1389	0.073*
C10	0.6006 (5)	−0.0062 (6)	0.0828 (2)	0.0753 (15)
C11	0.6187 (6)	0.0926 (7)	0.0432 (3)	0.0849 (18)
H11	0.6925	0.0975	0.022	0.102*
C12	0.5252 (6)	0.1838 (6)	0.0358 (2)	0.0747 (16)
C13	0.4139 (5)	0.1769 (5)	0.0658 (2)	0.0676 (14)
H13	0.3507	0.2395	0.0598	0.081*
Cl14	0.71894 (16)	−0.12088 (19)	0.09410 (9)	0.1217 (8)
Cl15	0.54236 (18)	0.3112 (2)	−0.01356 (7)	0.1213 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.113 (5)	0.096 (4)	0.091 (4)	0.003 (4)	0.032 (4)	−0.009 (4)
C2	0.123 (6)	0.067 (4)	0.128 (5)	−0.008 (4)	0.056 (4)	0.008 (4)
C3	0.070 (4)	0.125 (5)	0.121 (5)	0.014 (4)	0.015 (3)	0.037 (4)
C4	0.069 (3)	0.050 (3)	0.078 (3)	−0.001 (3)	0.016 (3)	0.001 (3)
C5	0.062 (3)	0.046 (3)	0.061 (3)	−0.002 (3)	0.003 (2)	0.000 (3)
O6	0.084 (3)	0.0403 (18)	0.120 (3)	0.004 (2)	0.026 (2)	−0.002 (2)
N7	0.070 (3)	0.044 (2)	0.087 (3)	0.007 (2)	0.024 (2)	0.008 (2)
C8	0.065 (3)	0.051 (3)	0.059 (3)	−0.009 (3)	0.006 (3)	−0.009 (3)
C9	0.059 (3)	0.051 (3)	0.072 (3)	−0.002 (3)	0.007 (3)	−0.008 (3)
C10	0.068 (4)	0.074 (4)	0.084 (4)	−0.014 (3)	0.006 (3)	−0.019 (3)
C11	0.077 (4)	0.098 (5)	0.080 (4)	−0.033 (4)	0.022 (3)	−0.025 (4)
C12	0.087 (4)	0.076 (4)	0.061 (3)	−0.026 (4)	0.006 (3)	−0.003 (3)
C13	0.076 (4)	0.060 (3)	0.066 (3)	−0.010 (3)	0.002 (3)	0.001 (3)
Cl14	0.0716 (11)	0.1218 (15)	0.1719 (19)	0.0203 (10)	0.0100 (10)	−0.0248 (12)
Cl15	0.1461 (16)	0.1320 (15)	0.0859 (11)	−0.0582 (13)	0.0058 (10)	0.0321 (10)

Geometric parameters (Å, º)

C1—C4	1.532 (7)	C5—N7	1.364 (5)
C1—H1A	0.96	N7—C8	1.415 (6)
C1—H1B	0.96	N7—H7	0.86
C1—H1C	0.96	C8—C9	1.372 (6)
C2—C4	1.491 (7)	C8—C13	1.389 (6)
C2—H2A	0.96	C9—C10	1.357 (7)
C2—H2B	0.96	C9—H9	0.93
C2—H2C	0.96	C10—C11	1.365 (8)
C3—C4	1.508 (7)	C10—Cl14	1.724 (6)
C3—H3A	0.96	C11—C12	1.361 (8)
C3—H3B	0.96	C11—H11	0.93
C3—H3C	0.96	C12—C13	1.379 (7)
C4—C5	1.515 (7)	C12—Cl15	1.725 (6)
C5—O6	1.191 (5)	C13—H13	0.93
C4—C1—H1A	109.5	O6—C5—N7	120.7 (4)
C4—C1—H1B	109.5	O6—C5—C4	124.0 (4)
H1A—C1—H1B	109.5	N7—C5—C4	115.3 (4)
C4—C1—H1C	109.5	C5—N7—C8	126.8 (4)
H1A—C1—H1C	109.5	C5—N7—H7	116.6
H1B—C1—H1C	109.5	C8—N7—H7	116.6
C4—C2—H2A	109.5	C9—C8—C13	120.0 (5)
C4—C2—H2B	109.5	C9—C8—N7	123.0 (5)
H2A—C2—H2B	109.5	C13—C8—N7	117.0 (5)
C4—C2—H2C	109.5	C10—C9—C8	119.4 (5)
H2A—C2—H2C	109.5	C10—C9—H9	120.3
H2B—C2—H2C	109.5	C8—C9—H9	120.3
C4—C3—H3A	109.5	C9—C10—C11	122.3 (6)
C4—C3—H3B	109.5	C9—C10—Cl14	118.9 (5)
H3A—C3—H3B	109.5	C11—C10—Cl14	118.8 (5)
C4—C3—H3C	109.5	C12—C11—C10	117.9 (5)
H3A—C3—H3C	109.5	C12—C11—H11	121.1
H3B—C3—H3C	109.5	C10—C11—H11	121.1
C2—C4—C3	109.7 (5)	C11—C12—C13	122.1 (5)
C2—C4—C5	110.1 (4)	C11—C12—Cl15	120.1 (5)
C3—C4—C5	111.0 (4)	C13—C12—Cl15	117.8 (5)
C2—C4—C1	109.2 (5)	C12—C13—C8	118.3 (5)
C3—C4—C1	108.3 (5)	C12—C13—H13	120.9
C5—C4—C1	108.5 (4)	C8—C13—H13	120.9
C2—C4—C5—O6	−3.9 (7)	N7—C8—C9—C10	−176.1 (4)
C3—C4—C5—O6	−125.5 (6)	C8—C9—C10—C11	−2.1 (8)
C1—C4—C5—O6	115.5 (5)	C8—C9—C10—Cl14	178.6 (4)
C2—C4—C5—N7	175.7 (5)	C9—C10—C11—C12	2.0 (8)
C3—C4—C5—N7	54.1 (6)	Cl14—C10—C11—C12	−178.7 (4)
C1—C4—C5—N7	−64.9 (6)	C10—C11—C12—C13	−1.4 (8)
O6—C5—N7—C8	−3.2 (8)	C10—C11—C12—Cl15	179.9 (4)
C4—C5—N7—C8	177.3 (4)	C11—C12—C13—C8	0.9 (8)
C5—N7—C8—C9	−29.3 (7)	Cl15—C12—C13—C8	179.6 (3)
C5—N7—C8—C13	153.0 (5)	C9—C8—C13—C12	−0.9 (7)
C13—C8—C9—C10	1.5 (7)	N7—C8—C13—C12	176.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O6^i	0.86	2.08	2.900 (5)	159

Symmetry code: (i) −x+1/2, y+1/2, z.