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

In the structure of the title compound (3CPTMA), C₁₁H₁₄ClNO, the conformation of the N—H bond is anti to the meta-chloro substituent, similar to that observed for the corresponding meta-methyl-substituted amide. The bond parameters of the two amides are also similar. The mol­ecules in 3CPTMA are linked into chains, as bent columns, through N—H...O hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.015 Å
• R factor = 0.071
• wR factor = 0.153
• Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level B
RINTA01_ALERT_3_B  The value of Rint is greater than 0.15
            Rint given   0.152
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 .........       0.15
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         15

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.08
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C11 H14 Cl N O

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      1.080
            Tmax scaled      0.923 Tmin scaled      0.814
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           66.89
           From the CIF: _reflns_number_total               1095
           Count of symmetry unique reflns         1094
           Completeness (_total/calc)            100.09%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   2 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
   6 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4-PC (Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia 1997); software used to prepare material for publication: SHELXL97.

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

Crystal data

C11H14ClNO	F(000) = 448
Mr = 211.68	Dx = 1.214 Mg m^−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 10.778 (1) Å	θ = 8.3–21.7°
b = 10.623 (1) Å	µ = 2.66 mm^−1
c = 10.117 (2) Å	T = 299 K
V = 1158.3 (3) Å^3	Needle, colourless
Z = 4	0.68 × 0.05 × 0.03 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	479 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.152
Graphite monochromator	θmax = 66.9°, θmin = 4.2°
ω/2θ scans	h = −12→6
Absorption correction: ψ scan (North et al., 1968)	k = −12→0
Tmin = 0.754, Tmax = 0.855	l = 0→12
1745 measured reflections	3 standard reflections every 120 min
1095 independent reflections	intensity decay: 50%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.071	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0368P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.003
1095 reflections	Δρmax = 0.23 e Å^−3
127 parameters	Δρmin = −0.28 e Å^−3
1 restraint	Absolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (7)

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	−0.4773 (10)	0.6997 (10)	−0.1593 (13)	0.085 (4)
H1A	−0.5514	0.6519	−0.1756	0.102*
H1B	−0.4427	0.7270	−0.2419	0.102*
H1C	−0.4971	0.7717	−0.1061	0.102*
C2	−0.3486 (10)	0.5007 (10)	−0.1692 (11)	0.090 (4)
H2A	−0.3124	0.5270	−0.2514	0.108*
H2B	−0.4220	0.4521	−0.1864	0.108*
H2C	−0.2900	0.4503	−0.1212	0.108*
C3	−0.4450 (11)	0.5723 (9)	0.0420 (9)	0.084 (4)
H3A	−0.5190	0.5262	0.0211	0.101*
H3B	−0.4659	0.6438	0.0956	0.101*
H3C	−0.3887	0.5189	0.0895	0.101*
C4	−0.3830 (8)	0.6174 (10)	−0.0867 (8)	0.053 (3)
C5	−0.2673 (10)	0.6910 (8)	−0.0546 (9)	0.055 (3)
C8	−0.0913 (9)	0.8055 (8)	−0.1558 (9)	0.042 (2)
C9	−0.0044 (10)	0.7876 (9)	−0.0566 (10)	0.051 (2)
H9	−0.0189	0.7313	0.0121	0.062*
C10	0.1051 (9)	0.8563 (10)	−0.0627 (12)	0.070 (3)
C11	0.1299 (10)	0.9394 (11)	−0.1635 (14)	0.082 (4)
H11	0.2050	0.9824	−0.1668	0.099*
C12	0.0423 (11)	0.9571 (11)	−0.2580 (15)	0.086 (4)
H12	0.0562	1.0157	−0.3246	0.103*
C13	−0.0677 (9)	0.8893 (9)	−0.2571 (11)	0.059 (3)
H13	−0.1254	0.9002	−0.3245	0.071*
N7	−0.2034 (7)	0.7372 (7)	−0.1591 (6)	0.049 (2)
H7N	−0.2347	0.7234	−0.2360	0.059*
O6	−0.2354 (6)	0.7141 (6)	0.0592 (6)	0.0651 (19)
Cl14	0.2152 (3)	0.8302 (3)	0.0598 (4)	0.1163 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.056 (6)	0.111 (9)	0.087 (8)	−0.012 (8)	−0.005 (7)	0.027 (10)
C2	0.113 (10)	0.093 (7)	0.064 (7)	−0.024 (10)	0.001 (9)	0.002 (8)
C3	0.097 (8)	0.107 (8)	0.050 (6)	−0.042 (8)	0.018 (7)	0.016 (7)
C4	0.056 (6)	0.075 (7)	0.028 (5)	−0.020 (6)	−0.003 (5)	0.013 (5)
C5	0.060 (6)	0.067 (7)	0.038 (5)	−0.010 (6)	−0.001 (5)	−0.009 (6)
C8	0.055 (5)	0.035 (5)	0.036 (5)	0.001 (5)	0.013 (5)	−0.007 (5)
C9	0.055 (5)	0.054 (6)	0.045 (5)	−0.015 (5)	0.009 (5)	−0.008 (6)
C10	0.064 (7)	0.071 (8)	0.075 (8)	−0.004 (7)	0.017 (7)	−0.029 (7)
C11	0.051 (7)	0.070 (8)	0.125 (12)	−0.005 (6)	0.033 (9)	−0.002 (11)
C12	0.080 (8)	0.070 (9)	0.108 (11)	0.009 (9)	0.028 (9)	0.014 (9)
C13	0.062 (7)	0.059 (7)	0.056 (7)	0.003 (6)	0.013 (6)	0.002 (6)
N7	0.063 (5)	0.068 (5)	0.015 (3)	−0.020 (4)	0.003 (4)	0.001 (4)
O6	0.064 (4)	0.110 (5)	0.021 (3)	−0.027 (4)	−0.001 (4)	0.000 (5)
Cl14	0.0589 (14)	0.189 (3)	0.100 (2)	−0.014 (2)	−0.018 (2)	−0.043 (3)

Geometric parameters (Å, º)

C1—C4	1.529 (13)	C5—N7	1.354 (11)
C1—H1A	0.9600	C8—C13	1.381 (12)
C1—H1B	0.9600	C8—C9	1.386 (13)
C1—H1C	0.9600	C8—N7	1.409 (12)
C2—C4	1.540 (13)	C9—C10	1.389 (14)
C2—H2A	0.9600	C9—H9	0.9300
C2—H2B	0.9600	C10—C11	1.375 (15)
C2—H2C	0.9600	C10—Cl14	1.737 (12)
C3—C4	1.539 (12)	C11—C12	1.357 (18)
C3—H3A	0.9600	C11—H11	0.9300
C3—H3B	0.9600	C12—C13	1.387 (15)
C3—H3C	0.9600	C12—H12	0.9300
C4—C5	1.507 (14)	C13—H13	0.9300
C5—O6	1.227 (10)	N7—H7N	0.8600
C4—C1—H1A	109.5	O6—C5—N7	121.2 (9)
C4—C1—H1B	109.5	O6—C5—C4	122.5 (9)
H1A—C1—H1B	109.5	N7—C5—C4	116.2 (7)
C4—C1—H1C	109.5	C13—C8—C9	120.1 (9)
H1A—C1—H1C	109.5	C13—C8—N7	118.2 (9)
H1B—C1—H1C	109.5	C9—C8—N7	121.7 (8)
C4—C2—H2A	109.5	C8—C9—C10	118.0 (10)
C4—C2—H2B	109.5	C8—C9—H9	121.0
H2A—C2—H2B	109.5	C10—C9—H9	121.0
C4—C2—H2C	109.5	C11—C10—C9	122.4 (12)
H2A—C2—H2C	109.5	C11—C10—Cl14	119.9 (9)
H2B—C2—H2C	109.5	C9—C10—Cl14	117.7 (10)
C4—C3—H3A	109.5	C12—C11—C10	118.4 (12)
C4—C3—H3B	109.5	C12—C11—H11	120.8
H3A—C3—H3B	109.5	C10—C11—H11	120.8
C4—C3—H3C	109.5	C11—C12—C13	121.2 (13)
H3A—C3—H3C	109.5	C11—C12—H12	119.4
H3B—C3—H3C	109.5	C13—C12—H12	119.4
C5—C4—C1	110.9 (8)	C8—C13—C12	119.8 (11)
C5—C4—C3	109.8 (8)	C8—C13—H13	120.1
C1—C4—C3	107.2 (9)	C12—C13—H13	120.1
C5—C4—C2	109.6 (8)	C5—N7—C8	127.2 (7)
C1—C4—C2	111.1 (8)	C5—N7—H7N	116.4
C3—C4—C2	108.2 (8)	C8—N7—H7N	116.4
C1—C4—C5—O6	114.9 (11)	C9—C10—C11—C12	2.0 (17)
C3—C4—C5—O6	−3.4 (14)	Cl14—C10—C11—C12	179.6 (10)
C2—C4—C5—O6	−122.1 (10)	C10—C11—C12—C13	−2.9 (19)
C1—C4—C5—N7	−61.4 (11)	C9—C8—C13—C12	−1.1 (13)
C3—C4—C5—N7	−179.7 (9)	N7—C8—C13—C12	−179.3 (9)
C2—C4—C5—N7	61.6 (11)	C11—C12—C13—C8	2.5 (17)
C13—C8—C9—C10	0.2 (14)	O6—C5—N7—C8	5.6 (14)
N7—C8—C9—C10	178.3 (8)	C4—C5—N7—C8	−178.0 (9)
C8—C9—C10—C11	−0.6 (15)	C13—C8—N7—C5	−152.2 (9)
C8—C9—C10—Cl14	−178.3 (7)	C9—C8—N7—C5	29.6 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7N···O6^i	0.86	2.10	2.935 (8)	164

Symmetry code: (i) −x−1/2, y, z−1/2.