In the structure of the title compound (3CPTMA), C
11H
14ClNO, 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.
Supporting information
CCDC reference: 613409
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (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
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
top
Crystal data top
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) Å3 | Needle, colourless |
Z = 4 | 0.68 × 0.05 × 0.03 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.071 | H-atom parameters constrained |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.0368P)2] where P = (Fo2 + 2Fc2)/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 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 | −0.4773 (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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7N···O6i | 0.86 | 2.10 | 2.935 (8) | 164 |
Symmetry code: (i) −x−1/2, y, z−1/2. |