(2-Chloro­anilino)acetophenone

The title compound, C₁₄H₁₂ClNO, is used in perfumery, as a catalyst for the polymerization of olefins, and in organic synthesis, especially as a photosensitizer and in the manufacture of dyes. The mol­ecule is essentially planar and has a trans configuration. In this configuration, the Cl and O atoms shield the amino H atom, preventing the formation of an inter­molecular hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.050
• wR factor = 0.146
• Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.02
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.35
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
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           25.38
           From the CIF: _reflns_number_total               1169
           Count of symmetry unique reflns         1178
           Completeness (_total/calc)             99.24%
           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        yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON.

(2-Chloroanilino)acetophenone

Crystal data

C14H12ClNO	F(000) = 512
Mr = 245.70	Dx = 1.344 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 7972 reflections
a = 18.363 (4) Å	θ = 2.8–25.6°
b = 5.2852 (14) Å	µ = 0.30 mm^−1
c = 12.509 (2) Å	T = 173 K
V = 1214.0 (5) Å^3	Needle, colourless
Z = 4	0.33 × 0.12 × 0.12 mm

Data collection

Stoe IPDS-II two-circle diffractometer	1169 independent reflections
Radiation source: fine-focus sealed tube	986 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
ω scans	θmax = 25.4°, θmin = 2.8°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −18→22
Tmin = 0.909, Tmax = 0.945	k = −6→5
3857 measured reflections	l = −15→15

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.146	w = 1/[σ^2(Fo^2) + (0.096P)^2 + 0.1628P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1169 reflections	Δρmax = 0.30 e Å^−3
159 parameters	Δρmin = −0.30 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (8)

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
Cl1	0.32805 (7)	0.2392 (3)	0.71688 (14)	0.0573 (5)
O1	0.4946 (2)	0.8954 (7)	0.6996 (3)	0.0553 (10)
N1	0.4228 (2)	0.5632 (8)	0.5793 (4)	0.0472 (10)
H1	0.423 (3)	0.579 (9)	0.645 (5)	0.034 (13)*
C1	0.4717 (3)	0.7342 (9)	0.5258 (4)	0.0433 (11)
H1A	0.4443	0.8350	0.4726	0.052*
H1B	0.5094	0.6360	0.4873	0.052*
C2	0.5077 (2)	0.9093 (9)	0.6049 (4)	0.0419 (11)
C11	0.3844 (3)	0.3807 (9)	0.5253 (4)	0.0425 (11)
C12	0.3371 (2)	0.2114 (10)	0.5794 (5)	0.0438 (11)
C13	0.2980 (3)	0.0253 (10)	0.5259 (4)	0.0497 (12)
H13	0.2669	−0.0851	0.5648	0.060*
C14	0.3042 (3)	0.0003 (11)	0.4165 (5)	0.0514 (12)
H14	0.2774	−0.1263	0.3796	0.062*
C15	0.3505 (3)	0.1639 (10)	0.3605 (4)	0.0491 (12)
H15	0.3556	0.1468	0.2852	0.059*
C16	0.3893 (3)	0.3518 (10)	0.4144 (4)	0.0469 (12)
H16	0.4197	0.4629	0.3748	0.056*
C21	0.5610 (3)	1.1005 (9)	0.5606 (4)	0.0416 (11)
C22	0.5754 (3)	1.1142 (10)	0.4518 (4)	0.0462 (12)
H22	0.5512	1.0045	0.4032	0.055*
C23	0.6261 (3)	1.2916 (10)	0.4144 (5)	0.0490 (12)
H23	0.6365	1.3011	0.3401	0.059*
C24	0.6613 (3)	1.4537 (10)	0.4849 (5)	0.0512 (13)
H24	0.6953	1.5739	0.4587	0.061*
C25	0.6468 (3)	1.4406 (10)	0.5927 (4)	0.0491 (12)
H25	0.6709	1.5514	0.6409	0.059*
C26	0.5962 (3)	1.2627 (9)	0.6316 (4)	0.0466 (11)
H26	0.5861	1.2533	0.7060	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0554 (7)	0.0669 (8)	0.0495 (7)	−0.0078 (6)	0.0089 (6)	0.0006 (6)
O1	0.050 (2)	0.072 (2)	0.043 (2)	−0.0103 (18)	0.0018 (16)	−0.0006 (17)
N1	0.048 (2)	0.047 (2)	0.046 (2)	−0.0053 (19)	0.0016 (19)	−0.0024 (19)
C1	0.038 (2)	0.044 (3)	0.048 (3)	−0.003 (2)	0.000 (2)	0.002 (2)
C2	0.033 (2)	0.042 (3)	0.050 (3)	0.001 (2)	0.001 (2)	0.001 (2)
C11	0.036 (2)	0.042 (3)	0.049 (3)	0.002 (2)	−0.002 (2)	0.002 (2)
C12	0.035 (2)	0.047 (3)	0.050 (3)	0.001 (2)	0.002 (2)	0.004 (2)
C13	0.037 (3)	0.049 (3)	0.063 (3)	−0.005 (2)	0.001 (2)	0.002 (3)
C14	0.038 (2)	0.052 (3)	0.064 (3)	0.000 (2)	−0.007 (2)	0.000 (2)
C15	0.047 (3)	0.054 (3)	0.046 (3)	0.004 (3)	−0.003 (2)	0.003 (2)
C16	0.041 (3)	0.047 (3)	0.053 (3)	−0.002 (2)	−0.002 (2)	0.003 (2)
C21	0.032 (2)	0.042 (3)	0.050 (3)	0.0016 (19)	−0.0004 (19)	−0.001 (2)
C22	0.039 (2)	0.050 (3)	0.050 (3)	−0.001 (2)	0.000 (2)	0.002 (2)
C23	0.040 (3)	0.056 (3)	0.051 (3)	−0.001 (2)	0.004 (2)	0.000 (2)
C24	0.042 (3)	0.043 (3)	0.068 (4)	−0.001 (2)	0.001 (2)	0.000 (2)
C25	0.043 (2)	0.043 (3)	0.061 (3)	0.002 (2)	−0.007 (2)	−0.005 (2)
C26	0.043 (3)	0.049 (3)	0.049 (3)	0.000 (2)	−0.004 (2)	−0.002 (2)

Geometric parameters (Å, º)

Cl1—C12	1.734 (6)	C14—H14	0.9500
O1—C2	1.210 (6)	C15—C16	1.396 (7)
N1—C11	1.372 (7)	C15—H15	0.9500
N1—C1	1.439 (6)	C16—H16	0.9500
N1—H1	0.82 (6)	C21—C22	1.389 (7)
C1—C2	1.508 (7)	C21—C26	1.393 (7)
C1—H1A	0.9900	C22—C23	1.402 (7)
C1—H1B	0.9900	C22—H22	0.9500
C2—C21	1.511 (6)	C23—C24	1.389 (8)
C11—C16	1.398 (7)	C23—H23	0.9500
C11—C12	1.419 (7)	C24—C25	1.376 (8)
C12—C13	1.390 (8)	C24—H24	0.9500
C13—C14	1.380 (8)	C25—C26	1.408 (8)
C13—H13	0.9500	C25—H25	0.9500
C14—C15	1.401 (8)	C26—H26	0.9500
C11—N1—C1	122.2 (4)	C16—C15—C14	120.4 (5)
C11—N1—H1	124 (3)	C16—C15—H15	119.8
C1—N1—H1	113 (3)	C14—C15—H15	119.8
N1—C1—C2	110.7 (4)	C15—C16—C11	121.7 (5)
N1—C1—H1A	109.5	C15—C16—H16	119.2
C2—C1—H1A	109.5	C11—C16—H16	119.2
N1—C1—H1B	109.5	C22—C21—C26	120.2 (5)
C2—C1—H1B	109.5	C22—C21—C2	121.2 (4)
H1A—C1—H1B	108.1	C26—C21—C2	118.6 (4)
O1—C2—C1	121.1 (5)	C21—C22—C23	119.3 (5)
O1—C2—C21	121.9 (4)	C21—C22—H22	120.4
C1—C2—C21	117.0 (4)	C23—C22—H22	120.4
N1—C11—C16	122.2 (5)	C24—C23—C22	120.6 (5)
N1—C11—C12	121.5 (5)	C24—C23—H23	119.7
C16—C11—C12	116.3 (5)	C22—C23—H23	119.7
C13—C12—C11	122.2 (5)	C25—C24—C23	120.1 (5)
C13—C12—Cl1	119.2 (4)	C25—C24—H24	119.9
C11—C12—Cl1	118.6 (4)	C23—C24—H24	119.9
C14—C13—C12	120.2 (5)	C24—C25—C26	120.0 (5)
C14—C13—H13	119.9	C24—C25—H25	120.0
C12—C13—H13	119.9	C26—C25—H25	120.0
C13—C14—C15	119.2 (5)	C21—C26—C25	119.8 (5)
C13—C14—H14	120.4	C21—C26—H26	120.1
C15—C14—H14	120.4	C25—C26—H26	120.1
C11—N1—C1—C2	−178.5 (4)	N1—C11—C16—C15	179.4 (5)
N1—C1—C2—O1	0.3 (7)	C12—C11—C16—C15	−1.0 (7)
N1—C1—C2—C21	179.9 (4)	O1—C2—C21—C22	−179.9 (5)
C1—N1—C11—C16	−1.2 (7)	C1—C2—C21—C22	0.4 (6)
C1—N1—C11—C12	179.2 (4)	O1—C2—C21—C26	0.7 (7)
N1—C11—C12—C13	−179.8 (5)	C1—C2—C21—C26	−178.9 (5)
C16—C11—C12—C13	0.5 (7)	C26—C21—C22—C23	0.4 (7)
N1—C11—C12—Cl1	0.1 (6)	C2—C21—C22—C23	−178.9 (4)
C16—C11—C12—Cl1	−179.5 (4)	C21—C22—C23—C24	−0.5 (7)
C11—C12—C13—C14	−0.2 (8)	C22—C23—C24—C25	0.3 (7)
Cl1—C12—C13—C14	179.8 (4)	C23—C24—C25—C26	−0.1 (7)
C12—C13—C14—C15	0.3 (8)	C22—C21—C26—C25	−0.2 (7)
C13—C14—C15—C16	−0.8 (8)	C2—C21—C26—C25	179.2 (4)
C14—C15—C16—C11	1.2 (8)	C24—C25—C26—C21	0.0 (7)