Weak C—H...O hydrogen bonding and aromatic π–π-stacking interactions in 1-(4-chloro­phenyl)­propan-1-one

The supramolecular structure of this low melting point compound, C₉H₉ClO, is characterized by weak C—H...O hydrogen bonding and π–π stacking of aromatic rings.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.086
• Data-to-parameter ratio = 10.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.46
         From the CIF: _reflns_number_total               1292
         Count of symmetry unique reflns         1093
         Completeness (_total/calc)            118.21%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       199
         Fraction of Friedel pairs measured     0.182
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure

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Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2001).

1-(4-chlorophenyl)propane-1-one

Crystal data

C9H9ClO	Dx = 1.344 Mg m^−3
Mr = 168.61	Melting point: 34-37°C K
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
a = 18.6188 (14) Å	Cell parameters from 7501 reflections
b = 45.383 (4) Å	θ = 2.9–27.5°
c = 3.945 (4) Å	µ = 0.39 mm^−1
V = 3334 (3) Å^3	T = 120 K
Z = 16	Block, colourless
F(000) = 1408	0.20 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1292 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1105 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
Detector resolution: 3.89 pixels mm^-1	θmax = 27.5°, θmin = 3.5°
φ and ω scans	h = −23→24
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −58→58
Tmin = 0.926, Tmax = 0.969	l = −2→5
4434 measured reflections

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)] = 0.039	Only H-atom coordinates refined
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0501P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
1292 reflections	Δρmax = 0.25 e Å^−3
127 parameters	Δρmin = −0.29 e Å^−3
1 restraint	Absolute structure: Flack (1983); 367 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (9)

Special details

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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	0.61345 (4)	−0.009870 (14)	0.4085 (2)	0.0358 (3)
O1	0.72784 (10)	0.12185 (4)	−0.1196 (7)	0.0315 (5)
C1	0.65715 (12)	0.08514 (5)	0.1415 (9)	0.0185 (6)
C2	0.59392 (14)	0.07742 (6)	0.3081 (8)	0.0231 (7)
H2	0.5599 (14)	0.0928 (6)	0.361 (8)	0.028*
C3	0.57998 (14)	0.04813 (5)	0.3876 (9)	0.0235 (6)
H3	0.5344 (16)	0.0432 (5)	0.509 (7)	0.028*
C4	0.62994 (14)	0.02687 (5)	0.3014 (7)	0.0237 (7)
C5	0.69320 (15)	0.03401 (5)	0.1359 (9)	0.0251 (7)
H5	0.7264 (15)	0.0192 (6)	0.067 (8)	0.030*
C6	0.70658 (16)	0.06301 (6)	0.0560 (8)	0.0241 (7)
H6	0.7512 (15)	0.0673 (5)	−0.067 (9)	0.029*
C7	0.67426 (15)	0.11631 (6)	0.0441 (8)	0.0212 (7)
C8	0.62391 (15)	0.14059 (5)	0.1544 (10)	0.0229 (6)
H8A	0.6148 (14)	0.1393 (6)	0.377 (10)	0.028*
H8B	0.5770 (16)	0.1370 (5)	0.039 (8)	0.028*
C9	0.65111 (18)	0.17135 (6)	0.0768 (9)	0.0270 (8)
H9A	0.7000 (16)	0.1743 (6)	0.183 (10)	0.035*
H9B	0.6154 (14)	0.1855 (6)	0.156 (10)	0.035*
H9C	0.6568 (17)	0.1726 (6)	−0.168 (10)	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0389 (4)	0.0183 (3)	0.0503 (6)	−0.0013 (3)	−0.0004 (4)	0.0039 (3)
O1	0.0225 (10)	0.0305 (10)	0.0417 (14)	−0.0021 (8)	0.0116 (11)	0.0053 (11)
C1	0.0142 (13)	0.0213 (12)	0.0200 (17)	0.0008 (9)	−0.0024 (15)	−0.0009 (12)
C2	0.0177 (14)	0.0231 (14)	0.029 (2)	0.0020 (10)	−0.0027 (13)	−0.0020 (11)
C3	0.0210 (15)	0.0250 (13)	0.0244 (18)	−0.0017 (10)	0.0012 (16)	0.0015 (13)
C4	0.0296 (16)	0.0178 (12)	0.024 (2)	−0.0022 (10)	−0.0115 (13)	0.0018 (11)
C5	0.0241 (15)	0.0247 (13)	0.0264 (19)	0.0052 (11)	−0.0004 (16)	−0.0038 (14)
C6	0.0179 (14)	0.0284 (14)	0.026 (2)	0.0000 (11)	0.0005 (13)	−0.0008 (12)
C7	0.0172 (15)	0.0257 (13)	0.0208 (18)	−0.0013 (10)	−0.0062 (13)	0.0006 (10)
C8	0.0242 (16)	0.0216 (12)	0.0230 (18)	−0.0019 (10)	0.0015 (17)	0.0005 (13)
C9	0.0336 (18)	0.0224 (14)	0.025 (2)	−0.0012 (12)	−0.0035 (17)	0.0010 (12)

Geometric parameters (Å, º)

Cl1—C4	1.747 (3)	C5—C6	1.376 (4)
O1—C7	1.215 (3)	C5—H5	0.95 (3)
C1—C2	1.393 (4)	C6—H6	0.98 (3)
C1—C6	1.403 (4)	C7—C8	1.511 (4)
C1—C7	1.500 (4)	C8—C9	1.516 (4)
C2—C3	1.390 (4)	C8—H8A	0.90 (4)
C2—H2	0.97 (3)	C8—H8B	1.00 (3)
C3—C4	1.383 (4)	C9—H9A	1.01 (3)
C3—H3	1.00 (3)	C9—H9B	0.98 (3)
C4—C5	1.385 (4)	C9—H9C	0.97 (4)
C2—C1—C6	119.2 (2)	C1—C6—H6	122.0 (14)
C2—C1—C7	122.5 (2)	O1—C7—C1	120.4 (2)
C6—C1—C7	118.3 (2)	O1—C7—C8	120.8 (2)
C3—C2—C1	120.3 (2)	C1—C7—C8	118.8 (2)
C3—C2—H2	121.4 (16)	C7—C8—C9	114.0 (2)
C1—C2—H2	118.3 (16)	C7—C8—H8A	110.5 (17)
C4—C3—C2	119.1 (3)	C9—C8—H8A	108.8 (17)
C4—C3—H3	122.2 (14)	C7—C8—H8B	107.1 (15)
C2—C3—H3	118.7 (14)	C9—C8—H8B	110.5 (15)
C3—C4—C5	121.7 (2)	H8A—C8—H8B	106 (3)
C3—C4—Cl1	119.2 (2)	C8—C9—H9A	109.8 (16)
C5—C4—Cl1	119.10 (19)	C8—C9—H9B	108.4 (17)
C6—C5—C4	119.0 (3)	H9A—C9—H9B	113 (3)
C6—C5—H5	119.6 (17)	C8—C9—H9C	106.8 (18)
C4—C5—H5	121.3 (16)	H9A—C9—H9C	108 (3)
C5—C6—C1	120.7 (3)	H9B—C9—H9C	111 (3)
C5—C6—H6	117.3 (14)
C6—C1—C2—C3	−0.2 (5)	C2—C1—C6—C5	−0.2 (5)
C7—C1—C2—C3	178.8 (3)	C7—C1—C6—C5	−179.3 (3)
C1—C2—C3—C4	0.5 (5)	C2—C1—C7—O1	−175.4 (3)
C2—C3—C4—C5	−0.5 (5)	C6—C1—C7—O1	3.7 (4)
C2—C3—C4—Cl1	178.7 (2)	C2—C1—C7—C8	4.9 (4)
C3—C4—C5—C6	0.1 (5)	C6—C1—C7—C8	−176.1 (3)
Cl1—C4—C5—C6	−179.1 (2)	O1—C7—C8—C9	−6.5 (5)
C4—C5—C6—C1	0.3 (5)	C1—C7—C8—C9	173.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.97 (3)	2.46 (3)	3.404 (5)	167 (3)
C8—H8B···O1^ii	1.00 (3)	2.48 (3)	3.462 (5)	167 (3)

Symmetry codes: (i) x−1/4, −y+1/4, z+3/4; (ii) x−1/4, −y+1/4, z−1/4.