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The title compound, C16H21ClO, has a non-planar configuration. The crystal packing is mainly stabilized by intra­molecular C—H...O hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041565/at6065sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041565/at6065Isup2.hkl
Contains datablock I

CCDC reference: 296515

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.070
  • wR factor = 0.195
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C15B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C16B
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.73 mm PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 2 PLAT213_ALERT_2_C Atom O1B has ADP max/min Ratio ............. 3.20 prolat PLAT301_ALERT_3_C Main Residue Disorder ......................... 18.00 Perc.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

It has been shown that 3-substituted cyclobutane carboxylic acid derivatives have antidepressant activities and liquid-crystal properties (Dehmlow & Schmidt, 1990; Roger et al., 1977). Substituted α-haloketones, like the title compound, (I), are used for different purposes, especially in the synthesis of heterocyclic substances (Çukurovalı et al., 2002; Gompper & Christmann, 1959). The extensive synthetic possibilities of this compound, due to the presence of some reaction sites, hold promise for the preparation of new heterocyclic chemicals.

Fig. 1 shows the molecular structure and conformation of (I) with the atomic numbering scheme. The asymmetric unit of (I) consists of cyclobutane and benzene ring linked through a chloroacetaldehyde group. Selected bond lengths and angles in (I) are given in Table 1. Cyclobutane ring A (C1–C4) is not planar and has a CR form, with the puckering parameter Q2 of −0.228 (2) Å (Cremer & Pople, 1975). Literature values for the puckering of the cyclobutane ring are 23.5 (Swenson et al., 1997) and 29.03 (13)° (Yüksektepe et al., 2004). The geometry of the cyclobutane ring is due to the steric effect of the methyl group. The bond lengths and angles in the four-membered ring are normal (Allen et al., 1987). The chloro-acetaldehydes group shows disorder and atoms C15, C16, O1 and Cl1 were studied in two different orientations, with occupancy factors of 0.61 (2) for atoms with suffix A and 0.39 (2) for those with suffix B (Fig. 1).

The crystal structure is stabilized by intramolecular C—H···O hydrogen-bonding interactions.

Experimental top

The synthesis of the title compound was realised according to the literature (Akhmedov et al., 1991) method with some modification as given in the following reaction sequences. The shiny crystals which is suitable for X-ray analysis was obtained by the crystallization from ethanol (yield: 80%, m.p. 366 K). IR (KBr, ν cm−1): 1724 (CO), 732 (—CH2—Cl). 1H NMR (CDCl3): δ 1.63 (s, 3H,CH3 on cyclobutane), 2.22 (s, 3H, p-CH3 on mesitylene), 2.25 (s, 6H, o-CH3 on mesitylene), 2.42–2.78 (m, 4H, —CH2–), 6.80 (s, 2H, aromatics on mesitylene). 13C NMR (CDCl6): δ 48.88 (C1), 205.47 (C2), 41.89 (C3), 42.59 (C4), 26.95 (C5), 40.19 (C6), 145.09 (C7), 132.48 (C8), 132.44 (C9), 136.96 (C10), 22.46 (C11), 23.37 (C12).

Refinement top

H atoms were positioned geometrically and treated using a riding model, fixing the bond lengths at 0.93, 0.96, 0.97 and 0.98 Å for aromatic, methyl, methylene and methine H atoms, respectively. The displacement parameters of the H atoms were constrained to be Uiso(H) = 1.2Ueq of the carrier atom.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); 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); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. An ORTEP-3 (Farrugia, 1997) drawing of (I), showing the atomic numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 30% probability level. The minor occupancy disordered atoms have been omitted.
[Figure 2] Fig. 2. A projection of the molecular packing of (I) along the (100) axis. The minor occupancy disordered atoms have been omitted.
2-Chloro-1-(3 mesitylcyclobutyl)ethanone top
Crystal data top
C16H21ClOF(000) = 568
Mr = 264.78Dx = 1.192 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 26744 reflections
a = 8.3808 (17) Åθ = 2.2–27.9°
b = 15.236 (4) ŵ = 0.25 mm1
c = 12.472 (3) ÅT = 296 K
β = 112.173 (15)°Prism, colorless
V = 1474.8 (6) Å30.73 × 0.57 × 0.37 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
3378 independent reflections
Radiation source: fine-focus sealed tube1993 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
Detector resolution: 6.67 pixels mm-1θmax = 27.8°, θmin = 2.2°
ω scansh = 1010
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1920
Tmin = 0.841, Tmax = 0.914l = 1616
23037 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.1242P)2]
where P = (Fo2 + 2Fc2)/3
3378 reflections(Δ/σ)max < 0.001
197 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C16H21ClOV = 1474.8 (6) Å3
Mr = 264.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.3808 (17) ŵ = 0.25 mm1
b = 15.236 (4) ÅT = 296 K
c = 12.472 (3) Å0.73 × 0.57 × 0.37 mm
β = 112.173 (15)°
Data collection top
Stoe IPDS-2
diffractometer
3378 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
1993 reflections with I > 2σ(I)
Tmin = 0.841, Tmax = 0.914Rint = 0.069
23037 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0700 restraints
wR(F2) = 0.195H-atom parameters constrained
S = 0.96Δρmax = 0.25 e Å3
3378 reflectionsΔρmin = 0.19 e Å3
197 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/UeqOcc. (<1)
Cl1A0.1945 (5)1.1329 (3)0.4417 (4)0.0970 (10)0.61 (2)
O1A0.2786 (15)0.9432 (6)0.4459 (8)0.132 (3)0.61 (2)
C10.2841 (3)0.80638 (17)0.6095 (2)0.0782 (8)
C20.2973 (4)0.90445 (17)0.6343 (2)0.0786 (9)
C30.4857 (2)0.88921 (10)0.71726 (12)0.0763 (8)
C40.4478 (2)0.79103 (10)0.71928 (12)0.0678 (8)
C50.4014 (2)0.76722 (10)0.82605 (12)0.0933 (11)
C60.5814 (3)0.72618 (13)0.71061 (18)0.0588 (7)
C70.5292 (3)0.64812 (14)0.64603 (18)0.0599 (7)
C80.3445 (3)0.61751 (18)0.5950 (3)0.0788 (9)
C90.6510 (3)0.59319 (16)0.63165 (19)0.0652 (8)
C100.8244 (3)0.61018 (17)0.6795 (2)0.0709 (8)
C110.9515 (4)0.5489 (2)0.6602 (3)0.0972 (13)
C120.8754 (3)0.68326 (17)0.7492 (2)0.0725 (8)
C130.7582 (3)0.74067 (15)0.7669 (2)0.0675 (7)
C140.8320 (4)0.81517 (19)0.8522 (2)0.0902 (9)
C15A0.2678 (16)0.9674 (9)0.5334 (10)0.091 (4)0.61 (2)
C16A0.235 (2)1.0574 (7)0.5608 (9)0.088 (3)0.61 (2)
Cl1B0.2091 (12)1.1265 (5)0.4557 (7)0.160 (4)0.39 (2)
C15B0.2710 (19)0.9622 (14)0.5412 (18)0.085 (7)0.39 (2)
C16B0.315 (2)1.0597 (13)0.5670 (15)0.087 (4)0.39 (2)
O1B0.224 (4)0.9414 (10)0.4395 (11)0.193 (7)0.39 (2)
H20.225800.921000.677700.0940*
H3B0.515400.917800.791800.0920*
H5A0.377600.705500.825100.1400*
H3A0.569600.902600.683300.0920*
H1A0.298100.790900.538100.0940*
H1B0.181300.779600.613100.0940*
H8B0.287700.632400.646500.1180*
H8C0.341600.555000.584400.1180*
H90.613700.542600.587600.0780*
H11A0.967900.565500.590800.1460*
H11B0.908400.490000.652600.1460*
H11C1.059600.552300.724800.1460*
H120.992500.694700.785900.0870*
H14A0.948100.801200.902000.1350*
H14B0.763100.823100.898000.1350*
H14C0.831400.868300.810600.1350*
H16A0.334301.077900.626300.1060*0.61 (2)
H16B0.136801.057400.583700.1060*0.61 (2)
H5B0.301500.799900.822500.1400*
H5C0.496500.781700.896100.1400*
H8A0.286600.645600.521600.1180*
H16C0.437901.067600.587800.1050*0.39 (2)
H16D0.288201.076700.633300.1050*0.39 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.121 (2)0.0936 (16)0.0848 (14)0.0389 (11)0.0485 (10)0.0257 (10)
O1A0.218 (7)0.105 (5)0.091 (5)0.070 (5)0.079 (5)0.013 (4)
C10.0734 (15)0.0716 (14)0.0834 (15)0.0037 (11)0.0224 (12)0.0123 (12)
C20.0883 (18)0.0699 (15)0.0777 (15)0.0135 (12)0.0315 (13)0.0067 (12)
C30.0913 (18)0.0639 (13)0.0662 (12)0.0003 (11)0.0213 (12)0.0097 (10)
C40.0778 (15)0.0622 (12)0.0646 (12)0.0013 (10)0.0281 (10)0.0055 (9)
C50.115 (2)0.0938 (19)0.0862 (17)0.0055 (16)0.0553 (17)0.0013 (14)
C60.0634 (13)0.0550 (11)0.0565 (10)0.0048 (9)0.0210 (9)0.0017 (8)
C70.0583 (12)0.0621 (12)0.0577 (10)0.0058 (9)0.0200 (8)0.0019 (8)
C80.0676 (15)0.0683 (14)0.0965 (17)0.0098 (11)0.0266 (13)0.0171 (12)
C90.0670 (14)0.0670 (13)0.0647 (12)0.0016 (10)0.0283 (10)0.0042 (9)
C100.0664 (15)0.0789 (15)0.0724 (13)0.0036 (11)0.0320 (11)0.0090 (11)
C110.0760 (18)0.118 (3)0.105 (2)0.0131 (16)0.0426 (15)0.0007 (17)
C120.0563 (13)0.0808 (16)0.0734 (13)0.0092 (11)0.0165 (10)0.0135 (11)
C130.0678 (14)0.0615 (12)0.0656 (12)0.0108 (10)0.0167 (10)0.0048 (9)
C140.0901 (18)0.0724 (15)0.0832 (16)0.0190 (13)0.0043 (13)0.0054 (12)
C15A0.134 (9)0.071 (6)0.050 (4)0.012 (5)0.016 (4)0.004 (3)
C16A0.126 (8)0.068 (3)0.070 (3)0.020 (6)0.036 (6)0.002 (2)
Cl1B0.293 (11)0.085 (3)0.077 (2)0.048 (3)0.041 (3)0.0206 (17)
C15B0.057 (7)0.097 (13)0.105 (14)0.025 (6)0.035 (7)0.000 (9)
C16B0.098 (9)0.087 (6)0.074 (5)0.012 (8)0.029 (7)0.008 (4)
O1B0.35 (2)0.093 (7)0.056 (5)0.011 (10)0.014 (8)0.023 (4)
Geometric parameters (Å, º) top
Cl1A—C16A1.807 (12)C1—H1A0.9700
Cl1B—C16B1.68 (2)C1—H1B0.9700
O1A—C15A1.187 (16)C2—H20.9800
O1B—C15B1.22 (2)C3—H3A0.9700
C1—C21.521 (4)C3—H3B0.9700
C1—C41.5472C5—H5A0.9600
C2—C31.544 (3)C5—H5B0.9600
C2—C15B1.41 (2)C5—H5C0.9600
C2—C15A1.526 (13)C8—H8A0.9600
C3—C41.5314C8—H8B0.9600
C4—C61.5274C8—H8C0.9600
C4—C51.5643C9—H90.9300
C6—C71.410 (3)C11—H11A0.9600
C6—C131.397 (4)C11—H11B0.9600
C7—C81.508 (4)C11—H11C0.9600
C7—C91.383 (4)C12—H120.9300
C9—C101.371 (4)C14—H14A0.9600
C10—C121.378 (4)C14—H14B0.9600
C10—C111.503 (4)C14—H14C0.9600
C12—C131.394 (4)C16A—H16A0.9700
C13—C141.519 (4)C16A—H16B0.9700
C15A—C16A1.464 (18)C16B—H16C0.9700
C15B—C16B1.54 (3)C16B—H16D0.9700
Cl1A···O1A2.971 (10)H1A···O1A2.5700
Cl1A···C12i3.578 (5)H1A···C82.7200
Cl1A···C13i3.379 (5)H1A···C72.8900
Cl1B···O1B2.834 (17)H1B···H5B2.4400
Cl1B···C13i3.529 (9)H1B···H8B2.3900
Cl1A···H3Ai2.9900H1B···C82.8700
Cl1A···H14Ci3.0700H2···H5B2.4900
Cl1B···H3Ai3.0100H2···H16B2.3600
O1A···Cl1A2.971 (10)H2···C53.0000
O1B···C11ii3.372 (16)H2···H16D2.5400
O1B···Cl1B2.834 (17)H3A···C142.7500
O1A···H1A2.5700H3A···H14C2.2300
O1A···H11Cii2.6800H3A···C132.9000
O1B···H1A2.5700H3A···Cl1Ai2.9900
O1B···H11Cii2.5100H3A···Cl1Bi3.0100
C1···C82.939 (4)H3B···C142.9200
C3···C142.973 (4)H3B···H14B2.4600
C5···C83.5633H3B···H5C2.4800
C5···C143.5742H5A···C83.0800
C7···C16Biii3.578 (18)H5A···H8B2.3500
C8···C53.5633H5A···C73.0800
C8···C12.939 (4)H5A···H16Ciii2.5900
C10···C16Aiii3.550 (13)H5B···C22.8300
C11···O1Biv3.372 (16)H5B···H1B2.4400
C12···C16Aiii3.436 (13)H5B···H22.4900
C12···Cl1Ai3.578 (5)H5C···H14B2.3100
C13···Cl1Bi3.529 (9)H5C···H3B2.4800
C13···C16Aiii3.511 (11)H8A···C12.6900
C13···Cl1Ai3.379 (5)H8A···H1A2.2200
C14···C32.973 (4)H8B···H5A2.3500
C14···C53.5742H8B···C12.6900
C16A···C12v3.436 (13)H8B···C42.7500
C16A···C13v3.511 (11)H8B···H1B2.3900
C16A···C10v3.550 (13)H8B···C52.9200
C16B···C7v3.578 (18)H8C···H92.2700
C1···H8A2.6900H9···H11B2.4300
C1···H8B2.6900H9···H8C2.2700
C2···H5B2.8300H11B···H92.4300
C3···H14C2.7000H11C···H122.4300
C3···H14B2.7500H11C···O1Aiv2.6800
C4···H14B2.7800H11C···O1Biv2.5100
C4···H8B2.7500H12···H14A2.3000
C5···H14B2.9400H12···H11C2.4300
C5···H8B2.9200H14A···H122.3000
C5···H23.0000H14B···H5C2.3100
C6···H16Diii2.9300H14B···C42.7800
C6···H16Aiii2.9400H14B···C52.9400
C7···H5A3.0800H14B···C32.7500
C7···H16Aiii2.8400H14B···H3B2.4600
C7···H16Diii2.8100H14C···H3A2.2300
C7···H1A2.8900H14C···Cl1Ai3.0700
C8···H1B2.8700H14C···C32.7000
C8···H5A3.0800H16A···C7v2.8400
C8···H1A2.7200H16A···C9v2.9800
C9···H16Aiii2.9800H16A···C6v2.9400
C9···H16Diii2.7900H16A···C13v3.0500
C10···H16Diii2.8700H16B···C10v2.9600
C10···H16Biii2.9600H16B···C12v2.8600
C12···H16Diii2.8600H16B···H22.3600
C12···H16Biii2.8600H16C···H5Av2.5900
C13···H16Aiii3.0500H16D···H22.5400
C13···H3A2.9000H16D···C6v2.9300
C13···H16Diii2.8800H16D···C7v2.8100
C14···H3B2.9200H16D···C9v2.7900
C14···H3A2.7500H16D···C10v2.8700
H1A···O1B2.5700H16D···C12v2.8600
H1A···H8A2.2200H16D···C13v2.8800
C2—C1—C489.79C2—C3—H3A114.00
C1—C2—C388.05 (19)C2—C3—H3B114.00
C1—C2—C15A118.2 (5)C4—C3—H3A114.00
C1—C2—C15B118.0 (9)C4—C3—H3B114.00
C3—C2—C15A117.0 (6)H3A—C3—H3B111.00
C3—C2—C15B116.7 (8)C4—C5—H5A109.00
C2—C3—C489.54C4—C5—H5B109.00
C1—C4—C387.59C4—C5—H5C109.00
C1—C4—C5111.48H5A—C5—H5B109.00
C1—C4—C6117.65H5A—C5—H5C109.00
C3—C4—C5111.12H5B—C5—H5C109.00
C3—C4—C6117.94C7—C8—H8A109.00
C5—C4—C6109.55C7—C8—H8B109.00
C4—C6—C7120.55C7—C8—H8C109.00
C4—C6—C13121.94H8A—C8—H8B109.00
C7—C6—C13117.5 (2)H8A—C8—H8C109.00
C6—C7—C8123.3 (2)H8B—C8—H8C109.00
C6—C7—C9120.0 (2)C7—C9—H9119.00
C8—C7—C9116.6 (2)C10—C9—H9119.00
C7—C9—C10122.8 (2)C10—C11—H11A109.00
C9—C10—C11120.8 (2)C10—C11—H11B110.00
C9—C10—C12116.9 (2)C10—C11—H11C109.00
C11—C10—C12122.2 (3)H11A—C11—H11B110.00
C10—C12—C13122.5 (2)H11A—C11—H11C109.00
C6—C13—C12119.9 (2)H11B—C11—H11C110.00
C6—C13—C14123.0 (2)C10—C12—H12119.00
C12—C13—C14117.1 (2)C13—C12—H12119.00
O1A—C15A—C2121.2 (11)C13—C14—H14A109.00
O1A—C15A—C16A126.3 (12)C13—C14—H14B109.00
C2—C15A—C16A112.5 (9)C13—C14—H14C110.00
O1B—C15B—C16B115.3 (18)H14A—C14—H14B109.00
O1B—C15B—C2125.8 (18)H14A—C14—H14C109.00
C2—C15B—C16B118.8 (16)H14B—C14—H14C109.00
Cl1A—C16A—C15A113.5 (8)Cl1A—C16A—H16A109.00
Cl1B—C16B—C15B113.8 (13)Cl1A—C16A—H16B109.00
C2—C1—H1A114.00C15A—C16A—H16A109.00
C2—C1—H1B114.00C15A—C16A—H16B109.00
C4—C1—H1A114.00H16A—C16A—H16B108.00
C4—C1—H1B114.00Cl1B—C16B—H16C109.00
H1A—C1—H1B111.00Cl1B—C16B—H16D109.00
C1—C2—H2111.00C15B—C16B—H16C109.00
C3—C2—H2111.00C15B—C16B—H16D109.00
C15A—C2—H2111.00H16C—C16B—H16D108.00
C15B—C2—H2111.00
C4—C1—C2—C316.79C5—C4—C6—C1389.22
C4—C1—C2—C15A136.57C4—C6—C7—C88.04
C2—C1—C4—C316.94C4—C6—C7—C9175.15
C2—C1—C4—C594.83C13—C6—C7—C8171.0 (2)
C2—C1—C4—C6137.43C13—C6—C7—C95.8 (3)
C1—C2—C3—C416.97C4—C6—C13—C12174.95
C15A—C2—C3—C4137.87C4—C6—C13—C147.66
C1—C2—C15A—O1A19.2 (16)C7—C6—C13—C126.0 (3)
C1—C2—C15A—C16A163.5 (9)C7—C6—C13—C14171.4 (2)
C3—C2—C15A—O1A84.1 (13)C6—C7—C9—C101.1 (3)
C3—C2—C15A—C16A93.2 (11)C8—C7—C9—C10175.9 (2)
C2—C3—C4—C116.69C7—C9—C10—C11179.3 (2)
C2—C3—C4—C595.43C7—C9—C10—C123.4 (4)
C2—C3—C4—C6136.91C9—C10—C12—C133.2 (4)
C1—C4—C6—C738.84C11—C10—C12—C13179.6 (2)
C1—C4—C6—C13142.13C10—C12—C13—C61.6 (4)
C3—C4—C6—C7141.79C10—C12—C13—C14176.0 (2)
C3—C4—C6—C1339.18O1A—C15A—C16A—Cl1A4 (2)
C5—C4—C6—C789.81C2—C15A—C16A—Cl1A178.6 (8)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x1, y+3/2, z1/2; (iii) x+1, y1/2, z+3/2; (iv) x+1, y+3/2, z+1/2; (v) x+1, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O1A0.972.572.905 (10)100

Experimental details

Crystal data
Chemical formulaC16H21ClO
Mr264.78
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)8.3808 (17), 15.236 (4), 12.472 (3)
β (°) 112.173 (15)
V3)1474.8 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.73 × 0.57 × 0.37
Data collection
DiffractometerStoe IPDS2
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.841, 0.914
No. of measured, independent and
observed [I > 2σ(I)] reflections
23037, 3378, 1993
Rint0.069
(sin θ/λ)max1)0.657
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.195, 0.96
No. of reflections3378
No. of parameters197
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.19

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
Cl1A—C16A1.807 (12)O1A—C15A1.187 (16)
Cl1B—C16B1.68 (2)O1B—C15B1.22 (2)
O1A—C15A—C2121.2 (11)O1B—C15B—C2125.8 (18)
O1A—C15A—C16A126.3 (12)Cl1A—C16A—C15A113.5 (8)
O1B—C15B—C16B115.3 (18)Cl1B—C16B—C15B113.8 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O1A0.972.572.905 (10)100
 

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