2-Chloro-1-(3-mesityl-3-methylcyclo­butyl)ethanone

Demir, S.; Dinçer, M.; Çukurovalı, A.; Yılmaz, I.

doi:10.1107/S1600536805041565

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2-Chloro-1-(3-mesityl-3-methylcyclobutyl)ethanone

S. Demir, M. Dinçer, A. Çukurovalı and I. Yılmaz

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

O hydrogen-bonding interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041565/at6065sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041565/at6065Isup2.hkl Contains datablock I

CCDC reference: 296515

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (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 (C═O), 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).

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

	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.
	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

C₁₆H₂₁ClO	F(000) = 568
M_r = 264.78	D_x = 1.192 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 26744 reflections
a = 8.3808 (17) Å	θ = 2.2–27.9°
b = 15.236 (4) Å	µ = 0.25 mm⁻¹
c = 12.472 (3) Å	T = 296 K
β = 112.173 (15)°	Prism, colorless
V = 1474.8 (6) Å³	0.73 × 0.57 × 0.37 mm
Z = 4

Data collection top

Stoe IPDS-2 diffractometer	3378 independent reflections
Radiation source: fine-focus sealed tube	1993 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.8°, θ_min = 2.2°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −19→20
T_min = 0.841, T_max = 0.914	l = −16→16
23037 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.1242P)²] where P = (F_o² + 2F_c²)/3
3378 reflections	(Δ/σ)_max < 0.001
197 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₆H₂₁ClO	V = 1474.8 (6) Å³
M_r = 264.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3808 (17) Å	µ = 0.25 mm⁻¹
b = 15.236 (4) Å	T = 296 K
c = 12.472 (3) Å	0.73 × 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)
T_min = 0.841, T_max = 0.914	R_int = 0.069
23037 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 0.96	Δρ_max = 0.25 e Å⁻³
3378 reflections	Δρ_min = −0.19 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1A	0.1945 (5)	1.1329 (3)	0.4417 (4)	0.0970 (10)	0.61 (2)
O1A	0.2786 (15)	0.9432 (6)	0.4459 (8)	0.132 (3)	0.61 (2)
C1	0.2841 (3)	0.80638 (17)	0.6095 (2)	0.0782 (8)
C2	0.2973 (4)	0.90445 (17)	0.6343 (2)	0.0786 (9)
C3	0.4857 (2)	0.88921 (10)	0.71726 (12)	0.0763 (8)
C4	0.4478 (2)	0.79103 (10)	0.71928 (12)	0.0678 (8)
C5	0.4014 (2)	0.76722 (10)	0.82605 (12)	0.0933 (11)
C6	0.5814 (3)	0.72618 (13)	0.71061 (18)	0.0588 (7)
C7	0.5292 (3)	0.64812 (14)	0.64603 (18)	0.0599 (7)
C8	0.3445 (3)	0.61751 (18)	0.5950 (3)	0.0788 (9)
C9	0.6510 (3)	0.59319 (16)	0.63165 (19)	0.0652 (8)
C10	0.8244 (3)	0.61018 (17)	0.6795 (2)	0.0709 (8)
C11	0.9515 (4)	0.5489 (2)	0.6602 (3)	0.0972 (13)
C12	0.8754 (3)	0.68326 (17)	0.7492 (2)	0.0725 (8)
C13	0.7582 (3)	0.74067 (15)	0.7669 (2)	0.0675 (7)
C14	0.8320 (4)	0.81517 (19)	0.8522 (2)	0.0902 (9)
C15A	0.2678 (16)	0.9674 (9)	0.5334 (10)	0.091 (4)	0.61 (2)
C16A	0.235 (2)	1.0574 (7)	0.5608 (9)	0.088 (3)	0.61 (2)
Cl1B	0.2091 (12)	1.1265 (5)	0.4557 (7)	0.160 (4)	0.39 (2)
C15B	0.2710 (19)	0.9622 (14)	0.5412 (18)	0.085 (7)	0.39 (2)
C16B	0.315 (2)	1.0597 (13)	0.5670 (15)	0.087 (4)	0.39 (2)
O1B	0.224 (4)	0.9414 (10)	0.4395 (11)	0.193 (7)	0.39 (2)
H2	0.22580	0.92100	0.67770	0.0940*
H3B	0.51540	0.91780	0.79180	0.0920*
H5A	0.37760	0.70550	0.82510	0.1400*
H3A	0.56960	0.90260	0.68330	0.0920*
H1A	0.29810	0.79090	0.53810	0.0940*
H1B	0.18130	0.77960	0.61310	0.0940*
H8B	0.28770	0.63240	0.64650	0.1180*
H8C	0.34160	0.55500	0.58440	0.1180*
H9	0.61370	0.54260	0.58760	0.0780*
H11A	0.96790	0.56550	0.59080	0.1460*
H11B	0.90840	0.49000	0.65260	0.1460*
H11C	1.05960	0.55230	0.72480	0.1460*
H12	0.99250	0.69470	0.78590	0.0870*
H14A	0.94810	0.80120	0.90200	0.1350*
H14B	0.76310	0.82310	0.89800	0.1350*
H14C	0.83140	0.86830	0.81060	0.1350*
H16A	0.33430	1.07790	0.62630	0.1060*	0.61 (2)
H16B	0.13680	1.05740	0.58370	0.1060*	0.61 (2)
H5B	0.30150	0.79990	0.82250	0.1400*
H5C	0.49650	0.78170	0.89610	0.1400*
H8A	0.28660	0.64560	0.52160	0.1180*
H16C	0.43790	1.06760	0.58780	0.1050*	0.39 (2)
H16D	0.28820	1.07670	0.63330	0.1050*	0.39 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1A	0.121 (2)	0.0936 (16)	0.0848 (14)	0.0389 (11)	0.0485 (10)	0.0257 (10)
O1A	0.218 (7)	0.105 (5)	0.091 (5)	0.070 (5)	0.079 (5)	0.013 (4)
C1	0.0734 (15)	0.0716 (14)	0.0834 (15)	0.0037 (11)	0.0224 (12)	−0.0123 (12)
C2	0.0883 (18)	0.0699 (15)	0.0777 (15)	0.0135 (12)	0.0315 (13)	−0.0067 (12)
C3	0.0913 (18)	0.0639 (13)	0.0662 (12)	−0.0003 (11)	0.0213 (12)	−0.0097 (10)
C4	0.0778 (15)	0.0622 (12)	0.0646 (12)	−0.0013 (10)	0.0281 (10)	−0.0055 (9)
C5	0.115 (2)	0.0938 (19)	0.0862 (17)	0.0055 (16)	0.0553 (17)	0.0013 (14)
C6	0.0634 (13)	0.0550 (11)	0.0565 (10)	−0.0048 (9)	0.0210 (9)	0.0017 (8)
C7	0.0583 (12)	0.0621 (12)	0.0577 (10)	−0.0058 (9)	0.0200 (8)	−0.0019 (8)
C8	0.0676 (15)	0.0683 (14)	0.0965 (17)	−0.0098 (11)	0.0266 (13)	−0.0171 (12)
C9	0.0670 (14)	0.0670 (13)	0.0647 (12)	−0.0016 (10)	0.0283 (10)	−0.0042 (9)
C10	0.0664 (15)	0.0789 (15)	0.0724 (13)	0.0036 (11)	0.0320 (11)	0.0090 (11)
C11	0.0760 (18)	0.118 (3)	0.105 (2)	0.0131 (16)	0.0426 (15)	0.0007 (17)
C12	0.0563 (13)	0.0808 (16)	0.0734 (13)	−0.0092 (11)	0.0165 (10)	0.0135 (11)
C13	0.0678 (14)	0.0615 (12)	0.0656 (12)	−0.0108 (10)	0.0167 (10)	0.0048 (9)
C14	0.0901 (18)	0.0724 (15)	0.0832 (16)	−0.0190 (13)	0.0043 (13)	−0.0054 (12)
C15A	0.134 (9)	0.071 (6)	0.050 (4)	0.012 (5)	0.016 (4)	−0.004 (3)
C16A	0.126 (8)	0.068 (3)	0.070 (3)	0.020 (6)	0.036 (6)	0.002 (2)
Cl1B	0.293 (11)	0.085 (3)	0.077 (2)	0.048 (3)	0.041 (3)	0.0206 (17)
C15B	0.057 (7)	0.097 (13)	0.105 (14)	0.025 (6)	0.035 (7)	0.000 (9)
C16B	0.098 (9)	0.087 (6)	0.074 (5)	0.012 (8)	0.029 (7)	−0.008 (4)
O1B	0.35 (2)	0.093 (7)	0.056 (5)	−0.011 (10)	−0.014 (8)	−0.023 (4)

Geometric parameters (Å, º) top

Cl1A—C16A	1.807 (12)	C1—H1A	0.9700
Cl1B—C16B	1.68 (2)	C1—H1B	0.9700
O1A—C15A	1.187 (16)	C2—H2	0.9800
O1B—C15B	1.22 (2)	C3—H3A	0.9700
C1—C2	1.521 (4)	C3—H3B	0.9700
C1—C4	1.5472	C5—H5A	0.9600
C2—C3	1.544 (3)	C5—H5B	0.9600
C2—C15B	1.41 (2)	C5—H5C	0.9600
C2—C15A	1.526 (13)	C8—H8A	0.9600
C3—C4	1.5314	C8—H8B	0.9600
C4—C6	1.5274	C8—H8C	0.9600
C4—C5	1.5643	C9—H9	0.9300
C6—C7	1.410 (3)	C11—H11A	0.9600
C6—C13	1.397 (4)	C11—H11B	0.9600
C7—C8	1.508 (4)	C11—H11C	0.9600
C7—C9	1.383 (4)	C12—H12	0.9300
C9—C10	1.371 (4)	C14—H14A	0.9600
C10—C12	1.378 (4)	C14—H14B	0.9600
C10—C11	1.503 (4)	C14—H14C	0.9600
C12—C13	1.394 (4)	C16A—H16A	0.9700
C13—C14	1.519 (4)	C16A—H16B	0.9700
C15A—C16A	1.464 (18)	C16B—H16C	0.9700
C15B—C16B	1.54 (3)	C16B—H16D	0.9700

Cl1A···O1A	2.971 (10)	H1A···O1A	2.5700
Cl1A···C12ⁱ	3.578 (5)	H1A···C8	2.7200
Cl1A···C13ⁱ	3.379 (5)	H1A···C7	2.8900
Cl1B···O1B	2.834 (17)	H1B···H5B	2.4400
Cl1B···C13ⁱ	3.529 (9)	H1B···H8B	2.3900
Cl1A···H3Aⁱ	2.9900	H1B···C8	2.8700
Cl1A···H14Cⁱ	3.0700	H2···H5B	2.4900
Cl1B···H3Aⁱ	3.0100	H2···H16B	2.3600
O1A···Cl1A	2.971 (10)	H2···C5	3.0000
O1B···C11ⁱⁱ	3.372 (16)	H2···H16D	2.5400
O1B···Cl1B	2.834 (17)	H3A···C14	2.7500
O1A···H1A	2.5700	H3A···H14C	2.2300
O1A···H11Cⁱⁱ	2.6800	H3A···C13	2.9000
O1B···H1A	2.5700	H3A···Cl1Aⁱ	2.9900
O1B···H11Cⁱⁱ	2.5100	H3A···Cl1Bⁱ	3.0100
C1···C8	2.939 (4)	H3B···C14	2.9200
C3···C14	2.973 (4)	H3B···H14B	2.4600
C5···C8	3.5633	H3B···H5C	2.4800
C5···C14	3.5742	H5A···C8	3.0800
C7···C16Bⁱⁱⁱ	3.578 (18)	H5A···H8B	2.3500
C8···C5	3.5633	H5A···C7	3.0800
C8···C1	2.939 (4)	H5A···H16Cⁱⁱⁱ	2.5900
C10···C16Aⁱⁱⁱ	3.550 (13)	H5B···C2	2.8300
C11···O1B^iv	3.372 (16)	H5B···H1B	2.4400
C12···C16Aⁱⁱⁱ	3.436 (13)	H5B···H2	2.4900
C12···Cl1Aⁱ	3.578 (5)	H5C···H14B	2.3100
C13···Cl1Bⁱ	3.529 (9)	H5C···H3B	2.4800
C13···C16Aⁱⁱⁱ	3.511 (11)	H8A···C1	2.6900
C13···Cl1Aⁱ	3.379 (5)	H8A···H1A	2.2200
C14···C3	2.973 (4)	H8B···H5A	2.3500
C14···C5	3.5742	H8B···C1	2.6900
C16A···C12^v	3.436 (13)	H8B···C4	2.7500
C16A···C13^v	3.511 (11)	H8B···H1B	2.3900
C16A···C10^v	3.550 (13)	H8B···C5	2.9200
C16B···C7^v	3.578 (18)	H8C···H9	2.2700
C1···H8A	2.6900	H9···H11B	2.4300
C1···H8B	2.6900	H9···H8C	2.2700
C2···H5B	2.8300	H11B···H9	2.4300
C3···H14C	2.7000	H11C···H12	2.4300
C3···H14B	2.7500	H11C···O1A^iv	2.6800
C4···H14B	2.7800	H11C···O1B^iv	2.5100
C4···H8B	2.7500	H12···H14A	2.3000
C5···H14B	2.9400	H12···H11C	2.4300
C5···H8B	2.9200	H14A···H12	2.3000
C5···H2	3.0000	H14B···H5C	2.3100
C6···H16Dⁱⁱⁱ	2.9300	H14B···C4	2.7800
C6···H16Aⁱⁱⁱ	2.9400	H14B···C5	2.9400
C7···H5A	3.0800	H14B···C3	2.7500
C7···H16Aⁱⁱⁱ	2.8400	H14B···H3B	2.4600
C7···H16Dⁱⁱⁱ	2.8100	H14C···H3A	2.2300
C7···H1A	2.8900	H14C···Cl1Aⁱ	3.0700
C8···H1B	2.8700	H14C···C3	2.7000
C8···H5A	3.0800	H16A···C7^v	2.8400
C8···H1A	2.7200	H16A···C9^v	2.9800
C9···H16Aⁱⁱⁱ	2.9800	H16A···C6^v	2.9400
C9···H16Dⁱⁱⁱ	2.7900	H16A···C13^v	3.0500
C10···H16Dⁱⁱⁱ	2.8700	H16B···C10^v	2.9600
C10···H16Bⁱⁱⁱ	2.9600	H16B···C12^v	2.8600
C12···H16Dⁱⁱⁱ	2.8600	H16B···H2	2.3600
C12···H16Bⁱⁱⁱ	2.8600	H16C···H5A^v	2.5900
C13···H16Aⁱⁱⁱ	3.0500	H16D···H2	2.5400
C13···H3A	2.9000	H16D···C6^v	2.9300
C13···H16Dⁱⁱⁱ	2.8800	H16D···C7^v	2.8100
C14···H3B	2.9200	H16D···C9^v	2.7900
C14···H3A	2.7500	H16D···C10^v	2.8700
H1A···O1B	2.5700	H16D···C12^v	2.8600
H1A···H8A	2.2200	H16D···C13^v	2.8800

C2—C1—C4	89.79	C2—C3—H3A	114.00
C1—C2—C3	88.05 (19)	C2—C3—H3B	114.00
C1—C2—C15A	118.2 (5)	C4—C3—H3A	114.00
C1—C2—C15B	118.0 (9)	C4—C3—H3B	114.00
C3—C2—C15A	117.0 (6)	H3A—C3—H3B	111.00
C3—C2—C15B	116.7 (8)	C4—C5—H5A	109.00
C2—C3—C4	89.54	C4—C5—H5B	109.00
C1—C4—C3	87.59	C4—C5—H5C	109.00
C1—C4—C5	111.48	H5A—C5—H5B	109.00
C1—C4—C6	117.65	H5A—C5—H5C	109.00
C3—C4—C5	111.12	H5B—C5—H5C	109.00
C3—C4—C6	117.94	C7—C8—H8A	109.00
C5—C4—C6	109.55	C7—C8—H8B	109.00
C4—C6—C7	120.55	C7—C8—H8C	109.00
C4—C6—C13	121.94	H8A—C8—H8B	109.00
C7—C6—C13	117.5 (2)	H8A—C8—H8C	109.00
C6—C7—C8	123.3 (2)	H8B—C8—H8C	109.00
C6—C7—C9	120.0 (2)	C7—C9—H9	119.00
C8—C7—C9	116.6 (2)	C10—C9—H9	119.00
C7—C9—C10	122.8 (2)	C10—C11—H11A	109.00
C9—C10—C11	120.8 (2)	C10—C11—H11B	110.00
C9—C10—C12	116.9 (2)	C10—C11—H11C	109.00
C11—C10—C12	122.2 (3)	H11A—C11—H11B	110.00
C10—C12—C13	122.5 (2)	H11A—C11—H11C	109.00
C6—C13—C12	119.9 (2)	H11B—C11—H11C	110.00
C6—C13—C14	123.0 (2)	C10—C12—H12	119.00
C12—C13—C14	117.1 (2)	C13—C12—H12	119.00
O1A—C15A—C2	121.2 (11)	C13—C14—H14A	109.00
O1A—C15A—C16A	126.3 (12)	C13—C14—H14B	109.00
C2—C15A—C16A	112.5 (9)	C13—C14—H14C	110.00
O1B—C15B—C16B	115.3 (18)	H14A—C14—H14B	109.00
O1B—C15B—C2	125.8 (18)	H14A—C14—H14C	109.00
C2—C15B—C16B	118.8 (16)	H14B—C14—H14C	109.00
Cl1A—C16A—C15A	113.5 (8)	Cl1A—C16A—H16A	109.00
Cl1B—C16B—C15B	113.8 (13)	Cl1A—C16A—H16B	109.00
C2—C1—H1A	114.00	C15A—C16A—H16A	109.00
C2—C1—H1B	114.00	C15A—C16A—H16B	109.00
C4—C1—H1A	114.00	H16A—C16A—H16B	108.00
C4—C1—H1B	114.00	Cl1B—C16B—H16C	109.00
H1A—C1—H1B	111.00	Cl1B—C16B—H16D	109.00
C1—C2—H2	111.00	C15B—C16B—H16C	109.00
C3—C2—H2	111.00	C15B—C16B—H16D	109.00
C15A—C2—H2	111.00	H16C—C16B—H16D	108.00
C15B—C2—H2	111.00

C4—C1—C2—C3	16.79	C5—C4—C6—C13	−89.22
C4—C1—C2—C15A	136.57	C4—C6—C7—C8	−8.04
C2—C1—C4—C3	−16.94	C4—C6—C7—C9	175.15
C2—C1—C4—C5	94.83	C13—C6—C7—C8	171.0 (2)
C2—C1—C4—C6	−137.43	C13—C6—C7—C9	−5.8 (3)
C1—C2—C3—C4	−16.97	C4—C6—C13—C12	−174.95
C15A—C2—C3—C4	−137.87	C4—C6—C13—C14	7.66
C1—C2—C15A—O1A	−19.2 (16)	C7—C6—C13—C12	6.0 (3)
C1—C2—C15A—C16A	163.5 (9)	C7—C6—C13—C14	−171.4 (2)
C3—C2—C15A—O1A	84.1 (13)	C6—C7—C9—C10	1.1 (3)
C3—C2—C15A—C16A	−93.2 (11)	C8—C7—C9—C10	−175.9 (2)
C2—C3—C4—C1	16.69	C7—C9—C10—C11	−179.3 (2)
C2—C3—C4—C5	−95.43	C7—C9—C10—C12	3.4 (4)
C2—C3—C4—C6	136.91	C9—C10—C12—C13	−3.2 (4)
C1—C4—C6—C7	−38.84	C11—C10—C12—C13	179.6 (2)
C1—C4—C6—C13	142.13	C10—C12—C13—C6	−1.6 (4)
C3—C4—C6—C7	−141.79	C10—C12—C13—C14	176.0 (2)
C3—C4—C6—C13	39.18	O1A—C15A—C16A—Cl1A	4 (2)
C5—C4—C6—C7	89.81	C2—C15A—C16A—Cl1A	−178.6 (8)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, −y+3/2, z−1/2; (iii) −x+1, y−1/2, −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···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1A	0.97	2.57	2.905 (10)	100

Experimental details

Crystal data
Chemical formula	C₁₆H₂₁ClO
M_r	264.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.3808 (17), 15.236 (4), 12.472 (3)
β (°)	112.173 (15)
V (Å³)	1474.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.73 × 0.57 × 0.37

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.841, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	23037, 3378, 1993
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.195, 0.96
No. of reflections	3378
No. of parameters	197
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—C16A	1.807 (12)	O1A—C15A	1.187 (16)
Cl1B—C16B	1.68 (2)	O1B—C15B	1.22 (2)

O1A—C15A—C2	121.2 (11)	O1B—C15B—C2	125.8 (18)
O1A—C15A—C16A	126.3 (12)	Cl1A—C16A—C15A	113.5 (8)
O1B—C15B—C16B	115.3 (18)	Cl1B—C16B—C15B	113.8 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1A	0.97	2.57	2.905 (10)	100

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