N,N-Dicyclo­hexyl-2-(5,7-dichloro-8-quinol­yloxy)acetamide

Wang, J.-L.

doi:10.1107/S160053680903966X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2663

https://doi.org/10.1107/S160053680903966X

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N,N-Dicyclohexyl-2-(5,7-dichloro-8-quinolyloxy)acetamide

Jing-Lin Wang ^a ^*

^aDepartment of Biology and Chemistry, Changzhi University, Changzhi, Shanxi 046011, People's Republic of China
^*Correspondence e-mail: jlwangczu@126.com

(Received 17 August 2009; accepted 29 September 2009; online 7 October 2009)

The molecular and crystal structures of the title compound, C₂₃H₂₈Cl₂N₂O₂, are very close to those of the bromine-substituted analogue N,N-dicyclohexyl-2-(5,7-dibromo-8-quinolyloxy)acetamide. The two cyclohexyl groups adopt normal chair conformation. The amide N and C atoms have a planar configuration. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds and aromatic π⋯π stacking interactions [centroid–centroid separation = 3.5715 (4) Å for symmetry-related pyridine rings]. In addition, the crystal structure exhibits Cl⋯Cl halogen contacts of 3.4675 (3) Å.

Related literature

For background to the applications of 8-hydroxyquinoline and its derivatives, see: Bratzel et al. (1972 ); Hanna et al. (2002 ); Pierre et al. (2003 ); Tang et al. (1987 ); Zeng et al. (2006 ). For structures of 8-hydroxyquinolinate amide compounds, see: Bi et al. (2007 ); Tang et al. (2007 ); Liu et al. (2007 ).

Experimental

Crystal data

C₂₃H₂₈Cl₂N₂O₂
M_r = 435.37
Triclinic, $[P \overline 1]$
a = 9.8476 (11) Å
b = 10.7542 (12) Å
c = 11.1376 (12) Å
α = 72.392 (2)°
β = 86.880 (2)°
γ = 80.208 (2)°
V = 1107.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick,1996 ) T_min = 0.934, T_max = 0.946
5942 measured reflections
4088 independent reflections
3400 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.112
S = 1.02
4088 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2ⁱ	0.93	2.50	3.414 (3)	169
C10—H10B⋯O2ⁱⁱ	0.97	2.38	3.323 (2)	164
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+2, -z.

Data collection: APEX2 (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680903966X/bh2246sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680903966X/bh2246Isup2.hkl

checkCIF report

Comment top

8-Hydroxyquinoline and its derivatives have been used widely in analytical chemistry (Bratzel et al., 1972), coordination chemistry (Hanna et al., 2002), pharmaceutical chemistry (Pierre et al., 2003), materials chemistry (Tang et al., 1987) and many other topics. The synthesis and the development of novel 8-hydroxyquinoline derivatives have been a significant research subject (Zeng et al., 2006). Recently, the structures of 8-hydroxyquinolinate amide-type compounds, namely, N,N-diphenyl-2-(5,7-dibromoquinolin-8-yloxy)acetamide (Bi et al., 2007), N,N-diphenyl-2-(5,7-dichloroquinolin-8-yloxy)acetamide (Tang et al., 2007), and N,N-dicyclohexyl-2-(5,7-dibromoquinolin-8-yloxy)acetamide (Liu et al., 2007) have been reported. Here, we report the synthesis and crystal structure of the title compound, (I, Fig. 1), a new amide-based 5,7-dichloro-8-hydroxyquinoline derivative.

All bond lengths and angles in (I) are within normal ranges and comparable with those in the related above-cited compounds. Compound (I) has the same crystal form as the bromine analogue. The quinoline fragment is essentially planar, with a dihedral angle of 0.35 (9)° between the benzene (C1···C4/C8/C9) ring and pyridine (N1/C4···C8) ring. The two cyclohexyl groups adopt the normal chair conformation. The amide N and C atoms have a planar configuration. The crystal packing exhibits intermolecular C6—H6···O2 and C10—H10···O2 hydrogen bonds (Table 1 and Fig. 2), and π···π interactions [shortest centroid-centroid separation = 3.5715 (4) Å] between the pyridine rings of the neighbouring molecules. In addition, the crystal structure exhibits Cl···Cl halogen contacts of 3.4675 (3) Å.

Related literature top

For background to the applications of 8-hydroxyquinoline and its derivatives, see: Bratzel et al. (1972); Hanna et al. (2002); Pierre et al. (2003); Tang et al. (1987); Zeng et al. (2006). For structures of 8-hydroxyquinolinate amide compounds, see: Bi et al. (2007); Tang et al. (2007); Liu et al. (2007).

Experimental top

To a solution of 5,7-dichloro-8-hydroxyquinoline (4.18 g, 20 mmol) in acetone (60 ml) were added 2-chloro-N,N-dicyclohexylacetamide (5.16 g, 20 mmol), K₂CO₃ (3.04 g, 22 mmol) and KI (0.5 g), and the resulting mixture was refluxed for 5 h. After cooling to room temperature, the mixture was washed three times with water and filtered. The filter cake was collected and purified by recrystallization with a mixture of ethanol/water. Colourless single crystals of (I) suitable for X-ray diffraction study were obtained by slow evaporation of an ethanol solution over a period of 15 d.

Structure description top

For background to the applications of 8-hydroxyquinoline and its derivatives, see: Bratzel et al. (1972); Hanna et al. (2002); Pierre et al. (2003); Tang et al. (1987); Zeng et al. (2006). For structures of 8-hydroxyquinolinate amide compounds, see: Bi et al. (2007); Tang et al. (2007); Liu et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids.
	Fig. 2. The packing diagram of (I), viewed down the a axis, showing the intermolecular hydrogen bonds (dashed lines).

N,N-Dicyclohexyl-2-(5,7-dichloro-8-quinolyloxy)acetamide top

Crystal data top

C₂₃H₂₈Cl₂N₂O₂	Z = 2
M_r = 435.37	F(000) = 460
Triclinic, P1	D_x = 1.305 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8476 (11) Å	Cell parameters from 2570 reflections
b = 10.7542 (12) Å	θ = 2.7–25.7°
c = 11.1376 (12) Å	µ = 0.32 mm⁻¹
α = 72.392 (2)°	T = 293 K
β = 86.880 (2)°	Rhombus, colourless
γ = 80.208 (2)°	0.22 × 0.20 × 0.18 mm
V = 1107.9 (2) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	4088 independent reflections
Radiation source: fine-focus sealed tube	3400 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
φ and ω scans	θ_max = 25.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	h = −11→11
T_min = 0.934, T_max = 0.946	k = −13→10
5942 measured reflections	l = −13→11

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0584P)² + 0.3083P] where P = (F_o² + 2F_c²)/3
4088 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³
0 constraints

Crystal data top

C₂₃H₂₈Cl₂N₂O₂	γ = 80.208 (2)°
M_r = 435.37	V = 1107.9 (2) Å³
Triclinic, P1	Z = 2
a = 9.8476 (11) Å	Mo Kα radiation
b = 10.7542 (12) Å	µ = 0.32 mm⁻¹
c = 11.1376 (12) Å	T = 293 K
α = 72.392 (2)°	0.22 × 0.20 × 0.18 mm
β = 86.880 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4088 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	3400 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.946	R_int = 0.018
5942 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.02	Δρ_max = 0.33 e Å⁻³
4088 reflections	Δρ_min = −0.24 e Å⁻³
262 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.10108 (5)	0.94426 (5)	0.29221 (5)	0.03764 (15)
Cl2	−0.02741 (8)	1.39471 (7)	0.41588 (7)	0.0698 (2)
O1	0.22307 (12)	1.10728 (12)	0.06239 (11)	0.0293 (3)
O2	0.16900 (12)	0.91089 (12)	−0.08811 (12)	0.0314 (3)
N1	0.21941 (17)	1.37466 (16)	−0.00224 (16)	0.0359 (4)
N2	0.32140 (14)	1.04756 (14)	−0.18351 (13)	0.0243 (3)
C1	0.10394 (18)	1.11220 (19)	0.25299 (17)	0.0299 (4)
C2	0.04676 (19)	1.1801 (2)	0.33885 (19)	0.0373 (5)
H2A	0.0100	1.1348	0.4150	0.045*
C3	0.0459 (2)	1.3124 (2)	0.3093 (2)	0.0400 (5)
C4	0.10273 (19)	1.3853 (2)	0.19466 (19)	0.0349 (5)
C5	0.1058 (2)	1.5229 (2)	0.1581 (2)	0.0444 (5)
H5A	0.0684	1.5730	0.2105	0.053*
C6	0.1636 (2)	1.5813 (2)	0.0463 (2)	0.0473 (6)
H6A	0.1666	1.6715	0.0210	0.057*
C7	0.2187 (2)	1.5027 (2)	−0.0303 (2)	0.0439 (5)
H7A	0.2577	1.5442	−0.1067	0.053*
C8	0.16118 (18)	1.31440 (19)	0.11007 (18)	0.0301 (4)
C9	0.16069 (17)	1.17641 (18)	0.14113 (17)	0.0277 (4)
C10	0.13960 (17)	1.11664 (18)	−0.04396 (17)	0.0263 (4)
H10A	0.1299	1.2052	−0.1025	0.032*
H10B	0.0485	1.0971	−0.0158	0.032*
C11	0.21283 (17)	1.01619 (17)	−0.10754 (16)	0.0249 (4)
C12	0.38451 (17)	0.96001 (17)	−0.25850 (16)	0.0246 (4)
H12A	0.4570	1.0035	−0.3095	0.030*
C13	0.45558 (18)	0.82518 (18)	−0.17828 (17)	0.0284 (4)
H13A	0.3882	0.7785	−0.1242	0.034*
H13B	0.5241	0.8370	−0.1251	0.034*
C14	0.5251 (2)	0.7433 (2)	−0.26245 (19)	0.0364 (5)
H14A	0.5999	0.7849	−0.3089	0.044*
H14B	0.5638	0.6558	−0.2102	0.044*
C15	0.4236 (2)	0.73116 (19)	−0.35466 (19)	0.0360 (5)
H15A	0.3540	0.6814	−0.3084	0.043*
H15B	0.4718	0.6829	−0.4093	0.043*
C16	0.3540 (2)	0.8660 (2)	−0.43435 (18)	0.0351 (4)
H16A	0.2867	0.8548	−0.4891	0.042*
H16B	0.4223	0.9126	−0.4869	0.042*
C17	0.28254 (19)	0.94781 (19)	−0.35147 (17)	0.0322 (4)
H17A	0.2076	0.9060	−0.3054	0.039*
H17B	0.2439	1.0352	−0.4040	0.039*
C18	0.37854 (17)	1.17059 (17)	−0.19956 (16)	0.0246 (4)
H18A	0.3305	1.2136	−0.1397	0.029*
C19	0.35073 (19)	1.26735 (18)	−0.33206 (17)	0.0303 (4)
H19A	0.3936	1.2264	−0.3942	0.036*
H19B	0.2523	1.2884	−0.3475	0.036*
C20	0.4082 (2)	1.39395 (19)	−0.34509 (19)	0.0364 (5)
H20A	0.3579	1.4397	−0.2893	0.044*
H20B	0.3948	1.4516	−0.4308	0.044*
C21	0.5614 (2)	1.36517 (19)	−0.31312 (19)	0.0364 (5)
H21A	0.6130	1.3274	−0.3739	0.044*
H21B	0.5934	1.4470	−0.3181	0.044*
C22	0.5870 (2)	1.26914 (19)	−0.18086 (18)	0.0336 (4)
H22A	0.6851	1.2489	−0.1638	0.040*
H22B	0.5422	1.3102	−0.1195	0.040*
C23	0.53174 (18)	1.14179 (18)	−0.16782 (17)	0.0290 (4)
H23A	0.5456	1.0840	−0.0822	0.035*
H23B	0.5822	1.0967	−0.2240	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0375 (3)	0.0326 (3)	0.0393 (3)	−0.0063 (2)	−0.0005 (2)	−0.0051 (2)
Cl2	0.0808 (5)	0.0768 (5)	0.0705 (4)	−0.0121 (4)	0.0222 (4)	−0.0538 (4)
O1	0.0266 (6)	0.0312 (7)	0.0302 (7)	0.0007 (5)	−0.0003 (5)	−0.0123 (5)
O2	0.0284 (7)	0.0265 (7)	0.0431 (8)	−0.0122 (5)	0.0090 (6)	−0.0135 (6)
N1	0.0348 (9)	0.0320 (9)	0.0406 (9)	−0.0091 (7)	−0.0001 (7)	−0.0084 (7)
N2	0.0248 (7)	0.0204 (8)	0.0297 (8)	−0.0077 (6)	0.0051 (6)	−0.0090 (6)
C1	0.0253 (9)	0.0323 (10)	0.0330 (10)	−0.0056 (7)	−0.0024 (7)	−0.0103 (8)
C2	0.0320 (10)	0.0505 (13)	0.0334 (10)	−0.0103 (9)	0.0040 (8)	−0.0170 (9)
C3	0.0349 (10)	0.0507 (14)	0.0439 (12)	−0.0047 (9)	0.0025 (9)	−0.0299 (10)
C4	0.0282 (10)	0.0358 (11)	0.0457 (12)	−0.0021 (8)	−0.0051 (8)	−0.0205 (9)
C5	0.0383 (11)	0.0362 (12)	0.0661 (15)	−0.0001 (9)	−0.0099 (10)	−0.0275 (11)
C6	0.0449 (12)	0.0289 (11)	0.0694 (16)	−0.0073 (9)	−0.0133 (11)	−0.0136 (11)
C7	0.0446 (12)	0.0353 (12)	0.0507 (13)	−0.0144 (9)	−0.0026 (10)	−0.0065 (10)
C8	0.0226 (9)	0.0312 (10)	0.0376 (10)	−0.0035 (7)	−0.0044 (8)	−0.0115 (8)
C9	0.0209 (8)	0.0324 (10)	0.0314 (9)	−0.0018 (7)	−0.0020 (7)	−0.0128 (8)
C10	0.0218 (8)	0.0265 (10)	0.0315 (9)	−0.0054 (7)	0.0019 (7)	−0.0094 (7)
C11	0.0213 (8)	0.0244 (10)	0.0287 (9)	−0.0050 (7)	−0.0012 (7)	−0.0066 (7)
C12	0.0242 (9)	0.0239 (9)	0.0290 (9)	−0.0092 (7)	0.0057 (7)	−0.0108 (7)
C13	0.0286 (9)	0.0278 (10)	0.0301 (9)	−0.0047 (7)	−0.0024 (7)	−0.0103 (8)
C14	0.0357 (10)	0.0316 (11)	0.0418 (11)	0.0012 (8)	−0.0016 (9)	−0.0139 (9)
C15	0.0465 (11)	0.0297 (11)	0.0371 (11)	−0.0106 (9)	0.0046 (9)	−0.0163 (9)
C16	0.0421 (11)	0.0367 (11)	0.0306 (10)	−0.0092 (9)	−0.0026 (8)	−0.0140 (8)
C17	0.0322 (10)	0.0329 (11)	0.0321 (10)	−0.0030 (8)	−0.0050 (8)	−0.0109 (8)
C18	0.0250 (9)	0.0209 (9)	0.0291 (9)	−0.0074 (7)	0.0046 (7)	−0.0082 (7)
C19	0.0298 (9)	0.0258 (10)	0.0340 (10)	−0.0071 (7)	−0.0012 (8)	−0.0053 (8)
C20	0.0455 (12)	0.0231 (10)	0.0362 (11)	−0.0087 (8)	0.0017 (9)	−0.0009 (8)
C21	0.0440 (11)	0.0293 (11)	0.0392 (11)	−0.0203 (9)	0.0064 (9)	−0.0086 (8)
C22	0.0355 (10)	0.0313 (11)	0.0376 (11)	−0.0150 (8)	0.0001 (8)	−0.0104 (8)
C23	0.0294 (9)	0.0252 (10)	0.0315 (9)	−0.0093 (7)	−0.0017 (8)	−0.0045 (8)

Geometric parameters (Å, º) top

Cl1—C1	1.730 (2)	C13—H13A	0.9700
Cl2—C3	1.743 (2)	C13—H13B	0.9700
O1—C9	1.371 (2)	C14—C15	1.519 (3)
O1—C10	1.447 (2)	C14—H14A	0.9700
O2—C11	1.234 (2)	C14—H14B	0.9700
N1—C7	1.315 (3)	C15—C16	1.520 (3)
N1—C8	1.368 (2)	C15—H15A	0.9700
N2—C11	1.351 (2)	C15—H15B	0.9700
N2—C12	1.480 (2)	C16—C17	1.527 (3)
N2—C18	1.483 (2)	C16—H16A	0.9700
C1—C9	1.370 (3)	C16—H16B	0.9700
C1—C2	1.410 (3)	C17—H17A	0.9700
C2—C3	1.358 (3)	C17—H17B	0.9700
C2—H2A	0.9300	C18—C23	1.526 (2)
C3—C4	1.422 (3)	C18—C19	1.534 (2)
C4—C5	1.416 (3)	C18—H18A	0.9800
C4—C8	1.424 (3)	C19—C20	1.526 (3)
C5—C6	1.357 (3)	C19—H19A	0.9700
C5—H5A	0.9300	C19—H19B	0.9700
C6—C7	1.402 (3)	C20—C21	1.527 (3)
C6—H6A	0.9300	C20—H20A	0.9700
C7—H7A	0.9300	C20—H20B	0.9700
C8—C9	1.419 (3)	C21—C22	1.527 (3)
C10—C11	1.527 (2)	C21—H21A	0.9700
C10—H10A	0.9700	C21—H21B	0.9700
C10—H10B	0.9700	C22—C23	1.522 (2)
C12—C13	1.526 (2)	C22—H22A	0.9700
C12—C17	1.529 (2)	C22—H22B	0.9700
C12—H12A	0.9800	C23—H23A	0.9700
C13—C14	1.532 (3)	C23—H23B	0.9700

C9—O1—C10	114.18 (13)	C13—C14—H14B	109.3
C7—N1—C8	117.15 (18)	H14A—C14—H14B	108.0
C11—N2—C12	119.90 (14)	C14—C15—C16	111.50 (16)
C11—N2—C18	122.60 (14)	C14—C15—H15A	109.3
C12—N2—C18	117.46 (13)	C16—C15—H15A	109.3
C9—C1—C2	121.40 (18)	C14—C15—H15B	109.3
C9—C1—Cl1	120.29 (15)	C16—C15—H15B	109.3
C2—C1—Cl1	118.31 (15)	H15A—C15—H15B	108.0
C3—C2—C1	119.38 (18)	C15—C16—C17	110.99 (15)
C3—C2—H2A	120.3	C15—C16—H16A	109.4
C1—C2—H2A	120.3	C17—C16—H16A	109.4
C2—C3—C4	122.17 (18)	C15—C16—H16B	109.4
C2—C3—Cl2	118.59 (16)	C17—C16—H16B	109.4
C4—C3—Cl2	119.24 (16)	H16A—C16—H16B	108.0
C5—C4—C3	125.15 (19)	C16—C17—C12	110.61 (15)
C5—C4—C8	117.42 (19)	C16—C17—H17A	109.5
C3—C4—C8	117.43 (18)	C12—C17—H17A	109.5
C6—C5—C4	119.7 (2)	C16—C17—H17B	109.5
C6—C5—H5A	120.2	C12—C17—H17B	109.5
C4—C5—H5A	120.2	H17A—C17—H17B	108.1
C5—C6—C7	118.6 (2)	N2—C18—C23	111.79 (14)
C5—C6—H6A	120.7	N2—C18—C19	111.53 (14)
C7—C6—H6A	120.7	C23—C18—C19	111.35 (14)
N1—C7—C6	125.0 (2)	N2—C18—H18A	107.3
N1—C7—H7A	117.5	C23—C18—H18A	107.3
C6—C7—H7A	117.5	C19—C18—H18A	107.3
N1—C8—C9	117.69 (17)	C20—C19—C18	110.40 (15)
N1—C8—C4	122.22 (18)	C20—C19—H19A	109.6
C9—C8—C4	120.09 (17)	C18—C19—H19A	109.6
C1—C9—O1	120.48 (17)	C20—C19—H19B	109.6
C1—C9—C8	119.52 (17)	C18—C19—H19B	109.6
O1—C9—C8	119.92 (16)	H19A—C19—H19B	108.1
O1—C10—C11	107.15 (13)	C19—C20—C21	111.63 (16)
O1—C10—H10A	110.3	C19—C20—H20A	109.3
C11—C10—H10A	110.3	C21—C20—H20A	109.3
O1—C10—H10B	110.3	C19—C20—H20B	109.3
C11—C10—H10B	110.3	C21—C20—H20B	109.3
H10A—C10—H10B	108.5	H20A—C20—H20B	108.0
O2—C11—N2	123.20 (16)	C22—C21—C20	110.66 (16)
O2—C11—C10	118.40 (15)	C22—C21—H21A	109.5
N2—C11—C10	118.39 (15)	C20—C21—H21A	109.5
N2—C12—C13	113.45 (14)	C22—C21—H21B	109.5
N2—C12—C17	112.06 (14)	C20—C21—H21B	109.5
C13—C12—C17	112.03 (15)	H21A—C21—H21B	108.1
N2—C12—H12A	106.2	C23—C22—C21	110.94 (16)
C13—C12—H12A	106.2	C23—C22—H22A	109.5
C17—C12—H12A	106.2	C21—C22—H22A	109.5
C12—C13—C14	110.40 (15)	C23—C22—H22B	109.5
C12—C13—H13A	109.6	C21—C22—H22B	109.5
C14—C13—H13A	109.6	H22A—C22—H22B	108.0
C12—C13—H13B	109.6	C22—C23—C18	110.84 (15)
C14—C13—H13B	109.6	C22—C23—H23A	109.5
H13A—C13—H13B	108.1	C18—C23—H23A	109.5
C15—C14—C13	111.47 (16)	C22—C23—H23B	109.5
C15—C14—H14A	109.3	C18—C23—H23B	109.5
C13—C14—H14A	109.3	H23A—C23—H23B	108.1
C15—C14—H14B	109.3

C9—C1—C2—C3	1.0 (3)	C12—N2—C11—O2	6.4 (2)
Cl1—C1—C2—C3	−179.00 (15)	C18—N2—C11—O2	−175.96 (16)
C1—C2—C3—C4	−0.9 (3)	C12—N2—C11—C10	−172.74 (14)
C1—C2—C3—Cl2	179.13 (15)	C18—N2—C11—C10	4.9 (2)
C2—C3—C4—C5	−179.75 (19)	O1—C10—C11—O2	102.13 (17)
Cl2—C3—C4—C5	0.2 (3)	O1—C10—C11—N2	−78.66 (18)
C2—C3—C4—C8	0.2 (3)	C11—N2—C12—C13	−66.8 (2)
Cl2—C3—C4—C8	−179.80 (14)	C18—N2—C12—C13	115.52 (16)
C3—C4—C5—C6	179.7 (2)	C11—N2—C12—C17	61.3 (2)
C8—C4—C5—C6	−0.3 (3)	C18—N2—C12—C17	−116.39 (16)
C4—C5—C6—C7	0.1 (3)	N2—C12—C13—C14	−176.85 (14)
C8—N1—C7—C6	0.3 (3)	C17—C12—C13—C14	55.0 (2)
C5—C6—C7—N1	−0.2 (3)	C12—C13—C14—C15	−54.8 (2)
C7—N1—C8—C9	179.69 (17)	C13—C14—C15—C16	56.0 (2)
C7—N1—C8—C4	−0.5 (3)	C14—C15—C16—C17	−56.3 (2)
C5—C4—C8—N1	0.4 (3)	C15—C16—C17—C12	55.7 (2)
C3—C4—C8—N1	−179.53 (17)	N2—C12—C17—C16	175.45 (14)
C5—C4—C8—C9	−179.73 (17)	C13—C12—C17—C16	−55.7 (2)
C3—C4—C8—C9	0.3 (3)	C11—N2—C18—C23	123.66 (17)
C2—C1—C9—O1	176.09 (16)	C12—N2—C18—C23	−58.69 (19)
Cl1—C1—C9—O1	−3.9 (2)	C11—N2—C18—C19	−110.94 (18)
C2—C1—C9—C8	−0.5 (3)	C12—N2—C18—C19	66.71 (19)
Cl1—C1—C9—C8	179.51 (13)	N2—C18—C19—C20	178.92 (14)
C10—O1—C9—C1	101.90 (19)	C23—C18—C19—C20	−55.4 (2)
C10—O1—C9—C8	−81.49 (19)	C18—C19—C20—C21	55.5 (2)
N1—C8—C9—C1	179.70 (16)	C19—C20—C21—C22	−56.2 (2)
C4—C8—C9—C1	−0.1 (3)	C20—C21—C22—C23	56.5 (2)
N1—C8—C9—O1	3.1 (2)	C21—C22—C23—C18	−56.7 (2)
C4—C8—C9—O1	−176.79 (15)	N2—C18—C23—C22	−178.16 (14)
C9—O1—C10—C11	−170.23 (14)	C19—C18—C23—C22	56.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2ⁱ	0.93	2.50	3.414 (3)	169
C10—H10B···O2ⁱⁱ	0.97	2.38	3.323 (2)	164

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₈Cl₂N₂O₂
M_r	435.37
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.8476 (11), 10.7542 (12), 11.1376 (12)
α, β, γ (°)	72.392 (2), 86.880 (2), 80.208 (2)
V (Å³)	1107.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick,1996)
T_min, T_max	0.934, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	5942, 4088, 3400
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.112, 1.02
No. of reflections	4088
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.24

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2ⁱ	0.93	2.50	3.414 (3)	169.1
C10—H10B···O2ⁱⁱ	0.97	2.38	3.323 (2)	163.8

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, −z.

References

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