4,4′-Dichloro-2,2′-(piperazine-1,4-diyldimethyl­ene)diphenol

Kubono, K.; Tsuno, Y.; Tani, K.; Yokoi, K.

doi:10.1107/S1600536808035769

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2309

doi:10.1107/S1600536808035769

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4,4′-Dichloro-2,2′-(piperazine-1,4-diyldimethylene)diphenol

Koji Kubono,^a ^* Yuki Tsuno,^a Keita Tani ^a and Kunihiko Yokoi ^a

^aDivision of Natural Sciences, Osaka Kyoiku University, Kashiwara, Osaka 582-8582, Japan
^*Correspondence e-mail: kubono@cc.osaka-kyoiku.ac.jp

(Received 15 October 2008; accepted 31 October 2008; online 13 November 2008)

In the titile compound, C₁₈H₂₀Cl₂N₂O₂, the piperazine ring adopts a chair conformation. The molecule has a non-crystallographic inversion centre in the middle of the piperazine ring at approximate position (3/4, 1/8, 3/8). There are intramolecular O—H⋯N hydrogen bonds forming S(6) ring motifs. Intermolecular C—H⋯O hydrogen bonds generate antiparallel C(5) chain motifs propagating along the b axis, forming sheets parallel to the bc plane with a first-level graph-set S(6)C(5)R₆⁶(26).

Related literature

For graph-set notations for hydrogen bonds, see: Bernstein et al. (1995 ). For the synthesis of a ligand with two piperazine arms, see: Bharathi et al. (2006 ). For the use of piperazine derivatives as buffers, see: Good et al. (1966 ). For the monoclinic and orthorhombic polymorphs of a tetrachloro-2,2′-(piperazine-1,4-diyldimethylene)diphenol, see: Kubono & Yokoi (2007 ). For the structure of 1,4-bis(2-hydroxy-5-methylbenzyl)piperazine, see: Kuppayee et al. (1999 ).

Experimental

Crystal data

C₁₈H₂₀Cl₂N₂O₂
M_r = 367.26
Orthorhombic, P b c a
a = 14.055 (4) Å
b = 21.214 (11) Å
c = 11.873 (3) Å
V = 3540 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 298.1 K
0.18 × 0.13 × 0.13 mm

Data collection

Rigaku AFC-7R diffractometer
Absorption correction: none
5928 measured reflections
4066 independent reflections
2735 reflections with F² > 2σ(F²)
R_int = 0.039
3 standard reflections every 150 reflections intensity decay: 0.7%

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.105
S = 1.00
2739 reflections
237 parameters
All H-atom parameters refined
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.85	1.88	2.649 (3)	150
O2—H20⋯N2	0.85	1.87	2.647 (3)	151
C7—H6⋯O2ⁱ	0.95	2.59	3.230 (3)	125
C12—H15⋯O1ⁱⁱ	0.95	2.56	3.300 (3)	134
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ .

Data collection: WinAFC (Rigaku/MSC, 2006 ); cell refinement: WinAFC; data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035769/si2120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035769/si2120Isup2.hkl

checkCIF report

Comment top

Piprazine derivatives are widly utilized as buffers, e.g., 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES) (Good et al., 1966), and can act as complexing reagents with metal ions (Bharathi et al., 2006).

The molecular structure of the title compound (Fig. 1) (I), consists of two chlorophenol arms and a piperazine ring, which adopt a chair conformation. The molecule has a pseudo-inversion centre in the middle of the piperazine ring at position (3/4, 1/8, 3/8). It is interesting to note that in the polymorh structures of dichlorophenol derivatives (Kubono & Yokoi, 2007) the molecules occupy crystallographic inversion centres (Z' = 1/2). The bond lengths and angles in (I) are normal and comparable with those in the monoclinic and orthorhombic polymorph structures (Kubono & Yokoi, 2007) and in the p-cresol derivative (Kuppayee et al., 1999). Intramolecular O—H···N hydrogen bonds in (I) have similar geometric parameters and higher level graph set notations as was observed in the polymorph structures. The torsion angles C1—C6—C7—N1 and N2—C12—C13—C18 are -34.8 (3) and 37.5 (3) °, respectively. The dihedral angles between the mean planes of two benzene rings are 4.68 (12) °.

In the crystal structure of (I), there are two intermolecular C—H···O hydrogen bonds (Table 1). Atom C7 in the molecule at (x, y, z) acts as hydrogen bond donor to atom O2 in the molecule at (x, 1/2 - y, z - 1/2), so forming a C(5) (Bernstein et al., 1995) chain running parallel to the [010] direction and generated by the c-glide plane at y = 1/4. In addition, atom C12 in the molecule at (x, y, z) acts as hydrogen bond donor to atom O1 atom in the molecule at (3/2 - x, -y, 1/2 + z), so forming a C(5) chain running parallel to the [010] direction and generated by the 2₁ screw axis along (3/4, 0, z). The molecules are linked by the combination of the two S(6) rings and the two antiparalle C(5) chains into a sheet parallel to b,c-plane with a first level graph set S(6)C(5)R₆⁶(26) (Fig. 2).

Related literature top

For graph-set notations for hydrogen bonds, see: Bernstein et al. (1995). For the synthesis of a ligand with two piperazine arms, see: Bharathi et al. (2006). For the use of piperazine derivatives as buffers, see: Good et al. (1966). For the monoclinic and orthorhombic polymorphs of a tetrachloro-2,2'(piperazine-1,4-diyldimethylene)-diphenol, see: Kubono & Yokoi (2007). For the structure of 1,4-bis(2-hydroxy-5-methylbenzyl)-piperazine, see: Kuppayee et al. (1999).

Experimental top

A mixture of 4-chlorophenol (25.0 g, 194 mmol), piperazine (8.34 g, 97.2 mmol) and paraformaldehyde (5.82 g, 194 mmol) in methanol (80 ml) was refluxed for 6 h. The mixture was cooled to room temperature, then the solvent was evaporated under vacuum. The product was recrystallized from CHCl₃—MeOH to give prismatic crystals of (I) [yeild 13.8 g (38.7%); m.p. 515.0–515.4 K]. Analysis calculated for C₁₈H₂₀Cl₄N₂O₂: C 58.86, H 5.49, N 7.63%; found: C 58.50, H 5.44, N 7.55%. ¹H-NMR(CDCl₃, p.p.m., 400 MHz): 2.68 (brs, 8H, CH₂), 3.69 (s, 4H, CH₂), 6.75 (d, J = 2.4 Hz, 2H, ArH), 6.96 (s, 2H, ArH), 7.13 (d, J = 2.4 Hz, 2H, ArH), 10.6 (brs, 2H, OH).

Computing details top

Data collection: WinAFC (Rigaku/MSC, 2006); cell refinement: WinAFC (Rigaku/MSC, 2006); data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006).

Figures top

	Fig. 1. The molecular structure of (I) with the atom-labelling scheme and displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
	Fig. 2. The molecular packing of (I), showing the formation of a sheet with a first level graph set S(6)C(5)R₆⁶(26). The hydrogen bonds are shown as dashed lines. The H atoms not involved in the hydrogen bonds have been omitted for clarity.

4,4'-Dichloro-2,2'-(piperazine-1,4-diyldimethylene)diphenol top

Crystal data top

C₁₈H₂₀Cl₂N₂O₂	F(000) = 1536.00
M_r = 367.26	D_x = 1.378 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 18 reflections
a = 14.055 (4) Å	θ = 13.7–16.9°
b = 21.214 (11) Å	µ = 0.38 mm⁻¹
c = 11.873 (3) Å	T = 298 K
V = 3540 (2) Å³	Prismatic, colorless
Z = 8	0.18 × 0.13 × 0.13 mm

Data collection top

Rigaku AFC-7R diffractometer	θ_max = 27.5°
ω scans	h = −10→18
5928 measured reflections	k = 0→27
4066 independent reflections	l = −8→15
2735 reflections with F² > 2σ(F²)	3 standard reflections every 150 reflections
R_int = 0.039	intensity decay: 0.7%

Refinement top

Refinement on F²	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.039	w = 1/[0.0011F_o² + σ(F_o²)]/(4F_o²)
wR(F²) = 0.105	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.33 e Å⁻³
2739 reflections	Δρ_min = −0.45 e Å⁻³
237 parameters

Crystal data top

C₁₈H₂₀Cl₂N₂O₂	V = 3540 (2) Å³
M_r = 367.26	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.055 (4) Å	µ = 0.38 mm⁻¹
b = 21.214 (11) Å	T = 298 K
c = 11.873 (3) Å	0.18 × 0.13 × 0.13 mm

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.039
5928 measured reflections	3 standard reflections every 150 reflections
4066 independent reflections	intensity decay: 0.7%
2735 reflections with F² > 2σ(F²)

Refinement top

R[F² > 2σ(F²)] = 0.039	237 parameters
wR(F²) = 0.105	All H-atom parameters refined
S = 1.00	Δρ_max = 0.33 e Å⁻³
2739 reflections	Δρ_min = −0.45 e Å⁻³

Special details top

Geometry. The molecule adopts a non-crystallographic inversion centre in the middle of the piperazine ring at an approximate position (3/4, 1/8, 3/8).

Refinement. Refinement was performed using reflections with F² > 2.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
Cl1	0.43588 (6)	0.27754 (4)	−0.07209 (8)	0.0807 (3)
Cl2	1.07341 (7)	−0.01127 (5)	0.83011 (9)	0.0914 (4)
O1	0.75085 (15)	0.11534 (9)	0.07111 (17)	0.0559 (7)
O2	0.74244 (15)	0.13266 (9)	0.67705 (18)	0.0643 (8)
N1	0.73683 (16)	0.16416 (11)	0.2758 (2)	0.0385 (7)
N2	0.77032 (17)	0.08768 (10)	0.4717 (2)	0.0385 (8)
C1	0.6764 (2)	0.15283 (15)	0.0418 (2)	0.0435 (10)
C2	0.6298 (2)	0.14079 (15)	−0.0579 (2)	0.0506 (11)
C3	0.5560 (2)	0.17790 (18)	−0.0936 (2)	0.0558 (12)
C4	0.5283 (2)	0.22809 (16)	−0.0274 (3)	0.0526 (12)
C5	0.5720 (2)	0.24037 (15)	0.0734 (2)	0.0477 (11)
C6	0.6466 (2)	0.20327 (14)	0.1097 (2)	0.0398 (10)
C7	0.6988 (2)	0.21952 (13)	0.2166 (2)	0.0459 (10)
C8	0.8043 (2)	0.18345 (14)	0.3642 (2)	0.0483 (10)
C9	0.8455 (2)	0.12615 (13)	0.4217 (2)	0.0465 (10)
C10	0.7022 (2)	0.06864 (13)	0.3845 (2)	0.0451 (10)
C11	0.6609 (2)	0.12632 (13)	0.3279 (2)	0.0466 (10)
C12	0.8101 (2)	0.03329 (13)	0.5321 (2)	0.0476 (10)
C13	0.8583 (2)	0.05200 (14)	0.6408 (2)	0.0381 (10)
C14	0.9375 (2)	0.01930 (13)	0.6786 (2)	0.0451 (11)
C15	0.9773 (2)	0.03340 (15)	0.7820 (3)	0.0505 (11)
C16	0.9415 (2)	0.08039 (17)	0.8475 (2)	0.0544 (12)
C17	0.8640 (2)	0.11345 (15)	0.8107 (3)	0.0563 (12)
C18	0.8214 (2)	0.09977 (14)	0.7088 (2)	0.0432 (11)
H1	0.7660	0.1247	0.1381	0.067*
H2	0.6488	0.1057	−0.1022	0.061*
H3	0.5249	0.1702	−0.1632	0.067*
H4	0.5506	0.2748	0.1178	0.057*
H5	0.6569	0.2415	0.2656	0.055*
H6	0.7510	0.2460	0.1977	0.055*
H7	0.8537	0.2074	0.3303	0.058*
H8	0.7724	0.2085	0.4187	0.058*
H9	0.8880	0.1390	0.4795	0.056*
H10	0.8790	0.1019	0.3674	0.056*
H11	0.7338	0.0442	0.3288	0.054*
H12	0.6530	0.0443	0.4178	0.054*
H13	0.6301	0.1509	0.3839	0.056*
H14	0.6161	0.1145	0.2718	0.056*
H15	0.7599	0.0047	0.5485	0.057*
H16	0.8557	0.0132	0.4853	0.057*
H17	0.9651	−0.0127	0.6331	0.054*
H18	0.9701	0.0897	0.9181	0.065*
H19	0.8387	0.1466	0.8555	0.068*
H20	0.7346	0.1261	0.6069	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0581 (6)	0.0946 (8)	0.0893 (8)	0.0015 (5)	−0.0153 (6)	0.0291 (5)
Cl2	0.0782 (7)	0.1153 (8)	0.0806 (8)	0.0288 (6)	−0.0241 (6)	−0.0050 (6)
O1	0.0720 (15)	0.0498 (13)	0.0459 (15)	0.0121 (12)	−0.0003 (12)	−0.0089 (12)
O2	0.0803 (17)	0.0591 (14)	0.0534 (17)	0.0224 (13)	−0.0010 (13)	−0.0097 (12)
N1	0.0419 (15)	0.0361 (14)	0.0377 (17)	−0.0053 (13)	−0.0039 (13)	0.0012 (13)
N2	0.0441 (16)	0.0304 (14)	0.0410 (17)	−0.0081 (13)	−0.0031 (13)	0.0035 (13)
C1	0.049 (2)	0.041 (2)	0.040 (2)	−0.0044 (18)	0.0014 (18)	0.0048 (18)
C2	0.064 (2)	0.050 (2)	0.037 (2)	−0.014 (2)	0.005 (2)	0.0001 (19)
C3	0.059 (2)	0.067 (2)	0.041 (2)	−0.025 (2)	−0.008 (2)	0.007 (2)
C4	0.043 (2)	0.058 (2)	0.057 (2)	−0.0100 (19)	−0.004 (2)	0.018 (2)
C5	0.045 (2)	0.047 (2)	0.051 (2)	−0.0007 (18)	0.002 (2)	0.0018 (18)
C6	0.049 (2)	0.040 (2)	0.031 (2)	−0.0032 (17)	0.0062 (17)	−0.0026 (17)
C7	0.058 (2)	0.0411 (19)	0.039 (2)	0.0042 (17)	0.0026 (18)	−0.0027 (16)
C8	0.059 (2)	0.044 (2)	0.041 (2)	−0.0142 (18)	−0.0025 (18)	−0.0003 (17)
C9	0.050 (2)	0.045 (2)	0.045 (2)	−0.0105 (18)	−0.0053 (17)	−0.0001 (18)
C10	0.046 (2)	0.039 (2)	0.050 (2)	−0.0127 (16)	−0.0053 (18)	0.0023 (16)
C11	0.045 (2)	0.051 (2)	0.044 (2)	−0.0080 (17)	−0.0043 (16)	−0.0036 (17)
C12	0.058 (2)	0.0357 (19)	0.049 (2)	−0.0029 (16)	0.0037 (18)	−0.0009 (16)
C13	0.049 (2)	0.0341 (19)	0.031 (2)	−0.0020 (17)	0.0026 (17)	0.0038 (16)
C14	0.052 (2)	0.040 (2)	0.043 (2)	0.0028 (18)	0.011 (2)	−0.0008 (17)
C15	0.050 (2)	0.054 (2)	0.048 (2)	0.0009 (18)	−0.002 (2)	0.0006 (19)
C16	0.060 (2)	0.064 (2)	0.039 (2)	−0.007 (2)	−0.0029 (19)	0.0019 (19)
C17	0.077 (2)	0.053 (2)	0.039 (2)	0.000 (2)	0.011 (2)	−0.010 (2)
C18	0.054 (2)	0.0357 (19)	0.040 (2)	0.0063 (17)	0.0106 (19)	0.0029 (17)

Geometric parameters (Å, º) top

Cl1—C4	1.751 (3)	C15—C16	1.361 (4)
Cl2—C15	1.746 (3)	C16—C17	1.367 (5)
O1—C1	1.359 (3)	C17—C18	1.381 (4)
O2—C18	1.364 (3)	O1—H1	0.848
N1—C7	1.469 (3)	O2—H20	0.852
N1—C8	1.472 (3)	C2—H2	0.950
N1—C11	1.472 (3)	C3—H3	0.950
N2—C9	1.461 (3)	C5—H4	0.950
N2—C10	1.467 (3)	C7—H5	0.950
N2—C12	1.469 (3)	C7—H6	0.950
C1—C2	1.377 (4)	C8—H7	0.950
C1—C6	1.404 (4)	C8—H8	0.950
C2—C3	1.369 (4)	C9—H9	0.950
C3—C4	1.380 (5)	C9—H10	0.950
C4—C5	1.371 (5)	C10—H11	0.950
C5—C6	1.380 (4)	C10—H12	0.950
C6—C7	1.507 (4)	C11—H13	0.950
C8—C9	1.509 (4)	C11—H14	0.950
C10—C11	1.512 (3)	C12—H15	0.950
C12—C13	1.510 (4)	C12—H16	0.950
C13—C14	1.386 (4)	C14—H17	0.950
C13—C18	1.395 (4)	C16—H18	0.950
C14—C15	1.383 (4)	C17—H19	0.950

C7—N1—C8	110.6 (2)	C2—C3—H3	121.3
C7—N1—C11	111.9 (2)	C4—C3—H3	119.9
C8—N1—C11	108.6 (2)	C4—C5—H4	119.2
C9—N2—C10	109.8 (2)	C6—C5—H4	120.4
C9—N2—C12	111.2 (2)	N1—C7—H5	109.0
C10—N2—C12	112.1 (2)	N1—C7—H6	107.8
O1—C1—C2	118.5 (2)	C6—C7—H5	109.0
O1—C1—C6	121.9 (2)	C6—C7—H6	108.1
C2—C1—C6	119.5 (3)	H5—C7—H6	109.5
C1—C2—C3	121.3 (3)	N1—C8—H7	108.5
C2—C3—C4	118.8 (3)	N1—C8—H8	109.8
Cl1—C4—C3	120.0 (2)	C9—C8—H7	110.0
Cl1—C4—C5	118.9 (2)	C9—C8—H8	108.9
C3—C4—C5	121.1 (3)	H7—C8—H8	109.5
C4—C5—C6	120.3 (3)	N2—C9—H9	108.7
C1—C6—C5	118.8 (2)	N2—C9—H10	109.4
C1—C6—C7	120.9 (2)	C8—C9—H9	109.7
C5—C6—C7	120.2 (2)	C8—C9—H10	108.7
N1—C7—C6	113.4 (2)	H9—C9—H10	109.5
N1—C8—C9	110.2 (2)	N2—C10—H11	109.6
N2—C9—C8	110.9 (2)	N2—C10—H12	109.3
N2—C10—C11	110.0 (2)	C11—C10—H11	108.2
N1—C11—C10	110.5 (2)	C11—C10—H12	110.3
N2—C12—C13	112.4 (2)	H11—C10—H12	109.5
C12—C13—C14	120.3 (2)	N1—C11—H13	109.0
C12—C13—C18	121.3 (2)	N1—C11—H14	109.3
C14—C13—C18	118.3 (2)	C10—C11—H13	108.0
C13—C14—C15	120.3 (2)	C10—C11—H14	110.6
Cl2—C15—C14	119.1 (2)	H13—C11—H14	109.5
Cl2—C15—C16	119.8 (2)	N2—C12—H15	108.6
C14—C15—C16	121.0 (3)	N2—C12—H16	108.9
C15—C16—C17	119.3 (3)	C13—C12—H15	109.0
C16—C17—C18	121.1 (3)	C13—C12—H16	108.4
O2—C18—C13	120.9 (2)	H15—C12—H16	109.5
O2—C18—C17	119.1 (2)	C13—C14—H17	120.1
C13—C18—C17	119.9 (3)	C15—C14—H17	119.6
C1—O1—H1	107.2	C15—C16—H18	119.9
C18—O2—H20	107.0	C17—C16—H18	120.8
C1—C2—H2	119.1	C16—C17—H19	119.9
C3—C2—H2	119.5	C18—C17—H19	118.9

C7—N1—C8—C9	−178.0 (2)	C3—C4—C5—C6	1.4 (5)
C8—N1—C7—C6	167.4 (2)	C4—C5—C6—C1	−0.2 (4)
C7—N1—C11—C10	178.1 (2)	C4—C5—C6—C7	175.9 (2)
C11—N1—C7—C6	−71.4 (3)	C1—C6—C7—N1	−34.8 (3)
C8—N1—C11—C10	−59.5 (2)	C5—C6—C7—N1	149.3 (2)
C11—N1—C8—C9	58.7 (2)	N1—C8—C9—N2	−58.8 (3)
C9—N2—C10—C11	−57.8 (2)	N2—C10—C11—N1	59.6 (2)
C10—N2—C9—C8	57.8 (2)	N2—C12—C13—C14	−146.3 (2)
C9—N2—C12—C13	72.3 (3)	N2—C12—C13—C18	37.5 (3)
C12—N2—C9—C8	−177.5 (2)	C12—C13—C14—C15	−175.2 (2)
C10—N2—C12—C13	−164.3 (2)	C12—C13—C18—O2	−2.4 (4)
C12—N2—C10—C11	178.0 (2)	C12—C13—C18—C17	176.4 (2)
O1—C1—C2—C3	−178.2 (3)	C14—C13—C18—O2	−178.6 (2)
O1—C1—C6—C5	178.4 (2)	C14—C13—C18—C17	0.1 (3)
O1—C1—C6—C7	2.4 (4)	C18—C13—C14—C15	1.1 (4)
C2—C1—C6—C5	−1.2 (4)	C13—C14—C15—Cl2	176.9 (2)
C2—C1—C6—C7	−177.2 (2)	C13—C14—C15—C16	−1.6 (4)
C6—C1—C2—C3	1.4 (5)	Cl2—C15—C16—C17	−177.5 (2)
C1—C2—C3—C4	−0.3 (5)	C14—C15—C16—C17	1.0 (5)
C2—C3—C4—Cl1	178.6 (2)	C15—C16—C17—C18	0.2 (5)
C2—C3—C4—C5	−1.2 (5)	C16—C17—C18—O2	178.0 (3)
Cl1—C4—C5—C6	−178.4 (2)	C16—C17—C18—C13	−0.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.85	1.88	2.649 (3)	150
O2—H20···N2	0.85	1.87	2.647 (3)	151
C7—H6···O2ⁱ	0.95	2.59	3.230 (3)	125
C12—H15···O1ⁱⁱ	0.95	2.57	3.300 (3)	134

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+3/2, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀Cl₂N₂O₂
M_r	367.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	14.055 (4), 21.214 (11), 11.873 (3)
V (Å³)	3540 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.18 × 0.13 × 0.13

Data collection
Diffractometer	Rigaku AFC-7R diffractometer
Absorption correction	–
No. of measured, independent and observed [F² > 2σ(F²)] reflections	5928, 4066, 2735
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.105, 1.00
No. of reflections	2739
No. of parameters	237
No. of restraints	?
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.45

Computer programs: WinAFC (Rigaku/MSC, 2006), CrystalStructure (Rigaku/MSC, 2006), SIR92 (Altomare et al., 1993), CRYSTALS (Betteridge et al., 2003), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.848	1.881	2.649 (3)	149.9
O2—H20···N2	0.852	1.868	2.647 (3)	151.2
C7—H6···O2ⁱ	0.950	2.589	3.230 (3)	125.1
C12—H15···O1ⁱⁱ	0.950	2.565	3.300 (3)	134.3

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+3/2, −y, z+1/2.

Acknowledgements

This study was supported financially in part by Grants-in-Aid (Nos. 19550040 and 20550075) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

References

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