4,4'-Dichloro-2,2'-(piperazine-1,4-diyldimethyl-ene)diphenol.

In the titile compound, C(18)H(20)Cl(2)N(2)O(2), the piperazine ring adopts a chair conformation. The mol-ecule has a non-crystallographic inversion centre in the middle of the piperazine ring at approximate position (3/4, 1/8, 3/8). There are intra-molecular O-H⋯N hydrogen bonds forming S(6) ring motifs. Inter-molecular C-H⋯O hydrogen bonds generate anti-parallel 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)R(6) (6)(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 = 367.26

Orthorhombic,

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 F 2 > 2σ(F 2)

R int = 0.039

3 standard reflections every 150 reflections intensity decay: 0.7%

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.00

2739 reflections

237 parameters

All H-atom parameters refined

Δρmax = 0.33 e Å−3

Δρmin = −0.45 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H20Cl2N2O2	F000 = 1536.00
Mr = 367.26	Dx = 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 = 13.7–16.9º
b = 21.214 (11) Å	µ = 0.38 mm−1
c = 11.873 (3) Å	T = 298.1 K
V = 3540 (2) Å3	Prismatic, colorless
Z = 8	0.18 × 0.13 × 0.13 mm

Rigaku AFC-7R diffractometer	θmax = 27.5º
ω scans	h = −10→18
Absorption correction: none	k = 0→27
5928 measured reflections	l = −8→15
4066 independent reflections	3 standard reflections
2735 reflections with F2 > 2σ(F2)	every 150 reflections
Rint = 0.039	intensity decay: 0.7%

Refinement on F2	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.039	w = 1/[0.0011Fo2 + σ(Fo2)]/(4Fo2)
wR(F2) = 0.105	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.33 e Å−3
2739 reflections	Δρmin = −0.45 e Å−3
237 parameters	Extinction correction: none

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).

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .