4,4'-[Piperazine-1,4-diylbis(propyl-ene-nitrilo-methyl-idyne)]diphenol.

In the title mol-ecule, C(24)H(32)N(4)O(2), the piperazine ring adopts a chair conformation and the dihedral angle between the two benzene rings is 35.4 (1)°. In the crystal structure, inter-molecular O-H⋯N hydrogen bonds link mol-ecules into chains along [001].

Related literature

For the properties of piperazine derivatives, see: Keypour et al. (2008 ▶, 2009 ▶); Paital et al. (2009 ▶). For related structures, see: Thirumurugan et al. (1998 ▶); Yogavel et al. (2003 ▶).

Experimental

Crystal data

C24H32N4O2

M = 408.54

Monoclinic,

a = 5.9701 (10) Å

b = 30.159 (3) Å

c = 12.8348 (18) Å

β = 97.558 (2)°

V = 2290.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.17 × 0.15 × 0.11 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.987, T max = 0.992

5997 measured reflections

2016 independent reflections

1387 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.103

S = 0.96

2016 reflections

271 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045620/lh2937sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045620/lh2937Isup2.hkl

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

C24H32N4O2	F(000) = 880
Mr = 408.54	Dx = 1.185 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1760 reflections
a = 5.9701 (10) Å	θ = 2.7–24.9°
b = 30.159 (3) Å	µ = 0.08 mm−1
c = 12.8348 (18) Å	T = 298 K
β = 97.558 (2)°	Lamellate, pink
V = 2290.9 (6) Å3	0.17 × 0.15 × 0.11 mm
Z = 4

Siemens SMART CCD diffractometer	2016 independent reflections
Radiation source: fine-focus sealed tube	1387 reflections with I > 2σ(I)
graphite	Rint = 0.068
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→6
Tmin = 0.987, Tmax = 0.992	k = −30→35
5997 measured reflections	l = −15→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0507P)2] where P = (Fo2 + 2Fc2)/3
2016 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.19 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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.

	x	y	z	Uiso*/Ueq
N1	0.6528 (5)	0.39796 (9)	0.5395 (2)	0.0440 (7)
N2	0.6327 (5)	0.34403 (9)	0.7270 (2)	0.0450 (7)
N3	0.6917 (7)	0.47133 (10)	0.2563 (2)	0.0619 (9)
N4	0.5753 (7)	0.26995 (10)	1.0120 (2)	0.0604 (9)
O1	1.0094 (5)	0.38009 (9)	−0.1521 (2)	0.0684 (8)
H1	0.8981	0.3653	−0.1744	0.103*
O2	0.2701 (4)	0.37289 (8)	1.40788 (19)	0.0592 (7)
H2	0.3880	0.3735	1.4486	0.089*
C1	0.5611 (7)	0.41527 (12)	0.6330 (3)	0.0509 (10)
H1A	0.4439	0.4369	0.6113	0.061*
H1B	0.6804	0.4300	0.6789	0.061*
C2	0.4643 (7)	0.37801 (12)	0.6919 (3)	0.0524 (10)
H2A	0.4043	0.3901	0.7526	0.063*
H2B	0.3403	0.3644	0.6467	0.063*
C3	0.7284 (7)	0.32708 (12)	0.6338 (3)	0.0510 (10)
H3A	0.6111	0.3122	0.5871	0.061*
H3B	0.8464	0.3057	0.6560	0.061*
C4	0.8247 (6)	0.36472 (12)	0.5762 (3)	0.0504 (10)
H4A	0.9453	0.3788	0.6226	0.060*
H4B	0.8890	0.3530	0.5163	0.060*
C5	0.7518 (7)	0.43362 (13)	0.4807 (3)	0.0552 (10)
H5A	0.8202	0.4203	0.4237	0.066*
H5B	0.8712	0.4479	0.5273	0.066*
C6	0.5862 (8)	0.46839 (13)	0.4356 (3)	0.0628 (11)
H6A	0.5490	0.4873	0.4920	0.075*
H6B	0.4481	0.4540	0.4044	0.075*
C7	0.6779 (9)	0.49699 (13)	0.3524 (3)	0.0680 (12)
H7A	0.5796	0.5224	0.3361	0.082*
H7B	0.8268	0.5079	0.3798	0.082*
C8	0.8797 (8)	0.46994 (12)	0.2204 (3)	0.0555 (11)
H8	1.0022	0.4850	0.2563	0.067*
C9	0.9117 (7)	0.44553 (11)	0.1246 (3)	0.0479 (9)
C10	1.1116 (7)	0.44905 (13)	0.0817 (3)	0.0608 (10)
H10	1.2280	0.4664	0.1153	0.073*
C11	1.1427 (7)	0.42709 (14)	−0.0112 (3)	0.0584 (10)
H11	1.2774	0.4304	−0.0395	0.070*
C12	0.9734 (6)	0.40044 (12)	−0.0611 (3)	0.0471 (9)
C13	0.7736 (6)	0.39566 (12)	−0.0171 (3)	0.0501 (10)
H13	0.6592	0.3775	−0.0497	0.060*
C14	0.7435 (6)	0.41775 (12)	0.0751 (3)	0.0472 (9)
H14	0.6100	0.4140	0.1041	0.057*
C15	0.5266 (7)	0.30844 (12)	0.7830 (3)	0.0566 (10)
H15A	0.4159	0.2933	0.7332	0.068*
H15B	0.4465	0.3219	0.8360	0.068*
C16	0.6907 (8)	0.27448 (12)	0.8355 (3)	0.0591 (11)
H16A	0.8220	0.2896	0.8713	0.071*
H16B	0.7411	0.2555	0.7821	0.071*
C17	0.5864 (9)	0.24597 (14)	0.9141 (3)	0.0703 (13)
H17A	0.4353	0.2372	0.8841	0.084*
H17B	0.6759	0.2193	0.9286	0.084*
C18	0.3869 (7)	0.28242 (12)	1.0347 (3)	0.0530 (10)
H18	0.2584	0.2760	0.9879	0.064*
C19	0.3598 (7)	0.30661 (11)	1.1315 (3)	0.0446 (9)
C20	0.5407 (7)	0.31283 (13)	1.2093 (3)	0.0563 (11)
H20	0.6820	0.3019	1.1994	0.068*
C21	0.5156 (7)	0.33506 (13)	1.3016 (3)	0.0566 (10)
H21	0.6392	0.3387	1.3530	0.068*
C22	0.3063 (6)	0.35184 (11)	1.3173 (3)	0.0462 (9)
C23	0.1256 (7)	0.34603 (12)	1.2404 (3)	0.0517 (9)
H23	−0.0150	0.3574	1.2501	0.062*
C24	0.1506 (7)	0.32352 (12)	1.1488 (3)	0.0545 (10)
H24	0.0260	0.3196	1.0980	0.065*

	U11	U22	U33	U12	U13	U23
N1	0.0460 (18)	0.0507 (17)	0.0371 (16)	0.0038 (15)	0.0126 (15)	−0.0067 (14)
N2	0.0486 (18)	0.0493 (17)	0.0378 (16)	0.0054 (15)	0.0086 (14)	−0.0041 (14)
N3	0.086 (3)	0.053 (2)	0.047 (2)	−0.0058 (19)	0.0136 (19)	−0.0030 (17)
N4	0.084 (3)	0.0542 (19)	0.045 (2)	0.0001 (19)	0.0140 (19)	−0.0078 (16)
O1	0.0580 (18)	0.092 (2)	0.0577 (17)	−0.0007 (15)	0.0161 (15)	−0.0221 (16)
O2	0.0517 (17)	0.0707 (18)	0.0567 (17)	0.0012 (14)	0.0131 (14)	−0.0143 (14)
C1	0.060 (2)	0.054 (2)	0.041 (2)	0.0106 (19)	0.0137 (19)	−0.0060 (18)
C2	0.049 (2)	0.067 (2)	0.043 (2)	0.012 (2)	0.0145 (19)	−0.0047 (19)
C3	0.057 (2)	0.054 (2)	0.043 (2)	0.0123 (19)	0.0086 (19)	−0.0054 (18)
C4	0.045 (2)	0.065 (3)	0.042 (2)	0.0102 (18)	0.0110 (18)	−0.0056 (19)
C5	0.063 (3)	0.058 (2)	0.046 (2)	−0.007 (2)	0.014 (2)	−0.0035 (19)
C6	0.083 (3)	0.052 (2)	0.056 (3)	0.003 (2)	0.019 (2)	−0.002 (2)
C7	0.105 (4)	0.049 (2)	0.052 (2)	−0.004 (2)	0.019 (2)	−0.008 (2)
C8	0.070 (3)	0.049 (2)	0.047 (2)	−0.005 (2)	0.004 (2)	−0.0016 (18)
C9	0.055 (2)	0.043 (2)	0.044 (2)	0.0047 (18)	0.0010 (19)	0.0022 (17)
C10	0.054 (3)	0.069 (3)	0.057 (2)	−0.009 (2)	−0.001 (2)	−0.007 (2)
C11	0.046 (2)	0.073 (3)	0.056 (2)	0.001 (2)	0.008 (2)	−0.003 (2)
C12	0.047 (2)	0.051 (2)	0.042 (2)	0.0076 (18)	0.0023 (19)	0.0014 (19)
C13	0.052 (2)	0.049 (2)	0.049 (2)	−0.0023 (18)	0.003 (2)	−0.0043 (18)
C14	0.049 (2)	0.049 (2)	0.045 (2)	0.0014 (18)	0.0081 (18)	0.0016 (18)
C15	0.059 (2)	0.064 (2)	0.048 (2)	−0.008 (2)	0.0096 (19)	−0.005 (2)
C16	0.083 (3)	0.050 (2)	0.045 (2)	0.012 (2)	0.012 (2)	−0.0052 (19)
C17	0.113 (4)	0.052 (2)	0.048 (2)	0.001 (3)	0.018 (3)	−0.005 (2)
C18	0.066 (3)	0.049 (2)	0.042 (2)	−0.011 (2)	0.001 (2)	0.0043 (18)
C19	0.055 (2)	0.045 (2)	0.0339 (19)	−0.0059 (18)	0.0061 (17)	0.0028 (16)
C20	0.052 (2)	0.068 (3)	0.051 (2)	0.000 (2)	0.014 (2)	−0.010 (2)
C21	0.047 (2)	0.077 (3)	0.046 (2)	−0.006 (2)	0.005 (2)	−0.016 (2)
C22	0.050 (2)	0.046 (2)	0.044 (2)	−0.0031 (19)	0.010 (2)	−0.0013 (18)
C23	0.047 (2)	0.055 (2)	0.053 (2)	0.0088 (19)	0.006 (2)	0.0049 (19)
C24	0.054 (2)	0.058 (2)	0.047 (2)	0.001 (2)	−0.0086 (19)	0.0080 (19)

N1—C4	1.467 (5)	C8—C9	1.466 (5)
N1—C1	1.478 (4)	C8—H8	0.9300
N1—C5	1.481 (4)	C9—C10	1.383 (5)
N2—C2	1.465 (5)	C9—C14	1.395 (5)
N2—C15	1.479 (4)	C10—C11	1.398 (5)
N2—C3	1.483 (4)	C10—H10	0.9300
N3—C8	1.269 (5)	C11—C12	1.381 (6)
N3—C7	1.467 (5)	C11—H11	0.9300
N4—C18	1.256 (5)	C12—C13	1.392 (5)
N4—C17	1.458 (5)	C13—C14	1.390 (5)
O1—C12	1.361 (4)	C13—H13	0.9300
O1—H1	0.8200	C14—H14	0.9300
O2—C22	1.367 (4)	C15—C16	1.513 (6)
O2—H2	0.8200	C15—H15A	0.9700
C1—C2	1.511 (5)	C15—H15B	0.9700
C1—H1A	0.9700	C16—C17	1.520 (5)
C1—H1B	0.9700	C16—H16A	0.9700
C2—H2A	0.9700	C16—H16B	0.9700
C2—H2B	0.9700	C17—H17A	0.9700
C3—C4	1.509 (5)	C17—H17B	0.9700
C3—H3A	0.9700	C18—C19	1.468 (5)
C3—H3B	0.9700	C18—H18	0.9300
C4—H4A	0.9700	C19—C20	1.384 (5)
C4—H4B	0.9700	C19—C24	1.394 (5)
C5—C6	1.504 (6)	C20—C21	1.386 (5)
C5—H5A	0.9700	C20—H20	0.9300
C5—H5B	0.9700	C21—C22	1.387 (5)
C6—C7	1.529 (6)	C21—H21	0.9300
C6—H6A	0.9700	C22—C23	1.374 (5)
C6—H6B	0.9700	C23—C24	1.382 (5)
C7—H7A	0.9700	C23—H23	0.9300
C7—H7B	0.9700	C24—H24	0.9300
C4—N1—C1	107.4 (3)	C10—C9—C8	120.7 (4)
C4—N1—C5	110.5 (3)	C14—C9—C8	121.2 (4)
C1—N1—C5	111.9 (3)	C9—C10—C11	121.5 (4)
C2—N2—C15	109.7 (3)	C9—C10—H10	119.3
C2—N2—C3	108.3 (3)	C11—C10—H10	119.3
C15—N2—C3	112.1 (3)	C12—C11—C10	120.0 (4)
C8—N3—C7	118.2 (4)	C12—C11—H11	120.0
C18—N4—C17	119.5 (4)	C10—C11—H11	120.0
C12—O1—H1	109.5	O1—C12—C11	118.1 (3)
C22—O2—H2	109.5	O1—C12—C13	122.8 (3)
N1—C1—C2	110.5 (3)	C11—C12—C13	119.1 (3)
N1—C1—H1A	109.5	C14—C13—C12	120.6 (3)
C2—C1—H1A	109.5	C14—C13—H13	119.7
N1—C1—H1B	109.5	C12—C13—H13	119.7
C2—C1—H1B	109.5	C13—C14—C9	120.7 (3)
H1A—C1—H1B	108.1	C13—C14—H14	119.7
N2—C2—C1	112.5 (3)	C9—C14—H14	119.7
N2—C2—H2A	109.1	N2—C15—C16	114.4 (3)
C1—C2—H2A	109.1	N2—C15—H15A	108.7
N2—C2—H2B	109.1	C16—C15—H15A	108.7
C1—C2—H2B	109.1	N2—C15—H15B	108.7
H2A—C2—H2B	107.8	C16—C15—H15B	108.7
N2—C3—C4	110.4 (3)	H15A—C15—H15B	107.6
N2—C3—H3A	109.6	C15—C16—C17	112.4 (4)
C4—C3—H3A	109.6	C15—C16—H16A	109.1
N2—C3—H3B	109.6	C17—C16—H16A	109.1
C4—C3—H3B	109.6	C15—C16—H16B	109.1
H3A—C3—H3B	108.1	C17—C16—H16B	109.1
N1—C4—C3	112.1 (3)	H16A—C16—H16B	107.9
N1—C4—H4A	109.2	N4—C17—C16	111.1 (3)
C3—C4—H4A	109.2	N4—C17—H17A	109.4
N1—C4—H4B	109.2	C16—C17—H17A	109.4
C3—C4—H4B	109.2	N4—C17—H17B	109.4
H4A—C4—H4B	107.9	C16—C17—H17B	109.4
N1—C5—C6	114.6 (3)	H17A—C17—H17B	108.0
N1—C5—H5A	108.6	N4—C18—C19	123.2 (4)
C6—C5—H5A	108.6	N4—C18—H18	118.4
N1—C5—H5B	108.6	C19—C18—H18	118.4
C6—C5—H5B	108.6	C20—C19—C24	117.8 (3)
H5A—C5—H5B	107.6	C20—C19—C18	121.0 (4)
C5—C6—C7	112.6 (4)	C24—C19—C18	121.2 (4)
C5—C6—H6A	109.1	C19—C20—C21	121.3 (4)
C7—C6—H6A	109.1	C19—C20—H20	119.3
C5—C6—H6B	109.1	C21—C20—H20	119.3
C7—C6—H6B	109.1	C20—C21—C22	120.1 (4)
H6A—C6—H6B	107.8	C20—C21—H21	120.0
N3—C7—C6	110.8 (3)	C22—C21—H21	120.0
N3—C7—H7A	109.5	O2—C22—C23	118.2 (3)
C6—C7—H7A	109.5	O2—C22—C21	122.6 (3)
N3—C7—H7B	109.5	C23—C22—C21	119.1 (3)
C6—C7—H7B	109.5	C22—C23—C24	120.7 (3)
H7A—C7—H7B	108.1	C22—C23—H23	119.6
N3—C8—C9	122.7 (4)	C24—C23—H23	119.6
N3—C8—H8	118.6	C23—C24—C19	120.9 (4)
C9—C8—H8	118.6	C23—C24—H24	119.5
C10—C9—C14	118.1 (3)	C19—C24—H24	119.5
C4—N1—C1—C2	−57.8 (4)	O1—C12—C13—C14	−178.9 (3)
C5—N1—C1—C2	−179.3 (3)	C11—C12—C13—C14	0.7 (6)
C15—N2—C2—C1	−179.4 (3)	C12—C13—C14—C9	0.8 (5)
C3—N2—C2—C1	−56.8 (4)	C10—C9—C14—C13	−2.5 (5)
N1—C1—C2—N2	59.2 (4)	C8—C9—C14—C13	178.4 (3)
C2—N2—C3—C4	56.1 (4)	C2—N2—C15—C16	−172.3 (3)
C15—N2—C3—C4	177.3 (3)	C3—N2—C15—C16	67.3 (4)
C1—N1—C4—C3	59.4 (4)	N2—C15—C16—C17	165.2 (3)
C5—N1—C4—C3	−178.3 (3)	C18—N4—C17—C16	109.1 (5)
N2—C3—C4—N1	−60.0 (4)	C15—C16—C17—N4	−77.3 (5)
C4—N1—C5—C6	177.5 (3)	C17—N4—C18—C19	179.8 (3)
C1—N1—C5—C6	−62.9 (4)	N4—C18—C19—C20	−7.1 (5)
N1—C5—C6—C7	−164.6 (3)	N4—C18—C19—C24	173.7 (3)
C8—N3—C7—C6	−125.9 (4)	C24—C19—C20—C21	0.1 (5)
C5—C6—C7—N3	70.6 (5)	C18—C19—C20—C21	−179.0 (3)
C7—N3—C8—C9	−179.6 (3)	C19—C20—C21—C22	−0.4 (6)
N3—C8—C9—C10	172.5 (4)	C20—C21—C22—O2	178.0 (3)
N3—C8—C9—C14	−8.3 (5)	C20—C21—C22—C23	0.1 (5)
C14—C9—C10—C11	2.7 (6)	O2—C22—C23—C24	−177.6 (3)
C8—C9—C10—C11	−178.1 (3)	C21—C22—C23—C24	0.4 (5)
C9—C10—C11—C12	−1.3 (6)	C22—C23—C24—C19	−0.7 (5)
C10—C11—C12—O1	179.2 (3)	C20—C19—C24—C23	0.4 (5)
C10—C11—C12—C13	−0.4 (6)	C18—C19—C24—C23	179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1i	0.82	1.98	2.762 (4)	159
O1—H1···N2ii	0.82	2.00	2.780 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1i	0.82	1.98	2.762 (4)	159
O1—H1⋯N2ii	0.82	2.00	2.780 (4)	159

Symmetry codes: (i) ; (ii) .