(1Z,1'Z,3E,3'E)-1,1'-Diphenyl-3,3'-[(1S,2S)-cyclo-hexane-1,2-diyldinitrilo]dibut-1-en-1-ol.

A new tetra-dentate chiral Schiff base ligand, C(26)H(30)N(2)O(2), has been synthesized by the reaction of 1-phenyl-butane-1,3-dione with (1S,2S)-(-)-1,2-diamino-cyclo-hexane. The chiral centers in the mol-ecule have the same S configuration, since the absolute configuration was determined by that of the starting reagent (1S,2S)-(-)-1,2-diamino-hexane. The cyclo-hexane ring is in a chair conformation, and the substituents are equatorial in the most stable conformation (trans-cyclo-hexyl). The crystal structure is stabilized by two intra-molecular O-H⋯N hydrogen bonds and a weak C-H⋯π inter-action.

Related literature

For the chemistry of Schiff bases, see: Alemi & Shaabani (2000 ▶); Bandini et al. (1999 ▶, 2000 ▶); Belokon et al. (1997 ▶); Cozzi (2003 ▶); Jiang et al. (1995 ▶); Kureshy et al. (2001 ▶); Sasaki et al. (1991 ▶).

Experimental

Crystal data

C26H30N2O2

M = 402.52

Orthorhombic,

a = 8.9073 (11) Å

b = 10.1205 (13) Å

c = 26.476 (3) Å

V = 2386.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 (2) K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.980, T max = 0.990

22130 measured reflections

2683 independent reflections

1952 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.159

S = 1.07

2683 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014670/bx2143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014670/bx2143Isup2.hkl

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

C26H30N2O2	F000 = 864
Mr = 402.52	Dx = 1.120 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4136 reflections
a = 8.9073 (11) Å	θ = 3.1–27.5º
b = 10.1205 (13) Å	µ = 0.07 mm−1
c = 26.476 (3) Å	T = 293 (2) K
V = 2386.7 (5) Å3	Block, colorless
Z = 4	0.20 × 0.20 × 0.20 mm

Rigaku SCXmini diffractometer	2683 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.062
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0º
T = 293(2) K	θmin = 2.4º
ω scans	h = −10→10
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −12→12
Tmin = 0.980, Tmax = 0.990	l = −32→32
22130 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.0753P)2 + 0.2595P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2683 reflections	Δρmax = 0.29 e Å−3
275 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N2	0.8242 (3)	0.2435 (3)	0.96116 (10)	0.0576 (7)
C17	0.8209 (4)	0.1345 (3)	0.92486 (12)	0.0562 (8)
H17	0.9072	0.1434	0.9021	0.067*
N1	0.6697 (4)	0.2620 (3)	0.86429 (10)	0.0618 (8)
O2	0.7103 (3)	0.3353 (2)	1.04671 (9)	0.0684 (7)
H2A	0.7189	0.2838	1.0230	0.103*
C1'	0.7786 (4)	0.4406 (3)	1.03675 (13)	0.0582 (8)
C18	0.8342 (5)	0.0039 (3)	0.95283 (14)	0.0669 (10)
H18A	0.9290	0.0014	0.9708	0.080*
H18B	0.7541	−0.0025	0.9776	0.080*
C2	0.6168 (4)	0.4861 (4)	0.84749 (13)	0.0597 (9)
H2	0.5630	0.5613	0.8564	0.072*
C3'	0.8907 (4)	0.3615 (4)	0.95676 (13)	0.0571 (8)
C3	0.5973 (4)	0.3737 (4)	0.87611 (13)	0.0597 (9)
C21	0.6703 (6)	0.0219 (4)	0.85724 (15)	0.0776 (12)
H21A	0.5761	0.0238	0.8389	0.093*
H21B	0.7512	0.0291	0.8329	0.093*
O1	0.7936 (4)	0.3983 (3)	0.79076 (10)	0.0852 (9)
H1	0.7875	0.3376	0.8112	0.128*
C16	0.6767 (4)	0.1386 (3)	0.89317 (13)	0.0584 (9)
H16	0.5899	0.1345	0.9159	0.070*
C4	0.7242 (4)	0.6191 (4)	0.77629 (13)	0.0653 (10)
C2'	0.8698 (4)	0.4569 (4)	0.99355 (13)	0.0618 (9)
H2'	0.9192	0.5372	0.9896	0.074*
C10	0.7610 (4)	0.5522 (4)	1.07347 (14)	0.0648 (9)
C23	0.9890 (5)	0.3907 (4)	0.91182 (14)	0.0684 (10)
H23A	0.9330	0.3765	0.8813	0.103*
H23B	1.0747	0.3332	0.9123	0.103*
H23C	1.0219	0.4809	0.9132	0.103*
C1	0.7137 (4)	0.4938 (4)	0.80549 (13)	0.0629 (9)
C22	0.4918 (5)	0.3766 (4)	0.92075 (15)	0.0778 (12)
H22A	0.5438	0.3469	0.9504	0.117*
H22B	0.4079	0.3194	0.9143	0.117*
H22C	0.4565	0.4652	0.9259	0.117*
C19	0.8253 (5)	−0.1133 (4)	0.91717 (15)	0.0772 (11)
H19A	0.9126	−0.1136	0.8953	0.093*
H19B	0.8262	−0.1946	0.9366	0.093*
C20	0.6840 (6)	−0.1081 (4)	0.88527 (18)	0.0847 (12)
H20A	0.6855	−0.1801	0.8611	0.102*
H20B	0.5971	−0.1197	0.9069	0.102*
C15	0.7371 (5)	0.5242 (4)	1.12405 (15)	0.0771 (11)
H15	0.7328	0.4368	1.1348	0.093*
C9	0.6005 (5)	0.6985 (4)	0.76822 (16)	0.0787 (12)
H9	0.5080	0.6744	0.7817	0.094*
C11	0.7644 (5)	0.6836 (4)	1.05852 (18)	0.0824 (13)
H11	0.7793	0.7047	1.0247	0.099*
C12	0.7458 (6)	0.7824 (5)	1.0933 (2)	0.1040 (17)
H12	0.7483	0.8701	1.0828	0.125*
C8	0.6128 (7)	0.8127 (5)	0.74050 (19)	0.1055 (17)
H8	0.5290	0.8658	0.7352	0.127*
C14	0.7197 (7)	0.6255 (5)	1.15854 (18)	0.1006 (16)
H14	0.7049	0.6065	1.1925	0.121*
C5	0.8588 (5)	0.6560 (6)	0.75543 (18)	0.1002 (16)
H5	0.9425	0.6022	0.7597	0.120*
C13	0.7242 (6)	0.7548 (6)	1.1424 (2)	0.1062 (18)
H13	0.7123	0.8232	1.1655	0.127*
C6	0.8718 (8)	0.7720 (7)	0.7282 (3)	0.133 (2)
H6	0.9640	0.7979	0.7150	0.160*
C7	0.7471 (11)	0.8477 (6)	0.7210 (2)	0.126 (2)
H7	0.7546	0.9251	0.7023	0.152*

	U11	U22	U33	U12	U13	U23
N2	0.0638 (17)	0.0557 (16)	0.0532 (15)	−0.0045 (15)	0.0003 (14)	−0.0004 (14)
C17	0.061 (2)	0.0553 (19)	0.0528 (17)	0.0016 (18)	0.0041 (16)	0.0009 (16)
N1	0.0690 (19)	0.0633 (18)	0.0531 (15)	0.0081 (17)	−0.0017 (15)	0.0041 (14)
O2	0.0813 (18)	0.0624 (15)	0.0614 (14)	−0.0075 (15)	0.0111 (14)	−0.0046 (12)
C1'	0.062 (2)	0.0504 (18)	0.0618 (19)	−0.0020 (18)	−0.0071 (18)	0.0042 (17)
C18	0.077 (3)	0.059 (2)	0.065 (2)	0.003 (2)	−0.006 (2)	0.0059 (18)
C2	0.063 (2)	0.061 (2)	0.0551 (18)	0.0043 (18)	0.0048 (17)	0.0030 (17)
C3'	0.0552 (19)	0.0579 (19)	0.0582 (19)	−0.0051 (17)	−0.0012 (17)	0.0089 (17)
C3	0.059 (2)	0.070 (2)	0.0505 (18)	0.006 (2)	0.0025 (16)	0.0044 (18)
C21	0.091 (3)	0.073 (3)	0.069 (2)	−0.002 (2)	−0.013 (2)	−0.011 (2)
O1	0.091 (2)	0.097 (2)	0.0675 (16)	0.0300 (19)	0.0233 (16)	0.0236 (15)
C16	0.065 (2)	0.0539 (19)	0.0566 (18)	0.0023 (19)	0.0052 (18)	0.0011 (16)
C4	0.065 (2)	0.077 (2)	0.0537 (18)	−0.010 (2)	−0.0035 (18)	0.0070 (19)
C2'	0.067 (2)	0.0527 (19)	0.066 (2)	−0.0099 (18)	0.0021 (18)	0.0005 (18)
C10	0.061 (2)	0.061 (2)	0.072 (2)	0.0020 (19)	−0.0050 (19)	−0.0072 (19)
C23	0.067 (2)	0.072 (2)	0.066 (2)	−0.007 (2)	0.0063 (19)	0.008 (2)
C1	0.058 (2)	0.074 (2)	0.0565 (18)	0.009 (2)	0.0001 (17)	0.0050 (19)
C22	0.080 (3)	0.083 (3)	0.070 (2)	0.014 (2)	0.026 (2)	0.014 (2)
C19	0.090 (3)	0.056 (2)	0.086 (3)	0.006 (2)	0.004 (2)	0.001 (2)
C20	0.100 (3)	0.060 (2)	0.094 (3)	−0.001 (2)	−0.003 (3)	−0.015 (2)
C15	0.082 (3)	0.083 (3)	0.067 (2)	0.004 (2)	−0.005 (2)	−0.008 (2)
C9	0.078 (3)	0.083 (3)	0.076 (3)	0.001 (2)	−0.012 (2)	0.020 (2)
C11	0.088 (3)	0.064 (2)	0.095 (3)	0.000 (2)	0.007 (3)	−0.001 (2)
C12	0.106 (4)	0.064 (3)	0.142 (5)	0.002 (3)	0.016 (4)	−0.023 (3)
C8	0.136 (5)	0.090 (3)	0.090 (3)	−0.001 (4)	−0.018 (3)	0.031 (3)
C14	0.110 (4)	0.114 (4)	0.078 (3)	0.014 (4)	−0.010 (3)	−0.030 (3)
C5	0.077 (3)	0.124 (4)	0.100 (3)	−0.017 (3)	0.012 (3)	0.031 (3)
C13	0.096 (4)	0.091 (4)	0.131 (5)	0.001 (3)	0.001 (4)	−0.054 (4)
C6	0.120 (5)	0.149 (6)	0.130 (5)	−0.056 (5)	0.021 (4)	0.039 (5)
C7	0.180 (7)	0.099 (4)	0.100 (4)	−0.037 (5)	−0.006 (5)	0.034 (3)

N2—C3'	1.338 (4)	C10—C15	1.385 (5)
N2—C17	1.463 (4)	C10—C11	1.388 (5)
C17—C18	1.520 (5)	C23—H23A	0.9600
C17—C16	1.535 (5)	C23—H23B	0.9600
C17—H17	0.9800	C23—H23C	0.9600
N1—C3	1.339 (5)	C22—H22A	0.9600
N1—C16	1.465 (4)	C22—H22B	0.9600
O2—C1'	1.255 (4)	C22—H22C	0.9600
O2—H2A	0.8200	C19—C20	1.517 (6)
C1'—C2'	1.413 (5)	C19—H19A	0.9700
C1'—C10	1.498 (5)	C19—H19B	0.9700
C18—C19	1.518 (5)	C20—H20A	0.9700
C18—H18A	0.9700	C20—H20B	0.9700
C18—H18B	0.9700	C15—C14	1.382 (6)
C2—C3	1.378 (5)	C15—H15	0.9300
C2—C1	1.409 (5)	C9—C8	1.374 (6)
C2—H2	0.9300	C9—H9	0.9300
C3'—C2'	1.384 (5)	C11—C12	1.370 (6)
C3'—C23	1.506 (5)	C11—H11	0.9300
C3—C22	1.510 (5)	C12—C13	1.341 (7)
C21—C20	1.515 (5)	C12—H12	0.9300
C21—C16	1.517 (5)	C8—C7	1.350 (8)
C21—H21A	0.9700	C8—H8	0.9300
C21—H21B	0.9700	C14—C13	1.377 (7)
O1—C1	1.262 (4)	C14—H14	0.9300
O1—H1	0.8200	C5—C6	1.382 (8)
C16—H16	0.9800	C5—H5	0.9300
C4—C5	1.372 (6)	C13—H13	0.9300
C4—C9	1.380 (5)	C6—C7	1.363 (9)
C4—C1	1.488 (5)	C6—H6	0.9300
C2'—H2'	0.9300	C7—H7	0.9300
C3'—N2—C17	128.6 (3)	H23A—C23—H23C	109.5
N2—C17—C18	109.5 (3)	H23B—C23—H23C	109.5
N2—C17—C16	110.8 (3)	O1—C1—C2	123.2 (3)
C18—C17—C16	110.8 (3)	O1—C1—C4	117.2 (3)
N2—C17—H17	108.6	C2—C1—C4	119.7 (3)
C18—C17—H17	108.6	C3—C22—H22A	109.5
C16—C17—H17	108.6	C3—C22—H22B	109.5
C3—N1—C16	128.2 (3)	H22A—C22—H22B	109.5
C1'—O2—H2A	109.5	C3—C22—H22C	109.5
O2—C1'—C2'	123.2 (3)	H22A—C22—H22C	109.5
O2—C1'—C10	116.9 (3)	H22B—C22—H22C	109.5
C2'—C1'—C10	119.8 (3)	C20—C19—C18	111.2 (3)
C19—C18—C17	111.9 (3)	C20—C19—H19A	109.4
C19—C18—H18A	109.2	C18—C19—H19A	109.4
C17—C18—H18A	109.2	C20—C19—H19B	109.4
C19—C18—H18B	109.2	C18—C19—H19B	109.4
C17—C18—H18B	109.2	H19A—C19—H19B	108.0
H18A—C18—H18B	107.9	C21—C20—C19	111.7 (4)
C3—C2—C1	123.8 (3)	C21—C20—H20A	109.3
C3—C2—H2	118.1	C19—C20—H20A	109.3
C1—C2—H2	118.1	C21—C20—H20B	109.3
N2—C3'—C2'	120.1 (3)	C19—C20—H20B	109.3
N2—C3'—C23	120.1 (3)	H20A—C20—H20B	107.9
C2'—C3'—C23	119.8 (3)	C14—C15—C10	120.3 (4)
N1—C3—C2	120.5 (3)	C14—C15—H15	119.9
N1—C3—C22	119.9 (3)	C10—C15—H15	119.9
C2—C3—C22	119.6 (3)	C8—C9—C4	120.6 (5)
C20—C21—C16	111.5 (3)	C8—C9—H9	119.7
C20—C21—H21A	109.3	C4—C9—H9	119.7
C16—C21—H21A	109.3	C12—C11—C10	120.3 (5)
C20—C21—H21B	109.3	C12—C11—H11	119.8
C16—C21—H21B	109.3	C10—C11—H11	119.8
H21A—C21—H21B	108.0	C13—C12—C11	121.1 (5)
C1—O1—H1	109.5	C13—C12—H12	119.4
N1—C16—C21	109.5 (3)	C11—C12—H12	119.4
N1—C16—C17	110.1 (3)	C7—C8—C9	119.7 (6)
C21—C16—C17	110.7 (3)	C7—C8—H8	120.2
N1—C16—H16	108.8	C9—C8—H8	120.2
C21—C16—H16	108.8	C13—C14—C15	119.8 (5)
C17—C16—H16	108.8	C13—C14—H14	120.1
C5—C4—C9	118.5 (4)	C15—C14—H14	120.1
C5—C4—C1	119.7 (4)	C4—C5—C6	120.9 (6)
C9—C4—C1	121.8 (4)	C4—C5—H5	119.5
C3'—C2'—C1'	124.5 (3)	C6—C5—H5	119.5
C3'—C2'—H2'	117.8	C12—C13—C14	120.2 (5)
C1'—C2'—H2'	117.8	C12—C13—H13	119.9
C15—C10—C11	118.3 (4)	C14—C13—H13	119.9
C15—C10—C1'	119.3 (3)	C7—C6—C5	118.8 (6)
C11—C10—C1'	122.3 (4)	C7—C6—H6	120.6
C3'—C23—H23A	109.5	C5—C6—H6	120.6
C3'—C23—H23B	109.5	C8—C7—C6	121.5 (5)
H23A—C23—H23B	109.5	C8—C7—H7	119.3
C3'—C23—H23C	109.5	C6—C7—H7	119.3
C3'—N2—C17—C18	141.4 (4)	C3—C2—C1—O1	−1.2 (6)
C3'—N2—C17—C16	−96.1 (4)	C3—C2—C1—C4	178.6 (3)
N2—C17—C18—C19	177.8 (3)	C5—C4—C1—O1	−34.7 (6)
C16—C17—C18—C19	55.2 (4)	C9—C4—C1—O1	143.5 (4)
C17—N2—C3'—C2'	174.1 (3)	C5—C4—C1—C2	145.5 (4)
C17—N2—C3'—C23	−6.1 (5)	C9—C4—C1—C2	−36.3 (5)
C16—N1—C3—C2	172.3 (3)	C17—C18—C19—C20	−54.6 (5)
C16—N1—C3—C22	−8.4 (6)	C16—C21—C20—C19	−55.7 (5)
C1—C2—C3—N1	−1.4 (6)	C18—C19—C20—C21	54.4 (5)
C1—C2—C3—C22	179.4 (4)	C11—C10—C15—C14	−1.0 (7)
C3—N1—C16—C21	141.4 (4)	C1'—C10—C15—C14	−179.6 (4)
C3—N1—C16—C17	−96.7 (4)	C5—C4—C9—C8	−0.9 (6)
C20—C21—C16—N1	177.5 (4)	C1—C4—C9—C8	−179.1 (4)
C20—C21—C16—C17	56.0 (5)	C15—C10—C11—C12	0.6 (7)
N2—C17—C16—N1	61.4 (3)	C1'—C10—C11—C12	179.1 (4)
C18—C17—C16—N1	−176.9 (3)	C10—C11—C12—C13	0.0 (9)
N2—C17—C16—C21	−177.4 (3)	C4—C9—C8—C7	0.0 (7)
C18—C17—C16—C21	−55.6 (4)	C10—C15—C14—C13	0.8 (8)
N2—C3'—C2'—C1'	−1.1 (6)	C9—C4—C5—C6	1.9 (7)
C23—C3'—C2'—C1'	179.1 (3)	C1—C4—C5—C6	−179.9 (5)
O2—C1'—C2'—C3'	2.2 (6)	C11—C12—C13—C14	−0.3 (9)
C10—C1'—C2'—C3'	−178.4 (3)	C15—C14—C13—C12	−0.2 (9)
O2—C1'—C10—C15	30.0 (5)	C4—C5—C6—C7	−2.0 (9)
C2'—C1'—C10—C15	−149.4 (4)	C9—C8—C7—C6	0.0 (10)
O2—C1'—C10—C11	−148.5 (4)	C5—C6—C7—C8	1.0 (11)
C2'—C1'—C10—C11	32.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82	1.93	2.650 (3)	146
O1—H1···N1	0.82	1.91	2.629 (4)	145
C19—H19A···Cg3i	0.97	2.96	3.795 (5)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N2	0.82	1.93	2.650 (3)	146
O1—H1⋯N1	0.82	1.91	2.629 (4)	145
C19—H19A⋯Cg3i	0.97	2.96	3.795 (5)	144

Symmetry code: (i) . Cg3 is the centroid of the C10–C15 ring.