(1Z,1′Z,3E,3′E)-1,1′-Diphenyl-3,3′-[(1S,2S)-cyclo­hexane-1,2-diyldinitrilo]dibut-1-en-1-ol

Li, X.-Z.; Qu, Z.-R.

doi:10.1107/S1600536808014670

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1121

doi:10.1107/S1600536808014670

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(1Z,1′Z,3E,3′E)-1,1′-Diphenyl-3,3′-[(1S,2S)-cyclohexane-1,2-diyldinitrilo]dibut-1-en-1-ol

Xiu-Zhi Li ^a and Zhi-Rong Qu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: quzr@seu.edu.cn

(Received 29 April 2008; accepted 15 May 2008; online 21 May 2008)

A new tetradentate chiral Schiff base ligand, C₂₆H₃₀N₂O₂, has been synthesized by the reaction of 1-phenylbutane-1,3-dione with (1S,2S)-(−)-1,2-diaminocyclohexane. The chiral centers in the molecule have the same S configuration, since the absolute configuration was determined by that of the starting reagent (1S,2S)-(−)-1,2-diaminohexane. The cyclohexane ring is in a chair conformation, and the substituents are equatorial in the most stable conformation (trans-cyclohexyl). The crystal structure is stabilized by two intramolecular O—H⋯N hydrogen bonds and a weak C—H⋯π interaction.

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_r = 402.52
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.159
S = 1.07
2683 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ . Cg3 is the centroid of the C10–C15 ring.

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.

Supporting information

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

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

checkCIF report

Comment top

In recent years, research on Schiff bases has been intensified for the reason that some of them can form materials with non-linear optical (NLO) activity (Alemi & Shaabani, 2000), and some can be used for the asymmetric oxidation of methyl phenyl sulfides (Sasaki et al., 1991). The search for new chiral ligands for asymmetric synthesis is an important task in organic chemistry. Various chiral Schiff bases are widely used in asymmetric reactions (Jiang et al., 1995; Belokon et al., 1997; Bandini et al., 1999, 2000; Kureshy et al., 2001; Cozzi, 2003). Herein, we report the synthesis and crystal structure of a new chiral Schiff base ligand (1Z,1'Z,3E,3'E)-3,3'-((1S,2S)-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene))bis(1-phenylbut-1-en-1-ol). Fig. 1 show, the absolute configurations of the chiral centers and they have the same chirality (S-configuration). The cyclohexane ring is of chair conformation, and the substituents are equatorial in the most stable conformation of trans-cyclohexyl. The crystal structure is stabilized by two intramolecular O—H···N hydrogen bonds and a weak C—H···π interaction (Table 1).

Related literature top

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). Cg3 is the centroid of the C10–C15 ring.

Experimental top

1-phenylbutane-1,3-dione (3.89 g, 0.024 mol) in 6 ml of chloroform was added dropwise to a solution of chloroform (20 ml) containing (1S, 2S)-(–)-1,2-diaminocyclohexane (1.14 g, 0.01 mol), which was kept at 0–5°C with vigorous stirring during the reaction. After complete addition which took approximately 30 min, the mixture was stirred for another 1 h at room temperature. After the evaporation of the solvent under reduced pressure, the crude product was recrystallized by slowly evaporating with petroleum ether to yield colorless crystals.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

(1Z,1'Z,3E,3'E)-1,1'-Diphenyl-3,3'- [(1S,2S)-cyclohexane-1,2-diyldinitrilo]dibut-1-en-1-ol top

Crystal data top

C₂₆H₃₀N₂O₂	F(000) = 864
M_r = 402.52	D_x = 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 = 3.1–27.5°
b = 10.1205 (13) Å	µ = 0.07 mm⁻¹
c = 26.476 (3) Å	T = 293 K
V = 2386.7 (5) Å³	Block, colorless
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	2683 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 13.6612 pixels mm^-1	θ_max = 26.0°, θ_min = 2.4°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.980, T_max = 0.990	l = −32→32
22130 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0753P)² + 0.2595P] where P = (F_o² + 2F_c²)/3
2683 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₆H₃₀N₂O₂	V = 2386.7 (5) Å³
M_r = 402.52	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.9073 (11) Å	µ = 0.07 mm⁻¹
b = 10.1205 (13) Å	T = 293 K
c = 26.476 (3) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	2683 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1952 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.062
22130 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.07	Δρ_max = 0.29 e Å⁻³
2683 reflections	Δρ_min = −0.17 e Å⁻³
275 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₀N₂O₂
M_r	402.52
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.9073 (11), 10.1205 (13), 26.476 (3)
V (Å³)	2386.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	22130, 2683, 1952
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.159, 1.07
No. of reflections	2683
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.17

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, −z.

Acknowledgements

This work was supported by a Start-up Grant from Southeast University to ZRQ.

References

Alemi, A. A. & Shaabani, B. (2000). Acta Chim. Slov. 47, 363–369. CAS Google Scholar
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Belokon, Y., Flego, M., Ikonnikov, N., Moscalenko, M., North, M., Orizu, C., Tararov, V. & Tasinazzo, M. (1997). J. Chem. Soc. Perkin Trans. 1, pp. 1293–1295. CrossRef Web of Science Google Scholar
Cozzi, P. G. (2003). Angew. Chem. Int. Ed. 42, 2895–2898. Web of Science CrossRef CAS Google Scholar
Jiang, Y., Zhou, X., Hu, W., Wu, L. & Mi, A. (1995). Tetrahedron Asymmetry, 6, 405–408. CrossRef CAS Web of Science Google Scholar
Kureshy, R. I., Khan, N. H., Abdi, S. H. R., Patel, S. T. & Jasra, R. V. (2001). Tetrahedron Lett. 42, 2915–2918. Web of Science CrossRef CAS Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(1Z,1′Z,3E,3′E)-1,1′-Di­phenyl-3,3′-[(1S,2S)-cyclo­hexane-1,2-diyldi­nitrilo]dibut-1-en-1-ol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1Z,1′Z,3E,3′E)-1,1′-Diphenyl-3,3′-[(1S,2S)-cyclohexane-1,2-diyldinitrilo]dibut-1-en-1-ol