2,2′-[1,1′-(Propane-1,3-diyldioxy­dinitrilo)diethyl­idyne]di-1-naphthol

Dong, W.-K.; Wu, J.-C.; Sun, Y.-X.; Li, L.; Yao, J.

doi:10.1107/S1600536809023241

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1657

doi:10.1107/S1600536809023241

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2,2′-[1,1′-(Propane-1,3-diyldioxydinitrilo)diethylidyne]di-1-naphthol

Wen-Kui Dong,^a ^* Jian-Chao Wu,^a Yin-Xia Sun,^a Li Li ^a and Jian Yao ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 13 June 2009; accepted 17 June 2009; online 20 June 2009)

The molecule of the title compound, C₂₇H₂₆N₂O₄, lies across a crystallographic inversion centre and adopts an L-shaped configuration. Within the molecule, the two naphthalene units are approximately perpendicular, making a dihedral angle of 80.24 (5)°. The two intramolecular O—H⋯N hydrogen bonds, generate S(6) ring motifs. In the crystal structure, every molecule links five other molecules into an infinite cross-linked layered supramolecular structure via intermolecular C—H⋯O hydrogen bonds, C—H⋯π interactions and π–π stacking interactions [centroid–centroid distance = 3.956 (4) Å].

Related literature

For the steric and electronic properties of Schiff bases, see: Yamada (1999 ). For background to this study, see: Dong et al. (2006 ). For related structures, see: Dong & Duan (2008 ); Dong et al. (2008a ,b ,c ,d ); Duan et al. (2007 ); He et al. (2008 ).

Experimental

Crystal data

C₂₇H₂₆N₂O₄
M_r = 442.50
Triclinic, $[P \overline 1]$
a = 7.4411 (10) Å
b = 8.8911 (16) Å
c = 18.106 (2) Å
α = 100.645 (1)°
β = 94.331 (1)°
γ = 106.329 (2)°
V = 1119.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.42 × 0.37 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.957, T_max = 0.968
5800 measured reflections
3876 independent reflections
2325 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.145
S = 1.04
3876 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1	0.82	1.83	2.543 (2)	145
O4—H4⋯N2	0.82	1.82	2.540 (2)	146
C12—H12⋯O3ⁱ	0.93	2.68	3.588 (3)	166
C1—H1B⋯Cg1ⁱⁱ	0.97	2.78	3.480 (2)	129
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z+1. Cg1 is the centroid of the C6–C15 ring.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023241/hg2527sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023241/hg2527Isup2.hkl

checkCIF report

Comment top

Schiff bases are compounds containing the azomethine group, –R,R'C=N, prepared by the condensation reaction of a primary amine with active carbonyl group. Due to the versatility of their steric and electronic properties (Yamada, 1999), which can be fine tuned by choosing the appropriate amine and the substituents on an aromatic ring of the carbonyl compound, Schiff base bisoxime compounds have gained increased interest in the field of coordination chemistry (Dong et al., 2008a; He et al., 2008). As a part of our ongoing research (Dong et al., 2006; Duan et al., 2007), the synthesis and crystal structure of the title compound was reported (Fig. 1).

The molecule of the title compound lies across a crystallographic inversion centre (symmetry code: -x, -y, -z) and adopts an L-shaped configuration. This structure is not similar to what was observed in our previously reported series oxime compounds containing four-methene bridge, which always adopt a V-shaped configurations (Dong et al., 2006; Duan et al., 2007; Dong et al., 2008a; Dong & Duan, 2008; Dong et al., 2008b; Dong et al., 2008d; Dong et al., 2008c; He et al., 2008). Within the molecule, the dihedral angle between the plane of oxime functional groups and naphthalene ring is 8.93 (3)° for C6—C15 ring and O1—N1—C5, 5.30 (3)° for C18—C27 ring and O2—N2—C17, respectively. And the two naphthalene units are approximately vertical with the dihedral angle of 80.24 (5)°. The two intramolecular hydrogen bonds, O3—H3···N1 and O4—H4···N2,generate S(6) ring motifs helping to the stabilization of the title molecule.

In the crystal structure, the crystals are held together by an intermolecular C—H···π interaction and C12—H12···O3 hydrogen bonds between the phenolic-oxygen atom and the hydrogen of the naphthalene ring, in which the C1—H1B···π centroid separations are equal 2.782 Å involving the naphthalene ring C6—C15 (centroid, Cg1). In addition, the adjacent aromatic rings are further linked by the intermolecular π–π stacking interactions [centroid-to-centroid distance = 3.596 (4) Å]. Thus, every title compound molecule links five other molecules into an infinite crosslinked layer supramolecular structure via intermolecular C—H···O hydrogen bonds, C—H···π and π–π stacking interactions (Fig. 2).

Related literature top

For the steric and electronic properties of Schiff bases, see: Yamada (1999). For background to this strudy, see: Dong et al. (2006). For related structures, see: Dong & Duan (2008); Dong et al. (2008a,b,c,d); Duan et al. (2007); He et al. (2008). Cg1 is the centroid of the C6–C15 ring.

Experimental top

2,2'-[(Propane-1,3-diyldioxy)bis(nitriloethylidyne)]dinaphthol was synthesized according to an analogous method reported earlier (Dong et al., 2008 e). To an ethanol solution (5 ml) of 2-acetyl-1-naphthol (388.5 mg, 2.06 mmol) was added dropwise an ethanol solution (3 ml) of 1,3-bis(aminooxy)propane (109.7 mg, 1.03 mmol). The mixture solution was stirred at 328–333 K for 72 h. After cooling to room temperature, the precipitate was filtered off, and washed successively three times with ethanol. The product was dried in vacuo and purified by recrystallization from ethanol to yield 320.4 mg (Yield, 70.0%) of powder; m.p. 439–441 K. Colorless block-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a solution of ethyl acetate of 2,2'-[(propane-1,3-diyldioxy)bis(nitriloethylidyne)]dinaphthol at room temperature for about one month. Anal. Calcd. for C₂₇H₂₆N₂O₄: C, 73.28; H, 5.92; N, 6.33; Found: C, 73.25; H, 5.97; N, 6.29.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atom numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. Part of the supramolecular structure of the title compound. intra- and intermolecular hydrogen bonds, C—H···π interaction and π–π stacking interactions are shown as dashed lines.

2,2'-[1,1'-(Propane-1,3-diyldioxydinitrilo)diethylidyne]di-1-naphthol top

Crystal data top

C₂₇H₂₆N₂O₄	Z = 2
M_r = 442.50	F(000) = 468
Triclinic, P1	D_x = 1.313 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4411 (10) Å	Cell parameters from 1962 reflections
b = 8.8911 (16) Å	θ = 2.3–26.3°
c = 18.106 (2) Å	µ = 0.09 mm⁻¹
α = 100.645 (1)°	T = 298 K
β = 94.331 (1)°	Block-like, colorless
γ = 106.329 (2)°	0.50 × 0.42 × 0.37 mm
V = 1119.4 (3) Å³

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3876 independent reflections
Radiation source: fine-focus sealed tube	2325 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→8
T_min = 0.957, T_max = 0.968	k = −10→10
5800 measured reflections	l = −20→21

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0669P)² + 0.1652P] where P = (F_o² + 2F_c²)/3
3876 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₇H₂₆N₂O₄	γ = 106.329 (2)°
M_r = 442.50	V = 1119.4 (3) Å³
Triclinic, P1	Z = 2
a = 7.4411 (10) Å	Mo Kα radiation
b = 8.8911 (16) Å	µ = 0.09 mm⁻¹
c = 18.106 (2) Å	T = 298 K
α = 100.645 (1)°	0.50 × 0.42 × 0.37 mm
β = 94.331 (1)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3876 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2325 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.968	R_int = 0.025
5800 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
3876 reflections	Δρ_min = −0.22 e Å⁻³
298 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
N1	0.4304 (3)	0.3291 (2)	0.39356 (10)	0.0472 (5)
N2	0.5352 (3)	0.4359 (2)	0.09736 (10)	0.0490 (5)
O1	0.3227 (2)	0.35088 (19)	0.33130 (9)	0.0531 (5)
O2	0.6102 (2)	0.55995 (19)	0.16190 (9)	0.0568 (5)
O3	0.7381 (2)	0.38979 (19)	0.48069 (9)	0.0567 (5)
H3	0.6693	0.3990	0.4453	0.085*
O4	0.2690 (2)	0.2606 (2)	−0.00541 (9)	0.0589 (5)
H4	0.3176	0.3292	0.0332	0.088*
C1	0.4460 (3)	0.4646 (3)	0.29743 (12)	0.0444 (6)
H1A	0.5504	0.4264	0.2822	0.053*
H1B	0.4971	0.5663	0.3336	0.053*
C2	0.3361 (3)	0.4864 (3)	0.22958 (12)	0.0494 (6)
H2A	0.2300	0.5216	0.2451	0.059*
H2B	0.2864	0.3843	0.1936	0.059*
C3	0.4578 (4)	0.6083 (3)	0.19140 (13)	0.0557 (7)
H3A	0.3795	0.6253	0.1503	0.067*
H3B	0.5088	0.7097	0.2278	0.067*
C4	0.1200 (3)	0.1930 (3)	0.42415 (14)	0.0608 (7)
H4A	0.0746	0.2444	0.3878	0.091*
H4B	0.0718	0.2184	0.4710	0.091*
H4C	0.0779	0.0789	0.4052	0.091*
C5	0.3322 (3)	0.2511 (2)	0.43736 (12)	0.0421 (5)
C6	0.6336 (3)	0.2932 (2)	0.52118 (12)	0.0409 (5)
C7	0.4391 (3)	0.2236 (2)	0.50250 (11)	0.0385 (5)
C8	0.3456 (3)	0.1201 (3)	0.54803 (13)	0.0488 (6)
H8	0.2156	0.0725	0.5366	0.059*
C9	0.4393 (4)	0.0885 (3)	0.60760 (13)	0.0510 (6)
H9	0.3730	0.0189	0.6356	0.061*
C10	0.6365 (3)	0.1598 (3)	0.62776 (12)	0.0445 (6)
C11	0.7339 (3)	0.2654 (2)	0.58449 (12)	0.0413 (5)
C12	0.9311 (3)	0.3417 (3)	0.60585 (14)	0.0552 (7)
H12	0.9972	0.4118	0.5781	0.066*
C13	1.0230 (4)	0.3126 (3)	0.66666 (16)	0.0673 (8)
H13	1.1520	0.3636	0.6803	0.081*
C14	0.9279 (4)	0.2076 (3)	0.70901 (16)	0.0667 (8)
H14	0.9933	0.1888	0.7504	0.080*
C15	0.7397 (4)	0.1326 (3)	0.69001 (14)	0.0585 (7)
H15	0.6777	0.0621	0.7185	0.070*
C16	0.8658 (4)	0.4430 (3)	0.09754 (15)	0.0681 (8)
H16A	0.8829	0.5187	0.1447	0.102*
H16B	0.9350	0.4952	0.0620	0.102*
H16C	0.9112	0.3557	0.1058	0.102*
C17	0.6600 (3)	0.3798 (3)	0.06659 (12)	0.0449 (6)
C18	0.4008 (3)	0.1992 (3)	−0.03454 (12)	0.0419 (5)
C19	0.5894 (3)	0.2506 (3)	−0.00192 (12)	0.0419 (5)
C20	0.7126 (3)	0.1727 (3)	−0.03704 (14)	0.0518 (6)
H20	0.8390	0.2047	−0.0161	0.062*
C21	0.6529 (3)	0.0533 (3)	−0.10000 (14)	0.0552 (6)
H21	0.7382	0.0044	−0.1209	0.066*
C22	0.4635 (3)	0.0022 (3)	−0.13423 (13)	0.0460 (6)
C23	0.3358 (3)	0.0756 (3)	−0.10137 (12)	0.0422 (5)
C24	0.1464 (4)	0.0254 (3)	−0.13600 (14)	0.0582 (7)
H24	0.0612	0.0739	−0.1147	0.070*
C25	0.0862 (4)	−0.0921 (3)	−0.19974 (16)	0.0677 (8)
H25	−0.0393	−0.1237	−0.2217	0.081*
C26	0.2131 (4)	−0.1659 (3)	−0.23247 (15)	0.0669 (8)
H26	0.1715	−0.2467	−0.2761	0.080*
C27	0.3962 (4)	−0.1200 (3)	−0.20072 (14)	0.0604 (7)
H27	0.4792	−0.1697	−0.2231	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0453 (12)	0.0502 (11)	0.0435 (11)	0.0087 (9)	0.0039 (9)	0.0134 (9)
N2	0.0551 (13)	0.0511 (12)	0.0396 (11)	0.0148 (10)	0.0066 (10)	0.0086 (9)
O1	0.0478 (10)	0.0605 (10)	0.0468 (9)	0.0058 (8)	0.0015 (8)	0.0198 (8)
O2	0.0626 (11)	0.0590 (11)	0.0434 (10)	0.0119 (9)	0.0087 (8)	0.0069 (8)
O3	0.0413 (9)	0.0685 (11)	0.0573 (10)	0.0017 (8)	0.0116 (8)	0.0277 (9)
O4	0.0453 (10)	0.0706 (12)	0.0605 (11)	0.0237 (9)	0.0085 (8)	0.0031 (9)
C1	0.0471 (14)	0.0396 (12)	0.0447 (13)	0.0090 (11)	0.0113 (11)	0.0087 (10)
C2	0.0585 (16)	0.0495 (14)	0.0412 (13)	0.0188 (12)	0.0078 (11)	0.0081 (11)
C3	0.0747 (19)	0.0512 (15)	0.0442 (14)	0.0223 (13)	0.0116 (13)	0.0113 (11)
C4	0.0441 (15)	0.0763 (18)	0.0544 (16)	0.0052 (13)	0.0058 (12)	0.0158 (14)
C5	0.0420 (13)	0.0375 (12)	0.0426 (13)	0.0075 (10)	0.0103 (11)	0.0034 (10)
C6	0.0445 (13)	0.0351 (12)	0.0408 (13)	0.0067 (10)	0.0145 (11)	0.0071 (10)
C7	0.0403 (13)	0.0343 (11)	0.0376 (12)	0.0070 (10)	0.0084 (10)	0.0053 (9)
C8	0.0430 (13)	0.0431 (13)	0.0539 (15)	0.0020 (11)	0.0112 (12)	0.0102 (11)
C9	0.0600 (16)	0.0413 (13)	0.0504 (15)	0.0067 (12)	0.0157 (13)	0.0164 (11)
C10	0.0529 (15)	0.0363 (12)	0.0448 (14)	0.0150 (11)	0.0103 (12)	0.0054 (10)
C11	0.0424 (13)	0.0393 (12)	0.0417 (13)	0.0127 (10)	0.0088 (10)	0.0052 (10)
C12	0.0428 (14)	0.0619 (16)	0.0589 (16)	0.0134 (12)	0.0089 (12)	0.0107 (13)
C13	0.0509 (16)	0.0782 (19)	0.0696 (19)	0.0214 (14)	−0.0028 (14)	0.0092 (16)
C14	0.076 (2)	0.0709 (18)	0.0596 (17)	0.0337 (16)	−0.0010 (15)	0.0152 (14)
C15	0.0749 (19)	0.0511 (15)	0.0553 (16)	0.0245 (14)	0.0129 (14)	0.0161 (12)
C16	0.0544 (17)	0.083 (2)	0.0582 (17)	0.0127 (14)	0.0003 (13)	0.0089 (14)
C17	0.0450 (14)	0.0517 (14)	0.0406 (13)	0.0115 (11)	0.0052 (11)	0.0213 (11)
C18	0.0390 (13)	0.0483 (13)	0.0447 (13)	0.0163 (11)	0.0123 (11)	0.0180 (11)
C19	0.0415 (13)	0.0496 (13)	0.0389 (13)	0.0142 (11)	0.0081 (10)	0.0187 (10)
C20	0.0400 (14)	0.0594 (16)	0.0589 (16)	0.0165 (12)	0.0073 (12)	0.0170 (13)
C21	0.0497 (16)	0.0591 (16)	0.0639 (17)	0.0251 (13)	0.0170 (13)	0.0137 (13)
C22	0.0502 (15)	0.0424 (13)	0.0500 (14)	0.0145 (11)	0.0118 (12)	0.0182 (11)
C23	0.0428 (13)	0.0426 (13)	0.0447 (13)	0.0129 (10)	0.0072 (11)	0.0175 (10)
C24	0.0511 (16)	0.0580 (16)	0.0629 (17)	0.0149 (13)	0.0031 (13)	0.0110 (13)
C25	0.0582 (17)	0.0597 (17)	0.074 (2)	0.0070 (14)	−0.0095 (15)	0.0113 (15)
C26	0.083 (2)	0.0475 (15)	0.0576 (17)	0.0083 (15)	−0.0031 (16)	0.0039 (13)
C27	0.074 (2)	0.0469 (15)	0.0600 (17)	0.0194 (14)	0.0116 (15)	0.0090 (12)

Geometric parameters (Å, º) top

N1—C5	1.284 (3)	C10—C11	1.413 (3)
N1—O1	1.408 (2)	C11—C12	1.422 (3)
N2—C17	1.287 (3)	C12—C13	1.356 (3)
N2—O2	1.404 (2)	C12—H12	0.9300
O1—C1	1.426 (2)	C13—C14	1.391 (4)
O2—C3	1.427 (3)	C13—H13	0.9300
O3—C6	1.350 (2)	C14—C15	1.357 (4)
O3—H3	0.8200	C14—H14	0.9300
O4—C18	1.345 (3)	C15—H15	0.9300
O4—H4	0.8200	C16—C17	1.498 (3)
C1—C2	1.497 (3)	C16—H16A	0.9600
C1—H1A	0.9700	C16—H16B	0.9600
C1—H1B	0.9700	C16—H16C	0.9600
C2—C3	1.514 (3)	C17—C19	1.473 (3)
C2—H2A	0.9700	C18—C19	1.393 (3)
C2—H2B	0.9700	C18—C23	1.424 (3)
C3—H3A	0.9700	C19—C20	1.417 (3)
C3—H3B	0.9700	C20—C21	1.355 (3)
C4—C5	1.502 (3)	C20—H20	0.9300
C4—H4A	0.9600	C21—C22	1.408 (3)
C4—H4B	0.9600	C21—H21	0.9300
C4—H4C	0.9600	C22—C23	1.405 (3)
C5—C7	1.469 (3)	C22—C27	1.414 (3)
C6—C7	1.392 (3)	C23—C24	1.410 (3)
C6—C11	1.418 (3)	C24—C25	1.356 (3)
C7—C8	1.420 (3)	C24—H24	0.9300
C8—C9	1.356 (3)	C25—C26	1.401 (4)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.414 (3)	C26—C27	1.355 (4)
C9—H9	0.9300	C26—H26	0.9300
C10—C15	1.412 (3)	C27—H27	0.9300

C5—N1—O1	114.40 (18)	C13—C12—C11	120.2 (2)
C17—N2—O2	113.84 (19)	C13—C12—H12	119.9
N1—O1—C1	107.51 (15)	C11—C12—H12	119.9
N2—O2—C3	108.21 (17)	C12—C13—C14	121.1 (3)
C6—O3—H3	109.5	C12—C13—H13	119.4
C18—O4—H4	109.5	C14—C13—H13	119.4
O1—C1—C2	108.60 (18)	C15—C14—C13	120.1 (3)
O1—C1—H1A	110.0	C15—C14—H14	119.9
C2—C1—H1A	110.0	C13—C14—H14	119.9
O1—C1—H1B	110.0	C14—C15—C10	121.1 (2)
C2—C1—H1B	110.0	C14—C15—H15	119.4
H1A—C1—H1B	108.4	C10—C15—H15	119.4
C1—C2—C3	111.5 (2)	C17—C16—H16A	109.5
C1—C2—H2A	109.3	C17—C16—H16B	109.5
C3—C2—H2A	109.3	H16A—C16—H16B	109.5
C1—C2—H2B	109.3	C17—C16—H16C	109.5
C3—C2—H2B	109.3	H16A—C16—H16C	109.5
H2A—C2—H2B	108.0	H16B—C16—H16C	109.5
O2—C3—C2	112.91 (19)	N2—C17—C19	116.1 (2)
O2—C3—H3A	109.0	N2—C17—C16	122.3 (2)
C2—C3—H3A	109.0	C19—C17—C16	121.5 (2)
O2—C3—H3B	109.0	O4—C18—C19	123.0 (2)
C2—C3—H3B	109.0	O4—C18—C23	115.8 (2)
H3A—C3—H3B	107.8	C19—C18—C23	121.2 (2)
C5—C4—H4A	109.5	C18—C19—C20	117.3 (2)
C5—C4—H4B	109.5	C18—C19—C17	122.1 (2)
H4A—C4—H4B	109.5	C20—C19—C17	120.6 (2)
C5—C4—H4C	109.5	C21—C20—C19	122.4 (2)
H4A—C4—H4C	109.5	C21—C20—H20	118.8
H4B—C4—H4C	109.5	C19—C20—H20	118.8
N1—C5—C7	116.2 (2)	C20—C21—C22	120.9 (2)
N1—C5—C4	122.4 (2)	C20—C21—H21	119.6
C7—C5—C4	121.34 (19)	C22—C21—H21	119.6
O3—C6—C7	122.7 (2)	C23—C22—C21	118.9 (2)
O3—C6—C11	116.03 (19)	C23—C22—C27	118.5 (2)
C7—C6—C11	121.28 (19)	C21—C22—C27	122.6 (2)
C6—C7—C8	117.5 (2)	C22—C23—C24	118.9 (2)
C6—C7—C5	122.24 (19)	C22—C23—C18	119.4 (2)
C8—C7—C5	120.3 (2)	C24—C23—C18	121.7 (2)
C9—C8—C7	122.2 (2)	C25—C24—C23	121.2 (3)
C9—C8—H8	118.9	C25—C24—H24	119.4
C7—C8—H8	118.9	C23—C24—H24	119.4
C8—C9—C10	120.9 (2)	C24—C25—C26	120.0 (3)
C8—C9—H9	119.5	C24—C25—H25	120.0
C10—C9—H9	119.5	C26—C25—H25	120.0
C15—C10—C11	118.6 (2)	C27—C26—C25	120.2 (2)
C15—C10—C9	123.0 (2)	C27—C26—H26	119.9
C11—C10—C9	118.4 (2)	C25—C26—H26	119.9
C10—C11—C6	119.6 (2)	C26—C27—C22	121.2 (3)
C10—C11—C12	118.8 (2)	C26—C27—H27	119.4
C6—C11—C12	121.6 (2)	C22—C27—H27	119.4

C5—N1—O1—C1	168.65 (19)	C13—C14—C15—C10	−0.5 (4)
C17—N2—O2—C3	−178.59 (18)	C11—C10—C15—C14	1.0 (4)
N1—O1—C1—C2	178.37 (17)	C9—C10—C15—C14	−177.7 (2)
O1—C1—C2—C3	178.99 (18)	O2—N2—C17—C19	−179.28 (16)
N2—O2—C3—C2	72.6 (2)	O2—N2—C17—C16	−0.2 (3)
C1—C2—C3—O2	63.2 (3)	O4—C18—C19—C20	178.18 (19)
O1—N1—C5—C7	179.14 (16)	C23—C18—C19—C20	−1.3 (3)
O1—N1—C5—C4	−1.8 (3)	O4—C18—C19—C17	−1.4 (3)
O3—C6—C7—C8	178.1 (2)	C23—C18—C19—C17	179.14 (19)
C11—C6—C7—C8	−1.7 (3)	N2—C17—C19—C18	4.1 (3)
O3—C6—C7—C5	−0.5 (3)	C16—C17—C19—C18	−175.1 (2)
C11—C6—C7—C5	179.8 (2)	N2—C17—C19—C20	−175.5 (2)
N1—C5—C7—C6	7.2 (3)	C16—C17—C19—C20	5.4 (3)
C4—C5—C7—C6	−171.8 (2)	C18—C19—C20—C21	0.3 (3)
N1—C5—C7—C8	−171.3 (2)	C17—C19—C20—C21	179.9 (2)
C4—C5—C7—C8	9.7 (3)	C19—C20—C21—C22	0.8 (4)
C6—C7—C8—C9	−0.1 (3)	C20—C21—C22—C23	−0.9 (3)
C5—C7—C8—C9	178.5 (2)	C20—C21—C22—C27	178.8 (2)
C7—C8—C9—C10	0.8 (4)	C21—C22—C23—C24	179.4 (2)
C8—C9—C10—C15	178.9 (2)	C27—C22—C23—C24	−0.3 (3)
C8—C9—C10—C11	0.2 (3)	C21—C22—C23—C18	−0.1 (3)
C15—C10—C11—C6	179.3 (2)	C27—C22—C23—C18	−179.8 (2)
C9—C10—C11—C6	−1.9 (3)	O4—C18—C23—C22	−178.33 (19)
C15—C10—C11—C12	−0.8 (3)	C19—C18—C23—C22	1.2 (3)
C9—C10—C11—C12	178.0 (2)	O4—C18—C23—C24	2.2 (3)
O3—C6—C11—C10	−177.05 (19)	C19—C18—C23—C24	−178.3 (2)
C7—C6—C11—C10	2.7 (3)	C22—C23—C24—C25	0.3 (3)
O3—C6—C11—C12	3.1 (3)	C18—C23—C24—C25	179.8 (2)
C7—C6—C11—C12	−177.2 (2)	C23—C24—C25—C26	−0.1 (4)
C10—C11—C12—C13	0.2 (3)	C24—C25—C26—C27	−0.1 (4)
C6—C11—C12—C13	−179.9 (2)	C25—C26—C27—C22	0.2 (4)
C11—C12—C13—C14	0.3 (4)	C23—C22—C27—C26	0.1 (3)
C12—C13—C14—C15	−0.2 (4)	C21—C22—C27—C26	−179.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	1.83	2.543 (2)	145
O4—H4···N2	0.82	1.82	2.540 (2)	146
C12—H12···O3ⁱ	0.93	2.68	3.588 (3)	166
C1—H1B···Cg1ⁱⁱ	0.97	2.78	3.480 (2)	129

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₆N₂O₄
M_r	442.50
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.4411 (10), 8.8911 (16), 18.106 (2)
α, β, γ (°)	100.645 (1), 94.331 (1), 106.329 (2)
V (Å³)	1119.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.42 × 0.37

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.957, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	5800, 3876, 2325
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.145, 1.04
No. of reflections	3876
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
O3—H3···N1	0.82	1.83	2.543 (2)	145.2
O4—H4···N2	0.82	1.82	2.540 (2)	145.6
C12—H12···O3ⁱ	0.93	2.68	3.588 (3)	165.8
C1—H1B···Cg1ⁱⁱ	0.970	2.782	3.480 (2)	129.41

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

Acknowledgements

The authors acknowledge finanicial support from the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University.

References

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