(−)-Dimethyl 3,3′-diphenyl-2,2′-[pyridine-2,6-diylbis(carbonyl­imino)]dipropanoate

Yin, S.; Cui, Y.; Xia, G.; Zhang, Y.; Sun, G.

doi:10.1107/S1600536809023721

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1713

doi:10.1107/S1600536809023721

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(−)-Dimethyl 3,3′-diphenyl-2,2′-[pyridine-2,6-diylbis(carbonylimino)]dipropanoate

Shaohong Yin,^a Yu Cui,^a Guangming Xia,^a Yanju Zhang ^a and Guoxin Sun ^a ^*

^aSchool of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, People's Republic of China
^*Correspondence e-mail: chm_sungx@ujn.edu.cn

(Received 14 June 2009; accepted 20 June 2009; online 27 June 2009)

The title compound, C₂₇H₂₇N₃O₆, a bis-amide derivative, is also a chiral amino acid ester with L-phenylalanine methyl ester groups as amine substituents. The pyridine ring is oriented at dihedral angles of 89.69 (3) and 62.95 (3)° with respect to the phenyl rings, while the dihedral angle between the phenyl rings is 60.76 (3)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains. One of the carbonyl O atoms and one of the methoxy CH₃ groups are disordered over two positions. The O atom was refined with occupancies of 0.69 (13) and 0.31 (13), while C and H atoms were refined with occupancies of 0.69 (8) and 0.31 (8).

Related literature

For general background, see: Darshan et al. (1998 ). For related structures, see: Amr et al. (1999 ); Moriuchi et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₇H₂₇N₃O₆
M_r = 489.52
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1549 (11) Å
b = 9.9319 (12) Å
c = 27.83 (2) Å
V = 2530 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.15 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.986, T_max = 0.991
12674 measured reflections
2650 independent reflections
1929 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.134
S = 1.05
2650 reflections
349 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.86	2.37	3.178 (4)	157
N3—H3⋯O1ⁱ	0.86	2.40	3.190 (4)	154
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXS97 (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/S1600536809023721/hk2713sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023721/hk2713Isup2.hkl

checkCIF report

Comment top

The chiral bisamide derived from pyridine-2,6-dicarboxylic acid and natural amino acids adopts spontaneously relatively rigid conformation reinforced by bifurcated hydrogen bonding between NH of carboxamides at positions 2 and 6 of the pyridine nucleus and its nitrogen (Darshan et al., 1998). This finding makes this kind of structures very promising for biological activities and as precursors in the syntheses of various compounds.

In the structure of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N1/C2-C6), B (C11-C16) and C (C21-C26) are, of course, planar and the dihedral angles between them are A/B = 89.69 (3), A/C = 62.95 (3) and B/C = 60.76 (3)°, respectively. The absolute configuration was determined by comparison with Amr et al. (1999) and according to the known S configuration at the C atom to which the benzyl group is attached. Both of C9 and C19 are chiral atoms in the structure. The pyridine-2,6-dicarboxamide core approximates C₂ point symmetry. Such a feature seems to be common for symmetrically substituted pyridine-2,6-dicarboxamide derivatives.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains, in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Darshan et al. (1998). For related structures, see: Amr et al. (1999); Moriuchi et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by a slight modification of the literature method (Moriuchi et al., 2006). To a stirred mixture of L-phenylalanine methyl ester hydrochloride (129.4 mg, 0.6 mmol) in dry dichloromethane (15 ml) and triethylamine (0.21 ml, 1.5 mmol) was added dropwise 2,6-pyridyldicarbonyl dichloride (61.2 mg, 0.3 mmol) in dichloromethane (3 ml) at 273 K, and then stirred for 18 h at room temperature. The resulting mixture was diluted with dichloromethane, washed with saturated NaHCO₃ solution and brine, and then dried over anhydrous MgSO₄. The solvent was evaporated in vacuo. The title compound was isolated as a colorless solid by recrystallization from ethanol (yield; 117.5 mg, 80%; m.p. 403-404 K, enantiomeric excess >99%). Crystals suitable for X-ray analysis were obtained from the mixed solution of ethanol and diisopropyl ether by slow evaporation over a period of several days. C₂₇H₂₇N₃O₆: C 66.25, H 5.56, N 8.58%; found: C 66.11, H 5.46, N 8.64%. IR (KBr): v = 3398, 3333, 3028, 1745, 1678, 1523 cm^-1.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (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 molecule, with the atom-numbering scheme.

(-)-Dimethyl 3,3'-diphenyl-2,2'-[pyridine-2,6-diylbis(carbonylimino)]dipropanoate top

Crystal data top

C₂₇H₂₇N₃O₆	F(000) = 1032
M_r = 489.52	D_x = 1.285 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2406 reflections
a = 9.1549 (11) Å	θ = 2.3–20.1°
b = 9.9319 (12) Å	µ = 0.09 mm⁻¹
c = 27.83 (2) Å	T = 294 K
V = 2530 (2) Å³	Prism, colorless
Z = 4	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2650 independent reflections
Radiation source: fine-focus sealed tube	1929 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 25.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
T_min = 0.986, T_max = 0.991	k = −11→10
12674 measured reflections	l = −33→32

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1P)² + 0.1227P] where P = (F_o² + 2F_c²)/3
2650 reflections	(Δ/σ)_max = 0.001
349 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₇H₂₇N₃O₆	V = 2530 (2) Å³
M_r = 489.52	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.1549 (11) Å	µ = 0.09 mm⁻¹
b = 9.9319 (12) Å	T = 294 K
c = 27.83 (2) Å	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2650 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1929 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.991	R_int = 0.040
12674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	Δρ_max = 0.27 e Å⁻³
2650 reflections	Δρ_min = −0.20 e Å⁻³
349 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	Occ. (<1)
O1	0.2953 (3)	0.1251 (2)	−0.02271 (8)	0.0591 (6)
O2	0.6669 (3)	0.1803 (3)	0.19298 (10)	0.0826 (9)
O3	0.5457 (4)	0.3451 (4)	−0.13664 (12)	0.1087 (12)
O4	0.687 (6)	0.228 (3)	−0.0887 (8)	0.101 (8)	0.69 (13)
O4'	0.614 (14)	0.190 (8)	−0.0963 (17)	0.101 (18)	0.31 (13)
O5	0.5417 (3)	0.5103 (4)	0.17725 (10)	0.1148 (13)
O6	0.6902 (3)	0.4951 (4)	0.23889 (10)	0.0983 (11)
N1	0.5319 (3)	0.1704 (3)	0.07475 (9)	0.0469 (6)
N2	0.4923 (3)	0.2592 (3)	−0.01478 (9)	0.0536 (7)
H2	0.5678	0.2767	0.0025	0.064*
N3	0.7013 (3)	0.3214 (3)	0.13144 (10)	0.0529 (7)
H3	0.6951	0.3330	0.1009	0.063*
C1	0.4044 (3)	0.1610 (3)	−0.00050 (11)	0.0458 (8)
C2	0.4433 (3)	0.0987 (3)	0.04660 (11)	0.0471 (8)
C3	0.3850 (4)	−0.0227 (3)	0.06022 (14)	0.0580 (9)
H3A	0.3274	−0.0720	0.0391	0.070*
C4	0.4132 (4)	−0.0703 (4)	0.10552 (16)	0.0751 (12)
H4	0.3743	−0.1520	0.1156	0.090*
C5	0.4999 (4)	0.0044 (4)	0.13576 (14)	0.0686 (10)
H5	0.5191	−0.0246	0.1669	0.082*
C6	0.5579 (4)	0.1239 (3)	0.11873 (12)	0.0522 (8)
C7	0.6480 (4)	0.2102 (4)	0.15113 (13)	0.0556 (9)
C8	0.5704 (5)	0.2909 (4)	−0.09640 (15)	0.0655 (11)
C9	0.4695 (4)	0.3387 (3)	−0.05746 (12)	0.0535 (8)
H9	0.3687	0.3254	−0.0683	0.064*
C10	0.4920 (4)	0.4888 (4)	−0.04709 (13)	0.0603 (9)
H10A	0.5885	0.5015	−0.0334	0.072*
H10B	0.4885	0.5379	−0.0772	0.072*
C11	0.3809 (4)	0.5473 (3)	−0.01345 (13)	0.0556 (9)
C12	0.2661 (5)	0.6211 (5)	−0.03059 (18)	0.0831 (13)
H12	0.2566	0.6349	−0.0635	0.100*
C13	0.1648 (5)	0.6748 (5)	0.0002 (3)	0.1036 (18)
H13	0.0881	0.7256	−0.0121	0.124*
C14	0.1745 (7)	0.6555 (6)	0.0479 (3)	0.111 (2)
H14	0.1050	0.6917	0.0685	0.133*
C15	0.2870 (9)	0.5825 (5)	0.0652 (2)	0.116 (2)
H15	0.2950	0.5683	0.0981	0.139*
C16	0.3896 (6)	0.5291 (5)	0.03496 (16)	0.0873 (14)
H16	0.4666	0.4796	0.0477	0.105*
C17	0.6428 (7)	0.3105 (6)	−0.17656 (16)	0.1132 (19)
H17A	0.6814	0.2216	−0.1717	0.170*
H17B	0.7218	0.3740	−0.1780	0.170*
H17C	0.5891	0.3131	−0.2062	0.170*
C18	0.6648 (4)	0.4771 (5)	0.19758 (15)	0.0697 (11)
C19	0.7696 (4)	0.4234 (4)	0.16093 (12)	0.0551 (9)
H19	0.8507	0.3809	0.1782	0.066*
C20	0.8326 (5)	0.5343 (4)	0.12987 (13)	0.0701 (11)
H20A	0.9090	0.4966	0.1098	0.084*
H20B	0.7565	0.5681	0.1088	0.084*
C21	0.8940 (4)	0.6484 (4)	0.15781 (13)	0.0634 (10)
C22	0.8182 (6)	0.7669 (4)	0.16388 (15)	0.0797 (12)
H22	0.7274	0.7766	0.1493	0.096*
C23	0.8722 (6)	0.8708 (5)	0.19077 (17)	0.0904 (14)
H23	0.8181	0.9494	0.1945	0.108*
C24	1.0036 (6)	0.8593 (5)	0.21183 (15)	0.0843 (13)
H24	1.0415	0.9304	0.2297	0.101*
C25	1.0805 (5)	0.7442 (5)	0.20703 (16)	0.0881 (14)
H25	1.1707	0.7355	0.2221	0.106*
C26	1.0258 (5)	0.6390 (5)	0.17983 (16)	0.0797 (12)
H26	1.0804	0.5605	0.1766	0.096*
C27	0.440 (2)	0.592 (5)	0.2070 (10)	0.135 (10)	0.69 (8)
H27A	0.3787	0.5336	0.2256	0.202*	0.69 (8)
H27B	0.3802	0.6469	0.1864	0.202*	0.69 (8)
H27C	0.4951	0.6491	0.2281	0.202*	0.69 (8)
C27'	0.425 (4)	0.506 (11)	0.220 (2)	0.135 (17)	0.31 (8)
H27D	0.4288	0.4196	0.2350	0.202*	0.31 (8)
H27E	0.3294	0.5207	0.2067	0.202*	0.31 (8)
H27F	0.4475	0.5751	0.2425	0.202*	0.31 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0541 (13)	0.0687 (15)	0.0544 (14)	−0.0128 (12)	−0.0117 (12)	−0.0002 (12)
O2	0.098 (2)	0.098 (2)	0.0523 (17)	−0.0263 (19)	−0.0149 (16)	0.0129 (15)
O3	0.130 (3)	0.128 (3)	0.068 (2)	0.034 (2)	0.019 (2)	0.033 (2)
O4	0.099 (18)	0.123 (9)	0.080 (5)	0.045 (11)	0.009 (7)	0.010 (5)
O4'	0.10 (4)	0.123 (19)	0.080 (11)	0.05 (2)	0.009 (16)	0.010 (11)
O5	0.077 (2)	0.192 (4)	0.076 (2)	0.046 (2)	−0.0100 (17)	−0.047 (2)
O6	0.099 (2)	0.141 (3)	0.0547 (17)	0.011 (2)	−0.0081 (17)	−0.0303 (18)
N1	0.0451 (14)	0.0508 (14)	0.0448 (16)	−0.0010 (13)	0.0018 (12)	0.0015 (12)
N2	0.0489 (14)	0.0586 (16)	0.0533 (17)	−0.0097 (14)	−0.0105 (13)	0.0049 (14)
N3	0.0620 (17)	0.0578 (17)	0.0389 (15)	−0.0040 (15)	−0.0052 (14)	−0.0047 (13)
C1	0.0412 (16)	0.0472 (17)	0.0491 (19)	0.0007 (15)	0.0007 (15)	−0.0056 (15)
C2	0.0454 (17)	0.0494 (18)	0.0466 (19)	0.0011 (15)	−0.0019 (15)	−0.0021 (15)
C3	0.055 (2)	0.051 (2)	0.068 (2)	−0.0062 (16)	−0.0075 (18)	0.0033 (18)
C4	0.076 (3)	0.062 (2)	0.088 (3)	−0.015 (2)	−0.011 (2)	0.020 (2)
C5	0.076 (2)	0.068 (2)	0.062 (2)	−0.009 (2)	−0.008 (2)	0.0157 (19)
C6	0.0499 (18)	0.0537 (19)	0.053 (2)	−0.0023 (16)	−0.0027 (16)	0.0035 (16)
C7	0.058 (2)	0.066 (2)	0.043 (2)	−0.0020 (18)	−0.0017 (17)	0.0023 (17)
C8	0.085 (3)	0.054 (2)	0.058 (3)	0.004 (2)	−0.002 (2)	0.0019 (19)
C9	0.0523 (19)	0.0548 (19)	0.053 (2)	−0.0071 (16)	−0.0062 (16)	0.0070 (17)
C10	0.059 (2)	0.059 (2)	0.063 (2)	−0.0070 (19)	−0.0017 (18)	0.0081 (18)
C11	0.058 (2)	0.0498 (19)	0.059 (2)	−0.0076 (16)	−0.0035 (18)	0.0008 (17)
C12	0.079 (3)	0.087 (3)	0.083 (3)	0.016 (3)	−0.014 (2)	−0.019 (2)
C13	0.067 (3)	0.096 (4)	0.147 (5)	0.013 (3)	−0.010 (3)	−0.043 (4)
C14	0.113 (4)	0.079 (4)	0.140 (6)	−0.025 (3)	0.051 (4)	−0.034 (4)
C15	0.189 (7)	0.075 (3)	0.083 (4)	−0.008 (4)	0.043 (4)	−0.005 (3)
C16	0.122 (4)	0.075 (3)	0.065 (3)	0.014 (3)	0.000 (3)	0.000 (2)
C17	0.162 (5)	0.111 (4)	0.067 (3)	−0.006 (4)	0.029 (3)	0.008 (3)
C18	0.058 (2)	0.096 (3)	0.055 (2)	0.002 (2)	−0.010 (2)	−0.011 (2)
C19	0.058 (2)	0.063 (2)	0.0443 (19)	−0.0005 (17)	−0.0054 (16)	−0.0081 (16)
C20	0.084 (3)	0.076 (3)	0.050 (2)	−0.016 (2)	−0.001 (2)	−0.0069 (19)
C21	0.074 (2)	0.068 (2)	0.048 (2)	−0.012 (2)	−0.0036 (18)	−0.0025 (18)
C22	0.095 (3)	0.070 (3)	0.074 (3)	−0.003 (2)	−0.027 (3)	0.003 (2)
C23	0.119 (4)	0.064 (3)	0.088 (3)	−0.004 (3)	−0.018 (3)	0.001 (2)
C24	0.108 (4)	0.068 (3)	0.076 (3)	−0.017 (3)	−0.014 (3)	−0.011 (2)
C25	0.077 (3)	0.099 (3)	0.088 (3)	−0.011 (3)	−0.018 (3)	−0.016 (3)
C26	0.070 (3)	0.081 (3)	0.087 (3)	−0.002 (2)	−0.003 (2)	−0.017 (2)
C27	0.091 (7)	0.21 (3)	0.107 (10)	0.071 (13)	0.013 (7)	−0.021 (13)
C27'	0.091 (15)	0.21 (5)	0.11 (2)	0.07 (3)	0.013 (15)	−0.02 (3)

Geometric parameters (Å, º) top

O1—C1	1.228 (4)	C12—C13	1.371 (7)
O2—C7	1.214 (4)	C12—H12	0.9300
O3—C8	1.263 (5)	C13—C14	1.343 (8)
O3—C17	1.464 (6)	C13—H13	0.9300
O4—C8	1.25 (4)	C14—C15	1.348 (8)
O4'—C8	1.08 (3)	C14—H14	0.9300
O5—C18	1.304 (5)	C15—C16	1.367 (7)
O5—C27	1.488 (18)	C15—H15	0.9300
O5—C27'	1.59 (5)	C16—H16	0.9300
O6—C18	1.186 (4)	C17—H17A	0.9600
N1—C2	1.333 (4)	C17—H17B	0.9600
N1—C6	1.330 (4)	C17—H17C	0.9600
N2—C1	1.325 (4)	C18—C19	1.498 (5)
N2—C9	1.441 (4)	C19—C20	1.514 (5)
N2—H2	0.8600	C19—H19	0.9800
N3—C7	1.327 (5)	C20—C21	1.485 (5)
N3—C19	1.445 (4)	C20—H20A	0.9700
N3—H3	0.8600	C20—H20B	0.9700
C1—C2	1.493 (5)	C21—C26	1.357 (6)
C2—C3	1.373 (5)	C21—C22	1.377 (6)
C3—C4	1.371 (5)	C22—C23	1.367 (6)
C3—H3A	0.9300	C22—H22	0.9300
C4—C5	1.374 (5)	C23—C24	1.343 (7)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.384 (5)	C24—C25	1.349 (7)
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.492 (5)	C25—C26	1.384 (6)
C8—C9	1.501 (6)	C25—H25	0.9300
C9—C10	1.532 (5)	C26—H26	0.9300
C9—H9	0.9800	C27—H27A	0.9600
C10—C11	1.499 (5)	C27—H27B	0.9600
C10—H10A	0.9700	C27—H27C	0.9600
C10—H10B	0.9700	C27'—H27D	0.9600
C11—C16	1.361 (5)	C27'—H27E	0.9600
C11—C12	1.368 (5)	C27'—H27F	0.9600

C8—O3—C17	117.7 (4)	C13—C14—C15	118.7 (5)
C18—O5—C27	116.0 (9)	C13—C14—H14	120.7
C18—O5—C27'	105 (2)	C15—C14—H14	120.7
C6—N1—C2	117.7 (3)	C14—C15—C16	120.9 (5)
C1—N2—C9	124.2 (3)	C14—C15—H15	119.5
C1—N2—H2	117.9	C16—C15—H15	119.5
C9—N2—H2	117.9	C11—C16—C15	121.1 (5)
C7—N3—C19	120.5 (3)	C11—C16—H16	119.5
C7—N3—H3	119.7	C15—C16—H16	119.5
C19—N3—H3	119.7	O3—C17—H17A	109.5
O1—C1—N2	123.9 (3)	O3—C17—H17B	109.5
O1—C1—C2	121.1 (3)	H17A—C17—H17B	109.5
N2—C1—C2	115.0 (3)	O3—C17—H17C	109.5
N1—C2—C3	122.9 (3)	H17A—C17—H17C	109.5
N1—C2—C1	116.1 (3)	H17B—C17—H17C	109.5
C3—C2—C1	120.9 (3)	O6—C18—O5	123.5 (4)
C4—C3—C2	118.9 (3)	O6—C18—C19	126.0 (4)
C4—C3—H3A	120.5	O5—C18—C19	110.4 (3)
C2—C3—H3A	120.5	N3—C19—C18	111.1 (3)
C3—C4—C5	119.1 (4)	N3—C19—C20	110.5 (3)
C3—C4—H4	120.5	C18—C19—C20	111.9 (3)
C5—C4—H4	120.5	N3—C19—H19	107.7
C4—C5—C6	118.3 (4)	C18—C19—H19	107.7
C4—C5—H5	120.8	C20—C19—H19	107.7
C6—C5—H5	120.8	C21—C20—C19	113.6 (3)
N1—C6—C5	123.0 (3)	C21—C20—H20A	108.8
N1—C6—C7	117.1 (3)	C19—C20—H20A	108.8
C5—C6—C7	119.8 (3)	C21—C20—H20B	108.8
O2—C7—N3	123.2 (3)	C19—C20—H20B	108.8
O2—C7—C6	121.2 (3)	H20A—C20—H20B	107.7
N3—C7—C6	115.6 (3)	C26—C21—C22	116.8 (4)
O4'—C8—O3	118 (3)	C26—C21—C20	121.4 (4)
O4—C8—O3	121.1 (7)	C22—C21—C20	121.7 (4)
O4'—C8—C9	121 (3)	C23—C22—C21	122.0 (4)
O4—C8—C9	123.9 (7)	C23—C22—H22	119.0
O3—C8—C9	113.3 (4)	C21—C22—H22	119.0
N2—C9—C8	109.5 (3)	C24—C23—C22	119.9 (5)
N2—C9—C10	111.0 (3)	C24—C23—H23	120.0
C8—C9—C10	111.2 (3)	C22—C23—H23	120.0
N2—C9—H9	108.4	C23—C24—C25	119.7 (4)
C8—C9—H9	108.4	C23—C24—H24	120.1
C10—C9—H9	108.4	C25—C24—H24	120.1
C11—C10—C9	113.8 (3)	C24—C25—C26	120.4 (4)
C11—C10—H10A	108.8	C24—C25—H25	119.8
C9—C10—H10A	108.8	C26—C25—H25	119.8
C11—C10—H10B	108.8	C21—C26—C25	121.1 (4)
C9—C10—H10B	108.8	C21—C26—H26	119.4
H10A—C10—H10B	107.7	C25—C26—H26	119.4
C16—C11—C12	117.5 (4)	O5—C27—H27A	109.5
C16—C11—C10	121.8 (4)	O5—C27—H27B	109.5
C12—C11—C10	120.7 (4)	O5—C27—H27C	109.5
C11—C12—C13	120.7 (5)	O5—C27'—H27D	109.5
C11—C12—H12	119.7	O5—C27'—H27E	109.5
C13—C12—H12	119.7	H27D—C27'—H27E	111.0
C14—C13—C12	121.2 (5)	O5—C27'—H27F	109.5
C14—C13—H13	119.4	H27D—C27'—H27F	109.5
C12—C13—H13	119.4	H27E—C27'—H27F	109.5

C9—N2—C1—O1	1.6 (5)	C8—C9—C10—C11	172.0 (3)
C9—N2—C1—C2	−175.8 (3)	C9—C10—C11—C16	79.1 (5)
C6—N1—C2—C3	−3.4 (5)	C9—C10—C11—C12	−100.7 (4)
C6—N1—C2—C1	173.9 (3)	C16—C11—C12—C13	0.4 (6)
O1—C1—C2—N1	−159.1 (3)	C10—C11—C12—C13	−179.8 (4)
N2—C1—C2—N1	18.4 (4)	C11—C12—C13—C14	−0.7 (8)
O1—C1—C2—C3	18.2 (5)	C12—C13—C14—C15	0.5 (8)
N2—C1—C2—C3	−164.3 (3)	C13—C14—C15—C16	0.1 (8)
N1—C2—C3—C4	3.0 (5)	C12—C11—C16—C15	0.2 (7)
C1—C2—C3—C4	−174.1 (3)	C10—C11—C16—C15	−179.7 (4)
C2—C3—C4—C5	−0.6 (6)	C14—C15—C16—C11	−0.4 (8)
C3—C4—C5—C6	−1.3 (6)	C27—O5—C18—O6	9 (3)
C2—N1—C6—C5	1.3 (5)	C27'—O5—C18—O6	−27 (4)
C2—N1—C6—C7	−175.5 (3)	C27—O5—C18—C19	−167 (2)
C4—C5—C6—N1	1.0 (6)	C27'—O5—C18—C19	157 (4)
C4—C5—C6—C7	177.7 (3)	C7—N3—C19—C18	−60.0 (4)
C19—N3—C7—O2	−8.3 (6)	C7—N3—C19—C20	175.2 (3)
C19—N3—C7—C6	169.9 (3)	O6—C18—C19—N3	134.5 (5)
N1—C6—C7—O2	174.0 (3)	O5—C18—C19—N3	−49.4 (5)
C5—C6—C7—O2	−3.0 (6)	O6—C18—C19—C20	−101.5 (5)
N1—C6—C7—N3	−4.3 (5)	O5—C18—C19—C20	74.6 (5)
C5—C6—C7—N3	178.8 (3)	N3—C19—C20—C21	175.3 (3)
C17—O3—C8—O4'	−33 (9)	C18—C19—C20—C21	50.9 (5)
C17—O3—C8—O4	12 (3)	C19—C20—C21—C26	76.9 (5)
C17—O3—C8—C9	177.0 (4)	C19—C20—C21—C22	−101.0 (5)
C1—N2—C9—C8	−102.6 (4)	C26—C21—C22—C23	0.0 (7)
C1—N2—C9—C10	134.3 (3)	C20—C21—C22—C23	178.0 (4)
O4'—C8—C9—N2	24 (9)	C21—C22—C23—C24	0.6 (8)
O4—C8—C9—N2	−23 (3)	C22—C23—C24—C25	−1.2 (7)
O3—C8—C9—N2	172.4 (3)	C23—C24—C25—C26	1.2 (8)
O4'—C8—C9—C10	147 (9)	C22—C21—C26—C25	0.0 (6)
O4—C8—C9—C10	100 (3)	C20—C21—C26—C25	−178.0 (4)
O3—C8—C9—C10	−64.7 (5)	C24—C25—C26—C21	−0.6 (7)
N2—C9—C10—C11	−65.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.86	2.37	3.178 (4)	157
N3—H3···O1ⁱ	0.86	2.40	3.190 (4)	154

Symmetry code: (i) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₇N₃O₆
M_r	489.52
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	9.1549 (11), 9.9319 (12), 27.83 (2)
V (Å³)	2530 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.986, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	12674, 2650, 1929
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.134, 1.05
No. of reflections	2650
No. of parameters	349
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.86	2.37	3.178 (4)	157.3
N3—H3···O1ⁱ	0.86	2.40	3.190 (4)	153.6

Symmetry code: (i) x+1/2, −y+1/2, −z.

Acknowledgements

The authors thank the Key Subject Research Foundation of Shandong Province (grant No. XTD0704) and Shandong Province Education Department (grant No. J07YC10) for support of this work.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Amr, A. E., Abd El-Salam, O. I., Attia, A. E. & Stibor, I. (1999). Collect. Czech. Chem. Commun. 64, 288–298. Web of Science CrossRef CAS Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Darshan, R., Haridas, V., Gilardi, R. & Isabella, L. K. (1998). J. Am. Chem. Soc. 120, 10793–10800. Google Scholar
Moriuchi, T., Shen, X. & Hirao, T. (2006). Tetrahedron, 62, 12237–12246. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 7| July 2009| Page o1713

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(−)-Di­methyl 3,3′-di­phenyl-2,2′-[pyridine-2,6-diylbis(carbonyl­imino)]di­propanoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

(−)-Dimethyl 3,3′-diphenyl-2,2′-[pyridine-2,6-diylbis(carbonylimino)]dipropanoate