Diethyl 4-meth­oxyoxalyl-3,5-diphenyl­pyrrolidine-2,2-dicarboxyl­ate

He, Y.-Q.; Chen, J.-Q.

doi:10.1107/S160053681201392X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1325

doi:10.1107/S160053681201392X

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Diethyl 4-methoxyoxalyl-3,5-diphenylpyrrolidine-2,2-dicarboxylate

Yan-Qin He ^a ^* and Jin-Quan Chen ^a

^aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: heyanqin123@yahoo.com.cn

(Received 28 March 2012; accepted 30 March 2012; online 6 April 2012)

In the title compound, C₂₅H₂₇NO₇, the pyrrolidine ring exhibits an envelope conformation and the benzene rings form a dihedral angle of 33.47 (11)°. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. Weak C—H⋯O interactions link the dimers into layers parallel to the bc plane.

Related literature

For applications of pyrrolidine derivatives, see: Shih et al. (1995 ); Enyedy et al. (2001 ); Kravchenko et al. (2005 ); Lack et al. (2011 ).

Experimental

Crystal data

C₂₅H₂₇NO₇
M_r = 453.48
Monoclinic, P 2₁ /c
a = 8.8779 (3) Å
b = 20.3438 (6) Å
c = 13.5740 (5) Å
β = 102.213 (3)°
V = 2396.12 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 290 K
0.38 × 0.35 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.966, T_max = 0.973
14990 measured reflections
4887 independent reflections
3129 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.133
S = 1.02
4887 reflections
305 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.88 (2)	2.27 (2)	3.061 (2)	150 (2)
C23—H23⋯O3ⁱⁱ	0.93	2.54	3.461 (3)	170
C25—H25⋯O7ⁱⁱⁱ	0.93	2.60	3.526 (3)	172
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+2, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201392X/cv5272sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201392X/cv5272Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201392X/cv5272Isup3.cml

checkCIF report

Comment top

Pyrrolidine derivatives have been found to be the core of numerous natural products and pharmaceutical candidates, see: Shih et al. (1995); Enyedy et al. (2001); Kravchenko et al. (2005); Lack et al. (2011). Herein, we report the crystal structure of the title compound (I).

The bond lengths and angles in (I) are normal. The pyrrolidine ring exhibits an envelope conformation, with the C2 atom occupying the flap position (Fig. 1). Two benzene rings - C12—C17 and C21—C26, respectively - form a dihedral angle of 33.47 (11)°. In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers, and weak C—H···O interactions (Table 1) link further these dimers into layers parallel to bc plane.

Related literature top

For applications of pyrrolidine derivatives, see: Shih et al. (1995); Enyedy et al. (2001); Kravchenko et al. (2005); Lack et al. (2011).

Experimental top

To a flame-dried test tube was added N,N-dimethyl-1-[2-(diphenylphosphino) ferrocenyl]ethylamine (0.04 mmol), copper(II) trifluoromethanesulfonate (0.04 mmol), THF (O.5 ml), benzaldehyde (0.24 mmol) and diethyl A-aminomalonate (0.24 mmol) under an argon atmosphere. After the mixture was stirred at room temperature for 2 h, a solution of 2-Oxo-4-phenyl-but-3-enoic acid methyl ester (0.2 mmol) in THF (1.0 ml) was added through a syringe in one portion and the resulting mixture was stirred at room temperature until TLC showed no starting material left. Then, solvent was removed and the residue was purified directly by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 20/1 to 5/1) to yield product. The colourless single crystals suitable for X-ray diffraction were obtained in methanol solvent by slow evaporation.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids and the atomic numbering.

Diethyl 4-methoxyoxalyl-3,5-diphenylpyrrolidine-2,2-dicarboxylate top

Crystal data top

C₂₅H₂₇NO₇	F(000) = 960
M_r = 453.48	D_x = 1.257 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4380 reflections
a = 8.8779 (3) Å	θ = 3.2–29.1°
b = 20.3438 (6) Å	µ = 0.09 mm⁻¹
c = 13.5740 (5) Å	T = 290 K
β = 102.213 (3)°	Block, colorless
V = 2396.12 (14) Å³	0.38 × 0.35 × 0.30 mm
Z = 4

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	4887 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3129 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 15.9149 pixels mm^-1	θ_max = 26.4°, θ_min = 3.2°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −25→25
T_min = 0.966, T_max = 0.973	l = −16→14
14990 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0554P)² + 0.3662P] where P = (F_o² + 2F_c²)/3
4887 reflections	(Δ/σ)_max < 0.001
305 parameters	Δρ_max = 0.28 e Å⁻³
8 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₅H₂₇NO₇	V = 2396.12 (14) Å³
M_r = 453.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8779 (3) Å	µ = 0.09 mm⁻¹
b = 20.3438 (6) Å	T = 290 K
c = 13.5740 (5) Å	0.38 × 0.35 × 0.30 mm
β = 102.213 (3)°

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	4887 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	3129 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.973	R_int = 0.033
14990 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	8 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.28 e Å⁻³
4887 reflections	Δρ_min = −0.26 e Å⁻³
305 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	0.9482 (2)	0.04749 (8)	0.86894 (15)	0.0445 (4)
O1	0.75874 (18)	0.01366 (7)	1.00477 (12)	0.0587 (4)
O2	0.68505 (17)	0.11814 (7)	1.01209 (11)	0.0537 (4)
O3	0.90888 (18)	0.20277 (8)	0.85551 (13)	0.0627 (5)
O4	0.99367 (18)	0.16006 (7)	1.00924 (12)	0.0606 (5)
O5	0.6663 (2)	0.05129 (8)	0.58463 (13)	0.0646 (5)
O6	0.5961 (2)	−0.10174 (9)	0.66768 (15)	0.0833 (6)
O7	0.6680 (2)	−0.07505 (8)	0.52526 (13)	0.0672 (5)
C2	0.8329 (2)	0.09267 (9)	0.89093 (15)	0.0390 (5)
C3	0.7135 (2)	0.09231 (9)	0.78941 (15)	0.0393 (5)
H3	0.7590	0.1168	0.7408	0.047*
C4	0.7112 (2)	0.01965 (9)	0.75916 (16)	0.0416 (5)
H4	0.6324	−0.0027	0.7877	0.050*
C5	0.8726 (2)	−0.00897 (10)	0.81100 (16)	0.0427 (5)
H5	0.8575	−0.0436	0.8582	0.051*
C6	0.7574 (2)	0.06980 (10)	0.97687 (16)	0.0418 (5)
C7	0.5949 (3)	0.10022 (14)	1.0861 (2)	0.0740 (8)
H7A	0.5254	0.0644	1.0608	0.089*
H7B	0.6625	0.0862	1.1483	0.089*
C8	0.5078 (5)	0.15783 (19)	1.1041 (3)	0.1267 (13)
H8A	0.4510	0.1746	1.0409	0.190*
H8B	0.5773	0.1910	1.1372	0.190*
H8C	0.4374	0.1460	1.1460	0.190*
C9	0.9123 (2)	0.15908 (11)	0.91495 (18)	0.0453 (5)
C10	1.0665 (3)	0.22220 (14)	1.0448 (2)	0.0809 (9)
H10A	1.1018	0.2439	0.9902	0.097*
H10B	1.1555	0.2140	1.0986	0.097*
C11	0.9557 (4)	0.26554 (15)	1.0823 (3)	0.1000 (11)
H11A	0.8684	0.2741	1.0287	0.150*
H11B	1.0053	0.3063	1.1056	0.150*
H11C	0.9219	0.2442	1.1369	0.150*
C12	0.5595 (2)	0.12441 (10)	0.79130 (15)	0.0412 (5)
C13	0.4339 (2)	0.09043 (12)	0.81017 (19)	0.0570 (6)
H13	0.4396	0.0450	0.8180	0.068*
C14	0.3000 (3)	0.12289 (14)	0.8176 (2)	0.0704 (7)
H14	0.2169	0.0991	0.8307	0.084*
C15	0.2887 (3)	0.18935 (14)	0.8060 (2)	0.0683 (7)
H15	0.1988	0.2110	0.8118	0.082*
C16	0.4104 (3)	0.22371 (13)	0.7859 (2)	0.0671 (7)
H16	0.4033	0.2691	0.7776	0.080*
C17	0.5440 (3)	0.19164 (10)	0.77789 (18)	0.0545 (6)
H17	0.6255	0.2157	0.7631	0.065*
C18	0.6739 (2)	0.00889 (10)	0.64679 (17)	0.0459 (5)
C19	0.6410 (3)	−0.06290 (12)	0.61527 (19)	0.0533 (6)
C20	0.6394 (4)	−0.14192 (14)	0.4894 (2)	0.0933 (10)
H20A	0.6611	−0.1457	0.4232	0.140*
H20B	0.5335	−0.1530	0.4866	0.140*
H20C	0.7048	−0.1714	0.5345	0.140*
C21	0.9705 (2)	−0.03601 (10)	0.74167 (17)	0.0466 (5)
C22	0.9944 (3)	−0.10277 (12)	0.7365 (2)	0.0651 (7)
H22	0.9494	−0.1311	0.7757	0.078*
C23	1.0847 (4)	−0.12831 (15)	0.6737 (2)	0.0820 (9)
H23	1.0998	−0.1734	0.6709	0.098*
C24	1.1512 (4)	−0.08695 (18)	0.6163 (2)	0.0861 (9)
H24	1.2127	−0.1040	0.5748	0.103*
C25	1.1283 (3)	−0.02117 (16)	0.6190 (2)	0.0783 (8)
H25	1.1730	0.0067	0.5790	0.094*
C26	1.0380 (3)	0.00470 (12)	0.68185 (19)	0.0611 (6)
H26	1.0228	0.0499	0.6836	0.073*
H1N	1.016 (2)	0.0357 (10)	0.9232 (14)	0.054 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0426 (10)	0.0438 (10)	0.0464 (12)	0.0056 (8)	0.0077 (9)	−0.0022 (9)
O1	0.0719 (11)	0.0459 (9)	0.0627 (11)	0.0056 (7)	0.0240 (8)	0.0149 (8)
O2	0.0648 (10)	0.0496 (9)	0.0533 (10)	0.0054 (7)	0.0277 (8)	0.0016 (7)
O3	0.0745 (11)	0.0482 (9)	0.0640 (11)	−0.0176 (8)	0.0113 (9)	0.0053 (9)
O4	0.0645 (10)	0.0603 (10)	0.0520 (10)	−0.0165 (8)	0.0009 (8)	−0.0057 (8)
O5	0.0861 (12)	0.0569 (10)	0.0495 (10)	0.0043 (8)	0.0110 (9)	0.0064 (8)
O6	0.1233 (17)	0.0567 (11)	0.0763 (14)	−0.0250 (10)	0.0357 (12)	−0.0118 (10)
O7	0.0863 (12)	0.0633 (11)	0.0497 (11)	0.0081 (9)	0.0093 (9)	−0.0136 (9)
C2	0.0406 (11)	0.0356 (10)	0.0417 (12)	−0.0003 (8)	0.0104 (9)	0.0006 (9)
C3	0.0429 (11)	0.0374 (11)	0.0384 (12)	−0.0001 (8)	0.0106 (9)	0.0025 (9)
C4	0.0456 (12)	0.0371 (11)	0.0438 (13)	−0.0015 (8)	0.0131 (9)	0.0003 (9)
C5	0.0505 (12)	0.0372 (11)	0.0418 (12)	0.0025 (9)	0.0131 (10)	0.0036 (9)
C6	0.0425 (11)	0.0418 (12)	0.0402 (12)	0.0015 (9)	0.0066 (9)	0.0012 (10)
C7	0.0804 (18)	0.0894 (19)	0.0637 (18)	0.0056 (14)	0.0409 (15)	0.0081 (15)
C8	0.142 (2)	0.132 (2)	0.129 (2)	0.0343 (16)	0.0808 (17)	−0.0039 (16)
C9	0.0423 (12)	0.0439 (12)	0.0519 (15)	−0.0020 (9)	0.0152 (10)	−0.0022 (11)
C10	0.087 (2)	0.0787 (19)	0.072 (2)	−0.0357 (16)	0.0045 (16)	−0.0169 (16)
C11	0.141 (3)	0.072 (2)	0.085 (2)	−0.012 (2)	0.019 (2)	−0.0180 (18)
C12	0.0449 (12)	0.0424 (11)	0.0368 (12)	0.0007 (9)	0.0094 (9)	0.0013 (9)
C13	0.0479 (13)	0.0519 (13)	0.0731 (18)	−0.0032 (10)	0.0171 (12)	−0.0031 (12)
C14	0.0472 (14)	0.0823 (19)	0.085 (2)	−0.0060 (13)	0.0218 (13)	−0.0096 (16)
C15	0.0543 (15)	0.085 (2)	0.0671 (18)	0.0218 (13)	0.0154 (13)	−0.0022 (15)
C16	0.0718 (17)	0.0548 (15)	0.0766 (19)	0.0199 (13)	0.0201 (14)	0.0073 (13)
C17	0.0546 (14)	0.0469 (13)	0.0642 (16)	0.0049 (10)	0.0171 (12)	0.0077 (11)
C18	0.0439 (12)	0.0464 (12)	0.0471 (13)	0.0020 (9)	0.0087 (10)	−0.0010 (11)
C19	0.0553 (14)	0.0530 (14)	0.0491 (15)	0.0012 (11)	0.0056 (11)	−0.0052 (12)
C20	0.131 (3)	0.0688 (18)	0.072 (2)	0.0200 (17)	0.0035 (19)	−0.0275 (16)
C21	0.0476 (12)	0.0470 (13)	0.0442 (13)	0.0067 (9)	0.0072 (10)	−0.0009 (10)
C22	0.0812 (18)	0.0505 (14)	0.0649 (17)	0.0158 (12)	0.0183 (14)	−0.0015 (12)
C23	0.102 (2)	0.0648 (18)	0.080 (2)	0.0265 (16)	0.0218 (18)	−0.0160 (16)
C24	0.083 (2)	0.103 (2)	0.077 (2)	0.0192 (18)	0.0290 (17)	−0.025 (2)
C25	0.0768 (19)	0.100 (2)	0.0669 (19)	−0.0079 (16)	0.0358 (15)	−0.0105 (17)
C26	0.0670 (16)	0.0576 (15)	0.0631 (17)	−0.0018 (12)	0.0236 (13)	−0.0036 (13)

Geometric parameters (Å, º) top

N1—C2	1.453 (2)	C10—H10A	0.9700
N1—C5	1.472 (3)	C10—H10B	0.9700
N1—H1N	0.878 (16)	C11—H11A	0.9600
O1—C6	1.203 (2)	C11—H11B	0.9600
O2—C6	1.318 (2)	C11—H11C	0.9600
O2—C7	1.457 (3)	C12—C13	1.381 (3)
O3—C9	1.196 (3)	C12—C17	1.383 (3)
O4—C9	1.330 (3)	C13—C14	1.382 (3)
O4—C10	1.455 (3)	C13—H13	0.9300
O5—C18	1.198 (3)	C14—C15	1.362 (4)
O6—C19	1.187 (3)	C14—H14	0.9300
O7—C19	1.317 (3)	C15—C16	1.362 (4)
O7—C20	1.449 (3)	C15—H15	0.9300
C2—C9	1.527 (3)	C16—C17	1.378 (3)
C2—C6	1.536 (3)	C16—H16	0.9300
C2—C3	1.551 (3)	C17—H17	0.9300
C3—C12	1.520 (3)	C18—C19	1.533 (3)
C3—C4	1.533 (3)	C20—H20A	0.9600
C3—H3	0.9800	C20—H20B	0.9600
C4—C18	1.507 (3)	C20—H20C	0.9600
C4—C5	1.569 (3)	C21—C22	1.379 (3)
C4—H4	0.9800	C21—C26	1.382 (3)
C5—C21	1.513 (3)	C22—C23	1.388 (4)
C5—H5	0.9800	C22—H22	0.9300
C7—C8	1.453 (4)	C23—C24	1.364 (4)
C7—H7A	0.9700	C23—H23	0.9300
C7—H7B	0.9700	C24—C25	1.355 (4)
C8—H8A	0.9600	C24—H24	0.9300
C8—H8B	0.9600	C25—C26	1.392 (4)
C8—H8C	0.9600	C25—H25	0.9300
C10—C11	1.489 (4)	C26—H26	0.9300

C2—N1—C5	110.00 (16)	C10—C11—H11A	109.5
C2—N1—H1N	112.7 (15)	C10—C11—H11B	109.5
C5—N1—H1N	112.8 (14)	H11A—C11—H11B	109.5
C6—O2—C7	116.37 (18)	C10—C11—H11C	109.5
C9—O4—C10	116.42 (19)	H11A—C11—H11C	109.5
C19—O7—C20	115.8 (2)	H11B—C11—H11C	109.5
N1—C2—C9	106.88 (16)	C13—C12—C17	117.3 (2)
N1—C2—C6	113.85 (16)	C13—C12—C3	123.52 (18)
C9—C2—C6	111.21 (17)	C17—C12—C3	119.14 (18)
N1—C2—C3	101.17 (16)	C12—C13—C14	121.0 (2)
C9—C2—C3	113.06 (16)	C12—C13—H13	119.5
C6—C2—C3	110.31 (15)	C14—C13—H13	119.5
C12—C3—C4	117.24 (16)	C15—C14—C13	120.6 (2)
C12—C3—C2	115.56 (17)	C15—C14—H14	119.7
C4—C3—C2	102.13 (15)	C13—C14—H14	119.7
C12—C3—H3	107.1	C16—C15—C14	119.4 (2)
C4—C3—H3	107.1	C16—C15—H15	120.3
C2—C3—H3	107.1	C14—C15—H15	120.3
C18—C4—C3	113.50 (17)	C15—C16—C17	120.4 (2)
C18—C4—C5	112.60 (17)	C15—C16—H16	119.8
C3—C4—C5	106.19 (15)	C17—C16—H16	119.8
C18—C4—H4	108.1	C16—C17—C12	121.4 (2)
C3—C4—H4	108.1	C16—C17—H17	119.3
C5—C4—H4	108.1	C12—C17—H17	119.3
N1—C5—C21	111.04 (17)	O5—C18—C4	125.16 (19)
N1—C5—C4	102.72 (15)	O5—C18—C19	120.7 (2)
C21—C5—C4	116.51 (17)	C4—C18—C19	114.14 (19)
N1—C5—H5	108.8	O6—C19—O7	125.5 (2)
C21—C5—H5	108.8	O6—C19—C18	122.4 (2)
C4—C5—H5	108.8	O7—C19—C18	112.1 (2)
O1—C6—O2	124.6 (2)	O7—C20—H20A	109.5
O1—C6—C2	123.36 (19)	O7—C20—H20B	109.5
O2—C6—C2	111.96 (17)	H20A—C20—H20B	109.5
C8—C7—O2	107.7 (2)	O7—C20—H20C	109.5
C8—C7—H7A	110.2	H20A—C20—H20C	109.5
O2—C7—H7A	110.2	H20B—C20—H20C	109.5
C8—C7—H7B	110.2	C22—C21—C26	118.0 (2)
O2—C7—H7B	110.2	C22—C21—C5	120.3 (2)
H7A—C7—H7B	108.5	C26—C21—C5	121.66 (19)
C7—C8—H8A	109.5	C21—C22—C23	121.0 (3)
C7—C8—H8B	109.5	C21—C22—H22	119.5
H8A—C8—H8B	109.5	C23—C22—H22	119.5
C7—C8—H8C	109.5	C24—C23—C22	119.7 (3)
H8A—C8—H8C	109.5	C24—C23—H23	120.1
H8B—C8—H8C	109.5	C22—C23—H23	120.1
O3—C9—O4	124.67 (19)	C25—C24—C23	120.5 (3)
O3—C9—C2	124.7 (2)	C25—C24—H24	119.7
O4—C9—C2	110.54 (18)	C23—C24—H24	119.7
O4—C10—C11	110.4 (2)	C24—C25—C26	120.0 (3)
O4—C10—H10A	109.6	C24—C25—H25	120.0
C11—C10—H10A	109.6	C26—C25—H25	120.0
O4—C10—H10B	109.6	C21—C26—C25	120.7 (2)
C11—C10—H10B	109.6	C21—C26—H26	119.6
H10A—C10—H10B	108.1	C25—C26—H26	119.6

C5—N1—C2—C9	−159.71 (17)	C9—O4—C10—C11	84.5 (3)
C5—N1—C2—C6	77.1 (2)	C4—C3—C12—C13	28.5 (3)
C5—N1—C2—C3	−41.2 (2)	C2—C3—C12—C13	−92.0 (2)
N1—C2—C3—C12	168.35 (16)	C4—C3—C12—C17	−154.38 (19)
C9—C2—C3—C12	−77.7 (2)	C2—C3—C12—C17	85.1 (2)
C6—C2—C3—C12	47.5 (2)	C17—C12—C13—C14	−1.5 (4)
N1—C2—C3—C4	39.90 (18)	C3—C12—C13—C14	175.6 (2)
C9—C2—C3—C4	153.85 (16)	C12—C13—C14—C15	0.3 (4)
C6—C2—C3—C4	−80.93 (19)	C13—C14—C15—C16	0.6 (4)
C12—C3—C4—C18	82.3 (2)	C14—C15—C16—C17	−0.3 (4)
C2—C3—C4—C18	−150.29 (17)	C15—C16—C17—C12	−1.0 (4)
C12—C3—C4—C5	−153.43 (17)	C13—C12—C17—C16	1.9 (4)
C2—C3—C4—C5	−26.1 (2)	C3—C12—C17—C16	−175.4 (2)
C2—N1—C5—C21	149.70 (17)	C3—C4—C18—O5	9.5 (3)
C2—N1—C5—C4	24.5 (2)	C5—C4—C18—O5	−111.1 (2)
C18—C4—C5—N1	127.43 (18)	C3—C4—C18—C19	−169.00 (17)
C3—C4—C5—N1	2.6 (2)	C5—C4—C18—C19	70.3 (2)
C18—C4—C5—C21	5.8 (2)	C20—O7—C19—O6	−0.1 (4)
C3—C4—C5—C21	−118.94 (19)	C20—O7—C19—C18	−179.9 (2)
C7—O2—C6—O1	−3.3 (3)	O5—C18—C19—O6	−153.7 (2)
C7—O2—C6—C2	173.36 (18)	C4—C18—C19—O6	24.9 (3)
N1—C2—C6—O1	−19.7 (3)	O5—C18—C19—O7	26.1 (3)
C9—C2—C6—O1	−140.5 (2)	C4—C18—C19—O7	−155.34 (19)
C3—C2—C6—O1	93.2 (2)	N1—C5—C21—C22	133.7 (2)
N1—C2—C6—O2	163.56 (16)	C4—C5—C21—C22	−109.2 (2)
C9—C2—C6—O2	42.8 (2)	N1—C5—C21—C26	−46.4 (3)
C3—C2—C6—O2	−83.5 (2)	C4—C5—C21—C26	70.7 (3)
C6—O2—C7—C8	−171.9 (3)	C26—C21—C22—C23	0.5 (4)
C10—O4—C9—O3	8.3 (3)	C5—C21—C22—C23	−179.6 (2)
C10—O4—C9—C2	−175.66 (19)	C21—C22—C23—C24	0.1 (4)
N1—C2—C9—O3	96.2 (2)	C22—C23—C24—C25	−0.8 (5)
C6—C2—C9—O3	−139.0 (2)	C23—C24—C25—C26	0.8 (5)
C3—C2—C9—O3	−14.3 (3)	C22—C21—C26—C25	−0.5 (4)
N1—C2—C9—O4	−79.9 (2)	C5—C21—C26—C25	179.6 (2)
C6—C2—C9—O4	45.0 (2)	C24—C25—C26—C21	−0.1 (4)
C3—C2—C9—O4	169.70 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.88 (2)	2.27 (2)	3.061 (2)	150 (2)
C23—H23···O3ⁱⁱ	0.93	2.54	3.461 (3)	170
C25—H25···O7ⁱⁱⁱ	0.93	2.60	3.526 (3)	172

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₇NO₇
M_r	453.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	290
a, b, c (Å)	8.8779 (3), 20.3438 (6), 13.5740 (5)
β (°)	102.213 (3)
V (Å³)	2396.12 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.38 × 0.35 × 0.30

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.966, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	14990, 4887, 3129
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.133, 1.02
No. of reflections	4887
No. of parameters	305
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.26

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.878 (16)	2.269 (18)	3.061 (2)	150 (2)
C23—H23···O3ⁱⁱ	0.93	2.54	3.461 (3)	169.6
C25—H25···O7ⁱⁱⁱ	0.93	2.60	3.526 (3)	172.2

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+2, −y, −z+1.

Acknowledgements

The authors thank the Centre for Testing and Analysis, Cheng Du Branch Chinese Academy of Sciences, for analytic support.

References

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