2,2-Diethyl 3,4-dimethyl 5-(4-cyano­phen­yl)pyrrolidine-2,2,3,4-tetra­carboxyl­ate

He, L.

doi:10.1107/S1600536812029625

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2363

https://doi.org/10.1107/S1600536812029625

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2,2-Diethyl 3,4-dimethyl 5-(4-cyanophenyl)pyrrolidine-2,2,3,4-tetracarboxylate

Long He ^a ^*

^aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: helongcwnu@yahoo.com.cn

(Received 4 June 2012; accepted 28 June 2012; online 7 July 2012)

The title compound, C₂₁H₂₄N₂O₈, was synthesized by a 1,3-dipolar cycloaddition reaction of dimethyl fumarate, diethyl 2-aminomalonate and 4-cyanobenzaldehyde. Both methyl ester groups display a trans configuration and the pyrrolidine ring possesses an envelope conformation, with the C atom in the 3-position as the flap. In the crystal, N—H⋯N hydrogen bonds and weak C—H⋯O interactions occur.

Related literature

For the biological activity of pyrrolidine derivatives, see: Coldham & Hufton (2005 ); Pandey et al. (2006 ); Schreiber et al. (2000 ). For a related structure, see: He et al. (2010 ).

Experimental

Crystal data

C₂₁H₂₄N₂O₈
M_r = 432.42
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.4720 (2) Å
b = 10.3043 (2) Å
c = 25.8774 (5) Å
V = 2259.05 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.83 mm⁻¹
T = 291 K
0.38 × 0.30 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.744, T_max = 0.789
26556 measured reflections
2565 independent reflections
2050 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.141
S = 1.03
2565 reflections
288 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 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
N2—H1⋯N1ⁱ	0.86 (4)	2.47 (4)	3.240 (5)	148 (4)
C8—H8⋯O1ⁱⁱ	0.98	2.39	3.333 (4)	161 (1)
C13—H13C⋯O7ⁱⁱ	0.96	2.46	3.388 (6)	163
C18—H18C⋯O5ⁱⁱⁱ	0.96	2.55	3.453 (9)	157
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812029625/xu5557sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029625/xu5557Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029625/xu5557Isup3.cml

checkCIF report

Comment top

Facile synthesis of structurally diverse heterocycles is important in chemical biology. Five-membered pyrrolidines compounds is an important class of heterocyclic compounds with wide spread applications to the synthesis of biologically active compounds and natural alkaloids (Coldham & Hufton, 2005; Pandey et al., 2006; Schreiber et al., 2000). Its crystal structure is reported here.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The pyrrolidine ring possesses an envelope conformation. The crystal packing is stabilized by C—H···O and N—H···N hydrogen bonds (Table 1).

Related literature top

For the biological activity of pyrrolidine derivatives, see: Coldham & Hufton (2005); Pandey et al. (2006); Schreiber et al. (2000). For a related structure, see: He et al. (2010).

Experimental top

To a solution of 4-cyanobenzaldehyde (0.065 g, 0.5 mmol), sodium sulflate (0.1 g) and diethyl 2-aminomalonate (0.070 g, 0.4 mmol) in chloroform (4 ml) was added dimethyl fumarate (0.145 g, 1 mmol). The mixture was stirred at 323 K for 2 d and then cooled to room temperature, the solvent was evaporated under reduced pressure and the residues was purified by flash chromatograghy on silica gel. The colourless powder was obtained. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution.

Structure description top

For the biological activity of pyrrolidine derivatives, see: Coldham & Hufton (2005); Pandey et al. (2006); Schreiber et al. (2000). For a related structure, see: He et al. (2010).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

2,2-Diethyl 3,4-dimethyl 5-(4-cyanophenyl)pyrrolidine-2,2,3,4-tetracarboxylate top

Crystal data top

C₂₁H₂₄N₂O₈	D_x = 1.271 Mg m⁻³
M_r = 432.42	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 10771 reflections
a = 8.4720 (2) Å	θ = 1.7–72.3°
b = 10.3043 (2) Å	µ = 0.83 mm⁻¹
c = 25.8774 (5) Å	T = 291 K
V = 2259.05 (8) Å³	Block, colorless
Z = 4	0.38 × 0.30 × 0.30 mm
F(000) = 912

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2565 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2050 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 15.9149 pixels mm^-1	θ_max = 72.6°, θ_min = 3.4°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −12→10
T_min = 0.744, T_max = 0.789	l = −31→31
26556 measured reflections

Refinement top

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0724P)² + 0.5988P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2565 reflections	Δρ_max = 0.40 e Å⁻³
288 parameters	Δρ_min = −0.22 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (4)

Crystal data top

C₂₁H₂₄N₂O₈	V = 2259.05 (8) Å³
M_r = 432.42	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 8.4720 (2) Å	µ = 0.83 mm⁻¹
b = 10.3043 (2) Å	T = 291 K
c = 25.8774 (5) Å	0.38 × 0.30 × 0.30 mm

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2565 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	2050 reflections with I > 2σ(I)
T_min = 0.744, T_max = 0.789	R_int = 0.027
26556 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	2 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.40 e Å⁻³
2565 reflections	Δρ_min = −0.22 e Å⁻³
288 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
O2	1.0668 (3)	0.9425 (2)	0.20700 (8)	0.0707 (7)
O5	1.0369 (4)	0.7873 (2)	0.40309 (11)	0.0880 (9)
O8	0.8498 (4)	1.0544 (3)	0.46182 (9)	0.0865 (9)
N2	0.8356 (4)	0.9769 (3)	0.35733 (10)	0.0622 (7)
O1	1.1491 (5)	1.1320 (3)	0.23785 (10)	0.0928 (10)
C9	1.0464 (4)	0.9727 (3)	0.29624 (11)	0.0548 (7)
H9	1.1073	0.8930	0.3016	0.066*
O6	1.1628 (4)	0.9441 (3)	0.44645 (10)	0.0898 (9)
O4	1.3158 (4)	1.1691 (3)	0.37339 (11)	0.0874 (8)
O7	0.9598 (5)	1.2258 (3)	0.42249 (12)	0.1046 (12)
C5	0.7612 (4)	1.0072 (3)	0.26561 (11)	0.0542 (7)
C2	0.5727 (4)	1.1296 (3)	0.19214 (13)	0.0632 (9)
C8	0.8696 (4)	0.9382 (3)	0.30325 (11)	0.0530 (7)
H8	0.8559	0.8442	0.2997	0.064*
C12	1.0926 (4)	1.0266 (3)	0.24488 (12)	0.0597 (8)
C6	0.7360 (4)	1.1396 (3)	0.26702 (13)	0.0620 (8)
H6	0.7825	1.1885	0.2931	0.074*
C10	1.0857 (4)	1.0649 (3)	0.34090 (12)	0.0592 (8)
H10	1.0539	1.1535	0.3320	0.071*
C4	0.6885 (5)	0.9354 (4)	0.22681 (13)	0.0668 (9)
H4	0.7047	0.8462	0.2251	0.080*
C11	0.9802 (4)	1.0124 (3)	0.38427 (12)	0.0602 (8)
C7	0.6433 (4)	1.2009 (3)	0.23057 (14)	0.0658 (9)
H7	0.6287	1.2903	0.2320	0.079*
C19	0.9328 (5)	1.1127 (3)	0.42459 (13)	0.0716 (10)
C16	1.0612 (5)	0.8987 (3)	0.41186 (13)	0.0683 (10)
C3	0.5921 (5)	0.9951 (4)	0.19062 (15)	0.0754 (11)
H3	0.5409	0.9460	0.1656	0.091*
C14	1.2688 (5)	1.0600 (4)	0.35092 (14)	0.0719 (10)
C13	1.0929 (7)	0.9876 (5)	0.15484 (13)	0.0955 (15)
H13A	1.2035	1.0033	0.1497	0.115*
H13B	1.0352	1.0665	0.1493	0.115*
H13C	1.0575	0.9228	0.1308	0.115*
C20	0.7915 (8)	1.1323 (5)	0.50465 (15)	0.1021 (16)
H20A	0.8668	1.2001	0.5128	0.122*
H20B	0.6923	1.1729	0.4952	0.122*
C17	1.2540 (8)	0.8528 (5)	0.47718 (19)	0.1127 (19)
H17A	1.1848	0.7871	0.4916	0.135*
H17B	1.3318	0.8100	0.4556	0.135*
C15	1.4850 (5)	1.1640 (7)	0.3860 (2)	0.1114 (17)
H15A	1.5435	1.1382	0.3559	0.167*
H15B	1.5020	1.1022	0.4132	0.167*
H15C	1.5198	1.2481	0.3971	0.167*
C21	0.7690 (9)	1.0492 (6)	0.54894 (18)	0.121 (2)
H21A	0.8670	1.0078	0.5575	0.145*
H21B	0.6912	0.9845	0.5410	0.145*
H21C	0.7337	1.1003	0.5778	0.145*
C18	1.3299 (11)	0.9207 (8)	0.5172 (3)	0.189 (4)
H18A	1.2602	0.9860	0.5306	0.227*
H18B	1.4238	0.9610	0.5040	0.227*
H18C	1.3575	0.8613	0.5443	0.227*
O3	1.3504 (4)	0.9759 (4)	0.33931 (18)	0.1249 (14)
N1	0.4052 (5)	1.2386 (4)	0.12122 (16)	0.0982 (12)
C1	0.4786 (5)	1.1909 (4)	0.15304 (15)	0.0752 (10)
H1	0.780 (5)	0.924 (4)	0.3757 (16)	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.1013 (19)	0.0581 (13)	0.0527 (11)	−0.0096 (14)	0.0014 (12)	−0.0020 (11)
O5	0.126 (2)	0.0517 (14)	0.0863 (18)	0.0007 (16)	−0.0135 (18)	0.0065 (12)
O8	0.134 (3)	0.0700 (15)	0.0558 (12)	−0.0049 (18)	0.0108 (16)	−0.0103 (12)
N2	0.0743 (17)	0.0655 (17)	0.0469 (13)	−0.0087 (16)	−0.0029 (13)	0.0032 (12)
O1	0.148 (3)	0.0629 (16)	0.0677 (15)	−0.0344 (19)	0.0105 (18)	0.0011 (13)
C9	0.0710 (19)	0.0417 (15)	0.0516 (15)	0.0009 (15)	−0.0052 (15)	0.0015 (13)
O6	0.121 (2)	0.0700 (15)	0.0782 (16)	−0.0008 (18)	−0.0441 (17)	0.0122 (13)
O4	0.0833 (17)	0.094 (2)	0.0853 (17)	−0.0168 (17)	−0.0061 (16)	−0.0093 (16)
O7	0.170 (4)	0.0548 (16)	0.089 (2)	−0.0019 (19)	0.017 (2)	−0.0071 (13)
C5	0.0664 (18)	0.0482 (16)	0.0479 (15)	−0.0017 (15)	−0.0027 (14)	−0.0003 (13)
C2	0.0652 (19)	0.064 (2)	0.0606 (18)	0.0040 (18)	−0.0029 (16)	0.0074 (16)
C8	0.0706 (19)	0.0414 (14)	0.0472 (14)	−0.0014 (15)	−0.0051 (13)	0.0015 (13)
C12	0.074 (2)	0.0487 (16)	0.0569 (17)	0.0013 (16)	−0.0020 (16)	0.0020 (14)
C6	0.077 (2)	0.0460 (17)	0.0625 (18)	−0.0003 (17)	−0.0093 (17)	−0.0035 (15)
C10	0.078 (2)	0.0439 (15)	0.0556 (16)	−0.0060 (16)	−0.0124 (15)	0.0046 (14)
C4	0.085 (2)	0.0502 (17)	0.0648 (18)	0.0030 (18)	−0.0177 (19)	−0.0071 (16)
C11	0.088 (2)	0.0463 (16)	0.0465 (14)	−0.0032 (17)	−0.0107 (16)	0.0025 (13)
C7	0.069 (2)	0.0536 (18)	0.075 (2)	0.0036 (17)	−0.0033 (19)	0.0058 (17)
C19	0.106 (3)	0.0555 (19)	0.0537 (18)	0.001 (2)	−0.013 (2)	0.0007 (15)
C16	0.096 (3)	0.0555 (19)	0.0534 (17)	−0.0025 (19)	−0.0080 (19)	0.0078 (15)
C3	0.090 (3)	0.069 (2)	0.068 (2)	0.001 (2)	−0.024 (2)	−0.0083 (18)
C14	0.087 (3)	0.065 (2)	0.065 (2)	−0.011 (2)	−0.0043 (19)	−0.0079 (19)
C13	0.143 (4)	0.092 (3)	0.0511 (18)	−0.016 (3)	0.009 (2)	−0.0015 (19)
C20	0.147 (5)	0.094 (3)	0.064 (2)	0.014 (3)	0.006 (3)	−0.020 (2)
C17	0.140 (5)	0.094 (3)	0.104 (3)	0.014 (4)	−0.046 (4)	0.027 (3)
C15	0.064 (2)	0.148 (5)	0.122 (4)	−0.008 (3)	−0.014 (3)	−0.017 (4)
C21	0.158 (5)	0.123 (4)	0.081 (3)	−0.002 (4)	0.032 (3)	−0.016 (3)
C18	0.220 (9)	0.184 (7)	0.164 (6)	0.007 (7)	−0.125 (7)	0.040 (6)
O3	0.095 (2)	0.101 (2)	0.179 (4)	0.024 (2)	−0.037 (3)	−0.040 (3)
N1	0.092 (2)	0.103 (3)	0.099 (3)	0.012 (2)	−0.028 (2)	0.020 (2)
C1	0.070 (2)	0.080 (2)	0.075 (2)	0.004 (2)	−0.008 (2)	0.008 (2)

Geometric parameters (Å, º) top

O2—C12	1.327 (4)	C10—C14	1.573 (6)
O2—C13	1.445 (4)	C10—H10	0.9800
O5—C16	1.188 (4)	C4—C3	1.386 (5)
O8—C19	1.335 (5)	C4—H4	0.9300
O8—C20	1.455 (5)	C11—C19	1.523 (5)
N2—C11	1.456 (5)	C11—C16	1.534 (5)
N2—C8	1.484 (4)	C7—H7	0.9300
N2—H1	0.86 (2)	C3—H3	0.9300
O1—C12	1.201 (4)	C14—O3	1.149 (5)
C9—C12	1.493 (4)	C13—H13A	0.9600
C9—C10	1.532 (4)	C13—H13B	0.9600
C9—C8	1.550 (5)	C13—H13C	0.9600
C9—H9	0.9800	C20—C21	1.443 (7)
O6—C16	1.327 (5)	C20—H20A	0.9700
O6—C17	1.454 (5)	C20—H20B	0.9700
O4—C14	1.327 (5)	C17—C18	1.405 (8)
O4—C15	1.471 (5)	C17—H17A	0.9700
O7—C19	1.189 (5)	C17—H17B	0.9700
C5—C6	1.381 (4)	C15—H15A	0.9600
C5—C4	1.391 (5)	C15—H15B	0.9600
C5—C8	1.516 (4)	C15—H15C	0.9600
C2—C7	1.374 (5)	C21—H21A	0.9600
C2—C3	1.396 (5)	C21—H21B	0.9600
C2—C1	1.435 (5)	C21—H21C	0.9600
C8—H8	0.9800	C18—H18A	0.9600
C6—C7	1.380 (5)	C18—H18B	0.9600
C6—H6	0.9300	C18—H18C	0.9600
C10—C11	1.534 (5)	N1—C1	1.143 (5)

C12—O2—C13	117.1 (3)	O7—C19—O8	125.1 (4)
C19—O8—C20	118.7 (3)	O7—C19—C11	125.7 (4)
C11—N2—C8	110.8 (3)	O8—C19—C11	109.1 (3)
C11—N2—H1	111 (3)	O5—C16—O6	125.6 (4)
C8—N2—H1	117 (3)	O5—C16—C11	124.8 (4)
C12—C9—C10	112.6 (3)	O6—C16—C11	109.6 (3)
C12—C9—C8	116.3 (3)	C4—C3—C2	119.4 (4)
C10—C9—C8	105.3 (3)	C4—C3—H3	120.3
C12—C9—H9	107.4	C2—C3—H3	120.3
C10—C9—H9	107.4	O3—C14—O4	124.9 (4)
C8—C9—H9	107.4	O3—C14—C10	125.1 (4)
C16—O6—C17	119.1 (3)	O4—C14—C10	110.0 (4)
C14—O4—C15	111.1 (4)	O2—C13—H13A	109.5
C6—C5—C4	118.4 (3)	O2—C13—H13B	109.5
C6—C5—C8	122.7 (3)	H13A—C13—H13B	109.5
C4—C5—C8	118.8 (3)	O2—C13—H13C	109.5
C7—C2—C3	120.0 (3)	H13A—C13—H13C	109.5
C7—C2—C1	121.1 (3)	H13B—C13—H13C	109.5
C3—C2—C1	118.9 (4)	C21—C20—O8	108.8 (4)
N2—C8—C5	111.2 (3)	C21—C20—H20A	109.9
N2—C8—C9	103.7 (3)	O8—C20—H20A	109.9
C5—C8—C9	113.7 (3)	C21—C20—H20B	109.9
N2—C8—H8	109.4	O8—C20—H20B	109.9
C5—C8—H8	109.4	H20A—C20—H20B	108.3
C9—C8—H8	109.4	C18—C17—O6	108.9 (5)
O1—C12—O2	123.0 (3)	C18—C17—H17A	109.9
O1—C12—C9	125.2 (3)	O6—C17—H17A	109.9
O2—C12—C9	111.8 (3)	C18—C17—H17B	109.9
C7—C6—C5	121.5 (3)	O6—C17—H17B	109.9
C7—C6—H6	119.3	H17A—C17—H17B	108.3
C5—C6—H6	119.3	O4—C15—H15A	109.5
C9—C10—C11	101.9 (3)	O4—C15—H15B	109.5
C9—C10—C14	108.6 (3)	H15A—C15—H15B	109.5
C11—C10—C14	116.3 (3)	O4—C15—H15C	109.5
C9—C10—H10	109.9	H15A—C15—H15C	109.5
C11—C10—H10	109.9	H15B—C15—H15C	109.5
C14—C10—H10	109.9	C20—C21—H21A	109.5
C3—C4—C5	120.8 (3)	C20—C21—H21B	109.5
C3—C4—H4	119.6	H21A—C21—H21B	109.5
C5—C4—H4	119.6	C20—C21—H21C	109.5
N2—C11—C19	106.1 (3)	H21A—C21—H21C	109.5
N2—C11—C10	103.2 (2)	H21B—C21—H21C	109.5
C19—C11—C10	114.6 (3)	C17—C18—H18A	109.5
N2—C11—C16	114.0 (3)	C17—C18—H18B	109.5
C19—C11—C16	108.5 (3)	H18A—C18—H18B	109.5
C10—C11—C16	110.4 (3)	C17—C18—H18C	109.5
C2—C7—C6	119.8 (3)	H18A—C18—H18C	109.5
C2—C7—H7	120.1	H18B—C18—H18C	109.5
C6—C7—H7	120.1	N1—C1—C2	178.8 (5)

C11—N2—C8—C5	−130.9 (3)	C3—C2—C7—C6	1.3 (6)
C11—N2—C8—C9	−8.3 (3)	C1—C2—C7—C6	−178.6 (4)
C6—C5—C8—N2	48.9 (4)	C5—C6—C7—C2	0.6 (6)
C4—C5—C8—N2	−133.6 (3)	C20—O8—C19—O7	−2.4 (7)
C6—C5—C8—C9	−67.7 (4)	C20—O8—C19—C11	−179.8 (4)
C4—C5—C8—C9	109.8 (4)	N2—C11—C19—O7	−106.8 (5)
C12—C9—C8—N2	−142.0 (3)	C10—C11—C19—O7	6.4 (6)
C10—C9—C8—N2	−16.5 (3)	C16—C11—C19—O7	130.3 (5)
C12—C9—C8—C5	−21.1 (4)	N2—C11—C19—O8	70.6 (4)
C10—C9—C8—C5	104.4 (3)	C10—C11—C19—O8	−176.2 (3)
C13—O2—C12—O1	−6.8 (6)	C16—C11—C19—O8	−52.3 (4)
C13—O2—C12—C9	174.4 (4)	C17—O6—C16—O5	−0.3 (7)
C10—C9—C12—O1	−2.6 (6)	C17—O6—C16—C11	−179.8 (4)
C8—C9—C12—O1	119.0 (4)	N2—C11—C16—O5	18.0 (6)
C10—C9—C12—O2	176.1 (3)	C19—C11—C16—O5	136.0 (4)
C8—C9—C12—O2	−62.2 (4)	C10—C11—C16—O5	−97.7 (5)
C4—C5—C6—C7	−1.1 (6)	N2—C11—C16—O6	−162.5 (3)
C8—C5—C6—C7	176.5 (3)	C19—C11—C16—O6	−44.5 (4)
C12—C9—C10—C11	161.4 (3)	C10—C11—C16—O6	81.8 (4)
C8—C9—C10—C11	33.7 (3)	C5—C4—C3—C2	2.3 (6)
C12—C9—C10—C14	−75.3 (4)	C7—C2—C3—C4	−2.7 (6)
C8—C9—C10—C14	157.0 (3)	C1—C2—C3—C4	177.1 (4)
C6—C5—C4—C3	−0.5 (6)	C15—O4—C14—O3	−5.2 (7)
C8—C5—C4—C3	−178.1 (4)	C15—O4—C14—C10	176.6 (4)
C8—N2—C11—C19	150.5 (3)	C9—C10—C14—O3	−22.5 (6)
C8—N2—C11—C10	29.7 (3)	C11—C10—C14—O3	91.7 (5)
C8—N2—C11—C16	−90.1 (3)	C9—C10—C14—O4	155.7 (3)
C9—C10—C11—N2	−38.3 (3)	C11—C10—C14—O4	−90.1 (4)
C14—C10—C11—N2	−156.2 (3)	C19—O8—C20—C21	−155.3 (5)
C9—C10—C11—C19	−153.2 (3)	C16—O6—C17—C18	−169.0 (6)
C14—C10—C11—C19	88.9 (4)	C7—C2—C1—N1	126 (23)
C9—C10—C11—C16	83.9 (3)	C3—C2—C1—N1	−54 (23)
C14—C10—C11—C16	−34.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N1ⁱ	0.86 (4)	2.47 (4)	3.240 (5)	148 (4)
C8—H8···O1ⁱⁱ	0.98	2.39	3.333 (4)	161 (1)
C13—H13C···O7ⁱⁱ	0.96	2.46	3.388 (6)	163
C18—H18C···O5ⁱⁱⁱ	0.96	2.55	3.453 (9)	157

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₂O₈
M_r	432.42
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	291
a, b, c (Å)	8.4720 (2), 10.3043 (2), 25.8774 (5)
V (Å³)	2259.05 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.38 × 0.30 × 0.30

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.744, 0.789
No. of measured, independent and observed [I > 2σ(I)] reflections	26556, 2565, 2050
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.141, 1.03
No. of reflections	2565
No. of parameters	288
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N1ⁱ	0.86 (4)	2.47 (4)	3.240 (5)	148 (4)
C8—H8···O1ⁱⁱ	0.98	2.39	3.333 (4)	160.6 (2)
C13—H13C···O7ⁱⁱ	0.96	2.46	3.388 (6)	162.9
C18—H18C···O5ⁱⁱⁱ	0.96	2.55	3.453 (9)	156.6

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

Acknowledgements

The author acknowledges financial support from China West Normal University (11B004).

References

Coldham, I. & Hufton, R. (2005). Chem. Rev. 105, 2765–2810. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
He, L. (2010). Acta Cryst. E66, o3205. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Pandey, G., Banerjee, P. & Gadre, S. R. (2006). Chem. Rev. 106, 4484–4517. Web of Science CrossRef PubMed CAS Google Scholar
Schreiber, S. L. (2000). Science, 287, 1964–1969. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

2,2-Di­ethyl 3,4-di­methyl 5-(4-cyano­phen­yl)pyrrolidine-2,2,3,4-tetra­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2-Diethyl 3,4-dimethyl 5-(4-cyanophenyl)pyrrolidine-2,2,3,4-tetracarboxylate