(4RS)-3-Benzyl 5-methyl 2,6-dimethyl-4-(4-nitro­phen­yl)-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

Zhang, B.; Wang, Y.; Sun, F.; Zhang, X.; Wang, W.

doi:10.1107/S1600536809049435

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3199

doi:10.1107/S1600536809049435

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(4RS)-3-Benzyl 5-methyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Bing-zhu Zhang,^a,^b Yan-ji Wang,^c Feng-xia Sun,^b ^* Xu Zhang ^b and Wei Wang ^b

^aCollege of Chemical Engineering, Hebei University of Technology, Tianjin 300130, People's Republic of China, ^bCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China, and ^cHebei University of Technology, Tianjin 300130, People's Republic of China
^*Correspondence e-mail: fxsun001@163.com

(Received 18 August 2009; accepted 19 November 2009; online 25 November 2009)

In the title compound, C₂₃H₂₂N₂O₆, the crystal packing is stabilized by intermolecular N—H⋯O hydrogen bonds, which link the molecules into chains running parallel to the c axis. Intermolecular C—H⋯O hydrogen bonds are also present in the structure.

Related literature

The title compound is a nefidipine analogue. For the use of nefidipine-type 4-aryl-1,4-dihydropyridine-3,5-dicarboxylic diesters in the treatment of cardiovascular disease, see: Goldmann & Stoltefuss (1991 ); Yiu & Knaus (1999 ). For the structure of 5-ethoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic anhydride ethyl acetate solvate, see: Sun et al. (2006 ). For hydrogen-bond motifs, see: Etter et al. (1990 ).

Experimental

Crystal data

C₂₃H₂₂N₂O₆
M_r = 422.43
Monoclinic, P 2₁ /n
a = 9.6527 (19) Å
b = 11.043 (2) Å
c = 19.883 (4) Å
β = 100.23 (3)°
V = 2085.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.26 × 0.20 × 0.10 mm

Data collection

Rigaku MM007 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.975, T_max = 0.990
16526 measured reflections
4745 independent reflections
3087 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.188
S = 1.02
4745 reflections
288 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 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
N1—H1⋯O1ⁱ	0.89 (2)	2.13 (3)	3.003 (2)	167 (2)
C15—H15⋯O4ⁱⁱ	0.93	2.43	3.303 (3)	157
C7—H7B⋯O1ⁱ	0.96	2.55	3.436 (3)	154
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049435/fb2168sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049435/fb2168Isup2.hkl

checkCIF report

Comment top

4-Aryl-1,4-dihydropyridine-3,5-dicarboxylic diesters of the nefidipine type have become almost indispensable for the treatment of cardiovascular diseases since they first appeared on the market in 1975 (Yiu & Knaus, 1999; Goldmann & Stoltefuss, 1991). The structure of the title compound, 2,6-dimethyl-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3,5 -dicarboxylic acid 3-benzyl ester 5-methyl ester, is a nefidipine analogue.

Fig. 1 shows the title molecule. In the dihydropyridine ring, the atom C4 is displaced from the mean plane formed by the remaining atoms of the same ring by 0.312 (1) Å. The dihedral angle between the C10//C11//C12//C13//C14//C15 benzene ring and the N1//C2//C3//C5//C6 plane is 89.26 (1)°. This value corresponds well to the structure of 5-ethoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3- carboxylic anhydride ethyl acetate solvate (Sun & Yu, 2006).

The intermolecular N—H···O hydrogen bonds link the molecules along c axis. The graph set is C(7) (Etter et al., 1990).

Related literature top

The title compound is a nefidipine analogue. For the use of nefidipine-type 4-aryl-1,4-dihydropyridine-3,5-dicarboxylic diesters in the treatment of cardiovascular disease, see: Goldmann & Stoltefuss (1991); Yiu & Knaus (1999). For the structure of 5-ethoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic anhydride ethyl acetate solvate, see: Sun et al. (2006). For hydrogen-bond motifs, see: Etter et al. (1990).

Experimental top

2,6-Dimethyl-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid monoethyl ester (332 mg, 1 mmol) and dicyclohexyl-carbodiimide (206 mg, 1 mmol) were dissolved in 28 ml of CH₂Cl₂. Phenyl methanol (108 mg, 1 mmol) was added dropwise to the solution at 278 K. The reaction mixture was stirred at 276-279 K for further 9 h. The solvent CH₂Cl₂ was removed by evaporation in vacuum at 293 K. The product was purified by chromatography on a silica gel column (eluted by ethyl acetate and petroleum, 1:5) at room temperature. The purified product weighted 350 mg with the yield 83%. Yellow block crystals were obtained by slow evaporation from a solution of ethyl acetate and methanol (1:1) at room temperature.

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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title molecule. The displacement ellipsoids are drawn at the 30% probability level. The H atoms are represented by spheres of arbitrary radii.

(4RS)-3-Benzyl 5-methyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate top

Crystal data top

C₂₃H₂₂N₂O₆	F(000) = 888
M_r = 422.43	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 470.0–471.0 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.6527 (19) Å	Cell parameters from 4898 reflections
b = 11.043 (2) Å	θ = 2.1–27.5°
c = 19.883 (4) Å	µ = 0.10 mm⁻¹
β = 100.23 (3)°	T = 293 K
V = 2085.9 (7) Å³	Block, yellow
Z = 4	0.26 × 0.20 × 0.10 mm

Data collection top

Rigaku MM007 diffractometer	4745 independent reflections
Radiation source: rotating anode	3087 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.040
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
ω and ϕ scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→14
T_min = 0.975, T_max = 0.990	l = −25→25
16526 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.188	w = 1/[σ²(F_o²) + (0.1057P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.002
4745 reflections	Δρ_max = 0.30 e Å⁻³
288 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
81 constraints	Extinction coefficient: 0.045 (6)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₃H₂₂N₂O₆	V = 2085.9 (7) Å³
M_r = 422.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6527 (19) Å	µ = 0.10 mm⁻¹
b = 11.043 (2) Å	T = 293 K
c = 19.883 (4) Å	0.26 × 0.20 × 0.10 mm
β = 100.23 (3)°

Data collection top

Rigaku MM007 diffractometer	4745 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3087 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.990	R_int = 0.040
16526 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.30 e Å⁻³
4745 reflections	Δρ_min = −0.20 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
O1	0.89299 (15)	0.58542 (14)	0.20521 (9)	0.0717 (5)
O2	0.78376 (14)	0.54481 (13)	0.09912 (8)	0.0653 (5)
O3	0.2026 (3)	0.23247 (18)	0.15616 (13)	0.1172 (8)
O4	0.14892 (19)	0.35571 (16)	0.23061 (10)	0.0839 (5)
O5	0.38588 (17)	0.74335 (14)	−0.02349 (8)	0.0739 (5)
O6	0.31955 (14)	0.92631 (12)	0.00562 (7)	0.0554 (4)
N1	0.61176 (17)	0.88992 (16)	0.19025 (9)	0.0534 (5)
N2	0.21172 (19)	0.33054 (17)	0.18454 (11)	0.0637 (5)
C1	0.8265 (2)	0.8162 (2)	0.25856 (12)	0.0705 (7)
H1A	0.8042	0.7733	0.2973	0.106*
H1B	0.8365	0.9009	0.2691	0.106*
H1C	0.9130	0.7857	0.2478	0.106*
C2	0.70961 (19)	0.79849 (18)	0.19804 (10)	0.0500 (5)
C3	0.69608 (18)	0.70649 (16)	0.15252 (9)	0.0456 (5)
C4	0.56533 (18)	0.69660 (15)	0.09720 (9)	0.0435 (4)
H4	0.5945	0.6705	0.0547	0.052*
C5	0.49105 (18)	0.81767 (15)	0.08450 (9)	0.0444 (4)
C6	0.51034 (19)	0.90593 (16)	0.13245 (10)	0.0463 (5)
C7	0.4354 (2)	1.02481 (18)	0.13165 (12)	0.0607 (6)
H7A	0.4610	1.0756	0.0966	0.091*
H7B	0.4616	1.0637	0.1752	0.091*
H7C	0.3356	1.0114	0.1226	0.091*
C8	0.8009 (2)	0.60980 (17)	0.15669 (11)	0.0524 (5)
C9	0.8818 (3)	0.4482 (2)	0.09446 (17)	0.0889 (9)
H9A	0.9751	0.4808	0.0986	0.133*
H9B	0.8566	0.4083	0.0511	0.133*
H9C	0.8790	0.3910	0.1306	0.133*
C10	0.46877 (17)	0.59917 (15)	0.11870 (9)	0.0421 (4)
C11	0.4607 (2)	0.48421 (17)	0.09037 (10)	0.0503 (5)
H11	0.5129	0.4664	0.0565	0.060*
C12	0.3770 (2)	0.39576 (17)	0.11132 (11)	0.0542 (5)
H12	0.3721	0.3189	0.0919	0.065*
C13	0.30103 (19)	0.42372 (17)	0.16151 (10)	0.0493 (5)
C14	0.3074 (2)	0.53621 (18)	0.19149 (12)	0.0591 (6)
H14	0.2558	0.5530	0.2257	0.071*
C15	0.3917 (2)	0.62377 (17)	0.16985 (11)	0.0555 (5)
H15	0.3969	0.7002	0.1898	0.067*
C16	0.3957 (2)	0.82418 (16)	0.01799 (10)	0.0486 (5)
C17	0.2198 (2)	0.92855 (19)	−0.05783 (11)	0.0602 (6)
H17A	0.1611	0.8567	−0.0612	0.072*
H17B	0.2699	0.9284	−0.0960	0.072*
C18	0.1296 (2)	1.03911 (19)	−0.06098 (11)	0.0567 (5)
C19	0.0127 (2)	1.0456 (2)	−0.11286 (14)	0.0782 (7)
H19	−0.0074	0.9821	−0.1438	0.094*
C20	−0.0742 (3)	1.1467 (3)	−0.11858 (17)	0.0891 (9)
H20	−0.1521	1.1502	−0.1536	0.107*
C21	−0.0473 (2)	1.2403 (2)	−0.07396 (15)	0.0808 (8)
H21	−0.1062	1.3076	−0.0783	0.097*
C22	0.0669 (3)	1.2349 (2)	−0.02266 (14)	0.0790 (7)
H22	0.0855	1.2983	0.0084	0.095*
C23	0.1556 (2)	1.1348 (2)	−0.01659 (12)	0.0680 (6)
H23	0.2339	1.1327	0.0182	0.082*
H1	0.622 (2)	0.952 (2)	0.2186 (12)	0.068 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0723 (9)	0.0628 (10)	0.0728 (11)	0.0165 (8)	−0.0062 (8)	0.0123 (8)
O2	0.0582 (8)	0.0574 (9)	0.0780 (11)	0.0130 (7)	0.0060 (7)	−0.0124 (8)
O3	0.160 (2)	0.0591 (12)	0.151 (2)	−0.0422 (12)	0.0787 (17)	−0.0187 (12)
O4	0.0931 (12)	0.0766 (12)	0.0923 (14)	−0.0070 (9)	0.0443 (11)	0.0172 (9)
O5	0.0962 (11)	0.0602 (10)	0.0566 (9)	0.0213 (9)	−0.0106 (8)	−0.0152 (7)
O6	0.0631 (8)	0.0441 (8)	0.0538 (8)	0.0061 (6)	−0.0039 (6)	−0.0001 (6)
N1	0.0600 (10)	0.0466 (10)	0.0499 (10)	0.0026 (8)	−0.0004 (8)	−0.0076 (8)
N2	0.0698 (11)	0.0484 (11)	0.0754 (13)	−0.0024 (9)	0.0195 (10)	0.0131 (9)
C1	0.0691 (13)	0.0687 (15)	0.0658 (14)	0.0023 (12)	−0.0100 (11)	−0.0061 (12)
C2	0.0527 (10)	0.0487 (11)	0.0476 (11)	−0.0023 (9)	0.0059 (8)	0.0020 (8)
C3	0.0485 (10)	0.0413 (10)	0.0474 (10)	−0.0005 (8)	0.0093 (8)	0.0040 (8)
C4	0.0501 (10)	0.0389 (9)	0.0424 (10)	0.0019 (8)	0.0103 (8)	0.0010 (8)
C5	0.0496 (10)	0.0372 (9)	0.0460 (10)	−0.0009 (8)	0.0074 (8)	0.0013 (8)
C6	0.0526 (10)	0.0382 (9)	0.0478 (10)	−0.0007 (8)	0.0079 (8)	0.0000 (8)
C7	0.0724 (13)	0.0434 (11)	0.0625 (13)	0.0050 (9)	0.0020 (10)	−0.0086 (9)
C8	0.0541 (11)	0.0433 (11)	0.0591 (12)	−0.0026 (9)	0.0084 (9)	0.0058 (9)
C9	0.0723 (15)	0.0665 (16)	0.126 (3)	0.0215 (13)	0.0130 (16)	−0.0199 (16)
C10	0.0465 (9)	0.0378 (9)	0.0414 (9)	0.0051 (8)	0.0059 (7)	0.0014 (7)
C11	0.0637 (12)	0.0423 (10)	0.0468 (11)	−0.0006 (9)	0.0147 (9)	−0.0060 (8)
C12	0.0700 (12)	0.0377 (10)	0.0563 (12)	−0.0033 (9)	0.0148 (10)	−0.0064 (9)
C13	0.0518 (10)	0.0421 (10)	0.0544 (11)	−0.0004 (8)	0.0106 (9)	0.0082 (8)
C14	0.0694 (13)	0.0478 (11)	0.0670 (14)	0.0027 (10)	0.0311 (11)	−0.0010 (10)
C15	0.0709 (12)	0.0385 (10)	0.0622 (13)	−0.0008 (9)	0.0255 (10)	−0.0089 (9)
C16	0.0574 (11)	0.0388 (10)	0.0490 (11)	0.0010 (9)	0.0079 (9)	−0.0004 (8)
C17	0.0665 (12)	0.0573 (13)	0.0514 (12)	0.0026 (10)	−0.0045 (10)	0.0010 (10)
C18	0.0542 (11)	0.0551 (12)	0.0588 (12)	−0.0015 (9)	0.0048 (9)	0.0132 (10)
C19	0.0733 (15)	0.0717 (16)	0.0805 (17)	−0.0048 (13)	−0.0107 (13)	0.0083 (13)
C20	0.0638 (14)	0.0880 (19)	0.105 (2)	0.0088 (14)	−0.0128 (14)	0.0223 (17)
C21	0.0667 (15)	0.0744 (17)	0.099 (2)	0.0178 (13)	0.0083 (14)	0.0191 (15)
C22	0.0870 (17)	0.0657 (15)	0.0821 (18)	0.0202 (14)	0.0090 (14)	0.0014 (13)
C23	0.0690 (13)	0.0630 (14)	0.0666 (15)	0.0106 (11)	−0.0021 (11)	0.0033 (11)

Geometric parameters (Å, º) top

O1—C8	1.220 (2)	C9—H9A	0.9600
O2—C8	1.336 (3)	C9—H9B	0.9600
O2—C9	1.440 (2)	C9—H9C	0.9600
O3—N2	1.217 (3)	C10—C11	1.385 (2)
O4—N2	1.217 (3)	C10—C15	1.390 (3)
O5—C16	1.208 (2)	C11—C12	1.378 (3)
O6—C16	1.345 (2)	C11—H11	0.9300
O6—C17	1.445 (2)	C12—C13	1.375 (3)
N1—C2	1.372 (3)	C12—H12	0.9300
N1—C6	1.382 (2)	C13—C14	1.375 (3)
N1—H1	0.89 (2)	C14—C15	1.381 (3)
N2—C13	1.467 (3)	C14—H14	0.9300
C1—C2	1.509 (3)	C15—H15	0.9300
C1—H1A	0.9600	C17—C18	1.495 (3)
C1—H1B	0.9600	C17—H17A	0.9700
C1—H1C	0.9600	C17—H17B	0.9700
C2—C3	1.352 (3)	C18—C23	1.371 (3)
C3—C8	1.463 (3)	C18—C19	1.389 (3)
C3—C4	1.524 (2)	C19—C20	1.389 (4)
C4—C5	1.517 (2)	C19—H19	0.9300
C4—C10	1.533 (2)	C20—C21	1.357 (4)
C4—H4	0.9800	C20—H20	0.9300
C5—C6	1.353 (3)	C21—C22	1.364 (4)
C5—C16	1.473 (3)	C21—H21	0.9300
C6—C7	1.498 (3)	C22—C23	1.391 (3)
C7—H7A	0.9600	C22—H22	0.9300
C7—H7B	0.9600	C23—H23	0.9300
C7—H7C	0.9600

C8—O2—C9	118.08 (18)	H9B—C9—H9C	109.5
C16—O6—C17	115.58 (14)	C11—C10—C15	118.56 (17)
C2—N1—C6	124.02 (17)	C11—C10—C4	121.51 (17)
C2—N1—H1	120.4 (14)	C15—C10—C4	119.87 (16)
C6—N1—H1	114.2 (14)	C12—C11—C10	121.33 (18)
O4—N2—O3	123.2 (2)	C12—C11—H11	119.3
O4—N2—C13	118.27 (19)	C10—C11—H11	119.3
O3—N2—C13	118.5 (2)	C13—C12—C11	118.50 (18)
C2—C1—H1A	109.5	C13—C12—H12	120.7
C2—C1—H1B	109.5	C11—C12—H12	120.7
H1A—C1—H1B	109.5	C14—C13—C12	121.97 (18)
C2—C1—H1C	109.5	C14—C13—N2	118.81 (19)
H1A—C1—H1C	109.5	C12—C13—N2	119.21 (18)
H1B—C1—H1C	109.5	C13—C14—C15	118.75 (19)
C3—C2—N1	119.65 (17)	C13—C14—H14	120.6
C3—C2—C1	126.96 (18)	C15—C14—H14	120.6
N1—C2—C1	113.36 (17)	C14—C15—C10	120.87 (18)
C2—C3—C8	121.81 (17)	C14—C15—H15	119.6
C2—C3—C4	120.43 (16)	C10—C15—H15	119.6
C8—C3—C4	117.66 (16)	O5—C16—O6	121.41 (17)
C5—C4—C3	111.31 (14)	O5—C16—C5	122.53 (17)
C5—C4—C10	111.85 (14)	O6—C16—C5	116.06 (15)
C3—C4—C10	108.40 (14)	O6—C17—C18	110.09 (17)
C5—C4—H4	108.4	O6—C17—H17A	109.6
C3—C4—H4	108.4	C18—C17—H17A	109.6
C10—C4—H4	108.4	O6—C17—H17B	109.6
C6—C5—C16	125.68 (16)	C18—C17—H17B	109.6
C6—C5—C4	121.06 (16)	H17A—C17—H17B	108.2
C16—C5—C4	113.21 (15)	C23—C18—C19	118.0 (2)
C5—C6—N1	118.83 (16)	C23—C18—C17	124.32 (18)
C5—C6—C7	128.20 (17)	C19—C18—C17	117.6 (2)
N1—C6—C7	112.97 (16)	C20—C19—C18	120.1 (2)
C6—C7—H7A	109.5	C20—C19—H19	120.0
C6—C7—H7B	109.5	C18—C19—H19	120.0
H7A—C7—H7B	109.5	C21—C20—C19	121.1 (2)
C6—C7—H7C	109.5	C21—C20—H20	119.5
H7A—C7—H7C	109.5	C19—C20—H20	119.5
H7B—C7—H7C	109.5	C20—C21—C22	119.4 (2)
O1—C8—O2	121.37 (18)	C20—C21—H21	120.3
O1—C8—C3	127.2 (2)	C22—C21—H21	120.3
O2—C8—C3	111.38 (16)	C21—C22—C23	120.2 (2)
O2—C9—H9A	109.5	C21—C22—H22	119.9
O2—C9—H9B	109.5	C23—C22—H22	119.9
H9A—C9—H9B	109.5	C18—C23—C22	121.2 (2)
O2—C9—H9C	109.5	C18—C23—H23	119.4
H9A—C9—H9C	109.5	C22—C23—H23	119.4

C6—N1—C2—C3	−10.8 (3)	C4—C10—C11—C12	178.01 (16)
C6—N1—C2—C1	167.68 (19)	C10—C11—C12—C13	−0.2 (3)
N1—C2—C3—C8	177.12 (17)	C11—C12—C13—C14	−0.6 (3)
C1—C2—C3—C8	−1.2 (3)	C11—C12—C13—N2	−179.83 (17)
N1—C2—C3—C4	−6.5 (3)	O4—N2—C13—C14	−1.7 (3)
C1—C2—C3—C4	175.23 (19)	O3—N2—C13—C14	177.4 (2)
C2—C3—C4—C5	21.3 (2)	O4—N2—C13—C12	177.56 (19)
C8—C3—C4—C5	−162.18 (16)	O3—N2—C13—C12	−3.3 (3)
C2—C3—C4—C10	−102.15 (19)	C12—C13—C14—C15	0.7 (3)
C8—C3—C4—C10	74.4 (2)	N2—C13—C14—C15	179.89 (18)
C3—C4—C5—C6	−21.9 (2)	C13—C14—C15—C10	0.1 (3)
C10—C4—C5—C6	99.5 (2)	C11—C10—C15—C14	−0.8 (3)
C3—C4—C5—C16	160.48 (16)	C4—C10—C15—C14	−178.00 (17)
C10—C4—C5—C16	−78.09 (19)	C17—O6—C16—O5	4.1 (3)
C16—C5—C6—N1	−175.08 (17)	C17—O6—C16—C5	−176.17 (17)
C4—C5—C6—N1	7.6 (3)	C6—C5—C16—O5	178.0 (2)
C16—C5—C6—C7	4.1 (3)	C4—C5—C16—O5	−4.5 (3)
C4—C5—C6—C7	−173.18 (18)	C6—C5—C16—O6	−1.8 (3)
C2—N1—C6—C5	10.3 (3)	C4—C5—C16—O6	175.70 (16)
C2—N1—C6—C7	−169.03 (19)	C16—O6—C17—C18	172.55 (17)
C9—O2—C8—O1	−3.0 (3)	O6—C17—C18—C23	11.5 (3)
C9—O2—C8—C3	178.18 (18)	O6—C17—C18—C19	−169.27 (19)
C2—C3—C8—O1	15.2 (3)	C23—C18—C19—C20	−0.2 (4)
C4—C3—C8—O1	−161.27 (19)	C17—C18—C19—C20	−179.5 (2)
C2—C3—C8—O2	−166.02 (18)	C18—C19—C20—C21	−0.2 (4)
C4—C3—C8—O2	17.5 (2)	C19—C20—C21—C22	−0.1 (4)
C5—C4—C10—C11	134.51 (18)	C20—C21—C22—C23	0.6 (4)
C3—C4—C10—C11	−102.39 (19)	C19—C18—C23—C22	0.7 (4)
C5—C4—C10—C15	−48.4 (2)	C17—C18—C23—C22	180.0 (2)
C3—C4—C10—C15	74.7 (2)	C21—C22—C23—C18	−1.0 (4)
C15—C10—C11—C12	0.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.89 (2)	2.13 (3)	3.003 (2)	167 (2)
C15—H15···O4ⁱⁱ	0.93	2.43	3.303 (3)	157
C7—H7B···O1ⁱ	0.96	2.55	3.436 (3)	154

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₂N₂O₆
M_r	422.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.6527 (19), 11.043 (2), 19.883 (4)
β (°)	100.23 (3)
V (Å³)	2085.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.26 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku MM007 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.975, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	16526, 4745, 3087
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.188, 1.02
No. of reflections	4745
No. of parameters	288
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.20

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
N1—H1···O1ⁱ	0.89 (2)	2.13 (3)	3.003 (2)	167 (2)
C15—H15···O4ⁱⁱ	0.93	2.43	3.303 (3)	156.5
C7—H7B···O1ⁱ	0.96	2.55	3.436 (3)	153.8

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

Acknowledgements

The authors gratefully acknowledge support from Nankai University and Hebei University of Science and Technology.

References

Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Goldmann, S. & Stoltefuss, J. (1991). Angew. Chem. Int. Ed. Engl. 30, 1559–1578. CrossRef Web of Science Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, F.-X., Yu, Y.-F., Guo, X.-N. & Guo, J.-Y. (2006). Acta Cryst. E62, o83–o84. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Yiu, S. H. & Knaus, E. E. (1999). Drug Dev. Res. 48, 26–37. Web of Science CrossRef CAS Google Scholar

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

(4RS)-3-Benzyl 5-methyl 2,6-di­methyl-4-(4-nitro­phen­yl)-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

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(4RS)-3-Benzyl 5-methyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate