5-Methyl 3-(2-methyl-prop-3-yl) 2,6-di-methyl-4-(2-nitro-sophen-yl)pyridine-3,5-dicarboxyl-ate.

In the title compound, C(20)H(22)N(2)O(5), a photo-degradation product of the hypertension drug nisoldipine, the dihedral angle between the nitro-sophenyl ring and the pyridine ring is 75.7 (3)°. In the crystal structure, weak C-H⋯O hydrogen bonds help to establish the packing.

Related literature

For general background to nisoldipine derivatives, see: Marciniec et al. (2002 ▶).

Experimental

Crystal data

C20H22N2O5

M = 370.40

Triclinic,

a = 7.1831 (4) Å

b = 9.7819 (6) Å

c = 15.0245 (9) Å

α = 89.488 (3)°

β = 81.201 (3)°

γ = 70.625 (3)°

V = 983.19 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.42 × 0.28 × 0.22 mm

Data collection

Bruker APEX II CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.963, T max = 0.980

5353 measured reflections

3623 independent reflections

2500 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.311

S = 1.01

3623 reflections

250 parameters

H-atom parameters not refined

Δρmax = 0.81 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005088/hb5320sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005088/hb5320Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H22N2O5	Z = 2
Mr = 370.40	F(000) = 392
Triclinic, P1	Dx = 1.251 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1831 (4) Å	Cell parameters from 1617 reflections
b = 9.7819 (6) Å	θ = 2.2–24.3°
c = 15.0245 (9) Å	µ = 0.09 mm−1
α = 89.488 (3)°	T = 296 K
β = 81.201 (3)°	Block, colourless
γ = 70.625 (3)°	0.42 × 0.28 × 0.22 mm
V = 983.19 (10) Å3

Bruker APEX II CCD diffractometer	3623 independent reflections
Radiation source: fine-focus sealed tube	2500 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
Tmin = 0.963, Tmax = 0.980	k = −11→11
5353 measured reflections	l = −15→18

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.311	H-atom parameters not refined
S = 1.01	w = 1/[σ2(Fo2) + (0.240P)2] where P = (Fo2 + 2Fc2)/3
3623 reflections	(Δ/σ)max < 0.001
250 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
C1	0.6145 (4)	0.4193 (3)	0.3529 (2)	0.0509 (7)
C2	0.7137 (5)	0.5026 (4)	0.3888 (2)	0.0619 (8)
H2	0.6424	0.5893	0.4215	0.074*
C3	0.9183 (5)	0.4525 (4)	0.3742 (2)	0.0686 (10)
H3	0.9872	0.5068	0.3963	0.082*
C4	1.0230 (5)	0.3236 (4)	0.3276 (2)	0.0655 (9)
H4	1.1620	0.2908	0.3190	0.079*
C5	0.9240 (4)	0.2413 (4)	0.2931 (2)	0.0597 (8)
H5	0.9969	0.1538	0.2615	0.072*
C6	0.7173 (4)	0.2887 (3)	0.30541 (18)	0.0471 (7)
C7	0.6111 (4)	0.2014 (3)	0.26614 (18)	0.0486 (7)
C8	0.5973 (4)	0.0750 (3)	0.30544 (19)	0.0493 (7)
C9	0.5000 (5)	−0.0045 (3)	0.2660 (2)	0.0573 (8)
C10	0.4346 (5)	0.1561 (4)	0.1519 (2)	0.0624 (8)
C11	0.5245 (5)	0.2442 (3)	0.1897 (2)	0.0589 (8)
C12	0.6737 (4)	0.0337 (3)	0.3918 (2)	0.0527 (7)
C13	0.8802 (7)	−0.1539 (4)	0.4692 (3)	0.0913 (13)
H13A	0.8912	−0.0762	0.5043	0.137*
H13B	1.0089	−0.2278	0.4550	0.137*
H13C	0.7878	−0.1942	0.5030	0.137*
C14	0.4632 (7)	−0.1378 (4)	0.3078 (3)	0.0812 (11)
H14A	0.3521	−0.1524	0.2859	0.122*
H14B	0.4338	−0.1233	0.3722	0.122*
H14C	0.5803	−0.2214	0.2915	0.122*
C15	0.3426 (7)	0.1944 (5)	0.0689 (3)	0.0908 (13)
H15A	0.3202	0.1112	0.0453	0.136*
H15B	0.4307	0.2246	0.0246	0.136*
H15C	0.2174	0.2720	0.0831	0.136*
C16	0.5224 (5)	0.3875 (4)	0.1491 (2)	0.0652 (9)
C17	0.3105 (6)	0.6240 (4)	0.1237 (3)	0.0798 (11)
H17A	0.3503	0.6115	0.0589	0.096*
H17B	0.3922	0.6714	0.1479	0.096*
C18	0.0950 (7)	0.7135 (4)	0.1464 (3)	0.0862 (12)
H18	0.0635	0.7300	0.2120	0.103*
C19	−0.0422 (8)	0.6433 (6)	0.1188 (4)	0.1166 (18)
H19A	−0.0070	0.6179	0.0554	0.175*
H19B	−0.1771	0.7092	0.1313	0.175*
H19C	−0.0314	0.5573	0.1519	0.175*
C20	0.0630 (9)	0.8621 (5)	0.1047 (4)	0.1198 (18)
H20A	0.1012	0.8489	0.0404	0.180*
H20B	0.1431	0.9096	0.1287	0.180*
H20C	−0.0755	0.9207	0.1188	0.180*
N1	0.4005 (4)	0.4598 (3)	0.36627 (18)	0.0646 (8)
N2	0.4221 (4)	0.0355 (3)	0.19043 (18)	0.0635 (7)
O1	0.3121 (4)	0.5800 (3)	0.4003 (2)	0.0954 (10)
O2	0.3373 (4)	0.4833 (3)	0.16329 (17)	0.0769 (8)
O3	0.6613 (4)	0.4107 (3)	0.1127 (2)	0.0913 (9)
O4	0.6244 (4)	0.1108 (2)	0.45823 (15)	0.0714 (7)
O5	0.8089 (4)	−0.0987 (2)	0.38649 (16)	0.0771 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0461 (15)	0.0539 (16)	0.0569 (16)	−0.0199 (13)	−0.0133 (12)	0.0081 (13)
C2	0.069 (2)	0.0572 (18)	0.0674 (19)	−0.0264 (15)	−0.0207 (16)	0.0038 (14)
C3	0.067 (2)	0.082 (2)	0.076 (2)	−0.0430 (18)	−0.0258 (17)	0.0156 (18)
C4	0.0428 (16)	0.083 (2)	0.078 (2)	−0.0264 (16)	−0.0173 (15)	0.0088 (18)
C5	0.0468 (16)	0.0646 (19)	0.0653 (18)	−0.0144 (14)	−0.0108 (14)	0.0018 (14)
C6	0.0467 (15)	0.0532 (16)	0.0468 (14)	−0.0213 (12)	−0.0142 (12)	0.0114 (12)
C7	0.0434 (14)	0.0519 (16)	0.0500 (15)	−0.0143 (12)	−0.0095 (12)	0.0033 (12)
C8	0.0463 (15)	0.0454 (15)	0.0526 (15)	−0.0094 (12)	−0.0104 (12)	0.0016 (12)
C9	0.0680 (19)	0.0475 (16)	0.0566 (17)	−0.0188 (14)	−0.0123 (14)	0.0018 (13)
C10	0.069 (2)	0.067 (2)	0.0594 (18)	−0.0290 (16)	−0.0223 (15)	0.0063 (15)
C11	0.0603 (18)	0.0646 (19)	0.0587 (17)	−0.0262 (15)	−0.0180 (14)	0.0102 (14)
C12	0.0525 (16)	0.0487 (16)	0.0580 (17)	−0.0183 (13)	−0.0093 (13)	0.0062 (13)
C13	0.102 (3)	0.075 (2)	0.086 (3)	−0.001 (2)	−0.046 (2)	0.018 (2)
C14	0.118 (3)	0.066 (2)	0.078 (2)	−0.048 (2)	−0.032 (2)	0.0136 (17)
C15	0.135 (4)	0.091 (3)	0.074 (2)	−0.057 (3)	−0.056 (2)	0.020 (2)
C16	0.069 (2)	0.084 (2)	0.0529 (17)	−0.0330 (19)	−0.0217 (16)	0.0143 (16)
C17	0.096 (3)	0.069 (2)	0.081 (2)	−0.030 (2)	−0.027 (2)	0.0173 (18)
C18	0.094 (3)	0.067 (2)	0.093 (3)	−0.015 (2)	−0.030 (2)	0.0032 (19)
C19	0.104 (4)	0.104 (4)	0.146 (5)	−0.031 (3)	−0.043 (3)	0.018 (3)
C20	0.139 (5)	0.073 (3)	0.144 (5)	−0.022 (3)	−0.041 (4)	0.015 (3)
N1	0.0495 (15)	0.0658 (17)	0.0748 (17)	−0.0131 (12)	−0.0125 (13)	−0.0023 (14)
N2	0.0762 (18)	0.0596 (16)	0.0632 (16)	−0.0274 (13)	−0.0253 (13)	0.0026 (12)
O1	0.0593 (15)	0.0809 (18)	0.132 (2)	−0.0068 (13)	−0.0088 (16)	−0.0327 (17)
O2	0.0765 (17)	0.0701 (15)	0.0836 (17)	−0.0239 (13)	−0.0133 (13)	0.0226 (12)
O3	0.0819 (18)	0.114 (2)	0.0919 (19)	−0.0493 (16)	−0.0209 (15)	0.0420 (17)
O4	0.0996 (19)	0.0565 (14)	0.0532 (13)	−0.0172 (12)	−0.0177 (12)	0.0036 (10)
O5	0.0776 (16)	0.0629 (14)	0.0695 (14)	0.0105 (12)	−0.0246 (12)	0.0006 (11)

C1—C2	1.405 (4)	C13—H13A	0.9600
C1—N1	1.436 (4)	C13—H13B	0.9600
C1—C6	1.384 (4)	C13—H13C	0.9600
C2—C3	1.369 (5)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.368 (5)	C14—H14C	0.9600
C3—H3	0.9300	C15—H15A	0.9601
C4—C5	1.387 (5)	C15—H15B	0.9601
C4—H4	0.9300	C15—H15C	0.9601
C5—C6	1.383 (4)	C16—O3	1.152 (4)
C5—H5	0.9300	C16—O2	1.335 (4)
C6—C7	1.496 (4)	C17—O2	1.458 (4)
C7—C11	1.386 (4)	C17—C18	1.491 (6)
C7—C8	1.392 (4)	C17—H17A	0.9700
C8—C9	1.393 (4)	C17—H17B	0.9700
C8—C12	1.487 (4)	C18—C19	1.481 (7)
C9—N2	1.340 (4)	C18—C20	1.538 (6)
C9—C14	1.525 (4)	C18—H18	0.9800
C10—N2	1.333 (4)	C19—H19A	0.9600
C10—C11	1.404 (4)	C19—H19B	0.9600
C10—C15	1.487 (4)	C19—H19C	0.9600
C11—C16	1.520 (4)	C20—H20A	0.9600
C12—O4	1.191 (4)	C20—H20B	0.9600
C12—O5	1.331 (4)	C20—H20C	0.9600
C13—O5	1.448 (4)	N1—O1	1.210 (4)
C2—C1—N1	122.6 (3)	C9—C14—H14B	109.5
C2—C1—C6	122.0 (3)	H14A—C14—H14B	109.5
N1—C1—C6	115.3 (2)	C9—C14—H14C	109.5
C3—C2—C1	118.0 (3)	H14A—C14—H14C	109.5
C3—C2—H2	121.0	H14B—C14—H14C	109.5
C1—C2—H2	121.0	C10—C15—H15A	109.5
C2—C3—C4	120.9 (3)	C10—C15—H15B	109.5
C2—C3—H3	119.6	H15A—C15—H15B	109.5
C4—C3—H3	119.5	C10—C15—H15C	109.4
C3—C4—C5	120.7 (3)	H15A—C15—H15C	109.5
C3—C4—H4	119.8	H15B—C15—H15C	109.5
C5—C4—H4	119.6	O3—C16—O2	125.0 (3)
C6—C5—C4	120.3 (3)	O3—C16—C11	124.8 (3)
C6—C5—H5	119.9	O2—C16—C11	110.2 (3)
C4—C5—H5	119.8	O2—C17—C18	107.9 (3)
C5—C6—C1	118.1 (3)	O2—C17—H17A	110.2
C5—C6—C7	120.1 (3)	C18—C17—H17A	110.2
C1—C6—C7	121.8 (2)	O2—C17—H17B	110.1
C11—C7—C8	118.4 (3)	C18—C17—H17B	110.0
C11—C7—C6	120.8 (3)	H17A—C17—H17B	108.5
C8—C7—C6	120.8 (2)	C19—C18—C17	113.8 (4)
C9—C8—C7	119.0 (3)	C19—C18—C20	111.3 (4)
C9—C8—C12	121.5 (3)	C17—C18—C20	108.8 (4)
C7—C8—C12	119.3 (2)	C19—C18—H18	107.5
N2—C9—C8	122.1 (3)	C17—C18—H18	107.6
N2—C9—C14	114.9 (3)	C20—C18—H18	107.6
C8—C9—C14	122.9 (3)	C18—C19—H19A	109.4
N2—C10—C11	121.4 (3)	C18—C19—H19B	109.5
N2—C10—C15	116.5 (3)	H19A—C19—H19B	109.5
C11—C10—C15	122.1 (3)	C18—C19—H19C	109.6
C7—C11—C10	119.4 (3)	H19A—C19—H19C	109.5
C7—C11—C16	119.9 (3)	H19B—C19—H19C	109.5
C10—C11—C16	120.7 (3)	C18—C20—H20A	109.4
O4—C12—O5	123.1 (3)	C18—C20—H20B	109.3
O4—C12—C8	124.3 (3)	H20A—C20—H20B	109.5
O5—C12—C8	112.5 (2)	C18—C20—H20C	109.7
O5—C13—H13A	109.5	H20A—C20—H20C	109.5
O5—C13—H13B	109.5	H20B—C20—H20C	109.5
H13A—C13—H13B	109.5	O1—N1—C1	114.7 (3)
O5—C13—H13C	109.4	C10—N2—C9	119.6 (3)
H13A—C13—H13C	109.5	C16—O2—C17	116.4 (3)
H13B—C13—H13C	109.5	C12—O5—C13	116.7 (3)
C9—C14—H14A	109.4

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O1i	0.96	2.39	3.344 (5)	172
C14—H14B···O4ii	0.96	2.52	3.472 (5)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O1i	0.96	2.39	3.344 (5)	172
C14—H14B⋯O4ii	0.96	2.52	3.472 (5)	174

Symmetry codes: (i) ; (ii) .