Literature DB >> 23468809

Dimethyl 2,6-dimethyl-4-{3-[4-(methyl-sulfan-yl)phen-yl]-1H-pyrazol-4-yl}-1,4-dihydro-pyridine-3,5-dicarboxyl-ate monohydrate.

Arun M Islor¹, A M Vijesh, Thomas Gerber, Eric Hosten, Richard Betz.

Abstract

In the title compound, C21H23N3O4S·H2O, the methyl-sulfanyl group is disordered over two sets of sites with site-occupancy factors of 0.631 (11) and 0.369 (11). The dihydro-pyridine ring adopts an E4 conformation. In the crystal, classical O-H⋯N, O-H⋯O and N-H⋯O hydrogen bonds, as well as C-H⋯O and C-H⋯S contacts, connect the mol-ecules into a three-dimensional network.

Entities: CellLine Chemical Disease Gene

Year: 2012 PMID： 23468809 PMCID： PMC3588844 DOI： 10.1107/S1600536812045333

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general information about the pharmacological importance of 1,4-dihydropyridine-based drugs, see: Janis & Triggle (1983 ▶); Boecker & Guengerich (1986 ▶); Gordeev et al. (1996 ▶); Buhler & Kiowski (1987 ▶); Vo et al. (1995 ▶). For puckering analysis of cyclic motifs, see: Cremer & Pople (1975 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H23N3O4S·H2O M = 431.50 Monoclinic, a = 10.5542 (2) Å b = 14.7260 (2) Å c = 14.5377 (2) Å β = 110.106 (1)° V = 2121.77 (6) Å3 Z = 4 Mo Kα radiation μ = 0.19 mm−1 T = 200 K 0.27 × 0.23 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.950, T max = 0.963 20236 measured reflections 5267 independent reflections 4311 reflections with I > 2σ(I) R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.111 S = 1.03 5267 reflections 312 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.30 e Å−3 Δρmin = −0.27 e Å−3 Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045333/rn2110sup1.cif Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812045333/rn2110Isup2.cdx Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045333/rn2110Isup3.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812045333/rn2110Isup4.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₁H₂₃N₃O₄S·H₂O	F(000) = 912
M_r = 431.50	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 467–469 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.5542 (2) Å	Cell parameters from 9343 reflections
b = 14.7260 (2) Å	θ = 2.5–28.2°
c = 14.5377 (2) Å	µ = 0.19 mm⁻¹
β = 110.106 (1)°	T = 200 K
V = 2121.77 (6) Å³	Block, colourless
Z = 4	0.27 × 0.23 × 0.20 mm

Bruker APEXII CCD diffractometer	5267 independent reflections
Radiation source: fine-focus sealed tube	4311 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
φ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→13
T_min = 0.950, T_max = 0.963	k = −14→19
20236 measured reflections	l = −13→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.056P)² + 0.7436P] where P = (F_o² + 2F_c²)/3
5267 reflections	(Δ/σ)_max = 0.001
312 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.93564 (10)	0.59820 (7)	0.43428 (7)	0.0310 (2)
O2	0.78574 (10)	0.70794 (7)	0.42595 (7)	0.0347 (2)
O3	0.87427 (11)	0.35098 (7)	0.22830 (8)	0.0376 (3)
O4	0.69528 (12)	0.32275 (8)	0.09516 (8)	0.0422 (3)
O8	0.73981 (13)	0.12824 (12)	0.41554 (11)	0.0621 (4)
H8A	0.820 (3)	0.1239 (17)	0.4195 (18)	0.073 (7)*
H8B	0.743 (3)	0.1385 (17)	0.473 (2)	0.075 (8)*
N21	0.88151 (11)	0.65657 (8)	0.07373 (8)	0.0278 (2)
H21	0.8649 (18)	0.6971 (13)	0.0262 (13)	0.041 (5)*
N22	0.99846 (12)	0.60935 (8)	0.10597 (8)	0.0294 (3)
N31	0.51897 (12)	0.55198 (8)	0.18783 (9)	0.0286 (2)
H31A	0.431 (2)	0.5681 (12)	0.1579 (13)	0.043 (5)*
C2	0.81451 (13)	0.63803 (8)	0.39268 (9)	0.0231 (2)
C3	1.02617 (15)	0.64046 (11)	0.52148 (10)	0.0346 (3)
H3A	0.9833	0.6430	0.5715	0.052*
H3B	1.0472	0.7022	0.5061	0.052*
H3C	1.1096	0.6050	0.5463	0.052*
C4	0.75074 (14)	0.37067 (9)	0.16581 (10)	0.0270 (3)
C5	0.9362 (2)	0.27053 (11)	0.20646 (14)	0.0543 (5)
H5A	1.0260	0.2627	0.2559	0.081*
H5B	0.9444	0.2766	0.1416	0.081*
H5C	0.8803	0.2175	0.2070	0.081*
C6	0.51172 (15)	0.66544 (11)	0.30489 (12)	0.0373 (3)
H6A	0.5579	0.6767	0.3749	0.056*
H6B	0.4234	0.6380	0.2948	0.056*
H6C	0.4995	0.7230	0.2690	0.056*
C7	0.45802 (15)	0.42238 (10)	0.07938 (11)	0.0347 (3)
H7A	0.4535	0.3609	0.1038	0.052*
H7B	0.4796	0.4191	0.0191	0.052*
H7C	0.3707	0.4526	0.0658	0.052*
C11	1.10148 (13)	0.49866 (9)	0.23494 (10)	0.0267 (3)
C12	1.14884 (14)	0.49982 (10)	0.33673 (11)	0.0336 (3)
H12	1.1077	0.5389	0.3702	0.040*
C13	1.25535 (15)	0.44469 (11)	0.39020 (12)	0.0384 (3)
H13	1.2866	0.4466	0.4597	0.046*
C14	1.31631 (14)	0.38692 (10)	0.34276 (12)	0.0360 (3)
C15	1.26844 (18)	0.38458 (12)	0.24128 (13)	0.0446 (4)
H15	1.3083	0.3444	0.2079	0.054*
C16	1.16273 (17)	0.44037 (11)	0.18802 (12)	0.0398 (4)
H16	1.1319	0.4386	0.1185	0.048*
C21	0.98781 (13)	0.55804 (8)	0.17910 (9)	0.0238 (3)
C22	0.86336 (12)	0.57278 (8)	0.19351 (9)	0.0205 (2)
C23	0.79950 (13)	0.63695 (8)	0.12396 (9)	0.0239 (3)
H23	0.7131	0.6626	0.1135	0.029*
C31	0.79937 (12)	0.52258 (8)	0.25760 (8)	0.0200 (2)
H31	0.8713	0.4887	0.3095	0.024*
C32	0.72985 (12)	0.58775 (8)	0.30658 (9)	0.0217 (2)
C33	0.59493 (13)	0.60214 (9)	0.26803 (9)	0.0253 (3)
C34	0.56572 (13)	0.47545 (9)	0.15537 (9)	0.0256 (3)
C35	0.69821 (13)	0.45444 (8)	0.19347 (9)	0.0228 (2)
S1A	1.4500 (2)	0.31690 (16)	0.41722 (17)	0.0465 (5)	0.631 (11)
C1A	1.5934 (3)	0.3614 (3)	0.3947 (5)	0.0589 (14)	0.631 (11)
H1A	1.6736	0.3261	0.4315	0.088*	0.631 (11)
H1B	1.6066	0.4250	0.4156	0.088*	0.631 (11)
H1C	1.5791	0.3575	0.3245	0.088*	0.631 (11)
S1B	1.4470 (4)	0.3094 (3)	0.4019 (4)	0.0648 (12)	0.369 (11)
C1B	1.5788 (7)	0.3823 (5)	0.4539 (10)	0.069 (3)	0.369 (11)
H1D	1.6579	0.3478	0.4939	0.104*	0.369 (11)
H1E	1.5536	0.4262	0.4953	0.104*	0.369 (11)
H1F	1.6002	0.4147	0.4022	0.104*	0.369 (11)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0267 (5)	0.0338 (5)	0.0252 (5)	0.0035 (4)	−0.0004 (4)	−0.0091 (4)
O2	0.0364 (5)	0.0316 (5)	0.0311 (5)	0.0039 (4)	0.0051 (4)	−0.0119 (4)
O3	0.0451 (6)	0.0263 (5)	0.0333 (5)	0.0110 (4)	0.0031 (4)	−0.0057 (4)
O4	0.0466 (6)	0.0377 (6)	0.0384 (6)	−0.0048 (5)	0.0098 (5)	−0.0183 (5)
O8	0.0280 (6)	0.1059 (13)	0.0516 (8)	−0.0074 (7)	0.0129 (6)	−0.0297 (8)
N21	0.0281 (6)	0.0282 (6)	0.0250 (5)	0.0005 (4)	0.0065 (4)	0.0076 (5)
N22	0.0279 (6)	0.0324 (6)	0.0292 (6)	0.0028 (5)	0.0115 (5)	0.0055 (5)
N31	0.0204 (5)	0.0331 (6)	0.0287 (6)	−0.0013 (4)	0.0039 (4)	−0.0032 (5)
C2	0.0254 (6)	0.0240 (6)	0.0200 (6)	−0.0012 (5)	0.0080 (5)	−0.0011 (5)
C3	0.0311 (7)	0.0393 (8)	0.0249 (7)	−0.0018 (6)	−0.0013 (5)	−0.0074 (6)
C4	0.0353 (7)	0.0219 (6)	0.0248 (6)	−0.0045 (5)	0.0114 (5)	−0.0010 (5)
C5	0.0691 (12)	0.0330 (8)	0.0528 (10)	0.0237 (8)	0.0107 (9)	−0.0065 (8)
C6	0.0290 (7)	0.0438 (8)	0.0393 (8)	0.0073 (6)	0.0121 (6)	−0.0071 (7)
C7	0.0308 (7)	0.0377 (7)	0.0314 (7)	−0.0130 (6)	0.0052 (6)	−0.0059 (6)
C11	0.0242 (6)	0.0268 (6)	0.0304 (7)	0.0024 (5)	0.0113 (5)	0.0036 (5)
C12	0.0297 (7)	0.0388 (8)	0.0308 (7)	0.0075 (6)	0.0084 (6)	−0.0013 (6)
C13	0.0308 (7)	0.0469 (9)	0.0330 (8)	0.0058 (6)	0.0052 (6)	0.0053 (7)
C14	0.0257 (7)	0.0336 (7)	0.0481 (9)	0.0059 (6)	0.0121 (6)	0.0123 (6)
C15	0.0476 (9)	0.0418 (9)	0.0508 (10)	0.0198 (7)	0.0250 (8)	0.0076 (7)
C16	0.0461 (9)	0.0429 (8)	0.0336 (8)	0.0150 (7)	0.0180 (7)	0.0053 (7)
C21	0.0246 (6)	0.0237 (6)	0.0230 (6)	0.0007 (5)	0.0082 (5)	0.0002 (5)
C22	0.0210 (5)	0.0189 (5)	0.0198 (5)	−0.0022 (4)	0.0046 (4)	−0.0025 (4)
C23	0.0220 (6)	0.0225 (6)	0.0245 (6)	−0.0023 (5)	0.0045 (5)	−0.0003 (5)
C31	0.0212 (5)	0.0189 (5)	0.0185 (5)	−0.0008 (4)	0.0049 (4)	−0.0012 (4)
C32	0.0237 (6)	0.0213 (5)	0.0199 (6)	−0.0006 (4)	0.0070 (5)	−0.0016 (5)
C33	0.0260 (6)	0.0264 (6)	0.0240 (6)	−0.0009 (5)	0.0090 (5)	−0.0009 (5)
C34	0.0275 (6)	0.0256 (6)	0.0226 (6)	−0.0071 (5)	0.0071 (5)	−0.0006 (5)
C35	0.0278 (6)	0.0208 (6)	0.0195 (5)	−0.0053 (5)	0.0078 (5)	−0.0019 (5)
S1A	0.0298 (7)	0.0559 (11)	0.0562 (8)	0.0169 (7)	0.0179 (5)	0.0368 (7)
C1A	0.0275 (14)	0.051 (2)	0.094 (3)	−0.0008 (13)	0.0159 (17)	0.017 (2)
S1B	0.0287 (12)	0.0245 (10)	0.121 (3)	0.0001 (8)	−0.0002 (13)	−0.0005 (14)
C1B	0.033 (3)	0.053 (4)	0.101 (8)	−0.003 (2)	−0.003 (3)	0.013 (4)

O1—C2	1.3464 (16)	C11—C16	1.387 (2)
O1—C3	1.4402 (16)	C11—C12	1.390 (2)
O2—C2	1.2193 (16)	C11—C21	1.4810 (17)
O3—C4	1.3397 (17)	C12—C13	1.388 (2)
O3—C5	1.4403 (18)	C12—H12	0.9500
O4—C4	1.2175 (16)	C13—C14	1.385 (2)
O8—H8A	0.83 (3)	C13—H13	0.9500
O8—H8B	0.84 (3)	C14—C15	1.386 (2)
N21—C23	1.3417 (17)	C14—S1B	1.770 (4)
N21—N22	1.3524 (16)	C14—S1A	1.782 (3)
N21—H21	0.884 (19)	C15—C16	1.388 (2)
N22—C21	1.3402 (17)	C15—H15	0.9500
N31—C34	1.3770 (18)	C16—H16	0.9500
N31—C33	1.3802 (17)	C21—C22	1.4161 (17)
N31—H31A	0.908 (19)	C22—C23	1.3788 (17)
C2—C32	1.4644 (17)	C22—C31	1.5177 (16)
C3—H3A	0.9800	C23—H23	0.9500
C3—H3B	0.9800	C31—C32	1.5250 (16)
C3—H3C	0.9800	C31—C35	1.5270 (16)
C4—C35	1.4642 (18)	C31—H31	1.0000
C5—H5A	0.9800	C32—C33	1.3557 (18)
C5—H5B	0.9800	C34—C35	1.3511 (18)
C5—H5C	0.9800	S1A—C1A	1.780 (4)
C6—C33	1.5004 (19)	C1A—H1A	0.9800
C6—H6A	0.9800	C1A—H1B	0.9800
C6—H6B	0.9800	C1A—H1C	0.9800
C6—H6C	0.9800	S1B—C1B	1.713 (8)
C7—C34	1.5034 (17)	C1B—H1D	0.9800
C7—H7A	0.9800	C1B—H1E	0.9800
C7—H7B	0.9800	C1B—H1F	0.9800
C7—H7C	0.9800

C2—O1—C3	116.57 (10)	C12—C13—H13	119.8
C4—O3—C5	115.99 (12)	C13—C14—C15	118.92 (13)
H8A—O8—H8B	105 (2)	C13—C14—S1B	124.9 (2)
C23—N21—N22	112.54 (11)	C15—C14—S1B	116.1 (2)
C23—N21—H21	125.4 (12)	C13—C14—S1A	117.34 (15)
N22—N21—H21	122.0 (12)	C15—C14—S1A	123.72 (15)
C21—N22—N21	104.44 (11)	C14—C15—C16	120.55 (15)
C34—N31—C33	123.70 (11)	C14—C15—H15	119.7
C34—N31—H31A	118.4 (12)	C16—C15—H15	119.7
C33—N31—H31A	117.7 (12)	C11—C16—C15	120.89 (15)
O2—C2—O1	121.14 (11)	C11—C16—H16	119.6
O2—C2—C32	127.16 (12)	C15—C16—H16	119.6
O1—C2—C32	111.70 (10)	N22—C21—C22	111.46 (11)
O1—C3—H3A	109.5	N22—C21—C11	119.65 (11)
O1—C3—H3B	109.5	C22—C21—C11	128.85 (11)
H3A—C3—H3B	109.5	C23—C22—C21	103.95 (11)
O1—C3—H3C	109.5	C23—C22—C31	125.14 (11)
H3A—C3—H3C	109.5	C21—C22—C31	130.33 (11)
H3B—C3—H3C	109.5	N21—C23—C22	107.61 (11)
O4—C4—O3	121.34 (13)	N21—C23—H23	126.2
O4—C4—C35	127.04 (13)	C22—C23—H23	126.2
O3—C4—C35	111.61 (11)	C22—C31—C32	111.54 (10)
O3—C5—H5A	109.5	C22—C31—C35	108.10 (9)
O3—C5—H5B	109.5	C32—C31—C35	110.55 (10)
H5A—C5—H5B	109.5	C22—C31—H31	108.9
O3—C5—H5C	109.5	C32—C31—H31	108.9
H5A—C5—H5C	109.5	C35—C31—H31	108.9
H5B—C5—H5C	109.5	C33—C32—C2	121.32 (11)
C33—C6—H6A	109.5	C33—C32—C31	120.73 (11)
C33—C6—H6B	109.5	C2—C32—C31	117.86 (10)
H6A—C6—H6B	109.5	C32—C33—N31	119.22 (12)
C33—C6—H6C	109.5	C32—C33—C6	127.59 (12)
H6A—C6—H6C	109.5	N31—C33—C6	113.13 (12)
H6B—C6—H6C	109.5	C35—C34—N31	119.29 (11)
C34—C7—H7A	109.5	C35—C34—C7	126.64 (12)
C34—C7—H7B	109.5	N31—C34—C7	114.07 (12)
H7A—C7—H7B	109.5	C34—C35—C4	121.10 (11)
C34—C7—H7C	109.5	C34—C35—C31	120.51 (11)
H7A—C7—H7C	109.5	C4—C35—C31	118.04 (11)
H7B—C7—H7C	109.5	C1A—S1A—C14	102.77 (15)
C16—C11—C12	118.26 (13)	C1B—S1B—C14	100.9 (3)
C16—C11—C21	121.51 (12)	S1B—C1B—H1D	109.5
C12—C11—C21	120.23 (12)	S1B—C1B—H1E	109.5
C13—C12—C11	120.98 (14)	H1D—C1B—H1E	109.5
C13—C12—H12	119.5	S1B—C1B—H1F	109.5
C11—C12—H12	119.5	H1D—C1B—H1F	109.5
C14—C13—C12	120.39 (14)	H1E—C1B—H1F	109.5
C14—C13—H13	119.8

C23—N21—N22—C21	0.26 (15)	O2—C2—C32—C33	−16.9 (2)
C3—O1—C2—O2	2.32 (19)	O1—C2—C32—C33	163.70 (12)
C3—O1—C2—C32	−178.28 (11)	O2—C2—C32—C31	159.42 (13)
C5—O3—C4—O4	0.1 (2)	O1—C2—C32—C31	−19.94 (16)
C5—O3—C4—C35	−178.85 (14)	C22—C31—C32—C33	97.79 (13)
C16—C11—C12—C13	0.5 (2)	C35—C31—C32—C33	−22.52 (16)
C21—C11—C12—C13	−179.93 (13)	C22—C31—C32—C2	−78.60 (13)
C11—C12—C13—C14	−0.3 (2)	C35—C31—C32—C2	161.10 (10)
C12—C13—C14—C15	−0.5 (2)	C2—C32—C33—N31	−178.89 (11)
C12—C13—C14—S1B	−176.74 (19)	C31—C32—C33—N31	4.85 (19)
C12—C13—C14—S1A	−178.72 (14)	C2—C32—C33—C6	−1.8 (2)
C13—C14—C15—C16	1.1 (3)	C31—C32—C33—C6	−178.10 (13)
S1B—C14—C15—C16	177.66 (19)	C34—N31—C33—C32	13.4 (2)
S1A—C14—C15—C16	179.19 (15)	C34—N31—C33—C6	−164.05 (13)
C12—C11—C16—C15	0.1 (2)	C33—N31—C34—C35	−10.2 (2)
C21—C11—C16—C15	−179.48 (14)	C33—N31—C34—C7	168.98 (12)
C14—C15—C16—C11	−0.9 (3)	N31—C34—C35—C4	175.98 (11)
N21—N22—C21—C22	−0.05 (15)	C7—C34—C35—C4	−3.1 (2)
N21—N22—C21—C11	−177.88 (11)	N31—C34—C35—C31	−10.96 (18)
C16—C11—C21—N22	−49.61 (19)	C7—C34—C35—C31	169.94 (12)
C12—C11—C21—N22	130.85 (14)	O4—C4—C35—C34	16.9 (2)
C16—C11—C21—C22	132.99 (15)	O3—C4—C35—C34	−164.25 (12)
C12—C11—C21—C22	−46.5 (2)	O4—C4—C35—C31	−156.34 (14)
N22—C21—C22—C23	−0.16 (14)	O3—C4—C35—C31	22.52 (16)
C11—C21—C22—C23	177.41 (13)	C22—C31—C35—C34	−96.68 (13)
N22—C21—C22—C31	171.27 (12)	C32—C31—C35—C34	25.66 (16)
C11—C21—C22—C31	−11.2 (2)	C22—C31—C35—C4	76.59 (13)
N22—N21—C23—C22	−0.37 (15)	C32—C31—C35—C4	−161.07 (11)
C21—C22—C23—N21	0.30 (13)	C13—C14—S1A—C1A	−112.7 (3)
C31—C22—C23—N21	−171.71 (11)	C15—C14—S1A—C1A	69.2 (4)
C23—C22—C31—C32	−49.64 (15)	S1B—C14—S1A—C1A	79.4 (13)
C21—C22—C31—C32	140.55 (13)	C13—C14—S1B—C1B	−70.6 (7)
C23—C22—C31—C35	72.09 (14)	C15—C14—S1B—C1B	113.1 (7)
C21—C22—C31—C35	−97.72 (14)	S1A—C14—S1B—C1B	−57.5 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···N22ⁱ	0.83 (3)	2.09 (3)	2.8982 (18)	167 (2)
O8—H8B···O4ⁱⁱ	0.84 (3)	2.09 (3)	2.8989 (19)	164 (2)
N21—H21···O2ⁱⁱⁱ	0.884 (19)	1.985 (19)	2.8505 (15)	165.9 (17)
N31—H31A···O8^iv	0.908 (19)	1.965 (19)	2.8561 (18)	166.6 (17)
C23—H23···S1A^v	0.95	2.79	3.637 (3)	149
C31—H31···O1	1.00	2.35	2.7141 (14)	101
C31—H31···O3	1.00	2.35	2.7246 (15)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8A⋯N22ⁱ	0.83 (3)	2.09 (3)	2.8982 (18)	167 (2)
O8—H8B⋯O4ⁱⁱ	0.84 (3)	2.09 (3)	2.8989 (19)	164 (2)
N21—H21⋯O2ⁱⁱⁱ	0.884 (19)	1.985 (19)	2.8505 (15)	165.9 (17)
N31—H31A⋯O8^iv	0.908 (19)	1.965 (19)	2.8561 (18)	166.6 (17)
C23—H23⋯S1A ^v	0.95	2.79	3.637 (3)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

7 in total

Review 4. Calcium antagonists in hypertension.

Authors: F R Bühler; W Kiowski
Journal: J Hypertens Suppl Date: 1987-08

5. Syntheses, calcium channel agonist-antagonist modulation activities, and voltage-clamp studies of isopropyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-pyridinylpyridine-5-carboxylate racemates and enantiomers.

Authors: D Vo; W C Matowe; M Ramesh; N Iqbal; M W Wolowyk; S E Howlett; E E Knaus
Journal: J Med Chem Date: 1995-07-21 Impact factor: 7.446

6. Oxidation of 4-aryl- and 4-alkyl-substituted 2,6-dimethyl-3,5-bis(alkoxycarbonyl)-1,4-dihydropyridines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450.

Authors: R H Böcker; F P Guengerich
Journal: J Med Chem Date: 1986-09 Impact factor: 7.446

7. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20