Literature DB >> 21522421

Dimethyl 2-methyl-1,2-dihydro-quinoline-2,4-dicarboxyl-ate.

Zeynep Gültekin, Wolfgang Frey, Barış Tercan, Tuncer Hökelek.

Abstract

In the crystal of the title compound, C(14)H(15)NO(4), pairs of inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric R(2) (2)(10) dimers. These dimers are further connected via inter-molecular C-H⋯O hydrogen bonds, forming a three-dimensional network. The heterocyclic ring adopts a twisted conformation.

Entities: CellLine Chemical Disease Gene

Year: 2011 PMID： 21522421 PMCID： PMC3052156 DOI： 10.1107/S1600536811005605

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

Related literature

For the preparation of 1,2-dihydroquinoline, see: Edwards et al. (1998 ▶); Yan et al. (2004 ▶); Petasis & Butkevich (2009 ▶); Johnson et al. (1989 ▶); Gültekin et al. (2010 ▶); Waldmann et al. (2008 ▶). For the biological activity of dihydroquinolines, see: Elmore et al. (2001 ▶); Dillard et al. (1973 ▶); Muren & Weissman (1971 ▶). For the preparation of quinolines, see: Dauphinee & Forrest (1978 ▶); Yan et al. (2004 ▶); Tom & Ruel (2001 ▶); Tokuyama et al. (2001 ▶); Sarma & Prajapati (2008 ▶); Martinez et al. (2008 ▶); Huang et al. (2009 ▶); Katritzky et al. (1996 ▶). For the biological activity of quinolines, see: Hamann et al. (1998 ▶); He et al. (2003 ▶); LaMontagne et al. (1989 ▶). For hydorgen-bond motifs, see: Bernstein et al. (1995 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For the melting point, see: Rueping & Gültekin (2009 ▶).

Experimental

Crystal data

C14H15NO4 M = 261.27 Monoclinic, a = 7.9917 (12) Å b = 8.8886 (11) Å c = 18.9855 (18) Å β = 99.194 (9)° V = 1331.3 (3) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 294 K 0.6 × 0.6 × 0.5 mm

Data collection

Nicolet P3 diffractometer 4144 measured reflections 3890 independent reflections 3097 reflections with I > 2σ(I) R int = 0.053 3 standard reflections every 50 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.159 S = 1.05 3890 reflections 180 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.24 e Å−3 Δρmin = −0.18 e Å−3 Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005605/bv2176sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005605/bv2176Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₅NO₄	F(000) = 552
M_r = 261.27	D_x = 1.304 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 49 reflections
a = 7.9917 (12) Å	θ = 17–18°
b = 8.8886 (11) Å	µ = 0.10 mm⁻¹
c = 18.9855 (18) Å	T = 294 K
β = 99.194 (9)°	Block, colourless
V = 1331.3 (3) Å³	0.6 × 0.6 × 0.5 mm
Z = 4

Nicolet P3 diffractometer	R_int = 0.053
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 2.2°
graphite	h = 0→11
Wyckoff–Scan scans	k = 0→12
4144 measured reflections	l = −26→26
3890 independent reflections	3 standard reflections every 50 reflections
3097 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.159	w = 1/[σ²(F_o²) + (0.0757P)² + 0.2951P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3890 reflections	Δρ_max = 0.24 e Å⁻³
180 parameters	Δρ_min = −0.18 e Å⁻³
0 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: 0.076 (5)

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 > 2sigma(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	U_iso*/U_eq
O1	0.16885 (15)	0.61815 (14)	0.96958 (6)	0.0632 (3)
O2	0.15641 (17)	0.84306 (14)	0.91740 (6)	0.0671 (4)
O3	−0.04420 (19)	0.60887 (14)	0.63398 (6)	0.0688 (4)
O4	0.00900 (15)	0.83447 (13)	0.68455 (5)	0.0538 (3)
N1	−0.12790 (17)	0.52602 (16)	0.88407 (7)	0.0527 (3)
H1	−0.137 (3)	0.491 (3)	0.9282 (12)	0.080 (6)*
C1	−0.08128 (18)	0.68333 (17)	0.88397 (7)	0.0447 (3)
C2	−0.07661 (18)	0.73116 (16)	0.80816 (7)	0.0441 (3)
H2	−0.1036	0.8299	0.7946	0.053*
C3	−0.03445 (17)	0.63452 (15)	0.76014 (7)	0.0411 (3)
C4	−0.00240 (17)	0.47523 (15)	0.77879 (7)	0.0439 (3)
C5	0.0730 (2)	0.37209 (18)	0.73815 (9)	0.0551 (4)
H5	0.1104	0.4042	0.6967	0.066*
C6	0.0929 (2)	0.22295 (19)	0.75842 (11)	0.0675 (5)
H6	0.1440	0.1557	0.7309	0.081*
C7	0.0370 (3)	0.17430 (19)	0.81939 (12)	0.0723 (5)
H7	0.0479	0.0734	0.8323	0.087*
C8	−0.0351 (2)	0.27357 (19)	0.86154 (10)	0.0630 (4)
H8	−0.0718	0.2393	0.9028	0.076*
C9	−0.05340 (17)	0.42528 (16)	0.84272 (8)	0.0468 (3)
C10	−0.2084 (2)	0.7764 (2)	0.91791 (10)	0.0689 (5)
H10A	−0.2112	0.7408	0.9654	0.103*
H10B	−0.3191	0.7667	0.8899	0.103*
H10C	−0.1749	0.8802	0.9197	0.103*
C11	0.09548 (18)	0.70811 (16)	0.92869 (6)	0.0432 (3)
C12	0.3182 (3)	0.8827 (3)	0.95860 (10)	0.0782 (6)
H12A	0.3519	0.9801	0.9441	0.117*
H12B	0.4015	0.8094	0.9507	0.117*
H12C	0.3087	0.8848	1.0084	0.117*
C13	−0.02495 (18)	0.68793 (17)	0.68624 (7)	0.0455 (3)
C14	0.0372 (3)	0.8942 (2)	0.61686 (9)	0.0639 (4)
H14A	0.0545	1.0009	0.6209	0.096*
H14B	−0.0598	0.8739	0.5813	0.096*
H14C	0.1355	0.8477	0.6032	0.096*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0643 (7)	0.0639 (7)	0.0556 (6)	−0.0034 (5)	−0.0082 (5)	0.0187 (5)
O2	0.0860 (9)	0.0569 (7)	0.0495 (6)	−0.0208 (6)	−0.0163 (6)	0.0115 (5)
O3	0.1070 (10)	0.0603 (7)	0.0347 (5)	0.0046 (7)	−0.0018 (6)	−0.0064 (5)
O4	0.0706 (7)	0.0516 (6)	0.0369 (5)	−0.0038 (5)	0.0014 (4)	0.0041 (4)
N1	0.0563 (7)	0.0561 (7)	0.0457 (6)	−0.0088 (6)	0.0077 (5)	0.0054 (5)
C1	0.0484 (7)	0.0491 (7)	0.0360 (6)	0.0029 (6)	0.0048 (5)	0.0012 (5)
C2	0.0518 (7)	0.0421 (6)	0.0356 (6)	0.0049 (5)	−0.0014 (5)	0.0021 (5)
C3	0.0438 (6)	0.0423 (6)	0.0340 (5)	0.0002 (5)	−0.0033 (5)	0.0004 (5)
C4	0.0449 (6)	0.0411 (6)	0.0415 (6)	−0.0011 (5)	−0.0056 (5)	−0.0011 (5)
C5	0.0600 (9)	0.0502 (8)	0.0507 (8)	0.0060 (7)	−0.0046 (6)	−0.0072 (6)
C6	0.0735 (11)	0.0476 (8)	0.0732 (11)	0.0094 (8)	−0.0133 (9)	−0.0119 (8)
C7	0.0816 (12)	0.0385 (8)	0.0861 (13)	−0.0058 (8)	−0.0198 (10)	0.0041 (8)
C8	0.0688 (10)	0.0475 (8)	0.0666 (10)	−0.0150 (7)	−0.0081 (8)	0.0117 (7)
C9	0.0450 (7)	0.0444 (7)	0.0470 (7)	−0.0092 (5)	−0.0054 (5)	0.0037 (5)
C10	0.0674 (10)	0.0854 (13)	0.0559 (9)	0.0197 (9)	0.0157 (8)	−0.0024 (9)
C11	0.0522 (7)	0.0478 (7)	0.0296 (5)	−0.0014 (5)	0.0063 (5)	0.0015 (5)
C12	0.0917 (13)	0.0891 (14)	0.0472 (9)	−0.0413 (12)	−0.0086 (8)	0.0045 (9)
C13	0.0498 (7)	0.0487 (7)	0.0343 (6)	0.0046 (6)	−0.0042 (5)	−0.0008 (5)
C14	0.0774 (11)	0.0698 (11)	0.0430 (8)	−0.0016 (8)	0.0053 (7)	0.0141 (7)

O1—C11	1.2001 (17)	C5—C6	1.382 (2)
O2—C11	1.3249 (18)	C5—H5	0.9300
O2—C12	1.443 (2)	C6—C7	1.376 (3)
O3—C13	1.2055 (17)	C6—H6	0.9300
O4—C13	1.3319 (19)	C7—C8	1.377 (3)
O4—C14	1.4410 (18)	C7—H7	0.9300
N1—C1	1.447 (2)	C8—C9	1.397 (2)
N1—C9	1.386 (2)	C8—H8	0.9300
N1—H1	0.91 (2)	C10—H10A	0.9600
C1—C2	1.5070 (18)	C10—H10B	0.9600
C1—C10	1.530 (2)	C10—H10C	0.9600
C1—C11	1.5432 (19)	C12—H12A	0.9600
C2—C3	1.3344 (19)	C12—H12B	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C3—C4	1.4720 (19)	C14—H14A	0.9600
C3—C13	1.4944 (18)	C14—H14B	0.9600
C4—C5	1.395 (2)	C14—H14C	0.9600
C4—C9	1.412 (2)

C11—O2—C12	116.97 (13)	C7—C8—H8	119.8
C13—O4—C14	116.33 (13)	C9—C8—H8	119.8
C1—N1—H1	112.9 (15)	N1—C9—C4	119.52 (13)
C9—N1—C1	119.30 (12)	N1—C9—C8	121.05 (15)
C9—N1—H1	114.2 (14)	C8—C9—C4	119.37 (15)
N1—C1—C2	108.63 (12)	C1—C10—H10A	109.5
N1—C1—C10	109.48 (14)	C1—C10—H10B	109.5
N1—C1—C11	110.51 (12)	C1—C10—H10C	109.5
C2—C1—C10	111.66 (13)	H10A—C10—H10B	109.5
C2—C1—C11	108.97 (11)	H10A—C10—H10C	109.5
C10—C1—C11	107.59 (13)	H10B—C10—H10C	109.5
C1—C2—H2	119.4	O1—C11—O2	123.62 (14)
C3—C2—C1	121.23 (12)	O1—C11—C1	124.78 (13)
C3—C2—H2	119.4	O2—C11—C1	111.59 (12)
C2—C3—C4	120.53 (12)	O2—C12—H12A	109.5
C2—C3—C13	119.55 (12)	O2—C12—H12B	109.5
C4—C3—C13	119.90 (12)	O2—C12—H12C	109.5
C5—C4—C3	124.94 (13)	H12A—C12—H12B	109.5
C5—C4—C9	118.56 (14)	H12A—C12—H12C	109.5
C9—C4—C3	116.50 (13)	H12B—C12—H12C	109.5
C4—C5—H5	119.4	O3—C13—O4	123.36 (14)
C6—C5—C4	121.12 (17)	O3—C13—C3	124.65 (14)
C6—C5—H5	119.4	O4—C13—C3	111.99 (11)
C5—C6—H6	120.1	O4—C14—H14A	109.5
C7—C6—C5	119.82 (18)	O4—C14—H14B	109.5
C7—C6—H6	120.1	O4—C14—H14C	109.5
C6—C7—C8	120.64 (16)	H14A—C14—H14B	109.5
C6—C7—H7	119.7	H14A—C14—H14C	109.5
C8—C7—H7	119.7	H14B—C14—H14C	109.5
C7—C8—C9	120.43 (18)

C12—O2—C11—O1	−1.7 (2)	C2—C3—C4—C5	−167.06 (14)
C12—O2—C11—C1	177.32 (15)	C2—C3—C4—C9	13.20 (19)
C14—O4—C13—O3	−5.3 (2)	C13—C3—C4—C5	14.8 (2)
C14—O4—C13—C3	174.17 (13)	C13—C3—C4—C9	−164.94 (12)
C9—N1—C1—C2	44.10 (17)	C2—C3—C13—O3	−154.18 (16)
C9—N1—C1—C10	166.27 (14)	C2—C3—C13—O4	26.33 (18)
C9—N1—C1—C11	−75.40 (16)	C4—C3—C13—O3	24.0 (2)
C1—N1—C9—C4	−30.23 (19)	C4—C3—C13—O4	−155.51 (12)
C1—N1—C9—C8	152.77 (14)	C3—C4—C5—C6	−177.69 (14)
N1—C1—C2—C3	−31.14 (18)	C9—C4—C5—C6	2.0 (2)
C10—C1—C2—C3	−151.98 (15)	C3—C4—C9—N1	−0.52 (18)
C11—C1—C2—C3	89.32 (16)	C3—C4—C9—C8	176.53 (13)
N1—C1—C11—O1	−14.36 (19)	C5—C4—C9—N1	179.73 (13)
N1—C1—C11—O2	166.68 (12)	C5—C4—C9—C8	−3.2 (2)
C2—C1—C11—O1	−133.65 (15)	C4—C5—C6—C7	0.4 (3)
C2—C1—C11—O2	47.38 (16)	C5—C6—C7—C8	−1.6 (3)
C10—C1—C11—O1	105.13 (18)	C6—C7—C8—C9	0.4 (3)
C10—C1—C11—O2	−73.84 (16)	C7—C8—C9—N1	179.06 (15)
C1—C2—C3—C4	4.2 (2)	C7—C8—C9—C4	2.1 (2)
C1—C2—C3—C13	−177.68 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.91 (2)	2.22 (2)	3.1241 (18)	174 (2)
C12—H12A···O3ⁱⁱ	0.96	2.57	3.377 (3)	142
C12—H12C···O3ⁱⁱⁱ	0.96	2.49	3.336 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.91 (2)	2.22 (2)	3.1241 (18)	174 (2)
C12—H12A⋯O3ⁱⁱ	0.96	2.57	3.377 (3)	142
C12—H12C⋯O3ⁱⁱⁱ	0.96	2.49	3.336 (2)	148

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

14 in total

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Authors: S W Elmore; M J Coghlan; D D Anderson; J K Pratt; B E Green; A X Wang; M A Stashko; C W Lin; C M Tyree; J N Miner; P B Jacobson; D M Wilcox; B C Lane
Journal: J Med Chem Date: 2001-12-06 Impact factor: 7.446

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Authors: M P LaMontagne; P Blumbergs; D C Smith
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3. Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2-dihydropyridono[5,6-g]quinolines.

Authors: L G Hamann; R I Higuchi; L Zhi; J P Edwards; X N Wang; K B Marschke; J W Kong; L J Farmer; T K Jones
Journal: J Med Chem Date: 1998-02-12 Impact factor: 7.446

4. Depressant 1,2-dihydroquinolines and related derivatives.

Authors: J F Muren; A Weissman
Journal: J Med Chem Date: 1971-01 Impact factor: 7.446

5. Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern--synthesis and biological activity studies of 11H-indolo[3.2-c]quinoline derivatives.

Authors: Ling He; He-Xi Chang; Ting-Chao Chou; Niramol Savaraj; C C Cheng
Journal: Eur J Med Chem Date: 2003-01 Impact factor: 6.514

6. 2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 12. 1,2-Dihydroquinolylmethyl analogues with high activity and specificity for bacterial dihydrofolate reductase.

Authors: J V Johnson; B S Rauchman; D P Baccanari; B Roth
Journal: J Med Chem Date: 1989-08 Impact factor: 7.446

7. A simple and convenient copper-catalyzed tandem synthesis of quinoline-2-carboxylates at room temperature.

Authors: He Huang; Hualiang Jiang; Kaixian Chen; Hong Liu
Journal: J Org Chem Date: 2009-08-07 Impact factor: 4.354

8. Synthesis of 2H-chromenes and 1,2-dihydroquinolines from aryl aldehydes, amines, and alkenylboron compounds.

Authors: Nicos A Petasis; Alexey Butkevich
Journal: J Organomet Chem Date: 2009-05-01 Impact factor: 2.369

9. An investigation of the reaction of 2-aminobenzaldehyde derivatives with conjugated nitro-olefins: an easy and efficient synthesis of 3-nitro-1,2-dihydroquinolines and 3-nitroquinolines.

Authors: Ming-Chung Yan; Zhijay Tu; Chunchi Lin; Shengkai Ko; Jianming Hsu; Ching-Fa Yao
Journal: J Org Chem Date: 2004-03-05 Impact factor: 4.354