Dimethyl 5,6,7-trimeth-oxy-2-methyl-1,2-dihydro-quinoline-2,4-dicarboxyl-ate.

In the title compound, C(17)H(21)NO(7), the dihydro-pyridine ring assumes a screw-boat conformation. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules, forming supra-molecular chains running along the b axis.

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 & Weissmann (1971 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H21NO7

M = 351.35

Orthorhombic,

a = 10.476 (2) Å

b = 16.552 (4) Å

c = 20.238 (4) Å

V = 3509.2 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.6 × 0.4 × 0.15 mm

Data collection

Nicolet P3 diffractometer

3447 measured reflections

3447 independent reflections

1839 reflections with I > 2σ(I)

3 standard reflections every 50 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.156

S = 1.07

3447 reflections

237 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.17 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004028/xu5153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004028/xu5153Isup2.hkl

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

C17H21NO7	F(000) = 1488
Mr = 351.35	Dx = 1.330 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 40 reflections
a = 10.476 (2) Å	θ = 10–12°
b = 16.552 (4) Å	µ = 0.10 mm−1
c = 20.238 (4) Å	T = 294 K
V = 3509.2 (13) Å3	Plates, colourless
Z = 8	0.6 × 0.4 × 0.15 mm

Nicolet P3 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.0°
graphite	h = 0→12
Wyckoff scan	k = 0→20
3447 measured reflections	l = 0→24
3447 independent reflections	3 standard reflections every 50 reflections
1839 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)] = 0.070	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0359P)2 + 3.112P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3447 reflections	Δρmax = 0.18 e Å−3
237 parameters	Δρmin = −0.17 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: 0.0031 (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 > 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	Uiso*/Ueq
O1	0.5908 (3)	1.03546 (16)	0.62717 (15)	0.0881 (10)
O2	0.6233 (3)	0.93649 (16)	0.55547 (13)	0.0713 (8)
O3	0.2547 (3)	0.7747 (2)	0.51994 (16)	0.1002 (11)
O4	0.1503 (3)	0.75844 (14)	0.61564 (14)	0.0745 (8)
O5	0.0584 (2)	0.91803 (14)	0.58046 (11)	0.0540 (6)
O6	−0.0366 (2)	1.05816 (15)	0.63970 (12)	0.0637 (7)
O7	0.1046 (3)	1.13852 (16)	0.72647 (13)	0.0736 (8)
N1	0.4420 (3)	0.9400 (2)	0.70665 (15)	0.0590 (9)
H21	0.485 (4)	0.973 (2)	0.733 (2)	0.091 (16)*
C1	0.5191 (3)	0.9018 (2)	0.65584 (19)	0.0525 (9)
C2	0.4333 (3)	0.8467 (2)	0.61660 (18)	0.0536 (9)
H2	0.4696	0.8031	0.5946	0.064*
C3	0.3086 (3)	0.85768 (19)	0.61218 (16)	0.0479 (8)
C4	0.2492 (3)	0.92839 (19)	0.64312 (15)	0.0445 (8)
C5	0.1281 (3)	0.9578 (2)	0.62794 (16)	0.0457 (8)
C6	0.0824 (3)	1.0285 (2)	0.65599 (17)	0.0489 (9)
C7	0.1567 (3)	1.0694 (2)	0.70186 (17)	0.0541 (9)
C8	0.2776 (3)	1.0412 (2)	0.71861 (17)	0.0566 (10)
H8	0.3272	1.0688	0.7493	0.068*
C9	0.3233 (3)	0.9712 (2)	0.68871 (16)	0.0489 (9)
C10	0.6265 (4)	0.8538 (2)	0.6884 (2)	0.0730 (12)
H10A	0.6801	0.8899	0.7132	0.109*
H10B	0.6763	0.8274	0.6550	0.109*
H10C	0.5907	0.8141	0.7176	0.109*
C11	0.5798 (3)	0.9663 (2)	0.61161 (19)	0.0528 (9)
C12	0.6849 (5)	0.9931 (3)	0.5108 (2)	0.1013 (16)
H12A	0.6974	0.9678	0.4686	0.152*
H12B	0.7660	1.0088	0.5287	0.152*
H12C	0.6319	1.0400	0.5055	0.152*
C13	0.2345 (4)	0.7940 (2)	0.5758 (2)	0.0613 (10)
C14	0.0782 (5)	0.6925 (3)	0.5864 (3)	0.118 (2)
H14A	0.0260	0.6676	0.6197	0.177*
H14B	0.1362	0.6532	0.5686	0.177*
H14C	0.0249	0.7130	0.5517	0.177*
C15	−0.0622 (3)	0.8868 (2)	0.6031 (2)	0.0755 (12)
H15A	−0.1022	0.8569	0.5682	0.113*
H15B	−0.1164	0.9308	0.6160	0.113*
H15C	−0.0483	0.8519	0.6403	0.113*
C16	−0.0349 (5)	1.1165 (3)	0.5882 (2)	0.0906 (15)
H16A	−0.1179	1.1406	0.5842	0.136*
H16B	−0.0124	1.0907	0.5474	0.136*
H16C	0.0268	1.1576	0.5984	0.136*
C17	0.1819 (4)	1.1883 (2)	0.7671 (2)	0.0896 (15)
H17A	0.1360	1.2367	0.7781	0.134*
H17B	0.2587	1.2022	0.7438	0.134*
H17C	0.2033	1.1597	0.8069	0.134*

	U11	U22	U33	U12	U13	U23
O1	0.111 (3)	0.0508 (17)	0.103 (2)	−0.0080 (17)	0.014 (2)	0.0001 (16)
O2	0.0779 (19)	0.0685 (17)	0.0676 (18)	−0.0126 (15)	0.0092 (15)	−0.0002 (15)
O3	0.101 (2)	0.115 (3)	0.085 (2)	−0.028 (2)	0.012 (2)	−0.047 (2)
O4	0.0813 (18)	0.0507 (15)	0.092 (2)	−0.0248 (15)	−0.0035 (17)	−0.0025 (15)
O5	0.0507 (14)	0.0598 (15)	0.0516 (14)	−0.0123 (12)	−0.0065 (12)	−0.0034 (12)
O6	0.0493 (15)	0.0704 (17)	0.0712 (18)	0.0042 (13)	0.0024 (13)	−0.0002 (14)
O7	0.0750 (19)	0.0670 (17)	0.0789 (19)	0.0009 (15)	0.0051 (15)	−0.0253 (15)
N1	0.0520 (19)	0.073 (2)	0.0524 (19)	−0.0034 (18)	−0.0093 (16)	−0.0077 (17)
C1	0.050 (2)	0.048 (2)	0.060 (2)	0.0010 (18)	−0.0078 (18)	0.0047 (18)
C2	0.056 (2)	0.0443 (19)	0.060 (2)	0.0016 (18)	−0.0018 (19)	0.0009 (17)
C3	0.055 (2)	0.0426 (19)	0.046 (2)	−0.0088 (17)	−0.0019 (17)	0.0038 (16)
C4	0.0478 (18)	0.0465 (18)	0.0391 (17)	−0.0091 (17)	0.0019 (16)	−0.0005 (16)
C5	0.0453 (19)	0.052 (2)	0.0395 (18)	−0.0142 (17)	−0.0014 (16)	−0.0009 (16)
C6	0.0425 (19)	0.053 (2)	0.051 (2)	−0.0064 (17)	0.0045 (17)	−0.0020 (17)
C7	0.055 (2)	0.052 (2)	0.055 (2)	−0.0057 (19)	0.0102 (19)	−0.0077 (18)
C8	0.058 (2)	0.063 (2)	0.049 (2)	−0.013 (2)	0.0029 (18)	−0.0144 (19)
C9	0.047 (2)	0.056 (2)	0.043 (2)	−0.0094 (18)	−0.0022 (17)	0.0025 (17)
C10	0.064 (2)	0.069 (3)	0.086 (3)	0.003 (2)	−0.017 (2)	0.020 (2)
C11	0.045 (2)	0.050 (2)	0.063 (2)	0.0026 (18)	−0.0061 (19)	0.0045 (19)
C12	0.104 (4)	0.115 (4)	0.085 (3)	−0.029 (3)	0.017 (3)	0.027 (3)
C13	0.060 (2)	0.054 (2)	0.070 (3)	−0.008 (2)	−0.001 (2)	−0.009 (2)
C14	0.106 (4)	0.072 (3)	0.176 (6)	−0.041 (3)	−0.005 (4)	−0.029 (3)
C15	0.050 (2)	0.075 (3)	0.102 (3)	−0.016 (2)	−0.006 (2)	−0.009 (2)
C16	0.094 (3)	0.072 (3)	0.106 (4)	0.006 (3)	−0.017 (3)	0.021 (3)
C17	0.104 (4)	0.073 (3)	0.092 (4)	−0.006 (3)	0.000 (3)	−0.038 (3)

O1—C11	1.193 (4)	C5—C6	1.386 (5)
O2—C11	1.320 (4)	C6—C7	1.387 (5)
O2—C12	1.453 (5)	C7—C8	1.391 (5)
O3—C13	1.194 (4)	C8—C9	1.393 (5)
O4—C13	1.332 (4)	C8—H8	0.9300
O4—C14	1.453 (5)	C10—H10A	0.9600
O5—C5	1.374 (4)	C10—H10B	0.9600
O5—C15	1.440 (4)	C10—H10C	0.9600
O6—C6	1.380 (4)	C12—H12A	0.9600
O6—C16	1.421 (5)	C12—H12B	0.9600
O7—C7	1.362 (4)	C12—H12C	0.9600
O7—C17	1.418 (4)	C14—H14A	0.9600
N1—C1	1.453 (4)	C14—H14B	0.9600
N1—C9	1.394 (4)	C14—H14C	0.9600
N1—H21	0.89 (4)	C15—H15A	0.9600
C1—C2	1.507 (5)	C15—H15B	0.9600
C1—C10	1.527 (5)	C15—H15C	0.9600
C1—C11	1.532 (5)	C16—H16A	0.9600
C2—C3	1.322 (4)	C16—H16B	0.9600
C2—H2	0.9300	C16—H16C	0.9600
C3—C4	1.466 (5)	C17—H17A	0.9600
C3—C13	1.502 (5)	C17—H17B	0.9600
C4—C5	1.393 (5)	C17—H17C	0.9600
C4—C9	1.399 (4)
C11—O2—C12	116.6 (3)	C1—C10—H10C	109.5
C13—O4—C14	115.5 (4)	H10A—C10—H10B	109.5
C5—O5—C15	114.5 (3)	H10A—C10—H10C	109.5
C6—O6—C16	113.9 (3)	H10B—C10—H10C	109.5
C7—O7—C17	118.1 (3)	O1—C11—O2	123.6 (4)
C1—N1—H21	114 (3)	O1—C11—C1	123.7 (4)
C9—N1—C1	118.2 (3)	O2—C11—C1	112.7 (3)
C9—N1—H21	112 (3)	O2—C12—H12A	109.5
N1—C1—C2	107.7 (3)	O2—C12—H12B	109.5
N1—C1—C10	109.3 (3)	O2—C12—H12C	109.5
N1—C1—C11	109.9 (3)	H12A—C12—H12B	109.5
C2—C1—C10	110.7 (3)	H12A—C12—H12C	109.5
C2—C1—C11	111.2 (3)	H12B—C12—H12C	109.5
C10—C1—C11	108.0 (3)	O3—C13—O4	124.9 (4)
C1—C2—H2	118.6	O3—C13—C3	124.1 (4)
C3—C2—C1	122.8 (3)	O4—C13—C3	110.9 (3)
C3—C2—H2	118.6	O4—C14—H14A	109.5
C2—C3—C4	120.1 (3)	O4—C14—H14B	109.5
C2—C3—C13	116.6 (3)	O4—C14—H14C	109.5
C4—C3—C13	123.4 (3)	H14A—C14—H14B	109.5
C5—C4—C3	124.9 (3)	H14A—C14—H14C	109.5
C5—C4—C9	118.3 (3)	H14B—C14—H14C	109.5
C9—C4—C3	116.7 (3)	O5—C15—H15A	109.5
O5—C5—C4	118.1 (3)	O5—C15—H15B	109.5
O5—C5—C6	120.5 (3)	O5—C15—H15C	109.5
C6—C5—C4	121.3 (3)	H15A—C15—H15B	109.5
O6—C6—C5	120.9 (3)	H15A—C15—H15C	109.5
O6—C6—C7	119.6 (3)	H15B—C15—H15C	109.5
C5—C6—C7	119.5 (3)	O6—C16—H16A	109.5
O7—C7—C6	115.4 (3)	O6—C16—H16B	109.5
O7—C7—C8	123.9 (3)	O6—C16—H16C	109.5
C6—C7—C8	120.7 (3)	H16A—C16—H16B	109.5
C7—C8—C9	119.1 (3)	H16A—C16—H16C	109.5
C7—C8—H8	120.5	H16B—C16—H16C	109.5
C9—C8—H8	120.5	O7—C17—H17A	109.5
N1—C9—C4	118.7 (3)	O7—C17—H17B	109.5
C8—C9—N1	120.1 (3)	O7—C17—H17C	109.5
C8—C9—C4	121.1 (3)	H17A—C17—H17B	109.5
C1—C10—H10A	109.5	H17A—C17—H17C	109.5
C1—C10—H10B	109.5	H17B—C17—H17C	109.5
C12—O2—C11—O1	−1.3 (6)	C2—C3—C4—C9	−14.3 (5)
C12—O2—C11—C1	−178.8 (3)	C13—C3—C4—C5	−19.0 (5)
C14—O4—C13—O3	−1.0 (6)	C13—C3—C4—C9	164.4 (3)
C14—O4—C13—C3	−176.6 (3)	C2—C3—C13—O3	−57.5 (6)
C15—O5—C5—C4	120.6 (3)	C2—C3—C13—O4	118.1 (4)
C15—O5—C5—C6	−64.2 (4)	C4—C3—C13—O3	123.8 (5)
C16—O6—C6—C5	−94.5 (4)	C4—C3—C13—O4	−60.6 (4)
C16—O6—C6—C7	86.5 (4)	C3—C4—C5—O5	−0.1 (5)
C17—O7—C7—C6	−172.3 (3)	C3—C4—C5—C6	−175.2 (3)
C17—O7—C7—C8	5.6 (5)	C9—C4—C5—O5	176.5 (3)
C9—N1—C1—C2	−45.4 (4)	C9—C4—C5—C6	1.3 (5)
C9—N1—C1—C10	−165.7 (3)	C3—C4—C9—N1	−6.3 (4)
C9—N1—C1—C11	76.0 (4)	C3—C4—C9—C8	177.2 (3)
C1—N1—C9—C8	−145.0 (3)	C5—C4—C9—N1	176.8 (3)
C1—N1—C9—C4	38.5 (5)	C5—C4—C9—C8	0.3 (5)
N1—C1—C2—C3	24.7 (5)	O5—C5—C6—O6	3.6 (5)
C10—C1—C2—C3	144.2 (4)	O5—C5—C6—C7	−177.4 (3)
C11—C1—C2—C3	−95.8 (4)	C4—C5—C6—O6	178.7 (3)
N1—C1—C11—O1	18.8 (5)	C4—C5—C6—C7	−2.3 (5)
N1—C1—C11—O2	−163.7 (3)	C5—C6—C7—O7	179.6 (3)
C2—C1—C11—O1	138.0 (4)	C5—C6—C7—C8	1.7 (5)
C2—C1—C11—O2	−44.5 (4)	O6—C6—C7—O7	−1.4 (5)
C10—C1—C11—O1	−100.4 (4)	O6—C6—C7—C8	−179.3 (3)
C10—C1—C11—O2	77.1 (4)	O7—C7—C8—C9	−177.8 (3)
C1—C2—C3—C4	3.5 (5)	C6—C7—C8—C9	0.0 (5)
C1—C2—C3—C13	−175.2 (3)	C7—C8—C9—N1	−177.4 (3)
C2—C3—C4—C5	162.3 (3)	C7—C8—C9—C4	−1.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1i	0.96	2.51	3.251 (6)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1i	0.96	2.51	3.251 (6)	134

Symmetry code: (i) .