(±)-Ethyl 6,7-dimeth­oxy-1-(1H-pyrrol-2-yl)-1,2,3,4-tetra­hydroisoquinoline-2-car­boxyl­ate

Nikolova, R.P.; Kolev, T.; Statkova-Abeghe, S.M.; Shivachev, B.L.

doi:10.1107/S1600536808026020

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1796

doi:10.1107/S1600536808026020

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(±)-Ethyl 6,7-dimethoxy-1-(1H-pyrrol-2-yl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Rosica Petrova Nikolova,^a Tsonko Kolev,^b Stela M. Statkova-Abeghe ^c and Boris Lubomirov Shivachev ^d ^*

^aDepartment of Advanced Materials Science and Engineering, Faculty of Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube 755-8611, Japan, ^bBulgarian Academy of Sciences, Institute of Organic Chemistry, Acad G. Bonchev Str. build. 9, 1113 Sofia, Bulgaria, ^cPlovdiv University, Department of Organic Chemistry, 4000 Plovdiv, Bulgaria, and ^dDepartment of Structural Biology, University of Pittsburgh School of Medicine, 3501 5th Ave., Pittsburgh 15260, USA
^*Correspondence e-mail: blc53@pitt.edu

(Received 29 July 2008; accepted 12 August 2008; online 20 August 2008)

In the title compound, C₁₈H₂₂N₂O₄, the dihedral angle between the pyrrolyl and quinolinyl fragments is 68.97 (2)°. Two non-classical intramolecular C—H⋯O hydrogen bonds stabilize the molecular geometry. In the crystal structure, molecules form infinite chains via moderate intermolecular N—H⋯O(CH₃) hydrogen bonds.

Related literature

For related crystal structures, see: Kolev et al. (2007 ); Petrova et al. (2007 ); Petrova et al. (2005 ); Rajnikant et al. (2002 ); Shishkina et al. (2005 ); Venkov et al. (2004 ); Vincente et al. (2005 ).

Experimental

Crystal data

C₁₈H₂₂N₂O₄
M_r = 330.38
Monoclinic, P 2₁ /c
a = 8.403 (3) Å
b = 17.046 (3) Å
c = 11.6486 (13) Å
β = 95.260 (13)°
V = 1661.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 290 (2) K
0.32 × 0.32 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
6852 measured reflections
3263 independent reflections
1828 reflections with I > 2σ(I)
R_int = 0.110
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.156
S = 1.07
3263 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.21 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
N3—H3⋯O1ⁱ	0.86	2.49	3.225 (4)	145
N3—H3⋯O2ⁱ	0.86	2.38	3.018 (4)	132
C7—H7⋯O4	0.98	2.34	2.784 (4)	107
C8—H8B⋯O3	0.97	2.29	2.653 (4)	101
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026020/pv2093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026020/pv2093Isup2.hkl

checkCIF report

Comment top

As part of our research program on tetrahydroisoquinolines (Kolev et al., 2007; Petrova et al., 2007; Petrova et al., 2005) the crystal structure of the title compound,(I), has been solved. The molecule possesses regular geometry with two nearly planar ring systems. The r.m.s. deviation of pyrrolyl and quinolin-2(1H)-fragments is 0.161 (7) Å and 0.002 (2) Å, respectively, and the dihedral angle between their mean planes is 68.97 (2)°. The geometrical parameters of both rings are comparable to those observed in other quinoline derivatives (Rajnikant et al., 2002; Vincente et al., 2005; Shishkina et al., 2005). Two non-classsical intramolecular hydrogen bonds (C7—H7···O4 and C8—H8···O3) stabilize the molecular geometry. Only the methoxy O atoms are realised as hydrogen bond acceptors and together with the only possible donor form a bifurcated hydrogen bond of the N—H···(O,O) type. Thus neighboring molecules are oriented head-to-tail and connected to form infinite chains along the b-axis (Fig. 2).

Related literature top

For related crystal structures, see: Kolev et al. (2007); Petrova et al. (2007); Petrova et al. (2005); Rajnikant et al. (2002); Shishkina et al. (2005); Venkov et al. (2004); Vincente et al. (2005).

Experimental top

The title compound has been obtained following the procedure described by Venkov et al., 2004. Colorless crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation from ethanol/water (2:1) solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 (Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the structure and the atom-numbering scheme of (I) showing 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of the molecular packing in (I). Hydrogen bonds are represented by dotted lines. H atoms not involved in hydrogen bonding interactions have been omitted. [Symmetry code: (i) -x, -1/2 + y, 1/2 - z].

(±)-Ethyl 6,7-dimethoxy-1-(1H-pyrrol-2-yl)-1,2,3,4-tetrahydroisoquinoline- 2-carboxylate top

Crystal data top

C₁₈H₂₂N₂O₄	F(000) = 704
M_r = 330.38	D_x = 1.321 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 22 reflections
a = 8.403 (3) Å	θ = 18.3–18.8°
b = 17.046 (3) Å	µ = 0.09 mm⁻¹
c = 11.6486 (13) Å	T = 290 K
β = 95.260 (13)°	Prism, colorless
V = 1661.5 (7) Å³	0.32 × 0.32 × 0.30 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.110
Radiation source: fine-focus sealed tube	θ_max = 26.0°, θ_min = 2.1°
Graphite monochromator	h = 0→10
Nonprofiled ω/2θ scans	k = −20→20
6852 measured reflections	l = −14→14
3263 independent reflections	3 standard reflections every 120 min
1828 reflections with I > 2σ(I)	intensity decay: −1%

Refinement top

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)] = 0.065	H-atom parameters constrained
wR(F²) = 0.156	w = 1/[σ²(F_o²) + (0.0293P)² + 2.0348P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3263 reflections	Δρ_max = 0.21 e Å⁻³
218 parameters	Δρ_min = −0.20 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: 0.0075 (10)

Crystal data top

C₁₈H₂₂N₂O₄	V = 1661.5 (7) Å³
M_r = 330.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.403 (3) Å	µ = 0.09 mm⁻¹
b = 17.046 (3) Å	T = 290 K
c = 11.6486 (13) Å	0.32 × 0.32 × 0.30 mm
β = 95.260 (13)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.110
6852 measured reflections	3 standard reflections every 120 min
3263 independent reflections	intensity decay: −1%
1828 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.07	Δρ_max = 0.21 e Å⁻³
3263 reflections	Δρ_min = −0.20 e Å⁻³
218 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	0.2084 (3)	0.63581 (14)	0.3413 (2)	0.0474 (7)
O2	0.3254 (3)	0.65266 (14)	0.1467 (2)	0.0443 (7)
O3	0.2237 (3)	0.20530 (14)	0.1157 (2)	0.0476 (7)
O4	0.2206 (3)	0.23765 (16)	0.3033 (2)	0.0573 (8)
N1	0.0630 (3)	0.30217 (16)	0.1633 (2)	0.0336 (7)
C2	0.2399 (4)	0.5223 (2)	0.0832 (3)	0.0339 (8)
H2	0.2815	0.5290	0.0126	0.041*
C19	−0.1547 (4)	0.37433 (19)	0.2412 (3)	0.0339 (8)
C6	0.1037 (4)	0.44139 (19)	0.2113 (3)	0.0329 (8)
C3	0.2542 (4)	0.58174 (19)	0.1623 (3)	0.0337 (8)
C13	−0.2492 (4)	0.4391 (2)	0.2366 (3)	0.0415 (9)
H13	−0.2154	0.4906	0.2277	0.050*
C7	0.0237 (4)	0.36515 (18)	0.2422 (3)	0.0347 (8)
H7	0.0659	0.3503	0.3204	0.042*
C9	0.1515 (4)	0.3882 (2)	0.0146 (3)	0.0408 (9)
H9A	0.2564	0.3657	0.0085	0.049*
H9B	0.1157	0.4115	−0.0593	0.049*
C5	0.1184 (4)	0.5026 (2)	0.2922 (3)	0.0352 (8)
H5	0.0780	0.4956	0.3632	0.042*
N3	−0.2512 (3)	0.31109 (17)	0.2555 (2)	0.0418 (8)
H3	−0.2197	0.2631	0.2616	0.050*
C10	0.1731 (4)	0.2482 (2)	0.2028 (3)	0.0395 (9)
C4	0.1907 (4)	0.5724 (2)	0.2694 (3)	0.0349 (8)
C18	0.4219 (5)	0.6587 (2)	0.0526 (3)	0.0555 (11)
H18A	0.4648	0.7109	0.0499	0.083*
H18B	0.3580	0.6479	−0.0182	0.083*
H18C	0.5080	0.6216	0.0626	0.083*
C1	0.1642 (4)	0.45151 (19)	0.1057 (3)	0.0323 (8)
C15	−0.4056 (5)	0.3361 (2)	0.2588 (3)	0.0498 (10)
H15	−0.4936	0.3042	0.2672	0.060*
C8	0.0366 (4)	0.3237 (2)	0.0414 (3)	0.0356 (8)
H8A	−0.0725	0.3415	0.0240	0.043*
H8B	0.0529	0.2782	−0.0061	0.043*
C17	0.1649 (5)	0.6268 (2)	0.4555 (3)	0.0527 (11)
H17A	0.1816	0.6754	0.4965	0.079*
H17B	0.2294	0.5865	0.4941	0.079*
H17C	0.0543	0.6123	0.4532	0.079*
C14	−0.4078 (5)	0.4148 (2)	0.2476 (3)	0.0491 (10)
H14	−0.4971	0.4471	0.2471	0.059*
C11	0.3387 (6)	0.1452 (3)	0.1464 (4)	0.0675 (14)
H11A	0.2972	0.1094	0.2010	0.081*
H11B	0.4361	0.1685	0.1824	0.081*
C12	0.3725 (6)	0.1029 (3)	0.0433 (4)	0.0812 (16)
H12A	0.4508	0.0630	0.0633	0.122*
H12B	0.4129	0.1387	−0.0106	0.122*
H12C	0.2761	0.0790	0.0090	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0666 (18)	0.0391 (15)	0.0374 (14)	−0.0089 (13)	0.0099 (13)	−0.0089 (12)
O2	0.0514 (15)	0.0414 (15)	0.0412 (14)	−0.0117 (12)	0.0110 (12)	−0.0012 (12)
O3	0.0551 (17)	0.0418 (15)	0.0455 (15)	0.0201 (13)	0.0028 (13)	−0.0023 (13)
O4	0.073 (2)	0.0578 (18)	0.0403 (16)	0.0254 (15)	0.0029 (14)	0.0079 (14)
N1	0.0403 (17)	0.0308 (16)	0.0298 (14)	0.0073 (14)	0.0035 (13)	0.0008 (13)
C2	0.0360 (19)	0.039 (2)	0.0275 (17)	0.0023 (16)	0.0060 (15)	0.0038 (15)
C19	0.043 (2)	0.0306 (19)	0.0297 (18)	−0.0011 (16)	0.0094 (16)	0.0005 (15)
C6	0.0326 (19)	0.0323 (19)	0.0339 (18)	0.0051 (15)	0.0040 (16)	−0.0011 (15)
C3	0.0330 (19)	0.0326 (19)	0.0351 (19)	−0.0019 (15)	0.0009 (16)	0.0030 (16)
C13	0.046 (2)	0.037 (2)	0.043 (2)	0.0064 (18)	0.0088 (18)	0.0034 (17)
C7	0.044 (2)	0.0297 (18)	0.0317 (18)	0.0025 (16)	0.0092 (16)	0.0011 (15)
C9	0.047 (2)	0.042 (2)	0.0335 (19)	0.0006 (18)	0.0074 (18)	−0.0034 (17)
C5	0.037 (2)	0.041 (2)	0.0289 (17)	0.0009 (17)	0.0065 (15)	0.0007 (17)
N3	0.0453 (19)	0.0350 (17)	0.0460 (18)	−0.0009 (15)	0.0084 (15)	0.0054 (15)
C10	0.043 (2)	0.037 (2)	0.039 (2)	0.0001 (18)	0.0094 (18)	0.0029 (17)
C4	0.041 (2)	0.0339 (19)	0.0297 (18)	0.0008 (16)	0.0014 (16)	−0.0043 (16)
C18	0.053 (3)	0.064 (3)	0.052 (2)	−0.016 (2)	0.016 (2)	0.000 (2)
C1	0.0322 (19)	0.0352 (19)	0.0299 (17)	0.0062 (15)	0.0043 (15)	0.0019 (15)
C15	0.041 (2)	0.060 (3)	0.050 (2)	−0.009 (2)	0.0124 (19)	−0.001 (2)
C8	0.041 (2)	0.0345 (19)	0.0306 (18)	0.0032 (16)	−0.0010 (15)	−0.0055 (16)
C17	0.067 (3)	0.054 (3)	0.038 (2)	−0.003 (2)	0.009 (2)	−0.011 (2)
C14	0.044 (2)	0.057 (3)	0.047 (2)	0.013 (2)	0.009 (2)	0.000 (2)
C11	0.077 (3)	0.052 (3)	0.073 (3)	0.030 (2)	0.006 (3)	−0.004 (2)
C12	0.083 (4)	0.076 (3)	0.084 (4)	0.035 (3)	0.004 (3)	−0.023 (3)

Geometric parameters (Å, º) top

O1—C4	1.367 (4)	C9—C8	1.515 (5)
O1—C17	1.420 (4)	C9—H9A	0.9700
O2—C3	1.369 (4)	C9—H9B	0.9700
O2—C18	1.426 (4)	C5—C4	1.374 (5)
O3—C10	1.350 (4)	C5—H5	0.9300
O3—C11	1.431 (5)	N3—C15	1.369 (5)
O4—C10	1.216 (4)	N3—H3	0.8600
N1—C10	1.355 (4)	C18—H18A	0.9600
N1—C8	1.464 (4)	C18—H18B	0.9600
N1—C7	1.470 (4)	C18—H18C	0.9600
C2—C3	1.367 (5)	C15—C14	1.349 (5)
C2—C1	1.399 (4)	C15—H15	0.9300
C2—H2	0.9300	C8—H8A	0.9700
C19—C13	1.359 (5)	C8—H8B	0.9700
C19—N3	1.368 (4)	C17—H17A	0.9600
C19—C7	1.506 (5)	C17—H17B	0.9600
C6—C1	1.385 (4)	C17—H17C	0.9600
C6—C5	1.403 (4)	C14—H14	0.9300
C6—C7	1.521 (4)	C11—C12	1.451 (6)
C3—C4	1.410 (4)	C11—H11A	0.9700
C13—C14	1.413 (5)	C11—H11B	0.9700
C13—H13	0.9300	C12—H12A	0.9600
C7—H7	0.9800	C12—H12B	0.9600
C9—C1	1.510 (4)	C12—H12C	0.9600

C4—O1—C17	117.8 (3)	O1—C4—C5	126.3 (3)
C3—O2—C18	116.9 (3)	O1—C4—C3	115.1 (3)
C10—O3—C11	116.9 (3)	C5—C4—C3	118.6 (3)
C10—N1—C8	122.5 (3)	O2—C18—H18A	109.5
C10—N1—C7	118.0 (3)	O2—C18—H18B	109.5
C8—N1—C7	113.6 (3)	H18A—C18—H18B	109.5
C3—C2—C1	121.8 (3)	O2—C18—H18C	109.5
C3—C2—H2	119.1	H18A—C18—H18C	109.5
C1—C2—H2	119.1	H18B—C18—H18C	109.5
C13—C19—N3	107.1 (3)	C6—C1—C2	118.9 (3)
C13—C19—C7	131.5 (3)	C6—C1—C9	121.8 (3)
N3—C19—C7	121.2 (3)	C2—C1—C9	119.3 (3)
C1—C6—C5	119.2 (3)	C14—C15—N3	108.2 (3)
C1—C6—C7	121.5 (3)	C14—C15—H15	125.9
C5—C6—C7	119.3 (3)	N3—C15—H15	125.9
O2—C3—C2	125.3 (3)	N1—C8—C9	109.8 (3)
O2—C3—C4	115.0 (3)	N1—C8—H8A	109.7
C2—C3—C4	119.7 (3)	C9—C8—H8A	109.7
C19—C13—C14	108.1 (3)	N1—C8—H8B	109.7
C19—C13—H13	125.9	C9—C8—H8B	109.7
C14—C13—H13	125.9	H8A—C8—H8B	108.2
N1—C7—C19	110.6 (3)	O1—C17—H17A	109.5
N1—C7—C6	110.3 (2)	O1—C17—H17B	109.5
C19—C7—C6	111.7 (3)	H17A—C17—H17B	109.5
N1—C7—H7	108.0	O1—C17—H17C	109.5
C19—C7—H7	108.0	H17A—C17—H17C	109.5
C6—C7—H7	108.0	H17B—C17—H17C	109.5
C1—C9—C8	112.3 (3)	C15—C14—C13	107.2 (3)
C1—C9—H9A	109.1	C15—C14—H14	126.4
C8—C9—H9A	109.1	C13—C14—H14	126.4
C1—C9—H9B	109.1	O3—C11—C12	109.2 (4)
C8—C9—H9B	109.1	O3—C11—H11A	109.8
H9A—C9—H9B	107.9	C12—C11—H11A	109.8
C4—C5—C6	121.8 (3)	O3—C11—H11B	109.8
C4—C5—H5	119.1	C12—C11—H11B	109.8
C6—C5—H5	119.1	H11A—C11—H11B	108.3
C19—N3—C15	109.4 (3)	C11—C12—H12A	109.5
C19—N3—H3	125.3	C11—C12—H12B	109.5
C15—N3—H3	125.3	H12A—C12—H12B	109.5
O4—C10—O3	123.1 (3)	C11—C12—H12C	109.5
O4—C10—N1	125.5 (3)	H12A—C12—H12C	109.5
O3—C10—N1	111.4 (3)	H12B—C12—H12C	109.5

C18—O2—C3—C2	−14.4 (5)	C8—N1—C10—O3	−14.8 (5)
C18—O2—C3—C4	166.3 (3)	C7—N1—C10—O3	−166.0 (3)
C1—C2—C3—O2	−179.6 (3)	C17—O1—C4—C5	7.6 (5)
C1—C2—C3—C4	−0.4 (5)	C17—O1—C4—C3	−172.4 (3)
N3—C19—C13—C14	−0.4 (4)	C6—C5—C4—O1	178.8 (3)
C7—C19—C13—C14	−175.2 (4)	C6—C5—C4—C3	−1.2 (5)
C10—N1—C7—C19	−132.3 (3)	O2—C3—C4—O1	0.6 (5)
C8—N1—C7—C19	74.0 (3)	C2—C3—C4—O1	−178.7 (3)
C10—N1—C7—C6	103.6 (3)	O2—C3—C4—C5	−179.4 (3)
C8—N1—C7—C6	−50.1 (4)	C2—C3—C4—C5	1.3 (5)
C13—C19—C7—N1	−135.5 (4)	C5—C6—C1—C2	0.7 (5)
N3—C19—C7—N1	50.3 (4)	C7—C6—C1—C2	−178.5 (3)
C13—C19—C7—C6	−12.3 (5)	C5—C6—C1—C9	−179.6 (3)
N3—C19—C7—C6	173.6 (3)	C7—C6—C1—C9	1.2 (5)
C1—C6—C7—N1	16.3 (5)	C3—C2—C1—C6	−0.6 (5)
C5—C6—C7—N1	−162.9 (3)	C3—C2—C1—C9	179.7 (3)
C1—C6—C7—C19	−107.1 (4)	C8—C9—C1—C6	12.8 (5)
C5—C6—C7—C19	73.7 (4)	C8—C9—C1—C2	−167.5 (3)
C1—C6—C5—C4	0.2 (5)	C19—N3—C15—C14	−0.5 (4)
C7—C6—C5—C4	179.4 (3)	C10—N1—C8—C9	−86.6 (4)
C13—C19—N3—C15	0.6 (4)	C7—N1—C8—C9	65.8 (4)
C7—C19—N3—C15	176.0 (3)	C1—C9—C8—N1	−44.0 (4)
C11—O3—C10—O4	0.0 (5)	N3—C15—C14—C13	0.2 (5)
C11—O3—C10—N1	−179.1 (3)	C19—C13—C14—C15	0.1 (4)
C8—N1—C10—O4	166.2 (4)	C10—O3—C11—C12	177.0 (4)
C7—N1—C10—O4	15.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.86	2.49	3.225 (4)	145
N3—H3···O2ⁱ	0.86	2.38	3.018 (4)	132
C7—H7···O4	0.98	2.34	2.784 (4)	107
C8—H8B···O3	0.97	2.29	2.653 (4)	101

Symmetry code: (i) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₂O₄
M_r	330.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	290
a, b, c (Å)	8.403 (3), 17.046 (3), 11.6486 (13)
β (°)	95.260 (13)
V (Å³)	1661.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.32 × 0.30

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6852, 3263, 1828
R_int	0.110
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.156, 1.07
No. of reflections	3263
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.86	2.49	3.225 (4)	144.7
N3—H3···O2ⁱ	0.86	2.38	3.018 (4)	131.7
C7—H7···O4	0.98	2.34	2.784 (4)	106.8
C8—H8B···O3	0.97	2.29	2.653 (4)	101.1

Symmetry code: (i) −x, y−1/2, −z+1/2.

Acknowledgements

This work was supported by the National Science Fund of Bulgaria (Project TK357&TK358).

References

Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Kolev, T., Shivachev, B., Petrova, R., Ivanov, I., Atanasova, S. & Statkova, S. (2007). Acta Cryst. E63, o3353–o3354. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Petrova, R., Titorenkova, R. & Shivachev, B. (2007). Acta Cryst. E63, o4751. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rajnikant, Gupta, V. K., Deshmukh, M. B., Varghese, B. & Dinesh (2002). Crystallogr. Rep. 47, 494–496. Google Scholar
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Shishkina, S. V., Shishkin, O. V., Ukrainets, I. V. & Sidorenko, L. V. (2005). Acta Cryst. E61, o4180–o4182. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 64| Part 9| September 2008| Page o1796

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

(±)-Ethyl 6,7-dimeth­­oxy-1-(1H-pyrrol-2-yl)-1,2,3,4-tetra­hydroiso­quinoline-2-car­boxyl­ate

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organic compounds

(±)-Ethyl 6,7-dimethoxy-1-(1H-pyrrol-2-yl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate