(S)-Ethyl 1,2,3,9-tetra-hydro-pyrrolo[2,1-b]quinazoline-1-carboxyl-ate.

The title chiral compound, C(14)H(16)N(2)O(2), was prepared by esterification of (S)-1,2,3,9-tetra-hydro-pyrrolo[2,1-b]quinazol-in-1-carboxylic acid in the presence of HCl/EtOH. In the mol-ecule, the quinazoline ring is non-planar and exhibits a distorted half-chair conformation, while the five-membered ring shows a typical envelope conformation. Inter-molecular C-H⋯N hydrogen bonding helps to stabilize the crystal structure.

Related literature

For general background, see: Cheng et al. (2006 ▶); Hua et al. (2002 ▶).

Experimental

Crystal data

C14H16N2O2

M = 244.29

Monoclinic,

a = 6.0545 (8) Å

b = 9.1438 (13) Å

c = 11.5228 (16) Å

β = 92.905 (2)°

V = 637.10 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 187 (2) K

0.29 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

3430 measured reflections

1246 independent reflections

1166 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.076

S = 1.08

1246 reflections

164 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008908/xu2409sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008908/xu2409Isup2.hkl

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

C14H16N2O2	F000 = 260
Mr = 244.29	Dx = 1.273 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1588 reflections
a = 6.0545 (8) Å	θ = 2.9–25.0º
b = 9.1438 (13) Å	µ = 0.09 mm−1
c = 11.5228 (16) Å	T = 187 (2) K
β = 92.905 (2)º	Block, colorless
V = 637.10 (15) Å3	0.29 × 0.22 × 0.19 mm
Z = 2

Bruker SMART APEX CCD area-detector diffractometer	1166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Monochromator: graphite	θmax = 25.4º
T = 187(2) K	θmin = 1.8º
φ and ω scans	h = −7→7
Absorption correction: none	k = −11→5
3430 measured reflections	l = −13→13
1246 independent reflections

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0381P)2 + 0.082P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
1246 reflections	Δρmax = 0.11 e Å−3
164 parameters	Δρmin = −0.14 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
C1	0.8935 (4)	0.4244 (2)	0.24523 (19)	0.0343 (5)
H1A	0.9134	0.4636	0.3252	0.041*
H1B	0.7364	0.4369	0.2188	0.041*
C2	1.0401 (3)	0.5062 (2)	0.16534 (17)	0.0301 (5)
C3	0.9824 (4)	0.6432 (3)	0.12309 (18)	0.0360 (5)
H3	0.8452	0.6850	0.1421	0.043*
C4	1.1216 (4)	0.7206 (3)	0.05344 (18)	0.0403 (5)
H4	1.0813	0.8155	0.0263	0.048*
C5	1.3199 (4)	0.6585 (3)	0.02377 (18)	0.0385 (5)
H5	1.4157	0.7105	−0.0244	0.046*
C6	1.3781 (4)	0.5209 (3)	0.06430 (18)	0.0348 (5)
H6	1.5135	0.4786	0.0430	0.042*
C7	1.2412 (3)	0.4433 (2)	0.13602 (16)	0.0295 (5)
C8	1.1581 (3)	0.2248 (3)	0.22061 (16)	0.0309 (5)
C9	1.1809 (4)	0.0669 (3)	0.2550 (2)	0.0413 (6)
H9A	1.2678	0.0565	0.3297	0.050*
H9B	1.2532	0.0098	0.1946	0.050*
C10	0.9409 (4)	0.0170 (3)	0.2667 (2)	0.0428 (6)
H10A	0.9307	−0.0560	0.3297	0.051*
H10B	0.8795	−0.0261	0.1931	0.051*
C11	0.8183 (3)	0.1590 (3)	0.29605 (17)	0.0351 (5)
H11	0.6653	0.1587	0.2590	0.042*
C12	0.8108 (4)	0.1795 (3)	0.42708 (19)	0.0387 (6)
C13	0.6211 (4)	0.1044 (4)	0.5926 (2)	0.0562 (8)
H13A	0.7692	0.1147	0.6322	0.067*
H13B	0.5573	0.0102	0.6169	0.067*
C14	0.4776 (5)	0.2258 (4)	0.6279 (2)	0.0595 (7)
H14A	0.3311	0.2158	0.5886	0.089*
H14B	0.5433	0.3193	0.6063	0.089*
H14C	0.4636	0.2228	0.7123	0.089*
N1	0.9521 (3)	0.2705 (2)	0.24410 (14)	0.0315 (4)
N2	1.3078 (3)	0.3013 (2)	0.17238 (15)	0.0328 (4)
O1	0.6431 (3)	0.1034 (2)	0.46705 (14)	0.0454 (4)
O2	0.9396 (3)	0.2508 (3)	0.48572 (14)	0.0652 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0276 (11)	0.0351 (13)	0.0405 (11)	0.0037 (10)	0.0048 (9)	−0.0020 (10)
C2	0.0287 (10)	0.0315 (12)	0.0298 (10)	−0.0010 (9)	−0.0006 (8)	−0.0023 (9)
C3	0.0340 (11)	0.0361 (12)	0.0380 (11)	0.0045 (10)	0.0007 (9)	−0.0005 (10)
C4	0.0511 (14)	0.0309 (12)	0.0383 (11)	0.0021 (11)	−0.0026 (10)	0.0044 (11)
C5	0.0450 (12)	0.0389 (13)	0.0316 (11)	−0.0062 (11)	0.0036 (9)	0.0033 (10)
C6	0.0296 (10)	0.0399 (13)	0.0351 (11)	−0.0049 (10)	0.0042 (9)	−0.0039 (11)
C7	0.0276 (10)	0.0320 (12)	0.0285 (10)	0.0003 (9)	−0.0014 (8)	−0.0011 (9)
C8	0.0282 (10)	0.0337 (11)	0.0307 (10)	0.0034 (10)	0.0013 (8)	−0.0002 (9)
C9	0.0376 (12)	0.0370 (14)	0.0495 (14)	0.0034 (11)	0.0055 (10)	0.0055 (10)
C10	0.0451 (14)	0.0366 (13)	0.0471 (13)	−0.0041 (11)	0.0065 (11)	0.0043 (11)
C11	0.0279 (10)	0.0412 (13)	0.0361 (11)	−0.0061 (10)	0.0011 (8)	0.0062 (10)
C12	0.0308 (11)	0.0479 (15)	0.0372 (11)	0.0032 (10)	0.0001 (9)	0.0092 (10)
C13	0.0580 (16)	0.073 (2)	0.0391 (13)	0.0063 (16)	0.0170 (12)	0.0200 (14)
C14	0.0631 (16)	0.0670 (18)	0.0495 (14)	−0.0021 (16)	0.0120 (12)	−0.0016 (15)
N1	0.0274 (9)	0.0328 (11)	0.0347 (9)	0.0008 (8)	0.0050 (7)	0.0042 (8)
N2	0.0260 (9)	0.0347 (11)	0.0380 (9)	0.0017 (8)	0.0046 (7)	0.0019 (8)
O1	0.0442 (9)	0.0514 (11)	0.0418 (9)	−0.0038 (8)	0.0140 (7)	0.0093 (8)
O2	0.0519 (11)	0.1046 (18)	0.0385 (9)	−0.0257 (12)	−0.0036 (8)	0.0003 (11)

C1—N1	1.452 (3)	C9—C10	1.536 (3)
C1—C2	1.509 (3)	C9—H9A	0.9900
C1—H1A	0.9900	C9—H9B	0.9900
C1—H1B	0.9900	C10—C11	1.541 (4)
C2—C3	1.383 (3)	C10—H10A	0.9900
C2—C7	1.403 (3)	C10—H10B	0.9900
C3—C4	1.387 (3)	C11—N1	1.450 (3)
C3—H3	0.9500	C11—C12	1.524 (3)
C4—C5	1.387 (3)	C11—H11	1.0000
C4—H4	0.9500	C12—O2	1.199 (3)
C5—C6	1.381 (3)	C12—O1	1.332 (3)
C5—H5	0.9500	C13—O1	1.459 (3)
C6—C7	1.394 (3)	C13—C14	1.480 (4)
C6—H6	0.9500	C13—H13A	0.9900
C7—N2	1.416 (3)	C13—H13B	0.9900
C8—N2	1.293 (3)	C14—H14A	0.9800
C8—N1	1.355 (3)	C14—H14B	0.9800
C8—C9	1.502 (3)	C14—H14C	0.9800
N1—C1—C2	108.86 (17)	C9—C10—C11	103.7 (2)
N1—C1—H1A	109.9	C9—C10—H10A	111.0
C2—C1—H1A	109.9	C11—C10—H10A	111.0
N1—C1—H1B	109.9	C9—C10—H10B	111.0
C2—C1—H1B	109.9	C11—C10—H10B	111.0
H1A—C1—H1B	108.3	H10A—C10—H10B	109.0
C3—C2—C7	119.57 (19)	N1—C11—C12	111.57 (19)
C3—C2—C1	121.18 (19)	N1—C11—C10	102.49 (17)
C7—C2—C1	119.23 (18)	C12—C11—C10	111.05 (18)
C2—C3—C4	121.1 (2)	N1—C11—H11	110.5
C2—C3—H3	119.5	C12—C11—H11	110.5
C4—C3—H3	119.5	C10—C11—H11	110.5
C5—C4—C3	119.5 (2)	O2—C12—O1	125.1 (2)
C5—C4—H4	120.2	O2—C12—C11	125.0 (2)
C3—C4—H4	120.2	O1—C12—C11	109.86 (19)
C6—C5—C4	119.9 (2)	O1—C13—C14	111.2 (2)
C6—C5—H5	120.0	O1—C13—H13A	109.4
C4—C5—H5	120.0	C14—C13—H13A	109.4
C5—C6—C7	121.0 (2)	O1—C13—H13B	109.4
C5—C6—H6	119.5	C14—C13—H13B	109.4
C7—C6—H6	119.5	H13A—C13—H13B	108.0
C6—C7—C2	118.89 (19)	C13—C14—H14A	109.5
C6—C7—N2	118.26 (19)	C13—C14—H14B	109.5
C2—C7—N2	122.80 (18)	H14A—C14—H14B	109.5
N2—C8—N1	126.3 (2)	C13—C14—H14C	109.5
N2—C8—C9	125.2 (2)	H14A—C14—H14C	109.5
N1—C8—C9	108.43 (19)	H14B—C14—H14C	109.5
C8—C9—C10	103.55 (19)	C8—N1—C11	113.89 (18)
C8—C9—H9A	111.0	C8—N1—C1	121.87 (18)
C10—C9—H9A	111.1	C11—N1—C1	122.40 (17)
C8—C9—H9B	111.1	C8—N2—C7	115.34 (18)
C10—C9—H9B	111.1	C12—O1—C13	116.7 (2)
H9A—C9—H9B	109.0

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2i	0.95	2.59	3.523 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2i	0.95	2.59	3.523 (3)	169

Symmetry code: (i) .