(10aS)-7-Methoxy-1,10a-di­hydro­pyrrolo­[1,2-b]­iso­quinoline-3,10(2H,5H)-dione

The crystal structure of the title compound, C₁₃H₁₃NO₃, is stabilized by dipole-dipole and van der Waals forces. The pyrrolidine ring is almost planar, while the central six-membered ring of the indolizine moiety adopts a sofa conformation.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.111
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     -   C3      ..       5.38 su

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               1380
           Count of symmetry unique reflns         1402
           Completeness (_total/calc)             98.43%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(10aS)-7-methoxy-1,10a-dihydropyrrolo[1,2-b]isoquinoline-3,10(2H,5H)-dione

Crystal data

C13H13NO3	F(000) = 244
Mr = 231.24	Dx = 1.357 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 864 reflections
a = 7.423 (1) Å	θ = 3.0–29.9°
b = 7.034 (1) Å	µ = 0.10 mm^−1
c = 10.998 (1) Å	T = 296 K
β = 99.67 (1)°	Block, colorless
V = 566.08 (12) Å^3	0.60 × 0.40 × 0.30 mm
Z = 2

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	864 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 27.5°, θmin = 2.8°
Rotation method data acquisition using ω and φ scans	h = −9→9
3959 measured reflections	k = −9→5
1380 independent reflections	l = −13→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0589P)^2] where P = (Fo^2 + 2Fc^2)/3
1380 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.16 e Å^−3
1 restraint	Δρmin = −0.17 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1774 (4)	0.5473 (6)	0.0832 (3)	0.0772 (10)
H1A	0.1110	0.4599	0.0236	0.093*
H1B	0.0900	0.6222	0.1192	0.093*
C2	0.3005 (5)	0.6756 (6)	0.0219 (3)	0.0807 (10)
H2A	0.2983	0.6378	−0.0632	0.097*
H2B	0.2607	0.8068	0.0233	0.097*
C3	0.4897 (5)	0.6532 (5)	0.0951 (3)	0.0666 (9)
N4	0.4834 (3)	0.5212 (4)	0.1828 (2)	0.0566 (7)
C5	0.6373 (3)	0.4630 (6)	0.2731 (2)	0.0599 (7)
H5A	0.7385	0.5495	0.2709	0.072*
H5B	0.6758	0.3368	0.2529	0.072*
C6	0.7282 (3)	0.4591 (4)	0.5027 (2)	0.0496 (6)
H6	0.8498	0.4587	0.4919	0.060*
C7	0.6842 (3)	0.4571 (5)	0.6206 (2)	0.0521 (6)
C8	0.5028 (4)	0.4571 (5)	0.6370 (2)	0.0585 (7)
H8	0.4742	0.4567	0.7162	0.070*
C9	0.3668 (3)	0.4577 (5)	0.5371 (3)	0.0579 (7)
H9	0.2456	0.4574	0.5488	0.069*
C10	0.2540 (3)	0.4516 (5)	0.3109 (2)	0.0566 (7)
C11	0.5891 (3)	0.4616 (4)	0.4009 (2)	0.0442 (6)
C12	0.4070 (3)	0.4589 (4)	0.4165 (2)	0.0467 (6)
C13	0.3048 (3)	0.4383 (5)	0.1836 (2)	0.0566 (7)
H13	0.3074	0.3042	0.1597	0.068*
C14	0.9993 (4)	0.4509 (7)	0.7154 (3)	0.0850 (11)
H14A	1.0725	0.4512	0.7961	0.128*
H14B	1.0280	0.5609	0.6705	0.128*
H14C	1.0245	0.3380	0.6721	0.128*
O15	0.6272 (4)	0.7407 (4)	0.0806 (2)	0.0934 (9)
O16	0.8097 (3)	0.4548 (4)	0.72636 (16)	0.0760 (6)
O17	0.0945 (2)	0.4473 (4)	0.3246 (2)	0.0870 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0590 (18)	0.108 (3)	0.0630 (19)	0.005 (2)	0.0056 (15)	−0.007 (2)
C2	0.083 (2)	0.085 (2)	0.067 (2)	0.001 (2)	−0.0077 (19)	0.001 (2)
C3	0.071 (2)	0.081 (2)	0.0474 (17)	−0.008 (2)	0.0093 (15)	−0.0047 (18)
N4	0.0463 (12)	0.0768 (18)	0.0470 (12)	−0.0035 (12)	0.0085 (10)	0.0064 (13)
C5	0.0456 (14)	0.083 (2)	0.0531 (14)	−0.0005 (18)	0.0133 (11)	0.0045 (18)
C6	0.0468 (13)	0.0509 (15)	0.0534 (14)	−0.0006 (16)	0.0148 (11)	0.0041 (17)
C7	0.0620 (15)	0.0495 (15)	0.0469 (14)	0.0024 (17)	0.0151 (12)	0.0033 (16)
C8	0.0706 (17)	0.0584 (16)	0.0530 (15)	0.0066 (19)	0.0287 (14)	0.0050 (17)
C9	0.0534 (14)	0.0588 (16)	0.0678 (17)	0.0043 (18)	0.0285 (13)	0.0085 (18)
C10	0.0474 (14)	0.0575 (16)	0.0669 (18)	0.0010 (17)	0.0151 (12)	0.0073 (18)
C11	0.0455 (13)	0.0409 (14)	0.0493 (13)	0.0010 (15)	0.0169 (11)	0.0041 (16)
C12	0.0474 (13)	0.0412 (14)	0.0543 (14)	−0.0008 (15)	0.0167 (11)	0.0039 (16)
C13	0.0457 (14)	0.0636 (18)	0.0609 (16)	−0.0047 (16)	0.0098 (12)	−0.0047 (17)
C14	0.0652 (18)	0.128 (3)	0.0596 (18)	0.002 (3)	0.0029 (14)	0.003 (2)
O15	0.0895 (17)	0.119 (2)	0.0703 (14)	−0.0320 (17)	0.0107 (12)	0.0209 (14)
O16	0.0701 (12)	0.1108 (17)	0.0478 (10)	0.0047 (16)	0.0119 (9)	0.0022 (14)
O17	0.0448 (10)	0.130 (2)	0.0899 (14)	−0.0028 (15)	0.0211 (10)	0.0148 (17)

Geometric parameters (Å, º)

C1—C2	1.520 (5)	C6—H6	0.9300
C1—C13	1.533 (4)	C7—O16	1.363 (3)
C1—H1A	0.9700	C7—C8	1.389 (3)
C1—H1B	0.9700	C8—C9	1.361 (4)
C2—C3	1.505 (5)	C8—H8	0.9300
C2—H2A	0.9700	C9—C12	1.408 (3)
C2—H2B	0.9700	C9—H9	0.9300
C3—O15	1.225 (4)	C10—O17	1.219 (3)
C3—N4	1.345 (4)	C10—C12	1.482 (3)
N4—C5	1.441 (3)	C10—C13	1.513 (4)
N4—C13	1.450 (3)	C11—C12	1.391 (3)
C5—C11	1.508 (3)	C13—H13	0.9800
C5—H5A	0.9700	C14—O16	1.433 (3)
C5—H5B	0.9700	C14—H14A	0.9600
C6—C11	1.389 (3)	C14—H14B	0.9600
C6—C7	1.390 (4)	C14—H14C	0.9600
C2—C1—C13	105.8 (2)	C8—C7—C6	120.4 (2)
C2—C1—H1A	110.6	C9—C8—C7	119.9 (2)
C13—C1—H1A	110.6	C9—C8—H8	120.0
C2—C1—H1B	110.6	C7—C8—H8	120.0
C13—C1—H1B	110.6	C8—C9—C12	121.0 (2)
H1A—C1—H1B	108.7	C8—C9—H9	119.5
C3—C2—C1	106.1 (3)	C12—C9—H9	119.5
C3—C2—H2A	110.5	O17—C10—C12	122.4 (2)
C1—C2—H2A	110.5	O17—C10—C13	120.7 (2)
C3—C2—H2B	110.5	C12—C10—C13	116.8 (2)
C1—C2—H2B	110.5	C6—C11—C12	120.4 (2)
H2A—C2—H2B	108.7	C6—C11—C5	119.4 (2)
O15—C3—N4	124.7 (3)	C12—C11—C5	120.1 (2)
O15—C3—C2	126.9 (3)	C11—C12—C9	118.7 (2)
N4—C3—C2	108.3 (3)	C11—C12—C10	122.4 (2)
C3—N4—C5	124.8 (2)	C9—C12—C10	118.9 (2)
C3—N4—C13	115.1 (2)	N4—C13—C10	110.5 (2)
C5—N4—C13	120.1 (2)	N4—C13—C1	104.4 (3)
N4—C5—C11	111.1 (2)	C10—C13—C1	114.6 (2)
N4—C5—H5A	109.4	N4—C13—H13	109.0
C11—C5—H5A	109.4	C10—C13—H13	109.0
N4—C5—H5B	109.4	C1—C13—H13	109.0
C11—C5—H5B	109.4	O16—C14—H14A	109.5
H5A—C5—H5B	108.0	O16—C14—H14B	109.5
C11—C6—C7	119.5 (2)	H14A—C14—H14B	109.5
C11—C6—H6	120.2	O16—C14—H14C	109.5
C7—C6—H6	120.2	H14A—C14—H14C	109.5
O16—C7—C8	115.4 (2)	H14B—C14—H14C	109.5
O16—C7—C6	124.2 (2)	C7—O16—C14	117.9 (2)
C13—C1—C2—C3	−5.6 (4)	C6—C11—C12—C10	−176.8 (3)
C1—C2—C3—O15	−175.4 (3)	C5—C11—C12—C10	1.8 (5)
C1—C2—C3—N4	3.5 (4)	C8—C9—C12—C11	−0.7 (5)
O15—C3—N4—C5	0.1 (5)	C8—C9—C12—C10	177.5 (3)
C2—C3—N4—C5	−178.8 (3)	O17—C10—C12—C11	179.3 (3)
O15—C3—N4—C13	179.1 (3)	C13—C10—C12—C11	2.6 (5)
C2—C3—N4—C13	0.2 (4)	O17—C10—C12—C9	1.1 (6)
C3—N4—C5—C11	131.8 (3)	C13—C10—C12—C9	−175.6 (3)
C13—N4—C5—C11	−47.2 (4)	C3—N4—C13—C10	−127.5 (3)
C11—C6—C7—O16	−179.9 (3)	C5—N4—C13—C10	51.5 (4)
C11—C6—C7—C8	0.2 (5)	C3—N4—C13—C1	−3.8 (3)
O16—C7—C8—C9	−179.5 (3)	C5—N4—C13—C1	175.3 (2)
C6—C7—C8—C9	0.5 (5)	O17—C10—C13—N4	156.8 (3)
C7—C8—C9—C12	−0.2 (6)	C12—C10—C13—N4	−26.5 (4)
C7—C6—C11—C12	−1.1 (5)	O17—C10—C13—C1	39.2 (5)
C7—C6—C11—C5	−179.8 (3)	C12—C10—C13—C1	−144.2 (3)
N4—C5—C11—C6	−163.0 (3)	C2—C1—C13—N4	5.6 (3)
N4—C5—C11—C12	18.3 (4)	C2—C1—C13—C10	126.6 (3)
C6—C11—C12—C9	1.4 (5)	C8—C7—O16—C14	178.8 (3)
C5—C11—C12—C9	−180.0 (3)	C6—C7—O16—C14	−1.1 (5)