1-Meth­yl-6,7-dihydro­pyrrolo[2,3-c]azepine-4,8(1H,5H)-dione

The title compound, C₉H₁₀N₂O₂, was synthesized by cyclization of 3-(1-methyl­pyrrole-2-carboxamido)propanoic acid in the presence of phospho­rus oxychloride. Inter­molecular N—H...O hydrogen bonds generate a one-dimensional chain in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.088
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



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           27.05
           From the CIF: _reflns_number_total               1088
           Count of symmetry unique reflns         1096
           Completeness (_total/calc)             99.27%
           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
   0 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
   0 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

---

Computing details

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

1-Methyl-6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione

Crystal data

C9H10N2O2	Dx = 1.395 Mg m^−3
Mr = 178.19	Melting point: 471 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 863 reflections
a = 8.589 (3) Å	θ = 3.0–26.9°
b = 8.686 (3) Å	µ = 0.10 mm^−1
c = 11.375 (4) Å	T = 273 K
V = 848.6 (5) Å^3	Block, pale yellow
Z = 4	0.50 × 0.37 × 0.24 mm
F(000) = 376

Data collection

Bruker SMART 1K CCD area-detector diffractometer	1088 independent reflections
Radiation source: fine-focus sealed tube	991 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 27.1°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	h = −11→10
Tmin = 0.953, Tmax = 0.986	k = −11→11
5343 measured reflections	l = −11→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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0557P)^2 + 0.1067P] where P = (Fo^2 + 2Fc^2)/3
1088 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.04462 (17)	0.86100 (16)	0.20396 (14)	0.0553 (4)
O2	0.4332 (2)	0.41611 (16)	0.40611 (13)	0.0603 (4)
C1	0.3491 (3)	0.8785 (2)	0.48757 (17)	0.0486 (5)
H1	0.3693	0.9474	0.5482	0.058*
C2	0.3976 (2)	0.7293 (2)	0.48375 (17)	0.0463 (5)
H2	0.4548	0.6780	0.5411	0.056*
C3	0.3444 (2)	0.6670 (2)	0.37587 (16)	0.0377 (4)
C4	0.2610 (2)	0.78326 (19)	0.31886 (15)	0.0360 (4)
C5	0.1620 (2)	0.78013 (19)	0.21187 (16)	0.0381 (4)
C6	0.3399 (2)	0.5856 (2)	0.12434 (16)	0.0421 (4)
H6A	0.4318	0.6481	0.1375	0.051*
H6B	0.3491	0.5396	0.0469	0.051*
C7	0.3353 (3)	0.4587 (2)	0.21540 (18)	0.0442 (4)
H7A	0.2319	0.4138	0.2155	0.053*
H7B	0.4079	0.3788	0.1922	0.053*
C8	0.3740 (2)	0.5086 (2)	0.33844 (16)	0.0396 (4)
C9	0.2061 (3)	1.0644 (2)	0.3625 (2)	0.0588 (6)
H9A	0.2253	1.1314	0.4280	0.088*
H9B	0.0961	1.0582	0.3482	0.088*
H9C	0.2572	1.1043	0.2939	0.088*
N1	0.26655 (19)	0.91067 (17)	0.38880 (14)	0.0415 (4)
N2	0.20374 (18)	0.68391 (18)	0.12651 (14)	0.0427 (4)
H2A	0.1435	0.6796	0.0662	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0505 (8)	0.0500 (8)	0.0654 (9)	0.0118 (7)	−0.0083 (7)	−0.0023 (7)
O2	0.0819 (11)	0.0502 (8)	0.0490 (8)	0.0186 (8)	0.0033 (8)	0.0124 (7)
C1	0.0553 (11)	0.0513 (10)	0.0394 (9)	−0.0077 (10)	0.0038 (9)	−0.0100 (9)
C2	0.0528 (11)	0.0521 (11)	0.0341 (9)	−0.0020 (9)	−0.0011 (8)	0.0020 (8)
C3	0.0400 (8)	0.0388 (8)	0.0343 (8)	−0.0020 (8)	0.0036 (7)	0.0030 (7)
C4	0.0371 (8)	0.0327 (8)	0.0382 (9)	−0.0030 (7)	0.0060 (7)	−0.0001 (7)
C5	0.0379 (8)	0.0341 (8)	0.0424 (9)	−0.0019 (8)	0.0006 (7)	0.0053 (7)
C6	0.0449 (9)	0.0466 (9)	0.0350 (8)	0.0019 (9)	0.0050 (8)	−0.0042 (8)
C7	0.0487 (10)	0.0370 (8)	0.0470 (10)	0.0027 (8)	0.0041 (9)	−0.0040 (8)
C8	0.0419 (10)	0.0377 (8)	0.0393 (9)	0.0026 (8)	0.0072 (7)	0.0071 (8)
C9	0.0639 (13)	0.0349 (9)	0.0776 (16)	0.0030 (9)	0.0029 (12)	−0.0073 (10)
N1	0.0448 (8)	0.0360 (7)	0.0436 (8)	−0.0006 (7)	0.0061 (7)	−0.0058 (7)
N2	0.0455 (8)	0.0468 (8)	0.0357 (8)	0.0018 (7)	−0.0047 (6)	−0.0003 (7)

Geometric parameters (Å, º)

O1—C5	1.232 (2)	C6—N2	1.448 (2)
O2—C8	1.223 (2)	C6—C7	1.513 (3)
C1—N1	1.358 (3)	C6—H6A	0.9700
C1—C2	1.362 (3)	C6—H6B	0.9700
C1—H1	0.9300	C7—C8	1.502 (3)
C2—C3	1.417 (3)	C7—H7A	0.9700
C2—H2	0.9300	C7—H7B	0.9700
C3—C4	1.398 (2)	C9—N1	1.463 (2)
C3—C8	1.462 (2)	C9—H9A	0.9600
C4—N1	1.364 (2)	C9—H9B	0.9600
C4—C5	1.485 (3)	C9—H9C	0.9600
C5—N2	1.330 (2)	N2—H2A	0.8600
N1—C1—C2	109.23 (17)	C8—C7—C6	114.97 (15)
N1—C1—H1	125.4	C8—C7—H7A	108.5
C2—C1—H1	125.4	C6—C7—H7A	108.5
C1—C2—C3	107.00 (18)	C8—C7—H7B	108.5
C1—C2—H2	126.5	C6—C7—H7B	108.5
C3—C2—H2	126.5	H7A—C7—H7B	107.5
C4—C3—C2	106.92 (16)	O2—C8—C3	120.47 (17)
C4—C3—C8	129.35 (17)	O2—C8—C7	119.26 (17)
C2—C3—C8	123.73 (17)	C3—C8—C7	120.25 (16)
N1—C4—C3	107.34 (16)	N1—C9—H9A	109.5
N1—C4—C5	120.86 (15)	N1—C9—H9B	109.5
C3—C4—C5	131.33 (16)	H9A—C9—H9B	109.5
O1—C5—N2	121.70 (18)	N1—C9—H9C	109.5
O1—C5—C4	121.20 (17)	H9A—C9—H9C	109.5
N2—C5—C4	117.09 (15)	H9B—C9—H9C	109.5
N2—C6—C7	113.37 (15)	C1—N1—C4	109.49 (15)
N2—C6—H6A	108.9	C1—N1—C9	122.87 (17)
C7—C6—H6A	108.9	C4—N1—C9	127.48 (17)
N2—C6—H6B	108.9	C5—N2—C6	126.91 (15)
C7—C6—H6B	108.9	C5—N2—H2A	116.5
H6A—C6—H6B	107.7	C6—N2—H2A	116.5
N1—C1—C2—C3	1.1 (2)	C4—C3—C8—C7	10.5 (3)
C1—C2—C3—C4	−1.3 (2)	C2—C3—C8—C7	−170.54 (18)
C1—C2—C3—C8	179.56 (17)	C6—C7—C8—O2	−151.04 (18)
C2—C3—C4—N1	1.0 (2)	C6—C7—C8—C3	27.6 (3)
C8—C3—C4—N1	−179.88 (17)	C2—C1—N1—C4	−0.4 (2)
C2—C3—C4—C5	−170.87 (18)	C2—C1—N1—C9	−176.17 (19)
C8—C3—C4—C5	8.2 (3)	C3—C4—N1—C1	−0.4 (2)
N1—C4—C5—O1	−26.5 (3)	C5—C4—N1—C1	172.52 (16)
C3—C4—C5—O1	144.5 (2)	C3—C4—N1—C9	175.10 (18)
N1—C4—C5—N2	154.99 (17)	C5—C4—N1—C9	−12.0 (3)
C3—C4—C5—N2	−34.0 (3)	O1—C5—N2—C6	178.71 (16)
N2—C6—C7—C8	−77.9 (2)	C4—C5—N2—C6	−2.8 (3)
C4—C3—C8—O2	−170.83 (19)	C7—C6—N2—C5	66.9 (2)
C2—C3—C8—O2	8.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2^i	0.86	2.11	2.902 (2)	153

Symmetry code: (i) −x+1/2, −y+1, z−1/2.