Methyl 2-acetamido-2-(1-acetyl-3-hydr-oxy-2-oxoindolin-3-yl)propanoate.

In the title isatin compound, C(16)H(18)N(2)O(6), the pyrrolidine ring adopts an envelope conformation and is inclined at a dihedral angle of 7.31 (5)° with respect to the benzene ring. The acetyl group is disordered over two positions with refined occupancies of 0.503 (4) and 0.497 (4). These groups make dihedral angles of 12.6 (6) and 19.6 (7)° with the pyrrolidine ring. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link neighbouring mol-ecules into infinite chains along the b axis. These chains are further inter-connected by inter-molecular O-H⋯O hydrogen bonds into two-dimensional arrays parallel to the bc plane. Weak inter-molecular C-H⋯π inter-actions further stabilize the crystal structure.

Related literature

For general background to and applications of isatin derivatives, see: Chu et al. (2007 ▶); Glover & Bhattacharya (1991 ▶); Gursoy & Karali (1996 ▶); Pandeya et al. (1998 ▶); Patel et al. (2006 ▶); Popp (1975 ▶); Shvekhgeimer (1996 ▶); Sriram et al. (2006 ▶); Verma et al. (2004 ▶); Vine et al. (2007 ▶). For photoreactions of N-acetyl­isatin, see: Zhang et al. (2004 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For related structures, see: Usman et al. (2001 ▶, 2002 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H18N2O6

M = 334.32

Monoclinic,

a = 28.4345 (6) Å

b = 8.3396 (2) Å

c = 14.3779 (3) Å

β = 114.351 (2)°

V = 3106.15 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.47 × 0.37 × 0.26 mm

Data collection

Bruker SMART APEX Duo CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.950, T max = 0.972

39997 measured reflections

5705 independent reflections

4854 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.126

S = 1.03

5705 reflections

258 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007270/sj2735sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007270/sj2735Isup2.hkl

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

C16H18N2O6	F(000) = 1408
Mr = 334.32	Dx = 1.430 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9185 reflections
a = 28.4345 (6) Å	θ = 2.6–32.6°
b = 8.3396 (2) Å	µ = 0.11 mm−1
c = 14.3779 (3) Å	T = 100 K
β = 114.351 (2)°	Block, colourless
V = 3106.15 (12) Å3	0.47 × 0.37 × 0.26 mm
Z = 8

Bruker SMART APEX Duo CCD area-detector diffractometer	5705 independent reflections
Radiation source: fine-focus sealed tube	4854 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 32.7°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −42→43
Tmin = 0.950, Tmax = 0.972	k = −12→12
39997 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0685P)2 + 1.8239P] where P = (Fo2 + 2Fc2)/3
5705 reflections	(Δ/σ)max < 0.001
258 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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	Occ. (<1)
O1	0.18064 (3)	0.48686 (8)	−0.01504 (5)	0.02081 (14)
O2	0.07223 (3)	0.53296 (9)	−0.06871 (6)	0.02680 (16)
O4	0.16093 (3)	0.21913 (9)	0.24294 (6)	0.02902 (17)
O5	0.08943 (3)	0.35325 (9)	0.14131 (6)	0.02432 (15)
O6	0.15655 (4)	0.58921 (10)	0.29251 (6)	0.03130 (18)
N1	0.07133 (3)	0.25274 (11)	−0.07079 (8)	0.0300 (2)
N2	0.15337 (3)	0.59960 (9)	0.13473 (6)	0.01608 (14)
C1	0.11099 (4)	0.13422 (11)	−0.04580 (7)	0.01937 (17)
C2	0.10601 (4)	−0.02706 (11)	−0.07223 (7)	0.02217 (18)
H2A	0.0737	−0.0746	−0.1052	0.027*
C3	0.15133 (4)	−0.11480 (11)	−0.04742 (7)	0.02182 (18)
H3A	0.1492	−0.2230	−0.0643	0.026*
C4	0.19967 (4)	−0.04441 (11)	0.00189 (8)	0.02254 (18)
H4A	0.2293	−0.1054	0.0169	0.027*
C5	0.20390 (4)	0.11744 (11)	0.02897 (7)	0.01982 (17)
H5A	0.2361	0.1650	0.0621	0.024*
C6	0.15917 (3)	0.20604 (10)	0.00553 (6)	0.01592 (15)
C7	0.15271 (3)	0.38261 (10)	0.02069 (6)	0.01522 (15)
C8	0.09386 (4)	0.40548 (11)	−0.04325 (7)	0.02089 (17)
O3A	0.0031 (3)	0.0870 (9)	−0.1455 (7)	0.068 (2)	0.503 (4)
C9A	0.01989 (9)	0.2274 (3)	−0.1348 (3)	0.0290 (5)	0.503 (4)
C10A	−0.01576 (8)	0.3669 (3)	−0.17624 (17)	0.0287 (5)	0.503 (4)
H10A	−0.0488	0.3293	−0.2242	0.043*	0.503 (4)
H10B	−0.0016	0.4393	−0.2099	0.043*	0.503 (4)
H10C	−0.0198	0.4216	−0.1212	0.043*	0.503 (4)
O3B	0.0045 (3)	0.0780 (10)	−0.1114 (8)	0.097 (3)	0.497 (4)
C9B	0.01733 (9)	0.2087 (3)	−0.0877 (3)	0.0343 (6)	0.497 (4)
C10B	−0.01742 (8)	0.3377 (3)	−0.0815 (2)	0.0339 (6)	0.497 (4)
H10D	−0.0347	0.3870	−0.1473	0.051*	0.497 (4)
H10E	0.0026	0.4169	−0.0328	0.051*	0.497 (4)
H10F	−0.0425	0.2924	−0.0605	0.051*	0.497 (4)
C11	0.16854 (3)	0.43179 (10)	0.13503 (6)	0.01508 (14)
C12	0.14032 (4)	0.32345 (11)	0.18209 (7)	0.01931 (16)
C13	0.05969 (6)	0.25468 (15)	0.18069 (14)	0.0438 (3)
H13A	0.0236	0.2769	0.1434	0.066*
H13B	0.0696	0.2785	0.2516	0.066*
H13C	0.0661	0.1435	0.1731	0.066*
C14	0.15038 (3)	0.66917 (11)	0.21616 (7)	0.01811 (16)
C15	0.13850 (4)	0.84545 (11)	0.20910 (8)	0.02441 (19)
H15A	0.1577	0.8950	0.2741	0.037*
H15B	0.1022	0.8606	0.1901	0.037*
H15C	0.1480	0.8934	0.1586	0.037*
C16	0.22685 (4)	0.41480 (12)	0.19614 (7)	0.02257 (18)
H16A	0.2363	0.4557	0.2639	0.034*
H16B	0.2446	0.4743	0.1632	0.034*
H16C	0.2363	0.3037	0.1997	0.034*
H1O1	0.1751 (7)	0.467 (2)	−0.0785 (13)	0.043 (4)*
H1N2	0.1491 (6)	0.658 (2)	0.0803 (13)	0.037 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0311 (3)	0.0154 (3)	0.0206 (3)	−0.0004 (2)	0.0154 (3)	0.0001 (2)
O2	0.0279 (4)	0.0212 (3)	0.0225 (3)	0.0096 (3)	0.0016 (3)	−0.0024 (3)
O4	0.0417 (4)	0.0207 (3)	0.0283 (4)	0.0071 (3)	0.0181 (3)	0.0091 (3)
O5	0.0234 (3)	0.0183 (3)	0.0349 (4)	−0.0014 (2)	0.0156 (3)	0.0029 (3)
O6	0.0504 (5)	0.0266 (4)	0.0169 (3)	0.0064 (3)	0.0138 (3)	0.0000 (3)
N1	0.0182 (4)	0.0203 (4)	0.0376 (5)	0.0029 (3)	−0.0025 (3)	−0.0127 (3)
N2	0.0207 (3)	0.0119 (3)	0.0159 (3)	0.0007 (2)	0.0078 (3)	−0.0004 (2)
C1	0.0213 (4)	0.0154 (4)	0.0192 (4)	0.0019 (3)	0.0061 (3)	−0.0038 (3)
C2	0.0280 (4)	0.0162 (4)	0.0220 (4)	−0.0012 (3)	0.0099 (3)	−0.0047 (3)
C3	0.0344 (5)	0.0127 (3)	0.0223 (4)	0.0018 (3)	0.0157 (4)	−0.0003 (3)
C4	0.0289 (4)	0.0154 (4)	0.0277 (4)	0.0062 (3)	0.0162 (4)	0.0022 (3)
C5	0.0221 (4)	0.0163 (4)	0.0232 (4)	0.0034 (3)	0.0114 (3)	0.0008 (3)
C6	0.0194 (4)	0.0129 (3)	0.0154 (3)	0.0019 (3)	0.0072 (3)	−0.0005 (3)
C7	0.0176 (3)	0.0124 (3)	0.0147 (3)	0.0015 (3)	0.0058 (3)	−0.0008 (3)
C8	0.0203 (4)	0.0183 (4)	0.0178 (4)	0.0034 (3)	0.0015 (3)	−0.0054 (3)
O3A	0.031 (2)	0.0249 (15)	0.107 (3)	−0.0043 (12)	−0.012 (2)	−0.0154 (19)
C9A	0.0171 (9)	0.0259 (10)	0.0374 (14)	−0.0030 (7)	0.0044 (9)	−0.0101 (10)
C10A	0.0171 (8)	0.0334 (11)	0.0279 (10)	0.0015 (7)	0.0014 (7)	−0.0044 (8)
O3B	0.024 (2)	0.050 (3)	0.204 (9)	−0.0125 (18)	0.035 (4)	−0.065 (4)
C9B	0.0188 (9)	0.0314 (12)	0.0486 (17)	−0.0025 (8)	0.0096 (11)	−0.0163 (12)
C10B	0.0182 (9)	0.0401 (13)	0.0380 (12)	0.0013 (8)	0.0063 (8)	−0.0151 (10)
C11	0.0167 (3)	0.0129 (3)	0.0143 (3)	0.0010 (3)	0.0051 (3)	−0.0006 (3)
C12	0.0261 (4)	0.0140 (3)	0.0201 (4)	0.0012 (3)	0.0119 (3)	0.0001 (3)
C13	0.0427 (7)	0.0260 (5)	0.0786 (10)	−0.0036 (5)	0.0409 (7)	0.0095 (6)
C14	0.0189 (4)	0.0166 (4)	0.0173 (4)	−0.0010 (3)	0.0060 (3)	−0.0042 (3)
C15	0.0282 (4)	0.0160 (4)	0.0318 (5)	−0.0007 (3)	0.0152 (4)	−0.0060 (3)
C16	0.0175 (4)	0.0238 (4)	0.0207 (4)	0.0022 (3)	0.0021 (3)	−0.0036 (3)

O1—C7	1.4095 (11)	C7—C8	1.5533 (12)
O1—H1O1	0.875 (18)	C7—C11	1.5695 (12)
O2—C8	1.2070 (11)	O3A—C9A	1.250 (8)
O4—C12	1.2013 (11)	C9A—C10A	1.496 (3)
O5—C12	1.3416 (12)	C10A—H10A	0.9600
O5—C13	1.4514 (13)	C10A—H10B	0.9600
O6—C14	1.2336 (12)	C10A—H10C	0.9600
N1—C9A	1.386 (2)	O3B—C9B	1.156 (9)
N1—C8	1.4074 (13)	C9B—C10B	1.488 (3)
N1—C1	1.4295 (12)	C10B—H10D	0.9600
N1—C9B	1.498 (3)	C10B—H10E	0.9600
N2—C14	1.3404 (11)	C10B—H10F	0.9600
N2—C11	1.4639 (11)	C11—C16	1.5298 (12)
N2—H1N2	0.888 (17)	C11—C12	1.5379 (12)
C1—C2	1.3890 (12)	C13—H13A	0.9600
C1—C6	1.3952 (12)	C13—H13B	0.9600
C2—C3	1.3944 (14)	C13—H13C	0.9600
C2—H2A	0.9300	C14—C15	1.5025 (13)
C3—C4	1.3904 (14)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.3962 (13)	C15—H15C	0.9600
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.3871 (12)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.5109 (11)
C7—O1—H1O1	111.9 (12)	N1—C9A—C10A	120.17 (19)
C12—O5—C13	114.94 (9)	O3B—C9B—C10B	124.2 (4)
C9A—N1—C8	123.92 (13)	O3B—C9B—N1	117.2 (4)
C9A—N1—C1	124.67 (12)	C10B—C9B—N1	118.4 (2)
C8—N1—C1	109.55 (8)	C9B—C10B—H10D	109.5
C9A—N1—C9B	28.89 (14)	C9B—C10B—H10E	109.5
C8—N1—C9B	125.78 (12)	H10D—C10B—H10E	109.5
C1—N1—C9B	121.41 (14)	C9B—C10B—H10F	109.5
C14—N2—C11	122.41 (7)	H10D—C10B—H10F	109.5
C14—N2—H1N2	119.8 (11)	H10E—C10B—H10F	109.5
C11—N2—H1N2	117.5 (11)	N2—C11—C16	109.79 (7)
C2—C1—C6	121.84 (8)	N2—C11—C12	110.88 (7)
C2—C1—N1	128.31 (9)	C16—C11—C12	109.35 (7)
C6—C1—N1	109.69 (8)	N2—C11—C7	106.85 (7)
C1—C2—C3	117.32 (9)	C16—C11—C7	110.62 (7)
C1—C2—H2A	121.3	C12—C11—C7	109.33 (7)
C3—C2—H2A	121.3	O4—C12—O5	124.52 (9)
C4—C3—C2	121.60 (9)	O4—C12—C11	124.03 (9)
C4—C3—H3A	119.2	O5—C12—C11	111.30 (7)
C2—C3—H3A	119.2	O5—C13—H13A	109.5
C3—C4—C5	120.25 (9)	O5—C13—H13B	109.5
C3—C4—H4A	119.9	H13A—C13—H13B	109.5
C5—C4—H4A	119.9	O5—C13—H13C	109.5
C6—C5—C4	118.84 (9)	H13A—C13—H13C	109.5
C6—C5—H5A	120.6	H13B—C13—H13C	109.5
C4—C5—H5A	120.6	O6—C14—N2	120.42 (8)
C5—C6—C1	120.13 (8)	O6—C14—C15	122.31 (9)
C5—C6—C7	129.64 (8)	N2—C14—C15	117.26 (8)
C1—C6—C7	110.08 (7)	C14—C15—H15A	109.5
O1—C7—C6	115.36 (7)	C14—C15—H15B	109.5
O1—C7—C8	109.87 (7)	H15A—C15—H15B	109.5
C6—C7—C8	101.52 (7)	C14—C15—H15C	109.5
O1—C7—C11	105.03 (7)	H15A—C15—H15C	109.5
C6—C7—C11	113.98 (7)	H15B—C15—H15C	109.5
C8—C7—C11	111.19 (7)	C11—C16—H16A	109.5
O2—C8—N1	126.58 (9)	C11—C16—H16B	109.5
O2—C8—C7	125.27 (9)	H16A—C16—H16B	109.5
N1—C8—C7	108.05 (7)	C11—C16—H16C	109.5
O3A—C9A—N1	118.0 (4)	H16A—C16—H16C	109.5
O3A—C9A—C10A	121.2 (4)	H16B—C16—H16C	109.5
C9A—N1—C1—C2	−5.6 (3)	C8—N1—C9A—O3A	−173.0 (6)
C8—N1—C1—C2	−170.47 (10)	C1—N1—C9A—O3A	24.2 (7)
C9B—N1—C1—C2	28.8 (2)	C9B—N1—C9A—O3A	−69.1 (6)
C9A—N1—C1—C6	169.8 (2)	C8—N1—C9A—C10A	−2.2 (4)
C8—N1—C1—C6	4.91 (12)	C1—N1—C9A—C10A	−165.0 (2)
C9B—N1—C1—C6	−155.78 (19)	C9B—N1—C9A—C10A	101.7 (4)
C6—C1—C2—C3	−1.38 (14)	C9A—N1—C9B—O3B	82.3 (7)
N1—C1—C2—C3	173.51 (10)	C8—N1—C9B—O3B	179.1 (6)
C1—C2—C3—C4	0.06 (14)	C1—N1—C9B—O3B	−23.5 (7)
C2—C3—C4—C5	0.73 (15)	C9A—N1—C9B—C10B	−92.8 (5)
C3—C4—C5—C6	−0.20 (14)	C8—N1—C9B—C10B	4.0 (4)
C4—C5—C6—C1	−1.09 (13)	C1—N1—C9B—C10B	161.4 (2)
C4—C5—C6—C7	−176.31 (9)	C14—N2—C11—C16	−75.49 (10)
C2—C1—C6—C5	1.93 (14)	C14—N2—C11—C12	45.45 (11)
N1—C1—C6—C5	−173.81 (9)	C14—N2—C11—C7	164.50 (8)
C2—C1—C6—C7	178.01 (8)	O1—C7—C11—N2	60.42 (8)
N1—C1—C6—C7	2.27 (11)	C6—C7—C11—N2	−172.37 (7)
C5—C6—C7—O1	49.26 (12)	C8—C7—C11—N2	−58.36 (9)
C1—C6—C7—O1	−126.33 (8)	O1—C7—C11—C16	−59.04 (9)
C5—C6—C7—C8	167.97 (9)	C6—C7—C11—C16	68.17 (9)
C1—C6—C7—C8	−7.62 (9)	C8—C7—C11—C16	−177.83 (7)
C5—C6—C7—C11	−72.40 (12)	O1—C7—C11—C12	−179.52 (7)
C1—C6—C7—C11	112.01 (8)	C6—C7—C11—C12	−52.31 (9)
C9A—N1—C8—O2	1.6 (3)	C8—C7—C11—C12	61.69 (9)
C1—N1—C8—O2	166.66 (10)	C13—O5—C12—O4	3.57 (15)
C9B—N1—C8—O2	−33.7 (3)	C13—O5—C12—C11	179.33 (9)
C9A—N1—C8—C7	−174.8 (2)	N2—C11—C12—O4	−135.23 (9)
C1—N1—C8—C7	−9.79 (12)	C16—C11—C12—O4	−14.03 (12)
C9B—N1—C8—C7	149.9 (2)	C7—C11—C12—O4	107.22 (10)
O1—C7—C8—O2	−43.51 (12)	N2—C11—C12—O5	48.98 (10)
C6—C7—C8—O2	−166.08 (10)	C16—C11—C12—O5	170.18 (7)
C11—C7—C8—O2	72.33 (12)	C7—C11—C12—O5	−68.56 (9)
O1—C7—C8—N1	133.01 (9)	C11—N2—C14—O6	−5.74 (14)
C6—C7—C8—N1	10.43 (10)	C11—N2—C14—C15	175.23 (8)
C11—C7—C8—N1	−111.16 (9)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O6i	0.875 (17)	1.769 (17)	2.6391 (10)	172 (2)
C3—H3A···O1ii	0.93	2.58	3.4098 (12)	150
C15—H15C···Cg1iii	0.96	2.96	3.9104 (11)	169

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O6i	0.875 (17)	1.769 (17)	2.6391 (10)	172 (2)
C3—H3A⋯O1ii	0.93	2.58	3.4098 (12)	150
C15—H15C⋯Cg1iii	0.96	2.96	3.9104 (11)	169

Symmetry codes: (i) ; (ii) ; (iii) .