(1S,3aS,4S,7aS)-Ethyl 1-benzyl-2-(4-meth-oxy-benz-yl)-6,7-dimethyl-3-oxo-2,3,3a,4,5,7a-hexa-hydro-1H-isoindole-4-carboxyl-ate dichloro-methane monosolvate.

In the title compound, C(28)H(33)NO(4)·CH(2)Cl(2), the pyrrolidone ring adopts a twisted envelope conformation and the cyclo-hexene has a half-chair conformation. In the crystal, weak C-H⋯O hydrogen bonds link the components into chains along [100].

Related literature

For isoindolin-1-one derivatives in cytochalasins, see: Liu et al. (2006 ▶); Cox et al. (1983 ▶).

Experimental

Crystal data

C28H33NO4·CH2Cl2

M = 532.48

Monoclinic,

a = 9.6864 (5) Å

b = 15.5706 (8) Å

c = 9.7460 (6) Å

β = 109.221 (7)°

V = 1387.99 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.32 × 0.26 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2011 ▶) T min = 0.919, T max = 0.941

6260 measured reflections

3844 independent reflections

2990 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.127

S = 1.07

3844 reflections

330 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1789 Friedel pairs

Flack parameter: −0.05 (11)

Data collection: CrysAlis PRO (Oxford Diffraction, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813002560/cv5380sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002560/cv5380Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002560/cv5380Isup3.cml

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

C28H33NO4·CH2Cl2	F(000) = 564
Mr = 532.48	Dx = 1.274 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2239 reflections
a = 9.6864 (5) Å	θ = 2.9–29.1°
b = 15.5706 (8) Å	µ = 0.27 mm−1
c = 9.7460 (6) Å	T = 293 K
β = 109.221 (7)°	Block, colourless
V = 1387.99 (14) Å3	0.32 × 0.26 × 0.23 mm
Z = 2

Oxford Diffraction Xcalibur (Atlas, Gemini ultra) diffractometer	3844 independent reflections
Radiation source: fine-focus sealed tube	2990 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 10.3592 pixels mm-1	θmax = 25.4°, θmin = 2.9°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2011)	k = −18→14
Tmin = 0.919, Tmax = 0.941	l = −11→11
6260 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.5082P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.127	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.26 e Å−3
3844 reflections	Δρmin = −0.22 e Å−3
330 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0155 (19)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1789 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.05 (11)

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
Cl1	0.9553 (2)	0.0250 (2)	1.0097 (3)	0.1866 (12)
Cl2	0.65374 (18)	0.04546 (13)	0.85047 (17)	0.1164 (6)
O1	1.3771 (3)	−0.2369 (2)	0.9604 (3)	0.0767 (10)
O2	0.8238 (3)	−0.02886 (19)	0.3287 (3)	0.0632 (8)
O3	0.5215 (3)	0.0189 (2)	0.4345 (4)	0.0860 (11)
O4	0.5046 (3)	0.0707 (2)	0.2171 (3)	0.0750 (9)
N1	1.0380 (3)	0.0314 (2)	0.4734 (3)	0.0468 (7)
C1	1.5287 (6)	−0.2472 (4)	1.0238 (6)	0.0980 (19)
H1A	1.5670	−0.2747	0.9558	0.147*
H1C	1.5490	−0.2820	1.1095	0.147*
H1B	1.5738	−0.1920	1.0495	0.147*
C2	1.3277 (4)	−0.1863 (3)	0.8388 (4)	0.0495 (9)
C3	1.1780 (4)	−0.1758 (3)	0.7830 (4)	0.0560 (10)
H3	1.1186	−0.2016	0.8291	0.067*
C4	1.1162 (4)	−0.1279 (3)	0.6604 (4)	0.0528 (10)
H4	1.0151	−0.1221	0.6234	0.063*
C5	1.2028 (4)	−0.0879 (2)	0.5907 (4)	0.0446 (9)
C6	1.3511 (4)	−0.0988 (3)	0.6482 (4)	0.0497 (10)
H6	1.4107	−0.0726	0.6028	0.060*
C7	1.4150 (4)	−0.1476 (3)	0.7712 (4)	0.0540 (10)
H7	1.5160	−0.1540	0.8077	0.065*
C8	1.1352 (4)	−0.0356 (3)	0.4546 (4)	0.0524 (10)
H8B	1.2124	−0.0094	0.4261	0.063*
H8A	1.0805	−0.0736	0.3768	0.063*
C9	1.0877 (4)	0.0985 (2)	0.5848 (4)	0.0464 (9)
H9	1.1032	0.0723	0.6801	0.056*
C10	1.2300 (4)	0.1407 (3)	0.5864 (5)	0.0587 (11)
H10B	1.2683	0.1730	0.6761	0.070*
H10A	1.2998	0.0956	0.5888	0.070*
C11	1.2230 (4)	0.2007 (3)	0.4609 (5)	0.0541 (10)
C12	1.1740 (4)	0.1739 (3)	0.3175 (5)	0.0594 (11)
H12	1.1423	0.1176	0.2952	0.071*
C13	1.1717 (5)	0.2301 (4)	0.2072 (6)	0.0779 (15)
H13	1.1389	0.2109	0.1116	0.093*
C14	1.2158 (5)	0.3122 (4)	0.2352 (8)	0.0866 (17)
H14	1.2121	0.3493	0.1594	0.104*
C15	1.2661 (5)	0.3406 (3)	0.3754 (8)	0.0840 (17)
H15	1.2977	0.3971	0.3952	0.101*
C16	1.2701 (4)	0.2854 (3)	0.4887 (6)	0.0705 (13)
H16	1.3046	0.3053	0.5839	0.085*
C17	0.9501 (4)	0.1545 (2)	0.5469 (4)	0.0426 (9)
H17	0.9475	0.1889	0.4620	0.051*
C18	0.8293 (4)	0.0886 (2)	0.4960 (4)	0.0455 (9)
H18	0.8208	0.0606	0.5829	0.055*
C19	0.8895 (4)	0.0240 (3)	0.4187 (4)	0.0470 (9)
C20	0.6846 (4)	0.1320 (3)	0.4198 (4)	0.0515 (10)
H20	0.6935	0.1668	0.3394	0.062*
C21	0.6515 (5)	0.1908 (3)	0.5308 (5)	0.0699 (13)
H21B	0.5880	0.2367	0.4785	0.084*
H21A	0.5975	0.1580	0.5809	0.084*
C22	0.7822 (5)	0.2308 (3)	0.6435 (5)	0.0604 (11)
C23	0.9207 (5)	0.2151 (3)	0.6560 (4)	0.0556 (10)
C24	1.0504 (6)	0.2564 (3)	0.7643 (5)	0.0743 (13)
H24B	1.1009	0.2909	0.7143	0.111*
H24C	1.1150	0.2129	0.8197	0.111*
H24A	1.0185	0.2921	0.8284	0.111*
C25	0.7356 (6)	0.2921 (3)	0.7405 (6)	0.0922 (18)
H25B	0.6867	0.3406	0.6845	0.138*
H25C	0.8202	0.3114	0.8176	0.138*
H25A	0.6704	0.2632	0.7809	0.138*
C26	0.5632 (4)	0.0670 (3)	0.3608 (5)	0.0645 (12)
C27	0.3958 (7)	0.0046 (4)	0.1472 (7)	0.105 (2)
H27B	0.4442	−0.0502	0.1491	0.126*
H27A	0.3269	−0.0017	0.1997	0.126*
C28	0.3196 (7)	0.0291 (5)	−0.0004 (7)	0.116 (2)
H28C	0.3869	0.0304	−0.0539	0.173*
H28B	0.2774	0.0850	−0.0020	0.173*
H28A	0.2436	−0.0118	−0.0439	0.173*
C29	0.7904 (7)	0.0628 (5)	1.0126 (7)	0.124 (2)
H29A	0.7983	0.1239	1.0332	0.149*
H29B	0.7654	0.0346	1.0900	0.149*

	U11	U22	U33	U12	U13	U23
Cl1	0.0957 (13)	0.250 (3)	0.191 (2)	−0.0212 (17)	0.0151 (13)	−0.069 (2)
Cl2	0.1087 (11)	0.1250 (14)	0.1006 (11)	−0.0138 (10)	0.0143 (9)	−0.0090 (10)
O1	0.064 (2)	0.099 (3)	0.069 (2)	0.0249 (18)	0.0239 (16)	0.0291 (19)
O2	0.0567 (17)	0.0626 (19)	0.0627 (18)	−0.0058 (15)	0.0091 (14)	−0.0102 (16)
O3	0.0700 (19)	0.094 (3)	0.096 (2)	−0.0166 (19)	0.0301 (18)	0.034 (2)
O4	0.0652 (18)	0.080 (2)	0.072 (2)	−0.0154 (17)	0.0118 (16)	0.0209 (17)
N1	0.0445 (17)	0.0443 (19)	0.0474 (17)	0.0077 (15)	0.0093 (13)	−0.0010 (15)
C1	0.079 (4)	0.128 (5)	0.079 (4)	0.039 (3)	0.016 (3)	0.029 (3)
C2	0.051 (2)	0.048 (2)	0.050 (2)	0.0079 (19)	0.0177 (18)	0.0022 (19)
C3	0.046 (2)	0.056 (3)	0.072 (3)	−0.006 (2)	0.027 (2)	0.002 (2)
C4	0.0315 (18)	0.053 (3)	0.073 (3)	−0.0017 (18)	0.0157 (19)	0.001 (2)
C5	0.047 (2)	0.039 (2)	0.047 (2)	0.0029 (17)	0.0149 (17)	−0.0075 (17)
C6	0.0374 (19)	0.054 (2)	0.062 (2)	−0.0011 (18)	0.0232 (18)	0.000 (2)
C7	0.0333 (18)	0.063 (3)	0.066 (3)	0.0107 (19)	0.0173 (18)	0.001 (2)
C8	0.053 (2)	0.050 (2)	0.053 (2)	0.009 (2)	0.0160 (19)	−0.0016 (19)
C9	0.046 (2)	0.049 (2)	0.038 (2)	0.0094 (18)	0.0060 (16)	−0.0004 (17)
C10	0.043 (2)	0.062 (3)	0.058 (3)	0.005 (2)	−0.0011 (18)	−0.011 (2)
C11	0.0334 (19)	0.054 (3)	0.077 (3)	0.0040 (18)	0.0197 (19)	−0.007 (2)
C12	0.055 (2)	0.059 (3)	0.067 (3)	−0.002 (2)	0.025 (2)	−0.006 (2)
C13	0.072 (3)	0.082 (4)	0.093 (4)	0.009 (3)	0.045 (3)	0.028 (3)
C14	0.064 (3)	0.085 (4)	0.134 (5)	0.019 (3)	0.064 (3)	0.038 (4)
C15	0.059 (3)	0.054 (3)	0.155 (6)	−0.003 (2)	0.057 (3)	0.007 (4)
C16	0.048 (3)	0.057 (3)	0.112 (4)	−0.002 (2)	0.033 (3)	−0.015 (3)
C17	0.048 (2)	0.047 (2)	0.0358 (19)	0.0074 (17)	0.0182 (16)	0.0057 (16)
C18	0.045 (2)	0.052 (2)	0.0399 (19)	0.0053 (18)	0.0133 (16)	0.0107 (17)
C19	0.048 (2)	0.048 (2)	0.0408 (19)	0.003 (2)	0.0095 (17)	0.0096 (19)
C20	0.043 (2)	0.057 (3)	0.057 (2)	0.0073 (19)	0.0209 (19)	0.021 (2)
C21	0.063 (3)	0.069 (3)	0.092 (3)	0.015 (2)	0.044 (3)	0.021 (3)
C22	0.081 (3)	0.051 (3)	0.067 (3)	0.018 (2)	0.048 (2)	0.008 (2)
C23	0.082 (3)	0.044 (2)	0.043 (2)	0.009 (2)	0.023 (2)	0.0101 (19)
C24	0.100 (4)	0.064 (3)	0.058 (3)	0.013 (3)	0.023 (3)	−0.017 (2)
C25	0.124 (4)	0.080 (4)	0.107 (4)	0.017 (3)	0.084 (4)	0.002 (3)
C26	0.043 (2)	0.067 (3)	0.084 (3)	0.004 (2)	0.023 (2)	0.029 (3)
C27	0.102 (4)	0.099 (4)	0.099 (4)	−0.044 (4)	0.013 (3)	0.021 (3)
C28	0.104 (4)	0.119 (5)	0.110 (5)	−0.030 (4)	0.015 (4)	−0.032 (4)
C29	0.132 (5)	0.144 (6)	0.085 (4)	0.014 (5)	0.020 (4)	−0.033 (4)

Cl1—C29	1.712 (7)	C13—C14	1.347 (8)
Cl2—C29	1.716 (6)	C13—H13	0.9300
O1—C2	1.372 (5)	C14—C15	1.364 (7)
O1—C1	1.402 (6)	C14—H14	0.9300
O2—C19	1.218 (4)	C15—C16	1.389 (7)
O3—C26	1.197 (5)	C15—H15	0.9300
O4—C26	1.328 (5)	C16—H16	0.9300
O4—C27	1.470 (6)	C17—C18	1.511 (5)
N1—C19	1.364 (4)	C17—C23	1.517 (5)
N1—C8	1.456 (5)	C17—H17	0.9800
N1—C9	1.470 (5)	C18—C19	1.486 (5)
C1—H1A	0.9600	C18—C20	1.512 (5)
C1—H1C	0.9600	C18—H18	0.9800
C1—H1B	0.9600	C20—C26	1.513 (6)
C2—C7	1.371 (5)	C20—C21	1.531 (6)
C2—C3	1.381 (5)	C20—H20	0.9800
C3—C4	1.368 (5)	C21—C22	1.510 (7)
C3—H3	0.9300	C21—H21B	0.9700
C4—C5	1.389 (5)	C21—H21A	0.9700
C4—H4	0.9300	C22—C23	1.329 (6)
C5—C6	1.369 (5)	C22—C25	1.513 (6)
C5—C8	1.509 (5)	C23—C24	1.495 (6)
C6—C7	1.382 (5)	C24—H24B	0.9600
C6—H6	0.9300	C24—H24C	0.9600
C7—H7	0.9300	C24—H24A	0.9600
C8—H8B	0.9700	C25—H25B	0.9600
C8—H8A	0.9700	C25—H25C	0.9600
C9—C10	1.522 (5)	C25—H25A	0.9600
C9—C17	1.532 (5)	C27—C28	1.435 (8)
C9—H9	0.9800	C27—H27B	0.9700
C10—C11	1.522 (6)	C27—H27A	0.9700
C10—H10B	0.9700	C28—H28C	0.9600
C10—H10A	0.9700	C28—H28B	0.9600
C11—C12	1.385 (6)	C28—H28A	0.9600
C11—C16	1.394 (6)	C29—H29A	0.9700
C12—C13	1.380 (6)	C29—H29B	0.9700
C12—H12	0.9300
C2—O1—C1	117.6 (4)	C18—C17—C9	102.2 (3)
C26—O4—C27	116.8 (4)	C23—C17—C9	122.3 (3)
C19—N1—C8	122.2 (3)	C18—C17—H17	107.0
C19—N1—C9	113.3 (3)	C23—C17—H17	107.0
C8—N1—C9	122.3 (3)	C9—C17—H17	107.0
O1—C1—H1A	109.5	C19—C18—C17	103.6 (3)
O1—C1—H1C	109.5	C19—C18—C20	120.5 (3)
H1A—C1—H1C	109.5	C17—C18—C20	110.6 (3)
O1—C1—H1B	109.5	C19—C18—H18	107.1
H1A—C1—H1B	109.5	C17—C18—H18	107.1
H1C—C1—H1B	109.5	C20—C18—H18	107.1
C7—C2—O1	125.0 (3)	O2—C19—N1	124.8 (4)
C7—C2—C3	119.5 (3)	O2—C19—C18	128.6 (3)
O1—C2—C3	115.5 (3)	N1—C19—C18	106.5 (3)
C4—C3—C2	120.6 (4)	C18—C20—C26	111.6 (3)
C4—C3—H3	119.7	C18—C20—C21	107.2 (3)
C2—C3—H3	119.7	C26—C20—C21	110.6 (3)
C3—C4—C5	120.7 (3)	C18—C20—H20	109.1
C3—C4—H4	119.6	C26—C20—H20	109.1
C5—C4—H4	119.6	C21—C20—H20	109.1
C6—C5—C4	117.7 (3)	C22—C21—C20	116.1 (3)
C6—C5—C8	121.3 (3)	C22—C21—H21B	108.3
C4—C5—C8	120.9 (3)	C20—C21—H21B	108.3
C5—C6—C7	122.2 (3)	C22—C21—H21A	108.3
C5—C6—H6	118.9	C20—C21—H21A	108.3
C7—C6—H6	118.9	H21B—C21—H21A	107.4
C2—C7—C6	119.2 (3)	C23—C22—C21	124.7 (4)
C2—C7—H7	120.4	C23—C22—C25	124.0 (5)
C6—C7—H7	120.4	C21—C22—C25	111.3 (4)
N1—C8—C5	112.8 (3)	C22—C23—C24	125.0 (4)
N1—C8—H8B	109.0	C22—C23—C17	117.8 (4)
C5—C8—H8B	109.0	C24—C23—C17	117.1 (4)
N1—C8—H8A	109.0	C23—C24—H24B	109.5
C5—C8—H8A	109.0	C23—C24—H24C	109.5
H8B—C8—H8A	107.8	H24B—C24—H24C	109.5
N1—C9—C10	113.0 (3)	C23—C24—H24A	109.5
N1—C9—C17	100.3 (3)	H24B—C24—H24A	109.5
C10—C9—C17	118.0 (3)	H24C—C24—H24A	109.5
N1—C9—H9	108.3	C22—C25—H25B	109.5
C10—C9—H9	108.3	C22—C25—H25C	109.5
C17—C9—H9	108.3	H25B—C25—H25C	109.5
C11—C10—C9	117.1 (3)	C22—C25—H25A	109.5
C11—C10—H10B	108.0	H25B—C25—H25A	109.5
C9—C10—H10B	108.0	H25C—C25—H25A	109.5
C11—C10—H10A	108.0	O3—C26—O4	123.2 (4)
C9—C10—H10A	108.0	O3—C26—C20	124.3 (4)
H10B—C10—H10A	107.3	O4—C26—C20	112.4 (4)
C12—C11—C16	117.6 (4)	C28—C27—O4	109.4 (5)
C12—C11—C10	122.4 (4)	C28—C27—H27B	109.8
C16—C11—C10	120.0 (4)	O4—C27—H27B	109.8
C13—C12—C11	120.5 (5)	C28—C27—H27A	109.8
C13—C12—H12	119.8	O4—C27—H27A	109.8
C11—C12—H12	119.8	H27B—C27—H27A	108.2
C14—C13—C12	121.4 (6)	C27—C28—H28C	109.5
C14—C13—H13	119.3	C27—C28—H28B	109.5
C12—C13—H13	119.3	H28C—C28—H28B	109.5
C13—C14—C15	119.7 (5)	C27—C28—H28A	109.5
C13—C14—H14	120.1	H28C—C28—H28A	109.5
C15—C14—H14	120.1	H28B—C28—H28A	109.5
C14—C15—C16	120.2 (5)	Cl1—C29—Cl2	111.8 (4)
C14—C15—H15	119.9	Cl1—C29—H29A	109.3
C16—C15—H15	119.9	Cl2—C29—H29A	109.3
C15—C16—C11	120.6 (5)	Cl1—C29—H29B	109.3
C15—C16—H16	119.7	Cl2—C29—H29B	109.3
C11—C16—H16	119.7	H29A—C29—H29B	107.9
C18—C17—C23	110.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29B···O2i	0.97	2.42	3.313 (7)	153
C6—H6···O3ii	0.93	2.65	3.562 (5)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29B⋯O2i	0.97	2.42	3.313 (7)	153
C6—H6⋯O3ii	0.93	2.65	3.562 (5)	166

Symmetry codes: (i) ; (ii) .