(Z)-3-(4-Methoxy­benzyl­idene)-2-methyl­isoindolin-1-one

The title compound, C₁₇H₁₅NO₂, consists of two planar sub-units, viz. a lactam and a 4-methoxy­benzyl moiety. The double bond connecting the sub-units has a Z configuration.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.116
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SCHAKAL 99; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

(Z)-3-(4-Methoxybenzylidene)-2-methylisoindolin-1-one

Crystal data

C17H15NO2	F(000) = 560
Mr = 265.30	Dx = 1.329 Mg m^−3
Monoclinic, P21/n	Melting point: 359 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.9750 (5) Å	Cell parameters from 9520 reflections
b = 14.6856 (7) Å	θ = 2.4–27.0°
c = 10.1388 (5) Å	µ = 0.09 mm^−1
β = 116.812 (2)°	T = 100 K
V = 1325.55 (11) Å^3	Prism, colourless
Z = 4	0.3 × 0.25 × 0.2 mm

Data collection

Nonius KappaCCD diffractometer	2066 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 27.0°, θmin = 2.4°
φ and ω scans	h = −12→11
9520 measured reflections	k = −18→18
2851 independent reflections	l = −12→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0674P)^2] where P = (Fo^2 + 2Fc^2)/3
2851 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.24 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	0.34415 (12)	−0.07655 (6)	0.35686 (11)	0.0369 (3)
O2	0.64622 (12)	0.40689 (6)	0.05818 (12)	0.0362 (3)
N4	0.34164 (13)	0.02214 (7)	0.17732 (12)	0.0269 (3)
C1	0.29473 (16)	−0.05349 (9)	0.22757 (16)	0.0282 (4)
C2	0.25860 (16)	0.03331 (9)	0.02296 (15)	0.0262 (3)
C3	0.15431 (16)	−0.04471 (9)	−0.02793 (16)	0.0266 (3)
C4	0.04925 (17)	−0.07093 (10)	−0.16799 (17)	0.0320 (4)
C5	−0.03180 (17)	−0.15017 (11)	−0.17946 (18)	0.0353 (4)
C6	−0.01060 (18)	−0.20148 (10)	−0.05607 (18)	0.0349 (4)
C7	0.09423 (16)	−0.17484 (10)	0.08346 (18)	0.0324 (4)
C8	0.17659 (16)	−0.09667 (9)	0.09504 (16)	0.0268 (3)
C9	0.44049 (19)	0.08951 (10)	0.28011 (18)	0.0326 (4)
C10	0.26628 (17)	0.10085 (9)	−0.06265 (17)	0.0294 (4)
C11	0.37081 (16)	0.17896 (9)	−0.02341 (15)	0.0282 (3)
C12	0.31491 (18)	0.26835 (10)	−0.04395 (17)	0.0328 (4)
C13	0.40998 (17)	0.34203 (10)	−0.01267 (17)	0.0338 (4)
C14	0.56211 (16)	0.32911 (9)	0.03608 (15)	0.0292 (4)
C15	0.62065 (18)	0.24134 (10)	0.05742 (16)	0.0301 (4)
C16	0.52366 (17)	0.16770 (10)	0.02664 (16)	0.0309 (4)
C17	0.8011 (2)	0.39646 (12)	0.0940 (2)	0.0407 (4)
H4	0.0297 (16)	−0.0365 (10)	−0.2567 (16)	0.030 (4)*
H5	−0.1058 (18)	−0.1698 (10)	−0.2774 (18)	0.043 (5)*
H6	−0.0754 (17)	−0.2532 (11)	−0.0719 (17)	0.041 (4)*
H7	0.1130 (17)	−0.2075 (11)	0.1741 (18)	0.042 (4)*
H9A	0.5394 (19)	0.0954 (10)	0.2755 (17)	0.035 (4)*
H9B	0.4639 (16)	0.0701 (9)	0.3821 (17)	0.030 (4)*
H9C	0.3902 (19)	0.1490 (12)	0.2558 (18)	0.048 (5)*
H10	0.1866 (17)	0.0985 (9)	−0.1634 (17)	0.026 (4)*
H12	0.2027 (17)	0.2779 (10)	−0.0812 (15)	0.031 (4)*
H13	0.3678 (19)	0.4035 (11)	−0.0268 (18)	0.047 (5)*
H15	0.7253 (15)	0.2312 (9)	0.0913 (14)	0.022 (4)*
H16	0.5664 (18)	0.1052 (11)	0.0419 (18)	0.044 (5)*
H17A	0.8156 (18)	0.3551 (11)	0.0199 (19)	0.048 (5)*
H17B	0.8615 (18)	0.3704 (10)	0.1930 (19)	0.041 (5)*
H17C	0.8422 (18)	0.4596 (12)	0.0955 (18)	0.053 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0464 (7)	0.0287 (6)	0.0303 (6)	−0.0022 (5)	0.0125 (5)	0.0059 (4)
O2	0.0374 (7)	0.0250 (6)	0.0486 (7)	−0.0043 (5)	0.0216 (5)	−0.0024 (4)
N4	0.0333 (7)	0.0175 (6)	0.0286 (7)	0.0004 (5)	0.0129 (5)	0.0003 (5)
C1	0.0329 (8)	0.0190 (7)	0.0331 (9)	0.0029 (6)	0.0152 (7)	0.0020 (6)
C2	0.0294 (8)	0.0202 (7)	0.0291 (8)	0.0041 (6)	0.0131 (6)	−0.0003 (6)
C3	0.0279 (8)	0.0215 (7)	0.0329 (8)	0.0041 (6)	0.0158 (6)	−0.0009 (6)
C4	0.0344 (9)	0.0313 (8)	0.0312 (9)	0.0017 (6)	0.0157 (7)	0.0000 (7)
C5	0.0309 (8)	0.0365 (9)	0.0375 (9)	−0.0041 (7)	0.0147 (7)	−0.0102 (7)
C6	0.0348 (9)	0.0271 (8)	0.0466 (10)	−0.0064 (7)	0.0217 (8)	−0.0071 (7)
C7	0.0369 (9)	0.0233 (8)	0.0397 (9)	−0.0004 (6)	0.0198 (8)	0.0008 (6)
C8	0.0309 (8)	0.0177 (7)	0.0337 (8)	0.0032 (6)	0.0163 (6)	−0.0002 (6)
C9	0.0422 (10)	0.0208 (8)	0.0311 (9)	−0.0026 (7)	0.0132 (7)	−0.0025 (6)
C10	0.0318 (8)	0.0250 (8)	0.0304 (8)	0.0026 (6)	0.0132 (7)	0.0031 (6)
C11	0.0352 (8)	0.0244 (7)	0.0282 (8)	0.0016 (6)	0.0171 (7)	0.0053 (6)
C12	0.0335 (9)	0.0269 (8)	0.0396 (9)	0.0032 (7)	0.0179 (7)	0.0066 (7)
C13	0.0393 (9)	0.0224 (8)	0.0439 (9)	0.0050 (7)	0.0224 (7)	0.0056 (6)
C14	0.0367 (9)	0.0231 (8)	0.0300 (8)	−0.0035 (6)	0.0171 (7)	0.0006 (6)
C15	0.0304 (9)	0.0292 (8)	0.0323 (8)	0.0042 (7)	0.0157 (7)	0.0035 (6)
C16	0.0355 (9)	0.0225 (8)	0.0356 (9)	0.0025 (6)	0.0170 (7)	0.0043 (6)
C17	0.0403 (10)	0.0348 (10)	0.0482 (12)	−0.0067 (8)	0.0209 (9)	−0.0032 (8)

Geometric parameters (Å, º)

O1—C1	1.2219 (16)	C9—H9A	1.012 (17)
O2—C14	1.3744 (16)	C9—H9B	0.994 (15)
O2—C17	1.426 (2)	C9—H9C	0.982 (18)
N4—C1	1.3883 (18)	C10—C11	1.4789 (19)
N4—C2	1.4117 (17)	C10—H10	0.971 (15)
N4—C9	1.4527 (18)	C11—C16	1.383 (2)
C1—C8	1.472 (2)	C11—C12	1.4046 (19)
C2—C10	1.343 (2)	C12—C13	1.378 (2)
C2—C3	1.4754 (19)	C12—H12	1.017 (15)
C3—C4	1.386 (2)	C13—C14	1.381 (2)
C3—C8	1.3915 (19)	C13—H13	0.979 (16)
C4—C5	1.392 (2)	C14—C15	1.3911 (19)
C4—H4	0.972 (15)	C15—C16	1.389 (2)
C5—C6	1.392 (2)	C15—H15	0.952 (13)
C5—H5	0.976 (15)	C16—H16	0.995 (16)
C6—C7	1.383 (2)	C17—H17A	1.026 (17)
C6—H6	0.962 (16)	C17—H17B	0.986 (17)
C7—C8	1.3855 (19)	C17—H17C	1.011 (18)
C7—H7	0.977 (17)
C14—O2—C17	117.61 (12)	N4—C9—H9C	108.8 (10)
C1—N4—C2	111.93 (11)	H9A—C9—H9C	108.1 (13)
C1—N4—C9	120.91 (12)	H9B—C9—H9C	111.7 (12)
C2—N4—C9	125.82 (12)	C2—C10—C11	129.64 (14)
O1—C1—N4	125.15 (13)	C2—C10—H10	113.3 (8)
O1—C1—C8	129.00 (13)	C11—C10—H10	117.0 (8)
N4—C1—C8	105.85 (12)	C16—C11—C12	117.68 (13)
C10—C2—N4	128.79 (13)	C16—C11—C10	122.20 (13)
C10—C2—C3	125.75 (13)	C12—C11—C10	120.04 (13)
N4—C2—C3	105.43 (11)	C13—C12—C11	120.91 (14)
C4—C3—C8	120.47 (13)	C13—C12—H12	120.3 (8)
C4—C3—C2	131.47 (13)	C11—C12—H12	118.7 (8)
C8—C3—C2	108.06 (12)	C12—C13—C14	120.37 (14)
C3—C4—C5	117.41 (14)	C12—C13—H13	119.0 (10)
C3—C4—H4	123.2 (9)	C14—C13—H13	120.6 (10)
C5—C4—H4	119.4 (9)	O2—C14—C13	115.83 (12)
C4—C5—C6	122.03 (14)	O2—C14—C15	124.20 (13)
C4—C5—H5	118.5 (9)	C13—C14—C15	119.96 (13)
C6—C5—H5	119.5 (9)	C16—C15—C14	119.04 (14)
C7—C6—C5	120.28 (15)	C16—C15—H15	119.9 (8)
C7—C6—H6	122.3 (9)	C14—C15—H15	121.0 (8)
C5—C6—H6	117.3 (9)	C11—C16—C15	122.02 (13)
C6—C7—C8	117.83 (14)	C11—C16—H16	119.4 (9)
C6—C7—H7	124.0 (9)	C15—C16—H16	118.5 (9)
C8—C7—H7	118.2 (9)	O2—C17—H17A	111.8 (9)
C7—C8—C3	121.98 (13)	O2—C17—H17B	113.3 (10)
C7—C8—C1	129.35 (13)	H17A—C17—H17B	107.0 (13)
C3—C8—C1	108.67 (12)	O2—C17—H17C	106.9 (10)
N4—C9—H9A	112.7 (9)	H17A—C17—H17C	111.3 (13)
N4—C9—H9B	108.4 (8)	H17B—C17—H17C	106.4 (13)
H9A—C9—H9B	107.2 (12)