(Z)-[2-(1-Methyl-1H-indol-3-yl)methyl­idene]cyclo­hexa­none

In the title compound, C₁₆H₁₇NO, the cyclo­hexa­none ring adopts an envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.052
• wR factor = 0.141
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

(Z)-[2-(1-Methyl-1H-indol-3-yl)methylidene]cyclohexanone

Crystal data

C16H17NO	F(000) = 1024
Mr = 239.31	Dx = 1.272 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2714 reflections
a = 7.9154 (9) Å	θ = 3.1–22.8°
b = 13.7376 (14) Å	µ = 0.08 mm^−1
c = 22.980 (3) Å	T = 273 K
V = 2498.8 (5) Å^3	Needle, colourless
Z = 8	0.19 × 0.11 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1770 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
ω scans	h = −9→9
11800 measured reflections	k = −15→14
2126 independent reflections	l = −27→25

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0709P)^2 + 0.755P] where P = (Fo^2 + 2Fc^2)/3
2126 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.15 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.

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

	x	y	z	Uiso*/Ueq
O1	0.8217 (3)	0.67411 (14)	−0.02017 (7)	0.0901 (8)
N1	1.0160 (2)	0.62749 (12)	0.24967 (7)	0.0380 (4)
C1	1.0932 (2)	0.54634 (14)	0.22694 (8)	0.0348 (5)
C2	1.1862 (2)	0.47407 (16)	0.25431 (9)	0.0423 (5)
H2	1.2047	0.4752	0.2943	0.051*
C3	1.2498 (3)	0.40080 (17)	0.22022 (9)	0.0471 (6)
H3	1.3141	0.3519	0.2374	0.057*
C4	1.2202 (3)	0.39787 (16)	0.16014 (10)	0.0472 (6)
H4	1.2624	0.3464	0.1383	0.057*
C5	1.1295 (2)	0.47008 (15)	0.13314 (9)	0.0408 (5)
H5	1.1111	0.4681	0.0932	0.049*
C6	1.0651 (2)	0.54654 (14)	0.16639 (8)	0.0343 (5)
C7	0.9700 (2)	0.63318 (15)	0.15292 (8)	0.0357 (5)
C8	0.9433 (2)	0.67827 (15)	0.20550 (8)	0.0382 (5)
H8	0.8835	0.7360	0.2102	0.046*
C9	0.9946 (3)	0.64802 (17)	0.31138 (8)	0.0490 (6)
H9A	0.9423	0.7106	0.3161	0.073*
H9B	1.1030	0.6481	0.3301	0.073*
H9C	0.9244	0.5989	0.3286	0.073*
C10	0.9216 (2)	0.65971 (15)	0.09448 (8)	0.0394 (5)
H10	0.9315	0.6097	0.0674	0.047*
C11	0.8647 (3)	0.74406 (15)	0.07244 (8)	0.0391 (5)
C12	0.8347 (3)	0.83447 (15)	0.10760 (9)	0.0482 (6)
H12A	0.9109	0.8342	0.1407	0.058*
H12B	0.7202	0.8328	0.1226	0.058*
C13	0.8594 (4)	0.92872 (17)	0.07414 (10)	0.0596 (7)
H13A	0.8163	0.9826	0.0970	0.072*
H13B	0.9791	0.9395	0.0678	0.072*
C14	0.7697 (3)	0.92591 (18)	0.01639 (10)	0.0603 (7)
H14A	0.7849	0.9876	−0.0035	0.072*
H14B	0.6497	0.9163	0.0227	0.072*
C15	0.8380 (3)	0.84456 (17)	−0.02102 (9)	0.0550 (6)
H15A	0.7706	0.8402	−0.0562	0.066*
H15B	0.9528	0.8604	−0.0324	0.066*
C16	0.8381 (3)	0.74745 (17)	0.00849 (9)	0.0488 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.175 (2)	0.0523 (13)	0.0432 (10)	0.0157 (12)	−0.0290 (11)	−0.0103 (8)
N1	0.0430 (9)	0.0408 (11)	0.0301 (8)	−0.0010 (8)	−0.0002 (6)	0.0002 (7)
C1	0.0333 (9)	0.0348 (12)	0.0363 (10)	−0.0067 (8)	0.0023 (7)	0.0019 (8)
C2	0.0413 (11)	0.0470 (14)	0.0386 (10)	−0.0050 (9)	−0.0034 (8)	0.0103 (10)
C3	0.0433 (11)	0.0413 (15)	0.0567 (14)	0.0020 (10)	−0.0008 (10)	0.0110 (10)
C4	0.0496 (12)	0.0381 (14)	0.0537 (13)	0.0021 (10)	0.0077 (10)	0.0001 (10)
C5	0.0463 (11)	0.0397 (13)	0.0363 (10)	−0.0032 (9)	0.0034 (8)	−0.0003 (9)
C6	0.0348 (9)	0.0345 (12)	0.0336 (10)	−0.0065 (8)	0.0023 (8)	0.0029 (8)
C7	0.0399 (10)	0.0336 (12)	0.0335 (10)	−0.0018 (9)	0.0002 (8)	0.0018 (8)
C8	0.0405 (10)	0.0347 (12)	0.0394 (11)	0.0013 (9)	0.0000 (8)	0.0020 (9)
C9	0.0523 (12)	0.0599 (16)	0.0346 (11)	−0.0012 (11)	0.0008 (9)	−0.0039 (10)
C10	0.0475 (11)	0.0362 (13)	0.0346 (10)	−0.0016 (9)	0.0007 (8)	−0.0027 (8)
C11	0.0466 (11)	0.0367 (13)	0.0340 (10)	0.0001 (9)	−0.0028 (8)	−0.0003 (8)
C12	0.0657 (14)	0.0418 (14)	0.0370 (11)	0.0034 (11)	−0.0053 (10)	−0.0003 (9)
C13	0.0906 (18)	0.0387 (14)	0.0495 (13)	0.0012 (13)	−0.0122 (12)	0.0022 (10)
C14	0.0866 (18)	0.0438 (16)	0.0504 (13)	0.0071 (13)	−0.0104 (12)	0.0071 (11)
C15	0.0714 (15)	0.0567 (16)	0.0369 (12)	0.0061 (12)	−0.0056 (10)	0.0080 (10)
C16	0.0653 (14)	0.0447 (15)	0.0365 (11)	0.0083 (11)	−0.0073 (10)	−0.0036 (10)

Geometric parameters (Å, º)

O1—C16	1.210 (3)	C9—H9B	0.9600
N1—C8	1.359 (2)	C9—H9C	0.9600
N1—C1	1.374 (2)	C10—C11	1.342 (3)
N1—C9	1.456 (2)	C10—H10	0.9300
C1—C2	1.387 (3)	C11—C16	1.485 (3)
C1—C6	1.409 (3)	C11—C12	1.501 (3)
C2—C3	1.371 (3)	C12—C13	1.518 (3)
C2—H2	0.9300	C12—H12A	0.9700
C3—C4	1.401 (3)	C12—H12B	0.9700
C3—H3	0.9300	C13—C14	1.505 (3)
C4—C5	1.373 (3)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.395 (3)	C14—C15	1.510 (3)
C5—H5	0.9300	C14—H14A	0.9700
C6—C7	1.442 (3)	C14—H14B	0.9700
C7—C8	1.374 (3)	C15—C16	1.497 (3)
C7—C10	1.443 (3)	C15—H15A	0.9700
C8—H8	0.9300	C15—H15B	0.9700
C9—H9A	0.9600
C8—N1—C1	108.70 (16)	C11—C10—C7	131.16 (19)
C8—N1—C9	125.38 (17)	C11—C10—H10	114.4
C1—N1—C9	125.38 (17)	C7—C10—H10	114.4
N1—C1—C2	130.12 (18)	C10—C11—C16	116.61 (18)
N1—C1—C6	107.67 (16)	C10—C11—C12	124.36 (17)
C2—C1—C6	122.21 (18)	C16—C11—C12	118.97 (18)
C3—C2—C1	117.48 (19)	C11—C12—C13	114.38 (18)
C3—C2—H2	121.3	C11—C12—H12A	108.7
C1—C2—H2	121.3	C13—C12—H12A	108.7
C2—C3—C4	121.50 (19)	C11—C12—H12B	108.7
C2—C3—H3	119.3	C13—C12—H12B	108.7
C4—C3—H3	119.3	H12A—C12—H12B	107.6
C5—C4—C3	120.8 (2)	C14—C13—C12	111.3 (2)
C5—C4—H4	119.6	C14—C13—H13A	109.4
C3—C4—H4	119.6	C12—C13—H13A	109.4
C4—C5—C6	119.18 (18)	C14—C13—H13B	109.4
C4—C5—H5	120.4	C12—C13—H13B	109.4
C6—C5—H5	120.4	H13A—C13—H13B	108.0
C5—C6—C1	118.79 (17)	C13—C14—C15	110.6 (2)
C5—C6—C7	134.00 (17)	C13—C14—H14A	109.5
C1—C6—C7	107.21 (16)	C15—C14—H14A	109.5
C8—C7—C6	105.28 (16)	C13—C14—H14B	109.5
C8—C7—C10	131.6 (2)	C15—C14—H14B	109.5
C6—C7—C10	123.14 (17)	H14A—C14—H14B	108.1
N1—C8—C7	111.12 (19)	C16—C15—C14	113.69 (18)
N1—C8—H8	124.4	C16—C15—H15A	108.8
C7—C8—H8	124.4	C14—C15—H15A	108.8
N1—C9—H9A	109.5	C16—C15—H15B	108.8
N1—C9—H9B	109.5	C14—C15—H15B	108.8
H9A—C9—H9B	109.5	H15A—C15—H15B	107.7
N1—C9—H9C	109.5	O1—C16—C11	121.8 (2)
H9A—C9—H9C	109.5	O1—C16—C15	119.70 (18)
H9B—C9—H9C	109.5	C11—C16—C15	118.44 (19)
C8—N1—C1—C2	178.40 (19)	C1—N1—C8—C7	−0.1 (2)
C9—N1—C1—C2	−9.7 (3)	C9—N1—C8—C7	−171.98 (18)
C8—N1—C1—C6	−0.8 (2)	C6—C7—C8—N1	0.9 (2)
C9—N1—C1—C6	171.11 (17)	C10—C7—C8—N1	−178.54 (19)
N1—C1—C2—C3	−179.74 (19)	C8—C7—C10—C11	14.4 (4)
C6—C1—C2—C3	−0.7 (3)	C6—C7—C10—C11	−164.9 (2)
C1—C2—C3—C4	−1.0 (3)	C7—C10—C11—C16	175.8 (2)
C2—C3—C4—C5	1.7 (3)	C7—C10—C11—C12	−1.3 (4)
C3—C4—C5—C6	−0.6 (3)	C10—C11—C12—C13	150.0 (2)
C4—C5—C6—C1	−1.0 (3)	C16—C11—C12—C13	−27.1 (3)
C4—C5—C6—C7	178.5 (2)	C11—C12—C13—C14	47.6 (3)
N1—C1—C6—C5	−179.08 (16)	C12—C13—C14—C15	−60.8 (3)
C2—C1—C6—C5	1.7 (3)	C13—C14—C15—C16	52.8 (3)
N1—C1—C6—C7	1.30 (19)	C10—C11—C16—O1	20.1 (3)
C2—C1—C6—C7	−177.94 (17)	C12—C11—C16—O1	−162.6 (3)
C5—C6—C7—C8	179.1 (2)	C10—C11—C16—C15	−157.7 (2)
C1—C6—C7—C8	−1.3 (2)	C12—C11—C16—C15	19.6 (3)
C5—C6—C7—C10	−1.4 (3)	C14—C15—C16—O1	149.9 (3)
C1—C6—C7—C10	178.17 (17)	C14—C15—C16—C11	−32.3 (3)