3-(3-Chloro-3-methyl-1,2,3,4-tetra­hydro­carbazole-2-yl)­propane­nitrile

In the structure of the title compound, C₁₆H₁₇ClN₂, all the bond lengths and angles have normal values. The aromatic indole ring is planar.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.107
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

   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
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-(3-chloro-3-methyl-1,2,3,4-tetrahydrocarbazole-2-yl)-propanenitrile

Crystal data

C16H17ClN2	F(000) = 576
Mr = 272.77	Dx = 1.298 Mg m^−3
Monoclinic, P21/c	Melting point: 413.2-415.2 K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.810 (3) Å	Cell parameters from 25 reflections
b = 7.94 (1) Å	θ = 10.0–13.4°
c = 12.049 (2) Å	µ = 0.26 mm^−1
β = 99.99 (10)°	T = 293 K
V = 1395.4 (18) Å^3	Plate, colorless
Z = 4	0.40 × 0.25 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1499 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 25.2°, θmin = 1.4°
ω/2θ scans	h = −17→17
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = −9→1
Tmin = 0.925, Tmax = 0.979	l = −14→0
3055 measured reflections	3 standard reflections every 3600 min
2512 independent reflections	intensity decay: 1.0%

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 0.3507P] where P = (Fo^2 + 2Fc^2)/3
2512 reflections	(Δ/σ)max = 0.001
189 parameters	Δρmax = 0.19 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
Cl1	0.70078 (4)	0.88302 (8)	0.28431 (5)	0.0535 (2)
N1	0.92705 (13)	0.4966 (3)	0.27745 (16)	0.0479 (5)
H1	0.9234	0.4223	0.2249	0.068 (9)*
N2	0.5920 (2)	0.2558 (4)	0.5467 (3)	0.0972 (10)
C5	1.05238 (16)	0.7769 (3)	0.4769 (2)	0.0458 (6)
H5	1.0395	0.8506	0.5321	0.049 (7)*
C6	1.14125 (16)	0.7554 (3)	0.4597 (2)	0.0511 (6)
H6	1.1882	0.8151	0.5041	0.054 (7)*
C7	1.16243 (16)	0.6462 (3)	0.3771 (2)	0.0506 (6)
H7	1.2229	0.6359	0.3665	0.053 (7)*
C8	1.09523 (16)	0.5538 (3)	0.3116 (2)	0.0485 (6)
H8	1.1092	0.4800	0.2571	0.044 (7)*
C8A	1.00607 (15)	0.5740 (3)	0.32908 (19)	0.0413 (5)
C4B	0.98198 (15)	0.6865 (3)	0.41045 (18)	0.0383 (5)
C4A	0.88471 (15)	0.6745 (3)	0.40307 (18)	0.0392 (5)
C9A	0.85473 (15)	0.5570 (3)	0.32332 (19)	0.0422 (6)
C4	0.82113 (15)	0.7654 (3)	0.46547 (18)	0.0420 (6)
H4A	0.8373	0.8840	0.4699	0.053 (7)*
H4B	0.8288	0.7220	0.5417	0.044 (6)*
C3	0.72061 (15)	0.7473 (3)	0.40988 (18)	0.0399 (5)
C2	0.69881 (14)	0.5650 (3)	0.37255 (19)	0.0415 (6)
H2	0.7143	0.4958	0.4406	0.041 (6)*
C1	0.75884 (16)	0.5001 (3)	0.2904 (2)	0.0491 (6)
H1A	0.7570	0.3780	0.2887	0.060 (7)*
H1B	0.7347	0.5408	0.2152	0.058 (7)*
C13	0.65907 (18)	0.8162 (4)	0.4875 (2)	0.0553 (7)
H13A	0.6594	0.7406	0.5497	0.078 (9)*
H13B	0.5977	0.8270	0.4466	0.063 (8)*
H13C	0.6811	0.9246	0.5152	0.061 (8)*
C10	0.59750 (16)	0.5304 (3)	0.3262 (2)	0.0539 (7)
H10A	0.5600	0.5997	0.3666	0.058 (7)*
H10B	0.5844	0.5630	0.2474	0.059 (8)*
C11	0.57109 (19)	0.3451 (3)	0.3373 (3)	0.0630 (8)
H11A	0.5076	0.3295	0.3020	0.079 (9)*
H11B	0.6088	0.2751	0.2978	0.066 (8)*
C12	0.58249 (18)	0.2921 (4)	0.4548 (3)	0.0650 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0617 (4)	0.0474 (4)	0.0509 (4)	0.0045 (3)	0.0079 (3)	0.0126 (3)
N1	0.0471 (12)	0.0470 (12)	0.0487 (11)	0.0009 (10)	0.0058 (9)	−0.0145 (10)
N2	0.0775 (19)	0.108 (3)	0.110 (2)	−0.0061 (17)	0.0272 (17)	0.034 (2)
C5	0.0520 (15)	0.0315 (13)	0.0503 (13)	0.0019 (11)	−0.0010 (11)	0.0008 (11)
C6	0.0423 (14)	0.0374 (14)	0.0675 (16)	−0.0020 (12)	−0.0076 (12)	0.0088 (13)
C7	0.0423 (13)	0.0440 (15)	0.0645 (16)	0.0073 (11)	0.0066 (12)	0.0143 (13)
C8	0.0491 (14)	0.0456 (14)	0.0509 (14)	0.0103 (12)	0.0093 (11)	0.0018 (12)
C8A	0.0427 (12)	0.0380 (13)	0.0418 (12)	0.0023 (11)	0.0038 (10)	0.0023 (10)
C4B	0.0426 (13)	0.0286 (11)	0.0418 (12)	0.0023 (10)	0.0018 (10)	0.0030 (10)
C4A	0.0424 (13)	0.0320 (12)	0.0412 (12)	0.0008 (10)	0.0024 (10)	−0.0004 (10)
C9A	0.0427 (13)	0.0373 (13)	0.0455 (13)	0.0018 (10)	0.0048 (10)	−0.0044 (10)
C4	0.0489 (14)	0.0326 (12)	0.0433 (13)	0.0003 (11)	0.0046 (10)	−0.0047 (10)
C3	0.0455 (13)	0.0367 (12)	0.0374 (11)	0.0063 (10)	0.0073 (10)	0.0050 (10)
C2	0.0405 (12)	0.0370 (13)	0.0450 (13)	−0.0012 (10)	0.0016 (10)	0.0040 (11)
C1	0.0472 (14)	0.0416 (14)	0.0564 (15)	−0.0003 (12)	0.0028 (11)	−0.0093 (12)
C13	0.0561 (17)	0.0601 (17)	0.0515 (15)	0.0033 (13)	0.0143 (13)	−0.0046 (14)
C10	0.0445 (14)	0.0526 (16)	0.0616 (17)	0.0009 (12)	0.0006 (12)	−0.0001 (14)
C11	0.0466 (15)	0.0587 (18)	0.082 (2)	−0.0121 (14)	0.0074 (14)	−0.0149 (16)
C12	0.0426 (15)	0.0583 (18)	0.097 (2)	−0.0096 (13)	0.0203 (16)	0.0054 (18)

Geometric parameters (Å, º)

Cl1—C3	1.839 (2)	C4—C3	1.530 (3)
N1—C8A	1.372 (3)	C4—H4A	0.9708
N1—C9A	1.374 (3)	C4—H4B	0.9693
N1—H1	0.8603	C3—C13	1.517 (3)
N2—C12	1.130 (4)	C3—C2	1.534 (3)
C5—C6	1.378 (3)	C2—C1	1.530 (3)
C5—C4B	1.398 (3)	C2—C10	1.532 (3)
C5—H5	0.9303	C2—H2	0.9801
C6—C7	1.396 (4)	C1—H1A	0.9700
C6—H6	0.9306	C1—H1B	0.9699
C7—C8	1.371 (3)	C13—H13A	0.9596
C7—H7	0.9303	C13—H13B	0.9596
C8—C8A	1.382 (3)	C13—H13C	0.9596
C8—H8	0.9298	C10—C11	1.534 (4)
C8A—C4B	1.417 (3)	C10—H10A	0.9703
C4B—C4A	1.431 (3)	C10—H10B	0.9707
C4A—C9A	1.357 (3)	C11—C12	1.458 (5)
C4A—C4	1.489 (3)	C11—H11A	0.9700
C9A—C1	1.478 (3)	C11—H11B	0.9696
C8A—N1—C9A	108.94 (19)	C4—C3—C2	110.87 (18)
C8A—N1—H1	125.5	C13—C3—Cl1	105.60 (16)
C9A—N1—H1	125.6	C4—C3—Cl1	108.05 (16)
C6—C5—C4B	119.1 (2)	C2—C3—Cl1	108.44 (15)
C6—C5—H5	120.4	C1—C2—C10	110.25 (19)
C4B—C5—H5	120.5	C1—C2—C3	113.02 (19)
C5—C6—C7	121.5 (2)	C10—C2—C3	114.76 (19)
C5—C6—H6	119.3	C1—C2—H2	105.9
C7—C6—H6	119.2	C10—C2—H2	106.1
C8—C7—C6	120.8 (2)	C3—C2—H2	106.1
C8—C7—H7	119.6	C9A—C1—C2	111.26 (19)
C6—C7—H7	119.6	C9A—C1—H1A	109.5
C7—C8—C8A	117.9 (2)	C2—C1—H1A	109.5
C7—C8—H8	121.0	C9A—C1—H1B	109.3
C8A—C8—H8	121.1	C2—C1—H1B	109.3
N1—C8A—C8	129.9 (2)	H1A—C1—H1B	108.0
N1—C8A—C4B	107.38 (19)	C3—C13—H13A	109.5
C8—C8A—C4B	122.7 (2)	C3—C13—H13B	109.4
C5—C4B—C8A	117.9 (2)	H13A—C13—H13B	109.5
C5—C4B—C4A	135.4 (2)	C3—C13—H13C	109.5
C8A—C4B—C4A	106.66 (19)	H13A—C13—H13C	109.5
C9A—C4A—C4B	107.0 (2)	H13B—C13—H13C	109.5
C9A—C4A—C4	122.2 (2)	C2—C10—C11	112.9 (2)
C4B—C4A—C4	130.9 (2)	C2—C10—H10A	109.0
C4A—C9A—N1	110.0 (2)	C11—C10—H10A	108.9
C4A—C9A—C1	125.6 (2)	C2—C10—H10B	109.0
N1—C9A—C1	124.4 (2)	C11—C10—H10B	109.3
C4A—C4—C3	112.71 (18)	H10A—C10—H10B	107.8
C4A—C4—H4A	109.1	C12—C11—C10	111.9 (2)
C3—C4—H4A	109.1	C12—C11—H11A	109.2
C4A—C4—H4B	109.0	C10—C11—H11A	109.1
C3—C4—H4B	109.1	C12—C11—H11B	109.3
H4A—C4—H4B	107.8	C10—C11—H11B	109.2
C13—C3—C4	109.85 (19)	H11A—C11—H11B	108.0
C13—C3—C2	113.8 (2)	N2—C12—C11	177.9 (4)
C4B—C5—C6—C7	0.4 (4)	C8A—N1—C9A—C4A	0.9 (3)
C5—C6—C7—C8	−1.3 (4)	C8A—N1—C9A—C1	−178.7 (2)
C6—C7—C8—C8A	0.8 (4)	C9A—C4A—C4—C3	−15.1 (3)
C9A—N1—C8A—C8	179.7 (2)	C4B—C4A—C4—C3	164.9 (2)
C9A—N1—C8A—C4B	0.2 (3)	C4A—C4—C3—C13	170.2 (2)
C7—C8—C8A—N1	−178.9 (2)	C4A—C4—C3—C2	43.7 (3)
C7—C8—C8A—C4B	0.6 (3)	C4A—C4—C3—Cl1	−75.0 (2)
C6—C5—C4B—C8A	1.0 (3)	C13—C3—C2—C1	177.6 (2)
C6—C5—C4B—C4A	179.9 (2)	C4—C3—C2—C1	−58.0 (2)
N1—C8A—C4B—C5	178.1 (2)	Cl1—C3—C2—C1	60.4 (2)
C8—C8A—C4B—C5	−1.5 (3)	C13—C3—C2—C10	50.0 (3)
N1—C8A—C4B—C4A	−1.1 (2)	C4—C3—C2—C10	174.3 (2)
C8—C8A—C4B—C4A	179.3 (2)	Cl1—C3—C2—C10	−67.2 (2)
C5—C4B—C4A—C9A	−177.4 (3)	C4A—C9A—C1—C2	−10.8 (3)
C8A—C4B—C4A—C9A	1.6 (2)	N1—C9A—C1—C2	168.7 (2)
C5—C4B—C4A—C4	2.6 (4)	C10—C2—C1—C9A	170.4 (2)
C8A—C4B—C4A—C4	−178.4 (2)	C3—C2—C1—C9A	40.4 (3)
C4B—C4A—C9A—N1	−1.5 (3)	C1—C2—C10—C11	75.6 (3)
C4—C4A—C9A—N1	178.5 (2)	C3—C2—C10—C11	−155.4 (2)
C4B—C4A—C9A—C1	178.0 (2)	C2—C10—C11—C12	63.0 (3)
C4—C4A—C9A—C1	−2.0 (4)