Methyl 5-chloro-1H-indole-2-carboxyl­ate

In the mol­ecule of the title compound, C₁₀H₈ClNO₂, the indole ring system is planar. In the crystal structure, the mol­ecules are linked by inter­molecular N—H...O hydrogen bonds, forming centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.118
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.71 mm

   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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: Apex2 (Bruker 2006); cell refinement: Apex2; data reduction: Apex2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2000); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C10H8ClNO2	F(000) = 432
Mr = 209.62	Dx = 1.471 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3123 reflections
a = 12.786 (2) Å	θ = 2.2–27.1°
b = 4.0070 (7) Å	µ = 0.37 mm^−1
c = 19.040 (3) Å	T = 273 K
β = 103.932 (2)°	Needle, colorless
V = 946.7 (3) Å^3	0.71 × 0.24 × 0.17 mm
Z = 4

Data collection

Bruker Apex2 CCD area-detector diffractometer	2321 independent reflections
Radiation source: fine-focus sealed tube	1674 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 28.2°, θmin = 1.7°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −17→17
Tmin = 0.778, Tmax = 0.939	k = −5→4
8678 measured reflections	l = −25→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0559P)^2 + 0.2468P] where P = (Fo^2 + 2Fc^2)/3
2321 reflections	(Δ/σ)max = 0.002
128 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.28 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
Cl	0.56243 (4)	0.46838 (15)	0.11140 (3)	0.0720 (2)
O1	0.37073 (10)	0.8089 (4)	0.50232 (7)	0.0651 (4)
O2	0.23939 (10)	0.5069 (3)	0.43190 (7)	0.0567 (3)
N1	0.48357 (10)	0.7992 (4)	0.39161 (7)	0.0457 (3)
H1A	0.5199	0.9033	0.4291	0.055*
C2	0.38397 (12)	0.6551 (4)	0.38495 (8)	0.0424 (4)
C3	0.35050 (12)	0.5122 (4)	0.31811 (9)	0.0444 (4)
H3A	0.2861	0.3989	0.3003	0.053*
C9	0.43280 (12)	0.5697 (4)	0.28113 (8)	0.0413 (3)
C4	0.44607 (13)	0.4837 (4)	0.21214 (9)	0.0477 (4)
H4A	0.3932	0.3664	0.1793	0.057*
C5	0.53987 (13)	0.5792 (5)	0.19517 (9)	0.0493 (4)
C6	0.62071 (13)	0.7604 (5)	0.24288 (10)	0.0525 (4)
H6A	0.6825	0.8229	0.2285	0.063*
C7	0.60965 (13)	0.8461 (5)	0.31024 (10)	0.0516 (4)
H7A	0.6632	0.9642	0.3424	0.062*
C8	0.51485 (11)	0.7495 (4)	0.32900 (8)	0.0418 (4)
C10	0.33332 (12)	0.6692 (4)	0.44568 (8)	0.0455 (4)
C11	0.18660 (18)	0.4908 (6)	0.49082 (12)	0.0691 (6)
H11A	0.1178	0.3840	0.4746	0.104*
H11B	0.1766	0.7126	0.5071	0.104*
H11C	0.2303	0.3651	0.5300	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0790 (4)	0.0839 (4)	0.0630 (3)	0.0040 (3)	0.0368 (3)	−0.0052 (2)
O1	0.0569 (7)	0.0895 (11)	0.0486 (7)	−0.0128 (7)	0.0118 (6)	−0.0167 (7)
O2	0.0536 (7)	0.0675 (9)	0.0517 (7)	−0.0136 (6)	0.0179 (5)	−0.0060 (6)
N1	0.0389 (6)	0.0516 (9)	0.0433 (6)	−0.0011 (6)	0.0039 (5)	−0.0047 (6)
C2	0.0382 (7)	0.0430 (9)	0.0438 (8)	0.0016 (6)	0.0057 (6)	0.0006 (7)
C3	0.0400 (7)	0.0461 (10)	0.0462 (8)	−0.0024 (6)	0.0086 (6)	−0.0023 (7)
C9	0.0383 (7)	0.0399 (8)	0.0441 (8)	0.0020 (6)	0.0066 (6)	0.0007 (6)
C4	0.0470 (8)	0.0484 (10)	0.0466 (8)	0.0001 (7)	0.0093 (7)	−0.0034 (7)
C5	0.0523 (9)	0.0497 (10)	0.0493 (9)	0.0092 (8)	0.0187 (7)	0.0040 (8)
C6	0.0411 (8)	0.0525 (11)	0.0660 (10)	0.0044 (7)	0.0171 (7)	0.0073 (9)
C7	0.0378 (7)	0.0529 (10)	0.0618 (10)	−0.0015 (7)	0.0075 (7)	0.0010 (8)
C8	0.0371 (7)	0.0408 (9)	0.0453 (8)	0.0034 (6)	0.0053 (6)	0.0010 (7)
C10	0.0429 (8)	0.0481 (10)	0.0432 (8)	0.0026 (7)	0.0059 (6)	0.0005 (7)
C11	0.0680 (12)	0.0805 (16)	0.0680 (12)	−0.0119 (11)	0.0343 (10)	−0.0029 (10)

Geometric parameters (Å, º)

Cl—C5	1.7452 (17)	C9—C8	1.411 (2)
O1—C10	1.207 (2)	C4—C5	1.370 (2)
O2—C10	1.335 (2)	C4—H4A	0.9300
O2—C11	1.443 (2)	C5—C6	1.403 (3)
N1—C8	1.360 (2)	C6—C7	1.368 (2)
N1—C2	1.376 (2)	C6—H6A	0.9300
N1—H1A	0.8600	C7—C8	1.398 (2)
C2—C3	1.367 (2)	C7—H7A	0.9300
C2—C10	1.456 (2)	C11—H11A	0.9600
C3—C9	1.419 (2)	C11—H11B	0.9600
C3—H3A	0.9300	C11—H11C	0.9600
C9—C4	1.407 (2)
C10—O2—C11	115.86 (14)	C7—C6—C5	120.71 (15)
C8—N1—C2	108.58 (13)	C7—C6—H6A	119.6
C8—N1—H1A	125.7	C5—C6—H6A	119.6
C2—N1—H1A	125.7	C6—C7—C8	117.50 (16)
C3—C2—N1	109.70 (14)	C6—C7—H7A	121.3
C3—C2—C10	131.00 (15)	C8—C7—H7A	121.3
N1—C2—C10	119.29 (14)	N1—C8—C7	129.73 (15)
C2—C3—C9	106.89 (14)	N1—C8—C9	108.12 (13)
C2—C3—H3A	126.6	C7—C8—C9	122.15 (15)
C9—C3—H3A	126.6	O1—C10—O2	123.06 (16)
C4—C9—C8	119.34 (14)	O1—C10—C2	124.83 (16)
C4—C9—C3	133.95 (15)	O2—C10—C2	112.10 (14)
C8—C9—C3	106.71 (13)	O2—C11—H11A	109.5
C5—C4—C9	117.45 (16)	O2—C11—H11B	109.5
C5—C4—H4A	121.3	H11A—C11—H11B	109.5
C9—C4—H4A	121.3	O2—C11—H11C	109.5
C4—C5—C6	122.84 (16)	H11A—C11—H11C	109.5
C4—C5—Cl	119.42 (14)	H11B—C11—H11C	109.5
C6—C5—Cl	117.73 (13)
C8—N1—C2—C3	−0.05 (19)	C2—N1—C8—C9	0.17 (18)
C8—N1—C2—C10	178.95 (14)	C6—C7—C8—N1	179.56 (16)
N1—C2—C3—C9	−0.08 (19)	C6—C7—C8—C9	0.1 (3)
C10—C2—C3—C9	−178.93 (17)	C4—C9—C8—N1	−179.55 (14)
C2—C3—C9—C4	179.37 (18)	C3—C9—C8—N1	−0.21 (18)
C2—C3—C9—C8	0.18 (18)	C4—C9—C8—C7	0.0 (2)
C8—C9—C4—C5	0.4 (2)	C3—C9—C8—C7	179.32 (16)
C3—C9—C4—C5	−178.70 (17)	C11—O2—C10—O1	−3.4 (3)
C9—C4—C5—C6	−1.0 (3)	C11—O2—C10—C2	176.40 (15)
C9—C4—C5—Cl	178.08 (12)	C3—C2—C10—O1	−178.88 (19)
C4—C5—C6—C7	1.1 (3)	N1—C2—C10—O1	2.4 (3)
Cl—C5—C6—C7	−177.93 (14)	C3—C2—C10—O2	1.3 (3)
C5—C6—C7—C8	−0.7 (3)	N1—C2—C10—O2	−177.42 (15)
C2—N1—C8—C7	−179.32 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	2.03	2.8641 (19)	164

Symmetry code: (i) −x+1, −y+2, −z+1.