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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032181/hk2103sup1.cif
Contains datablocks global, I, publication_text

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032181/hk2103Isup2.hkl
Contains datablock I

CCDC reference: 621365

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

Computing details top

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) top
Crystal data top
C10H8ClNO2F(000) = 432
Mr = 209.62Dx = 1.471 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3123 reflections
a = 12.786 (2) Åθ = 2.2–27.1°
b = 4.0070 (7) ŵ = 0.37 mm1
c = 19.040 (3) ÅT = 273 K
β = 103.932 (2)°Needle, colorless
V = 946.7 (3) Å30.71 × 0.24 × 0.17 mm
Z = 4
Data collection top
Bruker Apex2 CCD area-detector
diffractometer
2321 independent reflections
Radiation source: fine-focus sealed tube1674 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 28.2°, θmin = 1.7°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
h = 1717
Tmin = 0.778, Tmax = 0.939k = 54
8678 measured reflectionsl = 2525
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.2468P]
where P = (Fo2 + 2Fc2)/3
2321 reflections(Δ/σ)max = 0.002
128 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl0.56243 (4)0.46838 (15)0.11140 (3)0.0720 (2)
O10.37073 (10)0.8089 (4)0.50232 (7)0.0651 (4)
O20.23939 (10)0.5069 (3)0.43190 (7)0.0567 (3)
N10.48357 (10)0.7992 (4)0.39161 (7)0.0457 (3)
H1A0.51990.90330.42910.055*
C20.38397 (12)0.6551 (4)0.38495 (8)0.0424 (4)
C30.35050 (12)0.5122 (4)0.31811 (9)0.0444 (4)
H3A0.28610.39890.30030.053*
C90.43280 (12)0.5697 (4)0.28113 (8)0.0413 (3)
C40.44607 (13)0.4837 (4)0.21214 (9)0.0477 (4)
H4A0.39320.36640.17930.057*
C50.53987 (13)0.5792 (5)0.19517 (9)0.0493 (4)
C60.62071 (13)0.7604 (5)0.24288 (10)0.0525 (4)
H6A0.68250.82290.22850.063*
C70.60965 (13)0.8461 (5)0.31024 (10)0.0516 (4)
H7A0.66320.96420.34240.062*
C80.51485 (11)0.7495 (4)0.32900 (8)0.0418 (4)
C100.33332 (12)0.6692 (4)0.44568 (8)0.0455 (4)
C110.18660 (18)0.4908 (6)0.49082 (12)0.0691 (6)
H11A0.11780.38400.47460.104*
H11B0.17660.71260.50710.104*
H11C0.23030.36510.53000.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0790 (4)0.0839 (4)0.0630 (3)0.0040 (3)0.0368 (3)0.0052 (2)
O10.0569 (7)0.0895 (11)0.0486 (7)0.0128 (7)0.0118 (6)0.0167 (7)
O20.0536 (7)0.0675 (9)0.0517 (7)0.0136 (6)0.0179 (5)0.0060 (6)
N10.0389 (6)0.0516 (9)0.0433 (6)0.0011 (6)0.0039 (5)0.0047 (6)
C20.0382 (7)0.0430 (9)0.0438 (8)0.0016 (6)0.0057 (6)0.0006 (7)
C30.0400 (7)0.0461 (10)0.0462 (8)0.0024 (6)0.0086 (6)0.0023 (7)
C90.0383 (7)0.0399 (8)0.0441 (8)0.0020 (6)0.0066 (6)0.0007 (6)
C40.0470 (8)0.0484 (10)0.0466 (8)0.0001 (7)0.0093 (7)0.0034 (7)
C50.0523 (9)0.0497 (10)0.0493 (9)0.0092 (8)0.0187 (7)0.0040 (8)
C60.0411 (8)0.0525 (11)0.0660 (10)0.0044 (7)0.0171 (7)0.0073 (9)
C70.0378 (7)0.0529 (10)0.0618 (10)0.0015 (7)0.0075 (7)0.0010 (8)
C80.0371 (7)0.0408 (9)0.0453 (8)0.0034 (6)0.0053 (6)0.0010 (7)
C100.0429 (8)0.0481 (10)0.0432 (8)0.0026 (7)0.0059 (6)0.0005 (7)
C110.0680 (12)0.0805 (16)0.0680 (12)0.0119 (11)0.0343 (10)0.0029 (10)
Geometric parameters (Å, º) top
Cl—C51.7452 (17)C9—C81.411 (2)
O1—C101.207 (2)C4—C51.370 (2)
O2—C101.335 (2)C4—H4A0.9300
O2—C111.443 (2)C5—C61.403 (3)
N1—C81.360 (2)C6—C71.368 (2)
N1—C21.376 (2)C6—H6A0.9300
N1—H1A0.8600C7—C81.398 (2)
C2—C31.367 (2)C7—H7A0.9300
C2—C101.456 (2)C11—H11A0.9600
C3—C91.419 (2)C11—H11B0.9600
C3—H3A0.9300C11—H11C0.9600
C9—C41.407 (2)
C10—O2—C11115.86 (14)C7—C6—C5120.71 (15)
C8—N1—C2108.58 (13)C7—C6—H6A119.6
C8—N1—H1A125.7C5—C6—H6A119.6
C2—N1—H1A125.7C6—C7—C8117.50 (16)
C3—C2—N1109.70 (14)C6—C7—H7A121.3
C3—C2—C10131.00 (15)C8—C7—H7A121.3
N1—C2—C10119.29 (14)N1—C8—C7129.73 (15)
C2—C3—C9106.89 (14)N1—C8—C9108.12 (13)
C2—C3—H3A126.6C7—C8—C9122.15 (15)
C9—C3—H3A126.6O1—C10—O2123.06 (16)
C4—C9—C8119.34 (14)O1—C10—C2124.83 (16)
C4—C9—C3133.95 (15)O2—C10—C2112.10 (14)
C8—C9—C3106.71 (13)O2—C11—H11A109.5
C5—C4—C9117.45 (16)O2—C11—H11B109.5
C5—C4—H4A121.3H11A—C11—H11B109.5
C9—C4—H4A121.3O2—C11—H11C109.5
C4—C5—C6122.84 (16)H11A—C11—H11C109.5
C4—C5—Cl119.42 (14)H11B—C11—H11C109.5
C6—C5—Cl117.73 (13)
C8—N1—C2—C30.05 (19)C2—N1—C8—C90.17 (18)
C8—N1—C2—C10178.95 (14)C6—C7—C8—N1179.56 (16)
N1—C2—C3—C90.08 (19)C6—C7—C8—C90.1 (3)
C10—C2—C3—C9178.93 (17)C4—C9—C8—N1179.55 (14)
C2—C3—C9—C4179.37 (18)C3—C9—C8—N10.21 (18)
C2—C3—C9—C80.18 (18)C4—C9—C8—C70.0 (2)
C8—C9—C4—C50.4 (2)C3—C9—C8—C7179.32 (16)
C3—C9—C4—C5178.70 (17)C11—O2—C10—O13.4 (3)
C9—C4—C5—C61.0 (3)C11—O2—C10—C2176.40 (15)
C9—C4—C5—Cl178.08 (12)C3—C2—C10—O1178.88 (19)
C4—C5—C6—C71.1 (3)N1—C2—C10—O12.4 (3)
Cl—C5—C6—C7177.93 (14)C3—C2—C10—O21.3 (3)
C5—C6—C7—C80.7 (3)N1—C2—C10—O2177.42 (15)
C2—N1—C8—C7179.32 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.032.8641 (19)164
Symmetry code: (i) x+1, y+2, z+1.
 

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