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In the title compound, C15H17BrN2O, the amide group is twisted out of π-conjugation with the indole double bond due to steric hindrance by the Br atom. The piperidine ring adopts a chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017928/ci2341sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017928/ci2341Isup2.hkl
Contains datablock I

CCDC reference: 647161

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.019 Å
  • R factor = 0.061
  • wR factor = 0.245
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.83
Author Response: ...Data collected on an old Rigaku AFC6S diffractometer
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91
Author Response: ...Data collected on an old Rigaku AFC6S diffractometer

Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 32 Perc. PLAT213_ALERT_2_B Atom C2 has ADP max/min Ratio ............. 4.70 oblat PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 19 PLAT413_ALERT_2_B Short Inter XH3 .. XHn H6 .. H17 .. 2.07 Ang.
Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.85 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for Br1 - C2 .. 6.64 su PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C4 -C9 1.34 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.849 Tmax scaled 0.372 Tmin scaled 0.246 REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 2370 From the CIF: _diffrn_reflns_limit_ max hkl 9. 8. 14. From the CIF: _diffrn_reflns_limit_ min hkl -10. 0. -13. TEST1: Expected hkl limits for theta max Calculated maximum hkl 10. 10. 14. Calculated minimum hkl -10. -10. -14.
2 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994)'; cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

1-(2-Bromo-1-methylindol-3-ylcarbonyl)piperidine top
Crystal data top
C15H17BrN2OZ = 2
Mr = 321.22F(000) = 328
Triclinic, P1Dx = 1.717 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 7.819 (3) ÅCell parameters from 8 reflections
b = 8.218 (3) Åθ = 6.2–12.0°
c = 11.114 (5) ŵ = 3.30 mm1
α = 69.99 (3)°T = 296 K
β = 91.21 (4)°Prism, colorless
γ = 111.16 (3)°0.50 × 0.30 × 0.30 mm
V = 621.5 (4) Å3
Data collection top
Rigaku AFC-6S
diffractometer
750 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
ω/2θ scansh = 109
Absorption correction: ψ scan
(North et al., 1968)
k = 08
Tmin = 0.289, Tmax = 0.438l = 1314
2370 measured reflections3 standard reflections every 150 reflections
2370 independent reflections intensity decay: 4.3%
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245All H-atom parameters refined
S = 0.95 w = 1/[σ2(Fo2) + (0.1228P)2]
where P = (Fo2 + 2Fc2)/3
2370 reflections(Δ/σ)max = 0.001
173 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.91 e Å3
Special details top

Experimental. 1H-NMR (CDCl3) δ 7.46–7.49 (m, 1H), 7.07–7.26 (m, 3H), 3.73 (bs, 5H), 1.59 (m, 8H); 13C-NMR (500 MHz, CDCl3, -50°C) δ 164.5, 135.6, 125.0, 122.1, 120.6, 118.6, 113.9, 110.7, 109.5, 48.2, 42.7, 31.4, 26.6, 25.4, 24.1.

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
Br11.0355 (2)0.2788 (2)1.05707 (13)0.0744 (7)
O11.1437 (13)0.4727 (11)0.7357 (8)0.070 (2)
N10.7622 (13)0.0009 (14)1.0107 (10)0.054 (2)
N20.9076 (13)0.5477 (14)0.6866 (9)0.058 (3)
C20.8793 (16)0.1756 (17)0.9583 (11)0.051 (3)
C30.8640 (15)0.2512 (18)0.8363 (11)0.051 (3)
C40.7300 (16)0.1130 (17)0.8096 (13)0.052 (3)
C50.6518 (18)0.1029 (19)0.7008 (12)0.060 (3)
H10.68850.20610.62440.073*
C60.5241 (19)0.055 (2)0.7059 (14)0.066 (3)
H20.47340.06290.63060.079*
C70.4624 (18)0.205 (2)0.814 (2)0.079 (4)
H30.36930.31450.81330.095*
C80.5366 (18)0.198 (2)0.9239 (13)0.065 (3)
H40.49740.30141.00030.078*
C90.6669 (17)0.0386 (18)0.9189 (15)0.059 (3)
C100.7359 (18)0.1226 (16)1.1413 (11)0.072 (4)
H50.81690.18951.15190.086*
H60.61010.20971.16290.086*
H70.76290.05161.19710.086*
C110.984 (2)0.4319 (16)0.7529 (11)0.055 (3)
C121.0136 (16)0.7211 (15)0.5986 (11)0.062 (3)
H81.13340.72260.57610.074*
H91.03240.81580.63630.074*
C130.9209 (18)0.7624 (18)0.4831 (11)0.068 (3)
H100.91180.67410.44120.081*
H110.99210.88710.42310.081*
C140.7349 (18)0.7499 (17)0.5181 (12)0.068 (4)
H120.74470.84670.55210.082*
H130.67100.77010.44180.082*
C150.6307 (17)0.5697 (18)0.6131 (12)0.072 (4)
H140.60910.47450.57540.086*
H150.51170.56710.63880.086*
C160.7277 (16)0.5265 (16)0.7278 (11)0.059 (3)
H160.73550.61080.77290.071*
H170.66100.39940.78610.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0853 (11)0.0846 (11)0.0695 (10)0.0413 (8)0.0240 (7)0.0377 (8)
O10.057 (6)0.054 (5)0.088 (6)0.013 (5)0.003 (5)0.019 (5)
N10.048 (6)0.048 (7)0.069 (7)0.019 (6)0.011 (6)0.026 (6)
N20.046 (7)0.056 (7)0.055 (6)0.017 (6)0.006 (5)0.003 (6)
C20.053 (7)0.053 (8)0.062 (9)0.010 (7)0.029 (7)0.051 (8)
C30.044 (7)0.071 (10)0.054 (8)0.025 (7)0.019 (6)0.038 (8)
C40.050 (8)0.047 (8)0.064 (9)0.022 (7)0.001 (7)0.022 (8)
C50.064 (9)0.060 (9)0.062 (9)0.019 (8)0.008 (7)0.033 (7)
C60.066 (9)0.070 (10)0.073 (10)0.028 (8)0.022 (8)0.037 (9)
C70.055 (9)0.057 (10)0.133 (14)0.015 (8)0.005 (10)0.049 (11)
C80.059 (9)0.068 (10)0.076 (10)0.027 (8)0.009 (8)0.030 (8)
C90.050 (8)0.038 (8)0.094 (11)0.009 (7)0.001 (8)0.039 (9)
C100.096 (10)0.060 (8)0.052 (8)0.037 (8)0.006 (7)0.003 (7)
C110.056 (9)0.045 (9)0.051 (8)0.001 (8)0.001 (8)0.022 (7)
C120.061 (8)0.039 (8)0.063 (8)0.008 (7)0.009 (7)0.003 (7)
C130.080 (10)0.066 (8)0.047 (8)0.025 (7)0.006 (7)0.009 (7)
C140.075 (10)0.064 (9)0.056 (8)0.023 (8)0.018 (7)0.015 (7)
C150.061 (8)0.072 (10)0.070 (9)0.020 (7)0.000 (8)0.016 (8)
C160.056 (9)0.052 (8)0.057 (8)0.014 (6)0.011 (7)0.013 (6)
Geometric parameters (Å, º) top
Br1—C21.803 (9)C8—C91.321 (17)
O1—C111.170 (13)C8—H40.93
N1—C91.312 (15)C10—H50.96
N1—C21.319 (14)C10—H60.96
N1—C101.426 (14)C10—H70.96
N2—C111.312 (14)C12—C131.459 (15)
N2—C121.379 (14)C12—H80.97
N2—C161.419 (14)C12—H90.97
C2—C31.307 (15)C13—C141.472 (16)
C3—C41.354 (16)C13—H100.97
C3—C111.427 (16)C13—H110.97
C4—C91.349 (16)C14—C151.438 (16)
C4—C51.358 (15)C14—H120.97
C5—C61.303 (16)C14—H130.97
C5—H10.93C15—C161.473 (16)
C6—C71.334 (18)C15—H140.97
C6—H20.93C15—H150.97
C7—C81.355 (18)C16—H160.97
C7—H30.93C16—H170.97
C9—N1—C2106.3 (10)H6—C10—H7109.5
C9—N1—C10125.4 (11)O1—C11—N2120.3 (11)
C2—N1—C10128.3 (11)O1—C11—C3122.2 (13)
C11—N2—C12120.8 (10)N2—C11—C3117.3 (12)
C11—N2—C16121.1 (10)N2—C12—C13109.7 (10)
C12—N2—C16115.5 (10)N2—C12—H8109.7
C3—C2—N1112.7 (10)C13—C12—H8109.7
C3—C2—Br1128.5 (11)N2—C12—H9109.7
N1—C2—Br1118.8 (9)C13—C12—H9109.7
C2—C3—C4104.4 (12)H8—C12—H9108.2
C2—C3—C11124.6 (11)C12—C13—C14109.8 (10)
C4—C3—C11130.5 (11)C12—C13—H10109.7
C9—C4—C3108.4 (12)C14—C13—H10109.7
C9—C4—C5118.3 (12)C12—C13—H11109.7
C3—C4—C5133.2 (13)C14—C13—H11109.7
C6—C5—C4118.5 (12)H10—C13—H11108.2
C6—C5—H1120.8C15—C14—C13110.6 (11)
C4—C5—H1120.8C15—C14—H12109.5
C5—C6—C7123.2 (14)C13—C14—H12109.5
C5—C6—H2118.4C15—C14—H13109.5
C7—C6—H2118.4C13—C14—H13109.5
C6—C7—C8119.4 (12)H12—C14—H13108.1
C6—C7—H3120.3C14—C15—C16111.8 (11)
C8—C7—H3120.3C14—C15—H14109.3
C9—C8—C7117.5 (14)C16—C15—H14109.3
C9—C8—H4121.2C14—C15—H15109.3
C7—C8—H4121.2C16—C15—H15109.3
N1—C9—C8128.8 (15)H14—C15—H15107.9
N1—C9—C4108.2 (11)N2—C16—C15108.3 (10)
C8—C9—C4123.0 (14)N2—C16—H16110.0
N1—C10—H5109.5C15—C16—H16110.0
N1—C10—H6109.5N2—C16—H17110.0
H5—C10—H6109.5C15—C16—H17110.0
N1—C10—H7109.5H16—C16—H17108.4
H5—C10—H7109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H3···O1i0.932.383.27 (2)160
C10—H5···O1ii0.962.363.200 (17)145
C16—H16···Br1iii0.972.733.464 (13)133
Symmetry codes: (i) x1, y1, z; (ii) x+2, y, z+2; (iii) x+2, y+1, z+2.
 

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