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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
CCDC reference: 647161
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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
C15H17BrN2O | Z = 2 |
Mr = 321.22 | F(000) = 328 |
Triclinic, P1 | Dx = 1.717 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 7.819 (3) Å | Cell parameters from 8 reflections |
b = 8.218 (3) Å | θ = 6.2–12.0° |
c = 11.114 (5) Å | µ = 3.30 mm−1 |
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 tube | Rint = 0.000 |
Graphite monochromator | θmax = 27.5°, θmin = 2.0° |
ω/2θ scans | h = −10→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→8 |
Tmin = 0.289, Tmax = 0.438 | l = −13→14 |
2370 measured reflections | 3 standard reflections every 150 reflections |
2370 independent reflections | intensity decay: −4.3% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.245 | All 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 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.91 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 1.0355 (2) | 0.2788 (2) | 1.05707 (13) | 0.0744 (7) | |
O1 | 1.1437 (13) | 0.4727 (11) | 0.7357 (8) | 0.070 (2) | |
N1 | 0.7622 (13) | 0.0009 (14) | 1.0107 (10) | 0.054 (2) | |
N2 | 0.9076 (13) | 0.5477 (14) | 0.6866 (9) | 0.058 (3) | |
C2 | 0.8793 (16) | 0.1756 (17) | 0.9583 (11) | 0.051 (3) | |
C3 | 0.8640 (15) | 0.2512 (18) | 0.8363 (11) | 0.051 (3) | |
C4 | 0.7300 (16) | 0.1130 (17) | 0.8096 (13) | 0.052 (3) | |
C5 | 0.6518 (18) | 0.1029 (19) | 0.7008 (12) | 0.060 (3) | |
H1 | 0.6885 | 0.2061 | 0.6244 | 0.073* | |
C6 | 0.5241 (19) | −0.055 (2) | 0.7059 (14) | 0.066 (3) | |
H2 | 0.4734 | −0.0629 | 0.6306 | 0.079* | |
C7 | 0.4624 (18) | −0.205 (2) | 0.814 (2) | 0.079 (4) | |
H3 | 0.3693 | −0.3145 | 0.8133 | 0.095* | |
C8 | 0.5366 (18) | −0.198 (2) | 0.9239 (13) | 0.065 (3) | |
H4 | 0.4974 | −0.3014 | 1.0003 | 0.078* | |
C9 | 0.6669 (17) | −0.0386 (18) | 0.9189 (15) | 0.059 (3) | |
C10 | 0.7359 (18) | −0.1226 (16) | 1.1413 (11) | 0.072 (4) | |
H5 | 0.8169 | −0.1895 | 1.1519 | 0.086* | |
H6 | 0.6101 | −0.2097 | 1.1629 | 0.086* | |
H7 | 0.7629 | −0.0516 | 1.1971 | 0.086* | |
C11 | 0.984 (2) | 0.4319 (16) | 0.7529 (11) | 0.055 (3) | |
C12 | 1.0136 (16) | 0.7211 (15) | 0.5986 (11) | 0.062 (3) | |
H8 | 1.1334 | 0.7226 | 0.5761 | 0.074* | |
H9 | 1.0324 | 0.8158 | 0.6363 | 0.074* | |
C13 | 0.9209 (18) | 0.7624 (18) | 0.4831 (11) | 0.068 (3) | |
H10 | 0.9118 | 0.6741 | 0.4412 | 0.081* | |
H11 | 0.9921 | 0.8871 | 0.4231 | 0.081* | |
C14 | 0.7349 (18) | 0.7499 (17) | 0.5181 (12) | 0.068 (4) | |
H12 | 0.7447 | 0.8467 | 0.5521 | 0.082* | |
H13 | 0.6710 | 0.7701 | 0.4418 | 0.082* | |
C15 | 0.6307 (17) | 0.5697 (18) | 0.6131 (12) | 0.072 (4) | |
H14 | 0.6091 | 0.4745 | 0.5754 | 0.086* | |
H15 | 0.5117 | 0.5671 | 0.6388 | 0.086* | |
C16 | 0.7277 (16) | 0.5265 (16) | 0.7278 (11) | 0.059 (3) | |
H16 | 0.7355 | 0.6108 | 0.7729 | 0.071* | |
H17 | 0.6610 | 0.3994 | 0.7861 | 0.071* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0853 (11) | 0.0846 (11) | 0.0695 (10) | 0.0413 (8) | −0.0240 (7) | −0.0377 (8) |
O1 | 0.057 (6) | 0.054 (5) | 0.088 (6) | 0.013 (5) | −0.003 (5) | −0.019 (5) |
N1 | 0.048 (6) | 0.048 (7) | 0.069 (7) | 0.019 (6) | −0.011 (6) | −0.026 (6) |
N2 | 0.046 (7) | 0.056 (7) | 0.055 (6) | 0.017 (6) | 0.006 (5) | −0.003 (6) |
C2 | 0.053 (7) | 0.053 (8) | 0.062 (9) | 0.010 (7) | −0.029 (7) | −0.051 (8) |
C3 | 0.044 (7) | 0.071 (10) | 0.054 (8) | 0.025 (7) | −0.019 (6) | −0.038 (8) |
C4 | 0.050 (8) | 0.047 (8) | 0.064 (9) | 0.022 (7) | −0.001 (7) | −0.022 (8) |
C5 | 0.064 (9) | 0.060 (9) | 0.062 (9) | 0.019 (8) | −0.008 (7) | −0.033 (7) |
C6 | 0.066 (9) | 0.070 (10) | 0.073 (10) | 0.028 (8) | −0.022 (8) | −0.037 (9) |
C7 | 0.055 (9) | 0.057 (10) | 0.133 (14) | 0.015 (8) | −0.005 (10) | −0.049 (11) |
C8 | 0.059 (9) | 0.068 (10) | 0.076 (10) | 0.027 (8) | 0.009 (8) | −0.030 (8) |
C9 | 0.050 (8) | 0.038 (8) | 0.094 (11) | 0.009 (7) | −0.001 (8) | −0.039 (9) |
C10 | 0.096 (10) | 0.060 (8) | 0.052 (8) | 0.037 (8) | 0.006 (7) | −0.003 (7) |
C11 | 0.056 (9) | 0.045 (9) | 0.051 (8) | 0.001 (8) | 0.001 (8) | −0.022 (7) |
C12 | 0.061 (8) | 0.039 (8) | 0.063 (8) | 0.008 (7) | 0.009 (7) | −0.003 (7) |
C13 | 0.080 (10) | 0.066 (8) | 0.047 (8) | 0.025 (7) | −0.006 (7) | −0.009 (7) |
C14 | 0.075 (10) | 0.064 (9) | 0.056 (8) | 0.023 (8) | −0.018 (7) | −0.015 (7) |
C15 | 0.061 (8) | 0.072 (10) | 0.070 (9) | 0.020 (7) | 0.000 (8) | −0.016 (8) |
C16 | 0.056 (9) | 0.052 (8) | 0.057 (8) | 0.014 (6) | −0.011 (7) | −0.013 (6) |
Geometric parameters (Å, º) top
Br1—C2 | 1.803 (9) | C8—C9 | 1.321 (17) |
O1—C11 | 1.170 (13) | C8—H4 | 0.93 |
N1—C9 | 1.312 (15) | C10—H5 | 0.96 |
N1—C2 | 1.319 (14) | C10—H6 | 0.96 |
N1—C10 | 1.426 (14) | C10—H7 | 0.96 |
N2—C11 | 1.312 (14) | C12—C13 | 1.459 (15) |
N2—C12 | 1.379 (14) | C12—H8 | 0.97 |
N2—C16 | 1.419 (14) | C12—H9 | 0.97 |
C2—C3 | 1.307 (15) | C13—C14 | 1.472 (16) |
C3—C4 | 1.354 (16) | C13—H10 | 0.97 |
C3—C11 | 1.427 (16) | C13—H11 | 0.97 |
C4—C9 | 1.349 (16) | C14—C15 | 1.438 (16) |
C4—C5 | 1.358 (15) | C14—H12 | 0.97 |
C5—C6 | 1.303 (16) | C14—H13 | 0.97 |
C5—H1 | 0.93 | C15—C16 | 1.473 (16) |
C6—C7 | 1.334 (18) | C15—H14 | 0.97 |
C6—H2 | 0.93 | C15—H15 | 0.97 |
C7—C8 | 1.355 (18) | C16—H16 | 0.97 |
C7—H3 | 0.93 | C16—H17 | 0.97 |
| | | |
C9—N1—C2 | 106.3 (10) | H6—C10—H7 | 109.5 |
C9—N1—C10 | 125.4 (11) | O1—C11—N2 | 120.3 (11) |
C2—N1—C10 | 128.3 (11) | O1—C11—C3 | 122.2 (13) |
C11—N2—C12 | 120.8 (10) | N2—C11—C3 | 117.3 (12) |
C11—N2—C16 | 121.1 (10) | N2—C12—C13 | 109.7 (10) |
C12—N2—C16 | 115.5 (10) | N2—C12—H8 | 109.7 |
C3—C2—N1 | 112.7 (10) | C13—C12—H8 | 109.7 |
C3—C2—Br1 | 128.5 (11) | N2—C12—H9 | 109.7 |
N1—C2—Br1 | 118.8 (9) | C13—C12—H9 | 109.7 |
C2—C3—C4 | 104.4 (12) | H8—C12—H9 | 108.2 |
C2—C3—C11 | 124.6 (11) | C12—C13—C14 | 109.8 (10) |
C4—C3—C11 | 130.5 (11) | C12—C13—H10 | 109.7 |
C9—C4—C3 | 108.4 (12) | C14—C13—H10 | 109.7 |
C9—C4—C5 | 118.3 (12) | C12—C13—H11 | 109.7 |
C3—C4—C5 | 133.2 (13) | C14—C13—H11 | 109.7 |
C6—C5—C4 | 118.5 (12) | H10—C13—H11 | 108.2 |
C6—C5—H1 | 120.8 | C15—C14—C13 | 110.6 (11) |
C4—C5—H1 | 120.8 | C15—C14—H12 | 109.5 |
C5—C6—C7 | 123.2 (14) | C13—C14—H12 | 109.5 |
C5—C6—H2 | 118.4 | C15—C14—H13 | 109.5 |
C7—C6—H2 | 118.4 | C13—C14—H13 | 109.5 |
C6—C7—C8 | 119.4 (12) | H12—C14—H13 | 108.1 |
C6—C7—H3 | 120.3 | C14—C15—C16 | 111.8 (11) |
C8—C7—H3 | 120.3 | C14—C15—H14 | 109.3 |
C9—C8—C7 | 117.5 (14) | C16—C15—H14 | 109.3 |
C9—C8—H4 | 121.2 | C14—C15—H15 | 109.3 |
C7—C8—H4 | 121.2 | C16—C15—H15 | 109.3 |
N1—C9—C8 | 128.8 (15) | H14—C15—H15 | 107.9 |
N1—C9—C4 | 108.2 (11) | N2—C16—C15 | 108.3 (10) |
C8—C9—C4 | 123.0 (14) | N2—C16—H16 | 110.0 |
N1—C10—H5 | 109.5 | C15—C16—H16 | 110.0 |
N1—C10—H6 | 109.5 | N2—C16—H17 | 110.0 |
H5—C10—H6 | 109.5 | C15—C16—H17 | 110.0 |
N1—C10—H7 | 109.5 | H16—C16—H17 | 108.4 |
H5—C10—H7 | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H3···O1i | 0.93 | 2.38 | 3.27 (2) | 160 |
C10—H5···O1ii | 0.96 | 2.36 | 3.200 (17) | 145 |
C16—H16···Br1iii | 0.97 | 2.73 | 3.464 (13) | 133 |
Symmetry codes: (i) x−1, y−1, z; (ii) −x+2, −y, −z+2; (iii) −x+2, −y+1, −z+2. |
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