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The mol­ecular structure of the title compound, C20H22N2O, shows elongated C—C single bonds due to their thermal lability. The crystal packing shows mol­ecules linked via inter­molecular C—H...O hydrogen bonds, forming infinite chains along [010].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603203X/om2049sup1.cif
Contains datablocks IV, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603203X/om2049IVsup2.hkl
Contains datablock IV

CCDC reference: 621460

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.080
  • Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C8 - C18 .. 7.07 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 2103 Count of symmetry unique reflns 2102 Completeness (_total/calc) 100.05% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

rel-(1R,4R,9R)-1-Acetyl-9-(1-piperidinyl)-1,4-dihydro-1,4-ethanonaphthalene- 9-carbonitrile top
Crystal data top
C20H22N2OF(000) = 656
Mr = 306.40Dx = 1.215 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 8.869 (2) Åθ = 10–20°
b = 10.552 (2) ŵ = 0.08 mm1
c = 17.902 (4) ÅT = 150 K
V = 1675.4 (6) Å3Prism, colourless
Z = 40.59 × 0.22 × 0.22 mm
Data collection top
Siemens P4 rotating-anode
diffractometer
1923 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.0°, θmin = 2.2°
ω scansh = 1111
Absorption correction: ψ scan
(North et al., 1968)
k = 013
Tmin = 0.961, Tmax = 0.981l = 022
3963 measured reflections3 standard reflections every 100 reflections
2103 independent reflections intensity decay: <0.01%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.038P)2 + 0.3818P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2103 reflectionsΔρmax = 0.22 e Å3
209 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.045 (2)
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
N10.10591 (14)0.91818 (11)0.13996 (6)0.0192 (3)
N20.10922 (19)1.09473 (14)0.02094 (8)0.0368 (3)
O10.37247 (13)0.75150 (10)0.25539 (7)0.0301 (3)
C10.11245 (16)0.95357 (13)0.30753 (7)0.0181 (3)
C20.10488 (17)0.88912 (14)0.37524 (8)0.0213 (3)
H2A0.18590.83670.39100.026*
C30.02340 (18)0.90257 (15)0.41970 (8)0.0253 (3)
H3A0.02910.85980.46630.030*
C40.14245 (17)0.97781 (14)0.39637 (8)0.0235 (3)
H4A0.22990.98520.42670.028*
C50.13461 (17)1.04302 (14)0.32836 (8)0.0203 (3)
H5A0.21621.09460.31240.024*
C60.00612 (16)1.03138 (12)0.28460 (8)0.0180 (3)
C70.02183 (16)1.09686 (13)0.21052 (8)0.0192 (3)
H7A0.05981.15870.19800.023*
C80.03605 (17)0.98876 (13)0.15005 (8)0.0186 (3)
C90.16353 (16)0.89676 (14)0.17676 (8)0.0202 (3)
H9A0.24020.88800.13690.024*
H9B0.12010.81190.18660.024*
C100.23995 (16)0.94803 (13)0.24935 (8)0.0194 (3)
C110.28802 (17)1.08413 (14)0.23340 (8)0.0229 (3)
H11A0.38941.11240.23750.028*
C120.17572 (17)1.15923 (14)0.21334 (8)0.0230 (3)
H12A0.19041.24610.20150.028*
C130.23922 (18)0.99818 (15)0.12690 (9)0.0254 (3)
H13A0.24551.06430.16600.030*
H13B0.23041.04070.07780.030*
C140.38070 (19)0.91719 (18)0.12849 (10)0.0337 (4)
H14A0.39160.87880.17870.040*
H14B0.46960.97180.11960.040*
C150.3773 (2)0.81240 (16)0.07012 (9)0.0315 (4)
H15A0.46490.75540.07720.038*
H15B0.38390.84980.01950.038*
C160.2313 (2)0.73703 (15)0.07764 (9)0.0297 (4)
H16A0.22230.67740.03520.036*
H16B0.23420.68680.12430.036*
C170.09455 (18)0.82418 (14)0.07890 (8)0.0243 (3)
H17A0.08660.86900.03050.029*
H17B0.00210.77290.08570.029*
C180.08170 (18)1.05052 (15)0.07787 (9)0.0242 (3)
C190.36556 (17)0.86078 (14)0.27651 (8)0.0229 (3)
C200.47743 (18)0.91374 (18)0.33149 (9)0.0324 (4)
H20A0.55180.96560.30490.049*
H20B0.42450.96620.36830.049*
H20C0.52880.84390.35710.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0228 (6)0.0180 (6)0.0167 (5)0.0003 (5)0.0028 (5)0.0036 (5)
N20.0529 (9)0.0348 (8)0.0228 (7)0.0027 (8)0.0055 (7)0.0024 (6)
O10.0253 (6)0.0253 (6)0.0397 (6)0.0039 (5)0.0055 (5)0.0005 (5)
C10.0200 (7)0.0160 (6)0.0182 (6)0.0054 (6)0.0008 (5)0.0035 (5)
C20.0242 (7)0.0197 (7)0.0200 (7)0.0022 (6)0.0036 (6)0.0003 (5)
C30.0343 (8)0.0245 (7)0.0171 (7)0.0070 (7)0.0003 (6)0.0007 (6)
C40.0241 (7)0.0249 (7)0.0215 (7)0.0072 (6)0.0040 (6)0.0060 (6)
C50.0221 (7)0.0172 (6)0.0214 (7)0.0028 (6)0.0023 (6)0.0061 (6)
C60.0231 (7)0.0137 (6)0.0173 (6)0.0034 (6)0.0022 (6)0.0036 (5)
C70.0260 (7)0.0155 (6)0.0161 (6)0.0006 (6)0.0013 (6)0.0021 (6)
C80.0237 (7)0.0169 (7)0.0151 (6)0.0002 (5)0.0001 (5)0.0010 (5)
C90.0228 (7)0.0190 (7)0.0190 (7)0.0004 (6)0.0010 (5)0.0022 (6)
C100.0194 (6)0.0204 (7)0.0184 (7)0.0023 (6)0.0001 (6)0.0005 (6)
C110.0247 (7)0.0240 (7)0.0201 (7)0.0097 (6)0.0013 (6)0.0015 (6)
C120.0323 (8)0.0182 (7)0.0185 (7)0.0073 (6)0.0024 (6)0.0007 (6)
C130.0261 (8)0.0244 (7)0.0257 (7)0.0026 (6)0.0040 (6)0.0057 (6)
C140.0245 (8)0.0410 (9)0.0355 (9)0.0021 (8)0.0002 (7)0.0075 (8)
C150.0343 (9)0.0340 (9)0.0260 (8)0.0110 (8)0.0077 (7)0.0018 (7)
C160.0446 (10)0.0225 (7)0.0220 (7)0.0045 (7)0.0107 (7)0.0014 (6)
C170.0313 (8)0.0216 (7)0.0199 (7)0.0029 (6)0.0047 (6)0.0054 (6)
C180.0293 (8)0.0206 (7)0.0228 (7)0.0000 (6)0.0015 (6)0.0023 (6)
C190.0184 (7)0.0287 (8)0.0217 (7)0.0013 (6)0.0010 (6)0.0020 (6)
C200.0236 (8)0.0438 (10)0.0297 (8)0.0011 (7)0.0072 (7)0.0049 (8)
Geometric parameters (Å, º) top
N1—C131.471 (2)C9—H9B0.9900
N1—C81.4739 (18)C10—C191.525 (2)
N1—C171.4795 (18)C10—C111.525 (2)
N2—C181.147 (2)C11—C121.322 (2)
O1—C191.2151 (18)C11—H11A0.9500
C1—C21.392 (2)C12—H12A0.9500
C1—C61.396 (2)C13—C141.518 (2)
C1—C101.5385 (19)C13—H13A0.9900
C2—C31.396 (2)C13—H13B0.9900
C2—H2A0.9500C14—C151.522 (2)
C3—C41.386 (2)C14—H14A0.9900
C3—H3A0.9500C14—H14B0.9900
C4—C51.400 (2)C15—C161.526 (2)
C4—H4A0.9500C15—H15A0.9900
C5—C61.388 (2)C15—H15B0.9900
C5—H5A0.9500C16—C171.522 (2)
C6—C71.5158 (19)C16—H16A0.9900
C7—C121.516 (2)C16—H16B0.9900
C7—C81.5777 (19)C17—H17A0.9900
C7—H7A1.0000C17—H17B0.9900
C8—C181.503 (2)C19—C201.505 (2)
C8—C91.565 (2)C20—H20A0.9800
C9—C101.5623 (19)C20—H20B0.9800
C9—H9A0.9900C20—H20C0.9800
C13—N1—C8114.58 (11)C12—C11—H11A123.1
C13—N1—C17108.78 (11)C10—C11—H11A123.1
C8—N1—C17111.78 (11)C11—C12—C7115.28 (13)
C2—C1—C6120.48 (13)C11—C12—H12A122.4
C2—C1—C10127.35 (13)C7—C12—H12A122.4
C6—C1—C10112.15 (12)N1—C13—C14109.76 (13)
C1—C2—C3119.11 (14)N1—C13—H13A109.7
C1—C2—H2A120.4C14—C13—H13A109.7
C3—C2—H2A120.4N1—C13—H13B109.7
C4—C3—C2120.50 (14)C14—C13—H13B109.7
C4—C3—H3A119.7H13A—C13—H13B108.2
C2—C3—H3A119.7C13—C14—C15112.33 (14)
C3—C4—C5120.39 (14)C13—C14—H14A109.1
C3—C4—H4A119.8C15—C14—H14A109.1
C5—C4—H4A119.8C13—C14—H14B109.1
C6—C5—C4119.20 (14)C15—C14—H14B109.1
C6—C5—H5A120.4H14A—C14—H14B107.9
C4—C5—H5A120.4C14—C15—C16109.56 (14)
C5—C6—C1120.30 (13)C14—C15—H15A109.8
C5—C6—C7125.98 (13)C16—C15—H15A109.8
C1—C6—C7113.71 (12)C14—C15—H15B109.8
C6—C7—C12108.42 (11)C16—C15—H15B109.8
C6—C7—C8106.49 (11)H15A—C15—H15B108.2
C12—C7—C8105.35 (11)C17—C16—C15111.27 (13)
C6—C7—H7A112.1C17—C16—H16A109.4
C12—C7—H7A112.1C15—C16—H16A109.4
C8—C7—H7A112.1C17—C16—H16B109.4
N1—C8—C18110.12 (12)C15—C16—H16B109.4
N1—C8—C9109.95 (11)H16A—C16—H16B108.0
C18—C8—C9109.70 (12)N1—C17—C16111.21 (13)
N1—C8—C7112.40 (11)N1—C17—H17A109.4
C18—C8—C7107.34 (11)C16—C17—H17A109.4
C9—C8—C7107.25 (11)N1—C17—H17B109.4
C10—C9—C8110.66 (11)C16—C17—H17B109.4
C10—C9—H9A109.5H17A—C17—H17B108.0
C8—C9—H9A109.5N2—C18—C8176.05 (17)
C10—C9—H9B109.5O1—C19—C20121.50 (14)
C8—C9—H9B109.5O1—C19—C10120.71 (14)
H9A—C9—H9B108.1C20—C19—C10117.78 (13)
C19—C10—C11115.09 (12)C19—C20—H20A109.5
C19—C10—C1110.12 (11)C19—C20—H20B109.5
C11—C10—C1107.25 (11)H20A—C20—H20B109.5
C19—C10—C9111.91 (12)C19—C20—H20C109.5
C11—C10—C9106.96 (11)H20A—C20—H20C109.5
C1—C10—C9104.91 (11)H20B—C20—H20C109.5
C12—C11—C10113.86 (13)
C6—C1—C2—C30.5 (2)C2—C1—C10—C191.08 (19)
C10—C1—C2—C3177.61 (13)C6—C1—C10—C19179.30 (12)
C1—C2—C3—C40.8 (2)C2—C1—C10—C11127.00 (14)
C2—C3—C4—C51.0 (2)C6—C1—C10—C1154.78 (14)
C3—C4—C5—C60.0 (2)C2—C1—C10—C9119.50 (15)
C4—C5—C6—C11.3 (2)C6—C1—C10—C958.72 (14)
C4—C5—C6—C7178.88 (12)C8—C9—C10—C19179.61 (12)
C2—C1—C6—C51.5 (2)C8—C9—C10—C1152.71 (15)
C10—C1—C6—C5176.85 (12)C8—C9—C10—C160.99 (14)
C2—C1—C6—C7178.62 (12)C19—C10—C11—C12176.97 (13)
C10—C1—C6—C73.02 (15)C1—C10—C11—C1254.08 (16)
C5—C6—C7—C12130.26 (14)C9—C10—C11—C1258.03 (16)
C1—C6—C7—C1249.88 (15)C10—C11—C12—C70.41 (18)
C5—C6—C7—C8116.82 (14)C6—C7—C12—C1152.48 (16)
C1—C6—C7—C863.05 (14)C8—C7—C12—C1161.20 (16)
C13—N1—C8—C1868.57 (15)C8—N1—C13—C14171.92 (12)
C17—N1—C8—C1855.77 (15)C17—N1—C13—C1462.16 (15)
C13—N1—C8—C9170.45 (11)N1—C13—C14—C1558.72 (18)
C17—N1—C8—C965.22 (14)C13—C14—C15—C1652.25 (19)
C13—N1—C8—C751.05 (15)C14—C15—C16—C1750.80 (18)
C17—N1—C8—C7175.39 (11)C13—N1—C17—C1662.15 (15)
C6—C7—C8—N165.26 (14)C8—N1—C17—C16170.33 (12)
C12—C7—C8—N1179.72 (11)C15—C16—C17—N157.00 (16)
C6—C7—C8—C18173.51 (12)C11—C10—C19—O1140.96 (14)
C12—C7—C8—C1858.49 (14)C1—C10—C19—O197.69 (16)
C6—C7—C8—C955.69 (14)C9—C10—C19—O118.59 (19)
C12—C7—C8—C959.33 (14)C11—C10—C19—C2040.53 (18)
N1—C8—C9—C10126.82 (12)C1—C10—C19—C2080.82 (15)
C18—C8—C9—C10111.94 (13)C9—C10—C19—C20162.90 (13)
C7—C8—C9—C104.33 (15)
 

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