Download citation
Download citation
link to html
In the title mol­ecule, C20H29NO, the cyclo­butane ring is puckered, with a dihedral angle of 19.8 (3)° between the two planes. The pyrrolidine ring adopts an envelope conformation. There are intermolecular C—H...O and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804019002/ob6401sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804019002/ob6401Isup2.hkl
Contains datablock I

CCDC reference: 251717

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.068
  • wR factor = 0.194
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.735 Test value = 0.600 DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.10 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.74 e/A   3 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B .. O1 .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A .. O1 .. 2.69 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9B .. CG3 .. 3.05 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A .. CG3 .. 2.96 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C9 .. CG3 .. 3.99 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-(3-Mesityl-3-methylcyclobutyl)-2-(pyrrolidin-1-yl)ethan-1-one top
Crystal data top
C20H29NODx = 1.120 Mg m3
Mr = 299.44Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42/nCell parameters from 18614 reflections
Hall symbol: -P 4bcθ = 1.4–26.0°
a = 21.2110 (9) ŵ = 0.07 mm1
c = 7.8940 (4) ÅT = 293 K
V = 3551.6 (3) Å3Prism, yellow
Z = 80.42 × 0.29 × 0.20 mm
F(000) = 1312
Data collection top
Stoe IPDS-II
diffractometer
1642 reflections with I > 2σ(I)
Radiation source: sealed X-ray tubeRint = 0.068
Plane graphite monochromatorθmax = 26.0°, θmin = 1.4°
Detector resolution: 6.67 pixels mm-1h = 2626
ω scansk = 2626
23972 measured reflectionsl = 98
3390 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.194 w = 1/[σ2(Fo2) + (0.0947P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3390 reflectionsΔρmax = 0.74 e Å3
202 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0042 (12)
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
O10.01735 (10)0.47663 (10)0.2651 (3)0.0611 (7)
N10.10207 (11)0.61478 (11)0.3020 (4)0.0556 (8)
C10.13574 (19)0.59939 (18)0.1550 (6)0.0725 (12)
H1A0.10730.59190.06090.087*
H1B0.16120.56200.17260.087*
C20.17553 (18)0.6543 (2)0.1226 (7)0.0885 (15)
H2A0.15570.68210.04080.106*
H2B0.21620.64140.07880.106*
C30.18316 (17)0.68755 (18)0.2922 (6)0.0772 (13)
H3A0.22750.69230.31970.093*
H3B0.16390.72900.28850.093*
C40.15090 (16)0.64699 (17)0.4221 (6)0.0721 (12)
H4A0.13070.67180.50980.087*
H4B0.17950.61680.47310.087*
C50.03070 (14)0.57584 (15)0.2227 (5)0.0545 (10)
H50.01510.60620.13910.065*
C60.06678 (14)0.60881 (14)0.3649 (5)0.0500 (9)
H6A0.05830.65370.37220.060*
H6B0.06180.58880.47450.060*
C70.13078 (13)0.59287 (13)0.2759 (4)0.0438 (8)
C80.09309 (14)0.54568 (16)0.1646 (5)0.0521 (9)
H8A0.09780.50210.19950.063*
H8B0.10110.55030.04420.063*
C90.07508 (16)0.56114 (17)0.3900 (5)0.0641 (10)
H9A0.05850.57440.49880.077*
H9B0.10740.52960.40980.077*
C100.02067 (15)0.53218 (16)0.2794 (6)0.0664 (11)
C110.15517 (15)0.64903 (15)0.1724 (5)0.0572 (10)
H11A0.12190.66500.10220.086*
H11B0.16930.68160.24790.086*
H11C0.18970.63560.10240.086*
C120.18235 (12)0.56590 (13)0.3894 (4)0.0376 (7)
C130.22210 (12)0.51696 (13)0.3304 (4)0.0367 (7)
C140.26606 (12)0.48986 (13)0.4398 (4)0.0387 (7)
H140.29130.45720.40000.046*
C150.27349 (13)0.50965 (13)0.6041 (4)0.0412 (8)
C160.23747 (13)0.55985 (14)0.6577 (4)0.0423 (8)
H160.24300.57500.76730.051*
C170.19308 (13)0.58874 (13)0.5540 (4)0.0408 (8)
C180.22045 (15)0.49112 (16)0.1525 (4)0.0518 (9)
H18A0.18870.51280.08840.078*
H18B0.26080.49720.09980.078*
H18C0.21080.44690.15600.078*
C190.32105 (14)0.47823 (16)0.7211 (5)0.0537 (9)
H19A0.31000.48680.83680.081*
H19B0.32070.43350.70210.081*
H19C0.36240.49460.69820.081*
C200.15962 (16)0.64603 (16)0.6271 (5)0.0603 (10)
H20A0.18640.66610.70900.090*
H20B0.15020.67520.53770.090*
H20C0.12120.63300.68080.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0586 (14)0.0445 (14)0.080 (2)0.0028 (10)0.0041 (13)0.0026 (12)
N10.0336 (13)0.0410 (14)0.092 (3)0.0030 (11)0.0088 (14)0.0061 (14)
C10.070 (2)0.069 (2)0.078 (3)0.010 (2)0.016 (2)0.009 (2)
C20.053 (2)0.090 (3)0.123 (4)0.001 (2)0.010 (2)0.022 (3)
C30.051 (2)0.063 (2)0.117 (4)0.0159 (17)0.003 (2)0.011 (2)
C40.048 (2)0.056 (2)0.112 (4)0.0006 (16)0.004 (2)0.001 (2)
C50.0394 (16)0.0500 (18)0.074 (3)0.0049 (14)0.0064 (16)0.0134 (17)
C60.0421 (16)0.0454 (17)0.063 (3)0.0071 (13)0.0036 (16)0.0102 (16)
C70.0402 (15)0.0443 (16)0.047 (2)0.0026 (13)0.0023 (14)0.0052 (14)
C80.0408 (16)0.062 (2)0.053 (2)0.0056 (14)0.0102 (15)0.0031 (17)
C90.060 (2)0.065 (2)0.067 (3)0.0021 (17)0.0082 (19)0.0113 (19)
C100.0424 (18)0.0439 (19)0.113 (4)0.0050 (14)0.0090 (19)0.011 (2)
C110.0478 (18)0.0558 (19)0.068 (3)0.0067 (15)0.0026 (17)0.0194 (18)
C120.0353 (14)0.0377 (15)0.040 (2)0.0019 (11)0.0021 (13)0.0025 (13)
C130.0329 (14)0.0411 (15)0.036 (2)0.0004 (12)0.0002 (13)0.0005 (13)
C140.0339 (14)0.0402 (15)0.042 (2)0.0003 (12)0.0007 (13)0.0019 (13)
C150.0351 (15)0.0473 (17)0.041 (2)0.0062 (12)0.0023 (13)0.0046 (14)
C160.0414 (16)0.0488 (17)0.037 (2)0.0064 (14)0.0010 (14)0.0053 (14)
C170.0366 (15)0.0396 (15)0.046 (2)0.0006 (12)0.0037 (14)0.0021 (14)
C180.0475 (18)0.063 (2)0.045 (2)0.0058 (15)0.0011 (15)0.0086 (16)
C190.0478 (18)0.065 (2)0.048 (2)0.0020 (15)0.0109 (16)0.0066 (17)
C200.061 (2)0.057 (2)0.064 (3)0.0095 (16)0.0026 (18)0.0182 (18)
Geometric parameters (Å, º) top
O1—C101.186 (4)C9—C101.572 (5)
N1—C11.401 (5)C9—H9A0.9700
N1—C91.450 (4)C9—H9B0.9700
N1—C41.561 (5)C11—H11A0.9600
C1—C21.461 (6)C11—H11B0.9600
C1—H1A0.9700C11—H11C0.9600
C1—H1B0.9700C12—C171.405 (4)
C2—C31.522 (6)C12—C131.416 (4)
C2—H2A0.9700C13—C141.395 (4)
C2—H2B0.9700C13—C181.508 (4)
C3—C41.503 (6)C14—C151.373 (4)
C3—H3A0.9700C14—H140.9300
C3—H3B0.9700C15—C161.377 (4)
C4—H4A0.9700C15—C191.521 (4)
C4—H4B0.9700C16—C171.390 (4)
C5—C101.498 (5)C16—H160.9300
C5—C61.527 (5)C17—C201.521 (4)
C5—C81.540 (4)C18—H18A0.9600
C5—H50.9800C18—H18B0.9600
C6—C71.565 (4)C18—H18C0.9600
C6—H6A0.9700C19—H19A0.9600
C6—H6B0.9700C19—H19B0.9600
C7—C121.525 (4)C19—H19C0.9600
C7—C111.534 (4)C20—H20A0.9600
C7—C81.554 (4)C20—H20B0.9600
C8—H8A0.9700C20—H20C0.9600
C8—H8B0.9700
C1—N1—C9114.5 (3)N1—C9—C10109.3 (3)
C1—N1—C4105.5 (3)N1—C9—H9A109.8
C9—N1—C4108.3 (3)C10—C9—H9A109.8
N1—C1—C2104.7 (3)N1—C9—H9B109.8
N1—C1—H1A110.8C10—C9—H9B109.8
C2—C1—H1A110.8H9A—C9—H9B108.3
N1—C1—H1B110.8O1—C10—C5122.9 (3)
C2—C1—H1B110.8O1—C10—C9119.0 (3)
H1A—C1—H1B108.9C5—C10—C9117.3 (3)
C1—C2—C3106.1 (4)C7—C11—H11A109.5
C1—C2—H2A110.5C7—C11—H11B109.5
C3—C2—H2A110.5H11A—C11—H11B109.5
C1—C2—H2B110.5C7—C11—H11C109.5
C3—C2—H2B110.5H11A—C11—H11C109.5
H2A—C2—H2B108.7H11B—C11—H11C109.5
C4—C3—C2106.7 (3)C17—C12—C13117.4 (3)
C4—C3—H3A110.4C17—C12—C7122.0 (3)
C2—C3—H3A110.4C13—C12—C7120.6 (3)
C4—C3—H3B110.4C14—C13—C12119.7 (3)
C2—C3—H3B110.4C14—C13—C18116.3 (3)
H3A—C3—H3B108.6C12—C13—C18124.0 (3)
C3—C4—N198.0 (3)C15—C14—C13122.4 (3)
C3—C4—H4A112.2C15—C14—H14118.8
N1—C4—H4A112.2C13—C14—H14118.8
C3—C4—H4B112.2C14—C15—C16117.6 (3)
N1—C4—H4B112.2C14—C15—C19121.0 (3)
H4A—C4—H4B109.8C16—C15—C19121.4 (3)
C10—C5—C6115.3 (3)C15—C16—C17122.4 (3)
C10—C5—C8117.2 (3)C15—C16—H16118.8
C6—C5—C888.8 (2)C17—C16—H16118.8
C10—C5—H5111.3C16—C17—C12120.2 (3)
C6—C5—H5111.3C16—C17—C20116.4 (3)
C8—C5—H5111.3C12—C17—C20123.4 (3)
C5—C6—C790.4 (3)C13—C18—H18A109.5
C5—C6—H6A113.6C13—C18—H18B109.5
C7—C6—H6A113.6H18A—C18—H18B109.5
C5—C6—H6B113.6C13—C18—H18C109.5
C7—C6—H6B113.6H18A—C18—H18C109.5
H6A—C6—H6B110.9H18B—C18—H18C109.5
C12—C7—C11111.2 (2)C15—C19—H19A109.5
C12—C7—C8117.4 (2)C15—C19—H19B109.5
C11—C7—C8111.9 (3)H19A—C19—H19B109.5
C12—C7—C6116.1 (3)C15—C19—H19C109.5
C11—C7—C6111.3 (2)H19A—C19—H19C109.5
C8—C7—C686.9 (2)H19B—C19—H19C109.5
C5—C8—C790.3 (3)C17—C20—H20A109.5
C5—C8—H8A113.6C17—C20—H20B109.5
C7—C8—H8A113.6H20A—C20—H20B109.5
C5—C8—H8B113.6C17—C20—H20C109.5
C7—C8—H8B113.6H20A—C20—H20C109.5
H8A—C8—H8B110.9H20B—C20—H20C109.5
C9—N1—C1—C2161.0 (3)N1—C9—C10—C554.1 (4)
C4—N1—C1—C241.9 (4)C11—C7—C12—C1788.4 (3)
N1—C1—C2—C323.5 (4)C8—C7—C12—C17141.0 (3)
C1—C2—C3—C44.3 (4)C6—C7—C12—C1740.2 (4)
C2—C3—C4—N126.8 (4)C11—C7—C12—C1390.6 (3)
C1—N1—C4—C342.8 (3)C8—C7—C12—C1340.0 (4)
C9—N1—C4—C3165.8 (3)C6—C7—C12—C13140.7 (3)
C10—C5—C6—C7134.1 (3)C17—C12—C13—C145.4 (4)
C8—C5—C6—C714.3 (2)C7—C12—C13—C14175.5 (2)
C5—C6—C7—C12133.3 (3)C17—C12—C13—C18174.6 (3)
C5—C6—C7—C1198.1 (3)C7—C12—C13—C184.5 (4)
C5—C6—C7—C814.2 (2)C12—C13—C14—C151.3 (4)
C10—C5—C8—C7132.5 (3)C18—C13—C14—C15178.7 (3)
C6—C5—C8—C714.4 (3)C13—C14—C15—C162.7 (4)
C12—C7—C8—C5132.0 (3)C13—C14—C15—C19178.8 (3)
C11—C7—C8—C597.7 (3)C14—C15—C16—C172.5 (4)
C6—C7—C8—C514.1 (2)C19—C15—C16—C17179.1 (3)
C1—N1—C9—C1068.6 (4)C15—C16—C17—C121.7 (4)
C4—N1—C9—C10174.1 (3)C15—C16—C17—C20176.5 (3)
C6—C5—C10—O1110.3 (4)C13—C12—C17—C165.6 (4)
C8—C5—C10—O17.7 (6)C7—C12—C17—C16175.3 (3)
C6—C5—C10—C958.9 (4)C13—C12—C17—C20172.5 (3)
C8—C5—C10—C9161.4 (3)C7—C12—C17—C206.5 (4)
N1—C9—C10—O1136.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6B···O1i0.972.653.594 (4)164
C9—H9A···O1i0.972.693.450 (5)136
C9—H9B···Cg3ii0.973.053.994 (4)165
C11—H11A···Cg3iii0.962.963.818 (3)149
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+2; (iii) y1/2, x, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds