In the title molecule, C
20H
29NO, 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
CCDC reference: 251717
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C20H29NO | Dx = 1.120 Mg m−3 |
Mr = 299.44 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P42/n | Cell parameters from 18614 reflections |
Hall symbol: -P 4bc | θ = 1.4–26.0° |
a = 21.2110 (9) Å | µ = 0.07 mm−1 |
c = 7.8940 (4) Å | T = 293 K |
V = 3551.6 (3) Å3 | Prism, yellow |
Z = 8 | 0.42 × 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 tube | Rint = 0.068 |
Plane graphite monochromator | θmax = 26.0°, θmin = 1.4° |
Detector resolution: 6.67 pixels mm-1 | h = −26→26 |
ω scans | k = −26→26 |
23972 measured reflections | l = −9→8 |
3390 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.068 | H-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 reflections | Δρmax = 0.74 e Å−3 |
202 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.01735 (10) | 0.47663 (10) | 0.2651 (3) | 0.0611 (7) | |
N1 | 0.10207 (11) | 0.61478 (11) | 0.3020 (4) | 0.0556 (8) | |
C1 | 0.13574 (19) | 0.59939 (18) | 0.1550 (6) | 0.0725 (12) | |
H1A | 0.1073 | 0.5919 | 0.0609 | 0.087* | |
H1B | 0.1612 | 0.5620 | 0.1726 | 0.087* | |
C2 | 0.17553 (18) | 0.6543 (2) | 0.1226 (7) | 0.0885 (15) | |
H2A | 0.1557 | 0.6821 | 0.0408 | 0.106* | |
H2B | 0.2162 | 0.6414 | 0.0788 | 0.106* | |
C3 | 0.18316 (17) | 0.68755 (18) | 0.2922 (6) | 0.0772 (13) | |
H3A | 0.2275 | 0.6923 | 0.3197 | 0.093* | |
H3B | 0.1639 | 0.7290 | 0.2885 | 0.093* | |
C4 | 0.15090 (16) | 0.64699 (17) | 0.4221 (6) | 0.0721 (12) | |
H4A | 0.1307 | 0.6718 | 0.5098 | 0.087* | |
H4B | 0.1795 | 0.6168 | 0.4731 | 0.087* | |
C5 | −0.03070 (14) | 0.57584 (15) | 0.2227 (5) | 0.0545 (10) | |
H5 | −0.0151 | 0.6062 | 0.1391 | 0.065* | |
C6 | −0.06678 (14) | 0.60881 (14) | 0.3649 (5) | 0.0500 (9) | |
H6A | −0.0583 | 0.6537 | 0.3722 | 0.060* | |
H6B | −0.0618 | 0.5888 | 0.4745 | 0.060* | |
C7 | −0.13078 (13) | 0.59287 (13) | 0.2759 (4) | 0.0438 (8) | |
C8 | −0.09309 (14) | 0.54568 (16) | 0.1646 (5) | 0.0521 (9) | |
H8A | −0.0978 | 0.5021 | 0.1995 | 0.063* | |
H8B | −0.1011 | 0.5503 | 0.0442 | 0.063* | |
C9 | 0.07508 (16) | 0.56114 (17) | 0.3900 (5) | 0.0641 (10) | |
H9A | 0.0585 | 0.5744 | 0.4988 | 0.077* | |
H9B | 0.1074 | 0.5296 | 0.4098 | 0.077* | |
C10 | 0.02067 (15) | 0.53218 (16) | 0.2794 (6) | 0.0664 (11) | |
C11 | −0.15517 (15) | 0.64903 (15) | 0.1724 (5) | 0.0572 (10) | |
H11A | −0.1219 | 0.6650 | 0.1022 | 0.086* | |
H11B | −0.1693 | 0.6816 | 0.2479 | 0.086* | |
H11C | −0.1897 | 0.6356 | 0.1024 | 0.086* | |
C12 | −0.18235 (12) | 0.56590 (13) | 0.3894 (4) | 0.0376 (7) | |
C13 | −0.22210 (12) | 0.51696 (13) | 0.3304 (4) | 0.0367 (7) | |
C14 | −0.26606 (12) | 0.48986 (13) | 0.4398 (4) | 0.0387 (7) | |
H14 | −0.2913 | 0.4572 | 0.4000 | 0.046* | |
C15 | −0.27349 (13) | 0.50965 (13) | 0.6041 (4) | 0.0412 (8) | |
C16 | −0.23747 (13) | 0.55985 (14) | 0.6577 (4) | 0.0423 (8) | |
H16 | −0.2430 | 0.5750 | 0.7673 | 0.051* | |
C17 | −0.19308 (13) | 0.58874 (13) | 0.5540 (4) | 0.0408 (8) | |
C18 | −0.22045 (15) | 0.49112 (16) | 0.1525 (4) | 0.0518 (9) | |
H18A | −0.1887 | 0.5128 | 0.0884 | 0.078* | |
H18B | −0.2608 | 0.4972 | 0.0998 | 0.078* | |
H18C | −0.2108 | 0.4469 | 0.1560 | 0.078* | |
C19 | −0.32105 (14) | 0.47823 (16) | 0.7211 (5) | 0.0537 (9) | |
H19A | −0.3100 | 0.4868 | 0.8368 | 0.081* | |
H19B | −0.3207 | 0.4335 | 0.7021 | 0.081* | |
H19C | −0.3624 | 0.4946 | 0.6982 | 0.081* | |
C20 | −0.15962 (16) | 0.64603 (16) | 0.6271 (5) | 0.0603 (10) | |
H20A | −0.1864 | 0.6661 | 0.7090 | 0.090* | |
H20B | −0.1502 | 0.6752 | 0.5377 | 0.090* | |
H20C | −0.1212 | 0.6330 | 0.6808 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0586 (14) | 0.0445 (14) | 0.080 (2) | −0.0028 (10) | 0.0041 (13) | 0.0026 (12) |
N1 | 0.0336 (13) | 0.0410 (14) | 0.092 (3) | −0.0030 (11) | 0.0088 (14) | 0.0061 (14) |
C1 | 0.070 (2) | 0.069 (2) | 0.078 (3) | 0.010 (2) | 0.016 (2) | 0.009 (2) |
C2 | 0.053 (2) | 0.090 (3) | 0.123 (4) | 0.001 (2) | 0.010 (2) | −0.022 (3) |
C3 | 0.051 (2) | 0.063 (2) | 0.117 (4) | −0.0159 (17) | 0.003 (2) | −0.011 (2) |
C4 | 0.048 (2) | 0.056 (2) | 0.112 (4) | 0.0006 (16) | 0.004 (2) | −0.001 (2) |
C5 | 0.0394 (16) | 0.0500 (18) | 0.074 (3) | −0.0049 (14) | 0.0064 (16) | 0.0134 (17) |
C6 | 0.0421 (16) | 0.0454 (17) | 0.063 (3) | −0.0071 (13) | −0.0036 (16) | 0.0102 (16) |
C7 | 0.0402 (15) | 0.0443 (16) | 0.047 (2) | −0.0026 (13) | −0.0023 (14) | 0.0052 (14) |
C8 | 0.0408 (16) | 0.062 (2) | 0.053 (2) | −0.0056 (14) | 0.0102 (15) | 0.0031 (17) |
C9 | 0.060 (2) | 0.065 (2) | 0.067 (3) | 0.0021 (17) | 0.0082 (19) | 0.0113 (19) |
C10 | 0.0424 (18) | 0.0439 (19) | 0.113 (4) | −0.0050 (14) | 0.0090 (19) | 0.011 (2) |
C11 | 0.0478 (18) | 0.0558 (19) | 0.068 (3) | −0.0067 (15) | −0.0026 (17) | 0.0194 (18) |
C12 | 0.0353 (14) | 0.0377 (15) | 0.040 (2) | 0.0019 (11) | −0.0021 (13) | 0.0025 (13) |
C13 | 0.0329 (14) | 0.0411 (15) | 0.036 (2) | −0.0004 (12) | −0.0002 (13) | −0.0005 (13) |
C14 | 0.0339 (14) | 0.0402 (15) | 0.042 (2) | 0.0003 (12) | 0.0007 (13) | −0.0019 (13) |
C15 | 0.0351 (15) | 0.0473 (17) | 0.041 (2) | 0.0062 (12) | 0.0023 (13) | 0.0046 (14) |
C16 | 0.0414 (16) | 0.0488 (17) | 0.037 (2) | 0.0064 (14) | −0.0010 (14) | −0.0053 (14) |
C17 | 0.0366 (15) | 0.0396 (15) | 0.046 (2) | 0.0006 (12) | −0.0037 (14) | −0.0021 (14) |
C18 | 0.0475 (18) | 0.063 (2) | 0.045 (2) | −0.0058 (15) | 0.0011 (15) | −0.0086 (16) |
C19 | 0.0478 (18) | 0.065 (2) | 0.048 (2) | −0.0020 (15) | 0.0109 (16) | 0.0066 (17) |
C20 | 0.061 (2) | 0.057 (2) | 0.064 (3) | −0.0095 (16) | −0.0026 (18) | −0.0182 (18) |
Geometric parameters (Å, º) top
O1—C10 | 1.186 (4) | C9—C10 | 1.572 (5) |
N1—C1 | 1.401 (5) | C9—H9A | 0.9700 |
N1—C9 | 1.450 (4) | C9—H9B | 0.9700 |
N1—C4 | 1.561 (5) | C11—H11A | 0.9600 |
C1—C2 | 1.461 (6) | C11—H11B | 0.9600 |
C1—H1A | 0.9700 | C11—H11C | 0.9600 |
C1—H1B | 0.9700 | C12—C17 | 1.405 (4) |
C2—C3 | 1.522 (6) | C12—C13 | 1.416 (4) |
C2—H2A | 0.9700 | C13—C14 | 1.395 (4) |
C2—H2B | 0.9700 | C13—C18 | 1.508 (4) |
C3—C4 | 1.503 (6) | C14—C15 | 1.373 (4) |
C3—H3A | 0.9700 | C14—H14 | 0.9300 |
C3—H3B | 0.9700 | C15—C16 | 1.377 (4) |
C4—H4A | 0.9700 | C15—C19 | 1.521 (4) |
C4—H4B | 0.9700 | C16—C17 | 1.390 (4) |
C5—C10 | 1.498 (5) | C16—H16 | 0.9300 |
C5—C6 | 1.527 (5) | C17—C20 | 1.521 (4) |
C5—C8 | 1.540 (4) | C18—H18A | 0.9600 |
C5—H5 | 0.9800 | C18—H18B | 0.9600 |
C6—C7 | 1.565 (4) | C18—H18C | 0.9600 |
C6—H6A | 0.9700 | C19—H19A | 0.9600 |
C6—H6B | 0.9700 | C19—H19B | 0.9600 |
C7—C12 | 1.525 (4) | C19—H19C | 0.9600 |
C7—C11 | 1.534 (4) | C20—H20A | 0.9600 |
C7—C8 | 1.554 (4) | C20—H20B | 0.9600 |
C8—H8A | 0.9700 | C20—H20C | 0.9600 |
C8—H8B | 0.9700 | | |
| | | |
C1—N1—C9 | 114.5 (3) | N1—C9—C10 | 109.3 (3) |
C1—N1—C4 | 105.5 (3) | N1—C9—H9A | 109.8 |
C9—N1—C4 | 108.3 (3) | C10—C9—H9A | 109.8 |
N1—C1—C2 | 104.7 (3) | N1—C9—H9B | 109.8 |
N1—C1—H1A | 110.8 | C10—C9—H9B | 109.8 |
C2—C1—H1A | 110.8 | H9A—C9—H9B | 108.3 |
N1—C1—H1B | 110.8 | O1—C10—C5 | 122.9 (3) |
C2—C1—H1B | 110.8 | O1—C10—C9 | 119.0 (3) |
H1A—C1—H1B | 108.9 | C5—C10—C9 | 117.3 (3) |
C1—C2—C3 | 106.1 (4) | C7—C11—H11A | 109.5 |
C1—C2—H2A | 110.5 | C7—C11—H11B | 109.5 |
C3—C2—H2A | 110.5 | H11A—C11—H11B | 109.5 |
C1—C2—H2B | 110.5 | C7—C11—H11C | 109.5 |
C3—C2—H2B | 110.5 | H11A—C11—H11C | 109.5 |
H2A—C2—H2B | 108.7 | H11B—C11—H11C | 109.5 |
C4—C3—C2 | 106.7 (3) | C17—C12—C13 | 117.4 (3) |
C4—C3—H3A | 110.4 | C17—C12—C7 | 122.0 (3) |
C2—C3—H3A | 110.4 | C13—C12—C7 | 120.6 (3) |
C4—C3—H3B | 110.4 | C14—C13—C12 | 119.7 (3) |
C2—C3—H3B | 110.4 | C14—C13—C18 | 116.3 (3) |
H3A—C3—H3B | 108.6 | C12—C13—C18 | 124.0 (3) |
C3—C4—N1 | 98.0 (3) | C15—C14—C13 | 122.4 (3) |
C3—C4—H4A | 112.2 | C15—C14—H14 | 118.8 |
N1—C4—H4A | 112.2 | C13—C14—H14 | 118.8 |
C3—C4—H4B | 112.2 | C14—C15—C16 | 117.6 (3) |
N1—C4—H4B | 112.2 | C14—C15—C19 | 121.0 (3) |
H4A—C4—H4B | 109.8 | C16—C15—C19 | 121.4 (3) |
C10—C5—C6 | 115.3 (3) | C15—C16—C17 | 122.4 (3) |
C10—C5—C8 | 117.2 (3) | C15—C16—H16 | 118.8 |
C6—C5—C8 | 88.8 (2) | C17—C16—H16 | 118.8 |
C10—C5—H5 | 111.3 | C16—C17—C12 | 120.2 (3) |
C6—C5—H5 | 111.3 | C16—C17—C20 | 116.4 (3) |
C8—C5—H5 | 111.3 | C12—C17—C20 | 123.4 (3) |
C5—C6—C7 | 90.4 (3) | C13—C18—H18A | 109.5 |
C5—C6—H6A | 113.6 | C13—C18—H18B | 109.5 |
C7—C6—H6A | 113.6 | H18A—C18—H18B | 109.5 |
C5—C6—H6B | 113.6 | C13—C18—H18C | 109.5 |
C7—C6—H6B | 113.6 | H18A—C18—H18C | 109.5 |
H6A—C6—H6B | 110.9 | H18B—C18—H18C | 109.5 |
C12—C7—C11 | 111.2 (2) | C15—C19—H19A | 109.5 |
C12—C7—C8 | 117.4 (2) | C15—C19—H19B | 109.5 |
C11—C7—C8 | 111.9 (3) | H19A—C19—H19B | 109.5 |
C12—C7—C6 | 116.1 (3) | C15—C19—H19C | 109.5 |
C11—C7—C6 | 111.3 (2) | H19A—C19—H19C | 109.5 |
C8—C7—C6 | 86.9 (2) | H19B—C19—H19C | 109.5 |
C5—C8—C7 | 90.3 (3) | C17—C20—H20A | 109.5 |
C5—C8—H8A | 113.6 | C17—C20—H20B | 109.5 |
C7—C8—H8A | 113.6 | H20A—C20—H20B | 109.5 |
C5—C8—H8B | 113.6 | C17—C20—H20C | 109.5 |
C7—C8—H8B | 113.6 | H20A—C20—H20C | 109.5 |
H8A—C8—H8B | 110.9 | H20B—C20—H20C | 109.5 |
| | | |
C9—N1—C1—C2 | −161.0 (3) | N1—C9—C10—C5 | −54.1 (4) |
C4—N1—C1—C2 | −41.9 (4) | C11—C7—C12—C17 | −88.4 (3) |
N1—C1—C2—C3 | 23.5 (4) | C8—C7—C12—C17 | 141.0 (3) |
C1—C2—C3—C4 | 4.3 (4) | C6—C7—C12—C17 | 40.2 (4) |
C2—C3—C4—N1 | −26.8 (4) | C11—C7—C12—C13 | 90.6 (3) |
C1—N1—C4—C3 | 42.8 (3) | C8—C7—C12—C13 | −40.0 (4) |
C9—N1—C4—C3 | 165.8 (3) | C6—C7—C12—C13 | −140.7 (3) |
C10—C5—C6—C7 | −134.1 (3) | C17—C12—C13—C14 | −5.4 (4) |
C8—C5—C6—C7 | −14.3 (2) | C7—C12—C13—C14 | 175.5 (2) |
C5—C6—C7—C12 | 133.3 (3) | C17—C12—C13—C18 | 174.6 (3) |
C5—C6—C7—C11 | −98.1 (3) | C7—C12—C13—C18 | −4.5 (4) |
C5—C6—C7—C8 | 14.2 (2) | C12—C13—C14—C15 | 1.3 (4) |
C10—C5—C8—C7 | 132.5 (3) | C18—C13—C14—C15 | −178.7 (3) |
C6—C5—C8—C7 | 14.4 (3) | C13—C14—C15—C16 | 2.7 (4) |
C12—C7—C8—C5 | −132.0 (3) | C13—C14—C15—C19 | −178.8 (3) |
C11—C7—C8—C5 | 97.7 (3) | C14—C15—C16—C17 | −2.5 (4) |
C6—C7—C8—C5 | −14.1 (2) | C19—C15—C16—C17 | 179.1 (3) |
C1—N1—C9—C10 | −68.6 (4) | C15—C16—C17—C12 | −1.7 (4) |
C4—N1—C9—C10 | 174.1 (3) | C15—C16—C17—C20 | 176.5 (3) |
C6—C5—C10—O1 | 110.3 (4) | C13—C12—C17—C16 | 5.6 (4) |
C8—C5—C10—O1 | 7.7 (6) | C7—C12—C17—C16 | −175.3 (3) |
C6—C5—C10—C9 | −58.9 (4) | C13—C12—C17—C20 | −172.5 (3) |
C8—C5—C10—C9 | −161.4 (3) | C7—C12—C17—C20 | 6.5 (4) |
N1—C9—C10—O1 | 136.3 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6B···O1i | 0.97 | 2.65 | 3.594 (4) | 164 |
C9—H9A···O1i | 0.97 | 2.69 | 3.450 (5) | 136 |
C9—H9B···Cg3ii | 0.97 | 3.05 | 3.994 (4) | 165 |
C11—H11A···Cg3iii | 0.96 | 2.96 | 3.818 (3) | 149 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+2; (iii) −y−1/2, x, −z+1/2. |