Download citation
Download citation
link to html
In the title mol­ecule, C31H28N2O2, the piperidinone ring adopts the usual twist-boat conformation. The aryl rings at positions 2 and 3 are axial and those at positions 5 and 6 are equatorial. In the crystal structure, there are no hydrogen bonds nor are there any significant π...π stacking inter­actions and, apart from two weak C—H...π(arene) inter­actions, mol­ecules are separated by normal van der Waals distances.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026031/lh2076sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026031/lh2076Isup2.hkl
Contains datablock I

CCDC reference: 618260

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.049
  • wR factor = 0.152
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 221.00 A   3
Author Response: see _publ_section_exptl_refinement (Experimental)

Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C31 - C36 .. 5.51 su PLAT432_ALERT_2_C Short Inter X...Y Contact C53 .. C53 .. 3.19 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius,1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2,6-bis(4-methylphenyl)-1-nitroso-3,5-diphenyltetrahydro-4(1H)-pyridinone top
Crystal data top
C31H28N2O2Z = 2
Mr = 460.55F(000) = 488
Triclinic, P1Dx = 1.100 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 10.4373 (13) ÅCell parameters from 4893 reflections
b = 12.0428 (13) Åθ = 11.3–13.5°
c = 12.6808 (14) ŵ = 0.07 mm1
α = 67.947 (12)°T = 293 K
β = 71.053 (9)°Block, colourless
γ = 78.081 (12)°0.26 × 0.18 × 0.12 mm
V = 1390.7 (3) Å3
Data collection top
Nonius MACH3 4 circle
diffractometer
2525 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω scansh = 112
Absorption correction: ψ scan
(North et al., 1968)
k = 1414
Tmin = 0.985, Tmax = 0.992l = 1415
5778 measured reflections3 standard reflections every 60 min
4893 independent reflections intensity decay: none
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.0769P)2 + 0.0251P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
4893 reflectionsΔρmax = 0.16 e Å3
319 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (3)
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
C20.3321 (2)0.8353 (2)0.8445 (2)0.0470 (6)
H20.24930.82200.91050.056*
C610.6908 (2)0.8032 (2)0.8249 (2)0.0454 (6)
C60.5694 (2)0.8960 (2)0.8135 (2)0.0458 (6)
H60.58170.96020.83820.055*
C30.3019 (2)0.9557 (2)0.7498 (2)0.0445 (6)
H30.25760.93580.70270.053*
C210.3661 (2)0.7246 (2)0.8070 (2)0.0473 (6)
C660.7027 (3)0.6971 (2)0.8025 (3)0.0602 (8)
H660.63110.67870.78530.072*
C510.6787 (3)1.0353 (2)0.6125 (2)0.0498 (7)
C50.5671 (2)0.9530 (2)0.6827 (2)0.0448 (6)
H50.58950.88650.65110.054*
C240.4355 (3)0.5128 (2)0.7483 (3)0.0620 (8)
C310.2018 (3)1.0448 (2)0.8011 (2)0.0472 (6)
C320.0662 (3)1.0545 (3)0.8072 (3)0.0666 (8)
H320.03601.00440.78130.080*
C230.4024 (3)0.5088 (2)0.8649 (3)0.0644 (8)
H230.40320.43460.92460.077*
C650.8191 (3)0.6177 (3)0.8052 (3)0.0639 (8)
H650.82300.54610.79190.077*
C640.9296 (3)0.6423 (3)0.8271 (2)0.0572 (7)
C250.4312 (3)0.6247 (2)0.6631 (3)0.0603 (7)
H250.45210.63000.58440.072*
C220.3686 (3)0.6122 (2)0.8934 (2)0.0568 (7)
H220.34690.60680.97220.068*
C560.6816 (3)1.1356 (3)0.6395 (3)0.0723 (9)
H560.61441.15170.70260.087*
C360.2422 (3)1.1207 (3)0.8407 (2)0.0644 (8)
H360.33311.11510.83870.077*
C40.4287 (3)1.0130 (2)0.6639 (2)0.0486 (6)
C630.9179 (3)0.7476 (3)0.8488 (3)0.0668 (8)
H630.99060.76640.86430.080*
C260.3969 (3)0.7287 (2)0.6912 (2)0.0500 (7)
H260.39440.80270.63150.060*
C520.7803 (3)1.0131 (3)0.5189 (2)0.0569 (7)
H520.78160.94540.49980.068*
C330.0264 (3)1.1380 (3)0.8515 (3)0.0837 (10)
H330.11801.14260.85640.100*
C620.8015 (3)0.8267 (3)0.8485 (2)0.0601 (7)
H620.79710.89700.86430.072*
C270.4732 (4)0.3993 (3)0.7156 (3)0.0979 (12)
H27A0.39200.36850.72250.147*
H27B0.52200.34020.76800.147*
H27C0.52960.41740.63570.147*
C671.0581 (3)0.5573 (3)0.8253 (3)0.0866 (10)
H67A1.13440.60170.80460.130*
H67B1.07130.51890.76810.130*
H67C1.05050.49740.90210.130*
C350.1509 (4)1.2042 (3)0.8827 (3)0.0787 (9)
H350.18071.25510.90790.094*
C540.8809 (3)1.1902 (3)0.4807 (3)0.0815 (10)
H540.94801.24250.43570.098*
C530.8802 (3)1.0910 (3)0.4533 (3)0.0744 (9)
H530.94751.07560.38990.089*
C340.0168 (4)1.2130 (3)0.8879 (3)0.0824 (10)
H340.04471.27010.91610.099*
C550.7824 (4)1.2126 (3)0.5746 (3)0.0879 (10)
H550.78341.27930.59450.106*
N20.4019 (3)0.8323 (2)1.00562 (19)0.0616 (6)
N10.4387 (2)0.84879 (17)0.89004 (16)0.0450 (5)
O10.41972 (19)1.10153 (17)0.57916 (16)0.0691 (6)
O20.4901 (2)0.85139 (19)1.04107 (17)0.0755 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0387 (14)0.0510 (15)0.0411 (13)0.0047 (12)0.0056 (12)0.0083 (12)
C610.0424 (15)0.0484 (15)0.0371 (13)0.0020 (12)0.0100 (11)0.0072 (11)
C60.0449 (15)0.0452 (14)0.0415 (14)0.0028 (12)0.0103 (12)0.0103 (11)
C30.0399 (14)0.0465 (14)0.0435 (14)0.0011 (11)0.0127 (12)0.0114 (11)
C210.0387 (14)0.0486 (15)0.0455 (15)0.0015 (12)0.0105 (12)0.0080 (12)
C660.0457 (17)0.0588 (18)0.0752 (19)0.0012 (14)0.0188 (15)0.0224 (15)
C510.0453 (16)0.0479 (15)0.0440 (14)0.0013 (12)0.0092 (12)0.0061 (12)
C50.0431 (15)0.0431 (14)0.0399 (13)0.0008 (11)0.0056 (11)0.0120 (11)
C240.0610 (19)0.0468 (16)0.075 (2)0.0015 (13)0.0198 (16)0.0177 (15)
C310.0440 (16)0.0454 (14)0.0446 (14)0.0039 (12)0.0080 (12)0.0105 (12)
C320.0501 (19)0.0681 (19)0.077 (2)0.0020 (15)0.0108 (15)0.0268 (16)
C230.068 (2)0.0425 (16)0.071 (2)0.0107 (14)0.0210 (16)0.0006 (14)
C650.0582 (19)0.0508 (16)0.077 (2)0.0027 (14)0.0202 (16)0.0177 (15)
C640.0435 (16)0.0621 (18)0.0502 (16)0.0035 (14)0.0142 (13)0.0048 (13)
C250.0578 (18)0.0618 (18)0.0600 (17)0.0024 (14)0.0154 (14)0.0237 (15)
C220.0551 (17)0.0528 (17)0.0516 (16)0.0049 (13)0.0150 (13)0.0053 (13)
C560.068 (2)0.0542 (18)0.079 (2)0.0130 (16)0.0000 (17)0.0185 (16)
C360.0562 (18)0.0692 (19)0.0662 (18)0.0017 (15)0.0119 (15)0.0272 (16)
C40.0496 (16)0.0454 (15)0.0394 (14)0.0009 (12)0.0088 (12)0.0066 (12)
C630.0495 (18)0.079 (2)0.075 (2)0.0025 (16)0.0281 (15)0.0212 (17)
C260.0491 (16)0.0425 (15)0.0509 (16)0.0034 (12)0.0140 (13)0.0077 (12)
C520.0440 (16)0.0737 (19)0.0452 (15)0.0024 (14)0.0127 (13)0.0125 (14)
C330.0494 (19)0.088 (2)0.096 (3)0.0138 (18)0.0053 (18)0.034 (2)
C620.0556 (19)0.0634 (18)0.0646 (18)0.0008 (15)0.0221 (15)0.0225 (15)
C270.121 (3)0.058 (2)0.116 (3)0.004 (2)0.030 (3)0.034 (2)
C670.054 (2)0.087 (2)0.101 (2)0.0120 (17)0.0250 (18)0.018 (2)
C350.088 (3)0.075 (2)0.072 (2)0.0036 (19)0.0092 (19)0.0392 (18)
C540.062 (2)0.086 (3)0.074 (2)0.0299 (19)0.0129 (18)0.0056 (19)
C530.0451 (18)0.105 (3)0.0545 (18)0.0148 (18)0.0066 (15)0.0082 (18)
C340.079 (3)0.066 (2)0.076 (2)0.0119 (19)0.0081 (19)0.0302 (18)
C550.087 (3)0.062 (2)0.103 (3)0.0272 (19)0.015 (2)0.0135 (19)
N20.0650 (16)0.0742 (16)0.0396 (13)0.0009 (12)0.0139 (12)0.0168 (11)
N10.0431 (13)0.0513 (12)0.0335 (11)0.0010 (10)0.0079 (9)0.0102 (9)
O10.0572 (13)0.0674 (13)0.0526 (11)0.0023 (10)0.0130 (9)0.0071 (10)
O20.0842 (16)0.0939 (16)0.0492 (11)0.0079 (12)0.0223 (11)0.0216 (11)
Geometric parameters (Å, º) top
C2—N11.469 (3)C64—C671.509 (4)
C2—C211.516 (3)C25—C261.375 (4)
C2—C31.546 (3)C25—H250.9300
C2—H20.9800C22—H220.9300
C61—C661.384 (3)C56—C551.383 (4)
C61—C621.387 (4)C56—H560.9300
C61—C61.513 (3)C36—C351.372 (4)
C6—N11.474 (3)C36—H360.9300
C6—C51.545 (3)C4—O11.210 (3)
C6—H60.9800C63—C621.380 (4)
C3—C311.512 (3)C63—H630.9300
C3—C41.514 (3)C26—H260.9300
C3—H30.9800C52—C531.382 (4)
C21—C261.381 (3)C52—H520.9300
C21—C221.387 (3)C33—C341.360 (5)
C66—C651.383 (4)C33—H330.9300
C66—H660.9300C62—H620.9300
C51—C521.382 (4)C27—H27A0.9600
C51—C561.383 (4)C27—H27B0.9600
C51—C51.507 (3)C27—H27C0.9600
C5—C41.526 (3)C67—H67A0.9600
C5—H50.9800C67—H67B0.9600
C24—C251.377 (4)C67—H67C0.9600
C24—C231.389 (4)C35—C341.363 (5)
C24—C271.514 (4)C35—H350.9300
C31—C321.375 (4)C54—C531.366 (4)
C31—C361.380 (4)C54—C551.371 (5)
C32—C331.390 (4)C54—H540.9300
C32—H320.9300C53—H530.9300
C23—C221.371 (4)C34—H340.9300
C23—H230.9300C55—H550.9300
C65—C641.380 (4)N2—O21.239 (3)
C65—H650.9300N2—N11.335 (3)
C64—C631.371 (4)
N1—C2—C21111.43 (19)C23—C22—H22119.3
N1—C2—C3108.96 (19)C21—C22—H22119.3
C21—C2—C3116.0 (2)C55—C56—C51121.3 (3)
N1—C2—H2106.6C55—C56—H56119.3
C21—C2—H2106.6C51—C56—H56119.3
C3—C2—H2106.6C35—C36—C31121.3 (3)
C66—C61—C62116.9 (2)C35—C36—H36119.4
C66—C61—C6122.4 (2)C31—C36—H36119.4
C62—C61—C6120.5 (2)O1—C4—C3120.0 (2)
N1—C6—C61113.52 (19)O1—C4—C5121.1 (2)
N1—C6—C5111.25 (19)C3—C4—C5118.7 (2)
C61—C6—C5110.10 (19)C64—C63—C62121.9 (3)
N1—C6—H6107.2C64—C63—H63119.1
C61—C6—H6107.2C62—C63—H63119.1
C5—C6—H6107.2C25—C26—C21120.8 (2)
C31—C3—C4111.2 (2)C25—C26—H26119.6
C31—C3—C2113.5 (2)C21—C26—H26119.6
C4—C3—C2113.51 (19)C51—C52—C53120.5 (3)
C31—C3—H3106.0C51—C52—H52119.8
C4—C3—H3106.0C53—C52—H52119.8
C2—C3—H3106.0C34—C33—C32120.1 (3)
C26—C21—C22117.6 (2)C34—C33—H33119.9
C26—C21—C2123.9 (2)C32—C33—H33119.9
C22—C21—C2118.5 (2)C63—C62—C61121.2 (3)
C65—C66—C61121.2 (3)C63—C62—H62119.4
C65—C66—H66119.4C61—C62—H62119.4
C61—C66—H66119.4C24—C27—H27A109.5
C52—C51—C56118.1 (3)C24—C27—H27B109.5
C52—C51—C5121.0 (2)H27A—C27—H27B109.5
C56—C51—C5120.8 (2)C24—C27—H27C109.5
C51—C5—C4112.48 (19)H27A—C27—H27C109.5
C51—C5—C6110.7 (2)H27B—C27—H27C109.5
C4—C5—C6114.74 (19)C64—C67—H67A109.5
C51—C5—H5106.1C64—C67—H67B109.5
C4—C5—H5106.1H67A—C67—H67B109.5
C6—C5—H5106.1C64—C67—H67C109.5
C25—C24—C23117.2 (3)H67A—C67—H67C109.5
C25—C24—C27121.1 (3)H67B—C67—H67C109.5
C23—C24—C27121.7 (3)C34—C35—C36120.5 (3)
C32—C31—C36117.6 (3)C34—C35—H35119.8
C32—C31—C3120.3 (2)C36—C35—H35119.8
C36—C31—C3122.1 (2)C53—C54—C55119.8 (3)
C31—C32—C33120.9 (3)C53—C54—H54120.1
C31—C32—H32119.5C55—C54—H54120.1
C33—C32—H32119.5C54—C53—C52120.6 (3)
C22—C23—C24121.2 (3)C54—C53—H53119.7
C22—C23—H23119.4C52—C53—H53119.7
C24—C23—H23119.4C33—C34—C35119.6 (3)
C64—C65—C66121.6 (3)C33—C34—H34120.2
C64—C65—H65119.2C35—C34—H34120.2
C66—C65—H65119.2C54—C55—C56119.6 (3)
C63—C64—C65117.1 (3)C54—C55—H55120.2
C63—C64—C67121.6 (3)C56—C55—H55120.2
C65—C64—C67121.2 (3)O2—N2—N1114.2 (2)
C26—C25—C24121.9 (3)N2—N1—C2115.1 (2)
C26—C25—H25119.1N2—N1—C6120.7 (2)
C24—C25—H25119.1C2—N1—C6123.50 (18)
C23—C22—C21121.3 (3)
C66—C61—C6—N158.6 (3)C5—C51—C56—C55179.0 (3)
C62—C61—C6—N1127.2 (2)C32—C31—C36—C351.0 (4)
C66—C61—C6—C566.9 (3)C3—C31—C36—C35177.4 (3)
C62—C61—C6—C5107.3 (3)C31—C3—C4—O157.5 (3)
N1—C2—C3—C3184.1 (2)C2—C3—C4—O1173.2 (2)
C21—C2—C3—C31149.3 (2)C31—C3—C4—C5126.0 (2)
N1—C2—C3—C444.1 (3)C2—C3—C4—C53.4 (3)
C21—C2—C3—C482.5 (3)C51—C5—C4—O118.8 (3)
N1—C2—C21—C26112.3 (3)C6—C5—C4—O1146.5 (2)
C3—C2—C21—C2613.1 (3)C51—C5—C4—C3164.7 (2)
N1—C2—C21—C2266.7 (3)C6—C5—C4—C337.0 (3)
C3—C2—C21—C22167.9 (2)C65—C64—C63—C620.3 (4)
C62—C61—C66—C650.9 (4)C67—C64—C63—C62178.8 (3)
C6—C61—C66—C65175.2 (2)C24—C25—C26—C210.5 (4)
C52—C51—C5—C4111.5 (3)C22—C21—C26—C251.2 (4)
C56—C51—C5—C468.0 (3)C2—C21—C26—C25177.8 (2)
C52—C51—C5—C6118.7 (2)C56—C51—C52—C531.1 (4)
C56—C51—C5—C661.8 (3)C5—C51—C52—C53178.3 (2)
N1—C6—C5—C51161.4 (2)C31—C32—C33—C341.1 (5)
C61—C6—C5—C5171.9 (3)C64—C63—C62—C610.5 (4)
N1—C6—C5—C432.8 (3)C66—C61—C62—C630.3 (4)
C61—C6—C5—C4159.5 (2)C6—C61—C62—C63174.2 (2)
C4—C3—C31—C32133.9 (3)C31—C36—C35—C340.9 (5)
C2—C3—C31—C3296.7 (3)C55—C54—C53—C520.5 (5)
C4—C3—C31—C3644.6 (3)C51—C52—C53—C540.7 (4)
C2—C3—C31—C3684.8 (3)C32—C33—C34—C351.3 (5)
C36—C31—C32—C330.1 (4)C36—C35—C34—C330.3 (5)
C3—C31—C32—C33178.4 (3)C53—C54—C55—C561.2 (5)
C25—C24—C23—C220.8 (4)C51—C56—C55—C540.7 (5)
C27—C24—C23—C22179.9 (3)O2—N2—N1—C2175.7 (2)
C61—C66—C65—C641.8 (4)O2—N2—N1—C65.0 (3)
C66—C65—C64—C631.5 (4)C21—C2—N1—N2111.8 (2)
C66—C65—C64—C67177.7 (3)C3—C2—N1—N2119.0 (2)
C23—C24—C25—C260.6 (4)C21—C2—N1—C677.9 (3)
C27—C24—C25—C26179.9 (3)C3—C2—N1—C651.4 (3)
C24—C23—C22—C210.0 (4)C61—C6—N1—N277.1 (3)
C26—C21—C22—C231.0 (4)C5—C6—N1—N2158.0 (2)
C2—C21—C22—C23178.1 (2)C61—C6—N1—C2113.0 (2)
C52—C51—C56—C550.4 (4)C5—C6—N1—C211.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C66—H66···Cg0.932.693.613 (4)169
C67—H67A···Cgi0.962.723.608 (4)153
Symmetry code: (i) x+1, y, z.
 

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