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The piperidone ring of the title compound, C31H28N2O4, adopts a twist boat conformation. The crystal packing is characterized by a layered arrangement of mol­ecules held together by C—H...O hydrogen bonds, in which each of the nitro­so and carbonyl O atoms participate. No significant aryl–aryl interactions are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000954/gh6010sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000954/gh6010Isup2.hkl
Contains datablock I

CCDC reference: 263707

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.051
  • wR factor = 0.151
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.26 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33 PLAT480_ALERT_4_C Long H...A H-Bond Reported H26 .. O2 .. 2.62 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H67A .. O2 .. 2.62 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97.

2,6-Bis(4-methoxyphenyl)-1-nitroso-3,5-diphenylpiperidin-4-one top
Crystal data top
C31H28N2O4F(000) = 1040
Mr = 492.55Dx = 1.261 Mg m3
Monoclinic, P21/nMelting point: 476 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.8364 (8) ÅCell parameters from 5412 reflections
b = 19.4649 (15) Åθ = 2.2–27.2°
c = 12.6722 (10) ŵ = 0.08 mm1
β = 103.926 (1)°T = 293 K
V = 2594.4 (3) Å3Plates, yellow
Z = 40.28 × 0.22 × 0.16 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5783 independent reflections
Radiation source: fine-focus sealed tube4264 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ or ω scans?θmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1213
Tmin = 0.90, Tmax = 0.99k = 2525
15676 measured reflectionsl = 1615
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0796P)2 + 0.332P]
where P = (Fo2 + 2Fc2)/3
5783 reflections(Δ/σ)max < 0.001
334 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.14 e Å3
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
O10.83279 (13)0.22517 (6)0.28065 (11)0.0667 (3)
O20.52329 (11)0.06836 (6)0.04872 (8)0.0547 (3)
O30.57672 (16)0.08778 (8)0.64153 (10)0.0806 (4)
O40.92407 (15)0.17451 (7)0.39526 (12)0.0829 (5)
N10.79216 (12)0.12497 (6)0.20969 (10)0.0440 (3)
N20.87313 (14)0.17673 (7)0.23730 (12)0.0570 (4)
C20.83396 (14)0.07025 (8)0.14615 (13)0.0474 (4)
H20.91710.08450.13610.057*
C40.60405 (14)0.07243 (7)0.03482 (12)0.0419 (3)
C210.85563 (14)0.00329 (8)0.20911 (13)0.0482 (4)
C220.95121 (16)0.00203 (9)0.30429 (15)0.0572 (4)
H220.99910.04150.32550.069*
C230.97732 (17)0.05562 (9)0.36820 (16)0.0632 (5)
H231.04240.05510.43120.076*
C240.90627 (18)0.11442 (8)0.33829 (15)0.0609 (5)
C250.81103 (17)0.11466 (9)0.24307 (15)0.0608 (5)
H250.76310.15420.22220.073*
C260.78727 (15)0.05666 (8)0.17936 (14)0.0540 (4)
H260.72410.05770.11510.065*
C271.0187 (3)0.17499 (11)0.4942 (2)0.1017 (9)
H27A1.02220.21970.52690.153*
H27B0.99820.14130.54270.153*
H27C1.09970.16430.48010.153*
C30.74351 (15)0.06921 (8)0.03230 (12)0.0474 (4)
H30.75700.02570.00220.057*
C310.77261 (16)0.12679 (10)0.03854 (13)0.0563 (4)
C320.8381 (2)0.11420 (14)0.11674 (18)0.0871 (7)
H320.86570.06990.12660.104*
C330.8634 (3)0.1682 (2)0.1819 (2)0.1145 (10)
H330.90840.15940.23430.137*
C340.8235 (3)0.23261 (19)0.1696 (2)0.1108 (10)
H340.83920.26770.21450.133*
C350.7605 (3)0.24627 (14)0.0919 (2)0.0977 (8)
H350.73420.29080.08230.117*
C360.7353 (2)0.19380 (10)0.02676 (16)0.0736 (6)
H360.69210.20380.02650.088*
C50.57287 (13)0.07906 (7)0.14524 (11)0.0394 (3)
H50.58740.03370.17970.047*
C510.43551 (14)0.09710 (8)0.13803 (12)0.0447 (3)
C520.37838 (18)0.15127 (9)0.07422 (16)0.0626 (5)
H520.42490.17610.03440.075*
C530.2545 (2)0.16934 (12)0.0683 (2)0.0867 (7)
H530.21740.20540.02360.104*
C540.1864 (2)0.13464 (14)0.1275 (3)0.0998 (9)
H540.10310.14750.12500.120*
C550.2403 (2)0.08061 (14)0.1911 (2)0.0924 (8)
H550.19280.05660.23110.111*
C560.36544 (18)0.06110 (10)0.19675 (16)0.0643 (5)
H560.40130.02410.23980.077*
C60.66115 (14)0.12995 (7)0.22228 (11)0.0407 (3)
H60.63090.17640.19970.049*
C610.65001 (14)0.12069 (7)0.33847 (11)0.0435 (3)
C620.60150 (17)0.17300 (8)0.38929 (13)0.0522 (4)
H620.58530.21540.35480.063*
C630.57602 (18)0.16434 (9)0.49069 (14)0.0601 (4)
H630.54240.20040.52290.072*
C640.60062 (17)0.10248 (9)0.54308 (13)0.0580 (4)
C650.65232 (18)0.04954 (9)0.49450 (14)0.0616 (5)
H650.67100.00780.53040.074*
C660.67624 (17)0.05846 (8)0.39337 (13)0.0541 (4)
H660.71030.02240.36140.065*
C670.5134 (3)0.13859 (15)0.68988 (17)0.0965 (8)
H67A0.50240.12200.75840.145*
H67B0.43170.14820.64260.145*
H67C0.56340.17990.70130.145*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0698 (9)0.0490 (6)0.0772 (8)0.0097 (6)0.0099 (7)0.0091 (6)
O20.0474 (7)0.0762 (7)0.0393 (6)0.0072 (5)0.0082 (5)0.0001 (5)
O30.1022 (11)0.0979 (10)0.0468 (7)0.0094 (8)0.0277 (7)0.0060 (7)
O40.0913 (11)0.0573 (7)0.0814 (9)0.0072 (7)0.0156 (8)0.0004 (6)
N10.0392 (7)0.0459 (6)0.0460 (6)0.0066 (5)0.0083 (5)0.0048 (5)
N20.0550 (9)0.0493 (7)0.0633 (9)0.0114 (6)0.0078 (7)0.0045 (6)
C20.0339 (8)0.0555 (8)0.0544 (9)0.0036 (6)0.0137 (7)0.0086 (7)
C40.0420 (9)0.0422 (7)0.0423 (7)0.0048 (6)0.0117 (6)0.0007 (6)
C210.0328 (8)0.0539 (8)0.0560 (9)0.0033 (6)0.0074 (7)0.0102 (7)
C220.0428 (9)0.0547 (9)0.0675 (11)0.0012 (7)0.0005 (8)0.0138 (8)
C230.0519 (11)0.0618 (10)0.0644 (11)0.0087 (8)0.0088 (8)0.0124 (8)
C240.0572 (11)0.0499 (9)0.0682 (11)0.0108 (8)0.0009 (9)0.0077 (8)
C250.0502 (10)0.0506 (9)0.0737 (11)0.0010 (7)0.0005 (8)0.0125 (8)
C260.0409 (9)0.0541 (9)0.0602 (10)0.0030 (7)0.0011 (7)0.0092 (7)
C270.134 (2)0.0658 (12)0.0782 (14)0.0184 (13)0.0275 (14)0.0036 (11)
C30.0420 (9)0.0547 (8)0.0480 (8)0.0015 (7)0.0159 (7)0.0093 (6)
C310.0471 (10)0.0783 (11)0.0467 (8)0.0154 (8)0.0178 (7)0.0060 (8)
C320.0778 (15)0.1218 (18)0.0761 (13)0.0131 (13)0.0468 (12)0.0116 (13)
C330.096 (2)0.185 (3)0.0828 (16)0.024 (2)0.0605 (16)0.0108 (19)
C340.100 (2)0.149 (3)0.0865 (18)0.044 (2)0.0286 (16)0.0330 (18)
C350.112 (2)0.0946 (16)0.0895 (17)0.0263 (14)0.0300 (15)0.0220 (13)
C360.0882 (15)0.0740 (12)0.0662 (11)0.0101 (11)0.0334 (11)0.0082 (10)
C50.0374 (8)0.0423 (7)0.0390 (7)0.0022 (6)0.0098 (6)0.0005 (5)
C510.0404 (8)0.0486 (8)0.0459 (8)0.0046 (6)0.0120 (6)0.0089 (6)
C520.0520 (11)0.0606 (10)0.0764 (12)0.0077 (8)0.0176 (9)0.0017 (9)
C530.0573 (14)0.0830 (14)0.1145 (18)0.0213 (11)0.0103 (13)0.0091 (13)
C540.0490 (13)0.0965 (18)0.158 (3)0.0023 (12)0.0333 (15)0.0350 (18)
C550.0659 (15)0.0979 (17)0.131 (2)0.0248 (13)0.0586 (15)0.0273 (15)
C560.0588 (12)0.0678 (11)0.0751 (12)0.0121 (8)0.0333 (10)0.0072 (9)
C60.0395 (8)0.0419 (7)0.0408 (7)0.0019 (6)0.0100 (6)0.0009 (6)
C610.0418 (8)0.0485 (8)0.0389 (7)0.0060 (6)0.0072 (6)0.0038 (6)
C620.0625 (11)0.0479 (8)0.0480 (8)0.0034 (7)0.0167 (8)0.0030 (6)
C630.0708 (12)0.0626 (10)0.0518 (9)0.0051 (8)0.0241 (9)0.0114 (8)
C640.0607 (11)0.0734 (11)0.0399 (8)0.0131 (9)0.0122 (7)0.0017 (8)
C650.0711 (12)0.0634 (10)0.0479 (9)0.0008 (9)0.0095 (8)0.0116 (8)
C660.0598 (11)0.0534 (9)0.0485 (9)0.0049 (7)0.0118 (7)0.0006 (7)
C670.1097 (19)0.138 (2)0.0538 (11)0.0003 (16)0.0425 (13)0.0025 (13)
Geometric parameters (Å, º) top
O1—N21.2237 (18)C34—C351.353 (4)
O2—C41.2029 (18)C34—H340.9300
O3—C641.364 (2)C35—C361.381 (3)
O3—C671.424 (3)C35—H350.9300
O4—C241.363 (2)C36—H360.9300
O4—C271.416 (3)C5—C511.511 (2)
N1—N21.3265 (17)C5—C61.5492 (19)
N1—C61.4695 (19)C5—H50.9800
N1—C21.4709 (18)C51—C561.376 (2)
C2—C211.517 (2)C51—C521.381 (2)
C2—C31.537 (2)C52—C531.372 (3)
C2—H20.9800C52—H520.9300
C4—C31.521 (2)C53—C541.353 (4)
C4—C51.5219 (19)C53—H530.9300
C21—C261.385 (2)C54—C551.367 (4)
C21—C221.388 (2)C54—H540.9300
C22—C231.373 (3)C55—C561.394 (3)
C22—H220.9300C55—H550.9300
C23—C241.381 (2)C56—H560.9300
C23—H230.9300C6—C611.5167 (19)
C24—C251.386 (2)C6—H60.9800
C25—C261.376 (2)C61—C621.375 (2)
C25—H250.9300C61—C661.392 (2)
C26—H260.9300C62—C631.388 (2)
C27—H27A0.9600C62—H620.9300
C27—H27B0.9600C63—C641.370 (3)
C27—H27C0.9600C63—H630.9300
C3—C311.516 (2)C64—C651.386 (3)
C3—H30.9800C65—C661.378 (2)
C31—C321.373 (2)C65—H650.9300
C31—C361.384 (3)C66—H660.9300
C32—C331.404 (4)C67—H67A0.9600
C32—H320.9300C67—H67B0.9600
C33—C341.348 (4)C67—H67C0.9600
C33—H330.9300
C64—O3—C67117.71 (16)C36—C35—H35120.1
C24—O4—C27117.04 (16)C35—C36—C31121.9 (2)
N2—N1—C6121.08 (12)C35—C36—H36119.1
N2—N1—C2115.03 (12)C31—C36—H36119.1
C6—N1—C2122.68 (11)C51—C5—C4113.44 (12)
O1—N2—N1114.74 (14)C51—C5—C6109.85 (11)
N1—C2—C21111.31 (12)C4—C5—C6113.17 (11)
N1—C2—C3108.22 (12)C51—C5—H5106.6
C21—C2—C3117.75 (13)C4—C5—H5106.6
N1—C2—H2106.3C6—C5—H5106.6
C21—C2—H2106.3C56—C51—C52118.52 (16)
C3—C2—H2106.3C56—C51—C5120.85 (15)
O2—C4—C3119.67 (13)C52—C51—C5120.61 (14)
O2—C4—C5122.63 (13)C53—C52—C51121.49 (19)
C3—C4—C5117.68 (13)C53—C52—H52119.3
C26—C21—C22117.38 (15)C51—C52—H52119.3
C26—C21—C2125.16 (14)C54—C53—C52119.9 (2)
C22—C21—C2117.45 (14)C54—C53—H53120.0
C23—C22—C21122.12 (16)C52—C53—H53120.0
C23—C22—H22118.9C53—C54—C55119.9 (2)
C21—C22—H22118.9C53—C54—H54120.1
C22—C23—C24119.58 (16)C55—C54—H54120.1
C22—C23—H23120.2C54—C55—C56120.8 (2)
C24—C23—H23120.2C54—C55—H55119.6
O4—C24—C23124.56 (16)C56—C55—H55119.6
O4—C24—C25116.03 (16)C51—C56—C55119.4 (2)
C23—C24—C25119.40 (17)C51—C56—H56120.3
C26—C25—C24120.20 (16)C55—C56—H56120.3
C26—C25—H25119.9N1—C6—C61113.72 (12)
C24—C25—H25119.9N1—C6—C5110.83 (11)
C25—C26—C21121.29 (16)C61—C6—C5110.76 (11)
C25—C26—H26119.4N1—C6—H6107.1
C21—C26—H26119.4C61—C6—H6107.1
O4—C27—H27A109.5C5—C6—H6107.1
O4—C27—H27B109.5C62—C61—C66117.74 (14)
H27A—C27—H27B109.5C62—C61—C6119.69 (13)
O4—C27—H27C109.5C66—C61—C6122.30 (13)
H27A—C27—H27C109.5C61—C62—C63121.82 (15)
H27B—C27—H27C109.5C61—C62—H62119.1
C31—C3—C4109.35 (13)C63—C62—H62119.1
C31—C3—C2111.69 (13)C64—C63—C62119.77 (16)
C4—C3—C2113.10 (12)C64—C63—H63120.1
C31—C3—H3107.5C62—C63—H63120.1
C4—C3—H3107.5O3—C64—C63124.76 (17)
C2—C3—H3107.5O3—C64—C65115.86 (16)
C32—C31—C36117.46 (18)C63—C64—C65119.38 (15)
C32—C31—C3120.86 (18)C66—C65—C64120.40 (16)
C36—C31—C3121.68 (14)C66—C65—H65119.8
C31—C32—C33119.9 (2)C64—C65—H65119.8
C31—C32—H32120.0C65—C66—C61120.86 (15)
C33—C32—H32120.0C65—C66—H66119.6
C34—C33—C32121.0 (2)C61—C66—H66119.6
C34—C33—H33119.5O3—C67—H67A109.5
C32—C33—H33119.5O3—C67—H67B109.5
C33—C34—C35120.0 (2)H67A—C67—H67B109.5
C33—C34—H34120.0O3—C67—H67C109.5
C35—C34—H34120.0H67A—C67—H67C109.5
C34—C35—C36119.8 (3)H67B—C67—H67C109.5
C34—C35—H35120.1
C6—N1—N2—O15.3 (2)C3—C31—C36—C35179.3 (2)
C2—N1—N2—O1173.10 (13)O2—C4—C5—C5113.9 (2)
N2—N1—C2—C21114.60 (14)C3—C4—C5—C51167.57 (12)
C6—N1—C2—C2177.84 (16)O2—C4—C5—C6139.95 (14)
N2—N1—C2—C3114.52 (14)C3—C4—C5—C641.55 (17)
C6—N1—C2—C353.04 (17)C4—C5—C51—C56131.65 (15)
N1—C2—C21—C26116.08 (16)C6—C5—C51—C56100.58 (16)
C3—C2—C21—C269.7 (2)C4—C5—C51—C5249.91 (19)
N1—C2—C21—C2263.66 (18)C6—C5—C51—C5277.86 (17)
C3—C2—C21—C22170.58 (14)C56—C51—C52—C530.2 (3)
C26—C21—C22—C230.8 (2)C5—C51—C52—C53178.68 (18)
C2—C21—C22—C23178.97 (16)C51—C52—C53—C541.4 (3)
C21—C22—C23—C240.6 (3)C52—C53—C54—C551.6 (4)
C27—O4—C24—C232.9 (3)C53—C54—C55—C560.7 (4)
C27—O4—C24—C25178.4 (2)C52—C51—C56—C550.7 (3)
C22—C23—C24—O4179.78 (18)C5—C51—C56—C55177.80 (17)
C22—C23—C24—C251.1 (3)C54—C55—C56—C510.4 (3)
O4—C24—C25—C26179.10 (17)N2—N1—C6—C6177.39 (16)
C23—C24—C25—C260.3 (3)C2—N1—C6—C61115.78 (14)
C24—C25—C26—C211.1 (3)N2—N1—C6—C5157.07 (13)
C22—C21—C26—C251.6 (2)C2—N1—C6—C59.76 (17)
C2—C21—C26—C25178.15 (15)C51—C5—C6—N1165.66 (11)
O2—C4—C3—C3158.73 (18)C4—C5—C6—N137.75 (16)
C5—C4—C3—C31122.73 (14)C51—C5—C6—C6167.15 (15)
O2—C4—C3—C2176.13 (13)C4—C5—C6—C61164.93 (12)
C5—C4—C3—C22.42 (18)N1—C6—C61—C62119.26 (15)
N1—C2—C3—C3177.48 (15)C5—C6—C61—C62115.16 (15)
C21—C2—C3—C31155.26 (13)N1—C6—C61—C6666.83 (18)
N1—C2—C3—C446.40 (16)C5—C6—C61—C6658.75 (19)
C21—C2—C3—C480.86 (16)C66—C61—C62—C631.6 (2)
C4—C3—C31—C32131.97 (18)C6—C61—C62—C63172.60 (15)
C2—C3—C31—C32102.07 (19)C61—C62—C63—C640.7 (3)
C4—C3—C31—C3648.4 (2)C67—O3—C64—C634.7 (3)
C2—C3—C31—C3677.5 (2)C67—O3—C64—C65174.61 (19)
C36—C31—C32—C330.8 (3)C62—C63—C64—O3178.45 (17)
C3—C31—C32—C33179.6 (2)C62—C63—C64—C650.8 (3)
C31—C32—C33—C340.5 (4)O3—C64—C65—C66177.93 (17)
C32—C33—C34—C351.5 (5)C63—C64—C65—C661.4 (3)
C33—C34—C35—C361.2 (4)C64—C65—C66—C610.5 (3)
C34—C35—C36—C310.1 (4)C62—C61—C66—C651.0 (2)
C32—C31—C36—C351.1 (3)C6—C61—C66—C65173.03 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C25—H25···O1i0.932.573.467 (2)163
C26—H26···O2ii0.932.623.382 (2)140
C27—H27A···O1iii0.962.573.078 (3)114
C67—H67A···O2iv0.962.623.562 (2)168
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+2, y, z+1; (iv) x, y, z+1.
 

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