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The piperidine ring of the title compound, C25H23NO2, is in a distorted boat form. The phenyl ring at position 2 makes a dihedral angle of 80.6 (1)° with the phenyl ring of the benzyl group at position 3, and 61.2 (1)° with the phenyl ring at position 6. The dihedral angle between the phenyl ring of the benzyl group and the phenyl ring at position 6 is 84.2 (1)°. The formyl group and the phenyl ring at position 6 have equatorial orientations. The phenyl ring at position 2 and the benzyl group at position 3 have axial orientations. C—H...O and C—H...π hydrogen bonds are found in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053846/hg2335sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053846/hg2335Isup2.hkl
Contains datablock I

CCDC reference: 672809

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.048
  • wR factor = 0.142
  • Data-to-parameter ratio = 27.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.30 PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C1 .. 5.66 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C23 - C24 .. 6.27 su
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.978 Tmax scaled 0.978 Tmin scaled 0.948 PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C6 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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

Comment top

Jayabharathi et al. (2007) have reported synthesis, stereochemistry and antimicrobial evaluation of t3-benzyl-r2,c6-diarylpiperidin- 4-one and its derivatives. Balamurugan et al. (2007) have reported a crystal structure of t3,t5-Dimethyl-r2,c-6-diphenylpiperidin-4-one wherein the piperidine ring is in chair form. The piperidine ring of the title molecule, C25H23NO2, is in distorted boat form. The phenyl ring at position 2 makes a dihedral angle of 80.6 (1)° with the phenyl ring of benzyl moiety at 3, and 61.2 (1)° with the phenyl ring at 6. The dihedral angle between the phenyl ring of the benzyl moiety and the phenyl ring at 6 is 84.2 (1)°. The formyl group at N, is nearly co-planar with the adjacent C2 and C6 atoms. The phenyl ring at 6 is in equatorial orientations. The phenyl ring at 2, the benzyl group at 3 have axial orientations. C—H···O and C—H···π intra- and inter- molecular hydrogen bonds are found in the crystal structure (see Fig. 2, and hydrogen bonding table).

Related literature top

For a related crystal structure, see: Balamurugan et al. (2007). For applications of piperidines, see: Jayabharathi et al. (2007).

Experimental top

Jayabharathi et al. (2007) have reported the synthesis of the title compound.

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.93–0.98 Å and Uiso = 1.2Ueq(C).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atomic numbering and 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. The molecular packing of the title compound, viewed down the b axis showing the C—H···O (dashed lines) hydrogen bonds.
t-3-Benzyl-1-formyl-r-2,c-6-diphenylpiperidin-4-one top
Crystal data top
C25H23NO2F(000) = 784
Mr = 369.44Dx = 1.208 Mg m3
Monoclinic, P21/cMelting point: 355.5 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.5355 (3) ÅCell parameters from 7426 reflections
b = 9.3464 (2) Åθ = 4.4–32.4°
c = 21.0493 (5) ŵ = 0.08 mm1
β = 101.520 (3)°T = 200 K
V = 2030.95 (9) Å3Prism, colourless
Z = 40.41 × 0.37 × 0.29 mm
Data collection top
Oxford Diffraction Gemini
diffractometer
6871 independent reflections
Radiation source: fine-focus sealed tube3596 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 10.5081 pixels mm-1θmax = 32.5°, θmin = 4.5°
phi and ω scansh = 1515
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 1414
Tmin = 0.969, Tmax = 1.000l = 2831
29482 measured reflections
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0708P)2]
where P = (Fo2 + 2Fc2)/3
6871 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C25H23NO2V = 2030.95 (9) Å3
Mr = 369.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.5355 (3) ŵ = 0.08 mm1
b = 9.3464 (2) ÅT = 200 K
c = 21.0493 (5) Å0.41 × 0.37 × 0.29 mm
β = 101.520 (3)°
Data collection top
Oxford Diffraction Gemini
diffractometer
6871 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
3596 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 1.000Rint = 0.041
29482 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.142H-atom parameters constrained
S = 1.00Δρmax = 0.47 e Å3
6871 reflectionsΔρmin = 0.21 e Å3
253 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O10.54289 (11)0.47782 (12)0.30209 (5)0.0663 (4)
O40.38017 (9)0.07286 (10)0.42653 (5)0.0494 (3)
N10.41809 (9)0.29206 (10)0.32395 (5)0.0291 (3)
C10.46406 (13)0.38370 (16)0.28479 (7)0.0476 (5)
C20.47899 (11)0.28447 (12)0.39350 (5)0.0272 (3)
C30.51165 (10)0.12848 (12)0.41163 (5)0.0280 (3)
C40.39016 (11)0.03862 (13)0.39836 (6)0.0315 (3)
C50.28084 (11)0.09412 (13)0.34687 (6)0.0322 (3)
C60.32664 (11)0.17928 (13)0.29375 (5)0.0288 (3)
C130.61104 (12)0.06259 (13)0.37492 (6)0.0356 (4)
C210.39739 (10)0.35930 (12)0.43612 (6)0.0290 (3)
C220.34968 (13)0.49578 (14)0.41958 (7)0.0408 (4)
C230.27833 (13)0.56808 (15)0.45821 (8)0.0493 (5)
C240.25355 (13)0.50590 (16)0.51372 (8)0.0494 (5)
C250.30142 (14)0.37287 (17)0.53101 (7)0.0504 (5)
C260.37350 (12)0.29960 (14)0.49291 (6)0.0391 (4)
C310.74256 (11)0.13162 (13)0.38979 (6)0.0348 (4)
C320.78627 (14)0.21533 (17)0.34426 (8)0.0521 (5)
C330.90858 (16)0.27711 (19)0.35832 (10)0.0648 (7)
C340.98829 (15)0.25635 (17)0.41737 (10)0.0599 (6)
C350.94666 (14)0.17417 (17)0.46316 (8)0.0538 (5)
C360.82463 (12)0.11224 (15)0.44955 (7)0.0417 (4)
C610.21206 (11)0.23797 (13)0.24538 (5)0.0306 (3)
C620.16524 (12)0.15946 (15)0.18996 (6)0.0417 (4)
C630.05711 (14)0.20545 (18)0.14556 (7)0.0539 (5)
C640.00269 (14)0.33176 (17)0.15558 (7)0.0522 (5)
C650.04473 (13)0.41193 (16)0.21036 (7)0.0477 (4)
C660.15077 (13)0.36482 (14)0.25539 (6)0.0411 (4)
H10.432690.374170.240450.0572*
H20.561310.336330.399000.0326*
H30.548300.124220.458200.0336*
H5A0.225600.154680.367160.0386*
H5B0.229160.013820.327210.0386*
H60.373960.113760.270500.0345*
H13A0.620610.038290.385620.0427*
H13B0.576900.069960.328700.0427*
H220.365730.539160.382220.0489*
H230.247010.659330.446460.0592*
H240.204690.554070.539170.0593*
H250.285670.330700.568700.0605*
H260.406150.209360.505670.0469*
H320.733200.230310.303880.0625*
H330.936550.333130.327280.0777*
H341.070210.297720.426410.0718*
H351.000380.159920.503430.0646*
H360.797300.056790.480960.0501*
H620.206530.075070.182340.0500*
H630.025150.150640.108990.0647*
H640.074590.363100.125700.0627*
H650.005170.498080.217010.0573*
H660.180990.418530.292520.0494*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0586 (7)0.0752 (8)0.0630 (7)0.0297 (6)0.0070 (6)0.0227 (6)
O40.0559 (6)0.0402 (5)0.0461 (5)0.0080 (4)0.0044 (5)0.0154 (4)
N10.0267 (5)0.0356 (5)0.0253 (5)0.0036 (4)0.0056 (4)0.0048 (4)
C10.0425 (8)0.0609 (9)0.0394 (7)0.0103 (7)0.0081 (6)0.0160 (7)
C20.0221 (5)0.0320 (6)0.0264 (6)0.0005 (4)0.0024 (4)0.0001 (5)
C30.0272 (6)0.0320 (6)0.0232 (5)0.0035 (5)0.0009 (4)0.0002 (5)
C40.0343 (6)0.0322 (6)0.0277 (6)0.0008 (5)0.0054 (5)0.0013 (5)
C50.0267 (6)0.0353 (6)0.0324 (6)0.0047 (5)0.0008 (5)0.0032 (5)
C60.0264 (6)0.0345 (6)0.0244 (5)0.0021 (5)0.0025 (4)0.0001 (5)
C130.0335 (6)0.0394 (7)0.0323 (6)0.0087 (5)0.0027 (5)0.0069 (5)
C210.0227 (5)0.0329 (6)0.0295 (6)0.0000 (5)0.0010 (4)0.0052 (5)
C220.0425 (7)0.0350 (7)0.0437 (8)0.0013 (6)0.0058 (6)0.0030 (6)
C230.0405 (8)0.0370 (7)0.0665 (10)0.0092 (6)0.0013 (7)0.0161 (7)
C240.0345 (7)0.0592 (9)0.0552 (9)0.0053 (6)0.0106 (7)0.0239 (8)
C250.0470 (8)0.0666 (10)0.0411 (8)0.0051 (7)0.0170 (6)0.0077 (7)
C260.0376 (7)0.0454 (8)0.0354 (7)0.0075 (6)0.0099 (5)0.0000 (6)
C310.0289 (6)0.0395 (7)0.0369 (7)0.0102 (5)0.0088 (5)0.0056 (6)
C320.0415 (8)0.0699 (10)0.0483 (8)0.0140 (7)0.0171 (7)0.0110 (8)
C330.0499 (9)0.0666 (11)0.0873 (14)0.0055 (8)0.0365 (10)0.0123 (9)
C340.0335 (8)0.0563 (9)0.0925 (14)0.0016 (7)0.0191 (8)0.0149 (9)
C350.0341 (8)0.0657 (10)0.0584 (10)0.0081 (7)0.0016 (7)0.0175 (8)
C360.0341 (7)0.0504 (8)0.0396 (7)0.0060 (6)0.0050 (5)0.0042 (6)
C610.0273 (6)0.0414 (7)0.0230 (5)0.0037 (5)0.0048 (4)0.0048 (5)
C620.0404 (7)0.0514 (8)0.0305 (7)0.0116 (6)0.0005 (5)0.0036 (6)
C630.0469 (8)0.0779 (11)0.0310 (7)0.0146 (8)0.0066 (6)0.0097 (7)
C640.0404 (8)0.0774 (10)0.0346 (7)0.0211 (7)0.0026 (6)0.0058 (7)
C650.0398 (7)0.0539 (8)0.0469 (8)0.0176 (6)0.0025 (6)0.0031 (7)
C660.0374 (7)0.0470 (8)0.0366 (7)0.0087 (6)0.0016 (5)0.0037 (6)
Geometric parameters (Å, º) top
O1—C11.2147 (18)C62—C631.390 (2)
O4—C41.2138 (16)C63—C641.374 (2)
N1—C11.3443 (18)C64—C651.382 (2)
N1—C21.4781 (15)C65—C661.3847 (19)
N1—C61.4829 (15)C1—H10.9300
C2—C31.5288 (16)C2—H20.9800
C2—C211.5301 (16)C3—H30.9800
C3—C41.5096 (16)C5—H5A0.9700
C3—C131.5479 (17)C5—H5B0.9700
C4—C51.5072 (17)C6—H60.9800
C5—C61.5271 (17)C13—H13A0.9700
C6—C611.5178 (16)C13—H13B0.9700
C13—C311.5037 (17)C22—H220.9300
C21—C221.3897 (17)C23—H230.9300
C21—C261.3870 (17)C24—H240.9300
C22—C231.388 (2)C25—H250.9300
C23—C241.376 (2)C26—H260.9300
C24—C251.364 (2)C32—H320.9300
C25—C261.390 (2)C33—H330.9300
C31—C321.385 (2)C34—H340.9300
C31—C361.3886 (19)C35—H350.9300
C32—C331.389 (2)C36—H360.9300
C33—C341.368 (3)C62—H620.9300
C34—C351.371 (2)C63—H630.9300
C35—C361.387 (2)C64—H640.9300
C61—C621.3830 (17)C65—H650.9300
C61—C661.3861 (18)C66—H660.9300
O1···C6i3.2576 (16)C66···H33iv2.9700
O4···C3ii3.4093 (15)H1···C612.6700
O1···H222.8100H1···C663.0500
O1···H6i2.2900H1···C13i2.9600
O1···H13Bi2.9200H1···H13Bi2.3300
O1···H62i2.7500H2···O12.4100
O1···H22.4100H2···C312.7400
O4···H13A2.8500H2···C323.0500
O4···H3ii2.4400H2···C24v2.8100
O4···H26ii2.7300H3···C262.6700
N1···H13B2.6600H3···C362.9600
N1···H222.7200H3···H262.1100
N1···H662.7200H3···O4ii2.4400
C1···C223.459 (2)H5A···C22.8800
C1···C663.239 (2)H5A···C212.8300
C3···O4ii3.4093 (15)H5A···C34iv3.0500
C4···C263.1751 (18)H5A···C663.0500
C5···C213.2029 (17)H5B···C64ix3.0100
C5···C263.5906 (18)H5B···C65ix2.9900
C6···C133.3229 (17)H5B···H64ix2.5000
C6···O1iii3.2576 (16)H5B···H65ix2.4600
C13···C63.3229 (17)H6···C33.0400
C21···C53.2029 (17)H6···C133.0200
C22···C13.459 (2)H6···H13B2.2800
C26···C43.1751 (18)H6···H622.3200
C26···C53.5906 (18)H6···O1iii2.2900
C66···C13.239 (2)H13A···O42.8500
C1···H222.8700H13B···N12.6600
C1···H663.0400H13B···C62.7900
C1···H13Bi2.9200H13B···H62.2800
C2···H5A2.8800H13B···H322.3600
C3···H63.0400H13B···O1iii2.9200
C3···H262.5700H13B···C1iii2.9200
C4···H262.7400H13B···H1iii2.3300
C6···H13B2.7900H22···O12.8100
C13···H1iii2.9600H22···N12.7200
C13···H63.0200H22···C12.8700
C21···H5A2.8300H24···C33v3.1000
C22···H662.9900H24···C34v2.9800
C24···H34iv3.0800H24···C35v2.9900
C24···H2v2.8100H25···C62x3.0700
C25···H34iv3.0200H26···C32.5700
C26···H32.6700H26···C42.7400
C31···H22.7400H26···H32.1100
C32···H23.0500H26···O4ii2.7300
C33···H62i3.0900H32···H13B2.3600
C33···H24v3.1000H33···C65vi3.0000
C34···H5Avi3.0500H33···C66vi2.9700
C34···H24v2.9800H34···C24vi3.0800
C35···H24v2.9900H34···C25vi3.0200
C36···H32.9600H62···H62.3200
C61···H12.6700H62···O1iii2.7500
C62···H25vii3.0700H62···C33iii3.0900
C64···H5Bviii3.0100H64···H5Bviii2.5000
C65···H33iv3.0000H65···H5Bviii2.4600
C65···H5Bviii2.9900H66···N12.7200
C66···H13.0500H66···C13.0400
C66···H5A3.0500H66···C222.9900
C1—N1—C2119.98 (10)C2—C3—H3108.00
C1—N1—C6118.22 (10)C4—C3—H3108.00
C2—N1—C6120.45 (9)C13—C3—H3108.00
O1—C1—N1125.88 (13)C4—C5—H5A109.00
N1—C2—C3108.94 (9)C4—C5—H5B109.00
N1—C2—C21112.04 (9)C6—C5—H5A109.00
C3—C2—C21114.48 (9)C6—C5—H5B109.00
C2—C3—C4110.13 (9)H5A—C5—H5B108.00
C2—C3—C13113.31 (9)N1—C6—H6108.00
C4—C3—C13108.63 (9)C5—C6—H6108.00
O4—C4—C3122.70 (11)C61—C6—H6108.00
O4—C4—C5121.22 (11)C3—C13—H13A109.00
C3—C4—C5116.07 (10)C3—C13—H13B109.00
C4—C5—C6113.46 (10)C31—C13—H13A109.00
N1—C6—C5109.26 (9)C31—C13—H13B109.00
N1—C6—C61113.10 (10)H13A—C13—H13B108.00
C5—C6—C61110.75 (10)C21—C22—H22120.00
C3—C13—C31114.36 (10)C23—C22—H22120.00
C2—C21—C22119.35 (11)C22—C23—H23120.00
C2—C21—C26122.78 (10)C24—C23—H23120.00
C22—C21—C26117.80 (11)C23—C24—H24120.00
C21—C22—C23120.74 (13)C25—C24—H24120.00
C22—C23—C24120.57 (13)C24—C25—H25120.00
C23—C24—C25119.28 (14)C26—C25—H25120.00
C24—C25—C26120.72 (14)C21—C26—H26120.00
C21—C26—C25120.87 (12)C25—C26—H26120.00
C13—C31—C32121.21 (12)C31—C32—H32120.00
C13—C31—C36120.92 (11)C33—C32—H32120.00
C32—C31—C36117.87 (12)C32—C33—H33120.00
C31—C32—C33120.65 (15)C34—C33—H33120.00
C32—C33—C34120.65 (17)C33—C34—H34120.00
C33—C34—C35119.58 (16)C35—C34—H34120.00
C34—C35—C36120.14 (15)C34—C35—H35120.00
C31—C36—C35121.10 (13)C36—C35—H35120.00
C6—C61—C62118.42 (11)C31—C36—H36119.00
C6—C61—C66122.64 (10)C35—C36—H36119.00
C62—C61—C66118.92 (11)C61—C62—H62120.00
C61—C62—C63120.64 (13)C63—C62—H62120.00
C62—C63—C64120.13 (14)C62—C63—H63120.00
C63—C64—C65119.56 (14)C64—C63—H63120.00
C64—C65—C66120.43 (13)C63—C64—H64120.00
C61—C66—C65120.30 (12)C65—C64—H64120.00
O1—C1—H1117.00C64—C65—H65120.00
N1—C1—H1117.00C66—C65—H65120.00
N1—C2—H2107.00C61—C66—H66120.00
C3—C2—H2107.00C65—C66—H66120.00
C21—C2—H2107.00
C2—N1—C1—O110.3 (2)N1—C6—C61—C6638.97 (15)
C6—N1—C1—O1177.08 (13)C5—C6—C61—C6294.24 (13)
C1—N1—C2—C3128.30 (11)C5—C6—C61—C6684.06 (14)
C1—N1—C2—C21104.00 (13)C3—C13—C31—C32109.37 (14)
C6—N1—C2—C338.20 (13)C3—C13—C31—C3671.24 (15)
C6—N1—C2—C2189.50 (12)C2—C21—C22—C23178.23 (12)
C1—N1—C6—C5176.52 (11)C26—C21—C22—C231.27 (19)
C1—N1—C6—C6152.68 (14)C2—C21—C26—C25178.42 (12)
C2—N1—C6—C516.75 (14)C22—C21—C26—C251.56 (19)
C2—N1—C6—C61140.59 (10)C21—C22—C23—C240.0 (2)
N1—C2—C3—C459.37 (12)C22—C23—C24—C250.9 (2)
N1—C2—C3—C1362.53 (12)C23—C24—C25—C260.6 (2)
C21—C2—C3—C466.94 (12)C24—C25—C26—C210.6 (2)
C21—C2—C3—C13171.17 (9)C13—C31—C32—C33179.22 (14)
N1—C2—C21—C2248.07 (14)C36—C31—C32—C330.2 (2)
N1—C2—C21—C26135.12 (11)C13—C31—C36—C35179.15 (13)
C3—C2—C21—C22172.75 (11)C32—C31—C36—C350.3 (2)
C3—C2—C21—C2610.44 (16)C31—C32—C33—C340.1 (3)
C2—C3—C4—O4155.25 (11)C32—C33—C34—C350.3 (3)
C2—C3—C4—C525.61 (13)C33—C34—C35—C360.2 (2)
C13—C3—C4—O480.12 (14)C34—C35—C36—C310.1 (2)
C13—C3—C4—C599.03 (12)C6—C61—C62—C63177.20 (12)
C2—C3—C13—C3163.87 (13)C66—C61—C62—C631.16 (19)
C4—C3—C13—C31173.40 (10)C6—C61—C66—C65178.53 (12)
O4—C4—C5—C6148.61 (12)C62—C61—C66—C650.24 (19)
C3—C4—C5—C630.55 (14)C61—C62—C63—C641.6 (2)
C4—C5—C6—N152.04 (13)C62—C63—C64—C650.6 (2)
C4—C5—C6—C61177.26 (10)C63—C64—C65—C660.8 (2)
N1—C6—C61—C62142.73 (11)C64—C65—C66—C611.2 (2)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y, z+1; (iii) x+1, y1/2, z+1/2; (iv) x1, y, z; (v) x+1, y+1, z+1; (vi) x+1, y, z; (vii) x, y+1/2, z1/2; (viii) x, y+1/2, z+1/2; (ix) x, y1/2, z+1/2; (x) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24—H24···Cgv0.932.813.651 (1)151
C34—H34···Cgvi0.932.973.890 (2)172
C2—H2···O10.982.412.8175 (15)105
C3—H3···O4ii0.982.443.4093 (15)170
C6—H6···O1iii0.982.293.2576 (16)168
Symmetry codes: (ii) x+1, y, z+1; (iii) x+1, y1/2, z+1/2; (v) x+1, y+1, z+1; (vi) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC25H23NO2
Mr369.44
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)10.5355 (3), 9.3464 (2), 21.0493 (5)
β (°) 101.520 (3)
V3)2030.95 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.41 × 0.37 × 0.29
Data collection
DiffractometerOxford Diffraction Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.969, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
29482, 6871, 3596
Rint0.041
(sin θ/λ)max1)0.756
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.142, 1.00
No. of reflections6871
No. of parameters253
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.47, 0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24—H24···Cgi0.932.813.651 (1)151
C34—H34···Cgii0.932.973.890 (2)172
C2—H2···O10.982.412.8175 (15)105
C3—H3···O4iii0.982.443.4093 (15)170
C6—H6···O1iv0.982.293.2576 (16)168
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x+1, y, z+1; (iv) x+1, y1/2, z+1/2.
 

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