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The crystal structure of the title compound, C38H33NO, shows that the OH group inter­acts with the N atom of the dimethyl­amino group via an intra­molecular hydrogen bond, resulting in the formation of a seven-membered ring. The presence of this inter­action, the poor nucleofugal properties of the hydroxy function and the particularly high steric hindrance decrease the ability of the OH group for substitution by other nucleophiles. The crystal packing exhibits no classical inter­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806056170/cv2168sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806056170/cv2168Isup2.hkl
Contains datablock I

CCDC reference: 636228

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.119
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 30 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.58 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: enCIFer (Allen et al., 2004).

1-[2-(Dimethylaminomethyl)phenyl]-2,3,4,5-tetraphenylcyclopentadien-1-ol top
Crystal data top
C38H33NOZ = 2
Mr = 519.65F(000) = 552
Triclinic, P1Dx = 1.202 Mg m3
Hall symbol: -P 1Melting point: 428 K
a = 10.1507 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1701 (3) ÅCell parameters from 6037 reflections
c = 14.3299 (3) Åθ = 1–27.5°
α = 91.3388 (16)°µ = 0.07 mm1
β = 100.0688 (17)°T = 150 K
γ = 115.4451 (11)°Prism, colourless
V = 1435.69 (6) Å30.4 × 0.25 × 0.18 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
4982 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 27.5°, θmin = 1.5°
Detector resolution: 9.091 pixels mm-1h = 1313
φ and ω scans to fill the Ewald spherek = 1414
23210 measured reflectionsl = 1818
6577 independent 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)] = 0.045Hydrogen site location: difference Fourier map
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0546P)2 + 0.4091P]
where P = (Fo2 + 2Fc2)/3
6577 reflections(Δ/σ)max < 0.001
367 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. Spectroscopic analysis: 1H NMR (CDCl3, δ, p.p.m.): 7.69 (m, 2H), 7.29 (m, 2H), 7.13–7.00 (m, 20H), 3.34 (s, 2H), 1.97 (s, 6H); IR (TlBr disc, ν, cm-1): 3439 (br versus), 3050 (m), 2925 (s), 2847 (m), 2777 (w), 1598 (s), 1574 (m), 1489 (s), 1442 (s), 1368 (w), 1313 (w), 1251 (s), 1174 (s), 1134 (w), 1103 (m), 1072 (m), 1029 (m), 1010 (m), 924 (m), 873 (w), 811 (m), 784 (s), 745 (versus), 698 (versus), 667 (m), 620 (w), 573 (m), 554 (s), 457 (m); Raman (quartz capillary, cm-1): 3061 (m), 3051 (m), 2997 (w), 2960 (m), 2821 (w), 2778 (w), 1632 (m), 1607 (versus), 1598 (s), 1581 (s), 1566 (m), 1497 (m), 1441 (w), 1336 (m), 1326 (m), 1307 (m), 1177 (w), 1156 (w), 1003 (s), 980 (s), 924 (m), 404 (m), 152 (m), 125 (s), 108 (s), 85 (s). Elemental analysis, calculated for C38H33NO: C 87.83, H 6.40, N 2.70%; found: C 88.02, H 6.44, N 2.66%.

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
C10.43538 (14)0.46360 (12)0.18545 (8)0.0215 (3)
C20.58389 (14)0.46480 (12)0.23292 (9)0.0213 (3)
C30.65320 (14)0.56303 (12)0.30562 (9)0.0211 (3)
C40.56418 (14)0.63871 (12)0.31017 (9)0.0213 (3)
C50.44190 (14)0.58764 (12)0.23854 (9)0.0220 (3)
C110.30835 (14)0.33460 (12)0.20779 (9)0.0216 (3)
C120.19779 (14)0.23205 (13)0.14002 (9)0.0247 (3)
C130.09481 (16)0.11987 (14)0.17302 (10)0.0338 (3)
H130.02210.05120.12860.041*
C140.09672 (17)0.10696 (15)0.26840 (11)0.0369 (4)
H140.02660.03100.28780.044*
C150.20399 (16)0.20822 (14)0.33494 (10)0.0303 (3)
H150.20650.20160.39970.036*
C160.30750 (15)0.31942 (13)0.30443 (9)0.0255 (3)
H160.37960.38700.34990.031*
C170.17914 (15)0.23150 (14)0.03303 (9)0.0270 (3)
H17A0.08910.15350.00300.032*
H17B0.16670.30980.01500.032*
C180.32977 (18)0.11478 (15)0.02145 (11)0.0359 (3)
H18A0.23960.03490.00150.054*
H18B0.35800.11970.08950.054*
H18C0.40780.11360.00740.054*
C190.28084 (18)0.23510 (16)0.10642 (10)0.0401 (4)
H19A0.36550.23810.12930.060*
H19B0.26770.31320.12100.060*
H19C0.19330.15690.13680.060*
C210.63257 (14)0.36414 (13)0.20549 (9)0.0247 (3)
C220.67269 (16)0.35842 (15)0.11780 (10)0.0327 (3)
H220.66450.41590.07370.039*
C230.72488 (19)0.26679 (18)0.09629 (13)0.0464 (4)
H230.75250.26390.03800.056*
C240.7360 (2)0.18026 (19)0.16077 (14)0.0545 (5)
H240.77180.11970.14620.065*
C250.6939 (2)0.18334 (18)0.24712 (13)0.0524 (5)
H250.70000.12410.29030.063*
C260.64259 (18)0.27481 (15)0.26905 (11)0.0365 (4)
H260.61440.27660.32720.044*
C310.79909 (14)0.59737 (12)0.36954 (9)0.0225 (3)
C320.81595 (16)0.60790 (13)0.46826 (9)0.0279 (3)
H320.73370.59090.49540.034*
C330.95460 (17)0.64359 (14)0.52677 (10)0.0344 (3)
H330.96480.65020.59270.041*
C341.07694 (17)0.66909 (15)0.48706 (11)0.0363 (4)
H341.16970.69320.52630.044*
C351.06244 (16)0.65899 (15)0.38939 (11)0.0361 (3)
H351.14520.67640.36280.043*
C360.92423 (15)0.62287 (14)0.33098 (10)0.0300 (3)
H360.91480.61550.26510.036*
C410.60974 (14)0.75458 (12)0.38148 (9)0.0221 (3)
C420.74949 (15)0.86359 (13)0.39185 (10)0.0273 (3)
H420.81640.86140.35580.033*
C430.78964 (17)0.97496 (14)0.45527 (11)0.0332 (3)
H430.88221.04770.46070.040*
C440.69194 (18)0.97781 (15)0.51037 (11)0.0365 (4)
H440.71851.05270.55270.044*
C450.55438 (17)0.86916 (15)0.50260 (10)0.0336 (3)
H450.48930.87070.54040.040*
C460.51348 (15)0.75822 (14)0.43874 (9)0.0267 (3)
H460.42100.68550.43400.032*
C510.33635 (14)0.64322 (13)0.20588 (9)0.0241 (3)
C520.38298 (16)0.78141 (14)0.21629 (10)0.0304 (3)
H520.48170.83780.24390.037*
C530.28544 (18)0.83556 (16)0.18632 (11)0.0363 (3)
H530.31820.92740.19550.044*
C540.13909 (18)0.75359 (16)0.14273 (11)0.0369 (4)
H540.07310.78980.12280.044*
C550.09216 (17)0.61756 (16)0.12915 (11)0.0350 (3)
H550.00550.56220.09870.042*
C560.18886 (15)0.56253 (15)0.16035 (10)0.0300 (3)
H560.15510.47060.15090.036*
N10.30531 (13)0.23068 (11)0.00318 (8)0.0279 (3)
O10.42618 (10)0.48103 (9)0.08751 (6)0.0247 (2)
H10.410 (2)0.398 (2)0.0569 (14)0.063 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0218 (6)0.0211 (6)0.0182 (6)0.0068 (5)0.0027 (5)0.0013 (5)
C20.0202 (6)0.0212 (6)0.0208 (6)0.0069 (5)0.0058 (5)0.0027 (5)
C30.0209 (6)0.0208 (6)0.0202 (6)0.0073 (5)0.0056 (5)0.0029 (5)
C40.0219 (6)0.0183 (6)0.0213 (6)0.0060 (5)0.0061 (5)0.0021 (5)
C50.0212 (6)0.0198 (6)0.0230 (6)0.0064 (5)0.0066 (5)0.0036 (5)
C110.0204 (6)0.0200 (6)0.0234 (6)0.0080 (5)0.0046 (5)0.0026 (5)
C120.0220 (7)0.0239 (6)0.0245 (6)0.0069 (5)0.0046 (5)0.0014 (5)
C130.0283 (7)0.0266 (7)0.0331 (8)0.0003 (6)0.0073 (6)0.0017 (6)
C140.0361 (8)0.0276 (7)0.0368 (8)0.0012 (6)0.0161 (7)0.0054 (6)
C150.0348 (8)0.0311 (7)0.0262 (7)0.0132 (6)0.0122 (6)0.0060 (6)
C160.0255 (7)0.0249 (7)0.0238 (6)0.0090 (6)0.0048 (5)0.0013 (5)
C170.0232 (7)0.0244 (7)0.0242 (7)0.0039 (6)0.0001 (5)0.0006 (5)
C180.0375 (8)0.0282 (7)0.0382 (8)0.0108 (7)0.0090 (7)0.0015 (6)
C190.0421 (9)0.0341 (8)0.0237 (7)0.0020 (7)0.0073 (6)0.0012 (6)
C210.0205 (6)0.0232 (6)0.0253 (7)0.0067 (5)0.0007 (5)0.0046 (5)
C220.0296 (8)0.0331 (8)0.0312 (7)0.0099 (6)0.0074 (6)0.0041 (6)
C230.0414 (9)0.0525 (10)0.0467 (10)0.0227 (8)0.0100 (7)0.0165 (8)
C240.0570 (12)0.0545 (11)0.0597 (12)0.0394 (10)0.0051 (9)0.0214 (9)
C250.0718 (13)0.0457 (10)0.0475 (10)0.0411 (10)0.0076 (9)0.0061 (8)
C260.0465 (9)0.0341 (8)0.0301 (8)0.0220 (7)0.0002 (7)0.0022 (6)
C310.0232 (7)0.0182 (6)0.0242 (6)0.0088 (5)0.0014 (5)0.0010 (5)
C320.0309 (7)0.0261 (7)0.0255 (7)0.0129 (6)0.0025 (5)0.0014 (5)
C330.0434 (9)0.0295 (7)0.0268 (7)0.0181 (7)0.0062 (6)0.0036 (6)
C340.0298 (8)0.0284 (7)0.0429 (9)0.0130 (6)0.0114 (6)0.0059 (6)
C350.0234 (7)0.0339 (8)0.0464 (9)0.0104 (6)0.0026 (6)0.0018 (7)
C360.0255 (7)0.0319 (7)0.0289 (7)0.0102 (6)0.0036 (6)0.0003 (6)
C410.0234 (7)0.0204 (6)0.0223 (6)0.0103 (5)0.0021 (5)0.0019 (5)
C420.0259 (7)0.0234 (7)0.0306 (7)0.0091 (6)0.0057 (5)0.0030 (5)
C430.0332 (8)0.0198 (7)0.0384 (8)0.0074 (6)0.0009 (6)0.0000 (6)
C440.0488 (9)0.0261 (7)0.0342 (8)0.0195 (7)0.0002 (7)0.0055 (6)
C450.0426 (9)0.0349 (8)0.0308 (7)0.0235 (7)0.0096 (6)0.0006 (6)
C460.0267 (7)0.0248 (7)0.0286 (7)0.0115 (6)0.0054 (5)0.0024 (5)
C510.0245 (7)0.0272 (7)0.0213 (6)0.0115 (6)0.0057 (5)0.0029 (5)
C520.0294 (7)0.0274 (7)0.0317 (7)0.0114 (6)0.0019 (6)0.0045 (6)
C530.0425 (9)0.0320 (8)0.0380 (8)0.0212 (7)0.0032 (7)0.0069 (6)
C540.0389 (9)0.0478 (9)0.0345 (8)0.0290 (8)0.0060 (7)0.0092 (7)
C550.0249 (7)0.0453 (9)0.0345 (8)0.0169 (7)0.0022 (6)0.0015 (7)
C560.0251 (7)0.0307 (7)0.0322 (7)0.0110 (6)0.0046 (6)0.0002 (6)
N10.0297 (6)0.0249 (6)0.0213 (5)0.0050 (5)0.0051 (5)0.0004 (4)
O10.0280 (5)0.0217 (5)0.0187 (4)0.0064 (4)0.0033 (4)0.0022 (4)
Geometric parameters (Å, º) top
C1—O11.4138 (15)C24—C251.382 (3)
C1—C51.5353 (17)C24—H240.9300
C1—C21.5360 (18)C25—C261.383 (2)
C1—C111.5527 (17)C25—H250.9300
C2—C31.3458 (17)C26—H260.9300
C2—C211.4790 (18)C31—C321.3910 (18)
C3—C311.4834 (18)C31—C361.3935 (19)
C3—C41.4866 (18)C32—C331.390 (2)
C4—C51.3559 (18)C32—H320.9300
C4—C411.4805 (17)C33—C341.378 (2)
C5—C511.4704 (19)C33—H330.9300
C11—C161.4003 (18)C34—C351.378 (2)
C11—C121.4060 (17)C34—H340.9300
C12—C131.4006 (19)C35—C361.385 (2)
C12—C171.5111 (18)C35—H350.9300
C13—C141.375 (2)C36—H360.9300
C13—H130.9300C41—C461.3937 (18)
C14—C151.379 (2)C41—C421.3967 (18)
C14—H140.9300C42—C431.3861 (19)
C15—C161.3793 (19)C42—H420.9300
C15—H150.9300C43—C441.381 (2)
C16—H160.9300C43—H430.9300
C17—N11.4669 (18)C44—C451.385 (2)
C17—H17A0.9700C44—H440.9300
C17—H17B0.9700C45—C461.3847 (19)
C18—N11.4592 (19)C45—H450.9300
C18—H18A0.9600C46—H460.9300
C18—H18B0.9600C51—C561.3968 (19)
C18—H18C0.9600C51—C521.4021 (19)
C19—N11.4623 (17)C52—C531.381 (2)
C19—H19A0.9600C52—H520.9300
C19—H19B0.9600C53—C541.384 (2)
C19—H19C0.9600C53—H530.9300
C21—C261.390 (2)C54—C551.380 (2)
C21—C221.3952 (19)C54—H540.9300
C22—C231.390 (2)C55—C561.385 (2)
C22—H220.9300C55—H550.9300
C23—C241.378 (3)C56—H560.9300
C23—H230.9300O1—H10.95 (2)
O1—C1—C5108.35 (10)C25—C24—H24120.0
O1—C1—C2112.76 (10)C24—C25—C26119.73 (17)
C5—C1—C2102.06 (10)C24—C25—H25120.1
O1—C1—C11114.75 (10)C26—C25—H25120.1
C5—C1—C11110.80 (10)C25—C26—C21121.03 (15)
C2—C1—C11107.39 (10)C25—C26—H26119.5
C3—C2—C21126.81 (12)C21—C26—H26119.5
C3—C2—C1109.60 (11)C32—C31—C36118.38 (12)
C21—C2—C1123.40 (10)C32—C31—C3121.64 (12)
C2—C3—C31126.51 (12)C36—C31—C3119.96 (11)
C2—C3—C4109.40 (11)C33—C32—C31120.61 (14)
C31—C3—C4124.03 (11)C33—C32—H32119.7
C5—C4—C41127.01 (12)C31—C32—H32119.7
C5—C4—C3109.56 (11)C34—C33—C32119.98 (14)
C41—C4—C3123.40 (11)C34—C33—H33120.0
C4—C5—C51128.44 (12)C32—C33—H33120.0
C4—C5—C1109.00 (11)C33—C34—C35120.26 (13)
C51—C5—C1122.27 (11)C33—C34—H34119.9
C16—C11—C12117.97 (12)C35—C34—H34119.9
C16—C11—C1116.21 (11)C34—C35—C36119.83 (14)
C12—C11—C1125.81 (11)C34—C35—H35120.1
C13—C12—C11118.19 (12)C36—C35—H35120.1
C13—C12—C17116.18 (12)C35—C36—C31120.92 (13)
C11—C12—C17125.64 (12)C35—C36—H36119.5
C14—C13—C12122.76 (13)C31—C36—H36119.5
C14—C13—H13118.6C46—C41—C42118.54 (12)
C12—C13—H13118.6C46—C41—C4120.81 (12)
C13—C14—C15119.12 (13)C42—C41—C4120.65 (12)
C13—C14—H14120.4C43—C42—C41120.76 (13)
C15—C14—H14120.4C43—C42—H42119.6
C16—C15—C14119.35 (13)C41—C42—H42119.6
C16—C15—H15120.3C44—C43—C42119.93 (14)
C14—C15—H15120.3C44—C43—H43120.0
C15—C16—C11122.61 (12)C42—C43—H43120.0
C15—C16—H16118.7C43—C44—C45119.99 (13)
C11—C16—H16118.7C43—C44—H44120.0
N1—C17—C12113.43 (11)C45—C44—H44120.0
N1—C17—H17A108.9C46—C45—C44120.21 (14)
C12—C17—H17A108.9C46—C45—H45119.9
N1—C17—H17B108.9C44—C45—H45119.9
C12—C17—H17B108.9C45—C46—C41120.54 (13)
H17A—C17—H17B107.7C45—C46—H46119.7
N1—C18—H18A109.5C41—C46—H46119.7
N1—C18—H18B109.5C56—C51—C52117.40 (13)
H18A—C18—H18B109.5C56—C51—C5122.03 (12)
N1—C18—H18C109.5C52—C51—C5120.52 (12)
H18A—C18—H18C109.5C53—C52—C51121.40 (14)
H18B—C18—H18C109.5C53—C52—H52119.3
N1—C19—H19A109.5C51—C52—H52119.3
N1—C19—H19B109.5C52—C53—C54120.21 (14)
H19A—C19—H19B109.5C52—C53—H53119.9
N1—C19—H19C109.5C54—C53—H53119.9
H19A—C19—H19C109.5C55—C54—C53119.28 (14)
H19B—C19—H19C109.5C55—C54—H54120.4
C26—C21—C22118.73 (13)C53—C54—H54120.4
C26—C21—C2119.68 (12)C54—C55—C56120.77 (14)
C22—C21—C2121.57 (13)C54—C55—H55119.6
C23—C22—C21120.02 (15)C56—C55—H55119.6
C23—C22—H22120.0C55—C56—C51120.89 (14)
C21—C22—H22120.0C55—C56—H56119.6
C24—C23—C22120.40 (16)C51—C56—H56119.6
C24—C23—H23119.8C18—N1—C19110.77 (12)
C22—C23—H23119.8C18—N1—C17111.60 (11)
C23—C24—C25120.08 (16)C19—N1—C17109.89 (12)
C23—C24—H24120.0C1—O1—H1105.0 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.95 (2)1.80 (2)2.7089 (14)157.6 (18)
Selected geometric parameters (Å, °). top
C1—C21.536 (2)Cp—Ph188.38 (8)
C2—C31.3458 (18)Cp—Ph265.43 (8)
C3—C41.487 (2)Cp—Ph356.26 (7)
C1—O11.4138 (14)Cp—Ph454.26 (7)
C2—C1—C5102.06 (10)Cp—Ph532.59 (7)
O1—C1—C11114.76 (10)
Cp is the cyclopentadiene ring plane defined by atoms C1–C5. Ph1, Ph2, Ph3, Ph4 and Ph5 are the aromatic ring planes defined by atoms C11–C16, C21–C26, C31–C36, C41–C46 and C51–C56, respectively.
 

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