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The title compound, C19H25NO, a Schiff base, crystallized in the phenol–imine tautomeric form. The C=N bond length is 1.270 (3) Å and the bond length between the C atom of the aromatic ring and the C atom of the imine group is 1.460 (4) Å, which corresponds to a conjugated C=N group. In the crystal structure, a one-dimensional chain is formed via a strong inter­molecular O—H...N hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014935/su6200sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014935/su6200Isup2.hkl
Contains datablock I

CCDC reference: 274653

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.042
  • wR factor = 0.086
  • Data-to-parameter ratio = 10.3

checkCIF/PLATON results

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Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C8
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 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.69 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C18 .. 5.02 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 1968 Count of symmetry unique reflns 1968 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXTL/PC.

4-{[1-(1-Adamantyl)ethyl]iminomethyl}phenol top
Crystal data top
C19H25NOF(000) = 616
Mr = 283.40Dx = 1.151 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3577 reflections
a = 12.706 (3) Åθ = 2.4–27.5°
b = 11.141 (2) ŵ = 0.07 mm1
c = 11.552 (2) ÅT = 293 K
V = 1635.4 (6) Å3Prism, yellow
Z = 40.33 × 0.32 × 0.28 mm
Data collection top
Rigaku R-AXIS-RAPID imaging-plate
diffractometer
1968 independent reflections
Radiation source: fine-focus sealed tube1004 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.977, Tmax = 0.981k = 1414
3578 measured reflectionsl = 1415
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)] = 0.042H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0262P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
1968 reflectionsΔρmax = 0.13 e Å3
192 parametersΔρmin = 0.11 e Å3
32 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0083 (9)
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
O10.86642 (17)0.8896 (2)0.9217 (2)0.0734 (7)
H10.91920.92250.96430.100 (13)*
N10.50831 (18)0.5114 (2)1.0777 (2)0.0579 (7)
C10.6610 (2)0.6425 (2)1.0668 (3)0.0513 (7)
C20.6392 (2)0.7017 (3)0.9645 (3)0.0661 (10)
H20.57540.68210.92410.079*
C30.7075 (3)0.7846 (3)0.9185 (3)0.0665 (9)
H30.69000.82610.84830.080*
C40.8008 (2)0.8093 (3)0.9733 (3)0.0558 (8)
C50.8244 (2)0.7530 (3)1.0754 (3)0.0652 (9)
H50.88970.77041.11360.078*
C60.7546 (2)0.6713 (3)1.1217 (3)0.0622 (9)
H60.77150.63321.19390.075*
C70.5956 (2)0.5485 (3)1.1177 (3)0.0575 (8)
H70.61990.51051.18730.069*
C80.4654 (2)0.2950 (3)1.0569 (3)0.0537 (8)
C90.5783 (2)0.2621 (4)1.0361 (4)0.1029 (15)
H9A0.61450.32420.99440.124*
H9B0.61110.25301.11050.124*
C100.5860 (3)0.1472 (5)0.9650 (6)0.1194 (18)
H100.65890.12880.95260.143*
C110.5391 (4)0.0451 (4)1.0282 (5)0.1264 (18)
H11A0.54470.02600.98160.152*
H11B0.57410.03101.10060.152*
C120.4293 (4)0.0731 (4)1.0506 (5)0.1149 (16)
H120.39850.00871.09420.138*
C130.3715 (3)0.0867 (4)0.9413 (6)0.1199 (18)
H13A0.37480.01360.89740.144*
H13B0.29910.10230.95970.144*
C140.4151 (5)0.1908 (4)0.8719 (4)0.1219 (18)
H140.37900.19920.79940.146*
C150.4100 (4)0.3068 (4)0.9425 (3)0.1029 (14)
H15A0.33770.32770.95590.123*
H15B0.44180.37090.89940.123*
C160.5339 (5)0.1664 (5)0.8495 (5)0.138 (2)
H16A0.56670.23430.81330.165*
H16B0.54380.09770.80050.165*
C170.4174 (3)0.1885 (3)1.1210 (4)0.1011 (13)
H17A0.45400.17901.19310.121*
H17B0.34450.20311.13790.121*
C180.4589 (2)0.4079 (3)1.1354 (3)0.0609 (9)
H180.49860.39081.20410.073*
C190.3480 (2)0.4445 (3)1.1738 (3)0.0828 (12)
H19A0.35250.51421.22240.124*
H19B0.31580.38001.21610.124*
H19C0.30630.46261.10680.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0706 (15)0.0849 (16)0.0646 (15)0.0192 (13)0.0139 (13)0.0023 (14)
N10.0502 (14)0.0645 (16)0.0590 (17)0.0012 (12)0.0064 (14)0.0043 (15)
C10.0485 (17)0.0521 (17)0.053 (2)0.0053 (15)0.0087 (17)0.0125 (18)
C20.060 (2)0.081 (2)0.058 (2)0.009 (2)0.0166 (18)0.001 (2)
C30.065 (2)0.077 (2)0.058 (2)0.0085 (19)0.0223 (19)0.0073 (19)
C40.054 (2)0.060 (2)0.053 (2)0.0006 (17)0.0025 (18)0.0121 (19)
C50.0518 (19)0.072 (2)0.072 (3)0.0008 (17)0.0244 (19)0.002 (2)
C60.058 (2)0.062 (2)0.066 (2)0.0063 (18)0.0148 (19)0.0027 (19)
C70.060 (2)0.061 (2)0.052 (2)0.0082 (18)0.0109 (18)0.0010 (18)
C80.0398 (16)0.063 (2)0.058 (2)0.0001 (14)0.0110 (16)0.004 (2)
C90.054 (2)0.108 (3)0.146 (4)0.005 (2)0.018 (3)0.039 (3)
C100.060 (2)0.116 (4)0.183 (6)0.010 (3)0.043 (3)0.035 (4)
C110.140 (5)0.097 (4)0.143 (5)0.038 (3)0.010 (4)0.018 (3)
C120.140 (4)0.080 (3)0.124 (5)0.037 (3)0.034 (4)0.008 (4)
C130.073 (3)0.087 (4)0.200 (6)0.000 (2)0.007 (4)0.037 (4)
C140.181 (6)0.097 (4)0.088 (3)0.054 (4)0.047 (3)0.021 (3)
C150.141 (4)0.088 (3)0.079 (3)0.034 (3)0.042 (3)0.013 (3)
C160.219 (7)0.089 (4)0.105 (5)0.037 (4)0.089 (5)0.022 (3)
C170.125 (3)0.087 (3)0.092 (3)0.022 (3)0.042 (3)0.004 (3)
C180.0544 (19)0.073 (2)0.0553 (19)0.0041 (17)0.0028 (17)0.0118 (19)
C190.072 (2)0.087 (3)0.089 (3)0.012 (2)0.027 (2)0.002 (2)
Geometric parameters (Å, º) top
O1—C41.360 (3)C10—H100.9602
O1—H10.9088C11—C121.452 (5)
N1—C71.270 (3)C11—H11A0.9601
N1—C181.472 (4)C11—H11B0.9600
C1—C21.382 (4)C12—C131.469 (5)
C1—C61.386 (4)C12—C171.530 (5)
C1—C71.460 (4)C12—H120.9598
C2—C31.374 (4)C13—C141.515 (5)
C2—H20.9599C13—H13A0.9599
C3—C41.372 (4)C13—H13B0.9601
C3—H30.9599C14—C151.530 (4)
C4—C51.370 (4)C14—C161.556 (6)
C5—C61.379 (4)C14—H140.9599
C5—H50.9600C15—H15A0.9600
C6—H60.9599C15—H15B0.9601
C7—H70.9599C16—H16A0.9600
C8—C91.501 (3)C16—H16B0.9600
C8—C151.503 (4)C17—H17A0.9600
C8—C171.526 (4)C17—H17B0.9600
C8—C181.553 (4)C18—C191.532 (4)
C9—C101.524 (5)C18—H180.9600
C9—H9A0.9600C19—H19A0.9600
C9—H9B0.9599C19—H19B0.9597
C10—C111.478 (5)C19—H19C0.9600
C10—C161.505 (6)
C4—O1—H1118.7C11—C12—C17111.8 (4)
C7—N1—C18117.6 (3)C13—C12—C17108.7 (4)
C2—C1—C6116.9 (3)C11—C12—H12109.0
C2—C1—C7124.9 (3)C13—C12—H12108.9
C6—C1—C7118.0 (3)C17—C12—H12107.9
C3—C2—C1121.7 (3)C12—C13—C14110.5 (4)
C3—C2—H2119.9C12—C13—H13A110.1
C1—C2—H2118.5C14—C13—H13A110.7
C4—C3—C2120.2 (3)C12—C13—H13B108.0
C4—C3—H3119.5C14—C13—H13B109.2
C2—C3—H3120.3H13A—C13—H13B108.2
O1—C4—C5123.0 (3)C13—C14—C15110.4 (4)
O1—C4—C3117.4 (3)C13—C14—C16108.0 (4)
C5—C4—C3119.6 (3)C15—C14—C16106.2 (4)
C4—C5—C6119.8 (3)C13—C14—H14111.2
C4—C5—H5119.5C15—C14—H14111.3
C6—C5—H5120.8C16—C14—H14109.6
C5—C6—C1121.8 (3)C8—C15—C14112.0 (3)
C5—C6—H6119.0C8—C15—H15A109.1
C1—C6—H6119.2C14—C15—H15A109.3
N1—C7—C1125.7 (3)C8—C15—H15B108.9
N1—C7—H7116.2C14—C15—H15B109.5
C1—C7—H7118.1H15A—C15—H15B107.9
C9—C8—C15109.2 (3)C10—C16—C14107.7 (3)
C9—C8—C17105.7 (3)C10—C16—H16A107.9
C15—C8—C17107.9 (3)C14—C16—H16A110.8
C9—C8—C18110.0 (2)C10—C16—H16B110.6
C15—C8—C18114.7 (2)C14—C16—H16B111.4
C17—C8—C18109.0 (3)H16A—C16—H16B108.4
C8—C9—C10110.6 (3)C8—C17—C12110.8 (3)
C8—C9—H9A111.2C8—C17—H17A108.2
C10—C9—H9A107.8C12—C17—H17A108.7
C8—C9—H9B107.3C8—C17—H17B110.6
C10—C9—H9B111.4C12—C17—H17B110.2
H9A—C9—H9B108.5H17A—C17—H17B108.1
C11—C10—C16111.7 (4)N1—C18—C19108.4 (3)
C11—C10—C9110.8 (4)N1—C18—C8110.3 (3)
C16—C10—C9109.3 (4)C19—C18—C8115.7 (2)
C11—C10—H10107.4N1—C18—H18107.8
C16—C10—H10108.8C19—C18—H18107.2
C9—C10—H10108.7C8—C18—H18107.1
C12—C11—C10108.1 (4)C18—C19—H19A109.3
C12—C11—H11A110.4C18—C19—H19B109.9
C10—C11—H11A109.1H19A—C19—H19B109.5
C12—C11—H11B109.0C18—C19—H19C109.2
C10—C11—H11B111.6H19A—C19—H19C109.5
H11A—C11—H11B108.6H19B—C19—H19C109.5
C11—C12—C13110.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.911.882.778 (3)168
Symmetry code: (i) x+1/2, y+3/2, z.
 

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