The title compound, C
19H
25NO, 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
CCDC reference: 274653
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.042
- wR factor = 0.086
- Data-to-parameter ratio = 10.3
checkCIF/PLATON results
No syntax errors found
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
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
C19H25NO | F(000) = 616 |
Mr = 283.40 | Dx = 1.151 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3577 reflections |
a = 12.706 (3) Å | θ = 2.4–27.5° |
b = 11.141 (2) Å | µ = 0.07 mm−1 |
c = 11.552 (2) Å | T = 293 K |
V = 1635.4 (6) Å3 | Prism, yellow |
Z = 4 | 0.33 × 0.32 × 0.28 mm |
Data collection top
Rigaku R-AXIS-RAPID imaging-plate diffractometer | 1968 independent reflections |
Radiation source: fine-focus sealed tube | 1004 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.977, Tmax = 0.981 | k = −14→14 |
3578 measured reflections | l = −14→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-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 reflections | Δρmax = 0.13 e Å−3 |
192 parameters | Δρmin = −0.11 e Å−3 |
32 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.86642 (17) | 0.8896 (2) | 0.9217 (2) | 0.0734 (7) | |
H1 | 0.9192 | 0.9225 | 0.9643 | 0.100 (13)* | |
N1 | 0.50831 (18) | 0.5114 (2) | 1.0777 (2) | 0.0579 (7) | |
C1 | 0.6610 (2) | 0.6425 (2) | 1.0668 (3) | 0.0513 (7) | |
C2 | 0.6392 (2) | 0.7017 (3) | 0.9645 (3) | 0.0661 (10) | |
H2 | 0.5754 | 0.6821 | 0.9241 | 0.079* | |
C3 | 0.7075 (3) | 0.7846 (3) | 0.9185 (3) | 0.0665 (9) | |
H3 | 0.6900 | 0.8261 | 0.8483 | 0.080* | |
C4 | 0.8008 (2) | 0.8093 (3) | 0.9733 (3) | 0.0558 (8) | |
C5 | 0.8244 (2) | 0.7530 (3) | 1.0754 (3) | 0.0652 (9) | |
H5 | 0.8897 | 0.7704 | 1.1136 | 0.078* | |
C6 | 0.7546 (2) | 0.6713 (3) | 1.1217 (3) | 0.0622 (9) | |
H6 | 0.7715 | 0.6332 | 1.1939 | 0.075* | |
C7 | 0.5956 (2) | 0.5485 (3) | 1.1177 (3) | 0.0575 (8) | |
H7 | 0.6199 | 0.5105 | 1.1873 | 0.069* | |
C8 | 0.4654 (2) | 0.2950 (3) | 1.0569 (3) | 0.0537 (8) | |
C9 | 0.5783 (2) | 0.2621 (4) | 1.0361 (4) | 0.1029 (15) | |
H9A | 0.6145 | 0.3242 | 0.9944 | 0.124* | |
H9B | 0.6111 | 0.2530 | 1.1105 | 0.124* | |
C10 | 0.5860 (3) | 0.1472 (5) | 0.9650 (6) | 0.1194 (18) | |
H10 | 0.6589 | 0.1288 | 0.9526 | 0.143* | |
C11 | 0.5391 (4) | 0.0451 (4) | 1.0282 (5) | 0.1264 (18) | |
H11A | 0.5447 | −0.0260 | 0.9816 | 0.152* | |
H11B | 0.5741 | 0.0310 | 1.1006 | 0.152* | |
C12 | 0.4293 (4) | 0.0731 (4) | 1.0506 (5) | 0.1149 (16) | |
H12 | 0.3985 | 0.0087 | 1.0942 | 0.138* | |
C13 | 0.3715 (3) | 0.0867 (4) | 0.9413 (6) | 0.1199 (18) | |
H13A | 0.3748 | 0.0136 | 0.8974 | 0.144* | |
H13B | 0.2991 | 0.1023 | 0.9597 | 0.144* | |
C14 | 0.4151 (5) | 0.1908 (4) | 0.8719 (4) | 0.1219 (18) | |
H14 | 0.3790 | 0.1992 | 0.7994 | 0.146* | |
C15 | 0.4100 (4) | 0.3068 (4) | 0.9425 (3) | 0.1029 (14) | |
H15A | 0.3377 | 0.3277 | 0.9559 | 0.123* | |
H15B | 0.4418 | 0.3709 | 0.8994 | 0.123* | |
C16 | 0.5339 (5) | 0.1664 (5) | 0.8495 (5) | 0.138 (2) | |
H16A | 0.5667 | 0.2343 | 0.8133 | 0.165* | |
H16B | 0.5438 | 0.0977 | 0.8005 | 0.165* | |
C17 | 0.4174 (3) | 0.1885 (3) | 1.1210 (4) | 0.1011 (13) | |
H17A | 0.4540 | 0.1790 | 1.1931 | 0.121* | |
H17B | 0.3445 | 0.2031 | 1.1379 | 0.121* | |
C18 | 0.4589 (2) | 0.4079 (3) | 1.1354 (3) | 0.0609 (9) | |
H18 | 0.4986 | 0.3908 | 1.2041 | 0.073* | |
C19 | 0.3480 (2) | 0.4445 (3) | 1.1738 (3) | 0.0828 (12) | |
H19A | 0.3525 | 0.5142 | 1.2224 | 0.124* | |
H19B | 0.3158 | 0.3800 | 1.2161 | 0.124* | |
H19C | 0.3063 | 0.4626 | 1.1068 | 0.124* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0706 (15) | 0.0849 (16) | 0.0646 (15) | −0.0192 (13) | −0.0139 (13) | −0.0023 (14) |
N1 | 0.0502 (14) | 0.0645 (16) | 0.0590 (17) | −0.0012 (12) | −0.0064 (14) | 0.0043 (15) |
C1 | 0.0485 (17) | 0.0521 (17) | 0.053 (2) | 0.0053 (15) | −0.0087 (17) | −0.0125 (18) |
C2 | 0.060 (2) | 0.081 (2) | 0.058 (2) | −0.009 (2) | −0.0166 (18) | −0.001 (2) |
C3 | 0.065 (2) | 0.077 (2) | 0.058 (2) | −0.0085 (19) | −0.0223 (19) | 0.0073 (19) |
C4 | 0.054 (2) | 0.060 (2) | 0.053 (2) | −0.0006 (17) | −0.0025 (18) | −0.0121 (19) |
C5 | 0.0518 (19) | 0.072 (2) | 0.072 (3) | −0.0008 (17) | −0.0244 (19) | −0.002 (2) |
C6 | 0.058 (2) | 0.062 (2) | 0.066 (2) | 0.0063 (18) | −0.0148 (19) | 0.0027 (19) |
C7 | 0.060 (2) | 0.061 (2) | 0.052 (2) | 0.0082 (18) | −0.0109 (18) | −0.0010 (18) |
C8 | 0.0398 (16) | 0.063 (2) | 0.058 (2) | −0.0001 (14) | 0.0110 (16) | 0.004 (2) |
C9 | 0.054 (2) | 0.108 (3) | 0.146 (4) | 0.005 (2) | 0.018 (3) | −0.039 (3) |
C10 | 0.060 (2) | 0.116 (4) | 0.183 (6) | 0.010 (3) | 0.043 (3) | −0.035 (4) |
C11 | 0.140 (5) | 0.097 (4) | 0.143 (5) | 0.038 (3) | −0.010 (4) | −0.018 (3) |
C12 | 0.140 (4) | 0.080 (3) | 0.124 (5) | −0.037 (3) | 0.034 (4) | 0.008 (4) |
C13 | 0.073 (3) | 0.087 (4) | 0.200 (6) | 0.000 (2) | −0.007 (4) | −0.037 (4) |
C14 | 0.181 (6) | 0.097 (4) | 0.088 (3) | 0.054 (4) | −0.047 (3) | −0.021 (3) |
C15 | 0.141 (4) | 0.088 (3) | 0.079 (3) | 0.034 (3) | −0.042 (3) | −0.013 (3) |
C16 | 0.219 (7) | 0.089 (4) | 0.105 (5) | −0.037 (4) | 0.089 (5) | −0.022 (3) |
C17 | 0.125 (3) | 0.087 (3) | 0.092 (3) | −0.022 (3) | 0.042 (3) | 0.004 (3) |
C18 | 0.0544 (19) | 0.073 (2) | 0.0553 (19) | 0.0041 (17) | −0.0028 (17) | 0.0118 (19) |
C19 | 0.072 (2) | 0.087 (3) | 0.089 (3) | 0.012 (2) | 0.027 (2) | 0.002 (2) |
Geometric parameters (Å, º) top
O1—C4 | 1.360 (3) | C10—H10 | 0.9602 |
O1—H1 | 0.9088 | C11—C12 | 1.452 (5) |
N1—C7 | 1.270 (3) | C11—H11A | 0.9601 |
N1—C18 | 1.472 (4) | C11—H11B | 0.9600 |
C1—C2 | 1.382 (4) | C12—C13 | 1.469 (5) |
C1—C6 | 1.386 (4) | C12—C17 | 1.530 (5) |
C1—C7 | 1.460 (4) | C12—H12 | 0.9598 |
C2—C3 | 1.374 (4) | C13—C14 | 1.515 (5) |
C2—H2 | 0.9599 | C13—H13A | 0.9599 |
C3—C4 | 1.372 (4) | C13—H13B | 0.9601 |
C3—H3 | 0.9599 | C14—C15 | 1.530 (4) |
C4—C5 | 1.370 (4) | C14—C16 | 1.556 (6) |
C5—C6 | 1.379 (4) | C14—H14 | 0.9599 |
C5—H5 | 0.9600 | C15—H15A | 0.9600 |
C6—H6 | 0.9599 | C15—H15B | 0.9601 |
C7—H7 | 0.9599 | C16—H16A | 0.9600 |
C8—C9 | 1.501 (3) | C16—H16B | 0.9600 |
C8—C15 | 1.503 (4) | C17—H17A | 0.9600 |
C8—C17 | 1.526 (4) | C17—H17B | 0.9600 |
C8—C18 | 1.553 (4) | C18—C19 | 1.532 (4) |
C9—C10 | 1.524 (5) | C18—H18 | 0.9600 |
C9—H9A | 0.9600 | C19—H19A | 0.9600 |
C9—H9B | 0.9599 | C19—H19B | 0.9597 |
C10—C11 | 1.478 (5) | C19—H19C | 0.9600 |
C10—C16 | 1.505 (6) | | |
| | | |
C4—O1—H1 | 118.7 | C11—C12—C17 | 111.8 (4) |
C7—N1—C18 | 117.6 (3) | C13—C12—C17 | 108.7 (4) |
C2—C1—C6 | 116.9 (3) | C11—C12—H12 | 109.0 |
C2—C1—C7 | 124.9 (3) | C13—C12—H12 | 108.9 |
C6—C1—C7 | 118.0 (3) | C17—C12—H12 | 107.9 |
C3—C2—C1 | 121.7 (3) | C12—C13—C14 | 110.5 (4) |
C3—C2—H2 | 119.9 | C12—C13—H13A | 110.1 |
C1—C2—H2 | 118.5 | C14—C13—H13A | 110.7 |
C4—C3—C2 | 120.2 (3) | C12—C13—H13B | 108.0 |
C4—C3—H3 | 119.5 | C14—C13—H13B | 109.2 |
C2—C3—H3 | 120.3 | H13A—C13—H13B | 108.2 |
O1—C4—C5 | 123.0 (3) | C13—C14—C15 | 110.4 (4) |
O1—C4—C3 | 117.4 (3) | C13—C14—C16 | 108.0 (4) |
C5—C4—C3 | 119.6 (3) | C15—C14—C16 | 106.2 (4) |
C4—C5—C6 | 119.8 (3) | C13—C14—H14 | 111.2 |
C4—C5—H5 | 119.5 | C15—C14—H14 | 111.3 |
C6—C5—H5 | 120.8 | C16—C14—H14 | 109.6 |
C5—C6—C1 | 121.8 (3) | C8—C15—C14 | 112.0 (3) |
C5—C6—H6 | 119.0 | C8—C15—H15A | 109.1 |
C1—C6—H6 | 119.2 | C14—C15—H15A | 109.3 |
N1—C7—C1 | 125.7 (3) | C8—C15—H15B | 108.9 |
N1—C7—H7 | 116.2 | C14—C15—H15B | 109.5 |
C1—C7—H7 | 118.1 | H15A—C15—H15B | 107.9 |
C9—C8—C15 | 109.2 (3) | C10—C16—C14 | 107.7 (3) |
C9—C8—C17 | 105.7 (3) | C10—C16—H16A | 107.9 |
C15—C8—C17 | 107.9 (3) | C14—C16—H16A | 110.8 |
C9—C8—C18 | 110.0 (2) | C10—C16—H16B | 110.6 |
C15—C8—C18 | 114.7 (2) | C14—C16—H16B | 111.4 |
C17—C8—C18 | 109.0 (3) | H16A—C16—H16B | 108.4 |
C8—C9—C10 | 110.6 (3) | C8—C17—C12 | 110.8 (3) |
C8—C9—H9A | 111.2 | C8—C17—H17A | 108.2 |
C10—C9—H9A | 107.8 | C12—C17—H17A | 108.7 |
C8—C9—H9B | 107.3 | C8—C17—H17B | 110.6 |
C10—C9—H9B | 111.4 | C12—C17—H17B | 110.2 |
H9A—C9—H9B | 108.5 | H17A—C17—H17B | 108.1 |
C11—C10—C16 | 111.7 (4) | N1—C18—C19 | 108.4 (3) |
C11—C10—C9 | 110.8 (4) | N1—C18—C8 | 110.3 (3) |
C16—C10—C9 | 109.3 (4) | C19—C18—C8 | 115.7 (2) |
C11—C10—H10 | 107.4 | N1—C18—H18 | 107.8 |
C16—C10—H10 | 108.8 | C19—C18—H18 | 107.2 |
C9—C10—H10 | 108.7 | C8—C18—H18 | 107.1 |
C12—C11—C10 | 108.1 (4) | C18—C19—H19A | 109.3 |
C12—C11—H11A | 110.4 | C18—C19—H19B | 109.9 |
C10—C11—H11A | 109.1 | H19A—C19—H19B | 109.5 |
C12—C11—H11B | 109.0 | C18—C19—H19C | 109.2 |
C10—C11—H11B | 111.6 | H19A—C19—H19C | 109.5 |
H11A—C11—H11B | 108.6 | H19B—C19—H19C | 109.5 |
C11—C12—C13 | 110.5 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.91 | 1.88 | 2.778 (3) | 168 |
Symmetry code: (i) x+1/2, −y+3/2, z. |