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In the title mol­ecule, C23H25NO, the hydroxy H atom is involved in the formation of an intramolecular O—H...N hydrogen bond. The dihedral angle between the benzene ring and the 2-naphthol system is 78.1 (1)°. The crystal packing is stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002035/cv6451sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002035/cv6451Isup2.hkl
Contains datablock I

CCDC reference: 269417

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.054
  • wR factor = 0.166
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.10 Ratio
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.794 0.980 Tmin' and Tmax expected: 0.974 0.984 RR' = 0.818 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.37 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

3-[(2,6-Diisopropylphenyl)iminomethyl]-2-naphthol top
Crystal data top
C23H25NOF(000) = 712
Mr = 331.44Dx = 1.117 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.3365 (11) ÅCell parameters from 831 reflections
b = 22.824 (5) Åθ = 2.4–23.6°
c = 9.3508 (12) ŵ = 0.07 mm1
β = 98.629 (8)°T = 293 K
V = 1970.0 (6) Å3Prism, yellow
Z = 40.38 × 0.36 × 0.24 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4091 independent reflections
Radiation source: fine-focus sealed tube2096 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.794, Tmax = 0.980k = 2028
11528 measured reflectionsl = 811
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0715P)2 + 0.2668P]
where P = (Fo2 + 2Fc2)/3
4091 reflections(Δ/σ)max = 0.001
254 parametersΔρmax = 0.24 e Å3
31 restraintsΔρmin = 0.19 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*/UeqOcc. (<1)
O10.24346 (19)0.22292 (7)0.01498 (19)0.0802 (6)
H10.276 (3)0.2533 (8)0.030 (3)0.120*
N10.39709 (18)0.28728 (7)0.16248 (18)0.0493 (4)
C10.3076 (2)0.17714 (9)0.0568 (2)0.0546 (6)
C20.2663 (3)0.12114 (11)0.0029 (3)0.0719 (7)
H20.19490.11730.07730.086*
C30.3301 (3)0.07321 (10)0.0672 (3)0.0750 (8)
H30.30260.03660.02890.090*
C40.4375 (2)0.07639 (9)0.1911 (3)0.0590 (6)
C50.5029 (3)0.02583 (11)0.2579 (3)0.0856 (9)
H50.47700.01080.21860.103*
C60.6028 (3)0.02968 (12)0.3783 (4)0.0918 (9)
H60.64420.00420.42170.110*
C70.6434 (3)0.08403 (11)0.4372 (3)0.0831 (8)
H70.71210.08660.52000.100*
C80.5827 (2)0.13382 (9)0.3735 (3)0.0635 (6)
H80.61140.16990.41420.076*
C90.4784 (2)0.13224 (8)0.2487 (2)0.0457 (5)
C100.4129 (2)0.18358 (8)0.1783 (2)0.0425 (5)
C110.4542 (2)0.24162 (8)0.2284 (2)0.0437 (5)
H110.52360.24620.31000.052*
C120.4295 (2)0.34529 (8)0.2142 (2)0.0460 (5)
C130.3649 (2)0.36655 (9)0.3287 (2)0.0582 (6)
C170.3865 (3)0.42469 (10)0.3655 (3)0.0731 (7)
H170.34480.43990.44190.088*
C180.4676 (3)0.46064 (10)0.2924 (3)0.0757 (8)
H180.47920.49990.31850.091*
C190.5317 (3)0.43906 (9)0.1808 (3)0.0661 (7)
H190.58750.46380.13250.079*
C200.5148 (2)0.38086 (9)0.1387 (2)0.0521 (5)
C210.5897 (3)0.35577 (11)0.0190 (3)0.0743 (7)
H210.53970.31940.01460.089*
C220.7459 (4)0.34041 (15)0.0776 (4)0.1186 (12)
H22A0.79790.37540.10980.178*
H22B0.79040.32230.00260.178*
H22C0.74810.31380.15730.178*
C230.5847 (4)0.39645 (14)0.1103 (3)0.1169 (11)
H23A0.48590.40660.14550.175*
H23B0.62630.37710.18550.175*
H23C0.63880.43140.08170.175*
C140.2692 (3)0.32828 (12)0.4079 (3)0.0831 (8)
H14A0.30660.28920.40410.100*0.66 (3)
H14B0.26900.28950.36800.100*0.34 (3)
C150.2847 (15)0.3399 (7)0.5677 (8)0.142 (4)0.66 (3)
H15A0.38550.34380.60640.213*0.66 (3)
H15B0.24370.30790.61450.213*0.66 (3)
H15C0.23480.37550.58430.213*0.66 (3)
C160.1135 (6)0.3273 (6)0.3353 (12)0.120 (3)0.66 (3)
H16A0.10890.31260.23860.180*0.66 (3)
H16B0.07470.36630.33230.180*0.66 (3)
H16C0.05800.30240.38890.180*0.66 (3)
C15'0.330 (2)0.3220 (9)0.5662 (12)0.108 (6)0.34 (3)
H15D0.41960.30050.57560.162*0.34 (3)
H15E0.26230.30130.61500.162*0.34 (3)
H15F0.34780.36010.60860.162*0.34 (3)
C16'0.1186 (15)0.3552 (12)0.387 (3)0.125 (6)0.34 (3)
H16D0.12080.39140.43960.187*0.34 (3)
H16E0.05220.32860.42220.187*0.34 (3)
H16F0.08760.36250.28600.187*0.34 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0882 (12)0.0636 (11)0.0752 (13)0.0083 (9)0.0324 (10)0.0087 (9)
N10.0530 (10)0.0436 (10)0.0496 (11)0.0017 (8)0.0019 (8)0.0021 (8)
C10.0549 (13)0.0517 (13)0.0548 (14)0.0083 (10)0.0001 (11)0.0026 (10)
C20.0797 (17)0.0645 (15)0.0643 (16)0.0220 (13)0.0129 (13)0.0047 (12)
C30.090 (2)0.0516 (14)0.0799 (19)0.0219 (13)0.0020 (16)0.0132 (13)
C40.0617 (15)0.0470 (13)0.0692 (16)0.0062 (10)0.0124 (12)0.0006 (11)
C50.093 (2)0.0449 (15)0.118 (3)0.0010 (13)0.0107 (19)0.0029 (14)
C60.084 (2)0.0594 (17)0.127 (3)0.0154 (14)0.0010 (19)0.0235 (16)
C70.0718 (17)0.0703 (17)0.098 (2)0.0042 (13)0.0159 (15)0.0173 (15)
C80.0596 (14)0.0522 (14)0.0739 (17)0.0008 (10)0.0053 (12)0.0051 (11)
C90.0409 (11)0.0453 (12)0.0521 (13)0.0034 (8)0.0105 (10)0.0002 (9)
C100.0407 (11)0.0451 (11)0.0416 (12)0.0057 (8)0.0056 (9)0.0019 (9)
C110.0409 (11)0.0490 (12)0.0410 (11)0.0005 (9)0.0051 (9)0.0012 (9)
C120.0477 (12)0.0407 (11)0.0471 (13)0.0038 (9)0.0004 (10)0.0018 (9)
C130.0579 (14)0.0563 (14)0.0612 (15)0.0096 (10)0.0116 (11)0.0006 (11)
C170.0860 (18)0.0601 (16)0.0742 (18)0.0193 (13)0.0150 (15)0.0089 (13)
C180.097 (2)0.0415 (13)0.083 (2)0.0097 (13)0.0055 (16)0.0064 (13)
C190.0768 (17)0.0475 (13)0.0711 (17)0.0085 (11)0.0012 (14)0.0080 (12)
C200.0568 (13)0.0474 (12)0.0504 (13)0.0003 (10)0.0026 (11)0.0037 (10)
C210.0881 (19)0.0702 (15)0.0696 (18)0.0141 (14)0.0281 (15)0.0019 (13)
C220.107 (3)0.136 (3)0.123 (3)0.043 (2)0.048 (2)0.010 (2)
C230.148 (3)0.133 (3)0.075 (2)0.004 (2)0.034 (2)0.020 (2)
C140.086 (2)0.0903 (19)0.081 (2)0.0043 (15)0.0377 (17)0.0018 (15)
C150.152 (7)0.181 (8)0.108 (5)0.016 (6)0.063 (4)0.005 (5)
C160.075 (4)0.143 (7)0.146 (6)0.023 (3)0.025 (4)0.001 (5)
C15'0.127 (9)0.114 (9)0.087 (8)0.000 (7)0.026 (6)0.041 (6)
C16'0.103 (8)0.150 (10)0.129 (10)0.011 (7)0.048 (7)0.021 (7)
Geometric parameters (Å, º) top
O1—C11.334 (3)C19—C201.388 (3)
O1—H10.846 (10)C19—H190.9300
N1—C111.285 (2)C20—C211.518 (3)
N1—C121.426 (2)C21—C231.520 (4)
C1—C101.394 (3)C21—C221.520 (4)
C1—C21.406 (3)C21—H210.9800
C2—C31.343 (3)C22—H22A0.9600
C2—H20.9300C22—H22B0.9600
C3—C41.416 (3)C22—H22C0.9600
C3—H30.9300C23—H23A0.9600
C4—C51.407 (3)C23—H23B0.9600
C4—C91.414 (3)C23—H23C0.9600
C5—C61.353 (4)C14—C151.503 (7)
C5—H50.9300C14—C161.509 (6)
C6—C71.387 (4)C14—C15'1.511 (8)
C6—H60.9300C14—C16'1.520 (8)
C7—C81.366 (3)C14—H14A0.9599
C7—H70.9300C14—H14B0.9599
C8—C91.403 (3)C15—H15A0.9600
C8—H80.9300C15—H15B0.9600
C9—C101.435 (3)C15—H15C0.9600
C10—C111.438 (2)C16—H16A0.9600
C11—H110.9300C16—H16B0.9600
C12—C131.393 (3)C16—H16C0.9600
C12—C201.400 (3)C15'—H15D0.9600
C13—C171.378 (3)C15'—H15E0.9600
C13—C141.519 (3)C15'—H15F0.9600
C17—C181.367 (3)C16'—H16D0.9600
C17—H170.9300C16'—H16E0.9600
C18—C191.371 (3)C16'—H16F0.9600
C18—H180.9300
C1—O1—H1107 (2)C19—C20—C21121.6 (2)
C11—N1—C12122.58 (17)C12—C20—C21120.84 (18)
O1—C1—C10122.40 (18)C20—C21—C23113.2 (2)
O1—C1—C2117.0 (2)C20—C21—C22110.2 (2)
C10—C1—C2120.6 (2)C23—C21—C22109.9 (3)
C3—C2—C1120.0 (2)C20—C21—H21107.8
C3—C2—H2120.0C23—C21—H21107.8
C1—C2—H2120.0C22—C21—H21107.8
C2—C3—C4122.4 (2)C21—C22—H22A109.5
C2—C3—H3118.8C21—C22—H22B109.5
C4—C3—H3118.8H22A—C22—H22B109.5
C5—C4—C9119.7 (2)C21—C22—H22C109.5
C5—C4—C3121.9 (2)H22A—C22—H22C109.5
C9—C4—C3118.4 (2)H22B—C22—H22C109.5
C6—C5—C4121.0 (2)C21—C23—H23A109.5
C6—C5—H5119.5C21—C23—H23B109.5
C4—C5—H5119.5H23A—C23—H23B109.5
C5—C6—C7120.1 (2)C21—C23—H23C109.5
C5—C6—H6119.9H23A—C23—H23C109.5
C7—C6—H6119.9H23B—C23—H23C109.5
C8—C7—C6120.0 (3)C15—C14—C16113.1 (5)
C8—C7—H7120.0C15—C14—C13114.0 (5)
C6—C7—H7120.0C16—C14—C13112.7 (4)
C7—C8—C9122.1 (2)C15'—C14—C13111.7 (8)
C7—C8—H8118.9C15'—C14—C16'111.7 (7)
C9—C8—H8118.9C13—C14—C16'107.8 (7)
C8—C9—C4117.00 (19)C15—C14—H14A102.7
C8—C9—C10123.73 (18)C16—C14—H14A107.5
C4—C9—C10119.27 (19)C13—C14—H14A105.8
C1—C10—C9119.20 (17)C15'—C14—H14B105.8
C1—C10—C11118.96 (17)C13—C14—H14B107.9
C9—C10—C11121.84 (18)C16'—C14—H14B112.0
N1—C11—C10121.27 (19)C14—C15—H15A109.5
N1—C11—H11119.4C14—C15—H15B109.5
C10—C11—H11119.4C14—C15—H15C109.5
C13—C12—C20122.04 (18)C14—C16—H16A109.5
C13—C12—N1119.28 (18)C14—C16—H16B109.5
C20—C12—N1118.39 (18)C14—C16—H16C109.5
C17—C13—C12117.6 (2)C14—C15'—H15D109.5
C17—C13—C14120.5 (2)C14—C15'—H15E109.5
C12—C13—C14121.9 (2)H15D—C15'—H15E109.5
C18—C17—C13121.7 (2)C14—C15'—H15F109.5
C18—C17—H17119.2H15D—C15'—H15F109.5
C13—C17—H17119.2H15E—C15'—H15F109.5
C17—C18—C19120.2 (2)C14—C16'—H16D109.5
C17—C18—H18119.9C14—C16'—H16E109.5
C19—C18—H18119.9H16D—C16'—H16E109.5
C18—C19—C20121.0 (2)C14—C16'—H16F109.5
C18—C19—H19119.5H16D—C16'—H16F109.5
C20—C19—H19119.5H16E—C16'—H16F109.5
C19—C20—C12117.5 (2)
O1—C1—C2—C3177.9 (2)C11—N1—C12—C20108.1 (2)
C10—C1—C2—C31.1 (4)C20—C12—C13—C170.6 (3)
C1—C2—C3—C41.2 (4)N1—C12—C13—C17173.18 (19)
C2—C3—C4—C5179.7 (2)C20—C12—C13—C14178.4 (2)
C2—C3—C4—C90.1 (4)N1—C12—C13—C144.6 (3)
C9—C4—C5—C61.2 (4)C12—C13—C17—C180.3 (4)
C3—C4—C5—C6178.4 (3)C14—C13—C17—C18177.5 (2)
C4—C5—C6—C70.7 (5)C13—C17—C18—C191.0 (4)
C5—C6—C7—C80.0 (5)C17—C18—C19—C200.7 (4)
C6—C7—C8—C90.2 (4)C18—C19—C20—C120.2 (3)
C7—C8—C9—C40.4 (3)C18—C19—C20—C21177.7 (2)
C7—C8—C9—C10179.6 (2)C13—C12—C20—C190.8 (3)
C5—C4—C9—C81.1 (3)N1—C12—C20—C19173.00 (18)
C3—C4—C9—C8178.6 (2)C13—C12—C20—C21177.1 (2)
C5—C4—C9—C10178.9 (2)N1—C12—C20—C219.1 (3)
C3—C4—C9—C101.5 (3)C19—C20—C21—C2342.5 (3)
O1—C1—C10—C9179.20 (19)C12—C20—C21—C23139.7 (2)
C2—C1—C10—C90.3 (3)C19—C20—C21—C2281.0 (3)
O1—C1—C10—C110.1 (3)C12—C20—C21—C2296.8 (3)
C2—C1—C10—C11178.8 (2)C17—C13—C14—C1538.9 (8)
C8—C9—C10—C1178.4 (2)C12—C13—C14—C15143.4 (8)
C4—C9—C10—C11.6 (3)C17—C13—C14—C1691.9 (8)
C8—C9—C10—C112.5 (3)C12—C13—C14—C1685.9 (8)
C4—C9—C10—C11177.49 (18)C17—C13—C14—C15'63.4 (10)
C12—N1—C11—C10176.27 (18)C12—C13—C14—C15'118.9 (10)
C1—C10—C11—N10.7 (3)C17—C13—C14—C16'59.7 (14)
C9—C10—C11—N1178.40 (18)C12—C13—C14—C16'118.0 (14)
C11—N1—C12—C1378.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.85 (1)1.73 (2)2.501 (2)151 (3)
 

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