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The title Schiff base compound, C28H26N2O2, possesses both OH and NH tautomeric character in its mol­ecular structure. While the OH side of the compound is described as an inter­mediate state, its NH side adopts a predominantly zwitterionic form. The mol­ecular structure of the compound is stabilized by both N+—H...O and O—H...N intra­molecular hydrogen bonds. There are two weak C—H...O hydrogen bonds leading to polymeric chains of topology C(5) and C(13) running along the b axis of the unit cell. In addition, inter­molecular C—H...π inter­actions serve to stabilize the extended structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107005689/fa3062sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107005689/fa3062Isup2.hkl
Contains datablock I

tif

Tagged Image Format File (TIF) image https://doi.org/10.1107/S0108270107005689/fa3062sup3.tif
Supplementary material

tif

Tagged Image Format File (TIF) image https://doi.org/10.1107/S0108270107005689/fa3062sup4.tif
Supplementary material

CCDC reference: 645569

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).

1-((E)-{(1R,2R)-2-[(E)-(2-Hydroxy-1- naphthyl)methyleneamino]cyclohexyl}iminiomethyl)naphthalen-2-olate top
Crystal data top
C28H26N2O2F(000) = 896
Mr = 422.51Dx = 1.223 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2 abCell parameters from 29494 reflections
a = 9.4829 (4) Åθ = 1.6–27.2°
b = 9.5307 (4) ŵ = 0.08 mm1
c = 25.3955 (8) ÅT = 296 K
V = 2295.21 (15) Å3Prismatic plate, yellow
Z = 40.58 × 0.54 × 0.42 mm
Data collection top
Stoe IPDS II
diffractometer
2922 independent reflections
Radiation source: fine-focus sealed tube2186 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.089
Detector resolution: 6.67 pixels mm-1θmax = 27.2°, θmin = 1.6°
ω scansh = 1212
Absorption correction: integration
(X-AREA; Stoe & Cie, 2002)
k = 1212
Tmin = 0.954, Tmax = 0.967l = 3232
37222 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0589P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.082(Δ/σ)max = 0.001
S = 0.92Δρmax = 0.15 e Å3
2922 reflectionsΔρmin = 0.12 e Å3
355 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
66 restraintsExtinction coefficient: 0.019 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: known absolute configuration of starting material
Secondary atom site location: difference Fourier map
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
C10.60950 (17)0.24858 (19)0.66126 (6)0.0689 (4)
H1A0.56660.17110.64160.083*
C20.75698 (19)0.2044 (2)0.67752 (9)0.0877 (5)
H2A0.79910.27780.69880.105*
H2B0.75130.12020.69890.105*
C30.8499 (2)0.1762 (3)0.63014 (10)0.1014 (7)
H3A0.94420.15250.64190.122*
H3B0.81280.09680.61060.122*
C40.8563 (2)0.3026 (2)0.59464 (10)0.0954 (6)
H4A0.91000.27960.56330.114*
H4B0.90450.37830.61270.114*
C50.7108 (2)0.3507 (2)0.57882 (8)0.0870 (5)
H5A0.66870.28010.55620.104*
H5B0.71910.43660.55860.104*
C60.61296 (18)0.37695 (19)0.62574 (7)0.0701 (4)
H60.64670.45820.64580.084*
C70.42520 (18)0.53221 (19)0.60198 (6)0.0659 (4)
C80.29757 (17)0.56628 (18)0.57405 (6)0.0638 (4)
C90.2259 (2)0.4591 (2)0.54718 (7)0.0753 (4)
C100.1069 (2)0.4942 (3)0.51527 (8)0.0869 (6)
C110.0633 (2)0.6273 (3)0.51089 (8)0.0889 (6)
C120.13112 (19)0.7395 (2)0.53717 (7)0.0733 (4)
C130.0838 (2)0.8795 (3)0.53194 (9)0.0889 (6)
C140.1485 (3)0.9863 (2)0.55696 (8)0.0913 (6)
C150.2616 (3)0.9568 (2)0.58986 (8)0.0852 (5)
C160.3095 (2)0.8226 (2)0.59711 (7)0.0735 (4)
C170.24853 (17)0.70844 (18)0.56997 (6)0.0634 (4)
C180.41053 (16)0.20335 (18)0.71872 (6)0.0640 (4)
C190.33074 (16)0.22021 (17)0.76514 (6)0.0628 (4)
C200.37906 (18)0.31459 (18)0.80435 (7)0.0698 (4)
C210.3015 (2)0.3235 (2)0.85245 (8)0.0814 (5)
C220.1813 (2)0.2515 (2)0.85941 (8)0.0852 (5)
C230.12500 (18)0.1608 (2)0.82012 (7)0.0758 (4)
C240.0038 (2)0.0905 (3)0.82695 (11)0.0972 (7)
C250.0563 (3)0.0028 (3)0.79015 (12)0.1054 (7)
C260.0186 (3)0.0185 (3)0.74428 (11)0.0997 (7)
C270.1447 (2)0.0483 (2)0.73585 (9)0.0831 (5)
C280.20119 (16)0.14157 (18)0.77278 (7)0.0666 (4)
N10.47146 (15)0.40571 (17)0.60523 (6)0.0738 (4)
N20.52373 (15)0.27492 (16)0.70789 (6)0.0692 (4)
O10.26563 (18)0.32743 (15)0.54900 (7)0.0992 (4)
O20.49034 (14)0.39085 (16)0.79822 (5)0.0872 (4)
H20.545 (3)0.346 (3)0.7394 (11)0.125 (9)*
H260.012 (3)0.088 (3)0.7209 (12)0.136 (10)*
H250.147 (3)0.043 (3)0.7967 (10)0.132 (9)*
H240.053 (3)0.109 (3)0.8588 (9)0.109 (7)*
H210.334 (2)0.387 (3)0.8784 (9)0.097 (6)*
H270.194 (2)0.029 (2)0.7027 (8)0.087 (6)*
H220.131 (3)0.252 (3)0.8935 (10)0.113 (7)*
H180.3819 (18)0.131 (2)0.6943 (7)0.071 (5)*
H70.480 (2)0.612 (2)0.6175 (7)0.076 (5)*
H140.119 (2)1.091 (3)0.5517 (9)0.109 (7)*
H150.306 (3)1.037 (3)0.6091 (9)0.110 (7)*
H160.390 (2)0.799 (2)0.6210 (8)0.082 (5)*
H110.022 (3)0.649 (3)0.4892 (11)0.136 (9)*
H130.002 (3)0.891 (3)0.5086 (10)0.110 (7)*
H100.058 (2)0.419 (2)0.4982 (9)0.102 (7)*
H10.368 (5)0.324 (4)0.5699 (14)0.195 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0669 (8)0.0748 (10)0.0651 (9)0.0009 (8)0.0057 (7)0.0017 (8)
C20.0721 (10)0.0982 (13)0.0927 (12)0.0098 (10)0.0032 (9)0.0176 (11)
C30.0802 (11)0.1042 (15)0.1198 (17)0.0150 (12)0.0246 (12)0.0188 (13)
C40.0802 (11)0.1005 (15)0.1055 (15)0.0035 (11)0.0256 (11)0.0066 (12)
C50.0896 (12)0.0947 (13)0.0767 (11)0.0022 (11)0.0137 (10)0.0112 (10)
C60.0676 (9)0.0735 (10)0.0691 (9)0.0034 (8)0.0013 (8)0.0041 (8)
C70.0661 (9)0.0735 (10)0.0580 (8)0.0056 (8)0.0020 (7)0.0028 (7)
C80.0641 (8)0.0731 (10)0.0541 (8)0.0093 (8)0.0016 (7)0.0001 (7)
C90.0799 (11)0.0751 (11)0.0711 (10)0.0124 (9)0.0043 (9)0.0011 (8)
C100.0862 (12)0.0948 (14)0.0796 (12)0.0191 (12)0.0177 (10)0.0014 (10)
C110.0873 (12)0.1028 (15)0.0766 (11)0.0077 (11)0.0185 (10)0.0096 (11)
C120.0745 (10)0.0866 (11)0.0587 (9)0.0013 (9)0.0029 (8)0.0073 (8)
C130.0906 (13)0.0997 (15)0.0763 (11)0.0120 (12)0.0002 (11)0.0177 (11)
C140.1094 (15)0.0829 (13)0.0816 (12)0.0113 (12)0.0096 (12)0.0047 (11)
C150.0984 (14)0.0811 (12)0.0761 (11)0.0008 (11)0.0108 (11)0.0108 (10)
C160.0751 (10)0.0818 (11)0.0637 (9)0.0014 (9)0.0044 (9)0.0079 (9)
C170.0634 (8)0.0763 (10)0.0505 (7)0.0058 (8)0.0078 (6)0.0023 (7)
C180.0617 (8)0.0689 (9)0.0613 (8)0.0018 (7)0.0039 (7)0.0049 (7)
C190.0621 (8)0.0682 (9)0.0583 (8)0.0046 (7)0.0015 (6)0.0034 (7)
C200.0710 (9)0.0705 (10)0.0679 (9)0.0070 (8)0.0041 (8)0.0012 (8)
C210.0915 (13)0.0842 (12)0.0686 (10)0.0124 (11)0.0005 (10)0.0105 (9)
C220.0901 (13)0.0916 (13)0.0738 (12)0.0169 (11)0.0168 (10)0.0030 (10)
C230.0703 (9)0.0780 (10)0.0790 (11)0.0118 (9)0.0114 (9)0.0079 (9)
C240.0766 (12)0.1065 (16)0.1083 (16)0.0043 (12)0.0269 (12)0.0135 (14)
C250.0732 (12)0.1169 (18)0.1261 (19)0.0170 (12)0.0109 (13)0.0155 (16)
C260.0830 (14)0.1065 (16)0.1098 (16)0.0214 (13)0.0078 (13)0.0000 (14)
C270.0764 (11)0.0942 (13)0.0786 (12)0.0122 (10)0.0000 (10)0.0001 (10)
C280.0628 (8)0.0696 (9)0.0673 (9)0.0049 (7)0.0013 (8)0.0065 (8)
N10.0716 (8)0.0776 (9)0.0722 (9)0.0023 (8)0.0060 (7)0.0046 (7)
N20.0671 (7)0.0775 (8)0.0632 (8)0.0028 (7)0.0025 (6)0.0022 (7)
O10.1094 (10)0.0726 (8)0.1156 (11)0.0112 (8)0.0249 (10)0.0044 (7)
O20.0860 (8)0.0937 (9)0.0819 (8)0.0166 (7)0.0046 (7)0.0105 (7)
Geometric parameters (Å, º) top
C1—N21.458 (2)C13—C141.347 (3)
C1—C21.518 (3)C13—H130.98 (3)
C1—C61.520 (2)C14—C151.388 (3)
C1—H1A0.9800C14—H141.05 (2)
C2—C31.515 (3)C15—C161.370 (3)
C2—H2A0.9700C15—H151.00 (3)
C2—H2B0.9700C16—C171.412 (2)
C3—C41.506 (3)C16—H161.00 (2)
C3—H3A0.9700C18—N21.301 (2)
C3—H3B0.9700C18—C191.410 (2)
C4—C51.508 (3)C18—H180.968 (19)
C4—H4A0.9700C19—C201.418 (2)
C4—H4B0.9700C19—C281.452 (2)
C5—C61.531 (3)C20—O21.291 (2)
C5—H5A0.9700C20—C211.428 (2)
C5—H5B0.9700C21—C221.342 (3)
C6—N11.465 (2)C21—H210.95 (2)
C6—H60.9800C22—C231.424 (3)
C7—N11.286 (2)C22—H220.99 (2)
C7—C81.440 (2)C23—C241.404 (3)
C7—H71.01 (2)C23—C281.415 (2)
C8—C91.404 (2)C24—C251.349 (4)
C8—C171.436 (2)C24—H240.95 (2)
C9—O11.311 (2)C25—C261.379 (4)
C9—C101.429 (3)C25—H250.98 (3)
C10—C111.338 (3)C26—C271.372 (3)
C10—H100.96 (2)C26—H260.94 (3)
C11—C121.416 (3)C27—C281.399 (3)
C11—H111.00 (3)C27—H270.98 (2)
C12—C131.414 (3)N2—H21.07 (3)
C12—C171.422 (2)O1—H11.11 (4)
N2—C1—C2109.93 (14)C14—C13—C12121.6 (2)
N2—C1—C6110.81 (14)C14—C13—H13124.3 (16)
C2—C1—C6111.40 (14)C12—C13—H13114.1 (16)
N2—C1—H1A108.2C13—C14—C15118.9 (2)
C2—C1—H1A108.2C13—C14—H14122.8 (13)
C6—C1—H1A108.2C15—C14—H14118.2 (13)
C3—C2—C1111.65 (17)C16—C15—C14121.7 (2)
C3—C2—H2A109.3C16—C15—H15120.7 (14)
C1—C2—H2A109.3C14—C15—H15117.5 (14)
C3—C2—H2B109.3C15—C16—C17121.22 (19)
C1—C2—H2B109.3C15—C16—H16123.0 (12)
H2A—C2—H2B108.0C17—C16—H16115.8 (12)
C4—C3—C2110.90 (18)C16—C17—C12116.50 (17)
C4—C3—H3A109.5C16—C17—C8124.00 (15)
C2—C3—H3A109.5C12—C17—C8119.51 (15)
C4—C3—H3B109.5N2—C18—C19124.03 (16)
C2—C3—H3B109.5N2—C18—H18118.1 (10)
H3A—C3—H3B108.0C19—C18—H18117.8 (10)
C3—C4—C5111.46 (18)C18—C19—C20119.08 (15)
C3—C4—H4A109.3C18—C19—C28120.46 (15)
C5—C4—H4A109.3C20—C19—C28120.46 (14)
C3—C4—H4B109.3O2—C20—C19122.46 (15)
C5—C4—H4B109.3O2—C20—C21119.39 (17)
H4A—C4—H4B108.0C19—C20—C21118.15 (16)
C4—C5—C6113.39 (17)C22—C21—C20121.31 (19)
C4—C5—H5A108.9C22—C21—H21120.8 (14)
C6—C5—H5A108.9C20—C21—H21117.7 (14)
C4—C5—H5B108.9C21—C22—C23122.45 (18)
C6—C5—H5B108.9C21—C22—H22121.5 (15)
H5A—C5—H5B107.7C23—C22—H22115.8 (15)
N1—C6—C1109.98 (14)C24—C23—C28119.2 (2)
N1—C6—C5108.01 (14)C24—C23—C22121.96 (19)
C1—C6—C5110.07 (15)C28—C23—C22118.86 (17)
N1—C6—H6109.6C25—C24—C23122.1 (2)
C1—C6—H6109.6C25—C24—H24121.4 (15)
C5—C6—H6109.6C23—C24—H24116.5 (15)
N1—C7—C8121.99 (16)C24—C25—C26119.1 (2)
N1—C7—H7120.7 (11)C24—C25—H25118.9 (16)
C8—C7—H7117.2 (11)C26—C25—H25122.0 (16)
C9—C8—C17119.63 (15)C27—C26—C25120.8 (3)
C9—C8—C7118.85 (16)C27—C26—H26120.2 (18)
C17—C8—C7121.36 (15)C25—C26—H26118.5 (18)
O1—C9—C8122.68 (17)C26—C27—C28121.6 (2)
O1—C9—C10118.10 (18)C26—C27—H27117.6 (12)
C8—C9—C10119.19 (18)C28—C27—H27120.8 (12)
C11—C10—C9120.9 (2)C27—C28—C23117.17 (16)
C11—C10—H10121.6 (13)C27—C28—C19124.22 (16)
C9—C10—H10117.5 (13)C23—C28—C19118.60 (15)
C10—C11—C12122.5 (2)C7—N1—C6120.71 (16)
C10—C11—H11119.5 (18)C18—N2—C1122.78 (16)
C12—C11—H11118.0 (18)C18—N2—H2109.3 (13)
C13—C12—C11121.67 (19)C1—N2—H2127.7 (13)
C13—C12—C17120.01 (18)C9—O1—H1107 (2)
C11—C12—C17118.32 (18)
N2—C1—C2—C3179.89 (17)C9—C8—C17—C122.4 (2)
C6—C1—C2—C356.7 (2)C7—C8—C17—C12172.94 (14)
C1—C2—C3—C456.5 (3)N2—C18—C19—C203.8 (2)
C2—C3—C4—C554.5 (3)N2—C18—C19—C28176.51 (14)
C3—C4—C5—C653.8 (3)C18—C19—C20—O23.2 (2)
N2—C1—C6—N164.68 (18)C28—C19—C20—O2177.02 (15)
C2—C1—C6—N1172.60 (16)C18—C19—C20—C21176.11 (15)
N2—C1—C6—C5176.43 (15)C28—C19—C20—C213.6 (2)
C2—C1—C6—C553.7 (2)O2—C20—C21—C22176.56 (18)
C4—C5—C6—N1173.06 (18)C19—C20—C21—C224.1 (3)
C4—C5—C6—C153.0 (2)C20—C21—C22—C231.0 (3)
N1—C7—C8—C93.6 (2)C21—C22—C23—C24177.3 (2)
N1—C7—C8—C17178.88 (16)C21—C22—C23—C282.5 (3)
C17—C8—C9—O1179.60 (18)C28—C23—C24—C251.3 (3)
C7—C8—C9—O14.2 (3)C22—C23—C24—C25178.9 (2)
C17—C8—C9—C101.3 (2)C23—C24—C25—C260.1 (4)
C7—C8—C9—C10174.09 (16)C24—C25—C26—C270.1 (4)
O1—C9—C10—C11178.5 (2)C25—C26—C27—C280.9 (3)
C8—C9—C10—C110.1 (3)C26—C27—C28—C232.0 (3)
C9—C10—C11—C120.1 (3)C26—C27—C28—C19177.11 (19)
C10—C11—C12—C13179.8 (2)C24—C23—C28—C272.2 (3)
C10—C11—C12—C171.0 (3)C22—C23—C28—C27178.04 (17)
C11—C12—C13—C14180.0 (2)C24—C23—C28—C19177.00 (17)
C17—C12—C13—C140.8 (3)C22—C23—C28—C192.8 (2)
C12—C13—C14—C152.0 (3)C18—C19—C28—C271.4 (2)
C13—C14—C15—C160.5 (3)C20—C19—C28—C27178.85 (17)
C14—C15—C16—C172.1 (3)C18—C19—C28—C23179.49 (15)
C15—C16—C17—C123.1 (2)C20—C19—C28—C230.2 (2)
C15—C16—C17—C8177.22 (17)C8—C7—N1—C6169.28 (14)
C13—C12—C17—C161.7 (2)C1—C6—N1—C7139.10 (16)
C11—C12—C17—C16177.53 (17)C5—C6—N1—C7100.8 (2)
C13—C12—C17—C8178.61 (17)C19—C18—N2—C1175.69 (15)
C11—C12—C17—C82.1 (2)C2—C1—N2—C18118.12 (18)
C9—C8—C17—C16177.30 (16)C6—C1—N2—C18118.30 (17)
C7—C8—C17—C167.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N11.11 (4)1.54 (4)2.531 (2)146 (3)
N2+—H2···O2-1.07 (3)1.64 (3)2.566 (2)142 (2)
Geometric details of the intermolecular C—H···π interaction and weak C—H···O hydrogen bonds for (I) (Å,°) top
D—H···AD—HH···AD···AD—H···A
C16-H16···O2-i1.00 (2)2.50 (2)3.330 (2)140 (2)
C18-H18···O2-ii0.97 (2)2.60 (2)3.153 (2)117 (1)
C24-H24···Cg1iii0.95 (2)2.78 (2)3.711 (3)167 (2)
Symmetry codes: (i) 1-x, 1/2+y, 3/2-z; (ii) 1-x, -1/2+y, 3/2-z; (iii) -x, -1/2+y, 3/2-z.
 

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