organic compounds
E)-1(anthracen-9-ylmethylidene)[2-(morpholin-4-yl)ethyl]amine
of (aİlke Education and Health Foundation, Cappadocia Vocational College, The Medical Imaging Techniques Program, 50420 Mustafapaşa, Ürgüp, Nevşehir, Turkey, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
The title compound, C21H22N2O, crystallizes with two independent molecules in the In both molecules, the anthracene ring systems are almost planar, with maximum deviations of 0.071 (8) and 0.028 (7) Å, and make dihedral angles of 73.4 (2) and 73.3 (2)° with the least-squares planes formed by the four C atoms of the morpholine rings, which adopt a chair conformation. An intramolecular C—H⋯π interaction occurs. In the crystal, the packing is stabilized by weak C—H⋯O hydrogen bonds, which connect pairs of molecules into parallel to the c axis, and C—H⋯π interactions.
Keywords: crystal structure; C—H⋯π interactions; Schiff bases; anthracene; morpholine; methanimine.
CCDC reference: 1020122
1. Related literature
For background to the importance of ); Witkop & Ramachandran (1964); Solomon & Lowery (1993); Gerdemann et al. (2002).
and their uses, see: Dhar & Taploo (19822. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 1020122
10.1107/S1600536814018807/xu5815sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018807/xu5815Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018807/xu5815Isup3.cml
Reaction of anthracene-9-carbaldehyde (1.00 mmol) with 2-morpholinoethanamine (1.00 mmol) in refluxing ethanol gave the title compound (I). Recrystallization from ethanol gave yellow crystals in 85% yield. Mp: 381–383 K. IR (KBr) cm-1:1643 (C=N). 1H-NMR (250 MHz, CDCl3), δ (p.p.m.): 2.58 (CH2—N morpholine, t, 4H, J=5 Hz), 2.84 (morpholine-CH2—CH2, t, 2H, J=7.5 Hz), 3.73 (CH2—O morpholine, t, 4H, J=5 Hz), 4.00 (morpholine-CH2—CH2, t, 2H, J=5 Hz), 7.37–7.94 (aromatic H, m, 9H), 8.45 (HC=N, s, 1H). 13CNMR (62.9 MHz, CDCl3), δ (p.p.m): 53.9 (CH2—N morpholine), 58.9 and 59.6 (N—CH2—CH2—N), 67.0 (CH2—O morpholin), 124.9–131.2 (aromatic carbons), 161.4 (C=N).
H atoms were located geometrically with C—H = 0.93 and 0.97 Å, and refined using a riding model with Uiso(H) = 1.2Ueq(C) for the aromatic and methylene H atoms. The crystal quality and data was not good enough so a sufficient fraction of the unique data is above the 2 sigma level. A total of 749 estimated Friedel pairs were merged before
and not used as independent data. The was found to be meaningless and was omitted.Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).Fig. 1. View of the two molecules (A, B) of the title compound in the asymmetric unit with the atom-labelling scheme and 30% probability displacement ellipsoids. | |
Fig. 2. Packing diagram of the title compound viewed down the a axis. Hydrogen bonds are indicated by broken lines. H atoms not participating in hydrogen bonding have been omitted for clarity. |
C21H22N2O | F(000) = 680 |
Mr = 318.41 | Dx = 1.181 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 10759 reflections |
a = 6.0451 (3) Å | θ = 1.7–27.1° |
b = 17.8151 (10) Å | µ = 0.07 mm−1 |
c = 16.8627 (8) Å | T = 296 K |
β = 99.690 (4)° | Needle, yellow |
V = 1790.10 (16) Å3 | 0.43 × 0.23 × 0.12 mm |
Z = 4 |
Stoe IPDS 2 diffractometer | 7325 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2245 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.116 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.5°, θmin = 1.7° |
ω scans | h = −7→7 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −22→22 |
Tmin = 0.980, Tmax = 0.993 | l = −21→21 |
22689 measured reflections |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0001P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.71 | (Δ/σ)max = 0.001 |
7325 reflections | Δρmax = 0.12 e Å−3 |
433 parameters | Δρmin = −0.10 e Å−3 |
C21H22N2O | V = 1790.10 (16) Å3 |
Mr = 318.41 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.0451 (3) Å | µ = 0.07 mm−1 |
b = 17.8151 (10) Å | T = 296 K |
c = 16.8627 (8) Å | 0.43 × 0.23 × 0.12 mm |
β = 99.690 (4)° |
Stoe IPDS 2 diffractometer | 7325 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2245 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.993 | Rint = 0.116 |
22689 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 1 restraint |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 0.71 | Δρmax = 0.12 e Å−3 |
7325 reflections | Δρmin = −0.10 e Å−3 |
433 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.5030 (14) | 1.1304 (3) | 0.8402 (4) | 0.151 (3) | |
N1 | 0.6844 (9) | 1.0984 (3) | 0.6979 (4) | 0.091 (3) | |
N2 | 0.9321 (9) | 1.0010 (3) | 0.5933 (3) | 0.083 (2) | |
C1 | 0.4497 (12) | 1.0827 (4) | 0.7044 (5) | 0.125 (4) | |
C2 | 0.4292 (17) | 1.0681 (5) | 0.7902 (6) | 0.165 (5) | |
C3 | 0.7314 (19) | 1.1459 (5) | 0.8339 (6) | 0.155 (6) | |
C4 | 0.7548 (14) | 1.1610 (3) | 0.7501 (6) | 0.121 (4) | |
C5 | 0.7151 (11) | 1.1119 (3) | 0.6140 (4) | 0.102 (3) | |
C6 | 0.7207 (12) | 1.0390 (4) | 0.5671 (4) | 0.103 (3) | |
C7 | 0.9286 (11) | 0.9462 (4) | 0.6392 (4) | 0.083 (3) | |
C8 | 1.1260 (11) | 0.9000 (3) | 0.6682 (5) | 0.075 (3) | |
C9 | 1.2703 (12) | 0.8691 (3) | 0.6193 (4) | 0.069 (3) | |
C10 | 1.2220 (11) | 0.8797 (3) | 0.5362 (5) | 0.095 (3) | |
C11 | 1.3547 (14) | 0.8477 (4) | 0.4871 (4) | 0.103 (3) | |
C12 | 1.5368 (14) | 0.8018 (4) | 0.5200 (5) | 0.112 (4) | |
C13 | 1.5893 (12) | 0.7909 (3) | 0.5997 (5) | 0.094 (3) | |
C14 | 1.4558 (13) | 0.8241 (3) | 0.6516 (5) | 0.079 (3) | |
C15 | 1.4988 (12) | 0.8134 (4) | 0.7345 (5) | 0.089 (3) | |
C16 | 1.3580 (16) | 0.8435 (4) | 0.7827 (4) | 0.089 (4) | |
C17 | 1.4078 (14) | 0.8284 (4) | 0.8665 (6) | 0.119 (4) | |
C18 | 1.2768 (16) | 0.8546 (5) | 0.9180 (5) | 0.131 (5) | |
C19 | 1.0911 (18) | 0.8962 (5) | 0.8894 (6) | 0.120 (4) | |
C20 | 1.0344 (12) | 0.9135 (4) | 0.8089 (5) | 0.097 (4) | |
C21 | 1.1684 (13) | 0.8875 (4) | 0.7520 (5) | 0.082 (3) | |
O2 | −0.0218 (13) | 0.3492 (4) | 0.9153 (4) | 0.143 (3) | |
N3 | 0.1892 (9) | 0.3720 (2) | 0.7801 (3) | 0.075 (2) | |
N4 | 0.4442 (8) | 0.4611 (3) | 0.6707 (3) | 0.086 (2) | |
C22 | 0.2622 (11) | 0.3138 (3) | 0.8388 (5) | 0.104 (3) | |
C23 | 0.2071 (17) | 0.3359 (5) | 0.9198 (5) | 0.147 (5) | |
C24 | −0.0968 (13) | 0.4068 (4) | 0.8585 (5) | 0.122 (4) | |
C25 | −0.0489 (11) | 0.3848 (3) | 0.7777 (4) | 0.094 (3) | |
C26 | 0.2383 (11) | 0.3506 (3) | 0.6997 (5) | 0.096 (3) | |
C27 | 0.2407 (11) | 0.4180 (3) | 0.6453 (4) | 0.091 (3) | |
C28 | 0.4249 (10) | 0.5193 (3) | 0.7114 (4) | 0.078 (3) | |
C29 | 0.6164 (11) | 0.5675 (3) | 0.7442 (4) | 0.071 (3) | |
C30 | 0.6443 (13) | 0.5896 (3) | 0.8261 (4) | 0.075 (3) | |
C31 | 0.4994 (12) | 0.5602 (4) | 0.8772 (5) | 0.105 (4) | |
C32 | 0.5272 (15) | 0.5804 (5) | 0.9561 (5) | 0.122 (4) | |
C33 | 0.7021 (18) | 0.6295 (4) | 0.9876 (5) | 0.123 (4) | |
C34 | 0.8488 (14) | 0.6564 (4) | 0.9425 (5) | 0.110 (4) | |
C35 | 0.8258 (13) | 0.6379 (3) | 0.8593 (5) | 0.079 (3) | |
C36 | 0.9658 (13) | 0.6628 (3) | 0.8079 (5) | 0.087 (3) | |
C37 | 0.9342 (13) | 0.6426 (4) | 0.7280 (5) | 0.079 (3) | |
C38 | 1.0851 (13) | 0.6725 (3) | 0.6783 (5) | 0.098 (4) | |
C39 | 1.0621 (14) | 0.6555 (4) | 0.5994 (5) | 0.096 (4) | |
C40 | 0.8943 (14) | 0.6070 (4) | 0.5655 (5) | 0.099 (3) | |
C41 | 0.7469 (11) | 0.5766 (3) | 0.6099 (4) | 0.076 (3) | |
C42 | 0.7638 (11) | 0.5937 (3) | 0.6937 (4) | 0.070 (3) | |
H1A | 0.39760 | 1.03920 | 0.67190 | 0.1490* | |
H1B | 0.35650 | 1.12520 | 0.68430 | 0.1490* | |
H2A | 0.27380 | 1.05740 | 0.79360 | 0.1980* | |
H2B | 0.51790 | 1.02440 | 0.80930 | 0.1980* | |
H3A | 0.82430 | 1.10330 | 0.85390 | 0.1850* | |
H3B | 0.78320 | 1.18910 | 0.86690 | 0.1850* | |
H4A | 0.66560 | 1.20470 | 0.73100 | 0.1450* | |
H4B | 0.91050 | 1.17250 | 0.74780 | 0.1450* | |
H5A | 0.85430 | 1.13900 | 0.61410 | 0.1220* | |
H5B | 0.59320 | 1.14300 | 0.58740 | 0.1220* | |
H6A | 0.59760 | 1.00690 | 0.57590 | 0.1230* | |
H6B | 0.70340 | 1.04990 | 0.51000 | 0.1230* | |
H7 | 0.79390 | 0.93400 | 0.65570 | 0.0990* | |
H10 | 1.09900 | 0.90860 | 0.51400 | 0.1140* | |
H11 | 1.32440 | 0.85630 | 0.43200 | 0.1230* | |
H12 | 1.62200 | 0.77870 | 0.48600 | 0.1340* | |
H13 | 1.71280 | 0.76170 | 0.62070 | 0.1130* | |
H15 | 1.62360 | 0.78570 | 0.75760 | 0.1080* | |
H17 | 1.53360 | 0.79990 | 0.88650 | 0.1420* | |
H18 | 1.31310 | 0.84420 | 0.97270 | 0.1570* | |
H19 | 1.00060 | 0.91330 | 0.92510 | 0.1440* | |
H20 | 0.90770 | 0.94250 | 0.79130 | 0.1160* | |
H22A | 0.42270 | 0.30640 | 0.84310 | 0.1250* | |
H22B | 0.18780 | 0.26700 | 0.82130 | 0.1250* | |
H23A | 0.25330 | 0.29600 | 0.95820 | 0.1760* | |
H23B | 0.29020 | 0.38080 | 0.93880 | 0.1760* | |
H24A | −0.02060 | 0.45340 | 0.87550 | 0.1470* | |
H24B | −0.25680 | 0.41450 | 0.85570 | 0.1470* | |
H25A | −0.13120 | 0.33940 | 0.75990 | 0.1130* | |
H25B | −0.09950 | 0.42420 | 0.73920 | 0.1130* | |
H26A | 0.12550 | 0.31530 | 0.67470 | 0.1150* | |
H26B | 0.38300 | 0.32580 | 0.70620 | 0.1150* | |
H27A | 0.23450 | 0.40150 | 0.59010 | 0.1090* | |
H27B | 0.11050 | 0.44920 | 0.64770 | 0.1090* | |
H28 | 0.28310 | 0.53250 | 0.72120 | 0.0930* | |
H31 | 0.38550 | 0.52700 | 0.85650 | 0.1270* | |
H32 | 0.43080 | 0.56190 | 0.98900 | 0.1460* | |
H33 | 0.71720 | 0.64390 | 1.04130 | 0.1480* | |
H34 | 0.96590 | 0.68720 | 0.96600 | 0.1330* | |
H36 | 1.08510 | 0.69420 | 0.82800 | 0.1040* | |
H38 | 1.20080 | 0.70420 | 0.70110 | 0.1170* | |
H39 | 1.15880 | 0.67640 | 0.56800 | 0.1150* | |
H40 | 0.88130 | 0.59470 | 0.51130 | 0.1190* | |
H41 | 0.63450 | 0.54450 | 0.58540 | 0.0910* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.189 (7) | 0.123 (4) | 0.161 (6) | 0.003 (5) | 0.085 (5) | −0.019 (4) |
N1 | 0.086 (5) | 0.067 (3) | 0.122 (5) | −0.005 (3) | 0.022 (4) | −0.006 (3) |
N2 | 0.075 (4) | 0.098 (4) | 0.077 (4) | 0.005 (3) | 0.012 (3) | 0.012 (3) |
C1 | 0.085 (6) | 0.114 (5) | 0.184 (9) | −0.032 (4) | 0.049 (7) | −0.019 (5) |
C2 | 0.210 (11) | 0.141 (8) | 0.178 (9) | −0.054 (7) | 0.127 (9) | −0.034 (7) |
C3 | 0.194 (13) | 0.161 (9) | 0.115 (9) | −0.002 (8) | 0.044 (9) | −0.033 (6) |
C4 | 0.113 (7) | 0.075 (5) | 0.171 (9) | −0.012 (4) | 0.017 (6) | −0.023 (5) |
C5 | 0.093 (6) | 0.102 (5) | 0.110 (6) | −0.004 (4) | 0.018 (5) | 0.029 (5) |
C6 | 0.101 (6) | 0.124 (5) | 0.079 (5) | 0.002 (5) | 0.001 (5) | 0.015 (4) |
C7 | 0.083 (5) | 0.096 (5) | 0.070 (5) | −0.019 (4) | 0.014 (4) | 0.007 (4) |
C8 | 0.060 (5) | 0.075 (4) | 0.086 (6) | −0.024 (4) | −0.002 (5) | 0.011 (4) |
C9 | 0.082 (5) | 0.073 (4) | 0.056 (5) | −0.018 (4) | 0.023 (4) | 0.004 (4) |
C10 | 0.095 (6) | 0.097 (5) | 0.098 (6) | −0.001 (4) | 0.030 (5) | −0.003 (4) |
C11 | 0.120 (7) | 0.109 (6) | 0.076 (5) | −0.010 (5) | 0.009 (5) | 0.008 (4) |
C12 | 0.127 (8) | 0.105 (5) | 0.112 (7) | −0.001 (5) | 0.044 (6) | 0.004 (5) |
C13 | 0.092 (6) | 0.092 (5) | 0.105 (6) | 0.008 (4) | 0.037 (6) | −0.004 (5) |
C14 | 0.081 (6) | 0.062 (4) | 0.095 (6) | −0.004 (4) | 0.014 (5) | 0.019 (4) |
C15 | 0.090 (6) | 0.090 (5) | 0.082 (6) | −0.007 (4) | −0.002 (5) | 0.012 (5) |
C16 | 0.122 (8) | 0.093 (5) | 0.054 (5) | −0.027 (5) | 0.021 (5) | −0.005 (4) |
C17 | 0.100 (7) | 0.146 (7) | 0.111 (8) | −0.003 (5) | 0.021 (6) | −0.011 (6) |
C18 | 0.110 (8) | 0.175 (9) | 0.097 (7) | 0.017 (6) | −0.011 (6) | 0.020 (6) |
C19 | 0.145 (9) | 0.152 (8) | 0.068 (6) | −0.016 (6) | 0.034 (6) | −0.020 (5) |
C20 | 0.084 (6) | 0.111 (6) | 0.097 (7) | 0.007 (4) | 0.021 (5) | −0.007 (5) |
C21 | 0.070 (5) | 0.082 (5) | 0.088 (6) | −0.005 (4) | 0.000 (5) | 0.001 (4) |
O2 | 0.181 (6) | 0.148 (5) | 0.107 (5) | −0.012 (5) | 0.042 (5) | 0.041 (4) |
N3 | 0.068 (4) | 0.072 (3) | 0.083 (4) | 0.010 (3) | 0.006 (3) | 0.003 (3) |
N4 | 0.076 (4) | 0.094 (3) | 0.086 (4) | −0.010 (3) | 0.009 (3) | −0.013 (3) |
C22 | 0.088 (6) | 0.079 (4) | 0.137 (7) | −0.004 (4) | −0.007 (6) | 0.021 (5) |
C23 | 0.159 (10) | 0.148 (7) | 0.113 (8) | −0.007 (8) | −0.037 (8) | 0.040 (6) |
C24 | 0.134 (8) | 0.104 (6) | 0.138 (8) | 0.000 (5) | 0.049 (6) | −0.010 (6) |
C25 | 0.085 (6) | 0.086 (5) | 0.112 (6) | 0.005 (4) | 0.018 (5) | 0.001 (4) |
C26 | 0.084 (5) | 0.071 (4) | 0.133 (7) | −0.015 (4) | 0.016 (5) | −0.028 (4) |
C27 | 0.091 (6) | 0.105 (5) | 0.078 (5) | −0.011 (4) | 0.014 (4) | −0.011 (4) |
C28 | 0.079 (5) | 0.078 (4) | 0.078 (5) | −0.001 (4) | 0.020 (4) | −0.004 (4) |
C29 | 0.075 (5) | 0.050 (3) | 0.086 (6) | −0.001 (3) | 0.009 (5) | −0.003 (4) |
C30 | 0.089 (6) | 0.067 (4) | 0.070 (5) | 0.012 (4) | 0.018 (5) | −0.007 (4) |
C31 | 0.116 (7) | 0.115 (6) | 0.088 (6) | −0.005 (5) | 0.025 (6) | −0.004 (5) |
C32 | 0.136 (8) | 0.152 (8) | 0.082 (7) | −0.023 (6) | 0.029 (6) | −0.023 (5) |
C33 | 0.184 (10) | 0.117 (6) | 0.072 (6) | 0.002 (6) | 0.032 (6) | −0.009 (5) |
C34 | 0.145 (8) | 0.106 (5) | 0.077 (6) | −0.010 (5) | 0.010 (5) | −0.033 (4) |
C35 | 0.093 (6) | 0.062 (4) | 0.082 (6) | 0.004 (4) | 0.011 (5) | −0.011 (4) |
C36 | 0.087 (6) | 0.089 (5) | 0.084 (6) | −0.010 (4) | 0.016 (5) | −0.008 (4) |
C37 | 0.088 (6) | 0.068 (4) | 0.088 (6) | −0.002 (4) | 0.032 (5) | 0.012 (4) |
C38 | 0.105 (7) | 0.074 (4) | 0.112 (7) | 0.003 (4) | 0.014 (6) | −0.015 (5) |
C39 | 0.096 (6) | 0.078 (5) | 0.120 (8) | −0.013 (4) | 0.037 (6) | 0.001 (4) |
C40 | 0.108 (6) | 0.100 (5) | 0.101 (6) | 0.002 (5) | 0.050 (6) | 0.012 (5) |
C41 | 0.082 (5) | 0.086 (4) | 0.059 (5) | 0.010 (3) | 0.010 (4) | −0.003 (3) |
C42 | 0.066 (5) | 0.048 (3) | 0.094 (6) | −0.003 (3) | 0.009 (5) | 0.006 (4) |
O1—C2 | 1.420 (11) | C12—H12 | 0.9300 |
O1—C3 | 1.429 (14) | C13—H13 | 0.9300 |
O2—C23 | 1.393 (13) | C15—H15 | 0.9300 |
O2—C24 | 1.425 (10) | C17—H17 | 0.9300 |
N1—C1 | 1.468 (9) | C18—H18 | 0.9300 |
N1—C5 | 1.477 (9) | C19—H19 | 0.9300 |
N1—C4 | 1.440 (10) | C20—H20 | 0.9300 |
N2—C7 | 1.248 (9) | C22—C23 | 1.512 (12) |
N2—C6 | 1.448 (9) | C24—C25 | 1.492 (11) |
N3—C26 | 1.486 (9) | C26—C27 | 1.513 (9) |
N3—C22 | 1.450 (8) | C28—C29 | 1.472 (9) |
N3—C25 | 1.451 (9) | C29—C30 | 1.419 (9) |
N4—C28 | 1.260 (8) | C29—C42 | 1.412 (9) |
N4—C27 | 1.452 (8) | C30—C31 | 1.428 (11) |
C1—C2 | 1.496 (13) | C30—C35 | 1.432 (10) |
C3—C4 | 1.469 (14) | C31—C32 | 1.361 (12) |
C5—C6 | 1.524 (9) | C32—C33 | 1.406 (13) |
C7—C8 | 1.464 (10) | C33—C34 | 1.350 (13) |
C8—C9 | 1.409 (10) | C34—C35 | 1.425 (12) |
C8—C21 | 1.411 (12) | C35—C36 | 1.383 (11) |
C9—C10 | 1.395 (11) | C36—C37 | 1.377 (12) |
C9—C14 | 1.411 (10) | C37—C38 | 1.441 (11) |
C10—C11 | 1.370 (11) | C37—C42 | 1.398 (10) |
C11—C12 | 1.408 (11) | C38—C39 | 1.349 (12) |
C12—C13 | 1.342 (12) | C39—C40 | 1.381 (11) |
C13—C14 | 1.416 (11) | C40—C41 | 1.368 (11) |
C14—C15 | 1.391 (12) | C41—C42 | 1.432 (9) |
C15—C16 | 1.380 (11) | C22—H22A | 0.9700 |
C16—C21 | 1.413 (12) | C22—H22B | 0.9700 |
C16—C17 | 1.420 (12) | C23—H23A | 0.9700 |
C17—C18 | 1.353 (13) | C23—H23B | 0.9700 |
C18—C19 | 1.364 (14) | C24—H24A | 0.9700 |
C19—C20 | 1.378 (13) | C24—H24B | 0.9700 |
C20—C21 | 1.433 (11) | C25—H25A | 0.9700 |
C1—H1A | 0.9700 | C25—H25B | 0.9700 |
C1—H1B | 0.9700 | C26—H26A | 0.9700 |
C2—H2A | 0.9700 | C26—H26B | 0.9700 |
C2—H2B | 0.9700 | C27—H27A | 0.9700 |
C3—H3A | 0.9700 | C27—H27B | 0.9700 |
C3—H3B | 0.9700 | C28—H28 | 0.9300 |
C4—H4A | 0.9700 | C31—H31 | 0.9300 |
C4—H4B | 0.9700 | C32—H32 | 0.9300 |
C5—H5B | 0.9700 | C33—H33 | 0.9300 |
C5—H5A | 0.9700 | C34—H34 | 0.9300 |
C6—H6A | 0.9700 | C36—H36 | 0.9300 |
C6—H6B | 0.9700 | C38—H38 | 0.9300 |
C7—H7 | 0.9300 | C39—H39 | 0.9300 |
C10—H10 | 0.9300 | C40—H40 | 0.9300 |
C11—H11 | 0.9300 | C41—H41 | 0.9300 |
C2—O1—C3 | 108.5 (7) | C19—C18—H18 | 120.00 |
C23—O2—C24 | 111.1 (7) | C20—C19—H19 | 119.00 |
C1—N1—C5 | 112.4 (6) | C18—C19—H19 | 119.00 |
C4—N1—C5 | 112.8 (5) | C21—C20—H20 | 120.00 |
C1—N1—C4 | 107.0 (6) | C19—C20—H20 | 120.00 |
C6—N2—C7 | 116.7 (6) | N3—C22—C23 | 110.0 (5) |
C22—N3—C25 | 108.5 (5) | O2—C23—C22 | 111.3 (7) |
C22—N3—C26 | 110.8 (5) | O2—C24—C25 | 109.6 (6) |
C25—N3—C26 | 111.4 (5) | N3—C25—C24 | 111.1 (6) |
C27—N4—C28 | 116.4 (5) | N3—C26—C27 | 111.9 (5) |
N1—C1—C2 | 110.1 (7) | N4—C27—C26 | 109.6 (5) |
O1—C2—C1 | 111.7 (7) | N4—C28—C29 | 123.1 (6) |
O1—C3—C4 | 111.0 (8) | C28—C29—C30 | 119.0 (6) |
N1—C4—C3 | 112.3 (6) | C28—C29—C42 | 120.2 (6) |
N1—C5—C6 | 112.1 (5) | C30—C29—C42 | 120.8 (6) |
N2—C6—C5 | 109.6 (5) | C29—C30—C31 | 120.1 (6) |
N2—C7—C8 | 123.3 (6) | C29—C30—C35 | 120.3 (7) |
C9—C8—C21 | 119.9 (6) | C31—C30—C35 | 119.5 (6) |
C7—C8—C21 | 115.1 (6) | C30—C31—C32 | 120.4 (7) |
C7—C8—C9 | 125.0 (7) | C31—C32—C33 | 119.7 (8) |
C8—C9—C10 | 119.3 (6) | C32—C33—C34 | 122.1 (8) |
C10—C9—C14 | 118.9 (6) | C33—C34—C35 | 120.5 (7) |
C8—C9—C14 | 121.7 (7) | C30—C35—C34 | 117.7 (7) |
C9—C10—C11 | 120.4 (6) | C30—C35—C36 | 117.2 (7) |
C10—C11—C12 | 120.1 (7) | C34—C35—C36 | 125.1 (7) |
C11—C12—C13 | 121.1 (7) | C35—C36—C37 | 122.1 (7) |
C12—C13—C14 | 119.7 (7) | C36—C37—C38 | 118.4 (7) |
C9—C14—C13 | 119.8 (7) | C36—C37—C42 | 122.6 (7) |
C13—C14—C15 | 122.3 (7) | C38—C37—C42 | 119.0 (7) |
C9—C14—C15 | 117.9 (7) | C37—C38—C39 | 121.4 (7) |
C14—C15—C16 | 120.6 (7) | C38—C39—C40 | 119.7 (8) |
C15—C16—C21 | 122.8 (7) | C39—C40—C41 | 121.5 (7) |
C17—C16—C21 | 119.5 (8) | C40—C41—C42 | 120.7 (6) |
C15—C16—C17 | 117.6 (8) | C29—C42—C37 | 116.9 (6) |
C16—C17—C18 | 121.6 (8) | C29—C42—C41 | 125.3 (6) |
C17—C18—C19 | 119.8 (8) | C37—C42—C41 | 117.8 (6) |
C18—C19—C20 | 121.6 (9) | N3—C22—H22A | 110.00 |
C19—C20—C21 | 120.8 (8) | N3—C22—H22B | 110.00 |
C8—C21—C20 | 126.3 (7) | C23—C22—H22A | 110.00 |
C16—C21—C20 | 116.7 (7) | C23—C22—H22B | 110.00 |
C8—C21—C16 | 117.0 (7) | H22A—C22—H22B | 108.00 |
C2—C1—H1A | 110.00 | O2—C23—H23A | 109.00 |
C2—C1—H1B | 110.00 | O2—C23—H23B | 109.00 |
N1—C1—H1A | 110.00 | C22—C23—H23A | 109.00 |
N1—C1—H1B | 110.00 | C22—C23—H23B | 109.00 |
H1A—C1—H1B | 108.00 | H23A—C23—H23B | 108.00 |
O1—C2—H2A | 109.00 | O2—C24—H24A | 110.00 |
O1—C2—H2B | 109.00 | O2—C24—H24B | 110.00 |
H2A—C2—H2B | 108.00 | C25—C24—H24A | 110.00 |
C1—C2—H2B | 109.00 | C25—C24—H24B | 110.00 |
C1—C2—H2A | 109.00 | H24A—C24—H24B | 108.00 |
O1—C3—H3B | 109.00 | N3—C25—H25A | 109.00 |
O1—C3—H3A | 109.00 | N3—C25—H25B | 109.00 |
C4—C3—H3B | 109.00 | C24—C25—H25A | 109.00 |
H3A—C3—H3B | 108.00 | C24—C25—H25B | 109.00 |
C4—C3—H3A | 110.00 | H25A—C25—H25B | 108.00 |
C3—C4—H4A | 109.00 | N3—C26—H26A | 109.00 |
C3—C4—H4B | 109.00 | N3—C26—H26B | 109.00 |
N1—C4—H4A | 109.00 | C27—C26—H26A | 109.00 |
N1—C4—H4B | 109.00 | C27—C26—H26B | 109.00 |
H4A—C4—H4B | 108.00 | H26A—C26—H26B | 108.00 |
H5A—C5—H5B | 108.00 | N4—C27—H27A | 110.00 |
N1—C5—H5A | 109.00 | N4—C27—H27B | 110.00 |
N1—C5—H5B | 109.00 | C26—C27—H27A | 110.00 |
C6—C5—H5B | 109.00 | C26—C27—H27B | 110.00 |
C6—C5—H5A | 109.00 | H27A—C27—H27B | 108.00 |
N2—C6—H6B | 110.00 | N4—C28—H28 | 119.00 |
C5—C6—H6A | 110.00 | C29—C28—H28 | 118.00 |
N2—C6—H6A | 110.00 | C30—C31—H31 | 120.00 |
H6A—C6—H6B | 108.00 | C32—C31—H31 | 120.00 |
C5—C6—H6B | 110.00 | C31—C32—H32 | 120.00 |
N2—C7—H7 | 118.00 | C33—C32—H32 | 120.00 |
C8—C7—H7 | 118.00 | C32—C33—H33 | 119.00 |
C11—C10—H10 | 120.00 | C34—C33—H33 | 119.00 |
C9—C10—H10 | 120.00 | C33—C34—H34 | 120.00 |
C10—C11—H11 | 120.00 | C35—C34—H34 | 120.00 |
C12—C11—H11 | 120.00 | C35—C36—H36 | 119.00 |
C11—C12—H12 | 119.00 | C37—C36—H36 | 119.00 |
C13—C12—H12 | 119.00 | C37—C38—H38 | 119.00 |
C14—C13—H13 | 120.00 | C39—C38—H38 | 119.00 |
C12—C13—H13 | 120.00 | C38—C39—H39 | 120.00 |
C16—C15—H15 | 120.00 | C40—C39—H39 | 120.00 |
C14—C15—H15 | 120.00 | C39—C40—H40 | 119.00 |
C16—C17—H17 | 119.00 | C41—C40—H40 | 119.00 |
C18—C17—H17 | 119.00 | C40—C41—H41 | 120.00 |
C17—C18—H18 | 120.00 | C42—C41—H41 | 120.00 |
C3—O1—C2—C1 | −58.4 (9) | C15—C16—C21—C8 | 0.1 (11) |
C2—O1—C3—C4 | 57.9 (9) | C15—C16—C17—C18 | −178.9 (8) |
C23—O2—C24—C25 | 58.5 (8) | C17—C16—C21—C8 | −179.4 (7) |
C24—O2—C23—C22 | −58.3 (9) | C21—C16—C17—C18 | 0.6 (12) |
C4—N1—C5—C6 | 159.8 (6) | C15—C16—C21—C20 | 178.5 (7) |
C5—N1—C1—C2 | 179.0 (6) | C16—C17—C18—C19 | 0.4 (13) |
C1—N1—C5—C6 | −79.2 (7) | C17—C18—C19—C20 | −1.1 (14) |
C4—N1—C1—C2 | −56.7 (8) | C18—C19—C20—C21 | 0.7 (13) |
C1—N1—C4—C3 | 58.0 (9) | C19—C20—C21—C16 | 0.4 (11) |
C5—N1—C4—C3 | −177.9 (7) | C19—C20—C21—C8 | 178.6 (8) |
C6—N2—C7—C8 | 177.3 (6) | N3—C22—C23—O2 | 57.7 (8) |
C7—N2—C6—C5 | 103.0 (7) | O2—C24—C25—N3 | −58.8 (7) |
C26—N3—C25—C24 | −179.6 (5) | N3—C26—C27—N4 | 74.0 (7) |
C26—N3—C22—C23 | −179.0 (6) | N4—C28—C29—C30 | −131.7 (7) |
C25—N3—C26—C27 | 78.9 (6) | N4—C28—C29—C42 | 51.0 (9) |
C25—N3—C22—C23 | −56.4 (7) | C28—C29—C30—C31 | 5.2 (9) |
C22—N3—C26—C27 | −160.2 (5) | C28—C29—C30—C35 | −178.5 (6) |
C22—N3—C25—C24 | 58.2 (6) | C42—C29—C30—C31 | −177.5 (6) |
C28—N4—C27—C26 | −101.1 (6) | C42—C29—C30—C35 | −1.2 (9) |
C27—N4—C28—C29 | 177.7 (6) | C28—C29—C42—C37 | 176.5 (6) |
N1—C1—C2—O1 | 59.5 (9) | C28—C29—C42—C41 | −0.9 (9) |
O1—C3—C4—N1 | −60.2 (9) | C30—C29—C42—C37 | −0.8 (9) |
N1—C5—C6—N2 | −73.5 (7) | C30—C29—C42—C41 | −178.2 (6) |
N2—C7—C8—C9 | −49.0 (10) | C29—C30—C31—C32 | 179.1 (7) |
N2—C7—C8—C21 | 130.6 (7) | C35—C30—C31—C32 | 2.8 (11) |
C21—C8—C9—C10 | 177.8 (6) | C29—C30—C35—C34 | −178.2 (6) |
C7—C8—C9—C14 | −179.0 (6) | C29—C30—C35—C36 | 1.6 (9) |
C7—C8—C21—C20 | 2.1 (10) | C31—C30—C35—C34 | −2.0 (9) |
C7—C8—C21—C16 | −179.7 (6) | C31—C30—C35—C36 | 177.8 (6) |
C9—C8—C21—C20 | −178.3 (7) | C30—C31—C32—C33 | −1.1 (12) |
C7—C8—C9—C10 | −2.6 (9) | C31—C32—C33—C34 | −1.6 (13) |
C21—C8—C9—C14 | 1.4 (9) | C32—C33—C34—C35 | 2.4 (13) |
C9—C8—C21—C16 | −0.1 (10) | C33—C34—C35—C30 | −0.6 (11) |
C10—C9—C14—C15 | −179.1 (6) | C33—C34—C35—C36 | 179.6 (7) |
C14—C9—C10—C11 | −0.9 (9) | C30—C35—C36—C37 | 0.1 (10) |
C8—C9—C14—C13 | 176.6 (6) | C34—C35—C36—C37 | 179.9 (7) |
C10—C9—C14—C13 | 0.2 (9) | C35—C36—C37—C38 | 178.6 (6) |
C8—C9—C10—C11 | −177.4 (6) | C35—C36—C37—C42 | −2.2 (11) |
C8—C9—C14—C15 | −2.7 (9) | C36—C37—C38—C39 | −179.4 (7) |
C9—C10—C11—C12 | 2.1 (10) | C42—C37—C38—C39 | 1.4 (10) |
C10—C11—C12—C13 | −2.7 (11) | C36—C37—C42—C29 | 2.5 (10) |
C11—C12—C13—C14 | 2.0 (11) | C36—C37—C42—C41 | −180.0 (6) |
C12—C13—C14—C15 | 178.5 (7) | C38—C37—C42—C29 | −178.3 (6) |
C12—C13—C14—C9 | −0.8 (10) | C38—C37—C42—C41 | −0.8 (9) |
C13—C14—C15—C16 | −176.6 (7) | C37—C38—C39—C40 | −1.6 (11) |
C9—C14—C15—C16 | 2.6 (10) | C38—C39—C40—C41 | 1.3 (12) |
C14—C15—C16—C17 | 178.0 (7) | C39—C40—C41—C42 | −0.7 (11) |
C14—C15—C16—C21 | −1.4 (12) | C40—C41—C42—C29 | 177.7 (6) |
C17—C16—C21—C20 | −0.9 (11) | C40—C41—C42—C37 | 0.4 (9) |
Cg2 and Cg11 are the centroids of the C8/C9/C14–C16/C21 and C37–C42 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···N2 | 0.93 | 2.44 | 3.039 (8) | 122 |
C33—H33···O1i | 0.93 | 2.59 | 3.344 (12) | 138 |
C41—H41···N4 | 0.93 | 2.48 | 3.044 (8) | 119 |
C13—H13···Cg11ii | 0.93 | 2.73 | 3.567 (7) | 150 |
C38—H38···Cg2 | 0.93 | 2.79 | 3.548 (6) | 139 |
Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) x+1, y, z. |
Cg2 and Cg11 are the centroids of the C8/C9/C14–C16/C21 and C37–C42 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C33—H33···O1i | 0.93 | 2.59 | 3.344 (12) | 138 |
C13—H13···Cg11ii | 0.93 | 2.73 | 3.567 (7) | 150 |
C38—H38···Cg2 | 0.93 | 2.79 | 3.548 (6) | 139 |
Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) x+1, y, z. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). AJ and MMC thank the Shiraz University Research Council for financial support (grant No. 93-GR—SC-23).
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Schiff bases are usually formed by the condensation of a primary amine with an active carbonyl. They are used as pigments and dyes, catalysts, intermediates in organic synthesis, and as polymer stabilisers (Dhar & Taploo, 1982). Schiff bases form an important class of organic compounds with a wide variety of biological properties (Witkop & Ramachandran, 1964). Many studies have been reported regarding the biological activities of Schiff bases, including their anticancer (Solomon & Lowery, 1993), antibacterial (Gerdemann et al., 2002), antifungal, and herbicidal activities. Therefore, Schiff base (I) was synthesized and its X-ray structure is reported here.
As shown in Fig. 1, the asymmetric unit of the title compound (I) consists of two independent molecules (A, B). The anthracene ring systems (C8–C21 and C29–C42) of the both molecules (A, B) are almostly planar [maximum deviations = 0.069 (9) Å for C19 and 0.071 (8) Å for C12 in molecule A, and 0.028 (7) Å for C39 and C30 in molecule B]. They make dihedral angles of 73.4 (2) and 73.3 (2)°, respectively, with the least-squares planes formed by the four C atoms of the morpholine rings (C1–C4/N1/O1 and C22–C25/N3/O2), which adopts a chair conformation. The puckering parameters of the morpholine rings are QT = 0.575 (9) Å, θ = 1.4 (9) °, ϕ = 142 (64) ° for molecule A, and QT = 0.569 (8) Å, θ = 0.0 (8) °, ϕ = 223 (34) ° for molecule B, respectively.
The (C5–C6–N2–C7 and C26–C27–N4–C28) torsion angles of the bridge –C–C–N–C– groups is -103.0 (7) ° for molecule A and 101.1 (6)° for molecule B. The bond lengths and angles in both molecules (A, B) may be regarded as normal, and they are similar with each other.
In the crystal structure, weak C—H···O hydrogen bonds (Table 1, Fig. 2) which connect pairs of molecules into parallel to the c axis, further stabilize the packing supported by C–H···π interactions (Table 1).