Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053135/bt2558sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053135/bt2558Isup2.hkl |
CCDC reference: 672854
A mixture of naphthalen-1-amine (1.43 g, 0.01 mol) and 4-(diethylamino)-2-hydroxybenzaldehyde (1.93 g, 0.01 mol) in 30 ml of ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 5 h (Fig. 4). On cooling, the solid separated was filtered and recrystallized from acetone (m.p.: 371–373 K). Analysis found: C 79.11, H 6.89, N 8.72%; C21H22N2O requires: C 79.21, H 6.96, N 8.80%.
In the absence of anomalous scatterers Friedel pairs had been merged. The hydroxyl hydrogen atom (H10) was located in a difference Fourier map and along with all other all other H atoms placed in their calculated positions and then refined using the riding model with O—H = 0.82 Å and C—H = 0.93 to 0.97 Å, and with Uiso(H) = 1.19–1.49Ueq(C, O). Atoms C17 and C18 are disordered with refined occupancies of 0.4267 (14) [A] and 0.5733 (14) [B], respectively.
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C21H22N2O | F(000) = 340 |
Mr = 318.41 | Dx = 1.209 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 3058 reflections |
a = 7.5329 (5) Å | θ = 4.8–32.5° |
b = 14.6040 (1) Å | µ = 0.08 mm−1 |
c = 7.9904 (5) Å | T = 296 K |
β = 95.951 (6)° | Prism, pale yellow |
V = 874.29 (10) Å3 | 0.47 × 0.42 × 0.35 mm |
Z = 2 |
Oxford Diffraction Gemini R CCD diffractometer | 3003 independent reflections |
Radiation source: fine-focus sealed tube | 1651 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.5°, θmin = 4.8° |
ϕ and ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −21→21 |
Tmin = 0.782, Tmax = 1.000 | l = −11→11 |
8501 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0765P)2] where P = (Fo2 + 2Fc2)/3 |
3003 reflections | (Δ/σ)max = 0.036 |
228 parameters | Δρmax = 0.23 e Å−3 |
1 restraint | Δρmin = −0.22 e Å−3 |
C21H22N2O | V = 874.29 (10) Å3 |
Mr = 318.41 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 7.5329 (5) Å | µ = 0.08 mm−1 |
b = 14.6040 (1) Å | T = 296 K |
c = 7.9904 (5) Å | 0.47 × 0.42 × 0.35 mm |
β = 95.951 (6)° |
Oxford Diffraction Gemini R CCD diffractometer | 3003 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 1651 reflections with I > 2σ(I) |
Tmin = 0.782, Tmax = 1.000 | Rint = 0.022 |
8501 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 1 restraint |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.23 e Å−3 |
3003 reflections | Δρmin = −0.22 e Å−3 |
228 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.44021 (13) | 0.32600 (7) | 0.87995 (13) | 0.0690 (3) | |
H1O | 0.3569 | 0.3617 | 0.8848 | 0.083* | |
N1 | 0.13393 (14) | 0.40391 (7) | 0.78988 (14) | 0.0514 (3) | |
N2 | 0.57713 (17) | 0.04299 (9) | 0.62685 (14) | 0.0650 (4) | |
C1 | 0.00190 (15) | 0.46814 (9) | 0.82282 (15) | 0.0465 (3) | |
C2 | −0.16455 (18) | 0.44247 (11) | 0.86254 (17) | 0.0557 (4) | |
H2A | −0.1983 | 0.3812 | 0.8548 | 0.067* | |
C3 | −0.28310 (18) | 0.50751 (11) | 0.91432 (17) | 0.0597 (4) | |
H3A | −0.3944 | 0.4887 | 0.9420 | 0.072* | |
C4 | −0.23931 (19) | 0.59759 (12) | 0.92512 (18) | 0.0618 (4) | |
H4A | −0.3197 | 0.6398 | 0.9609 | 0.074* | |
C5 | −0.06962 (18) | 0.62741 (10) | 0.88146 (15) | 0.0503 (3) | |
C6 | −0.0191 (2) | 0.72118 (11) | 0.88894 (19) | 0.0647 (4) | |
H6A | −0.0978 | 0.7647 | 0.9234 | 0.078* | |
C7 | 0.1446 (2) | 0.74816 (11) | 0.8459 (2) | 0.0677 (5) | |
H7A | 0.1769 | 0.8096 | 0.8518 | 0.081* | |
C8 | 0.2618 (2) | 0.68327 (11) | 0.79346 (18) | 0.0621 (4) | |
H8A | 0.3719 | 0.7020 | 0.7628 | 0.074* | |
C9 | 0.21839 (18) | 0.59312 (10) | 0.78615 (17) | 0.0528 (4) | |
H9A | 0.2997 | 0.5510 | 0.7517 | 0.063* | |
C10 | 0.05183 (17) | 0.56224 (9) | 0.82993 (14) | 0.0448 (3) | |
C11 | 0.09765 (17) | 0.33416 (9) | 0.69144 (16) | 0.0502 (3) | |
H11A | −0.0150 | 0.3305 | 0.6321 | 0.060* | |
C12 | 0.22364 (17) | 0.26267 (9) | 0.67030 (15) | 0.0470 (3) | |
C13 | 0.39169 (16) | 0.25952 (9) | 0.76692 (15) | 0.0478 (3) | |
C14 | 0.50757 (17) | 0.18848 (10) | 0.75195 (16) | 0.0516 (4) | |
H14A | 0.6171 | 0.1883 | 0.8174 | 0.062* | |
C15 | 0.46460 (17) | 0.11565 (10) | 0.63957 (15) | 0.0494 (3) | |
C16 | 0.29674 (19) | 0.12017 (11) | 0.53899 (17) | 0.0610 (4) | |
H16A | 0.2639 | 0.0741 | 0.4616 | 0.073* | |
C17 | 0.18444 (19) | 0.19213 (10) | 0.55627 (17) | 0.0591 (4) | |
H17A | 0.0765 | 0.1939 | 0.4883 | 0.071* | |
C18A | 0.7636 (6) | 0.0545 (4) | 0.7223 (6) | 0.0672 (7) | 0.356 (3) |
H18A | 0.8217 | 0.1071 | 0.6778 | 0.081* | 0.356 (3) |
H18B | 0.7516 | 0.0662 | 0.8401 | 0.081* | 0.356 (3) |
C19A | 0.8621 (6) | −0.0171 (10) | 0.7100 (9) | 0.187 (3) | 0.356 (3) |
H19A | 0.9649 | −0.0136 | 0.7915 | 0.280* | 0.356 (3) |
H19B | 0.8999 | −0.0200 | 0.5990 | 0.280* | 0.356 (3) |
H19C | 0.7947 | −0.0711 | 0.7304 | 0.280* | 0.356 (3) |
C18B | 0.7214 (3) | 0.0213 (2) | 0.7592 (3) | 0.0672 (7) | 0.644 (3) |
H18C | 0.7000 | −0.0386 | 0.8058 | 0.081* | 0.644 (3) |
H18D | 0.7214 | 0.0659 | 0.8491 | 0.081* | 0.644 (3) |
C19B | 0.9046 (4) | 0.0216 (6) | 0.6908 (5) | 0.187 (3) | 0.644 (3) |
H19D | 0.9947 | 0.0035 | 0.7782 | 0.280* | 0.644 (3) |
H19E | 0.9303 | 0.0821 | 0.6529 | 0.280* | 0.644 (3) |
H19F | 0.9032 | −0.0205 | 0.5984 | 0.280* | 0.644 (3) |
C20 | 0.5237 (2) | −0.03633 (11) | 0.52343 (19) | 0.0613 (4) | |
H20A | 0.6303 | −0.0672 | 0.4942 | 0.074* | |
H20B | 0.4581 | −0.0153 | 0.4197 | 0.074* | |
C21 | 0.4101 (3) | −0.10460 (16) | 0.6054 (3) | 0.1049 (7) | |
H21A | 0.3791 | −0.1541 | 0.5289 | 0.157* | |
H21B | 0.3033 | −0.0751 | 0.6337 | 0.157* | |
H21C | 0.4756 | −0.1281 | 0.7058 | 0.157* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0547 (5) | 0.0600 (6) | 0.0886 (7) | −0.0032 (5) | −0.0097 (5) | −0.0216 (6) |
N1 | 0.0516 (5) | 0.0430 (6) | 0.0596 (6) | −0.0019 (5) | 0.0053 (5) | 0.0035 (5) |
N2 | 0.0665 (7) | 0.0656 (8) | 0.0596 (6) | 0.0245 (6) | −0.0088 (6) | −0.0160 (6) |
C1 | 0.0457 (6) | 0.0477 (7) | 0.0455 (6) | 0.0015 (6) | 0.0024 (5) | 0.0017 (6) |
C2 | 0.0539 (7) | 0.0546 (8) | 0.0587 (7) | −0.0051 (6) | 0.0060 (6) | 0.0070 (6) |
C3 | 0.0477 (7) | 0.0759 (10) | 0.0560 (7) | −0.0026 (7) | 0.0078 (6) | −0.0003 (7) |
C4 | 0.0571 (7) | 0.0722 (10) | 0.0568 (7) | 0.0105 (8) | 0.0089 (6) | −0.0107 (7) |
C5 | 0.0581 (7) | 0.0513 (7) | 0.0416 (6) | 0.0013 (6) | 0.0063 (5) | −0.0057 (5) |
C6 | 0.0795 (9) | 0.0520 (8) | 0.0633 (8) | 0.0069 (8) | 0.0101 (7) | −0.0139 (7) |
C7 | 0.0882 (10) | 0.0440 (7) | 0.0707 (9) | −0.0110 (8) | 0.0076 (8) | −0.0068 (7) |
C8 | 0.0638 (8) | 0.0569 (9) | 0.0658 (8) | −0.0109 (8) | 0.0082 (7) | −0.0003 (7) |
C9 | 0.0526 (7) | 0.0496 (8) | 0.0559 (7) | 0.0010 (6) | 0.0048 (6) | 0.0003 (6) |
C10 | 0.0471 (6) | 0.0496 (7) | 0.0368 (5) | 0.0002 (6) | 0.0006 (5) | −0.0023 (5) |
C11 | 0.0532 (7) | 0.0469 (7) | 0.0493 (6) | 0.0032 (6) | −0.0010 (5) | 0.0041 (6) |
C12 | 0.0514 (6) | 0.0430 (7) | 0.0454 (6) | 0.0007 (6) | −0.0001 (5) | 0.0051 (5) |
C13 | 0.0495 (7) | 0.0433 (7) | 0.0500 (6) | −0.0092 (6) | 0.0030 (6) | −0.0043 (6) |
C14 | 0.0429 (6) | 0.0588 (8) | 0.0518 (7) | −0.0026 (6) | −0.0013 (5) | −0.0021 (6) |
C15 | 0.0494 (7) | 0.0522 (8) | 0.0464 (6) | 0.0020 (6) | 0.0045 (5) | −0.0025 (6) |
C16 | 0.0621 (8) | 0.0622 (8) | 0.0557 (7) | 0.0087 (7) | −0.0086 (6) | −0.0145 (7) |
C17 | 0.0571 (7) | 0.0624 (9) | 0.0536 (7) | 0.0105 (7) | −0.0143 (6) | −0.0084 (7) |
C18A | 0.0683 (12) | 0.0760 (17) | 0.0551 (11) | 0.0169 (12) | −0.0047 (9) | −0.0071 (11) |
C19A | 0.0287 (12) | 0.443 (9) | 0.0883 (16) | −0.048 (3) | 0.0068 (12) | 0.020 (3) |
C18B | 0.0683 (12) | 0.0760 (17) | 0.0551 (11) | 0.0169 (12) | −0.0047 (9) | −0.0071 (11) |
C19B | 0.0287 (12) | 0.443 (9) | 0.0883 (16) | −0.048 (3) | 0.0068 (12) | 0.020 (3) |
C20 | 0.0633 (7) | 0.0632 (9) | 0.0583 (8) | 0.0090 (8) | 0.0102 (6) | −0.0095 (7) |
C21 | 0.1101 (14) | 0.0808 (14) | 0.1280 (16) | −0.0032 (13) | 0.0325 (12) | 0.0187 (13) |
O1—C13 | 1.3503 (16) | C12—C17 | 1.3867 (19) |
O1—H1O | 0.8200 | C12—C13 | 1.4135 (17) |
N1—C11 | 1.2987 (17) | C13—C14 | 1.3691 (19) |
N1—C1 | 1.4116 (17) | C14—C15 | 1.4080 (19) |
N2—C15 | 1.3684 (19) | C14—H14A | 0.9300 |
N2—C20 | 1.455 (2) | C15—C16 | 1.4277 (19) |
N2—C18B | 1.470 (3) | C16—C17 | 1.365 (2) |
N2—C18A | 1.537 (5) | C16—H16A | 0.9300 |
C1—C2 | 1.3769 (18) | C17—H17A | 0.9300 |
C1—C10 | 1.4244 (19) | C18A—C19A | 1.293 (13) |
C2—C3 | 1.396 (2) | C18A—H18A | 0.9700 |
C2—H2A | 0.9300 | C18A—H18B | 0.9700 |
C3—C4 | 1.357 (2) | C19A—H19A | 0.9600 |
C3—H3A | 0.9300 | C19A—H19B | 0.9600 |
C4—C5 | 1.427 (2) | C19A—H19C | 0.9600 |
C4—H4A | 0.9300 | C18B—C19B | 1.536 (4) |
C5—C10 | 1.4108 (19) | C18B—H18C | 0.9700 |
C5—C6 | 1.421 (2) | C18B—H18D | 0.9700 |
C6—C7 | 1.371 (2) | C19B—H19D | 0.9600 |
C6—H6A | 0.9300 | C19B—H19E | 0.9600 |
C7—C8 | 1.389 (2) | C19B—H19F | 0.9600 |
C7—H7A | 0.9300 | C20—C21 | 1.507 (3) |
C8—C9 | 1.356 (2) | C20—H20A | 0.9700 |
C8—H8A | 0.9300 | C20—H20B | 0.9700 |
C9—C10 | 1.4110 (19) | C21—H21A | 0.9600 |
C9—H9A | 0.9300 | C21—H21B | 0.9600 |
C11—C12 | 1.4327 (19) | C21—H21C | 0.9600 |
C11—H11A | 0.9300 | ||
C13—O1—H1O | 109.5 | O1—C13—C12 | 120.46 (12) |
C11—N1—C1 | 121.73 (11) | C14—C13—C12 | 121.33 (11) |
C15—N2—C20 | 121.50 (12) | C13—C14—C15 | 121.45 (11) |
C15—N2—C18B | 122.08 (15) | C13—C14—H14A | 119.3 |
C20—N2—C18B | 112.15 (16) | C15—C14—H14A | 119.3 |
C15—N2—C18A | 114.8 (2) | N2—C15—C14 | 122.00 (11) |
C20—N2—C18A | 123.6 (2) | N2—C15—C16 | 120.89 (12) |
C18B—N2—C18A | 25.5 (2) | C14—C15—C16 | 117.11 (12) |
C2—C1—N1 | 122.56 (13) | C17—C16—C15 | 120.05 (13) |
C2—C1—C10 | 119.77 (12) | C17—C16—H16A | 120.0 |
N1—C1—C10 | 117.40 (11) | C15—C16—H16A | 120.0 |
C1—C2—C3 | 120.60 (14) | C16—C17—C12 | 123.12 (13) |
C1—C2—H2A | 119.7 | C16—C17—H17A | 118.4 |
C3—C2—H2A | 119.7 | C12—C17—H17A | 118.4 |
C4—C3—C2 | 121.33 (13) | C19A—C18A—N2 | 112.1 (5) |
C4—C3—H3A | 119.3 | C19A—C18A—H18A | 109.2 |
C2—C3—H3A | 119.3 | N2—C18A—H18A | 109.2 |
C3—C4—C5 | 119.88 (14) | C19A—C18A—H18B | 109.2 |
C3—C4—H4A | 120.1 | N2—C18A—H18B | 109.2 |
C5—C4—H4A | 120.1 | H18A—C18A—H18B | 107.9 |
C10—C5—C6 | 118.91 (13) | N2—C18B—C19B | 111.6 (2) |
C10—C5—C4 | 119.32 (13) | N2—C18B—H18C | 109.3 |
C6—C5—C4 | 121.77 (14) | C19B—C18B—H18C | 109.3 |
C7—C6—C5 | 120.68 (15) | N2—C18B—H18D | 109.3 |
C7—C6—H6A | 119.7 | C19B—C18B—H18D | 109.3 |
C5—C6—H6A | 119.7 | H18C—C18B—H18D | 108.0 |
C6—C7—C8 | 119.71 (15) | C18B—C19B—H19D | 109.5 |
C6—C7—H7A | 120.1 | C18B—C19B—H19E | 109.5 |
C8—C7—H7A | 120.1 | H19D—C19B—H19E | 109.5 |
C9—C8—C7 | 121.14 (14) | C18B—C19B—H19F | 109.5 |
C9—C8—H8A | 119.4 | H19D—C19B—H19F | 109.5 |
C7—C8—H8A | 119.4 | H19E—C19B—H19F | 109.5 |
C8—C9—C10 | 121.07 (14) | N2—C20—C21 | 114.57 (15) |
C8—C9—H9A | 119.5 | N2—C20—H20A | 108.6 |
C10—C9—H9A | 119.5 | C21—C20—H20A | 108.6 |
C5—C10—C9 | 118.49 (12) | N2—C20—H20B | 108.6 |
C5—C10—C1 | 119.08 (12) | C21—C20—H20B | 108.6 |
C9—C10—C1 | 122.44 (12) | H20A—C20—H20B | 107.6 |
N1—C11—C12 | 122.86 (11) | C20—C21—H21A | 109.5 |
N1—C11—H11A | 118.6 | C20—C21—H21B | 109.5 |
C12—C11—H11A | 118.6 | H21A—C21—H21B | 109.5 |
C17—C12—C13 | 116.90 (12) | C20—C21—H21C | 109.5 |
C17—C12—C11 | 121.35 (12) | H21A—C21—H21C | 109.5 |
C13—C12—C11 | 121.74 (11) | H21B—C21—H21C | 109.5 |
O1—C13—C14 | 118.19 (11) | ||
C11—N1—C1—C2 | 46.16 (18) | C11—C12—C13—O1 | −1.77 (19) |
C11—N1—C1—C10 | −139.83 (12) | C17—C12—C13—C14 | −2.00 (19) |
N1—C1—C2—C3 | 172.06 (12) | C11—C12—C13—C14 | 176.64 (12) |
C10—C1—C2—C3 | −1.81 (19) | O1—C13—C14—C15 | 178.56 (12) |
C1—C2—C3—C4 | 0.8 (2) | C12—C13—C14—C15 | 0.1 (2) |
C2—C3—C4—C5 | 0.6 (2) | C20—N2—C15—C14 | 173.50 (13) |
C3—C4—C5—C10 | −0.97 (19) | C18B—N2—C15—C14 | 18.5 (2) |
C3—C4—C5—C6 | 179.22 (14) | C18A—N2—C15—C14 | −9.3 (3) |
C10—C5—C6—C7 | 0.4 (2) | C20—N2—C15—C16 | −6.1 (2) |
C4—C5—C6—C7 | −179.83 (13) | C18B—N2—C15—C16 | −161.04 (18) |
C5—C6—C7—C8 | 0.4 (2) | C18A—N2—C15—C16 | 171.1 (2) |
C6—C7—C8—C9 | −0.9 (2) | C13—C14—C15—N2 | −178.13 (12) |
C7—C8—C9—C10 | 0.7 (2) | C13—C14—C15—C16 | 1.5 (2) |
C6—C5—C10—C9 | −0.63 (17) | N2—C15—C16—C17 | 178.46 (14) |
C4—C5—C10—C9 | 179.56 (12) | C14—C15—C16—C17 | −1.1 (2) |
C6—C5—C10—C1 | 179.79 (12) | C15—C16—C17—C12 | −0.8 (2) |
C4—C5—C10—C1 | −0.02 (17) | C13—C12—C17—C16 | 2.3 (2) |
C8—C9—C10—C5 | 0.12 (19) | C11—C12—C17—C16 | −176.30 (14) |
C8—C9—C10—C1 | 179.69 (13) | C15—N2—C18A—C19A | 178.1 (5) |
C2—C1—C10—C5 | 1.40 (17) | C20—N2—C18A—C19A | −4.8 (6) |
N1—C1—C10—C5 | −172.78 (10) | C18B—N2—C18A—C19A | 65.1 (6) |
C2—C1—C10—C9 | −178.16 (12) | C15—N2—C18B—C19B | −121.8 (4) |
N1—C1—C10—C9 | 7.66 (17) | C20—N2—C18B—C19B | 81.2 (4) |
C1—N1—C11—C12 | −172.94 (12) | C18A—N2—C18B—C19B | −41.2 (6) |
N1—C11—C12—C17 | −175.92 (13) | C15—N2—C20—C21 | −81.05 (19) |
N1—C11—C12—C13 | 5.5 (2) | C18B—N2—C20—C21 | 76.2 (2) |
C17—C12—C13—O1 | 179.60 (12) | C18A—N2—C20—C21 | 102.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1 | 0.82 | 1.87 | 2.6060 (14) | 148 |
C16—H16A···Cg1ii | 0.93 | 2.84 | 3.6475 (15) | 145 |
C17—H17A···Cg2ii | 0.93 | 2.85 | 3.6502 (15) | 145 |
C19A—H19A···Cg1iiii | 0.88 | 2.88 | 3.747 (7) | 142 |
C19B—H19D···Cg1iiii | 0.88 | 2.88 | 3.688 (4) | 149 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y−1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C21H22N2O |
Mr | 318.41 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 7.5329 (5), 14.6040 (1), 7.9904 (5) |
β (°) | 95.951 (6) |
V (Å3) | 874.29 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.47 × 0.42 × 0.35 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R CCD diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.782, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8501, 3003, 1651 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.129, 0.96 |
No. of reflections | 3003 |
No. of parameters | 228 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.22 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1 | 0.82 | 1.87 | 2.6060 (14) | 148.0 |
C16—H16A···Cg1ii | 0.93 | 2.84 | 3.6475 (15) | 145 |
C17—H17A···Cg2ii | 0.93 | 2.85 | 3.6502 (15) | 145 |
C19A—H19A···Cg1iiii | 0.88 | 2.88 | 3.747 (7) | 142 |
C19B—H19D···Cg1iiii | 0.88 | 2.88 | 3.688 (4) | 149 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y−1/2, −z+2. |
Schiff bases are synthesized from an aromatic amine and a carbonyl compound by nucleophilic addition forming a hemiaminal, followed by a dehydration to generate an imine. Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives are also known to have biological activities such as antimicrobial (El-Masry et al. 2000; Pandey et al. 1999), antifungal (Singh et al. 1988; Varma et al., 1986), antitumor (Hodnett et al. 1970; Misra et al. 1981; Agarwal et al., 1983) and as herbicides (Samadhiya & Halve, 2001). The crysta structures of (E)-2-hydroxy-5-methyl-3-[(4-methyl-2 pyridyl)iminomethyl] benzaldehyde (Büyükgüngör et al., 2007); (E)-2-hydroxy-5-methyl-3-[(2-pyridylimino)methyl]benzaldehyde (Odabasoglu et al. 2007); 1-(4-{[(E)-(4-diethylamino-2-hydroxy phenyl)methylene]amino} phenyl)ethanone (Yathirajan et al. 2007), 2-{(E)-[(2-chloro-5-nitrophenyl)imino]methyl}-5-(diethylamino) phenol (Butcher et al. 2007) have been reported. A new Schiff base, (I), C21H22N2O is prepared and its crystal structure is reported.
The angle between the mean planes of the 1-naphthylimino and 2-methylyphenyl groups is 63.3 (2)° (Fig. 1). The two diethyl extensions from the 5-diethylamino group are twisted in a + and - antiperiplanar conformation. One of the ethyl arms C19—C19 is disordered over two conformations which are constrained to have similar metrical parameters with occupancies of 0.644 (3) [C18B & C19B)] and 0.356 (3) [C18A & C19A], respectively. Crystal packing is stabilized by intermolecular C—H···Cg1/Cg2 packing interactions between Cg1/Cg2-π orbitals of the 1-naphthyl (I/II) rings and hydrogen atoms from a nearby phenyl ring [Cg1/Cg2 = center of gravity of the 1-naphthyl (I/II) rings, respectively] as well as between a disordered ethyl carbon from an ethylamino group and Cg1 (Fig. 2). The molecules are stacked along the b axis in alternate, inverted chains with the 1-naphthyl rings obliquely parallel to the ab face of the unit cell (Fig. 3). Intramolecular interactions between the hydroxyl hydrogen atom and the imino nitrogen atom [O1—H10···N1 = 2.6060 (14) Å] in the asymmetric unit provide additional crystal stability.