Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055432/dn2255sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055432/dn2255Isup2.hkl |
CCDC reference: 672880
1-(amino(phenyl)methyl)naphthalen-2-ol(1 mmol, 0.249 g) was dissolved in anhydrous methanol, the mixture was stirred for several minitutes, 2,6-dichlorobenzyaldehyde(1 mmol 0.175 g) in methanol (8 ml) was added dropwise and the mixture was stirred at room temperature for 2 h. The product was isolated and recrystallized in methanol, colourless single crystals of (I) was obtained after 3 d.
All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.98 Å (methine) with Uiso(H) = 1.2Ueq(C). H atoms attached to nitrogen has been located in difference Fourier maps and included in the subsequent refinement using restraints (N—H= 0.86 (1) Å with Uiso(H) = 1.5Ueq(N).
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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.
Fig. 1. Molecular view of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radii. |
C24H17Cl2NO | F(000) = 1680 |
Mr = 406.29 | Dx = 1.380 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1420 reflections |
a = 10.8041 (9) Å | θ = 2.2–24.3° |
b = 10.0189 (9) Å | µ = 0.35 mm−1 |
c = 36.119 (3) Å | T = 298 K |
V = 3909.7 (6) Å3 | Block, colourless |
Z = 8 | 0.27 × 0.23 × 0.22 mm |
Bruker SMART APEX CCD area-detector diffractometer | 4060 independent reflections |
Radiation source: sealed tube | 2484 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ϕ and ω scans | θmax = 26.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −13→13 |
Tmin = 0.912, Tmax = 0.928 | k = −12→12 |
43758 measured reflections | l = −45→45 |
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)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0627P)2 + 1.1294P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4060 reflections | Δρmax = 0.22 e Å−3 |
257 parameters | Δρmin = −0.40 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0016 (4) |
C24H17Cl2NO | V = 3909.7 (6) Å3 |
Mr = 406.29 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.8041 (9) Å | µ = 0.35 mm−1 |
b = 10.0189 (9) Å | T = 298 K |
c = 36.119 (3) Å | 0.27 × 0.23 × 0.22 mm |
Bruker SMART APEX CCD area-detector diffractometer | 4060 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 2484 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 0.928 | Rint = 0.047 |
43758 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 1 restraint |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.22 e Å−3 |
4060 reflections | Δρmin = −0.40 e Å−3 |
257 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 | ||
Cl1 | 0.35756 (10) | −0.01015 (9) | 0.47316 (3) | 0.1301 (4) | |
Cl2 | −0.05546 (8) | 0.25328 (10) | 0.42897 (3) | 0.1288 (4) | |
O1 | 0.09492 (15) | 0.05472 (17) | 0.39088 (5) | 0.0714 (5) | |
N1 | 0.24544 (18) | 0.23064 (18) | 0.40158 (5) | 0.0577 (5) | |
H1 | 0.1936 (18) | 0.2944 (18) | 0.4028 (7) | 0.069* | |
C1 | 0.1477 (2) | 0.1169 (2) | 0.45289 (6) | 0.0616 (6) | |
C2 | 0.2172 (3) | 0.0667 (3) | 0.48184 (8) | 0.0848 (9) | |
C3 | 0.1796 (6) | 0.0765 (5) | 0.51820 (10) | 0.1315 (17) | |
H3 | 0.2287 | 0.0428 | 0.5371 | 0.158* | |
C4 | 0.0693 (7) | 0.1363 (6) | 0.52598 (13) | 0.160 (3) | |
H4 | 0.0429 | 0.1420 | 0.5504 | 0.192* | |
C5 | −0.0030 (5) | 0.1882 (4) | 0.49849 (14) | 0.1293 (17) | |
H5 | −0.0779 | 0.2292 | 0.5041 | 0.155* | |
C6 | 0.0363 (3) | 0.1790 (3) | 0.46230 (8) | 0.0840 (8) | |
C7 | 0.1943 (2) | 0.1069 (2) | 0.41385 (6) | 0.0577 (5) | |
H7 | 0.2612 | 0.0409 | 0.4137 | 0.069* | |
C8 | 0.2899 (2) | 0.2203 (2) | 0.36306 (6) | 0.0545 (5) | |
H8 | 0.3082 | 0.3110 | 0.3545 | 0.065* | |
C9 | 0.4104 (2) | 0.1421 (2) | 0.36226 (6) | 0.0564 (6) | |
C10 | 0.5121 (3) | 0.1931 (3) | 0.38075 (8) | 0.0844 (8) | |
H10 | 0.5061 | 0.2749 | 0.3928 | 0.101* | |
C11 | 0.6226 (3) | 0.1236 (5) | 0.38154 (10) | 0.1080 (11) | |
H11 | 0.6904 | 0.1590 | 0.3940 | 0.130* | |
C12 | 0.6325 (3) | 0.0028 (4) | 0.36396 (11) | 0.1008 (11) | |
H12 | 0.7066 | −0.0443 | 0.3649 | 0.121* | |
C13 | 0.5331 (2) | −0.0489 (3) | 0.34496 (8) | 0.0822 (8) | |
H13 | 0.5399 | −0.1302 | 0.3327 | 0.099* | |
C14 | 0.4232 (2) | 0.0211 (2) | 0.34435 (6) | 0.0625 (6) | |
H14 | 0.3560 | −0.0140 | 0.3315 | 0.075* | |
C15 | 0.18997 (19) | 0.1652 (2) | 0.33852 (6) | 0.0547 (5) | |
C16 | 0.0986 (2) | 0.0886 (2) | 0.35411 (7) | 0.0610 (6) | |
C17 | −0.0003 (2) | 0.0385 (3) | 0.33265 (9) | 0.0773 (7) | |
H17 | −0.0624 | −0.0114 | 0.3438 | 0.093* | |
C18 | −0.0047 (3) | 0.0632 (3) | 0.29574 (9) | 0.0852 (8) | |
H18 | −0.0697 | 0.0289 | 0.2818 | 0.102* | |
C19 | 0.0876 (2) | 0.1399 (3) | 0.27812 (8) | 0.0737 (7) | |
C20 | 0.0857 (3) | 0.1656 (3) | 0.23973 (9) | 0.0939 (10) | |
H20 | 0.0224 | 0.1297 | 0.2254 | 0.113* | |
C21 | 0.1733 (4) | 0.2410 (4) | 0.22337 (9) | 0.1035 (11) | |
H21 | 0.1708 | 0.2556 | 0.1980 | 0.124* | |
C22 | 0.2678 (3) | 0.2969 (3) | 0.24464 (7) | 0.0895 (9) | |
H22 | 0.3269 | 0.3509 | 0.2334 | 0.107* | |
C23 | 0.2741 (3) | 0.2731 (3) | 0.28176 (7) | 0.0729 (7) | |
H23 | 0.3383 | 0.3104 | 0.2955 | 0.088* | |
C24 | 0.1852 (2) | 0.1931 (2) | 0.29982 (6) | 0.0609 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1270 (8) | 0.0978 (6) | 0.1654 (9) | 0.0119 (5) | −0.0736 (7) | −0.0025 (6) |
Cl2 | 0.0843 (6) | 0.1073 (7) | 0.1950 (11) | 0.0303 (5) | 0.0179 (6) | 0.0009 (7) |
O1 | 0.0700 (11) | 0.0685 (10) | 0.0757 (11) | −0.0240 (8) | 0.0004 (8) | −0.0048 (8) |
N1 | 0.0622 (11) | 0.0528 (11) | 0.0580 (11) | −0.0092 (9) | 0.0081 (9) | −0.0083 (9) |
C1 | 0.0713 (15) | 0.0489 (12) | 0.0646 (14) | −0.0111 (11) | 0.0114 (12) | −0.0030 (10) |
C2 | 0.119 (2) | 0.0648 (16) | 0.0710 (18) | −0.0322 (16) | −0.0129 (16) | 0.0017 (13) |
C3 | 0.210 (5) | 0.119 (3) | 0.065 (2) | −0.084 (3) | −0.012 (3) | 0.002 (2) |
C4 | 0.269 (8) | 0.130 (4) | 0.082 (3) | −0.111 (5) | 0.069 (4) | −0.040 (3) |
C5 | 0.159 (4) | 0.091 (3) | 0.138 (3) | −0.045 (2) | 0.091 (3) | −0.044 (3) |
C6 | 0.090 (2) | 0.0641 (15) | 0.098 (2) | −0.0122 (14) | 0.0370 (17) | −0.0110 (14) |
C7 | 0.0571 (12) | 0.0524 (12) | 0.0635 (14) | −0.0051 (10) | 0.0047 (11) | −0.0061 (10) |
C8 | 0.0579 (13) | 0.0556 (13) | 0.0499 (12) | −0.0091 (10) | 0.0031 (10) | −0.0052 (10) |
C9 | 0.0503 (12) | 0.0688 (14) | 0.0501 (12) | −0.0107 (11) | 0.0028 (10) | 0.0029 (10) |
C10 | 0.0659 (17) | 0.105 (2) | 0.0820 (18) | −0.0120 (16) | −0.0122 (14) | −0.0117 (16) |
C11 | 0.0606 (19) | 0.146 (3) | 0.118 (3) | −0.018 (2) | −0.0249 (17) | 0.009 (2) |
C12 | 0.0507 (16) | 0.124 (3) | 0.128 (3) | 0.0081 (18) | 0.0072 (17) | 0.032 (2) |
C13 | 0.0639 (17) | 0.0863 (19) | 0.097 (2) | 0.0076 (14) | 0.0183 (15) | 0.0106 (16) |
C14 | 0.0507 (13) | 0.0715 (15) | 0.0654 (14) | −0.0034 (11) | 0.0071 (10) | −0.0002 (12) |
C15 | 0.0493 (12) | 0.0532 (12) | 0.0617 (14) | 0.0032 (10) | −0.0030 (10) | −0.0102 (10) |
C16 | 0.0564 (13) | 0.0573 (13) | 0.0693 (16) | −0.0006 (11) | −0.0041 (11) | −0.0107 (11) |
C17 | 0.0573 (14) | 0.0706 (16) | 0.104 (2) | −0.0080 (12) | −0.0128 (14) | −0.0130 (15) |
C18 | 0.0732 (18) | 0.0804 (18) | 0.102 (2) | 0.0057 (15) | −0.0364 (16) | −0.0224 (16) |
C19 | 0.0710 (16) | 0.0706 (16) | 0.0795 (18) | 0.0176 (14) | −0.0211 (14) | −0.0187 (13) |
C20 | 0.103 (2) | 0.102 (2) | 0.076 (2) | 0.030 (2) | −0.0342 (18) | −0.0223 (17) |
C21 | 0.128 (3) | 0.122 (3) | 0.0605 (18) | 0.041 (2) | −0.016 (2) | −0.0045 (18) |
C22 | 0.104 (2) | 0.102 (2) | 0.0623 (17) | 0.0224 (18) | 0.0041 (16) | 0.0032 (15) |
C23 | 0.0777 (17) | 0.0803 (17) | 0.0608 (15) | 0.0121 (14) | 0.0002 (13) | −0.0053 (13) |
C24 | 0.0617 (14) | 0.0614 (13) | 0.0594 (14) | 0.0156 (12) | −0.0084 (11) | −0.0092 (11) |
Cl1—C2 | 1.729 (4) | C11—C12 | 1.371 (5) |
Cl2—C6 | 1.728 (3) | C11—H11 | 0.9300 |
O1—C16 | 1.371 (3) | C12—C13 | 1.376 (4) |
O1—C7 | 1.454 (3) | C12—H12 | 0.9300 |
N1—C7 | 1.428 (3) | C13—C14 | 1.379 (3) |
N1—C8 | 1.476 (3) | C13—H13 | 0.9300 |
N1—H1 | 0.851 (10) | C14—H14 | 0.9300 |
C1—C2 | 1.382 (4) | C15—C16 | 1.372 (3) |
C1—C6 | 1.397 (4) | C15—C24 | 1.426 (3) |
C1—C7 | 1.500 (3) | C16—C17 | 1.412 (3) |
C2—C3 | 1.378 (5) | C17—C18 | 1.357 (4) |
C3—C4 | 1.363 (7) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—C19 | 1.410 (4) |
C4—C5 | 1.366 (7) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—C20 | 1.411 (4) |
C5—C6 | 1.377 (5) | C19—C24 | 1.418 (3) |
C5—H5 | 0.9300 | C20—C21 | 1.347 (5) |
C7—H7 | 0.9800 | C20—H20 | 0.9300 |
C8—C15 | 1.502 (3) | C21—C22 | 1.396 (5) |
C8—C9 | 1.520 (3) | C21—H21 | 0.9300 |
C8—H8 | 0.9800 | C22—C23 | 1.363 (4) |
C9—C14 | 1.381 (3) | C22—H22 | 0.9300 |
C9—C10 | 1.384 (3) | C23—C24 | 1.411 (4) |
C10—C11 | 1.382 (5) | C23—H23 | 0.9300 |
C10—H10 | 0.9300 | ||
C16—O1—C7 | 116.25 (17) | C12—C11—H11 | 119.9 |
C7—N1—C8 | 110.97 (16) | C10—C11—H11 | 119.9 |
C7—N1—H1 | 112.4 (17) | C11—C12—C13 | 120.2 (3) |
C8—N1—H1 | 108.3 (17) | C11—C12—H12 | 119.9 |
C2—C1—C6 | 116.5 (2) | C13—C12—H12 | 119.9 |
C2—C1—C7 | 120.3 (2) | C12—C13—C14 | 119.2 (3) |
C6—C1—C7 | 123.2 (2) | C12—C13—H13 | 120.4 |
C3—C2—C1 | 122.3 (4) | C14—C13—H13 | 120.4 |
C3—C2—Cl1 | 117.6 (3) | C13—C14—C9 | 121.7 (2) |
C1—C2—Cl1 | 120.1 (2) | C13—C14—H14 | 119.2 |
C4—C3—C2 | 119.1 (5) | C9—C14—H14 | 119.2 |
C4—C3—H3 | 120.5 | C16—C15—C24 | 119.1 (2) |
C2—C3—H3 | 120.5 | C16—C15—C8 | 118.7 (2) |
C3—C4—C5 | 121.2 (4) | C24—C15—C8 | 122.2 (2) |
C3—C4—H4 | 119.4 | O1—C16—C15 | 123.9 (2) |
C5—C4—H4 | 119.4 | O1—C16—C17 | 114.9 (2) |
C4—C5—C6 | 119.2 (5) | C15—C16—C17 | 121.2 (2) |
C4—C5—H5 | 120.4 | C18—C17—C16 | 120.1 (3) |
C6—C5—H5 | 120.4 | C18—C17—H17 | 120.0 |
C5—C6—C1 | 121.8 (4) | C16—C17—H17 | 120.0 |
C5—C6—Cl2 | 117.1 (3) | C17—C18—C19 | 121.2 (2) |
C1—C6—Cl2 | 121.1 (2) | C17—C18—H18 | 119.4 |
N1—C7—O1 | 114.88 (18) | C19—C18—H18 | 119.4 |
N1—C7—C1 | 111.32 (17) | C18—C19—C20 | 122.2 (3) |
O1—C7—C1 | 108.22 (17) | C18—C19—C24 | 118.8 (2) |
N1—C7—H7 | 107.4 | C20—C19—C24 | 119.1 (3) |
O1—C7—H7 | 107.4 | C21—C20—C19 | 121.5 (3) |
C1—C7—H7 | 107.4 | C21—C20—H20 | 119.2 |
N1—C8—C15 | 110.36 (17) | C19—C20—H20 | 119.2 |
N1—C8—C9 | 109.43 (17) | C20—C21—C22 | 119.9 (3) |
C15—C8—C9 | 114.52 (17) | C20—C21—H21 | 120.1 |
N1—C8—H8 | 107.4 | C22—C21—H21 | 120.1 |
C15—C8—H8 | 107.4 | C23—C22—C21 | 120.5 (3) |
C9—C8—H8 | 107.4 | C23—C22—H22 | 119.7 |
C14—C9—C10 | 118.1 (2) | C21—C22—H22 | 119.8 |
C14—C9—C8 | 123.17 (19) | C22—C23—C24 | 121.3 (3) |
C10—C9—C8 | 118.7 (2) | C22—C23—H23 | 119.3 |
C11—C10—C9 | 120.7 (3) | C24—C23—H23 | 119.3 |
C11—C10—H10 | 119.7 | C23—C24—C19 | 117.7 (2) |
C9—C10—H10 | 119.7 | C23—C24—C15 | 122.6 (2) |
C12—C11—C10 | 120.1 (3) | C19—C24—C15 | 119.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl2 | 0.85 (1) | 2.88 (2) | 3.406 (2) | 122 (2) |
Experimental details
Crystal data | |
Chemical formula | C24H17Cl2NO |
Mr | 406.29 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 298 |
a, b, c (Å) | 10.8041 (9), 10.0189 (9), 36.119 (3) |
V (Å3) | 3909.7 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.27 × 0.23 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.912, 0.928 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 43758, 4060, 2484 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.151, 1.05 |
No. of reflections | 4060 |
No. of parameters | 257 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.40 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl2 | 0.851 (10) | 2.88 (2) | 3.406 (2) | 121.6 (19) |
The class of oxazine derivatives is useful heterocyclic compound which is widely used as antimalarial agent(Ren et al.,2001) and a versatile intermediate for the synthesis of carbapenems(Fuganti et al., 1994). Here we present the synthesis and crystal structure of the title compound(I).
The oxazine ring is distorted and adopts a half chair conformation(Fig.1), the dihedral angle between the O1/C15/C16 plane and the N1/C1/C7/C8 plane is 46.08°.
The ring puckering parameters (Cremer & Pople, 1975) for the oxazine are, Q = 0.450 (2) Å, θ = 125.0 (3) ° and ϕ = 298.2 (3) ° indicating an enveloppe conformation. The dichlorophenyl ring makes dihedral angles of 61.27 (18)° and 61.35 (15)° with the benzene ring and the naphthyl system, respectively. The C7—O1 and C7—N1 bond lengths are 1.454 (3) Å and 1.429 (3)\%A. The structure is stabilized by intramolecular N1—H1···Cl2 hydrogen bond(table 1).