Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051896/dn2249sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051896/dn2249Isup2.hkl |
CCDC reference: 667466
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.122
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.79 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.35 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 5.83 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C11 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C18 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Katayama & Oshiyama (1997); Mahajan et al. (1991); Mishra et al. (1998); Cremer & Pople (1975).
1-(amino(phenyl)methyl)naphthalen-2-ol (1 mmol, 0.249 g) was dissolved in anhydrous methanol, the mixture was stirred for several minitutes, 3-(methylthio)propanal (1 mmol 0.104 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 dichloromethane, colorless single crystals of (I) was obtained after 5 d.
All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic), 0.98 Å (methine), 0.96 Å (methyl) and 0.97 Å (methylene) with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl). H atom atom attached to N was 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).
The oxazine derivatives present various applications and widespread potential biological and pharmacological activities such as antimicrobial(Mahajan et al., 1991), antitumor(Katayama & Oshiyama, 1997) and antihistaminic (Mishra et al., 1998). In view of these important properties, the crystal structure of the title compound, (I), has been determined.
The oxazine ring is not planar and displays an half-chair conformation with the puckering parameters: Q= 0.445 (2) Å, θ = 52.9 (2)° and φ= 268.0 (2) °(Cremer & Pople, 1975). The dihedral angle between the benzene ring and the naphthalene ring is 78.65 (7). The bond lengths C18—N1 and C18—O1 in the oxazine ring are 1.421 (2) Å and 1.458 (2) Å respectively.
For related literature, see: Katayama & Oshiyama (1997); Mahajan et al. (1991); Mishra et al. (1998); Cremer & Pople (1975).
Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); 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: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
Fig. 1. Molecular view of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. |
C21H21NOS | F(000) = 712 |
Mr = 335.45 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1680 reflections |
a = 7.2753 (7) Å | θ = 2.5–24.2° |
b = 14.9201 (13) Å | µ = 0.19 mm−1 |
c = 16.4212 (15) Å | T = 298 K |
β = 98.375 (1)° | Block, colorless |
V = 1763.5 (3) Å3 | 0.27 × 0.23 × 0.23 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3655 independent reflections |
Radiation source: fine-focus sealed tube | 2876 reflections with I > 2/s(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 26.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −9→9 |
Tmin = 0.951, Tmax = 0.959 | k = −18→18 |
20758 measured reflections | l = −20→20 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0608P)2 + 0.3947P] where P = (Fo2 + 2Fc2)/3 |
3655 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.22 e Å−3 |
1 restraint | Δρmin = −0.30 e Å−3 |
C21H21NOS | V = 1763.5 (3) Å3 |
Mr = 335.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.2753 (7) Å | µ = 0.19 mm−1 |
b = 14.9201 (13) Å | T = 298 K |
c = 16.4212 (15) Å | 0.27 × 0.23 × 0.23 mm |
β = 98.375 (1)° |
Bruker SMART CCD area-detector diffractometer | 3655 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 2876 reflections with I > 2/s(I) |
Tmin = 0.951, Tmax = 0.959 | Rint = 0.027 |
20758 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 1 restraint |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.22 e Å−3 |
3655 reflections | Δρmin = −0.30 e Å−3 |
221 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 | ||
S1 | 0.14238 (7) | 0.88480 (4) | 0.31146 (3) | 0.06027 (18) | |
O1 | 0.25196 (16) | 0.89873 (8) | 0.05231 (7) | 0.0504 (3) | |
N1 | 0.58022 (19) | 0.87665 (9) | 0.08898 (8) | 0.0436 (3) | |
H1 | 0.599 (3) | 0.9329 (7) | 0.0971 (12) | 0.065* | |
C1 | 0.4372 (2) | 0.87861 (9) | −0.05684 (9) | 0.0386 (3) | |
C2 | 0.2738 (2) | 0.90140 (10) | −0.02920 (10) | 0.0418 (4) | |
C3 | 0.1183 (2) | 0.93206 (12) | −0.08314 (11) | 0.0511 (4) | |
H3 | 0.0104 | 0.9479 | −0.0625 | 0.061* | |
C4 | 0.1246 (2) | 0.93857 (12) | −0.16469 (11) | 0.0539 (4) | |
H4 | 0.0210 | 0.9590 | −0.1997 | 0.065* | |
C5 | 0.2875 (3) | 0.91463 (11) | −0.19755 (10) | 0.0478 (4) | |
C6 | 0.2985 (3) | 0.92130 (12) | −0.28267 (11) | 0.0602 (5) | |
H6 | 0.1968 | 0.9428 | −0.3182 | 0.072* | |
C7 | 0.4539 (4) | 0.89713 (13) | −0.31338 (11) | 0.0663 (6) | |
H7 | 0.4576 | 0.9009 | −0.3696 | 0.080* | |
C8 | 0.6092 (3) | 0.86646 (13) | −0.26024 (12) | 0.0624 (5) | |
H8 | 0.7159 | 0.8503 | −0.2816 | 0.075* | |
C9 | 0.6063 (3) | 0.85996 (12) | −0.17763 (11) | 0.0510 (4) | |
H9 | 0.7111 | 0.8396 | −0.1434 | 0.061* | |
C10 | 0.4449 (2) | 0.88390 (9) | −0.14325 (9) | 0.0405 (3) | |
C11 | 0.6056 (2) | 0.85344 (10) | 0.00404 (9) | 0.0402 (3) | |
H11 | 0.7098 | 0.8893 | −0.0095 | 0.048* | |
C12 | 0.6629 (2) | 0.75561 (11) | 0.00149 (9) | 0.0424 (4) | |
C13 | 0.5476 (2) | 0.69028 (11) | −0.03684 (10) | 0.0487 (4) | |
H13 | 0.4308 | 0.7061 | −0.0639 | 0.058* | |
C14 | 0.6025 (3) | 0.60134 (12) | −0.03570 (13) | 0.0643 (5) | |
H14 | 0.5230 | 0.5582 | −0.0621 | 0.077* | |
C15 | 0.7718 (4) | 0.57695 (16) | 0.00378 (14) | 0.0783 (7) | |
H15 | 0.8073 | 0.5170 | 0.0057 | 0.094* | |
C16 | 0.8897 (4) | 0.64095 (19) | 0.04070 (16) | 0.0933 (9) | |
H16 | 1.0070 | 0.6245 | 0.0667 | 0.112* | |
C17 | 0.8365 (3) | 0.73032 (16) | 0.03989 (13) | 0.0729 (6) | |
H17 | 0.9182 | 0.7733 | 0.0653 | 0.087* | |
C18 | 0.4003 (2) | 0.85325 (11) | 0.10595 (9) | 0.0440 (4) | |
H18 | 0.3838 | 0.7884 | 0.0985 | 0.053* | |
C19 | 0.3727 (2) | 0.87701 (12) | 0.19314 (10) | 0.0497 (4) | |
H19A | 0.4702 | 0.8493 | 0.2316 | 0.060* | |
H19B | 0.3826 | 0.9414 | 0.2004 | 0.060* | |
C20 | 0.1860 (3) | 0.84608 (13) | 0.21210 (11) | 0.0563 (5) | |
H20A | 0.1815 | 0.7811 | 0.2108 | 0.068* | |
H20B | 0.0893 | 0.8683 | 0.1700 | 0.068* | |
C21 | −0.0719 (4) | 0.8270 (2) | 0.31290 (18) | 0.1074 (10) | |
H21A | −0.1599 | 0.8456 | 0.2666 | 0.161* | |
H21B | −0.1196 | 0.8408 | 0.3630 | 0.161* | |
H21C | −0.0515 | 0.7636 | 0.3099 | 0.161* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0599 (3) | 0.0828 (4) | 0.0395 (3) | 0.0056 (2) | 0.0120 (2) | −0.0013 (2) |
O1 | 0.0468 (6) | 0.0636 (7) | 0.0432 (6) | 0.0048 (5) | 0.0144 (5) | 0.0004 (5) |
N1 | 0.0464 (8) | 0.0453 (7) | 0.0394 (7) | −0.0052 (6) | 0.0077 (6) | −0.0083 (6) |
C1 | 0.0437 (8) | 0.0321 (7) | 0.0406 (8) | −0.0016 (6) | 0.0084 (6) | −0.0004 (6) |
C2 | 0.0453 (9) | 0.0400 (8) | 0.0409 (8) | −0.0017 (7) | 0.0093 (7) | −0.0014 (6) |
C3 | 0.0421 (9) | 0.0542 (10) | 0.0571 (10) | 0.0030 (7) | 0.0076 (8) | −0.0020 (8) |
C4 | 0.0503 (10) | 0.0517 (10) | 0.0559 (10) | 0.0028 (8) | −0.0052 (8) | 0.0006 (8) |
C5 | 0.0609 (10) | 0.0382 (8) | 0.0428 (9) | −0.0040 (7) | 0.0025 (7) | −0.0008 (7) |
C6 | 0.0847 (14) | 0.0532 (10) | 0.0393 (9) | −0.0036 (10) | −0.0025 (9) | 0.0021 (8) |
C7 | 0.1079 (17) | 0.0558 (11) | 0.0370 (9) | −0.0052 (11) | 0.0160 (10) | −0.0007 (8) |
C8 | 0.0847 (14) | 0.0576 (11) | 0.0508 (11) | 0.0023 (10) | 0.0295 (10) | −0.0011 (8) |
C9 | 0.0600 (11) | 0.0483 (9) | 0.0473 (9) | 0.0025 (8) | 0.0167 (8) | 0.0011 (7) |
C10 | 0.0507 (9) | 0.0324 (7) | 0.0392 (8) | −0.0028 (6) | 0.0087 (7) | −0.0014 (6) |
C11 | 0.0405 (8) | 0.0431 (8) | 0.0377 (8) | −0.0040 (6) | 0.0079 (6) | −0.0028 (6) |
C12 | 0.0455 (8) | 0.0491 (9) | 0.0332 (7) | 0.0069 (7) | 0.0082 (6) | 0.0008 (6) |
C13 | 0.0508 (9) | 0.0431 (9) | 0.0530 (10) | 0.0024 (7) | 0.0105 (8) | 0.0024 (7) |
C14 | 0.0826 (15) | 0.0451 (10) | 0.0696 (13) | 0.0042 (9) | 0.0255 (11) | 0.0011 (9) |
C15 | 0.1074 (19) | 0.0586 (12) | 0.0715 (14) | 0.0345 (13) | 0.0214 (13) | 0.0102 (11) |
C16 | 0.0943 (19) | 0.102 (2) | 0.0754 (15) | 0.0557 (16) | −0.0145 (13) | −0.0026 (14) |
C17 | 0.0623 (12) | 0.0832 (15) | 0.0656 (12) | 0.0228 (11) | −0.0164 (10) | −0.0176 (11) |
C18 | 0.0497 (9) | 0.0422 (8) | 0.0405 (8) | −0.0015 (7) | 0.0081 (7) | −0.0018 (6) |
C19 | 0.0557 (10) | 0.0533 (10) | 0.0413 (9) | −0.0024 (8) | 0.0110 (8) | −0.0036 (7) |
C20 | 0.0648 (11) | 0.0593 (11) | 0.0477 (10) | −0.0080 (9) | 0.0184 (8) | −0.0074 (8) |
C21 | 0.099 (2) | 0.131 (2) | 0.106 (2) | −0.0306 (18) | 0.0601 (17) | −0.0140 (18) |
S1—C21 | 1.784 (3) | C9—H9 | 0.9300 |
S1—C20 | 1.8020 (17) | C11—C12 | 1.520 (2) |
O1—C2 | 1.3714 (19) | C11—H11 | 0.9800 |
O1—C18 | 1.457 (2) | C12—C13 | 1.377 (2) |
N1—C18 | 1.421 (2) | C12—C17 | 1.380 (2) |
N1—C11 | 1.4745 (19) | C13—C14 | 1.385 (2) |
N1—H1 | 0.857 (9) | C13—H13 | 0.9300 |
C1—C2 | 1.375 (2) | C14—C15 | 1.355 (3) |
C1—C10 | 1.430 (2) | C14—H14 | 0.9300 |
C1—C11 | 1.511 (2) | C15—C16 | 1.365 (4) |
C2—C3 | 1.408 (2) | C15—H15 | 0.9300 |
C3—C4 | 1.350 (2) | C16—C17 | 1.388 (3) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.417 (3) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C19 | 1.516 (2) |
C5—C6 | 1.415 (2) | C18—H18 | 0.9800 |
C5—C10 | 1.421 (2) | C19—C20 | 1.510 (2) |
C6—C7 | 1.352 (3) | C19—H19A | 0.9700 |
C6—H6 | 0.9300 | C19—H19B | 0.9700 |
C7—C8 | 1.400 (3) | C20—H20A | 0.9700 |
C7—H7 | 0.9300 | C20—H20B | 0.9700 |
C8—C9 | 1.363 (2) | C21—H21A | 0.9600 |
C8—H8 | 0.9300 | C21—H21B | 0.9600 |
C9—C10 | 1.421 (2) | C21—H21C | 0.9600 |
C21—S1—C20 | 97.27 (11) | C13—C12—C11 | 122.72 (14) |
C2—O1—C18 | 115.00 (12) | C17—C12—C11 | 119.12 (16) |
C18—N1—C11 | 111.93 (12) | C12—C13—C14 | 121.08 (18) |
C18—N1—H1 | 109.7 (14) | C12—C13—H13 | 119.5 |
C11—N1—H1 | 109.8 (13) | C14—C13—H13 | 119.5 |
C2—C1—C10 | 118.30 (14) | C15—C14—C13 | 120.3 (2) |
C2—C1—C11 | 119.96 (13) | C15—C14—H14 | 119.9 |
C10—C1—C11 | 121.67 (13) | C13—C14—H14 | 119.9 |
O1—C2—C1 | 122.92 (14) | C14—C15—C16 | 119.5 (2) |
O1—C2—C3 | 115.26 (14) | C14—C15—H15 | 120.2 |
C1—C2—C3 | 121.79 (15) | C16—C15—H15 | 120.2 |
C4—C3—C2 | 120.46 (16) | C15—C16—C17 | 120.8 (2) |
C4—C3—H3 | 119.8 | C15—C16—H16 | 119.6 |
C2—C3—H3 | 119.8 | C17—C16—H16 | 119.6 |
C3—C4—C5 | 120.71 (16) | C12—C17—C16 | 120.2 (2) |
C3—C4—H4 | 119.6 | C12—C17—H17 | 119.9 |
C5—C4—H4 | 119.6 | C16—C17—H17 | 119.9 |
C6—C5—C4 | 121.93 (17) | N1—C18—O1 | 112.90 (13) |
C6—C5—C10 | 119.11 (17) | N1—C18—C19 | 112.33 (13) |
C4—C5—C10 | 118.96 (15) | O1—C18—C19 | 105.88 (13) |
C7—C6—C5 | 121.34 (19) | N1—C18—H18 | 108.5 |
C7—C6—H6 | 119.3 | O1—C18—H18 | 108.5 |
C5—C6—H6 | 119.3 | C19—C18—H18 | 108.5 |
C6—C7—C8 | 119.82 (17) | C20—C19—C18 | 111.72 (14) |
C6—C7—H7 | 120.1 | C20—C19—H19A | 109.3 |
C8—C7—H7 | 120.1 | C18—C19—H19A | 109.3 |
C9—C8—C7 | 121.03 (19) | C20—C19—H19B | 109.3 |
C9—C8—H8 | 119.5 | C18—C19—H19B | 109.3 |
C7—C8—H8 | 119.5 | H19A—C19—H19B | 107.9 |
C8—C9—C10 | 120.73 (18) | C19—C20—S1 | 111.79 (12) |
C8—C9—H9 | 119.6 | C19—C20—H20A | 109.3 |
C10—C9—H9 | 119.6 | S1—C20—H20A | 109.3 |
C9—C10—C5 | 117.96 (15) | C19—C20—H20B | 109.3 |
C9—C10—C1 | 122.29 (15) | S1—C20—H20B | 109.3 |
C5—C10—C1 | 119.75 (14) | H20A—C20—H20B | 107.9 |
N1—C11—C1 | 111.50 (12) | S1—C21—H21A | 109.5 |
N1—C11—C12 | 108.91 (12) | S1—C21—H21B | 109.5 |
C1—C11—C12 | 114.81 (13) | H21A—C21—H21B | 109.5 |
N1—C11—H11 | 107.1 | S1—C21—H21C | 109.5 |
C1—C11—H11 | 107.1 | H21A—C21—H21C | 109.5 |
C12—C11—H11 | 107.1 | H21B—C21—H21C | 109.5 |
C13—C12—C17 | 118.15 (17) |
Experimental details
Crystal data | |
Chemical formula | C21H21NOS |
Mr | 335.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 7.2753 (7), 14.9201 (13), 16.4212 (15) |
β (°) | 98.375 (1) |
V (Å3) | 1763.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.27 × 0.23 × 0.23 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.951, 0.959 |
No. of measured, independent and observed [I > 2/s(I)] reflections | 20758, 3655, 2876 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.122, 1.05 |
No. of reflections | 3655 |
No. of parameters | 221 |
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, −0.30 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 1997b).
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The oxazine derivatives present various applications and widespread potential biological and pharmacological activities such as antimicrobial(Mahajan et al., 1991), antitumor(Katayama & Oshiyama, 1997) and antihistaminic (Mishra et al., 1998). In view of these important properties, the crystal structure of the title compound, (I), has been determined.
The oxazine ring is not planar and displays an half-chair conformation with the puckering parameters: Q= 0.445 (2) Å, θ = 52.9 (2)° and φ= 268.0 (2) °(Cremer & Pople, 1975). The dihedral angle between the benzene ring and the naphthalene ring is 78.65 (7). The bond lengths C18—N1 and C18—O1 in the oxazine ring are 1.421 (2) Å and 1.458 (2) Å respectively.