Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058734/nc2072sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058734/nc2072Isup2.hkl |
CCDC reference: 674665
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.066
- wR factor = 0.192
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level B DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 0.839 Test value = 0.800 PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 0.84 e/A PLAT230_ALERT_2_B Hirshfeld Test Diff for N21 - C23' .. 11.77 su PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for N21 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C23'
Alert level C DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -0.655 Test value = -0.600 DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -0.65 e/A PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.59 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 9
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Agarwal et al. (1983); Butcher et al. (2007); Büyükgüngör et al. (2007); El-Masry et al. (2000); Hodnett & Dunn (1970); Misra et al. (1981); Narayana et al. (2007); Odabaşoğlu et al. (2007); Pandey et al. (1999); Samadhiya & Halve (2001); Sarojini et al. (2007); Siddiqui et al. (2006); Singh & Dash (1988); Varma et al. (1986); Yathirajan et al. (2007).
A mixture of 4-methyl-3-nitroaniline (1.52 g, 0.01 mol) and 4-(diethylamino)-2-hydroxybenzaldehyde (1.93 g, 0.01 mol) in 35 ml of ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 9 h. On cooling, a solid separated. It was filtered off and recrystallized from acetone (m.p.: 403–407 K). Analysis found: C 65.98, H 6.41, N 12.78%; C18H21N3O3 requires: C 66.04, H 6.47, N 12.84%.
H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C) or U(H) = 1.5 Ueq(Cmethyl)] using a riding model with C—H ranging from 0.95 Å to 0.99 Å. The methyl group bonded to the aromatic ring was allowed to rotate but not to tip. The hydroxyl H atom was freely refined. One of the ethyl chains is disordered over two sites with a site occupation factor of 0.602 (7) for the major occupied site. The bond lengths and angles of the disordered groups were restrained to have the same values as the non-disordered one.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C18H21N3O3 | F(000) = 696 |
Mr = 327.38 | Dx = 1.316 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3157 (4) Å | Cell parameters from 32963 reflections |
b = 22.3708 (10) Å | θ = 2.8–27.5° |
c = 10.3849 (6) Å | µ = 0.09 mm−1 |
β = 103.571 (5)° | T = 173 K |
V = 1652.12 (15) Å3 | Block, orange |
Z = 4 | 0.41 × 0.37 × 0.33 mm |
STOE IPDS II two-circle- diffractometer | 3334 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.6°, θmin = 2.7° |
ω scans | h = −9→9 |
34345 measured reflections | k = −29→28 |
3823 independent reflections | l = −13→12 |
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)] = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.192 | w = 1/[σ2(Fo2) + (0.1026P)2 + 1.2402P] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
3823 reflections | Δρmax = 0.84 e Å−3 |
242 parameters | Δρmin = −0.66 e Å−3 |
9 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.055 (7) |
C18H21N3O3 | V = 1652.12 (15) Å3 |
Mr = 327.38 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.3157 (4) Å | µ = 0.09 mm−1 |
b = 22.3708 (10) Å | T = 173 K |
c = 10.3849 (6) Å | 0.41 × 0.37 × 0.33 mm |
β = 103.571 (5)° |
STOE IPDS II two-circle- diffractometer | 3334 reflections with I > 2σ(I) |
34345 measured reflections | Rint = 0.032 |
3823 independent reflections |
R[F2 > 2σ(F2)] = 0.066 | 9 restraints |
wR(F2) = 0.192 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.84 e Å−3 |
3823 reflections | Δρmin = −0.66 e Å−3 |
242 parameters |
Experimental. ; |
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 | 0.38176 (19) | 0.59715 (6) | 0.59143 (14) | 0.0370 (3) | |
H1 | 0.322 (5) | 0.5734 (15) | 0.526 (3) | 0.081 (10)* | |
O2 | 0.0769 (3) | 0.39185 (11) | −0.12486 (19) | 0.0797 (7) | |
O3 | 0.3429 (2) | 0.43512 (10) | −0.05554 (17) | 0.0634 (5) | |
N1 | 0.3258 (2) | 0.53706 (7) | 0.37122 (14) | 0.0319 (3) | |
N2 | 0.1885 (2) | 0.41980 (8) | −0.04052 (16) | 0.0422 (4) | |
C1 | 0.2115 (2) | 0.49854 (8) | 0.27839 (17) | 0.0313 (4) | |
C2 | 0.2568 (2) | 0.47627 (8) | 0.16421 (17) | 0.0319 (4) | |
H2 | 0.3738 | 0.4860 | 0.1448 | 0.038* | |
C3 | 0.1293 (2) | 0.43970 (8) | 0.07904 (17) | 0.0331 (4) | |
C4 | −0.0456 (3) | 0.42242 (9) | 0.10075 (18) | 0.0363 (4) | |
C5 | −0.0846 (3) | 0.44508 (10) | 0.2170 (2) | 0.0429 (5) | |
H5 | −0.2005 | 0.4348 | 0.2377 | 0.051* | |
C6 | 0.0388 (3) | 0.48186 (9) | 0.30300 (19) | 0.0400 (4) | |
H6 | 0.0054 | 0.4961 | 0.3806 | 0.048* | |
C7 | −0.1915 (3) | 0.38345 (10) | 0.0125 (2) | 0.0460 (5) | |
H7A | −0.2978 | 0.3776 | 0.0536 | 0.069* | |
H7B | −0.1358 | 0.3446 | 0.0005 | 0.069* | |
H7C | −0.2355 | 0.4029 | −0.0738 | 0.069* | |
C8 | 0.4853 (2) | 0.55697 (8) | 0.35579 (16) | 0.0314 (4) | |
H8 | 0.5288 | 0.5445 | 0.2808 | 0.038* | |
C11 | 0.5982 (2) | 0.59736 (7) | 0.44885 (16) | 0.0303 (4) | |
C12 | 0.5429 (2) | 0.61720 (7) | 0.56401 (16) | 0.0289 (4) | |
C13 | 0.6516 (3) | 0.65743 (8) | 0.65132 (18) | 0.0336 (4) | |
H13 | 0.6094 | 0.6708 | 0.7262 | 0.040* | |
C14 | 0.8232 (3) | 0.67875 (10) | 0.6305 (2) | 0.0485 (6) | |
C15 | 0.8784 (3) | 0.65861 (11) | 0.5147 (2) | 0.0545 (6) | |
H15 | 0.9933 | 0.6723 | 0.4976 | 0.065* | |
C16 | 0.7681 (3) | 0.61986 (9) | 0.42803 (19) | 0.0413 (5) | |
H16 | 0.8078 | 0.6078 | 0.3512 | 0.050* | |
N21 | 0.9350 (3) | 0.71679 (12) | 0.7186 (2) | 0.0826 (9) | |
C21 | 0.8793 (3) | 0.74053 (10) | 0.8340 (2) | 0.0443 (5) | |
H21A | 0.9936 | 0.7539 | 0.8991 | 0.053* | |
H21B | 0.8223 | 0.7078 | 0.8756 | 0.053* | |
C22 | 0.7429 (4) | 0.79165 (10) | 0.8061 (3) | 0.0570 (6) | |
H22A | 0.7130 | 0.8047 | 0.8889 | 0.086* | |
H22B | 0.6275 | 0.7787 | 0.7437 | 0.086* | |
H22C | 0.7992 | 0.8249 | 0.7676 | 0.086* | |
C23 | 1.1389 (6) | 0.72798 (15) | 0.7141 (3) | 0.0403 (10) | 0.602 (7) |
H23A | 1.2166 | 0.7372 | 0.8035 | 0.048* | 0.602 (7) |
H23B | 1.1925 | 0.6927 | 0.6787 | 0.048* | 0.602 (7) |
C24 | 1.1300 (7) | 0.78111 (17) | 0.6227 (4) | 0.0508 (11) | 0.602 (7) |
H24A | 1.2571 | 0.7911 | 0.6143 | 0.076* | 0.602 (7) |
H24B | 1.0761 | 0.8154 | 0.6594 | 0.076* | 0.602 (7) |
H24C | 1.0511 | 0.7712 | 0.5353 | 0.076* | 0.602 (7) |
C23' | 1.0482 (7) | 0.7645 (2) | 0.6538 (5) | 0.0332 (13) | 0.398 (7) |
H23C | 1.0022 | 0.7664 | 0.5563 | 0.040* | 0.398 (7) |
H23D | 1.0447 | 0.8048 | 0.6922 | 0.040* | 0.398 (7) |
C24' | 1.2430 (8) | 0.7363 (3) | 0.6948 (6) | 0.0449 (15) | 0.398 (7) |
H24D | 1.3333 | 0.7610 | 0.6621 | 0.067* | 0.398 (7) |
H24E | 1.2396 | 0.6961 | 0.6569 | 0.067* | 0.398 (7) |
H24F | 1.2813 | 0.7338 | 0.7916 | 0.067* | 0.398 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0384 (7) | 0.0395 (7) | 0.0379 (7) | −0.0090 (5) | 0.0184 (6) | −0.0085 (6) |
O2 | 0.0791 (13) | 0.1144 (17) | 0.0515 (10) | −0.0434 (12) | 0.0274 (9) | −0.0426 (11) |
O3 | 0.0452 (9) | 0.0981 (14) | 0.0518 (9) | −0.0122 (9) | 0.0212 (7) | −0.0298 (9) |
N1 | 0.0352 (8) | 0.0312 (7) | 0.0286 (7) | 0.0030 (6) | 0.0062 (6) | −0.0011 (6) |
N2 | 0.0437 (9) | 0.0513 (10) | 0.0318 (8) | −0.0039 (7) | 0.0089 (7) | −0.0086 (7) |
C1 | 0.0333 (8) | 0.0316 (8) | 0.0277 (8) | 0.0048 (6) | 0.0048 (6) | 0.0006 (6) |
C2 | 0.0306 (8) | 0.0351 (9) | 0.0296 (8) | 0.0027 (7) | 0.0064 (6) | 0.0007 (7) |
C3 | 0.0353 (9) | 0.0373 (9) | 0.0256 (8) | 0.0035 (7) | 0.0051 (7) | −0.0004 (7) |
C4 | 0.0340 (9) | 0.0396 (10) | 0.0331 (9) | −0.0006 (7) | 0.0034 (7) | 0.0012 (7) |
C5 | 0.0342 (9) | 0.0546 (12) | 0.0416 (10) | −0.0046 (8) | 0.0125 (8) | −0.0033 (9) |
C6 | 0.0387 (10) | 0.0495 (11) | 0.0341 (9) | 0.0009 (8) | 0.0130 (7) | −0.0055 (8) |
C7 | 0.0405 (10) | 0.0505 (12) | 0.0428 (11) | −0.0081 (9) | 0.0016 (8) | −0.0032 (9) |
C8 | 0.0389 (9) | 0.0300 (8) | 0.0258 (8) | 0.0041 (7) | 0.0085 (7) | 0.0008 (6) |
C11 | 0.0374 (9) | 0.0279 (8) | 0.0271 (8) | 0.0014 (6) | 0.0107 (7) | 0.0010 (6) |
C12 | 0.0334 (8) | 0.0265 (8) | 0.0292 (8) | 0.0007 (6) | 0.0118 (6) | 0.0028 (6) |
C13 | 0.0409 (9) | 0.0336 (9) | 0.0311 (8) | −0.0050 (7) | 0.0178 (7) | −0.0050 (7) |
C14 | 0.0539 (12) | 0.0533 (12) | 0.0470 (11) | −0.0231 (10) | 0.0295 (10) | −0.0202 (9) |
C15 | 0.0573 (13) | 0.0635 (14) | 0.0552 (13) | −0.0289 (11) | 0.0382 (11) | −0.0256 (11) |
C16 | 0.0515 (11) | 0.0436 (10) | 0.0362 (9) | −0.0083 (8) | 0.0248 (8) | −0.0083 (8) |
N21 | 0.0802 (15) | 0.1071 (19) | 0.0811 (16) | −0.0645 (14) | 0.0604 (13) | −0.0646 (15) |
C21 | 0.0471 (11) | 0.0501 (11) | 0.0397 (10) | −0.0118 (9) | 0.0181 (8) | −0.0151 (9) |
C22 | 0.0653 (15) | 0.0449 (12) | 0.0582 (14) | −0.0102 (10) | 0.0090 (11) | 0.0005 (10) |
C23 | 0.036 (2) | 0.0433 (18) | 0.0420 (17) | −0.0064 (14) | 0.0097 (14) | −0.0062 (14) |
C24 | 0.060 (3) | 0.045 (2) | 0.053 (2) | −0.0138 (18) | 0.0234 (19) | −0.0036 (16) |
C23' | 0.032 (2) | 0.028 (2) | 0.043 (3) | −0.0066 (18) | 0.017 (2) | −0.0013 (19) |
C24' | 0.029 (3) | 0.052 (3) | 0.055 (3) | −0.003 (2) | 0.014 (2) | −0.007 (2) |
O1—C12 | 1.353 (2) | C14—N21 | 1.370 (3) |
O1—H1 | 0.89 (3) | C14—C15 | 1.429 (3) |
O2—N2 | 1.220 (2) | C15—C16 | 1.368 (3) |
O3—N2 | 1.225 (2) | C15—H15 | 0.9500 |
N1—C8 | 1.294 (2) | C16—H16 | 0.9500 |
N1—C1 | 1.411 (2) | N21—C21 | 1.454 (3) |
N2—C3 | 1.476 (2) | N21—C23 | 1.524 (4) |
C1—C2 | 1.396 (2) | N21—C23' | 1.593 (6) |
C1—C6 | 1.397 (3) | C21—C22 | 1.501 (3) |
C2—C3 | 1.391 (2) | C21—H21A | 0.9900 |
C2—H2 | 0.9500 | C21—H21B | 0.9900 |
C3—C4 | 1.404 (3) | C22—H22A | 0.9800 |
C4—C5 | 1.399 (3) | C22—H22B | 0.9800 |
C4—C7 | 1.510 (3) | C22—H22C | 0.9800 |
C5—C6 | 1.382 (3) | C23—C24 | 1.513 (5) |
C5—H5 | 0.9500 | C23—H23A | 0.9900 |
C6—H6 | 0.9500 | C23—H23B | 0.9900 |
C7—H7A | 0.9800 | C24—H24A | 0.9800 |
C7—H7B | 0.9800 | C24—H24B | 0.9800 |
C7—H7C | 0.9800 | C24—H24C | 0.9800 |
C8—C11 | 1.435 (2) | C23'—C24' | 1.524 (7) |
C8—H8 | 0.9500 | C23'—H23C | 0.9900 |
C11—C16 | 1.404 (3) | C23'—H23D | 0.9900 |
C11—C12 | 1.420 (2) | C24'—H24D | 0.9800 |
C12—C13 | 1.388 (2) | C24'—H24E | 0.9800 |
C13—C14 | 1.406 (3) | C24'—H24F | 0.9800 |
C13—H13 | 0.9500 | ||
C12—O1—H1 | 109 (2) | C14—C15—H15 | 119.5 |
C8—N1—C1 | 122.18 (15) | C15—C16—C11 | 122.20 (17) |
O2—N2—O3 | 122.25 (18) | C15—C16—H16 | 118.9 |
O2—N2—C3 | 118.63 (17) | C11—C16—H16 | 118.9 |
O3—N2—C3 | 118.95 (16) | C14—N21—C21 | 122.56 (18) |
C2—C1—C6 | 117.71 (16) | C14—N21—C23 | 121.1 (2) |
C2—C1—N1 | 125.28 (16) | C21—N21—C23 | 115.5 (2) |
C6—C1—N1 | 117.01 (15) | C14—N21—C23' | 115.0 (3) |
C3—C2—C1 | 119.52 (16) | C21—N21—C23' | 112.2 (2) |
C3—C2—H2 | 120.2 | N21—C21—C22 | 114.9 (2) |
C1—C2—H2 | 120.2 | N21—C21—H21A | 108.5 |
C2—C3—C4 | 124.06 (16) | C22—C21—H21A | 108.5 |
C2—C3—N2 | 115.27 (16) | N21—C21—H21B | 108.5 |
C4—C3—N2 | 120.67 (16) | C22—C21—H21B | 108.5 |
C5—C4—C3 | 114.64 (17) | H21A—C21—H21B | 107.5 |
C5—C4—C7 | 118.31 (18) | C21—C22—H22A | 109.5 |
C3—C4—C7 | 127.04 (17) | C21—C22—H22B | 109.5 |
C6—C5—C4 | 122.57 (18) | H22A—C22—H22B | 109.5 |
C6—C5—H5 | 118.7 | C21—C22—H22C | 109.5 |
C4—C5—H5 | 118.7 | H22A—C22—H22C | 109.5 |
C5—C6—C1 | 121.49 (17) | H22B—C22—H22C | 109.5 |
C5—C6—H6 | 119.3 | C24—C23—N21 | 104.5 (3) |
C1—C6—H6 | 119.3 | C24—C23—H23A | 110.9 |
C4—C7—H7A | 109.5 | N21—C23—H23A | 110.9 |
C4—C7—H7B | 109.5 | C24—C23—H23B | 110.9 |
H7A—C7—H7B | 109.5 | N21—C23—H23B | 110.9 |
C4—C7—H7C | 109.5 | H23A—C23—H23B | 108.9 |
H7A—C7—H7C | 109.5 | C23—C24—H24A | 109.5 |
H7B—C7—H7C | 109.5 | C23—C24—H24B | 109.5 |
N1—C8—C11 | 121.82 (16) | H24A—C24—H24B | 109.5 |
N1—C8—H8 | 119.1 | C23—C24—H24C | 109.5 |
C11—C8—H8 | 119.1 | H24A—C24—H24C | 109.5 |
C16—C11—C12 | 117.06 (16) | H24B—C24—H24C | 109.5 |
C16—C11—C8 | 120.85 (16) | C24'—C23'—N21 | 98.7 (4) |
C12—C11—C8 | 122.08 (16) | C24'—C23'—H23C | 112.0 |
O1—C12—C13 | 118.13 (15) | N21—C23'—H23C | 112.0 |
O1—C12—C11 | 120.53 (15) | C24'—C23'—H23D | 112.0 |
C13—C12—C11 | 121.34 (16) | N21—C23'—H23D | 112.0 |
C12—C13—C14 | 120.99 (16) | H23C—C23'—H23D | 109.7 |
C12—C13—H13 | 119.5 | C23'—C24'—H24D | 109.5 |
C14—C13—H13 | 119.5 | C23'—C24'—H24E | 109.5 |
N21—C14—C13 | 121.52 (18) | H24D—C24'—H24E | 109.5 |
N21—C14—C15 | 121.00 (18) | C23'—C24'—H24F | 109.5 |
C13—C14—C15 | 117.47 (18) | H24D—C24'—H24F | 109.5 |
C16—C15—C14 | 120.91 (18) | H24E—C24'—H24F | 109.5 |
C16—C15—H15 | 119.5 | ||
C8—N1—C1—C2 | 2.0 (3) | C8—C11—C12—C13 | −178.38 (16) |
C8—N1—C1—C6 | −177.52 (16) | O1—C12—C13—C14 | 178.26 (19) |
C6—C1—C2—C3 | 1.1 (3) | C11—C12—C13—C14 | −1.7 (3) |
N1—C1—C2—C3 | −178.46 (16) | C12—C13—C14—N21 | −177.6 (2) |
C1—C2—C3—C4 | −0.8 (3) | C12—C13—C14—C15 | 1.6 (3) |
C1—C2—C3—N2 | 178.49 (16) | N21—C14—C15—C16 | 178.9 (3) |
O2—N2—C3—C2 | −173.9 (2) | C13—C14—C15—C16 | −0.3 (4) |
O3—N2—C3—C2 | 1.5 (3) | C14—C15—C16—C11 | −0.9 (4) |
O2—N2—C3—C4 | 5.5 (3) | C12—C11—C16—C15 | 0.8 (3) |
O3—N2—C3—C4 | −179.13 (19) | C8—C11—C16—C15 | 179.7 (2) |
C2—C3—C4—C5 | 0.1 (3) | C13—C14—N21—C21 | −3.9 (5) |
N2—C3—C4—C5 | −179.22 (17) | C15—C14—N21—C21 | 176.9 (3) |
C2—C3—C4—C7 | 179.40 (18) | C13—C14—N21—C23 | 165.2 (3) |
N2—C3—C4—C7 | 0.1 (3) | C15—C14—N21—C23 | −13.9 (5) |
C3—C4—C5—C6 | 0.4 (3) | C13—C14—N21—C23' | −146.3 (3) |
C7—C4—C5—C6 | −178.99 (19) | C15—C14—N21—C23' | 34.6 (4) |
C4—C5—C6—C1 | −0.1 (3) | C14—N21—C21—C22 | −78.8 (3) |
C2—C1—C6—C5 | −0.6 (3) | C23—N21—C21—C22 | 111.4 (3) |
N1—C1—C6—C5 | 178.94 (18) | C23'—N21—C21—C22 | 64.4 (3) |
C1—N1—C8—C11 | 178.33 (15) | C14—N21—C23—C24 | 90.6 (4) |
N1—C8—C11—C16 | −178.02 (17) | C21—N21—C23—C24 | −99.5 (3) |
N1—C8—C11—C12 | 0.8 (3) | C23'—N21—C23—C24 | −3.6 (3) |
C16—C11—C12—O1 | −179.47 (16) | C14—N21—C23'—C24' | −105.5 (4) |
C8—C11—C12—O1 | 1.6 (3) | C21—N21—C23'—C24' | 108.3 (3) |
C16—C11—C12—C13 | 0.5 (3) | C23—N21—C23'—C24' | 4.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.89 (3) | 1.80 (3) | 2.6010 (19) | 147 (3) |
Experimental details
Crystal data | |
Chemical formula | C18H21N3O3 |
Mr | 327.38 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 7.3157 (4), 22.3708 (10), 10.3849 (6) |
β (°) | 103.571 (5) |
V (Å3) | 1652.12 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.41 × 0.37 × 0.33 |
Data collection | |
Diffractometer | STOE IPDS II two-circle- diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 34345, 3823, 3334 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.653 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.192, 0.97 |
No. of reflections | 3823 |
No. of parameters | 242 |
No. of restraints | 9 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.84, −0.66 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.89 (3) | 1.80 (3) | 2.6010 (19) | 147 (3) |
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Schiff bases are used as substrates in the preparation of a number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. They are also used as substrates in the preparation of number of biologically active compounds (Siddiqui et al., 2006). Some Schiff base derivatives are also known to have activities such as antimicrobial (El-Masry et al., 2000; Pandey et al., 1999), antifungal (Singh & Dash, 1988; Varma et al., 1986), antitumor (Hodnett & Dunn, 1970; Misra et al., 1981; Agarwal et al., 1983) and as herbicides (Samadhiya & Halve, 2001). The crystal 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 Odabaşoğlu 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), 2-bromo-N'-[(E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate (Narayana et al., 2007), 2-bromo-N'-isopropylidene-5-methoxybenzohydrazide (Sarojini et al., 2007) have been reported. As a part of our ongoing investigations on the synthesis and structure of Schiff bases, we have determined the structure of the title compound (I).
In the structure of the title compound the oxazine ring adopts a half-chair conformation. The molecular conformation is stabilized by an intramolecular O—H···N hydroggen bond. The dihedral angle between the two aromatic rings is 3.97 (12) Å. The nitro groups is almost co planar with the aromatic ring to which it is attached [dihedral angle 6.3 (4)°].