Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043632/nc2054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043632/nc2054Isup2.hkl |
CCDC reference: 663741
A mixture of 2-aminobenzohydrazide (0.302 g, 0.002 mol) and 4-chlorobenzaldehyde (0.28 g, 0.002 mol) in 15 ml of absolute ethyl alcohol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h. On cooling, the solid separated was filtered and recrystallized from a solvent mixture (8:2) of ethyl acetate and DMF (m.p.: 466–468 K). Analysis found: C 63.52, H 3.76, N 10.49%; C21H15Cl2N3O requires: C 63.65, H 3.82, N 10.60%.
The C—H atoms were positioned with idealized geometry and were refined isotropic with Ueq(H) = 1.2 Ueq(c) using a riding model with C—H = 0.94 Å for aromatic and C—H = 0.99 Å for methine H atoms. The N—H H atom was located in difference map and was refined isotopic with varying coordinates. One chlorine atom is disordered in two positions and was refined anisotropic using a split model (s.o.f. = 0.143 (3) and 0.857 (3)).
Substituted 2,3-dihydroquinazolin-4(1H)-ones are found to be potent inhibitors of inosine 5'-monophosphate dehydrogenase type II (Birch et al., 2005) and also are found to possess antibacterial (Alaimo & Russel, 1972) and anthelmentic activities (Alaimo & Hatton, 1972). 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 were reported to possess antimicrobial, anti-inflammatory and central nervous system activities. Moreover, Schiff bases are also known to have biological 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; Desai et al., 2001), and also act as herbicides. The crystal structures of 3-(4-bromophenyl)-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one (Shi, Li, Shi, Zhuang & Zhang, 2004), 3-(4-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one (Shi et al., 2004a), 6-chloro-3-(4-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one acetone hemisolvate (Shi et al., 2004b), 7-chloro-2,2-dimethyl-3-(4-methylphenyl)-1,2-dihydroquinazolin-4(3H)-one (Shi, Shi et al., 2004), 2-(4-hydroxy-3-methoxyphenyl)-1-phenethyl-1,2-dihydroquinazolin-4(3H)-one (Swamy & Ravikumar, 2005), 5-chloro-3-hydroxy-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one (Vembu et al., 2006) and 2-(biphenyl-4-yl)-2,3-dihydroquinazolin-4(1H)-one (Chruszcz et al., 2007) have been reported. A new quinazolinone containing Schiff base, C21H15Cl2N3O, has been synthesized and its crystal structure is reported. In our synthesis we expected the formation of 2-amino-N'-[(1E)-(4- chlorophenyl)methylene]benzohydrazide. Instead the aldehyde reacted with both primary amino groups and the cyclized form was created producing the title compound, (I).
The six-membered pyrimidin-4(1H)-one ring within the quinazoline group (C1—C2—C7—N1—C8—N2) is a distorted envleope with Cremer & Pople (1975) puckering parameters Q, θ and φ of 0.4372 (17) Å, 121.2 (2)° and 129.4 (2)°, respectively (Fig. 1). For an ideal envelope conformation, θ and φ are 54.7° and (60n)°, respectively. The angle between the mean planes of the two coplanar 4-chlorophenyl groups is 58.9 (1)°. The angles between the mean planes of the benzyl group of the nonplanar, dihydroquinazolin-4 group and those of the two 4-chlorophenyl groups are 82.0 (6) and 84.3 (3)%, respectively. The torsion angles of the methylene amine linkage [N3–N2–C1–C2 = 159.78 (13)° and N3–C15–C16–C21 = -165.29 (16)°] indicates a significant twist between the dihydroquinazolin-4(1H)-one and attached 4-chlorophenyl group. Crystal packing is stabilized by intermolecular N1—H1A···O1 hydrogen bonding between nearby dihydroquinazolin groups which link the molecules into chains along the b axis of the unit cell (Fig.2).
For related structures, see: Shi et al. (2004a, 2004b); Shi, Li, Shi, Zhuang & Zhang (2004); Shi, Shi et al. (2004); Vembu et al. (2006); Swamy & Ravikumar (2005); Chruszcz et al. (2007). For related literature, see: Hodnett & Dunn (1970); Alaimo & Russel (1972); Alaimo & Hatton (1972); Cremer & Pople (1975); Misra et al. (1981); Varma et al. (1986); Singh & Dash (1988); Pandey et al. (1999); El-Masry et al. (2000); Desai et al. (2001); Birch et al. (2005).
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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H15Cl2N3O | F(000) = 816 |
Mr = 396.26 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4254 reflections |
a = 6.8774 (2) Å | θ = 4.7–32.5° |
b = 13.7315 (3) Å | µ = 0.35 mm−1 |
c = 20.4667 (8) Å | T = 203 K |
β = 97.010 (3)° | Plate, colorless |
V = 1918.36 (10) Å3 | 0.53 × 0.47 × 0.13 mm |
Z = 4 |
Oxford Diffraction Gemini diffractometer | 6303 independent reflections |
Radiation source: fine-focus sealed tube | 2674 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.6°, θmin = 4.7° |
φ and ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −18→20 |
Tmin = 0.926, Tmax = 1.000 | l = −29→30 |
16112 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.63 | w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3 |
6303 reflections | (Δ/σ)max = 0.002 |
252 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C21H15Cl2N3O | V = 1918.36 (10) Å3 |
Mr = 396.26 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.8774 (2) Å | µ = 0.35 mm−1 |
b = 13.7315 (3) Å | T = 203 K |
c = 20.4667 (8) Å | 0.53 × 0.47 × 0.13 mm |
β = 97.010 (3)° |
Oxford Diffraction Gemini diffractometer | 6303 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 2674 reflections with I > 2σ(I) |
Tmin = 0.926, Tmax = 1.000 | Rint = 0.037 |
16112 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.63 | Δρmax = 0.42 e Å−3 |
6303 reflections | Δρmin = −0.40 e Å−3 |
252 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. A disordered chlorine atom, Cl2A [(0.143 (3)] & Cl2B [0.857 (3)], occurs within the singly attached 4-chlorophenyl group to the dihydroquinazolin-4 ring and was refined so that their occupancies summed to 1. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | −0.10011 (6) | 0.67297 (3) | 1.01418 (2) | 0.06572 (16) | |
Cl2A | 0.2071 (12) | 0.0619 (3) | 0.9802 (4) | 0.0822 (5) | 0.143 (3) |
Cl2B | 0.1030 (2) | 0.06077 (5) | 0.94734 (8) | 0.0822 (5) | 0.857 (3) |
O1 | 0.65192 (12) | 0.52725 (6) | 0.74083 (5) | 0.0381 (3) | |
N1 | 0.74123 (16) | 0.23816 (9) | 0.75887 (6) | 0.0327 (3) | |
H1A | 0.7714 (16) | 0.1785 (9) | 0.7664 (6) | 0.034 (4)* | |
N2 | 0.59892 (14) | 0.38310 (7) | 0.79096 (6) | 0.0289 (3) | |
N3 | 0.51282 (17) | 0.43070 (8) | 0.84227 (6) | 0.0365 (3) | |
C1 | 0.68930 (18) | 0.43957 (10) | 0.74828 (7) | 0.0302 (4) | |
C2 | 0.83198 (18) | 0.38806 (9) | 0.71214 (7) | 0.0277 (3) | |
C3 | 0.94084 (19) | 0.43931 (10) | 0.67071 (7) | 0.0392 (4) | |
H3A | 0.9251 | 0.5071 | 0.6663 | 0.047* | |
C4 | 1.0717 (2) | 0.39151 (11) | 0.63603 (8) | 0.0461 (5) | |
H4A | 1.1477 | 0.4266 | 0.6089 | 0.055* | |
C5 | 1.09004 (19) | 0.29123 (11) | 0.64157 (8) | 0.0438 (4) | |
H5A | 1.1773 | 0.2583 | 0.6173 | 0.053* | |
C6 | 0.98294 (18) | 0.23944 (10) | 0.68187 (7) | 0.0366 (4) | |
H6A | 0.9965 | 0.1714 | 0.6849 | 0.044* | |
C7 | 0.85406 (18) | 0.28752 (9) | 0.71830 (7) | 0.0290 (3) | |
C8 | 0.68991 (19) | 0.28985 (9) | 0.81588 (8) | 0.0348 (4) | |
H8A | 0.8092 | 0.3031 | 0.8468 | 0.042* | |
C9 | 0.5468 (2) | 0.23071 (9) | 0.84980 (8) | 0.0311 (4) | |
C10 | 0.5939 (2) | 0.19858 (10) | 0.91276 (9) | 0.0454 (4) | |
H10A | 0.7185 | 0.2122 | 0.9351 | 0.055* | |
C11 | 0.4605 (3) | 0.14606 (11) | 0.94427 (9) | 0.0576 (5) | |
H11A | 0.4933 | 0.1247 | 0.9879 | 0.069* | |
C12 | 0.2817 (3) | 0.12593 (11) | 0.91110 (11) | 0.0555 (5) | |
C13 | 0.2316 (2) | 0.15577 (11) | 0.84789 (11) | 0.0562 (5) | |
H13A | 0.1078 | 0.1407 | 0.8254 | 0.067* | |
C14 | 0.3658 (2) | 0.20870 (10) | 0.81721 (8) | 0.0454 (4) | |
H14A | 0.3326 | 0.2298 | 0.7736 | 0.055* | |
C15 | 0.3577 (2) | 0.47659 (10) | 0.82277 (8) | 0.0366 (4) | |
H15A | 0.3095 | 0.4768 | 0.7778 | 0.044* | |
C16 | 0.2520 (2) | 0.52966 (9) | 0.86972 (8) | 0.0307 (4) | |
C17 | 0.3345 (2) | 0.54820 (10) | 0.93330 (8) | 0.0425 (4) | |
H17A | 0.4655 | 0.5304 | 0.9463 | 0.051* | |
C18 | 0.2287 (2) | 0.59239 (10) | 0.97826 (8) | 0.0448 (4) | |
H18A | 0.2860 | 0.6043 | 1.0216 | 0.054* | |
C19 | 0.0381 (2) | 0.61862 (10) | 0.95834 (9) | 0.0394 (4) | |
C20 | −0.0444 (2) | 0.60432 (11) | 0.89521 (9) | 0.0514 (5) | |
H20A | −0.1738 | 0.6245 | 0.8819 | 0.062* | |
C21 | 0.0633 (2) | 0.55979 (11) | 0.85062 (8) | 0.0464 (4) | |
H21A | 0.0067 | 0.5501 | 0.8069 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0652 (3) | 0.0591 (3) | 0.0796 (4) | 0.0083 (2) | 0.0364 (3) | −0.0211 (3) |
Cl2A | 0.0861 (9) | 0.0506 (3) | 0.1259 (10) | −0.0030 (4) | 0.0771 (8) | 0.0145 (5) |
Cl2B | 0.0861 (9) | 0.0506 (3) | 0.1259 (10) | −0.0030 (4) | 0.0771 (8) | 0.0145 (5) |
O1 | 0.0502 (6) | 0.0192 (6) | 0.0473 (7) | 0.0034 (5) | 0.0154 (5) | 0.0021 (5) |
N1 | 0.0446 (7) | 0.0153 (7) | 0.0414 (9) | 0.0031 (6) | 0.0183 (7) | −0.0006 (7) |
N2 | 0.0390 (7) | 0.0177 (6) | 0.0323 (8) | 0.0055 (5) | 0.0138 (6) | 0.0015 (6) |
N3 | 0.0462 (8) | 0.0272 (7) | 0.0388 (9) | 0.0043 (6) | 0.0159 (7) | 0.0001 (7) |
C1 | 0.0365 (9) | 0.0222 (8) | 0.0316 (10) | −0.0041 (7) | 0.0034 (8) | −0.0022 (8) |
C2 | 0.0347 (8) | 0.0186 (8) | 0.0310 (9) | 0.0002 (6) | 0.0090 (7) | −0.0011 (7) |
C3 | 0.0552 (10) | 0.0225 (8) | 0.0429 (11) | −0.0029 (8) | 0.0178 (9) | 0.0002 (8) |
C4 | 0.0635 (11) | 0.0322 (10) | 0.0486 (12) | −0.0055 (8) | 0.0310 (10) | 0.0003 (9) |
C5 | 0.0521 (10) | 0.0361 (9) | 0.0483 (12) | 0.0003 (8) | 0.0257 (9) | −0.0045 (9) |
C6 | 0.0470 (9) | 0.0213 (8) | 0.0446 (11) | 0.0027 (7) | 0.0179 (9) | −0.0018 (8) |
C7 | 0.0330 (8) | 0.0233 (8) | 0.0317 (10) | −0.0019 (7) | 0.0083 (7) | 0.0002 (8) |
C8 | 0.0403 (9) | 0.0241 (8) | 0.0418 (11) | 0.0034 (7) | 0.0121 (8) | 0.0034 (8) |
C9 | 0.0378 (9) | 0.0201 (8) | 0.0373 (11) | 0.0029 (7) | 0.0125 (8) | 0.0003 (8) |
C10 | 0.0588 (10) | 0.0349 (9) | 0.0422 (12) | −0.0011 (8) | 0.0043 (10) | −0.0027 (9) |
C11 | 0.1026 (15) | 0.0367 (11) | 0.0379 (12) | −0.0006 (11) | 0.0270 (12) | 0.0049 (9) |
C12 | 0.0733 (13) | 0.0266 (9) | 0.0777 (16) | 0.0010 (9) | 0.0538 (13) | 0.0019 (11) |
C13 | 0.0358 (10) | 0.0399 (10) | 0.0956 (18) | −0.0014 (8) | 0.0192 (11) | 0.0007 (11) |
C14 | 0.0478 (10) | 0.0373 (9) | 0.0516 (13) | 0.0035 (8) | 0.0075 (10) | 0.0085 (9) |
C15 | 0.0431 (9) | 0.0319 (9) | 0.0359 (11) | −0.0035 (8) | 0.0090 (8) | 0.0034 (8) |
C16 | 0.0362 (9) | 0.0239 (8) | 0.0330 (10) | 0.0025 (7) | 0.0083 (8) | 0.0005 (8) |
C17 | 0.0409 (9) | 0.0441 (10) | 0.0429 (12) | 0.0172 (8) | 0.0069 (9) | 0.0032 (9) |
C18 | 0.0499 (10) | 0.0464 (10) | 0.0380 (11) | 0.0103 (8) | 0.0054 (9) | −0.0061 (9) |
C19 | 0.0425 (10) | 0.0282 (8) | 0.0507 (12) | 0.0036 (7) | 0.0181 (9) | −0.0056 (9) |
C20 | 0.0324 (9) | 0.0636 (12) | 0.0584 (14) | 0.0069 (8) | 0.0060 (10) | −0.0090 (11) |
C21 | 0.0392 (9) | 0.0562 (10) | 0.0433 (11) | 0.0010 (8) | 0.0030 (9) | −0.0110 (9) |
Cl1—C19 | 1.7410 (14) | C8—H8A | 0.9900 |
Cl2A—C12 | 1.793 (6) | C9—C10 | 1.3630 (19) |
Cl2B—C12 | 1.7556 (17) | C9—C14 | 1.3722 (18) |
O1—C1 | 1.2367 (14) | C10—C11 | 1.386 (2) |
N1—C7 | 1.3815 (16) | C10—H10A | 0.9400 |
N1—C8 | 1.4457 (17) | C11—C12 | 1.359 (2) |
N1—H1A | 0.854 (12) | C11—H11A | 0.9400 |
N2—C1 | 1.3722 (16) | C12—C13 | 1.361 (2) |
N2—N3 | 1.4258 (14) | C13—C14 | 1.384 (2) |
N2—C8 | 1.4878 (15) | C13—H13A | 0.9400 |
N3—C15 | 1.2610 (15) | C14—H14A | 0.9400 |
C1—C2 | 1.4789 (17) | C15—C16 | 1.4677 (18) |
C2—C3 | 1.3892 (17) | C15—H15A | 0.9400 |
C2—C7 | 1.3929 (17) | C16—C21 | 1.3723 (17) |
C3—C4 | 1.3786 (17) | C16—C17 | 1.3786 (18) |
C3—H3A | 0.9400 | C17—C18 | 1.3814 (18) |
C4—C5 | 1.3862 (18) | C17—H17A | 0.9400 |
C4—H4A | 0.9400 | C18—C19 | 1.3724 (18) |
C5—C6 | 1.3699 (17) | C18—H18A | 0.9400 |
C5—H5A | 0.9400 | C19—C20 | 1.361 (2) |
C6—C7 | 1.3924 (16) | C20—C21 | 1.3861 (19) |
C6—H6A | 0.9400 | C20—H20A | 0.9400 |
C8—C9 | 1.5090 (17) | C21—H21A | 0.9400 |
C7—N1—C8 | 117.04 (12) | C9—C10—H10A | 119.5 |
C7—N1—H1A | 115.9 (9) | C11—C10—H10A | 119.5 |
C8—N1—H1A | 113.8 (9) | C12—C11—C10 | 118.91 (16) |
C1—N2—N3 | 118.10 (10) | C12—C11—H11A | 120.5 |
C1—N2—C8 | 120.02 (10) | C10—C11—H11A | 120.5 |
N3—N2—C8 | 109.70 (11) | C11—C12—C13 | 121.48 (16) |
C15—N3—N2 | 114.02 (13) | C11—C12—Cl2B | 122.01 (18) |
O1—C1—N2 | 121.67 (12) | C13—C12—Cl2B | 116.50 (18) |
O1—C1—C2 | 122.99 (13) | C11—C12—Cl2A | 92.0 (3) |
N2—C1—C2 | 115.33 (12) | C13—C12—Cl2A | 146.5 (4) |
C3—C2—C7 | 119.76 (12) | Cl2B—C12—Cl2A | 30.1 (3) |
C3—C2—C1 | 120.20 (12) | C12—C13—C14 | 118.95 (17) |
C7—C2—C1 | 120.03 (13) | C12—C13—H13A | 120.5 |
C4—C3—C2 | 120.50 (13) | C14—C13—H13A | 120.5 |
C4—C3—H3A | 119.7 | C9—C14—C13 | 120.71 (16) |
C2—C3—H3A | 119.7 | C9—C14—H14A | 119.6 |
C3—C4—C5 | 119.29 (14) | C13—C14—H14A | 119.6 |
C3—C4—H4A | 120.4 | N3—C15—C16 | 120.56 (14) |
C5—C4—H4A | 120.4 | N3—C15—H15A | 119.7 |
C6—C5—C4 | 120.99 (14) | C16—C15—H15A | 119.7 |
C6—C5—H5A | 119.5 | C21—C16—C17 | 118.64 (14) |
C4—C5—H5A | 119.5 | C21—C16—C15 | 119.34 (15) |
C5—C6—C7 | 120.02 (13) | C17—C16—C15 | 121.99 (13) |
C5—C6—H6A | 120.0 | C16—C17—C18 | 121.34 (14) |
C7—C6—H6A | 120.0 | C16—C17—H17A | 119.3 |
N1—C7—C6 | 122.02 (12) | C18—C17—H17A | 119.3 |
N1—C7—C2 | 118.53 (12) | C19—C18—C17 | 118.64 (15) |
C6—C7—C2 | 119.41 (13) | C19—C18—H18A | 120.7 |
N1—C8—N2 | 106.24 (12) | C17—C18—H18A | 120.7 |
N1—C8—C9 | 110.14 (11) | C20—C19—C18 | 121.11 (15) |
N2—C8—C9 | 110.50 (10) | C20—C19—Cl1 | 119.17 (13) |
N1—C8—H8A | 110.0 | C18—C19—Cl1 | 119.71 (14) |
N2—C8—H8A | 110.0 | C19—C20—C21 | 119.64 (15) |
C9—C8—H8A | 110.0 | C19—C20—H20A | 120.2 |
C10—C9—C14 | 119.02 (14) | C21—C20—H20A | 120.2 |
C10—C9—C8 | 121.07 (14) | C16—C21—C20 | 120.54 (16) |
C14—C9—C8 | 119.92 (14) | C16—C21—H21A | 119.7 |
C9—C10—C11 | 120.92 (16) | C20—C21—H21A | 119.7 |
C1—N2—N3—C15 | 72.35 (15) | N1—C8—C9—C10 | 117.64 (15) |
C8—N2—N3—C15 | −145.13 (11) | N2—C8—C9—C10 | −125.28 (14) |
N3—N2—C1—O1 | −20.85 (19) | N1—C8—C9—C14 | −62.48 (16) |
C8—N2—C1—O1 | −159.42 (13) | N2—C8—C9—C14 | 54.59 (17) |
N3—N2—C1—C2 | 159.47 (11) | C14—C9—C10—C11 | −1.3 (2) |
C8—N2—C1—C2 | 20.89 (18) | C8—C9—C10—C11 | 178.60 (13) |
O1—C1—C2—C3 | 4.3 (2) | C9—C10—C11—C12 | 0.7 (2) |
N2—C1—C2—C3 | −176.04 (12) | C10—C11—C12—C13 | 0.3 (2) |
O1—C1—C2—C7 | −174.11 (13) | C10—C11—C12—Cl2B | −179.45 (11) |
N2—C1—C2—C7 | 5.58 (19) | C10—C11—C12—Cl2A | 179.9 (2) |
C7—C2—C3—C4 | −0.5 (2) | C11—C12—C13—C14 | −0.7 (2) |
C1—C2—C3—C4 | −178.91 (13) | Cl2B—C12—C13—C14 | 179.05 (11) |
C2—C3—C4—C5 | 1.7 (2) | Cl2A—C12—C13—C14 | −180.0 (3) |
C3—C4—C5—C6 | −1.2 (2) | C10—C9—C14—C13 | 0.8 (2) |
C4—C5—C6—C7 | −0.3 (2) | C8—C9—C14—C13 | −179.04 (12) |
C8—N1—C7—C6 | 150.60 (13) | C12—C13—C14—C9 | 0.1 (2) |
C8—N1—C7—C2 | −31.76 (19) | N2—N3—C15—C16 | −179.84 (11) |
C5—C6—C7—N1 | 179.12 (13) | N3—C15—C16—C21 | −165.09 (13) |
C5—C6—C7—C2 | 1.5 (2) | N3—C15—C16—C17 | 13.2 (2) |
C3—C2—C7—N1 | −178.77 (13) | C21—C16—C17—C18 | 2.7 (2) |
C1—C2—C7—N1 | −0.4 (2) | C15—C16—C17—C18 | −175.57 (13) |
C3—C2—C7—C6 | −1.1 (2) | C16—C17—C18—C19 | −0.5 (2) |
C1—C2—C7—C6 | 177.32 (13) | C17—C18—C19—C20 | −1.9 (2) |
C7—N1—C8—N2 | 53.23 (15) | C17—C18—C19—Cl1 | 179.14 (11) |
C7—N1—C8—C9 | 172.93 (12) | C18—C19—C20—C21 | 2.0 (2) |
C1—N2—C8—N1 | −48.54 (15) | Cl1—C19—C20—C21 | −179.03 (12) |
N3—N2—C8—N1 | 169.77 (10) | C17—C16—C21—C20 | −2.6 (2) |
C1—N2—C8—C9 | −168.00 (13) | C15—C16—C21—C20 | 175.72 (14) |
N3—N2—C8—C9 | 50.31 (15) | C19—C20—C21—C16 | 0.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.854 (12) | 2.153 (13) | 2.9877 (15) | 165.7 (12) |
Symmetry code: (i) −x+3/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C21H15Cl2N3O |
Mr | 396.26 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 203 |
a, b, c (Å) | 6.8774 (2), 13.7315 (3), 20.4667 (8) |
β (°) | 97.010 (3) |
V (Å3) | 1918.36 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.53 × 0.47 × 0.13 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.926, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16112, 6303, 2674 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.757 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.055, 1.63 |
No. of reflections | 6303 |
No. of parameters | 252 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.40 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.854 (12) | 2.153 (13) | 2.9877 (15) | 165.7 (12) |
Symmetry code: (i) −x+3/2, y−1/2, −z+3/2. |
Substituted 2,3-dihydroquinazolin-4(1H)-ones are found to be potent inhibitors of inosine 5'-monophosphate dehydrogenase type II (Birch et al., 2005) and also are found to possess antibacterial (Alaimo & Russel, 1972) and anthelmentic activities (Alaimo & Hatton, 1972). 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 were reported to possess antimicrobial, anti-inflammatory and central nervous system activities. Moreover, Schiff bases are also known to have biological 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; Desai et al., 2001), and also act as herbicides. The crystal structures of 3-(4-bromophenyl)-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one (Shi, Li, Shi, Zhuang & Zhang, 2004), 3-(4-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one (Shi et al., 2004a), 6-chloro-3-(4-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one acetone hemisolvate (Shi et al., 2004b), 7-chloro-2,2-dimethyl-3-(4-methylphenyl)-1,2-dihydroquinazolin-4(3H)-one (Shi, Shi et al., 2004), 2-(4-hydroxy-3-methoxyphenyl)-1-phenethyl-1,2-dihydroquinazolin-4(3H)-one (Swamy & Ravikumar, 2005), 5-chloro-3-hydroxy-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one (Vembu et al., 2006) and 2-(biphenyl-4-yl)-2,3-dihydroquinazolin-4(1H)-one (Chruszcz et al., 2007) have been reported. A new quinazolinone containing Schiff base, C21H15Cl2N3O, has been synthesized and its crystal structure is reported. In our synthesis we expected the formation of 2-amino-N'-[(1E)-(4- chlorophenyl)methylene]benzohydrazide. Instead the aldehyde reacted with both primary amino groups and the cyclized form was created producing the title compound, (I).
The six-membered pyrimidin-4(1H)-one ring within the quinazoline group (C1—C2—C7—N1—C8—N2) is a distorted envleope with Cremer & Pople (1975) puckering parameters Q, θ and φ of 0.4372 (17) Å, 121.2 (2)° and 129.4 (2)°, respectively (Fig. 1). For an ideal envelope conformation, θ and φ are 54.7° and (60n)°, respectively. The angle between the mean planes of the two coplanar 4-chlorophenyl groups is 58.9 (1)°. The angles between the mean planes of the benzyl group of the nonplanar, dihydroquinazolin-4 group and those of the two 4-chlorophenyl groups are 82.0 (6) and 84.3 (3)%, respectively. The torsion angles of the methylene amine linkage [N3–N2–C1–C2 = 159.78 (13)° and N3–C15–C16–C21 = -165.29 (16)°] indicates a significant twist between the dihydroquinazolin-4(1H)-one and attached 4-chlorophenyl group. Crystal packing is stabilized by intermolecular N1—H1A···O1 hydrogen bonding between nearby dihydroquinazolin groups which link the molecules into chains along the b axis of the unit cell (Fig.2).