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The title compound, C17H17ClN2O, was synthesized by the reaction of N-(4-methyl­phenyl)-4-chloro-2-nitro­benz­amide and acetone induced by a low-valent titanium reagent (TiCl4/Zn). The dihydropyrimidine ring in the mol­ecule adopts a screw-boat conformation. The mol­ecules are connected by N—H...O hydrogen bonds, forming a linear chain along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030661/ww6303sup1.cif
Contains datablocks 040723A, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030661/ww6303Isup2.hkl
Contains datablock I

CCDC reference: 259858

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.051
  • wR factor = 0.137
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

7-Chloro-2,2-dimethyl-3-(4-methylphenyl)-1,2-dihydroquinazolin-4(3H)-one top
Crystal data top
C17H17ClN2OZ = 2
Mr = 300.78F(000) = 316
Triclinic, P1Dx = 1.296 Mg m3
Hall symbol: -P 1Melting point = 551–553 K
a = 6.886 (1) ÅMo Kα radiation, λ = 0.71070 Å
b = 10.017 (2) ÅCell parameters from 2181 reflections
c = 11.272 (2) Åθ = 3.3–25.3°
α = 89.258 (9)°µ = 0.25 mm1
β = 84.168 (8)°T = 193 K
γ = 85.447 (8)°Block, colorless
V = 771.0 (2) Å30.30 × 0.26 × 0.25 mm
Data collection top
Rigaku Mercury
diffractometer
2795 independent reflections
Radiation source: fine-focus sealed tube2013 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 7.31 pixels mm-1θmax = 25.4°, θmin = 3.3°
ω scansh = 88
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1112
Tmin = 0.929, Tmax = 0.941l = 1313
7618 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0655P)2 + 0.1194P]
where P = (Fo2 + 2Fc2)/3
2795 reflections(Δ/σ)max < 0.001
198 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.84774 (12)0.36843 (8)1.48776 (8)0.0880 (3)
O10.28892 (19)0.26226 (15)1.05349 (14)0.0490 (4)
N10.5883 (2)0.22626 (16)0.95053 (16)0.0404 (4)
N20.8739 (3)0.22452 (19)1.0535 (2)0.0526 (5)
C10.4689 (3)0.26444 (19)1.0497 (2)0.0395 (5)
C20.8031 (3)0.2459 (2)0.9371 (2)0.0492 (6)
C30.7674 (3)0.2761 (2)1.1539 (2)0.0454 (6)
C40.8548 (3)0.2968 (2)1.2583 (2)0.0553 (7)
H40.99220.28011.25980.066*
C50.7390 (4)0.3416 (2)1.3586 (2)0.0544 (6)
C60.5372 (3)0.3668 (2)1.3610 (2)0.0517 (6)
H60.46010.39861.43120.062*
C70.4527 (3)0.34422 (19)1.2582 (2)0.0445 (5)
H70.31470.35931.25830.053*
C80.5640 (3)0.30000 (19)1.1544 (2)0.0396 (5)
C90.4983 (3)0.1932 (2)0.8455 (2)0.0413 (5)
C100.4176 (3)0.2926 (2)0.7751 (2)0.0458 (5)
H100.42090.38400.79570.055*
C110.3322 (3)0.2593 (2)0.6749 (2)0.0514 (6)
H110.27640.32840.62750.062*
C120.3265 (3)0.1263 (2)0.6422 (2)0.0519 (6)
C130.4071 (4)0.0284 (2)0.7145 (2)0.0542 (6)
H130.40450.06310.69400.065*
C140.4913 (3)0.0603 (2)0.8159 (2)0.0503 (6)
H140.54400.00860.86470.060*
C150.9142 (3)0.1411 (3)0.8545 (3)0.0684 (8)
H15A1.05520.14970.85320.103*
H15B0.87490.15450.77380.103*
H15C0.88420.05160.88320.103*
C160.8353 (4)0.3873 (2)0.8902 (3)0.0674 (8)
H16A0.76580.45320.94610.101*
H16B0.78500.39900.81210.101*
H16C0.97560.40030.88230.101*
C170.2296 (4)0.0891 (3)0.5347 (3)0.0721 (8)
H17A0.27750.00210.50990.108*
H17B0.26080.15180.46940.108*
H17C0.08740.09330.55490.108*
H21.002 (4)0.223 (3)1.051 (2)0.067 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0847 (6)0.0828 (5)0.1052 (7)0.0004 (4)0.0533 (5)0.0221 (4)
O10.0218 (7)0.0582 (9)0.0673 (11)0.0025 (6)0.0055 (7)0.0083 (8)
N10.0228 (8)0.0386 (9)0.0594 (12)0.0031 (7)0.0018 (8)0.0007 (8)
N20.0207 (9)0.0537 (12)0.0829 (16)0.0009 (8)0.0062 (10)0.0031 (10)
C10.0242 (10)0.0308 (10)0.0633 (15)0.0017 (8)0.0046 (9)0.0030 (9)
C20.0248 (10)0.0452 (12)0.0768 (17)0.0028 (9)0.0013 (10)0.0056 (11)
C30.0268 (10)0.0357 (11)0.0745 (16)0.0031 (9)0.0089 (11)0.0030 (11)
C40.0329 (12)0.0454 (13)0.092 (2)0.0069 (10)0.0249 (13)0.0006 (13)
C50.0527 (14)0.0389 (12)0.0765 (18)0.0080 (11)0.0263 (13)0.0041 (12)
C60.0483 (13)0.0403 (12)0.0676 (16)0.0032 (10)0.0103 (12)0.0067 (11)
C70.0305 (11)0.0362 (11)0.0674 (16)0.0027 (9)0.0080 (10)0.0018 (10)
C80.0243 (10)0.0305 (10)0.0645 (15)0.0026 (8)0.0071 (9)0.0009 (10)
C90.0303 (10)0.0366 (11)0.0558 (14)0.0035 (9)0.0011 (9)0.0013 (10)
C100.0417 (12)0.0338 (11)0.0608 (15)0.0025 (9)0.0008 (11)0.0028 (10)
C110.0520 (14)0.0440 (13)0.0575 (15)0.0016 (11)0.0041 (11)0.0055 (11)
C120.0472 (13)0.0518 (13)0.0554 (15)0.0037 (11)0.0008 (11)0.0052 (11)
C130.0540 (14)0.0370 (12)0.0709 (17)0.0047 (10)0.0016 (12)0.0075 (12)
C140.0456 (13)0.0368 (12)0.0677 (16)0.0017 (10)0.0041 (11)0.0037 (11)
C150.0342 (12)0.0751 (17)0.092 (2)0.0026 (12)0.0099 (12)0.0094 (15)
C160.0406 (13)0.0568 (15)0.106 (2)0.0155 (11)0.0043 (14)0.0178 (14)
C170.080 (2)0.0712 (18)0.0658 (18)0.0067 (15)0.0112 (15)0.0112 (14)
Geometric parameters (Å, º) top
Cl1—C51.737 (2)C9—C141.382 (3)
O1—C11.237 (2)C9—C101.383 (3)
N1—C11.359 (3)C10—C111.381 (3)
N1—C91.445 (3)C10—H100.9500
N1—C21.500 (2)C11—C121.391 (3)
N2—C31.368 (3)C11—H110.9500
N2—C21.453 (3)C12—C131.385 (3)
N2—H20.88 (3)C12—C171.506 (3)
C1—C81.468 (3)C13—C141.385 (3)
C2—C151.520 (3)C13—H130.9500
C2—C161.530 (3)C14—H140.9500
C3—C41.400 (3)C15—H15A0.9800
C3—C81.401 (3)C15—H15B0.9800
C4—C51.374 (4)C15—H15C0.9800
C4—H40.9500C16—H16A0.9800
C5—C61.390 (3)C16—H16B0.9800
C6—C71.377 (3)C16—H16C0.9800
C6—H60.9500C17—H17A0.9800
C7—C81.389 (3)C17—H17B0.9800
C7—H70.9500C17—H17C0.9800
C1—N1—C9117.95 (16)C10—C9—N1120.85 (18)
C1—N1—C2122.49 (18)C11—C10—C9120.1 (2)
C9—N1—C2118.16 (18)C11—C10—H10119.9
C3—N2—C2120.63 (18)C9—C10—H10119.9
C3—N2—H2117.1 (17)C10—C11—C12121.2 (2)
C2—N2—H2112.9 (17)C10—C11—H11119.4
O1—C1—N1121.46 (19)C12—C11—H11119.4
O1—C1—C8121.6 (2)C13—C12—C11117.7 (2)
N1—C1—C8116.86 (17)C13—C12—C17120.8 (2)
N2—C2—N1107.53 (18)C11—C12—C17121.5 (2)
N2—C2—C15106.76 (19)C14—C13—C12121.8 (2)
N1—C2—C15110.61 (18)C14—C13—H13119.1
N2—C2—C16111.4 (2)C12—C13—H13119.1
N1—C2—C16109.60 (17)C9—C14—C13119.6 (2)
C15—C2—C16110.9 (2)C9—C14—H14120.2
N2—C3—C4121.58 (19)C13—C14—H14120.2
N2—C3—C8119.0 (2)C2—C15—H15A109.5
C4—C3—C8119.3 (2)C2—C15—H15B109.5
C5—C4—C3119.1 (2)H15A—C15—H15B109.5
C5—C4—H4120.4C2—C15—H15C109.5
C3—C4—H4120.4H15A—C15—H15C109.5
C4—C5—C6122.6 (2)H15B—C15—H15C109.5
C4—C5—Cl1119.09 (18)C2—C16—H16A109.5
C6—C5—Cl1118.3 (2)C2—C16—H16B109.5
C7—C6—C5117.7 (2)H16A—C16—H16B109.5
C7—C6—H6121.1C2—C16—H16C109.5
C5—C6—H6121.1H16A—C16—H16C109.5
C6—C7—C8121.74 (19)H16B—C16—H16C109.5
C6—C7—H7119.1C12—C17—H17A109.5
C8—C7—H7119.1C12—C17—H17B109.5
C7—C8—C3119.5 (2)H17A—C17—H17B109.5
C7—C8—C1120.56 (17)C12—C17—H17C109.5
C3—C8—C1119.6 (2)H17A—C17—H17C109.5
C14—C9—C10119.7 (2)H17B—C17—H17C109.5
C14—C9—N1119.46 (19)
C9—N1—C1—O15.0 (3)C6—C7—C8—C1174.13 (19)
C2—N1—C1—O1171.19 (18)N2—C3—C8—C7175.89 (18)
C9—N1—C1—C8178.86 (16)C4—C3—C8—C70.2 (3)
C2—N1—C1—C812.6 (3)N2—C3—C8—C12.4 (3)
C3—N2—C2—N142.8 (3)C4—C3—C8—C1173.25 (18)
C3—N2—C2—C15161.49 (19)O1—C1—C8—C75.9 (3)
C3—N2—C2—C1677.3 (2)N1—C1—C8—C7177.93 (17)
C1—N1—C2—N236.2 (2)O1—C1—C8—C3167.50 (19)
C9—N1—C2—N2157.60 (17)N1—C1—C8—C38.7 (3)
C1—N1—C2—C15152.4 (2)C1—N1—C9—C14103.0 (2)
C9—N1—C2—C1541.4 (3)C2—N1—C9—C1490.2 (2)
C1—N1—C2—C1685.0 (3)C1—N1—C9—C1076.5 (2)
C9—N1—C2—C1681.2 (2)C2—N1—C9—C1090.4 (2)
C2—N2—C3—C4158.4 (2)C14—C9—C10—C110.7 (3)
C2—N2—C3—C826.0 (3)N1—C9—C10—C11179.94 (19)
N2—C3—C4—C5176.3 (2)C9—C10—C11—C120.5 (3)
C8—C3—C4—C50.7 (3)C10—C11—C12—C130.9 (3)
C3—C4—C5—C60.3 (3)C10—C11—C12—C17178.6 (2)
C3—C4—C5—Cl1179.54 (16)C11—C12—C13—C140.2 (3)
C4—C5—C6—C70.6 (3)C17—C12—C13—C14177.9 (2)
Cl1—C5—C6—C7179.54 (16)C10—C9—C14—C131.3 (3)
C5—C6—C7—C81.1 (3)N1—C9—C14—C13179.3 (2)
C6—C7—C8—C30.7 (3)C12—C13—C14—C90.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.88 (3)2.05 (3)2.912 (2)168 (2)
Symmetry code: (i) x+1, y, z.
 

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