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The title compound, C16H15BrN2O, was synthesized by the reaction of N-(4-bromo­phenyl)-2-nitro­benz­amide and acetone, induced by a low-valent titanium reagent (TiCl4/Zn). The di­hydro­pyrimidine ring 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/S1600536804025115/ob6417sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025115/ob6417Isup2.hkl
Contains datablock I

CCDC reference: 255890

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.027
  • wR factor = 0.068
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT352_ALERT_3_C Short N-H Bond (0.87A) N2 - H2 ... 0.75 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16B .. BR1 .. 3.02 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 2 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.

3-(4-Bromophenyl)-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one top
Crystal data top
C16H15BrN2OZ = 2
Mr = 331.21F(000) = 336
Triclinic, P1Dx = 1.516 Mg m3
Hall symbol: -p 1Melting point = 537–538 K
a = 6.8865 (6) ÅMo Kα radiation, λ = 0.71070 Å
b = 9.9508 (6) ÅCell parameters from 2946 reflections
c = 11.6702 (8) Åθ = 3.5–25.3°
α = 65.397 (4)°µ = 2.83 mm1
β = 88.452 (6)°T = 193 K
γ = 86.194 (6)°Block, colorless
V = 725.51 (9) Å30.50 × 0.30 × 0.16 mm
Data collection top
Rigaku Mercury
diffractometer
2623 independent reflections
Radiation source: fine-focus sealed tube2325 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 7.31 pixels mm-1θmax = 25.4°, θmin = 3.5°
ω scansh = 78
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1111
Tmin = 0.332, Tmax = 0.660l = 1214
7155 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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0402P)2]
where P = (Fo2 + 2Fc2)/3
2623 reflections(Δ/σ)max = 0.002
188 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.50 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
Br10.32962 (3)0.18161 (2)1.02521 (2)0.03688 (11)
O10.16653 (19)0.28373 (17)0.45556 (14)0.0312 (4)
N10.1215 (2)0.19553 (18)0.55721 (15)0.0204 (4)
N20.4172 (3)0.2491 (2)0.44279 (18)0.0273 (4)
C10.0132 (3)0.2848 (2)0.45484 (19)0.0205 (4)
C20.3339 (3)0.2146 (2)0.56747 (19)0.0242 (5)
C30.3246 (3)0.3513 (2)0.3383 (2)0.0228 (4)
C40.4222 (3)0.4264 (3)0.2243 (2)0.0316 (5)
H40.55910.41020.21960.038*
C50.3210 (3)0.5230 (3)0.1196 (2)0.0335 (5)
H50.38940.57320.04330.040*
C60.1204 (3)0.5491 (2)0.1227 (2)0.0305 (5)
H60.05200.61690.04980.037*
C70.0230 (3)0.4746 (2)0.2335 (2)0.0254 (5)
H70.11420.49090.23670.030*
C80.1217 (3)0.3761 (2)0.34075 (19)0.0209 (4)
C90.0184 (3)0.1062 (2)0.66984 (19)0.0211 (4)
C100.0021 (3)0.0420 (2)0.6987 (2)0.0255 (5)
H100.05340.08440.64500.031*
C110.1030 (3)0.1284 (2)0.8054 (2)0.0269 (5)
H110.11750.23010.82540.032*
C120.1826 (3)0.0645 (2)0.88246 (19)0.0242 (4)
C130.1625 (3)0.0825 (2)0.8558 (2)0.0274 (5)
H130.21630.12420.91040.033*
C140.0627 (3)0.1683 (2)0.7480 (2)0.0257 (5)
H140.04980.27020.72760.031*
C150.4351 (3)0.0722 (3)0.6580 (2)0.0349 (5)
H15A0.40940.00800.63350.052*
H15B0.38610.04830.74350.052*
H15C0.57560.08360.65580.052*
C160.3563 (3)0.3399 (3)0.6087 (2)0.0318 (5)
H16A0.49480.35310.61460.048*
H16B0.29470.31500.69110.048*
H16C0.29360.43190.54670.048*
H20.525 (4)0.253 (3)0.443 (2)0.030 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03586 (16)0.03531 (16)0.02981 (16)0.00680 (11)0.01102 (11)0.00393 (11)
O10.0149 (7)0.0383 (9)0.0335 (9)0.0022 (6)0.0017 (6)0.0081 (7)
N10.0151 (8)0.0226 (9)0.0226 (9)0.0037 (7)0.0024 (7)0.0082 (7)
N20.0118 (9)0.0415 (11)0.0293 (11)0.0020 (8)0.0028 (8)0.0156 (9)
C10.0184 (10)0.0197 (10)0.0253 (11)0.0023 (8)0.0024 (9)0.0113 (9)
C20.0162 (10)0.0308 (12)0.0252 (11)0.0055 (9)0.0012 (9)0.0106 (9)
C30.0199 (10)0.0265 (11)0.0260 (11)0.0050 (9)0.0032 (9)0.0146 (9)
C40.0220 (11)0.0437 (14)0.0316 (13)0.0099 (10)0.0089 (10)0.0176 (11)
C50.0397 (13)0.0358 (13)0.0267 (12)0.0150 (11)0.0123 (10)0.0136 (10)
C60.0409 (13)0.0238 (11)0.0253 (12)0.0026 (10)0.0014 (10)0.0086 (9)
C70.0240 (10)0.0233 (11)0.0300 (12)0.0011 (9)0.0015 (9)0.0125 (9)
C80.0203 (10)0.0211 (10)0.0241 (11)0.0034 (8)0.0025 (9)0.0121 (9)
C90.0183 (10)0.0226 (11)0.0219 (11)0.0033 (8)0.0014 (8)0.0085 (9)
C100.0286 (11)0.0243 (11)0.0268 (12)0.0028 (9)0.0023 (9)0.0138 (9)
C110.0324 (11)0.0188 (10)0.0273 (12)0.0037 (9)0.0011 (9)0.0071 (9)
C120.0201 (10)0.0267 (11)0.0217 (11)0.0026 (9)0.0002 (9)0.0058 (9)
C130.0260 (11)0.0301 (12)0.0298 (12)0.0037 (9)0.0054 (9)0.0161 (10)
C140.0254 (11)0.0216 (11)0.0334 (12)0.0057 (9)0.0044 (9)0.0142 (9)
C150.0224 (11)0.0397 (14)0.0365 (14)0.0011 (10)0.0039 (10)0.0101 (11)
C160.0285 (11)0.0393 (13)0.0312 (13)0.0131 (10)0.0039 (10)0.0170 (11)
Geometric parameters (Å, º) top
Br1—C121.899 (2)C7—C81.388 (3)
O1—C11.238 (2)C7—H70.9500
N1—C11.360 (3)C9—C101.386 (3)
N1—C91.443 (2)C9—C141.386 (3)
N1—C21.502 (2)C10—C111.384 (3)
N2—C31.361 (3)C10—H100.9500
N2—C21.459 (3)C11—C121.386 (3)
N2—H20.75 (2)C11—H110.9500
C1—C81.478 (3)C12—C131.378 (3)
C2—C151.508 (3)C13—C141.386 (3)
C2—C161.529 (3)C13—H130.9500
C3—C81.404 (3)C14—H140.9500
C3—C41.404 (3)C15—H15A0.9800
C4—C51.372 (3)C15—H15B0.9800
C4—H40.9500C15—H15C0.9800
C5—C61.391 (3)C16—H16A0.9800
C5—H50.9500C16—H16B0.9800
C6—C71.376 (3)C16—H16C0.9800
C6—H60.9500
C1—N1—C9117.44 (15)C3—C8—C1118.95 (18)
C1—N1—C2122.19 (15)C10—C9—C14119.94 (18)
C9—N1—C2118.55 (16)C10—C9—N1119.61 (17)
C3—N2—C2120.15 (17)C14—C9—N1120.44 (17)
C3—N2—H2115.3 (19)C11—C10—C9120.26 (18)
C2—N2—H2111.2 (19)C11—C10—H10119.9
O1—C1—N1121.48 (18)C9—C10—H10119.9
O1—C1—C8121.87 (18)C10—C11—C12118.95 (19)
N1—C1—C8116.55 (16)C10—C11—H11120.5
N2—C2—N1106.34 (16)C12—C11—H11120.5
N2—C2—C15107.53 (17)C13—C12—C11121.61 (19)
N1—C2—C15110.81 (16)C13—C12—Br1119.58 (16)
N2—C2—C16111.52 (17)C11—C12—Br1118.78 (15)
N1—C2—C16109.40 (16)C12—C13—C14118.92 (19)
C15—C2—C16111.12 (19)C12—C13—H13120.5
N2—C3—C8119.28 (18)C14—C13—H13120.5
N2—C3—C4122.48 (19)C13—C14—C9120.32 (19)
C8—C3—C4118.1 (2)C13—C14—H14119.8
C5—C4—C3120.4 (2)C9—C14—H14119.8
C5—C4—H4119.8C2—C15—H15A109.5
C3—C4—H4119.8C2—C15—H15B109.5
C4—C5—C6121.5 (2)H15A—C15—H15B109.5
C4—C5—H5119.3C2—C15—H15C109.5
C6—C5—H5119.3H15A—C15—H15C109.5
C7—C6—C5118.6 (2)H15B—C15—H15C109.5
C7—C6—H6120.7C2—C16—H16A109.5
C5—C6—H6120.7C2—C16—H16B109.5
C6—C7—C8121.11 (19)H16A—C16—H16B109.5
C6—C7—H7119.4C2—C16—H16C109.5
C8—C7—H7119.4H16A—C16—H16C109.5
C7—C8—C3120.33 (18)H16B—C16—H16C109.5
C7—C8—C1120.44 (17)
C9—N1—C1—O13.9 (3)N2—C3—C8—C7176.89 (18)
C2—N1—C1—O1168.31 (18)C4—C3—C8—C71.4 (3)
C9—N1—C1—C8179.59 (16)N2—C3—C8—C13.0 (3)
C2—N1—C1—C815.2 (3)C4—C3—C8—C1172.51 (18)
C3—N2—C2—N146.0 (2)O1—C1—C8—C76.1 (3)
C3—N2—C2—C15164.70 (18)N1—C1—C8—C7177.48 (17)
C3—N2—C2—C1673.2 (2)O1—C1—C8—C3167.82 (19)
C1—N1—C2—N240.1 (2)N1—C1—C8—C38.6 (3)
C9—N1—C2—N2155.65 (16)C1—N1—C9—C10100.2 (2)
C1—N1—C2—C15156.71 (18)C2—N1—C9—C1094.9 (2)
C9—N1—C2—C1539.1 (2)C1—N1—C9—C1478.7 (2)
C1—N1—C2—C1680.4 (2)C2—N1—C9—C1486.2 (2)
C9—N1—C2—C1683.8 (2)C14—C9—C10—C110.1 (3)
C2—N2—C3—C827.3 (3)N1—C9—C10—C11179.04 (19)
C2—N2—C3—C4157.40 (19)C9—C10—C11—C120.0 (3)
N2—C3—C4—C5176.6 (2)C10—C11—C12—C130.4 (3)
C8—C3—C4—C51.3 (3)C10—C11—C12—Br1177.58 (16)
C3—C4—C5—C60.3 (3)C11—C12—C13—C141.0 (3)
C4—C5—C6—C70.6 (3)Br1—C12—C13—C14176.97 (16)
C5—C6—C7—C80.5 (3)C12—C13—C14—C91.2 (3)
C6—C7—C8—C30.5 (3)C10—C9—C14—C130.7 (3)
C6—C7—C8—C1173.26 (18)N1—C9—C14—C13179.64 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16B···Br1i0.983.023.894 (2)149
N2—H2···O1ii0.75 (2)2.18 (3)2.925 (2)173 (2)
Symmetry codes: (i) x, y, z+2; (ii) x+1, y, z.
 

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