The title compound, C
14H
10Cl
2N
2O·0.5C
3H
6O, was synthesized by the reaction of 5-chloro-
N-(4-chlorophenyl)-2-nitrobenzylamine with triphosgene, induced by a low-valent titanium reagent (TiCl
4/Zn). The dihydroquinazoline ring exhibits a boat conformation. N—H
O hydrogen bonds form centrosymmetric dimers. There are also some weak C—H
O interactions.
Supporting information
CCDC reference: 259849
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.047
- wR factor = 0.112
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.25 Ratio
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C102
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 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
Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: SHELXL97.
6-Chloro-3-(4-chlorophenyl)-3,4-dihydroquinazolin-2(1
H)-one–acetone
(2/1)
top
Crystal data top
C14H10Cl2N2O·0.5C3H6O | F(000) = 664 |
Mr = 322.18 | Dx = 1.479 Mg m−3 |
Monoclinic, P21/n | Melting point: 589 K |
Hall symbol: -p 2yn | Mo Kα radiation, λ = 0.71070 Å |
a = 5.8060 (18) Å | Cell parameters from 6413 reflections |
b = 13.250 (4) Å | θ = 3.1–27.5° |
c = 18.810 (6) Å | µ = 0.45 mm−1 |
β = 90.802 (7)° | T = 193 K |
V = 1447.0 (8) Å3 | Block, colorless |
Z = 4 | 0.65 × 0.35 × 0.30 mm |
Data collection top
Rigaku Mercury diffractometer | 3315 independent reflections |
Radiation source: fine-focus sealed tube | 3067 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −6→7 |
Absorption correction: multi-scan Jacobson (1998) | k = −15→17 |
Tmin = 0.759, Tmax = 0.877 | l = −24→24 |
15816 measured reflections | |
Refinement top
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0428P)2 + 0.7556P] where P = (Fo2 + 2Fc2)/3 |
3315 reflections | (Δ/σ)max = 0.007 |
210 parameters | Δρmax = 0.32 e Å−3 |
1 restraint | Δρmin = −0.26 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.89692 (9) | 0.66859 (4) | 0.32782 (3) | 0.05129 (17) | |
Cl2 | 0.35496 (10) | 1.50946 (4) | 0.27084 (3) | 0.05144 (17) | |
O1 | 0.0875 (2) | 1.11590 (10) | 0.45565 (7) | 0.0377 (3) | |
N1 | 0.2461 (3) | 0.96108 (12) | 0.44897 (8) | 0.0376 (4) | |
H1 | 0.1498 | 0.9395 | 0.4798 | 0.045* | |
N2 | 0.4058 (2) | 1.09496 (11) | 0.38771 (8) | 0.0316 (3) | |
C1 | 0.2395 (3) | 1.06046 (14) | 0.43213 (9) | 0.0315 (4) | |
C2 | 0.6106 (3) | 1.03705 (14) | 0.36741 (10) | 0.0364 (4) | |
H2A | 0.7425 | 1.0609 | 0.3948 | 0.044* | |
H2B | 0.6413 | 1.0488 | 0.3175 | 0.044* | |
C3 | 0.5816 (3) | 0.92575 (14) | 0.37961 (9) | 0.0309 (4) | |
C4 | 0.3983 (3) | 0.89106 (14) | 0.41978 (9) | 0.0323 (4) | |
C5 | 0.7357 (3) | 0.85633 (15) | 0.35198 (9) | 0.0345 (4) | |
H5 | 0.8603 | 0.8783 | 0.3256 | 0.041* | |
C6 | 0.7032 (3) | 0.75488 (15) | 0.36379 (10) | 0.0366 (4) | |
C7 | 0.5197 (3) | 0.71979 (15) | 0.40289 (11) | 0.0413 (4) | |
H7 | 0.4993 | 0.6509 | 0.4101 | 0.050* | |
C8 | 0.3671 (3) | 0.78856 (15) | 0.43107 (10) | 0.0392 (4) | |
H8 | 0.2434 | 0.7661 | 0.4576 | 0.047* | |
C9 | 0.3908 (3) | 1.19607 (14) | 0.36186 (9) | 0.0303 (4) | |
C10 | 0.5754 (3) | 1.26155 (15) | 0.37142 (10) | 0.0369 (4) | |
H10 | 0.7057 | 1.2406 | 0.3966 | 0.044* | |
C11 | 0.5651 (3) | 1.35831 (15) | 0.34331 (11) | 0.0404 (4) | |
H11 | 0.6880 | 1.4026 | 0.3496 | 0.048* | |
C12 | 0.3704 (3) | 1.38790 (14) | 0.30596 (10) | 0.0362 (4) | |
C13 | 0.1867 (3) | 1.32322 (15) | 0.29546 (10) | 0.0378 (4) | |
H13 | 0.0574 | 1.3441 | 0.2697 | 0.045* | |
C14 | 0.1973 (3) | 1.22740 (14) | 0.32368 (10) | 0.0347 (4) | |
H14 | 0.0741 | 1.1834 | 0.3171 | 0.042* | |
C101 | 0.558 (4) | 1.1024 (15) | −0.0283 (11) | 0.122 (6) | 0.50 |
H10A | 0.4704 | 1.1396 | 0.0057 | 0.184* | 0.50 |
H10B | 0.4747 | 1.0997 | −0.0727 | 0.184* | 0.50 |
H10C | 0.7036 | 1.1351 | −0.0352 | 0.184* | 0.50 |
C102 | 0.5976 (13) | 0.9978 (7) | −0.0016 (4) | 0.077 (2) | 0.50 |
C103 | 0.408 (4) | 0.9397 (13) | 0.0200 (10) | 0.122 (6) | 0.50 |
H10D | 0.4595 | 0.8729 | 0.0323 | 0.183* | 0.50 |
H10E | 0.2972 | 0.9357 | −0.0182 | 0.183* | 0.50 |
H10F | 0.3388 | 0.9706 | 0.0605 | 0.183* | 0.50 |
O104 | 0.7887 (12) | 0.9640 (6) | 0.0028 (4) | 0.149 (3) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0480 (3) | 0.0499 (3) | 0.0563 (3) | 0.0091 (2) | 0.0126 (2) | −0.0080 (2) |
Cl2 | 0.0585 (3) | 0.0352 (3) | 0.0609 (3) | 0.0067 (2) | 0.0109 (3) | 0.0074 (2) |
O1 | 0.0314 (7) | 0.0418 (7) | 0.0403 (7) | −0.0010 (6) | 0.0143 (6) | 0.0016 (6) |
N1 | 0.0333 (8) | 0.0400 (9) | 0.0402 (8) | −0.0016 (7) | 0.0189 (7) | 0.0054 (7) |
N2 | 0.0260 (7) | 0.0360 (8) | 0.0332 (7) | −0.0009 (6) | 0.0094 (6) | 0.0047 (6) |
C1 | 0.0260 (8) | 0.0387 (9) | 0.0301 (8) | −0.0046 (7) | 0.0061 (7) | 0.0012 (7) |
C2 | 0.0266 (8) | 0.0423 (10) | 0.0406 (10) | 0.0000 (8) | 0.0103 (7) | 0.0080 (8) |
C3 | 0.0269 (8) | 0.0404 (10) | 0.0254 (8) | −0.0014 (7) | 0.0028 (6) | 0.0043 (7) |
C4 | 0.0289 (8) | 0.0392 (10) | 0.0289 (8) | −0.0008 (7) | 0.0062 (7) | 0.0020 (7) |
C5 | 0.0278 (8) | 0.0469 (11) | 0.0289 (8) | 0.0012 (8) | 0.0058 (7) | 0.0033 (7) |
C6 | 0.0344 (9) | 0.0422 (10) | 0.0332 (9) | 0.0045 (8) | 0.0020 (7) | −0.0028 (8) |
C7 | 0.0436 (11) | 0.0365 (10) | 0.0440 (11) | −0.0028 (8) | 0.0053 (9) | 0.0011 (8) |
C8 | 0.0349 (9) | 0.0431 (11) | 0.0399 (10) | −0.0063 (8) | 0.0121 (8) | 0.0021 (8) |
C9 | 0.0274 (8) | 0.0355 (9) | 0.0283 (8) | −0.0012 (7) | 0.0085 (7) | 0.0014 (7) |
C10 | 0.0298 (9) | 0.0430 (10) | 0.0380 (10) | −0.0050 (8) | 0.0012 (7) | 0.0041 (8) |
C11 | 0.0353 (10) | 0.0396 (10) | 0.0464 (11) | −0.0078 (8) | 0.0047 (8) | 0.0010 (8) |
C12 | 0.0398 (10) | 0.0330 (9) | 0.0361 (9) | 0.0026 (8) | 0.0119 (8) | −0.0001 (7) |
C13 | 0.0332 (9) | 0.0413 (10) | 0.0388 (10) | 0.0068 (8) | 0.0018 (8) | −0.0011 (8) |
C14 | 0.0291 (9) | 0.0385 (10) | 0.0365 (9) | −0.0022 (7) | 0.0028 (7) | −0.0032 (8) |
C101 | 0.113 (10) | 0.195 (13) | 0.059 (5) | −0.061 (10) | −0.020 (5) | 0.057 (9) |
C102 | 0.069 (4) | 0.112 (6) | 0.049 (4) | 0.023 (5) | −0.003 (3) | −0.022 (4) |
C103 | 0.125 (12) | 0.175 (19) | 0.065 (9) | −0.014 (12) | 0.007 (7) | 0.045 (9) |
O104 | 0.123 (5) | 0.182 (7) | 0.141 (6) | 0.077 (5) | 0.003 (4) | 0.000 (5) |
Geometric parameters (Å, º) top
Cl1—C6 | 1.7466 (19) | C8—H8 | 0.9300 |
Cl2—C12 | 1.743 (2) | C9—C10 | 1.388 (3) |
O1—C1 | 1.235 (2) | C9—C14 | 1.389 (3) |
N1—C1 | 1.355 (2) | C10—C11 | 1.388 (3) |
N1—C4 | 1.399 (2) | C10—H10 | 0.9300 |
N1—H1 | 0.8600 | C11—C12 | 1.380 (3) |
N2—C1 | 1.364 (2) | C11—H11 | 0.9300 |
N2—C9 | 1.427 (2) | C12—C13 | 1.380 (3) |
N2—C2 | 1.470 (2) | C13—C14 | 1.377 (3) |
C2—C3 | 1.502 (3) | C13—H13 | 0.9300 |
C2—H2A | 0.9700 | C14—H14 | 0.9300 |
C2—H2B | 0.9700 | C101—C102 | 1.490 (18) |
C3—C5 | 1.389 (3) | C101—H10A | 0.9600 |
C3—C4 | 1.392 (2) | C101—H10B | 0.9600 |
C4—C8 | 1.387 (3) | C101—H10C | 0.9600 |
C5—C6 | 1.376 (3) | C102—O104 | 1.198 (9) |
C5—H5 | 0.9300 | C102—C103 | 1.41 (2) |
C6—C7 | 1.384 (3) | C103—H10D | 0.9600 |
C7—C8 | 1.381 (3) | C103—H10E | 0.9600 |
C7—H7 | 0.9300 | C103—H10F | 0.9600 |
| | | |
C1—N1—C4 | 124.65 (15) | C8—C7—C6 | 119.01 (18) |
C1—N1—H1 | 117.7 | C8—C7—H7 | 120.5 |
C4—N1—H1 | 117.7 | C6—C7—H7 | 120.5 |
C1—N2—C9 | 118.88 (15) | C7—C8—C4 | 120.09 (17) |
C1—N2—C2 | 124.47 (15) | C7—C8—H8 | 120.0 |
C9—N2—C2 | 116.54 (14) | C4—C8—H8 | 120.0 |
O1—C1—N1 | 120.81 (15) | C10—C9—C14 | 119.84 (17) |
O1—C1—N2 | 122.37 (17) | C10—C9—N2 | 119.95 (16) |
N1—C1—N2 | 116.82 (16) | C14—C9—N2 | 120.11 (16) |
N2—C2—C3 | 112.34 (14) | C11—C10—C9 | 119.94 (18) |
N2—C2—H2A | 109.1 | C11—C10—H10 | 120.0 |
C3—C2—H2A | 109.1 | C9—C10—H10 | 120.0 |
N2—C2—H2B | 109.1 | C12—C11—C10 | 119.13 (18) |
C3—C2—H2B | 109.1 | C12—C11—H11 | 120.4 |
H2A—C2—H2B | 107.9 | C10—C11—H11 | 120.4 |
C5—C3—C4 | 119.06 (17) | C11—C12—C13 | 121.51 (18) |
C5—C3—C2 | 121.26 (16) | C11—C12—Cl2 | 119.53 (15) |
C4—C3—C2 | 119.68 (16) | C13—C12—Cl2 | 118.95 (15) |
C8—C4—C3 | 120.60 (17) | C14—C13—C12 | 119.13 (18) |
C8—C4—N1 | 120.31 (16) | C14—C13—H13 | 120.4 |
C3—C4—N1 | 119.09 (16) | C12—C13—H13 | 120.4 |
C6—C5—C3 | 119.74 (17) | C13—C14—C9 | 120.44 (17) |
C6—C5—H5 | 120.1 | C13—C14—H14 | 119.8 |
C3—C5—H5 | 120.1 | C9—C14—H14 | 119.8 |
C5—C6—C7 | 121.49 (18) | O104—C102—C103 | 120.1 (13) |
C5—C6—Cl1 | 119.11 (15) | O104—C102—C101 | 120.6 (13) |
C7—C6—Cl1 | 119.40 (16) | C103—C102—C101 | 119.3 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 1.99 | 2.847 (2) | 175 |
C2—H2A···O1ii | 0.97 | 2.41 | 3.374 (2) | 176 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x+1, y, z. |