6-Chloro-3-(p-tolyl)-3,4-di­hydro­quinazolin-2(1H)-one

The title compound, C₁₅H₁₃ClN₂O, was synthesized by the reaction of 5-chloro-N-(p-tolyl)-2-nitro­benzyl­amine with triphosgene, induced by a low-valent titanium reagent (TiCl₄/Zn). The di­hydro­pyrimidine ring adopts a boat conformation.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.065
• wR factor = 0.169
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors  for         C2

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N2
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  Cl1     ..       3.43 Ang.

   0 ALERT level A = In general: serious problem
   1 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
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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.

6-chloro-3-(4-methylphenyl)-3,4-dihydroquinazolin-2(1H)-one

Crystal data

C15H13ClN2O	F(000) = 1136
Mr = 272.72	Dx = 1.358 Mg m^−3
Monoclinic, C2/c	Melting point = 487–488 K
Hall symbol: -c 2yc	Mo Kα radiation, λ = 0.71070 Å
a = 19.006 (6) Å	Cell parameters from 5465 reflections
b = 12.836 (3) Å	θ = 3.3–27.5°
c = 11.484 (4) Å	µ = 0.28 mm^−1
β = 107.764 (7)°	T = 193 K
V = 2668.1 (13) Å^3	Block, colorless
Z = 8	0.80 × 0.52 × 0.41 mm

Data collection

Rigaku Mercury diffractometer	3048 independent reflections
Radiation source: fine-focus sealed tube	2786 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 7.31 pixels mm^-1	θmax = 27.5°, θmin = 3.7°
ω scans	h = −24→24
Absorption correction: multi-scan (Jacobson, 1998)	k = −16→14
Tmin = 0.808, Tmax = 0.894	l = −14→12
14355 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0745P)^2 + 3.41P] where P = (Fo^2 + 2Fc^2)/3
3048 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.06459 (4)	0.50104 (6)	0.92336 (7)	0.0686 (3)
O1	0.30906 (8)	0.64026 (11)	0.49356 (14)	0.0443 (4)
N1	0.23341 (12)	0.66181 (15)	0.60960 (19)	0.0510 (5)
N2	0.29200 (10)	0.50357 (12)	0.60830 (16)	0.0393 (4)
C1	0.27980 (12)	0.60371 (15)	0.56696 (18)	0.0393 (4)
C2	0.2646 (2)	0.4590 (2)	0.7013 (3)	0.0929 (13)
H2A	0.3060	0.4528	0.7782	0.111*
H2B	0.2460	0.3879	0.6759	0.111*
C3	0.20393 (14)	0.52170 (16)	0.7257 (2)	0.0465 (5)
C4	0.19219 (12)	0.62397 (15)	0.68232 (18)	0.0389 (4)
C5	0.16274 (13)	0.48371 (17)	0.79741 (19)	0.0437 (5)
H5	0.1684	0.4134	0.8246	0.052*
C6	0.11359 (11)	0.54813 (18)	0.82912 (19)	0.0437 (5)
C7	0.10279 (12)	0.65033 (18)	0.7885 (2)	0.0443 (5)
H7	0.0691	0.6941	0.8118	0.053*
C8	0.14182 (11)	0.68760 (16)	0.71339 (18)	0.0389 (4)
H8	0.1341	0.7569	0.6831	0.047*
C9	0.34149 (11)	0.44097 (15)	0.56518 (18)	0.0391 (4)
C10	0.41670 (13)	0.45703 (19)	0.6083 (2)	0.0548 (6)
H10	0.4363	0.5083	0.6693	0.066*
C11	0.46379 (14)	0.3986 (2)	0.5629 (3)	0.0629 (7)
H11	0.5155	0.4103	0.5937	0.076*
C12	0.43735 (14)	0.3241 (2)	0.4742 (2)	0.0549 (6)
C13	0.36183 (14)	0.3078 (2)	0.4336 (2)	0.0549 (6)
H13	0.3422	0.2565	0.3728	0.066*
C14	0.31386 (12)	0.36436 (17)	0.4794 (2)	0.0454 (5)
H14	0.2623	0.3503	0.4518	0.054*
C15	0.48889 (19)	0.2615 (3)	0.4238 (3)	0.0838 (10)
H15A	0.5317	0.3042	0.4243	0.126*
H15B	0.4628	0.2400	0.3398	0.126*
H15C	0.5056	0.1995	0.4746	0.126*
H1	0.2222 (14)	0.719 (2)	0.578 (2)	0.052 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0593 (4)	0.0835 (5)	0.0764 (5)	0.0001 (3)	0.0407 (4)	0.0272 (3)
O1	0.0573 (9)	0.0341 (7)	0.0513 (9)	0.0022 (6)	0.0310 (7)	0.0084 (6)
N1	0.0798 (14)	0.0292 (9)	0.0608 (12)	0.0100 (9)	0.0462 (11)	0.0123 (8)
N2	0.0515 (10)	0.0309 (8)	0.0407 (9)	0.0051 (7)	0.0220 (8)	0.0074 (6)
C1	0.0535 (12)	0.0297 (9)	0.0394 (10)	0.0015 (8)	0.0210 (9)	0.0045 (8)
C2	0.162 (3)	0.0496 (15)	0.114 (3)	0.0405 (18)	0.113 (3)	0.0388 (16)
C3	0.0689 (15)	0.0340 (10)	0.0461 (12)	0.0016 (10)	0.0316 (11)	0.0057 (8)
C4	0.0524 (11)	0.0331 (10)	0.0362 (10)	−0.0033 (8)	0.0211 (9)	0.0011 (7)
C5	0.0558 (13)	0.0382 (10)	0.0392 (10)	−0.0075 (9)	0.0177 (9)	0.0048 (8)
C6	0.0378 (10)	0.0562 (13)	0.0387 (10)	−0.0095 (9)	0.0140 (8)	0.0047 (9)
C7	0.0384 (10)	0.0525 (12)	0.0439 (11)	−0.0001 (9)	0.0154 (8)	0.0011 (9)
C8	0.0425 (10)	0.0357 (10)	0.0379 (10)	−0.0024 (8)	0.0116 (8)	0.0001 (8)
C9	0.0488 (11)	0.0340 (9)	0.0381 (10)	0.0060 (8)	0.0186 (8)	0.0082 (8)
C10	0.0493 (13)	0.0481 (13)	0.0656 (15)	−0.0024 (10)	0.0156 (11)	−0.0056 (11)
C11	0.0444 (13)	0.0610 (15)	0.0865 (19)	0.0033 (11)	0.0245 (12)	0.0026 (14)
C12	0.0601 (14)	0.0537 (14)	0.0596 (14)	0.0166 (11)	0.0310 (12)	0.0127 (11)
C13	0.0652 (15)	0.0521 (13)	0.0465 (12)	0.0129 (11)	0.0161 (11)	−0.0039 (10)
C14	0.0445 (11)	0.0450 (11)	0.0445 (11)	0.0061 (9)	0.0105 (9)	−0.0006 (9)
C15	0.086 (2)	0.085 (2)	0.098 (2)	0.0300 (18)	0.0538 (19)	0.0052 (18)

Geometric parameters (Å, º)

Cl1—C6	1.737 (2)	C7—C8	1.383 (3)
O1—C1	1.235 (2)	C7—H7	0.9500
N1—C1	1.355 (3)	C8—H8	0.9500
N1—C4	1.395 (3)	C9—C14	1.377 (3)
N1—H1	0.82 (3)	C9—C10	1.378 (3)
N2—C1	1.365 (2)	C10—C11	1.385 (4)
N2—C9	1.435 (3)	C10—H10	0.9500
N2—C2	1.442 (3)	C11—C12	1.376 (4)
C2—C3	1.500 (4)	C11—H11	0.9500
C2—H2A	0.9900	C12—C13	1.383 (4)
C2—H2B	0.9900	C12—C15	1.512 (4)
C3—C5	1.387 (3)	C13—C14	1.388 (3)
C3—C4	1.398 (3)	C13—H13	0.9500
C4—C8	1.385 (3)	C14—H14	0.9500
C5—C6	1.377 (3)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C6—C7	1.387 (3)	C15—H15C	0.9800
C1—N1—C4	124.80 (18)	C6—C7—H7	120.5
C1—N1—H1	116.6 (18)	C7—C8—C4	120.05 (19)
C4—N1—H1	117.2 (18)	C7—C8—H8	120.0
C1—N2—C9	117.82 (16)	C4—C8—H8	120.0
C1—N2—C2	124.71 (18)	C14—C9—C10	119.4 (2)
C9—N2—C2	117.17 (17)	C14—C9—N2	119.96 (19)
O1—C1—N1	121.03 (18)	C10—C9—N2	120.6 (2)
O1—C1—N2	122.06 (19)	C9—C10—C11	120.1 (2)
N1—C1—N2	116.91 (18)	C9—C10—H10	119.9
N2—C2—C3	113.4 (2)	C11—C10—H10	119.9
N2—C2—H2A	108.9	C12—C11—C10	121.5 (2)
C3—C2—H2A	108.9	C12—C11—H11	119.2
N2—C2—H2B	108.9	C10—C11—H11	119.2
C3—C2—H2B	108.9	C11—C12—C13	117.5 (2)
H2A—C2—H2B	107.7	C11—C12—C15	121.3 (3)
C5—C3—C4	119.0 (2)	C13—C12—C15	121.2 (3)
C5—C3—C2	121.8 (2)	C12—C13—C14	121.8 (2)
C4—C3—C2	119.0 (2)	C12—C13—H13	119.1
C8—C4—N1	120.48 (18)	C14—C13—H13	119.1
C8—C4—C3	120.65 (19)	C9—C14—C13	119.5 (2)
N1—C4—C3	118.85 (19)	C9—C14—H14	120.2
C6—C5—C3	119.8 (2)	C13—C14—H14	120.2
C6—C5—H5	120.1	C12—C15—H15A	109.5
C3—C5—H5	120.1	C12—C15—H15B	109.5
C5—C6—C7	121.45 (19)	H15A—C15—H15B	109.5
C5—C6—Cl1	119.44 (17)	C12—C15—H15C	109.5
C7—C6—Cl1	119.11 (17)	H15A—C15—H15C	109.5
C8—C7—C6	119.0 (2)	H15B—C15—H15C	109.5
C8—C7—H7	120.5
C4—N1—C1—O1	173.0 (2)	C5—C6—C7—C8	0.7 (3)
C4—N1—C1—N2	−6.6 (3)	Cl1—C6—C7—C8	−179.95 (16)
C9—N2—C1—O1	1.0 (3)	C6—C7—C8—C4	−1.6 (3)
C2—N2—C1—O1	174.6 (3)	N1—C4—C8—C7	−178.1 (2)
C9—N2—C1—N1	−179.4 (2)	C3—C4—C8—C7	0.3 (3)
C2—N2—C1—N1	−5.9 (4)	C1—N2—C9—C14	−105.4 (2)
C1—N2—C2—C3	16.1 (5)	C2—N2—C9—C14	80.6 (3)
C9—N2—C2—C3	−170.3 (2)	C1—N2—C9—C10	74.3 (3)
N2—C2—C3—C5	169.7 (3)	C2—N2—C9—C10	−99.8 (3)
N2—C2—C3—C4	−15.1 (5)	C14—C9—C10—C11	1.9 (4)
C1—N1—C4—C8	−174.9 (2)	N2—C9—C10—C11	−177.7 (2)
C1—N1—C4—C3	6.7 (4)	C9—C10—C11—C12	0.3 (4)
C5—C3—C4—C8	1.9 (3)	C10—C11—C12—C13	−1.4 (4)
C2—C3—C4—C8	−173.5 (3)	C10—C11—C12—C15	179.2 (3)
C5—C3—C4—N1	−179.6 (2)	C11—C12—C13—C14	0.3 (4)
C2—C3—C4—N1	5.0 (4)	C15—C12—C13—C14	179.7 (2)
C4—C3—C5—C6	−2.8 (4)	C10—C9—C14—C13	−2.9 (3)
C2—C3—C5—C6	172.4 (3)	N2—C9—C14—C13	176.72 (19)
C3—C5—C6—C7	1.6 (3)	C12—C13—C14—C9	1.8 (4)
C3—C5—C6—Cl1	−177.80 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.82 (3)	2.00 (3)	2.815 (2)	177 (3)

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.