8-Chloro-5,5-dimethyl-5,6-dihydro-tetra-zolo[1,5-c]quinazoline.

In the title compound, C(10)H(10)ClN(5), the tetra-zole ring and the phenyl ring make a dihedral angle of 7.7 (2)°. The hexa-hydro-pyrimidine ring adopts a screw-boat conformation. In the crystal, inter-molecular bifurcated N-H⋯(N,N) hydrogen bonds link the mol-ecules into [001] chains.

Related literature

For applications of tetra­zole derivatives, see: Upadhayaya et al. (2004 ▶); Poonian et al. (1976 ▶); Ismail et al. (2006 ▶); Mulwad & Kewat (2008 ▶); Uchida et al. (1989 ▶). For ring conformations, see: Boeyens (1978 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H10ClN5

M = 235.68

Monoclinic,

a = 6.8324 (16) Å

b = 21.532 (5) Å

c = 9.4337 (16) Å

β = 130.823 (11)°

V = 1050.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 100 K

0.16 × 0.11 × 0.05 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.948, T max = 0.982

9660 measured reflections

2412 independent reflections

1777 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.137

S = 1.12

2412 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004688X/hb5733sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004688X/hb5733Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H10ClN5	F(000) = 488
Mr = 235.68	Dx = 1.491 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1888 reflections
a = 6.8324 (16) Å	θ = 3.0–29.9°
b = 21.532 (5) Å	µ = 0.34 mm−1
c = 9.4337 (16) Å	T = 100 K
β = 130.823 (11)°	Plate, colourless
V = 1050.2 (4) Å3	0.16 × 0.11 × 0.05 mm
Z = 4

Bruker APEXII DUO CCD diffractometer	2412 independent reflections
Radiation source: fine-focus sealed tube	1777 reflections with I > 2σ(I)
graphite	Rint = 0.066
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.948, Tmax = 0.982	k = −27→27
9660 measured reflections	l = −12→12

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0361P)2 + 1.9098P] where P = (Fo2 + 2Fc2)/3
2412 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
Cl1	0.68351 (15)	0.62515 (4)	0.46138 (11)	0.0285 (2)
N1	0.0252 (5)	0.85800 (13)	−0.2050 (3)	0.0225 (6)
N2	0.0079 (5)	0.92121 (14)	−0.2261 (3)	0.0276 (6)
N3	0.1672 (5)	0.94937 (13)	−0.0661 (3)	0.0248 (6)
N4	0.2938 (4)	0.90385 (12)	0.0634 (3)	0.0192 (5)
N5	0.6368 (5)	0.85848 (12)	0.3484 (3)	0.0210 (6)
C1	0.2056 (5)	0.84885 (14)	−0.0218 (4)	0.0190 (6)
C2	0.3106 (5)	0.79248 (14)	0.0880 (4)	0.0185 (6)
C3	0.2129 (6)	0.73316 (15)	0.0145 (4)	0.0216 (7)
H3A	0.0704	0.7285	−0.1122	0.026*
C4	0.3259 (6)	0.68153 (15)	0.1280 (4)	0.0234 (7)
H4A	0.2613	0.6420	0.0797	0.028*
C5	0.5397 (6)	0.69013 (15)	0.3174 (4)	0.0213 (6)
C6	0.6402 (6)	0.74777 (15)	0.3947 (4)	0.0209 (6)
H6A	0.7816	0.7518	0.5218	0.025*
C7	0.5276 (5)	0.80012 (14)	0.2800 (4)	0.0176 (6)
C8	0.4845 (5)	0.91539 (14)	0.2689 (4)	0.0189 (6)
C9	0.6573 (6)	0.96910 (15)	0.3100 (4)	0.0271 (7)
H9A	0.7358	0.9608	0.2569	0.041*
H9B	0.7896	0.9742	0.4431	0.041*
H9C	0.5561	1.0064	0.2561	0.041*
C10	0.3352 (6)	0.92761 (16)	0.3348 (4)	0.0254 (7)
H10A	0.2294	0.8923	0.3065	0.038*
H10B	0.2275	0.9635	0.2718	0.038*
H10C	0.4549	0.9347	0.4675	0.038*
H1N5	0.751 (8)	0.8595 (18)	0.467 (6)	0.039 (11)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0280 (4)	0.0248 (4)	0.0334 (4)	0.0052 (3)	0.0204 (3)	0.0085 (4)
N1	0.0187 (12)	0.0307 (16)	0.0131 (12)	0.0000 (10)	0.0082 (10)	0.0003 (11)
N2	0.0240 (13)	0.0355 (17)	0.0148 (12)	0.0021 (12)	0.0089 (11)	0.0035 (12)
N3	0.0251 (13)	0.0289 (15)	0.0147 (12)	0.0052 (11)	0.0106 (11)	0.0061 (11)
N4	0.0191 (12)	0.0225 (14)	0.0107 (11)	0.0023 (10)	0.0074 (10)	0.0021 (10)
N5	0.0173 (12)	0.0213 (14)	0.0104 (12)	−0.0010 (10)	0.0029 (10)	−0.0017 (10)
C1	0.0154 (13)	0.0267 (16)	0.0135 (13)	−0.0013 (12)	0.0088 (11)	−0.0040 (12)
C2	0.0167 (13)	0.0237 (17)	0.0151 (13)	0.0009 (12)	0.0104 (11)	−0.0009 (12)
C3	0.0182 (14)	0.0282 (18)	0.0166 (14)	−0.0047 (12)	0.0105 (12)	−0.0053 (13)
C4	0.0237 (15)	0.0227 (17)	0.0253 (16)	−0.0048 (13)	0.0166 (13)	−0.0063 (13)
C5	0.0214 (14)	0.0236 (17)	0.0257 (15)	0.0044 (12)	0.0184 (13)	0.0044 (13)
C6	0.0178 (14)	0.0259 (17)	0.0165 (14)	0.0015 (12)	0.0101 (12)	0.0001 (12)
C7	0.0162 (13)	0.0204 (16)	0.0171 (13)	−0.0006 (11)	0.0113 (11)	−0.0016 (12)
C8	0.0174 (13)	0.0207 (16)	0.0135 (13)	−0.0005 (12)	0.0079 (11)	0.0006 (12)
C9	0.0288 (16)	0.0279 (18)	0.0178 (14)	−0.0080 (14)	0.0122 (13)	−0.0009 (13)
C10	0.0240 (15)	0.0300 (19)	0.0195 (15)	0.0002 (13)	0.0130 (13)	−0.0006 (13)

Cl1—C5	1.739 (3)	C3—H3A	0.9300
N1—C1	1.326 (4)	C4—C5	1.396 (4)
N1—N2	1.369 (4)	C4—H4A	0.9300
N2—N3	1.297 (4)	C5—C6	1.374 (4)
N3—N4	1.349 (3)	C6—C7	1.394 (4)
N4—C1	1.334 (4)	C6—H6A	0.9300
N4—C8	1.489 (3)	C8—C9	1.511 (4)
N5—C7	1.386 (4)	C8—C10	1.525 (4)
N5—C8	1.458 (4)	C9—H9A	0.9600
N5—H1N5	0.85 (4)	C9—H9B	0.9600
C1—C2	1.445 (4)	C9—H9C	0.9600
C2—C3	1.397 (4)	C10—H10A	0.9600
C2—C7	1.413 (4)	C10—H10B	0.9600
C3—C4	1.378 (4)	C10—H10C	0.9600
C1—N1—N2	104.8 (2)	C5—C6—C7	119.2 (3)
N3—N2—N1	111.6 (2)	C5—C6—H6A	120.4
N2—N3—N4	105.5 (3)	C7—C6—H6A	120.4
C1—N4—N3	109.3 (2)	N5—C7—C6	121.0 (3)
C1—N4—C8	126.8 (2)	N5—C7—C2	119.8 (3)
N3—N4—C8	123.7 (2)	C6—C7—C2	119.0 (3)
C7—N5—C8	122.4 (2)	N5—C8—N4	104.6 (2)
C7—N5—H1N5	113 (3)	N5—C8—C9	109.6 (2)
C8—N5—H1N5	113 (3)	N4—C8—C9	109.5 (2)
N1—C1—N4	108.8 (3)	N5—C8—C10	112.2 (2)
N1—C1—C2	131.4 (3)	N4—C8—C10	108.1 (2)
N4—C1—C2	119.8 (2)	C9—C8—C10	112.4 (3)
C3—C2—C7	120.2 (3)	C8—C9—H9A	109.5
C3—C2—C1	124.0 (3)	C8—C9—H9B	109.5
C7—C2—C1	115.7 (3)	H9A—C9—H9B	109.5
C4—C3—C2	120.6 (3)	C8—C9—H9C	109.5
C4—C3—H3A	119.7	H9A—C9—H9C	109.5
C2—C3—H3A	119.7	H9B—C9—H9C	109.5
C3—C4—C5	118.3 (3)	C8—C10—H10A	109.5
C3—C4—H4A	120.9	C8—C10—H10B	109.5
C5—C4—H4A	120.9	H10A—C10—H10B	109.5
C6—C5—C4	122.7 (3)	C8—C10—H10C	109.5
C6—C5—Cl1	118.8 (2)	H10A—C10—H10C	109.5
C4—C5—Cl1	118.5 (2)	H10B—C10—H10C	109.5
C1—N1—N2—N3	−0.1 (3)	C4—C5—C6—C7	−0.8 (4)
N1—N2—N3—N4	0.4 (3)	Cl1—C5—C6—C7	179.5 (2)
N2—N3—N4—C1	−0.7 (3)	C8—N5—C7—C6	−153.7 (3)
N2—N3—N4—C8	−175.8 (2)	C8—N5—C7—C2	31.3 (4)
N2—N1—C1—N4	−0.3 (3)	C5—C6—C7—N5	−174.1 (3)
N2—N1—C1—C2	179.9 (3)	C5—C6—C7—C2	1.0 (4)
N3—N4—C1—N1	0.6 (3)	C3—C2—C7—N5	174.4 (3)
C8—N4—C1—N1	175.6 (2)	C1—C2—C7—N5	−4.6 (4)
N3—N4—C1—C2	−179.6 (2)	C3—C2—C7—C6	−0.7 (4)
C8—N4—C1—C2	−4.6 (4)	C1—C2—C7—C6	−179.7 (2)
N1—C1—C2—C3	−7.2 (5)	C7—N5—C8—N4	−38.5 (3)
N4—C1—C2—C3	173.0 (3)	C7—N5—C8—C9	−155.9 (3)
N1—C1—C2—C7	171.7 (3)	C7—N5—C8—C10	78.4 (3)
N4—C1—C2—C7	−8.0 (4)	C1—N4—C8—N5	25.7 (4)
C7—C2—C3—C4	0.2 (4)	N3—N4—C8—N5	−159.9 (2)
C1—C2—C3—C4	179.2 (3)	C1—N4—C8—C9	143.2 (3)
C2—C3—C4—C5	−0.1 (4)	N3—N4—C8—C9	−42.5 (4)
C3—C4—C5—C6	0.4 (4)	C1—N4—C8—C10	−94.0 (3)
C3—C4—C5—Cl1	−179.9 (2)	N3—N4—C8—C10	80.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H1N5···N1i	0.85 (4)	2.35 (4)	3.190 (3)	173 (6)
N5—H1N5···N2i	0.85 (4)	2.57 (4)	3.326 (3)	150 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H1N5⋯N1i	0.85 (4)	2.35 (4)	3.190 (3)	173 (6)
N5—H1N5⋯N2i	0.85 (4)	2.57 (4)	3.326 (3)	150 (4)

Symmetry code: (i) .