12-(4-Chloro-phen-yl)-7-methyl-10-phenyl-3,4,5,6,8,10-hexa-aza-tricyclo-[7.3.0.0]dodeca-1(9),2,4,7,11-penta-ene.

The 12 non-H atoms defining the triple-fused-ring system in the title compound, C(19)H(13)ClN(6), are almost coplanar (r.m.s. deviation = 0.023 Å). The chloro-substituted ring is almost effectively coplanar with the central atoms [dihedral angle = 6.74 (13)°], but the N-bound benzene ring is not [dihedral angle = 54.38 (13)°]. In the crystal, supra-molecular chains along the a axis sustained by C-H⋯π and π-π [centroid-centroid distance between N(4)C and C(4)N five-membered rings = 3.484 (2) Å] stacking occur. A very long C-Cl⋯π contact is also seen.

Related literature

For biological activity of imidazoles, see: Yohjiro et al. (1990 ▶). For related structures, see: Jotani et al. (2010a ▶,b ▶). Semi-empirical quantum chemical calculations were performed using MOPAC2009, see: Stewart (2009 ▶).

Experimental

Crystal data

C19H13ClN6

M = 360.80

Orthorhombic,

a = 6.9459 (5) Å

b = 9.7010 (8) Å

c = 24.0382 (16) Å

V = 1619.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.40 × 0.22 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.928, T max = 0.975

8751 measured reflections

1677 independent reflections

1405 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 0.98

1677 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048373/hb5751sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048373/hb5751Isup2.hkl

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

C19H13ClN6	F(000) = 744
Mr = 360.80	Dx = 1.480 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3699 reflections
a = 6.9459 (5) Å	θ = 2.3–29.6°
b = 9.7010 (8) Å	µ = 0.25 mm−1
c = 24.0382 (16) Å	T = 293 K
V = 1619.7 (2) Å3	Block, colourless
Z = 4	0.40 × 0.22 × 0.15 mm

Bruker SMART APEX CCD diffractometer	1677 independent reflections
Radiation source: fine-focus sealed tube	1405 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω and φ scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→4
Tmin = 0.928, Tmax = 0.975	k = −11→11
8751 measured reflections	l = −27→28

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.066P)2] where P = (Fo2 + 2Fc2)/3
1677 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.39113 (13)	0.63434 (9)	0.75124 (3)	0.0425 (3)
N1	0.4515 (4)	0.4484 (3)	0.42147 (10)	0.0298 (6)
N2	0.4434 (4)	0.2102 (3)	0.39545 (10)	0.0298 (6)
N3	0.4374 (4)	0.0610 (3)	0.47095 (10)	0.0283 (6)
N4	0.4365 (5)	−0.0648 (3)	0.49607 (11)	0.0376 (7)
N5	0.4374 (5)	−0.0389 (3)	0.54866 (12)	0.0425 (8)
N6	0.4393 (5)	0.0980 (3)	0.56050 (11)	0.0361 (7)
C1	0.4475 (5)	0.3117 (3)	0.43459 (12)	0.0278 (7)
C2	0.4411 (5)	0.2987 (3)	0.49267 (11)	0.0245 (7)
C3	0.4383 (5)	0.4353 (3)	0.51533 (12)	0.0273 (7)
C4	0.4465 (5)	0.5218 (3)	0.47005 (13)	0.0301 (7)
H4	0.4484	0.6175	0.4722	0.036*
C5	0.4366 (5)	0.0842 (3)	0.41388 (13)	0.0300 (7)
C6	0.4393 (5)	0.1602 (3)	0.51112 (12)	0.0281 (7)
C7	0.4230 (6)	−0.0361 (4)	0.37716 (14)	0.0405 (9)
H7A	0.2920	−0.0674	0.3758	0.061*
H7B	0.5037	−0.1085	0.3912	0.061*
H7C	0.4645	−0.0111	0.3404	0.061*
C8	0.4640 (5)	0.5089 (3)	0.36712 (12)	0.0289 (8)
C9	0.6114 (5)	0.4716 (4)	0.33131 (13)	0.0349 (8)
H9	0.7011	0.4051	0.3416	0.042*
C10	0.6221 (6)	0.5346 (4)	0.28045 (13)	0.0408 (9)
H10	0.7186	0.5087	0.2557	0.049*
C11	0.4940 (5)	0.6351 (4)	0.26511 (13)	0.0394 (9)
H11	0.5054	0.6785	0.2308	0.047*
C12	0.3477 (5)	0.6713 (4)	0.30125 (13)	0.0396 (9)
H12	0.2596	0.7390	0.2912	0.048*
C13	0.3322 (5)	0.6070 (4)	0.35236 (13)	0.0358 (8)
H13	0.2329	0.6304	0.3765	0.043*
C14	0.4292 (5)	0.4834 (3)	0.57356 (12)	0.0276 (7)
C15	0.4074 (5)	0.6233 (3)	0.58553 (13)	0.0315 (7)
H15	0.3997	0.6860	0.5564	0.038*
C16	0.3968 (5)	0.6708 (3)	0.63951 (13)	0.0336 (8)
H16	0.3824	0.7644	0.6467	0.040*
C17	0.4079 (5)	0.5776 (3)	0.68284 (12)	0.0300 (7)
C18	0.4282 (5)	0.4389 (3)	0.67246 (13)	0.0340 (8)
H18	0.4342	0.3768	0.7019	0.041*
C19	0.4397 (5)	0.3921 (3)	0.61828 (12)	0.0319 (7)
H19	0.4548	0.2983	0.6115	0.038*

	U11	U22	U33	U12	U13	U23
Cl1	0.0529 (6)	0.0401 (5)	0.0344 (4)	−0.0031 (4)	0.0028 (4)	−0.0066 (4)
N1	0.0367 (16)	0.0210 (15)	0.0317 (14)	−0.0009 (13)	0.0002 (12)	0.0045 (12)
N2	0.0289 (15)	0.0257 (16)	0.0348 (14)	−0.0007 (14)	−0.0003 (12)	−0.0003 (12)
N3	0.0281 (15)	0.0209 (14)	0.0358 (14)	−0.0017 (12)	0.0016 (12)	−0.0010 (12)
N4	0.0465 (19)	0.0210 (15)	0.0453 (18)	−0.0009 (15)	0.0005 (14)	0.0049 (13)
N5	0.061 (2)	0.0213 (17)	0.0457 (18)	−0.0007 (16)	0.0016 (16)	0.0061 (14)
N6	0.0501 (18)	0.0232 (16)	0.0349 (16)	−0.0033 (14)	0.0033 (13)	0.0065 (12)
C1	0.0252 (17)	0.0243 (18)	0.0339 (17)	0.0003 (15)	0.0006 (14)	0.0015 (14)
C2	0.0231 (17)	0.0235 (17)	0.0269 (15)	0.0006 (15)	0.0011 (13)	0.0036 (13)
C3	0.0260 (17)	0.0229 (17)	0.0329 (17)	0.0016 (15)	−0.0016 (14)	0.0033 (14)
C4	0.0365 (19)	0.0214 (18)	0.0323 (17)	−0.0015 (15)	0.0007 (15)	−0.0013 (14)
C5	0.0238 (18)	0.0308 (19)	0.0355 (18)	0.0000 (15)	0.0017 (14)	−0.0022 (15)
C6	0.0233 (17)	0.0260 (18)	0.0350 (17)	0.0001 (15)	0.0020 (13)	0.0004 (14)
C7	0.043 (2)	0.030 (2)	0.048 (2)	0.0006 (18)	0.0033 (18)	−0.0072 (16)
C8	0.0356 (19)	0.0227 (18)	0.0286 (17)	−0.0026 (15)	−0.0030 (14)	0.0036 (14)
C9	0.035 (2)	0.031 (2)	0.0384 (18)	0.0043 (16)	0.0018 (15)	0.0023 (16)
C10	0.044 (2)	0.045 (2)	0.0336 (19)	−0.0009 (19)	0.0070 (15)	0.0038 (17)
C11	0.054 (2)	0.031 (2)	0.0338 (19)	−0.0061 (17)	−0.0049 (15)	0.0061 (17)
C12	0.053 (2)	0.032 (2)	0.0336 (18)	0.0090 (17)	−0.0063 (16)	0.0038 (16)
C13	0.043 (2)	0.031 (2)	0.0330 (18)	0.0033 (16)	0.0013 (14)	−0.0008 (16)
C14	0.0256 (18)	0.0259 (18)	0.0314 (16)	−0.0047 (15)	0.0011 (14)	−0.0022 (14)
C15	0.038 (2)	0.0224 (17)	0.0341 (17)	0.0005 (16)	−0.0012 (14)	0.0057 (15)
C16	0.035 (2)	0.0216 (18)	0.0443 (19)	−0.0005 (14)	0.0002 (15)	−0.0034 (16)
C17	0.0268 (18)	0.033 (2)	0.0304 (16)	−0.0015 (14)	−0.0010 (13)	−0.0010 (14)
C18	0.041 (2)	0.0290 (19)	0.0325 (17)	−0.0014 (17)	0.0019 (15)	0.0067 (15)
C19	0.0369 (18)	0.0220 (18)	0.0366 (18)	−0.0036 (16)	−0.0021 (15)	0.0037 (14)

Cl1—C17	1.738 (3)	C8—C13	1.368 (5)
N1—C1	1.364 (4)	C8—C9	1.386 (5)
N1—C4	1.368 (4)	C9—C10	1.369 (5)
N1—C8	1.435 (4)	C9—H9	0.9300
N2—C5	1.301 (4)	C10—C11	1.370 (5)
N2—C1	1.362 (4)	C10—H10	0.9300
N3—C6	1.364 (4)	C11—C12	1.382 (5)
N3—N4	1.361 (4)	C11—H11	0.9300
N3—C5	1.390 (4)	C12—C13	1.382 (5)
N4—N5	1.289 (4)	C12—H12	0.9300
N5—N6	1.359 (4)	C13—H13	0.9300
N6—C6	1.332 (4)	C14—C19	1.395 (4)
C1—C2	1.402 (4)	C14—C15	1.395 (4)
C2—C6	1.415 (4)	C15—C16	1.379 (4)
C2—C3	1.433 (4)	C15—H15	0.9300
C3—C4	1.376 (4)	C16—C17	1.382 (4)
C3—C14	1.477 (4)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.375 (5)
C5—C7	1.466 (4)	C18—C19	1.382 (4)
C7—H7A	0.9600	C18—H18	0.9300
C7—H7B	0.9600	C19—H19	0.9300
C7—H7C	0.9600
C1—N1—C4	108.0 (3)	C13—C8—N1	118.7 (3)
C1—N1—C8	127.6 (3)	C9—C8—N1	120.2 (3)
C4—N1—C8	124.5 (3)	C10—C9—C8	118.6 (3)
C5—N2—C1	116.4 (3)	C10—C9—H9	120.7
C6—N3—N4	108.6 (2)	C8—C9—H9	120.7
C6—N3—C5	125.8 (3)	C9—C10—C11	121.5 (3)
N4—N3—C5	125.7 (3)	C9—C10—H10	119.2
N5—N4—N3	105.1 (3)	C11—C10—H10	119.2
N4—N5—N6	113.3 (3)	C10—C11—C12	119.3 (3)
C6—N6—N5	104.9 (3)	C10—C11—H11	120.4
N2—C1—N1	122.9 (3)	C12—C11—H11	120.4
N2—C1—C2	128.5 (3)	C11—C12—C13	120.1 (3)
N1—C1—C2	108.5 (3)	C11—C12—H12	120.0
C1—C2—C6	113.4 (3)	C13—C12—H12	120.0
C1—C2—C3	107.2 (3)	C8—C13—C12	119.5 (3)
C6—C2—C3	139.4 (3)	C8—C13—H13	120.2
C4—C3—C2	105.2 (3)	C12—C13—H13	120.2
C4—C3—C14	124.0 (3)	C19—C14—C15	117.7 (3)
C2—C3—C14	130.8 (3)	C19—C14—C3	121.9 (3)
N1—C4—C3	111.0 (3)	C15—C14—C3	120.5 (3)
N1—C4—H4	124.5	C16—C15—C14	121.7 (3)
C3—C4—H4	124.5	C16—C15—H15	119.2
N2—C5—N3	119.2 (3)	C14—C15—H15	119.2
N2—C5—C7	123.0 (3)	C17—C16—C15	119.2 (3)
N3—C5—C7	117.7 (3)	C17—C16—H16	120.4
N6—C6—N3	108.1 (3)	C15—C16—H16	120.4
N6—C6—C2	135.2 (3)	C18—C17—C16	120.6 (3)
N3—C6—C2	116.7 (3)	C18—C17—Cl1	119.2 (2)
C5—C7—H7A	109.5	C16—C17—Cl1	120.1 (3)
C5—C7—H7B	109.5	C17—C18—C19	119.9 (3)
H7A—C7—H7B	109.5	C17—C18—H18	120.0
C5—C7—H7C	109.5	C19—C18—H18	120.0
H7A—C7—H7C	109.5	C18—C19—C14	121.0 (3)
H7B—C7—H7C	109.5	C18—C19—H19	119.5
C13—C8—C9	121.0 (3)	C14—C19—H19	119.5
C6—N3—N4—N5	0.2 (4)	N4—N3—C6—C2	179.8 (3)
C5—N3—N4—N5	−179.9 (3)	C5—N3—C6—C2	−0.1 (5)
N3—N4—N5—N6	−0.1 (4)	C1—C2—C6—N6	177.8 (4)
N4—N5—N6—C6	0.1 (4)	C3—C2—C6—N6	−2.2 (8)
C5—N2—C1—N1	−178.9 (3)	C1—C2—C6—N3	−2.2 (4)
C5—N2—C1—C2	−1.5 (5)	C3—C2—C6—N3	177.9 (4)
C4—N1—C1—N2	177.4 (3)	C1—N1—C8—C13	128.3 (4)
C8—N1—C1—N2	−4.1 (5)	C4—N1—C8—C13	−53.5 (5)
C4—N1—C1—C2	−0.4 (4)	C1—N1—C8—C9	−54.1 (5)
C8—N1—C1—C2	178.1 (3)	C4—N1—C8—C9	124.2 (4)
N2—C1—C2—C6	3.2 (5)	C13—C8—C9—C10	−0.4 (5)
N1—C1—C2—C6	−179.1 (3)	N1—C8—C9—C10	−178.0 (3)
N2—C1—C2—C3	−176.8 (3)	C8—C9—C10—C11	1.6 (5)
N1—C1—C2—C3	0.9 (4)	C9—C10—C11—C12	−1.6 (6)
C1—C2—C3—C4	−1.0 (4)	C10—C11—C12—C13	0.4 (5)
C6—C2—C3—C4	179.0 (4)	C9—C8—C13—C12	−0.8 (5)
C1—C2—C3—C14	179.1 (3)	N1—C8—C13—C12	176.8 (3)
C6—C2—C3—C14	−1.0 (7)	C11—C12—C13—C8	0.8 (5)
C1—N1—C4—C3	−0.3 (4)	C4—C3—C14—C19	−173.7 (3)
C8—N1—C4—C3	−178.8 (3)	C2—C3—C14—C19	6.2 (6)
C2—C3—C4—N1	0.8 (4)	C4—C3—C14—C15	7.0 (5)
C14—C3—C4—N1	−179.3 (3)	C2—C3—C14—C15	−173.1 (3)
C1—N2—C5—N3	−1.1 (5)	C19—C14—C15—C16	0.1 (5)
C1—N2—C5—C7	177.3 (3)	C3—C14—C15—C16	179.5 (3)
C6—N3—C5—N2	2.0 (5)	C14—C15—C16—C17	−0.1 (5)
N4—N3—C5—N2	−178.0 (3)	C15—C16—C17—C18	−0.3 (5)
C6—N3—C5—C7	−176.5 (3)	C15—C16—C17—Cl1	−179.0 (3)
N4—N3—C5—C7	3.5 (5)	C16—C17—C18—C19	0.7 (5)
N5—N6—C6—N3	0.0 (4)	Cl1—C17—C18—C19	179.3 (3)
N5—N6—C6—C2	−179.9 (4)	C17—C18—C19—C14	−0.6 (5)
N4—N3—C6—N6	−0.1 (4)	C15—C14—C19—C18	0.2 (5)
C5—N3—C6—N6	179.9 (3)	C3—C14—C19—C18	−179.1 (3)

Cg1 and Cg2 are the centroids of the C14–C19 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7a···Cg1i	0.96	2.62	3.509 (5)	154
C17—Cl1···Cg2ii	1.737 (4)	3.608 (2)	4.423 (4)	106.34 (13)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C14–C19 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7a⋯Cg1i	0.96	2.62	3.509 (5)	154
C17—Cl1⋯Cg2ii	1.74 (1)	3.61 (1)	4.423 (4)	106 (1)

Symmetry codes: (i) ; (ii) .