6-Phenyl-5,6-dihydro­benzoimidazo[1,2-c]quinazoline

Mahendra, M.; Gayathri, V.; Jayalakshmi, K.; Rangappa, K.S.; Sridhar, M.A.; Shashidhara Prasad, J.

doi:10.1107/S1600536805028655

6-Phenyl-5,6-dihydrobenzoimidazo[1,2-c]quinazoline

M. Mahendra, V. Gayathri, K. Jayalakshmi, K. S. Rangappa, M. A. Sridhar and J. Shashidhara Prasad

In the title compound, C₂₀H₁₅N₃, the molecules are linked by N—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028655/is6119sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028655/is6119Isup2.hkl Contains datablock I

CCDC reference: 287606

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R factor = 0.047
wR factor = 0.144
Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93

Author Response: ...We have collected data on kappa IP diffractometer and processed using Denzo; and as we know that the DENZO image processing package is known to have problems with certain strong reflections. They are often excluded from the data set leading to a lower value for the above parameter.


Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.03
           From the CIF: _diffrn_reflns_theta_full          25.03
           From the CIF: _reflns_number_total               2441
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2639
           Completeness (_total/calc)             92.50%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The quinazoline ring is widely found in alkaloids and many biologically active compounds. Substituted quinazoline have fungicidal, antimicrobial, anti-inflammatory, anticancer, antihypertensive and anti-HIV activities (Alexandre et al., 2003; De Clercq, 2001). Few X-ray crystal structure reports for benzimidazoquinazolines has been carried out (Elgemeie, et al., 1998; Low et al., 2003; Jayalakshmi, et al., 2004). In view of the above observations, the title compound, (I), was synthesized and its crystal structure is reported here (Fig. 1).

Most of the bond lengths and angles have normal values and are comparable to those reported in similar structures (Elgemeie et al., 1998; Low et al., 2002, 2003; Jayalakshmi et al., 2004). The phenyl and imidazole rings are planar, but the quinazoline ring sytem deviates from planarity, with atom C10 lying 0.4707 (16) Å from the N7/C8/C13/C12/N11 least-squares plane. The phenyl ring at C10 is nearly perpendicular to the quinazoline ring sytem, with a dihedral angle of 86.99 (9)°. The crystal packing is stabilized by an intermolecular N11—H11···N9ⁱ (symmetry code as in Table 2) hydrogen bond, which links the molecules into a zigzag chain along the b axis (Fig. 2).

Experimental top

A mixture of o-aminophenylbenzimidazole (o-APB, 0.05 mol, 10.45 g) and benzaldehyde (0.05 mol, 5.30 g)/p-chlorobenzaldehyde (0.05 mol: 7.30 g) was refluxed in ethanol (200 ml) for 5 h. The resulting solution was concentrated under reduced pressure to a small volume to obtain a cream compound. The solid was recrystallized from ethanol to give the white crystalline compound (I) (yield 70%; m.p. 472 K).

Computing details top

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. View of (I), with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing in (I), viewed down the b axis. Dashed lines indicate hydrogen bonds.

6-Phenyl-5,6-dihydrobenzoimidazo[1,2-c]quinazoline top

Crystal data top

C₂₀H₁₅N₃	F(000) = 624
M_r = 297.35	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4596 reflections
a = 11.5690 (8) Å	θ = 2.6–25.0°
b = 9.9150 (7) Å	µ = 0.08 mm⁻¹
c = 14.337 (1) Å	T = 295 K
β = 114.086 (4)°	Block, white
V = 1501.36 (19) Å³	0.25 × 0.2 × 0.2 mm
Z = 4

Data collection top

MacScience DIPLabo 32001 diffractometer	2133 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.0°, θ_min = 2.6°
Detector resolution: 10.0 pixels mm^-1	h = −13→13
ω scans	k = −11→11
4596 measured reflections	l = −16→16
2441 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0844P)² + 0.1702P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max < 0.001
2441 reflections	Δρ_max = 0.31 e Å⁻³
209 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.172 (16)

Crystal data top

C₂₀H₁₅N₃	V = 1501.36 (19) Å³
M_r = 297.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5690 (8) Å	µ = 0.08 mm⁻¹
b = 9.9150 (7) Å	T = 295 K
c = 14.337 (1) Å	0.25 × 0.2 × 0.2 mm
β = 114.086 (4)°

Data collection top

MacScience DIPLabo 32001 diffractometer	2133 reflections with I > 2σ(I)
4596 measured reflections	R_int = 0.025
2441 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.18	Δρ_max = 0.31 e Å⁻³
2441 reflections	Δρ_min = −0.39 e Å⁻³
209 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2, conventional R-factors R are based on F, with F set to zero for negative F^2. The observed criterion of F^2 > σ(F^2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2 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	U_iso*/U_eq
N7	0.30479 (13)	0.60613 (13)	0.22364 (10)	0.0411 (4)
N9	0.26562 (14)	0.82728 (14)	0.19323 (11)	0.0467 (5)
N11	0.47306 (13)	0.49796 (15)	0.20486 (11)	0.0509 (5)
C1	0.17219 (17)	0.56599 (19)	0.32454 (13)	0.0508 (6)
C2	0.22511 (15)	0.64081 (16)	0.27005 (11)	0.0410 (5)
C3	0.20311 (15)	0.77899 (16)	0.25140 (13)	0.0430 (5)
C4	0.12682 (17)	0.8466 (2)	0.28995 (14)	0.0531 (6)
C5	0.07332 (18)	0.7730 (2)	0.34358 (15)	0.0569 (7)
C6	0.09557 (18)	0.6355 (2)	0.36069 (15)	0.0573 (7)
C8	0.32275 (15)	0.72036 (15)	0.17741 (12)	0.0398 (5)
C10	0.35563 (15)	0.47405 (16)	0.21616 (12)	0.0410 (5)
C12	0.48247 (15)	0.59772 (17)	0.14146 (12)	0.0442 (5)
C13	0.40490 (15)	0.71253 (16)	0.12324 (12)	0.0424 (5)
C14	0.57280 (17)	0.5933 (2)	0.10027 (14)	0.0535 (6)
C15	0.58109 (19)	0.6972 (2)	0.04000 (15)	0.0605 (7)
C16	0.5008 (2)	0.8068 (2)	0.01755 (15)	0.0593 (7)
C17	0.41320 (17)	0.81513 (18)	0.06004 (13)	0.0501 (6)
C18	0.26056 (14)	0.38823 (15)	0.13165 (11)	0.0372 (5)
C19	0.17476 (15)	0.44245 (17)	0.04049 (12)	0.0447 (5)
C20	0.09414 (17)	0.35867 (19)	−0.03549 (13)	0.0518 (6)
C21	0.09769 (18)	0.22142 (18)	−0.02126 (14)	0.0529 (6)
C22	0.18212 (18)	0.16652 (18)	0.06878 (15)	0.0546 (6)
C23	0.26249 (17)	0.24989 (17)	0.14473 (13)	0.0482 (6)
H1	0.18750	0.47410	0.33600	0.0610*
H4	0.11240	0.93880	0.27980	0.0640*
H5	0.02100	0.81640	0.36900	0.0680*
H6	0.05790	0.58920	0.39740	0.0690*
H10	0.37630	0.42700	0.28110	0.0490*
H11	0.53810	0.44880	0.23850	0.0610*
H14	0.62740	0.52000	0.11370	0.0640*
H15	0.64230	0.69350	0.01360	0.0730*
H16	0.50560	0.87440	−0.02570	0.0710*
H17	0.35970	0.88940	0.04640	0.0600*
H19	0.17140	0.53530	0.03040	0.0540*
H20	0.03720	0.39560	−0.09660	0.0620*
H21	0.04300	0.16580	−0.07250	0.0640*
H22	0.18510	0.07360	0.07850	0.0660*
H23	0.31900	0.21230	0.20580	0.0580*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N7	0.0432 (8)	0.0391 (8)	0.0425 (7)	0.0004 (5)	0.0190 (6)	−0.0027 (5)
N9	0.0491 (9)	0.0406 (8)	0.0550 (8)	−0.0006 (6)	0.0258 (7)	−0.0039 (6)
N11	0.0364 (8)	0.0525 (9)	0.0599 (9)	0.0075 (6)	0.0156 (7)	0.0055 (7)
C1	0.0561 (12)	0.0488 (10)	0.0515 (9)	−0.0039 (8)	0.0261 (9)	−0.0017 (8)
C2	0.0398 (9)	0.0452 (9)	0.0385 (8)	−0.0034 (6)	0.0166 (7)	−0.0072 (7)
C3	0.0420 (10)	0.0437 (9)	0.0441 (9)	−0.0024 (6)	0.0183 (8)	−0.0062 (7)
C4	0.0544 (11)	0.0487 (10)	0.0607 (11)	0.0017 (8)	0.0281 (9)	−0.0087 (8)
C5	0.0553 (12)	0.0645 (12)	0.0612 (11)	−0.0022 (9)	0.0343 (10)	−0.0141 (9)
C6	0.0607 (12)	0.0647 (12)	0.0584 (11)	−0.0070 (9)	0.0366 (10)	−0.0046 (9)
C8	0.0387 (9)	0.0388 (9)	0.0404 (8)	−0.0020 (6)	0.0145 (7)	−0.0026 (6)
C10	0.0432 (10)	0.0393 (9)	0.0397 (8)	0.0064 (6)	0.0162 (7)	0.0037 (6)
C12	0.0379 (9)	0.0481 (10)	0.0436 (8)	−0.0036 (6)	0.0137 (7)	−0.0097 (7)
C13	0.0394 (10)	0.0467 (10)	0.0413 (8)	−0.0048 (6)	0.0168 (8)	−0.0068 (7)
C14	0.0447 (11)	0.0617 (11)	0.0560 (10)	−0.0018 (8)	0.0226 (9)	−0.0163 (9)
C15	0.0588 (12)	0.0753 (14)	0.0597 (11)	−0.0125 (9)	0.0367 (10)	−0.0189 (10)
C16	0.0683 (13)	0.0647 (12)	0.0551 (11)	−0.0117 (9)	0.0357 (10)	−0.0045 (9)
C17	0.0528 (11)	0.0509 (10)	0.0490 (10)	−0.0034 (7)	0.0231 (9)	−0.0031 (7)
C18	0.0384 (9)	0.0375 (8)	0.0401 (8)	0.0049 (6)	0.0205 (7)	0.0021 (6)
C19	0.0484 (10)	0.0367 (9)	0.0456 (9)	0.0052 (6)	0.0158 (8)	0.0041 (6)
C20	0.0483 (11)	0.0562 (10)	0.0437 (9)	0.0020 (8)	0.0113 (8)	0.0014 (8)
C21	0.0539 (12)	0.0506 (11)	0.0543 (10)	−0.0067 (8)	0.0221 (9)	−0.0125 (8)
C22	0.0615 (12)	0.0366 (9)	0.0674 (11)	−0.0002 (7)	0.0279 (10)	−0.0018 (8)
C23	0.0529 (11)	0.0418 (9)	0.0480 (9)	0.0065 (7)	0.0188 (8)	0.0070 (7)

Geometric parameters (Å, º) top

N7—C2	1.383 (2)	C16—C17	1.382 (3)
N7—C8	1.370 (2)	C18—C23	1.383 (2)
N7—C10	1.457 (2)	C18—C19	1.387 (2)
N9—C3	1.393 (2)	C19—C20	1.385 (2)
N9—C8	1.317 (2)	C20—C21	1.374 (3)
N11—C10	1.452 (2)	C21—C22	1.374 (3)
N11—C12	1.377 (2)	C22—C23	1.381 (3)
N11—H11	0.8603	C1—H1	0.9299
C1—C2	1.388 (3)	C4—H4	0.9300
C1—C6	1.380 (3)	C5—H5	0.9297
C2—C3	1.399 (2)	C6—H6	0.9300
C3—C4	1.390 (3)	C10—H10	0.9798
C4—C5	1.377 (3)	C14—H14	0.9301
C5—C6	1.391 (3)	C15—H15	0.9300
C8—C13	1.454 (3)	C16—H16	0.9300
C10—C18	1.521 (2)	C17—H17	0.9299
C12—C13	1.406 (2)	C19—H19	0.9303
C12—C14	1.395 (3)	C20—H20	0.9298
C13—C17	1.391 (2)	C21—H21	0.9299
C14—C15	1.373 (3)	C22—H22	0.9303
C15—C16	1.380 (3)	C23—H23	0.9304

N7···N9	2.2455 (19)	C20···H15^v	2.9803
N9···N7	2.2455 (19)	C21···H15^v	3.0826
N9···N11ⁱ	3.245 (2)	C22···H15^v	3.0668
N11···N9ⁱⁱ	3.245 (2)	C23···H15^v	2.9533
N7···H19	2.6572	H1···C10	3.0762
N9···H17	2.8046	H6···H21^viii	2.5825
N9···H11ⁱ	2.3983	H10···C1	3.0105
N9···H22ⁱⁱⁱ	2.8788	H10···H23	2.3563
C1···C17^iv	3.589 (3)	H10···C16ⁱⁱ	2.9026
C8···C19	3.411 (2)	H10···C17ⁱⁱ	2.7966
C10···C17ⁱⁱ	3.595 (2)	H11···H14	2.5052
C12···C19	3.596 (3)	H11···N9ⁱⁱ	2.3983
C14···C15^v	3.548 (3)	H11···C8ⁱⁱ	2.7552
C14···C14^v	3.252 (3)	H11···C13ⁱⁱ	2.9640
C15···C14^v	3.548 (3)	H11···C17ⁱⁱ	3.0147
C17···C10ⁱ	3.595 (2)	H14···H11	2.5052
C17···C1^vi	3.589 (3)	H15···C18^v	2.8577
C19···C12	3.596 (3)	H15···C19^v	2.8701
C19···C8	3.411 (2)	H15···C20^v	2.9803
C1···H10	3.0105	H15···C21^v	3.0826
C1···H17^iv	3.0638	H15···C22^v	3.0668
C2···H20^vii	3.0601	H15···C23^v	2.9533
C3···H21^vii	3.0041	H17···N9	2.8046
C4···H21^vii	2.9317	H17···C1^vi	3.0638
C5···H19^iv	3.0974	H19···N7	2.6572
C8···H19	2.8041	H19···C8	2.8041
C8···H11ⁱ	2.7552	H19···C13	3.0368
C10···H1	3.0762	H19···C5^vi	3.0974
C12···H23ⁱ	2.6937	H20···C2^vii	3.0601
C13···H11ⁱ	2.9640	H21···C3^vii	3.0041
C13···H19	3.0368	H21···C4^vii	2.9317
C14···H23ⁱ	2.8016	H21···H6^ix	2.5825
C16···H10ⁱ	2.9026	H22···N9^x	2.8788
C17···H10ⁱ	2.7966	H23···H10	2.3563
C17···H11ⁱ	3.0147	H23···C12ⁱⁱ	2.6937
C18···H15^v	2.8577	H23···C14ⁱⁱ	2.8016
C19···H15^v	2.8701

C2—N7—C8	106.84 (13)	C10—C18—C23	118.70 (14)
C2—N7—C10	128.85 (14)	C18—C19—C20	120.14 (16)
C8—N7—C10	124.17 (15)	C19—C20—C21	120.50 (17)
C3—N9—C8	104.25 (14)	C20—C21—C22	119.90 (17)
C10—N11—C12	121.36 (15)	C21—C22—C23	119.70 (17)
C10—N11—H11	119.28	C18—C23—C22	121.21 (16)
C12—N11—H11	119.35	C2—C1—H1	121.82
C2—C1—C6	116.30 (17)	C6—C1—H1	121.88
N7—C2—C3	104.87 (14)	C3—C4—H4	120.95
N7—C2—C1	132.22 (16)	C5—C4—H4	121.04
C1—C2—C3	122.91 (17)	C4—C5—H5	119.12
C2—C3—C4	119.46 (17)	C6—C5—H5	119.20
N9—C3—C2	110.65 (15)	C1—C6—H6	119.16
N9—C3—C4	129.90 (16)	C5—C6—H6	119.21
C3—C4—C5	118.01 (18)	N7—C10—H10	107.89
C4—C5—C6	121.7 (2)	N11—C10—H10	107.89
C1—C6—C5	121.63 (19)	C18—C10—H10	107.90
N7—C8—C13	118.38 (14)	C12—C14—H14	119.98
N7—C8—N9	113.34 (16)	C15—C14—H14	120.04
N9—C8—C13	128.19 (15)	C14—C15—H15	119.14
N7—C10—C18	112.27 (14)	C16—C15—H15	119.22
N11—C10—C18	114.07 (14)	C15—C16—H16	120.37
N7—C10—N11	106.60 (13)	C17—C16—H16	120.33
C13—C12—C14	118.57 (16)	C13—C17—H17	119.93
N11—C12—C13	119.18 (16)	C16—C17—H17	119.98
N11—C12—C14	122.10 (16)	C18—C19—H19	119.90
C12—C13—C17	120.29 (17)	C20—C19—H19	119.96
C8—C13—C17	122.86 (16)	C19—C20—H20	119.72
C8—C13—C12	116.78 (14)	C21—C20—H20	119.78
C12—C14—C15	119.98 (19)	C20—C21—H21	120.03
C14—C15—C16	121.6 (2)	C22—C21—H21	120.06
C15—C16—C17	119.30 (19)	C21—C22—H22	120.12
C13—C17—C16	120.09 (18)	C23—C22—H22	120.18
C10—C18—C19	122.72 (14)	C18—C23—H23	119.41
C19—C18—C23	118.54 (15)	C22—C23—H23	119.38

C8—N7—C2—C1	177.75 (18)	C3—C4—C5—C6	1.0 (3)
C8—N7—C2—C3	−2.12 (17)	C4—C5—C6—C1	−0.1 (3)
C10—N7—C2—C1	1.9 (3)	N9—C8—C13—C17	−14.6 (3)
C10—N7—C2—C3	−178.02 (15)	N7—C8—C13—C12	−14.1 (2)
C2—N7—C8—N9	2.52 (19)	N7—C8—C13—C17	169.11 (16)
C2—N7—C8—C13	179.33 (14)	N9—C8—C13—C12	162.17 (17)
C10—N7—C8—N9	178.65 (15)	N7—C10—C18—C23	−147.38 (16)
C10—N7—C8—C13	−4.5 (2)	N11—C10—C18—C19	−86.5 (2)
C2—N7—C10—N11	−154.21 (15)	N11—C10—C18—C23	91.23 (19)
C2—N7—C10—C18	80.21 (19)	N7—C10—C18—C19	34.9 (2)
C8—N7—C10—N11	30.5 (2)	N11—C12—C13—C8	2.7 (2)
C8—N7—C10—C18	−95.04 (19)	C14—C12—C13—C8	−172.83 (16)
C8—N9—C3—C2	0.27 (19)	C14—C12—C13—C17	4.0 (2)
C8—N9—C3—C4	−179.50 (19)	N11—C12—C13—C17	179.57 (16)
C3—N9—C8—N7	−1.71 (19)	N11—C12—C14—C15	−177.98 (17)
C3—N9—C8—C13	−178.14 (17)	C13—C12—C14—C15	−2.6 (3)
C12—N11—C10—N7	−42.59 (19)	C8—C13—C17—C16	174.50 (17)
C12—N11—C10—C18	81.89 (19)	C12—C13—C17—C16	−2.2 (3)
C10—N11—C12—C13	28.4 (2)	C12—C14—C15—C16	−0.8 (3)
C10—N11—C12—C14	−156.28 (16)	C14—C15—C16—C17	2.7 (3)
C6—C1—C2—C3	−0.2 (3)	C15—C16—C17—C13	−1.2 (3)
C2—C1—C6—C5	−0.2 (3)	C23—C18—C19—C20	−0.6 (3)
C6—C1—C2—N7	179.90 (18)	C10—C18—C23—C22	−177.17 (18)
N7—C2—C3—N9	1.19 (19)	C19—C18—C23—C22	0.7 (3)
C1—C2—C3—N9	−178.70 (16)	C10—C18—C19—C20	177.18 (17)
C1—C2—C3—C4	1.1 (3)	C18—C19—C20—C21	0.4 (3)
N7—C2—C3—C4	−179.01 (16)	C19—C20—C21—C22	−0.3 (3)
N9—C3—C4—C5	178.33 (18)	C20—C21—C22—C23	0.4 (3)
C2—C3—C4—C5	−1.4 (3)	C21—C22—C23—C18	−0.6 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, y+1, z; (iv) x, −y+3/2, z+1/2; (v) −x+1, −y+1, −z; (vi) x, −y+3/2, z−1/2; (vii) −x, −y+1, −z; (viii) x, −y+1/2, z+1/2; (ix) x, −y+1/2, z−1/2; (x) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···N9ⁱⁱ	0.86	2.40	3.245 (2)	168

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅N₃
M_r	297.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.5690 (8), 9.9150 (7), 14.337 (1)
β (°)	114.086 (4)
V (Å³)	1501.36 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.2 × 0.2

Data collection
Diffractometer	MacScience DIPLabo 32001 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4596, 2441, 2133
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.144, 1.18
No. of reflections	2441
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.39

Computer programs: XPRESS (MacScience, 2002), SCALEPACK (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) top

N7—C2	1.383 (2)	N9—C8	1.317 (2)
N7—C8	1.370 (2)	N11—C10	1.452 (2)
N7—C10	1.457 (2)	N11—C12	1.377 (2)
N9—C3	1.393 (2)

C2—N7—C8	106.84 (13)	N7—C8—C13	118.38 (14)
C2—N7—C10	128.85 (14)	N7—C8—N9	113.34 (16)
C8—N7—C10	124.17 (15)	N9—C8—C13	128.19 (15)
C3—N9—C8	104.25 (14)	N7—C10—C18	112.27 (14)
C10—N11—C12	121.36 (15)	N11—C10—C18	114.07 (14)
N7—C2—C3	104.87 (14)	N7—C10—N11	106.60 (13)
N7—C2—C1	132.22 (16)	N11—C12—C13	119.18 (16)
N9—C3—C2	110.65 (15)	N11—C12—C14	122.10 (16)
N9—C3—C4	129.90 (16)