2-[(2-Phenyl-1,3-oxazol-4-yl)­methyl]-2H-1,2,3-benzotriazole

Swaleh, S.; Ziemer, B.

doi:10.1107/S1600536800018808

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2-[(2-Phenyl-1,3-oxazol-4-yl)methyl]-2H-1,2,3-benzotriazole

S. Swaleh and B. Ziemer

The title compound, C₁₆H₁₂N₄O, was obtained through a two-step process. There are two molecules in the asymmetric unit with essentially equal bond lengths. The phenyl and oxazole rings are essentially coplanar. Steric interactions between the two halves of the molecule produce a wide angle at the central C atom.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800018808/cf6013sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536800018808/cf6013Isup2.hkl Contains datablock I

CCDC reference: 155878

checkCIF report

Key indicators

Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.003 Å
R factor = 0.040
wR factor = 0.082
Data-to-parameter ratio = 8.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_741  Alert C Bond    Calc    1.390(2), Rep     1.39000 ....    Missing s.u.
                     C3   -C4      1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(2), Rep     1.39000 ....    Missing s.u.
                     C3   -C8      1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(3), Rep     1.39000 ....    Missing s.u.
                     C4   -C5      1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(3), Rep     1.39000 ....    Missing s.u.
                     C5   -C6      1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(3), Rep     1.39000 ....    Missing s.u.
                     C6   -C7      1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(3), Rep     1.39000 ....    Missing s.u.
                     C7   -C8      1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(2), Rep     1.39000 ....    Missing s.u.
                     C33  -C34     1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(3), Rep     1.39000 ....    Missing s.u.
                     C33  -C38     1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(3), Rep     1.39000 ....    Missing s.u.
                     C34  -C35     1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(3), Rep     1.39000 ....    Missing s.u.
                     C35  -C36     1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(3), Rep     1.39000 ....    Missing s.u.
                     C36  -C37     1.555   1.555

PLAT_741  Alert C Bond    Calc    1.390(3), Rep     1.39000 ....    Missing s.u.
                     C37  -C38     1.555   1.555

PLAT_742  Alert C Angle   Calc  119.99(16), Rep      120.00 ....    Missing s.u.
                     C4   -C3   -C8      1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  120.00(16), Rep      120.00 ....    Missing s.u.
                     C5   -C4   -C3      1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  120.00(15), Rep      120.00 ....    Missing s.u.
                     C4   -C5   -C6      1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  120.00(18), Rep      120.00 ....    Missing s.u.
                     C7   -C6   -C5      1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  120.01(17), Rep      120.00 ....    Missing s.u.
                     C8   -C7   -C6      1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  120.01(14), Rep      120.00 ....    Missing s.u.
                     C7   -C8   -C3      1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  120.00(17), Rep      120.00 ....    Missing s.u.
                     C34  -C33  -C38     1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  119.99(17), Rep      120.00 ....    Missing s.u.
                     C35  -C34  -C33     1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  120.00(15), Rep      120.00 ....    Missing s.u.
                     C36  -C35  -C34     1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  120.00(19), Rep      120.00 ....    Missing s.u.
                     C35  -C36  -C37     1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  120.00(17), Rep      120.00 ....    Missing s.u.
                     C38  -C37  -C36     1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc  120.00(15), Rep      120.00 ....    Missing s.u.
                     C37  -C38  -C33     1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C8  -C3  -C4  -C5     1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C3  -C4  -C5  -C6     1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C4  -C5  -C6  -C7     1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C5  -C6  -C7  -C8     1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C6  -C7  -C8  -C3     1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C4  -C3  -C8  -C7     1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C38 -C33 -C34 -C35    1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C33 -C34 -C35 -C36    1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C34 -C35 -C36 -C37    1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C35 -C36 -C37 -C38    1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C36 -C37 -C38 -C33    1.555   1.555   1.555   1.555

PLAT_743  Alert C Torsion Calc      0.0(3), Rep        0.00 ....    Missing s.u.
                     C34 -C33 -C38 -C37    1.555   1.555   1.555   1.555

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.90
         From the CIF: _reflns_number_total               2943
         Count of symmetry unique reflns         2982
         Completeness (_total/calc)             98.69%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 36 Alert Level C = Please check

Comment top

The title compound, (I), was obtained through a two-step process. By reaction of 5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole and a mixture of N-(1-cyanoethyl)benzenesulfonamide and benzotriazole in the presence of a base and small traces of DMSO, the N-alkylation took place with the more reactive benzotriazole. A halogen–lithium exchange reaction was conducted on the obtained product resulting in the formation of (I).

There are two molecules in the asymmetric unit. All corresponding bond lengths are equal within 2σ and in accordance with the chemical diagram. In both molecules, the dihedral angle between the phenyl and oxazole rings (less than 5°) indicates communicating π systems. The steric demand of the ring systems on the two sides of the molecule seems to have the effects (i) that the tetrahedral angle at the centre of the molecule formed by the non-H atoms is significantly enlarged to 112.0 (3) and 111.0 (3)° in the two molecules, respectively, and (ii) that the halves of the molecule are inclined to each other by about 43 and 33° in the two molecules.

Experimental top

Following the method of Lesbosquain & Decruix (1993), 5-bromo-4(bromomethyl)-2-phenyl-1,3-oxazole, K₂CO₃ and a mixture of N-(1-cyanoethyl)benzenesulfonamide and benzotriazole in the presence of traces of DMSO were refluxed in acetonitrile for 1 h. The resulting suspension was cooled, filtered and concentrated under reduced pressure, and the obtained compound was purified by column chromatography. Br–Li exchange reaction was further carried out on the purified compound at 173 K for 2 h, as already described by Swaleh & Liebscher (1999). The compound isolated by subsequent column chromatography was recrystallized from absolute ethanol, affording (I).

Computing details top

Data collection: IPDS2.87 (Stoe & Cie, 1997); cell refinement: IPDS2.87; data reduction: IPDS2.87; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: OPTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The structure of one molecule OF (I) showing 50% probability ellipsoids.

1-[(2-phenyl-1,3-oxazol-4-yl)methyl]-1H-1,2,3-benzotriazole top

Crystal data top

C₁₆H₁₂N₄O	D_x = 1.355 Mg m⁻³
M_r = 276.30	Melting point: 376(1) K
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 14.880 (2) Å	Cell parameters from 4003 reflections
b = 4.6251 (5) Å	θ = 3.1–24.3°
c = 20.043 (3) Å	µ = 0.09 mm⁻¹
β = 100.963 (19)°	T = 180 K
V = 1354.2 (3) Å³	Prism, colorless
Z = 4	0.52 × 0.24 × 0.12 mm
F(000) = 576

Data collection top

Stoe IPDS diffractometer	2202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	R_int = 0.068
Planar graphite monochromator	θ_max = 25.9°, θ_min = 2.3°
Detector resolution: 6.667 pixels mm^-1	h = −18→18
ϕ–rotation, ϕ–incr. = 1.2°, 183 exposures scans	k = −5→5
9269 measured reflections	l = −24→24
2943 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)] = 0.040	H-atom parameters not refined
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0401P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max = 0.001
2943 reflections	Δρ_max = 0.17 e Å⁻³
356 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (2)

Crystal data top

C₁₆H₁₂N₄O	V = 1354.2 (3) Å³
M_r = 276.30	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 14.880 (2) Å	µ = 0.09 mm⁻¹
b = 4.6251 (5) Å	T = 180 K
c = 20.043 (3) Å	0.52 × 0.24 × 0.12 mm
β = 100.963 (19)°

Data collection top

Stoe IPDS diffractometer	2202 reflections with I > 2σ(I)
9269 measured reflections	R_int = 0.068
2943 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.082	H-atom parameters not refined
S = 0.95	Δρ_max = 0.17 e Å⁻³
2943 reflections	Δρ_min = −0.16 e Å⁻³
356 parameters

Special details top

Experimental. Recrystallized from ethanol. During data collection the crystal was in cold N₂ gas of the Cryostream Cooler (Oxford Cryosystems, 1992) mounted on a ϕ-axis diffractometer supplied with an area detector.

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	U_iso*/U_eq
C2	0.06870 (17)	0.0245 (7)	0.15417 (12)	0.0290 (7)
C3	0.05480 (11)	−0.1832 (4)	0.20681 (8)	0.0299 (7)
C4	−0.03202 (10)	−0.2286 (5)	0.22091 (9)	0.0388 (8)
H4	−0.0832	−0.1295	0.1955	0.047*
C5	−0.04392 (10)	−0.4190 (5)	0.27219 (9)	0.0428 (8)
H5	−0.1033	−0.4500	0.2818	0.051*
C6	0.03101 (13)	−0.5640 (5)	0.30936 (8)	0.0428 (8)
H6	0.0229	−0.6941	0.3444	0.051*
C7	0.11784 (11)	−0.5186 (5)	0.29525 (9)	0.0442 (9)
H7	0.1690	−0.6177	0.3207	0.053*
C8	0.12973 (9)	−0.3283 (5)	0.24398 (9)	0.0365 (8)
H8	0.1891	−0.2973	0.2343	0.044*
C10	0.11906 (17)	0.3114 (7)	0.08632 (12)	0.0289 (7)
C11	0.02861 (19)	0.3590 (8)	0.07827 (13)	0.0341 (7)
H11	−0.0056	0.4953	0.0482	0.041*
C12	0.18829 (19)	0.4713 (8)	0.05463 (13)	0.0338 (7)
H12A	0.1577	0.6342	0.0273	0.041*
H12B	0.2360	0.5527	0.0910	0.041*
C15	0.33320 (17)	0.0634 (7)	−0.02953 (12)	0.0276 (7)
C16	0.41368 (18)	−0.0574 (8)	−0.04677 (13)	0.0365 (8)
H16	0.4729	−0.0091	−0.0222	0.044*
C17	0.40213 (19)	−0.2448 (8)	−0.09988 (13)	0.0375 (8)
H17	0.4547	−0.3306	−0.1122	0.045*
C18	0.3142 (2)	−0.3174 (9)	−0.13784 (14)	0.0429 (9)
H18	0.3096	−0.4504	−0.1744	0.051*
C19	0.23539 (19)	−0.1991 (8)	−0.12267 (13)	0.0409 (9)
H19	0.1767	−0.2456	−0.1484	0.049*
C20	0.24579 (17)	−0.0055 (7)	−0.06717 (12)	0.0293 (7)
C32	0.28777 (18)	0.1186 (7)	0.50472 (13)	0.0311 (7)
C33	0.22925 (12)	−0.0908 (4)	0.53084 (8)	0.0339 (7)
C34	0.24384 (13)	−0.1601 (5)	0.59954 (8)	0.0446 (9)
H34	0.2931	−0.0741	0.6302	0.054*
C35	0.18629 (15)	−0.3553 (5)	0.62338 (7)	0.0502 (9)
H35	0.1963	−0.4027	0.6703	0.060*
C36	0.11415 (14)	−0.4811 (5)	0.57853 (10)	0.0525 (10)
H36	0.0748	−0.6145	0.5948	0.063*
C37	0.09956 (12)	−0.4118 (5)	0.50984 (9)	0.0493 (9)
H37	0.0502	−0.4978	0.4792	0.059*
C38	0.15710 (13)	−0.2166 (5)	0.48599 (7)	0.0402 (8)
H38	0.1471	−0.1692	0.4390	0.048*
C40	0.35437 (17)	0.4084 (8)	0.44633 (13)	0.0301 (7)
C41	0.39498 (19)	0.4419 (8)	0.51185 (13)	0.0365 (8)
H41	0.4438	0.5709	0.5284	0.044*
C42	0.37294 (19)	0.5678 (8)	0.38533 (12)	0.0339 (7)
H42A	0.3168	0.6707	0.3631	0.041*
H42B	0.4214	0.7136	0.3998	0.041*
C45	0.39843 (17)	0.1057 (7)	0.25065 (13)	0.0289 (7)
C46	0.37797 (18)	−0.0470 (8)	0.18831 (13)	0.0347 (8)
H46	0.3214	−0.0214	0.1577	0.042*
C47	0.44326 (19)	−0.2325 (8)	0.17417 (13)	0.0371 (8)
H47	0.4317	−0.3381	0.1328	0.045*
C48	0.5284 (2)	−0.2719 (8)	0.21994 (13)	0.0390 (8)
H48	0.5717	−0.4050	0.2084	0.047*
C49	0.54947 (19)	−0.1230 (8)	0.28005 (13)	0.0359 (8)
H49	0.6067	−0.1478	0.3099	0.043*
C50	0.48256 (18)	0.0686 (7)	0.29570 (12)	0.0289 (7)
O1	−0.00585 (11)	0.1743 (5)	0.12147 (8)	0.0339 (5)
O31	0.35385 (12)	0.2580 (5)	0.55065 (8)	0.0370 (5)
N9	0.14449 (14)	0.0937 (6)	0.13455 (10)	0.0312 (6)
N13	0.23177 (14)	0.2829 (6)	0.01091 (10)	0.0297 (6)
N14	0.32274 (14)	0.2526 (6)	0.02065 (10)	0.0324 (6)
N21	0.18141 (15)	0.1361 (6)	−0.04007 (11)	0.0353 (7)
N39	0.28587 (15)	0.1994 (6)	0.44192 (10)	0.0316 (6)
N43	0.40198 (14)	0.3690 (6)	0.33659 (10)	0.0295 (6)
N44	0.34733 (14)	0.3007 (6)	0.27797 (10)	0.0323 (6)
N51	0.48369 (14)	0.2369 (6)	0.35103 (10)	0.0316 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0254 (14)	0.031 (2)	0.0306 (14)	0.0006 (13)	0.0058 (11)	−0.0050 (13)
C3	0.0315 (14)	0.032 (2)	0.0276 (13)	−0.0026 (14)	0.0091 (11)	−0.0060 (13)
C4	0.0351 (15)	0.039 (2)	0.0460 (16)	0.0047 (15)	0.0175 (13)	0.0017 (16)
C5	0.0453 (18)	0.045 (2)	0.0445 (16)	−0.0048 (17)	0.0237 (14)	−0.0016 (17)
C6	0.058 (2)	0.041 (2)	0.0314 (14)	−0.0082 (18)	0.0134 (14)	0.0012 (15)
C7	0.0414 (17)	0.052 (3)	0.0361 (16)	−0.0041 (17)	−0.0010 (13)	0.0039 (16)
C8	0.0362 (16)	0.041 (2)	0.0338 (14)	−0.0053 (15)	0.0099 (12)	−0.0031 (14)
C10	0.0310 (15)	0.030 (2)	0.0270 (13)	−0.0003 (14)	0.0086 (11)	−0.0068 (13)
C11	0.0368 (16)	0.038 (2)	0.0301 (13)	0.0038 (15)	0.0117 (11)	0.0022 (14)
C12	0.0383 (16)	0.027 (2)	0.0396 (15)	−0.0052 (15)	0.0166 (12)	−0.0043 (14)
C15	0.0295 (14)	0.0276 (19)	0.0266 (13)	−0.0030 (13)	0.0077 (11)	0.0028 (13)
C16	0.0268 (14)	0.046 (2)	0.0372 (15)	−0.0009 (15)	0.0063 (11)	0.0022 (15)
C17	0.0365 (16)	0.040 (2)	0.0407 (15)	0.0038 (16)	0.0182 (12)	0.0041 (16)
C18	0.0443 (18)	0.051 (3)	0.0368 (15)	−0.0085 (17)	0.0171 (13)	−0.0099 (15)
C19	0.0341 (16)	0.053 (3)	0.0375 (15)	−0.0121 (16)	0.0112 (12)	−0.0099 (16)
C20	0.0278 (14)	0.034 (2)	0.0287 (13)	−0.0053 (13)	0.0120 (11)	0.0008 (13)
C32	0.0321 (15)	0.028 (2)	0.0340 (14)	0.0076 (14)	0.0084 (12)	−0.0020 (13)
C33	0.0370 (16)	0.032 (2)	0.0370 (14)	0.0093 (15)	0.0179 (12)	0.0029 (14)
C34	0.0557 (19)	0.042 (3)	0.0400 (16)	0.0029 (18)	0.0196 (14)	0.0038 (16)
C35	0.066 (2)	0.047 (3)	0.0452 (17)	0.009 (2)	0.0301 (17)	0.0077 (17)
C36	0.058 (2)	0.039 (3)	0.073 (2)	0.0071 (18)	0.0421 (18)	0.0106 (19)
C37	0.0434 (18)	0.044 (3)	0.065 (2)	0.0016 (17)	0.0224 (16)	0.0014 (19)
C38	0.0408 (16)	0.038 (2)	0.0456 (16)	0.0040 (16)	0.0184 (13)	0.0029 (16)
C40	0.0254 (14)	0.031 (2)	0.0345 (15)	0.0036 (13)	0.0064 (11)	−0.0049 (13)
C41	0.0332 (15)	0.039 (2)	0.0384 (16)	−0.0007 (15)	0.0101 (12)	−0.0038 (15)
C42	0.0373 (16)	0.031 (2)	0.0346 (14)	0.0017 (15)	0.0099 (12)	0.0015 (14)
C45	0.0262 (14)	0.033 (2)	0.0297 (13)	0.0001 (14)	0.0111 (11)	0.0062 (13)
C46	0.0331 (15)	0.041 (2)	0.0313 (14)	−0.0033 (15)	0.0087 (12)	0.0036 (14)
C47	0.0421 (16)	0.043 (2)	0.0301 (13)	−0.0053 (17)	0.0154 (12)	−0.0013 (15)
C48	0.0434 (17)	0.040 (2)	0.0388 (15)	0.0059 (16)	0.0213 (13)	0.0069 (16)
C49	0.0341 (15)	0.042 (2)	0.0330 (14)	0.0048 (15)	0.0098 (12)	0.0063 (15)
C50	0.0292 (14)	0.0314 (19)	0.0276 (13)	−0.0003 (14)	0.0096 (11)	0.0071 (13)
O1	0.0243 (10)	0.0412 (16)	0.0376 (10)	0.0033 (9)	0.0099 (8)	0.0029 (10)
O31	0.0407 (11)	0.0414 (15)	0.0288 (9)	0.0010 (11)	0.0067 (8)	−0.0010 (10)
N9	0.0256 (11)	0.0378 (18)	0.0312 (12)	0.0016 (12)	0.0079 (9)	−0.0030 (12)
N13	0.0305 (12)	0.0317 (17)	0.0291 (11)	−0.0044 (12)	0.0117 (9)	−0.0013 (11)
N14	0.0279 (12)	0.0392 (18)	0.0309 (11)	−0.0016 (12)	0.0074 (9)	0.0018 (12)
N21	0.0292 (12)	0.042 (2)	0.0362 (12)	−0.0055 (12)	0.0107 (10)	−0.0055 (12)
N39	0.0330 (13)	0.0344 (18)	0.0283 (11)	0.0033 (12)	0.0079 (9)	−0.0016 (11)
N43	0.0293 (12)	0.0318 (17)	0.0288 (11)	0.0019 (11)	0.0090 (9)	0.0036 (11)
N44	0.0273 (12)	0.0398 (19)	0.0297 (11)	−0.0029 (12)	0.0049 (9)	0.0046 (11)
N51	0.0316 (12)	0.0348 (17)	0.0289 (11)	0.0045 (12)	0.0072 (9)	0.0039 (12)

Geometric parameters (Å, º) top

C2—N9	1.303 (3)	C32—C33	1.464 (3)
C2—O1	1.365 (3)	C33—C34	1.390
C2—C3	1.470 (3)	C33—C38	1.390
C3—C4	1.390	C34—C35	1.390
C3—C8	1.390	C34—H34	0.950
C4—C5	1.390	C35—C36	1.390
C4—H4	0.950	C35—H35	0.950
C5—C6	1.390	C36—C37	1.390
C5—H5	0.950	C36—H36	0.950
C6—C7	1.390	C37—C38	1.390
C6—H6	0.950	C37—H37	0.950
C7—C8	1.390	C38—H38	0.950
C7—H7	0.950	C40—C41	1.346 (4)
C8—H8	0.950	C40—N39	1.395 (4)
C10—C11	1.343 (4)	C40—C42	1.498 (4)
C10—N9	1.397 (4)	C41—O31	1.372 (4)
C10—C12	1.504 (4)	C41—H41	0.950
C11—O1	1.382 (3)	C42—N43	1.465 (4)
C11—H11	0.950	C42—H42A	0.990
C12—N13	1.470 (4)	C42—H42B	0.990
C12—H12A	0.990	C45—N44	1.360 (4)
C12—H12B	0.990	C45—C50	1.408 (4)
C15—N14	1.364 (4)	C45—C46	1.417 (4)
C15—C20	1.410 (4)	C46—C47	1.366 (4)
C15—C16	1.422 (4)	C46—H46	0.950
C16—C17	1.358 (4)	C47—C48	1.428 (4)
C16—H16	0.950	C47—H47	0.950
C17—C18	1.423 (4)	C48—C49	1.371 (4)
C17—H17	0.950	C48—H48	0.950
C18—C19	1.379 (4)	C49—C50	1.412 (4)
C18—H18	0.950	C49—H49	0.950
C19—C20	1.413 (4)	C50—N51	1.352 (4)
C19—H19	0.950	N13—N21	1.332 (3)
C20—N21	1.356 (4)	N13—N14	1.338 (3)
C32—N39	1.308 (3)	N43—N44	1.333 (3)
C32—O31	1.373 (3)	N43—N51	1.342 (3)

N9—C2—O1	113.7 (3)	C35—C34—H34	120.0
N9—C2—C3	128.7 (2)	C33—C34—H34	120.0
O1—C2—C3	117.6 (2)	C36—C35—C34	120.0
C4—C3—C8	120.0	C36—C35—H35	120.0
C4—C3—C2	120.50 (15)	C34—C35—H35	120.0
C8—C3—C2	119.47 (15)	C35—C36—C37	120.0
C5—C4—C3	120.0	C35—C36—H36	120.0
C5—C4—H4	120.0	C37—C36—H36	120.0
C3—C4—H4	120.0	C38—C37—C36	120.0
C4—C5—C6	120.0	C38—C37—H37	120.0
C4—C5—H5	120.0	C36—C37—H37	120.0
C6—C5—H5	120.0	C37—C38—C33	120.0
C7—C6—C5	120.0	C37—C38—H38	120.0
C7—C6—H6	120.0	C33—C38—H38	120.0
C5—C6—H6	120.0	C41—C40—N39	109.2 (3)
C8—C7—C6	120.0	C41—C40—C42	128.4 (3)
C8—C7—H7	120.0	N39—C40—C42	122.4 (2)
C6—C7—H7	120.0	C40—C41—O31	108.4 (3)
C7—C8—C3	120.0	C40—C41—H41	125.8
C7—C8—H8	120.0	O31—C41—H41	125.8
C3—C8—H8	120.0	N43—C42—C40	111.0 (3)
C11—C10—N9	109.6 (2)	N43—C42—H42A	109.4
C11—C10—C12	128.3 (3)	C40—C42—H42A	109.4
N9—C10—C12	122.0 (2)	N43—C42—H42B	109.4
C10—C11—O1	107.8 (3)	C40—C42—H42B	109.4
C10—C11—H11	126.1	H42A—C42—H42B	108.0
O1—C11—H11	126.1	N44—C45—C50	108.6 (2)
N13—C12—C10	112.0 (3)	N44—C45—C46	130.0 (2)
N13—C12—H12A	109.2	C50—C45—C46	121.4 (3)
C10—C12—H12A	109.2	C47—C46—C45	117.0 (2)
N13—C12—H12B	109.2	C47—C46—H46	121.5
C10—C12—H12B	109.2	C45—C46—H46	121.5
H12A—C12—H12B	107.9	C46—C47—C48	121.8 (3)
N14—C15—C20	108.4 (2)	C46—C47—H47	119.1
N14—C15—C16	130.6 (2)	C48—C47—H47	119.1
C20—C15—C16	121.0 (3)	C49—C48—C47	121.8 (3)
C17—C16—C15	117.0 (3)	C49—C48—H48	119.1
C17—C16—H16	121.5	C47—C48—H48	119.1
C15—C16—H16	121.5	C48—C49—C50	117.2 (3)
C16—C17—C18	122.4 (3)	C48—C49—H49	121.4
C16—C17—H17	118.8	C50—C49—H49	121.4
C18—C17—H17	118.8	N51—C50—C45	109.1 (2)
C19—C18—C17	121.5 (3)	N51—C50—C49	130.1 (2)
C19—C18—H18	119.3	C45—C50—C49	120.8 (3)
C17—C18—H18	119.3	C2—O1—C11	104.5 (2)
C18—C19—C20	117.0 (3)	C41—O31—C32	104.5 (2)
C18—C19—H19	121.5	C2—N9—C10	104.5 (2)
C20—C19—H19	121.5	N21—N13—N14	117.7 (2)
N21—C20—C15	109.1 (2)	N21—N13—C12	120.8 (2)
N21—C20—C19	129.9 (2)	N14—N13—C12	121.5 (2)
C15—C20—C19	121.1 (2)	N13—N14—C15	102.3 (2)
N39—C32—O31	113.1 (3)	N13—N21—C20	102.5 (2)
N39—C32—C33	128.9 (2)	C32—N39—C40	104.8 (2)
O31—C32—C33	118.0 (2)	N44—N43—N51	117.3 (2)
C34—C33—C38	120.0	N44—N43—C42	121.9 (2)
C34—C33—C32	121.02 (16)	N51—N43—C42	120.8 (2)
C38—C33—C32	118.97 (15)	N43—N44—C45	102.6 (2)
C35—C34—C33	120.0	N43—N51—C50	102.5 (2)

N9—C2—C3—C4	179.9 (2)	C50—C45—C46—C47	0.4 (4)
O1—C2—C3—C4	1.7 (3)	C45—C46—C47—C48	0.0 (5)
N9—C2—C3—C8	1.8 (4)	C46—C47—C48—C49	−0.8 (5)
O1—C2—C3—C8	−176.40 (18)	C47—C48—C49—C50	1.1 (5)
C8—C3—C4—C5	0.0	N44—C45—C50—N51	0.6 (3)
C2—C3—C4—C5	−178.1 (2)	C46—C45—C50—N51	−179.5 (3)
C3—C4—C5—C6	0.0	N44—C45—C50—C49	−180.0 (3)
C4—C5—C6—C7	0.0	C46—C45—C50—C49	0.0 (4)
C5—C6—C7—C8	0.0	C48—C49—C50—N51	178.6 (3)
C6—C7—C8—C3	0.0	C48—C49—C50—C45	−0.7 (4)
C4—C3—C8—C7	0.0	N9—C2—O1—C11	−1.4 (3)
C2—C3—C8—C7	178.1 (2)	C3—C2—O1—C11	177.1 (2)
N9—C10—C11—O1	0.4 (3)	C10—C11—O1—C2	0.5 (3)
C12—C10—C11—O1	−175.3 (3)	C40—C41—O31—C32	−0.2 (3)
C11—C10—C12—N13	−117.7 (3)	N39—C32—O31—C41	0.6 (3)
N9—C10—C12—N13	67.2 (3)	C33—C32—O31—C41	−178.5 (2)
N14—C15—C16—C17	179.4 (3)	O1—C2—N9—C10	1.6 (3)
C20—C15—C16—C17	−1.3 (5)	C3—C2—N9—C10	−176.7 (3)
C15—C16—C17—C18	0.8 (5)	C11—C10—N9—C2	−1.2 (3)
C16—C17—C18—C19	0.3 (5)	C12—C10—N9—C2	174.8 (3)
C17—C18—C19—C20	−0.8 (5)	C10—C12—N13—N21	55.7 (3)
N14—C15—C20—N21	−0.9 (3)	C10—C12—N13—N14	−124.4 (3)
C16—C15—C20—N21	179.6 (3)	N21—N13—N14—C15	−0.2 (3)
N14—C15—C20—C19	−179.8 (3)	C12—N13—N14—C15	179.8 (2)
C16—C15—C20—C19	0.7 (5)	C20—C15—N14—N13	0.7 (3)
C18—C19—C20—N21	−178.3 (3)	C16—C15—N14—N13	−179.9 (3)
C18—C19—C20—C15	0.3 (5)	N14—N13—N21—C20	−0.3 (3)
N39—C32—C33—C34	177.1 (2)	C12—N13—N21—C20	179.7 (2)
O31—C32—C33—C34	−4.0 (3)	C15—C20—N21—N13	0.7 (3)
N39—C32—C33—C38	−4.2 (4)	C19—C20—N21—N13	179.5 (3)
O31—C32—C33—C38	174.7 (2)	O31—C32—N39—C40	−0.7 (3)
C38—C33—C34—C35	0.0	C33—C32—N39—C40	178.3 (3)
C32—C33—C34—C35	178.7 (2)	C41—C40—N39—C32	0.5 (3)
C33—C34—C35—C36	0.0	C42—C40—N39—C32	−177.5 (3)
C34—C35—C36—C37	0.0	C40—C42—N43—N44	107.4 (3)
C35—C36—C37—C38	0.0	C40—C42—N43—N51	−69.3 (3)
C36—C37—C38—C33	0.0	N51—N43—N44—C45	−0.6 (3)
C34—C33—C38—C37	0.0	C42—N43—N44—C45	−177.4 (3)
C32—C33—C38—C37	−178.8 (2)	C50—C45—N44—N43	0.0 (3)
N39—C40—C41—O31	−0.2 (3)	C46—C45—N44—N43	−180.0 (3)
C42—C40—C41—O31	177.7 (3)	N44—N43—N51—C50	0.9 (3)
C41—C40—C42—N43	120.0 (3)	C42—N43—N51—C50	177.8 (2)
N39—C40—C42—N43	−62.4 (3)	C45—C50—N51—N43	−0.8 (3)
N44—C45—C46—C47	−179.7 (3)	C49—C50—N51—N43	179.8 (3)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₄O
M_r	276.30
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	180
a, b, c (Å)	14.880 (2), 4.6251 (5), 20.043 (3)
β (°)	100.963 (19)
V (Å³)	1354.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.52 × 0.24 × 0.12

Data collection
Diffractometer	Stoe IPDS diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9269, 2943, 2202
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.082, 0.95
No. of reflections	2943
No. of parameters	356
No. of restraints	1
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: IPDS2.87 (Stoe & Cie, 1997), IPDS2.87, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), OPTEP-3 (Farrugia, 1997), SHELXL97.

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