A second polymorph of 2,4,6-tris­(3,5-dimethyl-1H-pyrazol-1-yl)-1,3,5-triazine

Ng, S.W.

doi:10.1107/S1600536812043255

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3201

doi:10.1107/S1600536812043255

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A second polymorph of 2,4,6-tris(3,5-dimethyl-1H-pyrazol-1-yl)-1,3,5-triazine

Seik Weng Ng ^a,^b ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 13 October 2012; accepted 17 October 2012; online 24 October 2012)

The molecule of the title compound, C₁₈H₂₁N₉, is nearly planar, with the three pyrazole rings aligned at 2.40 (5), 9.27 (5) and 9.71 (5)° with respect to the triazine ring. The triazine ring is planar (r.m.s. deviation = 0.005 Å), the distortion from a hexagonal arrangement arising from the angles at the N [112.4 (1)–113.1 (1)°] and C [127.1 (1)–127.6 (1)°] atoms deviating from 120°. The crystal studied was an inversion twin.

Related literature

For another Pna2₁ polymorph, see: Guerrero et al. (2003 ). For a discussion of the determination of the absolute parameter, see: Flack & Bernardinelli (2000 ); Hooft et al. (2008 ); Spek (2009 ).

Experimental

Crystal data

C₁₈H₂₁N₉
M_r = 363.44
Orthorhombic, P n a 2₁
a = 7.1840 (1) Å
b = 12.5079 (1) Å
c = 19.9527 (1) Å
V = 1792.89 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.71 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas CCD detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.815, T_max = 0.871
33189 measured reflections
3744 independent reflections
3740 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.079
S = 1.06
3744 reflections
250 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1813 Friedel pairs
Flack parameter: 0.51 (19)

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812043255/zs2237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043255/zs2237Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812043255/zs2237Isup3.cml

checkCIF report

Comment top

Tris(3,5-dimethylpyrazol-1-yl)-1,3,5-triazine (Scheme I) was reported as being orthorhombic in the Pna2₁ space group [7.941 (1), 12.555 (1), 18.901 (1) Å] (Guerrero et al., 2003). For organic compounds belonging to noncentrosymmetric space groups, Friedel pairs are generally merged so that the absolute structure is not determined, particularly if the diffractometer measurements are of average quality.

A different polymorph that belongs to the same space group has been found in the present study. Because the diffraction measurements are of exceptionally high quality, the Flack parameter (Flack, 1983) could be refined. As this parameter refined to 0.5 (2), the structure (Fig. 1) is then interpreted as being a racemic twin. The somewhat more reliable Hooft value of 0.48 (3), with the smaller standard uncertainty, indicates that the absolute structure had probably been determined correctly.

The molecule of the title compound is nearly planar with the three pyrazole rings aligned at 2.40 (5), 9.27 (5) and 9.71 (5)° with respect to the triazine ring. The triazine ring is planar (r.m.s. deviation 0.005Å), the distortion from a hexagonal arrangement arising from the angles at the nitrogen [112.4 (1) to 113.1 (1) °] and carbon [127.1 (1) to 127.6 (1)°] atoms deviating from 120°.

Related literature top

For another Pna2₁ polymorph, see: Guerrero et al. (2003). For a discussion of the determination of the absolute parameter, see: Flack & Bernardinelli (2000); Hooft et al. (2008); Spek (2009).

Experimental top

3,5-Dimethylpyrazole (0.77 g, 8 mmol) and sodium hydride (0.38 g, 16 mmol) were added to a solution of cyanuric chloride (0.74 g, 4 mmol) dissolved in dry THF (40 ml). The mixture was stirred for 20 h. The THF was removed under reduced pressure and water was added. The organic compound was extracted with dichloromethane (3 × 15 ml). The organic layer was dried over magnesium sulfate. The solvent was evaporated and the product purified on silica gel. Colorless crystals were obtained upon recrystalization from a hexane-dichloromethane (1:1) mixture in 60% yield.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₈H₂₁N₉ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

2,4,6-Tris(3,5-dimethyl-1H-pyrazol-1-yl)-1,3,5-triazine top

Crystal data top

C₁₈H₂₁N₉	F(000) = 768
M_r = 363.44	D_x = 1.347 Mg m⁻³
Orthorhombic, Pna2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2c -2n	Cell parameters from 23687 reflections
a = 7.1840 (1) Å	θ = 3.5–76.5°
b = 12.5079 (1) Å	µ = 0.71 mm⁻¹
c = 19.9527 (1) Å	T = 100 K
V = 1792.89 (3) Å³	Prism, colorless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas CCD detector	3744 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3740 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.016
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.7°, θ_min = 4.2°
ω scans	h = −9→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −15→15
T_min = 0.815, T_max = 0.871	l = −25→25
33189 measured 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)] = 0.028	H-atom parameters constrained
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0643P)² + 0.1472P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3744 reflections	Δρ_max = 0.17 e Å⁻³
250 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1813 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.51 (19)

Crystal data top

C₁₈H₂₁N₉	V = 1792.89 (3) Å³
M_r = 363.44	Z = 4
Orthorhombic, Pna2₁	Cu Kα radiation
a = 7.1840 (1) Å	µ = 0.71 mm⁻¹
b = 12.5079 (1) Å	T = 100 K
c = 19.9527 (1) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas CCD detector	3744 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3740 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.871	R_int = 0.016
33189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.079	Δρ_max = 0.17 e Å⁻³
S = 1.06	Δρ_min = −0.23 e Å⁻³
3744 reflections	Absolute structure: Flack (1983), 1813 Friedel pairs
250 parameters	Absolute structure parameter: 0.51 (19)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.64690 (14)	0.33516 (7)	0.49998 (4)	0.01670 (18)
N2	0.76115 (13)	0.35089 (7)	0.61216 (5)	0.01684 (18)
N3	0.70433 (13)	0.50706 (7)	0.54716 (5)	0.01692 (19)
N4	0.70786 (13)	0.18485 (7)	0.56534 (4)	0.01575 (19)
N5	0.65449 (13)	0.12198 (8)	0.51162 (5)	0.01787 (19)
N6	0.58836 (13)	0.49074 (7)	0.43969 (4)	0.01651 (19)
N7	0.60689 (13)	0.60069 (7)	0.43401 (5)	0.01858 (19)
N8	0.81077 (13)	0.52146 (7)	0.65568 (4)	0.01588 (18)
N9	0.89652 (12)	0.47659 (7)	0.71095 (5)	0.01760 (19)
C1	0.70516 (15)	0.29617 (8)	0.55866 (6)	0.0150 (2)
C2	0.75663 (14)	0.45598 (9)	0.60231 (5)	0.0154 (2)
C3	0.64950 (15)	0.44148 (8)	0.49846 (5)	0.0153 (2)
C4	0.82309 (17)	0.16382 (9)	0.68709 (5)	0.0204 (2)
H4A	0.8586	0.1033	0.7155	0.031*
H4B	0.7198	0.2026	0.7080	0.031*
H4C	0.9297	0.2119	0.6818	0.031*
C5	0.76404 (15)	0.12363 (9)	0.62003 (6)	0.0170 (2)
C6	0.74711 (16)	0.01995 (9)	0.59952 (6)	0.0194 (2)
H6	0.7756	−0.0421	0.6250	0.023*
C7	0.67861 (14)	0.02291 (9)	0.53266 (6)	0.0176 (2)
C8	0.63441 (17)	−0.07007 (9)	0.48831 (6)	0.0212 (2)
H8A	0.6041	−0.0442	0.4432	0.032*
H8B	0.5277	−0.1092	0.5066	0.032*
H8C	0.7424	−0.1178	0.4860	0.032*
C9	0.44991 (16)	0.33159 (9)	0.37583 (6)	0.0205 (2)
H9A	0.3880	0.3215	0.3325	0.031*
H9B	0.3669	0.3082	0.4119	0.031*
H9C	0.5646	0.2892	0.3770	0.031*
C10	0.49607 (15)	0.44699 (9)	0.38503 (5)	0.0170 (2)
C11	0.45694 (16)	0.53202 (9)	0.34406 (6)	0.0194 (2)
H11	0.3947	0.5295	0.3021	0.023*
C12	0.52746 (15)	0.62463 (9)	0.37652 (6)	0.0191 (2)
C13	0.51606 (18)	0.73881 (10)	0.35422 (7)	0.0257 (2)
H13A	0.6340	0.7750	0.3640	0.039*
H13B	0.4147	0.7748	0.3782	0.039*
H13C	0.4920	0.7414	0.3059	0.039*
C14	0.71358 (17)	0.70472 (9)	0.60992 (6)	0.0230 (2)
H14A	0.7102	0.7776	0.6280	0.035*
H14B	0.5864	0.6805	0.6007	0.035*
H14C	0.7862	0.7039	0.5683	0.035*
C15	0.80173 (15)	0.63183 (8)	0.65987 (6)	0.0179 (2)
C16	0.88424 (16)	0.65728 (9)	0.71970 (6)	0.0204 (2)
H16	0.9001	0.7269	0.7379	0.024*
C17	0.94152 (15)	0.55897 (9)	0.74920 (5)	0.0180 (2)
C18	1.03930 (18)	0.54346 (9)	0.81452 (6)	0.0236 (2)
H18A	1.0544	0.4668	0.8232	0.035*
H18B	0.9657	0.5758	0.8506	0.035*
H18C	1.1620	0.5776	0.8126	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0178 (4)	0.0167 (4)	0.0155 (4)	−0.0006 (3)	−0.0008 (3)	0.0003 (3)
N2	0.0178 (4)	0.0169 (4)	0.0158 (4)	−0.0008 (3)	0.0006 (3)	0.0006 (3)
N3	0.0182 (4)	0.0165 (4)	0.0160 (5)	−0.0006 (3)	−0.0001 (3)	−0.0009 (3)
N4	0.0180 (4)	0.0157 (4)	0.0136 (4)	−0.0008 (3)	−0.0008 (3)	−0.0003 (3)
N5	0.0201 (4)	0.0171 (4)	0.0164 (4)	−0.0021 (3)	0.0009 (3)	−0.0022 (3)
N6	0.0182 (4)	0.0155 (4)	0.0158 (4)	−0.0013 (3)	−0.0010 (4)	0.0012 (4)
N7	0.0214 (4)	0.0147 (4)	0.0197 (4)	−0.0003 (3)	−0.0001 (4)	0.0027 (3)
N8	0.0181 (4)	0.0148 (4)	0.0147 (4)	−0.0004 (3)	−0.0004 (3)	−0.0007 (3)
N9	0.0193 (4)	0.0204 (4)	0.0131 (4)	0.0001 (3)	−0.0001 (3)	0.0004 (3)
C1	0.0140 (4)	0.0154 (5)	0.0156 (4)	−0.0014 (4)	0.0021 (3)	0.0006 (4)
C2	0.0135 (5)	0.0183 (5)	0.0144 (5)	−0.0017 (4)	0.0017 (4)	−0.0012 (4)
C3	0.0139 (4)	0.0173 (5)	0.0146 (5)	−0.0013 (4)	0.0006 (3)	0.0008 (4)
C4	0.0241 (5)	0.0214 (5)	0.0157 (5)	0.0016 (4)	−0.0032 (4)	0.0014 (4)
C5	0.0163 (5)	0.0176 (5)	0.0171 (5)	0.0007 (4)	0.0023 (4)	0.0022 (4)
C6	0.0216 (5)	0.0170 (5)	0.0195 (5)	0.0008 (4)	0.0015 (4)	0.0022 (4)
C7	0.0171 (4)	0.0181 (5)	0.0178 (5)	−0.0013 (4)	0.0037 (4)	−0.0009 (4)
C8	0.0273 (6)	0.0170 (5)	0.0193 (5)	−0.0016 (4)	0.0035 (4)	−0.0027 (4)
C9	0.0238 (5)	0.0212 (5)	0.0166 (5)	−0.0024 (4)	−0.0019 (4)	−0.0013 (4)
C10	0.0149 (5)	0.0222 (5)	0.0138 (5)	0.0001 (4)	0.0004 (4)	0.0003 (4)
C11	0.0168 (5)	0.0250 (5)	0.0164 (5)	−0.0004 (4)	0.0002 (4)	0.0020 (4)
C12	0.0161 (5)	0.0200 (5)	0.0212 (5)	0.0007 (4)	0.0019 (4)	0.0049 (4)
C13	0.0241 (6)	0.0219 (5)	0.0313 (6)	0.0020 (4)	−0.0015 (5)	0.0098 (4)
C14	0.0300 (6)	0.0173 (5)	0.0219 (5)	0.0023 (4)	−0.0041 (5)	−0.0005 (4)
C15	0.0196 (5)	0.0171 (5)	0.0168 (5)	−0.0014 (4)	0.0019 (4)	−0.0009 (4)
C16	0.0246 (5)	0.0191 (5)	0.0176 (5)	−0.0019 (4)	0.0004 (4)	−0.0031 (4)
C17	0.0176 (5)	0.0213 (5)	0.0151 (5)	−0.0020 (4)	0.0014 (4)	−0.0012 (4)
C18	0.0285 (6)	0.0250 (5)	0.0175 (5)	−0.0007 (5)	−0.0052 (5)	−0.0018 (4)

Geometric parameters (Å, º) top

N1—C3	1.3303 (13)	C8—H8A	0.9800
N1—C1	1.3356 (14)	C8—H8B	0.9800
N2—C2	1.3295 (14)	C8—H8C	0.9800
N2—C1	1.3302 (14)	C9—C10	1.4923 (15)
N3—C2	1.3268 (14)	C9—H9A	0.9800
N3—C3	1.3312 (14)	C9—H9B	0.9800
N4—N5	1.3836 (13)	C9—H9C	0.9800
N4—C5	1.3929 (14)	C10—C11	1.3705 (15)
N4—C1	1.3989 (13)	C11—C12	1.4206 (16)
N5—C7	1.3197 (14)	C11—H11	0.9500
N6—N7	1.3863 (11)	C12—C13	1.4980 (14)
N6—C10	1.3887 (14)	C13—H13A	0.9800
N6—C3	1.3957 (13)	C13—H13B	0.9800
N7—C12	1.3157 (15)	C13—H13C	0.9800
N8—N9	1.3822 (12)	C14—C15	1.4918 (15)
N8—C15	1.3846 (13)	C14—H14A	0.9800
N8—C2	1.3985 (13)	C14—H14B	0.9800
N9—C17	1.3225 (14)	C14—H14C	0.9800
C4—C5	1.4909 (15)	C15—C16	1.3703 (15)
C4—H4A	0.9800	C16—C17	1.4240 (15)
C4—H4B	0.9800	C16—H16	0.9500
C4—H4C	0.9800	C17—C18	1.4931 (15)
C5—C6	1.3653 (15)	C18—H18A	0.9800
C6—C7	1.4225 (16)	C18—H18B	0.9800
C6—H6	0.9500	C18—H18C	0.9800
C7—C8	1.4954 (15)

C3—N1—C1	112.37 (9)	H8B—C8—H8C	109.5
C2—N2—C1	112.51 (9)	C10—C9—H9A	109.5
C2—N3—C3	113.11 (9)	C10—C9—H9B	109.5
N5—N4—C5	112.01 (9)	H9A—C9—H9B	109.5
N5—N4—C1	119.22 (9)	C10—C9—H9C	109.5
C5—N4—C1	128.74 (10)	H9A—C9—H9C	109.5
C7—N5—N4	104.53 (9)	H9B—C9—H9C	109.5
N7—N6—C10	111.88 (8)	C11—C10—N6	105.10 (9)
N7—N6—C3	118.44 (9)	C11—C10—C9	129.18 (11)
C10—N6—C3	129.51 (9)	N6—C10—C9	125.72 (9)
C12—N7—N6	104.79 (9)	C10—C11—C12	106.73 (10)
N9—N8—C15	112.18 (8)	C10—C11—H11	126.6
N9—N8—C2	119.58 (8)	C12—C11—H11	126.6
C15—N8—C2	128.08 (9)	N7—C12—C11	111.50 (10)
C17—N9—N8	104.65 (9)	N7—C12—C13	119.98 (10)
N2—C1—N1	127.61 (10)	C11—C12—C13	128.49 (11)
N2—C1—N4	115.56 (10)	C12—C13—H13A	109.5
N1—C1—N4	116.83 (9)	C12—C13—H13B	109.5
N3—C2—N2	127.27 (10)	H13A—C13—H13B	109.5
N3—C2—N8	115.36 (9)	C12—C13—H13C	109.5
N2—C2—N8	117.37 (9)	H13A—C13—H13C	109.5
N1—C3—N3	127.12 (10)	H13B—C13—H13C	109.5
N1—C3—N6	117.13 (9)	C15—C14—H14A	109.5
N3—C3—N6	115.75 (9)	C15—C14—H14B	109.5
C5—C4—H4A	109.5	H14A—C14—H14B	109.5
C5—C4—H4B	109.5	C15—C14—H14C	109.5
H4A—C4—H4B	109.5	H14A—C14—H14C	109.5
C5—C4—H4C	109.5	H14B—C14—H14C	109.5
H4A—C4—H4C	109.5	C16—C15—N8	105.30 (9)
H4B—C4—H4C	109.5	C16—C15—C14	128.59 (10)
C6—C5—N4	105.16 (10)	N8—C15—C14	126.08 (10)
C6—C5—C4	127.92 (11)	C15—C16—C17	106.53 (10)
N4—C5—C4	126.89 (10)	C15—C16—H16	126.7
C5—C6—C7	106.69 (10)	C17—C16—H16	126.7
C5—C6—H6	126.7	N9—C17—C16	111.33 (10)
C7—C6—H6	126.7	N9—C17—C18	121.16 (10)
N5—C7—C6	111.60 (10)	C16—C17—C18	127.51 (10)
N5—C7—C8	120.94 (10)	C17—C18—H18A	109.5
C6—C7—C8	127.46 (10)	C17—C18—H18B	109.5
C7—C8—H8A	109.5	H18A—C18—H18B	109.5
C7—C8—H8B	109.5	C17—C18—H18C	109.5
H8A—C8—H8B	109.5	H18A—C18—H18C	109.5
C7—C8—H8C	109.5	H18B—C18—H18C	109.5
H8A—C8—H8C	109.5

C5—N4—N5—C7	−0.42 (12)	N5—N4—C5—C6	0.66 (12)
C1—N4—N5—C7	177.77 (9)	C1—N4—C5—C6	−177.31 (10)
C10—N6—N7—C12	−0.13 (11)	N5—N4—C5—C4	−177.36 (10)
C3—N6—N7—C12	−175.89 (9)	C1—N4—C5—C4	4.66 (18)
C15—N8—N9—C17	−0.33 (11)	N4—C5—C6—C7	−0.62 (11)
C2—N8—N9—C17	175.53 (9)	C4—C5—C6—C7	177.38 (11)
C2—N2—C1—N1	−0.66 (16)	N4—N5—C7—C6	0.01 (11)
C2—N2—C1—N4	179.50 (9)	N4—N5—C7—C8	179.63 (9)
C3—N1—C1—N2	0.23 (16)	C5—C6—C7—N5	0.40 (12)
C3—N1—C1—N4	−179.92 (9)	C5—C6—C7—C8	−179.20 (11)
N5—N4—C1—N2	−178.99 (9)	N7—N6—C10—C11	0.30 (12)
C5—N4—C1—N2	−1.14 (16)	C3—N6—C10—C11	175.47 (10)
N5—N4—C1—N1	1.15 (14)	N7—N6—C10—C9	−178.78 (10)
C5—N4—C1—N1	179.00 (10)	C3—N6—C10—C9	−3.62 (18)
C3—N3—C2—N2	0.98 (15)	N6—C10—C11—C12	−0.34 (12)
C3—N3—C2—N8	−178.34 (9)	C9—C10—C11—C12	178.70 (11)
C1—N2—C2—N3	−0.01 (15)	N6—N7—C12—C11	−0.09 (12)
C1—N2—C2—N8	179.29 (9)	N6—N7—C12—C13	178.25 (10)
N9—N8—C2—N3	−169.23 (9)	C10—C11—C12—N7	0.28 (13)
C15—N8—C2—N3	5.90 (15)	C10—C11—C12—C13	−177.89 (11)
N9—N8—C2—N2	11.38 (14)	N9—N8—C15—C16	−0.05 (11)
C15—N8—C2—N2	−173.49 (10)	C2—N8—C15—C16	−175.48 (10)
C1—N1—C3—N3	0.97 (15)	N9—N8—C15—C14	−178.12 (10)
C1—N1—C3—N6	−179.01 (9)	C2—N8—C15—C14	6.46 (17)
C2—N3—C3—N1	−1.51 (15)	N8—C15—C16—C17	0.39 (12)
C2—N3—C3—N6	178.46 (9)	C14—C15—C16—C17	178.39 (11)
N7—N6—C3—N1	−173.61 (9)	N8—N9—C17—C16	0.58 (11)
C10—N6—C3—N1	11.49 (16)	N8—N9—C17—C18	−179.66 (10)
N7—N6—C3—N3	6.41 (14)	C15—C16—C17—N9	−0.64 (13)
C10—N6—C3—N3	−168.49 (10)	C15—C16—C17—C18	179.63 (11)

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₉
M_r	363.44
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	7.1840 (1), 12.5079 (1), 19.9527 (1)
V (Å³)	1792.89 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas CCD detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.815, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	33189, 3744, 3740
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.079, 1.06
No. of reflections	3744
No. of parameters	250
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23
Absolute structure	Flack (1983), 1813 Friedel pairs
Absolute structure parameter	0.51 (19)

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

The author thanks the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

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