5,5-Dimethyl-2,2-bis­(pyridin-2-yl)-1,3-diazinane

Warad, I.; Alruwaili, A.; Al-Resayes, S.I.; Choudhary, M.I.; Yousuf, S.

doi:10.1107/S1600536812021629

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1786

doi:10.1107/S1600536812021629

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5,5-Dimethyl-2,2-bis(pyridin-2-yl)-1,3-diazinane

Ismail Warad,^a Afaf Alruwaili,^b Saud I. Al-Resayes,^a M. Iqbal Choudhary ^c,^a and Sammer Yousuf ^c ^*

^aDepartment of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, College of Science, University of Hail, PO Box 2440, Hail, Saudi Arabia, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 8 April 2012; accepted 13 May 2012; online 19 May 2012)

In the molecule of the title compound, C₁₆H₂₀N₄, the 1,3-diazinane ring adopts a chair conformation and the dihedral angle formed by the pyridine rings is 78.64 (8)°. The molecular conformation is stabilized by an intramolecular C—H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, centrosymmetrically related molecules are linked into dimers by pairs of N—H⋯N hydrogen bonds, generating rings of R₂²(10) graph-set motif.

Related literature

For the structures of related hexahydropyrimidines, see: Al-Resayes (2009 ); Song et al. (2010 ); Jayaratna & Norman (2010 ); Fun & Kia (2008 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₂₀N₄
M_r = 268.36
Triclinic, $[P \overline 1]$
a = 8.5535 (7) Å
b = 8.7124 (8) Å
c = 11.7241 (10) Å
α = 109.824 (2)°
β = 96.444 (2)°
γ = 109.658 (2)°
V = 748.33 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.48 × 0.42 × 0.39 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.966, T_max = 0.972
8514 measured reflections
2794 independent reflections
2422 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.05
2794 reflections
191 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N2ⁱ	0.882 (15)	2.469 (15)	3.2048 (14)	141.3 (13)
C4—H4B⋯N2	0.93	2.55	3.187 (2)	126
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021629/rz2740sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021629/rz2740Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021629/rz2740Isup3.cml

checkCIF report

Comment top

Condensation of 1,3-diamines with aldehydes and ketones is a well documented reaction for two potential products, classical Schiff bases and hexahydropyrimidine compounds (Al-Resayes, 2009; Song et al., 2010; Jayaratna, & Norman, 2010; Fun & Kia, 2008). Both of these products are extensively utilized as polydentate ligands to synthesize metal coordination complexes. The title compound was obtained during our attempt to synthesize novel ligands in order to study the coordination chemistry of targeted metals.

In the structure of the title compound (Fig. 1), the two pyridine (N1/C1–C5 and N2/C7–C11) rings are equatorially and axially orientated, respectively, with a dihedral angle of 78.64 (8)° between them. The six membered hexahydropyrimidine ring (N3/N4/C6/C12–C14) adopts a chair conformation, with puckering parameters Q = 0.5384 (14) Å, θ = 5.57 (15)° and ϕ = 179.9 (15)°. All bond lengths (Allen et al., 1987) and angles are in normal range. The molecular conformation is stabilized by a C4—H4B···N2 intramolecular hydrogen bond (Table 1). In the crystal structure, centrosymmetrically related molecules dimerize via pairs of N4—H4A···N2 intermolecular hydrogen bonds, generating rings of R²₂(10) graph-set motif (Fig. 2).

Related literature top

For the structures of related hexahydropyrimidines, see: Al-Resayes (2009); Song et al. (2010); Jayaratna & Norman (2010); Fun & Kia (2008). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A solution of 2-dipyridlketone (0.5 g, 2.9 mmol) in anhydrous ethanol (15 mL) was mixed with 2,2-dimethyl-1,3-propanediamine (0.22 mL, 3.0 mmoL) and allowed to reflux for about six hours. The resulting mixture was concentrated under reduced pressure and the title compound was precipitated by the addition of 50 mL of ice cool distilled water. The precipitates were filtered off, washed three times with 20 mL of distilled water, recrystallized in ethanol and allowed to stand at room temperature. After three days, colourless crystals suitable for single-crystal X-ray data collection were obtained (0.63 g, yield 87%). All chemicals were purchased from Acros.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level. Dashed line indicates the intramolecular hydrogen bond. Hydrogen atoms not involved in hydrogen bonds are omitted for clarity.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. Only hydrogen atoms involved in hydrogen bonding (dashed lines) are shown.

5,5-Dimethyl-2,2-bis(pyridin-2-yl)-1,3-diazinane top

Crystal data top

C₁₆H₂₀N₄	Z = 2
M_r = 268.36	F(000) = 288
Triclinic, P1	D_x = 1.191 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5535 (7) Å	Cell parameters from 3809 reflections
b = 8.7124 (8) Å	θ = 2.6–28.3°
c = 11.7241 (10) Å	µ = 0.07 mm⁻¹
α = 109.824 (2)°	T = 298 K
β = 96.444 (2)°	Block, colourless
γ = 109.658 (2)°	0.48 × 0.42 × 0.39 mm
V = 748.33 (11) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2794 independent reflections
Radiation source: fine-focus sealed tube	2422 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scan	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
T_min = 0.966, T_max = 0.972	k = −10→10
8514 measured reflections	l = −14→14

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0507P)² + 0.1284P] where P = (F_o² + 2F_c²)/3
2794 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₆H₂₀N₄	γ = 109.658 (2)°
M_r = 268.36	V = 748.33 (11) Å³
Triclinic, P1	Z = 2
a = 8.5535 (7) Å	Mo Kα radiation
b = 8.7124 (8) Å	µ = 0.07 mm⁻¹
c = 11.7241 (10) Å	T = 298 K
α = 109.824 (2)°	0.48 × 0.42 × 0.39 mm
β = 96.444 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2794 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2422 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.972	R_int = 0.016
8514 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.15 e Å⁻³
2794 reflections	Δρ_min = −0.17 e Å⁻³
191 parameters

Special details top

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
N1	0.77584 (15)	0.69943 (16)	0.23880 (11)	0.0588 (3)
N2	0.52797 (14)	0.27820 (13)	0.38100 (9)	0.0441 (3)
N3	0.48652 (13)	0.40322 (14)	0.11970 (9)	0.0414 (3)
N4	0.45050 (13)	0.53799 (13)	0.32684 (9)	0.0408 (3)
C1	0.9335 (2)	0.8284 (2)	0.28056 (17)	0.0732 (5)
H1B	0.9634	0.9024	0.2381	0.088*
C2	1.0538 (2)	0.8587 (2)	0.38177 (17)	0.0741 (5)
H2B	1.1621	0.9506	0.4075	0.089*
C3	1.0101 (2)	0.7500 (2)	0.44384 (18)	0.0772 (5)
H3B	1.0884	0.7667	0.5133	0.093*
C4	0.84908 (19)	0.6155 (2)	0.40254 (14)	0.0635 (4)
H4B	0.8173	0.5398	0.4436	0.076*
C5	0.73434 (16)	0.59355 (16)	0.29919 (11)	0.0418 (3)
C6	0.54948 (15)	0.45228 (15)	0.25295 (10)	0.0371 (3)
C7	0.54779 (14)	0.28446 (15)	0.27106 (10)	0.0371 (3)
C8	0.57432 (17)	0.15174 (17)	0.17968 (12)	0.0464 (3)
H8A	0.5886	0.1597	0.1041	0.056*
C9	0.57920 (19)	0.00820 (18)	0.20247 (13)	0.0557 (4)
H9A	0.5958	−0.0825	0.1421	0.067*
C10	0.55928 (18)	0.00035 (17)	0.31533 (13)	0.0529 (3)
H10A	0.5625	−0.0949	0.3332	0.063*
C11	0.53455 (18)	0.13749 (17)	0.40084 (12)	0.0495 (3)
H11A	0.5215	0.1325	0.4774	0.059*
C12	0.30105 (16)	0.30123 (17)	0.07347 (11)	0.0452 (3)
H12A	0.2747	0.1844	0.0745	0.054*
H12B	0.2666	0.2844	−0.0131	0.054*
C13	0.19391 (16)	0.38596 (18)	0.14765 (12)	0.0482 (3)
C14	0.26589 (16)	0.42847 (18)	0.28538 (12)	0.0481 (3)
H14A	0.2074	0.4911	0.3369	0.058*
H14B	0.2444	0.3183	0.2962	0.058*
C15	0.0071 (2)	0.2539 (2)	0.10458 (17)	0.0744 (5)
H15A	0.0000	0.1476	0.1154	0.112*
H15B	−0.0376	0.2248	0.0176	0.112*
H15C	−0.0588	0.3060	0.1535	0.112*
C16	0.2069 (2)	0.5537 (2)	0.12841 (15)	0.0634 (4)
H16A	0.1669	0.5240	0.0407	0.095*
H16B	0.3243	0.6381	0.1585	0.095*
H16C	0.1376	0.6048	0.1739	0.095*
H4A	0.4891 (17)	0.5588 (17)	0.4059 (14)	0.049 (4)*
H3A	0.5166 (18)	0.502 (2)	0.1080 (13)	0.051 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0570 (7)	0.0547 (7)	0.0576 (7)	0.0107 (6)	0.0113 (6)	0.0271 (6)
N2	0.0578 (6)	0.0430 (6)	0.0357 (5)	0.0239 (5)	0.0133 (5)	0.0164 (4)
N3	0.0465 (6)	0.0455 (6)	0.0314 (5)	0.0176 (5)	0.0093 (4)	0.0156 (4)
N4	0.0509 (6)	0.0441 (6)	0.0308 (5)	0.0250 (5)	0.0112 (4)	0.0130 (4)
C1	0.0675 (10)	0.0612 (9)	0.0758 (11)	0.0059 (8)	0.0196 (9)	0.0294 (8)
C2	0.0477 (8)	0.0607 (10)	0.0834 (12)	0.0063 (7)	0.0121 (8)	0.0102 (9)
C3	0.0560 (10)	0.0700 (10)	0.0780 (11)	0.0142 (8)	−0.0112 (8)	0.0177 (9)
C4	0.0582 (9)	0.0594 (9)	0.0599 (9)	0.0138 (7)	−0.0033 (7)	0.0246 (7)
C5	0.0463 (7)	0.0389 (6)	0.0384 (6)	0.0190 (5)	0.0105 (5)	0.0115 (5)
C6	0.0440 (6)	0.0386 (6)	0.0294 (6)	0.0187 (5)	0.0099 (5)	0.0120 (5)
C7	0.0383 (6)	0.0380 (6)	0.0328 (6)	0.0158 (5)	0.0078 (5)	0.0116 (5)
C8	0.0555 (8)	0.0464 (7)	0.0395 (6)	0.0249 (6)	0.0171 (6)	0.0140 (5)
C9	0.0697 (9)	0.0459 (7)	0.0539 (8)	0.0322 (7)	0.0197 (7)	0.0126 (6)
C10	0.0636 (9)	0.0413 (7)	0.0568 (8)	0.0246 (6)	0.0116 (6)	0.0208 (6)
C11	0.0623 (8)	0.0482 (7)	0.0434 (7)	0.0245 (6)	0.0138 (6)	0.0223 (6)
C12	0.0490 (7)	0.0460 (7)	0.0341 (6)	0.0176 (6)	0.0044 (5)	0.0123 (5)
C13	0.0436 (7)	0.0511 (7)	0.0481 (7)	0.0204 (6)	0.0081 (6)	0.0175 (6)
C14	0.0508 (7)	0.0547 (8)	0.0476 (7)	0.0277 (6)	0.0208 (6)	0.0216 (6)
C15	0.0485 (9)	0.0805 (11)	0.0793 (11)	0.0187 (8)	0.0106 (8)	0.0238 (9)
C16	0.0696 (10)	0.0649 (9)	0.0607 (9)	0.0374 (8)	0.0055 (7)	0.0241 (7)

Geometric parameters (Å, º) top

N1—C5	1.3256 (17)	C8—C9	1.3771 (18)
N1—C1	1.3339 (19)	C8—H8A	0.9300
N2—C7	1.3354 (15)	C9—C10	1.374 (2)
N2—C11	1.3406 (16)	C9—H9A	0.9300
N3—C6	1.4549 (14)	C10—C11	1.3721 (19)
N3—C12	1.4601 (16)	C10—H10A	0.9300
N3—H3A	0.878 (15)	C11—H11A	0.9300
N4—C14	1.4627 (16)	C12—C13	1.5296 (18)
N4—C6	1.4751 (14)	C12—H12A	0.9700
N4—H4A	0.883 (15)	C12—H12B	0.9700
C1—C2	1.367 (3)	C13—C15	1.5230 (19)
C1—H1B	0.9300	C13—C16	1.5231 (19)
C2—C3	1.362 (3)	C13—C14	1.5301 (18)
C2—H2B	0.9300	C14—H14A	0.9700
C3—C4	1.373 (2)	C14—H14B	0.9700
C3—H3B	0.9300	C15—H15A	0.9600
C4—C5	1.3847 (19)	C15—H15B	0.9600
C4—H4B	0.9300	C15—H15C	0.9600
C5—C6	1.5345 (16)	C16—H16A	0.9600
C6—C7	1.5428 (16)	C16—H16B	0.9600
C7—C8	1.3883 (16)	C16—H16C	0.9600

C5—N1—C1	117.63 (13)	C8—C9—H9A	120.3
C7—N2—C11	117.43 (11)	C11—C10—C9	117.89 (12)
C6—N3—C12	113.05 (9)	C11—C10—H10A	121.1
C6—N3—H3A	107.0 (9)	C9—C10—H10A	121.1
C12—N3—H3A	110.8 (9)	N2—C11—C10	124.11 (12)
C14—N4—C6	112.88 (9)	N2—C11—H11A	117.9
C14—N4—H4A	109.5 (9)	C10—C11—H11A	117.9
C6—N4—H4A	107.7 (9)	N3—C12—C13	114.99 (10)
N1—C1—C2	124.19 (16)	N3—C12—H12A	108.5
N1—C1—H1B	117.9	C13—C12—H12A	108.5
C2—C1—H1B	117.9	N3—C12—H12B	108.5
C3—C2—C1	117.92 (15)	C13—C12—H12B	108.5
C3—C2—H2B	121.0	H12A—C12—H12B	107.5
C1—C2—H2B	121.0	C15—C13—C16	109.87 (12)
C2—C3—C4	119.16 (16)	C15—C13—C12	109.76 (11)
C2—C3—H3B	120.4	C16—C13—C12	109.97 (11)
C4—C3—H3B	120.4	C15—C13—C14	109.29 (12)
C3—C4—C5	119.43 (15)	C16—C13—C14	111.33 (11)
C3—C4—H4B	120.3	C12—C13—C14	106.57 (10)
C5—C4—H4B	120.3	N4—C14—C13	111.30 (10)
N1—C5—C4	121.67 (13)	N4—C14—H14A	109.4
N1—C5—C6	116.42 (11)	C13—C14—H14A	109.4
C4—C5—C6	121.82 (12)	N4—C14—H14B	109.4
N3—C6—N4	111.25 (9)	C13—C14—H14B	109.4
N3—C6—C5	109.18 (9)	H14A—C14—H14B	108.0
N4—C6—C5	105.31 (9)	C13—C15—H15A	109.5
N3—C6—C7	108.16 (9)	C13—C15—H15B	109.5
N4—C6—C7	113.60 (9)	H15A—C15—H15B	109.5
C5—C6—C7	109.24 (9)	C13—C15—H15C	109.5
N2—C7—C8	122.12 (11)	H15A—C15—H15C	109.5
N2—C7—C6	116.56 (10)	H15B—C15—H15C	109.5
C8—C7—C6	121.24 (10)	C13—C16—H16A	109.5
C9—C8—C7	119.09 (12)	C13—C16—H16B	109.5
C9—C8—H8A	120.5	H16A—C16—H16B	109.5
C7—C8—H8A	120.5	C13—C16—H16C	109.5
C10—C9—C8	119.35 (12)	H16A—C16—H16C	109.5
C10—C9—H9A	120.3	H16B—C16—H16C	109.5

C5—N1—C1—C2	−0.5 (3)	C11—N2—C7—C6	−176.83 (10)
N1—C1—C2—C3	0.1 (3)	N3—C6—C7—N2	−151.87 (10)
C1—C2—C3—C4	0.2 (3)	N4—C6—C7—N2	−27.85 (14)
C2—C3—C4—C5	−0.3 (3)	C5—C6—C7—N2	89.39 (12)
C1—N1—C5—C4	0.4 (2)	N3—C6—C7—C8	31.27 (15)
C1—N1—C5—C6	177.15 (12)	N4—C6—C7—C8	155.30 (11)
C3—C4—C5—N1	−0.1 (2)	C5—C6—C7—C8	−87.47 (13)
C3—C4—C5—C6	−176.63 (13)	N2—C7—C8—C9	0.47 (19)
C12—N3—C6—N4	−51.01 (13)	C6—C7—C8—C9	177.15 (11)
C12—N3—C6—C5	−166.81 (9)	C7—C8—C9—C10	−0.6 (2)
C12—N3—C6—C7	74.41 (12)	C8—C9—C10—C11	0.2 (2)
C14—N4—C6—N3	55.48 (13)	C7—N2—C11—C10	−0.4 (2)
C14—N4—C6—C5	173.65 (9)	C9—C10—C11—N2	0.3 (2)
C14—N4—C6—C7	−66.85 (12)	C6—N3—C12—C13	52.20 (14)
N1—C5—C6—N3	29.03 (14)	N3—C12—C13—C15	−170.46 (11)
C4—C5—C6—N3	−154.24 (12)	N3—C12—C13—C16	68.56 (14)
N1—C5—C6—N4	−90.52 (12)	N3—C12—C13—C14	−52.23 (14)
C4—C5—C6—N4	86.21 (14)	C6—N4—C14—C13	−58.94 (13)
N1—C5—C6—C7	147.13 (11)	C15—C13—C14—N4	173.16 (11)
C4—C5—C6—C7	−36.15 (15)	C16—C13—C14—N4	−65.29 (14)
C11—N2—C7—C8	0.00 (18)	C12—C13—C14—N4	54.62 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N2ⁱ	0.882 (15)	2.469 (15)	3.2048 (14)	141.3 (13)
C4—H4B···N2	0.93	2.55	3.187 (2)	126

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀N₄
M_r	268.36
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.5535 (7), 8.7124 (8), 11.7241 (10)
α, β, γ (°)	109.824 (2), 96.444 (2), 109.658 (2)
V (Å³)	748.33 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.48 × 0.42 × 0.39

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.966, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	8514, 2794, 2422
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.05
No. of reflections	2794
No. of parameters	191
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N2ⁱ	0.882 (15)	2.469 (15)	3.2048 (14)	141.3 (13)
C4—H4B···N2	0.9300	2.5500	3.187 (2)	126.00

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

IW, AA, SIA-R and MIC are thankful for the finanicial support of the King Saud University, Deanship of Scientific Research, College of Science Research Center for the research project.

References

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