N2,N2,N4,N4,N6,N6-Hexapropyl-1,3,5-triazine-2,4,6-triamine

Li, Y.-F.; Jian, F.-F.

doi:10.1107/S1600536808025166

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1744

doi:10.1107/S1600536808025166

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N²,N²,N⁴,N⁴,N⁶,N⁶-Hexapropyl-1,3,5-triazine-2,4,6-triamine

Yu-Feng Li ^a and Fang-Fang Jian ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 30 July 2008; accepted 5 August 2008; online 13 August 2008)

The title compound, C₂₁H₄₂N₆, was prepared by the reaction of 2,4,6-trichloro-1,3,5-triazine with dipropylamine. The structure of the molecule is tripodal.

Related literature

For related literature, see: Frassanito et al. (1996 ); Bishop et al. (2002 ).

Experimental

Crystal data

C₂₁H₄₂N₆
M_r = 378.61
Triclinic, $[P \overline 1]$
a = 9.847 (2) Å
b = 12.044 (2) Å
c = 12.910 (3) Å
α = 116.57 (2)°
β = 96.94 (4)°
γ = 106.81 (3)°
V = 1253.7 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 295 (2) K
0.32 × 0.24 × 0.13 mm

Data collection

Bruker P4 diffractometer
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997 ) T_min = 0.981, T_max = 0.992
5686 measured reflections
5364 independent reflections
1966 reflections with I > 2σ(I)
R_int = 0.019
3 standard reflections
every 100 reflections
intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.179
S = 1.00
5364 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: XSCANS (Bruker, 1996 ); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025166/at2607sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025166/at2607Isup2.hkl

checkCIF report

Comment top

Triazine have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Frassanito et al., 1996). As part of our search for new triazine compounds, we synthesized the title compound (I), and describe its structure here.

In the title compound (I) (Fig. 1), the non-hydrogen atoms of the triazine ring are almost in the same plane, with a maximum deviation of 0.016 (3) Å for C19. The C20—N2 bond length of 1.361 (3)Å is comparable with C—N bond [1.334 (2) Å] reported (Bishop et al., 2002). In the structure, there is no classical hydrogen bonds.

Related literature top

For related literature, see: Frassanito et al. (1996); Bishop et al. (2002).

Experimental top

A mixture of the 2,4,6-trichloro-1,3,5-triazine (0.1 mol), and dipropylamine (0.4 mol) was stirred in refluxing ethanol (30 mL) for 5 h to afford the title compound (0.084 mol, yield 84%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS (Bruker, 1996); data reduction: SHELXTL (Sheldrick, 2008); 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).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

N²,N²,N⁴,N⁴,N⁶,N⁶-Hexapropyl-1,3,5-triazine-2,4,6-triamine top

Crystal data top

C₂₁H₄₂N₆	Z = 2
M_r = 378.61	F(000) = 420
Triclinic, P1	D_x = 1.003 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.847 (2) Å	Cell parameters from 5779 reflections
b = 12.044 (2) Å	θ = 1.9–26.8°
c = 12.910 (3) Å	µ = 0.06 mm⁻¹
α = 116.57 (2)°	T = 295 K
β = 96.94 (4)°	Prism, colourless
γ = 106.81 (3)°	0.32 × 0.24 × 0.13 mm
V = 1253.7 (7) Å³

Data collection top

Bruker P4 diffractometer	1966 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 27.0°, θ_min = 1.8°
ω scans	h = 0→11
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	k = −14→14
T_min = 0.981, T_max = 0.992	l = −15→15
5686 measured reflections	3 standard reflections every 100 reflections
5364 independent reflections	intensity decay: none

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)] = 0.067	H-atom parameters constrained
wR(F²) = 0.179	1/[σ²(F_o²) + 0.5P + (0.04P)² + sinθ/λ], where P = 0.5F_o² + 0.5F_c²
S = 1.00	(Δ/σ)_max < 0.001
5364 reflections	Δρ_max = 0.32 e Å⁻³
245 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.061 (3)

Crystal data top

C₂₁H₄₂N₆	γ = 106.81 (3)°
M_r = 378.61	V = 1253.7 (7) Å³
Triclinic, P1	Z = 2
a = 9.847 (2) Å	Mo Kα radiation
b = 12.044 (2) Å	µ = 0.06 mm⁻¹
c = 12.910 (3) Å	T = 295 K
α = 116.57 (2)°	0.32 × 0.24 × 0.13 mm
β = 96.94 (4)°

Data collection top

Bruker P4 diffractometer	1966 reflections with I > 2σ(I)
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	R_int = 0.019
T_min = 0.981, T_max = 0.992	3 standard reflections every 100 reflections
5686 measured reflections	intensity decay: none
5364 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.00	Δρ_max = 0.32 e Å⁻³
5364 reflections	Δρ_min = −0.17 e Å⁻³
245 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	0.4912 (3)	0.6819 (2)	0.6032 (2)	0.0771 (7)
N2	0.0405 (3)	0.3446 (2)	0.5011 (2)	0.0786 (7)
N3	0.1842 (3)	0.4375 (3)	0.2129 (2)	0.0921 (8)
N4	0.3388 (3)	0.5651 (2)	0.4067 (2)	0.0706 (7)
N5	0.2667 (3)	0.5137 (2)	0.55636 (19)	0.0705 (6)
N6	0.1080 (3)	0.3826 (2)	0.3515 (2)	0.0713 (7)
C1	0.5019 (5)	0.8038 (5)	0.9325 (3)	0.1492 (17)
H1A	0.4615	0.8624	0.9856	0.224*
H1B	0.6076	0.8398	0.9664	0.224*
H1C	0.4595	0.7162	0.9231	0.224*
C2	0.4656 (4)	0.7929 (4)	0.8097 (3)	0.1069 (11)
H2A	0.3589	0.7575	0.7757	0.128*
H2B	0.5069	0.8817	0.8192	0.128*
C3	0.5281 (3)	0.7023 (3)	0.7252 (3)	0.0900 (10)
H3A	0.6352	0.7404	0.7584	0.108*
H3B	0.4909	0.6156	0.7201	0.108*
C4	0.6951 (4)	0.9729 (4)	0.5583 (4)	0.1302 (14)
H4A	0.6774	1.0520	0.5724	0.195*
H4B	0.6883	0.9206	0.4745	0.195*
H4C	0.7923	0.9987	0.6075	0.195*
C5	0.5798 (4)	0.8894 (3)	0.5909 (3)	0.1069 (11)
H5A	0.5856	0.9435	0.6752	0.128*
H5B	0.4817	0.8650	0.5420	0.128*
C6	0.6005 (3)	0.7640 (3)	0.5718 (3)	0.0853 (9)
H6A	0.5946	0.7102	0.4874	0.102*
H6B	0.6990	0.7888	0.6202	0.102*
C7	0.1670 (5)	0.3639 (5)	0.8037 (3)	0.1554 (18)
H7A	0.2222	0.3208	0.8272	0.233*
H7B	0.0717	0.3407	0.8172	0.233*
H7C	0.2201	0.4598	0.8510	0.233*
C8	0.1462 (5)	0.3165 (4)	0.6678 (3)	0.1200 (13)
H8A	0.2426	0.3380	0.6538	0.144*
H8B	0.0932	0.2196	0.6200	0.144*
C9	0.0622 (4)	0.3824 (3)	0.6288 (3)	0.0927 (10)
H9A	−0.0341	0.3594	0.6426	0.111*
H9B	0.1146	0.4792	0.6790	0.111*
C10	−0.2179 (5)	−0.0011 (4)	0.2490 (4)	0.1599 (18)
H10A	−0.2036	−0.0841	0.2094	0.240*
H10B	−0.2402	0.0254	0.1912	0.240*
H10C	−0.2987	−0.0133	0.2830	0.240*
C11	−0.0829 (4)	0.1031 (4)	0.3453 (3)	0.1207 (13)
H11A	−0.0013	0.1139	0.3107	0.145*
H11B	−0.0596	0.0749	0.4024	0.145*
C12	−0.0979 (3)	0.2375 (3)	0.4121 (3)	0.0880 (9)
H12A	−0.1298	0.2618	0.3539	0.106*
H12B	−0.1737	0.2286	0.4526	0.106*
C13	−0.1129 (5)	0.1115 (4)	−0.0532 (4)	0.1646 (19)
H13A	−0.1114	0.0240	−0.1008	0.247*
H13B	−0.1299	0.1473	−0.1045	0.247*
H13C	−0.1910	0.1045	−0.0157	0.247*
C14	0.0419 (5)	0.2090 (4)	0.0485 (4)	0.1355 (15)
H14A	0.0606	0.1727	0.0999	0.163*
H14B	0.1213	0.2167	0.0113	0.163*
C15	0.0374 (4)	0.3384 (4)	0.1194 (3)	0.1107 (12)
H15A	−0.0391	0.3305	0.1594	0.133*
H15B	0.0122	0.3714	0.0666	0.133*
C16	0.4074 (6)	0.7152 (5)	0.1645 (5)	0.194 (2)
H16A	0.3964	0.7963	0.1762	0.291*
H16B	0.4037	0.6610	0.0818	0.291*
H16C	0.5010	0.7376	0.2169	0.291*
C17	0.2822 (5)	0.6369 (4)	0.1941 (4)	0.1364 (15)
H17A	0.2853	0.6916	0.2775	0.164*
H17B	0.1875	0.6155	0.1423	0.164*
C18	0.2973 (4)	0.5110 (3)	0.1757 (3)	0.1099 (12)
H18A	0.2867	0.4537	0.0909	0.132*
H18B	0.3955	0.5324	0.2224	0.132*
C19	0.3614 (3)	0.5835 (3)	0.5187 (3)	0.0672 (7)
C20	0.1420 (3)	0.4161 (3)	0.4683 (3)	0.0672 (7)
C21	0.2109 (4)	0.4625 (3)	0.3276 (2)	0.0689 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0721 (17)	0.0766 (16)	0.0648 (16)	0.0163 (14)	0.0150 (14)	0.0306 (13)
N2	0.0749 (17)	0.0800 (17)	0.0733 (16)	0.0149 (14)	0.0245 (14)	0.0413 (14)
N3	0.096 (2)	0.0876 (18)	0.0616 (16)	0.0011 (16)	0.0113 (15)	0.0375 (14)
N4	0.0734 (17)	0.0688 (15)	0.0576 (14)	0.0195 (14)	0.0176 (13)	0.0279 (12)
N5	0.0706 (16)	0.0686 (15)	0.0648 (15)	0.0181 (13)	0.0186 (14)	0.0336 (13)
N6	0.0726 (17)	0.0701 (15)	0.0659 (16)	0.0193 (13)	0.0201 (12)	0.0353 (13)
C1	0.172 (4)	0.183 (4)	0.082 (3)	0.065 (4)	0.041 (3)	0.060 (3)
C2	0.108 (3)	0.110 (3)	0.089 (2)	0.042 (2)	0.026 (2)	0.041 (2)
C3	0.074 (2)	0.089 (2)	0.082 (2)	0.0237 (18)	0.0119 (17)	0.0308 (18)
C4	0.128 (3)	0.117 (3)	0.176 (4)	0.043 (3)	0.064 (3)	0.096 (3)
C5	0.110 (3)	0.100 (3)	0.127 (3)	0.045 (2)	0.047 (2)	0.065 (2)
C6	0.064 (2)	0.085 (2)	0.092 (2)	0.0170 (17)	0.0177 (17)	0.0406 (18)
C7	0.208 (5)	0.207 (5)	0.107 (3)	0.106 (4)	0.065 (3)	0.104 (3)
C8	0.142 (4)	0.133 (3)	0.119 (3)	0.072 (3)	0.055 (3)	0.075 (3)
C9	0.090 (2)	0.103 (2)	0.107 (3)	0.039 (2)	0.046 (2)	0.066 (2)
C10	0.134 (4)	0.112 (3)	0.163 (4)	0.019 (3)	0.011 (3)	0.039 (3)
C11	0.099 (3)	0.094 (3)	0.127 (3)	0.010 (2)	0.003 (2)	0.046 (2)
C12	0.074 (2)	0.084 (2)	0.098 (2)	0.0205 (18)	0.0306 (19)	0.045 (2)
C13	0.134 (4)	0.126 (3)	0.122 (3)	0.009 (3)	−0.016 (3)	0.013 (3)
C14	0.142 (4)	0.134 (4)	0.134 (3)	0.065 (3)	0.048 (3)	0.061 (3)
C15	0.143 (4)	0.098 (3)	0.091 (3)	0.041 (3)	0.043 (3)	0.049 (2)
C16	0.199 (5)	0.192 (5)	0.210 (5)	0.022 (4)	0.079 (5)	0.145 (5)
C17	0.135 (4)	0.155 (4)	0.142 (4)	0.049 (3)	0.046 (3)	0.096 (3)
C18	0.144 (3)	0.092 (3)	0.075 (2)	0.026 (2)	0.019 (2)	0.043 (2)
C19	0.071 (2)	0.0604 (17)	0.0604 (18)	0.0230 (16)	0.0166 (16)	0.0252 (15)
C20	0.072 (2)	0.0647 (18)	0.069 (2)	0.0267 (16)	0.0256 (17)	0.0355 (16)
C21	0.080 (2)	0.0698 (18)	0.0536 (17)	0.0290 (17)	0.0182 (16)	0.0295 (15)

Geometric parameters (Å, º) top

N1—C19	1.363 (3)	C7—H7B	0.9600
N1—C3	1.462 (3)	C7—H7C	0.9600
N1—C6	1.466 (3)	C8—C9	1.485 (4)
N2—C20	1.361 (3)	C8—H8A	0.9700
N2—C12	1.456 (4)	C8—H8B	0.9700
N2—C9	1.469 (4)	C9—H9A	0.9700
N3—C21	1.346 (3)	C9—H9B	0.9700
N3—C18	1.481 (4)	C10—C11	1.458 (5)
N3—C15	1.505 (4)	C10—H10A	0.9600
N4—C19	1.339 (3)	C10—H10B	0.9600
N4—C21	1.348 (3)	C10—H10C	0.9600
N5—C20	1.347 (3)	C11—C12	1.518 (4)
N5—C19	1.355 (3)	C11—H11A	0.9700
N6—C21	1.350 (3)	C11—H11B	0.9700
N6—C20	1.343 (3)	C12—H12A	0.9700
C1—C2	1.520 (4)	C12—H12B	0.9700
C1—H1A	0.9600	C13—C14	1.590 (5)
C1—H1B	0.9600	C13—H13A	0.9600
C1—H1C	0.9600	C13—H13B	0.9600
C2—C3	1.499 (4)	C13—H13C	0.9600
C2—H2A	0.9700	C14—C15	1.429 (5)
C2—H2B	0.9700	C14—H14A	0.9700
C3—H3A	0.9700	C14—H14B	0.9700
C3—H3B	0.9700	C15—H15A	0.9700
C4—C5	1.520 (4)	C15—H15B	0.9700
C4—H4A	0.9600	C16—C17	1.522 (5)
C4—H4B	0.9600	C16—H16A	0.9600
C4—H4C	0.9600	C16—H16B	0.9600
C5—C6	1.496 (4)	C16—H16C	0.9600
C5—H5A	0.9700	C17—C18	1.482 (5)
C5—H5B	0.9700	C17—H17A	0.9700
C6—H6A	0.9700	C17—H17B	0.9700
C6—H6B	0.9700	C18—H18A	0.9700
C7—C8	1.548 (4)	C18—H18B	0.9700
C7—H7A	0.9600

C19—N1—C3	120.5 (3)	H9A—C9—H9B	107.6
C19—N1—C6	120.8 (2)	C11—C10—H10A	109.5
C3—N1—C6	118.5 (2)	C11—C10—H10B	109.5
C20—N2—C12	120.5 (2)	H10A—C10—H10B	109.5
C20—N2—C9	120.5 (3)	C11—C10—H10C	109.5
C12—N2—C9	118.8 (2)	H10A—C10—H10C	109.5
C21—N3—C18	120.8 (3)	H10B—C10—H10C	109.5
C21—N3—C15	121.6 (3)	C10—C11—C12	112.3 (3)
C18—N3—C15	117.5 (3)	C10—C11—H11A	109.2
C19—N4—C21	113.6 (2)	C12—C11—H11A	109.2
C20—N5—C19	113.8 (2)	C10—C11—H11B	109.2
C21—N6—C20	113.2 (2)	C12—C11—H11B	109.2
C2—C1—H1A	109.5	H11A—C11—H11B	107.9
C2—C1—H1B	109.5	N2—C12—C11	112.4 (3)
H1A—C1—H1B	109.5	N2—C12—H12A	109.1
C2—C1—H1C	109.5	C11—C12—H12A	109.1
H1A—C1—H1C	109.5	N2—C12—H12B	109.1
H1B—C1—H1C	109.5	C11—C12—H12B	109.1
C3—C2—C1	110.5 (3)	H12A—C12—H12B	107.8
C3—C2—H2A	109.6	C14—C13—H13A	109.5
C1—C2—H2A	109.6	C14—C13—H13B	109.5
C3—C2—H2B	109.6	H13A—C13—H13B	109.5
C1—C2—H2B	109.6	C14—C13—H13C	109.5
H2A—C2—H2B	108.1	H13A—C13—H13C	109.5
N1—C3—C2	113.4 (3)	H13B—C13—H13C	109.5
N1—C3—H3A	108.9	C15—C14—C13	108.8 (4)
C2—C3—H3A	108.9	C15—C14—H14A	109.9
N1—C3—H3B	108.9	C13—C14—H14A	109.9
C2—C3—H3B	108.9	C15—C14—H14B	109.9
H3A—C3—H3B	107.7	C13—C14—H14B	109.9
C5—C4—H4A	109.5	H14A—C14—H14B	108.3
C5—C4—H4B	109.5	C14—C15—N3	111.3 (3)
H4A—C4—H4B	109.5	C14—C15—H15A	109.4
C5—C4—H4C	109.5	N3—C15—H15A	109.4
H4A—C4—H4C	109.5	C14—C15—H15B	109.4
H4B—C4—H4C	109.5	N3—C15—H15B	109.4
C6—C5—C4	112.6 (3)	H15A—C15—H15B	108.0
C6—C5—H5A	109.1	C17—C16—H16A	109.5
C4—C5—H5A	109.1	C17—C16—H16B	109.5
C6—C5—H5B	109.1	H16A—C16—H16B	109.5
C4—C5—H5B	109.1	C17—C16—H16C	109.5
H5A—C5—H5B	107.8	H16A—C16—H16C	109.5
N1—C6—C5	113.8 (3)	H16B—C16—H16C	109.5
N1—C6—H6A	108.8	C18—C17—C16	110.0 (4)
C5—C6—H6A	108.8	C18—C17—H17A	109.7
N1—C6—H6B	108.8	C16—C17—H17A	109.7
C5—C6—H6B	108.8	C18—C17—H17B	109.7
H6A—C6—H6B	107.7	C16—C17—H17B	109.7
C8—C7—H7A	109.5	H17A—C17—H17B	108.2
C8—C7—H7B	109.5	N3—C18—C17	111.5 (3)
H7A—C7—H7B	109.5	N3—C18—H18A	109.3
C8—C7—H7C	109.5	C17—C18—H18A	109.3
H7A—C7—H7C	109.5	N3—C18—H18B	109.3
H7B—C7—H7C	109.5	C17—C18—H18B	109.3
C9—C8—C7	110.8 (3)	H18A—C18—H18B	108.0
C9—C8—H8A	109.5	N4—C19—N5	126.1 (3)
C7—C8—H8A	109.5	N4—C19—N1	117.3 (3)
C9—C8—H8B	109.5	N5—C19—N1	116.6 (3)
C7—C8—H8B	109.5	N5—C20—N6	126.5 (3)
H8A—C8—H8B	108.1	N5—C20—N2	116.6 (3)
N2—C9—C8	114.1 (3)	N6—C20—N2	116.9 (3)
N2—C9—H9A	108.7	N6—C21—N3	117.1 (3)
C8—C9—H9A	108.7	N6—C21—N4	126.8 (3)
N2—C9—H9B	108.7	N3—C21—N4	116.1 (3)
C8—C9—H9B	108.7

Experimental details

Crystal data
Chemical formula	C₂₁H₄₂N₆
M_r	378.61
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.847 (2), 12.044 (2), 12.910 (3)
α, β, γ (°)	116.57 (2), 96.94 (4), 106.81 (3)
V (Å³)	1253.7 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.32 × 0.24 × 0.13

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)
T_min, T_max	0.981, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	5686, 5364, 1966
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.179, 1.00
No. of reflections	5364
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.17

Computer programs: XSCANS (Bruker, 1996), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

References

Bishop, M. M., Lindoy, L. F. & Skelton, B. W. (2002). J. Chem. Soc., Dalton Trans. pp. 377–382. Google Scholar
Bruker, (1996). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Frassanito, R., De Socio, G., Laura, D. & Rotilio, D. (1996). J. Agric. Food Chem. 44, 2282–2286. CrossRef CAS Web of Science Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar