6-Chloro-N2,N4-di-p-tolyl-1,3,5-triazine-2,4-diamine dimethyl­formamide monosolvate

Jian, F.; Xiao, H.; Wei, Y.

doi:10.1107/S1600536809049885

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3212

doi:10.1107/S1600536809049885

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6-Chloro-N²,N⁴-di-p-tolyl-1,3,5-triazine-2,4-diamine dimethylformamide monosolvate

Fangfang Jian,^a ^* Hailian Xiao ^b and Yongxiang Wei ^b

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, and ^bNew Materials & Function, Coordination Chemistry Laboratory, Qingdao University of Science & Technology, Qingdao, 266042, People's Republic of China
^*Correspondence e-mail: xiaohailian@163.com

(Received 12 November 2009; accepted 20 November 2009; online 25 November 2009)

The title compound, C₁₇H₁₆ClN₅·C₃H₇NO, was prepared by reaction of p-toluidine with 2,4,6-trichloro-1,3,5-triazine at room temperature. The dihedral angles between the triazine ring and the pendant rings are 3.61 (12) and 53.11 (12)°. An intramolecular C—H⋯N interaction occurs. The packing is stabilized by N—H⋯N and N—H⋯O hydrogen bonds and C—H⋯π and π–π [centroid–centroid distance = 3.763 (1) Å] interactions.

Related literature

For the use of 1,3,5-triazine derivatives as starting materials for drugs and as light stabilisers, see: Azev et al. (2003 ); Steffensen and Simanek (2003 ). For related structures, see: Zeng et al. (2005a ,b ); Jian et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₆ClN₅·C₃H₇NO
M_r = 398.89
Triclinic, $[P \overline 1]$
a = 6.821 (2) Å
b = 10.980 (2) Å
c = 14.060 (3) Å
α = 91.13 (3)°
β = 94.29 (2)°
γ = 98.32 (4)°
V = 1038.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
5740 measured reflections
3832 independent reflections
2786 reflections with I > 2σ(I)
R_int = 0.016
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.146
S = 1.02
3832 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	2.06	2.923 (3)	177
N2—H2A⋯N5ⁱ	0.86	2.24	3.081 (3)	168
C4—H4A⋯N3	0.93	2.30	2.905 (3)	122
C1—H1D⋯Cg1ⁱⁱ	0.96	2.86	3.653 (4)	145
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x, -y+1, -z. Cg1 is the centroid of the C2–C7 ring.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97; software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049885/hg2590sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049885/hg2590Isup2.hkl

checkCIF report

Comment top

1,3,5-Triazine derivatives are of great interest due to their importance as starting materials for drugs and light stabilizers (Azev et al., 2003; Steffensen & Simanek, 2003; Zeng et al., 2005a). Our group has reported the structure of 1,3,5-triazine derivative (Jian et al., 2007). Herein, we report the synthesis and structure of the title compound.

The crystal structure consists of the host 1,3,5-triazine derivative and a guest DMF solvate molecule. The bond lengths and angles are agreement with those found in similar compounds (Zeng et al., 2005b; Jian et al., 2007). The dihedral angles formed by triazine ring and two phenyl ring are 3.61, 53.11° for C2—C7 and C9—C14, respectively. They are compared to those found in the compound that reported by our group before (Jian et al., 2007). The dihedral angle between two phenyl ring is 51.61 (2)° which is larger than that of 35.8 (1)° found in aforementioned compound.

It is interesting that there exists C—H···π and π–π interactions in the lattice [C1···Cg1=3.653 (4) Å, C1—H1D···Cg1=145.1 (1)°, Cg1···Cg2=3.763 (1) Å,Cg1 and Cg2 refer to phenyl ring C2—C7 and triazine ring, respectively]. In addition there exists N—H···O, N—H···N, C—H···N and C—H···O intra and intermolecular hydrogen bond interactions (see Table 1). All the above interactions stabilize the whole structure.

Related literature top

For the use of 1,3,5-triazine derivatives as starting materials for drugs and as light stabilizers, see: Azev et al. (2003); Steffensen and Simanek (2003). For related structures, see: Zeng et al. (2005a,b); Jian et al. (2007). Cg1 is the centroid of the C2–C7 ring.

Experimental top

The title compound was synthesized by the reaction of 2,4,6-trichloro-1,3,5-triazine (0.02 mol) and p-toluidine (0.04 mol) in acetone solvate (50 ml) under stirring for 5 h at room temperature. Single crystals suitable for x-ray measurements were obtained by recrystallization from DMF at room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

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

6-Chloro-N²,N⁴-di-p-tolyl-1,3,5-triazine-2,4-diamine dimethylformamide monosolvate top

Crystal data top

C₁₇H₁₆ClN₅·C₃H₇NO	Z = 2
M_r = 398.89	F(000) = 420
Triclinic, P1	D_x = 1.276 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.821 (2) Å	Cell parameters from 25 reflections
b = 10.980 (2) Å	θ = 4–14°
c = 14.060 (3) Å	µ = 0.21 mm⁻¹
α = 91.13 (3)°	T = 295 K
β = 94.29 (2)°	Block, colorless
γ = 98.32 (4)°	0.25 × 0.20 × 0.18 mm
V = 1038.4 (4) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.016
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 1.9°
Graphite monochromator	h = −8→8
ω scans	k = −9→13
5740 measured reflections	l = −17→16
3832 independent reflections	3 standard reflections every 100 reflections
2786 reflections with I > 2σ(I)	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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0677P)² + 0.4334P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3832 reflections	Δρ_max = 0.44 e Å⁻³
254 parameters	Δρ_min = −0.24 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: 0.008 (2)

Crystal data top

C₁₇H₁₆ClN₅·C₃H₇NO	γ = 98.32 (4)°
M_r = 398.89	V = 1038.4 (4) Å³
Triclinic, P1	Z = 2
a = 6.821 (2) Å	Mo Kα radiation
b = 10.980 (2) Å	µ = 0.21 mm⁻¹
c = 14.060 (3) Å	T = 295 K
α = 91.13 (3)°	0.25 × 0.20 × 0.18 mm
β = 94.29 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.016
5740 measured reflections	3 standard reflections every 100 reflections
3832 independent reflections	intensity decay: none
2786 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.02	Δρ_max = 0.44 e Å⁻³
3832 reflections	Δρ_min = −0.24 e Å⁻³
254 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
Cl1	1.01901 (10)	0.18643 (6)	0.38436 (5)	0.0657 (3)
N1	0.4183 (3)	0.28803 (18)	0.21951 (15)	0.0525 (5)
H1A	0.4189	0.2155	0.1954	0.063*
N2	0.7855 (3)	0.58018 (17)	0.42644 (15)	0.0493 (5)
H2A	0.8873	0.5960	0.4671	0.059*
N3	0.5954 (3)	0.44126 (17)	0.32082 (13)	0.0455 (5)
N4	0.7002 (3)	0.24467 (17)	0.29872 (14)	0.0499 (5)
N5	0.8869 (3)	0.39225 (17)	0.40810 (14)	0.0448 (5)
C1	−0.2699 (4)	0.4869 (3)	0.0743 (2)	0.0787 (9)
H1B	−0.2699	0.5683	0.1006	0.118*
H1C	−0.3862	0.4341	0.0910	0.118*
H1D	−0.2703	0.4900	0.0061	0.118*
C2	−0.0867 (4)	0.4374 (3)	0.11384 (19)	0.0598 (7)
C3	0.0514 (4)	0.5047 (3)	0.1770 (2)	0.0669 (8)
H3A	0.0313	0.5832	0.1962	0.080*
C4	0.2206 (4)	0.4597 (2)	0.2135 (2)	0.0634 (7)
H4A	0.3114	0.5081	0.2563	0.076*
C5	0.2546 (3)	0.3441 (2)	0.18675 (17)	0.0481 (6)
C6	0.1171 (4)	0.2758 (3)	0.1229 (2)	0.0639 (7)
H6A	0.1373	0.1975	0.1034	0.077*
C7	−0.0501 (4)	0.3218 (3)	0.0875 (2)	0.0706 (8)
H7A	−0.1409	0.2735	0.0446	0.085*
C8	0.3217 (5)	0.9718 (3)	0.3723 (2)	0.0756 (9)
H8A	0.4072	1.0452	0.3573	0.113*
H8B	0.2618	0.9857	0.4304	0.113*
H8C	0.2197	0.9512	0.3214	0.113*
C9	0.4419 (4)	0.8673 (2)	0.38440 (18)	0.0528 (6)
C10	0.6424 (4)	0.8851 (2)	0.3756 (2)	0.0600 (7)
H10A	0.7052	0.9628	0.3612	0.072*
C11	0.7532 (4)	0.7902 (2)	0.3877 (2)	0.0561 (7)
H11A	0.8889	0.8043	0.3804	0.067*
C12	0.6654 (3)	0.6753 (2)	0.41038 (16)	0.0437 (5)
C13	0.4652 (3)	0.6554 (2)	0.41948 (19)	0.0516 (6)
H13A	0.4028	0.5778	0.4342	0.062*
C14	0.3564 (4)	0.7512 (2)	0.4066 (2)	0.0575 (7)
H14A	0.2204	0.7367	0.4132	0.069*
C15	0.7526 (3)	0.4684 (2)	0.38338 (16)	0.0417 (5)
C16	0.5731 (3)	0.3278 (2)	0.28167 (16)	0.0454 (5)
C17	0.8473 (3)	0.2861 (2)	0.36048 (17)	0.0458 (5)
O1	0.4123 (5)	0.0448 (2)	0.1300 (2)	0.1152 (10)
N6	0.6354 (6)	−0.0890 (3)	0.1270 (2)	0.0983 (10)
C18	0.5910 (8)	0.0213 (4)	0.1365 (3)	0.1098 (14)
H18A	0.6940	0.0864	0.1484	0.132*
C19	0.8451 (8)	−0.1067 (5)	0.1350 (4)	0.1468 (19)
H19A	0.9276	−0.0283	0.1452	0.220*
H19B	0.8761	−0.1452	0.0772	0.220*
H19C	0.8689	−0.1582	0.1878	0.220*
C20	0.4959 (8)	−0.1957 (4)	0.1119 (4)	0.168 (3)
H20A	0.3643	−0.1739	0.1077	0.252*
H20B	0.5103	−0.2497	0.1640	0.252*
H20C	0.5176	−0.2367	0.0535	0.252*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0605 (4)	0.0572 (4)	0.0833 (5)	0.0336 (3)	−0.0152 (3)	−0.0046 (3)
N1	0.0481 (11)	0.0474 (11)	0.0608 (13)	0.0129 (9)	−0.0134 (10)	−0.0071 (9)
N2	0.0414 (10)	0.0435 (11)	0.0627 (13)	0.0158 (8)	−0.0145 (9)	−0.0046 (9)
N3	0.0401 (10)	0.0470 (11)	0.0500 (11)	0.0144 (8)	−0.0077 (8)	−0.0011 (9)
N4	0.0499 (11)	0.0467 (11)	0.0547 (12)	0.0185 (9)	−0.0073 (9)	−0.0018 (9)
N5	0.0382 (10)	0.0454 (11)	0.0525 (11)	0.0159 (8)	−0.0046 (8)	0.0008 (9)
C1	0.0460 (15)	0.104 (2)	0.088 (2)	0.0215 (15)	−0.0084 (14)	0.0248 (18)
C2	0.0411 (14)	0.0794 (19)	0.0597 (16)	0.0121 (13)	−0.0018 (12)	0.0200 (14)
C3	0.0584 (16)	0.0703 (18)	0.0745 (19)	0.0263 (14)	−0.0100 (14)	−0.0014 (14)
C4	0.0524 (15)	0.0630 (16)	0.0737 (18)	0.0198 (12)	−0.0215 (13)	−0.0087 (13)
C5	0.0402 (12)	0.0550 (14)	0.0486 (13)	0.0098 (10)	−0.0051 (10)	0.0043 (11)
C6	0.0561 (16)	0.0622 (16)	0.0702 (18)	0.0093 (13)	−0.0158 (13)	−0.0013 (13)
C7	0.0514 (16)	0.078 (2)	0.076 (2)	0.0039 (14)	−0.0219 (14)	0.0047 (15)
C8	0.0744 (19)	0.0564 (16)	0.102 (2)	0.0328 (14)	−0.0008 (17)	0.0082 (15)
C9	0.0532 (14)	0.0456 (13)	0.0621 (16)	0.0195 (11)	−0.0026 (12)	0.0029 (11)
C10	0.0544 (15)	0.0403 (13)	0.0832 (19)	0.0050 (11)	−0.0071 (13)	0.0090 (12)
C11	0.0362 (12)	0.0514 (14)	0.0801 (18)	0.0088 (10)	−0.0053 (12)	0.0038 (12)
C12	0.0410 (12)	0.0413 (12)	0.0499 (13)	0.0146 (9)	−0.0064 (10)	−0.0004 (10)
C13	0.0437 (13)	0.0444 (13)	0.0686 (16)	0.0110 (10)	0.0067 (11)	0.0083 (11)
C14	0.0425 (13)	0.0582 (15)	0.0762 (18)	0.0186 (11)	0.0098 (12)	0.0092 (13)
C15	0.0361 (11)	0.0441 (12)	0.0465 (13)	0.0128 (9)	−0.0003 (9)	0.0032 (10)
C16	0.0423 (12)	0.0470 (13)	0.0480 (13)	0.0139 (10)	−0.0027 (10)	0.0024 (10)
C17	0.0425 (12)	0.0469 (13)	0.0505 (14)	0.0174 (10)	−0.0013 (10)	0.0033 (10)
O1	0.145 (3)	0.0866 (18)	0.118 (2)	0.0498 (18)	−0.0214 (19)	−0.0214 (15)
N6	0.139 (3)	0.082 (2)	0.0782 (19)	0.0462 (19)	−0.0147 (18)	−0.0233 (15)
C18	0.160 (4)	0.078 (3)	0.089 (3)	0.018 (3)	−0.007 (3)	−0.014 (2)
C19	0.138 (4)	0.179 (5)	0.135 (4)	0.067 (4)	0.008 (3)	−0.026 (4)
C20	0.182 (5)	0.097 (3)	0.208 (6)	0.013 (4)	−0.058 (5)	−0.063 (4)

Geometric parameters (Å, º) top

C17—Cl1	1.734 (2)	C11—C12	1.370 (3)
N1—H1A	0.8600	C11—H11A	0.9300
N2—H2A	0.8600	C12—C13	1.367 (3)
C1—H1B	0.9600	C12—N2	1.430 (3)
C1—H1C	0.9600	C13—C14	1.380 (3)
C1—H1D	0.9600	C13—H13A	0.9300
C2—C3	1.368 (4)	C14—H14A	0.9300
C2—C7	1.377 (4)	C15—N3	1.329 (3)
C2—C1	1.507 (3)	C15—N2	1.339 (3)
C3—C4	1.387 (3)	C15—N5	1.358 (3)
C3—H3A	0.9300	C16—N1	1.335 (3)
C4—C5	1.373 (3)	C16—N3	1.336 (3)
C4—H4A	0.9300	C16—N4	1.359 (3)
C5—C6	1.375 (3)	C17—N4	1.300 (3)
C5—N1	1.403 (3)	C17—N5	1.315 (3)
C6—C7	1.376 (4)	O1—C18	1.279 (5)
C6—H6A	0.9300	N6—C18	1.297 (5)
C7—H7A	0.9300	N6—C20	1.400 (5)
C8—C9	1.509 (3)	N6—C19	1.468 (5)
C8—H8A	0.9600	C18—H18A	0.9300
C8—H8B	0.9600	C19—H19A	0.9600
C8—H8C	0.9600	C19—H19B	0.9600
C9—C10	1.369 (4)	C19—H19C	0.9600
C9—C14	1.375 (4)	C20—H20A	0.9600
C10—C11	1.379 (3)	C20—H20B	0.9600
C10—H10A	0.9300	C20—H20C	0.9600

N4—C17—Cl1	115.32 (17)	C13—C12—N2	121.5 (2)
N5—C17—Cl1	114.56 (17)	C11—C12—N2	119.4 (2)
C2—C1—H1B	109.5	C12—C13—C14	119.5 (2)
C2—C1—H1C	109.5	C12—C13—H13A	120.2
H1B—C1—H1C	109.5	C14—C13—H13A	120.2
C2—C1—H1D	109.5	C9—C14—C13	122.3 (2)
H1B—C1—H1D	109.5	C9—C14—H14A	118.8
H1C—C1—H1D	109.5	C13—C14—H14A	118.8
C3—C2—C7	116.7 (2)	N3—C15—N2	118.55 (19)
C3—C2—C1	121.9 (3)	N3—C15—N5	125.7 (2)
C7—C2—C1	121.4 (3)	N2—C15—N5	115.77 (19)
C2—C3—C4	122.2 (3)	N1—C16—N3	120.5 (2)
C2—C3—H3A	118.9	N1—C16—N4	114.4 (2)
C4—C3—H3A	118.9	N3—C16—N4	125.1 (2)
C5—C4—C3	120.4 (3)	N4—C17—N5	130.1 (2)
C5—C4—H4A	119.8	C16—N1—C5	131.2 (2)
C3—C4—H4A	119.8	C16—N1—H1A	114.4
C4—C5—C6	117.9 (2)	C5—N1—H1A	114.4
C4—C5—N1	125.7 (2)	C15—N2—C12	125.31 (18)
C6—C5—N1	116.4 (2)	C15—N2—H2A	117.3
C5—C6—C7	120.9 (3)	C12—N2—H2A	117.3
C5—C6—H6A	119.5	C15—N3—C16	114.60 (19)
C7—C6—H6A	119.5	C17—N4—C16	112.54 (19)
C6—C7—C2	121.9 (3)	C17—N5—C15	111.89 (19)
C6—C7—H7A	119.1	C18—N6—C20	124.6 (4)
C2—C7—H7A	119.1	C18—N6—C19	119.1 (4)
C9—C8—H8A	109.5	C20—N6—C19	116.2 (4)
C9—C8—H8B	109.5	O1—C18—N6	123.1 (4)
H8A—C8—H8B	109.5	O1—C18—H18A	118.5
C9—C8—H8C	109.5	N6—C18—H18A	118.5
H8A—C8—H8C	109.5	N6—C19—H19A	109.5
H8B—C8—H8C	109.5	N6—C19—H19B	109.5
C10—C9—C14	117.1 (2)	H19A—C19—H19B	109.5
C10—C9—C8	121.1 (2)	N6—C19—H19C	109.5
C14—C9—C8	121.8 (2)	H19A—C19—H19C	109.5
C9—C10—C11	121.3 (2)	H19B—C19—H19C	109.5
C9—C10—H10A	119.4	N6—C20—H20A	109.5
C11—C10—H10A	119.4	N6—C20—H20B	109.5
C12—C11—C10	120.7 (2)	H20A—C20—H20B	109.5
C12—C11—H11A	119.7	N6—C20—H20C	109.5
C10—C11—H11A	119.7	H20A—C20—H20C	109.5
C13—C12—C11	119.1 (2)	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.06	2.923 (3)	177
N2—H2A···N5ⁱ	0.86	2.24	3.081 (3)	168
C4—H4A···N3	0.93	2.30	2.905 (3)	122
C20—H20A···O1	0.96	2.39	2.792 (5)	105
C1—H1D···Cg1ⁱⁱ	0.96	2.86	3.653 (4)	145

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆ClN₅·C₃H₇NO
M_r	398.89
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.821 (2), 10.980 (2), 14.060 (3)
α, β, γ (°)	91.13 (3), 94.29 (2), 98.32 (4)
V (Å³)	1038.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5740, 3832, 2786
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.146, 1.02
No. of reflections	3832
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.24

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.06	2.923 (3)	177
N2—H2A···N5ⁱ	0.86	2.24	3.081 (3)	168
C4—H4A···N3	0.93	2.30	2.905 (3)	122
C20—H20A···O1	0.96	2.39	2.792 (5)	105
C1—H1D···Cg1ⁱⁱ	0.96	2.86	3.653 (4)	145

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x, −y+1, −z.

Acknowledgements

The authors would like to thank the Natural Science Foundation of Shandong Province (Nos. Y2006B08 and Z2007B01).

References

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