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In the title compound, C20H21ClN4OS·C3H7NO, the mol­ecules are linked to each other through an N—H...O hydrogen bond to form chains to which the dimethyl­formamide solvent mol­ecules are attached via a second N—H...O inter­action. Bond lengths and angles are unexceptional.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023094/bg2045sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023094/bg2045Isup2.hkl
Contains datablock I

CCDC reference: 651478

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.059
  • wR factor = 0.184
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level A EXPT005_ALERT_1_A _exptl_crystal_description is missing Crystal habit description. The following tests will not be performed. CRYSR_01
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.40 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.89 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 44
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Substituted 1,2,4-triazoles have received much attention on account of their important pharmacological activites, such as antiviral, analgesic, antimicrobial, antidepressant and antifungal effect (Sughen & Yoloye, 1978; Cansiz et al.,2001; Kane et al., 1988). Based on the excellent properties of substituted 1,2,4-triazole, we attempted to incorporate 2-(4-chlorophenyl)-3-methylbutanoic acid into the triazole ring system, hoping to find for a novel triazole compound with higher bioactivity. We report here the synthesis and crystal structure of the title compound (I), obtained during this process (Scheme 1).

There are three aromatic rings in the structure, namely a triazole (N1 N3/C12/C13), a methylbenzene (C14 C20), and a chlorobenzene (C1 C6) rings, (Fig 1). The p-methylbenzene and 4-chlorobenzene planes make a dihedral angle of 38.2 (5)°, while the 1,2,4-triazole ring forms dihedral angles of 31.5 (0)° and 68.3 (1)° with the p-methylbenzene and 4-chlorobenzene rings, respectively. Bonds and angles in (I) are unexceptional.

The molecules link to each other into chains through a N—H···O hydrogen bond; in turn, the dimethylformamide solvato molecules are attached to these one-dimensional structures via a second N—H···O interaction (Table 2 and Figures 1 and 2).

Related literature top

For related literature, see: Cansiz et al. (2001); Kane et al. (1988); Reid & Heindel (1976); Sughen & Yoloye (1978); Zhang et al. (1990).

Experimental top

3-aryl-4-amino -5-mercapto-1,2,4-triazole was prepared by the literature method (Zhang et al., 1990; Reid & Heindel, 1976). 2-(4-chlorophenyl)-3-methylbutanoic acid (0.01 mol) and sulfuric chloride (10 ml) were placed in a dried round-bottomed flask containing a magnetic stirrer bar and stirred at 75°C for 1.5 h. Then the excessive sulfuric chloride was removed under reduced pressure, and the residue left to cool to room temperature to obtain the 2-(4-chlorophenyl)-3-methylbutanoyl chloride. Then 3-aryl-4-amino-5-mercapto-1,2,4-triazole (0.008 mol) and 20 ml anhydrous acetonitrile were added. The reaction mixture was stirred at refluxed temperature and monitored by TLC. After refluxing for 3 h, the undisolved by-products were removed by filtration immediately and the product (I) precipitated from the filtrate when the solution was cooled to room temperature. It was further purified by recrystallization in ethanol. Crystals suitable for single-crystal X-ray diffraction were obtained by cooling the hot solution of N,N'-dimethylformamide. 1H NMR (DMSO-d6, 400 MHz): 11.30 (s, 1H, NH), 7.92–7.00 (m, 8H, Ph—H), 3.76 (d, 1H, —C—H), 3.00 (s, 1H, S—H), 2.52 (m, 1H, —C—H), 2.35 (s, 3H, Ph—CH3), 1.10 (d, 6H, —CH3); Analysis calculated for C20H21ClN4OS: C 59.91, H 5.28, N 13.97%; found: C 59.97, H 5.25, N 14.00%.

Refinement top

The H atoms were positioned geometrically (C—H = 0.93, 0.96 or 0.98 A ° and N—H = 0.86 A °) and refined using the riding-model approximation, with Uiso(H) = 1.2Ueq(C, N).

Structure description top

Substituted 1,2,4-triazoles have received much attention on account of their important pharmacological activites, such as antiviral, analgesic, antimicrobial, antidepressant and antifungal effect (Sughen & Yoloye, 1978; Cansiz et al.,2001; Kane et al., 1988). Based on the excellent properties of substituted 1,2,4-triazole, we attempted to incorporate 2-(4-chlorophenyl)-3-methylbutanoic acid into the triazole ring system, hoping to find for a novel triazole compound with higher bioactivity. We report here the synthesis and crystal structure of the title compound (I), obtained during this process (Scheme 1).

There are three aromatic rings in the structure, namely a triazole (N1 N3/C12/C13), a methylbenzene (C14 C20), and a chlorobenzene (C1 C6) rings, (Fig 1). The p-methylbenzene and 4-chlorobenzene planes make a dihedral angle of 38.2 (5)°, while the 1,2,4-triazole ring forms dihedral angles of 31.5 (0)° and 68.3 (1)° with the p-methylbenzene and 4-chlorobenzene rings, respectively. Bonds and angles in (I) are unexceptional.

The molecules link to each other into chains through a N—H···O hydrogen bond; in turn, the dimethylformamide solvato molecules are attached to these one-dimensional structures via a second N—H···O interaction (Table 2 and Figures 1 and 2).

For related literature, see: Cansiz et al. (2001); Kane et al. (1988); Reid & Heindel (1976); Sughen & Yoloye (1978); Zhang et al. (1990).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. The hydrogen bond linking the molecule and the solvate is shown in dashed line. Displacement ellipsoids drawn at a 30% level. Symmetry code (i): x,y,z + 1
[Figure 2] Fig. 2. View of the molecular chain in (I). Hydrogen bonds are shown as dashed lines.
4-[2-(4-Chlorophenyl)-3-methylbutanamido]-3-p-tolyl-1H-1,2,4- triazole-5(4H)-thione dimethylformamide solvate top
Crystal data top
C20H21ClN4OS·C3H7NOF(000) = 1000
Mr = 474.01Dx = 1.207 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 846 reflections
a = 10.235 (4) Åθ = 2.3–22.5°
b = 26.654 (12) ŵ = 0.25 mm1
c = 9.581 (4) ÅT = 298 K
β = 93.963 (6)°, colourless
V = 2607.6 (19) Å30.30 × 0.15 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
5098 independent reflections
Radiation source: fine-focus sealed tube2828 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
phi and ω scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1212
Tmin = 0.918, Tmax = 0.975k = 3228
11679 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.1043P)2]
where P = (Fo2 + 2Fc2)/3
5098 reflections(Δ/σ)max < 0.001
292 parametersΔρmax = 0.35 e Å3
44 restraintsΔρmin = 0.26 e Å3
Crystal data top
C20H21ClN4OS·C3H7NOV = 2607.6 (19) Å3
Mr = 474.01Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.235 (4) ŵ = 0.25 mm1
b = 26.654 (12) ÅT = 298 K
c = 9.581 (4) Å0.30 × 0.15 × 0.10 mm
β = 93.963 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5098 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2828 reflections with I > 2σ(I)
Tmin = 0.918, Tmax = 0.975Rint = 0.043
11679 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05944 restraints
wR(F2) = 0.184H-atom parameters constrained
S = 0.96Δρmax = 0.35 e Å3
5098 reflectionsΔρmin = 0.26 e Å3
292 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
xyzUiso*/Ueq
Cl10.16930 (14)0.00080 (4)0.83559 (14)0.1301 (5)
S10.11276 (10)0.38390 (3)0.82591 (9)0.0871 (3)
N10.4180 (2)0.31509 (10)1.0000 (3)0.0740 (7)
N20.3445 (3)0.35624 (10)0.9613 (3)0.0757 (7)
H2B0.36850.38630.98300.091*
N30.2390 (2)0.29481 (8)0.8760 (2)0.0573 (6)
N40.1380 (2)0.26553 (8)0.8176 (2)0.0538 (5)
H4A0.12740.26200.72830.065*
O10.07115 (17)0.24620 (7)1.02859 (16)0.0613 (5)
C10.1062 (3)0.06002 (11)0.8322 (4)0.0793 (9)
C20.0941 (3)0.08607 (12)0.7078 (3)0.0765 (8)
H2A0.11950.07150.62570.092*
C30.0440 (3)0.13405 (11)0.7068 (3)0.0634 (7)
H3A0.03610.15180.62300.076*
C40.0052 (2)0.15647 (10)0.8272 (3)0.0532 (6)
C50.0201 (3)0.12912 (11)0.9516 (3)0.0689 (8)
H5A0.00350.14371.03450.083*
C60.0690 (3)0.08105 (12)0.9537 (3)0.0817 (9)
H6A0.07670.06301.03690.098*
C70.0459 (2)0.21000 (10)0.8247 (2)0.0516 (6)
H7A0.05410.22100.72690.062*
C80.1804 (3)0.21674 (12)0.8848 (3)0.0694 (8)
H8A0.17250.20710.98380.083*
C90.2240 (3)0.27065 (14)0.8745 (4)0.0927 (11)
H9A0.30710.27410.91410.139*
H9B0.23210.28060.77800.139*
H9C0.16050.29160.92480.139*
C100.2807 (3)0.18231 (16)0.8079 (5)0.1045 (13)
H10A0.36420.18640.84650.157*
H10B0.25270.14810.81860.157*
H10C0.28830.19090.71040.157*
C110.0567 (2)0.24256 (9)0.9014 (2)0.0474 (6)
C120.2323 (3)0.34601 (11)0.8871 (3)0.0642 (7)
C130.3519 (2)0.27690 (10)0.9485 (3)0.0580 (7)
C140.3873 (2)0.22500 (11)0.9720 (3)0.0599 (7)
C150.4576 (3)0.21229 (13)1.0973 (3)0.0738 (8)
H15A0.48210.23731.16150.089*
C160.4902 (3)0.16410 (14)1.1260 (4)0.0909 (10)
H16A0.53580.15651.21070.109*
C170.4573 (4)0.12548 (14)1.0319 (5)0.0932 (11)
C180.4923 (6)0.07157 (18)1.0685 (7)0.161 (2)
H18A0.46110.05000.99330.241*
H18B0.45240.06221.15240.241*
H18C0.58570.06841.08300.241*
C190.3902 (3)0.13830 (13)0.9060 (4)0.0860 (10)
H19A0.36820.11330.84090.103*
C200.3556 (3)0.18687 (11)0.8756 (3)0.0684 (8)
H20A0.31090.19450.79050.082*
C210.5479 (7)0.4571 (2)0.1282 (8)0.166 (2)
H21A0.52740.47450.20800.199*
C220.7078 (11)0.4277 (6)0.0050 (10)0.317 (6)
H22A0.63830.42830.06760.476*
H22B0.72420.39370.03440.476*
H22C0.78570.44160.02980.476*
C230.7667 (9)0.4766 (3)0.2044 (15)0.319 (6)
H23A0.72780.50290.25620.479*
H23B0.83480.49050.15210.479*
H23C0.80310.45170.26810.479*
N50.6730 (5)0.45505 (15)0.1142 (6)0.1469 (17)
O20.4539 (5)0.44186 (13)0.0628 (6)0.209 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1782 (12)0.0764 (7)0.1362 (10)0.0280 (6)0.0133 (8)0.0057 (6)
S10.1223 (8)0.0741 (5)0.0620 (5)0.0057 (5)0.0142 (5)0.0044 (4)
N10.0710 (15)0.0752 (17)0.0742 (17)0.0165 (13)0.0059 (13)0.0077 (13)
N20.0882 (18)0.0666 (16)0.0709 (16)0.0202 (14)0.0050 (14)0.0068 (13)
N30.0638 (14)0.0640 (14)0.0435 (12)0.0132 (11)0.0007 (10)0.0030 (10)
N40.0629 (13)0.0659 (13)0.0317 (10)0.0124 (10)0.0016 (9)0.0028 (9)
O10.0723 (12)0.0795 (12)0.0319 (9)0.0013 (9)0.0020 (8)0.0017 (8)
C10.091 (2)0.0603 (18)0.086 (2)0.0022 (15)0.0001 (18)0.0009 (17)
C20.091 (2)0.076 (2)0.064 (2)0.0011 (17)0.0115 (16)0.0098 (16)
C30.0729 (18)0.0675 (18)0.0500 (16)0.0069 (14)0.0044 (13)0.0027 (13)
C40.0482 (14)0.0645 (16)0.0466 (15)0.0098 (12)0.0015 (11)0.0006 (12)
C50.083 (2)0.0725 (19)0.0516 (17)0.0048 (15)0.0051 (14)0.0009 (14)
C60.105 (2)0.075 (2)0.065 (2)0.0041 (18)0.0004 (17)0.0130 (16)
C70.0475 (14)0.0705 (16)0.0365 (13)0.0047 (12)0.0004 (10)0.0020 (11)
C80.0513 (16)0.100 (2)0.0573 (17)0.0042 (15)0.0107 (13)0.0022 (15)
C90.067 (2)0.114 (3)0.097 (3)0.0212 (19)0.0097 (18)0.004 (2)
C100.0508 (18)0.132 (3)0.130 (3)0.0175 (19)0.007 (2)0.009 (2)
C110.0509 (14)0.0570 (14)0.0342 (13)0.0073 (11)0.0024 (10)0.0011 (11)
C120.086 (2)0.0645 (17)0.0422 (14)0.0117 (15)0.0037 (13)0.0023 (12)
C130.0538 (15)0.0719 (18)0.0482 (15)0.0135 (14)0.0035 (12)0.0069 (13)
C140.0496 (15)0.0718 (18)0.0585 (17)0.0064 (13)0.0051 (12)0.0030 (14)
C150.0668 (19)0.090 (2)0.0641 (19)0.0027 (16)0.0001 (15)0.0052 (16)
C160.091 (2)0.093 (3)0.088 (2)0.010 (2)0.0011 (19)0.013 (2)
C170.080 (2)0.078 (2)0.122 (3)0.0071 (18)0.010 (2)0.012 (2)
C180.172 (5)0.090 (3)0.216 (6)0.016 (3)0.016 (4)0.017 (3)
C190.0636 (19)0.074 (2)0.119 (3)0.0026 (16)0.0008 (19)0.017 (2)
C200.0490 (15)0.077 (2)0.079 (2)0.0031 (13)0.0018 (14)0.0107 (16)
C210.164 (5)0.124 (4)0.201 (6)0.014 (4)0.055 (5)0.012 (4)
C220.317 (12)0.489 (18)0.146 (7)0.141 (11)0.015 (7)0.023 (7)
C230.211 (7)0.139 (5)0.576 (17)0.011 (5)0.202 (10)0.043 (8)
N50.143 (4)0.094 (3)0.196 (5)0.006 (3)0.047 (4)0.011 (3)
O20.230 (4)0.111 (3)0.268 (5)0.069 (3)0.103 (4)0.015 (3)
Geometric parameters (Å, º) top
Cl1—C11.744 (3)C9—H9C0.9600
S1—C121.662 (3)C10—H10A0.9600
N1—C131.301 (3)C10—H10B0.9600
N1—N21.367 (3)C10—H10C0.9600
N2—C121.336 (4)C13—C141.443 (4)
N2—H2B0.8600C14—C201.396 (4)
N3—C121.371 (4)C14—C151.397 (4)
N3—N41.382 (3)C15—C161.351 (5)
N3—C131.391 (3)C15—H15A0.9300
N4—C111.343 (3)C16—C171.394 (5)
N4—H4A0.8600C16—H16A0.9300
O1—C111.221 (3)C17—C191.389 (5)
C1—C61.370 (5)C17—C181.516 (6)
C1—C21.378 (4)C18—H18A0.9600
C2—C31.378 (4)C18—H18B0.9600
C2—H2A0.9300C18—H18C0.9600
C3—C41.382 (4)C19—C201.368 (4)
C3—H3A0.9300C19—H19A0.9300
C4—C51.397 (4)C20—H20A0.9300
C4—C71.519 (4)C21—O21.183 (7)
C5—C61.375 (4)C21—N51.298 (7)
C5—H5A0.9300C21—H21A0.9300
C6—H6A0.9300C22—N51.343 (10)
C7—C111.514 (3)C22—H22A0.9600
C7—C81.539 (4)C22—H22B0.9600
C7—H7A0.9800C22—H22C0.9600
C8—C91.506 (5)C23—N51.373 (8)
C8—C101.528 (5)C23—H23A0.9600
C8—H8A0.9800C23—H23B0.9600
C9—H9A0.9600C23—H23C0.9600
C9—H9B0.9600
C13—N1—N2105.2 (2)O1—C11—N4121.5 (2)
C12—N2—N1114.7 (2)O1—C11—C7124.2 (2)
C12—N2—H2B122.7N4—C11—C7114.1 (2)
N1—N2—H2B122.7N2—C12—N3101.5 (2)
C12—N3—N4123.6 (2)N2—C12—S1130.4 (2)
C12—N3—C13110.3 (2)N3—C12—S1128.1 (2)
N4—N3—C13125.5 (2)N1—C13—N3108.3 (2)
C11—N4—N3119.50 (19)N1—C13—C14124.9 (3)
C11—N4—H4A120.3N3—C13—C14126.7 (2)
N3—N4—H4A120.3C20—C14—C15118.3 (3)
C6—C1—C2121.0 (3)C20—C14—C13123.4 (3)
C6—C1—Cl1119.3 (3)C15—C14—C13118.4 (3)
C2—C1—Cl1119.7 (3)C16—C15—C14120.7 (3)
C1—C2—C3119.0 (3)C16—C15—H15A119.6
C1—C2—H2A120.5C14—C15—H15A119.6
C3—C2—H2A120.5C15—C16—C17121.7 (4)
C2—C3—C4121.6 (3)C15—C16—H16A119.2
C2—C3—H3A119.2C17—C16—H16A119.2
C4—C3—H3A119.2C19—C17—C16117.6 (3)
C3—C4—C5117.8 (3)C19—C17—C18121.9 (4)
C3—C4—C7120.8 (2)C16—C17—C18120.5 (4)
C5—C4—C7121.4 (2)C17—C18—H18A109.5
C6—C5—C4121.1 (3)C17—C18—H18B109.5
C6—C5—H5A119.4H18A—C18—H18B109.5
C4—C5—H5A119.4C17—C18—H18C109.5
C1—C6—C5119.4 (3)H18A—C18—H18C109.5
C1—C6—H6A120.3H18B—C18—H18C109.5
C5—C6—H6A120.3C20—C19—C17121.5 (3)
C11—C7—C4107.71 (19)C20—C19—H19A119.2
C11—C7—C8111.1 (2)C17—C19—H19A119.2
C4—C7—C8114.8 (2)C19—C20—C14120.2 (3)
C11—C7—H7A107.7C19—C20—H20A119.9
C4—C7—H7A107.7C14—C20—H20A119.9
C8—C7—H7A107.7O2—C21—N5134.6 (8)
C9—C8—C10110.8 (3)O2—C21—H21A112.7
C9—C8—C7110.8 (2)N5—C21—H21A112.7
C10—C8—C7109.8 (2)N5—C22—H22A109.5
C9—C8—H8A108.5N5—C22—H22B109.5
C10—C8—H8A108.5H22A—C22—H22B109.5
C7—C8—H8A108.5N5—C22—H22C109.5
C8—C9—H9A109.5H22A—C22—H22C109.5
C8—C9—H9B109.5H22B—C22—H22C109.5
H9A—C9—H9B109.5N5—C23—H23A109.5
C8—C9—H9C109.5N5—C23—H23B109.5
H9A—C9—H9C109.5H23A—C23—H23B109.5
H9B—C9—H9C109.5N5—C23—H23C109.5
C8—C10—H10A109.5H23A—C23—H23C109.5
C8—C10—H10B109.5H23B—C23—H23C109.5
H10A—C10—H10B109.5C21—N5—C22114.8 (8)
C8—C10—H10C109.5C21—N5—C23124.7 (8)
H10A—C10—H10C109.5C22—N5—C23120.4 (9)
H10B—C10—H10C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O2i0.861.862.694 (4)164
N4—H4A···O1ii0.861.972.824 (3)170
Symmetry codes: (i) x, y, z+1; (ii) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC20H21ClN4OS·C3H7NO
Mr474.01
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)10.235 (4), 26.654 (12), 9.581 (4)
β (°) 93.963 (6)
V3)2607.6 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.30 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.918, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
11679, 5098, 2828
Rint0.043
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.184, 0.96
No. of reflections5098
No. of parameters292
No. of restraints44
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.26

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O2i0.861.862.694 (4)164.1
N4—H4A···O1ii0.861.972.824 (3)170.3
Symmetry codes: (i) x, y, z+1; (ii) x, y+1/2, z1/2.
 

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