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In the title compound, C17H25N3OS, the mean plane of the imidazolinone system makes a dihedral angle of 83.07 (1)° with the phenyl ring. The crystal packing is stabilized by inter­molecular N—H...N and C—H...O hydrogen-bonding inter­actions. The hexyl group is disordered over two sites with approximate occupancy factors 0.7:0.3.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047228/at2411sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047228/at2411Isup2.hkl
Contains datablock I

CCDC reference: 667282

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.053
  • wR factor = 0.157
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.21 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.65 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT415_ALERT_2_C Short Inter D-H..H-X H1 .. H12A .. 2.12 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.60 Deg. C16' -C15 -C16 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.50 Deg. H15A -C15 -H15C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.20 Deg. H15B -C15 -H15D 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 16
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Imidazolinones are important heterocycles exhibiting remarkable biological activities, especially fungicidal activities (Khodair et al., 1998). Since a novel mitochondrial respiratory inhibitor (Fenamidone) was found to show high fungicidal activities, many other 2-alkylthio imidazolinones have been synthesized to evaluate their fungicidal activities (Bruhn et al., 1998). We obtained the title compound, (I), which may be used as a new precursor for obtaining bioactive molecules. The crystal structure of (I) is presented here.

Atom S1, N1 and the five-membered imidazolone ring are essentially planar. The C16 and C17 atoms, and the hydrogen atoms attached to C15, C16 and C17 are disordered over two sites, with refined occupancies of 0.309 (7) and 0.691 (7) (Fig. 1). The bond lengths involving atom C9 indicate a degree of electron delocalization (Yuan et al., 2006). As can be seen from the packing diagram (Fig. 2), intermolecular N—H···N and C—H···O hydrogen bondings (Table 1) link the molecules.

Related literature top

Imidazolinones have been prepared and their biological activities, especially their fungicidal activities, have been studied by Khodair et al. (1998) and Bruhn et al. (1998). For related literature, see: Yuan et al., 2006.

Experimental top

A mixture of 5,5-dimethyl-3-phenylamino-2-thioxo-4-imidazolidione (0.71 g, 3 mmol), hexyl bromide (0.50 g, 3 mmol) and solid potassium carbonate (0.83 g, 6 mmol) in CH3CN (15 ml) was stirred for 5 h at 323 K and was filtered. The filtrate was condensed, and the residue was recrystallized from diethyl ether and petroleum ether (1:3) to give the title compound (I) in yield of 83% (m.p. 355 K). Suitable crystals were obtained by slow evaporation of a solution of (I) in dichloromethane and petroleum ether at room temperature.

Refinement top

All H atoms were located in difference maps and treated as riding atoms, except those at N1, with the following distance restraints: C—H = 0.93 Å, Uiso = 1.2Ueq(C) for Csp2, C—H = 0.97 Å, Uiso = 1.2Ueq(C) for CH2, N—H = 0.86 Å, Uiso = 1.2Ueq(N) for NH2, C—H = 0.96 Å, Uiso = 1.5Ueq(C) for CH3.

Structure description top

Imidazolinones are important heterocycles exhibiting remarkable biological activities, especially fungicidal activities (Khodair et al., 1998). Since a novel mitochondrial respiratory inhibitor (Fenamidone) was found to show high fungicidal activities, many other 2-alkylthio imidazolinones have been synthesized to evaluate their fungicidal activities (Bruhn et al., 1998). We obtained the title compound, (I), which may be used as a new precursor for obtaining bioactive molecules. The crystal structure of (I) is presented here.

Atom S1, N1 and the five-membered imidazolone ring are essentially planar. The C16 and C17 atoms, and the hydrogen atoms attached to C15, C16 and C17 are disordered over two sites, with refined occupancies of 0.309 (7) and 0.691 (7) (Fig. 1). The bond lengths involving atom C9 indicate a degree of electron delocalization (Yuan et al., 2006). As can be seen from the packing diagram (Fig. 2), intermolecular N—H···N and C—H···O hydrogen bondings (Table 1) link the molecules.

Imidazolinones have been prepared and their biological activities, especially their fungicidal activities, have been studied by Khodair et al. (1998) and Bruhn et al. (1998). For related literature, see: Yuan et al., 2006.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme. Only the major disorder component is shown.
[Figure 2] Fig. 2. The packing in the crystal structure, showing the N—H···N and C—H···O hydrogen bonds as dashed lines.
1-Anilino-2-hexylsulfanyl-4,4-dimethyl-1H-imidazol-5(4H)-one top
Crystal data top
C17H25N3OSF(000) = 688
Mr = 319.46Dx = 1.192 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3820 reflections
a = 6.2528 (5) Åθ = 2.5–27.4°
b = 14.8770 (11) ŵ = 0.19 mm1
c = 19.1740 (15) ÅT = 292 K
β = 93.806 (1)°Block, colourless
V = 1779.7 (2) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4037 independent reflections
Radiation source: fine-focus sealed tube3099 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 85
Tmin = 0.964, Tmax = 0.982k = 1917
10984 measured reflectionsl = 2124
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0936P)2 + 0.0291P]
where P = (Fo2 + 2Fc2)/3
4037 reflections(Δ/σ)max < 0.001
222 parametersΔρmax = 0.49 e Å3
16 restraintsΔρmin = 0.44 e Å3
Crystal data top
C17H25N3OSV = 1779.7 (2) Å3
Mr = 319.46Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.2528 (5) ŵ = 0.19 mm1
b = 14.8770 (11) ÅT = 292 K
c = 19.1740 (15) Å0.20 × 0.20 × 0.10 mm
β = 93.806 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4037 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3099 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.982Rint = 0.037
10984 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05316 restraints
wR(F2) = 0.157H-atom parameters constrained
S = 1.06Δρmax = 0.49 e Å3
4037 reflectionsΔρmin = 0.44 e Å3
222 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*/UeqOcc. (<1)
N11.0843 (2)0.63981 (9)0.23056 (7)0.0404 (3)
H11.17010.62760.19860.049*
N20.8961 (2)0.68754 (9)0.21568 (8)0.0401 (3)
N30.5428 (2)0.70044 (9)0.18400 (8)0.0444 (4)
O10.9892 (2)0.82995 (9)0.25323 (9)0.0652 (4)
S10.72154 (8)0.53663 (3)0.16269 (3)0.04854 (19)
C10.9848 (3)0.62221 (14)0.35171 (11)0.0550 (5)
H1A0.85320.64990.34120.066*
C21.0374 (4)0.59096 (16)0.41849 (12)0.0708 (7)
H20.94030.59820.45280.085*
C31.2297 (4)0.54941 (17)0.43532 (12)0.0732 (7)
H31.26340.52870.48050.088*
C41.3712 (4)0.53891 (16)0.38448 (13)0.0697 (7)
H41.50200.51070.39530.084*
C51.3226 (3)0.56953 (14)0.31739 (11)0.0543 (5)
H51.42020.56150.28340.065*
C61.1288 (3)0.61219 (11)0.30042 (9)0.0408 (4)
C70.8579 (3)0.77681 (11)0.23033 (10)0.0449 (4)
C80.6195 (3)0.78913 (11)0.21235 (11)0.0498 (5)
C90.7054 (3)0.64835 (11)0.18752 (8)0.0374 (4)
C100.5790 (4)0.86296 (15)0.15830 (15)0.0820 (8)
H10A0.63860.84570.11540.123*
H10B0.64530.91770.17520.123*
H10C0.42740.87220.15010.123*
C110.5136 (3)0.80949 (17)0.28010 (15)0.0739 (7)
H11A0.36340.82030.26990.111*
H11B0.57870.86180.30180.111*
H11C0.53200.75910.31120.111*
C120.4533 (3)0.51978 (13)0.12390 (11)0.0532 (5)
H12A0.35190.52050.16000.064*
H12B0.41640.56810.09130.064*
C130.4406 (3)0.43057 (12)0.08595 (10)0.0483 (5)
H13A0.54350.43020.05030.058*
H13B0.47890.38270.11880.058*
C140.2194 (3)0.41275 (14)0.05226 (11)0.0574 (5)
H14A0.11640.41830.08770.069*
H14B0.18640.45890.01750.069*
C150.1907 (4)0.32247 (14)0.01789 (13)0.0706 (7)
H15A0.23090.27540.05120.085*0.691 (7)
H15B0.28260.31790.02080.085*0.691 (7)
H15C0.18750.27910.05560.085*0.309 (7)
H15D0.32160.31100.00500.085*0.309 (7)
C160.0461 (7)0.3103 (3)0.0092 (3)0.0754 (15)0.691 (7)
H16A0.13650.31780.02960.091*0.691 (7)
H16B0.08340.35710.04310.091*0.691 (7)
C170.0929 (7)0.2202 (3)0.0426 (3)0.0909 (17)0.691 (7)
H17A0.00610.20930.07790.136*0.691 (7)
H17B0.23660.21980.06360.136*0.691 (7)
H17C0.07780.17400.00770.136*0.691 (7)
C16'0.0146 (17)0.2957 (9)0.0348 (5)0.081 (4)0.309 (7)
H16C0.04100.34650.06200.097*0.309 (7)
H16D0.05890.24870.06580.097*0.309 (7)
C17'0.141 (2)0.2625 (10)0.0151 (7)0.120 (5)0.309 (7)
H17D0.06390.23870.05610.179*0.309 (7)
H17E0.22830.21610.00680.179*0.309 (7)
H17F0.23040.31120.02830.179*0.309 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0312 (7)0.0454 (8)0.0447 (8)0.0094 (6)0.0031 (6)0.0019 (6)
N20.0296 (7)0.0379 (7)0.0524 (9)0.0038 (6)0.0010 (6)0.0040 (6)
N30.0350 (8)0.0358 (7)0.0613 (9)0.0019 (6)0.0054 (7)0.0079 (6)
O10.0362 (8)0.0492 (8)0.1091 (12)0.0066 (6)0.0028 (7)0.0211 (8)
S10.0460 (3)0.0359 (3)0.0621 (3)0.00756 (19)0.0089 (2)0.00951 (19)
C10.0502 (12)0.0572 (12)0.0587 (12)0.0017 (9)0.0111 (9)0.0004 (9)
C20.0889 (19)0.0719 (15)0.0536 (13)0.0121 (13)0.0192 (12)0.0029 (11)
C30.0871 (19)0.0748 (15)0.0557 (13)0.0169 (13)0.0106 (13)0.0155 (11)
C40.0591 (14)0.0749 (15)0.0725 (15)0.0030 (11)0.0150 (11)0.0225 (11)
C50.0407 (11)0.0651 (12)0.0566 (11)0.0042 (9)0.0002 (9)0.0090 (9)
C60.0364 (9)0.0386 (9)0.0470 (10)0.0065 (7)0.0007 (7)0.0020 (7)
C70.0344 (9)0.0395 (9)0.0608 (11)0.0001 (7)0.0028 (8)0.0047 (8)
C80.0337 (9)0.0358 (9)0.0786 (13)0.0024 (7)0.0053 (9)0.0123 (8)
C90.0362 (9)0.0354 (8)0.0401 (9)0.0006 (7)0.0005 (7)0.0026 (7)
C100.0710 (16)0.0419 (11)0.129 (2)0.0058 (11)0.0260 (15)0.0086 (12)
C110.0382 (11)0.0704 (14)0.1143 (19)0.0057 (10)0.0140 (11)0.0458 (13)
C120.0461 (11)0.0480 (10)0.0640 (12)0.0049 (8)0.0088 (9)0.0175 (9)
C130.0530 (12)0.0397 (9)0.0513 (11)0.0012 (8)0.0042 (8)0.0066 (8)
C140.0524 (12)0.0529 (11)0.0658 (13)0.0040 (9)0.0058 (10)0.0104 (9)
C150.0780 (17)0.0515 (12)0.0792 (16)0.0100 (11)0.0187 (12)0.0076 (10)
C160.066 (3)0.068 (3)0.090 (4)0.005 (2)0.009 (2)0.028 (3)
C170.085 (3)0.078 (3)0.106 (3)0.025 (2)0.023 (2)0.018 (2)
C16'0.103 (7)0.081 (6)0.059 (5)0.016 (5)0.006 (5)0.018 (4)
C17'0.116 (9)0.102 (9)0.144 (10)0.019 (7)0.035 (8)0.007 (8)
Geometric parameters (Å, º) top
N1—N21.3878 (18)C11—H11C0.9600
N1—C61.411 (2)C12—C131.513 (2)
N1—H10.8600C12—H12A0.9700
N2—C71.382 (2)C12—H12B0.9700
N2—C91.403 (2)C13—C141.510 (3)
N3—C91.276 (2)C13—H13A0.9700
N3—C81.494 (2)C13—H13B0.9700
O1—C71.202 (2)C14—C151.502 (3)
S1—C91.7337 (16)C14—H14A0.9700
S1—C121.8063 (19)C14—H14B0.9700
C1—C21.381 (3)C15—C16'1.497 (7)
C1—C61.385 (2)C15—C161.547 (4)
C1—H1A0.9300C15—H15A0.9700
C2—C31.372 (3)C15—H15B0.9700
C2—H20.9300C15—H15C0.9700
C3—C41.368 (4)C15—H15D0.9700
C3—H30.9300C16—C171.506 (5)
C4—C51.379 (3)C16—H16A0.9700
C4—H40.9300C16—H16B0.9700
C5—C61.388 (3)C17—H17A0.9600
C5—H50.9300C17—H17B0.9600
C7—C81.519 (2)C17—H17C0.9600
C8—C101.520 (3)C16'—C17'1.493 (8)
C8—C111.527 (3)C16'—H16C0.9700
C10—H10A0.9600C16'—H16D0.9700
C10—H10B0.9600C17'—H17D0.9600
C10—H10C0.9600C17'—H17E0.9600
C11—H11A0.9600C17'—H17F0.9600
C11—H11B0.9600
N2—N1—C6117.06 (13)S1—C12—H12B109.7
N2—N1—H1121.5H12A—C12—H12B108.2
C6—N1—H1121.5C14—C13—C12112.16 (15)
C7—N2—N1127.29 (14)C14—C13—H13A109.2
C7—N2—C9108.89 (14)C12—C13—H13A109.2
N1—N2—C9123.64 (13)C14—C13—H13B109.2
C9—N3—C8106.38 (14)C12—C13—H13B109.2
C9—S1—C12100.18 (8)H13A—C13—H13B107.9
C2—C1—C6119.7 (2)C15—C14—C13115.09 (18)
C2—C1—H1A120.1C15—C14—H14A108.5
C6—C1—H1A120.1C13—C14—H14A108.5
C3—C2—C1121.4 (2)C15—C14—H14B108.5
C3—C2—H2119.3C13—C14—H14B108.5
C1—C2—H2119.3H14A—C14—H14B107.5
C4—C3—C2118.8 (2)C16'—C15—C14126.5 (6)
C4—C3—H3120.6C16'—C15—C1625.6 (4)
C2—C3—H3120.6C14—C15—C16109.6 (2)
C3—C4—C5120.9 (2)C16'—C15—H15A113.6
C3—C4—H4119.5C14—C15—H15A109.7
C5—C4—H4119.5C16—C15—H15A109.7
C4—C5—C6120.3 (2)C16'—C15—H15B85.0
C4—C5—H5119.8C14—C15—H15B109.7
C6—C5—H5119.8C16—C15—H15B109.7
C1—C6—C5118.79 (18)H15A—C15—H15B108.2
C1—C6—N1123.13 (17)C16'—C15—H15C106.0
C5—C6—N1118.02 (16)C14—C15—H15C106.0
O1—C7—N2125.69 (16)C16—C15—H15C96.1
O1—C7—C8129.81 (16)H15A—C15—H15C17.5
N2—C7—C8104.49 (14)H15B—C15—H15C124.4
N3—C8—C7105.20 (13)C16'—C15—H15D104.6
N3—C8—C10110.81 (17)C14—C15—H15D106.0
C7—C8—C10111.01 (17)C16—C15—H15D130.2
N3—C8—C11109.76 (16)H15A—C15—H15D88.9
C7—C8—C11107.78 (17)H15B—C15—H15D23.2
C10—C8—C11112.01 (19)H15C—C15—H15D106.3
N3—C9—N2114.94 (14)C17—C16—C15113.7 (3)
N3—C9—S1128.92 (13)C17—C16—H16A108.8
N2—C9—S1116.14 (12)C15—C16—H16A108.8
C8—C10—H10A109.5C17—C16—H16B108.8
C8—C10—H10B109.5C15—C16—H16B108.8
H10A—C10—H10B109.5H16A—C16—H16B107.7
C8—C10—H10C109.5C17'—C16'—C1597.8 (8)
H10A—C10—H10C109.5C17'—C16'—H16C112.2
H10B—C10—H10C109.5C15—C16'—H16C112.2
C8—C11—H11A109.5C17'—C16'—H16D112.2
C8—C11—H11B109.5C15—C16'—H16D112.2
H11A—C11—H11B109.5H16C—C16'—H16D109.8
C8—C11—H11C109.5C16'—C17'—H17D109.5
H11A—C11—H11C109.5C16'—C17'—H17E109.5
H11B—C11—H11C109.5H17D—C17'—H17E109.5
C13—C12—S1109.73 (13)C16'—C17'—H17F109.5
C13—C12—H12A109.7H17D—C17'—H17F109.5
S1—C12—H12A109.7H17E—C17'—H17F109.5
C13—C12—H12B109.7
C6—N1—N2—C776.7 (2)O1—C7—C8—C1058.3 (3)
C6—N1—N2—C997.85 (18)N2—C7—C8—C10122.80 (18)
C6—C1—C2—C30.4 (3)O1—C7—C8—C1164.7 (3)
C1—C2—C3—C40.1 (4)N2—C7—C8—C11114.19 (17)
C2—C3—C4—C50.1 (4)C8—N3—C9—N20.3 (2)
C3—C4—C5—C60.4 (4)C8—N3—C9—S1179.96 (14)
C2—C1—C6—C50.9 (3)C7—N2—C9—N32.3 (2)
C2—C1—C6—N1178.00 (18)N1—N2—C9—N3173.08 (15)
C4—C5—C6—C10.9 (3)C7—N2—C9—S1177.90 (12)
C4—C5—C6—N1178.14 (18)N1—N2—C9—S16.7 (2)
N2—N1—C6—C17.0 (2)C12—S1—C9—N35.03 (19)
N2—N1—C6—C5175.88 (15)C12—S1—C9—N2175.25 (13)
N1—N2—C7—O16.9 (3)C9—S1—C12—C13169.55 (14)
C9—N2—C7—O1177.93 (19)S1—C12—C13—C14179.94 (14)
N1—N2—C7—C8172.10 (15)C12—C13—C14—C15175.90 (19)
C9—N2—C7—C83.10 (19)C13—C14—C15—C16'162.4 (5)
C9—N3—C8—C71.6 (2)C13—C14—C15—C16175.6 (3)
C9—N3—C8—C10121.66 (19)C16'—C15—C16—C1746.1 (12)
C9—N3—C8—C11114.11 (18)C14—C15—C16—C17178.1 (4)
O1—C7—C8—N3178.2 (2)C14—C15—C16'—C17'89.9 (9)
N2—C7—C8—N32.88 (19)C16—C15—C16'—C17'35.1 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13B···O1i0.972.573.430 (2)148
N1—H1···N3ii0.862.603.189 (2)126
C11—H11A···O1iii0.962.343.299 (3)173
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1, y, z; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC17H25N3OS
Mr319.46
Crystal system, space groupMonoclinic, P21/n
Temperature (K)292
a, b, c (Å)6.2528 (5), 14.8770 (11), 19.1740 (15)
β (°) 93.806 (1)
V3)1779.7 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.964, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
10984, 4037, 3099
Rint0.037
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.157, 1.06
No. of reflections4037
No. of parameters222
No. of restraints16
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.44

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13B···O1i0.972.573.430 (2)147.6
N1—H1···N3ii0.862.603.189 (2)126.4
C11—H11A···O1iii0.962.343.299 (3)172.6
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1, y, z; (iii) x1, y, z.
 

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