Download citation
Download citation
link to html
The title compound, C21H20Cl2N2O2S, was synthesized as a potential reverse transcriptase (RT) inhibitor of the human immunodeficiency virus type 1 (HIV-1). Structural analysis confirms that the compound is present in the 3H-tautomeric form. A centrosymmetric dimer is formed in the crystal structure through pairs of N—H...O hydrogen bonds. The structure also displays C—H...Cl and C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034976/rz2158sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034976/rz2158Isup2.hkl
Contains datablock I

CCDC reference: 657828

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.069
  • wR factor = 0.222
  • Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.88 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.65 Ratio PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C17
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.19 PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 6.94 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 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

As part of an ongoing research work aimed at developing potent HIV-1 inhibitors, we have recently focused our attention on the structural modifications of dihydroalkoxybenzyloxopyrimidines (DABOs), one of the most interesting and representative classes of non-nucleoside reverse transcriptase inhibitors (NNRTIs). We have synthesized a series of 2-arylalkylsulfur-substituted DABOs analogues, including the title compound, (I), as potential HIV-1 inhibitors. According to the possible delocalization of the CN double bond in the pyrimidine ring, compound (I) could theoretically exist in three different tautomeric forms: the 1H-, the 3H-, and the aromatic form (Fig. 1). While NMR spectroscopy strongly indicated that the title compound adopted the 3H-tautomeric form, confirmations was sought using X-ray crystallography.

In the structure of (I), the carbonyl C—O bond length is 1.245 (4) Å, which is not significantly different from the value of 1.242 (3) Å found in 2-(cyclopentylsulfanyl)-6-(1-naphthoyl)-pyrimidin-4(3H)-one (Ji et al., 2006). Meanwhile, the lengths of C9—N1 and C9—N2 bonds are 1.344 (4) Å and 1.299 (4) Å, respectively. These values confirm that the title compound adopts the 3H-tautomeric form in the solid state (Fig. 2).

In the crystal structure, centrosymmetric dimers are formed by pairs of N1—H1···O2ii hydrogen bonds [symmetry code: (ii) -x, -y + 2, -z]. These dimers are further linked by weak C—H···O interactions (Table 1, Fig. 3).

Related literature top

For the crystal structure of a related pyrimidin-4(3H)-one, see: Ji et al. (2006).

Experimental top

To a stirred solution of 6-(2,6-dichlorobenzyl)-5-ethyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one (1 g, 3.17 mmol) in anhydrous DMF (18 ml) was added K2CO3 (0.53 g, 3.84 mmol) under a nitrogen atmosphere. The mixture was stirred at 298 K for 20 min, then 1-(bromomethyl)-4-methoxybenzene (0.60 g, 3.83 mmol) was added, and the reaction mixture was stirred at 298 K for 28 h. The reaction mixture was poured into cold H2O (100 ml), the resulting precipitate was collected by filtration, washed with water and recrystallized from butan-2-one (yield: 46%; m.p. 504.2–504.5 K). Single cystals of the title compound suitable for X-ray diffraction were grown by slow evaporation of a DMF solution. The product was characterized by IR, MS, 1H NMR and 13C NMR.

Refinement top

The H atom bound to N1 was located in a difference Fourier map and refined with a distance restraint of 0.86 (1) Å. All other H atoms were placed in geometrically idealized position and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. Methyl groups were allowed to rotate freely about the C—C bond.

Structure description top

As part of an ongoing research work aimed at developing potent HIV-1 inhibitors, we have recently focused our attention on the structural modifications of dihydroalkoxybenzyloxopyrimidines (DABOs), one of the most interesting and representative classes of non-nucleoside reverse transcriptase inhibitors (NNRTIs). We have synthesized a series of 2-arylalkylsulfur-substituted DABOs analogues, including the title compound, (I), as potential HIV-1 inhibitors. According to the possible delocalization of the CN double bond in the pyrimidine ring, compound (I) could theoretically exist in three different tautomeric forms: the 1H-, the 3H-, and the aromatic form (Fig. 1). While NMR spectroscopy strongly indicated that the title compound adopted the 3H-tautomeric form, confirmations was sought using X-ray crystallography.

In the structure of (I), the carbonyl C—O bond length is 1.245 (4) Å, which is not significantly different from the value of 1.242 (3) Å found in 2-(cyclopentylsulfanyl)-6-(1-naphthoyl)-pyrimidin-4(3H)-one (Ji et al., 2006). Meanwhile, the lengths of C9—N1 and C9—N2 bonds are 1.344 (4) Å and 1.299 (4) Å, respectively. These values confirm that the title compound adopts the 3H-tautomeric form in the solid state (Fig. 2).

In the crystal structure, centrosymmetric dimers are formed by pairs of N1—H1···O2ii hydrogen bonds [symmetry code: (ii) -x, -y + 2, -z]. These dimers are further linked by weak C—H···O interactions (Table 1, Fig. 3).

For the crystal structure of a related pyrimidin-4(3H)-one, see: Ji et al. (2006).

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. Possible tautomeric forms of the title compound.
[Figure 2] Fig. 2. The molecular structure of the title compound showing 30% probability of displacement ellipsoids and the atom-numbering scheme.
[Figure 3] Fig. 3. Packing diagram of the title compound viewed along the a axis. Thermal ellipsoids are drawn at the 30% probability level. Intermolecular N—H···O hydrogen bonds are shown as dashed lines.
6-(2,6-Dichlorobenzyl)-5-ethyl-2-(4-methoxybenzylsulfanyl)pyrimidin-4(3H)-one top
Crystal data top
C21H20Cl2N2O2SF(000) = 904
Mr = 435.35Dx = 1.334 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 946 reflections
a = 10.037 (3) Åθ = 2.4–19.2°
b = 17.264 (5) ŵ = 0.42 mm1
c = 13.006 (4) ÅT = 293 K
β = 105.901 (5)°Block, colourless
V = 2167.4 (12) Å30.20 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4733 independent reflections
Radiation source: fine-focus sealed tube2050 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 27.2°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.922, Tmax = 0.940k = 2121
10682 measured reflectionsl = 1416
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222H atoms treated by a mixture of independent and constrained refinement
S = 0.87 w = 1/[σ2(Fo2) + (0.1246P)2]
where P = (Fo2 + 2Fc2)/3
4733 reflections(Δ/σ)max < 0.001
259 parametersΔρmax = 0.79 e Å3
1 restraintΔρmin = 0.36 e Å3
Crystal data top
C21H20Cl2N2O2SV = 2167.4 (12) Å3
Mr = 435.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.037 (3) ŵ = 0.42 mm1
b = 17.264 (5) ÅT = 293 K
c = 13.006 (4) Å0.20 × 0.20 × 0.15 mm
β = 105.901 (5)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4733 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2050 reflections with I > 2σ(I)
Tmin = 0.922, Tmax = 0.940Rint = 0.050
10682 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0691 restraint
wR(F2) = 0.222H atoms treated by a mixture of independent and constrained refinement
S = 0.87Δρmax = 0.79 e Å3
4733 reflectionsΔρmin = 0.36 e Å3
259 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
Cl10.4124 (2)0.63842 (15)0.0284 (2)0.2158 (13)
Cl20.1444 (2)0.68614 (13)0.26805 (15)0.1606 (8)
N10.1198 (3)0.92035 (15)0.0294 (2)0.0535 (7)
N20.2527 (3)0.80811 (15)0.0714 (2)0.0565 (7)
O11.0343 (3)1.00550 (19)0.3657 (2)0.0954 (10)
O20.1101 (2)0.92001 (13)0.05248 (19)0.0621 (7)
S10.38515 (10)0.94244 (5)0.11803 (10)0.0775 (4)
C11.1372 (5)1.0113 (4)0.3105 (4)0.145 (3)
H1A1.15530.96090.28610.217*
H1B1.22071.03180.35760.217*
H1C1.10551.04520.25020.217*
C20.9086 (4)0.9743 (2)0.3126 (3)0.0639 (10)
C30.8719 (4)0.9551 (3)0.2074 (3)0.0863 (13)
H30.93300.96390.16620.104*
C40.7439 (4)0.9227 (3)0.1616 (3)0.0837 (13)
H40.71970.90980.08940.100*
C50.6523 (4)0.9091 (2)0.2194 (3)0.0645 (10)
C60.6893 (4)0.9330 (2)0.3243 (3)0.0652 (10)
H60.62640.92740.36460.078*
C70.8158 (4)0.9646 (2)0.3704 (3)0.0649 (10)
H70.83870.97960.44180.078*
C80.5162 (4)0.8701 (2)0.1694 (4)0.0775 (12)
H8A0.48980.83850.22220.093*
H8B0.52500.83660.11170.093*
C90.2405 (3)0.88306 (18)0.0689 (3)0.0545 (9)
C100.0018 (3)0.88240 (18)0.0153 (3)0.0519 (8)
C110.0061 (3)0.79882 (18)0.0140 (3)0.0529 (8)
C120.1330 (4)0.76667 (18)0.0313 (3)0.0523 (8)
C130.1228 (4)0.7540 (2)0.0637 (4)0.0788 (12)
H13A0.17960.78360.12300.095*
H13B0.09740.70610.09250.095*
C140.2057 (6)0.7353 (4)0.0102 (6)0.149 (3)
H14A0.15240.70310.06690.223*
H14B0.28810.70820.02770.223*
H14C0.23070.78230.03970.223*
C150.1547 (4)0.67980 (19)0.0402 (3)0.0621 (10)
H15A0.07580.65580.05690.074*
H15B0.16050.65950.02800.074*
C160.2846 (4)0.65926 (18)0.1253 (4)0.0668 (11)
C170.4062 (5)0.6412 (3)0.1025 (6)0.111 (2)
C180.5284 (9)0.6259 (5)0.1810 (11)0.179 (5)
H180.60960.61350.16330.215*
C190.5249 (13)0.6295 (5)0.2816 (12)0.202 (7)
H190.60670.62110.33500.242*
C200.4118 (10)0.6443 (4)0.3100 (7)0.168 (4)
H200.41370.64290.38180.202*
C210.2899 (6)0.6619 (3)0.2338 (5)0.1020 (16)
H10.112 (3)0.9696 (6)0.034 (2)0.052 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.178 (2)0.227 (2)0.307 (3)0.0219 (17)0.177 (2)0.089 (2)
Cl20.1943 (19)0.1909 (17)0.1253 (14)0.0393 (15)0.0923 (13)0.0251 (12)
N10.0436 (17)0.0386 (15)0.072 (2)0.0006 (12)0.0052 (14)0.0033 (14)
N20.0438 (16)0.0430 (15)0.076 (2)0.0018 (12)0.0059 (14)0.0002 (14)
O10.0632 (18)0.143 (3)0.0700 (18)0.0409 (18)0.0010 (14)0.0038 (18)
O20.0438 (14)0.0544 (14)0.0789 (17)0.0035 (11)0.0011 (12)0.0029 (12)
S10.0474 (6)0.0494 (5)0.1179 (9)0.0064 (4)0.0075 (5)0.0015 (5)
C10.068 (3)0.265 (8)0.099 (4)0.071 (4)0.019 (3)0.014 (5)
C20.050 (2)0.080 (2)0.054 (2)0.0116 (19)0.0014 (17)0.0017 (19)
C30.063 (3)0.133 (4)0.063 (3)0.020 (3)0.019 (2)0.011 (3)
C40.063 (3)0.124 (4)0.057 (2)0.011 (3)0.003 (2)0.022 (2)
C50.043 (2)0.061 (2)0.081 (3)0.0001 (16)0.0021 (19)0.002 (2)
C60.050 (2)0.072 (2)0.072 (3)0.0005 (18)0.0140 (19)0.009 (2)
C70.063 (2)0.074 (2)0.053 (2)0.0082 (19)0.0096 (19)0.0013 (19)
C80.046 (2)0.060 (2)0.109 (3)0.0023 (18)0.008 (2)0.000 (2)
C90.045 (2)0.0464 (19)0.067 (2)0.0030 (15)0.0074 (16)0.0016 (16)
C100.043 (2)0.0508 (19)0.059 (2)0.0008 (16)0.0085 (16)0.0040 (16)
C110.0436 (19)0.0478 (18)0.064 (2)0.0055 (15)0.0087 (16)0.0037 (16)
C120.052 (2)0.0465 (17)0.059 (2)0.0032 (15)0.0162 (17)0.0041 (16)
C130.046 (2)0.057 (2)0.126 (4)0.0074 (18)0.010 (2)0.005 (2)
C140.100 (5)0.131 (5)0.224 (8)0.029 (4)0.060 (5)0.040 (5)
C150.061 (2)0.0440 (18)0.080 (3)0.0027 (16)0.019 (2)0.0100 (18)
C160.054 (2)0.0361 (17)0.106 (3)0.0002 (16)0.014 (2)0.003 (2)
C170.061 (3)0.065 (3)0.212 (7)0.006 (2)0.045 (4)0.005 (3)
C180.072 (5)0.086 (4)0.365 (16)0.023 (3)0.038 (9)0.009 (8)
C190.123 (8)0.083 (5)0.333 (17)0.010 (5)0.050 (12)0.077 (9)
C200.168 (7)0.129 (6)0.151 (6)0.046 (6)0.050 (7)0.068 (5)
C210.117 (4)0.079 (3)0.094 (4)0.025 (3)0.000 (3)0.022 (3)
Geometric parameters (Å, º) top
Cl1—C171.720 (7)C7—H70.9300
Cl2—C211.692 (6)C8—H8A0.9700
N1—C91.344 (4)C8—H8B0.9700
N1—C101.366 (4)C10—C111.445 (4)
N1—H10.858 (10)C11—C121.367 (5)
N2—C91.299 (4)C11—C131.494 (5)
N2—C121.372 (4)C12—C151.515 (5)
O1—C21.372 (4)C13—C141.470 (7)
O1—C11.414 (5)C13—H13A0.9700
O2—C101.245 (4)C13—H13B0.9700
S1—C91.749 (3)C14—H14A0.9600
S1—C81.804 (4)C14—H14B0.9600
C1—H1A0.9600C14—H14C0.9600
C1—H1B0.9600C15—C161.504 (5)
C1—H1C0.9600C15—H15A0.9700
C2—C31.357 (5)C15—H15B0.9700
C2—C71.358 (5)C16—C171.369 (6)
C3—C41.378 (5)C16—C211.398 (6)
C3—H30.9300C17—C181.390 (11)
C4—C51.358 (5)C18—C191.320 (15)
C4—H40.9300C18—H180.9300
C5—C61.375 (5)C19—C201.311 (13)
C5—C81.501 (5)C19—H190.9300
C6—C71.361 (5)C20—C211.381 (9)
C6—H60.9300C20—H200.9300
C9—N1—C10122.6 (3)C12—C11—C10116.9 (3)
C9—N1—H1123 (2)C12—C11—C13124.8 (3)
C10—N1—H1115 (2)C10—C11—C13118.3 (3)
C9—N2—C12116.3 (3)C11—C12—N2124.6 (3)
C2—O1—C1118.1 (3)C11—C12—C15122.1 (3)
C9—S1—C8100.25 (17)N2—C12—C15113.3 (3)
O1—C1—H1A109.5C14—C13—C11114.1 (4)
O1—C1—H1B109.5C14—C13—H13A108.7
H1A—C1—H1B109.5C11—C13—H13A108.7
O1—C1—H1C109.5C14—C13—H13B108.7
H1A—C1—H1C109.5C11—C13—H13B108.7
H1B—C1—H1C109.5H13A—C13—H13B107.6
C3—C2—C7119.4 (4)C13—C14—H14A109.5
C3—C2—O1124.1 (3)C13—C14—H14B109.5
C7—C2—O1116.5 (3)H14A—C14—H14B109.5
C2—C3—C4119.8 (4)C13—C14—H14C109.5
C2—C3—H3120.1H14A—C14—H14C109.5
C4—C3—H3120.1H14B—C14—H14C109.5
C5—C4—C3121.6 (4)C16—C15—C12111.5 (3)
C5—C4—H4119.2C16—C15—H15A109.3
C3—C4—H4119.2C12—C15—H15A109.3
C4—C5—C6117.2 (3)C16—C15—H15B109.3
C4—C5—C8120.7 (4)C12—C15—H15B109.3
C6—C5—C8122.1 (4)H15A—C15—H15B108.0
C7—C6—C5121.6 (3)C17—C16—C21115.9 (5)
C7—C6—H6119.2C17—C16—C15122.6 (5)
C5—C6—H6119.2C21—C16—C15121.4 (4)
C2—C7—C6120.3 (4)C16—C17—C18122.9 (7)
C2—C7—H7119.9C16—C17—Cl1119.8 (5)
C6—C7—H7119.9C18—C17—Cl1117.2 (6)
C5—C8—S1109.6 (3)C19—C18—C17117.5 (11)
C5—C8—H8A109.8C19—C18—H18121.3
S1—C8—H8A109.8C17—C18—H18121.3
C5—C8—H8B109.8C20—C19—C18123.2 (13)
S1—C8—H8B109.8C20—C19—H19118.4
H8A—C8—H8B108.2C18—C19—H19118.4
N2—C9—N1123.8 (3)C19—C20—C21120.5 (11)
N2—C9—S1120.7 (3)C19—C20—H20119.8
N1—C9—S1115.5 (2)C21—C20—H20119.8
O2—C10—N1119.9 (3)C20—C21—C16119.8 (7)
O2—C10—C11124.4 (3)C20—C21—Cl2121.7 (6)
N1—C10—C11115.7 (3)C16—C21—Cl2118.5 (4)
C1—O1—C2—C36.3 (7)C10—C11—C12—N22.6 (5)
C1—O1—C2—C7175.5 (5)C13—C11—C12—N2176.1 (3)
C7—C2—C3—C43.1 (7)C10—C11—C12—C15178.5 (3)
O1—C2—C3—C4178.7 (4)C13—C11—C12—C152.9 (5)
C2—C3—C4—C50.1 (7)C9—N2—C12—C112.8 (5)
C3—C4—C5—C63.6 (7)C9—N2—C12—C15178.1 (3)
C3—C4—C5—C8177.0 (4)C12—C11—C13—C1491.8 (5)
C4—C5—C6—C74.0 (6)C10—C11—C13—C1489.6 (5)
C8—C5—C6—C7176.6 (3)C11—C12—C15—C16159.2 (3)
C3—C2—C7—C62.7 (6)N2—C12—C15—C1621.7 (4)
O1—C2—C7—C6179.0 (3)C12—C15—C16—C1799.4 (4)
C5—C6—C7—C21.0 (6)C12—C15—C16—C2176.8 (4)
C4—C5—C8—S192.8 (4)C21—C16—C17—C180.4 (7)
C6—C5—C8—S186.6 (4)C15—C16—C17—C18176.8 (5)
C9—S1—C8—C5178.5 (3)C21—C16—C17—Cl1178.6 (3)
C12—N2—C9—N10.4 (5)C15—C16—C17—Cl12.2 (5)
C12—N2—C9—S1179.8 (2)C16—C17—C18—C190.3 (13)
C10—N1—C9—N22.2 (5)Cl1—C17—C18—C19178.6 (8)
C10—N1—C9—S1177.7 (3)C17—C18—C19—C202.2 (17)
C8—S1—C9—N23.9 (4)C18—C19—C20—C214.1 (16)
C8—S1—C9—N1176.2 (3)C19—C20—C21—C164.0 (10)
C9—N1—C10—O2178.6 (3)C19—C20—C21—Cl2176.6 (7)
C9—N1—C10—C112.3 (5)C17—C16—C21—C202.2 (6)
O2—C10—C11—C12179.1 (3)C15—C16—C21—C20178.6 (4)
N1—C10—C11—C120.0 (5)C17—C16—C21—Cl2178.4 (3)
O2—C10—C11—C132.1 (5)C15—C16—C21—Cl22.0 (5)
N1—C10—C11—C13178.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15B···Cl10.972.563.043 (4)111
C7—H7···O1i0.932.493.389 (5)162
N1—H1···O2ii0.86 (1)1.92 (1)2.777 (4)175 (3)
Symmetry codes: (i) x+2, y+2, z+1; (ii) x, y+2, z.

Experimental details

Crystal data
Chemical formulaC21H20Cl2N2O2S
Mr435.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.037 (3), 17.264 (5), 13.006 (4)
β (°) 105.901 (5)
V3)2167.4 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.20 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.922, 0.940
No. of measured, independent and
observed [I > 2σ(I)] reflections
10682, 4733, 2050
Rint0.050
(sin θ/λ)max1)0.642
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.222, 0.87
No. of reflections4733
No. of parameters259
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.79, 0.36

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
C15—H15B···Cl10.972.563.043 (4)111.1
C7—H7···O1i0.932.493.389 (5)161.9
N1—H1···O2ii0.858 (10)1.921 (11)2.777 (4)175 (3)
Symmetry codes: (i) x+2, y+2, z+1; (ii) x, y+2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds