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The title compound, C22H20ClN3O3S·1.5C6H6, was synthesized by the intermolecular [3 + 2]-cyclo­addition of azomethine yl­ide, derived from isatin and sarcosine by a de­carboxyl­ative route, and 5-(4-chloro­benzyl­idene)-3-ethyl­thia­zolidine-2,4-dione. In the mol­ecule of the title compound, an approximately planar 2-ox­indole system, a pyrrolidine ring in an envelope conformation, and a planar thia­zolidine ring are joined via two spiro-junctions. The mol­ecules in the crystal are linked by an intermolecular N—H...N hydrogen bond [N...N = 3.071 (3) Å], forming infinite chains running along the c axis. One of the solvate benzene mol­ecules occupies a special position on an inversion centre.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018804/ya6172sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018804/ya6172Isup2.hkl
Contains datablock I

CCDC reference: 222916

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in solvent or counterion
  • R factor = 0.057
  • wR factor = 0.155
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98
Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.237 Value of mu given = 0.240 ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.796 0.923 Tmin' and Tmax expected: 0.902 0.922 RR' = 0.882 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 6 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C13 PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... C27 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C30 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C23 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C26 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Spiro-compounds represent an important class of naturally occurring substances, which in many cases exhibit interesting biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are widely used for the construction of spiro-compounds (Caramella & Grunanger, 1984). In this paper, the structure of the title compound, (I), is reported. The compound was synthesized by the intermolecular [3 + 2]-cycloaddition of azomethine ylide, derived from isatin and sarcosine by a decarboxylative route, and 5-(4-chloro-benzylidene)-3-ethylthiazolidine-2,4-dione.

The molecular structure of (I) is shown in Fig. 1. The molecule involves a chain of 2-oxindole, pyrrolidine, and thiazolidine moieties, joined via two spiro-junctions. The pyrrolidine ring N2—C5—C4—C3—C6 has an envelope conformation; atom N2 is displaced by 0.618 (3) Å from the mean plane of the C5/C4/C3/C6 atoms [plane A; maximum deviation of the C4 atom is 0.031 (3) Å]. The C5/N2/C6 plane forms a dihedral angle of 135.6 (2)° with plane A, whereas the dihedral angle of the latter with the mean plane of the phenyl ring (C10–C15) is 76.7 (3)°. Both bicyclic indole system and thiazolidine ring are almost planar [maximum deviations of atoms C17 and C2 from their respective mean planes are 0.035 (3) and 0.041 (4) Å]; their planes are approximately orthogonal to the bottom plane of the pyrrolidine cycle (plane A); the dihedral angles are equal to 78.3 (2) and 88.7 (3)°, respectively. Atoms O1 and O2 are displaced from the mean plane of the thiazolidine cycle by 0.027 (2) and −0.155 (2) Å, respectively.

There is one `active' H atom in the molecule which participates in the intermolecular N3—H3···N2i hydrogen bond [symmetry code: (i) x, −y + 1/2, z − 1/2] (Table 1). This hydrogen bond links the molecules of (I) in the crystal into infinite chains running along the c axis of the crystal (Fig. 2).

Experimental top

A mixture of 5-(4-chlorobenzylidene)-3-ethylthiazolidine-2,4-dione (2 mmol), prepared according to Lo et al. (1958), isatin (2 mmol), and sarcosine (2 mmol) was refluxed in dioxane (30 ml) until the disappearance of the starting material (as monitored by thin-layer chromatography). When the reaction was complete, the solvent was removed in vacuo and the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate 5:1) to give the title compound, (I). M.p. 476 K; IR (KBr): 3358.3 (–NH), 1750.2, 1718.7, 1685.9 (CO) cm−1; 1H NMR (CDCl3, p.p.m.): 0.87 (t, 3H, CH3), 2.26 (s, 3H, N—CH3), 3.40–3.50 (m, 2H, –CH2), 3.61 (dd, J = 9.3, 7.8 Hz, 1H, Hc), 4.03 (dd, J = 10.2, 9.3 Hz, 1H), 4.58 (dd, J = 10.2, 7.8 Hz, 1H), 6.82–7.38 (m, 8H, ArH), 7.41 (br, 1H, –NH); 13C NMR (p.p.m.): 12.68, 35.18, 36.95, 51.33, 58.29, 72.12, 79.90, 110.31, 123.13, 123.22, 127.01, 128.81, 130.61, 131.46,133.69,136.16, 142.39, 169.38, 175.42, 177.50. 20 mg of (I) was dissolved in 15 ml of benzene andthe solution was kept at room temperature for 15 d. Slow evaporation of the solvent gave colorless single crystals of (I) suitable for X-ray analysis.

Refinement top

All H atoms were placed in calculated positions, with C—H distances ranging from 0.93 to 0.98 Å and an N—H distance of 0.86 Å. They were included in the refinement in the riding-motion approximation, with Uiso = 1.2 (1.5 for methyl) times Ueq of the carrier atom. Both solvate benzene molecules refined poorly. In the final model, the benzene molecule in the general position was included with the fixed geometry of a regular hexagon (C—C = 1.39 Å). The solvate benzene molecule in the inversion centre was represented as two-component disorder with approximately equal occupancy factors, which refined to 0.49 (3) and 0.51 (3). The bond lengths in both components of the disordered benzene were constrained to 1.39±0.01 Å.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I); displacement ellipsoids are drawn at the 30% probability level, H atoms have been omitted and solvate benzene molecules are not shown.
[Figure 2] Fig. 2. The crystal packing diagram for (I), viewed along the a axis. All H atoms, with the exception of atom H3, participating in the hydrogen bond, have been omitted. The hydrogen bonds are shown as dashed lines.
4'-(4-Chlorophenyl)-3''-ethyl-1'-methyl-1H-indole-3-spiro-2'-pyrrolidine- 3'-spiro-5''-[1,3]thiazole-2(3H),2''(3''H),4''(5''H)-trione benzene sesquisolvate top
Crystal data top
C22H20ClN3O3S·1.5C6H6F(000) = 1172
Mr = 559.08Dx = 1.266 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.132 (3) ÅCell parameters from 886 reflections
b = 22.785 (7) Åθ = 2.7–23.1°
c = 12.515 (4) ŵ = 0.24 mm1
β = 112.477 (5)°T = 293 K
V = 2933.2 (15) Å3Parallelepiped, colorless
Z = 40.42 × 0.40 × 0.34 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
5070 independent reflections
Radiation source: fine-focus sealed tube2701 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1213
Tmin = 0.796, Tmax = 0.923k = 2715
14461 measured reflectionsl = 1414
Refinement top
Refinement on F2180 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.057 w = 1/[σ2(Fo2) + (0.084P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.155(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.27 e Å3
5070 reflectionsΔρmin = 0.23 e Å3
370 parameters
Crystal data top
C22H20ClN3O3S·1.5C6H6V = 2933.2 (15) Å3
Mr = 559.08Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.132 (3) ŵ = 0.24 mm1
b = 22.785 (7) ÅT = 293 K
c = 12.515 (4) Å0.42 × 0.40 × 0.34 mm
β = 112.477 (5)°
Data collection top
Bruker SMART CCD area detector
diffractometer
5070 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
2701 reflections with I > 2σ(I)
Tmin = 0.796, Tmax = 0.923Rint = 0.046
14461 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057180 restraints
wR(F2) = 0.155H-atom parameters constrained
S = 1.02Δρmax = 0.27 e Å3
5070 reflectionsΔρmin = 0.23 e Å3
370 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)
Cl10.11610 (11)0.08563 (6)0.13037 (15)0.1291 (6)
S10.47701 (9)0.13010 (4)0.05396 (7)0.0594 (3)
N10.6453 (3)0.06854 (14)0.1099 (3)0.0637 (8)
N20.5755 (3)0.25291 (12)0.1866 (2)0.0503 (7)
N30.6599 (3)0.25950 (14)0.0504 (3)0.0663 (9)
H30.65460.27540.11430.080*
O10.5867 (3)0.03034 (14)0.0726 (3)0.0990 (10)
O20.6643 (2)0.11726 (12)0.2731 (2)0.0693 (7)
O30.4440 (3)0.26401 (12)0.07717 (19)0.0672 (7)
C10.5791 (4)0.06809 (18)0.0070 (4)0.0678 (11)
C20.6206 (3)0.11421 (16)0.1690 (3)0.0525 (9)
C30.5314 (3)0.16081 (15)0.0914 (2)0.0467 (8)
C40.4222 (3)0.17704 (15)0.1376 (3)0.0498 (8)
H40.44780.15890.21410.060*
C50.4373 (3)0.24282 (15)0.1574 (3)0.0557 (9)
H5A0.38520.26420.08820.067*
H5B0.41210.25470.22030.067*
C60.6081 (3)0.22009 (14)0.1005 (2)0.0460 (8)
C70.5563 (4)0.25067 (16)0.0208 (3)0.0538 (9)
C80.7316 (4)0.01967 (19)0.1680 (4)0.0923 (14)
H8A0.69430.01690.13030.111*
H8B0.73950.01740.24780.111*
C90.8621 (5)0.0278 (3)0.1643 (5)0.1184 (18)
H9A0.85500.02720.08540.178*
H9B0.91850.00330.20640.178*
H9C0.89740.06480.19870.178*
C100.2874 (3)0.15539 (16)0.0676 (3)0.0544 (9)
C110.2412 (4)0.10599 (18)0.1058 (4)0.0721 (11)
H110.29410.08720.17340.086*
C120.1179 (4)0.08474 (19)0.0446 (4)0.0854 (13)
H120.08800.05180.07080.102*
C130.0402 (4)0.11219 (19)0.0541 (4)0.0763 (12)
C140.0815 (4)0.1606 (2)0.0946 (3)0.0714 (11)
H140.02710.17910.16200.086*
C150.2062 (4)0.18181 (18)0.0335 (3)0.0629 (10)
H150.23550.21440.06130.075*
C160.6115 (4)0.31501 (16)0.1955 (3)0.0715 (11)
H16A0.70310.31850.21310.107*
H16B0.59120.33300.25590.107*
H16C0.56390.33420.12340.107*
C170.7520 (3)0.21671 (14)0.1265 (3)0.0492 (8)
C180.7759 (4)0.24002 (17)0.0339 (3)0.0584 (9)
C190.8984 (4)0.2430 (2)0.0345 (4)0.0840 (13)
H190.91270.25790.02870.101*
C201.0003 (4)0.2236 (2)0.1307 (4)0.0866 (13)
H201.08440.22520.13200.104*
C210.9803 (4)0.20171 (18)0.2249 (4)0.0724 (11)
H211.05030.18910.28970.087*
C220.8551 (4)0.19856 (16)0.2228 (3)0.0577 (9)
H220.84100.18420.28660.069*
C230.0341 (7)0.1077 (3)0.5916 (7)0.180 (3)
H23A0.03230.11370.61820.216*
C240.1618 (9)0.1210 (3)0.6621 (4)0.176 (3)
H24A0.18080.13590.73600.212*
C250.2610 (5)0.1121 (3)0.6223 (6)0.166 (3)
H25A0.34640.12100.66950.199*
C260.2326 (7)0.0898 (3)0.5119 (6)0.174 (3)
H26A0.29900.08380.48530.209*
C270.1049 (9)0.0765 (3)0.4413 (4)0.243 (5)
H27A0.08590.06160.36750.292*
C280.0057 (5)0.0854 (3)0.4812 (7)0.217 (4)
H28A0.07980.07650.43390.261*
C290.410 (2)0.0334 (9)0.4133 (18)0.103 (6)0.51 (3)
H29A0.35250.05670.35540.124*0.51 (3)
C300.482 (3)0.0091 (10)0.3855 (10)0.088 (5)0.51 (3)
H30A0.46830.01630.30850.106*0.51 (3)
C310.576 (2)0.0411 (11)0.472 (2)0.109 (6)0.51 (3)
H31A0.62930.06750.45430.131*0.51 (3)
C29'0.404 (2)0.0430 (10)0.473 (3)0.113 (6)0.49 (3)
H29B0.33960.07140.45610.135*0.49 (3)
C30'0.430 (2)0.0158 (15)0.3852 (11)0.104 (6)0.49 (3)
H30B0.38470.02660.30870.125*0.49 (3)
C31'0.524 (3)0.0273 (11)0.412 (2)0.094 (5)0.49 (3)
H31B0.54010.04620.35250.112*0.49 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0599 (7)0.0985 (10)0.1858 (14)0.0080 (7)0.0011 (8)0.0142 (10)
S10.0606 (6)0.0695 (6)0.0469 (5)0.0056 (5)0.0191 (4)0.0109 (5)
N10.0547 (19)0.057 (2)0.072 (2)0.0044 (16)0.0167 (17)0.0023 (17)
N20.0579 (18)0.0563 (19)0.0434 (15)0.0043 (15)0.0268 (13)0.0077 (13)
N30.076 (2)0.081 (2)0.0568 (18)0.0037 (18)0.0412 (18)0.0177 (16)
O10.090 (2)0.086 (2)0.118 (2)0.0016 (18)0.0364 (18)0.047 (2)
O20.0662 (16)0.086 (2)0.0552 (16)0.0067 (14)0.0222 (13)0.0222 (14)
O30.0706 (18)0.086 (2)0.0480 (14)0.0125 (15)0.0261 (14)0.0139 (13)
C10.055 (2)0.061 (3)0.092 (3)0.011 (2)0.033 (2)0.019 (2)
C20.045 (2)0.061 (2)0.055 (2)0.0047 (18)0.0219 (18)0.0080 (19)
C30.052 (2)0.055 (2)0.0359 (17)0.0016 (17)0.0198 (15)0.0010 (15)
C40.050 (2)0.062 (2)0.0421 (18)0.0044 (17)0.0220 (16)0.0105 (16)
C50.064 (2)0.064 (2)0.0477 (19)0.003 (2)0.0309 (17)0.0018 (17)
C60.054 (2)0.051 (2)0.0376 (16)0.0045 (16)0.0233 (15)0.0023 (15)
C70.065 (2)0.057 (2)0.050 (2)0.002 (2)0.0326 (19)0.0014 (17)
C80.065 (3)0.065 (3)0.132 (4)0.012 (2)0.022 (3)0.003 (3)
C90.074 (3)0.108 (4)0.151 (5)0.016 (3)0.018 (3)0.017 (3)
C100.049 (2)0.061 (2)0.059 (2)0.0076 (18)0.0272 (18)0.0092 (19)
C110.050 (2)0.069 (3)0.093 (3)0.007 (2)0.023 (2)0.028 (2)
C120.058 (3)0.066 (3)0.128 (4)0.000 (2)0.031 (3)0.027 (3)
C130.048 (2)0.063 (3)0.106 (3)0.001 (2)0.017 (2)0.003 (3)
C140.053 (2)0.077 (3)0.076 (3)0.012 (2)0.015 (2)0.011 (2)
C150.059 (2)0.070 (3)0.060 (2)0.002 (2)0.024 (2)0.0121 (19)
C160.095 (3)0.057 (3)0.074 (3)0.011 (2)0.045 (2)0.016 (2)
C170.057 (2)0.051 (2)0.0437 (19)0.0049 (17)0.0243 (18)0.0081 (16)
C180.063 (2)0.067 (3)0.054 (2)0.005 (2)0.033 (2)0.0016 (19)
C190.077 (3)0.111 (4)0.085 (3)0.002 (3)0.054 (3)0.009 (3)
C200.063 (3)0.110 (4)0.100 (3)0.003 (3)0.045 (3)0.008 (3)
C210.058 (3)0.082 (3)0.073 (3)0.001 (2)0.020 (2)0.012 (2)
C220.060 (2)0.063 (2)0.053 (2)0.0067 (19)0.0247 (19)0.0075 (18)
C230.148 (7)0.206 (9)0.183 (9)0.041 (6)0.061 (6)0.032 (7)
C240.179 (8)0.190 (8)0.171 (7)0.011 (7)0.079 (7)0.052 (6)
C250.184 (8)0.151 (6)0.154 (7)0.046 (6)0.057 (6)0.024 (5)
C260.187 (8)0.209 (8)0.126 (6)0.043 (7)0.059 (6)0.008 (6)
C270.201 (10)0.330 (13)0.130 (7)0.060 (10)0.013 (7)0.077 (7)
C280.146 (7)0.297 (12)0.141 (8)0.025 (7)0.020 (6)0.033 (8)
C290.137 (13)0.065 (11)0.106 (12)0.016 (8)0.045 (11)0.006 (11)
C300.110 (16)0.060 (12)0.086 (7)0.019 (9)0.028 (8)0.003 (7)
C310.133 (14)0.102 (13)0.070 (12)0.018 (9)0.014 (11)0.021 (11)
C29'0.132 (14)0.092 (12)0.137 (18)0.004 (10)0.078 (15)0.011 (16)
C30'0.115 (12)0.088 (17)0.122 (10)0.032 (10)0.060 (10)0.004 (11)
C31'0.101 (15)0.087 (14)0.101 (13)0.035 (10)0.047 (12)0.007 (11)
Geometric parameters (Å, º) top
Cl1—C131.742 (4)C15—H150.9300
S1—C11.767 (4)C16—H16A0.9600
S1—C31.823 (3)C16—H16B0.9600
N1—C11.363 (5)C16—H16C0.9600
N1—C21.364 (4)C17—C221.373 (5)
N1—C81.469 (5)C17—C181.390 (4)
N2—C51.457 (4)C18—C191.362 (5)
N2—C161.463 (4)C19—C201.374 (6)
N2—C61.466 (4)C19—H190.9300
N3—C71.354 (4)C20—C211.375 (6)
N3—C181.391 (5)C20—H200.9300
N3—H30.8600C21—C221.385 (5)
O1—C11.214 (4)C21—H210.9300
O2—C21.206 (4)C22—H220.9300
O3—C71.216 (4)C23—C241.3900
C2—C31.523 (5)C23—C281.3900
C3—C41.577 (4)C23—H23A0.9300
C3—C61.578 (5)C24—C251.3900
C4—C101.502 (5)C24—H24A0.9300
C4—C51.518 (5)C25—C261.3900
C4—H40.9800C25—H25A0.9300
C5—H5A0.9700C26—C271.3900
C5—H5B0.9700C26—H26A0.9300
C6—C171.510 (4)C27—C281.3900
C6—C71.566 (5)C27—H27A0.9300
C8—C91.483 (6)C28—H28A0.9300
C8—H8A0.9700C29—C301.385 (8)
C8—H8B0.9700C29—C31i1.390 (9)
C9—H9A0.9600C29—H29A0.9300
C9—H9B0.9600C30—C311.392 (9)
C9—H9C0.9600C30—H30A0.9300
C10—C151.381 (5)C31—C29i1.390 (9)
C10—C111.396 (5)C31—H31A0.9300
C11—C121.378 (5)C29'—C30'1.390 (9)
C11—H110.9300C29'—C31'i1.398 (9)
C12—C131.360 (6)C29'—H29B0.9300
C12—H120.9300C30'—C31'1.380 (9)
C13—C141.366 (6)C30'—H30B0.9300
C14—C151.390 (5)C31'—C29'i1.398 (9)
C14—H140.9300C31'—H31B0.9300
C1—S1—C392.79 (18)C13—C14—C15118.9 (4)
C1—N1—C2116.7 (3)C13—C14—H14120.5
C1—N1—C8120.5 (3)C15—C14—H14120.5
C2—N1—C8122.6 (3)C10—C15—C14121.2 (4)
C5—N2—C16113.8 (3)C10—C15—H15119.4
C5—N2—C6105.6 (2)C14—C15—H15119.4
C16—N2—C6114.3 (2)N2—C16—H16A109.5
C7—N3—C18112.7 (3)N2—C16—H16B109.5
C7—N3—H3123.7H16A—C16—H16B109.5
C18—N3—H3123.7N2—C16—H16C109.5
O1—C1—N1125.6 (4)H16A—C16—H16C109.5
O1—C1—S1122.9 (4)H16B—C16—H16C109.5
N1—C1—S1111.5 (3)C22—C17—C18119.0 (3)
O2—C2—N1123.2 (3)C22—C17—C6131.8 (3)
O2—C2—C3123.0 (3)C18—C17—C6109.1 (3)
N1—C2—C3113.8 (3)C19—C18—C17121.7 (4)
C2—C3—C4109.6 (2)C19—C18—N3128.7 (3)
C2—C3—C6110.4 (3)C17—C18—N3109.6 (3)
C4—C3—C6104.1 (3)C18—C19—C20118.6 (4)
C2—C3—S1104.8 (2)C18—C19—H19120.7
C4—C3—S1116.6 (2)C20—C19—H19120.7
C6—C3—S1111.39 (19)C19—C20—C21121.2 (4)
C10—C4—C5116.3 (3)C19—C20—H20119.4
C10—C4—C3116.6 (3)C21—C20—H20119.4
C5—C4—C3103.8 (3)C20—C21—C22119.6 (4)
C10—C4—H4106.5C20—C21—H21120.2
C5—C4—H4106.5C22—C21—H21120.2
C3—C4—H4106.5C17—C22—C21119.9 (3)
N2—C5—C4103.7 (3)C17—C22—H22120.0
N2—C5—H5A111.0C21—C22—H22120.0
C4—C5—H5A111.0C24—C23—C28120.0
N2—C5—H5B111.0C24—C23—H23A120.0
C4—C5—H5B111.0C28—C23—H23A120.0
H5A—C5—H5B109.0C25—C24—C23120.0
N2—C6—C17114.0 (3)C25—C24—H24A120.0
N2—C6—C7112.5 (3)C23—C24—H24A120.0
C17—C6—C7101.4 (2)C26—C25—C24120.0
N2—C6—C3102.2 (2)C26—C25—H25A120.0
C17—C6—C3118.1 (3)C24—C25—H25A120.0
C7—C6—C3108.8 (3)C25—C26—C27120.0
O3—C7—N3126.8 (3)C25—C26—H26A120.0
O3—C7—C6126.1 (3)C27—C26—H26A120.0
N3—C7—C6107.2 (3)C28—C27—C26120.0
N1—C8—C9110.7 (4)C28—C27—H27A120.0
N1—C8—H8A109.5C26—C27—H27A120.0
C9—C8—H8A109.5C27—C28—C23120.0
N1—C8—H8B109.5C27—C28—H28A120.0
C9—C8—H8B109.5C23—C28—H28A120.0
H8A—C8—H8B108.1C30—C29—C31i120.1 (9)
C8—C9—H9A109.5C30—C29—H29A120.0
C8—C9—H9B109.5C31i—C29—H29A120.0
H9A—C9—H9B109.5C29—C30—C31120.2 (9)
C8—C9—H9C109.5C29—C30—H30A119.9
H9A—C9—H9C109.5C31—C30—H30A119.9
H9B—C9—H9C109.5C29i—C31—C30119.5 (9)
C15—C10—C11117.9 (3)C29i—C31—H31A120.3
C15—C10—C4123.3 (3)C30—C31—H31A120.3
C11—C10—C4118.8 (3)C30'—C29'—C31'i119.5 (9)
C12—C11—C10120.8 (4)C30'—C29'—H29B120.2
C12—C11—H11119.6C31'i—C29'—H29B120.2
C10—C11—H11119.6C31'—C30'—C29'119.8 (9)
C13—C12—C11119.7 (4)C31'—C30'—H30B120.1
C13—C12—H12120.1C29'—C30'—H30B120.1
C11—C12—H12120.1C30'—C31'—C29'i120.7 (9)
C12—C13—C14121.4 (4)C30'—C31'—H31B119.6
C12—C13—Cl1119.6 (4)C29'i—C31'—H31B119.6
C14—C13—Cl1119.0 (3)
C2—N1—C1—O1178.2 (4)N2—C6—C7—N3123.5 (3)
C8—N1—C1—O12.2 (6)C17—C6—C7—N31.3 (3)
C2—N1—C1—S11.3 (4)C3—C6—C7—N3124.0 (3)
C8—N1—C1—S1177.3 (3)C1—N1—C8—C984.4 (5)
C3—S1—C1—O1177.9 (3)C2—N1—C8—C999.8 (5)
C3—S1—C1—N12.6 (3)C5—C4—C10—C1544.9 (4)
C1—N1—C2—O2173.7 (3)C3—C4—C10—C1578.2 (4)
C8—N1—C2—O22.3 (5)C5—C4—C10—C11135.4 (3)
C1—N1—C2—C35.7 (4)C3—C4—C10—C11101.6 (4)
C8—N1—C2—C3178.4 (3)C15—C10—C11—C120.5 (6)
O2—C2—C3—C446.6 (4)C4—C10—C11—C12179.7 (4)
N1—C2—C3—C4132.8 (3)C10—C11—C12—C130.1 (7)
O2—C2—C3—C667.5 (4)C11—C12—C13—C140.1 (7)
N1—C2—C3—C6113.1 (3)C11—C12—C13—Cl1179.4 (3)
O2—C2—C3—S1172.4 (3)C12—C13—C14—C150.4 (6)
N1—C2—C3—S16.9 (3)Cl1—C13—C14—C15179.9 (3)
C1—S1—C3—C25.2 (2)C11—C10—C15—C141.1 (5)
C1—S1—C3—C4126.5 (3)C4—C10—C15—C14179.2 (3)
C1—S1—C3—C6114.2 (2)C13—C14—C15—C101.0 (6)
C2—C3—C4—C10107.6 (3)N2—C6—C17—C2253.5 (5)
C6—C3—C4—C10134.3 (3)C7—C6—C17—C22174.7 (4)
S1—C3—C4—C1011.2 (4)C3—C6—C17—C2266.6 (5)
C2—C3—C4—C5123.1 (3)N2—C6—C17—C18122.6 (3)
C6—C3—C4—C55.0 (3)C7—C6—C17—C181.4 (3)
S1—C3—C4—C5118.1 (3)C3—C6—C17—C18117.4 (3)
C16—N2—C5—C4172.7 (3)C22—C17—C18—C192.8 (6)
C6—N2—C5—C446.5 (3)C6—C17—C18—C19179.4 (4)
C10—C4—C5—N2159.6 (2)C22—C17—C18—N3175.6 (3)
C3—C4—C5—N230.2 (3)C6—C17—C18—N31.0 (4)
C5—N2—C6—C17170.7 (3)C7—N3—C18—C19178.4 (4)
C16—N2—C6—C1763.5 (4)C7—N3—C18—C170.2 (4)
C5—N2—C6—C774.5 (3)C17—C18—C19—C201.4 (6)
C16—N2—C6—C751.4 (4)N3—C18—C19—C20176.6 (4)
C5—N2—C6—C342.0 (3)C18—C19—C20—C210.3 (7)
C16—N2—C6—C3167.9 (3)C19—C20—C21—C220.7 (7)
C2—C3—C6—N296.1 (3)C18—C17—C22—C212.3 (5)
C4—C3—C6—N221.5 (3)C6—C17—C22—C21178.0 (3)
S1—C3—C6—N2147.9 (2)C20—C21—C22—C170.6 (6)
C2—C3—C6—C1729.9 (3)C28—C23—C24—C250.0
C4—C3—C6—C17147.5 (3)C23—C24—C25—C260.0
S1—C3—C6—C1786.1 (3)C24—C25—C26—C270.0
C2—C3—C6—C7144.7 (3)C25—C26—C27—C280.0
C4—C3—C6—C797.7 (3)C26—C27—C28—C230.0
S1—C3—C6—C728.7 (3)C24—C23—C28—C270.0
C18—N3—C7—O3179.1 (4)C31i—C29—C30—C315 (4)
C18—N3—C7—C60.7 (4)C29—C30—C31—C29i5 (4)
N2—C6—C7—O356.3 (5)C31'i—C29'—C30'—C31'2 (5)
C17—C6—C7—O3178.5 (3)C29'—C30'—C31'—C29'i2 (5)
C3—C6—C7—O356.2 (4)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N2ii0.862.393.071 (3)136
Symmetry code: (ii) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC22H20ClN3O3S·1.5C6H6
Mr559.08
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.132 (3), 22.785 (7), 12.515 (4)
β (°) 112.477 (5)
V3)2933.2 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.42 × 0.40 × 0.34
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.796, 0.923
No. of measured, independent and
observed [I > 2σ(I)] reflections
14461, 5070, 2701
Rint0.046
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.155, 1.02
No. of reflections5070
No. of parameters370
No. of restraints180
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.23

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N2i0.862.393.071 (3)136
Symmetry code: (i) x, y+1/2, z1/2.
 

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