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The asymmetric unit of the title compound, C23H23ClN4OS, contains two crystallographically independent mol­ecules in which the orientations of the propyl­amine group and chloro­phenyl rings with respect to the fused ring system are different. The terminal cyclo­hexene ring adopts a half-chair conformation. The crystal packing is stabilized by N—H...O, N—H...N and C—H...O hydrogen bonds and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027595/ci6618sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027595/ci6618Isup2.hkl
Contains datablock I

CCDC reference: 278140

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.052
  • wR factor = 0.156
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Many pyridopyrimidines exhibit pharmaceutical and germicidal activities (Anderson & Broom, 1977). Over two hundred tetrahydro- and octahydropyrido[4,3-d]pyrimidines have been synthesized as potential diuretic, antirheumatic and bacteriostatic drugs, but only a few of fully aromatic pyrido[4,3-d]pyrimidines are known. An important synthetic route of pyrido[4,3-d]pyrimidine is the condensation reaction of 4-aminonicotinic acid and amines (Ismail & Wibberley, 1967). However, this method often requires long reaction times. Recently, we have developed a new and facile regioselective annulation process, which proceeded smoothly under mild conditions via a tandem aza-Wittig and cyclization reaction, to synthesize novel pyridopyrimidine derivatives (Zhou et al., 2005). In this paper, we report the structure of the title compound, (I).

The asymmetric unit contains two crystallographically independent molecules in which the orientations of the propylamine group and chlorophenyl rings with respect to the fused ring system are different (Fig. 1). The bond lengths and angles in the thieno[2,3-b]pyridine ring system (Table 1) are in agreement with the corresponding values observed in a similar compound (Patel et al., 2003). The C—S bond lengths are longer than the values observed in both free thiophene (1.714 Å; Bonham,Momany, 1963), measured using electron diffraction, and thieno[2,3-c]pyridine [1.728 (1) and 1.731 (1) Å; Nerenz et al., 1997]. The C7—S1—C14 angle is narrower than that observed in free thiophene [92.2 (2)°]. The C5—N4—C7 angles are smaller than 120° (Ghosh & Simonsen, 1993). The CN bond lengths (Table 1) are longer than the typical CN distance of 1.28 Å (Zhao et al., 2005). In both independent molecules, the central aromatic ring system consisting of thiophene, pyridine and pyrimidine rings is essentially planar, and the terminal cyclohexene ring adopts a half-chair conformation. The crystal packing is stabilized by N—H···O, N—H···N and C—H···O hydrogen bonds (Table 2). The C15'—C20' ring and the N4/C3—C5/C7—C8 ring of the inversion related molecule at (1 − x, 1 − y, 1 − z) are stacked with a centroid–centroid distance of 3.754 (1) Å, indicating a weak ππ stacking interaction.

Experimental top

6-Methyl-4-amino-5-ethoxycarbonyltetrahydrobenzo[4,5]thieno[3,2;5,6]pyridine was prepared according to the literature procedure (Veronese et al., 1995) in 64% yield. Iminophosphorane was also synthesized according to a literature method (Wamhoff et al., 1993) in 93% yield. To a solution of iminophosphorane (0.525 g, 1 mmol) in anhydrous CH2Cl2 (10 ml) was added aromatic isocyanate (1.1 mmol) under N2 atmosphere at room temperature. The reaction mixture was left unstirred for 5 h, and then the solvent was removed under reduced pressure and Et2O/petroleum ether was added to precipitate triphenylphosphine oxide. Removal of the solvent gave carbodiimide, which was used directly without further purification. To the solution of carbodiimide prepared above in CH2Cl2 (10 ml) was added n-propylamine (1.1 mmol). The reaction mixture was stirred for 30 min, and then the solvent was removed and anhydrous ethanol (10 ml) with several drops of CH3CH2ONa in CH3CH2OH was added. The mixture was stirred for 11 h at room temperature, the solution was condensed and the residue was recrystallized from CH3CH2OH to give the title compound. Single crystals were obtained by evaporation of methanol solution (m.p. 501–503 K). Analysis calculated for C23H23ClN4OS: C 62.93, H 5.28, N 12.76%; found: C 63.26, H 5.23, N 12.45%. 1H NMR (CDCl3, TMS, 400 MHz): δ 0.91 (t, J = 7.2 Hz, 3H, CH3), 1.62 (q, J = 7.2 Hz, 2H, CH2), 1.92 (s, 4H, 2CH2), 2.87 (s, 2H, CH2), 2.94 (s, 3H, CH3 of pyridyl), 3.29 (s, 2H, CH2), 3.44 (m, 2H, NCH2), 4.41 (s, 1H, NH), 7.27–7.60 (m, 4H, Ar—H). MS (EI, m/z, %): 439 (M++1 35.14), 438 (100), 398 (14.08), 396 (17.21), 395 (24.23), 110 (15.44).

Refinement top

In one of the independent molecules, the propylamine group is disordered over two orientations with occupancies of 0.515 (8) and 0.485 (8). The disorder was modelled with C—C and C···C distances of 1.54 and 2.51 Å, respectively. All the H atoms were placed in idealized positions and constrained to ride on their parent atoms, with N—H = 0.86 and 0.90 Å, C—H = 0.93–0.97 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N) for other H atoms.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids. Both components of the disordered propylamine group are shown.
3-(4-Chlorophenyl)-5-methyl-2-propylamino-8,9,10,11-tetrahydro- 2-benzothieno[2'3';2,3]pyrido[4,5-d]pyrimidin-4(3H)-one top
Crystal data top
C23H23ClN4OSZ = 4
Mr = 438.96F(000) = 920
Triclinic, P1Dx = 1.344 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.8884 (6) ÅCell parameters from 3870 reflections
b = 13.3784 (7) Åθ = 2.3–26.9°
c = 15.7892 (8) ŵ = 0.30 mm1
α = 114.054 (1)°T = 292 K
β = 98.926 (1)°Block, colourless
γ = 101.335 (1)°0.40 × 0.30 × 0.30 mm
V = 2169.42 (19) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
9849 independent reflections
Radiation source: fine-focus sealed tube6468 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ϕ and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.891, Tmax = 0.917k = 1717
25134 measured reflectionsl = 2020
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) = 0.156H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0778P)2 + 0.1323P]
where P = (Fo2 + 2Fc2)/3
9849 reflections(Δ/σ)max = 0.001
574 parametersΔρmax = 0.32 e Å3
7 restraintsΔρmin = 0.21 e Å3
Crystal data top
C23H23ClN4OSγ = 101.335 (1)°
Mr = 438.96V = 2169.42 (19) Å3
Triclinic, P1Z = 4
a = 11.8884 (6) ÅMo Kα radiation
b = 13.3784 (7) ŵ = 0.30 mm1
c = 15.7892 (8) ÅT = 292 K
α = 114.054 (1)°0.40 × 0.30 × 0.30 mm
β = 98.926 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
9849 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6468 reflections with I > 2σ(I)
Tmin = 0.891, Tmax = 0.917Rint = 0.040
25134 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0537 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 1.03Δρmax = 0.32 e Å3
9849 reflectionsΔρmin = 0.21 e Å3
574 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)
S10.83965 (7)0.78315 (6)0.38004 (4)0.0676 (2)
Cl10.69608 (9)0.01047 (6)0.43385 (5)0.0987 (3)
O10.75577 (16)0.26620 (13)0.01717 (11)0.0590 (4)
N10.77021 (15)0.38157 (14)0.05490 (12)0.0424 (4)
N20.81663 (15)0.58305 (14)0.03154 (12)0.0431 (4)
N30.79331 (16)0.49906 (15)0.13039 (12)0.0482 (4)
H30.77500.43780.18380.058*
N40.79378 (17)0.55450 (16)0.28406 (13)0.0506 (5)
C10.79393 (17)0.49006 (17)0.04908 (14)0.0404 (5)
C20.76997 (18)0.36276 (18)0.02714 (15)0.0427 (5)
C30.78741 (17)0.46588 (17)0.11601 (14)0.0411 (5)
C40.81125 (17)0.57168 (17)0.11311 (14)0.0396 (5)
C50.78045 (18)0.46055 (18)0.20347 (15)0.0448 (5)
C60.7560 (2)0.3517 (2)0.21206 (17)0.0582 (6)
H6A0.74390.36650.27430.087*
H6B0.82250.32120.20430.087*
H6C0.68600.29760.16320.087*
C70.81831 (19)0.65471 (19)0.27952 (15)0.0486 (5)
C80.82894 (18)0.67145 (18)0.19942 (14)0.0432 (5)
C90.85478 (18)0.79069 (18)0.22070 (15)0.0461 (5)
C100.8729 (2)0.84047 (19)0.15200 (17)0.0527 (6)
H10A0.80990.79670.09290.063*
H10B0.94790.83450.13640.063*
C110.8735 (3)0.9652 (2)0.1946 (2)0.0797 (8)
H11A0.90881.00000.15810.096*
H11B0.79200.96850.18760.096*
C120.9395 (3)1.0330 (2)0.2976 (2)0.0866 (9)
H12A0.93611.11120.31930.104*
H12B1.02231.03430.30420.104*
C130.8916 (3)0.9870 (2)0.3606 (2)0.0767 (8)
H13A0.82011.00880.37200.092*
H13B0.94971.01930.42220.092*
C140.8632 (2)0.8585 (2)0.31397 (17)0.0581 (6)
C150.75202 (19)0.28309 (17)0.14585 (14)0.0442 (5)
C160.6392 (2)0.21056 (19)0.19575 (16)0.0525 (6)
H160.57510.22290.17000.063*
C170.6219 (2)0.1191 (2)0.28468 (17)0.0616 (7)
H170.54620.06970.31920.074*
C180.7177 (3)0.10216 (19)0.32121 (16)0.0588 (6)
C190.8304 (2)0.1727 (2)0.27115 (17)0.0584 (6)
H190.89460.15960.29660.070*
C200.8474 (2)0.2634 (2)0.18246 (16)0.0520 (6)
H200.92370.31120.14740.062*
C210.82263 (19)0.60916 (19)0.13101 (16)0.0483 (5)
H21A0.78960.66040.08500.058*
H21B0.78610.59970.19420.058*
C220.9532 (2)0.6620 (2)0.1070 (2)0.0648 (7)
H22A0.98590.61220.15440.078*
H22B0.99030.66910.04480.078*
C230.9826 (3)0.7784 (3)0.1044 (3)0.1018 (11)
H23A1.06730.81140.08440.153*
H23B0.94720.82700.05980.153*
H23C0.95210.77100.16730.153*
S1'0.59009 (6)0.06546 (6)0.18901 (4)0.06011 (19)
Cl1'0.53506 (6)0.69778 (7)1.00401 (4)0.0787 (2)
O1'0.68877 (14)0.37945 (15)0.66260 (10)0.0613 (4)
N1'0.50461 (15)0.38250 (15)0.60285 (11)0.0429 (4)
N2'0.40559 (15)0.28553 (15)0.43701 (12)0.0452 (4)
N3'0.31617 (16)0.39209 (18)0.54449 (13)0.0595 (5)
H3'A0.32760.44860.59990.071*0.515 (8)
H3'B0.31380.43400.60520.071*0.485 (8)
N4'0.70662 (17)0.17901 (16)0.37671 (13)0.0516 (5)
C1'0.40820 (19)0.35119 (18)0.52575 (14)0.0435 (5)
C2'0.60838 (19)0.34809 (18)0.59099 (14)0.0445 (5)
C3'0.60749 (18)0.27802 (17)0.49249 (14)0.0409 (5)
C4'0.50282 (18)0.24763 (17)0.42087 (14)0.0406 (5)
C5'0.70776 (19)0.24138 (19)0.46733 (15)0.0468 (5)
C6'0.8233 (2)0.2721 (2)0.53933 (17)0.0619 (6)
H6'A0.87880.24040.50650.093*
H6'B0.80980.24180.58370.093*
H6'C0.85500.35380.57380.093*
C7'0.6044 (2)0.14785 (18)0.31009 (15)0.0471 (5)
C8'0.49967 (19)0.17450 (17)0.32520 (14)0.0431 (5)
C9'0.4048 (2)0.12283 (17)0.23743 (14)0.0448 (5)
C10'0.2773 (2)0.1222 (2)0.22841 (16)0.0548 (6)
H10C0.26950.19550.23450.066*
H10D0.25100.11020.27960.066*
C11'0.1996 (2)0.0268 (2)0.13060 (17)0.0656 (7)
H11C0.19440.04690.12970.079*
H11D0.11990.03480.12080.079*
C12'0.2512 (3)0.0324 (2)0.05077 (17)0.0712 (8)
H12C0.26130.10800.05450.085*
H12D0.19660.02260.01080.085*
C13'0.3702 (3)0.0071 (2)0.05733 (16)0.0660 (7)
H13C0.35760.07470.03170.079*
H13D0.41260.03350.01910.079*
C14'0.4433 (2)0.06570 (18)0.16013 (15)0.0519 (6)
C15'0.50559 (18)0.45880 (18)0.69984 (14)0.0411 (5)
C16'0.4849 (2)0.4146 (2)0.76316 (15)0.0491 (5)
H16A0.46550.33610.74260.059*
C17'0.4934 (2)0.4883 (2)0.85735 (16)0.0537 (6)
H17A0.48090.46020.90120.064*
C18'0.52042 (19)0.6032 (2)0.88507 (15)0.0490 (5)
C19'0.53746 (19)0.64733 (19)0.82174 (16)0.0505 (5)
H19A0.55320.72550.84170.061*
C20'0.53092 (19)0.57393 (19)0.72802 (15)0.0468 (5)
H20A0.54360.60240.68440.056*
C21'0.1968 (5)0.3482 (7)0.4780 (5)0.053 (2)0.515 (8)
H21C0.13610.34970.51260.063*0.515 (8)
H21D0.18360.27030.43000.063*0.515 (8)
C22'0.1936 (6)0.4259 (5)0.4315 (5)0.075 (2)0.515 (8)
H22C0.25070.41930.39320.090*0.515 (8)
H22D0.21530.50450.48070.090*0.515 (8)
C23'0.0679 (8)0.3939 (10)0.3669 (6)0.093 (3)0.515 (8)
H23D0.07210.42320.32090.140*0.515 (8)
H23E0.01760.42630.40590.140*0.515 (8)
H23F0.03570.31220.33390.140*0.515 (8)
C21A0.2202 (6)0.3681 (10)0.4607 (5)0.066 (3)0.485 (8)
H21E0.17560.28790.43070.079*0.485 (8)
H21F0.25570.38250.41390.079*0.485 (8)
C22A0.1364 (6)0.4392 (6)0.4871 (5)0.082 (3)0.485 (8)
H22E0.17840.51870.50820.098*0.485 (8)
H22F0.10960.43350.54040.098*0.485 (8)
C23A0.0286 (8)0.4018 (11)0.4032 (6)0.093 (3)0.485 (8)
H23G0.01170.46800.40090.139*0.485 (8)
H23H0.03880.35770.41180.139*0.485 (8)
H23I0.04520.35600.34420.139*0.485 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0945 (5)0.0549 (4)0.0385 (3)0.0194 (3)0.0211 (3)0.0066 (3)
Cl10.1573 (8)0.0568 (4)0.0531 (4)0.0172 (5)0.0377 (5)0.0000 (3)
O10.0837 (12)0.0400 (9)0.0488 (9)0.0175 (8)0.0143 (8)0.0172 (7)
N10.0470 (10)0.0381 (9)0.0340 (9)0.0107 (8)0.0098 (7)0.0098 (7)
N20.0474 (10)0.0399 (9)0.0347 (9)0.0103 (8)0.0089 (8)0.0116 (7)
N30.0598 (11)0.0413 (10)0.0331 (9)0.0102 (8)0.0091 (8)0.0100 (8)
N40.0592 (12)0.0526 (11)0.0372 (10)0.0166 (9)0.0153 (8)0.0165 (8)
C10.0373 (11)0.0427 (12)0.0363 (11)0.0115 (9)0.0086 (8)0.0137 (9)
C20.0414 (11)0.0436 (12)0.0380 (11)0.0117 (9)0.0089 (9)0.0144 (9)
C30.0386 (11)0.0420 (11)0.0376 (11)0.0122 (9)0.0086 (9)0.0133 (9)
C40.0344 (10)0.0441 (11)0.0350 (10)0.0119 (9)0.0094 (8)0.0126 (9)
C50.0431 (12)0.0494 (13)0.0413 (12)0.0144 (10)0.0122 (9)0.0190 (10)
C60.0693 (16)0.0588 (15)0.0528 (14)0.0196 (12)0.0182 (12)0.0301 (12)
C70.0499 (13)0.0481 (13)0.0392 (12)0.0152 (10)0.0128 (10)0.0109 (10)
C80.0386 (11)0.0455 (12)0.0377 (11)0.0125 (9)0.0084 (9)0.0120 (9)
C90.0423 (12)0.0433 (12)0.0431 (12)0.0138 (9)0.0089 (9)0.0106 (9)
C100.0568 (14)0.0456 (13)0.0502 (13)0.0163 (11)0.0105 (11)0.0170 (11)
C110.107 (2)0.0544 (16)0.075 (2)0.0286 (16)0.0181 (17)0.0260 (15)
C120.116 (3)0.0425 (15)0.080 (2)0.0169 (16)0.0170 (19)0.0136 (15)
C130.103 (2)0.0465 (14)0.0584 (16)0.0235 (14)0.0149 (15)0.0041 (12)
C140.0661 (15)0.0491 (13)0.0463 (13)0.0180 (11)0.0136 (11)0.0093 (11)
C150.0534 (13)0.0387 (11)0.0349 (11)0.0149 (10)0.0108 (9)0.0110 (9)
C160.0538 (14)0.0472 (13)0.0462 (13)0.0101 (11)0.0142 (11)0.0131 (10)
C170.0723 (17)0.0462 (13)0.0443 (13)0.0017 (12)0.0076 (12)0.0093 (11)
C180.0904 (19)0.0419 (13)0.0379 (12)0.0188 (13)0.0186 (13)0.0116 (10)
C190.0725 (17)0.0579 (15)0.0522 (14)0.0322 (13)0.0271 (13)0.0222 (12)
C200.0504 (13)0.0530 (13)0.0457 (12)0.0187 (11)0.0110 (10)0.0148 (11)
C210.0514 (13)0.0503 (13)0.0422 (12)0.0170 (10)0.0092 (10)0.0201 (10)
C220.0522 (14)0.0619 (16)0.0768 (18)0.0148 (12)0.0137 (13)0.0299 (14)
C230.086 (2)0.0644 (19)0.151 (3)0.0082 (16)0.033 (2)0.050 (2)
S1'0.0759 (4)0.0615 (4)0.0376 (3)0.0271 (3)0.0212 (3)0.0118 (3)
Cl1'0.0739 (4)0.0941 (5)0.0372 (3)0.0200 (4)0.0176 (3)0.0013 (3)
O1'0.0541 (9)0.0815 (12)0.0332 (8)0.0281 (8)0.0026 (7)0.0110 (8)
N1'0.0465 (10)0.0477 (10)0.0294 (8)0.0150 (8)0.0089 (7)0.0125 (7)
N2'0.0462 (10)0.0506 (10)0.0317 (9)0.0168 (8)0.0073 (7)0.0118 (8)
N3'0.0486 (11)0.0744 (14)0.0386 (10)0.0275 (10)0.0073 (9)0.0069 (9)
N4'0.0576 (12)0.0552 (11)0.0408 (10)0.0227 (9)0.0157 (9)0.0166 (9)
C1'0.0465 (12)0.0459 (12)0.0338 (11)0.0135 (10)0.0076 (9)0.0147 (9)
C2'0.0489 (12)0.0456 (12)0.0349 (11)0.0157 (10)0.0090 (10)0.0139 (9)
C3'0.0468 (12)0.0418 (11)0.0321 (10)0.0140 (9)0.0086 (9)0.0149 (9)
C4'0.0479 (12)0.0393 (11)0.0334 (10)0.0116 (9)0.0105 (9)0.0156 (9)
C5'0.0515 (13)0.0490 (12)0.0413 (12)0.0186 (10)0.0122 (10)0.0200 (10)
C6'0.0545 (14)0.0763 (17)0.0527 (14)0.0294 (13)0.0107 (11)0.0236 (13)
C7'0.0599 (14)0.0444 (12)0.0375 (11)0.0185 (10)0.0170 (10)0.0158 (9)
C8'0.0556 (13)0.0383 (11)0.0329 (10)0.0126 (10)0.0123 (9)0.0139 (9)
C9'0.0594 (14)0.0381 (11)0.0308 (10)0.0129 (10)0.0094 (9)0.0112 (9)
C10'0.0577 (14)0.0562 (14)0.0388 (12)0.0109 (11)0.0051 (10)0.0158 (11)
C11'0.0641 (16)0.0611 (15)0.0478 (14)0.0001 (12)0.0009 (12)0.0158 (12)
C12'0.0810 (19)0.0653 (16)0.0374 (13)0.0068 (14)0.0068 (12)0.0153 (12)
C13'0.0863 (19)0.0564 (15)0.0351 (12)0.0093 (13)0.0094 (12)0.0089 (11)
C14'0.0714 (15)0.0423 (12)0.0345 (11)0.0131 (11)0.0134 (10)0.0118 (9)
C15'0.0430 (11)0.0460 (12)0.0292 (10)0.0144 (9)0.0086 (8)0.0118 (9)
C16'0.0566 (13)0.0495 (13)0.0416 (12)0.0176 (11)0.0130 (10)0.0199 (10)
C17'0.0574 (14)0.0721 (17)0.0358 (12)0.0207 (12)0.0160 (10)0.0263 (11)
C18'0.0417 (12)0.0603 (15)0.0338 (11)0.0145 (10)0.0103 (9)0.0106 (10)
C19'0.0477 (13)0.0440 (12)0.0465 (13)0.0094 (10)0.0118 (10)0.0100 (10)
C20'0.0517 (13)0.0496 (13)0.0380 (11)0.0130 (10)0.0127 (10)0.0192 (10)
C21'0.055 (4)0.056 (3)0.039 (3)0.012 (3)0.022 (3)0.012 (3)
C22'0.087 (5)0.073 (4)0.065 (4)0.024 (3)0.007 (3)0.034 (3)
C23'0.092 (6)0.111 (6)0.069 (5)0.024 (5)0.010 (4)0.047 (5)
C21A0.043 (4)0.109 (8)0.045 (4)0.039 (4)0.015 (3)0.024 (4)
C22A0.073 (4)0.100 (5)0.059 (4)0.041 (4)0.002 (3)0.023 (3)
C23A0.077 (5)0.134 (8)0.077 (6)0.041 (5)0.002 (4)0.059 (6)
Geometric parameters (Å, º) top
S1—C71.737 (2)N1'—C15'1.450 (2)
S1—C141.738 (3)N2'—C1'1.307 (2)
Cl1—C181.738 (2)N2'—C4'1.369 (3)
O1—C21.209 (2)N3'—C1'1.337 (3)
N1—C11.384 (3)N3'—C21'1.473 (6)
N1—C21.417 (3)N3'—C21A1.483 (6)
N1—C151.447 (2)N3'—H3'A0.86
N2—C11.308 (2)N3'—H3'B0.90
N2—C41.367 (3)N4'—C5'1.327 (3)
N3—C11.337 (3)N4'—C7'1.343 (3)
N3—C211.450 (3)C2'—C3'1.449 (3)
N3—H30.86C3'—C4'1.408 (3)
N4—C51.334 (3)C3'—C5'1.427 (3)
N4—C71.349 (3)C4'—C8'1.415 (3)
C2—C31.461 (3)C5'—C6'1.503 (3)
C3—C41.409 (3)C6'—H6'A0.96
C3—C51.426 (3)C6'—H6'B0.96
C4—C81.414 (3)C6'—H6'C0.96
C5—C61.493 (3)C7'—C8'1.390 (3)
C6—H6A0.96C8'—C9'1.448 (3)
C6—H6B0.96C9'—C14'1.353 (3)
C6—H6C0.96C9'—C10'1.498 (3)
C7—C81.391 (3)C10'—C11'1.535 (3)
C8—C91.446 (3)C10'—H10C0.97
C9—C141.353 (3)C10'—H10D0.97
C9—C101.507 (3)C11'—C12'1.507 (4)
C10—C111.522 (3)C11'—H11C0.97
C10—H10A0.97C11'—H11D0.97
C10—H10B0.97C12'—C13'1.515 (4)
C11—C121.486 (4)C12'—H12C0.97
C11—H11A0.97C12'—H12D0.97
C11—H11B0.97C13'—C14'1.504 (3)
C12—C131.494 (4)C13'—H13C0.97
C12—H12A0.97C13'—H13D0.97
C12—H12B0.97C15'—C20'1.371 (3)
C13—C141.508 (3)C15'—C16'1.382 (3)
C13—H13A0.97C16'—C17'1.383 (3)
C13—H13B0.97C16'—H16A0.93
C15—C201.374 (3)C17'—C18'1.368 (3)
C15—C161.378 (3)C17'—H17A0.93
C16—C171.387 (3)C18'—C19'1.373 (3)
C16—H160.93C19'—C20'1.382 (3)
C17—C181.371 (4)C19'—H19A0.93
C17—H170.93C20'—H20A0.93
C18—C191.370 (4)C21'—C22'1.499 (7)
C19—C201.380 (3)C21'—H21C0.97
C19—H190.93C21'—H21D0.97
C20—H200.93C22'—C23'1.541 (7)
C21—C221.490 (3)C22'—H22C0.97
C21—H21A0.97C22'—H22D0.97
C21—H21B0.97C23'—H23D0.96
C22—C231.510 (4)C23'—H23E0.96
C22—H22A0.97C23'—H23F0.96
C22—H22B0.97C21A—C22A1.500 (8)
C23—H23A0.96C21A—H21E0.97
C23—H23B0.96C21A—H21F0.97
C23—H23C0.96C22A—C23A1.525 (7)
S1'—C7'1.734 (2)C22A—H22E0.97
S1'—C14'1.735 (3)C22A—H22F0.97
Cl1'—C18'1.741 (2)C23A—H23G0.96
O1'—C2'1.220 (2)C23A—H23H0.96
N1'—C1'1.391 (3)C23A—H23I0.96
N1'—C2'1.412 (3)
C7—S1—C1491.00 (11)C21A—N3'—H3'A121.9
C1—N1—C2122.21 (17)C1'—N3'—H3'B121.4
C1—N1—C15120.14 (16)C21'—N3'—H3'B110.6
C2—N1—C15117.55 (16)C21A—N3'—H3'B121.7
C1—N2—C4118.07 (18)C5'—N4'—C7'116.56 (18)
C1—N3—C21121.83 (17)N2'—C1'—N3'119.66 (18)
C1—N3—H3119.1N2'—C1'—N1'122.58 (19)
C21—N3—H3119.1N3'—C1'—N1'117.75 (18)
C5—N4—C7116.82 (18)O1'—C2'—N1'118.21 (18)
N2—C1—N3118.99 (19)O1'—C2'—C3'126.62 (19)
N2—C1—N1123.28 (18)N1'—C2'—C3'115.17 (17)
N3—C1—N1117.74 (17)C4'—C3'—C5'120.47 (18)
O1—C2—N1118.30 (18)C4'—C3'—C2'117.15 (18)
O1—C2—C3127.29 (19)C5'—C3'—C2'122.38 (18)
N1—C2—C3114.41 (18)N2'—C4'—C3'124.73 (18)
C4—C3—C5120.52 (18)N2'—C4'—C8'118.07 (18)
C4—C3—C2118.07 (18)C3'—C4'—C8'117.19 (19)
C5—C3—C2121.41 (19)N4'—C5'—C3'121.82 (19)
N2—C4—C3123.73 (18)N4'—C5'—C6'114.54 (19)
N2—C4—C8118.32 (18)C3'—C5'—C6'123.62 (19)
C3—C4—C8117.95 (18)C5'—C6'—H6'A109.5
N4—C5—C3121.34 (19)C5'—C6'—H6'B109.5
N4—C5—C6115.15 (19)H6'A—C6'—H6'B109.5
C3—C5—C6123.50 (19)C5'—C6'—H6'C109.5
C5—C6—H6A109.5H6'A—C6'—H6'C109.5
C5—C6—H6B109.5H6'B—C6'—H6'C109.5
H6A—C6—H6B109.5N4'—C7'—C8'127.31 (19)
C5—C6—H6C109.5N4'—C7'—S1'121.46 (16)
H6A—C6—H6C109.5C8'—C7'—S1'111.23 (16)
H6B—C6—H6C109.5C7'—C8'—C4'116.41 (19)
N4—C7—C8127.34 (19)C7'—C8'—C9'112.77 (18)
N4—C7—S1121.17 (17)C4'—C8'—C9'130.8 (2)
C8—C7—S1111.49 (17)C14'—C9'—C8'111.1 (2)
C7—C8—C4115.99 (19)C14'—C9'—C10'121.7 (2)
C7—C8—C9112.30 (19)C8'—C9'—C10'127.08 (18)
C4—C8—C9131.7 (2)C9'—C10'—C11'110.02 (19)
C14—C9—C8111.9 (2)C9'—C10'—H10C109.7
C14—C9—C10121.1 (2)C11'—C10'—H10C109.7
C8—C9—C10126.98 (19)C9'—C10'—H10D109.7
C9—C10—C11111.6 (2)C11'—C10'—H10D109.7
C9—C10—H10A109.3H10C—C10'—H10D108.2
C11—C10—H10A109.3C12'—C11'—C10'110.5 (2)
C9—C10—H10B109.3C12'—C11'—H11C109.6
C11—C10—H10B109.3C10'—C11'—H11C109.6
H10A—C10—H10B108.0C12'—C11'—H11D109.6
C12—C11—C10113.9 (2)C10'—C11'—H11D109.6
C12—C11—H11A108.8H11C—C11'—H11D108.1
C10—C11—H11A108.8C11'—C12'—C13'111.1 (2)
C12—C11—H11B108.8C11'—C12'—H12C109.4
C10—C11—H11B108.8C13'—C12'—H12C109.4
H11A—C11—H11B107.7C11'—C12'—H12D109.4
C11—C12—C13113.2 (3)C13'—C12'—H12D109.4
C11—C12—H12A108.9H12C—C12'—H12D108.0
C13—C12—H12A108.9C14'—C13'—C12'110.3 (2)
C11—C12—H12B108.9C14'—C13'—H13C109.6
C13—C12—H12B108.9C12'—C13'—H13C109.6
H12A—C12—H12B107.8C14'—C13'—H13D109.6
C12—C13—C14110.4 (2)C12'—C13'—H13D109.6
C12—C13—H13A109.6H13C—C13'—H13D108.1
C14—C13—H13A109.6C9'—C14'—C13'125.4 (2)
C12—C13—H13B109.6C9'—C14'—S1'113.70 (17)
C14—C13—H13B109.6C13'—C14'—S1'120.92 (18)
H13A—C13—H13B108.1C20'—C15'—C16'121.16 (19)
C9—C14—C13125.7 (2)C20'—C15'—N1'119.35 (18)
C9—C14—S1113.33 (18)C16'—C15'—N1'119.45 (18)
C13—C14—S1120.97 (19)C15'—C16'—C17'119.3 (2)
C20—C15—C16120.4 (2)C15'—C16'—H16A120.3
C20—C15—N1119.65 (19)C17'—C16'—H16A120.3
C16—C15—N1119.94 (19)C18'—C17'—C16'119.0 (2)
C15—C16—C17119.6 (2)C18'—C17'—H17A120.5
C15—C16—H16120.2C16'—C17'—H17A120.5
C17—C16—H16120.2C17'—C18'—C19'121.9 (2)
C18—C17—C16119.3 (2)C17'—C18'—Cl1'119.74 (18)
C18—C17—H17120.4C19'—C18'—Cl1'118.33 (18)
C16—C17—H17120.4C18'—C19'—C20'119.1 (2)
C19—C18—C17121.4 (2)C18'—C19'—H19A120.5
C19—C18—Cl1119.1 (2)C20'—C19'—H19A120.5
C17—C18—Cl1119.5 (2)C15'—C20'—C19'119.4 (2)
C18—C19—C20119.1 (2)C15'—C20'—H20A120.3
C18—C19—H19120.4C19'—C20'—H20A120.3
C20—C19—H19120.4N3'—C21'—C22'105.8 (5)
C15—C20—C19120.1 (2)N3'—C21'—H21C110.6
C15—C20—H20119.9C22'—C21'—H21C110.6
C19—C20—H20119.9N3'—C21'—H21D110.6
N3—C21—C22112.82 (19)C22'—C21'—H21D110.6
N3—C21—H21A109.0H21C—C21'—H21D108.7
C22—C21—H21A109.0C21'—C22'—C23'110.0 (5)
N3—C21—H21B109.0C21'—C22'—H22C109.7
C22—C21—H21B109.0C23'—C22'—H22C109.7
H21A—C21—H21B107.8C21'—C22'—H22D109.7
C21—C22—C23112.3 (2)C23'—C22'—H22D109.7
C21—C22—H22A109.1H22C—C22'—H22D108.2
C23—C22—H22A109.1N3'—C21A—C22A112.9 (6)
C21—C22—H22B109.1N3'—C21A—H21E109.0
C23—C22—H22B109.1C22A—C21A—H21E109.0
H22A—C22—H22B107.9N3'—C21A—H21F109.0
C22—C23—H23A109.5C22A—C21A—H21F109.0
C22—C23—H23B109.5H21E—C21A—H21F107.8
H23A—C23—H23B109.5C21A—C22A—C23A112.2 (6)
C22—C23—H23C109.5C21A—C22A—H22E109.2
H23A—C23—H23C109.5C23A—C22A—H22E109.2
H23B—C23—H23C109.5C21A—C22A—H22F109.2
C7'—S1'—C14'91.06 (10)C23A—C22A—H22F109.2
C1'—N1'—C2'122.54 (17)H22E—C22A—H22F107.9
C1'—N1'—C15'120.77 (17)C22A—C23A—H23G109.5
C2'—N1'—C15'116.59 (16)C22A—C23A—H23H109.5
C1'—N2'—C4'117.71 (17)H23G—C23A—H23H109.5
C1'—N3'—C21'125.3 (4)C22A—C23A—H23I109.5
C1'—N3'—C21A116.9 (3)H23G—C23A—H23I109.5
C1'—N3'—H3'A117.3H23H—C23A—H23I109.5
C21'—N3'—H3'A117.3
C4—N2—C1—N3176.93 (18)C21A—N3'—C1'—N2'5.5 (6)
C4—N2—C1—N13.1 (3)C21'—N3'—C1'—N1'164.6 (4)
C21—N3—C1—N23.0 (3)C21A—N3'—C1'—N1'173.6 (6)
C21—N3—C1—N1177.02 (17)C2'—N1'—C1'—N2'1.6 (3)
C2—N1—C1—N20.7 (3)C15'—N1'—C1'—N2'177.81 (19)
C15—N1—C1—N2176.76 (18)C2'—N1'—C1'—N3'177.4 (2)
C2—N1—C1—N3179.31 (18)C15'—N1'—C1'—N3'1.2 (3)
C15—N1—C1—N33.3 (3)C1'—N1'—C2'—O1'180.0 (2)
C1—N1—C2—O1175.47 (18)C15'—N1'—C2'—O1'3.7 (3)
C15—N1—C2—O10.7 (3)C1'—N1'—C2'—C3'0.2 (3)
C1—N1—C2—C34.6 (3)C15'—N1'—C2'—C3'176.12 (17)
C15—N1—C2—C3179.30 (16)O1'—C2'—C3'—C4'177.3 (2)
O1—C2—C3—C4175.3 (2)N1'—C2'—C3'—C4'3.0 (3)
N1—C2—C3—C44.7 (3)O1'—C2'—C3'—C5'3.4 (4)
O1—C2—C3—C54.8 (3)N1'—C2'—C3'—C5'176.36 (19)
N1—C2—C3—C5175.16 (18)C1'—N2'—C4'—C3'2.7 (3)
C1—N2—C4—C32.7 (3)C1'—N2'—C4'—C8'178.67 (19)
C1—N2—C4—C8176.41 (17)C5'—C3'—C4'—N2'174.88 (19)
C5—C3—C4—N2178.51 (18)C2'—C3'—C4'—N2'4.5 (3)
C2—C3—C4—N21.4 (3)C5'—C3'—C4'—C8'3.7 (3)
C5—C3—C4—C80.6 (3)C2'—C3'—C4'—C8'176.92 (18)
C2—C3—C4—C8179.56 (17)C7'—N4'—C5'—C3'2.8 (3)
C7—N4—C5—C32.3 (3)C7'—N4'—C5'—C6'178.8 (2)
C7—N4—C5—C6178.72 (19)C4'—C3'—C5'—N4'0.6 (3)
C4—C3—C5—N41.4 (3)C2'—C3'—C5'—N4'178.7 (2)
C2—C3—C5—N4178.49 (19)C4'—C3'—C5'—C6'178.8 (2)
C4—C3—C5—C6179.8 (2)C2'—C3'—C5'—C6'0.5 (3)
C2—C3—C5—C60.4 (3)C5'—N4'—C7'—C8'0.7 (3)
C5—N4—C7—C81.5 (3)C5'—N4'—C7'—S1'179.56 (17)
C5—N4—C7—S1179.10 (16)C14'—S1'—C7'—N4'179.32 (19)
C14—S1—C7—N4179.7 (2)C14'—S1'—C7'—C8'0.88 (18)
C14—S1—C7—C80.19 (18)N4'—C7'—C8'—C4'3.6 (3)
N4—C7—C8—C40.4 (3)S1'—C7'—C8'—C4'176.18 (15)
S1—C7—C8—C4179.06 (14)N4'—C7'—C8'—C9'177.6 (2)
N4—C7—C8—C9179.4 (2)S1'—C7'—C8'—C9'2.6 (2)
S1—C7—C8—C90.0 (2)N2'—C4'—C8'—C7'173.20 (18)
N2—C4—C8—C7177.77 (18)C3'—C4'—C8'—C7'5.5 (3)
C3—C4—C8—C71.4 (3)N2'—C4'—C8'—C9'5.4 (3)
N2—C4—C8—C91.0 (3)C3'—C4'—C8'—C9'176.0 (2)
C3—C4—C8—C9179.8 (2)C7'—C8'—C9'—C14'3.5 (3)
C7—C8—C9—C140.3 (3)C4'—C8'—C9'—C14'175.1 (2)
C4—C8—C9—C14179.1 (2)C7'—C8'—C9'—C10'172.5 (2)
C7—C8—C9—C10179.5 (2)C4'—C8'—C9'—C10'8.9 (4)
C4—C8—C9—C101.6 (4)C14'—C9'—C10'—C11'14.9 (3)
C14—C9—C10—C1112.4 (3)C8'—C9'—C10'—C11'160.7 (2)
C8—C9—C10—C11168.5 (2)C9'—C10'—C11'—C12'49.8 (3)
C9—C10—C11—C1241.3 (3)C10'—C11'—C12'—C13'65.6 (3)
C10—C11—C12—C1358.9 (4)C11'—C12'—C13'—C14'41.8 (3)
C11—C12—C13—C1442.8 (4)C8'—C9'—C14'—C13'176.7 (2)
C8—C9—C14—C13178.7 (2)C10'—C9'—C14'—C13'7.0 (4)
C10—C9—C14—C130.6 (4)C8'—C9'—C14'—S1'2.8 (2)
C8—C9—C14—S10.4 (3)C10'—C9'—C14'—S1'173.43 (17)
C10—C9—C14—S1179.73 (17)C12'—C13'—C14'—C9'6.6 (3)
C12—C13—C14—C914.4 (4)C12'—C13'—C14'—S1'172.92 (18)
C12—C13—C14—S1164.7 (2)C7'—S1'—C14'—C9'1.19 (19)
C7—S1—C14—C90.4 (2)C7'—S1'—C14'—C13'178.4 (2)
C7—S1—C14—C13178.8 (2)C1'—N1'—C15'—C20'78.1 (3)
C1—N1—C15—C2073.4 (3)C2'—N1'—C15'—C20'98.3 (2)
C2—N1—C15—C20102.8 (2)C1'—N1'—C15'—C16'104.0 (2)
C1—N1—C15—C16105.8 (2)C2'—N1'—C15'—C16'79.5 (2)
C2—N1—C15—C1678.0 (3)C20'—C15'—C16'—C17'1.9 (3)
C20—C15—C16—C171.8 (3)N1'—C15'—C16'—C17'175.91 (19)
N1—C15—C16—C17177.4 (2)C15'—C16'—C17'—C18'0.9 (3)
C15—C16—C17—C180.3 (4)C16'—C17'—C18'—C19'1.1 (3)
C16—C17—C18—C191.0 (4)C16'—C17'—C18'—Cl1'178.44 (17)
C16—C17—C18—Cl1178.53 (18)C17'—C18'—C19'—C20'2.1 (3)
C17—C18—C19—C200.7 (4)Cl1'—C18'—C19'—C20'177.41 (16)
Cl1—C18—C19—C20178.84 (18)C16'—C15'—C20'—C19'0.9 (3)
C16—C15—C20—C192.1 (3)N1'—C15'—C20'—C19'176.94 (18)
N1—C15—C20—C19177.1 (2)C18'—C19'—C20'—C15'1.1 (3)
C18—C19—C20—C150.9 (4)C1'—N3'—C21'—C22'98.1 (7)
C1—N3—C21—C2282.8 (3)C21A—N3'—C21'—C22'26.3 (15)
N3—C21—C22—C23178.0 (2)N3'—C21'—C22'—C23'174.9 (6)
C4'—N2'—C1'—N3'178.58 (19)C1'—N3'—C21A—C22A166.4 (7)
C4'—N2'—C1'—N1'0.4 (3)C21'—N3'—C21A—C22A73.9 (16)
C21'—N3'—C1'—N2'16.4 (5)N3'—C21A—C22A—C23A171.7 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···N4i0.902.303.072 (3)144
N3—H3···O1ii0.862.222.912 (2)138
C13—H13C···O1iii0.972.383.285 (3)154
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z1; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC23H23ClN4OS
Mr438.96
Crystal system, space groupTriclinic, P1
Temperature (K)292
a, b, c (Å)11.8884 (6), 13.3784 (7), 15.7892 (8)
α, β, γ (°)114.054 (1), 98.926 (1), 101.335 (1)
V3)2169.42 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.30
Crystal size (mm)0.40 × 0.30 × 0.30
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.891, 0.917
No. of measured, independent and
observed [I > 2σ(I)] reflections
25134, 9849, 6468
Rint0.040
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.156, 1.03
No. of reflections9849
No. of parameters574
No. of restraints7
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Selected geometric parameters (Å, º) top
S1—C71.737 (2)S1'—C7'1.734 (2)
S1—C141.738 (3)S1'—C14'1.735 (3)
O1—C21.209 (2)O1'—C2'1.220 (2)
N2—C11.308 (2)N2'—C1'1.307 (2)
N2—C41.367 (3)N2'—C4'1.369 (3)
N4—C51.334 (3)N4'—C5'1.327 (3)
N4—C71.349 (3)N4'—C7'1.343 (3)
C7—S1—C1491.00 (11)C7'—S1'—C14'91.06 (10)
C1—N2—C4118.07 (18)C1'—N2'—C4'117.71 (17)
C5—N4—C7116.82 (18)C5'—N4'—C7'116.56 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3'—H3'B···N4i0.902.303.072 (3)144
N3—H3···O1'ii0.862.222.912 (2)138
C13'—H13C···O1iii0.972.383.285 (3)154
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z1; (iii) x+1, y, z.
 

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