3-(4-Chloro­phen­yl)-2-(2,4-dichloro­phen­oxy)-5-methyl-8,9,10,11-tetra­hydro-2-benzothieno[2′,3′:2,3]pyrido[4,5-d]pyrimidin-4(3H)-one dichloro­methane solvate

Liu, J.-C.

doi:10.1107/S1600536807054013

3-(4-Chlorophenyl)-2-(2,4-dichlorophenoxy)-5-methyl-8,9,10,11-tetrahydro-2-benzothieno[2',3':2,3]pyrido[4,5-d]pyrimidin-4(3H)-one dichloromethane solvate

In the structure of the title compound, C₂₆H₁₈Cl₃N₃O₂S·CH₂Cl₂, the C-S bond lengths in the thiophene ring [1.733 (5) and 1.735 (5) Å] are equivalent and long compared with the values observed in both free thiophene, measured using electron diffraction, and thieno[2,3-c]pyridine. The central thienopyridine ring system is planar. The pyrimidinone ring forms a dihedral angle of 3.1 (2)° with the pyridine ring. The chloro- and dichlorophenyl rings form dihedral angles of 75.2 (2) and 85.5 (2)°, respectively, with the pyrimidinone ring. The dihedral angle between the chlorophenyl rings is 69.7 (2)°. The cyclohexene ring adopts a half-chair conformation. There is a C-H-O hydrogen bond between the main molecule and the dichoromethane molecule. The dichloromethane molecule is disordered over two positions, with refined occupancies of 0.775 (6) and 0.225 (6).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054013/ci2481sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054013/ci2481Isup2.hkl Contains datablock I

CCDC reference: 623908

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.007 Å
Disorder in solvent or counterion
R factor = 0.078
wR factor = 0.234
Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT221_ALERT_4_C Large Solvent/Anion  C     Ueq(max)/Ueq(min) ...       3.44 Ratio
PLAT221_ALERT_4_C Large Solvent/Anion Cl     Ueq(max)/Ueq(min) ...       3.94 Ratio
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.46 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C27
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C27'
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         41

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The pyridopyrimidine scaffold is a well known pharmacophore in drug design and it is associated with a wide range of biological properties. For example, many pyrido[4,3-d]pyrimidines have been described as inhibitors of tyrosine kinases of the epidermal growth factor receptor family (Bridges et al., 1997). An important synthetic route to pyrido[4,3-d]pyrimidine is the condensation reaction of 4-aminonicotinic acid and amines (Ismail & Wibberley, 1967). However, this method often require long reaction time. Recently, we have developed a new and facile regioselective annulation process, which proceeds smoothly under mild condition via a tandem aza-Wittig and cyclization reaction, to synthesize novel pyrido[4,3-d]pyrimidine derivates (Liu et al., 2006). In this paper, the crystal structure of the title compound is reported. The structure of the title compound was also characterized by ¹H NMR, MS and elemental analysis.

The molecular structure of (1) is shown in Fig. 1. The C—S bond lengths in the thiophene ring [1.733 (5) and 1.735 (5) Å] are almost equal and long compared with the values observed in free thiophene (1.714 Å; Bonham & Momany, 1963). The C8—S1—C5 [91.7 (2)°] angle is comparable to that observed in free thiophene [92.2 (2)°]. The C8—N1—C9 angle of 116.9 (4)° is typical of a non-protonated ring system, being smaller than 120° (Ghosh & Simonsen, 1993). The central thienopyridine ring system is nearly planar and the dihedral angle between the thiophene and pyridine planes is 1.6 (2)°. The pyrimidinone ring forms a dihedral angle of 3.1 (2)° with the pyridine ring. The chloro- and dichloro-phenyl rings form dihedral angles of 75.2 (2) and 85.5 (2)°, respectively, with the pyrimidinone ring. The dihedral angle between the chlorophenyl rings is 69.7 (2)°. The cyclohexene ring adopts a half-chair conformation. There exists a C27—H27A—O1 hydrogen bond between the main molecule and the dichoromethane molecule.

Related literature top

For related literature, see: Bonham & Momany (1963); Bridges et al. (1997); Ghosh & Simonsen (1993); Ismail & Wibberley (1967); Liu et al. (2006).

Experimental top

The title compound was prepared according to the literature procedure of Liu et al. (2006) and suitable crystals were obtained by evaporation of a dichoromethane solution (m.p. 563–565 K). Analysis, calculated for C₂₇H₂₀Cl₅N₃O₂S: C 51.66, H 3.31, N 6.69%; found: C 51.71, H 3.40, N 6.78%. IR (KBr, ν, cm^-1): 3125(Ph—H), 2931,2863(C—H), 1705(C=O), 1620, 1562, 1517, 1490, 1365, 1252, 1092, 843. ¹H NMR(CDCl₃, TMS, 400 MHz): 1.62–1.80(m, 4H, 2CH₂), 2.34–2.79(m, 4H, 2CH₂), 3.03(s, 3H, CH₃), 7.15–7.58(m, 7H, Ar—H). MS(EI, %): 544 (100), 543(M⁺ 90), 396 (16), 380 (20).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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, 1998); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probablity displacement ellipsoids.

3-(4-Chlorophenyl)-2-(2,4-dichlorophenoxy)-5-methyl-8,9,10,11-tetrahydro- 2-benzothieno[2',3':2,3]pyrido[4,5-d]pyrimidin-4(3H)-one dichloromethane solvate top

Crystal data top

C₂₆H₁₈Cl₃N₃O₂S·CH₂Cl₂	F(000) = 2560
M_r = 627.77	D_x = 1.495 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3031 reflections
a = 18.295 (6) Å	θ = 2.2–19.0°
b = 10.851 (4) Å	µ = 0.63 mm⁻¹
c = 28.097 (9) Å	T = 292 K
V = 5578 (3) Å³	Block, colourless
Z = 8	0.20 × 0.16 × 0.12 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5488 independent reflections
Radiation source: fine-focus sealed tube	3296 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→22
T_min = 0.885, T_max = 0.929	k = −13→13
29034 measured reflections	l = −22→34

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.234	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1242P)² + 1.4543P] where P = (F_o² + 2F_c²)/3
5488 reflections	(Δ/σ)_max = 0.001
372 parameters	Δρ_max = 0.64 e Å⁻³
41 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₂₆H₁₈Cl₃N₃O₂S·CH₂Cl₂	V = 5578 (3) Å³
M_r = 627.77	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 18.295 (6) Å	µ = 0.63 mm⁻¹
b = 10.851 (4) Å	T = 292 K
c = 28.097 (9) Å	0.20 × 0.16 × 0.12 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5488 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3296 reflections with I > 2σ(I)
T_min = 0.885, T_max = 0.929	R_int = 0.079
29034 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	41 restraints
wR(F²) = 0.234	H-atom parameters constrained
S = 1.04	Δρ_max = 0.64 e Å⁻³
5488 reflections	Δρ_min = −0.52 e Å⁻³
372 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.21511 (7)	0.80443 (11)	0.23989 (5)	0.0657 (4)
O1	0.3537 (2)	0.4856 (4)	0.05713 (12)	0.0791 (11)
O2	0.49710 (15)	0.3654 (3)	0.17882 (10)	0.0512 (7)
N1	0.2325 (2)	0.7211 (4)	0.15028 (16)	0.0623 (11)
N2	0.42421 (19)	0.4285 (3)	0.11922 (12)	0.0476 (9)
N3	0.40778 (18)	0.5042 (3)	0.19699 (11)	0.0427 (8)
Cl1	0.60808 (11)	0.10969 (19)	−0.00222 (6)	0.1144 (7)
Cl2	0.61639 (11)	0.41703 (16)	0.37059 (5)	0.1062 (7)
Cl3	0.61136 (8)	0.55092 (12)	0.18665 (5)	0.0791 (5)
C1	0.3714 (2)	0.5894 (4)	0.29686 (16)	0.0510 (11)
H1A	0.4207	0.6198	0.2920	0.061*
H1B	0.3707	0.5026	0.2886	0.061*
C2	0.3508 (3)	0.6043 (5)	0.34868 (18)	0.0732 (15)
H2A	0.3103	0.5496	0.3556	0.088*
H2B	0.3918	0.5785	0.3681	0.088*
C3	0.3304 (3)	0.7282 (5)	0.3624 (2)	0.0808 (16)
H3A	0.3719	0.7825	0.3578	0.097*
H3B	0.3182	0.7289	0.3960	0.097*
C4	0.2656 (3)	0.7775 (5)	0.33410 (19)	0.0667 (13)
H4A	0.2205	0.7449	0.3472	0.080*
H4B	0.2640	0.8666	0.3366	0.080*
C5	0.2719 (2)	0.7413 (4)	0.28293 (17)	0.0541 (11)
C6	0.3202 (2)	0.6575 (3)	0.26505 (16)	0.0460 (10)
C7	0.3112 (2)	0.6435 (4)	0.21415 (15)	0.0447 (10)
C8	0.2551 (2)	0.7161 (4)	0.19556 (17)	0.0536 (11)
C9	0.2674 (2)	0.6507 (5)	0.11937 (17)	0.0609 (13)
C10	0.3273 (2)	0.5734 (4)	0.13337 (15)	0.0494 (11)
C11	0.2414 (3)	0.6608 (7)	0.06876 (19)	0.0904 (19)
H11A	0.2814	0.6845	0.0487	0.136*
H11B	0.2035	0.7217	0.0668	0.136*
H11C	0.2226	0.5826	0.0585	0.136*
C12	0.3655 (2)	0.4967 (4)	0.09934 (17)	0.0559 (11)
C13	0.3492 (2)	0.5717 (3)	0.18081 (14)	0.0423 (10)
C14	0.4672 (2)	0.3507 (4)	0.08798 (15)	0.0507 (11)
C15	0.4589 (3)	0.2252 (4)	0.08967 (17)	0.0594 (12)
H15	0.4249	0.1902	0.1102	0.071*
C16	0.5012 (3)	0.1510 (5)	0.06094 (18)	0.0699 (14)
H16	0.4957	0.0658	0.0616	0.084*
C17	0.5513 (3)	0.2048 (6)	0.03150 (18)	0.0717 (15)
C18	0.5596 (3)	0.3282 (6)	0.02942 (18)	0.0747 (15)
H18	0.5939	0.3626	0.0089	0.090*
C19	0.5168 (3)	0.4039 (5)	0.05788 (17)	0.0650 (13)
H19	0.5218	0.4891	0.0565	0.078*
C20	0.4402 (2)	0.4372 (4)	0.16607 (15)	0.0445 (10)
C21	0.5227 (2)	0.3813 (4)	0.22526 (14)	0.0427 (10)
C22	0.4961 (2)	0.3099 (4)	0.26109 (16)	0.0540 (11)
H22	0.4590	0.2534	0.2553	0.065*
C23	0.5249 (3)	0.3223 (5)	0.30592 (17)	0.0631 (13)
H23	0.5068	0.2749	0.3309	0.076*
C24	0.5799 (3)	0.4040 (5)	0.31384 (17)	0.0627 (13)
C25	0.6071 (3)	0.4726 (4)	0.27805 (19)	0.0623 (13)
H25	0.6455	0.5269	0.2837	0.075*
C26	0.5783 (2)	0.4624 (4)	0.23344 (16)	0.0528 (11)
C27	0.6539 (11)	0.7036 (15)	0.0314 (6)	0.249 (11)	0.775 (6)
H27A	0.6307	0.6766	0.0022	0.298*	0.775 (6)
H27B	0.6912	0.7639	0.0237	0.298*	0.775 (6)
Cl4	0.5897 (7)	0.7657 (11)	0.0703 (3)	0.335 (6)	0.775 (6)
Cl5	0.6906 (2)	0.5827 (6)	0.06091 (14)	0.211 (3)	0.775 (6)
C27'	0.6306 (10)	0.731 (2)	0.0331 (7)	0.072 (7)	0.225 (6)
H27C	0.6128	0.7420	0.0009	0.086*	0.225 (6)
H27D	0.6482	0.6468	0.0368	0.086*	0.225 (6)
Cl5'	0.6977 (11)	0.838 (2)	0.0475 (7)	0.267 (11)	0.225 (6)
Cl4'	0.5647 (6)	0.7663 (8)	0.0747 (3)	0.085 (3)	0.225 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0499 (7)	0.0544 (7)	0.0928 (10)	0.0157 (6)	0.0065 (6)	0.0087 (6)
O1	0.082 (3)	0.109 (3)	0.047 (2)	0.015 (2)	−0.0146 (17)	0.0038 (19)
O2	0.0472 (17)	0.0563 (17)	0.0500 (18)	0.0139 (14)	−0.0046 (13)	−0.0038 (14)
N1	0.044 (2)	0.071 (3)	0.071 (3)	0.0063 (19)	−0.001 (2)	0.024 (2)
N2	0.046 (2)	0.053 (2)	0.043 (2)	0.0004 (16)	−0.0011 (16)	0.0026 (16)
N3	0.0421 (19)	0.0427 (18)	0.043 (2)	0.0042 (15)	−0.0007 (15)	0.0063 (16)
Cl1	0.1140 (14)	0.1339 (15)	0.0954 (13)	0.0158 (11)	0.0231 (10)	−0.0474 (11)
Cl2	0.1456 (16)	0.1045 (12)	0.0685 (10)	0.0484 (11)	−0.0462 (9)	−0.0280 (8)
Cl3	0.0886 (10)	0.0617 (8)	0.0870 (10)	−0.0128 (7)	0.0238 (7)	0.0028 (7)
C1	0.050 (2)	0.043 (2)	0.061 (3)	0.0013 (19)	−0.004 (2)	−0.001 (2)
C2	0.089 (4)	0.072 (3)	0.059 (3)	0.007 (3)	−0.006 (3)	0.002 (3)
C3	0.084 (4)	0.089 (4)	0.069 (4)	0.000 (3)	0.007 (3)	−0.018 (3)
C4	0.057 (3)	0.057 (3)	0.085 (4)	0.002 (2)	0.009 (3)	−0.012 (3)
C5	0.050 (3)	0.048 (2)	0.064 (3)	−0.004 (2)	0.009 (2)	0.003 (2)
C6	0.038 (2)	0.033 (2)	0.067 (3)	−0.0028 (17)	0.0056 (19)	0.0030 (19)
C7	0.033 (2)	0.043 (2)	0.058 (3)	−0.0026 (18)	0.0029 (18)	0.014 (2)
C8	0.042 (2)	0.048 (2)	0.071 (3)	−0.0013 (19)	0.005 (2)	0.017 (2)
C9	0.045 (3)	0.075 (3)	0.062 (3)	0.001 (2)	−0.006 (2)	0.023 (3)
C10	0.041 (2)	0.055 (3)	0.052 (3)	−0.001 (2)	−0.0029 (19)	0.015 (2)
C11	0.064 (3)	0.138 (5)	0.070 (4)	0.026 (4)	−0.014 (3)	0.030 (3)
C12	0.048 (3)	0.067 (3)	0.052 (3)	−0.004 (2)	−0.003 (2)	0.016 (2)
C13	0.037 (2)	0.039 (2)	0.051 (3)	−0.0041 (17)	−0.0036 (18)	0.0141 (18)
C14	0.048 (3)	0.062 (3)	0.042 (2)	−0.006 (2)	−0.0007 (19)	−0.001 (2)
C15	0.061 (3)	0.060 (3)	0.058 (3)	−0.013 (2)	0.004 (2)	−0.002 (2)
C16	0.070 (3)	0.071 (3)	0.069 (3)	−0.009 (3)	−0.002 (3)	−0.018 (3)
C17	0.070 (3)	0.091 (4)	0.053 (3)	0.000 (3)	0.000 (3)	−0.025 (3)
C18	0.069 (3)	0.102 (5)	0.053 (3)	−0.001 (3)	0.018 (3)	−0.003 (3)
C19	0.071 (3)	0.064 (3)	0.060 (3)	−0.007 (3)	0.013 (3)	0.004 (2)
C20	0.041 (2)	0.044 (2)	0.049 (3)	−0.0026 (19)	−0.0001 (19)	0.005 (2)
C21	0.043 (2)	0.043 (2)	0.042 (2)	0.0144 (19)	−0.0028 (18)	−0.0020 (18)
C22	0.050 (3)	0.053 (3)	0.058 (3)	0.008 (2)	−0.001 (2)	0.004 (2)
C23	0.078 (3)	0.059 (3)	0.053 (3)	0.019 (3)	0.004 (2)	0.011 (2)
C24	0.077 (3)	0.057 (3)	0.055 (3)	0.027 (3)	−0.017 (3)	−0.015 (2)
C25	0.057 (3)	0.055 (3)	0.075 (4)	0.007 (2)	−0.012 (3)	−0.014 (3)
C26	0.050 (3)	0.045 (2)	0.064 (3)	0.007 (2)	0.008 (2)	−0.004 (2)
C27	0.278 (14)	0.259 (13)	0.208 (13)	−0.023 (10)	0.037 (10)	0.018 (9)
Cl4	0.387 (12)	0.353 (10)	0.266 (8)	0.012 (9)	−0.060 (8)	−0.009 (8)
Cl5	0.132 (3)	0.355 (7)	0.148 (3)	−0.034 (3)	−0.025 (2)	−0.082 (4)
C27'	0.070 (10)	0.098 (11)	0.047 (9)	−0.004 (8)	0.040 (8)	−0.002 (8)
Cl5'	0.300 (19)	0.288 (18)	0.213 (15)	−0.001 (15)	−0.024 (13)	0.008 (13)
Cl4'	0.127 (6)	0.092 (5)	0.037 (4)	0.006 (4)	0.029 (4)	−0.001 (3)

Geometric parameters (Å, º) top

S1—C8	1.733 (5)	C9—C11	1.504 (7)
S1—C5	1.735 (5)	C10—C13	1.392 (6)
O1—C12	1.211 (5)	C10—C12	1.447 (7)
O2—C20	1.349 (5)	C11—H11A	0.96
O2—C21	1.397 (5)	C11—H11B	0.96
N1—C9	1.321 (6)	C11—H11C	0.96
N1—C8	1.338 (6)	C14—C19	1.369 (6)
N2—C20	1.352 (5)	C14—C15	1.372 (6)
N2—C12	1.419 (6)	C15—C16	1.377 (7)
N2—C14	1.449 (5)	C15—H15	0.93
N3—C20	1.279 (5)	C16—C17	1.367 (8)
N3—C13	1.375 (5)	C16—H16	0.93
Cl1—C17	1.744 (5)	C17—C18	1.349 (8)
Cl2—C24	1.735 (5)	C18—C19	1.387 (7)
Cl3—C26	1.737 (5)	C18—H18	0.93
C1—C6	1.490 (6)	C19—H19	0.93
C1—C2	1.513 (7)	C21—C22	1.360 (6)
C1—H1A	0.97	C21—C26	1.364 (6)
C1—H1B	0.97	C22—C23	1.372 (6)
C2—C3	1.447 (7)	C22—H22	0.93
C2—H2A	0.97	C23—C24	1.358 (7)
C2—H2B	0.97	C23—H23	0.93
C3—C4	1.525 (7)	C24—C25	1.347 (7)
C3—H3A	0.97	C25—C26	1.364 (6)
C3—H3B	0.97	C25—H25	0.93
C4—C5	1.495 (7)	C27—Cl5	1.691 (9)
C4—H4A	0.97	C27—Cl4	1.739 (9)
C4—H4B	0.97	C27—H27A	0.97
C5—C6	1.364 (6)	C27—H27B	0.97
C6—C7	1.448 (6)	C27'—Cl4'	1.724 (9)
C7—C8	1.396 (6)	C27'—Cl5'	1.740 (9)
C7—C13	1.403 (6)	C27'—H27C	0.97
C9—C10	1.435 (6)	C27'—H27D	0.97

C8—S1—C5	91.7 (2)	O1—C12—C10	128.2 (4)
C20—O2—C21	115.8 (3)	N2—C12—C10	113.9 (4)
C9—N1—C8	116.9 (4)	N3—C13—C10	123.2 (4)
C20—N2—C12	120.7 (4)	N3—C13—C7	117.5 (4)
C20—N2—C14	120.9 (3)	C10—C13—C7	119.3 (4)
C12—N2—C14	118.4 (4)	C19—C14—C15	120.8 (4)
C20—N3—C13	116.1 (3)	C19—C14—N2	119.3 (4)
C6—C1—C2	111.6 (4)	C15—C14—N2	119.8 (4)
C6—C1—H1A	109.3	C14—C15—C16	119.9 (5)
C2—C1—H1A	109.3	C14—C15—H15	120.0
C6—C1—H1B	109.3	C16—C15—H15	120.0
C2—C1—H1B	109.3	C17—C16—C15	118.8 (5)
H1A—C1—H1B	108.0	C17—C16—H16	120.6
C3—C2—C1	114.9 (4)	C15—C16—H16	120.6
C3—C2—H2A	108.6	C18—C17—C16	121.7 (5)
C1—C2—H2A	108.5	C18—C17—Cl1	119.8 (4)
C3—C2—H2B	108.5	C16—C17—Cl1	118.4 (5)
C1—C2—H2B	108.5	C17—C18—C19	119.9 (5)
H2A—C2—H2B	107.5	C17—C18—H18	120.0
C2—C3—C4	112.8 (5)	C19—C18—H18	120.0
C2—C3—H3A	109.0	C14—C19—C18	118.8 (5)
C4—C3—H3A	109.0	C14—C19—H19	120.6
C2—C3—H3B	109.0	C18—C19—H19	120.6
C4—C3—H3B	109.0	N3—C20—O2	120.4 (4)
H3A—C3—H3B	107.8	N3—C20—N2	126.9 (4)
C5—C4—C3	110.5 (4)	O2—C20—N2	112.6 (4)
C5—C4—H4A	109.6	C22—C21—C26	120.6 (4)
C3—C4—H4A	109.6	C22—C21—O2	120.1 (4)
C5—C4—H4B	109.6	C26—C21—O2	119.2 (4)
C3—C4—H4B	109.6	C21—C22—C23	119.1 (5)
H4A—C4—H4B	108.1	C21—C22—H22	120.4
C6—C5—C4	125.4 (4)	C23—C22—H22	120.4
C6—C5—S1	113.2 (4)	C24—C23—C22	119.9 (5)
C4—C5—S1	121.4 (3)	C24—C23—H23	120.0
C5—C6—C7	111.1 (4)	C22—C23—H23	120.0
C5—C6—C1	121.1 (4)	C25—C24—C23	120.8 (5)
C7—C6—C1	127.7 (4)	C25—C24—Cl2	119.9 (4)
C8—C7—C13	115.4 (4)	C23—C24—Cl2	119.3 (4)
C8—C7—C6	113.2 (4)	C24—C25—C26	119.8 (5)
C13—C7—C6	131.4 (4)	C24—C25—H25	120.1
N1—C8—C7	127.2 (4)	C26—C25—H25	120.1
N1—C8—S1	122.1 (3)	C21—C26—C25	119.7 (4)
C7—C8—S1	110.7 (4)	C21—C26—Cl3	119.2 (4)
N1—C9—C10	121.8 (4)	C25—C26—Cl3	121.0 (4)
N1—C9—C11	115.3 (4)	Cl5—C27—Cl4	105.1 (9)
C10—C9—C11	122.9 (5)	Cl5—C27—H27A	110.7
C13—C10—C9	119.3 (4)	Cl4—C27—H27A	110.7
C13—C10—C12	119.1 (4)	Cl5—C27—H27B	110.7
C9—C10—C12	121.6 (4)	Cl4—C27—H27B	110.7
C9—C11—H11A	109.5	H27A—C27—H27B	108.8
C9—C11—H11B	109.5	Cl4'—C27'—Cl5'	100.7 (10)
H11A—C11—H11B	109.5	Cl4'—C27'—H27C	111.6
C9—C11—H11C	109.5	Cl5'—C27'—H27C	111.6
H11A—C11—H11C	109.5	Cl4'—C27'—H27D	111.6
H11B—C11—H11C	109.5	Cl5'—C27'—H27D	111.6
O1—C12—N2	117.9 (4)	H27C—C27'—H27D	109.4

C6—C1—C2—C3	−43.0 (6)	C9—C10—C13—C7	1.3 (6)
C1—C2—C3—C4	58.8 (7)	C12—C10—C13—C7	−178.4 (4)
C2—C3—C4—C5	−40.6 (6)	C8—C7—C13—N3	176.2 (3)
C3—C4—C5—C6	11.5 (7)	C6—C7—C13—N3	−3.0 (6)
C3—C4—C5—S1	−169.1 (4)	C8—C7—C13—C10	−2.5 (5)
C8—S1—C5—C6	0.8 (3)	C6—C7—C13—C10	178.3 (4)
C8—S1—C5—C4	−178.7 (4)	C20—N2—C14—C19	−103.7 (5)
C4—C5—C6—C7	179.5 (4)	C12—N2—C14—C19	75.4 (5)
S1—C5—C6—C7	0.1 (4)	C20—N2—C14—C15	74.8 (5)
C4—C5—C6—C1	2.1 (7)	C12—N2—C14—C15	−106.1 (5)
S1—C5—C6—C1	−177.4 (3)	C19—C14—C15—C16	0.2 (7)
C2—C1—C6—C5	12.5 (6)	N2—C14—C15—C16	−178.2 (4)
C2—C1—C6—C7	−164.5 (4)	C14—C15—C16—C17	0.7 (7)
C5—C6—C7—C8	−1.2 (5)	C15—C16—C17—C18	−1.0 (8)
C1—C6—C7—C8	176.1 (4)	C15—C16—C17—Cl1	176.4 (4)
C5—C6—C7—C13	178.1 (4)	C16—C17—C18—C19	0.4 (9)
C1—C6—C7—C13	−4.7 (7)	Cl1—C17—C18—C19	−177.0 (4)
C9—N1—C8—C7	−0.7 (7)	C15—C14—C19—C18	−0.8 (7)
C9—N1—C8—S1	179.3 (3)	N2—C14—C19—C18	177.6 (4)
C13—C7—C8—N1	2.3 (6)	C17—C18—C19—C14	0.5 (8)
C6—C7—C8—N1	−178.3 (4)	C13—N3—C20—O2	−178.3 (3)
C13—C7—C8—S1	−177.6 (3)	C13—N3—C20—N2	1.9 (6)
C6—C7—C8—S1	1.7 (4)	C21—O2—C20—N3	−7.7 (5)
C5—S1—C8—N1	178.6 (4)	C21—O2—C20—N2	172.2 (3)
C5—S1—C8—C7	−1.4 (3)	C12—N2—C20—N3	−0.7 (6)
C8—N1—C9—C10	−0.7 (7)	C14—N2—C20—N3	178.3 (4)
C8—N1—C9—C11	−178.9 (4)	C12—N2—C20—O2	179.5 (3)
N1—C9—C10—C13	0.4 (7)	C14—N2—C20—O2	−1.5 (5)
C11—C9—C10—C13	178.4 (5)	C20—O2—C21—C22	92.4 (4)
N1—C9—C10—C12	−179.9 (4)	C20—O2—C21—C26	−92.6 (4)
C11—C9—C10—C12	−1.8 (7)	C26—C21—C22—C23	1.4 (6)
C20—N2—C12—O1	179.8 (4)	O2—C21—C22—C23	176.4 (4)
C14—N2—C12—O1	0.7 (6)	C21—C22—C23—C24	−0.9 (7)
C20—N2—C12—C10	0.5 (6)	C22—C23—C24—C25	−0.5 (7)
C14—N2—C12—C10	−178.6 (4)	C22—C23—C24—Cl2	−179.2 (3)
C13—C10—C12—O1	179.3 (5)	C23—C24—C25—C26	1.5 (7)
C9—C10—C12—O1	−0.4 (8)	Cl2—C24—C25—C26	−179.9 (3)
C13—C10—C12—N2	−1.6 (6)	C22—C21—C26—C25	−0.5 (6)
C9—C10—C12—N2	178.7 (4)	O2—C21—C26—C25	−175.6 (4)
C20—N3—C13—C10	−3.0 (6)	C22—C21—C26—Cl3	179.4 (3)
C20—N3—C13—C7	178.3 (3)	O2—C21—C26—Cl3	4.4 (5)
C9—C10—C13—N3	−177.3 (4)	C24—C25—C26—C21	−0.9 (7)
C12—C10—C13—N3	2.9 (6)	C24—C25—C26—Cl3	179.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27A···O1ⁱ	0.97	2.44	3.23 (2)	138

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈Cl₃N₃O₂S·CH₂Cl₂
M_r	627.77
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	292
a, b, c (Å)	18.295 (6), 10.851 (4), 28.097 (9)
V (Å³)	5578 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.885, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	29034, 5488, 3296
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.234, 1.04
No. of reflections	5488
No. of parameters	372
No. of restraints	41
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.52

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