Ethyl 8-amino-2-(o-tol­yloxy)-4-oxo-3-phenyl-3,4-dihydro­thieno[2′,3′:2,3]thieno[4,5-d]pyrimidine-6-carboxyl­ate

Liu, M.-G.; Ma, Z.; Xie, T.; Yang, Z.-Z.

doi:10.1107/S1600536807036781

Ethyl 8-amino-2-(o-tolyloxy)-4-oxo-3-phenyl-3,4-dihydrothieno[2′,3′:2,3]thieno[4,5-d]pyrimidine-6-carboxylate

In the title compound, C₂₄H₁₉N₃O₄S₂, the fused thienothienopyrimidine ring system is essentially planar, and makes a dihedral angle of 85.61 (2) and 72.02 (2)° with the phenyl and o-tolyloxy rings, respectively. The molecular structure is stabilized by intramolecular N—H

N and N—H

O hydrogen bonds. The crystal packing is stabilized mainly by intermolecular π–π interactions between adjacent thienothienopyrimidine ring systems; the centroid–centroid distances between the central and outer thiophene rings and between adjacent outer thiophene rings are 3.841 (4) and 3.696 (4) Å, respectively.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036781/is2198sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036781/is2198Isup2.hkl Contains datablock I

CCDC reference: 657891

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.007 Å
R factor = 0.067
wR factor = 0.179
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.90 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C15     ..       6.11 su
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        C23
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The derivatives of thienopyrimidine are of great importance because of their remarked biological properties (Panico et al., 2001; Ding et al., 2004; Modica et al., 2004). We have recently focused on the synthesis of fused heterocyclic systems containing a fused pyrimidinone ring moiety using aza-Wittig reaction (Liu et al., 2006). The title compound, (I), may be used as a new precursor for obtaining bioactive molecules and its structure is reported here (Fig. 1). The bond lengths and angles are unexceptional. The thienothienopyrimidinone ring system is essentially planar, with maximum deviations 0.034 (1) and 0.021 (3) Å for S1 and C20, respectively; the C1—C6 phenyl ring is twisted with respect to it, with a dihedral angle of 85.61 (2)°. Intramolecular N—H···O and N—H···N hydrogen bonds interactions are present which stabilize the molecular structure (Table 1). There are also intermolecular π-π interactions (Janiak, 2000; Fig. 2). In the thienothiophene system (ring A: S1/C18/C19/C20/C21 and B: S2/C10/C9/C19/C18), the interplanar perpendicular distances between them A/Aⁱ and A/Bⁱ [symmetry code (i): 2 - x, 2 - y, 2 - z] are 3.490 (3) and 3.471 (3) Å, respectively, and the center-to-center distances are 3.696 (4) and 3.841 (4) Å.

Related literature top

Many derivatives of pyrimidinone have been prepared, and their biological and pharmaceutical activities have been studied by Modica et al. (2004) and Panico et al. (2001). For related literature, see: Janiak (2000); Ding et al. (2004); Liu et al. (2006).

Experimental top

To a solution of diethyl 3-triphenylphosphoranylideneamino- 4-aminothieno[2,3-b]thiophene-2,5-dicarboxylate (3 mmol) in anhydrous dichloromethane (15 ml) was added phenyl isocyanate (3 mmol) under dry nitrogen at room temperature. The reaction mixture was left unstirred for 8 h at 273–278 K, then the solvent was removed under reduced pressure, which was used directly without further purification. To the reaction mixture was added anhydrous acetonitrile (15 ml) with 2-methylphenol (3 mmol) and anhydrous K₂CO₃ (1 mmol). The mixture was stirred for 6 h at 313–323 K, the solution concentrated under reduced pressure. The title compound was recrystallized from ethanol/dichloromethane (1:2 v/v) at room temperature, yielding single crystals suitable for X-ray diffraction.

Structure description top

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. The intramolecular N—H···N/O hydrogen bonds are indicated by dashed lines.
	Fig. 2. A packing view of the title compound along the a axis, showing the hydrogen bonds as dashed lines.

Ethyl 8-amino-2-(o-tolyloxy)-4-oxo-3-phenyl-3,4-dihydro- thieno[2',3':2,3]thieno[4,5-d]pyrimidine-6-carboxylate top

Crystal data top

C₂₄H₁₉N₃O₄S₂	Z = 2
M_r = 477.54	F(000) = 496
Triclinic, P1	D_x = 1.382 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0996 (6) Å	Cell parameters from 2292 reflections
b = 10.444 (9) Å	θ = 2.1–22.0°
c = 16.9985 (13) Å	µ = 0.27 mm⁻¹
α = 104.447 (1)°	T = 292 K
β = 97.120 (1)°	Plate, colorless
γ = 106.041 (1)°	0.30 × 0.20 × 0.10 mm
V = 1147.5 (10) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3980 independent reflections
Radiation source: fine-focus sealed tube	2644 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
φ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.924, T_max = 0.974	k = −12→12
9743 measured reflections	l = −20→20

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0925P)²] where P = (F_o² + 2F_c²)/3
3980 reflections	(Δ/σ)_max = 0.001
300 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₄H₁₉N₃O₄S₂	γ = 106.041 (1)°
M_r = 477.54	V = 1147.5 (10) Å³
Triclinic, P1	Z = 2
a = 7.0996 (6) Å	Mo Kα radiation
b = 10.444 (9) Å	µ = 0.27 mm⁻¹
c = 16.9985 (13) Å	T = 292 K
α = 104.447 (1)°	0.30 × 0.20 × 0.10 mm
β = 97.120 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3980 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2644 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.974	R_int = 0.058
9743 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.04	Δρ_max = 0.27 e Å⁻³
3980 reflections	Δρ_min = −0.32 e Å⁻³
300 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
C1	0.9189 (7)	1.1256 (5)	0.6229 (3)	0.0784 (14)
H1	1.0236	1.1054	0.6504	0.094*
C2	0.9250 (9)	1.1479 (6)	0.5454 (3)	0.1021 (19)
H2	1.0353	1.1441	0.5217	0.122*
C3	0.7701 (11)	1.1754 (5)	0.5041 (3)	0.0965 (19)
H3	0.7751	1.1906	0.4527	0.116*
C4	0.6068 (10)	1.1805 (5)	0.5392 (3)	0.0949 (18)
H4	0.5012	1.1990	0.5110	0.114*
C5	0.5974 (8)	1.1584 (4)	0.6161 (3)	0.0774 (14)
H5	0.4855	1.1602	0.6390	0.093*
C6	0.7567 (6)	1.1337 (4)	0.6580 (2)	0.0543 (10)
C7	0.8496 (5)	1.2306 (4)	0.8098 (2)	0.0451 (9)
C8	0.6680 (5)	0.9832 (3)	0.7488 (2)	0.0447 (9)
C9	0.7561 (5)	1.0601 (3)	0.88721 (19)	0.0388 (8)
C10	0.8443 (5)	1.1936 (4)	0.8855 (2)	0.0456 (9)
C11	0.5062 (6)	0.7475 (4)	0.6740 (2)	0.0509 (10)
C12	0.3264 (7)	0.7053 (5)	0.6964 (3)	0.0694 (12)
H12	0.2603	0.7684	0.7157	0.083*
C13	0.2456 (8)	0.5640 (6)	0.6891 (3)	0.0939 (17)
H13	0.1256	0.5314	0.7055	0.113*
C14	0.3440 (12)	0.4740 (5)	0.6578 (4)	0.111 (2)
H14	0.2881	0.3792	0.6508	0.133*
C15	0.5262 (10)	0.5225 (5)	0.6362 (4)	0.1013 (18)
H15	0.5923	0.4595	0.6164	0.122*
C16	0.6118 (7)	0.6600 (4)	0.6431 (3)	0.0647 (11)
C17	0.8087 (8)	0.7118 (6)	0.6181 (4)	0.113 (2)
H17A	0.9056	0.7778	0.6655	0.170*
H17B	0.7907	0.7561	0.5758	0.170*
H17C	0.8553	0.6345	0.5969	0.170*
C18	0.8776 (5)	1.1747 (4)	1.0281 (2)	0.0447 (9)
C19	0.7735 (5)	1.0482 (3)	0.9699 (2)	0.0406 (8)
C20	0.7077 (5)	0.9386 (4)	1.0068 (2)	0.0435 (8)
C21	0.7692 (5)	0.9872 (4)	1.0933 (2)	0.0472 (9)
C22	0.7380 (6)	0.9123 (4)	1.1549 (2)	0.0517 (9)
C23	0.6039 (7)	0.6880 (4)	1.1759 (2)	0.0606 (11)
H23A	0.7302	0.6987	1.2104	0.073*
H23B	0.5168	0.7154	1.2118	0.073*
C24	0.5102 (9)	0.5422 (5)	1.1241 (3)	0.1020 (18)
H24A	0.3903	0.5341	1.0875	0.153*
H24B	0.4775	0.4834	1.1591	0.153*
H24C	0.6018	0.5140	1.0920	0.153*
N1	0.7524 (4)	1.1129 (3)	0.74015 (16)	0.0473 (7)
O1	0.9230 (4)	1.3454 (3)	0.80035 (16)	0.0630 (8)
N2	0.6637 (4)	0.9504 (3)	0.81807 (16)	0.0436 (7)
O2	0.5882 (4)	0.8878 (2)	0.67519 (14)	0.0580 (7)
N3	0.6009 (5)	0.8069 (3)	0.96004 (18)	0.0546 (8)
H3A	0.5636	0.7426	0.9835	0.066*
H3B	0.5702	0.7873	0.9069	0.066*
O4	0.7953 (5)	0.9629 (3)	1.22886 (16)	0.0710 (8)
O5	0.6378 (4)	0.7756 (3)	1.11951 (15)	0.0570 (7)
S1	0.90384 (15)	1.16428 (10)	1.12772 (6)	0.0569 (3)
S2	0.95315 (15)	1.30932 (10)	0.98436 (6)	0.0562 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.065 (3)	0.109 (4)	0.055 (3)	0.007 (3)	0.010 (2)	0.040 (3)
C2	0.090 (4)	0.135 (5)	0.067 (3)	−0.001 (4)	0.017 (3)	0.047 (3)
C3	0.136 (5)	0.088 (4)	0.052 (3)	0.007 (4)	0.004 (3)	0.038 (3)
C4	0.149 (6)	0.094 (4)	0.053 (3)	0.064 (4)	−0.010 (3)	0.027 (3)
C5	0.110 (4)	0.080 (3)	0.052 (3)	0.055 (3)	0.003 (3)	0.017 (2)
C6	0.075 (3)	0.042 (2)	0.042 (2)	0.0100 (19)	0.002 (2)	0.0180 (17)
C7	0.045 (2)	0.044 (2)	0.045 (2)	0.0117 (17)	0.0040 (16)	0.0163 (17)
C8	0.050 (2)	0.041 (2)	0.041 (2)	0.0144 (17)	0.0051 (16)	0.0103 (16)
C9	0.0333 (18)	0.049 (2)	0.0382 (18)	0.0165 (16)	0.0072 (15)	0.0161 (16)
C10	0.041 (2)	0.046 (2)	0.044 (2)	0.0119 (17)	0.0012 (16)	0.0091 (16)
C11	0.068 (3)	0.043 (2)	0.0343 (18)	0.0112 (19)	0.0013 (18)	0.0106 (16)
C12	0.066 (3)	0.079 (3)	0.060 (3)	0.014 (2)	0.014 (2)	0.023 (2)
C13	0.092 (4)	0.093 (4)	0.077 (3)	−0.013 (3)	0.011 (3)	0.040 (3)
C14	0.166 (7)	0.046 (3)	0.085 (4)	−0.007 (4)	−0.010 (4)	0.021 (3)
C15	0.139 (5)	0.058 (3)	0.104 (4)	0.031 (3)	0.026 (4)	0.019 (3)
C16	0.080 (3)	0.054 (3)	0.059 (3)	0.022 (2)	0.012 (2)	0.015 (2)
C17	0.096 (4)	0.137 (5)	0.128 (5)	0.056 (4)	0.049 (4)	0.042 (4)
C18	0.0339 (19)	0.056 (2)	0.0433 (19)	0.0166 (17)	0.0061 (15)	0.0109 (17)
C19	0.0374 (19)	0.048 (2)	0.0426 (19)	0.0195 (16)	0.0077 (16)	0.0186 (17)
C20	0.039 (2)	0.058 (2)	0.0403 (19)	0.0239 (18)	0.0071 (16)	0.0159 (17)
C21	0.043 (2)	0.058 (2)	0.044 (2)	0.0188 (18)	0.0059 (16)	0.0187 (17)
C22	0.053 (2)	0.067 (3)	0.044 (2)	0.029 (2)	0.0108 (18)	0.0201 (19)
C23	0.070 (3)	0.071 (3)	0.054 (2)	0.029 (2)	0.018 (2)	0.033 (2)
C24	0.146 (5)	0.076 (3)	0.070 (3)	0.011 (3)	0.010 (3)	0.030 (3)
N1	0.0583 (19)	0.0426 (17)	0.0393 (16)	0.0133 (15)	0.0054 (14)	0.0149 (13)
O1	0.0733 (19)	0.0456 (15)	0.0613 (17)	0.0070 (14)	0.0033 (14)	0.0189 (13)
N2	0.0517 (18)	0.0399 (16)	0.0371 (16)	0.0140 (14)	0.0038 (13)	0.0110 (13)
O2	0.086 (2)	0.0418 (14)	0.0378 (14)	0.0111 (13)	0.0043 (13)	0.0125 (11)
N3	0.066 (2)	0.0498 (18)	0.0440 (17)	0.0142 (16)	0.0050 (15)	0.0153 (14)
O4	0.092 (2)	0.0792 (19)	0.0401 (15)	0.0242 (16)	0.0034 (14)	0.0224 (14)
O5	0.0678 (18)	0.0602 (17)	0.0447 (14)	0.0181 (14)	0.0101 (13)	0.0222 (13)
S1	0.0593 (7)	0.0654 (7)	0.0403 (5)	0.0167 (5)	0.0036 (4)	0.0125 (5)
S2	0.0615 (7)	0.0490 (6)	0.0480 (6)	0.0095 (5)	0.0016 (5)	0.0109 (4)

Geometric parameters (Å, º) top

C1—C6	1.374 (6)	C13—H13	0.9300
C1—C2	1.398 (6)	C14—C15	1.382 (8)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.366 (8)	C15—C16	1.364 (6)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.375 (7)	C16—C17	1.508 (6)
C3—H3	0.9300	C17—H17A	0.9600
C4—C5	1.390 (6)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600
C5—C6	1.381 (6)	C18—C19	1.378 (5)
C5—H5	0.9300	C18—S1	1.715 (3)
C6—N1	1.468 (4)	C18—S2	1.738 (4)
C7—O1	1.227 (4)	C19—C20	1.434 (5)
C7—N1	1.411 (4)	C20—N3	1.352 (5)
C7—C10	1.436 (5)	C20—C21	1.400 (5)
C8—N2	1.307 (4)	C21—C22	1.458 (5)
C8—O2	1.330 (4)	C21—S1	1.738 (4)
C8—N1	1.375 (4)	C22—O4	1.204 (4)
C9—N2	1.359 (4)	C22—O5	1.345 (4)
C9—C10	1.371 (5)	C23—C24	1.470 (6)
C9—C19	1.434 (4)	C23—O5	1.480 (4)
C10—S2	1.740 (3)	C23—H23A	0.9700
C11—C12	1.364 (5)	C23—H23B	0.9700
C11—C16	1.382 (6)	C24—H24A	0.9600
C11—O2	1.414 (4)	C24—H24B	0.9600
C12—C13	1.395 (7)	C24—H24C	0.9600
C12—H12	0.9300	N3—H3A	0.8600
C13—C14	1.364 (8)	N3—H3B	0.8600

C6—C1—C2	119.3 (5)	C15—C16—C17	121.7 (5)
C6—C1—H1	120.3	C11—C16—C17	122.6 (4)
C2—C1—H1	120.3	C16—C17—H17A	109.5
C3—C2—C1	120.5 (5)	C16—C17—H17B	109.5
C3—C2—H2	119.7	H17A—C17—H17B	109.5
C1—C2—H2	119.7	C16—C17—H17C	109.5
C2—C3—C4	119.6 (5)	H17A—C17—H17C	109.5
C2—C3—H3	120.2	H17B—C17—H17C	109.5
C4—C3—H3	120.2	C19—C18—S1	112.8 (3)
C3—C4—C5	120.9 (5)	C19—C18—S2	113.0 (3)
C3—C4—H4	119.6	S1—C18—S2	134.2 (2)
C5—C4—H4	119.6	C18—C19—C9	111.4 (3)
C6—C5—C4	119.0 (5)	C18—C19—C20	112.5 (3)
C6—C5—H5	120.5	C9—C19—C20	136.0 (3)
C4—C5—H5	120.5	N3—C20—C21	127.0 (3)
C1—C6—C5	120.6 (4)	N3—C20—C19	121.6 (3)
C1—C6—N1	119.3 (4)	C21—C20—C19	111.4 (3)
C5—C6—N1	120.1 (4)	C20—C21—C22	129.9 (3)
O1—C7—N1	120.2 (3)	C20—C21—S1	111.7 (3)
O1—C7—C10	128.9 (3)	C22—C21—S1	118.4 (3)
N1—C7—C10	110.9 (3)	O4—C22—O5	122.4 (3)
N2—C8—O2	121.7 (3)	O4—C22—C21	125.6 (4)
N2—C8—N1	127.2 (3)	O5—C22—C21	112.0 (3)
O2—C8—N1	111.1 (3)	C24—C23—O5	107.6 (3)
N2—C9—C10	123.7 (3)	C24—C23—H23A	110.2
N2—C9—C19	123.5 (3)	O5—C23—H23A	110.2
C10—C9—C19	112.7 (3)	C24—C23—H23B	110.2
C9—C10—C7	122.9 (3)	O5—C23—H23B	110.2
C9—C10—S2	112.4 (3)	H23A—C23—H23B	108.5
C7—C10—S2	124.6 (3)	C23—C24—H24A	109.5
C12—C11—C16	124.7 (4)	C23—C24—H24B	109.5
C12—C11—O2	119.7 (4)	H24A—C24—H24B	109.5
C16—C11—O2	115.4 (3)	C23—C24—H24C	109.5
C11—C12—C13	117.5 (5)	H24A—C24—H24C	109.5
C11—C12—H12	121.2	H24B—C24—H24C	109.5
C13—C12—H12	121.2	C8—N1—C7	121.5 (3)
C14—C13—C12	119.4 (5)	C8—N1—C6	121.5 (3)
C14—C13—H13	120.3	C7—N1—C6	116.9 (3)
C12—C13—H13	120.3	C8—N2—C9	113.8 (3)
C13—C14—C15	120.6 (5)	C8—O2—C11	117.6 (3)
C13—C14—H14	119.7	C20—N3—H3A	120.0
C15—C14—H14	119.7	C20—N3—H3B	120.0
C16—C15—C14	121.9 (5)	H3A—N3—H3B	120.0
C16—C15—H15	119.1	C22—O5—C23	116.8 (3)
C14—C15—H15	119.1	C18—S1—C21	91.53 (17)
C15—C16—C11	115.7 (4)	C18—S2—C10	90.37 (17)

C6—C1—C2—C3	−1.0 (8)	N3—C20—C21—C22	0.5 (6)
C1—C2—C3—C4	−0.3 (8)	C19—C20—C21—C22	−179.1 (3)
C2—C3—C4—C5	0.2 (8)	N3—C20—C21—S1	180.0 (3)
C3—C4—C5—C6	1.2 (7)	C19—C20—C21—S1	0.3 (4)
C2—C1—C6—C5	2.4 (7)	C20—C21—C22—O4	−179.4 (4)
C2—C1—C6—N1	−178.8 (4)	S1—C21—C22—O4	1.2 (5)
C4—C5—C6—C1	−2.5 (6)	C20—C21—C22—O5	1.5 (5)
C4—C5—C6—N1	178.7 (4)	S1—C21—C22—O5	−177.9 (2)
N2—C9—C10—C7	−0.7 (5)	N2—C8—N1—C7	0.3 (6)
C19—C9—C10—C7	178.7 (3)	O2—C8—N1—C7	−178.9 (3)
N2—C9—C10—S2	−179.0 (3)	N2—C8—N1—C6	176.4 (4)
C19—C9—C10—S2	0.4 (4)	O2—C8—N1—C6	−2.8 (5)
O1—C7—C10—C9	179.8 (4)	O1—C7—N1—C8	−179.7 (3)
N1—C7—C10—C9	0.4 (5)	C10—C7—N1—C8	−0.2 (5)
O1—C7—C10—S2	−2.1 (6)	O1—C7—N1—C6	4.1 (5)
N1—C7—C10—S2	178.5 (3)	C10—C7—N1—C6	−176.4 (3)
C16—C11—C12—C13	1.4 (6)	C1—C6—N1—C8	−91.1 (5)
O2—C11—C12—C13	176.0 (4)	C5—C6—N1—C8	87.7 (4)
C11—C12—C13—C14	−2.2 (7)	C1—C6—N1—C7	85.1 (4)
C12—C13—C14—C15	2.5 (8)	C5—C6—N1—C7	−96.1 (4)
C13—C14—C15—C16	−1.8 (9)	O2—C8—N2—C9	178.6 (3)
C14—C15—C16—C11	0.8 (8)	N1—C8—N2—C9	−0.5 (5)
C14—C15—C16—C17	−178.8 (5)	C10—C9—N2—C8	0.7 (5)
C12—C11—C16—C15	−0.7 (6)	C19—C9—N2—C8	−178.7 (3)
O2—C11—C16—C15	−175.5 (4)	N2—C8—O2—C11	−3.0 (5)
C12—C11—C16—C17	179.0 (4)	N1—C8—O2—C11	176.3 (3)
O2—C11—C16—C17	4.2 (6)	C12—C11—O2—C8	74.9 (4)
S1—C18—C19—C9	−179.3 (2)	C16—C11—O2—C8	−110.0 (4)
S2—C18—C19—C9	0.7 (4)	O4—C22—O5—C23	−1.3 (5)
S1—C18—C19—C20	1.4 (4)	C21—C22—O5—C23	177.8 (3)
S2—C18—C19—C20	−178.6 (2)	C24—C23—O5—C22	−174.7 (4)
N2—C9—C19—C18	178.7 (3)	C19—C18—S1—C21	−1.0 (3)
C10—C9—C19—C18	−0.7 (4)	S2—C18—S1—C21	178.9 (3)
N2—C9—C19—C20	−2.3 (6)	C20—C21—S1—C18	0.4 (3)
C10—C9—C19—C20	178.3 (4)	C22—C21—S1—C18	179.9 (3)
C18—C19—C20—N3	179.2 (3)	C19—C18—S2—C10	−0.4 (3)
C9—C19—C20—N3	0.3 (6)	S1—C18—S2—C10	179.6 (3)
C18—C19—C20—C21	−1.1 (4)	C9—C10—S2—C18	0.0 (3)
C9—C19—C20—C21	179.9 (4)	C7—C10—S2—C18	−178.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5	0.86	2.22	2.799 (4)	124
N3—H3B···N2	0.86	2.56	3.158 (4)	128

Experimental details

Crystal data
Chemical formula	C₂₄H₁₉N₃O₄S₂
M_r	477.54
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	7.0996 (6), 10.444 (9), 16.9985 (13)
α, β, γ (°)	104.447 (1), 97.120 (1), 106.041 (1)
V (Å³)	1147.5 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.924, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	9743, 3980, 2644
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.179, 1.04
No. of reflections	3980
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.32

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