2-(4,6-Dimethoxy­pyrimidin-2-ylsulfan­yl)-N-phenyl­benzamide

The title compound, C₁₉H₁₇N₃O₃S, was synthesized via the reaction of 2-(4,6-dimethoxy­pyrimidin-2-ylsulfan­yl)benzoic acid and aniline in dichloro­methane using dicyclo­hexyl­carbodiimide as catalyst. The dihedral angles between the pyrimidine plane and the planes of the two benzene rings are 71.2 (2) and 62.7 (2)°; the dihedral angle between the planes of the two benzene rings is 68.4 (4)°. The conformation of the compound is U-shaped.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.033
• wR factor = 0.072
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

2-(4,6-Dimethoxypyrimidin-2-ylsulfanyl)-N-phenylbenzamide

Crystal data

C19H17N3O3S	F(000) = 1536.00
Mr = 367.42	Dx = 1.359 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 30626 reflections
a = 9.3750 (1) Å	θ = 2.2–27.5°
b = 14.4845 (2) Å	µ = 0.20 mm^−1
c = 26.4390 (3) Å	T = 295 K
V = 3590.21 (7) Å^3	Block, colourless
Z = 8	0.31 × 0.20 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2299 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.041
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→12
Tmin = 0.868, Tmax = 0.972	k = −18→18
31250 measured reflections	l = −34→34
4111 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0002Fo^2 + 0.9σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.033	(Δ/σ)max < 0.001
wR(F^2) = 0.072	Δρmax = 0.47 e Å^−3
S = 1.01	Δρmin = −0.38 e Å^−3
4111 reflections	Extinction correction: Larson (1970), equation 22
236 parameters	Extinction coefficient: 131 (16)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.15284 (4)	0.48983 (3)	0.38708 (2)	0.0517 (1)
O1	0.6597 (1)	0.46705 (8)	0.44548 (5)	0.0644 (4)
O2	0.3171 (1)	0.24544 (8)	0.49418 (5)	0.0614 (4)
O3	0.0270 (1)	0.49120 (8)	0.28236 (4)	0.0528 (3)
N1	0.4258 (1)	0.47995 (8)	0.41966 (5)	0.0448 (4)
N2	0.2573 (1)	0.36644 (9)	0.44649 (5)	0.0473 (4)
N3	0.2202 (1)	0.47049 (9)	0.23179 (5)	0.0449 (4)
C1	0.2968 (1)	0.4420 (1)	0.42180 (6)	0.0419 (5)
C2	0.5251 (2)	0.4348 (1)	0.44528 (6)	0.0467 (5)
C3	0.5006 (2)	0.3543 (1)	0.47204 (6)	0.0478 (5)
C4	0.3628 (2)	0.3230 (1)	0.47114 (6)	0.0469 (5)
C5	0.6909 (2)	0.5462 (1)	0.41473 (8)	0.0690 (6)
C6	0.4226 (2)	0.1867 (1)	0.51640 (8)	0.0786 (7)
C7	0.2359 (1)	0.5800 (1)	0.35246 (6)	0.0389 (4)
C8	0.3041 (2)	0.6517 (1)	0.37777 (7)	0.0477 (5)
C9	0.3732 (2)	0.7204 (1)	0.35164 (8)	0.0528 (6)
C10	0.3758 (2)	0.7188 (1)	0.29992 (8)	0.0599 (6)
C11	0.3061 (2)	0.6492 (1)	0.27401 (7)	0.0514 (5)
C12	0.2343 (1)	0.5802 (1)	0.29959 (6)	0.0385 (4)
C13	0.1503 (1)	0.5097 (1)	0.27057 (6)	0.0389 (4)
C14	0.1733 (1)	0.3973 (1)	0.20043 (6)	0.0405 (5)
C15	0.2759 (2)	0.3453 (1)	0.17632 (7)	0.0575 (6)
C16	0.2375 (2)	0.2710 (1)	0.14685 (8)	0.0714 (7)
C17	0.0974 (2)	0.2476 (1)	0.14104 (7)	0.0639 (6)
C18	−0.0046 (2)	0.2998 (1)	0.16386 (7)	0.0637 (6)
C19	0.0313 (2)	0.3755 (1)	0.19305 (7)	0.0558 (5)
H301	0.3032	0.4926	0.2251	0.054*
H3	0.5766	0.3220	0.4904	0.057*
H51	0.6391	0.5420	0.3835	0.083*
H52	0.7914	0.5484	0.4077	0.084*
H16	0.3115	0.2344	0.1300	0.086*
H61	0.4853	0.2225	0.5374	0.095*
H62	0.4768	0.1577	0.4900	0.095*
H8	0.3023	0.6531	0.4148	0.058*
H9	0.4208	0.7703	0.3701	0.063*
H10	0.4275	0.7666	0.2812	0.072*
H11	0.3066	0.6491	0.2369	0.062*
H15	0.3768	0.3618	0.1801	0.069*
H17	0.0702	0.1941	0.1206	0.077*
H18	−0.1054	0.2837	0.1595	0.076*
H19	−0.0435	0.4134	0.2086	0.067*
H63	0.3765	0.1404	0.5366	0.095*
H53	0.6630	0.6012	0.4324	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0402 (2)	0.0621 (3)	0.0528 (3)	−0.0065 (2)	−0.0064 (2)	0.0151 (2)
O1	0.0408 (6)	0.0599 (8)	0.093 (1)	−0.0086 (6)	−0.0070 (7)	0.0200 (7)
O2	0.0543 (7)	0.0622 (8)	0.0679 (9)	−0.0101 (6)	−0.0089 (7)	0.0284 (7)
O3	0.0268 (5)	0.0788 (8)	0.0529 (7)	−0.0064 (6)	0.0006 (5)	−0.0063 (6)
N1	0.0404 (7)	0.0466 (8)	0.0474 (9)	−0.0017 (6)	−0.0010 (7)	0.0064 (7)
N2	0.0428 (7)	0.0551 (9)	0.0439 (8)	−0.0055 (7)	−0.0029 (7)	0.0102 (7)
N3	0.0282 (6)	0.0574 (9)	0.0490 (9)	−0.0068 (6)	0.0014 (6)	−0.0047 (7)
C1	0.0419 (9)	0.048 (1)	0.036 (1)	−0.0010 (8)	−0.0014 (7)	0.0026 (8)
C2	0.0403 (9)	0.049 (1)	0.051 (1)	−0.0029 (8)	−0.0006 (9)	0.0007 (9)
C3	0.0422 (9)	0.051 (1)	0.050 (1)	0.0005 (8)	−0.0068 (8)	0.0090 (9)
C4	0.051 (1)	0.050 (1)	0.040 (1)	−0.0072 (9)	−0.0015 (8)	0.0095 (9)
C5	0.058 (1)	0.059 (1)	0.091 (2)	−0.015 (1)	0.007 (1)	0.013 (1)
C6	0.071 (1)	0.074 (1)	0.091 (2)	−0.003 (1)	−0.011 (1)	0.040 (1)
C7	0.0319 (8)	0.0396 (9)	0.045 (1)	0.0023 (7)	−0.0034 (8)	0.0042 (8)
C8	0.0473 (9)	0.046 (1)	0.050 (1)	0.0073 (8)	−0.0078 (9)	−0.0034 (9)
C9	0.047 (1)	0.041 (1)	0.071 (1)	−0.0018 (8)	−0.013 (1)	−0.002 (1)
C10	0.057 (1)	0.050 (1)	0.073 (1)	−0.0123 (9)	−0.004 (1)	0.014 (1)
C11	0.0488 (9)	0.056 (1)	0.049 (1)	−0.0083 (9)	−0.0017 (9)	0.0075 (9)
C12	0.0278 (8)	0.0425 (9)	0.045 (1)	0.0026 (7)	−0.0021 (7)	0.0020 (8)
C13	0.0303 (8)	0.047 (1)	0.0397 (9)	0.0008 (8)	−0.0046 (7)	0.0071 (8)
C14	0.0342 (8)	0.047 (1)	0.040 (1)	−0.0032 (8)	−0.0029 (8)	0.0021 (8)
C15	0.0394 (9)	0.063 (1)	0.071 (1)	−0.0036 (9)	−0.000 (1)	−0.012 (1)
C16	0.059 (1)	0.069 (1)	0.087 (2)	0.004 (1)	0.000 (1)	−0.023 (1)
C17	0.066 (1)	0.061 (1)	0.064 (1)	−0.009 (1)	−0.010 (1)	−0.012 (1)
C18	0.047 (1)	0.084 (1)	0.060 (1)	−0.018 (1)	−0.010 (1)	−0.009 (1)
C19	0.0344 (8)	0.079 (1)	0.054 (1)	−0.0027 (9)	−0.0029 (8)	−0.012 (1)

Geometric parameters (Å, º)

S1—C1	1.773 (2)	C14—C19	1.382 (2)
S1—C7	1.775 (2)	C15—C16	1.377 (3)
O1—C2	1.345 (2)	C16—C17	1.365 (3)
O1—C5	1.435 (2)	C17—C18	1.360 (3)
O2—C4	1.347 (2)	C18—C19	1.382 (3)
O2—C6	1.431 (2)	N3—H301	0.8601
O3—C13	1.227 (2)	C3—H3	0.9800
N1—C1	1.330 (2)	C5—H51	0.9599
N1—C2	1.324 (2)	C5—H52	0.9600
N2—C1	1.327 (2)	C5—H53	0.9600
N2—C4	1.341 (2)	C6—H61	0.9600
N3—C13	1.343 (2)	C6—H62	0.9600
N3—C14	1.416 (2)	C6—H63	0.9599
C2—C3	1.384 (2)	C8—H8	0.9799
C3—C4	1.369 (2)	C9—H9	0.9800
C7—C8	1.390 (2)	C10—H10	0.9799
C7—C12	1.398 (2)	C11—H11	0.9801
C8—C9	1.374 (2)	C15—H15	0.9800
C9—C10	1.368 (3)	C16—H16	0.9800
C10—C11	1.382 (2)	C17—H17	0.9800
C11—C12	1.383 (2)	C18—H18	0.9800
C12—C13	1.500 (2)	C19—H19	0.9800
C14—C15	1.377 (2)
S1···O3	3.010 (1)	C6···H53	3.4522
S1···N1	2.704 (1)	C7···H8	2.0558
S1···N2	2.573 (1)	C7···H9	3.2891
S1···C8	2.751 (2)	C7···H11	3.2815
S1···C12	2.765 (2)	C7···H17	3.3867
S1···C13	3.094 (2)	C7···H18	3.2094
O1···N1	2.304 (2)	C7···H19	3.5659
O1···C1	3.478 (2)	C8···H51	3.5224
O1···C3	2.321 (2)	C8···H61	3.5008
O1···C4	3.545 (2)	C8···H9	2.0476
O1···C6	3.471 (2)	C8···H10	3.2610
O2···N2	2.231 (2)	C8···H17	3.5628
O2···C1	3.436 (2)	C8···H18	2.8463
O2···C3	2.405 (2)	C9···H16	3.0020
O2···C3	3.419 (2)	C9···H61	3.3252
O2···C8	3.551 (2)	C9···H8	2.0448
O3···N3	2.271 (2)	C9···H10	2.0445
O3···N3	2.916 (1)	C9···H11	3.2638
O3···C7	2.988 (2)	C9···H15	3.2241
O3···C11	3.484 (2)	C9···H18	2.6900
O3···C11	3.427 (2)	C10···H16	3.4747
O3···C12	2.376 (2)	C10···H8	3.2570
O3···C14	2.903 (2)	C10···H9	2.0436
O3···C15	3.346 (2)	C10···H11	2.0525
O3···C19	2.895 (2)	C10···H15	3.1543
N1···N2	2.388 (2)	C10···H18	2.9095
N1···C3	2.392 (2)	C11···H301	2.6115
N1···C4	2.715 (2)	C11···H9	3.2685
N1···C5	2.667 (2)	C11···H10	2.0538
N1···C7	2.904 (2)	C11···H18	3.2294
N1···C8	2.952 (2)	C12···H301	2.4301
N1···C18	3.480 (2)	C12···H8	3.2870
N1···C19	3.485 (2)	C12···H10	3.2876
N2···C2	2.699 (2)	C12···H11	2.0493
N2···C3	2.385 (2)	C12···H18	3.3653
N2···C6	3.549 (2)	C12···H19	3.1977
N2···C6	3.376 (2)	C13···H301	1.8872
N2···C9	3.502 (2)	C13···H301	3.2660
N3···O3	2.916 (1)	C13···H11	2.6478
N3···C7	3.566 (2)	C13···H15	3.5875
N3···C11	2.932 (2)	C13···H19	2.8167
N3···C12	2.399 (2)	C13···H19	3.2394
N3···C15	2.389 (2)	C14···H301	1.9527
N3···C19	2.465 (2)	C14···H51	3.0697
C1···C2	2.231 (2)	C14···H16	3.2724
C1···C3	2.651 (2)	C14···H10	3.0052
C1···C4	2.249 (2)	C14···H15	2.0469
C1···C7	2.772 (2)	C14···H18	3.2715
C1···C8	3.253 (2)	C14···H19	2.0573
C1···C18	3.583 (2)	C14···H19	3.5899
C2···C2	3.487 (2)	C15···H301	2.5055
C2···C4	2.326 (2)	C15···H51	3.5018
C2···C5	2.381 (2)	C15···H16	2.0474
C2···C18	3.497 (2)	C15···H9	3.2816
C3···O2	3.419 (2)	C15···H10	3.5523
C3···C6	2.793 (3)	C15···H10	3.2093
C3···C17	3.485 (2)	C15···H11	3.3541
C4···C5	3.599 (3)	C15···H17	3.2701
C4···C6	2.375 (3)	C15···H19	3.2657
C5···C4	3.599 (3)	C16···H52	3.5430
C6···O1	3.471 (2)	C16···H9	3.2342
C6···N2	3.376 (2)	C16···H11	2.9940
C7···C9	2.406 (2)	C16···H15	2.0510
C7···C10	2.773 (2)	C16···H17	2.0455
C7···C11	2.396 (2)	C16···H18	3.2369
C7···C13	2.523 (2)	C16···H63	3.4421
C8···O2	3.551 (2)	C16···H53	3.3635
C8···C10	2.374 (3)	C17···H52	3.3285
C8···C11	2.744 (3)	C17···H16	2.0369
C8···C12	2.403 (2)	C17···H11	3.0457
C9···N2	3.502 (2)	C17···H15	3.2646
C9···C11	2.381 (3)	C17···H18	2.0313
C9···C12	2.777 (2)	C17···H19	3.2707
C10···C12	2.406 (2)	C18···H16	3.2372
C11···O3	3.427 (2)	C18···H10	3.2205
C11···C13	2.495 (2)	C18···H11	3.4564
C13···C14	2.478 (2)	C18···H17	2.0372
C13···C19	3.037 (2)	C18···H19	2.0581
C14···C16	2.390 (3)	C19···H301	3.1764
C14···C17	2.769 (2)	C19···H301	3.4836
C14···C18	2.389 (2)	C19···H51	3.3063
C15···O3	3.346 (2)	C19···H10	2.8401
C15···C17	2.382 (3)	C19···H15	3.2629
C15···C18	2.731 (2)	C19···H17	3.2735
C15···C19	2.376 (2)	C19···H18	2.0485
C16···C18	2.351 (3)	H301···O3	2.1077
C16···C19	2.743 (3)	H301···C13	3.2660
C17···C3	3.485 (2)	H301···C19	3.4836
C17···C19	2.389 (3)	H3···O2	2.4913
C18···N1	3.480 (2)	H3···C4	3.5563
C18···C1	3.583 (2)	H3···C6	3.2519
C18···C2	3.497 (2)	H51···N3	3.3082
C19···N1	3.485 (2)	H51···C14	3.0697
S1···H52	3.5360	H51···C15	3.5018
S1···H8	2.8451	H51···C19	3.3063
S1···H9	3.2848	H52···S1	3.5360
O1···H3	2.5356	H52···C16	3.5430
O1···H51	1.9751	H52···C17	3.3285
O1···H52	1.9766	H16···C5	2.9718
O1···H63	2.6032	H16···C6	3.3794
O1···H53	1.9735	H16···C9	3.0020
O2···H3	2.6753	H16···C10	3.4747
O2···H3	2.4913	H61···O2	3.2539
O2···H61	1.9747	H61···N2	2.8896
O2···H61	3.2539	H61···C8	3.5008
O2···H62	1.9669	H61···C9	3.3252
O2···H62	3.5103	H62···O2	3.5103
O2···H8	2.7281	H62···N2	3.1404
O2···H63	1.9706	H8···O2	2.7281
O2···H53	2.9558	H8···N2	3.2497
O3···H301	2.9996	H8···C3	3.5180
O3···H301	2.1077	H8···C4	3.2655
O3···H10	3.2816	H8···C6	3.4489
O3···H11	3.1237	H9···S1	3.2848
O3···H15	2.5460	H9···N2	2.9683
O3···H19	2.3475	H9···C1	3.4955
N1···H3	3.2748	H9···C6	3.3985
N1···H51	2.3912	H9···C15	3.2816
N1···H52	3.5813	H9···C16	3.2342
N1···H8	2.7658	H10···O3	3.2816
N1···H18	3.5417	H10···N3	3.5130
N1···H19	3.5373	H10···C14	3.0052
N1···H53	2.8535	H10···C15	3.5523
N2···H3	3.2734	H10···C15	3.2093
N2···H61	2.8896	H10···C18	3.2205
N2···H62	3.1404	H10···C19	2.8401
N2···H8	3.2497	H11···O3	3.1237
N2···H9	2.9683	H11···C15	3.3541
N2···H18	3.3083	H11···C16	2.9940
N2···H63	3.5995	H11···C17	3.0457
N2···H53	3.3207	H11···C18	3.4564
N3···H51	3.3082	H15···O3	2.5460
N3···H10	3.5130	H15···C9	3.2241
N3···H11	2.7141	H15···C10	3.1543
N3···H15	2.5498	H15···C13	3.5875
N3···H19	2.6775	H17···C3	3.4361
N3···H19	2.8424	H17···C5	3.2360
C1···H8	3.0640	H17···C7	3.3867
C1···H9	3.4955	H17···C8	3.5628
C1···H18	3.2737	H18···N1	3.5417
C2···H3	2.0794	H18···N2	3.3083
C2···H51	2.4934	H18···C1	3.2737
C2···H52	3.1495	H18···C4	3.5131
C2···H63	3.5026	H18···C7	3.2094
C2···H53	2.7553	H18···C8	2.8463
C3···H61	2.5774	H18···C9	2.6900
C3···H62	2.8949	H18···C10	2.9095
C3···H8	3.5180	H18···C11	3.2294
C3···H17	3.4361	H18···C12	3.3653
C3···H63	3.5328	H19···N1	3.5373
C3···H53	3.0247	H19···N3	2.8424
C4···H3	2.0673	H19···C7	3.5659
C4···H3	3.5563	H19···C12	3.1977
C4···H61	2.5492	H19···C13	3.2394
C4···H62	2.6681	H19···C14	3.5899
C4···H8	3.2655	H63···O1	2.6032
C4···H18	3.5131	H63···N2	3.5995
C4···H63	3.1629	H63···C2	3.5026
C4···H53	2.7871	H63···C3	3.5328
C5···H16	2.9718	H63···C5	3.4622
C5···H17	3.2360	H63···C16	3.4421
C5···H63	3.4622	H53···O2	2.9558
C6···H3	2.5295	H53···N2	3.3207
C6···H3	3.2519	H53···C3	3.0247
C6···H16	3.3794	H53···C4	2.7871
C6···H8	3.4489	H53···C6	3.4522
C6···H9	3.3985	H53···C16	3.3635
S1—C1—N1	120.6 (1)	C17—C18—C19	121.2 (2)
S1—C1—N2	111.4 (1)	O1—C5—H51	109.4764
C7—S1—C1	102.76 (7)	O1—C5—H52	109.6027
S1—C7—C8	120.2 (1)	O1—C5—H53	109.3364
S1—C7—C12	120.8 (1)	O2—C6—H61	109.7555
O1—C2—N1	119.4 (1)	O2—C6—H62	109.0758
O1—C2—C3	116.5 (1)	O2—C6—H63	109.4011
C5—O1—C2	117.8 (1)	H301—N3—C13	116.1613
O2—C4—N2	112.1 (1)	H301—N3—C14	116.0292
O2—C4—C3	124.6 (1)	C2—C3—H3	122.2459
C6—O2—C4	117.5 (1)	H3—C3—C4	122.4441
O3—C13—C12	120.9 (1)	H52—C5—H51	109.4748
O3—C13—N3	124.1 (1)	H53—C5—H51	109.4656
N1—C1—N2	128.0 (1)	H53—C5—H52	109.4714
C2—N1—C1	114.5 (1)	H62—C6—H61	109.4718
N1—C2—C3	124.1 (1)	H63—C6—H61	109.4469
C4—N2—C1	114.9 (1)	H63—C6—H62	109.6762
N2—C4—C3	123.2 (1)	C7—C8—H8	119.2932
N3—C13—C12	115.0 (1)	H8—C8—C9	119.6836
C14—N3—C13	127.8 (1)	C8—C9—H9	119.9612
N3—C14—C19	123.5 (1)	H9—C9—C10	120.1088
N3—C14—C15	117.6 (1)	C9—C10—H10	120.2119
C2—C3—C4	115.3 (1)	C10—C11—H11	119.6805
C12—C7—C8	119.0 (1)	H10—C10—C11	119.8328
C7—C8—C9	121.0 (2)	H11—C11—C12	119.3158
C7—C12—C13	121.1 (1)	C14—C15—H15	119.5766
C7—C12—C11	119.0 (1)	C14—C19—H19	120.1639
C8—C9—C10	119.9 (2)	H15—C15—C16	120.0066
C9—C10—C11	120.0 (2)	C15—C16—H16	119.6567
C10—C11—C12	121.0 (2)	H16—C16—C17	119.7239
C11—C12—C13	119.8 (1)	C16—C17—H17	120.5962
C19—C14—C15	118.9 (2)	C17—C18—H18	119.5601
C14—C15—C16	120.4 (2)	H17—C17—C18	120.1470
C14—C19—C18	119.6 (2)	C18—C19—H19	120.2401
C15—C16—C17	120.6 (2)	H18—C18—C19	119.2788
C16—C17—C18	119.3 (2)
C7—S1—C1—N1	4.2 (1)	C2—C3—C4—N2	−0.3 (2)
C7—S1—C1—N2	−173.6 (1)	S1—C7—C8—C9	177.7 (1)
C1—S1—C7—C8	−60.2 (1)	S1—C7—C12—C11	−176.9 (1)
C5—O1—C2—N1	−4.2 (2)	C7—C8—C9—C10	−0.1 (2)
C6—O2—C4—N2	172.3 (1)	C8—C9—C10—C11	1.5 (2)
C6—O2—C4—C3	−7.2 (2)	C9—C10—C11—C12	−0.6 (2)
C2—N1—C1—S1	−176.8 (1)	C10—C11—C12—C7	−1.6 (2)
C2—N1—C1—N2	0.7 (2)	C7—C12—C13—O3	46.1 (2)
C1—N1—C2—O1	179.7 (1)	C7—C12—C13—N3	−134.1 (1)
C4—N2—C1—S1	176.0 (1)	C11—C12—C13—O3	−130.8 (2)
C4—N2—C1—N1	−1.6 (2)	C11—C12—C13—N3	49.1 (2)
C1—N2—C4—O2	−178.2 (1)	N3—C14—C15—C16	177.5 (2)
C1—N2—C4—C3	1.3 (2)	N3—C14—C19—C18	−176.6 (2)
C14—N3—C13—O3	−5.7 (2)	C14—C15—C16—C17	0.0 (2)
C14—N3—C13—C12	174.5 (1)	C15—C16—C17—C18	1.4 (3)
C13—N3—C14—C15	−156.3 (2)	C16—C17—C18—C19	−0.5 (3)
O1—C2—C3—C4	−179.9 (1)	C17—C18—C19—C14	−1.8 (3)
C2—C3—C4—O2	179.2 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H301···O3^i	0.86	2.11	2.916 (1)	156

Symmetry code: (i) x+1/2, y, −z+1/2.