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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032940/wn6376sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032940/wn6376Isup2.hkl
Contains datablock I

CCDC reference: 289924

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 top

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 top
Crystal data top
C19H17N3O3SF(000) = 1536.00
Mr = 367.42Dx = 1.359 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ac 2abCell parameters from 30626 reflections
a = 9.3750 (1) Åθ = 2.2–27.5°
b = 14.4845 (2) ŵ = 0.20 mm1
c = 26.4390 (3) ÅT = 295 K
V = 3590.21 (7) Å3Block, colourless
Z = 80.31 × 0.20 × 0.14 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2299 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.041
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1112
Tmin = 0.868, Tmax = 0.972k = 1818
31250 measured reflectionsl = 3434
4111 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0002Fo2 + 0.9σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.033(Δ/σ)max < 0.001
wR(F2) = 0.072Δρmax = 0.47 e Å3
S = 1.01Δρmin = 0.38 e Å3
4111 reflectionsExtinction correction: Larson (1970), equation 22
236 parametersExtinction coefficient: 131 (16)
H-atom parameters constrained
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.15284 (4)0.48983 (3)0.38708 (2)0.0517 (1)
O10.6597 (1)0.46705 (8)0.44548 (5)0.0644 (4)
O20.3171 (1)0.24544 (8)0.49418 (5)0.0614 (4)
O30.0270 (1)0.49120 (8)0.28236 (4)0.0528 (3)
N10.4258 (1)0.47995 (8)0.41966 (5)0.0448 (4)
N20.2573 (1)0.36644 (9)0.44649 (5)0.0473 (4)
N30.2202 (1)0.47049 (9)0.23179 (5)0.0449 (4)
C10.2968 (1)0.4420 (1)0.42180 (6)0.0419 (5)
C20.5251 (2)0.4348 (1)0.44528 (6)0.0467 (5)
C30.5006 (2)0.3543 (1)0.47204 (6)0.0478 (5)
C40.3628 (2)0.3230 (1)0.47114 (6)0.0469 (5)
C50.6909 (2)0.5462 (1)0.41473 (8)0.0690 (6)
C60.4226 (2)0.1867 (1)0.51640 (8)0.0786 (7)
C70.2359 (1)0.5800 (1)0.35246 (6)0.0389 (4)
C80.3041 (2)0.6517 (1)0.37777 (7)0.0477 (5)
C90.3732 (2)0.7204 (1)0.35164 (8)0.0528 (6)
C100.3758 (2)0.7188 (1)0.29992 (8)0.0599 (6)
C110.3061 (2)0.6492 (1)0.27401 (7)0.0514 (5)
C120.2343 (1)0.5802 (1)0.29959 (6)0.0385 (4)
C130.1503 (1)0.5097 (1)0.27057 (6)0.0389 (4)
C140.1733 (1)0.3973 (1)0.20043 (6)0.0405 (5)
C150.2759 (2)0.3453 (1)0.17632 (7)0.0575 (6)
C160.2375 (2)0.2710 (1)0.14685 (8)0.0714 (7)
C170.0974 (2)0.2476 (1)0.14104 (7)0.0639 (6)
C180.0046 (2)0.2998 (1)0.16386 (7)0.0637 (6)
C190.0313 (2)0.3755 (1)0.19305 (7)0.0558 (5)
H3010.30320.49260.22510.054*
H30.57660.32200.49040.057*
H510.63910.54200.38350.083*
H520.79140.54840.40770.084*
H160.31150.23440.13000.086*
H610.48530.22250.53740.095*
H620.47680.15770.49000.095*
H80.30230.65310.41480.058*
H90.42080.77030.37010.063*
H100.42750.76660.28120.072*
H110.30660.64910.23690.062*
H150.37680.36180.18010.069*
H170.07020.19410.12060.077*
H180.10540.28370.15950.076*
H190.04350.41340.20860.067*
H630.37650.14040.53660.095*
H530.66300.60120.43240.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0402 (2)0.0621 (3)0.0528 (3)0.0065 (2)0.0064 (2)0.0151 (2)
O10.0408 (6)0.0599 (8)0.093 (1)0.0086 (6)0.0070 (7)0.0200 (7)
O20.0543 (7)0.0622 (8)0.0679 (9)0.0101 (6)0.0089 (7)0.0284 (7)
O30.0268 (5)0.0788 (8)0.0529 (7)0.0064 (6)0.0006 (5)0.0063 (6)
N10.0404 (7)0.0466 (8)0.0474 (9)0.0017 (6)0.0010 (7)0.0064 (7)
N20.0428 (7)0.0551 (9)0.0439 (8)0.0055 (7)0.0029 (7)0.0102 (7)
N30.0282 (6)0.0574 (9)0.0490 (9)0.0068 (6)0.0014 (6)0.0047 (7)
C10.0419 (9)0.048 (1)0.036 (1)0.0010 (8)0.0014 (7)0.0026 (8)
C20.0403 (9)0.049 (1)0.051 (1)0.0029 (8)0.0006 (9)0.0007 (9)
C30.0422 (9)0.051 (1)0.050 (1)0.0005 (8)0.0068 (8)0.0090 (9)
C40.051 (1)0.050 (1)0.040 (1)0.0072 (9)0.0015 (8)0.0095 (9)
C50.058 (1)0.059 (1)0.091 (2)0.015 (1)0.007 (1)0.013 (1)
C60.071 (1)0.074 (1)0.091 (2)0.003 (1)0.011 (1)0.040 (1)
C70.0319 (8)0.0396 (9)0.045 (1)0.0023 (7)0.0034 (8)0.0042 (8)
C80.0473 (9)0.046 (1)0.050 (1)0.0073 (8)0.0078 (9)0.0034 (9)
C90.047 (1)0.041 (1)0.071 (1)0.0018 (8)0.013 (1)0.002 (1)
C100.057 (1)0.050 (1)0.073 (1)0.0123 (9)0.004 (1)0.014 (1)
C110.0488 (9)0.056 (1)0.049 (1)0.0083 (9)0.0017 (9)0.0075 (9)
C120.0278 (8)0.0425 (9)0.045 (1)0.0026 (7)0.0021 (7)0.0020 (8)
C130.0303 (8)0.047 (1)0.0397 (9)0.0008 (8)0.0046 (7)0.0071 (8)
C140.0342 (8)0.047 (1)0.040 (1)0.0032 (8)0.0029 (8)0.0021 (8)
C150.0394 (9)0.063 (1)0.071 (1)0.0036 (9)0.000 (1)0.012 (1)
C160.059 (1)0.069 (1)0.087 (2)0.004 (1)0.000 (1)0.023 (1)
C170.066 (1)0.061 (1)0.064 (1)0.009 (1)0.010 (1)0.012 (1)
C180.047 (1)0.084 (1)0.060 (1)0.018 (1)0.010 (1)0.009 (1)
C190.0344 (8)0.079 (1)0.054 (1)0.0027 (9)0.0029 (8)0.012 (1)
Geometric parameters (Å, º) top
S1—C11.773 (2)C14—C191.382 (2)
S1—C71.775 (2)C15—C161.377 (3)
O1—C21.345 (2)C16—C171.365 (3)
O1—C51.435 (2)C17—C181.360 (3)
O2—C41.347 (2)C18—C191.382 (3)
O2—C61.431 (2)N3—H3010.8601
O3—C131.227 (2)C3—H30.9800
N1—C11.330 (2)C5—H510.9599
N1—C21.324 (2)C5—H520.9600
N2—C11.327 (2)C5—H530.9600
N2—C41.341 (2)C6—H610.9600
N3—C131.343 (2)C6—H620.9600
N3—C141.416 (2)C6—H630.9599
C2—C31.384 (2)C8—H80.9799
C3—C41.369 (2)C9—H90.9800
C7—C81.390 (2)C10—H100.9799
C7—C121.398 (2)C11—H110.9801
C8—C91.374 (2)C15—H150.9800
C9—C101.368 (3)C16—H160.9800
C10—C111.382 (2)C17—H170.9800
C11—C121.383 (2)C18—H180.9800
C12—C131.500 (2)C19—H190.9800
C14—C151.377 (2)
S1···O33.010 (1)C6···H533.4522
S1···N12.704 (1)C7···H82.0558
S1···N22.573 (1)C7···H93.2891
S1···C82.751 (2)C7···H113.2815
S1···C122.765 (2)C7···H173.3867
S1···C133.094 (2)C7···H183.2094
O1···N12.304 (2)C7···H193.5659
O1···C13.478 (2)C8···H513.5224
O1···C32.321 (2)C8···H613.5008
O1···C43.545 (2)C8···H92.0476
O1···C63.471 (2)C8···H103.2610
O2···N22.231 (2)C8···H173.5628
O2···C13.436 (2)C8···H182.8463
O2···C32.405 (2)C9···H163.0020
O2···C33.419 (2)C9···H613.3252
O2···C83.551 (2)C9···H82.0448
O3···N32.271 (2)C9···H102.0445
O3···N32.916 (1)C9···H113.2638
O3···C72.988 (2)C9···H153.2241
O3···C113.484 (2)C9···H182.6900
O3···C113.427 (2)C10···H163.4747
O3···C122.376 (2)C10···H83.2570
O3···C142.903 (2)C10···H92.0436
O3···C153.346 (2)C10···H112.0525
O3···C192.895 (2)C10···H153.1543
N1···N22.388 (2)C10···H182.9095
N1···C32.392 (2)C11···H3012.6115
N1···C42.715 (2)C11···H93.2685
N1···C52.667 (2)C11···H102.0538
N1···C72.904 (2)C11···H183.2294
N1···C82.952 (2)C12···H3012.4301
N1···C183.480 (2)C12···H83.2870
N1···C193.485 (2)C12···H103.2876
N2···C22.699 (2)C12···H112.0493
N2···C32.385 (2)C12···H183.3653
N2···C63.549 (2)C12···H193.1977
N2···C63.376 (2)C13···H3011.8872
N2···C93.502 (2)C13···H3013.2660
N3···O32.916 (1)C13···H112.6478
N3···C73.566 (2)C13···H153.5875
N3···C112.932 (2)C13···H192.8167
N3···C122.399 (2)C13···H193.2394
N3···C152.389 (2)C14···H3011.9527
N3···C192.465 (2)C14···H513.0697
C1···C22.231 (2)C14···H163.2724
C1···C32.651 (2)C14···H103.0052
C1···C42.249 (2)C14···H152.0469
C1···C72.772 (2)C14···H183.2715
C1···C83.253 (2)C14···H192.0573
C1···C183.583 (2)C14···H193.5899
C2···C23.487 (2)C15···H3012.5055
C2···C42.326 (2)C15···H513.5018
C2···C52.381 (2)C15···H162.0474
C2···C183.497 (2)C15···H93.2816
C3···O23.419 (2)C15···H103.5523
C3···C62.793 (3)C15···H103.2093
C3···C173.485 (2)C15···H113.3541
C4···C53.599 (3)C15···H173.2701
C4···C62.375 (3)C15···H193.2657
C5···C43.599 (3)C16···H523.5430
C6···O13.471 (2)C16···H93.2342
C6···N23.376 (2)C16···H112.9940
C7···C92.406 (2)C16···H152.0510
C7···C102.773 (2)C16···H172.0455
C7···C112.396 (2)C16···H183.2369
C7···C132.523 (2)C16···H633.4421
C8···O23.551 (2)C16···H533.3635
C8···C102.374 (3)C17···H523.3285
C8···C112.744 (3)C17···H162.0369
C8···C122.403 (2)C17···H113.0457
C9···N23.502 (2)C17···H153.2646
C9···C112.381 (3)C17···H182.0313
C9···C122.777 (2)C17···H193.2707
C10···C122.406 (2)C18···H163.2372
C11···O33.427 (2)C18···H103.2205
C11···C132.495 (2)C18···H113.4564
C13···C142.478 (2)C18···H172.0372
C13···C193.037 (2)C18···H192.0581
C14···C162.390 (3)C19···H3013.1764
C14···C172.769 (2)C19···H3013.4836
C14···C182.389 (2)C19···H513.3063
C15···O33.346 (2)C19···H102.8401
C15···C172.382 (3)C19···H153.2629
C15···C182.731 (2)C19···H173.2735
C15···C192.376 (2)C19···H182.0485
C16···C182.351 (3)H301···O32.1077
C16···C192.743 (3)H301···C133.2660
C17···C33.485 (2)H301···C193.4836
C17···C192.389 (3)H3···O22.4913
C18···N13.480 (2)H3···C43.5563
C18···C13.583 (2)H3···C63.2519
C18···C23.497 (2)H51···N33.3082
C19···N13.485 (2)H51···C143.0697
S1···H523.5360H51···C153.5018
S1···H82.8451H51···C193.3063
S1···H93.2848H52···S13.5360
O1···H32.5356H52···C163.5430
O1···H511.9751H52···C173.3285
O1···H521.9766H16···C52.9718
O1···H632.6032H16···C63.3794
O1···H531.9735H16···C93.0020
O2···H32.6753H16···C103.4747
O2···H32.4913H61···O23.2539
O2···H611.9747H61···N22.8896
O2···H613.2539H61···C83.5008
O2···H621.9669H61···C93.3252
O2···H623.5103H62···O23.5103
O2···H82.7281H62···N23.1404
O2···H631.9706H8···O22.7281
O2···H532.9558H8···N23.2497
O3···H3012.9996H8···C33.5180
O3···H3012.1077H8···C43.2655
O3···H103.2816H8···C63.4489
O3···H113.1237H9···S13.2848
O3···H152.5460H9···N22.9683
O3···H192.3475H9···C13.4955
N1···H33.2748H9···C63.3985
N1···H512.3912H9···C153.2816
N1···H523.5813H9···C163.2342
N1···H82.7658H10···O33.2816
N1···H183.5417H10···N33.5130
N1···H193.5373H10···C143.0052
N1···H532.8535H10···C153.5523
N2···H33.2734H10···C153.2093
N2···H612.8896H10···C183.2205
N2···H623.1404H10···C192.8401
N2···H83.2497H11···O33.1237
N2···H92.9683H11···C153.3541
N2···H183.3083H11···C162.9940
N2···H633.5995H11···C173.0457
N2···H533.3207H11···C183.4564
N3···H513.3082H15···O32.5460
N3···H103.5130H15···C93.2241
N3···H112.7141H15···C103.1543
N3···H152.5498H15···C133.5875
N3···H192.6775H17···C33.4361
N3···H192.8424H17···C53.2360
C1···H83.0640H17···C73.3867
C1···H93.4955H17···C83.5628
C1···H183.2737H18···N13.5417
C2···H32.0794H18···N23.3083
C2···H512.4934H18···C13.2737
C2···H523.1495H18···C43.5131
C2···H633.5026H18···C73.2094
C2···H532.7553H18···C82.8463
C3···H612.5774H18···C92.6900
C3···H622.8949H18···C102.9095
C3···H83.5180H18···C113.2294
C3···H173.4361H18···C123.3653
C3···H633.5328H19···N13.5373
C3···H533.0247H19···N32.8424
C4···H32.0673H19···C73.5659
C4···H33.5563H19···C123.1977
C4···H612.5492H19···C133.2394
C4···H622.6681H19···C143.5899
C4···H83.2655H63···O12.6032
C4···H183.5131H63···N23.5995
C4···H633.1629H63···C23.5026
C4···H532.7871H63···C33.5328
C5···H162.9718H63···C53.4622
C5···H173.2360H63···C163.4421
C5···H633.4622H53···O22.9558
C6···H32.5295H53···N23.3207
C6···H33.2519H53···C33.0247
C6···H163.3794H53···C42.7871
C6···H83.4489H53···C63.4522
C6···H93.3985H53···C163.3635
S1—C1—N1120.6 (1)C17—C18—C19121.2 (2)
S1—C1—N2111.4 (1)O1—C5—H51109.4764
C7—S1—C1102.76 (7)O1—C5—H52109.6027
S1—C7—C8120.2 (1)O1—C5—H53109.3364
S1—C7—C12120.8 (1)O2—C6—H61109.7555
O1—C2—N1119.4 (1)O2—C6—H62109.0758
O1—C2—C3116.5 (1)O2—C6—H63109.4011
C5—O1—C2117.8 (1)H301—N3—C13116.1613
O2—C4—N2112.1 (1)H301—N3—C14116.0292
O2—C4—C3124.6 (1)C2—C3—H3122.2459
C6—O2—C4117.5 (1)H3—C3—C4122.4441
O3—C13—C12120.9 (1)H52—C5—H51109.4748
O3—C13—N3124.1 (1)H53—C5—H51109.4656
N1—C1—N2128.0 (1)H53—C5—H52109.4714
C2—N1—C1114.5 (1)H62—C6—H61109.4718
N1—C2—C3124.1 (1)H63—C6—H61109.4469
C4—N2—C1114.9 (1)H63—C6—H62109.6762
N2—C4—C3123.2 (1)C7—C8—H8119.2932
N3—C13—C12115.0 (1)H8—C8—C9119.6836
C14—N3—C13127.8 (1)C8—C9—H9119.9612
N3—C14—C19123.5 (1)H9—C9—C10120.1088
N3—C14—C15117.6 (1)C9—C10—H10120.2119
C2—C3—C4115.3 (1)C10—C11—H11119.6805
C12—C7—C8119.0 (1)H10—C10—C11119.8328
C7—C8—C9121.0 (2)H11—C11—C12119.3158
C7—C12—C13121.1 (1)C14—C15—H15119.5766
C7—C12—C11119.0 (1)C14—C19—H19120.1639
C8—C9—C10119.9 (2)H15—C15—C16120.0066
C9—C10—C11120.0 (2)C15—C16—H16119.6567
C10—C11—C12121.0 (2)H16—C16—C17119.7239
C11—C12—C13119.8 (1)C16—C17—H17120.5962
C19—C14—C15118.9 (2)C17—C18—H18119.5601
C14—C15—C16120.4 (2)H17—C17—C18120.1470
C14—C19—C18119.6 (2)C18—C19—H19120.2401
C15—C16—C17120.6 (2)H18—C18—C19119.2788
C16—C17—C18119.3 (2)
C7—S1—C1—N14.2 (1)C2—C3—C4—N20.3 (2)
C7—S1—C1—N2173.6 (1)S1—C7—C8—C9177.7 (1)
C1—S1—C7—C860.2 (1)S1—C7—C12—C11176.9 (1)
C5—O1—C2—N14.2 (2)C7—C8—C9—C100.1 (2)
C6—O2—C4—N2172.3 (1)C8—C9—C10—C111.5 (2)
C6—O2—C4—C37.2 (2)C9—C10—C11—C120.6 (2)
C2—N1—C1—S1176.8 (1)C10—C11—C12—C71.6 (2)
C2—N1—C1—N20.7 (2)C7—C12—C13—O346.1 (2)
C1—N1—C2—O1179.7 (1)C7—C12—C13—N3134.1 (1)
C4—N2—C1—S1176.0 (1)C11—C12—C13—O3130.8 (2)
C4—N2—C1—N11.6 (2)C11—C12—C13—N349.1 (2)
C1—N2—C4—O2178.2 (1)N3—C14—C15—C16177.5 (2)
C1—N2—C4—C31.3 (2)N3—C14—C19—C18176.6 (2)
C14—N3—C13—O35.7 (2)C14—C15—C16—C170.0 (2)
C14—N3—C13—C12174.5 (1)C15—C16—C17—C181.4 (3)
C13—N3—C14—C15156.3 (2)C16—C17—C18—C190.5 (3)
O1—C2—C3—C4179.9 (1)C17—C18—C19—C141.8 (3)
C2—C3—C4—O2179.2 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H301···O3i0.862.112.916 (1)156
Symmetry code: (i) x+1/2, y, z+1/2.
 

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