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In the title compound, C20H19N3OS, the three fused rings of the benzo[4,5]thieno[3,2-d]pyrimidone system are essentially coplanar. The crystal packing is mainly stabilized by C—H...π and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048100/is2099sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048100/is2099Isup2.hkl
Contains datablock I

CCDC reference: 630024

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.054
  • wR factor = 0.149
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 - C18 .. 5.61 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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 (Bruker, 2001).

2-(tert-Butylamino)-3-phenyl-3H-benzo[4,5]thieno[3,2-e]pyrimidin-4-one top
Crystal data top
C20H19N3OSZ = 2
Mr = 349.44F(000) = 368
Triclinic, P1Dx = 1.306 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7106 (15) ÅCell parameters from 1055 reflections
b = 10.1139 (15) Åθ = 2.3–25.0°
c = 10.5568 (16) ŵ = 0.20 mm1
α = 104.928 (3)°T = 292 K
β = 115.988 (2)°Block, colourless
γ = 91.557 (3)°0.20 × 0.10 × 0.10 mm
V = 888.7 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3058 independent reflections
Radiation source: fine-focus sealed tube2179 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 119
Tmin = 0.962, Tmax = 0.981k = 1111
4495 measured reflectionsl = 1212
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0723P)2 + 0.077P]
where P = (Fo2 + 2Fc2)/3
3058 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.22 e Å3
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*/Ueq
C10.7806 (3)0.1215 (3)1.1700 (3)0.0436 (7)
C20.8745 (4)0.0945 (3)1.3019 (3)0.0519 (8)
H20.96960.06591.31910.062*
C30.8220 (4)0.1114 (3)1.4056 (3)0.0571 (9)
H30.88370.09391.49420.068*
C40.6811 (4)0.1533 (3)1.3835 (3)0.0561 (8)
H40.64900.16241.45590.067*
C50.5883 (4)0.1817 (3)1.2541 (3)0.0506 (8)
H50.49410.21151.23920.061*
C60.6376 (3)0.1651 (3)1.1454 (3)0.0390 (7)
C70.5593 (3)0.1870 (3)1.0031 (3)0.0374 (6)
C80.6435 (3)0.1597 (3)0.9263 (3)0.0394 (7)
C90.5906 (3)0.1828 (3)0.7852 (3)0.0421 (7)
C100.3683 (3)0.2556 (3)0.8253 (3)0.0392 (7)
C110.3844 (3)0.2634 (3)0.6002 (3)0.0429 (7)
C120.3274 (3)0.1578 (3)0.4709 (3)0.0482 (7)
H120.33130.06630.47200.058*
C130.2638 (4)0.1887 (4)0.3384 (3)0.0629 (10)
H130.22430.11750.24980.075*
C140.2586 (4)0.3230 (5)0.3369 (4)0.0685 (11)
H140.21450.34260.24720.082*
C150.3184 (4)0.4301 (4)0.4677 (4)0.0668 (10)
H150.31480.52160.46650.080*
C160.3835 (4)0.3999 (3)0.6001 (3)0.0544 (8)
H160.42660.47110.68890.065*
C170.1484 (3)0.3658 (3)0.8517 (3)0.0474 (8)
C180.2579 (4)0.4756 (3)0.9946 (4)0.0670 (10)
H18A0.32970.43211.06130.101*
H18B0.19910.52471.03890.101*
H18C0.31420.53950.97390.101*
C190.0709 (4)0.2560 (4)0.8828 (4)0.0650 (9)
H19A0.00830.19480.79150.098*
H19B0.02500.29920.94390.098*
H19C0.14670.20400.93310.098*
C200.0263 (4)0.4328 (4)0.7505 (4)0.0788 (12)
H20A0.07630.50940.73980.118*
H20B0.04100.46550.79250.118*
H20C0.03370.36580.65540.118*
N10.4199 (3)0.2336 (2)0.9536 (2)0.0435 (6)
N20.4472 (3)0.2328 (2)0.7398 (2)0.0387 (6)
N30.2324 (3)0.3025 (3)0.7688 (2)0.0483 (6)
H3A0.19040.29520.67620.058*
O10.6564 (2)0.1649 (2)0.7083 (2)0.0569 (6)
S10.81909 (9)0.10819 (9)1.02092 (8)0.0511 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0444 (17)0.0512 (18)0.0392 (16)0.0118 (14)0.0208 (13)0.0164 (14)
C20.0534 (19)0.056 (2)0.0472 (18)0.0157 (16)0.0187 (15)0.0232 (16)
C30.071 (2)0.059 (2)0.0421 (18)0.0151 (17)0.0221 (17)0.0237 (16)
C40.073 (2)0.063 (2)0.0490 (19)0.0175 (18)0.0368 (17)0.0266 (17)
C50.0551 (19)0.059 (2)0.0489 (18)0.0152 (16)0.0308 (16)0.0216 (16)
C60.0456 (17)0.0389 (16)0.0373 (15)0.0063 (13)0.0213 (13)0.0151 (13)
C70.0425 (16)0.0346 (15)0.0379 (15)0.0056 (12)0.0206 (13)0.0114 (12)
C80.0439 (17)0.0401 (16)0.0373 (15)0.0100 (13)0.0203 (13)0.0130 (13)
C90.0404 (16)0.0487 (18)0.0388 (16)0.0069 (13)0.0203 (14)0.0120 (13)
C100.0416 (16)0.0417 (17)0.0391 (15)0.0103 (13)0.0212 (13)0.0146 (13)
C110.0382 (16)0.060 (2)0.0379 (16)0.0113 (14)0.0204 (13)0.0210 (15)
C120.0499 (18)0.057 (2)0.0438 (17)0.0136 (15)0.0262 (15)0.0162 (15)
C130.053 (2)0.100 (3)0.0355 (17)0.0200 (19)0.0223 (16)0.0159 (18)
C140.063 (2)0.112 (3)0.055 (2)0.037 (2)0.0336 (19)0.049 (2)
C150.071 (2)0.079 (3)0.066 (2)0.025 (2)0.033 (2)0.042 (2)
C160.062 (2)0.055 (2)0.0499 (19)0.0110 (16)0.0250 (16)0.0224 (16)
C170.0453 (17)0.0555 (19)0.0427 (17)0.0169 (15)0.0227 (14)0.0115 (15)
C180.070 (2)0.058 (2)0.072 (2)0.0150 (18)0.037 (2)0.0092 (18)
C190.056 (2)0.069 (2)0.076 (2)0.0080 (18)0.0385 (19)0.0176 (19)
C200.079 (3)0.096 (3)0.074 (3)0.052 (2)0.037 (2)0.038 (2)
N10.0402 (14)0.0588 (16)0.0401 (13)0.0152 (12)0.0225 (11)0.0206 (12)
N20.0420 (14)0.0442 (14)0.0352 (12)0.0121 (11)0.0194 (11)0.0166 (11)
N30.0442 (14)0.0721 (18)0.0361 (13)0.0243 (13)0.0212 (11)0.0217 (13)
O10.0530 (13)0.0881 (17)0.0470 (12)0.0269 (12)0.0336 (11)0.0269 (12)
S10.0469 (5)0.0716 (6)0.0465 (5)0.0234 (4)0.0264 (4)0.0259 (4)
Geometric parameters (Å, º) top
C1—C21.393 (4)C12—C131.384 (4)
C1—C61.402 (4)C12—H120.9300
C1—S11.745 (3)C13—C141.364 (5)
C2—C31.372 (4)C13—H130.9300
C2—H20.9300C14—C151.382 (5)
C3—C41.382 (4)C14—H140.9300
C3—H30.9300C15—C161.380 (4)
C4—C51.377 (4)C15—H150.9300
C4—H40.9300C16—H160.9300
C5—C61.400 (4)C17—N31.485 (3)
C5—H50.9300C17—C191.506 (4)
C6—C71.437 (3)C17—C181.519 (4)
C7—N11.367 (3)C17—C201.521 (4)
C7—C81.371 (4)C18—H18A0.9600
C8—C91.433 (4)C18—H18B0.9600
C8—S11.732 (3)C18—H18C0.9600
C9—O11.219 (3)C19—H19A0.9600
C9—N21.415 (3)C19—H19B0.9600
C10—N11.304 (3)C19—H19C0.9600
C10—N31.346 (3)C20—H20A0.9600
C10—N21.400 (3)C20—H20B0.9600
C11—C121.366 (4)C20—H20C0.9600
C11—C161.381 (4)N3—H3A0.8600
C11—N21.448 (3)
C2—C1—C6120.6 (3)C13—C14—H14119.8
C2—C1—S1127.2 (2)C15—C14—H14119.8
C6—C1—S1112.20 (19)C16—C15—C14119.3 (3)
C3—C2—C1117.9 (3)C16—C15—H15120.3
C3—C2—H2121.1C14—C15—H15120.3
C1—C2—H2121.1C15—C16—C11119.7 (3)
C2—C3—C4122.6 (3)C15—C16—H16120.2
C2—C3—H3118.7C11—C16—H16120.2
C4—C3—H3118.7N3—C17—C19110.5 (3)
C5—C4—C3119.9 (3)N3—C17—C18110.8 (3)
C5—C4—H4120.0C19—C17—C18110.5 (3)
C3—C4—H4120.0N3—C17—C20105.4 (2)
C4—C5—C6119.1 (3)C19—C17—C20109.8 (3)
C4—C5—H5120.4C18—C17—C20109.7 (3)
C6—C5—H5120.4C17—C18—H18A109.5
C5—C6—C1119.8 (2)C17—C18—H18B109.5
C5—C6—C7128.4 (3)H18A—C18—H18B109.5
C1—C6—C7111.7 (2)C17—C18—H18C109.5
N1—C7—C8124.7 (2)H18A—C18—H18C109.5
N1—C7—C6123.5 (2)H18B—C18—H18C109.5
C8—C7—C6111.8 (2)C17—C19—H19A109.5
C7—C8—C9120.8 (3)C17—C19—H19B109.5
C7—C8—S1113.9 (2)H19A—C19—H19B109.5
C9—C8—S1125.1 (2)C17—C19—H19C109.5
O1—C9—N2120.9 (2)H19A—C19—H19C109.5
O1—C9—C8126.8 (3)H19B—C19—H19C109.5
N2—C9—C8112.3 (2)C17—C20—H20A109.5
N1—C10—N3119.9 (2)C17—C20—H20B109.5
N1—C10—N2123.4 (2)H20A—C20—H20B109.5
N3—C10—N2116.7 (2)C17—C20—H20C109.5
C12—C11—C16120.9 (3)H20A—C20—H20C109.5
C12—C11—N2119.9 (3)H20B—C20—H20C109.5
C16—C11—N2119.2 (3)C10—N1—C7116.0 (2)
C11—C12—C13119.1 (3)C10—N2—C9122.7 (2)
C11—C12—H12120.4C10—N2—C11120.2 (2)
C13—C12—H12120.4C9—N2—C11117.1 (2)
C14—C13—C12120.5 (3)C10—N3—C17126.0 (2)
C14—C13—H13119.8C10—N3—H3A117.0
C12—C13—H13119.8C17—N3—H3A117.0
C13—C14—C15120.4 (3)C8—S1—C190.32 (13)
C6—C1—C2—C30.3 (5)C14—C15—C16—C111.7 (5)
S1—C1—C2—C3179.9 (2)C12—C11—C16—C152.7 (5)
C1—C2—C3—C40.2 (5)N2—C11—C16—C15177.4 (3)
C2—C3—C4—C50.9 (5)N3—C10—N1—C7179.5 (2)
C3—C4—C5—C61.1 (5)N2—C10—N1—C70.5 (4)
C4—C5—C6—C10.7 (4)C8—C7—N1—C101.6 (4)
C4—C5—C6—C7179.2 (3)C6—C7—N1—C10176.3 (3)
C2—C1—C6—C50.0 (4)N1—C10—N2—C90.4 (4)
S1—C1—C6—C5179.9 (2)N3—C10—N2—C9179.6 (2)
C2—C1—C6—C7179.9 (3)N1—C10—N2—C11178.2 (3)
S1—C1—C6—C70.3 (3)N3—C10—N2—C111.8 (4)
C5—C6—C7—N12.1 (5)O1—C9—N2—C10179.6 (3)
C1—C6—C7—N1178.0 (3)C8—C9—N2—C100.3 (4)
C5—C6—C7—C8179.8 (3)O1—C9—N2—C111.0 (4)
C1—C6—C7—C80.1 (3)C8—C9—N2—C11178.4 (2)
N1—C7—C8—C91.7 (4)C12—C11—N2—C10110.5 (3)
C6—C7—C8—C9176.3 (2)C16—C11—N2—C1069.6 (4)
N1—C7—C8—S1177.7 (2)C12—C11—N2—C970.8 (3)
C6—C7—C8—S10.4 (3)C16—C11—N2—C9109.1 (3)
C7—C8—C9—O1178.6 (3)N1—C10—N3—C1715.9 (4)
S1—C8—C9—O13.1 (5)N2—C10—N3—C17164.2 (3)
C7—C8—C9—N20.7 (4)C19—C17—N3—C1075.1 (4)
S1—C8—C9—N2176.21 (19)C18—C17—N3—C1047.7 (4)
C16—C11—C12—C132.0 (4)C20—C17—N3—C10166.3 (3)
N2—C11—C12—C13178.2 (3)C7—C8—S1—C10.4 (2)
C11—C12—C13—C140.2 (5)C9—C8—S1—C1176.2 (3)
C12—C13—C14—C150.8 (5)C2—C1—S1—C8179.8 (3)
C13—C14—C15—C160.0 (5)C6—C1—S1—C80.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19C···N10.962.573.163 (4)120
C18—H18A···N10.962.432.986 (4)117
C18—H18A···Cgi0.962.713.454 (4)135
Symmetry code: (i) x+1, y+1, z+2.
 

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