In the title compound, C
20H
19N
3OS, 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
CCDC reference: 630024
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (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
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-3
H-benzo[4,5]thieno[3,2-
e]pyrimidin-4-one
top
Crystal data top
C20H19N3OS | Z = 2 |
Mr = 349.44 | F(000) = 368 |
Triclinic, P1 | Dx = 1.306 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7106 (15) Å | Cell parameters from 1055 reflections |
b = 10.1139 (15) Å | θ = 2.3–25.0° |
c = 10.5568 (16) Å | µ = 0.20 mm−1 |
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 tube | 2179 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −11→9 |
Tmin = 0.962, Tmax = 0.981 | k = −11→11 |
4495 measured reflections | l = −12→12 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-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 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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 | Uiso*/Ueq | |
C1 | 0.7806 (3) | 0.1215 (3) | 1.1700 (3) | 0.0436 (7) | |
C2 | 0.8745 (4) | 0.0945 (3) | 1.3019 (3) | 0.0519 (8) | |
H2 | 0.9696 | 0.0659 | 1.3191 | 0.062* | |
C3 | 0.8220 (4) | 0.1114 (3) | 1.4056 (3) | 0.0571 (9) | |
H3 | 0.8837 | 0.0939 | 1.4942 | 0.068* | |
C4 | 0.6811 (4) | 0.1533 (3) | 1.3835 (3) | 0.0561 (8) | |
H4 | 0.6490 | 0.1624 | 1.4559 | 0.067* | |
C5 | 0.5883 (4) | 0.1817 (3) | 1.2541 (3) | 0.0506 (8) | |
H5 | 0.4941 | 0.2115 | 1.2392 | 0.061* | |
C6 | 0.6376 (3) | 0.1651 (3) | 1.1454 (3) | 0.0390 (7) | |
C7 | 0.5593 (3) | 0.1870 (3) | 1.0031 (3) | 0.0374 (6) | |
C8 | 0.6435 (3) | 0.1597 (3) | 0.9263 (3) | 0.0394 (7) | |
C9 | 0.5906 (3) | 0.1828 (3) | 0.7852 (3) | 0.0421 (7) | |
C10 | 0.3683 (3) | 0.2556 (3) | 0.8253 (3) | 0.0392 (7) | |
C11 | 0.3844 (3) | 0.2634 (3) | 0.6002 (3) | 0.0429 (7) | |
C12 | 0.3274 (3) | 0.1578 (3) | 0.4709 (3) | 0.0482 (7) | |
H12 | 0.3313 | 0.0663 | 0.4720 | 0.058* | |
C13 | 0.2638 (4) | 0.1887 (4) | 0.3384 (3) | 0.0629 (10) | |
H13 | 0.2243 | 0.1175 | 0.2498 | 0.075* | |
C14 | 0.2586 (4) | 0.3230 (5) | 0.3369 (4) | 0.0685 (11) | |
H14 | 0.2145 | 0.3426 | 0.2472 | 0.082* | |
C15 | 0.3184 (4) | 0.4301 (4) | 0.4677 (4) | 0.0668 (10) | |
H15 | 0.3148 | 0.5216 | 0.4665 | 0.080* | |
C16 | 0.3835 (4) | 0.3999 (3) | 0.6001 (3) | 0.0544 (8) | |
H16 | 0.4266 | 0.4711 | 0.6889 | 0.065* | |
C17 | 0.1484 (3) | 0.3658 (3) | 0.8517 (3) | 0.0474 (8) | |
C18 | 0.2579 (4) | 0.4756 (3) | 0.9946 (4) | 0.0670 (10) | |
H18A | 0.3297 | 0.4321 | 1.0613 | 0.101* | |
H18B | 0.1991 | 0.5247 | 1.0389 | 0.101* | |
H18C | 0.3142 | 0.5395 | 0.9739 | 0.101* | |
C19 | 0.0709 (4) | 0.2560 (4) | 0.8828 (4) | 0.0650 (9) | |
H19A | −0.0083 | 0.1948 | 0.7915 | 0.098* | |
H19B | 0.0250 | 0.2992 | 0.9439 | 0.098* | |
H19C | 0.1467 | 0.2040 | 0.9331 | 0.098* | |
C20 | 0.0263 (4) | 0.4328 (4) | 0.7505 (4) | 0.0788 (12) | |
H20A | 0.0763 | 0.5094 | 0.7398 | 0.118* | |
H20B | −0.0410 | 0.4655 | 0.7925 | 0.118* | |
H20C | −0.0337 | 0.3658 | 0.6554 | 0.118* | |
N1 | 0.4199 (3) | 0.2336 (2) | 0.9536 (2) | 0.0435 (6) | |
N2 | 0.4472 (3) | 0.2328 (2) | 0.7398 (2) | 0.0387 (6) | |
N3 | 0.2324 (3) | 0.3025 (3) | 0.7688 (2) | 0.0483 (6) | |
H3A | 0.1904 | 0.2952 | 0.6762 | 0.058* | |
O1 | 0.6564 (2) | 0.1649 (2) | 0.7083 (2) | 0.0569 (6) | |
S1 | 0.81909 (9) | 0.10819 (9) | 1.02092 (8) | 0.0511 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0444 (17) | 0.0512 (18) | 0.0392 (16) | 0.0118 (14) | 0.0208 (13) | 0.0164 (14) |
C2 | 0.0534 (19) | 0.056 (2) | 0.0472 (18) | 0.0157 (16) | 0.0187 (15) | 0.0232 (16) |
C3 | 0.071 (2) | 0.059 (2) | 0.0421 (18) | 0.0151 (17) | 0.0221 (17) | 0.0237 (16) |
C4 | 0.073 (2) | 0.063 (2) | 0.0490 (19) | 0.0175 (18) | 0.0368 (17) | 0.0266 (17) |
C5 | 0.0551 (19) | 0.059 (2) | 0.0489 (18) | 0.0152 (16) | 0.0308 (16) | 0.0216 (16) |
C6 | 0.0456 (17) | 0.0389 (16) | 0.0373 (15) | 0.0063 (13) | 0.0213 (13) | 0.0151 (13) |
C7 | 0.0425 (16) | 0.0346 (15) | 0.0379 (15) | 0.0056 (12) | 0.0206 (13) | 0.0114 (12) |
C8 | 0.0439 (17) | 0.0401 (16) | 0.0373 (15) | 0.0100 (13) | 0.0203 (13) | 0.0130 (13) |
C9 | 0.0404 (16) | 0.0487 (18) | 0.0388 (16) | 0.0069 (13) | 0.0203 (14) | 0.0120 (13) |
C10 | 0.0416 (16) | 0.0417 (17) | 0.0391 (15) | 0.0103 (13) | 0.0212 (13) | 0.0146 (13) |
C11 | 0.0382 (16) | 0.060 (2) | 0.0379 (16) | 0.0113 (14) | 0.0204 (13) | 0.0210 (15) |
C12 | 0.0499 (18) | 0.057 (2) | 0.0438 (17) | 0.0136 (15) | 0.0262 (15) | 0.0162 (15) |
C13 | 0.053 (2) | 0.100 (3) | 0.0355 (17) | 0.0200 (19) | 0.0223 (16) | 0.0159 (18) |
C14 | 0.063 (2) | 0.112 (3) | 0.055 (2) | 0.037 (2) | 0.0336 (19) | 0.049 (2) |
C15 | 0.071 (2) | 0.079 (3) | 0.066 (2) | 0.025 (2) | 0.033 (2) | 0.042 (2) |
C16 | 0.062 (2) | 0.055 (2) | 0.0499 (19) | 0.0110 (16) | 0.0250 (16) | 0.0224 (16) |
C17 | 0.0453 (17) | 0.0555 (19) | 0.0427 (17) | 0.0169 (15) | 0.0227 (14) | 0.0115 (15) |
C18 | 0.070 (2) | 0.058 (2) | 0.072 (2) | 0.0150 (18) | 0.037 (2) | 0.0092 (18) |
C19 | 0.056 (2) | 0.069 (2) | 0.076 (2) | 0.0080 (18) | 0.0385 (19) | 0.0176 (19) |
C20 | 0.079 (3) | 0.096 (3) | 0.074 (3) | 0.052 (2) | 0.037 (2) | 0.038 (2) |
N1 | 0.0402 (14) | 0.0588 (16) | 0.0401 (13) | 0.0152 (12) | 0.0225 (11) | 0.0206 (12) |
N2 | 0.0420 (14) | 0.0442 (14) | 0.0352 (12) | 0.0121 (11) | 0.0194 (11) | 0.0166 (11) |
N3 | 0.0442 (14) | 0.0721 (18) | 0.0361 (13) | 0.0243 (13) | 0.0212 (11) | 0.0217 (13) |
O1 | 0.0530 (13) | 0.0881 (17) | 0.0470 (12) | 0.0269 (12) | 0.0336 (11) | 0.0269 (12) |
S1 | 0.0469 (5) | 0.0716 (6) | 0.0465 (5) | 0.0234 (4) | 0.0264 (4) | 0.0259 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.393 (4) | C12—C13 | 1.384 (4) |
C1—C6 | 1.402 (4) | C12—H12 | 0.9300 |
C1—S1 | 1.745 (3) | C13—C14 | 1.364 (5) |
C2—C3 | 1.372 (4) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C15 | 1.382 (5) |
C3—C4 | 1.382 (4) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C16 | 1.380 (4) |
C4—C5 | 1.377 (4) | C15—H15 | 0.9300 |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C6 | 1.400 (4) | C17—N3 | 1.485 (3) |
C5—H5 | 0.9300 | C17—C19 | 1.506 (4) |
C6—C7 | 1.437 (3) | C17—C18 | 1.519 (4) |
C7—N1 | 1.367 (3) | C17—C20 | 1.521 (4) |
C7—C8 | 1.371 (4) | C18—H18A | 0.9600 |
C8—C9 | 1.433 (4) | C18—H18B | 0.9600 |
C8—S1 | 1.732 (3) | C18—H18C | 0.9600 |
C9—O1 | 1.219 (3) | C19—H19A | 0.9600 |
C9—N2 | 1.415 (3) | C19—H19B | 0.9600 |
C10—N1 | 1.304 (3) | C19—H19C | 0.9600 |
C10—N3 | 1.346 (3) | C20—H20A | 0.9600 |
C10—N2 | 1.400 (3) | C20—H20B | 0.9600 |
C11—C12 | 1.366 (4) | C20—H20C | 0.9600 |
C11—C16 | 1.381 (4) | N3—H3A | 0.8600 |
C11—N2 | 1.448 (3) | | |
| | | |
C2—C1—C6 | 120.6 (3) | C13—C14—H14 | 119.8 |
C2—C1—S1 | 127.2 (2) | C15—C14—H14 | 119.8 |
C6—C1—S1 | 112.20 (19) | C16—C15—C14 | 119.3 (3) |
C3—C2—C1 | 117.9 (3) | C16—C15—H15 | 120.3 |
C3—C2—H2 | 121.1 | C14—C15—H15 | 120.3 |
C1—C2—H2 | 121.1 | C15—C16—C11 | 119.7 (3) |
C2—C3—C4 | 122.6 (3) | C15—C16—H16 | 120.2 |
C2—C3—H3 | 118.7 | C11—C16—H16 | 120.2 |
C4—C3—H3 | 118.7 | N3—C17—C19 | 110.5 (3) |
C5—C4—C3 | 119.9 (3) | N3—C17—C18 | 110.8 (3) |
C5—C4—H4 | 120.0 | C19—C17—C18 | 110.5 (3) |
C3—C4—H4 | 120.0 | N3—C17—C20 | 105.4 (2) |
C4—C5—C6 | 119.1 (3) | C19—C17—C20 | 109.8 (3) |
C4—C5—H5 | 120.4 | C18—C17—C20 | 109.7 (3) |
C6—C5—H5 | 120.4 | C17—C18—H18A | 109.5 |
C5—C6—C1 | 119.8 (2) | C17—C18—H18B | 109.5 |
C5—C6—C7 | 128.4 (3) | H18A—C18—H18B | 109.5 |
C1—C6—C7 | 111.7 (2) | C17—C18—H18C | 109.5 |
N1—C7—C8 | 124.7 (2) | H18A—C18—H18C | 109.5 |
N1—C7—C6 | 123.5 (2) | H18B—C18—H18C | 109.5 |
C8—C7—C6 | 111.8 (2) | C17—C19—H19A | 109.5 |
C7—C8—C9 | 120.8 (3) | C17—C19—H19B | 109.5 |
C7—C8—S1 | 113.9 (2) | H19A—C19—H19B | 109.5 |
C9—C8—S1 | 125.1 (2) | C17—C19—H19C | 109.5 |
O1—C9—N2 | 120.9 (2) | H19A—C19—H19C | 109.5 |
O1—C9—C8 | 126.8 (3) | H19B—C19—H19C | 109.5 |
N2—C9—C8 | 112.3 (2) | C17—C20—H20A | 109.5 |
N1—C10—N3 | 119.9 (2) | C17—C20—H20B | 109.5 |
N1—C10—N2 | 123.4 (2) | H20A—C20—H20B | 109.5 |
N3—C10—N2 | 116.7 (2) | C17—C20—H20C | 109.5 |
C12—C11—C16 | 120.9 (3) | H20A—C20—H20C | 109.5 |
C12—C11—N2 | 119.9 (3) | H20B—C20—H20C | 109.5 |
C16—C11—N2 | 119.2 (3) | C10—N1—C7 | 116.0 (2) |
C11—C12—C13 | 119.1 (3) | C10—N2—C9 | 122.7 (2) |
C11—C12—H12 | 120.4 | C10—N2—C11 | 120.2 (2) |
C13—C12—H12 | 120.4 | C9—N2—C11 | 117.1 (2) |
C14—C13—C12 | 120.5 (3) | C10—N3—C17 | 126.0 (2) |
C14—C13—H13 | 119.8 | C10—N3—H3A | 117.0 |
C12—C13—H13 | 119.8 | C17—N3—H3A | 117.0 |
C13—C14—C15 | 120.4 (3) | C8—S1—C1 | 90.32 (13) |
| | | |
C6—C1—C2—C3 | 0.3 (5) | C14—C15—C16—C11 | −1.7 (5) |
S1—C1—C2—C3 | −179.9 (2) | C12—C11—C16—C15 | 2.7 (5) |
C1—C2—C3—C4 | 0.2 (5) | N2—C11—C16—C15 | −177.4 (3) |
C2—C3—C4—C5 | −0.9 (5) | N3—C10—N1—C7 | −179.5 (2) |
C3—C4—C5—C6 | 1.1 (5) | N2—C10—N1—C7 | 0.5 (4) |
C4—C5—C6—C1 | −0.7 (4) | C8—C7—N1—C10 | −1.6 (4) |
C4—C5—C6—C7 | 179.2 (3) | C6—C7—N1—C10 | 176.3 (3) |
C2—C1—C6—C5 | 0.0 (4) | N1—C10—N2—C9 | 0.4 (4) |
S1—C1—C6—C5 | −179.9 (2) | N3—C10—N2—C9 | −179.6 (2) |
C2—C1—C6—C7 | −179.9 (3) | N1—C10—N2—C11 | −178.2 (3) |
S1—C1—C6—C7 | 0.3 (3) | N3—C10—N2—C11 | 1.8 (4) |
C5—C6—C7—N1 | 2.1 (5) | O1—C9—N2—C10 | −179.6 (3) |
C1—C6—C7—N1 | −178.0 (3) | C8—C9—N2—C10 | −0.3 (4) |
C5—C6—C7—C8 | −179.8 (3) | O1—C9—N2—C11 | −1.0 (4) |
C1—C6—C7—C8 | 0.1 (3) | C8—C9—N2—C11 | 178.4 (2) |
N1—C7—C8—C9 | 1.7 (4) | C12—C11—N2—C10 | −110.5 (3) |
C6—C7—C8—C9 | −176.3 (2) | C16—C11—N2—C10 | 69.6 (4) |
N1—C7—C8—S1 | 177.7 (2) | C12—C11—N2—C9 | 70.8 (3) |
C6—C7—C8—S1 | −0.4 (3) | C16—C11—N2—C9 | −109.1 (3) |
C7—C8—C9—O1 | 178.6 (3) | N1—C10—N3—C17 | 15.9 (4) |
S1—C8—C9—O1 | 3.1 (5) | N2—C10—N3—C17 | −164.2 (3) |
C7—C8—C9—N2 | −0.7 (4) | C19—C17—N3—C10 | −75.1 (4) |
S1—C8—C9—N2 | −176.21 (19) | C18—C17—N3—C10 | 47.7 (4) |
C16—C11—C12—C13 | −2.0 (4) | C20—C17—N3—C10 | 166.3 (3) |
N2—C11—C12—C13 | 178.2 (3) | C7—C8—S1—C1 | 0.4 (2) |
C11—C12—C13—C14 | 0.2 (5) | C9—C8—S1—C1 | 176.2 (3) |
C12—C13—C14—C15 | 0.8 (5) | C2—C1—S1—C8 | 179.8 (3) |
C13—C14—C15—C16 | 0.0 (5) | C6—C1—S1—C8 | −0.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19C···N1 | 0.96 | 2.57 | 3.163 (4) | 120 |
C18—H18A···N1 | 0.96 | 2.43 | 2.986 (4) | 117 |
C18—H18A···Cgi | 0.96 | 2.71 | 3.454 (4) | 135 |
Symmetry code: (i) −x+1, −y+1, −z+2. |