Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029947/sg2180sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029947/sg2180Isup2.hkl |
CCDC reference: 655015
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.109
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.36 From the CIF: _reflns_number_total 1623 Count of symmetry unique reflns 948 Completeness (_total/calc) 171.20% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 675 Fraction of Friedel pairs measured 0.712 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Allen et al. (1987); Barton et al. (1985); Hökelek et al. (1990, 1991a, 1991b); Hansen et al. (2007); Holt & Fiksdahl (2006); Stockmann & Fiksdahl (2007); Van der Meer (1972).
Thieno[3,2-c]-7-azacinnoline (I) was prepared by intramolecular diazo coupling of the diazonium ion intermediate, made by NOBF4 diazotization (Holt & Fiksdahl, 2006) of the 3-amino-4-(thiophen-2-yl)pyridine precursor. Single crystals were grown by crystallization from ethyl acetate (Stockmann & Fiksdahl, 2007).
The H atoms were placed in idealized locations C—H = 0.93 Å and refined as riding with Uiso(H) = 1.2Ueq(C).
The crystal structure of the title compound (I) was solved as part of a study of new tris-heterocyclic compounds with potential biological activity (Stockmann & Fiksdahl, 2007). Thieno[c]cinnolines (Barton et al., 1985) have been described in the literature and the crystal structure of benzo[c]cinnoline (9,10-diazaphenanthrene) has been solved (Van der Meer,1972). A view of molecule (I) with the atomic numbering is presented in Fig 1. The bond lengths are within the normal range of such bonds (Allen et al., 1987) and also in accordance with the regio-isomer thieno[2,3-c]-7-azacinnoline (Hansen et al., 2007) and other benzo[c]cinnoline derivatives (Hökelek et al., 1990, 1991a,1991b).
For related literature, see: Allen et al. (1987); Barton et al. (1985); Hökelek et al. (1990, 1991a, 1991b); Hansen et al. (2007); Holt & Fiksdahl (2006); Stockmann & Fiksdahl (2007); Van der Meer (1972).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.
Fig. 1. A view of I with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
C9H5N3S | F(000) = 384.00 |
Mr = 187.22 | Dx = 1.545 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2c -2n | Cell parameters from 2489 reflections |
a = 13.0233 (13) Å | θ = 2.6–26.3° |
b = 15.969 (3) Å | µ = 0.35 mm−1 |
c = 3.869 (1) Å | T = 293 K |
V = 804.6 (3) Å3 | Needle, colorless |
Z = 4 | 0.43 × 0.06 × 0.05 mm |
Rigaku Saturn diffractometer | 1368 reflections with F2 > 2σ(F2) |
Detector resolution: 7.31 pixels mm-1 | Rint = 0.043 |
ω scans | θmax = 26.4° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −16→16 |
Tmin = 0.970, Tmax = 0.990 | k = −19→19 |
5659 measured reflections | l = −4→4 |
1623 independent reflections |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0638P)2 + 0.0832P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.043 | (Δ/σ)max = 0.001 |
wR(F2) = 0.110 | Δρmax = 0.24 e Å−3 |
S = 0.99 | Δρmin = −0.20 e Å−3 |
1623 reflections | Absolute structure: Flack (1983), 678 Friedel pairs |
118 parameters | Absolute structure parameter: 0.15 (13) |
H-atom parameters constrained |
C9H5N3S | V = 804.6 (3) Å3 |
Mr = 187.22 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 13.0233 (13) Å | µ = 0.35 mm−1 |
b = 15.969 (3) Å | T = 293 K |
c = 3.869 (1) Å | 0.43 × 0.06 × 0.05 mm |
Rigaku Saturn diffractometer | 1623 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 1368 reflections with F2 > 2σ(F2) |
Tmin = 0.970, Tmax = 0.990 | Rint = 0.043 |
5659 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.110 | Δρmax = 0.24 e Å−3 |
S = 0.99 | Δρmin = −0.20 e Å−3 |
1623 reflections | Absolute structure: Flack (1983), 678 Friedel pairs |
118 parameters | Absolute structure parameter: 0.15 (13) |
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.48118 (5) | 0.39555 (5) | −0.2592 (2) | 0.0501 (2) | |
N3 | 0.11539 (19) | 0.53593 (13) | 0.2017 (8) | 0.0518 (6) | |
N2 | 0.18936 (17) | 0.31858 (12) | 0.2581 (8) | 0.0480 (5) | |
N1 | 0.26250 (19) | 0.26614 (14) | 0.1794 (8) | 0.0522 (7) | |
C4 | 0.1992 (2) | 0.40207 (16) | 0.1722 (7) | 0.0385 (6) | |
C8 | 0.28477 (19) | 0.43726 (16) | 0.0052 (6) | 0.0358 (6) | |
C3 | 0.3492 (2) | 0.29597 (17) | 0.0150 (7) | 0.0433 (6) | |
C5 | 0.1168 (2) | 0.45587 (17) | 0.2577 (9) | 0.0464 (6) | |
H5 | 0.0594 | 0.4321 | 0.3619 | 0.056* | |
C7 | 0.2824 (2) | 0.52393 (17) | −0.0661 (8) | 0.0426 (6) | |
H7 | 0.3366 | 0.5498 | −0.1805 | 0.051* | |
C9 | 0.3634 (2) | 0.37936 (17) | −0.0712 (7) | 0.0378 (6) | |
C6 | 0.1989 (2) | 0.56885 (18) | 0.0363 (8) | 0.0489 (7) | |
H6 | 0.1986 | 0.6260 | −0.0095 | 0.059* | |
C2 | 0.4355 (2) | 0.2449 (2) | −0.0781 (10) | 0.0562 (8) | |
H2 | 0.4392 | 0.1874 | −0.0409 | 0.067* | |
C1 | 0.5099 (2) | 0.2903 (2) | −0.2255 (12) | 0.0573 (8) | |
H1 | 0.5714 | 0.2674 | −0.3025 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0385 (3) | 0.0645 (4) | 0.0472 (4) | 0.0017 (3) | 0.0040 (4) | 0.0007 (4) |
N3 | 0.0461 (13) | 0.0451 (13) | 0.0643 (17) | 0.0070 (10) | −0.0060 (14) | −0.0018 (15) |
N2 | 0.0452 (12) | 0.0423 (12) | 0.0564 (14) | −0.0076 (9) | 0.0008 (15) | 0.0024 (13) |
N1 | 0.0520 (14) | 0.0407 (11) | 0.064 (2) | −0.0023 (11) | −0.0039 (13) | 0.0056 (13) |
C4 | 0.0340 (13) | 0.0422 (14) | 0.0393 (18) | −0.0011 (10) | −0.0040 (11) | −0.0002 (11) |
C8 | 0.0337 (14) | 0.0381 (14) | 0.0357 (14) | −0.0019 (10) | −0.0063 (11) | −0.0010 (11) |
C3 | 0.0437 (15) | 0.0386 (14) | 0.0475 (17) | 0.0030 (12) | −0.0063 (13) | 0.0001 (13) |
C5 | 0.0337 (14) | 0.0525 (15) | 0.0530 (17) | −0.0002 (11) | 0.0003 (17) | 0.0012 (18) |
C7 | 0.0398 (15) | 0.0418 (15) | 0.0462 (16) | −0.0066 (11) | −0.0057 (13) | 0.0083 (13) |
C9 | 0.0330 (14) | 0.0474 (15) | 0.0331 (15) | −0.0006 (10) | −0.0037 (12) | −0.0020 (12) |
C6 | 0.0514 (17) | 0.0364 (15) | 0.059 (2) | 0.0013 (13) | −0.0106 (15) | 0.0005 (13) |
C2 | 0.062 (2) | 0.0455 (16) | 0.0614 (18) | 0.0187 (15) | −0.0095 (17) | −0.0075 (16) |
C1 | 0.0488 (17) | 0.069 (2) | 0.054 (2) | 0.0200 (14) | 0.0006 (17) | −0.012 (2) |
S1—C9 | 1.718 (2) | C8—C9 | 1.411 (3) |
S1—C1 | 1.726 (3) | C3—C9 | 1.385 (3) |
N3—C5 | 1.297 (3) | C3—C2 | 1.434 (4) |
N3—C6 | 1.366 (4) | C7—C6 | 1.362 (4) |
N2—N1 | 1.304 (3) | C2—C1 | 1.339 (4) |
N2—C4 | 1.380 (3) | C5—H5 | 0.930 |
N1—C3 | 1.381 (3) | C7—H7 | 0.930 |
C4—C8 | 1.406 (3) | C6—H6 | 0.930 |
C4—C5 | 1.414 (3) | C2—H2 | 0.930 |
C8—C7 | 1.412 (3) | C1—H1 | 0.930 |
C9—S1—C1 | 90.87 (14) | S1—C9—C3 | 111.4 (2) |
C5—N3—C6 | 116.5 (2) | C8—C9—C3 | 118.9 (2) |
N1—N2—C4 | 119.8 (2) | N3—C6—C7 | 124.7 (2) |
N2—N1—C3 | 118.9 (2) | C3—C2—C1 | 111.4 (2) |
N2—C4—C8 | 124.8 (2) | S1—C1—C2 | 113.8 (2) |
N2—C4—C5 | 117.4 (2) | N3—C5—H5 | 117.6 |
C8—C4—C5 | 117.8 (2) | C4—C5—H5 | 117.6 |
C4—C8—C7 | 117.7 (2) | C8—C7—H7 | 120.7 |
C4—C8—C9 | 114.2 (2) | H7—C7—C6 | 120.8 |
C7—C8—C9 | 128.1 (2) | N3—C6—H6 | 117.7 |
N1—C3—C9 | 123.4 (2) | C7—C6—H6 | 117.7 |
N1—C3—C2 | 124.0 (2) | C3—C2—H2 | 124.3 |
C9—C3—C2 | 112.5 (2) | H2—C2—C1 | 124.3 |
N3—C5—C4 | 124.8 (2) | S1—C1—H1 | 123.1 |
C8—C7—C6 | 118.5 (2) | C2—C1—H1 | 123.1 |
S1—C9—C8 | 129.7 (2) | ||
C9—S1—C1—C2 | −0.5 (3) | C5—C4—C8—C9 | −179.94 (19) |
C1—S1—C9—C8 | 179.8 (2) | C4—C8—C7—C6 | 1.4 (4) |
C1—S1—C9—C3 | 0.6 (2) | C4—C8—C9—S1 | −177.9 (2) |
C5—N3—C6—C7 | −1.1 (5) | C4—C8—C9—C3 | 1.2 (3) |
C6—N3—C5—C4 | 2.5 (5) | C7—C8—C9—S1 | 2.3 (4) |
N1—N2—C4—C8 | −0.9 (4) | C7—C8—C9—C3 | −178.5 (2) |
N1—N2—C4—C5 | 178.8 (3) | C9—C8—C7—C6 | −178.9 (2) |
C4—N2—N1—C3 | 0.9 (4) | N1—C3—C9—S1 | 177.9 (2) |
N2—N1—C3—C9 | 0.2 (4) | N1—C3—C9—C8 | −1.4 (4) |
N2—N1—C3—C2 | 178.7 (3) | N1—C3—C2—C1 | −178.2 (3) |
N2—C4—C8—C7 | 179.6 (2) | C9—C3—C2—C1 | 0.4 (4) |
N2—C4—C8—C9 | −0.2 (3) | C2—C3—C9—S1 | −0.7 (3) |
N2—C4—C5—N3 | 178.3 (3) | C2—C3—C9—C8 | −180.0 (2) |
C8—C4—C5—N3 | −1.9 (4) | C8—C7—C6—N3 | −0.8 (4) |
C5—C4—C8—C7 | −0.2 (3) | C3—C2—C1—S1 | 0.1 (3) |
Experimental details
Crystal data | |
Chemical formula | C9H5N3S |
Mr | 187.22 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 293 |
a, b, c (Å) | 13.0233 (13), 15.969 (3), 3.869 (1) |
V (Å3) | 804.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.43 × 0.06 × 0.05 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Multi-scan (Jacobson, 1998) |
Tmin, Tmax | 0.970, 0.990 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 5659, 1623, 1368 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.110, 0.99 |
No. of reflections | 1623 |
No. of parameters | 118 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.20 |
Absolute structure | Flack (1983), 678 Friedel pairs |
Absolute structure parameter | 0.15 (13) |
Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, CrystalStructure (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), CrystalStructure.
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The crystal structure of the title compound (I) was solved as part of a study of new tris-heterocyclic compounds with potential biological activity (Stockmann & Fiksdahl, 2007). Thieno[c]cinnolines (Barton et al., 1985) have been described in the literature and the crystal structure of benzo[c]cinnoline (9,10-diazaphenanthrene) has been solved (Van der Meer,1972). A view of molecule (I) with the atomic numbering is presented in Fig 1. The bond lengths are within the normal range of such bonds (Allen et al., 1987) and also in accordance with the regio-isomer thieno[2,3-c]-7-azacinnoline (Hansen et al., 2007) and other benzo[c]cinnoline derivatives (Hökelek et al., 1990, 1991a,1991b).