Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043005/hb2161sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043005/hb2161IIIasup2.hkl |
CCDC reference: 612552
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.087
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C4 ... 1.43 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6' .. N4 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. BR .. 2.96 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: 2 authors are involved in the synthesis, 1 in the spectroscopic characterization, 1 in the X ray data collections and 2 in the structure resolution. |
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C12H7BrN6 | F(000) = 624 |
Mr = 315.15 | Dx = 1.756 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8516 reflections |
a = 7.7153 (3) Å | θ = 2.9–26.0° |
b = 7.6270 (4) Å | µ = 3.44 mm−1 |
c = 20.3497 (7) Å | T = 200 K |
β = 95.560 (2)° | Prism, orange |
V = 1191.84 (9) Å3 | 0.18 × 0.16 × 0.1 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 2000 reflections with I > 2σ(I) |
Horizonally mounted graphite crystal monochromator | Rint = 0.062 |
φ scans and ω scans winth κ offsets | θmax = 26.1°, θmin = 2.9° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −9→9 |
Tmin = 0.548, Tmax = 0.709 | k = −8→9 |
7624 measured reflections | l = −25→25 |
2361 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0505P)2 + 0.2909P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.087 | (Δ/σ)max = 0.026 |
S = 1.05 | Δρmax = 0.76 e Å−3 |
2361 reflections | Δρmin = −0.98 e Å−3 |
173 parameters |
Experimental. (II) δ (CDCl3) 1.44 (3H, t J 7.0?Hz, OCH2CH3), 4.47 (2H, q J 7.0?Hz, OCH2CH3), 7.45 (1H, t J 8.0 Hz, H-5') 7.65–7.71 (2H, m, H-4' and H-6'), 7.88–7.93 (1H, m, H-2'), 8.22 (1H, s, H—C=N). (IIIa) λmax (EtOH, ε) 218 (14815) 311 (8653) nm; νmax (Nujol) 3459, 3294, 3066, 2235, 1646, 1587, 1571, 1557, 1481, 1463, 1383, 1278, 1202, 1135, 1072, 1006, 892, 797, 698?cm-1; δ (acetone-d6) 6.75 (2H, very br s, NH2), 7.69 (1H, t J 7.8 Hz, H-5'), 7.70–7.89 (2H, m, H-4'and H-6'), 8.03 (1H, t J 1.8 Hz, H-2'), 8.47 (1H, s, H-5). 13 C (acetone-d6+DMSO-d6) 157.2 (C7), 155.1 (C5), 151.6 (C3), 146.2 (C3a), 140.2 (C1'), 133.4, 132.0, 129.1, 125.1, 122.8 (C3'), 120.4 (C7a), 112.4 (CN). Found: (M++1) 315.0007. Expected for C12H8N6 79Br: 314.9994. |
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. |
x | y | z | Uiso*/Ueq | ||
N6 | 0.1980 (3) | 0.4330 (3) | −0.03637 (11) | 0.0297 (5) | |
C1' | 0.4865 (3) | 0.1784 (4) | 0.14990 (12) | 0.0263 (5) | |
N1 | 0.5115 (3) | 0.1960 (3) | 0.08155 (11) | 0.0273 (5) | |
C9 | 0.5060 (4) | 0.2681 (3) | −0.02436 (13) | 0.0258 (5) | |
C7 | 0.2458 (3) | 0.3602 (3) | 0.02250 (13) | 0.0277 (5) | |
N4 | 0.4545 (3) | 0.3379 (3) | −0.08434 (11) | 0.0295 (5) | |
C2' | 0.5206 (3) | 0.0169 (3) | 0.17933 (13) | 0.0284 (6) | |
H2' | 0.5539 | −0.0802 | 0.1541 | 0.034* | |
C3 | 0.6578 (3) | 0.1714 (3) | −0.00269 (13) | 0.0276 (5) | |
N2 | 0.6607 (3) | 0.1295 (3) | 0.06115 (11) | 0.0292 (5) | |
C4 | 0.7940 (4) | 0.1219 (4) | −0.04168 (14) | 0.0338 (6) | |
N7 | 0.1352 (3) | 0.3695 (3) | 0.06892 (11) | 0.0347 (5) | |
H7A | 0.0342 | 0.4224 | 0.0604 | 0.042* | |
H7B | 0.1634 | 0.3227 | 0.108 | 0.042* | |
C8 | 0.4134 (4) | 0.2793 (3) | 0.03087 (13) | 0.0257 (5) | |
C5 | 0.3032 (4) | 0.4181 (3) | −0.08522 (13) | 0.0302 (6) | |
H5 | 0.2627 | 0.4729 | −0.1258 | 0.036* | |
Br | 0.55734 (4) | −0.22152 (4) | 0.285832 (13) | 0.03521 (14) | |
C5' | 0.4216 (4) | 0.2997 (3) | 0.25268 (14) | 0.0308 (6) | |
H5' | 0.3876 | 0.3964 | 0.2779 | 0.037* | |
C6' | 0.4381 (3) | 0.3218 (4) | 0.18626 (14) | 0.0282 (5) | |
H6' | 0.4168 | 0.4327 | 0.1658 | 0.034* | |
C3' | 0.5055 (3) | −0.0002 (4) | 0.24571 (13) | 0.0277 (5) | |
C4' | 0.4538 (4) | 0.1390 (4) | 0.28326 (13) | 0.0305 (6) | |
H4' | 0.4408 | 0.1244 | 0.3289 | 0.037* | |
N3 | 0.8941 (4) | 0.0828 (4) | −0.07707 (14) | 0.0516 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N6 | 0.0313 (12) | 0.0285 (11) | 0.0291 (12) | 0.0014 (9) | 0.0018 (9) | 0.0006 (9) |
C1' | 0.0278 (12) | 0.0310 (13) | 0.0199 (12) | 0.0009 (11) | 0.0014 (10) | 0.0007 (10) |
N1 | 0.0302 (11) | 0.0260 (11) | 0.0264 (11) | 0.0055 (9) | 0.0060 (9) | −0.0001 (9) |
C9 | 0.0316 (14) | 0.0218 (12) | 0.0242 (13) | −0.0025 (10) | 0.0044 (11) | −0.0025 (9) |
C7 | 0.0320 (13) | 0.0224 (13) | 0.0289 (13) | 0.0005 (10) | 0.0034 (11) | −0.0014 (10) |
N4 | 0.0373 (12) | 0.0267 (11) | 0.0245 (11) | −0.0020 (10) | 0.0027 (9) | −0.0005 (9) |
C2' | 0.0333 (14) | 0.0250 (13) | 0.0268 (13) | 0.0032 (11) | 0.0020 (11) | −0.0020 (10) |
C3 | 0.0337 (14) | 0.0233 (12) | 0.0264 (13) | 0.0011 (11) | 0.0063 (11) | −0.0031 (10) |
N2 | 0.0314 (12) | 0.0276 (12) | 0.0294 (11) | 0.0021 (9) | 0.0071 (9) | −0.0001 (9) |
C4 | 0.0372 (15) | 0.0338 (15) | 0.0309 (14) | 0.0030 (12) | 0.0055 (12) | 0.0023 (11) |
N7 | 0.0336 (12) | 0.0428 (14) | 0.0284 (12) | 0.0109 (11) | 0.0059 (10) | 0.0063 (10) |
C8 | 0.0328 (14) | 0.0203 (12) | 0.0238 (13) | −0.0011 (10) | 0.0016 (11) | 0.0003 (9) |
C5 | 0.0367 (14) | 0.0279 (14) | 0.0254 (13) | −0.0008 (11) | 0.0002 (11) | 0.0034 (10) |
Br | 0.0453 (2) | 0.0283 (2) | 0.03189 (19) | 0.00302 (12) | 0.00313 (13) | 0.00509 (10) |
C5' | 0.0354 (14) | 0.0281 (14) | 0.0291 (14) | 0.0037 (11) | 0.0045 (11) | −0.0050 (11) |
C6' | 0.0308 (13) | 0.0237 (12) | 0.0302 (14) | 0.0035 (10) | 0.0036 (11) | 0.0020 (11) |
C3' | 0.0287 (13) | 0.0263 (13) | 0.0278 (13) | −0.0024 (10) | 0.0006 (10) | −0.0008 (10) |
C4' | 0.0344 (14) | 0.0331 (15) | 0.0242 (13) | 0.0001 (11) | 0.0042 (11) | 0.0018 (10) |
N3 | 0.0478 (16) | 0.0629 (19) | 0.0471 (16) | 0.0126 (14) | 0.0197 (13) | 0.0038 (14) |
N6—C7 | 1.339 (3) | C2'—H2' | 0.95 |
N6—C5 | 1.348 (3) | C3—N2 | 1.336 (3) |
C1'—C2' | 1.384 (4) | C3—C4 | 1.427 (4) |
C1'—C6' | 1.392 (4) | C4—N3 | 1.145 (4) |
C1'—N1 | 1.429 (3) | N7—H7A | 0.88 |
N1—N2 | 1.359 (3) | N7—H7B | 0.88 |
N1—C8 | 1.374 (3) | C5—H5 | 0.95 |
C9—N4 | 1.355 (3) | Br—C3' | 1.901 (3) |
C9—C8 | 1.392 (4) | C5'—C6' | 1.380 (4) |
C9—C3 | 1.418 (4) | C5'—C4' | 1.386 (4) |
C7—N7 | 1.335 (3) | C5'—H5' | 0.95 |
C7—C8 | 1.428 (4) | C6'—H6' | 0.95 |
N4—C5 | 1.317 (4) | C3'—C4' | 1.389 (4) |
C2'—C3' | 1.373 (4) | C4'—H4' | 0.95 |
C7—N6—C5 | 119.4 (2) | C7—N7—H7A | 120 |
C2'—C1'—C6' | 121.3 (2) | C7—N7—H7B | 120 |
C2'—C1'—N1 | 117.8 (2) | H7A—N7—H7B | 120 |
C6'—C1'—N1 | 120.8 (2) | N1—C8—C9 | 106.8 (2) |
N2—N1—C8 | 111.4 (2) | N1—C8—C7 | 135.7 (2) |
N2—N1—C1' | 117.4 (2) | C9—C8—C7 | 117.4 (2) |
C8—N1—C1' | 131.1 (2) | N4—C5—N6 | 128.7 (2) |
N4—C9—C8 | 125.1 (2) | N4—C5—H5 | 115.6 |
N4—C9—C3 | 130.2 (2) | N6—C5—H5 | 115.6 |
C8—C9—C3 | 104.7 (2) | C6'—C5'—C4' | 121.2 (2) |
N7—C7—N6 | 118.1 (2) | C6'—C5'—H5' | 119.4 |
N7—C7—C8 | 124.9 (2) | C4'—C5'—H5' | 119.4 |
N6—C7—C8 | 117.0 (2) | C5'—C6'—C1' | 118.7 (2) |
C5—N4—C9 | 112.1 (2) | C5'—C6'—H6' | 120.7 |
C3'—C2'—C1' | 118.6 (2) | C1'—C6'—H6' | 120.7 |
C3'—C2'—H2' | 120.7 | C2'—C3'—C4' | 121.7 (2) |
C1'—C2'—H2' | 120.7 | C2'—C3'—Br | 118.2 (2) |
N2—C3—C9 | 111.2 (2) | C4'—C3'—Br | 120.1 (2) |
N2—C3—C4 | 122.3 (2) | C5'—C4'—C3' | 118.5 (2) |
C9—C3—C4 | 126.5 (2) | C5'—C4'—H4' | 120.7 |
C3—N2—N1 | 105.8 (2) | C3'—C4'—H4' | 120.7 |
N3—C4—C3 | 174.8 (3) | ||
C2'—C1'—N1—N2 | −45.9 (3) | N2—N1—C8—C7 | 175.1 (3) |
C6'—C1'—N1—N2 | 130.9 (3) | C1'—N1—C8—C7 | −8.8 (5) |
C2'—C1'—N1—C8 | 138.2 (3) | N4—C9—C8—N1 | −178.5 (2) |
C6'—C1'—N1—C8 | −45.0 (4) | C3—C9—C8—N1 | 1.4 (3) |
C5—N6—C7—N7 | −176.7 (2) | N4—C9—C8—C7 | 4.5 (4) |
C5—N6—C7—C8 | 3.8 (4) | C3—C9—C8—C7 | −175.6 (2) |
C8—C9—N4—C5 | −0.6 (4) | N7—C7—C8—N1 | −1.2 (5) |
C3—C9—N4—C5 | 179.5 (3) | N6—C7—C8—N1 | 178.2 (3) |
C6'—C1'—C2'—C3' | 0.2 (4) | N7—C7—C8—C9 | 174.7 (3) |
N1—C1'—C2'—C3' | 176.9 (2) | N6—C7—C8—C9 | −5.9 (3) |
N4—C9—C3—N2 | 178.7 (3) | C9—N4—C5—N6 | −2.0 (4) |
C8—C9—C3—N2 | −1.2 (3) | C7—N6—C5—N4 | 0.3 (4) |
N4—C9—C3—C4 | −1.3 (5) | C4'—C5'—C6'—C1' | 0.6 (4) |
C8—C9—C3—C4 | 178.8 (3) | C2'—C1'—C6'—C5' | −1.1 (4) |
C9—C3—N2—N1 | 0.6 (3) | N1—C1'—C6'—C5' | −177.7 (2) |
C4—C3—N2—N1 | −179.5 (2) | C1'—C2'—C3'—C4' | 1.3 (4) |
C8—N1—N2—C3 | 0.3 (3) | C1'—C2'—C3'—Br | −178.8 (2) |
C1'—N1—N2—C3 | −176.4 (2) | C6'—C5'—C4'—C3' | 0.8 (4) |
N2—N1—C8—C9 | −1.1 (3) | C2'—C3'—C4'—C5' | −1.7 (4) |
C1'—N1—C8—C9 | 175.0 (2) | Br—C3'—C4'—C5' | 178.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7A···N6i | 0.88 | 2.12 | 2.998 (3) | 175 |
C2′—H2′···N4ii | 0.95 | 2.42 | 3.342 (3) | 163 |
C6′—H6′···N4iii | 0.95 | 2.67 | 3.472 (3) | 143 |
N7—H7B···Briv | 0.88 | 2.9 | 3.504 (2) | 128 |
C5—H5···Brv | 0.95 | 2.96 | 3.857 (3) | 157 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y, −z; (iii) −x+1, −y+1, −z; (iv) −x+1/2, y+1/2, −z+1/2; (v) x−1/2, −y+1/2, z−1/2. |
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