Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036975/is2196sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036975/is2196Isup2.hkl |
CCDC reference: 662407
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.084
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.298 0.679 Tmin and Tmax expected: 0.237 0.680 RR = 1.260 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.28 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.78 mm PLAT432_ALERT_2_C Short Inter X...Y Contact C14 .. C14 .. 3.17 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 3 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
The title compound was prepared by the reaction of N-arylidenenaphthalen-2-amine (0.62 g, 2 mmol) and phenylacetaldehyde (0.24 g, 2 mmol) in the presence of iodine (0.05 g) in THF at 340 K for 5 h (yield 72%; m.p. 478–480 K). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a DMF solution.
Elemental analysis calculated: C 73.18, H 3.93, N, 3.41%; found: C 73.25, H 3.88, N 3.20%. 1H NMR (DMSO-d6): 7.38 (d, J = 8.4 Hz, 2H, ArH), 7.39 (s, 5H, ArH), 7.52 (d, J = 8.4 Hz, 2H, ArH), 7.74–7.76 (m, 2H, ArH), 7.99 (d, J = 8.8 Hz, 1H, ArH), 8.09–8.11 (m, 1H, ArH), 8.17 (d, J = 8.8 Hz, 1H, ArH), 9.19 (d, J = 7.6 Hz, 1H, ArH), 9.21 (s, 1H, ArH); IR (cm-1): 3056(ArH), 1678(C=N), 1603, 1584, 1566, 1487, 1472, 1431(phenyl ring).
The H atoms were calculated geometrically (C—H = 0.95 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).
Quinoline and its derivatives represent an important class of nitrogen-containing heterocycles as they constitute useful intermediates in organic synthesis and are useful dyes (Brock et al., 1999). They are well known in the pharmaceutical industry and have been shown to possess a broad spectrum of biological activities including antiasthmatic activity (Sawada et al., 2004), anti-inflammatory activity (Fokialakis et al., 2002), antimalarial activity (Fossa et al., 2002) and anthelmintic agents (Sakata et al., 1988). We report here the crystal structure of the title compound, (I).
In (I), the benzoquinoline ring system (C1—C5/N1/C18—C25) makes dihedral angles of 61.1 (1) and 39.8 (1)° with the phenyl (C12—C17) and benzene (C6—C11) rings, respectively. The dihedral angle between the phenyl (C12—C17) and benzene (C6—C11) rings is 57.6 (1)°. There is no intermolecular hydrogen bond in the crystal.
For related literature, see: Brock et al. (1999); Fokialakis et al. (2002); Fossa et al. (2002); Sakata et al. (1988); Sawada et al. (2004).
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (please check); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
C25H16BrN | F(000) = 832 |
Mr = 410.30 | Dx = 1.497 Mg m−3 |
Monoclinic, P21/c | Melting point = 478–480 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71070 Å |
a = 12.704 (2) Å | Cell parameters from 6717 reflections |
b = 9.4917 (14) Å | θ = 3.0–25.3° |
c = 15.142 (3) Å | µ = 2.27 mm−1 |
β = 94.612 (4)° | T = 193 K |
V = 1819.9 (5) Å3 | Block, colorless |
Z = 4 | 0.78 × 0.55 × 0.17 mm |
Rigaku Mercury CCD diffractometer | 3336 independent reflections |
Radiation source: fine-focus sealed tube | 3034 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.4°, θmin = 3.0° |
ω scans | h = −15→13 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −11→11 |
Tmin = 0.298, Tmax = 0.679 | l = −18→17 |
17280 measured reflections |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0252P)2 + 1.5016P] where P = (Fo2 + 2Fc2)/3 |
3336 reflections | (Δ/σ)max < 0.001 |
245 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C25H16BrN | V = 1819.9 (5) Å3 |
Mr = 410.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.704 (2) Å | µ = 2.27 mm−1 |
b = 9.4917 (14) Å | T = 193 K |
c = 15.142 (3) Å | 0.78 × 0.55 × 0.17 mm |
β = 94.612 (4)° |
Rigaku Mercury CCD diffractometer | 3336 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 3034 reflections with I > 2σ(I) |
Tmin = 0.298, Tmax = 0.679 | Rint = 0.042 |
17280 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.17 | Δρmax = 0.36 e Å−3 |
3336 reflections | Δρmin = −0.30 e Å−3 |
245 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.41136 (3) | −0.18517 (3) | 0.83655 (2) | 0.04218 (13) | |
N1 | 0.03956 (17) | 0.1754 (2) | 0.57827 (14) | 0.0277 (5) | |
C1 | 0.1407 (2) | 0.1676 (3) | 0.56232 (17) | 0.0257 (6) | |
C2 | 0.1811 (2) | 0.2330 (3) | 0.48741 (17) | 0.0245 (6) | |
C3 | 0.1113 (2) | 0.3102 (3) | 0.43206 (17) | 0.0270 (6) | |
H3 | 0.1367 | 0.3569 | 0.3825 | 0.032* | |
C4 | 0.0041 (2) | 0.3215 (3) | 0.44696 (17) | 0.0247 (6) | |
C5 | −0.0276 (2) | 0.2501 (3) | 0.52243 (17) | 0.0268 (6) | |
C6 | 0.2081 (2) | 0.0849 (3) | 0.62874 (17) | 0.0258 (6) | |
C7 | 0.1673 (2) | −0.0381 (3) | 0.66346 (18) | 0.0294 (6) | |
H7 | 0.0978 | −0.0677 | 0.6438 | 0.035* | |
C8 | 0.2262 (2) | −0.1175 (3) | 0.72588 (18) | 0.0303 (6) | |
H8 | 0.1980 | −0.2012 | 0.7491 | 0.036* | |
C9 | 0.3270 (2) | −0.0729 (3) | 0.75395 (17) | 0.0286 (6) | |
C10 | 0.3691 (2) | 0.0492 (3) | 0.72268 (18) | 0.0304 (6) | |
H10 | 0.4378 | 0.0793 | 0.7438 | 0.036* | |
C11 | 0.3088 (2) | 0.1277 (3) | 0.65955 (17) | 0.0271 (6) | |
H11 | 0.3371 | 0.2119 | 0.6372 | 0.033* | |
C12 | 0.2918 (2) | 0.2181 (3) | 0.46368 (17) | 0.0251 (6) | |
C13 | 0.3338 (2) | 0.0866 (3) | 0.44567 (18) | 0.0312 (7) | |
H13 | 0.2925 | 0.0041 | 0.4513 | 0.037* | |
C14 | 0.4349 (2) | 0.0755 (3) | 0.41985 (19) | 0.0354 (7) | |
H14 | 0.4621 | −0.0145 | 0.4063 | 0.042* | |
C15 | 0.4972 (2) | 0.1933 (3) | 0.41337 (19) | 0.0339 (7) | |
H15 | 0.5674 | 0.1845 | 0.3966 | 0.041* | |
C16 | 0.4569 (2) | 0.3239 (3) | 0.43142 (19) | 0.0331 (7) | |
H16 | 0.4994 | 0.4056 | 0.4275 | 0.040* | |
C17 | 0.3545 (2) | 0.3359 (3) | 0.45528 (18) | 0.0294 (6) | |
H17 | 0.3266 | 0.4266 | 0.4661 | 0.035* | |
C18 | −0.1360 (2) | 0.2552 (3) | 0.54188 (19) | 0.0311 (7) | |
H18 | −0.1573 | 0.2086 | 0.5930 | 0.037* | |
C19 | −0.2081 (2) | 0.3251 (3) | 0.48871 (19) | 0.0325 (7) | |
H19 | −0.2794 | 0.3269 | 0.5031 | 0.039* | |
C20 | −0.1798 (2) | 0.3970 (3) | 0.41076 (18) | 0.0293 (6) | |
C21 | −0.2560 (2) | 0.4670 (3) | 0.35408 (19) | 0.0360 (7) | |
H21 | −0.3274 | 0.4687 | 0.3685 | 0.043* | |
C22 | −0.2291 (3) | 0.5324 (3) | 0.2787 (2) | 0.0408 (8) | |
H22 | −0.2815 | 0.5799 | 0.2415 | 0.049* | |
C23 | −0.1256 (3) | 0.5294 (4) | 0.2567 (2) | 0.0435 (8) | |
H23 | −0.1073 | 0.5736 | 0.2038 | 0.052* | |
C24 | −0.0491 (2) | 0.4632 (3) | 0.3106 (2) | 0.0389 (7) | |
H24 | 0.0217 | 0.4628 | 0.2946 | 0.047* | |
C25 | −0.0736 (2) | 0.3956 (3) | 0.38919 (17) | 0.0276 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0505 (2) | 0.0406 (2) | 0.03533 (19) | 0.01776 (15) | 0.00243 (14) | 0.00900 (15) |
N1 | 0.0279 (13) | 0.0312 (13) | 0.0238 (12) | −0.0001 (10) | 0.0016 (10) | 0.0020 (10) |
C1 | 0.0287 (15) | 0.0247 (14) | 0.0237 (14) | −0.0015 (11) | 0.0011 (12) | −0.0027 (12) |
C2 | 0.0261 (14) | 0.0255 (14) | 0.0219 (14) | −0.0035 (11) | 0.0015 (11) | −0.0030 (11) |
C3 | 0.0311 (15) | 0.0282 (14) | 0.0216 (14) | −0.0030 (12) | 0.0015 (12) | 0.0012 (12) |
C4 | 0.0249 (14) | 0.0258 (14) | 0.0230 (14) | −0.0012 (11) | 0.0004 (11) | −0.0034 (12) |
C5 | 0.0282 (15) | 0.0282 (15) | 0.0236 (14) | −0.0028 (12) | 0.0002 (12) | −0.0031 (12) |
C6 | 0.0305 (15) | 0.0256 (14) | 0.0217 (14) | 0.0043 (12) | 0.0045 (12) | −0.0017 (12) |
C7 | 0.0334 (16) | 0.0292 (15) | 0.0260 (15) | −0.0020 (12) | 0.0042 (12) | −0.0014 (12) |
C8 | 0.0439 (18) | 0.0227 (14) | 0.0254 (15) | 0.0043 (13) | 0.0086 (13) | −0.0001 (12) |
C9 | 0.0340 (16) | 0.0309 (15) | 0.0209 (14) | 0.0113 (13) | 0.0027 (12) | 0.0005 (12) |
C10 | 0.0299 (16) | 0.0349 (16) | 0.0264 (15) | 0.0027 (12) | 0.0025 (12) | −0.0009 (13) |
C11 | 0.0320 (16) | 0.0261 (14) | 0.0233 (14) | −0.0017 (12) | 0.0022 (12) | 0.0021 (12) |
C12 | 0.0252 (14) | 0.0320 (15) | 0.0175 (13) | −0.0002 (12) | −0.0012 (11) | 0.0015 (12) |
C13 | 0.0315 (16) | 0.0310 (16) | 0.0303 (15) | −0.0037 (13) | −0.0029 (13) | −0.0039 (13) |
C14 | 0.0339 (17) | 0.0361 (17) | 0.0360 (17) | 0.0065 (14) | 0.0015 (14) | −0.0086 (14) |
C15 | 0.0244 (15) | 0.0477 (19) | 0.0299 (15) | 0.0039 (14) | 0.0038 (12) | −0.0037 (14) |
C16 | 0.0331 (16) | 0.0351 (17) | 0.0318 (16) | −0.0052 (13) | 0.0070 (13) | 0.0004 (13) |
C17 | 0.0310 (16) | 0.0284 (15) | 0.0294 (15) | 0.0019 (12) | 0.0065 (13) | 0.0007 (12) |
C18 | 0.0293 (16) | 0.0371 (16) | 0.0272 (15) | −0.0006 (13) | 0.0043 (13) | −0.0006 (13) |
C19 | 0.0261 (15) | 0.0397 (17) | 0.0324 (16) | 0.0007 (13) | 0.0068 (13) | −0.0073 (14) |
C20 | 0.0298 (15) | 0.0301 (15) | 0.0273 (15) | 0.0039 (12) | −0.0016 (12) | −0.0083 (13) |
C21 | 0.0328 (16) | 0.0414 (18) | 0.0332 (17) | 0.0085 (14) | −0.0023 (13) | −0.0060 (14) |
C22 | 0.0439 (19) | 0.0441 (19) | 0.0324 (17) | 0.0140 (15) | −0.0098 (14) | −0.0032 (15) |
C23 | 0.044 (2) | 0.050 (2) | 0.0352 (18) | 0.0071 (16) | −0.0035 (15) | 0.0135 (15) |
C24 | 0.0341 (17) | 0.0475 (19) | 0.0349 (17) | −0.0005 (14) | 0.0011 (14) | 0.0095 (15) |
C25 | 0.0286 (15) | 0.0284 (15) | 0.0252 (14) | −0.0003 (12) | −0.0022 (12) | −0.0023 (12) |
Br1—C9 | 1.906 (3) | C13—C14 | 1.376 (4) |
N1—C1 | 1.328 (3) | C13—H13 | 0.9500 |
N1—C5 | 1.353 (3) | C14—C15 | 1.379 (4) |
C1—C2 | 1.424 (4) | C14—H14 | 0.9500 |
C1—C6 | 1.491 (4) | C15—C16 | 1.376 (4) |
C2—C3 | 1.380 (4) | C15—H15 | 0.9500 |
C2—C12 | 1.485 (4) | C16—C17 | 1.383 (4) |
C3—C4 | 1.403 (4) | C16—H16 | 0.9500 |
C3—H3 | 0.9500 | C17—H17 | 0.9500 |
C4—C5 | 1.415 (4) | C18—C19 | 1.344 (4) |
C4—C25 | 1.448 (4) | C18—H18 | 0.9500 |
C5—C18 | 1.432 (4) | C19—C20 | 1.434 (4) |
C6—C11 | 1.387 (4) | C19—H19 | 0.9500 |
C6—C7 | 1.398 (4) | C20—C21 | 1.407 (4) |
C7—C8 | 1.381 (4) | C20—C25 | 1.414 (4) |
C7—H7 | 0.9500 | C21—C22 | 1.366 (4) |
C8—C9 | 1.383 (4) | C21—H21 | 0.9500 |
C8—H8 | 0.9500 | C22—C23 | 1.383 (4) |
C9—C10 | 1.376 (4) | C22—H22 | 0.9500 |
C10—C11 | 1.392 (4) | C23—C24 | 1.370 (4) |
C10—H10 | 0.9500 | C23—H23 | 0.9500 |
C11—H11 | 0.9500 | C24—C25 | 1.409 (4) |
C12—C17 | 1.385 (4) | C24—H24 | 0.9500 |
C12—C13 | 1.393 (4) | ||
C1—N1—C5 | 119.1 (2) | C14—C13—H13 | 119.8 |
N1—C1—C2 | 122.5 (2) | C12—C13—H13 | 119.8 |
N1—C1—C6 | 114.7 (2) | C13—C14—C15 | 120.8 (3) |
C2—C1—C6 | 122.8 (2) | C13—C14—H14 | 119.6 |
C3—C2—C1 | 117.4 (2) | C15—C14—H14 | 119.6 |
C3—C2—C12 | 118.5 (2) | C16—C15—C14 | 119.4 (3) |
C1—C2—C12 | 124.1 (2) | C16—C15—H15 | 120.3 |
C2—C3—C4 | 121.8 (2) | C14—C15—H15 | 120.3 |
C2—C3—H3 | 119.1 | C15—C16—C17 | 119.9 (3) |
C4—C3—H3 | 119.1 | C15—C16—H16 | 120.0 |
C3—C4—C5 | 115.9 (2) | C17—C16—H16 | 120.0 |
C3—C4—C25 | 124.3 (2) | C16—C17—C12 | 121.2 (3) |
C5—C4—C25 | 119.7 (2) | C16—C17—H17 | 119.4 |
N1—C5—C4 | 123.3 (2) | C12—C17—H17 | 119.4 |
N1—C5—C18 | 117.3 (2) | C19—C18—C5 | 120.9 (3) |
C4—C5—C18 | 119.4 (2) | C19—C18—H18 | 119.6 |
C11—C6—C7 | 118.6 (3) | C5—C18—H18 | 119.6 |
C11—C6—C1 | 122.5 (2) | C18—C19—C20 | 121.6 (3) |
C7—C6—C1 | 118.9 (2) | C18—C19—H19 | 119.2 |
C8—C7—C6 | 121.0 (3) | C20—C19—H19 | 119.2 |
C8—C7—H7 | 119.5 | C21—C20—C25 | 119.1 (3) |
C6—C7—H7 | 119.5 | C21—C20—C19 | 121.4 (3) |
C7—C8—C9 | 118.8 (3) | C25—C20—C19 | 119.5 (3) |
C7—C8—H8 | 120.6 | C22—C21—C20 | 121.2 (3) |
C9—C8—H8 | 120.6 | C22—C21—H21 | 119.4 |
C10—C9—C8 | 121.8 (3) | C20—C21—H21 | 119.4 |
C10—C9—Br1 | 118.9 (2) | C21—C22—C23 | 119.8 (3) |
C8—C9—Br1 | 119.3 (2) | C21—C22—H22 | 120.1 |
C9—C10—C11 | 118.7 (3) | C23—C22—H22 | 120.1 |
C9—C10—H10 | 120.7 | C24—C23—C22 | 120.6 (3) |
C11—C10—H10 | 120.7 | C24—C23—H23 | 119.7 |
C6—C11—C10 | 121.1 (3) | C22—C23—H23 | 119.7 |
C6—C11—H11 | 119.5 | C23—C24—C25 | 121.2 (3) |
C10—C11—H11 | 119.5 | C23—C24—H24 | 119.4 |
C17—C12—C13 | 118.2 (2) | C25—C24—H24 | 119.4 |
C17—C12—C2 | 120.5 (2) | C24—C25—C20 | 118.1 (3) |
C13—C12—C2 | 121.2 (2) | C24—C25—C4 | 123.1 (3) |
C14—C13—C12 | 120.4 (3) | C20—C25—C4 | 118.8 (2) |
C5—N1—C1—C2 | −1.2 (4) | C1—C2—C12—C17 | −122.9 (3) |
C5—N1—C1—C6 | 179.0 (2) | C3—C2—C12—C13 | −117.5 (3) |
N1—C1—C2—C3 | 2.1 (4) | C1—C2—C12—C13 | 59.9 (4) |
C6—C1—C2—C3 | −178.2 (2) | C17—C12—C13—C14 | −0.3 (4) |
N1—C1—C2—C12 | −175.3 (2) | C2—C12—C13—C14 | 177.0 (3) |
C6—C1—C2—C12 | 4.4 (4) | C12—C13—C14—C15 | 1.6 (4) |
C1—C2—C3—C4 | −1.7 (4) | C13—C14—C15—C16 | −1.2 (4) |
C12—C2—C3—C4 | 175.9 (2) | C14—C15—C16—C17 | −0.4 (4) |
C2—C3—C4—C5 | 0.5 (4) | C15—C16—C17—C12 | 1.7 (4) |
C2—C3—C4—C25 | −177.1 (3) | C13—C12—C17—C16 | −1.3 (4) |
C1—N1—C5—C4 | 0.0 (4) | C2—C12—C17—C16 | −178.6 (2) |
C1—N1—C5—C18 | 179.7 (2) | N1—C5—C18—C19 | −178.8 (3) |
C3—C4—C5—N1 | 0.4 (4) | C4—C5—C18—C19 | 1.0 (4) |
C25—C4—C5—N1 | 178.2 (2) | C5—C18—C19—C20 | 0.1 (4) |
C3—C4—C5—C18 | −179.4 (2) | C18—C19—C20—C21 | 178.3 (3) |
C25—C4—C5—C18 | −1.6 (4) | C18—C19—C20—C25 | −0.4 (4) |
N1—C1—C6—C11 | −138.9 (3) | C25—C20—C21—C22 | 0.4 (4) |
C2—C1—C6—C11 | 41.3 (4) | C19—C20—C21—C22 | −178.4 (3) |
N1—C1—C6—C7 | 39.0 (3) | C20—C21—C22—C23 | 0.6 (5) |
C2—C1—C6—C7 | −140.8 (3) | C21—C22—C23—C24 | −1.1 (5) |
C11—C6—C7—C8 | −1.2 (4) | C22—C23—C24—C25 | 0.5 (5) |
C1—C6—C7—C8 | −179.3 (2) | C23—C24—C25—C20 | 0.5 (4) |
C6—C7—C8—C9 | 0.2 (4) | C23—C24—C25—C4 | 178.5 (3) |
C7—C8—C9—C10 | 1.2 (4) | C21—C20—C25—C24 | −0.9 (4) |
C7—C8—C9—Br1 | −177.56 (19) | C19—C20—C25—C24 | 177.9 (3) |
C8—C9—C10—C11 | −1.5 (4) | C21—C20—C25—C4 | −179.0 (2) |
Br1—C9—C10—C11 | 177.3 (2) | C19—C20—C25—C4 | −0.2 (4) |
C7—C6—C11—C10 | 1.0 (4) | C3—C4—C25—C24 | 0.8 (4) |
C1—C6—C11—C10 | 178.9 (2) | C5—C4—C25—C24 | −176.8 (3) |
C9—C10—C11—C6 | 0.4 (4) | C3—C4—C25—C20 | 178.8 (3) |
C3—C2—C12—C17 | 59.8 (3) | C5—C4—C25—C20 | 1.2 (4) |
Experimental details
Crystal data | |
Chemical formula | C25H16BrN |
Mr | 410.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 193 |
a, b, c (Å) | 12.704 (2), 9.4917 (14), 15.142 (3) |
β (°) | 94.612 (4) |
V (Å3) | 1819.9 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.27 |
Crystal size (mm) | 0.78 × 0.55 × 0.17 |
Data collection | |
Diffractometer | Rigaku Mercury CCD |
Absorption correction | Multi-scan (Jacobson, 1998) |
Tmin, Tmax | 0.298, 0.679 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17280, 3336, 3034 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.084, 1.17 |
No. of reflections | 3336 |
No. of parameters | 245 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.30 |
Computer programs: CrystalClear (Rigaku, 1999), CrystalClear, CrystalStructure (Rigaku/MSC 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97 (please check), SHELXL97.
Quinoline and its derivatives represent an important class of nitrogen-containing heterocycles as they constitute useful intermediates in organic synthesis and are useful dyes (Brock et al., 1999). They are well known in the pharmaceutical industry and have been shown to possess a broad spectrum of biological activities including antiasthmatic activity (Sawada et al., 2004), anti-inflammatory activity (Fokialakis et al., 2002), antimalarial activity (Fossa et al., 2002) and anthelmintic agents (Sakata et al., 1988). We report here the crystal structure of the title compound, (I).
In (I), the benzoquinoline ring system (C1—C5/N1/C18—C25) makes dihedral angles of 61.1 (1) and 39.8 (1)° with the phenyl (C12—C17) and benzene (C6—C11) rings, respectively. The dihedral angle between the phenyl (C12—C17) and benzene (C6—C11) rings is 57.6 (1)°. There is no intermolecular hydrogen bond in the crystal.