Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705369X/sj2391sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705369X/sj2391Isup2.hkl |
CCDC reference: 672799
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.050
- wR factor = 0.110
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br2 .. 3.55 Ang.
Alert level G 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 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 1 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
2-Chloro-N,N-diphenylacetamide was prepared by the reaction of diphenylamine and chloroacetyl chloride in the presence of triethylamine, according to the literature method of Wen et al. (2005). To a solution of 5,7-dibromo-8-hydroxyquinoline (3.02 g, 10 mmol) in acetone (60 ml) were added 2-chloro-N,N-diphenylacetamide (2.45 g,10 mmol), K2CO3 (1.52 g, 11 mmol) and KI (0.5 g), and the resulting mixture was stirred at 333 K for 5 h. After cooling to room temperature, the mixture was washed three times with water and filtered. Colourless single crystals of (I) suitable for an X-ray diffraction study were obtained by slow evaporation of an ethanol-DMF (1:1 v/v) solution over a period of 15 d.
All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C23H16Br2N2O2 | F(000) = 1016 |
Mr = 512.18 | Dx = 1.670 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1172 reflections |
a = 10.1223 (12) Å | θ = 2.9–20.3° |
b = 9.6013 (11) Å | µ = 4.00 mm−1 |
c = 21.003 (3) Å | T = 293 K |
β = 93.826 (2)° | Block, colourless |
V = 2036.7 (4) Å3 | 0.17 × 0.13 × 0.10 mm |
Z = 4 |
Siemens SMART 1000 CCD area-detector diffractometer | 3731 independent reflections |
Radiation source: fine-focus sealed tube | 2346 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.066 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.4°, θmin = 1.9° |
ω scans | h = −12→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −7→11 |
Tmin = 0.549, Tmax = 0.690 | l = −25→25 |
10474 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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0474P)2] where P = (Fo2 + 2Fc2)/3 |
3731 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
C23H16Br2N2O2 | V = 2036.7 (4) Å3 |
Mr = 512.18 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.1223 (12) Å | µ = 4.00 mm−1 |
b = 9.6013 (11) Å | T = 293 K |
c = 21.003 (3) Å | 0.17 × 0.13 × 0.10 mm |
β = 93.826 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 3731 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2346 reflections with I > 2σ(I) |
Tmin = 0.549, Tmax = 0.690 | Rint = 0.066 |
10474 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.92 e Å−3 |
3731 reflections | Δρmin = −0.57 e Å−3 |
262 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 | 0.32777 (6) | 0.08638 (7) | 0.20333 (3) | 0.0431 (2) | |
Br2 | −0.07694 (6) | 0.48192 (6) | 0.17923 (3) | 0.0484 (2) | |
O1 | 0.2377 (3) | 0.0119 (4) | 0.06982 (16) | 0.0322 (9) | |
N2 | 0.3683 (4) | 0.1452 (4) | −0.07504 (19) | 0.0279 (10) | |
C11 | 0.3618 (5) | 0.1175 (6) | −0.0113 (2) | 0.0292 (13) | |
C9 | 0.1699 (5) | 0.1282 (6) | 0.0876 (2) | 0.0297 (13) | |
C19 | 0.3447 (5) | −0.0735 (6) | −0.1338 (2) | 0.0352 (14) | |
H19A | 0.4155 | −0.1102 | −0.1087 | 0.042* | |
C10 | 0.2784 (5) | −0.0065 (5) | 0.0065 (2) | 0.0308 (13) | |
H10A | 0.2012 | −0.0144 | −0.0232 | 0.037* | |
H10B | 0.3297 | −0.0915 | 0.0042 | 0.037* | |
O2 | 0.4198 (4) | 0.1870 (4) | 0.03023 (17) | 0.0381 (10) | |
C2 | 0.1211 (5) | 0.2776 (5) | 0.1766 (3) | 0.0344 (14) | |
H2A | 0.1388 | 0.3034 | 0.2190 | 0.041* | |
C1 | 0.1932 (5) | 0.1694 (5) | 0.1497 (2) | 0.0295 (13) | |
C18 | 0.3034 (5) | 0.0620 (6) | −0.1244 (2) | 0.0274 (13) | |
C12 | 0.4366 (5) | 0.2706 (5) | −0.0935 (2) | 0.0267 (12) | |
C8 | 0.0732 (5) | 0.2001 (6) | 0.0481 (3) | 0.0296 (13) | |
C4 | −0.0027 (5) | 0.3077 (6) | 0.0750 (3) | 0.0339 (13) | |
N1 | 0.0543 (5) | 0.1642 (5) | −0.0144 (2) | 0.0392 (12) | |
C3 | 0.0256 (5) | 0.3436 (5) | 0.1397 (3) | 0.0350 (14) | |
C23 | 0.1990 (5) | 0.1175 (6) | −0.1627 (3) | 0.0372 (14) | |
H23A | 0.1719 | 0.2088 | −0.1567 | 0.045* | |
C20 | 0.2799 (6) | −0.1541 (6) | −0.1809 (3) | 0.0414 (15) | |
H20A | 0.3070 | −0.2454 | −0.1873 | 0.050* | |
C13 | 0.5378 (5) | 0.2598 (6) | −0.1340 (3) | 0.0381 (15) | |
H13A | 0.5625 | 0.1734 | −0.1493 | 0.046* | |
C16 | 0.4666 (7) | 0.5170 (6) | −0.0880 (3) | 0.0561 (19) | |
H16A | 0.4421 | 0.6035 | −0.0727 | 0.067* | |
C5 | −0.1016 (5) | 0.3726 (6) | 0.0342 (3) | 0.0451 (16) | |
H5A | −0.1544 | 0.4420 | 0.0501 | 0.054* | |
C7 | −0.0373 (6) | 0.2291 (7) | −0.0504 (3) | 0.0487 (17) | |
H7A | −0.0486 | 0.2046 | −0.0932 | 0.058* | |
C17 | 0.4011 (6) | 0.3991 (6) | −0.0702 (3) | 0.0418 (15) | |
H17A | 0.3333 | 0.4058 | −0.0426 | 0.050* | |
C6 | −0.1195 (6) | 0.3344 (7) | −0.0274 (3) | 0.0497 (17) | |
H6A | −0.1846 | 0.3764 | −0.0543 | 0.060* | |
C14 | 0.6021 (6) | 0.3799 (8) | −0.1516 (3) | 0.0540 (19) | |
H14A | 0.6695 | 0.3743 | −0.1795 | 0.065* | |
C15 | 0.5668 (7) | 0.5078 (7) | −0.1280 (3) | 0.0539 (19) | |
H15A | 0.6115 | 0.5877 | −0.1393 | 0.065* | |
C21 | 0.1755 (6) | −0.0993 (7) | −0.2184 (3) | 0.0440 (16) | |
H21A | 0.1318 | −0.1542 | −0.2496 | 0.053* | |
C22 | 0.1357 (6) | 0.0358 (7) | −0.2099 (3) | 0.0438 (16) | |
H22A | 0.0661 | 0.0725 | −0.2358 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0501 (4) | 0.0464 (4) | 0.0326 (3) | 0.0204 (3) | 0.0024 (3) | 0.0026 (3) |
Br2 | 0.0444 (4) | 0.0339 (4) | 0.0667 (5) | 0.0125 (3) | 0.0013 (3) | −0.0111 (3) |
O1 | 0.044 (2) | 0.022 (2) | 0.031 (2) | 0.0046 (18) | 0.0090 (18) | 0.0023 (17) |
N2 | 0.038 (3) | 0.020 (2) | 0.025 (2) | −0.003 (2) | 0.000 (2) | 0.000 (2) |
C11 | 0.034 (3) | 0.027 (3) | 0.026 (3) | 0.002 (3) | 0.001 (3) | 0.002 (3) |
C9 | 0.032 (3) | 0.025 (3) | 0.033 (3) | 0.000 (3) | 0.005 (3) | 0.003 (3) |
C19 | 0.043 (3) | 0.026 (3) | 0.037 (3) | 0.003 (3) | 0.005 (3) | 0.002 (3) |
C10 | 0.042 (3) | 0.024 (3) | 0.027 (3) | −0.002 (3) | 0.010 (3) | 0.000 (2) |
O2 | 0.051 (2) | 0.032 (2) | 0.031 (2) | −0.009 (2) | −0.0028 (19) | −0.0022 (19) |
C2 | 0.039 (3) | 0.025 (3) | 0.041 (3) | 0.000 (3) | 0.008 (3) | 0.002 (3) |
C1 | 0.036 (3) | 0.022 (3) | 0.031 (3) | 0.003 (3) | 0.003 (2) | 0.008 (2) |
C18 | 0.033 (3) | 0.027 (3) | 0.022 (3) | −0.006 (3) | 0.003 (2) | −0.002 (2) |
C12 | 0.028 (3) | 0.021 (3) | 0.030 (3) | −0.006 (3) | −0.004 (2) | 0.003 (2) |
C8 | 0.025 (3) | 0.026 (3) | 0.037 (3) | −0.009 (3) | −0.001 (2) | 0.007 (3) |
C4 | 0.028 (3) | 0.028 (3) | 0.046 (4) | −0.002 (3) | 0.000 (3) | 0.002 (3) |
N1 | 0.046 (3) | 0.034 (3) | 0.036 (3) | −0.002 (3) | −0.006 (2) | 0.002 (2) |
C3 | 0.030 (3) | 0.020 (3) | 0.055 (4) | −0.001 (3) | 0.008 (3) | −0.002 (3) |
C23 | 0.044 (3) | 0.027 (3) | 0.041 (3) | 0.001 (3) | 0.006 (3) | 0.003 (3) |
C20 | 0.053 (4) | 0.028 (3) | 0.044 (4) | −0.008 (3) | 0.012 (3) | −0.014 (3) |
C13 | 0.034 (3) | 0.045 (4) | 0.036 (3) | −0.001 (3) | 0.005 (3) | −0.003 (3) |
C16 | 0.086 (5) | 0.018 (3) | 0.062 (5) | −0.008 (4) | −0.013 (4) | 0.003 (3) |
C5 | 0.040 (4) | 0.037 (4) | 0.057 (4) | 0.004 (3) | −0.008 (3) | 0.006 (3) |
C7 | 0.048 (4) | 0.046 (4) | 0.050 (4) | −0.015 (4) | −0.007 (3) | 0.008 (3) |
C17 | 0.047 (4) | 0.028 (3) | 0.051 (4) | 0.006 (3) | 0.005 (3) | −0.003 (3) |
C6 | 0.044 (4) | 0.047 (4) | 0.055 (4) | 0.001 (3) | −0.014 (3) | 0.015 (4) |
C14 | 0.048 (4) | 0.072 (5) | 0.043 (4) | −0.027 (4) | 0.006 (3) | 0.007 (4) |
C15 | 0.072 (5) | 0.042 (4) | 0.045 (4) | −0.030 (4) | −0.023 (4) | 0.018 (3) |
C21 | 0.048 (4) | 0.045 (4) | 0.040 (4) | −0.017 (3) | 0.005 (3) | −0.004 (3) |
C22 | 0.039 (4) | 0.049 (4) | 0.041 (4) | −0.001 (3) | −0.012 (3) | 0.015 (3) |
Br1—C1 | 1.885 (5) | C4—C3 | 1.413 (7) |
Br2—C3 | 1.909 (5) | C4—C5 | 1.419 (7) |
O1—C9 | 1.376 (6) | N1—C7 | 1.314 (7) |
O1—C10 | 1.429 (5) | C23—C22 | 1.387 (8) |
N2—C11 | 1.370 (6) | C23—H23A | 0.9300 |
N2—C18 | 1.433 (6) | C20—C21 | 1.379 (8) |
N2—C12 | 1.453 (6) | C20—H20A | 0.9300 |
C11—O2 | 1.218 (6) | C13—C14 | 1.386 (8) |
C11—C10 | 1.521 (7) | C13—H13A | 0.9300 |
C9—C1 | 1.369 (7) | C16—C15 | 1.362 (9) |
C9—C8 | 1.420 (7) | C16—C17 | 1.376 (8) |
C19—C18 | 1.385 (7) | C16—H16A | 0.9300 |
C19—C20 | 1.386 (7) | C5—C6 | 1.345 (8) |
C19—H19A | 0.9300 | C5—H5A | 0.9300 |
C10—H10A | 0.9700 | C7—C6 | 1.415 (8) |
C10—H10B | 0.9700 | C7—H7A | 0.9300 |
C2—C3 | 1.355 (7) | C17—H17A | 0.9300 |
C2—C1 | 1.410 (7) | C6—H6A | 0.9300 |
C2—H2A | 0.9300 | C14—C15 | 1.380 (9) |
C18—C23 | 1.391 (7) | C14—H14A | 0.9300 |
C12—C13 | 1.379 (7) | C15—H15A | 0.9300 |
C12—C17 | 1.383 (7) | C21—C22 | 1.373 (8) |
C8—N1 | 1.358 (6) | C21—H21A | 0.9300 |
C8—C4 | 1.426 (7) | C22—H22A | 0.9300 |
C9—O1—C10 | 122.2 (4) | C2—C3—Br2 | 117.7 (4) |
C11—N2—C18 | 123.3 (4) | C4—C3—Br2 | 120.5 (4) |
C11—N2—C12 | 118.4 (4) | C22—C23—C18 | 119.6 (5) |
C18—N2—C12 | 118.2 (4) | C22—C23—H23A | 120.2 |
O2—C11—N2 | 122.8 (5) | C18—C23—H23A | 120.2 |
O2—C11—C10 | 120.1 (5) | C21—C20—C19 | 120.1 (6) |
N2—C11—C10 | 117.1 (5) | C21—C20—H20A | 119.9 |
C1—C9—O1 | 115.8 (5) | C19—C20—H20A | 119.9 |
C1—C9—C8 | 119.0 (5) | C12—C13—C14 | 119.0 (6) |
O1—C9—C8 | 125.0 (5) | C12—C13—H13A | 120.5 |
C18—C19—C20 | 119.6 (5) | C14—C13—H13A | 120.5 |
C18—C19—H19A | 120.2 | C15—C16—C17 | 120.4 (6) |
C20—C19—H19A | 120.2 | C15—C16—H16A | 119.8 |
O1—C10—C11 | 109.4 (4) | C17—C16—H16A | 119.8 |
O1—C10—H10A | 109.8 | C6—C5—C4 | 120.4 (6) |
C11—C10—H10A | 109.8 | C6—C5—H5A | 119.8 |
O1—C10—H10B | 109.8 | C4—C5—H5A | 119.8 |
C11—C10—H10B | 109.8 | N1—C7—C6 | 123.5 (6) |
H10A—C10—H10B | 108.2 | N1—C7—H7A | 118.3 |
C3—C2—C1 | 119.0 (5) | C6—C7—H7A | 118.3 |
C3—C2—H2A | 120.5 | C16—C17—C12 | 119.8 (6) |
C1—C2—H2A | 120.5 | C16—C17—H17A | 120.1 |
C9—C1—C2 | 122.3 (5) | C12—C17—H17A | 120.1 |
C9—C1—Br1 | 121.3 (4) | C5—C6—C7 | 118.5 (6) |
C2—C1—Br1 | 116.4 (4) | C5—C6—H6A | 120.7 |
C19—C18—C23 | 120.1 (5) | C7—C6—H6A | 120.7 |
C19—C18—N2 | 120.0 (5) | C15—C14—C13 | 120.4 (6) |
C23—C18—N2 | 119.9 (5) | C15—C14—H14A | 119.8 |
C13—C12—C17 | 120.4 (5) | C13—C14—H14A | 119.8 |
C13—C12—N2 | 119.3 (5) | C16—C15—C14 | 120.0 (6) |
C17—C12—N2 | 120.3 (5) | C16—C15—H15A | 120.0 |
N1—C8—C9 | 119.2 (5) | C14—C15—H15A | 120.0 |
N1—C8—C4 | 121.5 (5) | C22—C21—C20 | 120.5 (6) |
C9—C8—C4 | 119.3 (5) | C22—C21—H21A | 119.8 |
C3—C4—C5 | 124.3 (5) | C20—C21—H21A | 119.8 |
C3—C4—C8 | 118.6 (5) | C21—C22—C23 | 120.1 (5) |
C5—C4—C8 | 117.1 (5) | C21—C22—H22A | 120.0 |
C7—N1—C8 | 119.0 (5) | C23—C22—H22A | 120.0 |
C2—C3—C4 | 121.8 (5) | ||
C18—N2—C11—O2 | 178.2 (5) | C9—C8—C4—C3 | 3.0 (7) |
C12—N2—C11—O2 | −6.1 (7) | N1—C8—C4—C5 | 1.9 (8) |
C18—N2—C11—C10 | −1.4 (7) | C9—C8—C4—C5 | −177.6 (5) |
C12—N2—C11—C10 | 174.2 (4) | C9—C8—N1—C7 | 178.6 (5) |
C10—O1—C9—C1 | −148.4 (5) | C4—C8—N1—C7 | −0.9 (8) |
C10—O1—C9—C8 | 36.2 (7) | C1—C2—C3—C4 | −0.6 (8) |
C9—O1—C10—C11 | 55.7 (6) | C1—C2—C3—Br2 | 176.3 (4) |
O2—C11—C10—O1 | 24.0 (7) | C5—C4—C3—C2 | 179.8 (5) |
N2—C11—C10—O1 | −156.3 (4) | C8—C4—C3—C2 | −0.8 (8) |
O1—C9—C1—C2 | −173.3 (4) | C5—C4—C3—Br2 | 2.9 (7) |
C8—C9—C1—C2 | 2.4 (8) | C8—C4—C3—Br2 | −177.7 (4) |
O1—C9—C1—Br1 | 8.4 (7) | C19—C18—C23—C22 | 0.8 (8) |
C8—C9—C1—Br1 | −175.9 (4) | N2—C18—C23—C22 | −179.2 (5) |
C3—C2—C1—C9 | −0.2 (8) | C18—C19—C20—C21 | 0.4 (8) |
C3—C2—C1—Br1 | 178.2 (4) | C17—C12—C13—C14 | −0.8 (8) |
C20—C19—C18—C23 | −1.1 (8) | N2—C12—C13—C14 | 179.7 (5) |
C20—C19—C18—N2 | 178.9 (5) | C3—C4—C5—C6 | 178.2 (5) |
C11—N2—C18—C19 | −67.1 (7) | C8—C4—C5—C6 | −1.2 (8) |
C12—N2—C18—C19 | 117.3 (5) | C8—N1—C7—C6 | −0.8 (8) |
C11—N2—C18—C23 | 112.9 (6) | C15—C16—C17—C12 | −0.6 (9) |
C12—N2—C18—C23 | −62.7 (6) | C13—C12—C17—C16 | 0.5 (8) |
C11—N2—C12—C13 | 125.1 (5) | N2—C12—C17—C16 | −180.0 (5) |
C18—N2—C12—C13 | −59.0 (6) | C4—C5—C6—C7 | −0.4 (9) |
C11—N2—C12—C17 | −54.4 (7) | N1—C7—C6—C5 | 1.5 (9) |
C18—N2—C12—C17 | 121.5 (5) | C12—C13—C14—C15 | 1.1 (9) |
C1—C9—C8—N1 | 176.8 (5) | C17—C16—C15—C14 | 1.0 (9) |
O1—C9—C8—N1 | −8.0 (8) | C13—C14—C15—C16 | −1.2 (9) |
C1—C9—C8—C4 | −3.7 (7) | C19—C20—C21—C22 | 0.7 (8) |
O1—C9—C8—C4 | 171.5 (5) | C20—C21—C22—C23 | −1.0 (9) |
N1—C8—C4—C3 | −177.5 (5) | C18—C23—C22—C21 | 0.3 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···Br2 | 0.93 | 2.80 | 3.216 (6) | 108 |
C10—H10A···N1 | 0.97 | 2.29 | 2.809 (7) | 113 |
C16—H16A···O2i | 0.93 | 2.58 | 3.269 (7) | 132 |
C19—H19A···O2ii | 0.93 | 2.38 | 3.303 (6) | 171 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C23H16Br2N2O2 |
Mr | 512.18 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 10.1223 (12), 9.6013 (11), 21.003 (3) |
β (°) | 93.826 (2) |
V (Å3) | 2036.7 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.00 |
Crystal size (mm) | 0.17 × 0.13 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.549, 0.690 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10474, 3731, 2346 |
Rint | 0.066 |
(sin θ/λ)max (Å−1) | 0.603 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.110, 0.96 |
No. of reflections | 3731 |
No. of parameters | 262 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.92, −0.57 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···Br2 | 0.93 | 2.799 | 3.216 (6) | 108.39 |
C10—H10A···N1 | 0.97 | 2.285 | 2.809 (7) | 112.96 |
C16—H16A···O2i | 0.93 | 2.575 | 3.269 (7) | 131.77 |
C19—H19A···O2ii | 0.93 | 2.382 | 3.303 (6) | 170.64 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z. |
8-Hydroxyquinoline and its derivatives have found extensive applications as analytical reagents, e.g. in absorption spectrophotometry, fluorimetry, solvent extraction and partition chromatography, due to their ability to form stable complexes with many metallic ions (Bratzel et al., 1972). Some 8-hydroxyquinoline derivatives and their complexes with transition metals demonstrate antibacterial activity (Patel & Patel, 1999). Recently, structures of unsubstituted 8-hydroxyquinolinate amide-type compounds, namely, N-phenyl-2-(quinolin-8-yloxy)acetamide, (II) (Li et al., 2005) and N,N-diphenyl-2-(quinolin-8-yloxy)acetamide, (III) (Wen et al., 2005) have been reported. In a continuation of our search for suitable reagents to use in the extraction of metal ions, fluorescent materials and analytical reagents, we prepared the title compound, (I) (Fig. 1), a new amide-based 5,7-dibromo-8-hydroxyquinoline derivative, and we report its crystal structure here.
In the title compound, the bond lengths and angles are within normal ranges (Allen et al., 1987). The quinoline fragment is essentially planar, with a dihedral angle of 2.0 (3)° between the benzene (C1–C4/C8/C9) ring and pyridine (N1/C4–C8) ring. The quinoline mean plane makes dihedral angles of 81.6 (2)° and 31.2 (2)°, with C12–C17 and C18–C23 benzene rings, respectively, while the dihedral angle between the latter two aromatic rings is 82.4 (3)°. Intramolecular C5—H5A···Br2 and C10—H10A···N1 hydrogen bonds (Fig.1 and Table 1), form two five-numbered rings and affect the conformation of the molecule.
In the crystal structure, molecules are linked into chains along the b axis (Fig. 2) by intermolecular C16—H16A···O2 and C19—H19A···O2 hydrogen bonds(Fig. 2 and Table 1).