Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034228/hg2255sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034228/hg2255Isup2.hkl |
CCDC reference: 657790
Key indicators
- Single-crystal X-ray study
- T = 295 K
- R factor = 0.038
- wR factor = 0.099
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
5-Bromo-2-hyoxybenzophenone (47 g, 0.17 mol), diaminobenzene (18.4 g, 0.17 mol), piperidine (15 g, 0.18 mol) and triethylorthoformate (20 ml) were refluxed in absolute methanol (150 ml) until crystals started to appear. The solution was cooled to room temperature and the desired compound was collected by filtration. Single crystals suitable for X-ray measurements were obtained by slow evaporation of chloroform/ ethanol (1:1 v/v) at room temperature.
H atoms except H1 were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93Å and N—H = 0.86 Å, and with Uiso(H)=1.2Ueq(C). H1 wass located from a delta(F) map.
Monocondensed Schiff bases are attractive because of their use as intermediates in the synthesis of unsymmetrical multidentate Schiff base ligands. Schiff bases also serve as potential chelating agents and possess biological activities (Yang, 2006). Transition metal complexes derived from Schiff bases are are of great interest since they exhibit numerous biological activities such as antitumor (Ranford et al., 1993), anti-candida (Majella et al., 1999), antimicrobacterial (Saha et al., 2004) and antimicrobial (Zoroddu et al., 1996) activities. In this paper, we have synthesized a new Schiff base compound by the condensation of 5-Bromo 2-hyoxybenzophenone with diaminobenzene and characterized it with X-ray crystallographic techniques.
All the bond lengths in the compounds are within normal ranges (Allen et al., 1987). The C7—N2 bond length of 1.281 (3)Å confirms it as a double bond. The C—Br bond length [1.887 (3) Å] is agreement with other reported bonds [1.884 (2)Å (Wiktor et al., 2000)].
Four atoms C4,C7,C8,N2 are in a plane (p1). The benzene ring, C8—C13, (p3), is approximately planar with its immediate substituent atoms Br1, O1, and C7, with a maximum deviation of 0.028 (1)Å for O1. The benzene ring, C14—C19, is planar with its immediate substituent atoms N1 forming the plane p4. The dihedral angles formed by p1 with the benzene ring, C1—C6, (p2), p3 and p4 are 56.5 (2), 6.2 (4) and 55.7 (1)°, respectively. The dihedral angles formed by p2 with p3 and p4 are 59.4 (2) and 61.8 (3)°. The dihedral angle between p3 and p4 is 61.8 (2)°.
The molecular structure is stabilized by intramolecular C—H···π interactions and O—H···N, N—H···O and N—H···N inter- and intra-molecular hydrogen-bond interactions [N1···Cg1 = 3.799 (2), H1B···Cg1 = 3.200 (1) Å, N1—H1B···Cg1 = 128.8 (3)° (Symmetry code: 1 - x,2 - y,-z); C1···Cg3 = 3.557 (3), H1C···Cg3 = 2.758 (2) Å, C1—H1C···Cg3 = 144.6 (2)° (Symmetry code: 1 + x,y,z); C19···Cg2 = 3.800 (3), H19A···Cg2 = 2.977 (2) Å, C19—H19A···Cg2 = 148.3 (2)° (Symmetry code: 1 - x,1 - y,-z). Cg1, Cg2 and Cg3 are the centroids of phenyl rings C1—C6, C8—C13 and C14—C19, respectively]. Hydrogen-bond interactions are list in Table 2.
For related literature, see: Allen et al. (1987); Majella et al. (1999); Ranford & Sadler (1993); Saha et al. (2004); Wiktor et al. (2000); Yang (2006); Zoroddu et al. (1996).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
C19H15BrN2O | Z = 2 |
Mr = 367.23 | F(000) = 372 |
Triclinic, P1 | Dx = 1.505 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4504 (17) Å | Cell parameters from 25 reflections |
b = 9.4206 (19) Å | θ = 4–14° |
c = 11.141 (2) Å | µ = 2.54 mm−1 |
α = 68.94 (3)° | T = 295 K |
β = 85.40 (3)° | Block, colorless |
γ = 78.31 (3)° | 0.20 × 0.20 × 0.18 mm |
V = 810.5 (3) Å3 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.018 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.0° |
Graphite monochromator | h = −9→10 |
ω scans | k = −11→6 |
3365 measured reflections | l = −13→12 |
2785 independent reflections | 3 standard reflections every 100 reflections |
2094 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3 |
2785 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C19H15BrN2O | γ = 78.31 (3)° |
Mr = 367.23 | V = 810.5 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.4504 (17) Å | Mo Kα radiation |
b = 9.4206 (19) Å | µ = 2.54 mm−1 |
c = 11.141 (2) Å | T = 295 K |
α = 68.94 (3)° | 0.20 × 0.20 × 0.18 mm |
β = 85.40 (3)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.018 |
3365 measured reflections | 3 standard reflections every 100 reflections |
2785 independent reflections | intensity decay: none |
2094 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.38 e Å−3 |
2785 reflections | Δρmin = −0.28 e Å−3 |
208 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 | 0.82601 (5) | 0.79635 (4) | −0.41528 (3) | 0.07530 (19) | |
O1 | 0.1888 (2) | 0.8105 (2) | −0.1436 (2) | 0.0624 (6) | |
H1 | 0.2000 | 0.7754 | −0.0624 | 0.075* | |
N1 | 0.1382 (3) | 0.9926 (3) | 0.1374 (3) | 0.0688 (8) | |
H1A | 0.1667 | 1.0127 | 0.0581 | 0.083* | |
H1B | 0.0732 | 1.0614 | 0.1604 | 0.083* | |
N2 | 0.3303 (3) | 0.7716 (3) | 0.0581 (2) | 0.0517 (6) | |
C1 | 0.9008 (5) | 0.6305 (5) | 0.2237 (4) | 0.0752 (10) | |
H1C | 0.9945 | 0.6028 | 0.2716 | 0.090* | |
C2 | 0.8721 (4) | 0.5433 (4) | 0.1568 (3) | 0.0674 (9) | |
H2B | 0.9468 | 0.4547 | 0.1601 | 0.081* | |
C3 | 0.7361 (4) | 0.5825 (4) | 0.0847 (3) | 0.0554 (8) | |
H3A | 0.7197 | 0.5218 | 0.0386 | 0.066* | |
C4 | 0.6232 (4) | 0.7126 (3) | 0.0804 (3) | 0.0454 (7) | |
C5 | 0.6508 (4) | 0.8013 (4) | 0.1486 (3) | 0.0559 (8) | |
H5A | 0.5755 | 0.8891 | 0.1468 | 0.067* | |
C6 | 0.7894 (5) | 0.7604 (5) | 0.2197 (3) | 0.0708 (10) | |
H6A | 0.8078 | 0.8211 | 0.2652 | 0.085* | |
C7 | 0.4709 (3) | 0.7531 (3) | 0.0073 (3) | 0.0441 (7) | |
C8 | 0.4763 (3) | 0.7798 (3) | −0.1316 (3) | 0.0449 (7) | |
C9 | 0.6214 (4) | 0.7812 (3) | −0.1996 (3) | 0.0518 (7) | |
H9A | 0.7169 | 0.7688 | −0.1577 | 0.062* | |
C10 | 0.6255 (4) | 0.8009 (3) | −0.3276 (3) | 0.0552 (8) | |
C11 | 0.4869 (4) | 0.8210 (4) | −0.3928 (3) | 0.0601 (9) | |
H11A | 0.4913 | 0.8332 | −0.4796 | 0.072* | |
C12 | 0.3429 (4) | 0.8230 (4) | −0.3288 (3) | 0.0591 (8) | |
H12A | 0.2485 | 0.8371 | −0.3727 | 0.071* | |
C13 | 0.3342 (4) | 0.8041 (3) | −0.1989 (3) | 0.0500 (7) | |
C14 | 0.3017 (3) | 0.7385 (3) | 0.1922 (3) | 0.0478 (7) | |
C15 | 0.1967 (3) | 0.8507 (4) | 0.2275 (3) | 0.0505 (7) | |
C16 | 0.1562 (4) | 0.8156 (4) | 0.3567 (3) | 0.0607 (9) | |
H16A | 0.0891 | 0.8903 | 0.3833 | 0.073* | |
C17 | 0.2127 (4) | 0.6739 (4) | 0.4455 (3) | 0.0657 (9) | |
H17A | 0.1807 | 0.6521 | 0.5310 | 0.079* | |
C18 | 0.3161 (4) | 0.5631 (4) | 0.4103 (3) | 0.0646 (9) | |
H18A | 0.3555 | 0.4669 | 0.4713 | 0.078* | |
C19 | 0.3607 (4) | 0.5967 (4) | 0.2831 (3) | 0.0585 (8) | |
H19A | 0.4316 | 0.5227 | 0.2581 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0749 (3) | 0.0860 (3) | 0.0579 (2) | −0.0128 (2) | 0.01688 (19) | −0.0216 (2) |
O1 | 0.0479 (13) | 0.0774 (16) | 0.0585 (13) | 0.0055 (11) | −0.0083 (11) | −0.0275 (12) |
N1 | 0.0678 (19) | 0.0588 (17) | 0.0656 (18) | 0.0057 (14) | 0.0118 (15) | −0.0169 (15) |
N2 | 0.0490 (16) | 0.0552 (16) | 0.0471 (15) | −0.0011 (12) | 0.0011 (12) | −0.0184 (12) |
C1 | 0.057 (2) | 0.090 (3) | 0.071 (2) | −0.021 (2) | −0.0160 (19) | −0.014 (2) |
C2 | 0.050 (2) | 0.071 (2) | 0.068 (2) | −0.0008 (17) | −0.0046 (18) | −0.014 (2) |
C3 | 0.055 (2) | 0.0535 (19) | 0.0539 (19) | −0.0049 (15) | −0.0050 (16) | −0.0165 (15) |
C4 | 0.0471 (17) | 0.0469 (17) | 0.0386 (15) | −0.0092 (14) | 0.0009 (13) | −0.0108 (14) |
C5 | 0.063 (2) | 0.0550 (19) | 0.0518 (18) | −0.0184 (16) | 0.0030 (16) | −0.0187 (16) |
C6 | 0.075 (3) | 0.089 (3) | 0.060 (2) | −0.038 (2) | −0.0054 (19) | −0.027 (2) |
C7 | 0.0477 (18) | 0.0388 (16) | 0.0444 (16) | −0.0034 (13) | −0.0003 (14) | −0.0154 (13) |
C8 | 0.0451 (18) | 0.0404 (16) | 0.0454 (16) | −0.0001 (13) | −0.0034 (14) | −0.0143 (13) |
C9 | 0.0512 (19) | 0.0508 (18) | 0.0504 (18) | −0.0053 (14) | −0.0057 (15) | −0.0154 (15) |
C10 | 0.068 (2) | 0.0489 (18) | 0.0446 (17) | −0.0046 (15) | 0.0011 (16) | −0.0152 (14) |
C11 | 0.078 (3) | 0.055 (2) | 0.0434 (18) | −0.0033 (17) | −0.0032 (18) | −0.0175 (15) |
C12 | 0.060 (2) | 0.062 (2) | 0.0532 (19) | 0.0037 (16) | −0.0163 (17) | −0.0227 (17) |
C13 | 0.0491 (19) | 0.0452 (17) | 0.0521 (18) | 0.0017 (13) | −0.0047 (15) | −0.0176 (14) |
C14 | 0.0408 (17) | 0.0561 (19) | 0.0463 (17) | −0.0079 (14) | 0.0011 (14) | −0.0186 (16) |
C15 | 0.0414 (17) | 0.057 (2) | 0.0550 (19) | −0.0139 (14) | 0.0023 (14) | −0.0196 (17) |
C16 | 0.059 (2) | 0.071 (2) | 0.063 (2) | −0.0192 (17) | 0.0155 (17) | −0.036 (2) |
C17 | 0.075 (2) | 0.083 (3) | 0.0431 (18) | −0.031 (2) | 0.0044 (17) | −0.0192 (19) |
C18 | 0.065 (2) | 0.068 (2) | 0.051 (2) | −0.0121 (18) | −0.0023 (17) | −0.0094 (17) |
C19 | 0.057 (2) | 0.057 (2) | 0.057 (2) | −0.0036 (15) | −0.0007 (16) | −0.0186 (17) |
Br1—C10 | 1.887 (3) | C7—C8 | 1.475 (4) |
O1—C13 | 1.330 (4) | C8—C9 | 1.389 (4) |
O1—H1 | 0.8499 | C8—C13 | 1.401 (4) |
N1—C15 | 1.373 (4) | C9—C10 | 1.369 (4) |
N1—H1A | 0.8600 | C9—H9A | 0.9300 |
N1—H1B | 0.8600 | C10—C11 | 1.372 (5) |
N2—C7 | 1.281 (3) | C11—C12 | 1.361 (4) |
N2—C14 | 1.423 (3) | C11—H11A | 0.9300 |
C1—C2 | 1.356 (5) | C12—C13 | 1.391 (4) |
C1—C6 | 1.373 (6) | C12—H12A | 0.9300 |
C1—H1C | 0.9300 | C14—C19 | 1.378 (4) |
C2—C3 | 1.366 (5) | C14—C15 | 1.387 (4) |
C2—H2B | 0.9300 | C15—C16 | 1.387 (4) |
C3—C4 | 1.380 (4) | C16—C17 | 1.363 (5) |
C3—H3A | 0.9300 | C16—H16A | 0.9300 |
C4—C5 | 1.377 (4) | C17—C18 | 1.370 (5) |
C4—C7 | 1.487 (4) | C17—H17A | 0.9300 |
C5—C6 | 1.376 (5) | C18—C19 | 1.375 (4) |
C5—H5A | 0.9300 | C18—H18A | 0.9300 |
C6—H6A | 0.9300 | C19—H19A | 0.9300 |
C13—O1—H1 | 108.9 | C8—C9—H9A | 119.6 |
C15—N1—H1A | 120.0 | C9—C10—C11 | 121.2 (3) |
C15—N1—H1B | 120.0 | C9—C10—Br1 | 119.4 (3) |
H1A—N1—H1B | 120.0 | C11—C10—Br1 | 119.4 (2) |
C7—N2—C14 | 124.1 (3) | C12—C11—C10 | 119.1 (3) |
C2—C1—C6 | 119.1 (4) | C12—C11—H11A | 120.5 |
C2—C1—H1C | 120.5 | C10—C11—H11A | 120.5 |
C6—C1—H1C | 120.5 | C11—C12—C13 | 121.2 (3) |
C1—C2—C3 | 121.6 (3) | C11—C12—H12A | 119.4 |
C1—C2—H2B | 119.2 | C13—C12—H12A | 119.4 |
C3—C2—H2B | 119.2 | O1—C13—C12 | 117.7 (3) |
C2—C3—C4 | 119.8 (3) | O1—C13—C8 | 122.6 (3) |
C2—C3—H3A | 120.1 | C12—C13—C8 | 119.7 (3) |
C4—C3—H3A | 120.1 | C19—C14—C15 | 120.5 (3) |
C5—C4—C3 | 119.1 (3) | C19—C14—N2 | 122.5 (3) |
C5—C4—C7 | 120.3 (3) | C15—C14—N2 | 116.7 (3) |
C3—C4—C7 | 120.6 (3) | N1—C15—C14 | 120.8 (3) |
C6—C5—C4 | 120.1 (3) | N1—C15—C16 | 121.5 (3) |
C6—C5—H5A | 119.9 | C14—C15—C16 | 117.7 (3) |
C4—C5—H5A | 119.9 | C17—C16—C15 | 121.3 (3) |
C1—C6—C5 | 120.4 (3) | C17—C16—H16A | 119.4 |
C1—C6—H6A | 119.8 | C15—C16—H16A | 119.4 |
C5—C6—H6A | 119.8 | C16—C17—C18 | 120.9 (3) |
N2—C7—C8 | 116.4 (3) | C16—C17—H17A | 119.6 |
N2—C7—C4 | 123.2 (2) | C18—C17—H17A | 119.6 |
C8—C7—C4 | 120.3 (2) | C17—C18—C19 | 118.8 (3) |
C9—C8—C13 | 118.0 (3) | C17—C18—H18A | 120.6 |
C9—C8—C7 | 121.2 (3) | C19—C18—H18A | 120.6 |
C13—C8—C7 | 120.7 (3) | C18—C19—C14 | 120.8 (3) |
C10—C9—C8 | 120.7 (3) | C18—C19—H19A | 119.6 |
C10—C9—H9A | 119.6 | C14—C19—H19A | 119.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1i | 0.86 | 2.28 | 3.011 (3) | 142 |
O1—H1···N2 | 0.85 | 1.79 | 2.505 (3) | 141 |
N1—H1A···N2 | 0.86 | 2.41 | 2.734 (4) | 103 |
N1—H1B···Cg1ii | 0.86 | 3.20 | 3.799 (2) | 129 |
C19—H19A···Cg2iii | 0.93 | 2.98 | 3.800 (3) | 148 |
C1—H1C···Cg3iv | 0.93 | 2.76 | 3.557 (3) | 145 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C19H15BrN2O |
Mr | 367.23 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.4504 (17), 9.4206 (19), 11.141 (2) |
α, β, γ (°) | 68.94 (3), 85.40 (3), 78.31 (3) |
V (Å3) | 810.5 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.54 |
Crystal size (mm) | 0.20 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3365, 2785, 2094 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.099, 1.03 |
No. of reflections | 2785 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.28 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1i | 0.86 | 2.28 | 3.011 (3) | 142.4 |
O1—H1···N2 | 0.85 | 1.79 | 2.505 (3) | 140.6 |
N1—H1A···N2 | 0.86 | 2.41 | 2.734 (4) | 103.1 |
N1—H1B···Cg1ii | 0.86 | 3.20 | 3.799 (2) | 129 |
C19—H19A···Cg2iii | 0.93 | 2.98 | 3.800 (3) | 148 |
C1—H1C···Cg3iv | 0.93 | 2.76 | 3.557 (3) | 145 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z; (iv) x+1, y, z. |
Monocondensed Schiff bases are attractive because of their use as intermediates in the synthesis of unsymmetrical multidentate Schiff base ligands. Schiff bases also serve as potential chelating agents and possess biological activities (Yang, 2006). Transition metal complexes derived from Schiff bases are are of great interest since they exhibit numerous biological activities such as antitumor (Ranford et al., 1993), anti-candida (Majella et al., 1999), antimicrobacterial (Saha et al., 2004) and antimicrobial (Zoroddu et al., 1996) activities. In this paper, we have synthesized a new Schiff base compound by the condensation of 5-Bromo 2-hyoxybenzophenone with diaminobenzene and characterized it with X-ray crystallographic techniques.
All the bond lengths in the compounds are within normal ranges (Allen et al., 1987). The C7—N2 bond length of 1.281 (3)Å confirms it as a double bond. The C—Br bond length [1.887 (3) Å] is agreement with other reported bonds [1.884 (2)Å (Wiktor et al., 2000)].
Four atoms C4,C7,C8,N2 are in a plane (p1). The benzene ring, C8—C13, (p3), is approximately planar with its immediate substituent atoms Br1, O1, and C7, with a maximum deviation of 0.028 (1)Å for O1. The benzene ring, C14—C19, is planar with its immediate substituent atoms N1 forming the plane p4. The dihedral angles formed by p1 with the benzene ring, C1—C6, (p2), p3 and p4 are 56.5 (2), 6.2 (4) and 55.7 (1)°, respectively. The dihedral angles formed by p2 with p3 and p4 are 59.4 (2) and 61.8 (3)°. The dihedral angle between p3 and p4 is 61.8 (2)°.
The molecular structure is stabilized by intramolecular C—H···π interactions and O—H···N, N—H···O and N—H···N inter- and intra-molecular hydrogen-bond interactions [N1···Cg1 = 3.799 (2), H1B···Cg1 = 3.200 (1) Å, N1—H1B···Cg1 = 128.8 (3)° (Symmetry code: 1 - x,2 - y,-z); C1···Cg3 = 3.557 (3), H1C···Cg3 = 2.758 (2) Å, C1—H1C···Cg3 = 144.6 (2)° (Symmetry code: 1 + x,y,z); C19···Cg2 = 3.800 (3), H19A···Cg2 = 2.977 (2) Å, C19—H19A···Cg2 = 148.3 (2)° (Symmetry code: 1 - x,1 - y,-z). Cg1, Cg2 and Cg3 are the centroids of phenyl rings C1—C6, C8—C13 and C14—C19, respectively]. Hydrogen-bond interactions are list in Table 2.