



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015023452/su5255sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015023452/su5255Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015023452/su5255Isup3.cml |
CCDC reference: 1440831
Phthalazine derivatives have been reported to act as anticonvulsants (Carling et al. 2004), potential inhibitors of serotonin reuptake (Cashman & Ghirmai, 2009), anti-proliferative agents against different human and murine tumor cells (Hall et al., 1992, 2001) and vasorelaxant agents (Nomoto et al. 1990). Therefore, a number of synthetic methods have been developed in recent years to uncover a variety of new reagents for the synthesis of phthalazine derivatives (Mosaddegh & Hassankhani, 2011; Hasaninejed et al., 2012; Keshipour et al., 2012). In previous work, we have reported the synthesis and structure heterocyclic compounds bearing a phthalazine unit (Bouraiou et al., 2015). Herein, we describe the synthesis and crystal structure of the title indazolo phthalazine-trione derivative, resulting from the reaction of phthalhydrazide, cyclohexa-1,3-dione and benzaldehyde in the presence of catalytic amounts of sulfuric acid.
The title compound, Fig. 1, consists of an indazolone moiety, bearing a phenyl group, fused to a phthalazine ring system [r.m.s. deviation = 0.018 Å]. The phenyl ring (C16—C21) is almost normal to the mean plane of the five-membered ring (N1/N2/C9/C10/C15) of the indazolone moiety with a dihedral angle of 89.64 (7)°. The six-membered ring of the indazolone moiety (C10—C15) has an envelope conformation with the central methylene C atom, C13, as the flap.
In the crystal, molecules are linked via C—H···O hydrogen bonds forming slabs parallel to the bc plane (Table 1 and Fig. 2). The slabs are linked via C—H···π (Table 1) and slipped parallel π-π interactions [the shortest inter-centroid distance involves Cg2···Cg3i = 3.6430 (8) Å; Cg2 and Cg3 are the centroids of rings (N1/N2/C1/C2/C7/C8) and (C2—C7), respectively; inter-planar distance = 3.457 (5); slippage = 1.07 Å; symmetry code: (i) -x+1, -y, -z], forming a three-dimensional structure.
The title compound was synthesized in accordance with established methods (Khurana & Magoo, 2009; Bouraiou et al., 2015). Spectroscopic results and physical properties are in agreement with literature reports (Nagarapu et al., 2009). The solid obtained, was recrystallized in a hot CHCl3/EtOAc/EtOH (1:1:1) mixture giving yellow crystals of the title compound. MS (ES-API): m/z [M+H]+ = 345.1; 1H-NMR δ (ppm) (250 MHz, CDCl3): 8.35–8.23 (m, 2H), 7.88–7.84 (m, 2H), 7.32–7.30 (m, 5H), 6.46 (s, 1H), 3.63–3.30 (m, 2H), 2.51–2.46 (m, 2H), 2.32–2.22 (m, 2H); 13C-NMR δ (ppm) (62.9 MHz, 3): 192.6, 156.1, 154.3, 152.3, 136.4, 134.6, 133.6, 129.1, 129.0, 128.7, 128.0, 127.8, 127.2, 119.7, 65.0, 37.0, 24.6, 22.3.
Phthalazine derivatives have been reported to act as anticonvulsants (Carling et al. 2004), potential inhibitors of serotonin reuptake (Cashman & Ghirmai, 2009), anti-proliferative agents against different human and murine tumor cells (Hall et al., 1992, 2001) and vasorelaxant agents (Nomoto et al. 1990). Therefore, a number of synthetic methods have been developed in recent years to uncover a variety of new reagents for the synthesis of phthalazine derivatives (Mosaddegh & Hassankhani, 2011; Hasaninejed et al., 2012; Keshipour et al., 2012). In previous work, we have reported the synthesis and structure heterocyclic compounds bearing a phthalazine unit (Bouraiou et al., 2015). Herein, we describe the synthesis and crystal structure of the title indazolo phthalazine-trione derivative, resulting from the reaction of phthalhydrazide, cyclohexa-1,3-dione and benzaldehyde in the presence of catalytic amounts of sulfuric acid.
The title compound, Fig. 1, consists of an indazolone moiety, bearing a phenyl group, fused to a phthalazine ring system [r.m.s. deviation = 0.018 Å]. The phenyl ring (C16—C21) is almost normal to the mean plane of the five-membered ring (N1/N2/C9/C10/C15) of the indazolone moiety with a dihedral angle of 89.64 (7)°. The six-membered ring of the indazolone moiety (C10—C15) has an envelope conformation with the central methylene C atom, C13, as the flap.
In the crystal, molecules are linked via C—H···O hydrogen bonds forming slabs parallel to the bc plane (Table 1 and Fig. 2). The slabs are linked via C—H···π (Table 1) and slipped parallel π-π interactions [the shortest inter-centroid distance involves Cg2···Cg3i = 3.6430 (8) Å; Cg2 and Cg3 are the centroids of rings (N1/N2/C1/C2/C7/C8) and (C2—C7), respectively; inter-planar distance = 3.457 (5); slippage = 1.07 Å; symmetry code: (i) -x+1, -y, -z], forming a three-dimensional structure.
For application of phthalazine derivatives see: Mosaddegh & Hassankhani (2011); Hasaninejed et al. (2012); Keshipour et al. (2012). For the synthesis of this class of compounds, see: Carling et al. (2004); Cashman & Ghirmai (2009); Hall et al. (1992, 2001); Bouraiou et al. (2015); Nomoto et al. (1990). For the synthesis of the title compound, see: Bouraiou et al. (2015); Khurana & Magoo (2009); Nagarapu et al. (2009).
The title compound was synthesized in accordance with established methods (Khurana & Magoo, 2009; Bouraiou et al., 2015). Spectroscopic results and physical properties are in agreement with literature reports (Nagarapu et al., 2009). The solid obtained, was recrystallized in a hot CHCl3/EtOAc/EtOH (1:1:1) mixture giving yellow crystals of the title compound. MS (ES-API): m/z [M+H]+ = 345.1; 1H-NMR δ (ppm) (250 MHz, CDCl3): 8.35–8.23 (m, 2H), 7.88–7.84 (m, 2H), 7.32–7.30 (m, 5H), 6.46 (s, 1H), 3.63–3.30 (m, 2H), 2.51–2.46 (m, 2H), 2.32–2.22 (m, 2H); 13C-NMR δ (ppm) (62.9 MHz, 3): 192.6, 156.1, 154.3, 152.3, 136.4, 134.6, 133.6, 129.1, 129.0, 128.7, 128.0, 127.8, 127.2, 119.7, 65.0, 37.0, 24.6, 22.3.
Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were located in difference Fourier maps but introduced in calculated positions and refined as riding atoms: C—H = 0.93-0.98 Å with Uiso(H) = 1.2 Ueq(C).
Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
C21H16N2O3 | F(000) = 720 |
Mr = 344.36 | Dx = 1.362 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4002 reflections |
a = 8.9028 (2) Å | θ = 3.0–30.5° |
b = 11.4507 (3) Å | µ = 0.09 mm−1 |
c = 17.0274 (4) Å | T = 295 K |
β = 104.618 (1)° | Prism, yellow |
V = 1679.64 (7) Å3 | 0.13 × 0.09 × 0.05 mm |
Z = 4 |
Bruker APEXII diffractometer | 4873 independent reflections |
Radiation source: Enraf Nonius FR590 | 3617 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0 |
CCD rotation images, thick slices scans | θmax = 30.6°, θmin = 3.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2011) | h = −12→12 |
Tmin = 0.957, Tmax = 0.986 | k = 0→16 |
4873 measured reflections | l = 0→23 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.1115P)2 + 0.0058P] where P = (Fo2 + 2Fc2)/3 |
4873 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.6 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C21H16N2O3 | V = 1679.64 (7) Å3 |
Mr = 344.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.9028 (2) Å | µ = 0.09 mm−1 |
b = 11.4507 (3) Å | T = 295 K |
c = 17.0274 (4) Å | 0.13 × 0.09 × 0.05 mm |
β = 104.618 (1)° |
Bruker APEXII diffractometer | 4873 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2011) | 3617 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.986 | Rint = 0 |
4873 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.6 e Å−3 |
4873 reflections | Δρmin = −0.28 e Å−3 |
235 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
C1 | 0.75069 (15) | 0.02395 (11) | 0.00764 (7) | 0.0373 (3) | |
C2 | 0.68676 (14) | −0.05024 (11) | 0.06179 (7) | 0.0350 (3) | |
C3 | 0.69309 (16) | −0.17117 (12) | 0.05347 (9) | 0.0452 (3) | |
H3 | 0.7353 | −0.2031 | 0.0136 | 0.054* | |
C4 | 0.63708 (18) | −0.24340 (13) | 0.10405 (10) | 0.0519 (4) | |
H4 | 0.6422 | −0.324 | 0.0986 | 0.062* | |
C5 | 0.57284 (17) | −0.19596 (15) | 0.16328 (10) | 0.0525 (4) | |
H5 | 0.5359 | −0.245 | 0.1977 | 0.063* | |
C6 | 0.56360 (16) | −0.07659 (14) | 0.17128 (9) | 0.0455 (3) | |
H6 | 0.5189 | −0.0454 | 0.2105 | 0.055* | |
C7 | 0.62114 (13) | −0.00234 (12) | 0.12069 (7) | 0.0359 (3) | |
C8 | 0.60888 (14) | 0.12553 (12) | 0.12975 (7) | 0.0369 (3) | |
C9 | 0.66558 (13) | 0.31891 (11) | 0.07410 (7) | 0.0332 (3) | |
H9 | 0.5574 | 0.3454 | 0.0611 | 0.04* | |
C10 | 0.73305 (14) | 0.33728 (11) | 0.00262 (7) | 0.0350 (3) | |
C11 | 0.74291 (16) | 0.44774 (12) | −0.03792 (8) | 0.0425 (3) | |
C12 | 0.8090 (2) | 0.43883 (17) | −0.11124 (11) | 0.0664 (5) | |
H12A | 0.7242 | 0.4281 | −0.1592 | 0.08* | |
H12B | 0.8599 | 0.5119 | −0.1175 | 0.08* | |
C13 | 0.9230 (3) | 0.34114 (17) | −0.10670 (12) | 0.0689 (5) | |
H13A | 1.0152 | 0.358 | −0.0639 | 0.083* | |
H13B | 0.9534 | 0.3375 | −0.1575 | 0.083* | |
C14 | 0.85967 (17) | 0.22277 (14) | −0.09042 (8) | 0.0464 (3) | |
H14A | 0.7873 | 0.1942 | −0.1392 | 0.056* | |
H14B | 0.9439 | 0.167 | −0.0747 | 0.056* | |
C15 | 0.77933 (14) | 0.23569 (11) | −0.02380 (7) | 0.0347 (3) | |
C16 | 0.75871 (13) | 0.37878 (11) | 0.15078 (7) | 0.0329 (3) | |
C17 | 0.91360 (15) | 0.35115 (14) | 0.18289 (8) | 0.0455 (3) | |
H17 | 0.9599 | 0.2926 | 0.1593 | 0.055* | |
C18 | 1.00001 (17) | 0.41101 (16) | 0.25044 (8) | 0.0532 (4) | |
H18 | 1.1036 | 0.3916 | 0.2723 | 0.064* | |
C19 | 0.93283 (19) | 0.49868 (14) | 0.28486 (8) | 0.0504 (4) | |
H19 | 0.9917 | 0.5398 | 0.3291 | 0.06* | |
C20 | 0.7781 (2) | 0.52582 (13) | 0.25386 (8) | 0.0510 (4) | |
H20 | 0.7319 | 0.5841 | 0.2778 | 0.061* | |
C21 | 0.69169 (16) | 0.46548 (12) | 0.18660 (8) | 0.0414 (3) | |
H21 | 0.5875 | 0.4839 | 0.1656 | 0.05* | |
N1 | 0.74174 (12) | 0.14291 (9) | 0.02082 (6) | 0.0351 (2) | |
N2 | 0.67235 (12) | 0.19043 (10) | 0.07981 (6) | 0.0355 (2) | |
O1 | 0.80699 (15) | −0.01280 (10) | −0.04590 (6) | 0.0574 (3) | |
O2 | 0.54814 (13) | 0.17285 (10) | 0.17821 (6) | 0.0539 (3) | |
O3 | 0.69339 (14) | 0.53847 (10) | −0.01668 (7) | 0.0591 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0465 (6) | 0.0302 (6) | 0.0353 (6) | 0.0009 (5) | 0.0105 (5) | 0.0003 (5) |
C2 | 0.0378 (6) | 0.0291 (6) | 0.0350 (6) | −0.0002 (5) | 0.0031 (4) | 0.0034 (4) |
C3 | 0.0509 (7) | 0.0333 (7) | 0.0476 (7) | 0.0004 (6) | 0.0055 (6) | 0.0010 (5) |
C4 | 0.0562 (8) | 0.0319 (7) | 0.0630 (9) | −0.0035 (6) | 0.0064 (7) | 0.0072 (6) |
C5 | 0.0506 (7) | 0.0452 (8) | 0.0599 (9) | −0.0093 (7) | 0.0109 (6) | 0.0166 (7) |
C6 | 0.0442 (7) | 0.0452 (8) | 0.0483 (7) | −0.0045 (6) | 0.0139 (5) | 0.0077 (6) |
C7 | 0.0345 (6) | 0.0353 (7) | 0.0359 (6) | −0.0030 (5) | 0.0049 (4) | 0.0035 (5) |
C8 | 0.0389 (6) | 0.0371 (7) | 0.0362 (6) | −0.0031 (5) | 0.0120 (4) | 0.0007 (5) |
C9 | 0.0361 (5) | 0.0289 (6) | 0.0347 (6) | 0.0007 (5) | 0.0093 (4) | −0.0005 (4) |
C10 | 0.0397 (6) | 0.0333 (7) | 0.0314 (5) | −0.0019 (5) | 0.0079 (4) | 0.0008 (4) |
C11 | 0.0483 (7) | 0.0347 (7) | 0.0437 (7) | −0.0015 (6) | 0.0103 (5) | 0.0054 (5) |
C12 | 0.0946 (13) | 0.0509 (10) | 0.0660 (10) | 0.0039 (9) | 0.0433 (9) | 0.0181 (8) |
C13 | 0.0916 (13) | 0.0537 (11) | 0.0784 (11) | −0.0096 (9) | 0.0530 (10) | 0.0009 (9) |
C14 | 0.0575 (8) | 0.0435 (8) | 0.0449 (7) | −0.0030 (7) | 0.0254 (6) | −0.0026 (6) |
C15 | 0.0395 (6) | 0.0325 (6) | 0.0325 (6) | −0.0035 (5) | 0.0097 (4) | −0.0003 (5) |
C16 | 0.0388 (6) | 0.0304 (6) | 0.0307 (5) | −0.0023 (5) | 0.0110 (4) | 0.0020 (4) |
C17 | 0.0405 (6) | 0.0532 (9) | 0.0426 (6) | 0.0032 (6) | 0.0101 (5) | −0.0055 (6) |
C18 | 0.0423 (7) | 0.0717 (12) | 0.0419 (7) | −0.0076 (7) | 0.0037 (5) | 0.0002 (7) |
C19 | 0.0636 (9) | 0.0497 (8) | 0.0348 (6) | −0.0164 (7) | 0.0068 (6) | −0.0031 (6) |
C20 | 0.0734 (10) | 0.0380 (7) | 0.0417 (7) | 0.0005 (7) | 0.0145 (6) | −0.0052 (6) |
C21 | 0.0491 (7) | 0.0354 (7) | 0.0399 (6) | 0.0057 (6) | 0.0115 (5) | 0.0002 (5) |
N1 | 0.0445 (5) | 0.0300 (5) | 0.0341 (5) | −0.0001 (4) | 0.0159 (4) | −0.0015 (4) |
N2 | 0.0449 (5) | 0.0295 (5) | 0.0362 (5) | −0.0021 (4) | 0.0178 (4) | −0.0020 (4) |
O1 | 0.0895 (8) | 0.0395 (6) | 0.0544 (6) | 0.0026 (6) | 0.0389 (6) | −0.0047 (5) |
O2 | 0.0670 (7) | 0.0471 (7) | 0.0603 (6) | −0.0031 (5) | 0.0394 (5) | −0.0030 (5) |
O3 | 0.0773 (8) | 0.0356 (6) | 0.0685 (7) | 0.0087 (5) | 0.0262 (6) | 0.0081 (5) |
C1—O1 | 1.2206 (16) | C11—C12 | 1.512 (2) |
C1—N1 | 1.3861 (16) | C12—C13 | 1.499 (3) |
C1—C2 | 1.4700 (18) | C12—H12A | 0.97 |
C2—C7 | 1.3942 (19) | C12—H12B | 0.97 |
C2—C3 | 1.3945 (19) | C13—C14 | 1.520 (2) |
C3—C4 | 1.375 (2) | C13—H13A | 0.97 |
C3—H3 | 0.93 | C13—H13B | 0.97 |
C4—C5 | 1.389 (3) | C14—C15 | 1.4932 (19) |
C4—H4 | 0.93 | C14—H14A | 0.97 |
C5—C6 | 1.378 (2) | C14—H14B | 0.97 |
C5—H5 | 0.93 | C15—N1 | 1.3951 (16) |
C6—C7 | 1.3964 (18) | C16—C21 | 1.3775 (18) |
C6—H6 | 0.93 | C16—C17 | 1.3857 (18) |
C7—C8 | 1.4793 (19) | C17—C18 | 1.3921 (19) |
C8—O2 | 1.2215 (16) | C17—H17 | 0.93 |
C8—N2 | 1.3554 (16) | C18—C19 | 1.373 (2) |
C9—N2 | 1.4746 (17) | C18—H18 | 0.93 |
C9—C10 | 1.5019 (17) | C19—C20 | 1.381 (2) |
C9—C16 | 1.5217 (16) | C19—H19 | 0.93 |
C9—H9 | 0.98 | C20—C21 | 1.3915 (19) |
C10—C15 | 1.3487 (18) | C20—H20 | 0.93 |
C10—C11 | 1.4541 (18) | C21—H21 | 0.93 |
C11—O3 | 1.2187 (18) | N1—N2 | 1.4142 (14) |
O1—C1—N1 | 120.73 (12) | H12A—C12—H12B | 107.6 |
O1—C1—C2 | 124.48 (13) | C12—C13—C14 | 113.43 (16) |
N1—C1—C2 | 114.78 (11) | C12—C13—H13A | 108.9 |
C7—C2—C3 | 119.92 (13) | C14—C13—H13A | 108.9 |
C7—C2—C1 | 121.51 (12) | C12—C13—H13B | 108.9 |
C3—C2—C1 | 118.57 (13) | C14—C13—H13B | 108.9 |
C4—C3—C2 | 120.21 (15) | H13A—C13—H13B | 107.7 |
C4—C3—H3 | 119.9 | C15—C14—C13 | 108.72 (12) |
C2—C3—H3 | 119.9 | C15—C14—H14A | 109.9 |
C3—C4—C5 | 120.01 (15) | C13—C14—H14A | 109.9 |
C3—C4—H4 | 120 | C15—C14—H14B | 109.9 |
C5—C4—H4 | 120 | C13—C14—H14B | 109.9 |
C6—C5—C4 | 120.36 (14) | H14A—C14—H14B | 108.3 |
C6—C5—H5 | 119.8 | C10—C15—N1 | 109.86 (11) |
C4—C5—H5 | 119.8 | C10—C15—C14 | 125.73 (12) |
C5—C6—C7 | 120.17 (15) | N1—C15—C14 | 124.41 (12) |
C5—C6—H6 | 119.9 | C21—C16—C17 | 119.28 (12) |
C7—C6—H6 | 119.9 | C21—C16—C9 | 120.10 (11) |
C2—C7—C6 | 119.32 (13) | C17—C16—C9 | 120.54 (11) |
C2—C7—C8 | 121.32 (11) | C16—C17—C18 | 120.07 (14) |
C6—C7—C8 | 119.35 (12) | C16—C17—H17 | 120 |
O2—C8—N2 | 120.42 (13) | C18—C17—H17 | 120 |
O2—C8—C7 | 124.50 (12) | C19—C18—C17 | 120.21 (13) |
N2—C8—C7 | 115.08 (11) | C19—C18—H18 | 119.9 |
N2—C9—C10 | 100.09 (10) | C17—C18—H18 | 119.9 |
N2—C9—C16 | 112.86 (9) | C18—C19—C20 | 120.09 (13) |
C10—C9—C16 | 112.92 (10) | C18—C19—H19 | 120 |
N2—C9—H9 | 110.2 | C20—C19—H19 | 120 |
C10—C9—H9 | 110.2 | C19—C20—C21 | 119.60 (14) |
C16—C9—H9 | 110.2 | C19—C20—H20 | 120.2 |
C15—C10—C11 | 122.13 (12) | C21—C20—H20 | 120.2 |
C15—C10—C9 | 111.58 (11) | C16—C21—C20 | 120.74 (13) |
C11—C10—C9 | 126.22 (12) | C16—C21—H21 | 119.6 |
O3—C11—C10 | 122.07 (13) | C20—C21—H21 | 119.6 |
O3—C11—C12 | 123.22 (13) | C1—N1—C15 | 128.95 (11) |
C10—C11—C12 | 114.58 (13) | C1—N1—N2 | 123.12 (11) |
C13—C12—C11 | 114.02 (14) | C15—N1—N2 | 107.56 (10) |
C13—C12—H12A | 108.7 | C8—N2—N1 | 124.10 (11) |
C11—C12—H12A | 108.7 | C8—N2—C9 | 124.87 (11) |
C13—C12—H12B | 108.7 | N1—N2—C9 | 110.79 (9) |
C11—C12—H12B | 108.7 |
Cg3 is the centroid of the C2–C7 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2i | 0.93 | 2.59 | 3.488 (2) | 163 |
C9—H9···O3ii | 0.98 | 2.54 | 3.501 (2) | 165 |
C18—H18···Cg3iii | 0.93 | 2.68 | 3.552 (2) | 156 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) −x+2, y+1/2, −z+1/2. |
Cg3 is the centroid of the C2–C7 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2i | 0.93 | 2.59 | 3.488 (2) | 163 |
C9—H9···O3ii | 0.98 | 2.54 | 3.501 (2) | 165 |
C18—H18···Cg3iii | 0.93 | 2.68 | 3.552 (2) | 156 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) −x+2, y+1/2, −z+1/2. |