organic compounds
The title compound, C27H26ClN3O3, was prepared by reacting 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one and 4-(4-chlorobenzyloxy)-3-ethoxybenzaldehyde. The central ethylvanillin group makes dihedral angles of 63.00 (11), 31.83 (7) and 74.47 (8)° with the chlorobenzene ring, the pyrazolone ring and the terminal phenyl ring, respectively. Packing is stabilized by intermolecular C—HO hydrogen bonds that form centrosymmetric dimers.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022008/bh2023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022008/bh2023Isup2.hkl |
CCDC reference: 613577
Computing details top
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
(E)-4-[4-(4-Chlorobenzyloxy)-3-ethoxybenzylideneamino]-1,5-dimethyl-2-phenyl- 1H-pyrazol-3(2H)-one top
Crystal data top
C27H26ClN3O3 | Z = 2 |
Mr = 475.96 | F(000) = 500 |
Triclinic, P1 | Dx = 1.289 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.019 (2) Å | Cell parameters from 1368 reflections |
b = 10.355 (2) Å | θ = 2.7–22.2° |
c = 12.824 (3) Å | µ = 0.19 mm−1 |
α = 77.080 (4)° | T = 294 K |
β = 83.710 (4)° | Block, yellow |
γ = 71.133 (4)° | 0.34 × 0.30 × 0.20 mm |
V = 1226.1 (4) Å3 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4299 independent reflections |
Radiation source: fine-focus sealed tube | 2253 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→11 |
Tmin = 0.928, Tmax = 0.963 | k = −7→12 |
6294 measured reflections | l = −15→14 |
Refinement top
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0704P)2 + 0.1725P] where P = (Fo2 + 2Fc2)/3 |
4299 reflections | (Δ/σ)max = 0.003 |
310 parameters | Δρmax = 0.41 e Å−3 |
18 restraints | Δρmin = −0.27 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | 1.23717 (13) | 0.40173 (14) | −0.11388 (13) | 0.1250 (6) | |
O1 | 0.6852 (2) | 0.1941 (2) | 0.0705 (2) | 0.0632 (7) | |
O2 | 0.4924 (2) | 0.3470 (3) | 0.1787 (3) | 0.0860 (9) | |
O3 | 0.1051 (2) | −0.2193 (2) | 0.39294 (18) | 0.0592 (7) | |
N1 | 0.1251 (3) | 0.0816 (3) | 0.2981 (2) | 0.0459 (7) | |
N2 | −0.2110 (3) | 0.0466 (3) | 0.3943 (2) | 0.0502 (7) | |
N3 | −0.1281 (3) | −0.0929 (3) | 0.4246 (2) | 0.0488 (7) | |
C1 | 0.9389 (4) | 0.2313 (4) | −0.1284 (3) | 0.0711 (11) | |
H1 | 0.8933 | 0.2152 | −0.1812 | 0.085* | |
C2 | 1.0408 (4) | 0.2968 (4) | −0.1579 (4) | 0.0799 (12) | |
H2 | 1.0645 | 0.3239 | −0.2298 | 0.096* | |
C3 | 1.1064 (4) | 0.3215 (4) | −0.0803 (4) | 0.0698 (11) | |
C4 | 1.0729 (4) | 0.2805 (4) | 0.0257 (3) | 0.0731 (11) | |
H4 | 1.1181 | 0.2975 | 0.0785 | 0.088* | |
C5 | 0.9722 (4) | 0.2145 (4) | 0.0532 (3) | 0.0646 (10) | |
H5 | 0.9503 | 0.1862 | 0.1253 | 0.078* | |
C6 | 0.9030 (3) | 0.1890 (3) | −0.0222 (3) | 0.0512 (9) | |
C7 | 0.7964 (3) | 0.1125 (4) | 0.0121 (3) | 0.0646 (10) | |
H7A | 0.7603 | 0.0981 | −0.0501 | 0.077* | |
H7B | 0.8397 | 0.0223 | 0.0567 | 0.077* | |
C8 | 0.5825 (3) | 0.1372 (3) | 0.1179 (3) | 0.0477 (8) | |
C9 | 0.4754 (3) | 0.2219 (3) | 0.1760 (3) | 0.0527 (9) | |
C10 | 0.3667 (3) | 0.1754 (3) | 0.2245 (3) | 0.0514 (9) | |
H10 | 0.2956 | 0.2323 | 0.2620 | 0.062* | |
C11 | 0.3596 (3) | 0.0448 (3) | 0.2193 (2) | 0.0438 (8) | |
C12 | 0.4665 (3) | −0.0376 (3) | 0.1647 (3) | 0.0488 (8) | |
H12 | 0.4650 | −0.1261 | 0.1619 | 0.059* | |
C13 | 0.5768 (3) | 0.0083 (3) | 0.1135 (3) | 0.0512 (9) | |
H13 | 0.6474 | −0.0488 | 0.0759 | 0.061* | |
C14 | 0.3819 (5) | 0.4473 (4) | 0.2154 (5) | 0.1054 (16) | |
H14A | 0.3531 | 0.4106 | 0.2877 | 0.126* | |
H14B | 0.3021 | 0.4732 | 0.1702 | 0.126* | |
C15 | 0.4249 (4) | 0.5706 (4) | 0.2146 (4) | 0.1011 (16) | |
H15A | 0.5076 | 0.5435 | 0.2557 | 0.152* | |
H15B | 0.3498 | 0.6373 | 0.2455 | 0.152* | |
H15C | 0.4454 | 0.6114 | 0.1422 | 0.152* | |
C16 | 0.2401 (3) | −0.0018 (3) | 0.2685 (2) | 0.0456 (8) | |
H16 | 0.2482 | −0.0958 | 0.2786 | 0.055* | |
C17 | 0.0127 (3) | 0.0343 (3) | 0.3443 (2) | 0.0424 (8) | |
C18 | −0.1220 (3) | 0.1215 (3) | 0.3544 (2) | 0.0450 (8) | |
C19 | −0.1730 (4) | 0.2756 (3) | 0.3275 (3) | 0.0662 (10) | |
H19A | −0.2530 | 0.3058 | 0.2832 | 0.099* | |
H19B | −0.0990 | 0.3096 | 0.2897 | 0.099* | |
H19C | −0.2000 | 0.3114 | 0.3922 | 0.099* | |
C20 | −0.3380 (3) | 0.0988 (4) | 0.4605 (3) | 0.0667 (10) | |
H20A | −0.3122 | 0.1247 | 0.5209 | 0.100* | |
H20B | −0.3822 | 0.0273 | 0.4850 | 0.100* | |
H20C | −0.4027 | 0.1787 | 0.4187 | 0.100* | |
C21 | 0.0119 (3) | −0.1061 (3) | 0.3871 (2) | 0.0444 (8) | |
C22 | −0.1927 (3) | −0.2007 (3) | 0.4409 (3) | 0.0482 (8) | |
C23 | −0.3082 (4) | −0.1838 (4) | 0.3843 (3) | 0.0633 (10) | |
H23 | −0.3457 | −0.1017 | 0.3352 | 0.076* | |
C24 | −0.3678 (4) | −0.2900 (5) | 0.4010 (4) | 0.0799 (12) | |
H24 | −0.4476 | −0.2782 | 0.3647 | 0.096* | |
C25 | −0.3105 (5) | −0.4123 (5) | 0.4705 (4) | 0.0829 (14) | |
H25 | −0.3501 | −0.4841 | 0.4801 | 0.099* | |
C26 | −0.1935 (5) | −0.4293 (4) | 0.5268 (4) | 0.0795 (13) | |
H26 | −0.1540 | −0.5129 | 0.5736 | 0.095* | |
C27 | −0.1352 (4) | −0.3214 (4) | 0.5132 (3) | 0.0636 (10) | |
H27 | −0.0587 | −0.3308 | 0.5524 | 0.076* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0838 (9) | 0.1014 (9) | 0.1851 (15) | −0.0511 (7) | 0.0359 (9) | −0.0053 (9) |
O1 | 0.0453 (13) | 0.0583 (14) | 0.0878 (19) | −0.0186 (11) | 0.0255 (13) | −0.0275 (13) |
O2 | 0.0453 (14) | 0.0658 (16) | 0.162 (3) | −0.0250 (13) | 0.0376 (16) | −0.0610 (17) |
O3 | 0.0436 (13) | 0.0482 (14) | 0.0761 (18) | −0.0111 (11) | 0.0037 (12) | −0.0004 (11) |
N1 | 0.0411 (16) | 0.0506 (16) | 0.0478 (17) | −0.0182 (13) | −0.0005 (13) | −0.0080 (13) |
N2 | 0.0400 (15) | 0.0490 (16) | 0.0583 (19) | −0.0107 (13) | 0.0056 (14) | −0.0120 (13) |
N3 | 0.0429 (16) | 0.0477 (16) | 0.0540 (18) | −0.0169 (13) | 0.0027 (13) | −0.0046 (13) |
C1 | 0.052 (2) | 0.104 (3) | 0.056 (3) | −0.020 (2) | 0.0018 (19) | −0.022 (2) |
C2 | 0.063 (3) | 0.097 (3) | 0.062 (3) | −0.020 (2) | 0.018 (2) | 0.002 (2) |
C3 | 0.047 (2) | 0.062 (2) | 0.090 (3) | −0.0184 (18) | 0.018 (2) | −0.003 (2) |
C4 | 0.060 (2) | 0.093 (3) | 0.079 (3) | −0.034 (2) | −0.001 (2) | −0.027 (2) |
C5 | 0.059 (2) | 0.086 (3) | 0.054 (2) | −0.032 (2) | 0.0109 (19) | −0.014 (2) |
C6 | 0.0346 (18) | 0.062 (2) | 0.054 (2) | −0.0116 (16) | 0.0092 (16) | −0.0162 (17) |
C7 | 0.045 (2) | 0.078 (2) | 0.075 (3) | −0.0180 (19) | 0.0151 (19) | −0.032 (2) |
C8 | 0.0361 (18) | 0.0462 (19) | 0.061 (2) | −0.0150 (15) | 0.0046 (16) | −0.0109 (16) |
C9 | 0.0416 (19) | 0.0450 (19) | 0.075 (3) | −0.0156 (16) | 0.0105 (18) | −0.0222 (17) |
C10 | 0.0399 (19) | 0.055 (2) | 0.064 (2) | −0.0173 (16) | 0.0103 (16) | −0.0235 (17) |
C11 | 0.0407 (19) | 0.0465 (19) | 0.046 (2) | −0.0156 (15) | 0.0000 (15) | −0.0101 (15) |
C12 | 0.045 (2) | 0.0462 (19) | 0.058 (2) | −0.0152 (16) | 0.0023 (17) | −0.0155 (16) |
C13 | 0.0432 (19) | 0.052 (2) | 0.057 (2) | −0.0104 (16) | 0.0070 (17) | −0.0196 (16) |
C14 | 0.079 (3) | 0.075 (3) | 0.173 (5) | −0.022 (2) | 0.007 (3) | −0.054 (3) |
C15 | 0.074 (3) | 0.068 (3) | 0.175 (5) | −0.029 (2) | 0.007 (3) | −0.048 (3) |
C16 | 0.048 (2) | 0.0465 (18) | 0.046 (2) | −0.0200 (16) | −0.0036 (16) | −0.0068 (15) |
C17 | 0.0418 (19) | 0.0486 (19) | 0.0398 (19) | −0.0192 (15) | −0.0005 (15) | −0.0080 (15) |
C18 | 0.0442 (19) | 0.0469 (19) | 0.046 (2) | −0.0168 (16) | 0.0015 (15) | −0.0122 (15) |
C19 | 0.062 (2) | 0.053 (2) | 0.081 (3) | −0.0149 (18) | 0.005 (2) | −0.0159 (19) |
C20 | 0.043 (2) | 0.084 (3) | 0.067 (3) | −0.0121 (19) | 0.0116 (18) | −0.021 (2) |
C21 | 0.0383 (19) | 0.053 (2) | 0.041 (2) | −0.0151 (16) | 0.0014 (15) | −0.0073 (15) |
C22 | 0.0414 (19) | 0.055 (2) | 0.052 (2) | −0.0221 (16) | 0.0107 (16) | −0.0141 (17) |
C23 | 0.059 (2) | 0.076 (3) | 0.063 (2) | −0.032 (2) | 0.0011 (19) | −0.0146 (19) |
C24 | 0.070 (3) | 0.091 (3) | 0.096 (4) | −0.042 (3) | 0.009 (2) | −0.034 (3) |
C25 | 0.069 (3) | 0.077 (3) | 0.125 (4) | −0.045 (3) | 0.036 (3) | −0.053 (3) |
C26 | 0.074 (3) | 0.052 (2) | 0.101 (3) | −0.022 (2) | 0.027 (3) | −0.003 (2) |
C27 | 0.050 (2) | 0.061 (2) | 0.073 (3) | −0.0179 (18) | 0.0054 (19) | −0.001 (2) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.735 (4) | C11—C16 | 1.462 (4) |
O1—C8 | 1.367 (4) | C12—C13 | 1.385 (4) |
O1—C7 | 1.416 (4) | C12—H12 | 0.9300 |
O2—C9 | 1.369 (4) | C13—H13 | 0.9300 |
O2—C14 | 1.373 (4) | C14—C15 | 1.471 (5) |
O3—C21 | 1.233 (3) | C14—H14A | 0.9700 |
N1—C16 | 1.274 (4) | C14—H14B | 0.9700 |
N1—C17 | 1.393 (4) | C15—H15A | 0.9600 |
N2—C18 | 1.352 (4) | C15—H15B | 0.9600 |
N2—N3 | 1.404 (3) | C15—H15C | 0.9600 |
N2—C20 | 1.468 (4) | C16—H16 | 0.9300 |
N3—C21 | 1.405 (4) | C17—C18 | 1.370 (4) |
N3—C22 | 1.429 (4) | C17—C21 | 1.437 (4) |
C1—C2 | 1.376 (5) | C18—C19 | 1.480 (4) |
C1—C6 | 1.379 (5) | C19—H19A | 0.9600 |
C1—H1 | 0.9300 | C19—H19B | 0.9600 |
C2—C3 | 1.361 (5) | C19—H19C | 0.9600 |
C2—H2 | 0.9300 | C20—H20A | 0.9600 |
C3—C4 | 1.369 (5) | C20—H20B | 0.9600 |
C4—C5 | 1.367 (5) | C20—H20C | 0.9600 |
C4—H4 | 0.9300 | C22—C27 | 1.374 (4) |
C5—C6 | 1.366 (5) | C22—C23 | 1.376 (4) |
C5—H5 | 0.9300 | C23—C24 | 1.379 (5) |
C6—C7 | 1.499 (5) | C23—H23 | 0.9300 |
C7—H7A | 0.9700 | C24—C25 | 1.366 (6) |
C7—H7B | 0.9700 | C24—H24 | 0.9300 |
C8—C13 | 1.368 (4) | C25—C26 | 1.385 (6) |
C8—C9 | 1.409 (4) | C25—H25 | 0.9300 |
C9—C10 | 1.364 (4) | C26—C27 | 1.390 (5) |
C10—C11 | 1.394 (4) | C26—H26 | 0.9300 |
C10—H10 | 0.9300 | C27—H27 | 0.9300 |
C11—C12 | 1.370 (4) | ||
C8—O1—C7 | 117.4 (2) | C15—C14—H14A | 109.7 |
C9—O2—C14 | 119.1 (3) | O2—C14—H14B | 109.7 |
C16—N1—C17 | 121.2 (3) | C15—C14—H14B | 109.7 |
C18—N2—N3 | 107.2 (2) | H14A—C14—H14B | 108.2 |
C18—N2—C20 | 122.7 (3) | C14—C15—H15A | 109.5 |
N3—N2—C20 | 118.2 (3) | C14—C15—H15B | 109.5 |
N2—N3—C21 | 109.0 (2) | H15A—C15—H15B | 109.5 |
N2—N3—C22 | 119.4 (2) | C14—C15—H15C | 109.5 |
C21—N3—C22 | 125.1 (3) | H15A—C15—H15C | 109.5 |
C2—C1—C6 | 121.5 (4) | H15B—C15—H15C | 109.5 |
C2—C1—H1 | 119.2 | N1—C16—C11 | 122.4 (3) |
C6—C1—H1 | 119.2 | N1—C16—H16 | 118.8 |
C3—C2—C1 | 119.1 (4) | C11—C16—H16 | 118.8 |
C3—C2—H2 | 120.5 | C18—C17—N1 | 123.1 (3) |
C1—C2—H2 | 120.5 | C18—C17—C21 | 108.1 (3) |
C2—C3—C4 | 120.6 (4) | N1—C17—C21 | 128.8 (3) |
C2—C3—Cl1 | 120.6 (4) | N2—C18—C17 | 110.2 (3) |
C4—C3—Cl1 | 118.8 (4) | N2—C18—C19 | 121.4 (3) |
C5—C4—C3 | 119.3 (4) | C17—C18—C19 | 128.4 (3) |
C5—C4—H4 | 120.4 | C18—C19—H19A | 109.5 |
C3—C4—H4 | 120.4 | C18—C19—H19B | 109.5 |
C6—C5—C4 | 121.9 (4) | H19A—C19—H19B | 109.5 |
C6—C5—H5 | 119.1 | C18—C19—H19C | 109.5 |
C4—C5—H5 | 119.1 | H19A—C19—H19C | 109.5 |
C5—C6—C1 | 117.6 (3) | H19B—C19—H19C | 109.5 |
C5—C6—C7 | 119.8 (3) | N2—C20—H20A | 109.5 |
C1—C6—C7 | 122.6 (3) | N2—C20—H20B | 109.5 |
O1—C7—C6 | 107.9 (3) | H20A—C20—H20B | 109.5 |
O1—C7—H7A | 110.1 | N2—C20—H20C | 109.5 |
C6—C7—H7A | 110.1 | H20A—C20—H20C | 109.5 |
O1—C7—H7B | 110.1 | H20B—C20—H20C | 109.5 |
C6—C7—H7B | 110.1 | O3—C21—N3 | 123.2 (3) |
H7A—C7—H7B | 108.4 | O3—C21—C17 | 132.2 (3) |
O1—C8—C13 | 125.8 (3) | N3—C21—C17 | 104.6 (3) |
O1—C8—C9 | 115.2 (3) | C27—C22—C23 | 121.3 (3) |
C13—C8—C9 | 119.0 (3) | C27—C22—N3 | 118.2 (3) |
C10—C9—O2 | 125.6 (3) | C23—C22—N3 | 120.5 (3) |
C10—C9—C8 | 119.6 (3) | C22—C23—C24 | 119.2 (4) |
O2—C9—C8 | 114.8 (3) | C22—C23—H23 | 120.4 |
C9—C10—C11 | 121.6 (3) | C24—C23—H23 | 120.4 |
C9—C10—H10 | 119.2 | C25—C24—C23 | 120.6 (4) |
C11—C10—H10 | 119.2 | C25—C24—H24 | 119.7 |
C12—C11—C10 | 118.1 (3) | C23—C24—H24 | 119.7 |
C12—C11—C16 | 120.9 (3) | C24—C25—C26 | 120.0 (4) |
C10—C11—C16 | 121.0 (3) | C24—C25—H25 | 120.0 |
C11—C12—C13 | 121.3 (3) | C26—C25—H25 | 120.0 |
C11—C12—H12 | 119.4 | C25—C26—C27 | 120.0 (4) |
C13—C12—H12 | 119.4 | C25—C26—H26 | 120.0 |
C8—C13—C12 | 120.4 (3) | C27—C26—H26 | 120.0 |
C8—C13—H13 | 119.8 | C22—C27—C26 | 118.8 (4) |
C12—C13—H13 | 119.8 | C22—C27—H27 | 120.6 |
O2—C14—C15 | 109.9 (4) | C26—C27—H27 | 120.6 |
O2—C14—H14A | 109.7 | ||
C18—N2—N3—C21 | −9.2 (3) | C9—O2—C14—C15 | 178.2 (4) |
C20—N2—N3—C21 | −153.2 (3) | C17—N1—C16—C11 | 179.7 (3) |
C18—N2—N3—C22 | −162.4 (3) | C12—C11—C16—N1 | −163.6 (3) |
C20—N2—N3—C22 | 53.6 (4) | C10—C11—C16—N1 | 15.0 (5) |
C6—C1—C2—C3 | −0.7 (6) | C16—N1—C17—C18 | −164.3 (3) |
C1—C2—C3—C4 | 0.7 (6) | C16—N1—C17—C21 | 14.7 (5) |
C1—C2—C3—Cl1 | 179.1 (3) | N3—N2—C18—C17 | 8.1 (3) |
C2—C3—C4—C5 | −0.1 (6) | C20—N2—C18—C17 | 150.0 (3) |
Cl1—C3—C4—C5 | −178.6 (3) | N3—N2—C18—C19 | −172.1 (3) |
C3—C4—C5—C6 | −0.5 (6) | C20—N2—C18—C19 | −30.2 (5) |
C4—C5—C6—C1 | 0.5 (5) | N1—C17—C18—N2 | 175.3 (3) |
C4—C5—C6—C7 | 178.2 (3) | C21—C17—C18—N2 | −3.9 (4) |
C2—C1—C6—C5 | 0.1 (5) | N1—C17—C18—C19 | −4.5 (5) |
C2—C1—C6—C7 | −177.6 (3) | C21—C17—C18—C19 | 176.3 (3) |
C8—O1—C7—C6 | −174.1 (3) | N2—N3—C21—O3 | −172.8 (3) |
C5—C6—C7—O1 | 62.8 (4) | C22—N3—C21—O3 | −21.5 (5) |
C1—C6—C7—O1 | −119.6 (3) | N2—N3—C21—C17 | 6.7 (3) |
C7—O1—C8—C13 | −0.4 (5) | C22—N3—C21—C17 | 158.0 (3) |
C7—O1—C8—C9 | 179.2 (3) | C18—C17—C21—O3 | 177.6 (3) |
C14—O2—C9—C10 | −12.7 (6) | N1—C17—C21—O3 | −1.6 (6) |
C14—O2—C9—C8 | 167.8 (4) | C18—C17—C21—N3 | −1.8 (3) |
O1—C8—C9—C10 | 178.8 (3) | N1—C17—C21—N3 | 179.0 (3) |
C13—C8—C9—C10 | −1.5 (5) | N2—N3—C22—C27 | −150.8 (3) |
O1—C8—C9—O2 | −1.7 (4) | C21—N3—C22—C27 | 60.6 (4) |
C13—C8—C9—O2 | 178.0 (3) | N2—N3—C22—C23 | 30.1 (4) |
O2—C9—C10—C11 | −178.6 (3) | C21—N3—C22—C23 | −118.5 (3) |
C8—C9—C10—C11 | 0.9 (5) | C27—C22—C23—C24 | 0.4 (5) |
C9—C10—C11—C12 | 0.8 (5) | N3—C22—C23—C24 | 179.5 (3) |
C9—C10—C11—C16 | −177.9 (3) | C22—C23—C24—C25 | −2.0 (6) |
C10—C11—C12—C13 | −1.7 (5) | C23—C24—C25—C26 | 1.5 (6) |
C16—C11—C12—C13 | 176.9 (3) | C24—C25—C26—C27 | 0.6 (6) |
O1—C8—C13—C12 | −179.7 (3) | C23—C22—C27—C26 | 1.7 (5) |
C9—C8—C13—C12 | 0.6 (5) | N3—C22—C27—C26 | −177.5 (3) |
C11—C12—C13—C8 | 1.1 (5) | C25—C26—C27—C22 | −2.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H26···O3i | 0.93 | 2.60 | 3.395 (4) | 144 |
Symmetry code: (i) −x, −y−1, −z+1. |