| Literature DB >> 22058766 |
Hatem A Abdel-Aziz, Khalid A Al-Rashood, Seik Weng Ng, Edward R T Tiekink.
Abstract
The title compound, C(25)H(22)N(2)O(4)S, features a tetra-substituted pyrazole ring. The dihedral angles formed between the five-membered ring (r.m.s. deviation = 0.007 Å) and the N- and C-bound phenyl rings are 48.10 (7) and 72.01 (7) °, respectively, indicating that the planes through the residues are significantly twisted from the plane through the heterocycle. The ester-CO(2) group is also twisted out of this plane, with an O-C-C-N torsion angle of -29.04 (11)°. The sulfonyl-O atoms lie to one side of the pyrazole plane and the sulfonyl-phenyl ring to the other. The dihedral angle between the two ring planes is 70.63 (7) °. Supra-molecular arrays are formed in the crystal structure sustained by C-H⋯O and C-H⋯π(pyrazole) inter-actions and methyl-C-H⋯π(N-bound benzene) contacts.Entities:
Year: 2011 PMID: 22058766 PMCID: PMC3201465 DOI: 10.1107/S1600536811036580
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C25H22N2O4S | |
| Triclinic, | |
| Hall symbol: -P 1 | Cu |
| Cell parameters from 5331 reflections | |
| θ = 3.2–74.1° | |
| µ = 1.60 mm−1 | |
| α = 68.818 (4)° | |
| β = 87.773 (3)° | Block, yellow |
| γ = 81.241 (4)° | 0.40 × 0.30 × 0.20 mm |
| Agilent SuperNova Dual diffractometer with Atlas detector | 4304 independent reflections |
| Radiation source: SuperNova (Cu) X-ray Source | 4106 reflections with |
| mirror | |
| Detector resolution: 10.4041 pixels mm-1 | θmax = 74.3°, θmin = 3.2° |
| ω scan | |
| Absorption correction: multi-scan ( | |
| 7378 measured reflections |
| Refinement on | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| Hydrogen site location: inferred from neighbouring sites | |
| H-atom parameters constrained | |
| 4304 reflections | (Δ/σ)max < 0.001 |
| 290 parameters | Δρmax = 0.35 e Å−3 |
| 0 restraints | Δρmin = −0.42 e Å−3 |
| 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 |
| S1 | 0.44173 (4) | 0.70984 (3) | 0.10567 (2) | 0.01551 (10) | |
| O1 | 0.24561 (13) | 0.75817 (9) | 0.09106 (7) | 0.0201 (2) | |
| O2 | 0.54033 (14) | 0.66162 (9) | 0.03658 (7) | 0.0202 (2) | |
| O3 | 0.08177 (14) | 0.59487 (10) | 0.38398 (9) | 0.0275 (2) | |
| O4 | 0.19467 (16) | 0.77438 (10) | 0.28475 (8) | 0.0280 (2) | |
| N1 | 0.40421 (15) | 0.44865 (11) | 0.36938 (8) | 0.0161 (2) | |
| N2 | 0.55383 (15) | 0.39169 (10) | 0.33340 (8) | 0.0150 (2) | |
| C1 | −0.2495 (2) | 0.66923 (19) | 0.37793 (12) | 0.0333 (4) | |
| H1A | −0.3481 | 0.7238 | 0.3990 | 0.050* | |
| H1B | −0.2743 | 0.5785 | 0.4023 | 0.050* | |
| H1C | −0.2470 | 0.7016 | 0.3071 | 0.050* | |
| C2 | −0.0656 (2) | 0.67488 (16) | 0.41664 (13) | 0.0286 (3) | |
| H2A | −0.0413 | 0.7666 | 0.3935 | 0.034* | |
| H2B | −0.0672 | 0.6418 | 0.4882 | 0.034* | |
| C3 | 0.20136 (18) | 0.65804 (13) | 0.31954 (9) | 0.0171 (3) | |
| C4 | 0.35304 (18) | 0.56389 (12) | 0.30001 (9) | 0.0156 (3) | |
| C5 | 0.46821 (18) | 0.58099 (12) | 0.21819 (9) | 0.0152 (3) | |
| C6 | 0.59874 (18) | 0.46782 (12) | 0.24248 (9) | 0.0148 (3) | |
| C7 | 0.55863 (19) | 0.83215 (12) | 0.11696 (9) | 0.0171 (3) | |
| C8 | 0.7518 (2) | 0.82100 (14) | 0.10621 (10) | 0.0225 (3) | |
| H8 | 0.8189 | 0.7490 | 0.0927 | 0.027* | |
| C9 | 0.8443 (2) | 0.91673 (15) | 0.11553 (12) | 0.0272 (3) | |
| H9 | 0.9760 | 0.9106 | 0.1086 | 0.033* | |
| C10 | 0.7444 (2) | 1.02163 (14) | 0.13504 (11) | 0.0271 (3) | |
| H10 | 0.8083 | 1.0868 | 0.1417 | 0.033* | |
| C11 | 0.5522 (2) | 1.03192 (14) | 0.14486 (11) | 0.0247 (3) | |
| H11 | 0.4851 | 1.1045 | 0.1577 | 0.030* | |
| C12 | 0.4571 (2) | 0.93691 (13) | 0.13606 (10) | 0.0206 (3) | |
| H12 | 0.3254 | 0.9434 | 0.1429 | 0.025* | |
| C13 | 0.76709 (18) | 0.42800 (12) | 0.19410 (9) | 0.0149 (3) | |
| C14 | 0.94252 (19) | 0.42706 (13) | 0.23053 (10) | 0.0182 (3) | |
| H14 | 0.9520 | 0.4530 | 0.2845 | 0.022* | |
| C15 | 1.10313 (19) | 0.38814 (13) | 0.18770 (10) | 0.0207 (3) | |
| H15 | 1.2224 | 0.3885 | 0.2120 | 0.025* | |
| C16 | 1.0902 (2) | 0.34872 (13) | 0.10965 (10) | 0.0209 (3) | |
| H16 | 1.2004 | 0.3216 | 0.0808 | 0.025* | |
| C17 | 0.9159 (2) | 0.34899 (13) | 0.07374 (10) | 0.0204 (3) | |
| H17 | 0.9071 | 0.3216 | 0.0205 | 0.025* | |
| C18 | 0.75398 (19) | 0.38910 (13) | 0.11527 (9) | 0.0179 (3) | |
| H18 | 0.6350 | 0.3900 | 0.0901 | 0.022* | |
| C19 | 0.63396 (17) | 0.26085 (12) | 0.39171 (9) | 0.0155 (3) | |
| C20 | 0.66215 (19) | 0.16297 (13) | 0.35283 (10) | 0.0184 (3) | |
| H20 | 0.6400 | 0.1831 | 0.2859 | 0.022* | |
| C21 | 0.72330 (19) | 0.03502 (13) | 0.41333 (10) | 0.0203 (3) | |
| H21 | 0.7447 | −0.0321 | 0.3869 | 0.024* | |
| C22 | 0.75393 (19) | 0.00307 (13) | 0.51205 (10) | 0.0185 (3) | |
| C23 | 0.72672 (19) | 0.10390 (13) | 0.54866 (10) | 0.0188 (3) | |
| H23 | 0.7490 | 0.0843 | 0.6155 | 0.023* | |
| C24 | 0.66765 (18) | 0.23258 (13) | 0.48902 (10) | 0.0173 (3) | |
| H24 | 0.6506 | 0.3005 | 0.5148 | 0.021* | |
| C25 | 0.8151 (2) | −0.13619 (13) | 0.57784 (11) | 0.0236 (3) | |
| H25A | 0.7437 | −0.1943 | 0.5618 | 0.035* | |
| H25B | 0.7929 | −0.1440 | 0.6452 | 0.035* | |
| H25C | 0.9485 | −0.1610 | 0.5694 | 0.035* |
| S1 | 0.01730 (17) | 0.01487 (16) | 0.01383 (16) | −0.00005 (12) | −0.00058 (11) | −0.00538 (12) |
| O1 | 0.0178 (5) | 0.0213 (5) | 0.0204 (5) | 0.0010 (4) | −0.0032 (4) | −0.0078 (4) |
| O2 | 0.0245 (5) | 0.0202 (5) | 0.0160 (5) | 0.0000 (4) | 0.0020 (4) | −0.0081 (4) |
| O3 | 0.0186 (5) | 0.0235 (5) | 0.0454 (7) | −0.0040 (4) | 0.0133 (4) | −0.0193 (5) |
| O4 | 0.0408 (6) | 0.0168 (5) | 0.0235 (5) | 0.0020 (4) | 0.0076 (4) | −0.0071 (4) |
| N1 | 0.0138 (5) | 0.0168 (5) | 0.0186 (5) | −0.0007 (4) | 0.0022 (4) | −0.0082 (4) |
| N2 | 0.0137 (5) | 0.0147 (5) | 0.0161 (5) | 0.0000 (4) | 0.0019 (4) | −0.0059 (4) |
| C1 | 0.0208 (8) | 0.0498 (10) | 0.0336 (9) | 0.0035 (7) | 0.0001 (6) | −0.0237 (8) |
| C2 | 0.0190 (7) | 0.0290 (8) | 0.0450 (9) | −0.0018 (6) | 0.0104 (6) | −0.0237 (7) |
| C3 | 0.0162 (6) | 0.0197 (6) | 0.0172 (6) | −0.0001 (5) | −0.0026 (5) | −0.0096 (5) |
| C4 | 0.0145 (6) | 0.0162 (6) | 0.0174 (6) | −0.0017 (5) | −0.0006 (5) | −0.0079 (5) |
| C5 | 0.0158 (6) | 0.0146 (6) | 0.0159 (6) | −0.0019 (5) | −0.0003 (5) | −0.0065 (5) |
| C6 | 0.0153 (6) | 0.0156 (6) | 0.0151 (6) | −0.0035 (5) | −0.0003 (5) | −0.0068 (5) |
| C7 | 0.0204 (7) | 0.0145 (6) | 0.0143 (6) | −0.0021 (5) | −0.0003 (5) | −0.0029 (5) |
| C8 | 0.0215 (7) | 0.0195 (7) | 0.0240 (7) | −0.0006 (5) | 0.0022 (5) | −0.0062 (6) |
| C9 | 0.0211 (7) | 0.0243 (7) | 0.0330 (8) | −0.0051 (6) | 0.0006 (6) | −0.0059 (6) |
| C10 | 0.0314 (8) | 0.0199 (7) | 0.0294 (8) | −0.0087 (6) | −0.0025 (6) | −0.0059 (6) |
| C11 | 0.0310 (8) | 0.0150 (6) | 0.0271 (7) | −0.0011 (6) | −0.0006 (6) | −0.0072 (6) |
| C12 | 0.0212 (7) | 0.0172 (6) | 0.0208 (7) | 0.0002 (5) | −0.0005 (5) | −0.0050 (5) |
| C13 | 0.0164 (6) | 0.0118 (6) | 0.0152 (6) | −0.0012 (5) | 0.0020 (5) | −0.0037 (5) |
| C14 | 0.0192 (7) | 0.0178 (6) | 0.0193 (6) | −0.0036 (5) | 0.0011 (5) | −0.0083 (5) |
| C15 | 0.0160 (7) | 0.0202 (7) | 0.0249 (7) | −0.0030 (5) | 0.0014 (5) | −0.0070 (5) |
| C16 | 0.0209 (7) | 0.0169 (6) | 0.0223 (7) | −0.0007 (5) | 0.0075 (5) | −0.0055 (5) |
| C17 | 0.0264 (7) | 0.0179 (6) | 0.0171 (6) | −0.0013 (5) | 0.0033 (5) | −0.0075 (5) |
| C18 | 0.0195 (7) | 0.0173 (6) | 0.0173 (6) | −0.0020 (5) | −0.0006 (5) | −0.0068 (5) |
| C19 | 0.0122 (6) | 0.0137 (6) | 0.0188 (6) | −0.0014 (5) | 0.0018 (5) | −0.0040 (5) |
| C20 | 0.0184 (7) | 0.0191 (6) | 0.0183 (6) | −0.0026 (5) | 0.0015 (5) | −0.0077 (5) |
| C21 | 0.0200 (7) | 0.0167 (6) | 0.0258 (7) | −0.0025 (5) | 0.0037 (5) | −0.0099 (5) |
| C22 | 0.0134 (6) | 0.0166 (6) | 0.0233 (7) | −0.0025 (5) | 0.0029 (5) | −0.0046 (5) |
| C23 | 0.0169 (6) | 0.0199 (7) | 0.0177 (6) | −0.0028 (5) | 0.0013 (5) | −0.0046 (5) |
| C24 | 0.0165 (6) | 0.0168 (6) | 0.0192 (6) | −0.0022 (5) | 0.0020 (5) | −0.0073 (5) |
| C25 | 0.0216 (7) | 0.0168 (7) | 0.0278 (7) | −0.0017 (5) | 0.0031 (6) | −0.0033 (6) |
| S1—O1 | 1.4354 (10) | C11—C12 | 1.388 (2) |
| S1—O2 | 1.4378 (10) | C11—H11 | 0.9500 |
| S1—C5 | 1.7544 (13) | C12—H12 | 0.9500 |
| S1—C7 | 1.7624 (14) | C13—C18 | 1.3947 (18) |
| O3—C3 | 1.3380 (17) | C13—C14 | 1.3971 (19) |
| O3—C2 | 1.4635 (16) | C14—C15 | 1.3894 (19) |
| O4—C3 | 1.1968 (17) | C14—H14 | 0.9500 |
| N1—C4 | 1.3274 (17) | C15—C16 | 1.387 (2) |
| N1—N2 | 1.3592 (15) | C15—H15 | 0.9500 |
| N2—C6 | 1.3646 (17) | C16—C17 | 1.389 (2) |
| N2—C19 | 1.4362 (16) | C16—H16 | 0.9500 |
| C1—C2 | 1.489 (2) | C17—C18 | 1.3909 (19) |
| C1—H1A | 0.9800 | C17—H17 | 0.9500 |
| C1—H1B | 0.9800 | C18—H18 | 0.9500 |
| C1—H1C | 0.9800 | C19—C24 | 1.3843 (19) |
| C2—H2A | 0.9900 | C19—C20 | 1.3875 (18) |
| C2—H2B | 0.9900 | C20—C21 | 1.3897 (19) |
| C3—C4 | 1.4913 (17) | C20—H20 | 0.9500 |
| C4—C5 | 1.4165 (18) | C21—C22 | 1.394 (2) |
| C5—C6 | 1.3911 (18) | C21—H21 | 0.9500 |
| C6—C13 | 1.4809 (17) | C22—C23 | 1.3942 (19) |
| C7—C12 | 1.3891 (19) | C22—C25 | 1.5054 (18) |
| C7—C8 | 1.394 (2) | C23—C24 | 1.3893 (19) |
| C8—C9 | 1.387 (2) | C23—H23 | 0.9500 |
| C8—H8 | 0.9500 | C24—H24 | 0.9500 |
| C9—C10 | 1.389 (2) | C25—H25A | 0.9800 |
| C9—H9 | 0.9500 | C25—H25B | 0.9800 |
| C10—C11 | 1.386 (2) | C25—H25C | 0.9800 |
| C10—H10 | 0.9500 | ||
| O1—S1—O2 | 119.33 (6) | C12—C11—H11 | 119.8 |
| O1—S1—C5 | 106.92 (6) | C10—C11—H11 | 119.8 |
| O2—S1—C5 | 106.93 (6) | C11—C12—C7 | 118.58 (13) |
| O1—S1—C7 | 109.11 (6) | C11—C12—H12 | 120.7 |
| O2—S1—C7 | 107.81 (6) | C7—C12—H12 | 120.7 |
| C5—S1—C7 | 105.98 (6) | C18—C13—C14 | 119.85 (12) |
| C3—O3—C2 | 117.09 (11) | C18—C13—C6 | 121.66 (12) |
| C4—N1—N2 | 104.77 (10) | C14—C13—C6 | 118.48 (11) |
| N1—N2—C6 | 113.13 (10) | C15—C14—C13 | 119.85 (12) |
| N1—N2—C19 | 117.27 (10) | C15—C14—H14 | 120.1 |
| C6—N2—C19 | 129.49 (11) | C13—C14—H14 | 120.1 |
| C2—C1—H1A | 109.5 | C16—C15—C14 | 120.34 (13) |
| C2—C1—H1B | 109.5 | C16—C15—H15 | 119.8 |
| H1A—C1—H1B | 109.5 | C14—C15—H15 | 119.8 |
| C2—C1—H1C | 109.5 | C15—C16—C17 | 119.82 (12) |
| H1A—C1—H1C | 109.5 | C15—C16—H16 | 120.1 |
| H1B—C1—H1C | 109.5 | C17—C16—H16 | 120.1 |
| O3—C2—C1 | 109.39 (12) | C16—C17—C18 | 120.42 (13) |
| O3—C2—H2A | 109.8 | C16—C17—H17 | 119.8 |
| C1—C2—H2A | 109.8 | C18—C17—H17 | 119.8 |
| O3—C2—H2B | 109.8 | C17—C18—C13 | 119.72 (13) |
| C1—C2—H2B | 109.8 | C17—C18—H18 | 120.1 |
| H2A—C2—H2B | 108.2 | C13—C18—H18 | 120.1 |
| O4—C3—O3 | 125.36 (12) | C24—C19—C20 | 120.89 (12) |
| O4—C3—C4 | 123.58 (13) | C24—C19—N2 | 118.50 (11) |
| O3—C3—C4 | 110.98 (11) | C20—C19—N2 | 120.40 (12) |
| N1—C4—C5 | 111.39 (11) | C21—C20—C19 | 119.00 (12) |
| N1—C4—C3 | 118.83 (11) | C21—C20—H20 | 120.5 |
| C5—C4—C3 | 129.57 (12) | C19—C20—H20 | 120.5 |
| C6—C5—C4 | 105.42 (11) | C20—C21—C22 | 121.40 (13) |
| C6—C5—S1 | 126.52 (10) | C20—C21—H21 | 119.3 |
| C4—C5—S1 | 127.84 (10) | C22—C21—H21 | 119.3 |
| N2—C6—C5 | 105.29 (11) | C23—C22—C21 | 118.19 (12) |
| N2—C6—C13 | 121.29 (11) | C23—C22—C25 | 120.56 (13) |
| C5—C6—C13 | 133.20 (12) | C21—C22—C25 | 121.25 (13) |
| C12—C7—C8 | 121.65 (13) | C24—C23—C22 | 121.16 (13) |
| C12—C7—S1 | 119.59 (11) | C24—C23—H23 | 119.4 |
| C8—C7—S1 | 118.76 (10) | C22—C23—H23 | 119.4 |
| C9—C8—C7 | 118.91 (13) | C19—C24—C23 | 119.33 (12) |
| C9—C8—H8 | 120.5 | C19—C24—H24 | 120.3 |
| C7—C8—H8 | 120.5 | C23—C24—H24 | 120.3 |
| C10—C9—C8 | 119.93 (14) | C22—C25—H25A | 109.5 |
| C10—C9—H9 | 120.0 | C22—C25—H25B | 109.5 |
| C8—C9—H9 | 120.0 | H25A—C25—H25B | 109.5 |
| C9—C10—C11 | 120.51 (14) | C22—C25—H25C | 109.5 |
| C9—C10—H10 | 119.7 | H25A—C25—H25C | 109.5 |
| C11—C10—H10 | 119.7 | H25B—C25—H25C | 109.5 |
| C12—C11—C10 | 120.40 (13) | ||
| C4—N1—N2—C6 | −0.25 (14) | C12—C7—C8—C9 | 0.4 (2) |
| C4—N1—N2—C19 | −176.77 (11) | S1—C7—C8—C9 | −179.68 (11) |
| C3—O3—C2—C1 | 110.72 (15) | C7—C8—C9—C10 | −0.2 (2) |
| C2—O3—C3—O4 | −2.0 (2) | C8—C9—C10—C11 | −0.3 (2) |
| C2—O3—C3—C4 | 174.84 (12) | C9—C10—C11—C12 | 0.5 (2) |
| N2—N1—C4—C5 | 0.83 (14) | C10—C11—C12—C7 | −0.2 (2) |
| N2—N1—C4—C3 | −174.42 (11) | C8—C7—C12—C11 | −0.3 (2) |
| O4—C3—C4—N1 | 147.76 (14) | S1—C7—C12—C11 | 179.87 (11) |
| O3—C3—C4—N1 | −29.15 (17) | N2—C6—C13—C18 | 109.94 (15) |
| O4—C3—C4—C5 | −26.5 (2) | C5—C6—C13—C18 | −76.46 (19) |
| O3—C3—C4—C5 | 156.60 (13) | N2—C6—C13—C14 | −68.59 (16) |
| N1—C4—C5—C6 | −1.11 (15) | C5—C6—C13—C14 | 105.00 (17) |
| C3—C4—C5—C6 | 173.49 (13) | C18—C13—C14—C15 | 0.40 (19) |
| N1—C4—C5—S1 | 173.74 (10) | C6—C13—C14—C15 | 178.96 (12) |
| C3—C4—C5—S1 | −11.7 (2) | C13—C14—C15—C16 | −0.8 (2) |
| O1—S1—C5—C6 | 145.06 (11) | C14—C15—C16—C17 | 0.4 (2) |
| O2—S1—C5—C6 | 16.17 (13) | C15—C16—C17—C18 | 0.3 (2) |
| C7—S1—C5—C6 | −98.65 (12) | C16—C17—C18—C13 | −0.6 (2) |
| O1—S1—C5—C4 | −28.76 (13) | C14—C13—C18—C17 | 0.31 (19) |
| O2—S1—C5—C4 | −157.65 (12) | C6—C13—C18—C17 | −178.21 (12) |
| C7—S1—C5—C4 | 87.53 (13) | N1—N2—C19—C24 | −46.78 (16) |
| N1—N2—C6—C5 | −0.43 (14) | C6—N2—C19—C24 | 137.37 (14) |
| C19—N2—C6—C5 | 175.56 (12) | N1—N2—C19—C20 | 127.96 (13) |
| N1—N2—C6—C13 | 174.73 (11) | C6—N2—C19—C20 | −47.90 (19) |
| C19—N2—C6—C13 | −9.3 (2) | C24—C19—C20—C21 | 0.6 (2) |
| C4—C5—C6—N2 | 0.88 (14) | N2—C19—C20—C21 | −173.97 (12) |
| S1—C5—C6—N2 | −174.06 (10) | C19—C20—C21—C22 | 1.0 (2) |
| C4—C5—C6—C13 | −173.44 (13) | C20—C21—C22—C23 | −1.8 (2) |
| S1—C5—C6—C13 | 11.6 (2) | C20—C21—C22—C25 | 178.30 (13) |
| O1—S1—C7—C12 | 16.54 (13) | C21—C22—C23—C24 | 1.1 (2) |
| O2—S1—C7—C12 | 147.52 (11) | C25—C22—C23—C24 | −179.04 (12) |
| C5—S1—C7—C12 | −98.27 (11) | C20—C19—C24—C23 | −1.4 (2) |
| O1—S1—C7—C8 | −163.34 (10) | N2—C19—C24—C23 | 173.35 (11) |
| O2—S1—C7—C8 | −32.36 (12) | C22—C23—C24—C19 | 0.5 (2) |
| C5—S1—C7—C8 | 81.85 (12) |
| Cg1 and Cg2 are the centroids of the N1,N2,C4–C6 and C19–C24 rings, respectively. |
| H··· | ||||
| C9—H9···O1i | 0.95 | 2.45 | 3.2392 (19) | 140 |
| C16—H16···O2ii | 0.95 | 2.49 | 3.3928 (18) | 158 |
| C17—H17···O1iii | 0.95 | 2.50 | 3.3895 (18) | 157 |
| C18—H18···O2iii | 0.95 | 2.58 | 3.4031 (17) | 145 |
| C23—H23···O4iv | 0.95 | 2.59 | 3.3155 (18) | 133 |
| C15—H15···Cg1i | 0.95 | 2.80 | 3.6781 (15) | 154 |
| C25—H25c···Cg2v | 0.98 | 2.64 | 3.5649 (16) | 157 |
Hydrogen-bond geometry (Å, °)
Cg1 and Cg2 are the centroids of the N1,N2,C4–C6 and C19–C24 rings, respectively.
| H⋯ | ||||
|---|---|---|---|---|
| C9—H9⋯O1i | 0.95 | 2.45 | 3.2392 (19) | 140 |
| C16—H16⋯O2ii | 0.95 | 2.49 | 3.3928 (18) | 158 |
| C17—H17⋯O1iii | 0.95 | 2.50 | 3.3895 (18) | 157 |
| C18—H18⋯O2iii | 0.95 | 2.58 | 3.4031 (17) | 145 |
| C23—H23⋯O4iv | 0.95 | 2.59 | 3.3155 (18) | 133 |
| C15—H15⋯ | 0.95 | 2.80 | 3.6781 (15) | 154 |
| C25—H25c⋯ | 0.98 | 2.64 | 3.5649 (16) | 157 |
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .