organic compounds
4-{[5-Methyl-2-(propan-2-yl)phenoxy]methyl}-1-(4-nitrobenzyl)-1H-1,2,3-triazole
aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Imouzzer, BP 2202, Fez, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: azzeddinesahbi1982@gmail.com
The 20H22N4O3, comprises two independent molecules (A and B) with markedly different conformations as the C—H bonds of the imidazole rings point in opposite directions. In the crystal, C—H⋯N hydrogen bonds form chains of molecules extending along the b-axis direction, while C—H⋯O hydrogen bonds form zigzag chains along a. Additional intermolecular N O⋯π(ring) contacts form parallel chains of like molecules along a. The structure was refined as a two-component twin.
of the title compound, CKeywords: crystal structure; hydrogen bond; triazole.
CCDC reference: 1542021
Structure description
1,2,3-Triazole derivatives are often recognized as precursors in the synthesis of a variety of therapeutic agents. Indeed, et al., 1995), and are known to be antineoplastic (Passannanti et al.,1998), antimicrobial (Sheremet et al., 2004) and anti-HIV agents (Velázquez et al., 1998). In this work we have synthesized 4-{[5-Methyl-2-(propan-2-yl)phenoxy]methyl}-1-(4-nitrobenzyl)-1H-1,2,3-triazole by a 1,3-dipolar cycloaddition reaction of 4-nitrobenzoyl azide with 1-isopropyl-4-methyl-2-(prop-2-yn-1-yloxy)benzene and report its structure here.
containing this motif exhibit anticancer activity (StéphanThe A and B, with markedly different conformations (Fig. 1). The difference between the two unique molecules lies in the fact that the triazole ring is rotated by approximately 180° about the C7—N2 or C27—N6 bonds so that the C8—H8 and C28—H28 bonds point in diametrically opposite directions, as shown by the N2—C7—C4—C5 and N6—C27—C24—C25 torsion angles of 88.4 (3) and −89.4 (3)° respectively. Interestingly other features of the two molecules are quite similar, with the dihedral angles between the N2 and N6 imidazole rings and the corresponding nitrophenyl rings being 68.94 (9) and 67.37 (9)°, respectively, while those between the same imidazole rings and the C11–C16 and C21–C26 benzene rings are 65.85 (9) and 65.21 (9)°, respectively.
of the title compound comprises two independent molecules,The two unique molecules are linked by a weak C8—H8⋯N8 hydrogen bond and these pairs of molecules are further linked along the b-axis direction by C28—H28⋯N4i hydrogen bonds (Table 1 and Fig. 2). A combination of C5—H5⋯O4ii and C25—H25⋯O1iii hydrogen bonds link alternate A and B molecules into zigzag chains along a (Table 1, Fig. 3). Additionally, the crystal packing is supplemented by N1 O1⋯π(ring)v [O1⋯centroid of N2–N4/C8/C9 = 3.540 (2) Å; symmetry code: (v) −1 + x, y, z]. These link type A molecules into chains along the a-axis direction. A second and parallel set of chains of B molecules form in an obverse fashion through N5 O4⋯π(ring)vi [O4⋯centroid of N6–N8/C28/C29 = 3.550 (2) Å; symmetry code: (vi) 1 + x, y, z] interactions (Fig. 4).
Synthesis and crystallization
In a vial fitted with a screw cap, nitrobenzyl azide (100 mg, 0.56 mmol) and 1-isopropyl-4-methyl-2-(prop-2-yn-1-yloxy)benzene (110 mg, 0.58 mmol) were added to a mixture of copper(II) sulfate pentahydrate (7 mg, 0.028 mmol), sodium ascorbate (16.6 mg, 0.083 mmol), and β-cyclodextrin (15.9 mg, 0.014 mmol) dissolved in H2O (1 ml) at room temperature. The reaction mixture was stirred for 15 min at room temperature. The resulting mixture was poured into CH2Cl2 (3 ml) and H2O (3 ml), and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (3 ml) three times. The product was obtained as colorless crystals in a yield of 90%.
Refinement
Crystal data, data collection and structure . The structure was refined as a two-component twin.
details are summarized in Table 2Structural data
CCDC reference: 1542021
https://doi.org/10.1107/S2414314617005168/sj4099sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005168/sj4099Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617005168/sj4099Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617005168/sj4099Isup4.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016) and CELL_NOW (Sheldrick, 2008); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C20H22N4O3 | Z = 4 |
Mr = 366.41 | F(000) = 776 |
Triclinic, P1 | Dx = 1.297 Mg m−3 |
a = 9.4118 (3) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 10.8934 (4) Å | Cell parameters from 9905 reflections |
c = 18.6996 (7) Å | θ = 4.1–72.5° |
α = 101.629 (1)° | µ = 0.73 mm−1 |
β = 91.752 (1)° | T = 150 K |
γ = 90.351 (1)° | Column, colourless |
V = 1876.83 (12) Å3 | 0.22 × 0.13 × 0.11 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 11537 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 9810 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.033 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.4°, θmin = 4.1° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009) | k = −13→13 |
Tmin = 0.81, Tmax = 0.92 | l = 0→23 |
22212 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.197 | w = 1/[σ2(Fo2) + (0.1284P)2 + 0.5216P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
11537 reflections | Δρmax = 0.34 e Å−3 |
495 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0089 (12) |
Experimental. Analysis of 2112 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the triclinic system and to be twinned by a 180° rotation about the c* axis. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW. |
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. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.0186 (2) | 0.6403 (2) | 0.05682 (12) | 0.0451 (5) | |
O2 | −0.0124 (2) | 0.48631 (19) | 0.11339 (12) | 0.0416 (5) | |
O3 | 1.01236 (18) | 0.83073 (17) | 0.33021 (9) | 0.0279 (4) | |
N1 | 0.0461 (2) | 0.5660 (2) | 0.08658 (12) | 0.0289 (5) | |
N2 | 0.71275 (19) | 0.67371 (17) | 0.15685 (11) | 0.0212 (4) | |
N3 | 0.7185 (2) | 0.79683 (19) | 0.15655 (12) | 0.0295 (5) | |
N4 | 0.7727 (2) | 0.85253 (19) | 0.22071 (12) | 0.0290 (5) | |
C1 | 0.2027 (2) | 0.5720 (2) | 0.08933 (12) | 0.0220 (5) | |
C2 | 0.2757 (3) | 0.4906 (2) | 0.12426 (14) | 0.0266 (5) | |
H2 | 0.2266 | 0.4331 | 0.1470 | 0.032* | |
C3 | 0.4234 (3) | 0.4952 (2) | 0.12530 (13) | 0.0264 (5) | |
H3 | 0.4764 | 0.4401 | 0.1489 | 0.032* | |
C4 | 0.4939 (2) | 0.5800 (2) | 0.09194 (12) | 0.0205 (5) | |
C5 | 0.4171 (2) | 0.6616 (2) | 0.05791 (13) | 0.0257 (5) | |
H5 | 0.4657 | 0.7203 | 0.0358 | 0.031* | |
C6 | 0.2695 (3) | 0.6577 (2) | 0.05611 (13) | 0.0262 (5) | |
H6 | 0.2159 | 0.7127 | 0.0326 | 0.031* | |
C7 | 0.6549 (2) | 0.5839 (2) | 0.09328 (13) | 0.0254 (5) | |
H7A | 0.6916 | 0.4994 | 0.0946 | 0.030* | |
H7B | 0.6874 | 0.6078 | 0.0480 | 0.030* | |
C8 | 0.7630 (2) | 0.6501 (2) | 0.22044 (12) | 0.0214 (5) | |
H8 | 0.7698 | 0.5711 | 0.2344 | 0.026* | |
C9 | 0.8023 (2) | 0.7649 (2) | 0.26084 (13) | 0.0216 (5) | |
C10 | 0.8668 (2) | 0.7957 (2) | 0.33600 (13) | 0.0253 (5) | |
H10A | 0.8155 | 0.8658 | 0.3661 | 0.030* | |
H10B | 0.8611 | 0.7221 | 0.3594 | 0.030* | |
C11 | 1.0938 (2) | 0.8565 (2) | 0.39394 (13) | 0.0231 (5) | |
C12 | 1.2326 (2) | 0.8995 (2) | 0.38645 (13) | 0.0239 (5) | |
C13 | 1.3178 (3) | 0.9287 (2) | 0.44992 (14) | 0.0283 (5) | |
H13 | 1.4118 | 0.9591 | 0.4470 | 0.034* | |
C14 | 1.2696 (3) | 0.9145 (2) | 0.51735 (14) | 0.0295 (5) | |
H14 | 1.3311 | 0.9352 | 0.5594 | 0.035* | |
C15 | 1.1329 (3) | 0.8707 (2) | 0.52406 (13) | 0.0267 (5) | |
C16 | 1.0454 (3) | 0.8421 (2) | 0.46120 (14) | 0.0266 (5) | |
H16 | 0.9513 | 0.8123 | 0.4645 | 0.032* | |
C17 | 1.2829 (3) | 0.9113 (2) | 0.31143 (13) | 0.0268 (5) | |
H17 | 1.2032 | 0.9476 | 0.2861 | 0.032* | |
C18 | 1.4120 (3) | 0.9978 (3) | 0.31445 (17) | 0.0409 (7) | |
H18A | 1.4950 | 0.9597 | 0.3337 | 0.061* | |
H18B | 1.3932 | 1.0787 | 0.3464 | 0.061* | |
H18C | 1.4306 | 1.0107 | 0.2652 | 0.061* | |
C19 | 1.3141 (3) | 0.7820 (3) | 0.26560 (14) | 0.0363 (6) | |
H19A | 1.2280 | 0.7294 | 0.2604 | 0.055* | |
H19B | 1.3900 | 0.7427 | 0.2898 | 0.055* | |
H19C | 1.3442 | 0.7909 | 0.2172 | 0.055* | |
C20 | 1.0772 (3) | 0.8530 (3) | 0.59602 (15) | 0.0331 (6) | |
H20A | 1.0893 | 0.7655 | 0.6005 | 0.050* | |
H20B | 0.9760 | 0.8738 | 0.5983 | 0.050* | |
H20C | 1.1299 | 0.9081 | 0.6361 | 0.050* | |
O4 | 1.4652 (2) | 0.1501 (2) | 0.05767 (14) | 0.0534 (6) | |
O5 | 1.4666 (2) | −0.0108 (2) | 0.10798 (14) | 0.0483 (6) | |
O6 | 0.46802 (17) | 0.33027 (16) | 0.33204 (9) | 0.0274 (4) | |
N5 | 1.4050 (2) | 0.0711 (2) | 0.08389 (12) | 0.0318 (5) | |
N6 | 0.7479 (2) | 0.17490 (18) | 0.15999 (11) | 0.0220 (4) | |
N7 | 0.7423 (2) | 0.29755 (19) | 0.15935 (12) | 0.0289 (5) | |
N8 | 0.6953 (2) | 0.35348 (19) | 0.22316 (12) | 0.0295 (5) | |
C21 | 1.2489 (2) | 0.0760 (2) | 0.08802 (13) | 0.0233 (5) | |
C22 | 1.1811 (3) | −0.0049 (2) | 0.12393 (14) | 0.0269 (5) | |
H22 | 1.2336 | −0.0622 | 0.1461 | 0.032* | |
C23 | 1.0336 (3) | −0.0007 (2) | 0.12694 (14) | 0.0267 (5) | |
H23 | 0.9845 | −0.0556 | 0.1515 | 0.032* | |
C24 | 0.9577 (2) | 0.0835 (2) | 0.09428 (12) | 0.0217 (5) | |
C25 | 1.0299 (2) | 0.1645 (2) | 0.05917 (13) | 0.0251 (5) | |
H25 | 0.9779 | 0.2226 | 0.0374 | 0.030* | |
C26 | 1.1767 (3) | 0.1619 (2) | 0.05538 (14) | 0.0271 (5) | |
H26 | 1.2262 | 0.2172 | 0.0312 | 0.032* | |
C27 | 0.7972 (2) | 0.0858 (2) | 0.09618 (13) | 0.0256 (5) | |
H27A | 0.7584 | 0.1094 | 0.0511 | 0.031* | |
H27B | 0.7608 | 0.0008 | 0.0975 | 0.031* | |
C28 | 0.7040 (2) | 0.1506 (2) | 0.22331 (13) | 0.0221 (5) | |
H28 | 0.6978 | 0.0715 | 0.2371 | 0.027* | |
C29 | 0.6701 (2) | 0.2653 (2) | 0.26358 (13) | 0.0223 (5) | |
C30 | 0.6138 (2) | 0.2968 (2) | 0.33840 (13) | 0.0249 (5) | |
H30A | 0.6218 | 0.2237 | 0.3623 | 0.030* | |
H30B | 0.6687 | 0.3676 | 0.3684 | 0.030* | |
C31 | 0.3940 (2) | 0.3557 (2) | 0.39575 (13) | 0.0238 (5) | |
C32 | 0.2544 (3) | 0.3990 (2) | 0.38793 (13) | 0.0250 (5) | |
C33 | 0.1778 (3) | 0.4283 (2) | 0.45124 (14) | 0.0286 (5) | |
H33 | 0.0840 | 0.4591 | 0.4483 | 0.034* | |
C34 | 0.2336 (3) | 0.4141 (2) | 0.51889 (14) | 0.0296 (5) | |
H34 | 0.1775 | 0.4350 | 0.5609 | 0.036* | |
C35 | 0.3703 (3) | 0.3697 (2) | 0.52572 (13) | 0.0271 (5) | |
C36 | 0.4499 (3) | 0.3416 (2) | 0.46302 (14) | 0.0270 (5) | |
H36 | 0.5442 | 0.3122 | 0.4665 | 0.032* | |
C37 | 0.1960 (3) | 0.4112 (2) | 0.31303 (13) | 0.0272 (5) | |
H37 | 0.2734 | 0.4478 | 0.2881 | 0.033* | |
C38 | 0.1579 (3) | 0.2821 (3) | 0.26654 (14) | 0.0359 (6) | |
H38A | 0.1249 | 0.2915 | 0.2177 | 0.054* | |
H38B | 0.0823 | 0.2433 | 0.2897 | 0.054* | |
H38C | 0.2420 | 0.2289 | 0.2624 | 0.054* | |
C39 | 0.0688 (3) | 0.4979 (3) | 0.31605 (16) | 0.0397 (7) | |
H39A | 0.0937 | 0.5795 | 0.3469 | 0.060* | |
H39B | −0.0118 | 0.4610 | 0.3365 | 0.060* | |
H39C | 0.0428 | 0.5090 | 0.2666 | 0.060* | |
C40 | 0.4336 (3) | 0.3527 (3) | 0.59797 (14) | 0.0337 (6) | |
H40A | 0.4188 | 0.2658 | 0.6032 | 0.051* | |
H40B | 0.3875 | 0.4094 | 0.6377 | 0.051* | |
H40C | 0.5357 | 0.3718 | 0.6001 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0218 (9) | 0.0650 (14) | 0.0571 (13) | 0.0067 (9) | −0.0009 (9) | 0.0332 (11) |
O2 | 0.0242 (9) | 0.0456 (12) | 0.0578 (13) | −0.0069 (8) | 0.0084 (9) | 0.0164 (10) |
O3 | 0.0226 (8) | 0.0359 (9) | 0.0249 (9) | −0.0091 (7) | −0.0044 (7) | 0.0069 (7) |
N1 | 0.0197 (10) | 0.0365 (12) | 0.0301 (11) | −0.0008 (8) | 0.0016 (8) | 0.0058 (9) |
N2 | 0.0165 (8) | 0.0209 (9) | 0.0264 (10) | −0.0024 (7) | −0.0017 (7) | 0.0059 (7) |
N3 | 0.0297 (11) | 0.0221 (10) | 0.0380 (12) | −0.0030 (8) | −0.0087 (9) | 0.0108 (9) |
N4 | 0.0301 (11) | 0.0202 (10) | 0.0362 (12) | −0.0030 (8) | −0.0091 (9) | 0.0060 (8) |
C1 | 0.0170 (10) | 0.0266 (11) | 0.0208 (11) | −0.0014 (8) | 0.0005 (8) | 0.0012 (9) |
C2 | 0.0257 (12) | 0.0275 (12) | 0.0282 (12) | −0.0033 (9) | 0.0024 (9) | 0.0098 (10) |
C3 | 0.0238 (11) | 0.0288 (12) | 0.0286 (12) | 0.0006 (9) | −0.0024 (9) | 0.0114 (10) |
C4 | 0.0162 (10) | 0.0232 (11) | 0.0202 (11) | −0.0010 (8) | −0.0014 (8) | 0.0001 (8) |
C5 | 0.0221 (11) | 0.0280 (12) | 0.0283 (12) | −0.0036 (9) | −0.0003 (9) | 0.0090 (10) |
C6 | 0.0222 (11) | 0.0288 (12) | 0.0296 (12) | 0.0018 (9) | −0.0009 (9) | 0.0108 (10) |
C7 | 0.0167 (11) | 0.0319 (12) | 0.0253 (12) | −0.0010 (9) | −0.0012 (8) | 0.0010 (9) |
C8 | 0.0201 (10) | 0.0199 (11) | 0.0253 (11) | −0.0014 (8) | −0.0018 (8) | 0.0076 (9) |
C9 | 0.0179 (10) | 0.0188 (10) | 0.0282 (12) | −0.0023 (8) | −0.0021 (9) | 0.0053 (9) |
C10 | 0.0197 (11) | 0.0277 (12) | 0.0281 (12) | −0.0067 (9) | −0.0028 (9) | 0.0052 (9) |
C11 | 0.0223 (11) | 0.0223 (11) | 0.0238 (12) | −0.0020 (9) | −0.0047 (9) | 0.0034 (9) |
C12 | 0.0230 (11) | 0.0224 (11) | 0.0257 (12) | −0.0020 (9) | −0.0023 (9) | 0.0038 (9) |
C13 | 0.0214 (11) | 0.0312 (13) | 0.0313 (13) | −0.0033 (9) | −0.0042 (9) | 0.0045 (10) |
C14 | 0.0283 (12) | 0.0309 (13) | 0.0279 (13) | −0.0016 (10) | −0.0063 (10) | 0.0041 (10) |
C15 | 0.0301 (12) | 0.0245 (12) | 0.0254 (12) | 0.0016 (10) | −0.0006 (10) | 0.0046 (9) |
C16 | 0.0249 (12) | 0.0246 (12) | 0.0301 (13) | −0.0025 (9) | −0.0005 (9) | 0.0050 (10) |
C17 | 0.0269 (12) | 0.0293 (12) | 0.0238 (12) | −0.0050 (10) | −0.0026 (9) | 0.0048 (9) |
C18 | 0.0355 (14) | 0.0487 (17) | 0.0402 (16) | −0.0145 (13) | 0.0024 (12) | 0.0128 (13) |
C19 | 0.0460 (16) | 0.0378 (15) | 0.0233 (13) | −0.0014 (12) | 0.0020 (11) | 0.0016 (11) |
C20 | 0.0355 (14) | 0.0377 (14) | 0.0277 (13) | −0.0008 (11) | 0.0004 (10) | 0.0107 (11) |
O4 | 0.0243 (10) | 0.0775 (17) | 0.0696 (15) | −0.0073 (10) | 0.0044 (10) | 0.0417 (13) |
O5 | 0.0241 (9) | 0.0473 (12) | 0.0762 (16) | 0.0072 (9) | −0.0005 (10) | 0.0187 (11) |
O6 | 0.0229 (8) | 0.0355 (9) | 0.0243 (9) | 0.0086 (7) | 0.0066 (7) | 0.0064 (7) |
N5 | 0.0211 (10) | 0.0402 (12) | 0.0333 (12) | −0.0020 (9) | 0.0024 (8) | 0.0052 (10) |
N6 | 0.0188 (9) | 0.0215 (9) | 0.0261 (10) | 0.0024 (7) | 0.0057 (7) | 0.0053 (8) |
N7 | 0.0312 (11) | 0.0226 (10) | 0.0357 (12) | 0.0042 (8) | 0.0106 (9) | 0.0106 (8) |
N8 | 0.0330 (11) | 0.0214 (10) | 0.0357 (12) | 0.0032 (8) | 0.0120 (9) | 0.0078 (8) |
C21 | 0.0168 (11) | 0.0270 (12) | 0.0245 (11) | −0.0002 (9) | 0.0020 (8) | 0.0014 (9) |
C22 | 0.0254 (12) | 0.0258 (12) | 0.0310 (13) | 0.0032 (9) | 0.0019 (9) | 0.0091 (10) |
C23 | 0.0237 (11) | 0.0288 (12) | 0.0297 (12) | −0.0015 (9) | 0.0043 (9) | 0.0100 (10) |
C24 | 0.0204 (11) | 0.0220 (11) | 0.0213 (11) | 0.0014 (8) | 0.0035 (8) | 0.0006 (8) |
C25 | 0.0219 (11) | 0.0261 (12) | 0.0282 (12) | 0.0022 (9) | 0.0012 (9) | 0.0072 (9) |
C26 | 0.0247 (12) | 0.0285 (12) | 0.0294 (12) | −0.0030 (9) | 0.0030 (9) | 0.0089 (10) |
C27 | 0.0176 (11) | 0.0299 (12) | 0.0264 (12) | 0.0013 (9) | 0.0027 (9) | −0.0013 (9) |
C28 | 0.0217 (11) | 0.0189 (11) | 0.0270 (12) | 0.0010 (8) | 0.0033 (9) | 0.0072 (9) |
C29 | 0.0188 (10) | 0.0207 (11) | 0.0284 (12) | 0.0006 (8) | 0.0040 (9) | 0.0067 (9) |
C30 | 0.0219 (11) | 0.0251 (12) | 0.0277 (12) | 0.0054 (9) | 0.0045 (9) | 0.0046 (9) |
C31 | 0.0235 (11) | 0.0220 (11) | 0.0256 (12) | 0.0017 (9) | 0.0071 (9) | 0.0030 (9) |
C32 | 0.0253 (11) | 0.0233 (11) | 0.0274 (12) | −0.0005 (9) | 0.0040 (9) | 0.0067 (9) |
C33 | 0.0228 (11) | 0.0301 (13) | 0.0323 (13) | 0.0032 (9) | 0.0067 (10) | 0.0041 (10) |
C34 | 0.0285 (12) | 0.0329 (13) | 0.0274 (13) | −0.0001 (10) | 0.0087 (10) | 0.0050 (10) |
C35 | 0.0302 (12) | 0.0242 (12) | 0.0272 (13) | −0.0036 (10) | 0.0032 (10) | 0.0056 (9) |
C36 | 0.0264 (12) | 0.0251 (12) | 0.0304 (13) | 0.0033 (9) | 0.0048 (9) | 0.0071 (9) |
C37 | 0.0239 (11) | 0.0312 (13) | 0.0275 (12) | 0.0035 (10) | 0.0041 (9) | 0.0074 (10) |
C38 | 0.0452 (16) | 0.0371 (15) | 0.0242 (13) | −0.0022 (12) | −0.0012 (11) | 0.0041 (11) |
C39 | 0.0363 (15) | 0.0492 (17) | 0.0354 (15) | 0.0141 (13) | 0.0006 (12) | 0.0127 (13) |
C40 | 0.0363 (14) | 0.0387 (14) | 0.0270 (13) | −0.0013 (11) | 0.0016 (10) | 0.0086 (11) |
O1—N1 | 1.226 (3) | O4—N5 | 1.218 (3) |
O2—N1 | 1.222 (3) | O5—N5 | 1.220 (3) |
O3—C11 | 1.376 (3) | O6—C31 | 1.379 (3) |
O3—C10 | 1.433 (3) | O6—C30 | 1.429 (3) |
N1—C1 | 1.473 (3) | N5—C21 | 1.474 (3) |
N2—C8 | 1.339 (3) | N6—N7 | 1.340 (3) |
N2—N3 | 1.343 (3) | N6—C28 | 1.341 (3) |
N2—C7 | 1.467 (3) | N6—C27 | 1.468 (3) |
N3—N4 | 1.316 (3) | N7—N8 | 1.316 (3) |
N4—C9 | 1.353 (3) | N8—C29 | 1.360 (3) |
C1—C2 | 1.378 (3) | C21—C22 | 1.376 (3) |
C1—C6 | 1.380 (3) | C21—C26 | 1.387 (3) |
C2—C3 | 1.390 (3) | C22—C23 | 1.391 (3) |
C2—H2 | 0.9500 | C22—H22 | 0.9500 |
C3—C4 | 1.390 (3) | C23—C24 | 1.389 (3) |
C3—H3 | 0.9500 | C23—H23 | 0.9500 |
C4—C5 | 1.388 (3) | C24—C25 | 1.387 (3) |
C4—C7 | 1.514 (3) | C24—C27 | 1.513 (3) |
C5—C6 | 1.389 (3) | C25—C26 | 1.385 (3) |
C5—H5 | 0.9500 | C25—H25 | 0.9500 |
C6—H6 | 0.9500 | C26—H26 | 0.9500 |
C7—H7A | 0.9900 | C27—H27A | 0.9900 |
C7—H7B | 0.9900 | C27—H27B | 0.9900 |
C8—C9 | 1.367 (3) | C28—C29 | 1.368 (3) |
C8—H8 | 0.9500 | C28—H28 | 0.9500 |
C9—C10 | 1.487 (3) | C29—C30 | 1.487 (3) |
C10—H10A | 0.9900 | C30—H30A | 0.9900 |
C10—H10B | 0.9900 | C30—H30B | 0.9900 |
C11—C16 | 1.388 (4) | C31—C36 | 1.386 (3) |
C11—C12 | 1.406 (3) | C31—C32 | 1.412 (3) |
C12—C13 | 1.392 (3) | C32—C33 | 1.388 (3) |
C12—C17 | 1.523 (3) | C32—C37 | 1.520 (3) |
C13—C14 | 1.390 (4) | C33—C34 | 1.393 (4) |
C13—H13 | 0.9500 | C33—H33 | 0.9500 |
C14—C15 | 1.388 (4) | C34—C35 | 1.388 (4) |
C14—H14 | 0.9500 | C34—H34 | 0.9500 |
C15—C16 | 1.395 (4) | C35—C36 | 1.394 (3) |
C15—C20 | 1.506 (4) | C35—C40 | 1.506 (4) |
C16—H16 | 0.9500 | C36—H36 | 0.9500 |
C17—C18 | 1.526 (3) | C37—C39 | 1.525 (4) |
C17—C19 | 1.530 (4) | C37—C38 | 1.531 (4) |
C17—H17 | 1.0000 | C37—H37 | 1.0000 |
C18—H18A | 0.9800 | C38—H38A | 0.9800 |
C18—H18B | 0.9800 | C38—H38B | 0.9800 |
C18—H18C | 0.9800 | C38—H38C | 0.9800 |
C19—H19A | 0.9800 | C39—H39A | 0.9800 |
C19—H19B | 0.9800 | C39—H39B | 0.9800 |
C19—H19C | 0.9800 | C39—H39C | 0.9800 |
C20—H20A | 0.9800 | C40—H40A | 0.9800 |
C20—H20B | 0.9800 | C40—H40B | 0.9800 |
C20—H20C | 0.9800 | C40—H40C | 0.9800 |
C11—O3—C10 | 116.88 (18) | C31—O6—C30 | 116.70 (18) |
O2—N1—O1 | 123.4 (2) | O4—N5—O5 | 123.7 (2) |
O2—N1—C1 | 118.3 (2) | O4—N5—C21 | 118.2 (2) |
O1—N1—C1 | 118.2 (2) | O5—N5—C21 | 118.1 (2) |
C8—N2—N3 | 111.29 (19) | N7—N6—C28 | 111.59 (19) |
C8—N2—C7 | 127.9 (2) | N7—N6—C27 | 120.4 (2) |
N3—N2—C7 | 120.77 (19) | C28—N6—C27 | 128.1 (2) |
N4—N3—N2 | 106.60 (19) | N8—N7—N6 | 106.76 (19) |
N3—N4—C9 | 109.07 (19) | N7—N8—C29 | 108.79 (19) |
C2—C1—C6 | 123.0 (2) | C22—C21—C26 | 122.8 (2) |
C2—C1—N1 | 118.4 (2) | C22—C21—N5 | 118.7 (2) |
C6—C1—N1 | 118.6 (2) | C26—C21—N5 | 118.5 (2) |
C1—C2—C3 | 118.0 (2) | C21—C22—C23 | 118.4 (2) |
C1—C2—H2 | 121.0 | C21—C22—H22 | 120.8 |
C3—C2—H2 | 121.0 | C23—C22—H22 | 120.8 |
C2—C3—C4 | 120.4 (2) | C24—C23—C22 | 120.4 (2) |
C2—C3—H3 | 119.8 | C24—C23—H23 | 119.8 |
C4—C3—H3 | 119.8 | C22—C23—H23 | 119.8 |
C5—C4—C3 | 120.1 (2) | C25—C24—C23 | 119.6 (2) |
C5—C4—C7 | 119.9 (2) | C25—C24—C27 | 120.1 (2) |
C3—C4—C7 | 119.9 (2) | C23—C24—C27 | 120.2 (2) |
C4—C5—C6 | 120.1 (2) | C26—C25—C24 | 121.0 (2) |
C4—C5—H5 | 119.9 | C26—C25—H25 | 119.5 |
C6—C5—H5 | 119.9 | C24—C25—H25 | 119.5 |
C1—C6—C5 | 118.3 (2) | C25—C26—C21 | 117.8 (2) |
C1—C6—H6 | 120.8 | C25—C26—H26 | 121.1 |
C5—C6—H6 | 120.8 | C21—C26—H26 | 121.1 |
N2—C7—C4 | 111.59 (18) | N6—C27—C24 | 111.66 (18) |
N2—C7—H7A | 109.3 | N6—C27—H27A | 109.3 |
C4—C7—H7A | 109.3 | C24—C27—H27A | 109.3 |
N2—C7—H7B | 109.3 | N6—C27—H27B | 109.3 |
C4—C7—H7B | 109.3 | C24—C27—H27B | 109.3 |
H7A—C7—H7B | 108.0 | H27A—C27—H27B | 107.9 |
N2—C8—C9 | 104.7 (2) | N6—C28—C29 | 104.4 (2) |
N2—C8—H8 | 127.7 | N6—C28—H28 | 127.8 |
C9—C8—H8 | 127.7 | C29—C28—H28 | 127.8 |
N4—C9—C8 | 108.4 (2) | N8—C29—C28 | 108.4 (2) |
N4—C9—C10 | 123.1 (2) | N8—C29—C30 | 122.7 (2) |
C8—C9—C10 | 128.5 (2) | C28—C29—C30 | 128.9 (2) |
O3—C10—C9 | 107.65 (19) | O6—C30—C29 | 107.88 (19) |
O3—C10—H10A | 110.2 | O6—C30—H30A | 110.1 |
C9—C10—H10A | 110.2 | C29—C30—H30A | 110.1 |
O3—C10—H10B | 110.2 | O6—C30—H30B | 110.1 |
C9—C10—H10B | 110.2 | C29—C30—H30B | 110.1 |
H10A—C10—H10B | 108.5 | H30A—C30—H30B | 108.4 |
O3—C11—C16 | 123.7 (2) | O6—C31—C36 | 123.8 (2) |
O3—C11—C12 | 114.8 (2) | O6—C31—C32 | 114.8 (2) |
C16—C11—C12 | 121.4 (2) | C36—C31—C32 | 121.5 (2) |
C13—C12—C11 | 116.6 (2) | C33—C32—C31 | 116.4 (2) |
C13—C12—C17 | 123.5 (2) | C33—C32—C37 | 123.7 (2) |
C11—C12—C17 | 119.9 (2) | C31—C32—C37 | 119.9 (2) |
C14—C13—C12 | 122.1 (2) | C32—C33—C34 | 122.2 (2) |
C14—C13—H13 | 119.0 | C32—C33—H33 | 118.9 |
C12—C13—H13 | 119.0 | C34—C33—H33 | 118.9 |
C15—C14—C13 | 120.9 (2) | C35—C34—C33 | 120.8 (2) |
C15—C14—H14 | 119.6 | C35—C34—H34 | 119.6 |
C13—C14—H14 | 119.6 | C33—C34—H34 | 119.6 |
C14—C15—C16 | 117.9 (2) | C34—C35—C36 | 117.9 (2) |
C14—C15—C20 | 122.5 (2) | C34—C35—C40 | 122.2 (2) |
C16—C15—C20 | 119.6 (2) | C36—C35—C40 | 120.0 (2) |
C11—C16—C15 | 121.1 (2) | C31—C36—C35 | 121.2 (2) |
C11—C16—H16 | 119.5 | C31—C36—H36 | 119.4 |
C15—C16—H16 | 119.5 | C35—C36—H36 | 119.4 |
C12—C17—C18 | 113.6 (2) | C32—C37—C39 | 113.5 (2) |
C12—C17—C19 | 110.4 (2) | C32—C37—C38 | 110.7 (2) |
C18—C17—C19 | 110.1 (2) | C39—C37—C38 | 110.2 (2) |
C12—C17—H17 | 107.5 | C32—C37—H37 | 107.4 |
C18—C17—H17 | 107.5 | C39—C37—H37 | 107.4 |
C19—C17—H17 | 107.5 | C38—C37—H37 | 107.4 |
C17—C18—H18A | 109.5 | C37—C38—H38A | 109.5 |
C17—C18—H18B | 109.5 | C37—C38—H38B | 109.5 |
H18A—C18—H18B | 109.5 | H38A—C38—H38B | 109.5 |
C17—C18—H18C | 109.5 | C37—C38—H38C | 109.5 |
H18A—C18—H18C | 109.5 | H38A—C38—H38C | 109.5 |
H18B—C18—H18C | 109.5 | H38B—C38—H38C | 109.5 |
C17—C19—H19A | 109.5 | C37—C39—H39A | 109.5 |
C17—C19—H19B | 109.5 | C37—C39—H39B | 109.5 |
H19A—C19—H19B | 109.5 | H39A—C39—H39B | 109.5 |
C17—C19—H19C | 109.5 | C37—C39—H39C | 109.5 |
H19A—C19—H19C | 109.5 | H39A—C39—H39C | 109.5 |
H19B—C19—H19C | 109.5 | H39B—C39—H39C | 109.5 |
C15—C20—H20A | 109.5 | C35—C40—H40A | 109.5 |
C15—C20—H20B | 109.5 | C35—C40—H40B | 109.5 |
H20A—C20—H20B | 109.5 | H40A—C40—H40B | 109.5 |
C15—C20—H20C | 109.5 | C35—C40—H40C | 109.5 |
H20A—C20—H20C | 109.5 | H40A—C40—H40C | 109.5 |
H20B—C20—H20C | 109.5 | H40B—C40—H40C | 109.5 |
C8—N2—N3—N4 | −0.2 (3) | C28—N6—N7—N8 | 0.5 (3) |
C7—N2—N3—N4 | 179.00 (19) | C27—N6—N7—N8 | −179.72 (19) |
N2—N3—N4—C9 | 0.7 (3) | N6—N7—N8—C29 | −0.6 (3) |
O2—N1—C1—C2 | −2.3 (3) | O4—N5—C21—C22 | −173.7 (3) |
O1—N1—C1—C2 | 178.5 (2) | O5—N5—C21—C22 | 5.2 (4) |
O2—N1—C1—C6 | 176.9 (2) | O4—N5—C21—C26 | 6.4 (4) |
O1—N1—C1—C6 | −2.3 (3) | O5—N5—C21—C26 | −174.7 (2) |
C6—C1—C2—C3 | −0.5 (4) | C26—C21—C22—C23 | 0.5 (4) |
N1—C1—C2—C3 | 178.7 (2) | N5—C21—C22—C23 | −179.3 (2) |
C1—C2—C3—C4 | 0.1 (4) | C21—C22—C23—C24 | 0.0 (4) |
C2—C3—C4—C5 | 0.6 (4) | C22—C23—C24—C25 | −0.7 (4) |
C2—C3—C4—C7 | −179.9 (2) | C22—C23—C24—C27 | 178.6 (2) |
C3—C4—C5—C6 | −0.9 (4) | C23—C24—C25—C26 | 0.8 (4) |
C7—C4—C5—C6 | 179.6 (2) | C27—C24—C25—C26 | −178.5 (2) |
C2—C1—C6—C5 | 0.2 (4) | C24—C25—C26—C21 | −0.2 (4) |
N1—C1—C6—C5 | −179.0 (2) | C22—C21—C26—C25 | −0.5 (4) |
C4—C5—C6—C1 | 0.5 (4) | N5—C21—C26—C25 | 179.4 (2) |
C8—N2—C7—C4 | 98.3 (3) | N7—N6—C27—C24 | 80.7 (3) |
N3—N2—C7—C4 | −80.7 (3) | C25—C24—C27—N6 | −89.4 (3) |
C5—C4—C7—N2 | 88.4 (3) | C23—C24—C27—N6 | 91.3 (3) |
C3—C4—C7—N2 | −91.0 (3) | N7—N6—C28—C29 | −0.2 (3) |
N3—N2—C8—C9 | −0.4 (3) | C27—N6—C28—C29 | −179.9 (2) |
C7—N2—C8—C9 | −179.5 (2) | N7—N8—C29—C28 | 0.5 (3) |
N3—N4—C9—C8 | −0.9 (3) | N7—N8—C29—C30 | −179.0 (2) |
N3—N4—C9—C10 | 179.1 (2) | N6—C28—C29—N8 | −0.2 (3) |
N2—C8—C9—N4 | 0.8 (3) | N6—C28—C29—C30 | 179.2 (2) |
N2—C8—C9—C10 | −179.2 (2) | C31—O6—C30—C29 | 176.28 (19) |
C11—O3—C10—C9 | −176.57 (19) | N8—C29—C30—O6 | 71.6 (3) |
N4—C9—C10—O3 | −71.7 (3) | C28—C29—C30—O6 | −107.8 (3) |
C8—C9—C10—O3 | 108.3 (3) | C30—O6—C31—C36 | −4.9 (3) |
C10—O3—C11—C16 | 4.6 (3) | C30—O6—C31—C32 | 174.7 (2) |
C10—O3—C11—C12 | −175.4 (2) | O6—C31—C32—C33 | −178.6 (2) |
O3—C11—C12—C13 | 179.0 (2) | C36—C31—C32—C33 | 1.0 (4) |
C16—C11—C12—C13 | −1.0 (4) | O6—C31—C32—C37 | 1.5 (3) |
O3—C11—C12—C17 | −1.4 (3) | C36—C31—C32—C37 | −179.0 (2) |
C16—C11—C12—C17 | 178.6 (2) | C31—C32—C33—C34 | −1.1 (4) |
C11—C12—C13—C14 | 0.9 (4) | C37—C32—C33—C34 | 178.9 (2) |
C17—C12—C13—C14 | −178.7 (2) | C32—C33—C34—C35 | 0.2 (4) |
C12—C13—C14—C15 | −0.2 (4) | C33—C34—C35—C36 | 0.8 (4) |
C13—C14—C15—C16 | −0.4 (4) | C33—C34—C35—C40 | −179.7 (2) |
C13—C14—C15—C20 | 179.4 (2) | O6—C31—C36—C35 | 179.5 (2) |
O3—C11—C16—C15 | −179.6 (2) | C32—C31—C36—C35 | 0.0 (4) |
C12—C11—C16—C15 | 0.4 (4) | C34—C35—C36—C31 | −0.9 (4) |
C14—C15—C16—C11 | 0.3 (4) | C40—C35—C36—C31 | 179.6 (2) |
C20—C15—C16—C11 | −179.5 (2) | C33—C32—C37—C39 | 19.6 (3) |
C13—C12—C17—C18 | −19.9 (4) | C31—C32—C37—C39 | −160.4 (2) |
C11—C12—C17—C18 | 160.5 (2) | C33—C32—C37—C38 | −104.8 (3) |
C13—C12—C17—C19 | 104.3 (3) | C31—C32—C37—C38 | 75.1 (3) |
C11—C12—C17—C19 | −75.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···N8 | 0.95 | 2.43 | 3.300 (3) | 151 |
C28—H28···N4i | 0.95 | 2.45 | 3.305 (3) | 149 |
C5—H5···O4ii | 0.95 | 2.55 | 3.466 (3) | 161 |
C25—H25···O1iii | 0.95 | 2.56 | 3.330 (3) | 138 |
Symmetry codes: (i) x, y−1, z; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z. |
Acknowledgements
The support of NSF-MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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