organic compounds
Ethyl 2-(6-nitro-1H-indazol-1-yl)acetate
aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Mohammed V University, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: mmohamedabdelahi@gmail.com
The 11H11N3O4, comprises two independent molecules, both of which display positional disorder of their ethyl chains in 0.868 (4):0.132 (4) and 0.839 (4):0.161 (4) ratios. The packing is directed by a combination of C—H⋯O hydrogen bonds and N—O⋯π interactions between nitro groups and the aromatic rings.
of the title compound, CKeywords: crystal structure; hydrogen bonds; indazole.
CCDC reference: 1538788
Structure description
As a continuation of our studies of N-substituted indazole derivatives and their potential pharmacological activities (Boulhaoua et al., 2016; Mohamed Abdelahi et al., 2017), we now describe the synthesis and structure of the title compound.
The ). The dihedral angle between the five- and six-membered rings making up the imidazole rings are 1.12 (3)° in the molecule containing N1 and N2 and 1.28 (3)° in the other. In both molecules, the ethyl groups are approximately 15% disordered.
comprises two independent molecules differing primarily in the orientations of the ester groups (Fig. 1The packing is directed by a combination of C—H⋯O hydrogen bonds (Table 1) and N—O⋯π contacts between nitro groups and the six-membered rings of the indazole moieties. Fig. 1 shows the C8—H8A⋯O5 hydrogen bond occurring within the as well as the N3—O3⋯π(C12–C17 ring) interaction [O⋯π = 3.131 (1) Å, N—O⋯π = 102.81 (9)°] The second N—O⋯π interaction occurs between N6—O7 and the centroid of the C1–C6 ring at x, y, z + 1 [O⋯π = 3.14 (1) Å, N—O⋯π = 109.16 (9)°]. The combination of hydrogen bonds and N—O⋯π interactions leads to a layer structure parallel to (100) (Figs. 2 and 3).
Synthesis and crystallization
To a solution of 6-nitro-1H-indazole (1 g, 5 mmol) in THF (30 ml) was added ethyl bromoacetate (0.8 g, 5 mmol), potassium carbonate (1.24 g, 9 mmol) and a catalytic quantity of tetra-n-butylammonium iodide. The mixture was stirred at room temperature for 48 h. The solution was filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol solution to afford the title compound as yellow crystals (yield: 66%).
Refinement
Crystal and . The ethyl groups (C10, C11 and C21 C22) are disordered over two sites in 0.868 (4):0.132 (4) and 0.839 (4):0.161 (4) ratios, respectively. The components of the disorder were refined subject to restraints that their geometries be comparable and with the attached H atoms included as riding contributions in idealized positions. The largest peak in the final difference map (0.73 e-Å−3) is 0.86 Å from O4 and suggests a slight (< 9%) disorder in this nitro group, which is also suggested by the elongation of the displacement ellipsoid towards the residual peak. However, the rest of this group does not show such indications so it was decided to not include disorder here in the final refinement.
details appear in Table 2
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Structural data
CCDC reference: 1538788
https://doi.org/10.1107/S2414314617004321/hb4127sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617004321/hb4127Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617004321/hb4127Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617004321/hb4127Isup4.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); 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).C11H11N3O4 | F(000) = 1040 |
Mr = 249.23 | Dx = 1.474 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.6867 (6) Å | Cell parameters from 9337 reflections |
b = 21.7492 (10) Å | θ = 2.5–29.1° |
c = 8.1393 (4) Å | µ = 0.12 mm−1 |
β = 90.772 (1)° | T = 100 K |
V = 2245.64 (18) Å3 | Block, colourless |
Z = 8 | 0.36 × 0.34 × 0.29 mm |
Bruker SMART APEX CCD diffractometer | 6063 independent reflections |
Radiation source: fine-focus sealed tube | 5118 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 29.2°, θmin = 1.6° |
φ and ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −29→29 |
Tmin = 0.88, Tmax = 0.97 | l = −11→11 |
43057 measured reflections |
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)] = 0.051 | Hydrogen site location: mixed |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0762P)2 + 1.075P] where P = (Fo2 + 2Fc2)/3 |
6063 reflections | (Δ/σ)max = 0.001 |
387 parameters | Δρmax = 0.73 e Å−3 |
4 restraints | Δρmin = −0.49 e Å−3 |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 15 sec/frame. |
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. The ethyl groups (C10, C11, C21 & C22) are disordered over two sites in 87:13 and 84:16 ratios, respectively. The components of the disorder were refined subject to restraints that their geometries be comparable and with the attached H-atoms included as riding contributions in idealized positions. The largest peak in the final difference map (0.73 e-Å-3) is 0.86 Å from O4 and suggests a slight (< 9%) disorder in this nitro group which is also suggested by the elongation of the displacement ellipsoid towards the residual peak. However, the rest of this group does not show such indications so it was decided to not include a disorder here in the final refinement. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.81992 (8) | 0.42860 (5) | −0.12528 (12) | 0.0269 (2) | |
O2 | 0.77563 (9) | 0.35022 (5) | 0.04235 (14) | 0.0322 (3) | |
O3 | 0.64535 (9) | 0.62390 (5) | 0.38381 (12) | 0.0283 (2) | |
O4 | 0.65775 (14) | 0.71177 (5) | 0.26110 (16) | 0.0495 (4) | |
N1 | 0.60290 (10) | 0.47079 (6) | −0.27310 (14) | 0.0245 (3) | |
N2 | 0.61891 (9) | 0.47588 (5) | −0.10760 (13) | 0.0208 (2) | |
N3 | 0.64742 (10) | 0.65568 (6) | 0.25929 (15) | 0.0268 (3) | |
C1 | 0.62452 (10) | 0.53588 (6) | −0.05982 (15) | 0.0182 (2) | |
C2 | 0.63799 (10) | 0.56187 (6) | 0.09626 (15) | 0.0192 (2) | |
H2 | 0.6457 (15) | 0.5377 (8) | 0.190 (2) | 0.029 (4)* | |
C3 | 0.63737 (11) | 0.62513 (6) | 0.09891 (16) | 0.0208 (3) | |
C4 | 0.62617 (12) | 0.66290 (6) | −0.04148 (17) | 0.0241 (3) | |
H4 | 0.6349 (16) | 0.7053 (9) | −0.030 (2) | 0.037 (5)* | |
C5 | 0.61171 (11) | 0.63610 (6) | −0.19303 (16) | 0.0233 (3) | |
H5 | 0.6059 (16) | 0.6620 (9) | −0.289 (3) | 0.041 (5)* | |
C6 | 0.60950 (10) | 0.57158 (6) | −0.20334 (16) | 0.0206 (3) | |
C7 | 0.59634 (11) | 0.52741 (6) | −0.33084 (17) | 0.0236 (3) | |
H7 | 0.5823 (14) | 0.5319 (8) | −0.443 (2) | 0.027 (4)* | |
C8 | 0.64448 (11) | 0.42197 (6) | −0.01384 (16) | 0.0219 (3) | |
H8A | 0.6341 (15) | 0.4315 (8) | 0.102 (2) | 0.028 (5)* | |
H8B | 0.5976 (15) | 0.3883 (9) | −0.042 (2) | 0.031 (5)* | |
C9 | 0.75746 (11) | 0.40195 (6) | −0.04133 (16) | 0.0224 (3) | |
C10 | 0.88276 (14) | 0.32649 (10) | 0.0339 (3) | 0.0346 (6) | 0.868 (4) |
H10A | 0.9031 | 0.3064 | 0.1387 | 0.041* | 0.868 (4) |
H10B | 0.9330 | 0.3603 | 0.0126 | 0.041* | 0.868 (4) |
C11 | 0.88417 (17) | 0.28034 (10) | −0.1055 (3) | 0.0441 (5) | 0.868 (4) |
H11A | 0.9552 | 0.2632 | −0.1154 | 0.066* | 0.868 (4) |
H11B | 0.8342 | 0.2471 | −0.0829 | 0.066* | 0.868 (4) |
H11C | 0.8640 | 0.3008 | −0.2085 | 0.066* | 0.868 (4) |
C10A | 0.8696 (10) | 0.3149 (8) | 0.0016 (18) | 0.0346 (6) | 0.132 (4) |
H10C | 0.9307 | 0.3420 | −0.0189 | 0.041* | 0.132 (4) |
H10D | 0.8572 | 0.2881 | −0.0950 | 0.041* | 0.132 (4) |
C11A | 0.8842 (11) | 0.2779 (6) | 0.1580 (18) | 0.0441 (5) | 0.132 (4) |
H11D | 0.9462 | 0.2513 | 0.1481 | 0.066* | 0.132 (4) |
H11E | 0.8943 | 0.3059 | 0.2513 | 0.066* | 0.132 (4) |
H11F | 0.8215 | 0.2525 | 0.1759 | 0.066* | 0.132 (4) |
O5 | 0.67001 (8) | 0.42925 (5) | 0.37686 (12) | 0.0295 (2) | |
O6 | 0.71450 (8) | 0.35019 (5) | 0.54310 (14) | 0.0292 (2) | |
O7 | 0.86504 (9) | 0.62072 (5) | 0.88507 (12) | 0.0294 (2) | |
O8 | 0.88491 (12) | 0.70869 (5) | 0.76740 (15) | 0.0436 (3) | |
N4 | 0.88917 (10) | 0.46774 (6) | 0.22757 (14) | 0.0262 (3) | |
N5 | 0.87470 (10) | 0.47329 (5) | 0.39238 (13) | 0.0224 (2) | |
N6 | 0.87448 (10) | 0.65280 (6) | 0.76228 (15) | 0.0263 (3) | |
C12 | 0.87643 (10) | 0.53326 (6) | 0.44106 (15) | 0.0195 (2) | |
C13 | 0.86738 (10) | 0.55951 (6) | 0.59710 (16) | 0.0205 (3) | |
H13 | 0.8557 (15) | 0.5355 (9) | 0.695 (2) | 0.031 (5)* | |
C14 | 0.87669 (11) | 0.62260 (6) | 0.60066 (16) | 0.0217 (3) | |
C15 | 0.89048 (11) | 0.66004 (7) | 0.46108 (17) | 0.0246 (3) | |
H15 | 0.8910 (15) | 0.7031 (9) | 0.475 (2) | 0.034 (5)* | |
C16 | 0.89977 (11) | 0.63290 (7) | 0.30910 (17) | 0.0246 (3) | |
H16 | 0.9084 (15) | 0.6583 (9) | 0.213 (2) | 0.033 (5)* | |
C17 | 0.89463 (10) | 0.56863 (6) | 0.29821 (16) | 0.0218 (3) | |
C18 | 0.90165 (12) | 0.52423 (7) | 0.17054 (17) | 0.0254 (3) | |
H18 | 0.9121 (14) | 0.5306 (8) | 0.053 (2) | 0.028 (4)* | |
C19 | 0.84767 (11) | 0.41988 (6) | 0.48619 (17) | 0.0228 (3) | |
H19A | 0.8913 (15) | 0.3865 (8) | 0.454 (2) | 0.029 (5)* | |
H19B | 0.8583 (15) | 0.4300 (8) | 0.599 (2) | 0.031 (5)* | |
C20 | 0.73319 (11) | 0.40177 (6) | 0.45991 (16) | 0.0228 (3) | |
C21 | 0.60636 (16) | 0.3281 (2) | 0.5411 (7) | 0.0356 (9) | 0.839 (4) |
H21A | 0.5859 | 0.3144 | 0.4292 | 0.043* | 0.839 (4) |
H21B | 0.5578 | 0.3613 | 0.5747 | 0.043* | 0.839 (4) |
C22 | 0.60087 (18) | 0.27658 (10) | 0.6565 (3) | 0.0471 (6) | 0.839 (4) |
H22A | 0.5287 | 0.2605 | 0.6581 | 0.071* | 0.839 (4) |
H22B | 0.6491 | 0.2440 | 0.6218 | 0.071* | 0.839 (4) |
H22C | 0.6211 | 0.2907 | 0.7668 | 0.071* | 0.839 (4) |
C21A | 0.6069 (5) | 0.3291 (13) | 0.515 (5) | 0.0356 (9) | 0.161 (4) |
H21C | 0.5626 | 0.3635 | 0.4748 | 0.043* | 0.161 (4) |
H21D | 0.5770 | 0.3140 | 0.6197 | 0.043* | 0.161 (4) |
C22A | 0.6082 (10) | 0.2795 (5) | 0.3940 (17) | 0.0471 (6) | 0.161 (4) |
H22D | 0.5362 | 0.2648 | 0.3741 | 0.071* | 0.161 (4) |
H22E | 0.6375 | 0.2949 | 0.2911 | 0.071* | 0.161 (4) |
H22F | 0.6519 | 0.2456 | 0.4356 | 0.071* | 0.161 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0284 (5) | 0.0334 (5) | 0.0190 (5) | −0.0052 (4) | 0.0020 (4) | 0.0006 (4) |
O2 | 0.0282 (5) | 0.0275 (5) | 0.0409 (6) | 0.0012 (4) | 0.0003 (4) | 0.0103 (5) |
O3 | 0.0321 (5) | 0.0345 (6) | 0.0182 (5) | −0.0012 (4) | 0.0016 (4) | −0.0021 (4) |
O4 | 0.0907 (11) | 0.0236 (6) | 0.0339 (6) | 0.0080 (6) | −0.0098 (7) | −0.0083 (5) |
N1 | 0.0312 (6) | 0.0272 (6) | 0.0149 (5) | −0.0031 (5) | −0.0008 (4) | −0.0021 (4) |
N2 | 0.0284 (6) | 0.0195 (5) | 0.0144 (5) | −0.0010 (4) | 0.0000 (4) | −0.0002 (4) |
N3 | 0.0322 (6) | 0.0256 (6) | 0.0224 (6) | 0.0041 (5) | −0.0016 (5) | −0.0048 (4) |
C1 | 0.0180 (6) | 0.0199 (6) | 0.0168 (6) | −0.0002 (4) | 0.0009 (4) | 0.0002 (4) |
C2 | 0.0192 (6) | 0.0222 (6) | 0.0162 (5) | 0.0015 (5) | 0.0006 (4) | 0.0001 (5) |
C3 | 0.0226 (6) | 0.0225 (6) | 0.0174 (6) | 0.0021 (5) | −0.0002 (5) | −0.0025 (5) |
C4 | 0.0284 (7) | 0.0191 (6) | 0.0247 (7) | 0.0030 (5) | −0.0001 (5) | 0.0015 (5) |
C5 | 0.0269 (7) | 0.0229 (6) | 0.0201 (6) | 0.0032 (5) | −0.0010 (5) | 0.0047 (5) |
C6 | 0.0213 (6) | 0.0234 (6) | 0.0170 (6) | 0.0010 (5) | −0.0007 (4) | 0.0014 (5) |
C7 | 0.0271 (7) | 0.0270 (7) | 0.0166 (6) | −0.0014 (5) | −0.0017 (5) | 0.0004 (5) |
C8 | 0.0280 (7) | 0.0190 (6) | 0.0188 (6) | −0.0020 (5) | 0.0022 (5) | 0.0019 (5) |
C9 | 0.0270 (7) | 0.0216 (6) | 0.0185 (6) | −0.0030 (5) | −0.0020 (5) | −0.0010 (5) |
C10 | 0.0264 (9) | 0.0316 (11) | 0.0456 (13) | 0.0033 (8) | −0.0056 (8) | 0.0035 (8) |
C11 | 0.0350 (10) | 0.0347 (10) | 0.0628 (14) | 0.0049 (8) | 0.0066 (9) | 0.0013 (9) |
C10A | 0.0264 (9) | 0.0316 (11) | 0.0456 (13) | 0.0033 (8) | −0.0056 (8) | 0.0035 (8) |
C11A | 0.0350 (10) | 0.0347 (10) | 0.0628 (14) | 0.0049 (8) | 0.0066 (9) | 0.0013 (9) |
O5 | 0.0282 (5) | 0.0416 (6) | 0.0187 (5) | 0.0091 (4) | −0.0018 (4) | −0.0010 (4) |
O6 | 0.0242 (5) | 0.0247 (5) | 0.0387 (6) | −0.0009 (4) | −0.0010 (4) | 0.0017 (4) |
O7 | 0.0349 (6) | 0.0348 (6) | 0.0186 (5) | −0.0003 (4) | 0.0004 (4) | −0.0011 (4) |
O8 | 0.0711 (9) | 0.0262 (6) | 0.0336 (6) | −0.0073 (6) | 0.0047 (6) | −0.0067 (5) |
N4 | 0.0318 (6) | 0.0309 (6) | 0.0158 (5) | 0.0047 (5) | 0.0009 (4) | −0.0017 (4) |
N5 | 0.0287 (6) | 0.0236 (6) | 0.0150 (5) | 0.0018 (4) | 0.0004 (4) | −0.0003 (4) |
N6 | 0.0286 (6) | 0.0279 (6) | 0.0224 (6) | −0.0026 (5) | 0.0002 (4) | −0.0031 (5) |
C12 | 0.0181 (6) | 0.0236 (6) | 0.0167 (6) | 0.0010 (5) | −0.0008 (4) | 0.0010 (5) |
C13 | 0.0194 (6) | 0.0256 (6) | 0.0165 (6) | −0.0007 (5) | 0.0001 (4) | 0.0013 (5) |
C14 | 0.0212 (6) | 0.0257 (6) | 0.0183 (6) | −0.0007 (5) | −0.0001 (5) | −0.0007 (5) |
C15 | 0.0260 (7) | 0.0237 (6) | 0.0239 (6) | −0.0037 (5) | −0.0016 (5) | 0.0029 (5) |
C16 | 0.0252 (7) | 0.0288 (7) | 0.0198 (6) | −0.0032 (5) | 0.0001 (5) | 0.0059 (5) |
C17 | 0.0203 (6) | 0.0281 (7) | 0.0170 (6) | −0.0001 (5) | 0.0002 (4) | 0.0022 (5) |
C18 | 0.0279 (7) | 0.0318 (7) | 0.0167 (6) | 0.0022 (5) | 0.0019 (5) | 0.0005 (5) |
C19 | 0.0260 (7) | 0.0220 (6) | 0.0205 (6) | 0.0018 (5) | −0.0025 (5) | 0.0016 (5) |
C20 | 0.0258 (6) | 0.0247 (6) | 0.0178 (6) | 0.0041 (5) | 0.0008 (5) | −0.0047 (5) |
C21 | 0.0257 (7) | 0.0354 (8) | 0.046 (3) | −0.0060 (6) | 0.0007 (7) | −0.0052 (12) |
C22 | 0.0375 (11) | 0.0325 (10) | 0.0713 (16) | −0.0068 (8) | 0.0078 (10) | −0.0046 (10) |
C21A | 0.0257 (7) | 0.0354 (8) | 0.046 (3) | −0.0060 (6) | 0.0007 (7) | −0.0052 (12) |
C22A | 0.0375 (11) | 0.0325 (10) | 0.0713 (16) | −0.0068 (8) | 0.0078 (10) | −0.0046 (10) |
O1—C9 | 1.2023 (17) | O5—C20 | 1.2007 (17) |
O2—C9 | 1.3335 (17) | O6—C20 | 1.3333 (18) |
O2—C10 | 1.456 (2) | O6—C21 | 1.454 (2) |
O2—C10A | 1.460 (3) | O6—C21A | 1.454 (3) |
O3—N3 | 1.2274 (16) | O7—N6 | 1.2261 (16) |
O4—N3 | 1.2270 (17) | O8—N6 | 1.2233 (17) |
N1—C7 | 1.3204 (18) | N4—C18 | 1.3235 (19) |
N1—N2 | 1.3640 (15) | N4—N5 | 1.3617 (15) |
N2—C1 | 1.3632 (16) | N5—C12 | 1.3631 (17) |
N2—C8 | 1.4337 (17) | N5—C19 | 1.4343 (17) |
N3—C3 | 1.4687 (17) | N6—C14 | 1.4710 (17) |
C1—C2 | 1.3988 (17) | C12—C13 | 1.3986 (18) |
C1—C6 | 1.4135 (17) | C12—C17 | 1.4158 (18) |
C2—C3 | 1.3761 (18) | C13—C14 | 1.3776 (19) |
C2—H2 | 0.930 (19) | C13—H13 | 0.97 (2) |
C3—C4 | 1.4129 (18) | C14—C15 | 1.4106 (19) |
C4—C5 | 1.3744 (19) | C15—C16 | 1.377 (2) |
C4—H4 | 0.93 (2) | C15—H15 | 0.94 (2) |
C5—C6 | 1.4059 (18) | C16—C17 | 1.402 (2) |
C5—H5 | 0.96 (2) | C16—H16 | 0.97 (2) |
C6—C7 | 1.4223 (19) | C17—C18 | 1.4223 (19) |
C7—H7 | 0.934 (19) | C18—H18 | 0.975 (19) |
C8—C9 | 1.518 (2) | C19—C20 | 1.517 (2) |
C8—H8A | 0.978 (19) | C19—H19A | 0.952 (19) |
C8—H8B | 0.969 (19) | C19—H19B | 0.95 (2) |
C10—C11 | 1.515 (3) | C21—C22 | 1.464 (7) |
C10—H10A | 0.9900 | C21—H21A | 0.9900 |
C10—H10B | 0.9900 | C21—H21B | 0.9900 |
C11—H11A | 0.9800 | C22—H22A | 0.9800 |
C11—H11B | 0.9800 | C22—H22B | 0.9800 |
C11—H11C | 0.9800 | C22—H22C | 0.9800 |
C10A—C11A | 1.517 (4) | C21A—C22A | 1.464 (8) |
C10A—H10C | 0.9900 | C21A—H21C | 0.9900 |
C10A—H10D | 0.9900 | C21A—H21D | 0.9900 |
C11A—H11D | 0.9800 | C22A—H22D | 0.9800 |
C11A—H11E | 0.9800 | C22A—H22E | 0.9800 |
C11A—H11F | 0.9800 | C22A—H22F | 0.9800 |
C9—O2—C10 | 115.45 (14) | C20—O6—C21 | 116.5 (3) |
C9—O2—C10A | 117.6 (6) | C20—O6—C21A | 111.1 (18) |
C7—N1—N2 | 106.48 (11) | C18—N4—N5 | 106.36 (11) |
C1—N2—N1 | 111.47 (11) | N4—N5—C12 | 111.67 (11) |
C1—N2—C8 | 128.34 (11) | N4—N5—C19 | 119.28 (11) |
N1—N2—C8 | 119.27 (11) | C12—N5—C19 | 128.55 (11) |
O4—N3—O3 | 123.60 (12) | O8—N6—O7 | 123.33 (13) |
O4—N3—C3 | 117.93 (12) | O8—N6—C14 | 118.08 (12) |
O3—N3—C3 | 118.47 (12) | O7—N6—C14 | 118.56 (12) |
N2—C1—C2 | 130.63 (12) | N5—C12—C13 | 130.79 (12) |
N2—C1—C6 | 106.51 (11) | N5—C12—C17 | 106.46 (11) |
C2—C1—C6 | 122.82 (12) | C13—C12—C17 | 122.70 (12) |
C3—C2—C1 | 114.69 (12) | C14—C13—C12 | 114.69 (12) |
C3—C2—H2 | 123.5 (11) | C14—C13—H13 | 122.3 (11) |
C1—C2—H2 | 121.8 (11) | C12—C13—H13 | 123.0 (11) |
C2—C3—C4 | 124.69 (12) | C13—C14—C15 | 124.72 (12) |
C2—C3—N3 | 117.76 (11) | C13—C14—N6 | 117.45 (12) |
C4—C3—N3 | 117.55 (12) | C15—C14—N6 | 117.81 (12) |
C5—C4—C3 | 119.35 (12) | C16—C15—C14 | 119.28 (13) |
C5—C4—H4 | 121.6 (13) | C16—C15—H15 | 122.0 (12) |
C3—C4—H4 | 118.8 (13) | C14—C15—H15 | 118.7 (12) |
C4—C5—C6 | 118.63 (12) | C15—C16—C17 | 118.66 (12) |
C4—C5—H5 | 119.1 (12) | C15—C16—H16 | 119.7 (11) |
C6—C5—H5 | 122.2 (12) | C17—C16—H16 | 121.6 (11) |
C5—C6—C1 | 119.77 (12) | C16—C17—C12 | 119.86 (12) |
C5—C6—C7 | 136.03 (12) | C16—C17—C18 | 136.04 (12) |
C1—C6—C7 | 104.19 (11) | C12—C17—C18 | 104.10 (12) |
N1—C7—C6 | 111.35 (12) | N4—C18—C17 | 111.41 (12) |
N1—C7—H7 | 117.2 (11) | N4—C18—H18 | 119.5 (10) |
C6—C7—H7 | 131.5 (11) | C17—C18—H18 | 129.1 (10) |
N2—C8—C9 | 111.32 (11) | N5—C19—C20 | 111.74 (11) |
N2—C8—H8A | 108.0 (11) | N5—C19—H19A | 109.1 (11) |
C9—C8—H8A | 110.1 (11) | C20—C19—H19A | 108.9 (11) |
N2—C8—H8B | 111.0 (11) | N5—C19—H19B | 107.1 (11) |
C9—C8—H8B | 109.0 (11) | C20—C19—H19B | 108.6 (12) |
H8A—C8—H8B | 107.4 (15) | H19A—C19—H19B | 111.4 (16) |
O1—C9—O2 | 125.89 (13) | O5—C20—O6 | 125.64 (14) |
O1—C9—C8 | 125.21 (13) | O5—C20—C19 | 125.50 (13) |
O2—C9—C8 | 108.90 (11) | O6—C20—C19 | 108.86 (11) |
O2—C10—C11 | 106.90 (16) | O6—C21—C22 | 107.4 (4) |
O2—C10—H10A | 110.3 | O6—C21—H21A | 110.2 |
C11—C10—H10A | 110.3 | C22—C21—H21A | 110.2 |
O2—C10—H10B | 110.3 | O6—C21—H21B | 110.2 |
C11—C10—H10B | 110.3 | C22—C21—H21B | 110.2 |
H10A—C10—H10B | 108.6 | H21A—C21—H21B | 108.5 |
C10—C11—H11A | 109.5 | C21—C22—H22A | 109.5 |
C10—C11—H11B | 109.5 | C21—C22—H22B | 109.5 |
H11A—C11—H11B | 109.5 | H22A—C22—H22B | 109.5 |
C10—C11—H11C | 109.5 | C21—C22—H22C | 109.5 |
H11A—C11—H11C | 109.5 | H22A—C22—H22C | 109.5 |
H11B—C11—H11C | 109.5 | H22B—C22—H22C | 109.5 |
O2—C10A—C11A | 100.4 (8) | O6—C21A—C22A | 108.5 (9) |
O2—C10A—H10C | 111.7 | O6—C21A—H21C | 110.0 |
C11A—C10A—H10C | 111.7 | C22A—C21A—H21C | 110.0 |
O2—C10A—H10D | 111.7 | O6—C21A—H21D | 110.0 |
C11A—C10A—H10D | 111.7 | C22A—C21A—H21D | 110.0 |
H10C—C10A—H10D | 109.5 | H21C—C21A—H21D | 108.4 |
C10A—C11A—H11D | 109.5 | C21A—C22A—H22D | 109.5 |
C10A—C11A—H11E | 109.5 | C21A—C22A—H22E | 109.5 |
H11D—C11A—H11E | 109.5 | H22D—C22A—H22E | 109.5 |
C10A—C11A—H11F | 109.5 | C21A—C22A—H22F | 109.5 |
H11D—C11A—H11F | 109.5 | H22D—C22A—H22F | 109.5 |
H11E—C11A—H11F | 109.5 | H22E—C22A—H22F | 109.5 |
C7—N1—N2—C1 | −1.11 (16) | C18—N4—N5—C12 | 0.83 (16) |
C7—N1—N2—C8 | −171.01 (12) | C18—N4—N5—C19 | 173.37 (12) |
N1—N2—C1—C2 | 178.65 (13) | N4—N5—C12—C13 | −178.31 (13) |
C8—N2—C1—C2 | −12.6 (2) | C19—N5—C12—C13 | 10.0 (2) |
N1—N2—C1—C6 | 0.96 (15) | N4—N5—C12—C17 | −0.81 (15) |
C8—N2—C1—C6 | 169.71 (13) | C19—N5—C12—C17 | −172.49 (13) |
N2—C1—C2—C3 | −178.47 (13) | N5—C12—C13—C14 | 177.68 (13) |
C6—C1—C2—C3 | −1.11 (19) | C17—C12—C13—C14 | 0.53 (19) |
C1—C2—C3—C4 | −1.1 (2) | C12—C13—C14—C15 | 2.2 (2) |
C1—C2—C3—N3 | 177.93 (11) | C12—C13—C14—N6 | −176.32 (11) |
O4—N3—C3—C2 | 172.69 (14) | O8—N6—C14—C13 | 178.48 (14) |
O3—N3—C3—C2 | −7.12 (19) | O7—N6—C14—C13 | 0.33 (19) |
O4—N3—C3—C4 | −8.2 (2) | O8—N6—C14—C15 | −0.2 (2) |
O3—N3—C3—C4 | 171.97 (13) | O7—N6—C14—C15 | −178.31 (13) |
C2—C3—C4—C5 | 2.0 (2) | C13—C14—C15—C16 | −2.7 (2) |
N3—C3—C4—C5 | −177.05 (13) | N6—C14—C15—C16 | 175.82 (13) |
C3—C4—C5—C6 | −0.6 (2) | C14—C15—C16—C17 | 0.3 (2) |
C4—C5—C6—C1 | −1.5 (2) | C15—C16—C17—C12 | 2.2 (2) |
C4—C5—C6—C7 | 179.59 (15) | C15—C16—C17—C18 | −179.10 (15) |
N2—C1—C6—C5 | −179.67 (12) | N5—C12—C17—C16 | 179.50 (12) |
C2—C1—C6—C5 | 2.4 (2) | C13—C12—C17—C16 | −2.7 (2) |
N2—C1—C6—C7 | −0.43 (14) | N5—C12—C17—C18 | 0.46 (14) |
C2—C1—C6—C7 | −178.35 (12) | C13—C12—C17—C18 | 178.21 (12) |
N2—N1—C7—C6 | 0.81 (16) | N5—N4—C18—C17 | −0.51 (16) |
C5—C6—C7—N1 | 178.80 (15) | C16—C17—C18—N4 | −178.77 (16) |
C1—C6—C7—N1 | −0.24 (16) | C12—C17—C18—N4 | 0.04 (16) |
C1—N2—C8—C9 | −93.57 (16) | N4—N5—C19—C20 | −75.60 (15) |
N1—N2—C8—C9 | 74.42 (15) | C12—N5—C19—C20 | 95.53 (16) |
C10—O2—C9—O1 | 2.6 (2) | C21—O6—C20—O5 | −4.4 (2) |
C10A—O2—C9—O1 | −14.8 (9) | C21A—O6—C20—O5 | 2.4 (8) |
C10—O2—C9—C8 | −177.49 (14) | C21—O6—C20—C19 | 176.02 (17) |
C10A—O2—C9—C8 | 165.1 (9) | C21A—O6—C20—C19 | −177.2 (8) |
N2—C8—C9—O1 | 2.76 (19) | N5—C19—C20—O5 | −2.82 (19) |
N2—C8—C9—O2 | −177.16 (11) | N5—C19—C20—O6 | 176.73 (11) |
C9—O2—C10—C11 | −93.65 (18) | C20—O6—C21—C22 | −172.46 (17) |
C9—O2—C10A—C11A | 158.7 (8) | C20—O6—C21A—C22A | 100 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O4i | 0.93 (2) | 2.50 (2) | 3.1923 (18) | 131.3 (16) |
C7—H7···O3ii | 0.934 (19) | 2.579 (18) | 3.1973 (17) | 124.0 (14) |
C8—H8A···O5 | 0.978 (19) | 2.276 (19) | 3.1960 (17) | 156.4 (15) |
C15—H15···O8i | 0.94 (2) | 2.55 (2) | 3.2616 (18) | 132.0 (16) |
C18—H18···O7ii | 0.975 (19) | 2.461 (18) | 3.1606 (18) | 128.5 (14) |
C19—H19B···O1iii | 0.95 (2) | 2.30 (2) | 3.1923 (17) | 155.2 (16) |
C21—H21B···O3iv | 0.99 | 2.62 | 3.423 (3) | 138 |
C22—H22A···O4iv | 0.98 | 2.54 | 3.367 (3) | 142 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, y, z−1; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+1. |
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
References
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