organic compounds
1-(3-Bromo-6-nitro-1H-indazol-1-yl)ethan-1-one
aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Mohammed V University, Rabat, Morocco, bFaculté des Sciences et Techniques, Université de Sciences, de Technologie, et de Medecine Nouakchott, Mauritania, and cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: mmohamedabdelahi@gmail.com
The 9H6BrN3O3, consists of two independent molecules differing in the rotational orientations of the nitro and acetyl substituents. In the crystal, head-to-head π-stacking between pairs of adjacent molecules forms dimers which are associated into stacks by C—Br⋯π(ring) interactions. C—H⋯O hydrogen bonds tie the stacks together.
of the title compound, CKeywords: crystal structure; hydrogen bond; π-stacking; indazole.
CCDC reference: 1547454
Structure description
Among heterocyclic frameworks, indazole derivatives have been widely used in medicinal chemistry and drug discovery including anti-inflammatory, anti-tumor, or HIV protease inhibition (Boulouard et al., 2007), as well as exhibiting estrogen receptor binding (Steffan et al., 2004), antifungal and antibacterial activities (Tandon et al., 2005). Following this line of research, we now report a new acetylation of 6-nitro-1H-indazole using acetic anhydride in the presence of a catalytic amount of acetic acid.
The ) consists of two independent molecules which differ in the rotational orientations of the nitro and acetyl groups. Thus the C6—C5—N3—O2 and C15—C14—N6—O5 torsion angles are, respectively, 7.1 (2) and 18.8 (2)° while the N2—N1—C8—C9 and N5—N4—C17—C18 torsion angles are, respectively, −0.8 (2) and −1.6 (2)°.
(Fig. 1In the crystal, head-to-head π-stacking between pairs of adjacent molecules [centroid–centroid distance for the five-membered rings = 3.6509 (9) Å and for the six-membered rings = 3.7419 (9) Å, with dihedral angles, respectively, of 1.00 (8) and 1.57 (7)°] forms dimers which are associated into stacks by C1—Br1⋯π(ring) interactions [ring = C10–C16/N4/N5 at − x, + y, − z with Br1⋯centroid = 3.660 (7) Å] (Figs. 2 and 3). The mean planes of the molecules in the stacks are inclined at ±30.19 (1)° to (010). Tying the stacks together are C9—H9B⋯O1 and C13—H13⋯O1 hydrogen bonds (Table 1 and Figs. 2 and 3). Between the stacks are Br1⋯O5(x + , −y + , z − ) and Br2⋯O2(x + , −y + , z − ) contacts of 2.966 (1) and 3.039 (1) Å, respectively, which are significantly less than the sum of the van der Waals radii (3.37 Å) and so may be additional attractive interactions binding the stacks together.
Synthesis and crystallization
A mixture of 3-bromo-6-nitro-1H-indazole (0.6 g, 3.68 mmol), acetic acid (2 ml) and acetic anhydride (10 ml) were heated under reflux for 24 h. After completion of the reaction (monitored by TLC), the solvent was removed under vacuum. The residue obtained was recrystallized from ethanol solution to afford the title compound as colorless crystals (yield 62%; m.p. 429–431 K).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1547454
https://doi.org/10.1107/S2414314617006605/ff4017sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617006605/ff4017Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006605/ff4017Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006605/ff4017Isup4.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).C9H6BrN3O3 | F(000) = 1120 |
Mr = 284.08 | Dx = 1.879 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.9863 (5) Å | Cell parameters from 9129 reflections |
b = 7.8783 (3) Å | θ = 2.8–29.1° |
c = 18.5549 (7) Å | µ = 4.09 mm−1 |
β = 100.786 (1)° | T = 100 K |
V = 2008.41 (13) Å3 | Thick plate, colourless |
Z = 8 | 0.28 × 0.24 × 0.13 mm |
Bruker SMART APEX CCD diffractometer | 5389 independent reflections |
Radiation source: fine-focus sealed tube | 4592 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 29.2°, θmin = 1.7° |
φ and ω scans | h = −19→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −10→10 |
Tmin = 0.52, Tmax = 0.62 | l = −25→25 |
37783 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)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0368P)2 + 0.0704P] where P = (Fo2 + 2Fc2)/3 |
5389 reflections | (Δ/σ)max = 0.002 |
291 parameters | Δρmax = 0.68 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.87667 (2) | 0.69535 (2) | −0.10776 (2) | 0.01973 (5) | |
O1 | 0.82655 (9) | 0.28983 (17) | 0.25598 (7) | 0.0303 (3) | |
O2 | 0.68943 (9) | 0.18565 (17) | 0.20109 (7) | 0.0295 (3) | |
O3 | 0.51681 (8) | 0.32535 (15) | −0.03442 (6) | 0.0206 (2) | |
N1 | 0.65058 (9) | 0.45981 (16) | −0.05561 (7) | 0.0151 (3) | |
N2 | 0.69880 (9) | 0.54546 (16) | −0.10335 (8) | 0.0166 (3) | |
N3 | 0.76125 (10) | 0.27475 (18) | 0.20217 (7) | 0.0195 (3) | |
C1 | 0.78515 (11) | 0.57816 (19) | −0.06524 (9) | 0.0162 (3) | |
C2 | 0.79925 (11) | 0.51742 (19) | 0.00842 (9) | 0.0154 (3) | |
C3 | 0.87569 (11) | 0.5216 (2) | 0.06909 (10) | 0.0189 (3) | |
H3 | 0.9356 | 0.5754 | 0.0663 | 0.023* | |
C4 | 0.86134 (11) | 0.4455 (2) | 0.13281 (9) | 0.0190 (3) | |
H4 | 0.9114 | 0.4462 | 0.1752 | 0.023* | |
C5 | 0.77190 (11) | 0.3665 (2) | 0.13456 (9) | 0.0164 (3) | |
C6 | 0.69405 (11) | 0.36030 (19) | 0.07664 (9) | 0.0153 (3) | |
H6 | 0.6344 | 0.3058 | 0.0800 | 0.018* | |
C7 | 0.70969 (10) | 0.44003 (18) | 0.01304 (9) | 0.0140 (3) | |
C8 | 0.55482 (11) | 0.4010 (2) | −0.07805 (9) | 0.0165 (3) | |
C9 | 0.50905 (12) | 0.4392 (2) | −0.15563 (9) | 0.0213 (4) | |
H9A | 0.5111 | 0.5619 | −0.1641 | 0.032* | |
H9B | 0.4412 | 0.4008 | −0.1649 | 0.032* | |
H9C | 0.5448 | 0.3802 | −0.1888 | 0.032* | |
Br2 | 0.98495 (2) | 0.44610 (2) | 0.64437 (2) | 0.02026 (5) | |
O4 | 0.59044 (10) | 0.35663 (17) | 0.30282 (7) | 0.0320 (3) | |
O5 | 0.51604 (8) | 0.56878 (15) | 0.34207 (7) | 0.0240 (3) | |
O6 | 0.56802 (8) | 0.74041 (15) | 0.59182 (6) | 0.0216 (2) | |
N4 | 0.71797 (9) | 0.62900 (16) | 0.60559 (7) | 0.0149 (3) | |
N5 | 0.80800 (9) | 0.59760 (17) | 0.64970 (7) | 0.0168 (3) | |
N6 | 0.58318 (10) | 0.46593 (17) | 0.34829 (8) | 0.0197 (3) | |
C10 | 0.85715 (11) | 0.5139 (2) | 0.60782 (9) | 0.0167 (3) | |
C11 | 0.80361 (11) | 0.48477 (19) | 0.53549 (9) | 0.0153 (3) | |
C12 | 0.82254 (11) | 0.4017 (2) | 0.47287 (9) | 0.0182 (3) | |
H12 | 0.8841 | 0.3513 | 0.4724 | 0.022* | |
C13 | 0.74902 (12) | 0.3953 (2) | 0.41204 (9) | 0.0190 (3) | |
H13 | 0.7586 | 0.3383 | 0.3688 | 0.023* | |
C14 | 0.65985 (11) | 0.47404 (19) | 0.41478 (9) | 0.0162 (3) | |
C15 | 0.63782 (11) | 0.55937 (18) | 0.47456 (9) | 0.0149 (3) | |
H15 | 0.5766 | 0.6122 | 0.4741 | 0.018* | |
C16 | 0.71298 (11) | 0.56155 (18) | 0.53582 (9) | 0.0140 (3) | |
C17 | 0.64391 (12) | 0.71328 (19) | 0.63304 (9) | 0.0171 (3) | |
C18 | 0.66666 (13) | 0.7624 (2) | 0.71242 (9) | 0.0247 (4) | |
H18A | 0.6780 | 0.6599 | 0.7427 | 0.037* | |
H18B | 0.6117 | 0.8257 | 0.7250 | 0.037* | |
H18C | 0.7251 | 0.8337 | 0.7215 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01677 (8) | 0.01729 (9) | 0.02671 (10) | −0.00333 (5) | 0.00815 (6) | 0.00148 (6) |
O1 | 0.0241 (6) | 0.0447 (8) | 0.0188 (6) | 0.0035 (6) | −0.0042 (5) | 0.0037 (6) |
O2 | 0.0290 (7) | 0.0402 (8) | 0.0199 (7) | −0.0076 (6) | 0.0063 (5) | 0.0019 (6) |
O3 | 0.0156 (5) | 0.0243 (6) | 0.0216 (6) | −0.0061 (4) | 0.0030 (5) | −0.0001 (5) |
N1 | 0.0130 (6) | 0.0174 (6) | 0.0147 (7) | −0.0027 (5) | 0.0017 (5) | −0.0004 (5) |
N2 | 0.0159 (6) | 0.0160 (6) | 0.0187 (7) | −0.0019 (5) | 0.0050 (5) | 0.0005 (5) |
N3 | 0.0209 (7) | 0.0229 (7) | 0.0148 (7) | 0.0062 (5) | 0.0035 (5) | −0.0029 (5) |
C1 | 0.0145 (7) | 0.0135 (7) | 0.0214 (8) | −0.0008 (5) | 0.0055 (6) | −0.0009 (6) |
C2 | 0.0140 (7) | 0.0115 (7) | 0.0211 (8) | −0.0012 (5) | 0.0043 (6) | −0.0025 (6) |
C3 | 0.0125 (7) | 0.0163 (8) | 0.0271 (9) | −0.0020 (6) | 0.0018 (6) | −0.0044 (7) |
C4 | 0.0159 (7) | 0.0194 (8) | 0.0194 (8) | 0.0006 (6) | −0.0027 (6) | −0.0050 (6) |
C5 | 0.0172 (7) | 0.0177 (7) | 0.0146 (8) | 0.0026 (6) | 0.0035 (6) | −0.0019 (6) |
C6 | 0.0136 (7) | 0.0156 (7) | 0.0169 (8) | −0.0009 (5) | 0.0033 (6) | −0.0043 (6) |
C7 | 0.0113 (7) | 0.0141 (7) | 0.0162 (8) | 0.0001 (5) | 0.0013 (5) | −0.0041 (6) |
C8 | 0.0131 (7) | 0.0152 (7) | 0.0201 (8) | −0.0013 (5) | 0.0002 (6) | −0.0034 (6) |
C9 | 0.0185 (8) | 0.0225 (9) | 0.0200 (9) | −0.0034 (6) | −0.0037 (6) | 0.0014 (7) |
Br2 | 0.01229 (8) | 0.02216 (9) | 0.02581 (10) | 0.00376 (5) | 0.00225 (6) | 0.00464 (6) |
O4 | 0.0401 (8) | 0.0345 (7) | 0.0196 (7) | 0.0146 (6) | 0.0012 (6) | −0.0089 (6) |
O5 | 0.0254 (6) | 0.0250 (6) | 0.0200 (6) | 0.0103 (5) | 0.0005 (5) | −0.0011 (5) |
O6 | 0.0177 (6) | 0.0283 (6) | 0.0192 (6) | 0.0081 (5) | 0.0046 (5) | 0.0004 (5) |
N4 | 0.0130 (6) | 0.0168 (6) | 0.0147 (7) | 0.0031 (5) | 0.0023 (5) | 0.0005 (5) |
N5 | 0.0126 (6) | 0.0184 (6) | 0.0186 (7) | 0.0020 (5) | 0.0007 (5) | 0.0030 (5) |
N6 | 0.0240 (7) | 0.0208 (7) | 0.0155 (7) | 0.0039 (5) | 0.0063 (5) | 0.0015 (5) |
C10 | 0.0131 (7) | 0.0144 (7) | 0.0227 (8) | 0.0015 (5) | 0.0036 (6) | 0.0042 (6) |
C11 | 0.0133 (7) | 0.0135 (7) | 0.0205 (8) | 0.0014 (5) | 0.0071 (6) | 0.0042 (6) |
C12 | 0.0167 (7) | 0.0159 (7) | 0.0240 (9) | 0.0048 (6) | 0.0085 (6) | 0.0040 (6) |
C13 | 0.0232 (8) | 0.0165 (7) | 0.0197 (8) | 0.0039 (6) | 0.0106 (6) | 0.0019 (6) |
C14 | 0.0190 (8) | 0.0154 (7) | 0.0149 (8) | 0.0016 (6) | 0.0047 (6) | 0.0024 (6) |
C15 | 0.0138 (7) | 0.0140 (7) | 0.0178 (8) | 0.0026 (5) | 0.0051 (6) | 0.0033 (6) |
C16 | 0.0151 (7) | 0.0124 (7) | 0.0160 (8) | 0.0010 (5) | 0.0067 (6) | 0.0020 (6) |
C17 | 0.0182 (7) | 0.0159 (7) | 0.0189 (8) | 0.0032 (6) | 0.0075 (6) | 0.0031 (6) |
C18 | 0.0249 (9) | 0.0326 (9) | 0.0168 (8) | 0.0076 (7) | 0.0041 (7) | −0.0025 (7) |
Br1—C1 | 1.8686 (15) | Br2—C10 | 1.8673 (15) |
O1—N3 | 1.2264 (18) | O4—N6 | 1.2230 (18) |
O2—N3 | 1.2226 (19) | O5—N6 | 1.2293 (17) |
O3—C8 | 1.2060 (19) | O6—C17 | 1.205 (2) |
N1—N2 | 1.3850 (18) | N4—C16 | 1.389 (2) |
N1—C7 | 1.3914 (19) | N4—N5 | 1.3896 (17) |
N1—C8 | 1.4047 (19) | N4—C17 | 1.4039 (19) |
N2—C1 | 1.306 (2) | N5—C10 | 1.308 (2) |
N3—C5 | 1.479 (2) | N6—C14 | 1.477 (2) |
C1—C2 | 1.427 (2) | C10—C11 | 1.428 (2) |
C2—C3 | 1.400 (2) | C11—C12 | 1.401 (2) |
C2—C7 | 1.410 (2) | C11—C16 | 1.405 (2) |
C3—C4 | 1.374 (2) | C12—C13 | 1.378 (2) |
C3—H3 | 0.9500 | C12—H12 | 0.9500 |
C4—C5 | 1.403 (2) | C13—C14 | 1.402 (2) |
C4—H4 | 0.9500 | C13—H13 | 0.9500 |
C5—C6 | 1.380 (2) | C14—C15 | 1.380 (2) |
C6—C7 | 1.390 (2) | C15—C16 | 1.396 (2) |
C6—H6 | 0.9500 | C15—H15 | 0.9500 |
C8—C9 | 1.492 (2) | C17—C18 | 1.498 (2) |
C9—H9A | 0.9800 | C18—H18A | 0.9800 |
C9—H9B | 0.9800 | C18—H18B | 0.9800 |
C9—H9C | 0.9800 | C18—H18C | 0.9800 |
N2—N1—C7 | 111.28 (12) | C16—N4—N5 | 111.27 (12) |
N2—N1—C8 | 121.50 (13) | C16—N4—C17 | 127.40 (13) |
C7—N1—C8 | 127.21 (13) | N5—N4—C17 | 121.28 (13) |
C1—N2—N1 | 105.16 (13) | C10—N5—N4 | 105.00 (13) |
O2—N3—O1 | 123.59 (15) | O4—N6—O5 | 124.05 (14) |
O2—N3—C5 | 118.66 (13) | O4—N6—C14 | 117.76 (13) |
O1—N3—C5 | 117.73 (14) | O5—N6—C14 | 118.19 (13) |
N2—C1—C2 | 113.62 (14) | N5—C10—C11 | 113.45 (13) |
N2—C1—Br1 | 120.40 (12) | N5—C10—Br2 | 120.15 (12) |
C2—C1—Br1 | 125.98 (11) | C11—C10—Br2 | 126.40 (12) |
C3—C2—C7 | 120.97 (15) | C12—C11—C16 | 121.00 (15) |
C3—C2—C1 | 135.25 (15) | C12—C11—C10 | 135.01 (14) |
C7—C2—C1 | 103.78 (13) | C16—C11—C10 | 103.98 (14) |
C4—C3—C2 | 117.98 (15) | C13—C12—C11 | 117.92 (14) |
C4—C3—H3 | 121.0 | C13—C12—H12 | 121.0 |
C2—C3—H3 | 121.0 | C11—C12—H12 | 121.0 |
C3—C4—C5 | 119.21 (15) | C12—C13—C14 | 119.11 (15) |
C3—C4—H4 | 120.4 | C12—C13—H13 | 120.4 |
C5—C4—H4 | 120.4 | C14—C13—H13 | 120.4 |
C6—C5—C4 | 125.08 (15) | C15—C14—C13 | 125.34 (15) |
C6—C5—N3 | 116.94 (14) | C15—C14—N6 | 117.13 (13) |
C4—C5—N3 | 117.91 (14) | C13—C14—N6 | 117.53 (14) |
C5—C6—C7 | 114.74 (14) | C14—C15—C16 | 114.38 (14) |
C5—C6—H6 | 122.6 | C14—C15—H15 | 122.8 |
C7—C6—H6 | 122.6 | C16—C15—H15 | 122.8 |
C6—C7—N1 | 131.83 (13) | N4—C16—C15 | 131.46 (14) |
C6—C7—C2 | 121.99 (14) | N4—C16—C11 | 106.29 (13) |
N1—C7—C2 | 106.16 (13) | C15—C16—C11 | 122.23 (14) |
O3—C8—N1 | 118.65 (14) | O6—C17—N4 | 118.39 (15) |
O3—C8—C9 | 125.73 (14) | O6—C17—C18 | 125.29 (15) |
N1—C8—C9 | 115.62 (14) | N4—C17—C18 | 116.33 (14) |
C8—C9—H9A | 109.5 | C17—C18—H18A | 109.5 |
C8—C9—H9B | 109.5 | C17—C18—H18B | 109.5 |
H9A—C9—H9B | 109.5 | H18A—C18—H18B | 109.5 |
C8—C9—H9C | 109.5 | C17—C18—H18C | 109.5 |
H9A—C9—H9C | 109.5 | H18A—C18—H18C | 109.5 |
H9B—C9—H9C | 109.5 | H18B—C18—H18C | 109.5 |
C7—N1—N2—C1 | −0.18 (16) | C16—N4—N5—C10 | 0.38 (17) |
C8—N1—N2—C1 | −178.96 (13) | C17—N4—N5—C10 | 178.10 (14) |
N1—N2—C1—C2 | 0.07 (17) | N4—N5—C10—C11 | −0.39 (18) |
N1—N2—C1—Br1 | −179.62 (10) | N4—N5—C10—Br2 | 179.26 (10) |
N2—C1—C2—C3 | −179.36 (17) | N5—C10—C11—C12 | −178.64 (17) |
Br1—C1—C2—C3 | 0.3 (3) | Br2—C10—C11—C12 | 1.7 (3) |
N2—C1—C2—C7 | 0.06 (18) | N5—C10—C11—C16 | 0.26 (18) |
Br1—C1—C2—C7 | 179.73 (11) | Br2—C10—C11—C16 | −179.37 (11) |
C7—C2—C3—C4 | 1.1 (2) | C16—C11—C12—C13 | −1.0 (2) |
C1—C2—C3—C4 | −179.55 (17) | C10—C11—C12—C13 | 177.75 (17) |
C2—C3—C4—C5 | 0.3 (2) | C11—C12—C13—C14 | 1.2 (2) |
C3—C4—C5—C6 | −1.0 (2) | C12—C13—C14—C15 | −0.3 (3) |
C3—C4—C5—N3 | 175.56 (14) | C12—C13—C14—N6 | 179.42 (14) |
O2—N3—C5—C6 | 7.1 (2) | O4—N6—C14—C15 | −161.03 (15) |
O1—N3—C5—C6 | −174.45 (14) | O5—N6—C14—C15 | 18.8 (2) |
O2—N3—C5—C4 | −169.81 (14) | O4—N6—C14—C13 | 19.2 (2) |
O1—N3—C5—C4 | 8.7 (2) | O5—N6—C14—C13 | −160.94 (15) |
C4—C5—C6—C7 | 0.2 (2) | C13—C14—C15—C16 | −0.7 (2) |
N3—C5—C6—C7 | −176.44 (13) | N6—C14—C15—C16 | 179.57 (13) |
C5—C6—C7—N1 | 179.54 (15) | N5—N4—C16—C15 | 178.78 (15) |
C5—C6—C7—C2 | 1.3 (2) | C17—N4—C16—C15 | 1.2 (3) |
N2—N1—C7—C6 | −178.20 (15) | N5—N4—C16—C11 | −0.23 (16) |
C8—N1—C7—C6 | 0.5 (3) | C17—N4—C16—C11 | −177.78 (14) |
N2—N1—C7—C2 | 0.22 (16) | C14—C15—C16—N4 | −178.02 (15) |
C8—N1—C7—C2 | 178.91 (14) | C14—C15—C16—C11 | 0.8 (2) |
C3—C2—C7—C6 | −2.0 (2) | C12—C11—C16—N4 | 179.09 (14) |
C1—C2—C7—C6 | 178.45 (14) | C10—C11—C16—N4 | −0.01 (16) |
C3—C2—C7—N1 | 179.36 (13) | C12—C11—C16—C15 | 0.0 (2) |
C1—C2—C7—N1 | −0.17 (16) | C10—C11—C16—C15 | −179.13 (14) |
N2—N1—C8—O3 | 179.09 (14) | C16—N4—C17—O6 | −4.3 (2) |
C7—N1—C8—O3 | 0.5 (2) | N5—N4—C17—O6 | 178.37 (14) |
N2—N1—C8—C9 | −0.8 (2) | C16—N4—C17—C18 | 175.71 (15) |
C7—N1—C8—C9 | −179.40 (14) | N5—N4—C17—C18 | −1.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···O1i | 0.98 | 2.47 | 3.301 (2) | 142 |
C13—H13···O1 | 0.95 | 2.49 | 3.380 (2) | 157 |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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