organic compounds
3-Chloro-6-nitro-1-[(1-octyl-1H-1,2,3-triazol-4-yl)methyl]-1H-indazole
aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: dedah6211672@gmail.com
The 18H23ClN6O2, consists of two independent molecules differing primarily in the dihedral angles between the mean planes of the indazole and triazole moieties [78.50 (8) in one and 72.39 (7)° in the other]. One of the molecules shows positional disorder of the terminal part of its octyl chain. In the crystal, C—H⋯X (X = Cl, N, O) hydrogen bonds and C—H⋯π and π-stacking interactions are observed: together these generate a three-dimensional network.
of the title compound, CKeywords: crystal structure; indazole; triazole; hydrogen bond; π-stacking; crystal structure.
CCDC reference: 1529978
Structure description
As a continuation of our studies of indazole derivatives (Boulhaoua et al., 2016), we report the synthesis and structure of the title compound.
The ). The primary differences between the two are a disorder in the C34–C35–C36 portion of one alkyl chain and different dihedral angles between the mean planes of the indazole and triazole rings, being 78.50 (8)° in the molecule containing Cl1 and 72.39 (7)° in the other.
of the title compound consists of two independent molecules having very similar conformations and so an ellipsoid plot of only one molecule is shown (Fig. 1As shown in Fig. 2, there are a number of different intermolecular interactions. The C—H⋯X (X = Cl, N, O) hydrogen bonds as well as the C—H⋯π(ring) interactions are listed in Table 1. In addition there are π–π stacking interactions between centrosymmetrically related indazole units [Cg1⋯Cg3 = 3.636 (2) Å, dihedral angle 0.53 (14)°]. The result is a three-dimensional supramolecular network (Fig. 3) in which the long alkyl chains tend to intercalate but the segregation of `head' and `tail' portions is not as pronounced as in related molecules (Boulhaoua et al., 2016).
Synthesis and crystallization
To a solution of 3-chloro-6-nitro-1-(prop-2-yn-1-yl)-1H-indazole (0.3 g, 1.27 mmol) in ethanol (15 ml) was added 1-azidooctane (0.24 g, 1.53 mmol). The mixture was stirred under reflux for 48 h. After completion of reaction (monitored by TLC), the solution was concentrated and the residue was purified by on silica gel by using a mixture (hexane/ethyl acetate 9/1). Crystals were obtained when the solvent was allowed to evaporate. The solid product was purified by recrystallization from ethanol solution to afford colourless crystals in 70% yield.
Refinement
Crystal data, data collection and structure . Carbon atoms C34–C36 are disordered over two closely spaced sites in a 0.52 (2):0.48 (2) ratio. The components of the disorder were refined subject to restraints that their geometries approximate that of the corresponding portion of the ordered alkyl chain. The hydrogen atoms attached to the disordered atoms were included as riding contributions in idealized positions. Trial refinements with the single-component data extracted from the full data set with TWINABS (Sheldrick, 2009) and with the full three-component data indicated that the former was superior.
details are summarized in Table 2
|
Structural data
CCDC reference: 1529978
https://doi.org/10.1107/S2414314617001468/hb4116sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001468/hb4116Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617001468/hb4116Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617001468/hb4116Isup4.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).C18H23ClN6O2 | F(000) = 1648 |
Mr = 390.87 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 25.3512 (9) Å | Cell parameters from 9411 reflections |
b = 14.9091 (5) Å | θ = 3.6–70.1° |
c = 10.7525 (3) Å | µ = 1.91 mm−1 |
β = 101.725 (2)° | T = 150 K |
V = 3979.3 (2) Å3 | Plate, colourless |
Z = 8 | 0.12 × 0.12 × 0.02 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 7460 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 5327 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.068 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 70.2°, θmin = 3.5° |
ω scans | h = −30→30 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −17→18 |
Tmin = 0.80, Tmax = 0.96 | l = −13→12 |
22444 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)] = 0.058 | Hydrogen site location: mixed |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0372P)2 + 1.7954P] where P = (Fo2 + 2Fc2)/3 |
7460 reflections | (Δ/σ)max = 0.001 |
653 parameters | Δρmax = 0.19 e Å−3 |
10 restraints | Δρmin = −0.28 e Å−3 |
Experimental. Analysis of 2946 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 monoclinic system and to consist of at least three components. With approximately 90% of the reflections indexed with the three major components, it was decided to use these for the structure determination. The raw data were processed using the multi-component version of SAINT under control of the three-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. Carbons C34-C36 are disordered over two closely spaced sites in a 52:48 ratio. The components of the disorder were refined subject to restraints that their geometries approximate that of the corresponding portion of the ordered alkyl chain. The hydrogen atoms attached to the disordered atoms were included as riding contributions in idealized positions. Trial refinements with the single-component data extracted from the full data set with TWINABS and with the full 3-component data indicated that the former refinement was superior. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 1.06482 (3) | −0.05492 (5) | 0.71585 (6) | 0.0410 (2) | |
O1 | 1.08776 (9) | 0.06599 (14) | 0.0520 (2) | 0.0495 (6) | |
O2 | 1.04771 (9) | −0.05912 (13) | −0.00830 (17) | 0.0420 (5) | |
N1 | 1.02266 (9) | −0.17337 (15) | 0.54180 (19) | 0.0297 (5) | |
N2 | 1.01686 (9) | −0.18696 (14) | 0.41414 (19) | 0.0261 (5) | |
N3 | 1.06707 (9) | −0.00487 (16) | 0.0742 (2) | 0.0332 (6) | |
N4 | 0.85290 (9) | −0.19184 (14) | 0.17346 (19) | 0.0289 (5) | |
N5 | 0.84521 (10) | −0.18829 (17) | 0.2940 (2) | 0.0377 (6) | |
N6 | 0.89099 (10) | −0.21181 (16) | 0.3684 (2) | 0.0350 (6) | |
C1 | 1.03835 (10) | −0.11787 (16) | 0.3578 (2) | 0.0238 (6) | |
C2 | 1.04026 (10) | −0.10374 (17) | 0.2305 (2) | 0.0254 (6) | |
H2 | 1.0265 (10) | −0.1453 (18) | 0.163 (2) | 0.032 (7)* | |
C3 | 1.06481 (11) | −0.02509 (17) | 0.2070 (2) | 0.0272 (6) | |
C4 | 1.08714 (11) | 0.03768 (19) | 0.3007 (3) | 0.0311 (6) | |
H4 | 1.1042 (11) | 0.0894 (19) | 0.274 (3) | 0.038 (8)* | |
C5 | 1.08466 (11) | 0.02235 (19) | 0.4247 (3) | 0.0312 (6) | |
H5 | 1.0981 (11) | 0.0650 (18) | 0.487 (3) | 0.031 (7)* | |
C6 | 1.05969 (10) | −0.05621 (17) | 0.4539 (2) | 0.0262 (6) | |
C7 | 1.04850 (11) | −0.09668 (18) | 0.5652 (2) | 0.0288 (6) | |
C8 | 0.98327 (11) | −0.25993 (18) | 0.3518 (3) | 0.0295 (6) | |
H8A | 0.9824 (11) | −0.3072 (19) | 0.415 (3) | 0.040 (8)* | |
H8B | 1.0020 (11) | −0.2874 (17) | 0.289 (3) | 0.036 (8)* | |
C9 | 0.92765 (10) | −0.23026 (16) | 0.2950 (2) | 0.0256 (6) | |
C10 | 0.90359 (11) | −0.21735 (17) | 0.1714 (2) | 0.0289 (6) | |
H10 | 0.9156 (11) | −0.2263 (18) | 0.096 (3) | 0.040 (8)* | |
C11 | 0.80896 (12) | −0.1697 (2) | 0.0677 (3) | 0.0350 (7) | |
H11A | 0.7751 (12) | −0.2037 (19) | 0.081 (3) | 0.043 (8)* | |
H11B | 0.8189 (10) | −0.1895 (17) | −0.014 (3) | 0.033 (7)* | |
C12 | 0.79522 (12) | −0.0710 (2) | 0.0601 (3) | 0.0356 (7) | |
H12A | 0.8262 (12) | −0.037 (2) | 0.050 (3) | 0.045 (9)* | |
H12B | 0.7866 (11) | −0.0526 (18) | 0.143 (3) | 0.038 (8)* | |
C13 | 0.74781 (13) | −0.0525 (2) | −0.0495 (3) | 0.0376 (7) | |
H13A | 0.7182 (12) | −0.091 (2) | −0.033 (3) | 0.045 (9)* | |
H13B | 0.7571 (12) | −0.0748 (19) | −0.135 (3) | 0.049 (9)* | |
C14 | 0.73000 (14) | 0.0451 (2) | −0.0636 (3) | 0.0412 (7) | |
H14A | 0.7609 (13) | 0.084 (2) | −0.085 (3) | 0.052 (9)* | |
H14B | 0.6973 (13) | 0.050 (2) | −0.137 (3) | 0.053 (9)* | |
C15 | 0.71683 (13) | 0.0848 (2) | 0.0577 (3) | 0.0400 (7) | |
H15A | 0.6948 (12) | 0.036 (2) | 0.098 (3) | 0.055 (9)* | |
H15B | 0.7512 (13) | 0.094 (2) | 0.123 (3) | 0.058 (10)* | |
C16 | 0.68594 (13) | 0.1729 (2) | 0.0359 (3) | 0.0414 (7) | |
H16A | 0.6491 (11) | 0.1608 (18) | −0.026 (3) | 0.035 (8)* | |
H16B | 0.7052 (13) | 0.219 (2) | −0.011 (3) | 0.054 (9)* | |
C17 | 0.67661 (14) | 0.2152 (2) | 0.1587 (3) | 0.0484 (8) | |
H17A | 0.6599 (12) | 0.169 (2) | 0.205 (3) | 0.044 (9)* | |
H17B | 0.7125 (14) | 0.229 (2) | 0.219 (3) | 0.056 (10)* | |
C18 | 0.64275 (17) | 0.2996 (2) | 0.1374 (4) | 0.0583 (10) | |
H18A | 0.6599 (16) | 0.351 (3) | 0.089 (4) | 0.089 (13)* | |
H18B | 0.6072 (16) | 0.289 (2) | 0.078 (4) | 0.078 (13)* | |
H18C | 0.6357 (17) | 0.325 (3) | 0.218 (4) | 0.104 (15)* | |
Cl2 | 0.56098 (3) | 0.42012 (5) | 0.81890 (6) | 0.03704 (19) | |
O3 | 0.59263 (10) | 0.54356 (14) | 0.16175 (19) | 0.0541 (6) | |
O4 | 0.53884 (9) | 0.43426 (13) | 0.09351 (17) | 0.0422 (5) | |
N7 | 0.51073 (9) | 0.31204 (14) | 0.63903 (19) | 0.0279 (5) | |
N8 | 0.50277 (8) | 0.30233 (14) | 0.50996 (18) | 0.0253 (5) | |
N9 | 0.56383 (10) | 0.48075 (15) | 0.1790 (2) | 0.0343 (6) | |
N10 | 0.33838 (9) | 0.29026 (14) | 0.26015 (19) | 0.0275 (5) | |
N11 | 0.33042 (10) | 0.29952 (16) | 0.3790 (2) | 0.0347 (6) | |
N12 | 0.37630 (9) | 0.28032 (15) | 0.45646 (19) | 0.0304 (5) | |
C19 | 0.52779 (10) | 0.36914 (16) | 0.4569 (2) | 0.0237 (6) | |
C20 | 0.53062 (11) | 0.38525 (18) | 0.3310 (2) | 0.0262 (6) | |
H20 | 0.5130 (10) | 0.3491 (16) | 0.264 (2) | 0.022 (7)* | |
C21 | 0.55916 (11) | 0.46036 (17) | 0.3111 (2) | 0.0266 (6) | |
C22 | 0.58479 (11) | 0.51830 (18) | 0.4076 (2) | 0.0274 (6) | |
H22 | 0.6046 (11) | 0.5697 (19) | 0.388 (3) | 0.038 (8)* | |
C23 | 0.58208 (11) | 0.50056 (18) | 0.5310 (2) | 0.0268 (6) | |
H23 | 0.5977 (10) | 0.5392 (16) | 0.594 (2) | 0.021 (7)* | |
C24 | 0.55317 (10) | 0.42522 (17) | 0.5560 (2) | 0.0246 (6) | |
C25 | 0.54078 (10) | 0.38417 (17) | 0.6656 (2) | 0.0260 (6) | |
C26 | 0.46897 (11) | 0.22959 (18) | 0.4453 (3) | 0.0283 (6) | |
H26A | 0.4689 (11) | 0.1842 (19) | 0.507 (3) | 0.042 (8)* | |
H26B | 0.4874 (11) | 0.2060 (17) | 0.380 (3) | 0.032 (7)* | |
C27 | 0.41350 (10) | 0.25869 (16) | 0.3862 (2) | 0.0244 (6) | |
C28 | 0.38949 (11) | 0.26531 (18) | 0.2614 (2) | 0.0289 (6) | |
H28 | 0.3989 (11) | 0.2544 (17) | 0.184 (3) | 0.034 (7)* | |
C29 | 0.29440 (12) | 0.3054 (2) | 0.1510 (3) | 0.0321 (6) | |
H29A | 0.2593 (13) | 0.295 (2) | 0.177 (3) | 0.063 (10)* | |
H29B | 0.3003 (11) | 0.2555 (19) | 0.086 (3) | 0.042 (8)* | |
C30 | 0.29403 (14) | 0.3990 (2) | 0.0970 (3) | 0.0419 (8) | |
H30A | 0.2884 (13) | 0.444 (2) | 0.159 (3) | 0.058 (10)* | |
H30B | 0.3310 (12) | 0.4134 (18) | 0.073 (3) | 0.038 (8)* | |
C31 | 0.24855 (14) | 0.4069 (2) | −0.0213 (3) | 0.0468 (8) | |
H31A | 0.2146 (15) | 0.385 (2) | 0.001 (3) | 0.069 (11)* | |
H31B | 0.2576 (13) | 0.364 (2) | −0.094 (3) | 0.062 (10)* | |
C32 | 0.24006 (16) | 0.5007 (2) | −0.0759 (4) | 0.0534 (9) | |
H32A | 0.2791 (15) | 0.523 (2) | −0.103 (3) | 0.075 (11)* | |
H32B | 0.2112 (16) | 0.500 (2) | −0.159 (4) | 0.080 (12)* | |
C33 | 0.22209 (16) | 0.5683 (2) | 0.0135 (4) | 0.0559 (9) | |
H33A | 0.1953 (14) | 0.535 (2) | 0.064 (3) | 0.072 (11)* | |
H33B | 0.2549 (15) | 0.586 (2) | 0.089 (4) | 0.078 (12)* | |
C34A | 0.1940 (16) | 0.6549 (15) | −0.0388 (19) | 0.056 (3) | 0.52 (2) |
H34A | 0.2176 | 0.6867 | −0.0873 | 0.068* | 0.52 (2) |
H34B | 0.1604 | 0.6389 | −0.0995 | 0.068* | 0.52 (2) |
C35A | 0.1797 (11) | 0.7196 (13) | 0.0590 (17) | 0.066 (3) | 0.52 (2) |
H35A | 0.1592 | 0.6867 | 0.1137 | 0.079* | 0.52 (2) |
H35B | 0.2134 | 0.7417 | 0.1138 | 0.079* | 0.52 (2) |
C36A | 0.1466 (8) | 0.7993 (10) | 0.000 (2) | 0.087 (5) | 0.52 (2) |
H36A | 0.1388 | 0.8382 | 0.0678 | 0.130* | 0.52 (2) |
H36B | 0.1670 | 0.8332 | −0.0523 | 0.130* | 0.52 (2) |
H36C | 0.1128 | 0.7782 | −0.0524 | 0.130* | 0.52 (2) |
C34B | 0.1972 (17) | 0.6467 (17) | −0.069 (2) | 0.056 (3) | 0.48 (2) |
H34C | 0.2249 | 0.6747 | −0.1097 | 0.068* | 0.48 (2) |
H34D | 0.1679 | 0.6244 | −0.1374 | 0.068* | 0.48 (2) |
C35B | 0.1749 (12) | 0.7166 (15) | 0.0098 (17) | 0.066 (3) | 0.48 (2) |
H35C | 0.1484 | 0.6874 | 0.0527 | 0.079* | 0.48 (2) |
H35D | 0.2046 | 0.7396 | 0.0764 | 0.079* | 0.48 (2) |
C36B | 0.1480 (9) | 0.7950 (11) | −0.068 (2) | 0.087 (5) | 0.48 (2) |
H36D | 0.1345 | 0.8374 | −0.0123 | 0.130* | 0.48 (2) |
H36E | 0.1742 | 0.8252 | −0.1093 | 0.130* | 0.48 (2) |
H36F | 0.1178 | 0.7730 | −0.1329 | 0.130* | 0.48 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0475 (5) | 0.0555 (5) | 0.0194 (3) | 0.0032 (4) | 0.0054 (3) | −0.0071 (3) |
O1 | 0.0690 (16) | 0.0420 (13) | 0.0445 (13) | −0.0062 (11) | 0.0281 (11) | 0.0091 (10) |
O2 | 0.0612 (15) | 0.0426 (13) | 0.0248 (10) | 0.0021 (10) | 0.0150 (10) | −0.0014 (9) |
N1 | 0.0326 (14) | 0.0387 (14) | 0.0182 (11) | 0.0047 (10) | 0.0064 (10) | 0.0010 (10) |
N2 | 0.0313 (13) | 0.0288 (12) | 0.0186 (11) | −0.0016 (10) | 0.0057 (9) | 0.0004 (9) |
N3 | 0.0377 (15) | 0.0358 (14) | 0.0296 (13) | 0.0102 (11) | 0.0149 (11) | 0.0077 (11) |
N4 | 0.0318 (14) | 0.0329 (13) | 0.0222 (11) | −0.0010 (10) | 0.0062 (10) | −0.0010 (9) |
N5 | 0.0368 (15) | 0.0553 (16) | 0.0226 (12) | −0.0002 (12) | 0.0097 (11) | −0.0026 (11) |
N6 | 0.0363 (15) | 0.0466 (15) | 0.0237 (12) | 0.0001 (11) | 0.0101 (11) | −0.0014 (10) |
C1 | 0.0254 (15) | 0.0253 (14) | 0.0209 (13) | 0.0025 (11) | 0.0049 (11) | −0.0001 (11) |
C2 | 0.0287 (15) | 0.0271 (15) | 0.0210 (13) | 0.0055 (11) | 0.0068 (11) | −0.0014 (11) |
C3 | 0.0321 (16) | 0.0280 (15) | 0.0233 (13) | 0.0063 (12) | 0.0101 (12) | 0.0034 (11) |
C4 | 0.0319 (17) | 0.0289 (15) | 0.0336 (15) | 0.0032 (12) | 0.0092 (13) | 0.0024 (12) |
C5 | 0.0320 (17) | 0.0290 (16) | 0.0313 (15) | 0.0025 (12) | 0.0034 (13) | −0.0082 (13) |
C6 | 0.0269 (15) | 0.0304 (15) | 0.0212 (13) | 0.0060 (11) | 0.0045 (11) | −0.0023 (11) |
C7 | 0.0294 (16) | 0.0381 (16) | 0.0190 (13) | 0.0077 (12) | 0.0050 (11) | −0.0018 (11) |
C8 | 0.0382 (17) | 0.0253 (15) | 0.0263 (14) | 0.0003 (12) | 0.0094 (13) | 0.0001 (12) |
C9 | 0.0343 (16) | 0.0231 (13) | 0.0215 (13) | −0.0024 (11) | 0.0108 (12) | 0.0002 (11) |
C10 | 0.0361 (17) | 0.0292 (15) | 0.0240 (14) | −0.0008 (12) | 0.0120 (12) | −0.0006 (11) |
C11 | 0.0355 (18) | 0.0412 (18) | 0.0271 (15) | 0.0029 (14) | 0.0034 (13) | −0.0023 (13) |
C12 | 0.0325 (18) | 0.0405 (18) | 0.0337 (16) | −0.0003 (14) | 0.0067 (13) | 0.0020 (13) |
C13 | 0.0388 (19) | 0.0395 (18) | 0.0334 (16) | 0.0008 (14) | 0.0044 (14) | 0.0028 (13) |
C14 | 0.039 (2) | 0.0444 (19) | 0.0408 (18) | 0.0004 (15) | 0.0092 (16) | 0.0059 (15) |
C15 | 0.0365 (19) | 0.0447 (19) | 0.0383 (17) | 0.0018 (15) | 0.0068 (15) | 0.0027 (14) |
C16 | 0.0348 (19) | 0.0390 (19) | 0.050 (2) | −0.0025 (14) | 0.0077 (16) | 0.0006 (15) |
C17 | 0.040 (2) | 0.052 (2) | 0.052 (2) | 0.0006 (16) | 0.0043 (17) | −0.0060 (17) |
C18 | 0.053 (3) | 0.049 (2) | 0.072 (3) | 0.0042 (19) | 0.011 (2) | −0.017 (2) |
Cl2 | 0.0440 (4) | 0.0484 (4) | 0.0182 (3) | −0.0063 (3) | 0.0051 (3) | −0.0048 (3) |
O3 | 0.0823 (18) | 0.0465 (13) | 0.0381 (12) | −0.0204 (12) | 0.0230 (12) | 0.0045 (10) |
O4 | 0.0610 (15) | 0.0438 (13) | 0.0227 (10) | −0.0034 (10) | 0.0107 (10) | −0.0030 (9) |
N7 | 0.0299 (13) | 0.0349 (13) | 0.0181 (11) | 0.0030 (10) | 0.0034 (9) | −0.0009 (9) |
N8 | 0.0286 (13) | 0.0281 (12) | 0.0185 (10) | −0.0006 (9) | 0.0032 (9) | −0.0006 (9) |
N9 | 0.0481 (16) | 0.0316 (13) | 0.0261 (12) | 0.0028 (11) | 0.0140 (12) | 0.0012 (11) |
N10 | 0.0284 (13) | 0.0343 (13) | 0.0200 (11) | −0.0004 (10) | 0.0058 (10) | −0.0027 (9) |
N11 | 0.0373 (15) | 0.0448 (15) | 0.0240 (12) | −0.0020 (11) | 0.0108 (11) | −0.0047 (10) |
N12 | 0.0304 (14) | 0.0406 (14) | 0.0209 (11) | −0.0043 (10) | 0.0067 (10) | −0.0013 (10) |
C19 | 0.0213 (14) | 0.0259 (14) | 0.0234 (13) | 0.0055 (11) | 0.0033 (11) | 0.0005 (11) |
C20 | 0.0285 (16) | 0.0288 (15) | 0.0203 (13) | 0.0040 (12) | 0.0022 (12) | −0.0030 (11) |
C21 | 0.0333 (16) | 0.0274 (14) | 0.0204 (13) | 0.0060 (12) | 0.0087 (11) | 0.0019 (11) |
C22 | 0.0286 (16) | 0.0245 (15) | 0.0302 (14) | 0.0006 (12) | 0.0088 (12) | 0.0011 (12) |
C23 | 0.0265 (16) | 0.0287 (15) | 0.0246 (14) | 0.0018 (11) | 0.0040 (12) | −0.0047 (12) |
C24 | 0.0241 (15) | 0.0279 (14) | 0.0217 (13) | 0.0041 (11) | 0.0044 (11) | −0.0012 (11) |
C25 | 0.0291 (15) | 0.0329 (15) | 0.0158 (12) | 0.0028 (12) | 0.0041 (11) | −0.0005 (11) |
C26 | 0.0333 (16) | 0.0254 (15) | 0.0256 (14) | −0.0007 (12) | 0.0042 (12) | −0.0020 (12) |
C27 | 0.0319 (16) | 0.0205 (13) | 0.0222 (13) | −0.0026 (11) | 0.0086 (11) | −0.0002 (10) |
C28 | 0.0319 (17) | 0.0351 (16) | 0.0208 (14) | −0.0004 (12) | 0.0079 (12) | −0.0014 (12) |
C29 | 0.0265 (17) | 0.0405 (17) | 0.0280 (15) | 0.0034 (13) | 0.0027 (12) | −0.0005 (13) |
C30 | 0.046 (2) | 0.0394 (19) | 0.0379 (18) | 0.0046 (15) | 0.0015 (15) | 0.0012 (14) |
C31 | 0.048 (2) | 0.049 (2) | 0.0387 (18) | 0.0039 (17) | −0.0029 (16) | 0.0066 (16) |
C32 | 0.055 (2) | 0.050 (2) | 0.050 (2) | 0.0029 (17) | −0.0013 (19) | 0.0088 (17) |
C33 | 0.052 (2) | 0.043 (2) | 0.067 (2) | 0.0033 (17) | −0.001 (2) | 0.0090 (18) |
C34A | 0.039 (4) | 0.040 (4) | 0.085 (8) | −0.002 (3) | 0.000 (7) | 0.011 (6) |
C35A | 0.039 (4) | 0.046 (3) | 0.110 (10) | −0.005 (3) | 0.006 (9) | −0.001 (7) |
C36A | 0.043 (3) | 0.048 (3) | 0.162 (16) | 0.002 (2) | 0.006 (10) | 0.014 (8) |
C34B | 0.039 (4) | 0.040 (4) | 0.085 (8) | −0.002 (3) | 0.000 (7) | 0.011 (6) |
C35B | 0.039 (4) | 0.046 (3) | 0.110 (10) | −0.005 (3) | 0.006 (9) | −0.001 (7) |
C36B | 0.043 (3) | 0.048 (3) | 0.162 (16) | 0.002 (2) | 0.006 (10) | 0.014 (8) |
Cl1—C7 | 1.706 (3) | N8—C19 | 1.366 (3) |
O1—N3 | 1.224 (3) | N8—C26 | 1.467 (3) |
O2—N3 | 1.227 (3) | N9—C21 | 1.480 (3) |
N1—C7 | 1.316 (3) | N10—N11 | 1.340 (3) |
N1—N2 | 1.366 (3) | N10—C28 | 1.346 (3) |
N2—C1 | 1.364 (3) | N10—C29 | 1.463 (3) |
N2—C8 | 1.458 (3) | N11—N12 | 1.317 (3) |
N3—C3 | 1.472 (3) | N12—C27 | 1.361 (3) |
N4—C10 | 1.345 (3) | C19—C20 | 1.391 (3) |
N4—N5 | 1.350 (3) | C19—C24 | 1.404 (3) |
N4—C11 | 1.459 (4) | C20—C21 | 1.373 (4) |
N5—N6 | 1.316 (3) | C20—H20 | 0.94 (3) |
N6—C9 | 1.364 (3) | C21—C22 | 1.404 (4) |
C1—C2 | 1.395 (3) | C22—C23 | 1.368 (4) |
C1—C6 | 1.407 (3) | C22—H22 | 0.96 (3) |
C2—C3 | 1.375 (4) | C23—C24 | 1.397 (4) |
C2—H2 | 0.96 (3) | C23—H23 | 0.92 (3) |
C3—C4 | 1.407 (4) | C24—C25 | 1.419 (3) |
C4—C5 | 1.367 (4) | C26—C27 | 1.485 (4) |
C4—H4 | 0.96 (3) | C26—H26A | 0.95 (3) |
C5—C6 | 1.397 (4) | C26—H26B | 0.98 (3) |
C5—H5 | 0.94 (3) | C27—C28 | 1.360 (3) |
C6—C7 | 1.419 (3) | C28—H28 | 0.92 (3) |
C8—C9 | 1.486 (4) | C29—C30 | 1.511 (4) |
C8—H8A | 0.98 (3) | C29—H29A | 1.00 (3) |
C8—H8B | 0.99 (3) | C29—H29B | 1.05 (3) |
C9—C10 | 1.359 (4) | C30—C31 | 1.538 (4) |
C10—H10 | 0.93 (3) | C30—H30A | 0.98 (3) |
C11—C12 | 1.511 (4) | C30—H30B | 1.05 (3) |
C11—H11A | 1.03 (3) | C31—C32 | 1.515 (5) |
C11—H11B | 1.00 (3) | C31—H31A | 1.00 (3) |
C12—C13 | 1.527 (4) | C31—H31B | 1.07 (3) |
C12—H12A | 0.96 (3) | C32—C33 | 1.525 (5) |
C12—H12B | 1.00 (3) | C32—H32A | 1.14 (4) |
C13—C14 | 1.523 (4) | C32—H32B | 1.03 (4) |
C13—H13A | 0.99 (3) | C33—C34A | 1.526 (6) |
C13—H13B | 1.04 (3) | C33—C34B | 1.526 (6) |
C14—C15 | 1.530 (4) | C33—H33A | 1.08 (4) |
C14—H14A | 1.04 (3) | C33—H33B | 1.07 (4) |
C14—H14B | 1.03 (3) | C34A—C35A | 1.525 (5) |
C15—C16 | 1.523 (4) | C34A—H34A | 0.9900 |
C15—H15A | 1.07 (3) | C34A—H34B | 0.9900 |
C15—H15B | 1.01 (3) | C35A—C36A | 1.516 (5) |
C16—C17 | 1.524 (4) | C35A—H35A | 0.9900 |
C16—H16A | 1.05 (3) | C35A—H35B | 0.9900 |
C16—H16B | 1.03 (3) | C36A—H36A | 0.9800 |
C17—C18 | 1.514 (4) | C36A—H36B | 0.9800 |
C17—H17A | 0.99 (3) | C36A—H36C | 0.9800 |
C17—H17B | 1.02 (3) | C34B—C35B | 1.525 (5) |
C18—H18A | 1.06 (4) | C34B—H34C | 0.9900 |
C18—H18B | 1.01 (4) | C34B—H34D | 0.9900 |
C18—H18C | 0.99 (4) | C35B—C36B | 1.516 (5) |
Cl2—C25 | 1.709 (2) | C35B—H35C | 0.9900 |
O3—N9 | 1.224 (3) | C35B—H35D | 0.9900 |
O4—N9 | 1.221 (3) | C36B—H36D | 0.9800 |
N7—C25 | 1.315 (3) | C36B—H36E | 0.9800 |
N7—N8 | 1.369 (3) | C36B—H36F | 0.9800 |
C7—N1—N2 | 105.6 (2) | N11—N12—C27 | 108.8 (2) |
C1—N2—N1 | 111.3 (2) | N8—C19—C20 | 130.7 (2) |
C1—N2—C8 | 127.4 (2) | N8—C19—C24 | 107.3 (2) |
N1—N2—C8 | 120.4 (2) | C20—C19—C24 | 122.0 (2) |
O1—N3—O2 | 123.5 (2) | C21—C20—C19 | 115.2 (2) |
O1—N3—C3 | 118.0 (2) | C21—C20—H20 | 122.1 (15) |
O2—N3—C3 | 118.5 (2) | C19—C20—H20 | 122.7 (15) |
C10—N4—N5 | 110.6 (2) | C20—C21—C22 | 124.4 (2) |
C10—N4—C11 | 129.2 (2) | C20—C21—N9 | 117.7 (2) |
N5—N4—C11 | 120.2 (2) | C22—C21—N9 | 117.9 (2) |
N6—N5—N4 | 107.0 (2) | C23—C22—C21 | 119.4 (2) |
N5—N6—C9 | 108.8 (2) | C23—C22—H22 | 120.0 (17) |
N2—C1—C2 | 130.3 (2) | C21—C22—H22 | 120.6 (17) |
N2—C1—C6 | 107.2 (2) | C22—C23—C24 | 118.3 (3) |
C2—C1—C6 | 122.5 (2) | C22—C23—H23 | 119.7 (15) |
C3—C2—C1 | 114.6 (2) | C24—C23—H23 | 121.9 (15) |
C3—C2—H2 | 121.2 (15) | C23—C24—C19 | 120.7 (2) |
C1—C2—H2 | 124.2 (15) | C23—C24—C25 | 136.1 (2) |
C2—C3—C4 | 124.5 (2) | C19—C24—C25 | 103.3 (2) |
C2—C3—N3 | 117.5 (2) | N7—C25—C24 | 112.8 (2) |
C4—C3—N3 | 118.0 (2) | N7—C25—Cl2 | 120.86 (18) |
C5—C4—C3 | 119.7 (3) | C24—C25—Cl2 | 126.3 (2) |
C5—C4—H4 | 122.9 (17) | N8—C26—C27 | 113.4 (2) |
C3—C4—H4 | 117.3 (17) | N8—C26—H26A | 106.3 (17) |
C4—C5—C6 | 118.2 (3) | C27—C26—H26A | 111.8 (17) |
C4—C5—H5 | 120.1 (16) | N8—C26—H26B | 106.6 (15) |
C6—C5—H5 | 121.6 (16) | C27—C26—H26B | 110.3 (16) |
C5—C6—C1 | 120.4 (2) | H26A—C26—H26B | 108 (2) |
C5—C6—C7 | 136.4 (2) | C28—C27—N12 | 108.0 (2) |
C1—C6—C7 | 103.2 (2) | C28—C27—C26 | 129.6 (2) |
N1—C7—C6 | 112.6 (2) | N12—C27—C26 | 122.3 (2) |
N1—C7—Cl1 | 120.92 (19) | N10—C28—C27 | 105.4 (2) |
C6—C7—Cl1 | 126.4 (2) | N10—C28—H28 | 117.6 (17) |
N2—C8—C9 | 112.6 (2) | C27—C28—H28 | 136.8 (17) |
N2—C8—H8A | 108.2 (16) | N10—C29—C30 | 113.2 (2) |
C9—C8—H8A | 110.3 (16) | N10—C29—H29A | 109.1 (19) |
N2—C8—H8B | 107.8 (16) | C30—C29—H29A | 108.5 (19) |
C9—C8—H8B | 113.1 (16) | N10—C29—H29B | 103.5 (16) |
H8A—C8—H8B | 105 (2) | C30—C29—H29B | 113.0 (15) |
C10—C9—N6 | 108.3 (2) | H29A—C29—H29B | 109 (2) |
C10—C9—C8 | 130.1 (2) | C29—C30—C31 | 109.5 (3) |
N6—C9—C8 | 121.6 (2) | C29—C30—H30A | 110.9 (19) |
N4—C10—C9 | 105.3 (2) | C31—C30—H30A | 109.1 (19) |
N4—C10—H10 | 122.4 (18) | C29—C30—H30B | 110.5 (15) |
C9—C10—H10 | 132.2 (18) | C31—C30—H30B | 109.7 (16) |
N4—C11—C12 | 113.2 (2) | H30A—C30—H30B | 107 (2) |
N4—C11—H11A | 107.9 (16) | C32—C31—C30 | 114.5 (3) |
C12—C11—H11A | 107.2 (16) | C32—C31—H31A | 110 (2) |
N4—C11—H11B | 109.0 (15) | C30—C31—H31A | 108 (2) |
C12—C11—H11B | 109.6 (15) | C32—C31—H31B | 107.6 (18) |
H11A—C11—H11B | 110 (2) | C30—C31—H31B | 109.0 (17) |
C11—C12—C13 | 110.7 (3) | H31A—C31—H31B | 108 (3) |
C11—C12—H12A | 109.3 (18) | C31—C32—C33 | 113.8 (3) |
C13—C12—H12A | 110.7 (18) | C31—C32—H32A | 108.2 (18) |
C11—C12—H12B | 108.0 (16) | C33—C32—H32A | 110.7 (18) |
C13—C12—H12B | 111.0 (16) | C31—C32—H32B | 110 (2) |
H12A—C12—H12B | 107 (2) | C33—C32—H32B | 108 (2) |
C14—C13—C12 | 114.8 (3) | H32A—C32—H32B | 106 (3) |
C14—C13—H13A | 110.2 (17) | C32—C33—C34A | 120.2 (9) |
C12—C13—H13A | 105.5 (17) | C32—C33—C34B | 106.2 (10) |
C14—C13—H13B | 109.4 (16) | C32—C33—H33A | 108.2 (18) |
C12—C13—H13B | 109.6 (16) | C34A—C33—H33A | 107 (2) |
H13A—C13—H13B | 107 (2) | C34B—C33—H33A | 115 (2) |
C13—C14—C15 | 113.4 (3) | C32—C33—H33B | 111 (2) |
C13—C14—H14A | 109.8 (17) | C34A—C33—H33B | 108 (2) |
C15—C14—H14A | 106.1 (17) | C34B—C33—H33B | 115 (3) |
C13—C14—H14B | 109.1 (17) | H33A—C33—H33B | 102 (3) |
C15—C14—H14B | 110.3 (17) | C35A—C34A—C33 | 116.1 (12) |
H14A—C14—H14B | 108 (2) | C35A—C34A—H34A | 108.3 |
C16—C15—C14 | 113.4 (3) | C33—C34A—H34A | 108.3 |
C16—C15—H15A | 111.2 (16) | C35A—C34A—H34B | 108.3 |
C14—C15—H15A | 107.7 (16) | C33—C34A—H34B | 108.3 |
C16—C15—H15B | 109.6 (18) | H34A—C34A—H34B | 107.4 |
C14—C15—H15B | 109.5 (18) | C36A—C35A—C34A | 113.4 (5) |
H15A—C15—H15B | 105 (2) | C36A—C35A—H35A | 108.9 |
C15—C16—C17 | 112.8 (3) | C34A—C35A—H35A | 108.9 |
C15—C16—H16A | 108.3 (15) | C36A—C35A—H35B | 108.9 |
C17—C16—H16A | 110.2 (14) | C34A—C35A—H35B | 108.9 |
C15—C16—H16B | 111.9 (17) | H35A—C35A—H35B | 107.7 |
C17—C16—H16B | 108.5 (17) | C35A—C36A—H36A | 109.5 |
H16A—C16—H16B | 105 (2) | C35A—C36A—H36B | 109.5 |
C18—C17—C16 | 113.3 (3) | H36A—C36A—H36B | 109.5 |
C18—C17—H17A | 111.5 (17) | C35A—C36A—H36C | 109.5 |
C16—C17—H17A | 107.5 (17) | H36A—C36A—H36C | 109.5 |
C18—C17—H17B | 109.4 (18) | H36B—C36A—H36C | 109.5 |
C16—C17—H17B | 110.7 (17) | C35B—C34B—C33 | 110.8 (14) |
H17A—C17—H17B | 104 (2) | C35B—C34B—H34C | 109.5 |
C17—C18—H18A | 113 (2) | C33—C34B—H34C | 109.5 |
C17—C18—H18B | 112 (2) | C35B—C34B—H34D | 109.5 |
H18A—C18—H18B | 102 (3) | C33—C34B—H34D | 109.5 |
C17—C18—H18C | 113 (3) | H34C—C34B—H34D | 108.1 |
H18A—C18—H18C | 108 (3) | C36B—C35B—C34B | 113.3 (5) |
H18B—C18—H18C | 108 (3) | C36B—C35B—H35C | 108.9 |
C25—N7—N8 | 105.47 (19) | C34B—C35B—H35C | 108.9 |
C19—N8—N7 | 111.2 (2) | C36B—C35B—H35D | 108.9 |
C19—N8—C26 | 128.1 (2) | C34B—C35B—H35D | 108.9 |
N7—N8—C26 | 120.7 (2) | H35C—C35B—H35D | 107.7 |
O4—N9—O3 | 123.7 (2) | C35B—C36B—H36D | 109.5 |
O4—N9—C21 | 118.4 (2) | C35B—C36B—H36E | 109.5 |
O3—N9—C21 | 117.9 (2) | H36D—C36B—H36E | 109.5 |
N11—N10—C28 | 110.5 (2) | C35B—C36B—H36F | 109.5 |
N11—N10—C29 | 120.7 (2) | H36D—C36B—H36F | 109.5 |
C28—N10—C29 | 128.7 (2) | H36E—C36B—H36F | 109.5 |
N12—N11—N10 | 107.2 (2) | ||
C7—N1—N2—C1 | −1.0 (3) | C28—N10—N11—N12 | −0.2 (3) |
C7—N1—N2—C8 | −171.4 (2) | C29—N10—N11—N12 | 178.9 (2) |
C10—N4—N5—N6 | −0.2 (3) | N10—N11—N12—C27 | −0.1 (3) |
C11—N4—N5—N6 | 179.7 (2) | N7—N8—C19—C20 | 179.6 (2) |
N4—N5—N6—C9 | 0.0 (3) | C26—N8—C19—C20 | −3.2 (4) |
N1—N2—C1—C2 | −178.6 (2) | N7—N8—C19—C24 | −0.2 (3) |
C8—N2—C1—C2 | −9.0 (4) | C26—N8—C19—C24 | 177.1 (2) |
N1—N2—C1—C6 | 0.5 (3) | N8—C19—C20—C21 | 179.3 (2) |
C8—N2—C1—C6 | 170.1 (2) | C24—C19—C20—C21 | −1.0 (4) |
N2—C1—C2—C3 | 179.2 (3) | C19—C20—C21—C22 | 0.6 (4) |
C6—C1—C2—C3 | 0.2 (4) | C19—C20—C21—N9 | 179.7 (2) |
C1—C2—C3—C4 | 0.5 (4) | O4—N9—C21—C20 | 5.6 (3) |
C1—C2—C3—N3 | −178.6 (2) | O3—N9—C21—C20 | −174.5 (2) |
O1—N3—C3—C2 | 178.4 (2) | O4—N9—C21—C22 | −175.3 (2) |
O2—N3—C3—C2 | −0.9 (3) | O3—N9—C21—C22 | 4.6 (4) |
O1—N3—C3—C4 | −0.7 (3) | C20—C21—C22—C23 | 0.2 (4) |
O2—N3—C3—C4 | −180.0 (2) | N9—C21—C22—C23 | −178.9 (2) |
C2—C3—C4—C5 | −0.6 (4) | C21—C22—C23—C24 | −0.6 (4) |
N3—C3—C4—C5 | 178.4 (2) | C22—C23—C24—C19 | 0.3 (4) |
C3—C4—C5—C6 | 0.0 (4) | C22—C23—C24—C25 | 180.0 (3) |
C4—C5—C6—C1 | 0.7 (4) | N8—C19—C24—C23 | −179.6 (2) |
C4—C5—C6—C7 | −179.6 (3) | C20—C19—C24—C23 | 0.6 (4) |
N2—C1—C6—C5 | 180.0 (2) | N8—C19—C24—C25 | 0.6 (3) |
C2—C1—C6—C5 | −0.9 (4) | C20—C19—C24—C25 | −179.2 (2) |
N2—C1—C6—C7 | 0.2 (3) | N8—N7—C25—C24 | 0.7 (3) |
C2—C1—C6—C7 | 179.4 (2) | N8—N7—C25—Cl2 | −179.31 (17) |
N2—N1—C7—C6 | 1.2 (3) | C23—C24—C25—N7 | 179.4 (3) |
N2—N1—C7—Cl1 | −179.25 (18) | C19—C24—C25—N7 | −0.8 (3) |
C5—C6—C7—N1 | 179.4 (3) | C23—C24—C25—Cl2 | −0.5 (5) |
C1—C6—C7—N1 | −0.9 (3) | C19—C24—C25—Cl2 | 179.23 (19) |
C5—C6—C7—Cl1 | −0.1 (5) | C19—N8—C26—C27 | −77.4 (3) |
C1—C6—C7—Cl1 | 179.6 (2) | N7—N8—C26—C27 | 99.6 (3) |
C1—N2—C8—C9 | −73.4 (3) | N11—N12—C27—C28 | 0.3 (3) |
N1—N2—C8—C9 | 95.3 (3) | N11—N12—C27—C26 | −177.2 (2) |
N5—N6—C9—C10 | 0.2 (3) | N8—C26—C27—C28 | 111.7 (3) |
N5—N6—C9—C8 | −179.2 (2) | N8—C26—C27—N12 | −71.4 (3) |
N2—C8—C9—C10 | 106.5 (3) | N11—N10—C28—C27 | 0.3 (3) |
N2—C8—C9—N6 | −74.2 (3) | C29—N10—C28—C27 | −178.6 (2) |
N5—N4—C10—C9 | 0.3 (3) | N12—C27—C28—N10 | −0.4 (3) |
C11—N4—C10—C9 | −179.5 (3) | C26—C27—C28—N10 | 176.8 (2) |
N6—C9—C10—N4 | −0.3 (3) | N11—N10—C29—C30 | 95.7 (3) |
C8—C9—C10—N4 | 179.1 (3) | C28—N10—C29—C30 | −85.4 (3) |
C10—N4—C11—C12 | −109.4 (3) | N10—C29—C30—C31 | 176.9 (3) |
N5—N4—C11—C12 | 70.8 (3) | C29—C30—C31—C32 | 173.6 (3) |
N4—C11—C12—C13 | −178.0 (2) | C30—C31—C32—C33 | −63.7 (4) |
C11—C12—C13—C14 | 178.8 (2) | C31—C32—C33—C34A | −159 (2) |
C12—C13—C14—C15 | −54.8 (4) | C31—C32—C33—C34B | −160.8 (19) |
C13—C14—C15—C16 | −165.4 (3) | C32—C33—C34A—C35A | −178 (2) |
C14—C15—C16—C17 | −175.9 (3) | C33—C34A—C35A—C36A | −174 (2) |
C15—C16—C17—C18 | −176.2 (3) | C32—C33—C34B—C35B | 177 (3) |
C25—N7—N8—C19 | −0.3 (3) | C33—C34B—C35B—C36B | −178 (3) |
C25—N7—N8—C26 | −177.8 (2) |
Cg1, Cg2 and Cg3 are the centroids of the N7/N8/C19/C24/C25, N10/N11/N12/C27/C28 and C19–C24 rings, respectively |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O2i | 0.98 (3) | 2.62 (3) | 3.348 (3) | 132 (2) |
C10—H10···N6ii | 0.93 (3) | 2.57 (3) | 3.377 (3) | 145 (2) |
C26—H26A···O4iii | 0.95 (3) | 2.54 (3) | 3.240 (3) | 131 (2) |
C26—H26B···Cl2iv | 0.98 (3) | 2.82 (3) | 3.682 (3) | 147 (2) |
C28—H28···N12iv | 0.92 (3) | 2.45 (3) | 3.298 (3) | 152 (2) |
C29—H29B···N11iv | 1.05 (3) | 2.63 (3) | 3.594 (4) | 153 (2) |
C29—H29B···N12iv | 1.05 (3) | 2.65 (3) | 3.476 (3) | 135 (2) |
Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) x, −y−1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y+1/2, z−1/2. |
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.
References
Boulhaoua, M., Abdelahi, M. M., Benchidmi, M., Essassi, E. M. & Mague, J. T. (2016). IUCrData, 1, x160485. Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2009). TWINABS. University of Göttingen, Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.