3-[(3,5-Dimethyl-1H-pyrazol-1-yl)meth­yl]-4-(4-methyl­phen­yl)-4,5-di­hydro-1H-1,2,4-triazole-5-thione

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Marzouk, A.A.; Hawaiz, F.E.; Abdel-Rahman, H.M.

doi:10.1107/S2414314617001535

organic compounds

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ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170153

https://doi.org/10.1107/S2414314617001535

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3-[(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-(4-methylphenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Adel A. Marzouk,^e Farouq E. Hawaiz ^f ^* and Hamdy M. Abdel-Rahman ^g

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, 71515 Assiut, Egypt, ^fChemistry Department, College of Education, Salahaddin University-Hawler, Erbil, Kurdistan Region, Iraq, and ^gFaculty of Pharmacy, Medicinal Chemistry Department, Assiut University, Assiut 71526, Egypt
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 26 January 2017; accepted 30 January 2017; online 3 February 2017)

With the pyrazolyl and p-tolyl groups lying to one side of the plane through the linking 1,2,4-triazole-5-thione residue [forming dihedral angles of 87.05 (8) and 81.41 (7)°, respectively], the title molecule, C₁₅H₁₇N₅S, adopts a `pincer' conformation stabilized in part by two intramolecular C—H⋯π(ring) interactions. A three-dimensional network structure is generated by a combination of intermolecular N—H⋯N and C—H⋯S hydrogen bonds, as well as C—H⋯π(ring) interactions.

Keywords: crystal structure; hydrogen bonding; pyrazole; triazole; C—H⋯π(ring) interactions; hydrogen bonds.

CCDC reference: 1530082

Structure description

Pyrazoles and their derivatives are an important class of heterocyclic compounds due to their broad spectrum of biological properties. They exhibit anti-bacterial, anti-depressant (Liu et al., 2008 ; Yhya et al., 2012 ), anti-oxidant (Abdel-Aziz et al. 2009 ), anti-cancer (Grosse et al., 2014 ) and anti-viral activities (Hamdy & El-Senousy, 2013 ) in addition to their anti-inflammatory and anti-microbial activities. Moreover, pyrazoles containing 4-substituted-1,2,4-triazole-3-thiones have been reported to possess anti-inflammatory activities (El-Moghazy et al., 2012 ). As part of our research in this area, we report herein the synthesis and crystal structure of the title compound.

The title molecule adopts a `pincer' conformation which is at least partly determined by two intramolecular C—H⋯π(ring) interactions (Table 1 and Fig. 1). The dihedral angle between the C3–C8 and N1–N3/C1/C2 rings is 81.41 (7)° while that between the latter ring and the N4/N5,C11–C13 ring is 87.05 (8)°. Pairwise N3—H3⋯N5^v hydrogen bonds (Table 1) form dimers which are linked into a three-dimensional network by a combination of three sets of C—H⋯S hydrogen bonds and a set of C—H⋯π(ring) interactions (Table 1 and Figs. 2 and 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1–N3/C1/C2, N4/N5/C11–C13 and C3–C8 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg2	0.95	2.81	3.2544 (14)	110
C14—H14A⋯Cg3	0.98	2.79	3.6130 (17)	143
N3—H3N⋯N5ⁱ	0.878 (18)	1.978 (18)	2.8334 (17)	164.5 (16)
C15—H15C⋯N2ⁱⁱ	0.98	2.59	3.550 (2)	168
C9—H9B⋯Cg1ⁱⁱ	0.98	2.88	3.637 (2)	135
C5—H5⋯S1ⁱⁱⁱ	0.95	2.93	3.824 (2)	157
C10—H10A⋯S1^iv	0.99	2.93	3.747 (1)	140
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x-1, y, z; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
The title molecule with labelling scheme and 50% probability ellipsoids. The intramolecular C—H⋯π(ring) interactions are shown as dotted lines.

Figure 2
Detail of the intermolecular N—H⋯N (blue dotted lines) and C—H⋯S (black dotted lines) hydrogen bonds and the intermolecular C—H⋯π(ring) (orange dotted lines) interactions. [Symmetry codes: (i) −1 + x, y, z; (ii) − $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z; (iii) $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z; (iv) $[{3\over 2}]$ − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z.]

Figure 3
Packing viewed along the a axis. Intermolecular N—H⋯N and C—H⋯S hydrogen bonds are shown, respectively, as blue and black dotted lines.

Synthesis and crystallization

A solution of 2-(2-(3,5-dimethyl-1H-pyrazol-1-yl)acetyl)-N-p-tolylhydrazinecarbothioamide (1.27 g; 4 mmol) in ethanol (50 ml) was added dropwise to 2 N sodium hydroxide solution (20 ml). The reaction mixture was then refluxed for 2 h, cooled, filtered and the filtrate was acidified with 2 N hydrochloric acid solution. The separated solid was collected, washed with water and crystallized from ethanol solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₇N₅S
M_r	299.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	7.9322 (2), 15.2415 (4), 13.6694 (4)
β (°)	106.316 (1)
V (Å³)	1586.06 (7)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.81
Crystal size (mm)	0.15 × 0.15 × 0.07

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.82, 0.89
No. of measured, independent and observed [I > 2σ(I)] reflections	11791, 3070, 2812
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.05
No. of reflections	3070
No. of parameters	191
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1530082

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617001535/tk4029sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001535/tk4029Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617001535/tk4029Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: 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).

3-[(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-(4-methylphenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione top

Crystal data top

C₁₅H₁₇N₅S	F(000) = 632
M_r = 299.39	D_x = 1.254 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 7.9322 (2) Å	Cell parameters from 9878 reflections
b = 15.2415 (4) Å	θ = 2.9–72.4°
c = 13.6694 (4) Å	µ = 1.81 mm⁻¹
β = 106.316 (1)°	T = 150 K
V = 1586.06 (7) Å³	Thick plate, colourless
Z = 4	0.15 × 0.15 × 0.07 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3070 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2812 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.4°, θ_min = 4.5°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −18→18
T_min = 0.82, T_max = 0.89	l = −16→16
11791 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0454P)² + 0.6677P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.033	(Δ/σ)_max < 0.001
wR(F²) = 0.091	Δρ_max = 0.24 e Å⁻³
S = 1.05	Δρ_min = −0.21 e Å⁻³
3070 reflections	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
191 parameters	Extinction coefficient: 0.0040 (3)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.92398 (17)	0.37412 (8)	0.35362 (10)	0.0212 (2)
C2	1.00943 (17)	0.35248 (9)	0.52192 (10)	0.0212 (2)
C3	0.77405 (17)	0.25167 (9)	0.41923 (9)	0.0204 (3)
C4	0.82341 (19)	0.16998 (9)	0.39224 (11)	0.0268 (3)
H4	0.9348	0.1617	0.3805	0.032*
C5	0.7066 (2)	0.10048 (10)	0.38268 (12)	0.0341 (4)
H5	0.7370	0.0442	0.3631	0.041*
C6	0.5455 (2)	0.11329 (11)	0.40169 (11)	0.0341 (4)
H6	0.4673	0.0651	0.3957	0.041*
C7	0.49608 (19)	0.19490 (11)	0.42931 (10)	0.0290 (3)
C8	0.61277 (17)	0.26505 (9)	0.43697 (10)	0.0230 (3)
H8	0.5812	0.3219	0.4544	0.028*
C9	0.3242 (2)	0.20843 (14)	0.45340 (13)	0.0435 (4)
H9A	0.2501	0.1564	0.4327	0.065*
H9B	0.2644	0.2598	0.4163	0.065*
H9C	0.3461	0.2178	0.5268	0.065*
C10	1.01710 (18)	0.31858 (10)	0.62551 (10)	0.0257 (3)
H10A	1.0425	0.2549	0.6284	0.031*
H10B	1.1139	0.3481	0.6768	0.031*
C11	0.74452 (19)	0.27428 (9)	0.67525 (10)	0.0245 (3)
C12	0.6022 (2)	0.32088 (10)	0.68573 (11)	0.0273 (3)
H12	0.5029	0.2982	0.7032	0.033*
C13	0.63305 (19)	0.40877 (9)	0.66543 (11)	0.0263 (3)
C14	0.7851 (2)	0.17859 (10)	0.68567 (12)	0.0327 (3)
H14A	0.7884	0.1549	0.6196	0.049*
H14B	0.6940	0.1482	0.7086	0.049*
H14C	0.8995	0.1698	0.7357	0.049*
C15	0.5202 (2)	0.48732 (11)	0.66467 (15)	0.0405 (4)
H15A	0.5736	0.5388	0.6424	0.061*
H15B	0.5095	0.4975	0.7335	0.061*
H15C	0.4034	0.4772	0.6177	0.061*
N1	0.89554 (14)	0.32359 (7)	0.43150 (8)	0.0202 (2)
N2	1.10763 (15)	0.41591 (8)	0.50617 (9)	0.0250 (3)
N3	1.05596 (15)	0.42747 (8)	0.40224 (9)	0.0238 (3)
H3N	1.093 (2)	0.4738 (12)	0.3762 (13)	0.029*
N4	0.85295 (15)	0.33364 (7)	0.65030 (8)	0.0223 (2)
N5	0.78636 (15)	0.41691 (7)	0.64379 (9)	0.0242 (3)
S1	0.81896 (4)	0.36931 (2)	0.22924 (2)	0.02550 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0196 (4)	0.0185 (5)	0.0261 (5)	0.0009 (3)	0.0076 (4)	−0.0015 (3)
C2	0.0196 (4)	0.0185 (5)	0.0261 (5)	0.0009 (3)	0.0076 (4)	−0.0015 (3)
C3	0.0216 (6)	0.0199 (6)	0.0190 (6)	−0.0040 (5)	0.0045 (5)	0.0010 (5)
C4	0.0271 (7)	0.0236 (7)	0.0307 (7)	−0.0008 (5)	0.0099 (6)	−0.0023 (6)
C5	0.0444 (9)	0.0219 (7)	0.0356 (8)	−0.0068 (6)	0.0106 (7)	−0.0046 (6)
C6	0.0377 (8)	0.0338 (8)	0.0283 (7)	−0.0171 (7)	0.0052 (6)	0.0003 (6)
C7	0.0227 (7)	0.0417 (9)	0.0206 (6)	−0.0085 (6)	0.0031 (5)	0.0032 (6)
C8	0.0209 (6)	0.0272 (7)	0.0200 (6)	−0.0003 (5)	0.0042 (5)	0.0013 (5)
C9	0.0254 (8)	0.0717 (13)	0.0345 (8)	−0.0139 (8)	0.0098 (6)	−0.0007 (8)
C10	0.0222 (7)	0.0287 (7)	0.0245 (7)	0.0012 (5)	0.0037 (5)	0.0025 (5)
C11	0.0310 (7)	0.0229 (7)	0.0181 (6)	−0.0058 (5)	0.0046 (5)	0.0018 (5)
C12	0.0311 (7)	0.0281 (8)	0.0249 (7)	−0.0085 (6)	0.0114 (6)	−0.0027 (6)
C13	0.0263 (7)	0.0256 (7)	0.0270 (7)	−0.0052 (5)	0.0077 (6)	−0.0060 (6)
C14	0.0397 (9)	0.0235 (8)	0.0328 (8)	−0.0026 (6)	0.0069 (7)	0.0069 (6)
C15	0.0316 (8)	0.0315 (9)	0.0593 (11)	−0.0026 (6)	0.0141 (8)	−0.0134 (8)
N1	0.0187 (5)	0.0188 (6)	0.0232 (5)	−0.0019 (4)	0.0062 (4)	−0.0005 (4)
N2	0.0227 (6)	0.0247 (6)	0.0273 (6)	−0.0029 (4)	0.0062 (5)	−0.0020 (5)
N3	0.0254 (6)	0.0202 (6)	0.0272 (6)	−0.0047 (4)	0.0094 (5)	−0.0004 (5)
N4	0.0237 (6)	0.0209 (6)	0.0213 (5)	−0.0012 (4)	0.0047 (4)	0.0018 (4)
N5	0.0253 (6)	0.0198 (6)	0.0267 (6)	−0.0026 (4)	0.0059 (5)	−0.0008 (4)
S1	0.0306 (2)	0.0232 (2)	0.02287 (19)	−0.00195 (12)	0.00779 (14)	0.00007 (12)

Geometric parameters (Å, º) top

C1—N3	1.3446 (17)	C9—H9C	0.9800
C1—N1	1.3830 (17)	C10—N4	1.4528 (18)
C1—S1	1.6716 (14)	C10—H10A	0.9900
C2—N2	1.2969 (18)	C10—H10B	0.9900
C2—N1	1.3821 (17)	C11—N4	1.3562 (17)
C2—C10	1.4925 (18)	C11—C12	1.375 (2)
C3—C8	1.3825 (19)	C11—C14	1.492 (2)
C3—C4	1.3860 (19)	C12—C13	1.403 (2)
C3—N1	1.4378 (16)	C12—H12	0.9500
C4—C5	1.389 (2)	C13—N5	1.3356 (19)
C4—H4	0.9500	C13—C15	1.493 (2)
C5—C6	1.387 (2)	C14—H14A	0.9800
C5—H5	0.9500	C14—H14B	0.9800
C6—C7	1.388 (2)	C14—H14C	0.9800
C6—H6	0.9500	C15—H15A	0.9800
C7—C8	1.399 (2)	C15—H15B	0.9800
C7—C9	1.504 (2)	C15—H15C	0.9800
C8—H8	0.9500	N2—N3	1.3749 (16)
C9—H9A	0.9800	N3—H3N	0.877 (18)
C9—H9B	0.9800	N4—N5	1.3680 (16)

N3—C1—N1	103.24 (11)	C2—C10—H10B	109.3
N3—C1—S1	128.72 (11)	H10A—C10—H10B	108.0
N1—C1—S1	128.04 (10)	N4—C11—C12	106.20 (12)
N2—C2—N1	111.18 (12)	N4—C11—C14	122.77 (13)
N2—C2—C10	123.31 (12)	C12—C11—C14	131.03 (13)
N1—C2—C10	125.47 (12)	C11—C12—C13	106.16 (12)
C8—C3—C4	121.58 (13)	C11—C12—H12	126.9
C8—C3—N1	119.34 (12)	C13—C12—H12	126.9
C4—C3—N1	119.06 (12)	N5—C13—C12	110.66 (13)
C3—C4—C5	118.64 (14)	N5—C13—C15	120.36 (13)
C3—C4—H4	120.7	C12—C13—C15	128.98 (14)
C5—C4—H4	120.7	C11—C14—H14A	109.5
C6—C5—C4	120.01 (15)	C11—C14—H14B	109.5
C6—C5—H5	120.0	H14A—C14—H14B	109.5
C4—C5—H5	120.0	C11—C14—H14C	109.5
C5—C6—C7	121.50 (14)	H14A—C14—H14C	109.5
C5—C6—H6	119.3	H14B—C14—H14C	109.5
C7—C6—H6	119.3	C13—C15—H15A	109.5
C6—C7—C8	118.28 (13)	C13—C15—H15B	109.5
C6—C7—C9	121.68 (14)	H15A—C15—H15B	109.5
C8—C7—C9	120.03 (15)	C13—C15—H15C	109.5
C3—C8—C7	119.98 (13)	H15A—C15—H15C	109.5
C3—C8—H8	120.0	H15B—C15—H15C	109.5
C7—C8—H8	120.0	C2—N1—C1	107.70 (11)
C7—C9—H9A	109.5	C2—N1—C3	126.55 (11)
C7—C9—H9B	109.5	C1—N1—C3	125.71 (11)
H9A—C9—H9B	109.5	C2—N2—N3	104.38 (11)
C7—C9—H9C	109.5	C1—N3—N2	113.45 (11)
H9A—C9—H9C	109.5	C1—N3—H3N	126.1 (11)
H9B—C9—H9C	109.5	N2—N3—H3N	119.0 (11)
N4—C10—C2	111.49 (11)	C11—N4—N5	112.00 (11)
N4—C10—H10A	109.3	C11—N4—C10	128.80 (12)
C2—C10—H10A	109.3	N5—N4—C10	119.10 (11)
N4—C10—H10B	109.3	C13—N5—N4	104.98 (11)

C8—C3—C4—C5	0.2 (2)	N3—C1—N1—C3	−175.76 (12)
N1—C3—C4—C5	178.65 (12)	S1—C1—N1—C3	4.15 (19)
C3—C4—C5—C6	−1.1 (2)	C8—C3—N1—C2	82.53 (16)
C4—C5—C6—C7	0.7 (2)	C4—C3—N1—C2	−95.92 (16)
C5—C6—C7—C8	0.5 (2)	C8—C3—N1—C1	−100.26 (15)
C5—C6—C7—C9	−177.92 (14)	C4—C3—N1—C1	81.29 (16)
C4—C3—C8—C7	1.0 (2)	N1—C2—N2—N3	−0.52 (15)
N1—C3—C8—C7	−177.44 (11)	C10—C2—N2—N3	−178.55 (12)
C6—C7—C8—C3	−1.3 (2)	N1—C1—N3—N2	−2.35 (15)
C9—C7—C8—C3	177.12 (13)	S1—C1—N3—N2	177.75 (10)
N2—C2—C10—N4	115.87 (14)	C2—N2—N3—C1	1.86 (15)
N1—C2—C10—N4	−61.87 (17)	C12—C11—N4—N5	−0.22 (15)
N4—C11—C12—C13	0.25 (15)	C14—C11—N4—N5	179.05 (12)
C14—C11—C12—C13	−178.93 (14)	C12—C11—N4—C10	−176.50 (12)
C11—C12—C13—N5	−0.21 (16)	C14—C11—N4—C10	2.8 (2)
C11—C12—C13—C15	179.17 (15)	C2—C10—N4—C11	121.63 (14)
N2—C2—N1—C1	−0.89 (15)	C2—C10—N4—N5	−54.42 (16)
C10—C2—N1—C1	177.09 (12)	C12—C13—N5—N4	0.08 (15)
N2—C2—N1—C3	176.74 (12)	C15—C13—N5—N4	−179.37 (13)
C10—C2—N1—C3	−5.3 (2)	C11—N4—N5—C13	0.09 (14)
N3—C1—N1—C2	1.89 (14)	C10—N4—N5—C13	176.77 (11)
S1—C1—N1—C2	−178.20 (10)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N1–N3/C1/C2, N4/N5/C11–C13 and C3–C8 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg2	0.95	2.81	3.2544 (14)	110
C14—H14A···Cg3	0.98	2.79	3.6130 (17)	143
N3—H3N···N5ⁱ	0.878 (18)	1.978 (18)	2.8334 (17)	164.5 (16)
C15—H15C···N2ⁱⁱ	0.98	2.59	3.550 (2)	168
C9—H9B···Cg1ⁱⁱ	0.98	2.88	3.637 (2)	135
C5—H5···S1ⁱⁱⁱ	0.95	2.93	3.824 (2)	157
C10—H10A···S1^iv	0.99	2.93	3.747 (1)	140

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x+1/2, −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.

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