Crystal structure and Hirshfeld surface analysis of 3-[(1E)-(4-{4-[(E)-(3-hy­droxy­benzyl­idene)amino]­phen­oxy}phenyl­imino)­meth­yl]phenol

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Hawaiz, F.E.; Elgarhy, S.M.I.; Al-Taifi, E.A.

doi:10.1107/S205698902100181X

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ISSN: 2056-9890

Volume 77| Part 3| March 2021| Pages 266-269

https://doi.org/10.1107/S205698902100181X

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Crystal structure and Hirshfeld surface analysis of 3-[(1E)-(4-{4-[(E)-(3-hydroxybenzylidene)amino]phenoxy}phenylimino)methyl]phenol

Shaaban K. Mohamed,^a,^b Joel T. Mague,^c Mehmet Akkurt,^d Farouq E. Hawaiz,^e Sahar M. I. Elgarhy ^f and Elham A. Al-Taifi ^g ^*

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, College of Education, Salahaddin University-Hawler, Erbil, Kurdistan Region, Iraq, ^fFaculty of Science, Department of Biochemistry, Beni Suef University, Beni Suef, Egypt, and ^gDepartment of Chemistry, Faculty of Science, Sana'a University, Sana'a, Yemen
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by A. V. Yatsenko, Moscow State University, Russia (Received 2 February 2021; accepted 14 February 2021; online 19 February 2021)

In the crystal, the molecule of the title compound, C₂₆H₂₀N₂O₃, has crystallographically imposed twofold rotation symmetry. The crystal packing consists of layers parallel to the ab plane formed by O—H⋯N and C—H⋯O hydrogen bonds. Between the layers, C—H⋯π interactions are observed.

Keywords: crystal structure; hydrogen bond; phenol; aromatic ether; phenoxy; azomethines; Hirshfeld surface analysis.

CCDC reference: 2062957

1. Chemical context

Several Schiff bases have been reported for their significant biological activities such as antitumor (Mansouri et al., 2013 ), anti-inflammatory (Shukla & Mishra, 2019 ), antibacterial (Van Zee & Coates, 2015 ) or antimicrobial (Pagadala et al., 2015 ). Schiff bases are also used as versatile components in nucleophilic addition with organometallic reagents and in cycloaddition reactions (Mohan et al., 2012 ). These findings prompted us to investigate the crystal structure of the title compound.

2. Structural commentary

The molecule of the title compound has crystallographically imposed twofold rotation symmetry (Fig. 1). The dihedral angle between the two unique benzene rings is 40.68 (6)° while the dihedral angle between the two central benzene rings is 77.71 (6)°. Bond lengths are typical for this kind of compounds.

Figure 1
The title molecule with labeling scheme and 50% probability ellipsoids [symmetry code: (i) −x + 1, y, −z + $[{1\over 2}]$ ].

3. Supramolecular features

In the crystal, O2—H2A⋯N1 and C5—H5⋯O2 hydrogen bonds link the molecules into layers parallel to the ab plane (Table 1, Fig. 2). The layers are hold together by C—H⋯π contacts (Table 1, Fig. 3) and by other van der Waals interactions (Table 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1ⁱ	0.972 (19)	1.828 (19)	2.7615 (12)	160.1 (16)
C5—H5⋯O2ⁱⁱ	0.973 (13)	2.431 (14)	3.1121 (14)	126.7 (10)
C12—H11⋯Cg1ⁱⁱ	1.004 (14)	2.986 (15)	3.9882 (12)	178.7 (19)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Short intermolecular contacts (Å) in the title structure

Contact	Distance	Symmetry operation
H12⋯O1	2.763 (14)	1 − x, 2 − y, 1 − z
H6⋯H11	2.53 (2)	x, 2 − y, − $[{1\over 2}]$ + z
C3⋯C6	3.5155 (15)	x, −1 + y, z
C6⋯H11	2.892 (15)	x, 1 − y, − $[{1\over 2}]$ + z
C11⋯C11	3.319 (2)	$[{1\over 2}]$ − x, $[{1\over 2}]$ − y, 1 − z
H11⋯H2	2.40 (3)	1 − x, 1 − y, 1 − z

Figure 2
The layer structure viewed along the c-axis direction. The intermolecular O—H⋯N and C—H⋯O hydrogen bonds are shown as red and black dashed lines, respectively.

Figure 3
Side view of two layers seen along the b-axis direction. Hydrogen bonds and C—H⋯π interactions are depicted by dashed lines.

4. Hirshfeld surface analysis

Hirshfeld surface analysis, together with two-dimensional fingerprint plots, is an important tool for visualizing and analyzing intermolecular contacts in molecular crystals. The corresponding surfaces and fingerprint plots were prepared by CrystalExplorer (Turner et al., 2017 ). Fig. 4 shows the d_norm map for the title molecule, with red spots indicating the positions of H⋯N contacts arising from the O—H⋯N hydrogen bonds.

Figure 4
A view of the three-dimensional Hirshfeld surface for the title compound, plotted over d_norm in the range −1.1242 to 1.4437 a.u.

Fig. 5 shows the two-dimensional fingerprint plots, which give the contributions of intermolecular contacts to the Hirshfeld surface. The most important contribution to the Hirshfeld surface (41.6%) is from H⋯H contacts. C⋯H/H⋯C and O⋯H/H⋯O interactions follow with 28.1% and 13.8% contributions, respectively. Other minor contributors are C⋯C (5.3%), N⋯H/H⋯N (4.8%), O⋯C/C⋯O (3.8%) and N⋯C/C⋯N (2.6%) contacts.

Figure 5
A view of the two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C and (d) O⋯H/H⋯O interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

Five related compounds with a 4-[(E)-benzylideneamino]phenol skeleton are: (E)-2-{[(2-aminophenyl)imino]methyl}-5-(benzyloxy)phenol (NIBRIC; Ghichi et al., 2018 ), (Z)-3-(benzyloxy)-6-{[(5-chloro-2-hydroxyphenyl)amino]methylidene}cyclohexa-2,4-dien-1-one (NIBROI; Ghichi et al., 2018), 2-{(E)-[(2-methyl-3-nitrophenyl)imino]methyl}-4-nitrophenol (AFOPUI; Tanak et al., 2013 ), 2-[(E)-(2-chlorophenyl)iminomethyl]-6-methylphenol (SABKOX; Zhu et al., 2010 ) and 2-{[(2,4-dimethylphenyl)imino]methyl}-6-methylphenol (MUCDIY; Tanak et al., 2009 ).

In the crystal of NIBRIC, strong N—H⋯O hydrogen bonds form zigzag chains of molecules along the b-axis direction. Weaker C—H⋯π and offset π–π stacking interactions also contribute to the packing. For NIBROI, pairs of strong O—H⋯O hydrogen bonds form centrosymmetric dimers that enclose R₂²(18) rings. These combine with weaker C—H⋯Cl hydrogen bonds, which also generate centrosymmetric dimers, but with R₂²(14) motifs. Inversion-related C—H⋯π contacts lead to the formation of sheets of molecules parallel to (120), which are stacked approximately along the b-axis direction. In the crystal of AFOPUI, molecules are linked by C—H⋯O interactions, forming two-dimensional sheets parallel to the bc plane. In the structure of SABKOX, the hydroxy H atom is involved in a strong intramolecular O—H⋯N hydrogen bond, generating a S(6) ring. The molecular structure of MUCDIY is stabilized by an intramolecular O—H⋯N hydrogen bond, which generates a six membered ring.

6. Synthesis and crystallization

Condensation of 1 mmol of 4,4′-oxydibenzaldehyde (226 mg) with 2 mmol of 3-aminophenol (218 mg) in ethanol under reflux for 4 h afforded the crude product of the title compound. The product was crystallized from ethanol by slow evaporation to obtain good quality crystals for X-ray diffraction. Yield 82%.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms were located in a difference-Fourier map and refined freely.

Table 3
Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₂O₃
M_r	408.44
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	26.8396 (6), 5.1174 (1), 17.2574 (4)
β (°)	121.764 (1)
V (Å³)	2015.27 (8)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.72
Crystal size (mm)	0.25 × 0.06 × 0.06

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.90, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	15449, 1880, 1767
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.086, 1.05
No. of reflections	1880
No. of parameters	182
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 2062957

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S205698902100181X/yk2146sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902100181X/yk2146Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698902100181X/yk2146Isup3.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: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-[(1E)-(4-{4-[(E)-(3-Hydroxybenzylidene)amino]phenoxy}phenylimino)methyl]phenol top

Crystal data top

C₂₆H₂₀N₂O₃	F(000) = 856
M_r = 408.44	D_x = 1.346 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
a = 26.8396 (6) Å	Cell parameters from 9934 reflections
b = 5.1174 (1) Å	θ = 3.9–69.8°
c = 17.2574 (4) Å	µ = 0.72 mm⁻¹
β = 121.764 (1)°	T = 150 K
V = 2015.27 (8) Å³	Column, colourless
Z = 4	0.25 × 0.06 × 0.06 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	1880 independent reflections
Radiation source: INCOATEC IµS micro–focus source	1767 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.4167 pixels mm^-1	θ_max = 69.8°, θ_min = 3.9°
ω scans	h = −32→32
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −6→6
T_min = 0.90, T_max = 0.96	l = −20→20
15449 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	All H-atom parameters refined
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.043P)² + 1.3008P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1880 reflections	Δρ_max = 0.19 e Å⁻³
182 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL 2016/6 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (2)

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.

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.

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

	x	y	z	U_iso*/U_eq
O1	0.500000	1.3874 (2)	0.250000	0.0267 (3)
O2	0.21618 (3)	0.09976 (18)	0.33558 (6)	0.0336 (2)
H2A	0.1966 (8)	0.182 (4)	0.2759 (13)	0.066 (5)*
N1	0.36195 (4)	0.78690 (18)	0.33726 (6)	0.0233 (2)
C1	0.46708 (5)	1.2402 (2)	0.27573 (7)	0.0228 (3)
C2	0.49250 (5)	1.0380 (2)	0.33777 (8)	0.0288 (3)
H2	0.5331 (6)	0.994 (3)	0.3625 (9)	0.035 (3)*
C3	0.45903 (5)	0.8917 (2)	0.36148 (8)	0.0276 (3)
H3	0.4769 (6)	0.743 (3)	0.4038 (9)	0.033 (3)*
C4	0.39966 (4)	0.9482 (2)	0.32294 (7)	0.0220 (3)
C5	0.37512 (5)	1.1545 (2)	0.26182 (7)	0.0244 (3)
H5	0.3337 (6)	1.192 (3)	0.2353 (9)	0.031 (3)*
C6	0.40866 (5)	1.3034 (2)	0.23883 (7)	0.0242 (3)
H6	0.3914 (5)	1.445 (3)	0.1965 (9)	0.030 (3)*
C7	0.38127 (5)	0.6916 (2)	0.41641 (7)	0.0254 (3)
H7	0.4211 (6)	0.744 (3)	0.4696 (10)	0.035 (4)*
C8	0.35036 (5)	0.4960 (2)	0.43754 (7)	0.0238 (3)
C9	0.29481 (5)	0.4001 (2)	0.37197 (7)	0.0242 (3)
H9	0.2735 (5)	0.460 (3)	0.3094 (9)	0.026 (3)*
C10	0.26950 (5)	0.2038 (2)	0.39519 (7)	0.0242 (3)
H10	0.2803 (6)	−0.038 (3)	0.4990 (9)	0.030 (3)*
C11	0.29889 (5)	0.1028 (2)	0.48379 (8)	0.0262 (3)
H11	0.3729 (6)	0.127 (3)	0.6118 (10)	0.034 (3)*
C12	0.35320 (5)	0.2004 (2)	0.54851 (8)	0.0278 (3)
H12	0.4190 (6)	0.465 (3)	0.5730 (9)	0.030 (3)*
C13	0.37916 (5)	0.3963 (2)	0.52590 (8)	0.0268 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0298 (6)	0.0206 (5)	0.0400 (6)	0.000	0.0254 (5)	0.000
O2	0.0266 (4)	0.0395 (5)	0.0285 (5)	−0.0111 (4)	0.0103 (4)	−0.0010 (4)
N1	0.0218 (5)	0.0235 (5)	0.0265 (5)	0.0009 (4)	0.0141 (4)	0.0018 (4)
C1	0.0256 (5)	0.0208 (5)	0.0278 (6)	−0.0023 (4)	0.0181 (5)	−0.0032 (4)
C2	0.0204 (5)	0.0313 (6)	0.0344 (6)	0.0025 (5)	0.0142 (5)	0.0046 (5)
C3	0.0240 (6)	0.0273 (6)	0.0304 (6)	0.0030 (5)	0.0136 (5)	0.0066 (5)
C4	0.0224 (5)	0.0226 (5)	0.0235 (5)	−0.0011 (4)	0.0138 (4)	−0.0019 (4)
C5	0.0221 (5)	0.0262 (6)	0.0275 (6)	0.0037 (4)	0.0148 (5)	0.0013 (4)
C6	0.0276 (6)	0.0215 (5)	0.0277 (6)	0.0042 (4)	0.0175 (5)	0.0020 (4)
C7	0.0237 (5)	0.0276 (6)	0.0247 (6)	−0.0018 (4)	0.0125 (5)	−0.0010 (4)
C8	0.0235 (5)	0.0251 (6)	0.0249 (6)	−0.0002 (4)	0.0142 (5)	−0.0010 (4)
C9	0.0238 (5)	0.0275 (6)	0.0219 (6)	0.0008 (4)	0.0124 (5)	0.0012 (4)
C10	0.0209 (5)	0.0267 (6)	0.0257 (6)	−0.0014 (4)	0.0128 (5)	−0.0035 (4)
C11	0.0274 (6)	0.0254 (6)	0.0299 (6)	−0.0001 (4)	0.0179 (5)	0.0021 (4)
C12	0.0271 (6)	0.0317 (6)	0.0249 (6)	0.0033 (5)	0.0140 (5)	0.0046 (5)
C13	0.0224 (5)	0.0325 (6)	0.0237 (6)	−0.0011 (5)	0.0109 (5)	−0.0003 (5)

Geometric parameters (Å, º) top

O1—C1ⁱ	1.3992 (12)	C5—H5	0.973 (13)
O1—C1	1.3993 (12)	C6—H6	0.959 (14)
O2—C10	1.3563 (13)	C7—C8	1.4634 (15)
O2—H2A	0.972 (19)	C7—H7	1.012 (14)
N1—C7	1.2755 (14)	C8—C13	1.3935 (15)
N1—C4	1.4250 (13)	C8—C9	1.4028 (15)
C1—C2	1.3831 (16)	C9—C10	1.3848 (16)
C1—C6	1.3849 (15)	C9—H9	0.967 (13)
C2—C3	1.3865 (16)	C10—C11	1.3991 (16)
C2—H2	0.965 (14)	C11—C12	1.3812 (16)
C3—C4	1.3961 (15)	C11—H10	0.988 (14)
C3—H3	0.988 (15)	C12—C13	1.3888 (16)
C4—C5	1.3891 (16)	C12—H11	1.004 (14)
C5—C6	1.3871 (15)	C13—H12	1.007 (13)

C1ⁱ—O1—C1	114.87 (11)	N1—C7—C8	124.35 (10)
C10—O2—H2A	113.5 (11)	N1—C7—H7	120.7 (8)
C7—N1—C4	118.81 (9)	C8—C7—H7	114.9 (8)
C2—C1—C6	120.56 (10)	C13—C8—C9	119.77 (10)
C2—C1—O1	120.77 (9)	C13—C8—C7	117.53 (10)
C6—C1—O1	118.66 (9)	C9—C8—C7	122.65 (10)
C1—C2—C3	120.01 (10)	C10—C9—C8	119.69 (10)
C1—C2—H2	119.8 (9)	C10—C9—H9	117.3 (8)
C3—C2—H2	120.1 (9)	C8—C9—H9	122.9 (8)
C2—C3—C4	120.12 (10)	O2—C10—C9	123.21 (10)
C2—C3—H3	119.8 (8)	O2—C10—C11	116.53 (10)
C4—C3—H3	120.0 (8)	C9—C10—C11	120.26 (10)
C5—C4—C3	119.03 (10)	C12—C11—C10	119.88 (10)
C5—C4—N1	118.41 (9)	C12—C11—H10	121.0 (8)
C3—C4—N1	122.28 (10)	C10—C11—H10	119.1 (8)
C6—C5—C4	120.99 (10)	C11—C12—C13	120.38 (10)
C6—C5—H5	120.6 (8)	C11—C12—H11	118.1 (8)
C4—C5—H5	118.4 (8)	C13—C12—H11	121.5 (8)
C1—C6—C5	119.23 (10)	C12—C13—C8	120.02 (10)
C1—C6—H6	120.2 (8)	C12—C13—H12	120.2 (8)
C5—C6—H6	120.5 (8)	C8—C13—H12	119.8 (8)

C1ⁱ—O1—C1—C2	49.26 (9)	C4—N1—C7—C8	−171.34 (10)
C1ⁱ—O1—C1—C6	−131.68 (11)	N1—C7—C8—C13	175.25 (11)
C6—C1—C2—C3	1.91 (17)	N1—C7—C8—C9	−2.15 (18)
O1—C1—C2—C3	−179.04 (10)	C13—C8—C9—C10	−1.16 (16)
C1—C2—C3—C4	−0.10 (18)	C7—C8—C9—C10	176.18 (10)
C2—C3—C4—C5	−0.88 (17)	C8—C9—C10—O2	−179.55 (10)
C2—C3—C4—N1	173.02 (10)	C8—C9—C10—C11	0.54 (16)
C7—N1—C4—C5	−145.80 (11)	O2—C10—C11—C12	−179.50 (10)
C7—N1—C4—C3	40.26 (15)	C9—C10—C11—C12	0.42 (17)
C3—C4—C5—C6	0.06 (16)	C10—C11—C12—C13	−0.76 (17)
N1—C4—C5—C6	−174.08 (10)	C11—C12—C13—C8	0.15 (17)
C2—C1—C6—C5	−2.71 (16)	C9—C8—C13—C12	0.82 (17)
O1—C1—C6—C5	178.23 (9)	C7—C8—C13—C12	−176.66 (10)
C4—C5—C6—C1	1.72 (16)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1ⁱⁱ	0.972 (19)	1.828 (19)	2.7615 (12)	160.1 (16)
C5—H5···O2ⁱⁱⁱ	0.973 (13)	2.431 (14)	3.1121 (14)	126.7 (10)
C12—H11···Cg1ⁱⁱⁱ	1.004 (14)	2.986 (15)	3.9882 (12)	178.7 (19)

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

Short intermolecular contacts (Å) in the title structure top

Contact	Distance	Symmetry operation
H12···O1	2.763 (14)	1 - x, 2 - y, 1 - z
H6···H11	2.53 (2)	x, 2 - y, -1/2 + z
C3···C6	3.5155 (15)	x, -1 + y, z
C6···H11	2.892 (15)	x, 1 - y, -1/2 + z
C11···C11	3.319 (2)	1/2 - x, 1/2 - y, 1 - z
H11···H2	2.40 (3)	1 - x, 1 - y, 1 - z

Funding information

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

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