organic compounds
N′-[(1E)-4-Bromobenzylidene]-5-phenyl-1H-pyrazole-3-carbohydrazide
aMedicinal Chemistry Laboratory, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, bLCAE, Department of Chemistry, Faculty of Sciences, University Mohamed I, Oujda, Morocco, and cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: yramli76@yahoo.fr
In the title compound, C17H13BrN4O, the dihedral angles between the pyrazole ring and the pedant phenyl and bromobenzene rings are 21.61 (11) and 28.09 (11)°, respectively. In the crystal, N—H⋯O hydrogen bonds link the molecules into [010] chains, which are reinforced by C—H⋯O interactions.
Keywords: crystal structure; pyrazole derivatives; C—H ⋯O hydrogen bonds.
CCDC reference: 1481143
Structure description
As a continuation of our studies of pyrazole carbohydrazides (Karrouchi et al., 2015), we have studied the action of 4-bromobenzaldehyde towards 5-phenyl-1H-pyrazole-3-carbohydrazide. This readily leads to the title compound (Fig. 1) in good yield. The molecule is distinctly twisted from end to end as indicated by the dihedral angle of 21.61 (7)° between the pendant C1–C6 phenyl ring and the pyrazole ring, and the angle of 28.10 (7)° between the latter and the C12–C17 benzene ring.
In the crystal, a N1—H1A⋯O1 hydrogen bond links the molecules into chains running parallel to [010] (Table 1 and Fig. 2) with the chains stacking along the c axis direction (Fig. 3). The chain linkage is reinfoced by a weak C—H⋯O interaction.
Synthesis and crystallization
To a solution of 5-phenyl-1H-pyrazole-3-carbohydrazide (1 mmol, 250 mg) in 10 ml of ethanol, was added an equimolar amount of the 4-bromobenzaldehyde in the presence of acetic acid. The mixture was maintained under reflux for 2 h, until TLC indicated the end of reaction. Then, the mixture as poured into cold water, and the precipitate formed was filtered out washed with ethanol. Single crystals of the title compound were obtained on slow evaporation of the solvent (DMF). Yield 85%; m.p. 294–296°C
Refinement
Crystal data, data collection and structure . The methyl group is rotationally disordered over two distinct sites. The two orientations were restrained to have comparable geometries.
details are summarized in Table 2Structural data
CCDC reference: 1481143
10.1107/S2414314616008300/hb4044sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616008300/hb4044Isup2.hkl
To a solution of 5-phenyl-1H-pyrazole-3-carbohydrazide (1 mmol, 250 mg) in 10 ml of ethanol, was added an equimolar amount of the 4-bromobenzaldehyde in the presence of acetic acid. The mixture was maintained under reflux for 2 h, until TLC indicated the end of reaction. Then, the mixture as poured into cold water, and the precipitate formed was filtered out washed with ethanol. Single crystals of the title compound were obtained on slow evaporation of the solvent (DMF). Yield 85%; m.p. 294–296°C
Crystal data, data collection and structure
details are summarized in Table 2. The methyl group is rotationally disordered over two distinct sites. The two orientations were restrained to have comparable geometries.As a continuation of our studies of pyrazole carbohydrazides (Karrouchi et al., 2015), we have studied the action of 4-bromobenzaldehyde towards 5-phenyl-1H-pyrazole-3-carbohydrazide. This readily leads to the title compound (Fig. 1) in good yield. The molecule is distinctly twisted from end to end as indicated by the dihedral angle of 21.61 (7)° between the C1–C6 benzene ring and the pyrazole ring, and the angle of 28.10 (7)° between the latter and the C12–C17 benzene ring.
In the crystal, a N1—H1A···O1 hydrogen bond links the molecules into chains running parallel to [010] (Table 1 and Fig. 2) with the chains stacking along the c axis direction (Fig. 3). The chain linkage is reinfoced by a weak C—H···O interaction.
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).Fig. 1. The title molecule with labeling scheme and 50% probability ellipsoids. | |
Fig. 2. A portion of one chain viewed along the c axis with the N—H···O hydrogen bonds shown as dotted lines. | |
Fig. 3. Packing viewed along the b axis showing a stack of hydrogen-bonded chains. |
C17H13BrN4O | F(000) = 744 |
Mr = 369.22 | Dx = 1.622 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 15.5151 (3) Å | Cell parameters from 9982 reflections |
b = 7.1752 (1) Å | θ = 3.0–72.1° |
c = 14.4593 (3) Å | µ = 3.79 mm−1 |
β = 110.072 (1)° | T = 150 K |
V = 1511.90 (5) Å3 | Plate, colourless |
Z = 4 | 0.20 × 0.08 × 0.02 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 2958 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 2704 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.040 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.1°, θmin = 3.0° |
ω scans | h = −19→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −8→8 |
Tmin = 0.74, Tmax = 0.93 | l = −17→16 |
19026 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)] = 0.030 | Hydrogen site location: mixed |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0406P)2 + 1.1336P] where P = (Fo2 + 2Fc2)/3 |
2958 reflections | (Δ/σ)max = 0.001 |
216 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C17H13BrN4O | V = 1511.90 (5) Å3 |
Mr = 369.22 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 15.5151 (3) Å | µ = 3.79 mm−1 |
b = 7.1752 (1) Å | T = 150 K |
c = 14.4593 (3) Å | 0.20 × 0.08 × 0.02 mm |
β = 110.072 (1)° |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 2958 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | 2704 reflections with I > 2σ(I) |
Tmin = 0.74, Tmax = 0.93 | Rint = 0.040 |
19026 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.63 e Å−3 |
2958 reflections | Δρmin = −0.42 e Å−3 |
216 parameters |
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) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. The methyl group is rotationally disordered over two distinct sites. The two orientations were restrained to have comparable geometries and included as riding contributions. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.08242 (2) | 1.44181 (3) | 0.40787 (2) | 0.03152 (10) | |
O1 | 0.55572 (10) | 0.7240 (2) | 0.39651 (12) | 0.0274 (3) | |
N1 | 0.56205 (12) | 0.1066 (2) | 0.36792 (13) | 0.0209 (3) | |
H1A | 0.548 (2) | −0.014 (4) | 0.372 (2) | 0.037 (7)* | |
N2 | 0.50212 (11) | 0.2396 (2) | 0.37161 (12) | 0.0207 (3) | |
N3 | 0.41822 (12) | 0.5828 (2) | 0.37237 (13) | 0.0208 (3) | |
H3A | 0.3856 (19) | 0.477 (4) | 0.3598 (19) | 0.029 (7)* | |
N4 | 0.37729 (12) | 0.7495 (2) | 0.37822 (12) | 0.0216 (3) | |
C1 | 0.72343 (14) | 0.0664 (3) | 0.36873 (14) | 0.0201 (4) | |
C2 | 0.81039 (14) | 0.1483 (3) | 0.40431 (15) | 0.0248 (4) | |
H2 | 0.8169 | 0.2714 | 0.4300 | 0.030* | |
C3 | 0.88713 (15) | 0.0518 (3) | 0.40256 (17) | 0.0300 (5) | |
H3 | 0.9459 | 0.1090 | 0.4271 | 0.036* | |
C4 | 0.87849 (15) | −0.1286 (3) | 0.36503 (16) | 0.0289 (5) | |
H4 | 0.9311 | −0.1948 | 0.3637 | 0.035* | |
C5 | 0.79246 (15) | −0.2107 (3) | 0.32966 (15) | 0.0254 (4) | |
H5 | 0.7863 | −0.3337 | 0.3039 | 0.030* | |
C6 | 0.71507 (14) | −0.1153 (3) | 0.33133 (15) | 0.0219 (4) | |
H6 | 0.6565 | −0.1733 | 0.3071 | 0.026* | |
C7 | 0.64455 (13) | 0.1770 (3) | 0.37096 (14) | 0.0196 (4) | |
C8 | 0.63687 (14) | 0.3686 (3) | 0.37568 (15) | 0.0208 (4) | |
H8 | 0.6821 | 0.4596 | 0.3781 | 0.025* | |
C9 | 0.54810 (14) | 0.3990 (3) | 0.37609 (15) | 0.0194 (4) | |
C10 | 0.50863 (14) | 0.5828 (3) | 0.38258 (14) | 0.0198 (4) | |
C11 | 0.28977 (14) | 0.7463 (3) | 0.35493 (15) | 0.0218 (4) | |
H11 | 0.2566 | 0.6344 | 0.3322 | 0.026* | |
C12 | 0.24174 (14) | 0.9165 (3) | 0.36375 (14) | 0.0207 (4) | |
C13 | 0.14574 (14) | 0.9207 (3) | 0.32523 (15) | 0.0226 (4) | |
H13 | 0.1129 | 0.8155 | 0.2910 | 0.027* | |
C14 | 0.09828 (14) | 1.0785 (3) | 0.33688 (15) | 0.0234 (4) | |
H14 | 0.0332 | 1.0824 | 0.3103 | 0.028* | |
C15 | 0.14737 (14) | 1.2290 (3) | 0.38761 (15) | 0.0223 (4) | |
C16 | 0.24238 (14) | 1.2301 (3) | 0.42531 (15) | 0.0234 (4) | |
H16 | 0.2746 | 1.3359 | 0.4596 | 0.028* | |
C17 | 0.28952 (14) | 1.0742 (3) | 0.41216 (15) | 0.0223 (4) | |
H17 | 0.3547 | 1.0742 | 0.4361 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.03319 (15) | 0.02154 (14) | 0.03802 (15) | 0.00873 (9) | 0.00988 (10) | −0.00237 (9) |
O1 | 0.0251 (7) | 0.0134 (7) | 0.0448 (9) | −0.0016 (6) | 0.0134 (7) | −0.0016 (6) |
N1 | 0.0225 (8) | 0.0126 (8) | 0.0281 (9) | 0.0014 (6) | 0.0093 (7) | 0.0000 (7) |
N2 | 0.0210 (8) | 0.0128 (8) | 0.0276 (9) | 0.0022 (6) | 0.0074 (7) | −0.0008 (6) |
N3 | 0.0209 (8) | 0.0136 (8) | 0.0283 (9) | 0.0006 (6) | 0.0092 (7) | −0.0029 (7) |
N4 | 0.0251 (9) | 0.0160 (8) | 0.0238 (8) | 0.0044 (6) | 0.0084 (7) | −0.0005 (6) |
C1 | 0.0222 (10) | 0.0191 (10) | 0.0199 (9) | 0.0035 (7) | 0.0084 (8) | 0.0012 (7) |
C2 | 0.0264 (10) | 0.0211 (10) | 0.0264 (11) | −0.0006 (8) | 0.0082 (8) | −0.0053 (8) |
C3 | 0.0214 (10) | 0.0364 (13) | 0.0319 (11) | 0.0007 (9) | 0.0088 (9) | −0.0039 (9) |
C4 | 0.0273 (11) | 0.0324 (12) | 0.0294 (11) | 0.0088 (9) | 0.0127 (9) | 0.0007 (9) |
C5 | 0.0320 (11) | 0.0218 (10) | 0.0247 (10) | 0.0056 (8) | 0.0128 (9) | 0.0006 (8) |
C6 | 0.0267 (10) | 0.0183 (9) | 0.0217 (10) | 0.0008 (8) | 0.0097 (8) | 0.0009 (8) |
C7 | 0.0216 (9) | 0.0166 (9) | 0.0208 (9) | 0.0018 (7) | 0.0077 (7) | 0.0002 (7) |
C8 | 0.0230 (10) | 0.0136 (9) | 0.0271 (10) | 0.0000 (7) | 0.0103 (8) | 0.0011 (7) |
C9 | 0.0227 (9) | 0.0127 (9) | 0.0227 (9) | 0.0007 (7) | 0.0076 (8) | 0.0000 (7) |
C10 | 0.0214 (9) | 0.0163 (9) | 0.0221 (9) | 0.0012 (7) | 0.0079 (8) | 0.0009 (7) |
C11 | 0.0235 (10) | 0.0188 (10) | 0.0234 (10) | −0.0002 (8) | 0.0085 (8) | −0.0009 (8) |
C12 | 0.0231 (10) | 0.0200 (10) | 0.0206 (9) | 0.0032 (7) | 0.0096 (8) | 0.0024 (7) |
C13 | 0.0216 (10) | 0.0202 (10) | 0.0264 (10) | −0.0028 (7) | 0.0086 (8) | −0.0024 (8) |
C14 | 0.0202 (9) | 0.0248 (10) | 0.0258 (10) | 0.0020 (8) | 0.0086 (8) | 0.0014 (8) |
C15 | 0.0265 (10) | 0.0189 (10) | 0.0224 (10) | 0.0033 (8) | 0.0094 (8) | 0.0024 (8) |
C16 | 0.0258 (10) | 0.0197 (10) | 0.0228 (10) | −0.0012 (8) | 0.0059 (8) | 0.0005 (8) |
C17 | 0.0209 (9) | 0.0235 (10) | 0.0213 (9) | 0.0012 (8) | 0.0055 (8) | 0.0010 (8) |
Br1—C15 | 1.907 (2) | C5—C6 | 1.389 (3) |
O1—C10 | 1.225 (2) | C5—H5 | 0.9500 |
N1—N2 | 1.346 (2) | C6—H6 | 0.9500 |
N1—C7 | 1.362 (3) | C7—C8 | 1.384 (3) |
N1—H1A | 0.90 (3) | C8—C9 | 1.397 (3) |
N2—C9 | 1.338 (3) | C8—H8 | 0.9500 |
N3—C10 | 1.359 (3) | C9—C10 | 1.470 (3) |
N3—N4 | 1.370 (2) | C11—C12 | 1.459 (3) |
N3—H3A | 0.90 (3) | C11—H11 | 0.9500 |
N4—C11 | 1.282 (3) | C12—C13 | 1.400 (3) |
C1—C2 | 1.398 (3) | C12—C17 | 1.401 (3) |
C1—C6 | 1.400 (3) | C13—C14 | 1.392 (3) |
C1—C7 | 1.468 (3) | C13—H13 | 0.9500 |
C2—C3 | 1.385 (3) | C14—C15 | 1.379 (3) |
C2—H2 | 0.9500 | C14—H14 | 0.9500 |
C3—C4 | 1.392 (3) | C15—C16 | 1.385 (3) |
C3—H3 | 0.9500 | C16—C17 | 1.385 (3) |
C4—C5 | 1.386 (3) | C16—H16 | 0.9500 |
C4—H4 | 0.9500 | C17—H17 | 0.9500 |
N2—N1—C7 | 112.98 (16) | C7—C8—H8 | 127.5 |
N2—N1—H1A | 119.1 (19) | C9—C8—H8 | 127.5 |
C7—N1—H1A | 127.4 (19) | N2—C9—C8 | 112.11 (17) |
C9—N2—N1 | 104.11 (15) | N2—C9—C10 | 122.89 (18) |
C10—N3—N4 | 118.45 (16) | C8—C9—C10 | 125.00 (18) |
C10—N3—H3A | 120.8 (17) | O1—C10—N3 | 123.57 (18) |
N4—N3—H3A | 120.7 (17) | O1—C10—C9 | 120.95 (18) |
C11—N4—N3 | 116.10 (17) | N3—C10—C9 | 115.48 (17) |
C2—C1—C6 | 118.90 (18) | N4—C11—C12 | 119.27 (19) |
C2—C1—C7 | 118.12 (18) | N4—C11—H11 | 120.4 |
C6—C1—C7 | 122.97 (19) | C12—C11—H11 | 120.4 |
C3—C2—C1 | 120.7 (2) | C13—C12—C17 | 119.30 (18) |
C3—C2—H2 | 119.6 | C13—C12—C11 | 119.27 (18) |
C1—C2—H2 | 119.7 | C17—C12—C11 | 121.41 (18) |
C2—C3—C4 | 120.2 (2) | C14—C13—C12 | 120.29 (19) |
C2—C3—H3 | 119.9 | C14—C13—H13 | 119.9 |
C4—C3—H3 | 119.9 | C12—C13—H13 | 119.9 |
C5—C4—C3 | 119.4 (2) | C15—C14—C13 | 118.87 (19) |
C5—C4—H4 | 120.3 | C15—C14—H14 | 120.6 |
C3—C4—H4 | 120.3 | C13—C14—H14 | 120.6 |
C4—C5—C6 | 120.8 (2) | C14—C15—C16 | 122.17 (19) |
C4—C5—H5 | 119.6 | C14—C15—Br1 | 118.98 (15) |
C6—C5—H5 | 119.6 | C16—C15—Br1 | 118.84 (16) |
C5—C6—C1 | 119.9 (2) | C17—C16—C15 | 118.86 (19) |
C5—C6—H6 | 120.0 | C17—C16—H16 | 120.6 |
C1—C6—H6 | 120.0 | C15—C16—H16 | 120.6 |
N1—C7—C8 | 105.89 (17) | C16—C17—C12 | 120.46 (19) |
N1—C7—C1 | 125.45 (18) | C16—C17—H17 | 119.8 |
C8—C7—C1 | 128.65 (19) | C12—C17—H17 | 119.8 |
C7—C8—C9 | 104.91 (17) | ||
C7—N1—N2—C9 | 0.6 (2) | C7—C8—C9—C10 | 178.65 (19) |
C10—N3—N4—C11 | 170.82 (18) | N4—N3—C10—O1 | −0.2 (3) |
C6—C1—C2—C3 | 0.1 (3) | N4—N3—C10—C9 | 179.64 (17) |
C7—C1—C2—C3 | −178.9 (2) | N2—C9—C10—O1 | 172.58 (19) |
C1—C2—C3—C4 | 0.1 (3) | C8—C9—C10—O1 | −6.2 (3) |
C2—C3—C4—C5 | −0.1 (3) | N2—C9—C10—N3 | −7.3 (3) |
C3—C4—C5—C6 | −0.1 (3) | C8—C9—C10—N3 | 173.97 (19) |
C4—C5—C6—C1 | 0.3 (3) | N3—N4—C11—C12 | 177.16 (17) |
C2—C1—C6—C5 | −0.3 (3) | N4—C11—C12—C13 | 170.84 (19) |
C7—C1—C6—C5 | 178.70 (18) | N4—C11—C12—C17 | −10.8 (3) |
N2—N1—C7—C8 | −0.8 (2) | C17—C12—C13—C14 | −1.4 (3) |
N2—N1—C7—C1 | 179.63 (18) | C11—C12—C13—C14 | 176.94 (18) |
C2—C1—C7—N1 | −159.20 (19) | C12—C13—C14—C15 | −0.6 (3) |
C6—C1—C7—N1 | 21.8 (3) | C13—C14—C15—C16 | 1.6 (3) |
C2—C1—C7—C8 | 21.3 (3) | C13—C14—C15—Br1 | −177.73 (15) |
C6—C1—C7—C8 | −157.7 (2) | C14—C15—C16—C17 | −0.5 (3) |
N1—C7—C8—C9 | 0.6 (2) | Br1—C15—C16—C17 | 178.84 (15) |
C1—C7—C8—C9 | −179.86 (19) | C15—C16—C17—C12 | −1.6 (3) |
N1—N2—C9—C8 | −0.2 (2) | C13—C12—C17—C16 | 2.6 (3) |
N1—N2—C9—C10 | −179.13 (18) | C11—C12—C17—C16 | −175.78 (18) |
C7—C8—C9—N2 | −0.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N2 | 0.90 (3) | 2.45 (3) | 2.787 (2) | 103 (2) |
N1—H1A···O1i | 0.90 (3) | 1.91 (3) | 2.783 (2) | 163 (3) |
C6—H6···O1i | 0.95 | 2.46 | 3.151 (3) | 130 |
Symmetry code: (i) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N2 | 0.90 (3) | 2.45 (3) | 2.787 (2) | 103 (2) |
N1—H1A···O1i | 0.90 (3) | 1.91 (3) | 2.783 (2) | 163 (3) |
C6—H6···O1i | 0.95 | 2.46 | 3.151 (3) | 130 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C17H13BrN4O |
Mr | 369.22 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 15.5151 (3), 7.1752 (1), 14.4593 (3) |
β (°) | 110.072 (1) |
V (Å3) | 1511.90 (5) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 3.79 |
Crystal size (mm) | 0.20 × 0.08 × 0.02 |
Data collection | |
Diffractometer | Bruker D8 VENTURE PHOTON 100 CMOS |
Absorption correction | Multi-scan (SADABS; Bruker, 2016) |
Tmin, Tmax | 0.74, 0.93 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19026, 2958, 2704 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.076, 1.04 |
No. of reflections | 2958 |
No. of parameters | 216 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.63, −0.42 |
Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), DIAMOND (Brandenburg & Putz, 2012), SHELXTL (Sheldrick, 2008).
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
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