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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 9| September 2016| x161481
doi:10.1107/S2414314616014814

Histamine perchlorate

Ugochukwu Okeke,a Yilma Gultneh,a Jerry P. Jasinskib and Ray J. Butchera*

aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435, USA
*Correspondence e-mail: rbutcher99@yahoo.com

Edited by P. C. Healy, Griffith University, Australia (Received 16 September 2016; accepted 19 September 2016; online 23 September 2016)

The perchlorate salt of the histamine dication [systematic name: 4-(2-aza­niumyleth­yl)-1H-imidazol-3-ium bis(perchlorate)], C5H11N32+·2ClO4−, crystallizes in the monoclinic space group P21/c with two formula units in the asymmetric unit. One of the histamine dications is disordered [occupancies of 0.718 (4) and 0.282 (4)] and two of the four perchlorate anions are disordered [occupancies of 0.735 (6):0.265 (6) and 0.637 (5):0.363 (5)]. There is extensive hydrogen bonding in the structure involving both N—H⋯O and C—H⋯O inter­actions, which link the histamine dications and perchlorate anions into a three-dimensional array.

CCDC reference: 1505211

Similar articles
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[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Histamine is a biologically important compound in the body's immune system (Schneider et al., 2014[Schneider, H. E., Neumann, D. & Seifert, R. (2014). Neurosci. Biobehav. Rev. 47, 101-121.]). It contains an imidazole group which is a nitro­genous aromatic compound found in enzymes and in various drugs (Zlomuzica et al., 2016[Zlomuzica, A., Dere, D., Binder, S., De Souza, S., Maria, A., Huston, J. P. & Dere, E. (2016). Neuropharmacology, 106, 135-145.]). Histamines are of inter­est spanning a wide variety of topics, including drug therapeutics (Zlomuzica et al., 2016[Zlomuzica, A., Dere, D., Binder, S., De Souza, S., Maria, A., Huston, J. P. & Dere, E. (2016). Neuropharmacology, 106, 135-145.]), cancer (Martinel Lamas et al., 2015[Martinel Lamas, D. J., Nicoud, M. B., Sterle, H. A., Cremaschi, G. A. & Medina, V. A. (2015). Cell Death Dis. 6, e2029.]), addictions (Nuutinen et al., 2016[Nuutinen, S., Maki, T., Rozov, S., Backstrom, P., Hyytia, P., Piepponen, P. & Panula, P. (2016). Neuropharmacology, 106, 156-163.]), and autoimmune (Abiuso et al., 2014[Abiuso, A. M. B., Berensztein, E., Pagotto, R. M., Pereyra, E. N., Medina, V., Lamas, D. J. M., Moreno, M. B., Pignataro, O. P. & Mondillo, C. (2014). J. Endocrinol. 223, 241-253.]) and anxiety disorders (Cacabelos et al., 2016[Cacabelos, R., Torrellas, C., Fernandez-Novoa, L. & Aliev, G. (2016). Curr. Pharm. Des. 22, 819-848.]). In view of this inter­est in histamine, several structures of histamine salts have been determined through X-ray crystallography previously containing both histamine dications (Veidis et al., 1969[Veidis, M. V., Palenik, G. J., Schaffrin, R. & Trotter, J. (1969). J. Chem. Soc. A, pp. 2659-2666.]; Yamane et al., 1973[Yamane, T., Ashida, T. & Kakudo, M. (1973). Acta Cryst. B29, 2884-2891.]) and histamine cations (Prout et al., 1974[Prout, K., Critchley, S. R. & Ganellin, C. R. (1974). Acta Cryst. B30, 2884-2886.]; Belfilali et al., 2015[Belfilali, I., Yebdri, S., Louhibi, S., Boukli-hacene, L. & Roisnel, T. (2015). Acta Cryst. E71, o301-o302.]).

The present report contains the structure of the perchlorate salt of histamine in the diprotonated form, which crystallizes in the monoclinic space group P21/c with two formula units in the asymmetric unit (Fig. 1[link]). One of the histamine dications is disordered [occupancies of 0.718 (4) and 0.282 (4)] and two of the four perchlorate anions are disordered [occupancies of 0.735 (6):0.265 (6) and 0.637 (5):0.363 (5)]. The metrical parameters of the diprotonated imidazolium ring are similar to those found for the phosphate (Veidis et al., 1969[Veidis, M. V., Palenik, G. J., Schaffrin, R. & Trotter, J. (1969). J. Chem. Soc. A, pp. 2659-2666.]) and sulfate analogs (Yamane et al., 1973[Yamane, T., Ashida, T. & Kakudo, M. (1973). Acta Cryst. B29, 2884-2891.]). It has been suggested (Kier, 1968[Kier, L. B. (1968). J. Med. Chem. 11, 441-445.]) that the dual activity of histamine is a consequence of the ability of its monocation to adopt two distinct preferred conformations, viz. trans and gauche rotamers involving the ethanamine substituent. In the title compound, there are two independent histamine dications and one of them is disordered over two conformations. The three C3—C4—C5—N3 torsion angles are −64.3 (5), 59.4 (7), and −50 (2)°. These values are in contrast to the values reported in the two structures containing histamine cations where these torsion angles are 177.3 (Prout et al., 1974[Prout, K., Critchley, S. R. & Ganellin, C. R. (1974). Acta Cryst. B30, 2884-2886.]) and 176.22 (10)° (Belfilali et al., 2015[Belfilali, I., Yebdri, S., Louhibi, S., Boukli-hacene, L. & Roisnel, T. (2015). Acta Cryst. E71, o301-o302.]).

[Figure 1]
Figure 1
Diagram showing the histamine dication and perchlorate anions (major component only for disordered species) and the atom labeling. Atomic displacement parameters are at the 50% probability level. N—H⋯O and C—H⋯O hydrogen-bond inter­actions are indicated by dashed bonds.

There is extensive hydrogen bonding in the structure, involving both N—H⋯O and C—H⋯O inter­actions, which link the histamine dications and perchlorate anions into a three-dimensional array (Table 1[link] and Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1A—H1A⋯O13i 0.88 2.50 3.337 (4) 160
N1A—H1A⋯O14i 0.88 2.49 3.052 (4) 122
N1A—H1A⋯O43ii 0.88 2.47 3.021 (7) 121
N1A—H1A⋯O41Aii 0.88 2.36 2.978 (9) 127
N2A—H2A⋯Cl4 0.88 2.96 3.709 (3) 145
N2A—H2A⋯O41 0.88 2.03 2.907 (9) 171
N2A—H2A⋯O44A 0.88 2.08 2.95 (2) 168
N3A—H3A1⋯O21iii 0.91 2.56 3.040 (4) 114
N3A—H3A1⋯O34iv 0.91 2.23 3.065 (6) 153
N3A—H3A1⋯O33Aiv 0.91 2.11 2.861 (12) 139
N3A—H3A2⋯Cl1v 0.91 2.98 3.742 (3) 143
N3A—H3A2⋯O11v 0.91 2.45 3.031 (4) 122
N3A—H3A2⋯O12v 0.91 2.44 3.232 (4) 146
N3A—H3A2⋯O42v 0.91 2.53 3.207 (8) 131
N3A—H3A2⋯O42Av 0.91 2.57 3.272 (14) 134
N3A—H3A3⋯Cl3 0.91 2.95 3.735 (3) 145
N3A—H3A3⋯O31 0.91 2.51 3.055 (8) 119
N3A—H3A3⋯O32 0.91 2.26 3.120 (8) 159
N3A—H3A3⋯O32A 0.91 2.14 3.04 (2) 170
C2A—H2AA⋯O14i 0.95 2.65 3.129 (5) 112
C2A—H2AA⋯O22 0.95 2.40 3.074 (5) 128
C4A—H4AB⋯O43ii 0.99 2.66 3.379 (8) 129
C5A—H5AA⋯O42v 0.99 2.70 3.158 (9) 109
C5A—H5AA⋯O43v 0.99 2.70 3.310 (7) 120
C5A—H5AB⋯O12vi 0.99 2.61 3.542 (5) 158
N1B—H1B⋯Cl1 0.88 2.91 3.714 (5) 153
N1B—H1B⋯O12 0.88 2.39 3.265 (6) 171
N1B—H1B⋯O14 0.88 2.38 2.961 (6) 124
N2B—H2B⋯O32 0.88 2.10 2.939 (9) 159
N3B—H3B1⋯Cl4 0.91 2.94 3.695 (14) 142
N3B—H3B1⋯O41 0.91 2.05 2.937 (19) 163
N3B—H3B1⋯O42 0.91 2.65 3.168 (13) 117
N3B—H3B2⋯O11vii 0.91 2.56 3.120 (14) 120
N3B—H3B2⋯O13vii 0.91 2.45 3.269 (11) 150
N3B—H3B2⋯O31viii 0.91 2.63 3.310 (14) 132
N3B—H3B3⋯O21 0.91 2.36 2.910 (10) 119
N3B—H3B3⋯O34ix 0.91 2.56 3.374 (13) 150
C1B—H1BA⋯O24ix 0.95 2.64 3.441 (7) 142
C2B—H2BA⋯O22iii 0.95 2.50 3.024 (6) 115
C4B—H4BB⋯O33ix 0.99 2.50 3.433 (8) 156
C5B—H5BA⋯O11x 0.99 2.52 3.249 (10) 130
N2BA—H2B1⋯O22iii 0.88 2.38 3.150 (15) 146
N3BA—H3B4⋯Cl1vii 0.91 2.78 3.62 (3) 155
N3BA—H3B4⋯O11vii 0.91 2.15 2.93 (4) 144
N3BA—H3B4⋯O13vii 0.91 2.40 3.12 (3) 137
N3BA—H3B4⋯O31Aviii 0.91 2.59 3.14 (4) 120
N3BA—H3B5⋯Cl2 0.91 2.82 3.66 (3) 154
N3BA—H3B5⋯O21 0.91 2.13 2.83 (2) 133
N3BA—H3B5⋯O24 0.91 2.48 3.29 (4) 149
N3BA—H3B6⋯Cl4 0.91 2.87 3.77 (4) 168
N3BA—H3B6⋯O44A 0.91 2.28 3.07 (5) 146
C1BA—H1BB⋯O14 0.95 2.16 3.103 (17) 171
C2BA—H2BB⋯Cl3 0.95 2.75 3.644 (14) 157
C2BA—H2BB⋯O32A 0.95 2.46 3.12 (3) 127
C2BA—H2BB⋯O34A 0.95 2.09 3.04 (2) 173
C4BA—H4BD⋯O11x 0.99 2.56 3.250 (13) 127
C4BA—H4BC⋯O12 0.99 2.38 3.325 (16) 159
C5BA—H5BC⋯Cl3ix 0.99 2.98 3.86 (3) 149
C5BA—H5BC⋯O34Aix 0.99 2.26 3.18 (4) 153
C5BA—H5BD⋯O31Aviii 0.99 2.57 3.22 (4) 123
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (v) x-1, y, z; (vi) [x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (vii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (viii) x+1, y, z; (ix) -x+1, -y+1, -z; (x) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].
[Figure 2]
Figure 2
Packing diagram for the title compound, viewed along the b axis, showing the three-dimensional arrangement. N—H⋯O and C—H⋯O hydrogen-bond inter­actions are indicated by dashed bonds.

Synthesis and crystallization

Histamine hydro­chloride (0.3181 g, 1.728 mmol) was dissolved in 15 ml of methanol. Zn(ClO4)2·6H2O (0.6434 g, 1.728 mmol) was dissolved in 15 ml of methanol and added to the histamine hydro­chloride solution. The mixture was stirred at room temperature overnight. The methanol was removed by rotary evaporation. The product was crystallized by redissolving it in aceto­nitrile and layering the solution with diethyl ether. After ∼1 h, a colorless crystal formed. The crystal was allowed to grow overnight before gravity filtration, air drying, and collection of the crystallized product for XRD analysis.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. One of the histamine dications is disordered [occupancies of 0.718 (4) and 0.282 (4)] and both components were constrained to have similar metrical parameters. Two of the four perchlorate anions are also disordered [occupancies of 0.735 (6):0.265 (6) and 0.637 (5):0.363 (5)] and were constrained to be tetra­hedral.

Table 2
Experimental details

Crystal data
Chemical formula C5H11N32+·2ClO4−
Mr 312.07
Crystal system, space group Monoclinic, P21/c
Temperature (K) 173
a, b, c (Å) 11.3333 (6), 16.4178 (9), 12.7650 (6)
β (°) 94.140 (5)
V (Å3) 2369.0 (2)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.59
Crystal size (mm) 0.43 × 0.37 × 0.27
 
Data collection
Diffractometer Oxford Diffraction Xcalibur Eos Gemini
Absorption correction Multi-scan (CrysAlis PRO; Rigaku-Oxford Diffraction, 2015[Rigaku-Oxford Diffraction (2015). CrysAlis PRO and CrysAlis RED. Rigaku Americas Corporation, The Woodlands, Texas, USA.])
Tmin, Tmax 0.765, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 12472, 5581, 3463
Rint 0.034
(sin θ/λ)max (Å−1) 0.686
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.219, 1.07
No. of reflections 5581
No. of parameters 380
No. of restraints 450
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.91, −0.63
Computer programs: CrysAlis PRO (Rigaku-Oxford Diffraction, 2015[Rigaku-Oxford Diffraction (2015). CrysAlis PRO and CrysAlis RED. Rigaku Americas Corporation, The Woodlands, Texas, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

All of the H atoms were placed in calculated positions and then refined using the riding model, with C/N—H = 0.95 (CH), 0.88 (NH), 0.99 (CH2), or 0.91 Å (NH3). Isotropic displacement parameters for these atoms were set at 1.2 (CH, NH and CH2) or 1.5 (NH3) times Ueq of the parent atom. The H atoms for the idealized ammonium groups were refined as rotating groups.

Structural data

CCDC reference: 1505211

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616014814/hg4015sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616014814/hg4015Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616014814/hg4015Isup3.cml

checkCIF report


Computing details top

Data collection: CrysAlis PRO (Rigaku-Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku-Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku-Oxford Diffraction, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4-(2-Azaniumylethyl)-1H-imidazol-3-ium bis(perchlorate) top
Crystal data top
C5H11N32+·2ClO4−F(000) = 1280
Mr = 312.07Dx = 1.750 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.3333 (6) ÅCell parameters from 2709 reflections
b = 16.4178 (9) Åθ = 4.0–27.7°
c = 12.7650 (6) ŵ = 0.59 mm−1
β = 94.140 (5)°T = 173 K
V = 2369.0 (2) Å3Chunk, colorless
Z = 80.43 × 0.37 × 0.27 mm
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer		5581 independent reflections
Radiation source: fine-focus sealed X-ray tube3463 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.034
ω scansθmax = 29.2°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku-Oxford Diffraction, 2015)		h = −15→14
Tmin = 0.765, Tmax = 1.000k = −21→19
12472 measured reflectionsl = −17→14
Refinement top
Refinement on F2450 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.219 w = 1/[σ2(Fo2) + (0.1133P)2 + 0.5966P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
5581 reflectionsΔρmax = 0.91 e Å−3
380 parametersΔρmin = −0.63 e Å−3
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
xyzUiso*/UeqOcc. (<1)
Cl10.93140 (7)0.87376 (4)0.23249 (6)0.0358 (2)
O110.9819 (2)0.87540 (14)0.3395 (2)0.0543 (7)
O120.9664 (3)0.79992 (15)0.1841 (2)0.0615 (8)
O130.9715 (3)0.94274 (15)0.1778 (2)0.0636 (8)
O140.8045 (2)0.87571 (15)0.2327 (3)0.0640 (8)
Cl20.62291 (9)0.37350 (5)0.18816 (8)0.0497 (3)
O210.7507 (3)0.37336 (18)0.2093 (3)0.0798 (10)
O220.5747 (3)0.37663 (18)0.2888 (3)0.0847 (11)
O230.5902 (4)0.30024 (19)0.1372 (3)0.0986 (13)
O240.5900 (4)0.44327 (19)0.1284 (3)0.0987 (13)
Cl30.20743 (8)0.61832 (5)0.13100 (7)0.0455 (3)
O310.1200 (7)0.5955 (5)0.2027 (6)0.0676 (17)0.735 (12)
O320.2645 (6)0.6896 (4)0.1755 (6)0.0710 (17)0.735 (12)
O330.2975 (5)0.5553 (3)0.1305 (6)0.0752 (14)0.735 (12)
O340.1566 (5)0.6322 (5)0.0292 (4)0.0736 (15)0.735 (12)
O31A0.1243 (19)0.5737 (13)0.1863 (17)0.0676 (17)0.265 (12)
O32A0.2797 (19)0.6680 (11)0.2011 (15)0.0710 (17)0.265 (12)
O33A0.1424 (13)0.6683 (10)0.0529 (12)0.0752 (14)0.265 (12)
O34A0.2837 (12)0.5632 (9)0.0836 (13)0.0736 (15)0.265 (12)
Cl40.78058 (8)0.62532 (5)0.38789 (7)0.0487 (3)
O410.7113 (8)0.5720 (6)0.3164 (5)0.0618 (12)0.637 (8)
O420.8672 (6)0.6601 (4)0.3188 (6)0.0583 (16)0.637 (8)
O430.8519 (5)0.5664 (4)0.4510 (5)0.0800 (14)0.637 (8)
O440.6998 (6)0.6864 (4)0.4113 (7)0.100 (2)0.637 (8)
O41A0.8376 (8)0.6002 (7)0.4848 (6)0.0618 (12)0.363 (8)
O42A0.8479 (12)0.6845 (7)0.3473 (10)0.0583 (16)0.363 (8)
O43A0.6992 (9)0.6577 (7)0.4652 (8)0.0800 (14)0.363 (8)
O44A0.7187 (17)0.5708 (12)0.3267 (14)0.100 (2)0.363 (8)
N1A0.2935 (3)0.52105 (17)0.3947 (3)0.0501 (8)
H1A0.22740.49280.39040.060*
N2A0.4681 (3)0.5565 (2)0.3720 (3)0.0569 (8)
H2A0.54000.55700.35020.068*
N3A0.1315 (3)0.72364 (18)0.3767 (2)0.0496 (8)
H3A10.16190.76840.41100.074*
H3A20.06140.73680.34140.074*
H3A30.18310.70590.33030.074*
C1A0.4234 (4)0.6133 (2)0.4349 (3)0.0531 (10)
H1AA0.46380.65990.46320.064*
C2A0.3886 (4)0.5012 (3)0.3488 (3)0.0609 (11)
H2AA0.39810.45470.30600.073*
C3A0.3104 (3)0.5915 (2)0.4503 (3)0.0430 (8)
C4A0.2219 (4)0.6305 (3)0.5131 (3)0.0616 (11)
H4AA0.25930.67800.54980.074*
H4AB0.19990.59140.56740.074*
C5A0.1121 (4)0.6584 (3)0.4536 (3)0.0612 (11)
H5AA0.07460.61130.41600.073*
H5AB0.05630.67840.50400.073*
N1B0.7010 (4)0.7247 (4)0.1384 (6)0.0428 (10)0.718 (4)
H1B0.77020.74910.14500.051*0.718 (4)
N2B0.5215 (5)0.6944 (3)0.1579 (6)0.0585 (13)0.718 (4)
H2B0.45010.69530.18060.070*0.718 (4)
N3B0.8500 (14)0.5260 (5)0.1399 (9)0.0632 (17)0.718 (4)
H3B10.79640.54420.18420.095*0.718 (4)
H3B20.91940.51450.17730.095*0.718 (4)
H3B30.82190.48010.10690.095*0.718 (4)
C1B0.5590 (5)0.6422 (4)0.0889 (6)0.0502 (14)0.718 (4)
H1BA0.51310.60010.05510.060*0.718 (4)
C2B0.6104 (5)0.7464 (3)0.1882 (5)0.0560 (14)0.718 (4)
H2BA0.60690.79020.23650.067*0.718 (4)
C3B0.6760 (4)0.6593 (4)0.0743 (6)0.0369 (11)0.718 (4)
C4B0.7598 (6)0.6220 (3)0.0064 (4)0.0544 (13)0.718 (4)
H4BA0.78270.6633−0.04490.065*0.718 (4)
H4BB0.71900.5773−0.03370.065*0.718 (4)
C5B0.8697 (9)0.5887 (5)0.0620 (8)0.0580 (19)0.718 (4)
H5BA0.92000.56550.00910.070*0.718 (4)
H5BB0.91410.63410.09730.070*0.718 (4)
N1BA0.6110 (10)0.6215 (6)0.0500 (9)0.0428 (10)0.282 (4)
H1B10.60610.58020.00600.051*0.282 (4)
N2BA0.5560 (13)0.7150 (10)0.1540 (16)0.0585 (13)0.282 (4)
H2B10.51310.74590.19290.070*0.282 (4)
N3BA0.861 (4)0.5172 (14)0.142 (2)0.0632 (17)0.282 (4)
H3B40.92980.49110.16160.095*0.282 (4)
H3B50.80230.47990.12900.095*0.282 (4)
H3B60.84140.55060.19540.095*0.282 (4)
C1BA0.6727 (14)0.7246 (14)0.137 (2)0.0502 (14)0.282 (4)
H1BB0.72090.76800.16420.060*0.282 (4)
C2BA0.5214 (13)0.6495 (11)0.1002 (17)0.0560 (14)0.282 (4)
H2BB0.44450.62620.09790.067*0.282 (4)
C3BA0.7112 (11)0.6643 (12)0.0744 (18)0.0369 (11)0.282 (4)
C4BA0.8326 (12)0.6508 (8)0.0449 (12)0.0544 (13)0.282 (4)
H4BC0.88680.68380.09220.065*0.282 (4)
H4BD0.83840.6718−0.02730.065*0.282 (4)
C5BA0.875 (3)0.5654 (13)0.048 (2)0.0580 (19)0.282 (4)
H5BC0.83440.5362−0.01180.070*0.282 (4)
H5BD0.96050.56620.03630.070*0.282 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0371 (4)0.0371 (4)0.0329 (4)−0.0003 (3)−0.0002 (3)−0.0012 (3)
O110.0487 (16)0.0773 (19)0.0359 (14)0.0074 (12)−0.0038 (12)−0.0022 (11)
O120.086 (2)0.0446 (14)0.0553 (16)0.0066 (13)0.0168 (15)−0.0084 (12)
O130.086 (2)0.0480 (15)0.0568 (17)−0.0153 (14)0.0066 (15)0.0095 (12)
O140.0365 (15)0.074 (2)0.080 (2)0.0016 (12)−0.0089 (14)0.0016 (14)
Cl20.0541 (6)0.0417 (5)0.0543 (6)−0.0012 (4)0.0103 (5)−0.0003 (4)
O210.0537 (19)0.093 (3)0.095 (3)−0.0011 (14)0.0224 (18)0.0046 (17)
O220.074 (2)0.106 (3)0.078 (2)0.0017 (16)0.0317 (19)−0.0042 (17)
O230.131 (3)0.0587 (18)0.104 (3)−0.0135 (19)−0.012 (2)−0.0211 (18)
O240.118 (3)0.0599 (19)0.114 (3)0.0027 (19)−0.022 (2)0.0284 (19)
Cl30.0448 (5)0.0536 (5)0.0378 (5)−0.0062 (4)0.0013 (4)−0.0008 (4)
O310.064 (2)0.089 (4)0.051 (3)−0.021 (3)0.0095 (18)0.003 (3)
O320.061 (3)0.067 (3)0.085 (4)−0.013 (3)0.002 (2)−0.012 (3)
O330.092 (3)0.075 (2)0.058 (3)0.018 (2)0.005 (2)0.002 (2)
O340.075 (3)0.103 (4)0.043 (2)0.002 (2)−0.0017 (19)0.005 (2)
O31A0.064 (2)0.089 (4)0.051 (3)−0.021 (3)0.0095 (18)0.003 (3)
O32A0.061 (3)0.067 (3)0.085 (4)−0.013 (3)0.002 (2)−0.012 (3)
O33A0.092 (3)0.075 (2)0.058 (3)0.018 (2)0.005 (2)0.002 (2)
O34A0.075 (3)0.103 (4)0.043 (2)0.002 (2)−0.0017 (19)0.005 (2)
Cl40.0430 (5)0.0639 (6)0.0390 (5)−0.0147 (4)0.0025 (4)−0.0020 (4)
O410.050 (2)0.093 (3)0.042 (2)−0.033 (2)0.0045 (18)−0.017 (2)
O420.048 (3)0.073 (4)0.054 (4)−0.015 (3)0.005 (2)0.011 (3)
O430.084 (3)0.093 (3)0.062 (3)−0.012 (2)0.001 (2)−0.002 (2)
O440.088 (3)0.104 (4)0.112 (5)−0.017 (3)0.040 (3)−0.057 (4)
O41A0.050 (2)0.093 (3)0.042 (2)−0.033 (2)0.0045 (18)−0.017 (2)
O42A0.048 (3)0.073 (4)0.054 (4)−0.015 (3)0.005 (2)0.011 (3)
O43A0.084 (3)0.093 (3)0.062 (3)−0.012 (2)0.001 (2)−0.002 (2)
O44A0.088 (3)0.104 (4)0.112 (5)−0.017 (3)0.040 (3)−0.057 (4)
N1A0.0401 (16)0.0467 (16)0.064 (2)−0.0047 (12)0.0047 (14)0.0039 (14)
N2A0.0340 (16)0.076 (2)0.062 (2)0.0107 (15)0.0091 (15)0.0117 (17)
N3A0.0545 (19)0.0522 (17)0.0420 (16)0.0164 (14)0.0032 (14)0.0018 (14)
C1A0.049 (2)0.049 (2)0.059 (2)−0.0084 (16)−0.0074 (18)0.0042 (17)
C2A0.055 (2)0.058 (2)0.070 (3)0.0147 (18)0.006 (2)−0.002 (2)
C3A0.051 (2)0.0427 (18)0.0352 (17)0.0103 (15)0.0029 (15)0.0094 (15)
C4A0.065 (3)0.075 (3)0.045 (2)0.021 (2)0.0090 (19)0.0111 (18)
C5A0.042 (2)0.083 (3)0.061 (2)0.013 (2)0.0187 (18)0.014 (2)
N1B0.040 (2)0.0394 (19)0.049 (2)0.0023 (19)−0.003 (2)0.0004 (16)
N2B0.036 (3)0.059 (3)0.080 (3)0.0010 (19)0.005 (2)0.008 (3)
N3B0.074 (4)0.052 (3)0.067 (2)0.024 (3)0.028 (2)0.012 (2)
C1B0.041 (3)0.051 (3)0.058 (3)0.003 (2)−0.002 (2)−0.006 (2)
C2B0.043 (3)0.052 (3)0.072 (3)0.005 (2)0.002 (2)−0.006 (2)
C3B0.040 (3)0.0350 (19)0.0348 (18)0.002 (2)−0.005 (3)0.0048 (15)
C4B0.060 (3)0.061 (3)0.042 (3)0.013 (2)0.008 (2)0.005 (2)
C5B0.045 (2)0.068 (5)0.062 (4)0.010 (3)0.017 (2)0.015 (4)
N1BA0.040 (2)0.0394 (19)0.049 (2)0.0023 (19)−0.003 (2)0.0004 (16)
N2BA0.036 (3)0.059 (3)0.080 (3)0.0010 (19)0.005 (2)0.008 (3)
N3BA0.074 (4)0.052 (3)0.067 (2)0.024 (3)0.028 (2)0.012 (2)
C1BA0.041 (3)0.051 (3)0.058 (3)0.003 (2)−0.002 (2)−0.006 (2)
C2BA0.043 (3)0.052 (3)0.072 (3)0.005 (2)0.002 (2)−0.006 (2)
C3BA0.040 (3)0.0350 (19)0.0348 (18)0.002 (2)−0.005 (3)0.0048 (15)
C4BA0.060 (3)0.061 (3)0.042 (3)0.013 (2)0.008 (2)0.005 (2)
C5BA0.045 (2)0.068 (5)0.062 (4)0.010 (3)0.017 (2)0.015 (4)
Geometric parameters (Å, º) top
Cl1—O131.422 (3)C5A—H5AA0.9900
Cl1—O121.430 (2)C5A—H5AB0.9900
Cl1—O141.439 (3)N1B—C2B1.297 (7)
Cl1—O111.442 (3)N1B—C3B1.367 (7)
Cl2—O231.404 (3)N1B—H1B0.8800
Cl2—O241.412 (3)N2B—C1B1.320 (8)
Cl2—O221.433 (4)N2B—C2B1.355 (7)
Cl2—O211.454 (4)N2B—H2B0.8800
Cl3—O341.402 (4)N3B—C5B1.460 (7)
Cl3—O34A1.417 (11)N3B—H3B10.9100
Cl3—O31A1.421 (12)N3B—H3B20.9100
Cl3—O32A1.425 (12)N3B—H3B30.9100
Cl3—O321.434 (5)C1B—C3B1.381 (8)
Cl3—O311.446 (5)C1B—H1BA0.9500
Cl3—O33A1.451 (11)C2B—H2BA0.9500
Cl3—O331.454 (5)C3B—C4B1.465 (7)
Cl4—O44A1.350 (11)C4B—C5B1.493 (10)
Cl4—O42A1.361 (10)C4B—H4BA0.9900
Cl4—O441.405 (6)C4B—H4BB0.9900
Cl4—O41A1.415 (8)C5B—H5BA0.9900
Cl4—O411.454 (5)C5B—H5BB0.9900
Cl4—O431.465 (5)N1BA—C2BA1.322 (13)
Cl4—O421.481 (5)N1BA—C3BA1.352 (13)
Cl4—O43A1.496 (9)N1BA—H1B10.8800
N1A—C2A1.305 (5)N2BA—C2BA1.321 (16)
N1A—C3A1.363 (4)N2BA—C1BA1.366 (15)
N1A—H1A0.8800N2BA—H2B10.8800
N2A—C2A1.298 (5)N3BA—C5BA1.457 (15)
N2A—C1A1.351 (5)N3BA—H3B40.9100
N2A—H2A0.8800N3BA—H3B50.9100
N3A—C5A1.481 (5)N3BA—H3B60.9100
N3A—H3A10.9100C1BA—C3BA1.360 (15)
N3A—H3A20.9100C1BA—H1BB0.9500
N3A—H3A30.9100C2BA—H2BB0.9500
C1A—C3A1.357 (5)C3BA—C4BA1.470 (13)
C1A—H1AA0.9500C4BA—C5BA1.483 (15)
C2A—H2AA0.9500C4BA—H4BC0.9900
C3A—C4A1.475 (5)C4BA—H4BD0.9900
C4A—C5A1.482 (6)C5BA—H5BC0.9900
C4A—H4AA0.9900C5BA—H5BD0.9900
C4A—H4AB0.9900
O13—Cl1—O12110.77 (19)H5AA—C5A—H5AB107.7
O13—Cl1—O14109.79 (18)C2B—N1B—C3B111.8 (5)
O12—Cl1—O14109.18 (17)C2B—N1B—H1B124.1
O13—Cl1—O11109.30 (16)C3B—N1B—H1B124.1
O12—Cl1—O11108.74 (16)C1B—N2B—C2B109.3 (5)
O14—Cl1—O11109.04 (19)C1B—N2B—H2B125.3
O23—Cl2—O24113.2 (3)C2B—N2B—H2B125.3
O23—Cl2—O22109.9 (2)C5B—N3B—H3B1109.5
O24—Cl2—O22110.6 (2)C5B—N3B—H3B2109.5
O23—Cl2—O21108.1 (2)H3B1—N3B—H3B2109.5
O24—Cl2—O21108.8 (2)C5B—N3B—H3B3109.5
O22—Cl2—O21105.9 (2)H3B1—N3B—H3B3109.5
O34A—Cl3—O31A109.3 (10)H3B2—N3B—H3B3109.5
O34A—Cl3—O32A107.0 (10)N2B—C1B—C3B108.5 (6)
O31A—Cl3—O32A110.8 (11)N2B—C1B—H1BA125.8
O34—Cl3—O32112.2 (3)C3B—C1B—H1BA125.8
O34—Cl3—O31112.0 (4)N1B—C2B—N2B106.6 (5)
O32—Cl3—O31105.7 (4)N1B—C2B—H2BA126.7
O34A—Cl3—O33A111.3 (7)N2B—C2B—H2BA126.7
O31A—Cl3—O33A108.1 (11)N1B—C3B—C1B103.7 (5)
O32A—Cl3—O33A110.4 (9)N1B—C3B—C4B124.5 (5)
O34—Cl3—O33110.7 (3)C1B—C3B—C4B131.7 (6)
O32—Cl3—O33106.6 (3)C3B—C4B—C5B115.3 (6)
O31—Cl3—O33109.3 (4)C3B—C4B—H4BA108.5
O44A—Cl4—O42A122.3 (10)C5B—C4B—H4BA108.5
O44A—Cl4—O41A119.9 (10)C3B—C4B—H4BB108.5
O42A—Cl4—O41A107.9 (7)C5B—C4B—H4BB108.5
O44—Cl4—O41103.5 (5)H4BA—C4B—H4BB107.5
O44—Cl4—O43134.2 (6)N3B—C5B—C4B114.8 (9)
O41—Cl4—O43101.5 (5)N3B—C5B—H5BA108.6
O44—Cl4—O42108.7 (4)C4B—C5B—H5BA108.6
O41—Cl4—O42102.1 (4)N3B—C5B—H5BB108.6
O43—Cl4—O42102.7 (4)C4B—C5B—H5BB108.6
O44A—Cl4—O43A107.3 (9)H5BA—C5B—H5BB107.6
O42A—Cl4—O43A112.8 (6)C2BA—N1BA—C3BA111.7 (11)
O41A—Cl4—O43A78.0 (6)C2BA—N1BA—H1B1124.1
C2A—N1A—C3A110.8 (3)C3BA—N1BA—H1B1124.1
C2A—N1A—H1A124.6C2BA—N2BA—C1BA105.3 (12)
C3A—N1A—H1A124.6C2BA—N2BA—H2B1127.3
C2A—N2A—C1A109.5 (3)C1BA—N2BA—H2B1127.3
C2A—N2A—H2A125.2C5BA—N3BA—H3B4109.5
C1A—N2A—H2A125.2C5BA—N3BA—H3B5109.5
C5A—N3A—H3A1109.5H3B4—N3BA—H3B5109.5
C5A—N3A—H3A2109.5C5BA—N3BA—H3B6109.5
H3A1—N3A—H3A2109.5H3B4—N3BA—H3B6109.5
C5A—N3A—H3A3109.5H3B5—N3BA—H3B6109.5
H3A1—N3A—H3A3109.5C3BA—C1BA—N2BA111.5 (13)
H3A2—N3A—H3A3109.5C3BA—C1BA—H1BB124.3
N2A—C1A—C3A107.6 (3)N2BA—C1BA—H1BB124.3
N2A—C1A—H1AA126.2N2BA—C2BA—N1BA109.0 (12)
C3A—C1A—H1AA126.2N2BA—C2BA—H2BB125.5
N2A—C2A—N1A107.8 (4)N1BA—C2BA—H2BB125.5
N2A—C2A—H2AA126.1N1BA—C3BA—C1BA102.3 (11)
N1A—C2A—H2AA126.1N1BA—C3BA—C4BA130.5 (14)
C1A—C3A—N1A104.3 (3)C1BA—C3BA—C4BA127.2 (14)
C1A—C3A—C4A130.6 (4)C3BA—C4BA—C5BA116.3 (15)
N1A—C3A—C4A125.1 (4)C3BA—C4BA—H4BC108.2
C3A—C4A—C5A115.8 (4)C5BA—C4BA—H4BC108.2
C3A—C4A—H4AA108.3C3BA—C4BA—H4BD108.2
C5A—C4A—H4AA108.3C5BA—C4BA—H4BD108.2
C3A—C4A—H4AB108.3H4BC—C4BA—H4BD107.4
C5A—C4A—H4AB108.3N3BA—C5BA—C4BA119 (2)
H4AA—C4A—H4AB107.4N3BA—C5BA—H5BC107.6
N3A—C5A—C4A113.8 (3)C4BA—C5BA—H5BC107.6
N3A—C5A—H5AA108.8N3BA—C5BA—H5BD107.6
C4A—C5A—H5AA108.8C4BA—C5BA—H5BD107.6
N3A—C5A—H5AB108.8H5BC—C5BA—H5BD107.0
C4A—C5A—H5AB108.8
C2A—N2A—C1A—C3A−0.3 (5)N2B—C1B—C3B—N1B−0.6 (10)
C1A—N2A—C2A—N1A0.3 (5)N2B—C1B—C3B—C4B−179.0 (8)
C3A—N1A—C2A—N2A−0.1 (5)N1B—C3B—C4B—C5B60.4 (11)
N2A—C1A—C3A—N1A0.3 (4)C1B—C3B—C4B—C5B−121.6 (10)
N2A—C1A—C3A—C4A179.0 (4)C3B—C4B—C5B—N3B58.8 (9)
C2A—N1A—C3A—C1A−0.1 (4)C2BA—N2BA—C1BA—C3BA−2 (4)
C2A—N1A—C3A—C4A−178.9 (4)C1BA—N2BA—C2BA—N1BA−2 (3)
C1A—C3A—C4A—C5A118.7 (5)C3BA—N1BA—C2BA—N2BA4 (2)
N1A—C3A—C4A—C5A−62.9 (5)C2BA—N1BA—C3BA—C1BA−5 (3)
C3A—C4A—C5A—N3A−64.0 (5)C2BA—N1BA—C3BA—C4BA174 (2)
C2B—N2B—C1B—C3B0.9 (9)N2BA—C1BA—C3BA—N1BA4 (3)
C3B—N1B—C2B—N2B0.3 (9)N2BA—C1BA—C3BA—C4BA−175 (2)
C1B—N2B—C2B—N1B−0.7 (8)N1BA—C3BA—C4BA—C5BA−42 (3)
C2B—N1B—C3B—C1B0.2 (10)C1BA—C3BA—C4BA—C5BA137 (3)
C2B—N1B—C3B—C4B178.7 (7)C3BA—C4BA—C5BA—N3BA−50 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O13i0.882.503.337 (4)160
N1A—H1A···O14i0.882.493.052 (4)122
N1A—H1A···O43ii0.882.473.021 (7)121
N1A—H1A···O41Aii0.882.362.978 (9)127
N2A—H2A···Cl40.882.963.709 (3)145
N2A—H2A···O410.882.032.907 (9)171
N2A—H2A···O44A0.882.082.95 (2)168
N3A—H3A1···O21iii0.912.563.040 (4)114
N3A—H3A1···O34iv0.912.233.065 (6)153
N3A—H3A1···O33Aiv0.912.112.861 (12)139
N3A—H3A2···Cl1v0.912.983.742 (3)143
N3A—H3A2···O11v0.912.453.031 (4)122
N3A—H3A2···O12v0.912.443.232 (4)146
N3A—H3A2···O42v0.912.533.207 (8)131
N3A—H3A2···O42Av0.912.573.272 (14)134
N3A—H3A3···Cl30.912.953.735 (3)145
N3A—H3A3···O310.912.513.055 (8)119
N3A—H3A3···O320.912.263.120 (8)159
N3A—H3A3···O32A0.912.143.04 (2)170
C2A—H2AA···O14i0.952.653.129 (5)112
C2A—H2AA···O220.952.403.074 (5)128
C4A—H4AB···O43ii0.992.663.379 (8)129
C5A—H5AA···O42v0.992.703.158 (9)109
C5A—H5AA···O43v0.992.703.310 (7)120
C5A—H5AB···O12vi0.992.613.542 (5)158
N1B—H1B···Cl10.882.913.714 (5)153
N1B—H1B···O120.882.393.265 (6)171
N1B—H1B···O140.882.382.961 (6)124
N2B—H2B···O320.882.102.939 (9)159
N3B—H3B1···Cl40.912.943.695 (14)142
N3B—H3B1···O410.912.052.937 (19)163
N3B—H3B1···O420.912.653.168 (13)117
N3B—H3B2···O11vii0.912.563.120 (14)120
N3B—H3B2···O13vii0.912.453.269 (11)150
N3B—H3B2···O31viii0.912.633.310 (14)132
N3B—H3B3···O210.912.362.910 (10)119
N3B—H3B3···O34ix0.912.563.374 (13)150
C1B—H1BA···O24ix0.952.643.441 (7)142
C2B—H2BA···O22iii0.952.503.024 (6)115
C4B—H4BB···O33ix0.992.503.433 (8)156
C5B—H5BA···O11x0.992.523.249 (10)130
N2BA—H2B1···O22iii0.882.383.150 (15)146
N3BA—H3B4···Cl1vii0.912.783.62 (3)155
N3BA—H3B4···O11vii0.912.152.93 (4)144
N3BA—H3B4···O13vii0.912.403.12 (3)137
N3BA—H3B4···O31Aviii0.912.593.14 (4)120
N3BA—H3B5···Cl20.912.823.66 (3)154
N3BA—H3B5···O210.912.132.83 (2)133
N3BA—H3B5···O240.912.483.29 (4)149
N3BA—H3B6···Cl40.912.873.77 (4)168
N3BA—H3B6···O44A0.912.283.07 (5)146
C1BA—H1BB···O140.952.163.103 (17)171
C2BA—H2BB···Cl30.952.753.644 (14)157
C2BA—H2BB···O32A0.952.463.12 (3)127
C2BA—H2BB···O34A0.952.093.04 (2)173
C4BA—H4BD···O11x0.992.563.250 (13)127
C4BA—H4BC···O120.992.383.325 (16)159
C5BA—H5BC···Cl3ix0.992.983.86 (3)149
C5BA—H5BC···O34Aix0.992.263.18 (4)153
C5BA—H5BD···O31Aviii0.992.573.22 (4)123
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+1/2; (iv) x, −y+3/2, z+1/2; (v) x−1, y, z; (vi) x−1, −y+3/2, z+1/2; (vii) −x+2, y−1/2, −z+1/2; (viii) x+1, y, z; (ix) −x+1, −y+1, −z; (x) x, −y+3/2, z−1/2.
 

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer. RJB wishes to acknowledge the NSF Grant 1205608 `Partnership for Reduced Dimensional Materials' for partial funding of this work.

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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.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 9| September 2016| x161481
doi:10.1107/S2414314616014814
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