3,4,6-Tri­amino-N-phenyl­thieno[2,3-b]pyridine-2-carboxamide

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Hussein, B.R.M.; Albayati, M.R.

doi:10.1107/S1600536814013981

organic compounds

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ISSN: 2056-9890

Volume 70| Part 7| July 2014| Page o805

https://doi.org/10.1107/S1600536814013981

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3,4,6-Triamino-N-phenylthieno[2,3-b]pyridine-2-carboxamide

Shaaban K. Mohamed,^a,^b Joel T. Mague,^c Mehmet Akkurt,^d Bahgat R. M. Hussein ^e and Mustafa R. Albayati ^f ^*

^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, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 27 May 2014; accepted 14 June 2014; online 25 June 2014)

In the title compound, C₁₄H₁₃N₅OS, the dihedral angle between the fused ring system (r.m.s. deviation = 0.028 Å) and the phenyl ring is 48.24 (4)°. The molecule features both an intramolecular N—H⋯O and an N—H⋯N hydrogen bond. In the crystal, molecules are linked by N—H⋯O and N—H⋯N hydrogen bonds, generating a three-dimensional network. A weak N—H⋯π interaction is also observed.

Keywords: crystal structure.

CCDC reference: 1008299

Related literature

For background to thienopyridine-containing compounds, see: Boschelli et al. (2008 ); Bakhite et al. (2002 ); Schnute et al. (2007 ).

Experimental

Crystal data

C₁₄H₁₃N₅OS
M_r = 299.36
Monoclinic, P 2₁ /n
a = 5.2732 (7) Å
b = 21.028 (3) Å
c = 11.9777 (16) Å
β = 93.969 (2)°
V = 1325.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 150 K
0.21 × 0.13 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.85, T_max = 0.98
24103 measured reflections
3500 independent reflections
3017 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.101
S = 1.06
3500 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C9–C14 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N4ⁱ	0.91	2.52	3.2226 (17)	134
N3—H3A⋯N1ⁱⁱ	0.91	2.07	2.9398 (17)	161
N3—H3B⋯N4	0.91	2.38	2.9802 (17)	124
N3—H3B⋯N2ⁱⁱⁱ	0.91	2.41	3.2034 (16)	146
N4—H4B⋯O1	0.91	2.15	2.8387 (16)	132
N4—H4B⋯O1^iv	0.91	2.32	2.9991 (16)	132
N2—H2B⋯Cg3^v	0.91	2.56	3.4662 (14)	173
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1; (v) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXT (Bruker, 2013); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 1008299

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536814013981/hb7235sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013981/hb7235Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013981/hb7235Isup3.cml

checkCIF report

Comment top

Thienopyridines and their analogs are an interesting class of molecules due to their extensive spectrum of pharmacological properties, for example anti-inflammatory (Boschelli et al., 2008), anti-microbial (Bakhite et al., 2002) and anti-viral (Schnute et al., 2007) activities. As part of our program in the development of new heterocyclic molecules with potential bioactivities, we report in this study the synthesis and crystal structure determination of the title compound.

In the title compound, the fused ring system is nearly planar with an r.m.s. deviation of 0.028 Å and makes a dihedral angle of 48.24 (4)° with the terminal phenyl group. The conformation of the carboxamide group is partially determined by the intramolecular N4—H4B···O1 hydrogen bond (Fig. 1 and Table 1). In the solid, the molecules associate through pairwise intermolecular N4—H4B···O1 and single N3—H3a···N1 hydrogen bonds to form a three-dimensional network (Figs. 2 and 3 and Table 1). A weak N—H···π interaction is observed between the NH₂ group (N2—H2B) and the centroid of the C9–C14 phenyl ring.

Related literature top

For background to thienopyridine-containing compounds, see: Boschelli et al. (2008); Bakhite et al. (2002); Schnute et al. (2007).

Experimental top

A mixture of 2.7 mmol (500 mg) of 4,6-diamino-2-mercaptonicotinonitrile, 2.7 mmol (150 mg) potassium hydroxide and 1.86 mmol (320 mg) in 30 ml e thanol was stirred and refluxed for 3 h. The excess solvent was evaporated under vacuum and the resulting solid product was filtered off, washed with cold ethanol and recrystallized from ethanol to furnish colourless crystals (730 mg; 87% yield). Mp. 531 – 533 K.

IR (ν_max, cm^-1): 3462, 3402, 3352, (3NH₂), 3213 (NH), 1645 (C=O), 1614 (C=N); ¹HNMR (DMSO-d₆), δ, p.p.m.: 8.88 (s, 1H, NH exchanged by D₂O), 7.65–7.63 (d, J = 8 Hz, 2H, arom), 7.29–7.25 (t, J = 8 Hz, 2H, arom), 7.02–6.99 (m,, 3H, arom+ NH₂ exchanged by D₂O), 6.11 (s, 2H, NH₂ exchanged by D₂O), 6.02 (s, 2H, NH₂ exchanged by D₂O), 5.59 (s, 1H, CH pyridyl).

Structure description top

For background to thienopyridine-containing compounds, see: Boschelli et al. (2008); Bakhite et al. (2002); Schnute et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Bruker, 2013); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The title compound with 50% probability ellipsoids and with intramolecular hydrogen bonds shown as dotted lines.
	Fig. 2. Packing viewed down the a axis showing a portion of the zigzag sheet with the intermolecular hydrogen bonds depicted by dotted lines.
	Fig. 3. Packing viewed parallel to (101).

3,4,6-Triamino-N-phenylthieno[2,3-b]pyridine-2-carboxamide top

Crystal data top

C₁₄H₁₃N₅OS	F(000) = 624
M_r = 299.36	D_x = 1.501 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9996 reflections
a = 5.2732 (7) Å	θ = 2.6–29.1°
b = 21.028 (3) Å	µ = 0.25 mm⁻¹
c = 11.9777 (16) Å	T = 150 K
β = 93.969 (2)°	Block, colourless
V = 1325.0 (3) Å³	0.21 × 0.13 × 0.09 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3500 independent reflections
Radiation source: fine-focus sealed tube	3017 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 8.3660 pixels mm^-1	θ_max = 29.1°, θ_min = 1.9°
φ and ω scans	h = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −28→28
T_min = 0.85, T_max = 0.98	l = −16→16
24103 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0512P)² + 0.5972P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3500 reflections	Δρ_max = 0.42 e Å⁻³
190 parameters	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₄H₁₃N₅OS	V = 1325.0 (3) Å³
M_r = 299.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.2732 (7) Å	µ = 0.25 mm⁻¹
b = 21.028 (3) Å	T = 150 K
c = 11.9777 (16) Å	0.21 × 0.13 × 0.09 mm
β = 93.969 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3500 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	3017 reflections with I > 2σ(I)
T_min = 0.85, T_max = 0.98	R_int = 0.046
24103 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.06	Δρ_max = 0.42 e Å⁻³
3500 reflections	Δρ_min = −0.25 e Å⁻³
190 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
S1	0.40493 (6)	0.35471 (2)	0.83539 (3)	0.0168 (1)
O1	0.6615 (2)	0.47538 (5)	0.61593 (8)	0.0249 (3)
N1	0.0339 (2)	0.26672 (5)	0.82888 (9)	0.0169 (3)
N2	−0.2636 (2)	0.18599 (6)	0.82055 (10)	0.0230 (3)
N3	−0.1968 (2)	0.31627 (6)	0.49527 (10)	0.0220 (3)
N4	0.2168 (2)	0.41258 (6)	0.52579 (9)	0.0209 (3)
N5	0.7313 (2)	0.47187 (6)	0.80636 (10)	0.0196 (3)
C1	−0.1541 (3)	0.23617 (6)	0.76882 (11)	0.0168 (3)
C2	−0.2385 (3)	0.25273 (6)	0.65898 (11)	0.0170 (3)
C3	−0.1212 (3)	0.30131 (6)	0.60362 (11)	0.0161 (3)
C4	0.0807 (2)	0.33451 (6)	0.66470 (10)	0.0150 (3)
C5	0.1430 (2)	0.31391 (6)	0.77427 (10)	0.0149 (3)
C6	0.2455 (3)	0.38441 (6)	0.63091 (11)	0.0157 (3)
C7	0.4308 (3)	0.40001 (6)	0.71359 (10)	0.0163 (3)
C8	0.6148 (3)	0.45111 (6)	0.70611 (11)	0.0172 (3)
C9	0.9058 (3)	0.52266 (6)	0.82104 (11)	0.0178 (3)
C10	1.0866 (3)	0.53587 (7)	0.74444 (12)	0.0199 (4)
C11	1.2629 (3)	0.58416 (7)	0.76735 (14)	0.0245 (4)
C12	1.2616 (3)	0.61978 (7)	0.86512 (14)	0.0261 (4)
C13	1.0791 (3)	0.60708 (7)	0.94063 (13)	0.0236 (4)
C14	0.9013 (3)	0.55895 (7)	0.91876 (12)	0.0207 (4)
H2	−0.37710	0.23050	0.62220	0.0200*
H2A	−0.17740	0.16940	0.88230	0.0280*
H2B	−0.36030	0.15820	0.77790	0.0280*
H3A	−0.29050	0.28560	0.45810	0.0260*
H3B	−0.07270	0.33330	0.45530	0.0260*
H4A	0.05280	0.42370	0.50670	0.0250*
H4B	0.33410	0.44320	0.51430	0.0250*
H5A	0.66340	0.45840	0.87010	0.0230*
H10	1.08930	0.51200	0.67710	0.0240*
H11	1.38620	0.59300	0.71530	0.0290*
H12	1.38390	0.65240	0.88020	0.0310*
H13	1.07580	0.63140	1.00740	0.0280*
H14	0.77650	0.55070	0.97040	0.0250*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0174 (2)	0.0186 (2)	0.0138 (2)	−0.0032 (1)	−0.0034 (1)	0.0018 (1)
O1	0.0273 (6)	0.0270 (5)	0.0196 (5)	−0.0099 (4)	−0.0033 (4)	0.0059 (4)
N1	0.0165 (6)	0.0174 (5)	0.0167 (5)	−0.0011 (4)	0.0000 (4)	0.0018 (4)
N2	0.0234 (6)	0.0229 (6)	0.0223 (6)	−0.0066 (5)	−0.0008 (5)	0.0051 (5)
N3	0.0243 (6)	0.0263 (6)	0.0147 (5)	−0.0084 (5)	−0.0037 (4)	0.0006 (5)
N4	0.0256 (6)	0.0215 (6)	0.0151 (5)	−0.0059 (5)	−0.0027 (5)	0.0044 (4)
N5	0.0211 (6)	0.0193 (6)	0.0180 (5)	−0.0064 (4)	−0.0012 (4)	0.0003 (4)
C1	0.0152 (6)	0.0166 (6)	0.0187 (6)	0.0005 (5)	0.0028 (5)	−0.0001 (5)
C2	0.0155 (6)	0.0177 (6)	0.0175 (6)	−0.0021 (5)	−0.0001 (5)	−0.0016 (5)
C3	0.0162 (6)	0.0173 (6)	0.0145 (6)	0.0001 (5)	−0.0003 (5)	−0.0015 (5)
C4	0.0168 (6)	0.0149 (6)	0.0131 (6)	−0.0007 (5)	−0.0006 (5)	−0.0002 (4)
C5	0.0141 (6)	0.0156 (6)	0.0145 (6)	−0.0001 (4)	−0.0016 (5)	−0.0011 (4)
C6	0.0178 (6)	0.0151 (6)	0.0140 (5)	−0.0009 (5)	0.0003 (5)	−0.0005 (4)
C7	0.0181 (6)	0.0163 (6)	0.0142 (6)	−0.0020 (5)	−0.0004 (5)	0.0019 (5)
C8	0.0160 (6)	0.0165 (6)	0.0188 (6)	−0.0012 (5)	−0.0018 (5)	0.0004 (5)
C9	0.0162 (6)	0.0147 (6)	0.0218 (6)	−0.0004 (5)	−0.0044 (5)	0.0019 (5)
C10	0.0169 (6)	0.0184 (6)	0.0242 (7)	0.0010 (5)	−0.0008 (5)	0.0001 (5)
C11	0.0158 (7)	0.0237 (7)	0.0338 (8)	−0.0020 (5)	−0.0003 (6)	0.0045 (6)
C12	0.0206 (7)	0.0187 (7)	0.0375 (8)	−0.0043 (5)	−0.0079 (6)	0.0019 (6)
C13	0.0246 (7)	0.0184 (7)	0.0264 (7)	−0.0003 (5)	−0.0081 (6)	−0.0020 (5)
C14	0.0201 (7)	0.0200 (6)	0.0214 (6)	−0.0009 (5)	−0.0030 (5)	0.0000 (5)

Geometric parameters (Å, º) top

S1—C5	1.7435 (12)	C2—C3	1.3866 (19)
S1—C7	1.7555 (13)	C3—C4	1.4312 (19)
O1—C8	1.2348 (17)	C4—C6	1.4383 (18)
N1—C1	1.3470 (18)	C4—C5	1.3994 (17)
N1—C5	1.3400 (16)	C6—C7	1.382 (2)
N2—C1	1.3712 (18)	C7—C8	1.455 (2)
N3—C3	1.3677 (18)	C9—C10	1.396 (2)
N4—C6	1.3902 (17)	C9—C14	1.399 (2)
N5—C8	1.3812 (18)	C10—C11	1.391 (2)
N5—C9	1.4128 (18)	C11—C12	1.391 (2)
N2—H2B	0.9100	C12—C13	1.391 (2)
N2—H2A	0.9100	C13—C14	1.392 (2)
N3—H3B	0.9100	C2—H2	0.9500
N3—H3A	0.9100	C10—H10	0.9500
N4—H4A	0.9100	C11—H11	0.9500
N4—H4B	0.9100	C12—H12	0.9500
N5—H5A	0.9100	C13—H13	0.9500
C1—C2	1.4033 (19)	C14—H14	0.9500

C5—S1—C7	91.32 (6)	N4—C6—C7	125.12 (13)
C1—N1—C5	114.68 (11)	C4—C6—C7	112.50 (11)
C8—N5—C9	126.43 (12)	C6—C7—C8	124.95 (12)
C1—N2—H2B	119.00	S1—C7—C6	112.03 (10)
H2A—N2—H2B	116.00	S1—C7—C8	122.86 (10)
C1—N2—H2A	117.00	O1—C8—N5	121.75 (13)
C3—N3—H3B	115.00	O1—C8—C7	122.24 (12)
H3A—N3—H3B	114.00	N5—C8—C7	116.00 (11)
C3—N3—H3A	114.00	C10—C9—C14	119.56 (13)
C6—N4—H4B	114.00	N5—C9—C10	122.49 (12)
H4A—N4—H4B	115.00	N5—C9—C14	117.90 (13)
C6—N4—H4A	112.00	C9—C10—C11	119.54 (13)
C9—N5—H5A	115.00	C10—C11—C12	121.14 (15)
C8—N5—H5A	117.00	C11—C12—C13	119.21 (14)
N1—C1—C2	123.80 (12)	C12—C13—C14	120.29 (14)
N2—C1—C2	119.90 (13)	C9—C14—C13	120.26 (14)
N1—C1—N2	116.30 (12)	C1—C2—H2	120.00
C1—C2—C3	120.54 (13)	C3—C2—H2	120.00
N3—C3—C4	122.04 (12)	C9—C10—H10	120.00
N3—C3—C2	120.86 (13)	C11—C10—H10	120.00
C2—C3—C4	117.10 (12)	C10—C11—H11	119.00
C5—C4—C6	112.49 (11)	C12—C11—H11	119.00
C3—C4—C6	130.89 (12)	C11—C12—H12	120.00
C3—C4—C5	116.52 (11)	C13—C12—H12	120.00
S1—C5—C4	111.67 (9)	C12—C13—H13	120.00
N1—C5—C4	127.31 (11)	C14—C13—H13	120.00
S1—C5—N1	120.92 (9)	C9—C14—H14	120.00
N4—C6—C4	122.39 (12)	C13—C14—H14	120.00

C7—S1—C5—N1	176.86 (11)	C6—C4—C5—S1	−0.75 (14)
C7—S1—C5—C4	0.24 (10)	C6—C4—C5—N1	−177.10 (12)
C5—S1—C7—C6	0.35 (11)	C3—C4—C6—N4	4.6 (2)
C5—S1—C7—C8	175.81 (12)	C3—C4—C6—C7	−175.08 (13)
C5—N1—C1—N2	177.57 (11)	C5—C4—C6—N4	−179.26 (12)
C5—N1—C1—C2	−1.99 (19)	C5—C4—C6—C7	1.02 (16)
C1—N1—C5—S1	−175.21 (10)	N4—C6—C7—S1	179.46 (11)
C1—N1—C5—C4	0.84 (18)	N4—C6—C7—C8	4.1 (2)
C9—N5—C8—O1	2.2 (2)	C4—C6—C7—S1	−0.83 (15)
C9—N5—C8—C7	−176.62 (13)	C4—C6—C7—C8	−176.18 (13)
C8—N5—C9—C10	−36.6 (2)	S1—C7—C8—O1	167.43 (11)
C8—N5—C9—C14	146.03 (14)	S1—C7—C8—N5	−13.78 (18)
N1—C1—C2—C3	2.8 (2)	C6—C7—C8—O1	−17.7 (2)
N2—C1—C2—C3	−176.78 (13)	C6—C7—C8—N5	161.09 (14)
C1—C2—C3—N3	177.76 (13)	N5—C9—C10—C11	−176.08 (14)
C1—C2—C3—C4	−2.1 (2)	C14—C9—C10—C11	1.2 (2)
N3—C3—C4—C5	−178.88 (12)	N5—C9—C14—C13	176.12 (13)
N3—C3—C4—C6	−2.9 (2)	C10—C9—C14—C13	−1.3 (2)
C2—C3—C4—C5	1.00 (18)	C9—C10—C11—C12	−0.3 (2)
C2—C3—C4—C6	176.98 (14)	C10—C11—C12—C13	−0.6 (2)
C3—C4—C5—S1	175.96 (9)	C11—C12—C13—C14	0.5 (2)
C3—C4—C5—N1	−0.39 (19)	C12—C13—C14—C9	0.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C9–C14 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N4ⁱ	0.91	2.52	3.2226 (17)	134
N3—H3A···N1ⁱⁱ	0.91	2.07	2.9398 (17)	161
N3—H3B···N4	0.91	2.38	2.9802 (17)	124
N3—H3B···N2ⁱⁱⁱ	0.91	2.41	3.2034 (16)	146
N4—H4B···O1	0.91	2.15	2.8387 (16)	132
N4—H4B···O1^iv	0.91	2.32	2.9991 (16)	132
N2—H2B···Cg3^v	0.91	2.56	3.4662 (14)	173

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

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C9–C14 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N4ⁱ	0.91	2.52	3.2226 (17)	134
N3—H3A···N1ⁱⁱ	0.91	2.07	2.9398 (17)	161
N3—H3B···N4	0.91	2.38	2.9802 (17)	124
N3—H3B···N2ⁱⁱⁱ	0.91	2.41	3.2034 (16)	146
N4—H4B···O1	0.91	2.15	2.8387 (16)	132
N4—H4B···O1^iv	0.91	2.32	2.9991 (16)	132
N2—H2B···Cg3^v	0.91	2.56	3.4662 (14)	173

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

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

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