N,N-Dimethyl-1H-pyrazolo­[3,4-d]pyrimidin-4-amine monohydrate

El Hafi, M.; Boulhaoua, M.; Lahmidi, S.; Ramli, Y.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314618002432

organic compounds

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ISSN: 2414-3146

Volume 3| Part 2| February 2018| x180243

https://doi.org/10.1107/S2414314618002432

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N,N-Dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine monohydrate

Mohamed El Hafi,^a ^* Mohammed Boulhaoua,^a Sanae Lahmidi,^a Youssef Ramli,^b El Mokhtar Essassi ^a and Joel T. Mague ^c

^aLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche Des Sciences des Médicaments, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^bLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V, University Rabat, Morocco, and ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: elhafi.mohamed1@gmail.com

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 8 February 2018; accepted 9 February 2018; online 23 February 2018)

The asymmetric unit of the title compound, C₇H₉N₅·H₂O, consists of two formula units differing slightly in the orientation of the dimethylamino groups. In the crystal, a combination of O—H⋯N and N—H⋯O hydrogen bonds involving the water molecules of crystallization, as well as slipped π-stacking interactions between pyrazolopyrimidine units form layers parallel to the bc plane.

Keywords: crystal structure; hydrogen bond; π-stacking; pyrazolopyrimidine.

CCDC reference: 1823202

Structure description

Pyrazolo[3,4-d]pyrimidines display a broad spectrum of biological activity including antiviral, antitubercular (Trivedi et al., 2012 ) and antibacterial agents (Bondock et al., 2008 ). The present work is a continuation of the investigation of pyrazolo[3,4-d]pyrimidine derivatives reported by our team (El Hafi et al., 2017 ).

The asymmetric unit consists of two independent molecules and two water molecules of crystallization (Fig. 1). The main molecules differ primarily in the orientation of the dimethylamino substituent. Thus, the C2—C1—N5—C6 torsion angle is −6.3 (2)° while the C9—C8—N10—C14 torsion angle is 5.4 (2)°. The bicyclic moieties are slightly twisted, as seen from the dihedral angles of 1.99 (9) and 1.56 (9)° between the five- and six-membered rings.

Figure 1
The asymmetric unit with labeling scheme and 50% probability displacement ellipsoids.

In the crystal, head-to-tail, slipped π-stacking interactions between the five- and six-membered rings of the N1-containing molecule with those in the N5-containing molecule form dimers with a centroid–centroid distance of 3.543 (1) Å for the N1/N2/C4/C2/C3 ring and the N8/C11/C9/C8/N9/C12 ring at x, y − 1, z, while for the N3/C4/C2/C1/N4/C5 and N6/N7/C11/C9/C10 rings the corresponding distance is 3.750 (1) Å. The dimers are connected into chains parallel to the b-axis direction by N2—H2⋯O1 and O1—H1A—N8 hydrogen bonds (Table 1). In the center of Fig. 2 are two dimers connected by hydrogen bonding to the water molecules of crystallization and representing a portion of one chain. The chains are elaborated into layers parallel to the bc plane by O2—H2A—N9 and O1—H1B—N4 hydrogen bonds (Table 1 and Figs. 2 and 3). In the layers, the mean planes of the bicyclic moieties in adjacent chains are inclined to one another by 30.1 (1)°.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.94 (2)	1.82 (2)	2.7546 (18)	173 (2)
N7—H7⋯O2ⁱⁱ	0.99 (2)	1.74 (2)	2.7256 (19)	179 (3)
O1—H1A⋯N8ⁱ	0.93 (3)	1.94 (3)	2.8607 (19)	172 (2)
O1—H1B⋯N4ⁱⁱⁱ	0.88 (3)	1.95 (3)	2.8158 (18)	170 (2)
O2—H2A⋯N9^iv	0.97 (3)	1.86 (3)	2.8042 (18)	166 (2)
O2—H2B⋯N3ⁱⁱ	0.89 (3)	1.98 (3)	2.865 (2)	173 (2)
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Plan view of a portion of one layer showing the O—H⋯N and N—H⋯O hydrogen bonds (red and blue dashed lines, respectively) and the π-stacking interactions (tan dashed lines) projected along the a-axis direction.

Figure 3
View of the layer structure projected along the b-axis direction. Intermolecular interactions are depicted as in Fig. 2

Synthesis and crystallization

To a solution of 1H-pyrazolo[3,4-d]pyrimidine-4-thione (0.5 g, 3.3 mmol) in DMF (15 ml) was added a catalytic amount of tetra-n-butylammonium bromide and potassium carbonate (0.54 g, 3.96 mmol). The mixture was heated to reflux for 12 h. The solution was filtered and the solvent removed under reduced pressure. The resulting residue was purified by column chromatography (EtOAc/hexane 8/2). The title compound was recrystallized from ethanol solution, at room temperature, giving colorless crystals (yield: 40%; m.p. 371–373 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₇H₉N₅·H₂O
M_r	181.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	14.5177 (5), 8.3622 (3), 14.9892 (6)
β (°)	110.724 (2)
V (Å³)	1701.95 (11)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.85
Crystal size (mm)	0.13 × 0.12 × 0.09

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.75, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	12386, 3309, 2718
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.122, 1.04
No. of reflections	3309
No. of parameters	312
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1823202

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618002432/vm4033sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618002432/vm4033Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618002432/vm4033Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314618002432/vm4033Isup4.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 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

N,N-Dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine monohydrate top

Crystal data top

C₇H₉N₅·H₂O	F(000) = 768
M_r = 181.21	D_x = 1.414 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 14.5177 (5) Å	Cell parameters from 8628 reflections
b = 8.3622 (3) Å	θ = 6.0–72.4°
c = 14.9892 (6) Å	µ = 0.85 mm⁻¹
β = 110.724 (2)°	T = 150 K
V = 1701.95 (11) Å³	Plate, colourless
Z = 8	0.13 × 0.12 × 0.09 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3309 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2718 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.4°, θ_min = 3.3°
ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −10→10
T_min = 0.75, T_max = 0.93	l = −18→17
12386 measured reflections

Refinement top

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)] = 0.044	Hydrogen site location: mixed
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0654P)² + 0.6351P] where P = (F_o² + 2F_c²)/3
3309 reflections	(Δ/σ)_max < 0.001
312 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.25 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.

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. Independent refinement of the H-atoms of the C13 methyl group gave an unacceptible geometry so these were included as riding contributions in calculated positions.

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

	x	y	z	U_iso*/U_eq
N1	0.35991 (10)	−0.08305 (16)	0.59163 (10)	0.0250 (3)
N2	0.34162 (10)	−0.20751 (15)	0.52829 (9)	0.0221 (3)
H2	0.3287 (17)	−0.309 (3)	0.5484 (16)	0.045 (6)*
N3	0.33702 (10)	−0.25750 (15)	0.36887 (9)	0.0236 (3)
N4	0.37264 (10)	−0.02269 (15)	0.29363 (9)	0.0220 (3)
N5	0.40567 (10)	0.22662 (15)	0.36469 (9)	0.0232 (3)
C1	0.38315 (11)	0.07230 (17)	0.36999 (11)	0.0191 (3)
C2	0.37115 (11)	0.00241 (17)	0.45202 (11)	0.0190 (3)
C3	0.37741 (12)	0.04219 (18)	0.54641 (11)	0.0223 (3)
H3	0.3931 (14)	0.145 (2)	0.5792 (14)	0.029 (5)*
C4	0.34815 (11)	−0.16102 (17)	0.44479 (11)	0.0194 (3)
C5	0.35117 (12)	−0.17807 (17)	0.29836 (11)	0.0231 (3)
H5	0.3459 (14)	−0.246 (2)	0.2426 (14)	0.028 (5)*
N6	0.11735 (12)	1.09738 (17)	0.29206 (10)	0.0315 (3)
C6	0.40961 (14)	0.33787 (18)	0.44047 (13)	0.0270 (4)
H6A	0.4672 (17)	0.321 (3)	0.4968 (16)	0.040 (6)*
H6B	0.3490 (16)	0.327 (2)	0.4575 (15)	0.034 (5)*
H6C	0.4086 (16)	0.446 (3)	0.4144 (15)	0.041 (6)*
C7	0.42515 (15)	0.2901 (2)	0.28240 (13)	0.0313 (4)
H7A	0.364 (2)	0.329 (3)	0.233 (2)	0.067 (8)*
H7B	0.4553 (16)	0.205 (3)	0.2542 (15)	0.045 (6)*
H7C	0.470 (2)	0.378 (3)	0.3036 (19)	0.063 (7)*
N7	0.14486 (10)	1.21815 (16)	0.35787 (10)	0.0257 (3)
H7	0.1599 (15)	1.323 (3)	0.3362 (15)	0.037 (5)*
N8	0.16768 (10)	1.26041 (15)	0.52296 (10)	0.0237 (3)
N9	0.13523 (9)	1.02412 (15)	0.59898 (9)	0.0214 (3)
N10	0.09608 (10)	0.77770 (15)	0.52618 (10)	0.0239 (3)
C8	0.11589 (11)	0.93300 (17)	0.51981 (11)	0.0195 (3)
C9	0.11820 (11)	1.00684 (17)	0.43506 (11)	0.0213 (3)
C10	0.10148 (13)	0.9713 (2)	0.33780 (12)	0.0285 (4)
H10	0.0784 (16)	0.867 (3)	0.3032 (16)	0.041 (6)*
C11	0.14572 (11)	1.16857 (17)	0.44357 (11)	0.0208 (3)
C13	0.09545 (14)	0.7092 (2)	0.61547 (12)	0.0305 (4)
H13A	0.163244	0.687890	0.657711	0.046*
H13B	0.058005	0.609046	0.602261	0.046*
H13C	0.064677	0.784759	0.646418	0.046*
C14	0.08358 (14)	0.66887 (19)	0.44671 (13)	0.0288 (4)
H14A	0.0172 (17)	0.687 (3)	0.3924 (16)	0.043 (6)*
H14B	0.0928 (19)	0.560 (3)	0.4751 (18)	0.057 (7)*
H14C	0.1366 (17)	0.686 (3)	0.4205 (16)	0.046 (6)*
C12	0.15937 (12)	1.17870 (18)	0.59506 (11)	0.0223 (3)
H12	0.1724 (14)	1.233 (2)	0.6551 (14)	0.029 (5)*
O1	0.32101 (10)	0.49247 (14)	0.59478 (9)	0.0319 (3)
H1A	0.267 (2)	0.425 (3)	0.5696 (19)	0.063 (8)*
H1B	0.338 (2)	0.489 (3)	0.657 (2)	0.062 (8)*
O2	0.18478 (11)	0.50803 (14)	0.29669 (9)	0.0338 (3)
H2A	0.1662 (19)	0.516 (3)	0.228 (2)	0.059 (7)*
H2B	0.236 (2)	0.574 (3)	0.3215 (18)	0.057 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0310 (7)	0.0254 (7)	0.0194 (7)	0.0000 (5)	0.0098 (6)	−0.0008 (5)
N2	0.0284 (7)	0.0194 (6)	0.0187 (7)	−0.0009 (5)	0.0088 (6)	0.0015 (5)
N3	0.0334 (7)	0.0168 (6)	0.0204 (7)	−0.0023 (5)	0.0093 (6)	−0.0006 (5)
N4	0.0296 (7)	0.0188 (6)	0.0186 (6)	−0.0012 (5)	0.0097 (6)	−0.0003 (5)
N5	0.0310 (7)	0.0161 (6)	0.0233 (7)	−0.0029 (5)	0.0108 (6)	0.0002 (5)
C1	0.0207 (7)	0.0168 (7)	0.0195 (7)	−0.0003 (5)	0.0067 (6)	0.0003 (5)
C2	0.0208 (7)	0.0173 (7)	0.0184 (7)	0.0007 (5)	0.0062 (6)	0.0004 (5)
C3	0.0273 (8)	0.0213 (7)	0.0194 (8)	−0.0005 (6)	0.0095 (7)	−0.0018 (6)
C4	0.0219 (7)	0.0181 (7)	0.0175 (7)	0.0010 (5)	0.0062 (6)	0.0010 (5)
C5	0.0309 (8)	0.0175 (7)	0.0205 (8)	0.0000 (6)	0.0087 (7)	−0.0015 (6)
N6	0.0455 (9)	0.0294 (7)	0.0202 (7)	−0.0070 (6)	0.0122 (7)	−0.0020 (6)
C6	0.0364 (9)	0.0154 (7)	0.0269 (9)	−0.0009 (6)	0.0083 (8)	−0.0027 (6)
C7	0.0436 (10)	0.0242 (8)	0.0286 (9)	−0.0067 (7)	0.0159 (8)	0.0041 (7)
N7	0.0354 (8)	0.0226 (7)	0.0191 (7)	−0.0040 (5)	0.0095 (6)	0.0016 (5)
N8	0.0300 (7)	0.0181 (6)	0.0229 (7)	−0.0015 (5)	0.0094 (6)	−0.0006 (5)
N9	0.0249 (7)	0.0196 (6)	0.0202 (7)	0.0000 (5)	0.0087 (5)	0.0004 (5)
N10	0.0318 (7)	0.0168 (6)	0.0225 (7)	−0.0037 (5)	0.0090 (6)	0.0000 (5)
C8	0.0187 (7)	0.0172 (7)	0.0223 (8)	0.0004 (5)	0.0068 (6)	0.0011 (6)
C9	0.0250 (8)	0.0195 (7)	0.0199 (8)	−0.0016 (6)	0.0088 (6)	0.0006 (6)
C10	0.0390 (9)	0.0266 (8)	0.0205 (8)	−0.0062 (7)	0.0114 (7)	−0.0033 (6)
C11	0.0230 (8)	0.0201 (7)	0.0194 (8)	−0.0003 (6)	0.0075 (6)	0.0014 (6)
C13	0.0404 (10)	0.0238 (8)	0.0270 (9)	−0.0053 (7)	0.0114 (8)	0.0058 (6)
C14	0.0386 (10)	0.0184 (8)	0.0290 (9)	−0.0030 (6)	0.0114 (8)	−0.0042 (6)
C12	0.0271 (8)	0.0198 (7)	0.0203 (8)	0.0001 (6)	0.0085 (7)	−0.0024 (6)
O1	0.0510 (8)	0.0243 (6)	0.0212 (6)	−0.0113 (5)	0.0138 (6)	−0.0012 (5)
O2	0.0526 (8)	0.0265 (6)	0.0217 (6)	−0.0145 (5)	0.0124 (6)	−0.0012 (5)

Geometric parameters (Å, º) top

N1—C3	1.320 (2)	N7—C11	1.3456 (19)
N1—N2	1.3699 (18)	N7—H7	0.98 (2)
N2—C4	1.3456 (19)	N8—C12	1.320 (2)
N2—H2	0.94 (2)	N8—C11	1.3561 (19)
N3—C5	1.325 (2)	N9—C12	1.3460 (19)
N3—C4	1.3572 (19)	N9—C8	1.3534 (19)
N4—C5	1.3439 (19)	N10—C8	1.3408 (19)
N4—C1	1.3567 (19)	N10—C14	1.458 (2)
N5—C1	1.3404 (19)	N10—C13	1.459 (2)
N5—C6	1.454 (2)	C8—C9	1.424 (2)
N5—C7	1.459 (2)	C9—C11	1.403 (2)
C1—C2	1.427 (2)	C9—C10	1.422 (2)
C2—C4	1.402 (2)	C10—H10	1.01 (2)
C2—C3	1.425 (2)	C13—H13A	0.9800
C3—H3	0.98 (2)	C13—H13B	0.9800
C5—H5	0.99 (2)	C13—H13C	0.9800
N6—C10	1.321 (2)	C14—H14A	1.03 (2)
N6—N7	1.3687 (19)	C14—H14B	0.99 (3)
C6—H6A	0.97 (2)	C14—H14C	0.99 (2)
C6—H6B	1.00 (2)	C12—H12	0.97 (2)
C6—H6C	0.98 (2)	O1—H1A	0.93 (3)
C7—H7A	0.99 (3)	O1—H1B	0.88 (3)
C7—H7B	1.00 (2)	O2—H2A	0.97 (3)
C7—H7C	0.96 (3)	O2—H2B	0.89 (3)

C3—N1—N2	105.79 (13)	C11—N7—N6	111.25 (13)
C4—N2—N1	111.41 (12)	C11—N7—H7	131.4 (12)
C4—N2—H2	130.3 (14)	N6—N7—H7	117.4 (12)
N1—N2—H2	118.2 (14)	C12—N8—C11	111.35 (13)
C5—N3—C4	111.41 (12)	C12—N9—C8	118.61 (13)
C5—N4—C1	118.72 (13)	C8—N10—C14	120.94 (14)
C1—N5—C6	120.85 (13)	C8—N10—C13	121.10 (13)
C1—N5—C7	121.62 (13)	C14—N10—C13	117.72 (13)
C6—N5—C7	117.52 (13)	N10—C8—N9	117.78 (14)
N5—C1—N4	118.07 (13)	N10—C8—C9	123.85 (14)
N5—C1—C2	123.52 (14)	N9—C8—C9	118.37 (13)
N4—C1—C2	118.40 (13)	C11—C9—C10	103.55 (13)
C4—C2—C3	103.54 (13)	C11—C9—C8	115.65 (13)
C4—C2—C1	115.54 (13)	C10—C9—C8	140.79 (14)
C3—C2—C1	140.89 (14)	N6—C10—C9	111.55 (14)
N1—C3—C2	111.62 (13)	N6—C10—H10	120.8 (13)
N1—C3—H3	119.6 (11)	C9—C10—H10	127.7 (13)
C2—C3—H3	128.8 (11)	N7—C11—N8	125.67 (14)
N2—C4—N3	125.56 (13)	N7—C11—C9	107.70 (13)
N2—C4—C2	107.64 (13)	N8—C11—C9	126.62 (14)
N3—C4—C2	126.78 (14)	N10—C13—H13A	109.5
N3—C5—N4	129.15 (14)	N10—C13—H13B	109.5
N3—C5—H5	113.6 (11)	H13A—C13—H13B	109.5
N4—C5—H5	117.3 (11)	N10—C13—H13C	109.5
C10—N6—N7	105.95 (13)	H13A—C13—H13C	109.5
N5—C6—H6A	112.0 (13)	H13B—C13—H13C	109.5
N5—C6—H6B	110.4 (12)	N10—C14—H14A	111.6 (13)
H6A—C6—H6B	109.4 (17)	N10—C14—H14B	105.2 (14)
N5—C6—H6C	106.6 (13)	H14A—C14—H14B	114.7 (19)
H6A—C6—H6C	111.5 (18)	N10—C14—H14C	110.0 (13)
H6B—C6—H6C	106.9 (17)	H14A—C14—H14C	107.8 (18)
N5—C7—H7A	111.4 (16)	H14B—C14—H14C	107.3 (19)
N5—C7—H7B	110.2 (13)	N8—C12—N9	129.32 (14)
H7A—C7—H7B	109 (2)	N8—C12—H12	118.4 (11)
N5—C7—H7C	108.1 (16)	N9—C12—H12	112.3 (11)
H7A—C7—H7C	108 (2)	H1A—O1—H1B	107 (2)
H7B—C7—H7C	110 (2)	H2A—O2—H2B	106 (2)

C3—N1—N2—C4	0.35 (17)	C10—N6—N7—C11	−0.31 (19)
C6—N5—C1—N4	174.64 (14)	C14—N10—C8—N9	−174.25 (14)
C7—N5—C1—N4	−4.1 (2)	C13—N10—C8—N9	0.0 (2)
C6—N5—C1—C2	−6.3 (2)	C14—N10—C8—C9	5.4 (2)
C7—N5—C1—C2	174.90 (15)	C13—N10—C8—C9	179.64 (15)
C5—N4—C1—N5	179.26 (14)	C12—N9—C8—N10	177.22 (14)
C5—N4—C1—C2	0.2 (2)	C12—N9—C8—C9	−2.5 (2)
N5—C1—C2—C4	−179.67 (14)	N10—C8—C9—C11	−176.56 (14)
N4—C1—C2—C4	−0.6 (2)	N9—C8—C9—C11	3.1 (2)
N5—C1—C2—C3	−2.2 (3)	N10—C8—C9—C10	3.1 (3)
N4—C1—C2—C3	176.83 (18)	N9—C8—C9—C10	−177.20 (19)
N2—N1—C3—C2	−0.11 (18)	N7—N6—C10—C9	0.1 (2)
C4—C2—C3—N1	−0.15 (17)	C11—C9—C10—N6	0.2 (2)
C1—C2—C3—N1	−177.81 (18)	C8—C9—C10—N6	−179.54 (19)
N1—N2—C4—N3	177.86 (14)	N6—N7—C11—N8	−178.51 (15)
N1—N2—C4—C2	−0.45 (17)	N6—N7—C11—C9	0.43 (18)
C5—N3—C4—N2	−177.72 (15)	C12—N8—C11—N7	178.17 (15)
C5—N3—C4—C2	0.3 (2)	C12—N8—C11—C9	−0.6 (2)
C3—C2—C4—N2	0.35 (16)	C10—C9—C11—N7	−0.35 (17)
C1—C2—C4—N2	178.72 (13)	C8—C9—C11—N7	179.44 (13)
C3—C2—C4—N3	−177.93 (15)	C10—C9—C11—N8	178.57 (15)
C1—C2—C4—N3	0.4 (2)	C8—C9—C11—N8	−1.6 (2)
C4—N3—C5—N4	−0.9 (2)	C11—N8—C12—N9	1.5 (2)
C1—N4—C5—N3	0.7 (3)	C8—N9—C12—N8	0.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.94 (2)	1.82 (2)	2.7546 (18)	173 (2)
N7—H7···O2ⁱⁱ	0.99 (2)	1.74 (2)	2.7256 (19)	179 (3)
O1—H1A···N8ⁱ	0.93 (3)	1.94 (3)	2.8607 (19)	172 (2)
O1—H1B···N4ⁱⁱⁱ	0.88 (3)	1.95 (3)	2.8158 (18)	170 (2)
O2—H2A···N9^iv	0.97 (3)	1.86 (3)	2.8042 (18)	166 (2)
O2—H2B···N3ⁱⁱ	0.89 (3)	1.98 (3)	2.865 (2)	173 (2)

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

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.

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