2-Methyl-3-(3-methyl­isoxazol-5-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-1-ium chloride

Lahmidi, S.; El Ouasif, L.; Jilalat, A.E.; Al-Garadi, W.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314616019787

organic compounds

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ISSN: 2414-3146

Volume 1| Part 12| December 2016| x161978

https://doi.org/10.1107/S2414314616019787

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2-Methyl-3-(3-methylisoxazol-5-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-1-ium chloride

Sanae Lahmidi,^a ^* Latifa El Ouasif,^a Alae Eddine Jilalat,^a Wedad Al-Garadi,^a El Mokhtar Essassi ^a and Joel T. Mague ^b

^aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: lahmidi_sanae@yahoo.fr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 10 December 2016; accepted 11 December 2016; online 20 December 2016)

In the title molecular salt, C₁₃H₁₂N₃O₂⁺·Cl⁻, the oxazolyl ring is disordered over two orientations in a 0.536 (15):0.464 (15) ratio, both of which approximate to envelopes with the N atom as the flap in each case. The cation and anion are linked by a charge-assisted N—H⋯Cl hydrogen bond. In the extended structure, C—H⋯N, C—H⋯O and C—H⋯Cl interactions link the components into a three-dimensional network.

Keywords: crystal structure; hydrogen bond; pyridopyrimidinium chloride.

CCDC reference: 1521971

Structure description

Pyridopyrimidine compounds have found use as antimalarial agents (Mane et al., 2014 ), anti-allergic agents (Awouters et al., 1986 ) and urease inhibitors (Rauf et al., 2012 ). The isoxazole nucleus is known to exhibit anticancer (Han et al., 2002 ), anti-HIV (Deng et al., 2006 ) and fungicide (Raffa et al., 1999 ) activities. The present work reporting the synthesis and structure of the title molecular salt (Fig. 1) is a continuation of our work on pyridopyrimidine derivatives (Djerrari et al., 2002 ).

Figure 1
The title molecule with the atom-labelling scheme and 25% probability ellipsoids. The N—H⋯Cl hydrogen bond is shown as a dotted line. Only the major component of the disorder in the oxazolyl substituent is shown.

The bicyclic core of the cation is slightly folded along the C5—N1 axis by 1.07 (14)°. In the oxazolyl substituent, the oxygen and nitrogen atoms and the C—CH₃ grouping are disordered over two sets of sites, which represent the two possible envelope conformations of the five-membered ring (flap atom = N). The cation and anion are strongly associated through the N2—H2A⋯Cl1 hydrogen bond (Table 1 and Fig. 1). In the extended structure, the ion pairs are arranged in rows running along the a-axis direction with weak, bifurcated C13A—H13A⋯O2Aⁱ and C13A—H13A⋯N3Aⁱ [symmetry code: (i) $[{1\over 2}]$ − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z] hydrogen bonds (Table 1 and Fig. 2) as well as weak C—H⋯Cl interactions.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1A⋯Cl1	0.88 (4)	2.15 (4)	3.024 (3)	177 (3)
C2—H2⋯Cl1ⁱ	0.98 (4)	2.78 (4)	3.745 (4)	173 (2)
C3—H3⋯Cl1ⁱⁱ	0.98 (4)	2.71 (4)	3.445 (3)	132 (3)
C11—H11⋯N3Aⁱⁱⁱ	0.90 (4)	2.67 (4)	3.390 (16)	138 (3)
C13A—H13A⋯O2Aⁱⁱⁱ	0.96	2.34	3.21 (4)	151
C13A—H13A⋯N3Aⁱⁱⁱ	0.96	2.50	3.37 (4)	150
Symmetry codes: (i) x, y+1, z; (ii) -x+3, -y+1, -z+1; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
Packing viewed along the a axis. N—H⋯Cl and C–H⋯O hydrogen bonds are shown, respectively, as blue and black dotted lines.

Synthesis and crystallization

A mixture of 1-(2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)butane-1,3-dione (0.7 g, 2.86 mmol) and of hydroxylamine hydrochloride (0.4 g, 5.75 mmol) in methanol (30 ml) was heated at reflux for 4 h. The completion of the reaction was confirmed by TLC. The solid obtained upon cooling the mixture was recrystallized from ethanol solution to afford orange blocks (yield: 76%. m.p.: 465–467 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. In the pendant oxazolyl substituent, all atoms except C10 and C11 are disordered over two sets of sites in a 0.536 (15):0.464 (15) ratio. The two components of the disorder were refined with restraints that their geometries be comparable.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₃O₂⁺·Cl⁻
M_r	277.70
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.2796 (12), 9.6912 (18), 21.152 (4)
β (°)	95.294 (3)
V (Å³)	1281.8 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.30
Crystal size (mm)	0.32 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (TWINABS; Sheldrick, 2009 )
T_min, T_max	0.75, 0.94
No. of measured, independent and observed [I > 2σ(I)] reflections	28190, 6596, 4582
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.678

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.192, 1.04
No. of reflections	6596
No. of parameters	222
No. of restraints	53
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.33
Computer programs: APEX3 and SAINT (Bruker, 2016 ), CELL_NOW (Sheldrick, 2008a ) and SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008b ).

Structural data

CCDC reference: 1521971

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616019787/hb4105sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616019787/hb4105Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616019787/hb4105Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314616019787/hb4105Isup4.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: CELL_NOW (Sheldrick, 2008a) and 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, 2008b).

2-Methyl-3-(3-methylisoxazol-5-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-1-ium chloride top

Crystal data top

C₁₃H₁₂N₃O₂⁺·Cl⁻	F(000) = 576
M_r = 277.70	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.2796 (12) Å	Cell parameters from 5128 reflections
b = 9.6912 (18) Å	θ = 2.3–25.9°
c = 21.152 (4) Å	µ = 0.30 mm⁻¹
β = 95.294 (3)°	T = 298 K
V = 1281.8 (4) Å³	Block, orange
Z = 4	0.32 × 0.20 × 0.19 mm

Data collection top

Bruker SMART APEX CCD diffractometer	6596 independent reflections
Radiation source: fine-focus sealed tube	4582 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.8°, θ_min = 1.9°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −13→13
T_min = 0.75, T_max = 0.94	l = −28→28
28190 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)] = 0.064	Hydrogen site location: mixed
wR(F²) = 0.192	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0802P)² + 0.5444P] where P = (F_o² + 2F_c²)/3
6596 reflections	(Δ/σ)_max = 0.001
222 parameters	Δρ_max = 0.36 e Å⁻³
53 restraints	Δρ_min = −0.33 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 20 sec/frame. Analysis of 1600 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008a) showed the crystal to belong to the monoclinic system and to be twinned by a 180° rotation about the c* axis. The raw data were processed using the multi- component version of SAINT under control of the two-component orientation file generated by CELL_NOW.

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. The methyl oxazole moiety is disordered over two partially resolved sites with the disorder mainly involving alternate conformations of the heteroatom prtion of the ring.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.6819 (4)	0.8510 (2)	0.65445 (14)	0.0747 (8)
N1	0.9648 (4)	0.7726 (2)	0.60427 (12)	0.0472 (6)
H1A	1.092 (5)	0.470 (4)	0.5794 (15)	0.048 (8)*
N2	1.0175 (4)	0.5368 (3)	0.59451 (11)	0.0460 (6)
O2A	0.497 (2)	0.4524 (5)	0.7017 (5)	0.067 (2)	0.536 (15)
N3A	0.374 (2)	0.4582 (16)	0.7600 (5)	0.068 (3)	0.536 (15)
O2B	0.549 (2)	0.4604 (7)	0.7216 (6)	0.067 (2)	0.464 (15)
N3B	0.320 (2)	0.4573 (19)	0.7389 (7)	0.068 (3)	0.464 (15)
C1	1.0220 (6)	0.9076 (3)	0.59290 (16)	0.0571 (8)
H1	0.933 (6)	0.971 (4)	0.6091 (17)	0.063 (10)*
C2	1.1882 (6)	0.9357 (4)	0.55943 (17)	0.0614 (8)
H2	1.227 (5)	1.032 (4)	0.5534 (15)	0.058 (9)*
C3	1.3048 (5)	0.8268 (4)	0.53573 (16)	0.0578 (8)
H3	1.424 (6)	0.848 (4)	0.5106 (16)	0.060 (9)*
C4	1.2516 (5)	0.6939 (3)	0.54654 (14)	0.0505 (7)
H4	1.327 (5)	0.616 (3)	0.5311 (14)	0.046 (8)*
C5	1.0770 (5)	0.6671 (3)	0.58186 (13)	0.0448 (6)
C7	0.7321 (5)	0.6085 (3)	0.65240 (13)	0.0450 (6)
C6	0.8520 (5)	0.5045 (3)	0.62902 (13)	0.0445 (6)
C9	0.8178 (6)	0.3526 (3)	0.6367 (2)	0.0566 (8)
H9A	0.841 (7)	0.328 (4)	0.678 (2)	0.090 (14)*
H9B	0.685 (7)	0.327 (4)	0.6228 (19)	0.075 (12)*
H9C	0.921 (7)	0.298 (5)	0.614 (2)	0.089 (13)*
C8	0.7780 (5)	0.7504 (3)	0.63969 (15)	0.0510 (7)
C10	0.5567 (5)	0.5859 (3)	0.69230 (13)	0.0476 (7)
C11	0.4164 (5)	0.6703 (3)	0.71767 (15)	0.0510 (7)
H11	0.400 (6)	0.762 (4)	0.7120 (16)	0.065 (11)*
C12A	0.279 (3)	0.5827 (14)	0.7485 (9)	0.046 (3)	0.536 (15)
C13A	0.117 (4)	0.630 (4)	0.7921 (13)	0.059 (2)	0.536 (15)
H13A	0.0628	0.7190	0.7787	0.089*	0.536 (15)
H13B	0.0014	0.5650	0.7908	0.089*	0.536 (15)
H13C	0.1839	0.6364	0.8347	0.089*	0.536 (15)
C12B	0.306 (4)	0.5894 (16)	0.7596 (11)	0.046 (3)	0.464 (15)
C13B	0.110 (5)	0.617 (5)	0.7933 (15)	0.059 (2)	0.464 (15)
H13D	0.1091	0.7114	0.8067	0.089*	0.464 (15)
H13E	−0.0157	0.5989	0.7649	0.089*	0.464 (15)
H13F	0.1097	0.5576	0.8297	0.089*	0.464 (15)
Cl1	1.28278 (13)	0.31411 (8)	0.53955 (4)	0.0574 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0733 (16)	0.0429 (12)	0.115 (2)	0.0045 (11)	0.0483 (15)	−0.0048 (13)
N1	0.0485 (13)	0.0420 (12)	0.0527 (13)	−0.0001 (10)	0.0139 (11)	−0.0023 (10)
N2	0.0463 (13)	0.0418 (12)	0.0514 (13)	0.0045 (10)	0.0130 (11)	−0.0006 (10)
O2A	0.088 (5)	0.0476 (14)	0.073 (5)	−0.0073 (16)	0.045 (4)	−0.008 (2)
N3A	0.090 (6)	0.0550 (18)	0.065 (6)	−0.004 (4)	0.042 (5)	−0.002 (5)
O2B	0.088 (5)	0.0476 (14)	0.073 (5)	−0.0073 (16)	0.045 (4)	−0.008 (2)
N3B	0.090 (6)	0.0550 (18)	0.065 (6)	−0.004 (4)	0.042 (5)	−0.002 (5)
C1	0.063 (2)	0.0418 (16)	0.069 (2)	−0.0008 (14)	0.0182 (16)	−0.0025 (14)
C2	0.067 (2)	0.0487 (18)	0.071 (2)	−0.0085 (15)	0.0187 (17)	0.0023 (15)
C3	0.0541 (18)	0.0594 (19)	0.0626 (19)	−0.0049 (15)	0.0190 (15)	0.0000 (15)
C4	0.0468 (16)	0.0529 (17)	0.0538 (16)	0.0014 (13)	0.0149 (13)	−0.0018 (13)
C5	0.0451 (14)	0.0425 (14)	0.0475 (15)	0.0017 (11)	0.0076 (12)	−0.0004 (11)
C7	0.0470 (15)	0.0427 (14)	0.0465 (14)	0.0010 (12)	0.0111 (12)	−0.0025 (11)
C6	0.0449 (14)	0.0424 (14)	0.0466 (14)	0.0020 (11)	0.0065 (12)	0.0016 (11)
C9	0.058 (2)	0.0432 (16)	0.071 (2)	0.0025 (15)	0.0213 (18)	0.0033 (15)
C8	0.0477 (16)	0.0471 (16)	0.0603 (17)	0.0009 (13)	0.0168 (14)	−0.0031 (13)
C10	0.0522 (16)	0.0436 (15)	0.0480 (15)	−0.0021 (12)	0.0106 (12)	−0.0031 (12)
C11	0.0510 (17)	0.0476 (17)	0.0565 (17)	0.0006 (13)	0.0172 (13)	−0.0001 (13)
C12A	0.049 (4)	0.0526 (19)	0.037 (6)	−0.008 (2)	0.006 (5)	−0.010 (3)
C13A	0.064 (2)	0.055 (6)	0.063 (2)	−0.007 (3)	0.0261 (17)	−0.004 (2)
C12B	0.049 (4)	0.0526 (19)	0.037 (6)	−0.008 (2)	0.006 (5)	−0.010 (3)
C13B	0.064 (2)	0.055 (6)	0.063 (2)	−0.007 (3)	0.0261 (17)	−0.004 (2)
Cl1	0.0549 (4)	0.0508 (4)	0.0684 (5)	0.0076 (3)	0.0152 (4)	−0.0032 (3)

Geometric parameters (Å, º) top

O1—C8	1.203 (4)	C4—H4	0.96 (3)
N1—C5	1.352 (4)	C7—C6	1.377 (4)
N1—C1	1.383 (4)	C7—C8	1.436 (4)
N1—C8	1.465 (4)	C7—C10	1.465 (4)
N2—C5	1.351 (4)	C6—C9	1.498 (4)
N2—C6	1.360 (4)	C9—H9C	0.99 (4)
N2—H1A	0.88 (4)	C9—H9B	0.89 (4)
O2A—C10	1.368 (5)	C9—H9A	0.90 (5)
O2A—N3A	1.513 (6)	C10—C11	1.349 (4)
N3A—C12A	1.359 (10)	C11—C12B	1.412 (5)
O2B—C10	1.368 (5)	C11—C12A	1.412 (5)
O2B—N3B	1.515 (7)	C11—H11	0.90 (4)
N3B—C12B	1.358 (10)	C12A—C13A	1.506 (7)
C1—C2	1.342 (5)	C13A—H13A	0.9600
C1—H1	0.92 (4)	C13A—H13B	0.9600
C2—C3	1.403 (5)	C13A—H13C	0.9600
C2—H2	0.97 (4)	C12B—C13B	1.506 (7)
C3—C4	1.355 (5)	C13B—H13D	0.9600
C3—H3	0.98 (4)	C13B—H13E	0.9600
C4—C5	1.407 (4)	C13B—H13F	0.9600

C5—N1—C1	120.1 (3)	C6—C9—H9A	112 (3)
C5—N1—C8	122.4 (2)	H9C—C9—H9A	105 (4)
C1—N1—C8	117.5 (2)	H9B—C9—H9A	109 (3)
C5—N2—C6	124.1 (3)	O1—C8—C7	127.9 (3)
C5—N2—H1A	117 (2)	O1—C8—N1	117.3 (3)
C6—N2—H1A	119 (2)	C7—C8—N1	114.9 (2)
C10—O2A—N3A	104.6 (9)	C11—C10—O2A	108.5 (6)
C12A—N3A—O2A	97.7 (12)	C11—C10—O2B	107.8 (6)
C10—O2B—N3B	101.7 (10)	C11—C10—C7	133.8 (3)
C12B—N3B—O2B	98.5 (15)	O2A—C10—C7	117.2 (5)
C2—C1—N1	120.8 (3)	O2B—C10—C7	117.1 (6)
C2—C1—H1	126 (2)	C10—C11—C12B	106.8 (9)
N1—C1—H1	113 (2)	C10—C11—C12A	105.6 (7)
C1—C2—C3	119.5 (3)	C10—C11—H11	128 (2)
C1—C2—H2	119 (2)	C12B—C11—H11	125 (2)
C3—C2—H2	122 (2)	C12A—C11—H11	126 (2)
C4—C3—C2	120.7 (3)	N3A—C12A—C11	109.9 (13)
C4—C3—H3	120 (2)	N3A—C12A—C13A	118.1 (16)
C2—C3—H3	119 (2)	C11—C12A—C13A	125.1 (19)
C3—C4—C5	118.8 (3)	C12A—C13A—H13A	109.5
C3—C4—H4	123.6 (19)	C12A—C13A—H13B	109.5
C5—C4—H4	117.6 (19)	H13A—C13A—H13B	109.5
N2—C5—N1	118.3 (3)	C12A—C13A—H13C	109.5
N2—C5—C4	121.4 (3)	H13A—C13A—H13C	109.5
N1—C5—C4	120.2 (3)	H13B—C13A—H13C	109.5
C6—C7—C8	120.5 (3)	N3B—C12B—C11	105.8 (13)
C6—C7—C10	124.3 (3)	N3B—C12B—C13B	113 (2)
C8—C7—C10	115.2 (2)	C11—C12B—C13B	132 (2)
N2—C6—C7	119.6 (3)	C12B—C13B—H13D	109.5
N2—C6—C9	114.1 (3)	C12B—C13B—H13E	109.5
C7—C6—C9	126.3 (3)	H13D—C13B—H13E	109.5
C6—C9—H9C	111 (3)	C12B—C13B—H13F	109.5
C6—C9—H9B	112 (3)	H13D—C13B—H13F	109.5
H9C—C9—H9B	108 (4)	H13E—C13B—H13F	109.5

C10—O2A—N3A—C12A	35.8 (19)	C1—N1—C8—O1	2.8 (5)
C10—O2B—N3B—C12B	−42.4 (18)	C5—N1—C8—C7	4.0 (4)
C5—N1—C1—C2	0.3 (5)	C1—N1—C8—C7	−177.4 (3)
C8—N1—C1—C2	−178.4 (3)	N3A—O2A—C10—C11	−25.9 (13)
N1—C1—C2—C3	0.0 (6)	N3A—O2A—C10—C7	161.2 (9)
C1—C2—C3—C4	−0.2 (6)	N3B—O2B—C10—C11	29.1 (12)
C2—C3—C4—C5	0.1 (5)	N3B—O2B—C10—C7	−162.2 (8)
C6—N2—C5—N1	−0.6 (4)	C6—C7—C10—C11	−177.0 (3)
C6—N2—C5—C4	179.2 (3)	C8—C7—C10—C11	4.6 (5)
C1—N1—C5—N2	179.3 (3)	C6—C7—C10—O2A	−6.3 (8)
C8—N1—C5—N2	−2.1 (4)	C8—C7—C10—O2A	175.2 (7)
C1—N1—C5—C4	−0.4 (4)	C6—C7—C10—O2B	18.1 (8)
C8—N1—C5—C4	178.2 (3)	C8—C7—C10—O2B	−160.4 (7)
C3—C4—C5—N2	−179.5 (3)	O2B—C10—C11—C12B	−5.3 (14)
C3—C4—C5—N1	0.2 (5)	C7—C10—C11—C12B	−171.3 (13)
C5—N2—C6—C7	1.1 (4)	O2A—C10—C11—C12A	5.4 (12)
C5—N2—C6—C9	−179.8 (3)	C7—C10—C11—C12A	176.6 (11)
C8—C7—C6—N2	1.1 (4)	O2A—N3A—C12A—C11	−33 (2)
C10—C7—C6—N2	−177.3 (3)	O2A—N3A—C12A—C13A	174 (2)
C8—C7—C6—C9	−177.9 (3)	C10—C11—C12A—N3A	20.2 (19)
C10—C7—C6—C9	3.8 (5)	C10—C11—C12A—C13A	170 (2)
C6—C7—C8—O1	176.4 (4)	O2B—N3B—C12B—C11	40 (2)
C10—C7—C8—O1	−5.1 (5)	O2B—N3B—C12B—C13B	−169 (2)
C6—C7—C8—N1	−3.4 (4)	C10—C11—C12B—N3B	−24 (2)
C10—C7—C8—N1	175.1 (3)	C10—C11—C12B—C13B	−168 (3)
C5—N1—C8—O1	−175.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1A···Cl1	0.88 (4)	2.15 (4)	3.024 (3)	177 (3)
C2—H2···Cl1ⁱ	0.98 (4)	2.78 (4)	3.745 (4)	173 (2)
C3—H3···Cl1ⁱⁱ	0.98 (4)	2.71 (4)	3.445 (3)	132 (3)
C11—H11···N3Aⁱⁱⁱ	0.90 (4)	2.67 (4)	3.390 (16)	138 (3)
C13A—H13A···O2Aⁱⁱⁱ	0.96	2.34	3.21 (4)	151
C13A—H13A···N3Aⁱⁱⁱ	0.96	2.50	3.37 (4)	150

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