(−)-Sparteinium tetra­chlorido­zincate monohydrate

Bernès, S.; Gutiérrez, R.; Hernández-Téllez, G.; Moreno, G.E.

doi:10.1107/S2414314616012372

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 8| August 2016| x161237

doi:10.1107/S2414314616012372

Open

access

(−)-Sparteinium tetrachloridozincate monohydrate

Sylvain Bernès,^a ^* René Gutiérrez,^b Guadalupe Hernández-Téllez ^b and Gloria E. Moreno ^b

^aInstituto de Física, Universidad Autónoma de Puebla, Av. San Claudio y 18 Sur, 72570 Puebla, Pue., Mexico, and ^bLaboratorio de Síntesis de Complejos, Facultad de Ciencias Químicas, Universidad Autónoma de Puebla, A.P. 1067, 72001 Puebla, Pue., Mexico
^*Correspondence e-mail: sylvain_bernes@hotmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 14 July 2016; accepted 31 July 2016; online 9 August 2016)

The title ionic compound, (C₁₅H₂₈N₂)[ZnCl₄]·H₂O, is isostructural with the Cu^II analogue published previously [Lee et al. (2004 ). Bull. Korean Chem. Soc. 25, 823–828; Jasiewicz et al. (2006 ). J. Mol. Struct. 794, 311–319]. The [ZnCl₄]²⁻ anion is, however, much more close to the tetrahedral conformation than the [CuCl₄]²⁻ ion. In the tetrachloridozincate anion, the Cl—Zn—Cl angles are in the range 103.57 (3)–116.81 (3)°.

Keywords: crystal structure; sparteine; zinc; hydrate.

CCDC reference: 1497008

Structure description

The orthorhombic unit cell for the title compound (esp)²⁺(ZnCl₄)²⁻·H₂O (Fig. 1) has parameters close to those reported for the copper analogue, (esp)²⁺(CuCl₄)²⁻·H₂O, and both complexes crystallize in the same chiral space group, P2₁2₁2₁ [Lee et al., 2004; Jasiewicz et al., 2006; CSD (Groom et al., 2016 ) refcodes CANVOD and CANVOD01, respectively]. The ligand esp is sparteine, also known as lupinidine, an alkaloid having four chiral centres and two protonable N sites. For the structure reported here, (–)-sparteine was used, which has the RSSS configuration (Hoppe & Hense, 1997 ). The same arrangement of ions and lattice water in the crystal is observed with Zn^II and Cu^II. However, the tetrachloridozincate ion is almost tetrahedral, while the Cu analogue, (CuCl₄)²⁻, with one electron less, is strongly distorted. For the structure reported here, the Cl—Zn—Cl angles are in the range 103.57 (3)–116.81 (3)°, while the Cl—Cu—Cl angles are in the range 97.9–135.3° (Lee et al., 2004) or 97.8–135.3° (Jasiewicz et al., 2006). This difference may be quantitatively estimated using the τ₄′ parameter defined for four-coordinate atoms (Okuniewski et al., 2015 ; extreme values for τ₄′ are 0 for a square planar and 1 for a tetrahedral conformation). In the title complex, τ₄′ = 0.92 for (ZnCl₄)²⁻, while in the case of CANVOD and CANVOD01, τ₄′ = 0.69 for (CuCl₄)²⁻.

Figure 1
The structures of the molecular entities of the title compound, with displacement ellipsoids for non-H atoms drawn at the 30% probability level. The choice for the asymmetric unit, as well as the labelling scheme (including H atoms), are the same as for CANVOD (Lee et al., 2004

With Cu^II, the isotypic complex was synthesized with (CuBr₄)²⁻ (Lee et al., 2004). The last (–)-sparteinium salt for which a crystal structure has been reported was also obtained as an hydrate, with a complex heteropolyoxidometalate anion (Streb et al., 2007 ). The dication of the α-isomer of sparteine has also been characterized, with (CuCl₄)²⁻ or (CuBr₄)²⁻, both crystallized as monohydrate species (Jasiewicz et al., 2006).

Regardless of the (MX₄)²⁻ dianion used with (esp)²⁺, the inclusion of a water molecule in the lattice seems to be a stabilizing factor for the compound. For the title compound, this molecule behaves as acceptor and donor for hydrogen bonding (Table 1, entries 2–5). The crystal cohesion is completed with an N—H⋯Cl contact linking cations and anions (Table 1, entry 1; Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1ⁱ	0.98	2.31	3.279 (2)	170
N2—H2⋯O1ⁱⁱ	0.98	1.83	2.798 (3)	168
O1—H30⋯Cl2ⁱ	0.85 (1)	2.71 (4)	3.355 (3)	133 (4)
O1—H30⋯Cl3ⁱ	0.85 (1)	2.76 (3)	3.473 (3)	143 (4)
O1—H29⋯Cl1ⁱⁱⁱ	0.86 (1)	2.42 (1)	3.257 (3)	167 (4)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Figure 2
Part of the crystal structure, showing hydrogen bonds (dashed lines) and omitting H atoms not involved in hydrogen bonding. Hydrogen bonds are labelled (1)–(5), which correspond to entries 1–5 in Table 1

Synthesis and crystallization

The compound was obtained as a low-yield by-product during the direct synthesis of the Zn^II coordination complex [Zn(esp)Cl(PhCOO)], for which the crystal structure has been reported (Alcántara-Flores et al., 2009 ). The synthesis of this complex was carried out using equimolar amounts of zinc powder and (–)-sparteine, an excess of benzoyl chloride, and DMSO. The mixture was stirred at 338 K for 8 h, cooled, and filtered. In this kind of reaction, the oxidative dissolution of zerovalent metals M⁰ in presence of an acyl halide has been shown to afford small quantities of (MX₄)²⁻, and water is provided by DMSO (Garnovskii et al., 1995 ).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The structure was refined starting from the atomic coordinates reported for CANVOD (Lee et al., 2004), after substituting the Cu site by a Zn site.

Table 2
Experimental details

Crystal data
Chemical formula	(C₁₅H₂₈N₂)[ZnCl₄]·H₂O
M_r	461.58
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	297
a, b, c (Å)	8.4549 (6), 14.7691 (10), 16.3607 (9)
V (Å³)	2043.0 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.73
Crystal size (mm)	0.5 × 0.5 × 0.5

Data collection
Diffractometer	Bruker P4
Absorption correction	ψ scan (XSCANS; Bruker, 1997 )
T_min, T_max	0.210, 0.277
No. of measured, independent and observed [I > 2σ(I)] reflections	4207, 3989, 3673
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.068, 1.05
No. of reflections	3989
No. of parameters	215
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.27
Absolute structure	Flack x determined using 593 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.004 (11)
Computer programs: XSCANS (Bruker, 1997), SHELXL2014 (Sheldrick, 2015 ), XP in SHELXTL (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1497008

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616012372/wm4021sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616012372/wm4021Isup2.hkl

checkCIF report

Computing details top

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS (Bruker, 1997); data reduction: XSCANS (Bruker, 1997); program(s) used to solve structure: coordinates taken from an isostructural compound; program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(-)-7,15-Diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadecane-7,15-diium tetrachloridozincate monohydrate top

Crystal data top

(C₁₅H₂₈N₂)[ZnCl₄]·H₂O	D_x = 1.501 Mg m⁻³
M_r = 461.58	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 65 reflections
a = 8.4549 (6) Å	θ = 4.6–14.0°
b = 14.7691 (10) Å	µ = 1.73 mm⁻¹
c = 16.3607 (9) Å	T = 297 K
V = 2043.0 (2) Å³	Prism, pale_yellow
Z = 4	0.5 × 0.5 × 0.5 mm
F(000) = 960

Data collection top

Bruker P4 diffractometer	3673 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.017
Graphite monochromator	θ_max = 30.0°, θ_min = 1.9°
2θ/ω scans	h = −11→1
Absorption correction: ψ scan (XSCANS; Bruker, 1997)	k = −20→1
T_min = 0.210, T_max = 0.277	l = −1→23
4207 measured reflections	3 standard reflections every 97 reflections
3989 independent reflections	intensity decay: 1.5%

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.027	w = 1/[σ²(F_o²) + (0.0309P)² + 0.3509P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.068	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.26 e Å⁻³
3989 reflections	Δρ_min = −0.27 e Å⁻³
215 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0095 (6)
0 constraints	Absolute structure: Flack x determined using 593 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: isomorphous structure methods	Absolute structure parameter: −0.004 (11)
Secondary atom site location: difference Fourier map

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

	x	y	z	U_iso*/U_eq
Zn1	0.47336 (4)	0.00375 (2)	0.13525 (2)	0.03925 (8)
Cl1	0.43251 (8)	−0.14733 (4)	0.17192 (4)	0.04092 (14)
Cl2	0.60888 (9)	0.06123 (4)	0.24235 (4)	0.04872 (16)
Cl3	0.23318 (10)	0.07286 (6)	0.13219 (6)	0.0611 (2)
Cl4	0.59037 (10)	0.01131 (6)	0.01301 (4)	0.0581 (2)
N1	0.7771 (3)	0.39420 (14)	0.16364 (12)	0.0352 (4)
H1	0.7235	0.3756	0.2140	0.042*
N2	1.0034 (3)	0.25994 (14)	0.31415 (12)	0.0378 (4)
H2	1.1143	0.2420	0.3078	0.045*
C1	0.6597 (4)	0.44897 (19)	0.11347 (17)	0.0485 (7)
H3	0.6328	0.5041	0.1426	0.058*
H4	0.7076	0.4658	0.0618	0.058*
C2	0.5127 (4)	0.3951 (3)	0.0979 (2)	0.0611 (8)
H5	0.4415	0.4299	0.0636	0.073*
H6	0.4595	0.3832	0.1493	0.073*
C3	0.5513 (5)	0.3052 (2)	0.05581 (19)	0.0605 (9)
H7	0.4561	0.2689	0.0519	0.073*
H8	0.5890	0.3169	0.0008	0.073*
C4	0.6767 (4)	0.25307 (19)	0.10303 (17)	0.0514 (7)
H9	0.6331	0.2341	0.1551	0.062*
H10	0.7050	0.1991	0.0726	0.062*
C5	0.8241 (4)	0.30901 (16)	0.11801 (14)	0.0388 (5)
H11	0.8644	0.3278	0.0645	0.047*
C6	0.9576 (4)	0.25900 (17)	0.16147 (15)	0.0403 (5)
H12	0.9900	0.2087	0.1262	0.048*
C7	1.0478 (3)	0.39856 (18)	0.22780 (15)	0.0418 (5)
H13	1.1381	0.4392	0.2355	0.050*
C8	0.9460 (4)	0.2225 (2)	0.39410 (16)	0.0497 (7)
H14	0.9533	0.1570	0.3931	0.060*
H15	0.8358	0.2388	0.4018	0.060*
C9	1.0428 (5)	0.2589 (3)	0.46439 (18)	0.0661 (9)
H16	1.1502	0.2363	0.4602	0.079*
H17	0.9986	0.2373	0.5155	0.079*
C10	1.0455 (5)	0.3613 (3)	0.46488 (18)	0.0653 (9)
H18	1.1169	0.3824	0.5072	0.078*
H19	0.9405	0.3840	0.4773	0.078*
C11	1.0988 (4)	0.3981 (2)	0.38265 (17)	0.0531 (7)
H20	1.0929	0.4637	0.3834	0.064*
H21	1.2081	0.3812	0.3733	0.064*
C12	0.9973 (3)	0.36208 (16)	0.31331 (15)	0.0374 (5)
H22	0.8878	0.3807	0.3233	0.045*
C13	0.9161 (3)	0.45208 (16)	0.18746 (15)	0.0415 (6)
H23	0.8806	0.4989	0.2247	0.050*
H24	0.9575	0.4816	0.1390	0.050*
C14	0.9123 (3)	0.21852 (17)	0.24551 (15)	0.0411 (5)
H25	0.8002	0.2278	0.2549	0.049*
H26	0.9316	0.1538	0.2447	0.049*
C15	1.0995 (3)	0.3218 (2)	0.17079 (18)	0.0481 (6)
H27	1.1309	0.3458	0.1180	0.058*
H28	1.1885	0.2893	0.1941	0.058*
O1	0.6895 (3)	0.68939 (18)	0.1878 (2)	0.0692 (7)
H29	0.615 (4)	0.728 (3)	0.191 (3)	0.104*
H30	0.663 (6)	0.652 (2)	0.225 (2)	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.04187 (15)	0.03891 (14)	0.03698 (13)	0.00235 (14)	−0.00004 (12)	0.00472 (12)
Cl1	0.0427 (3)	0.0356 (2)	0.0444 (3)	0.0003 (2)	0.0092 (3)	0.0001 (2)
Cl2	0.0510 (4)	0.0450 (3)	0.0501 (3)	−0.0082 (3)	−0.0069 (3)	0.0003 (3)
Cl3	0.0533 (4)	0.0619 (4)	0.0682 (4)	0.0224 (4)	−0.0027 (4)	0.0087 (4)
Cl4	0.0641 (4)	0.0739 (5)	0.0364 (3)	0.0058 (4)	0.0041 (3)	0.0145 (3)
N1	0.0422 (10)	0.0339 (9)	0.0295 (8)	−0.0015 (9)	0.0028 (9)	−0.0006 (7)
N2	0.0337 (11)	0.0444 (10)	0.0353 (9)	−0.0008 (9)	0.0005 (9)	0.0061 (8)
C1	0.0596 (17)	0.0436 (13)	0.0423 (13)	0.0089 (14)	−0.0058 (13)	0.0032 (11)
C2	0.0538 (18)	0.077 (2)	0.0529 (16)	0.0031 (18)	−0.0186 (16)	0.0067 (15)
C3	0.072 (2)	0.0652 (18)	0.0442 (13)	−0.0149 (18)	−0.0240 (16)	0.0035 (13)
C4	0.070 (2)	0.0438 (13)	0.0408 (12)	−0.0132 (14)	−0.0098 (14)	−0.0037 (11)
C5	0.0534 (15)	0.0347 (11)	0.0284 (10)	−0.0007 (11)	0.0024 (10)	−0.0019 (8)
C6	0.0469 (14)	0.0394 (11)	0.0346 (10)	0.0054 (12)	0.0081 (11)	−0.0020 (9)
C7	0.0362 (12)	0.0465 (12)	0.0429 (12)	−0.0138 (11)	0.0015 (11)	0.0050 (10)
C8	0.0524 (17)	0.0590 (15)	0.0376 (11)	−0.0026 (15)	0.0018 (13)	0.0153 (11)
C9	0.070 (2)	0.087 (2)	0.0411 (14)	0.006 (2)	−0.0077 (16)	0.0119 (15)
C10	0.069 (2)	0.086 (2)	0.0410 (14)	−0.002 (2)	−0.0115 (16)	−0.0094 (14)
C11	0.0483 (16)	0.0615 (16)	0.0497 (15)	−0.0074 (15)	−0.0099 (13)	−0.0073 (13)
C12	0.0326 (12)	0.0416 (11)	0.0379 (11)	−0.0026 (10)	−0.0022 (10)	0.0013 (9)
C13	0.0505 (14)	0.0336 (10)	0.0405 (12)	−0.0108 (11)	0.0020 (12)	0.0034 (9)
C14	0.0476 (14)	0.0364 (11)	0.0392 (12)	−0.0018 (11)	−0.0011 (12)	0.0014 (9)
C15	0.0380 (13)	0.0614 (16)	0.0448 (13)	0.0011 (13)	0.0136 (12)	0.0105 (13)
O1	0.0514 (13)	0.0620 (14)	0.0942 (19)	−0.0091 (11)	0.0106 (15)	0.0043 (14)

Geometric parameters (Å, º) top

Zn1—Cl4	2.2341 (7)	C6—C14	1.547 (3)
Zn1—Cl2	2.2592 (7)	C6—H12	0.9800
Zn1—Cl3	2.2734 (8)	C7—C13	1.516 (4)
Zn1—Cl1	2.3362 (7)	C7—C15	1.532 (4)
N1—C13	1.505 (3)	C7—C12	1.559 (3)
N1—C5	1.516 (3)	C7—H13	0.9800
N1—C1	1.521 (3)	C8—C9	1.511 (5)
N1—H1	0.9800	C8—H14	0.9700
N2—C14	1.493 (3)	C8—H15	0.9700
N2—C8	1.501 (3)	C9—C10	1.513 (5)
N2—C12	1.509 (3)	C9—H16	0.9700
N2—H2	0.9800	C9—H17	0.9700
C1—C2	1.498 (5)	C10—C11	1.519 (4)
C1—H3	0.9700	C10—H18	0.9700
C1—H4	0.9700	C10—H19	0.9700
C2—C3	1.530 (5)	C11—C12	1.518 (4)
C2—H5	0.9700	C11—H20	0.9700
C2—H6	0.9700	C11—H21	0.9700
C3—C4	1.521 (5)	C12—H22	0.9800
C3—H7	0.9700	C13—H23	0.9700
C3—H8	0.9700	C13—H24	0.9700
C4—C5	1.515 (4)	C14—H25	0.9700
C4—H9	0.9700	C14—H26	0.9700
C4—H10	0.9700	C15—H27	0.9700
C5—C6	1.525 (4)	C15—H28	0.9700
C5—H11	0.9800	O1—H29	0.855 (11)
C6—C15	1.524 (4)	O1—H30	0.851 (11)

Cl4—Zn1—Cl2	116.81 (3)	C13—C7—C12	111.7 (2)
Cl4—Zn1—Cl3	110.69 (3)	C15—C7—C12	111.6 (2)
Cl2—Zn1—Cl3	107.54 (3)	C13—C7—H13	108.0
Cl4—Zn1—Cl1	110.06 (3)	C15—C7—H13	108.0
Cl2—Zn1—Cl1	103.57 (3)	C12—C7—H13	108.0
Cl3—Zn1—Cl1	107.60 (3)	N2—C8—C9	110.9 (3)
C13—N1—C5	113.2 (2)	N2—C8—H14	109.5
C13—N1—C1	110.3 (2)	C9—C8—H14	109.5
C5—N1—C1	110.28 (19)	N2—C8—H15	109.5
C13—N1—H1	107.6	C9—C8—H15	109.5
C5—N1—H1	107.6	H14—C8—H15	108.0
C1—N1—H1	107.6	C8—C9—C10	111.6 (3)
C14—N2—C8	109.7 (2)	C8—C9—H16	109.3
C14—N2—C12	112.65 (19)	C10—C9—H16	109.3
C8—N2—C12	111.4 (2)	C8—C9—H17	109.3
C14—N2—H2	107.6	C10—C9—H17	109.3
C8—N2—H2	107.6	H16—C9—H17	108.0
C12—N2—H2	107.6	C9—C10—C11	110.9 (3)
C2—C1—N1	110.5 (2)	C9—C10—H18	109.5
C2—C1—H3	109.5	C11—C10—H18	109.5
N1—C1—H3	109.5	C9—C10—H19	109.5
C2—C1—H4	109.5	C11—C10—H19	109.5
N1—C1—H4	109.5	H18—C10—H19	108.0
H3—C1—H4	108.1	C12—C11—C10	111.7 (3)
C1—C2—C3	111.1 (3)	C12—C11—H20	109.3
C1—C2—H5	109.4	C10—C11—H20	109.3
C3—C2—H5	109.4	C12—C11—H21	109.3
C1—C2—H6	109.4	C10—C11—H21	109.3
C3—C2—H6	109.4	H20—C11—H21	107.9
H5—C2—H6	108.0	N2—C12—C11	108.9 (2)
C4—C3—C2	111.1 (2)	N2—C12—C7	110.1 (2)
C4—C3—H7	109.4	C11—C12—C7	113.3 (2)
C2—C3—H7	109.4	N2—C12—H22	108.1
C4—C3—H8	109.4	C11—C12—H22	108.1
C2—C3—H8	109.4	C7—C12—H22	108.1
H7—C3—H8	108.0	N1—C13—C7	112.95 (19)
C5—C4—C3	112.3 (2)	N1—C13—H23	109.0
C5—C4—H9	109.1	C7—C13—H23	109.0
C3—C4—H9	109.1	N1—C13—H24	109.0
C5—C4—H10	109.1	C7—C13—H24	109.0
C3—C4—H10	109.1	H23—C13—H24	107.8
H9—C4—H10	107.9	N2—C14—C6	112.5 (2)
C4—C5—N1	108.5 (2)	N2—C14—H25	109.1
C4—C5—C6	114.8 (2)	C6—C14—H25	109.1
N1—C5—C6	111.49 (19)	N2—C14—H26	109.1
C4—C5—H11	107.2	C6—C14—H26	109.1
N1—C5—H11	107.2	H25—C14—H26	107.8
C6—C5—H11	107.2	C6—C15—C7	106.6 (2)
C15—C6—C5	109.6 (2)	C6—C15—H27	110.4
C15—C6—C14	109.9 (2)	C7—C15—H27	110.4
C5—C6—C14	114.7 (2)	C6—C15—H28	110.4
C15—C6—H12	107.4	C7—C15—H28	110.4
C5—C6—H12	107.4	H27—C15—H28	108.6
C14—C6—H12	107.4	H29—O1—H30	102 (2)
C13—C7—C15	109.3 (2)

C13—N1—C1—C2	−173.4 (2)	C8—N2—C12—C11	58.7 (3)
C5—N1—C1—C2	60.8 (3)	C14—N2—C12—C7	−52.7 (3)
N1—C1—C2—C3	−56.3 (3)	C8—N2—C12—C7	−176.5 (2)
C1—C2—C3—C4	52.9 (4)	C10—C11—C12—N2	−57.3 (3)
C2—C3—C4—C5	−54.1 (4)	C10—C11—C12—C7	179.8 (3)
C3—C4—C5—N1	57.4 (3)	C13—C7—C12—N2	119.0 (2)
C3—C4—C5—C6	−177.1 (2)	C15—C7—C12—N2	−3.8 (3)
C13—N1—C5—C4	175.8 (2)	C13—C7—C12—C11	−118.8 (3)
C1—N1—C5—C4	−60.1 (3)	C15—C7—C12—C11	118.5 (3)
C13—N1—C5—C6	48.4 (3)	C5—N1—C13—C7	−48.2 (3)
C1—N1—C5—C6	172.5 (2)	C1—N1—C13—C7	−172.3 (2)
C4—C5—C6—C15	178.6 (2)	C15—C7—C13—N1	56.2 (3)
N1—C5—C6—C15	−57.6 (3)	C12—C7—C13—N1	−67.9 (3)
C4—C5—C6—C14	−57.2 (3)	C8—N2—C14—C6	176.1 (2)
N1—C5—C6—C14	66.6 (3)	C12—N2—C14—C6	51.3 (3)
C14—N2—C8—C9	176.5 (3)	C15—C6—C14—N2	7.5 (3)
C12—N2—C8—C9	−58.0 (3)	C5—C6—C14—N2	−116.5 (3)
N2—C8—C9—C10	54.9 (4)	C5—C6—C15—C7	65.0 (3)
C8—C9—C10—C11	−53.4 (5)	C14—C6—C15—C7	−62.0 (3)
C9—C10—C11—C12	55.3 (4)	C13—C7—C15—C6	−63.8 (3)
C14—N2—C12—C11	−177.5 (2)	C12—C7—C15—C6	60.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.98	2.31	3.279 (2)	170
N2—H2···O1ⁱⁱ	0.98	1.83	2.798 (3)	168
O1—H30···Cl2ⁱ	0.85 (1)	2.71 (4)	3.355 (3)	133 (4)
O1—H30···Cl3ⁱ	0.85 (1)	2.76 (3)	3.473 (3)	143 (4)
O1—H29···Cl1ⁱⁱⁱ	0.86 (1)	2.42 (1)	3.257 (3)	167 (4)

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

Acknowledgements

SB acknowledges support by Instituto de Física Luis Rivera Terrazas (Puebla, Mexico).

References

Alcántara-Flores, J. L., Arias-López, N., Bernès, S., Gutiérrez, R. & Reyes Ortega, Y. (2009). Acta Cryst. E65, m1142–m1143. CSD CrossRef IUCr Journals Google Scholar
Bruker (1997). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Garnovskii, A. D., Kharisov, B. I., Gojon-Zorrilla, G. & Garnovskii, D. A. (1995). Russ. Chem. Rev. 64, 201–221. CrossRef Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hoppe, D. & Hense, T. (1997). Angew. Chem. Int. Ed. Engl. 36, 2282–2316. CrossRef CAS Google Scholar
Jasiewicz, B., Boczoń, W., Muth, D., Warżajtis, B., Rychlewska, U., Andrzejewski, B. & Toliński, T. (2006). J. Mol. Struct. 794, 311–319. CSD CrossRef CAS Google Scholar
Lee, Y.-M., Park, S.-M., Kang, S. K., Kim, Y.-I. & Choi, S.-N. (2004). Bull. Korean Chem. Soc. 25, 823–828. CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Okuniewski, A., Rosiak, D., Chojnacki, J. & Becker, B. (2015). Polyhedron, 90, 47–57. Web of Science CSD CrossRef CAS Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Streb, C., Long, D.-L. & Cronin, L. (2007). Chem. Commun. pp. 471–473. CSD CrossRef Google Scholar

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.