Crystal structure of 4,4′,4′′-(1,3,5-triazine-2,4,6-tri­yl)tripyridinium trichloride 2.5-hydrate

Ling, B.-K.; Feng, X.-L.; Li, Y.; Luan, T.-G.

doi:10.1107/S2056989015018125

organic compounds

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ISSN: 2056-9890

Volume 71| Part 11| November 2015| Pages o858-o859

https://doi.org/10.1107/S2056989015018125

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Crystal structure of 4,4′,4′′-(1,3,5-triazine-2,4,6-triyl)tripyridinium trichloride 2.5-hydrate

Bo-Kai Ling,^a Xiao-Long Feng,^b Yang Li ^b ^* and Tian-Gang Luan ^a

^aSchool of Marine Science, Sun Yat-Sen University, Guangzhou 510275, People's Republic of China, and ^bInstrumental Analysis and Research Center, Sun Yat-Sen University, Guangzhou 510275, People's Republic of China
^*Correspondence e-mail: liyang223@mail.sysu.edu.cn

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 18 September 2015; accepted 28 September 2015; online 17 October 2015)

The asymmetric unit of the title compound, C₁₈H₁₅N₆³⁺·3Cl⁻·2.5H₂O, contains two independent (1,3,5-triazine-2,4,6-triyl)tripyridinium cations. Both cations are approximately planar, the r.m.s. deviations of fitted non-H atoms being 0.045 and 0.051 Å. In the crystal, extensive O—H⋯Cl, O—H⋯O, N—H⋯Cl and N—H⋯O hydrogen bonds and weak C—H⋯Cl and C—H⋯O interactions link the organic cations, Cl⁻ anions and water molecules into a three-dimensional supramolecular architecture. π–π stacking between the pyridine rings of adjacent cations is also observed, the centroid-to-centroid distance being 3.7578 (8) Å.

Keywords: crystal structure; 1,3,5-triazine; trichloride; hydrogen bonding; π–π interactions.

CCDC reference: 1427933

1. Related literature

For applications of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine, see: Yoshizawa et al. (2006 ); Inokuma et al. (2011 , 2013 ). For the crystal structure of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (TPT), see: Janczak et al. (2003 ). For the crystal structure of (1,3,5-triazine-2,4,6-triyl)tripyridinium nitrate, see: Zhu et al. (2007 ).

2. Experimental

2.1. Crystal data

2C₁₈H₁₅N₆³⁺·6Cl⁻·5H₂O
M_r = 933.50
Monoclinic P 2₁ /c
a = 10.6042 (1) Å
b = 14.6447 (1) Å
c = 27.7906 (3) Å
β = 98.310 (1)°
V = 4270.44 (7) Å³
Z = 4
Cu Kα radiation
μ = 4.15 mm⁻¹
T = 150 K
0.50 × 0.20 × 0.10 mm

2.2. Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ) T_min = 0.575, T_max = 1.000
27170 measured reflections
7278 independent reflections
6654 reflections with I > 2σ(I)
R_int = 0.020

2.3. Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.076
S = 1.05
7278 reflections
572 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl03ⁱ	0.77 (2)	2.47 (2)	3.2302 (15)	171 (2)
O1—H1B⋯Cl04	0.87 (2)	2.32 (2)	3.1856 (14)	175 (2)
O2—H2A⋯Cl04	0.86 (2)	2.28 (2)	3.1124 (15)	163.2 (18)
O2—H2B⋯Cl05	0.84 (2)	2.22 (2)	3.0515 (13)	170 (2)
O3—H3A⋯Cl06ⁱⁱ	0.84 (2)	2.22 (2)	3.0379 (13)	164.5 (18)
O3—H3B⋯O2	0.84 (2)	1.91 (2)	2.7426 (17)	176 (2)
O4—H4A⋯Cl05ⁱⁱⁱ	0.78 (2)	2.36 (2)	3.1356 (15)	172 (2)
O4—H4B⋯Cl03	0.83 (3)	2.47 (3)	3.2626 (14)	162 (3)
O5—H5A⋯Cl06	0.92 (2)	2.12 (2)	2.9973 (12)	157.4 (17)
O5—H5B⋯Cl03	0.81 (2)	2.24 (2)	3.0466 (12)	173 (2)
N1—H01⋯Cl01^iv	0.86	2.24	3.0678 (12)	161
N2—H02⋯O5	0.86	1.77	2.5985 (16)	162
N3—H03⋯Cl01	0.86	2.23	3.0405 (12)	158
N7—H07⋯O3	0.86	1.84	2.6472 (16)	155
N8—H08⋯Cl02^iv	0.86	2.25	3.0732 (12)	159
N9—H09⋯Cl02	0.86	2.19	3.0337 (12)	166
C1—H1⋯Cl03^v	0.93	2.57	3.4995 (15)	174
C4—H4⋯Cl04	0.93	2.61	3.4871 (14)	157
C5—H5⋯O1	0.93	2.38	3.2614 (19)	158
C9—H9⋯Cl06^v	0.93	2.70	3.4071 (15)	134
C10—H10⋯O4	0.93	2.54	3.370 (2)	148
C11—H11⋯Cl02^vi	0.93	2.61	3.5114 (15)	163
C12—H12⋯Cl04	0.93	2.64	3.4992 (15)	154
C15—H15⋯Cl03^vii	0.93	2.54	3.3157 (16)	141
C21—H21⋯Cl05	0.93	2.74	3.5424 (15)	146
C22—H22⋯Cl06^v	0.93	2.72	3.3883 (15)	130
C24—H24⋯Cl05^viii	0.93	2.63	3.4519 (15)	147
C26—H26⋯Cl04^ix	0.93	2.53	3.3669 (15)	149
C30—H30⋯O2^x	0.93	2.31	3.2331 (19)	174
C31—H31⋯O2^viii	0.93	2.50	3.3320 (19)	149
C34—H34⋯O1^ix	0.93	2.50	3.3706 (19)	156
C35—H35⋯Cl01^xi	0.93	2.72	3.6254 (14)	166
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) x-1, y, z; (iv) x, y-1, z; (v) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (vii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (viii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ix) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (x) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (xi) $[x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1427933

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989015018125/xu5874sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015018125/xu5874Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015018125/xu5874Isup3.cml

checkCIF report

Comment top

2,4,6-Tris(4-pyridyl)-1,3,5-triazine (TPT), as a planar tridentate ligand for MOFs (metal-organic frameworks), has been designed for some useful crystals by reactions with metal ions. Due to its special triazine π–π interaction, triangular plane geometry and tridentate N atoms coordinate, these crystals remarkable applications were discovered gradually such as molecular flask (Yoshizawa & Fujita, 2006; Inokuma & Fujita, 2011) and X-ray single-crystal diffraction carrier (Inokuma & Fujita, 2013). The crystal structure of neutral tpt was reported by (Janczak & Kubiak, 2003). The nitrate salt of TPT was published by Zhu (Zhu et al. 2007).

The crystal has a well layered form through π-π interaction and Hydrogen Bonds which is analogous to pure TPT crystal (Janczak & Kubiak, 2003). In the crystal, every pyridine has protonized. H₃TPT, Cl^- and H₂O pack in a layer through ionic bonding and hydrogen-bonding.

Synthesis and crystallization top

Excess hydrochloric acid (2 mL) was added in pure TPT (93mg, 0.3mmol) in a 20 mL scintillation vial. With the dropwise addition of hydrochloric acid, solution was clear gradually. Then the mixture was put in an oven at 393K for 10h. The colourless crystal will be found.

Refinement top

All H atoms for C and N atoms were geometrically fixed and allowed to ride on their parent C and N atoms, with C–H = 0.93 Å, N–H = 0.86 Å) and with U_iso(H) = 1.2U_eq(C), U_iso(H) = 1.2U_eq(N). H atoms belonging to H₂O groups were located in difference Fourier maps and refined isotropically.

Related literature top

For applications of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine, see: Yoshizawa et al. (2006); Inokuma et al. (2011, 2013). For the crystal structure of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (TPT), see: Janczak et al. (2003). For the crystal structure of (1,3,5-triazine-2,4,6-triyl)tripyridinium nitrate, see: Zhu et al. (2007).

Structure description top

For applications of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine, see: Yoshizawa et al. (2006); Inokuma et al. (2011, 2013). For the crystal structure of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (TPT), see: Janczak et al. (2003). For the crystal structure of (1,3,5-triazine-2,4,6-triyl)tripyridinium nitrate, see: Zhu et al. (2007).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the b axis. Colour key: red indicates oxygen and green chlorine.

4,4',4''-(1,3,5-Triazine-2,4,6-triyl)tripyridinium trichloride 2.5-hydrate top

Crystal data top

2C₁₈H₁₅N₆³⁺·6Cl⁻·5H₂O	F(000) = 1928
M_r = 933.50	D_x = 1.452 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 10.6042 (1) Å	Cell parameters from 15012 reflections
b = 14.6447 (1) Å	θ = 3.0–65.5°
c = 27.7906 (3) Å	µ = 4.15 mm⁻¹
β = 98.310 (1)°	T = 150 K
V = 4270.44 (7) Å³	Rod, colourless
Z = 4	0.50 × 0.20 × 0.10 mm

Data collection top

Agilent Xcalibur Atlas Gemini ultra diffractometer	6654 reflections with I > 2σ(I)
Detector resolution: 10.5058 pixels mm^-1	R_int = 0.020
ω scans	θ_max = 65.6°, θ_min = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −12→12
T_min = 0.575, T_max = 1.000	k = −11→16
27170 measured reflections	l = −32→31
7278 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0455P)² + 1.0459P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.002
7278 reflections	Δρ_max = 0.26 e Å⁻³
572 parameters	Δρ_min = −0.25 e Å⁻³

Crystal data top

2C₁₈H₁₅N₆³⁺·6Cl⁻·5H₂O	V = 4270.44 (7) Å³
M_r = 933.50	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.6042 (1) Å	µ = 4.15 mm⁻¹
b = 14.6447 (1) Å	T = 150 K
c = 27.7906 (3) Å	0.50 × 0.20 × 0.10 mm
β = 98.310 (1)°

Data collection top

Agilent Xcalibur Atlas Gemini ultra diffractometer	7278 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	6654 reflections with I > 2σ(I)
T_min = 0.575, T_max = 1.000	R_int = 0.020
27170 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.26 e Å⁻³
7278 reflections	Δρ_min = −0.25 e Å⁻³
572 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Cl01	0.65529 (3)	0.87819 (2)	0.53046 (2)	0.02080 (9)
Cl02	−0.15165 (3)	0.86725 (2)	0.96259 (2)	0.02038 (9)
Cl03	−0.30029 (3)	0.33680 (2)	0.86906 (2)	0.02704 (9)
Cl04	0.76231 (3)	0.34758 (2)	0.52883 (2)	0.02860 (10)
Cl05	0.69917 (4)	0.19615 (3)	0.70100 (2)	0.03228 (10)
Cl06	−0.24393 (4)	0.61127 (3)	0.75183 (2)	0.03989 (12)
O5	−0.13385 (10)	0.45402 (8)	0.81302 (4)	0.0293 (2)
O3	0.65114 (11)	0.45593 (9)	0.68539 (4)	0.0292 (2)
O2	0.80923 (11)	0.34430 (8)	0.64199 (5)	0.0308 (2)
O1	0.79029 (12)	0.14892 (9)	0.48489 (5)	0.0349 (3)
N11	0.05285 (10)	0.36030 (8)	0.90020 (4)	0.0181 (2)
N10	0.20086 (10)	0.29011 (7)	0.85541 (4)	0.0189 (2)
N6	0.46303 (11)	0.37119 (8)	0.59643 (4)	0.0193 (2)
N5	0.33219 (11)	0.46467 (8)	0.63822 (4)	0.0199 (2)
O4	−0.13673 (13)	0.20960 (9)	0.80408 (5)	0.0434 (3)
N4	0.32306 (11)	0.30340 (8)	0.64532 (4)	0.0204 (2)
N12	0.18691 (10)	0.45145 (8)	0.85844 (4)	0.0190 (2)
N9	−0.06099 (11)	0.67836 (8)	0.93866 (4)	0.0226 (3)
H09	−0.0926	0.7271	0.9494	0.027*
N3	0.57300 (11)	0.68432 (8)	0.54975 (4)	0.0229 (3)
H03	0.6040	0.7318	0.5375	0.027*
N1	0.52800 (11)	0.03964 (8)	0.57480 (4)	0.0224 (3)
H01	0.5519	−0.0134	0.5663	0.027*
N8	−0.00911 (11)	0.02831 (8)	0.92431 (4)	0.0225 (3)
H08	−0.0319	−0.0247	0.9332	0.027*
N7	0.51720 (11)	0.39554 (9)	0.75219 (4)	0.0251 (3)
H07	0.5727	0.4001	0.7326	0.030*
N2	0.00613 (11)	0.41058 (9)	0.74708 (4)	0.0268 (3)
H02	−0.0498	0.4151	0.7665	0.032*
C16	0.41129 (12)	0.29914 (9)	0.61556 (5)	0.0181 (3)
C36	0.23658 (12)	0.37382 (9)	0.84431 (5)	0.0173 (3)
C37	0.10782 (12)	0.28751 (9)	0.88325 (5)	0.0164 (3)
C17	0.28607 (13)	0.38778 (9)	0.65473 (5)	0.0186 (3)
C38	0.09613 (12)	0.44037 (9)	0.88672 (5)	0.0171 (3)
C23	0.33836 (13)	0.38155 (9)	0.81286 (5)	0.0191 (3)
C18	0.42064 (12)	0.45195 (9)	0.60929 (5)	0.0183 (3)
C33	0.04010 (12)	0.52483 (9)	0.90481 (5)	0.0181 (3)
C28	0.06487 (12)	0.19579 (9)	0.89691 (5)	0.0179 (3)
C34	−0.04614 (13)	0.51835 (9)	0.93800 (5)	0.0206 (3)
H34	−0.0701	0.4616	0.9486	0.025*
C8	0.18526 (13)	0.39663 (10)	0.68655 (5)	0.0203 (3)
C3	0.45303 (12)	0.20713 (9)	0.60187 (5)	0.0190 (3)
C12	0.56434 (13)	0.52499 (10)	0.55698 (5)	0.0211 (3)
H12	0.5915	0.4673	0.5490	0.025*
C22	0.39093 (13)	0.30344 (10)	0.79539 (5)	0.0221 (3)
H22	0.3655	0.2459	0.8043	0.027*
C4	0.54831 (13)	0.19906 (9)	0.57262 (5)	0.0204 (3)
H4	0.5869	0.2509	0.5620	0.025*
C27	−0.02943 (13)	0.18762 (9)	0.92639 (5)	0.0214 (3)
H27	−0.0680	0.2394	0.9371	0.026*
C13	0.47470 (12)	0.53481 (9)	0.58865 (5)	0.0189 (3)
C2	0.39638 (14)	0.12860 (10)	0.61731 (5)	0.0232 (3)
H2	0.3332	0.1329	0.6372	0.028*
C9	0.13433 (13)	0.31852 (10)	0.70484 (5)	0.0236 (3)
H9	0.1610	0.2609	0.6965	0.028*
C7	0.14280 (14)	0.48231 (10)	0.69901 (5)	0.0250 (3)
H7	0.1751	0.5352	0.6868	0.030*
C31	0.02052 (14)	0.68671 (10)	0.90647 (5)	0.0244 (3)
H31	0.0416	0.7444	0.8961	0.029*
C5	0.58482 (13)	0.11328 (10)	0.55959 (5)	0.0227 (3)
H5	0.6489	0.1068	0.5402	0.027*
C11	0.61224 (13)	0.60190 (10)	0.53762 (5)	0.0230 (3)
H11	0.6716	0.5965	0.5162	0.028*
C24	0.37914 (13)	0.46732 (10)	0.79972 (5)	0.0232 (3)
H24	0.3456	0.5202	0.8114	0.028*
C29	0.11984 (14)	0.11722 (9)	0.88081 (5)	0.0233 (3)
H29	0.1817	0.1215	0.8603	0.028*
C1	0.43502 (14)	0.04472 (10)	0.60282 (5)	0.0250 (3)
H1	0.3971	−0.0083	0.6124	0.030*
C26	−0.06542 (14)	0.10175 (10)	0.93967 (5)	0.0240 (3)
H26	−0.1288	0.0952	0.9593	0.029*
C30	0.08193 (14)	0.03369 (10)	0.89543 (5)	0.0265 (3)
H30	0.1190	−0.0192	0.8854	0.032*
C32	0.07329 (13)	0.61014 (9)	0.88867 (5)	0.0224 (3)
H32	0.1301	0.6154	0.8663	0.027*
C35	−0.09538 (13)	0.59728 (10)	0.95483 (5)	0.0231 (3)
H35	−0.1522	0.5943	0.9773	0.028*
C25	0.47006 (14)	0.47203 (10)	0.76910 (5)	0.0261 (3)
H25	0.4989	0.5286	0.7601	0.031*
C6	0.05204 (14)	0.48706 (11)	0.72970 (5)	0.0288 (3)
H6	0.0225	0.5436	0.7384	0.035*
C14	0.43625 (14)	0.62155 (10)	0.60020 (6)	0.0252 (3)
H14	0.3764	0.6292	0.6213	0.030*
C15	0.48771 (14)	0.69618 (10)	0.58015 (6)	0.0267 (3)
H15	0.4632	0.7548	0.5877	0.032*
C21	0.48130 (14)	0.31252 (10)	0.76462 (5)	0.0256 (3)
H21	0.5171	0.2609	0.7526	0.031*
C10	0.04389 (14)	0.32775 (11)	0.73544 (5)	0.0269 (3)
H10	0.0092	0.2762	0.7480	0.032*
H3A	0.6891 (18)	0.5011 (15)	0.6995 (7)	0.040 (5)*
H2A	0.7816 (19)	0.3391 (13)	0.6115 (8)	0.042 (6)*
H5A	−0.1779 (18)	0.5060 (14)	0.8017 (7)	0.042 (5)*
H5B	−0.183 (2)	0.4236 (15)	0.8260 (8)	0.048 (6)*
H3B	0.7020 (19)	0.4219 (14)	0.6736 (7)	0.041 (5)*
H1A	0.761 (2)	0.1505 (14)	0.4580 (8)	0.044 (6)*
H1B	0.784 (2)	0.2044 (17)	0.4950 (8)	0.054 (6)*
H2B	0.780 (2)	0.2994 (16)	0.6554 (8)	0.058 (7)*
H4A	−0.184 (2)	0.2070 (14)	0.7798 (8)	0.047 (6)*
H4B	−0.187 (3)	0.2301 (19)	0.8215 (10)	0.081 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl01	0.02249 (17)	0.01723 (17)	0.02277 (17)	−0.00011 (12)	0.00355 (13)	−0.00023 (12)
Cl02	0.02001 (16)	0.01681 (16)	0.02501 (17)	0.00094 (12)	0.00562 (13)	0.00004 (12)
Cl03	0.02599 (18)	0.02703 (19)	0.02979 (19)	−0.00023 (14)	0.00972 (14)	0.00424 (14)
Cl04	0.03331 (19)	0.02561 (19)	0.03073 (19)	0.00059 (14)	0.01765 (15)	0.00042 (14)
Cl05	0.0433 (2)	0.0277 (2)	0.02738 (19)	−0.00284 (16)	0.01019 (16)	−0.00100 (14)
Cl06	0.0475 (3)	0.0177 (2)	0.0515 (3)	0.00120 (15)	−0.0030 (2)	0.00063 (15)
O5	0.0277 (6)	0.0328 (6)	0.0302 (6)	0.0034 (5)	0.0133 (5)	0.0089 (5)
O3	0.0305 (6)	0.0310 (6)	0.0284 (6)	−0.0026 (5)	0.0117 (5)	−0.0055 (5)
O2	0.0363 (6)	0.0271 (6)	0.0311 (6)	−0.0062 (5)	0.0117 (5)	−0.0014 (5)
O1	0.0458 (7)	0.0299 (7)	0.0313 (7)	0.0061 (5)	0.0130 (6)	−0.0008 (5)
N11	0.0168 (5)	0.0166 (6)	0.0207 (6)	0.0013 (4)	0.0023 (4)	0.0007 (4)
N10	0.0193 (6)	0.0178 (6)	0.0200 (6)	−0.0003 (4)	0.0041 (4)	−0.0017 (4)
N6	0.0177 (5)	0.0182 (6)	0.0223 (6)	−0.0009 (4)	0.0040 (5)	−0.0013 (5)
N5	0.0196 (6)	0.0209 (6)	0.0200 (6)	0.0002 (5)	0.0058 (4)	−0.0012 (5)
O4	0.0417 (7)	0.0501 (8)	0.0365 (7)	0.0121 (6)	−0.0004 (6)	−0.0063 (6)
N4	0.0207 (6)	0.0205 (6)	0.0204 (6)	0.0020 (5)	0.0043 (5)	0.0019 (5)
N12	0.0197 (6)	0.0176 (6)	0.0202 (6)	0.0011 (4)	0.0044 (4)	−0.0004 (4)
N9	0.0227 (6)	0.0178 (6)	0.0277 (6)	0.0037 (5)	0.0053 (5)	−0.0045 (5)
N3	0.0235 (6)	0.0177 (6)	0.0280 (6)	−0.0024 (5)	0.0060 (5)	0.0029 (5)
N1	0.0266 (6)	0.0159 (6)	0.0241 (6)	0.0045 (5)	0.0018 (5)	−0.0009 (5)
N8	0.0291 (6)	0.0159 (6)	0.0228 (6)	−0.0031 (5)	0.0053 (5)	0.0019 (5)
N7	0.0201 (6)	0.0362 (7)	0.0204 (6)	−0.0038 (5)	0.0077 (5)	−0.0024 (5)
N2	0.0217 (6)	0.0391 (7)	0.0214 (6)	0.0031 (5)	0.0095 (5)	0.0048 (5)
C16	0.0168 (6)	0.0188 (7)	0.0182 (6)	−0.0002 (5)	0.0010 (5)	0.0011 (5)
C36	0.0170 (6)	0.0185 (7)	0.0163 (6)	−0.0004 (5)	0.0021 (5)	0.0000 (5)
C37	0.0152 (6)	0.0180 (7)	0.0157 (6)	0.0001 (5)	0.0007 (5)	−0.0001 (5)
C17	0.0183 (6)	0.0198 (7)	0.0176 (6)	0.0013 (5)	0.0021 (5)	0.0010 (5)
C38	0.0161 (6)	0.0181 (7)	0.0170 (6)	0.0000 (5)	0.0018 (5)	0.0007 (5)
C23	0.0172 (6)	0.0228 (7)	0.0171 (6)	−0.0013 (5)	0.0019 (5)	−0.0023 (5)
C18	0.0168 (6)	0.0185 (7)	0.0192 (6)	0.0002 (5)	0.0016 (5)	−0.0010 (5)
C33	0.0170 (6)	0.0169 (7)	0.0198 (6)	0.0002 (5)	0.0014 (5)	−0.0014 (5)
C28	0.0172 (6)	0.0193 (7)	0.0164 (6)	0.0010 (5)	−0.0002 (5)	−0.0002 (5)
C34	0.0208 (7)	0.0181 (7)	0.0238 (7)	−0.0007 (5)	0.0070 (5)	0.0013 (5)
C8	0.0186 (7)	0.0252 (7)	0.0171 (6)	0.0023 (6)	0.0025 (5)	0.0015 (5)
C3	0.0175 (6)	0.0195 (7)	0.0191 (6)	0.0004 (5)	−0.0002 (5)	−0.0001 (5)
C12	0.0216 (7)	0.0188 (7)	0.0236 (7)	0.0015 (5)	0.0064 (6)	−0.0017 (5)
C22	0.0217 (7)	0.0228 (7)	0.0222 (7)	−0.0015 (6)	0.0042 (6)	−0.0025 (6)
C4	0.0205 (7)	0.0196 (7)	0.0212 (7)	−0.0009 (5)	0.0031 (5)	−0.0008 (5)
C27	0.0247 (7)	0.0181 (7)	0.0224 (7)	0.0019 (6)	0.0071 (6)	−0.0002 (5)
C13	0.0178 (6)	0.0190 (7)	0.0198 (7)	−0.0007 (5)	0.0025 (5)	−0.0007 (5)
C2	0.0216 (7)	0.0228 (7)	0.0260 (7)	0.0005 (6)	0.0059 (6)	0.0025 (6)
C9	0.0234 (7)	0.0250 (8)	0.0228 (7)	0.0008 (6)	0.0046 (6)	0.0034 (6)
C7	0.0265 (7)	0.0237 (8)	0.0262 (7)	0.0024 (6)	0.0088 (6)	0.0039 (6)
C31	0.0249 (7)	0.0172 (7)	0.0317 (8)	−0.0013 (6)	0.0065 (6)	0.0014 (6)
C5	0.0216 (7)	0.0247 (7)	0.0219 (7)	0.0019 (6)	0.0036 (6)	−0.0015 (6)
C11	0.0218 (7)	0.0243 (7)	0.0240 (7)	0.0003 (6)	0.0075 (6)	−0.0008 (6)
C24	0.0240 (7)	0.0232 (7)	0.0235 (7)	−0.0024 (6)	0.0067 (6)	−0.0022 (6)
C29	0.0230 (7)	0.0202 (7)	0.0282 (8)	0.0005 (6)	0.0094 (6)	−0.0007 (6)
C1	0.0269 (7)	0.0191 (7)	0.0290 (8)	−0.0007 (6)	0.0040 (6)	0.0035 (6)
C26	0.0265 (7)	0.0238 (7)	0.0230 (7)	−0.0016 (6)	0.0083 (6)	−0.0004 (6)
C30	0.0301 (8)	0.0182 (7)	0.0328 (8)	0.0024 (6)	0.0100 (6)	−0.0027 (6)
C32	0.0222 (7)	0.0198 (7)	0.0269 (7)	−0.0009 (6)	0.0087 (6)	0.0005 (6)
C35	0.0225 (7)	0.0235 (7)	0.0246 (7)	0.0016 (6)	0.0075 (6)	−0.0008 (6)
C25	0.0269 (7)	0.0269 (8)	0.0255 (7)	−0.0051 (6)	0.0074 (6)	−0.0006 (6)
C6	0.0295 (8)	0.0309 (8)	0.0279 (8)	0.0079 (6)	0.0103 (6)	0.0009 (6)
C14	0.0253 (7)	0.0211 (7)	0.0319 (8)	0.0009 (6)	0.0129 (6)	−0.0016 (6)
C15	0.0280 (8)	0.0180 (7)	0.0360 (8)	0.0024 (6)	0.0116 (6)	−0.0019 (6)
C21	0.0230 (7)	0.0297 (8)	0.0245 (7)	0.0015 (6)	0.0053 (6)	−0.0068 (6)
C10	0.0239 (7)	0.0318 (8)	0.0261 (7)	−0.0002 (6)	0.0069 (6)	0.0066 (6)

Geometric parameters (Å, º) top

O5—H5A	0.92 (2)	C18—C13	1.4917 (19)
O5—H5B	0.81 (2)	C33—C32	1.3899 (19)
O3—H3A	0.84 (2)	C33—C34	1.3928 (19)
O3—H3B	0.84 (2)	C28—C27	1.3865 (19)
O2—H2A	0.86 (2)	C28—C29	1.3926 (19)
O2—H2B	0.84 (2)	C34—C35	1.378 (2)
O1—H1A	0.77 (2)	C34—H34	0.9300
O1—H1B	0.87 (2)	C8—C9	1.392 (2)
N11—C38	1.3325 (17)	C8—C7	1.393 (2)
N11—C37	1.3332 (17)	C3—C4	1.3904 (19)
N10—C36	1.3325 (17)	C3—C2	1.394 (2)
N10—C37	1.3395 (17)	C12—C11	1.377 (2)
N6—C18	1.3324 (17)	C12—C13	1.3932 (19)
N6—C16	1.3348 (17)	C12—H12	0.9300
N5—C18	1.3336 (17)	C22—C21	1.380 (2)
N5—C17	1.3350 (18)	C22—H22	0.9300
O4—H4A	0.78 (2)	C4—C5	1.378 (2)
O4—H4B	0.83 (3)	C4—H4	0.9300
N4—C17	1.3338 (18)	C27—C26	1.380 (2)
N4—C16	1.3369 (17)	C27—H27	0.9300
N12—C36	1.3355 (17)	C13—C14	1.386 (2)
N12—C38	1.3378 (17)	C2—C1	1.374 (2)
N9—C31	1.3364 (19)	C2—H2	0.9300
N9—C35	1.3387 (19)	C9—C10	1.377 (2)
N9—H09	0.8600	C9—H9	0.9300
N3—C15	1.3351 (19)	C7—C6	1.377 (2)
N3—C11	1.3359 (19)	C7—H7	0.9300
N3—H03	0.8600	C31—C32	1.377 (2)
N1—C5	1.3336 (19)	C31—H31	0.9300
N1—C1	1.3438 (19)	C5—H5	0.9300
N1—H01	0.8600	C11—H11	0.9300
N8—C26	1.3300 (19)	C24—C25	1.377 (2)
N8—C30	1.3439 (19)	C24—H24	0.9300
N8—H08	0.8600	C29—C30	1.368 (2)
N7—C21	1.334 (2)	C29—H29	0.9300
N7—C25	1.3393 (19)	C1—H1	0.9300
N7—H07	0.8600	C26—H26	0.9300
N2—C10	1.332 (2)	C30—H30	0.9300
N2—C6	1.339 (2)	C32—H32	0.9300
N2—H02	0.8600	C35—H35	0.9300
C16—C3	1.4848 (19)	C25—H25	0.9300
C36—C23	1.4880 (19)	C6—H6	0.9300
C37—C28	1.4852 (19)	C14—C15	1.375 (2)
C17—C8	1.4883 (19)	C14—H14	0.9300
C38—C33	1.4906 (18)	C15—H15	0.9300
C23—C22	1.390 (2)	C21—H21	0.9300
C23—C24	1.394 (2)	C10—H10	0.9300

H5A—O5—H5B	106.5 (19)	C21—C22—H22	120.4
H3A—O3—H3B	111.1 (19)	C23—C22—H22	120.4
H2A—O2—H2B	106 (2)	C5—C4—C3	119.11 (13)
H1A—O1—H1B	104 (2)	C5—C4—H4	120.4
C38—N11—C37	114.73 (11)	C3—C4—H4	120.4
C36—N10—C37	114.68 (11)	C26—C27—C28	119.19 (13)
C18—N6—C16	114.89 (11)	C26—C27—H27	120.4
C18—N5—C17	114.45 (11)	C28—C27—H27	120.4
H4A—O4—H4B	97 (2)	C14—C13—C12	119.43 (13)
C17—N4—C16	114.62 (11)	C14—C13—C18	120.95 (12)
C36—N12—C38	114.68 (11)	C12—C13—C18	119.61 (12)
C31—N9—C35	122.67 (12)	C1—C2—C3	119.19 (13)
C31—N9—H09	118.7	C1—C2—H2	120.4
C35—N9—H09	118.7	C3—C2—H2	120.4
C15—N3—C11	122.78 (12)	C10—C9—C8	119.09 (14)
C15—N3—H03	118.6	C10—C9—H9	120.5
C11—N3—H03	118.6	C8—C9—H9	120.5
C5—N1—C1	122.81 (12)	C6—C7—C8	118.64 (14)
C5—N1—H01	118.6	C6—C7—H7	120.7
C1—N1—H01	118.6	C8—C7—H7	120.7
C26—N8—C30	122.61 (12)	N9—C31—C32	120.12 (13)
C26—N8—H08	118.7	N9—C31—H31	119.9
C30—N8—H08	118.7	C32—C31—H31	119.9
C21—N7—C25	122.43 (12)	N1—C5—C4	119.79 (13)
C21—N7—H07	118.8	N1—C5—H5	120.1
C25—N7—H07	118.8	C4—C5—H5	120.1
C10—N2—C6	122.45 (12)	N3—C11—C12	119.64 (13)
C10—N2—H02	118.8	N3—C11—H11	120.2
C6—N2—H02	118.8	C12—C11—H11	120.2
N6—C16—N4	125.05 (12)	C25—C24—C23	118.58 (13)
N6—C16—C3	117.42 (12)	C25—C24—H24	120.7
N4—C16—C3	117.52 (12)	C23—C24—H24	120.7
N10—C36—N12	125.28 (12)	C30—C29—C28	119.28 (13)
N10—C36—C23	117.42 (11)	C30—C29—H29	120.4
N12—C36—C23	117.28 (11)	C28—C29—H29	120.4
N11—C37—N10	125.28 (12)	N1—C1—C2	119.62 (13)
N11—C37—C28	117.83 (11)	N1—C1—H1	120.2
N10—C37—C28	116.87 (11)	C2—C1—H1	120.2
N4—C17—N5	125.54 (12)	N8—C26—C27	119.79 (13)
N4—C17—C8	117.00 (12)	N8—C26—H26	120.1
N5—C17—C8	117.46 (12)	C27—C26—H26	120.1
N11—C38—N12	125.32 (12)	N8—C30—C29	119.81 (13)
N11—C38—C33	117.72 (11)	N8—C30—H30	120.1
N12—C38—C33	116.96 (11)	C29—C30—H30	120.1
C22—C23—C24	119.64 (13)	C31—C32—C33	118.76 (13)
C22—C23—C36	120.26 (12)	C31—C32—H32	120.6
C24—C23—C36	120.07 (12)	C33—C32—H32	120.6
N6—C18—N5	125.43 (12)	N9—C35—C34	119.68 (13)
N6—C18—C13	117.10 (11)	N9—C35—H35	120.2
N5—C18—C13	117.46 (12)	C34—C35—H35	120.2
C32—C33—C34	119.75 (12)	N7—C25—C24	120.35 (14)
C32—C33—C38	120.34 (12)	N7—C25—H25	119.8
C34—C33—C38	119.91 (12)	C24—C25—H25	119.8
C27—C28—C29	119.32 (13)	N2—C6—C7	120.29 (14)
C27—C28—C37	120.21 (12)	N2—C6—H6	119.9
C29—C28—C37	120.47 (12)	C7—C6—H6	119.9
C35—C34—C33	119.01 (13)	C15—C14—C13	119.17 (13)
C35—C34—H34	120.5	C15—C14—H14	120.4
C33—C34—H34	120.5	C13—C14—H14	120.4
C9—C8—C7	119.53 (13)	N3—C15—C14	119.86 (13)
C9—C8—C17	119.69 (12)	N3—C15—H15	120.1
C7—C8—C17	120.77 (12)	C14—C15—H15	120.1
C4—C3—C2	119.46 (13)	N7—C21—C22	119.86 (13)
C4—C3—C16	119.71 (12)	N7—C21—H21	120.1
C2—C3—C16	120.82 (12)	C22—C21—H21	120.1
C11—C12—C13	119.11 (13)	N2—C10—C9	120.00 (14)
C11—C12—H12	120.4	N2—C10—H10	120.0
C13—C12—H12	120.4	C9—C10—H10	120.0
C21—C22—C23	119.11 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl03ⁱ	0.77 (2)	2.47 (2)	3.2302 (15)	171 (2)
O1—H1B···Cl04	0.87 (2)	2.32 (2)	3.1856 (14)	175 (2)
O2—H2A···Cl04	0.86 (2)	2.28 (2)	3.1124 (15)	163.2 (18)
O2—H2B···Cl05	0.84 (2)	2.22 (2)	3.0515 (13)	170 (2)
O3—H3A···Cl06ⁱⁱ	0.84 (2)	2.22 (2)	3.0379 (13)	164.5 (18)
O3—H3B···O2	0.84 (2)	1.91 (2)	2.7426 (17)	176 (2)
O4—H4A···Cl05ⁱⁱⁱ	0.78 (2)	2.36 (2)	3.1356 (15)	172 (2)
O4—H4B···Cl03	0.83 (3)	2.47 (3)	3.2626 (14)	162 (3)
O5—H5A···Cl06	0.92 (2)	2.12 (2)	2.9973 (12)	157.4 (17)
O5—H5B···Cl03	0.81 (2)	2.24 (2)	3.0466 (12)	173 (2)
N1—H01···Cl01^iv	0.86	2.24	3.0678 (12)	161
N2—H02···O5	0.86	1.77	2.5985 (16)	162
N3—H03···Cl01	0.86	2.23	3.0405 (12)	158
N7—H07···O3	0.86	1.84	2.6472 (16)	155
N8—H08···Cl02^iv	0.86	2.25	3.0732 (12)	159
N9—H09···Cl02	0.86	2.19	3.0337 (12)	166
C1—H1···Cl03^v	0.93	2.57	3.4995 (15)	174
C4—H4···Cl04	0.93	2.61	3.4871 (14)	157
C5—H5···O1	0.93	2.38	3.2614 (19)	158
C9—H9···Cl06^v	0.93	2.70	3.4071 (15)	134
C10—H10···O4	0.93	2.54	3.370 (2)	148
C11—H11···Cl02^vi	0.93	2.61	3.5114 (15)	163
C12—H12···Cl04	0.93	2.64	3.4992 (15)	154
C15—H15···Cl03^vii	0.93	2.54	3.3157 (16)	141
C21—H21···Cl05	0.93	2.74	3.5424 (15)	146
C22—H22···Cl06^v	0.93	2.72	3.3883 (15)	130
C24—H24···Cl05^viii	0.93	2.63	3.4519 (15)	147
C26—H26···Cl04^ix	0.93	2.53	3.3669 (15)	149
C30—H30···O2^x	0.93	2.31	3.2331 (19)	174
C31—H31···O2^viii	0.93	2.50	3.3320 (19)	149
C34—H34···O1^ix	0.93	2.50	3.3706 (19)	156
C35—H35···Cl01^xi	0.93	2.72	3.6254 (14)	166

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl03ⁱ	0.77 (2)	2.47 (2)	3.2302 (15)	171 (2)
O1—H1B···Cl04	0.87 (2)	2.32 (2)	3.1856 (14)	175 (2)
O2—H2A···Cl04	0.86 (2)	2.28 (2)	3.1124 (15)	163.2 (18)
O2—H2B···Cl05	0.84 (2)	2.22 (2)	3.0515 (13)	170 (2)
O3—H3A···Cl06ⁱⁱ	0.84 (2)	2.22 (2)	3.0379 (13)	164.5 (18)
O3—H3B···O2	0.84 (2)	1.91 (2)	2.7426 (17)	176 (2)
O4—H4A···Cl05ⁱⁱⁱ	0.78 (2)	2.36 (2)	3.1356 (15)	172 (2)
O4—H4B···Cl03	0.83 (3)	2.47 (3)	3.2626 (14)	162 (3)
O5—H5A···Cl06	0.92 (2)	2.12 (2)	2.9973 (12)	157.4 (17)
O5—H5B···Cl03	0.81 (2)	2.24 (2)	3.0466 (12)	173 (2)
N1—H01···Cl01^iv	0.86	2.24	3.0678 (12)	161
N2—H02···O5	0.86	1.77	2.5985 (16)	162
N3—H03···Cl01	0.86	2.23	3.0405 (12)	158
N7—H07···O3	0.86	1.84	2.6472 (16)	155
N8—H08···Cl02^iv	0.86	2.25	3.0732 (12)	159
N9—H09···Cl02	0.86	2.19	3.0337 (12)	166
C1—H1···Cl03^v	0.93	2.57	3.4995 (15)	174
C4—H4···Cl04	0.93	2.61	3.4871 (14)	157
C5—H5···O1	0.93	2.38	3.2614 (19)	158
C9—H9···Cl06^v	0.93	2.70	3.4071 (15)	134
C10—H10···O4	0.93	2.54	3.370 (2)	148
C11—H11···Cl02^vi	0.93	2.61	3.5114 (15)	163
C12—H12···Cl04	0.93	2.64	3.4992 (15)	154
C15—H15···Cl03^vii	0.93	2.54	3.3157 (16)	141
C21—H21···Cl05	0.93	2.74	3.5424 (15)	146
C22—H22···Cl06^v	0.93	2.72	3.3883 (15)	130
C24—H24···Cl05^viii	0.93	2.63	3.4519 (15)	147
C26—H26···Cl04^ix	0.93	2.53	3.3669 (15)	149
C30—H30···O2^x	0.93	2.31	3.2331 (19)	174
C31—H31···O2^viii	0.93	2.50	3.3320 (19)	149
C34—H34···O1^ix	0.93	2.50	3.3706 (19)	156
C35—H35···Cl01^xi	0.93	2.72	3.6254 (14)	166

Acknowledgements

This research was supported financially by the National Natural Science Foundation of China (NSFC grants No. 21277177 and 41473092), the Foundation for High-level Talents in Higher Education of Guangdong Province and the Administration of Ocean and Fisheries of Guangdong Province, China.

References

Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Inokuma, Y., Kawano, M. & Fujita, M. (2011). Nat. Chem. 3, 349–358. Web of Science CrossRef CAS PubMed Google Scholar
Inokuma, Y., Yoshioka, S., Ariyoshi, J., Arai, T., Hitora, Y., Takada, K., Matsunaga, S., Rissanen, K. & Fujita, M. (2013). Nature, 495, 461–466. Web of Science CSD CrossRef CAS PubMed Google Scholar
Janczak, J., Śledź, M. & Kubiak, R. (2003). J. Mol. Struct. 659, 71–79. Web of Science CSD CrossRef CAS 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
Yoshizawa, M., Tamura, M. & Fujita, M. (2006). Science, 312, 251–254. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhu, S.-R., Chen, W.-D., Zhao, H.-J., Shao, M. & Li, M.-X. (2007). Acta Cryst. E63, o1344–o1346. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 71| Part 11| November 2015| Pages o858-o859

https://doi.org/10.1107/S2056989015018125

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

Crystal structure of 4,4′,4′′-(1,3,5-triazine-2,4,6-tri­yl)tripyridinium trichloride 2.5-hydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 4,4′,4′′-(1,3,5-triazine-2,4,6-triyl)tripyridinium trichloride 2.5-hydrate