organic compounds
of 4,4′,4′′-(1,3,5-triazine-2,4,6-triyl)tripyridinium trichloride 2.5-hydrate
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
The 18H15N63+·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.
of the title compound, CKeywords: 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 of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (TPT), see: Janczak et al. (2003). For the of (1,3,5-triazine-2,4,6-triyl)tripyridinium nitrate, see: Zhu et al. (2007).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrysAlis PRO (Agilent, 2014); cell 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
https://doi.org/10.1107/S2056989015018125/xu5874sup1.cif
contains datablocks I, global. DOI: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
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 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.
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.
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 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.
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
of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (TPT), see: Janczak et al. (2003). For the of (1,3,5-triazine-2,4,6-triyl)tripyridinium nitrate, see: Zhu et al. (2007).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.
detailsAll 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 Uiso(H) = 1.2Ueq(C), Uiso(H) = 1.2Ueq(N). H atoms belonging to H2O groups were located in difference Fourier maps and refined isotropically.
Data collection: CrysAlis PRO (Agilent, 2014); cell
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).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. |
2C18H15N63+·6Cl−·5H2O | F(000) = 1928 |
Mr = 933.50 | Dx = 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 |
Agilent Xcalibur Atlas Gemini ultra diffractometer | 6654 reflections with I > 2σ(I) |
Detector resolution: 10.5058 pixels mm-1 | Rint = 0.020 |
ω scans | θmax = 65.6°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −12→12 |
Tmin = 0.575, Tmax = 1.000 | k = −11→16 |
27170 measured reflections | l = −32→31 |
7278 independent reflections |
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(Fo2) + (0.0455P)2 + 1.0459P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
7278 reflections | Δρmax = 0.26 e Å−3 |
572 parameters | Δρmin = −0.25 e Å−3 |
2C18H15N63+·6Cl−·5H2O | V = 4270.44 (7) Å3 |
Mr = 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)° |
Agilent Xcalibur Atlas Gemini ultra diffractometer | 7278 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | 6654 reflections with I > 2σ(I) |
Tmin = 0.575, Tmax = 1.000 | Rint = 0.020 |
27170 measured reflections |
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 | Δρmax = 0.26 e Å−3 |
7278 reflections | Δρmin = −0.25 e Å−3 |
572 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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) |
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···Cl01iv | 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···Cl02iv | 0.86 | 2.25 | 3.0732 (12) | 159 |
N9—H09···Cl02 | 0.86 | 2.19 | 3.0337 (12) | 166 |
C1—H1···Cl03v | 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···Cl06v | 0.93 | 2.70 | 3.4071 (15) | 134 |
C10—H10···O4 | 0.93 | 2.54 | 3.370 (2) | 148 |
C11—H11···Cl02vi | 0.93 | 2.61 | 3.5114 (15) | 163 |
C12—H12···Cl04 | 0.93 | 2.64 | 3.4992 (15) | 154 |
C15—H15···Cl03vii | 0.93 | 2.54 | 3.3157 (16) | 141 |
C21—H21···Cl05 | 0.93 | 2.74 | 3.5424 (15) | 146 |
C22—H22···Cl06v | 0.93 | 2.72 | 3.3883 (15) | 130 |
C24—H24···Cl05viii | 0.93 | 2.63 | 3.4519 (15) | 147 |
C26—H26···Cl04ix | 0.93 | 2.53 | 3.3669 (15) | 149 |
C30—H30···O2x | 0.93 | 2.31 | 3.2331 (19) | 174 |
C31—H31···O2viii | 0.93 | 2.50 | 3.3320 (19) | 149 |
C34—H34···O1ix | 0.93 | 2.50 | 3.3706 (19) | 156 |
C35—H35···Cl01xi | 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. |
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···Cl01iv | 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···Cl02iv | 0.86 | 2.25 | 3.0732 (12) | 159 |
N9—H09···Cl02 | 0.86 | 2.19 | 3.0337 (12) | 166 |
C1—H1···Cl03v | 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···Cl06v | 0.93 | 2.70 | 3.4071 (15) | 134 |
C10—H10···O4 | 0.93 | 2.54 | 3.370 (2) | 148 |
C11—H11···Cl02vi | 0.93 | 2.61 | 3.5114 (15) | 163 |
C12—H12···Cl04 | 0.93 | 2.64 | 3.4992 (15) | 154 |
C15—H15···Cl03vii | 0.93 | 2.54 | 3.3157 (16) | 141 |
C21—H21···Cl05 | 0.93 | 2.74 | 3.5424 (15) | 146 |
C22—H22···Cl06v | 0.93 | 2.72 | 3.3883 (15) | 130 |
C24—H24···Cl05viii | 0.93 | 2.63 | 3.4519 (15) | 147 |
C26—H26···Cl04ix | 0.93 | 2.53 | 3.3669 (15) | 149 |
C30—H30···O2x | 0.93 | 2.31 | 3.2331 (19) | 174 |
C31—H31···O2viii | 0.93 | 2.50 | 3.3320 (19) | 149 |
C34—H34···O1ix | 0.93 | 2.50 | 3.3706 (19) | 156 |
C35—H35···Cl01xi | 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. |
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.
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