organic compounds
4-Amino-N-(2,3-dihydro-1,3-thiazol-2-ylidene)benzenesulfonamide–2,4,6-tris(pyridin-2-yl)-1,3,5-triazine (1/1)
aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com
The sulfathiazole molecule in the title 1:1 9H9N3O2S2·C18H12N6, adopts an approximate L-shape [dihedral angle between the five- and six-membered rings = 86.20 (9)°] and features an intramolecular hypervalent S⋯O interaction [2.8666 (15) Å]. Overall, the triazine molecule has the shape of a disk as the pendant pyridine rings are relatively close to coplanar with the central ring [dihedral angles = 18.35 (9), 6.12 (9) and 4.67 (9)°]. In the crystal packing, a linear supramolecular chain aligned along [01-1] is formed as a result of amino–pyridyl N—H⋯N hydrogen bonding with syn-disposed pyridyl molecules of one triazine, and amine–pyridyl N—H⋯N hydrogen bonding with the third pydridyl ring of a second triazine molecule. A three-dimensional architecture arises as the chains are connected by C—H⋯O interactions.
CCCDC reference: 989538
Related literature
For previous co-crystallization studies with sulfathiazole, see: Arman et al. (2012). For the polymorphic 1:1 co-crystals of sulfathiazole and pyridine, see: Drebushchak et al. (2006a,b). For hypervalent S⋯O interactions, see: O'Leary & Wallis (2007).
Experimental
Crystal data
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Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 989538
10.1107/S1600536814004838/hg5388sup1.cif
contains datablocks general, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814004838/hg5388Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814004838/hg5388Isup3.cml
In continuation of co-crystallisation experiments involving sulfathiazole (Arman et al., 2012), herein, the crystal and molecular structure of the title
(I), is described. Except for the description of polymorphic forms of the 1:1 co-crystals formed between sulfathiazole and pyridine (Drebushchak et al., 2006a; Drebushchak et al., 2006b), no other reports of co-crystals of sulfathiazole with pyridyl-containing molecules are known.The components of
(I) are shown in Fig. 1. In the sulfathiazole molecule, there is a twist about the S—N bond as seen in the value of the C4—S2—N2—C1 torsion angle of -77.54 (15)°. The dihedral angle between the five- and six-membered rings is 86.20 (9)°, so that the molecule has an overall L-shape. The observed conformation allows for the formation of an intramolecular hypervalent S···O interaction (O'Leary & Wallis, 2007), i.e. 2.8666 (15) Å. In the triazine molecule, the N7-, N8- and N9-containing pyridyl rings form dihedral angles of 18.35 (9), 6.12 (9) and 4.67 (9)°, respectively, with the central ring, indicating that overall the molecule has a disk shape. In terms of crystal packing (see below), crucially, the N7 and N8 atoms are directed toward each other, which facilitates the formation of amino-N—H···N(pyridyl) hydrogen bonding.Table 1 summarises key hydrogen bonding contacts and Fig. 2 shows the association between the components of the
via amine-N—H with the N9-pydridyl ring of one triazine molecule, and between the amino-N—H atoms and the syn-disposed N7- and N8-pyridyl rings of another molecule, with the result that a linear supramolecular chain is formed along [0 1 -1]. Chains are connected into a three-dimensional architecture by C—H···O interactions, Fig. 3 and Table 1.Sulfathiazole (Sigma-Aldrich) and 2,4,6-tris(pyridin-2-yl)-1,3,5-triazine (Sigma-Aldrich) were used as delivered. Single crystals of (I) used in the present study were harvested from a 1:1 acetone/ethanol (10 ml) solution of a 1:3 ratio of 2,4,6-tris(pyridin-2-yl)-1,3,5-triazine (19 mg) and sulfathiazole (46 mg) by slow evaporation of the solvent. M.pt: 471–475 K.
C-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the
in the riding model approximation with Uiso(H) set to 1.2Ueq(C). The N—H H-atoms were located in a difference Fourier map and refined without restraint for amine-H1n but with Uiso(H) = 1.2Ueq(N) in the cases of amino-H2n and H3n.Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell
CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Molecular structures of (a) 4-amino-N-(1,3-thiazol-2(3H)-ylidene)benzenesulfonamide (sulfathiazole), and (b) 2,4,6-tris(pyridin-2-yl)-1,3,5-triazine, showing atom-labelling scheme and displacement ellipsoids at the 50% probability level. | |
Fig. 2. Supramolecular chains aligned along the [0 1 - 1] direction in (I) sustained by N—H···N hydrogen bonds which are shown as blue dashed lines. | |
Fig. 3. Unit-cell contents in (I) viewed in projection down the a axis. The N—H···N hydrogen bonds and C—H···O interactions are shown as blue and orange dashed lines, respectively. |
C18H12N6·C9H9N3O2S2 | Z = 2 |
Mr = 567.65 | F(000) = 588 |
Triclinic, P1 | Dx = 1.459 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8109 (13) Å | Cell parameters from 4931 reflections |
b = 12.7222 (16) Å | θ = 3.0–40.2° |
c = 13.1696 (14) Å | µ = 0.25 mm−1 |
α = 66.227 (6)° | T = 98 K |
β = 73.797 (6)° | Platelet, gold |
γ = 88.068 (9)° | 0.49 × 0.45 × 0.05 mm |
V = 1292.1 (3) Å3 |
Rigaku AFC12K/SATURN724 diffractometer | 5885 independent reflections |
Radiation source: sealed tube | 5490 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 27.5°, θmin = 2.4° |
ω scans | h = −11→7 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −16→12 |
Tmin = 0.723, Tmax = 1.000 | l = −17→17 |
8512 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.005P)2 + 1.820P] where P = (Fo2 + 2Fc2)/3 |
5885 reflections | (Δ/σ)max < 0.001 |
371 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C18H12N6·C9H9N3O2S2 | γ = 88.068 (9)° |
Mr = 567.65 | V = 1292.1 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.8109 (13) Å | Mo Kα radiation |
b = 12.7222 (16) Å | µ = 0.25 mm−1 |
c = 13.1696 (14) Å | T = 98 K |
α = 66.227 (6)° | 0.49 × 0.45 × 0.05 mm |
β = 73.797 (6)° |
Rigaku AFC12K/SATURN724 diffractometer | 5885 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 5490 reflections with I > 2σ(I) |
Tmin = 0.723, Tmax = 1.000 | Rint = 0.022 |
8512 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.48 e Å−3 |
5885 reflections | Δρmin = −0.39 e Å−3 |
371 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
S1 | −0.04089 (5) | 0.03018 (4) | 0.25889 (5) | 0.02706 (12) | |
S2 | 0.34188 (5) | 0.07956 (3) | 0.19769 (3) | 0.01620 (10) | |
O1 | 0.23839 (15) | 0.12511 (11) | 0.27391 (10) | 0.0209 (3) | |
O2 | 0.49844 (15) | 0.05721 (11) | 0.21024 (11) | 0.0223 (3) | |
N1 | 0.04768 (19) | −0.14266 (13) | 0.21606 (14) | 0.0216 (3) | |
H1N | 0.105 (3) | −0.195 (2) | 0.196 (2) | 0.042 (7)* | |
N2 | 0.26444 (17) | −0.04058 (12) | 0.21139 (12) | 0.0171 (3) | |
N3 | 0.3779 (2) | 0.37727 (13) | −0.28932 (13) | 0.0206 (3) | |
H2N | 0.311 (3) | 0.4266 (19) | −0.3067 (18) | 0.025* | |
H3N | 0.424 (3) | 0.3527 (18) | −0.3439 (19) | 0.025* | |
C1 | 0.1113 (2) | −0.05352 (14) | 0.22511 (14) | 0.0174 (3) | |
C2 | −0.1811 (2) | −0.06008 (18) | 0.2549 (2) | 0.0373 (5) | |
H2 | −0.2907 | −0.0488 | 0.2670 | 0.045* | |
C3 | −0.1146 (2) | −0.14667 (18) | 0.2330 (2) | 0.0322 (5) | |
H3 | −0.1729 | −0.2058 | 0.2292 | 0.039* | |
C4 | 0.3594 (2) | 0.17515 (14) | 0.05455 (14) | 0.0166 (3) | |
C5 | 0.2596 (2) | 0.26325 (15) | 0.02888 (15) | 0.0197 (3) | |
H5 | 0.1867 | 0.2768 | 0.0898 | 0.024* | |
C6 | 0.2662 (2) | 0.33105 (15) | −0.08495 (15) | 0.0203 (3) | |
H6 | 0.1987 | 0.3917 | −0.1014 | 0.024* | |
C7 | 0.3712 (2) | 0.31199 (14) | −0.17696 (14) | 0.0168 (3) | |
C8 | 0.4718 (2) | 0.22258 (15) | −0.14895 (15) | 0.0188 (3) | |
H8 | 0.5445 | 0.2081 | −0.2093 | 0.023* | |
C9 | 0.4662 (2) | 0.15621 (14) | −0.03585 (15) | 0.0182 (3) | |
H9 | 0.5355 | 0.0968 | −0.0189 | 0.022* | |
N4 | 0.71021 (17) | 0.54364 (12) | 0.51665 (12) | 0.0169 (3) | |
N5 | 0.80820 (17) | 0.39937 (12) | 0.65988 (12) | 0.0178 (3) | |
N6 | 0.65974 (18) | 0.54222 (12) | 0.70455 (12) | 0.0180 (3) | |
N7 | 0.50169 (17) | 0.71447 (12) | 0.47243 (12) | 0.0178 (3) | |
N8 | 0.83810 (18) | 0.44100 (13) | 0.36693 (13) | 0.0202 (3) | |
N9 | 0.82618 (18) | 0.29923 (13) | 0.88291 (13) | 0.0209 (3) | |
C10 | 0.6468 (2) | 0.58500 (14) | 0.59665 (14) | 0.0169 (3) | |
C11 | 0.7905 (2) | 0.45104 (14) | 0.55329 (14) | 0.0171 (3) | |
C12 | 0.7410 (2) | 0.44915 (14) | 0.73159 (14) | 0.0173 (3) | |
C13 | 0.5545 (2) | 0.68775 (14) | 0.56574 (14) | 0.0164 (3) | |
C14 | 0.4165 (2) | 0.80561 (15) | 0.44615 (15) | 0.0195 (3) | |
H14 | 0.3777 | 0.8251 | 0.3809 | 0.023* | |
C15 | 0.3814 (2) | 0.87340 (15) | 0.50870 (15) | 0.0211 (4) | |
H15 | 0.3192 | 0.9367 | 0.4873 | 0.025* | |
C16 | 0.4393 (2) | 0.84643 (15) | 0.60282 (16) | 0.0225 (4) | |
H16 | 0.4197 | 0.8921 | 0.6464 | 0.027* | |
C17 | 0.5265 (2) | 0.75155 (15) | 0.63252 (15) | 0.0200 (3) | |
H17 | 0.5665 | 0.7305 | 0.6974 | 0.024* | |
C18 | 0.8671 (2) | 0.39881 (14) | 0.47031 (15) | 0.0175 (3) | |
C19 | 0.9006 (2) | 0.39032 (16) | 0.29539 (16) | 0.0236 (4) | |
H19 | 0.8803 | 0.4190 | 0.2222 | 0.028* | |
C20 | 0.9932 (2) | 0.29850 (16) | 0.32140 (16) | 0.0242 (4) | |
H20 | 1.0335 | 0.2646 | 0.2679 | 0.029* | |
C21 | 1.0255 (2) | 0.25734 (16) | 0.42662 (16) | 0.0236 (4) | |
H21 | 1.0901 | 0.1952 | 0.4467 | 0.028* | |
C22 | 0.9619 (2) | 0.30844 (15) | 0.50265 (15) | 0.0205 (3) | |
H22 | 0.9828 | 0.2822 | 0.5755 | 0.025* | |
C23 | 0.7547 (2) | 0.39769 (14) | 0.85213 (15) | 0.0185 (3) | |
C24 | 0.8363 (2) | 0.25076 (16) | 0.99140 (16) | 0.0253 (4) | |
H24 | 0.8869 | 0.1813 | 1.0139 | 0.030* | |
C25 | 0.7773 (2) | 0.29598 (17) | 1.07283 (16) | 0.0262 (4) | |
H25 | 0.7867 | 0.2582 | 1.1492 | 0.031* | |
C26 | 0.7044 (2) | 0.39730 (17) | 1.04045 (16) | 0.0274 (4) | |
H26 | 0.6625 | 0.4306 | 1.0942 | 0.033* | |
C27 | 0.6937 (2) | 0.44959 (16) | 0.92786 (16) | 0.0238 (4) | |
H27 | 0.6453 | 0.5198 | 0.9031 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0168 (2) | 0.0232 (2) | 0.0442 (3) | 0.00686 (17) | −0.0085 (2) | −0.0174 (2) |
S2 | 0.0161 (2) | 0.0180 (2) | 0.01595 (19) | 0.00379 (15) | −0.00736 (15) | −0.00686 (15) |
O1 | 0.0245 (7) | 0.0229 (6) | 0.0183 (6) | 0.0043 (5) | −0.0080 (5) | −0.0105 (5) |
O2 | 0.0174 (6) | 0.0265 (7) | 0.0237 (6) | 0.0041 (5) | −0.0113 (5) | −0.0078 (5) |
N1 | 0.0203 (8) | 0.0193 (7) | 0.0298 (8) | 0.0049 (6) | −0.0112 (6) | −0.0123 (6) |
N2 | 0.0167 (7) | 0.0161 (7) | 0.0189 (7) | 0.0044 (5) | −0.0068 (6) | −0.0067 (6) |
N3 | 0.0255 (8) | 0.0205 (7) | 0.0166 (7) | 0.0049 (6) | −0.0076 (6) | −0.0076 (6) |
C1 | 0.0180 (8) | 0.0169 (8) | 0.0175 (8) | 0.0059 (6) | −0.0072 (6) | −0.0062 (6) |
C2 | 0.0188 (10) | 0.0312 (11) | 0.0659 (16) | 0.0044 (8) | −0.0167 (10) | −0.0212 (11) |
C3 | 0.0242 (10) | 0.0269 (10) | 0.0508 (13) | 0.0019 (8) | −0.0187 (9) | −0.0162 (9) |
C4 | 0.0176 (8) | 0.0171 (8) | 0.0147 (7) | 0.0005 (6) | −0.0055 (6) | −0.0055 (6) |
C5 | 0.0220 (9) | 0.0200 (8) | 0.0174 (8) | 0.0059 (7) | −0.0049 (7) | −0.0090 (7) |
C6 | 0.0226 (9) | 0.0180 (8) | 0.0207 (8) | 0.0069 (7) | −0.0074 (7) | −0.0078 (7) |
C7 | 0.0183 (8) | 0.0160 (8) | 0.0175 (8) | −0.0017 (6) | −0.0071 (6) | −0.0066 (6) |
C8 | 0.0177 (8) | 0.0212 (8) | 0.0184 (8) | 0.0035 (6) | −0.0046 (7) | −0.0095 (7) |
C9 | 0.0159 (8) | 0.0179 (8) | 0.0215 (8) | 0.0044 (6) | −0.0065 (7) | −0.0081 (7) |
N4 | 0.0177 (7) | 0.0169 (7) | 0.0168 (7) | 0.0015 (5) | −0.0063 (6) | −0.0068 (5) |
N5 | 0.0177 (7) | 0.0179 (7) | 0.0187 (7) | 0.0018 (5) | −0.0068 (6) | −0.0076 (6) |
N6 | 0.0214 (7) | 0.0164 (7) | 0.0174 (7) | 0.0022 (6) | −0.0080 (6) | −0.0067 (6) |
N7 | 0.0191 (7) | 0.0172 (7) | 0.0163 (7) | 0.0018 (5) | −0.0060 (6) | −0.0054 (6) |
N8 | 0.0216 (8) | 0.0211 (7) | 0.0193 (7) | 0.0038 (6) | −0.0065 (6) | −0.0096 (6) |
N9 | 0.0245 (8) | 0.0197 (7) | 0.0210 (7) | 0.0046 (6) | −0.0115 (6) | −0.0079 (6) |
C10 | 0.0170 (8) | 0.0166 (8) | 0.0173 (8) | −0.0002 (6) | −0.0062 (6) | −0.0062 (6) |
C11 | 0.0162 (8) | 0.0165 (8) | 0.0180 (8) | −0.0007 (6) | −0.0046 (6) | −0.0067 (6) |
C12 | 0.0181 (8) | 0.0161 (8) | 0.0185 (8) | −0.0001 (6) | −0.0073 (7) | −0.0065 (6) |
C13 | 0.0163 (8) | 0.0155 (8) | 0.0159 (7) | 0.0005 (6) | −0.0044 (6) | −0.0048 (6) |
C14 | 0.0192 (8) | 0.0198 (8) | 0.0179 (8) | 0.0018 (6) | −0.0071 (7) | −0.0051 (7) |
C15 | 0.0204 (9) | 0.0181 (8) | 0.0225 (8) | 0.0047 (7) | −0.0059 (7) | −0.0064 (7) |
C16 | 0.0271 (9) | 0.0187 (8) | 0.0229 (9) | 0.0040 (7) | −0.0060 (7) | −0.0108 (7) |
C17 | 0.0236 (9) | 0.0192 (8) | 0.0185 (8) | 0.0017 (7) | −0.0076 (7) | −0.0080 (7) |
C18 | 0.0163 (8) | 0.0170 (8) | 0.0183 (8) | −0.0009 (6) | −0.0039 (6) | −0.0068 (6) |
C19 | 0.0278 (10) | 0.0259 (9) | 0.0193 (8) | 0.0041 (7) | −0.0075 (7) | −0.0111 (7) |
C20 | 0.0241 (9) | 0.0252 (9) | 0.0238 (9) | 0.0038 (7) | −0.0028 (7) | −0.0133 (7) |
C21 | 0.0192 (9) | 0.0227 (9) | 0.0281 (9) | 0.0063 (7) | −0.0052 (7) | −0.0109 (7) |
C22 | 0.0183 (8) | 0.0219 (8) | 0.0205 (8) | 0.0026 (7) | −0.0057 (7) | −0.0079 (7) |
C23 | 0.0197 (8) | 0.0176 (8) | 0.0192 (8) | 0.0011 (6) | −0.0082 (7) | −0.0067 (7) |
C24 | 0.0308 (10) | 0.0219 (9) | 0.0252 (9) | 0.0067 (7) | −0.0154 (8) | −0.0071 (7) |
C25 | 0.0322 (10) | 0.0284 (10) | 0.0195 (9) | 0.0049 (8) | −0.0141 (8) | −0.0073 (7) |
C26 | 0.0342 (11) | 0.0299 (10) | 0.0225 (9) | 0.0077 (8) | −0.0115 (8) | −0.0134 (8) |
C27 | 0.0290 (10) | 0.0229 (9) | 0.0224 (9) | 0.0080 (7) | −0.0113 (8) | −0.0098 (7) |
S1—C2 | 1.739 (2) | N7—C13 | 1.347 (2) |
S1—C1 | 1.7559 (17) | N8—C19 | 1.335 (2) |
S2—O2 | 1.4401 (13) | N8—C18 | 1.343 (2) |
S2—O1 | 1.4482 (13) | N9—C24 | 1.337 (2) |
S2—N2 | 1.6167 (15) | N9—C23 | 1.345 (2) |
S2—C4 | 1.7489 (17) | C10—C13 | 1.490 (2) |
N1—C1 | 1.343 (2) | C11—C18 | 1.495 (2) |
N1—C3 | 1.384 (2) | C12—C23 | 1.492 (2) |
N1—H1N | 0.90 (3) | C13—C17 | 1.391 (2) |
N2—C1 | 1.317 (2) | C14—C15 | 1.390 (2) |
N3—C7 | 1.359 (2) | C14—H14 | 0.9500 |
N3—H2N | 0.86 (2) | C15—C16 | 1.383 (3) |
N3—H3N | 0.89 (2) | C15—H15 | 0.9500 |
C2—C3 | 1.326 (3) | C16—C17 | 1.388 (2) |
C2—H2 | 0.9500 | C16—H16 | 0.9500 |
C3—H3 | 0.9500 | C17—H17 | 0.9500 |
C4—C5 | 1.392 (2) | C18—C22 | 1.393 (2) |
C4—C9 | 1.397 (2) | C19—C20 | 1.385 (3) |
C5—C6 | 1.381 (2) | C19—H19 | 0.9500 |
C5—H5 | 0.9500 | C20—C21 | 1.379 (3) |
C6—C7 | 1.407 (2) | C20—H20 | 0.9500 |
C6—H6 | 0.9500 | C21—C22 | 1.388 (2) |
C7—C8 | 1.411 (2) | C21—H21 | 0.9500 |
C8—C9 | 1.372 (2) | C22—H22 | 0.9500 |
C8—H8 | 0.9500 | C23—C27 | 1.388 (2) |
C9—H9 | 0.9500 | C24—C25 | 1.385 (3) |
N4—C11 | 1.341 (2) | C24—H24 | 0.9500 |
N4—C10 | 1.341 (2) | C25—C26 | 1.382 (3) |
N5—C12 | 1.337 (2) | C25—H25 | 0.9500 |
N5—C11 | 1.341 (2) | C26—C27 | 1.389 (3) |
N6—C12 | 1.337 (2) | C26—H26 | 0.9500 |
N6—C10 | 1.338 (2) | C27—H27 | 0.9500 |
N7—C14 | 1.338 (2) | ||
C2—S1—C1 | 91.05 (9) | N4—C11—C18 | 118.45 (15) |
O2—S2—O1 | 117.20 (8) | N5—C11—C18 | 116.06 (15) |
O2—S2—N2 | 105.59 (8) | N6—C12—N5 | 125.13 (15) |
O1—S2—N2 | 111.61 (8) | N6—C12—C23 | 116.30 (15) |
O2—S2—C4 | 108.79 (8) | N5—C12—C23 | 118.56 (15) |
O1—S2—C4 | 108.12 (8) | N7—C13—C17 | 122.90 (16) |
N2—S2—C4 | 104.82 (8) | N7—C13—C10 | 117.34 (15) |
C1—N1—C3 | 115.58 (16) | C17—C13—C10 | 119.76 (15) |
C1—N1—H1N | 123.4 (16) | N7—C14—C15 | 123.83 (16) |
C3—N1—H1N | 120.9 (16) | N7—C14—H14 | 118.1 |
C1—N2—S2 | 119.62 (12) | C15—C14—H14 | 118.1 |
C7—N3—H2N | 121.0 (14) | C16—C15—C14 | 118.37 (16) |
C7—N3—H3N | 120.2 (14) | C16—C15—H15 | 120.8 |
H2N—N3—H3N | 115 (2) | C14—C15—H15 | 120.8 |
N2—C1—N1 | 121.27 (15) | C15—C16—C17 | 118.85 (16) |
N2—C1—S1 | 129.99 (13) | C15—C16—H16 | 120.6 |
N1—C1—S1 | 108.72 (13) | C17—C16—H16 | 120.6 |
C3—C2—S1 | 111.04 (16) | C16—C17—C13 | 118.88 (16) |
C3—C2—H2 | 124.5 | C16—C17—H17 | 120.6 |
S1—C2—H2 | 124.5 | C13—C17—H17 | 120.6 |
C2—C3—N1 | 113.58 (18) | N8—C18—C22 | 122.68 (16) |
C2—C3—H3 | 123.2 | N8—C18—C11 | 117.51 (15) |
N1—C3—H3 | 123.2 | C22—C18—C11 | 119.80 (15) |
C5—C4—C9 | 119.38 (15) | N8—C19—C20 | 123.98 (17) |
C5—C4—S2 | 121.31 (13) | N8—C19—H19 | 118.0 |
C9—C4—S2 | 119.07 (13) | C20—C19—H19 | 118.0 |
C6—C5—C4 | 120.18 (16) | C21—C20—C19 | 118.51 (17) |
C6—C5—H5 | 119.9 | C21—C20—H20 | 120.7 |
C4—C5—H5 | 119.9 | C19—C20—H20 | 120.7 |
C5—C6—C7 | 121.20 (16) | C20—C21—C22 | 118.67 (17) |
C5—C6—H6 | 119.4 | C20—C21—H21 | 120.7 |
C7—C6—H6 | 119.4 | C22—C21—H21 | 120.7 |
N3—C7—C6 | 121.83 (16) | C21—C22—C18 | 118.91 (17) |
N3—C7—C8 | 120.52 (16) | C21—C22—H22 | 120.5 |
C6—C7—C8 | 117.64 (15) | C18—C22—H22 | 120.5 |
C9—C8—C7 | 121.02 (16) | N9—C23—C27 | 122.59 (16) |
C9—C8—H8 | 119.5 | N9—C23—C12 | 116.79 (15) |
C7—C8—H8 | 119.5 | C27—C23—C12 | 120.61 (16) |
C8—C9—C4 | 120.57 (16) | N9—C24—C25 | 123.73 (17) |
C8—C9—H9 | 119.7 | N9—C24—H24 | 118.1 |
C4—C9—H9 | 119.7 | C25—C24—H24 | 118.1 |
C11—N4—C10 | 114.23 (14) | C26—C25—C24 | 118.44 (17) |
C12—N5—C11 | 114.75 (15) | C26—C25—H25 | 120.8 |
C12—N6—C10 | 114.91 (15) | C24—C25—H25 | 120.8 |
C14—N7—C13 | 117.16 (15) | C25—C26—C27 | 118.78 (18) |
C19—N8—C18 | 117.21 (16) | C25—C26—H26 | 120.6 |
C24—N9—C23 | 117.49 (16) | C27—C26—H26 | 120.6 |
N6—C10—N4 | 125.46 (16) | C23—C27—C26 | 118.97 (17) |
N6—C10—C13 | 115.56 (15) | C23—C27—H27 | 120.5 |
N4—C10—C13 | 118.97 (15) | C26—C27—H27 | 120.5 |
N4—C11—N5 | 125.49 (15) | ||
O2—S2—N2—C1 | 167.64 (13) | C11—N5—C12—N6 | 0.7 (2) |
O1—S2—N2—C1 | 39.26 (16) | C11—N5—C12—C23 | −179.92 (15) |
C4—S2—N2—C1 | −77.54 (15) | C14—N7—C13—C17 | −1.2 (2) |
S2—N2—C1—N1 | 167.95 (13) | C14—N7—C13—C10 | 178.86 (15) |
S2—N2—C1—S1 | −13.5 (2) | N6—C10—C13—N7 | −162.39 (15) |
C3—N1—C1—N2 | 179.67 (17) | N4—C10—C13—N7 | 18.1 (2) |
C3—N1—C1—S1 | 0.9 (2) | N6—C10—C13—C17 | 17.7 (2) |
C2—S1—C1—N2 | 179.95 (18) | N4—C10—C13—C17 | −161.75 (16) |
C2—S1—C1—N1 | −1.38 (15) | C13—N7—C14—C15 | 0.5 (3) |
C1—S1—C2—C3 | 1.62 (19) | N7—C14—C15—C16 | 0.9 (3) |
S1—C2—C3—N1 | −1.4 (3) | C14—C15—C16—C17 | −1.5 (3) |
C1—N1—C3—C2 | 0.4 (3) | C15—C16—C17—C13 | 0.8 (3) |
O2—S2—C4—C5 | −140.37 (14) | N7—C13—C17—C16 | 0.6 (3) |
O1—S2—C4—C5 | −12.10 (17) | C10—C13—C17—C16 | −179.51 (16) |
N2—S2—C4—C5 | 107.07 (15) | C19—N8—C18—C22 | 2.0 (3) |
O2—S2—C4—C9 | 45.36 (16) | C19—N8—C18—C11 | −176.87 (16) |
O1—S2—C4—C9 | 173.63 (13) | N4—C11—C18—N8 | −6.3 (2) |
N2—S2—C4—C9 | −67.20 (15) | N5—C11—C18—N8 | 173.32 (15) |
C9—C4—C5—C6 | 0.1 (3) | N4—C11—C18—C22 | 174.83 (16) |
S2—C4—C5—C6 | −174.18 (14) | N5—C11—C18—C22 | −5.6 (2) |
C4—C5—C6—C7 | 1.0 (3) | C18—N8—C19—C20 | −0.5 (3) |
C5—C6—C7—N3 | 179.31 (17) | N8—C19—C20—C21 | −1.0 (3) |
C5—C6—C7—C8 | −1.2 (3) | C19—C20—C21—C22 | 1.0 (3) |
N3—C7—C8—C9 | 179.96 (16) | C20—C21—C22—C18 | 0.4 (3) |
C6—C7—C8—C9 | 0.5 (3) | N8—C18—C22—C21 | −2.0 (3) |
C7—C8—C9—C4 | 0.5 (3) | C11—C18—C22—C21 | 176.84 (16) |
C5—C4—C9—C8 | −0.8 (3) | C24—N9—C23—C27 | 0.5 (3) |
S2—C4—C9—C8 | 173.57 (14) | C24—N9—C23—C12 | −178.59 (16) |
C12—N6—C10—N4 | −1.4 (2) | N6—C12—C23—N9 | 175.31 (15) |
C12—N6—C10—C13 | 179.14 (14) | N5—C12—C23—N9 | −4.1 (2) |
C11—N4—C10—N6 | 0.7 (2) | N6—C12—C23—C27 | −3.8 (2) |
C11—N4—C10—C13 | −179.88 (14) | N5—C12—C23—C27 | 176.81 (17) |
C10—N4—C11—N5 | 0.9 (2) | C23—N9—C24—C25 | 0.2 (3) |
C10—N4—C11—C18 | −179.52 (15) | N9—C24—C25—C26 | −0.4 (3) |
C12—N5—C11—N4 | −1.6 (2) | C24—C25—C26—C27 | −0.1 (3) |
C12—N5—C11—C18 | 178.84 (14) | N9—C23—C27—C26 | −1.0 (3) |
C10—N6—C12—N5 | 0.7 (2) | C12—C23—C27—C26 | 178.08 (17) |
C10—N6—C12—C23 | −178.71 (15) | C25—C26—C27—C23 | 0.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N9i | 0.90 (3) | 1.98 (3) | 2.835 (3) | 158 (2) |
N3—H2N···N8ii | 0.85 (3) | 2.13 (3) | 2.983 (3) | 174 (2) |
N3—H3N···N7ii | 0.89 (2) | 2.13 (2) | 3.010 (2) | 171 (3) |
C2—H2···O2iii | 0.95 | 2.37 | 3.237 (3) | 151 |
C16—H16···O2iv | 0.95 | 2.50 | 3.331 (2) | 145 |
C20—H20···O1v | 0.95 | 2.48 | 3.156 (3) | 128 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+1; (v) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N9i | 0.90 (3) | 1.98 (3) | 2.835 (3) | 158 (2) |
N3—H2N···N8ii | 0.85 (3) | 2.13 (3) | 2.983 (3) | 174 (2) |
N3—H3N···N7ii | 0.89 (2) | 2.13 (2) | 3.010 (2) | 171 (3) |
C2—H2···O2iii | 0.95 | 2.37 | 3.237 (3) | 151 |
C16—H16···O2iv | 0.95 | 2.50 | 3.331 (2) | 145 |
C20—H20···O1v | 0.95 | 2.48 | 3.156 (3) | 128 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+1; (v) x+1, y, z. |
Acknowledgements
We gratefully thank the Ministry of Higher Education (Malaysia) and the University of Malaya for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).
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