organic compounds
H-thiazolo[3,2-a]pyrimidin-8-ium chloride
of 2-acetyl-5-(3,4-dimethoxyphenyl)-6-ethoxycarbonyl-3,7-dimethyl-5aDepartment of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore 560 001, Karnataka, India
*Correspondence e-mail: noorsb@rediffmail.com
The title molecular salt, C21H25N2O5S+·Cl−, crystallizes with two ion pairs in the The cations have similar conformations (r.m.s. overlay fit = 0.40 Å), with one of them showing disorder of the terminal methyl group of the ester in a 0.72 (2):0.28 (2) ratio. In the first cation, the 3,4-dimethoxy-substituted phenyl ring subtends a dihedral angle of 88.38 (7)° with the pyrimidine ring and 6.79 (8)° with the thiazole ring. The equivalent data for the second cation are 89.97 (3) and 6.42 (7)°, respectively. The pyrimidine ring adopts a sofa conformation in each cation. In the crystal, the components are linked by N—H⋯Cl hydrogen bonds, generating isolated ion pairs. The ion pairs are are linked by C—H⋯O interactions, generating a three-dimensional network. In addition, a weak C—H⋯π interaction is observed.
Keywords: crystal structure; salt; pyrimidinium; chloride; pyrimidine derivatives; pharmacological properties; biological activity; hydrogen bonding; C—H⋯π interactions.
CCDC reference: 1421372
1. Related literature
For the pharmacological properties of pyrimidine derivatives, see: Ashok et al. (2007); Alam et al. (2010); Kulakov et al. (2009); Zhi et al. (2008). For conformational effects on biological activity, see: Rovnyak et al. (1995). For related structures, see: Prasad et al. (2014); Nagarajaiah et al. (2012).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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 CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 1421372
10.1107/S2056989015016229/hb7484sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016229/hb7484Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016229/hb7484Isup3.cml
A mixture of 4-(3,4-dimethoxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro- pyrimidine-5-carboxylic acid ethyl ester (10 mmol) and 3-chloro-2,4- pentanedione (10 mmol) was refluxed in dry ethanol (20 mmol) for 12 h. The excess of solvent was distilled off and the solid hydrochloride salt that separated was collected by filtration, suspended in water and neutralized by aqueous sodium carbonate solution to yield the free base. The solution was filtered, the solid washed with water, dried and recrystallized from ethyl acetate to give the title compound (74% yield, mp 385 K). The compound was recrystallized by slow evaporation from 1:1 mixture of ethyl acetate and methanol, yielding pale yellow blocks.
The H atoms were placed at calculated positions in the riding-model approximation with C—H = 0.95° A, 1.00 ° A and 0.96 ° A for aromatic, methyne and methyl H-atoms respectively, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and Uiso(H) = 1.2Ueq(C) for other hydrogen atoms.
Data collection: SMART (Bruker, 1998); cell
SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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 CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. Unit-cell packing of the title compound showing C—H···O and N—H···Cl interactions with dotted lines. H-atoms not involved in hydrogen bonding have been excluded. | |
Fig. 3. Unit-cell packing depicting the intermolecular C—H···π interactions with dotted lines. |
C21H25N2O5S+·Cl− | Z = 4 |
Mr = 452.94 | F(000) = 952 |
Triclinic, P1 | Dx = 1.373 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9000 (6) Å | Cell parameters from 7693 reflections |
b = 11.8563 (7) Å | θ = 2.1–25.0° |
c = 19.0377 (11) Å | µ = 0.31 mm−1 |
α = 80.827 (2)° | T = 100 K |
β = 83.999 (2)° | Block, colorless |
γ = 86.071 (2)° | 0.40 × 0.35 × 0.30 mm |
V = 2190.9 (2) Å3 |
Bruker SMART APEX CCD diffractometer | 7693 independent reflections |
Radiation source: fine-focus sealed tube | 4545 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −11→11 |
Tmin = 0.947, Tmax = 0.953 | k = −14→14 |
26782 measured reflections | l = −22→22 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0651P)2] where P = (Fo2 + 2Fc2)/3 |
7693 reflections | (Δ/σ)max = 0.001 |
565 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C21H25N2O5S+·Cl− | γ = 86.071 (2)° |
Mr = 452.94 | V = 2190.9 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.9000 (6) Å | Mo Kα radiation |
b = 11.8563 (7) Å | µ = 0.31 mm−1 |
c = 19.0377 (11) Å | T = 100 K |
α = 80.827 (2)° | 0.40 × 0.35 × 0.30 mm |
β = 83.999 (2)° |
Bruker SMART APEX CCD diffractometer | 7693 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 4545 reflections with I > 2σ(I) |
Tmin = 0.947, Tmax = 0.953 | Rint = 0.077 |
26782 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.46 e Å−3 |
7693 reflections | Δρmin = −0.39 e Å−3 |
565 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 | Occ. (<1) | |
S1A | 0.55372 (9) | 0.82102 (7) | 0.06988 (5) | 0.0231 (2) | |
S1B | 1.58661 (9) | 0.56682 (7) | 0.41046 (5) | 0.0236 (2) | |
Cl1A | 0.26054 (8) | 0.98395 (7) | 0.07281 (4) | 0.0258 (2) | |
O3B | 1.1844 (2) | 0.61890 (18) | 0.07522 (11) | 0.0219 (6) | |
O3A | 0.9580 (2) | 0.78589 (18) | 0.40798 (11) | 0.0233 (6) | |
N1A | 0.5318 (3) | 1.0231 (2) | 0.11824 (14) | 0.0216 (7) | |
H1A | 0.4428 | 1.0205 | 0.1199 | 0.026* | |
N2A | 0.7460 (3) | 0.9302 (2) | 0.10151 (13) | 0.0183 (7) | |
O4A | 1.1459 (2) | 0.82817 (19) | 0.30585 (12) | 0.0274 (6) | |
O4B | 0.9931 (2) | 0.58909 (18) | 0.17602 (11) | 0.0248 (6) | |
O2A | 0.9189 (2) | 1.20032 (18) | 0.15574 (12) | 0.0255 (6) | |
N2B | 1.3831 (3) | 0.4659 (2) | 0.38338 (13) | 0.0183 (6) | |
C11A | 0.7792 (3) | 0.8628 (3) | 0.33236 (17) | 0.0200 (8) | |
H11A | 0.7091 | 0.8437 | 0.3696 | 0.024* | |
O5A | 0.6313 (2) | 0.61710 (19) | 0.01754 (13) | 0.0312 (6) | |
N1B | 1.5897 (3) | 0.3652 (2) | 0.36194 (14) | 0.0243 (7) | |
H1B | 1.6789 | 0.3658 | 0.3554 | 0.029* | |
C9A | 0.8485 (3) | 0.9473 (3) | 0.21133 (16) | 0.0165 (8) | |
O5B | 1.5264 (2) | 0.7675 (2) | 0.46921 (13) | 0.0330 (6) | |
C14A | 0.9846 (3) | 0.9182 (3) | 0.22318 (17) | 0.0192 (8) | |
H14A | 1.0548 | 0.9376 | 0.1861 | 0.023* | |
O1A | 0.7242 (2) | 1.2983 (2) | 0.18268 (13) | 0.0312 (6) | |
C11B | 1.3560 (3) | 0.5287 (3) | 0.15165 (17) | 0.0211 (8) | |
H11B | 1.4278 | 0.5424 | 0.1146 | 0.025* | |
C13B | 1.1196 (3) | 0.5473 (3) | 0.19403 (17) | 0.0188 (8) | |
C10A | 0.7475 (3) | 0.9186 (3) | 0.26544 (17) | 0.0200 (8) | |
H10A | 0.6550 | 0.9371 | 0.2571 | 0.024* | |
C2B | 1.5186 (3) | 0.4558 (3) | 0.38183 (17) | 0.0220 (8) | |
C17B | 1.3250 (3) | 0.5635 (3) | 0.40926 (16) | 0.0197 (8) | |
C5A | 0.8131 (3) | 1.0096 (3) | 0.13895 (17) | 0.0174 (8) | |
H5A | 0.8993 | 1.0330 | 0.1097 | 0.021* | |
C9B | 1.2801 (3) | 0.4514 (3) | 0.27319 (17) | 0.0181 (8) | |
C19B | 1.4225 (3) | 0.6284 (3) | 0.42452 (17) | 0.0204 (8) | |
C6A | 0.7208 (3) | 1.1153 (3) | 0.14404 (16) | 0.0185 (8) | |
C2A | 0.6109 (3) | 0.9356 (3) | 0.09945 (16) | 0.0185 (8) | |
C21B | 1.2888 (3) | 0.8079 (3) | 0.46114 (18) | 0.0283 (9) | |
H21A | 1.2298 | 0.7711 | 0.5017 | 0.042* | |
H21B | 1.2430 | 0.8144 | 0.4174 | 0.042* | |
H21C | 1.3081 | 0.8844 | 0.4695 | 0.042* | |
C14B | 1.1472 (3) | 0.4909 (3) | 0.26048 (17) | 0.0196 (8) | |
H14B | 1.0757 | 0.4789 | 0.2978 | 0.024* | |
C12A | 0.9138 (3) | 0.8359 (3) | 0.34386 (17) | 0.0197 (8) | |
C13A | 1.0166 (3) | 0.8614 (3) | 0.28869 (17) | 0.0184 (8) | |
C12B | 1.2245 (3) | 0.5658 (3) | 0.13895 (17) | 0.0178 (8) | |
C17A | 0.8121 (3) | 0.8373 (3) | 0.07323 (17) | 0.0197 (8) | |
C20A | 0.7354 (4) | 0.6582 (3) | 0.02851 (17) | 0.0237 (8) | |
C7A | 0.5872 (3) | 1.1187 (3) | 0.13521 (17) | 0.0200 (8) | |
C10B | 1.3838 (3) | 0.4711 (3) | 0.21867 (17) | 0.0220 (8) | |
H10B | 1.4745 | 0.4452 | 0.2270 | 0.026* | |
C5B | 1.3078 (3) | 0.3898 (3) | 0.34687 (17) | 0.0204 (8) | |
H5B | 1.2187 | 0.3740 | 0.3755 | 0.025* | |
C20B | 1.4185 (4) | 0.7379 (3) | 0.45335 (17) | 0.0257 (9) | |
C3A | 0.7829 (3) | 1.2151 (3) | 0.16276 (17) | 0.0202 (8) | |
C6B | 1.3908 (4) | 0.2779 (3) | 0.34601 (17) | 0.0218 (8) | |
C7B | 1.5250 (4) | 0.2687 (3) | 0.35115 (17) | 0.0252 (9) | |
C1A | 0.4850 (3) | 1.2162 (3) | 0.14002 (19) | 0.0277 (9) | |
H1A1 | 0.4466 | 1.2143 | 0.1897 | 0.042* | |
H1A2 | 0.4122 | 1.2100 | 0.1100 | 0.042* | |
H1A3 | 0.5291 | 1.2885 | 0.1235 | 0.042* | |
C19A | 0.7212 (3) | 0.7669 (3) | 0.05676 (17) | 0.0210 (8) | |
C16B | 0.8851 (3) | 0.5858 (3) | 0.23198 (18) | 0.0323 (10) | |
H16A | 0.8678 | 0.5061 | 0.2517 | 0.048* | |
H16B | 0.8027 | 0.6239 | 0.2129 | 0.048* | |
H16C | 0.9106 | 0.6253 | 0.2697 | 0.048* | |
C18A | 0.9630 (3) | 0.8299 (3) | 0.06129 (17) | 0.0222 (8) | |
H18A | 0.9998 | 0.7761 | 0.1001 | 0.033* | |
H18B | 0.9977 | 0.9056 | 0.0603 | 0.033* | |
H18C | 0.9908 | 0.8030 | 0.0156 | 0.033* | |
C15B | 1.2870 (3) | 0.6565 (3) | 0.01999 (18) | 0.0291 (9) | |
H15A | 1.3409 | 0.7123 | 0.0359 | 0.044* | |
H15B | 1.2443 | 0.6921 | −0.0229 | 0.044* | |
H15C | 1.3464 | 0.5908 | 0.0089 | 0.044* | |
C1B | 1.6186 (4) | 0.1652 (3) | 0.34882 (19) | 0.0339 (10) | |
H1B1 | 1.5867 | 0.1038 | 0.3864 | 0.051* | |
H1B2 | 1.7105 | 0.1836 | 0.3565 | 0.051* | |
H1B3 | 1.6202 | 0.1403 | 0.3021 | 0.051* | |
C18B | 1.1749 (3) | 0.5825 (3) | 0.41897 (18) | 0.0243 (9) | |
H18D | 1.1493 | 0.6179 | 0.4620 | 0.036* | |
H18E | 1.1323 | 0.5091 | 0.4242 | 0.036* | |
H18F | 1.1439 | 0.6332 | 0.3772 | 0.036* | |
C15A | 0.8599 (4) | 0.7449 (3) | 0.46416 (18) | 0.0349 (10) | |
H15D | 0.7958 | 0.8080 | 0.4749 | 0.052* | |
H15E | 0.9056 | 0.7135 | 0.5068 | 0.052* | |
H15F | 0.8105 | 0.6849 | 0.4496 | 0.052* | |
O2B | 1.1810 (3) | 0.1986 (2) | 0.35168 (14) | 0.0473 (8) | |
O1B | 1.3641 (3) | 0.0864 (2) | 0.32700 (16) | 0.0561 (9) | |
C16A | 1.2520 (3) | 0.8421 (3) | 0.24971 (19) | 0.0390 (11) | |
H16D | 1.2328 | 0.8007 | 0.2116 | 0.058* | |
H16E | 1.3383 | 0.8118 | 0.2680 | 0.058* | |
H16F | 1.2584 | 0.9236 | 0.2307 | 0.058* | |
C21A | 0.8716 (3) | 0.6000 (3) | 0.01681 (19) | 0.0322 (10) | |
H21D | 0.8623 | 0.5290 | −0.0020 | 0.048* | |
H21E | 0.9125 | 0.5824 | 0.0622 | 0.048* | |
H21F | 0.9298 | 0.6504 | −0.0176 | 0.048* | |
C8A | 0.9939 (3) | 1.2897 (3) | 0.17477 (19) | 0.0288 (9) | |
H8A1 | 0.9670 | 1.3005 | 0.2249 | 0.035* | |
H8A2 | 0.9765 | 1.3631 | 0.1432 | 0.035* | |
C4A | 1.1415 (3) | 1.2505 (3) | 0.16523 (19) | 0.0299 (9) | |
H4A1 | 1.1584 | 1.1814 | 0.1996 | 0.045* | |
H4A2 | 1.1980 | 1.3110 | 0.1734 | 0.045* | |
H4A3 | 1.1642 | 1.2336 | 0.1165 | 0.045* | |
C3B | 1.3152 (4) | 0.1763 (3) | 0.34012 (19) | 0.0322 (10) | |
C8B | 1.0940 (5) | 0.1052 (4) | 0.3517 (3) | 0.0723 (16) | |
H8B1 | 1.0246 | 0.1296 | 0.3178 | 0.087* | |
H8B2 | 1.1491 | 0.0396 | 0.3356 | 0.087* | |
C4B | 1.0291 (12) | 0.0708 (9) | 0.4207 (6) | 0.053 (3) | 0.72 (2) |
H4B1 | 0.9833 | 0.1376 | 0.4390 | 0.080* | 0.72 (2) |
H4B2 | 1.0969 | 0.0359 | 0.4527 | 0.080* | 0.72 (2) |
H4B3 | 0.9619 | 0.0149 | 0.4182 | 0.080* | 0.72 (2) |
C4B' | 0.975 (2) | 0.1130 (18) | 0.3817 (19) | 0.045 (8) | 0.28 (2) |
H4B4 | 0.9286 | 0.0432 | 0.3801 | 0.068* | 0.28 (2) |
H4B5 | 0.9250 | 0.1790 | 0.3567 | 0.068* | 0.28 (2) |
H4B6 | 0.9785 | 0.1231 | 0.4315 | 0.068* | 0.28 (2) |
Cl1B | 0.87338 (9) | 0.39271 (8) | 0.39496 (5) | 0.0349 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0175 (5) | 0.0254 (5) | 0.0285 (5) | −0.0026 (4) | −0.0046 (4) | −0.0088 (4) |
S1B | 0.0202 (5) | 0.0268 (5) | 0.0254 (5) | −0.0032 (4) | −0.0064 (4) | −0.0050 (4) |
Cl1A | 0.0188 (5) | 0.0344 (6) | 0.0240 (5) | −0.0049 (4) | −0.0049 (4) | −0.0001 (4) |
O3B | 0.0190 (13) | 0.0284 (14) | 0.0164 (13) | −0.0025 (11) | 0.0002 (11) | 0.0012 (11) |
O3A | 0.0181 (13) | 0.0334 (15) | 0.0160 (13) | −0.0020 (11) | −0.0025 (11) | 0.0039 (11) |
N1A | 0.0111 (15) | 0.0268 (18) | 0.0286 (17) | 0.0015 (13) | −0.0022 (13) | −0.0096 (14) |
N2A | 0.0165 (16) | 0.0194 (16) | 0.0196 (16) | 0.0015 (13) | −0.0049 (13) | −0.0035 (13) |
O4A | 0.0138 (13) | 0.0422 (16) | 0.0225 (14) | 0.0025 (11) | −0.0031 (12) | 0.0056 (11) |
O4B | 0.0176 (14) | 0.0328 (15) | 0.0211 (13) | 0.0024 (11) | −0.0013 (11) | 0.0027 (11) |
O2A | 0.0155 (13) | 0.0244 (14) | 0.0400 (15) | −0.0045 (10) | −0.0040 (12) | −0.0127 (11) |
N2B | 0.0184 (17) | 0.0186 (17) | 0.0177 (16) | −0.0011 (13) | −0.0037 (13) | −0.0009 (13) |
C11A | 0.020 (2) | 0.024 (2) | 0.0153 (19) | −0.0058 (16) | 0.0018 (16) | −0.0019 (15) |
O5A | 0.0253 (15) | 0.0298 (15) | 0.0424 (16) | −0.0015 (12) | −0.0096 (13) | −0.0130 (12) |
N1B | 0.0200 (17) | 0.0266 (18) | 0.0275 (17) | −0.0002 (14) | −0.0050 (14) | −0.0064 (14) |
C9A | 0.0164 (19) | 0.0173 (19) | 0.0161 (19) | −0.0024 (15) | −0.0009 (16) | −0.0036 (15) |
O5B | 0.0264 (15) | 0.0367 (16) | 0.0397 (16) | −0.0065 (12) | −0.0062 (13) | −0.0135 (13) |
C14A | 0.0156 (19) | 0.022 (2) | 0.020 (2) | −0.0028 (15) | −0.0014 (16) | −0.0027 (16) |
O1A | 0.0237 (14) | 0.0276 (16) | 0.0455 (17) | 0.0033 (12) | −0.0050 (13) | −0.0161 (13) |
C11B | 0.022 (2) | 0.023 (2) | 0.018 (2) | −0.0075 (16) | 0.0024 (16) | −0.0017 (16) |
C13B | 0.018 (2) | 0.018 (2) | 0.021 (2) | −0.0011 (15) | −0.0058 (17) | −0.0037 (15) |
C10A | 0.0190 (19) | 0.021 (2) | 0.022 (2) | 0.0003 (15) | −0.0073 (17) | −0.0043 (16) |
C2B | 0.020 (2) | 0.028 (2) | 0.018 (2) | 0.0010 (17) | −0.0063 (17) | −0.0013 (16) |
C17B | 0.025 (2) | 0.021 (2) | 0.0122 (18) | −0.0003 (16) | −0.0020 (16) | 0.0006 (15) |
C5A | 0.0119 (18) | 0.020 (2) | 0.0215 (19) | −0.0001 (15) | −0.0024 (16) | −0.0062 (15) |
C9B | 0.021 (2) | 0.019 (2) | 0.0145 (19) | −0.0051 (15) | −0.0007 (16) | −0.0014 (15) |
C19B | 0.019 (2) | 0.025 (2) | 0.0164 (19) | −0.0001 (16) | −0.0058 (16) | −0.0009 (16) |
C6A | 0.023 (2) | 0.018 (2) | 0.0150 (18) | −0.0010 (15) | −0.0026 (16) | −0.0019 (15) |
C2A | 0.018 (2) | 0.025 (2) | 0.0139 (19) | −0.0012 (16) | −0.0033 (16) | −0.0035 (15) |
C21B | 0.031 (2) | 0.028 (2) | 0.026 (2) | 0.0024 (18) | −0.0024 (18) | −0.0051 (17) |
C14B | 0.018 (2) | 0.022 (2) | 0.019 (2) | −0.0057 (15) | 0.0015 (16) | −0.0055 (16) |
C12A | 0.024 (2) | 0.019 (2) | 0.017 (2) | −0.0028 (15) | −0.0078 (17) | −0.0004 (15) |
C13A | 0.0152 (19) | 0.019 (2) | 0.020 (2) | 0.0012 (15) | −0.0021 (17) | −0.0009 (15) |
C12B | 0.025 (2) | 0.0124 (19) | 0.017 (2) | −0.0024 (15) | −0.0081 (17) | −0.0011 (15) |
C17A | 0.0191 (19) | 0.020 (2) | 0.0196 (19) | 0.0037 (16) | −0.0041 (16) | −0.0025 (16) |
C20A | 0.026 (2) | 0.026 (2) | 0.020 (2) | −0.0009 (17) | −0.0056 (17) | −0.0050 (16) |
C7A | 0.024 (2) | 0.018 (2) | 0.0186 (19) | −0.0032 (16) | −0.0040 (17) | −0.0020 (15) |
C10B | 0.018 (2) | 0.025 (2) | 0.025 (2) | −0.0026 (16) | −0.0078 (17) | −0.0042 (16) |
C5B | 0.021 (2) | 0.021 (2) | 0.019 (2) | −0.0047 (16) | −0.0042 (16) | −0.0015 (15) |
C20B | 0.033 (2) | 0.029 (2) | 0.014 (2) | −0.0074 (18) | 0.0012 (18) | 0.0004 (16) |
C3A | 0.020 (2) | 0.022 (2) | 0.0182 (19) | 0.0014 (16) | −0.0044 (17) | −0.0012 (16) |
C6B | 0.031 (2) | 0.021 (2) | 0.0134 (19) | −0.0059 (17) | −0.0053 (17) | −0.0001 (15) |
C7B | 0.035 (2) | 0.026 (2) | 0.0145 (19) | 0.0016 (18) | −0.0071 (17) | −0.0030 (16) |
C1A | 0.022 (2) | 0.028 (2) | 0.035 (2) | 0.0023 (17) | −0.0065 (18) | −0.0086 (18) |
C19A | 0.020 (2) | 0.024 (2) | 0.020 (2) | −0.0003 (16) | −0.0057 (16) | −0.0027 (16) |
C16B | 0.021 (2) | 0.047 (3) | 0.028 (2) | 0.0037 (18) | 0.0008 (19) | −0.0043 (19) |
C18A | 0.0162 (19) | 0.026 (2) | 0.025 (2) | 0.0006 (15) | −0.0026 (16) | −0.0060 (16) |
C15B | 0.031 (2) | 0.035 (2) | 0.021 (2) | −0.0071 (18) | −0.0069 (18) | 0.0009 (17) |
C1B | 0.041 (2) | 0.029 (2) | 0.032 (2) | 0.0058 (19) | −0.011 (2) | −0.0054 (18) |
C18B | 0.021 (2) | 0.029 (2) | 0.025 (2) | 0.0015 (16) | −0.0047 (17) | −0.0079 (17) |
C15A | 0.030 (2) | 0.053 (3) | 0.018 (2) | −0.010 (2) | −0.0044 (19) | 0.0081 (18) |
O2B | 0.0406 (18) | 0.0509 (19) | 0.057 (2) | −0.0283 (15) | 0.0087 (15) | −0.0242 (15) |
O1B | 0.062 (2) | 0.0254 (18) | 0.086 (2) | −0.0040 (15) | −0.0212 (18) | −0.0155 (16) |
C16A | 0.016 (2) | 0.062 (3) | 0.031 (2) | 0.0072 (19) | −0.0007 (19) | 0.010 (2) |
C21A | 0.031 (2) | 0.032 (2) | 0.040 (2) | 0.0078 (18) | −0.015 (2) | −0.0190 (19) |
C8A | 0.027 (2) | 0.025 (2) | 0.038 (2) | −0.0073 (17) | −0.0041 (19) | −0.0133 (18) |
C4A | 0.022 (2) | 0.029 (2) | 0.041 (2) | −0.0012 (17) | −0.0060 (19) | −0.0137 (18) |
C3B | 0.048 (3) | 0.028 (3) | 0.021 (2) | −0.010 (2) | −0.009 (2) | 0.0003 (18) |
C8B | 0.071 (4) | 0.080 (4) | 0.078 (4) | −0.057 (3) | 0.011 (3) | −0.040 (3) |
C4B | 0.055 (6) | 0.031 (5) | 0.072 (7) | −0.016 (4) | 0.007 (5) | −0.008 (4) |
C4B' | 0.034 (12) | 0.013 (10) | 0.09 (2) | −0.003 (8) | −0.003 (12) | −0.013 (10) |
Cl1B | 0.0262 (5) | 0.0494 (7) | 0.0274 (5) | −0.0088 (5) | −0.0059 (4) | 0.0044 (5) |
S1A—C2A | 1.702 (3) | C12A—C13A | 1.396 (4) |
S1A—C19A | 1.744 (3) | C17A—C19A | 1.361 (4) |
S1B—C2B | 1.706 (3) | C17A—C18A | 1.485 (4) |
S1B—C19B | 1.747 (3) | C20A—C19A | 1.466 (4) |
O3B—C12B | 1.360 (3) | C20A—C21A | 1.484 (4) |
O3B—C15B | 1.423 (4) | C7A—C1A | 1.491 (4) |
O3A—C12A | 1.371 (4) | C10B—H10B | 0.9500 |
O3A—C15A | 1.416 (4) | C5B—C6B | 1.514 (4) |
N1A—C2A | 1.330 (4) | C5B—H5B | 1.0000 |
N1A—C7A | 1.389 (4) | C6B—C7B | 1.339 (4) |
N1A—H1A | 0.8800 | C6B—C3B | 1.486 (5) |
N2A—C2A | 1.339 (4) | C7B—C1B | 1.490 (4) |
N2A—C17A | 1.396 (4) | C1A—H1A1 | 0.9800 |
N2A—C5A | 1.495 (4) | C1A—H1A2 | 0.9800 |
O4A—C13A | 1.370 (4) | C1A—H1A3 | 0.9800 |
O4A—C16A | 1.417 (4) | C16B—H16A | 0.9800 |
O4B—C13B | 1.372 (4) | C16B—H16B | 0.9800 |
O4B—C16B | 1.426 (4) | C16B—H16C | 0.9800 |
O2A—C3A | 1.341 (4) | C18A—H18A | 0.9800 |
O2A—C8A | 1.447 (3) | C18A—H18B | 0.9800 |
N2B—C2B | 1.336 (4) | C18A—H18C | 0.9800 |
N2B—C17B | 1.395 (4) | C15B—H15A | 0.9800 |
N2B—C5B | 1.501 (4) | C15B—H15B | 0.9800 |
C11A—C12A | 1.380 (4) | C15B—H15C | 0.9800 |
C11A—C10A | 1.395 (4) | C1B—H1B1 | 0.9800 |
C11A—H11A | 0.9500 | C1B—H1B2 | 0.9800 |
O5A—C20A | 1.220 (4) | C1B—H1B3 | 0.9800 |
N1B—C2B | 1.328 (4) | C18B—H18D | 0.9800 |
N1B—C7B | 1.401 (4) | C18B—H18E | 0.9800 |
N1B—H1B | 0.8800 | C18B—H18F | 0.9800 |
C9A—C10A | 1.377 (4) | C15A—H15D | 0.9800 |
C9A—C14A | 1.400 (4) | C15A—H15E | 0.9800 |
C9A—C5A | 1.520 (4) | C15A—H15F | 0.9800 |
O5B—C20B | 1.229 (4) | O2B—C3B | 1.339 (4) |
C14A—C13A | 1.376 (4) | O2B—C8B | 1.449 (4) |
C14A—H14A | 0.9500 | O1B—C3B | 1.192 (4) |
O1A—C3A | 1.204 (4) | C16A—H16D | 0.9800 |
C11B—C12B | 1.379 (4) | C16A—H16E | 0.9800 |
C11B—C10B | 1.392 (4) | C16A—H16F | 0.9800 |
C11B—H11B | 0.9500 | C21A—H21D | 0.9800 |
C13B—C14B | 1.378 (4) | C21A—H21E | 0.9800 |
C13B—C12B | 1.399 (4) | C21A—H21F | 0.9800 |
C10A—H10A | 0.9500 | C8A—C4A | 1.504 (4) |
C17B—C19B | 1.356 (4) | C8A—H8A1 | 0.9900 |
C17B—C18B | 1.485 (4) | C8A—H8A2 | 0.9900 |
C5A—C6A | 1.510 (4) | C4A—H4A1 | 0.9800 |
C5A—H5A | 1.0000 | C4A—H4A2 | 0.9800 |
C9B—C10B | 1.385 (4) | C4A—H4A3 | 0.9800 |
C9B—C14B | 1.399 (4) | C8B—C4B' | 1.259 (16) |
C9B—C5B | 1.517 (4) | C8B—C4B | 1.411 (9) |
C19B—C20B | 1.485 (4) | C8B—H8B1 | 0.9900 |
C6A—C7A | 1.347 (4) | C8B—H8B2 | 0.9900 |
C6A—C3A | 1.478 (4) | C4B—H4B1 | 0.9800 |
C21B—C20B | 1.488 (4) | C4B—H4B2 | 0.9800 |
C21B—H21A | 0.9800 | C4B—H4B3 | 0.9800 |
C21B—H21B | 0.9800 | C4B'—H4B4 | 0.9800 |
C21B—H21C | 0.9800 | C4B'—H4B5 | 0.9800 |
C14B—H14B | 0.9500 | C4B'—H4B6 | 0.9800 |
C2A—S1A—C19A | 89.49 (15) | O1A—C3A—C6A | 126.9 (3) |
C2B—S1B—C19B | 88.95 (16) | O2A—C3A—C6A | 110.1 (3) |
C12B—O3B—C15B | 118.0 (2) | C7B—C6B—C3B | 120.8 (3) |
C12A—O3A—C15A | 118.4 (3) | C7B—C6B—C5B | 122.6 (3) |
C2A—N1A—C7A | 121.1 (3) | C3B—C6B—C5B | 116.5 (3) |
C2A—N1A—H1A | 119.5 | C6B—C7B—N1B | 118.5 (3) |
C7A—N1A—H1A | 119.5 | C6B—C7B—C1B | 128.0 (3) |
C2A—N2A—C17A | 113.5 (3) | N1B—C7B—C1B | 113.5 (3) |
C2A—N2A—C5A | 121.4 (3) | C7A—C1A—H1A1 | 109.5 |
C17A—N2A—C5A | 124.7 (3) | C7A—C1A—H1A2 | 109.5 |
C13A—O4A—C16A | 117.1 (3) | H1A1—C1A—H1A2 | 109.5 |
C13B—O4B—C16B | 117.6 (3) | C7A—C1A—H1A3 | 109.5 |
C3A—O2A—C8A | 116.4 (3) | H1A1—C1A—H1A3 | 109.5 |
C2B—N2B—C17B | 113.9 (3) | H1A2—C1A—H1A3 | 109.5 |
C2B—N2B—C5B | 120.8 (3) | C17A—C19A—C20A | 133.4 (3) |
C17B—N2B—C5B | 124.2 (3) | C17A—C19A—S1A | 112.3 (3) |
C12A—C11A—C10A | 119.2 (3) | C20A—C19A—S1A | 114.3 (2) |
C12A—C11A—H11A | 120.4 | O4B—C16B—H16A | 109.5 |
C10A—C11A—H11A | 120.4 | O4B—C16B—H16B | 109.5 |
C2B—N1B—C7B | 121.2 (3) | H16A—C16B—H16B | 109.5 |
C2B—N1B—H1B | 119.4 | O4B—C16B—H16C | 109.5 |
C7B—N1B—H1B | 119.4 | H16A—C16B—H16C | 109.5 |
C10A—C9A—C14A | 119.6 (3) | H16B—C16B—H16C | 109.5 |
C10A—C9A—C5A | 120.4 (3) | C17A—C18A—H18A | 109.5 |
C14A—C9A—C5A | 119.9 (3) | C17A—C18A—H18B | 109.5 |
C13A—C14A—C9A | 119.9 (3) | H18A—C18A—H18B | 109.5 |
C13A—C14A—H14A | 120.0 | C17A—C18A—H18C | 109.5 |
C9A—C14A—H14A | 120.0 | H18A—C18A—H18C | 109.5 |
C12B—C11B—C10B | 120.1 (3) | H18B—C18A—H18C | 109.5 |
C12B—C11B—H11B | 120.0 | O3B—C15B—H15A | 109.5 |
C10B—C11B—H11B | 120.0 | O3B—C15B—H15B | 109.5 |
O4B—C13B—C14B | 124.8 (3) | H15A—C15B—H15B | 109.5 |
O4B—C13B—C12B | 115.0 (3) | O3B—C15B—H15C | 109.5 |
C14B—C13B—C12B | 120.2 (3) | H15A—C15B—H15C | 109.5 |
C9A—C10A—C11A | 120.8 (3) | H15B—C15B—H15C | 109.5 |
C9A—C10A—H10A | 119.6 | C7B—C1B—H1B1 | 109.5 |
C11A—C10A—H10A | 119.6 | C7B—C1B—H1B2 | 109.5 |
N1B—C2B—N2B | 121.8 (3) | H1B1—C1B—H1B2 | 109.5 |
N1B—C2B—S1B | 124.8 (3) | C7B—C1B—H1B3 | 109.5 |
N2B—C2B—S1B | 113.4 (2) | H1B1—C1B—H1B3 | 109.5 |
C19B—C17B—N2B | 110.8 (3) | H1B2—C1B—H1B3 | 109.5 |
C19B—C17B—C18B | 128.9 (3) | C17B—C18B—H18D | 109.5 |
N2B—C17B—C18B | 120.3 (3) | C17B—C18B—H18E | 109.5 |
N2A—C5A—C6A | 109.0 (2) | H18D—C18B—H18E | 109.5 |
N2A—C5A—C9A | 109.4 (2) | C17B—C18B—H18F | 109.5 |
C6A—C5A—C9A | 113.1 (3) | H18D—C18B—H18F | 109.5 |
N2A—C5A—H5A | 108.4 | H18E—C18B—H18F | 109.5 |
C6A—C5A—H5A | 108.4 | O3A—C15A—H15D | 109.5 |
C9A—C5A—H5A | 108.4 | O3A—C15A—H15E | 109.5 |
C10B—C9B—C14B | 119.3 (3) | H15D—C15A—H15E | 109.5 |
C10B—C9B—C5B | 121.5 (3) | O3A—C15A—H15F | 109.5 |
C14B—C9B—C5B | 119.2 (3) | H15D—C15A—H15F | 109.5 |
C17B—C19B—C20B | 133.4 (3) | H15E—C15A—H15F | 109.5 |
C17B—C19B—S1B | 112.9 (3) | C3B—O2B—C8B | 116.9 (3) |
C20B—C19B—S1B | 113.6 (2) | O4A—C16A—H16D | 109.5 |
C7A—C6A—C3A | 120.8 (3) | O4A—C16A—H16E | 109.5 |
C7A—C6A—C5A | 122.6 (3) | H16D—C16A—H16E | 109.5 |
C3A—C6A—C5A | 116.5 (3) | O4A—C16A—H16F | 109.5 |
N1A—C2A—N2A | 122.3 (3) | H16D—C16A—H16F | 109.5 |
N1A—C2A—S1A | 124.5 (2) | H16E—C16A—H16F | 109.5 |
N2A—C2A—S1A | 113.2 (2) | C20A—C21A—H21D | 109.5 |
C20B—C21B—H21A | 109.5 | C20A—C21A—H21E | 109.5 |
C20B—C21B—H21B | 109.5 | H21D—C21A—H21E | 109.5 |
H21A—C21B—H21B | 109.5 | C20A—C21A—H21F | 109.5 |
C20B—C21B—H21C | 109.5 | H21D—C21A—H21F | 109.5 |
H21A—C21B—H21C | 109.5 | H21E—C21A—H21F | 109.5 |
H21B—C21B—H21C | 109.5 | O2A—C8A—C4A | 105.8 (3) |
C13B—C14B—C9B | 120.2 (3) | O2A—C8A—H8A1 | 110.6 |
C13B—C14B—H14B | 119.9 | C4A—C8A—H8A1 | 110.6 |
C9B—C14B—H14B | 119.9 | O2A—C8A—H8A2 | 110.6 |
O3A—C12A—C11A | 124.6 (3) | C4A—C8A—H8A2 | 110.6 |
O3A—C12A—C13A | 115.0 (3) | H8A1—C8A—H8A2 | 108.7 |
C11A—C12A—C13A | 120.4 (3) | C8A—C4A—H4A1 | 109.5 |
O4A—C13A—C14A | 124.7 (3) | C8A—C4A—H4A2 | 109.5 |
O4A—C13A—C12A | 115.2 (3) | H4A1—C4A—H4A2 | 109.5 |
C14A—C13A—C12A | 120.0 (3) | C8A—C4A—H4A3 | 109.5 |
O3B—C12B—C11B | 125.3 (3) | H4A1—C4A—H4A3 | 109.5 |
O3B—C12B—C13B | 114.9 (3) | H4A2—C4A—H4A3 | 109.5 |
C11B—C12B—C13B | 119.7 (3) | O1B—C3B—O2B | 123.3 (4) |
C19A—C17A—N2A | 111.1 (3) | O1B—C3B—C6B | 126.1 (4) |
C19A—C17A—C18A | 129.0 (3) | O2B—C3B—C6B | 110.5 (3) |
N2A—C17A—C18A | 119.8 (3) | C4B'—C8B—C4B | 43.9 (13) |
O5A—C20A—C19A | 117.3 (3) | C4B'—C8B—O2B | 117.6 (8) |
O5A—C20A—C21A | 122.3 (3) | C4B—C8B—O2B | 110.9 (4) |
C19A—C20A—C21A | 120.3 (3) | C4B'—C8B—H8B1 | 66.5 |
C6A—C7A—N1A | 119.4 (3) | C4B—C8B—H8B1 | 109.5 |
C6A—C7A—C1A | 128.0 (3) | O2B—C8B—H8B1 | 109.5 |
N1A—C7A—C1A | 112.6 (3) | C4B'—C8B—H8B2 | 131.7 |
C9B—C10B—C11B | 120.5 (3) | C4B—C8B—H8B2 | 109.5 |
C9B—C10B—H10B | 119.8 | O2B—C8B—H8B2 | 109.5 |
C11B—C10B—H10B | 119.8 | H8B1—C8B—H8B2 | 108.0 |
N2B—C5B—C6B | 108.0 (3) | C8B—C4B—H4B1 | 109.5 |
N2B—C5B—C9B | 109.2 (2) | C8B—C4B—H4B2 | 109.5 |
C6B—C5B—C9B | 113.9 (3) | C8B—C4B—H4B3 | 109.5 |
N2B—C5B—H5B | 108.5 | C8B—C4B'—H4B4 | 109.5 |
C6B—C5B—H5B | 108.5 | C8B—C4B'—H4B5 | 109.5 |
C9B—C5B—H5B | 108.5 | H4B4—C4B'—H4B5 | 109.5 |
O5B—C20B—C19B | 116.9 (3) | C8B—C4B'—H4B6 | 109.5 |
O5B—C20B—C21B | 122.5 (3) | H4B4—C4B'—H4B6 | 109.5 |
C19B—C20B—C21B | 120.6 (3) | H4B5—C4B'—H4B6 | 109.5 |
O1A—C3A—O2A | 123.0 (3) | ||
C10A—C9A—C14A—C13A | −0.1 (5) | O4B—C13B—C12B—O3B | −2.2 (4) |
C5A—C9A—C14A—C13A | −179.8 (3) | C14B—C13B—C12B—O3B | 178.0 (3) |
C16B—O4B—C13B—C14B | 7.6 (4) | O4B—C13B—C12B—C11B | 179.1 (3) |
C16B—O4B—C13B—C12B | −172.3 (3) | C14B—C13B—C12B—C11B | −0.8 (5) |
C14A—C9A—C10A—C11A | 1.2 (5) | C2A—N2A—C17A—C19A | −6.3 (4) |
C5A—C9A—C10A—C11A | −179.1 (3) | C5A—N2A—C17A—C19A | 166.5 (3) |
C12A—C11A—C10A—C9A | −0.3 (5) | C2A—N2A—C17A—C18A | 170.4 (3) |
C7B—N1B—C2B—N2B | −9.0 (5) | C5A—N2A—C17A—C18A | −16.7 (5) |
C7B—N1B—C2B—S1B | 168.6 (2) | C3A—C6A—C7A—N1A | −179.4 (3) |
C17B—N2B—C2B—N1B | 176.7 (3) | C5A—C6A—C7A—N1A | −2.3 (5) |
C5B—N2B—C2B—N1B | −14.4 (5) | C3A—C6A—C7A—C1A | 1.8 (5) |
C17B—N2B—C2B—S1B | −1.1 (4) | C5A—C6A—C7A—C1A | 178.9 (3) |
C5B—N2B—C2B—S1B | 167.7 (2) | C2A—N1A—C7A—C6A | −10.8 (5) |
C19B—S1B—C2B—N1B | −178.0 (3) | C2A—N1A—C7A—C1A | 168.1 (3) |
C19B—S1B—C2B—N2B | −0.2 (3) | C14B—C9B—C10B—C11B | −0.6 (5) |
C2B—N2B—C17B—C19B | 2.3 (4) | C5B—C9B—C10B—C11B | −179.5 (3) |
C5B—N2B—C17B—C19B | −166.1 (3) | C12B—C11B—C10B—C9B | −0.5 (5) |
C2B—N2B—C17B—C18B | −175.7 (3) | C2B—N2B—C5B—C6B | 28.3 (4) |
C5B—N2B—C17B—C18B | 15.9 (4) | C17B—N2B—C5B—C6B | −164.0 (3) |
C2A—N2A—C5A—C6A | −22.7 (4) | C2B—N2B—C5B—C9B | −96.1 (3) |
C17A—N2A—C5A—C6A | 164.9 (3) | C17B—N2B—C5B—C9B | 71.6 (4) |
C2A—N2A—C5A—C9A | 101.4 (3) | C10B—C9B—C5B—N2B | 70.5 (4) |
C17A—N2A—C5A—C9A | −70.9 (4) | C14B—C9B—C5B—N2B | −108.3 (3) |
C10A—C9A—C5A—N2A | −70.4 (4) | C10B—C9B—C5B—C6B | −50.4 (4) |
C14A—C9A—C5A—N2A | 109.3 (3) | C14B—C9B—C5B—C6B | 130.8 (3) |
C10A—C9A—C5A—C6A | 51.4 (4) | C17B—C19B—C20B—O5B | 171.4 (3) |
C14A—C9A—C5A—C6A | −128.9 (3) | S1B—C19B—C20B—O5B | −5.7 (4) |
N2B—C17B—C19B—C20B | −179.4 (3) | C17B—C19B—C20B—C21B | −9.5 (6) |
C18B—C17B—C19B—C20B | −1.6 (6) | S1B—C19B—C20B—C21B | 173.4 (2) |
N2B—C17B—C19B—S1B | −2.4 (4) | C8A—O2A—C3A—O1A | 1.1 (5) |
C18B—C17B—C19B—S1B | 175.4 (3) | C8A—O2A—C3A—C6A | −177.9 (3) |
C2B—S1B—C19B—C17B | 1.5 (3) | C7A—C6A—C3A—O1A | 12.5 (5) |
C2B—S1B—C19B—C20B | 179.2 (3) | C5A—C6A—C3A—O1A | −164.8 (3) |
N2A—C5A—C6A—C7A | 17.6 (4) | C7A—C6A—C3A—O2A | −168.6 (3) |
C9A—C5A—C6A—C7A | −104.3 (3) | C5A—C6A—C3A—O2A | 14.1 (4) |
N2A—C5A—C6A—C3A | −165.2 (3) | N2B—C5B—C6B—C7B | −23.1 (4) |
C9A—C5A—C6A—C3A | 72.9 (3) | C9B—C5B—C6B—C7B | 98.5 (4) |
C7A—N1A—C2A—N2A | 5.6 (5) | N2B—C5B—C6B—C3B | 156.1 (3) |
C7A—N1A—C2A—S1A | −173.7 (2) | C9B—C5B—C6B—C3B | −82.4 (4) |
C17A—N2A—C2A—N1A | −174.1 (3) | C3B—C6B—C7B—N1B | −175.3 (3) |
C5A—N2A—C2A—N1A | 12.8 (5) | C5B—C6B—C7B—N1B | 3.8 (5) |
C17A—N2A—C2A—S1A | 5.3 (4) | C3B—C6B—C7B—C1B | 2.9 (5) |
C5A—N2A—C2A—S1A | −167.9 (2) | C5B—C6B—C7B—C1B | −178.0 (3) |
C19A—S1A—C2A—N1A | 177.2 (3) | C2B—N1B—C7B—C6B | 14.3 (5) |
C19A—S1A—C2A—N2A | −2.2 (3) | C2B—N1B—C7B—C1B | −164.2 (3) |
O4B—C13B—C14B—C9B | 179.8 (3) | N2A—C17A—C19A—C20A | −177.7 (3) |
C12B—C13B—C14B—C9B | −0.3 (5) | C18A—C17A—C19A—C20A | 5.9 (6) |
C10B—C9B—C14B—C13B | 1.0 (5) | N2A—C17A—C19A—S1A | 4.6 (4) |
C5B—C9B—C14B—C13B | 179.9 (3) | C18A—C17A—C19A—S1A | −171.8 (3) |
C15A—O3A—C12A—C11A | 8.8 (5) | O5A—C20A—C19A—C17A | −178.0 (3) |
C15A—O3A—C12A—C13A | −172.5 (3) | C21A—C20A—C19A—C17A | 4.3 (6) |
C10A—C11A—C12A—O3A | 177.0 (3) | O5A—C20A—C19A—S1A | −0.3 (4) |
C10A—C11A—C12A—C13A | −1.7 (5) | C21A—C20A—C19A—S1A | −178.1 (3) |
C16A—O4A—C13A—C14A | −7.3 (5) | C2A—S1A—C19A—C17A | −1.5 (3) |
C16A—O4A—C13A—C12A | 174.0 (3) | C2A—S1A—C19A—C20A | −179.7 (3) |
C9A—C14A—C13A—O4A | 179.5 (3) | C3A—O2A—C8A—C4A | 177.7 (3) |
C9A—C14A—C13A—C12A | −1.9 (5) | C8B—O2B—C3B—O1B | 3.4 (6) |
O3A—C12A—C13A—O4A | 2.8 (4) | C8B—O2B—C3B—C6B | −176.6 (3) |
C11A—C12A—C13A—O4A | −178.5 (3) | C7B—C6B—C3B—O1B | −13.9 (6) |
O3A—C12A—C13A—C14A | −176.0 (3) | C5B—C6B—C3B—O1B | 166.9 (3) |
C11A—C12A—C13A—C14A | 2.8 (5) | C7B—C6B—C3B—O2B | 166.1 (3) |
C15B—O3B—C12B—C11B | −10.9 (4) | C5B—C6B—C3B—O2B | −13.0 (4) |
C15B—O3B—C12B—C13B | 170.4 (3) | C3B—O2B—C8B—C4B' | 160 (2) |
C10B—C11B—C12B—O3B | −177.4 (3) | C3B—O2B—C8B—C4B | 112.4 (8) |
C10B—C11B—C12B—C13B | 1.2 (5) |
Cg3 is the centroid of the C9B–C14B ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···Cl1A | 0.88 | 2.20 | 2.993 (1) | 151 |
N1B—H1B···Cl1Bi | 0.88 | 2.20 | 2.992 (2) | 150 |
C11A—H11A···O5Bii | 0.95 | 2.58 | 3.523 (1) | 173 |
C15B—H15C···O5Aiii | 0.98 | 2.58 | 3.456 (6) | 148 |
C21A—H21D···O3Biii | 0.98 | 2.50 | 3.459 (6) | 166 |
C4A—H4A2···Cg3 | 0.98 | 2.63 | 3.551 (2) | 157 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+2, −y+1, −z. |
Cg3 is the centroid of the C9B–C14B ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···Cl1A | 0.88 | 2.20 | 2.993 (1) | 151 |
N1B—H1B···Cl1Bi | 0.88 | 2.20 | 2.992 (2) | 150 |
C11A—H11A···O5Bii | 0.95 | 2.58 | 3.523 (1) | 173 |
C15B—H15C···O5Aiii | 0.98 | 2.58 | 3.456 (6) | 148 |
C21A—H21D···O3Biii | 0.98 | 2.50 | 3.459 (6) | 166 |
C4A—H4A2···Cg3 | 0.98 | 2.63 | 3.551 (2) | 157 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+2, −y+1, −z. |
Acknowledgements
NLP thanks for the University Grants Commission (UGC), India, for a CSIR–NET fellowship and MSK thanks the UGC for a UGC–BSR Meritorious fellowship.
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Pyrimidine derivatives are of interest because of their useful biological and therapeutic activities (Ashok et al., 2007). The presence of both pyrimidine and thiazole rings results in enhanced activity (Alam et al., 2010; Kulakov et al., 2009). Thiazolo [3,2-a]pyrimidine derivatives generate enzyme inhibitors as novel therapeutical entities for severe neurodegenerative diseases (Zhi et al., 2008). In continuation to our research interests on thiazolo[3,2-a]pyrimidine derivatives (Prasad et al., 2014; Nagarajaiah et al., 2012), we report the crystal structure of the title compound. During the synthesis of one of the thiazolopyrimidine derivatives, an intermediate [C21H25N2O5S]+ Cl- (I) was isolated and the structure was confirmed by X-ray diffraction.
The molecular structure of the compound is shown in Fig. 1. The title compound, [C21H25N2O5S]+ Cl-, crystallizes in the triclinic space group with two molecules in the asymmetric unit. In molecules A and B, the 3,4- dimethoxy substituted phenyl ring form dihedral angle of 88.38 (7)° / 89.97 (3)° with mean plane of the pyrimidine ring and 6.79 (8)° / 6.42 (7)° with thiazole ring respectively. The two values separated by / corresponds to the two molecules in the asymmetric unit. The pyrimidine ring adopts a sofa conformation with atom C5A displaced by -0.2637 (3) Å from the mean plane of the other five atoms (N1A/C2A/N2A/C6A/C7A). The carbonyl group of the exocyclic ester at C6A and C6B adopts a cis orientation with respect to C6A=C7A and C6B=C6B double bond and the 3,4-dimethoxy substituted phenyl ring shows an syn periplanar conformation with respect to C5A—H5A and C5B—H5B bond of the pyrimidine ring. Phenyl ring at C5A and C5B in both the molecules shows antagonist (aryl-group up) conformation (Rovnyak et al., 1995). The packing features C—H···O interactions. The weak C11A—H11A···O5B hydrogen bonds forms supramolecular assembly along the crystallographic [101], which are inturn linked by another two C—H···O interactions (C15B—H15C···O5A & C21A—H21D···O3B) resulting in a ring with the graph set R22(7) notation (Table. 1; Fig. 2). The crystal packing also features N1A—H1A···Cl1A & N1B—H1B···Cl1B interactions. In addition, a weak C—H···π interaction of the type C4A-H4A2···Cg (Cg being the centroid of the phenyl ring) at a distance of 2.628 Å is also observed (Fig. 3).