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Derivatives of pyrimidine-2(1H)-selenone are a group of com­pounds with very strong anti­microbial activity. In order to study the effect of the position of the meth­oxy substituent on biological activity, mol­ecular geometry and inter­molecular inter­actions in the crystal, three derivatives were prepared and evaluated with respect to their anti­microbial activities, and their crystal structures were determined by X-ray diffraction. The investigated com­pounds, namely, 1-(X-meth­oxy­phen­yl)-4-methyl-6-phenyl­pyrimidine-2(1H)-seleno­nes (X = 2, 3 and 4 for 1, 2 and 3, respectively), C18H16N2OSe, showed very strong activity against selected strains of Gram-positive bacteria and fungi. Two com­pounds, 1 and 2, crystallize in the monoclinic space group P21/c, while 3 crystallizes in the space group P21/n; 1 has two mol­ecules in the asymmetric unit and the other two (2 and 3) have one mol­ecule. The geometries of the investigated com­pounds differ slightly in the mutual orientations of the aromatic and pyrimidine­selenone rings. The O atom in 1 stabilizes the conformation of the mol­ecules via intra­molecular C—H...O hydrogen bonding. The packing of mol­ecules is determined by weak C—H...N and C—H...Se inter­molecular inter­actions and additionally in 1 and 2 by C—H...O inter­molecular inter­actions. The introduction of the meth­oxy substituent results in greater selectivity of the investigated com­pounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620004040/qs3091sup1.cif
Contains datablocks global, 1, 2, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004040/qs30911sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004040/qs30912sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004040/qs30913sup4.hkl
Contains datablock 3

CCDC references: 1992163; 1992162; 1992161

Computing details top

For all structures, data collection: COLLECT (Bruker, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (1), (3); SIR2014 (Burla et al., 2015) and SHELXS97 (Sheldrick, 2008) for (2). For all structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

4-Methyl-1-(2-methoxyphenyl)-6-phenylpyrimidine-2(1H)-selenone (1) top
Crystal data top
C18H16N2OSeF(000) = 1440
Mr = 355.29Dx = 1.49 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13681 reflections
a = 14.8080 (2) Åθ = 1.0–27.5°
b = 15.6970 (2) ŵ = 2.37 mm1
c = 14.9770 (2) ÅT = 100 K
β = 114.482 (1)°Prism, red
V = 3168.27 (8) Å30.52 × 0.34 × 0.23 mm
Z = 8
Data collection top
Bruker KappaCCD
diffractometer
7239 independent reflections
Horizonally mounted graphite crystal monochromator6200 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm-1Rint = 0.028
CCD scansθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1918
Tmin = 0.915, Tmax = 1.000k = 2020
24786 measured reflectionsl = 1919
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026 w = 1/[σ2(Fo2) + (0.0285P)2 + 2.5089P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.064(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.37 e Å3
7239 reflectionsΔρmin = 0.53 e Å3
402 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.00245 (19)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C2A0.14233 (13)0.57910 (11)0.26337 (12)0.0139 (3)
N3A0.23808 (11)0.58675 (10)0.32912 (11)0.0161 (3)
C4A0.29094 (13)0.65440 (12)0.32716 (13)0.0163 (4)
C5A0.24940 (13)0.72129 (11)0.25984 (13)0.0167 (4)
H5A0.2882750.7694460.2598740.02*
C6A0.15239 (13)0.71582 (11)0.19457 (12)0.0141 (3)
N1A0.09897 (11)0.64468 (9)0.19643 (10)0.0134 (3)
C19A0.39787 (14)0.65545 (13)0.39780 (15)0.0241 (4)
H19A0.4092080.6125920.4489180.036*
H19B0.4151140.711950.4279870.036*
H19C0.4393280.6425080.3627710.036*
C13A0.10486 (13)0.78098 (11)0.11746 (13)0.0160 (3)
C18A0.14401 (14)0.79467 (13)0.04894 (14)0.0221 (4)
H18A0.2014530.7643150.0540680.027*
C17A0.09978 (16)0.85237 (14)0.02692 (15)0.0274 (4)
H17A0.1269570.8613930.0735440.033*
C16A0.01616 (15)0.89679 (13)0.03478 (14)0.0245 (4)
H16A0.0150440.9352130.0877380.029*
C15A0.02210 (16)0.88529 (12)0.03451 (15)0.0241 (4)
H15A0.0787560.9166990.029750.029*
C14A0.02218 (15)0.82794 (12)0.11092 (15)0.0218 (4)
H14A0.0037540.8206320.1587830.026*
C7A0.00353 (13)0.63678 (11)0.12675 (12)0.0138 (3)
C12A0.02640 (13)0.60530 (11)0.03389 (13)0.0163 (3)
H12A0.0249990.587720.0156480.02*
C11A0.12517 (14)0.59943 (12)0.03291 (13)0.0198 (4)
H11A0.1417270.5781080.097160.024*
C10A0.19921 (14)0.62498 (13)0.00482 (14)0.0218 (4)
H10A0.2667260.6203730.0500620.026*
C9A0.17604 (14)0.65737 (12)0.08892 (14)0.0205 (4)
H9A0.2275250.6746910.1071630.025*
C8A0.07774 (13)0.66419 (11)0.15526 (13)0.0164 (4)
O1A0.04479 (10)0.69747 (9)0.24753 (9)0.0202 (3)
C20A0.11766 (16)0.73463 (15)0.27567 (16)0.0280 (5)
H20A0.1532460.7797510.2291660.042*
H20B0.0847030.7588220.3417030.042*
H20C0.1647920.6906790.2753720.042*
C2B0.56860 (13)0.39704 (11)0.07566 (12)0.0138 (3)
N3B0.64735 (11)0.38649 (10)0.05278 (11)0.0162 (3)
C4B0.73440 (13)0.42058 (12)0.10926 (14)0.0178 (4)
C5B0.74847 (13)0.47022 (12)0.19206 (13)0.0179 (4)
H5B0.8103210.4971810.2287060.021*
C6B0.67088 (13)0.47883 (11)0.21869 (12)0.0141 (3)
N1B0.58261 (10)0.43953 (9)0.16222 (10)0.0128 (3)
C19B0.81883 (14)0.40302 (14)0.08134 (16)0.0260 (4)
H19D0.8496150.3484460.1095270.039*
H19E0.8681810.4486340.1065260.039*
H19F0.7939020.4005090.0097130.039*
C13B0.67699 (13)0.53107 (11)0.30397 (13)0.0153 (3)
C18B0.66280 (16)0.61843 (13)0.29220 (14)0.0244 (4)
H18B0.6497330.6438170.230480.029*
C17B0.66757 (18)0.66889 (14)0.37003 (15)0.0298 (5)
H17B0.6570810.7285930.3614520.036*
C16B0.68769 (16)0.63200 (14)0.46033 (14)0.0259 (4)
H16B0.691220.6665840.5137340.031*
C15B0.70250 (17)0.54590 (14)0.47298 (14)0.0292 (5)
H15B0.7164680.5209970.5351290.035*
C14B0.69715 (16)0.49488 (13)0.39509 (14)0.0265 (4)
H14B0.707280.4351690.404080.032*
C7B0.50342 (12)0.44033 (11)0.19531 (12)0.0137 (3)
C12B0.43394 (13)0.50503 (12)0.16678 (13)0.0161 (4)
H12B0.4364740.5490190.1243040.019*
C11B0.35993 (14)0.50443 (12)0.20166 (14)0.0192 (4)
H11B0.3113930.5483120.182770.023*
C10B0.35698 (14)0.44025 (13)0.26357 (14)0.0201 (4)
H10B0.3063820.4405270.2869940.024*
C9B0.42718 (13)0.37523 (12)0.29204 (13)0.0180 (4)
H9B0.4245860.331450.3347050.022*
C8B0.50126 (13)0.37480 (11)0.25754 (13)0.0147 (3)
O1B0.57416 (9)0.31483 (8)0.27973 (9)0.0174 (3)
C20B0.57406 (15)0.24727 (13)0.34408 (15)0.0243 (4)
H20D0.5837240.2710660.4078990.036*
H20E0.6279820.2073970.3526930.036*
H20F0.5104230.2171480.3156260.036*
Se1A0.07334 (2)0.48228 (2)0.26267 (2)0.01922 (6)
Se1B0.44599 (2)0.35690 (2)0.00581 (2)0.01773 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C2A0.0179 (8)0.0131 (8)0.0147 (8)0.0018 (6)0.0106 (7)0.0011 (6)
N3A0.0170 (7)0.0168 (8)0.0167 (7)0.0005 (6)0.0092 (6)0.0014 (6)
C4A0.0179 (9)0.0175 (9)0.0164 (8)0.0003 (7)0.0099 (7)0.0046 (7)
C5A0.0185 (9)0.0137 (9)0.0211 (9)0.0050 (7)0.0114 (7)0.0040 (7)
C6A0.0199 (9)0.0113 (8)0.0162 (8)0.0011 (6)0.0124 (7)0.0026 (7)
N1A0.0153 (7)0.0127 (7)0.0147 (7)0.0017 (5)0.0086 (6)0.0011 (6)
C19A0.0178 (9)0.0259 (10)0.0240 (9)0.0032 (8)0.0040 (8)0.0024 (8)
C13A0.0183 (9)0.0131 (8)0.0174 (8)0.0035 (7)0.0081 (7)0.0018 (7)
C18A0.0203 (9)0.0262 (10)0.0227 (9)0.0002 (8)0.0118 (8)0.0038 (8)
C17A0.0305 (11)0.0344 (12)0.0226 (9)0.0003 (9)0.0163 (9)0.0073 (9)
C16A0.0307 (11)0.0194 (10)0.0210 (9)0.0005 (8)0.0081 (8)0.0046 (8)
C15A0.0295 (11)0.0153 (9)0.0303 (10)0.0046 (8)0.0150 (9)0.0016 (8)
C14A0.0305 (11)0.0150 (9)0.0265 (10)0.0014 (8)0.0185 (8)0.0014 (8)
C7A0.0148 (8)0.0114 (8)0.0160 (8)0.0011 (6)0.0070 (7)0.0014 (6)
C12A0.0196 (9)0.0135 (8)0.0192 (8)0.0002 (7)0.0114 (7)0.0011 (7)
C11A0.0221 (9)0.0189 (9)0.0169 (8)0.0007 (7)0.0067 (7)0.0020 (7)
C10A0.0161 (9)0.0227 (10)0.0231 (9)0.0009 (7)0.0047 (7)0.0003 (8)
C9A0.0185 (9)0.0208 (10)0.0252 (9)0.0035 (7)0.0121 (8)0.0012 (8)
C8A0.0200 (9)0.0145 (8)0.0175 (8)0.0005 (7)0.0106 (7)0.0015 (7)
O1A0.0223 (7)0.0233 (7)0.0192 (6)0.0019 (5)0.0130 (5)0.0044 (5)
C20A0.0315 (11)0.0297 (11)0.0308 (11)0.0092 (9)0.0210 (9)0.0025 (9)
C2B0.0162 (8)0.0119 (8)0.0150 (8)0.0023 (6)0.0083 (7)0.0026 (6)
N3B0.0160 (7)0.0162 (8)0.0193 (7)0.0010 (6)0.0103 (6)0.0007 (6)
C4B0.0177 (9)0.0159 (9)0.0229 (9)0.0024 (7)0.0115 (7)0.0038 (7)
C5B0.0144 (8)0.0196 (9)0.0204 (9)0.0013 (7)0.0081 (7)0.0006 (7)
C6B0.0147 (8)0.0110 (8)0.0153 (8)0.0008 (6)0.0048 (7)0.0027 (6)
N1B0.0123 (7)0.0127 (7)0.0147 (7)0.0002 (5)0.0067 (6)0.0006 (6)
C19B0.0186 (9)0.0324 (12)0.0335 (11)0.0020 (8)0.0172 (8)0.0049 (9)
C13B0.0121 (8)0.0172 (9)0.0149 (8)0.0021 (6)0.0038 (7)0.0012 (7)
C18B0.0359 (11)0.0196 (10)0.0175 (9)0.0028 (8)0.0107 (8)0.0029 (8)
C17B0.0446 (13)0.0188 (10)0.0238 (10)0.0070 (9)0.0121 (9)0.0012 (8)
C16B0.0296 (11)0.0283 (11)0.0182 (9)0.0040 (8)0.0084 (8)0.0063 (8)
C15B0.0409 (12)0.0274 (11)0.0150 (9)0.0064 (9)0.0072 (9)0.0011 (8)
C14B0.0377 (12)0.0179 (10)0.0181 (9)0.0023 (8)0.0057 (8)0.0012 (8)
C7B0.0125 (8)0.0163 (9)0.0141 (8)0.0015 (6)0.0073 (6)0.0041 (7)
C12B0.0175 (9)0.0145 (9)0.0166 (8)0.0006 (7)0.0073 (7)0.0025 (7)
C11B0.0177 (9)0.0197 (9)0.0209 (9)0.0047 (7)0.0087 (7)0.0040 (7)
C10B0.0175 (9)0.0250 (10)0.0223 (9)0.0012 (7)0.0129 (7)0.0073 (8)
C9B0.0189 (9)0.0194 (9)0.0193 (9)0.0011 (7)0.0116 (7)0.0013 (7)
C8B0.0141 (8)0.0155 (9)0.0152 (8)0.0002 (6)0.0067 (7)0.0025 (7)
O1B0.0181 (6)0.0163 (6)0.0224 (6)0.0038 (5)0.0130 (5)0.0050 (5)
C20B0.0266 (10)0.0211 (10)0.0303 (10)0.0050 (8)0.0168 (8)0.0108 (8)
Se1A0.02195 (10)0.01511 (10)0.02205 (10)0.00360 (7)0.01054 (8)0.00195 (7)
Se1B0.01455 (9)0.02195 (10)0.01731 (9)0.00183 (7)0.00721 (7)0.00489 (7)
Geometric parameters (Å, º) top
C2A—N3A1.355 (2)C2B—N3B1.355 (2)
C2A—N1A1.394 (2)C2B—N1B1.395 (2)
C2A—Se1A1.8287 (18)C2B—Se1B1.8292 (17)
N3A—C4A1.327 (2)N3B—C4B1.327 (2)
C4A—C5A1.408 (3)C4B—C5B1.405 (3)
C4A—C19A1.496 (3)C4B—C19B1.499 (2)
C5A—C6A1.365 (3)C5B—C6B1.370 (3)
C5A—H5A0.95C5B—H5B0.95
C6A—N1A1.375 (2)C6B—N1B1.374 (2)
C6A—C13A1.484 (2)C6B—C13B1.489 (2)
N1A—C7A1.448 (2)N1B—C7B1.450 (2)
C19A—H19A0.98C19B—H19D0.98
C19A—H19B0.98C19B—H19E0.98
C19A—H19C0.98C19B—H19F0.98
C13A—C18A1.389 (3)C13B—C18B1.387 (3)
C13A—C14A1.397 (3)C13B—C14B1.392 (3)
C18A—C17A1.387 (3)C18B—C17B1.387 (3)
C18A—H18A0.95C18B—H18B0.95
C17A—C16A1.383 (3)C17B—C16B1.385 (3)
C17A—H17A0.95C17B—H17B0.95
C16A—C15A1.385 (3)C16B—C15B1.370 (3)
C16A—H16A0.95C16B—H16B0.95
C15A—C14A1.389 (3)C15B—C14B1.390 (3)
C15A—H15A0.95C15B—H15B0.95
C14A—H14A0.95C14B—H14B0.95
C7A—C12A1.379 (2)C7B—C12B1.381 (2)
C7A—C8A1.401 (2)C7B—C8B1.397 (2)
C12A—C11A1.391 (3)C12B—C11B1.396 (3)
C12A—H12A0.95C12B—H12B0.95
C11A—C10A1.386 (3)C11B—C10B1.382 (3)
C11A—H11A0.95C11B—H11B0.95
C10A—C9A1.396 (3)C10B—C9B1.392 (3)
C10A—H10A0.95C10B—H10B0.95
C9A—C8A1.385 (3)C9B—C8B1.393 (2)
C9A—H9A0.95C9B—H9B0.95
C8A—O1A1.364 (2)C8B—O1B1.365 (2)
O1A—C20A1.435 (2)O1B—C20B1.433 (2)
C20A—H20A0.98C20B—H20D0.98
C20A—H20B0.98C20B—H20E0.98
C20A—H20C0.98C20B—H20F0.98
N3A—C2A—N1A119.23 (15)N3B—C2B—N1B118.78 (15)
N3A—C2A—Se1A119.44 (13)N3B—C2B—Se1B120.64 (13)
N1A—C2A—Se1A121.32 (13)N1B—C2B—Se1B120.58 (12)
C4A—N3A—C2A120.26 (16)C4B—N3B—C2B120.01 (16)
N3A—C4A—C5A121.73 (17)N3B—C4B—C5B122.41 (16)
N3A—C4A—C19A117.03 (16)N3B—C4B—C19B116.76 (17)
C5A—C4A—C19A121.21 (17)C5B—C4B—C19B120.82 (17)
C6A—C5A—C4A118.92 (16)C6B—C5B—C4B118.43 (17)
C6A—C5A—H5A120.5C6B—C5B—H5B120.8
C4A—C5A—H5A120.5C4B—C5B—H5B120.8
C5A—C6A—N1A118.69 (16)C5B—C6B—N1B118.36 (16)
C5A—C6A—C13A122.22 (16)C5B—C6B—C13B122.95 (16)
N1A—C6A—C13A118.95 (15)N1B—C6B—C13B118.65 (15)
C6A—N1A—C2A121.11 (15)C6B—N1B—C2B121.59 (14)
C6A—N1A—C7A119.67 (14)C6B—N1B—C7B118.91 (14)
C2A—N1A—C7A119.21 (14)C2B—N1B—C7B119.47 (14)
C4A—C19A—H19A109.5C4B—C19B—H19D109.5
C4A—C19A—H19B109.5C4B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C4A—C19A—H19C109.5C4B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C18A—C13A—C14A119.25 (17)C18B—C13B—C14B119.18 (17)
C18A—C13A—C6A118.24 (16)C18B—C13B—C6B118.90 (16)
C14A—C13A—C6A122.51 (16)C14B—C13B—C6B121.92 (17)
C17A—C18A—C13A120.43 (18)C17B—C18B—C13B120.36 (18)
C17A—C18A—H18A119.8C17B—C18B—H18B119.8
C13A—C18A—H18A119.8C13B—C18B—H18B119.8
C16A—C17A—C18A120.08 (18)C16B—C17B—C18B119.8 (2)
C16A—C17A—H17A120C16B—C17B—H17B120.1
C18A—C17A—H17A120C18B—C17B—H17B120.1
C17A—C16A—C15A120.03 (18)C15B—C16B—C17B120.31 (19)
C17A—C16A—H16A120C15B—C16B—H16B119.8
C15A—C16A—H16A120C17B—C16B—H16B119.8
C16A—C15A—C14A120.14 (19)C16B—C15B—C14B120.15 (19)
C16A—C15A—H15A119.9C16B—C15B—H15B119.9
C14A—C15A—H15A119.9C14B—C15B—H15B119.9
C15A—C14A—C13A120.03 (18)C15B—C14B—C13B120.16 (19)
C15A—C14A—H14A120C15B—C14B—H14B119.9
C13A—C14A—H14A120C13B—C14B—H14B119.9
C12A—C7A—C8A121.42 (16)C12B—C7B—C8B121.84 (16)
C12A—C7A—N1A120.23 (16)C12B—C7B—N1B120.31 (16)
C8A—C7A—N1A118.32 (15)C8B—C7B—N1B117.84 (15)
C7A—C12A—C11A119.63 (17)C7B—C12B—C11B118.61 (17)
C7A—C12A—H12A120.2C7B—C12B—H12B120.7
C11A—C12A—H12A120.2C11B—C12B—H12B120.7
C10A—C11A—C12A119.37 (17)C10B—C11B—C12B120.26 (17)
C10A—C11A—H11A120.3C10B—C11B—H11B119.9
C12A—C11A—H11A120.3C12B—C11B—H11B119.9
C11A—C10A—C9A121.00 (17)C11B—C10B—C9B120.86 (17)
C11A—C10A—H10A119.5C11B—C10B—H10B119.6
C9A—C10A—H10A119.5C9B—C10B—H10B119.6
C8A—C9A—C10A119.79 (17)C10B—C9B—C8B119.54 (17)
C8A—C9A—H9A120.1C10B—C9B—H9B120.2
C10A—C9A—H9A120.1C8B—C9B—H9B120.2
O1A—C8A—C9A125.77 (16)O1B—C8B—C9B125.30 (16)
O1A—C8A—C7A115.44 (16)O1B—C8B—C7B115.81 (15)
C9A—C8A—C7A118.77 (16)C9B—C8B—C7B118.89 (16)
C8A—O1A—C20A117.14 (15)C8B—O1B—C20B116.92 (14)
O1A—C20A—H20A109.5O1B—C20B—H20D109.5
O1A—C20A—H20B109.5O1B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
O1A—C20A—H20C109.5O1B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
N1A—C2A—N3A—C4A2.6 (2)N1B—C2B—N3B—C4B3.9 (2)
Se1A—C2A—N3A—C4A176.25 (13)Se1B—C2B—N3B—C4B175.73 (13)
C2A—N3A—C4A—C5A2.1 (3)C2B—N3B—C4B—C5B1.8 (3)
C2A—N3A—C4A—C19A176.11 (16)C2B—N3B—C4B—C19B177.56 (17)
N3A—C4A—C5A—C6A0.5 (3)N3B—C4B—C5B—C6B4.4 (3)
C19A—C4A—C5A—C6A177.65 (16)C19B—C4B—C5B—C6B175.00 (18)
C4A—C5A—C6A—N1A0.6 (2)C4B—C5B—C6B—N1B1.0 (3)
C4A—C5A—C6A—C13A176.21 (16)C4B—C5B—C6B—C13B178.91 (16)
C5A—C6A—N1A—C2A0.0 (2)C5B—C6B—N1B—C2B4.8 (2)
C13A—C6A—N1A—C2A175.82 (15)C13B—C6B—N1B—C2B173.28 (15)
C5A—C6A—N1A—C7A178.91 (15)C5B—C6B—N1B—C7B173.40 (16)
C13A—C6A—N1A—C7A3.1 (2)C13B—C6B—N1B—C7B8.6 (2)
N3A—C2A—N1A—C6A1.6 (2)N3B—C2B—N1B—C6B7.3 (2)
Se1A—C2A—N1A—C6A177.27 (12)Se1B—C2B—N1B—C6B172.30 (13)
N3A—C2A—N1A—C7A179.50 (15)N3B—C2B—N1B—C7B170.82 (15)
Se1A—C2A—N1A—C7A1.7 (2)Se1B—C2B—N1B—C7B9.6 (2)
C5A—C6A—C13A—C18A60.2 (2)C5B—C6B—C13B—C18B82.1 (2)
N1A—C6A—C13A—C18A115.45 (19)N1B—C6B—C13B—C18B95.9 (2)
C5A—C6A—C13A—C14A120.5 (2)C5B—C6B—C13B—C14B97.5 (2)
N1A—C6A—C13A—C14A63.9 (2)N1B—C6B—C13B—C14B84.6 (2)
C14A—C13A—C18A—C17A2.0 (3)C14B—C13B—C18B—C17B0.7 (3)
C6A—C13A—C18A—C17A177.36 (18)C6B—C13B—C18B—C17B179.72 (19)
C13A—C18A—C17A—C16A0.0 (3)C13B—C18B—C17B—C16B0.7 (3)
C18A—C17A—C16A—C15A1.6 (3)C18B—C17B—C16B—C15B0.2 (3)
C17A—C16A—C15A—C14A1.3 (3)C17B—C16B—C15B—C14B0.2 (3)
C16A—C15A—C14A—C13A0.7 (3)C16B—C15B—C14B—C13B0.2 (3)
C18A—C13A—C14A—C15A2.3 (3)C18B—C13B—C14B—C15B0.3 (3)
C6A—C13A—C14A—C15A176.99 (18)C6B—C13B—C14B—C15B179.83 (19)
C6A—N1A—C7A—C12A84.2 (2)C6B—N1B—C7B—C12B91.0 (2)
C2A—N1A—C7A—C12A94.7 (2)C2B—N1B—C7B—C12B90.8 (2)
C6A—N1A—C7A—C8A93.92 (19)C6B—N1B—C7B—C8B88.0 (2)
C2A—N1A—C7A—C8A87.1 (2)C2B—N1B—C7B—C8B90.18 (19)
C8A—C7A—C12A—C11A0.8 (3)C8B—C7B—C12B—C11B0.1 (3)
N1A—C7A—C12A—C11A178.89 (16)N1B—C7B—C12B—C11B178.81 (16)
C7A—C12A—C11A—C10A0.3 (3)C7B—C12B—C11B—C10B0.1 (3)
C12A—C11A—C10A—C9A0.8 (3)C12B—C11B—C10B—C9B0.1 (3)
C11A—C10A—C9A—C8A0.1 (3)C11B—C10B—C9B—C8B0.1 (3)
C10A—C9A—C8A—O1A177.46 (18)C10B—C9B—C8B—O1B179.90 (17)
C10A—C9A—C8A—C7A1.1 (3)C10B—C9B—C8B—C7B0.3 (3)
C12A—C7A—C8A—O1A177.15 (16)C12B—C7B—C8B—O1B179.85 (16)
N1A—C7A—C8A—O1A0.9 (2)N1B—C7B—C8B—O1B1.2 (2)
C12A—C7A—C8A—C9A1.5 (3)C12B—C7B—C8B—C9B0.4 (3)
N1A—C7A—C8A—C9A179.62 (16)N1B—C7B—C8B—C9B178.60 (15)
C9A—C8A—O1A—C20A5.1 (3)C9B—C8B—O1B—C20B0.2 (3)
C7A—C8A—O1A—C20A173.46 (16)C7B—C8B—O1B—C20B179.52 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O1Bi0.952.453.258 (2)143
C9A—H9A···Se1Bii0.952.993.6681 (19)129
C17A—H17A···N3Aiii0.952.743.663 (2)165
C19A—H19B···Se1Bi0.982.963.855 (2)152
C12B—H12B···N3Biv0.952.623.447 (2)146
C15B—H15B···N3Av0.952.513.425 (3)161
C18B—H18B···Se1Biv0.953.063.9263 (19)152
C19B—H19E···Se1Avi0.983.013.827 (2)141
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x, y+3/2, z1/2; (iv) x+1, y+1, z; (v) x+1, y+1, z+1; (vi) x+1, y, z.
4-Methyl-1-(3-methoxyphenyl)-6-phenylpyrimidine-2(1H)-selenone (2) top
Crystal data top
C18H16N2OSeF(000) = 720
Mr = 355.29Dx = 1.521 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6409 reflections
a = 9.4670 (6) Åθ = 1.0–27.5°
b = 10.3070 (7) ŵ = 2.42 mm1
c = 16.6150 (9) ÅT = 293 K
β = 106.887 (4)°Block, orange
V = 1551.32 (17) Å30.28 × 0.09 × 0.04 mm
Z = 4
Data collection top
Bruker KappaCCD
diffractometer
3562 independent reflections
Horizonally mounted graphite crystal monochromator2778 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm-1Rint = 0.065
CCD scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1212
Tmin = 0.743, Tmax = 1.000k = 1313
11675 measured reflectionsl = 2121
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0216P)2 + 3.2907P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100(Δ/σ)max < 0.001
S = 1.11Δρmax = 0.87 e Å3
3562 reflectionsΔρmin = 0.66 e Å3
202 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0024 (5)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C20.1813 (4)0.5822 (3)0.5281 (2)0.0223 (7)
N30.1369 (3)0.6656 (3)0.46276 (18)0.0244 (6)
C40.1464 (4)0.6313 (4)0.3872 (2)0.0260 (7)
C50.2033 (4)0.5115 (3)0.3723 (2)0.0237 (7)
H50.2050010.4887160.3184030.028*
C60.2561 (4)0.4289 (3)0.4381 (2)0.0212 (7)
N10.2475 (3)0.4652 (3)0.51637 (17)0.0210 (6)
C190.0951 (5)0.7282 (4)0.3183 (2)0.0388 (10)
H19A0.0092620.7414220.3068930.058*
H19B0.1156940.6967480.2684720.058*
H19C0.1457610.8089070.3350350.058*
C130.3230 (4)0.3019 (3)0.4265 (2)0.0227 (7)
C140.2362 (5)0.2122 (4)0.3720 (2)0.0316 (8)
H140.1367850.2298410.3467360.038*
C150.2959 (5)0.0967 (4)0.3550 (3)0.0397 (10)
H150.2368770.0368540.3183550.048*
C160.4446 (5)0.0702 (4)0.3928 (3)0.0378 (10)
H160.4850680.0077450.381960.045*
C170.5319 (5)0.1601 (4)0.4466 (2)0.0342 (9)
H170.6315560.1428630.4711930.041*
C180.4722 (4)0.2754 (4)0.4641 (2)0.0278 (8)
H180.5312970.3350730.5007860.033*
C70.3074 (4)0.3784 (3)0.5877 (2)0.0241 (7)
C80.2319 (4)0.2664 (3)0.5924 (2)0.0251 (7)
H80.1412410.2486090.5536370.03*
C90.2965 (4)0.1796 (3)0.6580 (2)0.0275 (8)
C100.4311 (4)0.2092 (3)0.7155 (2)0.0303 (8)
H100.4730190.1513850.7588260.036*
C110.5036 (4)0.3229 (4)0.7093 (2)0.0293 (8)
H110.5935160.3416460.7485820.035*
C120.4421 (4)0.4100 (3)0.6443 (2)0.0251 (8)
H120.490160.4868340.6390240.03*
O10.2341 (3)0.0635 (3)0.66904 (17)0.0352 (6)
C200.1217 (5)0.0147 (4)0.5977 (3)0.0385 (10)
H20A0.0347970.0674950.5881490.058*
H20B0.0984180.0730870.6083650.058*
H20C0.1565910.0171740.5489910.058*
Se10.15424 (5)0.62264 (4)0.62984 (2)0.02975 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0255 (17)0.0178 (15)0.0271 (18)0.0009 (14)0.0130 (14)0.0004 (13)
N30.0275 (15)0.0212 (14)0.0261 (15)0.0032 (12)0.0104 (13)0.0036 (11)
C40.0282 (18)0.0247 (17)0.0267 (17)0.0033 (16)0.0103 (14)0.0037 (15)
C50.0283 (19)0.0232 (17)0.0217 (17)0.0014 (15)0.0104 (15)0.0006 (13)
C60.0229 (17)0.0206 (16)0.0226 (17)0.0015 (14)0.0104 (14)0.0003 (13)
N10.0250 (15)0.0172 (13)0.0228 (14)0.0019 (12)0.0100 (12)0.0017 (11)
C190.049 (3)0.038 (2)0.031 (2)0.015 (2)0.0146 (19)0.0116 (17)
C130.0305 (18)0.0193 (16)0.0223 (17)0.0013 (15)0.0141 (15)0.0024 (13)
C140.037 (2)0.029 (2)0.030 (2)0.0012 (17)0.0115 (17)0.0021 (15)
C150.059 (3)0.024 (2)0.038 (2)0.0064 (18)0.018 (2)0.0088 (16)
C160.061 (3)0.0201 (18)0.040 (2)0.0108 (19)0.027 (2)0.0032 (17)
C170.042 (2)0.032 (2)0.031 (2)0.0106 (17)0.0145 (18)0.0001 (16)
C180.033 (2)0.0270 (18)0.0256 (18)0.0038 (16)0.0121 (16)0.0002 (15)
C70.0339 (19)0.0197 (15)0.0226 (16)0.0091 (16)0.0143 (14)0.0018 (14)
C80.0280 (19)0.0244 (18)0.0255 (18)0.0017 (15)0.0118 (15)0.0034 (14)
C90.040 (2)0.0215 (17)0.0269 (19)0.0028 (16)0.0189 (17)0.0001 (14)
C100.043 (2)0.0215 (18)0.032 (2)0.0043 (16)0.0185 (18)0.0010 (15)
C110.034 (2)0.0286 (19)0.0239 (18)0.0047 (16)0.0071 (16)0.0010 (14)
C120.0326 (19)0.0203 (17)0.0251 (18)0.0003 (14)0.0125 (15)0.0023 (13)
O10.0471 (17)0.0246 (13)0.0347 (15)0.0018 (13)0.0130 (13)0.0054 (11)
C200.050 (3)0.0221 (19)0.043 (2)0.0059 (18)0.014 (2)0.0023 (17)
Se10.0422 (2)0.02427 (19)0.02738 (19)0.00485 (18)0.01730 (15)0.00053 (16)
Geometric parameters (Å, º) top
C2—N31.353 (4)C16—C171.382 (6)
C2—N11.399 (4)C16—H160.93
C2—Se11.829 (3)C17—C181.382 (5)
N3—C41.332 (4)C17—H170.93
C4—C51.398 (5)C18—H180.93
C4—C191.491 (5)C7—C81.372 (5)
C5—C61.361 (5)C7—C121.385 (5)
C5—H50.93C8—C91.405 (5)
C6—N11.379 (4)C8—H80.93
C6—C131.492 (5)C9—O11.371 (4)
N1—C71.462 (4)C9—C101.386 (5)
C19—H19A0.96C10—C111.377 (5)
C19—H19B0.96C10—H100.93
C19—H19C0.96C11—C121.396 (5)
C13—C141.384 (5)C11—H110.93
C13—C181.395 (5)C12—H120.93
C14—C151.382 (5)O1—C201.434 (5)
C14—H140.93C20—H20A0.96
C15—C161.392 (6)C20—H20B0.96
C15—H150.93C20—H20C0.96
N3—C2—N1118.9 (3)C15—C16—H16120.1
N3—C2—Se1120.2 (2)C16—C17—C18120.5 (4)
N1—C2—Se1120.9 (2)C16—C17—H17119.7
C4—N3—C2119.9 (3)C18—C17—H17119.7
N3—C4—C5122.5 (3)C17—C18—C13119.7 (4)
N3—C4—C19116.8 (3)C17—C18—H18120.1
C5—C4—C19120.8 (3)C13—C18—H18120.1
C6—C5—C4118.7 (3)C8—C7—C12123.5 (3)
C6—C5—H5120.6C8—C7—N1118.4 (3)
C4—C5—H5120.6C12—C7—N1118.0 (3)
C5—C6—N1118.7 (3)C7—C8—C9117.6 (3)
C5—C6—C13121.1 (3)C7—C8—H8121.2
N1—C6—C13120.3 (3)C9—C8—H8121.2
C6—N1—C2121.2 (3)O1—C9—C10116.5 (3)
C6—N1—C7118.9 (3)O1—C9—C8123.5 (3)
C2—N1—C7119.9 (3)C10—C9—C8120.0 (3)
C4—C19—H19A109.5C11—C10—C9121.0 (3)
C4—C19—H19B109.5C11—C10—H10119.5
H19A—C19—H19B109.5C9—C10—H10119.5
C4—C19—H19C109.5C10—C11—C12120.0 (4)
H19A—C19—H19C109.5C10—C11—H11120
H19B—C19—H19C109.5C12—C11—H11120
C14—C13—C18119.6 (3)C7—C12—C11117.9 (3)
C14—C13—C6118.5 (3)C7—C12—H12121
C18—C13—C6121.8 (3)C11—C12—H12121
C15—C14—C13120.5 (4)C9—O1—C20116.1 (3)
C15—C14—H14119.7O1—C20—H20A109.5
C13—C14—H14119.7O1—C20—H20B109.5
C14—C15—C16119.8 (4)H20A—C20—H20B109.5
C14—C15—H15120.1O1—C20—H20C109.5
C16—C15—H15120.1H20A—C20—H20C109.5
C17—C16—C15119.8 (4)H20B—C20—H20C109.5
C17—C16—H16120.1
N1—C2—N3—C45.1 (5)C13—C14—C15—C160.0 (6)
Se1—C2—N3—C4174.8 (3)C14—C15—C16—C170.6 (6)
C2—N3—C4—C51.0 (5)C15—C16—C17—C180.9 (6)
C2—N3—C4—C19179.9 (3)C16—C17—C18—C130.7 (5)
N3—C4—C5—C62.6 (5)C14—C13—C18—C170.1 (5)
C19—C4—C5—C6176.5 (4)C6—C13—C18—C17175.2 (3)
C4—C5—C6—N11.8 (5)C6—N1—C7—C872.6 (4)
C4—C5—C6—C13177.8 (3)C2—N1—C7—C8106.7 (4)
C5—C6—N1—C22.3 (5)C6—N1—C7—C12103.6 (4)
C13—C6—N1—C2178.1 (3)C2—N1—C7—C1277.2 (4)
C5—C6—N1—C7178.4 (3)C12—C7—C8—C90.5 (5)
C13—C6—N1—C71.1 (5)N1—C7—C8—C9175.4 (3)
N3—C2—N1—C65.8 (5)C7—C8—C9—O1178.9 (3)
Se1—C2—N1—C6174.1 (2)C7—C8—C9—C100.7 (5)
N3—C2—N1—C7174.9 (3)O1—C9—C10—C11179.3 (3)
Se1—C2—N1—C75.2 (4)C8—C9—C10—C110.2 (5)
C5—C6—C13—C1461.2 (4)C9—C10—C11—C120.4 (5)
N1—C6—C13—C14119.2 (4)C8—C7—C12—C110.1 (5)
C5—C6—C13—C18114.2 (4)N1—C7—C12—C11176.0 (3)
N1—C6—C13—C1865.4 (4)C10—C11—C12—C70.5 (5)
C18—C13—C14—C150.2 (5)C10—C9—O1—C20161.7 (3)
C6—C13—C14—C15175.7 (3)C8—C9—O1—C2017.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.932.633.557 (4)175
C8—H8···N3ii0.932.723.415 (5)133
C19—H19B···Se1iii0.963.063.674 (4)123
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1, z+1; (iii) x, y+3/2, z1/2.
4-Methyl-1-(4-methoxyphenyl)-6-phenylpyrimidine-2(1H)-selenone (3) top
Crystal data top
C18H16N2OSeF(000) = 720
Mr = 355.29Dx = 1.496 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 18676 reflections
a = 12.7330 (3) Åθ = 1.0–27.5°
b = 8.9500 (2) ŵ = 2.38 mm1
c = 14.1399 (5) ÅT = 100 K
β = 101.862 (2)°Needle, orange
V = 1576.98 (7) Å30.99 × 0.43 × 0.08 mm
Z = 4
Data collection top
Bruker KappaCCD
diffractometer
3626 independent reflections
Horizonally mounted graphite crystal monochromator3229 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm-1Rint = 0.104
CCD scansθmax = 27.7°, θmin = 3.0°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1516
Tmin = 0.868, Tmax = 1.187k = 1111
17877 measured reflectionsl = 2221
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0604P)2 + 1.1117P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.94 e Å3
3626 reflectionsΔρmin = 0.82 e Å3
202 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0249 (17)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.52843 (15)0.7407 (2)0.43405 (13)0.0123 (4)
C20.46185 (19)0.6927 (2)0.49498 (17)0.0117 (4)
N30.36047 (15)0.6493 (2)0.45589 (14)0.0136 (4)
C40.32605 (18)0.6505 (2)0.36117 (17)0.0149 (4)
C50.39026 (19)0.6995 (2)0.29741 (17)0.0149 (5)
H50.3629340.7021770.2296510.018*
C60.49275 (18)0.7429 (2)0.33549 (16)0.0136 (4)
C70.63567 (19)0.7957 (2)0.47412 (16)0.0125 (4)
C80.72006 (19)0.6957 (2)0.49859 (16)0.0132 (4)
H80.7077670.591250.4910310.016*
C90.82185 (18)0.7494 (3)0.53396 (16)0.0154 (4)
H90.8803820.6819850.550340.018*
C100.83927 (18)0.9039 (2)0.54585 (16)0.0148 (4)
C110.75435 (19)1.0028 (2)0.52104 (17)0.0166 (4)
H110.7659761.1072680.529180.02*
C120.65183 (18)0.9478 (2)0.48407 (16)0.0155 (4)
H120.5932661.0147120.4657730.019*
C130.56766 (19)0.7855 (3)0.27191 (16)0.0142 (4)
C140.6437 (2)0.6833 (3)0.25498 (19)0.0202 (5)
H140.6516730.5902850.2880790.024*
C150.7082 (2)0.7171 (3)0.1895 (2)0.0233 (5)
H150.7604130.6473270.1781380.028*
C160.6964 (2)0.8524 (3)0.14084 (18)0.0227 (5)
H160.7401880.8750110.0958830.027*
C170.6205 (2)0.9548 (3)0.15775 (19)0.0237 (5)
H170.6124711.0475130.1243470.028*
C180.55606 (19)0.9218 (3)0.22372 (18)0.0190 (5)
H180.5044490.9921380.2356640.023*
C190.21606 (19)0.5904 (3)0.32206 (18)0.0204 (5)
H19A0.2211020.4845750.30570.031*
H19B0.1830760.6463210.263950.031*
H19C0.1719780.6008240.3709110.031*
C200.9634 (2)1.0987 (3)0.60663 (19)0.0243 (5)
H20A0.9437551.1584160.547550.036*
H20B1.0397851.1125860.634650.036*
H20C0.9206341.1308130.653220.036*
O10.94287 (13)0.94392 (19)0.58392 (12)0.0197 (4)
Se10.50781 (2)0.68872 (2)0.62690 (2)0.01518 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0136 (9)0.0105 (8)0.0131 (9)0.0011 (7)0.0030 (7)0.0012 (7)
C20.0151 (11)0.0084 (9)0.0124 (10)0.0022 (7)0.0046 (8)0.0013 (7)
N30.0138 (9)0.0113 (8)0.0162 (9)0.0009 (7)0.0044 (7)0.0013 (7)
C40.0139 (11)0.0123 (9)0.0182 (11)0.0018 (8)0.0026 (8)0.0010 (8)
C50.0163 (12)0.0170 (11)0.0112 (11)0.0007 (8)0.0023 (8)0.0010 (8)
C60.0179 (11)0.0104 (9)0.0130 (11)0.0030 (8)0.0043 (8)0.0019 (8)
C70.0144 (11)0.0132 (10)0.0104 (10)0.0005 (8)0.0034 (8)0.0001 (7)
C80.0165 (11)0.0109 (10)0.0126 (11)0.0018 (8)0.0041 (8)0.0002 (7)
C90.0164 (11)0.0146 (11)0.0156 (11)0.0027 (9)0.0042 (8)0.0019 (9)
C100.0151 (11)0.0177 (11)0.0117 (10)0.0018 (8)0.0033 (8)0.0005 (8)
C110.0204 (12)0.0121 (10)0.0173 (11)0.0013 (8)0.0041 (8)0.0004 (8)
C120.0165 (11)0.0130 (10)0.0175 (11)0.0024 (8)0.0046 (8)0.0009 (8)
C130.0145 (11)0.0171 (10)0.0110 (10)0.0039 (8)0.0025 (8)0.0005 (8)
C140.0240 (13)0.0209 (12)0.0173 (12)0.0040 (9)0.0078 (10)0.0040 (9)
C150.0226 (13)0.0277 (12)0.0223 (13)0.0027 (10)0.0108 (10)0.0014 (10)
C160.0225 (12)0.0299 (13)0.0178 (12)0.0072 (10)0.0089 (9)0.0010 (10)
C170.0252 (13)0.0237 (12)0.0235 (13)0.0045 (10)0.0082 (10)0.0073 (10)
C180.0178 (11)0.0194 (11)0.0203 (12)0.0004 (9)0.0053 (9)0.0036 (9)
C190.0151 (11)0.0241 (12)0.0209 (12)0.0029 (9)0.0011 (9)0.0036 (9)
C200.0220 (13)0.0259 (13)0.0241 (13)0.0077 (10)0.0027 (10)0.0066 (10)
O10.0159 (8)0.0218 (8)0.0205 (9)0.0039 (7)0.0016 (6)0.0031 (7)
Se10.01769 (17)0.01759 (16)0.01080 (16)0.00157 (8)0.00421 (10)0.00130 (7)
Geometric parameters (Å, º) top
N1—C61.374 (3)C11—H110.95
N1—C21.395 (3)C12—H120.95
N1—C71.452 (3)C13—C141.388 (3)
C2—N31.353 (3)C13—C181.390 (3)
C2—Se11.837 (2)C14—C151.391 (3)
N3—C41.321 (3)C14—H140.95
C4—C51.406 (3)C15—C161.385 (4)
C4—C191.496 (3)C15—H150.95
C5—C61.362 (3)C16—C171.387 (4)
C5—H50.95C16—H160.95
C6—C131.489 (3)C17—C181.395 (3)
C7—C121.380 (3)C17—H170.95
C7—C81.387 (3)C18—H180.95
C8—C91.377 (3)C19—H19A0.98
C8—H80.95C19—H19B0.98
C9—C101.405 (3)C19—H19C0.98
C9—H90.95C20—O11.434 (3)
C10—O11.366 (3)C20—H20A0.98
C10—C111.386 (3)C20—H20B0.98
C11—C121.393 (3)C20—H20C0.98
C6—N1—C2120.96 (19)C11—C12—H12120.1
C6—N1—C7118.63 (18)C14—C13—C18120.1 (2)
C2—N1—C7120.35 (19)C14—C13—C6119.4 (2)
N3—C2—N1119.1 (2)C18—C13—C6120.3 (2)
N3—C2—Se1119.17 (16)C13—C14—C15119.9 (2)
N1—C2—Se1121.73 (17)C13—C14—H14120
C4—N3—C2120.12 (19)C15—C14—H14120
N3—C4—C5122.5 (2)C16—C15—C14120.1 (2)
N3—C4—C19117.5 (2)C16—C15—H15119.9
C5—C4—C19119.9 (2)C14—C15—H15119.9
C6—C5—C4118.1 (2)C15—C16—C17120.0 (2)
C6—C5—H5120.9C15—C16—H16120
C4—C5—H5120.9C17—C16—H16120
C5—C6—N1119.1 (2)C16—C17—C18120.1 (2)
C5—C6—C13121.0 (2)C16—C17—H17120
N1—C6—C13119.8 (2)C18—C17—H17120
C12—C7—C8121.3 (2)C13—C18—C17119.7 (2)
C12—C7—N1118.9 (2)C13—C18—H18120.1
C8—C7—N1119.78 (19)C17—C18—H18120.1
C9—C8—C7119.2 (2)C4—C19—H19A109.5
C9—C8—H8120.4C4—C19—H19B109.5
C7—C8—H8120.4H19A—C19—H19B109.5
C8—C9—C10120.1 (2)C4—C19—H19C109.5
C8—C9—H9120H19A—C19—H19C109.5
C10—C9—H9120H19B—C19—H19C109.5
O1—C10—C11124.9 (2)O1—C20—H20A109.5
O1—C10—C9114.91 (19)O1—C20—H20B109.5
C11—C10—C9120.2 (2)H20A—C20—H20B109.5
C10—C11—C12119.5 (2)O1—C20—H20C109.5
C10—C11—H11120.3H20A—C20—H20C109.5
C12—C11—H11120.3H20B—C20—H20C109.5
C7—C12—C11119.7 (2)C10—O1—C20117.29 (18)
C7—C12—H12120.1
C6—N1—C2—N30.7 (3)C7—C8—C9—C100.6 (3)
C7—N1—C2—N3176.62 (18)C8—C9—C10—O1178.3 (2)
C6—N1—C2—Se1179.97 (15)C8—C9—C10—C110.7 (3)
C7—N1—C2—Se12.7 (3)O1—C10—C11—C12179.0 (2)
N1—C2—N3—C41.0 (3)C9—C10—C11—C120.2 (3)
Se1—C2—N3—C4179.63 (16)C8—C7—C12—C111.2 (3)
C2—N3—C4—C51.7 (3)N1—C7—C12—C11179.07 (19)
C2—N3—C4—C19175.46 (19)C10—C11—C12—C71.1 (3)
N3—C4—C5—C61.9 (3)C5—C6—C13—C14100.5 (3)
C19—C4—C5—C6175.1 (2)N1—C6—C13—C1476.6 (3)
C4—C5—C6—N11.5 (3)C5—C6—C13—C1874.3 (3)
C4—C5—C6—C13175.6 (2)N1—C6—C13—C18108.6 (3)
C2—N1—C6—C51.0 (3)C18—C13—C14—C150.2 (4)
C7—N1—C6—C5176.35 (19)C6—C13—C14—C15174.7 (2)
C2—N1—C6—C13176.16 (19)C13—C14—C15—C160.3 (4)
C7—N1—C6—C136.5 (3)C14—C15—C16—C170.4 (4)
C6—N1—C7—C1280.2 (3)C15—C16—C17—C180.0 (4)
C2—N1—C7—C1297.1 (2)C14—C13—C18—C170.5 (4)
C6—N1—C7—C897.7 (2)C6—C13—C18—C17174.3 (2)
C2—N1—C7—C885.0 (3)C16—C17—C18—C130.4 (4)
C12—C7—C8—C90.3 (3)C11—C10—O1—C205.0 (3)
N1—C7—C8—C9178.2 (2)C9—C10—O1—C20173.93 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···N3i0.952.493.357 (3)151
C11—H11···N3ii0.952.743.484 (3)135
C12—H12···Se1ii0.953.123.983 (2)152
C16—H16···N3iii0.952.753.668 (3)163
C19—H19B···Se1iv0.983.023.943 (2)157
C20—H20C···Se1v0.983.13.796 (3)129
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z+1; (iii) x+1, y+3/2, z1/2; (iv) x, y+3/2, z1/2; (v) x+1, y+1/2, z+3/2.
The comparison of selected torsion angles (°) for 1, 2, 3 and LS top
Torsion angle1 A/B23LS
C2—N1—C7—C887.1 (2)/90.2 (2)77.2 (4)85.0 (3)78.9 (2)
C2—N1—C7—C12-97.7 (2)/-90.8 (2)-106.7 (4)-97.1 (3)-102.6 (2)
C5—C6—C13—C14-120.5 (2)/-97.5 (2)-114.2 (4)-100.5 (3)-112.1 (2)
C5—C6—C13—C1860.2 (2)/82.1 (2)61.2 (5)74.3 (3)66.5 (2)
The antimicrobial activity (mg l-1) of reference compounds vancomycin and fluconazole against reference bacterial and fungal strains top
MicroorganismMICMBCMBC/MIC
Against vancomycin
S. aureus ATCC65380.491.954
S. aureus ATCC259230.987.818
S. aureus ATCC433000.491.954
S. epidermidis ATCC122280.980.981
M. luteus ATCC102400.120.121
B. subtilis ATCC66330.240.492
B. cereus ATCC108760.9815.616
S. pyogenes ATCC196150.240.492
S. pneumoniae ATCC496190.240.492
S. mutans ATCC251750.980.981
Against fluconazole
C. albicans ATCC1022310.981.952
C. albicans ATCC20910.250.251
C. parapsilosis ATCC220191.951.951
 

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