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In the title compound, C23H21N3Se, the C-bound phenyl ring is almost coplanar with the central five-membered ring [dihedral angle = 2.84 (10)°], but the N-bound benzene ring is inclined [dihedral angle = 47.52 (10)°]. The dihedral angle between the Se-bound rings is 69.24 (9)°. An intra­molecular Se...N inter­action of 3.0248 (15) Å is noted. In the crystal, C—H...π inter­actions connect mol­ecules into double layers that stack along the a axis with no directional inter­actions between them.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015003229/hg5433sup1.cif
Contains datablocks I, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015003229/hg5433Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015003229/hg5433Isup3.cml
Supplementary material

CCDC reference: 1049547

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.063
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 2 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 124 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 0 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Related literature top

For background and synthesis of arylseleno-1,2,3-triazoles, including of the title compound, see: Deobald et al. (2011). For Se···N interactions, see: Pati & Zade (2014). For a related organoselenium compound with a 1,2,3-triazole residue, see: Camargo et al. (2015).

Experimental top

The compound was prepared in accord with the literature (Deobald et al., 2011). Crystals were obtained by taking 200 mg of sample into a sample vial containing methanol (5 ml) and ethyl acetate (5 ml) and letting it stand at room temperature.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
[Figure 2] Fig. 2. A view in projection down the b axis of the unit-cell contents. The C—H···π interactions are shown as purple dashed lines.
4-Phenyl-1-{2-[(2,4,6-trimethylphenyl)selanyl]phenyl}-1H-1,2,3-triazole top
Crystal data top
C23H21N3SeF(000) = 856
Mr = 418.39Dx = 1.451 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 21.3924 (4) ÅCell parameters from 4584 reflections
b = 6.9332 (1) Åθ = 2.4–29.3°
c = 12.9204 (2) ŵ = 1.97 mm1
β = 92.231 (2)°T = 100 K
V = 1914.87 (5) Å3Prism, colourless
Z = 40.20 × 0.15 × 0.10 mm
Data collection top
Agilent SuperNova CCD
diffractometer
3740 reflections with I > 2σ(I)
Radiation source: SuperNova (Cu) X-ray SourceRint = 0.026
ω scansθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
h = 2527
Tmin = 0.809, Tmax = 1.000k = 87
9275 measured reflectionsl = 1612
4252 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.063 w = 1/[σ2(Fo2) + (0.0204P)2 + 1.1744P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4252 reflectionsΔρmax = 0.38 e Å3
247 parametersΔρmin = 0.39 e Å3
Crystal data top
C23H21N3SeV = 1914.87 (5) Å3
Mr = 418.39Z = 4
Monoclinic, P21/cMo Kα radiation
a = 21.3924 (4) ŵ = 1.97 mm1
b = 6.9332 (1) ÅT = 100 K
c = 12.9204 (2) Å0.20 × 0.15 × 0.10 mm
β = 92.231 (2)°
Data collection top
Agilent SuperNova CCD
diffractometer
4252 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
3740 reflections with I > 2σ(I)
Tmin = 0.809, Tmax = 1.000Rint = 0.026
9275 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.063H-atom parameters constrained
S = 1.03Δρmax = 0.38 e Å3
4252 reflectionsΔρmin = 0.39 e Å3
247 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se0.76393 (2)0.40426 (3)0.12277 (2)0.01683 (7)
N10.65328 (7)0.6076 (2)0.23160 (12)0.0130 (3)
N20.65949 (7)0.6956 (2)0.13866 (12)0.0175 (4)
N30.60302 (7)0.7185 (2)0.09728 (12)0.0171 (3)
C10.83935 (8)0.2521 (3)0.13795 (14)0.0132 (4)
C20.84041 (9)0.0834 (3)0.19790 (14)0.0143 (4)
C30.89540 (9)0.0249 (3)0.20417 (15)0.0168 (4)
H30.89660.13930.24470.020*
C40.94859 (9)0.0300 (3)0.15272 (15)0.0181 (4)
C50.94552 (9)0.1966 (3)0.09317 (15)0.0182 (4)
H50.98140.23470.05710.022*
C60.89188 (9)0.3100 (3)0.08433 (14)0.0157 (4)
C70.78440 (9)0.0169 (3)0.25528 (16)0.0192 (4)
H7A0.79440.10430.29120.029*
H7B0.74900.00330.20600.029*
H7C0.77340.11520.30600.029*
C81.00802 (10)0.0852 (4)0.16441 (17)0.0291 (5)
H8A0.99840.22280.15700.044*
H8B1.02770.06150.23300.044*
H8C1.03670.04640.11090.044*
C90.89247 (10)0.4894 (3)0.01805 (17)0.0250 (5)
H9A0.88300.60210.06050.038*
H9B0.86090.47750.03860.038*
H9C0.93390.50500.01070.038*
C100.76174 (8)0.4997 (3)0.26208 (14)0.0130 (4)
C110.81423 (9)0.4896 (3)0.32961 (14)0.0146 (4)
H110.85240.44010.30550.017*
C120.81130 (9)0.5511 (3)0.43132 (15)0.0153 (4)
H120.84730.54210.47640.018*
C130.75617 (9)0.6257 (3)0.46787 (15)0.0163 (4)
H130.75410.66520.53810.020*
C140.70405 (9)0.6421 (3)0.40097 (15)0.0160 (4)
H140.66630.69540.42480.019*
C150.70724 (8)0.5805 (3)0.29941 (14)0.0123 (4)
C160.59254 (8)0.5762 (3)0.24976 (15)0.0145 (4)
H160.57560.51840.30910.017*
C170.56039 (8)0.6464 (3)0.16345 (15)0.0135 (4)
C180.49267 (9)0.6540 (3)0.13925 (15)0.0151 (4)
C190.46969 (9)0.7268 (3)0.04465 (15)0.0198 (4)
H190.49800.77220.00470.024*
C200.40557 (9)0.7336 (3)0.02211 (16)0.0240 (5)
H200.39020.78460.04220.029*
C210.36407 (9)0.6660 (3)0.09340 (17)0.0221 (5)
H210.32030.66880.07750.026*
C220.38639 (9)0.5945 (3)0.18778 (17)0.0223 (4)
H220.35790.54930.23690.027*
C230.45047 (9)0.5887 (3)0.21079 (16)0.0186 (4)
H230.46550.53990.27580.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se0.01516 (10)0.02217 (11)0.01296 (10)0.00690 (8)0.00215 (7)0.00303 (8)
N10.0107 (7)0.0140 (8)0.0142 (8)0.0002 (6)0.0017 (6)0.0018 (7)
N20.0137 (8)0.0231 (9)0.0157 (8)0.0002 (7)0.0015 (6)0.0047 (7)
N30.0119 (8)0.0213 (9)0.0182 (8)0.0012 (7)0.0001 (6)0.0031 (7)
C10.0109 (9)0.0163 (9)0.0121 (9)0.0018 (7)0.0019 (7)0.0050 (8)
C20.0144 (9)0.0154 (9)0.0131 (9)0.0029 (8)0.0009 (7)0.0050 (8)
C30.0212 (10)0.0146 (9)0.0145 (9)0.0024 (8)0.0002 (8)0.0005 (8)
C40.0155 (10)0.0244 (11)0.0141 (9)0.0035 (8)0.0022 (7)0.0044 (8)
C50.0133 (9)0.0272 (11)0.0142 (9)0.0034 (8)0.0013 (7)0.0026 (9)
C60.0168 (9)0.0168 (10)0.0134 (9)0.0023 (8)0.0002 (7)0.0020 (8)
C70.0183 (10)0.0189 (10)0.0208 (10)0.0021 (8)0.0042 (8)0.0006 (9)
C80.0208 (11)0.0446 (14)0.0218 (11)0.0143 (10)0.0007 (9)0.0016 (11)
C90.0254 (11)0.0257 (11)0.0241 (11)0.0018 (9)0.0027 (9)0.0078 (10)
C100.0162 (9)0.0105 (9)0.0124 (9)0.0008 (7)0.0006 (7)0.0003 (8)
C110.0122 (9)0.0147 (9)0.0167 (9)0.0008 (7)0.0006 (7)0.0013 (8)
C120.0164 (9)0.0138 (9)0.0154 (9)0.0005 (8)0.0034 (7)0.0011 (8)
C130.0199 (10)0.0167 (10)0.0125 (9)0.0016 (8)0.0021 (7)0.0013 (8)
C140.0134 (9)0.0154 (9)0.0196 (10)0.0012 (7)0.0052 (8)0.0007 (8)
C150.0109 (9)0.0096 (9)0.0165 (9)0.0020 (7)0.0005 (7)0.0032 (8)
C160.0111 (9)0.0124 (9)0.0201 (10)0.0004 (7)0.0033 (7)0.0009 (8)
C170.0122 (9)0.0107 (9)0.0178 (9)0.0007 (7)0.0015 (7)0.0014 (8)
C180.0137 (9)0.0116 (9)0.0199 (10)0.0010 (7)0.0005 (8)0.0027 (8)
C190.0174 (10)0.0259 (11)0.0162 (10)0.0017 (8)0.0016 (8)0.0032 (9)
C200.0196 (10)0.0305 (12)0.0215 (10)0.0059 (9)0.0055 (8)0.0053 (10)
C210.0124 (9)0.0234 (11)0.0300 (12)0.0015 (8)0.0042 (8)0.0089 (10)
C220.0145 (10)0.0182 (10)0.0344 (12)0.0018 (8)0.0030 (9)0.0016 (10)
C230.0151 (9)0.0160 (10)0.0245 (10)0.0005 (8)0.0004 (8)0.0048 (9)
Geometric parameters (Å, º) top
Se—C101.9199 (18)C9—H9C0.9800
Se—C11.9311 (18)C10—C151.396 (3)
N1—C161.347 (2)C10—C111.397 (2)
N1—N21.358 (2)C11—C121.385 (3)
N1—C151.434 (2)C11—H110.9500
N2—N31.311 (2)C12—C131.387 (3)
N3—C171.369 (2)C12—H120.9500
C1—C61.402 (3)C13—C141.389 (3)
C1—C21.403 (3)C13—H130.9500
C2—C31.395 (3)C14—C151.384 (3)
C2—C71.506 (3)C14—H140.9500
C3—C41.393 (3)C16—C171.376 (3)
C3—H30.9500C16—H160.9500
C4—C51.388 (3)C17—C181.471 (3)
C4—C81.504 (3)C18—C231.393 (3)
C5—C61.392 (3)C18—C191.394 (3)
C5—H50.9500C19—C201.392 (3)
C6—C91.510 (3)C19—H190.9500
C7—H7A0.9800C20—C211.385 (3)
C7—H7B0.9800C20—H200.9500
C7—H7C0.9800C21—C221.384 (3)
C8—H8A0.9800C21—H210.9500
C8—H8B0.9800C22—C231.392 (3)
C8—H8C0.9800C22—H220.9500
C9—H9A0.9800C23—H230.9500
C9—H9B0.9800
C10—Se—C198.26 (8)C15—C10—C11117.77 (17)
C16—N1—N2110.77 (15)C15—C10—Se120.88 (13)
C16—N1—C15129.16 (16)C11—C10—Se121.34 (14)
N2—N1—C15119.66 (14)C12—C11—C10120.82 (17)
N3—N2—N1107.14 (14)C12—C11—H11119.6
N2—N3—C17109.07 (15)C10—C11—H11119.6
C6—C1—C2121.05 (16)C11—C12—C13120.54 (17)
C6—C1—Se118.43 (14)C11—C12—H12119.7
C2—C1—Se120.48 (14)C13—C12—H12119.7
C3—C2—C1118.44 (17)C12—C13—C14119.42 (18)
C3—C2—C7119.49 (17)C12—C13—H13120.3
C1—C2—C7122.06 (17)C14—C13—H13120.3
C4—C3—C2121.86 (18)C15—C14—C13119.79 (17)
C4—C3—H3119.1C15—C14—H14120.1
C2—C3—H3119.1C13—C14—H14120.1
C5—C4—C3118.04 (17)C14—C15—C10121.60 (17)
C5—C4—C8121.29 (19)C14—C15—N1118.08 (16)
C3—C4—C8120.65 (19)C10—C15—N1120.30 (16)
C4—C5—C6122.45 (18)N1—C16—C17104.89 (16)
C4—C5—H5118.8N1—C16—H16127.6
C6—C5—H5118.8C17—C16—H16127.6
C5—C6—C1118.15 (18)N3—C17—C16108.13 (16)
C5—C6—C9119.12 (18)N3—C17—C18121.92 (17)
C1—C6—C9122.73 (17)C16—C17—C18129.94 (18)
C2—C7—H7A109.5C23—C18—C19118.95 (17)
C2—C7—H7B109.5C23—C18—C17120.39 (17)
H7A—C7—H7B109.5C19—C18—C17120.66 (18)
C2—C7—H7C109.5C20—C19—C18120.43 (19)
H7A—C7—H7C109.5C20—C19—H19119.8
H7B—C7—H7C109.5C18—C19—H19119.8
C4—C8—H8A109.5C21—C20—C19120.09 (19)
C4—C8—H8B109.5C21—C20—H20120.0
H8A—C8—H8B109.5C19—C20—H20120.0
C4—C8—H8C109.5C22—C21—C20119.93 (18)
H8A—C8—H8C109.5C22—C21—H21120.0
H8B—C8—H8C109.5C20—C21—H21120.0
C6—C9—H9A109.5C21—C22—C23120.1 (2)
C6—C9—H9B109.5C21—C22—H22119.9
H9A—C9—H9B109.5C23—C22—H22120.0
C6—C9—H9C109.5C22—C23—C18120.50 (19)
H9A—C9—H9C109.5C22—C23—H23119.8
H9B—C9—H9C109.5C18—C23—H23119.8
C16—N1—N2—N30.6 (2)C11—C10—C15—C142.5 (3)
C15—N1—N2—N3173.99 (15)Se—C10—C15—C14177.07 (14)
N1—N2—N3—C170.3 (2)C11—C10—C15—N1175.45 (16)
C6—C1—C2—C30.8 (3)Se—C10—C15—N14.9 (2)
Se—C1—C2—C3178.16 (13)C16—N1—C15—C1443.5 (3)
C6—C1—C2—C7179.33 (17)N2—N1—C15—C14128.46 (18)
Se—C1—C2—C72.0 (2)C16—N1—C15—C10138.4 (2)
C1—C2—C3—C40.1 (3)N2—N1—C15—C1049.6 (2)
C7—C2—C3—C4179.96 (18)N2—N1—C16—C170.7 (2)
C2—C3—C4—C50.6 (3)C15—N1—C16—C17173.24 (17)
C2—C3—C4—C8177.51 (18)N2—N3—C17—C160.1 (2)
C3—C4—C5—C60.7 (3)N2—N3—C17—C18179.00 (17)
C8—C4—C5—C6177.43 (18)N1—C16—C17—N30.5 (2)
C4—C5—C6—C10.0 (3)N1—C16—C17—C18179.26 (18)
C4—C5—C6—C9179.89 (18)N3—C17—C18—C23176.52 (18)
C2—C1—C6—C50.8 (3)C16—C17—C18—C232.1 (3)
Se—C1—C6—C5178.15 (14)N3—C17—C18—C193.3 (3)
C2—C1—C6—C9179.32 (18)C16—C17—C18—C19178.05 (19)
Se—C1—C6—C91.9 (2)C23—C18—C19—C200.2 (3)
C15—C10—C11—C122.5 (3)C17—C18—C19—C20179.96 (18)
Se—C10—C11—C12177.11 (14)C18—C19—C20—C210.6 (3)
C10—C11—C12—C130.6 (3)C19—C20—C21—C221.0 (3)
C11—C12—C13—C141.3 (3)C20—C21—C22—C230.6 (3)
C12—C13—C14—C151.3 (3)C21—C22—C23—C180.2 (3)
C13—C14—C15—C100.7 (3)C19—C18—C23—C220.6 (3)
C13—C14—C15—N1177.35 (16)C17—C18—C23—C22179.55 (18)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C10–C15 and C18–C23 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C12—H12···Cg1i0.952.683.481 (2)143
C7—H7a···Cg2ii0.982.613.492 (2)150
C16—H16···Cg3iii0.952.663.399 (2)135
Symmetry codes: (i) x, y1/2, z1/2; (ii) x, y1, z; (iii) x+1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C10–C15 and C18–C23 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C12—H12···Cg1i0.952.683.481 (2)143
C7—H7a···Cg2ii0.982.613.492 (2)150
C16—H16···Cg3iii0.952.663.399 (2)135
Symmetry codes: (i) x, y1/2, z1/2; (ii) x, y1, z; (iii) x+1, y1/2, z+1/2.
 

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