Crystal structure of 4-phenyl-1-{2-[(2,4,6-tri­methyl­phen­yl)selan­yl]phen­yl}-1H-1,2,3-triazole

Camargo, L.R.S.; Zukerman-Schpector, J.; Deobald, A.M.; Braga, A.L.; Tiekink, E.R.T.

doi:10.1107/S2056989015003229

organic compounds

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ISSN: 2056-9890

Volume 71| Part 3| March 2015| Pages o204-o205

doi:10.1107/S2056989015003229

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Crystal structure of 4-phenyl-1-{2-[(2,4,6-trimethylphenyl)selanyl]phenyl}-1H-1,2,3-triazole

Leandro R. S. Camargo,^a Julio Zukerman-Schpector,^a ^* Anna M. Deobald,^b ‡ Antonio L. Braga ^c and Edward R. T. Tiekink ^d

^aDepartmento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, ^bDepartmento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil, ^cDepartmento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis, SC, Brazil, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: julio@power.ufscar.br

Edited by P. C. Healy, Griffith University, Australia (Received 12 February 2015; accepted 16 February 2015; online 25 February 2015)

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.

Keywords: crystal structure; organoselenium; hydrogen bonding; Se⋯N halogen bonding; C—H⋯π interactions.

CCDC reference: 1049547

1. Related literature

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 ).

2. Experimental

2.1. Crystal data

C₂₃H₂₁N₃Se
M_r = 418.39
Monoclinic, P 2₁ /c
a = 21.3924 (4) Å
b = 6.9332 (1) Å
c = 12.9204 (2) Å
β = 92.231 (2)°
V = 1914.87 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.97 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.10 mm

2.2. Data collection

Agilent SuperNova CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.809, T_max = 1.000
9275 measured reflections
4252 independent reflections
3740 reflections with I > 2σ(I)
R_int = 0.026

2.3. Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.063
S = 1.03
4252 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C10–C15 and C18–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg1ⁱ	0.95	2.68	3.481 (2)	143
C7—H7a⋯Cg2ⁱⁱ	0.98	2.61	3.492 (2)	150
C16—H16⋯Cg3ⁱⁱⁱ	0.95	2.66	3.399 (2)	135
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ).

Supporting information

CCDC reference: 1049547

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015003229/hg5433sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015003229/hg5433Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015003229/hg5433Isup3.cml

checkCIF report

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.

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

	Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
	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

C₂₃H₂₁N₃Se	F(000) = 856
M_r = 418.39	D_x = 1.451 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.3924 (4) Å	Cell parameters from 4584 reflections
b = 6.9332 (1) Å	θ = 2.4–29.3°
c = 12.9204 (2) Å	µ = 1.97 mm⁻¹
β = 92.231 (2)°	T = 100 K
V = 1914.87 (5) Å³	Prism, colourless
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection top

Agilent SuperNova CCD diffractometer	3740 reflections with I > 2σ(I)
Radiation source: SuperNova (Cu) X-ray Source	R_int = 0.026
ω scans	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −25→27
T_min = 0.809, T_max = 1.000	k = −8→7
9275 measured reflections	l = −16→12
4252 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.063	w = 1/[σ²(F_o²) + (0.0204P)² + 1.1744P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4252 reflections	Δρ_max = 0.38 e Å⁻³
247 parameters	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₃H₂₁N₃Se	V = 1914.87 (5) Å³
M_r = 418.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.3924 (4) Å	µ = 1.97 mm⁻¹
b = 6.9332 (1) Å	T = 100 K
c = 12.9204 (2) Å	0.20 × 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)
T_min = 0.809, T_max = 1.000	R_int = 0.026
9275 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
4252 reflections	Δρ_min = −0.39 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Se	0.76393 (2)	0.40426 (3)	0.12277 (2)	0.01683 (7)
N1	0.65328 (7)	0.6076 (2)	0.23160 (12)	0.0130 (3)
N2	0.65949 (7)	0.6956 (2)	0.13866 (12)	0.0175 (4)
N3	0.60302 (7)	0.7185 (2)	0.09728 (12)	0.0171 (3)
C1	0.83935 (8)	0.2521 (3)	0.13795 (14)	0.0132 (4)
C2	0.84041 (9)	0.0834 (3)	0.19790 (14)	0.0143 (4)
C3	0.89540 (9)	−0.0249 (3)	0.20417 (15)	0.0168 (4)
H3	0.8966	−0.1393	0.2447	0.020*
C4	0.94859 (9)	0.0300 (3)	0.15272 (15)	0.0181 (4)
C5	0.94552 (9)	0.1966 (3)	0.09317 (15)	0.0182 (4)
H5	0.9814	0.2347	0.0571	0.022*
C6	0.89188 (9)	0.3100 (3)	0.08433 (14)	0.0157 (4)
C7	0.78440 (9)	0.0169 (3)	0.25528 (16)	0.0192 (4)
H7A	0.7944	−0.1043	0.2912	0.029*
H7B	0.7490	−0.0033	0.2060	0.029*
H7C	0.7734	0.1152	0.3060	0.029*
C8	1.00802 (10)	−0.0852 (4)	0.16441 (17)	0.0291 (5)
H8A	0.9984	−0.2228	0.1570	0.044*
H8B	1.0277	−0.0615	0.2330	0.044*
H8C	1.0367	−0.0464	0.1109	0.044*
C9	0.89247 (10)	0.4894 (3)	0.01805 (17)	0.0250 (5)
H9A	0.8830	0.6021	0.0605	0.038*
H9B	0.8609	0.4775	−0.0386	0.038*
H9C	0.9339	0.5050	−0.0107	0.038*
C10	0.76174 (8)	0.4997 (3)	0.26208 (14)	0.0130 (4)
C11	0.81423 (9)	0.4896 (3)	0.32961 (14)	0.0146 (4)
H11	0.8524	0.4401	0.3055	0.017*
C12	0.81130 (9)	0.5511 (3)	0.43132 (15)	0.0153 (4)
H12	0.8473	0.5421	0.4764	0.018*
C13	0.75617 (9)	0.6257 (3)	0.46787 (15)	0.0163 (4)
H13	0.7541	0.6652	0.5381	0.020*
C14	0.70405 (9)	0.6421 (3)	0.40097 (15)	0.0160 (4)
H14	0.6663	0.6954	0.4248	0.019*
C15	0.70724 (8)	0.5805 (3)	0.29941 (14)	0.0123 (4)
C16	0.59254 (8)	0.5762 (3)	0.24976 (15)	0.0145 (4)
H16	0.5756	0.5184	0.3091	0.017*
C17	0.56039 (8)	0.6464 (3)	0.16345 (15)	0.0135 (4)
C18	0.49267 (9)	0.6540 (3)	0.13925 (15)	0.0151 (4)
C19	0.46969 (9)	0.7268 (3)	0.04465 (15)	0.0198 (4)
H19	0.4980	0.7722	−0.0047	0.024*
C20	0.40557 (9)	0.7336 (3)	0.02211 (16)	0.0240 (5)
H20	0.3902	0.7846	−0.0422	0.029*
C21	0.36407 (9)	0.6660 (3)	0.09340 (17)	0.0221 (5)
H21	0.3203	0.6688	0.0775	0.026*
C22	0.38639 (9)	0.5945 (3)	0.18778 (17)	0.0223 (4)
H22	0.3579	0.5493	0.2369	0.027*
C23	0.45047 (9)	0.5887 (3)	0.21079 (16)	0.0186 (4)
H23	0.4655	0.5399	0.2758	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se	0.01516 (10)	0.02217 (11)	0.01296 (10)	0.00690 (8)	−0.00215 (7)	−0.00303 (8)
N1	0.0107 (7)	0.0140 (8)	0.0142 (8)	0.0002 (6)	0.0017 (6)	0.0018 (7)
N2	0.0137 (8)	0.0231 (9)	0.0157 (8)	0.0002 (7)	0.0015 (6)	0.0047 (7)
N3	0.0119 (8)	0.0213 (9)	0.0182 (8)	0.0012 (7)	0.0001 (6)	0.0031 (7)
C1	0.0109 (9)	0.0163 (9)	0.0121 (9)	0.0018 (7)	−0.0019 (7)	−0.0050 (8)
C2	0.0144 (9)	0.0154 (9)	0.0131 (9)	−0.0029 (8)	0.0009 (7)	−0.0050 (8)
C3	0.0212 (10)	0.0146 (9)	0.0145 (9)	0.0024 (8)	−0.0002 (8)	−0.0005 (8)
C4	0.0155 (10)	0.0244 (11)	0.0141 (9)	0.0035 (8)	−0.0022 (7)	−0.0044 (8)
C5	0.0133 (9)	0.0272 (11)	0.0142 (9)	−0.0034 (8)	0.0013 (7)	−0.0026 (9)
C6	0.0168 (9)	0.0168 (10)	0.0134 (9)	−0.0023 (8)	−0.0002 (7)	−0.0020 (8)
C7	0.0183 (10)	0.0189 (10)	0.0208 (10)	−0.0021 (8)	0.0042 (8)	0.0006 (9)
C8	0.0208 (11)	0.0446 (14)	0.0218 (11)	0.0143 (10)	0.0007 (9)	0.0016 (11)
C9	0.0254 (11)	0.0257 (11)	0.0241 (11)	−0.0018 (9)	0.0027 (9)	0.0078 (10)
C10	0.0162 (9)	0.0105 (9)	0.0124 (9)	−0.0008 (7)	0.0006 (7)	0.0003 (8)
C11	0.0122 (9)	0.0147 (9)	0.0167 (9)	0.0008 (7)	0.0006 (7)	−0.0013 (8)
C12	0.0164 (9)	0.0138 (9)	0.0154 (9)	−0.0005 (8)	−0.0034 (7)	0.0011 (8)
C13	0.0199 (10)	0.0167 (10)	0.0125 (9)	−0.0016 (8)	0.0021 (7)	−0.0013 (8)
C14	0.0134 (9)	0.0154 (9)	0.0196 (10)	0.0012 (7)	0.0052 (8)	−0.0007 (8)
C15	0.0109 (9)	0.0096 (9)	0.0165 (9)	−0.0020 (7)	0.0005 (7)	0.0032 (8)
C16	0.0111 (9)	0.0124 (9)	0.0201 (10)	0.0004 (7)	0.0033 (7)	0.0009 (8)
C17	0.0122 (9)	0.0107 (9)	0.0178 (9)	0.0007 (7)	0.0015 (7)	−0.0014 (8)
C18	0.0137 (9)	0.0116 (9)	0.0199 (10)	0.0010 (7)	0.0005 (8)	−0.0027 (8)
C19	0.0174 (10)	0.0259 (11)	0.0162 (10)	0.0017 (8)	0.0016 (8)	−0.0032 (9)
C20	0.0196 (10)	0.0305 (12)	0.0215 (10)	0.0059 (9)	−0.0055 (8)	−0.0053 (10)
C21	0.0124 (9)	0.0234 (11)	0.0300 (12)	0.0015 (8)	−0.0042 (8)	−0.0089 (10)
C22	0.0145 (10)	0.0182 (10)	0.0344 (12)	−0.0018 (8)	0.0030 (9)	0.0016 (10)
C23	0.0151 (9)	0.0160 (10)	0.0245 (10)	0.0005 (8)	−0.0004 (8)	0.0048 (9)

Geometric parameters (Å, º) top

Se—C10	1.9199 (18)	C9—H9C	0.9800
Se—C1	1.9311 (18)	C10—C15	1.396 (3)
N1—C16	1.347 (2)	C10—C11	1.397 (2)
N1—N2	1.358 (2)	C11—C12	1.385 (3)
N1—C15	1.434 (2)	C11—H11	0.9500
N2—N3	1.311 (2)	C12—C13	1.387 (3)
N3—C17	1.369 (2)	C12—H12	0.9500
C1—C6	1.402 (3)	C13—C14	1.389 (3)
C1—C2	1.403 (3)	C13—H13	0.9500
C2—C3	1.395 (3)	C14—C15	1.384 (3)
C2—C7	1.506 (3)	C14—H14	0.9500
C3—C4	1.393 (3)	C16—C17	1.376 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.388 (3)	C17—C18	1.471 (3)
C4—C8	1.504 (3)	C18—C23	1.393 (3)
C5—C6	1.392 (3)	C18—C19	1.394 (3)
C5—H5	0.9500	C19—C20	1.392 (3)
C6—C9	1.510 (3)	C19—H19	0.9500
C7—H7A	0.9800	C20—C21	1.385 (3)
C7—H7B	0.9800	C20—H20	0.9500
C7—H7C	0.9800	C21—C22	1.384 (3)
C8—H8A	0.9800	C21—H21	0.9500
C8—H8B	0.9800	C22—C23	1.392 (3)
C8—H8C	0.9800	C22—H22	0.9500
C9—H9A	0.9800	C23—H23	0.9500
C9—H9B	0.9800

C10—Se—C1	98.26 (8)	C15—C10—C11	117.77 (17)
C16—N1—N2	110.77 (15)	C15—C10—Se	120.88 (13)
C16—N1—C15	129.16 (16)	C11—C10—Se	121.34 (14)
N2—N1—C15	119.66 (14)	C12—C11—C10	120.82 (17)
N3—N2—N1	107.14 (14)	C12—C11—H11	119.6
N2—N3—C17	109.07 (15)	C10—C11—H11	119.6
C6—C1—C2	121.05 (16)	C11—C12—C13	120.54 (17)
C6—C1—Se	118.43 (14)	C11—C12—H12	119.7
C2—C1—Se	120.48 (14)	C13—C12—H12	119.7
C3—C2—C1	118.44 (17)	C12—C13—C14	119.42 (18)
C3—C2—C7	119.49 (17)	C12—C13—H13	120.3
C1—C2—C7	122.06 (17)	C14—C13—H13	120.3
C4—C3—C2	121.86 (18)	C15—C14—C13	119.79 (17)
C4—C3—H3	119.1	C15—C14—H14	120.1
C2—C3—H3	119.1	C13—C14—H14	120.1
C5—C4—C3	118.04 (17)	C14—C15—C10	121.60 (17)
C5—C4—C8	121.29 (19)	C14—C15—N1	118.08 (16)
C3—C4—C8	120.65 (19)	C10—C15—N1	120.30 (16)
C4—C5—C6	122.45 (18)	N1—C16—C17	104.89 (16)
C4—C5—H5	118.8	N1—C16—H16	127.6
C6—C5—H5	118.8	C17—C16—H16	127.6
C5—C6—C1	118.15 (18)	N3—C17—C16	108.13 (16)
C5—C6—C9	119.12 (18)	N3—C17—C18	121.92 (17)
C1—C6—C9	122.73 (17)	C16—C17—C18	129.94 (18)
C2—C7—H7A	109.5	C23—C18—C19	118.95 (17)
C2—C7—H7B	109.5	C23—C18—C17	120.39 (17)
H7A—C7—H7B	109.5	C19—C18—C17	120.66 (18)
C2—C7—H7C	109.5	C20—C19—C18	120.43 (19)
H7A—C7—H7C	109.5	C20—C19—H19	119.8
H7B—C7—H7C	109.5	C18—C19—H19	119.8
C4—C8—H8A	109.5	C21—C20—C19	120.09 (19)
C4—C8—H8B	109.5	C21—C20—H20	120.0
H8A—C8—H8B	109.5	C19—C20—H20	120.0
C4—C8—H8C	109.5	C22—C21—C20	119.93 (18)
H8A—C8—H8C	109.5	C22—C21—H21	120.0
H8B—C8—H8C	109.5	C20—C21—H21	120.0
C6—C9—H9A	109.5	C21—C22—C23	120.1 (2)
C6—C9—H9B	109.5	C21—C22—H22	119.9
H9A—C9—H9B	109.5	C23—C22—H22	120.0
C6—C9—H9C	109.5	C22—C23—C18	120.50 (19)
H9A—C9—H9C	109.5	C22—C23—H23	119.8
H9B—C9—H9C	109.5	C18—C23—H23	119.8

C16—N1—N2—N3	−0.6 (2)	C11—C10—C15—C14	−2.5 (3)
C15—N1—N2—N3	−173.99 (15)	Se—C10—C15—C14	177.07 (14)
N1—N2—N3—C17	0.3 (2)	C11—C10—C15—N1	175.45 (16)
C6—C1—C2—C3	0.8 (3)	Se—C10—C15—N1	−4.9 (2)
Se—C1—C2—C3	178.16 (13)	C16—N1—C15—C14	−43.5 (3)
C6—C1—C2—C7	−179.33 (17)	N2—N1—C15—C14	128.46 (18)
Se—C1—C2—C7	−2.0 (2)	C16—N1—C15—C10	138.4 (2)
C1—C2—C3—C4	−0.1 (3)	N2—N1—C15—C10	−49.6 (2)
C7—C2—C3—C4	−179.96 (18)	N2—N1—C16—C17	0.7 (2)
C2—C3—C4—C5	−0.6 (3)	C15—N1—C16—C17	173.24 (17)
C2—C3—C4—C8	177.51 (18)	N2—N3—C17—C16	0.1 (2)
C3—C4—C5—C6	0.7 (3)	N2—N3—C17—C18	179.00 (17)
C8—C4—C5—C6	−177.43 (18)	N1—C16—C17—N3	−0.5 (2)
C4—C5—C6—C1	0.0 (3)	N1—C16—C17—C18	−179.26 (18)
C4—C5—C6—C9	179.89 (18)	N3—C17—C18—C23	−176.52 (18)
C2—C1—C6—C5	−0.8 (3)	C16—C17—C18—C23	2.1 (3)
Se—C1—C6—C5	−178.15 (14)	N3—C17—C18—C19	3.3 (3)
C2—C1—C6—C9	179.32 (18)	C16—C17—C18—C19	−178.05 (19)
Se—C1—C6—C9	1.9 (2)	C23—C18—C19—C20	−0.2 (3)
C15—C10—C11—C12	2.5 (3)	C17—C18—C19—C20	179.96 (18)
Se—C10—C11—C12	−177.11 (14)	C18—C19—C20—C21	−0.6 (3)
C10—C11—C12—C13	−0.6 (3)	C19—C20—C21—C22	1.0 (3)
C11—C12—C13—C14	−1.3 (3)	C20—C21—C22—C23	−0.6 (3)
C12—C13—C14—C15	1.3 (3)	C21—C22—C23—C18	−0.2 (3)
C13—C14—C15—C10	0.7 (3)	C19—C18—C23—C22	0.6 (3)
C13—C14—C15—N1	−177.35 (16)	C17—C18—C23—C22	−179.55 (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···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1ⁱ	0.95	2.68	3.481 (2)	143
C7—H7a···Cg2ⁱⁱ	0.98	2.61	3.492 (2)	150
C16—H16···Cg3ⁱⁱⁱ	0.95	2.66	3.399 (2)	135

Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, y−1, z; (iii) −x+1, y−1/2, −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···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1ⁱ	0.95	2.68	3.481 (2)	143
C7—H7a···Cg2ⁱⁱ	0.98	2.61	3.492 (2)	150
C16—H16···Cg3ⁱⁱⁱ	0.95	2.66	3.399 (2)	135

Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, y−1, z; (iii) −x+1, y−1/2, −z+1/2.

Footnotes

‡Present address: Instituto Federal de Educação, Ciência e Tecnologia Farroupilha Rua Erechim, 860 - Bairro Planalto, 98280-000 Panambi, RS, Brazil.

Acknowledgements

The Brazilian agencies CNPq (305626/2013–2 to JZ-S), CAPES, FAPESC and FAPESP (2010/10855-5 to LRSC) are acknowledged for financial support.

References

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Volume 71| Part 3| March 2015| Pages o204-o205

doi:10.1107/S2056989015003229

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 4-phenyl-1-{2-[(2,4,6-tri­methyl­phen­yl)selan­yl]phen­yl}-1H-1,2,3-triazole

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Crystal structure of 4-phenyl-1-{2-[(2,4,6-trimethylphenyl)selanyl]phenyl}-1H-1,2,3-triazole