Crystal structure of 1-{2-[(2-meth-oxy-phen-yl)selan-yl]phen-yl}-4-phenyl-1H-1,2,3-triazole.

In the title compound, C21H17N3OSe, the dihedral angles between the central five-membered ring and the C- and N-bound rings are 17.89 (10) and 42.35 (10)°, respectively, indicating the mol-ecule is twisted. The dihedral angle between the Se-bound rings is 85.36 (10)°. A close intra-molecular Se⋯O contact of 2.8507 (13) Å is noted. In the crystal, C-H⋯O, C-H⋯N and C-H⋯π inter-actions lead to the formation of supra-molecular layers parallel to (011); these stack with no specific inter-molecular inter-actions between them.

Related literature

For background to aryl­seleno-n class="Chemical">1,2,3-triazoles and to the synthesis of the title compound, see: Deobald et al. (2011 ▸). For an analysis of intra- and inter­molecular Se⋯O inter­actions, see: Linden et al. (2014 ▸). For a related organoselenium compound with a 1,2,3-triazole residue, see: Camargo et al. (2015 ▸).

Experimental

Crystal data

C21H17N3OSe

M = 406.33

Triclinic,

a = 5.6565 (3) Å

b = 10.3682 (5) Å

c = 15.3358 (7) Å

α = 81.604 (4)°

β = 80.006 (4)°

γ = 85.340 (4)°

V = 874.83 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.16 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▸) T min = 0.759, T max = 1.000

6845 measured reflections

3869 independent reflections

3548 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.064

S = 1.01

3869 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.52 e Å−3

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) un class="Chemical">sed 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 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015003230/hg5432sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015003230/hg5432Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015003230/hg5432Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015003230/hg5432fig1.tif

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

Click here for additional data file.

a . DOI: 10.1107/S2056989015003230/hg5432fig2.tif

A view in projection down the a axis of the unit-cell contents. The C—H⋯O, C—H⋯N and C—H⋯π inter­actions are shown as orange, blue and purple dashed lines, respectively.

CCDC reference: 1049507

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H17N3OSe	Z = 2
Mr = 406.33	F(000) = 412
Triclinic, P1	Dx = 1.543 Mg m−3
a = 5.6565 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3682 (5) Å	Cell parameters from 4524 reflections
c = 15.3358 (7) Å	θ = 2.6–29.2°
α = 81.604 (4)°	µ = 2.16 mm−1
β = 80.006 (4)°	T = 100 K
γ = 85.340 (4)°	Prism, colourless
V = 874.83 (8) Å3	0.30 × 0.20 × 0.10 mm

Agilent SuperNova CCD diffractometer	3548 reflections with I > 2σ(I)
Radiation source: SuperNova (Cu) X-ray Source	Rint = 0.040
ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −6→7
Tmin = 0.759, Tmax = 1.000	k = −13→12
6845 measured reflections	l = −19→19
3869 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H-atom parameters constrained
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.026P)2 + 0.4456P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.002
3869 reflections	Δρmax = 0.41 e Å−3
236 parameters	Δρmin = −0.52 e Å−3

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.

	x	y	z	Uiso*/Ueq
Se	0.46182 (3)	0.71551 (2)	0.79326 (2)	0.01503 (7)
O1	0.5130 (2)	0.51326 (12)	0.68268 (9)	0.0185 (3)
N1	0.8216 (3)	0.94528 (14)	0.79605 (10)	0.0128 (3)
N2	1.0599 (3)	0.96928 (15)	0.78243 (11)	0.0154 (3)
N3	1.1085 (3)	1.03509 (15)	0.70214 (10)	0.0150 (3)
C1	0.4930 (4)	0.4251 (2)	0.62080 (14)	0.0255 (5)
H1A	0.3570	0.4549	0.5897	0.038*
H1B	0.4669	0.3374	0.6533	0.038*
H1C	0.6414	0.4227	0.5771	0.038*
C2	0.6840 (3)	0.48102 (18)	0.73647 (12)	0.0164 (4)
C3	0.8446 (4)	0.37256 (18)	0.73332 (13)	0.0209 (4)
H3	0.8404	0.3139	0.6916	0.025*
C4	1.0113 (4)	0.34994 (19)	0.79132 (14)	0.0238 (4)
H4	1.1196	0.2750	0.7897	0.029*
C5	1.0204 (4)	0.4358 (2)	0.85130 (14)	0.0227 (4)
H5	1.1355	0.4202	0.8905	0.027*
C6	0.8611 (3)	0.54507 (19)	0.85434 (13)	0.0194 (4)
H6	0.8684	0.6041	0.8956	0.023*
C7	0.6917 (3)	0.56852 (17)	0.79755 (12)	0.0150 (4)
C8	0.5446 (3)	0.78849 (18)	0.89132 (12)	0.0153 (4)
C9	0.4431 (4)	0.73766 (19)	0.97760 (13)	0.0194 (4)
H9	0.3236	0.6758	0.9856	0.023*
C10	0.5126 (4)	0.7755 (2)	1.05209 (13)	0.0223 (4)
H10	0.4427	0.7386	1.1104	0.027*
C11	0.6845 (4)	0.8671 (2)	1.04128 (13)	0.0224 (4)
H11	0.7347	0.8922	1.0920	0.027*
C12	0.7825 (4)	0.92197 (19)	0.95603 (13)	0.0182 (4)
H12	0.8974	0.9863	0.9485	0.022*
C13	0.7135 (3)	0.88317 (17)	0.88174 (12)	0.0133 (4)
C14	0.7201 (3)	0.99764 (17)	0.72442 (12)	0.0127 (3)
H14	0.5569	0.9958	0.7172	0.015*
C15	0.9046 (3)	1.05438 (17)	0.66405 (12)	0.0124 (3)
C16	0.8998 (3)	1.12626 (17)	0.57456 (12)	0.0126 (4)
C17	1.0842 (3)	1.20866 (18)	0.53447 (13)	0.0166 (4)
H17	1.2131	1.2173	0.5651	0.020*
C18	1.0791 (3)	1.27779 (19)	0.44998 (13)	0.0192 (4)
H18	1.2047	1.3334	0.4233	0.023*
C19	0.8925 (3)	1.26635 (19)	0.40436 (13)	0.0184 (4)
H19	0.8903	1.3136	0.3465	0.022*
C20	0.7089 (3)	1.18527 (18)	0.44379 (13)	0.0180 (4)
H20	0.5802	1.1772	0.4129	0.022*
C21	0.7127 (3)	1.11581 (18)	0.52828 (12)	0.0152 (4)
H21	0.5861	1.0606	0.5547	0.018*

	U11	U22	U33	U12	U13	U23
Se	0.01551 (10)	0.01235 (10)	0.01832 (11)	−0.00120 (7)	−0.00576 (7)	−0.00192 (7)
O1	0.0237 (7)	0.0152 (7)	0.0177 (7)	−0.0024 (5)	−0.0049 (6)	−0.0032 (5)
N1	0.0117 (7)	0.0131 (7)	0.0145 (8)	−0.0021 (6)	−0.0051 (6)	−0.0002 (6)
N2	0.0108 (7)	0.0180 (8)	0.0185 (8)	−0.0012 (6)	−0.0056 (6)	−0.0015 (6)
N3	0.0125 (7)	0.0174 (8)	0.0155 (8)	−0.0012 (6)	−0.0040 (6)	−0.0011 (6)
C1	0.0338 (12)	0.0244 (11)	0.0210 (10)	−0.0045 (9)	−0.0057 (9)	−0.0090 (8)
C2	0.0193 (9)	0.0138 (9)	0.0147 (9)	−0.0045 (7)	0.0008 (8)	0.0010 (7)
C3	0.0252 (10)	0.0148 (9)	0.0200 (10)	−0.0012 (8)	0.0030 (8)	−0.0017 (8)
C4	0.0218 (10)	0.0165 (10)	0.0282 (11)	0.0032 (8)	0.0033 (9)	0.0028 (8)
C5	0.0182 (10)	0.0219 (10)	0.0265 (11)	0.0008 (8)	−0.0053 (9)	0.0021 (8)
C6	0.0182 (9)	0.0181 (9)	0.0218 (10)	−0.0020 (7)	−0.0031 (8)	−0.0024 (8)
C7	0.0148 (9)	0.0112 (8)	0.0168 (9)	−0.0014 (7)	0.0006 (7)	0.0014 (7)
C8	0.0142 (9)	0.0152 (9)	0.0168 (9)	0.0021 (7)	−0.0053 (7)	−0.0016 (7)
C9	0.0177 (9)	0.0185 (10)	0.0200 (10)	−0.0012 (7)	−0.0018 (8)	0.0020 (8)
C10	0.0228 (10)	0.0273 (11)	0.0139 (9)	0.0043 (8)	−0.0026 (8)	0.0031 (8)
C11	0.0243 (10)	0.0285 (11)	0.0154 (10)	0.0017 (8)	−0.0081 (8)	−0.0020 (8)
C12	0.0178 (9)	0.0205 (10)	0.0179 (10)	−0.0017 (7)	−0.0074 (8)	−0.0017 (8)
C13	0.0129 (8)	0.0135 (8)	0.0126 (9)	0.0018 (7)	−0.0029 (7)	0.0006 (7)
C14	0.0129 (8)	0.0135 (8)	0.0129 (9)	−0.0002 (7)	−0.0056 (7)	−0.0021 (7)
C15	0.0110 (8)	0.0123 (8)	0.0148 (9)	−0.0003 (6)	−0.0031 (7)	−0.0043 (7)
C16	0.0122 (8)	0.0121 (8)	0.0127 (9)	0.0015 (7)	−0.0007 (7)	−0.0022 (7)
C17	0.0139 (9)	0.0183 (9)	0.0183 (10)	−0.0031 (7)	−0.0036 (8)	−0.0022 (7)
C18	0.0178 (9)	0.0187 (9)	0.0191 (10)	−0.0047 (7)	0.0002 (8)	0.0018 (8)
C19	0.0199 (10)	0.0193 (9)	0.0136 (9)	0.0020 (8)	0.0000 (8)	0.0012 (7)
C20	0.0168 (9)	0.0208 (10)	0.0174 (10)	−0.0006 (8)	−0.0060 (8)	−0.0021 (8)
C21	0.0134 (9)	0.0160 (9)	0.0163 (9)	−0.0032 (7)	−0.0023 (7)	−0.0018 (7)

Se—C8	1.9202 (19)	C8—C13	1.400 (2)
Se—C7	1.9224 (19)	C9—C10	1.388 (3)
O1—C2	1.368 (2)	C9—H9	0.9500
O1—C1	1.434 (2)	C10—C11	1.387 (3)
N1—C14	1.351 (2)	C10—H10	0.9500
N1—N2	1.365 (2)	C11—C12	1.387 (3)
N1—C13	1.433 (2)	C11—H11	0.9500
N2—N3	1.313 (2)	C12—C13	1.388 (3)
N3—C15	1.369 (2)	C12—H12	0.9500
C1—H1A	0.9800	C14—C15	1.378 (2)
C1—H1B	0.9800	C14—H14	0.9500
C1—H1C	0.9800	C15—C16	1.467 (2)
C2—C3	1.388 (3)	C16—C21	1.392 (3)
C2—C7	1.404 (3)	C16—C17	1.402 (2)
C3—C4	1.389 (3)	C17—C18	1.390 (3)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.380 (3)	C18—C19	1.385 (3)
C4—H4	0.9500	C18—H18	0.9500
C5—C6	1.390 (3)	C19—C20	1.388 (3)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.388 (3)	C20—C21	1.390 (3)
C6—H6	0.9500	C20—H20	0.9500
C8—C9	1.393 (3)	C21—H21	0.9500
C8—Se—C7	96.32 (8)	C11—C10—C9	119.82 (18)
C2—O1—C1	117.14 (16)	C11—C10—H10	120.1
C14—N1—N2	110.78 (14)	C9—C10—H10	120.1
C14—N1—C13	130.06 (15)	C12—C11—C10	119.69 (19)
N2—N1—C13	118.87 (15)	C12—C11—H11	120.2
N3—N2—N1	106.67 (14)	C10—C11—H11	120.2
N2—N3—C15	109.61 (14)	C11—C12—C13	120.24 (18)
O1—C1—H1A	109.5	C11—C12—H12	119.9
O1—C1—H1B	109.5	C13—C12—H12	119.9
H1A—C1—H1B	109.5	C12—C13—C8	120.86 (16)
O1—C1—H1C	109.5	C12—C13—N1	116.82 (16)
H1A—C1—H1C	109.5	C8—C13—N1	122.32 (16)
H1B—C1—H1C	109.5	N1—C14—C15	104.97 (16)
O1—C2—C3	125.05 (17)	N1—C14—H14	127.5
O1—C2—C7	114.90 (17)	C15—C14—H14	127.5
C3—C2—C7	120.05 (19)	N3—C15—C14	107.96 (16)
C2—C3—C4	119.93 (19)	N3—C15—C16	122.74 (15)
C2—C3—H3	120.0	C14—C15—C16	129.29 (17)
C4—C3—H3	120.0	C21—C16—C17	118.71 (17)
C5—C4—C3	120.32 (19)	C21—C16—C15	121.23 (16)
C5—C4—H4	119.8	C17—C16—C15	120.06 (17)
C3—C4—H4	119.8	C18—C17—C16	120.19 (18)
C4—C5—C6	120.0 (2)	C18—C17—H17	119.9
C4—C5—H5	120.0	C16—C17—H17	119.9
C6—C5—H5	120.0	C19—C18—C17	120.64 (17)
C7—C6—C5	120.45 (19)	C19—C18—H18	119.7
C7—C6—H6	119.8	C17—C18—H18	119.7
C5—C6—H6	119.8	C18—C19—C20	119.46 (18)
C6—C7—C2	119.22 (18)	C18—C19—H19	120.3
C6—C7—Se	125.27 (14)	C20—C19—H19	120.3
C2—C7—Se	115.50 (15)	C19—C20—C21	120.26 (18)
C9—C8—C13	117.89 (17)	C19—C20—H20	119.9
C9—C8—Se	117.98 (14)	C21—C20—H20	119.9
C13—C8—Se	123.97 (14)	C20—C21—C16	120.73 (17)
C10—C9—C8	121.44 (18)	C20—C21—H21	119.6
C10—C9—H9	119.3	C16—C21—H21	119.6
C8—C9—H9	119.3
C14—N1—N2—N3	−0.75 (19)	C9—C8—C13—N1	−177.53 (17)
C13—N1—N2—N3	−175.16 (14)	Se—C8—C13—N1	7.1 (3)
N1—N2—N3—C15	0.31 (19)	C14—N1—C13—C12	−133.19 (19)
C1—O1—C2—C3	2.6 (3)	N2—N1—C13—C12	40.0 (2)
C1—O1—C2—C7	−178.26 (16)	C14—N1—C13—C8	46.3 (3)
O1—C2—C3—C4	179.81 (17)	N2—N1—C13—C8	−140.54 (18)
C7—C2—C3—C4	0.7 (3)	N2—N1—C14—C15	0.86 (19)
C2—C3—C4—C5	−0.9 (3)	C13—N1—C14—C15	174.46 (17)
C3—C4—C5—C6	0.4 (3)	N2—N3—C15—C14	0.2 (2)
C4—C5—C6—C7	0.2 (3)	N2—N3—C15—C16	179.29 (16)
C5—C6—C7—C2	−0.5 (3)	N1—C14—C15—N3	−0.65 (19)
C5—C6—C7—Se	−179.52 (14)	N1—C14—C15—C16	−179.64 (17)
O1—C2—C7—C6	−179.22 (16)	N3—C15—C16—C21	162.95 (17)
C3—C2—C7—C6	0.0 (3)	C14—C15—C16—C21	−18.2 (3)
O1—C2—C7—Se	−0.1 (2)	N3—C15—C16—C17	−17.9 (3)
C3—C2—C7—Se	179.15 (13)	C14—C15—C16—C17	161.00 (18)
C13—C8—C9—C10	−2.4 (3)	C21—C16—C17—C18	−0.2 (3)
Se—C8—C9—C10	173.23 (15)	C15—C16—C17—C18	−179.43 (17)
C8—C9—C10—C11	0.9 (3)	C16—C17—C18—C19	0.0 (3)
C9—C10—C11—C12	1.1 (3)	C17—C18—C19—C20	0.2 (3)
C10—C11—C12—C13	−1.5 (3)	C18—C19—C20—C21	−0.2 (3)
C11—C12—C13—C8	0.0 (3)	C19—C20—C21—C16	0.0 (3)
C11—C12—C13—N1	179.48 (17)	C17—C16—C21—C20	0.2 (3)
C9—C8—C13—C12	1.9 (3)	C15—C16—C21—C20	179.44 (17)
Se—C8—C13—C12	−173.39 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1i	0.95	2.54	3.472 (2)	165
C14—H14···N3ii	0.95	2.58	3.520 (2)	170
C10—H10···Cg1iii	0.95	2.82	3.630 (2)	144

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C1C6 ring.

DHA	DH	HA	D A	DHA
C18H18O1i	0.95	2.54	3.472(2)	165
C14H14N3ii	0.95	2.58	3.520(2)	170
C10H10Cg1iii	0.95	2.82	3.630(2)	144

Symmetry codes: (i) ; (ii) ; (iii) .