Crystal structure of 1-{2-[(2-meth­oxy­phen­yl)selan­yl]phen­yl}-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 mol­ecule is twisted. The dihedral angle between the Se-bound rings is 85.36 (10)°. A close intra­molecular Se...O contact of 2.8507 (13) Å is noted. In the crystal, C—H...O, C—H...N and C—H...π inter­actions lead to the formation of supra­molecular layers parallel to (011); these stack with no specific inter­molecular inter­actions between them.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.028
• wR factor = 0.064
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00400 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        150 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
   3 ALERT level G = General information/check it is not something unexpected

   1 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

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Related literature

For background to arylseleno-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).

S1. Experimental

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 (10 ml) and letting it stand at room temperature.

S2. Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U_iso(H) = 1.2–1.5U_eq(C).

Computing details

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

	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 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.

1-{2-[(2-Methoxyphenyl)selanyl]phenyl}-4-phenyl-1H-1,2,3-triazole

Crystal data

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) Å^3	0.30 × 0.20 × 0.10 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.064	w = 1/[σ^2(Fo^2) + (0.026P)^2 + 0.4456P] where P = (Fo^2 + 2Fc^2)/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

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1^i	0.95	2.54	3.472 (2)	165
C14—H14···N3^ii	0.95	2.58	3.520 (2)	170
C10—H10···Cg1^iii	0.95	2.82	3.630 (2)	144

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