Crystal structure of 4,5-bis-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole methanol monosolvate.

The title compound, C20H23N3O6·CH3OH, was synthesized by [3 + 2] cyclo-addition of (Z)-2,3-bis-(3,4,5-tri-meth-oxy-phen-yl)acrylo-nitrile with sodium azide and ammonium chloride in DMF/water. The central nitro-gen of the triazole ring is protonated. The dihedral angles between the triazole ring and the 3,4,5-tri-meth-oxy-phenyl ring planes are 34.31 (4) and 45.03 (5)°, while that between the 3,4,5-tri-meth-oxy-phenyl rings is 51.87 (5)°. In the crystal, the mol-ecules, along with two methanol solvent mol-ecules are linked into an R (4) 4(10) centrosymmetric dimer by N-H⋯O and O-H⋯N hydrogen bonds.

Related literature

The synthetic procedure has been described by Madadi et al. (2014 ▶) and by Penthala et al. (2014 ▶). For structure-related activity, see: Young & Chaplin (2004 ▶); Pettit et al. (1995 ▶); Hsieh et al. (2005 ▶); Carr et al. (2010 ▶); Banimustafa et al. (2013 ▶); Demchuk et al. (2014 ▶).

Experimental

Crystal data

C20H23N3O6·CH4O

M = 433.45

Triclinic,

a = 10.1458 (1) Å

b = 10.6090 (1) Å

c = 11.0435 (2) Å

α = 89.5708 (6)°

β = 72.5903 (6)°

γ = 70.7146 (7)°

V = 1065.07 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 90 K

0.24 × 0.22 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.882, T max = 0.970

28813 measured reflections

4887 independent reflections

3960 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.127

S = 1.05

4887 reflections

291 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 2006 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008b ▶); molecular graphics: XP in (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELX (Sheldrick, 2008b ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814020911/sj5427sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814020911/sj5427Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814020911/sj5427Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814020911/sj5427fig1.tif

A view of the asymmetric unit of the structure with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and a hydrogen bond is drawn as a dashed line.

CCDC reference: 1025101

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

C20H23N3O6·CH4O	Z = 2
Mr = 433.45	F(000) = 460
Triclinic, P1	Dx = 1.352 Mg m−3
a = 10.1458 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6090 (1) Å	Cell parameters from 11695 reflections
c = 11.0435 (2) Å	θ = 1.0–27.5°
α = 89.5708 (6)°	µ = 0.10 mm−1
β = 72.5903 (6)°	T = 90 K
γ = 70.7146 (7)°	Block, colourless
V = 1065.07 (2) Å3	0.24 × 0.22 × 0.20 mm

Nonius KappaCCD diffractometer	4887 independent reflections
Radiation source: fine-focus sealed-tube	3960 reflections with I > 2σ(I)
Detector resolution: 9.1 pixels mm-1	Rint = 0.037
φ and ω scans at fixed χ = 55°	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −13→13
Tmin = 0.882, Tmax = 0.970	k = −13→13
28813 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: difference Fourier map
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0731P)2 + 0.3615P] where P = (Fo2 + 2Fc2)/3
4887 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was mounted with polyisobutene oil on the tip of a fine glass fibre, fastened in a copper mounting pin with electrical solder. It was placed directly into the cold stream of a liquid nitrogen based cryostat.Diffraction data were collected with the crystal at 90 K, which is standard practice in this laboratory for the majority of flash-cooled crystals.

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
N1	0.60782 (12)	0.74167 (11)	0.56615 (11)	0.0185 (2)
N2	0.73493 (13)	0.64285 (12)	0.54691 (11)	0.0195 (3)
H2N	0.8264 (19)	0.6486 (17)	0.5010 (16)	0.023*
N3	0.72437 (12)	0.53382 (11)	0.60414 (11)	0.0182 (2)
O1	0.10274 (10)	1.12766 (9)	0.78293 (10)	0.0199 (2)
O2	−0.09566 (10)	1.00928 (10)	0.79884 (9)	0.0203 (2)
O3	−0.01750 (10)	0.74272 (10)	0.76182 (10)	0.0212 (2)
O4	0.55195 (11)	0.11586 (9)	0.76505 (9)	0.0200 (2)
O5	0.35131 (11)	0.22077 (10)	0.98936 (9)	0.0226 (2)
O6	0.26188 (10)	0.48551 (10)	1.06686 (9)	0.0203 (2)
C1	0.34889 (14)	0.77606 (13)	0.68391 (12)	0.0156 (3)
C2	0.30637 (14)	0.91466 (13)	0.71055 (12)	0.0161 (3)
H2	0.3785	0.9560	0.7006	0.019*
C3	0.15713 (14)	0.99221 (13)	0.75193 (12)	0.0160 (3)
C4	0.05096 (14)	0.93156 (13)	0.76591 (12)	0.0162 (3)
C5	0.09440 (14)	0.79251 (14)	0.74196 (12)	0.0171 (3)
C6	0.24333 (14)	0.71422 (14)	0.69882 (13)	0.0177 (3)
H6	0.2728	0.6199	0.6798	0.021*
C7	0.50685 (14)	0.69379 (13)	0.64045 (12)	0.0162 (3)
C8	0.57985 (14)	0.56334 (13)	0.66514 (12)	0.0159 (3)
C9	0.52294 (14)	0.47110 (13)	0.74808 (13)	0.0162 (3)
C10	0.56894 (14)	0.33457 (13)	0.70935 (13)	0.0167 (3)
H10	0.6368	0.2988	0.6270	0.020*
C11	0.51433 (14)	0.25086 (13)	0.79276 (13)	0.0161 (3)
C12	0.41268 (14)	0.30331 (14)	0.91361 (13)	0.0172 (3)
C13	0.36502 (14)	0.44122 (14)	0.94987 (12)	0.0165 (3)
C14	0.42169 (14)	0.52434 (14)	0.86842 (13)	0.0170 (3)
H14	0.3916	0.6173	0.8946	0.020*
C15	0.20801 (16)	1.19411 (14)	0.76486 (15)	0.0231 (3)
H15A	0.2708	1.1587	0.8184	0.035*
H15B	0.1565	1.2907	0.7887	0.035*
H15C	0.2688	1.1785	0.6751	0.035*
C16	−0.17239 (16)	1.02141 (16)	0.93261 (14)	0.0265 (3)
H16A	−0.1634	0.9319	0.9605	0.040*
H16B	−0.2765	1.0745	0.9489	0.040*
H16C	−0.1297	1.0661	0.9799	0.040*
C17	0.02045 (17)	0.60063 (15)	0.75393 (16)	0.0279 (3)
H17A	0.0798	0.5621	0.6663	0.042*
H17B	−0.0694	0.5778	0.7781	0.042*
H17C	0.0771	0.5642	0.8119	0.042*
C18	0.64600 (16)	0.06014 (15)	0.63927 (14)	0.0242 (3)
H18A	0.6015	0.1072	0.5768	0.036*
H18B	0.6593	−0.0354	0.6287	0.036*
H18C	0.7417	0.0703	0.6259	0.036*
C19	0.38996 (17)	0.19362 (16)	1.10416 (14)	0.0247 (3)
H19A	0.4925	0.1338	1.0826	0.037*
H19B	0.3256	0.1506	1.1593	0.037*
H19C	0.3781	0.2780	1.1489	0.037*
C20	0.19984 (16)	0.62778 (14)	1.10034 (13)	0.0220 (3)
H20A	0.2772	0.6621	1.1044	0.033*
H20B	0.1235	0.6476	1.1837	0.033*
H20C	0.1564	0.6709	1.0358	0.033*
O1M	1.00187 (11)	0.66705 (10)	0.42773 (10)	0.0244 (2)
H1M	1.0849	0.6076	0.4149	0.037*
C1M	1.01117 (17)	0.79571 (15)	0.45053 (15)	0.0269 (3)
H1M1	0.9119	0.8626	0.4814	0.040*
H1M2	1.0672	0.8206	0.3710	0.040*
H1M3	1.0608	0.7922	0.5148	0.040*

	U11	U22	U33	U12	U13	U23
N1	0.0160 (5)	0.0170 (6)	0.0195 (6)	−0.0042 (4)	−0.0029 (4)	0.0023 (5)
N2	0.0155 (5)	0.0163 (6)	0.0228 (6)	−0.0052 (4)	−0.0011 (5)	0.0035 (5)
N3	0.0172 (5)	0.0164 (6)	0.0194 (6)	−0.0070 (4)	−0.0022 (4)	0.0033 (4)
O1	0.0167 (5)	0.0148 (5)	0.0270 (5)	−0.0046 (4)	−0.0063 (4)	0.0008 (4)
O2	0.0127 (4)	0.0229 (5)	0.0217 (5)	−0.0030 (4)	−0.0039 (4)	0.0033 (4)
O3	0.0166 (5)	0.0193 (5)	0.0281 (5)	−0.0088 (4)	−0.0047 (4)	0.0020 (4)
O4	0.0235 (5)	0.0141 (5)	0.0203 (5)	−0.0063 (4)	−0.0039 (4)	0.0011 (4)
O5	0.0322 (6)	0.0247 (5)	0.0171 (5)	−0.0179 (5)	−0.0077 (4)	0.0070 (4)
O6	0.0205 (5)	0.0186 (5)	0.0170 (5)	−0.0062 (4)	0.0003 (4)	0.0006 (4)
C1	0.0150 (6)	0.0161 (6)	0.0139 (6)	−0.0034 (5)	−0.0041 (5)	0.0031 (5)
C2	0.0161 (6)	0.0175 (7)	0.0160 (6)	−0.0074 (5)	−0.0052 (5)	0.0033 (5)
C3	0.0176 (6)	0.0147 (6)	0.0152 (6)	−0.0041 (5)	−0.0062 (5)	0.0030 (5)
C4	0.0138 (6)	0.0180 (7)	0.0156 (6)	−0.0034 (5)	−0.0053 (5)	0.0033 (5)
C5	0.0161 (6)	0.0219 (7)	0.0156 (6)	−0.0087 (5)	−0.0060 (5)	0.0042 (5)
C6	0.0188 (6)	0.0167 (7)	0.0178 (6)	−0.0069 (5)	−0.0054 (5)	0.0025 (5)
C7	0.0169 (6)	0.0164 (7)	0.0144 (6)	−0.0061 (5)	−0.0032 (5)	0.0014 (5)
C8	0.0142 (6)	0.0158 (6)	0.0154 (6)	−0.0043 (5)	−0.0022 (5)	−0.0007 (5)
C9	0.0147 (6)	0.0164 (7)	0.0179 (6)	−0.0050 (5)	−0.0061 (5)	0.0031 (5)
C10	0.0151 (6)	0.0172 (7)	0.0162 (6)	−0.0050 (5)	−0.0033 (5)	0.0012 (5)
C11	0.0167 (6)	0.0138 (6)	0.0195 (6)	−0.0055 (5)	−0.0080 (5)	0.0026 (5)
C12	0.0187 (6)	0.0196 (7)	0.0169 (6)	−0.0106 (5)	−0.0064 (5)	0.0050 (5)
C13	0.0140 (6)	0.0201 (7)	0.0151 (6)	−0.0062 (5)	−0.0040 (5)	0.0022 (5)
C14	0.0168 (6)	0.0153 (6)	0.0186 (6)	−0.0055 (5)	−0.0052 (5)	0.0015 (5)
C15	0.0216 (7)	0.0172 (7)	0.0318 (8)	−0.0079 (6)	−0.0089 (6)	0.0026 (6)
C16	0.0197 (7)	0.0293 (8)	0.0235 (7)	−0.0057 (6)	−0.0001 (6)	0.0031 (6)
C17	0.0246 (7)	0.0220 (8)	0.0373 (9)	−0.0128 (6)	−0.0047 (6)	0.0022 (6)
C18	0.0259 (7)	0.0177 (7)	0.0246 (7)	−0.0079 (6)	−0.0011 (6)	−0.0030 (6)
C19	0.0263 (7)	0.0267 (8)	0.0212 (7)	−0.0093 (6)	−0.0075 (6)	0.0089 (6)
C20	0.0215 (7)	0.0190 (7)	0.0191 (7)	−0.0030 (6)	−0.0017 (5)	−0.0013 (5)
O1M	0.0200 (5)	0.0177 (5)	0.0302 (6)	−0.0046 (4)	−0.0028 (4)	0.0040 (4)
C1M	0.0278 (7)	0.0227 (8)	0.0301 (8)	−0.0100 (6)	−0.0073 (6)	0.0020 (6)

N1—N2	1.3243 (16)	C10—C11	1.3970 (18)
N1—C7	1.3473 (16)	C10—H10	0.9500
N2—N3	1.3339 (16)	C11—C12	1.4010 (19)
N2—H2N	0.936 (17)	C12—C13	1.4002 (19)
N3—C8	1.3455 (16)	C13—C14	1.3895 (18)
O1—C3	1.3628 (16)	C14—H14	0.9500
O1—C15	1.4301 (16)	C15—H15A	0.9800
O2—C4	1.3768 (15)	C15—H15B	0.9800
O2—C16	1.4330 (17)	C15—H15C	0.9800
O3—C5	1.3645 (16)	C16—H16A	0.9800
O3—C17	1.4236 (17)	C16—H16B	0.9800
O4—C11	1.3661 (16)	C16—H16C	0.9800
O4—C18	1.4268 (17)	C17—H17A	0.9800
O5—C12	1.3755 (16)	C17—H17B	0.9800
O5—C19	1.4358 (17)	C17—H17C	0.9800
O6—C13	1.3639 (16)	C18—H18A	0.9800
O6—C20	1.4326 (16)	C18—H18B	0.9800
C1—C2	1.3950 (19)	C18—H18C	0.9800
C1—C6	1.4006 (18)	C19—H19A	0.9800
C1—C7	1.4774 (18)	C19—H19B	0.9800
C2—C3	1.3954 (18)	C19—H19C	0.9800
C2—H2	0.9500	C20—H20A	0.9800
C3—C4	1.3982 (19)	C20—H20B	0.9800
C4—C5	1.3953 (19)	C20—H20C	0.9800
C5—C6	1.3950 (18)	O1M—C1M	1.4282 (18)
C6—H6	0.9500	O1M—H1M	0.8400
C7—C8	1.4057 (19)	C1M—H1M1	0.9800
C8—C9	1.4743 (18)	C1M—H1M2	0.9800
C9—C10	1.3936 (19)	C1M—H1M3	0.9800
C9—C14	1.3970 (18)
N2—N1—C7	104.56 (11)	O6—C13—C12	115.88 (11)
N1—N2—N3	114.49 (11)	C14—C13—C12	120.27 (12)
N1—N2—H2N	124.0 (10)	C13—C14—C9	119.97 (12)
N3—N2—H2N	121.4 (11)	C13—C14—H14	120.0
N2—N3—C8	105.06 (11)	C9—C14—H14	120.0
C3—O1—C15	116.70 (10)	O1—C15—H15A	109.5
C4—O2—C16	113.71 (10)	O1—C15—H15B	109.5
C5—O3—C17	117.30 (11)	H15A—C15—H15B	109.5
C11—O4—C18	116.84 (10)	O1—C15—H15C	109.5
C12—O5—C19	116.01 (11)	H15A—C15—H15C	109.5
C13—O6—C20	116.87 (10)	H15B—C15—H15C	109.5
C2—C1—C6	120.65 (12)	O2—C16—H16A	109.5
C2—C1—C7	119.59 (12)	O2—C16—H16B	109.5
C6—C1—C7	119.77 (12)	H16A—C16—H16B	109.5
C1—C2—C3	119.53 (12)	O2—C16—H16C	109.5
C1—C2—H2	120.2	H16A—C16—H16C	109.5
C3—C2—H2	120.2	H16B—C16—H16C	109.5
O1—C3—C2	124.68 (12)	O3—C17—H17A	109.5
O1—C3—C4	115.06 (11)	O3—C17—H17B	109.5
C2—C3—C4	120.25 (12)	H17A—C17—H17B	109.5
O2—C4—C5	120.10 (11)	O3—C17—H17C	109.5
O2—C4—C3	120.05 (12)	H17A—C17—H17C	109.5
C5—C4—C3	119.81 (12)	H17B—C17—H17C	109.5
O3—C5—C6	124.27 (12)	O4—C18—H18A	109.5
O3—C5—C4	115.33 (11)	O4—C18—H18B	109.5
C6—C5—C4	120.39 (12)	H18A—C18—H18B	109.5
C5—C6—C1	119.32 (12)	O4—C18—H18C	109.5
C5—C6—H6	120.3	H18A—C18—H18C	109.5
C1—C6—H6	120.3	H18B—C18—H18C	109.5
N1—C7—C8	108.49 (11)	O5—C19—H19A	109.5
N1—C7—C1	121.12 (12)	O5—C19—H19B	109.5
C8—C7—C1	130.39 (12)	H19A—C19—H19B	109.5
N3—C8—C7	107.40 (11)	O5—C19—H19C	109.5
N3—C8—C9	121.97 (12)	H19A—C19—H19C	109.5
C7—C8—C9	130.48 (12)	H19B—C19—H19C	109.5
C10—C9—C14	120.46 (12)	O6—C20—H20A	109.5
C10—C9—C8	121.60 (12)	O6—C20—H20B	109.5
C14—C9—C8	117.94 (12)	H20A—C20—H20B	109.5
C9—C10—C11	119.35 (12)	O6—C20—H20C	109.5
C9—C10—H10	120.3	H20A—C20—H20C	109.5
C11—C10—H10	120.3	H20B—C20—H20C	109.5
O4—C11—C10	124.35 (12)	C1M—O1M—H1M	109.5
O4—C11—C12	115.03 (11)	O1M—C1M—H1M1	109.5
C10—C11—C12	120.62 (12)	O1M—C1M—H1M2	109.5
O5—C12—C13	121.12 (12)	H1M1—C1M—H1M2	109.5
O5—C12—C11	119.30 (12)	O1M—C1M—H1M3	109.5
C13—C12—C11	119.29 (12)	H1M1—C1M—H1M3	109.5
O6—C13—C14	123.85 (12)	H1M2—C1M—H1M3	109.5
C7—N1—N2—N3	−0.41 (15)	N2—N3—C8—C9	−175.64 (12)
N1—N2—N3—C8	0.07 (16)	N1—C7—C8—N3	−0.54 (15)
C6—C1—C2—C3	−0.27 (19)	C1—C7—C8—N3	−179.60 (13)
C7—C1—C2—C3	−179.82 (12)	N1—C7—C8—C9	174.91 (13)
C15—O1—C3—C2	3.37 (19)	C1—C7—C8—C9	−4.1 (2)
C15—O1—C3—C4	−177.50 (12)	N3—C8—C9—C10	−47.04 (19)
C1—C2—C3—O1	178.74 (12)	C7—C8—C9—C10	138.07 (15)
C1—C2—C3—C4	−0.36 (19)	N3—C8—C9—C14	132.31 (14)
C16—O2—C4—C5	85.75 (15)	C7—C8—C9—C14	−42.6 (2)
C16—O2—C4—C3	−96.54 (15)	C14—C9—C10—C11	−0.87 (19)
O1—C3—C4—O2	4.99 (18)	C8—C9—C10—C11	178.47 (12)
C2—C3—C4—O2	−175.83 (11)	C18—O4—C11—C10	−4.16 (18)
O1—C3—C4—C5	−177.30 (11)	C18—O4—C11—C12	175.12 (12)
C2—C3—C4—C5	1.9 (2)	C9—C10—C11—O4	−179.85 (12)
C17—O3—C5—C6	8.57 (19)	C9—C10—C11—C12	0.91 (19)
C17—O3—C5—C4	−172.45 (12)	C19—O5—C12—C13	−72.53 (17)
O2—C4—C5—O3	−4.09 (18)	C19—O5—C12—C11	113.70 (14)
C3—C4—C5—O3	178.19 (12)	O4—C11—C12—O5	−4.85 (18)
O2—C4—C5—C6	174.92 (12)	C10—C11—C12—O5	174.46 (11)
C3—C4—C5—C6	−2.79 (19)	O4—C11—C12—C13	−178.74 (11)
O3—C5—C6—C1	−178.92 (12)	C10—C11—C12—C13	0.6 (2)
C4—C5—C6—C1	2.16 (19)	C20—O6—C13—C14	6.21 (18)
C2—C1—C6—C5	−0.6 (2)	C20—O6—C13—C12	−173.47 (11)
C7—C1—C6—C5	178.93 (12)	O5—C12—C13—O6	3.80 (18)
N2—N1—C7—C8	0.56 (15)	C11—C12—C13—O6	177.57 (11)
N2—N1—C7—C1	179.72 (12)	O5—C12—C13—C14	−175.89 (12)
C2—C1—C7—N1	−34.27 (18)	C11—C12—C13—C14	−2.11 (19)
C6—C1—C7—N1	146.18 (13)	O6—C13—C14—C9	−177.50 (12)
C2—C1—C7—C8	144.69 (15)	C12—C13—C14—C9	2.16 (19)
C6—C1—C7—C8	−34.9 (2)	C10—C9—C14—C13	−0.66 (19)
N2—N3—C8—C7	0.28 (15)	C8—C9—C14—C13	179.98 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1M	0.936 (17)	1.797 (18)	2.7303 (15)	174.2 (16)
O1M—H1M···N3i	0.84	1.97	2.8101 (15)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1M	0.936 (17)	1.797 (18)	2.7303 (15)	174.2 (16)
O1M—H1M⋯N3i	0.84	1.97	2.8101 (15)	177

Symmetry code: (i) .