1-Amino-2,5-bis­(4-methoxy­benz­yl)-1,3,4-triazole

In the title compound, C₁₈H₂₀N₄O₂, the triazole ring is twisted with respect to the two benzene rings with dihedral angles of 71.5 (3) and 67.3 (3)°. N—H...N hydrogen bonding occurs between neighboring mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.076
• wR factor = 0.202
• Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         91 PerFi

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.88
PLAT113_ALERT_2_C ADDSYM Suggests Possible Pseudo/New Spacegroup .       C2/c
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT420_ALERT_2_C D-H Without Acceptor       N6     -   H6B    ...          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.50
           From the CIF: _reflns_number_total               1734
           Count of symmetry unique reflns         1755
           Completeness (_total/calc)             98.80%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999); software used to prepare material for publication: SHELXL97.

1-Amino-2,5-bis(4-methoxybenzyl)-1,3,4-triazole

Crystal data

C18H20N4O2	F(000) = 688
Mr = 324.38	Dx = 1.276 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 985 reflections
a = 31.906 (16) Å	θ = 3.3–22.3°
b = 6.130 (3) Å	µ = 0.09 mm^−1
c = 8.726 (4) Å	T = 293 K
β = 98.428 (7)°	Prism, colorless
V = 1688.3 (15) Å^3	0.10 × 0.08 × 0.05 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1100 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
Graphite monochromator	θmax = 26.5°, θmin = 2.5°
φ and ω scans	h = −40→39
3808 measured reflections	k = −6→7
1734 independent reflections	l = −10→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.076	H-atom parameters constrained
wR(F^2) = 0.202	w = 1/[σ^2(Fo^2) + (0.1234P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
1734 reflections	Δρmax = 0.24 e Å^−3
220 parameters	Δρmin = −0.27 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (5)

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.42076 (14)	0.2013 (8)	1.1120 (5)	0.0799 (15)
O2	0.00628 (15)	0.7850 (9)	0.4327 (6)	0.0876 (16)
N1	0.21575 (15)	0.4401 (6)	0.7684 (5)	0.0485 (11)
C2	0.24729 (17)	0.4823 (9)	0.6830 (6)	0.0517 (13)
N3	0.24804 (16)	0.6921 (7)	0.6531 (7)	0.0643 (13)
N4	0.21485 (17)	0.7873 (7)	0.7202 (7)	0.0669 (14)
C5	0.19541 (17)	0.6344 (9)	0.7833 (7)	0.0524 (13)
N6	0.20324 (17)	0.2399 (7)	0.8271 (7)	0.0654 (14)
H6A	0.2163	0.1217	0.8101	0.079*
H6B	0.1825	0.2360	0.8800	0.079*
C7	0.27864 (19)	0.3190 (10)	0.6410 (8)	0.0614 (16)
H7A	0.2896	0.3688	0.5490	0.074*
H7B	0.2644	0.1810	0.6165	0.074*
C8	0.31576 (15)	0.2838 (9)	0.7719 (6)	0.0499 (13)
C9	0.34469 (18)	0.4496 (9)	0.8133 (7)	0.0584 (15)
H9	0.3407	0.5839	0.7636	0.070*
C10	0.37928 (19)	0.4203 (10)	0.9265 (8)	0.0664 (17)
H10	0.3984	0.5337	0.9520	0.080*
C11	0.38548 (18)	0.2189 (10)	1.0032 (7)	0.0582 (14)
C12	0.35617 (18)	0.0524 (10)	0.9621 (7)	0.0597 (15)
H12	0.3598	−0.0827	1.0108	0.072*
C13	0.32192 (17)	0.0878 (10)	0.8500 (7)	0.0625 (16)
H13	0.3023	−0.0236	0.8259	0.075*
C14	0.4324 (3)	−0.0112 (14)	1.1713 (10)	0.086 (2)
H14A	0.4094	−0.0732	1.2160	0.129*
H14B	0.4569	−0.0002	1.2491	0.129*
H14C	0.4388	−0.1029	1.0885	0.129*
C15	0.1572 (2)	0.6620 (12)	0.8651 (7)	0.0642 (17)
H15A	0.1616	0.7858	0.9349	0.077*
H15B	0.1539	0.5330	0.9265	0.077*
C16	0.11700 (18)	0.6979 (9)	0.7494 (7)	0.0578 (15)
C17	0.10965 (18)	0.8934 (10)	0.6700 (8)	0.0663 (18)
H17	0.1297	1.0041	0.6876	0.080*
C18	0.0732 (2)	0.9287 (10)	0.5650 (8)	0.0673 (17)
H18	0.0688	1.0630	0.5155	0.081*
C19	0.04360 (18)	0.7667 (10)	0.5340 (7)	0.0587 (15)
C20	0.0503 (2)	0.5697 (11)	0.6106 (9)	0.077 (2)
H20	0.0302	0.4593	0.5920	0.093*
C21	0.0864 (2)	0.5361 (10)	0.7143 (8)	0.0686 (18)
H21	0.0906	0.4010	0.7626	0.082*
C22	−0.0040 (2)	0.9885 (14)	0.3612 (10)	0.092 (3)
H22A	−0.0048	1.0980	0.4393	0.138*
H22B	−0.0312	0.9791	0.2978	0.138*
H22C	0.0171	1.0267	0.2980	0.138*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.060 (3)	0.077 (3)	0.095 (4)	0.004 (2)	−0.016 (3)	−0.006 (2)
O2	0.058 (3)	0.088 (3)	0.108 (4)	−0.006 (2)	−0.018 (3)	−0.004 (3)
N1	0.053 (2)	0.044 (2)	0.047 (2)	0.008 (2)	0.0024 (19)	0.002 (2)
C2	0.047 (3)	0.054 (3)	0.051 (3)	0.000 (2)	−0.002 (2)	−0.001 (2)
N3	0.058 (3)	0.049 (2)	0.084 (4)	−0.001 (2)	0.003 (3)	−0.001 (2)
N4	0.072 (3)	0.040 (2)	0.090 (4)	0.014 (2)	0.014 (3)	−0.001 (2)
C5	0.050 (3)	0.050 (3)	0.055 (3)	0.005 (2)	0.000 (2)	−0.004 (2)
N6	0.064 (3)	0.043 (2)	0.091 (4)	−0.002 (2)	0.020 (3)	0.001 (2)
C7	0.054 (3)	0.061 (3)	0.067 (4)	0.010 (3)	0.000 (3)	−0.008 (3)
C8	0.042 (3)	0.049 (3)	0.059 (4)	0.005 (2)	0.009 (3)	−0.005 (3)
C9	0.051 (3)	0.043 (3)	0.082 (4)	−0.001 (2)	0.013 (3)	0.005 (3)
C10	0.048 (3)	0.050 (3)	0.099 (5)	−0.007 (3)	0.003 (3)	−0.009 (3)
C11	0.049 (3)	0.066 (3)	0.061 (4)	0.004 (3)	0.009 (3)	−0.007 (3)
C12	0.049 (3)	0.057 (4)	0.073 (4)	−0.004 (3)	0.009 (3)	0.006 (3)
C13	0.043 (3)	0.055 (3)	0.087 (5)	−0.009 (3)	0.000 (3)	0.003 (3)
C14	0.068 (4)	0.107 (6)	0.080 (5)	0.005 (4)	−0.005 (4)	0.015 (4)
C15	0.069 (4)	0.081 (4)	0.044 (3)	0.021 (3)	0.016 (3)	−0.006 (3)
C16	0.054 (3)	0.052 (3)	0.070 (4)	0.009 (3)	0.020 (3)	−0.003 (3)
C17	0.047 (3)	0.052 (3)	0.095 (5)	−0.006 (3)	−0.003 (3)	0.003 (3)
C18	0.055 (3)	0.057 (4)	0.089 (5)	0.002 (3)	0.009 (3)	0.015 (3)
C19	0.048 (3)	0.064 (4)	0.065 (4)	0.001 (3)	0.011 (3)	−0.005 (3)
C20	0.061 (4)	0.057 (4)	0.111 (6)	−0.007 (3)	0.006 (4)	−0.006 (4)
C21	0.072 (4)	0.051 (3)	0.087 (5)	0.006 (3)	0.026 (4)	0.006 (3)
C22	0.061 (4)	0.104 (6)	0.104 (6)	0.004 (4)	−0.014 (4)	0.015 (5)

Geometric parameters (Å, º)

O1—C11	1.366 (7)	C11—C12	1.395 (8)
O1—C14	1.431 (9)	C12—C13	1.373 (8)
O2—C19	1.380 (7)	C12—H12	0.9300
O2—C22	1.411 (9)	C13—H13	0.9300
N1—C2	1.362 (7)	C14—H14A	0.9599
N1—C5	1.371 (7)	C14—H14B	0.9599
N1—N6	1.410 (6)	C14—H14C	0.9599
C2—N3	1.314 (7)	C15—C16	1.528 (8)
C2—C7	1.498 (8)	C15—H15A	0.9700
N3—N4	1.409 (7)	C15—H15B	0.9700
N4—C5	1.291 (8)	C16—C17	1.388 (8)
C5—C15	1.510 (8)	C16—C21	1.393 (9)
N6—H6A	0.8600	C17—C18	1.389 (9)
N6—H6B	0.8600	C17—H17	0.9300
C7—C8	1.535 (8)	C18—C19	1.369 (9)
C7—H7A	0.9700	C18—H18	0.9300
C7—H7B	0.9700	C19—C20	1.382 (10)
C8—C13	1.381 (8)	C20—C21	1.373 (10)
C8—C9	1.385 (8)	C20—H20	0.9300
C9—C10	1.381 (8)	C21—H21	0.9300
C9—H9	0.9300	C22—H22A	0.9599
C10—C11	1.404 (9)	C22—H22B	0.9599
C10—H10	0.9300	C22—H22C	0.9599
C11—O1—C14	117.9 (5)	C12—C13—H13	119.0
C19—O2—C22	118.5 (5)	C8—C13—H13	119.0
C2—N1—C5	106.6 (4)	O1—C14—H14A	109.5
C2—N1—N6	129.4 (4)	O1—C14—H14B	109.5
C5—N1—N6	123.9 (4)	H14A—C14—H14B	109.5
N3—C2—N1	109.3 (5)	O1—C14—H14C	109.5
N3—C2—C7	125.0 (6)	H14A—C14—H14C	109.5
N1—C2—C7	125.5 (5)	H14B—C14—H14C	109.5
C2—N3—N4	106.6 (5)	C5—C15—C16	111.2 (5)
C5—N4—N3	108.3 (4)	C5—C15—H15A	109.4
N4—C5—N1	109.1 (5)	C16—C15—H15A	109.4
N4—C5—C15	126.3 (5)	C5—C15—H15B	109.4
N1—C5—C15	124.6 (5)	C16—C15—H15B	109.4
N1—N6—H6A	120.0	H15A—C15—H15B	108.0
N1—N6—H6B	120.0	C17—C16—C21	116.3 (6)
H6A—N6—H6B	120.0	C17—C16—C15	121.2 (5)
C2—C7—C8	112.4 (5)	C21—C16—C15	122.4 (6)
C2—C7—H7A	109.1	C16—C17—C18	121.9 (6)
C8—C7—H7A	109.1	C16—C17—H17	119.1
C2—C7—H7B	109.1	C18—C17—H17	119.1
C8—C7—H7B	109.1	C19—C18—C17	120.3 (6)
H7A—C7—H7B	107.9	C19—C18—H18	119.9
C13—C8—C9	117.9 (5)	C17—C18—H18	119.9
C13—C8—C7	121.9 (5)	C18—C19—O2	124.9 (6)
C9—C8—C7	120.2 (5)	C18—C19—C20	119.1 (6)
C10—C9—C8	121.6 (5)	O2—C19—C20	116.0 (5)
C10—C9—H9	119.2	C21—C20—C19	120.3 (6)
C8—C9—H9	119.2	C21—C20—H20	119.9
C9—C10—C11	119.8 (5)	C19—C20—H20	119.9
C9—C10—H10	120.1	C20—C21—C16	122.1 (6)
C11—C10—H10	120.1	C20—C21—H21	118.9
O1—C11—C12	125.0 (6)	C16—C21—H21	118.9
O1—C11—C10	116.4 (5)	O2—C22—H22A	109.5
C12—C11—C10	118.6 (6)	O2—C22—H22B	109.5
C13—C12—C11	120.0 (6)	H22A—C22—H22B	109.5
C13—C12—H12	120.0	O2—C22—H22C	109.5
C11—C12—H12	120.0	H22A—C22—H22C	109.5
C12—C13—C8	122.0 (5)	H22B—C22—H22C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N4^i	0.86	2.19	2.968 (7)	150

Symmetry code: (i) x, y−1, z.