1,4-Bis(1H-benzotriazol-1-yl­methyl)­benzene tetrahydrate

Molecules of the title compound, C₂₀H₁₆N₆.4H₂O, lie across crystallographic inversion centres. The dihedral angle between each benzotriazole moiety and the central benzene ring is 74.95 (9)°. In the crystal structure, the molecular organization is stabilized by well defined weak C—H...π, π–π, O—H...O and O—H...N intermolecular interactions, leading to the formation of a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.069
• wR factor = 0.228
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   N2      ..      12.20 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     -   N3      ..      12.42 su

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         N2
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A    ..  CG1     ..       3.01 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

1,4-Bis(1H-benzotriazol-1-ylmethyl))benzene tetrahydrate

Crystal data

C20H16N6·4H2O	F(000) = 436
Mr = 412.45	Dx = 1.280 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1599 reflections
a = 4.8087 (17) Å	θ = 4.0–55.2°
b = 12.043 (4) Å	µ = 0.09 mm^−1
c = 18.481 (6) Å	T = 298 K
β = 91.160 (8)°	Prism, colourless
V = 1070.1 (6) Å^3	0.28 × 0.12 × 0.10 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	2471 independent reflections
Radiation source: fine-focus sealed tube	1044 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −6→6
Tmin = 0.975, Tmax = 0.991	k = −15→15
6843 measured reflections	l = −12→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.228	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ^2(Fo^2) + (0.1329P)^2] where P = (Fo^2 + 2Fc^2)/3
2471 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.29 e Å^−3
6 restraints	Δρmin = −0.32 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.

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
O1W	0.1978 (6)	0.3778 (2)	0.50601 (15)	0.0959 (9)
H1WA	0.217 (9)	0.436 (2)	0.4804 (19)	0.144*
H1WB	0.067 (7)	0.391 (3)	0.536 (2)	0.144*
O2W	0.2088 (6)	0.0750 (3)	0.07344 (14)	0.1003 (9)
H2WA	0.033 (3)	0.087 (4)	0.070 (2)	0.151*
H2WB	0.251 (8)	0.087 (4)	0.1175 (9)	0.151*
N1	0.2336 (5)	0.14415 (18)	0.33501 (12)	0.0570 (6)
N2	0.1633 (7)	0.0853 (3)	0.27423 (18)	0.0951 (10)
N3	0.3022 (6)	0.1165 (2)	0.21710 (14)	0.0735 (8)
C1	0.4755 (6)	0.2014 (3)	0.24211 (15)	0.0610 (8)
C2	0.6654 (7)	0.2657 (3)	0.20446 (18)	0.0734 (9)
H2	0.6944	0.2545	0.1554	0.088*
C3	0.8076 (7)	0.3458 (3)	0.2424 (2)	0.0815 (10)
H3	0.9364	0.3896	0.2187	0.098*
C4	0.7640 (7)	0.3630 (3)	0.3149 (2)	0.0791 (10)
H4	0.8648	0.4183	0.3388	0.095*
C5	0.5760 (6)	0.3012 (3)	0.35340 (17)	0.0657 (8)
H5	0.5467	0.3134	0.4023	0.079*
C6	0.4338 (6)	0.2200 (2)	0.31489 (14)	0.0534 (7)
C7	0.1210 (6)	0.1262 (3)	0.40741 (15)	0.0659 (8)
H7A	−0.0543	0.0867	0.4029	0.079*
H7B	0.0846	0.1975	0.4297	0.079*
C8	0.3181 (6)	0.0607 (2)	0.45562 (14)	0.0542 (7)
C9	0.3647 (6)	−0.0515 (2)	0.44349 (14)	0.0620 (8)
H9	0.2734	−0.0870	0.4051	0.074*
C10	0.4570 (7)	0.1103 (2)	0.51281 (15)	0.0625 (8)
H10	0.4288	0.1854	0.5219	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1W	0.111 (2)	0.0826 (16)	0.0944 (19)	0.0168 (15)	0.0039 (14)	0.0044 (13)
O2W	0.105 (2)	0.118 (2)	0.0776 (16)	−0.0017 (17)	0.0083 (14)	−0.0199 (15)
N1	0.0585 (15)	0.0623 (15)	0.0499 (13)	0.0051 (12)	−0.0025 (10)	0.0040 (11)
N2	0.105 (3)	0.092 (2)	0.088 (2)	0.0141 (18)	−0.0129 (19)	0.0025 (18)
N3	0.090 (2)	0.0741 (18)	0.0565 (16)	0.0090 (15)	−0.0008 (14)	−0.0023 (13)
C1	0.0611 (19)	0.0638 (19)	0.0580 (18)	0.0170 (15)	0.0000 (14)	0.0059 (14)
C2	0.073 (2)	0.081 (2)	0.0668 (19)	0.0218 (19)	0.0130 (16)	0.0169 (18)
C3	0.071 (2)	0.082 (3)	0.092 (3)	0.0089 (19)	0.0136 (19)	0.026 (2)
C4	0.070 (2)	0.064 (2)	0.103 (3)	−0.0049 (17)	−0.010 (2)	0.0101 (19)
C5	0.066 (2)	0.0662 (19)	0.0647 (18)	0.0054 (16)	−0.0029 (15)	0.0048 (16)
C6	0.0488 (16)	0.0557 (17)	0.0555 (17)	0.0113 (13)	−0.0003 (12)	0.0068 (13)
C7	0.0605 (18)	0.075 (2)	0.0628 (18)	0.0092 (15)	0.0076 (14)	0.0179 (14)
C8	0.0516 (16)	0.0578 (17)	0.0536 (16)	0.0043 (13)	0.0106 (12)	0.0121 (13)
C9	0.0701 (19)	0.0603 (18)	0.0555 (17)	−0.0020 (16)	−0.0004 (14)	0.0001 (14)
C10	0.082 (2)	0.0466 (15)	0.0586 (17)	0.0089 (15)	0.0049 (15)	0.0033 (13)

Geometric parameters (Å, º)

O1W—H1WA	0.85 (3)	C3—H3	0.93
O1W—H1WB	0.86 (4)	C4—C5	1.380 (4)
O2W—H2WA	0.85 (3)	C4—H4	0.93
O2W—H2WB	0.85 (2)	C5—C6	1.382 (4)
N1—N2	1.365 (3)	C5—H5	0.93
N1—C6	1.383 (3)	C7—C8	1.510 (4)
N1—C7	1.470 (4)	C7—H7A	0.97
N2—N3	1.316 (4)	C7—H7B	0.97
N3—C1	1.393 (4)	C8—C10	1.375 (4)
C1—C6	1.382 (4)	C8—C9	1.389 (4)
C1—C2	1.394 (5)	C9—C10^i	1.364 (4)
C2—C3	1.368 (5)	C9—H9	0.93
C2—H2	0.93	C10—C9^i	1.364 (4)
C3—C4	1.377 (5)	C10—H10	0.93
H1WA—O1W—H1WB	107 (2)	C4—C5—H5	122.0
H2WA—O2W—H2WB	105 (2)	C6—C5—H5	122.0
N2—N1—C6	106.5 (2)	C1—C6—C5	122.4 (3)
N2—N1—C7	125.7 (3)	C1—C6—N1	105.7 (3)
C6—N1—C7	127.8 (2)	C5—C6—N1	131.9 (3)
N3—N2—N1	113.0 (3)	N1—C7—C8	112.0 (2)
N2—N3—C1	104.7 (3)	N1—C7—H7A	109.2
C6—C1—N3	110.1 (3)	C8—C7—H7A	109.2
C6—C1—C2	120.4 (3)	N1—C7—H7B	109.2
N3—C1—C2	129.5 (3)	C8—C7—H7B	109.2
C3—C2—C1	117.5 (3)	H7A—C7—H7B	107.9
C3—C2—H2	121.3	C10—C8—C9	118.0 (2)
C1—C2—H2	121.3	C10—C8—C7	121.1 (3)
C2—C3—C4	121.4 (3)	C9—C8—C7	120.9 (3)
C2—C3—H3	119.3	C10^i—C9—C8	120.7 (3)
C4—C3—H3	119.3	C10^i—C9—H9	119.6
C3—C4—C5	122.3 (3)	C8—C9—H9	119.6
C3—C4—H4	118.8	C9^i—C10—C8	121.3 (3)
C5—C4—H4	118.8	C9^i—C10—H10	119.3
C4—C5—C6	116.0 (3)	C8—C10—H10	119.3
C6—N1—N2—N3	0.3 (3)	C4—C5—C6—C1	−0.2 (4)
C7—N1—N2—N3	−178.0 (2)	C4—C5—C6—N1	−179.7 (3)
N1—N2—N3—C1	0.1 (3)	N2—N1—C6—C1	−0.6 (3)
N2—N3—C1—C6	−0.5 (3)	C7—N1—C6—C1	177.7 (2)
N2—N3—C1—C2	−179.0 (3)	N2—N1—C6—C5	179.0 (3)
C6—C1—C2—C3	0.5 (4)	C7—N1—C6—C5	−2.7 (5)
N3—C1—C2—C3	179.0 (3)	N2—N1—C7—C8	100.5 (3)
C1—C2—C3—C4	−0.4 (5)	C6—N1—C7—C8	−77.5 (3)
C2—C3—C4—C5	0.0 (5)	N1—C7—C8—C10	109.1 (3)
C3—C4—C5—C6	0.3 (4)	N1—C7—C8—C9	−70.9 (3)
N3—C1—C6—C5	−179.0 (2)	C10—C8—C9—C10^i	0.0 (4)
C2—C1—C6—C5	−0.3 (4)	C7—C8—C9—C10^i	−180.0 (3)
N3—C1—C6—N1	0.7 (3)	C9—C8—C10—C9^i	0.0 (4)
C2—C1—C6—N1	179.4 (2)	C7—C8—C10—C9^i	180.0 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2W^ii	0.85 (3)	1.98 (3)	2.833 (4)	175 (2)
O1W—H1WB···O2W^iii	0.86 (4)	1.91 (3)	2.743 (4)	161 (3)
O2W—H2WA···O1W^iv	0.85 (3)	2.02 (2)	2.791 (4)	148 (3)
O2W—H2WB···N3	0.85 (2)	1.89 (2)	2.730 (4)	174 (4)
C7—H7A···Cg1^v	0.97	3.01	3.790 (3)	138

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