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The triazole molecule of the title dihydrate, C
16H
28N
6O
2·2H
2O, possesses a crystallographically imposed centre of symmetry and shows normal values of bond lengths and angles. The uncoordinated water molecules are involved in intermolecular N—H
O, O—H
O and O—H
N hydrogen bonds, which stabilize the crystal packing.
Supporting information
CCDC reference: 620778
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.127
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.13 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.55 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C7 .. 6.38 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C16 H28 N6 O2
Alert level G
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
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 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
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
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
3,3'-Diisopropyl-4,4'-(hexane-1,6-diyl)bis[1
H-1,2,4-triazol-5(4
H)-one] dihydrate
top
Crystal data top
C16H28N6O2·2H2O | F(000) = 404 |
Mr = 372.47 | Dx = 1.196 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 17113 reflections |
a = 7.7311 (6) Å | θ = 2.5–27.9° |
b = 10.7183 (8) Å | µ = 0.09 mm−1 |
c = 12.691 (1) Å | T = 293 K |
β = 100.416 (6)° | Prism, colourless |
V = 1034.30 (14) Å3 | 0.80 × 0.52 × 0.28 mm |
Z = 2 | |
Data collection top
Stoe IPDS-2 diffractometer | 2033 independent reflections |
Radiation source: fine-focus sealed tube | 1592 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.5° |
ω scans | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −13→13 |
Tmin = 0.976, Tmax = 0.991 | l = −15→15 |
14522 measured reflections | |
Refinement top
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | w = 1/[σ2(Fo2) + (0.077P)2 + 0.2194P] where P = (Fo2 + 2Fc2)/3 |
2033 reflections | (Δ/σ)max < 0.001 |
134 parameters | Δρmax = 0.17 e Å−3 |
2 restraints | Δρmin = −0.18 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
O33 | 0.22173 (18) | 0.08019 (14) | 0.45457 (10) | 0.0664 (4) | |
C1 | −0.5103 (3) | 0.03527 (18) | 0.04995 (14) | 0.0609 (5) | |
C2 | −0.4613 (2) | 0.17211 (17) | 0.04593 (13) | 0.0620 (5) | |
H2A | −0.3405 | 0.1779 | 0.0352 | 0.074* | |
H2B | −0.5352 | 0.2101 | −0.0156 | 0.074* | |
C3 | −0.4796 (2) | 0.24617 (16) | 0.14519 (13) | 0.0581 (4) | |
H3A | −0.4513 | 0.3328 | 0.1343 | 0.070* | |
H3B | −0.6009 | 0.2425 | 0.1552 | 0.070* | |
C4 | −0.4190 (2) | 0.11330 (15) | 0.30993 (12) | 0.0485 (4) | |
C5 | −0.1931 (2) | 0.22782 (16) | 0.28127 (13) | 0.0543 (4) | |
C6 | −0.0868 (3) | 0.3214 (2) | 0.23408 (19) | 0.0820 (7) | |
H6 | −0.1683 | 0.3790 | 0.1901 | 0.098* | |
C7 | 0.0227 (4) | 0.2581 (4) | 0.1619 (2) | 0.1281 (12) | |
H7A | 0.0897 | 0.3197 | 0.1318 | 0.192* | |
H7B | −0.0534 | 0.2153 | 0.1052 | 0.192* | |
H7C | 0.1011 | 0.1993 | 0.2029 | 0.192* | |
C8 | 0.0267 (5) | 0.3968 (3) | 0.3216 (3) | 0.1513 (15) | |
H8A | 0.0932 | 0.4572 | 0.2897 | 0.227* | |
H8B | 0.1057 | 0.3420 | 0.3668 | 0.227* | |
H8C | −0.0470 | 0.4390 | 0.3635 | 0.227* | |
N1 | −0.36536 (16) | 0.20011 (12) | 0.24238 (10) | 0.0488 (3) | |
N4 | −0.27455 (17) | 0.09204 (13) | 0.38336 (10) | 0.0530 (4) | |
H4 | −0.2702 | 0.0398 | 0.4352 | 0.064* | |
N5 | −0.13351 (18) | 0.16312 (14) | 0.36655 (11) | 0.0594 (4) | |
O1 | −0.56779 (15) | 0.06854 (12) | 0.30306 (9) | 0.0641 (4) | |
H1A | −0.433 (3) | −0.0041 (19) | 0.1109 (16) | 0.070 (5)* | |
H1B | −0.632 (3) | 0.031 (2) | 0.0605 (16) | 0.092 (7)* | |
H66 | 0.285 (3) | 0.080 (2) | 0.4058 (15) | 0.080 (7)* | |
H77 | 0.113 (2) | 0.102 (2) | 0.4281 (17) | 0.089 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O33 | 0.0586 (8) | 0.0875 (10) | 0.0545 (7) | 0.0022 (6) | 0.0137 (6) | 0.0191 (6) |
C1 | 0.0656 (11) | 0.0622 (11) | 0.0539 (9) | −0.0010 (8) | 0.0078 (8) | 0.0079 (8) |
C2 | 0.0659 (10) | 0.0615 (11) | 0.0565 (9) | 0.0002 (8) | 0.0054 (7) | 0.0129 (8) |
C3 | 0.0529 (9) | 0.0528 (9) | 0.0663 (10) | 0.0076 (7) | 0.0048 (7) | 0.0120 (8) |
C4 | 0.0500 (8) | 0.0492 (8) | 0.0494 (8) | 0.0006 (6) | 0.0174 (6) | −0.0019 (6) |
C5 | 0.0472 (8) | 0.0521 (9) | 0.0641 (10) | 0.0016 (7) | 0.0114 (7) | 0.0132 (7) |
C6 | 0.0545 (10) | 0.0805 (14) | 0.1088 (16) | −0.0048 (9) | 0.0087 (10) | 0.0484 (12) |
C7 | 0.0880 (17) | 0.180 (3) | 0.128 (2) | −0.0145 (19) | 0.0512 (16) | 0.059 (2) |
C8 | 0.158 (3) | 0.119 (3) | 0.174 (3) | −0.087 (2) | 0.019 (2) | 0.013 (2) |
N1 | 0.0468 (7) | 0.0482 (7) | 0.0522 (7) | 0.0021 (5) | 0.0111 (5) | 0.0067 (5) |
N4 | 0.0542 (8) | 0.0573 (8) | 0.0498 (7) | −0.0023 (6) | 0.0157 (6) | 0.0096 (6) |
N5 | 0.0495 (7) | 0.0625 (9) | 0.0654 (8) | −0.0048 (6) | 0.0086 (6) | 0.0144 (7) |
O1 | 0.0525 (7) | 0.0738 (8) | 0.0693 (7) | −0.0106 (6) | 0.0195 (5) | 0.0051 (6) |
Geometric parameters (Å, º) top
O33—H66 | 0.853 (16) | C5—N5 | 1.298 (2) |
O33—H77 | 0.878 (16) | C5—N1 | 1.367 (2) |
C1—C1i | 1.509 (4) | C5—C6 | 1.489 (2) |
C1—C2 | 1.518 (3) | C6—C7 | 1.516 (4) |
C1—H1A | 0.98 (2) | C6—C8 | 1.518 (4) |
C1—H1B | 0.98 (2) | C6—H6 | 0.9800 |
C2—C3 | 1.517 (3) | C7—H7A | 0.9600 |
C2—H2A | 0.9700 | C7—H7B | 0.9600 |
C2—H2B | 0.9700 | C7—H7C | 0.9600 |
C3—N1 | 1.467 (2) | C8—H8A | 0.9600 |
C3—H3A | 0.9700 | C8—H8B | 0.9600 |
C3—H3B | 0.9700 | C8—H8C | 0.9600 |
C4—O1 | 1.2346 (19) | N4—N5 | 1.3780 (19) |
C4—N4 | 1.339 (2) | N4—H4 | 0.8600 |
C4—N1 | 1.379 (2) | | |
| | | |
H66—O33—H77 | 110.6 (19) | C5—C6—C7 | 110.5 (2) |
C1i—C1—C2 | 113.03 (18) | C5—C6—C8 | 110.6 (2) |
C1i—C1—H1A | 107.8 (11) | C7—C6—C8 | 111.6 (2) |
C2—C1—H1A | 108.8 (12) | C5—C6—H6 | 108.0 |
C1i—C1—H1B | 110.0 (13) | C7—C6—H6 | 108.0 |
C2—C1—H1B | 107.7 (15) | C8—C6—H6 | 108.0 |
H1A—C1—H1B | 109.4 (17) | C6—C7—H7A | 109.5 |
C3—C2—C1 | 114.62 (14) | C6—C7—H7B | 109.5 |
C3—C2—H2A | 108.6 | H7A—C7—H7B | 109.5 |
C1—C2—H2A | 108.6 | C6—C7—H7C | 109.5 |
C3—C2—H2B | 108.6 | H7A—C7—H7C | 109.5 |
C1—C2—H2B | 108.6 | H7B—C7—H7C | 109.5 |
H2A—C2—H2B | 107.6 | C6—C8—H8A | 109.5 |
N1—C3—C2 | 112.96 (14) | C6—C8—H8B | 109.5 |
N1—C3—H3A | 109.0 | H8A—C8—H8B | 109.5 |
C2—C3—H3A | 109.0 | C6—C8—H8C | 109.5 |
N1—C3—H3B | 109.0 | H8A—C8—H8C | 109.5 |
C2—C3—H3B | 109.0 | H8B—C8—H8C | 109.5 |
H3A—C3—H3B | 107.8 | C5—N1—C4 | 107.77 (12) |
O1—C4—N4 | 129.23 (15) | C5—N1—C3 | 129.03 (13) |
O1—C4—N1 | 126.83 (15) | C4—N1—C3 | 123.16 (13) |
N4—C4—N1 | 103.93 (13) | C4—N4—N5 | 112.47 (12) |
N5—C5—N1 | 111.15 (14) | C4—N4—H4 | 123.8 |
N5—C5—C6 | 123.85 (15) | N5—N4—H4 | 123.8 |
N1—C5—C6 | 124.99 (14) | C5—N5—N4 | 104.66 (13) |
| | | |
C1i—C1—C2—C3 | −179.8 (2) | N4—C4—N1—C5 | −1.55 (17) |
C1—C2—C3—N1 | 61.4 (2) | O1—C4—N1—C3 | −4.6 (2) |
N5—C5—C6—C7 | 83.9 (3) | N4—C4—N1—C3 | 176.35 (14) |
N1—C5—C6—C7 | −97.3 (2) | C2—C3—N1—C5 | 85.0 (2) |
N5—C5—C6—C8 | −40.3 (3) | C2—C3—N1—C4 | −92.48 (18) |
N1—C5—C6—C8 | 138.5 (2) | O1—C4—N4—N5 | −177.82 (16) |
N5—C5—N1—C4 | 1.42 (19) | N1—C4—N4—N5 | 1.23 (17) |
C6—C5—N1—C4 | −177.52 (18) | N1—C5—N5—N4 | −0.64 (19) |
N5—C5—N1—C3 | −176.32 (15) | C6—C5—N5—N4 | 178.32 (18) |
C6—C5—N1—C3 | 4.7 (3) | C4—N4—N5—C5 | −0.41 (18) |
O1—C4—N1—C5 | 177.53 (16) | | |
Symmetry code: (i) −x−1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O33ii | 0.86 | 1.89 | 2.7389 (18) | 170 |
O33—H66···O1iii | 0.85 (2) | 1.89 (2) | 2.7372 (17) | 176 (2) |
O33—H77···N5 | 0.88 (2) | 2.03 (2) | 2.9105 (19) | 177 (2) |
Symmetry codes: (ii) −x, −y, −z+1; (iii) x+1, y, z. |
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