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The crystal structures of two NH-pyrazole derivatives forming intermolecular N—H...N hydrogen bonds are reported: 5-methyl-4-(3-methylpyrazol-5-yl)pyrazol-3-ol, C8H10N4O (P1), and 3-methyl-5-dihydro-1H-naphtho[1,2-d]pyrazole hemihydrochloride, C12H12N2.-C12H13N_{2}^{+}.Cl (P2). 26 other structures are surveyed in order to obtain a deeper insight into the ways NH-pyrazoles self-assemble by means of intermolecular N—H...N hydrogen bonds in molecular crystals. A limited number of compounds form chains or dimers via homonuclear N+—H...N positive-charge-assisted hydrogen bonds, typical of proton sponges, which can be remarkably short [e.g. N...N 2.714 (3), N—H 1.09 (3), H...N 1.63 (3) Å, N—H...N 169 (3)° in (P2)]. Most pyrazoles, however, pack via neutral N—H...N bonds which are formally assisted by resonance (resonance-assisted hydrogen bond, RAHB) through the ...N=C—C=C—NH... iminoenamine fragment, contained in the ring, giving rise to dimers, trimers, tetramers and infinite chains of pyrazole molecules. Surprisingly, the resonance does not appear to shorten the N—H...N bond with respect to the accepted mean value N...N 2.97 (10) Å for non-resonant N—H...N bonds. It is shown that this is due to the internal π-delocalization of the pyrazole ring, which can be hardly increased by the hydrogen-bond interaction, except in symmetrically 3,5-substituted pyrazoles which display N...N distances as short as 2.82 Å, identical C—C and C—N distances in the two halves of the pyrazole molecule, and typical phenomena of N—H...N dynamical proton disorder, detectable by 15N-CP/MAS solid-state NMR.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, P2, P1

fcf

Structure factor file (CIF format)
Contains datablock a:idraz5

fcf

Structure factor file (CIF format)
Contains datablock a:idraz7

CCDC references: 138558; 138559

Computing details top

For both compounds, data collection: CAD4 Enraf-Nonius, 1984; cell refinement: CAD4 Enraf-Nonius, 1984; data reduction: MolEN, C.K. Fair, Enraf-Nonius, 1990; program(s) used to solve structure: SIR92, Altomare et al., 1994; program(s) used to refine structure: SHELX97, Sheldrick, 1997; molecular graphics: ORTEPII, Johnson, 1976; software used to prepare material for publication: PARST (Nardelli, 1983, 1995), SHELX97 (Sheldrick, 1997).

(P1) 3-hydroxy-5-methyl-4-(3'-methylpyrazol-5'-yl)pyrazole top
Crystal data top
C8H10N4OF(000) = 752
Mr = 178.20Dx = 1.398 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 25 reflections
a = 16.409 (3) Åθ = 9–13°
b = 7.619 (1) ŵ = 0.10 mm1
c = 13.544 (6) ÅT = 293 K
V = 1693.3 (8) Å3Prism, colourless
Z = 80.33 × 0.26 × 0.23 mm
Data collection top
Enraf Nonius CAD-4
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 2.5°
Graphite monochromatorh = 020
ω/2θ scansk = 09
1841 measured reflectionsl = 017
1841 independent reflections3 standard reflections every 120 min
1100 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: difference Fourier map
wR(F2) = 0.186All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.1089P)2]
where P = (Fo2 + 2Fc2)/3
1841 reflections(Δ/σ)max = 0.010
158 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.38 e Å3
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
xyzUiso*/Ueq
O10.09348 (11)0.1782 (3)0.17183 (16)0.0522 (6)
N10.09304 (14)0.1704 (3)0.05922 (17)0.0391 (6)
N20.04603 (13)0.1409 (3)0.14028 (16)0.0413 (6)
N30.23325 (14)0.3781 (4)0.05880 (19)0.0481 (7)
N40.17569 (13)0.3032 (4)0.0006 (2)0.0467 (7)
C10.02949 (15)0.1891 (4)0.1115 (2)0.0382 (7)
C20.03050 (15)0.2453 (4)0.01439 (19)0.0343 (6)
C30.05044 (17)0.2328 (4)0.0167 (2)0.0370 (7)
C40.0897 (2)0.2740 (6)0.1127 (3)0.0537 (9)
C50.09975 (15)0.3153 (4)0.0401 (2)0.0354 (6)
C60.10917 (15)0.4001 (4)0.1266 (2)0.0370 (6)
C70.19287 (15)0.4383 (4)0.1362 (2)0.0371 (6)
C80.2364 (2)0.5280 (5)0.2180 (3)0.0491 (8)
H10.077 (2)0.164 (5)0.254 (3)0.073 (11)*
H40.1842 (17)0.256 (4)0.063 (2)0.042 (8)*
H60.0712 (17)0.439 (4)0.176 (2)0.041 (8)*
H100.149 (3)0.137 (6)0.058 (3)0.094 (14)*
H410.067 (3)0.229 (5)0.171 (3)0.077 (13)*
H420.086 (2)0.394 (6)0.121 (3)0.070 (12)*
H430.150 (4)0.244 (7)0.105 (4)0.113 (17)*
H810.242 (3)0.441 (7)0.261 (3)0.098 (16)*
H820.208 (3)0.635 (6)0.241 (3)0.087 (13)*
H830.283 (3)0.587 (7)0.198 (4)0.102 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0277 (10)0.0873 (17)0.0416 (12)0.0052 (10)0.0052 (8)0.0091 (11)
N10.0277 (11)0.0490 (14)0.0405 (13)0.0023 (10)0.0007 (9)0.0009 (11)
N20.0253 (11)0.0592 (16)0.0393 (12)0.0049 (10)0.0001 (9)0.0014 (11)
N30.0261 (12)0.0608 (17)0.0573 (15)0.0038 (10)0.0006 (10)0.0116 (13)
N40.0243 (11)0.0694 (18)0.0463 (14)0.0000 (11)0.0021 (10)0.0133 (14)
C10.0270 (12)0.0501 (16)0.0376 (14)0.0014 (12)0.0018 (11)0.0014 (12)
C20.0245 (12)0.0413 (14)0.0372 (15)0.0014 (10)0.0003 (10)0.0034 (12)
C30.0274 (12)0.0425 (16)0.0412 (16)0.0014 (11)0.0020 (11)0.0044 (12)
C40.0381 (17)0.073 (3)0.050 (2)0.0015 (16)0.0086 (14)0.0069 (18)
C50.0250 (12)0.0418 (15)0.0395 (14)0.0009 (11)0.0005 (11)0.0057 (12)
C60.0260 (13)0.0463 (15)0.0389 (15)0.0035 (11)0.0014 (11)0.0004 (12)
C70.0281 (12)0.0340 (14)0.0493 (16)0.0005 (11)0.0021 (11)0.0032 (12)
C80.0440 (18)0.0442 (19)0.0589 (19)0.0045 (15)0.0086 (15)0.0031 (16)
Geometric parameters (Å, º) top
N1—N21.360 (3)O1—H11.15 (4)
N1—C31.331 (4)N1—H100.96 (5)
N2—C11.350 (3)N4—H40.94 (3)
O1—C11.333 (3)C3—C41.485 (4)
C1—C21.383 (4)C4—H410.93 (4)
C2—C31.397 (4)C4—H420.92 (4)
C2—C51.456 (4)C4—H431.03 (6)
C5—C61.347 (4)C6—H60.96 (3)
N4—C51.359 (3)C7—C81.485 (4)
N3—N41.356 (3)C8—H810.89 (5)
N3—C71.322 (4)C8—H820.99 (5)
C6—C71.410 (4)C8—H830.93 (5)
C1—O1—H1114.4 (18)H41—C4—H42104 (3)
C3—N1—N2112.6 (2)C3—C4—H43107 (3)
C3—N1—H10126 (3)H41—C4—H43113 (4)
N2—N1—H10121 (3)H42—C4—H43107 (4)
C1—N2—N1104.0 (2)C6—C5—N4105.6 (2)
C7—N3—N4104.9 (2)C6—C5—C2134.9 (2)
N3—N4—C5112.4 (2)N4—C5—C2119.4 (3)
N3—N4—H4126.0 (18)C5—C6—C7106.9 (2)
C5—N4—H4121.4 (18)C5—C6—H6132.9 (17)
O1—C1—N2121.9 (2)C7—C6—H6120.2 (16)
O1—C1—C2126.4 (2)N3—C7—C6110.1 (2)
N2—C1—C2111.7 (2)N3—C7—C8120.7 (3)
C1—C2—C3104.7 (2)C6—C7—C8129.2 (3)
C1—C2—C5127.2 (2)C7—C8—H81101 (3)
C3—C2—C5127.9 (2)C7—C8—H82113 (3)
N1—C3—C2106.9 (2)H81—C8—H82118 (4)
N1—C3—C4121.6 (3)C7—C8—H83113 (3)
C2—C3—C4131.5 (3)H81—C8—H83118 (4)
C3—C4—H41119 (2)H82—C8—H8394 (4)
C3—C4—H42107 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O10.94 (3)2.18 (3)2.860 (3)128 (2)
O1—H1···N2i1.15 (4)1.53 (4)2.676 (3)174 (3)
N1—H10···N3ii0.95 (5)1.94 (5)2.874 (3)168 (4)
Symmetry codes: (i) x, y, z1/2; (ii) x1/2, y+1/2, z.
(P2) 4,5-dihydronaphto[1,2-d]-1H,3-methylpyrazole hemihydrochloride top
Crystal data top
C12H12N2·C12H13N2+·ClF(000) = 856
Mr = 404.93Dx = 1.261 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 8.190 (1) Åθ = 9–14°
b = 14.463 (2) ŵ = 0.20 mm1
c = 18.115 (3) ÅT = 293 K
β = 96.20 (1)°Irregular, colourless
V = 2133.2 (5) Å30.55 × 0.19 × 0.12 mm
Z = 4
Data collection top
Enraf Nonius CAD-4
diffractometer
Rint = 0.018
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 2.3°
Graphite monochromatorh = 010
ω/2θ scansk = 018
4977 measured reflectionsl = 2322
4643 independent reflections3 standard reflections every 120 min
2168 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056All H-atom parameters refined
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0484P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.027
4643 reflectionsΔρmax = 0.19 e Å3
363 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0011 (6)
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
xyzUiso*/Ueq
Cl0.36703 (9)0.12467 (5)0.36324 (3)0.0665 (3)
N210.2388 (3)0.03276 (16)0.52045 (12)0.0537 (6)
N110.2104 (3)0.03301 (16)0.44568 (12)0.0533 (6)
C110.1113 (3)0.10410 (18)0.42360 (14)0.0501 (6)
C210.0739 (3)0.14976 (18)0.48611 (15)0.0540 (7)
C310.1559 (3)0.10331 (19)0.54616 (15)0.0545 (7)
C410.1607 (6)0.1214 (4)0.6273 (2)0.0798 (11)
C510.0409 (4)0.2302 (2)0.4810 (2)0.0724 (9)
C610.0496 (5)0.2753 (3)0.4049 (2)0.0825 (11)
C710.0388 (3)0.2116 (2)0.34005 (17)0.0651 (8)
C810.0476 (3)0.12776 (19)0.34814 (15)0.0554 (7)
C910.0665 (4)0.0721 (2)0.28737 (16)0.0637 (8)
C1010.0027 (4)0.0996 (3)0.21711 (19)0.0791 (10)
C1110.0883 (4)0.1812 (3)0.2094 (2)0.0884 (12)
C1210.1074 (4)0.2362 (3)0.2688 (2)0.0808 (10)
N120.4670 (3)0.17333 (15)0.52867 (13)0.0513 (6)
N220.4279 (3)0.10916 (14)0.57844 (11)0.0541 (6)
C120.5353 (3)0.24820 (18)0.56344 (14)0.0496 (6)
C220.5406 (3)0.2321 (2)0.63869 (14)0.0548 (7)
C320.4739 (3)0.1447 (2)0.64561 (14)0.0563 (7)
C420.4526 (6)0.0899 (4)0.71348 (19)0.0815 (11)
C520.6164 (5)0.3018 (2)0.69306 (17)0.0722 (9)
C620.6022 (6)0.3975 (3)0.6580 (2)0.0883 (11)
C720.6427 (4)0.4026 (2)0.57911 (19)0.0707 (8)
C820.6001 (3)0.32949 (19)0.53042 (16)0.0554 (7)
C920.6260 (4)0.3354 (2)0.45573 (18)0.0647 (8)
C1020.6970 (4)0.4132 (3)0.4293 (3)0.0870 (11)
C1120.7424 (5)0.4845 (3)0.4770 (3)0.1061 (14)
C1220.7145 (5)0.4807 (3)0.5503 (3)0.0960 (13)
H110.258 (3)0.0071 (17)0.4178 (13)0.052 (8)*
H210.313 (4)0.021 (2)0.5502 (16)0.090 (10)*
H910.124 (3)0.0127 (18)0.2939 (13)0.062 (8)*
H1010.013 (4)0.0585 (19)0.1789 (16)0.078 (10)*
H1110.129 (4)0.193 (2)0.1640 (19)0.088 (11)*
H1210.172 (4)0.298 (2)0.2650 (18)0.103 (11)*
H4110.061 (7)0.101 (3)0.647 (3)0.20 (2)*
H4210.242 (5)0.093 (3)0.654 (2)0.136 (18)*
H4310.144 (5)0.179 (3)0.635 (2)0.123 (17)*
H5110.009 (3)0.2741 (19)0.5158 (16)0.070 (9)*
H5210.149 (4)0.207 (2)0.4938 (17)0.097 (10)*
H6110.144 (4)0.316 (2)0.3957 (18)0.108 (12)*
H6210.045 (4)0.316 (2)0.4043 (16)0.090 (11)*
H120.448 (3)0.1653 (16)0.4767 (14)0.052 (7)*
H920.594 (3)0.2827 (18)0.4213 (14)0.064 (8)*
H1020.709 (4)0.420 (2)0.3768 (18)0.090 (11)*
H1120.792 (4)0.545 (3)0.4611 (18)0.105 (12)*
H1220.738 (4)0.523 (2)0.5841 (18)0.093 (12)*
H4120.471 (4)0.130 (2)0.753 (2)0.115 (14)*
H4220.538 (7)0.054 (4)0.727 (3)0.20 (3)*
H4320.345 (6)0.068 (3)0.714 (2)0.141 (18)*
H5120.563 (3)0.3009 (16)0.7378 (14)0.054 (7)*
H5220.743 (4)0.281 (2)0.7087 (16)0.089 (9)*
H6120.480 (4)0.416 (2)0.6583 (16)0.087 (10)*
H6220.674 (4)0.440 (2)0.6878 (16)0.087 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0797 (5)0.0711 (5)0.0473 (4)0.0027 (4)0.0002 (3)0.0086 (4)
N210.0580 (15)0.0569 (15)0.0452 (13)0.0029 (12)0.0019 (11)0.0013 (11)
N110.0530 (14)0.0543 (15)0.0526 (14)0.0006 (12)0.0059 (11)0.0065 (12)
C110.0392 (14)0.0489 (16)0.0618 (17)0.0050 (13)0.0040 (12)0.0005 (13)
C210.0422 (15)0.0496 (16)0.0699 (18)0.0069 (13)0.0043 (13)0.0066 (14)
C310.0461 (15)0.0581 (18)0.0603 (17)0.0098 (13)0.0110 (13)0.0097 (14)
C410.084 (3)0.094 (3)0.064 (2)0.006 (3)0.017 (2)0.019 (2)
C510.0493 (19)0.068 (2)0.098 (3)0.0016 (17)0.0031 (18)0.019 (2)
C610.068 (2)0.063 (2)0.112 (3)0.006 (2)0.013 (2)0.001 (2)
C710.0475 (17)0.063 (2)0.082 (2)0.0069 (15)0.0018 (15)0.0095 (17)
C810.0427 (15)0.0624 (18)0.0600 (17)0.0098 (14)0.0005 (12)0.0029 (15)
C910.0510 (18)0.081 (2)0.0598 (19)0.0003 (17)0.0062 (14)0.0103 (17)
C1010.064 (2)0.113 (3)0.062 (2)0.010 (2)0.0102 (17)0.006 (2)
C1110.068 (2)0.121 (4)0.073 (3)0.012 (2)0.009 (2)0.037 (3)
C1210.061 (2)0.079 (3)0.098 (3)0.0074 (19)0.0103 (19)0.024 (2)
N120.0542 (14)0.0567 (15)0.0420 (12)0.0034 (11)0.0008 (10)0.0015 (12)
N220.0557 (14)0.0599 (14)0.0468 (12)0.0031 (12)0.0052 (10)0.0039 (11)
C120.0444 (15)0.0537 (17)0.0500 (16)0.0059 (13)0.0016 (12)0.0072 (13)
C220.0465 (16)0.069 (2)0.0482 (16)0.0126 (14)0.0028 (12)0.0120 (14)
C320.0540 (16)0.068 (2)0.0468 (16)0.0138 (15)0.0055 (12)0.0016 (14)
C420.086 (3)0.106 (3)0.053 (2)0.016 (3)0.0128 (19)0.013 (2)
C520.072 (2)0.094 (3)0.0493 (18)0.0105 (19)0.0010 (16)0.0199 (17)
C620.090 (3)0.078 (3)0.092 (3)0.001 (2)0.011 (2)0.034 (2)
C720.0636 (19)0.060 (2)0.085 (2)0.0026 (16)0.0093 (16)0.0110 (17)
C820.0430 (15)0.0570 (18)0.0648 (18)0.0066 (14)0.0015 (13)0.0048 (15)
C920.0602 (19)0.062 (2)0.072 (2)0.0029 (16)0.0088 (15)0.0083 (18)
C1020.074 (2)0.088 (3)0.100 (3)0.007 (2)0.011 (2)0.024 (3)
C1120.088 (3)0.083 (3)0.143 (4)0.014 (2)0.007 (3)0.028 (3)
C1220.094 (3)0.062 (3)0.124 (4)0.008 (2)0.024 (3)0.010 (3)
Geometric parameters (Å, º) top
N11—N211.349 (3)C101—C1111.372 (5)
N11—C111.344 (3)C101—H1010.93 (3)
N21—C311.337 (3)C111—C1211.361 (5)
C11—C211.374 (3)C111—H1110.87 (3)
C21—C311.388 (4)C121—H1211.03 (3)
N12—N221.356 (3)N12—H120.94 (2)
N12—C121.344 (3)C12—C821.446 (4)
N22—C321.337 (3)C22—C521.496 (4)
C12—C221.379 (3)C32—C421.489 (4)
C22—C321.388 (4)C42—H4120.92 (4)
N21—H211.09 (3)C42—H4220.88 (6)
N11—H110.89 (2)C42—H4320.94 (4)
C11—C811.450 (3)C52—C621.523 (5)
C21—C511.493 (4)C52—H5120.96 (2)
C31—C411.490 (4)C52—H5221.09 (3)
C41—H4110.97 (5)C62—C721.504 (5)
C41—H4210.88 (4)C62—H6121.03 (3)
C41—H4310.86 (4)C62—H6220.97 (3)
C51—C611.519 (5)C72—C821.397 (4)
C51—H5110.91 (3)C72—C1221.400 (5)
C51—H5211.00 (3)C82—C921.395 (4)
C61—C711.503 (4)C92—C1021.375 (5)
C61—H6110.97 (4)C92—H921.00 (3)
C61—H6210.97 (3)C102—C1121.370 (6)
C71—C1211.397 (4)C102—H1020.97 (3)
C71—C811.403 (4)C112—C1221.371 (6)
C81—C911.386 (4)C112—H1121.02 (4)
C91—C1011.394 (4)C122—H1220.87 (3)
C91—H910.98 (3)
C31—N21—N11108.0 (2)C71—C121—H121115.7 (19)
C31—N21—H21130.2 (15)C12—N12—N22110.9 (2)
N11—N21—H21121.7 (15)C12—N12—H12125.5 (14)
C11—N11—N21109.5 (2)N22—N12—H12123.7 (14)
C11—N11—H11128.2 (16)C32—N22—N12106.2 (2)
N21—N11—H11122.2 (16)N12—C12—C22107.1 (2)
N11—C11—C21107.7 (2)N12—C12—C82127.9 (2)
N11—C11—C81127.2 (2)C22—C12—C82124.9 (3)
C21—C11—C81125.0 (3)C12—C22—C32105.8 (2)
C11—C21—C31106.3 (2)C12—C22—C52120.2 (3)
C11—C21—C51121.2 (3)C32—C22—C52133.9 (3)
C31—C21—C51132.4 (3)N22—C32—C22110.1 (2)
N21—C31—C21108.5 (2)N22—C32—C42120.0 (3)
N21—C31—C41121.2 (3)C22—C32—C42129.9 (3)
C21—C31—C41130.3 (3)C32—C42—H412107 (2)
C31—C41—H411112 (3)C32—C42—H422112 (3)
C31—C41—H421114 (3)H412—C42—H42296 (4)
H411—C41—H421106 (4)C32—C42—H432112 (2)
C31—C41—H431111 (3)H412—C42—H432106 (3)
H411—C41—H43194 (4)H422—C42—H432121 (4)
H421—C41—H431119 (4)C22—C52—C62109.3 (3)
C21—C51—C61111.0 (3)C22—C52—H512110.5 (15)
C21—C51—H511111.6 (17)C62—C52—H512110.0 (15)
C61—C51—H511108.1 (17)C22—C52—H522107.4 (15)
C21—C51—H521107.1 (18)C62—C52—H522112.9 (15)
C61—C51—H521113.5 (18)H512—C52—H522107 (2)
H511—C51—H521106 (2)C72—C62—C52115.2 (3)
C71—C61—C51116.5 (3)C72—C62—H612107.8 (16)
C71—C61—H611111 (2)C52—C62—H612105.1 (17)
C51—C61—H611112 (2)C72—C62—H622108.5 (17)
C71—C61—H621104.2 (18)C52—C62—H622109.1 (17)
C51—C61—H621108.0 (18)H612—C62—H622111 (2)
H611—C61—H621104 (3)C82—C72—C122117.5 (4)
C121—C71—C81117.7 (3)C82—C72—C62119.9 (3)
C121—C71—C61120.9 (3)C122—C72—C62122.6 (3)
C81—C71—C61121.3 (3)C92—C82—C72120.8 (3)
C91—C81—C71121.1 (3)C92—C82—C12123.5 (3)
C91—C81—C11123.5 (3)C72—C82—C12115.6 (3)
C71—C81—C11115.4 (3)C102—C92—C82120.1 (4)
C81—C91—C101119.3 (3)C102—C92—H92120.0 (15)
C81—C91—H91120.4 (14)C82—C92—H92119.9 (15)
C101—C91—H91120.2 (15)C112—C102—C92119.5 (4)
C111—C101—C91119.4 (4)C112—C102—H102119.3 (19)
C111—C101—H101125.5 (19)C92—C102—H102121.1 (19)
C91—C101—H101115.0 (19)C102—C112—C122121.2 (4)
C121—C111—C101121.5 (4)C102—C112—H112123.8 (19)
C121—C111—H111124 (2)C122—C112—H112115.0 (19)
C101—C111—H111114 (2)C112—C122—C72120.9 (4)
C111—C121—C71120.8 (4)C112—C122—H122127 (2)
C111—C121—H121123.5 (19)C72—C122—H122112 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···Cl3.081 (2)0.89 (2)2.20 (2)170 (2)
N21—H21···N222.714 (3)1.09 (3)1.63 (3)169 (3)
N12—H12···Cl3.101 (3)0.94 (2)2.17 (2)168 (2)
 
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