Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620005525/wp3004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005525/wp30041sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005525/wp30043sup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005525/wp30043sup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005525/wp30044sup10.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005525/wp30044sup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005525/wp30045sup11.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005525/wp30045sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005525/wp30046sup6.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005525/wp30049sup12.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005525/wp30049sup7.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005525/wp300410sup13.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005525/wp300410sup8.hkl |
CCDC references: 1998106; 1998105; 1998104; 1998103; 1998102; 1998101; 1998100
For all structures, data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C6H9N2O+·HF2− | F(000) = 172 |
Mr = 164.16 | Dx = 1.484 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9253 (16) Å | Cell parameters from 1096 reflections |
b = 5.9962 (14) Å | θ = 3.0–29.4° |
c = 8.433 (2) Å | µ = 0.14 mm−1 |
β = 113.551 (18)° | T = 120 K |
V = 367.39 (16) Å3 | Block, colourless |
Z = 2 | 0.25 × 0.04 × 0.04 mm |
Stoe IPDS 2T diffractometer | 1075 independent reflections |
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2 | 1009 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.028 |
Detector resolution: 6.67 pixels mm-1 | θmax = 29.3°, θmin = 4.3° |
rotation method scans | h = −10→10 |
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)] | k = −8→8 |
Tmin = 0.949, Tmax = 0.983 | l = −11→11 |
6035 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0471P)2 + 0.1674P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1075 reflections | Δρmax = 0.39 e Å−3 |
84 parameters | Δρmin = −0.32 e Å−3 |
1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.71017 (14) | 0.250000 | 0.91063 (13) | 0.0205 (2) | |
N2 | 0.72246 (15) | 0.250000 | 0.64423 (14) | 0.0140 (2) | |
H2 | 0.601583 | 0.250000 | 0.592192 | 0.017* | |
N6 | 0.99054 (14) | 0.250000 | 0.89619 (14) | 0.0137 (2) | |
H6 | 1.046662 | 0.250000 | 1.009730 | 0.016* | |
C1 | 0.80061 (17) | 0.250000 | 0.82331 (16) | 0.0140 (3) | |
C3 | 0.81877 (18) | 0.250000 | 0.54510 (16) | 0.0142 (3) | |
C4 | 1.00892 (18) | 0.250000 | 0.62426 (16) | 0.0155 (3) | |
H4 | 1.080338 | 0.250000 | 0.556716 | 0.019* | |
C5 | 1.09434 (17) | 0.250000 | 0.80387 (17) | 0.0142 (3) | |
C7 | 0.7107 (2) | 0.250000 | 0.35340 (17) | 0.0196 (3) | |
C8 | 1.29731 (18) | 0.250000 | 0.90421 (19) | 0.0192 (3) | |
F1 | 0.36129 (11) | 0.250000 | 0.50873 (11) | 0.0214 (2) | |
H1 | 0.255 (2) | 0.250000 | 0.3699 (12) | 0.064 (9)* | |
F2 | 0.13833 (15) | 0.250000 | 0.23660 (11) | 0.0316 (3) | |
H7A | 0.790 (3) | 0.250000 | 0.294 (3) | 0.030 (5)* | |
H8A | 1.362 (3) | 0.250000 | 0.827 (3) | 0.032 (6)* | |
H8B | 1.331 (2) | 0.120 (3) | 0.9768 (18) | 0.031 (4)* | |
H7B | 0.631 (2) | 0.121 (3) | 0.3222 (19) | 0.033 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0167 (5) | 0.0302 (6) | 0.0178 (5) | 0.000 | 0.0102 (4) | 0.000 |
N2 | 0.0121 (5) | 0.0156 (5) | 0.0135 (5) | 0.000 | 0.0044 (4) | 0.000 |
N6 | 0.0122 (5) | 0.0164 (5) | 0.0120 (4) | 0.000 | 0.0041 (4) | 0.000 |
C1 | 0.0134 (6) | 0.0147 (6) | 0.0144 (6) | 0.000 | 0.0059 (4) | 0.000 |
C3 | 0.0184 (6) | 0.0111 (5) | 0.0138 (5) | 0.000 | 0.0071 (5) | 0.000 |
C4 | 0.0172 (6) | 0.0159 (6) | 0.0164 (6) | 0.000 | 0.0100 (5) | 0.000 |
C5 | 0.0136 (5) | 0.0122 (5) | 0.0175 (6) | 0.000 | 0.0071 (5) | 0.000 |
C7 | 0.0244 (7) | 0.0204 (6) | 0.0122 (6) | 0.000 | 0.0055 (5) | 0.000 |
C8 | 0.0123 (6) | 0.0229 (7) | 0.0218 (6) | 0.000 | 0.0062 (5) | 0.000 |
F1 | 0.0143 (4) | 0.0300 (5) | 0.0168 (4) | 0.000 | 0.0029 (3) | 0.000 |
F2 | 0.0386 (6) | 0.0322 (5) | 0.0140 (4) | 0.000 | 0.0001 (4) | 0.000 |
O1—C1 | 1.2156 (16) | C4—C5 | 1.3904 (18) |
N2—H2 | 0.8800 | C5—C8 | 1.4886 (18) |
N2—C1 | 1.3846 (16) | C7—H7A | 0.95 (2) |
N2—C3 | 1.3385 (16) | C7—H7B | 0.967 (16) |
N6—H6 | 0.8800 | C7—H7Bi | 0.967 (16) |
N6—C1 | 1.3800 (16) | C8—H8A | 0.98 (2) |
N6—C5 | 1.3396 (16) | C8—H8B | 0.962 (16) |
C3—C4 | 1.3831 (18) | C8—H8Bi | 0.962 (16) |
C3—C7 | 1.4968 (18) | F1—H1 | 1.1360 (15) |
C4—H4 | 0.9500 | F2—H1 | 1.1360 (15) |
C1—N2—H2 | 117.9 | N6—C5—C4 | 119.24 (12) |
C3—N2—H2 | 117.9 | N6—C5—C8 | 116.40 (12) |
C3—N2—C1 | 124.28 (11) | C4—C5—C8 | 124.36 (12) |
C1—N6—H6 | 118.1 | C3—C7—H7A | 111.2 (13) |
C5—N6—H6 | 118.1 | C3—C7—H7B | 108.9 (9) |
C5—N6—C1 | 123.71 (11) | C3—C7—H7Bi | 108.9 (9) |
O1—C1—N2 | 123.07 (12) | H7A—C7—H7B | 110.5 (11) |
O1—C1—N6 | 122.18 (12) | H7A—C7—H7Bi | 110.5 (11) |
N6—C1—N2 | 114.75 (11) | H7B—C7—H7Bi | 106.7 (18) |
N2—C3—C4 | 118.80 (12) | C5—C8—H8A | 111.1 (13) |
N2—C3—C7 | 116.86 (12) | C5—C8—H8Bi | 109.1 (9) |
C4—C3—C7 | 124.34 (12) | C5—C8—H8B | 109.1 (9) |
C3—C4—H4 | 120.4 | H8A—C8—H8Bi | 109.5 (11) |
C3—C4—C5 | 119.22 (12) | H8A—C8—H8B | 109.5 (11) |
C5—C4—H4 | 120.4 | H8B—C8—H8Bi | 108.5 (17) |
Symmetry code: (i) x, −y+1/2, z. |
C6H9N2O+·Br− | Dx = 1.723 Mg m−3 |
Mr = 205.06 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pnma | Cell parameters from 16240 reflections |
a = 14.4984 (18) Å | θ = 3.8–29.7° |
b = 6.722 (2) Å | µ = 5.13 mm−1 |
c = 8.113 (7) Å | T = 120 K |
V = 790.6 (7) Å3 | Plate, colourless |
Z = 4 | 0.35 × 0.20 × 0.03 mm |
F(000) = 408 |
Stoe IPDS 2T diffractometer | 1130 independent reflections |
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2 | 971 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.050 |
Detector resolution: 6.67 pixels mm-1 | θmax = 29.0°, θmin = 3.8° |
rotation method scans | h = −19→19 |
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)] | k = −9→8 |
Tmin = 0.639, Tmax = 0.905 | l = −11→11 |
10482 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0666P)2 + 0.2083P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
1130 reflections | Δρmax = 0.74 e Å−3 |
75 parameters | Δρmin = −0.59 e Å−3 |
12 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.35196 (2) | 0.250000 | 0.50127 (2) | 0.02388 (16) | |
O1 | 0.58317 (14) | 0.250000 | 0.8135 (2) | 0.0371 (5) | |
N2 | 0.57782 (16) | 0.250000 | 0.5322 (3) | 0.0226 (4) | |
H2 | 0.517129 | 0.250000 | 0.532890 | 0.027* | |
N6 | 0.71848 (15) | 0.250000 | 0.6681 (3) | 0.0248 (4) | |
H6 | 0.751254 | 0.250000 | 0.759377 | 0.030* | |
C3 | 0.6210 (2) | 0.250000 | 0.3855 (3) | 0.0245 (5) | |
C5 | 0.7641 (2) | 0.250000 | 0.5243 (3) | 0.0242 (5) | |
C4 | 0.71538 (19) | 0.250000 | 0.3791 (3) | 0.0254 (5) | |
H4 | 0.746603 | 0.250000 | 0.276126 | 0.031* | |
C1 | 0.62334 (19) | 0.250000 | 0.6826 (3) | 0.0266 (5) | |
C7 | 0.5611 (2) | 0.250000 | 0.2362 (3) | 0.0326 (6) | |
C8 | 0.8668 (2) | 0.250000 | 0.5294 (4) | 0.0360 (7) | |
H7A | 0.5971 (13) | 0.250000 | 0.1340 (16) | 0.049 (12)* | |
H7B | 0.5221 (2) | 0.13098 (8) | 0.2398 (17) | 0.068 (8)* | |
H8A | 0.8902 (18) | 0.250000 | 0.6427 (11) | 0.057 (11)* | |
H8B | 0.8890 (9) | 0.13099 (8) | 0.4719 (10) | 0.054 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0223 (2) | 0.0298 (2) | 0.0195 (2) | 0.000 | −0.00044 (6) | 0.000 |
O1 | 0.0251 (9) | 0.0693 (15) | 0.0169 (9) | 0.000 | 0.0028 (7) | 0.000 |
N2 | 0.0199 (10) | 0.0304 (11) | 0.0176 (7) | 0.000 | 0.0006 (8) | 0.000 |
N6 | 0.0217 (9) | 0.0374 (12) | 0.0151 (8) | 0.000 | −0.0005 (7) | 0.000 |
C3 | 0.0306 (13) | 0.0276 (12) | 0.0152 (10) | 0.000 | 0.0005 (10) | 0.000 |
C5 | 0.0230 (13) | 0.0293 (12) | 0.0204 (9) | 0.000 | 0.0048 (9) | 0.000 |
C4 | 0.0272 (12) | 0.0328 (13) | 0.0163 (10) | 0.000 | 0.0024 (9) | 0.000 |
C1 | 0.0243 (11) | 0.0367 (14) | 0.0188 (11) | 0.000 | −0.0009 (10) | 0.000 |
C7 | 0.0327 (14) | 0.0472 (16) | 0.0179 (11) | 0.000 | −0.0034 (10) | 0.000 |
C8 | 0.0241 (12) | 0.057 (2) | 0.0273 (11) | 0.000 | 0.0020 (12) | 0.000 |
O1—C1 | 1.211 (3) | C5—C4 | 1.373 (4) |
N2—H2 | 0.8800 | C5—C8 | 1.490 (4) |
N2—C3 | 1.345 (3) | C4—H4 | 0.9500 |
N2—C1 | 1.387 (3) | C7—H7A | 0.9799 (12) |
N6—H6 | 0.8800 | C7—H7Bi | 0.9800 (8) |
N6—C5 | 1.340 (3) | C7—H7B | 0.9800 (8) |
N6—C1 | 1.384 (3) | C8—H8A | 0.9802 (12) |
C3—C4 | 1.369 (3) | C8—H8Bi | 0.9802 (8) |
C3—C7 | 1.490 (4) | C8—H8B | 0.9802 (8) |
C3—N2—H2 | 118.1 | O1—C1—N2 | 122.8 (3) |
C3—N2—C1 | 123.9 (2) | O1—C1—N6 | 123.6 (3) |
C1—N2—H2 | 118.1 | N6—C1—N2 | 113.5 (2) |
C5—N6—H6 | 117.8 | C3—C7—H7A | 112.1 (14) |
C5—N6—C1 | 124.4 (2) | C3—C7—H7B | 108.2 (7) |
C1—N6—H6 | 117.8 | C3—C7—H7Bi | 108.2 (7) |
N2—C3—C4 | 119.9 (2) | H7A—C7—H7B | 109.44 (13) |
N2—C3—C7 | 116.6 (3) | H7A—C7—H7Bi | 109.44 (13) |
C4—C3—C7 | 123.5 (2) | H7B—C7—H7Bi | 109.43 (16) |
N6—C5—C4 | 119.5 (3) | C5—C8—H8A | 111.8 (16) |
N6—C5—C8 | 118.0 (3) | C5—C8—H8Bi | 108.4 (8) |
C4—C5—C8 | 122.5 (2) | C5—C8—H8B | 108.4 (8) |
C3—C4—C5 | 118.8 (2) | H8A—C8—H8Bi | 109.39 (13) |
C3—C4—H4 | 120.6 | H8A—C8—H8B | 109.39 (13) |
C5—C4—H4 | 120.6 | H8B—C8—H8Bi | 109.40 (16) |
Symmetry code: (i) x, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Br1 | 0.88 | 2.41 | 3.284 (2) | 174 |
N6—H6···Br1ii | 0.88 | 2.43 | 3.308 (3) | 176 |
Symmetry code: (ii) x+1/2, y, −z+3/2. |
C6H9N2O+·I− | F(000) = 240 |
Mr = 252.05 | Dx = 1.899 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1803 (10) Å | Cell parameters from 1779 reflections |
b = 7.2139 (18) Å | θ = 3.4–27.7° |
c = 8.6574 (12) Å | µ = 3.57 mm−1 |
β = 100.603 (11)° | T = 120 K |
V = 440.78 (14) Å3 | Needles, colourless |
Z = 2 | 0.66 × 0.37 × 0.14 mm |
Stoe IPDS 2T diffractometer | 1166 independent reflections |
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2 | 1143 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.066 |
Detector resolution: 6.67 pixels mm-1 | θmax = 29.0°, θmin = 3.4° |
rotation method scans | h = −9→9 |
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)] | k = −9→9 |
Tmin = 0.274, Tmax = 0.624 | l = −10→11 |
5622 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.165 | w = 1/[σ2(Fo2) + (0.0966P)2 + 2.7212P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1166 reflections | Δρmax = 1.55 e Å−3 |
49 parameters | Δρmin = −1.29 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.250000 | 0.36113 (8) | 0.750000 | 0.0398 (3) | |
C1 | 0.250000 | 0.4775 (14) | 0.250000 | 0.0394 (19) | |
C3 | 0.2593 (9) | 0.7723 (10) | 0.3881 (9) | 0.0394 (13) | |
N2 | 0.2632 (9) | 0.5837 (9) | 0.3837 (7) | 0.0411 (12) | |
H2 | 0.275074 | 0.524688 | 0.473976 | 0.049* | |
C7 | 0.2664 (18) | 0.8639 (11) | 0.5416 (12) | 0.056 (2) | |
H7A | 0.143381 | 0.851002 | 0.574207 | 0.085* | |
H7B | 0.295644 | 0.995667 | 0.532394 | 0.085* | |
H7C | 0.364872 | 0.805749 | 0.620039 | 0.085* | |
O1 | 0.250000 | 0.3089 (13) | 0.250000 | 0.058 (2) | |
C4 | 0.250000 | 0.8710 (12) | 0.250000 | 0.041 (2) | |
H4 | 0.249999 | 1.002703 | 0.250000 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0384 (4) | 0.0395 (4) | 0.0419 (4) | 0.000 | 0.0083 (2) | 0.000 |
C1 | 0.038 (4) | 0.031 (4) | 0.048 (5) | 0.000 | 0.006 (4) | 0.000 |
C3 | 0.034 (3) | 0.033 (3) | 0.049 (3) | −0.003 (2) | 0.003 (2) | 0.003 (3) |
N2 | 0.042 (3) | 0.042 (3) | 0.039 (3) | 0.006 (2) | 0.005 (2) | 0.001 (2) |
C7 | 0.074 (6) | 0.045 (5) | 0.050 (5) | −0.006 (3) | 0.008 (4) | −0.003 (3) |
O1 | 0.089 (7) | 0.033 (4) | 0.056 (5) | 0.000 | 0.021 (4) | 0.000 |
C4 | 0.042 (5) | 0.025 (4) | 0.053 (6) | 0.000 | 0.004 (4) | 0.000 |
C1—N2 | 1.377 (8) | N2—H2 | 0.8800 |
C1—N2i | 1.377 (8) | C7—H7A | 0.9800 |
C1—O1 | 1.216 (14) | C7—H7B | 0.9800 |
C3—N2 | 1.362 (9) | C7—H7C | 0.9800 |
C3—C7 | 1.477 (12) | C4—H4 | 0.9500 |
C3—C4 | 1.382 (8) | ||
N2i—C1—N2 | 112.4 (9) | C3—C7—H7A | 109.5 |
O1—C1—N2i | 123.8 (4) | C3—C7—H7B | 109.5 |
O1—C1—N2 | 123.8 (4) | C3—C7—H7C | 109.5 |
N2—C3—C7 | 118.3 (7) | H7A—C7—H7B | 109.5 |
N2—C3—C4 | 119.3 (7) | H7A—C7—H7C | 109.5 |
C4—C3—C7 | 122.4 (7) | H7B—C7—H7C | 109.5 |
C1—N2—H2 | 117.3 | C3i—C4—C3 | 118.0 (9) |
C3—N2—C1 | 125.5 (7) | C3—C4—H4 | 121.0 |
C3—N2—H2 | 117.3 | C3i—C4—H4 | 121.0 |
Symmetry code: (i) −x+1/2, y, −z+1/2. |
C6H9N2O+·I−·CH4N2O | F(000) = 608 |
Mr = 312.11 | Dx = 1.829 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.772 (1) Å | Cell parameters from 3188 reflections |
b = 11.5579 (10) Å | θ = 3.0–29.4° |
c = 14.0700 (16) Å | µ = 2.81 mm−1 |
β = 127.378 (7)° | T = 120 K |
V = 1133.6 (2) Å3 | Prism, colourless |
Z = 4 | 0.49 × 0.42 × 0.19 mm |
Stoe IPDS 2T diffractometer | 2995 independent reflections |
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2 | 2800 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.050 |
Detector resolution: 6.67 pixels mm-1 | θmax = 29.0°, θmin = 3.4° |
rotation method scans | h = −11→11 |
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)] | k = −15→15 |
Tmin = 0.258, Tmax = 0.579 | l = −19→19 |
16324 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.061P)2 + 0.6546P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
2995 reflections | Δρmax = 0.84 e Å−3 |
129 parameters | Δρmin = −1.25 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.83377 (2) | 0.74469 (2) | 0.35562 (2) | 0.02789 (9) | |
O1U | 0.5613 (2) | 0.14468 (14) | 0.46992 (15) | 0.0333 (3) | |
O1 | 0.6489 (3) | 0.44215 (14) | 0.44055 (16) | 0.0342 (4) | |
N2 | 0.7967 (3) | 0.44561 (16) | 0.35149 (17) | 0.0288 (4) | |
H2 | 0.809381 | 0.521263 | 0.359539 | 0.035* | |
N6 | 0.6879 (3) | 0.27280 (16) | 0.37324 (18) | 0.0269 (4) | |
H6 | 0.627973 | 0.233371 | 0.395104 | 0.032* | |
N1U | 0.4346 (3) | 0.29408 (18) | 0.5062 (2) | 0.0337 (4) | |
H1UA | 0.485102 | 0.345600 | 0.486678 | 0.040* | |
H1UB | 0.365183 | 0.316836 | 0.528741 | 0.040* | |
C1 | 0.7072 (3) | 0.39069 (18) | 0.39252 (19) | 0.0274 (4) | |
C5 | 0.7551 (3) | 0.21480 (19) | 0.32306 (19) | 0.0279 (4) | |
C3 | 0.8663 (3) | 0.39169 (18) | 0.29974 (19) | 0.0281 (4) | |
C1U | 0.4631 (4) | 0.1814 (2) | 0.5016 (2) | 0.0303 (5) | |
N2U | 0.3831 (3) | 0.10581 (18) | 0.5326 (2) | 0.0411 (5) | |
H2UA | 0.399411 | 0.030962 | 0.530629 | 0.049* | |
H2UB | 0.314446 | 0.131331 | 0.554735 | 0.049* | |
C4 | 0.8454 (4) | 0.2744 (2) | 0.2849 (2) | 0.0297 (4) | |
H4 | 0.892487 | 0.234216 | 0.248637 | 0.036* | |
C8 | 0.7286 (4) | 0.08672 (19) | 0.3136 (2) | 0.0347 (5) | |
H8A | 0.844970 | 0.049635 | 0.382072 | 0.052* | |
H8B | 0.703908 | 0.059710 | 0.239327 | 0.052* | |
H8C | 0.619515 | 0.066691 | 0.313008 | 0.052* | |
C7 | 0.9637 (4) | 0.4651 (2) | 0.2641 (2) | 0.0354 (5) | |
H7A | 0.877315 | 0.527494 | 0.211581 | 0.053* | |
H7B | 0.997284 | 0.417626 | 0.221505 | 0.053* | |
H7C | 1.080603 | 0.498420 | 0.335673 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.03397 (14) | 0.01755 (12) | 0.03683 (14) | 0.00064 (4) | 0.02392 (11) | 0.00024 (4) |
O1U | 0.0442 (9) | 0.0230 (8) | 0.0462 (9) | 0.0034 (6) | 0.0344 (8) | 0.0025 (6) |
O1 | 0.0461 (9) | 0.0230 (8) | 0.0480 (9) | 0.0021 (6) | 0.0360 (8) | −0.0009 (6) |
N2 | 0.0394 (9) | 0.0168 (8) | 0.0387 (10) | 0.0001 (7) | 0.0282 (8) | −0.0003 (6) |
N6 | 0.0320 (9) | 0.0184 (7) | 0.0359 (9) | −0.0007 (7) | 0.0235 (8) | 0.0006 (7) |
N1U | 0.0496 (12) | 0.0185 (9) | 0.0459 (11) | 0.0028 (8) | 0.0358 (10) | 0.0011 (8) |
C1 | 0.0304 (9) | 0.0197 (9) | 0.0350 (10) | 0.0006 (7) | 0.0215 (8) | 0.0004 (7) |
C5 | 0.0337 (10) | 0.0193 (9) | 0.0329 (10) | 0.0011 (8) | 0.0214 (9) | −0.0012 (8) |
C3 | 0.0335 (10) | 0.0221 (10) | 0.0328 (10) | 0.0011 (7) | 0.0223 (8) | −0.0001 (7) |
C1U | 0.0362 (11) | 0.0247 (11) | 0.0363 (11) | 0.0012 (8) | 0.0253 (9) | 0.0013 (8) |
N2U | 0.0621 (14) | 0.0225 (9) | 0.0674 (14) | −0.0010 (9) | 0.0542 (12) | −0.0022 (9) |
C4 | 0.0385 (12) | 0.0209 (9) | 0.0370 (11) | 0.0014 (9) | 0.0267 (10) | −0.0025 (9) |
C8 | 0.0476 (13) | 0.0187 (10) | 0.0486 (13) | −0.0008 (9) | 0.0348 (11) | −0.0020 (8) |
C7 | 0.0512 (13) | 0.0225 (10) | 0.0482 (12) | −0.0027 (9) | 0.0382 (11) | −0.0019 (9) |
O1U—C1U | 1.260 (3) | C3—C4 | 1.367 (3) |
O1—C1 | 1.221 (3) | C3—C7 | 1.491 (3) |
N2—H2 | 0.8800 | C1U—N2U | 1.348 (3) |
N2—C1 | 1.379 (3) | N2U—H2UA | 0.8800 |
N2—C3 | 1.353 (3) | N2U—H2UB | 0.8800 |
N6—H6 | 0.8800 | C4—H4 | 0.9500 |
N6—C1 | 1.379 (3) | C8—H8A | 0.9800 |
N6—C5 | 1.342 (3) | C8—H8B | 0.9800 |
N1U—H1UA | 0.8800 | C8—H8C | 0.9800 |
N1U—H1UB | 0.8800 | C7—H7A | 0.9800 |
N1U—C1U | 1.336 (3) | C7—H7B | 0.9800 |
C5—C4 | 1.381 (3) | C7—H7C | 0.9800 |
C5—C8 | 1.492 (3) | ||
C1—N2—H2 | 117.6 | N1U—C1U—N2U | 117.8 (2) |
C3—N2—H2 | 117.6 | C1U—N2U—H2UA | 120.0 |
C3—N2—C1 | 124.78 (19) | C1U—N2U—H2UB | 120.0 |
C1—N6—H6 | 118.1 | H2UA—N2U—H2UB | 120.0 |
C5—N6—H6 | 118.1 | C5—C4—H4 | 120.3 |
C5—N6—C1 | 123.8 (2) | C3—C4—C5 | 119.4 (2) |
H1UA—N1U—H1UB | 120.0 | C3—C4—H4 | 120.3 |
C1U—N1U—H1UA | 120.0 | C5—C8—H8A | 109.5 |
C1U—N1U—H1UB | 120.0 | C5—C8—H8B | 109.5 |
O1—C1—N2 | 122.90 (19) | C5—C8—H8C | 109.5 |
O1—C1—N6 | 123.1 (2) | H8A—C8—H8B | 109.5 |
N2—C1—N6 | 113.95 (18) | H8A—C8—H8C | 109.5 |
N6—C5—C4 | 119.6 (2) | H8B—C8—H8C | 109.5 |
N6—C5—C8 | 116.7 (2) | C3—C7—H7A | 109.5 |
C4—C5—C8 | 123.7 (2) | C3—C7—H7B | 109.5 |
N2—C3—C4 | 118.4 (2) | C3—C7—H7C | 109.5 |
N2—C3—C7 | 117.21 (19) | H7A—C7—H7B | 109.5 |
C4—C3—C7 | 124.4 (2) | H7A—C7—H7C | 109.5 |
O1U—C1U—N1U | 122.3 (2) | H7B—C7—H7C | 109.5 |
O1U—C1U—N2U | 119.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···I1 | 0.88 | 2.59 | 3.4692 (19) | 173 |
N6—H6···O1U | 0.88 | 1.80 | 2.666 (3) | 167 |
N1U—H1UA···O1 | 0.88 | 2.21 | 3.070 (3) | 167 |
N1U—H1UB···I1i | 0.88 | 3.11 | 3.883 (2) | 148 |
N2U—H2UA···O1Uii | 0.88 | 2.06 | 2.940 (3) | 179 |
N2U—H2UB···I1i | 0.88 | 2.71 | 3.565 (2) | 166 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
C6H9N2S+·F2H−·CH4N2S | F(000) = 268 |
Mr = 256.34 | Dx = 1.457 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
a = 6.3876 (11) Å | Cell parameters from 1229 reflections |
b = 8.8268 (13) Å | θ = 3.1–28.7° |
c = 10.500 (2) Å | µ = 0.46 mm−1 |
β = 99.355 (15)° | T = 120 K |
V = 584.15 (17) Å3 | Plate, yellow |
Z = 2 | 0.32 × 0.2 × 0.07 mm |
Stoe IPDS 2T diffractometer | 1532 independent reflections |
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2 | 1375 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.047 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.4°, θmin = 3.9° |
rotation method scans | h = −7→8 |
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)] | k = −10→11 |
Tmin = 0.853, Tmax = 0.967 | l = −13→13 |
3316 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.220 | w = 1/[σ2(Fo2) + (0.0998P)2 + 1.0253P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max < 0.001 |
1532 reflections | Δρmax = 0.55 e Å−3 |
80 parameters | Δρmin = −0.49 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1T | 0.5456 (2) | 0.750000 | 1.04796 (11) | 0.0367 (4) | |
S1 | 0.3578 (2) | 0.250000 | 0.63525 (12) | 0.0424 (4) | |
F1 | 0.2389 (4) | 0.6231 (2) | 0.5513 (2) | 0.0494 (6) | |
N1T | 0.4051 (4) | 0.6196 (3) | 0.8226 (3) | 0.0321 (6) | |
H1TA | 0.355387 | 0.620829 | 0.739409 | 0.038* | |
H1TB | 0.429412 | 0.532580 | 0.863319 | 0.038* | |
N2 | 0.2256 (4) | 0.3803 (3) | 0.4084 (3) | 0.0343 (6) | |
H2 | 0.252236 | 0.466934 | 0.449253 | 0.041* | |
C1T | 0.4438 (6) | 0.750000 | 0.8874 (4) | 0.0281 (8) | |
C4 | 0.1035 (6) | 0.250000 | 0.2147 (4) | 0.0299 (9) | |
H4 | 0.046347 | 0.250000 | 0.125352 | 0.036* | |
C3 | 0.1457 (5) | 0.3849 (4) | 0.2805 (3) | 0.0312 (7) | |
C7 | 0.1049 (5) | 0.5375 (4) | 0.2222 (4) | 0.0377 (7) | |
H7A | −0.001766 | 0.589839 | 0.263414 | 0.056* | |
H7B | 0.052706 | 0.527184 | 0.129569 | 0.056* | |
H7C | 0.236850 | 0.596255 | 0.235186 | 0.056* | |
C1 | 0.2672 (7) | 0.250000 | 0.4777 (5) | 0.0357 (10) | |
H1 | 0.261 (15) | 0.750000 | 0.545 (8) | 0.08 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1T | 0.0486 (7) | 0.0226 (6) | 0.0379 (6) | 0.000 | 0.0044 (5) | 0.000 |
S1 | 0.0433 (7) | 0.0448 (8) | 0.0376 (6) | 0.000 | 0.0023 (5) | 0.000 |
F1 | 0.0736 (16) | 0.0302 (11) | 0.0444 (12) | −0.0082 (11) | 0.0092 (10) | −0.0031 (9) |
N1T | 0.0333 (13) | 0.0207 (12) | 0.0411 (14) | −0.0006 (10) | 0.0031 (10) | −0.0007 (10) |
N2 | 0.0333 (13) | 0.0276 (14) | 0.0421 (14) | −0.0011 (10) | 0.0066 (11) | −0.0023 (10) |
C1T | 0.0260 (18) | 0.0223 (19) | 0.035 (2) | 0.000 | 0.0037 (15) | 0.000 |
C4 | 0.0264 (18) | 0.024 (2) | 0.039 (2) | 0.000 | 0.0062 (16) | 0.000 |
C3 | 0.0273 (13) | 0.0259 (15) | 0.0414 (16) | −0.0020 (11) | 0.0083 (11) | 0.0001 (11) |
C7 | 0.0381 (16) | 0.0232 (15) | 0.0515 (19) | −0.0008 (12) | 0.0068 (13) | 0.0017 (13) |
C1 | 0.033 (2) | 0.036 (2) | 0.038 (2) | 0.000 | 0.0056 (17) | 0.000 |
S1T—C1T | 1.706 (4) | N2—C1 | 1.363 (4) |
S1—C1 | 1.662 (5) | C4—H4 | 0.9500 |
F1—H1 | 1.132 (14) | C4—C3i | 1.381 (4) |
N1T—H1TA | 0.8800 | C4—C3 | 1.381 (4) |
N1T—H1TB | 0.8800 | C3—C7 | 1.485 (4) |
N1T—C1T | 1.340 (3) | C7—H7A | 0.9800 |
N2—H2 | 0.8800 | C7—H7B | 0.9800 |
N2—C3 | 1.357 (4) | C7—H7C | 0.9800 |
H1TA—N1T—H1TB | 120.0 | N2—C3—C4 | 118.7 (3) |
C1T—N1T—H1TA | 120.0 | N2—C3—C7 | 116.6 (3) |
C1T—N1T—H1TB | 120.0 | C4—C3—C7 | 124.7 (3) |
C3—N2—H2 | 117.9 | C3—C7—H7A | 109.5 |
C3—N2—C1 | 124.2 (3) | C3—C7—H7B | 109.5 |
C1—N2—H2 | 117.9 | C3—C7—H7C | 109.5 |
N1T—C1T—S1T | 120.7 (2) | H7A—C7—H7B | 109.5 |
N1Tii—C1T—S1T | 120.7 (2) | H7A—C7—H7C | 109.5 |
N1Tii—C1T—N1T | 118.5 (4) | H7B—C7—H7C | 109.5 |
C3i—C4—H4 | 120.4 | N2i—C1—S1 | 122.5 (2) |
C3—C4—H4 | 120.4 | N2—C1—S1 | 122.5 (2) |
C3i—C4—C3 | 119.1 (4) | N2—C1—N2i | 115.0 (4) |
Symmetry codes: (i) x, −y+1/2, z; (ii) x, −y+3/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1T—H1TA···F1 | 0.88 | 1.99 | 2.874 (4) | 179 |
N1T—H1TB···S1Tiii | 0.88 | 2.66 | 3.528 (3) | 170 |
N2—H2···F1 | 0.88 | 1.76 | 2.610 (4) | 163 |
Symmetry code: (iii) −x+1, −y+1, −z+2. |
C6H9N2S+·Br− | F(000) = 440 |
Mr = 221.12 | Dx = 1.725 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4675 (11) Å | Cell parameters from 2102 reflections |
b = 14.9142 (19) Å | θ = 3.8–28.8° |
c = 6.8814 (9) Å | µ = 5.02 mm−1 |
β = 101.575 (10)° | T = 120 K |
V = 851.35 (19) Å3 | Prism, yellow |
Z = 4 | 0.21 × 0.14 × 0.04 mm |
Stoe IPDS 2T diffractometer | 933 independent reflections |
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2 | 871 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.118 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.0°, θmin = 3.8° |
rotation method scans | h = −10→10 |
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)] | k = −18→18 |
Tmin = 0.262, Tmax = 0.740 | l = −8→8 |
5070 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.168 | w = 1/[σ2(Fo2) + (0.1393P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
933 reflections | Δρmax = 2.21 e Å−3 |
49 parameters | Δρmin = −1.62 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.000000 | 0.19294 (3) | 0.250000 | 0.0325 (3) | |
S1 | 0.500000 | 0.12830 (11) | 0.250000 | 0.0368 (5) | |
N2 | 0.3645 (5) | 0.2889 (2) | 0.2528 (6) | 0.0310 (8) | |
H2 | 0.273349 | 0.259950 | 0.248504 | 0.037* | |
C1 | 0.500000 | 0.2400 (4) | 0.250000 | 0.0296 (12) | |
C3 | 0.3622 (5) | 0.3795 (3) | 0.2619 (5) | 0.0307 (8) | |
C4 | 0.500000 | 0.4264 (4) | 0.250000 | 0.0327 (12) | |
H4 | 0.500001 | 0.490054 | 0.249997 | 0.039* | |
C7 | 0.2091 (6) | 0.4223 (3) | 0.2835 (7) | 0.0381 (9) | |
H7A | 0.126072 | 0.410019 | 0.165295 | 0.057* | |
H7B | 0.224963 | 0.487166 | 0.298873 | 0.057* | |
H7C | 0.174921 | 0.397957 | 0.400812 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0298 (5) | 0.0429 (5) | 0.0265 (5) | 0.000 | 0.0095 (3) | 0.000 |
S1 | 0.0363 (8) | 0.0359 (9) | 0.0419 (9) | 0.000 | 0.0168 (7) | 0.000 |
N2 | 0.0274 (17) | 0.0390 (16) | 0.0292 (19) | 0.0001 (15) | 0.0117 (15) | 0.0000 (14) |
C1 | 0.026 (2) | 0.033 (3) | 0.032 (3) | 0.000 | 0.011 (2) | 0.000 |
C3 | 0.0262 (17) | 0.041 (2) | 0.0255 (18) | 0.0037 (16) | 0.0081 (14) | −0.0010 (15) |
C4 | 0.035 (3) | 0.039 (3) | 0.025 (3) | 0.000 | 0.008 (2) | 0.000 |
C7 | 0.031 (2) | 0.046 (2) | 0.039 (2) | 0.0046 (17) | 0.0114 (19) | −0.0009 (17) |
S1—C1 | 1.665 (6) | C3—C7 | 1.479 (6) |
N2—H2 | 0.8800 | C4—H4 | 0.9500 |
N2—C1 | 1.363 (5) | C7—H7A | 0.9800 |
N2—C3 | 1.352 (5) | C7—H7B | 0.9800 |
C3—C4 | 1.377 (5) | C7—H7C | 0.9800 |
C1—N2—H2 | 118.1 | C3i—C4—C3 | 119.0 (6) |
C3—N2—H2 | 118.1 | C3—C4—H4 | 120.5 |
C3—N2—C1 | 123.8 (4) | C3i—C4—H4 | 120.5 |
N2—C1—S1 | 122.4 (3) | C3—C7—H7A | 109.5 |
N2i—C1—S1 | 122.4 (3) | C3—C7—H7B | 109.5 |
N2—C1—N2i | 115.2 (5) | C3—C7—H7C | 109.5 |
N2—C3—C4 | 118.9 (4) | H7A—C7—H7B | 109.5 |
N2—C3—C7 | 117.2 (4) | H7A—C7—H7C | 109.5 |
C4—C3—C7 | 123.9 (4) | H7B—C7—H7C | 109.5 |
Symmetry code: (i) −x+1, y, −z+1/2. |
C6H9N2S+·I− | Dx = 1.913 Mg m−3 |
Mr = 268.11 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Cmcm | Cell parameters from 1294 reflections |
a = 8.7198 (14) Å | θ = 3.9–26.7° |
b = 15.095 (3) Å | µ = 3.60 mm−1 |
c = 7.0716 (11) Å | T = 120 K |
V = 930.8 (3) Å3 | Plate, yellow |
Z = 4 | 0.17 × 0.12 × 0.05 mm |
F(000) = 512 |
Stoe IPDS 2T diffractometer | 708 independent reflections |
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2 | 661 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.058 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.9°, θmin = 4.0° |
rotation method scans | h = −11→11 |
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)] | k = −20→20 |
Tmin = 0.520, Tmax = 0.837 | l = −9→9 |
7434 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.025 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.060 | w = 1/[σ2(Fo2) + (0.0431P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
708 reflections | Δρmax = 1.10 e Å−3 |
42 parameters | Δρmin = −0.88 e Å−3 |
6 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.000000 | 0.18528 (2) | 0.750000 | 0.02004 (12) | |
S1 | 0.500000 | 0.12787 (8) | 0.750000 | 0.0258 (3) | |
N2 | 0.3682 (3) | 0.28725 (19) | 0.750000 | 0.0195 (6) | |
H2 | 0.280127 | 0.258795 | 0.750000 | 0.023* | |
C1 | 0.500000 | 0.2378 (3) | 0.750000 | 0.0198 (9) | |
C4 | 0.500000 | 0.4226 (3) | 0.750000 | 0.0201 (9) | |
H4 | 0.499999 | 0.485535 | 0.750000 | 0.024* | |
C3 | 0.3643 (4) | 0.3766 (2) | 0.750000 | 0.0201 (6) | |
C7 | 0.2109 (5) | 0.4189 (2) | 0.750000 | 0.0298 (8) | |
H7A | 0.220 (4) | 0.4836 (3) | 0.750000 | 0.062 (18)* | |
H7B | 0.1549 (12) | 0.3999 (11) | 0.63687 (7) | 0.049 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01939 (17) | 0.01578 (17) | 0.02494 (19) | 0.000 | 0.000 | 0.000 |
S1 | 0.0231 (6) | 0.0113 (5) | 0.0429 (8) | 0.000 | 0.000 | 0.000 |
N2 | 0.0177 (12) | 0.0140 (12) | 0.0267 (15) | −0.0014 (10) | 0.000 | 0.000 |
C1 | 0.021 (2) | 0.015 (2) | 0.024 (2) | 0.000 | 0.000 | 0.000 |
C4 | 0.020 (2) | 0.014 (2) | 0.026 (3) | 0.000 | 0.000 | 0.000 |
C3 | 0.0229 (15) | 0.0128 (14) | 0.0246 (17) | 0.0039 (12) | 0.000 | 0.000 |
C7 | 0.0262 (17) | 0.0175 (15) | 0.046 (3) | 0.0071 (13) | 0.000 | 0.000 |
S1—C1 | 1.659 (5) | C4—C3i | 1.372 (4) |
N2—H2 | 0.8800 | C3—C7 | 1.482 (5) |
N2—C1 | 1.371 (4) | C7—H7A | 0.9800 (11) |
N2—C3 | 1.350 (4) | C7—H7B | 0.9800 (7) |
C4—H4 | 0.9500 | C7—H7Bii | 0.9800 (7) |
C4—C3 | 1.372 (4) | ||
C1—N2—H2 | 117.8 | N2—C3—C4 | 118.9 (3) |
C3—N2—H2 | 117.8 | N2—C3—C7 | 117.0 (3) |
C3—N2—C1 | 124.5 (3) | C4—C3—C7 | 124.1 (3) |
N2i—C1—S1 | 123.0 (2) | C3—C7—H7A | 111 (2) |
N2—C1—S1 | 123.0 (2) | C3—C7—H7B | 108.9 (10) |
N2i—C1—N2 | 113.9 (4) | C3—C7—H7Bii | 108.9 (10) |
C3—C4—H4 | 120.4 | H7A—C7—H7B | 109.43 (13) |
C3i—C4—H4 | 120.4 | H7A—C7—H7Bii | 109.43 (13) |
C3—C4—C3i | 119.2 (4) | H7B—C7—H7Bii | 109.43 (16) |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, y, −z+3/2. |
G | X- | Y | Reference | |
(1) | O | F2H- | - | This work |
(2) | O | Cl- | - | Lee et al. (1984) |
(3) | O | Br- | - | This work |
(4) | O | I- | - | This work |
(5) | O | I- | OC(NH2)2 | This work |
(6) | S | F2H- | SC(NH2)2 | This work |
(7) | S | Cl- | H2O | Battaglia et al. (1986) and Seth et al. (1996) |
(8) | S | Cl- | SC(NH2)2 | Gaye et al. (2009) |
(9) | S | Br- | - | This work |
(10) | S | I- | - | This work |
Compound | (1) | (2) | (3) | (4) | (5) | (6) | (8) | (9) | (10) |
X | F2H | Cl | Br | I | I | F2H | Cl | Br | I |
Distance X···p | 2.998 | 3.334 | 3.361 | 3.566 | 3.559, 3.632 | 3.188, 3.051 | 3.323 | 3.464 | 3.536 |
Distance X···d | 3.054 | 3.366 | 3.385 | 3.601 | 3.515, 3.530 | 3.828, 3.279 | 3.490 | 3.338 | 3.545 |
Type | a | a | a | b | c | d | d | a | a |
Symmetry | m on ring | m on ring | m on ring | 2 on I | 1 (none) | vertical m on F2H | m on ring & mm2 on Cl | 2 on Br | m on ring & mm2 on I |
RvdW(X) (Mantina et al., 2009) | 1.40 | 1.74 | 1.82 | 1.99 | 1.99 | 1.40 | 1.74 | 1.82 | 1.99 |
Plane proximity | 1.598 | 1.594 | 1.541 | 1.576 | 1.569, 1.642 | 1.788, 1.651 | 1.583 | 1.644 | 1.546 |
Shift | 0.582 | 0.463 | 0.402 | 0.501 | 0.558, 0.854 | 2.119, 1.201 | 1.067 | 0.926 | 0.252 |
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