Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622008464/zo3026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622008464/zo30266sup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622008464/zo30266sup8.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622008464/zo30267sup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622008464/zo30267sup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622008464/zo30267H2Osup10.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622008464/zo30267H2Osup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622008464/zo30268sup11.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622008464/zo30268sup5.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622008464/zo30269sup12.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622008464/zo30269sup6.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622008464/zo302610sup13.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622008464/zo302610sup7.hkl |
CCDC references: 2203085; 2203084; 2203083; 2203082; 2203081; 2203080
For all structures, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014 (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).
C8H16N3+·C7H7O3S− | F(000) = 696 |
Mr = 325.42 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1202 (3) Å | Cell parameters from 8847 reflections |
b = 25.213 (1) Å | θ = 2.6–37.7° |
c = 10.5669 (4) Å | µ = 0.22 mm−1 |
β = 106.403 (2)° | T = 100 K |
V = 1564.20 (12) Å3 | Plate, colourless |
Z = 4 | 0.33 × 0.19 × 0.05 mm |
Bruker D8 Quest PHOTON CCD detector diffractometer | 6080 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
ω scans | θmax = 37.9°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −10→10 |
Tmin = 0.590, Tmax = 0.747 | k = −42→43 |
39454 measured reflections | l = −17→18 |
8355 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0527P)2 + 0.4847P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.003 |
8355 reflections | Δρmax = 0.57 e Å−3 |
200 parameters | Δρmin = −0.58 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. |
Refinement. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H2O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F2. Non-hydrogen atoms were refined anisotropically. All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.54703 (4) | 0.61026 (2) | 0.54442 (3) | 0.01154 (6) | |
O1 | 0.60040 (16) | 0.56781 (3) | 0.46451 (9) | 0.01973 (17) | |
O2 | 0.30391 (14) | 0.61544 (3) | 0.52904 (9) | 0.01677 (15) | |
O3 | 0.68106 (15) | 0.60728 (3) | 0.68277 (8) | 0.01814 (16) | |
C9 | 0.62948 (17) | 0.66972 (4) | 0.48035 (10) | 0.01138 (16) | |
C10 | 0.85793 (18) | 0.68393 (4) | 0.51429 (11) | 0.01447 (18) | |
H10 | 0.968608 | 0.662672 | 0.573953 | 0.017* | |
C11 | 0.92371 (19) | 0.72948 (5) | 0.46040 (11) | 0.01600 (19) | |
H11 | 1.079648 | 0.739539 | 0.485620 | 0.019* | |
C12 | 0.7655 (2) | 0.76070 (4) | 0.37010 (11) | 0.01529 (19) | |
C13 | 0.53625 (19) | 0.74570 (4) | 0.33644 (11) | 0.01629 (19) | |
H13 | 0.425655 | 0.766489 | 0.275387 | 0.020* | |
C14 | 0.46835 (18) | 0.70059 (4) | 0.39148 (11) | 0.01473 (18) | |
H14 | 0.312043 | 0.690897 | 0.368354 | 0.018* | |
C15 | 0.8412 (2) | 0.80853 (5) | 0.30823 (13) | 0.0243 (3) | |
H15A | 0.985575 | 0.821692 | 0.366206 | 0.036* | |
H15B | 0.725248 | 0.836369 | 0.295539 | 0.036* | |
H15C | 0.862036 | 0.798670 | 0.222681 | 0.036* | |
N1 | 0.97057 (15) | 0.55048 (3) | 0.20392 (8) | 0.01080 (14) | |
N2 | 0.77566 (15) | 0.52136 (4) | 0.11896 (8) | 0.01160 (15) | |
N3 | 0.54622 (16) | 0.45251 (4) | 0.14997 (9) | 0.01406 (16) | |
H3A | 0.459498 | 0.455162 | 0.068154 | 0.017* | |
H3B | 0.515894 | 0.428443 | 0.202917 | 0.017* | |
C1 | 0.72355 (17) | 0.48497 (4) | 0.19371 (10) | 0.01120 (16) | |
C2 | 0.87632 (18) | 0.48223 (4) | 0.33227 (10) | 0.01319 (17) | |
H2A | 0.919098 | 0.445227 | 0.359661 | 0.016* | |
H2B | 0.805188 | 0.498907 | 0.395689 | 0.016* | |
C3 | 1.07882 (18) | 0.51394 (4) | 0.31840 (10) | 0.01422 (18) | |
H3C | 1.150452 | 0.534303 | 0.399633 | 0.017* | |
H3D | 1.194512 | 0.490660 | 0.297816 | 0.017* | |
C4 | 0.88652 (18) | 0.60060 (4) | 0.25419 (10) | 0.01297 (17) | |
H4A | 1.015389 | 0.618103 | 0.318934 | 0.016* | |
H4B | 0.771142 | 0.591209 | 0.299868 | 0.016* | |
C5 | 0.7827 (2) | 0.63885 (4) | 0.14264 (12) | 0.0171 (2) | |
H5A | 0.733354 | 0.671460 | 0.179011 | 0.021* | |
H5B | 0.646660 | 0.622417 | 0.081279 | 0.021* | |
C6 | 0.9545 (2) | 0.65332 (5) | 0.06738 (12) | 0.0193 (2) | |
H6A | 0.880513 | 0.676399 | −0.008399 | 0.023* | |
H6B | 1.083192 | 0.673146 | 0.126156 | 0.023* | |
C7 | 1.0432 (2) | 0.60317 (5) | 0.01797 (11) | 0.0175 (2) | |
H7A | 0.917739 | 0.586222 | −0.050324 | 0.021* | |
H7B | 1.164122 | 0.612852 | −0.023344 | 0.021* | |
C8 | 1.13819 (18) | 0.56387 (5) | 0.12854 (11) | 0.01450 (18) | |
H8A | 1.181973 | 0.530931 | 0.090900 | 0.017* | |
H8B | 1.277315 | 0.578954 | 0.190121 | 0.017* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01160 (10) | 0.01244 (11) | 0.01105 (10) | 0.00005 (8) | 0.00394 (8) | 0.00045 (8) |
O1 | 0.0273 (4) | 0.0134 (4) | 0.0232 (4) | −0.0005 (3) | 0.0148 (4) | −0.0023 (3) |
O2 | 0.0115 (3) | 0.0191 (4) | 0.0204 (4) | −0.0018 (3) | 0.0057 (3) | 0.0009 (3) |
O3 | 0.0184 (4) | 0.0218 (4) | 0.0123 (3) | −0.0007 (3) | 0.0011 (3) | 0.0046 (3) |
C9 | 0.0114 (4) | 0.0119 (4) | 0.0106 (4) | −0.0004 (3) | 0.0027 (3) | −0.0006 (3) |
C10 | 0.0118 (4) | 0.0152 (4) | 0.0150 (4) | 0.0001 (3) | 0.0015 (3) | 0.0005 (4) |
C11 | 0.0135 (4) | 0.0172 (5) | 0.0169 (5) | −0.0037 (3) | 0.0035 (3) | −0.0011 (4) |
C12 | 0.0193 (5) | 0.0138 (4) | 0.0126 (4) | −0.0030 (4) | 0.0043 (4) | −0.0004 (3) |
C13 | 0.0173 (5) | 0.0159 (4) | 0.0141 (4) | 0.0008 (4) | 0.0018 (4) | 0.0030 (4) |
C14 | 0.0117 (4) | 0.0172 (5) | 0.0142 (4) | 0.0007 (3) | 0.0018 (3) | 0.0021 (4) |
C15 | 0.0309 (6) | 0.0202 (5) | 0.0199 (5) | −0.0095 (5) | 0.0041 (5) | 0.0035 (4) |
N1 | 0.0107 (3) | 0.0126 (4) | 0.0082 (3) | 0.0002 (3) | 0.0011 (3) | 0.0001 (3) |
N2 | 0.0111 (3) | 0.0139 (4) | 0.0082 (3) | −0.0013 (3) | 0.0000 (3) | −0.0011 (3) |
N3 | 0.0154 (4) | 0.0149 (4) | 0.0103 (4) | −0.0029 (3) | 0.0012 (3) | 0.0014 (3) |
C1 | 0.0123 (4) | 0.0121 (4) | 0.0088 (4) | 0.0016 (3) | 0.0024 (3) | −0.0002 (3) |
C2 | 0.0153 (4) | 0.0143 (4) | 0.0082 (4) | −0.0001 (3) | 0.0004 (3) | 0.0017 (3) |
C3 | 0.0139 (4) | 0.0152 (4) | 0.0107 (4) | 0.0007 (3) | −0.0012 (3) | 0.0026 (3) |
C4 | 0.0155 (4) | 0.0124 (4) | 0.0113 (4) | 0.0001 (3) | 0.0042 (3) | −0.0018 (3) |
C5 | 0.0190 (5) | 0.0144 (4) | 0.0174 (5) | 0.0029 (4) | 0.0045 (4) | 0.0029 (4) |
C6 | 0.0201 (5) | 0.0182 (5) | 0.0190 (5) | −0.0013 (4) | 0.0048 (4) | 0.0060 (4) |
C7 | 0.0166 (5) | 0.0243 (5) | 0.0126 (4) | −0.0022 (4) | 0.0056 (4) | 0.0029 (4) |
C8 | 0.0115 (4) | 0.0196 (5) | 0.0132 (4) | −0.0001 (3) | 0.0047 (3) | 0.0005 (4) |
S1—O1 | 1.4563 (9) | N3—H3A | 0.8800 |
S1—O2 | 1.4564 (9) | N3—H3B | 0.8800 |
S1—O3 | 1.4624 (9) | N3—C1 | 1.3334 (13) |
S1—C9 | 1.7758 (11) | C1—C2 | 1.4998 (14) |
C9—C10 | 1.3887 (14) | C2—H2A | 0.9900 |
C9—C14 | 1.3917 (14) | C2—H2B | 0.9900 |
C10—H10 | 0.9500 | C2—C3 | 1.5163 (15) |
C10—C11 | 1.3909 (16) | C3—H3C | 0.9900 |
C11—H11 | 0.9500 | C3—H3D | 0.9900 |
C11—C12 | 1.3949 (16) | C4—H4A | 0.9900 |
C12—C13 | 1.3987 (16) | C4—H4B | 0.9900 |
C12—C15 | 1.5059 (16) | C4—C5 | 1.5168 (15) |
C13—H13 | 0.9500 | C5—H5A | 0.9900 |
C13—C14 | 1.3932 (16) | C5—H5B | 0.9900 |
C14—H14 | 0.9500 | C5—C6 | 1.5308 (17) |
C15—H15A | 0.9800 | C6—H6A | 0.9900 |
C15—H15B | 0.9800 | C6—H6B | 0.9900 |
C15—H15C | 0.9800 | C6—C7 | 1.5254 (18) |
N1—N2 | 1.4708 (12) | C7—H7A | 0.9900 |
N1—C3 | 1.5160 (13) | C7—H7B | 0.9900 |
N1—C4 | 1.5160 (13) | C7—C8 | 1.5169 (16) |
N1—C8 | 1.5041 (14) | C8—H8A | 0.9900 |
N2—C1 | 1.3075 (14) | C8—H8B | 0.9900 |
O1—S1—O2 | 112.99 (5) | C1—C2—H2A | 111.7 |
O1—S1—O3 | 112.80 (5) | C1—C2—H2B | 111.7 |
O1—S1—C9 | 105.37 (5) | C1—C2—C3 | 100.52 (8) |
O2—S1—O3 | 112.52 (5) | H2A—C2—H2B | 109.4 |
O2—S1—C9 | 105.85 (5) | C3—C2—H2A | 111.7 |
O3—S1—C9 | 106.55 (5) | C3—C2—H2B | 111.7 |
C10—C9—S1 | 119.55 (8) | N1—C3—C2 | 102.27 (8) |
C10—C9—C14 | 119.99 (10) | N1—C3—H3C | 111.3 |
C14—C9—S1 | 120.38 (8) | N1—C3—H3D | 111.3 |
C9—C10—H10 | 120.2 | C2—C3—H3C | 111.3 |
C9—C10—C11 | 119.60 (10) | C2—C3—H3D | 111.3 |
C11—C10—H10 | 120.2 | H3C—C3—H3D | 109.2 |
C10—C11—H11 | 119.3 | N1—C4—H4A | 109.3 |
C10—C11—C12 | 121.38 (10) | N1—C4—H4B | 109.3 |
C12—C11—H11 | 119.3 | N1—C4—C5 | 111.53 (9) |
C11—C12—C13 | 118.30 (10) | H4A—C4—H4B | 108.0 |
C11—C12—C15 | 120.64 (11) | C5—C4—H4A | 109.3 |
C13—C12—C15 | 121.04 (11) | C5—C4—H4B | 109.3 |
C12—C13—H13 | 119.6 | C4—C5—H5A | 109.5 |
C14—C13—C12 | 120.70 (10) | C4—C5—H5B | 109.5 |
C14—C13—H13 | 119.6 | C4—C5—C6 | 110.89 (9) |
C9—C14—C13 | 120.01 (10) | H5A—C5—H5B | 108.0 |
C9—C14—H14 | 120.0 | C6—C5—H5A | 109.5 |
C13—C14—H14 | 120.0 | C6—C5—H5B | 109.5 |
C12—C15—H15A | 109.5 | C5—C6—H6A | 109.6 |
C12—C15—H15B | 109.5 | C5—C6—H6B | 109.6 |
C12—C15—H15C | 109.5 | H6A—C6—H6B | 108.2 |
H15A—C15—H15B | 109.5 | C7—C6—C5 | 110.10 (9) |
H15A—C15—H15C | 109.5 | C7—C6—H6A | 109.6 |
H15B—C15—H15C | 109.5 | C7—C6—H6B | 109.6 |
N2—N1—C3 | 106.26 (8) | C6—C7—H7A | 109.2 |
N2—N1—C4 | 109.46 (8) | C6—C7—H7B | 109.2 |
N2—N1—C8 | 110.23 (8) | H7A—C7—H7B | 107.9 |
C4—N1—C3 | 110.00 (8) | C8—C7—C6 | 111.95 (9) |
C8—N1—C3 | 110.44 (8) | C8—C7—H7A | 109.2 |
C8—N1—C4 | 110.37 (8) | C8—C7—H7B | 109.2 |
C1—N2—N1 | 106.00 (8) | N1—C8—C7 | 112.60 (9) |
H3A—N3—H3B | 120.0 | N1—C8—H8A | 109.1 |
C1—N3—H3A | 120.0 | N1—C8—H8B | 109.1 |
C1—N3—H3B | 120.0 | C7—C8—H8A | 109.1 |
N2—C1—N3 | 122.33 (9) | C7—C8—H8B | 109.1 |
N2—C1—C2 | 115.52 (9) | H8A—C8—H8B | 107.8 |
N3—C1—C2 | 122.15 (9) | ||
S1—C9—C10—C11 | 177.67 (8) | N2—N1—C3—C2 | −30.54 (10) |
S1—C9—C14—C13 | −176.66 (9) | N2—N1—C4—C5 | −65.13 (11) |
O1—S1—C9—C10 | −78.61 (10) | N2—N1—C8—C7 | 66.51 (11) |
O1—S1—C9—C14 | 98.15 (10) | N2—C1—C2—C3 | −16.10 (12) |
O2—S1—C9—C10 | 161.44 (9) | N3—C1—C2—C3 | 164.06 (10) |
O2—S1—C9—C14 | −21.79 (10) | C1—C2—C3—N1 | 26.84 (10) |
O3—S1—C9—C10 | 41.46 (10) | C3—N1—N2—C1 | 21.35 (10) |
O3—S1—C9—C14 | −141.78 (9) | C3—N1—C4—C5 | 178.47 (9) |
C9—C10—C11—C12 | −1.59 (17) | C3—N1—C8—C7 | −176.37 (9) |
C10—C9—C14—C13 | 0.09 (16) | C4—N1—N2—C1 | −97.39 (9) |
C10—C11—C12—C13 | 1.26 (17) | C4—N1—C3—C2 | 87.84 (9) |
C10—C11—C12—C15 | −177.29 (11) | C4—N1—C8—C7 | −54.52 (11) |
C11—C12—C13—C14 | −0.25 (17) | C4—C5—C6—C7 | 55.63 (13) |
C12—C13—C14—C9 | −0.41 (17) | C5—C6—C7—C8 | −53.82 (13) |
C14—C9—C10—C11 | 0.89 (16) | C6—C7—C8—N1 | 54.20 (12) |
C15—C12—C13—C14 | 178.29 (11) | C8—N1—N2—C1 | 141.04 (9) |
N1—N2—C1—N3 | 176.82 (9) | C8—N1—C3—C2 | −150.09 (9) |
N1—N2—C1—C2 | −3.02 (12) | C8—N1—C4—C5 | 56.35 (11) |
N1—C4—C5—C6 | −57.64 (12) |
C7H14N3O+·C7H7O3S− | Z = 4 |
Mr = 327.40 | F(000) = 696 |
Triclinic, P1 | Dx = 1.360 Mg m−3 |
a = 8.504 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.229 (5) Å | Cell parameters from 1568 reflections |
c = 15.834 (6) Å | θ = 2.6–25.8° |
α = 102.194 (8)° | µ = 0.22 mm−1 |
β = 91.589 (7)° | T = 120 K |
γ = 95.875 (8)° | Prism, colourless |
V = 1598.9 (11) Å3 | 0.46 × 0.21 × 0.17 mm |
Bruker APEXII CCD area detector diffractometer | 4280 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.139 |
phi and ω scans | θmax = 32.9°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −12→12 |
Tmin = 0.624, Tmax = 0.747 | k = −18→18 |
25066 measured reflections | l = −24→24 |
11813 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.085 | H-atom parameters constrained |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.010P)2 + 1.P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.005 |
11813 reflections | Δρmax = 0.53 e Å−3 |
399 parameters | Δρmin = −0.79 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. |
Refinement. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H2O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F2. Non-hydrogen atoms were refined anisotropically. All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.79797 (10) | 0.22385 (8) | 0.33622 (6) | 0.0196 (2) | |
O1 | 0.7587 (3) | 0.3252 (2) | 0.39487 (15) | 0.0266 (6) | |
O2 | 0.9663 (3) | 0.2094 (2) | 0.34222 (16) | 0.0257 (6) | |
O3 | 0.6960 (3) | 0.1233 (2) | 0.34444 (16) | 0.0292 (6) | |
C8 | 0.7628 (4) | 0.2443 (3) | 0.2302 (2) | 0.0191 (8) | |
C9 | 0.8279 (4) | 0.1778 (3) | 0.1604 (2) | 0.0254 (8) | |
H9 | 0.8894 | 0.1205 | 0.1699 | 0.030* | |
C10 | 0.8043 (4) | 0.1938 (3) | 0.0775 (2) | 0.0286 (9) | |
H10 | 0.8496 | 0.1476 | 0.0306 | 0.034* | |
C11 | 0.7126 (4) | 0.2791 (3) | 0.0617 (2) | 0.0281 (9) | |
C12 | 0.6487 (4) | 0.3443 (3) | 0.1323 (2) | 0.0274 (9) | |
H12 | 0.5873 | 0.4019 | 0.1233 | 0.033* | |
C13 | 0.6719 (4) | 0.3278 (3) | 0.2159 (2) | 0.0233 (8) | |
H13 | 0.6260 | 0.3733 | 0.2629 | 0.028* | |
C14 | 0.6896 (5) | 0.2974 (4) | −0.0289 (3) | 0.0427 (11) | |
H14A | 0.7924 | 0.3202 | −0.0502 | 0.064* | |
H14B | 0.6200 | 0.3566 | −0.0285 | 0.064* | |
H14C | 0.6414 | 0.2273 | −0.0669 | 0.064* | |
S2 | 0.78528 (10) | 0.69893 (8) | 0.34257 (6) | 0.0200 (2) | |
O5 | 0.9205 (3) | 0.7715 (2) | 0.38819 (16) | 0.0283 (6) | |
O6 | 0.6389 (3) | 0.7205 (2) | 0.38747 (16) | 0.0283 (6) | |
O7 | 0.8072 (3) | 0.58065 (19) | 0.32151 (16) | 0.0271 (6) | |
C22 | 0.7604 (4) | 0.7391 (3) | 0.2423 (2) | 0.0199 (8) | |
C23 | 0.7928 (4) | 0.6686 (3) | 0.1650 (2) | 0.0268 (9) | |
H23 | 0.8252 | 0.5967 | 0.1658 | 0.032* | |
C24 | 0.7783 (5) | 0.7018 (3) | 0.0867 (2) | 0.0311 (9) | |
H24 | 0.7983 | 0.6517 | 0.0345 | 0.037* | |
C25 | 0.7345 (4) | 0.8083 (3) | 0.0840 (2) | 0.0287 (9) | |
C26 | 0.7018 (4) | 0.8775 (3) | 0.1613 (2) | 0.0259 (8) | |
H26 | 0.6713 | 0.9499 | 0.1605 | 0.031* | |
C27 | 0.7119 (4) | 0.8452 (3) | 0.2394 (2) | 0.0225 (8) | |
H27 | 0.6863 | 0.8941 | 0.2910 | 0.027* | |
C28 | 0.7209 (5) | 0.8466 (4) | −0.0006 (3) | 0.0442 (12) | |
H28A | 0.8251 | 0.8510 | −0.0254 | 0.066* | |
H28B | 0.6825 | 0.9209 | 0.0100 | 0.066* | |
H28C | 0.6465 | 0.7926 | −0.0410 | 0.066* | |
O4 | 0.2048 (3) | −0.0119 (2) | 0.15674 (16) | 0.0336 (7) | |
N1 | 0.2362 (3) | 0.0223 (2) | 0.34354 (19) | 0.0199 (6) | |
N2 | 0.3508 (3) | −0.0574 (2) | 0.35762 (19) | 0.0217 (7) | |
N3 | 0.4101 (3) | −0.1404 (2) | 0.47208 (19) | 0.0225 (7) | |
H3A | 0.4798 | −0.1791 | 0.4424 | 0.027* | |
H3B | 0.3927 | −0.1472 | 0.5254 | 0.027* | |
C1 | 0.1901 (4) | 0.0799 (3) | 0.4326 (2) | 0.0225 (8) | |
H1A | 0.2626 | 0.1489 | 0.4564 | 0.027* | |
H1B | 0.0801 | 0.0997 | 0.4310 | 0.027* | |
C2 | 0.2059 (4) | −0.0091 (3) | 0.4848 (2) | 0.0222 (8) | |
H2A | 0.2416 | 0.0247 | 0.5456 | 0.027* | |
H2B | 0.1054 | −0.0582 | 0.4834 | 0.027* | |
C3 | 0.3310 (4) | −0.0717 (3) | 0.4364 (2) | 0.0189 (7) | |
C4 | 0.0935 (4) | −0.0433 (3) | 0.2907 (2) | 0.0234 (8) | |
H4A | 0.0487 | −0.1031 | 0.3194 | 0.028* | |
H4B | 0.0113 | 0.0075 | 0.2869 | 0.028* | |
C5 | 0.1388 (4) | −0.0955 (3) | 0.2011 (2) | 0.0288 (9) | |
H5A | 0.2172 | −0.1490 | 0.2051 | 0.035* | |
H5B | 0.0440 | −0.1383 | 0.1674 | 0.035* | |
C6 | 0.3462 (4) | 0.0471 (3) | 0.2047 (2) | 0.0321 (10) | |
H6A | 0.3936 | 0.1039 | 0.1738 | 0.038* | |
H6B | 0.4241 | −0.0070 | 0.2076 | 0.038* | |
C7 | 0.3129 (4) | 0.1049 (3) | 0.2950 (2) | 0.0254 (8) | |
H7A | 0.2422 | 0.1637 | 0.2923 | 0.031* | |
H7B | 0.4132 | 0.1420 | 0.3261 | 0.031* | |
O8 | 1.2450 (3) | 0.5115 (2) | 0.15116 (17) | 0.0364 (7) | |
N4 | 1.2217 (3) | 0.5049 (2) | 0.33160 (19) | 0.0225 (7) | |
N5 | 1.3625 (3) | 0.4490 (3) | 0.34784 (19) | 0.0224 (7) | |
N6 | 1.4441 (3) | 0.3608 (2) | 0.45482 (19) | 0.0243 (7) | |
H6C | 1.5313 | 0.3447 | 0.4285 | 0.029* | |
H6D | 1.4249 | 0.3403 | 0.5039 | 0.029* | |
C15 | 1.1372 (4) | 0.5285 (4) | 0.4154 (2) | 0.0312 (9) | |
H15A | 1.0209 | 0.5183 | 0.4043 | 0.037* | |
H15B | 1.1697 | 0.6060 | 0.4488 | 0.037* | |
C16 | 1.1897 (4) | 0.4418 (3) | 0.4631 (2) | 0.0229 (8) | |
H16A | 1.2083 | 0.4736 | 0.5259 | 0.027* | |
H16B | 1.1115 | 0.3741 | 0.4540 | 0.027* | |
C17 | 1.3410 (4) | 0.4163 (3) | 0.4203 (2) | 0.0207 (8) | |
C18 | 1.1156 (4) | 0.4280 (3) | 0.2608 (2) | 0.0253 (8) | |
H18A | 1.0869 | 0.3551 | 0.2774 | 0.030* | |
H18B | 1.0169 | 0.4622 | 0.2535 | 0.030* | |
C19 | 1.1977 (5) | 0.4083 (3) | 0.1766 (2) | 0.0330 (10) | |
H19A | 1.2920 | 0.3690 | 0.1829 | 0.040* | |
H19B | 1.1252 | 0.3592 | 0.1309 | 0.040* | |
C20 | 1.3494 (5) | 0.5831 (3) | 0.2164 (3) | 0.0351 (10) | |
H20A | 1.3825 | 0.6539 | 0.1976 | 0.042* | |
H20B | 1.4454 | 0.5458 | 0.2235 | 0.042* | |
C21 | 1.2743 (4) | 0.6103 (3) | 0.3014 (3) | 0.0295 (9) | |
H21A | 1.1821 | 0.6519 | 0.2956 | 0.035* | |
H21B | 1.3512 | 0.6593 | 0.3449 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0119 (4) | 0.0234 (5) | 0.0244 (5) | 0.0056 (4) | 0.0005 (4) | 0.0052 (4) |
O1 | 0.0302 (15) | 0.0276 (14) | 0.0214 (14) | 0.0156 (11) | 0.0010 (11) | −0.0021 (11) |
O2 | 0.0106 (12) | 0.0354 (15) | 0.0334 (15) | 0.0092 (11) | 0.0001 (10) | 0.0098 (12) |
O3 | 0.0240 (14) | 0.0279 (15) | 0.0367 (16) | −0.0071 (11) | −0.0014 (12) | 0.0145 (13) |
C8 | 0.0121 (17) | 0.0227 (19) | 0.0219 (19) | 0.0012 (14) | −0.0004 (14) | 0.0037 (15) |
C9 | 0.0194 (19) | 0.030 (2) | 0.029 (2) | 0.0094 (16) | 0.0030 (16) | 0.0076 (17) |
C10 | 0.026 (2) | 0.032 (2) | 0.026 (2) | 0.0106 (17) | 0.0040 (17) | −0.0001 (18) |
C11 | 0.024 (2) | 0.034 (2) | 0.027 (2) | 0.0040 (17) | −0.0007 (17) | 0.0087 (18) |
C12 | 0.025 (2) | 0.033 (2) | 0.027 (2) | 0.0135 (17) | 0.0002 (16) | 0.0092 (18) |
C13 | 0.0198 (19) | 0.029 (2) | 0.0220 (19) | 0.0074 (16) | −0.0006 (15) | 0.0050 (16) |
C14 | 0.048 (3) | 0.055 (3) | 0.029 (2) | 0.012 (2) | 0.001 (2) | 0.015 (2) |
S2 | 0.0133 (4) | 0.0232 (5) | 0.0247 (5) | 0.0067 (4) | 0.0015 (4) | 0.0058 (4) |
O5 | 0.0233 (14) | 0.0319 (15) | 0.0286 (14) | −0.0032 (12) | −0.0066 (11) | 0.0084 (12) |
O6 | 0.0175 (13) | 0.0377 (16) | 0.0359 (16) | 0.0155 (11) | 0.0132 (11) | 0.0142 (13) |
O7 | 0.0325 (15) | 0.0173 (13) | 0.0334 (15) | 0.0130 (11) | −0.0013 (12) | 0.0053 (12) |
C22 | 0.0145 (17) | 0.0232 (19) | 0.0212 (19) | 0.0034 (14) | −0.0012 (14) | 0.0024 (16) |
C23 | 0.026 (2) | 0.026 (2) | 0.029 (2) | 0.0100 (16) | 0.0024 (17) | 0.0045 (17) |
C24 | 0.036 (2) | 0.035 (2) | 0.022 (2) | 0.0078 (19) | 0.0037 (17) | 0.0016 (18) |
C25 | 0.025 (2) | 0.038 (2) | 0.024 (2) | −0.0023 (18) | −0.0050 (16) | 0.0111 (18) |
C26 | 0.0154 (18) | 0.031 (2) | 0.033 (2) | 0.0054 (16) | −0.0011 (16) | 0.0110 (18) |
C27 | 0.0141 (18) | 0.028 (2) | 0.026 (2) | 0.0058 (15) | 0.0012 (15) | 0.0063 (17) |
C28 | 0.048 (3) | 0.056 (3) | 0.031 (2) | 0.013 (2) | −0.004 (2) | 0.012 (2) |
O4 | 0.0319 (16) | 0.0460 (18) | 0.0241 (15) | 0.0035 (14) | −0.0012 (12) | 0.0108 (14) |
N1 | 0.0111 (14) | 0.0226 (16) | 0.0276 (17) | 0.0059 (12) | 0.0002 (12) | 0.0068 (13) |
N2 | 0.0113 (15) | 0.0246 (16) | 0.0306 (18) | 0.0096 (12) | −0.0016 (13) | 0.0059 (14) |
N3 | 0.0181 (16) | 0.0261 (17) | 0.0259 (17) | 0.0121 (13) | 0.0021 (13) | 0.0066 (14) |
C1 | 0.0141 (17) | 0.027 (2) | 0.026 (2) | 0.0089 (15) | 0.0013 (14) | 0.0020 (16) |
C2 | 0.0166 (18) | 0.027 (2) | 0.025 (2) | 0.0099 (15) | 0.0030 (15) | 0.0062 (16) |
C3 | 0.0099 (16) | 0.0229 (19) | 0.0246 (19) | 0.0035 (14) | 0.0016 (14) | 0.0058 (16) |
C4 | 0.0138 (18) | 0.028 (2) | 0.029 (2) | 0.0033 (15) | −0.0021 (15) | 0.0063 (17) |
C5 | 0.025 (2) | 0.034 (2) | 0.027 (2) | 0.0059 (17) | −0.0034 (17) | 0.0066 (18) |
C6 | 0.023 (2) | 0.045 (3) | 0.031 (2) | 0.0053 (18) | 0.0044 (17) | 0.014 (2) |
C7 | 0.0161 (18) | 0.028 (2) | 0.037 (2) | 0.0046 (15) | −0.0021 (16) | 0.0173 (18) |
O8 | 0.0409 (18) | 0.0415 (18) | 0.0281 (16) | −0.0020 (14) | −0.0009 (13) | 0.0136 (14) |
N4 | 0.0173 (16) | 0.0285 (18) | 0.0232 (17) | 0.0080 (13) | −0.0010 (13) | 0.0067 (14) |
N5 | 0.0153 (15) | 0.0309 (18) | 0.0243 (17) | 0.0097 (13) | −0.0002 (12) | 0.0103 (14) |
N6 | 0.0185 (16) | 0.0323 (18) | 0.0270 (17) | 0.0118 (13) | 0.0025 (13) | 0.0126 (14) |
C15 | 0.024 (2) | 0.048 (3) | 0.023 (2) | 0.0197 (18) | 0.0034 (16) | 0.0036 (19) |
C16 | 0.0140 (17) | 0.031 (2) | 0.023 (2) | 0.0044 (15) | 0.0018 (15) | 0.0039 (17) |
C17 | 0.0160 (18) | 0.026 (2) | 0.0203 (19) | 0.0034 (15) | −0.0008 (14) | 0.0046 (16) |
C18 | 0.0179 (19) | 0.032 (2) | 0.025 (2) | 0.0028 (16) | −0.0041 (15) | 0.0055 (17) |
C19 | 0.032 (2) | 0.034 (2) | 0.030 (2) | 0.0014 (18) | −0.0007 (18) | 0.0019 (19) |
C20 | 0.033 (2) | 0.036 (2) | 0.038 (2) | −0.0005 (19) | −0.002 (2) | 0.014 (2) |
C21 | 0.024 (2) | 0.023 (2) | 0.041 (2) | 0.0027 (16) | −0.0075 (18) | 0.0088 (18) |
S1—O1 | 1.458 (2) | O4—C6 | 1.444 (4) |
S1—O2 | 1.463 (2) | N1—N2 | 1.491 (4) |
S1—O3 | 1.462 (2) | N1—C1 | 1.519 (4) |
S1—C8 | 1.770 (4) | N1—C4 | 1.509 (4) |
C8—C9 | 1.392 (5) | N1—C7 | 1.502 (4) |
C8—C13 | 1.393 (5) | N2—C3 | 1.309 (4) |
C9—C10 | 1.379 (5) | N3—C3 | 1.332 (4) |
C10—C11 | 1.422 (5) | C1—C2 | 1.513 (5) |
C11—C12 | 1.388 (5) | C2—C3 | 1.506 (4) |
C11—C14 | 1.509 (5) | C4—C5 | 1.506 (5) |
C12—C13 | 1.392 (5) | C6—C7 | 1.503 (5) |
S2—O5 | 1.451 (2) | O8—C19 | 1.427 (4) |
S2—O6 | 1.470 (2) | O8—C20 | 1.425 (4) |
S2—O7 | 1.447 (2) | N4—N5 | 1.481 (4) |
S2—C22 | 1.772 (4) | N4—C15 | 1.515 (4) |
C22—C23 | 1.392 (5) | N4—C18 | 1.510 (4) |
C22—C27 | 1.410 (5) | N4—C21 | 1.499 (4) |
C23—C24 | 1.389 (5) | N5—C17 | 1.305 (4) |
C24—C25 | 1.399 (5) | N6—C17 | 1.334 (4) |
C25—C26 | 1.387 (5) | C15—C16 | 1.519 (5) |
C25—C28 | 1.514 (5) | C16—C17 | 1.501 (5) |
C26—C27 | 1.378 (5) | C18—C19 | 1.508 (5) |
O4—C5 | 1.436 (4) | C20—C21 | 1.494 (5) |
O1—S1—O2 | 112.68 (15) | N2—N1—C1 | 106.5 (2) |
O1—S1—O3 | 112.50 (16) | N2—N1—C4 | 109.0 (3) |
O1—S1—C8 | 106.20 (16) | N2—N1—C7 | 109.4 (2) |
O2—S1—C8 | 105.08 (15) | C4—N1—C1 | 110.8 (3) |
O3—S1—O2 | 112.55 (15) | C7—N1—C1 | 112.0 (3) |
O3—S1—C8 | 107.17 (15) | C7—N1—C4 | 109.1 (3) |
C9—C8—S1 | 120.1 (3) | C3—N2—N1 | 105.4 (3) |
C9—C8—C13 | 119.3 (3) | C2—C1—N1 | 102.5 (3) |
C13—C8—S1 | 120.6 (3) | C3—C2—C1 | 100.3 (3) |
C10—C9—C8 | 120.9 (3) | N2—C3—N3 | 123.3 (3) |
C9—C10—C11 | 120.5 (3) | N2—C3—C2 | 115.9 (3) |
C10—C11—C14 | 120.2 (3) | N3—C3—C2 | 120.7 (3) |
C12—C11—C10 | 117.6 (3) | C5—C4—N1 | 110.4 (3) |
C12—C11—C14 | 122.2 (4) | O4—C5—C4 | 111.7 (3) |
C11—C12—C13 | 121.9 (3) | O4—C6—C7 | 112.1 (3) |
C12—C13—C8 | 119.7 (3) | C6—C7—N1 | 111.0 (3) |
O5—S2—O6 | 111.25 (16) | C20—O8—C19 | 109.9 (3) |
O5—S2—C22 | 106.13 (16) | N5—N4—C15 | 107.2 (2) |
O6—S2—C22 | 105.68 (15) | N5—N4—C18 | 109.4 (3) |
O7—S2—O5 | 114.39 (15) | N5—N4—C21 | 109.0 (3) |
O7—S2—O6 | 112.66 (15) | C18—N4—C15 | 110.7 (3) |
O7—S2—C22 | 105.98 (16) | C21—N4—C15 | 112.3 (3) |
C23—C22—S2 | 121.0 (3) | C21—N4—C18 | 108.2 (3) |
C23—C22—C27 | 118.5 (3) | C17—N5—N4 | 106.1 (3) |
C27—C22—S2 | 120.5 (3) | N4—C15—C16 | 103.4 (3) |
C24—C23—C22 | 120.9 (3) | C17—C16—C15 | 100.8 (3) |
C23—C24—C25 | 120.7 (4) | N5—C17—N6 | 123.0 (3) |
C24—C25—C28 | 121.4 (4) | N5—C17—C16 | 116.3 (3) |
C26—C25—C24 | 117.8 (3) | N6—C17—C16 | 120.7 (3) |
C26—C25—C28 | 120.8 (4) | C19—C18—N4 | 110.6 (3) |
C27—C26—C25 | 122.4 (4) | O8—C19—C18 | 111.6 (3) |
C26—C27—C22 | 119.6 (3) | O8—C20—C21 | 112.3 (3) |
C5—O4—C6 | 108.8 (3) | C20—C21—N4 | 110.6 (3) |
C7H14N3O+·C7H7O3S−·H2O | F(000) = 736 |
Mr = 345.41 | Dx = 1.365 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2022 (5) Å | Cell parameters from 8385 reflections |
b = 6.3857 (4) Å | θ = 2.5–35.4° |
c = 34.166 (2) Å | µ = 0.22 mm−1 |
β = 110.022 (1)° | T = 120 K |
V = 1681.33 (18) Å3 | Prism, colourless |
Z = 4 | 0.32 × 0.29 × 0.11 mm |
Bruker APEXII CCD diffractometer | 6412 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.039 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 36.3°, θmin = 2.5° |
Tmin = 0.650, Tmax = 0.747 | h = −13→13 |
29410 measured reflections | k = −10→10 |
7804 independent reflections | l = −55→56 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.010P)2 + 2.060P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
7804 reflections | Δρmax = 0.82 e Å−3 |
209 parameters | Δρmin = −0.67 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. |
Refinement. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H2O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F2. Non-hydrogen atoms were refined anisotropically. All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.54052 (4) | 0.27590 (4) | 0.64645 (2) | 0.01151 (5) | |
O1 | 0.40347 (12) | 0.24998 (16) | 0.66414 (3) | 0.01916 (18) | |
O2 | 0.70196 (12) | 0.17217 (15) | 0.67146 (3) | 0.01790 (18) | |
O3 | 0.56795 (13) | 0.49421 (14) | 0.63760 (3) | 0.01957 (18) | |
C8 | 0.46781 (15) | 0.14546 (18) | 0.59766 (3) | 0.01261 (19) | |
C9 | 0.33699 (17) | 0.2352 (2) | 0.56398 (4) | 0.0197 (2) | |
H9 | 0.2921 | 0.3696 | 0.5666 | 0.024* | |
C10 | 0.27316 (18) | 0.1253 (2) | 0.52653 (4) | 0.0223 (3) | |
H10 | 0.1862 | 0.1873 | 0.5034 | 0.027* | |
C11 | 0.33487 (18) | −0.0746 (2) | 0.52240 (4) | 0.0196 (2) | |
C12 | 0.46558 (19) | −0.1603 (2) | 0.55637 (4) | 0.0204 (2) | |
H12 | 0.5095 | −0.2955 | 0.5540 | 0.024* | |
C13 | 0.53304 (17) | −0.05115 (19) | 0.59384 (4) | 0.0164 (2) | |
H13 | 0.6231 | −0.1110 | 0.6166 | 0.020* | |
C14 | 0.2617 (2) | −0.1959 (3) | 0.48220 (4) | 0.0286 (3) | |
H14A | 0.1351 | −0.1816 | 0.4714 | 0.043* | |
H14B | 0.2926 | −0.3440 | 0.4874 | 0.043* | |
H14C | 0.3098 | −0.1406 | 0.4617 | 0.043* | |
O4 | 1.01656 (14) | 0.10545 (19) | 0.92155 (3) | 0.0249 (2) | |
N1 | 0.86465 (12) | 0.18465 (15) | 0.83303 (3) | 0.01179 (16) | |
N2 | 0.97895 (13) | 0.34472 (16) | 0.82508 (3) | 0.01335 (17) | |
N3 | 0.94806 (14) | 0.59263 (18) | 0.77345 (3) | 0.0183 (2) | |
H3A | 1.0550 | 0.6374 | 0.7857 | 0.022* | |
H3B | 0.8819 | 0.6507 | 0.7500 | 0.022* | |
C1 | 0.72237 (16) | 0.1424 (2) | 0.79172 (4) | 0.0165 (2) | |
H1A | 0.7571 | 0.0322 | 0.7758 | 0.020* | |
H1B | 0.6130 | 0.1005 | 0.7957 | 0.020* | |
C2 | 0.70449 (15) | 0.3533 (2) | 0.77030 (4) | 0.0163 (2) | |
H2A | 0.6734 | 0.3384 | 0.7398 | 0.020* | |
H2B | 0.6177 | 0.4431 | 0.7764 | 0.020* | |
C3 | 0.88626 (14) | 0.43668 (19) | 0.79034 (4) | 0.01288 (19) | |
C4 | 0.78809 (15) | 0.2677 (2) | 0.86451 (4) | 0.0155 (2) | |
H4A | 0.7007 | 0.1677 | 0.8674 | 0.019* | |
H4B | 0.7293 | 0.4029 | 0.8547 | 0.019* | |
C5 | 0.92998 (18) | 0.2982 (2) | 0.90640 (4) | 0.0218 (2) | |
H5A | 1.0150 | 0.4019 | 0.9036 | 0.026* | |
H5B | 0.8787 | 0.3537 | 0.9266 | 0.026* | |
C6 | 1.09951 (17) | 0.0329 (2) | 0.89351 (4) | 0.0217 (3) | |
H6A | 1.1638 | −0.0976 | 0.9046 | 0.026* | |
H6B | 1.1843 | 0.1392 | 0.8916 | 0.026* | |
C7 | 0.96949 (16) | −0.0085 (2) | 0.85035 (4) | 0.0172 (2) | |
H7A | 1.0318 | −0.0531 | 0.8315 | 0.021* | |
H7B | 0.8908 | −0.1235 | 0.8518 | 0.021* | |
O5 | 0.67215 (12) | 0.77378 (16) | 0.70574 (3) | 0.01897 (18) | |
H5C | 0.6475 | 0.6819 | 0.6866 | 0.028* | |
H5D | 0.6898 | 0.8942 | 0.6973 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01181 (11) | 0.00864 (10) | 0.01302 (11) | 0.00155 (9) | 0.00290 (8) | −0.00054 (9) |
O1 | 0.0182 (4) | 0.0215 (5) | 0.0205 (4) | −0.0009 (3) | 0.0101 (3) | −0.0045 (3) |
O2 | 0.0142 (4) | 0.0159 (4) | 0.0181 (4) | 0.0046 (3) | −0.0015 (3) | −0.0014 (3) |
O3 | 0.0255 (5) | 0.0091 (4) | 0.0225 (4) | −0.0013 (3) | 0.0062 (4) | 0.0005 (3) |
C8 | 0.0140 (4) | 0.0111 (4) | 0.0121 (4) | 0.0009 (4) | 0.0037 (4) | 0.0007 (4) |
C9 | 0.0205 (5) | 0.0162 (5) | 0.0181 (5) | 0.0045 (4) | 0.0009 (4) | 0.0003 (4) |
C10 | 0.0223 (6) | 0.0236 (6) | 0.0154 (5) | 0.0011 (5) | −0.0009 (4) | 0.0013 (5) |
C11 | 0.0230 (6) | 0.0216 (6) | 0.0137 (5) | −0.0045 (5) | 0.0057 (4) | −0.0024 (4) |
C12 | 0.0285 (6) | 0.0157 (5) | 0.0168 (5) | 0.0018 (5) | 0.0076 (5) | −0.0031 (4) |
C13 | 0.0210 (5) | 0.0136 (5) | 0.0140 (5) | 0.0040 (4) | 0.0049 (4) | −0.0005 (4) |
C14 | 0.0362 (8) | 0.0303 (8) | 0.0166 (6) | −0.0072 (6) | 0.0056 (5) | −0.0072 (5) |
O4 | 0.0228 (5) | 0.0346 (6) | 0.0169 (4) | 0.0024 (4) | 0.0061 (4) | 0.0081 (4) |
N1 | 0.0104 (4) | 0.0112 (4) | 0.0138 (4) | −0.0013 (3) | 0.0041 (3) | −0.0001 (3) |
N2 | 0.0107 (4) | 0.0146 (4) | 0.0144 (4) | −0.0023 (3) | 0.0038 (3) | 0.0023 (3) |
N3 | 0.0143 (4) | 0.0197 (5) | 0.0180 (5) | −0.0023 (4) | 0.0018 (4) | 0.0067 (4) |
C1 | 0.0145 (5) | 0.0177 (5) | 0.0141 (5) | −0.0044 (4) | 0.0009 (4) | −0.0025 (4) |
C2 | 0.0119 (4) | 0.0202 (5) | 0.0139 (5) | −0.0018 (4) | 0.0008 (4) | 0.0012 (4) |
C3 | 0.0111 (4) | 0.0142 (5) | 0.0129 (4) | 0.0000 (4) | 0.0034 (4) | −0.0002 (4) |
C4 | 0.0137 (4) | 0.0181 (5) | 0.0166 (5) | 0.0006 (4) | 0.0075 (4) | −0.0008 (4) |
C5 | 0.0231 (6) | 0.0272 (7) | 0.0145 (5) | −0.0021 (5) | 0.0057 (4) | −0.0025 (5) |
C6 | 0.0153 (5) | 0.0270 (7) | 0.0219 (6) | 0.0035 (5) | 0.0052 (4) | 0.0101 (5) |
C7 | 0.0165 (5) | 0.0132 (5) | 0.0222 (6) | 0.0024 (4) | 0.0070 (4) | 0.0035 (4) |
O5 | 0.0206 (4) | 0.0172 (4) | 0.0175 (4) | −0.0011 (3) | 0.0045 (3) | 0.0017 (3) |
S1—O1 | 1.4565 (10) | N2—C3 | 1.3092 (15) |
S1—O2 | 1.4654 (9) | N3—H3A | 0.8800 |
S1—O3 | 1.4602 (10) | N3—H3B | 0.8800 |
S1—C8 | 1.7740 (12) | N3—C3 | 1.3348 (16) |
C8—C9 | 1.3995 (17) | C1—H1A | 0.9900 |
C8—C13 | 1.3884 (17) | C1—H1B | 0.9900 |
C9—H9 | 0.9500 | C1—C2 | 1.5159 (18) |
C9—C10 | 1.3949 (19) | C2—H2A | 0.9900 |
C10—H10 | 0.9500 | C2—H2B | 0.9900 |
C10—C11 | 1.398 (2) | C2—C3 | 1.5086 (16) |
C11—C12 | 1.3941 (19) | C4—H4A | 0.9900 |
C11—C14 | 1.5108 (19) | C4—H4B | 0.9900 |
C12—H12 | 0.9500 | C4—C5 | 1.5166 (18) |
C12—C13 | 1.3947 (18) | C5—H5A | 0.9900 |
C13—H13 | 0.9500 | C5—H5B | 0.9900 |
C14—H14A | 0.9800 | C6—H6A | 0.9900 |
C14—H14B | 0.9800 | C6—H6B | 0.9900 |
C14—H14C | 0.9800 | C6—C7 | 1.5183 (19) |
O4—C5 | 1.4266 (19) | C7—H7A | 0.9900 |
O4—C6 | 1.4289 (18) | C7—H7B | 0.9900 |
N1—N2 | 1.4737 (14) | O5—H5C | 0.8501 |
N1—C1 | 1.5163 (15) | O5—H5C | 0.8501 |
N1—C4 | 1.5149 (15) | O5—H5D | 0.8502 |
N1—C7 | 1.5041 (16) | ||
O1—S1—O2 | 112.24 (6) | N1—C1—H1B | 111.4 |
O1—S1—O3 | 112.95 (6) | H1A—C1—H1B | 109.2 |
O1—S1—C8 | 106.11 (6) | C2—C1—N1 | 101.98 (9) |
O2—S1—C8 | 106.35 (5) | C2—C1—H1A | 111.4 |
O3—S1—O2 | 112.32 (6) | C2—C1—H1B | 111.4 |
O3—S1—C8 | 106.25 (6) | C1—C2—H2A | 111.7 |
C9—C8—S1 | 119.79 (9) | C1—C2—H2B | 111.7 |
C13—C8—S1 | 119.78 (9) | H2A—C2—H2B | 109.5 |
C13—C8—C9 | 120.31 (11) | C3—C2—C1 | 100.21 (9) |
C8—C9—H9 | 120.3 | C3—C2—H2A | 111.7 |
C10—C9—C8 | 119.30 (12) | C3—C2—H2B | 111.7 |
C10—C9—H9 | 120.3 | N2—C3—N3 | 122.54 (11) |
C9—C10—H10 | 119.4 | N2—C3—C2 | 115.47 (11) |
C9—C10—C11 | 121.13 (12) | N3—C3—C2 | 121.98 (10) |
C11—C10—H10 | 119.4 | N1—C4—H4A | 109.6 |
C10—C11—C14 | 120.99 (13) | N1—C4—H4B | 109.6 |
C12—C11—C10 | 118.44 (12) | N1—C4—C5 | 110.13 (10) |
C12—C11—C14 | 120.57 (13) | H4A—C4—H4B | 108.1 |
C11—C12—H12 | 119.4 | C5—C4—H4A | 109.6 |
C11—C12—C13 | 121.22 (12) | C5—C4—H4B | 109.6 |
C13—C12—H12 | 119.4 | O4—C5—C4 | 110.96 (12) |
C8—C13—C12 | 119.58 (12) | O4—C5—H5A | 109.4 |
C8—C13—H13 | 120.2 | O4—C5—H5B | 109.4 |
C12—C13—H13 | 120.2 | C4—C5—H5A | 109.4 |
C11—C14—H14A | 109.5 | C4—C5—H5B | 109.4 |
C11—C14—H14B | 109.5 | H5A—C5—H5B | 108.0 |
C11—C14—H14C | 109.5 | O4—C6—H6A | 109.3 |
H14A—C14—H14B | 109.5 | O4—C6—H6B | 109.3 |
H14A—C14—H14C | 109.5 | O4—C6—C7 | 111.74 (11) |
H14B—C14—H14C | 109.5 | H6A—C6—H6B | 107.9 |
C5—O4—C6 | 109.17 (10) | C7—C6—H6A | 109.3 |
N2—N1—C1 | 106.70 (9) | C7—C6—H6B | 109.3 |
N2—N1—C4 | 109.42 (9) | N1—C7—C6 | 110.85 (11) |
N2—N1—C7 | 109.10 (9) | N1—C7—H7A | 109.5 |
C4—N1—C1 | 110.44 (9) | N1—C7—H7B | 109.5 |
C7—N1—C1 | 111.98 (10) | C6—C7—H7A | 109.5 |
C7—N1—C4 | 109.14 (9) | C6—C7—H7B | 109.5 |
C3—N2—N1 | 105.64 (9) | H7A—C7—H7B | 108.1 |
H3A—N3—H3B | 120.0 | H5C—O5—H5C | 0.0 |
C3—N3—H3A | 120.0 | H5C—O5—H5D | 112.8 |
C3—N3—H3B | 120.0 | H5C—O5—H5D | 112.8 |
N1—C1—H1A | 111.4 |
C7H14N3S+·C7H7O3S− | Z = 2 |
Mr = 343.46 | F(000) = 364 |
Triclinic, P1 | Dx = 1.357 Mg m−3 |
a = 6.2286 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.5209 (4) Å | Cell parameters from 6761 reflections |
c = 16.2157 (7) Å | θ = 2.4–30.5° |
α = 84.881 (2)° | µ = 0.33 mm−1 |
β = 79.671 (2)° | T = 295 K |
γ = 84.660 (2)° | Plate, colourless |
V = 840.68 (8) Å3 | 0.24 × 0.16 × 0.04 mm |
Bruker D8 Quest PHOTON area detector diffractometer | 4011 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.064 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 30.5°, θmin = 2.4° |
Tmin = 0.389, Tmax = 0.746 | h = −8→8 |
13223 measured reflections | k = −11→12 |
4869 independent reflections | l = −22→22 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.097 | H-atom parameters constrained |
wR(F2) = 0.218 | w = 1/[σ2(Fo2) + (0.010P)2 + 2.0384P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4869 reflections | Δρmax = 1.70 e Å−3 |
200 parameters | Δρmin = −0.57 e Å−3 |
18 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. |
Refinement. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H2O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F2. Non-hydrogen atoms were refined anisotropically. All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.06650 (13) | 0.21138 (9) | 0.84507 (5) | 0.0369 (2) | |
O1 | 0.0910 (7) | 0.3405 (5) | 0.8930 (2) | 0.0953 (13) | |
O2 | 0.1327 (7) | 0.0588 (4) | 0.8768 (3) | 0.0983 (13) | |
O3 | −0.1582 (5) | 0.2148 (5) | 0.8334 (2) | 0.0807 (10) | |
C8 | 0.2284 (5) | 0.2441 (3) | 0.74419 (18) | 0.0345 (6) | |
C9 | 0.4255 (6) | 0.3104 (5) | 0.7344 (2) | 0.0485 (8) | |
H9 | 0.4722 | 0.3450 | 0.7806 | 0.058* | |
C10 | 0.5534 (7) | 0.3252 (6) | 0.6556 (3) | 0.0627 (11) | |
H10 | 0.6869 | 0.3693 | 0.6495 | 0.075* | |
C11 | 0.4883 (7) | 0.2762 (6) | 0.5858 (2) | 0.0608 (10) | |
C12 | 0.2903 (8) | 0.2099 (6) | 0.5965 (2) | 0.0640 (11) | |
H12 | 0.2441 | 0.1755 | 0.5502 | 0.077* | |
C13 | 0.1594 (6) | 0.1938 (5) | 0.6747 (2) | 0.0524 (9) | |
H13 | 0.0260 | 0.1494 | 0.6808 | 0.063* | |
C14 | 0.6321 (11) | 0.2906 (9) | 0.4998 (3) | 0.104 (2) | |
H14A | 0.7310 | 0.3710 | 0.4985 | 0.155* | |
H14B | 0.5419 | 0.3184 | 0.4577 | 0.155* | |
H14C | 0.7142 | 0.1914 | 0.4888 | 0.155* | |
S2 | 0.8446 (2) | 0.77266 (18) | 0.64125 (7) | 0.0732 (4) | |
N1 | 0.6906 (4) | 0.7734 (3) | 0.84033 (16) | 0.0374 (5) | |
N2 | 0.5414 (4) | 0.6457 (3) | 0.85721 (16) | 0.0375 (5) | |
N3 | 0.2608 (5) | 0.5778 (4) | 0.96441 (18) | 0.0457 (7) | |
H3A | 0.2324 | 0.5006 | 0.9384 | 0.055* | |
H3B | 0.1852 | 0.5968 | 1.0128 | 0.055* | |
C1 | 0.6943 (7) | 0.8381 (5) | 0.9239 (2) | 0.0578 (10) | |
H1A | 0.7131 | 0.9505 | 0.9172 | 0.069* | |
H1B | 0.8103 | 0.7839 | 0.9508 | 0.069* | |
C2 | 0.4705 (6) | 0.8047 (4) | 0.9734 (2) | 0.0480 (8) | |
H2A | 0.4761 | 0.7760 | 1.0323 | 0.058* | |
H2B | 0.3643 | 0.8944 | 0.9686 | 0.058* | |
C3 | 0.4212 (5) | 0.6676 (3) | 0.92986 (19) | 0.0355 (6) | |
C4 | 0.9151 (6) | 0.7088 (5) | 0.8040 (2) | 0.0490 (8) | |
H4A | 0.9673 | 0.6295 | 0.8441 | 0.059* | |
H4B | 1.0128 | 0.7933 | 0.7950 | 0.059* | |
C5 | 0.9237 (7) | 0.6359 (5) | 0.7219 (3) | 0.0571 (10) | |
H5A | 0.8279 | 0.5502 | 0.7312 | 0.069* | |
H5B | 1.0716 | 0.5912 | 0.7032 | 0.069* | |
C6 | 0.5830 (7) | 0.8394 (6) | 0.6995 (3) | 0.0636 (11) | |
H6A | 0.5142 | 0.9224 | 0.6659 | 0.076* | |
H6B | 0.4893 | 0.7524 | 0.7104 | 0.076* | |
C7 | 0.6030 (6) | 0.9005 (4) | 0.7813 (2) | 0.0499 (8) | |
H7A | 0.4604 | 0.9436 | 0.8080 | 0.060* | |
H7B | 0.7000 | 0.9855 | 0.7706 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0437 (4) | 0.0326 (4) | 0.0331 (4) | −0.0058 (3) | −0.0012 (3) | −0.0037 (3) |
O1 | 0.124 (3) | 0.097 (2) | 0.0675 (19) | −0.063 (2) | 0.0222 (18) | −0.0408 (18) |
O2 | 0.103 (2) | 0.072 (2) | 0.088 (2) | 0.0258 (18) | 0.0342 (19) | 0.0316 (17) |
O3 | 0.0597 (18) | 0.110 (3) | 0.0668 (19) | −0.0114 (17) | 0.0013 (15) | 0.0018 (18) |
C8 | 0.0380 (15) | 0.0311 (13) | 0.0335 (14) | −0.0020 (11) | −0.0045 (11) | −0.0023 (10) |
C9 | 0.0439 (18) | 0.059 (2) | 0.0437 (18) | −0.0130 (15) | −0.0028 (14) | −0.0100 (15) |
C10 | 0.048 (2) | 0.078 (3) | 0.059 (2) | −0.0210 (19) | 0.0072 (17) | −0.008 (2) |
C11 | 0.064 (2) | 0.072 (3) | 0.0394 (18) | −0.004 (2) | 0.0076 (17) | −0.0014 (17) |
C12 | 0.071 (3) | 0.088 (3) | 0.0350 (18) | −0.012 (2) | −0.0081 (17) | −0.0115 (19) |
C13 | 0.054 (2) | 0.069 (2) | 0.0378 (17) | −0.0166 (18) | −0.0095 (15) | −0.0060 (16) |
C14 | 0.104 (4) | 0.141 (6) | 0.053 (3) | −0.025 (4) | 0.031 (3) | −0.011 (3) |
S2 | 0.0749 (8) | 0.1005 (10) | 0.0369 (5) | −0.0010 (6) | 0.0091 (5) | −0.0094 (5) |
N1 | 0.0454 (14) | 0.0325 (12) | 0.0337 (12) | −0.0111 (10) | −0.0002 (10) | −0.0047 (9) |
N2 | 0.0447 (14) | 0.0326 (12) | 0.0351 (12) | −0.0099 (10) | −0.0015 (10) | −0.0060 (9) |
N3 | 0.0459 (15) | 0.0479 (16) | 0.0419 (14) | −0.0149 (12) | 0.0018 (12) | −0.0038 (12) |
C1 | 0.077 (3) | 0.061 (2) | 0.0390 (17) | −0.034 (2) | 0.0022 (17) | −0.0170 (16) |
C2 | 0.066 (2) | 0.0415 (17) | 0.0354 (16) | −0.0123 (15) | 0.0022 (14) | −0.0095 (13) |
C3 | 0.0389 (15) | 0.0328 (13) | 0.0340 (14) | −0.0029 (11) | −0.0042 (11) | −0.0024 (10) |
C4 | 0.0392 (17) | 0.056 (2) | 0.0509 (19) | −0.0048 (15) | −0.0058 (14) | −0.0018 (16) |
C5 | 0.049 (2) | 0.057 (2) | 0.061 (2) | 0.0028 (17) | 0.0070 (17) | −0.0183 (18) |
C6 | 0.063 (2) | 0.080 (3) | 0.0414 (19) | 0.006 (2) | −0.0062 (17) | 0.0109 (18) |
C7 | 0.058 (2) | 0.0332 (15) | 0.0490 (19) | 0.0052 (14) | 0.0080 (16) | 0.0027 (13) |
S1—O1 | 1.437 (3) | N1—C4 | 1.492 (4) |
S1—O2 | 1.408 (3) | N1—C7 | 1.510 (4) |
S1—O3 | 1.443 (3) | N2—C3 | 1.296 (4) |
S1—C8 | 1.775 (3) | N3—H3A | 0.8600 |
C8—C9 | 1.376 (4) | N3—H3B | 0.8600 |
C8—C13 | 1.390 (4) | N3—C3 | 1.328 (4) |
C9—H9 | 0.9300 | C1—H1A | 0.9700 |
C9—C10 | 1.381 (5) | C1—H1B | 0.9700 |
C10—H10 | 0.9300 | C1—C2 | 1.517 (5) |
C10—C11 | 1.378 (6) | C2—H2A | 0.9700 |
C11—C12 | 1.380 (6) | C2—H2B | 0.9700 |
C11—C14 | 1.519 (6) | C2—C3 | 1.500 (4) |
C12—H12 | 0.9300 | C4—H4A | 0.9700 |
C12—C13 | 1.382 (5) | C4—H4B | 0.9700 |
C13—H13 | 0.9300 | C4—C5 | 1.509 (5) |
C14—H14A | 0.9600 | C5—H5A | 0.9700 |
C14—H14B | 0.9600 | C5—H5B | 0.9700 |
C14—H14C | 0.9600 | C6—H6A | 0.9700 |
S2—C5 | 1.779 (5) | C6—H6B | 0.9700 |
S2—C6 | 1.801 (4) | C6—C7 | 1.497 (6) |
N1—N2 | 1.472 (3) | C7—H7A | 0.9700 |
N1—C1 | 1.512 (4) | C7—H7B | 0.9700 |
O1—S1—O3 | 109.4 (3) | C3—N3—H3B | 120.0 |
O1—S1—C8 | 107.08 (18) | N1—C1—H1A | 111.3 |
O2—S1—O1 | 116.8 (3) | N1—C1—H1B | 111.3 |
O2—S1—O3 | 109.0 (3) | N1—C1—C2 | 102.5 (3) |
O2—S1—C8 | 106.86 (18) | H1A—C1—H1B | 109.2 |
O3—S1—C8 | 107.25 (18) | C2—C1—H1A | 111.3 |
C9—C8—S1 | 121.1 (2) | C2—C1—H1B | 111.3 |
C9—C8—C13 | 119.8 (3) | C1—C2—H2A | 111.6 |
C13—C8—S1 | 119.0 (3) | C1—C2—H2B | 111.6 |
C8—C9—H9 | 120.2 | H2A—C2—H2B | 109.4 |
C8—C9—C10 | 119.5 (3) | C3—C2—C1 | 100.6 (3) |
C10—C9—H9 | 120.2 | C3—C2—H2A | 111.6 |
C9—C10—H10 | 119.1 | C3—C2—H2B | 111.6 |
C11—C10—C9 | 121.7 (4) | N2—C3—N3 | 123.2 (3) |
C11—C10—H10 | 119.1 | N2—C3—C2 | 115.9 (3) |
C10—C11—C12 | 118.1 (4) | N3—C3—C2 | 120.9 (3) |
C10—C11—C14 | 121.2 (5) | N1—C4—H4A | 109.0 |
C12—C11—C14 | 120.6 (5) | N1—C4—H4B | 109.0 |
C11—C12—H12 | 119.4 | N1—C4—C5 | 112.9 (3) |
C11—C12—C13 | 121.2 (4) | H4A—C4—H4B | 107.8 |
C13—C12—H12 | 119.4 | C5—C4—H4A | 109.0 |
C8—C13—H13 | 120.2 | C5—C4—H4B | 109.0 |
C12—C13—C8 | 119.6 (4) | S2—C5—H5A | 108.9 |
C12—C13—H13 | 120.2 | S2—C5—H5B | 108.9 |
C11—C14—H14A | 109.5 | C4—C5—S2 | 113.4 (3) |
C11—C14—H14B | 109.5 | C4—C5—H5A | 108.9 |
C11—C14—H14C | 109.5 | C4—C5—H5B | 108.9 |
H14A—C14—H14B | 109.5 | H5A—C5—H5B | 107.7 |
H14A—C14—H14C | 109.5 | S2—C6—H6A | 109.2 |
H14B—C14—H14C | 109.5 | S2—C6—H6B | 109.2 |
C5—S2—C6 | 96.39 (18) | H6A—C6—H6B | 107.9 |
N2—N1—C1 | 106.8 (2) | C7—C6—S2 | 112.2 (3) |
N2—N1—C4 | 109.9 (2) | C7—C6—H6A | 109.2 |
N2—N1—C7 | 108.9 (3) | C7—C6—H6B | 109.2 |
C4—N1—C1 | 109.6 (3) | N1—C7—H7A | 109.2 |
C4—N1—C7 | 111.3 (3) | N1—C7—H7B | 109.2 |
C7—N1—C1 | 110.2 (3) | C6—C7—N1 | 112.2 (3) |
C3—N2—N1 | 106.2 (2) | C6—C7—H7A | 109.2 |
H3A—N3—H3B | 120.0 | C6—C7—H7B | 109.2 |
C3—N3—H3A | 120.0 | H7A—C7—H7B | 107.9 |
C13H19N4+·C7H7O3S− | Z = 4 |
Mr = 402.51 | F(000) = 856 |
Triclinic, P1 | Dx = 1.338 Mg m−3 |
a = 8.4423 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.0126 (4) Å | Cell parameters from 5975 reflections |
c = 20.3063 (6) Å | θ = 2.4–30.5° |
α = 100.315 (1)° | µ = 0.19 mm−1 |
β = 96.533 (1)° | T = 100 K |
γ = 95.678 (2)° | Plate, colourless |
V = 1997.85 (11) Å3 | 0.28 × 0.16 × 0.03 mm |
Bruker D8 Quest PHOTON detector diffractometer | 8283 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
phi and ω scans | θmax = 30.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −12→12 |
Tmin = 0.693, Tmax = 0.746 | k = −17→16 |
32048 measured reflections | l = −29→28 |
12050 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.047P)2 + 0.5831P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.005 |
12050 reflections | Δρmax = 0.44 e Å−3 |
507 parameters | Δρmin = −0.51 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. |
Refinement. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H2O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F2. Non-hydrogen atoms were refined anisotropically. All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1. |
x | y | z | Uiso*/Ueq | ||
S1A | 0.22897 (5) | 0.27108 (3) | 0.62635 (2) | 0.01242 (9) | |
O1A | 0.33527 (16) | 0.36856 (11) | 0.61689 (6) | 0.0205 (3) | |
O2A | 0.25158 (16) | 0.16556 (11) | 0.58232 (6) | 0.0187 (3) | |
O3A | 0.06131 (15) | 0.29161 (11) | 0.62272 (6) | 0.0182 (3) | |
C14A | 0.2841 (2) | 0.25202 (14) | 0.71034 (8) | 0.0143 (3) | |
C15A | 0.2317 (3) | 0.32296 (18) | 0.76325 (10) | 0.0295 (5) | |
H15A | 0.1674 | 0.3807 | 0.7545 | 0.035* | |
C16A | 0.2742 (4) | 0.3086 (2) | 0.82885 (10) | 0.0399 (6) | |
H16A | 0.2383 | 0.3570 | 0.8650 | 0.048* | |
C17A | 0.3684 (3) | 0.22468 (19) | 0.84311 (10) | 0.0303 (5) | |
C18A | 0.4160 (3) | 0.15363 (17) | 0.78939 (10) | 0.0227 (4) | |
H18A | 0.4785 | 0.0950 | 0.7981 | 0.027* | |
C19A | 0.3748 (2) | 0.16586 (15) | 0.72286 (9) | 0.0176 (4) | |
H19A | 0.4082 | 0.1160 | 0.6866 | 0.021* | |
C20A | 0.4125 (4) | 0.2097 (2) | 0.91504 (11) | 0.0496 (8) | |
H20A | 0.4412 | 0.2847 | 0.9446 | 0.074* | |
H20B | 0.5041 | 0.1658 | 0.9174 | 0.074* | |
H20C | 0.3206 | 0.1689 | 0.9297 | 0.074* | |
S1B | 0.76188 (5) | 0.20010 (4) | 0.37318 (2) | 0.01294 (9) | |
O1B | 0.90086 (17) | 0.27540 (12) | 0.41026 (6) | 0.0246 (3) | |
O2B | 0.78796 (18) | 0.08137 (11) | 0.36021 (6) | 0.0214 (3) | |
O3B | 0.61544 (16) | 0.21880 (11) | 0.40376 (7) | 0.0207 (3) | |
C14B | 0.7299 (2) | 0.23792 (15) | 0.29212 (8) | 0.0149 (3) | |
C15B | 0.7849 (2) | 0.17221 (15) | 0.23751 (9) | 0.0190 (4) | |
H15B | 0.8329 | 0.1056 | 0.2430 | 0.023* | |
C16B | 0.7689 (3) | 0.20502 (17) | 0.17479 (9) | 0.0224 (4) | |
H16B | 0.8069 | 0.1603 | 0.1377 | 0.027* | |
C17B | 0.6987 (2) | 0.30145 (17) | 0.16550 (9) | 0.0225 (4) | |
C18B | 0.6424 (3) | 0.36536 (17) | 0.22052 (10) | 0.0249 (4) | |
H18B | 0.5928 | 0.4312 | 0.2147 | 0.030* | |
C19B | 0.6574 (2) | 0.33474 (16) | 0.28367 (9) | 0.0208 (4) | |
H19B | 0.6187 | 0.3793 | 0.3206 | 0.025* | |
C20B | 0.6873 (3) | 0.3396 (2) | 0.09798 (10) | 0.0330 (5) | |
H20D | 0.7812 | 0.3942 | 0.0974 | 0.049* | |
H20E | 0.5893 | 0.3759 | 0.0912 | 0.049* | |
H20F | 0.6842 | 0.2732 | 0.0617 | 0.049* | |
N1A | 0.21592 (18) | 0.52737 (12) | 0.37860 (7) | 0.0127 (3) | |
N2A | 0.33798 (18) | 0.45039 (12) | 0.38983 (7) | 0.0145 (3) | |
N3A | 0.41482 (19) | 0.35688 (12) | 0.47664 (7) | 0.0159 (3) | |
H3AA | 0.4855 | 0.3235 | 0.4539 | 0.019* | |
H3AB | 0.4029 | 0.3437 | 0.5172 | 0.019* | |
N4A | 0.1726 (2) | 0.51015 (13) | 0.23363 (7) | 0.0182 (3) | |
C1A | 0.3258 (2) | 0.42746 (14) | 0.44972 (8) | 0.0138 (3) | |
C2A | 0.2018 (2) | 0.48318 (15) | 0.48668 (9) | 0.0154 (3) | |
H2AA | 0.2439 | 0.5147 | 0.5346 | 0.018* | |
H2AB | 0.1033 | 0.4297 | 0.4841 | 0.018* | |
C3A | 0.1721 (2) | 0.57666 (15) | 0.44743 (8) | 0.0162 (3) | |
H3AC | 0.2415 | 0.6485 | 0.4683 | 0.019* | |
H3AD | 0.0583 | 0.5910 | 0.4443 | 0.019* | |
C4A | 0.0711 (2) | 0.46040 (15) | 0.33313 (9) | 0.0159 (3) | |
H4AA | −0.0148 | 0.5101 | 0.3289 | 0.019* | |
H4AB | 0.0298 | 0.3961 | 0.3534 | 0.019* | |
C5A | 0.1141 (2) | 0.41488 (15) | 0.26387 (9) | 0.0183 (4) | |
H5AA | 0.1983 | 0.3637 | 0.2678 | 0.022* | |
H5AB | 0.0184 | 0.3704 | 0.2348 | 0.022* | |
C6A | 0.3183 (2) | 0.57318 (15) | 0.27534 (9) | 0.0173 (4) | |
H6AA | 0.3590 | 0.6365 | 0.2542 | 0.021* | |
H6AB | 0.4025 | 0.5218 | 0.2781 | 0.021* | |
C7A | 0.2836 (2) | 0.62043 (14) | 0.34553 (8) | 0.0147 (3) | |
H7AA | 0.3839 | 0.6604 | 0.3733 | 0.018* | |
H7AB | 0.2059 | 0.6766 | 0.3430 | 0.018* | |
C8A | 0.1846 (3) | 0.48537 (17) | 0.16327 (9) | 0.0240 (4) | |
C9A | 0.2072 (4) | 0.5767 (2) | 0.13014 (11) | 0.0434 (7) | |
H9A | 0.2170 | 0.6526 | 0.1549 | 0.052* | |
C10A | 0.2156 (5) | 0.5574 (3) | 0.06155 (13) | 0.0663 (11) | |
H10A | 0.2302 | 0.6202 | 0.0394 | 0.080* | |
C11A | 0.2030 (5) | 0.4474 (3) | 0.02493 (12) | 0.0644 (10) | |
H11A | 0.2097 | 0.4346 | −0.0222 | 0.077* | |
C12A | 0.1806 (4) | 0.3565 (2) | 0.05725 (12) | 0.0472 (7) | |
H12A | 0.1717 | 0.2808 | 0.0323 | 0.057* | |
C13A | 0.1710 (3) | 0.37502 (19) | 0.12624 (10) | 0.0316 (5) | |
H13A | 0.1551 | 0.3120 | 0.1481 | 0.038* | |
N1B | 0.80637 (18) | −0.00380 (12) | 0.63126 (7) | 0.0144 (3) | |
N2B | 0.65824 (18) | 0.04813 (12) | 0.61763 (7) | 0.0148 (3) | |
N3B | 0.55495 (19) | 0.13834 (12) | 0.53314 (7) | 0.0160 (3) | |
H3BA | 0.4700 | 0.1519 | 0.5533 | 0.019* | |
H3BB | 0.5657 | 0.1608 | 0.4948 | 0.019* | |
N4B | 0.81343 (19) | −0.01232 (13) | 0.77410 (7) | 0.0177 (3) | |
C1B | 0.6674 (2) | 0.08371 (14) | 0.56074 (8) | 0.0140 (3) | |
C2B | 0.8150 (2) | 0.06218 (15) | 0.52832 (9) | 0.0166 (3) | |
H2BA | 0.8920 | 0.1323 | 0.5354 | 0.020* | |
H2BB | 0.7883 | 0.0311 | 0.4793 | 0.020* | |
C3B | 0.8799 (2) | −0.02526 (17) | 0.56597 (9) | 0.0193 (4) | |
H3BC | 0.9987 | −0.0129 | 0.5748 | 0.023* | |
H3BD | 0.8450 | −0.1038 | 0.5404 | 0.023* | |
C4B | 0.9214 (2) | 0.07556 (15) | 0.68588 (9) | 0.0162 (3) | |
H4BA | 0.9455 | 0.1493 | 0.6716 | 0.019* | |
H4BB | 1.0234 | 0.0423 | 0.6926 | 0.019* | |
C5B | 0.8518 (2) | 0.09573 (15) | 0.75176 (9) | 0.0175 (4) | |
H5BA | 0.9301 | 0.1473 | 0.7867 | 0.021* | |
H5BB | 0.7531 | 0.1331 | 0.7458 | 0.021* | |
C6B | 0.7008 (2) | −0.09183 (15) | 0.72248 (9) | 0.0171 (4) | |
H6BA | 0.5973 | −0.0602 | 0.7164 | 0.021* | |
H6BB | 0.6803 | −0.1651 | 0.7377 | 0.021* | |
C7B | 0.7668 (2) | −0.11262 (15) | 0.65576 (9) | 0.0178 (4) | |
H7BA | 0.8650 | −0.1507 | 0.6610 | 0.021* | |
H7BB | 0.6867 | −0.1643 | 0.6216 | 0.021* | |
C8B | 0.7837 (2) | −0.00414 (16) | 0.84190 (9) | 0.0190 (4) | |
C9B | 0.6624 (3) | −0.07563 (17) | 0.86021 (10) | 0.0229 (4) | |
H9B | 0.5940 | −0.1295 | 0.8263 | 0.028* | |
C10B | 0.6412 (3) | −0.06842 (19) | 0.92796 (10) | 0.0296 (5) | |
H10B | 0.5592 | −0.1185 | 0.9396 | 0.036* | |
C11B | 0.7363 (3) | 0.0094 (2) | 0.97812 (10) | 0.0344 (5) | |
H11B | 0.7201 | 0.0142 | 1.0240 | 0.041* | |
C12B | 0.8566 (4) | 0.0810 (2) | 0.96025 (11) | 0.0461 (7) | |
H12B | 0.9233 | 0.1356 | 0.9944 | 0.055* | |
C13B | 0.8809 (3) | 0.0739 (2) | 0.89359 (10) | 0.0362 (6) | |
H13B | 0.9651 | 0.1230 | 0.8827 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0109 (2) | 0.01409 (19) | 0.01302 (19) | 0.00214 (15) | 0.00159 (15) | 0.00424 (15) |
O1A | 0.0181 (7) | 0.0231 (7) | 0.0205 (6) | −0.0035 (5) | 0.0010 (5) | 0.0090 (5) |
O2A | 0.0214 (7) | 0.0193 (6) | 0.0152 (6) | 0.0073 (5) | 0.0017 (5) | 0.0006 (5) |
O3A | 0.0116 (6) | 0.0232 (6) | 0.0219 (6) | 0.0059 (5) | 0.0030 (5) | 0.0074 (5) |
C14A | 0.0147 (9) | 0.0152 (8) | 0.0132 (7) | 0.0019 (6) | 0.0017 (6) | 0.0038 (6) |
C15A | 0.0462 (14) | 0.0291 (10) | 0.0180 (9) | 0.0236 (10) | 0.0061 (9) | 0.0058 (8) |
C16A | 0.0690 (19) | 0.0404 (13) | 0.0150 (9) | 0.0306 (13) | 0.0078 (11) | 0.0032 (9) |
C17A | 0.0427 (14) | 0.0339 (11) | 0.0169 (9) | 0.0115 (10) | 0.0025 (9) | 0.0093 (8) |
C18A | 0.0237 (11) | 0.0258 (10) | 0.0218 (9) | 0.0077 (8) | 0.0021 (8) | 0.0109 (8) |
C19A | 0.0166 (9) | 0.0196 (8) | 0.0186 (8) | 0.0059 (7) | 0.0037 (7) | 0.0057 (7) |
C20A | 0.076 (2) | 0.0620 (17) | 0.0180 (10) | 0.0335 (16) | 0.0039 (12) | 0.0153 (11) |
S1B | 0.0125 (2) | 0.01444 (19) | 0.01266 (19) | 0.00213 (15) | 0.00245 (15) | 0.00379 (15) |
O1B | 0.0239 (8) | 0.0305 (7) | 0.0165 (6) | −0.0107 (6) | −0.0032 (5) | 0.0078 (6) |
O2B | 0.0297 (8) | 0.0186 (6) | 0.0190 (6) | 0.0114 (6) | 0.0048 (6) | 0.0062 (5) |
O3B | 0.0187 (7) | 0.0273 (7) | 0.0213 (6) | 0.0101 (6) | 0.0101 (5) | 0.0105 (5) |
C14B | 0.0134 (9) | 0.0181 (8) | 0.0135 (8) | 0.0001 (7) | 0.0016 (6) | 0.0048 (6) |
C15B | 0.0234 (10) | 0.0165 (8) | 0.0165 (8) | 0.0017 (7) | 0.0027 (7) | 0.0019 (7) |
C16B | 0.0276 (11) | 0.0242 (9) | 0.0137 (8) | −0.0003 (8) | 0.0027 (7) | 0.0013 (7) |
C17B | 0.0209 (10) | 0.0294 (10) | 0.0171 (8) | −0.0025 (8) | −0.0005 (7) | 0.0093 (8) |
C18B | 0.0250 (11) | 0.0282 (10) | 0.0266 (10) | 0.0093 (8) | 0.0042 (8) | 0.0151 (8) |
C19B | 0.0227 (10) | 0.0235 (9) | 0.0200 (9) | 0.0082 (8) | 0.0067 (8) | 0.0088 (7) |
C20B | 0.0394 (14) | 0.0414 (13) | 0.0205 (10) | 0.0022 (10) | 0.0027 (9) | 0.0145 (9) |
N1A | 0.0117 (7) | 0.0130 (6) | 0.0138 (7) | 0.0028 (5) | 0.0013 (5) | 0.0032 (5) |
N2A | 0.0135 (7) | 0.0153 (7) | 0.0162 (7) | 0.0056 (6) | 0.0021 (6) | 0.0046 (5) |
N3A | 0.0172 (8) | 0.0169 (7) | 0.0159 (7) | 0.0066 (6) | 0.0040 (6) | 0.0057 (6) |
N4A | 0.0227 (9) | 0.0194 (7) | 0.0123 (7) | −0.0008 (6) | 0.0024 (6) | 0.0042 (6) |
C1A | 0.0135 (8) | 0.0127 (7) | 0.0149 (8) | 0.0009 (6) | 0.0016 (6) | 0.0025 (6) |
C2A | 0.0153 (9) | 0.0173 (8) | 0.0155 (8) | 0.0041 (7) | 0.0043 (7) | 0.0055 (6) |
C3A | 0.0174 (9) | 0.0180 (8) | 0.0143 (8) | 0.0062 (7) | 0.0040 (7) | 0.0027 (6) |
C4A | 0.0122 (8) | 0.0168 (8) | 0.0185 (8) | −0.0009 (7) | 0.0011 (7) | 0.0050 (7) |
C5A | 0.0210 (10) | 0.0152 (8) | 0.0176 (8) | −0.0017 (7) | 0.0013 (7) | 0.0032 (7) |
C6A | 0.0191 (9) | 0.0175 (8) | 0.0165 (8) | 0.0008 (7) | 0.0054 (7) | 0.0056 (7) |
C7A | 0.0148 (9) | 0.0132 (8) | 0.0165 (8) | 0.0010 (6) | 0.0018 (6) | 0.0048 (6) |
C8A | 0.0295 (11) | 0.0289 (10) | 0.0144 (8) | 0.0048 (9) | 0.0035 (8) | 0.0050 (7) |
C9A | 0.080 (2) | 0.0346 (12) | 0.0193 (10) | 0.0101 (13) | 0.0140 (12) | 0.0082 (9) |
C10A | 0.125 (3) | 0.0551 (17) | 0.0232 (12) | 0.0072 (19) | 0.0202 (16) | 0.0160 (12) |
C11A | 0.111 (3) | 0.0659 (19) | 0.0147 (11) | 0.004 (2) | 0.0165 (15) | 0.0024 (12) |
C12A | 0.065 (2) | 0.0464 (15) | 0.0242 (11) | −0.0029 (14) | 0.0125 (12) | −0.0082 (10) |
C13A | 0.0395 (14) | 0.0316 (11) | 0.0208 (10) | −0.0001 (10) | 0.0067 (9) | −0.0018 (8) |
N1B | 0.0125 (7) | 0.0180 (7) | 0.0137 (7) | 0.0054 (6) | 0.0030 (6) | 0.0024 (5) |
N2B | 0.0113 (7) | 0.0192 (7) | 0.0149 (7) | 0.0055 (6) | 0.0032 (6) | 0.0032 (6) |
N3B | 0.0173 (8) | 0.0166 (7) | 0.0156 (7) | 0.0048 (6) | 0.0031 (6) | 0.0049 (6) |
N4B | 0.0194 (8) | 0.0183 (7) | 0.0146 (7) | −0.0015 (6) | 0.0017 (6) | 0.0035 (6) |
C1B | 0.0148 (9) | 0.0127 (8) | 0.0131 (7) | −0.0002 (6) | 0.0018 (6) | 0.0001 (6) |
C2B | 0.0152 (9) | 0.0204 (8) | 0.0146 (8) | 0.0034 (7) | 0.0045 (7) | 0.0023 (7) |
C3B | 0.0173 (9) | 0.0283 (10) | 0.0144 (8) | 0.0101 (8) | 0.0065 (7) | 0.0024 (7) |
C4B | 0.0135 (9) | 0.0186 (8) | 0.0165 (8) | 0.0009 (7) | 0.0014 (7) | 0.0039 (7) |
C5B | 0.0187 (9) | 0.0165 (8) | 0.0167 (8) | −0.0014 (7) | 0.0023 (7) | 0.0030 (7) |
C6B | 0.0189 (9) | 0.0153 (8) | 0.0160 (8) | −0.0012 (7) | 0.0002 (7) | 0.0030 (6) |
C7B | 0.0207 (10) | 0.0152 (8) | 0.0170 (8) | 0.0041 (7) | 0.0004 (7) | 0.0022 (6) |
C8B | 0.0192 (10) | 0.0230 (9) | 0.0154 (8) | 0.0024 (7) | 0.0028 (7) | 0.0053 (7) |
C9B | 0.0262 (11) | 0.0229 (9) | 0.0203 (9) | −0.0001 (8) | 0.0049 (8) | 0.0062 (7) |
C10B | 0.0336 (13) | 0.0343 (11) | 0.0239 (10) | 0.0010 (10) | 0.0098 (9) | 0.0117 (9) |
C11B | 0.0451 (15) | 0.0433 (13) | 0.0165 (9) | 0.0028 (11) | 0.0087 (9) | 0.0086 (9) |
C12B | 0.0576 (18) | 0.0558 (16) | 0.0160 (10) | −0.0207 (14) | −0.0003 (10) | 0.0019 (10) |
C13B | 0.0388 (14) | 0.0472 (14) | 0.0170 (9) | −0.0170 (11) | 0.0007 (9) | 0.0048 (9) |
S1A—O1A | 1.4578 (13) | C5A—H5AA | 0.9900 |
S1A—O2A | 1.4572 (13) | C5A—H5AB | 0.9900 |
S1A—O3A | 1.4565 (14) | C6A—H6AA | 0.9900 |
S1A—C14A | 1.7771 (17) | C6A—H6AB | 0.9900 |
C14A—C15A | 1.390 (3) | C6A—C7A | 1.509 (2) |
C14A—C19A | 1.389 (3) | C7A—H7AA | 0.9900 |
C15A—H15A | 0.9500 | C7A—H7AB | 0.9900 |
C15A—C16A | 1.385 (3) | C8A—C9A | 1.394 (3) |
C16A—H16A | 0.9500 | C8A—C13A | 1.389 (3) |
C16A—C17A | 1.394 (3) | C9A—H9A | 0.9500 |
C17A—C18A | 1.383 (3) | C9A—C10A | 1.382 (3) |
C17A—C20A | 1.513 (3) | C10A—H10A | 0.9500 |
C18A—H18A | 0.9500 | C10A—C11A | 1.383 (4) |
C18A—C19A | 1.394 (2) | C11A—H11A | 0.9500 |
C19A—H19A | 0.9500 | C11A—C12A | 1.380 (4) |
C20A—H20A | 0.9800 | C12A—H12A | 0.9500 |
C20A—H20B | 0.9800 | C12A—C13A | 1.391 (3) |
C20A—H20C | 0.9800 | C13A—H13A | 0.9500 |
S1B—O1B | 1.4515 (13) | N1B—N2B | 1.472 (2) |
S1B—O2B | 1.4466 (13) | N1B—C3B | 1.519 (2) |
S1B—O3B | 1.4643 (14) | N1B—C4B | 1.508 (2) |
S1B—C14B | 1.7831 (17) | N1B—C7B | 1.501 (2) |
C14B—C15B | 1.394 (3) | N2B—C1B | 1.309 (2) |
C14B—C19B | 1.395 (3) | N3B—H3BA | 0.8800 |
C15B—H15B | 0.9500 | N3B—H3BB | 0.8800 |
C15B—C16B | 1.395 (3) | N3B—C1B | 1.334 (2) |
C16B—H16B | 0.9500 | N4B—C5B | 1.469 (2) |
C16B—C17B | 1.385 (3) | N4B—C6B | 1.466 (2) |
C17B—C18B | 1.396 (3) | N4B—C8B | 1.416 (2) |
C17B—C20B | 1.517 (3) | C1B—C2B | 1.498 (3) |
C18B—H18B | 0.9500 | C2B—H2BA | 0.9900 |
C18B—C19B | 1.392 (3) | C2B—H2BB | 0.9900 |
C19B—H19B | 0.9500 | C2B—C3B | 1.515 (3) |
C20B—H20D | 0.9800 | C3B—H3BC | 0.9900 |
C20B—H20E | 0.9800 | C3B—H3BD | 0.9900 |
C20B—H20F | 0.9800 | C4B—H4BA | 0.9900 |
N1A—N2A | 1.476 (2) | C4B—H4BB | 0.9900 |
N1A—C3A | 1.518 (2) | C4B—C5B | 1.512 (2) |
N1A—C4A | 1.509 (2) | C5B—H5BA | 0.9900 |
N1A—C7A | 1.502 (2) | C5B—H5BB | 0.9900 |
N2A—C1A | 1.307 (2) | C6B—H6BA | 0.9900 |
N3A—H3AA | 0.8800 | C6B—H6BB | 0.9900 |
N3A—H3AB | 0.8800 | C6B—C7B | 1.512 (2) |
N3A—C1A | 1.335 (2) | C7B—H7BA | 0.9900 |
N4A—C5A | 1.463 (2) | C7B—H7BB | 0.9900 |
N4A—C6A | 1.467 (2) | C8B—C9B | 1.396 (3) |
N4A—C8A | 1.424 (2) | C8B—C13B | 1.398 (3) |
C1A—C2A | 1.498 (2) | C9B—H9B | 0.9500 |
C2A—H2AA | 0.9900 | C9B—C10B | 1.396 (3) |
C2A—H2AB | 0.9900 | C10B—H10B | 0.9500 |
C2A—C3A | 1.513 (2) | C10B—C11B | 1.371 (3) |
C3A—H3AC | 0.9900 | C11B—H11B | 0.9500 |
C3A—H3AD | 0.9900 | C11B—C12B | 1.388 (3) |
C4A—H4AA | 0.9900 | C12B—H12B | 0.9500 |
C4A—H4AB | 0.9900 | C12B—C13B | 1.381 (3) |
C4A—C5A | 1.513 (2) | C13B—H13B | 0.9500 |
O1A—S1A—C14A | 106.64 (8) | N4A—C6A—H6AA | 109.5 |
O2A—S1A—O1A | 112.46 (8) | N4A—C6A—H6AB | 109.5 |
O2A—S1A—C14A | 106.20 (8) | N4A—C6A—C7A | 110.58 (15) |
O3A—S1A—O1A | 112.85 (8) | H6AA—C6A—H6AB | 108.1 |
O3A—S1A—O2A | 112.69 (8) | C7A—C6A—H6AA | 109.5 |
O3A—S1A—C14A | 105.32 (8) | C7A—C6A—H6AB | 109.5 |
C15A—C14A—S1A | 118.94 (15) | N1A—C7A—C6A | 111.26 (13) |
C19A—C14A—S1A | 120.59 (14) | N1A—C7A—H7AA | 109.4 |
C19A—C14A—C15A | 120.45 (17) | N1A—C7A—H7AB | 109.4 |
C14A—C15A—H15A | 120.4 | C6A—C7A—H7AA | 109.4 |
C16A—C15A—C14A | 119.2 (2) | C6A—C7A—H7AB | 109.4 |
C16A—C15A—H15A | 120.4 | H7AA—C7A—H7AB | 108.0 |
C15A—C16A—H16A | 119.2 | C9A—C8A—N4A | 118.02 (18) |
C15A—C16A—C17A | 121.6 (2) | C13A—C8A—N4A | 123.05 (18) |
C17A—C16A—H16A | 119.2 | C13A—C8A—C9A | 118.92 (19) |
C16A—C17A—C20A | 120.8 (2) | C8A—C9A—H9A | 119.8 |
C18A—C17A—C16A | 117.95 (19) | C10A—C9A—C8A | 120.4 (2) |
C18A—C17A—C20A | 121.2 (2) | C10A—C9A—H9A | 119.8 |
C17A—C18A—H18A | 119.1 | C9A—C10A—H10A | 119.8 |
C17A—C18A—C19A | 121.72 (19) | C9A—C10A—C11A | 120.5 (3) |
C19A—C18A—H18A | 119.1 | C11A—C10A—H10A | 119.8 |
C14A—C19A—C18A | 118.99 (18) | C10A—C11A—H11A | 120.2 |
C14A—C19A—H19A | 120.5 | C12A—C11A—C10A | 119.5 (2) |
C18A—C19A—H19A | 120.5 | C12A—C11A—H11A | 120.2 |
C17A—C20A—H20A | 109.5 | C11A—C12A—H12A | 119.8 |
C17A—C20A—H20B | 109.5 | C11A—C12A—C13A | 120.4 (2) |
C17A—C20A—H20C | 109.5 | C13A—C12A—H12A | 119.8 |
H20A—C20A—H20B | 109.5 | C8A—C13A—C12A | 120.2 (2) |
H20A—C20A—H20C | 109.5 | C8A—C13A—H13A | 119.9 |
H20B—C20A—H20C | 109.5 | C12A—C13A—H13A | 119.9 |
O1B—S1B—O3B | 112.20 (8) | N2B—N1B—C3B | 107.54 (13) |
O1B—S1B—C14B | 106.29 (8) | N2B—N1B—C4B | 109.94 (13) |
O2B—S1B—O1B | 113.37 (9) | N2B—N1B—C7B | 109.48 (13) |
O2B—S1B—O3B | 112.74 (8) | C4B—N1B—C3B | 110.48 (14) |
O2B—S1B—C14B | 105.47 (8) | C7B—N1B—C3B | 111.39 (14) |
O3B—S1B—C14B | 106.04 (8) | C7B—N1B—C4B | 108.02 (13) |
C15B—C14B—S1B | 119.11 (14) | C1B—N2B—N1B | 105.85 (14) |
C15B—C14B—C19B | 120.08 (16) | H3BA—N3B—H3BB | 120.0 |
C19B—C14B—S1B | 120.75 (14) | C1B—N3B—H3BA | 120.0 |
C14B—C15B—H15B | 120.2 | C1B—N3B—H3BB | 120.0 |
C14B—C15B—C16B | 119.50 (18) | C6B—N4B—C5B | 110.79 (14) |
C16B—C15B—H15B | 120.2 | C8B—N4B—C5B | 116.43 (14) |
C15B—C16B—H16B | 119.3 | C8B—N4B—C6B | 116.90 (14) |
C17B—C16B—C15B | 121.32 (19) | N2B—C1B—N3B | 122.89 (17) |
C17B—C16B—H16B | 119.3 | N2B—C1B—C2B | 116.08 (16) |
C16B—C17B—C18B | 118.38 (17) | N3B—C1B—C2B | 121.01 (15) |
C16B—C17B—C20B | 121.21 (19) | C1B—C2B—H2BA | 111.5 |
C18B—C17B—C20B | 120.4 (2) | C1B—C2B—H2BB | 111.5 |
C17B—C18B—H18B | 119.3 | C1B—C2B—C3B | 101.15 (14) |
C19B—C18B—C17B | 121.45 (19) | H2BA—C2B—H2BB | 109.4 |
C19B—C18B—H18B | 119.3 | C3B—C2B—H2BA | 111.5 |
C14B—C19B—H19B | 120.4 | C3B—C2B—H2BB | 111.5 |
C18B—C19B—C14B | 119.26 (18) | N1B—C3B—H3BC | 111.2 |
C18B—C19B—H19B | 120.4 | N1B—C3B—H3BD | 111.2 |
C17B—C20B—H20D | 109.5 | C2B—C3B—N1B | 102.81 (14) |
C17B—C20B—H20E | 109.5 | C2B—C3B—H3BC | 111.2 |
C17B—C20B—H20F | 109.5 | C2B—C3B—H3BD | 111.2 |
H20D—C20B—H20E | 109.5 | H3BC—C3B—H3BD | 109.1 |
H20D—C20B—H20F | 109.5 | N1B—C4B—H4BA | 109.4 |
H20E—C20B—H20F | 109.5 | N1B—C4B—H4BB | 109.4 |
N2A—N1A—C3A | 106.90 (12) | N1B—C4B—C5B | 111.23 (14) |
N2A—N1A—C4A | 109.30 (13) | H4BA—C4B—H4BB | 108.0 |
N2A—N1A—C7A | 109.84 (13) | C5B—C4B—H4BA | 109.4 |
C4A—N1A—C3A | 110.90 (13) | C5B—C4B—H4BB | 109.4 |
C7A—N1A—C3A | 110.76 (13) | N4B—C5B—C4B | 110.74 (15) |
C7A—N1A—C4A | 109.11 (13) | N4B—C5B—H5BA | 109.5 |
C1A—N2A—N1A | 105.54 (14) | N4B—C5B—H5BB | 109.5 |
H3AA—N3A—H3AB | 120.0 | C4B—C5B—H5BA | 109.5 |
C1A—N3A—H3AA | 120.0 | C4B—C5B—H5BB | 109.5 |
C1A—N3A—H3AB | 120.0 | H5BA—C5B—H5BB | 108.1 |
C5A—N4A—C6A | 109.75 (14) | N4B—C6B—H6BA | 109.4 |
C8A—N4A—C5A | 116.75 (15) | N4B—C6B—H6BB | 109.4 |
C8A—N4A—C6A | 114.11 (15) | N4B—C6B—C7B | 111.11 (15) |
N2A—C1A—N3A | 122.85 (17) | H6BA—C6B—H6BB | 108.0 |
N2A—C1A—C2A | 116.04 (16) | C7B—C6B—H6BA | 109.4 |
N3A—C1A—C2A | 121.09 (15) | C7B—C6B—H6BB | 109.4 |
C1A—C2A—H2AA | 111.6 | N1B—C7B—C6B | 111.94 (14) |
C1A—C2A—H2AB | 111.6 | N1B—C7B—H7BA | 109.2 |
C1A—C2A—C3A | 100.69 (14) | N1B—C7B—H7BB | 109.2 |
H2AA—C2A—H2AB | 109.4 | C6B—C7B—H7BA | 109.2 |
C3A—C2A—H2AA | 111.6 | C6B—C7B—H7BB | 109.2 |
C3A—C2A—H2AB | 111.6 | H7BA—C7B—H7BB | 107.9 |
N1A—C3A—H3AC | 111.3 | C9B—C8B—N4B | 122.07 (16) |
N1A—C3A—H3AD | 111.3 | C9B—C8B—C13B | 117.59 (17) |
C2A—C3A—N1A | 102.33 (14) | C13B—C8B—N4B | 120.29 (17) |
C2A—C3A—H3AC | 111.3 | C8B—C9B—H9B | 119.8 |
C2A—C3A—H3AD | 111.3 | C10B—C9B—C8B | 120.44 (18) |
H3AC—C3A—H3AD | 109.2 | C10B—C9B—H9B | 119.8 |
N1A—C4A—H4AA | 109.5 | C9B—C10B—H10B | 119.3 |
N1A—C4A—H4AB | 109.5 | C11B—C10B—C9B | 121.40 (19) |
N1A—C4A—C5A | 110.69 (14) | C11B—C10B—H10B | 119.3 |
H4AA—C4A—H4AB | 108.1 | C10B—C11B—H11B | 120.8 |
C5A—C4A—H4AA | 109.5 | C10B—C11B—C12B | 118.45 (19) |
C5A—C4A—H4AB | 109.5 | C12B—C11B—H11B | 120.8 |
N4A—C5A—C4A | 109.40 (14) | C11B—C12B—H12B | 119.5 |
N4A—C5A—H5AA | 109.8 | C13B—C12B—C11B | 120.9 (2) |
N4A—C5A—H5AB | 109.8 | C13B—C12B—H12B | 119.5 |
C4A—C5A—H5AA | 109.8 | C8B—C13B—H13B | 119.4 |
C4A—C5A—H5AB | 109.8 | C12B—C13B—C8B | 121.2 (2) |
H5AA—C5A—H5AB | 108.2 | C12B—C13B—H13B | 119.4 |
C17H18N4O3S | F(000) = 752 |
Mr = 358.41 | Dx = 1.333 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0524 (12) Å | Cell parameters from 3471 reflections |
b = 19.127 (2) Å | θ = 2.2–25.1° |
c = 8.8414 (10) Å | µ = 0.21 mm−1 |
β = 107.131 (4)° | T = 120 K |
V = 1786.1 (3) Å3 | Prism, colourless |
Z = 4 | 0.33 × 0.16 × 0.12 mm |
Bruker APEX II Photon CCD detector diffractometer | 3796 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
phi and ω scans | θmax = 30.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −15→15 |
Tmin = 0.699, Tmax = 0.746 | k = −20→27 |
18771 measured reflections | l = −12→12 |
5403 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.018P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
5403 reflections | Δρmax = 0.32 e Å−3 |
227 parameters | Δρmin = −0.56 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. |
Refinement. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H2O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F2. Non-hydrogen atoms were refined anisotropically. All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.87978 (3) | 0.54882 (2) | 0.66884 (4) | 0.01927 (10) | |
O1 | 0.81067 (9) | 0.52090 (5) | 0.49557 (12) | 0.0199 (2) | |
O2 | 0.79784 (10) | 0.59401 (6) | 0.72235 (13) | 0.0250 (2) | |
O3 | 0.99582 (10) | 0.57601 (6) | 0.65191 (13) | 0.0251 (2) | |
N1 | 0.67907 (11) | 0.49769 (7) | 0.48160 (15) | 0.0194 (3) | |
N2 | 0.74128 (12) | 0.40501 (8) | 0.34614 (18) | 0.0332 (4) | |
H2A | 0.8194 | 0.4203 | 0.3648 | 0.040* | |
H2B | 0.7176 | 0.3663 | 0.2916 | 0.040* | |
N3 | 0.53801 (11) | 0.30460 (6) | 0.52345 (14) | 0.0186 (3) | |
N4 | 0.64588 (13) | 0.20850 (7) | 0.62803 (16) | 0.0271 (3) | |
C1 | 0.90775 (14) | 0.47259 (8) | 0.78355 (17) | 0.0210 (3) | |
C2 | 0.83193 (14) | 0.45676 (9) | 0.87948 (18) | 0.0255 (3) | |
H2 | 0.7666 | 0.4878 | 0.8862 | 0.031* | |
C3 | 0.85304 (15) | 0.39505 (9) | 0.96501 (19) | 0.0282 (4) | |
H3 | 0.8011 | 0.3839 | 1.0302 | 0.034* | |
C4 | 0.94855 (15) | 0.34908 (9) | 0.95760 (19) | 0.0276 (4) | |
C5 | 1.02338 (16) | 0.36665 (10) | 0.8613 (2) | 0.0326 (4) | |
H5 | 1.0895 | 0.3359 | 0.8557 | 0.039* | |
C6 | 1.00407 (15) | 0.42746 (9) | 0.7738 (2) | 0.0290 (4) | |
H6 | 1.0556 | 0.4384 | 0.7079 | 0.035* | |
C7 | 0.97145 (19) | 0.28269 (10) | 1.0532 (2) | 0.0406 (5) | |
H7A | 1.0423 | 0.2895 | 1.1493 | 0.061* | |
H7B | 0.9918 | 0.2448 | 0.9901 | 0.061* | |
H7C | 0.8951 | 0.2705 | 1.0823 | 0.061* | |
C8 | 0.65908 (13) | 0.44037 (8) | 0.40026 (16) | 0.0168 (3) | |
C9 | 0.52463 (13) | 0.41426 (8) | 0.36526 (17) | 0.0182 (3) | |
H9A | 0.5071 | 0.3813 | 0.2750 | 0.022* | |
H9B | 0.4661 | 0.4544 | 0.3329 | 0.022* | |
C10 | 0.49769 (13) | 0.37750 (8) | 0.50573 (18) | 0.0187 (3) | |
H10A | 0.5415 | 0.4031 | 0.6040 | 0.022* | |
H10B | 0.4056 | 0.3796 | 0.4924 | 0.022* | |
C11 | 0.63860 (14) | 0.27683 (8) | 0.63423 (18) | 0.0234 (3) | |
H11 | 0.6986 | 0.3044 | 0.7097 | 0.028* | |
C12 | 0.47221 (14) | 0.24900 (8) | 0.43686 (18) | 0.0191 (3) | |
C13 | 0.36041 (15) | 0.24612 (9) | 0.31158 (19) | 0.0250 (3) | |
H13 | 0.3155 | 0.2871 | 0.2669 | 0.030* | |
C14 | 0.31895 (16) | 0.18005 (9) | 0.2563 (2) | 0.0296 (4) | |
H14 | 0.2435 | 0.1755 | 0.1709 | 0.035* | |
C15 | 0.38529 (17) | 0.11961 (9) | 0.3230 (2) | 0.0308 (4) | |
H15 | 0.3530 | 0.0752 | 0.2826 | 0.037* | |
C16 | 0.49607 (17) | 0.12309 (9) | 0.4458 (2) | 0.0289 (4) | |
H16 | 0.5409 | 0.0819 | 0.4896 | 0.035* | |
C17 | 0.54035 (15) | 0.18934 (8) | 0.50366 (18) | 0.0225 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01531 (16) | 0.0210 (2) | 0.02137 (18) | −0.00196 (14) | 0.00522 (13) | −0.00340 (15) |
O1 | 0.0164 (5) | 0.0220 (6) | 0.0210 (5) | −0.0041 (4) | 0.0054 (4) | −0.0025 (4) |
O2 | 0.0218 (5) | 0.0246 (6) | 0.0285 (6) | 0.0014 (4) | 0.0073 (5) | −0.0068 (5) |
O3 | 0.0181 (5) | 0.0268 (6) | 0.0309 (6) | −0.0057 (4) | 0.0080 (4) | −0.0034 (5) |
N1 | 0.0121 (5) | 0.0210 (7) | 0.0250 (6) | −0.0018 (5) | 0.0053 (5) | −0.0028 (5) |
N2 | 0.0197 (6) | 0.0347 (9) | 0.0498 (9) | −0.0103 (6) | 0.0173 (6) | −0.0244 (7) |
N3 | 0.0177 (6) | 0.0166 (7) | 0.0222 (6) | −0.0003 (5) | 0.0072 (5) | 0.0020 (5) |
N4 | 0.0295 (7) | 0.0230 (8) | 0.0285 (7) | 0.0032 (6) | 0.0079 (6) | 0.0044 (6) |
C1 | 0.0183 (7) | 0.0242 (8) | 0.0202 (7) | 0.0001 (6) | 0.0054 (6) | −0.0016 (6) |
C2 | 0.0195 (7) | 0.0331 (10) | 0.0248 (8) | 0.0016 (7) | 0.0080 (6) | −0.0011 (7) |
C3 | 0.0246 (8) | 0.0382 (10) | 0.0225 (8) | −0.0057 (7) | 0.0081 (6) | 0.0027 (7) |
C4 | 0.0269 (8) | 0.0283 (9) | 0.0243 (8) | −0.0026 (7) | 0.0024 (6) | 0.0011 (7) |
C5 | 0.0320 (9) | 0.0313 (10) | 0.0377 (10) | 0.0089 (7) | 0.0154 (8) | 0.0049 (8) |
C6 | 0.0277 (8) | 0.0314 (10) | 0.0329 (9) | 0.0057 (7) | 0.0166 (7) | 0.0048 (7) |
C7 | 0.0426 (11) | 0.0349 (11) | 0.0422 (11) | −0.0017 (9) | 0.0094 (9) | 0.0102 (9) |
C8 | 0.0170 (6) | 0.0168 (8) | 0.0173 (7) | 0.0003 (5) | 0.0063 (5) | 0.0019 (6) |
C9 | 0.0163 (7) | 0.0175 (8) | 0.0213 (7) | 0.0001 (5) | 0.0065 (6) | 0.0002 (6) |
C10 | 0.0191 (7) | 0.0162 (7) | 0.0233 (7) | 0.0004 (6) | 0.0103 (6) | −0.0005 (6) |
C11 | 0.0223 (7) | 0.0225 (9) | 0.0244 (8) | 0.0009 (6) | 0.0054 (6) | 0.0024 (6) |
C12 | 0.0209 (7) | 0.0178 (8) | 0.0219 (7) | −0.0020 (6) | 0.0114 (6) | −0.0009 (6) |
C13 | 0.0229 (7) | 0.0276 (9) | 0.0257 (8) | −0.0013 (6) | 0.0091 (6) | −0.0015 (7) |
C14 | 0.0283 (8) | 0.0337 (10) | 0.0283 (8) | −0.0075 (7) | 0.0107 (7) | −0.0079 (7) |
C15 | 0.0419 (10) | 0.0265 (10) | 0.0304 (9) | −0.0107 (7) | 0.0206 (8) | −0.0101 (7) |
C16 | 0.0423 (10) | 0.0200 (9) | 0.0309 (9) | 0.0006 (7) | 0.0212 (8) | −0.0002 (7) |
C17 | 0.0275 (8) | 0.0212 (8) | 0.0225 (7) | 0.0012 (6) | 0.0129 (6) | 0.0020 (6) |
S1—O1 | 1.5894 (11) | C5—C6 | 1.378 (2) |
S1—O2 | 1.4295 (11) | C6—H6 | 0.9500 |
S1—O3 | 1.4321 (11) | C7—H7A | 0.9800 |
S1—C1 | 1.7508 (16) | C7—H7B | 0.9800 |
O1—N1 | 1.4907 (15) | C7—H7C | 0.9800 |
N1—C8 | 1.2941 (19) | C8—C9 | 1.5108 (19) |
N2—H2A | 0.8800 | C9—H9A | 0.9900 |
N2—H2B | 0.8800 | C9—H9B | 0.9900 |
N2—C8 | 1.3296 (18) | C9—C10 | 1.5308 (19) |
N3—C10 | 1.4582 (18) | C10—H10A | 0.9900 |
N3—C11 | 1.3549 (19) | C10—H10B | 0.9900 |
N3—C12 | 1.3849 (19) | C11—H11 | 0.9500 |
N4—C11 | 1.311 (2) | C12—C13 | 1.397 (2) |
N4—C17 | 1.396 (2) | C12—C17 | 1.399 (2) |
C1—C2 | 1.390 (2) | C13—H13 | 0.9500 |
C1—C6 | 1.393 (2) | C13—C14 | 1.383 (2) |
C2—H2 | 0.9500 | C14—H14 | 0.9500 |
C2—C3 | 1.384 (2) | C14—C15 | 1.402 (2) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C3—C4 | 1.390 (2) | C15—C16 | 1.378 (2) |
C4—C5 | 1.392 (2) | C16—H16 | 0.9500 |
C4—C7 | 1.505 (2) | C16—C17 | 1.400 (2) |
C5—H5 | 0.9500 | ||
O1—S1—C1 | 103.37 (7) | H7B—C7—H7C | 109.5 |
O2—S1—O1 | 110.53 (6) | N1—C8—N2 | 127.46 (13) |
O2—S1—O3 | 119.29 (7) | N1—C8—C9 | 112.99 (12) |
O2—S1—C1 | 109.44 (7) | N2—C8—C9 | 119.55 (13) |
O3—S1—O1 | 102.25 (6) | C8—C9—H9A | 108.8 |
O3—S1—C1 | 110.62 (7) | C8—C9—H9B | 108.8 |
N1—O1—S1 | 111.10 (8) | C8—C9—C10 | 113.60 (12) |
C8—N1—O1 | 107.52 (11) | H9A—C9—H9B | 107.7 |
H2A—N2—H2B | 120.0 | C10—C9—H9A | 108.8 |
C8—N2—H2A | 120.0 | C10—C9—H9B | 108.8 |
C8—N2—H2B | 120.0 | N3—C10—C9 | 113.58 (12) |
C11—N3—C10 | 127.75 (13) | N3—C10—H10A | 108.8 |
C11—N3—C12 | 106.50 (13) | N3—C10—H10B | 108.8 |
C12—N3—C10 | 125.51 (12) | C9—C10—H10A | 108.8 |
C11—N4—C17 | 104.31 (13) | C9—C10—H10B | 108.8 |
C2—C1—S1 | 119.97 (12) | H10A—C10—H10B | 107.7 |
C2—C1—C6 | 120.79 (15) | N3—C11—H11 | 123.0 |
C6—C1—S1 | 119.21 (12) | N4—C11—N3 | 114.07 (14) |
C1—C2—H2 | 120.5 | N4—C11—H11 | 123.0 |
C3—C2—C1 | 118.97 (15) | N3—C12—C13 | 131.80 (15) |
C3—C2—H2 | 120.5 | N3—C12—C17 | 105.26 (13) |
C2—C3—H3 | 119.3 | C13—C12—C17 | 122.91 (15) |
C2—C3—C4 | 121.45 (15) | C12—C13—H13 | 122.0 |
C4—C3—H3 | 119.3 | C14—C13—C12 | 116.08 (16) |
C3—C4—C5 | 118.19 (16) | C14—C13—H13 | 122.0 |
C3—C4—C7 | 120.78 (15) | C13—C14—H14 | 119.1 |
C5—C4—C7 | 121.03 (16) | C13—C14—C15 | 121.79 (16) |
C4—C5—H5 | 119.1 | C15—C14—H14 | 119.1 |
C6—C5—C4 | 121.70 (16) | C14—C15—H15 | 119.2 |
C6—C5—H5 | 119.1 | C16—C15—C14 | 121.65 (16) |
C1—C6—H6 | 120.6 | C16—C15—H15 | 119.2 |
C5—C6—C1 | 118.89 (15) | C15—C16—H16 | 121.1 |
C5—C6—H6 | 120.6 | C15—C16—C17 | 117.74 (16) |
C4—C7—H7A | 109.5 | C17—C16—H16 | 121.1 |
C4—C7—H7B | 109.5 | N4—C17—C12 | 109.85 (14) |
C4—C7—H7C | 109.5 | N4—C17—C16 | 130.29 (15) |
H7A—C7—H7B | 109.5 | C12—C17—C16 | 119.83 (15) |
H7A—C7—H7C | 109.5 |
Compound | Yield (%) | Time (h) | M.p. (°C) | Rf** | ||
r. t.* | 70 0C | r. t.* | 70 0C | |||
6 | 62 | 55 | 15 | 5 | 230 | 0.24 |
7 | 65 | 65 | 15 | 8 | 218–220 | 0.11 |
8a | 56 | – | 20 | – | 255 | 0.08 |
8b | 0 | 84 | – | 8 | 302 | – |
9 | 50 | 68 | 15 | 5 | 290 | 0.10 |
10 | 45 | 66 | 15 | 6 | 163–165 | 0.67 |
Notes: (*) all the experiments at room temperature (r.t.) are taken from the literature (Kayukova et al., 2021a). (**) The eluent for the TLC analysis is a EtOH–benzene mixture (1:1 v/v) plus a few drops of a 25% aqueous solution of NH3. |
N1—N2 | N2═C | N1—CPz | N1—CAr | X—CAr | CAr—N1—CAr | CPz—N1—N2 | CAr—X—CAr | d(C···Pz)a | |
6 | 1.471 (1) | 1.308 (1) | 1.516 (1) | 1.504 (1)–1.516 (1) | 1.525 (2)–1.531 (2) | 110.4 (1) | 106.3 (1) | 110.1 (1) | 0.475 (2) |
7 | 1.480 (4)–1.491 (4) | 1.304 (5)–1.309 (5) | 1.515 (4)–1.515 (4) | 1.499 (4)–1.510 (4) | 1.425 (4)–1.444 (4) | 106.5 (3)–108.2 (3) | 106.5 (3)–107.3 (3) | 108.8 (3)–109.9 (3) | 0.388 (5)–0.475 (5) |
7·H2O | 1.474 (1) | 1.309 (2) | 1.516 (2) | 1.504 (2)–1.515 (2) | 1.427 (2)–1.429 (2) | 109.1 (1) | 106.7 (1) | 109.2 (1) | 0.490 (2) |
8a | 1.472 (3) | 1.296 (4) | 1.512 (4) | 1.492 (4)–1.510 (4) | 1.779 (5)–1.801 (4) | 111.3 (2) | 106.8 (2) | 96.4 (2) | 0.441 (6) |
9 | 1.472 (2)–1.476 (2) | 1.307 (2)–1.309 (2) | 1.518 (2)–1.519 (2) | 1.501 (2)–1.509 (2) | 1.463 (3)–1.469 (2) | 108.0 (1)–109.1 (1) | 106.9 (1)–107.1 (1) | 109.8 (1)–110.8 (1) | 0.401 (3)–0.455 (2) |
Note: (a) the deviation of the C1 atom from the mean plane formed by the N—N═C—C atoms of the five-membered pyrazole ring. |
Donor | Acceptor | Observed at | ||
Propensitya | Pure solids | Hydrate | ||
N—H | O(S) | 0.99/0.99 | 6–9 | 7·H2O |
H2O | 0/0.71 | 7·H2O | ||
N2 | 0.76/0.64 | 6 | ||
O—H | O(S) | 0/0.98 | 7·H2O | |
H2O | 0/0.59 | |||
N2 | 0/0.51 |
Note: (a) values in the absence and presence of water are divided by a slash. |
Compound | D—H···A | D—H | H···A | D···A | D—H···A |
6 | N3—H3A···N2i | 0.88 | 2.173 | 3.038 (1) | 167.2 |
N3—H3B···O3ii | 0.88 | 2.132 | 2.953 (1) | 155.0 | |
7 | N3—H3A···O6iii | 0.88 | 2.012 | 2.887 (4) | 172.2 |
N3—H3B···O3iv | 0.88 | 2.186 | 3.037 (4) | 162.4 | |
N6—H6C···O1v | 0.88 | 2.044 | 2.907 (4) | 166.6 | |
N6—H6D···O6vi | 0.88 | 2.077 | 2.954 (4) | 174.0 | |
7·H2O | N3—H3A···O2vii | 0.88 | 2.041 | 2.888 (1) | 161.0 |
N3—H3B···O5 | 0.88 | 2.021 | 2.868 (1) | 161.1 | |
O5—H5C···O3 | 0.85 | 1.979 | 2.824 (1) | 172.6 | |
O5—H5D···O2viii | 0.85 | 2.000 | 2.846 (1) | 172.6 | |
8a | N3—H3A···O1 | 0.88 | 1.953 | 2.793 (6) | 165.3 |
N3—H3B···O1ix | 0.88 | 2.147 | 2.970 (6) | 159.9 | |
9 | N3A—H3AA···O3B | 0.88 | 1.972 | 2.839 (2) | 167.9 |
N3A—H3AB···O1A | 0.88 | 2.143 | 2.982 (2) | 158.9 | |
N3B—H3BA···O2A | 0.88 | 2.012 | 2.880 (2) | 168.8 | |
N3B—H3BB···O3B | 0.88 | 2.159 | 3.036 (2) | 174.8 | |
10 | N2—H2A···O3x | 0.88 | 2.092 | 2.923 (2) | 157.3 |
N2—H2B···N4xi | 0.88 | 2.023 | 2.889 (2) | 167.8 |
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z; (iv) -x+1, -y, -z+1; (v) x+1, y, z; (vi) -x+2, -y+2, -z+1; (vii) -x+2, y+1/2, -z+3/2; (viii) x, y+1, z; (ix) -x, -y+1, -z+2; (x) -x+2, -y+1, -z+1; (xi) x, -y+1/2, z-1/2. |
Compound | 6 | 7 | 8a | 9 | 10 | Acarbose |
α-Amylase activity (%) | 26.7±2.2 | 32.7±1.8 | 35.2±3.1 | 33.8±2.8 | 30.1±1.4 | 50.3±1.1 |
α-Glucosidase activity (%) | 61.0±14.4 | No activity | 36.6±22.7 | 45.5±6.4 | 63.4±12.8 | 58.9±4.8 |
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