The structures of four salt forms of sulfadiazine (SDH) with alkali metal cations are presented. Three contain the deprotonated SD anion (C10H9N4O2S). These are the discrete complex diaqua{4-[(pyrimidin-2-ylazanidyl-κN1)sulfonyl-κO]aniline}lithium(I), [Li(SD)(H2O)2], (I), and the coordination polymers poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)], [Na(SD)]n, (II), and poly[diaqua{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}potassium(I)], [K(SD)(H2O)2]n, (III). Na complex (II) is a three-dimensional coordination polymer, whilst K complex (III) has two crystallographically independent [K(SD)(H2O)2] units per asymmetric unit (Z′ = 2) and gives a two-dimensional coordination polymer whose layers propagate parallel to the crystallographic ab plane. The different bonding modes of the SD anion in these three complexes is discussed. Structure (IV) contains protonated SDH2 cations {4-[(pyrimidin-2-yl)sulfamoyl]anilinium, C10H11N4O2S} and the Orange G dianion [OG, 7-oxo-8-(phenylhydrazinylidene)naphthalene-1,3-disulfonate, C16H10N2O7S2], namely, 4-[(pyrimidin-2-yl)sulfamoyl]anilinium tetraaqua[7-oxo-8-(phenylhydrazinylidene)naphthalene-1,3-disulfonato]sodium(I) sesquihydrate, (SDH2)[Na(OG)(H2O)4]·1.5H2O. The [Na(OG)(H2O)4]2 dimers have antiparallel naphthyl ring structures joined through two Na centres that bond to the hydrazone anions through the O atoms of the ketone and sulfonate substituents. The structures of the salts formed on reaction of SDH with 2-aminopyridine and ethanolamine are also presented as 2-aminopyridinium 4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline, [C5H7N2][SD], (V), and ethanolaminium 4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline monohydrate, [HOCH2CH2NH3][SD]·H2O, (VI), respectively. Structure (V) features a heterodimeric R22(8) hydrogen-bond motif between the cation and the anion, whilst structure (VI) has a tetrameric core of two cations linked by a central R22(10) hydrogen-bonded motif which supports two anions linked to this core by R33(8) motifs.
Supporting information
CCDC references: 1828889; 1828888; 1828887; 1828886; 1828885; 1828884
For all structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014). Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for (I), (III); SHELXT (Sheldrick, 2015a) for (II), (V), (VI). For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) for (I), (II), (III), (V), (VI); SHELXT (Sheldrick, 2015a) for (IV).
Diaqua{4-[(pyrimidin-2-ylazanidyl-
κN1)sulfonyl-
κO]aniline}lithium(I) (I)
top
Crystal data top
[Li(C10H9N4O2S)(H2O)2] | F(000) = 608 |
Mr = 292.24 | Dx = 1.467 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.5095 (4) Å | Cell parameters from 2629 reflections |
b = 12.0788 (5) Å | θ = 3.2–29.8° |
c = 9.5184 (4) Å | µ = 0.26 mm−1 |
β = 91.063 (3)° | T = 123 K |
V = 1323.03 (9) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.20 × 0.18 mm |
Data collection top
Oxford Diffraction Xcalibur E diffractometer | 2184 reflections with I > 2σ(I) |
Radiation source: tube | Rint = 0.016 |
ω scans | θmax = 29.0°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | h = −15→13 |
Tmin = 0.949, Tmax = 1.000 | k = −15→15 |
3390 measured reflections | l = −12→10 |
2246 independent reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0365P)2 + 0.3087P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.026 | (Δ/σ)max < 0.001 |
wR(F2) = 0.066 | Δρmax = 0.28 e Å−3 |
S = 1.04 | Δρmin = −0.25 e Å−3 |
2246 reflections | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
207 parameters | Extinction coefficient: 0.0054 (9) |
8 restraints | Absolute structure: Refined as an inversion twin. |
Hydrogen site location: mixed | Absolute structure parameter: −0.01 (8) |
Special details top
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. Refined as a 2-component inversion twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Li1 | 0.8416 (4) | 0.2755 (4) | 0.4134 (5) | 0.0198 (8) | |
S1 | 0.75432 (4) | 0.33089 (4) | 0.70030 (5) | 0.01208 (13) | |
O1 | 0.81653 (14) | 0.36761 (14) | 0.57624 (17) | 0.0157 (3) | |
O2 | 0.72513 (14) | 0.42112 (14) | 0.79429 (18) | 0.0175 (4) | |
O1W | 0.83115 (15) | 0.36603 (15) | 0.24923 (19) | 0.0211 (4) | |
O2W | 0.97330 (16) | 0.19039 (18) | 0.3764 (2) | 0.0314 (5) | |
N1 | 0.63739 (15) | 0.26680 (16) | 0.6691 (2) | 0.0129 (4) | |
N2 | 0.71240 (17) | 0.16691 (16) | 0.4758 (2) | 0.0154 (4) | |
N3 | 0.52506 (17) | 0.13140 (17) | 0.5695 (2) | 0.0145 (4) | |
N4 | 1.05266 (19) | 0.00920 (18) | 1.0096 (2) | 0.0187 (4) | |
C1 | 0.62734 (19) | 0.18727 (19) | 0.5688 (2) | 0.0121 (4) | |
C2 | 0.6930 (2) | 0.0854 (2) | 0.3827 (3) | 0.0206 (5) | |
H2 | 0.7523 | 0.0684 | 0.3180 | 0.025* | |
C3 | 0.5921 (2) | 0.0254 (2) | 0.3763 (3) | 0.0231 (5) | |
H3 | 0.5798 | −0.0317 | 0.3091 | 0.028* | |
C4 | 0.5093 (2) | 0.0531 (2) | 0.4735 (3) | 0.0184 (5) | |
H4 | 0.4376 | 0.0141 | 0.4714 | 0.022* | |
C5 | 0.84694 (19) | 0.23972 (19) | 0.7933 (2) | 0.0137 (4) | |
C6 | 0.8089 (2) | 0.1949 (2) | 0.9188 (3) | 0.0189 (5) | |
H6 | 0.7352 | 0.2151 | 0.9541 | 0.023* | |
C7 | 0.8785 (2) | 0.1211 (2) | 0.9918 (2) | 0.0198 (5) | |
H7 | 0.8523 | 0.0904 | 1.0775 | 0.024* | |
C8 | 0.9871 (2) | 0.09088 (19) | 0.9410 (2) | 0.0161 (5) | |
C9 | 1.0257 (2) | 0.1391 (2) | 0.8169 (2) | 0.0157 (5) | |
H9 | 1.1005 | 0.1211 | 0.7830 | 0.019* | |
C10 | 0.95556 (18) | 0.21289 (19) | 0.7430 (2) | 0.0154 (5) | |
H10 | 0.9819 | 0.2450 | 0.6582 | 0.018* | |
H1W | 0.815 (3) | 0.4368 (12) | 0.251 (4) | 0.050 (11)* | |
H2W | 0.890 (2) | 0.365 (3) | 0.194 (3) | 0.055 (12)* | |
H3W | 1.017 (3) | 0.202 (3) | 0.305 (3) | 0.063 (12)* | |
H4W | 1.002 (3) | 0.131 (2) | 0.413 (4) | 0.061 (12)* | |
H1N | 1.122 (3) | 0.003 (3) | 0.985 (3) | 0.025 (8)* | |
H2N | 1.044 (2) | 0.012 (2) | 1.107 (3) | 0.017 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Li1 | 0.019 (2) | 0.019 (2) | 0.022 (2) | 0.0013 (16) | 0.0043 (15) | 0.0013 (17) |
S1 | 0.0108 (2) | 0.0113 (2) | 0.0143 (2) | −0.0013 (2) | 0.00227 (16) | −0.0006 (2) |
O1 | 0.0157 (8) | 0.0145 (8) | 0.0171 (8) | −0.0029 (6) | 0.0045 (6) | 0.0013 (7) |
O2 | 0.0178 (8) | 0.0133 (8) | 0.0213 (9) | 0.0001 (6) | 0.0032 (6) | −0.0042 (7) |
O1W | 0.0208 (9) | 0.0181 (9) | 0.0246 (9) | 0.0048 (7) | 0.0098 (7) | 0.0059 (8) |
O2W | 0.0274 (11) | 0.0332 (11) | 0.0345 (12) | 0.0151 (8) | 0.0209 (9) | 0.0194 (9) |
N1 | 0.0100 (9) | 0.0144 (9) | 0.0145 (9) | −0.0011 (7) | 0.0020 (6) | −0.0011 (8) |
N2 | 0.0140 (10) | 0.0165 (10) | 0.0160 (10) | 0.0001 (8) | 0.0049 (7) | −0.0007 (8) |
N3 | 0.0135 (9) | 0.0149 (10) | 0.0149 (9) | −0.0035 (8) | 0.0013 (7) | 0.0015 (8) |
N4 | 0.0194 (11) | 0.0187 (11) | 0.0180 (11) | 0.0018 (8) | −0.0032 (8) | −0.0010 (8) |
C1 | 0.0126 (10) | 0.0117 (10) | 0.0120 (11) | 0.0003 (8) | 0.0004 (7) | 0.0030 (8) |
C2 | 0.0230 (12) | 0.0219 (12) | 0.0172 (12) | 0.0010 (10) | 0.0071 (9) | −0.0048 (10) |
C3 | 0.0262 (13) | 0.0218 (12) | 0.0214 (13) | −0.0044 (10) | 0.0025 (9) | −0.0108 (11) |
C4 | 0.0171 (11) | 0.0182 (12) | 0.0198 (12) | −0.0042 (9) | −0.0005 (8) | 0.0008 (10) |
C5 | 0.0127 (10) | 0.0133 (11) | 0.0150 (11) | −0.0018 (8) | 0.0001 (8) | −0.0019 (9) |
C6 | 0.0157 (11) | 0.0212 (12) | 0.0200 (13) | −0.0016 (10) | 0.0029 (9) | 0.0004 (10) |
C7 | 0.0215 (12) | 0.0208 (12) | 0.0174 (12) | −0.0014 (10) | 0.0049 (9) | 0.0030 (10) |
C8 | 0.0184 (11) | 0.0142 (11) | 0.0157 (12) | −0.0026 (9) | −0.0030 (8) | −0.0031 (9) |
C9 | 0.0129 (11) | 0.0176 (12) | 0.0167 (11) | 0.0018 (9) | 0.0004 (8) | −0.0036 (9) |
C10 | 0.0139 (11) | 0.0177 (12) | 0.0145 (11) | −0.0003 (9) | 0.0027 (8) | 0.0000 (9) |
Geometric parameters (Å, º) top
Li1—O2W | 1.870 (4) | N4—C8 | 1.396 (3) |
Li1—O1W | 1.910 (5) | N4—H1N | 0.84 (3) |
Li1—O1 | 1.934 (5) | N4—H2N | 0.93 (3) |
Li1—N2 | 2.077 (5) | C2—C3 | 1.370 (4) |
Li1—S1 | 3.002 (4) | C2—H2 | 0.9500 |
S1—O2 | 1.4533 (17) | C3—C4 | 1.382 (3) |
S1—O1 | 1.4612 (16) | C3—H3 | 0.9500 |
S1—N1 | 1.5761 (19) | C4—H4 | 0.9500 |
S1—C5 | 1.760 (2) | C5—C10 | 1.385 (3) |
O1W—H1W | 0.875 (12) | C5—C6 | 1.390 (3) |
O1W—H2W | 0.867 (12) | C6—C7 | 1.378 (3) |
O2W—H3W | 0.865 (12) | C6—H6 | 0.9500 |
O2W—H4W | 0.863 (12) | C7—C8 | 1.398 (3) |
N1—C1 | 1.357 (3) | C7—H7 | 0.9500 |
N2—C2 | 1.340 (3) | C8—C9 | 1.397 (3) |
N2—C1 | 1.355 (3) | C9—C10 | 1.386 (3) |
N3—C4 | 1.325 (3) | C9—H9 | 0.9500 |
N3—C1 | 1.357 (3) | C10—H10 | 0.9500 |
| | | |
O2W—Li1—O1W | 101.5 (2) | C8—N4—H2N | 111.7 (17) |
O2W—Li1—O1 | 126.9 (2) | H1N—N4—H2N | 113 (3) |
O1W—Li1—O1 | 108.5 (2) | N2—C1—N3 | 123.4 (2) |
O2W—Li1—N2 | 107.1 (2) | N2—C1—N1 | 122.3 (2) |
O1W—Li1—N2 | 124.1 (2) | N3—C1—N1 | 114.3 (2) |
O1—Li1—N2 | 90.91 (18) | N2—C2—C3 | 123.3 (2) |
O2W—Li1—S1 | 125.5 (2) | N2—C2—H2 | 118.4 |
O1W—Li1—S1 | 126.84 (19) | C3—C2—H2 | 118.4 |
O1—Li1—S1 | 23.87 (8) | C2—C3—C4 | 115.9 (2) |
N2—Li1—S1 | 68.13 (13) | C2—C3—H3 | 122.0 |
O2—S1—O1 | 113.09 (10) | C4—C3—H3 | 122.0 |
O2—S1—N1 | 106.15 (10) | N3—C4—C3 | 123.2 (2) |
O1—S1—N1 | 115.22 (10) | N3—C4—H4 | 118.4 |
O2—S1—C5 | 107.73 (10) | C3—C4—H4 | 118.4 |
O1—S1—C5 | 107.16 (10) | C10—C5—C6 | 120.4 (2) |
N1—S1—C5 | 107.14 (10) | C10—C5—S1 | 120.99 (18) |
O2—S1—Li1 | 144.30 (11) | C6—C5—S1 | 118.58 (18) |
O1—S1—Li1 | 32.38 (11) | C7—C6—C5 | 119.7 (2) |
N1—S1—Li1 | 91.02 (11) | C7—C6—H6 | 120.1 |
C5—S1—Li1 | 96.20 (11) | C5—C6—H6 | 120.1 |
S1—O1—Li1 | 123.74 (16) | C6—C7—C8 | 120.7 (2) |
Li1—O1W—H1W | 124 (2) | C6—C7—H7 | 119.7 |
Li1—O1W—H2W | 117 (2) | C8—C7—H7 | 119.7 |
H1W—O1W—H2W | 101 (2) | N4—C8—C9 | 120.8 (2) |
Li1—O2W—H3W | 123 (3) | N4—C8—C7 | 120.1 (2) |
Li1—O2W—H4W | 134 (3) | C9—C8—C7 | 119.0 (2) |
H3W—O2W—H4W | 104 (2) | C10—C9—C8 | 120.4 (2) |
C1—N1—S1 | 122.79 (16) | C10—C9—H9 | 119.8 |
C2—N2—C1 | 116.9 (2) | C8—C9—H9 | 119.8 |
C2—N2—Li1 | 112.7 (2) | C5—C10—C9 | 119.7 (2) |
C1—N2—Li1 | 127.0 (2) | C5—C10—H10 | 120.1 |
C4—N3—C1 | 117.3 (2) | C9—C10—H10 | 120.1 |
C8—N4—H1N | 116 (2) | | |
| | | |
O2—S1—O1—Li1 | −167.45 (18) | C2—C3—C4—N3 | −1.0 (4) |
N1—S1—O1—Li1 | −45.1 (2) | O2—S1—C5—C10 | −123.58 (19) |
C5—S1—O1—Li1 | 74.0 (2) | O1—S1—C5—C10 | −1.6 (2) |
O2—S1—N1—C1 | 169.98 (18) | N1—S1—C5—C10 | 122.58 (19) |
O1—S1—N1—C1 | 44.0 (2) | Li1—S1—C5—C10 | 29.6 (2) |
C5—S1—N1—C1 | −75.1 (2) | O2—S1—C5—C6 | 56.4 (2) |
Li1—S1—N1—C1 | 21.7 (2) | O1—S1—C5—C6 | 178.37 (18) |
C2—N2—C1—N3 | −1.4 (3) | N1—S1—C5—C6 | −57.4 (2) |
Li1—N2—C1—N3 | 156.1 (2) | Li1—S1—C5—C6 | −150.4 (2) |
C2—N2—C1—N1 | 179.3 (2) | C10—C5—C6—C7 | −1.7 (4) |
Li1—N2—C1—N1 | −23.3 (4) | S1—C5—C6—C7 | 178.34 (19) |
C4—N3—C1—N2 | 0.1 (3) | C5—C6—C7—C8 | 0.1 (4) |
C4—N3—C1—N1 | 179.5 (2) | C6—C7—C8—N4 | −174.7 (2) |
S1—N1—C1—N2 | −8.8 (3) | C6—C7—C8—C9 | 1.8 (4) |
S1—N1—C1—N3 | 171.78 (16) | N4—C8—C9—C10 | 174.3 (2) |
C1—N2—C2—C3 | 1.5 (4) | C7—C8—C9—C10 | −2.1 (3) |
Li1—N2—C2—C3 | −159.1 (3) | C6—C5—C10—C9 | 1.4 (3) |
N2—C2—C3—C4 | −0.4 (4) | S1—C5—C10—C9 | −178.66 (17) |
C1—N3—C4—C3 | 1.2 (4) | C8—C9—C10—C5 | 0.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O2i | 0.88 (1) | 2.05 (2) | 2.881 (2) | 158 (3) |
O2W—H3W···N1ii | 0.87 (1) | 1.95 (2) | 2.805 (3) | 170 (4) |
O1W—H2W···N3ii | 0.87 (1) | 1.97 (1) | 2.837 (3) | 178 (3) |
O2W—H4W···N4iii | 0.86 (1) | 2.01 (1) | 2.866 (3) | 174 (4) |
N4—H1N···O2iv | 0.84 (3) | 2.40 (3) | 3.070 (3) | 137 (3) |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) x, −y, z−1/2; (iv) x+1/2, y−1/2, z. |
Poly[{µ
3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (II)
top
Crystal data top
[Na(C10H9N4O2S)] | F(000) = 560 |
Mr = 272.26 | Dx = 1.586 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.9010 (11) Å | Cell parameters from 2254 reflections |
b = 10.534 (4) Å | θ = 3.3–29.4° |
c = 18.389 (3) Å | µ = 0.32 mm−1 |
β = 94.216 (15)° | T = 123 K |
V = 1140.0 (5) Å3 | Rod, colourless |
Z = 4 | 0.35 × 0.12 × 0.08 mm |
Data collection top
Oxford Diffraction Xcalibur E diffractometer | 2351 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.029 |
ω scans | θmax = 29.5°, θmin = 3.5° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | h = −7→7 |
Tmin = 0.961, Tmax = 1.000 | k = −12→14 |
5903 measured reflections | l = −24→24 |
2786 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0278P)2 + 0.6871P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2786 reflections | Δρmax = 0.43 e Å−3 |
171 parameters | Δρmin = −0.46 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Na1 | 0.41732 (11) | −0.15699 (7) | 0.03430 (4) | 0.01483 (18) | |
S1 | 0.13569 (7) | 0.11080 (4) | 0.07836 (2) | 0.01030 (12) | |
O1 | 0.34050 (19) | 0.07207 (12) | 0.04443 (7) | 0.0130 (3) | |
O2 | 0.0133 (2) | 0.00644 (12) | 0.10838 (7) | 0.0152 (3) | |
N1 | −0.0383 (2) | 0.18774 (14) | 0.02732 (8) | 0.0121 (3) | |
N2 | 0.2445 (2) | 0.32085 (15) | −0.01969 (9) | 0.0154 (3) | |
N3 | −0.1495 (2) | 0.33011 (16) | −0.06053 (9) | 0.0155 (3) | |
N4 | 0.4138 (3) | 0.41926 (17) | 0.34001 (9) | 0.0182 (4) | |
C1 | 0.0271 (3) | 0.28102 (17) | −0.01786 (10) | 0.0122 (4) | |
C2 | 0.2788 (3) | 0.42162 (19) | −0.06182 (11) | 0.0197 (4) | |
H2 | 0.4295 | 0.4527 | −0.0633 | 0.024* | |
C3 | 0.1082 (3) | 0.4826 (2) | −0.10308 (12) | 0.0224 (4) | |
H3 | 0.1351 | 0.5566 | −0.1307 | 0.027* | |
C4 | −0.1042 (3) | 0.4292 (2) | −0.10165 (11) | 0.0198 (4) | |
H4 | −0.2252 | 0.4653 | −0.1318 | 0.024* | |
C5 | 0.2237 (3) | 0.20545 (17) | 0.15397 (10) | 0.0121 (4) | |
C6 | 0.0767 (3) | 0.21945 (18) | 0.20992 (10) | 0.0154 (4) | |
H6 | −0.0670 | 0.1783 | 0.2059 | 0.019* | |
C7 | 0.1368 (3) | 0.29163 (19) | 0.27051 (10) | 0.0162 (4) | |
H7 | 0.0348 | 0.3008 | 0.3078 | 0.019* | |
C8 | 0.3482 (3) | 0.35145 (18) | 0.27712 (10) | 0.0141 (4) | |
C9 | 0.4953 (3) | 0.33673 (19) | 0.22135 (11) | 0.0177 (4) | |
H9 | 0.6399 | 0.3768 | 0.2257 | 0.021* | |
C10 | 0.4342 (3) | 0.26494 (19) | 0.15998 (10) | 0.0160 (4) | |
H10 | 0.5352 | 0.2565 | 0.1224 | 0.019* | |
H1N | 0.301 (4) | 0.454 (2) | 0.3602 (13) | 0.023 (6)* | |
H2N | 0.528 (4) | 0.476 (2) | 0.3346 (13) | 0.029 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Na1 | 0.0126 (3) | 0.0166 (4) | 0.0152 (4) | −0.0003 (3) | 0.0003 (3) | 0.0012 (3) |
S1 | 0.0107 (2) | 0.0106 (2) | 0.0097 (2) | 0.00025 (15) | 0.00075 (15) | −0.00029 (17) |
O1 | 0.0130 (6) | 0.0136 (6) | 0.0126 (6) | 0.0030 (5) | 0.0020 (5) | −0.0009 (5) |
O2 | 0.0180 (6) | 0.0121 (6) | 0.0159 (7) | −0.0030 (5) | 0.0026 (5) | 0.0004 (6) |
N1 | 0.0107 (7) | 0.0137 (8) | 0.0118 (8) | 0.0004 (6) | −0.0005 (5) | 0.0013 (6) |
N2 | 0.0119 (7) | 0.0156 (8) | 0.0188 (8) | −0.0006 (6) | 0.0019 (6) | 0.0007 (7) |
N3 | 0.0126 (7) | 0.0173 (8) | 0.0163 (8) | 0.0029 (6) | −0.0002 (6) | 0.0032 (7) |
N4 | 0.0157 (8) | 0.0218 (9) | 0.0168 (9) | −0.0016 (7) | −0.0016 (6) | −0.0077 (7) |
C1 | 0.0116 (8) | 0.0136 (9) | 0.0114 (9) | 0.0017 (7) | 0.0013 (6) | −0.0022 (7) |
C2 | 0.0165 (9) | 0.0183 (10) | 0.0247 (11) | −0.0013 (7) | 0.0052 (7) | 0.0027 (9) |
C3 | 0.0243 (10) | 0.0171 (10) | 0.0267 (12) | 0.0027 (8) | 0.0084 (8) | 0.0075 (9) |
C4 | 0.0182 (9) | 0.0212 (10) | 0.0203 (10) | 0.0067 (8) | 0.0023 (7) | 0.0053 (9) |
C5 | 0.0123 (8) | 0.0131 (9) | 0.0106 (9) | 0.0017 (7) | −0.0014 (6) | 0.0002 (7) |
C6 | 0.0125 (8) | 0.0194 (10) | 0.0143 (9) | −0.0019 (7) | 0.0011 (7) | −0.0023 (8) |
C7 | 0.0132 (8) | 0.0212 (10) | 0.0145 (9) | −0.0003 (7) | 0.0027 (7) | −0.0021 (8) |
C8 | 0.0146 (8) | 0.0143 (9) | 0.0129 (9) | 0.0013 (7) | −0.0024 (7) | −0.0014 (8) |
C9 | 0.0131 (8) | 0.0223 (10) | 0.0174 (10) | −0.0041 (7) | −0.0010 (7) | −0.0024 (9) |
C10 | 0.0132 (8) | 0.0204 (10) | 0.0148 (9) | −0.0012 (7) | 0.0031 (7) | −0.0011 (8) |
Geometric parameters (Å, º) top
Na1—O1i | 2.2897 (15) | N4—C8 | 1.390 (2) |
Na1—N1ii | 2.4533 (15) | N4—Na1iv | 2.5772 (19) |
Na1—O1 | 2.4647 (17) | N4—H1N | 0.86 (2) |
Na1—N3ii | 2.4836 (18) | N4—H2N | 0.91 (2) |
Na1—N4iii | 2.5771 (19) | C1—Na1ii | 2.9255 (19) |
Na1—N2i | 2.6670 (17) | C2—C3 | 1.375 (3) |
Na1—C1ii | 2.9255 (19) | C2—H2 | 0.9500 |
Na1—Na1i | 3.6964 (19) | C3—C4 | 1.376 (3) |
S1—O2 | 1.4470 (14) | C3—H3 | 0.9500 |
S1—O1 | 1.4585 (13) | C4—H4 | 0.9500 |
S1—N1 | 1.5652 (15) | C5—C10 | 1.388 (2) |
S1—C5 | 1.7582 (18) | C5—C6 | 1.402 (2) |
O1—Na1i | 2.2897 (15) | C6—C7 | 1.374 (3) |
N1—C1 | 1.361 (2) | C6—H6 | 0.9500 |
N1—Na1ii | 2.4533 (15) | C7—C8 | 1.395 (2) |
N2—C2 | 1.338 (3) | C7—H7 | 0.9500 |
N2—C1 | 1.353 (2) | C8—C9 | 1.400 (3) |
N2—Na1i | 2.6670 (17) | C9—C10 | 1.384 (3) |
N3—C4 | 1.328 (3) | C9—H9 | 0.9500 |
N3—C1 | 1.360 (2) | C10—H10 | 0.9500 |
N3—Na1ii | 2.4836 (18) | | |
| | | |
O1i—Na1—N1ii | 110.47 (5) | C4—N3—C1 | 116.73 (16) |
O1i—Na1—O1 | 78.00 (5) | C4—N3—Na1ii | 147.74 (13) |
N1ii—Na1—O1 | 89.87 (5) | C1—N3—Na1ii | 94.60 (11) |
O1i—Na1—N3ii | 147.71 (6) | C8—N4—Na1iv | 130.68 (13) |
N1ii—Na1—N3ii | 54.64 (5) | C8—N4—H1N | 113.5 (15) |
O1—Na1—N3ii | 125.52 (6) | Na1iv—N4—H1N | 90.2 (15) |
O1i—Na1—N4iii | 103.13 (6) | C8—N4—H2N | 114.1 (15) |
N1ii—Na1—N4iii | 137.28 (6) | Na1iv—N4—H2N | 93.5 (15) |
O1—Na1—N4iii | 71.83 (5) | H1N—N4—H2N | 112 (2) |
N3ii—Na1—N4iii | 105.32 (6) | N2—C1—N3 | 123.76 (17) |
O1i—Na1—N2i | 71.51 (5) | N2—C1—N1 | 123.45 (15) |
N1ii—Na1—N2i | 122.11 (6) | N3—C1—N1 | 112.79 (15) |
O1—Na1—N2i | 141.66 (5) | N2—C1—Na1ii | 168.70 (13) |
N3ii—Na1—N2i | 92.06 (6) | N3—C1—Na1ii | 57.80 (9) |
N4iii—Na1—N2i | 92.82 (6) | N1—C1—Na1ii | 56.52 (8) |
O1i—Na1—C1ii | 134.88 (6) | N2—C2—C3 | 123.65 (17) |
N1ii—Na1—C1ii | 27.56 (5) | N2—C2—H2 | 118.2 |
O1—Na1—C1ii | 106.06 (5) | C3—C2—H2 | 118.2 |
N3ii—Na1—C1ii | 27.60 (5) | C2—C3—C4 | 115.45 (19) |
N4iii—Na1—C1ii | 121.09 (6) | C2—C3—H3 | 122.3 |
N2i—Na1—C1ii | 111.85 (6) | C4—C3—H3 | 122.3 |
O1i—Na1—Na1i | 40.71 (3) | N3—C4—C3 | 123.66 (18) |
N1ii—Na1—Na1i | 102.42 (5) | N3—C4—H4 | 118.2 |
O1—Na1—Na1i | 37.29 (4) | C3—C4—H4 | 118.2 |
N3ii—Na1—Na1i | 155.65 (5) | C10—C5—C6 | 119.51 (17) |
N4iii—Na1—Na1i | 86.15 (5) | C10—C5—S1 | 121.98 (14) |
N2i—Na1—Na1i | 109.06 (5) | C6—C5—S1 | 118.51 (13) |
C1ii—Na1—Na1i | 128.42 (5) | C7—C6—C5 | 121.10 (16) |
O2—S1—O1 | 113.78 (8) | C7—C6—H6 | 119.5 |
O2—S1—N1 | 107.35 (8) | C5—C6—H6 | 119.5 |
O1—S1—N1 | 114.59 (8) | C6—C7—C8 | 119.79 (17) |
O2—S1—C5 | 104.83 (8) | C6—C7—H7 | 120.1 |
O1—S1—C5 | 106.92 (8) | C8—C7—H7 | 120.1 |
N1—S1—C5 | 108.86 (8) | N4—C8—C7 | 119.84 (17) |
S1—O1—Na1i | 137.43 (8) | N4—C8—C9 | 121.08 (16) |
S1—O1—Na1 | 117.97 (7) | C7—C8—C9 | 119.01 (17) |
Na1i—O1—Na1 | 102.00 (5) | C10—C9—C8 | 121.26 (16) |
C1—N1—S1 | 122.48 (12) | C10—C9—H9 | 119.4 |
C1—N1—Na1ii | 95.92 (10) | C8—C9—H9 | 119.4 |
S1—N1—Na1ii | 138.08 (9) | C9—C10—C5 | 119.32 (17) |
C2—N2—C1 | 116.40 (15) | C9—C10—H10 | 120.3 |
C2—N2—Na1i | 107.99 (12) | C5—C10—H10 | 120.3 |
C1—N2—Na1i | 121.33 (12) | | |
| | | |
O2—S1—O1—Na1i | 163.45 (10) | Na1ii—N1—C1—N3 | 13.88 (16) |
N1—S1—O1—Na1i | 39.38 (14) | S1—N1—C1—Na1ii | 162.33 (16) |
C5—S1—O1—Na1i | −81.32 (12) | C1—N2—C2—C3 | −1.3 (3) |
O2—S1—O1—Na1 | 5.61 (10) | Na1i—N2—C2—C3 | 139.15 (18) |
N1—S1—O1—Na1 | −118.45 (8) | N2—C2—C3—C4 | −3.2 (3) |
C5—S1—O1—Na1 | 120.84 (8) | C1—N3—C4—C3 | 0.3 (3) |
O2—S1—N1—C1 | −170.13 (14) | Na1ii—N3—C4—C3 | −164.85 (18) |
O1—S1—N1—C1 | −42.71 (17) | C2—C3—C4—N3 | 3.8 (3) |
C5—S1—N1—C1 | 76.92 (16) | O2—S1—C5—C10 | 141.97 (15) |
O2—S1—N1—Na1ii | −17.00 (15) | O1—S1—C5—C10 | 20.87 (18) |
O1—S1—N1—Na1ii | 110.42 (13) | N1—S1—C5—C10 | −103.42 (16) |
C5—S1—N1—Na1ii | −129.95 (13) | O2—S1—C5—C6 | −37.32 (16) |
C2—N2—C1—N3 | 5.9 (3) | O1—S1—C5—C6 | −158.41 (14) |
Na1i—N2—C1—N3 | −128.95 (16) | N1—S1—C5—C6 | 77.29 (16) |
C2—N2—C1—N1 | −173.70 (18) | C10—C5—C6—C7 | 0.3 (3) |
Na1i—N2—C1—N1 | 51.4 (2) | S1—C5—C6—C7 | 179.62 (15) |
C2—N2—C1—Na1ii | 100.2 (7) | C5—C6—C7—C8 | −0.5 (3) |
Na1i—N2—C1—Na1ii | −34.7 (7) | Na1iv—N4—C8—C7 | 81.0 (2) |
C4—N3—C1—N2 | −5.4 (3) | Na1iv—N4—C8—C9 | −95.8 (2) |
Na1ii—N3—C1—N2 | 166.65 (16) | C6—C7—C8—N4 | −176.79 (18) |
C4—N3—C1—N1 | 174.24 (17) | C6—C7—C8—C9 | 0.1 (3) |
Na1ii—N3—C1—N1 | −13.67 (16) | N4—C8—C9—C10 | 177.32 (18) |
C4—N3—C1—Na1ii | −172.09 (19) | C7—C8—C9—C10 | 0.4 (3) |
S1—N1—C1—N2 | −4.1 (3) | C8—C9—C10—C5 | −0.6 (3) |
Na1ii—N1—C1—N2 | −166.45 (16) | C6—C5—C10—C9 | 0.2 (3) |
S1—N1—C1—N3 | 176.20 (13) | S1—C5—C10—C9 | −179.03 (15) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H1N···O2v | 0.86 (2) | 2.06 (2) | 2.907 (2) | 166 (2) |
N4—H2N···O1iv | 0.91 (2) | 2.52 (2) | 2.959 (2) | 110.5 (17) |
Symmetry codes: (iv) −x+1, y+1/2, −z+1/2; (v) −x, y+1/2, −z+1/2. |
Poly[diaqua{µ
3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}potassium(I)] (III)
top
Crystal data top
[K(C10H9N4O2S)(H2O)2] | Z = 4 |
Mr = 324.40 | F(000) = 672 |
Triclinic, P1 | Dx = 1.594 Mg m−3 |
a = 8.8503 (7) Å | Cu Kα radiation, λ = 1.5418 Å |
b = 9.6385 (4) Å | Cell parameters from 3605 reflections |
c = 15.9734 (7) Å | θ = 4.6–73.6° |
α = 92.350 (4)° | µ = 5.09 mm−1 |
β = 95.186 (4)° | T = 123 K |
γ = 94.209 (4)° | Block, colourless |
V = 1351.79 (13) Å3 | 0.28 × 0.15 × 0.10 mm |
Data collection top
Oxford Diffraction Gemini S diffractometer | 3951 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.050 |
ω scans | θmax = 73.8°, θmin = 4.6° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | h = −8→10 |
Tmin = 0.601, Tmax = 1.000 | k = −11→11 |
15580 measured reflections | l = −19→19 |
5357 independent reflections | |
Refinement top
Refinement on F2 | 14 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0619P)2 + 2.5308P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
5357 reflections | Δρmax = 0.81 e Å−3 |
404 parameters | Δρmin = −0.45 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
K1 | 0.24189 (11) | 0.55756 (9) | 0.47536 (6) | 0.0350 (2) | |
K2 | −0.15927 (12) | 0.82674 (9) | 0.41066 (6) | 0.0365 (2) | |
S1 | −0.26644 (12) | 0.67031 (10) | 0.19910 (6) | 0.0304 (2) | |
S2 | −0.05315 (12) | 0.81132 (10) | 0.61877 (6) | 0.0281 (2) | |
O1 | −0.3523 (3) | 0.6886 (3) | 0.27240 (19) | 0.0345 (7) | |
O2 | −0.3075 (4) | 0.7607 (3) | 0.1321 (2) | 0.0398 (7) | |
O1W | 0.4746 (5) | 0.4378 (5) | 0.5915 (3) | 0.0735 (14) | |
H1W | 0.450 (9) | 0.398 (6) | 0.637 (2) | 0.110* | |
H2W | 0.481 (10) | 0.362 (4) | 0.560 (4) | 0.110* | |
O3 | −0.0548 (3) | 0.9494 (3) | 0.58530 (18) | 0.0326 (7) | |
O2W | 0.2375 (5) | 0.8119 (4) | 0.3937 (2) | 0.0549 (10) | |
H3W | 0.196 (7) | 0.891 (4) | 0.398 (4) | 0.082* | |
H4W | 0.199 (7) | 0.785 (6) | 0.3424 (17) | 0.082* | |
O4 | −0.1743 (4) | 0.7140 (3) | 0.57871 (18) | 0.0346 (7) | |
O3W | −0.0485 (4) | 0.5553 (3) | 0.39403 (19) | 0.0359 (7) | |
H5W | −0.050 (6) | 0.584 (4) | 0.3428 (13) | 0.054* | |
H6W | −0.068 (6) | 0.4658 (13) | 0.384 (3) | 0.054* | |
O4W | −0.4475 (5) | 0.8724 (4) | 0.4641 (3) | 0.0604 (11) | |
H7W | −0.541 (3) | 0.843 (7) | 0.445 (4) | 0.091* | |
H8W | −0.466 (9) | 0.954 (7) | 0.486 (9) | 0.091* | 0.5 |
H9W | −0.436 (10) | 0.819 (11) | 0.507 (5) | 0.091* | 0.5 |
N1 | −0.0933 (4) | 0.6879 (3) | 0.2369 (2) | 0.0301 (8) | |
N2 | 0.1612 (4) | 0.7098 (4) | 0.2256 (2) | 0.0342 (8) | |
N3 | −0.0068 (4) | 0.6541 (4) | 0.1017 (2) | 0.0348 (8) | |
N4 | −0.4201 (6) | 0.0807 (5) | 0.0779 (3) | 0.0504 (12) | |
N5 | 0.0982 (4) | 0.7389 (4) | 0.6097 (2) | 0.0317 (8) | |
N6 | 0.2546 (4) | 0.9310 (3) | 0.6755 (2) | 0.0303 (8) | |
N7 | 0.3546 (5) | 0.7193 (4) | 0.6308 (2) | 0.0384 (9) | |
N8 | −0.1718 (6) | 0.8726 (5) | 0.9774 (3) | 0.0441 (10) | |
C1 | 0.0218 (5) | 0.6828 (4) | 0.1849 (3) | 0.0309 (9) | |
C2 | 0.2782 (6) | 0.7163 (5) | 0.1785 (3) | 0.0433 (11) | |
H2 | 0.3781 | 0.7352 | 0.2055 | 0.052* | |
C3 | 0.2599 (6) | 0.6967 (5) | 0.0925 (3) | 0.0447 (12) | |
H3 | 0.3436 | 0.7068 | 0.0593 | 0.054* | |
C4 | 0.1144 (6) | 0.6617 (5) | 0.0567 (3) | 0.0406 (11) | |
H4 | 0.0987 | 0.6421 | −0.0023 | 0.049* | |
C5 | −0.3070 (5) | 0.4959 (4) | 0.1601 (3) | 0.0299 (9) | |
C6 | −0.2140 (5) | 0.3935 (4) | 0.1847 (3) | 0.0312 (9) | |
H6 | −0.1236 | 0.4172 | 0.2207 | 0.037* | |
C7 | −0.2516 (5) | 0.2566 (5) | 0.1571 (3) | 0.0353 (10) | |
H7 | −0.1851 | 0.1873 | 0.1732 | 0.042* | |
C8 | −0.3841 (5) | 0.2186 (5) | 0.1065 (3) | 0.0377 (11) | |
C9 | −0.4762 (6) | 0.3219 (6) | 0.0812 (3) | 0.0480 (13) | |
H9 | −0.5667 | 0.2978 | 0.0453 | 0.058* | |
C10 | −0.4386 (5) | 0.4598 (5) | 0.1073 (3) | 0.0436 (12) | |
H10 | −0.5028 | 0.5297 | 0.0892 | 0.052* | |
C11 | 0.2388 (5) | 0.8013 (4) | 0.6399 (3) | 0.0295 (9) | |
C12 | 0.3946 (5) | 0.9760 (4) | 0.7084 (3) | 0.0339 (10) | |
H12 | 0.4095 | 1.0670 | 0.7344 | 0.041* | |
C13 | 0.5188 (5) | 0.8976 (5) | 0.7068 (3) | 0.0384 (10) | |
H13 | 0.6166 | 0.9299 | 0.7326 | 0.046* | |
C14 | 0.4908 (6) | 0.7693 (5) | 0.6650 (3) | 0.0428 (11) | |
H14 | 0.5740 | 0.7133 | 0.6603 | 0.051* | |
C15 | −0.0866 (5) | 0.8295 (4) | 0.7260 (2) | 0.0269 (8) | |
C16 | −0.1369 (5) | 0.7129 (4) | 0.7677 (3) | 0.0298 (9) | |
H16 | −0.1542 | 0.6246 | 0.7382 | 0.036* | |
C17 | −0.1615 (5) | 0.7256 (4) | 0.8511 (3) | 0.0334 (10) | |
H17 | −0.1935 | 0.6454 | 0.8794 | 0.040* | |
C18 | −0.1399 (5) | 0.8561 (4) | 0.8955 (3) | 0.0313 (9) | |
C19 | −0.0884 (5) | 0.9708 (4) | 0.8523 (3) | 0.0300 (9) | |
H19 | −0.0723 | 1.0597 | 0.8810 | 0.036* | |
C20 | −0.0605 (5) | 0.9583 (4) | 0.7689 (3) | 0.0281 (9) | |
H20 | −0.0236 | 1.0373 | 0.7410 | 0.034* | |
H1N | −0.515 (8) | 0.057 (7) | 0.059 (4) | 0.07 (2)* | |
H2N | −0.383 (7) | 0.010 (7) | 0.111 (4) | 0.06 (2)* | |
H3N | −0.185 (6) | 0.800 (5) | 1.008 (3) | 0.037 (14)* | |
H4N | −0.156 (6) | 0.955 (6) | 1.004 (3) | 0.053 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
K1 | 0.0413 (5) | 0.0269 (5) | 0.0355 (5) | −0.0036 (4) | 0.0044 (4) | −0.0060 (4) |
K2 | 0.0504 (6) | 0.0234 (4) | 0.0337 (5) | −0.0016 (4) | −0.0020 (4) | −0.0007 (3) |
S1 | 0.0337 (6) | 0.0274 (5) | 0.0301 (5) | 0.0045 (4) | 0.0037 (4) | −0.0023 (4) |
S2 | 0.0327 (5) | 0.0236 (5) | 0.0269 (5) | −0.0012 (4) | 0.0021 (4) | −0.0022 (4) |
O1 | 0.0344 (17) | 0.0338 (16) | 0.0354 (16) | 0.0017 (13) | 0.0071 (13) | −0.0064 (13) |
O2 | 0.046 (2) | 0.0372 (17) | 0.0375 (17) | 0.0119 (14) | 0.0050 (14) | 0.0017 (13) |
O1W | 0.048 (2) | 0.079 (3) | 0.100 (4) | 0.009 (2) | 0.018 (2) | 0.049 (3) |
O3 | 0.0342 (17) | 0.0296 (15) | 0.0339 (16) | 0.0023 (13) | 0.0021 (12) | 0.0019 (12) |
O2W | 0.077 (3) | 0.0357 (19) | 0.050 (2) | 0.0102 (19) | −0.0048 (19) | −0.0027 (16) |
O4 | 0.0381 (17) | 0.0325 (16) | 0.0310 (15) | −0.0049 (13) | 0.0005 (13) | −0.0043 (12) |
O3W | 0.0464 (19) | 0.0274 (15) | 0.0330 (16) | 0.0014 (14) | 0.0028 (14) | −0.0039 (12) |
O4W | 0.079 (3) | 0.039 (2) | 0.067 (3) | 0.0007 (19) | 0.031 (2) | 0.0003 (18) |
N1 | 0.036 (2) | 0.0247 (17) | 0.0286 (18) | −0.0033 (15) | 0.0060 (15) | −0.0011 (14) |
N2 | 0.033 (2) | 0.0271 (18) | 0.043 (2) | 0.0030 (15) | 0.0090 (16) | 0.0011 (15) |
N3 | 0.045 (2) | 0.0241 (18) | 0.036 (2) | 0.0029 (16) | 0.0113 (17) | −0.0007 (15) |
N4 | 0.057 (3) | 0.045 (3) | 0.045 (3) | −0.017 (2) | 0.010 (2) | −0.020 (2) |
N5 | 0.040 (2) | 0.0240 (17) | 0.0315 (19) | 0.0023 (15) | 0.0070 (15) | −0.0046 (14) |
N6 | 0.033 (2) | 0.0240 (17) | 0.0340 (19) | −0.0005 (14) | 0.0040 (15) | −0.0004 (14) |
N7 | 0.045 (2) | 0.034 (2) | 0.037 (2) | 0.0081 (17) | 0.0049 (17) | −0.0048 (16) |
N8 | 0.071 (3) | 0.031 (2) | 0.031 (2) | −0.002 (2) | 0.0101 (19) | −0.0008 (17) |
C1 | 0.038 (2) | 0.0164 (19) | 0.039 (2) | 0.0026 (17) | 0.0089 (19) | 0.0003 (16) |
C2 | 0.035 (3) | 0.033 (2) | 0.064 (3) | 0.007 (2) | 0.012 (2) | 0.010 (2) |
C3 | 0.043 (3) | 0.041 (3) | 0.057 (3) | 0.015 (2) | 0.023 (2) | 0.011 (2) |
C4 | 0.059 (3) | 0.029 (2) | 0.038 (2) | 0.009 (2) | 0.017 (2) | 0.0040 (18) |
C5 | 0.028 (2) | 0.032 (2) | 0.029 (2) | 0.0021 (17) | 0.0035 (16) | −0.0066 (17) |
C6 | 0.032 (2) | 0.029 (2) | 0.031 (2) | 0.0000 (18) | −0.0012 (17) | −0.0006 (17) |
C7 | 0.043 (3) | 0.030 (2) | 0.033 (2) | 0.0007 (19) | 0.0027 (19) | −0.0010 (17) |
C8 | 0.037 (3) | 0.040 (2) | 0.035 (2) | −0.008 (2) | 0.0099 (19) | −0.0118 (19) |
C9 | 0.031 (3) | 0.060 (3) | 0.048 (3) | −0.004 (2) | −0.002 (2) | −0.028 (2) |
C10 | 0.030 (2) | 0.054 (3) | 0.046 (3) | 0.016 (2) | −0.004 (2) | −0.017 (2) |
C11 | 0.035 (2) | 0.027 (2) | 0.028 (2) | 0.0019 (17) | 0.0058 (17) | 0.0002 (16) |
C12 | 0.036 (2) | 0.028 (2) | 0.037 (2) | −0.0023 (18) | 0.0018 (19) | −0.0017 (17) |
C13 | 0.023 (2) | 0.047 (3) | 0.044 (3) | 0.0054 (19) | −0.0007 (18) | −0.001 (2) |
C14 | 0.036 (3) | 0.052 (3) | 0.042 (3) | 0.018 (2) | 0.004 (2) | 0.000 (2) |
C15 | 0.028 (2) | 0.026 (2) | 0.027 (2) | 0.0014 (16) | 0.0041 (16) | −0.0019 (15) |
C16 | 0.030 (2) | 0.022 (2) | 0.036 (2) | 0.0004 (16) | 0.0022 (17) | −0.0044 (16) |
C17 | 0.037 (2) | 0.022 (2) | 0.041 (2) | −0.0012 (18) | 0.0028 (19) | 0.0044 (17) |
C18 | 0.030 (2) | 0.031 (2) | 0.032 (2) | 0.0013 (18) | 0.0016 (17) | −0.0023 (17) |
C19 | 0.029 (2) | 0.023 (2) | 0.036 (2) | 0.0024 (17) | 0.0001 (17) | −0.0061 (16) |
C20 | 0.025 (2) | 0.0224 (19) | 0.036 (2) | 0.0003 (16) | 0.0016 (16) | 0.0004 (16) |
Geometric parameters (Å, º) top
K1—O4i | 2.729 (3) | N1—C1 | 1.373 (5) |
K1—O3W | 2.771 (3) | N2—C2 | 1.333 (6) |
K1—O1Wii | 2.812 (5) | N2—C1 | 1.343 (6) |
K1—O2W | 2.824 (4) | N3—C4 | 1.343 (6) |
K1—N7 | 2.932 (4) | N3—C1 | 1.344 (6) |
K1—O1W | 2.975 (5) | N4—C8 | 1.393 (6) |
K1—O3Wi | 3.004 (3) | N4—H1N | 0.87 (7) |
K1—N5 | 3.129 (4) | N4—H2N | 0.93 (7) |
K1—C11 | 3.457 (4) | N5—C11 | 1.379 (5) |
K1—K2i | 4.2385 (13) | N6—C12 | 1.336 (6) |
K1—K1i | 4.491 (2) | N6—C11 | 1.344 (5) |
K1—K2 | 4.6167 (15) | N6—K2iii | 2.899 (4) |
K1—H6W | 3.04 (5) | N7—C14 | 1.325 (6) |
K2—O3iii | 2.759 (3) | N7—C11 | 1.355 (6) |
K2—O4W | 2.820 (4) | N8—C18 | 1.369 (6) |
K2—O3W | 2.871 (3) | N8—H3N | 0.87 (5) |
K2—O1 | 2.883 (3) | N8—H4N | 0.88 (6) |
K2—N6iii | 2.899 (4) | C2—C3 | 1.372 (7) |
K2—O4 | 2.947 (3) | C2—H2 | 0.9500 |
K2—O3 | 3.023 (3) | C3—C4 | 1.373 (7) |
K2—N1 | 3.153 (3) | C3—H3 | 0.9500 |
K2—S2 | 3.3840 (14) | C4—H4 | 0.9500 |
K2—C12iii | 3.425 (5) | C5—C6 | 1.378 (6) |
K2—S1 | 3.6587 (14) | C5—C10 | 1.388 (6) |
K2—K1i | 4.2385 (13) | C6—C7 | 1.382 (6) |
K2—H5W | 2.81 (5) | C6—H6 | 0.9500 |
K2—H9W | 3.01 (11) | C7—C8 | 1.379 (6) |
S1—O2 | 1.445 (3) | C7—H7 | 0.9500 |
S1—O1 | 1.464 (3) | C8—C9 | 1.383 (7) |
S1—N1 | 1.589 (4) | C9—C10 | 1.385 (7) |
S1—C5 | 1.769 (4) | C9—H9 | 0.9500 |
S2—O3 | 1.455 (3) | C10—H10 | 0.9500 |
S2—O4 | 1.455 (3) | C12—C13 | 1.380 (6) |
S2—N5 | 1.570 (4) | C12—K2iii | 3.425 (5) |
S2—C15 | 1.768 (4) | C12—H12 | 0.9500 |
O1W—K1ii | 2.812 (5) | C13—C14 | 1.376 (7) |
O1W—H1W | 0.880 (10) | C13—H13 | 0.9500 |
O1W—H2W | 0.877 (10) | C14—H14 | 0.9500 |
O3—K2iii | 2.759 (3) | C15—C20 | 1.387 (5) |
O2W—H3W | 0.878 (10) | C15—C16 | 1.395 (6) |
O2W—H4W | 0.880 (10) | C16—C17 | 1.372 (6) |
O4—K1i | 2.729 (3) | C16—H16 | 0.9500 |
O3W—K1i | 3.004 (3) | C17—C18 | 1.410 (6) |
O3W—H5W | 0.874 (10) | C17—H17 | 0.9500 |
O3W—H6W | 0.873 (10) | C18—C19 | 1.397 (6) |
O4W—H7W | 0.878 (10) | C19—C20 | 1.378 (6) |
O4W—H8W | 0.879 (10) | C19—H19 | 0.9500 |
O4W—H9W | 0.878 (10) | C20—H20 | 0.9500 |
| | | |
O4i—K1—O3W | 76.14 (9) | C12iii—K2—H5W | 121.5 (6) |
O4i—K1—O1Wii | 91.40 (13) | S1—K2—H5W | 54.1 (7) |
O3W—K1—O1Wii | 129.93 (13) | K1i—K2—H5W | 60.3 (5) |
O4i—K1—O2W | 133.37 (10) | O3iii—K2—H9W | 124 (2) |
O3W—K1—O2W | 75.00 (11) | O4W—K2—H9W | 17.0 (8) |
O1Wii—K1—O2W | 80.19 (13) | O3W—K2—H9W | 111.2 (19) |
O4i—K1—N7 | 138.88 (11) | O1—K2—H9W | 87.0 (19) |
O3W—K1—N7 | 125.77 (11) | N6iii—K2—H9W | 91.0 (12) |
O1Wii—K1—N7 | 95.36 (15) | O4—K2—H9W | 55.4 (6) |
O2W—K1—N7 | 87.72 (11) | O3—K2—H9W | 73.4 (18) |
O4i—K1—O1W | 83.27 (12) | N1—K2—H9W | 133 (2) |
O3W—K1—O1W | 152.02 (11) | S2—K2—H9W | 70.2 (11) |
O1Wii—K1—O1W | 68.49 (15) | C12iii—K2—H9W | 78.2 (7) |
O2W—K1—O1W | 132.73 (12) | S1—K2—H9W | 109.0 (18) |
N7—K1—O1W | 62.11 (14) | K1i—K2—H9W | 67.2 (16) |
O4i—K1—O3Wi | 76.90 (9) | H5W—K2—H9W | 122 (2) |
O3W—K1—O3Wi | 78.00 (10) | O2—S1—O1 | 113.35 (19) |
O1Wii—K1—O3Wi | 146.61 (12) | O2—S1—N1 | 115.66 (19) |
O2W—K1—O3Wi | 130.21 (12) | O1—S1—N1 | 104.21 (18) |
N7—K1—O3Wi | 75.36 (10) | O2—S1—C5 | 108.1 (2) |
O1W—K1—O3Wi | 79.04 (11) | O1—S1—C5 | 107.12 (18) |
O4i—K1—N5 | 130.33 (10) | N1—S1—C5 | 107.9 (2) |
O3W—K1—N5 | 81.94 (10) | O2—S1—K2 | 118.44 (13) |
O1Wii—K1—N5 | 135.34 (13) | O1—S1—K2 | 47.64 (12) |
O2W—K1—N5 | 80.19 (11) | N1—S1—K2 | 59.11 (13) |
N7—K1—N5 | 44.19 (10) | C5—S1—K2 | 132.72 (15) |
O1W—K1—N5 | 97.70 (13) | O3—S2—O4 | 112.95 (18) |
O3Wi—K1—N5 | 55.02 (9) | O3—S2—N5 | 114.45 (19) |
O4i—K1—C11 | 145.79 (10) | O4—S2—N5 | 105.51 (19) |
O3W—K1—C11 | 103.38 (10) | O3—S2—C15 | 106.97 (18) |
O1Wii—K1—C11 | 112.40 (14) | O4—S2—C15 | 106.49 (18) |
O2W—K1—C11 | 76.90 (10) | N5—S2—C15 | 110.2 (2) |
N7—K1—C11 | 22.63 (11) | O3—S2—K2 | 63.26 (12) |
O1W—K1—C11 | 83.25 (13) | O4—S2—K2 | 60.28 (12) |
O3Wi—K1—C11 | 69.73 (9) | N5—S2—K2 | 97.00 (14) |
N5—K1—C11 | 23.50 (10) | C15—S2—K2 | 152.44 (15) |
O4i—K1—K2i | 43.70 (6) | S1—O1—K2 | 110.33 (15) |
O3W—K1—K2i | 94.71 (7) | K1ii—O1W—K1 | 111.51 (15) |
O1Wii—K1—K2i | 109.14 (9) | K1ii—O1W—H1W | 126 (5) |
O2W—K1—K2i | 169.33 (10) | K1—O1W—H1W | 122 (6) |
N7—K1—K2i | 96.31 (8) | K1ii—O1W—H2W | 69 (6) |
O1W—K1—K2i | 57.39 (8) | K1—O1W—H2W | 96 (6) |
O3Wi—K1—K2i | 42.59 (6) | H1W—O1W—H2W | 98 (2) |
N5—K1—K2i | 95.81 (7) | S2—O3—K2iii | 133.47 (17) |
C11—K1—K2i | 103.32 (7) | S2—O3—K2 | 91.28 (13) |
O4i—K1—K1i | 72.58 (7) | K2iii—O3—K2 | 114.35 (10) |
O3W—K1—K1i | 40.87 (7) | K1—O2W—H3W | 139 (4) |
O1Wii—K1—K1i | 162.68 (12) | K1—O2W—H4W | 102 (4) |
O2W—K1—K1i | 105.79 (10) | H3W—O2W—H4W | 99 (2) |
N7—K1—K1i | 101.05 (9) | S2—O4—K1i | 143.3 (2) |
O1W—K1—K1i | 114.70 (9) | S2—O4—K2 | 94.33 (14) |
O3Wi—K1—K1i | 37.13 (6) | K1i—O4—K2 | 96.54 (9) |
N5—K1—K1i | 61.97 (7) | K1—O3W—K2 | 109.81 (10) |
C11—K1—K1i | 84.90 (8) | K1—O3W—K1i | 102.00 (10) |
K2i—K1—K1i | 63.78 (3) | K2—O3W—K1i | 92.33 (9) |
O4i—K1—K2 | 111.87 (7) | K1—O3W—H5W | 114 (4) |
O3W—K1—K2 | 35.80 (6) | K2—O3W—H5W | 77 (3) |
O1Wii—K1—K2 | 128.87 (9) | K1i—O3W—H5W | 144 (4) |
O2W—K1—K2 | 50.39 (10) | K1—O3W—H6W | 99 (4) |
N7—K1—K2 | 94.90 (8) | K2—O3W—H6W | 149 (4) |
O1W—K1—K2 | 154.32 (11) | K1i—O3W—H6W | 71 (3) |
O3Wi—K1—K2 | 84.29 (7) | H5W—O3W—H6W | 101 (2) |
N5—K1—K2 | 56.63 (7) | K2—O4W—H7W | 134 (5) |
C11—K1—K2 | 72.66 (8) | K2—O4W—H8W | 121 (7) |
K2i—K1—K2 | 119.23 (3) | H7W—O4W—H8W | 99 (2) |
K1i—K1—K2 | 55.45 (3) | K2—O4W—H9W | 94 (8) |
O4i—K1—H6W | 59.8 (5) | H7W—O4W—H9W | 99 (2) |
O3W—K1—H6W | 16.5 (5) | C1—N1—S1 | 120.6 (3) |
O1Wii—K1—H6W | 127.1 (9) | C1—N1—K2 | 139.9 (3) |
O2W—K1—H6W | 89.3 (5) | S1—N1—K2 | 95.26 (15) |
N7—K1—H6W | 136.2 (8) | C2—N2—C1 | 116.9 (4) |
O1W—K1—H6W | 137.8 (5) | C4—N3—C1 | 116.1 (4) |
O3Wi—K1—H6W | 73.6 (8) | C8—N4—H1N | 117 (4) |
N5—K1—H6W | 92.3 (8) | C8—N4—H2N | 118 (4) |
C11—K1—H6W | 115.3 (8) | H1N—N4—H2N | 110 (6) |
K2i—K1—H6W | 80.9 (6) | C11—N5—S2 | 122.3 (3) |
K1i—K1—H6W | 38.7 (9) | C11—N5—K1 | 91.7 (2) |
K2—K1—H6W | 52.1 (5) | S2—N5—K1 | 138.42 (19) |
O3iii—K2—O4W | 118.31 (10) | C12—N6—C11 | 116.1 (4) |
O3iii—K2—O3W | 116.43 (10) | C12—N6—K2iii | 101.5 (3) |
O4W—K2—O3W | 123.26 (11) | C11—N6—K2iii | 123.5 (3) |
O3iii—K2—O1 | 130.90 (9) | C14—N7—C11 | 116.3 (4) |
O4W—K2—O1 | 80.08 (11) | C14—N7—K1 | 134.6 (3) |
O3W—K2—O1 | 75.53 (9) | C11—N7—K1 | 101.0 (3) |
O3iii—K2—N6iii | 63.92 (9) | C18—N8—H3N | 121 (3) |
O4W—K2—N6iii | 74.67 (11) | C18—N8—H4N | 120 (4) |
O3W—K2—N6iii | 146.26 (10) | H3N—N8—H4N | 117 (5) |
O1—K2—N6iii | 80.79 (10) | N2—C1—N3 | 124.9 (4) |
O3iii—K2—O4 | 111.22 (9) | N2—C1—N1 | 113.4 (4) |
O4W—K2—O4 | 72.00 (12) | N3—C1—N1 | 121.7 (4) |
O3W—K2—O4 | 75.72 (9) | N2—C2—C3 | 122.6 (5) |
O1—K2—O4 | 117.84 (9) | N2—C2—H2 | 118.7 |
N6iii—K2—O4 | 137.47 (10) | C3—C2—H2 | 118.7 |
O3iii—K2—O3 | 65.65 (10) | C2—C3—C4 | 116.6 (4) |
O4W—K2—O3 | 81.82 (11) | C2—C3—H3 | 121.7 |
O3W—K2—O3 | 108.46 (9) | C4—C3—H3 | 121.7 |
O1—K2—O3 | 160.24 (9) | N3—C4—C3 | 122.8 (5) |
N6iii—K2—O3 | 101.97 (9) | N3—C4—H4 | 118.6 |
O4—K2—O3 | 47.93 (8) | C3—C4—H4 | 118.6 |
O3iii—K2—N1 | 97.57 (9) | C6—C5—C10 | 119.2 (4) |
O4W—K2—N1 | 126.61 (12) | C6—C5—S1 | 121.0 (3) |
O3W—K2—N1 | 56.72 (9) | C10—C5—S1 | 119.7 (4) |
O1—K2—N1 | 46.81 (9) | C5—C6—C7 | 120.2 (4) |
N6iii—K2—N1 | 89.55 (10) | C5—C6—H6 | 119.9 |
O4—K2—N1 | 131.79 (9) | C7—C6—H6 | 119.9 |
O3—K2—N1 | 151.48 (10) | C8—C7—C6 | 121.2 (5) |
O3iii—K2—S2 | 85.85 (7) | C8—C7—H7 | 119.4 |
O4W—K2—S2 | 84.25 (10) | C6—C7—H7 | 119.4 |
O3W—K2—S2 | 85.87 (7) | C7—C8—C9 | 118.4 (4) |
O1—K2—S2 | 143.14 (7) | C7—C8—N4 | 120.9 (5) |
N6iii—K2—S2 | 126.55 (7) | C9—C8—N4 | 120.7 (5) |
O4—K2—S2 | 25.39 (6) | C8—C9—C10 | 121.0 (4) |
O3—K2—S2 | 25.46 (6) | C8—C9—H9 | 119.5 |
N1—K2—S2 | 139.86 (8) | C10—C9—H9 | 119.5 |
O3iii—K2—C12iii | 86.35 (10) | C9—C10—C5 | 119.9 (5) |
O4W—K2—C12iii | 61.29 (12) | C9—C10—H10 | 120.1 |
O3W—K2—C12iii | 136.33 (10) | C5—C10—H10 | 120.1 |
O1—K2—C12iii | 62.11 (10) | N6—C11—N7 | 124.8 (4) |
N6iii—K2—C12iii | 22.46 (10) | N6—C11—N5 | 121.6 (4) |
O4—K2—C12iii | 132.77 (10) | N7—C11—N5 | 113.6 (4) |
O3—K2—C12iii | 114.98 (9) | N6—C11—K1 | 154.2 (3) |
N1—K2—C12iii | 85.10 (10) | N7—C11—K1 | 56.4 (2) |
S2—K2—C12iii | 135.02 (8) | N5—C11—K1 | 64.8 (2) |
O3iii—K2—S1 | 113.47 (7) | N6—C12—C13 | 123.7 (4) |
O4W—K2—S1 | 101.02 (10) | N6—C12—K2iii | 56.0 (2) |
O3W—K2—S1 | 69.16 (7) | C13—C12—K2iii | 143.9 (3) |
O1—K2—S1 | 22.03 (6) | N6—C12—H12 | 118.2 |
N6iii—K2—S1 | 79.88 (7) | C13—C12—H12 | 118.2 |
O4—K2—S1 | 131.84 (6) | K2iii—C12—H12 | 74.7 |
O3—K2—S1 | 176.98 (7) | C14—C13—C12 | 115.2 (4) |
N1—K2—S1 | 25.63 (7) | C14—C13—H13 | 122.4 |
S2—K2—S1 | 153.19 (4) | C12—C13—H13 | 122.4 |
C12iii—K2—S1 | 67.56 (8) | N7—C14—C13 | 123.8 (5) |
O3iii—K2—K1i | 140.99 (7) | N7—C14—H14 | 118.1 |
O4W—K2—K1i | 81.88 (9) | C13—C14—H14 | 118.1 |
O3W—K2—K1i | 45.08 (7) | C20—C15—C16 | 120.1 (4) |
O1—K2—K1i | 82.84 (7) | C20—C15—S2 | 120.3 (3) |
N6iii—K2—K1i | 153.33 (8) | C16—C15—S2 | 119.6 (3) |
O4—K2—K1i | 39.76 (6) | C17—C16—C15 | 120.0 (4) |
O3—K2—K1i | 86.84 (6) | C17—C16—H16 | 120.0 |
N1—K2—K1i | 94.45 (7) | C15—C16—H16 | 120.0 |
S2—K2—K1i | 61.95 (3) | C16—C17—C18 | 121.0 (4) |
C12iii—K2—K1i | 131.72 (8) | C16—C17—H17 | 119.5 |
S1—K2—K1i | 92.52 (3) | C18—C17—H17 | 119.5 |
O3iii—K2—H5W | 111.4 (10) | N8—C18—C19 | 120.3 (4) |
O4W—K2—H5W | 130.2 (11) | N8—C18—C17 | 121.9 (4) |
O3W—K2—H5W | 17.7 (2) | C19—C18—C17 | 117.7 (4) |
O1—K2—H5W | 65.1 (9) | C20—C19—C18 | 121.6 (4) |
N6iii—K2—H5W | 128.6 (3) | C20—C19—H19 | 119.2 |
O4—K2—H5W | 93.3 (2) | C18—C19—H19 | 119.2 |
O3—K2—H5W | 123.2 (7) | C19—C20—C15 | 119.5 (4) |
N1—K2—H5W | 39.1 (3) | C19—C20—H20 | 120.2 |
S2—K2—H5W | 102.5 (4) | C15—C20—H20 | 120.2 |
| | | |
O2—S1—O1—K2 | −107.96 (19) | C10—C5—C6—C7 | 0.0 (7) |
N1—S1—O1—K2 | 18.6 (2) | S1—C5—C6—C7 | 176.6 (3) |
C5—S1—O1—K2 | 132.83 (18) | C5—C6—C7—C8 | −1.8 (7) |
O4—S2—O3—K2iii | −161.4 (2) | C6—C7—C8—C9 | 2.5 (7) |
N5—S2—O3—K2iii | −40.7 (3) | C6—C7—C8—N4 | 179.0 (4) |
C15—S2—O3—K2iii | 81.7 (3) | C7—C8—C9—C10 | −1.4 (7) |
K2—S2—O3—K2iii | −126.1 (2) | N4—C8—C9—C10 | −178.0 (5) |
O4—S2—O3—K2 | −35.30 (18) | C8—C9—C10—C5 | −0.3 (8) |
N5—S2—O3—K2 | 85.46 (17) | C6—C5—C10—C9 | 1.0 (7) |
C15—S2—O3—K2 | −152.14 (15) | S1—C5—C10—C9 | −175.6 (4) |
O3—S2—O4—K1i | 143.5 (3) | C12—N6—C11—N7 | −4.4 (6) |
N5—S2—O4—K1i | 17.7 (3) | K2iii—N6—C11—N7 | 121.7 (4) |
C15—S2—O4—K1i | −99.4 (3) | C12—N6—C11—N5 | 174.9 (4) |
K2—S2—O4—K1i | 107.0 (3) | K2iii—N6—C11—N5 | −59.0 (5) |
O3—S2—O4—K2 | 36.46 (19) | C12—N6—C11—K1 | −88.0 (7) |
N5—S2—O4—K2 | −89.27 (17) | K2iii—N6—C11—K1 | 38.2 (8) |
C15—S2—O4—K2 | 153.58 (16) | C14—N7—C11—N6 | 4.7 (7) |
O2—S1—N1—C1 | −52.2 (4) | K1—N7—C11—N6 | −148.8 (4) |
O1—S1—N1—C1 | −177.3 (3) | C14—N7—C11—N5 | −174.6 (4) |
C5—S1—N1—C1 | 69.1 (3) | K1—N7—C11—N5 | 32.0 (4) |
K2—S1—N1—C1 | −161.3 (4) | C14—N7—C11—K1 | 153.4 (5) |
O2—S1—N1—K2 | 109.16 (17) | S2—N5—C11—N6 | −3.2 (6) |
O1—S1—N1—K2 | −15.96 (17) | K1—N5—C11—N6 | 151.5 (4) |
C5—S1—N1—K2 | −129.60 (16) | S2—N5—C11—N7 | 176.2 (3) |
O3—S2—N5—C11 | 54.6 (4) | K1—N5—C11—N7 | −29.2 (4) |
O4—S2—N5—C11 | 179.4 (3) | S2—N5—C11—K1 | −154.7 (3) |
C15—S2—N5—C11 | −66.0 (4) | C11—N6—C12—C13 | 0.4 (6) |
K2—S2—N5—C11 | 118.3 (3) | K2iii—N6—C12—C13 | −136.1 (4) |
O3—S2—N5—K1 | −85.3 (3) | C11—N6—C12—K2iii | 136.5 (4) |
O4—S2—N5—K1 | 39.5 (3) | N6—C12—C13—C14 | 2.8 (7) |
C15—S2—N5—K1 | 154.1 (2) | K2iii—C12—C13—C14 | −74.1 (7) |
K2—S2—N5—K1 | −21.6 (3) | C11—N7—C14—C13 | −1.0 (7) |
C2—N2—C1—N3 | 4.1 (6) | K1—N7—C14—C13 | 140.9 (4) |
C2—N2—C1—N1 | −175.5 (4) | C12—C13—C14—N7 | −2.5 (7) |
C4—N3—C1—N2 | −4.1 (6) | O3—S2—C15—C20 | −20.6 (4) |
C4—N3—C1—N1 | 175.5 (4) | O4—S2—C15—C20 | −141.6 (3) |
S1—N1—C1—N2 | 175.3 (3) | N5—S2—C15—C20 | 104.4 (4) |
K2—N1—C1—N2 | 25.0 (6) | K2—S2—C15—C20 | −85.0 (4) |
S1—N1—C1—N3 | −4.4 (5) | O3—S2—C15—C16 | 160.5 (3) |
K2—N1—C1—N3 | −154.7 (3) | O4—S2—C15—C16 | 39.5 (4) |
C1—N2—C2—C3 | 0.0 (7) | N5—S2—C15—C16 | −74.4 (4) |
N2—C2—C3—C4 | −3.6 (7) | K2—S2—C15—C16 | 96.1 (4) |
C1—N3—C4—C3 | −0.1 (6) | C20—C15—C16—C17 | 0.4 (6) |
C2—C3—C4—N3 | 3.7 (7) | S2—C15—C16—C17 | 179.2 (3) |
O2—S1—C5—C6 | 143.5 (4) | C15—C16—C17—C18 | 1.4 (7) |
O1—S1—C5—C6 | −94.0 (4) | C16—C17—C18—N8 | 176.3 (4) |
N1—S1—C5—C6 | 17.7 (4) | C16—C17—C18—C19 | −1.8 (7) |
K2—S1—C5—C6 | −46.4 (4) | N8—C18—C19—C20 | −177.7 (4) |
O2—S1—C5—C10 | −39.9 (4) | C17—C18—C19—C20 | 0.5 (6) |
O1—S1—C5—C10 | 82.6 (4) | C18—C19—C20—C15 | 1.3 (6) |
N1—S1—C5—C10 | −165.7 (4) | C16—C15—C20—C19 | −1.7 (6) |
K2—S1—C5—C10 | 130.1 (3) | S2—C15—C20—C19 | 179.4 (3) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O1i | 0.88 (1) | 1.93 (2) | 2.799 (5) | 167 (8) |
O1W—H2W···O4Wi | 0.88 (1) | 2.27 (4) | 3.070 (6) | 151 (6) |
O2W—H3W···O3iii | 0.88 (1) | 2.07 (2) | 2.933 (5) | 167 (6) |
O2W—H4W···N2 | 0.88 (1) | 1.97 (2) | 2.828 (5) | 167 (6) |
O3W—H5W···N1 | 0.87 (1) | 2.02 (2) | 2.872 (5) | 164 (5) |
O3W—H6W···N5i | 0.87 (1) | 1.98 (1) | 2.835 (5) | 166 (4) |
O4W—H7W···O2Wiv | 0.88 (1) | 2.05 (2) | 2.919 (6) | 169 (7) |
O4W—H8W···O4Wv | 0.88 (1) | 2.05 (2) | 2.920 (8) | 168 (9) |
N4—H1N···N4vi | 0.87 (7) | 2.50 (6) | 3.054 (9) | 122 (5) |
N4—H2N···O2vii | 0.93 (7) | 2.57 (7) | 3.431 (7) | 153 (5) |
N8—H3N···O2viii | 0.87 (5) | 2.38 (5) | 3.046 (5) | 134 (4) |
N8—H3N···N3viii | 0.87 (5) | 2.61 (5) | 3.283 (6) | 135 (4) |
Symmetry codes: (i) −x, −y+1, −z+1; (iii) −x, −y+2, −z+1; (iv) x−1, y, z; (v) −x−1, −y+2, −z+1; (vi) −x−1, −y, −z; (vii) x, y−1, z; (viii) x, y, z+1. |
4-[(Pyrimidin-2-yl)sulfamoyl]anilinium
tetraaqua[7-oxo-8-(phenylhydrazinylidene)naphthalene-1,3-disulfonato]sodium(I)
sesquihydrate (IV)
top
Crystal data top
(C10H11N4O2S)[Na(C16H10N2O7S2)(H2O)4]·1.5H2O | F(000) = 1620 |
Mr = 779.74 | Dx = 1.599 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 12.7688 (1) Å | Cell parameters from 35404 reflections |
b = 16.9040 (1) Å | θ = 3.6–70.3° |
c = 15.7411 (1) Å | µ = 2.95 mm−1 |
β = 107.609 (1)° | T = 100 K |
V = 3238.42 (4) Å3 | Block, red |
Z = 4 | 0.12 × 0.08 × 0.04 mm |
Data collection top
XtaLAB AFC11 (RCD3) diffractometer | 5686 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.027 |
ω scans | θmax = 68.3°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017) | h = −15→15 |
Tmin = 0.615, Tmax = 1.000 | k = −20→20 |
59125 measured reflections | l = −18→17 |
5913 independent reflections | |
Refinement top
Refinement on F2 | 13 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0364P)2 + 2.347P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
5913 reflections | Δρmax = 0.26 e Å−3 |
537 parameters | Δρmin = −0.39 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Na1 | −0.36434 (5) | 0.35305 (4) | 0.00412 (4) | 0.02103 (14) | |
S1 | 0.25698 (3) | 0.53159 (2) | 0.56811 (2) | 0.01894 (9) | |
S2 | 0.28977 (3) | 0.35439 (2) | 0.12953 (2) | 0.01723 (9) | |
S3 | 0.34948 (3) | 0.66079 (2) | 0.22267 (2) | 0.01823 (9) | |
O1 | 0.30756 (9) | 0.60882 (7) | 0.58033 (7) | 0.0231 (2) | |
O2 | 0.25734 (9) | 0.48924 (7) | 0.64777 (7) | 0.0232 (2) | |
O1W | −0.35372 (9) | 0.22020 (7) | 0.04238 (8) | 0.0218 (2) | |
O3 | −0.16759 (8) | 0.36126 (6) | 0.04200 (7) | 0.0209 (2) | |
O2W | −0.39276 (13) | 0.36471 (9) | 0.15242 (9) | 0.0366 (3) | |
O4 | 0.23184 (9) | 0.28982 (6) | 0.15504 (8) | 0.0242 (2) | |
O3W | −0.56243 (11) | 0.33362 (8) | −0.06717 (10) | 0.0324 (3) | |
O5 | 0.29466 (9) | 0.35183 (7) | 0.03839 (7) | 0.0247 (3) | |
O4W | −0.40375 (13) | 0.48626 (9) | −0.02427 (12) | 0.0467 (4) | |
H7W | −0.3673 (17) | 0.5308 (9) | −0.0208 (17) | 0.056* | |
H8W | −0.449 (3) | 0.501 (2) | 0.006 (3) | 0.056* | 0.5 |
H14W | −0.463 (2) | 0.499 (2) | −0.068 (2) | 0.056* | 0.5 |
O5W | −0.6489 (2) | 0.33037 (15) | −0.24880 (18) | 0.0323 (5) | 0.5 |
H9W | −0.677 (3) | 0.2873 (16) | −0.279 (2) | 0.039* | 0.5 |
H10W | −0.590 (2) | 0.336 (2) | −0.267 (3) | 0.039* | 0.5 |
O6W | −0.3558 (3) | 0.52405 (18) | 0.16139 (18) | 0.0459 (8) | 0.5 |
H11W | −0.366 (2) | 0.5317 (15) | 0.2141 (10) | 0.055* | |
H12W | −0.367 (4) | 0.4725 (8) | 0.160 (3) | 0.055* | 0.5 |
O7W | −0.4311 (2) | 0.54771 (18) | 0.19266 (18) | 0.0392 (7) | 0.5 |
H13W | −0.451 (3) | 0.566 (3) | 0.2374 (18) | 0.047* | 0.5 |
O6 | 0.40067 (8) | 0.36455 (6) | 0.19268 (7) | 0.0200 (2) | |
O7 | 0.36235 (9) | 0.69334 (7) | 0.14107 (7) | 0.0228 (2) | |
O8 | 0.44918 (9) | 0.62573 (7) | 0.28078 (8) | 0.0297 (3) | |
O9 | 0.29864 (9) | 0.71689 (7) | 0.26880 (7) | 0.0241 (2) | |
N1 | 0.13018 (10) | 0.53245 (8) | 0.50886 (8) | 0.0193 (3) | |
N2 | 0.14382 (11) | 0.63967 (8) | 0.41387 (9) | 0.0205 (3) | |
N3 | −0.02496 (10) | 0.58329 (8) | 0.41174 (9) | 0.0202 (3) | |
N4 | 0.47872 (12) | 0.31848 (9) | 0.37342 (10) | 0.0228 (3) | |
N5 | 0.04786 (10) | 0.34343 (7) | 0.02685 (8) | 0.0165 (3) | |
N6 | −0.02618 (10) | 0.29254 (7) | −0.01560 (8) | 0.0173 (3) | |
C1 | 0.08718 (12) | 0.58593 (9) | 0.44525 (10) | 0.0185 (3) | |
C2 | 0.08701 (13) | 0.69124 (10) | 0.35332 (10) | 0.0216 (3) | |
H2 | 0.1270 | 0.7293 | 0.3313 | 0.026* | |
C3 | −0.02726 (13) | 0.69278 (10) | 0.32031 (11) | 0.0232 (3) | |
H3 | −0.0650 | 0.7314 | 0.2784 | 0.028* | |
C4 | −0.08209 (13) | 0.63587 (10) | 0.35134 (11) | 0.0238 (3) | |
H4 | −0.1600 | 0.6334 | 0.3304 | 0.029* | |
C5 | 0.32606 (12) | 0.47095 (9) | 0.51081 (10) | 0.0197 (3) | |
C6 | 0.35300 (12) | 0.49962 (10) | 0.43696 (10) | 0.0223 (3) | |
H6 | 0.3365 | 0.5527 | 0.4176 | 0.027* | |
C7 | 0.40425 (12) | 0.44943 (10) | 0.39231 (10) | 0.0219 (3) | |
H7 | 0.4236 | 0.4677 | 0.3420 | 0.026* | |
C8 | 0.42703 (12) | 0.37216 (10) | 0.42193 (10) | 0.0205 (3) | |
C9 | 0.40333 (13) | 0.34437 (10) | 0.49661 (11) | 0.0221 (3) | |
H9 | 0.4223 | 0.2919 | 0.5171 | 0.027* | |
C10 | 0.35154 (12) | 0.39416 (10) | 0.54122 (10) | 0.0218 (3) | |
H10 | 0.3336 | 0.3759 | 0.5922 | 0.026* | |
C11 | 0.01948 (12) | 0.40012 (9) | 0.07444 (10) | 0.0159 (3) | |
C12 | −0.09441 (12) | 0.41261 (9) | 0.07379 (9) | 0.0175 (3) | |
C13 | −0.12211 (12) | 0.48735 (9) | 0.10541 (10) | 0.0198 (3) | |
H13 | −0.1955 | 0.4971 | 0.1051 | 0.024* | |
C14 | −0.04523 (12) | 0.54336 (9) | 0.13538 (10) | 0.0188 (3) | |
H14 | −0.0671 | 0.5934 | 0.1516 | 0.023* | |
C15 | 0.06970 (12) | 0.53059 (9) | 0.14404 (10) | 0.0166 (3) | |
C16 | 0.10495 (12) | 0.45694 (9) | 0.11881 (9) | 0.0157 (3) | |
C17 | 0.22061 (12) | 0.44559 (9) | 0.13890 (10) | 0.0168 (3) | |
C18 | 0.29200 (12) | 0.50782 (9) | 0.17202 (10) | 0.0186 (3) | |
H18 | 0.3687 | 0.4999 | 0.1835 | 0.022* | |
C19 | 0.25427 (12) | 0.58168 (9) | 0.18898 (10) | 0.0178 (3) | |
C20 | 0.14397 (12) | 0.59221 (9) | 0.17777 (10) | 0.0178 (3) | |
H20 | 0.1182 | 0.6413 | 0.1929 | 0.021* | |
C21 | −0.00296 (12) | 0.23542 (9) | −0.07255 (10) | 0.0178 (3) | |
C22 | −0.09205 (13) | 0.19251 (9) | −0.12561 (10) | 0.0204 (3) | |
H22 | −0.1643 | 0.2031 | −0.1234 | 0.024* | |
C23 | −0.07414 (14) | 0.13423 (10) | −0.18169 (11) | 0.0237 (3) | |
H23 | −0.1343 | 0.1047 | −0.2182 | 0.028* | |
C24 | 0.03150 (14) | 0.11899 (10) | −0.18464 (11) | 0.0243 (3) | |
H24 | 0.0438 | 0.0786 | −0.2225 | 0.029* | |
C25 | 0.11952 (14) | 0.16297 (10) | −0.13190 (11) | 0.0242 (3) | |
H25 | 0.1916 | 0.1526 | −0.1346 | 0.029* | |
C26 | 0.10358 (13) | 0.22174 (10) | −0.07551 (10) | 0.0211 (3) | |
H26 | 0.1637 | 0.2519 | −0.0398 | 0.025* | |
H1W | −0.349 (2) | 0.2133 (14) | 0.0986 (18) | 0.049 (7)* | |
H2W | −0.299 (2) | 0.1888 (15) | 0.0354 (16) | 0.052 (7)* | |
H3W | −0.360 (2) | 0.3264 (17) | 0.1861 (18) | 0.057 (8)* | |
H4W | −0.461 (3) | 0.3655 (19) | 0.161 (2) | 0.089 (11)* | |
H5W | −0.607 (2) | 0.3395 (16) | −0.0361 (19) | 0.061 (8)* | |
H6W | −0.591 (3) | 0.365 (2) | −0.109 (2) | 0.086 (11)* | |
H1N | −0.0943 (19) | 0.2989 (13) | −0.0086 (14) | 0.039 (6)* | |
H2N | 0.4668 (19) | 0.2671 (15) | 0.3875 (16) | 0.046 (6)* | |
H3N | 0.4510 (18) | 0.3275 (13) | 0.3137 (16) | 0.036 (6)* | |
H4N | 0.552 (2) | 0.3289 (13) | 0.3887 (14) | 0.036 (6)* | |
H5N | −0.0568 (18) | 0.5484 (13) | 0.4332 (14) | 0.034 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Na1 | 0.0167 (3) | 0.0247 (3) | 0.0222 (3) | 0.0009 (2) | 0.0066 (2) | 0.0023 (2) |
S1 | 0.01371 (18) | 0.0258 (2) | 0.01688 (18) | 0.00205 (14) | 0.00401 (14) | 0.00107 (14) |
S2 | 0.01208 (17) | 0.02132 (19) | 0.01829 (19) | 0.00029 (13) | 0.00458 (14) | 0.00044 (14) |
S3 | 0.01672 (18) | 0.02092 (19) | 0.01605 (18) | −0.00479 (14) | 0.00343 (14) | −0.00034 (14) |
O1 | 0.0168 (5) | 0.0278 (6) | 0.0235 (6) | −0.0008 (4) | 0.0044 (4) | −0.0022 (5) |
O2 | 0.0188 (5) | 0.0335 (6) | 0.0174 (5) | 0.0043 (5) | 0.0054 (4) | 0.0033 (5) |
O1W | 0.0204 (6) | 0.0252 (6) | 0.0199 (6) | 0.0006 (5) | 0.0061 (4) | 0.0006 (5) |
O3 | 0.0146 (5) | 0.0233 (6) | 0.0249 (6) | −0.0033 (4) | 0.0061 (4) | −0.0030 (4) |
O2W | 0.0409 (8) | 0.0400 (8) | 0.0350 (7) | 0.0161 (6) | 0.0208 (6) | 0.0089 (6) |
O4 | 0.0180 (5) | 0.0200 (5) | 0.0352 (6) | −0.0002 (4) | 0.0090 (5) | 0.0039 (5) |
O3W | 0.0246 (6) | 0.0369 (7) | 0.0407 (8) | 0.0063 (5) | 0.0171 (6) | 0.0062 (6) |
O5 | 0.0170 (5) | 0.0378 (7) | 0.0201 (6) | 0.0016 (5) | 0.0069 (4) | −0.0037 (5) |
O4W | 0.0522 (9) | 0.0349 (7) | 0.0683 (11) | 0.0142 (7) | 0.0413 (8) | 0.0217 (7) |
O5W | 0.0279 (13) | 0.0334 (14) | 0.0360 (14) | −0.0018 (10) | 0.0103 (11) | −0.0034 (11) |
O6W | 0.070 (2) | 0.0441 (16) | 0.0218 (13) | 0.0273 (15) | 0.0117 (13) | 0.0043 (12) |
O7W | 0.0281 (14) | 0.0483 (17) | 0.0362 (15) | 0.0008 (12) | 0.0021 (11) | 0.0159 (13) |
O6 | 0.0129 (5) | 0.0250 (6) | 0.0204 (5) | 0.0012 (4) | 0.0026 (4) | 0.0015 (4) |
O7 | 0.0257 (6) | 0.0247 (6) | 0.0198 (6) | −0.0074 (5) | 0.0098 (5) | −0.0014 (4) |
O8 | 0.0205 (6) | 0.0305 (6) | 0.0299 (6) | −0.0045 (5) | −0.0047 (5) | 0.0029 (5) |
O9 | 0.0250 (6) | 0.0269 (6) | 0.0223 (6) | −0.0072 (5) | 0.0101 (5) | −0.0067 (5) |
N1 | 0.0130 (6) | 0.0250 (7) | 0.0192 (6) | 0.0018 (5) | 0.0039 (5) | 0.0018 (5) |
N2 | 0.0174 (6) | 0.0246 (7) | 0.0192 (6) | 0.0006 (5) | 0.0050 (5) | 0.0011 (5) |
N3 | 0.0142 (6) | 0.0266 (7) | 0.0201 (7) | 0.0013 (5) | 0.0058 (5) | 0.0025 (5) |
N4 | 0.0166 (7) | 0.0317 (8) | 0.0209 (7) | 0.0058 (6) | 0.0066 (6) | 0.0019 (6) |
N5 | 0.0158 (6) | 0.0176 (6) | 0.0149 (6) | −0.0007 (5) | 0.0028 (5) | 0.0023 (5) |
N6 | 0.0139 (6) | 0.0202 (6) | 0.0172 (6) | −0.0010 (5) | 0.0038 (5) | −0.0005 (5) |
C1 | 0.0158 (7) | 0.0226 (8) | 0.0173 (7) | 0.0023 (6) | 0.0053 (6) | −0.0031 (6) |
C2 | 0.0233 (8) | 0.0234 (8) | 0.0191 (8) | 0.0006 (6) | 0.0078 (6) | −0.0010 (6) |
C3 | 0.0225 (8) | 0.0274 (8) | 0.0193 (8) | 0.0058 (7) | 0.0057 (6) | 0.0030 (6) |
C4 | 0.0168 (8) | 0.0331 (9) | 0.0202 (8) | 0.0056 (6) | 0.0040 (6) | 0.0021 (7) |
C5 | 0.0114 (7) | 0.0282 (8) | 0.0183 (7) | 0.0010 (6) | 0.0028 (6) | 0.0003 (6) |
C6 | 0.0180 (7) | 0.0275 (8) | 0.0202 (8) | 0.0030 (6) | 0.0042 (6) | 0.0036 (6) |
C7 | 0.0163 (7) | 0.0316 (9) | 0.0177 (7) | 0.0027 (6) | 0.0050 (6) | 0.0039 (6) |
C8 | 0.0115 (7) | 0.0304 (9) | 0.0186 (8) | 0.0032 (6) | 0.0032 (6) | 0.0002 (6) |
C9 | 0.0174 (7) | 0.0271 (8) | 0.0214 (8) | 0.0041 (6) | 0.0052 (6) | 0.0039 (6) |
C10 | 0.0159 (7) | 0.0304 (9) | 0.0190 (8) | 0.0014 (6) | 0.0050 (6) | 0.0035 (6) |
C11 | 0.0144 (7) | 0.0181 (7) | 0.0145 (7) | 0.0001 (6) | 0.0036 (5) | 0.0024 (6) |
C12 | 0.0155 (7) | 0.0224 (8) | 0.0140 (7) | −0.0009 (6) | 0.0035 (6) | 0.0024 (6) |
C13 | 0.0150 (7) | 0.0251 (8) | 0.0203 (8) | 0.0015 (6) | 0.0069 (6) | 0.0004 (6) |
C14 | 0.0189 (7) | 0.0205 (8) | 0.0179 (7) | 0.0021 (6) | 0.0067 (6) | 0.0009 (6) |
C15 | 0.0165 (7) | 0.0205 (7) | 0.0125 (7) | −0.0002 (6) | 0.0041 (6) | 0.0030 (6) |
C16 | 0.0153 (7) | 0.0202 (7) | 0.0117 (7) | −0.0006 (6) | 0.0045 (6) | 0.0033 (6) |
C17 | 0.0157 (7) | 0.0207 (7) | 0.0141 (7) | −0.0002 (6) | 0.0048 (6) | 0.0026 (6) |
C18 | 0.0148 (7) | 0.0240 (8) | 0.0161 (7) | −0.0016 (6) | 0.0034 (6) | 0.0037 (6) |
C19 | 0.0175 (7) | 0.0212 (7) | 0.0131 (7) | −0.0032 (6) | 0.0024 (6) | 0.0029 (6) |
C20 | 0.0199 (7) | 0.0189 (7) | 0.0147 (7) | −0.0010 (6) | 0.0051 (6) | 0.0014 (6) |
C21 | 0.0201 (7) | 0.0175 (7) | 0.0155 (7) | 0.0010 (6) | 0.0049 (6) | 0.0021 (6) |
C22 | 0.0189 (7) | 0.0225 (8) | 0.0196 (8) | −0.0017 (6) | 0.0055 (6) | 0.0016 (6) |
C23 | 0.0256 (8) | 0.0234 (8) | 0.0209 (8) | −0.0058 (6) | 0.0051 (7) | −0.0024 (6) |
C24 | 0.0312 (9) | 0.0229 (8) | 0.0187 (8) | 0.0022 (7) | 0.0077 (7) | −0.0019 (6) |
C25 | 0.0208 (8) | 0.0294 (9) | 0.0225 (8) | 0.0046 (7) | 0.0065 (6) | −0.0006 (7) |
C26 | 0.0179 (7) | 0.0247 (8) | 0.0193 (8) | 0.0003 (6) | 0.0034 (6) | −0.0009 (6) |
Geometric parameters (Å, º) top
Na1—O1W | 2.3184 (13) | N5—C11 | 1.3322 (19) |
Na1—O4W | 2.3211 (15) | N6—C21 | 1.409 (2) |
Na1—O3 | 2.4042 (12) | N6—H1N | 0.92 (2) |
Na1—O7i | 2.4237 (12) | C2—C3 | 1.393 (2) |
Na1—O3W | 2.4592 (14) | C2—H2 | 0.9500 |
Na1—O2W | 2.4764 (14) | C3—C4 | 1.364 (2) |
S1—O2 | 1.4428 (11) | C3—H3 | 0.9500 |
S1—O1 | 1.4433 (12) | C4—H4 | 0.9500 |
S1—N1 | 1.6055 (13) | C5—C10 | 1.388 (2) |
S1—C5 | 1.7674 (16) | C5—C6 | 1.395 (2) |
S2—O4 | 1.4419 (11) | C6—C7 | 1.386 (2) |
S2—O5 | 1.4554 (12) | C6—H6 | 0.9500 |
S2—O6 | 1.4735 (11) | C7—C8 | 1.388 (2) |
S2—C17 | 1.8048 (15) | C7—H7 | 0.9500 |
S3—O8 | 1.4506 (12) | C8—C9 | 1.382 (2) |
S3—O7 | 1.4516 (11) | C9—C10 | 1.385 (2) |
S3—O9 | 1.4605 (12) | C9—H9 | 0.9500 |
S3—C19 | 1.7769 (15) | C10—H10 | 0.9500 |
O1W—H1W | 0.88 (3) | C11—C16 | 1.463 (2) |
O1W—H2W | 0.91 (3) | C11—C12 | 1.467 (2) |
O3—C12 | 1.2626 (18) | C12—C13 | 1.441 (2) |
O2W—H3W | 0.86 (3) | C13—C14 | 1.343 (2) |
O2W—H4W | 0.92 (4) | C13—H13 | 0.9500 |
O3W—H5W | 0.86 (3) | C14—C15 | 1.448 (2) |
O3W—H6W | 0.83 (4) | C14—H14 | 0.9500 |
O4W—H7W | 0.879 (10) | C15—C20 | 1.401 (2) |
O4W—H8W | 0.883 (10) | C15—C16 | 1.421 (2) |
O4W—H14W | 0.886 (10) | C16—C17 | 1.427 (2) |
O5W—H9W | 0.883 (10) | C17—C18 | 1.386 (2) |
O5W—H10W | 0.885 (10) | C18—C19 | 1.393 (2) |
O6W—H11W | 0.886 (10) | C18—H18 | 0.9500 |
O6W—H12W | 0.881 (10) | C19—C20 | 1.377 (2) |
O7W—H13W | 0.875 (10) | C20—H20 | 0.9500 |
O7—Na1i | 2.4237 (12) | C21—C22 | 1.394 (2) |
N1—C1 | 1.337 (2) | C21—C26 | 1.395 (2) |
N2—C2 | 1.333 (2) | C22—C23 | 1.387 (2) |
N2—C1 | 1.345 (2) | C22—H22 | 0.9500 |
N3—C4 | 1.344 (2) | C23—C24 | 1.388 (2) |
N3—C1 | 1.369 (2) | C23—H23 | 0.9500 |
N3—H5N | 0.84 (2) | C24—C25 | 1.393 (2) |
N4—C8 | 1.465 (2) | C24—H24 | 0.9500 |
N4—H2N | 0.92 (3) | C25—C26 | 1.388 (2) |
N4—H3N | 0.91 (2) | C25—H25 | 0.9500 |
N4—H4N | 0.91 (2) | C26—H26 | 0.9500 |
N5—N6 | 1.3031 (18) | | |
| | | |
O1W—Na1—O4W | 169.11 (5) | C4—C3—C2 | 116.51 (15) |
O1W—Na1—O3 | 90.96 (4) | C4—C3—H3 | 121.7 |
O4W—Na1—O3 | 98.12 (5) | C2—C3—H3 | 121.7 |
O1W—Na1—O7i | 85.13 (4) | N3—C4—C3 | 119.48 (15) |
O4W—Na1—O7i | 101.30 (5) | N3—C4—H4 | 120.3 |
O3—Na1—O7i | 86.81 (4) | C3—C4—H4 | 120.3 |
O1W—Na1—O3W | 87.73 (5) | C10—C5—C6 | 121.41 (15) |
O4W—Na1—O3W | 84.75 (6) | C10—C5—S1 | 117.89 (12) |
O3—Na1—O3W | 166.97 (5) | C6—C5—S1 | 120.71 (12) |
O7i—Na1—O3W | 80.17 (5) | C7—C6—C5 | 118.90 (15) |
O1W—Na1—O2W | 81.14 (5) | C7—C6—H6 | 120.6 |
O4W—Na1—O2W | 91.10 (6) | C5—C6—H6 | 120.6 |
O3—Na1—O2W | 101.64 (5) | C6—C7—C8 | 119.27 (15) |
O7i—Na1—O2W | 163.94 (5) | C6—C7—H7 | 120.4 |
O3W—Na1—O2W | 90.97 (5) | C8—C7—H7 | 120.4 |
O2—S1—O1 | 116.71 (7) | C9—C8—C7 | 121.88 (15) |
O2—S1—N1 | 104.29 (7) | C9—C8—N4 | 118.81 (15) |
O1—S1—N1 | 113.65 (7) | C7—C8—N4 | 119.30 (14) |
O2—S1—C5 | 106.55 (7) | C8—C9—C10 | 119.06 (15) |
O1—S1—C5 | 108.68 (7) | C8—C9—H9 | 120.5 |
N1—S1—C5 | 106.26 (7) | C10—C9—H9 | 120.5 |
O4—S2—O5 | 115.51 (7) | C9—C10—C5 | 119.43 (15) |
O4—S2—O6 | 111.69 (7) | C9—C10—H10 | 120.3 |
O5—S2—O6 | 110.45 (6) | C5—C10—H10 | 120.3 |
O4—S2—C17 | 108.60 (7) | N5—C11—C16 | 116.76 (13) |
O5—S2—C17 | 105.90 (7) | N5—C11—C12 | 122.51 (13) |
O6—S2—C17 | 103.85 (7) | C16—C11—C12 | 120.25 (13) |
O8—S3—O7 | 113.59 (7) | O3—C12—C13 | 120.68 (13) |
O8—S3—O9 | 112.90 (7) | O3—C12—C11 | 121.14 (14) |
O7—S3—O9 | 112.34 (7) | C13—C12—C11 | 118.06 (13) |
O8—S3—C19 | 105.75 (7) | C14—C13—C12 | 120.66 (14) |
O7—S3—C19 | 105.76 (7) | C14—C13—H13 | 119.7 |
O9—S3—C19 | 105.67 (7) | C12—C13—H13 | 119.7 |
Na1—O1W—H1W | 111.8 (16) | C13—C14—C15 | 122.71 (14) |
Na1—O1W—H2W | 121.3 (16) | C13—C14—H14 | 118.6 |
H1W—O1W—H2W | 103 (2) | C15—C14—H14 | 118.6 |
C12—O3—Na1 | 136.93 (10) | C20—C15—C16 | 121.48 (13) |
Na1—O2W—H3W | 110.0 (18) | C20—C15—C14 | 118.39 (14) |
Na1—O2W—H4W | 124 (2) | C16—C15—C14 | 120.13 (13) |
H3W—O2W—H4W | 102 (3) | C15—C16—C17 | 116.75 (13) |
Na1—O3W—H5W | 119.2 (19) | C15—C16—C11 | 117.08 (13) |
Na1—O3W—H6W | 115 (2) | C17—C16—C11 | 126.18 (13) |
H5W—O3W—H6W | 100 (3) | C18—C17—C16 | 120.02 (14) |
Na1—O4W—H7W | 137.7 (16) | C18—C17—S2 | 113.36 (11) |
Na1—O4W—H8W | 108 (3) | C16—C17—S2 | 126.58 (11) |
H7W—O4W—H8W | 98 (2) | C17—C18—C19 | 121.74 (14) |
Na1—O4W—H14W | 118 (3) | C17—C18—H18 | 119.1 |
H7W—O4W—H14W | 99 (2) | C19—C18—H18 | 119.1 |
H9W—O5W—H10W | 99 (2) | C20—C19—C18 | 119.40 (14) |
H11W—O6W—H12W | 96 (2) | C20—C19—S3 | 121.46 (12) |
S3—O7—Na1i | 138.42 (7) | C18—C19—S3 | 119.13 (11) |
C1—N1—S1 | 123.67 (11) | C19—C20—C15 | 120.10 (14) |
C2—N2—C1 | 117.89 (13) | C19—C20—H20 | 119.9 |
C4—N3—C1 | 122.12 (14) | C15—C20—H20 | 119.9 |
C4—N3—H5N | 121.4 (15) | C22—C21—C26 | 121.42 (14) |
C1—N3—H5N | 116.4 (15) | C22—C21—N6 | 116.56 (13) |
C8—N4—H2N | 109.0 (15) | C26—C21—N6 | 122.01 (14) |
C8—N4—H3N | 109.8 (14) | C23—C22—C21 | 119.28 (15) |
H2N—N4—H3N | 111 (2) | C23—C22—H22 | 120.4 |
C8—N4—H4N | 109.3 (14) | C21—C22—H22 | 120.4 |
H2N—N4—H4N | 111 (2) | C22—C23—C24 | 120.15 (15) |
H3N—N4—H4N | 106.8 (19) | C22—C23—H23 | 119.9 |
N6—N5—C11 | 118.99 (13) | C24—C23—H23 | 119.9 |
N5—N6—C21 | 121.27 (13) | C23—C24—C25 | 119.87 (15) |
N5—N6—H1N | 115.4 (14) | C23—C24—H24 | 120.1 |
C21—N6—H1N | 123.2 (14) | C25—C24—H24 | 120.1 |
N1—C1—N2 | 125.95 (14) | C26—C25—C24 | 121.02 (15) |
N1—C1—N3 | 114.28 (14) | C26—C25—H25 | 119.5 |
N2—C1—N3 | 119.77 (14) | C24—C25—H25 | 119.5 |
N2—C2—C3 | 124.12 (15) | C25—C26—C21 | 118.25 (14) |
N2—C2—H2 | 117.9 | C25—C26—H26 | 120.9 |
C3—C2—H2 | 117.9 | C21—C26—H26 | 120.9 |
| | | |
O8—S3—O7—Na1i | 81.07 (11) | C13—C14—C15—C20 | −178.66 (14) |
O9—S3—O7—Na1i | −149.26 (9) | C13—C14—C15—C16 | 1.2 (2) |
C19—S3—O7—Na1i | −34.46 (12) | C20—C15—C16—C17 | 6.9 (2) |
O2—S1—N1—C1 | 156.92 (13) | C14—C15—C16—C17 | −172.92 (13) |
O1—S1—N1—C1 | 28.75 (15) | C20—C15—C16—C11 | −172.79 (13) |
C5—S1—N1—C1 | −90.72 (14) | C14—C15—C16—C11 | 7.4 (2) |
C11—N5—N6—C21 | 174.83 (13) | N5—C11—C16—C15 | 159.68 (13) |
S1—N1—C1—N2 | 8.8 (2) | C12—C11—C16—C15 | −12.5 (2) |
S1—N1—C1—N3 | −170.92 (11) | N5—C11—C16—C17 | −20.0 (2) |
C2—N2—C1—N1 | −176.66 (15) | C12—C11—C16—C17 | 167.76 (14) |
C2—N2—C1—N3 | 3.0 (2) | C15—C16—C17—C18 | −7.1 (2) |
C4—N3—C1—N1 | 175.88 (14) | C11—C16—C17—C18 | 172.62 (14) |
C4—N3—C1—N2 | −3.8 (2) | C15—C16—C17—S2 | 170.58 (11) |
C1—N2—C2—C3 | −0.2 (2) | C11—C16—C17—S2 | −9.7 (2) |
N2—C2—C3—C4 | −1.9 (2) | O4—S2—C17—C18 | 141.14 (11) |
C1—N3—C4—C3 | 1.6 (2) | O5—S2—C17—C18 | −94.23 (12) |
C2—C3—C4—N3 | 1.1 (2) | O6—S2—C17—C18 | 22.15 (13) |
O2—S1—C5—C10 | 9.38 (14) | O4—S2—C17—C16 | −36.66 (15) |
O1—S1—C5—C10 | 135.92 (12) | O5—S2—C17—C16 | 87.97 (14) |
N1—S1—C5—C10 | −101.41 (13) | O6—S2—C17—C16 | −155.65 (13) |
O2—S1—C5—C6 | −171.14 (12) | C16—C17—C18—C19 | 1.8 (2) |
O1—S1—C5—C6 | −44.60 (14) | S2—C17—C18—C19 | −176.12 (11) |
N1—S1—C5—C6 | 78.07 (14) | C17—C18—C19—C20 | 4.0 (2) |
C10—C5—C6—C7 | 1.3 (2) | C17—C18—C19—S3 | −174.87 (11) |
S1—C5—C6—C7 | −178.11 (12) | O8—S3—C19—C20 | 143.56 (13) |
C5—C6—C7—C8 | 0.2 (2) | O7—S3—C19—C20 | −95.67 (13) |
C6—C7—C8—C9 | −2.2 (2) | O9—S3—C19—C20 | 23.63 (14) |
C6—C7—C8—N4 | 178.48 (14) | O8—S3—C19—C18 | −37.62 (14) |
C7—C8—C9—C10 | 2.5 (2) | O7—S3—C19—C18 | 83.15 (13) |
N4—C8—C9—C10 | −178.13 (14) | O9—S3—C19—C18 | −157.55 (12) |
C8—C9—C10—C5 | −0.9 (2) | C18—C19—C20—C15 | −4.2 (2) |
C6—C5—C10—C9 | −1.0 (2) | S3—C19—C20—C15 | 174.65 (11) |
S1—C5—C10—C9 | 178.47 (12) | C16—C15—C20—C19 | −1.4 (2) |
N6—N5—C11—C16 | −178.41 (12) | C14—C15—C20—C19 | 178.45 (13) |
N6—N5—C11—C12 | −6.4 (2) | N5—N6—C21—C22 | −169.89 (13) |
Na1—O3—C12—C13 | 6.3 (2) | N5—N6—C21—C26 | 10.6 (2) |
Na1—O3—C12—C11 | −169.80 (10) | C26—C21—C22—C23 | 0.9 (2) |
N5—C11—C12—O3 | 13.8 (2) | N6—C21—C22—C23 | −178.63 (14) |
C16—C11—C12—O3 | −174.40 (13) | C21—C22—C23—C24 | 0.1 (2) |
N5—C11—C12—C13 | −162.36 (14) | C22—C23—C24—C25 | −0.7 (2) |
C16—C11—C12—C13 | 9.4 (2) | C23—C24—C25—C26 | 0.5 (3) |
O3—C12—C13—C14 | −176.90 (14) | C24—C25—C26—C21 | 0.4 (2) |
C11—C12—C13—C14 | −0.7 (2) | C22—C21—C26—C25 | −1.1 (2) |
C12—C13—C14—C15 | −4.7 (2) | N6—C21—C26—C25 | 178.40 (14) |
Symmetry code: (i) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O9ii | 0.88 (3) | 1.99 (3) | 2.8404 (16) | 163 (2) |
O1W—H2W···O1ii | 0.91 (3) | 2.24 (3) | 2.8830 (17) | 127 (2) |
O1W—H2W···N2ii | 0.91 (3) | 2.07 (3) | 2.8972 (18) | 150 (2) |
O2W—H3W···O9ii | 0.86 (3) | 2.05 (3) | 2.8852 (18) | 163 (2) |
O2W—H4W···O6iii | 0.92 (4) | 1.98 (4) | 2.8932 (18) | 174 (3) |
O3W—H5W···O5iii | 0.86 (3) | 1.98 (3) | 2.8320 (18) | 178 (3) |
O3W—H6W···O5W | 0.83 (4) | 2.18 (3) | 2.736 (3) | 124 (3) |
O3W—H6W···O6Wiv | 0.83 (4) | 2.09 (4) | 2.853 (3) | 153 (3) |
O3W—H6W···O7Wiv | 0.83 (4) | 2.06 (4) | 2.799 (3) | 148 (3) |
O4W—H7W···O5i | 0.88 (1) | 2.24 (1) | 3.1093 (19) | 169 (2) |
O4W—H8W···O4Wiv | 0.88 (1) | 2.00 (2) | 2.825 (3) | 154 (4) |
O4W—H8W···O6W | 0.88 (1) | 2.41 (5) | 2.871 (3) | 113 (4) |
O4W—H14W···O7Wiv | 0.89 (1) | 2.16 (3) | 2.902 (3) | 140 (4) |
O5W—H9W···O4v | 0.88 (1) | 1.85 (1) | 2.710 (3) | 166 (4) |
O5W—H10W···O8i | 0.89 (1) | 1.99 (1) | 2.843 (3) | 163 (3) |
O6W—H11W···O2vi | 0.89 (1) | 2.22 (2) | 2.893 (3) | 132 (2) |
O6W—H12W···O2W | 0.88 (1) | 1.85 (1) | 2.731 (3) | 178 (5) |
O7W—H13W···O8iii | 0.88 (1) | 1.91 (2) | 2.699 (3) | 150 (3) |
N6—H1N···O3 | 0.92 (2) | 1.75 (2) | 2.5342 (16) | 142 (2) |
N4—H2N···O3Wvii | 0.92 (3) | 1.93 (3) | 2.839 (2) | 171 (2) |
N4—H3N···O6 | 0.91 (2) | 1.92 (2) | 2.8245 (18) | 170 (2) |
N4—H4N···O1viii | 0.91 (2) | 2.01 (2) | 2.8784 (18) | 159.6 (19) |
N4—H4N···O1Wvii | 0.91 (2) | 2.50 (2) | 2.9386 (19) | 110.5 (16) |
N3—H5N···O2vi | 0.84 (2) | 2.57 (2) | 3.0827 (17) | 120.3 (18) |
N3—H5N···N1vi | 0.84 (2) | 2.02 (2) | 2.8655 (19) | 177 (2) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y−1/2, −z+1/2; (iii) x−1, y, z; (iv) −x−1, −y+1, −z; (v) x−1, −y+1/2, z−1/2; (vi) −x, −y+1, −z+1; (vii) x+1, −y+1/2, z+1/2; (viii) −x+1, −y+1, −z+1. |
2-Aminopyridinium 4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline (V)
top
Crystal data top
C5H7N2+·C10H9N4O2S− | F(000) = 720 |
Mr = 344.40 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5796 (2) Å | Cell parameters from 8493 reflections |
b = 19.0371 (5) Å | θ = 3.0–29.5° |
c = 11.2512 (4) Å | µ = 0.23 mm−1 |
β = 121.116 (3)° | T = 123 K |
V = 1573.27 (9) Å3 | Sheet, colourless |
Z = 4 | 0.4 × 0.3 × 0.02 mm |
Data collection top
Oxford Diffraction Xcalibur E diffractometer | 3225 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.040 |
ω scans | θmax = 29.0°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | h = −11→11 |
Tmin = 0.527, Tmax = 1.000 | k = −25→25 |
22193 measured reflections | l = −14→15 |
4082 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0493P)2 + 0.8192P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
4082 reflections | Δρmax = 0.39 e Å−3 |
237 parameters | Δρmin = −0.48 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.87444 (6) | 0.84851 (2) | 0.27777 (4) | 0.02297 (12) | |
O1 | 0.97267 (17) | 0.79251 (7) | 0.25677 (14) | 0.0309 (3) | |
O2 | 0.96376 (16) | 0.87572 (7) | 0.41782 (12) | 0.0271 (3) | |
N1 | 0.83358 (19) | 0.90544 (7) | 0.16260 (15) | 0.0233 (3) | |
N2 | 0.73473 (18) | 1.01144 (7) | 0.05571 (14) | 0.0216 (3) | |
N3 | 0.71259 (19) | 0.98683 (8) | 0.25488 (15) | 0.0239 (3) | |
N4 | 0.1507 (2) | 0.73439 (9) | 0.12033 (18) | 0.0284 (3) | |
N5 | 1.20543 (19) | 1.03376 (7) | 0.15032 (15) | 0.0231 (3) | |
N6 | 1.0916 (3) | 1.14087 (10) | 0.0502 (2) | 0.0411 (4) | |
C1 | 0.7592 (2) | 0.96881 (9) | 0.16105 (17) | 0.0209 (3) | |
C2 | 0.6662 (2) | 1.07527 (9) | 0.04854 (17) | 0.0238 (4) | |
H2 | 0.6475 | 1.1057 | −0.0247 | 0.029* | |
C3 | 0.6214 (2) | 1.09897 (9) | 0.14288 (18) | 0.0258 (4) | |
H3 | 0.5754 | 1.1449 | 0.1382 | 0.031* | |
C4 | 0.6476 (2) | 1.05165 (9) | 0.24444 (18) | 0.0258 (4) | |
H4 | 0.6175 | 1.0661 | 0.3110 | 0.031* | |
C5 | 0.6654 (2) | 0.81161 (8) | 0.23937 (17) | 0.0215 (3) | |
C6 | 0.5823 (2) | 0.76230 (9) | 0.13303 (18) | 0.0266 (4) | |
H6 | 0.6422 | 0.7470 | 0.0864 | 0.032* | |
C7 | 0.4129 (3) | 0.73551 (9) | 0.09498 (18) | 0.0275 (4) | |
H7 | 0.3577 | 0.7015 | 0.0230 | 0.033* | |
C8 | 0.3216 (2) | 0.75825 (8) | 0.16202 (17) | 0.0219 (3) | |
C9 | 0.4076 (2) | 0.80709 (9) | 0.26908 (17) | 0.0235 (3) | |
H9 | 0.3488 | 0.8224 | 0.3164 | 0.028* | |
C10 | 0.5776 (2) | 0.83359 (9) | 0.30745 (17) | 0.0235 (3) | |
H10 | 0.6342 | 0.8669 | 0.3806 | 0.028* | |
C11 | 1.1346 (2) | 1.09647 (9) | 0.15389 (18) | 0.0251 (4) | |
C12 | 1.1082 (2) | 1.10992 (10) | 0.2655 (2) | 0.0316 (4) | |
H12 | 1.0611 | 1.1540 | 0.2721 | 0.038* | |
C13 | 1.1499 (3) | 1.06005 (11) | 0.3633 (2) | 0.0340 (4) | |
H13 | 1.1283 | 1.0688 | 0.4367 | 0.041* | |
C14 | 1.2247 (3) | 0.99557 (11) | 0.3572 (2) | 0.0368 (5) | |
H14 | 1.2565 | 0.9607 | 0.4264 | 0.044* | |
C15 | 1.2502 (3) | 0.98455 (10) | 0.2496 (2) | 0.0313 (4) | |
H15 | 1.3008 | 0.9412 | 0.2437 | 0.038* | |
H1N | 0.109 (3) | 0.6980 (12) | 0.067 (2) | 0.036 (6)* | |
H2N | 0.100 (3) | 0.7493 (12) | 0.165 (2) | 0.038 (6)* | |
H3N | 1.220 (3) | 1.0215 (12) | 0.078 (2) | 0.044 (6)* | |
H4N | 1.045 (3) | 1.1818 (14) | 0.050 (3) | 0.051 (7)* | |
H5N | 1.105 (4) | 1.1256 (13) | −0.021 (3) | 0.060 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0214 (2) | 0.0248 (2) | 0.0239 (2) | 0.00462 (16) | 0.01254 (17) | 0.00161 (16) |
O1 | 0.0288 (7) | 0.0315 (7) | 0.0364 (7) | 0.0096 (5) | 0.0197 (6) | 0.0023 (6) |
O2 | 0.0236 (6) | 0.0309 (7) | 0.0230 (6) | 0.0037 (5) | 0.0092 (5) | 0.0021 (5) |
N1 | 0.0221 (7) | 0.0251 (7) | 0.0242 (7) | 0.0019 (6) | 0.0130 (6) | 0.0013 (6) |
N2 | 0.0188 (7) | 0.0236 (7) | 0.0215 (7) | −0.0033 (5) | 0.0097 (6) | −0.0017 (5) |
N3 | 0.0220 (7) | 0.0278 (7) | 0.0224 (7) | 0.0011 (6) | 0.0119 (6) | 0.0000 (6) |
N4 | 0.0302 (8) | 0.0267 (8) | 0.0333 (9) | −0.0041 (7) | 0.0201 (7) | −0.0066 (7) |
N5 | 0.0230 (7) | 0.0257 (7) | 0.0230 (7) | 0.0009 (6) | 0.0135 (6) | −0.0012 (6) |
N6 | 0.0551 (12) | 0.0302 (9) | 0.0434 (11) | 0.0162 (8) | 0.0292 (10) | 0.0084 (8) |
C1 | 0.0161 (7) | 0.0247 (8) | 0.0203 (8) | −0.0027 (6) | 0.0082 (6) | −0.0017 (6) |
C2 | 0.0219 (8) | 0.0241 (8) | 0.0222 (8) | −0.0031 (7) | 0.0092 (7) | 0.0001 (7) |
C3 | 0.0235 (8) | 0.0219 (8) | 0.0267 (9) | −0.0007 (7) | 0.0092 (7) | −0.0045 (7) |
C4 | 0.0215 (8) | 0.0300 (9) | 0.0247 (8) | −0.0001 (7) | 0.0111 (7) | −0.0047 (7) |
C5 | 0.0238 (8) | 0.0199 (8) | 0.0227 (8) | 0.0031 (6) | 0.0135 (7) | 0.0024 (6) |
C6 | 0.0310 (9) | 0.0265 (8) | 0.0288 (9) | 0.0033 (7) | 0.0201 (8) | −0.0030 (7) |
C7 | 0.0322 (9) | 0.0250 (8) | 0.0270 (9) | −0.0013 (7) | 0.0166 (8) | −0.0071 (7) |
C8 | 0.0261 (8) | 0.0183 (7) | 0.0232 (8) | 0.0027 (6) | 0.0141 (7) | 0.0044 (6) |
C9 | 0.0304 (9) | 0.0229 (8) | 0.0234 (8) | 0.0022 (7) | 0.0183 (7) | 0.0015 (7) |
C10 | 0.0293 (9) | 0.0228 (8) | 0.0203 (8) | 0.0014 (7) | 0.0142 (7) | −0.0009 (6) |
C11 | 0.0195 (8) | 0.0253 (8) | 0.0286 (9) | 0.0006 (7) | 0.0111 (7) | −0.0029 (7) |
C12 | 0.0248 (9) | 0.0353 (10) | 0.0367 (10) | −0.0030 (8) | 0.0173 (8) | −0.0133 (8) |
C13 | 0.0268 (9) | 0.0514 (12) | 0.0281 (9) | −0.0147 (9) | 0.0173 (8) | −0.0168 (9) |
C14 | 0.0405 (11) | 0.0416 (11) | 0.0289 (10) | −0.0055 (9) | 0.0185 (9) | 0.0039 (8) |
C15 | 0.0368 (10) | 0.0270 (9) | 0.0331 (10) | 0.0041 (8) | 0.0202 (9) | 0.0033 (8) |
Geometric parameters (Å, º) top
S1—O2 | 1.4458 (13) | C3—H3 | 0.9500 |
S1—O1 | 1.4520 (12) | C4—H4 | 0.9500 |
S1—N1 | 1.5834 (15) | C5—C10 | 1.388 (2) |
S1—C5 | 1.7592 (17) | C5—C6 | 1.393 (2) |
N1—C1 | 1.361 (2) | C6—C7 | 1.383 (3) |
N2—C2 | 1.334 (2) | C6—H6 | 0.9500 |
N2—C1 | 1.360 (2) | C7—C8 | 1.407 (2) |
N3—C4 | 1.334 (2) | C7—H7 | 0.9500 |
N3—C1 | 1.352 (2) | C8—C9 | 1.393 (2) |
N4—C8 | 1.366 (2) | C9—C10 | 1.384 (2) |
N4—H1N | 0.86 (2) | C9—H9 | 0.9500 |
N4—H2N | 0.87 (2) | C10—H10 | 0.9500 |
N5—C11 | 1.349 (2) | C11—C12 | 1.410 (3) |
N5—C15 | 1.353 (2) | C12—C13 | 1.354 (3) |
N5—H3N | 0.92 (2) | C12—H12 | 0.9500 |
N6—C11 | 1.329 (3) | C13—C14 | 1.403 (3) |
N6—H4N | 0.87 (3) | C13—H13 | 0.9500 |
N6—H5N | 0.92 (3) | C14—C15 | 1.352 (3) |
C2—C3 | 1.379 (2) | C14—H14 | 0.9500 |
C2—H2 | 0.9500 | C15—H15 | 0.9500 |
C3—C4 | 1.379 (3) | | |
| | | |
O2—S1—O1 | 114.52 (8) | C6—C5—S1 | 118.99 (13) |
O2—S1—N1 | 114.53 (8) | C7—C6—C5 | 120.28 (16) |
O1—S1—N1 | 105.72 (8) | C7—C6—H6 | 119.9 |
O2—S1—C5 | 108.04 (8) | C5—C6—H6 | 119.9 |
O1—S1—C5 | 105.70 (8) | C6—C7—C8 | 120.50 (16) |
N1—S1—C5 | 107.81 (8) | C6—C7—H7 | 119.7 |
C1—N1—S1 | 121.43 (12) | C8—C7—H7 | 119.7 |
C2—N2—C1 | 117.44 (14) | N4—C8—C9 | 120.93 (16) |
C4—N3—C1 | 116.41 (15) | N4—C8—C7 | 120.64 (16) |
C8—N4—H1N | 119.2 (15) | C9—C8—C7 | 118.40 (16) |
C8—N4—H2N | 117.6 (15) | C10—C9—C8 | 121.00 (16) |
H1N—N4—H2N | 121 (2) | C10—C9—H9 | 119.5 |
C11—N5—C15 | 121.88 (16) | C8—C9—H9 | 119.5 |
C11—N5—H3N | 121.5 (14) | C9—C10—C5 | 120.19 (16) |
C15—N5—H3N | 116.5 (14) | C9—C10—H10 | 119.9 |
C11—N6—H4N | 119.3 (16) | C5—C10—H10 | 119.9 |
C11—N6—H5N | 117.6 (16) | N6—C11—N5 | 117.51 (17) |
H4N—N6—H5N | 123 (2) | N6—C11—C12 | 124.49 (18) |
N3—C1—N2 | 123.66 (15) | N5—C11—C12 | 117.99 (17) |
N3—C1—N1 | 122.74 (15) | C13—C12—C11 | 119.97 (17) |
N2—C1—N1 | 113.60 (14) | C13—C12—H12 | 120.0 |
N2—C2—C3 | 122.76 (16) | C11—C12—H12 | 120.0 |
N2—C2—H2 | 118.6 | C12—C13—C14 | 120.61 (17) |
C3—C2—H2 | 118.6 | C12—C13—H13 | 119.7 |
C2—C3—C4 | 115.67 (16) | C14—C13—H13 | 119.7 |
C2—C3—H3 | 122.2 | C15—C14—C13 | 117.98 (18) |
C4—C3—H3 | 122.2 | C15—C14—H14 | 121.0 |
N3—C4—C3 | 123.98 (16) | C13—C14—H14 | 121.0 |
N3—C4—H4 | 118.0 | C14—C15—N5 | 121.55 (18) |
C3—C4—H4 | 118.0 | C14—C15—H15 | 119.2 |
C10—C5—C6 | 119.61 (16) | N5—C15—H15 | 119.2 |
C10—C5—S1 | 121.30 (13) | | |
| | | |
O2—S1—N1—C1 | −46.01 (15) | C10—C5—C6—C7 | 0.2 (3) |
O1—S1—N1—C1 | −173.05 (13) | S1—C5—C6—C7 | −176.15 (14) |
C5—S1—N1—C1 | 74.26 (14) | C5—C6—C7—C8 | 0.7 (3) |
C4—N3—C1—N2 | −3.3 (2) | C6—C7—C8—N4 | 176.89 (16) |
C4—N3—C1—N1 | 177.47 (15) | C6—C7—C8—C9 | −1.3 (3) |
C2—N2—C1—N3 | 2.2 (2) | N4—C8—C9—C10 | −177.19 (16) |
C2—N2—C1—N1 | −178.51 (14) | C7—C8—C9—C10 | 1.0 (2) |
S1—N1—C1—N3 | −1.2 (2) | C8—C9—C10—C5 | −0.1 (3) |
S1—N1—C1—N2 | 179.50 (11) | C6—C5—C10—C9 | −0.5 (3) |
C1—N2—C2—C3 | 0.4 (2) | S1—C5—C10—C9 | 175.75 (13) |
N2—C2—C3—C4 | −1.6 (2) | C15—N5—C11—N6 | −178.70 (18) |
C1—N3—C4—C3 | 2.0 (2) | C15—N5—C11—C12 | 0.1 (3) |
C2—C3—C4—N3 | 0.3 (3) | N6—C11—C12—C13 | 177.36 (19) |
O2—S1—C5—C10 | 24.88 (16) | N5—C11—C12—C13 | −1.4 (3) |
O1—S1—C5—C10 | 147.91 (14) | C11—C12—C13—C14 | 1.9 (3) |
N1—S1—C5—C10 | −99.39 (15) | C12—C13—C14—C15 | −1.2 (3) |
O2—S1—C5—C6 | −158.80 (13) | C13—C14—C15—N5 | 0.0 (3) |
O1—S1—C5—C6 | −35.78 (16) | C11—N5—C15—C14 | 0.6 (3) |
N1—S1—C5—C6 | 76.93 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H1N···O2i | 0.86 (2) | 2.04 (2) | 2.895 (2) | 168 (2) |
N4—H2N···O1ii | 0.87 (2) | 2.03 (2) | 2.887 (2) | 174 (2) |
N5—H3N···N2iii | 0.92 (2) | 1.85 (2) | 2.758 (2) | 174 (2) |
N6—H4N···N4iv | 0.87 (3) | 2.39 (3) | 3.085 (2) | 137 (2) |
N6—H5N···N1iii | 0.92 (3) | 2.00 (3) | 2.918 (2) | 173 (3) |
Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) x−1, y, z; (iii) −x+2, −y+2, −z; (iv) −x+1, −y+2, −z. |
Ethanolaminium 4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline monohydrate (VI)
top
Crystal data top
C2H8NO+·C10H9N4O2S−·H2O | F(000) = 696 |
Mr = 329.38 | Dx = 1.503 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.7755 (4) Å | Cell parameters from 3829 reflections |
b = 9.8979 (4) Å | θ = 3.2–29.5° |
c = 11.5366 (4) Å | µ = 0.25 mm−1 |
β = 93.508 (3)° | T = 123 K |
V = 1456.08 (9) Å3 | Fragment, colourless |
Z = 4 | 0.25 × 0.24 × 0.12 mm |
Data collection top
Oxford Diffraction Xcalibur E diffractometer | 2942 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.023 |
ω scans | θmax = 29.5°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | h = −16→17 |
Tmin = 0.904, Tmax = 1.000 | k = −12→12 |
7213 measured reflections | l = −15→15 |
3571 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0415P)2 + 0.609P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3571 reflections | Δρmax = 0.45 e Å−3 |
231 parameters | Δρmin = −0.47 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.22358 (3) | 0.19320 (4) | 0.61905 (3) | 0.01162 (11) | |
O1 | 0.17136 (8) | 0.31689 (11) | 0.58001 (10) | 0.0164 (2) | |
O2 | 0.20716 (8) | 0.15689 (11) | 0.73914 (9) | 0.0150 (2) | |
O3 | 0.45324 (9) | −0.36122 (12) | 0.56317 (11) | 0.0195 (3) | |
O1W | 0.04450 (10) | 0.06888 (14) | 0.88727 (13) | 0.0264 (3) | |
N1 | 0.34262 (10) | 0.21715 (13) | 0.59377 (11) | 0.0131 (3) | |
N2 | 0.51428 (10) | 0.15350 (13) | 0.58746 (11) | 0.0146 (3) | |
N3 | 0.39549 (10) | 0.00832 (13) | 0.68028 (11) | 0.0150 (3) | |
N4 | 0.06716 (12) | −0.25029 (16) | 0.31048 (14) | 0.0204 (3) | |
N5 | 0.33848 (11) | −0.55735 (15) | 0.42864 (13) | 0.0153 (3) | |
C1 | 0.41755 (11) | 0.12192 (16) | 0.62242 (13) | 0.0125 (3) | |
C2 | 0.59122 (12) | 0.06494 (17) | 0.61312 (14) | 0.0167 (3) | |
H2 | 0.6595 | 0.0845 | 0.5894 | 0.020* | |
C3 | 0.57580 (13) | −0.05364 (17) | 0.67255 (14) | 0.0178 (3) | |
H3 | 0.6312 | −0.1156 | 0.6906 | 0.021* | |
C4 | 0.47525 (12) | −0.07671 (17) | 0.70408 (14) | 0.0169 (3) | |
H4 | 0.4617 | −0.1575 | 0.7450 | 0.020* | |
C5 | 0.17356 (11) | 0.06143 (15) | 0.53090 (13) | 0.0119 (3) | |
C6 | 0.14954 (12) | −0.06369 (16) | 0.57665 (14) | 0.0149 (3) | |
H6 | 0.1589 | −0.0789 | 0.6579 | 0.018* | |
C7 | 0.11201 (12) | −0.16636 (17) | 0.50398 (14) | 0.0163 (3) | |
H7 | 0.0946 | −0.2513 | 0.5359 | 0.020* | |
C8 | 0.09943 (11) | −0.14617 (16) | 0.38370 (14) | 0.0150 (3) | |
C9 | 0.12428 (12) | −0.01923 (16) | 0.33835 (13) | 0.0150 (3) | |
H9 | 0.1163 | −0.0040 | 0.2570 | 0.018* | |
C10 | 0.16023 (11) | 0.08336 (16) | 0.41125 (13) | 0.0141 (3) | |
H10 | 0.1760 | 0.1693 | 0.3800 | 0.017* | |
C11 | 0.34327 (12) | −0.37296 (17) | 0.57033 (15) | 0.0184 (3) | |
H11A | 0.3136 | −0.2833 | 0.5878 | 0.022* | |
H11B | 0.3284 | −0.4349 | 0.6347 | 0.022* | |
C12 | 0.29135 (12) | −0.42582 (16) | 0.45860 (15) | 0.0173 (3) | |
H12A | 0.2153 | −0.4374 | 0.4673 | 0.021* | |
H12B | 0.3005 | −0.3601 | 0.3953 | 0.021* | |
H1N | 0.0376 (17) | −0.223 (2) | 0.243 (2) | 0.033 (6)* | |
H2N | 0.0370 (17) | −0.313 (2) | 0.3425 (19) | 0.029 (6)* | |
H3N | 0.4051 (17) | −0.550 (2) | 0.4209 (17) | 0.023 (5)* | |
H4N | 0.3120 (17) | −0.587 (2) | 0.360 (2) | 0.031 (6)* | |
H5N | 0.3293 (17) | −0.625 (2) | 0.483 (2) | 0.032 (6)* | |
H1H | 0.4656 (19) | −0.297 (3) | 0.518 (2) | 0.043 (7)* | |
H1W | 0.095 (2) | 0.097 (3) | 0.833 (3) | 0.065 (9)* | |
H2W | 0.070 (2) | 0.106 (3) | 0.950 (2) | 0.046 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.01262 (17) | 0.01188 (19) | 0.01020 (19) | 0.00106 (13) | −0.00062 (13) | −0.00008 (14) |
O1 | 0.0180 (5) | 0.0138 (6) | 0.0170 (6) | 0.0038 (4) | −0.0017 (4) | 0.0010 (5) |
O2 | 0.0167 (5) | 0.0185 (6) | 0.0099 (5) | 0.0023 (4) | 0.0007 (4) | 0.0001 (4) |
O3 | 0.0162 (5) | 0.0161 (6) | 0.0254 (7) | −0.0015 (5) | −0.0037 (5) | 0.0028 (5) |
O1W | 0.0229 (6) | 0.0330 (8) | 0.0227 (7) | −0.0010 (5) | −0.0029 (5) | −0.0036 (6) |
N1 | 0.0127 (6) | 0.0129 (6) | 0.0135 (6) | 0.0000 (5) | −0.0011 (5) | 0.0009 (5) |
N2 | 0.0147 (6) | 0.0149 (7) | 0.0139 (6) | −0.0009 (5) | −0.0006 (5) | −0.0016 (5) |
N3 | 0.0179 (6) | 0.0144 (7) | 0.0126 (6) | 0.0016 (5) | 0.0012 (5) | 0.0008 (5) |
N4 | 0.0253 (7) | 0.0185 (8) | 0.0171 (8) | −0.0046 (6) | −0.0014 (6) | −0.0029 (6) |
N5 | 0.0164 (7) | 0.0161 (7) | 0.0131 (7) | −0.0015 (5) | −0.0010 (5) | 0.0014 (6) |
C1 | 0.0149 (7) | 0.0137 (7) | 0.0085 (7) | −0.0005 (6) | −0.0017 (5) | −0.0032 (6) |
C2 | 0.0135 (7) | 0.0206 (8) | 0.0158 (8) | 0.0009 (6) | 0.0002 (6) | −0.0049 (7) |
C3 | 0.0199 (8) | 0.0184 (8) | 0.0148 (8) | 0.0061 (6) | −0.0016 (6) | −0.0017 (6) |
C4 | 0.0222 (8) | 0.0147 (8) | 0.0136 (8) | 0.0026 (6) | −0.0004 (6) | −0.0002 (6) |
C5 | 0.0096 (6) | 0.0138 (7) | 0.0122 (7) | 0.0000 (5) | 0.0000 (5) | −0.0008 (6) |
C6 | 0.0149 (7) | 0.0188 (8) | 0.0109 (7) | 0.0001 (6) | 0.0013 (5) | 0.0010 (6) |
C7 | 0.0172 (7) | 0.0155 (8) | 0.0161 (8) | −0.0031 (6) | 0.0017 (6) | 0.0012 (6) |
C8 | 0.0111 (7) | 0.0170 (8) | 0.0169 (8) | 0.0007 (6) | 0.0007 (6) | −0.0036 (6) |
C9 | 0.0152 (7) | 0.0194 (8) | 0.0104 (7) | 0.0022 (6) | 0.0003 (6) | 0.0003 (6) |
C10 | 0.0135 (7) | 0.0154 (7) | 0.0134 (7) | 0.0008 (6) | 0.0007 (5) | 0.0026 (6) |
C11 | 0.0171 (7) | 0.0202 (8) | 0.0178 (8) | −0.0006 (6) | 0.0000 (6) | −0.0022 (7) |
C12 | 0.0168 (7) | 0.0159 (8) | 0.0187 (8) | −0.0007 (6) | −0.0021 (6) | −0.0002 (7) |
Geometric parameters (Å, º) top
S1—O1 | 1.4525 (11) | C2—C3 | 1.379 (2) |
S1—O2 | 1.4588 (11) | C2—H2 | 0.9500 |
S1—N1 | 1.5838 (13) | C3—C4 | 1.376 (2) |
S1—C5 | 1.7505 (15) | C3—H3 | 0.9500 |
O3—C11 | 1.4172 (19) | C4—H4 | 0.9500 |
O3—H1H | 0.84 (3) | C5—C6 | 1.388 (2) |
O1W—H1W | 0.97 (3) | C5—C10 | 1.397 (2) |
O1W—H2W | 0.86 (3) | C6—C7 | 1.384 (2) |
N1—C1 | 1.3694 (19) | C6—H6 | 0.9500 |
N2—C2 | 1.337 (2) | C7—C8 | 1.401 (2) |
N2—C1 | 1.3596 (19) | C7—H7 | 0.9500 |
N3—C4 | 1.337 (2) | C8—C9 | 1.405 (2) |
N3—C1 | 1.346 (2) | C9—C10 | 1.379 (2) |
N4—C8 | 1.379 (2) | C9—H9 | 0.9500 |
N4—H1N | 0.89 (2) | C10—H10 | 0.9500 |
N4—H2N | 0.83 (2) | C11—C12 | 1.507 (2) |
N5—C12 | 1.484 (2) | C11—H11A | 0.9900 |
N5—H3N | 0.86 (2) | C11—H11B | 0.9900 |
N5—H4N | 0.90 (2) | C12—H12A | 0.9900 |
N5—H5N | 0.93 (2) | C12—H12B | 0.9900 |
| | | |
O1—S1—O2 | 114.34 (7) | C3—C4—H4 | 118.2 |
O1—S1—N1 | 104.16 (7) | C6—C5—C10 | 119.86 (14) |
O2—S1—N1 | 114.03 (7) | C6—C5—S1 | 121.69 (12) |
O1—S1—C5 | 107.67 (7) | C10—C5—S1 | 118.44 (12) |
O2—S1—C5 | 107.43 (7) | C7—C6—C5 | 120.08 (14) |
N1—S1—C5 | 108.97 (7) | C7—C6—H6 | 120.0 |
C11—O3—H1H | 108.9 (16) | C5—C6—H6 | 120.0 |
H1W—O1W—H2W | 101 (2) | C6—C7—C8 | 120.63 (15) |
C1—N1—S1 | 121.16 (11) | C6—C7—H7 | 119.7 |
C2—N2—C1 | 116.93 (14) | C8—C7—H7 | 119.7 |
C4—N3—C1 | 116.59 (13) | N4—C8—C7 | 120.77 (15) |
C8—N4—H1N | 113.6 (15) | N4—C8—C9 | 120.40 (15) |
C8—N4—H2N | 114.6 (15) | C7—C8—C9 | 118.78 (14) |
H1N—N4—H2N | 116 (2) | C10—C9—C8 | 120.39 (14) |
C12—N5—H3N | 111.5 (13) | C10—C9—H9 | 119.8 |
C12—N5—H4N | 111.2 (14) | C8—C9—H9 | 119.8 |
H3N—N5—H4N | 104.9 (19) | C9—C10—C5 | 120.26 (14) |
C12—N5—H5N | 114.0 (13) | C9—C10—H10 | 119.9 |
H3N—N5—H5N | 107.1 (18) | C5—C10—H10 | 119.9 |
H4N—N5—H5N | 107.5 (19) | O3—C11—C12 | 111.39 (13) |
N3—C1—N2 | 124.11 (14) | O3—C11—H11A | 109.4 |
N3—C1—N1 | 122.02 (13) | C12—C11—H11A | 109.4 |
N2—C1—N1 | 113.87 (14) | O3—C11—H11B | 109.4 |
N2—C2—C3 | 122.86 (15) | C12—C11—H11B | 109.3 |
N2—C2—H2 | 118.6 | H11A—C11—H11B | 108.0 |
C3—C2—H2 | 118.6 | N5—C12—C11 | 109.89 (13) |
C4—C3—C2 | 115.90 (15) | N5—C12—H12A | 109.7 |
C4—C3—H3 | 122.1 | C11—C12—H12A | 109.7 |
C2—C3—H3 | 122.1 | N5—C12—H12B | 109.7 |
N3—C4—C3 | 123.61 (15) | C11—C12—H12B | 109.7 |
N3—C4—H4 | 118.2 | H12A—C12—H12B | 108.2 |
| | | |
O1—S1—N1—C1 | 178.29 (12) | N1—S1—C5—C6 | 109.60 (13) |
O2—S1—N1—C1 | 52.98 (14) | O1—S1—C5—C10 | 43.52 (13) |
C5—S1—N1—C1 | −67.02 (14) | O2—S1—C5—C10 | 167.11 (11) |
C4—N3—C1—N2 | 0.3 (2) | N1—S1—C5—C10 | −68.88 (13) |
C4—N3—C1—N1 | −179.55 (14) | C10—C5—C6—C7 | −0.3 (2) |
C2—N2—C1—N3 | −0.1 (2) | S1—C5—C6—C7 | −178.76 (12) |
C2—N2—C1—N1 | 179.74 (13) | C5—C6—C7—C8 | 1.0 (2) |
S1—N1—C1—N3 | −4.7 (2) | C6—C7—C8—N4 | 176.66 (15) |
S1—N1—C1—N2 | 175.48 (10) | C6—C7—C8—C9 | −0.8 (2) |
C1—N2—C2—C3 | −0.2 (2) | N4—C8—C9—C10 | −177.60 (14) |
N2—C2—C3—C4 | 0.3 (2) | C7—C8—C9—C10 | −0.1 (2) |
C1—N3—C4—C3 | −0.1 (2) | C8—C9—C10—C5 | 0.8 (2) |
C2—C3—C4—N3 | −0.1 (2) | C6—C5—C10—C9 | −0.6 (2) |
O1—S1—C5—C6 | −138.00 (12) | S1—C5—C10—C9 | 177.88 (11) |
O2—S1—C5—C6 | −14.40 (14) | O3—C11—C12—N5 | 56.48 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H1N···O1Wi | 0.89 (2) | 2.34 (2) | 3.173 (2) | 156 (2) |
N4—H2N···O1Wii | 0.83 (2) | 2.58 (2) | 3.293 (2) | 144.1 (19) |
N5—H3N···O3iii | 0.86 (2) | 2.01 (2) | 2.7762 (18) | 147.2 (18) |
N5—H4N···O2ii | 0.90 (2) | 1.99 (2) | 2.8488 (18) | 159 (2) |
N5—H4N···N3ii | 0.90 (2) | 2.51 (2) | 3.038 (2) | 118.1 (17) |
N5—H5N···O1iv | 0.93 (2) | 2.44 (2) | 3.1006 (18) | 128.4 (17) |
N5—H5N···N1iv | 0.93 (2) | 2.02 (2) | 2.933 (2) | 167.3 (19) |
O3—H1H···N2v | 0.84 (3) | 1.90 (3) | 2.7399 (19) | 177 (2) |
O1W—H1W···O2 | 0.97 (3) | 1.94 (3) | 2.9039 (17) | 174 (3) |
O1W—H2W···O1vi | 0.86 (3) | 2.07 (3) | 2.8997 (18) | 163 (2) |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y−1/2, z−1/2; (iii) −x+1, −y−1, −z+1; (iv) x, y−1, z; (v) −x+1, −y, −z+1; (vi) x, −y+1/2, z+1/2. |
Coordination modes of the SD anion, showing which atoms form bonds to alkali
metal cations. top | (I) | (II) | (III) | (III) |
| Li | Na | K L1 | K L2 |
Donor atom | | | | |
O1 | yes | yes | yes | yes |
O2 | no | no | no | yes |
N sulfamide | no | yes | yes | yes |
N ring 1 | yes | yes | no | yes |
N ring 2 | no | yes | no | yes |
N amine | no | yes | no | no |