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In 2,4-diamino-6-methyl-1,3,5-triazin-1-ium (acetoguanaminium) hydrogen phthalate, C
4H
8N
5+·C
8H
5O
4−, (I), acetoguanaminium hydrogen maleate, C
4H
8N
5+·C
4H
3O
4−, (II), and acetoguanaminium 3-hydroxypicolinate monohydrate, C
4H
8N
5+·C
6H
4NO
3−·H
2O, (III), the acetoguanaminium cations interact with the carboxylate groups of the corresponding anions
via a pair of nearly parallel N—H
O hydrogen bonds, forming
R22(8) ring motifs. In (II) and (III), N—H
N base-pairing is observed, while there is none in (I). In (II), a series of fused
R32(8),
R22(8) and
R32(8) hydrogen-bonded rings plus fused
R22(8),
R62(12) and
R22(8) ring motifs occur alternately, aggregating into a supramolecular ladder-like arrangement. In (III),
R22(8) motifs occur on either side of a further ring formed by pairs of N—H
O hydrogen bonds, forming an array of three fused hydrogen-bonded rings. In (I) and (II), the anions form a typical intramolecular O—H
O hydrogen bond with graph set
S(7), whereas in (III) an intramolecular hydrogen bond with graph set
S(6) is formed.
Supporting information
CCDC references: 693615; 693863; 715740
Data collection: COLLECT (Nonius, 1998) for (I); APEX2 (Bruker, 2004) for (II), (III). Cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998) for (I); APEX2 (Bruker, 2004) and SAINT (Bruker, 2004) for (II); SAINT (Bruker, 2004) for (III). Data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998) for (I); SAINT (Bruker, 2004) and XPREP (Bruker, 2004) for (II); SAINT (Bruker, 2004) for (III). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).
(I) 2,4-diamino-6-methyl-1,3,5-triazinium hydrogen phthalate
top
Crystal data top
C4H8N5+·C8H5O4− | F(000) = 608 |
Mr = 291.27 | Dx = 1.504 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2918 reflections |
a = 7.0743 (2) Å | θ = 3.0–27.5° |
b = 23.4468 (5) Å | µ = 0.12 mm−1 |
c = 8.1134 (1) Å | T = 120 K |
β = 107.063 (1)° | Prism, colourless |
V = 1286.53 (5) Å3 | 0.54 × 0.30 × 0.25 mm |
Z = 4 | |
Data collection top
Bruker Nonius [Model?] CCD area-detector diffractometer | 2586 reflections with I > 2σ(I) |
Radiation source: Bruker-Nonius FR591 rotating anode | Rint = 0.032 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
Detector resolution: 9.091 pixels mm-1 | h = −9→6 |
φ and ω scans | k = −30→30 |
14262 measured reflections | l = −10→10 |
2918 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.077P)2 + 0.3461P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.001 |
2918 reflections | Δρmax = 0.39 e Å−3 |
196 parameters | Δρmin = −0.54 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.074 (10) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional
coordinates. All su's are estimated from the variances of the (full)
variance-covariance matrix. The cell esds are taken into account in the
estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those
flagged by the user for potential systematic errors.
Weighted R-factors wR and all goodnesses of fit S
are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The
observed criterion of F2 > 2sigma(F2) is used only
for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice
as large as those based on F, and R-factors based on
ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.79585 (16) | 0.49071 (4) | 0.57842 (12) | 0.0237 (3) | |
O2 | 0.68567 (15) | 0.49255 (4) | 0.29478 (12) | 0.0222 (3) | |
O3 | 0.66971 (15) | 0.43253 (4) | 0.05273 (12) | 0.0231 (3) | |
O4 | 0.73004 (15) | 0.34393 (4) | −0.00317 (12) | 0.0208 (3) | |
C8 | 0.85269 (17) | 0.40696 (5) | 0.43681 (16) | 0.0141 (3) | |
C9 | 0.83451 (17) | 0.37005 (5) | 0.29319 (15) | 0.0138 (3) | |
C10 | 0.91376 (19) | 0.31492 (5) | 0.32588 (17) | 0.0165 (3) | |
C11 | 1.00897 (19) | 0.29545 (6) | 0.49086 (18) | 0.0190 (4) | |
C12 | 1.0274 (2) | 0.33165 (6) | 0.63018 (17) | 0.0198 (3) | |
C13 | 0.94945 (19) | 0.38637 (6) | 0.60194 (16) | 0.0174 (3) | |
C14 | 0.77395 (18) | 0.46743 (5) | 0.43656 (16) | 0.0158 (3) | |
C15 | 0.73816 (18) | 0.38222 (5) | 0.10306 (16) | 0.0157 (3) | |
N1 | 0.65924 (15) | 0.59420 (4) | 0.61398 (13) | 0.0144 (3) | |
N2 | 0.51882 (16) | 0.60435 (5) | 0.32053 (13) | 0.0167 (3) | |
N3 | 0.51377 (15) | 0.68106 (4) | 0.49744 (13) | 0.0135 (3) | |
N4 | 0.51196 (17) | 0.75246 (5) | 0.68749 (14) | 0.0177 (3) | |
N5 | 0.65107 (16) | 0.66794 (5) | 0.80597 (13) | 0.0158 (3) | |
C2 | 0.56246 (17) | 0.62720 (5) | 0.47553 (15) | 0.0129 (3) | |
C4 | 0.55869 (18) | 0.69951 (5) | 0.66144 (15) | 0.0140 (3) | |
C6 | 0.69943 (18) | 0.61593 (5) | 0.77510 (16) | 0.0152 (3) | |
C7 | 0.7995 (2) | 0.57744 (6) | 0.92052 (18) | 0.0229 (4) | |
H3 | 0.671 (4) | 0.4596 (11) | 0.166 (3) | 0.064 (7)* | |
H10 | 0.90200 | 0.29040 | 0.23320 | 0.0200* | |
H11 | 1.05980 | 0.25860 | 0.50790 | 0.0230* | |
H12 | 1.09160 | 0.31930 | 0.74150 | 0.0240* | |
H13 | 0.96200 | 0.41020 | 0.69620 | 0.0210* | |
H1 | 0.69410 | 0.55990 | 0.59860 | 0.0170* | |
H2A | 0.45810 | 0.62420 | 0.23160 | 0.0200* | |
H2B | 0.55110 | 0.56960 | 0.30830 | 0.0200* | |
H4A | 0.45480 | 0.77390 | 0.60120 | 0.0210* | |
H4B | 0.53860 | 0.76560 | 0.79080 | 0.0210* | |
H7A | 0.91370 | 0.59620 | 0.99430 | 0.0340* | |
H7B | 0.83950 | 0.54310 | 0.87580 | 0.0340* | |
H7C | 0.70970 | 0.56820 | 0.98520 | 0.0340* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0362 (6) | 0.0161 (5) | 0.0172 (5) | 0.0061 (4) | 0.0054 (4) | −0.0029 (4) |
O2 | 0.0305 (5) | 0.0156 (5) | 0.0168 (5) | 0.0070 (4) | 0.0013 (4) | −0.0004 (4) |
O3 | 0.0343 (6) | 0.0163 (5) | 0.0146 (5) | 0.0058 (4) | 0.0008 (4) | −0.0001 (3) |
O4 | 0.0278 (5) | 0.0170 (5) | 0.0157 (5) | −0.0008 (4) | 0.0035 (4) | −0.0038 (3) |
C8 | 0.0130 (5) | 0.0119 (6) | 0.0169 (6) | −0.0004 (4) | 0.0034 (4) | 0.0000 (4) |
C9 | 0.0123 (5) | 0.0130 (6) | 0.0154 (6) | −0.0012 (4) | 0.0031 (4) | −0.0001 (4) |
C10 | 0.0165 (6) | 0.0142 (6) | 0.0190 (6) | −0.0004 (5) | 0.0057 (5) | −0.0020 (5) |
C11 | 0.0190 (6) | 0.0139 (6) | 0.0239 (7) | 0.0029 (5) | 0.0058 (5) | 0.0020 (5) |
C12 | 0.0204 (6) | 0.0183 (6) | 0.0182 (6) | 0.0022 (5) | 0.0017 (5) | 0.0036 (5) |
C13 | 0.0190 (6) | 0.0171 (6) | 0.0145 (6) | 0.0002 (5) | 0.0023 (5) | −0.0012 (5) |
C14 | 0.0155 (6) | 0.0132 (6) | 0.0182 (6) | −0.0005 (5) | 0.0042 (4) | −0.0012 (4) |
C15 | 0.0155 (6) | 0.0151 (6) | 0.0156 (6) | −0.0014 (5) | 0.0034 (5) | −0.0010 (4) |
N1 | 0.0177 (5) | 0.0111 (5) | 0.0136 (5) | 0.0019 (4) | 0.0036 (4) | 0.0004 (4) |
N2 | 0.0240 (6) | 0.0124 (5) | 0.0123 (5) | 0.0017 (4) | 0.0031 (4) | −0.0017 (4) |
N3 | 0.0168 (5) | 0.0117 (5) | 0.0119 (5) | −0.0004 (4) | 0.0040 (4) | −0.0004 (4) |
N4 | 0.0265 (6) | 0.0125 (5) | 0.0129 (5) | 0.0017 (4) | 0.0040 (4) | −0.0020 (4) |
N5 | 0.0181 (5) | 0.0150 (5) | 0.0135 (5) | 0.0005 (4) | 0.0034 (4) | −0.0002 (4) |
C2 | 0.0134 (5) | 0.0123 (6) | 0.0131 (6) | −0.0017 (4) | 0.0040 (4) | 0.0002 (4) |
C4 | 0.0140 (6) | 0.0141 (6) | 0.0143 (6) | −0.0025 (4) | 0.0050 (4) | −0.0002 (4) |
C6 | 0.0141 (6) | 0.0172 (6) | 0.0134 (6) | −0.0010 (5) | 0.0028 (4) | 0.0005 (4) |
C7 | 0.0275 (7) | 0.0220 (7) | 0.0166 (6) | 0.0066 (6) | 0.0026 (5) | 0.0043 (5) |
Geometric parameters (Å, º) top
O1—C14 | 1.2418 (15) | N4—H4A | 0.8600 |
O2—C14 | 1.2801 (16) | C8—C9 | 1.4267 (17) |
O3—C15 | 1.2949 (15) | C8—C13 | 1.3994 (18) |
O4—C15 | 1.2341 (15) | C8—C14 | 1.5231 (17) |
O2—H3 | 1.28 (2) | C9—C15 | 1.5194 (17) |
O3—H3 | 1.12 (2) | C9—C10 | 1.4030 (17) |
N1—C6 | 1.3532 (16) | C10—C11 | 1.3873 (19) |
N1—C2 | 1.3704 (15) | C11—C12 | 1.389 (2) |
N2—C2 | 1.3176 (16) | C12—C13 | 1.389 (2) |
N3—C4 | 1.3455 (15) | C10—H10 | 0.9300 |
N3—C2 | 1.3345 (15) | C11—H11 | 0.9300 |
N4—C4 | 1.3177 (17) | C12—H12 | 0.9300 |
N5—C4 | 1.3785 (16) | C13—H13 | 0.9300 |
N5—C6 | 1.3104 (17) | C6—C7 | 1.4891 (19) |
N1—H1 | 0.8600 | C7—H7A | 0.9600 |
N2—H2A | 0.8600 | C7—H7B | 0.9600 |
N2—H2B | 0.8600 | C7—H7C | 0.9600 |
N4—H4B | 0.8600 | | |
| | | |
O1···N1 | 2.6587 (14) | C10···C6i | 3.4790 (19) |
O1···C14i | 3.2338 (17) | C10···C4iii | 3.3908 (19) |
O2···N2 | 2.9074 (15) | C11···C2i | 3.4742 (19) |
O3···N2ii | 3.0541 (14) | C11···N3i | 3.3946 (18) |
O3···C7iii | 3.3974 (18) | C12···C2i | 3.3978 (19) |
O4···N4iv | 2.8748 (15) | C13···C2iii | 3.5036 (19) |
O4···N2ii | 2.9223 (14) | C14···C2iii | 3.4773 (18) |
O1···H13 | 2.2800 | C14···C14i | 3.4190 (18) |
O1···H7B | 2.6400 | C14···N1iii | 3.3030 (17) |
O1···H1 | 1.8000 | C14···O1i | 3.2338 (17) |
O2···H1 | 2.9100 | C15···N2ii | 3.3984 (16) |
O2···H2B | 2.0600 | C15···C6iii | 3.5154 (19) |
O3···H7Ciii | 2.6100 | C15···N5iii | 3.2715 (18) |
O3···H2Aii | 2.5900 | C15···C7i | 3.464 (2) |
O3···H2Bii | 2.8900 | C2···H4Bv | 2.9100 |
O4···H4Aiv | 2.1000 | C4···H4Bv | 3.0800 |
O4···H10 | 2.3200 | C7···H13viii | 3.0900 |
O4···H2Aii | 2.0800 | C11···H10ix | 3.0600 |
O4···H7Ai | 2.8700 | C14···H1 | 2.6800 |
N1···C14iii | 3.3030 (17) | C14···H2B | 2.8900 |
N1···O1 | 2.6587 (14) | C15···H2Aii | 2.6700 |
N2···O4ii | 2.9223 (14) | C15···H7Ai | 2.8400 |
N2···C15ii | 3.3984 (16) | H1···O1 | 1.8000 |
N2···O3ii | 3.0541 (14) | H1···O2 | 2.9100 |
N2···O2 | 2.9074 (15) | H1···H7B | 2.2200 |
N3···C11i | 3.3946 (18) | H1···C14 | 2.6800 |
N3···N4v | 2.9555 (15) | H1···H2B | 2.2900 |
N4···N3vi | 2.9555 (15) | H2A···O3ii | 2.5900 |
N4···C10iii | 3.3743 (18) | H2A···O4ii | 2.0800 |
N4···O4vii | 2.8748 (15) | H2A···C15ii | 2.6700 |
N5···C9iii | 3.4087 (17) | H2B···O2 | 2.0600 |
N5···C15iii | 3.2715 (18) | H2B···O3ii | 2.8900 |
N3···H4Bv | 2.1400 | H2B···C14 | 2.8900 |
C2···C11i | 3.4742 (19) | H2B···H1 | 2.2900 |
C2···C8iii | 3.3164 (18) | H4A···O4vii | 2.1000 |
C2···C14iii | 3.4773 (18) | H4B···N3vi | 2.1400 |
C2···C13iii | 3.5036 (19) | H4B···C2vi | 2.9100 |
C2···C12i | 3.3978 (19) | H4B···C4vi | 3.0800 |
C4···C9iii | 3.3367 (18) | H7A···O4i | 2.8700 |
C4···C10iii | 3.3908 (19) | H7A···H13viii | 2.4100 |
C6···C10i | 3.4790 (19) | H7A···C15i | 2.8400 |
C6···C9i | 3.5153 (18) | H7B···H1 | 2.2200 |
C6···C15iii | 3.5154 (19) | H7B···O1 | 2.6400 |
C7···O3iii | 3.3974 (18) | H7C···O3iii | 2.6100 |
C7···C15i | 3.464 (2) | H10···O4 | 2.3200 |
C8···C2iii | 3.3164 (18) | H10···C11x | 3.0600 |
C9···C6i | 3.5153 (18) | H13···C7viii | 3.0900 |
C9···N5iii | 3.4087 (17) | H13···H7Aviii | 2.4100 |
C9···C4iii | 3.3367 (18) | H13···O1 | 2.2800 |
C10···N4iii | 3.3743 (18) | | |
| | | |
C14—O2—H3 | 110.9 (11) | O4—C15—C9 | 119.18 (11) |
C15—O3—H3 | 110.3 (13) | O3—C15—O4 | 120.40 (11) |
C2—N1—C6 | 119.48 (10) | O3—C15—C9 | 120.41 (11) |
C2—N3—C4 | 116.15 (10) | C9—C10—H10 | 119.00 |
C4—N5—C6 | 114.98 (10) | C11—C10—H10 | 119.00 |
C2—N1—H1 | 120.00 | C10—C11—H11 | 120.00 |
C6—N1—H1 | 120.00 | C12—C11—H11 | 120.00 |
C2—N2—H2B | 120.00 | C11—C12—H12 | 120.00 |
C2—N2—H2A | 120.00 | C13—C12—H12 | 120.00 |
H2A—N2—H2B | 120.00 | C8—C13—H13 | 119.00 |
H4A—N4—H4B | 120.00 | C12—C13—H13 | 119.00 |
C4—N4—H4A | 120.00 | N1—C2—N2 | 118.27 (11) |
C4—N4—H4B | 120.00 | N2—C2—N3 | 120.97 (11) |
C13—C8—C14 | 113.48 (11) | N1—C2—N3 | 120.76 (10) |
C9—C8—C13 | 118.31 (11) | N3—C4—N5 | 125.73 (11) |
C9—C8—C14 | 128.19 (11) | N4—C4—N5 | 116.62 (11) |
C8—C9—C15 | 128.42 (11) | N3—C4—N4 | 117.64 (11) |
C8—C9—C10 | 117.99 (11) | N1—C6—C7 | 116.97 (11) |
C10—C9—C15 | 113.60 (10) | N5—C6—C7 | 120.17 (11) |
C9—C10—C11 | 122.65 (12) | N1—C6—N5 | 122.85 (11) |
C10—C11—C12 | 119.16 (13) | C6—C7—H7A | 110.00 |
C11—C12—C13 | 119.50 (12) | C6—C7—H7B | 109.00 |
C8—C13—C12 | 122.39 (12) | C6—C7—H7C | 109.00 |
O1—C14—C8 | 117.51 (11) | H7A—C7—H7B | 109.00 |
O2—C14—C8 | 120.75 (11) | H7A—C7—H7C | 109.00 |
O1—C14—O2 | 121.73 (11) | H7B—C7—H7C | 109.00 |
| | | |
C2—N1—C6—C7 | 178.23 (12) | C13—C8—C14—O1 | −2.72 (18) |
C6—N1—C2—N2 | −177.60 (12) | C13—C8—C14—O2 | 178.47 (12) |
C6—N1—C2—N3 | 2.38 (18) | C9—C8—C14—O1 | 175.50 (13) |
C2—N1—C6—N5 | −0.54 (19) | C9—C8—C13—C12 | −0.07 (19) |
C4—N3—C2—N1 | −2.35 (18) | C14—C8—C13—C12 | 178.34 (13) |
C4—N3—C2—N2 | 177.63 (12) | C9—C8—C14—O2 | −3.3 (2) |
C2—N3—C4—N4 | −179.79 (12) | C8—C9—C10—C11 | −0.4 (2) |
C2—N3—C4—N5 | 0.65 (19) | C10—C9—C15—O4 | 2.68 (18) |
C4—N5—C6—C7 | −179.80 (12) | C8—C9—C15—O3 | 4.4 (2) |
C6—N5—C4—N3 | 1.05 (19) | C8—C9—C15—O4 | −177.29 (13) |
C6—N5—C4—N4 | −178.51 (12) | C15—C9—C10—C11 | 179.65 (13) |
C4—N5—C6—N1 | −1.07 (19) | C10—C9—C15—O3 | −175.67 (12) |
C14—C8—C9—C10 | −177.73 (12) | C9—C10—C11—C12 | 0.0 (2) |
C14—C8—C9—C15 | 2.2 (2) | C10—C11—C12—C13 | 0.4 (2) |
C13—C8—C9—C15 | −179.63 (12) | C11—C12—C13—C8 | −0.3 (2) |
C13—C8—C9—C10 | 0.41 (18) | | |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+3/2, z−1/2; (vi) x, −y+3/2, z+1/2; (vii) −x+1, y+1/2, −z+1/2; (viii) −x+2, −y+1, −z+2; (ix) x, −y+1/2, z+1/2; (x) x, −y+1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.80 | 2.6587 (14) | 173 |
N2—H2A···O3ii | 0.86 | 2.59 | 3.0541 (14) | 115 |
N2—H2A···O4ii | 0.86 | 2.08 | 2.9223 (14) | 167 |
N2—H2B···O2 | 0.86 | 2.06 | 2.9074 (15) | 168 |
O3—H3···O2 | 1.12 (2) | 1.28 (2) | 2.3916 (13) | 175 (2) |
N4—H4A···O4vii | 0.86 | 2.10 | 2.8748 (15) | 149 |
N4—H4B···N3vi | 0.86 | 2.14 | 2.9555 (15) | 158 |
C10—H10···O4 | 0.93 | 2.32 | 2.6913 (16) | 104 |
C13—H13···O1 | 0.93 | 2.28 | 2.6609 (17) | 104 |
Symmetry codes: (ii) −x+1, −y+1, −z; (vi) x, −y+3/2, z+1/2; (vii) −x+1, y+1/2, −z+1/2. |
(II) 2,4-diamino-6-methyl-1,3,5-triazin-1-ium hydrogen maleate
top
Crystal data top
C4H8N5+·C4H3O4− | Z = 2 |
Mr = 241.22 | F(000) = 252 |
Triclinic, P1 | Dx = 1.493 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1921 (3) Å | Cell parameters from 3779 reflections |
b = 8.2359 (3) Å | θ = 2.5–32.4° |
c = 9.4775 (4) Å | µ = 0.12 mm−1 |
α = 98.287 (2)° | T = 293 K |
β = 104.656 (2)° | Plate-like, colorless |
γ = 91.032 (3)° | 0.22 × 0.18 × 0.16 mm |
V = 536.58 (4) Å3 | |
Data collection top
Bruker Kappa APEXII CCD area-detector diffractometer | 3779 independent reflections |
Radiation source: fine-focus sealed tube | 2607 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω and φ scan | θmax = 32.4°, θmin = 2.5° |
Absorption correction: multi-scan (Blessing, 1995) | h = −10→10 |
Tmin = 0.974, Tmax = 0.981 | k = −12→12 |
13516 measured reflections | l = −13→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0865P)2 + 0.1115P] where P = (Fo2 + 2Fc2)/3 |
3779 reflections | (Δ/σ)max = 0.001 |
156 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional
coordinates. All su's are estimated from the variances of the (full)
variance-covariance matrix. The cell esds are taken into account in the
estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not relevant to
the choice of reflections for refinement. R-factors based on
F2 are statistically about twice as large as those based on F,
and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.29101 (16) | 0.47306 (12) | 0.57202 (12) | 0.0358 (3) | |
N2 | 0.23873 (19) | 0.34969 (14) | 0.33003 (12) | 0.0441 (4) | |
N3 | 0.38794 (16) | 0.20652 (13) | 0.51373 (11) | 0.0363 (3) | |
N4 | 0.53588 (19) | 0.07940 (15) | 0.70623 (14) | 0.0457 (4) | |
N5 | 0.43865 (18) | 0.33738 (14) | 0.76624 (12) | 0.0399 (3) | |
C2 | 0.30591 (18) | 0.34067 (15) | 0.47085 (13) | 0.0336 (3) | |
C4 | 0.45226 (19) | 0.21006 (15) | 0.65985 (14) | 0.0353 (3) | |
C6 | 0.35816 (19) | 0.46583 (16) | 0.71766 (14) | 0.0369 (3) | |
C7 | 0.3359 (3) | 0.61225 (19) | 0.82164 (17) | 0.0503 (5) | |
O1 | 0.12718 (18) | 0.75173 (13) | 0.48301 (11) | 0.0526 (4) | |
O2 | 0.07583 (19) | 0.63810 (13) | 0.25017 (12) | 0.0537 (4) | |
O3 | −0.0875 (2) | 0.69956 (14) | 0.00684 (11) | 0.0639 (4) | |
O4 | −0.2559 (2) | 0.89879 (14) | −0.07827 (12) | 0.0575 (4) | |
C8 | 0.0698 (2) | 0.75762 (15) | 0.34939 (14) | 0.0374 (4) | |
C9 | −0.0111 (2) | 0.91341 (15) | 0.30547 (14) | 0.0407 (4) | |
C10 | −0.1043 (2) | 0.94639 (15) | 0.17320 (14) | 0.0406 (4) | |
C11 | −0.1544 (2) | 0.84338 (17) | 0.02636 (14) | 0.0414 (4) | |
H1 | 0.23940 | 0.56000 | 0.54320 | 0.0430* | |
H2A | 0.24760 | 0.26830 | 0.26460 | 0.0530* | |
H2B | 0.18580 | 0.43700 | 0.30320 | 0.0530* | |
H4A | 0.54740 | −0.00380 | 0.64350 | 0.0550* | |
H4B | 0.57890 | 0.07740 | 0.79920 | 0.0550* | |
H7A | 0.39300 | 0.59500 | 0.92110 | 0.0760* | |
H7B | 0.20160 | 0.62980 | 0.80970 | 0.0760* | |
H7C | 0.39880 | 0.70690 | 0.80150 | 0.0760* | |
H3 | −0.02850 | 0.67630 | 0.08680 | 0.0960* | |
H9 | 0.00600 | 1.00110 | 0.38210 | 0.0490* | |
H10 | −0.14500 | 1.05290 | 0.17330 | 0.0490* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0449 (6) | 0.0267 (5) | 0.0335 (5) | 0.0108 (4) | 0.0049 (4) | 0.0052 (4) |
N2 | 0.0647 (8) | 0.0351 (5) | 0.0295 (5) | 0.0189 (5) | 0.0043 (5) | 0.0073 (4) |
N3 | 0.0455 (6) | 0.0304 (5) | 0.0317 (5) | 0.0143 (4) | 0.0054 (4) | 0.0069 (4) |
N4 | 0.0604 (7) | 0.0388 (6) | 0.0365 (6) | 0.0232 (5) | 0.0056 (5) | 0.0116 (4) |
N5 | 0.0497 (6) | 0.0356 (5) | 0.0315 (5) | 0.0139 (5) | 0.0041 (4) | 0.0055 (4) |
C2 | 0.0395 (6) | 0.0286 (5) | 0.0317 (5) | 0.0082 (4) | 0.0061 (5) | 0.0059 (4) |
C4 | 0.0406 (6) | 0.0317 (5) | 0.0333 (6) | 0.0115 (5) | 0.0063 (5) | 0.0083 (4) |
C6 | 0.0425 (6) | 0.0318 (6) | 0.0338 (6) | 0.0075 (5) | 0.0054 (5) | 0.0037 (4) |
C7 | 0.0673 (10) | 0.0378 (7) | 0.0401 (7) | 0.0135 (7) | 0.0076 (7) | −0.0031 (5) |
O1 | 0.0796 (8) | 0.0429 (5) | 0.0323 (5) | 0.0219 (5) | 0.0055 (5) | 0.0100 (4) |
O2 | 0.0847 (8) | 0.0349 (5) | 0.0366 (5) | 0.0279 (5) | 0.0055 (5) | 0.0051 (4) |
O3 | 0.1107 (11) | 0.0448 (6) | 0.0297 (5) | 0.0351 (6) | 0.0051 (6) | 0.0037 (4) |
O4 | 0.0817 (8) | 0.0488 (6) | 0.0367 (5) | 0.0225 (6) | 0.0006 (5) | 0.0136 (4) |
C8 | 0.0466 (7) | 0.0310 (6) | 0.0340 (6) | 0.0097 (5) | 0.0073 (5) | 0.0079 (4) |
C9 | 0.0613 (8) | 0.0281 (5) | 0.0315 (6) | 0.0110 (5) | 0.0090 (6) | 0.0046 (4) |
C10 | 0.0589 (8) | 0.0286 (5) | 0.0355 (6) | 0.0156 (5) | 0.0117 (6) | 0.0082 (4) |
C11 | 0.0572 (8) | 0.0354 (6) | 0.0318 (6) | 0.0126 (6) | 0.0087 (5) | 0.0098 (5) |
Geometric parameters (Å, º) top
O1—C8 | 1.2371 (16) | N2—H2B | 0.8600 |
O2—C8 | 1.2690 (17) | N2—H2A | 0.8600 |
O3—C11 | 1.2927 (19) | N4—H4B | 0.8600 |
O4—C11 | 1.2250 (18) | N4—H4A | 0.8600 |
O3—H3 | 0.8200 | C6—C7 | 1.482 (2) |
N1—C6 | 1.3526 (17) | C7—H7C | 0.9600 |
N1—C2 | 1.3691 (16) | C7—H7A | 0.9600 |
N2—C2 | 1.3129 (16) | C7—H7B | 0.9600 |
N3—C2 | 1.3287 (17) | C8—C9 | 1.4888 (18) |
N3—C4 | 1.3403 (16) | C9—C10 | 1.3319 (18) |
N4—C4 | 1.3186 (18) | C10—C11 | 1.4769 (18) |
N5—C6 | 1.3015 (18) | C9—H9 | 0.9300 |
N5—C4 | 1.3692 (17) | C10—H10 | 0.9300 |
N1—H1 | 0.8600 | | |
| | | |
O1···C2i | 3.3425 (19) | C8···C4vii | 3.467 (2) |
O1···C9ii | 3.4143 (17) | C8···N4vii | 3.308 (2) |
O1···N1 | 2.7423 (15) | C8···O3 | 3.1182 (16) |
O2···C6i | 3.321 (2) | C9···N4vii | 3.447 (2) |
O2···N2 | 2.7852 (16) | C9···O1ii | 3.4143 (17) |
O2···C11 | 3.0752 (18) | C9···C4i | 3.423 (2) |
O2···O3 | 2.4375 (15) | C10···C11iv | 3.556 (2) |
O3···N2iii | 3.0650 (15) | C10···O4iv | 3.246 (2) |
O3···O2 | 2.4375 (15) | C10···C4i | 3.592 (2) |
O3···C8 | 3.1182 (16) | C11···N2iii | 3.4184 (17) |
O4···C10iv | 3.246 (2) | C11···C10iv | 3.556 (2) |
O4···N4v | 2.8346 (17) | C11···C11iv | 3.545 (2) |
O4···N2iii | 2.9406 (16) | C11···O2 | 3.0752 (18) |
O1···H1 | 1.8800 | C8···H3 | 2.4000 |
O1···H9ii | 2.5800 | C8···H2B | 2.7900 |
O2···H7Bi | 2.8400 | C8···H1 | 2.7000 |
O2···H1 | 2.9000 | C9···H9ii | 2.9300 |
O2···H3 | 1.6200 | C9···H3 | 2.6100 |
O2···H2B | 1.9300 | C11···H2Aiii | 2.6900 |
O3···H2Biii | 2.8900 | H1···H7B | 2.5900 |
O3···H2Aiii | 2.5900 | H1···H7C | 2.5400 |
O4···H7Cvi | 2.8100 | H1···H2B | 2.2900 |
O4···H2Aiii | 2.0900 | H1···O1 | 1.8800 |
O4···H4Bv | 2.1900 | H1···O2 | 2.9000 |
O4···H4Av | 2.8900 | H1···C8 | 2.7000 |
N1···O1 | 2.7423 (15) | H2A···O3iii | 2.5900 |
N1···C2vii | 3.3968 (17) | H2A···O4iii | 2.0900 |
N2···O2 | 2.7852 (16) | H2A···C11iii | 2.6900 |
N2···C11iii | 3.4184 (17) | H2B···O2 | 1.9300 |
N2···C6vii | 3.4089 (19) | H2B···O3iii | 2.8900 |
N2···O4iii | 2.9406 (16) | H2B···C8 | 2.7900 |
N2···O3iii | 3.0650 (15) | H2B···H1 | 2.2900 |
N3···N4viii | 3.0660 (17) | H3···O2 | 1.6200 |
N4···O4ix | 2.8346 (17) | H3···C9 | 2.6100 |
N4···C9vii | 3.447 (2) | H3···C8 | 2.4000 |
N4···N3viii | 3.0660 (17) | H4A···N3viii | 2.2100 |
N4···C8vii | 3.308 (2) | H4A···O4ix | 2.8900 |
N3···H4Aviii | 2.2100 | H4B···O4ix | 2.1900 |
N5···H7Ax | 2.8700 | H7A···H7Ax | 2.5800 |
C2···N1vii | 3.3968 (17) | H7A···N5x | 2.8700 |
C2···O1i | 3.3425 (19) | H7B···H1 | 2.5900 |
C4···C8vii | 3.467 (2) | H7B···O2i | 2.8400 |
C4···C10i | 3.592 (2) | H7C···H1 | 2.5400 |
C4···C9i | 3.423 (2) | H7C···O4xi | 2.8100 |
C6···O2i | 3.321 (2) | H9···O1ii | 2.5800 |
C6···C8i | 3.425 (2) | H9···C9ii | 2.9300 |
C6···N2vii | 3.4089 (19) | H9···H9ii | 2.2600 |
C8···C6i | 3.425 (2) | | |
| | | |
C11—O3—H3 | 109.00 | N1—C6—C7 | 116.83 (12) |
C2—N1—C6 | 119.39 (11) | C6—C7—H7B | 109.00 |
C2—N3—C4 | 115.87 (11) | C6—C7—H7C | 109.00 |
C4—N5—C6 | 115.48 (11) | H7A—C7—H7B | 109.00 |
C2—N1—H1 | 120.00 | H7A—C7—H7C | 109.00 |
C6—N1—H1 | 120.00 | H7B—C7—H7C | 109.00 |
C2—N2—H2A | 120.00 | C6—C7—H7A | 109.00 |
C2—N2—H2B | 120.00 | O1—C8—O2 | 123.24 (13) |
H2A—N2—H2B | 120.00 | O2—C8—C9 | 119.39 (12) |
H4A—N4—H4B | 120.00 | O1—C8—C9 | 117.37 (12) |
C4—N4—H4A | 120.00 | C8—C9—C10 | 129.89 (12) |
C4—N4—H4B | 120.00 | C9—C10—C11 | 131.29 (12) |
N2—C2—N3 | 120.60 (11) | O3—C11—C10 | 120.92 (12) |
N1—C2—N2 | 118.47 (11) | O4—C11—C10 | 118.76 (13) |
N1—C2—N3 | 120.94 (11) | O3—C11—O4 | 120.28 (12) |
N3—C4—N5 | 125.89 (12) | C8—C9—H9 | 115.00 |
N4—C4—N5 | 116.65 (12) | C10—C9—H9 | 115.00 |
N3—C4—N4 | 117.46 (12) | C9—C10—H10 | 114.00 |
N5—C6—C7 | 120.74 (12) | C11—C10—H10 | 114.00 |
N1—C6—N5 | 122.43 (12) | | |
| | | |
C6—N1—C2—N2 | 179.56 (13) | C6—N5—C4—N3 | −1.2 (2) |
C6—N1—C2—N3 | −1.05 (19) | C4—N5—C6—N1 | 0.5 (2) |
C2—N1—C6—C7 | −179.33 (14) | C4—N5—C6—C7 | −179.63 (14) |
C2—N1—C6—N5 | 0.6 (2) | O1—C8—C9—C10 | −170.33 (16) |
C4—N3—C2—N2 | 179.79 (13) | O2—C8—C9—C10 | 9.2 (2) |
C2—N3—C4—N4 | −179.47 (13) | C8—C9—C10—C11 | −1.8 (3) |
C4—N3—C2—N1 | 0.41 (19) | C9—C10—C11—O3 | −8.3 (3) |
C2—N3—C4—N5 | 0.7 (2) | C9—C10—C11—O4 | 174.06 (16) |
C6—N5—C4—N4 | 179.02 (13) | | |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z; (iv) −x, −y+2, −z; (v) x−1, y+1, z−1; (vi) x−1, y, z−1; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y, −z+1; (ix) x+1, y−1, z+1; (x) −x+1, −y+1, −z+2; (xi) x+1, y, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.88 | 2.7423 (15) | 179 |
N2—H2A···O3iii | 0.86 | 2.59 | 3.0650 (15) | 116 |
N2—H2A···O4iii | 0.86 | 2.09 | 2.9406 (16) | 169 |
N2—H2B···O2 | 0.86 | 1.93 | 2.7852 (16) | 177 |
O3—H3···O2 | 0.82 | 1.62 | 2.4375 (15) | 176 |
N4—H4A···N3viii | 0.86 | 2.21 | 3.0660 (17) | 173 |
N4—H4B···O4ix | 0.86 | 2.19 | 2.8346 (17) | 132 |
C9—H9···O1ii | 0.93 | 2.58 | 3.4143 (17) | 150 |
Symmetry codes: (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z; (viii) −x+1, −y, −z+1; (ix) x+1, y−1, z+1. |
(III) 2,4-diamino-6-methyl-1,3,5-triazinium 3-hydroxypicolinate monohydrate
top
Crystal data top
C4H8N5+·C6H4NO3−·H2O | F(000) = 592 |
Mr = 282.27 | Dx = 1.442 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3233 reflections |
a = 7.0397 (16) Å | θ = 2.8–28.4° |
b = 24.680 (5) Å | µ = 0.11 mm−1 |
c = 7.5047 (19) Å | T = 296 K |
β = 94.462 (7)° | Chunk, colourless |
V = 1299.9 (5) Å3 | 0.56 × 0.42 × 0.28 mm |
Z = 4 | |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 3233 independent reflections |
Radiation source: fine-focus sealed tube | 2090 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
φ and ω scans | θmax = 28.4°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.939, Tmax = 0.969 | k = −32→19 |
10842 measured reflections | l = −10→9 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0729P)2 + 0.252P] where P = (Fo2 + 2Fc2)/3 |
3233 reflections | (Δ/σ)max < 0.001 |
191 parameters | Δρmax = 0.24 e Å−3 |
3 restraints | Δρmin = −0.19 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional
coordinates. All su's are estimated from the variances of the (full)
variance-covariance matrix. The cell esds are taken into account in the
estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not relevant to
the choice of reflections for refinement. R-factors based on
F2 are statistically about twice as large as those based on F,
and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.4970 (2) | 0.54462 (5) | 0.29495 (19) | 0.0396 (4) | |
N2 | 0.7324 (2) | 0.48069 (6) | 0.3382 (2) | 0.0488 (5) | |
N3 | 0.4543 (2) | 0.45687 (5) | 0.1802 (2) | 0.0412 (5) | |
N4 | 0.1705 (2) | 0.43923 (6) | 0.0267 (2) | 0.0495 (5) | |
N5 | 0.2094 (2) | 0.52480 (6) | 0.1388 (2) | 0.0417 (5) | |
C2 | 0.5628 (2) | 0.49280 (6) | 0.2702 (2) | 0.0381 (5) | |
C4 | 0.2825 (2) | 0.47337 (6) | 0.1182 (2) | 0.0392 (5) | |
C6 | 0.3210 (2) | 0.55867 (7) | 0.2275 (2) | 0.0396 (5) | |
C7 | 0.2589 (3) | 0.61504 (7) | 0.2581 (3) | 0.0514 (6) | |
O1 | 0.9117 (2) | 0.56798 (5) | 0.5168 (2) | 0.0673 (5) | |
O2 | 0.6960 (2) | 0.63282 (6) | 0.4812 (2) | 0.0587 (5) | |
O3 | 0.7440 (2) | 0.72142 (6) | 0.6472 (2) | 0.0698 (6) | |
N6 | 1.1557 (2) | 0.63392 (6) | 0.7091 (2) | 0.0506 (5) | |
C8 | 0.9812 (3) | 0.65177 (6) | 0.6571 (2) | 0.0407 (5) | |
C9 | 0.9204 (3) | 0.70349 (7) | 0.7004 (3) | 0.0492 (6) | |
C10 | 1.0479 (4) | 0.73694 (8) | 0.7986 (3) | 0.0654 (8) | |
C11 | 1.2240 (4) | 0.71853 (9) | 0.8486 (3) | 0.0693 (9) | |
C12 | 1.2752 (3) | 0.66644 (9) | 0.8022 (3) | 0.0608 (7) | |
C13 | 0.8553 (3) | 0.61401 (7) | 0.5446 (3) | 0.0462 (6) | |
O1W | 0.7024 (3) | 0.66313 (6) | 0.1112 (3) | 0.0789 (8) | |
H1 | 0.56820 | 0.56790 | 0.35330 | 0.0470* | |
H2A | 0.77690 | 0.44860 | 0.32530 | 0.0590* | |
H2B | 0.80050 | 0.50470 | 0.39630 | 0.0590* | |
H4A | 0.20900 | 0.40680 | 0.00790 | 0.0590* | |
H4B | 0.05870 | 0.44930 | −0.01460 | 0.0590* | |
H7A | 0.12930 | 0.61950 | 0.21050 | 0.0770* | |
H7B | 0.33910 | 0.63970 | 0.19950 | 0.0770* | |
H7C | 0.26800 | 0.62240 | 0.38400 | 0.0770* | |
H3 | 0.68810 | 0.69840 | 0.58400 | 0.1050* | |
H10 | 1.01200 | 0.77170 | 0.82970 | 0.0780* | |
H11 | 1.31090 | 0.74060 | 0.91390 | 0.0830* | |
H12 | 1.39700 | 0.65400 | 0.83760 | 0.0730* | |
H1W | 0.710 (4) | 0.6949 (7) | 0.095 (4) | 0.097 (10)* | |
H2W | 0.714 (5) | 0.6586 (13) | 0.220 (3) | 0.136 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0392 (8) | 0.0302 (7) | 0.0483 (8) | −0.0028 (6) | −0.0028 (6) | −0.0039 (6) |
N2 | 0.0472 (9) | 0.0336 (7) | 0.0630 (10) | 0.0021 (6) | −0.0121 (8) | −0.0024 (6) |
N3 | 0.0422 (8) | 0.0290 (7) | 0.0515 (9) | −0.0013 (6) | −0.0029 (7) | 0.0003 (6) |
N4 | 0.0430 (9) | 0.0343 (7) | 0.0695 (11) | −0.0032 (6) | −0.0069 (8) | −0.0071 (7) |
N5 | 0.0360 (8) | 0.0342 (7) | 0.0544 (9) | −0.0001 (6) | 0.0002 (7) | −0.0029 (6) |
C2 | 0.0425 (9) | 0.0296 (8) | 0.0417 (9) | −0.0015 (7) | −0.0002 (7) | 0.0035 (6) |
C4 | 0.0397 (9) | 0.0322 (8) | 0.0456 (9) | −0.0037 (7) | 0.0032 (8) | 0.0015 (7) |
C6 | 0.0389 (9) | 0.0337 (8) | 0.0462 (10) | −0.0029 (7) | 0.0038 (8) | 0.0000 (7) |
C7 | 0.0486 (11) | 0.0373 (9) | 0.0680 (13) | 0.0031 (8) | 0.0019 (9) | −0.0076 (8) |
O1 | 0.0675 (10) | 0.0387 (7) | 0.0919 (11) | 0.0034 (7) | −0.0184 (8) | −0.0219 (7) |
O2 | 0.0516 (8) | 0.0495 (8) | 0.0720 (10) | 0.0006 (6) | −0.0136 (7) | −0.0033 (7) |
O3 | 0.0686 (10) | 0.0400 (8) | 0.0990 (13) | 0.0121 (7) | −0.0052 (9) | −0.0107 (7) |
N6 | 0.0543 (10) | 0.0410 (8) | 0.0541 (9) | 0.0004 (7) | −0.0109 (8) | −0.0045 (7) |
C8 | 0.0501 (10) | 0.0308 (8) | 0.0406 (9) | −0.0014 (7) | −0.0010 (8) | 0.0004 (7) |
C9 | 0.0611 (12) | 0.0350 (9) | 0.0513 (11) | 0.0018 (8) | 0.0028 (9) | −0.0011 (8) |
C10 | 0.0912 (18) | 0.0379 (10) | 0.0657 (14) | −0.0029 (11) | −0.0027 (12) | −0.0131 (9) |
C11 | 0.0868 (18) | 0.0515 (12) | 0.0656 (14) | −0.0159 (12) | −0.0187 (13) | −0.0116 (10) |
C12 | 0.0620 (13) | 0.0555 (12) | 0.0618 (13) | −0.0048 (10) | −0.0154 (11) | −0.0058 (10) |
C13 | 0.0496 (11) | 0.0374 (9) | 0.0507 (11) | −0.0031 (8) | −0.0026 (8) | −0.0001 (8) |
O1W | 0.1168 (16) | 0.0356 (8) | 0.0838 (14) | −0.0087 (9) | 0.0039 (11) | −0.0032 (8) |
Geometric parameters (Å, º) top
O1—C13 | 1.227 (2) | N4—H4A | 0.8600 |
O2—C13 | 1.271 (3) | N4—H4B | 0.8600 |
O3—C9 | 1.349 (3) | N6—C12 | 1.322 (3) |
O3—H3 | 0.8200 | N6—C8 | 1.335 (2) |
O1W—H1W | 0.796 (18) | C6—C7 | 1.482 (2) |
O1W—H2W | 0.82 (2) | C7—H7B | 0.9600 |
N1—C2 | 1.378 (2) | C7—H7A | 0.9600 |
N1—C6 | 1.347 (2) | C7—H7C | 0.9600 |
N2—C2 | 1.296 (2) | C8—C13 | 1.500 (3) |
N3—C4 | 1.326 (2) | C8—C9 | 1.393 (2) |
N3—C2 | 1.321 (2) | C9—C10 | 1.388 (3) |
N4—C4 | 1.311 (2) | C10—C11 | 1.346 (4) |
N5—C6 | 1.295 (2) | C11—C12 | 1.387 (3) |
N5—C4 | 1.383 (2) | C10—H10 | 0.9300 |
N1—H1 | 0.8600 | C11—H11 | 0.9300 |
N2—H2A | 0.8600 | C12—H12 | 0.9300 |
N2—H2B | 0.8600 | | |
| | | |
O1···N6 | 2.701 (2) | C10···C9v | 3.533 (3) |
O1···N2i | 2.912 (2) | C13···C4ii | 3.518 (3) |
O1···C4ii | 3.316 (2) | C6···H4Bvii | 3.0100 |
O1···N2 | 2.787 (2) | C8···H2Ai | 3.0000 |
O1W···O3iii | 2.875 (2) | C8···H7Cviii | 3.0700 |
O1W···O2 | 2.880 (3) | C9···H10iii | 2.9700 |
O1W···N4iv | 2.898 (2) | C9···H1Wv | 2.99 (2) |
O2···O1W | 2.880 (3) | C12···H7Bix | 3.0500 |
O2···O3 | 2.526 (2) | C12···H2Ai | 3.0100 |
O2···N1 | 2.890 (2) | C13···H1 | 2.6400 |
O2···C7 | 3.415 (3) | C13···H2W | 2.79 (3) |
O3···O1Wv | 2.875 (2) | C13···H3 | 2.4200 |
O3···O2 | 2.526 (2) | C13···H2B | 2.9300 |
O1···H2Bi | 2.7500 | H1···H7C | 2.5300 |
O1···H2Ai | 2.4400 | H1···O1 | 2.6300 |
O1···H2B | 1.9400 | H1···H2B | 2.2600 |
O1···H1 | 2.6300 | H1···O2 | 2.0400 |
O1W···H4Aiv | 2.0600 | H1···C13 | 2.6400 |
O1W···H7B | 2.7500 | H1W···C9iii | 2.99 (2) |
O1W···H12vi | 2.8600 | H1W···O3iii | 2.112 (18) |
O2···H3 | 1.8000 | H2A···C12i | 3.0100 |
O2···H1 | 2.0400 | H2A···O1i | 2.4400 |
O2···H2W | 2.07 (2) | H2A···N6i | 2.1100 |
O3···H1Wv | 2.112 (18) | H2A···C8i | 3.0000 |
N1···C2ii | 3.449 (2) | H2B···O1i | 2.7500 |
N1···O2 | 2.890 (2) | H2B···O1 | 1.9400 |
N2···O1 | 2.787 (2) | H2B···H1 | 2.2600 |
N2···C6ii | 3.449 (2) | H2B···C13 | 2.9300 |
N2···O1i | 2.912 (2) | H2W···C13 | 2.79 (3) |
N2···N6i | 2.965 (2) | H2W···O2 | 2.07 (2) |
N4···O1Wiv | 2.898 (2) | H2W···H4Aiv | 2.4400 |
N4···N5vii | 2.994 (2) | H3···C13 | 2.4200 |
N5···N4vii | 2.994 (2) | H3···O2 | 1.8000 |
N6···N2i | 2.965 (2) | H4A···H2Wiv | 2.4400 |
N6···O1 | 2.701 (2) | H4A···O1Wiv | 2.0600 |
N3···H12i | 2.9400 | H4B···H7Avii | 2.5500 |
N5···H4Bvii | 2.1400 | H4B···N5vii | 2.1400 |
N6···H7Cviii | 2.6400 | H4B···C6vii | 3.0100 |
N6···H2Ai | 2.1100 | H7A···H4Bvii | 2.5500 |
C2···N1ii | 3.449 (2) | H7B···C12vi | 3.0500 |
C2···C4iv | 3.298 (2) | H7B···O1W | 2.7500 |
C4···O1ii | 3.316 (2) | H7C···H1 | 2.5300 |
C4···C2iv | 3.298 (2) | H7C···C8x | 3.0700 |
C4···C13ii | 3.518 (3) | H7C···N6x | 2.6400 |
C6···N2ii | 3.449 (2) | H10···C9v | 2.9700 |
C7···O2 | 3.415 (3) | H12···O1Wix | 2.8600 |
C9···C10iii | 3.533 (3) | H12···N3i | 2.9400 |
| | | |
C9—O3—H3 | 109.00 | C6—C7—H7B | 109.00 |
H1W—O1W—H2W | 106 (3) | C6—C7—H7C | 109.00 |
C2—N1—C6 | 119.83 (14) | H7A—C7—H7B | 109.00 |
C2—N3—C4 | 116.65 (13) | H7B—C7—H7C | 110.00 |
C4—N5—C6 | 115.70 (14) | H7A—C7—H7C | 109.00 |
C6—N1—H1 | 120.00 | N6—C8—C9 | 121.80 (17) |
C2—N1—H1 | 120.00 | N6—C8—C13 | 116.72 (15) |
C2—N2—H2A | 120.00 | C9—C8—C13 | 121.46 (18) |
C2—N2—H2B | 120.00 | O3—C9—C8 | 121.61 (18) |
H2A—N2—H2B | 120.00 | C8—C9—C10 | 118.1 (2) |
H4A—N4—H4B | 120.00 | O3—C9—C10 | 120.28 (18) |
C4—N4—H4B | 120.00 | C9—C10—C11 | 119.4 (2) |
C4—N4—H4A | 120.00 | C10—C11—C12 | 119.7 (2) |
C8—N6—C12 | 119.17 (16) | N6—C12—C11 | 121.9 (2) |
N1—C2—N3 | 120.32 (13) | O2—C13—C8 | 116.69 (16) |
N2—C2—N3 | 121.64 (14) | O1—C13—O2 | 124.21 (19) |
N1—C2—N2 | 118.03 (14) | O1—C13—C8 | 119.09 (18) |
N3—C4—N4 | 118.78 (14) | C11—C10—H10 | 120.00 |
N3—C4—N5 | 125.45 (14) | C9—C10—H10 | 120.00 |
N4—C4—N5 | 115.76 (14) | C10—C11—H11 | 120.00 |
N5—C6—C7 | 120.74 (15) | C12—C11—H11 | 120.00 |
N1—C6—C7 | 117.22 (15) | N6—C12—H12 | 119.00 |
N1—C6—N5 | 122.04 (15) | C11—C12—H12 | 119.00 |
C6—C7—H7A | 109.00 | | |
| | | |
C6—N1—C2—N2 | −179.51 (15) | C8—N6—C12—C11 | 0.5 (3) |
C6—N1—C2—N3 | 0.2 (2) | N6—C8—C9—O3 | 179.85 (17) |
C2—N1—C6—N5 | 0.0 (2) | N6—C8—C9—C10 | 0.8 (3) |
C2—N1—C6—C7 | −179.78 (15) | C13—C8—C9—O3 | 1.8 (3) |
C4—N3—C2—N1 | −0.5 (2) | C13—C8—C9—C10 | −177.28 (19) |
C4—N3—C2—N2 | 179.24 (15) | N6—C8—C13—O1 | 5.2 (3) |
C2—N3—C4—N4 | 179.40 (15) | N6—C8—C13—O2 | −173.62 (17) |
C2—N3—C4—N5 | 0.6 (2) | C9—C8—C13—O1 | −176.69 (19) |
C6—N5—C4—N3 | −0.4 (2) | C9—C8—C13—O2 | 4.5 (3) |
C6—N5—C4—N4 | −179.25 (14) | O3—C9—C10—C11 | −179.2 (2) |
C4—N5—C6—N1 | 0.1 (2) | C8—C9—C10—C11 | −0.1 (3) |
C4—N5—C6—C7 | 179.86 (15) | C9—C10—C11—C12 | −0.3 (3) |
C12—N6—C8—C9 | −0.9 (3) | C10—C11—C12—N6 | 0.2 (3) |
C12—N6—C8—C13 | 177.21 (18) | | |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z; (v) x, −y+3/2, z+1/2; (vi) x−1, y, z−1; (vii) −x, −y+1, −z; (viii) x+1, y, z; (ix) x+1, y, z+1; (x) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.86 | 2.04 | 2.890 (2) | 169 |
O1W—H1W···O3iii | 0.796 (18) | 2.112 (18) | 2.875 (2) | 161 (3) |
N2—H2A···O1i | 0.86 | 2.44 | 2.912 (2) | 115 |
N2—H2A···N6i | 0.86 | 2.11 | 2.965 (2) | 172 |
N2—H2B···O1 | 0.86 | 1.94 | 2.787 (2) | 169 |
O1W—H2W···O2 | 0.82 (2) | 2.07 (2) | 2.880 (3) | 166 (3) |
O3—H3···O2 | 0.82 | 1.80 | 2.526 (2) | 147 |
N4—H4A···O1Wiv | 0.86 | 2.06 | 2.898 (2) | 164 |
N4—H4B···N5vii | 0.86 | 2.14 | 2.994 (2) | 175 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (iii) x, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z; (vii) −x, −y+1, −z. |
Selected geometric parameters for (I), (II) and (III) (Å, °) top | (I) | (II) | (III) |
N1—C2 | 1.3704 (15) | 1.3691 (16) | 1.378 (2) |
N1—C6 | 1.3532 (16) | 1.3526 (17) | 1.347 (2) |
N3—C4 | 1.3455 (15) | 1.3403 (16) | 1.326 (2) |
N3—C2 | 1.3345 (15) | 1.3287 (17) | 1.321 (2) |
N5—C4 | 1.3785 (16) | 1.3692 (17) | 1.383 (2) |
N5—C6 | 1.3104 (17) | 1.3015 (18) | 1.295 (2) |
| | | |
C2—N1—C6 | 119.48 (10) | 119.39 (11) | 119.83 (14) |
C2—N3—C4 | 116.15 (10) | 115.87 (11) | 116.65 (13) |
C4—N5—C6 | 114.98 (10) | 115.48 (11) | 115.70 (14) |
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