Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622006684/dg3030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622006684/dg3030Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622006684/dg3030IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622006684/dg3030IIIsup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622006684/dg3030Isup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622006684/dg3030IIsup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622006684/dg3030IIIsup7.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229622006684/dg3030sup8.pdf |
CCDC references: 2182644; 2182643; 2182642
For all structures, data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020), Mercury (Macrae et al., 2020) and POVRay (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2020) and publCIF (Westrip, 2010).
C4H8N3O+·Br− | F(000) = 384 |
Mr = 194.04 | Dx = 1.786 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7252 (4) Å | Cell parameters from 1473 reflections |
b = 7.7772 (4) Å | θ = 2.8–26.4° |
c = 10.7406 (5) Å | µ = 5.62 mm−1 |
β = 97.969 (1)° | T = 293 K |
V = 721.79 (6) Å3 | Plate, colourless |
Z = 4 | 0.25 × 0.25 × 0.05 mm |
Bruker APEXII CCD diffractometer | 1258 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.029 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 26.4°, θmin = 2.8° |
Tmin = 0.626, Tmax = 0.936 | h = −10→10 |
8609 measured reflections | k = −9→9 |
1473 independent reflections | l = −13→13 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.022 | w = 1/[σ2(Fo2) + (0.0212P)2 + 0.322P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.049 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.24 e Å−3 |
1473 reflections | Δρmin = −0.30 e Å−3 |
88 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0158 (10) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.13199 (2) | 0.72299 (3) | 0.04499 (2) | 0.04228 (11) | |
N3 | 0.48199 (19) | 0.1452 (2) | 0.15946 (17) | 0.0352 (4) | |
N1 | 0.3696 (2) | 0.3966 (3) | 0.1251 (2) | 0.0431 (5) | |
O5 | 0.5736 (2) | 0.5805 (2) | 0.1800 (2) | 0.0783 (7) | |
N2 | 0.2176 (2) | 0.1490 (3) | 0.0829 (2) | 0.0505 (5) | |
H2B | 0.211603 | 0.038614 | 0.081112 | 0.061* | |
H2A | 0.136571 | 0.210092 | 0.059521 | 0.061* | |
C2 | 0.3502 (3) | 0.2241 (3) | 0.1214 (2) | 0.0354 (5) | |
C4 | 0.6017 (2) | 0.2711 (3) | 0.2003 (2) | 0.0411 (5) | |
H4A | 0.689357 | 0.258356 | 0.154495 | 0.049* | |
H4B | 0.637259 | 0.261043 | 0.289679 | 0.049* | |
C3 | 0.5049 (3) | −0.0373 (3) | 0.1823 (3) | 0.0479 (6) | |
H3B | 0.522699 | −0.058188 | 0.271244 | 0.072* | |
H3C | 0.592789 | −0.075710 | 0.145111 | 0.072* | |
H3A | 0.414424 | −0.098978 | 0.145721 | 0.072* | |
C5 | 0.5206 (3) | 0.4386 (3) | 0.1701 (2) | 0.0467 (6) | |
H1 | 0.306 (3) | 0.472 (3) | 0.101 (2) | 0.044 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.03312 (14) | 0.03972 (16) | 0.05203 (17) | 0.00201 (9) | −0.00112 (9) | 0.00022 (10) |
N3 | 0.0294 (9) | 0.0284 (9) | 0.0464 (11) | 0.0023 (7) | 0.0004 (8) | 0.0004 (8) |
N1 | 0.0422 (11) | 0.0305 (11) | 0.0553 (13) | 0.0076 (8) | 0.0015 (9) | 0.0052 (9) |
O5 | 0.0697 (13) | 0.0376 (11) | 0.126 (2) | −0.0135 (9) | 0.0097 (13) | −0.0058 (11) |
N2 | 0.0332 (10) | 0.0411 (11) | 0.0718 (14) | 0.0030 (8) | −0.0117 (10) | −0.0003 (10) |
C2 | 0.0347 (11) | 0.0352 (11) | 0.0355 (11) | 0.0053 (9) | 0.0025 (9) | 0.0009 (9) |
C4 | 0.0291 (11) | 0.0413 (13) | 0.0528 (14) | −0.0017 (9) | 0.0054 (10) | −0.0028 (10) |
C3 | 0.0416 (12) | 0.0322 (13) | 0.0670 (17) | 0.0075 (9) | −0.0021 (11) | 0.0014 (11) |
C5 | 0.0473 (13) | 0.0370 (14) | 0.0568 (16) | −0.0043 (10) | 0.0111 (11) | −0.0019 (11) |
N3—C2 | 1.317 (3) | N2—H2B | 0.8600 |
N3—C3 | 1.450 (3) | N2—H2A | 0.8600 |
N3—C4 | 1.455 (3) | C4—C5 | 1.496 (3) |
N1—C2 | 1.352 (3) | C4—H4A | 0.9700 |
N1—C5 | 1.379 (3) | C4—H4B | 0.9700 |
N1—H1 | 0.83 (2) | C3—H3B | 0.9600 |
O5—C5 | 1.195 (3) | C3—H3C | 0.9600 |
N2—C2 | 1.311 (3) | C3—H3A | 0.9600 |
C2—N3—C3 | 127.06 (19) | C5—C4—H4A | 111.2 |
C2—N3—C4 | 109.85 (18) | N3—C4—H4B | 111.2 |
C3—N3—C4 | 122.12 (17) | C5—C4—H4B | 111.2 |
C2—N1—C5 | 110.81 (19) | H4A—C4—H4B | 109.1 |
C2—N1—H1 | 128.4 (18) | N3—C3—H3B | 109.5 |
C5—N1—H1 | 120.7 (18) | N3—C3—H3C | 109.5 |
C2—N2—H2B | 120.0 | H3B—C3—H3C | 109.5 |
C2—N2—H2A | 120.0 | N3—C3—H3A | 109.5 |
H2B—N2—H2A | 120.0 | H3B—C3—H3A | 109.5 |
N2—C2—N3 | 125.8 (2) | H3C—C3—H3A | 109.5 |
N2—C2—N1 | 123.5 (2) | O5—C5—N1 | 126.1 (2) |
N3—C2—N1 | 110.67 (19) | O5—C5—C4 | 128.2 (2) |
N3—C4—C5 | 102.86 (17) | N1—C5—C4 | 105.64 (19) |
N3—C4—H4A | 111.2 | ||
C3—N3—C2—N2 | −8.5 (4) | C2—N3—C4—C5 | −4.3 (2) |
C4—N3—C2—N2 | −177.3 (2) | C3—N3—C4—C5 | −173.8 (2) |
C3—N3—C2—N1 | 172.5 (2) | C2—N1—C5—O5 | 177.3 (3) |
C4—N3—C2—N1 | 3.7 (3) | C2—N1—C5—C4 | −1.5 (3) |
C5—N1—C2—N2 | 179.6 (2) | N3—C4—C5—O5 | −175.4 (3) |
C5—N1—C2—N3 | −1.3 (3) | N3—C4—C5—N1 | 3.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Br1 | 0.82 | 2.50 | 3.315 (2) | 173.4 (19) |
N2—H2B···Br1i | 0.86 | 2.57 | 3.408 (2) | 167 |
N2—H2A···Br1ii | 0.86 | 2.51 | 3.3197 (19) | 158 |
C3—H3A···Br1i | 0.96 | 2.90 | 3.861 (3) | 177 |
C4—H4A···Br1iii | 0.97 | 2.82 | 3.747 (2) | 160 |
Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z. |
C7H6NO2+·C4H8N3O− | F(000) = 264 |
Mr = 250.26 | Dx = 1.403 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9887 (4) Å | Cell parameters from 3487 reflections |
b = 6.6098 (3) Å | θ = 1.8–30.2° |
c = 11.4753 (6) Å | µ = 0.11 mm−1 |
β = 102.080 (2)° | T = 296 K |
V = 592.52 (5) Å3 | Plate, colourless |
Z = 2 | 0.58 × 0.31 × 0.29 mm |
Bruker APEXII CCD diffractometer | 2802 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.029 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 30.2°, θmin = 1.8° |
Tmin = 0.526, Tmax = 0.745 | h = −11→11 |
12356 measured reflections | k = −9→9 |
3487 independent reflections | l = −16→16 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0741P)2 + 0.0054P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.126 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.21 e Å−3 |
3487 reflections | Δρmin = −0.23 e Å−3 |
168 parameters | Absolute structure: Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: −0.3 (5) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O2 | 1.1891 (2) | 0.7538 (3) | 0.10917 (14) | 0.0422 (4) | |
O1 | 1.2878 (2) | 0.7301 (3) | 0.30461 (14) | 0.0443 (4) | |
O5 | 1.2219 (2) | 0.2816 (3) | 0.50838 (15) | 0.0510 (5) | |
N1 | 1.1233 (3) | 0.3877 (3) | 0.31563 (17) | 0.0364 (4) | |
N2 | 0.9891 (3) | 0.4032 (3) | 0.11484 (17) | 0.0411 (5) | |
H2A | 0.922002 | 0.350684 | 0.053936 | 0.062* | |
H2B | 1.037368 | 0.517785 | 0.108395 | 0.062* | |
N3 | 0.9538 (2) | 0.1330 (3) | 0.24130 (17) | 0.0371 (4) | |
N8 | 1.6643 (3) | 1.3369 (4) | 0.4223 (2) | 0.0498 (6) | |
H8A | 1.719074 | 1.449209 | 0.423439 | 0.075* | |
H8B | 1.673196 | 1.266985 | 0.486449 | 0.075* | |
C6 | 1.3765 (3) | 1.0129 (3) | 0.20618 (19) | 0.0305 (4) | |
C7 | 1.4772 (3) | 1.0823 (4) | 0.31201 (19) | 0.0333 (5) | |
H7 | 1.488580 | 1.004053 | 0.380574 | 0.040* | |
C2 | 1.0178 (3) | 0.3089 (3) | 0.21715 (18) | 0.0319 (5) | |
C10 | 1.4491 (3) | 1.3093 (4) | 0.1069 (2) | 0.0437 (6) | |
H10 | 1.440669 | 1.385072 | 0.037659 | 0.052* | |
C3 | 0.8375 (3) | 0.0046 (4) | 0.1598 (2) | 0.0437 (6) | |
H3A | 0.746392 | −0.038874 | 0.196803 | 0.066* | |
H3B | 0.898264 | −0.111474 | 0.140027 | 0.066* | |
H3C | 0.790681 | 0.078849 | 0.088556 | 0.066* | |
C8 | 1.5621 (3) | 1.2689 (4) | 0.31709 (19) | 0.0347 (5) | |
C5 | 1.1348 (3) | 0.2577 (4) | 0.4100 (2) | 0.0373 (5) | |
C9 | 1.5462 (3) | 1.3803 (4) | 0.2121 (2) | 0.0413 (6) | |
H9 | 1.601932 | 1.504059 | 0.213370 | 0.050* | |
C4 | 1.0170 (3) | 0.0832 (4) | 0.3665 (2) | 0.0394 (5) | |
H4A | 1.078528 | −0.044220 | 0.375370 | 0.047* | |
H4B | 0.924136 | 0.075954 | 0.408945 | 0.047* | |
C11 | 1.3629 (3) | 1.1249 (4) | 0.1027 (2) | 0.0385 (5) | |
H11 | 1.297219 | 1.077792 | 0.031180 | 0.046* | |
C12 | 1.2785 (3) | 0.8179 (3) | 0.20560 (18) | 0.0326 (5) | |
H1 | 1.188 (5) | 0.505 (8) | 0.314 (3) | 0.080 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0490 (9) | 0.0366 (8) | 0.0361 (8) | −0.0059 (8) | −0.0022 (7) | −0.0018 (7) |
O1 | 0.0590 (11) | 0.0374 (9) | 0.0340 (8) | −0.0112 (8) | 0.0038 (7) | 0.0003 (7) |
O5 | 0.0641 (11) | 0.0475 (11) | 0.0357 (9) | 0.0069 (10) | −0.0026 (8) | −0.0004 (8) |
N1 | 0.0396 (11) | 0.0331 (10) | 0.0338 (10) | 0.0006 (8) | 0.0014 (8) | 0.0009 (8) |
N2 | 0.0450 (11) | 0.0404 (11) | 0.0339 (10) | −0.0033 (9) | −0.0008 (8) | 0.0034 (9) |
N3 | 0.0376 (10) | 0.0340 (10) | 0.0379 (9) | −0.0028 (8) | 0.0035 (8) | 0.0009 (8) |
N8 | 0.0569 (13) | 0.0476 (12) | 0.0408 (11) | −0.0137 (11) | 0.0006 (9) | −0.0083 (10) |
C6 | 0.0296 (10) | 0.0292 (10) | 0.0327 (10) | 0.0023 (8) | 0.0063 (8) | −0.0010 (8) |
C7 | 0.0362 (11) | 0.0323 (11) | 0.0315 (10) | 0.0020 (8) | 0.0071 (8) | −0.0006 (9) |
C2 | 0.0300 (10) | 0.0316 (11) | 0.0331 (10) | 0.0036 (8) | 0.0045 (8) | −0.0014 (8) |
C10 | 0.0430 (13) | 0.0451 (14) | 0.0408 (13) | −0.0015 (11) | 0.0039 (10) | 0.0132 (11) |
C3 | 0.0370 (12) | 0.0431 (12) | 0.0499 (14) | −0.0057 (11) | 0.0066 (10) | −0.0110 (12) |
C8 | 0.0324 (11) | 0.0327 (11) | 0.0390 (11) | −0.0003 (9) | 0.0076 (9) | −0.0061 (9) |
C5 | 0.0437 (12) | 0.0342 (11) | 0.0330 (11) | 0.0061 (10) | 0.0057 (9) | −0.0009 (9) |
C9 | 0.0407 (13) | 0.0318 (12) | 0.0507 (14) | −0.0032 (10) | 0.0080 (11) | 0.0028 (11) |
C4 | 0.0463 (13) | 0.0346 (11) | 0.0376 (11) | 0.0011 (10) | 0.0093 (10) | 0.0044 (10) |
C11 | 0.0335 (11) | 0.0437 (13) | 0.0360 (11) | 0.0000 (10) | 0.0020 (9) | 0.0030 (10) |
C12 | 0.0336 (11) | 0.0305 (10) | 0.0326 (10) | 0.0016 (8) | 0.0046 (8) | −0.0040 (9) |
O2—C12 | 1.259 (3) | C6—C7 | 1.387 (3) |
O1—C12 | 1.264 (3) | C6—C12 | 1.507 (3) |
O5—C5 | 1.206 (3) | C7—C8 | 1.402 (3) |
N1—C2 | 1.364 (3) | C7—H7 | 0.9300 |
N1—C5 | 1.370 (3) | C10—C9 | 1.374 (3) |
N1—H1 | 0.93 (5) | C10—C11 | 1.396 (4) |
N2—C2 | 1.306 (3) | C10—H10 | 0.9300 |
N2—H2A | 0.8600 | C3—H3A | 0.9600 |
N2—H2B | 0.8600 | C3—H3B | 0.9600 |
N3—C2 | 1.323 (3) | C3—H3C | 0.9600 |
N3—C3 | 1.447 (3) | C8—C9 | 1.395 (3) |
N3—C4 | 1.457 (3) | C5—C4 | 1.506 (4) |
N8—C8 | 1.383 (3) | C9—H9 | 0.9300 |
N8—H8A | 0.8600 | C4—H4A | 0.9700 |
N8—H8B | 0.8600 | C4—H4B | 0.9700 |
C6—C11 | 1.385 (3) | C11—H11 | 0.9300 |
C2—N1—C5 | 110.0 (2) | H3A—C3—H3B | 109.5 |
C2—N1—H1 | 123 (2) | N3—C3—H3C | 109.5 |
C5—N1—H1 | 126 (2) | H3A—C3—H3C | 109.5 |
C2—N2—H2A | 120.0 | H3B—C3—H3C | 109.5 |
C2—N2—H2B | 120.0 | N8—C8—C9 | 120.8 (2) |
H2A—N2—H2B | 120.0 | N8—C8—C7 | 121.0 (2) |
C2—N3—C3 | 127.2 (2) | C9—C8—C7 | 118.2 (2) |
C2—N3—C4 | 109.61 (19) | O5—C5—N1 | 126.0 (2) |
C3—N3—C4 | 123.2 (2) | O5—C5—C4 | 127.4 (2) |
C8—N8—H8A | 120.0 | N1—C5—C4 | 106.55 (19) |
C8—N8—H8B | 120.0 | C10—C9—C8 | 120.7 (2) |
H8A—N8—H8B | 120.0 | C10—C9—H9 | 119.6 |
C11—C6—C7 | 120.1 (2) | C8—C9—H9 | 119.6 |
C11—C6—C12 | 120.4 (2) | N3—C4—C5 | 102.54 (19) |
C7—C6—C12 | 119.49 (19) | N3—C4—H4A | 111.3 |
C6—C7—C8 | 120.9 (2) | C5—C4—H4A | 111.3 |
C6—C7—H7 | 119.5 | N3—C4—H4B | 111.3 |
C8—C7—H7 | 119.5 | C5—C4—H4B | 111.3 |
N2—C2—N3 | 127.2 (2) | H4A—C4—H4B | 109.2 |
N2—C2—N1 | 121.6 (2) | C6—C11—C10 | 119.2 (2) |
N3—C2—N1 | 111.17 (19) | C6—C11—H11 | 120.4 |
C9—C10—C11 | 120.9 (2) | C10—C11—H11 | 120.4 |
C9—C10—H10 | 119.6 | O2—C12—O1 | 123.4 (2) |
C11—C10—H10 | 119.6 | O2—C12—C6 | 119.4 (2) |
N3—C3—H3A | 109.5 | O1—C12—C6 | 117.14 (18) |
N3—C3—H3B | 109.5 | ||
C11—C6—C7—C8 | 2.1 (3) | N8—C8—C9—C10 | 177.8 (2) |
C12—C6—C7—C8 | −176.24 (19) | C7—C8—C9—C10 | 0.4 (3) |
C3—N3—C2—N2 | 0.1 (4) | C2—N3—C4—C5 | −2.1 (2) |
C4—N3—C2—N2 | −179.4 (2) | C3—N3—C4—C5 | 178.4 (2) |
C3—N3—C2—N1 | −180.0 (2) | O5—C5—C4—N3 | −177.7 (2) |
C4—N3—C2—N1 | 0.5 (3) | N1—C5—C4—N3 | 2.9 (2) |
C5—N1—C2—N2 | −178.5 (2) | C7—C6—C11—C10 | −1.1 (3) |
C5—N1—C2—N3 | 1.5 (3) | C12—C6—C11—C10 | 177.2 (2) |
C6—C7—C8—N8 | −179.1 (2) | C9—C10—C11—C6 | −0.1 (4) |
C6—C7—C8—C9 | −1.7 (3) | C11—C6—C12—O2 | 2.6 (3) |
C2—N1—C5—O5 | 177.8 (2) | C7—C6—C12—O2 | −179.0 (2) |
C2—N1—C5—C4 | −2.8 (2) | C11—C6—C12—O1 | −175.5 (2) |
C11—C10—C9—C8 | 0.5 (4) | C7—C6—C12—O1 | 2.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.93 (5) | 1.70 (5) | 2.633 (3) | 174 (4) |
N2—H2A···O2i | 0.86 | 2.00 | 2.842 (3) | 166 |
N2—H2B···O2 | 0.86 | 1.97 | 2.823 (3) | 169 |
N8—H8A···O5ii | 0.86 | 2.35 | 3.130 (3) | 152 |
N8—H8B···O1 | 0.86 | 2.36 | 3.157 (3) | 153 |
C3—H3C···O2i | 0.96 | 2.58 | 3.466 (3) | 153 |
Symmetry codes: (i) −x+2, y−1/2, −z; (ii) −x+3, y+3/2, −z+1. |
C7H3N2O6+·C4H8N3O− | F(000) = 672 |
Mr = 325.25 | Dx = 1.568 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.4175 (8) Å | Cell parameters from 3163 reflections |
b = 22.634 (3) Å | θ = 1.8–27.5° |
c = 11.3668 (16) Å | µ = 0.13 mm−1 |
β = 98.696 (3)° | T = 293 K |
V = 1377.8 (3) Å3 | PLATE, colour less |
Z = 4 | 0.28 × 0.28 × 0.08 mm |
Bruker APEXII CCD diffractometer | 2272 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.037 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 27.6°, θmin = 1.8° |
Tmin = 0.586, Tmax = 0.866 | h = −7→7 |
20448 measured reflections | k = −29→29 |
3163 independent reflections | l = −14→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.196 | w = 1/[σ2(Fo2) + (0.0937P)2 + 1.0476P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3163 reflections | Δρmax = 0.25 e Å−3 |
213 parameters | Δρmin = −0.32 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C4 | −0.3894 (5) | 0.67552 (12) | 0.7844 (2) | 0.0424 (6) | |
H4A | −0.558043 | 0.685231 | 0.796735 | 0.051* | |
H4B | −0.392828 | 0.639390 | 0.738318 | 0.051* | |
C5 | −0.2733 (5) | 0.72557 (12) | 0.7240 (2) | 0.0427 (6) | |
C2 | −0.0405 (4) | 0.70851 (10) | 0.9023 (2) | 0.0350 (5) | |
C3 | −0.2620 (5) | 0.62719 (12) | 0.9871 (2) | 0.0483 (6) | |
H3B | −0.129434 | 0.630486 | 1.053120 | 0.072* | |
H3C | −0.262564 | 0.588098 | 0.954290 | 0.072* | |
H3A | −0.419004 | 0.634623 | 1.013773 | 0.072* | |
N8 | 0.9177 (6) | 1.01956 (13) | 0.7037 (3) | 0.0736 (8) | |
C11 | 0.7730 (4) | 0.87486 (11) | 0.9151 (2) | 0.0393 (5) | |
H11 | 0.743572 | 0.843176 | 0.963179 | 0.047* | |
C6 | 0.6068 (4) | 0.88805 (10) | 0.8141 (2) | 0.0375 (5) | |
C8 | 0.8648 (5) | 0.96901 (11) | 0.7773 (2) | 0.0472 (6) | |
C10 | 0.9834 (4) | 0.90935 (11) | 0.9437 (2) | 0.0414 (6) | |
C7 | 0.6512 (5) | 0.93614 (11) | 0.7447 (2) | 0.0437 (6) | |
H6 | 0.538901 | 0.946056 | 0.677449 | 0.052* | |
C9 | 1.0353 (5) | 0.95663 (12) | 0.8765 (2) | 0.0473 (6) | |
H8 | 1.178680 | 0.979244 | 0.896870 | 0.057* | |
N3 | −0.2244 (4) | 0.66995 (9) | 0.89681 (17) | 0.0392 (5) | |
N1 | −0.0656 (4) | 0.74201 (10) | 0.80206 (19) | 0.0413 (5) | |
N2 | 0.1457 (4) | 0.71462 (10) | 0.98893 (19) | 0.0463 (5) | |
H2A | 0.156560 | 0.692065 | 1.050385 | 0.069* | |
H2B | 0.257351 | 0.741190 | 0.984511 | 0.069* | |
C12 | 0.3804 (5) | 0.84969 (12) | 0.7774 (2) | 0.0441 (6) | |
N10 | 1.1616 (4) | 0.89413 (11) | 1.0507 (2) | 0.0552 (6) | |
O5 | −0.3441 (4) | 0.74696 (10) | 0.62776 (17) | 0.0607 (6) | |
O1 | 0.3484 (4) | 0.80812 (10) | 0.8451 (2) | 0.0662 (6) | |
O2 | 0.2439 (4) | 0.86212 (10) | 0.68288 (18) | 0.0627 (6) | |
O6 | 1.3477 (4) | 0.92497 (11) | 1.0742 (2) | 0.0732 (7) | |
O7 | 1.1140 (5) | 0.85160 (13) | 1.1091 (2) | 0.0908 (9) | |
O3 | 0.7738 (7) | 1.02949 (15) | 0.6138 (3) | 0.1128 (12) | |
O4 | 1.1050 (7) | 1.04788 (15) | 0.7360 (3) | 0.1269 (14) | |
H1 | 0.036 (7) | 0.7666 (16) | 0.799 (3) | 0.076 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C4 | 0.0374 (12) | 0.0478 (14) | 0.0387 (13) | −0.0006 (10) | −0.0048 (10) | −0.0040 (11) |
C5 | 0.0398 (13) | 0.0499 (14) | 0.0366 (13) | 0.0072 (11) | 0.0001 (10) | −0.0009 (11) |
C2 | 0.0346 (11) | 0.0369 (12) | 0.0328 (11) | 0.0018 (9) | 0.0026 (9) | −0.0035 (9) |
C3 | 0.0509 (15) | 0.0497 (15) | 0.0431 (14) | −0.0087 (12) | 0.0028 (11) | 0.0045 (12) |
N8 | 0.088 (2) | 0.0612 (17) | 0.0709 (19) | −0.0125 (16) | 0.0086 (16) | 0.0176 (14) |
C11 | 0.0400 (13) | 0.0404 (12) | 0.0362 (12) | 0.0012 (10) | 0.0020 (10) | −0.0023 (10) |
C6 | 0.0370 (12) | 0.0401 (12) | 0.0345 (12) | −0.0001 (10) | 0.0028 (9) | −0.0058 (10) |
C8 | 0.0566 (16) | 0.0379 (13) | 0.0481 (15) | −0.0018 (11) | 0.0106 (12) | −0.0002 (11) |
C10 | 0.0375 (12) | 0.0447 (13) | 0.0388 (13) | 0.0045 (10) | −0.0042 (10) | −0.0078 (10) |
C7 | 0.0483 (14) | 0.0448 (13) | 0.0358 (12) | 0.0058 (11) | −0.0012 (10) | −0.0015 (11) |
C9 | 0.0420 (14) | 0.0453 (14) | 0.0532 (15) | −0.0038 (11) | 0.0034 (12) | −0.0111 (12) |
N3 | 0.0401 (11) | 0.0426 (11) | 0.0327 (10) | −0.0057 (9) | −0.0020 (8) | −0.0009 (8) |
N1 | 0.0398 (11) | 0.0429 (12) | 0.0397 (11) | −0.0031 (9) | 0.0011 (9) | 0.0031 (9) |
N2 | 0.0422 (11) | 0.0560 (13) | 0.0371 (11) | −0.0083 (10) | −0.0054 (9) | −0.0006 (10) |
C12 | 0.0378 (13) | 0.0503 (15) | 0.0436 (14) | −0.0010 (11) | 0.0036 (11) | −0.0110 (12) |
N10 | 0.0452 (13) | 0.0611 (15) | 0.0534 (14) | −0.0011 (11) | −0.0113 (11) | −0.0053 (12) |
O5 | 0.0587 (13) | 0.0767 (14) | 0.0428 (11) | 0.0066 (10) | −0.0048 (9) | 0.0150 (10) |
O1 | 0.0575 (13) | 0.0698 (14) | 0.0686 (14) | −0.0231 (11) | 0.0015 (11) | 0.0062 (11) |
O2 | 0.0508 (12) | 0.0755 (14) | 0.0546 (12) | −0.0006 (10) | −0.0151 (9) | −0.0134 (10) |
O6 | 0.0506 (12) | 0.0799 (15) | 0.0798 (16) | −0.0069 (11) | −0.0200 (11) | −0.0083 (12) |
O7 | 0.0811 (18) | 0.103 (2) | 0.0752 (17) | −0.0186 (15) | −0.0296 (14) | 0.0361 (16) |
O3 | 0.120 (3) | 0.109 (2) | 0.101 (2) | −0.0165 (19) | −0.0119 (19) | 0.0592 (19) |
O4 | 0.142 (3) | 0.107 (2) | 0.123 (3) | −0.075 (2) | −0.010 (2) | 0.041 (2) |
C4—N3 | 1.450 (3) | C11—C6 | 1.381 (3) |
C4—C5 | 1.511 (4) | C11—H11 | 0.9300 |
C4—H4A | 0.9700 | C6—C7 | 1.386 (4) |
C4—H4B | 0.9700 | C6—C12 | 1.509 (3) |
C5—O5 | 1.204 (3) | C8—C9 | 1.374 (4) |
C5—N1 | 1.375 (3) | C8—C7 | 1.378 (4) |
C2—N2 | 1.306 (3) | C10—C9 | 1.369 (4) |
C2—N3 | 1.319 (3) | C10—N10 | 1.475 (3) |
C2—N1 | 1.358 (3) | C7—H6 | 0.9300 |
C3—N3 | 1.447 (3) | C9—H8 | 0.9300 |
C3—H3B | 0.9600 | N1—H1 | 0.79 (4) |
C3—H3C | 0.9600 | N2—H2A | 0.8600 |
C3—H3A | 0.9600 | N2—H2B | 0.8600 |
N8—O3 | 1.209 (4) | C12—O2 | 1.241 (3) |
N8—O4 | 1.210 (4) | C12—O1 | 1.244 (3) |
N8—C8 | 1.471 (4) | N10—O7 | 1.219 (3) |
C11—C10 | 1.379 (3) | N10—O6 | 1.223 (3) |
N3—C4—C5 | 102.84 (19) | C9—C8—C7 | 122.9 (3) |
N3—C4—H4A | 111.2 | C9—C8—N8 | 117.4 (3) |
C5—C4—H4A | 111.2 | C7—C8—N8 | 119.7 (3) |
N3—C4—H4B | 111.2 | C9—C10—C11 | 122.9 (2) |
C5—C4—H4B | 111.2 | C9—C10—N10 | 118.6 (2) |
H4A—C4—H4B | 109.1 | C11—C10—N10 | 118.5 (2) |
O5—C5—N1 | 126.5 (3) | C8—C7—C6 | 118.8 (2) |
O5—C5—C4 | 128.1 (2) | C8—C7—H6 | 120.6 |
N1—C5—C4 | 105.4 (2) | C6—C7—H6 | 120.6 |
N2—C2—N3 | 126.7 (2) | C10—C9—C8 | 116.6 (2) |
N2—C2—N1 | 122.8 (2) | C10—C9—H8 | 121.7 |
N3—C2—N1 | 110.5 (2) | C8—C9—H8 | 121.7 |
N3—C3—H3B | 109.5 | C2—N3—C3 | 126.6 (2) |
N3—C3—H3C | 109.5 | C2—N3—C4 | 110.2 (2) |
H3B—C3—H3C | 109.5 | C3—N3—C4 | 123.3 (2) |
N3—C3—H3A | 109.5 | C2—N1—C5 | 111.0 (2) |
H3B—C3—H3A | 109.5 | C2—N1—H1 | 117 (3) |
H3C—C3—H3A | 109.5 | C5—N1—H1 | 132 (3) |
O3—N8—O4 | 124.2 (3) | C2—N2—H2A | 120.0 |
O3—N8—C8 | 118.0 (3) | C2—N2—H2B | 120.0 |
O4—N8—C8 | 117.8 (3) | H2A—N2—H2B | 120.0 |
C10—C11—C6 | 119.0 (2) | O2—C12—O1 | 125.9 (3) |
C10—C11—H11 | 120.5 | O2—C12—C6 | 117.5 (3) |
C6—C11—H11 | 120.5 | O1—C12—C6 | 116.6 (2) |
C11—C6—C7 | 119.7 (2) | O7—N10—O6 | 124.6 (3) |
C11—C6—C12 | 120.4 (2) | O7—N10—C10 | 117.9 (2) |
C7—C6—C12 | 119.9 (2) | O6—N10—C10 | 117.5 (3) |
N3—C4—C5—O5 | −179.6 (3) | N2—C2—N3—C3 | 1.7 (4) |
N3—C4—C5—N1 | 0.7 (3) | N1—C2—N3—C3 | −179.4 (2) |
C10—C11—C6—C7 | −1.3 (4) | N2—C2—N3—C4 | −177.8 (2) |
C10—C11—C6—C12 | 177.4 (2) | N1—C2—N3—C4 | 1.1 (3) |
O3—N8—C8—C9 | 177.2 (3) | C5—C4—N3—C2 | −1.1 (3) |
O4—N8—C8—C9 | −1.4 (5) | C5—C4—N3—C3 | 179.4 (2) |
O3—N8—C8—C7 | −2.4 (5) | N2—C2—N1—C5 | 178.4 (2) |
O4—N8—C8—C7 | 179.0 (4) | N3—C2—N1—C5 | −0.6 (3) |
C6—C11—C10—C9 | 0.3 (4) | O5—C5—N1—C2 | −179.8 (3) |
C6—C11—C10—N10 | −179.0 (2) | C4—C5—N1—C2 | −0.1 (3) |
C9—C8—C7—C6 | −0.7 (4) | C11—C6—C12—O2 | −176.7 (2) |
N8—C8—C7—C6 | 178.9 (2) | C7—C6—C12—O2 | 2.0 (4) |
C11—C6—C7—C8 | 1.4 (4) | C11—C6—C12—O1 | 3.0 (4) |
C12—C6—C7—C8 | −177.3 (2) | C7—C6—C12—O1 | −178.3 (2) |
C11—C10—C9—C8 | 0.4 (4) | C9—C10—N10—O7 | −179.4 (3) |
N10—C10—C9—C8 | 179.7 (2) | C11—C10—N10—O7 | 0.0 (4) |
C7—C8—C9—C10 | −0.2 (4) | C9—C10—N10—O6 | 0.2 (4) |
N8—C8—C9—C10 | −179.8 (2) | C11—C10—N10—O6 | 179.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.79 (4) | 1.94 (4) | 2.679 (3) | 157 (3) |
N2—H2B···O1 | 0.86 | 2.30 | 2.983 (3) | 137 |
N2—H2B···O5i | 0.86 | 2.51 | 3.093 (3) | 125 |
N2—H2A···O2ii | 0.86 | 1.94 | 2.794 (3) | 169 |
C3—H3B···O2ii | 0.96 | 2.32 | 3.268 (3) | 168 |
C4—H4B···O4iii | 0.97 | 2.58 | 3.299 (4) | 131 |
Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2. |
Creatinine salts | Protonation at | Unit cell (Å, °) and space group | Centro/Noncentrosymmetric | Primary interaction between | Graph-set motif | Motif type | Secondary interaction between | Graph-set motif | Motif type | Supramolecular architecture |
Creatininium chloride | N1 | Monoclinic, P21/n; a = 8.4617 (2), b = 7.7073 (2), c = 10.2215 (3), β = 98.369 (2) | Centrosymmetric | Pair of N—H···Cl | R42(8) | III | C—H···Cl | R21(7), R42(12) | XVIII and XIX | Chain |
Creatininium bromide | N1 | Monoclinic, P21/n a = 8.7252 (4), b = 7.7772 (4), c = 10.7406 (5), β = 97.969 (1)° | Centrosymmetric | Pair of N—H···Br | R42(8) | III | C—H···Br | R21(7), R42(12) | XVIII and XIX | Chain |
Creatininium nitrate | N1 | Orthorhombic, Pbca; a = 16.6509 (3), b = 9.7336 (2), c = 8.9989 (3) | Centrosymmetric | N—H···O | R44(16) | X | Chain | |||
Creatininium phosphite | N1 | Monoclinic, P21/c; a = 8.8083 (11), b = 6.6316 (9), c = 15.068 (2), β = 99.539 (4) | Centrosymmetric | Pair of N—H···O Fork-like dimer, Pair of N—H···O | R22(8) | III | O—H···O Fork-like dimer b/w acid | R22(8), R42(8) | XIII and XIV | Chain |
Creatinium perchlorate | N1 | Monoclinic, P21/c; a = 5.8023 (3), b = 20.7782 (13), c = 7.3250 (4), β = 107.947 (4) | Centrosymmetric | Pair of N—H···O | R21(6) | V | N—H···O | R24(8) | XX | |
Bis(creatininium) sulfate | N1 | Monoclinic, P21/c; a = 12.469 (6), b = 7.560 (3), c = 14.382 (9), β = 97.347 (11) | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | IV | N—H···O | C22(7) | XXV | Grid |
Creatininium benzenesulfonate | N1 | Monoclinic, P21; a = 7.0344 (12), b = 11.4987 (18), c = 7.8380 (11), β = 102.477 (4) | Noncentrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | IV | C—H···N | Zigzag chain | ||
Creatininium 2-chloroacetate | N1 | Monoclinic, P21/n; a = 5.7993 (8), b = 13.934 (2), c = 11.2205 (16), β = 95.326 (2) | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | N—H···O | R42(8) | XIV | Sheet |
Creatininium cinnamate | N1 | Monoclinic, P21/c; a = 9.1680 (8), b = 11.3391 (11), c = 12.7070 (12), β = 104.578 (2) | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | N—H···O | C22(6) | XXVI | Linear chain |
Creatininium benzoate | N1 | Monoclinic, P21/c; a = 8.5574 (5), b = 6.2094 (4), c = 22.0169 (14), β = 99.904 (1) | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | C—H···O, N—H···O | R21(7) | XXII | Zigzag chain |
Creatininium benzoate | N1 | Orthorhombic, SG?; a = 6.9095 (5), b = 10.2699 (7), c = 16.4105 (11) | Noncentrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | C—H···O, N—H···O | R21(7) | XXII | Zigzag chain |
Creatininium 4-nitrobenzoate | N1 | Orthorhombic, SG?; a = 5.747 (3), b = 9.092 (2), c = 24.148 (6) | Noncentrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | Chain | |||
Creatininium 3,5-dinitrobenzoate | N1 | Monoclinic, P21/c; a = 5.4175 (8), b = 22.634 (3), c = 11.3668 (16) | Centrosymmetric | Pair of N—H···O | R21(6) | VII | C—H···O and N—H···O | R21(7) | IX | Chain |
Creatininium 3-aminobenzoate | N1 | Monoclinic, P21; a = 7.9887 (4), b = 6.6098 (3), c = 11.4753 (6), β = 102.080 (2) | Noncentrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | N—H···O, C—H···O | R21(7) | IX | Chain |
Creatininium hydrogen oxalate monohydrate | N1 | Orthorhombic, Pnma; a = 9.1728 (7), b = 6.3520 (5), c = 16.6567 (12) | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | Pair of O—H···O b/w anions | R12(7) | XV | Sheet |
Creatininium succinate | N1 | Orthorhombic, F2dd; a = 5.534 (3), b = 14.278 (1), c = 40.131 (2) | Noncentrosymmetric | |||||||
Bis(creatininium) fumarate fumaric acid | N2 | Monoclinic, P21/c; a = 5.902 (2), b = 21.833 (9), c = 7.7752 (6) | Centrosymmetric | Pair of N—H···O | R21(6) | VII | Pair of O—H···O | R12(4) | XXI | |
Creatininium hydrogen maleate | N14 | Monoclinic, P21/n; a = 5.6271 (4) b = 24.8915 (17), c = 7.7752 (6), β = 108.69 (2) | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | Anion intramolecular O—H···O; N—H···O b/w cation and anion | S(7), R64(16) | XV | |
Creatininium L-tartrate monohydrate | N1 | Orthorhombic, P212121 | Noncentrosymmetric | N—H···O and O—H···O | R32(8) | VIII | ||||
Creatininium phthalate | N1 | Triclinic, P1; a = 7.7322 (7), b = 9.9601 (9), c = 10.0821 (9), α = 107.173 (1), β = 11.892 (1), γ = 103.843 (1) | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | N—H···O, C—H···O | R21(7), R64(16), S(7) | XXII and XVI | Sheet |
Bis(creatininium) 3-nitrophthalate monohydrate | N1 | Monoclinic, P21/c; a = 7.6682 (3), b = 16.5504 (6), c = 16.2358 (7), β = 93.775 (1) | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I and II | O—H···O and pair of C—H···O, N—H···O and O—H···O | |||
Creatininium salicylate | N1 | Monoclinic, P21/n; a = 7.6782 (10), b = 12.4991 (16), c = 12.4268 (16), β = 101.005 (2) | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | Intramolecular O—H···O in anion | S(7) | XVI | Chain |
Creatinine diphenic acid monohydrate | N1 | Monoclinic, P21/c; a = 15.673, b = 7.2975, c = 17.120, β = 115.878 | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | O—H···O | |||
Creatinine pyrazine-2,3-dicarboxylic acid | N1 | Monoclinic, Pc; a = 3.9677 (6), b = 11.567 (2), c = 13.290 (2), β = 94.53 (1) | Noncentrosymmetric | Pair of N—H···O | R22(8) | I | N—H···O | R21(6) | XVII | Chain |
Creatininium gallate trihydrate | N1 | Monoclinic, P21/c; a = 6.6373 (1); b = 15.7350 (2); c = 14.1111 (1); β = 96.156 (1) | Centrosymmetric | Pair of N—H···O Fork-like dimer | R22(8) | I | O—H···O and C—H···O | Chain | ||
Creatininium 5-(2,4-dinitrophenyl)-1,3-dimethylbarbiturate monohydrate | N1 | Monoclinic, P21/n; a = 12.6926 (3), b = 7.3093 (2), c = 20.6213 (5), β = 100.420 (4) | Centrosymmetric | N—H···O hydrogen bond | R21(7) | IX | O—H···O and N—H···O between anions | R66(24) | XXIV | Sheet |
Salt (I) | |||
All···All | 100% | N···H/H···N | 5.8 |
Br···H/H···Br | 32.7 | C···H/H···C | 4.0 |
O···H/H···O | 19.3 | H···H | 31.0 |
Salt (II) | |||
All···All | 100 | N···H/H···N | 4.8 |
O···H/H···O | 28.9 | H···H | 41.8% |
C···H/H···C | 16.9 | C···C | 2.4 |
Salt (III) | |||
All···All | 100 | N···H/H···N | 4.2 |
O···H/H···O | 51.4 | H···H | 13.2 |
C···H/H···C | 10.3 |
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