
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617002906/bp5095sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2052520617002906/bp5095Isup2.hkl |
![]() | Portable Document Format (PDF) file https://doi.org/10.1107/S2052520617002906/bp5095sup3.pdf |
CCDC reference: 1403424
Program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
2(C4H9N2O3)·2(C4HO4)·H2O | Dx = 1.574 Mg m−3 |
Mr = 510.38 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P21212 | Cell parameters from 2347 reflections |
a = 19.7808 (13) Å | θ = 3.4–29.2° |
b = 8.9659 (6) Å | µ = 0.14 mm−1 |
c = 6.0713 (4) Å | T = 293 K |
V = 1076.75 (12) Å3 | Block, colorless |
Z = 2 | 0.5 × 0.5 × 0.5 mm |
F(000) = 532 |
Xcalibur, Sapphire3 diffractometer | 2394 reflections with I > 2σ(I) |
ω scans | Rint = 0.019 |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 29.2°, θmin = 3.4° |
Tmin = 0.850, Tmax = 1.000 | h = −24→26 |
5216 measured reflections | k = −11→4 |
2531 independent reflections | l = −7→7 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.041P)2 + 0.176P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max = 0.001 |
wR(F2) = 0.086 | Δρmax = 0.26 e Å−3 |
S = 1.09 | Δρmin = −0.16 e Å−3 |
2531 reflections | Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
167 parameters | Extinction coefficient: 0.018 (4) |
0 restraints | Absolute structure: Flack x determined using 882 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (4) |
Hydrogen site location: mixed |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O4 | −0.44943 (9) | −0.83943 (18) | −0.4070 (2) | 0.0354 (4) | |
O2 | −0.39987 (11) | −1.0128 (2) | 0.2833 (3) | 0.0452 (5) | |
H2 | −0.4133 | −0.9544 | 0.3776 | 0.068* | |
O1 | −0.47779 (8) | −0.72246 (18) | 0.0954 (3) | 0.0338 (4) | |
O3 | −0.36888 (9) | −1.12265 (19) | −0.2132 (3) | 0.0378 (4) | |
C1 | −0.44708 (10) | −0.8293 (2) | 0.0092 (3) | 0.0235 (4) | |
C4 | −0.43391 (11) | −0.8815 (2) | −0.2203 (3) | 0.0240 (4) | |
C2 | −0.41196 (11) | −0.9579 (2) | 0.0882 (3) | 0.0270 (4) | |
C3 | −0.39708 (11) | −1.0131 (2) | −0.1306 (3) | 0.0254 (4) | |
O5 | −0.34959 (8) | −0.55773 (19) | −0.3119 (3) | 0.0328 (4) | |
N1 | −0.42409 (9) | −0.3422 (2) | −0.5022 (3) | 0.0277 (4) | |
H1A | −0.4548 | −0.2909 | −0.5778 | 0.033* | |
H1B | −0.3926 | −0.2801 | −0.4516 | 0.033* | |
H1C | −0.4440 | −0.3881 | −0.3896 | 0.033* | |
C5 | −0.34832 (10) | −0.5579 (2) | −0.5101 (3) | 0.0243 (4) | |
O7 | −0.27338 (8) | −0.3096 (2) | −0.5702 (3) | 0.0388 (4) | |
C6 | −0.39223 (10) | −0.4543 (2) | −0.6481 (3) | 0.0223 (4) | |
H6 | −0.4286 | −0.5147 | −0.7115 | 0.027* | |
O6 | −0.31313 (9) | −0.6483 (2) | −0.6345 (3) | 0.0362 (4) | |
H6A | −0.2883 | −0.6994 | −0.5569 | 0.054* | |
C8 | −0.29175 (11) | −0.3008 (3) | −0.7648 (4) | 0.0284 (5) | |
C7 | −0.35520 (10) | −0.3801 (3) | −0.8382 (3) | 0.0276 (4) | |
H7A | −0.3434 | −0.4552 | −0.9466 | 0.033* | |
H7B | −0.3852 | −0.3088 | −0.9084 | 0.033* | |
N2 | −0.25854 (12) | −0.2247 (3) | −0.9142 (4) | 0.0536 (7) | |
H2A | −0.2222 | −0.1780 | −0.8788 | 0.064* | |
H2B | −0.2731 | −0.2216 | −1.0475 | 0.064* | |
O8 | −0.5000 | −0.5000 | −0.1963 (4) | 0.0299 (5) | |
H8 | −0.4834 (19) | −0.557 (4) | −0.137 (6) | 0.075 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0547 (10) | 0.0333 (8) | 0.0182 (7) | 0.0123 (7) | −0.0039 (7) | 0.0013 (7) |
O2 | 0.0849 (14) | 0.0347 (9) | 0.0161 (8) | 0.0254 (9) | −0.0033 (8) | −0.0006 (7) |
O1 | 0.0497 (9) | 0.0273 (8) | 0.0244 (7) | 0.0135 (7) | −0.0007 (7) | −0.0031 (7) |
O3 | 0.0575 (11) | 0.0317 (8) | 0.0242 (8) | 0.0175 (8) | −0.0039 (7) | −0.0066 (7) |
C1 | 0.0322 (10) | 0.0210 (9) | 0.0172 (9) | 0.0011 (8) | −0.0021 (7) | −0.0001 (8) |
C4 | 0.0330 (10) | 0.0210 (9) | 0.0179 (9) | 0.0015 (8) | −0.0005 (8) | −0.0019 (8) |
C2 | 0.0403 (11) | 0.0224 (10) | 0.0182 (9) | 0.0046 (8) | −0.0026 (9) | −0.0019 (8) |
C3 | 0.0349 (11) | 0.0240 (10) | 0.0171 (9) | 0.0016 (8) | −0.0027 (8) | −0.0010 (8) |
O5 | 0.0385 (9) | 0.0380 (9) | 0.0219 (7) | 0.0104 (7) | 0.0002 (7) | −0.0003 (7) |
N1 | 0.0278 (8) | 0.0245 (9) | 0.0309 (9) | 0.0035 (6) | 0.0020 (7) | −0.0019 (8) |
C5 | 0.0232 (9) | 0.0239 (10) | 0.0258 (10) | 0.0009 (7) | 0.0005 (8) | −0.0026 (9) |
O7 | 0.0420 (9) | 0.0456 (10) | 0.0287 (8) | −0.0204 (8) | −0.0074 (7) | 0.0059 (8) |
C6 | 0.0226 (9) | 0.0213 (9) | 0.0230 (10) | 0.0003 (7) | −0.0022 (7) | −0.0044 (8) |
O6 | 0.0446 (9) | 0.0394 (10) | 0.0245 (8) | 0.0209 (7) | −0.0024 (6) | −0.0039 (7) |
C8 | 0.0282 (10) | 0.0319 (11) | 0.0251 (10) | −0.0002 (9) | 0.0016 (8) | 0.0027 (9) |
C7 | 0.0324 (11) | 0.0304 (11) | 0.0199 (9) | 0.0005 (9) | −0.0029 (8) | −0.0002 (9) |
N2 | 0.0452 (12) | 0.0818 (19) | 0.0338 (11) | −0.0240 (12) | −0.0022 (10) | 0.0179 (13) |
O8 | 0.0329 (12) | 0.0291 (12) | 0.0278 (12) | 0.0085 (10) | 0.000 | 0.000 |
O4—C4 | 1.234 (2) | O5—C5 | 1.204 (3) |
O2—C2 | 1.304 (3) | N1—C6 | 1.481 (3) |
O1—C1 | 1.249 (3) | C5—C6 | 1.523 (3) |
O3—C3 | 1.236 (3) | C5—O6 | 1.308 (3) |
C1—C4 | 1.493 (3) | O7—C8 | 1.238 (3) |
C1—C2 | 1.429 (3) | C6—C7 | 1.520 (3) |
C4—C3 | 1.489 (3) | C8—C7 | 1.510 (3) |
C2—C3 | 1.448 (3) | C8—N2 | 1.311 (3) |
O1—C1—C4 | 135.74 (19) | C2—C3—C4 | 87.99 (16) |
O1—C1—C2 | 135.6 (2) | O5—C5—C6 | 122.5 (2) |
C2—C1—C4 | 88.59 (16) | O5—C5—O6 | 126.1 (2) |
O4—C4—C1 | 135.92 (18) | O6—C5—C6 | 111.34 (17) |
O4—C4—C3 | 134.41 (19) | N1—C6—C5 | 109.14 (16) |
C3—C4—C1 | 89.58 (15) | N1—C6—C7 | 111.23 (17) |
O2—C2—C1 | 134.30 (19) | C7—C6—C5 | 114.20 (16) |
O2—C2—C3 | 131.79 (18) | O7—C8—C7 | 119.72 (19) |
C1—C2—C3 | 93.83 (17) | O7—C8—N2 | 123.1 (2) |
O3—C3—C4 | 134.58 (19) | N2—C8—C7 | 117.2 (2) |
O3—C3—C2 | 137.38 (19) | C8—C7—C6 | 112.48 (17) |