Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617017909/sk3677sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017909/sk3677beta-ala_DL-tart_IIsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017909/sk3677beta-ala_DL-tart_IIIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017909/sk3677GABA_DL-tart_IVsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017909/sk3677DL-AABA_DL-tart_Vsup5.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617017909/sk3677sup6.pdf | |
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617017909/sk3677sup7.cif |
CCDC references: 1583099; 1544294; 1540017; 1585722
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: SHELXS97 (Sheldrick, 2008) for beta-ala_DL-tart_II; SHELXS (Sheldrick, 2008) for beta-ala_DL-tart_III; SHELXT (Sheldrick, 2015a) for DL-AABA_DL-tart_V. For all structures, program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C3H7NO2·C4H6O6 | F(000) = 504 |
Mr = 239.18 | Dx = 1.626 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 4.88596 (17) Å | Cell parameters from 4805 reflections |
b = 9.4420 (2) Å | θ = 1.9–27.7° |
c = 21.7319 (6) Å | µ = 0.15 mm−1 |
β = 103.021 (3)° | T = 293 K |
V = 976.78 (5) Å3 | Block, colourless |
Z = 4 | 0.86 × 0.12 × 0.08 mm |
Agilent Xcalibur Ruby Gemini ultra diffractometer | 1996 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1889 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.9° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→11 |
Tmin = 0.791, Tmax = 1.000 | l = −27→27 |
12471 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
wR(F2) = 0.072 | w = 1/[σ2(Fo2) + (0.0381P)2 + 0.1523P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1996 reflections | Δρmax = 0.21 e Å−3 |
151 parameters | Δρmin = −0.17 e Å−3 |
0 restraints |
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. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
O4 | 0.2841 (2) | 0.64658 (11) | 0.00115 (6) | 0.0347 (3) | |
H4 | 0.366835 | 0.584657 | 0.024619 | 0.042* | |
O3 | 0.7265 (2) | 0.61737 (11) | −0.06679 (5) | 0.0292 (2) | |
H3 | 0.891706 | 0.628304 | −0.048873 | 0.035* | |
O6 | 0.8728 (3) | 0.87259 (11) | 0.05260 (5) | 0.0376 (3) | |
H6 | 0.996236 | 0.876041 | 0.085139 | 0.045* | |
O1 | 0.1750 (3) | 0.86171 (12) | −0.11791 (5) | 0.0400 (3) | |
H1 | 0.044420 | 0.864370 | −0.149112 | 0.048* | |
C4 | 0.7182 (3) | 0.76069 (15) | 0.05370 (6) | 0.0257 (3) | |
C3 | 0.4722 (3) | 0.75774 (15) | −0.00302 (7) | 0.0250 (3) | |
H3A | 0.370268 | 0.847456 | −0.004176 | 0.030* | |
O5 | 0.7605 (3) | 0.66850 (13) | 0.09322 (5) | 0.0406 (3) | |
O7 | 0.7307 (2) | 0.58365 (11) | 0.30080 (5) | 0.0311 (3) | |
O8 | 0.7092 (3) | 0.38062 (11) | 0.35126 (5) | 0.0401 (3) | |
O2 | 0.2879 (2) | 0.66539 (11) | −0.16318 (5) | 0.0333 (3) | |
C2 | 0.5776 (3) | 0.74545 (14) | −0.06436 (6) | 0.0227 (3) | |
H2 | 0.702772 | 0.825350 | −0.066754 | 0.027* | |
C5 | 0.6129 (3) | 0.46909 (14) | 0.30895 (6) | 0.0236 (3) | |
C1 | 0.3293 (3) | 0.75113 (14) | −0.12109 (7) | 0.0229 (3) | |
C6 | 0.3351 (3) | 0.43399 (15) | 0.26446 (7) | 0.0252 (3) | |
H6A | 0.361525 | 0.352096 | 0.239470 | 0.030* | |
H6B | 0.201323 | 0.407929 | 0.289377 | 0.030* | |
N1 | 0.3915 (3) | 0.58754 (13) | 0.17552 (6) | 0.0334 (3) | |
H1A | 0.325984 | 0.664811 | 0.153656 | 0.050* | |
H1B | 0.390468 | 0.515443 | 0.149088 | 0.050* | |
H1C | 0.566431 | 0.603181 | 0.197164 | 0.050* | |
C7 | 0.2106 (3) | 0.55276 (16) | 0.22007 (7) | 0.0269 (3) | |
H7A | 0.025827 | 0.524954 | 0.196286 | 0.032* | |
H7B | 0.188929 | 0.636301 | 0.244517 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0258 (6) | 0.0374 (6) | 0.0372 (6) | −0.0056 (5) | −0.0006 (5) | 0.0099 (5) |
O3 | 0.0207 (5) | 0.0295 (5) | 0.0336 (6) | 0.0058 (4) | −0.0016 (5) | −0.0020 (4) |
O6 | 0.0412 (7) | 0.0329 (6) | 0.0307 (6) | −0.0072 (5) | −0.0088 (5) | −0.0021 (5) |
O1 | 0.0421 (7) | 0.0389 (6) | 0.0300 (6) | 0.0191 (6) | −0.0107 (5) | −0.0073 (5) |
C4 | 0.0262 (8) | 0.0275 (7) | 0.0221 (7) | 0.0022 (6) | 0.0028 (6) | −0.0025 (6) |
C3 | 0.0233 (7) | 0.0250 (7) | 0.0247 (7) | −0.0005 (6) | 0.0012 (6) | 0.0003 (6) |
O5 | 0.0439 (7) | 0.0447 (7) | 0.0285 (6) | −0.0035 (6) | −0.0019 (5) | 0.0113 (5) |
O7 | 0.0262 (6) | 0.0301 (5) | 0.0317 (6) | −0.0083 (4) | −0.0046 (5) | 0.0018 (5) |
O8 | 0.0394 (7) | 0.0309 (6) | 0.0386 (6) | −0.0017 (5) | −0.0153 (6) | 0.0095 (5) |
O2 | 0.0324 (6) | 0.0318 (6) | 0.0304 (6) | 0.0031 (5) | −0.0042 (5) | −0.0077 (5) |
C2 | 0.0214 (8) | 0.0211 (6) | 0.0236 (7) | −0.0004 (5) | 0.0007 (6) | −0.0005 (5) |
C5 | 0.0228 (7) | 0.0225 (6) | 0.0231 (7) | 0.0026 (6) | −0.0001 (6) | −0.0032 (5) |
C1 | 0.0226 (8) | 0.0221 (7) | 0.0226 (7) | −0.0001 (6) | 0.0021 (6) | 0.0022 (5) |
C6 | 0.0236 (7) | 0.0253 (7) | 0.0240 (7) | −0.0025 (6) | −0.0003 (6) | 0.0020 (6) |
N1 | 0.0447 (9) | 0.0279 (6) | 0.0291 (7) | 0.0077 (6) | 0.0117 (6) | 0.0038 (5) |
C7 | 0.0218 (7) | 0.0302 (8) | 0.0260 (8) | 0.0005 (6) | −0.0005 (6) | 0.0007 (6) |
O4—H4 | 0.8200 | O2—C1 | 1.2041 (17) |
O4—C3 | 1.4112 (18) | C2—H2 | 0.9800 |
O3—H3 | 0.8200 | C2—C1 | 1.5231 (19) |
O3—C2 | 1.4185 (17) | C5—C6 | 1.515 (2) |
O6—H6 | 0.8200 | C6—H6A | 0.9700 |
O6—C4 | 1.3024 (18) | C6—H6B | 0.9700 |
O1—H1 | 0.8200 | C6—C7 | 1.515 (2) |
O1—C1 | 1.2990 (17) | N1—H1A | 0.8900 |
C4—C3 | 1.516 (2) | N1—H1B | 0.8900 |
C4—O5 | 1.2075 (17) | N1—H1C | 0.8900 |
C3—H3A | 0.9800 | N1—C7 | 1.487 (2) |
C3—C2 | 1.5381 (19) | C7—H7A | 0.9700 |
O7—C5 | 1.2564 (17) | C7—H7B | 0.9700 |
O8—C5 | 1.2528 (17) | ||
C3—O4—H4 | 109.5 | O1—C1—C2 | 110.56 (12) |
C2—O3—H3 | 109.5 | O2—C1—O1 | 125.49 (14) |
C4—O6—H6 | 109.5 | O2—C1—C2 | 123.93 (13) |
C1—O1—H1 | 109.5 | C5—C6—H6A | 108.6 |
O6—C4—C3 | 110.93 (12) | C5—C6—H6B | 108.6 |
O5—C4—O6 | 126.21 (14) | H6A—C6—H6B | 107.6 |
O5—C4—C3 | 122.86 (13) | C7—C6—C5 | 114.71 (12) |
O4—C3—C4 | 111.72 (12) | C7—C6—H6A | 108.6 |
O4—C3—H3A | 108.1 | C7—C6—H6B | 108.6 |
O4—C3—C2 | 110.46 (12) | H1A—N1—H1B | 109.5 |
C4—C3—H3A | 108.1 | H1A—N1—H1C | 109.5 |
C4—C3—C2 | 110.32 (12) | H1B—N1—H1C | 109.5 |
C2—C3—H3A | 108.1 | C7—N1—H1A | 109.5 |
O3—C2—C3 | 111.79 (11) | C7—N1—H1B | 109.5 |
O3—C2—H2 | 108.8 | C7—N1—H1C | 109.5 |
O3—C2—C1 | 108.75 (11) | C6—C7—H7A | 109.3 |
C3—C2—H2 | 108.8 | C6—C7—H7B | 109.3 |
C1—C2—C3 | 109.74 (11) | N1—C7—C6 | 111.44 (12) |
C1—C2—H2 | 108.8 | N1—C7—H7A | 109.3 |
O7—C5—C6 | 118.12 (12) | N1—C7—H7B | 109.3 |
O8—C5—O7 | 124.70 (13) | H7A—C7—H7B | 108.0 |
O8—C5—C6 | 117.18 (12) | ||
O4—C3—C2—O3 | −61.53 (15) | C3—C2—C1—O1 | 52.44 (15) |
O4—C3—C2—C1 | 59.22 (14) | C3—C2—C1—O2 | −128.76 (15) |
O3—C2—C1—O1 | 175.01 (13) | O5—C4—C3—O4 | 8.0 (2) |
O3—C2—C1—O2 | −6.18 (19) | O5—C4—C3—C2 | −115.30 (16) |
O6—C4—C3—O4 | −173.00 (13) | O7—C5—C6—C7 | −8.10 (19) |
O6—C4—C3—C2 | 63.73 (15) | O8—C5—C6—C7 | 172.23 (14) |
C4—C3—C2—O3 | 62.47 (14) | C5—C6—C7—N1 | 64.50 (16) |
C4—C3—C2—C1 | −176.77 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3i | 0.82 | 2.21 | 2.8778 (15) | 139 |
O3—H3···O4ii | 0.82 | 1.99 | 2.8048 (15) | 175 |
O6—H6···O8iii | 0.82 | 1.76 | 2.5728 (15) | 173 |
O1—H1···O7iv | 0.82 | 1.74 | 2.5240 (16) | 160 |
N1—H1A···O8v | 0.89 | 2.05 | 2.8477 (17) | 149 |
N1—H1C···O7 | 0.89 | 2.22 | 2.8508 (17) | 127 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+2, y+1/2, −z+1/2; (iv) x−1, −y+3/2, z−1/2; (v) −x+1, y+1/2, −z+1/2. |
C6H15N2O4+·C8H11O12− | Z = 1 |
Mr = 478.37 | F(000) = 252 |
Triclinic, P1 | Dx = 1.655 Mg m−3 |
a = 4.9216 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.5949 (6) Å | Cell parameters from 2996 reflections |
c = 12.1187 (7) Å | θ = 1.8–27.8° |
α = 108.610 (6)° | µ = 0.15 mm−1 |
β = 97.243 (5)° | T = 293 K |
γ = 92.752 (5)° | Block, colourless |
V = 479.82 (6) Å3 | 0.3 × 0.14 × 0.12 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1962 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1626 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.8° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −10→10 |
Tmin = 0.965, Tmax = 1.000 | l = −15→15 |
6002 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0499P)2 + 0.2341P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
1962 reflections | Δρmax = 0.25 e Å−3 |
154 parameters | Δρmin = −0.27 e Å−3 |
0 restraints |
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 | ||
O3 | 0.2694 (3) | 0.99355 (16) | 0.13191 (12) | 0.0259 (3) | |
O6 | 0.1929 (3) | 0.59451 (15) | 0.06566 (11) | 0.0291 (3) | |
O4 | 0.7460 (2) | 0.84652 (15) | 0.02993 (11) | 0.0265 (3) | |
H4 | 0.901138 | 0.877581 | 0.066836 | 0.032* | |
O1 | 0.8831 (3) | 0.97686 (15) | 0.31713 (11) | 0.0294 (3) | |
H1 | 0.998520 | 1.049321 | 0.361066 | 0.035* | |
O5 | 0.3221 (3) | 0.63581 (17) | −0.09339 (11) | 0.0332 (3) | |
O8 | 0.4355 (3) | 0.85520 (15) | 0.44061 (12) | 0.0337 (3) | |
O2 | 0.6977 (3) | 1.18792 (16) | 0.27615 (14) | 0.0404 (4) | |
C3 | 0.5851 (3) | 0.77953 (19) | 0.09600 (14) | 0.0188 (4) | |
H3A | 0.701002 | 0.719059 | 0.136726 | 0.023* | |
C2 | 0.4658 (3) | 0.91587 (19) | 0.18716 (14) | 0.0194 (4) | |
H2 | 0.373911 | 0.866092 | 0.236630 | 0.023* | |
N1 | 0.2081 (3) | 0.36309 (18) | 0.23089 (14) | 0.0285 (4) | |
H1A | 0.314904 | 0.365175 | 0.177231 | 0.043* | |
H1B | 0.033510 | 0.338485 | 0.196660 | 0.043* | |
H1C | 0.257938 | 0.287190 | 0.263126 | 0.043* | |
O7 | 0.7675 (3) | 0.77751 (18) | 0.54905 (14) | 0.0481 (4) | |
C5 | 0.5866 (4) | 0.7502 (2) | 0.46338 (16) | 0.0260 (4) | |
C1 | 0.6937 (3) | 1.0436 (2) | 0.26560 (14) | 0.0213 (4) | |
C4 | 0.3501 (3) | 0.6606 (2) | 0.01279 (15) | 0.0202 (4) | |
C7 | 0.2382 (4) | 0.5271 (2) | 0.32363 (16) | 0.0263 (4) | |
H7A | 0.136349 | 0.522122 | 0.386131 | 0.032* | |
H7B | 0.162704 | 0.607591 | 0.290620 | 0.032* | |
C6 | 0.5368 (4) | 0.5792 (2) | 0.37317 (17) | 0.0288 (4) | |
H6A | 0.638730 | 0.575852 | 0.309083 | 0.035* | |
H6B | 0.607583 | 0.500798 | 0.409362 | 0.035* | |
H6 | 0.000000 | 0.500000 | 0.000000 | 0.091 (15)* | |
H8 | 0.500000 | 1.000000 | 0.500000 | 0.122 (19)* | |
H3 | 0.319 (7) | 1.027 (4) | 0.086 (3) | 0.093 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0200 (6) | 0.0286 (7) | 0.0282 (7) | 0.0037 (5) | −0.0019 (5) | 0.0100 (6) |
O6 | 0.0252 (7) | 0.0309 (7) | 0.0275 (7) | −0.0118 (5) | −0.0017 (5) | 0.0086 (6) |
O4 | 0.0186 (6) | 0.0319 (7) | 0.0278 (7) | −0.0072 (5) | 0.0034 (5) | 0.0092 (5) |
O1 | 0.0245 (7) | 0.0267 (7) | 0.0295 (7) | −0.0029 (5) | −0.0103 (5) | 0.0050 (5) |
O5 | 0.0260 (7) | 0.0457 (8) | 0.0215 (7) | −0.0083 (6) | −0.0025 (5) | 0.0062 (6) |
O8 | 0.0428 (8) | 0.0224 (7) | 0.0303 (7) | 0.0035 (6) | −0.0040 (6) | 0.0044 (6) |
O2 | 0.0362 (8) | 0.0218 (7) | 0.0553 (10) | −0.0054 (6) | −0.0131 (7) | 0.0102 (6) |
C3 | 0.0156 (8) | 0.0189 (8) | 0.0216 (8) | −0.0020 (6) | −0.0008 (6) | 0.0078 (6) |
C2 | 0.0175 (8) | 0.0194 (8) | 0.0202 (8) | −0.0014 (6) | −0.0010 (6) | 0.0067 (6) |
N1 | 0.0238 (8) | 0.0234 (8) | 0.0306 (8) | −0.0019 (6) | −0.0038 (6) | 0.0017 (6) |
O7 | 0.0507 (9) | 0.0316 (8) | 0.0470 (9) | −0.0099 (7) | −0.0270 (7) | 0.0068 (7) |
C5 | 0.0253 (9) | 0.0241 (9) | 0.0256 (9) | −0.0053 (7) | −0.0013 (7) | 0.0069 (7) |
C1 | 0.0191 (8) | 0.0234 (9) | 0.0187 (8) | −0.0010 (7) | 0.0002 (7) | 0.0047 (7) |
C4 | 0.0162 (8) | 0.0185 (8) | 0.0237 (9) | 0.0010 (6) | −0.0003 (6) | 0.0051 (7) |
C7 | 0.0219 (9) | 0.0232 (9) | 0.0264 (9) | 0.0016 (7) | −0.0007 (7) | −0.0004 (7) |
C6 | 0.0228 (9) | 0.0256 (9) | 0.0315 (10) | 0.0006 (7) | −0.0016 (8) | 0.0027 (8) |
O3—C2 | 1.419 (2) | C3—C4 | 1.528 (2) |
O3—H3 | 0.76 (3) | C2—H2 | 0.9800 |
O6—C4 | 1.283 (2) | C2—C1 | 1.521 (2) |
O6—H6 | 1.2317 (11) | N1—H1A | 0.8900 |
O4—H4 | 0.8200 | N1—H1B | 0.8900 |
O4—C3 | 1.4178 (19) | N1—H1C | 0.8900 |
O1—H1 | 0.8200 | N1—C7 | 1.483 (2) |
O1—C1 | 1.312 (2) | O7—C5 | 1.232 (2) |
O5—C4 | 1.224 (2) | C5—C6 | 1.512 (2) |
O8—C5 | 1.271 (2) | C7—H7A | 0.9700 |
O8—H8 | 1.2249 (12) | C7—H7B | 0.9700 |
O2—C1 | 1.204 (2) | C7—C6 | 1.505 (2) |
C3—H3A | 0.9800 | C6—H6A | 0.9700 |
C3—C2 | 1.530 (2) | C6—H6B | 0.9700 |
C2—O3—H3 | 115 (3) | C7—N1—H1C | 109.5 |
C4—O6—H6 | 114.32 (12) | O8—C5—C6 | 114.91 (16) |
C3—O4—H4 | 109.5 | O7—C5—O8 | 125.87 (17) |
C1—O1—H1 | 109.5 | O7—C5—C6 | 119.21 (17) |
C5—O8—H8 | 116.71 (13) | O1—C1—C2 | 111.95 (14) |
O4—C3—H3A | 109.1 | O2—C1—O1 | 125.10 (15) |
O4—C3—C2 | 110.97 (13) | O2—C1—C2 | 122.94 (16) |
O4—C3—C4 | 109.37 (13) | O6—C4—C3 | 113.48 (14) |
C2—C3—H3A | 109.1 | O5—C4—O6 | 125.53 (15) |
C4—C3—H3A | 109.1 | O5—C4—C3 | 120.98 (15) |
C4—C3—C2 | 109.30 (13) | N1—C7—H7A | 109.6 |
O3—C2—C3 | 111.15 (13) | N1—C7—H7B | 109.6 |
O3—C2—H2 | 108.4 | N1—C7—C6 | 110.22 (15) |
O3—C2—C1 | 109.77 (13) | H7A—C7—H7B | 108.1 |
C3—C2—H2 | 108.4 | C6—C7—H7A | 109.6 |
C1—C2—C3 | 110.57 (13) | C6—C7—H7B | 109.6 |
C1—C2—H2 | 108.4 | C5—C6—H6A | 108.9 |
H1A—N1—H1B | 109.5 | C5—C6—H6B | 108.9 |
H1A—N1—H1C | 109.5 | C7—C6—C5 | 113.50 (15) |
H1B—N1—H1C | 109.5 | C7—C6—H6A | 108.9 |
C7—N1—H1A | 109.5 | C7—C6—H6B | 108.9 |
C7—N1—H1B | 109.5 | H6A—C6—H6B | 107.7 |
O3—C2—C1—O1 | −178.92 (14) | C3—C2—C1—O2 | 122.88 (19) |
O3—C2—C1—O2 | −0.1 (2) | C2—C3—C4—O6 | −58.10 (18) |
O4—C3—C2—O3 | 67.20 (16) | C2—C3—C4—O5 | 121.42 (17) |
O4—C3—C2—C1 | −54.98 (18) | N1—C7—C6—C5 | 176.51 (15) |
O4—C3—C4—O6 | −179.77 (14) | O7—C5—C6—C7 | 143.16 (19) |
O4—C3—C4—O5 | −0.2 (2) | C4—C3—C2—O3 | −53.49 (17) |
O8—C5—C6—C7 | −38.2 (2) | C4—C3—C2—C1 | −175.68 (13) |
C3—C2—C1—O1 | −55.93 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3i | 0.82 | 1.97 | 2.7653 (17) | 165 |
O1—H1···O7ii | 0.82 | 1.79 | 2.6092 (18) | 174 |
N1—H1A···O4iii | 0.89 | 2.56 | 3.142 (2) | 124 |
N1—H1A···O5iii | 0.89 | 2.16 | 3.017 (2) | 161 |
N1—H1B···O5iv | 0.89 | 2.08 | 2.916 (2) | 155 |
N1—H1B···O2v | 0.89 | 2.52 | 3.064 (2) | 121 |
N1—H1C···O2vi | 0.89 | 2.37 | 2.986 (2) | 127 |
O6—H6···O6iv | 1.23 | 1.23 | 2.464 (2) | 180 |
O8—H8···O8vii | 1.22 | 1.22 | 2.4498 (19) | 180 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+2, −z+1; (iii) −x+1, −y+1, −z; (iv) −x, −y+1, −z; (v) x−1, y−1, z; (vi) x, y−1, z; (vii) −x+1, −y+2, −z+1. |
C4H10NO2+·C4H5O6− | Z = 4 |
Mr = 253.21 | F(000) = 536 |
Triclinic, P1 | Dx = 1.531 Mg m−3 |
a = 9.5645 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.6521 (7) Å | Cell parameters from 3135 reflections |
c = 14.3793 (8) Å | θ = 2.5–27.9° |
α = 100.043 (6)° | µ = 0.14 mm−1 |
β = 99.159 (6)° | T = 293 K |
γ = 118.841 (8)° | Block, colourless |
V = 1098.50 (16) Å3 | 0.50 × 0.19 × 0.04 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 4471 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3662 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 2.5° |
ω scans | h = −11→10 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→12 |
Tmin = 0.837, Tmax = 1.000 | l = −16→17 |
7048 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0573P)2 + 0.3075P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4471 reflections | Δρmax = 0.34 e Å−3 |
317 parameters | Δρmin = −0.43 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 | ||
O27 | 0.2335 (2) | 0.3689 (2) | 0.92438 (10) | 0.0559 (5) | |
H27 | 0.234925 | 0.453119 | 0.948700 | 0.067* | |
O28 | 0.3116 (3) | 0.2105 (2) | 0.97021 (11) | 0.0611 (5) | |
N21 | 0.15229 (19) | 0.48352 (18) | 1.29836 (11) | 0.0315 (3) | |
H21A | 0.081446 | 0.505581 | 1.266198 | 0.047* | |
H21B | 0.201127 | 0.551880 | 1.359302 | 0.047* | |
H21C | 0.097334 | 0.379626 | 1.300724 | 0.047* | |
C25 | 0.2971 (2) | 0.3285 (2) | 0.99280 (13) | 0.0333 (4) | |
C26 | 0.3525 (2) | 0.4299 (2) | 1.09787 (13) | 0.0343 (4) | |
H26A | 0.416804 | 0.546062 | 1.101709 | 0.041* | |
H26B | 0.424871 | 0.404818 | 1.137152 | 0.041* | |
C27 | 0.2082 (2) | 0.3992 (2) | 1.14145 (12) | 0.0287 (4) | |
H27A | 0.136324 | 0.426941 | 1.104287 | 0.034* | |
H27B | 0.142897 | 0.283547 | 1.138669 | 0.034* | |
C28 | 0.2799 (2) | 0.5059 (2) | 1.24674 (13) | 0.0331 (4) | |
H28A | 0.355721 | 0.480358 | 1.281845 | 0.040* | |
H28B | 0.343526 | 0.620878 | 1.247988 | 0.040* | |
O17 | 0.2916 (2) | 0.78703 (18) | 0.89978 (11) | 0.0528 (4) | |
H17 | 0.288267 | 0.707847 | 0.865098 | 0.063* | |
O18 | 0.2343 (3) | 0.63217 (19) | 1.00016 (12) | 0.0670 (6) | |
N11 | 0.18466 (18) | 0.96254 (17) | 1.30101 (11) | 0.0300 (3) | |
H11A | 0.099736 | 0.860186 | 1.290229 | 0.045* | |
H11B | 0.161938 | 1.034584 | 1.331430 | 0.045* | |
H11C | 0.276063 | 0.975514 | 1.338566 | 0.045* | |
C15 | 0.2619 (2) | 0.7581 (2) | 0.98005 (13) | 0.0322 (4) | |
C16 | 0.2598 (3) | 0.8926 (2) | 1.04874 (14) | 0.0396 (5) | |
H16A | 0.172193 | 0.906233 | 1.016206 | 0.048* | |
H16B | 0.364693 | 0.995464 | 1.061857 | 0.048* | |
C17 | 0.2329 (2) | 0.8619 (2) | 1.14583 (13) | 0.0322 (4) | |
H17A | 0.134656 | 0.753652 | 1.133485 | 0.039* | |
H17B | 0.327482 | 0.862586 | 1.182886 | 0.039* | |
C18 | 0.2117 (3) | 0.9914 (2) | 1.20568 (14) | 0.0347 (4) | |
H18A | 0.310174 | 1.099484 | 1.217999 | 0.042* | |
H18B | 0.117522 | 0.990906 | 1.168334 | 0.042* | |
O21 | 0.45891 (15) | 0.33231 (15) | 0.54409 (9) | 0.0289 (3) | |
H21 | 0.469131 | 0.270225 | 0.502773 | 0.035* | |
O22 | 0.24110 (16) | 0.26931 (16) | 0.42271 (9) | 0.0343 (3) | |
O23 | 0.17396 (15) | 0.46887 (14) | 0.53599 (9) | 0.0277 (3) | |
H23 | 0.101937 | 0.386506 | 0.491266 | 0.033* | |
O24 | 0.08990 (14) | 0.18626 (13) | 0.61368 (9) | 0.0278 (3) | |
H24 | 0.118448 | 0.120257 | 0.597192 | 0.033* | |
O25 | 0.05168 (15) | 0.38627 (15) | 0.74327 (9) | 0.0305 (3) | |
O26 | 0.31479 (15) | 0.59350 (14) | 0.77576 (9) | 0.0313 (3) | |
C21 | 0.3294 (2) | 0.33719 (19) | 0.50715 (12) | 0.0215 (3) | |
C22 | 0.2927 (2) | 0.43689 (19) | 0.58254 (12) | 0.0211 (3) | |
H22 | 0.396102 | 0.542966 | 0.616712 | 0.025* | |
C23 | 0.23280 (19) | 0.34588 (19) | 0.65918 (12) | 0.0218 (3) | |
H23A | 0.321942 | 0.335473 | 0.694751 | 0.026* | |
C24 | 0.1933 (2) | 0.4480 (2) | 0.73227 (11) | 0.0224 (3) | |
O11 | 0.67246 (17) | −0.09112 (15) | 0.20349 (10) | 0.0416 (4) | |
H11 | 0.693006 | −0.127099 | 0.154893 | 0.050* | |
O12 | 0.93554 (16) | 0.11821 (16) | 0.24006 (10) | 0.0373 (3) | |
O13 | 0.89270 (14) | 0.30379 (13) | 0.37845 (9) | 0.0265 (3) | |
H13 | 0.863097 | 0.367061 | 0.399222 | 0.032* | |
O14 | 0.80716 (15) | 0.02295 (15) | 0.45153 (9) | 0.0296 (3) | |
H14 | 0.869032 | 0.102185 | 0.500402 | 0.035* | |
O15 | 0.71741 (16) | 0.20586 (15) | 0.55839 (9) | 0.0335 (3) | |
O16 | 0.51851 (14) | 0.15786 (14) | 0.42978 (9) | 0.0287 (3) | |
C11 | 0.7995 (2) | 0.0580 (2) | 0.25300 (12) | 0.0259 (4) | |
C12 | 0.75111 (19) | 0.14582 (19) | 0.32773 (12) | 0.0224 (3) | |
H12 | 0.663850 | 0.159266 | 0.292717 | 0.027* | |
C13 | 0.6861 (2) | 0.04870 (19) | 0.40067 (12) | 0.0218 (3) | |
H13A | 0.586340 | −0.058992 | 0.364098 | 0.026* | |
C14 | 0.6386 (2) | 0.14525 (19) | 0.47132 (12) | 0.0219 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O27 | 0.1109 (14) | 0.0599 (10) | 0.0257 (7) | 0.0668 (10) | 0.0182 (8) | 0.0108 (7) |
O28 | 0.1201 (15) | 0.0574 (10) | 0.0379 (8) | 0.0673 (11) | 0.0296 (9) | 0.0155 (7) |
N21 | 0.0350 (8) | 0.0316 (8) | 0.0281 (8) | 0.0166 (7) | 0.0165 (7) | 0.0050 (6) |
C25 | 0.0484 (11) | 0.0333 (10) | 0.0278 (9) | 0.0250 (9) | 0.0198 (9) | 0.0115 (8) |
C26 | 0.0341 (10) | 0.0454 (11) | 0.0249 (9) | 0.0226 (9) | 0.0115 (8) | 0.0051 (8) |
C27 | 0.0299 (9) | 0.0312 (9) | 0.0236 (9) | 0.0154 (8) | 0.0095 (7) | 0.0054 (7) |
C28 | 0.0267 (9) | 0.0421 (11) | 0.0254 (9) | 0.0155 (8) | 0.0113 (8) | 0.0024 (8) |
O17 | 0.1020 (13) | 0.0450 (9) | 0.0354 (8) | 0.0490 (9) | 0.0381 (9) | 0.0166 (7) |
O18 | 0.1423 (17) | 0.0533 (10) | 0.0511 (10) | 0.0712 (11) | 0.0570 (11) | 0.0296 (8) |
N11 | 0.0324 (8) | 0.0296 (8) | 0.0272 (8) | 0.0159 (7) | 0.0131 (6) | 0.0032 (6) |
C15 | 0.0437 (11) | 0.0312 (9) | 0.0297 (10) | 0.0236 (9) | 0.0165 (8) | 0.0092 (8) |
C16 | 0.0651 (14) | 0.0327 (10) | 0.0344 (11) | 0.0313 (10) | 0.0267 (10) | 0.0115 (8) |
C17 | 0.0448 (11) | 0.0334 (10) | 0.0285 (9) | 0.0259 (9) | 0.0170 (8) | 0.0091 (8) |
C18 | 0.0498 (12) | 0.0331 (10) | 0.0312 (10) | 0.0264 (9) | 0.0205 (9) | 0.0094 (8) |
O21 | 0.0315 (7) | 0.0365 (7) | 0.0247 (6) | 0.0249 (6) | 0.0074 (5) | 0.0008 (5) |
O22 | 0.0416 (7) | 0.0415 (7) | 0.0228 (6) | 0.0291 (6) | 0.0034 (6) | −0.0012 (5) |
O23 | 0.0343 (7) | 0.0292 (6) | 0.0258 (6) | 0.0238 (6) | 0.0051 (5) | 0.0035 (5) |
O24 | 0.0285 (6) | 0.0223 (6) | 0.0350 (7) | 0.0161 (5) | 0.0118 (5) | 0.0029 (5) |
O25 | 0.0305 (7) | 0.0343 (7) | 0.0317 (7) | 0.0202 (6) | 0.0141 (5) | 0.0061 (5) |
O26 | 0.0325 (7) | 0.0288 (7) | 0.0254 (6) | 0.0130 (6) | 0.0097 (5) | −0.0007 (5) |
C21 | 0.0243 (8) | 0.0206 (8) | 0.0212 (8) | 0.0128 (7) | 0.0088 (7) | 0.0047 (6) |
C22 | 0.0242 (8) | 0.0224 (8) | 0.0212 (8) | 0.0160 (7) | 0.0074 (7) | 0.0036 (6) |
C23 | 0.0223 (8) | 0.0243 (8) | 0.0219 (8) | 0.0155 (7) | 0.0059 (7) | 0.0042 (6) |
C24 | 0.0295 (9) | 0.0293 (9) | 0.0153 (7) | 0.0199 (7) | 0.0084 (7) | 0.0068 (6) |
O11 | 0.0441 (8) | 0.0315 (7) | 0.0363 (8) | 0.0132 (6) | 0.0189 (6) | −0.0057 (6) |
O12 | 0.0338 (7) | 0.0406 (7) | 0.0393 (8) | 0.0210 (6) | 0.0189 (6) | 0.0030 (6) |
O13 | 0.0267 (6) | 0.0206 (6) | 0.0334 (7) | 0.0141 (5) | 0.0121 (5) | 0.0022 (5) |
O14 | 0.0351 (7) | 0.0299 (6) | 0.0301 (7) | 0.0244 (6) | 0.0052 (5) | 0.0041 (5) |
O15 | 0.0446 (8) | 0.0368 (7) | 0.0233 (7) | 0.0273 (6) | 0.0064 (6) | 0.0031 (5) |
O16 | 0.0266 (6) | 0.0349 (7) | 0.0295 (7) | 0.0214 (6) | 0.0088 (5) | 0.0031 (5) |
C11 | 0.0316 (9) | 0.0275 (9) | 0.0219 (8) | 0.0184 (8) | 0.0091 (7) | 0.0047 (7) |
C12 | 0.0228 (8) | 0.0239 (8) | 0.0230 (8) | 0.0148 (7) | 0.0077 (7) | 0.0034 (6) |
C13 | 0.0227 (8) | 0.0203 (8) | 0.0251 (8) | 0.0137 (7) | 0.0079 (7) | 0.0043 (6) |
C14 | 0.0241 (8) | 0.0198 (8) | 0.0256 (9) | 0.0125 (7) | 0.0127 (7) | 0.0073 (6) |
O27—H27 | 0.8200 | C18—H18A | 0.9700 |
O27—C25 | 1.289 (2) | C18—H18B | 0.9700 |
O28—C25 | 1.209 (2) | O21—H21 | 0.8200 |
N21—H21A | 0.8900 | O21—C21 | 1.2943 (19) |
N21—H21B | 0.8900 | O22—C21 | 1.216 (2) |
N21—H21C | 0.8900 | O23—H23 | 0.8200 |
N21—C28 | 1.475 (2) | O23—C22 | 1.4151 (18) |
C25—C26 | 1.500 (2) | O24—H24 | 0.8200 |
C26—H26A | 0.9700 | O24—C23 | 1.4149 (19) |
C26—H26B | 0.9700 | O25—C24 | 1.240 (2) |
C26—C27 | 1.527 (2) | O26—C24 | 1.265 (2) |
C27—H27A | 0.9700 | C21—C22 | 1.519 (2) |
C27—H27B | 0.9700 | C22—H22 | 0.9800 |
C27—C28 | 1.506 (2) | C22—C23 | 1.539 (2) |
C28—H28A | 0.9700 | C23—H23A | 0.9800 |
C28—H28B | 0.9700 | C23—C24 | 1.531 (2) |
O17—H17 | 0.8200 | O11—H11 | 0.8200 |
O17—C15 | 1.277 (2) | O11—C11 | 1.317 (2) |
O18—C15 | 1.211 (2) | O12—C11 | 1.204 (2) |
N11—H11A | 0.8900 | O13—H13 | 0.8200 |
N11—H11B | 0.8900 | O13—C12 | 1.4130 (19) |
N11—H11C | 0.8900 | O14—H14 | 0.8200 |
N11—C18 | 1.483 (2) | O14—C13 | 1.4171 (19) |
C15—C16 | 1.499 (2) | O15—C14 | 1.223 (2) |
C16—H16A | 0.9700 | O16—C14 | 1.278 (2) |
C16—H16B | 0.9700 | C11—C12 | 1.519 (2) |
C16—C17 | 1.513 (3) | C12—H12 | 0.9800 |
C17—H17A | 0.9700 | C12—C13 | 1.534 (2) |
C17—H17B | 0.9700 | C13—H13A | 0.9800 |
C17—C18 | 1.507 (2) | C13—C14 | 1.527 (2) |
C25—O27—H27 | 109.5 | C18—C17—H17B | 109.4 |
H21A—N21—H21B | 109.5 | N11—C18—C17 | 111.94 (15) |
H21A—N21—H21C | 109.5 | N11—C18—H18A | 109.2 |
H21B—N21—H21C | 109.5 | N11—C18—H18B | 109.2 |
C28—N21—H21A | 109.5 | C17—C18—H18A | 109.2 |
C28—N21—H21B | 109.5 | C17—C18—H18B | 109.2 |
C28—N21—H21C | 109.5 | H18A—C18—H18B | 107.9 |
O27—C25—C26 | 119.29 (16) | C21—O21—H21 | 109.5 |
O28—C25—O27 | 118.87 (17) | C22—O23—H23 | 109.5 |
O28—C25—C26 | 121.83 (18) | C23—O24—H24 | 109.5 |
C25—C26—H26A | 108.9 | O21—C21—C22 | 112.46 (13) |
C25—C26—H26B | 108.9 | O22—C21—O21 | 126.04 (15) |
C25—C26—C27 | 113.19 (15) | O22—C21—C22 | 121.49 (14) |
H26A—C26—H26B | 107.8 | O23—C22—C21 | 110.75 (13) |
C27—C26—H26A | 108.9 | O23—C22—H22 | 108.3 |
C27—C26—H26B | 108.9 | O23—C22—C23 | 110.91 (13) |
C26—C27—H27A | 110.1 | C21—C22—H22 | 108.3 |
C26—C27—H27B | 110.1 | C21—C22—C23 | 110.27 (12) |
H27A—C27—H27B | 108.4 | C23—C22—H22 | 108.3 |
C28—C27—C26 | 108.01 (14) | O24—C23—C22 | 111.18 (13) |
C28—C27—H27A | 110.1 | O24—C23—H23A | 109.0 |
C28—C27—H27B | 110.1 | O24—C23—C24 | 109.88 (13) |
N21—C28—C27 | 113.32 (14) | C22—C23—H23A | 109.0 |
N21—C28—H28A | 108.9 | C24—C23—C22 | 108.69 (12) |
N21—C28—H28B | 108.9 | C24—C23—H23A | 109.0 |
C27—C28—H28A | 108.9 | O25—C24—O26 | 126.30 (15) |
C27—C28—H28B | 108.9 | O25—C24—C23 | 119.82 (15) |
H28A—C28—H28B | 107.7 | O26—C24—C23 | 113.87 (14) |
C15—O17—H17 | 109.5 | C11—O11—H11 | 109.5 |
H11A—N11—H11B | 109.5 | C12—O13—H13 | 109.5 |
H11A—N11—H11C | 109.5 | C13—O14—H14 | 109.5 |
H11B—N11—H11C | 109.5 | O11—C11—C12 | 110.99 (14) |
C18—N11—H11A | 109.5 | O12—C11—O11 | 124.74 (15) |
C18—N11—H11B | 109.5 | O12—C11—C12 | 124.27 (15) |
C18—N11—H11C | 109.5 | O13—C12—C11 | 108.03 (13) |
O17—C15—C16 | 114.47 (16) | O13—C12—H12 | 108.9 |
O18—C15—O17 | 124.07 (17) | O13—C12—C13 | 110.25 (13) |
O18—C15—C16 | 121.44 (17) | C11—C12—H12 | 108.9 |
C15—C16—H16A | 108.7 | C11—C12—C13 | 111.91 (13) |
C15—C16—H16B | 108.7 | C13—C12—H12 | 108.9 |
C15—C16—C17 | 114.38 (15) | O14—C13—C12 | 110.84 (13) |
H16A—C16—H16B | 107.6 | O14—C13—H13A | 108.8 |
C17—C16—H16A | 108.7 | O14—C13—C14 | 111.66 (13) |
C17—C16—H16B | 108.7 | C12—C13—H13A | 108.8 |
C16—C17—H17A | 109.4 | C14—C13—C12 | 107.91 (12) |
C16—C17—H17B | 109.4 | C14—C13—H13A | 108.8 |
H17A—C17—H17B | 108.0 | O15—C14—O16 | 126.40 (15) |
C18—C17—C16 | 111.31 (15) | O15—C14—C13 | 119.69 (14) |
C18—C17—H17A | 109.4 | O16—C14—C13 | 113.87 (14) |
O27—C25—C26—C27 | 75.0 (2) | C21—C22—C23—O24 | −57.58 (16) |
O28—C25—C26—C27 | −105.7 (2) | C21—C22—C23—C24 | −178.66 (12) |
C25—C26—C27—C28 | 179.31 (16) | C22—C23—C24—O25 | 121.65 (16) |
C26—C27—C28—N21 | −178.20 (15) | C22—C23—C24—O26 | −57.62 (17) |
O17—C15—C16—C17 | −177.19 (18) | O11—C11—C12—O13 | 179.60 (14) |
O18—C15—C16—C17 | 4.1 (3) | O11—C11—C12—C13 | 58.04 (19) |
C15—C16—C17—C18 | −173.17 (18) | O12—C11—C12—O13 | −1.4 (2) |
C16—C17—C18—N11 | 179.80 (16) | O12—C11—C12—C13 | −122.93 (18) |
O21—C21—C22—O23 | 167.67 (13) | O13—C12—C13—O14 | −61.98 (16) |
O21—C21—C22—C23 | −69.19 (17) | O13—C12—C13—C14 | 60.57 (16) |
O22—C21—C22—O23 | −13.6 (2) | O14—C13—C14—O15 | 8.4 (2) |
O22—C21—C22—C23 | 109.58 (17) | O14—C13—C14—O16 | −173.69 (13) |
O23—C22—C23—O24 | 65.47 (16) | C11—C12—C13—O14 | 58.29 (17) |
O23—C22—C23—C24 | −55.61 (16) | C11—C12—C13—C14 | −179.16 (13) |
O24—C23—C24—O25 | −0.2 (2) | C12—C13—C14—O15 | −113.65 (16) |
O24—C23—C24—O26 | −179.49 (13) | C12—C13—C14—O16 | 64.26 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O27—H27···O18 | 0.82 | 1.76 | 2.5805 (19) | 179 |
N21—H21A···O25i | 0.89 | 2.00 | 2.828 (2) | 154 |
N21—H21B···O15ii | 0.89 | 2.11 | 2.8651 (19) | 142 |
N21—H21C···O12iii | 0.89 | 2.13 | 2.966 (2) | 155 |
O17—H17···O26 | 0.82 | 1.68 | 2.4663 (17) | 161 |
N11—H11A···O25i | 0.89 | 2.01 | 2.8813 (19) | 166 |
N11—H11B···O22iv | 0.89 | 2.10 | 2.9105 (19) | 151 |
N11—H11C···O15ii | 0.89 | 2.50 | 3.1013 (19) | 126 |
N11—H11C···O16iv | 0.89 | 2.12 | 2.8760 (19) | 143 |
O21—H21···O16 | 0.82 | 1.66 | 2.4740 (16) | 172 |
O23—H23···O13v | 0.82 | 2.06 | 2.7519 (17) | 142 |
O24—H24···O14vi | 0.82 | 1.92 | 2.7346 (16) | 174 |
O11—H11···O28vi | 0.82 | 1.82 | 2.6220 (19) | 165 |
O13—H13···O23vii | 0.82 | 1.91 | 2.7190 (15) | 171 |
O14—H14···O24viii | 0.82 | 2.14 | 2.7986 (17) | 138 |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+1, −z+2; (iii) x−1, y, z+1; (iv) x, y+1, z+1; (v) x−1, y, z; (vi) −x+1, −y, −z+1; (vii) −x+1, −y+1, −z+1; (viii) x+1, y, z. |
C8H19N2O4+·C8H11O12− | Z = 1 |
Mr = 506.42 | F(000) = 268 |
Triclinic, P1 | Dx = 1.577 Mg m−3 |
a = 4.9336 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.0324 (7) Å | Cell parameters from 3350 reflections |
c = 11.3232 (7) Å | θ = 1.9–28.0° |
α = 103.464 (6)° | µ = 0.14 mm−1 |
β = 94.310 (5)° | T = 293 K |
γ = 99.766 (5)° | Block, colourless |
V = 533.29 (6) Å3 | 0.35 × 0.06 × 0.05 mm |
Agilent Xcalibur Ruby Gemini ultra diffractometer | 2175 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1874 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.9° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −12→12 |
Tmin = 0.976, Tmax = 1.000 | l = −14→14 |
6684 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0403P)2 + 0.1383P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2175 reflections | Δρmax = 0.25 e Å−3 |
191 parameters | Δρmin = −0.18 e Å−3 |
23 restraints |
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 | Occ. (<1) | |
O4 | 0.75632 (19) | 0.32598 (10) | 1.01072 (9) | 0.0255 (2) | |
H4 | 0.897682 | 0.338873 | 0.977863 | 0.031* | |
O8 | 1.3362 (2) | 0.40774 (11) | 0.42712 (9) | 0.0280 (2) | |
O3 | 0.2374 (2) | 0.37769 (11) | 0.90602 (10) | 0.0297 (3) | |
H3 | 0.315593 | 0.458190 | 0.911471 | 0.036* | |
O5 | 0.4124 (2) | 0.17297 (12) | 1.11607 (9) | 0.0334 (3) | |
O2 | 0.6681 (2) | 0.48190 (11) | 0.79870 (10) | 0.0346 (3) | |
O7 | 1.0746 (2) | 0.37688 (12) | 0.57402 (9) | 0.0336 (3) | |
O6 | 0.1444 (2) | 0.06657 (11) | 0.94098 (9) | 0.0338 (3) | |
O1 | 0.6739 (2) | 0.26841 (11) | 0.68302 (10) | 0.0356 (3) | |
H1 | 0.789165 | 0.311031 | 0.649796 | 0.043* | |
N1 | 0.9600 (3) | 0.28541 (15) | 0.24398 (12) | 0.0282 (4) | 0.929 (2) |
H1A | 0.807242 | 0.258948 | 0.190655 | 0.042* | 0.929 (2) |
H1B | 1.082913 | 0.232909 | 0.218571 | 0.042* | 0.929 (2) |
H1C | 1.031632 | 0.374641 | 0.249848 | 0.042* | 0.929 (2) |
C5 | 1.1146 (3) | 0.35785 (14) | 0.46582 (12) | 0.0212 (3) | |
C3 | 0.5533 (3) | 0.22179 (14) | 0.92920 (12) | 0.0202 (3) | |
H3A | 0.645756 | 0.152254 | 0.881010 | 0.024* | |
C2 | 0.3900 (3) | 0.28414 (14) | 0.84129 (12) | 0.0210 (3) | |
H2 | 0.260983 | 0.208003 | 0.783101 | 0.025* | |
C4 | 0.3585 (3) | 0.15024 (14) | 1.00450 (12) | 0.0213 (3) | |
C1 | 0.5908 (3) | 0.35722 (15) | 0.77114 (12) | 0.0229 (3) | |
C6 | 0.8900 (3) | 0.26824 (14) | 0.36602 (12) | 0.0222 (3) | |
H6A | 0.715811 | 0.300498 | 0.380465 | 0.027* | |
C7 | 0.8473 (3) | 0.11414 (16) | 0.36772 (15) | 0.0268 (4) | 0.929 (2) |
H7A | 0.762672 | 0.102602 | 0.440209 | 0.032* | 0.929 (2) |
H7B | 0.719585 | 0.059729 | 0.296961 | 0.032* | 0.929 (2) |
C8 | 1.1142 (5) | 0.0565 (2) | 0.3669 (2) | 0.0375 (5) | 0.929 (2) |
H8A | 1.197986 | 0.065941 | 0.294702 | 0.056* | 0.929 (2) |
H8B | 1.072898 | −0.040321 | 0.367434 | 0.056* | 0.929 (2) |
H8C | 1.239846 | 0.107750 | 0.438085 | 0.056* | 0.929 (2) |
N1A | 0.836 (3) | 0.3589 (18) | 0.2746 (14) | 0.0219 (19) | 0.071 (2) |
H1AA | 0.698469 | 0.311535 | 0.216960 | 0.033* | 0.071 (2) |
H1AB | 0.988911 | 0.379034 | 0.239957 | 0.033* | 0.071 (2) |
H1AC | 0.790358 | 0.437759 | 0.314762 | 0.033* | 0.071 (2) |
C8A | 1.006 (6) | 0.066 (3) | 0.376 (2) | 0.025 (2) | 0.071 (2) |
H8AA | 1.113371 | 0.121108 | 0.450788 | 0.038* | 0.071 (2) |
H8AB | 1.100309 | −0.005838 | 0.338088 | 0.038* | 0.071 (2) |
H8AC | 0.827912 | 0.024295 | 0.392840 | 0.038* | 0.071 (2) |
C7A | 0.975 (4) | 0.141 (2) | 0.3067 (19) | 0.0248 (12) | 0.071 (2) |
H7AA | 0.836722 | 0.089739 | 0.238668 | 0.030* | 0.071 (2) |
H7AB | 1.148022 | 0.164339 | 0.274037 | 0.030* | 0.071 (2) |
H8 | 1.500000 | 0.500000 | 0.500000 | 0.087 (11)* | |
H6 | 0.000000 | 0.000000 | 1.000000 | 0.128 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0172 (5) | 0.0317 (6) | 0.0247 (5) | −0.0050 (4) | 0.0030 (4) | 0.0084 (4) |
O8 | 0.0209 (5) | 0.0341 (6) | 0.0230 (5) | −0.0046 (4) | 0.0042 (4) | 0.0023 (4) |
O3 | 0.0265 (5) | 0.0270 (5) | 0.0400 (6) | 0.0069 (4) | 0.0147 (5) | 0.0123 (5) |
O5 | 0.0285 (6) | 0.0457 (7) | 0.0241 (5) | −0.0075 (5) | 0.0017 (4) | 0.0159 (5) |
O2 | 0.0443 (7) | 0.0258 (6) | 0.0340 (6) | −0.0013 (5) | 0.0141 (5) | 0.0111 (5) |
O7 | 0.0312 (6) | 0.0435 (6) | 0.0219 (5) | −0.0018 (5) | 0.0079 (4) | 0.0048 (5) |
O6 | 0.0300 (6) | 0.0382 (6) | 0.0274 (6) | −0.0144 (5) | −0.0002 (4) | 0.0129 (5) |
O1 | 0.0430 (7) | 0.0322 (6) | 0.0336 (6) | 0.0039 (5) | 0.0212 (5) | 0.0090 (5) |
N1 | 0.0278 (7) | 0.0307 (8) | 0.0237 (7) | −0.0032 (6) | −0.0036 (5) | 0.0106 (6) |
C5 | 0.0204 (6) | 0.0211 (7) | 0.0221 (7) | 0.0041 (5) | 0.0036 (5) | 0.0051 (5) |
C3 | 0.0178 (6) | 0.0201 (7) | 0.0218 (7) | −0.0003 (5) | 0.0043 (5) | 0.0059 (5) |
C2 | 0.0200 (7) | 0.0213 (7) | 0.0210 (7) | 0.0000 (5) | 0.0042 (5) | 0.0062 (5) |
C4 | 0.0212 (7) | 0.0206 (7) | 0.0229 (7) | 0.0010 (5) | 0.0033 (5) | 0.0086 (5) |
C1 | 0.0233 (7) | 0.0273 (7) | 0.0195 (7) | 0.0029 (6) | 0.0031 (5) | 0.0098 (6) |
C6 | 0.0168 (6) | 0.0263 (7) | 0.0234 (7) | 0.0020 (5) | 0.0033 (5) | 0.0073 (6) |
C7 | 0.0267 (8) | 0.0241 (8) | 0.0279 (8) | −0.0016 (7) | 0.0023 (7) | 0.0078 (6) |
C8 | 0.0407 (12) | 0.0313 (10) | 0.0431 (11) | 0.0151 (10) | 0.0014 (10) | 0.0100 (8) |
N1A | 0.018 (4) | 0.027 (3) | 0.019 (4) | 0.001 (3) | 0.003 (3) | 0.004 (3) |
C8A | 0.018 (4) | 0.027 (4) | 0.027 (4) | 0.003 (4) | 0.001 (4) | 0.002 (4) |
C7A | 0.019 (2) | 0.028 (2) | 0.026 (2) | 0.0018 (19) | 0.003 (2) | 0.0044 (19) |
O4—H4 | 0.8200 | C2—H2 | 0.9800 |
O4—C3 | 1.4157 (16) | C2—C1 | 1.5142 (18) |
O8—C5 | 1.2750 (16) | C6—H6A | 0.9800 |
O8—H8 | 1.2170 (9) | C6—C7 | 1.529 (2) |
O3—H3 | 0.8200 | C6—N1A | 1.565 (16) |
O3—C2 | 1.4098 (16) | C6—C7A | 1.44 (2) |
O5—C4 | 1.2301 (16) | C7—H7A | 0.9700 |
O2—C1 | 1.2025 (17) | C7—H7B | 0.9700 |
O7—C5 | 1.2315 (16) | C7—C8 | 1.525 (3) |
O6—C4 | 1.2813 (16) | C8—H8A | 0.9600 |
O6—H6 | 1.2322 (9) | C8—H8B | 0.9600 |
O1—H1 | 0.8200 | C8—H8C | 0.9600 |
O1—C1 | 1.3148 (17) | N1A—H1AA | 0.8900 |
N1—H1A | 0.8900 | N1A—H1AB | 0.8900 |
N1—H1B | 0.8900 | N1A—H1AC | 0.8900 |
N1—H1C | 0.8900 | C8A—H8AA | 0.9600 |
N1—C6 | 1.4902 (18) | C8A—H8AB | 0.9600 |
C5—C6 | 1.5214 (18) | C8A—H8AC | 0.9600 |
C3—H3A | 0.9800 | C8A—C7A | 1.22 (4) |
C3—C2 | 1.5400 (18) | C7A—H7AA | 0.9700 |
C3—C4 | 1.5297 (17) | C7A—H7AB | 0.9700 |
C3—O4—H4 | 109.5 | C5—C6—C7 | 111.67 (11) |
C5—O8—H8 | 116.90 (10) | C5—C6—N1A | 106.9 (6) |
C2—O3—H3 | 109.5 | C7—C6—H6A | 108.2 |
C4—O6—H6 | 114.10 (10) | C7A—C6—C5 | 110.5 (8) |
C1—O1—H1 | 109.5 | C7A—C6—N1A | 112.0 (10) |
H1A—N1—H1B | 109.5 | C6—C7—H7A | 108.8 |
H1A—N1—H1C | 109.5 | C6—C7—H7B | 108.8 |
H1B—N1—H1C | 109.5 | H7A—C7—H7B | 107.7 |
C6—N1—H1A | 109.5 | C8—C7—C6 | 113.72 (14) |
C6—N1—H1B | 109.5 | C8—C7—H7A | 108.8 |
C6—N1—H1C | 109.5 | C8—C7—H7B | 108.8 |
O8—C5—C6 | 114.66 (11) | C7—C8—H8A | 109.5 |
O7—C5—O8 | 125.25 (13) | C7—C8—H8B | 109.5 |
O7—C5—C6 | 120.10 (12) | C7—C8—H8C | 109.5 |
O4—C3—H3A | 108.8 | H8A—C8—H8B | 109.5 |
O4—C3—C2 | 111.44 (11) | H8A—C8—H8C | 109.5 |
O4—C3—C4 | 108.41 (10) | H8B—C8—H8C | 109.5 |
C2—C3—H3A | 108.8 | C6—N1A—H1AA | 109.5 |
C4—C3—H3A | 108.8 | C6—N1A—H1AB | 109.5 |
C4—C3—C2 | 110.64 (11) | C6—N1A—H1AC | 109.5 |
O3—C2—C3 | 110.81 (11) | H1AA—N1A—H1AB | 109.5 |
O3—C2—H2 | 108.8 | H1AA—N1A—H1AC | 109.5 |
O3—C2—C1 | 110.71 (11) | H1AB—N1A—H1AC | 109.5 |
C3—C2—H2 | 108.8 | H8AA—C8A—H8AB | 109.5 |
C1—C2—C3 | 108.97 (11) | H8AA—C8A—H8AC | 109.5 |
C1—C2—H2 | 108.8 | H8AB—C8A—H8AC | 109.5 |
O5—C4—O6 | 124.93 (12) | C7A—C8A—H8AA | 109.5 |
O5—C4—C3 | 120.95 (12) | C7A—C8A—H8AB | 109.5 |
O6—C4—C3 | 114.12 (11) | C7A—C8A—H8AC | 109.5 |
O2—C1—O1 | 125.78 (13) | C6—C7A—H7AA | 109.0 |
O2—C1—C2 | 122.08 (13) | C6—C7A—H7AB | 109.0 |
O1—C1—C2 | 112.08 (12) | C8A—C7A—C6 | 113 (2) |
N1—C6—C5 | 110.10 (11) | C8A—C7A—H7AA | 109.0 |
N1—C6—H6A | 108.2 | C8A—C7A—H7AB | 109.0 |
N1—C6—C7 | 110.26 (12) | H7AA—C7A—H7AB | 107.8 |
C5—C6—H6A | 108.2 | ||
O4—C3—C2—O3 | −64.28 (13) | O7—C5—C6—N1A | 125.5 (7) |
O4—C3—C2—C1 | 57.77 (14) | O7—C5—C6—C7A | −112.4 (9) |
O4—C3—C4—O5 | −9.52 (18) | N1—C6—C7—C8 | 71.12 (17) |
O4—C3—C4—O6 | 171.22 (12) | C5—C6—C7—C8 | −51.63 (18) |
O8—C5—C6—N1 | −12.38 (17) | C5—C6—C7A—C8A | 64 (2) |
O8—C5—C6—C7 | 110.46 (14) | C3—C2—C1—O2 | −100.37 (15) |
O8—C5—C6—N1A | −54.6 (7) | C3—C2—C1—O1 | 77.04 (14) |
O8—C5—C6—C7A | 67.5 (9) | C2—C3—C4—O5 | −132.00 (14) |
O3—C2—C1—O2 | 21.74 (18) | C2—C3—C4—O6 | 48.74 (16) |
O3—C2—C1—O1 | −160.85 (12) | C4—C3—C2—O3 | 56.41 (14) |
O7—C5—C6—N1 | 167.80 (13) | C4—C3—C2—C1 | 178.47 (11) |
O7—C5—C6—C7 | −69.36 (17) | N1A—C6—C7A—C8A | −176.9 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3i | 0.82 | 1.94 | 2.7567 (13) | 177 |
O3—H3···O4ii | 0.82 | 2.24 | 2.8961 (14) | 138 |
O1—H1···O7 | 0.82 | 1.81 | 2.6228 (14) | 169 |
N1—H1A···O4iii | 0.89 | 2.30 | 2.8969 (16) | 125 |
N1—H1A···O5iii | 0.89 | 2.02 | 2.8785 (16) | 161 |
N1—H1B···O5iv | 0.89 | 2.15 | 2.9887 (19) | 156 |
N1—H1C···O2v | 0.89 | 2.08 | 2.8733 (16) | 148 |
N1A—H1AA···O5iii | 0.89 | 1.89 | 2.761 (16) | 165 |
N1A—H1AB···O2v | 0.89 | 2.14 | 2.970 (16) | 154 |
N1A—H1AC···O7v | 0.89 | 1.96 | 2.745 (17) | 146 |
C7A—H7AA···O6vi | 0.97 | 2.28 | 3.03 (2) | 133 |
O6—H6···O6vii | 1.23 | 1.23 | 2.4644 (19) | 180 |
O8—H8···O8viii | 1.22 | 1.22 | 2.4341 (19) | 180 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) x, y, z−1; (iv) x+1, y, z−1; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y, −z+1; (vii) −x, −y, −z+2; (viii) −x+3, −y+1, −z+1. |
Compound | Space group | V | Z, | Z' | V/Z |
(I) | P21/c | 900.3 | 4 | 1 | 225.1 |
(II) | P21/c | 976.7 | 4 | 1 | 244.2 |
(III) | P1 | 479.8 | 2 | 1 | 239.9 |
(IV) | P1 | 1098.5 | 4 | 2 | 274.6 |
(V) | P1 | 533.2 | 2 | 1 | 266.6 |
Compound | Polymorph | Refcode (reference) | Coordination number of the amino acid | n(DL-Tartaric acid)/n(amino acid) |
Glycine | α | GLYCIN28 (Drebushchak, Boldyreva, Seretkin et al., 2002) | 5 | n/a |
β | GLYCIN25 (Drebushchak, Boldyreva, Shutova et al., 2002) | 6 | n/a | |
γ | GLYCIN33 (Boldyreva et al., 2003) | 6 | n/a | |
Glycine–DL-tartaric acid, (I) | (Mohandas et al., 2013) | 6 (2 gly + 4 tart acid) | 2 | |
β-Alanine | BALNIN01 (Papavinasam et al., 1986) | 5 | n/a | |
β-Alanine–DL-tartaric acid, (II) | 5 (2 β-ala + 3 tart acid) | 3/2 | ||
β-Alanine-DL–tartaric acid, (III) | 4 (1 β-ala + 3 tart acid) | 3 | ||
GABA | Monoclinic | GAMBUT10 (Tomita et al., 1973) | 5 | n/a |
Tetragonal | GAMBUT04 (Dobson & Gerkin, 1996) | 6 | ||
GABA–DL-tartaric acid, (IV) | 5 (1 GABA + 4 tart acid) | 4 | ||
DL-AABA | Tetragonal | DLABUT12 (Voogd & Hulscher, 1980) | 5 | n/a |
Monoclinic (P21/c) | DLABUT13 (Görbitz et al., 2012) | 5 | n/a | |
Monoclinic (C2/c) | HUWSOI02 (Görbitz et al., 2012) | 6 | n/a | |
DL-AABA–DL-tartaric acid, (V) | 5 (1 DL-2-AABA + 4 tart acid) | 4 |
Compound | Melting (with decomposition) | End of the process |
Gly–DL-Tart, (I) | 434 | 439 |
β-Ala–DL-Tart, (II) | 428 | 433 |
β-Ala–DL-Tart, (III) | 413 | 420 |
GABA–DL-Tart, (IV) | 408 | 418 |
DL-AABA–DL-Tart, (V) | 429 | 431 |
Component | Melting point | |
Data from Dawson et al. (1986) | Data from Reaxys (Elsevier, 2017) | |
Glycine | 565 (decomp.) | 534 (decomp.) |
β-Alanine | 480 (decomp.) | 475 |
GABA | 476 (decomp.) | 474 |
DL-AABA | >573 (sublim.) | 556–558 (decomp.) |
DL-Tartaric acid | 479 | 486 |