Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011294/sj2241sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011294/sj2241Isup2.hkl |
CCDC reference: 643105
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.049
- wR factor = 0.130
- Data-to-parameter ratio = 6.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.54 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.93 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.38 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.22 PLAT301_ALERT_3_C Main Residue Disorder ......................... 1.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT731_ALERT_1_C Bond Calc 0.83(6), Rep 0.83(2) ...... 3.00 su-Ra O13 -H13A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(6), Rep 0.83(2) ...... 3.00 su-Ra O13 -H13A 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C6 H7 N2 O
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.97 From the CIF: _reflns_number_total 2732 Count of symmetry unique reflns 2750 Completeness (_total/calc) 99.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Version 1.4.1; Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL/PC.
2C6H7N2O+·2C4H5O6−·1.25H2O | F(000) = 593 |
Mr = 566.95 | Dx = 1.549 Mg m−3 Dm = 1.53 (1) Mg m−3 Dm measured by flotation using a mixture of xylene and carbon tetrachloride |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 7.654 (3) Å | θ = 9.8–13.9° |
b = 15.473 (9) Å | µ = 0.14 mm−1 |
c = 10.514 (6) Å | T = 293 K |
β = 102.489 (15)° | Needle, colourless |
V = 1215.7 (11) Å3 | 0.22 × 0.18 × 0.14 mm |
Z = 2 |
Nonius MACH3 sealed tube diffractometer | 1741 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 27.0°, θmin = 2.4° |
ω/2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→18 |
Tmin = 0.949, Tmax = 0.972 | l = −13→13 |
3208 measured reflections | 3 standard reflections every 60 min |
2732 independent reflections | intensity decay: none |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0712P)2] where P = (Fo2 + 2Fc2)/3 |
2732 reflections | (Δ/σ)max < 0.001 |
418 parameters | Δρmax = 0.30 e Å−3 |
7 restraints | Δρmin = −0.30 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C11 | 0.2045 (6) | 0.7836 (3) | 0.7039 (4) | 0.0298 (11) | |
C12 | 0.3848 (6) | 0.8020 (3) | 0.6678 (4) | 0.0281 (10) | |
H12 | 0.4594 | 0.8361 | 0.7376 | 0.034* | |
C13 | 0.4793 (6) | 0.7171 (3) | 0.6537 (4) | 0.0286 (10) | |
H13 | 0.5048 | 0.6880 | 0.7386 | 0.034* | |
C14 | 0.6563 (6) | 0.7325 (3) | 0.6132 (4) | 0.0302 (10) | |
O11 | 0.0631 (4) | 0.8117 (2) | 0.6274 (3) | 0.0403 (9) | |
O12 | 0.2062 (4) | 0.7419 (3) | 0.8044 (3) | 0.0405 (9) | |
O13 | 0.3617 (5) | 0.8491 (2) | 0.5488 (4) | 0.0387 (9) | |
O14 | 0.3665 (4) | 0.6625 (2) | 0.5630 (3) | 0.0329 (8) | |
O15 | 0.6943 (5) | 0.6961 (4) | 0.5232 (4) | 0.0714 (15) | |
O16 | 0.7575 (5) | 0.7886 (3) | 0.6869 (4) | 0.0426 (10) | |
H13A | 0.420 (10) | 0.895 (3) | 0.561 (8) | 0.11 (3)* | |
H14 | 0.332 (6) | 0.696 (3) | 0.488 (5) | 0.028 (13)* | |
H16 | 0.870 (10) | 0.792 (5) | 0.672 (6) | 0.08 (2)* | |
C21 | 0.2065 (6) | 0.7691 (3) | 0.2300 (4) | 0.0267 (10) | |
C22 | 0.3875 (5) | 0.7948 (3) | 0.2008 (4) | 0.0283 (10) | |
H22 | 0.4665 | 0.8147 | 0.2816 | 0.034* | |
C23 | 0.4694 (6) | 0.7150 (3) | 0.1526 (4) | 0.0317 (11) | |
H23 | 0.4949 | 0.6732 | 0.2243 | 0.038* | |
C24 | 0.6458 (6) | 0.7379 (3) | 0.1165 (4) | 0.0317 (11) | |
O21 | 0.0677 (4) | 0.8028 (3) | 0.1614 (4) | 0.0460 (10) | |
O22 | 0.2088 (4) | 0.7164 (2) | 0.3187 (3) | 0.0362 (9) | |
O23 | 0.3750 (5) | 0.8598 (3) | 0.1068 (4) | 0.0412 (9) | |
O24 | 0.3500 (5) | 0.6756 (2) | 0.0473 (3) | 0.0404 (9) | |
O25 | 0.6714 (5) | 0.7283 (3) | 0.0079 (3) | 0.0547 (11) | |
O26 | 0.7612 (5) | 0.7721 (3) | 0.2137 (3) | 0.0454 (11) | |
H23A | 0.344 (10) | 0.910 (5) | 0.116 (7) | 0.08 (3)* | |
H24 | 0.318 (8) | 0.711 (5) | −0.030 (7) | 0.07 (2)* | |
H26 | 0.868 (9) | 0.782 (5) | 0.194 (6) | 0.07 (2)* | |
N1A | −0.0020 (6) | 0.9198 (3) | 0.4270 (4) | 0.0378 (10) | |
C2A | 0.0963 (7) | 0.9613 (4) | 0.3581 (4) | 0.0367 (12) | |
H2A | 0.2189 | 0.9514 | 0.3736 | 0.044* | |
C3A | 0.0180 (6) | 1.0198 (3) | 0.2626 (5) | 0.0341 (11) | |
C4A | −0.1665 (7) | 1.0327 (3) | 0.2414 (5) | 0.0404 (13) | |
H4A | −0.2232 | 1.0712 | 0.1778 | 0.049* | |
C5A | −0.2632 (7) | 0.9879 (4) | 0.3156 (5) | 0.0451 (13) | |
H5A | −0.3861 | 0.9962 | 0.3026 | 0.054* | |
C6A | −0.1800 (7) | 0.9315 (4) | 0.4077 (5) | 0.0408 (13) | |
H6A | −0.2459 | 0.9010 | 0.4575 | 0.049* | |
C7A | 0.1398 (7) | 1.0622 (3) | 0.1865 (5) | 0.0347 (12) | |
N2A | 0.0831 (7) | 1.1354 (3) | 0.1257 (5) | 0.0435 (12) | |
O1A | 0.2826 (5) | 1.0270 (3) | 0.1808 (4) | 0.0509 (10) | |
H1A | 0.039 (7) | 0.883 (4) | 0.500 (5) | 0.036 (14)* | |
H2A1 | 0.159 (8) | 1.162 (4) | 0.076 (5) | 0.048 (16)* | |
H2A2 | −0.014 (8) | 1.170 (4) | 0.143 (5) | 0.045 (15)* | |
N1B | 0.0000 (6) | 0.9052 (3) | −0.0463 (4) | 0.0387 (11) | |
C2B | 0.0998 (7) | 0.9451 (3) | −0.1189 (5) | 0.0370 (12) | |
H2B | 0.2206 | 0.9315 | −0.1079 | 0.044* | |
C3B | 0.0245 (6) | 1.0059 (3) | −0.2092 (4) | 0.0317 (11) | |
C4B | −0.1564 (7) | 1.0234 (3) | −0.2239 (5) | 0.0402 (13) | |
H4B | −0.2115 | 1.0637 | −0.2852 | 0.048* | |
C5B | −0.2545 (8) | 0.9809 (4) | −0.1474 (6) | 0.0488 (14) | |
H5B | −0.3755 | 0.9930 | −0.1563 | 0.059* | |
C6B | −0.1743 (7) | 0.9217 (4) | −0.0599 (5) | 0.0444 (14) | |
H6B | −0.2404 | 0.8924 | −0.0090 | 0.053* | |
C7B | 0.1444 (7) | 1.0454 (3) | −0.2895 (5) | 0.0366 (12) | |
N2B | 0.0799 (7) | 1.1101 (3) | −0.3672 (5) | 0.0450 (12) | |
O1B | 0.2946 (5) | 1.0165 (3) | −0.2813 (4) | 0.0560 (11) | |
H1B | 0.042 (7) | 0.866 (4) | 0.012 (5) | 0.040 (15)* | |
H2B1 | 0.148 (11) | 1.131 (5) | −0.415 (8) | 0.10 (3)* | |
H2B2 | −0.027 (8) | 1.139 (3) | −0.361 (5) | 0.041 (15)* | |
O1W | 0.4982 (5) | 0.5120 (3) | 0.4615 (4) | 0.0518 (10) | |
H11W | 0.498 (10) | 0.563 (3) | 0.507 (5) | 0.078* | |
H12W | 0.546 (9) | 0.532 (4) | 0.395 (5) | 0.078* | |
O2W | 0.510 (4) | 0.5224 (16) | 0.968 (3) | 0.100 (7) | 0.25 |
H21W | 0.58 (4) | 0.542 (5) | 0.91 (3) | 0.151* | 0.25 |
H22W | 0.4635 | 0.5686 | 0.9932 | 0.151* | 0.25 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.019 (2) | 0.039 (3) | 0.034 (2) | −0.002 (2) | 0.0100 (19) | −0.005 (2) |
C12 | 0.023 (2) | 0.026 (2) | 0.036 (2) | −0.001 (2) | 0.0083 (19) | 0.000 (2) |
C13 | 0.020 (2) | 0.036 (3) | 0.030 (2) | −0.001 (2) | 0.0052 (18) | −0.003 (2) |
C14 | 0.025 (2) | 0.034 (3) | 0.034 (2) | 0.006 (2) | 0.0115 (19) | 0.002 (2) |
O11 | 0.0157 (17) | 0.061 (2) | 0.0459 (19) | 0.0019 (17) | 0.0101 (15) | 0.0106 (18) |
O12 | 0.0246 (19) | 0.062 (3) | 0.0377 (18) | 0.0036 (18) | 0.0117 (15) | 0.0076 (19) |
O13 | 0.031 (2) | 0.036 (2) | 0.052 (2) | −0.0012 (17) | 0.0167 (16) | 0.0072 (18) |
O14 | 0.0242 (18) | 0.033 (2) | 0.0407 (19) | −0.0043 (15) | 0.0060 (14) | −0.0013 (16) |
O15 | 0.045 (2) | 0.106 (4) | 0.074 (3) | −0.018 (3) | 0.036 (2) | −0.043 (3) |
O16 | 0.0214 (18) | 0.056 (2) | 0.054 (2) | −0.0091 (18) | 0.0168 (16) | −0.012 (2) |
C21 | 0.022 (2) | 0.030 (3) | 0.029 (2) | −0.001 (2) | 0.0082 (18) | −0.002 (2) |
C22 | 0.017 (2) | 0.033 (3) | 0.036 (2) | 0.000 (2) | 0.0076 (18) | 0.001 (2) |
C23 | 0.023 (2) | 0.039 (3) | 0.034 (2) | −0.003 (2) | 0.0101 (19) | 0.001 (2) |
C24 | 0.023 (2) | 0.036 (3) | 0.039 (2) | 0.002 (2) | 0.013 (2) | 0.003 (2) |
O21 | 0.0188 (19) | 0.066 (3) | 0.055 (2) | 0.0063 (19) | 0.0099 (15) | 0.023 (2) |
O22 | 0.0284 (19) | 0.049 (2) | 0.0320 (16) | −0.0043 (17) | 0.0093 (14) | 0.0038 (16) |
O23 | 0.032 (2) | 0.035 (2) | 0.062 (2) | 0.0055 (18) | 0.0205 (17) | 0.015 (2) |
O24 | 0.031 (2) | 0.044 (2) | 0.045 (2) | −0.0094 (17) | 0.0073 (16) | −0.0045 (19) |
O25 | 0.045 (2) | 0.076 (3) | 0.051 (2) | −0.008 (2) | 0.0271 (18) | −0.012 (2) |
O26 | 0.0153 (17) | 0.078 (3) | 0.045 (2) | −0.0058 (19) | 0.0123 (16) | −0.002 (2) |
N1A | 0.037 (3) | 0.041 (3) | 0.037 (2) | 0.003 (2) | 0.0111 (19) | 0.003 (2) |
C2A | 0.031 (3) | 0.044 (3) | 0.036 (3) | 0.000 (2) | 0.009 (2) | 0.002 (2) |
C3A | 0.028 (3) | 0.037 (3) | 0.039 (3) | −0.002 (2) | 0.011 (2) | −0.006 (2) |
C4A | 0.037 (3) | 0.037 (3) | 0.047 (3) | 0.006 (3) | 0.008 (2) | −0.001 (2) |
C5A | 0.031 (3) | 0.048 (3) | 0.059 (3) | 0.000 (3) | 0.017 (2) | −0.003 (3) |
C6A | 0.033 (3) | 0.044 (3) | 0.050 (3) | −0.005 (3) | 0.018 (2) | 0.000 (3) |
C7A | 0.031 (3) | 0.037 (3) | 0.038 (3) | −0.002 (2) | 0.010 (2) | −0.001 (2) |
N2A | 0.039 (3) | 0.041 (3) | 0.055 (3) | 0.008 (2) | 0.021 (2) | 0.015 (2) |
O1A | 0.036 (2) | 0.052 (2) | 0.070 (3) | 0.007 (2) | 0.0229 (19) | 0.012 (2) |
N1B | 0.043 (3) | 0.041 (3) | 0.032 (2) | 0.002 (2) | 0.006 (2) | 0.005 (2) |
C2B | 0.032 (3) | 0.044 (3) | 0.037 (2) | 0.008 (2) | 0.011 (2) | 0.001 (2) |
C3B | 0.026 (3) | 0.031 (3) | 0.038 (2) | −0.001 (2) | 0.007 (2) | −0.001 (2) |
C4B | 0.024 (3) | 0.039 (3) | 0.056 (3) | 0.004 (2) | 0.006 (2) | 0.014 (3) |
C5B | 0.032 (3) | 0.048 (4) | 0.068 (3) | −0.001 (3) | 0.014 (3) | 0.017 (3) |
C6B | 0.039 (3) | 0.046 (3) | 0.051 (3) | −0.001 (3) | 0.017 (3) | 0.005 (3) |
C7B | 0.033 (3) | 0.037 (3) | 0.044 (3) | 0.000 (2) | 0.020 (2) | −0.002 (2) |
N2B | 0.038 (3) | 0.045 (3) | 0.057 (3) | 0.007 (2) | 0.023 (2) | 0.010 (2) |
O1B | 0.034 (2) | 0.073 (3) | 0.068 (2) | 0.017 (2) | 0.0272 (19) | 0.021 (2) |
O1W | 0.051 (2) | 0.046 (2) | 0.067 (3) | 0.004 (2) | 0.031 (2) | −0.004 (2) |
O2W | 0.113 (18) | 0.070 (14) | 0.13 (2) | −0.001 (15) | 0.054 (16) | −0.007 (14) |
C11—O12 | 1.236 (5) | C2A—H2A | 0.9300 |
C11—O11 | 1.277 (6) | C3A—C4A | 1.395 (7) |
C11—C12 | 1.535 (6) | C3A—C7A | 1.505 (7) |
C12—O13 | 1.426 (6) | C4A—C5A | 1.374 (7) |
C12—C13 | 1.524 (6) | C4A—H4A | 0.9300 |
C12—H12 | 0.9800 | C5A—C6A | 1.355 (8) |
C13—O14 | 1.419 (5) | C5A—H5A | 0.9300 |
C13—C14 | 1.524 (6) | C6A—H6A | 0.9300 |
C13—H13 | 0.9800 | C7A—O1A | 1.234 (6) |
C14—O15 | 1.190 (6) | C7A—N2A | 1.326 (7) |
C14—O16 | 1.303 (6) | N2A—H2A1 | 0.95 (6) |
O13—H13A | 0.83 (2) | N2A—H2A2 | 0.96 (6) |
O14—H14 | 0.94 (5) | N1B—C6B | 1.335 (7) |
O16—H16 | 0.91 (7) | N1B—C2B | 1.342 (6) |
C21—O22 | 1.235 (5) | N1B—H1B | 0.87 (6) |
C21—O21 | 1.262 (5) | C2B—C3B | 1.371 (7) |
C21—C22 | 1.535 (6) | C2B—H2B | 0.9300 |
C22—O23 | 1.398 (6) | C3B—C4B | 1.387 (7) |
C22—C23 | 1.521 (7) | C3B—C7B | 1.505 (7) |
C22—H22 | 0.9800 | C4B—C5B | 1.380 (7) |
C23—O24 | 1.412 (6) | C4B—H4B | 0.9300 |
C23—C24 | 1.522 (6) | C5B—C6B | 1.348 (8) |
C23—H23 | 0.9800 | C5B—H5B | 0.9300 |
C24—O25 | 1.208 (5) | C6B—H6B | 0.9300 |
C24—O26 | 1.309 (6) | C7B—O1B | 1.220 (6) |
O23—H23A | 0.82 (8) | C7B—N2B | 1.318 (7) |
O24—H24 | 0.97 (7) | N2B—H2B1 | 0.86 (9) |
O26—H26 | 0.90 (7) | N2B—H2B2 | 0.95 (6) |
N1A—C2A | 1.319 (7) | O1W—H11W | 0.92 (3) |
N1A—C6A | 1.346 (7) | O1W—H12W | 0.91 (3) |
N1A—H1A | 0.95 (5) | O2W—H21W | 0.91 (3) |
C2A—C3A | 1.387 (7) | O2W—H22W | 0.87 (2) |
O12—C11—O11 | 124.5 (4) | N1A—C2A—H2A | 119.8 |
O12—C11—C12 | 117.7 (4) | C3A—C2A—H2A | 119.8 |
O11—C11—C12 | 117.8 (4) | C2A—C3A—C4A | 118.2 (5) |
O13—C12—C13 | 109.1 (3) | C2A—C3A—C7A | 116.7 (4) |
O13—C12—C11 | 111.4 (4) | C4A—C3A—C7A | 125.0 (5) |
C13—C12—C11 | 109.6 (4) | C5A—C4A—C3A | 119.2 (5) |
O13—C12—H12 | 108.9 | C5A—C4A—H4A | 120.4 |
C13—C12—H12 | 108.9 | C3A—C4A—H4A | 120.4 |
C11—C12—H12 | 108.9 | C6A—C5A—C4A | 120.2 (5) |
O14—C13—C12 | 110.3 (4) | C6A—C5A—H5A | 119.9 |
O14—C13—C14 | 110.7 (3) | C4A—C5A—H5A | 119.9 |
C12—C13—C14 | 111.2 (4) | N1A—C6A—C5A | 119.9 (5) |
O14—C13—H13 | 108.2 | N1A—C6A—H6A | 120.1 |
C12—C13—H13 | 108.2 | C5A—C6A—H6A | 120.1 |
C14—C13—H13 | 108.2 | O1A—C7A—N2A | 123.6 (5) |
O15—C14—O16 | 124.9 (4) | O1A—C7A—C3A | 119.4 (5) |
O15—C14—C13 | 122.2 (5) | N2A—C7A—C3A | 117.0 (5) |
O16—C14—C13 | 112.9 (4) | C7A—N2A—H2A1 | 117 (3) |
C12—O13—H13A | 110 (6) | C7A—N2A—H2A2 | 125 (3) |
C13—O14—H14 | 105 (3) | H2A1—N2A—H2A2 | 116 (5) |
C14—O16—H16 | 114 (5) | C6B—N1B—C2B | 122.0 (5) |
O22—C21—O21 | 125.3 (4) | C6B—N1B—H1B | 115 (3) |
O22—C21—C22 | 117.1 (4) | C2B—N1B—H1B | 123 (4) |
O21—C21—C22 | 117.6 (4) | N1B—C2B—C3B | 120.2 (5) |
O23—C22—C23 | 108.6 (4) | N1B—C2B—H2B | 119.9 |
O23—C22—C21 | 113.7 (4) | C3B—C2B—H2B | 119.9 |
C23—C22—C21 | 108.1 (4) | C2B—C3B—C4B | 118.1 (4) |
O23—C22—H22 | 108.8 | C2B—C3B—C7B | 116.8 (4) |
C23—C22—H22 | 108.8 | C4B—C3B—C7B | 125.0 (5) |
C21—C22—H22 | 108.8 | C5B—C4B—C3B | 119.9 (5) |
O24—C23—C22 | 111.6 (4) | C5B—C4B—H4B | 120.1 |
O24—C23—C24 | 111.3 (4) | C3B—C4B—H4B | 120.1 |
C22—C23—C24 | 110.2 (4) | C6B—C5B—C4B | 119.8 (5) |
O24—C23—H23 | 107.9 | C6B—C5B—H5B | 120.1 |
C22—C23—H23 | 107.9 | C4B—C5B—H5B | 120.1 |
C24—C23—H23 | 107.9 | N1B—C6B—C5B | 120.0 (5) |
O25—C24—O26 | 124.6 (4) | N1B—C6B—H6B | 120.0 |
O25—C24—C23 | 122.7 (4) | C5B—C6B—H6B | 120.0 |
O26—C24—C23 | 112.6 (4) | O1B—C7B—N2B | 123.0 (5) |
C22—O23—H23A | 125 (5) | O1B—C7B—C3B | 119.4 (5) |
C23—O24—H24 | 114 (4) | N2B—C7B—C3B | 117.6 (5) |
C24—O26—H26 | 113 (4) | C7B—N2B—H2B1 | 117 (6) |
C2A—N1A—C6A | 122.0 (5) | C7B—N2B—H2B2 | 122 (3) |
C2A—N1A—H1A | 128 (3) | H2B1—N2B—H2B2 | 119 (7) |
C6A—N1A—H1A | 110 (3) | H11W—O1W—H12W | 99 (3) |
N1A—C2A—C3A | 120.4 (5) | H21W—O2W—H22W | 104 (4) |
O12—C11—C12—O13 | 178.9 (4) | C6A—N1A—C2A—C3A | 0.5 (8) |
O11—C11—C12—O13 | −0.4 (6) | N1A—C2A—C3A—C4A | −0.4 (8) |
O12—C11—C12—C13 | 58.1 (6) | N1A—C2A—C3A—C7A | −178.4 (4) |
O11—C11—C12—C13 | −121.2 (5) | C2A—C3A—C4A—C5A | 0.3 (8) |
O13—C12—C13—O14 | −67.3 (4) | C7A—C3A—C4A—C5A | 178.1 (5) |
C11—C12—C13—O14 | 54.8 (5) | C3A—C4A—C5A—C6A | −0.3 (8) |
O13—C12—C13—C14 | 55.9 (5) | C2A—N1A—C6A—C5A | −0.4 (8) |
C11—C12—C13—C14 | 178.0 (4) | C4A—C5A—C6A—N1A | 0.4 (8) |
O14—C13—C14—O15 | −6.0 (7) | C2A—C3A—C7A—O1A | 22.1 (7) |
C12—C13—C14—O15 | −128.9 (6) | C4A—C3A—C7A—O1A | −155.7 (5) |
O14—C13—C14—O16 | 174.0 (4) | C2A—C3A—C7A—N2A | −159.7 (5) |
C12—C13—C14—O16 | 51.0 (5) | C4A—C3A—C7A—N2A | 22.5 (7) |
O22—C21—C22—O23 | −175.0 (4) | C6B—N1B—C2B—C3B | 0.9 (8) |
O21—C21—C22—O23 | 5.4 (6) | N1B—C2B—C3B—C4B | −0.9 (7) |
O22—C21—C22—C23 | 64.4 (5) | N1B—C2B—C3B—C7B | −178.1 (5) |
O21—C21—C22—C23 | −115.2 (4) | C2B—C3B—C4B—C5B | 0.8 (8) |
O23—C22—C23—O24 | −70.4 (5) | C7B—C3B—C4B—C5B | 177.7 (5) |
C21—C22—C23—O24 | 53.3 (5) | C3B—C4B—C5B—C6B | −0.8 (9) |
O23—C22—C23—C24 | 53.8 (5) | C2B—N1B—C6B—C5B | −0.9 (8) |
C21—C22—C23—C24 | 177.5 (4) | C4B—C5B—C6B—N1B | 0.8 (9) |
O24—C23—C24—O25 | 4.7 (7) | C2B—C3B—C7B—O1B | 7.4 (7) |
C22—C23—C24—O25 | −119.6 (5) | C4B—C3B—C7B—O1B | −169.5 (5) |
O24—C23—C24—O26 | −178.0 (4) | C2B—C3B—C7B—N2B | −173.1 (5) |
C22—C23—C24—O26 | 57.6 (5) | C4B—C3B—C7B—N2B | 9.9 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13A···O1Wi | 0.83 (2) | 1.95 (4) | 2.751 (6) | 162 (9) |
O14—H14···O22 | 0.94 (5) | 1.85 (5) | 2.722 (5) | 154 (4) |
O16—H16···O11ii | 0.91 (7) | 1.67 (7) | 2.573 (4) | 171 (7) |
O23—H23A···O1A | 0.82 (8) | 2.03 (8) | 2.836 (6) | 167 (8) |
O23—H23A···O2Wi | 0.82 (8) | 2.34 (8) | 2.83 (2) | 119 (6) |
O24—H24···O12iii | 0.97 (7) | 1.83 (7) | 2.751 (5) | 158 (6) |
O26—H26···O21ii | 0.90 (7) | 1.67 (7) | 2.567 (5) | 179 (7) |
N1A—H1A···O11 | 0.95 (5) | 1.71 (6) | 2.651 (6) | 168 (5) |
N2A—H2A1···O25iv | 0.95 (6) | 2.00 (6) | 2.952 (6) | 173 (5) |
N2A—H2A2···O12v | 0.96 (6) | 2.02 (6) | 2.977 (6) | 175 (5) |
N1B—H1B···O21 | 0.87 (6) | 1.83 (6) | 2.656 (6) | 158 (5) |
N2B—H2B1···O15iv | 0.86 (9) | 2.09 (9) | 2.946 (6) | 174 (8) |
N2B—H2B2···O22vi | 0.95 (6) | 1.96 (6) | 2.887 (6) | 166 (5) |
O1W—H11W···O14 | 0.92 (3) | 2.00 (5) | 2.835 (5) | 150 (7) |
O1W—H11W···O15 | 0.92 (3) | 2.54 (5) | 3.220 (7) | 132 (5) |
O1W—H12W···O1Bvii | 0.91 (3) | 1.90 (4) | 2.722 (5) | 150 (6) |
O2W—H21W···O1Aviii | 0.91 (3) | 1.62 (2) | 2.46 (2) | 152 (7) |
O2W—H22W···O24ix | 0.87 (2) | 2.01 (1) | 2.87 (2) | 178 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x+1, y, z; (iii) x, y, z−1; (iv) −x+1, y+1/2, −z; (v) −x, y+1/2, −z+1; (vi) −x, y+1/2, −z; (vii) −x+1, y−1/2, −z; (viii) −x+1, y−1/2, −z+1; (ix) x, y, z+1. |
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