Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025918/fb2003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025918/fb2003Isup2.hkl |
CCDC reference: 618965
Data collection: COLLECT (Nonius, 2000); cell refinement: Please supply; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 1999) and PLATON.
C9H12N2O4·0.33H2O | Dx = 1.280 Mg m−3 |
Mr = 218.21 | Melting point = 324.9–325.7 K |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | Cell parameters from 34593 reflections |
a = 16.3410 (14) Å | θ = 5.0–25.1° |
c = 88.12 (6) Å | µ = 0.10 mm−1 |
V = 20379 (13) Å3 | T = 170 K |
Z = 72 | Sphere, colourless |
F(000) = 8304 | 0.5 × 0.5 × 0.5 × 0.25 (radius) mm |
Nonius KappaCCD diffractometer | 2091 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.106 |
Horizontally mounted graphite crystal monochromator | θmax = 25.1°, θmin = 5.0° |
Detector resolution: 9 pixels mm-1 | h = −18→18 |
φ and ω scans | k = −19→19 |
34593 measured reflections | l = −100→105 |
4028 independent reflections |
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)] = 0.086 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0621P)2 + 45.7496P] where P = (Fo2 + 2Fc2)/3 |
4028 reflections | (Δ/σ)max < 0.001 |
294 parameters | Δρmax = 0.35 e Å−3 |
4 restraints | Δρmin = −0.21 e Å−3 |
124 constraints |
Experimental. Several data sets have been collected on different crystals. The first data collection was performed on a four-circle diffractometer with a sequential detector at room temperature. Following data collections were performed on a KappaCCD diffractometer at 170 K in order to reduce the large displacement parameters of the ethoxycarbonyl chains. The present data set corresponds to the whole sphere based on a triclinic unit cell (16.325, 16.354, 30.829 Å, 74.72, 74.66, 60.14°). Reduction of the unit cell (DENZO - Otwinowski & Minor, 1997) leads to R rhombohedral or C monoclinic unit cells. Initially, the structure was solved in the space group C2/c. Presence of six pyrazoles and two water molecules in the asymmetric unit was revealed. Three pairs of pyrazoles were related by a pseudo- threefold axis along the line defined by the two water O atoms. (This axis is a crystallographic axis in the space group R-3c.) The refinements in the C2/c (Rint=0.0998 and 11570 independent reflections) and in the R-3c groups have progressed in a similar way. Both refinements revealed disorder in the ethoxycarbonyl chains in the pyrazole conformers (I) Therefore, we have decided for the simpler description in a trigonal system. (a=28.366, b= 16.325, c=30.858 Å and β=107.924°): Cc or C2/c space groups. In vectorial notation: (A,B,C)=(a,b,c)(-.5. 5 - 1) (. 5. 5 0) (0 0 - 3) (A,B,C) rhombohedral axes (a,b,c) monoclinic axes) |
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 F2against 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. The present data set was obtained from the data collection of the whole sphere based on a triclinic unit cell (16.325, 16.354, 30.829 Å, 74.72, 74.66, 60.14°). Reduction of the unit cell (Otwinowski & Minor, 1997) leads to a R rhombohedral or C monoclinic unit cell. Initially, the structure was solved in C2/c (Rint = 0.0998, 11570 independent reflections). The structure solution in C2/c revealed the presence of six pyrazoles and two water molecules in the asymmetric unit. Three pairs of pyrazoles were related by a pseudo-threefold axis along the line occupied by the water O atoms. (This axis is the crystallographic one in space group R3c.) The refinement in C2/c [890 parameters, 12 restraints, R = 0.0743 for 4232 observed reflections (I>2σ(I)], as well as in R3c progressed in a similar way, with disorder of the ethoxycarbonyl chain in the pyrazole conformers (I). The structure description in R3c is preferred for its simplicity. The disorder in the pyrazole confomer (I) has been modelled as split over two orientations. A restraint on the O—CH2 and CH2—CH3 distances between the non-H atoms in both disordered chains was applied. DFIX was set to 1.470 (5) Å. This value was retrieved from 150 structures measured between 160 and 180 K that are contained in the CSD. The occupancy factors equalled 0.77 (2) and 0.23 (2) for the major and minor components, respectively. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ow1 | 0.0000 | 0.0000 | 0.11749 (5) | 0.0460 (13) | |
H1W1 | 0.0000 | 0.0000 | 0.1273 | 0.055* | |
H2W1 | −0.0016 | 0.0491 | 0.1143 | 0.055* | 0.33 |
Ow2 | 0.0000 | 0.0000 | 0.14857 (5) | 0.0488 (13) | |
H1W2 | 0.0492 | 0.0453 | 0.1521 | 0.059* | 0.67 |
N1A | 0.0166 (2) | 0.1773 (2) | 0.11356 (4) | 0.0450 (9) | |
H1A | 0.0056 | 0.1189 | 0.1131 | 0.054* | 0.67 |
N2A | 0.0832 (2) | 0.2460 (3) | 0.12204 (4) | 0.0458 (9) | |
H2A | 0.1237 | 0.2413 | 0.1280 | 0.055* | 0.33 |
C3A | 0.0768 (3) | 0.3240 (3) | 0.11969 (5) | 0.0490 (12) | |
C4A | 0.0066 (3) | 0.3053 (3) | 0.10956 (5) | 0.0557 (13) | |
H4A | −0.0124 | 0.3478 | 0.1058 | 0.067* | |
C5A | −0.0308 (3) | 0.2114 (3) | 0.10592 (5) | 0.0465 (12) | |
C6A | 0.1413 (4) | 0.4171 (4) | 0.12684 (6) | 0.0643 (14) | |
O7A | 0.1364 (3) | 0.4859 (3) | 0.12479 (5) | 0.0996 (14) | |
O8A | 0.2050 (2) | 0.4111 (2) | 0.13535 (4) | 0.0731 (10) | |
C9A | 0.2786 (4) | 0.5034 (4) | 0.14151 (8) | 0.106 (2) | |
H91A | 0.3071 | 0.5505 | 0.1333 | 0.127* | |
H92A | 0.2509 | 0.5272 | 0.1491 | 0.127* | |
C10A | 0.3491 (4) | 0.4869 (4) | 0.14849 (8) | 0.110 (2) | |
H101A | 0.3990 | 0.5460 | 0.1529 | 0.165* | |
H102A | 0.3764 | 0.4642 | 0.1408 | 0.165* | |
H20C | 0.3197 | 0.4393 | 0.1565 | 0.165* | |
C11A | −0.1091 (4) | 0.1528 (4) | 0.09563 (6) | 0.0692 (16) | |
O12A | −0.1448 (7) | 0.1879 (5) | 0.08766 (10) | 0.087 (3) | 0.774 (15) |
O12'A | −0.1789 (13) | 0.1611 (13) | 0.0939 (2) | 0.043 (6)* | 0.226 (15) |
O13A | −0.1276 (6) | 0.0623 (4) | 0.09554 (10) | 0.0567 (19) | 0.774 (15) |
O13'A | −0.1049 (14) | 0.0780 (10) | 0.0908 (2) | 0.050 (8)* | 0.226 (15) |
C14A | −0.2021 (6) | −0.0069 (8) | 0.08576 (12) | 0.069 (3) | 0.774 (15) |
H141A | −0.2377 | 0.0211 | 0.0811 | 0.083* | 0.774 (15) |
H142A | −0.2467 | −0.0626 | 0.0918 | 0.083* | 0.774 (15) |
C14'A | −0.1740 (17) | 0.0273 (13) | 0.0787 (3) | 0.040 (7)* | 0.226 (15) |
H141'A | −0.1448 | 0.0492 | 0.0686 | 0.048* | 0.226 (15) |
H142'A | −0.2287 | 0.0374 | 0.0796 | 0.048* | 0.226 (15) |
C15A | −0.1585 (8) | −0.0365 (9) | 0.07360 (12) | 0.103 (4) | 0.774 (15) |
H151A | −0.2084 | −0.0851 | 0.0673 | 0.154* | 0.774 (15) |
H152A | −0.1216 | −0.0622 | 0.0783 | 0.154* | 0.774 (15) |
H153A | −0.1170 | 0.0183 | 0.0673 | 0.154* | 0.774 (15) |
C15'A | −0.204 (2) | −0.0729 (14) | 0.0809 (4) | 0.082 (11)* | 0.226 (15) |
H151'A | −0.2526 | −0.1115 | 0.0735 | 0.123* | 0.226 (15) |
H152'A | −0.2286 | −0.0922 | 0.0912 | 0.123* | 0.226 (15) |
H153'A | −0.1490 | −0.0819 | 0.0795 | 0.123* | 0.226 (15) |
N1B | 0.2220 (2) | 0.2014 (2) | 0.13493 (4) | 0.0441 (9) | |
H1B | 0.1871 | 0.2246 | 0.1315 | 0.053* | 0.67 |
N2B | 0.1932 (2) | 0.1299 (2) | 0.14460 (4) | 0.0416 (9) | |
H2B | 0.1367 | 0.0982 | 0.1487 | 0.050* | 0.33 |
C3B | 0.2656 (3) | 0.1149 (3) | 0.14694 (5) | 0.0425 (11) | |
C4B | 0.3424 (3) | 0.1787 (3) | 0.13863 (5) | 0.0470 (12) | |
H4B | 0.4031 | 0.1841 | 0.1382 | 0.056* | |
C5B | 0.3127 (3) | 0.2328 (3) | 0.13110 (5) | 0.0430 (11) | |
C6B | 0.2559 (3) | 0.0371 (3) | 0.15652 (5) | 0.0537 (12) | |
O7B | 0.3171 (2) | 0.0171 (2) | 0.15813 (4) | 0.0774 (11) | |
O8B | 0.1713 (2) | −0.0082 (2) | 0.16302 (4) | 0.0679 (10) | |
C9B | 0.1518 (4) | −0.0885 (4) | 0.17270 (7) | 0.0908 (19) | |
H91B | 0.2074 | −0.0728 | 0.1791 | 0.109* | |
H92B | 0.1384 | −0.1439 | 0.1664 | 0.109* | |
C10B | 0.0698 (4) | −0.1105 (4) | 0.18226 (6) | 0.095 (2) | |
H101B | 0.0553 | −0.1648 | 0.1887 | 0.142* | |
H102B | 0.0153 | −0.1255 | 0.1758 | 0.142* | |
H103B | 0.0842 | −0.0557 | 0.1886 | 0.142* | |
C11B | 0.3593 (3) | 0.3094 (3) | 0.12018 (5) | 0.0528 (12) | |
O12B | 0.3202 (2) | 0.3435 (2) | 0.11311 (4) | 0.0717 (11) | |
O13B | 0.4500 (2) | 0.3361 (2) | 0.11858 (4) | 0.0653 (10) | |
C14B | 0.5027 (4) | 0.4107 (4) | 0.10744 (7) | 0.0814 (17) | |
H141B | 0.4699 | 0.3929 | 0.0975 | 0.098* | |
H142B | 0.5068 | 0.4704 | 0.1108 | 0.098* | |
C15B | 0.5977 (4) | 0.4237 (4) | 0.10591 (6) | 0.0843 (17) | |
H151B | 0.6334 | 0.4731 | 0.0984 | 0.127* | |
H152B | 0.5932 | 0.3643 | 0.1026 | 0.127* | |
H153B | 0.6302 | 0.4425 | 0.1157 | 0.127* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ow1 | 0.0434 (18) | 0.0434 (18) | 0.051 (3) | 0.0217 (9) | 0.000 | 0.000 |
Ow2 | 0.0375 (17) | 0.0375 (17) | 0.071 (4) | 0.0187 (9) | 0.000 | 0.000 |
N1A | 0.044 (2) | 0.040 (2) | 0.048 (2) | 0.0190 (19) | −0.0125 (19) | −0.0069 (19) |
N2A | 0.042 (2) | 0.050 (2) | 0.050 (2) | 0.027 (2) | −0.0160 (18) | −0.0074 (19) |
C3A | 0.046 (3) | 0.048 (3) | 0.053 (3) | 0.023 (2) | −0.004 (2) | −0.004 (2) |
C4A | 0.059 (3) | 0.051 (3) | 0.066 (3) | 0.035 (3) | −0.019 (3) | −0.006 (3) |
C5A | 0.051 (3) | 0.052 (3) | 0.048 (3) | 0.034 (3) | −0.018 (2) | −0.007 (2) |
C6A | 0.059 (3) | 0.060 (4) | 0.083 (4) | 0.037 (3) | −0.022 (3) | −0.016 (3) |
O7A | 0.112 (3) | 0.058 (2) | 0.140 (4) | 0.051 (2) | −0.045 (3) | −0.033 (2) |
O8A | 0.061 (2) | 0.060 (2) | 0.092 (2) | 0.026 (2) | −0.028 (2) | −0.0303 (19) |
C9A | 0.125 (6) | 0.067 (4) | 0.122 (5) | 0.045 (4) | −0.061 (5) | −0.034 (4) |
C10A | 0.091 (5) | 0.080 (4) | 0.136 (6) | 0.026 (4) | −0.058 (4) | −0.020 (4) |
C11A | 0.065 (4) | 0.077 (4) | 0.083 (4) | 0.049 (3) | −0.035 (3) | −0.028 (3) |
O12A | 0.095 (6) | 0.097 (5) | 0.095 (6) | 0.068 (5) | −0.059 (5) | −0.020 (4) |
O13A | 0.050 (4) | 0.060 (3) | 0.064 (4) | 0.030 (3) | −0.025 (4) | −0.019 (3) |
C14A | 0.052 (5) | 0.067 (6) | 0.077 (6) | 0.021 (4) | −0.029 (5) | −0.018 (5) |
C15A | 0.087 (7) | 0.131 (9) | 0.091 (8) | 0.054 (7) | −0.046 (6) | −0.066 (7) |
N1B | 0.041 (2) | 0.045 (2) | 0.046 (2) | 0.0219 (19) | −0.0070 (18) | 0.0096 (19) |
N2B | 0.032 (2) | 0.046 (2) | 0.041 (2) | 0.0156 (18) | −0.0011 (17) | 0.0050 (18) |
C3B | 0.034 (3) | 0.037 (3) | 0.046 (3) | 0.009 (2) | −0.005 (2) | 0.008 (2) |
C4B | 0.033 (3) | 0.052 (3) | 0.054 (3) | 0.020 (2) | −0.005 (2) | 0.011 (2) |
C5B | 0.030 (3) | 0.043 (3) | 0.052 (3) | 0.014 (2) | −0.003 (2) | 0.011 (2) |
C6B | 0.042 (3) | 0.050 (3) | 0.059 (3) | 0.015 (3) | 0.001 (3) | 0.009 (3) |
O7B | 0.059 (2) | 0.081 (3) | 0.095 (3) | 0.037 (2) | 0.010 (2) | 0.043 (2) |
O8B | 0.052 (2) | 0.064 (2) | 0.077 (2) | 0.0214 (18) | 0.0124 (18) | 0.0373 (19) |
C9B | 0.077 (4) | 0.084 (4) | 0.102 (5) | 0.033 (4) | 0.017 (4) | 0.047 (4) |
C10B | 0.079 (4) | 0.086 (4) | 0.070 (4) | 0.004 (3) | 0.001 (3) | 0.029 (3) |
C11B | 0.046 (3) | 0.055 (3) | 0.058 (3) | 0.025 (3) | −0.002 (3) | 0.013 (3) |
O12B | 0.057 (2) | 0.075 (2) | 0.088 (3) | 0.037 (2) | 0.0035 (19) | 0.038 (2) |
O13B | 0.041 (2) | 0.071 (2) | 0.080 (2) | 0.0245 (18) | 0.0093 (17) | 0.0408 (18) |
C14B | 0.069 (4) | 0.078 (4) | 0.095 (4) | 0.036 (3) | 0.019 (3) | 0.046 (3) |
C15B | 0.069 (4) | 0.093 (4) | 0.095 (4) | 0.044 (4) | 0.028 (3) | 0.037 (4) |
Ow1—H1W1 | 0.8647 | C15A—H151A | 0.9800 |
Ow1—H2W1 | 0.8634 | C15A—H152A | 0.9800 |
Ow2—H1W2 | 0.8342 | C15A—H153A | 0.9800 |
N1A—N2A | 1.335 (4) | C15'A—H151'A | 0.9800 |
N1A—C5A | 1.340 (5) | C15'A—H152'A | 0.9800 |
N1A—H1A | 0.8800 | C15'A—H153'A | 0.9800 |
N2A—C3A | 1.346 (5) | N1B—N2B | 1.327 (4) |
N2A—H2A | 0.8800 | N1B—C5B | 1.347 (5) |
C3A—C4A | 1.362 (6) | N1B—H1B | 0.8800 |
C3A—C6A | 1.490 (6) | N2B—C3B | 1.340 (5) |
C4A—C5A | 1.375 (6) | N2B—H2B | 0.8800 |
C4A—H4A | 0.9500 | C3B—C4B | 1.374 (5) |
C5A—C11A | 1.466 (6) | C3B—C6B | 1.466 (6) |
C6A—O7A | 1.181 (5) | C4B—C5B | 1.374 (5) |
C6A—O8A | 1.325 (5) | C4B—H4B | 0.9500 |
O8A—C9A | 1.484 (6) | C5B—C11B | 1.456 (6) |
C9A—C10A | 1.445 (10) | C6B—O7B | 1.208 (5) |
C9A—H91A | 0.9900 | C6B—O8B | 1.328 (5) |
C9A—H92A | 0.9900 | O8B—C9B | 1.461 (6) |
C10A—H101A | 0.9800 | C9B—C10B | 1.467 (7) |
C10A—H102A | 0.9800 | C9B—H91B | 0.9900 |
C10A—H20C | 0.9800 | C9B—H92B | 0.9900 |
C11A—O12'A | 1.224 (19) | C10B—H101B | 0.9800 |
C11A—O12A | 1.225 (7) | C10B—H102B | 0.9800 |
C11A—O13'A | 1.329 (5) | C10B—H103B | 0.9800 |
C11A—O13A | 1.353 (7) | C11B—O12B | 1.209 (5) |
O13A—C14A | 1.458 (7) | C11B—O13B | 1.327 (5) |
O13'A—C14'A | 1.470 (4) | O13B—C14B | 1.464 (5) |
C14A—C15A | 1.495 (12) | C14B—C15B | 1.464 (6) |
C14A—H141A | 0.9900 | C14B—H141B | 0.9900 |
C14A—H142A | 0.9900 | C14B—H142B | 0.9900 |
C14'A—C15'A | 1.471 (5) | C15B—H151B | 0.9800 |
C14'A—H141'A | 0.9900 | C15B—H152B | 0.9800 |
C14'A—H142'A | 0.9900 | C15B—H153B | 0.9800 |
H1W1—Ow1—H2W1 | 109.2 | C14A—C15A—H153A | 109.5 |
H1W2i—Ow2—H1W2 | 107.0 | H151A—C15A—H153A | 109.5 |
N2A—N1A—C5A | 109.2 (3) | H152A—C15A—H153A | 109.5 |
N2A—N1A—H1A | 125.4 | C14'A—C15'A—H151'A | 109.5 |
C5A—N1A—H1A | 125.4 | C14'A—C15'A—H152'A | 109.5 |
N1A—N2A—C3A | 107.1 (3) | H151'A—C15'A—H152'A | 109.5 |
N1A—N2A—H2A | 126.5 | C14'A—C15'A—H153'A | 109.5 |
C3A—N2A—H2A | 126.5 | H151'A—C15'A—H153'A | 109.5 |
N2A—C3A—C4A | 110.1 (4) | H152'A—C15'A—H153'A | 109.5 |
N2A—C3A—C6A | 123.4 (4) | N2B—N1B—C5B | 109.5 (3) |
C4A—C3A—C6A | 126.4 (4) | N2B—N1B—H1B | 125.2 |
C3A—C4A—C5A | 104.9 (4) | C5B—N1B—H1B | 125.2 |
C3A—C4A—H4A | 127.5 | N1B—N2B—C3B | 107.7 (3) |
C5A—C4A—H4A | 127.5 | N1B—N2B—H2B | 126.2 |
N1A—C5A—C4A | 108.6 (4) | C3B—N2B—H2B | 126.2 |
N1A—C5A—C11A | 122.4 (4) | N2B—C3B—C4B | 109.5 (4) |
C4A—C5A—C11A | 129.0 (4) | N2B—C3B—C6B | 121.6 (4) |
O7A—C6A—O8A | 125.9 (5) | C4B—C3B—C6B | 128.8 (4) |
O7A—C6A—C3A | 123.9 (5) | C5B—C4B—C3B | 105.2 (4) |
O8A—C6A—C3A | 110.2 (4) | C5B—C4B—H4B | 127.4 |
C6A—O8A—C9A | 113.6 (4) | C3B—C4B—H4B | 127.4 |
C10A—C9A—O8A | 106.5 (4) | N1B—C5B—C4B | 108.1 (4) |
C10A—C9A—H91A | 110.4 | N1B—C5B—C11B | 119.7 (4) |
O8A—C9A—H91A | 110.4 | C4B—C5B—C11B | 132.2 (4) |
C10A—C9A—H92A | 110.4 | O7B—C6B—O8B | 124.8 (4) |
O8A—C9A—H92A | 110.4 | O7B—C6B—C3B | 123.9 (4) |
H91A—C9A—H92A | 108.6 | O8B—C6B—C3B | 111.3 (4) |
C9A—C10A—H101A | 109.5 | C6B—O8B—C9B | 116.8 (4) |
C9A—C10A—H102A | 109.5 | O8B—C9B—C10B | 108.5 (5) |
H101A—C10A—H102A | 109.5 | O8B—C9B—H91B | 110.0 |
C9A—C10A—H20C | 109.5 | C10B—C9B—H91B | 110.0 |
H101A—C10A—H20C | 109.5 | O8B—C9B—H92B | 110.0 |
H102A—C10A—H20C | 109.5 | C10B—C9B—H92B | 110.0 |
O12'A—C11A—O13'A | 122.9 (13) | H91B—C9B—H92B | 108.4 |
O12A—C11A—O13'A | 120.2 (10) | C9B—C10B—H101B | 109.5 |
O12A—C11A—O13A | 127.6 (5) | C9B—C10B—H102B | 109.5 |
O12'A—C11A—C5A | 124.0 (9) | H101B—C10B—H102B | 109.5 |
O12A—C11A—C5A | 120.8 (5) | C9B—C10B—H103B | 109.5 |
O13'A—C11A—C5A | 111.7 (9) | H101B—C10B—H103B | 109.5 |
O13A—C11A—C5A | 111.3 (4) | H102B—C10B—H103B | 109.5 |
C11A—O13A—C14A | 119.7 (6) | O12B—C11B—O13B | 123.7 (4) |
C11A—O13'A—C14'A | 111.8 (14) | O12B—C11B—C5B | 124.6 (4) |
O13A—C14A—C15A | 109.0 (6) | O13B—C11B—C5B | 111.7 (4) |
O13A—C14A—H141A | 109.9 | C11B—O13B—C14B | 116.1 (3) |
C15A—C14A—H141A | 109.9 | C15B—C14B—O13B | 108.8 (4) |
O13A—C14A—H142A | 109.9 | C15B—C14B—H141B | 109.9 |
C15A—C14A—H142A | 109.9 | O13B—C14B—H141B | 109.9 |
H141A—C14A—H142A | 108.3 | C15B—C14B—H142B | 109.9 |
O13'A—C14'A—C15'A | 105.2 (19) | O13B—C14B—H142B | 109.9 |
O13'A—C14'A—H141'A | 110.7 | H141B—C14B—H142B | 108.3 |
C15'A—C14'A—H141'A | 110.7 | C14B—C15B—H151B | 109.5 |
O13'A—C14'A—H142'A | 110.7 | C14B—C15B—H152B | 109.5 |
C15'A—C14'A—H142'A | 110.7 | H151B—C15B—H152B | 109.5 |
H141'A—C14'A—H142'A | 108.8 | C14B—C15B—H153B | 109.5 |
C14A—C15A—H151A | 109.5 | H151B—C15B—H153B | 109.5 |
C14A—C15A—H152A | 109.5 | H152B—C15B—H153B | 109.5 |
H151A—C15A—H152A | 109.5 | ||
C5A—N1A—N2A—C3A | 0.3 (5) | C5A—C11A—O13'A—C14'A | −171.1 (14) |
N1A—N2A—C3A—C4A | −0.7 (5) | C11A—O13A—C14A—C15A | 112.5 (15) |
N1A—N2A—C3A—C6A | −178.2 (4) | C11A—O13'A—C14'A—C15'A | −146 (3) |
N2A—C3A—C4A—C5A | 0.8 (5) | C5B—N1B—N2B—C3B | −0.4 (4) |
C6A—C3A—C4A—C5A | 178.2 (4) | N1B—N2B—C3B—C4B | 0.4 (5) |
N2A—N1A—C5A—C4A | 0.2 (5) | N1B—N2B—C3B—C6B | −176.8 (4) |
N2A—N1A—C5A—C11A | −179.7 (5) | N2B—C3B—C4B—C5B | −0.2 (5) |
C3A—C4A—C5A—N1A | −0.6 (5) | C6B—C3B—C4B—C5B | 176.7 (4) |
C3A—C4A—C5A—C11A | 179.3 (5) | N2B—N1B—C5B—C4B | 0.3 (5) |
N2A—C3A—C6A—O7A | 179.7 (5) | N2B—N1B—C5B—C11B | 178.1 (4) |
C4A—C3A—C6A—O7A | 2.6 (9) | C3B—C4B—C5B—N1B | 0.0 (5) |
N2A—C3A—C6A—O8A | 1.2 (7) | C3B—C4B—C5B—C11B | −177.4 (4) |
C4A—C3A—C6A—O8A | −175.9 (4) | N2B—C3B—C6B—O7B | 174.9 (4) |
O7A—C6A—O8A—C9A | −4.9 (8) | C4B—C3B—C6B—O7B | −1.7 (8) |
C3A—C6A—O8A—C9A | 173.5 (4) | N2B—C3B—C6B—O8B | −4.7 (6) |
C6A—O8A—C9A—C10A | −171.6 (5) | C4B—C3B—C6B—O8B | 178.7 (4) |
N1A—C5A—C11A—O12'A | 145.0 (12) | O7B—C6B—O8B—C9B | −0.5 (7) |
C4A—C5A—C11A—O12'A | −34.8 (14) | C3B—C6B—O8B—C9B | 179.1 (4) |
N1A—C5A—C11A—O12A | −172.6 (8) | C6B—O8B—C9B—C10B | 163.1 (4) |
C4A—C5A—C11A—O12A | 7.6 (11) | N1B—C5B—C11B—O12B | −6.2 (7) |
N1A—C5A—C11A—O13'A | −22.2 (13) | C4B—C5B—C11B—O12B | 170.9 (5) |
C4A—C5A—C11A—O13'A | 158.0 (11) | N1B—C5B—C11B—O13B | 175.3 (4) |
N1A—C5A—C11A—O13A | 2.5 (9) | C4B—C5B—C11B—O13B | −7.5 (7) |
C4A—C5A—C11A—O13A | −177.4 (7) | O12B—C11B—O13B—C14B | −0.5 (7) |
O12A—C11A—O13A—C14A | −4.2 (13) | C5B—C11B—O13B—C14B | 178.0 (4) |
C5A—C11A—O13A—C14A | −178.8 (6) | C11B—O13B—C14B—C15B | −173.7 (5) |
O12'A—C11A—O13'A—C14'A | 22 (2) |
Symmetry code: (i) −y, x−y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
Ow2—H1W2···N2B | 0.83 | 2.15 | 2.810 (3) | 136 |
N1B—H1B···N2A | 0.88 | 2.07 | 2.936 (5) | 166 |
N1A—H1A···Ow1 | 0.88 | 1.94 | 2.793 (3) | 164 |
Ow1—H1W1···Ow2 | 0.86 | 1.87 | 2.739 (7) | 180 |
N2A—H2A···N1B | 0.88 | 2.10 | 2.936 (5) | 158 |
N2B—H2B···Ow2 | 0.88 | 2.00 | 2.810 (3) | 153 |
Ow1—H2W1···N1A | 0.86 | 1.96 | 2.793 (3) | 161 |