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In the title structure, C9H12N2O4·0.33H2O, the mol­ecules are present as two conformers, one of which is disordered. Another type of disorder involves N—N—H/H—N—N tautomerism. Two crystallographically independent water mol­ecules reside on a threefold axis and some water H atoms are also disordered. Six diethyl 1H-pyrazole-3,5-dicarboxyl­ate mol­ecules (three pairs of conformers) and two water mol­ecules are assembled into a supra­molecular aggregate via N—H...N, Ow—H...N, Ow—H...Ow and N—H...Ow hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025918/fb2003sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025918/fb2003Isup2.hkl
Contains datablock I

CCDC reference: 618965

Key indicators

  • Single-crystal X-ray study
  • T = 170 K
  • Mean [sigma](C-C) = 0.008 Å
  • Disorder in main residue
  • R factor = 0.086
  • wR factor = 0.198
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.106 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.33 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.75 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.44 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14'A PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.52 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.36 PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 29
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C9 H12.67 N2 O4.33 Atom count from _chemical_formula_moiety:C9 H12.66 N2 O4.33 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies. From the CIF: _cell_formula_units_Z 72 From the CIF: _chemical_formula_sum C9 H12.67 N2 O4.33 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 648.00 648.00 0.00 H 912.24 912.00 0.24 N 144.00 144.00 0.00 O 311.76 312.00 -0.24
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

diethyl 1H-pyrazole-3,5-dicarboxylate 0.33-hydrate top
Crystal data top
C9H12N2O4·0.33H2ODx = 1.280 Mg m3
Mr = 218.21Melting point = 324.9–325.7 K
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cCell parameters from 34593 reflections
a = 16.3410 (14) Åθ = 5.0–25.1°
c = 88.12 (6) ŵ = 0.10 mm1
V = 20379 (13) Å3T = 170 K
Z = 72Sphere, colourless
F(000) = 83040.5 × 0.5 × 0.5 × 0.25 (radius) mm
Data collection top
Nonius KappaCCD
diffractometer
2091 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.106
Horizontally mounted graphite crystal monochromatorθmax = 25.1°, θmin = 5.0°
Detector resolution: 9 pixels mm-1h = 1818
φ and ω scansk = 1919
34593 measured reflectionsl = 100105
4028 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.086Hydrogen site location: difference Fourier map
wR(F2) = 0.198H-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 parametersΔρmax = 0.35 e Å3
4 restraintsΔρmin = 0.21 e Å3
124 constraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ow10.00000.00000.11749 (5)0.0460 (13)
H1W10.00000.00000.12730.055*
H2W10.00160.04910.11430.055*0.33
Ow20.00000.00000.14857 (5)0.0488 (13)
H1W20.04920.04530.15210.059*0.67
N1A0.0166 (2)0.1773 (2)0.11356 (4)0.0450 (9)
H1A0.00560.11890.11310.054*0.67
N2A0.0832 (2)0.2460 (3)0.12204 (4)0.0458 (9)
H2A0.12370.24130.12800.055*0.33
C3A0.0768 (3)0.3240 (3)0.11969 (5)0.0490 (12)
C4A0.0066 (3)0.3053 (3)0.10956 (5)0.0557 (13)
H4A0.01240.34780.10580.067*
C5A0.0308 (3)0.2114 (3)0.10592 (5)0.0465 (12)
C6A0.1413 (4)0.4171 (4)0.12684 (6)0.0643 (14)
O7A0.1364 (3)0.4859 (3)0.12479 (5)0.0996 (14)
O8A0.2050 (2)0.4111 (2)0.13535 (4)0.0731 (10)
C9A0.2786 (4)0.5034 (4)0.14151 (8)0.106 (2)
H91A0.30710.55050.13330.127*
H92A0.25090.52720.14910.127*
C10A0.3491 (4)0.4869 (4)0.14849 (8)0.110 (2)
H101A0.39900.54600.15290.165*
H102A0.37640.46420.14080.165*
H20C0.31970.43930.15650.165*
C11A0.1091 (4)0.1528 (4)0.09563 (6)0.0692 (16)
O12A0.1448 (7)0.1879 (5)0.08766 (10)0.087 (3)0.774 (15)
O12'A0.1789 (13)0.1611 (13)0.0939 (2)0.043 (6)*0.226 (15)
O13A0.1276 (6)0.0623 (4)0.09554 (10)0.0567 (19)0.774 (15)
O13'A0.1049 (14)0.0780 (10)0.0908 (2)0.050 (8)*0.226 (15)
C14A0.2021 (6)0.0069 (8)0.08576 (12)0.069 (3)0.774 (15)
H141A0.23770.02110.08110.083*0.774 (15)
H142A0.24670.06260.09180.083*0.774 (15)
C14'A0.1740 (17)0.0273 (13)0.0787 (3)0.040 (7)*0.226 (15)
H141'A0.14480.04920.06860.048*0.226 (15)
H142'A0.22870.03740.07960.048*0.226 (15)
C15A0.1585 (8)0.0365 (9)0.07360 (12)0.103 (4)0.774 (15)
H151A0.20840.08510.06730.154*0.774 (15)
H152A0.12160.06220.07830.154*0.774 (15)
H153A0.11700.01830.06730.154*0.774 (15)
C15'A0.204 (2)0.0729 (14)0.0809 (4)0.082 (11)*0.226 (15)
H151'A0.25260.11150.07350.123*0.226 (15)
H152'A0.22860.09220.09120.123*0.226 (15)
H153'A0.14900.08190.07950.123*0.226 (15)
N1B0.2220 (2)0.2014 (2)0.13493 (4)0.0441 (9)
H1B0.18710.22460.13150.053*0.67
N2B0.1932 (2)0.1299 (2)0.14460 (4)0.0416 (9)
H2B0.13670.09820.14870.050*0.33
C3B0.2656 (3)0.1149 (3)0.14694 (5)0.0425 (11)
C4B0.3424 (3)0.1787 (3)0.13863 (5)0.0470 (12)
H4B0.40310.18410.13820.056*
C5B0.3127 (3)0.2328 (3)0.13110 (5)0.0430 (11)
C6B0.2559 (3)0.0371 (3)0.15652 (5)0.0537 (12)
O7B0.3171 (2)0.0171 (2)0.15813 (4)0.0774 (11)
O8B0.1713 (2)0.0082 (2)0.16302 (4)0.0679 (10)
C9B0.1518 (4)0.0885 (4)0.17270 (7)0.0908 (19)
H91B0.20740.07280.17910.109*
H92B0.13840.14390.16640.109*
C10B0.0698 (4)0.1105 (4)0.18226 (6)0.095 (2)
H101B0.05530.16480.18870.142*
H102B0.01530.12550.17580.142*
H103B0.08420.05570.18860.142*
C11B0.3593 (3)0.3094 (3)0.12018 (5)0.0528 (12)
O12B0.3202 (2)0.3435 (2)0.11311 (4)0.0717 (11)
O13B0.4500 (2)0.3361 (2)0.11858 (4)0.0653 (10)
C14B0.5027 (4)0.4107 (4)0.10744 (7)0.0814 (17)
H141B0.46990.39290.09750.098*
H142B0.50680.47040.11080.098*
C15B0.5977 (4)0.4237 (4)0.10591 (6)0.0843 (17)
H151B0.63340.47310.09840.127*
H152B0.59320.36430.10260.127*
H153B0.63020.44250.11570.127*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ow10.0434 (18)0.0434 (18)0.051 (3)0.0217 (9)0.0000.000
Ow20.0375 (17)0.0375 (17)0.071 (4)0.0187 (9)0.0000.000
N1A0.044 (2)0.040 (2)0.048 (2)0.0190 (19)0.0125 (19)0.0069 (19)
N2A0.042 (2)0.050 (2)0.050 (2)0.027 (2)0.0160 (18)0.0074 (19)
C3A0.046 (3)0.048 (3)0.053 (3)0.023 (2)0.004 (2)0.004 (2)
C4A0.059 (3)0.051 (3)0.066 (3)0.035 (3)0.019 (3)0.006 (3)
C5A0.051 (3)0.052 (3)0.048 (3)0.034 (3)0.018 (2)0.007 (2)
C6A0.059 (3)0.060 (4)0.083 (4)0.037 (3)0.022 (3)0.016 (3)
O7A0.112 (3)0.058 (2)0.140 (4)0.051 (2)0.045 (3)0.033 (2)
O8A0.061 (2)0.060 (2)0.092 (2)0.026 (2)0.028 (2)0.0303 (19)
C9A0.125 (6)0.067 (4)0.122 (5)0.045 (4)0.061 (5)0.034 (4)
C10A0.091 (5)0.080 (4)0.136 (6)0.026 (4)0.058 (4)0.020 (4)
C11A0.065 (4)0.077 (4)0.083 (4)0.049 (3)0.035 (3)0.028 (3)
O12A0.095 (6)0.097 (5)0.095 (6)0.068 (5)0.059 (5)0.020 (4)
O13A0.050 (4)0.060 (3)0.064 (4)0.030 (3)0.025 (4)0.019 (3)
C14A0.052 (5)0.067 (6)0.077 (6)0.021 (4)0.029 (5)0.018 (5)
C15A0.087 (7)0.131 (9)0.091 (8)0.054 (7)0.046 (6)0.066 (7)
N1B0.041 (2)0.045 (2)0.046 (2)0.0219 (19)0.0070 (18)0.0096 (19)
N2B0.032 (2)0.046 (2)0.041 (2)0.0156 (18)0.0011 (17)0.0050 (18)
C3B0.034 (3)0.037 (3)0.046 (3)0.009 (2)0.005 (2)0.008 (2)
C4B0.033 (3)0.052 (3)0.054 (3)0.020 (2)0.005 (2)0.011 (2)
C5B0.030 (3)0.043 (3)0.052 (3)0.014 (2)0.003 (2)0.011 (2)
C6B0.042 (3)0.050 (3)0.059 (3)0.015 (3)0.001 (3)0.009 (3)
O7B0.059 (2)0.081 (3)0.095 (3)0.037 (2)0.010 (2)0.043 (2)
O8B0.052 (2)0.064 (2)0.077 (2)0.0214 (18)0.0124 (18)0.0373 (19)
C9B0.077 (4)0.084 (4)0.102 (5)0.033 (4)0.017 (4)0.047 (4)
C10B0.079 (4)0.086 (4)0.070 (4)0.004 (3)0.001 (3)0.029 (3)
C11B0.046 (3)0.055 (3)0.058 (3)0.025 (3)0.002 (3)0.013 (3)
O12B0.057 (2)0.075 (2)0.088 (3)0.037 (2)0.0035 (19)0.038 (2)
O13B0.041 (2)0.071 (2)0.080 (2)0.0245 (18)0.0093 (17)0.0408 (18)
C14B0.069 (4)0.078 (4)0.095 (4)0.036 (3)0.019 (3)0.046 (3)
C15B0.069 (4)0.093 (4)0.095 (4)0.044 (4)0.028 (3)0.037 (4)
Geometric parameters (Å, º) top
Ow1—H1W10.8647C15A—H151A0.9800
Ow1—H2W10.8634C15A—H152A0.9800
Ow2—H1W20.8342C15A—H153A0.9800
N1A—N2A1.335 (4)C15'A—H151'A0.9800
N1A—C5A1.340 (5)C15'A—H152'A0.9800
N1A—H1A0.8800C15'A—H153'A0.9800
N2A—C3A1.346 (5)N1B—N2B1.327 (4)
N2A—H2A0.8800N1B—C5B1.347 (5)
C3A—C4A1.362 (6)N1B—H1B0.8800
C3A—C6A1.490 (6)N2B—C3B1.340 (5)
C4A—C5A1.375 (6)N2B—H2B0.8800
C4A—H4A0.9500C3B—C4B1.374 (5)
C5A—C11A1.466 (6)C3B—C6B1.466 (6)
C6A—O7A1.181 (5)C4B—C5B1.374 (5)
C6A—O8A1.325 (5)C4B—H4B0.9500
O8A—C9A1.484 (6)C5B—C11B1.456 (6)
C9A—C10A1.445 (10)C6B—O7B1.208 (5)
C9A—H91A0.9900C6B—O8B1.328 (5)
C9A—H92A0.9900O8B—C9B1.461 (6)
C10A—H101A0.9800C9B—C10B1.467 (7)
C10A—H102A0.9800C9B—H91B0.9900
C10A—H20C0.9800C9B—H92B0.9900
C11A—O12'A1.224 (19)C10B—H101B0.9800
C11A—O12A1.225 (7)C10B—H102B0.9800
C11A—O13'A1.329 (5)C10B—H103B0.9800
C11A—O13A1.353 (7)C11B—O12B1.209 (5)
O13A—C14A1.458 (7)C11B—O13B1.327 (5)
O13'A—C14'A1.470 (4)O13B—C14B1.464 (5)
C14A—C15A1.495 (12)C14B—C15B1.464 (6)
C14A—H141A0.9900C14B—H141B0.9900
C14A—H142A0.9900C14B—H142B0.9900
C14'A—C15'A1.471 (5)C15B—H151B0.9800
C14'A—H141'A0.9900C15B—H152B0.9800
C14'A—H142'A0.9900C15B—H153B0.9800
H1W1—Ow1—H2W1109.2C14A—C15A—H153A109.5
H1W2i—Ow2—H1W2107.0H151A—C15A—H153A109.5
N2A—N1A—C5A109.2 (3)H152A—C15A—H153A109.5
N2A—N1A—H1A125.4C14'A—C15'A—H151'A109.5
C5A—N1A—H1A125.4C14'A—C15'A—H152'A109.5
N1A—N2A—C3A107.1 (3)H151'A—C15'A—H152'A109.5
N1A—N2A—H2A126.5C14'A—C15'A—H153'A109.5
C3A—N2A—H2A126.5H151'A—C15'A—H153'A109.5
N2A—C3A—C4A110.1 (4)H152'A—C15'A—H153'A109.5
N2A—C3A—C6A123.4 (4)N2B—N1B—C5B109.5 (3)
C4A—C3A—C6A126.4 (4)N2B—N1B—H1B125.2
C3A—C4A—C5A104.9 (4)C5B—N1B—H1B125.2
C3A—C4A—H4A127.5N1B—N2B—C3B107.7 (3)
C5A—C4A—H4A127.5N1B—N2B—H2B126.2
N1A—C5A—C4A108.6 (4)C3B—N2B—H2B126.2
N1A—C5A—C11A122.4 (4)N2B—C3B—C4B109.5 (4)
C4A—C5A—C11A129.0 (4)N2B—C3B—C6B121.6 (4)
O7A—C6A—O8A125.9 (5)C4B—C3B—C6B128.8 (4)
O7A—C6A—C3A123.9 (5)C5B—C4B—C3B105.2 (4)
O8A—C6A—C3A110.2 (4)C5B—C4B—H4B127.4
C6A—O8A—C9A113.6 (4)C3B—C4B—H4B127.4
C10A—C9A—O8A106.5 (4)N1B—C5B—C4B108.1 (4)
C10A—C9A—H91A110.4N1B—C5B—C11B119.7 (4)
O8A—C9A—H91A110.4C4B—C5B—C11B132.2 (4)
C10A—C9A—H92A110.4O7B—C6B—O8B124.8 (4)
O8A—C9A—H92A110.4O7B—C6B—C3B123.9 (4)
H91A—C9A—H92A108.6O8B—C6B—C3B111.3 (4)
C9A—C10A—H101A109.5C6B—O8B—C9B116.8 (4)
C9A—C10A—H102A109.5O8B—C9B—C10B108.5 (5)
H101A—C10A—H102A109.5O8B—C9B—H91B110.0
C9A—C10A—H20C109.5C10B—C9B—H91B110.0
H101A—C10A—H20C109.5O8B—C9B—H92B110.0
H102A—C10A—H20C109.5C10B—C9B—H92B110.0
O12'A—C11A—O13'A122.9 (13)H91B—C9B—H92B108.4
O12A—C11A—O13'A120.2 (10)C9B—C10B—H101B109.5
O12A—C11A—O13A127.6 (5)C9B—C10B—H102B109.5
O12'A—C11A—C5A124.0 (9)H101B—C10B—H102B109.5
O12A—C11A—C5A120.8 (5)C9B—C10B—H103B109.5
O13'A—C11A—C5A111.7 (9)H101B—C10B—H103B109.5
O13A—C11A—C5A111.3 (4)H102B—C10B—H103B109.5
C11A—O13A—C14A119.7 (6)O12B—C11B—O13B123.7 (4)
C11A—O13'A—C14'A111.8 (14)O12B—C11B—C5B124.6 (4)
O13A—C14A—C15A109.0 (6)O13B—C11B—C5B111.7 (4)
O13A—C14A—H141A109.9C11B—O13B—C14B116.1 (3)
C15A—C14A—H141A109.9C15B—C14B—O13B108.8 (4)
O13A—C14A—H142A109.9C15B—C14B—H141B109.9
C15A—C14A—H142A109.9O13B—C14B—H141B109.9
H141A—C14A—H142A108.3C15B—C14B—H142B109.9
O13'A—C14'A—C15'A105.2 (19)O13B—C14B—H142B109.9
O13'A—C14'A—H141'A110.7H141B—C14B—H142B108.3
C15'A—C14'A—H141'A110.7C14B—C15B—H151B109.5
O13'A—C14'A—H142'A110.7C14B—C15B—H152B109.5
C15'A—C14'A—H142'A110.7H151B—C15B—H152B109.5
H141'A—C14'A—H142'A108.8C14B—C15B—H153B109.5
C14A—C15A—H151A109.5H151B—C15B—H153B109.5
C14A—C15A—H152A109.5H152B—C15B—H153B109.5
H151A—C15A—H152A109.5
C5A—N1A—N2A—C3A0.3 (5)C5A—C11A—O13'A—C14'A171.1 (14)
N1A—N2A—C3A—C4A0.7 (5)C11A—O13A—C14A—C15A112.5 (15)
N1A—N2A—C3A—C6A178.2 (4)C11A—O13'A—C14'A—C15'A146 (3)
N2A—C3A—C4A—C5A0.8 (5)C5B—N1B—N2B—C3B0.4 (4)
C6A—C3A—C4A—C5A178.2 (4)N1B—N2B—C3B—C4B0.4 (5)
N2A—N1A—C5A—C4A0.2 (5)N1B—N2B—C3B—C6B176.8 (4)
N2A—N1A—C5A—C11A179.7 (5)N2B—C3B—C4B—C5B0.2 (5)
C3A—C4A—C5A—N1A0.6 (5)C6B—C3B—C4B—C5B176.7 (4)
C3A—C4A—C5A—C11A179.3 (5)N2B—N1B—C5B—C4B0.3 (5)
N2A—C3A—C6A—O7A179.7 (5)N2B—N1B—C5B—C11B178.1 (4)
C4A—C3A—C6A—O7A2.6 (9)C3B—C4B—C5B—N1B0.0 (5)
N2A—C3A—C6A—O8A1.2 (7)C3B—C4B—C5B—C11B177.4 (4)
C4A—C3A—C6A—O8A175.9 (4)N2B—C3B—C6B—O7B174.9 (4)
O7A—C6A—O8A—C9A4.9 (8)C4B—C3B—C6B—O7B1.7 (8)
C3A—C6A—O8A—C9A173.5 (4)N2B—C3B—C6B—O8B4.7 (6)
C6A—O8A—C9A—C10A171.6 (5)C4B—C3B—C6B—O8B178.7 (4)
N1A—C5A—C11A—O12'A145.0 (12)O7B—C6B—O8B—C9B0.5 (7)
C4A—C5A—C11A—O12'A34.8 (14)C3B—C6B—O8B—C9B179.1 (4)
N1A—C5A—C11A—O12A172.6 (8)C6B—O8B—C9B—C10B163.1 (4)
C4A—C5A—C11A—O12A7.6 (11)N1B—C5B—C11B—O12B6.2 (7)
N1A—C5A—C11A—O13'A22.2 (13)C4B—C5B—C11B—O12B170.9 (5)
C4A—C5A—C11A—O13'A158.0 (11)N1B—C5B—C11B—O13B175.3 (4)
N1A—C5A—C11A—O13A2.5 (9)C4B—C5B—C11B—O13B7.5 (7)
C4A—C5A—C11A—O13A177.4 (7)O12B—C11B—O13B—C14B0.5 (7)
O12A—C11A—O13A—C14A4.2 (13)C5B—C11B—O13B—C14B178.0 (4)
C5A—C11A—O13A—C14A178.8 (6)C11B—O13B—C14B—C15B173.7 (5)
O12'A—C11A—O13'A—C14'A22 (2)
Symmetry code: (i) y, xy, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
Ow2—H1W2···N2B0.832.152.810 (3)136
N1B—H1B···N2A0.882.072.936 (5)166
N1A—H1A···Ow10.881.942.793 (3)164
Ow1—H1W1···Ow20.861.872.739 (7)180
N2A—H2A···N1B0.882.102.936 (5)158
N2B—H2B···Ow20.882.002.810 (3)153
Ow1—H2W1···N1A0.861.962.793 (3)161
 

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