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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o171.
Published online 2008 December 20. doi:  10.1107/S1600536808042608
PMCID: PMC2968082

Piperidinium bis­(2-oxidobenzoato-κ2 O 1,O 2)borate

Abstract

The asymmetric unit of the title compound, C5H12N+·C14H8BO6 or [C5H12N][BO4(C7H4O)2], contains two piperidinium cations and two bis­(salicylato)borate anions. The coordination geometries around the B atoms are distorted tetra­hedral. In the two mol­ecules, the aromatic rings are oriented at dihedral angles of 76.27 (3) and 83.86 (3)°. The rings containing B atoms have twist-boat conformations, while the two cations adopt chair conformations. In the crystal, the component species are linked by N—H(...)O hydrogen bonds. In the crystal structure, intra- and inter­molecular N—H(...)O hydrogen bonds link the mol­ecules.

Related literature

For general background, see: Barthel et al. (2000 [triangle]); Downard et al. (2002 [triangle]). For related structures, see: Han et al. (2007 [triangle]); Li & Liu (2006 [triangle]); Zhang et al. (2005 [triangle]). For ring puckering parameters, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o171-scheme1.jpg

Experimental

Crystal data

  • C5H12N+·C14H8BO6
  • M r = 369.17
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o171-efi1.jpg
  • a = 19.835 (7) Å
  • b = 16.247 (7) Å
  • c = 12.231 (5) Å
  • β = 111.624 (10)°
  • V = 3664 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 (2) K
  • 0.58 × 0.43 × 0.40 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1999 [triangle]) T min = 0.945, T max = 0.962
  • 9508 measured reflections
  • 3235 independent reflections
  • 1967 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.203
  • S = 1.04
  • 3235 reflections
  • 487 parameters
  • H-atom parameters constrained
  • Δρmax = 0.42 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042608/hk2548sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042608/hk2548Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

To date, alkali-metals bis(salicylato)borates have received the most attention (Zhang et al., 2005; Downard et al., 2002), since the lithium organoborates had been considered as the lithium battery electrolytes (Barthel et al., 2000). In contrast, studies of organic base bis(salicylato)- borates have been less extensive (Li & Liu, 2006; Han et al., 2007). We report herein the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound contains two [C5H12N]+ cations and two [BO4(C7H4O)2]- anions (Fig.1). In the anions, the sp3-hybridized B atoms are bonded to four oxygen atoms in distorted tetrahedral geometries (Table 1). Rings B (C2-C7), D (C9-C14) and F (C16-C21), H (C23-C28) are, of course, planar, and they are oriented at dihedral angles of B/D = 76.27 (3)° and D/F = 83.86 (3)°. Rings A (B1/O1/O3/C1-C3), C (B1/O4/O6/C8-C10) and E (B2/O7/O9/C15-C17), G (B2/O10/O12/C22-C24) are not planar, having total puckering amplitudes, QT, of 0.739 (2), 0.689 (3) Å and 0.724 (3), 0.859 (3) Å, respectively, twisted-boat conformations [[var phi] = -52.97 (4)° and θ = 105.16 (5)°; [var phi] = -51.39 (4)° and θ = 104.63 (3)°; [var phi] = -56.94 (4)° and θ = 109.52 (5)°; [var phi] = -55.15 (5)° and θ = 108.00 (5)°, respectively] (Cremer & Pople, 1975). Rings I (N1/C29-C33) and J (N2/C34-C38) adopt, of course, chair conformations, having total puckering amplitudes, QT, of 0.562 (3) and 0.562 (3) Å, respectively [[var phi] = -69.55 (3)° and θ = 178.57 (4)°; [var phi] = -132.85 (4)° and θ = 4.37 (4)°, respectively] (Cremer & Pople, 1975). The intramolecular N-H···O hydrogen bonds (Table 2 and Fig. 1) link the cations to the anions.

In the crystal structure, the intra- and intermolecular N-H···O hydrogen bonds (Table 2) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, a solution of boric acid (0.325 g) in distilled water (5 ml) was added to a stirred solution of salicylic acid (1.418 g) in an ethanol/water (1:1) solvent (10 ml). The reaction mixture was stirred at 353 K for 20 min, and then piperidinium (1 ml) was added slowly. After 4 h continued heating and stirring, the pH of the mixture had changed from 2 to 6, and the clear solution was then allowed to stand for 15 d at room temperature. The title compound was isolated as colorless transparent crystals. Elemental analysis calc.: C 61.80, N 3.79, H 5.47%; found: C 62.12, N 3.62, H 5.12%.

Refinement

H atoms were positioned geometrically, with N-H = 0.90 Å (for NH2) and C-H = 0.93 and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level. Hydrogen bonds are shown as dashed lines.
Fig. 2.
A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C5H12N+·C14H8BO6F(000) = 1552
Mr = 369.17Dx = 1.338 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1899 reflections
a = 19.835 (7) Åθ = 2.2–23.1°
b = 16.247 (7) ŵ = 0.10 mm1
c = 12.231 (5) ÅT = 298 K
β = 111.624 (10)°Clubbed, colorless
V = 3664 (3) Å30.58 × 0.43 × 0.40 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer3235 independent reflections
Radiation source: fine-focus sealed tube1967 reflections with I > 2σ(I)
graphiteRint = 0.053
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1999)h = −23→23
Tmin = 0.945, Tmax = 0.962k = −19→16
9508 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.203w = 1/[σ2(Fo2) + (0.1245P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3235 reflectionsΔρmax = 0.42 e Å3
487 parametersΔρmin = −0.23 e Å3
Primary atom site location: structure-invariant direct methods

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.2375 (3)0.3316 (3)0.5857 (5)0.0459 (13)
O20.1339 (3)0.3910 (3)0.5637 (5)0.0572 (15)
O30.3536 (3)0.3847 (3)0.7220 (5)0.0458 (13)
O40.3144 (3)0.2518 (3)0.7485 (5)0.0461 (13)
O50.2966 (4)0.1240 (3)0.7940 (6)0.0635 (16)
O60.3499 (3)0.2835 (3)0.5839 (5)0.0490 (13)
O70.0436 (3)0.2515 (3)0.0932 (4)0.0481 (13)
O80.0554 (3)0.3784 (3)0.1602 (5)0.0583 (15)
O90.0048 (3)0.2223 (3)−0.1159 (4)0.0498 (13)
O100.1147 (3)0.1677 (3)0.0174 (5)0.0461 (13)
O110.2152 (3)0.0991 (4)0.1091 (6)0.0630 (16)
O12−0.0013 (3)0.1207 (3)0.0170 (5)0.0455 (13)
N10.0823 (3)0.2848 (4)0.3669 (6)0.0476 (16)
H1A0.08340.31480.30570.057*
H1B0.10110.31570.43220.057*
N20.2593 (3)0.2086 (4)−0.0346 (6)0.0494 (16)
H2A0.26110.1741−0.09120.059*
H2B0.23790.18160.00810.059*
B10.3161 (4)0.3137 (5)0.6602 (7)0.0375 (19)
B20.0379 (5)0.1900 (5)0.0013 (8)0.041 (2)
C10.2001 (4)0.3872 (4)0.6166 (7)0.0429 (18)
C20.2406 (4)0.4427 (4)0.7122 (6)0.0365 (16)
C30.3163 (4)0.4403 (4)0.7615 (6)0.0407 (17)
C40.3549 (4)0.4981 (5)0.8441 (7)0.049 (2)
H40.40530.49780.87310.059*
C50.3183 (5)0.5560 (5)0.8832 (8)0.060 (2)
H50.34390.59420.94000.072*
C60.2431 (5)0.5571 (5)0.8373 (8)0.062 (2)
H60.21830.59590.86420.074*
C70.2053 (5)0.5024 (5)0.7539 (8)0.055 (2)
H70.15490.50450.72380.066*
C80.3096 (4)0.1710 (4)0.7260 (7)0.0429 (18)
C90.3228 (4)0.1448 (5)0.6222 (7)0.0452 (18)
C100.3428 (4)0.2031 (4)0.5546 (7)0.0417 (17)
C110.3556 (5)0.1784 (6)0.4551 (8)0.058 (2)
H110.36930.21650.41030.069*
C120.3480 (5)0.0977 (6)0.4244 (9)0.070 (3)
H120.35590.08160.35720.085*
C130.3292 (6)0.0393 (6)0.4874 (10)0.079 (3)
H130.3243−0.01540.46340.095*
C140.3173 (5)0.0624 (5)0.5885 (9)0.064 (2)
H140.30560.02280.63360.077*
C150.0430 (4)0.3318 (4)0.0751 (7)0.0418 (17)
C160.0305 (4)0.3602 (5)−0.0449 (7)0.0420 (17)
C170.0130 (4)0.3028 (5)−0.1354 (6)0.0435 (18)
C180.0028 (4)0.3290 (6)−0.2479 (7)0.058 (2)
H18−0.00730.2911−0.30880.070*
C190.0076 (5)0.4118 (6)−0.2696 (9)0.074 (3)
H190.00020.4294−0.34550.089*
C200.0233 (6)0.4689 (6)−0.1802 (9)0.078 (3)
H200.02560.5247−0.19550.094*
C210.0355 (5)0.4415 (5)−0.0671 (9)0.061 (2)
H210.04720.4792−0.00560.074*
C220.1505 (4)0.1094 (4)0.0904 (7)0.0451 (19)
C230.1087 (4)0.0581 (4)0.1416 (6)0.0384 (17)
C240.0343 (4)0.0664 (4)0.1038 (6)0.0411 (18)
C25−0.0054 (5)0.0182 (5)0.1517 (8)0.053 (2)
H25−0.05540.02460.12780.064*
C260.0304 (6)−0.0395 (5)0.2353 (8)0.067 (3)
H260.0041−0.07310.26650.080*
C270.1045 (5)−0.0483 (5)0.2735 (9)0.067 (3)
H270.1276−0.08740.33060.080*
C280.1445 (5)0.0001 (5)0.2280 (7)0.054 (2)
H280.1946−0.00560.25430.065*
C290.0057 (5)0.2642 (5)0.3479 (8)0.057 (2)
H29A−0.01620.23510.27390.069*
H29B−0.02160.31440.34360.069*
C300.0024 (5)0.2116 (6)0.4465 (9)0.070 (3)
H30A−0.04750.19620.43100.084*
H30B0.02010.24260.51930.084*
C310.0479 (6)0.1345 (6)0.4591 (10)0.078 (3)
H31A0.02710.10040.38960.094*
H31B0.04810.10300.52660.094*
C320.1256 (5)0.1579 (6)0.4749 (9)0.070 (3)
H32A0.14800.18660.54910.084*
H32B0.15330.10830.47760.084*
C330.1276 (5)0.2104 (6)0.3794 (8)0.060 (2)
H33A0.11030.17960.30630.073*
H33B0.17730.22670.39470.073*
C340.2141 (5)0.2807 (6)−0.0911 (9)0.068 (3)
H34A0.16470.2630−0.13380.082*
H34B0.23250.3053−0.14680.082*
C350.2150 (5)0.3438 (6)0.0000 (10)0.073 (3)
H35A0.18960.32190.04780.087*
H35B0.18940.3927−0.03940.087*
C360.2913 (7)0.3672 (7)0.0786 (12)0.090 (4)
H36A0.31550.39440.03260.109*
H36B0.28970.40500.13890.109*
C370.3326 (6)0.2910 (6)0.1350 (10)0.082 (3)
H37A0.30980.26580.18450.098*
H37B0.38180.30590.18430.098*
C380.3344 (5)0.2300 (6)0.0428 (9)0.068 (3)
H38A0.35990.2538−0.00380.082*
H38B0.36010.18070.08060.082*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.050 (3)0.037 (3)0.044 (3)0.001 (2)0.008 (2)−0.007 (2)
O20.044 (3)0.059 (3)0.055 (4)0.005 (2)0.002 (3)−0.013 (3)
O30.042 (3)0.033 (3)0.059 (4)−0.004 (2)0.015 (3)−0.008 (2)
O40.060 (3)0.042 (3)0.038 (3)0.006 (2)0.021 (3)0.005 (2)
O50.092 (4)0.048 (3)0.061 (4)−0.006 (3)0.042 (3)0.008 (3)
O60.065 (3)0.036 (3)0.056 (4)0.006 (2)0.033 (3)0.000 (2)
O70.074 (4)0.034 (3)0.033 (3)0.007 (2)0.016 (3)0.003 (2)
O80.085 (4)0.042 (3)0.047 (4)−0.003 (3)0.023 (3)−0.006 (3)
O90.066 (3)0.041 (3)0.032 (3)0.002 (2)0.005 (2)0.001 (2)
O100.052 (3)0.040 (3)0.050 (3)0.005 (2)0.024 (3)0.008 (2)
O110.054 (4)0.065 (4)0.075 (4)0.006 (3)0.029 (3)0.018 (3)
O120.050 (3)0.036 (3)0.046 (3)−0.003 (2)0.012 (3)0.004 (2)
N10.050 (4)0.058 (4)0.030 (3)−0.007 (3)0.009 (3)0.000 (3)
N20.045 (4)0.062 (4)0.041 (4)−0.004 (3)0.016 (3)−0.001 (3)
B10.048 (5)0.032 (4)0.034 (5)0.001 (3)0.017 (4)−0.004 (3)
B20.054 (5)0.033 (4)0.033 (5)0.001 (4)0.013 (4)−0.003 (4)
C10.046 (5)0.043 (4)0.036 (4)0.000 (3)0.010 (4)0.003 (3)
C20.042 (4)0.032 (4)0.031 (4)0.000 (3)0.008 (3)0.003 (3)
C30.046 (4)0.031 (4)0.040 (5)0.002 (3)0.009 (4)0.003 (3)
C40.049 (5)0.047 (4)0.041 (5)−0.006 (3)0.004 (4)−0.012 (4)
C50.079 (6)0.045 (5)0.044 (5)−0.002 (4)0.010 (4)−0.019 (4)
C60.064 (6)0.061 (5)0.055 (6)0.016 (4)0.015 (5)−0.016 (4)
C70.052 (5)0.050 (5)0.054 (5)0.005 (4)0.010 (4)−0.010 (4)
C80.045 (4)0.040 (4)0.043 (5)0.000 (3)0.016 (4)0.001 (4)
C90.050 (4)0.041 (4)0.045 (5)0.005 (3)0.017 (4)−0.005 (4)
C100.041 (4)0.042 (4)0.044 (5)0.005 (3)0.018 (3)−0.003 (4)
C110.060 (5)0.073 (6)0.052 (6)−0.002 (4)0.033 (5)−0.003 (5)
C120.073 (6)0.081 (7)0.060 (6)−0.002 (5)0.027 (5)−0.025 (5)
C130.091 (8)0.055 (6)0.095 (8)−0.006 (5)0.037 (7)−0.035 (6)
C140.072 (6)0.044 (5)0.074 (7)−0.006 (4)0.025 (5)−0.006 (4)
C150.052 (4)0.036 (4)0.038 (4)0.002 (3)0.018 (4)−0.003 (3)
C160.045 (4)0.040 (4)0.040 (4)0.000 (3)0.013 (3)0.003 (3)
C170.043 (4)0.054 (5)0.029 (4)0.005 (4)0.007 (3)0.007 (4)
C180.056 (5)0.083 (6)0.026 (4)−0.002 (4)0.005 (4)0.006 (4)
C190.091 (7)0.078 (7)0.047 (6)−0.010 (5)0.019 (5)0.026 (5)
C200.099 (8)0.061 (6)0.068 (7)−0.008 (5)0.023 (6)0.030 (6)
C210.079 (6)0.040 (5)0.063 (6)−0.008 (4)0.024 (5)0.004 (4)
C220.047 (5)0.043 (4)0.043 (5)0.002 (3)0.015 (4)−0.004 (3)
C230.046 (4)0.034 (4)0.038 (4)0.003 (3)0.018 (3)−0.001 (3)
C240.051 (5)0.033 (4)0.036 (4)−0.001 (3)0.012 (4)−0.004 (3)
C250.059 (5)0.052 (5)0.053 (5)−0.008 (4)0.024 (4)0.000 (4)
C260.096 (8)0.052 (5)0.059 (6)−0.007 (5)0.038 (6)0.013 (4)
C270.075 (6)0.059 (5)0.065 (6)0.019 (5)0.024 (5)0.031 (5)
C280.064 (6)0.055 (5)0.040 (5)0.013 (4)0.015 (4)0.008 (4)
C290.055 (5)0.070 (5)0.045 (5)0.011 (4)0.017 (4)−0.001 (4)
C300.057 (5)0.095 (7)0.058 (6)−0.010 (5)0.022 (5)−0.009 (5)
C310.092 (8)0.069 (6)0.070 (7)−0.012 (5)0.025 (6)0.013 (5)
C320.067 (6)0.061 (6)0.069 (7)0.003 (4)0.011 (5)−0.001 (5)
C330.051 (5)0.073 (6)0.049 (5)0.006 (4)0.008 (4)−0.013 (5)
C340.060 (5)0.079 (6)0.065 (6)0.003 (5)0.022 (5)0.022 (5)
C350.071 (6)0.065 (6)0.082 (7)0.000 (5)0.030 (5)−0.004 (5)
C360.093 (8)0.072 (7)0.118 (11)−0.017 (6)0.053 (8)−0.023 (7)
C370.066 (6)0.083 (7)0.079 (8)0.000 (5)0.007 (6)−0.036 (6)
C380.052 (5)0.075 (6)0.069 (7)−0.003 (4)0.011 (5)−0.010 (5)

Geometric parameters (Å, °)

O1—C11.310 (9)C15—C161.470 (11)
O1—B11.515 (10)C16—C211.359 (11)
O2—C11.233 (9)C16—C171.389 (10)
O3—C31.364 (8)C17—C181.383 (11)
O3—B11.429 (9)C18—C191.381 (13)
O4—C81.336 (8)C18—H180.9300
O4—B11.485 (10)C19—C201.378 (14)
O5—C81.224 (9)C19—H190.9300
O6—C101.347 (8)C20—C211.387 (13)
O6—B11.422 (10)C20—H200.9300
O7—C151.323 (8)C21—H210.9300
O7—B21.477 (10)C22—C231.469 (10)
O8—C151.236 (9)C23—C241.380 (10)
O9—C171.349 (9)C23—C281.399 (10)
O9—B21.439 (10)C24—C251.385 (11)
O10—C221.316 (9)C25—C261.375 (12)
O10—B21.505 (10)C25—H250.9300
O11—C221.229 (9)C26—C271.374 (13)
O12—C241.360 (9)C26—H260.9300
O12—B21.421 (10)C27—C281.372 (12)
N1—C291.489 (10)C27—H270.9300
N1—C331.480 (10)C28—H280.9300
N1—H1A0.9000C29—C301.499 (13)
N1—H1B0.9000C29—H29A0.9700
N2—C341.482 (11)C29—H29B0.9700
N2—C381.483 (11)C30—C311.518 (14)
N2—H2A0.9000C30—H30A0.9700
N2—H2B0.9000C30—H30B0.9700
C1—C21.461 (10)C31—C321.528 (14)
C2—C31.397 (10)C31—H31A0.9700
C2—C71.398 (10)C31—H31B0.9700
C3—C41.385 (10)C32—C331.458 (13)
C4—C51.377 (12)C32—H32A0.9700
C4—H40.9300C32—H32B0.9700
C5—C61.387 (13)C33—H33A0.9700
C5—H50.9300C33—H33B0.9700
C6—C71.352 (12)C34—C351.510 (14)
C6—H60.9300C34—H34A0.9700
C7—H70.9300C34—H34B0.9700
C8—C91.452 (11)C35—C361.512 (16)
C9—C141.393 (11)C35—H35A0.9700
C9—C101.407 (11)C35—H35B0.9700
C10—C111.392 (11)C36—C371.504 (16)
C11—C121.357 (12)C36—H36A0.9700
C11—H110.9300C36—H36B0.9700
C12—C131.359 (14)C37—C381.512 (14)
C12—H120.9300C37—H37A0.9700
C13—C141.393 (14)C37—H37B0.9700
C13—H130.9300C38—H38A0.9700
C14—H140.9300C38—H38B0.9700
C33—N1—C29112.2 (6)C18—C19—H19119.5
C33—N1—H1A109.2C19—C20—C21118.7 (8)
C29—N1—H1A109.2C19—C20—H20120.6
C33—N1—H1B109.2C21—C20—H20120.6
C29—N1—H1B109.2C16—C21—C20120.8 (9)
H1A—N1—H1B107.9C16—C21—H21119.6
C34—N2—C38113.8 (7)C20—C21—H21119.6
C34—N2—H2A108.8O11—C22—O10119.4 (7)
C38—N2—H2A108.8O11—C22—C23124.0 (7)
C34—N2—H2B108.8O10—C22—C23116.6 (6)
C38—N2—H2B108.8C24—C23—C28120.1 (7)
H2A—N2—H2B107.7C24—C23—C22120.3 (6)
C1—O1—B1121.7 (6)C28—C23—C22119.7 (7)
C3—O3—B1118.5 (6)O12—C24—C23120.6 (6)
C8—O4—B1122.3 (6)O12—C24—C25118.9 (7)
C10—O6—B1118.7 (6)C23—C24—C25120.5 (7)
C15—O7—B2123.1 (6)C26—C25—C24118.7 (8)
C17—O9—B2119.3 (6)C26—C25—H25120.6
C22—O10—B2122.0 (6)C24—C25—H25120.6
C24—O12—B2117.8 (6)C27—C26—C25121.3 (8)
O6—B1—O3110.3 (6)C27—C26—H26119.4
O6—B1—O4112.7 (6)C25—C26—H26119.4
O3—B1—O4108.0 (6)C28—C27—C26120.4 (8)
O6—B1—O1107.5 (6)C28—C27—H27119.8
O3—B1—O1112.5 (6)C26—C27—H27119.8
O4—B1—O1105.9 (6)C27—C28—C23119.0 (8)
O12—B2—O9110.7 (6)C27—C28—H28120.5
O12—B2—O7108.9 (7)C23—C28—H28120.5
O9—B2—O7113.0 (6)N1—C29—C30110.3 (7)
O12—B2—O10111.7 (6)N1—C29—H29A109.6
O9—B2—O10106.7 (6)C30—C29—H29A109.6
O7—B2—O10105.9 (6)N1—C29—H29B109.6
O2—C1—O1119.4 (7)C30—C29—H29B109.6
O2—C1—C2123.6 (7)H29A—C29—H29B108.1
O1—C1—C2116.9 (6)C29—C30—C31110.6 (8)
C3—C2—C7117.7 (7)C29—C30—H30A109.5
C3—C2—C1121.0 (6)C31—C30—H30A109.5
C7—C2—C1121.2 (7)C29—C30—H30B109.5
O3—C3—C4118.8 (7)C31—C30—H30B109.5
O3—C3—C2120.2 (6)H30A—C30—H30B108.1
C4—C3—C2120.8 (7)C30—C31—C32110.0 (8)
C5—C4—C3119.8 (8)C30—C31—H31A109.7
C5—C4—H4120.1C32—C31—H31A109.7
C3—C4—H4120.1C30—C31—H31B109.7
C4—C5—C6119.6 (7)C32—C31—H31B109.7
C4—C5—H5120.2H31A—C31—H31B108.2
C6—C5—H5120.2C33—C32—C31111.6 (8)
C7—C6—C5120.7 (8)C33—C32—H32A109.3
C7—C6—H6119.6C31—C32—H32A109.3
C5—C6—H6119.6C33—C32—H32B109.3
C6—C7—C2121.2 (8)C31—C32—H32B109.3
C6—C7—H7119.4H32A—C32—H32B108.0
C2—C7—H7119.4C32—C33—N1111.4 (7)
O5—C8—O4119.3 (7)C32—C33—H33A109.3
O5—C8—C9124.2 (7)N1—C33—H33A109.3
O4—C8—C9116.5 (7)C32—C33—H33B109.3
C14—C9—C10118.9 (7)N1—C33—H33B109.3
C14—C9—C8121.4 (8)H33A—C33—H33B108.0
C10—C9—C8119.8 (6)N2—C34—C35110.7 (8)
O6—C10—C11118.5 (7)N2—C34—H34A109.5
O6—C10—C9121.4 (7)C35—C34—H34A109.5
C11—C10—C9120.1 (7)N2—C34—H34B109.5
C12—C11—C10118.9 (9)C35—C34—H34B109.5
C12—C11—H11120.6H34A—C34—H34B108.1
C10—C11—H11120.6C34—C35—C36112.1 (8)
C11—C12—C13123.0 (9)C34—C35—H35A109.2
C11—C12—H12118.5C36—C35—H35A109.2
C13—C12—H12118.5C34—C35—H35B109.2
C12—C13—C14119.1 (8)C36—C35—H35B109.2
C12—C13—H13120.4H35A—C35—H35B107.9
C14—C13—H13120.4C37—C36—C35109.5 (8)
C9—C14—C13120.0 (9)C37—C36—H36A109.8
C9—C14—H14120.0C35—C36—H36A109.8
C13—C14—H14120.0C37—C36—H36B109.8
O8—C15—O7118.4 (7)C35—C36—H36B109.8
O8—C15—C16123.8 (7)H36A—C36—H36B108.2
O7—C15—C16117.7 (6)C36—C37—C38110.9 (9)
C21—C16—C17120.6 (7)C36—C37—H37A109.5
C21—C16—C15120.4 (7)C38—C37—H37A109.5
C17—C16—C15119.0 (6)C36—C37—H37B109.5
O9—C17—C18119.5 (7)C38—C37—H37B109.5
O9—C17—C16121.4 (6)H37A—C37—H37B108.1
C18—C17—C16119.1 (7)N2—C38—C37109.6 (7)
C19—C18—C17119.8 (9)N2—C38—H38A109.7
C19—C18—H18120.1C37—C38—H38A109.7
C17—C18—H18120.1N2—C38—H38B109.7
C20—C19—C18120.9 (8)C37—C38—H38B109.7
C20—C19—H19119.5H38A—C38—H38B108.2
C10—O6—B1—O3154.0 (6)C9—C10—C11—C120.6 (12)
C10—O6—B1—O433.3 (9)C10—C11—C12—C13−0.9 (14)
C10—O6—B1—O1−83.0 (8)C11—C12—C13—C14−0.2 (16)
C3—O3—B1—O6154.5 (6)C10—C9—C14—C13−2.0 (13)
C3—O3—B1—O4−82.0 (7)C8—C9—C14—C13179.0 (9)
C3—O3—B1—O134.5 (9)C12—C13—C14—C91.7 (15)
C8—O4—B1—O6−31.5 (9)B2—O7—C15—O8−172.8 (7)
C8—O4—B1—O3−153.5 (6)B2—O7—C15—C164.7 (10)
C8—O4—B1—O185.8 (7)O8—C15—C16—C213.1 (11)
C1—O1—B1—O6−153.1 (6)O7—C15—C16—C21−174.3 (7)
C1—O1—B1—O3−31.6 (9)O8—C15—C16—C17−176.4 (7)
C1—O1—B1—O486.2 (7)O7—C15—C16—C176.3 (10)
C24—O12—B2—O9157.6 (6)B2—O9—C17—C18159.2 (7)
C24—O12—B2—O7−77.7 (7)B2—O9—C17—C16−21.7 (11)
C24—O12—B2—O1038.9 (9)C21—C16—C17—O9−177.1 (7)
C17—O9—B2—O12152.9 (6)C15—C16—C17—O92.3 (11)
C17—O9—B2—O730.4 (10)C21—C16—C17—C182.0 (11)
C17—O9—B2—O10−85.5 (8)C15—C16—C17—C18−178.6 (7)
C15—O7—B2—O12−145.8 (6)O9—C17—C18—C19176.8 (8)
C15—O7—B2—O9−22.4 (10)C16—C17—C18—C19−2.3 (12)
C15—O7—B2—O1094.0 (7)C17—C18—C19—C200.7 (14)
C22—O10—B2—O12−31.6 (9)C18—C19—C20—C211.2 (16)
C22—O10—B2—O9−152.6 (6)C17—C16—C21—C20−0.1 (13)
C22—O10—B2—O786.8 (8)C15—C16—C21—C20−179.5 (9)
B1—O1—C1—O2−168.9 (7)C19—C20—C21—C16−1.5 (15)
B1—O1—C1—C212.2 (9)B2—O10—C22—O11−172.8 (7)
O2—C1—C2—C3−174.1 (7)B2—O10—C22—C239.4 (9)
O1—C1—C2—C34.8 (10)O11—C22—C23—C24−171.1 (7)
O2—C1—C2—C73.2 (11)O10—C22—C23—C246.6 (10)
O1—C1—C2—C7−178.0 (7)O11—C22—C23—C288.2 (11)
B1—O3—C3—C4164.9 (7)O10—C22—C23—C28−174.1 (7)
B1—O3—C3—C2−20.2 (10)B2—O12—C24—C23−25.9 (9)
C7—C2—C3—O3−178.4 (7)B2—O12—C24—C25155.6 (7)
C1—C2—C3—O3−1.0 (10)C28—C23—C24—O12−177.8 (6)
C7—C2—C3—C4−3.6 (10)C22—C23—C24—O121.5 (10)
C1—C2—C3—C4173.8 (7)C28—C23—C24—C250.7 (11)
O3—C3—C4—C5178.5 (7)C22—C23—C24—C25179.9 (7)
C2—C3—C4—C53.6 (12)O12—C24—C25—C26176.8 (7)
C3—C4—C5—C6−1.5 (13)C23—C24—C25—C26−1.7 (11)
C4—C5—C6—C7−0.6 (14)C24—C25—C26—C271.6 (13)
C5—C6—C7—C20.6 (14)C25—C26—C27—C28−0.6 (14)
C3—C2—C7—C61.5 (12)C26—C27—C28—C23−0.5 (14)
C1—C2—C7—C6−175.9 (8)C24—C23—C28—C270.4 (12)
B1—O4—C8—O5−168.2 (7)C22—C23—C28—C27−178.9 (8)
B1—O4—C8—C913.7 (10)C33—N1—C29—C3056.8 (9)
O5—C8—C9—C143.8 (12)N1—C29—C30—C31−56.3 (10)
O4—C8—C9—C14−178.2 (7)C29—C30—C31—C3255.3 (11)
O5—C8—C9—C10−175.1 (8)C30—C31—C32—C33−55.2 (12)
O4—C8—C9—C102.9 (10)C31—C32—C33—N155.6 (10)
B1—O6—C10—C11160.6 (7)C29—N1—C33—C32−56.7 (9)
B1—O6—C10—C9−19.4 (10)C38—N2—C34—C35−53.5 (10)
C14—C9—C10—O6−179.1 (7)N2—C34—C35—C3652.9 (11)
C8—C9—C10—O6−0.1 (11)C34—C35—C36—C37−55.8 (13)
C14—C9—C10—C110.9 (12)C35—C36—C37—C3858.2 (12)
C8—C9—C10—C11179.9 (7)C34—N2—C38—C3755.9 (11)
O6—C10—C11—C12−179.4 (7)C36—C37—C38—N2−57.8 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O80.901.952.828 (9)163
N1—H1B···O20.901.932.829 (9)174
N2—H2A···O5i0.901.962.824 (10)159
N2—H2B···O110.901.982.855 (9)163

Symmetry codes: (i) x, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2548).

References

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