Chiral anionic layers in tartramide spiro­borate salts and variable solvation for [NR₄][B(TarNH₂)₂] (R = Et, Pr or Bu)

The spiro­borate anion, namely, 2,3,7,8-tetra­carboxamido-1,4,6,9-tetra­oxa-5λ⁴-bora­spiro­[4.4]nonane, [B(TarNH₂)₂]⁻, derived from the diol L-tartramide TarNH₂, [CH(O)(CONH₂)]₂, shows a novel self-assembly into two-dimensional (2D) layer structures in its salts with alkyl­ammonium cations, [NR₄]⁺ (R = Et, Pr and Bu), and sparteinium, [HSpa]⁺, in which the cations and anions are segregated. The structures of four such salts are reported, namely, the tetra­propyl­aza­nium salt, C₁₂H₂₈N⁺·C₈H₁₂BN₄O₈⁻, the tetra­ethyl­aza­nium salt hydrate, C₈H₂₀N⁺·C₈H₁₂BN₄O₈⁻·6.375H₂O, the tetra­butyl­aza­nium salt as the ethanol monosolvate hemihydrate, C₁₆H₃₆N⁺·C₈H₁₂BN₄O₈⁻·C₂H₅OH·0.5H₂O, and the sparteinium (7-aza-15-azonia­tetra­cyclo­[7.7.1.0^2,7.0^10,15]hepta­deca­ne) salt as the ethanol monosolvate, C₁₅H₂₇N₂⁺·C₈H₁₂BN₄O₈⁻·C₂H₅OH. The 2D anion layers have preserved inter­molecular hydrogen bonding between the amide groups and a typical metric repeat of around 10 × 15 Å. The constraint of matching the inter­facial area organizes the cations into quite different solvated arrangements, i.e. the [NEt₄] salt is highly hydrated with around 6.5H₂O per cation, the [NPr₄] salt apparently has a good metric match to the anion layer and is unsolvated, whilst the [NBu₄] salt is inter­mediate and has EtOH and H₂O in its cation layer, which is similar to the arrangement for the chiral [HSpa]⁺ cation. This family of salts shows highly organized chiral space and offers potential for the resolution of both chiral cations and neutral chiral solvent mol­ecules.

Computing details

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for aris38cult, aris36a, aris52cult; olex2.solve (Bourhis et al., 2015) for aris40cult. For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Tetrapropylazanium 2,3,7,8-tetracarboxamido-1,4,6,9-tetraoxa-5λ⁴-boraspiro[4.4]nonane (aris38cult)

Crystal data

C12H28N^+·C8H12BN4O8^−	F(000) = 528
Mr = 489.38	Dx = 1.316 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 9.72506 (16) Å	Cell parameters from 5190 reflections
b = 13.58223 (15) Å	θ = 4.7–75.3°
c = 10.40990 (17) Å	µ = 0.84 mm^−1
β = 116.071 (2)°	T = 100 K
V = 1235.12 (4) Å^3	Block, colourless
Z = 2	0.15 × 0.15 × 0.1 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	4411 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	4275 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.018
Detector resolution: 10.3577 pixels mm^-1	θmax = 67.5°, θmin = 4.7°
ω scans	h = −8→11
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −16→16
Tmin = 0.959, Tmax = 1.000	l = −12→11
6966 measured reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0336P)^2 + 0.0425P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.024	(Δ/σ)max < 0.001
wR(F^2) = 0.060	Δρmax = 0.18 e Å^−3
S = 1.03	Δρmin = −0.14 e Å^−3
4411 reflections	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
344 parameters	Extinction coefficient: 0.0025 (4)
1 restraint	Absolute structure: Flack x determined using 1970 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (7)
Hydrogen site location: mixed

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.16213 (17)	0.64682 (10)	0.97318 (15)	0.0236 (3)
O2	0.23534 (14)	0.40304 (10)	0.88244 (13)	0.0151 (3)
O3	0.00346 (13)	0.37350 (9)	0.89188 (13)	0.0152 (3)
O4	0.25751 (15)	0.41956 (10)	1.26069 (14)	0.0188 (3)
O5	−0.16438 (16)	0.09863 (10)	0.52559 (14)	0.0204 (3)
O6	0.11736 (15)	0.24071 (10)	0.81016 (13)	0.0176 (3)
O7	0.00695 (14)	0.37425 (9)	0.65774 (13)	0.0161 (3)
O8	0.10528 (17)	0.22923 (10)	0.42145 (14)	0.0209 (3)
N1	0.1103 (2)	0.57782 (13)	0.75862 (18)	0.0202 (3)
H1A	0.101 (3)	0.526 (2)	0.717 (3)	0.016 (6)*
H1B	0.062 (3)	0.631 (2)	0.708 (3)	0.028 (7)*
N4	0.09812 (19)	0.29164 (13)	1.15358 (18)	0.0176 (3)
H4A	0.024 (3)	0.2698 (17)	1.075 (3)	0.015 (5)*
H4B	0.117 (3)	0.265 (2)	1.236 (3)	0.028 (7)*
N5	−0.1390 (2)	0.13354 (14)	0.74753 (19)	0.0221 (4)
H5A	−0.092 (3)	0.163 (2)	0.823 (3)	0.031 (7)*
H5B	−0.209 (3)	0.091 (2)	0.741 (3)	0.027 (7)*
N8	0.15178 (18)	0.38904 (12)	0.48400 (16)	0.0165 (3)
H8A	0.129 (3)	0.442 (2)	0.521 (3)	0.023 (6)*
H8B	0.191 (3)	0.398 (2)	0.428 (3)	0.023 (6)*
C1	0.1612 (2)	0.57565 (14)	0.8992 (2)	0.0153 (4)
C2	0.2184 (2)	0.47527 (13)	0.97068 (19)	0.0141 (4)
H2	0.3167	0.4836	1.0591	0.017*
C3	0.09440 (18)	0.43293 (13)	1.00949 (19)	0.0136 (3)
H3	0.0300	0.4887	1.0148	0.016*
C4	0.15928 (19)	0.37875 (14)	1.15232 (19)	0.0150 (4)
C5	−0.0969 (2)	0.14016 (13)	0.64216 (19)	0.0153 (4)
C6	0.0434 (2)	0.20272 (13)	0.67026 (19)	0.0147 (4)
H6	0.1181	0.1624	0.6507	0.018*
C7	−0.0038 (2)	0.29373 (14)	0.56984 (18)	0.0148 (3)
H7	−0.1135	0.2858	0.4995	0.018*
C8	0.0917 (2)	0.30217 (14)	0.48663 (18)	0.0149 (3)
B1	0.0917 (2)	0.34686 (15)	0.8112 (2)	0.0149 (4)
N10	0.59976 (17)	0.49998 (12)	0.80520 (16)	0.0157 (3)
C11	0.72871 (19)	0.49852 (15)	0.95519 (19)	0.0165 (4)
H11A	0.7959	0.4418	0.9631	0.020*
H11B	0.7903	0.5591	0.9690	0.020*
C12	0.6813 (2)	0.49182 (16)	1.0763 (2)	0.0203 (4)
H12A	0.5915	0.4479	1.0485	0.024*
H12B	0.6532	0.5578	1.0974	0.024*
C13	0.8163 (2)	0.45089 (16)	1.2077 (2)	0.0214 (4)
H13A	0.8344	0.3823	1.1901	0.032*
H13B	0.7933	0.4540	1.2903	0.032*
H13C	0.9079	0.4901	1.2271	0.032*
C14	0.5064 (2)	0.40579 (15)	0.7749 (2)	0.0182 (4)
H14A	0.4483	0.4066	0.8326	0.022*
H14B	0.4309	0.4060	0.6729	0.022*
C15	0.5960 (2)	0.31063 (15)	0.8051 (2)	0.0249 (4)
H15A	0.6658	0.3058	0.9084	0.030*
H15B	0.6585	0.3092	0.7514	0.030*
C16	0.4848 (3)	0.22450 (16)	0.7598 (3)	0.0343 (5)
H16A	0.4233	0.2259	0.6558	0.051*
H16B	0.4172	0.2296	0.8069	0.051*
H16C	0.5421	0.1626	0.7875	0.051*
C17	0.4903 (2)	0.58449 (14)	0.7864 (2)	0.0184 (4)
H17A	0.4058	0.5812	0.6885	0.022*
H17B	0.4450	0.5750	0.8541	0.022*
C18	0.5605 (2)	0.68664 (15)	0.8096 (2)	0.0253 (4)
H18A	0.5981	0.7001	0.7370	0.030*
H18B	0.6485	0.6906	0.9054	0.030*
C19	0.4399 (3)	0.76258 (17)	0.7973 (3)	0.0355 (5)
H19A	0.3526	0.7577	0.7027	0.053*
H19B	0.4841	0.8288	0.8100	0.053*
H19C	0.4055	0.7501	0.8713	0.053*
C20	0.6754 (2)	0.50960 (14)	0.7049 (2)	0.0179 (4)
H20A	0.7362	0.5711	0.7287	0.022*
H20B	0.7476	0.4541	0.7234	0.022*
C21	0.5672 (2)	0.51091 (19)	0.5468 (2)	0.0296 (5)
H21A	0.5034	0.5711	0.5232	0.036*
H21B	0.4984	0.4530	0.5222	0.036*
C22	0.6596 (2)	0.50867 (17)	0.4614 (2)	0.0267 (4)
H22A	0.5900	0.5067	0.3590	0.040*
H22B	0.7250	0.4500	0.4874	0.040*
H22C	0.7236	0.5678	0.4825	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0350 (8)	0.0157 (7)	0.0193 (7)	0.0015 (6)	0.0114 (6)	−0.0021 (5)
O2	0.0160 (6)	0.0152 (6)	0.0158 (6)	0.0003 (5)	0.0087 (5)	−0.0020 (5)
O3	0.0143 (6)	0.0183 (6)	0.0124 (6)	−0.0022 (5)	0.0052 (5)	−0.0013 (5)
O4	0.0200 (6)	0.0225 (7)	0.0131 (6)	−0.0030 (5)	0.0065 (5)	−0.0008 (5)
O5	0.0265 (7)	0.0152 (6)	0.0165 (6)	−0.0038 (5)	0.0067 (6)	−0.0002 (5)
O6	0.0248 (7)	0.0130 (6)	0.0106 (6)	0.0012 (5)	0.0039 (5)	−0.0002 (5)
O7	0.0224 (6)	0.0126 (6)	0.0120 (6)	0.0028 (5)	0.0063 (5)	0.0006 (5)
O8	0.0336 (7)	0.0157 (6)	0.0164 (6)	−0.0025 (6)	0.0138 (6)	−0.0016 (5)
N1	0.0304 (9)	0.0135 (8)	0.0169 (8)	0.0025 (7)	0.0106 (7)	0.0006 (7)
N4	0.0216 (8)	0.0172 (8)	0.0139 (8)	−0.0014 (7)	0.0078 (6)	0.0002 (7)
N5	0.0253 (9)	0.0246 (9)	0.0202 (9)	−0.0023 (7)	0.0135 (7)	0.0011 (7)
N8	0.0213 (8)	0.0150 (8)	0.0137 (7)	−0.0014 (6)	0.0081 (6)	0.0005 (6)
C1	0.0159 (8)	0.0139 (8)	0.0171 (9)	−0.0027 (7)	0.0080 (7)	−0.0010 (7)
C2	0.0148 (8)	0.0144 (9)	0.0140 (8)	0.0003 (7)	0.0070 (7)	−0.0009 (6)
C3	0.0132 (8)	0.0140 (8)	0.0140 (9)	−0.0002 (7)	0.0063 (7)	−0.0014 (7)
C4	0.0147 (8)	0.0179 (9)	0.0152 (8)	0.0032 (7)	0.0091 (7)	−0.0010 (7)
C5	0.0198 (9)	0.0102 (8)	0.0153 (9)	0.0041 (7)	0.0072 (7)	0.0030 (7)
C6	0.0188 (9)	0.0128 (8)	0.0118 (8)	0.0011 (7)	0.0061 (7)	0.0005 (6)
C7	0.0184 (8)	0.0121 (8)	0.0127 (8)	0.0000 (7)	0.0058 (7)	0.0002 (7)
C8	0.0170 (8)	0.0143 (8)	0.0092 (7)	0.0007 (7)	0.0019 (6)	0.0016 (7)
B1	0.0176 (10)	0.0141 (10)	0.0119 (9)	0.0014 (8)	0.0055 (8)	0.0006 (7)
N10	0.0140 (7)	0.0165 (7)	0.0167 (7)	0.0002 (6)	0.0069 (6)	−0.0011 (6)
C11	0.0123 (8)	0.0180 (8)	0.0177 (9)	0.0001 (7)	0.0051 (7)	−0.0001 (7)
C12	0.0192 (9)	0.0235 (9)	0.0196 (9)	0.0028 (8)	0.0097 (7)	−0.0004 (8)
C13	0.0223 (9)	0.0245 (10)	0.0169 (9)	0.0006 (8)	0.0080 (8)	−0.0008 (8)
C14	0.0153 (8)	0.0180 (9)	0.0204 (9)	−0.0029 (7)	0.0070 (7)	−0.0011 (7)
C15	0.0206 (9)	0.0183 (10)	0.0341 (11)	−0.0001 (8)	0.0104 (9)	0.0009 (8)
C16	0.0305 (11)	0.0189 (11)	0.0462 (14)	−0.0034 (9)	0.0101 (10)	−0.0026 (10)
C17	0.0137 (8)	0.0196 (9)	0.0205 (9)	0.0038 (7)	0.0064 (7)	−0.0003 (8)
C18	0.0229 (10)	0.0187 (10)	0.0318 (11)	0.0013 (8)	0.0098 (8)	−0.0010 (8)
C19	0.0328 (11)	0.0220 (11)	0.0457 (14)	0.0075 (9)	0.0118 (10)	−0.0018 (10)
C20	0.0163 (8)	0.0199 (9)	0.0194 (9)	0.0017 (7)	0.0096 (7)	0.0008 (7)
C21	0.0220 (10)	0.0475 (15)	0.0192 (10)	0.0035 (9)	0.0089 (8)	0.0008 (9)
C22	0.0325 (11)	0.0305 (11)	0.0209 (9)	0.0075 (9)	0.0152 (8)	0.0051 (8)

Geometric parameters (Å, º)

O1—C1	1.234 (2)	N10—C20	1.524 (2)
O2—C2	1.402 (2)	C11—H11A	0.9900
O2—B1	1.474 (2)	C11—H11B	0.9900
O3—C3	1.407 (2)	C11—C12	1.523 (3)
O3—B1	1.486 (2)	C12—H12A	0.9900
O4—C4	1.243 (2)	C12—H12B	0.9900
O5—C5	1.234 (2)	C12—C13	1.525 (3)
O6—C6	1.408 (2)	C13—H13A	0.9800
O6—B1	1.464 (2)	C13—H13B	0.9800
O7—C7	1.400 (2)	C13—H13C	0.9800
O7—B1	1.487 (2)	C14—H14A	0.9900
O8—C8	1.240 (2)	C14—H14B	0.9900
N1—H1A	0.81 (3)	C14—C15	1.513 (3)
N1—H1B	0.89 (3)	C15—H15A	0.9900
N1—C1	1.323 (3)	C15—H15B	0.9900
N4—H4A	0.87 (3)	C15—C16	1.521 (3)
N4—H4B	0.87 (3)	C16—H16A	0.9800
N4—C4	1.327 (3)	C16—H16B	0.9800
N5—H5A	0.82 (3)	C16—H16C	0.9800
N5—H5B	0.87 (3)	C17—H17A	0.9900
N5—C5	1.331 (3)	C17—H17B	0.9900
N8—H8A	0.89 (3)	C17—C18	1.518 (3)
N8—H8B	0.84 (3)	C18—H18A	0.9900
N8—C8	1.322 (3)	C18—H18B	0.9900
C1—C2	1.536 (2)	C18—C19	1.525 (3)
C2—H2	1.0000	C19—H19A	0.9800
C2—C3	1.542 (2)	C19—H19B	0.9800
C3—H3	1.0000	C19—H19C	0.9800
C3—C4	1.525 (2)	C20—H20A	0.9900
C5—C6	1.523 (3)	C20—H20B	0.9900
C6—H6	1.0000	C20—C21	1.515 (3)
C6—C7	1.552 (2)	C21—H21A	0.9900
C7—H7	1.0000	C21—H21B	0.9900
C7—C8	1.527 (2)	C21—C22	1.518 (3)
N10—C11	1.513 (2)	C22—H22A	0.9800
N10—C14	1.519 (2)	C22—H22B	0.9800
N10—C17	1.519 (2)	C22—H22C	0.9800
C2—O2—B1	109.51 (13)	C12—C11—H11A	108.3
C3—O3—B1	109.47 (13)	C12—C11—H11B	108.3
C6—O6—B1	110.92 (14)	C11—C12—H12A	110.1
C7—O7—B1	110.69 (13)	C11—C12—H12B	110.1
H1A—N1—H1B	119 (2)	C11—C12—C13	108.05 (15)
C1—N1—H1A	117.7 (17)	H12A—C12—H12B	108.4
C1—N1—H1B	121.0 (17)	C13—C12—H12A	110.1
H4A—N4—H4B	121 (2)	C13—C12—H12B	110.1
C4—N4—H4A	119.2 (15)	C12—C13—H13A	109.5
C4—N4—H4B	118.3 (18)	C12—C13—H13B	109.5
H5A—N5—H5B	119 (3)	C12—C13—H13C	109.5
C5—N5—H5A	120.8 (19)	H13A—C13—H13B	109.5
C5—N5—H5B	119.6 (18)	H13A—C13—H13C	109.5
H8A—N8—H8B	117 (2)	H13B—C13—H13C	109.5
C8—N8—H8A	121.5 (16)	N10—C14—H14A	108.3
C8—N8—H8B	118.8 (19)	N10—C14—H14B	108.3
O1—C1—N1	124.74 (18)	H14A—C14—H14B	107.4
O1—C1—C2	119.41 (16)	C15—C14—N10	116.05 (14)
N1—C1—C2	115.84 (16)	C15—C14—H14A	108.3
O2—C2—C1	115.17 (15)	C15—C14—H14B	108.3
O2—C2—H2	110.0	C14—C15—H15A	109.9
O2—C2—C3	103.95 (13)	C14—C15—H15B	109.9
C1—C2—H2	110.0	C14—C15—C16	109.05 (17)
C1—C2—C3	107.45 (14)	H15A—C15—H15B	108.3
C3—C2—H2	110.0	C16—C15—H15A	109.9
O3—C3—C2	104.53 (13)	C16—C15—H15B	109.9
O3—C3—H3	108.2	C15—C16—H16A	109.5
O3—C3—C4	113.82 (14)	C15—C16—H16B	109.5
C2—C3—H3	108.2	C15—C16—H16C	109.5
C4—C3—C2	113.54 (14)	H16A—C16—H16B	109.5
C4—C3—H3	108.2	H16A—C16—H16C	109.5
O4—C4—N4	123.89 (18)	H16B—C16—H16C	109.5
O4—C4—C3	119.56 (16)	N10—C17—H17A	108.4
N4—C4—C3	116.40 (16)	N10—C17—H17B	108.4
O5—C5—N5	123.82 (18)	H17A—C17—H17B	107.5
O5—C5—C6	119.23 (16)	C18—C17—N10	115.41 (15)
N5—C5—C6	116.95 (17)	C18—C17—H17A	108.4
O6—C6—C5	114.22 (15)	C18—C17—H17B	108.4
O6—C6—H6	109.0	C17—C18—H18A	109.8
O6—C6—C7	105.66 (14)	C17—C18—H18B	109.8
C5—C6—H6	109.0	C17—C18—C19	109.21 (18)
C5—C6—C7	109.89 (14)	H18A—C18—H18B	108.3
C7—C6—H6	109.0	C19—C18—H18A	109.8
O7—C7—C6	105.48 (13)	C19—C18—H18B	109.8
O7—C7—H7	108.2	C18—C19—H19A	109.5
O7—C7—C8	115.02 (15)	C18—C19—H19B	109.5
C6—C7—H7	108.2	C18—C19—H19C	109.5
C8—C7—C6	111.61 (14)	H19A—C19—H19B	109.5
C8—C7—H7	108.2	H19A—C19—H19C	109.5
O8—C8—N8	123.20 (17)	H19B—C19—H19C	109.5
O8—C8—C7	119.18 (16)	N10—C20—H20A	108.4
N8—C8—C7	117.57 (16)	N10—C20—H20B	108.4
O2—B1—O3	104.14 (14)	H20A—C20—H20B	107.5
O2—B1—O7	111.49 (15)	C21—C20—N10	115.56 (15)
O3—B1—O7	111.17 (15)	C21—C20—H20A	108.4
O6—B1—O2	112.74 (15)	C21—C20—H20B	108.4
O6—B1—O3	112.74 (15)	C20—C21—H21A	109.8
O6—B1—O7	104.75 (14)	C20—C21—H21B	109.8
C11—N10—C14	110.60 (15)	C20—C21—C22	109.19 (16)
C11—N10—C17	111.03 (14)	H21A—C21—H21B	108.3
C11—N10—C20	106.11 (13)	C22—C21—H21A	109.8
C14—N10—C20	110.73 (14)	C22—C21—H21B	109.8
C17—N10—C14	106.77 (13)	C21—C22—H22A	109.5
C17—N10—C20	111.66 (14)	C21—C22—H22B	109.5
N10—C11—H11A	108.3	C21—C22—H22C	109.5
N10—C11—H11B	108.3	H22A—C22—H22B	109.5
N10—C11—C12	116.08 (14)	H22A—C22—H22C	109.5
H11A—C11—H11B	107.4	H22B—C22—H22C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.81 (3)	2.34 (2)	2.720 (2)	110 (2)
N1—H1A···O7	0.81 (3)	2.23 (3)	2.972 (2)	153 (2)
N1—H1B···O8^i	0.89 (3)	2.08 (3)	2.947 (2)	163 (2)
N4—H4A···O3	0.87 (3)	2.31 (2)	2.702 (2)	107.4 (18)
N4—H4B···O8^ii	0.87 (3)	2.04 (3)	2.886 (2)	162 (2)
N5—H5A···O6	0.82 (3)	2.35 (3)	2.707 (2)	107 (2)
N8—H8A···O7	0.89 (3)	2.41 (3)	2.745 (2)	102.7 (19)
N8—H8B···O4^iii	0.84 (3)	2.12 (3)	2.955 (2)	171 (2)

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) x, y, z+1; (iii) x, y, z−1.

Tetraethylazanium 2,3,7,8-tetracarboxamido-1,4,6,9-tetraoxa-5λ⁴-boraspiro[4.4]nonane 6.375-hydrate (aris40cult)

Crystal data

C8H20N^+·C8H12BN4O8^−·6.375H2O	Dx = 1.291 Mg m^−3
Mr = 548.13	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 9103 reflections
a = 10.40272 (13) Å	θ = 4.9–75.2°
b = 17.5277 (3) Å	µ = 0.96 mm^−1
c = 30.9259 (4) Å	T = 100 K
V = 5638.90 (13) Å^3	Plate, colourless
Z = 8	0.2 × 0.2 × 0.05 mm
F(000) = 2366

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	11082 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	10345 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
Detector resolution: 10.3577 pixels mm^-1	θmax = 75.7°, θmin = 4.5°
ω scans	h = −12→8
Absorption correction: multi-scan (CrysAlisPRO; Rigaku OD, 2015)	k = −21→21
Tmin = 0.899, Tmax = 1.000	l = −38→25
17424 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 0.5418P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.082	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.18 e Å^−3
11082 reflections	Δρmin = −0.21 e Å^−3
882 parameters	Absolute structure: Flack x determined using 4250 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
114 restraints	Absolute structure parameter: 0.03 (6)
Primary atom site location: iterative

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
B1	1.2958 (2)	0.72950 (14)	0.37278 (7)	0.0180 (4)
O1A	1.45819 (13)	0.76001 (9)	0.24034 (5)	0.0224 (3)
O2A	1.30654 (14)	0.68078 (9)	0.33406 (4)	0.0220 (3)
O3A	1.40431 (12)	0.78301 (9)	0.36886 (4)	0.0194 (3)
O4A	1.68429 (13)	0.68381 (9)	0.33268 (4)	0.0211 (3)
O5A	1.13290 (14)	0.73499 (9)	0.50856 (5)	0.0232 (3)
O6A	1.29684 (14)	0.68229 (9)	0.41160 (4)	0.0201 (3)
O7A	1.17500 (13)	0.77242 (9)	0.37473 (5)	0.0248 (3)
O8A	0.89394 (13)	0.70049 (9)	0.42678 (4)	0.0195 (3)
N1A	1.24905 (17)	0.74646 (12)	0.25902 (6)	0.0237 (4)
H1AA	1.196 (3)	0.7276 (17)	0.2780 (9)	0.029 (7)*
H1AB	1.216 (3)	0.7662 (16)	0.2348 (9)	0.027 (7)*
N4A	1.63574 (17)	0.73935 (11)	0.39666 (5)	0.0189 (3)
H4AA	1.580 (3)	0.7628 (17)	0.4108 (9)	0.028 (7)*
H4AB	1.706 (3)	0.7243 (16)	0.4097 (9)	0.026 (7)*
N5A	1.34181 (17)	0.74257 (12)	0.48811 (6)	0.0224 (4)
H5AA	1.397 (3)	0.7312 (15)	0.4660 (8)	0.021 (6)*
H5AB	1.368 (3)	0.7617 (16)	0.5120 (10)	0.027 (7)*
N8A	0.95049 (17)	0.70873 (12)	0.35647 (5)	0.0222 (4)
H8AA	0.875 (3)	0.6932 (16)	0.3479 (9)	0.027 (7)*
H8AB	1.003 (3)	0.723 (2)	0.3371 (11)	0.045 (9)*
C1A	1.37371 (19)	0.73872 (12)	0.26599 (6)	0.0181 (4)
C2A	1.41246 (18)	0.70139 (12)	0.30851 (6)	0.0172 (4)
H2A	1.4660	0.6552	0.3025	0.021*
C3A	1.49025 (18)	0.75811 (11)	0.33666 (6)	0.0160 (4)
H3A	1.5152	0.8028	0.3184	0.019*
C4A	1.61173 (17)	0.72273 (12)	0.35564 (6)	0.0162 (4)
C5A	1.21973 (18)	0.72566 (11)	0.48156 (6)	0.0165 (4)
C6A	1.18705 (18)	0.69372 (11)	0.43699 (6)	0.0159 (4)
H6A	1.1400	0.6443	0.4403	0.019*
C7A	1.10175 (18)	0.75131 (12)	0.41093 (6)	0.0167 (4)
H7A	1.0865	0.7976	0.4292	0.020*
C8A	0.97297 (18)	0.71726 (11)	0.39847 (6)	0.0158 (4)
B2	0.2156 (2)	0.25275 (13)	0.37085 (7)	0.0165 (4)
O1B	0.03861 (13)	0.21899 (9)	0.23953 (4)	0.0210 (3)
O2B	0.20792 (13)	0.29597 (9)	0.33032 (4)	0.0194 (3)
O3B	0.10527 (12)	0.20067 (8)	0.36941 (4)	0.0181 (3)
O4B	−0.18087 (13)	0.28519 (10)	0.32751 (4)	0.0222 (3)
O5B	0.37471 (13)	0.26014 (10)	0.50737 (5)	0.0240 (3)
O6B	0.21611 (13)	0.30520 (8)	0.40801 (4)	0.0175 (3)
O7B	0.33398 (13)	0.20833 (9)	0.37540 (5)	0.0213 (3)
O8B	0.61673 (13)	0.28362 (9)	0.42444 (4)	0.0186 (3)
N1B	0.25145 (16)	0.22739 (12)	0.25427 (6)	0.0221 (4)
H1BA	0.273 (3)	0.2087 (16)	0.2295 (10)	0.029 (7)*
H1BB	0.307 (3)	0.2480 (18)	0.2700 (10)	0.034 (8)*
N4B	−0.12216 (17)	0.25175 (11)	0.39542 (5)	0.0193 (3)
H4BA	−0.194 (3)	0.2671 (15)	0.4076 (9)	0.021 (6)*
H4BB	−0.063 (3)	0.2340 (16)	0.4111 (9)	0.026 (7)*
N5B	0.16555 (17)	0.25664 (12)	0.48745 (6)	0.0221 (4)
H5BA	0.140 (2)	0.2430 (15)	0.5129 (9)	0.019 (6)*
H5BB	0.112 (3)	0.2652 (17)	0.4672 (10)	0.034 (8)*
N8B	0.55632 (16)	0.27178 (12)	0.35469 (6)	0.0224 (4)
H8BA	0.499 (3)	0.2533 (17)	0.3373 (9)	0.027 (7)*
H8BB	0.632 (3)	0.2861 (19)	0.3449 (10)	0.041 (8)*
C1B	0.12887 (18)	0.23825 (11)	0.26348 (6)	0.0164 (4)
C2B	0.09760 (17)	0.27641 (11)	0.30647 (6)	0.0153 (4)
H2B	0.0453	0.3233	0.3011	0.018*
C3B	0.02093 (17)	0.22114 (11)	0.33602 (6)	0.0146 (3)
H3B	−0.0011	0.1744	0.3190	0.018*
C4B	−0.10308 (17)	0.25638 (11)	0.35312 (6)	0.0156 (4)
C5B	0.28899 (18)	0.26830 (12)	0.48007 (6)	0.0171 (4)
C6B	0.32432 (18)	0.29402 (12)	0.43448 (6)	0.0156 (4)
H6B	0.3740	0.3428	0.4363	0.019*
C7B	0.40749 (17)	0.23289 (12)	0.41078 (6)	0.0155 (4)
H7B	0.4224	0.1888	0.4307	0.019*
C8B	0.53654 (17)	0.26521 (11)	0.39672 (6)	0.0155 (4)
O1W	0.3256 (2)	0.42869 (12)	0.29928 (8)	0.0374 (5)	0.88
H1WA	0.2970	0.3883	0.3125	0.056*	0.88
H1WB	0.2806	0.4661	0.3099	0.056*	0.88
O1X	0.3560 (16)	0.4321 (10)	0.3258 (6)	0.038 (4)	0.12
H1XA	0.3405	0.3899	0.3396	0.057*	0.12
H1XB	0.2930	0.4361	0.3074	0.057*	0.12
O2W	0.58211 (19)	0.41798 (12)	0.28031 (8)	0.0480 (5)
H2WA	0.5045	0.4312	0.2876	0.072*
H2WB	0.5753	0.3704	0.2727	0.072*
O3W	0.7654 (2)	0.49277 (13)	0.23023 (8)	0.0347 (4)	0.9
H3WA	0.711 (4)	0.469 (2)	0.2452 (14)	0.052*	0.9
H3WB	0.808 (4)	0.512 (3)	0.2476 (16)	0.052*	0.9
O4W	0.97336 (18)	0.56156 (11)	0.27495 (6)	0.0380 (4)
H4WA	0.9640	0.6112	0.2727	0.057*
H4WB	1.0225	0.5468	0.2962	0.057*
O5W	1.17416 (15)	0.54333 (9)	0.33390 (6)	0.0286 (3)
H5WA	1.1641	0.5160	0.3571	0.21 (3)*
H5WB	1.2135	0.5882	0.3325	0.057 (10)*
O6W	1.14776 (19)	0.46307 (10)	0.41027 (6)	0.0387 (4)
H6WA	1.1726	0.4170	0.4039	0.058*
H6WB	1.1922	0.4750	0.4331	0.058*
O7W	1.2537 (3)	0.5051 (2)	0.48675 (12)	0.0442 (8)	0.75
H7WA	1.2083	0.5353	0.5031	0.066*	0.75
H7WB	1.2966	0.4753	0.5050	0.066*	0.75
O7X	1.2057 (10)	0.5074 (7)	0.4984 (3)	0.039 (3)	0.25
H7XA	1.2317	0.4693	0.4826	0.059*	0.25
H7XB	1.1400	0.4895	0.5125	0.059*	0.25
O8W	1.0639 (4)	0.5856 (2)	0.52960 (12)	0.0448 (10)	0.72
H8WA	1.0638	0.6350	0.5268	0.067*	0.72
H8WB	1.0234	0.5845	0.5547	0.067*	0.72
O8X	1.0305 (9)	0.5904 (6)	0.5446 (3)	0.0342 (18)	0.28
H8XA	0.9992	0.6242	0.5269	0.051*	0.28
H8XB	1.0953	0.5707	0.5307	0.051*	0.28
O9W	0.9257 (3)	0.56438 (15)	0.60373 (9)	0.0438 (6)	0.75
H9WA	0.8891	0.5304	0.6129	0.066*	0.75
H9WB	0.9042	0.6095	0.6156	0.066*	0.75
O9X	0.8105 (9)	0.5580 (6)	0.5964 (3)	0.055 (2)	0.25
H9XA	0.7925	0.5745	0.6223	0.083*	0.25
H9XB	0.8773	0.5282	0.5976	0.083*	0.25
O10W	0.8559 (2)	0.44021 (11)	0.65939 (7)	0.0480 (5)
H10A	0.8411	0.3942	0.6501	0.072*
H10B	0.8047	0.4545	0.6830	0.072*
O11W	0.6539 (2)	0.57635 (13)	0.65094 (8)	0.0332 (5)	0.75
H11C	0.6889	0.5678	0.6760	0.050*	0.75
H11D	0.6661	0.6248	0.6464	0.050*	0.75
O12W	0.5854 (4)	0.4475 (3)	0.59897 (13)	0.0378 (9)	0.77
H12D	0.6127	0.4065	0.6118	0.057*	0.77
H12E	0.6285	0.4783	0.6134	0.057*	0.77
O12X	0.6193 (17)	0.4415 (11)	0.5842 (5)	0.046 (4)	0.23
H12F	0.6535	0.4860	0.5794	0.069*	0.23
H12G	0.6813	0.4093	0.5794	0.069*	0.23
O13W	0.43260 (19)	0.41560 (12)	0.52737 (6)	0.0421 (5)
H13C	0.4830	0.4286	0.5486	0.101 (17)*
H13D	0.4287	0.3716	0.5224	0.043 (10)*
N10	0.2598 (2)	0.51035 (11)	0.66146 (6)	0.0310 (5)
C11	0.2453 (2)	0.57970 (13)	0.63246 (7)	0.0298 (5)
H11A	0.2421	0.6258	0.6509	0.036*
H11B	0.1619	0.5760	0.6172	0.036*
C12	0.3509 (3)	0.59019 (14)	0.59907 (8)	0.0331 (5)
H12A	0.3512	0.5466	0.5793	0.050*
H12B	0.4342	0.5936	0.6137	0.050*
H12C	0.3353	0.6372	0.5827	0.050*
C13	0.3832 (3)	0.51455 (15)	0.68755 (9)	0.0401 (6)
H13A	0.4569	0.5108	0.6674	0.048*
H13B	0.3869	0.4697	0.7070	0.048*
C14	0.3997 (3)	0.58621 (17)	0.71475 (10)	0.0503 (8)
H14A	0.4017	0.6310	0.6958	0.076*
H14B	0.4804	0.5831	0.7310	0.076*
H14C	0.3275	0.5907	0.7350	0.076*
C15	0.1417 (3)	0.50970 (15)	0.69068 (8)	0.0378 (6)
H15A	0.1424	0.5568	0.7083	0.045*
H15B	0.0641	0.5113	0.6722	0.045*
C16	0.1303 (4)	0.44167 (15)	0.72102 (9)	0.0461 (7)
H16A	0.1206	0.3948	0.7040	0.069*
H16B	0.0551	0.4483	0.7397	0.069*
H16C	0.2079	0.4381	0.7389	0.069*
C17	0.2687 (3)	0.43787 (13)	0.63473 (7)	0.0304 (5)
H17A	0.3485	0.4399	0.6173	0.036*
H17B	0.2763	0.3939	0.6547	0.036*
C18	0.1570 (2)	0.42356 (14)	0.60465 (8)	0.0310 (5)
H18A	0.1499	0.4658	0.5840	0.047*
H18B	0.0775	0.4198	0.6215	0.047*
H18C	0.1711	0.3758	0.5889	0.047*
N20	0.6954 (5)	0.5036 (4)	0.43678 (18)	0.0240 (10)	0.55
C28B	0.8698 (6)	0.4530 (4)	0.4876 (2)	0.0402 (15)	0.55
H28A	0.9343	0.4675	0.4661	0.060*	0.55
H28B	0.8976	0.4064	0.5025	0.060*	0.55
H28C	0.8599	0.4942	0.5087	0.060*	0.55
C21	0.7890 (11)	0.5219 (8)	0.4008 (3)	0.0260 (16)	0.55
H21A	0.7517	0.5642	0.3837	0.031*	0.55
H21B	0.8685	0.5417	0.4144	0.031*	0.55
C22	0.806 (2)	0.4550 (14)	0.3714 (7)	0.039 (4)	0.45
H22D	0.8422	0.4084	0.3839	0.058*	0.45
H22E	0.8557	0.4699	0.3459	0.058*	0.45
H22F	0.7163	0.4456	0.3629	0.058*	0.45
C23A	0.6782 (5)	0.5764 (3)	0.46224 (17)	0.0308 (10)	0.55
H23A	0.6479	0.6167	0.4423	0.037*	0.55
H23B	0.7632	0.5923	0.4734	0.037*	0.55
C23B	0.7325 (6)	0.5689 (3)	0.4748 (2)	0.0294 (11)	0.45
H23C	0.6990	0.6138	0.4589	0.035*	0.45
H23D	0.8240	0.5789	0.4815	0.035*	0.45
C24A	0.5850 (6)	0.5716 (3)	0.50000 (19)	0.0433 (13)	0.55
H24A	0.5042	0.5486	0.4903	0.065*	0.55
H24B	0.5682	0.6230	0.5111	0.065*	0.55
H24C	0.6226	0.5402	0.5230	0.065*	0.55
C24B	0.6592 (8)	0.5617 (4)	0.5171 (2)	0.0459 (17)	0.45
H24D	0.5678	0.5537	0.5111	0.069*	0.45
H24E	0.6700	0.6085	0.5341	0.069*	0.45
H24F	0.6928	0.5182	0.5336	0.069*	0.45
C25A	0.5693 (6)	0.4763 (4)	0.4171 (2)	0.0301 (12)	0.55
H25A	0.5863	0.4287	0.4008	0.036*	0.55
H25B	0.5096	0.4636	0.4409	0.036*	0.55
C25B	0.5859 (8)	0.4834 (5)	0.4319 (3)	0.0310 (14)	0.45
H25C	0.5859	0.4368	0.4139	0.037*	0.45
H25D	0.5361	0.4718	0.4584	0.037*	0.45
C26A	0.5158 (8)	0.5457 (5)	0.4073 (3)	0.053 (2)	0.45
H26D	0.5226	0.5939	0.4232	0.080*	0.45
H26E	0.4250	0.5318	0.4042	0.080*	0.45
H26F	0.5545	0.5516	0.3786	0.080*	0.45
C26B	0.5020 (7)	0.5321 (4)	0.3869 (2)	0.0403 (13)	0.55
H26A	0.4744	0.5770	0.4033	0.060*	0.55
H26B	0.4269	0.5073	0.3739	0.060*	0.55
H26C	0.5615	0.5478	0.3640	0.060*	0.55
C27A	0.7754 (8)	0.4297 (5)	0.4668 (3)	0.0255 (15)	0.45
H27C	0.7717	0.3873	0.4457	0.031*	0.45
H27D	0.7168	0.4166	0.4910	0.031*	0.45
C28A	0.9105 (8)	0.4340 (5)	0.4845 (3)	0.0403 (19)	0.45
H28D	0.9697	0.4486	0.4613	0.060*	0.45
H28E	0.9354	0.3841	0.4960	0.060*	0.45
H28F	0.9141	0.4722	0.5076	0.060*	0.45
C27B	0.7429 (7)	0.4387 (4)	0.4654 (3)	0.0271 (13)	0.55
H27A	0.6771	0.4285	0.4878	0.033*	0.55
H27B	0.7509	0.3921	0.4475	0.033*	0.55
N20A	0.7251 (7)	0.5003 (5)	0.4453 (2)	0.0249 (12)	0.45
C21A	0.8102 (13)	0.5214 (9)	0.4061 (4)	0.0250 (19)	0.45
H21C	0.9000	0.5295	0.4158	0.030*	0.45
H21D	0.7790	0.5695	0.3930	0.030*	0.45
C22A	0.8269 (17)	0.4610 (10)	0.3702 (5)	0.029 (2)	0.55
H22A	0.8636	0.4180	0.3862	0.044*	0.55
H22B	0.8910	0.4810	0.3499	0.044*	0.55
H22C	0.7511	0.4437	0.3541	0.044*	0.55
O3X	0.749 (2)	0.5156 (15)	0.2519 (9)	0.041 (5)	0.1
H3XA	0.7111	0.5280	0.2760	0.062*	0.1
H3XB	0.7332	0.5536	0.2346	0.062*	0.1

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0158 (10)	0.0232 (11)	0.0151 (9)	−0.0013 (8)	−0.0039 (8)	0.0013 (9)
O1A	0.0168 (6)	0.0360 (8)	0.0144 (6)	−0.0029 (6)	0.0020 (5)	0.0038 (6)
O2A	0.0240 (7)	0.0297 (8)	0.0124 (6)	−0.0129 (6)	−0.0001 (5)	−0.0002 (6)
O3A	0.0144 (6)	0.0227 (7)	0.0211 (7)	−0.0016 (5)	0.0000 (5)	−0.0060 (6)
O4A	0.0173 (6)	0.0313 (8)	0.0147 (6)	0.0019 (6)	0.0003 (5)	−0.0025 (6)
O5A	0.0190 (6)	0.0339 (8)	0.0167 (7)	0.0019 (6)	0.0035 (5)	−0.0024 (6)
O6A	0.0211 (7)	0.0270 (8)	0.0122 (6)	0.0079 (6)	0.0007 (5)	0.0015 (5)
O7A	0.0150 (6)	0.0332 (8)	0.0263 (7)	0.0023 (6)	0.0005 (6)	0.0158 (7)
O8A	0.0166 (6)	0.0294 (8)	0.0126 (6)	−0.0004 (6)	0.0016 (5)	0.0016 (6)
N1A	0.0144 (8)	0.0413 (11)	0.0155 (8)	−0.0017 (8)	−0.0016 (6)	0.0034 (8)
N4A	0.0157 (8)	0.0282 (9)	0.0128 (8)	−0.0005 (7)	−0.0018 (6)	−0.0011 (7)
N5A	0.0172 (8)	0.0351 (10)	0.0148 (8)	0.0000 (7)	−0.0018 (7)	−0.0041 (7)
N8A	0.0172 (8)	0.0390 (11)	0.0105 (7)	0.0007 (8)	0.0002 (6)	−0.0014 (7)
C1A	0.0184 (9)	0.0233 (10)	0.0124 (8)	−0.0010 (8)	−0.0018 (7)	−0.0016 (7)
C2A	0.0164 (8)	0.0225 (10)	0.0126 (8)	−0.0040 (7)	−0.0022 (7)	0.0008 (7)
C3A	0.0150 (8)	0.0188 (9)	0.0140 (8)	−0.0036 (7)	−0.0013 (7)	−0.0004 (7)
C4A	0.0143 (8)	0.0205 (9)	0.0137 (8)	−0.0040 (7)	0.0003 (7)	0.0021 (7)
C5A	0.0180 (9)	0.0179 (9)	0.0136 (8)	0.0016 (7)	−0.0008 (7)	0.0008 (7)
C6A	0.0164 (8)	0.0176 (9)	0.0136 (8)	0.0017 (7)	−0.0003 (7)	0.0009 (7)
C7A	0.0150 (8)	0.0186 (9)	0.0166 (9)	0.0011 (7)	−0.0010 (7)	0.0029 (7)
C8A	0.0158 (8)	0.0180 (9)	0.0135 (8)	0.0031 (7)	−0.0010 (7)	−0.0009 (7)
B2	0.0131 (9)	0.0234 (11)	0.0129 (9)	−0.0008 (8)	0.0029 (7)	−0.0015 (8)
O1B	0.0163 (6)	0.0322 (8)	0.0145 (6)	−0.0020 (6)	−0.0023 (5)	−0.0030 (6)
O2B	0.0199 (6)	0.0269 (8)	0.0114 (6)	−0.0107 (6)	−0.0001 (5)	0.0005 (5)
O3B	0.0130 (6)	0.0228 (7)	0.0185 (6)	−0.0007 (5)	−0.0005 (5)	0.0070 (5)
O4B	0.0155 (6)	0.0379 (9)	0.0133 (6)	0.0023 (6)	−0.0005 (5)	0.0014 (6)
O5B	0.0177 (6)	0.0402 (9)	0.0142 (7)	0.0044 (6)	−0.0026 (5)	0.0017 (6)
O6B	0.0167 (6)	0.0241 (7)	0.0118 (6)	0.0066 (5)	−0.0016 (5)	−0.0010 (5)
O7B	0.0132 (6)	0.0293 (8)	0.0214 (7)	0.0025 (6)	−0.0006 (5)	−0.0109 (6)
O8B	0.0141 (6)	0.0288 (8)	0.0131 (6)	0.0005 (6)	−0.0005 (5)	−0.0012 (6)
N1B	0.0137 (8)	0.0369 (10)	0.0155 (8)	−0.0016 (7)	0.0010 (6)	−0.0055 (7)
N4B	0.0155 (8)	0.0298 (9)	0.0127 (7)	0.0014 (7)	0.0011 (6)	0.0002 (7)
N5B	0.0153 (8)	0.0390 (11)	0.0121 (8)	−0.0002 (7)	0.0012 (6)	0.0029 (7)
N8B	0.0143 (8)	0.0415 (11)	0.0114 (8)	−0.0013 (7)	−0.0005 (6)	0.0026 (7)
C1B	0.0163 (8)	0.0208 (9)	0.0119 (8)	−0.0017 (7)	0.0016 (7)	0.0013 (7)
C2B	0.0150 (8)	0.0191 (9)	0.0117 (8)	−0.0025 (7)	0.0018 (7)	0.0017 (7)
C3B	0.0139 (8)	0.0163 (9)	0.0136 (8)	−0.0014 (7)	0.0010 (7)	0.0010 (7)
C4B	0.0140 (8)	0.0204 (9)	0.0123 (8)	−0.0023 (7)	0.0007 (7)	−0.0010 (7)
C5B	0.0171 (9)	0.0218 (10)	0.0123 (8)	0.0011 (7)	0.0007 (7)	−0.0018 (7)
C6B	0.0143 (8)	0.0214 (9)	0.0113 (8)	0.0011 (7)	0.0010 (7)	−0.0012 (7)
C7B	0.0130 (8)	0.0205 (9)	0.0129 (8)	0.0018 (7)	0.0014 (6)	−0.0008 (7)
C8B	0.0134 (8)	0.0199 (9)	0.0130 (8)	0.0036 (7)	0.0018 (6)	0.0011 (7)
O1W	0.0365 (11)	0.0237 (10)	0.0520 (14)	−0.0014 (8)	0.0178 (11)	0.0051 (10)
O1X	0.040 (8)	0.039 (9)	0.035 (8)	−0.005 (7)	0.011 (7)	−0.003 (7)
O2W	0.0402 (10)	0.0301 (10)	0.0738 (15)	−0.0034 (8)	0.0181 (10)	0.0013 (10)
O3W	0.0338 (11)	0.0335 (11)	0.0367 (12)	−0.0053 (9)	0.0025 (9)	0.0038 (10)
O4W	0.0431 (10)	0.0318 (9)	0.0390 (10)	0.0056 (8)	−0.0121 (8)	0.0018 (8)
O5W	0.0285 (8)	0.0221 (8)	0.0352 (9)	−0.0033 (6)	−0.0047 (7)	0.0038 (7)
O6W	0.0490 (11)	0.0275 (9)	0.0396 (10)	0.0049 (8)	−0.0067 (8)	0.0004 (7)
O7W	0.046 (2)	0.0518 (19)	0.035 (2)	0.0083 (18)	−0.0015 (14)	−0.0017 (15)
O7X	0.042 (6)	0.055 (5)	0.021 (5)	0.024 (5)	−0.007 (4)	−0.013 (4)
O8W	0.061 (2)	0.0326 (16)	0.041 (2)	−0.0013 (15)	0.0235 (16)	0.0033 (16)
O8X	0.045 (5)	0.028 (4)	0.030 (5)	−0.003 (4)	0.002 (4)	0.002 (4)
O9W	0.0622 (17)	0.0260 (12)	0.0433 (15)	0.0015 (11)	0.0223 (13)	−0.0032 (11)
O9X	0.058 (5)	0.071 (6)	0.037 (4)	−0.035 (5)	0.006 (4)	−0.004 (4)
O10W	0.0627 (13)	0.0304 (10)	0.0509 (12)	−0.0086 (9)	0.0011 (10)	−0.0076 (9)
O11W	0.0386 (12)	0.0247 (11)	0.0362 (12)	−0.0002 (9)	−0.0069 (10)	0.0081 (9)
O12W	0.049 (2)	0.0228 (13)	0.042 (2)	−0.0009 (16)	−0.0211 (17)	0.0038 (17)
O12X	0.047 (8)	0.042 (8)	0.049 (9)	−0.011 (6)	−0.004 (6)	0.020 (7)
O13W	0.0456 (11)	0.0393 (11)	0.0414 (10)	−0.0062 (9)	−0.0141 (9)	0.0034 (9)
N10	0.0543 (13)	0.0163 (9)	0.0225 (9)	−0.0013 (9)	−0.0118 (9)	0.0001 (7)
C11	0.0468 (13)	0.0165 (10)	0.0261 (11)	0.0007 (10)	−0.0077 (10)	0.0030 (9)
C12	0.0446 (14)	0.0216 (11)	0.0332 (12)	−0.0026 (10)	−0.0065 (11)	0.0032 (9)
C13	0.0631 (17)	0.0233 (12)	0.0339 (13)	0.0011 (12)	−0.0233 (12)	−0.0014 (10)
C14	0.073 (2)	0.0367 (16)	0.0416 (15)	−0.0026 (14)	−0.0236 (15)	−0.0109 (13)
C15	0.0660 (18)	0.0231 (12)	0.0243 (11)	−0.0021 (12)	−0.0011 (11)	0.0003 (9)
C16	0.080 (2)	0.0293 (13)	0.0285 (13)	−0.0067 (14)	−0.0026 (13)	0.0042 (11)
C17	0.0487 (14)	0.0168 (10)	0.0257 (11)	0.0005 (10)	−0.0094 (10)	−0.0015 (8)
C18	0.0439 (13)	0.0220 (11)	0.0272 (11)	−0.0029 (10)	−0.0059 (10)	−0.0028 (9)
N20	0.027 (2)	0.0164 (17)	0.0289 (18)	−0.0048 (14)	0.0024 (14)	0.0011 (14)
C28B	0.035 (3)	0.043 (4)	0.042 (3)	−0.010 (2)	−0.009 (3)	0.009 (3)
C21	0.024 (3)	0.028 (2)	0.027 (2)	−0.008 (2)	−0.001 (2)	0.0005 (18)
C22	0.051 (9)	0.032 (4)	0.033 (4)	−0.013 (4)	0.018 (4)	−0.005 (3)
C23A	0.038 (2)	0.0210 (18)	0.033 (2)	−0.0056 (16)	0.0057 (18)	−0.0021 (15)
C23B	0.035 (3)	0.019 (2)	0.034 (2)	−0.0015 (19)	0.012 (2)	−0.0009 (17)
C24A	0.057 (3)	0.026 (2)	0.047 (3)	−0.010 (2)	0.021 (2)	−0.007 (2)
C24B	0.070 (4)	0.023 (3)	0.045 (3)	−0.007 (3)	0.031 (3)	−0.005 (2)
C25A	0.027 (2)	0.025 (2)	0.039 (3)	−0.0051 (14)	−0.0002 (18)	−0.0028 (19)
C25B	0.027 (2)	0.021 (3)	0.045 (4)	0.0026 (17)	0.003 (2)	0.004 (2)
C26A	0.035 (3)	0.038 (4)	0.088 (6)	0.002 (3)	−0.011 (4)	0.024 (4)
C26B	0.038 (3)	0.035 (3)	0.048 (3)	0.004 (2)	−0.006 (2)	0.000 (2)
C27A	0.028 (3)	0.020 (2)	0.028 (3)	0.0025 (19)	0.006 (2)	0.0022 (18)
C28A	0.033 (3)	0.032 (4)	0.056 (4)	0.004 (2)	−0.007 (3)	0.000 (3)
C27B	0.029 (3)	0.021 (2)	0.032 (2)	−0.0048 (17)	−0.001 (2)	0.0004 (17)
N20A	0.025 (2)	0.019 (2)	0.031 (2)	0.0010 (17)	0.0072 (17)	0.0020 (16)
C21A	0.025 (4)	0.022 (3)	0.028 (3)	0.000 (3)	0.005 (3)	0.002 (2)
C22A	0.032 (4)	0.029 (4)	0.027 (3)	−0.010 (3)	0.002 (3)	0.000 (3)
O3X	0.043 (7)	0.045 (7)	0.035 (7)	−0.009 (6)	−0.004 (6)	−0.001 (6)

Geometric parameters (Å, º)

B1—O2A	1.475 (3)	O10W—H10B	0.9389
B1—O3A	1.473 (3)	O11W—H11C	0.8697
B1—O6A	1.458 (3)	O11W—H11D	0.8702
B1—O7A	1.466 (3)	O12W—H12D	0.8699
O1A—C1A	1.241 (3)	O12W—H12E	0.8311
O2A—C2A	1.403 (2)	O12X—H12F	0.8701
O3A—C3A	1.408 (2)	O12X—H12G	0.8698
O4A—C4A	1.241 (2)	O13W—H13C	0.8697
O5A—C5A	1.241 (2)	O13W—H13D	0.7875
O6A—C6A	1.400 (2)	N10—C11	1.518 (3)
O7A—C7A	1.404 (2)	N10—C13	1.518 (3)
O8A—C8A	1.236 (2)	N10—C15	1.525 (4)
N1A—H1AA	0.87 (3)	N10—C17	1.518 (3)
N1A—H1AB	0.89 (3)	C11—H11A	0.9900
N1A—C1A	1.322 (3)	C11—H11B	0.9900
N4A—H4AA	0.84 (3)	C11—C12	1.519 (4)
N4A—H4AB	0.88 (3)	C12—H12A	0.9800
N4A—C4A	1.325 (2)	C12—H12B	0.9800
N5A—H5AA	0.92 (3)	C12—H12C	0.9800
N5A—H5AB	0.85 (3)	C13—H13A	0.9900
N5A—C5A	1.320 (3)	C13—H13B	0.9900
N8A—H8AA	0.87 (3)	C13—C14	1.521 (4)
N8A—H8AB	0.85 (4)	C14—H14A	0.9800
N8A—C8A	1.328 (2)	C14—H14B	0.9800
C1A—C2A	1.523 (3)	C14—H14C	0.9800
C2A—H2A	1.0000	C15—H15A	0.9900
C2A—C3A	1.550 (3)	C15—H15B	0.9900
C3A—H3A	1.0000	C15—C16	1.522 (3)
C3A—C4A	1.525 (3)	C16—H16A	0.9800
C5A—C6A	1.526 (2)	C16—H16B	0.9800
C6A—H6A	1.0000	C16—H16C	0.9800
C6A—C7A	1.567 (3)	C17—H17A	0.9900
C7A—H7A	1.0000	C17—H17B	0.9900
C7A—C8A	1.516 (3)	C17—C18	1.510 (3)
B2—O2B	1.467 (2)	C18—H18A	0.9800
B2—O3B	1.467 (3)	C18—H18B	0.9800
B2—O6B	1.472 (2)	C18—H18C	0.9800
B2—O7B	1.464 (2)	N20—C21	1.513 (10)
O1B—C1B	1.243 (2)	N20—C23A	1.510 (7)
O2B—C2B	1.407 (2)	N20—C25A	1.523 (6)
O3B—C3B	1.402 (2)	N20—C27B	1.524 (7)
O4B—C4B	1.240 (2)	C28B—H28A	0.9800
O5B—C5B	1.236 (2)	C28B—H28B	0.9800
O6B—C6B	1.405 (2)	C28B—H28C	0.9800
O7B—C7B	1.403 (2)	C28B—C27B	1.509 (7)
O8B—C8B	1.239 (2)	C21—H21A	0.9900
N1B—H1BA	0.86 (3)	C21—H21B	0.9900
N1B—H1BB	0.84 (3)	C21—C22A	1.48 (2)
N1B—C1B	1.320 (3)	C22—H22D	0.9800
N4B—H4BA	0.88 (3)	C22—H22E	0.9800
N4B—H4BB	0.85 (3)	C22—H22F	0.9800
N4B—C4B	1.326 (2)	C22—C21A	1.58 (3)
N5B—H5BA	0.86 (3)	C23A—H23A	0.9900
N5B—H5BB	0.85 (3)	C23A—H23B	0.9900
N5B—C5B	1.320 (3)	C23A—C24A	1.520 (7)
N8B—H8BA	0.87 (3)	C23B—H23C	0.9900
N8B—H8BB	0.88 (3)	C23B—H23D	0.9900
N8B—C8B	1.321 (2)	C23B—C24B	1.520 (8)
C1B—C2B	1.523 (2)	C23B—N20A	1.511 (9)
C2B—H2B	1.0000	C24A—H24A	0.9800
C2B—C3B	1.552 (2)	C24A—H24B	0.9800
C3B—H3B	1.0000	C24A—H24C	0.9800
C3B—C4B	1.525 (2)	C24B—H24D	0.9800
C5B—C6B	1.525 (2)	C24B—H24E	0.9800
C6B—H6B	1.0000	C24B—H24F	0.9800
C6B—C7B	1.560 (3)	C25A—H25A	0.9900
C7B—H7B	1.0000	C25A—H25B	0.9900
C7B—C8B	1.521 (3)	C25A—C26B	1.522 (8)
O1W—H1WA	0.8699	C25B—H25C	0.9900
O1W—H1WB	0.8700	C25B—H25D	0.9900
O1X—H1XA	0.8693	C25B—C26A	1.518 (9)
O1X—H1XB	0.8702	C25B—N20A	1.535 (8)
O2W—H2WA	0.8702	C26A—H26D	0.9800
O2W—H2WB	0.8696	C26A—H26E	0.9800
O3W—H3WA	0.84 (4)	C26A—H26F	0.9800
O3W—H3WB	0.78 (5)	C26B—H26A	0.9800
O4W—H4WA	0.8784	C26B—H26B	0.9800
O4W—H4WB	0.8720	C26B—H26C	0.9800
O5W—H5WA	0.8699	C27A—H27C	0.9900
O5W—H5WB	0.8871	C27A—H27D	0.9900
O6W—H6WA	0.8701	C27A—C28A	1.510 (10)
O6W—H6WB	0.8702	C27A—N20A	1.500 (9)
O7W—H7WA	0.8706	C28A—H28D	0.9800
O7W—H7WB	0.8891	C28A—H28E	0.9800
O7X—H7XA	0.8696	C28A—H28F	0.9800
O7X—H7XB	0.8704	C27B—H27A	0.9900
O8W—H8WA	0.8701	C27B—H27B	0.9900
O8W—H8WB	0.8825	N20A—C21A	1.545 (13)
O8X—H8XA	0.8701	C21A—H21C	0.9900
O8X—H8XB	0.8704	C21A—H21D	0.9900
O9W—H9WA	0.7630	C22A—H22A	0.9800
O9W—H9WB	0.8998	C22A—H22B	0.9800
O9X—H9XA	0.8703	C22A—H22C	0.9800
O9X—H9XB	0.8701	O3X—H3XA	0.8705
O10W—H10A	0.8697	O3X—H3XB	0.8700
O3A—B1—O2A	104.11 (16)	H12A—C12—H12B	109.5
O6A—B1—O2A	109.84 (17)	H12A—C12—H12C	109.5
O6A—B1—O3A	115.05 (16)	H12B—C12—H12C	109.5
O6A—B1—O7A	105.29 (16)	N10—C13—H13A	108.4
O7A—B1—O2A	113.30 (16)	N10—C13—H13B	108.4
O7A—B1—O3A	109.49 (17)	N10—C13—C14	115.4 (2)
C2A—O2A—B1	111.57 (15)	H13A—C13—H13B	107.5
C3A—O3A—B1	110.35 (15)	C14—C13—H13A	108.4
C6A—O6A—B1	111.99 (15)	C14—C13—H13B	108.4
C7A—O7A—B1	111.28 (15)	C13—C14—H14A	109.5
H1AA—N1A—H1AB	118 (3)	C13—C14—H14B	109.5
C1A—N1A—H1AA	118.3 (19)	C13—C14—H14C	109.5
C1A—N1A—H1AB	123.9 (18)	H14A—C14—H14B	109.5
H4AA—N4A—H4AB	120 (3)	H14A—C14—H14C	109.5
C4A—N4A—H4AA	118 (2)	H14B—C14—H14C	109.5
C4A—N4A—H4AB	122.1 (18)	N10—C15—H15A	108.4
H5AA—N5A—H5AB	122 (3)	N10—C15—H15B	108.4
C5A—N5A—H5AA	116.3 (16)	H15A—C15—H15B	107.4
C5A—N5A—H5AB	121.6 (19)	C16—C15—N10	115.7 (2)
H8AA—N8A—H8AB	117 (3)	C16—C15—H15A	108.4
C8A—N8A—H8AA	119.3 (18)	C16—C15—H15B	108.4
C8A—N8A—H8AB	123 (2)	C15—C16—H16A	109.5
O1A—C1A—N1A	124.03 (19)	C15—C16—H16B	109.5
O1A—C1A—C2A	119.57 (17)	C15—C16—H16C	109.5
N1A—C1A—C2A	116.40 (18)	H16A—C16—H16B	109.5
O2A—C2A—C1A	112.89 (16)	H16A—C16—H16C	109.5
O2A—C2A—H2A	109.5	H16B—C16—H16C	109.5
O2A—C2A—C3A	105.00 (15)	N10—C17—H17A	108.4
C1A—C2A—H2A	109.5	N10—C17—H17B	108.4
C1A—C2A—C3A	110.34 (16)	H17A—C17—H17B	107.5
C3A—C2A—H2A	109.5	C18—C17—N10	115.3 (2)
O3A—C3A—C2A	105.35 (15)	C18—C17—H17A	108.4
O3A—C3A—H3A	108.7	C18—C17—H17B	108.4
O3A—C3A—C4A	112.35 (15)	C17—C18—H18A	109.5
C2A—C3A—H3A	108.7	C17—C18—H18B	109.5
C4A—C3A—C2A	112.83 (16)	C17—C18—H18C	109.5
C4A—C3A—H3A	108.7	H18A—C18—H18B	109.5
O4A—C4A—N4A	123.64 (18)	H18A—C18—H18C	109.5
O4A—C4A—C3A	120.49 (17)	H18B—C18—H18C	109.5
N4A—C4A—C3A	115.79 (17)	C21—N20—C25A	109.0 (5)
O5A—C5A—N5A	124.59 (18)	C21—N20—C27B	112.2 (6)
O5A—C5A—C6A	119.60 (17)	C23A—N20—C21	106.3 (6)
N5A—C5A—C6A	115.81 (17)	C23A—N20—C25A	111.8 (5)
O6A—C6A—C5A	112.17 (15)	C23A—N20—C27B	111.5 (5)
O6A—C6A—H6A	109.5	C25A—N20—C27B	106.2 (5)
O6A—C6A—C7A	105.40 (14)	H28A—C28B—H28B	109.5
C5A—C6A—H6A	109.5	H28A—C28B—H28C	109.5
C5A—C6A—C7A	110.75 (16)	H28B—C28B—H28C	109.5
C7A—C6A—H6A	109.5	C27B—C28B—H28A	109.5
O7A—C7A—C6A	105.81 (15)	C27B—C28B—H28B	109.5
O7A—C7A—H7A	108.8	C27B—C28B—H28C	109.5
O7A—C7A—C8A	112.36 (16)	N20—C21—H21A	107.5
C6A—C7A—H7A	108.8	N20—C21—H21B	107.5
C8A—C7A—C6A	112.18 (16)	H21A—C21—H21B	107.0
C8A—C7A—H7A	108.8	C22A—C21—N20	119.3 (12)
O8A—C8A—N8A	123.27 (18)	C22A—C21—H21A	107.5
O8A—C8A—C7A	120.06 (16)	C22A—C21—H21B	107.5
N8A—C8A—C7A	116.65 (17)	H22D—C22—H22E	109.5
O2B—B2—O3B	104.64 (15)	H22D—C22—H22F	109.5
O2B—B2—O6B	110.18 (17)	H22E—C22—H22F	109.5
O3B—B2—O6B	114.53 (15)	C21A—C22—H22D	109.5
O7B—B2—O2B	113.74 (16)	C21A—C22—H22E	109.5
O7B—B2—O3B	109.28 (17)	C21A—C22—H22F	109.5
O7B—B2—O6B	104.73 (15)	N20—C23A—H23A	108.4
C2B—O2B—B2	111.51 (14)	N20—C23A—H23B	108.4
C3B—O3B—B2	110.65 (14)	N20—C23A—C24A	115.5 (4)
C6B—O6B—B2	111.75 (14)	H23A—C23A—H23B	107.5
C7B—O7B—B2	111.74 (15)	C24A—C23A—H23A	108.4
H1BA—N1B—H1BB	120 (3)	C24A—C23A—H23B	108.4
C1B—N1B—H1BA	119.9 (18)	H23C—C23B—H23D	107.5
C1B—N1B—H1BB	119 (2)	C24B—C23B—H23C	108.4
H4BA—N4B—H4BB	119 (2)	C24B—C23B—H23D	108.4
C4B—N4B—H4BA	122.1 (17)	N20A—C23B—H23C	108.4
C4B—N4B—H4BB	118.5 (19)	N20A—C23B—H23D	108.4
H5BA—N5B—H5BB	121 (3)	N20A—C23B—C24B	115.4 (5)
C5B—N5B—H5BA	120.1 (17)	C23A—C24A—H24A	109.5
C5B—N5B—H5BB	119 (2)	C23A—C24A—H24B	109.5
H8BA—N8B—H8BB	121 (3)	C23A—C24A—H24C	109.5
C8B—N8B—H8BA	118.0 (19)	H24A—C24A—H24B	109.5
C8B—N8B—H8BB	120 (2)	H24A—C24A—H24C	109.5
O1B—C1B—N1B	124.20 (18)	H24B—C24A—H24C	109.5
O1B—C1B—C2B	118.56 (17)	C23B—C24B—H24D	109.5
N1B—C1B—C2B	117.24 (17)	C23B—C24B—H24E	109.5
O2B—C2B—C1B	112.97 (15)	C23B—C24B—H24F	109.5
O2B—C2B—H2B	109.4	H24D—C24B—H24E	109.5
O2B—C2B—C3B	105.23 (14)	H24D—C24B—H24F	109.5
C1B—C2B—H2B	109.4	H24E—C24B—H24F	109.5
C1B—C2B—C3B	110.45 (16)	N20—C25A—H25A	108.3
C3B—C2B—H2B	109.4	N20—C25A—H25B	108.3
O3B—C3B—C2B	105.78 (14)	H25A—C25A—H25B	107.4
O3B—C3B—H3B	108.7	C26B—C25A—N20	116.1 (5)
O3B—C3B—C4B	112.19 (15)	C26B—C25A—H25A	108.3
C2B—C3B—H3B	108.7	C26B—C25A—H25B	108.3
C4B—C3B—C2B	112.70 (16)	H25C—C25B—H25D	107.3
C4B—C3B—H3B	108.7	C26A—C25B—H25C	108.1
O4B—C4B—N4B	123.89 (18)	C26A—C25B—H25D	108.1
O4B—C4B—C3B	119.71 (16)	C26A—C25B—N20A	116.7 (6)
N4B—C4B—C3B	116.36 (17)	N20A—C25B—H25C	108.1
O5B—C5B—N5B	124.45 (18)	N20A—C25B—H25D	108.1
O5B—C5B—C6B	119.45 (17)	C25B—C26A—H26D	109.5
N5B—C5B—C6B	116.10 (17)	C25B—C26A—H26E	109.5
O6B—C6B—C5B	112.74 (15)	C25B—C26A—H26F	109.5
O6B—C6B—H6B	109.0	H26D—C26A—H26E	109.5
O6B—C6B—C7B	105.44 (14)	H26D—C26A—H26F	109.5
C5B—C6B—H6B	109.0	H26E—C26A—H26F	109.5
C5B—C6B—C7B	111.40 (16)	C25A—C26B—H26A	109.5
C7B—C6B—H6B	109.0	C25A—C26B—H26B	109.5
O7B—C7B—C6B	105.96 (14)	C25A—C26B—H26C	109.5
O7B—C7B—H7B	109.1	H26A—C26B—H26B	109.5
O7B—C7B—C8B	111.87 (15)	H26A—C26B—H26C	109.5
C6B—C7B—H7B	109.1	H26B—C26B—H26C	109.5
C8B—C7B—C6B	111.60 (16)	H27C—C27A—H27D	107.4
C8B—C7B—H7B	109.1	C28A—C27A—H27C	108.2
O8B—C8B—N8B	123.60 (18)	C28A—C27A—H27D	108.2
O8B—C8B—C7B	119.57 (16)	N20A—C27A—H27C	108.2
N8B—C8B—C7B	116.83 (17)	N20A—C27A—H27D	108.2
H1WA—O1W—H1WB	104.5	N20A—C27A—C28A	116.4 (7)
H1XA—O1X—H1XB	104.5	C27A—C28A—H28D	109.5
H2WA—O2W—H2WB	104.5	C27A—C28A—H28E	109.5
H3WA—O3W—H3WB	103 (5)	C27A—C28A—H28F	109.5
H4WA—O4W—H4WB	114.8	H28D—C28A—H28E	109.5
H5WA—O5W—H5WB	125.7	H28D—C28A—H28F	109.5
H6WA—O6W—H6WB	104.5	H28E—C28A—H28F	109.5
H7WA—O7W—H7WB	105.1	N20—C27B—H27A	108.5
H7XA—O7X—H7XB	104.4	N20—C27B—H27B	108.5
H8WA—O8W—H8WB	96.2	C28B—C27B—N20	115.1 (5)
H8XA—O8X—H8XB	104.5	C28B—C27B—H27A	108.5
H9WA—O9W—H9WB	114.3	C28B—C27B—H27B	108.5
H9XA—O9X—H9XB	109.5	H27A—C27B—H27B	107.5
H10A—O10W—H10B	113.9	C23B—N20A—C25B	111.3 (5)
H11C—O11W—H11D	104.5	C23B—N20A—C21A	104.7 (7)
H12D—O12W—H12E	96.6	C25B—N20A—C21A	112.1 (7)
H12F—O12X—H12G	104.5	C27A—N20A—C23B	111.7 (6)
H13C—O13W—H13D	115.6	C27A—N20A—C25B	106.8 (6)
C11—N10—C13	111.06 (19)	C27A—N20A—C21A	110.3 (7)
C11—N10—C15	106.01 (19)	C22—C21A—H21C	109.7
C11—N10—C17	110.77 (17)	C22—C21A—H21D	109.7
C13—N10—C15	111.5 (2)	N20A—C21A—C22	109.7 (13)
C17—N10—C13	106.16 (19)	N20A—C21A—H21C	109.7
C17—N10—C15	111.4 (2)	N20A—C21A—H21D	109.7
N10—C11—H11A	108.5	H21C—C21A—H21D	108.2
N10—C11—H11B	108.5	C21—C22A—H22A	109.5
N10—C11—C12	115.2 (2)	C21—C22A—H22B	109.5
H11A—C11—H11B	107.5	C21—C22A—H22C	109.5
C12—C11—H11A	108.5	H22A—C22A—H22B	109.5
C12—C11—H11B	108.5	H22A—C22A—H22C	109.5
C11—C12—H12A	109.5	H22B—C22A—H22C	109.5
C11—C12—H12B	109.5	H3XA—O3X—H3XB	104.4
C11—C12—H12C	109.5
B1—O2A—C2A—C1A	−109.72 (18)	O3B—C3B—C4B—O4B	171.91 (18)
B1—O2A—C2A—C3A	10.5 (2)	O3B—C3B—C4B—N4B	−10.1 (2)
B1—O3A—C3A—C2A	19.0 (2)	O5B—C5B—C6B—O6B	−176.32 (18)
B1—O3A—C3A—C4A	−104.18 (18)	O5B—C5B—C6B—C7B	65.4 (2)
B1—O6A—C6A—C5A	−117.45 (18)	O6B—B2—O2B—C2B	−120.11 (17)
B1—O6A—C6A—C7A	3.2 (2)	O6B—B2—O3B—C3B	108.58 (18)
B1—O7A—C7A—C6A	4.6 (2)	O6B—B2—O7B—C7B	−3.1 (2)
B1—O7A—C7A—C8A	−118.16 (18)	O6B—C6B—C7B—O7B	−6.2 (2)
O1A—C1A—C2A—O2A	179.75 (18)	O6B—C6B—C7B—C8B	115.84 (17)
O1A—C1A—C2A—C3A	62.6 (2)	O7B—B2—O2B—C2B	122.66 (18)
O2A—B1—O3A—C3A	−12.8 (2)	O7B—B2—O3B—C3B	−134.31 (16)
O2A—B1—O6A—C6A	−122.83 (17)	O7B—B2—O6B—C6B	−1.2 (2)
O2A—B1—O7A—C7A	117.29 (19)	O7B—C7B—C8B—O8B	−174.20 (17)
O2A—C2A—C3A—O3A	−18.0 (2)	O7B—C7B—C8B—N8B	5.6 (3)
O2A—C2A—C3A—C4A	104.90 (18)	N1B—C1B—C2B—O2B	0.9 (3)
O3A—B1—O2A—C2A	0.5 (2)	N1B—C1B—C2B—C3B	−116.6 (2)
O3A—B1—O6A—C6A	120.12 (18)	N5B—C5B—C6B—O6B	3.3 (3)
O3A—B1—O7A—C7A	−126.99 (17)	N5B—C5B—C6B—C7B	−115.0 (2)
O3A—C3A—C4A—O4A	164.73 (17)	C1B—C2B—C3B—O3B	109.56 (17)
O3A—C3A—C4A—N4A	−18.2 (2)	C1B—C2B—C3B—C4B	−127.50 (17)
O5A—C5A—C6A—O6A	−176.19 (18)	C2B—C3B—C4B—O4B	52.6 (2)
O5A—C5A—C6A—C7A	66.4 (2)	C2B—C3B—C4B—N4B	−129.40 (18)
O6A—B1—O2A—C2A	−123.20 (18)	C5B—C6B—C7B—O7B	116.46 (17)
O6A—B1—O3A—C3A	107.43 (19)	C5B—C6B—C7B—C8B	−121.54 (17)
O6A—B1—O7A—C7A	−2.8 (2)	C6B—C7B—C8B—O8B	67.3 (2)
O6A—C6A—C7A—O7A	−4.7 (2)	C6B—C7B—C8B—N8B	−112.9 (2)
O6A—C6A—C7A—C8A	118.16 (17)	C11—N10—C13—C14	55.5 (3)
O7A—B1—O2A—C2A	119.37 (18)	C11—N10—C15—C16	176.2 (2)
O7A—B1—O3A—C3A	−134.26 (16)	C11—N10—C17—C18	−57.1 (3)
O7A—B1—O6A—C6A	−0.5 (2)	C13—N10—C11—C12	61.0 (3)
O7A—C7A—C8A—O8A	−175.23 (18)	C13—N10—C15—C16	−62.8 (3)
O7A—C7A—C8A—N8A	3.2 (3)	C13—N10—C17—C18	−177.8 (2)
N1A—C1A—C2A—O2A	0.0 (3)	C15—N10—C11—C12	−177.7 (2)
N1A—C1A—C2A—C3A	−117.2 (2)	C15—N10—C13—C14	−62.5 (3)
N5A—C5A—C6A—O6A	4.8 (3)	C15—N10—C17—C18	60.7 (3)
N5A—C5A—C6A—C7A	−112.7 (2)	C17—N10—C11—C12	−56.7 (3)
C1A—C2A—C3A—O3A	103.91 (17)	C17—N10—C13—C14	176.0 (2)
C1A—C2A—C3A—C4A	−133.18 (17)	C17—N10—C15—C16	55.6 (3)
C2A—C3A—C4A—O4A	45.8 (2)	C21—N20—C23A—C24A	179.0 (6)
C2A—C3A—C4A—N4A	−137.15 (18)	C21—N20—C25A—C26B	−59.2 (8)
C5A—C6A—C7A—O7A	116.83 (17)	C21—N20—C27B—C28B	59.6 (8)
C5A—C6A—C7A—C8A	−120.31 (18)	C23A—N20—C21—C22A	179.3 (12)
C6A—C7A—C8A—O8A	65.7 (2)	C23A—N20—C25A—C26B	58.0 (7)
C6A—C7A—C8A—N8A	−115.8 (2)	C23A—N20—C27B—C28B	−59.4 (7)
B2—O2B—C2B—C1B	−115.18 (17)	C23B—N20A—C21A—C22	−177.5 (13)
B2—O2B—C2B—C3B	5.4 (2)	C24B—C23B—N20A—C25B	60.6 (8)
B2—O3B—C3B—C2B	15.38 (19)	C24B—C23B—N20A—C27A	−58.7 (8)
B2—O3B—C3B—C4B	−107.88 (17)	C24B—C23B—N20A—C21A	−178.1 (8)
B2—O6B—C6B—C5B	−117.32 (18)	C25A—N20—C21—C22A	−60.0 (13)
B2—O6B—C6B—C7B	4.4 (2)	C25A—N20—C23A—C24A	60.1 (7)
B2—O7B—C7B—C6B	5.7 (2)	C25A—N20—C27B—C28B	178.6 (6)
B2—O7B—C7B—C8B	−116.10 (18)	C25B—N20A—C21A—C22	−56.6 (15)
O1B—C1B—C2B—O2B	−179.47 (17)	C26A—C25B—N20A—C23B	60.6 (9)
O1B—C1B—C2B—C3B	63.0 (2)	C26A—C25B—N20A—C27A	−177.1 (7)
O2B—B2—O3B—C3B	−12.2 (2)	C26A—C25B—N20A—C21A	−56.3 (10)
O2B—B2—O6B—C6B	−123.84 (16)	C27A—N20A—C21A—C22	62.2 (15)
O2B—B2—O7B—C7B	117.22 (18)	C28A—C27A—N20A—C23B	−55.7 (9)
O2B—C2B—C3B—O3B	−12.66 (19)	C28A—C27A—N20A—C25B	−177.6 (7)
O2B—C2B—C3B—C4B	110.27 (17)	C28A—C27A—N20A—C21A	60.4 (10)
O3B—B2—O2B—C2B	3.5 (2)	C27B—N20—C21—C22A	57.3 (13)
O3B—B2—O6B—C6B	118.53 (18)	C27B—N20—C23A—C24A	−58.6 (7)
O3B—B2—O7B—C7B	−126.28 (17)	C27B—N20—C25A—C26B	179.8 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AB···O4B^i	0.89 (3)	1.99 (3)	2.850 (2)	161 (3)
N4A—H4AB···O8A^ii	0.88 (3)	2.07 (3)	2.923 (2)	166 (3)
N5A—H5AA···O6A	0.92 (3)	2.16 (3)	2.633 (2)	111 (2)
N5A—H5AB···O8A^iii	0.85 (3)	2.03 (3)	2.867 (2)	168 (3)
N8A—H8AA···O4A^iv	0.87 (3)	2.04 (3)	2.898 (2)	166 (3)
N1B—H1BA···O4A^v	0.86 (3)	2.02 (3)	2.874 (2)	170 (3)
N4B—H4BA···O8B^iv	0.88 (3)	2.05 (3)	2.915 (2)	165 (2)
N5B—H5BA···O8B^vi	0.86 (3)	2.01 (3)	2.860 (2)	168 (2)
N8B—H8BB···O4B^ii	0.88 (3)	2.02 (3)	2.870 (2)	162 (3)
O1W—H1WA···O2B	0.87	1.94	2.798 (2)	167
O1W—H1WB···O5W^iv	0.87	1.90	2.769 (3)	177
O1X—H1XA···O2B	0.87	2.17	2.843 (17)	134
O2W—H2WA···O1W	0.87	1.90	2.739 (3)	163
O2W—H2WA···O1X	0.87	1.94	2.752 (16)	154
O2W—H2WB···O1A^v	0.87	2.01	2.872 (3)	173
O3W—H3WA···O2W	0.84 (4)	1.94 (4)	2.785 (3)	178 (4)
O3W—H3WB···O4W	0.78 (5)	2.10 (4)	2.836 (3)	158 (5)
O4W—H4WA···O1B^i	0.88	1.93	2.798 (2)	171
O4W—H4WB···O5W	0.87	1.96	2.791 (2)	158
O5W—H5WA···O6W	0.87	1.89	2.763 (3)	175
O5W—H5WB···O2A	0.89	1.89	2.775 (2)	175
O6W—H6WA···O6B^ii	0.87	2.02	2.858 (2)	163
O6W—H6WB···O7W	0.87	1.85	2.711 (4)	168
O6W—H6WB···O7X	0.87	2.10	2.897 (10)	152
O7W—H7WA···O8W	0.87	1.93	2.765 (5)	162
O7W—H7WB···O13W^ii	0.89	1.89	2.739 (4)	159
O8W—H8WA···O5A	0.87	1.98	2.791 (5)	156
O8W—H8WB···O9W	0.88	1.86	2.731 (4)	169
O8X—H8XB···O7X	0.87	1.88	2.735 (13)	165
O9W—H9WA···O10W	0.76	2.16	2.868 (3)	154
O9W—H9WB···O3A^vii	0.90	1.94	2.815 (3)	162
O9X—H9XA···O11W	0.87	1.69	2.366 (9)	132
O10W—H10A···O7B^viii	0.87	1.96	2.826 (2)	171
O10W—H10B···O3W^ix	0.94	1.88	2.788 (3)	163
O10W—H10B···O3X^ix	0.94	2.26	3.16 (3)	159
O11W—H11C···O3W^ix	0.87	2.04	2.861 (3)	157
O11W—H11D···O7A^vii	0.87	1.92	2.776 (3)	168
O12W—H12D···O3B^viii	0.87	1.97	2.783 (5)	156
O12W—H12E···O11W	0.83	2.09	2.862 (5)	154
O12X—H12F···O9X	0.87	2.13	2.88 (2)	143
O13W—H13C···O12W	0.87	1.92	2.782 (5)	173
O13W—H13C···O12X	0.87	1.81	2.658 (19)	165
O13W—H13D···O5B	0.79	2.09	2.858 (3)	167

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y, z; (iii) x+1/2, −y+3/2, −z+1; (iv) x−1, y, z; (v) −x+2, y−1/2, −z+1/2; (vi) x−1/2, −y+1/2, −z+1; (vii) x−1/2, −y+3/2, −z+1; (viii) x+1/2, −y+1/2, −z+1; (ix) −x+3/2, −y+1, z+1/2.

Tetrabutylazanium 2,3,7,8-tetracarboxamido-1,4,6,9-tetraoxa-5λ⁴-boraspiro[4.4]nonane ethanol monosolvate hemihydrate (aris36a)

Crystal data

C16H36N^+·C8H12BN4O8^−·C2H6O·0.5H2O	F(000) = 654
Mr = 600.56	Dx = 1.221 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 11.49802 (16) Å	Cell parameters from 6430 reflections
b = 10.19256 (10) Å	θ = 4.3–75.5°
c = 14.65365 (18) Å	µ = 0.76 mm^−1
β = 107.9163 (14)°	T = 100 K
V = 1634.04 (4) Å^3	Needle, colourless
Z = 2	0.3 × 0.1 × 0.05 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	5805 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	5518 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.022
Detector resolution: 10.3577 pixels mm^-1	θmax = 67.5°, θmin = 4.0°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −12→12
Tmin = 0.698, Tmax = 1.000	l = −12→17
9081 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.0305P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.072	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.18 e Å^−3
5805 reflections	Δρmin = −0.16 e Å^−3
474 parameters	Absolute structure: Flack x determined using 2452 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
33 restraints	Absolute structure parameter: −0.03 (7)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N10	0.65245 (15)	0.56698 (18)	0.25628 (12)	0.0212 (3)
C11	0.72929 (18)	0.4685 (2)	0.32806 (14)	0.0219 (4)
H11A	0.8054	0.4515	0.3118	0.026*
H11B	0.7528	0.5088	0.3927	0.026*
C12	0.66705 (19)	0.3377 (2)	0.33232 (15)	0.0252 (4)
H12A	0.6657	0.2841	0.2757	0.030*
H12B	0.5815	0.3533	0.3309	0.030*
C13	0.7351 (2)	0.2638 (2)	0.42378 (17)	0.0299 (5)
H13A	0.8229	0.2590	0.4291	0.036*
H13B	0.7277	0.3130	0.4800	0.036*
C14	0.6859 (2)	0.1252 (3)	0.42554 (19)	0.0364 (5)
H14A	0.6972	0.0745	0.3721	0.055*
H14B	0.5986	0.1293	0.4194	0.055*
H14C	0.7301	0.0827	0.4863	0.055*
C15	0.73924 (18)	0.6768 (2)	0.25030 (15)	0.0222 (4)
H15A	0.7828	0.7064	0.3163	0.027*
H15B	0.8012	0.6402	0.2231	0.027*
C16	0.6825 (2)	0.7956 (2)	0.19165 (16)	0.0279 (4)
H16A	0.6199	0.8341	0.2174	0.034*
H16B	0.6419	0.7693	0.1243	0.034*
C17	0.7823 (2)	0.8973 (2)	0.19576 (19)	0.0355 (5)
H17A	0.8249	0.9191	0.2637	0.043*
H17B	0.8430	0.8581	0.1684	0.043*
C18	0.7334 (3)	1.0224 (3)	0.1420 (2)	0.0475 (7)
H18A	0.6980	1.0029	0.0735	0.071*
H18B	0.8002	1.0856	0.1511	0.071*
H18C	0.6703	1.0596	0.1666	0.071*
C21	0.59525 (18)	0.5035 (2)	0.15911 (14)	0.0227 (4)
H21A	0.5470	0.5709	0.1147	0.027*
H21B	0.5375	0.4351	0.1661	0.027*
C22	0.68395 (19)	0.4412 (2)	0.11307 (15)	0.0247 (4)
H22A	0.7425	0.3843	0.1601	0.030*
H22B	0.7308	0.5104	0.0923	0.030*
C23	0.6116 (2)	0.3602 (3)	0.02668 (17)	0.0340 (5)
H23A	0.5690	0.2882	0.0489	0.041*
H23B	0.5486	0.4165	−0.0171	0.041*
C24	0.6921 (2)	0.3020 (3)	−0.02810 (18)	0.0419 (6)
H24A	0.6428	0.2453	−0.0795	0.063*
H24B	0.7576	0.2502	0.0158	0.063*
H24C	0.7280	0.3729	−0.0559	0.063*
C25	0.54636 (19)	0.6172 (2)	0.28852 (15)	0.0258 (4)
H25A	0.4945	0.5416	0.2932	0.031*
H25B	0.4960	0.6767	0.2384	0.031*
C26	0.5830 (2)	0.6902 (3)	0.38425 (17)	0.0328 (5)
H26A	0.6411	0.7617	0.3839	0.039*	0.5
H26B	0.6222	0.6294	0.4375	0.039*	0.5
H26C	0.6507	0.7511	0.3860	0.039*	0.5
H26D	0.6141	0.6257	0.4367	0.039*	0.5
C27	0.4645 (13)	0.7462 (14)	0.3959 (11)	0.039 (2)	0.5
H27A	0.4001	0.6782	0.3772	0.046*	0.5
H27B	0.4783	0.7671	0.4644	0.046*	0.5
C27A	0.4782 (14)	0.7686 (13)	0.4029 (13)	0.043 (2)	0.5
H27C	0.4436	0.8291	0.3485	0.051*	0.5
H27D	0.4127	0.7069	0.4053	0.051*	0.5
C28	0.4199 (5)	0.8670 (6)	0.3375 (5)	0.0473 (12)	0.5
H28A	0.4884	0.9276	0.3449	0.071*	0.5
H28B	0.3571	0.9096	0.3596	0.071*	0.5
H28C	0.3852	0.8429	0.2698	0.071*	0.5
C28A	0.5158 (6)	0.8457 (6)	0.4931 (5)	0.0457 (13)	0.5
H28D	0.5822	0.9055	0.4923	0.069*	0.5
H28E	0.5441	0.7860	0.5479	0.069*	0.5
H28F	0.4460	0.8966	0.4988	0.069*	0.5
O1	0.14217 (14)	0.01723 (14)	0.39066 (10)	0.0222 (3)
O2	−0.01405 (12)	0.29328 (13)	0.25524 (9)	0.0180 (3)
O3	0.14046 (12)	0.41343 (13)	0.36320 (9)	0.0181 (3)
O4	0.05353 (13)	0.24862 (13)	0.54781 (9)	0.0203 (3)
O5	0.14946 (14)	0.80402 (14)	0.18672 (10)	0.0234 (3)
O6	−0.01563 (12)	0.53039 (13)	0.23869 (9)	0.0175 (3)
O7	0.13210 (12)	0.41300 (13)	0.19431 (9)	0.0181 (3)
O8	0.0126 (2)	0.58676 (15)	−0.02733 (11)	0.0386 (4)
N1	0.09808 (18)	0.06705 (17)	0.23303 (12)	0.0221 (4)
H1A	0.058 (3)	0.122 (3)	0.187 (2)	0.026 (6)*
H1B	0.131 (3)	−0.006 (3)	0.218 (2)	0.032 (7)*
N4	0.01870 (16)	0.45694 (16)	0.49116 (12)	0.0194 (3)
H4A	−0.026 (3)	0.478 (3)	0.527 (2)	0.026 (7)*
H4B	0.030 (2)	0.515 (3)	0.452 (2)	0.027 (7)*
N5	0.10008 (17)	0.75224 (18)	0.32011 (12)	0.0201 (3)
H5A	0.057 (3)	0.700 (3)	0.3404 (19)	0.022 (6)*
H5B	0.131 (2)	0.824 (3)	0.3477 (19)	0.021 (6)*
N8	0.00155 (19)	0.37260 (17)	0.00910 (13)	0.0253 (4)
H8A	0.018 (3)	0.315 (3)	0.052 (2)	0.033 (7)*
H8B	−0.046 (3)	0.350 (3)	−0.049 (2)	0.041 (8)*
C1	0.09620 (18)	0.09081 (18)	0.32134 (13)	0.0174 (4)
C2	0.03092 (18)	0.21471 (18)	0.33684 (13)	0.0164 (4)
H2	−0.0388	0.1891	0.3604	0.020*
C3	0.12027 (17)	0.30345 (18)	0.41401 (12)	0.0154 (3)
H3	0.1991	0.2559	0.4430	0.018*
C4	0.06217 (17)	0.33569 (18)	0.49197 (12)	0.0156 (3)
C5	0.09937 (18)	0.73079 (17)	0.23117 (13)	0.0158 (4)
C6	0.02689 (18)	0.61312 (18)	0.17918 (13)	0.0165 (4)
H6	−0.0450	0.6459	0.1263	0.020*
C7	0.10537 (18)	0.52482 (18)	0.13503 (13)	0.0169 (4)
H7	0.1831	0.5713	0.1382	0.020*
C8	0.0347 (2)	0.49537 (19)	0.03048 (14)	0.0209 (4)
B1	0.06068 (19)	0.4119 (2)	0.26337 (14)	0.0158 (4)
O2S	0.3467 (7)	0.3150 (8)	0.1746 (7)	0.0457 (19)	0.3333
H2S	0.2790	0.3422	0.1776	0.069*	0.3333
C3S	0.3323 (10)	0.1838 (11)	0.1344 (9)	0.041 (2)	0.3333
H3SA	0.3657	0.1801	0.0798	0.049*	0.3333
H3SB	0.2444	0.1608	0.1105	0.049*	0.3333
C4S	0.3992 (8)	0.0869 (10)	0.2108 (8)	0.054 (2)	0.3333
H4SA	0.3770	−0.0027	0.1877	0.081*	0.3333
H4SB	0.3763	0.1017	0.2692	0.081*	0.3333
H4SC	0.4876	0.0990	0.2251	0.081*	0.3333
O1S	0.3675 (3)	0.3351 (4)	0.2213 (3)	0.0384 (8)	0.6667
H1S	0.2984	0.3521	0.2268	0.058*	0.6667
C1S	0.3682 (5)	0.2054 (5)	0.1876 (6)	0.0512 (14)	0.6667
H1SA	0.3260	0.1475	0.2216	0.061*	0.6667
H1SB	0.4539	0.1750	0.2031	0.061*	0.6667
C2S	0.3084 (6)	0.1935 (10)	0.0837 (6)	0.085 (3)	0.6667
H2SA	0.2202	0.2065	0.0695	0.127*	0.6667
H2SB	0.3239	0.1059	0.0624	0.127*	0.6667
H2SC	0.3414	0.2600	0.0501	0.127*	0.6667
O1W	0.3954 (13)	0.4260 (14)	0.3960 (10)	0.053 (3)	0.25
H1WA	0.4084	0.3981	0.3464	0.080*	0.25
H1WB	0.3254	0.4232	0.3950	0.080*	0.25
O2W	0.3915 (14)	0.3801 (14)	0.3745 (11)	0.060 (4)	0.25
H2WA	0.3712	0.3664	0.3166	0.090*	0.25
H2WB	0.3267	0.3935	0.3877	0.090*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N10	0.0173 (8)	0.0258 (8)	0.0197 (8)	0.0009 (7)	0.0044 (6)	−0.0012 (7)
C11	0.0182 (9)	0.0271 (10)	0.0184 (9)	0.0021 (8)	0.0025 (7)	0.0000 (8)
C12	0.0216 (9)	0.0293 (11)	0.0228 (9)	−0.0004 (8)	0.0039 (8)	0.0029 (8)
C13	0.0243 (11)	0.0327 (13)	0.0301 (11)	−0.0003 (9)	0.0045 (9)	0.0079 (9)
C14	0.0356 (12)	0.0330 (12)	0.0398 (13)	0.0004 (10)	0.0106 (10)	0.0086 (10)
C15	0.0187 (10)	0.0240 (10)	0.0222 (10)	−0.0003 (8)	0.0038 (8)	−0.0023 (8)
C16	0.0230 (10)	0.0276 (10)	0.0319 (11)	0.0019 (9)	0.0066 (8)	0.0026 (9)
C17	0.0268 (11)	0.0288 (12)	0.0483 (14)	−0.0006 (9)	0.0076 (10)	0.0063 (11)
C18	0.0398 (14)	0.0311 (13)	0.0662 (18)	−0.0018 (11)	0.0085 (13)	0.0125 (13)
C21	0.0186 (9)	0.0285 (11)	0.0178 (9)	−0.0006 (8)	0.0009 (7)	0.0003 (8)
C22	0.0232 (10)	0.0287 (11)	0.0209 (9)	−0.0014 (8)	0.0050 (8)	−0.0023 (8)
C23	0.0281 (11)	0.0469 (14)	0.0261 (11)	−0.0072 (10)	0.0074 (9)	−0.0101 (10)
C24	0.0394 (13)	0.0561 (16)	0.0311 (12)	−0.0065 (12)	0.0124 (10)	−0.0169 (12)
C25	0.0191 (9)	0.0331 (11)	0.0269 (10)	0.0055 (9)	0.0097 (8)	0.0019 (9)
C26	0.0325 (12)	0.0393 (13)	0.0295 (11)	0.0063 (9)	0.0140 (9)	−0.0032 (9)
C27	0.035 (3)	0.046 (4)	0.038 (4)	0.005 (3)	0.016 (2)	−0.014 (3)
C27A	0.044 (3)	0.039 (4)	0.055 (4)	0.009 (3)	0.029 (3)	−0.004 (3)
C28	0.038 (3)	0.046 (3)	0.056 (3)	0.005 (2)	0.012 (2)	−0.011 (2)
C28A	0.056 (3)	0.036 (3)	0.064 (3)	−0.012 (2)	0.047 (3)	−0.013 (2)
O1	0.0371 (8)	0.0139 (6)	0.0165 (6)	0.0008 (6)	0.0095 (6)	0.0006 (5)
O2	0.0239 (7)	0.0127 (6)	0.0148 (6)	−0.0013 (5)	0.0023 (5)	0.0007 (5)
O3	0.0251 (6)	0.0147 (6)	0.0149 (6)	−0.0069 (5)	0.0065 (5)	0.0004 (5)
O4	0.0281 (7)	0.0176 (6)	0.0160 (6)	0.0014 (5)	0.0079 (5)	0.0032 (5)
O5	0.0392 (8)	0.0150 (7)	0.0204 (7)	−0.0034 (6)	0.0156 (6)	−0.0018 (5)
O6	0.0218 (6)	0.0118 (6)	0.0215 (7)	0.0013 (5)	0.0106 (5)	0.0000 (5)
O7	0.0257 (7)	0.0147 (6)	0.0162 (6)	0.0062 (5)	0.0100 (5)	0.0024 (5)
O8	0.0801 (13)	0.0146 (7)	0.0161 (7)	0.0024 (7)	0.0073 (8)	0.0015 (6)
N1	0.0379 (10)	0.0137 (8)	0.0167 (8)	0.0007 (7)	0.0115 (7)	0.0005 (6)
N4	0.0273 (9)	0.0139 (8)	0.0187 (8)	0.0011 (6)	0.0095 (7)	−0.0011 (6)
N5	0.0330 (9)	0.0133 (7)	0.0158 (8)	−0.0039 (7)	0.0101 (7)	−0.0011 (6)
N8	0.0406 (10)	0.0132 (8)	0.0182 (8)	−0.0009 (7)	0.0035 (8)	0.0004 (7)
C1	0.0251 (10)	0.0123 (9)	0.0166 (9)	−0.0059 (7)	0.0089 (7)	−0.0018 (7)
C2	0.0224 (9)	0.0127 (9)	0.0146 (8)	−0.0037 (7)	0.0063 (7)	−0.0014 (7)
C3	0.0204 (9)	0.0119 (8)	0.0140 (8)	−0.0023 (7)	0.0057 (7)	−0.0015 (7)
C4	0.0185 (8)	0.0142 (8)	0.0122 (8)	−0.0010 (7)	0.0019 (7)	−0.0021 (7)
C5	0.0238 (10)	0.0102 (9)	0.0144 (9)	0.0044 (7)	0.0073 (7)	0.0012 (6)
C6	0.0232 (9)	0.0116 (8)	0.0153 (8)	0.0030 (7)	0.0069 (7)	0.0012 (7)
C7	0.0259 (9)	0.0111 (8)	0.0154 (8)	0.0018 (7)	0.0089 (7)	0.0007 (7)
C8	0.0343 (11)	0.0123 (9)	0.0175 (9)	0.0039 (8)	0.0099 (8)	−0.0003 (7)
B1	0.0210 (10)	0.0132 (9)	0.0141 (9)	0.0010 (8)	0.0069 (8)	−0.0015 (8)
O2S	0.029 (4)	0.044 (4)	0.067 (5)	0.004 (3)	0.019 (4)	−0.011 (4)
C3S	0.022 (6)	0.056 (6)	0.041 (6)	−0.007 (4)	0.006 (5)	−0.016 (6)
C4S	0.038 (4)	0.041 (5)	0.071 (6)	−0.002 (4)	−0.002 (4)	−0.014 (4)
O1S	0.0225 (15)	0.0384 (18)	0.054 (2)	0.0029 (12)	0.0119 (17)	−0.0096 (18)
C1S	0.025 (2)	0.028 (2)	0.100 (5)	0.0020 (18)	0.018 (3)	−0.002 (3)
C2S	0.040 (3)	0.130 (7)	0.083 (5)	−0.002 (4)	0.017 (4)	−0.062 (6)
O1W	0.038 (4)	0.064 (6)	0.062 (6)	−0.006 (4)	0.021 (4)	0.010 (5)
O2W	0.044 (5)	0.070 (6)	0.068 (6)	−0.003 (5)	0.021 (4)	−0.003 (5)

Geometric parameters (Å, º)

N10—C11	1.524 (3)	C28A—H28D	0.9800
N10—C15	1.520 (3)	C28A—H28E	0.9800
N10—C21	1.517 (3)	C28A—H28F	0.9800
N10—C25	1.526 (2)	O1—C1	1.242 (3)
C11—H11A	0.9900	O2—C2	1.399 (2)
C11—H11B	0.9900	O2—B1	1.467 (2)
C11—C12	1.523 (3)	O3—C3	1.404 (2)
C12—H12A	0.9900	O3—B1	1.468 (2)
C12—H12B	0.9900	O4—C4	1.232 (2)
C12—C13	1.527 (3)	O5—C5	1.243 (2)
C13—H13A	0.9900	O6—C6	1.405 (2)
C13—H13B	0.9900	O6—B1	1.471 (2)
C13—C14	1.525 (3)	O7—C7	1.409 (2)
C14—H14A	0.9800	O7—B1	1.487 (2)
C14—H14B	0.9800	O8—C8	1.232 (3)
C14—H14C	0.9800	N1—H1A	0.89 (3)
C15—H15A	0.9900	N1—H1B	0.89 (3)
C15—H15B	0.9900	N1—C1	1.323 (3)
C15—C16	1.511 (3)	N4—H4A	0.87 (3)
C16—H16A	0.9900	N4—H4B	0.87 (3)
C16—H16B	0.9900	N4—C4	1.332 (3)
C16—C17	1.534 (3)	N5—H5A	0.84 (3)
C17—H17A	0.9900	N5—H5B	0.86 (3)
C17—H17B	0.9900	N5—C5	1.319 (3)
C17—C18	1.513 (3)	N8—H8A	0.84 (3)
C18—H18A	0.9800	N8—H8B	0.89 (3)
C18—H18B	0.9800	N8—C8	1.317 (3)
C18—H18C	0.9800	C1—C2	1.521 (3)
C21—H21A	0.9900	C2—H2	1.0000
C21—H21B	0.9900	C2—C3	1.561 (2)
C21—C22	1.524 (3)	C3—H3	1.0000
C22—H22A	0.9900	C3—C4	1.526 (2)
C22—H22B	0.9900	C5—C6	1.524 (3)
C22—C23	1.526 (3)	C6—H6	1.0000
C23—H23A	0.9900	C6—C7	1.550 (2)
C23—H23B	0.9900	C7—H7	1.0000
C23—C24	1.521 (3)	C7—C8	1.527 (3)
C24—H24A	0.9800	O2S—H2S	0.8400
C24—H24B	0.9800	O2S—C3S	1.450 (13)
C24—H24C	0.9800	C3S—H3SA	0.9900
C25—H25A	0.9900	C3S—H3SB	0.9900
C25—H25B	0.9900	C3S—C4S	1.514 (16)
C25—C26	1.528 (3)	C4S—H4SA	0.9800
C26—H26A	0.9900	C4S—H4SB	0.9800
C26—H26B	0.9900	C4S—H4SC	0.9800
C26—H26C	0.9900	O1S—H1S	0.8400
C26—H26D	0.9900	O1S—C1S	1.412 (7)
C26—C27	1.534 (14)	C1S—H1SA	0.9900
C26—C27A	1.539 (14)	C1S—H1SB	0.9900
C27—H27A	0.9900	C1S—C2S	1.470 (10)
C27—H27B	0.9900	C2S—H2SA	0.9800
C27—C28	1.497 (18)	C2S—H2SB	0.9800
C27A—H27C	0.9900	C2S—H2SC	0.9800
C27A—H27D	0.9900	O1W—H1WA	0.8357
C27A—C28A	1.483 (17)	O1W—H1WB	0.8018
C28—H28A	0.9800	O2W—H2WA	0.8199
C28—H28B	0.9800	O2W—H2WB	0.8370
C28—H28C	0.9800
C11—N10—C25	110.88 (15)	C26—C27A—H27D	108.8
C15—N10—C11	105.86 (15)	H27C—C27A—H27D	107.7
C15—N10—C25	111.85 (16)	C28A—C27A—C26	113.8 (11)
C21—N10—C11	111.03 (16)	C28A—C27A—H27C	108.8
C21—N10—C15	111.26 (15)	C28A—C27A—H27D	108.8
C21—N10—C25	106.06 (15)	C27—C28—H28A	109.5
N10—C11—H11A	108.5	C27—C28—H28B	109.5
N10—C11—H11B	108.5	C27—C28—H28C	109.5
H11A—C11—H11B	107.5	H28A—C28—H28B	109.5
C12—C11—N10	115.13 (16)	H28A—C28—H28C	109.5
C12—C11—H11A	108.5	H28B—C28—H28C	109.5
C12—C11—H11B	108.5	C27A—C28A—H28D	109.5
C11—C12—H12A	109.6	C27A—C28A—H28E	109.5
C11—C12—H12B	109.6	C27A—C28A—H28F	109.5
C11—C12—C13	110.34 (18)	H28D—C28A—H28E	109.5
H12A—C12—H12B	108.1	H28D—C28A—H28F	109.5
C13—C12—H12A	109.6	H28E—C28A—H28F	109.5
C13—C12—H12B	109.6	C2—O2—B1	110.43 (14)
C12—C13—H13A	109.1	C3—O3—B1	111.42 (14)
C12—C13—H13B	109.1	C6—O6—B1	110.51 (14)
H13A—C13—H13B	107.9	C7—O7—B1	111.39 (14)
C14—C13—C12	112.3 (2)	H1A—N1—H1B	120 (2)
C14—C13—H13A	109.1	C1—N1—H1A	117.6 (18)
C14—C13—H13B	109.1	C1—N1—H1B	122.1 (19)
C13—C14—H14A	109.5	H4A—N4—H4B	118 (3)
C13—C14—H14B	109.5	C4—N4—H4A	121.2 (19)
C13—C14—H14C	109.5	C4—N4—H4B	120.4 (18)
H14A—C14—H14B	109.5	H5A—N5—H5B	125 (2)
H14A—C14—H14C	109.5	C5—N5—H5A	114.6 (18)
H14B—C14—H14C	109.5	C5—N5—H5B	119.0 (17)
N10—C15—H15A	108.2	H8A—N8—H8B	118 (3)
N10—C15—H15B	108.2	C8—N8—H8A	120 (2)
H15A—C15—H15B	107.3	C8—N8—H8B	122 (2)
C16—C15—N10	116.49 (17)	O1—C1—N1	123.94 (19)
C16—C15—H15A	108.2	O1—C1—C2	118.98 (16)
C16—C15—H15B	108.2	N1—C1—C2	117.07 (17)
C15—C16—H16A	109.8	O2—C2—C1	114.65 (15)
C15—C16—H16B	109.8	O2—C2—H2	108.6
C15—C16—C17	109.38 (18)	O2—C2—C3	105.98 (14)
H16A—C16—H16B	108.2	C1—C2—H2	108.6
C17—C16—H16A	109.8	C1—C2—C3	110.12 (16)
C17—C16—H16B	109.8	C3—C2—H2	108.6
C16—C17—H17A	108.9	O3—C3—C2	104.93 (14)
C16—C17—H17B	108.9	O3—C3—H3	109.6
H17A—C17—H17B	107.7	O3—C3—C4	114.01 (15)
C18—C17—C16	113.3 (2)	C2—C3—H3	109.6
C18—C17—H17A	108.9	C4—C3—C2	108.96 (14)
C18—C17—H17B	108.9	C4—C3—H3	109.6
C17—C18—H18A	109.5	O4—C4—N4	124.60 (17)
C17—C18—H18B	109.5	O4—C4—C3	119.05 (16)
C17—C18—H18C	109.5	N4—C4—C3	116.27 (17)
H18A—C18—H18B	109.5	O5—C5—N5	123.74 (18)
H18A—C18—H18C	109.5	O5—C5—C6	118.75 (16)
H18B—C18—H18C	109.5	N5—C5—C6	117.43 (17)
N10—C21—H21A	108.3	O6—C6—C5	113.78 (15)
N10—C21—H21B	108.3	O6—C6—H6	108.6
N10—C21—C22	115.92 (16)	O6—C6—C7	105.61 (15)
H21A—C21—H21B	107.4	C5—C6—H6	108.6
C22—C21—H21A	108.3	C5—C6—C7	111.50 (15)
C22—C21—H21B	108.3	C7—C6—H6	108.6
C21—C22—H22A	109.9	O7—C7—C6	104.89 (14)
C21—C22—H22B	109.9	O7—C7—H7	109.4
C21—C22—C23	108.92 (17)	O7—C7—C8	114.05 (15)
H22A—C22—H22B	108.3	C6—C7—H7	109.4
C23—C22—H22A	109.9	C8—C7—C6	109.53 (16)
C23—C22—H22B	109.9	C8—C7—H7	109.4
C22—C23—H23A	109.1	O8—C8—N8	124.84 (19)
C22—C23—H23B	109.1	O8—C8—C7	118.35 (18)
H23A—C23—H23B	107.8	N8—C8—C7	116.81 (18)
C24—C23—C22	112.56 (19)	O2—B1—O3	105.11 (15)
C24—C23—H23A	109.1	O2—B1—O6	111.51 (15)
C24—C23—H23B	109.1	O2—B1—O7	112.56 (15)
C23—C24—H24A	109.5	O3—B1—O6	112.25 (15)
C23—C24—H24B	109.5	O3—B1—O7	111.81 (15)
C23—C24—H24C	109.5	O6—B1—O7	103.82 (15)
H24A—C24—H24B	109.5	C3S—O2S—H2S	109.5
H24A—C24—H24C	109.5	O2S—C3S—H3SA	109.8
H24B—C24—H24C	109.5	O2S—C3S—H3SB	109.8
N10—C25—H25A	108.5	O2S—C3S—C4S	109.4 (10)
N10—C25—H25B	108.5	H3SA—C3S—H3SB	108.2
N10—C25—C26	115.26 (17)	C4S—C3S—H3SA	109.8
H25A—C25—H25B	107.5	C4S—C3S—H3SB	109.8
C26—C25—H25A	108.5	C3S—C4S—H4SA	109.5
C26—C25—H25B	108.5	C3S—C4S—H4SB	109.5
C25—C26—H26A	110.5	C3S—C4S—H4SC	109.5
C25—C26—H26B	110.5	H4SA—C4S—H4SB	109.5
C25—C26—H26C	108.8	H4SA—C4S—H4SC	109.5
C25—C26—H26D	108.8	H4SB—C4S—H4SC	109.5
C25—C26—C27	106.3 (5)	C1S—O1S—H1S	109.5
C25—C26—C27A	114.0 (7)	O1S—C1S—H1SA	109.0
H26A—C26—H26B	108.7	O1S—C1S—H1SB	109.0
H26C—C26—H26D	107.7	O1S—C1S—C2S	112.8 (6)
C27—C26—H26A	110.5	H1SA—C1S—H1SB	107.8
C27—C26—H26B	110.5	C2S—C1S—H1SA	109.0
C27A—C26—H26C	108.8	C2S—C1S—H1SB	109.0
C27A—C26—H26D	108.8	C1S—C2S—H2SA	109.5
C26—C27—H27A	108.8	C1S—C2S—H2SB	109.5
C26—C27—H27B	108.8	C1S—C2S—H2SC	109.5
H27A—C27—H27B	107.7	H2SA—C2S—H2SB	109.5
C28—C27—C26	113.7 (11)	H2SA—C2S—H2SC	109.5
C28—C27—H27A	108.8	H2SB—C2S—H2SC	109.5
C28—C27—H27B	108.8	H1WA—O1W—H1WB	114.8
C26—C27A—H27C	108.8	H2WA—O2W—H2WB	106.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.89 (3)	2.29 (3)	2.710 (2)	109 (2)
N1—H1B···O5^i	0.89 (3)	2.02 (3)	2.871 (2)	160 (3)
N4—H4A···O1^ii	0.87 (3)	2.09 (3)	2.961 (2)	175 (3)
N4—H4B···O3	0.87 (3)	2.32 (3)	2.699 (2)	107 (2)
N5—H5A···O6	0.84 (3)	2.26 (3)	2.707 (2)	113 (2)
N5—H5B···O1^iii	0.86 (3)	2.06 (3)	2.879 (2)	160 (2)
N8—H8A···O7	0.84 (3)	2.32 (3)	2.699 (2)	108 (2)
N8—H8B···O5^iv	0.89 (3)	2.05 (4)	2.945 (2)	177 (3)
O2S—H2S···O7	0.84	1.92	2.759 (8)	175
O1S—H1S···O7	0.84	1.93	2.730 (4)	160
O1W—H1WA···O1S	0.84	1.86	2.647 (15)	156
O1W—H1WB···O3	0.80	2.03	2.824 (14)	168
O2W—H2WA···O2S	0.82	2.08	2.892 (18)	171
O2W—H2WB···O3	0.84	2.07	2.860 (16)	158

Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1; (iii) x, y+1, z; (iv) −x, y−1/2, −z.

7-Aza-15-azoniatetracyclo[7.7.1.0^2,7.0^10,15]heptadecane 2,3,7,8-tetracarboxamido-1,4,6,9-tetraoxa-5λ⁴-boraspiro[4.4]nonane ethanol monosolvate (aris52cult)

Crystal data

C15H27N2^+·C8H12BN4O8^−·C2H6O	Dx = 1.346 Mg m^−3
Mr = 584.48	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 12885 reflections
a = 10.41666 (15) Å	θ = 3.8–75.4°
b = 15.3809 (2) Å	µ = 0.85 mm^−1
c = 18.0053 (3) Å	T = 100 K
V = 2884.76 (7) Å^3	Block, colourless
Z = 4	0.15 × 0.1 × 0.08 mm
F(000) = 1256

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	5201 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	4990 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.022
Detector resolution: 10.3577 pixels mm^-1	θmax = 67.5°, θmin = 3.8°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −18→18
Tmin = 0.900, Tmax = 1.000	l = −20→21
19437 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.0408P)^2 + 0.3459P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.068	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.24 e Å^−3
5201 reflections	Δρmin = −0.17 e Å^−3
411 parameters	Absolute structure: Flack x determined using 2133 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.02 (5)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
B1	0.52523 (18)	0.50202 (13)	0.51628 (11)	0.0158 (4)
O1	0.91927 (12)	0.40558 (8)	0.55651 (8)	0.0205 (3)
O2	0.64140 (11)	0.49652 (8)	0.46857 (7)	0.0168 (3)
O3	0.52602 (12)	0.42008 (8)	0.55820 (8)	0.0208 (3)
O4	0.69830 (13)	0.23372 (9)	0.49334 (8)	0.0254 (3)
O5	0.35180 (13)	0.77361 (9)	0.52790 (9)	0.0271 (3)
O6	0.52624 (12)	0.57807 (8)	0.56558 (7)	0.0178 (3)
O7	0.41030 (12)	0.51310 (9)	0.47014 (7)	0.0196 (3)
O8	0.12706 (12)	0.59799 (8)	0.55527 (7)	0.0182 (3)
N1	0.86478 (16)	0.54425 (10)	0.52973 (10)	0.0192 (3)
H1A	0.937 (2)	0.5624 (16)	0.5450 (13)	0.021 (6)*
H1B	0.813 (2)	0.5786 (16)	0.5057 (13)	0.023 (6)*
N4	0.48540 (15)	0.26379 (11)	0.49992 (10)	0.0196 (3)
H4A	0.465 (2)	0.2138 (17)	0.4823 (13)	0.021 (6)*
H4B	0.430 (2)	0.3011 (17)	0.5137 (14)	0.024 (6)*
N5	0.56219 (16)	0.73824 (12)	0.51558 (9)	0.0192 (3)
H5A	0.581 (2)	0.7872 (17)	0.4965 (14)	0.024 (6)*
H5B	0.615 (2)	0.6989 (17)	0.5181 (13)	0.022 (6)*
N8	0.18592 (17)	0.46122 (10)	0.52488 (10)	0.0194 (3)
H8A	0.116 (2)	0.4406 (16)	0.5394 (13)	0.020 (6)*
H8B	0.244 (2)	0.4282 (15)	0.5038 (12)	0.017 (5)*
C1	0.84351 (16)	0.45953 (11)	0.52973 (10)	0.0153 (4)
C2	0.72102 (17)	0.42811 (11)	0.49226 (10)	0.0148 (4)
H2	0.7452	0.3925	0.4480	0.018*
C3	0.63707 (17)	0.37138 (11)	0.54448 (10)	0.0156 (3)
H3	0.6839	0.3625	0.5924	0.019*
C4	0.60855 (17)	0.28272 (11)	0.50987 (10)	0.0155 (4)
C5	0.44083 (17)	0.72094 (11)	0.53269 (10)	0.0162 (4)
C6	0.41403 (17)	0.62771 (11)	0.55755 (10)	0.0147 (3)
H6	0.3662	0.6285	0.6057	0.018*
C7	0.33236 (16)	0.57937 (11)	0.49764 (10)	0.0148 (4)
H7	0.3131	0.6208	0.4563	0.018*
C8	0.20584 (16)	0.54575 (11)	0.52902 (10)	0.0143 (4)
O1S	0.72126 (14)	0.49644 (11)	0.32050 (8)	0.0300 (3)
H1S	0.686 (3)	0.508 (2)	0.368 (2)	0.064 (10)*
C1S	0.8477 (2)	0.53155 (18)	0.32258 (14)	0.0393 (6)
H1SA	0.9016	0.4969	0.3568	0.047*
H1SB	0.8448	0.5921	0.3412	0.047*
C2S	0.9054 (2)	0.53015 (15)	0.24611 (14)	0.0353 (5)
H2SA	0.9935	0.5523	0.2483	0.053*
H2SB	0.8542	0.5669	0.2129	0.053*
H2SC	0.9060	0.4704	0.2273	0.053*
N21	0.65708 (14)	0.21138 (10)	0.27680 (8)	0.0171 (3)
N36	0.46831 (14)	0.32994 (10)	0.28603 (8)	0.0158 (3)
H36	0.549 (2)	0.3079 (16)	0.3042 (13)	0.027 (6)*
C22	0.77691 (18)	0.17783 (13)	0.30942 (11)	0.0224 (4)
H22A	0.8018	0.1237	0.2834	0.027*
H22B	0.7619	0.1634	0.3623	0.027*
C23	0.88601 (18)	0.24296 (14)	0.30393 (11)	0.0246 (4)
H23A	0.9657	0.2167	0.3238	0.030*
H23B	0.8655	0.2948	0.3343	0.030*
C24	0.90722 (18)	0.27017 (14)	0.22337 (11)	0.0239 (4)
H24A	0.9745	0.3155	0.2207	0.029*
H24B	0.9359	0.2196	0.1937	0.029*
C25	0.78151 (18)	0.30531 (13)	0.19242 (11)	0.0209 (4)
H25A	0.7935	0.3217	0.1397	0.025*
H25B	0.7564	0.3581	0.2203	0.025*
C26	0.67503 (17)	0.23767 (12)	0.19834 (10)	0.0174 (4)
H26	0.7019	0.1852	0.1695	0.021*
C27	0.54688 (17)	0.27044 (12)	0.16604 (10)	0.0184 (4)
H27	0.5609	0.2857	0.1127	0.022*
C28	0.44581 (18)	0.19825 (12)	0.16977 (11)	0.0207 (4)
H28A	0.3638	0.2185	0.1480	0.025*
H28B	0.4752	0.1465	0.1419	0.025*
C29	0.42783 (18)	0.17587 (13)	0.25191 (11)	0.0198 (4)
H29	0.3643	0.1273	0.2558	0.024*
C30	0.55652 (18)	0.14444 (12)	0.28307 (11)	0.0202 (4)
H30A	0.5455	0.1285	0.3360	0.024*
H30B	0.5839	0.0917	0.2558	0.024*
C31	0.37693 (17)	0.25373 (11)	0.29610 (10)	0.0171 (4)
H31	0.3783	0.2373	0.3498	0.020*
C32	0.23995 (17)	0.28098 (12)	0.27705 (11)	0.0196 (4)
H32A	0.1810	0.2316	0.2863	0.023*
H32B	0.2350	0.2960	0.2237	0.023*
C33	0.19734 (18)	0.35914 (13)	0.32333 (11)	0.0227 (4)
H33A	0.1098	0.3769	0.3083	0.027*
H33B	0.1951	0.3429	0.3765	0.027*
C34	0.29007 (18)	0.43469 (12)	0.31202 (11)	0.0210 (4)
H34A	0.2858	0.4545	0.2598	0.025*
H34B	0.2645	0.4839	0.3443	0.025*
C35	0.42718 (17)	0.40773 (12)	0.33042 (11)	0.0198 (4)
H35A	0.4859	0.4568	0.3200	0.024*
H35B	0.4333	0.3940	0.3840	0.024*
C37	0.49511 (18)	0.35101 (12)	0.20593 (10)	0.0176 (4)
H37A	0.5589	0.3986	0.2029	0.021*
H37B	0.4152	0.3708	0.1815	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0133 (9)	0.0145 (9)	0.0196 (10)	−0.0011 (8)	0.0013 (7)	−0.0019 (8)
O1	0.0165 (6)	0.0148 (6)	0.0301 (7)	0.0004 (5)	−0.0036 (5)	0.0030 (5)
O2	0.0125 (6)	0.0160 (6)	0.0218 (6)	0.0015 (5)	0.0000 (5)	0.0045 (5)
O3	0.0193 (6)	0.0129 (6)	0.0300 (7)	0.0017 (5)	0.0114 (6)	−0.0011 (5)
O4	0.0184 (7)	0.0154 (6)	0.0425 (8)	0.0015 (5)	0.0065 (6)	−0.0028 (6)
O5	0.0189 (6)	0.0143 (6)	0.0482 (9)	0.0024 (5)	−0.0005 (6)	0.0019 (6)
O6	0.0177 (6)	0.0131 (6)	0.0227 (7)	0.0026 (5)	−0.0079 (5)	−0.0025 (5)
O7	0.0124 (6)	0.0247 (7)	0.0218 (6)	0.0020 (5)	−0.0006 (5)	−0.0107 (6)
O8	0.0144 (6)	0.0145 (6)	0.0257 (7)	0.0015 (5)	0.0023 (5)	−0.0039 (5)
N1	0.0133 (7)	0.0131 (8)	0.0313 (9)	0.0003 (6)	−0.0040 (7)	0.0004 (6)
N4	0.0156 (7)	0.0153 (8)	0.0279 (8)	−0.0012 (7)	−0.0003 (6)	−0.0021 (7)
N5	0.0168 (7)	0.0157 (8)	0.0251 (9)	−0.0008 (7)	−0.0021 (6)	0.0041 (7)
N8	0.0158 (8)	0.0140 (8)	0.0285 (9)	−0.0002 (7)	0.0037 (7)	0.0001 (7)
C1	0.0126 (8)	0.0140 (8)	0.0193 (9)	0.0010 (6)	0.0031 (7)	−0.0006 (7)
C2	0.0138 (8)	0.0125 (8)	0.0182 (9)	0.0002 (7)	0.0001 (7)	0.0005 (7)
C3	0.0144 (8)	0.0145 (8)	0.0181 (9)	−0.0004 (6)	0.0011 (7)	−0.0002 (7)
C4	0.0171 (8)	0.0114 (8)	0.0180 (8)	0.0006 (7)	0.0019 (7)	0.0029 (7)
C5	0.0155 (8)	0.0143 (8)	0.0188 (8)	−0.0001 (7)	−0.0027 (7)	−0.0021 (7)
C6	0.0142 (8)	0.0136 (8)	0.0163 (8)	0.0007 (6)	−0.0003 (7)	−0.0013 (7)
C7	0.0135 (8)	0.0148 (8)	0.0163 (8)	0.0005 (6)	−0.0006 (7)	−0.0014 (7)
C8	0.0143 (8)	0.0151 (9)	0.0134 (8)	0.0004 (6)	−0.0030 (7)	0.0004 (7)
O1S	0.0259 (7)	0.0368 (8)	0.0272 (8)	−0.0013 (7)	0.0017 (6)	0.0035 (7)
C1S	0.0338 (12)	0.0482 (14)	0.0358 (13)	−0.0110 (10)	0.0044 (10)	−0.0015 (11)
C2S	0.0371 (12)	0.0259 (10)	0.0430 (14)	−0.0044 (10)	0.0146 (10)	0.0016 (10)
N21	0.0161 (7)	0.0184 (8)	0.0169 (8)	0.0008 (6)	0.0005 (6)	0.0015 (6)
N36	0.0153 (7)	0.0159 (7)	0.0162 (7)	−0.0008 (6)	−0.0005 (6)	−0.0014 (6)
C22	0.0188 (9)	0.0260 (10)	0.0223 (10)	0.0050 (8)	0.0004 (8)	0.0042 (8)
C23	0.0163 (9)	0.0342 (11)	0.0233 (10)	0.0020 (8)	−0.0017 (7)	0.0002 (8)
C24	0.0171 (9)	0.0305 (10)	0.0241 (10)	−0.0006 (8)	0.0025 (7)	−0.0002 (8)
C25	0.0186 (9)	0.0250 (10)	0.0192 (9)	−0.0016 (7)	0.0040 (7)	0.0034 (8)
C26	0.0184 (8)	0.0184 (8)	0.0155 (9)	0.0004 (7)	0.0021 (7)	−0.0019 (7)
C27	0.0194 (9)	0.0210 (9)	0.0147 (8)	−0.0002 (7)	−0.0009 (7)	−0.0007 (7)
C28	0.0195 (9)	0.0206 (9)	0.0219 (9)	−0.0016 (7)	−0.0009 (7)	−0.0056 (7)
C29	0.0186 (9)	0.0160 (8)	0.0247 (10)	−0.0030 (7)	0.0016 (8)	−0.0008 (7)
C30	0.0203 (9)	0.0156 (8)	0.0247 (9)	0.0011 (7)	0.0027 (8)	0.0018 (7)
C31	0.0160 (8)	0.0170 (9)	0.0182 (9)	−0.0027 (7)	0.0012 (7)	0.0005 (7)
C32	0.0144 (8)	0.0212 (9)	0.0231 (9)	−0.0025 (7)	0.0004 (7)	−0.0003 (8)
C33	0.0164 (9)	0.0253 (10)	0.0263 (10)	0.0015 (8)	0.0014 (8)	−0.0012 (8)
C34	0.0206 (9)	0.0186 (9)	0.0239 (10)	0.0019 (7)	0.0000 (8)	−0.0034 (8)
C35	0.0206 (9)	0.0182 (8)	0.0206 (9)	−0.0001 (7)	−0.0007 (7)	−0.0058 (7)
C37	0.0178 (8)	0.0187 (9)	0.0164 (8)	−0.0010 (7)	0.0009 (7)	0.0030 (7)

Geometric parameters (Å, º)

B1—O2	1.486 (2)	N36—H36	0.96 (3)
B1—O3	1.469 (2)	N36—C31	1.521 (2)
B1—O6	1.468 (2)	N36—C35	1.501 (2)
B1—O7	1.467 (2)	N36—C37	1.504 (2)
O1—C1	1.243 (2)	C22—H22A	0.9900
O2—C2	1.406 (2)	C22—H22B	0.9900
O3—C3	1.400 (2)	C22—C23	1.518 (3)
O4—C4	1.237 (2)	C23—H23A	0.9900
O5—C5	1.234 (2)	C23—H23B	0.9900
O6—C6	1.404 (2)	C23—C24	1.526 (3)
O7—C7	1.394 (2)	C24—H24A	0.9900
O8—C8	1.242 (2)	C24—H24B	0.9900
N1—H1A	0.85 (3)	C24—C25	1.522 (3)
N1—H1B	0.87 (3)	C25—H25A	0.9900
N1—C1	1.322 (2)	C25—H25B	0.9900
N4—H4A	0.86 (3)	C25—C26	1.524 (2)
N4—H4B	0.85 (3)	C26—H26	1.0000
N4—C4	1.328 (2)	C26—C27	1.541 (2)
N5—H5A	0.85 (3)	C27—H27	1.0000
N5—H5B	0.82 (3)	C27—C28	1.532 (3)
N5—C5	1.328 (2)	C27—C37	1.530 (3)
N8—H8A	0.84 (3)	C28—H28A	0.9900
N8—H8B	0.87 (2)	C28—H28B	0.9900
N8—C8	1.319 (2)	C28—C29	1.530 (3)
C1—C2	1.522 (2)	C29—H29	1.0000
C2—H2	1.0000	C29—C30	1.532 (3)
C2—C3	1.552 (2)	C29—C31	1.532 (3)
C3—H3	1.0000	C30—H30A	0.9900
C3—C4	1.528 (2)	C30—H30B	0.9900
C5—C6	1.528 (2)	C31—H31	1.0000
C6—H6	1.0000	C31—C32	1.526 (2)
C6—C7	1.562 (2)	C32—H32A	0.9900
C7—H7	1.0000	C32—H32B	0.9900
C7—C8	1.524 (2)	C32—C33	1.529 (3)
O1S—H1S	0.95 (4)	C33—H33A	0.9900
O1S—C1S	1.424 (3)	C33—H33B	0.9900
C1S—H1SA	0.9900	C33—C34	1.525 (3)
C1S—H1SB	0.9900	C34—H34A	0.9900
C1S—C2S	1.502 (3)	C34—H34B	0.9900
C2S—H2SA	0.9800	C34—C35	1.524 (3)
C2S—H2SB	0.9800	C35—H35A	0.9900
C2S—H2SC	0.9800	C35—H35B	0.9900
N21—C22	1.473 (2)	C37—H37A	0.9900
N21—C26	1.481 (2)	C37—H37B	0.9900
N21—C30	1.473 (2)
O3—B1—O2	104.10 (14)	C23—C22—H22B	109.2
O6—B1—O2	112.88 (15)	C22—C23—H23A	109.5
O6—B1—O3	111.89 (15)	C22—C23—H23B	109.5
O7—B1—O2	110.10 (15)	C22—C23—C24	110.56 (16)
O7—B1—O3	113.28 (15)	H23A—C23—H23B	108.1
O7—B1—O6	104.81 (14)	C24—C23—H23A	109.5
C2—O2—B1	110.33 (14)	C24—C23—H23B	109.5
C3—O3—B1	111.89 (13)	C23—C24—H24A	109.9
C6—O6—B1	111.42 (13)	C23—C24—H24B	109.9
C7—O7—B1	111.04 (13)	H24A—C24—H24B	108.3
H1A—N1—H1B	121 (2)	C25—C24—C23	108.72 (16)
C1—N1—H1A	118.1 (16)	C25—C24—H24A	109.9
C1—N1—H1B	119.5 (16)	C25—C24—H24B	109.9
H4A—N4—H4B	123 (2)	C24—C25—H25A	109.4
C4—N4—H4A	119.2 (15)	C24—C25—H25B	109.4
C4—N4—H4B	118.2 (16)	C24—C25—C26	110.97 (16)
H5A—N5—H5B	121 (2)	H25A—C25—H25B	108.0
C5—N5—H5A	119.4 (16)	C26—C25—H25A	109.4
C5—N5—H5B	118.8 (17)	C26—C25—H25B	109.4
H8A—N8—H8B	121 (2)	N21—C26—C25	110.17 (15)
C8—N8—H8A	119.6 (16)	N21—C26—H26	108.1
C8—N8—H8B	119.3 (14)	N21—C26—C27	109.87 (14)
O1—C1—N1	123.50 (17)	C25—C26—H26	108.1
O1—C1—C2	119.50 (15)	C25—C26—C27	112.38 (15)
N1—C1—C2	116.97 (16)	C27—C26—H26	108.1
O2—C2—C1	113.04 (14)	C26—C27—H27	108.2
O2—C2—H2	108.5	C28—C27—C26	109.99 (15)
O2—C2—C3	105.78 (13)	C28—C27—H27	108.2
C1—C2—H2	108.5	C37—C27—C26	113.14 (15)
C1—C2—C3	112.47 (15)	C37—C27—H27	108.2
C3—C2—H2	108.5	C37—C27—C28	108.92 (15)
O3—C3—C2	105.76 (13)	C27—C28—H28A	110.4
O3—C3—H3	108.9	C27—C28—H28B	110.4
O3—C3—C4	112.87 (14)	H28A—C28—H28B	108.6
C2—C3—H3	108.9	C29—C28—C27	106.84 (15)
C4—C3—C2	111.35 (14)	C29—C28—H28A	110.4
C4—C3—H3	108.9	C29—C28—H28B	110.4
O4—C4—N4	124.33 (17)	C28—C29—H29	108.5
O4—C4—C3	119.65 (16)	C28—C29—C30	108.54 (15)
N4—C4—C3	116.01 (16)	C28—C29—C31	111.62 (16)
O5—C5—N5	124.57 (17)	C30—C29—H29	108.5
O5—C5—C6	119.94 (16)	C30—C29—C31	111.05 (15)
N5—C5—C6	115.46 (16)	C31—C29—H29	108.5
O6—C6—C5	112.87 (14)	N21—C30—C29	111.95 (15)
O6—C6—H6	109.5	N21—C30—H30A	109.2
O6—C6—C7	105.40 (13)	N21—C30—H30B	109.2
C5—C6—H6	109.5	C29—C30—H30A	109.2
C5—C6—C7	110.11 (14)	C29—C30—H30B	109.2
C7—C6—H6	109.5	H30A—C30—H30B	107.9
O7—C7—C6	106.03 (13)	N36—C31—C29	108.90 (14)
O7—C7—H7	108.6	N36—C31—H31	107.5
O7—C7—C8	112.78 (14)	N36—C31—C32	110.28 (14)
C6—C7—H7	108.6	C29—C31—H31	107.5
C8—C7—C6	112.11 (14)	C32—C31—C29	114.92 (15)
C8—C7—H7	108.6	C32—C31—H31	107.5
O8—C8—N8	123.74 (17)	C31—C32—H32A	109.3
O8—C8—C7	119.53 (15)	C31—C32—H32B	109.3
N8—C8—C7	116.71 (16)	C31—C32—C33	111.40 (15)
C1S—O1S—H1S	105 (2)	H32A—C32—H32B	108.0
O1S—C1S—H1SA	109.7	C33—C32—H32A	109.3
O1S—C1S—H1SB	109.7	C33—C32—H32B	109.3
O1S—C1S—C2S	109.9 (2)	C32—C33—H33A	109.7
H1SA—C1S—H1SB	108.2	C32—C33—H33B	109.7
C2S—C1S—H1SA	109.7	H33A—C33—H33B	108.2
C2S—C1S—H1SB	109.7	C34—C33—C32	110.03 (15)
C1S—C2S—H2SA	109.5	C34—C33—H33A	109.7
C1S—C2S—H2SB	109.5	C34—C33—H33B	109.7
C1S—C2S—H2SC	109.5	C33—C34—H34A	109.5
H2SA—C2S—H2SB	109.5	C33—C34—H34B	109.5
H2SA—C2S—H2SC	109.5	H34A—C34—H34B	108.0
H2SB—C2S—H2SC	109.5	C35—C34—C33	110.94 (16)
C22—N21—C26	111.66 (14)	C35—C34—H34A	109.5
C22—N21—C30	109.10 (14)	C35—C34—H34B	109.5
C30—N21—C26	110.72 (14)	N36—C35—C34	111.63 (15)
C31—N36—H36	103.5 (14)	N36—C35—H35A	109.3
C35—N36—H36	110.4 (15)	N36—C35—H35B	109.3
C35—N36—C31	111.85 (14)	C34—C35—H35A	109.3
C35—N36—C37	113.05 (14)	C34—C35—H35B	109.3
C37—N36—H36	103.9 (15)	H35A—C35—H35B	108.0
C37—N36—C31	113.36 (14)	N36—C37—C27	109.93 (14)
N21—C22—H22A	109.2	N36—C37—H37A	109.7
N21—C22—H22B	109.2	N36—C37—H37B	109.7
N21—C22—C23	112.17 (16)	C27—C37—H37A	109.7
H22A—C22—H22B	107.9	C27—C37—H37B	109.7
C23—C22—H22A	109.2	H37A—C37—H37B	108.2
B1—O2—C2—C1	−108.39 (16)	C6—C7—C8—N8	−120.88 (18)
B1—O2—C2—C3	15.10 (18)	N21—C22—C23—C24	−56.0 (2)
B1—O3—C3—C2	3.32 (19)	N21—C26—C27—C28	−59.94 (19)
B1—O3—C3—C4	−118.65 (16)	N21—C26—C27—C37	62.11 (19)
B1—O6—C6—C5	−120.07 (16)	N36—C31—C32—C33	−56.2 (2)
B1—O6—C6—C7	0.14 (19)	C22—N21—C26—C25	−56.9 (2)
B1—O7—C7—C6	11.42 (18)	C22—N21—C26—C27	178.80 (16)
B1—O7—C7—C8	−111.63 (16)	C22—N21—C30—C29	178.55 (15)
O1—C1—C2—O2	176.49 (15)	C22—C23—C24—C25	55.8 (2)
O1—C1—C2—C3	56.8 (2)	C23—C24—C25—C26	−57.6 (2)
O2—B1—O3—C3	5.43 (19)	C24—C25—C26—N21	58.3 (2)
O2—B1—O6—C6	126.27 (16)	C24—C25—C26—C27	−178.85 (15)
O2—B1—O7—C7	−132.99 (15)	C25—C26—C27—C28	177.01 (15)
O2—C2—C3—O3	−11.32 (18)	C25—C26—C27—C37	−60.9 (2)
O2—C2—C3—C4	111.63 (15)	C26—N21—C22—C23	56.4 (2)
O3—B1—O2—C2	−13.09 (19)	C26—N21—C30—C29	−58.2 (2)
O3—B1—O6—C6	−116.70 (16)	C26—C27—C28—C29	61.34 (19)
O3—B1—O7—C7	110.92 (16)	C26—C27—C37—N36	−62.03 (19)
O3—C3—C4—O4	178.42 (16)	C27—C28—C29—C30	−60.35 (19)
O3—C3—C4—N4	−1.8 (2)	C27—C28—C29—C31	62.37 (19)
O5—C5—C6—O6	−175.42 (16)	C28—C27—C37—N36	60.62 (19)
O5—C5—C6—C7	67.1 (2)	C28—C29—C30—N21	60.2 (2)
O6—B1—O2—C2	108.45 (17)	C28—C29—C31—N36	−56.56 (19)
O6—B1—O3—C3	−116.78 (16)	C28—C29—C31—C32	67.7 (2)
O6—B1—O7—C7	−11.32 (19)	C29—C31—C32—C33	−179.73 (15)
O6—C6—C7—O7	−7.06 (18)	C30—N21—C22—C23	179.13 (16)
O6—C6—C7—C8	116.41 (15)	C30—N21—C26—C25	−178.63 (15)
O7—B1—O2—C2	−134.81 (15)	C30—N21—C26—C27	57.03 (19)
O7—B1—O3—C3	125.01 (16)	C30—C29—C31—N36	64.71 (19)
O7—B1—O6—C6	6.45 (19)	C30—C29—C31—C32	−171.03 (15)
O7—C7—C8—O8	−179.87 (15)	C31—N36—C35—C34	−55.5 (2)
O7—C7—C8—N8	−1.3 (2)	C31—N36—C37—C27	−55.99 (19)
N1—C1—C2—O2	−5.5 (2)	C31—C29—C30—N21	−62.9 (2)
N1—C1—C2—C3	−125.23 (18)	C31—C32—C33—C34	56.9 (2)
N5—C5—C6—O6	6.3 (2)	C32—C33—C34—C35	−56.0 (2)
N5—C5—C6—C7	−111.14 (17)	C33—C34—C35—N36	55.9 (2)
C1—C2—C3—O3	112.52 (16)	C35—N36—C31—C29	−177.69 (14)
C1—C2—C3—C4	−124.53 (16)	C35—N36—C31—C32	55.34 (19)
C2—C3—C4—O4	59.6 (2)	C35—N36—C37—C27	175.37 (14)
C2—C3—C4—N4	−120.61 (18)	C37—N36—C31—C29	53.05 (19)
C5—C6—C7—O7	114.95 (15)	C37—N36—C31—C32	−73.91 (18)
C5—C6—C7—C8	−121.57 (15)	C37—N36—C35—C34	73.88 (19)
C6—C7—C8—O8	60.5 (2)	C37—C27—C28—C29	−63.18 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O8^i	0.85 (3)	2.06 (3)	2.891 (2)	166 (2)
N1—H1B···O2	0.87 (3)	2.28 (2)	2.677 (2)	107.3 (18)
N4—H4A···O1^ii	0.86 (3)	2.02 (3)	2.880 (2)	178 (2)
N4—H4B···O3	0.85 (3)	2.24 (2)	2.657 (2)	110.3 (19)
N5—H5B···O6	0.82 (3)	2.25 (2)	2.650 (2)	111 (2)
N8—H8A···O1^iii	0.84 (3)	2.14 (3)	2.962 (2)	167 (2)
N8—H8B···O7	0.87 (2)	2.25 (2)	2.659 (2)	108.1 (17)
O1S—H1S···O2	0.95 (4)	1.87 (4)	2.793 (2)	162 (3)
N36—H36···N21	0.96 (3)	1.93 (3)	2.687 (2)	134 (2)

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, −z+1; (iii) x−1, y, z.