4-Methyl­pyridinium bis­(pyrocatecholato-κ2O,O′)­borate catechol solvate

Baber, R.A.; Charmant, J.P.H.; Moore, J.D.; Norman, N.C.; Orpen, A.G.

doi:10.1107/S1600536804013108

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 60| Part 7| July 2004| Pages o1140-o1142

https://doi.org/10.1107/S1600536804013108

4-Methylpyridinium bis(pyrocatecholato-κ²O,O′)borate catechol solvate

R. Angharad Baber,^a Jonathan P. H. Charmant,^a ^* Jonathan D. Moore,^a Nicholas C. Norman ^a and A. Guy Orpen ^a

^aSchool of Chemistry, University of Bristol, Bristol BS8 1TS, England
^*Correspondence e-mail: jon.charmant@bris.ac.uk

(Received 20 May 2004; accepted 1 June 2004; online 12 June 2004)

Unlike the previously reported salts of the 4-methylpyridinium cation and the bis(pyrocatecholato)borate anion [Clegg et al. (1998 ). Acta Cryst. C54, 1875–1880], the title compound, C₆H₈N⁺·C₁₂H₈BO₄⁻·C₆H₆O₂, is a solvate containing a molecule of catechol. The crystal packing is influenced by N—H⋯O and O—H⋯O hydrogen bonds.

Comment

In addition to the ammonium cations [NH₄]⁺ (Goddard et al., 1993 ) and [NH₂Me₂]⁺ (Clegg, Elsegood et al., 1998 ), the bis(pyrocatecholato)borate anion [B(1,2-O₂C₆H₄)₂]⁻ has been found to crystallize with a number of pyridinium cations. These include [2-MeC₅H₄NH]⁺ and two polymorphs containing [4-MeC₅H₄NH]⁺ (Clegg, Scott et al., 1998). [NHEt₃]⁺ (Mohr et al., 1990 ) and the unsubstituted pyridinium cation [C₅H₅NH]⁺ (Griffin et al., 1996 ) also form salts with [B(1,2-O₂C₆H₄)₂]⁻, although in these cases a molecule of catechol is incorporated into the structure. The structures of [1,10-phenH][B(1,2-O₂C₆H₄)₂] (phen = phenanthroline), and its dichloromethane solvate (Clegg, Scott et al., 1998) have also been determined as has the structure of the phosphonium salt [PHMe₃][B(1,2-O₂C₆H₄)₂] (Clegg, Scott et al., 1998) and a range of salts containing cationic rhodium or iridium phosphine complexes (Clegg et al., 1999 ). In this paper, we report the structure of a [4-MeC₅H₄NH]⁺ salt of [(C₆H₄O₂)₂B]⁻ that, unlike the crystal structures previously reported for salts of [4-MeC₅H₄NH]⁺ and [(C₆H₄O₂)₂B]⁻ (Clegg, Scott et al., 1998), but in common with the pyridinium and triethylammonium salts, includes a molecule of catechol in the structure.

The molecular structure of (I) is shown in Fig. 1. The crystal structure contains hydrogen bonds between the catechol molecules and the catecholate ligands of the [B(1,2-O₂C₆H₄)₂]⁻ anions. The 4-methylpyridinium cations also form hydrogen bonds to the catechol molecules, producing a ribbon structure (see Fig. 2). These ribbons crosslink through hydrogen bonds between the catecholate ligands and pyridinium cations to form a one-dimensional hydrogen-bonded polymer (see Fig. 3).

Figure 1
The molecular structure of (I

), showing displacement ellipsoids drawn at the 50% probability level. The solvent catechol molecule has been transformed by the symmetry operation (x, y, z − 1).

Figure 2
Stick representation (colour code: C grey, H white, O red, B pink, N blue) of the hydrogen-bonded (dashed lines) ribbon polymers formed in (I

Figure 3
Cross-linking hydrogen bonds (dashed lines) between ribbons in (I

). The colour code is as in Fig. 2

Experimental

B₂(cat)₃ (0.1 g, 0.029 mmol) was dissolved in CH₂Cl₂ (4 ml) in a small Schlenk tube to which 4-picoline (0.04 g, 0.058 mmol) was added and the mixture stirred for 1 h at room temperature. After this time, hexane (4 ml) was added as an overlayer and solvent diffusion over a period of days at 243 K afforded colourless crystals of [4-MeC₅H₄NH][B(1,2-O₂C₆H₄)₂]. C₁₈H₁₆BNO₄ requires: N 4.35, C 67.30, H 5.00%; found: N 4.40, C 67.65, H 5.75%. ¹¹B {¹H} NMR: δ 13.2 (s). Although the microanalytical data are consistent with the formula [4–MeC₅H₄NH][B(1,2-O₂C₆H₄)₂], confirmed by X-ray crystallography, one (colourless) crystal examined was found to have the composition [4-MeC₅H₄NH][B(1,2-O₂C₆H₄)₂]·1,2-(HO)₂C₆H₄. There are no obvious morphology differences between the two phases.

Crystal data

C₆H₈N⁺·C₁₂H₈BO₄⁻·C₆H₆O₂
M_r = 431.24
Monoclinic, P2₁/n
a = 10.0007 (14) Å
b = 12.9573 (17) Å
c = 16.396 (3) Å
β = 96.872 (11)°
V = 2109.3 (6) Å³
Z = 4
D_x = 1.355 Mg m⁻³
D_m = 1.340 Mg m⁻³
Mo Kα radiation
Cell parameters from 4189 reflections
θ = 2.5–25.8°
μ = 0.10 mm⁻¹
T = 100 (3) K
Block, colourless
0.05 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.929, T_max = 0.990
23718 measured reflections
4828 independent reflections
3973 reflections with I > 2σ(I)'
R_int = 0.037
θ_max = 27.5°
h = −12 → 12
k = −16 → 16
l = −21 → 21

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.110
S = 1.03
4828 reflections
299 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0504P)² + 0.7965P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

C1—O1	1.3662 (17)
C6—O2	1.3681 (17)
C7—O3	1.3659 (17)
C12—O4	1.3756 (16)
B1—O2	1.4742 (19)
B1—O1	1.4746 (19)
B1—O4	1.4820 (19)
C19—O5	1.3731 (17)
C24—O6	1.3664 (18)

O2—B1—O1	105.58 (11)
O2—B1—O4	112.77 (12)
O1—B1—O4	113.49 (12)
O2—B1—O3	111.09 (12)
O1—B1—O3	110.74 (12)
O4—B1—O3	103.32 (11)
C1—O1—B1	105.89 (11)
C6—O2—B1	105.98 (11)
C7—O3—B1	108.12 (11)
C12—O4—B1	108.15 (11)

Table 2
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.872 (15)	2.425 (18)	2.8864 (17)	113.6 (14)
N1—H1⋯O5ⁱ	0.872 (15)	2.096 (17)	2.8621 (18)	146.3 (16)
N1—H1⋯O6ⁱ	0.872 (15)	2.587 (17)	3.1073 (18)	119.2 (14)
O5—H5⋯O3ⁱⁱ	0.864 (15)	1.788 (16)	2.6469 (15)	172.5 (17)
O6—H6⋯O4ⁱⁱⁱ	0.871 (15)	1.793 (16)	2.6600 (15)	173.5 (18)
Symmetry codes: (i) x,y,z-1; (ii) 2-x,1-y,1-z; (iii) 1-x,1-y,1-z.

The NH H atom of the pyridinium cation and all hydroxy H atoms were located in difference maps. Distance restraints of 0.88 (3) and 0.84 (3) Å were applied to the N—H and O—H bond lengths, respectively. Methyl H atoms were located using a rotating group refinement, with C—H bond lengths constrained to 0.96 Å. All other H atoms were positioned in ideal geometries and refined by riding on their carrier atom. All H atoms were assigned displacement parameters equal to 1.5 times (methyl and hydroxyl H atoms) or 1.2 times (all other H atoms) U_eq of their parent atom.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT and SHELXTL (Bruker, 2002); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536804013108/hb6050sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536804013108/hb6050Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SHELXTL (Bruker, 2002); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top

Crystal data top

C₆H₈N⁺·C₁₂H₈BO₄⁻·C₆H₆O₂	F(000) = 904
M_r = 431.24	D_x = 1.355 Mg m⁻³ D_m = 1.340 Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4189 reflections
a = 10.0007 (14) Å	θ = 2.5–25.8°
b = 12.9573 (17) Å	µ = 0.10 mm⁻¹
c = 16.396 (3) Å	T = 100 K
β = 96.872 (11)°	Block, colourless
V = 2109.3 (6) Å³	0.05 × 0.05 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4828 independent reflections
Radiation source: fine-focus sealed tube	3973 reflections with I > 2σ(I)'
Graphite monochromator	R_int = 0.037
Detector resolution: 8.192 pixels mm^-1	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −16→16
T_min = 0.929, T_max = 0.990	l = −21→21
23718 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0504P)² + 0.7965P] where P = (F_o² + 2F_c²)/3
4828 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.29 e Å⁻³
3 restraints	Δρ_min = −0.25 e Å⁻³

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.81009 (14)	0.73736 (12)	−0.08826 (8)	0.0205 (3)
C2	0.83417 (16)	0.79292 (13)	−0.15693 (9)	0.0260 (3)
H2	0.8475	0.8655	−0.1547	0.031*
C3	0.83815 (16)	0.73753 (14)	−0.23020 (9)	0.0301 (4)
H3	0.8541	0.7734	−0.2786	0.036*
C4	0.81930 (16)	0.63191 (14)	−0.23323 (9)	0.0303 (4)
H4	0.8221	0.5966	−0.2838	0.036*
C5	0.79609 (15)	0.57553 (13)	−0.16294 (9)	0.0262 (3)
H5A	0.7840	0.5028	−0.1648	0.031*
C6	0.79161 (14)	0.63043 (12)	−0.09140 (8)	0.0211 (3)
C7	0.90025 (14)	0.66835 (10)	0.17549 (8)	0.0172 (3)
C8	0.98987 (15)	0.66026 (11)	0.24587 (9)	0.0219 (3)
H8	1.0839	0.6533	0.2435	0.026*
C9	0.93661 (16)	0.66266 (11)	0.32102 (9)	0.0243 (3)
H9	0.9957	0.6573	0.3707	0.029*
C10	0.79955 (16)	0.67271 (11)	0.32448 (9)	0.0225 (3)
H10	0.7661	0.6734	0.3763	0.027*
C11	0.70917 (15)	0.68191 (10)	0.25224 (9)	0.0195 (3)
H11	0.6150	0.6890	0.2541	0.023*
C12	0.76268 (14)	0.68016 (10)	0.17872 (8)	0.0161 (3)
B1	0.79639 (16)	0.68115 (13)	0.04148 (10)	0.0187 (3)
O1	0.80197 (10)	0.77338 (8)	−0.01069 (6)	0.0211 (2)
O2	0.76987 (10)	0.59384 (8)	−0.01582 (6)	0.0222 (2)
O3	0.92679 (10)	0.66676 (8)	0.09570 (6)	0.0202 (2)
O4	0.69591 (10)	0.68919 (8)	0.10068 (6)	0.0191 (2)
C13	0.6421 (2)	0.43363 (13)	0.34169 (10)	0.0342 (4)
H13A	0.7205	0.4080	0.3776	0.051*
H13B	0.5640	0.3899	0.3479	0.051*
H13C	0.6229	0.5048	0.3569	0.051*
C14	0.67129 (16)	0.43076 (11)	0.25411 (9)	0.0224 (3)
C15	0.80203 (16)	0.42629 (11)	0.23393 (9)	0.0236 (3)
H15	0.8758	0.4244	0.2762	0.028*
C16	0.82501 (16)	0.42467 (11)	0.15307 (10)	0.0264 (3)
H16	0.9145	0.4217	0.1393	0.032*
C17	0.59375 (17)	0.43127 (12)	0.11020 (10)	0.0290 (4)
H17	0.5221	0.4329	0.0666	0.035*
C18	0.56675 (16)	0.43292 (12)	0.19011 (10)	0.0271 (3)
H18	0.4761	0.4356	0.2019	0.033*
N1	0.72116 (15)	0.42732 (10)	0.09378 (8)	0.0266 (3)
H1	0.7377 (18)	0.4251 (14)	0.0428 (9)	0.032*
C19	0.77804 (14)	0.24734 (11)	0.95478 (8)	0.0177 (3)
C20	0.85497 (15)	0.15817 (11)	0.96525 (8)	0.0205 (3)
H20	0.9505	0.1625	0.9723	0.025*
C21	0.79204 (16)	0.06230 (12)	0.96543 (9)	0.0234 (3)
H21	0.8446	0.0011	0.9717	0.028*
C22	0.65281 (16)	0.05611 (12)	0.95649 (9)	0.0253 (3)
H22	0.6101	−0.0093	0.9568	0.030*
C23	0.57540 (15)	0.14533 (12)	0.94700 (8)	0.0227 (3)
H23	0.4799	0.1407	0.9415	0.027*
C24	0.63701 (14)	0.24125 (11)	0.94544 (8)	0.0188 (3)
O5	0.83169 (10)	0.34485 (8)	0.95439 (7)	0.0216 (2)
H5	0.9133 (15)	0.3402 (14)	0.9425 (11)	0.032*
O6	0.56912 (10)	0.33270 (8)	0.93487 (6)	0.0233 (2)
H6	0.4834 (15)	0.3205 (14)	0.9229 (12)	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0141 (7)	0.0329 (8)	0.0142 (7)	−0.0007 (6)	0.0004 (5)	−0.0012 (6)
C2	0.0220 (8)	0.0370 (9)	0.0189 (7)	−0.0014 (6)	0.0017 (6)	0.0054 (6)
C3	0.0214 (8)	0.0539 (11)	0.0153 (7)	−0.0004 (7)	0.0029 (6)	0.0049 (7)
C4	0.0215 (8)	0.0537 (11)	0.0158 (7)	0.0021 (7)	0.0024 (6)	−0.0084 (7)
C5	0.0198 (7)	0.0377 (9)	0.0211 (7)	0.0011 (6)	0.0023 (6)	−0.0076 (6)
C6	0.0149 (7)	0.0328 (8)	0.0156 (7)	−0.0002 (6)	0.0017 (5)	0.0000 (6)
C7	0.0198 (7)	0.0165 (6)	0.0162 (7)	−0.0013 (5)	0.0050 (5)	−0.0002 (5)
C8	0.0191 (7)	0.0227 (7)	0.0232 (7)	0.0017 (6)	0.0000 (6)	0.0017 (6)
C9	0.0334 (9)	0.0212 (7)	0.0168 (7)	0.0002 (6)	−0.0033 (6)	0.0015 (6)
C10	0.0356 (9)	0.0172 (7)	0.0157 (7)	−0.0009 (6)	0.0073 (6)	0.0000 (5)
C11	0.0219 (7)	0.0170 (7)	0.0207 (7)	−0.0002 (5)	0.0078 (6)	−0.0006 (5)
C12	0.0177 (7)	0.0148 (6)	0.0156 (7)	−0.0009 (5)	0.0018 (5)	0.0006 (5)
B1	0.0151 (7)	0.0239 (8)	0.0175 (8)	−0.0006 (6)	0.0038 (6)	−0.0002 (6)
O1	0.0243 (5)	0.0252 (5)	0.0140 (5)	−0.0018 (4)	0.0034 (4)	−0.0003 (4)
O2	0.0267 (6)	0.0249 (5)	0.0159 (5)	−0.0026 (4)	0.0058 (4)	−0.0014 (4)
O3	0.0152 (5)	0.0311 (6)	0.0150 (5)	0.0006 (4)	0.0045 (4)	0.0008 (4)
O4	0.0146 (5)	0.0276 (5)	0.0152 (5)	0.0003 (4)	0.0029 (4)	0.0005 (4)
C13	0.0561 (12)	0.0256 (8)	0.0235 (8)	−0.0040 (8)	0.0153 (8)	−0.0021 (6)
C14	0.0337 (9)	0.0136 (6)	0.0211 (7)	−0.0020 (6)	0.0079 (6)	−0.0010 (5)
C15	0.0282 (8)	0.0158 (7)	0.0260 (8)	−0.0013 (6)	−0.0004 (6)	−0.0003 (6)
C16	0.0262 (8)	0.0189 (7)	0.0362 (9)	−0.0023 (6)	0.0117 (7)	−0.0017 (6)
C17	0.0335 (9)	0.0276 (8)	0.0245 (8)	0.0032 (7)	−0.0025 (7)	−0.0013 (6)
C18	0.0238 (8)	0.0271 (8)	0.0315 (8)	−0.0009 (6)	0.0074 (6)	−0.0036 (6)
N1	0.0420 (8)	0.0218 (6)	0.0180 (6)	−0.0013 (6)	0.0114 (6)	0.0006 (5)
C19	0.0185 (7)	0.0228 (7)	0.0125 (6)	−0.0034 (5)	0.0047 (5)	−0.0013 (5)
C20	0.0199 (7)	0.0270 (8)	0.0151 (7)	0.0008 (6)	0.0044 (5)	0.0000 (6)
C21	0.0323 (9)	0.0228 (7)	0.0158 (7)	0.0022 (6)	0.0051 (6)	0.0013 (6)
C22	0.0343 (9)	0.0253 (8)	0.0167 (7)	−0.0100 (6)	0.0049 (6)	−0.0012 (6)
C23	0.0203 (7)	0.0327 (8)	0.0152 (7)	−0.0083 (6)	0.0022 (5)	0.0009 (6)
C24	0.0188 (7)	0.0264 (7)	0.0115 (6)	−0.0014 (6)	0.0033 (5)	−0.0002 (5)
O5	0.0155 (5)	0.0223 (5)	0.0285 (6)	−0.0021 (4)	0.0085 (4)	−0.0027 (4)
O6	0.0140 (5)	0.0294 (6)	0.0262 (6)	0.0002 (4)	0.0014 (4)	−0.0008 (4)

Geometric parameters (Å, º) top

C1—O1	1.3662 (17)	C13—H13A	0.9800
C1—C2	1.382 (2)	C13—H13B	0.9800
C1—C6	1.398 (2)	C13—H13C	0.9800
C2—C3	1.404 (2)	C14—C15	1.388 (2)
C2—H2	0.9500	C14—C18	1.390 (2)
C3—C4	1.382 (3)	C15—C16	1.373 (2)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.407 (2)	C16—N1	1.335 (2)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.377 (2)	C17—N1	1.335 (2)
C5—H5A	0.9500	C17—C18	1.369 (2)
C6—O2	1.3681 (17)	C17—H17	0.9500
C7—O3	1.3659 (17)	C18—H18	0.9500
C7—C8	1.378 (2)	N1—H1	0.871 (14)
C7—C12	1.392 (2)	C19—O5	1.3731 (17)
C8—C9	1.400 (2)	C19—C20	1.387 (2)
C8—H8	0.9500	C19—C24	1.403 (2)
C9—C10	1.385 (2)	C20—C21	1.393 (2)
C9—H9	0.9500	C20—H20	0.9500
C10—C11	1.406 (2)	C21—C22	1.385 (2)
C10—H10	0.9500	C21—H21	0.9500
C11—C12	1.3764 (19)	C22—C23	1.390 (2)
C11—H11	0.9500	C22—H22	0.9500
C12—O4	1.3756 (16)	C23—C24	1.389 (2)
B1—O2	1.4742 (19)	C23—H23	0.9500
B1—O1	1.4746 (19)	C24—O6	1.3664 (18)
B1—O4	1.4820 (19)	O5—H5	0.864 (14)
B1—O3	1.4993 (18)	O6—H6	0.871 (15)
C13—C14	1.499 (2)

O1—C1—C2	128.04 (14)	C12—O4—B1	108.15 (11)
O1—C1—C6	110.52 (12)	C14—C13—H13A	109.5
C2—C1—C6	121.44 (14)	C14—C13—H13B	109.5
C1—C2—C3	117.16 (15)	H13A—C13—H13B	109.5
C1—C2—H2	121.4	C14—C13—H13C	109.5
C3—C2—H2	121.4	H13A—C13—H13C	109.5
C4—C3—C2	121.29 (15)	H13B—C13—H13C	109.5
C4—C3—H3	119.4	C15—C14—C18	117.76 (14)
C2—C3—H3	119.4	C15—C14—C13	121.74 (15)
C3—C4—C5	121.34 (14)	C18—C14—C13	120.50 (15)
C3—C4—H4	119.3	C16—C15—C14	120.16 (14)
C5—C4—H4	119.3	C16—C15—H15	119.9
C6—C5—C4	117.06 (16)	C14—C15—H15	119.9
C6—C5—H5A	121.5	N1—C16—C15	119.82 (15)
C4—C5—H5A	121.5	N1—C16—H16	120.1
O2—C6—C5	128.12 (15)	C15—C16—H16	120.1
O2—C6—C1	110.17 (12)	N1—C17—C18	119.74 (15)
C5—C6—C1	121.71 (14)	N1—C17—H17	120.1
O3—C7—C8	128.28 (13)	C18—C17—H17	120.1
O3—C7—C12	110.14 (12)	C17—C18—C14	120.36 (15)
C8—C7—C12	121.57 (13)	C17—C18—H18	119.8
C7—C8—C9	117.23 (14)	C14—C18—H18	119.8
C7—C8—H8	121.4	C17—N1—C16	122.16 (14)
C9—C8—H8	121.4	C17—N1—H1	119.4 (12)
C10—C9—C8	121.39 (13)	C16—N1—H1	118.4 (12)
C10—C9—H9	119.3	O5—C19—C20	123.76 (13)
C8—C9—H9	119.3	O5—C19—C24	116.08 (12)
C9—C10—C11	120.87 (13)	C20—C19—C24	120.14 (13)
C9—C10—H10	119.6	C19—C20—C21	119.93 (14)
C11—C10—H10	119.6	C19—C20—H20	120.0
C12—C11—C10	117.27 (14)	C21—C20—H20	120.0
C12—C11—H11	121.4	C22—C21—C20	120.02 (14)
C10—C11—H11	121.4	C22—C21—H21	120.0
O4—C12—C11	128.09 (13)	C20—C21—H21	120.0
O4—C12—C7	110.25 (12)	C21—C22—C23	120.21 (14)
C11—C12—C7	121.66 (13)	C21—C22—H22	119.9
O2—B1—O1	105.58 (11)	C23—C22—H22	119.9
O2—B1—O4	112.77 (12)	C24—C23—C22	120.27 (14)
O1—B1—O4	113.49 (12)	C24—C23—H23	119.9
O2—B1—O3	111.09 (12)	C22—C23—H23	119.9
O1—B1—O3	110.74 (12)	O6—C24—C23	124.31 (13)
O4—B1—O3	103.32 (11)	O6—C24—C19	116.29 (12)
C1—O1—B1	105.89 (11)	C23—C24—C19	119.40 (13)
C6—O2—B1	105.98 (11)	C19—O5—H5	108.5 (12)
C7—O3—B1	108.12 (11)	C24—O6—H6	109.4 (12)

O1—C1—C2—C3	179.81 (14)	O3—B1—O2—C6	−106.83 (13)
C6—C1—C2—C3	0.5 (2)	C8—C7—O3—B1	−178.44 (14)
C1—C2—C3—C4	−0.3 (2)	C12—C7—O3—B1	1.39 (15)
C2—C3—C4—C5	−0.3 (2)	O2—B1—O3—C7	−121.96 (12)
C3—C4—C5—C6	0.7 (2)	O1—B1—O3—C7	121.05 (12)
C4—C5—C6—O2	179.55 (14)	O4—B1—O3—C7	−0.79 (14)
C4—C5—C6—C1	−0.4 (2)	C11—C12—O4—B1	−179.18 (14)
O1—C1—C6—O2	0.45 (16)	C7—C12—O4—B1	0.93 (15)
C2—C1—C6—O2	179.84 (13)	O2—B1—O4—C12	119.94 (12)
O1—C1—C6—C5	−179.60 (13)	O1—B1—O4—C12	−120.06 (12)
C2—C1—C6—C5	−0.2 (2)	O3—B1—O4—C12	−0.09 (14)
O3—C7—C8—C9	−179.13 (13)	C18—C14—C15—C16	0.3 (2)
C12—C7—C8—C9	1.0 (2)	C13—C14—C15—C16	−179.44 (13)
C7—C8—C9—C10	0.0 (2)	C14—C15—C16—N1	0.0 (2)
C8—C9—C10—C11	−0.7 (2)	N1—C17—C18—C14	0.2 (2)
C9—C10—C11—C12	0.2 (2)	C15—C14—C18—C17	−0.4 (2)
C10—C11—C12—O4	−179.01 (13)	C13—C14—C18—C17	179.38 (14)
C10—C11—C12—C7	0.9 (2)	C18—C17—N1—C16	0.1 (2)
O3—C7—C12—O4	−1.49 (15)	C15—C16—N1—C17	−0.2 (2)
C8—C7—C12—O4	178.36 (12)	O5—C19—C20—C21	179.52 (13)
O3—C7—C12—C11	178.61 (12)	C24—C19—C20—C21	0.8 (2)
C8—C7—C12—C11	−1.5 (2)	C19—C20—C21—C22	−1.0 (2)
C2—C1—O1—B1	−171.26 (15)	C20—C21—C22—C23	0.2 (2)
C6—C1—O1—B1	8.08 (15)	C21—C22—C23—C24	0.8 (2)
O2—B1—O1—C1	−12.99 (14)	C22—C23—C24—O6	178.73 (13)
O4—B1—O1—C1	−137.00 (12)	C22—C23—C24—C19	−1.0 (2)
O3—B1—O1—C1	107.34 (12)	O5—C19—C24—O6	1.66 (18)
C5—C6—O2—B1	171.28 (14)	C20—C19—C24—O6	−179.55 (12)
C1—C6—O2—B1	−8.77 (15)	O5—C19—C24—C23	−178.63 (12)
O1—B1—O2—C6	13.27 (14)	C20—C19—C24—C23	0.2 (2)
O4—B1—O2—C6	137.73 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.87 (2)	2.43 (2)	2.8864 (17)	114 (1)
N1—H1···O5ⁱ	0.87 (2)	2.10 (2)	2.8621 (18)	146 (2)
N1—H1···O6ⁱ	0.87 (2)	2.59 (2)	3.1073 (18)	119 (1)
O5—H5···O3ⁱⁱ	0.86 (2)	1.79 (2)	2.6469 (15)	173 (2)
O6—H6···O4ⁱⁱⁱ	0.87 (2)	1.79 (2)	2.6600 (15)	174 (2)

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

References

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Volume 60| Part 7| July 2004| Pages o1140-o1142

https://doi.org/10.1107/S1600536804013108

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