organic compounds
2,6-Dihydroxy-4-oxo-2-(pyridin-1-ium-3-yl)-4H-1,3,2-benzodioxaborinin-2-ide 0.67-hydrate
aFacultad de Ingenieria Mochis, Universidad Autónoma de Sinaloa, Fuente Poseidón y Prol. A. Flores S/N, CP 81223, C.U. Los Mochis, Sinaloa, México, and bCentro de Graduados e Investigación en Química, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, CP 62210, Cuernavaca, Morelos, México
*Correspondence e-mail: cenriqueza@yahoo.com.mx
The 12H10BNO5·0.67H2O, contains three independent pyridinylboronic acid adopting zwitterionic forms and two water molecules. The six-membered heterocyclic rings in the boronic have half-chair conformations and the deviations of the B atoms from the boronate mean planes range from 0.456 (3) to 0.657 (3) Å. All of the B atoms have tetrahedral coordination environments, with B—O and B—C bond lengths of 1.446 (4)–1.539 (3) and 1.590 (5)–1.609 (5) Å, respectively. In the crystal, the ester and water molecules are linked into a three-dimensional network by a large number of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds. The crystal packing is further accomplished by π–π interactions, with centroid–centroid distances of 3.621 (4)–3.787 (4) Å.
of the title compound, CCCDC reference: 988588
Related literature
For the synthesis and applications of boronic ); Fujita et al. (2008); Severin (2009). For related structures, see: Barba et al. (2010).
see: Höpfl (2002Experimental
Crystal data
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Data collection: SMART (Bruker, 2000); cell SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 988588
10.1107/S1600536814004267/is5341sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814004267/is5341Isup2.hkl
C12H10BNO5 was formed from a solution of 3-pyridin boronic acid (0.05 g, 0.41 mmol), 2,5-dihydroxybenzoic acid (0.06 g, 0.41 mmol) in a solvent mixture of CH3OH (8 ml) and H2O (2 ml), which was heated under reflux for 1 h, giving a clear transparent solution. Cooling the reaction mixture slowly to room temperature afforded yellow crystals suitable for X-ray diffraction in approximately 55% yield. 11B NMR (64 MHz, DMSO-d6) δ: 3.8 p.p.m..
H atoms bonded to C atoms were positioned geometrically and constrained using the riding-model approximation [C—H = 0.95 A and Uiso(H) = 1.2Ueq(C)]. H atoms bonded to O and N were initially located in a difference Fourier map; then, the positions were refined with O(N)—H distance restraints of 0.840 (1) A and with Uiso(H) = 1.5Ueq(O,N).
Data collection: SMART (Bruker, 2000); cell
SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT (Bruker, 2001); program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-NT (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Molecular structures in the asymmetric unit of the title compound, with the atom-labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. A crystal packing diagram of the title compound viewed along the b axis, showing the three-dimensional hydrogen-bonded network. Hydrogen bonds were drawn as dashed lines. |
C12H10BNO5·0.67H2O | Z = 6 |
Mr = 271.03 | F(000) = 844 |
Triclinic, P1 | Dx = 1.500 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.350 (2) Å | Cell parameters from 1641 reflections |
b = 13.916 (3) Å | θ = 2.5–21.2° |
c = 14.340 (3) Å | µ = 0.12 mm−1 |
α = 65.785 (4)° | T = 100 K |
β = 73.421 (4)° | Block, light yellow |
γ = 87.213 (5)° | 0.45 × 0.41 × 0.28 mm |
V = 1799.8 (7) Å3 |
Bruker APEX CCD area-detector diffractometer | 7051 independent reflections |
Radiation source: fine-focus sealed tube | 3529 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.092 |
Detector resolution: 8.3 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
phi and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −17→17 |
Tmin = 0.95, Tmax = 0.97 | l = −17→17 |
18938 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0125P)2] where P = (Fo2 + 2Fc2)/3 |
7051 reflections | (Δ/σ)max < 0.001 |
571 parameters | Δρmax = 0.71 e Å−3 |
13 restraints | Δρmin = −0.26 e Å−3 |
C12H10BNO5·0.67H2O | γ = 87.213 (5)° |
Mr = 271.03 | V = 1799.8 (7) Å3 |
Triclinic, P1 | Z = 6 |
a = 10.350 (2) Å | Mo Kα radiation |
b = 13.916 (3) Å | µ = 0.12 mm−1 |
c = 14.340 (3) Å | T = 100 K |
α = 65.785 (4)° | 0.45 × 0.41 × 0.28 mm |
β = 73.421 (4)° |
Bruker APEX CCD area-detector diffractometer | 7051 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3529 reflections with I > 2σ(I) |
Tmin = 0.95, Tmax = 0.97 | Rint = 0.092 |
18938 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 13 restraints |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.71 e Å−3 |
7051 reflections | Δρmin = −0.26 e Å−3 |
571 parameters |
Experimental. IR (KBr): 3520, 3370, 2950, 3024, 2942, 1648, 1615, 1562, 1480, 1305 and 786 cm-1. |
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. |
x | y | z | Uiso*/Ueq | ||
B1 | 0.9002 (3) | 0.3451 (3) | 0.2383 (3) | 0.0221 (9) | |
N1 | 0.8273 (3) | 0.4137 (2) | 0.4822 (2) | 0.0249 (7) | |
H1' | 0.837 (3) | 0.4691 (13) | 0.490 (2) | 0.037* | |
O1 | 0.83252 (17) | 0.25852 (15) | 0.23193 (14) | 0.0223 (5) | |
O2 | 0.86471 (17) | 0.45237 (15) | 0.16481 (14) | 0.0196 (5) | |
O3 | 0.82959 (17) | 0.55863 (15) | 0.01161 (15) | 0.0204 (5) | |
O4 | 0.76584 (19) | 0.30256 (15) | −0.15147 (16) | 0.0230 (5) | |
H4' | 0.752 (3) | 0.3656 (7) | −0.185 (2) | 0.034* | |
O5 | 1.04678 (19) | 0.34308 (16) | 0.20681 (14) | 0.0237 (5) | |
H5' | 1.083 (2) | 0.374 (2) | 0.1405 (4) | 0.036* | |
C1 | 0.8181 (3) | 0.2723 (3) | 0.1362 (2) | 0.0210 (8) | |
C2 | 0.8197 (2) | 0.3732 (2) | 0.0568 (2) | 0.0162 (7) | |
C3 | 0.8017 (2) | 0.3854 (2) | −0.0408 (2) | 0.0195 (7) | |
H3 | 0.8042 | 0.4540 | −0.0954 | 0.023* | |
C4 | 0.7803 (3) | 0.2968 (2) | −0.0568 (2) | 0.0189 (8) | |
C5 | 0.7774 (2) | 0.1964 (2) | 0.0234 (2) | 0.0195 (7) | |
H5 | 0.7624 | 0.1359 | 0.0118 | 0.023* | |
C6 | 0.7958 (3) | 0.1834 (2) | 0.1190 (2) | 0.0203 (8) | |
H6 | 0.7935 | 0.1145 | 0.1730 | 0.024* | |
C7 | 0.8381 (3) | 0.4674 (3) | 0.0756 (2) | 0.0207 (8) | |
C8 | 0.8476 (3) | 0.3359 (2) | 0.3585 (2) | 0.0204 (8) | |
C9 | 0.8663 (3) | 0.4209 (2) | 0.3818 (2) | 0.0258 (8) | |
H9 | 0.9080 | 0.4860 | 0.3250 | 0.031* | |
C10 | 0.7715 (3) | 0.3239 (3) | 0.5661 (2) | 0.0249 (8) | |
H10 | 0.7465 | 0.3211 | 0.6363 | 0.030* | |
C11 | 0.7504 (3) | 0.2356 (3) | 0.5504 (2) | 0.0252 (8) | |
H11 | 0.7115 | 0.1709 | 0.6093 | 0.030* | |
C12 | 0.7875 (3) | 0.2433 (2) | 0.4464 (2) | 0.0223 (8) | |
H12 | 0.7711 | 0.1830 | 0.4349 | 0.027* | |
B21 | −0.0548 (3) | 0.8085 (3) | 0.2594 (3) | 0.0228 (9) | |
N21 | −0.1361 (2) | 0.7302 (2) | 0.0507 (2) | 0.0203 (6) | |
H21' | −0.147 (3) | 0.6730 (11) | 0.046 (2) | 0.030* | |
O21 | −0.12591 (17) | 0.88671 (15) | 0.29523 (15) | 0.0223 (5) | |
O22 | −0.09568 (17) | 0.69622 (15) | 0.34851 (15) | 0.0217 (5) | |
O23 | −0.14161 (18) | 0.58725 (16) | 0.51874 (15) | 0.0241 (5) | |
O24 | −0.14430 (19) | 0.83893 (16) | 0.70031 (16) | 0.0263 (5) | |
H24' | −0.113 (3) | 0.7810 (11) | 0.729 (2) | 0.039* | |
O25 | 0.08854 (18) | 0.83243 (16) | 0.23529 (16) | 0.0241 (5) | |
H25' | 0.139 (2) | 0.7942 (19) | 0.210 (2) | 0.036* | |
C21 | −0.1338 (3) | 0.8719 (3) | 0.3963 (2) | 0.0206 (8) | |
C22 | −0.1302 (3) | 0.7722 (2) | 0.4743 (2) | 0.0178 (7) | |
C23 | −0.1363 (3) | 0.7592 (2) | 0.5777 (2) | 0.0212 (8) | |
H23 | −0.1352 | 0.6907 | 0.6312 | 0.025* | |
C24 | −0.1440 (3) | 0.8462 (2) | 0.6014 (2) | 0.0213 (8) | |
C25 | −0.1537 (3) | 0.9453 (2) | 0.5241 (2) | 0.0255 (8) | |
H25 | −0.1638 | 1.0045 | 0.5419 | 0.031* | |
C26 | −0.1489 (3) | 0.9593 (2) | 0.4221 (2) | 0.0245 (8) | |
H26 | −0.1559 | 1.0273 | 0.3701 | 0.029* | |
C27 | −0.1224 (3) | 0.6792 (3) | 0.4487 (2) | 0.0199 (8) | |
C28 | −0.0973 (3) | 0.8118 (2) | 0.1587 (2) | 0.0182 (7) | |
C29 | −0.1085 (3) | 0.7234 (2) | 0.1394 (2) | 0.0213 (8) | |
H29 | −0.0965 | 0.6561 | 0.1900 | 0.026* | |
C30 | −0.1534 (3) | 0.8226 (2) | −0.0245 (2) | 0.0212 (8) | |
H30 | −0.1701 | 0.8247 | −0.0871 | 0.025* | |
C31 | −0.1470 (3) | 0.9131 (2) | −0.0107 (2) | 0.0251 (8) | |
H31 | −0.1602 | 0.9790 | −0.0629 | 0.030* | |
C32 | −0.1203 (2) | 0.9070 (2) | 0.0823 (2) | 0.0216 (8) | |
H32 | −0.1180 | 0.9696 | 0.0934 | 0.026* | |
B41 | 0.5523 (3) | 0.5007 (3) | 0.7575 (3) | 0.0271 (10) | |
N41 | 0.5362 (3) | 0.7370 (3) | 0.8323 (2) | 0.0331 (7) | |
H41' | 0.549 (3) | 0.746 (3) | 0.8832 (17) | 0.050* | |
O41 | 0.47752 (18) | 0.48464 (17) | 0.69074 (15) | 0.0278 (6) | |
O42 | 0.49835 (18) | 0.42130 (17) | 0.87233 (15) | 0.0253 (5) | |
O43 | 0.44602 (18) | 0.25267 (16) | 0.98428 (16) | 0.0293 (6) | |
O44 | 0.4175 (2) | 0.07153 (18) | 0.74251 (18) | 0.0370 (6) | |
H44' | 0.452 (3) | 0.035 (2) | 0.7914 (17) | 0.056* | |
O45 | 0.69516 (18) | 0.47905 (17) | 0.72686 (15) | 0.0255 (5) | |
H45' | 0.743 (2) | 0.514 (2) | 0.6640 (8) | 0.038* | |
C41 | 0.4587 (3) | 0.3823 (3) | 0.7069 (2) | 0.0257 (8) | |
C42 | 0.4645 (3) | 0.2998 (3) | 0.8004 (2) | 0.0222 (8) | |
C43 | 0.4520 (3) | 0.1950 (3) | 0.8145 (2) | 0.0275 (8) | |
H43 | 0.4589 | 0.1389 | 0.8786 | 0.033* | |
C44 | 0.4293 (3) | 0.1734 (3) | 0.7338 (2) | 0.0257 (8) | |
C45 | 0.4154 (3) | 0.2559 (3) | 0.6422 (2) | 0.0277 (8) | |
H45 | 0.3957 | 0.2411 | 0.5884 | 0.033* | |
C46 | 0.4301 (3) | 0.3593 (3) | 0.6284 (2) | 0.0277 (8) | |
H46 | 0.4207 | 0.4153 | 0.5652 | 0.033* | |
C47 | 0.4713 (3) | 0.3225 (3) | 0.8912 (3) | 0.0275 (8) | |
C48 | 0.5329 (3) | 0.6165 (3) | 0.7528 (2) | 0.0245 (8) | |
C49 | 0.5463 (3) | 0.6392 (3) | 0.8358 (3) | 0.0300 (9) | |
H49 | 0.5629 | 0.5839 | 0.8965 | 0.036* | |
C50 | 0.5167 (3) | 0.8196 (3) | 0.7474 (3) | 0.0361 (9) | |
H50 | 0.5147 | 0.8887 | 0.7456 | 0.043* | |
C51 | 0.4998 (3) | 0.8035 (3) | 0.6645 (3) | 0.0350 (9) | |
H51 | 0.4834 | 0.8607 | 0.6050 | 0.042* | |
C52 | 0.5070 (3) | 0.7020 (3) | 0.6678 (2) | 0.0309 (9) | |
H52 | 0.4938 | 0.6907 | 0.6100 | 0.037* | |
O61 | 0.4664 (2) | 0.0441 (2) | 0.10850 (19) | 0.0460 (7) | |
H61A | 0.468 (3) | 0.1027 (14) | 0.0576 (19) | 0.069* | |
H61B | 0.3878 (13) | 0.028 (3) | 0.151 (2) | 0.069* | |
O62 | 0.2191 (2) | 0.98825 (19) | 0.24779 (19) | 0.0329 (6) | |
H62A | 0.175 (3) | 0.9429 (18) | 0.242 (3) | 0.049* | |
H62B | 0.175 (3) | 1.0343 (18) | 0.264 (2) | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
B1 | 0.024 (2) | 0.019 (2) | 0.021 (2) | −0.0021 (17) | −0.0106 (18) | −0.0041 (19) |
N1 | 0.0314 (16) | 0.026 (2) | 0.0243 (17) | 0.0072 (15) | −0.0157 (13) | −0.0130 (16) |
O1 | 0.0317 (12) | 0.0254 (14) | 0.0138 (13) | 0.0026 (10) | −0.0129 (10) | −0.0079 (10) |
O2 | 0.0264 (12) | 0.0219 (13) | 0.0147 (12) | 0.0037 (9) | −0.0125 (10) | −0.0075 (10) |
O3 | 0.0280 (12) | 0.0197 (13) | 0.0141 (12) | 0.0034 (10) | −0.0092 (10) | −0.0058 (11) |
O4 | 0.0318 (12) | 0.0257 (14) | 0.0190 (14) | 0.0090 (11) | −0.0165 (10) | −0.0112 (11) |
O5 | 0.0267 (13) | 0.0311 (15) | 0.0120 (12) | 0.0024 (10) | −0.0094 (10) | −0.0053 (11) |
C1 | 0.0194 (17) | 0.028 (2) | 0.0165 (19) | −0.0002 (15) | −0.0074 (14) | −0.0081 (17) |
C2 | 0.0154 (16) | 0.020 (2) | 0.0141 (18) | 0.0028 (14) | −0.0050 (14) | −0.0079 (16) |
C3 | 0.0164 (16) | 0.022 (2) | 0.0201 (19) | 0.0022 (14) | −0.0088 (14) | −0.0060 (16) |
C4 | 0.0155 (17) | 0.025 (2) | 0.0198 (19) | 0.0054 (15) | −0.0106 (14) | −0.0099 (17) |
C5 | 0.0207 (17) | 0.018 (2) | 0.022 (2) | 0.0044 (14) | −0.0067 (15) | −0.0103 (16) |
C6 | 0.0231 (17) | 0.021 (2) | 0.0157 (19) | 0.0023 (15) | −0.0076 (14) | −0.0057 (16) |
C7 | 0.0136 (17) | 0.032 (2) | 0.019 (2) | 0.0037 (15) | −0.0046 (14) | −0.0138 (18) |
C8 | 0.0208 (17) | 0.024 (2) | 0.022 (2) | 0.0052 (15) | −0.0130 (15) | −0.0097 (17) |
C9 | 0.0336 (19) | 0.033 (2) | 0.0109 (19) | 0.0014 (16) | −0.0128 (16) | −0.0048 (17) |
C10 | 0.0254 (18) | 0.033 (2) | 0.0141 (19) | 0.0068 (17) | −0.0088 (15) | −0.0067 (18) |
C11 | 0.0285 (18) | 0.028 (2) | 0.0155 (19) | −0.0004 (16) | −0.0064 (15) | −0.0049 (16) |
C12 | 0.0253 (18) | 0.024 (2) | 0.025 (2) | 0.0060 (15) | −0.0132 (15) | −0.0132 (17) |
B21 | 0.024 (2) | 0.022 (2) | 0.024 (2) | 0.0031 (18) | −0.0151 (18) | −0.0059 (19) |
N21 | 0.0208 (14) | 0.0213 (18) | 0.0225 (16) | 0.0019 (13) | −0.0085 (12) | −0.0112 (15) |
O21 | 0.0301 (12) | 0.0268 (14) | 0.0156 (13) | 0.0106 (10) | −0.0124 (10) | −0.0112 (11) |
O22 | 0.0255 (12) | 0.0278 (14) | 0.0134 (13) | 0.0019 (10) | −0.0085 (10) | −0.0083 (11) |
O23 | 0.0333 (12) | 0.0204 (14) | 0.0172 (13) | −0.0001 (10) | −0.0096 (10) | −0.0049 (11) |
O24 | 0.0406 (14) | 0.0272 (15) | 0.0187 (14) | 0.0121 (11) | −0.0180 (11) | −0.0116 (12) |
O25 | 0.0243 (13) | 0.0319 (15) | 0.0227 (13) | 0.0050 (10) | −0.0088 (10) | −0.0165 (11) |
C21 | 0.0207 (17) | 0.031 (2) | 0.018 (2) | 0.0040 (15) | −0.0108 (15) | −0.0150 (17) |
C22 | 0.0166 (16) | 0.023 (2) | 0.0174 (19) | 0.0023 (14) | −0.0094 (14) | −0.0089 (16) |
C23 | 0.0197 (17) | 0.025 (2) | 0.019 (2) | 0.0029 (15) | −0.0101 (14) | −0.0063 (16) |
C24 | 0.0224 (17) | 0.026 (2) | 0.020 (2) | 0.0059 (15) | −0.0123 (15) | −0.0098 (17) |
C25 | 0.0332 (19) | 0.027 (2) | 0.026 (2) | 0.0100 (16) | −0.0141 (16) | −0.0182 (18) |
C26 | 0.0324 (19) | 0.023 (2) | 0.019 (2) | 0.0080 (16) | −0.0134 (16) | −0.0072 (16) |
C27 | 0.0133 (16) | 0.032 (2) | 0.018 (2) | 0.0027 (15) | −0.0095 (15) | −0.0108 (18) |
C28 | 0.0168 (16) | 0.019 (2) | 0.0169 (19) | 0.0011 (14) | −0.0049 (14) | −0.0056 (16) |
C29 | 0.0225 (17) | 0.027 (2) | 0.0153 (19) | 0.0048 (15) | −0.0104 (14) | −0.0064 (16) |
C30 | 0.0248 (18) | 0.024 (2) | 0.0145 (19) | 0.0017 (15) | −0.0107 (15) | −0.0047 (16) |
C31 | 0.0281 (19) | 0.022 (2) | 0.025 (2) | 0.0031 (15) | −0.0127 (16) | −0.0069 (17) |
C32 | 0.0214 (17) | 0.022 (2) | 0.024 (2) | 0.0050 (14) | −0.0103 (15) | −0.0094 (16) |
B41 | 0.026 (2) | 0.035 (3) | 0.017 (2) | 0.0007 (19) | −0.0083 (18) | −0.006 (2) |
N41 | 0.0249 (16) | 0.041 (2) | 0.036 (2) | 0.0050 (14) | −0.0090 (15) | −0.0192 (18) |
O41 | 0.0315 (13) | 0.0310 (15) | 0.0220 (13) | 0.0021 (11) | −0.0159 (10) | −0.0066 (12) |
O42 | 0.0271 (12) | 0.0286 (15) | 0.0176 (13) | 0.0018 (11) | −0.0084 (10) | −0.0058 (11) |
O43 | 0.0302 (12) | 0.0322 (15) | 0.0197 (13) | −0.0023 (11) | −0.0093 (10) | −0.0033 (12) |
O44 | 0.0433 (15) | 0.0343 (17) | 0.0420 (17) | 0.0069 (12) | −0.0229 (12) | −0.0176 (14) |
O45 | 0.0239 (12) | 0.0344 (15) | 0.0157 (13) | 0.0035 (10) | −0.0053 (10) | −0.0084 (12) |
C41 | 0.0215 (18) | 0.030 (2) | 0.023 (2) | −0.0005 (16) | −0.0094 (15) | −0.0066 (18) |
C42 | 0.0211 (18) | 0.031 (2) | 0.017 (2) | 0.0017 (15) | −0.0104 (15) | −0.0086 (17) |
C43 | 0.0253 (18) | 0.030 (2) | 0.023 (2) | −0.0005 (16) | −0.0106 (16) | −0.0043 (17) |
C44 | 0.0223 (18) | 0.030 (2) | 0.023 (2) | 0.0009 (16) | −0.0073 (15) | −0.0087 (18) |
C45 | 0.0225 (18) | 0.038 (2) | 0.023 (2) | −0.0017 (17) | −0.0076 (15) | −0.0110 (18) |
C46 | 0.0229 (18) | 0.037 (2) | 0.021 (2) | 0.0050 (16) | −0.0109 (15) | −0.0067 (18) |
C47 | 0.0161 (18) | 0.031 (2) | 0.029 (2) | −0.0005 (16) | −0.0077 (16) | −0.0057 (19) |
C48 | 0.0181 (17) | 0.035 (2) | 0.020 (2) | 0.0043 (15) | −0.0048 (15) | −0.0120 (18) |
C49 | 0.0242 (19) | 0.035 (2) | 0.033 (2) | 0.0082 (17) | −0.0136 (16) | −0.0127 (19) |
C50 | 0.033 (2) | 0.031 (2) | 0.045 (3) | 0.0061 (17) | −0.0132 (19) | −0.015 (2) |
C51 | 0.037 (2) | 0.035 (3) | 0.033 (2) | 0.0121 (18) | −0.0164 (18) | −0.0112 (19) |
C52 | 0.0264 (19) | 0.038 (2) | 0.027 (2) | 0.0083 (17) | −0.0078 (16) | −0.0135 (19) |
O61 | 0.0400 (14) | 0.0447 (19) | 0.0402 (19) | 0.0037 (15) | −0.0133 (13) | −0.0038 (14) |
O62 | 0.0376 (15) | 0.0347 (18) | 0.0381 (15) | 0.0054 (12) | −0.0178 (12) | −0.0220 (13) |
B1—O1 | 1.469 (5) | C23—C24 | 1.379 (5) |
B1—O2 | 1.533 (3) | C24—C25 | 1.391 (3) |
B1—O5 | 1.456 (3) | C25—H25 | 0.950 |
B1—C8 | 1.604 (5) | C25—C26 | 1.381 (5) |
N1—H1' | 0.84 (3) | C26—H26 | 0.950 |
N1—C9 | 1.340 (4) | C28—C29 | 1.384 (5) |
N1—C10 | 1.334 (3) | C28—C32 | 1.392 (3) |
O1—C1 | 1.357 (4) | C29—H29 | 0.950 |
O2—C7 | 1.316 (4) | C30—H30 | 0.950 |
O3—C7 | 1.241 (3) | C30—C31 | 1.360 (5) |
O4—H4' | 0.840 (12) | C31—H31 | 0.950 |
O4—C4 | 1.377 (4) | C31—C32 | 1.406 (5) |
O5—H5' | 0.839 (6) | C32—H32 | 0.950 |
C1—C2 | 1.395 (3) | B41—O41 | 1.476 (5) |
C1—C6 | 1.398 (5) | B41—O42 | 1.512 (3) |
C2—C3 | 1.404 (4) | B41—O45 | 1.471 (3) |
C2—C7 | 1.474 (5) | B41—C48 | 1.590 (5) |
C3—H3 | 0.950 | N41—H41' | 0.84 (3) |
C3—C4 | 1.381 (5) | N41—C49 | 1.342 (5) |
C4—C5 | 1.392 (3) | N41—C50 | 1.347 (4) |
C5—H5 | 0.950 | O41—C41 | 1.359 (4) |
C5—C6 | 1.375 (4) | O42—C47 | 1.315 (4) |
C6—H6 | 0.950 | O43—C47 | 1.247 (3) |
C8—C9 | 1.390 (5) | O44—H44' | 0.84 (3) |
C8—C12 | 1.391 (3) | O44—C44 | 1.380 (4) |
C9—H9 | 0.950 | O45—H45' | 0.839 (11) |
C10—H10 | 0.950 | C41—C42 | 1.376 (4) |
C10—C11 | 1.374 (5) | C41—C46 | 1.397 (5) |
C11—H11 | 0.950 | C42—C43 | 1.395 (5) |
C11—C12 | 1.390 (4) | C42—C47 | 1.480 (6) |
C12—H12 | 0.950 | C43—H43 | 0.950 |
B21—O21 | 1.467 (4) | C43—C44 | 1.389 (5) |
B21—O22 | 1.539 (3) | C44—C45 | 1.384 (4) |
B21—O25 | 1.446 (4) | C45—H45 | 0.950 |
B21—C28 | 1.609 (5) | C45—C46 | 1.380 (5) |
N21—H21' | 0.84 (2) | C46—H46 | 0.950 |
N21—C29 | 1.346 (5) | C48—C49 | 1.393 (6) |
N21—C30 | 1.340 (3) | C48—C52 | 1.392 (4) |
O21—C21 | 1.355 (4) | C49—H49 | 0.950 |
O22—C27 | 1.302 (4) | C50—H50 | 0.950 |
O23—C27 | 1.242 (3) | C50—C51 | 1.353 (6) |
O24—H24' | 0.840 (18) | C51—H51 | 0.950 |
O24—C24 | 1.378 (4) | C51—C52 | 1.394 (5) |
O25—H25' | 0.84 (3) | C52—H52 | 0.950 |
C21—C22 | 1.386 (3) | O61—H61A | 0.840 (18) |
C21—C26 | 1.399 (5) | O61—H61B | 0.840 (14) |
C22—C23 | 1.400 (4) | O62—H62A | 0.84 (3) |
C22—C27 | 1.475 (5) | O62—H62B | 0.84 (3) |
C23—H23 | 0.950 | ||
O1—B1—O2 | 110.5 (3) | C24—C25—C26 | 121.3 (3) |
O1—B1—O5 | 112 (3) | H25—C25—C26 | 119.0 |
O1—B1—C8 | 108.9 (3) | C21—C26—C25 | 119.1 (3) |
O2—B1—O5 | 107.9 (3) | C21—C26—H26 | 120.0 |
O2—B1—C8 | 107.8 (3) | C25—C26—H26 | 120.0 |
O5—B1—C8 | 109.8 (3) | O22—C27—O23 | 120.0 (4) |
H1'—N1—C9 | 117 (1) | O22—C27—C22 | 117.6 (3) |
H1'—N1—C10 | 120 (1) | O23—C27—C22 | 122.4 (3) |
C9—N1—C10 | 122.3 (3) | B21—C28—C29 | 123.4 (3) |
B1—O1—C1 | 118.5 (2) | B21—C28—C32 | 120.9 (3) |
B1—O2—C7 | 122.4 (2) | C29—C28—C32 | 115.7 (3) |
H4'—O4—C4 | 106 (2) | N21—C29—C28 | 121.7 (3) |
B1—O5—H5' | 113.5 (6) | N21—C29—H29 | 119.0 |
O1—C1—C2 | 121.3 (3) | C28—C29—H29 | 119.0 |
O1—C1—C6 | 119.0 (3) | N21—C30—H30 | 120.0 |
C2—C1—C6 | 119.7 (3) | N21—C30—C31 | 119.8 (3) |
C1—C2—C3 | 120.2 (3) | H30—C30—C31 | 120.0 |
C1—C2—C7 | 120.1 (3) | C30—C31—H31 | 121.0 |
C3—C2—C7 | 119.7 (3) | C30—C31—C32 | 118.5 (3) |
C2—C3—H3 | 120.0 | H31—C31—C32 | 121.0 |
C2—C3—C4 | 119.4 (3) | C28—C32—C31 | 121.9 (3) |
H3—C3—C4 | 120.0 | C28—C32—H32 | 119.0 |
O4—C4—C3 | 122.7 (3) | C31—C32—H32 | 119.0 |
O4—C4—C5 | 117.3 (3) | O41—B41—O42 | 110.4 (3) |
C3—C4—C5 | 120.0 (3) | O41—B41—O45 | 111.9 (3) |
C4—C5—H5 | 119.0 | O41—B41—C48 | 108.8 (3) |
C4—C5—C6 | 121.2 (3) | O42—B41—O45 | 103.7 (3) |
H5—C5—C6 | 119.0 | O42—B41—C48 | 108.9 (3) |
C1—C6—C5 | 119.6 (3) | O45—B41—C48 | 113.1 (3) |
C1—C6—H6 | 120.0 | H41'—N41—C49 | 117 (2) |
C5—C6—H6 | 120.0 | H41'—N41—C50 | 120 (2) |
O2—C7—O3 | 119.5 (3) | C49—N41—C50 | 122.2 (4) |
O2—C7—C2 | 117.5 (3) | B41—O41—C41 | 114.8 (3) |
O3—C7—C2 | 123.0 (3) | B41—O42—C47 | 118.5 (3) |
B1—C8—C9 | 121.0 (3) | H44'—O44—C44 | 104 (2) |
B1—C8—C12 | 123.6 (3) | B41—O45—H45' | 119 (1) |
C9—C8—C12 | 115.3 (3) | O41—C41—C42 | 121.5 (3) |
N1—C9—C8 | 121.9 (3) | O41—C41—C46 | 119.8 (3) |
N1—C9—H9 | 119.0 | C42—C41—C46 | 118.6 (3) |
C8—C9—H9 | 119.0 | C41—C42—C43 | 121.3 (3) |
N1—C10—H10 | 120.0 | C41—C42—C47 | 119.2 (3) |
N1—C10—C11 | 119.7 (3) | C43—C42—C47 | 119.2 (3) |
H10—C10—C11 | 120.0 | C42—C43—H43 | 120.0 |
C10—C11—H11 | 120.0 | C42—C43—C44 | 119.3 (3) |
C10—C11—C12 | 118.4 (3) | H43—C43—C44 | 120.0 |
H11—C11—C12 | 120.0 | O44—C44—C43 | 122 (3) |
C8—C12—C11 | 122.4 (3) | O44—C44—C45 | 118.3 (3) |
C8—C12—H12 | 119.0 | C43—C44—C45 | 119.7 (3) |
C11—C12—H12 | 119.0 | C44—C45—H45 | 120.0 |
O21—B21—O22 | 110.4 (3) | C44—C45—C46 | 120.5 (3) |
O21—B21—O25 | 107.4 (3) | H45—C45—C46 | 120.0 |
O21—B21—C28 | 109.5 (3) | C41—C46—C45 | 120.5 (3) |
O22—B21—O25 | 109.1 (3) | C41—C46—H46 | 120.0 |
O22—B21—C28 | 107.3 (2) | C45—C46—H46 | 120.0 |
O25—B21—C28 | 113.1 (3) | O42—C47—O43 | 119.8 (3) |
H21'—N21—C29 | 116 (1) | O42—C47—C42 | 117.8 (3) |
H21'—N21—C30 | 121 (1) | O43—C47—C42 | 122.4 (3) |
C29—N21—C30 | 122.4 (3) | B41—C48—C49 | 120.2 (3) |
B21—O21—C21 | 115.9 (3) | B41—C48—C52 | 124.5 (3) |
B21—O22—C27 | 120.9 (2) | C49—C48—C52 | 115.2 (3) |
H24'—O24—C24 | 105 (2) | N41—C49—C48 | 121.8 (4) |
B21—O25—H25' | 114 (2) | N41—C49—H49 | 119.0 |
O21—C21—C22 | 121.4 (3) | C48—C49—H49 | 119.0 |
O21—C21—C26 | 118.8 (3) | N41—C50—H50 | 120.0 |
C22—C21—C26 | 119.8 (3) | N41—C50—C51 | 119.5 (3) |
C21—C22—C23 | 120.3 (3) | H50—C50—C51 | 120.0 |
C21—C22—C27 | 119.8 (3) | C50—C51—H51 | 120.0 |
C23—C22—C27 | 119.9 (3) | C50—C51—C52 | 119.1 (4) |
C22—C23—H23 | 120.0 | H51—C51—C52 | 120.0 |
C22—C23—C24 | 119.8 (3) | C48—C52—C51 | 122.2 (3) |
H23—C23—C24 | 120.0 | C48—C52—H52 | 119.0 |
O24—C24—C23 | 122.4 (3) | C51—C52—H52 | 119.0 |
O24—C24—C25 | 118.1 (3) | H61A—O61—H61B | 108 (3) |
C23—C24—C25 | 119.5 (3) | H62A—O62—H62B | 116 (3) |
C24—C25—H25 | 119.0 | ||
O5—B1—O1—C1 | −84.3 (3) | B21—O22—C27—O23 | −172.6 (2) |
O2—B1—O1—C1 | 36.0 (3) | B21—O22—C27—C22 | 8.1 (3) |
C8—B1—O1—C1 | 154.2 (2) | C21—C22—C27—O23 | −167.6 (2) |
O5—B1—O2—C7 | 92.1 (3) | C23—C22—C27—O23 | 11.3 (4) |
O1—B1—O2—C7 | −30.6 (3) | C21—C22—C27—O22 | 11.6 (4) |
C8—B1—O2—C7 | −149.4 (2) | C23—C22—C27—O22 | −169.5 (2) |
B1—O1—C1—C2 | −23.2 (4) | O25—B21—C28—C29 | 94.2 (3) |
B1—O1—C1—C6 | 159.4 (2) | O21—B21—C28—C29 | −146.0 (3) |
O1—C1—C2—C3 | −178.6 (2) | O22—B21—C28—C29 | −26.2 (4) |
C6—C1—C2—C3 | −1.3 (4) | O25—B21—C28—C32 | −83.3 (3) |
O1—C1—C2—C7 | 0.4 (4) | O21—B21—C28—C32 | 36.4 (4) |
C6—C1—C2—C7 | 177.8 (2) | O22—B21—C28—C32 | 156.3 (2) |
C1—C2—C3—C4 | 1.0 (4) | C30—N21—C29—C28 | 0.5 (4) |
C7—C2—C3—C4 | −178.0 (2) | C32—C28—C29—N21 | 1.9 (4) |
C2—C3—C4—O4 | −178.0 (2) | B21—C28—C29—N21 | −175.8 (3) |
C2—C3—C4—C5 | −0.3 (4) | C29—N21—C30—C31 | −1.8 (4) |
O4—C4—C5—C6 | 177.7 (2) | N21—C30—C31—C32 | 0.8 (4) |
C3—C4—C5—C6 | −0.1 (4) | C29—C28—C32—C31 | −2.9 (4) |
C4—C5—C6—C1 | −0.1 (4) | B21—C28—C32—C31 | 174.8 (2) |
O1—C1—C6—C5 | 178.2 (2) | C30—C31—C32—C28 | 1.6 (4) |
C2—C1—C6—C5 | 0.8 (4) | O45—B41—O41—C41 | 69.1 (3) |
B1—O2—C7—O3 | −169.4 (2) | O42—B41—O41—C41 | −45.8 (3) |
B1—O2—C7—C2 | 10.5 (4) | C48—B41—O41—C41 | −165.2 (2) |
C1—C2—C7—O3 | −174.1 (2) | O45—B41—O42—C47 | −77.1 (3) |
C3—C2—C7—O3 | 4.9 (4) | O41—B41—O42—C47 | 42.8 (4) |
C1—C2—C7—O2 | 6.0 (4) | C48—B41—O42—C47 | 162.2 (2) |
C3—C2—C7—O2 | −175.0 (2) | B41—O41—C41—C42 | 21.8 (4) |
O5—B1—C8—C9 | 74.1 (3) | B41—O41—C41—C46 | −159.4 (3) |
O1—B1—C8—C9 | −163.0 (2) | O41—C41—C42—C43 | −176.7 (3) |
O2—B1—C8—C9 | −43.1 (3) | C46—C41—C42—C43 | 4.6 (4) |
O5—B1—C8—C12 | −102.5 (3) | O41—C41—C42—C47 | 9.1 (4) |
O1—B1—C8—C12 | 20.4 (4) | C46—C41—C42—C47 | −169.7 (3) |
O2—B1—C8—C12 | 140.3 (3) | C41—C42—C43—C44 | −1.9 (4) |
C10—N1—C9—C8 | 1.8 (4) | C47—C42—C43—C44 | 172.4 (3) |
C12—C8—C9—N1 | −0.8 (4) | C42—C43—C44—O44 | 179.3 (3) |
B1—C8—C9—N1 | −177.6 (3) | C42—C43—C44—C45 | −1.9 (4) |
C9—N1—C10—C11 | −1.2 (4) | O44—C44—C45—C46 | −178.2 (2) |
N1—C10—C11—C12 | −0.5 (4) | C43—C44—C45—C46 | 3.0 (4) |
C10—C11—C12—C8 | 1.6 (4) | C44—C45—C46—C41 | −0.2 (4) |
C9—C8—C12—C11 | −0.9 (4) | O41—C41—C46—C45 | 177.7 (2) |
B1—C8—C12—C11 | 175.9 (3) | C42—C41—C46—C45 | −3.5 (4) |
O25—B21—O21—C21 | −76.3 (3) | B41—O42—C47—O43 | 169.5 (2) |
O22—B21—O21—C21 | 42.6 (3) | B41—O42—C47—C42 | −14.0 (4) |
C28—B21—O21—C21 | 160.5 (2) | C41—C42—C47—O43 | 163.3 (3) |
O25—B21—O22—C27 | 83.4 (3) | C43—C42—C47—O43 | −11.1 (4) |
O21—B21—O22—C27 | −34.4 (3) | C41—C42—C47—O42 | −13.1 (4) |
C28—B21—O22—C27 | −153.7 (2) | C43—C42—C47—O42 | 172.5 (2) |
B21—O21—C21—C22 | −26.6 (4) | O45—B41—C48—C52 | 98.1 (3) |
B21—O21—C21—C26 | 154.9 (3) | O41—B41—C48—C52 | −26.9 (4) |
O21—C21—C22—C23 | 179.0 (2) | O42—B41—C48—C52 | −147.2 (3) |
C26—C21—C22—C23 | −2.5 (4) | O45—B41—C48—C49 | −79.6 (4) |
O21—C21—C22—C27 | −2.1 (4) | O41—B41—C48—C49 | 155.4 (3) |
C26—C21—C22—C27 | 176.4 (2) | O42—B41—C48—C49 | 35.0 (4) |
C21—C22—C23—C24 | −0.9 (4) | C50—N41—C49—C48 | −2.0 (5) |
C27—C22—C23—C24 | −179.8 (3) | C52—C48—C49—N41 | −0.8 (4) |
C22—C23—C24—O24 | −177.1 (2) | B41—C48—C49—N41 | 177.2 (3) |
C22—C23—C24—C25 | 3.8 (4) | C49—N41—C50—C51 | 3.3 (5) |
O24—C24—C25—C26 | 177.5 (2) | N41—C50—C51—C52 | −1.8 (5) |
C23—C24—C25—C26 | −3.3 (4) | C50—C51—C52—C48 | −1.0 (5) |
C24—C25—C26—C21 | −0.1 (4) | C49—C48—C52—C51 | 2.2 (4) |
O21—C21—C26—C25 | −178.4 (2) | B41—C48—C52—C51 | −175.6 (3) |
C22—C21—C26—C25 | 3.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O62—H62A···O25 | 0.84 | 1.86 | 2.702 (4) | 174 |
O45—H45′···O23i | 0.84 | 1.94 | 2.777 (2) | 177 |
O4—H4′···O45ii | 0.84 | 1.77 | 2.579 (3) | 162 |
O61—H61A···O43ii | 0.84 | 1.95 | 2.749 (3) | 159 |
O5—H5′···O3iii | 0.84 | 1.93 | 2.773 (2) | 178 |
O24—H24′···O5iv | 0.84 | 1.8 | 2.638 (3) | 179 |
O25—H25′···O4v | 0.84 | 1.95 | 2.791 (3) | 173 |
O62—H62B···O24vi | 0.84 | 2.02 | 2.810 (4) | 157 |
O44—H44′···O61vii | 0.84 | 1.82 | 2.656 (3) | 177 |
O61—H61B···O62viii | 0.84 | 1.83 | 2.673 (3) | 178 |
N1—H1′···O23i | 0.84 | 1.89 | 2.725 (4) | 176 |
N21—H21′···O3ix | 0.84 | 1.89 | 2.727 (4) | 170 |
N41—H41′···O43x | 0.84 | 1.92 | 2.749 (5) | 169 |
C11—H11···O62iv | 0.95 | 2.57 | 3.348 (4) | 140 |
C23—H23···O5iv | 0.95 | 2.59 | 3.215 (4) | 123 |
C43—H43···O61vii | 0.95 | 2.57 | 3.201 (4) | 124 |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z−1; (iii) −x+2, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z; (vi) −x, −y+2, −z+1; (vii) −x+1, −y, −z+1; (viii) x, y−1, z; (ix) x−1, y, z; (x) −x+1, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O62—H62A···O25 | 0.84 | 1.86 | 2.702 (4) | 174 |
O45—H45'···O23i | 0.84 | 1.94 | 2.777 (2) | 177 |
O4—H4'···O45ii | 0.84 | 1.77 | 2.579 (3) | 162 |
O61—H61A···O43ii | 0.84 | 1.95 | 2.749 (3) | 159 |
O5—H5'···O3iii | 0.84 | 1.93 | 2.773 (2) | 178 |
O24—H24'···O5iv | 0.84 | 1.8 | 2.638 (3) | 179 |
O25—H25'···O4v | 0.84 | 1.95 | 2.791 (3) | 173 |
O62—H62B···O24vi | 0.84 | 2.02 | 2.810 (4) | 157 |
O44—H44'···O61vii | 0.84 | 1.82 | 2.656 (3) | 177 |
O61—H61B···O62viii | 0.84 | 1.83 | 2.673 (3) | 178 |
N1—H1'···O23i | 0.84 | 1.89 | 2.725 (4) | 176 |
N21—H21'···O3ix | 0.84 | 1.89 | 2.727 (4) | 170 |
N41—H41'···O43x | 0.84 | 1.92 | 2.749 (5) | 169 |
C11—H11···O62iv | 0.95 | 2.57 | 3.348 (4) | 140 |
C23—H23···O5iv | 0.95 | 2.59 | 3.215 (4) | 123 |
C43—H43···O61vii | 0.95 | 2.57 | 3.201 (4) | 124 |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z−1; (iii) −x+2, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z; (vi) −x, −y+2, −z+1; (vii) −x+1, −y, −z+1; (viii) x, y−1, z; (ix) x−1, y, z; (x) −x+1, −y+1, −z+2. |
Acknowledgements
This work was supported financially by the Consejo Nacional de Ciencia y Tecnología (CONACyT, project No. 177616). The authors gratefully acknowledge access to the X-ray facilities in the Chemical Research Center at the Autonomous State University of Morelos (CIQ–UAEM).
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The O—H groups of boronic acids are able to react with alcohols to give boronic esters through the formation of covalent B–O bonds (Fujita et al., 2008). The high thermodynamic stability of boronic esters has been employed for the formation of cyclo-oligomeric and polymeric boron compounds with potential applications in gas storage and separation (Höpfl et al., 2002; Severin et al., 2009). Herein, we report on the solid-state structure of a new boronic ester formed between 2,5-dihydroxybenzoic acid and 3-pyridine boronic acid.
The molecular components of the title compound, 6-hydroxy-2-(pyridinium-3-yl)-4H-benzo-1,3,2-dioxaborininato-4-one) 0.67-hydrate, are shown in Fig. 1. The asymmetric unit contains three crystallographically independent ester molecules with similar conformations and two water molecules. The six-membered heterocyclic rings in the boronic esters have half-chair conformations, and the deviation of the B atom from the boronate mean planes range from 0.456 (3) to 0.657 (3) Å. The B atoms have tetrahedral coordination environments with B—O and B—C bond distances of 1.446 (4)–1.539 (3) Å and 1.590 (5)–1.609 (5) Å, respectively. The tetrahedral character of the boron atoms was evidenced also by 11B-NMR spectroscopy, giving a chemical shift of 3.8 p.p.m. (Barba et al., 2010). In the crystal, the molecular entities are linked into a three-dimensional network by a large number of O—H···O and N+—H···-O hydrogen bonds. Crystal packing is accomplished by additional C—H···O and π–π contacts (Table 1 and Fig 2), of which the latter are formed between pyridinium and phenyl rings. The centroid-centroid distances are Cg1···Cg2i = 3.774 (4) Å, Cg1···Cg4ii = 3.787 (4) Å and Cg2···Cg3iii = 3.621 (4) Å, where Cg1, Cg2, Cg3 and Cg4 are the centroids of C1–C6, N21/C28–C32, C41–C46 and N41/C48–C52 rings, respectively. [symmetry codes: (i) 1 - x, 1 - y, -z; (ii) 1 - x, 1 - y, 1 - z; (iii) -x, 1 - y, 1 - z.]