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In the title compounds, 3-(dihydroxyboryl)anilinium bisulfate monohydrate, C
6H
9BNO
2+·HSO
4−·H
2O (
I), and 3-(dihydroxyboryl)anilinium methyl sulfate, C
6H
9BNO
2+·CH
3SO
4− (
II), the almost planar boronic acid molecules are linked by pairs of O—H
O hydrogen bonds, forming centrosymmetric motifs that can be described by the graph-set
R22(8) motif. In both crystals, the B(OH)
2 group acquires a
syn–
anti conformation (with respect to the H atoms). The presence of the hydrogen-bonding functional groups B(OH)
2, NH
3+, HSO
4−, CH
3SO
4− and H
2O generates three-dimensional hydrogen-bonded networks, in which the bisulfate (HSO
4−) and methyl sulfate (CH
3SO
4−) counter-ions act as the central building blocks within the crystal structures. Furthermore, in both structures, the packing is stabilized by weak boron–π interactions, as shown by noncovalent interactions (NCI) index calculations.
Supporting information
CCDC references: 2268110; 2268109
For both structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
3-(Dihydroxyboryl)anilinium hydrogen sulfate monohydrate (I)
top
Crystal data top
C6H9BNO2+·HSO4−·H2O | Dx = 1.582 Mg m−3 |
Mr = 253.04 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, Pbca | Cell parameters from 2687 reflections |
a = 14.1807 (6) Å | θ = 4.3–72.3° |
b = 7.4675 (3) Å | µ = 2.96 mm−1 |
c = 20.0702 (8) Å | T = 293 K |
V = 2125.32 (15) Å3 | Block, clear yellowish yellow |
Z = 8 | 0.34 × 0.2 × 0.16 mm |
F(000) = 1056 | |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 1914 reflections with I > 2σ(I) |
Detector resolution: 8.0769 pixels mm-1 | Rint = 0.040 |
ω scans | θmax = 72.7°, θmin = 4.4° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −17→9 |
Tmin = 0.589, Tmax = 1.000 | k = −9→7 |
4648 measured reflections | l = −23→24 |
2071 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.0922P)2 + 0.8783P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2071 reflections | Δρmax = 0.74 e Å−3 |
177 parameters | Δρmin = −0.82 e Å−3 |
8 restraints | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.39986 (14) | 0.5777 (3) | 0.55191 (9) | 0.0136 (4) | |
C2 | 0.40815 (14) | 0.5262 (3) | 0.61859 (9) | 0.0134 (4) | |
H2 | 0.435219 | 0.603948 | 0.649307 | 0.016* | |
C3 | 0.37619 (14) | 0.3597 (3) | 0.63916 (9) | 0.0130 (4) | |
C4 | 0.33477 (16) | 0.2402 (3) | 0.59484 (11) | 0.0165 (4) | |
H4 | 0.313501 | 0.128960 | 0.609284 | 0.020* | |
C5 | 0.32584 (16) | 0.2906 (3) | 0.52852 (10) | 0.0180 (4) | |
H5 | 0.298259 | 0.212551 | 0.498100 | 0.022* | |
C6 | 0.35800 (14) | 0.4573 (3) | 0.50738 (10) | 0.0153 (4) | |
H6 | 0.351547 | 0.489258 | 0.462826 | 0.018* | |
B1 | 0.43950 (17) | 0.7658 (3) | 0.53047 (12) | 0.0142 (5) | |
N1 | 0.38825 (13) | 0.3073 (2) | 0.70905 (8) | 0.0136 (4) | |
H1D | 0.4285 (14) | 0.222 (2) | 0.7134 (13) | 0.019 (7)* | |
H1B | 0.3392 (11) | 0.264 (3) | 0.7284 (12) | 0.015 (6)* | |
H1C | 0.405 (2) | 0.394 (2) | 0.7347 (12) | 0.032 (8)* | |
O1 | 0.49180 (11) | 0.8560 (2) | 0.57635 (7) | 0.0180 (4) | |
H1A | 0.509 (3) | 0.953 (2) | 0.5618 (15) | 0.055 (11)* | |
O2 | 0.42498 (11) | 0.8431 (2) | 0.46978 (7) | 0.0180 (4) | |
H2A | 0.3939 (17) | 0.791 (3) | 0.4412 (10) | 0.026 (7)* | |
O3 | 0.31753 (11) | 0.7391 (2) | 0.36457 (7) | 0.0165 (4) | |
O4 | 0.43779 (11) | 0.8888 (2) | 0.29739 (7) | 0.0179 (4) | |
O5 | 0.28937 (11) | 0.8106 (2) | 0.24853 (7) | 0.0205 (4) | |
O6 | 0.40248 (11) | 0.5799 (2) | 0.27829 (8) | 0.0214 (4) | |
H6A | 0.390 (3) | 0.510 (4) | 0.3084 (12) | 0.073 (14)* | |
O7 | 0.37303 (11) | 0.3040 (2) | 0.34654 (8) | 0.0182 (4) | |
H7A | 0.4087 (18) | 0.257 (4) | 0.3736 (12) | 0.036 (9)* | |
H7B | 0.3234 (12) | 0.270 (4) | 0.3633 (15) | 0.045 (11)* | |
S1 | 0.35902 (4) | 0.76286 (7) | 0.29823 (2) | 0.0129 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0127 (10) | 0.0194 (10) | 0.0086 (9) | 0.0008 (7) | 0.0001 (6) | −0.0002 (7) |
C2 | 0.0118 (9) | 0.0203 (10) | 0.0080 (9) | −0.0004 (7) | 0.0001 (6) | −0.0019 (7) |
C3 | 0.0106 (9) | 0.0208 (10) | 0.0077 (9) | 0.0008 (7) | 0.0011 (7) | 0.0021 (7) |
C4 | 0.0163 (10) | 0.0198 (10) | 0.0135 (10) | −0.0030 (7) | 0.0006 (9) | 0.0006 (7) |
C5 | 0.0196 (11) | 0.0233 (10) | 0.0110 (9) | −0.0048 (9) | −0.0008 (8) | −0.0032 (8) |
C6 | 0.0171 (10) | 0.0218 (10) | 0.0072 (9) | −0.0004 (7) | −0.0008 (7) | −0.0001 (7) |
B1 | 0.0132 (11) | 0.0203 (11) | 0.0092 (10) | 0.0000 (8) | −0.0011 (9) | −0.0005 (8) |
N1 | 0.0129 (8) | 0.0198 (9) | 0.0081 (8) | −0.0009 (7) | 0.0007 (6) | 0.0022 (6) |
O1 | 0.0233 (8) | 0.0199 (7) | 0.0109 (7) | −0.0057 (6) | −0.0053 (6) | 0.0033 (5) |
O2 | 0.0225 (8) | 0.0220 (8) | 0.0095 (7) | −0.0063 (6) | −0.0054 (6) | 0.0021 (6) |
O3 | 0.0158 (8) | 0.0265 (8) | 0.0072 (7) | 0.0007 (6) | −0.0006 (5) | −0.0002 (5) |
O4 | 0.0135 (8) | 0.0196 (8) | 0.0207 (8) | −0.0028 (6) | −0.0018 (5) | 0.0021 (5) |
O5 | 0.0147 (7) | 0.0357 (9) | 0.0111 (7) | −0.0034 (7) | −0.0028 (6) | 0.0049 (6) |
O6 | 0.0243 (8) | 0.0210 (8) | 0.0187 (8) | −0.0005 (6) | 0.0081 (6) | −0.0007 (6) |
O7 | 0.0173 (8) | 0.0243 (8) | 0.0130 (7) | −0.0006 (6) | −0.0021 (6) | 0.0031 (6) |
S1 | 0.0114 (3) | 0.0192 (3) | 0.0083 (3) | −0.00132 (17) | −0.00057 (15) | 0.00027 (16) |
Geometric parameters (Å, º) top
C1—C2 | 1.397 (3) | B1—O2 | 1.364 (3) |
C1—C6 | 1.400 (3) | N1—H1D | 0.8600 (10) |
C1—B1 | 1.573 (3) | N1—H1B | 0.8600 (11) |
C2—H2 | 0.9300 | N1—H1C | 0.8601 (11) |
C2—C3 | 1.386 (3) | O1—H1A | 0.8200 (11) |
C3—C4 | 1.390 (3) | O2—H2A | 0.8200 (11) |
C3—N1 | 1.466 (2) | O3—S1 | 1.4665 (15) |
C4—H4 | 0.9300 | O4—S1 | 1.4604 (16) |
C4—C5 | 1.389 (3) | O5—S1 | 1.4482 (15) |
C5—H5 | 0.9300 | O6—H6A | 0.8200 (10) |
C5—C6 | 1.392 (3) | O6—S1 | 1.5510 (16) |
C6—H6 | 0.9300 | O7—H7A | 0.8200 (10) |
B1—O1 | 1.361 (3) | O7—H7B | 0.8200 (11) |
| | | |
C2—C1—C6 | 118.06 (19) | O1—B1—O2 | 118.48 (19) |
C2—C1—B1 | 118.54 (18) | O2—B1—C1 | 124.66 (19) |
C6—C1—B1 | 123.39 (18) | C3—N1—H1D | 111.9 (18) |
C1—C2—H2 | 119.9 | C3—N1—H1B | 116.0 (18) |
C3—C2—C1 | 120.30 (18) | C3—N1—H1C | 113.9 (19) |
C3—C2—H2 | 119.9 | H1D—N1—H1B | 102 (2) |
C2—C3—C4 | 121.55 (18) | H1D—N1—H1C | 108 (3) |
C2—C3—N1 | 119.06 (18) | H1B—N1—H1C | 104 (3) |
C4—C3—N1 | 119.38 (19) | B1—O1—H1A | 111 (2) |
C3—C4—H4 | 120.7 | B1—O2—H2A | 120 (2) |
C5—C4—C3 | 118.55 (19) | S1—O6—H6A | 107 (3) |
C5—C4—H4 | 120.7 | H7A—O7—H7B | 97 (3) |
C4—C5—H5 | 119.9 | O3—S1—O6 | 106.70 (9) |
C4—C5—C6 | 120.29 (19) | O4—S1—O3 | 113.27 (9) |
C6—C5—H5 | 119.9 | O4—S1—O6 | 105.09 (9) |
C1—C6—H6 | 119.4 | O5—S1—O3 | 112.42 (9) |
C5—C6—C1 | 121.24 (18) | O5—S1—O4 | 110.81 (9) |
C5—C6—H6 | 119.4 | O5—S1—O6 | 108.05 (10) |
O1—B1—C1 | 116.85 (18) | | |
| | | |
C1—C2—C3—C4 | −0.4 (3) | C4—C5—C6—C1 | 0.0 (3) |
C1—C2—C3—N1 | 178.29 (18) | C6—C1—C2—C3 | 0.5 (3) |
C2—C1—C6—C5 | −0.3 (3) | C6—C1—B1—O1 | −169.55 (19) |
C2—C1—B1—O1 | 9.3 (3) | C6—C1—B1—O2 | 10.5 (3) |
C2—C1—B1—O2 | −170.6 (2) | B1—C1—C2—C3 | −178.42 (18) |
C2—C3—C4—C5 | 0.1 (3) | B1—C1—C6—C5 | 178.56 (19) |
C3—C4—C5—C6 | 0.1 (3) | N1—C3—C4—C5 | −178.59 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1D···O4i | 0.86 (2) | 2.08 (1) | 2.872 (2) | 153 (1) |
N1—H1B···O5ii | 0.86 (2) | 1.95 (1) | 2.783 (2) | 163 (2) |
N1—H1B···O7iii | 0.86 (2) | 2.47 (2) | 2.89 (2) | 111 (1) |
N1—H1C···O4iv | 0.86 (2) | 2.11 (1) | 2.964 (2) | 177 (3) |
O1—H1A···O2v | 0.82 (2) | 1.90 (3) | 2.702 (2) | 168 (4) |
O2—H2A···O3 | 0.82 (2) | 1.92 (2) | 2.717 (2) | 163 (2) |
O6—H6A···O7 | 0.82 (3) | 1.74 (3) | 2.509 (2) | 157 (3) |
O7—H7A···O1i | 0.82 (3) | 1.93 (3) | 2.738 (2) | 170 (2) |
O7—H7B···O3vi | 0.82 (2) | 2.01 (1) | 2.769 (2) | 153 (3) |
C2—H2···O1 | 0.93 | 2.52 | 2.862 (3) | 102 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, −y+1, z+1/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z+1/2; (v) −x+1, −y+2, −z+1; (vi) −x+1/2, y−1/2, z. |
3-(Dihydroxyboryl)anilinium methyl sulfate (II)
top
Crystal data top
C6H9BNO2+·CH3SO4− | F(000) = 520 |
Mr = 249.05 | Dx = 1.582 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 10.97561 (18) Å | Cell parameters from 2836 reflections |
b = 7.22452 (11) Å | θ = 5.9–72.5° |
c = 13.5494 (2) Å | µ = 2.93 mm−1 |
β = 103.3430 (15)° | T = 293 K |
V = 1045.38 (3) Å3 | Plate, clear yellowish yellow |
Z = 4 | 0.34 × 0.3 × 0.14 mm |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 1965 reflections with I > 2σ(I) |
Detector resolution: 8.0769 pixels mm-1 | Rint = 0.014 |
ω scans | θmax = 72.8°, θmin = 4.7° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −12→13 |
Tmin = 0.726, Tmax = 1.000 | k = −8→6 |
3631 measured reflections | l = −16→15 |
2017 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.0367P)2 + 0.659P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
2017 reflections | Δρmax = 0.35 e Å−3 |
166 parameters | Δρmin = −0.40 e Å−3 |
5 restraints | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.96725 (14) | 0.5585 (2) | 0.36273 (11) | 0.0132 (3) | |
C2 | 1.05927 (14) | 0.5033 (2) | 0.31245 (11) | 0.0131 (3) | |
H2 | 1.127996 | 0.579241 | 0.313674 | 0.016* | |
C3 | 1.04875 (14) | 0.3366 (2) | 0.26100 (11) | 0.0129 (3) | |
C4 | 0.94961 (15) | 0.2183 (2) | 0.25800 (12) | 0.0173 (3) | |
H4 | 0.944115 | 0.106501 | 0.223217 | 0.021* | |
C5 | 0.85795 (16) | 0.2701 (2) | 0.30822 (13) | 0.0214 (4) | |
H5 | 0.790476 | 0.191837 | 0.307551 | 0.026* | |
C6 | 0.86641 (15) | 0.4380 (2) | 0.35948 (12) | 0.0174 (3) | |
H6 | 0.803909 | 0.470984 | 0.392239 | 0.021* | |
C7 | 0.39900 (15) | 0.8002 (2) | 0.57398 (13) | 0.0190 (3) | |
H7A | 0.417983 | 0.924214 | 0.598060 | 0.029* | |
H7B | 0.409833 | 0.717256 | 0.630717 | 0.029* | |
H7C | 0.313911 | 0.794339 | 0.535444 | 0.029* | |
B1 | 0.98218 (17) | 0.7522 (2) | 0.41861 (13) | 0.0143 (3) | |
N1 | 1.14551 (13) | 0.28718 (19) | 0.20638 (10) | 0.0142 (3) | |
H1B | 1.149 (2) | 0.368 (2) | 0.1603 (11) | 0.028 (6)* | |
H1C | 1.131 (2) | 0.1802 (13) | 0.1782 (14) | 0.026 (5)* | |
H1D | 1.2181 (10) | 0.287 (3) | 0.2475 (14) | 0.038 (7)* | |
O1 | 1.08772 (11) | 0.84897 (16) | 0.41822 (9) | 0.0179 (3) | |
H1A | 1.092 (2) | 0.9469 (15) | 0.4495 (14) | 0.034 (6)* | |
O2 | 0.89447 (11) | 0.82604 (16) | 0.46424 (9) | 0.0174 (2) | |
H2A | 0.8312 (12) | 0.766 (3) | 0.4643 (18) | 0.034 (6)* | |
O3 | 0.67631 (11) | 0.64619 (17) | 0.48249 (8) | 0.0202 (3) | |
O4 | 0.67689 (11) | 0.89182 (16) | 0.60384 (9) | 0.0202 (3) | |
O5 | 0.62808 (11) | 0.58524 (16) | 0.64640 (8) | 0.0191 (3) | |
O6 | 0.48264 (10) | 0.74674 (17) | 0.51004 (8) | 0.0185 (3) | |
S1 | 0.62503 (3) | 0.71551 (5) | 0.56395 (3) | 0.01183 (12) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0159 (7) | 0.0125 (7) | 0.0108 (6) | 0.0009 (6) | 0.0021 (5) | −0.0005 (6) |
C2 | 0.0150 (7) | 0.0116 (7) | 0.0127 (7) | −0.0015 (6) | 0.0032 (5) | 0.0004 (6) |
C3 | 0.0158 (7) | 0.0136 (7) | 0.0094 (6) | 0.0026 (6) | 0.0029 (5) | 0.0008 (6) |
C4 | 0.0228 (8) | 0.0125 (8) | 0.0170 (8) | −0.0018 (6) | 0.0053 (6) | −0.0051 (6) |
C5 | 0.0216 (8) | 0.0177 (8) | 0.0269 (9) | −0.0075 (7) | 0.0099 (7) | −0.0067 (7) |
C6 | 0.0176 (8) | 0.0173 (8) | 0.0191 (8) | −0.0010 (6) | 0.0078 (6) | −0.0044 (6) |
C7 | 0.0157 (8) | 0.0224 (9) | 0.0197 (8) | 0.0019 (6) | 0.0059 (6) | 0.0016 (7) |
B1 | 0.0174 (8) | 0.0120 (8) | 0.0134 (8) | 0.0006 (7) | 0.0037 (6) | −0.0004 (7) |
N1 | 0.0166 (7) | 0.0137 (7) | 0.0122 (6) | 0.0015 (5) | 0.0032 (5) | −0.0026 (5) |
O1 | 0.0199 (6) | 0.0125 (6) | 0.0234 (6) | −0.0033 (5) | 0.0090 (5) | −0.0074 (5) |
O2 | 0.0179 (6) | 0.0137 (6) | 0.0226 (6) | −0.0035 (5) | 0.0092 (5) | −0.0067 (5) |
O3 | 0.0203 (6) | 0.0254 (6) | 0.0176 (5) | −0.0027 (5) | 0.0098 (4) | −0.0072 (5) |
O4 | 0.0198 (6) | 0.0157 (6) | 0.0261 (6) | −0.0034 (5) | 0.0076 (5) | −0.0057 (5) |
O5 | 0.0222 (6) | 0.0168 (6) | 0.0196 (6) | 0.0031 (5) | 0.0075 (5) | 0.0073 (5) |
O6 | 0.0147 (6) | 0.0271 (6) | 0.0133 (5) | 0.0012 (5) | 0.0025 (4) | 0.0006 (5) |
S1 | 0.01295 (19) | 0.0115 (2) | 0.01144 (19) | −0.00018 (13) | 0.00369 (13) | 0.00016 (13) |
Geometric parameters (Å, º) top
C1—C2 | 1.400 (2) | C7—H7C | 0.9600 |
C1—C6 | 1.401 (2) | C7—O6 | 1.4524 (19) |
C1—B1 | 1.581 (2) | B1—O1 | 1.354 (2) |
C2—H2 | 0.9300 | B1—O2 | 1.367 (2) |
C2—C3 | 1.383 (2) | N1—H1B | 0.8601 (10) |
C3—C4 | 1.377 (2) | N1—H1C | 0.8601 (10) |
C3—N1 | 1.4716 (19) | N1—H1D | 0.8600 (10) |
C4—H4 | 0.9300 | O1—H1A | 0.8200 (10) |
C4—C5 | 1.390 (2) | O2—H2A | 0.8199 (11) |
C5—H5 | 0.9300 | O3—S1 | 1.4396 (11) |
C5—C6 | 1.390 (2) | O4—S1 | 1.4480 (12) |
C6—H6 | 0.9300 | O5—S1 | 1.4552 (11) |
C7—H7A | 0.9600 | O6—S1 | 1.5811 (11) |
C7—H7B | 0.9600 | | |
| | | |
C2—C1—C6 | 117.43 (14) | O6—C7—H7A | 109.5 |
C2—C1—B1 | 118.59 (14) | O6—C7—H7B | 109.5 |
C6—C1—B1 | 123.98 (14) | O6—C7—H7C | 109.5 |
C1—C2—H2 | 119.7 | O1—B1—C1 | 116.69 (14) |
C3—C2—C1 | 120.53 (14) | O1—B1—O2 | 119.53 (14) |
C3—C2—H2 | 119.7 | O2—B1—C1 | 123.77 (14) |
C2—C3—N1 | 118.60 (14) | C3—N1—H1B | 110.9 (14) |
C4—C3—C2 | 121.93 (14) | C3—N1—H1C | 111.2 (15) |
C4—C3—N1 | 119.46 (14) | C3—N1—H1D | 110.0 (16) |
C3—C4—H4 | 120.8 | H1B—N1—H1C | 108.6 (19) |
C3—C4—C5 | 118.36 (15) | H1B—N1—H1D | 106 (2) |
C5—C4—H4 | 120.8 | H1C—N1—H1D | 110 (2) |
C4—C5—H5 | 119.8 | B1—O1—H1A | 113.1 (16) |
C4—C5—C6 | 120.47 (15) | B1—O2—H2A | 118.6 (16) |
C6—C5—H5 | 119.8 | C7—O6—S1 | 117.11 (10) |
C1—C6—H6 | 119.4 | O3—S1—O4 | 113.74 (7) |
C5—C6—C1 | 121.29 (14) | O3—S1—O5 | 114.82 (7) |
C5—C6—H6 | 119.4 | O3—S1—O6 | 102.42 (6) |
H7A—C7—H7B | 109.5 | O4—S1—O5 | 110.18 (7) |
H7A—C7—H7C | 109.5 | O4—S1—O6 | 107.96 (7) |
H7B—C7—H7C | 109.5 | O5—S1—O6 | 106.98 (7) |
| | | |
C1—C2—C3—C4 | −0.8 (2) | C6—C1—B1—O1 | 177.38 (15) |
C1—C2—C3—N1 | 177.95 (13) | C6—C1—B1—O2 | −4.0 (2) |
C2—C1—C6—C5 | −0.1 (2) | C7—O6—S1—O3 | 174.01 (12) |
C2—C1—B1—O1 | −3.2 (2) | C7—O6—S1—O4 | −65.67 (13) |
C2—C1—B1—O2 | 175.46 (15) | C7—O6—S1—O5 | 52.90 (13) |
C2—C3—C4—C5 | 0.2 (2) | B1—C1—C2—C3 | −178.78 (13) |
C3—C4—C5—C6 | 0.4 (3) | B1—C1—C6—C5 | 179.39 (15) |
C4—C5—C6—C1 | −0.5 (3) | N1—C3—C4—C5 | −178.53 (15) |
C6—C1—C2—C3 | 0.7 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O6i | 0.86 (1) | 2.58 (1) | 2.959 (2) | 108 (1) |
N1—H1B···O4ii | 0.86 (1) | 1.95 (1) | 2.765 (2) | 158 (1) |
N1—H1C···O5iii | 0.86 (1) | 1.96 (1) | 2.804 (2) | 165 (1) |
N1—H1D···O4iv | 0.86 (1) | 2.45 (1) | 3.126 (2) | 136 (1) |
N1—H1D···O5iv | 0.86 (1) | 2.16 (1) | 2.952 (2) | 154 (1) |
O1—H1A···O2v | 0.82 (1) | 2.00 (1) | 2.818 (2) | 176 (1) |
O2—H2A···O3 | 0.82 (2) | 1.97 (1) | 2.785 (2) | 171 (2) |
C2—H2···O1 | 0.93 | 2.51 | 2.860 (2) | 103 |
C6—H6···O3 | 0.93 | 2.42 | 3.316 (2) | 162 |
C7—H7B···O5 | 0.96 | 2.54 | 2.925 (2) | 104 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x+1/2, −y+3/2, z−1/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+2, −y+1, −z+1; (v) −x+2, −y+2, −z+1. |
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