| Literature DB >> 22904959 |
Garima Sharma, S Vasanth Kumar, Habibah A Wahab, Mohd Mustaqim Rosli, Hoong-Kun Fun.
Abstract
In the title compound, C(23)H(20)N(2)O(3)·CH(3)OH, the hexa-hydro-1H-benzo[f]isoindole and indoline rings are planar, with maximum deviations of 0.092 (1) and -0.095 (1) Å, respectively. The dihedral angle between these two rings is 88.03 (4)°. An O-H⋯N inter-action links the main mol-ecule and the methanol solvent mol-ecule. An intra-molecular C-H⋯O inter-action forms an S(6) ring motif. In the crystal, the mol-ecules form two-dimensional layers parallel to the bc plane through N-H⋯O and C-H⋯O inter-actions.Entities:
Year: 2012 PMID: 22904959 PMCID: PMC3414972 DOI: 10.1107/S1600536812032643
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C23H20N2O3·CH4O | |
| Monoclinic, | Mo |
| Hall symbol: -P 2ybc | Cell parameters from 7290 reflections |
| θ = 2.6–30.1° | |
| µ = 0.09 mm−1 | |
| β = 111.246 (1)° | Block, brown |
| 0.32 × 0.20 × 0.11 mm | |
| Bruker SMART APEXII CCD area-detector diffractometer | 5871 independent reflections |
| Radiation source: fine-focus sealed tube | 4460 reflections with |
| Graphite monochromator | |
| φ and ω scans | θmax = 30.1°, θmin = 2.0° |
| Absorption correction: multi-scan ( | |
| 23197 measured reflections |
| Refinement on | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| Hydrogen site location: inferred from neighbouring sites | |
| H atoms treated by a mixture of independent and constrained refinement | |
| 5871 reflections | (Δ/σ)max < 0.001 |
| 286 parameters | Δρmax = 0.63 e Å−3 |
| 0 restraints | Δρmin = −0.46 e Å−3 |
| Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
| 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 |
| O1 | 0.09694 (11) | 0.90322 (10) | 0.51378 (7) | 0.0300 (3) | |
| O2 | 0.56629 (10) | 1.07980 (8) | 0.70838 (7) | 0.0186 (2) | |
| O3 | 0.35764 (11) | 1.07705 (9) | 0.83896 (7) | 0.0235 (2) | |
| N1 | 0.33921 (12) | 0.82889 (10) | 0.78597 (8) | 0.0160 (2) | |
| N2 | 0.56151 (12) | 1.00095 (10) | 0.91874 (8) | 0.0187 (3) | |
| C1 | 0.40186 (14) | 1.06328 (11) | 0.56677 (9) | 0.0159 (3) | |
| C2 | 0.46388 (15) | 1.13840 (12) | 0.52980 (9) | 0.0187 (3) | |
| H2A | 0.5469 | 1.1698 | 0.5640 | 0.022* | |
| C3 | 0.40491 (16) | 1.16770 (12) | 0.44316 (10) | 0.0219 (3) | |
| H3A | 0.4469 | 1.2198 | 0.4183 | 0.026* | |
| C4 | 0.28436 (16) | 1.12071 (13) | 0.39287 (10) | 0.0234 (3) | |
| H4A | 0.2450 | 1.1399 | 0.3334 | 0.028* | |
| C5 | 0.22110 (16) | 1.04605 (13) | 0.42882 (9) | 0.0218 (3) | |
| H5A | 0.1385 | 1.0146 | 0.3940 | 0.026* | |
| C6 | 0.27860 (14) | 1.01691 (11) | 0.51630 (9) | 0.0179 (3) | |
| C7 | 0.20717 (15) | 0.93985 (12) | 0.55492 (9) | 0.0198 (3) | |
| C8 | 0.27704 (14) | 0.90981 (12) | 0.64722 (9) | 0.0172 (3) | |
| C9 | 0.22425 (14) | 0.83749 (12) | 0.70212 (9) | 0.0170 (3) | |
| H9A | 0.1503 | 0.8777 | 0.7122 | 0.020* | |
| C10 | 0.44298 (13) | 0.91165 (11) | 0.78621 (9) | 0.0146 (3) | |
| C11 | 0.39672 (14) | 0.95085 (11) | 0.69362 (9) | 0.0155 (3) | |
| C12 | 0.46506 (14) | 1.03460 (11) | 0.66010 (9) | 0.0148 (3) | |
| C13 | 0.17636 (14) | 0.72159 (12) | 0.66517 (9) | 0.0177 (3) | |
| H13A | 0.2508 | 0.6815 | 0.6570 | 0.021* | |
| H13B | 0.1061 | 0.7307 | 0.6074 | 0.021* | |
| C14 | 0.12248 (14) | 0.64910 (12) | 0.72118 (10) | 0.0184 (3) | |
| H14A | 0.1887 | 0.6484 | 0.7817 | 0.022* | |
| C15 | −0.00825 (16) | 0.69353 (14) | 0.72296 (12) | 0.0297 (4) | |
| H15A | −0.0398 | 0.6443 | 0.7587 | 0.044* | |
| H15B | −0.0738 | 0.6957 | 0.6639 | 0.044* | |
| H15C | 0.0048 | 0.7691 | 0.7475 | 0.044* | |
| C16 | 0.10456 (16) | 0.52942 (13) | 0.68612 (11) | 0.0238 (3) | |
| H16A | 0.0629 | 0.4839 | 0.7183 | 0.036* | |
| H16B | 0.1911 | 0.4977 | 0.6929 | 0.036* | |
| H16C | 0.0482 | 0.5300 | 0.6246 | 0.036* | |
| C17 | 0.44567 (14) | 1.00939 (12) | 0.84967 (9) | 0.0170 (3) | |
| C18 | 0.58027 (13) | 0.86393 (11) | 0.82701 (9) | 0.0151 (3) | |
| C19 | 0.64232 (14) | 0.77902 (12) | 0.79995 (9) | 0.0182 (3) | |
| H19A | 0.6009 | 0.7448 | 0.7450 | 0.022* | |
| C20 | 0.76752 (15) | 0.74465 (13) | 0.85537 (10) | 0.0223 (3) | |
| H20A | 0.8126 | 0.6872 | 0.8376 | 0.027* | |
| C21 | 0.82649 (15) | 0.79390 (14) | 0.93626 (11) | 0.0252 (3) | |
| H21A | 0.9106 | 0.7680 | 0.9737 | 0.030* | |
| C22 | 0.76496 (15) | 0.88039 (13) | 0.96365 (10) | 0.0232 (3) | |
| H22A | 0.8056 | 0.9140 | 1.0189 | 0.028* | |
| C23 | 0.64231 (14) | 0.91542 (12) | 0.90724 (9) | 0.0172 (3) | |
| O4 | 0.31230 (12) | 0.84323 (11) | 0.94796 (8) | 0.0309 (3) | |
| C24 | 0.1798 (2) | 0.8342 (2) | 0.93687 (13) | 0.0425 (5) | |
| H24A | 0.1507 | 0.7567 | 0.9226 | 0.064* | |
| H24B | 0.1274 | 0.8835 | 0.8896 | 0.064* | |
| H24C | 0.1676 | 0.8561 | 0.9905 | 0.064* | |
| H1N1 | 0.3759 (17) | 0.7609 (16) | 0.7870 (11) | 0.021 (4)* | |
| H1N2 | 0.587 (2) | 1.0493 (17) | 0.9621 (13) | 0.031 (5)* | |
| H1O4 | 0.317 (2) | 0.842 (2) | 0.8928 (17) | 0.056 (7)* |
| O1 | 0.0248 (6) | 0.0283 (6) | 0.0245 (6) | −0.0059 (5) | −0.0059 (5) | 0.0056 (5) |
| O2 | 0.0176 (5) | 0.0176 (5) | 0.0178 (5) | −0.0019 (4) | 0.0029 (4) | −0.0001 (4) |
| O3 | 0.0241 (6) | 0.0198 (5) | 0.0255 (6) | 0.0038 (4) | 0.0076 (5) | −0.0032 (4) |
| N1 | 0.0158 (6) | 0.0149 (6) | 0.0149 (5) | −0.0019 (4) | 0.0027 (5) | −0.0005 (4) |
| N2 | 0.0202 (6) | 0.0187 (6) | 0.0149 (6) | −0.0024 (5) | 0.0036 (5) | −0.0056 (5) |
| C1 | 0.0193 (7) | 0.0131 (6) | 0.0137 (6) | 0.0038 (5) | 0.0042 (5) | −0.0008 (5) |
| C2 | 0.0237 (7) | 0.0154 (7) | 0.0175 (7) | 0.0014 (5) | 0.0078 (6) | −0.0017 (5) |
| C3 | 0.0307 (8) | 0.0182 (7) | 0.0188 (7) | 0.0041 (6) | 0.0114 (6) | 0.0035 (5) |
| C4 | 0.0309 (8) | 0.0223 (7) | 0.0152 (7) | 0.0071 (6) | 0.0060 (6) | 0.0032 (5) |
| C5 | 0.0246 (7) | 0.0191 (7) | 0.0163 (7) | 0.0037 (6) | 0.0009 (6) | −0.0003 (5) |
| C6 | 0.0212 (7) | 0.0138 (6) | 0.0155 (6) | 0.0036 (5) | 0.0028 (5) | −0.0003 (5) |
| C7 | 0.0207 (7) | 0.0150 (6) | 0.0176 (7) | 0.0002 (5) | −0.0004 (6) | 0.0002 (5) |
| C8 | 0.0180 (7) | 0.0141 (6) | 0.0157 (6) | 0.0005 (5) | 0.0018 (5) | 0.0005 (5) |
| C9 | 0.0148 (6) | 0.0164 (6) | 0.0165 (6) | −0.0011 (5) | 0.0017 (5) | −0.0002 (5) |
| C10 | 0.0151 (6) | 0.0139 (6) | 0.0126 (6) | −0.0014 (5) | 0.0024 (5) | −0.0011 (5) |
| C11 | 0.0176 (6) | 0.0136 (6) | 0.0130 (6) | 0.0012 (5) | 0.0026 (5) | 0.0000 (5) |
| C12 | 0.0166 (6) | 0.0118 (6) | 0.0145 (6) | 0.0020 (5) | 0.0040 (5) | −0.0006 (5) |
| C13 | 0.0155 (6) | 0.0171 (7) | 0.0168 (6) | −0.0019 (5) | 0.0013 (5) | −0.0012 (5) |
| C14 | 0.0161 (6) | 0.0182 (7) | 0.0189 (7) | −0.0016 (5) | 0.0039 (5) | −0.0015 (5) |
| C15 | 0.0235 (8) | 0.0269 (8) | 0.0410 (10) | −0.0014 (6) | 0.0146 (7) | −0.0059 (7) |
| C16 | 0.0257 (8) | 0.0176 (7) | 0.0269 (8) | −0.0032 (6) | 0.0080 (6) | −0.0015 (6) |
| C17 | 0.0194 (7) | 0.0145 (6) | 0.0172 (6) | −0.0024 (5) | 0.0066 (6) | −0.0010 (5) |
| C18 | 0.0156 (6) | 0.0142 (6) | 0.0144 (6) | −0.0005 (5) | 0.0043 (5) | 0.0025 (5) |
| C19 | 0.0203 (7) | 0.0163 (7) | 0.0190 (7) | −0.0016 (5) | 0.0085 (6) | 0.0020 (5) |
| C20 | 0.0215 (7) | 0.0187 (7) | 0.0298 (8) | 0.0030 (6) | 0.0130 (6) | 0.0069 (6) |
| C21 | 0.0166 (7) | 0.0272 (8) | 0.0285 (8) | 0.0015 (6) | 0.0043 (6) | 0.0110 (6) |
| C22 | 0.0198 (7) | 0.0275 (8) | 0.0172 (7) | −0.0036 (6) | 0.0004 (6) | 0.0033 (6) |
| C23 | 0.0180 (7) | 0.0174 (7) | 0.0152 (6) | −0.0026 (5) | 0.0048 (5) | 0.0019 (5) |
| O4 | 0.0261 (6) | 0.0436 (7) | 0.0229 (6) | −0.0067 (5) | 0.0087 (5) | −0.0121 (5) |
| C24 | 0.0354 (10) | 0.0640 (14) | 0.0313 (10) | −0.0139 (9) | 0.0161 (8) | −0.0126 (9) |
| O1—C7 | 1.2231 (18) | C11—C12 | 1.470 (2) |
| O2—C12 | 1.2254 (17) | C13—C14 | 1.532 (2) |
| O3—C17 | 1.2147 (18) | C13—H13A | 0.9900 |
| N1—C9 | 1.4969 (18) | C13—H13B | 0.9900 |
| N1—C10 | 1.4979 (18) | C14—C15 | 1.525 (2) |
| N1—H1N1 | 0.902 (19) | C14—C16 | 1.531 (2) |
| N2—C17 | 1.3627 (19) | C14—H14A | 1.0000 |
| N2—C23 | 1.4043 (19) | C15—H15A | 0.9800 |
| N2—H1N2 | 0.88 (2) | C15—H15B | 0.9800 |
| C1—C2 | 1.391 (2) | C15—H15C | 0.9800 |
| C1—C6 | 1.409 (2) | C16—H16A | 0.9800 |
| C1—C12 | 1.4870 (19) | C16—H16B | 0.9800 |
| C2—C3 | 1.388 (2) | C16—H16C | 0.9800 |
| C2—H2A | 0.9500 | C18—C19 | 1.380 (2) |
| C3—C4 | 1.390 (2) | C18—C23 | 1.3969 (19) |
| C3—H3A | 0.9500 | C19—C20 | 1.398 (2) |
| C4—C5 | 1.386 (2) | C19—H19A | 0.9500 |
| C4—H4A | 0.9500 | C20—C21 | 1.390 (2) |
| C5—C6 | 1.3989 (19) | C20—H20A | 0.9500 |
| C5—H5A | 0.9500 | C21—C22 | 1.393 (2) |
| C6—C7 | 1.490 (2) | C21—H21A | 0.9500 |
| C7—C8 | 1.484 (2) | C22—C23 | 1.385 (2) |
| C8—C11 | 1.3395 (19) | C22—H22A | 0.9500 |
| C8—C9 | 1.510 (2) | O4—C24 | 1.386 (2) |
| C9—C13 | 1.528 (2) | O4—H1O4 | 0.93 (3) |
| C9—H9A | 1.0000 | C24—H24A | 0.9800 |
| C10—C11 | 1.5059 (19) | C24—H24B | 0.9800 |
| C10—C18 | 1.5072 (19) | C24—H24C | 0.9800 |
| C10—C17 | 1.5656 (19) | ||
| C9—N1—C10 | 109.25 (11) | C14—C13—H13A | 108.6 |
| C9—N1—H1N1 | 107.0 (11) | C9—C13—H13B | 108.6 |
| C10—N1—H1N1 | 105.6 (12) | C14—C13—H13B | 108.6 |
| C17—N2—C23 | 111.78 (12) | H13A—C13—H13B | 107.5 |
| C17—N2—H1N2 | 123.9 (13) | C15—C14—C16 | 110.01 (13) |
| C23—N2—H1N2 | 123.9 (13) | C15—C14—C13 | 112.09 (13) |
| C2—C1—C6 | 119.98 (13) | C16—C14—C13 | 108.85 (12) |
| C2—C1—C12 | 119.52 (13) | C15—C14—H14A | 108.6 |
| C6—C1—C12 | 120.48 (13) | C16—C14—H14A | 108.6 |
| C3—C2—C1 | 120.22 (14) | C13—C14—H14A | 108.6 |
| C3—C2—H2A | 119.9 | C14—C15—H15A | 109.5 |
| C1—C2—H2A | 119.9 | C14—C15—H15B | 109.5 |
| C2—C3—C4 | 119.93 (15) | H15A—C15—H15B | 109.5 |
| C2—C3—H3A | 120.0 | C14—C15—H15C | 109.5 |
| C4—C3—H3A | 120.0 | H15A—C15—H15C | 109.5 |
| C5—C4—C3 | 120.53 (14) | H15B—C15—H15C | 109.5 |
| C5—C4—H4A | 119.7 | C14—C16—H16A | 109.5 |
| C3—C4—H4A | 119.7 | C14—C16—H16B | 109.5 |
| C4—C5—C6 | 120.12 (14) | H16A—C16—H16B | 109.5 |
| C4—C5—H5A | 119.9 | C14—C16—H16C | 109.5 |
| C6—C5—H5A | 119.9 | H16A—C16—H16C | 109.5 |
| C5—C6—C1 | 119.20 (14) | H16B—C16—H16C | 109.5 |
| C5—C6—C7 | 119.56 (13) | O3—C17—N2 | 127.52 (13) |
| C1—C6—C7 | 121.22 (12) | O3—C17—C10 | 125.24 (13) |
| O1—C7—C8 | 121.25 (14) | N2—C17—C10 | 107.21 (12) |
| O1—C7—C6 | 122.55 (13) | C19—C18—C23 | 120.68 (13) |
| C8—C7—C6 | 116.20 (12) | C19—C18—C10 | 130.70 (13) |
| C11—C8—C7 | 121.98 (14) | C23—C18—C10 | 108.48 (12) |
| C11—C8—C9 | 111.37 (12) | C18—C19—C20 | 118.38 (14) |
| C7—C8—C9 | 126.57 (12) | C18—C19—H19A | 120.8 |
| N1—C9—C8 | 103.19 (11) | C20—C19—H19A | 120.8 |
| N1—C9—C13 | 110.95 (11) | C21—C20—C19 | 120.48 (15) |
| C8—C9—C13 | 115.22 (12) | C21—C20—H20A | 119.8 |
| N1—C9—H9A | 109.1 | C19—C20—H20A | 119.8 |
| C8—C9—H9A | 109.1 | C20—C21—C22 | 121.43 (14) |
| C13—C9—H9A | 109.1 | C20—C21—H21A | 119.3 |
| N1—C10—C11 | 103.32 (10) | C22—C21—H21A | 119.3 |
| N1—C10—C18 | 111.75 (11) | C23—C22—C21 | 117.46 (14) |
| C11—C10—C18 | 119.03 (12) | C23—C22—H22A | 121.3 |
| N1—C10—C17 | 109.04 (11) | C21—C22—H22A | 121.3 |
| C11—C10—C17 | 111.72 (11) | C22—C23—C18 | 121.51 (14) |
| C18—C10—C17 | 101.93 (11) | C22—C23—N2 | 128.54 (14) |
| C8—C11—C12 | 123.34 (12) | C18—C23—N2 | 109.95 (12) |
| C8—C11—C10 | 111.50 (13) | C24—O4—H1O4 | 106.8 (15) |
| C12—C11—C10 | 124.73 (12) | O4—C24—H24A | 109.5 |
| O2—C12—C11 | 120.62 (12) | O4—C24—H24B | 109.5 |
| O2—C12—C1 | 122.93 (13) | H24A—C24—H24B | 109.5 |
| C11—C12—C1 | 116.40 (12) | O4—C24—H24C | 109.5 |
| C9—C13—C14 | 114.79 (12) | H24A—C24—H24C | 109.5 |
| C9—C13—H13A | 108.6 | H24B—C24—H24C | 109.5 |
| C6—C1—C2—C3 | −0.2 (2) | C10—C11—C12—O2 | −1.2 (2) |
| C12—C1—C2—C3 | −178.75 (13) | C8—C11—C12—C1 | −7.1 (2) |
| C1—C2—C3—C4 | −0.9 (2) | C10—C11—C12—C1 | −178.98 (12) |
| C2—C3—C4—C5 | 1.1 (2) | C2—C1—C12—O2 | 5.0 (2) |
| C3—C4—C5—C6 | −0.3 (2) | C6—C1—C12—O2 | −173.59 (13) |
| C4—C5—C6—C1 | −0.8 (2) | C2—C1—C12—C11 | −177.33 (13) |
| C4—C5—C6—C7 | 177.73 (14) | C6—C1—C12—C11 | 4.10 (19) |
| C2—C1—C6—C5 | 1.0 (2) | N1—C9—C13—C14 | 63.48 (16) |
| C12—C1—C6—C5 | 179.55 (13) | C8—C9—C13—C14 | −179.76 (12) |
| C2—C1—C6—C7 | −177.48 (13) | C9—C13—C14—C15 | 69.24 (16) |
| C12—C1—C6—C7 | 1.1 (2) | C9—C13—C14—C16 | −168.83 (12) |
| C5—C6—C7—O1 | −2.5 (2) | C23—N2—C17—O3 | −177.45 (15) |
| C1—C6—C7—O1 | 175.95 (15) | C23—N2—C17—C10 | 4.59 (16) |
| C5—C6—C7—C8 | 177.82 (13) | N1—C10—C17—O3 | −67.24 (18) |
| C1—C6—C7—C8 | −3.7 (2) | C11—C10—C17—O3 | 46.32 (19) |
| O1—C7—C8—C11 | −178.74 (15) | C18—C10—C17—O3 | 174.49 (14) |
| C6—C7—C8—C11 | 0.9 (2) | N1—C10—C17—N2 | 110.78 (13) |
| O1—C7—C8—C9 | −2.3 (2) | C11—C10—C17—N2 | −135.65 (13) |
| C6—C7—C8—C9 | 177.34 (13) | C18—C10—C17—N2 | −7.49 (14) |
| C10—N1—C9—C8 | 11.53 (14) | N1—C10—C18—C19 | 67.08 (19) |
| C10—N1—C9—C13 | 135.47 (12) | C11—C10—C18—C19 | −53.3 (2) |
| C11—C8—C9—N1 | −7.48 (16) | C17—C10—C18—C19 | −176.60 (14) |
| C7—C8—C9—N1 | 175.79 (13) | N1—C10—C18—C23 | −108.46 (13) |
| C11—C8—C9—C13 | −128.56 (13) | C11—C10—C18—C23 | 131.21 (13) |
| C7—C8—C9—C13 | 54.71 (19) | C17—C10—C18—C23 | 7.86 (14) |
| C9—N1—C10—C11 | −11.27 (14) | C23—C18—C19—C20 | 1.1 (2) |
| C9—N1—C10—C18 | −140.42 (12) | C10—C18—C19—C20 | −173.99 (14) |
| C9—N1—C10—C17 | 107.68 (12) | C18—C19—C20—C21 | 1.1 (2) |
| C7—C8—C11—C12 | 4.6 (2) | C19—C20—C21—C22 | −1.7 (2) |
| C9—C8—C11—C12 | −172.30 (13) | C20—C21—C22—C23 | 0.2 (2) |
| C7—C8—C11—C10 | 177.44 (13) | C21—C22—C23—C18 | 2.0 (2) |
| C9—C8—C11—C10 | 0.53 (17) | C21—C22—C23—N2 | −179.06 (14) |
| N1—C10—C11—C8 | 6.65 (15) | C19—C18—C23—C22 | −2.7 (2) |
| C18—C10—C11—C8 | 131.18 (13) | C10—C18—C23—C22 | 173.37 (13) |
| C17—C10—C11—C8 | −110.43 (14) | C19—C18—C23—N2 | 178.20 (13) |
| N1—C10—C11—C12 | 179.36 (12) | C10—C18—C23—N2 | −5.73 (16) |
| C18—C10—C11—C12 | −56.11 (18) | C17—N2—C23—C22 | −178.43 (15) |
| C17—C10—C11—C12 | 62.28 (18) | C17—N2—C23—C18 | 0.59 (17) |
| C8—C11—C12—O2 | 170.65 (14) |
| H··· | ||||
| N1—H1 | 0.903 (19) | 2.249 (19) | 3.1410 (16) | 169.7 (17) |
| N2—H1 | 0.89 (2) | 1.97 (2) | 2.8346 (18) | 165 (2) |
| O4—H1 | 0.93 (3) | 1.88 (3) | 2.8085 (18) | 174 (2) |
| C13—H13 | 0.99 | 2.56 | 3.1919 (18) | 121 |
| C19—H19 | 0.95 | 2.57 | 3.3368 (18) | 138 |
Hydrogen-bond geometry (Å, °)
|
|
| H⋯ |
|
|
|---|---|---|---|---|
| N1—H1N1⋯O2i | 0.903 (19) | 2.249 (19) | 3.1410 (16) | 169.7 (17) |
| N2—H1N2⋯O4ii | 0.89 (2) | 1.97 (2) | 2.8346 (18) | 165 (2) |
| O4—H1O4⋯N1 | 0.93 (3) | 1.88 (3) | 2.8085 (18) | 174 (2) |
| C13—H13 | 0.99 | 2.56 | 3.1919 (18) | 121 |
| C19—H19 | 0.95 | 2.57 | 3.3368 (18) | 138 |
Symmetry codes: (i) ; (ii) .