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Cocrystals of 2,7-dihydroxynaphthalene (DHN, or naphthalene-2,7-diol) with isoniazid (pyridine-4-carbohydrazide) (INH), denoted DHN–INH [C10H8O2·C6H7N3O, (I)], and piracetam [2-(2-oxopyrrolidin-1-yl)acetamide] (PIR), denoted DHN–PIR [C10H8O2·C6H10N2O2, (II)], were obtained by the solvent-assisted grinding method and characterized by IR spectroscopy, powder X-ray diffraction and single-crystal X-ray diffraction. Cocrystal (I) crystallized in the triclinic space group P
and showed a 2:2 stoichiometry. DHN and INH molecules are connected by O—H
N(pyridine) and O—HN(hydrazide) hydrogen bonds. Cocrystal (II) crystallized in the space group Pca21 with a 1:1 stoichiometry. DHN and PIR molecules are connected by O—HO=C hydrogen bonds. The supramolecular architecture of cocrystal (I) showed interlinked supramolecular tapes; meanwhile, in cocrystal (II), interlinked supramolecular sheets were observed.
and showed a 2:2 stoichiometry. DHN and INH molecules are connected by O—HN(pyridine) and O—HN(hydrazide) hydrogen bonds. Cocrystal (II) crystallized in the space group Pca21 with a 1:1 stoichiometry. DHN and PIR molecules are connected by O—HO=C hydrogen bonds. The supramolecular architecture of cocrystal (I) showed interlinked supramolecular tapes; meanwhile, in cocrystal (II), interlinked supramolecular sheets were observed.Keywords: cocrystal; piracetam; isoniazid; 2,7-dihydroxynaphthalene; crystal structure; IR spectroscopy; API; active pharmaceutical ingredient; solvent-assisted grinding.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622003734/ky3216sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S2053229622003734/ky3216Isup2.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229622003734/ky3216IIsup3.hkl |
 | Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622003734/ky3216Isup4.cml |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622003734/ky3216IIsup5.cml |
CCDC references: 2164548; 2164549
Computing details top
For both structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2020) and WinGX (Farrugia, 2012).
Naphthalene-2,7-diol; pyridine-4-carbohydrazide (I) top
Crystal data top
| C10H8O2·C6H7N3O | Z = 4 |
| Mr = 297.31 | F(000) = 624 |
| Triclinic, P1 | Dx = 1.413 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.0118 (8) Å | Cell parameters from 4934 reflections |
| b = 11.8026 (8) Å | θ = 3.5–29.3° |
| c = 13.6496 (8) Å | µ = 0.1 mm−1 |
| α = 65.234 (6)° | T = 130 K |
| β = 73.354 (6)° | Block, colourless |
| γ = 78.437 (6)° | 0.56 × 0.44 × 0.38 mm |
| V = 1397.18 (19) Å3 |
Data collection top
| Agilent Xcalibur Atlas Gemini diffractometer | 6386 independent reflections |
| Graphite monochromator | 5427 reflections with I > 2σ(I) |
| Detector resolution: 10.4685 pixels mm-1 | Rint = 0.019 |
| ω scans | θmax = 29.3°, θmin = 3.5° |
| Absorption correction: analytical [CrysAlis PRO (Agilent, 2013), based on expressions derived by Clark & Reid (1995)] | h = −13→12 |
| Tmin = 0.957, Tmax = 0.969 | k = −15→15 |
| 10805 measured reflections | l = −18→18 |
Refinement top
| Refinement on F2 | Hydrogen site location: mixed |
| Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
| R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0673P)2 + 0.3595P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.114 | (Δ/σ)max = 0.001 |
| S = 1.00 | Δρmax = 0.38 e Å−3 |
| 6386 reflections | Δρmin = −0.21 e Å−3 |
| 428 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 10 restraints | Extinction coefficient: 0.053 (3) |
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 | 0.85909 (12) | 0.65337 (11) | 0.34248 (10) | 0.0158 (2) | |
| H1 | 0.843007 | 0.581924 | 0.409855 | 0.019* | |
| C2 | 0.79430 (12) | 0.67174 (11) | 0.26016 (10) | 0.0167 (2) | |
| C3 | 0.82044 (13) | 0.77631 (12) | 0.15795 (10) | 0.0190 (3) | |
| H3 | 0.7763 | 0.788104 | 0.100908 | 0.023* | |
| C4 | 0.90878 (13) | 0.85967 (11) | 0.14172 (10) | 0.0179 (2) | |
| H4 | 0.926344 | 0.928679 | 0.072629 | 0.021* | |
| C5 | 1.05961 (13) | 0.93609 (11) | 0.21314 (10) | 0.0183 (2) | |
| H5 | 1.078825 | 1.005451 | 0.144484 | 0.022* | |
| C6 | 1.11405 (13) | 0.92533 (11) | 0.29809 (11) | 0.0191 (3) | |
| H6 | 1.169353 | 0.987362 | 0.288737 | 0.023* | |
| C7 | 1.08761 (12) | 0.82142 (11) | 0.39991 (10) | 0.0167 (2) | |
| C8 | 1.01197 (12) | 0.72894 (11) | 0.41290 (10) | 0.0165 (2) | |
| H8 | 1.001155 | 0.656532 | 0.479804 | 0.02* | |
| C9 | 0.94993 (12) | 0.74038 (11) | 0.32763 (10) | 0.0151 (2) | |
| C10 | 0.97527 (12) | 0.84606 (11) | 0.22542 (10) | 0.0159 (2) | |
| C11 | 0.55038 (12) | 0.09760 (11) | 0.10670 (9) | 0.0147 (2) | |
| H11 | 0.605204 | 0.020569 | 0.111595 | 0.018* | |
| C12 | 0.41890 (12) | 0.11823 (11) | 0.08631 (9) | 0.0154 (2) | |
| C13 | 0.33621 (13) | 0.23297 (11) | 0.07820 (10) | 0.0183 (2) | |
| H13 | 0.245625 | 0.24648 | 0.063985 | 0.022* | |
| C14 | 0.38663 (13) | 0.32406 (11) | 0.09081 (10) | 0.0183 (2) | |
| H14 | 0.330489 | 0.400739 | 0.084937 | 0.022* | |
| C15 | 0.57511 (13) | 0.39783 (11) | 0.12898 (10) | 0.0187 (3) | |
| H15 | 0.519788 | 0.474488 | 0.124787 | 0.022* | |
| C16 | 0.70477 (14) | 0.37836 (11) | 0.15076 (10) | 0.0199 (3) | |
| H16 | 0.738247 | 0.440264 | 0.162726 | 0.024* | |
| C17 | 0.78886 (13) | 0.26494 (12) | 0.15533 (10) | 0.0190 (3) | |
| C18 | 0.73928 (13) | 0.17370 (11) | 0.14105 (10) | 0.0169 (2) | |
| H18 | 0.796396 | 0.097882 | 0.145067 | 0.02* | |
| C19 | 0.60425 (12) | 0.19109 (11) | 0.12041 (9) | 0.0146 (2) | |
| C20 | 0.52118 (13) | 0.30648 (11) | 0.11251 (9) | 0.0158 (2) | |
| C23 | 0.49553 (12) | 0.22136 (11) | 0.53932 (10) | 0.0150 (2) | |
| C24 | 0.40633 (12) | 0.15454 (10) | 0.51307 (10) | 0.0144 (2) | |
| C25 | 0.31588 (12) | 0.07336 (11) | 0.60044 (10) | 0.0167 (2) | |
| H25 | 0.306254 | 0.065277 | 0.67431 | 0.02* | |
| C26 | 0.24003 (12) | 0.00445 (11) | 0.57819 (10) | 0.0180 (2) | |
| H26 | 0.177026 | −0.049511 | 0.638212 | 0.022* | |
| C28 | 0.33882 (13) | 0.08871 (12) | 0.39223 (10) | 0.0198 (3) | |
| H28 | 0.347465 | 0.093993 | 0.319326 | 0.024* | |
| C29 | 0.41741 (13) | 0.16252 (11) | 0.40646 (10) | 0.0182 (2) | |
| H29 | 0.477633 | 0.21746 | 0.344672 | 0.022* | |
| C33 | 0.68566 (12) | 0.39852 (11) | 0.74939 (10) | 0.0143 (2) | |
| C34 | 0.78844 (12) | 0.45609 (11) | 0.77191 (10) | 0.0145 (2) | |
| C35 | 0.82451 (13) | 0.57473 (12) | 0.69621 (10) | 0.0188 (3) | |
| H35 | 0.786723 | 0.615468 | 0.632185 | 0.023* | |
| C36 | 0.91612 (13) | 0.63267 (12) | 0.71534 (11) | 0.0216 (3) | |
| H36 | 0.939712 | 0.713849 | 0.663317 | 0.026* | |
| C38 | 0.93879 (13) | 0.46494 (12) | 0.87561 (11) | 0.0196 (3) | |
| H38 | 0.979353 | 0.425903 | 0.93827 | 0.024* | |
| C39 | 0.84779 (12) | 0.40032 (11) | 0.86367 (10) | 0.0167 (2) | |
| H39 | 0.826115 | 0.319262 | 0.917141 | 0.02* | |
| N21 | 0.63005 (12) | 0.39774 (10) | 0.47160 (10) | 0.0199 (2) | |
| H21D | 0.7091 (15) | 0.3447 (14) | 0.4822 (13) | 0.024* | |
| H21E | 0.5911 (16) | 0.4123 (14) | 0.5343 (12) | 0.024* | |
| N22 | 0.53751 (11) | 0.33089 (10) | 0.45870 (9) | 0.0196 (2) | |
| H22D | 0.4915 (16) | 0.3746 (14) | 0.4064 (12) | 0.023* | |
| N27 | 0.25129 (11) | 0.01028 (10) | 0.47587 (9) | 0.0185 (2) | |
| N31 | 0.55710 (12) | 0.21912 (10) | 0.81158 (9) | 0.0190 (2) | |
| H31D | 0.4730 (14) | 0.2655 (13) | 0.8127 (13) | 0.023* | |
| H31E | 0.5864 (16) | 0.2163 (14) | 0.7437 (11) | 0.023* | |
| N32 | 0.65133 (11) | 0.28479 (10) | 0.82285 (9) | 0.0186 (2) | |
| H32D | 0.6872 (16) | 0.2430 (14) | 0.8806 (12) | 0.022* | |
| N37 | 0.97298 (11) | 0.57959 (10) | 0.80373 (9) | 0.0210 (2) | |
| O2 | 0.70331 (10) | 0.59490 (9) | 0.26843 (8) | 0.0215 (2) | |
| H2D | 0.6872 (18) | 0.5362 (15) | 0.3353 (12) | 0.032* | |
| O7 | 1.13672 (9) | 0.81026 (8) | 0.48735 (7) | 0.0203 (2) | |
| H7D | 1.1746 (17) | 0.8793 (14) | 0.4750 (14) | 0.03* | |
| O12 | 0.36090 (9) | 0.03287 (8) | 0.07237 (7) | 0.01899 (19) | |
| H12D | 0.4074 (17) | −0.0412 (13) | 0.0987 (14) | 0.028* | |
| O17 | 0.92001 (10) | 0.24327 (9) | 0.17278 (9) | 0.0274 (2) | |
| H17D | 0.944 (2) | 0.3067 (15) | 0.1791 (16) | 0.041* | |
| O23 | 0.53165 (10) | 0.17543 (8) | 0.62746 (7) | 0.0214 (2) | |
| O33 | 0.63473 (10) | 0.45498 (8) | 0.66773 (8) | 0.0247 (2) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0155 (5) | 0.0139 (5) | 0.0169 (6) | −0.0026 (4) | −0.0035 (4) | −0.0045 (5) |
| C2 | 0.0150 (5) | 0.0163 (6) | 0.0208 (6) | −0.0030 (4) | −0.0035 (4) | −0.0087 (5) |
| C3 | 0.0195 (6) | 0.0217 (6) | 0.0175 (6) | −0.0018 (5) | −0.0063 (5) | −0.0079 (5) |
| C4 | 0.0193 (6) | 0.0172 (6) | 0.0142 (6) | −0.0026 (4) | −0.0026 (4) | −0.0037 (5) |
| C5 | 0.0171 (6) | 0.0176 (6) | 0.0180 (6) | −0.0052 (4) | −0.0014 (4) | −0.0048 (5) |
| C6 | 0.0168 (6) | 0.0181 (6) | 0.0239 (6) | −0.0062 (5) | −0.0027 (5) | −0.0087 (5) |
| C7 | 0.0132 (5) | 0.0189 (6) | 0.0198 (6) | −0.0007 (4) | −0.0044 (4) | −0.0091 (5) |
| C8 | 0.0170 (6) | 0.0147 (5) | 0.0166 (6) | −0.0020 (4) | −0.0044 (4) | −0.0043 (5) |
| C9 | 0.0126 (5) | 0.0142 (5) | 0.0183 (6) | 0.0001 (4) | −0.0027 (4) | −0.0070 (5) |
| C10 | 0.0130 (5) | 0.0165 (5) | 0.0175 (6) | −0.0017 (4) | −0.0012 (4) | −0.0071 (5) |
| C11 | 0.0181 (6) | 0.0127 (5) | 0.0132 (5) | −0.0023 (4) | −0.0032 (4) | −0.0049 (4) |
| C12 | 0.0191 (6) | 0.0170 (5) | 0.0105 (5) | −0.0051 (4) | −0.0019 (4) | −0.0050 (4) |
| C13 | 0.0170 (6) | 0.0216 (6) | 0.0159 (6) | −0.0009 (5) | −0.0045 (4) | −0.0068 (5) |
| C14 | 0.0206 (6) | 0.0165 (6) | 0.0156 (6) | 0.0012 (5) | −0.0029 (5) | −0.0062 (5) |
| C15 | 0.0256 (6) | 0.0141 (6) | 0.0158 (6) | −0.0023 (5) | −0.0021 (5) | −0.0066 (5) |
| C16 | 0.0281 (7) | 0.0160 (6) | 0.0182 (6) | −0.0081 (5) | −0.0041 (5) | −0.0070 (5) |
| C17 | 0.0222 (6) | 0.0181 (6) | 0.0166 (6) | −0.0054 (5) | −0.0062 (5) | −0.0039 (5) |
| C18 | 0.0197 (6) | 0.0145 (5) | 0.0171 (6) | −0.0017 (4) | −0.0063 (5) | −0.0052 (5) |
| C19 | 0.0193 (6) | 0.0140 (5) | 0.0096 (5) | −0.0035 (4) | −0.0031 (4) | −0.0030 (4) |
| C20 | 0.0208 (6) | 0.0141 (5) | 0.0112 (5) | −0.0024 (4) | −0.0029 (4) | −0.0036 (4) |
| C23 | 0.0161 (5) | 0.0138 (5) | 0.0157 (6) | 0.0003 (4) | −0.0041 (4) | −0.0066 (5) |
| C24 | 0.0154 (5) | 0.0116 (5) | 0.0168 (6) | 0.0009 (4) | −0.0058 (4) | −0.0057 (4) |
| C25 | 0.0181 (6) | 0.0171 (6) | 0.0146 (6) | −0.0013 (4) | −0.0034 (4) | −0.0062 (5) |
| C26 | 0.0153 (6) | 0.0183 (6) | 0.0189 (6) | −0.0030 (4) | −0.0023 (4) | −0.0060 (5) |
| C28 | 0.0245 (6) | 0.0207 (6) | 0.0164 (6) | −0.0039 (5) | −0.0065 (5) | −0.0074 (5) |
| C29 | 0.0216 (6) | 0.0172 (6) | 0.0147 (6) | −0.0045 (5) | −0.0037 (5) | −0.0043 (5) |
| C33 | 0.0142 (5) | 0.0144 (5) | 0.0159 (6) | −0.0008 (4) | −0.0029 (4) | −0.0079 (5) |
| C34 | 0.0125 (5) | 0.0165 (5) | 0.0158 (6) | −0.0011 (4) | −0.0016 (4) | −0.0085 (5) |
| C35 | 0.0195 (6) | 0.0192 (6) | 0.0169 (6) | −0.0031 (5) | −0.0046 (5) | −0.0053 (5) |
| C36 | 0.0218 (6) | 0.0190 (6) | 0.0230 (6) | −0.0071 (5) | −0.0027 (5) | −0.0064 (5) |
| C38 | 0.0173 (6) | 0.0229 (6) | 0.0220 (6) | −0.0006 (5) | −0.0073 (5) | −0.0104 (5) |
| C39 | 0.0173 (6) | 0.0162 (6) | 0.0173 (6) | −0.0020 (4) | −0.0043 (4) | −0.0066 (5) |
| N21 | 0.0236 (6) | 0.0162 (5) | 0.0241 (6) | −0.0063 (4) | −0.0107 (4) | −0.0063 (4) |
| N22 | 0.0246 (5) | 0.0150 (5) | 0.0210 (6) | −0.0067 (4) | −0.0129 (4) | −0.0015 (4) |
| N27 | 0.0180 (5) | 0.0182 (5) | 0.0217 (5) | −0.0020 (4) | −0.0071 (4) | −0.0083 (4) |
| N31 | 0.0214 (5) | 0.0198 (5) | 0.0205 (6) | −0.0074 (4) | −0.0076 (4) | −0.0079 (4) |
| N32 | 0.0229 (5) | 0.0174 (5) | 0.0183 (5) | −0.0076 (4) | −0.0107 (4) | −0.0032 (4) |
| N37 | 0.0174 (5) | 0.0232 (5) | 0.0265 (6) | −0.0049 (4) | −0.0042 (4) | −0.0126 (5) |
| O2 | 0.0240 (5) | 0.0212 (5) | 0.0220 (5) | −0.0091 (4) | −0.0088 (4) | −0.0053 (4) |
| O7 | 0.0226 (4) | 0.0211 (4) | 0.0209 (5) | −0.0078 (3) | −0.0087 (4) | −0.0066 (4) |
| O12 | 0.0189 (4) | 0.0197 (4) | 0.0218 (5) | −0.0049 (3) | −0.0054 (3) | −0.0094 (4) |
| O17 | 0.0261 (5) | 0.0225 (5) | 0.0422 (6) | −0.0036 (4) | −0.0175 (4) | −0.0136 (4) |
| O23 | 0.0289 (5) | 0.0214 (4) | 0.0164 (4) | −0.0066 (4) | −0.0089 (4) | −0.0055 (4) |
| O33 | 0.0331 (5) | 0.0196 (5) | 0.0238 (5) | −0.0055 (4) | −0.0176 (4) | −0.0021 (4) |
Geometric parameters (Å, º) top
| C1—C2 | 1.3739 (17) | C23—O23 | 1.2232 (15) |
| C1—C9 | 1.4203 (16) | C23—N22 | 1.3490 (15) |
| C1—H1 | 0.95 | C23—C24 | 1.5001 (16) |
| C2—O2 | 1.3607 (14) | C24—C25 | 1.3899 (17) |
| C2—C3 | 1.4198 (17) | C24—C29 | 1.3913 (17) |
| C3—C4 | 1.3614 (17) | C25—C26 | 1.3846 (17) |
| C3—H3 | 0.95 | C25—H25 | 0.95 |
| C4—C10 | 1.4190 (17) | C26—N27 | 1.3418 (16) |
| C4—H4 | 0.95 | C26—H26 | 0.95 |
| C5—C6 | 1.3670 (18) | C28—N27 | 1.3397 (16) |
| C5—C10 | 1.4141 (16) | C28—C29 | 1.3855 (17) |
| C5—H5 | 0.95 | C28—H28 | 0.95 |
| C6—C7 | 1.4132 (17) | C29—H29 | 0.95 |
| C6—H6 | 0.95 | C33—O33 | 1.2303 (14) |
| C7—O7 | 1.3647 (15) | C33—N32 | 1.3361 (15) |
| C7—C8 | 1.3742 (16) | C33—C34 | 1.5004 (16) |
| C8—C9 | 1.4170 (17) | C34—C39 | 1.3907 (17) |
| C8—H8 | 0.95 | C34—C35 | 1.3913 (17) |
| C9—C10 | 1.4257 (17) | C35—C36 | 1.3840 (17) |
| C11—C12 | 1.3763 (16) | C35—H35 | 0.95 |
| C11—C19 | 1.4188 (16) | C36—N37 | 1.3377 (17) |
| C11—H11 | 0.95 | C36—H36 | 0.95 |
| C12—O12 | 1.3590 (14) | C38—N37 | 1.3386 (17) |
| C12—C13 | 1.4174 (17) | C38—C39 | 1.3807 (17) |
| C13—C14 | 1.3648 (17) | C38—H38 | 0.95 |
| C13—H13 | 0.95 | C39—H39 | 0.95 |
| C14—C20 | 1.4179 (17) | N21—N22 | 1.4194 (14) |
| C14—H14 | 0.95 | N21—H21D | 0.911 (13) |
| C15—C16 | 1.3676 (18) | N21—H21E | 0.905 (13) |
| C15—C20 | 1.4179 (16) | N22—H22D | 0.879 (13) |
| C15—H15 | 0.95 | N31—N32 | 1.4108 (14) |
| C16—C17 | 1.4188 (18) | N31—H31D | 0.908 (13) |
| C16—H16 | 0.95 | N31—H31E | 0.901 (13) |
| C17—O17 | 1.3564 (15) | N32—H32D | 0.871 (13) |
| C17—C18 | 1.3745 (17) | O2—H2D | 0.878 (14) |
| C18—C19 | 1.4169 (16) | O7—H7D | 0.899 (13) |
| C18—H18 | 0.95 | O12—H12D | 0.883 (13) |
| C19—C20 | 1.4256 (16) | O17—H17D | 0.875 (14) |
| C2—C1—C9 | 120.50 (11) | C14—C20—C15 | 122.68 (11) |
| C2—C1—H1 | 119.8 | C14—C20—C19 | 118.56 (11) |
| C9—C1—H1 | 119.8 | C15—C20—C19 | 118.74 (11) |
| O2—C2—C1 | 124.36 (11) | O23—C23—N22 | 122.74 (11) |
| O2—C2—C3 | 115.35 (10) | O23—C23—C24 | 121.09 (10) |
| C1—C2—C3 | 120.29 (11) | N22—C23—C24 | 116.11 (10) |
| C4—C3—C2 | 119.97 (11) | C25—C24—C29 | 118.34 (11) |
| C4—C3—H3 | 120 | C25—C24—C23 | 118.33 (10) |
| C2—C3—H3 | 120 | C29—C24—C23 | 123.15 (11) |
| C3—C4—C10 | 121.64 (11) | C26—C25—C24 | 119.01 (11) |
| C3—C4—H4 | 119.2 | C26—C25—H25 | 120.5 |
| C10—C4—H4 | 119.2 | C24—C25—H25 | 120.5 |
| C6—C5—C10 | 121.32 (11) | N27—C26—C25 | 123.11 (11) |
| C6—C5—H5 | 119.3 | N27—C26—H26 | 118.4 |
| C10—C5—H5 | 119.3 | C25—C26—H26 | 118.4 |
| C5—C6—C7 | 119.63 (11) | N27—C28—C29 | 123.46 (11) |
| C5—C6—H6 | 120.2 | N27—C28—H28 | 118.3 |
| C7—C6—H6 | 120.2 | C29—C28—H28 | 118.3 |
| O7—C7—C8 | 118.47 (11) | C28—C29—C24 | 118.65 (11) |
| O7—C7—C6 | 120.94 (10) | C28—C29—H29 | 120.7 |
| C8—C7—C6 | 120.59 (11) | C24—C29—H29 | 120.7 |
| C7—C8—C9 | 120.73 (11) | O33—C33—N32 | 122.18 (11) |
| C7—C8—H8 | 119.6 | O33—C33—C34 | 121.02 (10) |
| C9—C8—H8 | 119.6 | N32—C33—C34 | 116.79 (10) |
| C8—C9—C1 | 122.21 (11) | C39—C34—C35 | 118.01 (11) |
| C8—C9—C10 | 118.46 (10) | C39—C34—C33 | 124.69 (10) |
| C1—C9—C10 | 119.27 (11) | C35—C34—C33 | 117.29 (10) |
| C5—C10—C4 | 122.52 (11) | C36—C35—C34 | 119.18 (11) |
| C5—C10—C9 | 119.10 (11) | C36—C35—H35 | 120.4 |
| C4—C10—C9 | 118.30 (10) | C34—C35—H35 | 120.4 |
| C12—C11—C19 | 120.17 (11) | N37—C36—C35 | 122.99 (11) |
| C12—C11—H11 | 119.9 | N37—C36—H36 | 118.5 |
| C19—C11—H11 | 119.9 | C35—C36—H36 | 118.5 |
| O12—C12—C11 | 123.25 (11) | N37—C38—C39 | 123.58 (11) |
| O12—C12—C13 | 116.21 (10) | N37—C38—H38 | 118.2 |
| C11—C12—C13 | 120.53 (11) | C39—C38—H38 | 118.2 |
| C14—C13—C12 | 120.05 (11) | C38—C39—C34 | 118.77 (11) |
| C14—C13—H13 | 120 | C38—C39—H39 | 120.6 |
| C12—C13—H13 | 120 | C34—C39—H39 | 120.6 |
| C13—C14—C20 | 121.29 (11) | N22—N21—H21D | 105.9 (10) |
| C13—C14—H14 | 119.4 | N22—N21—H21E | 108.0 (10) |
| C20—C14—H14 | 119.4 | H21D—N21—H21E | 107.8 (14) |
| C16—C15—C20 | 121.66 (11) | C23—N22—N21 | 120.88 (10) |
| C16—C15—H15 | 119.2 | C23—N22—H22D | 121.4 (10) |
| C20—C15—H15 | 119.2 | N21—N22—H22D | 115.3 (10) |
| C15—C16—C17 | 119.46 (11) | C28—N27—C26 | 117.43 (10) |
| C15—C16—H16 | 120.3 | N32—N31—H31D | 107.6 (10) |
| C17—C16—H16 | 120.3 | N32—N31—H31E | 108.0 (10) |
| O17—C17—C18 | 117.97 (11) | H31D—N31—H31E | 106.3 (14) |
| O17—C17—C16 | 121.58 (11) | C33—N32—N31 | 122.86 (10) |
| C18—C17—C16 | 120.44 (11) | C33—N32—H32D | 123.5 (10) |
| C17—C18—C19 | 120.97 (11) | N31—N32—H32D | 113.6 (10) |
| C17—C18—H18 | 119.5 | C36—N37—C38 | 117.46 (11) |
| C19—C18—H18 | 119.5 | C2—O2—H2D | 110.1 (11) |
| C18—C19—C11 | 121.90 (11) | C7—O7—H7D | 112.6 (11) |
| C18—C19—C20 | 118.70 (11) | C12—O12—H12D | 108.6 (11) |
| C11—C19—C20 | 119.40 (11) | C17—O17—H17D | 112.1 (12) |
| C9—C1—C2—O2 | −178.35 (11) | C13—C14—C20—C15 | −178.26 (11) |
| C9—C1—C2—C3 | 1.72 (18) | C13—C14—C20—C19 | 0.35 (17) |
| O2—C2—C3—C4 | 179.30 (11) | C16—C15—C20—C14 | 179.42 (11) |
| C1—C2—C3—C4 | −0.77 (18) | C16—C15—C20—C19 | 0.82 (18) |
| C2—C3—C4—C10 | −0.79 (19) | C18—C19—C20—C14 | 179.41 (11) |
| C10—C5—C6—C7 | 0.94 (18) | C11—C19—C20—C14 | −0.13 (16) |
| C5—C6—C7—O7 | −177.84 (11) | C18—C19—C20—C15 | −1.92 (16) |
| C5—C6—C7—C8 | 2.35 (18) | C11—C19—C20—C15 | 178.54 (10) |
| O7—C7—C8—C9 | 175.35 (10) | O23—C23—C24—C25 | 28.16 (17) |
| C6—C7—C8—C9 | −4.83 (18) | N22—C23—C24—C25 | −154.60 (11) |
| C7—C8—C9—C1 | −173.24 (11) | O23—C23—C24—C29 | −146.79 (12) |
| C7—C8—C9—C10 | 3.98 (17) | N22—C23—C24—C29 | 30.45 (17) |
| C2—C1—C9—C8 | 176.07 (11) | C29—C24—C25—C26 | −0.38 (17) |
| C2—C1—C9—C10 | −1.12 (17) | C23—C24—C25—C26 | −175.57 (10) |
| C6—C5—C10—C4 | 175.12 (12) | C24—C25—C26—N27 | 1.28 (18) |
| C6—C5—C10—C9 | −1.69 (18) | N27—C28—C29—C24 | 0.56 (19) |
| C3—C4—C10—C5 | −175.49 (12) | C25—C24—C29—C28 | −0.48 (17) |
| C3—C4—C10—C9 | 1.35 (18) | C23—C24—C29—C28 | 174.47 (11) |
| C8—C9—C10—C5 | −0.73 (17) | O33—C33—C34—C39 | 178.10 (12) |
| C1—C9—C10—C5 | 176.57 (11) | N32—C33—C34—C39 | −0.95 (17) |
| C8—C9—C10—C4 | −177.69 (11) | O33—C33—C34—C35 | −0.69 (17) |
| C1—C9—C10—C4 | −0.39 (17) | N32—C33—C34—C35 | −179.74 (11) |
| C19—C11—C12—O12 | −179.99 (10) | C39—C34—C35—C36 | −0.57 (18) |
| C19—C11—C12—C13 | 0.33 (17) | C33—C34—C35—C36 | 178.31 (11) |
| O12—C12—C13—C14 | −179.81 (10) | C34—C35—C36—N37 | 0.30 (19) |
| C11—C12—C13—C14 | −0.11 (18) | N37—C38—C39—C34 | 0.43 (19) |
| C12—C13—C14—C20 | −0.24 (18) | C35—C34—C39—C38 | 0.22 (17) |
| C20—C15—C16—C17 | 1.03 (19) | C33—C34—C39—C38 | −178.56 (11) |
| C15—C16—C17—O17 | 177.65 (12) | O23—C23—N22—N21 | 1.55 (19) |
| C15—C16—C17—C18 | −1.77 (18) | C24—C23—N22—N21 | −175.64 (10) |
| O17—C17—C18—C19 | −178.81 (11) | C29—C28—N27—C26 | 0.26 (18) |
| C16—C17—C18—C19 | 0.63 (18) | C25—C26—N27—C28 | −1.20 (18) |
| C17—C18—C19—C11 | −179.26 (11) | O33—C33—N32—N31 | 1.58 (19) |
| C17—C18—C19—C20 | 1.22 (17) | C34—C33—N32—N31 | −179.39 (10) |
| C12—C11—C19—C18 | −179.73 (11) | C35—C36—N37—C38 | 0.33 (19) |
| C12—C11—C19—C20 | −0.21 (17) | C39—C38—N37—C36 | −0.70 (19) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2D···N21i | 0.88 (1) | 1.92 (1) | 2.784 (1) | 170 (1) |
| O7—H7D···N27ii | 0.90 (1) | 1.86 (1) | 2.754 (2) | 170 (1) |
| O12—H12D···N31iii | 0.88 (1) | 1.96 (1) | 2.801 (1) | 160 (1) |
| O17—H17D···N37iv | 0.87 (2) | 1.84 (2) | 2.697 (2) | 169 (2) |
| N21—H21D···O7iv | 0.91 (1) | 2.12 (1) | 3.015 (1) | 167 (1) |
| N21—H21E···O33i | 0.91 (1) | 2.25 (1) | 3.037 (2) | 145 (1) |
| N22—H22D···O33 | 0.88 (1) | 2.16 (1) | 2.939 (1) | 147 (1) |
| N31—H31D···O2i | 0.91 (1) | 2.34 (1) | 3.183 (1) | 154 (1) |
| N31—H31E···O23i | 0.90 (2) | 2.07 (2) | 2.855 (2) | 145 (1) |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) x, y−1, z; (iv) x+1, y, z. |
Naphthalene-2,7-diol; 2-(2-oxopyrrolidin-1-yl)acetamide (II) top
Crystal data top
| C10H8O2·C6H10N2O2 | F(000) = 640 |
| Mr = 302.32 | Dx = 1.381 Mg m−3 |
| Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2c -2ac | Cell parameters from 6581 reflections |
| a = 13.6888 (8) Å | θ = 4.5–29.1° |
| b = 11.0370 (6) Å | µ = 0.1 mm−1 |
| c = 9.6269 (5) Å | T = 130 K |
| V = 1454.46 (14) Å3 | Prism, colourless |
| Z = 4 | 0.55 × 0.4 × 0.23 mm |
Data collection top
| Agilent Xcalibur Atlas Gemini diffractometer | 3665 independent reflections |
| Graphite monochromator | 3276 reflections with I > 2σ(I) |
| Detector resolution: 10.4685 pixels mm-1 | Rint = 0.044 |
| ω scans | θmax = 29.5°, θmin = 3.5° |
| Absorption correction: analytical [CrysAlis PRO (Agilent, 2013), based on expressions derived by Clark & Reid (1995)] | h = −17→17 |
| Tmin = 0.966, Tmax = 0.98 | k = −15→14 |
| 18467 measured reflections | l = −12→13 |
Refinement top
| Refinement on F2 | Hydrogen site location: mixed |
| Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
| R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0343P)2 + 0.2565P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.082 | (Δ/σ)max < 0.001 |
| S = 1.07 | Δρmax = 0.20 e Å−3 |
| 3665 reflections | Δρmin = −0.19 e Å−3 |
| 211 parameters | Absolute structure: Flack x determined using 1333 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
| 5 restraints | Absolute structure parameter: −0.3 (5) |
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 | 0.61096 (15) | 1.00794 (18) | 0.30552 (19) | 0.0193 (4) | |
| H1 | 0.556956 | 1.060957 | 0.317685 | 0.023* | |
| C2 | 0.68607 (15) | 1.03945 (18) | 0.2173 (2) | 0.0206 (4) | |
| C3 | 0.76736 (16) | 0.96208 (19) | 0.1981 (2) | 0.0242 (5) | |
| H3 | 0.818877 | 0.985208 | 0.137478 | 0.029* | |
| C4 | 0.77146 (16) | 0.85429 (19) | 0.2668 (2) | 0.0237 (4) | |
| H4 | 0.826471 | 0.803046 | 0.253848 | 0.028* | |
| C5 | 0.69822 (16) | 0.70453 (19) | 0.4264 (2) | 0.0221 (4) | |
| H5 | 0.751282 | 0.650955 | 0.409945 | 0.027* | |
| C6 | 0.62618 (15) | 0.67080 (18) | 0.5170 (2) | 0.0207 (4) | |
| H6 | 0.628897 | 0.594577 | 0.562669 | 0.025* | |
| C7 | 0.54749 (15) | 0.75128 (19) | 0.5415 (2) | 0.0196 (4) | |
| C8 | 0.54042 (15) | 0.85971 (18) | 0.4731 (2) | 0.0186 (4) | |
| H8 | 0.485803 | 0.91097 | 0.489023 | 0.022* | |
| C9 | 0.61446 (14) | 0.89580 (18) | 0.3784 (2) | 0.0173 (4) | |
| C10 | 0.69557 (15) | 0.81700 (18) | 0.3569 (2) | 0.0195 (4) | |
| C12 | 0.26117 (15) | 0.61573 (17) | 0.2630 (2) | 0.0174 (4) | |
| C13 | 0.35342 (15) | 0.67544 (19) | 0.3215 (2) | 0.0206 (4) | |
| H13A | 0.33736 | 0.758476 | 0.352938 | 0.025* | |
| H13B | 0.37613 | 0.628893 | 0.403211 | 0.025* | |
| C15 | 0.49265 (14) | 0.59022 (18) | 0.1972 (2) | 0.0179 (4) | |
| C16 | 0.56161 (17) | 0.6229 (2) | 0.0820 (2) | 0.0247 (5) | |
| H16A | 0.551507 | 0.569408 | 0.000663 | 0.03* | |
| H16B | 0.630278 | 0.615411 | 0.113105 | 0.03* | |
| C17 | 0.53752 (18) | 0.7540 (2) | 0.0456 (3) | 0.0285 (5) | |
| H17A | 0.526982 | 0.762831 | −0.055629 | 0.034* | |
| H17B | 0.591395 | 0.808418 | 0.074063 | 0.034* | |
| C18 | 0.44351 (15) | 0.78437 (18) | 0.1260 (2) | 0.0222 (4) | |
| H18A | 0.450799 | 0.861024 | 0.178349 | 0.027* | |
| H18B | 0.387092 | 0.791642 | 0.062161 | 0.027* | |
| N11 | 0.18955 (13) | 0.60268 (17) | 0.35590 (18) | 0.0211 (4) | |
| H11E | 0.1374 (16) | 0.558 (2) | 0.327 (2) | 0.025* | |
| H11D | 0.2017 (18) | 0.614 (2) | 0.447 (2) | 0.025* | |
| N14 | 0.43120 (13) | 0.68142 (15) | 0.22042 (18) | 0.0191 (4) | |
| O2 | 0.68941 (12) | 1.14487 (13) | 0.14322 (17) | 0.0261 (3) | |
| H2D | 0.6362 (17) | 1.187 (2) | 0.157 (3) | 0.039* | |
| O7 | 0.47739 (11) | 0.72152 (14) | 0.63771 (17) | 0.0248 (3) | |
| H7D | 0.485 (2) | 0.650 (2) | 0.673 (3) | 0.037* | |
| O12 | 0.25467 (11) | 0.58387 (13) | 0.14121 (16) | 0.0227 (3) | |
| O15 | 0.49125 (11) | 0.49224 (13) | 0.26262 (16) | 0.0221 (3) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0185 (10) | 0.0185 (9) | 0.0210 (10) | 0.0021 (7) | −0.0008 (8) | −0.0030 (8) |
| C2 | 0.0230 (11) | 0.0187 (10) | 0.0202 (10) | −0.0021 (8) | −0.0023 (9) | −0.0036 (8) |
| C3 | 0.0196 (11) | 0.0261 (11) | 0.0269 (10) | −0.0026 (8) | 0.0059 (9) | −0.0055 (9) |
| C4 | 0.0201 (11) | 0.0240 (10) | 0.0270 (11) | 0.0027 (8) | 0.0031 (9) | −0.0069 (9) |
| C5 | 0.0223 (11) | 0.0213 (10) | 0.0227 (10) | 0.0051 (8) | −0.0019 (9) | −0.0036 (8) |
| C6 | 0.0238 (11) | 0.0166 (9) | 0.0218 (10) | 0.0024 (8) | −0.0043 (9) | 0.0004 (8) |
| C7 | 0.0188 (10) | 0.0216 (10) | 0.0184 (10) | −0.0012 (8) | −0.0028 (8) | −0.0019 (8) |
| C8 | 0.0157 (10) | 0.0193 (10) | 0.0209 (10) | 0.0018 (8) | −0.0008 (8) | −0.0030 (8) |
| C9 | 0.0168 (10) | 0.0173 (9) | 0.0177 (10) | −0.0009 (7) | −0.0024 (8) | −0.0051 (8) |
| C10 | 0.0203 (11) | 0.0191 (9) | 0.0190 (10) | 0.0009 (8) | −0.0021 (8) | −0.0051 (8) |
| C12 | 0.0206 (10) | 0.0147 (8) | 0.0170 (9) | 0.0015 (7) | −0.0014 (8) | 0.0006 (8) |
| C13 | 0.0174 (10) | 0.0252 (10) | 0.0191 (10) | 0.0014 (8) | −0.0006 (8) | −0.0032 (8) |
| C15 | 0.0167 (10) | 0.0211 (9) | 0.0159 (9) | 0.0006 (8) | −0.0053 (8) | −0.0038 (8) |
| C16 | 0.0202 (12) | 0.0318 (12) | 0.0221 (11) | 0.0047 (9) | 0.0029 (8) | 0.0016 (9) |
| C17 | 0.0286 (12) | 0.0282 (11) | 0.0287 (12) | −0.0003 (10) | 0.0060 (10) | 0.0041 (10) |
| C18 | 0.0222 (10) | 0.0199 (10) | 0.0246 (11) | 0.0010 (8) | −0.0034 (9) | 0.0025 (9) |
| N11 | 0.0214 (10) | 0.0269 (9) | 0.0150 (9) | −0.0043 (7) | −0.0011 (7) | −0.0002 (7) |
| N14 | 0.0185 (9) | 0.0185 (8) | 0.0202 (9) | 0.0016 (6) | 0.0000 (7) | −0.0003 (7) |
| O2 | 0.0250 (8) | 0.0206 (7) | 0.0329 (8) | 0.0007 (6) | 0.0057 (7) | 0.0029 (7) |
| O7 | 0.0244 (8) | 0.0220 (7) | 0.0281 (8) | 0.0028 (6) | 0.0060 (7) | 0.0058 (7) |
| O12 | 0.0265 (8) | 0.0257 (7) | 0.0159 (7) | −0.0021 (6) | 0.0007 (6) | −0.0019 (6) |
| O15 | 0.0259 (8) | 0.0199 (7) | 0.0206 (7) | 0.0028 (6) | −0.0024 (6) | −0.0003 (6) |
Geometric parameters (Å, º) top
| C1—C2 | 1.378 (3) | C12—C13 | 1.531 (3) |
| C1—C9 | 1.423 (3) | C13—N14 | 1.444 (3) |
| C1—H1 | 0.95 | C13—H13A | 0.99 |
| C2—O2 | 1.366 (2) | C13—H13B | 0.99 |
| C2—C3 | 1.415 (3) | C15—O15 | 1.252 (3) |
| C3—C4 | 1.362 (3) | C15—N14 | 1.331 (3) |
| C3—H3 | 0.95 | C15—C16 | 1.500 (3) |
| C4—C10 | 1.415 (3) | C16—C17 | 1.525 (3) |
| C4—H4 | 0.95 | C16—H16A | 0.99 |
| C5—C6 | 1.368 (3) | C16—H16B | 0.99 |
| C5—C10 | 1.411 (3) | C17—C18 | 1.539 (3) |
| C5—H5 | 0.95 | C17—H17A | 0.99 |
| C6—C7 | 1.416 (3) | C17—H17B | 0.99 |
| C6—H6 | 0.95 | C18—N14 | 1.465 (3) |
| C7—C8 | 1.370 (3) | C18—H18A | 0.99 |
| C7—O7 | 1.373 (3) | C18—H18B | 0.99 |
| C8—C9 | 1.420 (3) | N11—H11E | 0.91 (2) |
| C8—H8 | 0.95 | N11—H11D | 0.90 (2) |
| C9—C10 | 1.425 (3) | O2—H2D | 0.88 (2) |
| C12—O12 | 1.227 (3) | O7—H7D | 0.86 (2) |
| C12—N11 | 1.335 (3) | ||
| C2—C1—C9 | 119.86 (18) | N14—C13—H13A | 109.1 |
| C2—C1—H1 | 120.1 | C12—C13—H13A | 109.1 |
| C9—C1—H1 | 120.1 | N14—C13—H13B | 109.1 |
| O2—C2—C1 | 124.19 (18) | C12—C13—H13B | 109.1 |
| O2—C2—C3 | 114.80 (18) | H13A—C13—H13B | 107.9 |
| C1—C2—C3 | 121.01 (19) | O15—C15—N14 | 124.0 (2) |
| C4—C3—C2 | 119.72 (19) | O15—C15—C16 | 126.09 (18) |
| C4—C3—H3 | 120.1 | N14—C15—C16 | 109.89 (18) |
| C2—C3—H3 | 120.1 | C15—C16—C17 | 105.17 (18) |
| C3—C4—C10 | 121.44 (19) | C15—C16—H16A | 110.7 |
| C3—C4—H4 | 119.3 | C17—C16—H16A | 110.7 |
| C10—C4—H4 | 119.3 | C15—C16—H16B | 110.7 |
| C6—C5—C10 | 121.56 (19) | C17—C16—H16B | 110.7 |
| C6—C5—H5 | 119.2 | H16A—C16—H16B | 108.8 |
| C10—C5—H5 | 119.2 | C16—C17—C18 | 105.80 (18) |
| C5—C6—C7 | 118.95 (19) | C16—C17—H17A | 110.6 |
| C5—C6—H6 | 120.5 | C18—C17—H17A | 110.6 |
| C7—C6—H6 | 120.5 | C16—C17—H17B | 110.6 |
| C8—C7—O7 | 118.95 (18) | C18—C17—H17B | 110.6 |
| C8—C7—C6 | 121.43 (19) | H17A—C17—H17B | 108.7 |
| O7—C7—C6 | 119.61 (19) | N14—C18—C17 | 103.83 (16) |
| C7—C8—C9 | 120.23 (18) | N14—C18—H18A | 111 |
| C7—C8—H8 | 119.9 | C17—C18—H18A | 111 |
| C9—C8—H8 | 119.9 | N14—C18—H18B | 111 |
| C8—C9—C1 | 122.42 (18) | C17—C18—H18B | 111 |
| C8—C9—C10 | 118.54 (18) | H18A—C18—H18B | 109 |
| C1—C9—C10 | 119.04 (18) | C12—N11—H11E | 115.6 (16) |
| C5—C10—C4 | 121.88 (19) | C12—N11—H11D | 120.1 (16) |
| C5—C10—C9 | 119.22 (19) | H11E—N11—H11D | 121 (2) |
| C4—C10—C9 | 118.90 (18) | C15—N14—C13 | 123.01 (18) |
| O12—C12—N11 | 123.8 (2) | C15—N14—C18 | 114.19 (17) |
| O12—C12—C13 | 122.28 (19) | C13—N14—C18 | 122.58 (17) |
| N11—C12—C13 | 113.95 (18) | C2—O2—H2D | 110.4 (18) |
| N14—C13—C12 | 112.35 (17) | C7—O7—H7D | 113.4 (18) |
| C9—C1—C2—O2 | −179.89 (18) | C8—C9—C10—C5 | 2.1 (3) |
| C9—C1—C2—C3 | −0.2 (3) | C1—C9—C10—C5 | −178.54 (18) |
| O2—C2—C3—C4 | −179.8 (2) | C8—C9—C10—C4 | −177.63 (19) |
| C1—C2—C3—C4 | 0.5 (3) | C1—C9—C10—C4 | 1.7 (3) |
| C2—C3—C4—C10 | 0.4 (3) | O12—C12—C13—N14 | −3.9 (3) |
| C10—C5—C6—C7 | −0.3 (3) | N11—C12—C13—N14 | 176.52 (17) |
| C5—C6—C7—C8 | 2.3 (3) | O15—C15—C16—C17 | −176.1 (2) |
| C5—C6—C7—O7 | −176.52 (19) | N14—C15—C16—C17 | 4.4 (2) |
| O7—C7—C8—C9 | 176.74 (18) | C15—C16—C17—C18 | −9.2 (2) |
| C6—C7—C8—C9 | −2.1 (3) | C16—C17—C18—N14 | 10.4 (2) |
| C7—C8—C9—C1 | −179.47 (19) | O15—C15—N14—C13 | −2.2 (3) |
| C7—C8—C9—C10 | −0.1 (3) | C16—C15—N14—C13 | 177.40 (18) |
| C2—C1—C9—C8 | 178.48 (18) | O15—C15—N14—C18 | −176.89 (18) |
| C2—C1—C9—C10 | −0.9 (3) | C16—C15—N14—C18 | 2.7 (2) |
| C6—C5—C10—C4 | 177.8 (2) | C12—C13—N14—C15 | −84.6 (2) |
| C6—C5—C10—C9 | −1.9 (3) | C12—C13—N14—C18 | 89.7 (2) |
| C3—C4—C10—C5 | 178.7 (2) | C17—C18—N14—C15 | −8.4 (2) |
| C3—C4—C10—C9 | −1.5 (3) | C17—C18—N14—C13 | 176.82 (18) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2D···O7i | 0.87 (2) | 1.86 (2) | 2.719 (2) | 166 (3) |
| O2—H2D···O15ii | 0.87 (2) | 1.82 (2) | 2.683 (2) | 174 (2) |
| O7—H7D···O15ii | 0.87 (2) | 1.82 (2) | 2.683 (2) | 174 (2) |
| N11—H11D···O12ii | 0.90 (2) | 1.99 (2) | 2.858 (2) | 161 (2) |
| N11—H11E···O15iii | 0.91 (2) | 2.17 (2) | 3.045 (2) | 162 (2) |
| Symmetry codes: (i) −x, −y, z−1/2; (ii) −x+1/2, y, z+1/2; (iii) x−1/2, −y+1, z. |
