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The title compound, C19H14N2O4, was found to have two crystal polymorphs, in which the molecular structures of the diacetylenic compound are broadly similar. The main structural difference between the polymorphs concerns the intermolecular hydrogen-bonding motifs adopted, namely a one-dimensional zigzag polymer linked by N—H
N(py) (py is pyridine) interactions in polymorph I and a centrosymmetric dimeric motif formed by N—HO=C interactions in polymorph II. The diacetylene cores of the molecules stack along the a and b axes in polymorphs I and II, respectively. It was found that only the molecular arrangement in polymorph II satisfies Baughman's criterion to afford polydiacetylenes (PDAs) by thermal annealing or irradiation with light. This predicted polymerization activity was confirmed by experiment.
N(py) (py is pyridine) interactions in polymorph I and a centrosymmetric dimeric motif formed by N—HO=C interactions in polymorph II. The diacetylene cores of the molecules stack along the a and b axes in polymorphs I and II, respectively. It was found that only the molecular arrangement in polymorph II satisfies Baughman's criterion to afford polydiacetylenes (PDAs) by thermal annealing or irradiation with light. This predicted polymerization activity was confirmed by experiment.Keywords: polymorphs; crystal structure; isonicotinate; polymerization reactivity; thermal annealing; photoirradiation; polydiacetylenes; PDA.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618009373/ky3145sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S2053229618009373/ky31454PyDAUrPh_Isup2.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229618009373/ky31454PyDAUrPh_IIsup3.hkl |
CCDC references: 1455186; 1455185
Computing details top
For both structures, data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXD (Schneider & Sheldrick, 2002); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2014).
6-[(Phenylcarbamoyl)oxy]hexa-2,4-diyn-1-yl pyridine-4-carboxylate (4PyDAUrPh_I) top
Crystal data top
| C19H14N2O4 | F(000) = 696.00 |
| Mr = 334.33 | Dx = 1.391 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
| a = 4.354 (3) Å | Cell parameters from 5141 reflections |
| b = 23.381 (14) Å | θ = 2.2–30.8° |
| c = 15.80 (1) Å | µ = 0.10 mm−1 |
| β = 97.096 (6)° | T = 93 K |
| V = 1596.1 (16) Å3 | Chunk, colorless |
| Z = 4 | 0.20 × 0.15 × 0.02 mm |
Data collection top
| Rigaku Saturn724+ diffractometer | 2925 reflections with F2 > 2.0σ(F2) |
| Detector resolution: 7.111 pixels mm-1 | Rint = 0.042 |
| ω scans | θmax = 27.5°, θmin = 3.1° |
| Absorption correction: numerical (NUMABS; Rigaku, 1999) | h = −5→5 |
| Tmin = 0.993, Tmax = 0.998 | k = −29→30 |
| 12965 measured reflections | l = −20→20 |
| 3652 independent reflections |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.10 | w = 1/[σ2(Fo2) + (0.0669P)2 + 0.4875P] where P = (Fo2 + 2Fc2)/3 |
| 3652 reflections | (Δ/σ)max < 0.001 |
| 230 parameters | Δρmax = 0.33 e Å−3 |
| 0 restraints | Δρmin = −0.29 e Å−3 |
| Primary atom site location: structure-invariant direct methods |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O1 | 1.0425 (3) | 0.50033 (5) | 0.34669 (8) | 0.0330 (3) | |
| O2 | 0.9734 (3) | 0.57237 (5) | 0.25158 (7) | 0.0233 (3) | |
| O3 | 0.4461 (3) | 0.29274 (5) | −0.03970 (7) | 0.0265 (3) | |
| O4 | 0.6278 (3) | 0.32876 (5) | −0.15711 (7) | 0.0262 (3) | |
| N1 | 0.4308 (3) | 0.64650 (6) | 0.48910 (9) | 0.0254 (3) | |
| N2 | 0.7238 (3) | 0.23615 (6) | −0.11284 (9) | 0.0232 (3) | |
| C1 | 0.7506 (4) | 0.58174 (7) | 0.37974 (10) | 0.0210 (3) | |
| C2 | 0.7003 (4) | 0.56091 (7) | 0.45917 (10) | 0.0242 (3) | |
| C3 | 0.5399 (4) | 0.59459 (7) | 0.51124 (10) | 0.0262 (4) | |
| C4 | 0.4724 (4) | 0.66533 (7) | 0.41129 (11) | 0.0280 (4) | |
| C5 | 0.6293 (4) | 0.63482 (7) | 0.35415 (10) | 0.0247 (3) | |
| C6 | 0.9364 (4) | 0.54631 (7) | 0.32564 (10) | 0.0219 (3) | |
| C7 | 1.1601 (4) | 0.54197 (7) | 0.19561 (11) | 0.0251 (4) | |
| C8 | 0.9729 (4) | 0.50141 (7) | 0.14109 (10) | 0.0239 (4) | |
| C9 | 0.8254 (4) | 0.46747 (7) | 0.09631 (10) | 0.0230 (3) | |
| C10 | 0.6536 (4) | 0.42687 (7) | 0.04788 (10) | 0.0239 (3) | |
| C11 | 0.4997 (4) | 0.39053 (7) | 0.00896 (10) | 0.0246 (3) | |
| C12 | 0.2936 (4) | 0.34688 (7) | −0.03250 (11) | 0.0282 (4) | |
| C13 | 0.6048 (4) | 0.28873 (7) | −0.10902 (10) | 0.0213 (3) | |
| C14 | 0.8897 (4) | 0.21431 (7) | −0.17716 (10) | 0.0221 (3) | |
| C15 | 0.9685 (4) | 0.24629 (8) | −0.24560 (11) | 0.0270 (4) | |
| C16 | 1.1272 (4) | 0.22001 (8) | −0.30612 (11) | 0.0317 (4) | |
| C17 | 1.2105 (4) | 0.16291 (8) | −0.29965 (11) | 0.0295 (4) | |
| C18 | 1.1323 (4) | 0.13164 (8) | −0.23101 (11) | 0.0295 (4) | |
| C19 | 0.9725 (4) | 0.15671 (7) | −0.17066 (11) | 0.0259 (4) | |
| H1 | 0.669 (5) | 0.2094 (10) | −0.0692 (15) | 0.051 (7)* | |
| H2 | 0.77441 | 0.5242 | 0.47757 | 0.0291* | |
| H3 | 0.50615 | 0.57994 | 0.56541 | 0.0314* | |
| H4 | 0.39002 | 0.7017 | 0.39397 | 0.0336* | |
| H5 | 0.65258 | 0.64985 | 0.29944 | 0.0297* | |
| H7A | 1.32884 | 0.52119 | 0.23054 | 0.0301* | |
| H7B | 1.25541 | 0.56987 | 0.15959 | 0.0301* | |
| H12A | 0.11687 | 0.34153 | 0.00057 | 0.0339* | |
| H12B | 0.21024 | 0.36033 | −0.09021 | 0.0339* | |
| H15 | 0.91454 | 0.28561 | −0.25088 | 0.0324* | |
| H16 | 1.17973 | 0.24177 | −0.35303 | 0.0381* | |
| H17 | 1.31903 | 0.14551 | −0.34146 | 0.0354* | |
| H18 | 1.18944 | 0.09248 | −0.22544 | 0.0354* | |
| H19 | 0.91837 | 0.13458 | −0.12429 | 0.0310* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0479 (8) | 0.0238 (6) | 0.0283 (7) | 0.0098 (5) | 0.0085 (6) | 0.0020 (5) |
| O2 | 0.0296 (6) | 0.0201 (6) | 0.0214 (6) | −0.0004 (5) | 0.0083 (5) | −0.0023 (4) |
| O3 | 0.0318 (7) | 0.0247 (6) | 0.0240 (6) | −0.0013 (5) | 0.0079 (5) | −0.0027 (5) |
| O4 | 0.0347 (7) | 0.0197 (6) | 0.0241 (6) | −0.0013 (5) | 0.0031 (5) | 0.0010 (5) |
| N1 | 0.0303 (8) | 0.0255 (7) | 0.0212 (7) | 0.0003 (6) | 0.0059 (6) | −0.0021 (6) |
| N2 | 0.0276 (8) | 0.0209 (7) | 0.0219 (7) | −0.0007 (6) | 0.0062 (6) | 0.0027 (5) |
| C1 | 0.0231 (8) | 0.0207 (8) | 0.0187 (7) | −0.0039 (6) | 0.0008 (6) | −0.0027 (6) |
| C2 | 0.0300 (9) | 0.0205 (8) | 0.0221 (8) | 0.0006 (7) | 0.0027 (6) | 0.0024 (6) |
| C3 | 0.0308 (9) | 0.0288 (9) | 0.0193 (8) | −0.0008 (7) | 0.0045 (6) | 0.0024 (6) |
| C4 | 0.0365 (10) | 0.0247 (9) | 0.0233 (8) | 0.0042 (7) | 0.0058 (7) | 0.0009 (7) |
| C5 | 0.0327 (9) | 0.0229 (8) | 0.0193 (7) | 0.0004 (7) | 0.0059 (6) | 0.0017 (6) |
| C6 | 0.0260 (8) | 0.0205 (8) | 0.0189 (7) | −0.0034 (6) | 0.0011 (6) | −0.0020 (6) |
| C7 | 0.0293 (9) | 0.0225 (8) | 0.0250 (8) | −0.0020 (7) | 0.0095 (7) | −0.0055 (6) |
| C8 | 0.0303 (9) | 0.0208 (8) | 0.0220 (8) | 0.0018 (6) | 0.0081 (7) | 0.0003 (6) |
| C9 | 0.0266 (9) | 0.0216 (8) | 0.0215 (8) | 0.0025 (6) | 0.0057 (6) | 0.0002 (6) |
| C10 | 0.0263 (9) | 0.0234 (8) | 0.0224 (8) | 0.0046 (7) | 0.0053 (6) | −0.0004 (6) |
| C11 | 0.0248 (8) | 0.0250 (8) | 0.0244 (8) | 0.0040 (7) | 0.0053 (6) | −0.0013 (6) |
| C12 | 0.0272 (9) | 0.0279 (9) | 0.0296 (9) | 0.0012 (7) | 0.0039 (7) | −0.0070 (7) |
| C13 | 0.0215 (8) | 0.0235 (8) | 0.0190 (7) | −0.0051 (6) | 0.0030 (6) | −0.0039 (6) |
| C14 | 0.0219 (8) | 0.0256 (8) | 0.0186 (7) | −0.0027 (6) | 0.0016 (6) | −0.0024 (6) |
| C15 | 0.0318 (10) | 0.0239 (9) | 0.0261 (8) | −0.0019 (7) | 0.0065 (7) | 0.0024 (6) |
| C16 | 0.0408 (11) | 0.0306 (9) | 0.0255 (8) | −0.0013 (8) | 0.0105 (8) | 0.0048 (7) |
| C17 | 0.0365 (10) | 0.0297 (9) | 0.0232 (8) | 0.0009 (7) | 0.0072 (7) | −0.0032 (7) |
| C18 | 0.0368 (10) | 0.0240 (8) | 0.0276 (9) | 0.0035 (7) | 0.0032 (7) | −0.0019 (7) |
| C19 | 0.0305 (9) | 0.0230 (8) | 0.0243 (8) | −0.0019 (7) | 0.0041 (7) | 0.0037 (6) |
Geometric parameters (Å, º) top
| O1—C6 | 1.201 (2) | C14—C15 | 1.392 (3) |
| O2—C6 | 1.346 (2) | C14—C19 | 1.395 (2) |
| O2—C7 | 1.458 (2) | C15—C16 | 1.390 (3) |
| O3—C12 | 1.440 (2) | C16—C17 | 1.384 (3) |
| O3—C13 | 1.368 (2) | C17—C18 | 1.385 (3) |
| O4—C13 | 1.217 (2) | C18—C19 | 1.379 (3) |
| N1—C3 | 1.334 (2) | N2—H1 | 0.98 (2) |
| N1—C4 | 1.339 (2) | C2—H2 | 0.950 |
| N2—C13 | 1.338 (2) | C3—H3 | 0.950 |
| N2—C14 | 1.413 (2) | C4—H4 | 0.950 |
| C1—C2 | 1.389 (2) | C5—H5 | 0.950 |
| C1—C5 | 1.389 (2) | C7—H7A | 0.990 |
| C1—C6 | 1.497 (2) | C7—H7B | 0.990 |
| C2—C3 | 1.388 (2) | C12—H12A | 0.990 |
| C4—C5 | 1.394 (3) | C12—H12B | 0.990 |
| C7—C8 | 1.460 (2) | C15—H15 | 0.950 |
| C8—C9 | 1.196 (2) | C16—H16 | 0.950 |
| C9—C10 | 1.380 (2) | C17—H17 | 0.950 |
| C10—C11 | 1.203 (2) | C18—H18 | 0.950 |
| C11—C12 | 1.460 (2) | C19—H19 | 0.950 |
| O1···C2 | 2.835 (2) | C9···H17iii | 3.4700 |
| O1···C7 | 2.685 (3) | C9···H18iii | 3.3623 |
| O1···C8 | 3.225 (3) | C10···H7Biv | 3.3509 |
| O2···C5 | 2.757 (2) | C10···H12Ai | 2.9969 |
| O2···C9 | 3.472 (2) | C10···H17xiii | 2.9448 |
| O3···C10 | 3.501 (3) | C11···H7Biv | 3.1284 |
| O3···C14 | 3.584 (2) | C11···H12Ai | 2.9391 |
| O4···C11 | 3.105 (2) | C11···H17xiii | 2.7155 |
| O4···C12 | 2.623 (2) | C12···H7Bvii | 3.5141 |
| O4···C14 | 2.941 (2) | C12···H7Biv | 3.5568 |
| O4···C15 | 2.896 (2) | C12···H12Ai | 3.5602 |
| N1···C1 | 2.795 (2) | C12···H16xiii | 3.5958 |
| N2···C12 | 3.523 (3) | C12···H17xiii | 3.0120 |
| C2···C4 | 2.708 (3) | C13···H5vii | 3.3966 |
| C3···C5 | 2.727 (3) | C13···H7Biv | 3.4726 |
| C6···C8 | 3.121 (3) | C13···H12Ai | 2.9222 |
| C11···C13 | 3.092 (3) | C13···H12Bi | 3.1058 |
| C13···C15 | 2.999 (3) | C13···H15vi | 3.5210 |
| C14···C17 | 2.794 (3) | C15···H4vii | 2.9167 |
| C15···C18 | 2.776 (3) | C15···H5iv | 3.1126 |
| C16···C19 | 2.753 (3) | C16···H4vii | 3.0945 |
| O1···C2i | 3.480 (2) | C16···H4iv | 3.2275 |
| O1···C2ii | 3.444 (3) | C16···H5iv | 3.1881 |
| O1···C3ii | 3.502 (2) | C16···H12Axiv | 3.3715 |
| O1···C18iii | 3.361 (3) | C17···H12Axiv | 3.1341 |
| O2···O4iv | 3.351 (2) | C18···H3xi | 3.1253 |
| O2···C5i | 3.431 (2) | C19···H1i | 3.48 (2) |
| O3···N1v | 3.537 (3) | C19···H3v | 3.3446 |
| O3···N2vi | 3.475 (2) | C19···H3xi | 3.1949 |
| O3···C4v | 3.597 (3) | H1···N1v | 2.02 (2) |
| O3···C14vi | 3.557 (2) | H1···C3v | 3.01 (2) |
| O4···O2iv | 3.351 (2) | H1···C4v | 2.84 (2) |
| O4···C5vii | 3.288 (3) | H1···C19vi | 3.48 (2) |
| O4···C7iv | 3.240 (3) | H1···H3v | 3.1249 |
| O4···C12i | 3.324 (2) | H1···H4v | 2.8172 |
| O4···C15vi | 3.595 (2) | H2···O1ii | 2.8508 |
| N1···O3viii | 3.537 (3) | H2···C2xii | 3.1210 |
| N1···N2viii | 2.999 (2) | H2···C2ii | 3.1025 |
| N1···C1vi | 3.575 (3) | H2···C3xii | 3.1109 |
| N1···C19viii | 3.551 (3) | H2···H2xii | 2.8127 |
| N2···O3i | 3.475 (2) | H2···H2ii | 2.3017 |
| N2···N1v | 2.999 (2) | H2···H3i | 3.5613 |
| C1···N1i | 3.575 (3) | H2···H3xii | 2.7707 |
| C2···O1vi | 3.480 (2) | H3···O1xii | 3.4608 |
| C2···O1ii | 3.444 (3) | H3···O1ii | 2.9392 |
| C3···O1ii | 3.502 (2) | H3···C2xii | 3.4230 |
| C3···C19ix | 3.412 (3) | H3···C18ix | 3.1253 |
| C4···O3viii | 3.597 (3) | H3···C19viii | 3.3446 |
| C5···O2vi | 3.431 (2) | H3···C19ix | 3.1949 |
| C5···O4vii | 3.288 (3) | H3···H1viii | 3.1249 |
| C7···O4iv | 3.240 (3) | H3···H2vi | 3.5613 |
| C12···O4vi | 3.324 (2) | H3···H2xii | 2.7707 |
| C12···C13vi | 3.378 (3) | H3···H18ix | 2.7217 |
| C13···C12i | 3.378 (3) | H3···H19viii | 2.5177 |
| C13···C15vi | 3.441 (3) | H3···H19ix | 2.8635 |
| C14···O3i | 3.557 (2) | H4···O3viii | 3.1520 |
| C14···C17vi | 3.539 (3) | H4···C15vii | 2.9167 |
| C15···O4i | 3.595 (2) | H4···C16vii | 3.0945 |
| C15···C13i | 3.441 (3) | H4···C16iv | 3.2275 |
| C17···C14i | 3.539 (3) | H4···H1viii | 2.8172 |
| C18···O1x | 3.361 (3) | H4···H5vi | 3.5812 |
| C19···N1v | 3.551 (3) | H4···H15vii | 2.4934 |
| C19···C3xi | 3.412 (3) | H4···H16vii | 2.8147 |
| O1···H2 | 2.5586 | H4···H16iv | 2.4442 |
| O1···H7A | 2.3927 | H5···O2vi | 3.4708 |
| O1···H7B | 3.5942 | H5···O4vii | 2.4737 |
| O2···H5 | 2.4628 | H5···C7vi | 3.5751 |
| O3···H1 | 2.25 (2) | H5···C13vii | 3.3966 |
| O4···H1 | 3.11 (2) | H5···C15iv | 3.1126 |
| O4···H12A | 3.5517 | H5···C16iv | 3.1881 |
| O4···H12B | 2.3330 | H5···H4i | 3.5812 |
| O4···H15 | 2.2865 | H5···H7Avi | 3.4412 |
| N1···H2 | 3.2428 | H5···H7Bvi | 3.2289 |
| N1···H5 | 3.2608 | H5···H12Bvii | 3.4394 |
| N2···H15 | 2.6890 | H5···H15vii | 2.9146 |
| N2···H19 | 2.5353 | H5···H15iv | 2.6029 |
| C1···H3 | 3.2422 | H5···H16iv | 2.7420 |
| C1···H4 | 3.2356 | H7A···O1i | 3.4427 |
| C2···H5 | 3.2568 | H7A···O2i | 3.0310 |
| C3···H4 | 3.1355 | H7A···C1i | 3.1407 |
| C4···H3 | 3.1382 | H7A···C5i | 3.4573 |
| C5···H2 | 3.2537 | H7A···C6i | 2.9357 |
| C6···H2 | 2.6354 | H7A···C8i | 3.3246 |
| C6···H5 | 2.7263 | H7A···C9i | 3.4472 |
| C6···H7A | 2.4812 | H7A···H5i | 3.4412 |
| C6···H7B | 3.1648 | H7A···H18iii | 2.8319 |
| C9···H7A | 3.1194 | H7B···O2i | 3.2810 |
| C9···H7B | 3.1263 | H7B···O4iv | 2.4253 |
| C10···H12A | 3.0934 | H7B···C8i | 3.5540 |
| C10···H12B | 3.1411 | H7B···C10iv | 3.3509 |
| C13···H12A | 3.1535 | H7B···C11iv | 3.1284 |
| C13···H12B | 2.4430 | H7B···C12vii | 3.5141 |
| C13···H15 | 2.7558 | H7B···C12iv | 3.5568 |
| C14···H16 | 3.2550 | H7B···C13iv | 3.4726 |
| C14···H18 | 3.2627 | H7B···H5i | 3.2289 |
| C15···H1 | 3.33 (3) | H7B···H12Avii | 3.5084 |
| C15···H17 | 3.2781 | H7B···H12Bvii | 2.7251 |
| C15···H19 | 3.2629 | H7B···H12Biv | 3.1477 |
| C16···H18 | 3.2409 | H12A···O3vi | 3.1266 |
| C17···H15 | 3.2755 | H12A···O4vi | 3.0853 |
| C17···H19 | 3.2562 | H12A···N2vi | 3.3841 |
| C18···H16 | 3.2385 | H12A···C10vi | 2.9969 |
| C19···H1 | 2.52 (2) | H12A···C11vi | 2.9391 |
| C19···H15 | 3.2671 | H12A···C12vi | 3.5602 |
| C19···H17 | 3.2609 | H12A···C13vi | 2.9222 |
| H1···H19 | 2.2875 | H12A···C16xiii | 3.3715 |
| H2···H3 | 2.3215 | H12A···C17xiii | 3.1341 |
| H4···H5 | 2.3300 | H12A···H7Bvii | 3.5084 |
| H15···H16 | 2.3343 | H12A···H16xiii | 3.0103 |
| H16···H17 | 2.3322 | H12A···H17xiii | 2.5599 |
| H17···H18 | 2.3391 | H12B···O2vii | 3.0186 |
| H18···H19 | 2.3199 | H12B···O4vi | 2.7258 |
| O1···H2ii | 2.8508 | H12B···N2vi | 3.5855 |
| O1···H3xii | 3.4608 | H12B···C7vii | 3.1509 |
| O1···H3ii | 2.9392 | H12B···C8vii | 3.4019 |
| O1···H7Avi | 3.4427 | H12B···C13vi | 3.1058 |
| O1···H18iii | 2.5684 | H12B···H5vii | 3.4394 |
| O1···H19iii | 3.2424 | H12B···H7Bvii | 2.7251 |
| O2···H5i | 3.4708 | H12B···H7Biv | 3.1477 |
| O2···H7Avi | 3.0310 | H12B···H15vi | 3.2166 |
| O2···H7Bvi | 3.2810 | H15···O2iv | 3.3564 |
| O2···H12Bvii | 3.0186 | H15···O4i | 3.4236 |
| O2···H15iv | 3.3564 | H15···C4vii | 3.0859 |
| O3···H4v | 3.1520 | H15···C5vii | 3.2827 |
| O3···H12Ai | 3.1266 | H15···C5iv | 3.2967 |
| O3···H16xiii | 3.3971 | H15···C13i | 3.5210 |
| O3···H17xiii | 3.5538 | H15···H4vii | 2.4934 |
| O4···H5vii | 2.4737 | H15···H5vii | 2.9146 |
| O4···H7Biv | 2.4253 | H15···H5iv | 2.6029 |
| O4···H12Ai | 3.0853 | H15···H12Bi | 3.2166 |
| O4···H12Bi | 2.7258 | H15···H16vi | 3.5519 |
| O4···H15vi | 3.4236 | H16···O3xiv | 3.3971 |
| N1···H1viii | 2.02 (2) | H16···C4iv | 2.8641 |
| N1···H19viii | 2.7845 | H16···C5iv | 3.0034 |
| N1···H19ix | 3.3429 | H16···C12xiv | 3.5958 |
| N2···H12Ai | 3.3841 | H16···H4vii | 2.8147 |
| N2···H12Bi | 3.5855 | H16···H4iv | 2.4442 |
| C1···H7Avi | 3.1407 | H16···H5iv | 2.7420 |
| C2···H2xii | 3.1210 | H16···H12Axiv | 3.0103 |
| C2···H2ii | 3.1025 | H16···H15i | 3.5519 |
| C2···H3xii | 3.4230 | H17···O3xiv | 3.5538 |
| C2···H19ix | 3.3852 | H17···C9x | 3.4700 |
| C3···H1viii | 3.01 (2) | H17···C10xiv | 2.9448 |
| C3···H2xii | 3.1109 | H17···C11xiv | 2.7155 |
| C3···H18ix | 3.4437 | H17···C12xiv | 3.0120 |
| C3···H19viii | 2.9877 | H17···H12Axiv | 2.5599 |
| C3···H19ix | 2.9304 | H18···O1x | 2.5684 |
| C4···H1viii | 2.84 (2) | H18···C3xi | 3.4437 |
| C4···H15vii | 3.0859 | H18···C6x | 3.5517 |
| C4···H16iv | 2.8641 | H18···C7x | 3.3786 |
| C5···H7Avi | 3.4573 | H18···C8x | 3.1087 |
| C5···H15vii | 3.2827 | H18···C9x | 3.3623 |
| C5···H15iv | 3.2967 | H18···H3xi | 2.7217 |
| C5···H16iv | 3.0034 | H18···H7Ax | 2.8319 |
| C6···H7Avi | 2.9357 | H18···H19i | 3.5132 |
| C6···H18iii | 3.5517 | H19···O1x | 3.2424 |
| C7···H5i | 3.5751 | H19···N1v | 2.7845 |
| C7···H12Bvii | 3.1509 | H19···N1xi | 3.3429 |
| C7···H18iii | 3.3786 | H19···C2xi | 3.3852 |
| C8···H7Avi | 3.3246 | H19···C3v | 2.9877 |
| C8···H7Bvi | 3.5540 | H19···C3xi | 2.9304 |
| C8···H12Bvii | 3.4019 | H19···H3v | 2.5177 |
| C8···H18iii | 3.1087 | H19···H3xi | 2.8635 |
| C9···H7Avi | 3.4472 | H19···H18vi | 3.5132 |
| C6—O2—C7 | 116.23 (13) | C13—N2—H1 | 115.1 (14) |
| C12—O3—C13 | 114.00 (13) | C14—N2—H1 | 117.7 (14) |
| C3—N1—C4 | 117.10 (15) | C1—C2—H2 | 120.526 |
| C13—N2—C14 | 126.84 (14) | C3—C2—H2 | 120.537 |
| C2—C1—C5 | 118.66 (15) | N1—C3—H3 | 118.324 |
| C2—C1—C6 | 118.59 (15) | C2—C3—H3 | 118.333 |
| C5—C1—C6 | 122.74 (15) | N1—C4—H4 | 118.005 |
| C1—C2—C3 | 118.94 (15) | C5—C4—H4 | 117.997 |
| N1—C3—C2 | 123.34 (16) | C1—C5—H5 | 121.056 |
| N1—C4—C5 | 124.00 (15) | C4—C5—H5 | 121.054 |
| C1—C5—C4 | 117.89 (15) | O2—C7—H7A | 109.397 |
| O1—C6—O2 | 124.24 (16) | O2—C7—H7B | 109.401 |
| O1—C6—C1 | 123.62 (16) | C8—C7—H7A | 109.385 |
| O2—C6—C1 | 112.13 (14) | C8—C7—H7B | 109.386 |
| O2—C7—C8 | 111.21 (14) | H7A—C7—H7B | 108.006 |
| C7—C8—C9 | 178.51 (18) | O3—C12—H12A | 109.066 |
| C8—C9—C10 | 177.41 (18) | O3—C12—H12B | 109.057 |
| C9—C10—C11 | 177.09 (18) | C11—C12—H12A | 109.049 |
| C10—C11—C12 | 174.81 (18) | C11—C12—H12B | 109.045 |
| O3—C12—C11 | 112.70 (14) | H12A—C12—H12B | 107.808 |
| O3—C13—O4 | 122.38 (15) | C14—C15—H15 | 120.390 |
| O3—C13—N2 | 109.61 (14) | C16—C15—H15 | 120.394 |
| O4—C13—N2 | 128.01 (16) | C15—C16—H16 | 119.209 |
| N2—C14—C15 | 124.16 (16) | C17—C16—H16 | 119.221 |
| N2—C14—C19 | 116.52 (15) | C16—C17—H17 | 120.669 |
| C15—C14—C19 | 119.31 (16) | C18—C17—H17 | 120.664 |
| C14—C15—C16 | 119.22 (17) | C17—C18—H18 | 119.637 |
| C15—C16—C17 | 121.57 (17) | C19—C18—H18 | 119.633 |
| C16—C17—C18 | 118.67 (18) | C14—C19—H19 | 119.748 |
| C17—C18—C19 | 120.73 (17) | C18—C19—H19 | 119.750 |
| C14—C19—C18 | 120.50 (16) | ||
| C6—O2—C7—C8 | 85.95 (15) | C2—C1—C6—O2 | −178.37 (13) |
| C7—O2—C6—O1 | −1.1 (2) | C6—C1—C2—C3 | 177.21 (12) |
| C7—O2—C6—C1 | 178.07 (11) | C5—C1—C6—O1 | −179.88 (14) |
| C12—O3—C13—O4 | 3.93 (19) | C5—C1—C6—O2 | 0.9 (2) |
| C12—O3—C13—N2 | −176.65 (11) | C6—C1—C5—C4 | −177.01 (13) |
| C13—O3—C12—C11 | −83.66 (15) | C1—C2—C3—N1 | −0.2 (2) |
| C3—N1—C4—C5 | −2.0 (2) | N1—C4—C5—C1 | −0.2 (2) |
| C4—N1—C3—C2 | 2.2 (2) | N2—C14—C15—C16 | −178.76 (13) |
| C13—N2—C14—C15 | 3.5 (2) | N2—C14—C19—C18 | 179.42 (12) |
| C13—N2—C14—C19 | −175.56 (13) | C15—C14—C19—C18 | 0.4 (2) |
| C14—N2—C13—O3 | 176.67 (13) | C19—C14—C15—C16 | 0.2 (2) |
| C14—N2—C13—O4 | −4.0 (3) | C14—C15—C16—C17 | −0.4 (2) |
| C2—C1—C5—C4 | 2.3 (2) | C15—C16—C17—C18 | 0.1 (3) |
| C5—C1—C2—C3 | −2.1 (2) | C16—C17—C18—C19 | 0.5 (2) |
| C2—C1—C6—O1 | 0.8 (2) | C17—C18—C19—C14 | −0.8 (2) |
| Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+1; (iii) x, −y+1/2, z+1/2; (iv) −x+2, −y+1, −z; (v) −x+1, y−1/2, −z+1/2; (vi) x−1, y, z; (vii) −x+1, −y+1, −z; (viii) −x+1, y+1/2, −z+1/2; (ix) −x+2, y+1/2, −z+1/2; (x) x, −y+1/2, z−1/2; (xi) −x+2, y−1/2, −z+1/2; (xii) −x+1, −y+1, −z+1; (xiii) x−1, −y+1/2, z+1/2; (xiv) x+1, −y+1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H1···N1v | 0.98 (2) | 2.02 (2) | 2.999 (2) | 173 (2) |
| Symmetry code: (v) −x+1, y−1/2, −z+1/2. |
6-[(Phenylcarbamoyl)oxy]hexa-2,4-diyn-1-yl pyridine-4-carboxylate (4PyDAUrPh_II) top
Crystal data top
| C19H14N2O4 | F(000) = 696.00 |
| Mr = 334.33 | Dx = 1.398 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
| a = 19.861 (9) Å | Cell parameters from 3055 reflections |
| b = 5.160 (2) Å | θ = 2.5–31.1° |
| c = 16.451 (8) Å | µ = 0.10 mm−1 |
| β = 109.589 (8)° | T = 93 K |
| V = 1588.4 (12) Å3 | Chip, colorless |
| Z = 4 | 0.25 × 0.10 × 0.01 mm |
Data collection top
| Rigaku Saturn724+ diffractometer | 1701 reflections with F2 > 2.0σ(F2) |
| Detector resolution: 7.111 pixels mm-1 | Rint = 0.080 |
| ω scans | θmax = 25.0°, θmin = 3.2° |
| Absorption correction: numerical (NUMABS; Rigaku, 1999) | h = −23→22 |
| Tmin = 0.868, Tmax = 0.999 | k = −6→6 |
| 10083 measured reflections | l = −19→17 |
| 2764 independent reflections |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0697P)2 + 0.0924P] where P = (Fo2 + 2Fc2)/3 |
| 2764 reflections | (Δ/σ)max < 0.001 |
| 230 parameters | Δρmax = 0.29 e Å−3 |
| 0 restraints | Δρmin = −0.23 e Å−3 |
| Primary atom site location: structure-invariant direct methods |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.76629 (12) | 0.2500 (5) | 1.15967 (14) | 0.0308 (6) | |
| O2 | 0.74045 (12) | −0.1227 (4) | 1.08436 (13) | 0.0285 (6) | |
| O3 | 0.38466 (11) | 0.7018 (4) | 0.79457 (13) | 0.0251 (6) | |
| O4 | 0.40138 (12) | 0.3828 (5) | 0.70838 (14) | 0.0354 (7) | |
| N1 | 0.99923 (15) | −0.0190 (6) | 1.12415 (18) | 0.0336 (8) | |
| N2 | 0.29392 (14) | 0.4418 (6) | 0.72903 (17) | 0.0239 (7) | |
| C1 | 0.85860 (17) | 0.0299 (6) | 1.12422 (19) | 0.0228 (7) | |
| C2 | 0.91182 (17) | 0.1947 (7) | 1.1729 (2) | 0.0266 (8) | |
| C3 | 0.98070 (19) | 0.1621 (7) | 1.1715 (2) | 0.0334 (9) | |
| C4 | 0.94648 (19) | −0.1745 (7) | 1.0776 (2) | 0.0318 (9) | |
| C5 | 0.87637 (18) | −0.1586 (7) | 1.0755 (2) | 0.0287 (8) | |
| C6 | 0.78429 (17) | 0.0676 (7) | 1.12572 (19) | 0.0249 (8) | |
| C7 | 0.66792 (17) | −0.1100 (7) | 1.0853 (2) | 0.0295 (8) | |
| C8 | 0.62442 (18) | 0.0824 (7) | 1.0244 (2) | 0.0261 (8) | |
| C9 | 0.58682 (17) | 0.2366 (7) | 0.9761 (2) | 0.0255 (8) | |
| C10 | 0.54284 (17) | 0.4173 (7) | 0.92161 (19) | 0.0247 (8) | |
| C11 | 0.50530 (17) | 0.5761 (7) | 0.8743 (2) | 0.0245 (8) | |
| C12 | 0.45933 (17) | 0.7656 (7) | 0.8158 (2) | 0.0264 (8) | |
| C13 | 0.36301 (17) | 0.4945 (6) | 0.74029 (19) | 0.0220 (7) | |
| C14 | 0.25181 (17) | 0.2418 (6) | 0.67838 (18) | 0.0204 (7) | |
| C15 | 0.27613 (17) | 0.0683 (6) | 0.62993 (18) | 0.0237 (8) | |
| C16 | 0.23148 (18) | −0.1292 (7) | 0.58549 (19) | 0.0278 (8) | |
| C17 | 0.16278 (18) | −0.1551 (7) | 0.5878 (2) | 0.0282 (8) | |
| C18 | 0.13791 (19) | 0.0217 (7) | 0.6345 (2) | 0.0295 (8) | |
| C19 | 0.18167 (17) | 0.2206 (7) | 0.6792 (2) | 0.0273 (8) | |
| H1 | 0.2752 (19) | 0.555 (7) | 0.755 (2) | 0.035 (10)* | |
| H2 | 0.90133 | 0.32793 | 1.20671 | 0.0319* | |
| H3 | 1.01696 | 0.27439 | 1.20608 | 0.0401* | |
| H4 | 0.95794 | −0.30486 | 1.04357 | 0.0382* | |
| H5 | 0.84121 | −0.27501 | 1.04125 | 0.0345* | |
| H7A | 0.66897 | −0.06573 | 1.1443 | 0.0354* | |
| H7B | 0.64537 | −0.28268 | 1.07063 | 0.0354* | |
| H12A | 0.46826 | 0.939 | 0.84314 | 0.0317* | |
| H12B | 0.4714 | 0.77338 | 0.76219 | 0.0317* | |
| H15 | 0.32297 | 0.08466 | 0.62723 | 0.0285* | |
| H16 | 0.24838 | −0.24888 | 0.55289 | 0.0333* | |
| H17 | 0.13298 | −0.29249 | 0.55759 | 0.0339* | |
| H18 | 0.09066 | 0.00631 | 0.636 | 0.0354* | |
| H19 | 0.16412 | 0.34277 | 0.71043 | 0.0328* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0303 (14) | 0.0309 (15) | 0.0310 (13) | 0.0024 (11) | 0.0098 (11) | −0.0039 (11) |
| O2 | 0.0251 (13) | 0.0236 (14) | 0.0330 (13) | 0.0011 (11) | 0.0047 (11) | −0.0030 (11) |
| O3 | 0.0199 (13) | 0.0262 (14) | 0.0271 (12) | −0.0017 (10) | 0.0049 (10) | −0.0014 (10) |
| O4 | 0.0272 (14) | 0.0462 (17) | 0.0354 (14) | −0.0027 (12) | 0.0140 (12) | −0.0131 (12) |
| N1 | 0.0312 (18) | 0.038 (2) | 0.0307 (17) | 0.0060 (15) | 0.0092 (14) | 0.0027 (14) |
| N2 | 0.0244 (17) | 0.0227 (17) | 0.0253 (15) | −0.0004 (13) | 0.0093 (13) | −0.0010 (13) |
| C1 | 0.0238 (17) | 0.0233 (19) | 0.0194 (17) | 0.0007 (15) | 0.0046 (14) | 0.0062 (14) |
| C2 | 0.029 (2) | 0.026 (2) | 0.0261 (18) | −0.0002 (16) | 0.0100 (15) | −0.0005 (15) |
| C3 | 0.028 (2) | 0.037 (2) | 0.032 (2) | −0.0038 (18) | 0.0069 (17) | −0.0006 (17) |
| C4 | 0.035 (2) | 0.035 (2) | 0.0250 (19) | 0.0078 (18) | 0.0089 (16) | 0.0003 (16) |
| C5 | 0.023 (2) | 0.029 (2) | 0.0288 (19) | 0.0057 (16) | 0.0025 (15) | −0.0014 (15) |
| C6 | 0.029 (2) | 0.023 (2) | 0.0173 (17) | 0.0039 (16) | 0.0002 (15) | 0.0033 (15) |
| C7 | 0.0235 (19) | 0.029 (2) | 0.0312 (19) | 0.0000 (16) | 0.0028 (15) | 0.0033 (16) |
| C8 | 0.0258 (19) | 0.027 (2) | 0.0255 (18) | −0.0022 (16) | 0.0078 (16) | −0.0038 (16) |
| C9 | 0.0226 (19) | 0.030 (2) | 0.0225 (17) | −0.0014 (16) | 0.0056 (15) | −0.0005 (15) |
| C10 | 0.0225 (19) | 0.029 (2) | 0.0207 (17) | −0.0020 (16) | 0.0048 (15) | −0.0032 (15) |
| C11 | 0.0225 (19) | 0.029 (2) | 0.0245 (18) | −0.0058 (16) | 0.0105 (15) | −0.0061 (16) |
| C12 | 0.0230 (19) | 0.027 (2) | 0.0261 (18) | 0.0000 (16) | 0.0039 (15) | 0.0028 (15) |
| C13 | 0.0217 (18) | 0.024 (2) | 0.0194 (17) | −0.0013 (15) | 0.0059 (14) | 0.0045 (14) |
| C14 | 0.0242 (19) | 0.0159 (18) | 0.0178 (16) | −0.0029 (14) | 0.0028 (14) | 0.0045 (14) |
| C15 | 0.0242 (19) | 0.0245 (19) | 0.0209 (17) | 0.0030 (16) | 0.0055 (15) | 0.0031 (15) |
| C16 | 0.034 (2) | 0.025 (2) | 0.0214 (18) | 0.0067 (17) | 0.0048 (16) | 0.0003 (15) |
| C17 | 0.033 (2) | 0.0192 (19) | 0.0257 (18) | −0.0027 (16) | 0.0011 (15) | 0.0026 (15) |
| C18 | 0.027 (2) | 0.029 (2) | 0.0318 (19) | −0.0056 (17) | 0.0092 (16) | −0.0008 (16) |
| C19 | 0.029 (2) | 0.026 (2) | 0.0293 (18) | −0.0001 (16) | 0.0133 (16) | −0.0024 (15) |
Geometric parameters (Å, º) top
| O1—C6 | 1.208 (4) | C14—C15 | 1.389 (5) |
| O2—C6 | 1.337 (4) | C14—C19 | 1.402 (5) |
| O2—C7 | 1.448 (4) | C15—C16 | 1.387 (4) |
| O3—C12 | 1.443 (4) | C16—C17 | 1.384 (5) |
| O3—C13 | 1.367 (4) | C17—C18 | 1.387 (5) |
| O4—C13 | 1.207 (5) | C18—C19 | 1.386 (5) |
| N1—C3 | 1.345 (5) | N2—H1 | 0.88 (4) |
| N1—C4 | 1.338 (4) | C2—H2 | 0.950 |
| N2—C13 | 1.349 (4) | C3—H3 | 0.950 |
| N2—C14 | 1.411 (4) | C4—H4 | 0.950 |
| C1—C2 | 1.384 (4) | C5—H5 | 0.950 |
| C1—C5 | 1.379 (5) | C7—H7A | 0.990 |
| C1—C6 | 1.497 (5) | C7—H7B | 0.990 |
| C2—C3 | 1.386 (5) | C12—H12A | 0.990 |
| C4—C5 | 1.384 (5) | C12—H12B | 0.990 |
| C7—C8 | 1.469 (4) | C15—H15 | 0.950 |
| C8—C9 | 1.194 (4) | C16—H16 | 0.950 |
| C9—C10 | 1.382 (4) | C17—H17 | 0.950 |
| C10—C11 | 1.202 (4) | C18—H18 | 0.950 |
| C11—C12 | 1.458 (4) | C19—H19 | 0.950 |
| O1···C2 | 2.839 (4) | C13···H12Bv | 3.4943 |
| O1···C7 | 2.676 (4) | C13···H15i | 3.5175 |
| O1···C8 | 3.072 (4) | C13···H16i | 3.4255 |
| O2···C5 | 2.758 (5) | C14···H5viii | 3.4640 |
| O2···C9 | 3.504 (4) | C14···H7Aiii | 2.9551 |
| O3···C10 | 3.463 (4) | C14···H16i | 3.3284 |
| O3···C14 | 3.587 (4) | C14···H17i | 3.4854 |
| O4···C11 | 2.988 (4) | C15···H1iv | 3.36 (4) |
| O4···C12 | 2.643 (4) | C15···H5viii | 3.1008 |
| O4···C14 | 2.935 (4) | C15···H7Aiii | 3.5026 |
| O4···C15 | 2.887 (4) | C16···H1iv | 3.09 (3) |
| N1···C1 | 2.805 (5) | C16···H5viii | 2.7844 |
| N2···C12 | 3.533 (4) | C17···H1iv | 3.27 (3) |
| C2···C4 | 2.700 (5) | C17···H4viii | 3.1952 |
| C3···C5 | 2.708 (5) | C17···H5viii | 2.8713 |
| C6···C8 | 3.053 (4) | C17···H19iv | 3.2787 |
| C11···C13 | 2.974 (4) | C18···H2iii | 3.4707 |
| C13···C15 | 3.002 (4) | C18···H3xii | 3.1872 |
| C14···C17 | 2.789 (4) | C18···H4viii | 3.0448 |
| C15···C18 | 2.782 (5) | C18···H4xiii | 3.5611 |
| C16···C19 | 2.764 (5) | C18···H5viii | 3.2312 |
| O1···O2i | 3.442 (3) | C19···H3xii | 3.4449 |
| O1···O3ii | 3.336 (4) | C19···H5viii | 3.5009 |
| O1···N2ii | 2.963 (4) | C19···H7Aiii | 3.4775 |
| O1···C18iii | 3.567 (4) | C19···H17i | 3.1548 |
| O1···C19iii | 3.486 (4) | H1···O1ii | 2.10 (4) |
| O2···O1iv | 3.442 (3) | H1···O2iii | 3.55 (4) |
| O3···O1ii | 3.336 (4) | H1···C6ii | 3.25 (4) |
| O3···C7ii | 3.288 (5) | H1···C7iii | 3.38 (3) |
| O3···C8ii | 3.241 (4) | H1···C15i | 3.36 (4) |
| O3···C15i | 3.412 (4) | H1···C16i | 3.09 (3) |
| O4···C11v | 3.079 (5) | H1···C17i | 3.27 (3) |
| O4···C12v | 2.986 (5) | H1···H7Aiii | 3.0191 |
| N1···C2vi | 3.534 (4) | H1···H7Aii | 3.1087 |
| N2···O1ii | 2.963 (4) | H1···H7Biii | 3.1052 |
| N2···C7iii | 3.358 (5) | H1···H16i | 3.3461 |
| N2···C15i | 3.584 (4) | H2···N1vii | 2.9295 |
| N2···C16i | 3.170 (4) | H2···C3vii | 3.0544 |
| N2···C17i | 3.529 (4) | H2···C5i | 3.3478 |
| C2···N1vii | 3.534 (4) | H2···C18iii | 3.4707 |
| C3···C3vi | 3.547 (5) | H2···H3vi | 3.3599 |
| C3···C3vii | 3.547 (5) | H2···H3vii | 2.9048 |
| C6···C19iii | 3.393 (5) | H2···H5i | 3.2944 |
| C7···O3ii | 3.288 (5) | H2···H18iii | 3.0691 |
| C7···N2iii | 3.358 (5) | H2···H19ii | 2.7610 |
| C8···O3ii | 3.241 (4) | H3···N1vii | 3.1052 |
| C11···O4viii | 3.079 (5) | H3···C1vii | 3.3187 |
| C12···O4viii | 2.986 (5) | H3···C2vii | 2.9631 |
| C13···C15i | 3.597 (5) | H3···C3vii | 2.8278 |
| C13···C16i | 3.552 (4) | H3···C4i | 3.5399 |
| C14···C16i | 3.552 (5) | H3···C4vii | 3.3957 |
| C15···O3iv | 3.412 (4) | H3···C5vii | 3.5233 |
| C15···N2iv | 3.584 (4) | H3···C18xi | 3.1872 |
| C15···C13iv | 3.597 (5) | H3···C19xi | 3.4449 |
| C16···N2iv | 3.170 (4) | H3···H2vi | 2.9048 |
| C16···C13iv | 3.552 (4) | H3···H2vii | 3.3599 |
| C16···C14iv | 3.552 (5) | H3···H3vi | 3.1387 |
| C17···N2iv | 3.529 (4) | H3···H3vii | 3.1387 |
| C17···C19iv | 3.522 (5) | H3···H4i | 3.3367 |
| C18···O1iii | 3.567 (4) | H3···H18xi | 2.4257 |
| C19···O1iii | 3.486 (4) | H3···H19xi | 2.9620 |
| C19···C6iii | 3.393 (5) | H4···N1ix | 3.5641 |
| C19···C17i | 3.522 (5) | H4···C3iv | 3.4002 |
| O1···H2 | 2.5617 | H4···C17v | 3.1952 |
| O1···H7A | 2.4752 | H4···C18v | 3.0448 |
| O2···H5 | 2.4652 | H4···C18x | 3.5611 |
| O3···H1 | 2.18 (4) | H4···H3iv | 3.3367 |
| O4···H1 | 2.99 (4) | H4···H4xiv | 3.2416 |
| O4···H12A | 3.5975 | H4···H17v | 3.2166 |
| O4···H12B | 2.4401 | H4···H17viii | 3.3174 |
| O4···H15 | 2.2759 | H4···H17x | 3.4430 |
| N1···H2 | 3.2559 | H4···H18v | 2.9488 |
| N1···H5 | 3.2535 | H4···H18x | 2.7665 |
| N2···H15 | 2.6797 | H5···C2iv | 3.4796 |
| N2···H19 | 2.5440 | H5···C14v | 3.4640 |
| C1···H3 | 3.2338 | H5···C15v | 3.1008 |
| C1···H4 | 3.2237 | H5···C16v | 2.7844 |
| C2···H5 | 3.2399 | H5···C17v | 2.8713 |
| C3···H4 | 3.1312 | H5···C18v | 3.2312 |
| C4···H3 | 3.1321 | H5···C19v | 3.5009 |
| C5···H2 | 3.2386 | H5···H2iv | 3.2944 |
| C6···H2 | 2.6280 | H5···H15v | 3.5748 |
| C6···H5 | 2.7181 | H5···H16v | 3.1138 |
| C6···H7A | 2.5065 | H5···H16viii | 3.3297 |
| C6···H7B | 3.1662 | H5···H17v | 3.2551 |
| C9···H7A | 3.1189 | H5···H17viii | 3.1088 |
| C9···H7B | 3.1208 | H7A···O3ii | 2.5279 |
| C10···H12A | 3.1345 | H7A···O4iii | 3.5739 |
| C10···H12B | 3.1260 | H7A···N2iii | 2.7606 |
| C13···H12A | 3.1814 | H7A···C12ii | 3.2314 |
| C13···H12B | 2.5129 | H7A···C13iii | 3.1164 |
| C13···H15 | 2.7518 | H7A···C14iii | 2.9551 |
| C14···H16 | 3.2532 | H7A···C15iii | 3.5026 |
| C14···H18 | 3.2728 | H7A···C19iii | 3.4775 |
| C15···H1 | 3.25 (4) | H7A···H1iii | 3.0191 |
| C15···H17 | 3.2706 | H7A···H1ii | 3.1087 |
| C15···H19 | 3.2687 | H7A···H12Aii | 2.8769 |
| C16···H18 | 3.2496 | H7B···O1iv | 3.3719 |
| C17···H15 | 3.2695 | H7B···O3iii | 3.2920 |
| C17···H19 | 3.2612 | H7B···N2iii | 3.2132 |
| C18···H16 | 3.2472 | H7B···C8iv | 3.3574 |
| C19···H1 | 2.54 (3) | H7B···C9iv | 2.9517 |
| C19···H15 | 3.2725 | H7B···C10iv | 3.0341 |
| C19···H17 | 3.2637 | H7B···C11iv | 3.5607 |
| H1···H15 | 3.5459 | H7B···C13iii | 3.3533 |
| H1···H19 | 2.3512 | H7B···H1iii | 3.1052 |
| H2···H3 | 2.3166 | H7B···H12Aii | 3.5210 |
| H4···H5 | 2.3111 | H7B···H15v | 3.5820 |
| H15···H16 | 2.3319 | H12A···O4i | 3.1541 |
| H16···H17 | 2.3300 | H12A···O4viii | 2.9963 |
| H17···H18 | 2.3398 | H12A···C7ii | 3.4077 |
| H18···H19 | 2.3333 | H12A···C8i | 3.5855 |
| O1···H1ii | 2.10 (4) | H12A···C8ii | 3.2925 |
| O1···H7Bi | 3.3719 | H12A···C9i | 3.0384 |
| O1···H16viii | 3.4101 | H12A···C10i | 2.9445 |
| O1···H19ii | 2.9853 | H12A···C11i | 3.3701 |
| O2···H1iii | 3.55 (4) | H12A···H7Aii | 2.8769 |
| O2···H16viii | 3.0338 | H12A···H7Bii | 3.5210 |
| O2···H19iii | 3.4623 | H12A···H12Bviii | 2.9679 |
| O3···H7Aii | 2.5279 | H12B···O4i | 3.4323 |
| O3···H7Biii | 3.2920 | H12B···O4viii | 2.4733 |
| O3···H15i | 3.2742 | H12B···C10viii | 3.0332 |
| O4···H7Aiii | 3.5739 | H12B···C11viii | 2.8967 |
| O4···H12Aiv | 3.1541 | H12B···C12v | 3.4043 |
| O4···H12Av | 2.9963 | H12B···C12viii | 3.3431 |
| O4···H12Biv | 3.4323 | H12B···C13viii | 3.4943 |
| O4···H12Bv | 2.4733 | H12B···H12Av | 2.9679 |
| N1···H2vi | 2.9295 | H12B···H12Bv | 2.9006 |
| N1···H3vi | 3.1052 | H12B···H12Bviii | 2.9006 |
| N1···H4ix | 3.5641 | H12B···H15i | 3.4367 |
| N1···H17viii | 3.4548 | H15···O3iv | 3.2742 |
| N1···H17x | 3.3395 | H15···C9v | 3.3711 |
| N1···H18x | 3.0693 | H15···C10v | 3.1513 |
| N1···H18xi | 3.1776 | H15···C11v | 3.4195 |
| N1···H19xi | 3.2327 | H15···C13iv | 3.5175 |
| N2···H7Aiii | 2.7606 | H15···H5viii | 3.5748 |
| N2···H7Biii | 3.2132 | H15···H7Bviii | 3.5820 |
| N2···H16i | 3.1631 | H15···H12Biv | 3.4367 |
| C1···H3vi | 3.3187 | H16···O1v | 3.4101 |
| C1···H16viii | 3.1868 | H16···O2v | 3.0338 |
| C1···H17viii | 3.1857 | H16···N2iv | 3.1631 |
| C1···H19iii | 3.4819 | H16···C1v | 3.1868 |
| C2···H3vi | 2.9631 | H16···C5v | 3.4000 |
| C2···H5i | 3.4796 | H16···C6v | 2.9449 |
| C2···H17viii | 3.5935 | H16···C8v | 3.3030 |
| C2···H18iii | 3.3262 | H16···C9v | 3.4629 |
| C3···H2vi | 3.0544 | H16···C13iv | 3.4255 |
| C3···H3vi | 2.8278 | H16···C14iv | 3.3284 |
| C3···H4i | 3.4002 | H16···H1iv | 3.3461 |
| C3···H18xi | 2.9823 | H16···H5v | 3.3297 |
| C3···H19xi | 3.4811 | H16···H5viii | 3.1138 |
| C4···H3iv | 3.5399 | H17···N1v | 3.4548 |
| C4···H3vi | 3.3957 | H17···N1xiii | 3.3395 |
| C4···H17viii | 2.9945 | H17···C1v | 3.1857 |
| C4···H18x | 3.1953 | H17···C2v | 3.5935 |
| C5···H2iv | 3.3478 | H17···C4v | 2.9945 |
| C5···H3vi | 3.5233 | H17···C5v | 2.8503 |
| C5···H16viii | 3.4000 | H17···C14iv | 3.4854 |
| C5···H17viii | 2.8503 | H17···C19iv | 3.1548 |
| C6···H1ii | 3.25 (4) | H17···H4v | 3.3174 |
| C6···H16viii | 2.9449 | H17···H4viii | 3.2166 |
| C6···H19iii | 3.3088 | H17···H4xiii | 3.4430 |
| C7···H1iii | 3.38 (3) | H17···H5v | 3.1088 |
| C7···H12Aii | 3.4077 | H17···H5viii | 3.2551 |
| C8···H7Bi | 3.3574 | H17···H19iv | 3.0338 |
| C8···H12Aiv | 3.5855 | H18···N1xiii | 3.0693 |
| C8···H12Aii | 3.2925 | H18···N1xii | 3.1776 |
| C8···H16viii | 3.3030 | H18···C2iii | 3.3262 |
| C9···H7Bi | 2.9517 | H18···C3xii | 2.9823 |
| C9···H12Aiv | 3.0384 | H18···C4xiii | 3.1953 |
| C9···H15viii | 3.3711 | H18···H2iii | 3.0691 |
| C9···H16viii | 3.4629 | H18···H3xii | 2.4257 |
| C10···H7Bi | 3.0341 | H18···H4viii | 2.9488 |
| C10···H12Aiv | 2.9445 | H18···H4xiii | 2.7665 |
| C10···H12Bv | 3.0332 | H19···O1ii | 2.9853 |
| C10···H15viii | 3.1513 | H19···O2iii | 3.4623 |
| C11···H7Bi | 3.5607 | H19···N1xii | 3.2327 |
| C11···H12Aiv | 3.3701 | H19···C1iii | 3.4819 |
| C11···H12Bv | 2.8967 | H19···C3xii | 3.4811 |
| C11···H15viii | 3.4195 | H19···C6iii | 3.3088 |
| C12···H7Aii | 3.2314 | H19···C17i | 3.2787 |
| C12···H12Bv | 3.3431 | H19···H2ii | 2.7610 |
| C12···H12Bviii | 3.4043 | H19···H3xii | 2.9620 |
| C13···H7Aiii | 3.1164 | H19···H17i | 3.0338 |
| C13···H7Biii | 3.3533 | ||
| C6—O2—C7 | 116.2 (3) | C13—N2—H1 | 112 (2) |
| C12—O3—C13 | 114.2 (3) | C14—N2—H1 | 121 (2) |
| C3—N1—C4 | 115.8 (3) | C1—C2—H2 | 120.575 |
| C13—N2—C14 | 127.1 (3) | C3—C2—H2 | 120.580 |
| C2—C1—C5 | 118.4 (3) | N1—C3—H3 | 118.068 |
| C2—C1—C6 | 118.5 (3) | C2—C3—H3 | 118.070 |
| C5—C1—C6 | 123.2 (3) | N1—C4—H4 | 117.750 |
| C1—C2—C3 | 118.8 (3) | C5—C4—H4 | 117.738 |
| N1—C3—C2 | 123.9 (3) | C1—C5—H5 | 120.684 |
| N1—C4—C5 | 124.5 (3) | C4—C5—H5 | 120.689 |
| C1—C5—C4 | 118.6 (3) | O2—C7—H7A | 109.100 |
| O1—C6—O2 | 124.3 (3) | O2—C7—H7B | 109.089 |
| O1—C6—C1 | 123.7 (3) | C8—C7—H7A | 109.096 |
| O2—C6—C1 | 111.9 (3) | C8—C7—H7B | 109.097 |
| O2—C7—C8 | 112.5 (3) | H7A—C7—H7B | 107.850 |
| C7—C8—C9 | 177.3 (4) | O3—C12—H12A | 109.237 |
| C8—C9—C10 | 178.7 (4) | O3—C12—H12B | 109.235 |
| C9—C10—C11 | 179.2 (4) | C11—C12—H12A | 109.250 |
| C10—C11—C12 | 179.1 (3) | C11—C12—H12B | 109.249 |
| O3—C12—C11 | 111.9 (3) | H12A—C12—H12B | 107.930 |
| O3—C13—O4 | 123.5 (3) | C14—C15—H15 | 120.265 |
| O3—C13—N2 | 109.3 (3) | C16—C15—H15 | 120.251 |
| O4—C13—N2 | 127.2 (3) | C15—C16—H16 | 119.381 |
| N2—C14—C15 | 124.0 (3) | C17—C16—H16 | 119.385 |
| N2—C14—C19 | 116.5 (3) | C16—C17—H17 | 120.336 |
| C15—C14—C19 | 119.6 (3) | C18—C17—H17 | 120.363 |
| C14—C15—C16 | 119.5 (3) | C17—C18—H18 | 119.850 |
| C15—C16—C17 | 121.2 (3) | C19—C18—H18 | 119.841 |
| C16—C17—C18 | 119.3 (3) | C14—C19—H19 | 119.963 |
| C17—C18—C19 | 120.3 (4) | C18—C19—H19 | 119.966 |
| C14—C19—C18 | 120.1 (3) | ||
| C6—O2—C7—C8 | 77.1 (3) | C2—C1—C6—O2 | −172.6 (3) |
| C7—O2—C6—O1 | −3.2 (4) | C6—C1—C2—C3 | −179.6 (2) |
| C7—O2—C6—C1 | 177.4 (2) | C5—C1—C6—O1 | −170.8 (3) |
| C12—O3—C13—O4 | −4.3 (4) | C5—C1—C6—O2 | 8.5 (4) |
| C12—O3—C13—N2 | 176.2 (2) | C6—C1—C5—C4 | 178.9 (3) |
| C13—O3—C12—C11 | −72.4 (3) | C1—C2—C3—N1 | 1.2 (5) |
| C3—N1—C4—C5 | 0.2 (5) | N1—C4—C5—C1 | 0.2 (5) |
| C4—N1—C3—C2 | −0.9 (5) | N2—C14—C15—C16 | 177.0 (2) |
| C13—N2—C14—C15 | −1.4 (5) | N2—C14—C19—C18 | −176.9 (2) |
| C13—N2—C14—C19 | 177.9 (3) | C15—C14—C19—C18 | 2.4 (4) |
| C14—N2—C13—O3 | −179.5 (3) | C19—C14—C15—C16 | −2.3 (4) |
| C14—N2—C13—O4 | 1.0 (5) | C14—C15—C16—C17 | 0.7 (4) |
| C2—C1—C5—C4 | 0.1 (4) | C15—C16—C17—C18 | 0.8 (4) |
| C5—C1—C2—C3 | −0.7 (4) | C16—C17—C18—C19 | −0.6 (5) |
| C2—C1—C6—O1 | 8.1 (5) | C17—C18—C19—C14 | −1.0 (5) |
| Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y, −z+2; (iv) x, y−1, z; (v) −x+1, y−1/2, −z+3/2; (vi) −x+2, y−1/2, −z+5/2; (vii) −x+2, y+1/2, −z+5/2; (viii) −x+1, y+1/2, −z+3/2; (ix) −x+2, −y, −z+2; (x) x+1, −y−1/2, z+1/2; (xi) x+1, −y+1/2, z+1/2; (xii) x−1, −y+1/2, z−1/2; (xiii) x−1, −y−1/2, z−1/2; (xiv) −x+2, −y−1, −z+2. |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H1···O1ii | 0.88 (4) | 2.10 (4) | 2.963 (4) | 165 (3) |
| Symmetry code: (ii) −x+1, −y+1, −z+2. |
Stacking parameters of the diacetylenes in both polymorphs. top
| Parametersa | Limitation | Polymorph I | Polymorph II |
| d (Å) | 4.5–5.6 | 4.354 (3) | 5.160 (2) |
| θ(°) | 40–50 | 61.5 | 47.6 |
| r (Å) | <4.0 | 4.18 | 3.82 |
| Note: (a) parameters are defined in Fig. 1. |
