organic compounds
3-(9H-Carbazol-9-yl)propanoic acid
aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eDepartment of Chemistry, Faculty of Science, Assiut University, 71515 Assiut, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
The title compound, C15H13NO2, crystallizes with two molecules (A and B) in the The carbazole ring systems of both molecules are close to planar (r.m.s deviations = 0.035 and 0.053 Å). In the crystal, A+A and B+B inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R22(8) loops and weak C—H⋯π interactions link the dimers into a three-dimensional network.
Keywords: crystal structure; carbazole ring system; hydrogen bonds; dimer.
CCDC reference: 1515591
Structure description
Compounds based on carbazole ring systems have been reported to exhibit diverse biological activities such as cytotoxic, antitumor, antiviral, antimicrobial, antiparasitics, antiserotonin and anti-inflammatory activities (e.g.: Kumara Swamy et al., 2009; Broadbent et al., 1998; Xia et al., 2008). As part of our studies in this area, we herein report the synthesis and of the title compound.
As shown in Fig. 1, there are two molecules (A and B) in the the carbazole ring systems of both molecules are close to planar (r.m.s deviation = 0.035 and 0.053 Å). The bond-length distributions within the molecules A and B of the title compound are almost identical. These values are in good agreement with those observed in related structures (Akkurt et al., 2015; Fun et al., 2010; Archana et al., 2010).
In the crystal, pairwise O—H⋯O hydrogen bonds link pairs of molecules into A+A and B+B inversion dimers with R22(8) ring motifs (Fig. 2, Table 1). The three-dimensional architecture is consolidated by C—H⋯π interactions (Table 1).
Synthesis and crystallization
The title compound was obtained as an unexpected product of the reaction of 9,9a-dihydro-4aH-carbazole (0.01 mol, 1.69 g) with an excess of ethyl 3-chloropropanoate (0.1 mol, 13.7 g) in the presence of potassium carbonate under reflux for 3 h. The intended product was the corresponding ethyl ester, {ethyl 3-[4aH-carbazol-9(9aH)-yl]propanoate}. We assume that the ester has been hydrolysed under the basic reaction conditions employed into the corresponding carboxylic acid (title compound). The title compound was isolated by plate-layer (PLC) then the extracted product was dissolved in dimethylsulfoxide and left to evaporate slowly at room temperature to give colourless plates. The purity of the product was confirmed by TLC using ethyl acetate:cyclohexane (10: 1) as the mobile phase.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1515591
https://doi.org/10.1107/S2414314616017879/hb4092sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017879/hb4092Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616017879/hb4092Isup3.cml
Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C15H13NO2 | Z = 4 |
Mr = 239.26 | F(000) = 504 |
Triclinic, P1 | Dx = 1.342 Mg m−3 |
a = 9.4550 (5) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 11.9077 (6) Å | Cell parameters from 3450 reflections |
c = 12.2120 (7) Å | θ = 4.1–71.2° |
α = 62.429 (5)° | µ = 0.72 mm−1 |
β = 79.276 (4)° | T = 173 K |
γ = 77.627 (4)° | Plate, colourless |
V = 1184.47 (12) Å3 | 0.38 × 0.24 × 0.02 mm |
Rigaku Oxford Diffraction Eos Gemini diffractometer | 4490 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3605 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 71.4°, θmin = 4.1° |
ω scans | h = −8→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −14→13 |
Tmin = 0.804, Tmax = 1.000 | l = −14→14 |
8217 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.070P)2 + 0.1104P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4490 reflections | Δρmax = 0.23 e Å−3 |
327 parameters | Δρmin = −0.25 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.30384 (13) | 0.53906 (11) | 0.50496 (11) | 0.0368 (3) | |
H1A | 0.3728 | 0.4870 | 0.5440 | 0.055* | |
O2A | 0.48660 (13) | 0.63144 (11) | 0.36956 (11) | 0.0363 (3) | |
N1A | 0.34738 (14) | 0.92232 (12) | 0.18471 (12) | 0.0276 (3) | |
C1A | 0.35653 (17) | 0.62751 (14) | 0.40047 (14) | 0.0280 (3) | |
C2A | 0.24026 (17) | 0.72309 (14) | 0.32348 (15) | 0.0295 (3) | |
H2AA | 0.1885 | 0.7761 | 0.3657 | 0.035* | |
H2AB | 0.1688 | 0.6766 | 0.3179 | 0.035* | |
C3A | 0.29874 (18) | 0.81094 (14) | 0.19250 (15) | 0.0296 (3) | |
H3AA | 0.3812 | 0.7615 | 0.1629 | 0.035* | |
H3AB | 0.2214 | 0.8401 | 0.1365 | 0.035* | |
C4A | 0.48895 (17) | 0.94769 (14) | 0.16488 (14) | 0.0269 (3) | |
C5A | 0.62051 (19) | 0.87355 (16) | 0.15129 (15) | 0.0334 (4) | |
H5A | 0.6234 | 0.7909 | 0.1567 | 0.040* | |
C6A | 0.74688 (19) | 0.92506 (17) | 0.12951 (16) | 0.0380 (4) | |
H6A | 0.8380 | 0.8769 | 0.1190 | 0.046* | |
C7A | 0.74389 (19) | 1.04588 (17) | 0.12266 (16) | 0.0379 (4) | |
H7A | 0.8327 | 1.0780 | 0.1080 | 0.045* | |
C8A | 0.61415 (18) | 1.11927 (15) | 0.13675 (15) | 0.0320 (4) | |
H8A | 0.6129 | 1.2011 | 0.1328 | 0.038* | |
C9A | 0.48409 (17) | 1.07082 (14) | 0.15706 (14) | 0.0266 (3) | |
C10A | 0.33290 (17) | 1.12215 (14) | 0.17007 (13) | 0.0268 (3) | |
C11A | 0.25935 (18) | 1.23829 (15) | 0.16644 (15) | 0.0318 (4) | |
H11A | 0.3119 | 1.3032 | 0.1552 | 0.038* | |
C12A | 0.10905 (19) | 1.25785 (16) | 0.17948 (16) | 0.0356 (4) | |
H12A | 0.0580 | 1.3368 | 0.1769 | 0.043* | |
C13A | 0.03124 (18) | 1.16260 (16) | 0.19641 (16) | 0.0347 (4) | |
H13A | −0.0721 | 1.1780 | 0.2056 | 0.042* | |
C14A | 0.10125 (18) | 1.04660 (15) | 0.20008 (15) | 0.0307 (3) | |
H14A | 0.0479 | 0.9822 | 0.2115 | 0.037* | |
C15A | 0.25248 (17) | 1.02766 (14) | 0.18644 (14) | 0.0264 (3) | |
O1B | 0.19516 (14) | −0.03589 (12) | 0.49393 (13) | 0.0418 (3) | |
H1B | 0.1181 | −0.0596 | 0.4929 | 0.063* | |
O2B | 0.03890 (13) | 0.12573 (11) | 0.51304 (12) | 0.0386 (3) | |
N1B | 0.29252 (14) | 0.34102 (12) | 0.39404 (12) | 0.0280 (3) | |
C1B | 0.16291 (19) | 0.06936 (14) | 0.50979 (14) | 0.0316 (4) | |
C2B | 0.2935 (2) | 0.10816 (16) | 0.52860 (17) | 0.0379 (4) | |
H2BA | 0.3736 | 0.1027 | 0.4654 | 0.046* | |
H2BB | 0.3249 | 0.0457 | 0.6111 | 0.046* | |
C3B | 0.27139 (19) | 0.24259 (16) | 0.52076 (15) | 0.0337 (4) | |
H3BA | 0.1716 | 0.2613 | 0.5569 | 0.040* | |
H3BB | 0.3407 | 0.2452 | 0.5709 | 0.040* | |
C4B | 0.42766 (17) | 0.36444 (15) | 0.32828 (15) | 0.0289 (3) | |
C5B | 0.56543 (18) | 0.30203 (17) | 0.36535 (17) | 0.0352 (4) | |
H5B | 0.5771 | 0.2303 | 0.4439 | 0.042* | |
C6B | 0.68471 (19) | 0.34902 (19) | 0.28274 (19) | 0.0408 (4) | |
H6B | 0.7799 | 0.3092 | 0.3059 | 0.049* | |
C7B | 0.6682 (2) | 0.4534 (2) | 0.16639 (18) | 0.0423 (4) | |
H7B | 0.7521 | 0.4831 | 0.1119 | 0.051* | |
C8B | 0.53203 (19) | 0.51376 (17) | 0.12957 (17) | 0.0356 (4) | |
H8B | 0.5216 | 0.5843 | 0.0501 | 0.043* | |
C9B | 0.40870 (17) | 0.46945 (15) | 0.21127 (14) | 0.0276 (3) | |
C10B | 0.25444 (17) | 0.51095 (14) | 0.20579 (14) | 0.0261 (3) | |
C11B | 0.16898 (19) | 0.60655 (15) | 0.11495 (15) | 0.0318 (4) | |
H11B | 0.2129 | 0.6587 | 0.0355 | 0.038* | |
C12B | 0.01968 (19) | 0.62424 (16) | 0.14224 (16) | 0.0350 (4) | |
H12B | −0.0394 | 0.6885 | 0.0808 | 0.042* | |
C13B | −0.04531 (18) | 0.54809 (16) | 0.25991 (17) | 0.0348 (4) | |
H13B | −0.1477 | 0.5640 | 0.2778 | 0.042* | |
C14B | 0.03629 (18) | 0.45028 (15) | 0.35055 (15) | 0.0312 (3) | |
H14B | −0.0085 | 0.3980 | 0.4296 | 0.037* | |
C15B | 0.18638 (17) | 0.43128 (14) | 0.32170 (14) | 0.0261 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0351 (6) | 0.0327 (6) | 0.0308 (6) | −0.0078 (5) | 0.0006 (5) | −0.0045 (5) |
O2A | 0.0340 (6) | 0.0307 (6) | 0.0326 (6) | −0.0066 (5) | 0.0002 (5) | −0.0046 (5) |
N1A | 0.0292 (7) | 0.0200 (6) | 0.0321 (7) | −0.0023 (5) | −0.0034 (5) | −0.0107 (5) |
C1A | 0.0345 (8) | 0.0225 (7) | 0.0280 (7) | −0.0073 (6) | 0.0019 (6) | −0.0125 (6) |
C2A | 0.0340 (8) | 0.0211 (7) | 0.0348 (8) | −0.0053 (6) | −0.0007 (6) | −0.0140 (6) |
C3A | 0.0383 (9) | 0.0215 (7) | 0.0298 (8) | −0.0044 (6) | −0.0057 (6) | −0.0112 (6) |
C4A | 0.0304 (8) | 0.0225 (7) | 0.0225 (7) | −0.0036 (6) | −0.0023 (6) | −0.0056 (6) |
C5A | 0.0365 (9) | 0.0259 (7) | 0.0301 (8) | 0.0000 (6) | −0.0014 (6) | −0.0086 (6) |
C6A | 0.0306 (8) | 0.0379 (9) | 0.0322 (8) | 0.0020 (7) | −0.0019 (6) | −0.0077 (7) |
C7A | 0.0318 (8) | 0.0391 (9) | 0.0335 (9) | −0.0090 (7) | −0.0041 (7) | −0.0063 (7) |
C8A | 0.0357 (9) | 0.0277 (8) | 0.0279 (8) | −0.0094 (6) | −0.0038 (6) | −0.0061 (6) |
C9A | 0.0302 (8) | 0.0232 (7) | 0.0230 (7) | −0.0048 (6) | −0.0030 (6) | −0.0068 (6) |
C10A | 0.0330 (8) | 0.0223 (7) | 0.0225 (7) | −0.0047 (6) | −0.0022 (6) | −0.0077 (6) |
C11A | 0.0393 (9) | 0.0248 (7) | 0.0333 (8) | −0.0063 (6) | −0.0018 (7) | −0.0144 (7) |
C12A | 0.0401 (9) | 0.0278 (8) | 0.0394 (9) | 0.0037 (7) | −0.0042 (7) | −0.0190 (7) |
C13A | 0.0293 (8) | 0.0346 (8) | 0.0383 (9) | 0.0012 (7) | −0.0037 (7) | −0.0167 (7) |
C14A | 0.0317 (8) | 0.0266 (7) | 0.0329 (8) | −0.0058 (6) | −0.0032 (6) | −0.0115 (6) |
C15A | 0.0312 (8) | 0.0209 (7) | 0.0243 (7) | −0.0032 (6) | −0.0037 (6) | −0.0076 (6) |
O1B | 0.0383 (7) | 0.0310 (6) | 0.0559 (8) | −0.0018 (5) | −0.0064 (6) | −0.0197 (6) |
O2B | 0.0364 (7) | 0.0296 (6) | 0.0469 (7) | −0.0071 (5) | 0.0021 (5) | −0.0158 (5) |
N1B | 0.0298 (7) | 0.0238 (6) | 0.0275 (7) | −0.0063 (5) | 0.0000 (5) | −0.0088 (5) |
C1B | 0.0395 (9) | 0.0207 (7) | 0.0251 (7) | −0.0059 (6) | 0.0003 (6) | −0.0029 (6) |
C2B | 0.0405 (9) | 0.0264 (8) | 0.0346 (9) | −0.0059 (7) | −0.0073 (7) | −0.0016 (7) |
C3B | 0.0406 (9) | 0.0320 (8) | 0.0257 (8) | −0.0101 (7) | −0.0022 (6) | −0.0087 (7) |
C4B | 0.0307 (8) | 0.0273 (7) | 0.0336 (8) | −0.0074 (6) | 0.0014 (6) | −0.0179 (7) |
C5B | 0.0348 (9) | 0.0350 (9) | 0.0406 (9) | −0.0034 (7) | −0.0049 (7) | −0.0210 (8) |
C6B | 0.0285 (8) | 0.0511 (11) | 0.0543 (11) | −0.0040 (7) | −0.0025 (8) | −0.0343 (9) |
C7B | 0.0330 (9) | 0.0562 (11) | 0.0492 (11) | −0.0169 (8) | 0.0106 (8) | −0.0340 (10) |
C8B | 0.0367 (9) | 0.0392 (9) | 0.0355 (9) | −0.0155 (7) | 0.0083 (7) | −0.0205 (7) |
C9B | 0.0325 (8) | 0.0261 (7) | 0.0300 (8) | −0.0096 (6) | 0.0021 (6) | −0.0168 (6) |
C10B | 0.0311 (8) | 0.0219 (7) | 0.0280 (7) | −0.0084 (6) | 0.0027 (6) | −0.0135 (6) |
C11B | 0.0411 (9) | 0.0228 (7) | 0.0284 (8) | −0.0077 (6) | 0.0009 (6) | −0.0089 (6) |
C12B | 0.0391 (9) | 0.0264 (8) | 0.0356 (9) | −0.0005 (6) | −0.0060 (7) | −0.0114 (7) |
C13B | 0.0287 (8) | 0.0348 (8) | 0.0417 (9) | −0.0033 (6) | 0.0004 (7) | −0.0195 (7) |
C14B | 0.0317 (8) | 0.0285 (8) | 0.0316 (8) | −0.0109 (6) | 0.0042 (6) | −0.0118 (7) |
C15B | 0.0320 (8) | 0.0197 (7) | 0.0277 (7) | −0.0057 (6) | −0.0003 (6) | −0.0116 (6) |
O1A—H1A | 0.8400 | O1B—H1B | 0.8400 |
O1A—C1A | 1.3153 (19) | O1B—C1B | 1.319 (2) |
O2A—C1A | 1.222 (2) | O2B—C1B | 1.224 (2) |
N1A—C3A | 1.4520 (19) | N1B—C3B | 1.4541 (19) |
N1A—C4A | 1.388 (2) | N1B—C4B | 1.385 (2) |
N1A—C15A | 1.384 (2) | N1B—C15B | 1.390 (2) |
C1A—C2A | 1.499 (2) | C1B—C2B | 1.496 (2) |
C2A—H2AA | 0.9900 | C2B—H2BA | 0.9900 |
C2A—H2AB | 0.9900 | C2B—H2BB | 0.9900 |
C2A—C3A | 1.526 (2) | C2B—C3B | 1.529 (2) |
C3A—H3AA | 0.9900 | C3B—H3BA | 0.9900 |
C3A—H3AB | 0.9900 | C3B—H3BB | 0.9900 |
C4A—C5A | 1.394 (2) | C4B—C5B | 1.395 (2) |
C4A—C9A | 1.416 (2) | C4B—C9B | 1.408 (2) |
C5A—H5A | 0.9500 | C5B—H5B | 0.9500 |
C5A—C6A | 1.385 (3) | C5B—C6B | 1.388 (3) |
C6A—H6A | 0.9500 | C6B—H6B | 0.9500 |
C6A—C7A | 1.396 (3) | C6B—C7B | 1.397 (3) |
C7A—H7A | 0.9500 | C7B—H7B | 0.9500 |
C7A—C8A | 1.378 (2) | C7B—C8B | 1.377 (3) |
C8A—H8A | 0.9500 | C8B—H8B | 0.9500 |
C8A—C9A | 1.402 (2) | C8B—C9B | 1.406 (2) |
C9A—C10A | 1.440 (2) | C9B—C10B | 1.440 (2) |
C10A—C11A | 1.393 (2) | C10B—C11B | 1.396 (2) |
C10A—C15A | 1.409 (2) | C10B—C15B | 1.413 (2) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C11A—C12A | 1.381 (2) | C11B—C12B | 1.382 (2) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C12A—C13A | 1.398 (2) | C12B—C13B | 1.403 (2) |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
C13A—C14A | 1.382 (2) | C13B—C14B | 1.384 (2) |
C14A—H14A | 0.9500 | C14B—H14B | 0.9500 |
C14A—C15A | 1.390 (2) | C14B—C15B | 1.393 (2) |
C1A—O1A—H1A | 109.5 | C1B—O1B—H1B | 109.5 |
C4A—N1A—C3A | 128.09 (13) | C4B—N1B—C3B | 123.93 (14) |
C15A—N1A—C3A | 122.96 (13) | C4B—N1B—C15B | 108.55 (13) |
C15A—N1A—C4A | 108.76 (13) | C15B—N1B—C3B | 127.40 (13) |
O1A—C1A—C2A | 112.92 (14) | O1B—C1B—C2B | 112.47 (15) |
O2A—C1A—O1A | 123.53 (15) | O2B—C1B—O1B | 123.31 (16) |
O2A—C1A—C2A | 123.56 (14) | O2B—C1B—C2B | 124.17 (16) |
C1A—C2A—H2AA | 108.9 | C1B—C2B—H2BA | 108.4 |
C1A—C2A—H2AB | 108.9 | C1B—C2B—H2BB | 108.4 |
C1A—C2A—C3A | 113.39 (13) | C1B—C2B—C3B | 115.39 (14) |
H2AA—C2A—H2AB | 107.7 | H2BA—C2B—H2BB | 107.5 |
C3A—C2A—H2AA | 108.9 | C3B—C2B—H2BA | 108.4 |
C3A—C2A—H2AB | 108.9 | C3B—C2B—H2BB | 108.4 |
N1A—C3A—C2A | 113.38 (13) | N1B—C3B—C2B | 112.67 (14) |
N1A—C3A—H3AA | 108.9 | N1B—C3B—H3BA | 109.1 |
N1A—C3A—H3AB | 108.9 | N1B—C3B—H3BB | 109.1 |
C2A—C3A—H3AA | 108.9 | C2B—C3B—H3BA | 109.1 |
C2A—C3A—H3AB | 108.9 | C2B—C3B—H3BB | 109.1 |
H3AA—C3A—H3AB | 107.7 | H3BA—C3B—H3BB | 107.8 |
N1A—C4A—C5A | 130.03 (15) | N1B—C4B—C5B | 128.97 (16) |
N1A—C4A—C9A | 108.48 (13) | N1B—C4B—C9B | 109.05 (14) |
C5A—C4A—C9A | 121.49 (14) | C5B—C4B—C9B | 121.96 (15) |
C4A—C5A—H5A | 121.3 | C4B—C5B—H5B | 121.4 |
C6A—C5A—C4A | 117.43 (16) | C6B—C5B—C4B | 117.28 (17) |
C6A—C5A—H5A | 121.3 | C6B—C5B—H5B | 121.4 |
C5A—C6A—H6A | 119.1 | C5B—C6B—H6B | 119.2 |
C5A—C6A—C7A | 121.74 (16) | C5B—C6B—C7B | 121.65 (17) |
C7A—C6A—H6A | 119.1 | C7B—C6B—H6B | 119.2 |
C6A—C7A—H7A | 119.5 | C6B—C7B—H7B | 119.6 |
C8A—C7A—C6A | 121.07 (16) | C8B—C7B—C6B | 120.88 (16) |
C8A—C7A—H7A | 119.5 | C8B—C7B—H7B | 119.6 |
C7A—C8A—H8A | 120.7 | C7B—C8B—H8B | 120.5 |
C7A—C8A—C9A | 118.67 (16) | C7B—C8B—C9B | 119.04 (17) |
C9A—C8A—H8A | 120.7 | C9B—C8B—H8B | 120.5 |
C4A—C9A—C10A | 107.01 (13) | C4B—C9B—C10B | 106.91 (13) |
C8A—C9A—C4A | 119.60 (15) | C8B—C9B—C4B | 119.18 (16) |
C8A—C9A—C10A | 133.36 (15) | C8B—C9B—C10B | 133.87 (16) |
C11A—C10A—C9A | 134.19 (15) | C11B—C10B—C9B | 133.98 (14) |
C11A—C10A—C15A | 119.35 (15) | C11B—C10B—C15B | 119.44 (14) |
C15A—C10A—C9A | 106.44 (13) | C15B—C10B—C9B | 106.57 (14) |
C10A—C11A—H11A | 120.4 | C10B—C11B—H11B | 120.5 |
C12A—C11A—C10A | 119.10 (15) | C12B—C11B—C10B | 119.09 (15) |
C12A—C11A—H11A | 120.4 | C12B—C11B—H11B | 120.5 |
C11A—C12A—H12A | 119.7 | C11B—C12B—H12B | 119.7 |
C11A—C12A—C13A | 120.68 (15) | C11B—C12B—C13B | 120.57 (16) |
C13A—C12A—H12A | 119.7 | C13B—C12B—H12B | 119.7 |
C12A—C13A—H13A | 119.3 | C12B—C13B—H13B | 119.2 |
C14A—C13A—C12A | 121.50 (16) | C14B—C13B—C12B | 121.56 (15) |
C14A—C13A—H13A | 119.3 | C14B—C13B—H13B | 119.2 |
C13A—C14A—H14A | 121.2 | C13B—C14B—H14B | 121.2 |
C13A—C14A—C15A | 117.56 (15) | C13B—C14B—C15B | 117.58 (15) |
C15A—C14A—H14A | 121.2 | C15B—C14B—H14B | 121.2 |
N1A—C15A—C10A | 109.29 (14) | N1B—C15B—C10B | 108.86 (13) |
N1A—C15A—C14A | 128.90 (15) | N1B—C15B—C14B | 129.49 (14) |
C14A—C15A—C10A | 121.81 (15) | C14B—C15B—C10B | 121.63 (14) |
O1A—C1A—C2A—C3A | −169.33 (13) | O1B—C1B—C2B—C3B | 167.86 (14) |
O2A—C1A—C2A—C3A | 10.8 (2) | O2B—C1B—C2B—C3B | −14.6 (2) |
N1A—C4A—C5A—C6A | 178.64 (16) | N1B—C4B—C5B—C6B | −176.93 (16) |
N1A—C4A—C9A—C8A | −179.81 (14) | N1B—C4B—C9B—C8B | 177.79 (14) |
N1A—C4A—C9A—C10A | −1.30 (16) | N1B—C4B—C9B—C10B | −0.40 (17) |
C1A—C2A—C3A—N1A | −85.68 (17) | C1B—C2B—C3B—N1B | −85.25 (18) |
C3A—N1A—C4A—C5A | −2.3 (3) | C3B—N1B—C4B—C5B | 0.9 (3) |
C3A—N1A—C4A—C9A | 176.60 (14) | C3B—N1B—C4B—C9B | −177.33 (14) |
C3A—N1A—C15A—C10A | −176.56 (13) | C3B—N1B—C15B—C10B | 178.26 (14) |
C3A—N1A—C15A—C14A | 2.7 (2) | C3B—N1B—C15B—C14B | −0.3 (3) |
C4A—N1A—C3A—C2A | 108.94 (17) | C4B—N1B—C3B—C2B | −76.71 (19) |
C4A—N1A—C15A—C10A | −1.21 (17) | C4B—N1B—C15B—C10B | 2.18 (17) |
C4A—N1A—C15A—C14A | 178.09 (16) | C4B—N1B—C15B—C14B | −176.35 (16) |
C4A—C5A—C6A—C7A | 0.7 (3) | C4B—C5B—C6B—C7B | −0.9 (3) |
C4A—C9A—C10A—C11A | −177.58 (17) | C4B—C9B—C10B—C11B | −178.26 (17) |
C4A—C9A—C10A—C15A | 0.56 (16) | C4B—C9B—C10B—C15B | 1.69 (17) |
C5A—C4A—C9A—C8A | −0.8 (2) | C5B—C4B—C9B—C8B | −0.6 (2) |
C5A—C4A—C9A—C10A | 177.70 (14) | C5B—C4B—C9B—C10B | −178.80 (15) |
C5A—C6A—C7A—C8A | −0.3 (3) | C5B—C6B—C7B—C8B | 0.1 (3) |
C6A—C7A—C8A—C9A | −0.6 (2) | C6B—C7B—C8B—C9B | 0.4 (3) |
C7A—C8A—C9A—C4A | 1.2 (2) | C7B—C8B—C9B—C4B | −0.2 (2) |
C7A—C8A—C9A—C10A | −176.89 (16) | C7B—C8B—C9B—C10B | 177.41 (17) |
C8A—C9A—C10A—C11A | 0.6 (3) | C8B—C9B—C10B—C11B | 3.9 (3) |
C8A—C9A—C10A—C15A | 178.78 (17) | C8B—C9B—C10B—C15B | −176.11 (17) |
C9A—C4A—C5A—C6A | −0.1 (2) | C9B—C4B—C5B—C6B | 1.1 (2) |
C9A—C10A—C11A—C12A | 178.20 (16) | C9B—C10B—C11B—C12B | −177.64 (17) |
C9A—C10A—C15A—N1A | 0.39 (17) | C9B—C10B—C15B—N1B | −2.39 (17) |
C9A—C10A—C15A—C14A | −178.98 (14) | C9B—C10B—C15B—C14B | 176.28 (14) |
C10A—C11A—C12A—C13A | 0.2 (3) | C10B—C11B—C12B—C13B | 0.6 (3) |
C11A—C10A—C15A—N1A | 178.85 (13) | C11B—C10B—C15B—N1B | 177.58 (14) |
C11A—C10A—C15A—C14A | −0.5 (2) | C11B—C10B—C15B—C14B | −3.8 (2) |
C11A—C12A—C13A—C14A | −0.3 (3) | C11B—C12B—C13B—C14B | −2.4 (3) |
C12A—C13A—C14A—C15A | 0.1 (3) | C12B—C13B—C14B—C15B | 1.1 (3) |
C13A—C14A—C15A—N1A | −178.88 (15) | C13B—C14B—C15B—N1B | −179.69 (16) |
C13A—C14A—C15A—C10A | 0.3 (2) | C13B—C14B—C15B—C10B | 1.9 (2) |
C15A—N1A—C3A—C2A | −76.66 (18) | C15B—N1B—C3B—C2B | 107.77 (18) |
C15A—N1A—C4A—C5A | −177.33 (15) | C15B—N1B—C4B—C5B | 177.16 (16) |
C15A—N1A—C4A—C9A | 1.56 (17) | C15B—N1B—C4B—C9B | −1.09 (17) |
C15A—C10A—C11A—C12A | 0.2 (2) | C15B—C10B—C11B—C12B | 2.4 (2) |
Cg2 and Cg9 are the centroids of the C4A–C9A ring of molecule A, and the C10B–C15B ring of molecule B, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2Ai | 0.84 | 1.79 | 2.6310 (17) | 177 |
O1B—H1B···O2Bii | 0.84 | 1.85 | 2.6867 (18) | 174 |
C2A—H2AB···Cg9 | 0.99 | 2.64 | 3.5319 (19) | 150 |
C2B—H2BB···Cg2i | 0.99 | 2.94 | 3.805 (2) | 147 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1. |
Acknowledgements
JPJ thanks the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X ray diffractometer.
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