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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161787
https://doi.org/10.1107/S2414314616017879

3-(9H-Carbazol-9-yl)propanoic acid

CROSSMARK_Color_square_no_text.svg
Manpreet Kaur,a Shaaban K. Mohamed,b,c Mehmet Akkurt,d Jerry P. Jasinski,a Talaat I. El-Emarye and Mustafa R. Albayatif*

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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 30 October 2016; accepted 8 November 2016; online 10 November 2016)

The title compound, C15H13NO2, crystallizes with two mol­ecules (A and B) in the asymmetric unit. 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.

CCDC reference: 1515591

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

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[Kumara Swamy, K. C., Bhuvan Kumar, N. N., Balaraman, E. & Pavan Kumar, K. V. P. (2009). Chem. Rev. 109, 2551-2651.]; Broadbent et al., 1998[Broadbent, A., Thomas, H. & Broadbent, S. (1998). Curr. Med. Chem. 5, 469-491.]; Xia et al., 2008[Xia, Y., Fan, C.-D., Zhao, B.-X., Zhao, J., Shin, D.-S. & Miao, J.-Y. (2008). Eur. J. Med. Chem. 43, 2347-2353.]). As part of our studies in this area, we herein report the synthesis and crystal structure of the title compound.

As shown in Fig. 1[link], there are two mol­ecules (A and B) in the asymmetric unit: 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[Akkurt, M., Jasinski, J. P., Mohamed, S. K., El-Emary, T. I. & Albayati, M. R. (2015). Acta Cryst. E71, o937-o938.]; Fun et al., 2010[Fun, H.-K., Goh, J. H., Asiri, A. M., Khan, S. A. & Khan, K. A. (2010). Acta Cryst. E66, o1200-o1201.]; Archana et al., 2010[Archana, R., Prabakaran, K., Rajendra Prasad, K. J., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o3146.]).

[Figure 1]
Figure 1
The title compound with 50% probability displacement ellipsoids.

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[link], Table 1[link]). The three-dimensional architecture is consolidated by C—H⋯π inter­actions (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

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.
[Figure 2]
Figure 2
A view of the dimers in the unit cell with the hydrogen bonds shown by dotted lines.

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 chromatography (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 refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C15H13NO2
Mr 239.26
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 173
a, b, c (Å) 9.4550 (5), 11.9077 (6), 12.2120 (7)
α, β, γ (°) 62.429 (5), 79.276 (4), 77.627 (4)
V (Å3) 1184.47 (12)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.72
Crystal size (mm) 0.38 × 0.24 × 0.02
 
Data collection
Diffractometer Rigaku Oxford Diffraction Eos Gemini
Absorption correction Multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.])
Tmin, Tmax 0.804, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 8217, 4490, 3605
Rint 0.041
(sin θ/λ)max (Å−1) 0.615
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.125, 1.03
No. of reflections 4490
No. of parameters 327
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.23, −0.25
Computer programs: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data

CCDC reference: 1515591

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017879/hb4092sup1.cif

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

checkCIF report


Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: 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).

3-(9H-Carbazol-9-yl)propanoic acid top
Crystal data top
C15H13NO2Z = 4
Mr = 239.26F(000) = 504
Triclinic, P1Dx = 1.342 Mg m−3
a = 9.4550 (5) ÅCu Kα radiation, λ = 1.54184 Å
b = 11.9077 (6) ÅCell parameters from 3450 reflections
c = 12.2120 (7) Åθ = 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) Å30.38 × 0.24 × 0.02 mm
Data collection top
Rigaku Oxford Diffraction Eos Gemini
diffractometer		4490 independent reflections
Radiation source: Enhance (Cu) X-ray Source3605 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 16.0416 pixels mm-1θmax = 71.4°, θmin = 4.1°
ω scansh = −8→11
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)		k = −14→13
Tmin = 0.804, Tmax = 1.000l = −14→14
8217 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-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 reflectionsΔρmax = 0.23 e Å−3
327 parametersΔρmin = −0.25 e Å−3
0 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.30384 (13)0.53906 (11)0.50496 (11)0.0368 (3)
H1A0.37280.48700.54400.055*
O2A0.48660 (13)0.63144 (11)0.36956 (11)0.0363 (3)
N1A0.34738 (14)0.92232 (12)0.18471 (12)0.0276 (3)
C1A0.35653 (17)0.62751 (14)0.40047 (14)0.0280 (3)
C2A0.24026 (17)0.72309 (14)0.32348 (15)0.0295 (3)
H2AA0.18850.77610.36570.035*
H2AB0.16880.67660.31790.035*
C3A0.29874 (18)0.81094 (14)0.19250 (15)0.0296 (3)
H3AA0.38120.76150.16290.035*
H3AB0.22140.84010.13650.035*
C4A0.48895 (17)0.94769 (14)0.16488 (14)0.0269 (3)
C5A0.62051 (19)0.87355 (16)0.15129 (15)0.0334 (4)
H5A0.62340.79090.15670.040*
C6A0.74688 (19)0.92506 (17)0.12951 (16)0.0380 (4)
H6A0.83800.87690.11900.046*
C7A0.74389 (19)1.04588 (17)0.12266 (16)0.0379 (4)
H7A0.83271.07800.10800.045*
C8A0.61415 (18)1.11927 (15)0.13675 (15)0.0320 (4)
H8A0.61291.20110.13280.038*
C9A0.48409 (17)1.07082 (14)0.15706 (14)0.0266 (3)
C10A0.33290 (17)1.12215 (14)0.17007 (13)0.0268 (3)
C11A0.25935 (18)1.23829 (15)0.16644 (15)0.0318 (4)
H11A0.31191.30320.15520.038*
C12A0.10905 (19)1.25785 (16)0.17948 (16)0.0356 (4)
H12A0.05801.33680.17690.043*
C13A0.03124 (18)1.16260 (16)0.19641 (16)0.0347 (4)
H13A−0.07211.17800.20560.042*
C14A0.10125 (18)1.04660 (15)0.20008 (15)0.0307 (3)
H14A0.04790.98220.21150.037*
C15A0.25248 (17)1.02766 (14)0.18644 (14)0.0264 (3)
O1B0.19516 (14)−0.03589 (12)0.49393 (13)0.0418 (3)
H1B0.1181−0.05960.49290.063*
O2B0.03890 (13)0.12573 (11)0.51304 (12)0.0386 (3)
N1B0.29252 (14)0.34102 (12)0.39404 (12)0.0280 (3)
C1B0.16291 (19)0.06936 (14)0.50979 (14)0.0316 (4)
C2B0.2935 (2)0.10816 (16)0.52860 (17)0.0379 (4)
H2BA0.37360.10270.46540.046*
H2BB0.32490.04570.61110.046*
C3B0.27139 (19)0.24259 (16)0.52076 (15)0.0337 (4)
H3BA0.17160.26130.55690.040*
H3BB0.34070.24520.57090.040*
C4B0.42766 (17)0.36444 (15)0.32828 (15)0.0289 (3)
C5B0.56543 (18)0.30203 (17)0.36535 (17)0.0352 (4)
H5B0.57710.23030.44390.042*
C6B0.68471 (19)0.34902 (19)0.28274 (19)0.0408 (4)
H6B0.77990.30920.30590.049*
C7B0.6682 (2)0.4534 (2)0.16639 (18)0.0423 (4)
H7B0.75210.48310.11190.051*
C8B0.53203 (19)0.51376 (17)0.12957 (17)0.0356 (4)
H8B0.52160.58430.05010.043*
C9B0.40870 (17)0.46945 (15)0.21127 (14)0.0276 (3)
C10B0.25444 (17)0.51095 (14)0.20579 (14)0.0261 (3)
C11B0.16898 (19)0.60655 (15)0.11495 (15)0.0318 (4)
H11B0.21290.65870.03550.038*
C12B0.01968 (19)0.62424 (16)0.14224 (16)0.0350 (4)
H12B−0.03940.68850.08080.042*
C13B−0.04531 (18)0.54809 (16)0.25991 (17)0.0348 (4)
H13B−0.14770.56400.27780.042*
C14B0.03629 (18)0.45028 (15)0.35055 (15)0.0312 (3)
H14B−0.00850.39800.42960.037*
C15B0.18638 (17)0.43128 (14)0.32170 (14)0.0261 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0351 (6)0.0327 (6)0.0308 (6)−0.0078 (5)0.0006 (5)−0.0045 (5)
O2A0.0340 (6)0.0307 (6)0.0326 (6)−0.0066 (5)0.0002 (5)−0.0046 (5)
N1A0.0292 (7)0.0200 (6)0.0321 (7)−0.0023 (5)−0.0034 (5)−0.0107 (5)
C1A0.0345 (8)0.0225 (7)0.0280 (7)−0.0073 (6)0.0019 (6)−0.0125 (6)
C2A0.0340 (8)0.0211 (7)0.0348 (8)−0.0053 (6)−0.0007 (6)−0.0140 (6)
C3A0.0383 (9)0.0215 (7)0.0298 (8)−0.0044 (6)−0.0057 (6)−0.0112 (6)
C4A0.0304 (8)0.0225 (7)0.0225 (7)−0.0036 (6)−0.0023 (6)−0.0056 (6)
C5A0.0365 (9)0.0259 (7)0.0301 (8)0.0000 (6)−0.0014 (6)−0.0086 (6)
C6A0.0306 (8)0.0379 (9)0.0322 (8)0.0020 (7)−0.0019 (6)−0.0077 (7)
C7A0.0318 (8)0.0391 (9)0.0335 (9)−0.0090 (7)−0.0041 (7)−0.0063 (7)
C8A0.0357 (9)0.0277 (8)0.0279 (8)−0.0094 (6)−0.0038 (6)−0.0061 (6)
C9A0.0302 (8)0.0232 (7)0.0230 (7)−0.0048 (6)−0.0030 (6)−0.0068 (6)
C10A0.0330 (8)0.0223 (7)0.0225 (7)−0.0047 (6)−0.0022 (6)−0.0077 (6)
C11A0.0393 (9)0.0248 (7)0.0333 (8)−0.0063 (6)−0.0018 (7)−0.0144 (7)
C12A0.0401 (9)0.0278 (8)0.0394 (9)0.0037 (7)−0.0042 (7)−0.0190 (7)
C13A0.0293 (8)0.0346 (8)0.0383 (9)0.0012 (7)−0.0037 (7)−0.0167 (7)
C14A0.0317 (8)0.0266 (7)0.0329 (8)−0.0058 (6)−0.0032 (6)−0.0115 (6)
C15A0.0312 (8)0.0209 (7)0.0243 (7)−0.0032 (6)−0.0037 (6)−0.0076 (6)
O1B0.0383 (7)0.0310 (6)0.0559 (8)−0.0018 (5)−0.0064 (6)−0.0197 (6)
O2B0.0364 (7)0.0296 (6)0.0469 (7)−0.0071 (5)0.0021 (5)−0.0158 (5)
N1B0.0298 (7)0.0238 (6)0.0275 (7)−0.0063 (5)0.0000 (5)−0.0088 (5)
C1B0.0395 (9)0.0207 (7)0.0251 (7)−0.0059 (6)0.0003 (6)−0.0029 (6)
C2B0.0405 (9)0.0264 (8)0.0346 (9)−0.0059 (7)−0.0073 (7)−0.0016 (7)
C3B0.0406 (9)0.0320 (8)0.0257 (8)−0.0101 (7)−0.0022 (6)−0.0087 (7)
C4B0.0307 (8)0.0273 (7)0.0336 (8)−0.0074 (6)0.0014 (6)−0.0179 (7)
C5B0.0348 (9)0.0350 (9)0.0406 (9)−0.0034 (7)−0.0049 (7)−0.0210 (8)
C6B0.0285 (8)0.0511 (11)0.0543 (11)−0.0040 (7)−0.0025 (8)−0.0343 (9)
C7B0.0330 (9)0.0562 (11)0.0492 (11)−0.0169 (8)0.0106 (8)−0.0340 (10)
C8B0.0367 (9)0.0392 (9)0.0355 (9)−0.0155 (7)0.0083 (7)−0.0205 (7)
C9B0.0325 (8)0.0261 (7)0.0300 (8)−0.0096 (6)0.0021 (6)−0.0168 (6)
C10B0.0311 (8)0.0219 (7)0.0280 (7)−0.0084 (6)0.0027 (6)−0.0135 (6)
C11B0.0411 (9)0.0228 (7)0.0284 (8)−0.0077 (6)0.0009 (6)−0.0089 (6)
C12B0.0391 (9)0.0264 (8)0.0356 (9)−0.0005 (6)−0.0060 (7)−0.0114 (7)
C13B0.0287 (8)0.0348 (8)0.0417 (9)−0.0033 (6)0.0004 (7)−0.0195 (7)
C14B0.0317 (8)0.0285 (8)0.0316 (8)−0.0109 (6)0.0042 (6)−0.0118 (7)
C15B0.0320 (8)0.0197 (7)0.0277 (7)−0.0057 (6)−0.0003 (6)−0.0116 (6)
Geometric parameters (Å, º) top
O1A—H1A0.8400O1B—H1B0.8400
O1A—C1A1.3153 (19)O1B—C1B1.319 (2)
O2A—C1A1.222 (2)O2B—C1B1.224 (2)
N1A—C3A1.4520 (19)N1B—C3B1.4541 (19)
N1A—C4A1.388 (2)N1B—C4B1.385 (2)
N1A—C15A1.384 (2)N1B—C15B1.390 (2)
C1A—C2A1.499 (2)C1B—C2B1.496 (2)
C2A—H2AA0.9900C2B—H2BA0.9900
C2A—H2AB0.9900C2B—H2BB0.9900
C2A—C3A1.526 (2)C2B—C3B1.529 (2)
C3A—H3AA0.9900C3B—H3BA0.9900
C3A—H3AB0.9900C3B—H3BB0.9900
C4A—C5A1.394 (2)C4B—C5B1.395 (2)
C4A—C9A1.416 (2)C4B—C9B1.408 (2)
C5A—H5A0.9500C5B—H5B0.9500
C5A—C6A1.385 (3)C5B—C6B1.388 (3)
C6A—H6A0.9500C6B—H6B0.9500
C6A—C7A1.396 (3)C6B—C7B1.397 (3)
C7A—H7A0.9500C7B—H7B0.9500
C7A—C8A1.378 (2)C7B—C8B1.377 (3)
C8A—H8A0.9500C8B—H8B0.9500
C8A—C9A1.402 (2)C8B—C9B1.406 (2)
C9A—C10A1.440 (2)C9B—C10B1.440 (2)
C10A—C11A1.393 (2)C10B—C11B1.396 (2)
C10A—C15A1.409 (2)C10B—C15B1.413 (2)
C11A—H11A0.9500C11B—H11B0.9500
C11A—C12A1.381 (2)C11B—C12B1.382 (2)
C12A—H12A0.9500C12B—H12B0.9500
C12A—C13A1.398 (2)C12B—C13B1.403 (2)
C13A—H13A0.9500C13B—H13B0.9500
C13A—C14A1.382 (2)C13B—C14B1.384 (2)
C14A—H14A0.9500C14B—H14B0.9500
C14A—C15A1.390 (2)C14B—C15B1.393 (2)
C1A—O1A—H1A109.5C1B—O1B—H1B109.5
C4A—N1A—C3A128.09 (13)C4B—N1B—C3B123.93 (14)
C15A—N1A—C3A122.96 (13)C4B—N1B—C15B108.55 (13)
C15A—N1A—C4A108.76 (13)C15B—N1B—C3B127.40 (13)
O1A—C1A—C2A112.92 (14)O1B—C1B—C2B112.47 (15)
O2A—C1A—O1A123.53 (15)O2B—C1B—O1B123.31 (16)
O2A—C1A—C2A123.56 (14)O2B—C1B—C2B124.17 (16)
C1A—C2A—H2AA108.9C1B—C2B—H2BA108.4
C1A—C2A—H2AB108.9C1B—C2B—H2BB108.4
C1A—C2A—C3A113.39 (13)C1B—C2B—C3B115.39 (14)
H2AA—C2A—H2AB107.7H2BA—C2B—H2BB107.5
C3A—C2A—H2AA108.9C3B—C2B—H2BA108.4
C3A—C2A—H2AB108.9C3B—C2B—H2BB108.4
N1A—C3A—C2A113.38 (13)N1B—C3B—C2B112.67 (14)
N1A—C3A—H3AA108.9N1B—C3B—H3BA109.1
N1A—C3A—H3AB108.9N1B—C3B—H3BB109.1
C2A—C3A—H3AA108.9C2B—C3B—H3BA109.1
C2A—C3A—H3AB108.9C2B—C3B—H3BB109.1
H3AA—C3A—H3AB107.7H3BA—C3B—H3BB107.8
N1A—C4A—C5A130.03 (15)N1B—C4B—C5B128.97 (16)
N1A—C4A—C9A108.48 (13)N1B—C4B—C9B109.05 (14)
C5A—C4A—C9A121.49 (14)C5B—C4B—C9B121.96 (15)
C4A—C5A—H5A121.3C4B—C5B—H5B121.4
C6A—C5A—C4A117.43 (16)C6B—C5B—C4B117.28 (17)
C6A—C5A—H5A121.3C6B—C5B—H5B121.4
C5A—C6A—H6A119.1C5B—C6B—H6B119.2
C5A—C6A—C7A121.74 (16)C5B—C6B—C7B121.65 (17)
C7A—C6A—H6A119.1C7B—C6B—H6B119.2
C6A—C7A—H7A119.5C6B—C7B—H7B119.6
C8A—C7A—C6A121.07 (16)C8B—C7B—C6B120.88 (16)
C8A—C7A—H7A119.5C8B—C7B—H7B119.6
C7A—C8A—H8A120.7C7B—C8B—H8B120.5
C7A—C8A—C9A118.67 (16)C7B—C8B—C9B119.04 (17)
C9A—C8A—H8A120.7C9B—C8B—H8B120.5
C4A—C9A—C10A107.01 (13)C4B—C9B—C10B106.91 (13)
C8A—C9A—C4A119.60 (15)C8B—C9B—C4B119.18 (16)
C8A—C9A—C10A133.36 (15)C8B—C9B—C10B133.87 (16)
C11A—C10A—C9A134.19 (15)C11B—C10B—C9B133.98 (14)
C11A—C10A—C15A119.35 (15)C11B—C10B—C15B119.44 (14)
C15A—C10A—C9A106.44 (13)C15B—C10B—C9B106.57 (14)
C10A—C11A—H11A120.4C10B—C11B—H11B120.5
C12A—C11A—C10A119.10 (15)C12B—C11B—C10B119.09 (15)
C12A—C11A—H11A120.4C12B—C11B—H11B120.5
C11A—C12A—H12A119.7C11B—C12B—H12B119.7
C11A—C12A—C13A120.68 (15)C11B—C12B—C13B120.57 (16)
C13A—C12A—H12A119.7C13B—C12B—H12B119.7
C12A—C13A—H13A119.3C12B—C13B—H13B119.2
C14A—C13A—C12A121.50 (16)C14B—C13B—C12B121.56 (15)
C14A—C13A—H13A119.3C14B—C13B—H13B119.2
C13A—C14A—H14A121.2C13B—C14B—H14B121.2
C13A—C14A—C15A117.56 (15)C13B—C14B—C15B117.58 (15)
C15A—C14A—H14A121.2C15B—C14B—H14B121.2
N1A—C15A—C10A109.29 (14)N1B—C15B—C10B108.86 (13)
N1A—C15A—C14A128.90 (15)N1B—C15B—C14B129.49 (14)
C14A—C15A—C10A121.81 (15)C14B—C15B—C10B121.63 (14)
O1A—C1A—C2A—C3A−169.33 (13)O1B—C1B—C2B—C3B167.86 (14)
O2A—C1A—C2A—C3A10.8 (2)O2B—C1B—C2B—C3B−14.6 (2)
N1A—C4A—C5A—C6A178.64 (16)N1B—C4B—C5B—C6B−176.93 (16)
N1A—C4A—C9A—C8A−179.81 (14)N1B—C4B—C9B—C8B177.79 (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—C5B0.9 (3)
C3A—N1A—C4A—C9A176.60 (14)C3B—N1B—C4B—C9B−177.33 (14)
C3A—N1A—C15A—C10A−176.56 (13)C3B—N1B—C15B—C10B178.26 (14)
C3A—N1A—C15A—C14A2.7 (2)C3B—N1B—C15B—C14B−0.3 (3)
C4A—N1A—C3A—C2A108.94 (17)C4B—N1B—C3B—C2B−76.71 (19)
C4A—N1A—C15A—C10A−1.21 (17)C4B—N1B—C15B—C10B2.18 (17)
C4A—N1A—C15A—C14A178.09 (16)C4B—N1B—C15B—C14B−176.35 (16)
C4A—C5A—C6A—C7A0.7 (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—C15A0.56 (16)C4B—C9B—C10B—C15B1.69 (17)
C5A—C4A—C9A—C8A−0.8 (2)C5B—C4B—C9B—C8B−0.6 (2)
C5A—C4A—C9A—C10A177.70 (14)C5B—C4B—C9B—C10B−178.80 (15)
C5A—C6A—C7A—C8A−0.3 (3)C5B—C6B—C7B—C8B0.1 (3)
C6A—C7A—C8A—C9A−0.6 (2)C6B—C7B—C8B—C9B0.4 (3)
C7A—C8A—C9A—C4A1.2 (2)C7B—C8B—C9B—C4B−0.2 (2)
C7A—C8A—C9A—C10A−176.89 (16)C7B—C8B—C9B—C10B177.41 (17)
C8A—C9A—C10A—C11A0.6 (3)C8B—C9B—C10B—C11B3.9 (3)
C8A—C9A—C10A—C15A178.78 (17)C8B—C9B—C10B—C15B−176.11 (17)
C9A—C4A—C5A—C6A−0.1 (2)C9B—C4B—C5B—C6B1.1 (2)
C9A—C10A—C11A—C12A178.20 (16)C9B—C10B—C11B—C12B−177.64 (17)
C9A—C10A—C15A—N1A0.39 (17)C9B—C10B—C15B—N1B−2.39 (17)
C9A—C10A—C15A—C14A−178.98 (14)C9B—C10B—C15B—C14B176.28 (14)
C10A—C11A—C12A—C13A0.2 (3)C10B—C11B—C12B—C13B0.6 (3)
C11A—C10A—C15A—N1A178.85 (13)C11B—C10B—C15B—N1B177.58 (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—C15A0.1 (3)C12B—C13B—C14B—C15B1.1 (3)
C13A—C14A—C15A—N1A−178.88 (15)C13B—C14B—C15B—N1B−179.69 (16)
C13A—C14A—C15A—C10A0.3 (2)C13B—C14B—C15B—C10B1.9 (2)
C15A—N1A—C3A—C2A−76.66 (18)C15B—N1B—C3B—C2B107.77 (18)
C15A—N1A—C4A—C5A−177.33 (15)C15B—N1B—C4B—C5B177.16 (16)
C15A—N1A—C4A—C9A1.56 (17)C15B—N1B—C4B—C9B−1.09 (17)
C15A—C10A—C11A—C12A0.2 (2)C15B—C10B—C11B—C12B2.4 (2)
Hydrogen-bond geometry (Å, º) top
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···AD—HH···AD···AD—H···A
O1A—H1A···O2Ai0.841.792.6310 (17)177
O1B—H1B···O2Bii0.841.852.6867 (18)174
C2A—H2AB···Cg90.992.643.5319 (19)150
C2B—H2BB···Cg2i0.992.943.805 (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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ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161787
https://doi.org/10.1107/S2414314616017879
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