organic compounds
2,7-Dibromo-10′H-spiro[fluorene-9,9′-phenanthren]-10′-one
aDepartment of Chemistry Tunghai University No. 1727, Sec. 4, Taiwan Boulevard, Xitun District, Taichung 40704, Taiwan, bInternational Institute for Carbon-Neutral Energy Research (I2CNER), Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan, and cInstitute of Chemistry, Academia Sinica, 115 Taipei, Taiwan
*Correspondence e-mail: mwata@i2cner.kyushu-u.ac.jp, jaychang@thu.edu.tw
The title racemic spiro compound, C26H14Br2O, crystallizes with two independent molecules (A and B) in the The mean plane of the phenanthrene unit is twisted with respect to the mean plane of the fluorene unit by 82.38 (15) and 80.25 (5)° in molecules A and B, respectively. In the crystal, the A and B molecules are linked by a pair of C—H⋯O hydrogen bonds and a pair of short Br⋯O contacts [2.935 (2) Å], forming a centrosymmetric four-molecule unit. These units are linked by C—H⋯π interactions, forming ribbons propagating along the b-axis direction. The ribbons are linked by C—Br⋯π interactions, forming layers parallel to the ab plane.
Keywords: crystal structure; spiro; brominated derivative; fluorene; phenanthrene; C—H⋯O hydrogen bonds; short Br⋯O contact; C—H⋯π interactions; C—Br⋯π interactions.
CCDC reference: 1534283
Structure description
The parent structure, 10′H-spiro[fluorene-9,9′-phenanthren]-10′-one and its analogues have been studied for the reactivity of fluorene (Suzuki et al. 1962). They are also of interest as building blocks for the preparation of microporous materials (Taylor et al. 2016) and for their electro-chemical properties (Debroy et al. 2007). Synthetic methods and physical properties of brominated 10′H-spiro[fluorene-9,9′-phenanthren]-10′-one compounds have been reported (Suzuki et al., 1962; Borowitz et al., 1971). Herein, we report on the high-yield synthesis and the of the title racemic spiro compound, which to the best of our knowledge is a unique example of this type of compound.
The title compound, illustrated in Fig. 1, crystallizes with two independent molecules (A and B) in the In molecule A, the mean plane of the fluorene unit (r.m.s. deviation = 0.02 Å) is inclined to the mean plane of the phenanthrene unit (r.m.s. deviation = 0.096 Å) by 82.38 (5)°. In molecule B, the corresponding angle is 80.25 (5)° (r.m.s. deviations are 0.02 and 0.123 Å, respectively), indicating that the conformation of the two molecules is very similar.
In the crystal, the A and B molecules are linked by a pair of C—H⋯O hydrogen bonds and a pair of short Br⋯O contacts [2.935 (2) Å], forming a centrosymmetric four-molecule unit (Table 1 and Fig. 2). These units are linked by C—H⋯π interactions, forming ribbons along the b axis direction (Table 1 and Fig. 3). The ribbons are linked by C—Br⋯π interactions, forming layers parallel to the ab plane (Table 1 and Fig. 4).
Synthesis and crystallization
The title compound was synthesized from the reaction of 10′H-spiro[fluorene-9,9′-phenanthren]-10′-one (1 mg, 2.9 mmol) and bromine (0.4 ml, 7.76 mmol) in dichloromethane at room temperature (86% yield). Colourless plate-like crystals of the title compound were grown by slow evaporation, at room temperature, of a solution in dichloromethane (m.p. 533–535 K). 1H (400 MHz, CDCl3): δ 8.22 (d, 1H, J = 8.12 Hz), 8.14 (d, 1H, J = 7.8 Hz), 8.03 (dd, 1H, J = 7.76, 1.32 Hz), 7.84 (t, 1H, J = 7.92 Hz), 7.66 (s, 1H), 7.64 (s, 1H), 7.49–7.55 (m, 3H), 7.43 (t, 1H, J = 7.86 Hz), 7.13–7.17 (m, 3H), 6.59 (dd, 1H, J = 7.88, 1.12 Hz). 13C (100 MHz, CDCl3): δ 195.7, 149.1, 139.6, 137.7, 137.5, 135.4, 131.7, 130.3, 129.5, 129.3, 128.8, 128.7, 128.6, 128.2, 127.9, 124.3, 123.4, 121.9, 121.8.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1534283
https://doi.org/10.1107/S2414314617003017/su5344sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617003017/su5344Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617003017/su5344Isup3.cml
Data collection: APEX2 (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).C26H14Br2O | F(000) = 1984 |
Mr = 502.19 | Dx = 1.691 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.511 (1) Å | Cell parameters from 9798 reflections |
b = 8.9191 (7) Å | θ = 2.7–27.1° |
c = 25.2761 (15) Å | µ = 4.13 mm−1 |
β = 92.179 (2)° | T = 100 K |
V = 3944.8 (4) Å3 | Prism, colourless |
Z = 8 | 0.44 × 0.30 × 0.26 mm |
Bruker APEXII CCD diffractometer | 7162 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.072 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 27.1°, θmin = 2.0° |
Tmin = 0.640, Tmax = 0.971 | h = −22→22 |
122604 measured reflections | k = −11→11 |
8667 independent reflections | l = −32→32 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0228P)2 + 4.6257P] where P = (Fo2 + 2Fc2)/3 |
8667 reflections | (Δ/σ)max = 0.002 |
523 parameters | Δρmax = 1.46 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
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 | ||
Br1 | 0.58632 (2) | 0.45391 (3) | 0.53916 (2) | 0.01768 (6) | |
Br2 | 1.17959 (2) | 0.52190 (3) | 0.62371 (2) | 0.02688 (7) | |
O1 | 0.88959 (10) | 0.17311 (18) | 0.55147 (6) | 0.0196 (4) | |
C1 | 0.87687 (13) | 0.3717 (2) | 0.61400 (9) | 0.0135 (5) | |
C2 | 0.89106 (13) | 0.2074 (2) | 0.59816 (9) | 0.0140 (5) | |
C3 | 0.91023 (12) | 0.0977 (3) | 0.64026 (9) | 0.0139 (5) | |
C4 | 0.93583 (13) | −0.0449 (3) | 0.62497 (10) | 0.0178 (5) | |
H4 | 0.9399 | −0.0677 | 0.5885 | 0.021* | |
C5 | 0.95512 (15) | −0.1518 (3) | 0.66266 (10) | 0.0239 (6) | |
H5 | 0.9726 | −0.2479 | 0.6523 | 0.029* | |
C6 | 0.94871 (16) | −0.1173 (3) | 0.71570 (11) | 0.0288 (6) | |
H6 | 0.9623 | −0.1903 | 0.7418 | 0.035* | |
C7 | 0.92282 (16) | 0.0221 (3) | 0.73140 (10) | 0.0261 (6) | |
H7 | 0.9186 | 0.0429 | 0.7680 | 0.031* | |
C8 | 0.90270 (13) | 0.1329 (3) | 0.69407 (9) | 0.0171 (5) | |
C9 | 0.87267 (13) | 0.2809 (3) | 0.70961 (9) | 0.0163 (5) | |
C10 | 0.85475 (15) | 0.3109 (3) | 0.76247 (10) | 0.0234 (6) | |
H10 | 0.8625 | 0.2351 | 0.7885 | 0.028* | |
C11 | 0.82627 (16) | 0.4481 (3) | 0.77695 (10) | 0.0274 (6) | |
H11 | 0.8144 | 0.4656 | 0.8128 | 0.033* | |
C12 | 0.81468 (16) | 0.5607 (3) | 0.74001 (10) | 0.0272 (6) | |
H12 | 0.7955 | 0.6555 | 0.7503 | 0.033* | |
C13 | 0.83150 (14) | 0.5335 (3) | 0.68758 (10) | 0.0218 (5) | |
H13 | 0.8236 | 0.6103 | 0.6619 | 0.026* | |
C14 | 0.85986 (13) | 0.3944 (3) | 0.67232 (9) | 0.0149 (5) | |
C15 | 0.81596 (13) | 0.4414 (2) | 0.57728 (9) | 0.0139 (5) | |
C16 | 0.73893 (13) | 0.4104 (3) | 0.57548 (9) | 0.0155 (5) | |
H16 | 0.7181 | 0.3371 | 0.5981 | 0.019* | |
C17 | 0.69262 (13) | 0.4903 (3) | 0.53939 (9) | 0.0153 (5) | |
C18 | 0.72257 (14) | 0.5961 (3) | 0.50532 (9) | 0.0171 (5) | |
H18 | 0.6899 | 0.6465 | 0.4802 | 0.021* | |
C19 | 0.80014 (14) | 0.6276 (3) | 0.50815 (9) | 0.0164 (5) | |
H19 | 0.8210 | 0.7007 | 0.4855 | 0.020* | |
C20 | 0.84714 (13) | 0.5506 (3) | 0.54469 (9) | 0.0150 (5) | |
C21 | 0.92914 (13) | 0.5620 (2) | 0.55759 (9) | 0.0144 (5) | |
C22 | 0.98559 (13) | 0.6525 (3) | 0.53700 (9) | 0.0170 (5) | |
H22 | 0.9732 | 0.7227 | 0.5097 | 0.020* | |
C23 | 1.06016 (14) | 0.6384 (3) | 0.55690 (10) | 0.0201 (5) | |
H23 | 1.0994 | 0.6990 | 0.5432 | 0.024* | |
C24 | 1.07723 (13) | 0.5356 (3) | 0.59686 (10) | 0.0187 (5) | |
C25 | 1.02210 (13) | 0.4439 (3) | 0.61843 (9) | 0.0168 (5) | |
H25 | 1.0348 | 0.3738 | 0.6457 | 0.020* | |
C26 | 0.94788 (13) | 0.4597 (2) | 0.59830 (9) | 0.0144 (5) | |
Br3 | 0.11825 (2) | 0.06102 (3) | 0.58188 (2) | 0.02152 (6) | |
Br4 | 0.72200 (2) | −0.00951 (3) | 0.61494 (2) | 0.02122 (6) | |
O2 | 0.44110 (9) | 0.33247 (19) | 0.57462 (6) | 0.0209 (4) | |
C27 | 0.42160 (12) | 0.1372 (2) | 0.63726 (9) | 0.0126 (4) | |
C28 | 0.42082 (12) | 0.3019 (3) | 0.61883 (9) | 0.0141 (5) | |
C29 | 0.38932 (13) | 0.4159 (3) | 0.65432 (9) | 0.0155 (5) | |
C30 | 0.37581 (14) | 0.5601 (3) | 0.63376 (10) | 0.0212 (5) | |
H30 | 0.3881 | 0.5825 | 0.5983 | 0.025* | |
C31 | 0.34463 (15) | 0.6697 (3) | 0.66509 (11) | 0.0257 (6) | |
H31 | 0.3355 | 0.7674 | 0.6513 | 0.031* | |
C32 | 0.32685 (15) | 0.6360 (3) | 0.71668 (11) | 0.0265 (6) | |
H32 | 0.3054 | 0.7111 | 0.7382 | 0.032* | |
C33 | 0.34006 (15) | 0.4940 (3) | 0.73721 (10) | 0.0229 (5) | |
H33 | 0.3269 | 0.4728 | 0.7725 | 0.028* | |
C34 | 0.37253 (13) | 0.3811 (3) | 0.70678 (9) | 0.0166 (5) | |
C35 | 0.39221 (13) | 0.2317 (3) | 0.72944 (9) | 0.0151 (5) | |
C36 | 0.38903 (15) | 0.2040 (3) | 0.78410 (10) | 0.0231 (6) | |
H36 | 0.3728 | 0.2818 | 0.8068 | 0.028* | |
C37 | 0.40892 (15) | 0.0663 (3) | 0.80551 (10) | 0.0251 (6) | |
H37 | 0.4060 | 0.0497 | 0.8425 | 0.030* | |
C38 | 0.43320 (14) | −0.0476 (3) | 0.77287 (10) | 0.0218 (5) | |
H38 | 0.4465 | −0.1427 | 0.7874 | 0.026* | |
C39 | 0.43804 (13) | −0.0223 (3) | 0.71900 (9) | 0.0174 (5) | |
H39 | 0.4554 | −0.1003 | 0.6968 | 0.021* | |
C40 | 0.41770 (13) | 0.1161 (3) | 0.69691 (9) | 0.0138 (5) | |
C41 | 0.35281 (13) | 0.0666 (2) | 0.60646 (9) | 0.0137 (5) | |
C42 | 0.27603 (13) | 0.0989 (3) | 0.61086 (9) | 0.0151 (5) | |
H42 | 0.2590 | 0.1693 | 0.6361 | 0.018* | |
C43 | 0.22452 (13) | 0.0234 (3) | 0.57650 (9) | 0.0165 (5) | |
C44 | 0.24804 (14) | −0.0779 (3) | 0.53878 (9) | 0.0202 (5) | |
H44 | 0.2115 | −0.1262 | 0.5158 | 0.024* | |
C45 | 0.32557 (14) | −0.1082 (3) | 0.53493 (10) | 0.0207 (5) | |
H45 | 0.3425 | −0.1773 | 0.5093 | 0.025* | |
C46 | 0.37807 (14) | −0.0363 (3) | 0.56894 (9) | 0.0160 (5) | |
C47 | 0.46145 (13) | −0.0465 (3) | 0.57357 (9) | 0.0162 (5) | |
C48 | 0.51275 (14) | −0.1339 (3) | 0.54643 (10) | 0.0219 (5) | |
H48 | 0.4950 | −0.2014 | 0.5196 | 0.026* | |
C49 | 0.59027 (14) | −0.1209 (3) | 0.55918 (10) | 0.0212 (5) | |
H49 | 0.6262 | −0.1797 | 0.5411 | 0.025* | |
C50 | 0.61495 (13) | −0.0219 (3) | 0.59844 (10) | 0.0171 (5) | |
C51 | 0.56498 (13) | 0.0679 (3) | 0.62596 (9) | 0.0155 (5) | |
H51 | 0.5831 | 0.1360 | 0.6525 | 0.019* | |
C52 | 0.48773 (13) | 0.0537 (2) | 0.61306 (9) | 0.0142 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01159 (11) | 0.02131 (12) | 0.01997 (12) | 0.00043 (9) | −0.00161 (9) | −0.00174 (9) |
Br2 | 0.01206 (12) | 0.04248 (16) | 0.02601 (14) | −0.00319 (11) | −0.00067 (10) | −0.01276 (12) |
O1 | 0.0257 (9) | 0.0190 (8) | 0.0141 (8) | 0.0006 (7) | −0.0001 (7) | −0.0026 (7) |
C1 | 0.0126 (11) | 0.0148 (11) | 0.0129 (11) | −0.0016 (9) | 0.0004 (9) | 0.0004 (9) |
C2 | 0.0081 (11) | 0.0158 (11) | 0.0182 (12) | −0.0033 (9) | 0.0005 (9) | −0.0005 (9) |
C3 | 0.0085 (11) | 0.0165 (11) | 0.0166 (11) | −0.0018 (9) | −0.0001 (9) | 0.0005 (9) |
C4 | 0.0154 (12) | 0.0177 (12) | 0.0200 (12) | 0.0006 (10) | −0.0003 (10) | −0.0024 (10) |
C5 | 0.0239 (14) | 0.0147 (12) | 0.0331 (15) | 0.0052 (10) | 0.0000 (11) | 0.0007 (10) |
C6 | 0.0375 (16) | 0.0235 (14) | 0.0249 (14) | 0.0085 (12) | −0.0043 (12) | 0.0075 (11) |
C7 | 0.0339 (15) | 0.0270 (14) | 0.0175 (13) | 0.0041 (12) | 0.0013 (11) | 0.0026 (11) |
C8 | 0.0133 (12) | 0.0197 (12) | 0.0181 (12) | −0.0008 (9) | 0.0000 (9) | 0.0014 (10) |
C9 | 0.0120 (11) | 0.0218 (12) | 0.0152 (12) | 0.0000 (9) | 0.0008 (9) | −0.0002 (9) |
C10 | 0.0242 (14) | 0.0306 (14) | 0.0155 (12) | 0.0035 (11) | 0.0032 (10) | 0.0002 (10) |
C11 | 0.0281 (15) | 0.0379 (16) | 0.0167 (12) | 0.0029 (12) | 0.0073 (11) | −0.0056 (11) |
C12 | 0.0296 (15) | 0.0265 (14) | 0.0256 (14) | 0.0069 (12) | 0.0035 (11) | −0.0092 (11) |
C13 | 0.0217 (13) | 0.0218 (13) | 0.0219 (13) | 0.0038 (10) | 0.0016 (10) | −0.0016 (10) |
C14 | 0.0106 (11) | 0.0198 (12) | 0.0143 (11) | −0.0008 (9) | 0.0000 (9) | −0.0029 (9) |
C15 | 0.0146 (11) | 0.0134 (11) | 0.0135 (11) | 0.0019 (9) | 0.0001 (9) | −0.0009 (9) |
C16 | 0.0159 (12) | 0.0155 (11) | 0.0151 (11) | −0.0007 (9) | 0.0017 (9) | 0.0011 (9) |
C17 | 0.0092 (11) | 0.0186 (12) | 0.0180 (12) | 0.0010 (9) | −0.0001 (9) | −0.0025 (9) |
C18 | 0.0171 (12) | 0.0199 (12) | 0.0144 (11) | 0.0045 (10) | 0.0000 (9) | 0.0000 (9) |
C19 | 0.0205 (12) | 0.0151 (12) | 0.0137 (11) | 0.0008 (9) | 0.0034 (10) | 0.0034 (9) |
C20 | 0.0151 (12) | 0.0149 (11) | 0.0153 (11) | 0.0005 (9) | 0.0044 (9) | −0.0030 (9) |
C21 | 0.0147 (11) | 0.0145 (11) | 0.0142 (11) | −0.0008 (9) | 0.0026 (9) | −0.0033 (9) |
C22 | 0.0193 (12) | 0.0147 (11) | 0.0174 (12) | −0.0017 (10) | 0.0051 (10) | −0.0026 (9) |
C23 | 0.0176 (12) | 0.0197 (12) | 0.0235 (13) | −0.0062 (10) | 0.0082 (10) | −0.0079 (10) |
C24 | 0.0112 (11) | 0.0242 (13) | 0.0207 (12) | −0.0016 (10) | 0.0007 (9) | −0.0119 (10) |
C25 | 0.0143 (12) | 0.0202 (12) | 0.0159 (11) | 0.0007 (10) | 0.0004 (9) | −0.0055 (9) |
C26 | 0.0135 (11) | 0.0157 (11) | 0.0142 (11) | 0.0001 (9) | 0.0039 (9) | −0.0061 (9) |
Br3 | 0.01114 (12) | 0.02792 (13) | 0.02541 (13) | −0.00354 (10) | −0.00065 (9) | 0.00470 (10) |
Br4 | 0.01141 (12) | 0.02510 (13) | 0.02731 (13) | 0.00130 (9) | 0.00279 (9) | 0.00374 (10) |
O2 | 0.0185 (9) | 0.0245 (9) | 0.0200 (9) | −0.0008 (7) | 0.0050 (7) | 0.0069 (7) |
C27 | 0.0087 (11) | 0.0165 (11) | 0.0126 (11) | −0.0010 (9) | 0.0007 (9) | −0.0004 (9) |
C28 | 0.0076 (11) | 0.0178 (11) | 0.0167 (12) | −0.0022 (9) | −0.0035 (9) | 0.0023 (9) |
C29 | 0.0099 (11) | 0.0152 (11) | 0.0210 (12) | −0.0023 (9) | −0.0034 (9) | 0.0000 (9) |
C30 | 0.0157 (12) | 0.0189 (12) | 0.0283 (14) | −0.0050 (10) | −0.0058 (10) | 0.0048 (10) |
C31 | 0.0228 (14) | 0.0139 (12) | 0.0398 (16) | −0.0013 (10) | −0.0087 (12) | −0.0017 (11) |
C32 | 0.0240 (14) | 0.0193 (13) | 0.0356 (16) | 0.0040 (11) | −0.0061 (12) | −0.0113 (11) |
C33 | 0.0224 (13) | 0.0241 (13) | 0.0221 (13) | −0.0011 (11) | −0.0022 (10) | −0.0058 (10) |
C34 | 0.0112 (11) | 0.0187 (12) | 0.0194 (12) | −0.0040 (9) | −0.0040 (9) | −0.0034 (10) |
C35 | 0.0122 (11) | 0.0194 (12) | 0.0137 (11) | −0.0030 (9) | −0.0007 (9) | −0.0014 (9) |
C36 | 0.0249 (14) | 0.0274 (14) | 0.0172 (12) | 0.0001 (11) | 0.0021 (10) | −0.0026 (10) |
C37 | 0.0251 (14) | 0.0362 (15) | 0.0141 (12) | −0.0023 (12) | 0.0006 (10) | 0.0049 (11) |
C38 | 0.0190 (13) | 0.0239 (13) | 0.0222 (13) | −0.0020 (10) | −0.0021 (10) | 0.0095 (10) |
C39 | 0.0152 (12) | 0.0182 (12) | 0.0186 (12) | −0.0009 (9) | −0.0006 (9) | 0.0000 (9) |
C40 | 0.0099 (11) | 0.0185 (11) | 0.0128 (11) | −0.0046 (9) | −0.0017 (9) | 0.0005 (9) |
C41 | 0.0143 (11) | 0.0149 (11) | 0.0116 (11) | −0.0027 (9) | −0.0013 (9) | 0.0026 (9) |
C42 | 0.0140 (11) | 0.0173 (11) | 0.0141 (11) | −0.0020 (9) | 0.0024 (9) | 0.0028 (9) |
C43 | 0.0104 (11) | 0.0230 (12) | 0.0160 (11) | −0.0021 (9) | −0.0004 (9) | 0.0062 (9) |
C44 | 0.0181 (13) | 0.0255 (13) | 0.0169 (12) | −0.0078 (10) | −0.0015 (10) | −0.0001 (10) |
C45 | 0.0197 (13) | 0.0251 (13) | 0.0175 (12) | −0.0044 (11) | 0.0015 (10) | −0.0048 (10) |
C46 | 0.0169 (12) | 0.0173 (12) | 0.0139 (11) | −0.0024 (10) | 0.0014 (9) | 0.0002 (9) |
C47 | 0.0161 (12) | 0.0167 (11) | 0.0158 (11) | −0.0017 (9) | 0.0010 (9) | 0.0006 (9) |
C48 | 0.0214 (13) | 0.0212 (13) | 0.0232 (13) | −0.0004 (10) | 0.0029 (10) | −0.0070 (10) |
C49 | 0.0175 (13) | 0.0205 (13) | 0.0262 (13) | 0.0019 (10) | 0.0067 (10) | −0.0026 (10) |
C50 | 0.0108 (11) | 0.0186 (12) | 0.0219 (12) | 0.0003 (9) | 0.0018 (9) | 0.0044 (10) |
C51 | 0.0139 (11) | 0.0172 (11) | 0.0154 (11) | −0.0013 (9) | 0.0003 (9) | 0.0004 (9) |
C52 | 0.0146 (11) | 0.0135 (11) | 0.0147 (11) | 0.0013 (9) | 0.0025 (9) | 0.0026 (9) |
Br1—C17 | 1.890 (2) | Br3—C43 | 1.901 (2) |
Br2—C24 | 1.896 (2) | Br4—C50 | 1.908 (2) |
O1—C2 | 1.219 (3) | O2—C28 | 1.216 (3) |
C1—C15 | 1.520 (3) | C27—C40 | 1.523 (3) |
C1—C14 | 1.529 (3) | C27—C52 | 1.524 (3) |
C1—C26 | 1.536 (3) | C27—C28 | 1.541 (3) |
C1—C2 | 1.541 (3) | C27—C41 | 1.544 (3) |
C2—C3 | 1.475 (3) | C28—C29 | 1.476 (3) |
C3—C4 | 1.407 (3) | C29—C34 | 1.404 (3) |
C3—C8 | 1.407 (3) | C29—C30 | 1.405 (3) |
C4—C5 | 1.381 (3) | C30—C31 | 1.383 (4) |
C4—H4 | 0.9500 | C30—H30 | 0.9500 |
C5—C6 | 1.384 (4) | C31—C32 | 1.385 (4) |
C5—H5 | 0.9500 | C31—H31 | 0.9500 |
C6—C7 | 1.387 (4) | C32—C33 | 1.385 (4) |
C6—H6 | 0.9500 | C32—H32 | 0.9500 |
C7—C8 | 1.402 (3) | C33—C34 | 1.401 (3) |
C7—H7 | 0.9500 | C33—H33 | 0.9500 |
C8—C9 | 1.480 (3) | C34—C35 | 1.485 (3) |
C9—C14 | 1.395 (3) | C35—C40 | 1.403 (3) |
C9—C10 | 1.409 (3) | C35—C36 | 1.407 (3) |
C10—C11 | 1.377 (4) | C36—C37 | 1.382 (4) |
C10—H10 | 0.9500 | C36—H36 | 0.9500 |
C11—C12 | 1.381 (4) | C37—C38 | 1.385 (4) |
C11—H11 | 0.9500 | C37—H37 | 0.9500 |
C12—C13 | 1.390 (4) | C38—C39 | 1.386 (3) |
C12—H12 | 0.9500 | C38—H38 | 0.9500 |
C13—C14 | 1.396 (3) | C39—C40 | 1.396 (3) |
C13—H13 | 0.9500 | C39—H39 | 0.9500 |
C15—C16 | 1.376 (3) | C41—C42 | 1.384 (3) |
C15—C20 | 1.400 (3) | C41—C46 | 1.403 (3) |
C16—C17 | 1.394 (3) | C42—C43 | 1.401 (3) |
C16—H16 | 0.9500 | C42—H42 | 0.9500 |
C17—C18 | 1.393 (3) | C43—C44 | 1.388 (3) |
C18—C19 | 1.386 (3) | C44—C45 | 1.391 (3) |
C18—H18 | 0.9500 | C44—H44 | 0.9500 |
C19—C20 | 1.395 (3) | C45—C46 | 1.391 (3) |
C19—H19 | 0.9500 | C45—H45 | 0.9500 |
C20—C21 | 1.464 (3) | C46—C47 | 1.463 (3) |
C21—C22 | 1.392 (3) | C47—C48 | 1.390 (3) |
C21—C26 | 1.405 (3) | C47—C52 | 1.404 (3) |
C22—C23 | 1.387 (3) | C48—C49 | 1.388 (3) |
C22—H22 | 0.9500 | C48—H48 | 0.9500 |
C23—C24 | 1.389 (4) | C49—C50 | 1.386 (3) |
C23—H23 | 0.9500 | C49—H49 | 0.9500 |
C24—C25 | 1.392 (3) | C50—C51 | 1.392 (3) |
C25—C26 | 1.385 (3) | C51—C52 | 1.385 (3) |
C25—H25 | 0.9500 | C51—H51 | 0.9500 |
C15—C1—C14 | 112.13 (18) | C40—C27—C52 | 113.59 (18) |
C15—C1—C26 | 100.90 (18) | C40—C27—C28 | 114.62 (19) |
C14—C1—C26 | 111.76 (18) | C52—C27—C28 | 110.03 (18) |
C15—C1—C2 | 110.29 (18) | C40—C27—C41 | 112.67 (18) |
C14—C1—C2 | 114.57 (19) | C52—C27—C41 | 100.86 (18) |
C26—C1—C2 | 106.20 (18) | C28—C27—C41 | 103.81 (17) |
O1—C2—C3 | 121.9 (2) | O2—C28—C29 | 122.2 (2) |
O1—C2—C1 | 119.5 (2) | O2—C28—C27 | 119.5 (2) |
C3—C2—C1 | 118.55 (19) | C29—C28—C27 | 118.16 (19) |
C4—C3—C8 | 120.6 (2) | C34—C29—C30 | 120.9 (2) |
C4—C3—C2 | 117.9 (2) | C34—C29—C28 | 121.2 (2) |
C8—C3—C2 | 121.5 (2) | C30—C29—C28 | 117.9 (2) |
C5—C4—C3 | 120.4 (2) | C31—C30—C29 | 120.0 (2) |
C5—C4—H4 | 119.8 | C31—C30—H30 | 120.0 |
C3—C4—H4 | 119.8 | C29—C30—H30 | 120.0 |
C4—C5—C6 | 119.2 (2) | C30—C31—C32 | 119.6 (2) |
C4—C5—H5 | 120.4 | C30—C31—H31 | 120.2 |
C6—C5—H5 | 120.4 | C32—C31—H31 | 120.2 |
C5—C6—C7 | 121.1 (2) | C33—C32—C31 | 120.7 (2) |
C5—C6—H6 | 119.5 | C33—C32—H32 | 119.6 |
C7—C6—H6 | 119.5 | C31—C32—H32 | 119.6 |
C6—C7—C8 | 121.1 (2) | C32—C33—C34 | 121.1 (2) |
C6—C7—H7 | 119.5 | C32—C33—H33 | 119.4 |
C8—C7—H7 | 119.5 | C34—C33—H33 | 119.4 |
C7—C8—C3 | 117.6 (2) | C33—C34—C29 | 117.6 (2) |
C7—C8—C9 | 122.2 (2) | C33—C34—C35 | 121.7 (2) |
C3—C8—C9 | 120.2 (2) | C29—C34—C35 | 120.6 (2) |
C14—C9—C10 | 117.8 (2) | C40—C35—C36 | 118.2 (2) |
C14—C9—C8 | 121.2 (2) | C40—C35—C34 | 120.5 (2) |
C10—C9—C8 | 121.0 (2) | C36—C35—C34 | 121.3 (2) |
C11—C10—C9 | 121.1 (2) | C37—C36—C35 | 121.4 (2) |
C11—C10—H10 | 119.4 | C37—C36—H36 | 119.3 |
C9—C10—H10 | 119.4 | C35—C36—H36 | 119.3 |
C10—C11—C12 | 120.8 (2) | C36—C37—C38 | 119.8 (2) |
C10—C11—H11 | 119.6 | C36—C37—H37 | 120.1 |
C12—C11—H11 | 119.6 | C38—C37—H37 | 120.1 |
C11—C12—C13 | 119.1 (2) | C37—C38—C39 | 119.9 (2) |
C11—C12—H12 | 120.4 | C37—C38—H38 | 120.1 |
C13—C12—H12 | 120.4 | C39—C38—H38 | 120.1 |
C12—C13—C14 | 120.6 (2) | C38—C39—C40 | 120.8 (2) |
C12—C13—H13 | 119.7 | C38—C39—H39 | 119.6 |
C14—C13—H13 | 119.7 | C40—C39—H39 | 119.6 |
C9—C14—C13 | 120.5 (2) | C39—C40—C35 | 119.9 (2) |
C9—C14—C1 | 121.5 (2) | C39—C40—C27 | 119.0 (2) |
C13—C14—C1 | 117.9 (2) | C35—C40—C27 | 121.1 (2) |
C16—C15—C20 | 121.6 (2) | C42—C41—C46 | 121.5 (2) |
C16—C15—C1 | 127.0 (2) | C42—C41—C27 | 128.0 (2) |
C20—C15—C1 | 111.3 (2) | C46—C41—C27 | 110.35 (19) |
C15—C16—C17 | 117.7 (2) | C41—C42—C43 | 117.0 (2) |
C15—C16—H16 | 121.2 | C41—C42—H42 | 121.5 |
C17—C16—H16 | 121.2 | C43—C42—H42 | 121.5 |
C18—C17—C16 | 121.9 (2) | C44—C43—C42 | 122.6 (2) |
C18—C17—Br1 | 120.57 (17) | C44—C43—Br3 | 118.75 (18) |
C16—C17—Br1 | 117.56 (17) | C42—C43—Br3 | 118.68 (18) |
C19—C18—C17 | 119.8 (2) | C43—C44—C45 | 119.4 (2) |
C19—C18—H18 | 120.1 | C43—C44—H44 | 120.3 |
C17—C18—H18 | 120.1 | C45—C44—H44 | 120.3 |
C18—C19—C20 | 119.1 (2) | C46—C45—C44 | 119.4 (2) |
C18—C19—H19 | 120.4 | C46—C45—H45 | 120.3 |
C20—C19—H19 | 120.4 | C44—C45—H45 | 120.3 |
C19—C20—C15 | 119.9 (2) | C45—C46—C41 | 120.1 (2) |
C19—C20—C21 | 131.5 (2) | C45—C46—C47 | 130.9 (2) |
C15—C20—C21 | 108.6 (2) | C41—C46—C47 | 109.0 (2) |
C22—C21—C26 | 120.1 (2) | C48—C47—C52 | 120.5 (2) |
C22—C21—C20 | 131.4 (2) | C48—C47—C46 | 131.1 (2) |
C26—C21—C20 | 108.5 (2) | C52—C47—C46 | 108.5 (2) |
C23—C22—C21 | 119.0 (2) | C49—C48—C47 | 118.9 (2) |
C23—C22—H22 | 120.5 | C49—C48—H48 | 120.5 |
C21—C22—H22 | 120.5 | C47—C48—H48 | 120.5 |
C22—C23—C24 | 119.8 (2) | C50—C49—C48 | 119.7 (2) |
C22—C23—H23 | 120.1 | C50—C49—H49 | 120.2 |
C24—C23—H23 | 120.1 | C48—C49—H49 | 120.2 |
C23—C24—C25 | 122.7 (2) | C49—C50—C51 | 122.7 (2) |
C23—C24—Br2 | 118.51 (18) | C49—C50—Br4 | 118.06 (18) |
C25—C24—Br2 | 118.82 (19) | C51—C50—Br4 | 119.25 (18) |
C26—C25—C24 | 116.8 (2) | C52—C51—C50 | 117.2 (2) |
C26—C25—H25 | 121.6 | C52—C51—H51 | 121.4 |
C24—C25—H25 | 121.6 | C50—C51—H51 | 121.4 |
C25—C26—C21 | 121.7 (2) | C51—C52—C47 | 121.1 (2) |
C25—C26—C1 | 127.6 (2) | C51—C52—C27 | 127.6 (2) |
C21—C26—C1 | 110.6 (2) | C47—C52—C27 | 111.3 (2) |
Cg2, Cg3, Cg6, Cg15 and Cg17 are the centroids of the C1–C3/C8/C9/C14, C3–C8, C21–C26, C29–C24 and C41–C46 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C44—H44···O1i | 0.95 | 2.44 | 3.364 (3) | 163 |
C5—H5···Cg6ii | 0.95 | 2.69 | 3.554 (3) | 151 |
C31—H31···Cg17iii | 0.95 | 2.88 | 3.780 (3) | 158 |
C24—Br2···Cg15iv | 1.90 (1) | 3.44 (1) | 5.330 (3) | 173 (1) |
C50—Br4···Cg2 | 1.91 (1) | 3.78 (1) | 5.454 (3) | 145 (1) |
C50—Br4···Cg3 | 1.91 (1) | 3.91 (1) | 5.790 (3) | 168 (1) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y−1, z; (iii) x, y+1, z; (iv) x+1, y, z. |
Funding information
Funding for this research was provided by: Ministry of Science and Technology, Taiwanhttps://doi.org/10.13039/501100004663 (award No. MOST 103–2113-M-029–007-MY2); Ministry of Education, Culture, Sports, Science and Technology (MEXT), World Premier International Research Centre Initiative (WPI)
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