

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808033369/at2650sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808033369/at2650Isup2.hkl |
CCDC reference: 709375
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.011 Å
- R factor = 0.036
- wR factor = 0.103
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10 Absorption corrections should be applied. Tmin and Tmax expected: 0.503 0.588 RT(exp) = 1.171 Value of measurement temperature given = 293.000 Value of melting point given = 0.000 STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.490 From the CIF: _refine_ls_abs_structure_Flack_su 0.020 PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.18 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.45 Ratio PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 11
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 6024 Count of symmetry unique reflns 3258 Completeness (_total/calc) 184.90% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2766 Fraction of Friedel pairs measured 0.849 Are heavy atom types Z>Si present yes PLAT033_ALERT_4_G Flack Parameter Value Deviates from Zero ....... 0.49 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of the 6-bromo-1-(2-bromo-6-hydroxynaphthalen-5-yl) naphthalen-2-ol (0.1 mol), and 1-iodohexane (0.22 mol) was stirred in refluxing acetone/K2CO3 mixture (20 mL) for 4 h to afford the title compound (0.086 mol, yield 86%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.
H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93 - 0.97 Å, and with Uiso=1.2–1.5Ueq(C,N).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
C32H36Br2O2 | F(000) = 1256 |
Mr = 612.43 | Dx = 1.465 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 1536 reflections |
a = 12.401 (3) Å | θ = 2.5–23.6° |
b = 8.1742 (16) Å | µ = 2.95 mm−1 |
c = 27.396 (6) Å | T = 293 K |
V = 2777.1 (10) Å3 | Block, yellow |
Z = 4 | 0.25 × 0.20 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 3581 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 27.5°, θmin = 1.5° |
ϕ and ω scans | h = −16→16 |
26425 measured reflections | k = −10→10 |
3647 independent reflections | l = −35→35 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.031P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max = 0.002 |
3647 reflections | Δρmax = 0.53 e Å−3 |
325 parameters | Δρmin = −0.38 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2766 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.49 (2) |
C32H36Br2O2 | V = 2777.1 (10) Å3 |
Mr = 612.43 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 12.401 (3) Å | µ = 2.95 mm−1 |
b = 8.1742 (16) Å | T = 293 K |
c = 27.396 (6) Å | 0.25 × 0.20 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 3581 reflections with I > 2σ(I) |
26425 measured reflections | Rint = 0.062 |
3647 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.103 | Δρmax = 0.53 e Å−3 |
S = 0.91 | Δρmin = −0.38 e Å−3 |
3647 reflections | Absolute structure: Flack (1983), 2766 Freidel pairs |
325 parameters | Absolute structure parameter: 0.49 (2) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.72348 (8) | 0.71557 (12) | 0.21977 (2) | 0.0350 (2) | |
Br2 | 0.02939 (8) | 0.71401 (13) | 0.52428 (2) | 0.0354 (2) | |
C25 | 0.2283 (6) | 0.7910 (11) | 0.4792 (4) | 0.0289 (19) | |
H25A | 0.2582 | 0.7353 | 0.5055 | 0.035* | |
O1 | 0.4163 (4) | 1.1960 (8) | 0.4440 (2) | 0.0311 (12) | |
O2 | 0.3351 (4) | 1.1966 (8) | 0.2989 (2) | 0.0314 (12) | |
C30 | 0.5435 (7) | 1.2962 (13) | 0.1715 (4) | 0.0310 (19) | |
H30A | 0.5845 | 1.3763 | 0.1899 | 0.037* | |
H30B | 0.5045 | 1.3541 | 0.1461 | 0.037* | |
C14 | 0.5233 (6) | 0.7941 (12) | 0.2653 (4) | 0.0297 (19) | |
H14A | 0.4927 | 0.7390 | 0.2390 | 0.036* | |
C3 | 0.2086 (7) | 1.2922 (12) | 0.5727 (4) | 0.031 (2) | |
H3A | 0.2469 | 1.3490 | 0.5986 | 0.037* | |
H3B | 0.1663 | 1.3727 | 0.5552 | 0.037* | |
C6 | 0.4604 (9) | 1.2618 (8) | 0.4870 (4) | 0.019 (2) | |
H6A | 0.5139 | 1.3441 | 0.4789 | 0.022* | |
H6B | 0.4956 | 1.1761 | 0.5056 | 0.022* | |
C24 | 0.1149 (5) | 0.8051 (10) | 0.4732 (3) | 0.0267 (16) | |
C27 | 0.2915 (10) | 1.2656 (11) | 0.2526 (5) | 0.040 (3) | |
H27A | 0.2371 | 1.3475 | 0.2595 | 0.048* | |
H27B | 0.2591 | 1.1798 | 0.2330 | 0.048* | |
C8 | 0.5971 (6) | 1.1092 (9) | 0.4195 (3) | 0.0295 (17) | |
H8A | 0.6277 | 1.1601 | 0.4465 | 0.035* | |
C16 | 0.6830 (5) | 0.8758 (9) | 0.3093 (3) | 0.0272 (16) | |
H16A | 0.7577 | 0.8774 | 0.3124 | 0.033* | |
C10 | 0.6174 (5) | 0.9496 (9) | 0.3456 (3) | 0.0223 (16) | |
C15 | 0.6363 (5) | 0.8027 (11) | 0.2699 (3) | 0.0253 (15) | |
C11 | 0.5035 (5) | 0.9499 (8) | 0.3400 (3) | 0.0226 (15) | |
C29 | 0.4653 (8) | 1.2176 (11) | 0.2043 (4) | 0.038 (2) | |
H29A | 0.5039 | 1.1641 | 0.2306 | 0.046* | |
H29B | 0.4262 | 1.1342 | 0.1864 | 0.046* | |
C4 | 0.2923 (7) | 1.2171 (10) | 0.5372 (3) | 0.0260 (19) | |
H4A | 0.3319 | 1.1320 | 0.5542 | 0.031* | |
H4B | 0.2543 | 1.1662 | 0.5102 | 0.031* | |
C19 | 0.1345 (6) | 0.9496 (9) | 0.3975 (3) | 0.0257 (17) | |
C22 | 0.2678 (6) | 1.1123 (8) | 0.3292 (2) | 0.0258 (16) | |
C17 | 0.3157 (5) | 1.0338 (9) | 0.3686 (3) | 0.0260 (17) | |
C23 | 0.0695 (5) | 0.8747 (9) | 0.4339 (3) | 0.0275 (16) | |
H23A | −0.0051 | 0.8739 | 0.4305 | 0.033* | |
C32 | 0.7062 (12) | 1.2663 (12) | 0.1191 (6) | 0.051 (4) | |
H32A | 0.7554 | 1.1890 | 0.1050 | 0.076* | |
H32B | 0.7450 | 1.3386 | 0.1405 | 0.076* | |
H32C | 0.6725 | 1.3288 | 0.0937 | 0.076* | |
C12 | 0.4362 (5) | 1.0324 (9) | 0.3741 (2) | 0.0236 (17) | |
C28 | 0.3838 (5) | 1.3404 (8) | 0.2262 (3) | 0.0317 (17) | |
H28A | 0.4220 | 1.4119 | 0.2485 | 0.038* | |
H28B | 0.3556 | 1.4078 | 0.2000 | 0.038* | |
C9 | 0.6621 (6) | 1.0310 (10) | 0.3865 (3) | 0.0292 (18) | |
H9A | 0.7364 | 1.0314 | 0.3911 | 0.035* | |
C18 | 0.2499 (5) | 0.9489 (9) | 0.4030 (3) | 0.0228 (15) | |
C20 | 0.0909 (6) | 1.0301 (9) | 0.3560 (3) | 0.0270 (18) | |
H20A | 0.0166 | 1.0290 | 0.3513 | 0.032* | |
C7 | 0.4848 (6) | 1.1134 (8) | 0.4131 (2) | 0.0248 (16) | |
C21 | 0.1543 (6) | 1.1093 (9) | 0.3226 (3) | 0.0295 (17) | |
H21A | 0.1232 | 1.1607 | 0.2958 | 0.035* | |
C5 | 0.3706 (5) | 1.3383 (8) | 0.5173 (3) | 0.0321 (17) | |
H5A | 0.4026 | 1.3981 | 0.5442 | 0.038* | |
H5B | 0.3319 | 1.4163 | 0.4972 | 0.038* | |
C13 | 0.4596 (6) | 0.8659 (8) | 0.2989 (2) | 0.0284 (16) | |
H13A | 0.3851 | 0.8605 | 0.2952 | 0.034* | |
C26 | 0.2926 (6) | 0.8645 (8) | 0.4437 (2) | 0.0273 (16) | |
H26A | 0.3671 | 0.8578 | 0.4470 | 0.033* | |
C31 | 0.6215 (6) | 1.1766 (9) | 0.1477 (3) | 0.0332 (18) | |
H31A | 0.6557 | 1.1106 | 0.1727 | 0.040* | |
H31B | 0.5821 | 1.1040 | 0.1261 | 0.040* | |
C2 | 0.1328 (6) | 1.1696 (10) | 0.5956 (3) | 0.0362 (19) | |
H2A | 0.1740 | 1.0951 | 0.6159 | 0.043* | |
H2B | 0.0988 | 1.1059 | 0.5701 | 0.043* | |
C1 | 0.0439 (10) | 1.2518 (8) | 0.6272 (6) | 0.033 (3) | |
H1A | −0.0008 | 1.1690 | 0.6417 | 0.049* | |
H1B | 0.0005 | 1.3216 | 0.6070 | 0.049* | |
H1C | 0.0770 | 1.3157 | 0.6525 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0306 (5) | 0.0454 (4) | 0.0291 (5) | 0.0060 (5) | 0.0042 (4) | 0.0017 (9) |
Br2 | 0.0305 (5) | 0.0448 (4) | 0.0308 (5) | −0.0055 (5) | 0.0024 (4) | 0.0072 (9) |
C25 | 0.027 (4) | 0.029 (4) | 0.031 (5) | 0.000 (4) | −0.004 (3) | −0.006 (5) |
O1 | 0.026 (3) | 0.046 (3) | 0.022 (3) | 0.003 (3) | −0.003 (2) | −0.007 (3) |
O2 | 0.027 (3) | 0.041 (3) | 0.026 (3) | −0.002 (3) | −0.004 (2) | 0.010 (3) |
C30 | 0.033 (5) | 0.034 (4) | 0.026 (5) | 0.000 (5) | −0.005 (3) | −0.005 (5) |
C14 | 0.033 (5) | 0.034 (4) | 0.022 (5) | 0.000 (4) | −0.003 (3) | −0.007 (5) |
C3 | 0.031 (5) | 0.032 (4) | 0.030 (5) | 0.006 (4) | 0.001 (3) | −0.010 (5) |
C6 | 0.024 (5) | 0.024 (5) | 0.008 (4) | −0.003 (3) | 0.002 (3) | 0.000 (3) |
C24 | 0.028 (4) | 0.023 (4) | 0.029 (4) | −0.004 (4) | 0.004 (3) | −0.006 (4) |
C27 | 0.041 (7) | 0.042 (6) | 0.037 (7) | 0.009 (4) | −0.009 (5) | 0.013 (4) |
C8 | 0.029 (4) | 0.037 (5) | 0.022 (4) | −0.004 (3) | −0.003 (3) | 0.000 (3) |
C16 | 0.018 (3) | 0.033 (4) | 0.031 (4) | 0.000 (3) | −0.002 (3) | 0.007 (3) |
C10 | 0.016 (4) | 0.029 (4) | 0.021 (4) | −0.001 (3) | −0.001 (3) | 0.009 (3) |
C15 | 0.027 (4) | 0.029 (4) | 0.020 (4) | 0.004 (4) | 0.006 (3) | −0.002 (4) |
C11 | 0.023 (4) | 0.022 (4) | 0.022 (4) | −0.001 (3) | −0.004 (3) | 0.003 (3) |
C29 | 0.043 (5) | 0.026 (4) | 0.046 (6) | 0.010 (5) | −0.017 (4) | −0.005 (5) |
C4 | 0.025 (4) | 0.032 (4) | 0.021 (4) | 0.008 (4) | 0.010 (3) | −0.010 (4) |
C19 | 0.027 (4) | 0.024 (4) | 0.026 (4) | 0.002 (3) | −0.005 (3) | −0.006 (3) |
C22 | 0.026 (4) | 0.028 (4) | 0.023 (4) | 0.008 (3) | −0.007 (4) | −0.003 (3) |
C17 | 0.022 (4) | 0.032 (4) | 0.024 (4) | 0.001 (3) | 0.001 (3) | −0.005 (3) |
C23 | 0.020 (3) | 0.035 (4) | 0.028 (4) | −0.003 (3) | 0.005 (3) | −0.008 (3) |
C32 | 0.050 (9) | 0.073 (10) | 0.030 (7) | 0.007 (5) | −0.008 (6) | −0.001 (5) |
C12 | 0.019 (4) | 0.032 (4) | 0.020 (4) | −0.001 (3) | −0.005 (3) | 0.004 (3) |
C28 | 0.036 (4) | 0.036 (4) | 0.022 (4) | −0.002 (3) | −0.008 (4) | 0.007 (3) |
C9 | 0.021 (4) | 0.039 (5) | 0.028 (5) | 0.000 (3) | −0.004 (3) | 0.004 (4) |
C18 | 0.017 (3) | 0.031 (4) | 0.020 (4) | 0.005 (3) | −0.001 (3) | −0.006 (3) |
C20 | 0.022 (4) | 0.034 (5) | 0.026 (5) | 0.004 (3) | −0.003 (3) | −0.004 (4) |
C7 | 0.031 (4) | 0.023 (4) | 0.020 (3) | 0.004 (3) | 0.001 (3) | 0.001 (3) |
C21 | 0.025 (4) | 0.036 (5) | 0.027 (4) | 0.002 (3) | −0.007 (3) | −0.003 (3) |
C5 | 0.032 (4) | 0.031 (4) | 0.033 (4) | 0.002 (3) | 0.004 (4) | −0.004 (4) |
C13 | 0.020 (3) | 0.033 (4) | 0.032 (4) | −0.002 (3) | −0.003 (3) | 0.006 (3) |
C26 | 0.024 (4) | 0.031 (4) | 0.027 (4) | 0.001 (3) | −0.005 (3) | −0.004 (3) |
C31 | 0.037 (4) | 0.028 (5) | 0.035 (5) | −0.003 (3) | −0.007 (4) | 0.001 (3) |
C2 | 0.033 (4) | 0.045 (6) | 0.030 (5) | 0.003 (3) | 0.003 (3) | −0.003 (4) |
C1 | 0.035 (7) | 0.021 (7) | 0.043 (8) | −0.001 (3) | 0.011 (6) | −0.005 (3) |
Br1—C15 | 1.887 (7) | C29—H29A | 0.9700 |
Br2—C24 | 1.907 (8) | C29—H29B | 0.9700 |
C25—C26 | 1.393 (12) | C4—C5 | 1.491 (11) |
C25—C24 | 1.421 (10) | C4—H4A | 0.9700 |
C25—H25A | 0.9300 | C4—H4B | 0.9700 |
O1—C7 | 1.377 (8) | C19—C20 | 1.420 (9) |
O1—C6 | 1.406 (12) | C19—C23 | 1.422 (9) |
O2—C22 | 1.363 (8) | C19—C18 | 1.438 (9) |
O2—C27 | 1.491 (14) | C22—C17 | 1.388 (9) |
C30—C29 | 1.470 (14) | C22—C21 | 1.420 (11) |
C30—C31 | 1.522 (12) | C17—C18 | 1.427 (9) |
C30—H30A | 0.9700 | C17—C12 | 1.503 (6) |
C30—H30B | 0.9700 | C23—H23A | 0.9300 |
C14—C13 | 1.349 (11) | C32—C31 | 1.501 (15) |
C14—C15 | 1.408 (10) | C32—H32A | 0.9600 |
C14—H14A | 0.9300 | C32—H32B | 0.9600 |
C3—C2 | 1.510 (11) | C32—H32C | 0.9600 |
C3—C4 | 1.550 (12) | C12—C7 | 1.393 (9) |
C3—H3A | 0.9700 | C28—H28A | 0.9700 |
C3—H3B | 0.9700 | C28—H28B | 0.9700 |
C6—C5 | 1.524 (12) | C9—H9A | 0.9300 |
C6—H6A | 0.9700 | C18—C26 | 1.415 (9) |
C6—H6B | 0.9700 | C20—C21 | 1.368 (10) |
C24—C23 | 1.342 (10) | C20—H20A | 0.9300 |
C27—C28 | 1.485 (14) | C21—H21A | 0.9300 |
C27—H27A | 0.9700 | C5—H5A | 0.9700 |
C27—H27B | 0.9700 | C5—H5B | 0.9700 |
C8—C9 | 1.368 (10) | C13—H13A | 0.9300 |
C8—C7 | 1.404 (11) | C26—H26A | 0.9300 |
C8—H8A | 0.9300 | C31—H31A | 0.9700 |
C16—C15 | 1.364 (10) | C31—H31B | 0.9700 |
C16—C10 | 1.419 (10) | C2—C1 | 1.554 (14) |
C16—H16A | 0.9300 | C2—H2A | 0.9700 |
C10—C9 | 1.417 (9) | C2—H2B | 0.9700 |
C10—C11 | 1.420 (9) | C1—H1A | 0.9600 |
C11—C12 | 1.423 (9) | C1—H1B | 0.9600 |
C11—C13 | 1.427 (9) | C1—H1C | 0.9600 |
C29—C28 | 1.546 (11) | ||
C26—C25—C24 | 116.8 (8) | C17—C22—C21 | 121.0 (6) |
C26—C25—H25A | 121.6 | C22—C17—C18 | 119.6 (6) |
C24—C25—H25A | 121.6 | C22—C17—C12 | 120.5 (6) |
C7—O1—C6 | 117.6 (6) | C18—C17—C12 | 119.9 (6) |
C22—O2—C27 | 119.2 (7) | C24—C23—C19 | 120.5 (7) |
C29—C30—C31 | 113.6 (8) | C24—C23—H23A | 119.7 |
C29—C30—H30A | 108.8 | C19—C23—H23A | 119.7 |
C31—C30—H30A | 108.8 | C31—C32—H32A | 109.5 |
C29—C30—H30B | 108.8 | C31—C32—H32B | 109.5 |
C31—C30—H30B | 108.8 | H32A—C32—H32B | 109.5 |
H30A—C30—H30B | 107.7 | C31—C32—H32C | 109.5 |
C13—C14—C15 | 120.0 (8) | H32A—C32—H32C | 109.5 |
C13—C14—H14A | 120.0 | H32B—C32—H32C | 109.5 |
C15—C14—H14A | 120.0 | C7—C12—C11 | 118.3 (6) |
C2—C3—C4 | 114.5 (8) | C7—C12—C17 | 120.3 (6) |
C2—C3—H3A | 108.6 | C11—C12—C17 | 121.4 (6) |
C4—C3—H3A | 108.6 | C27—C28—C29 | 115.2 (7) |
C2—C3—H3B | 108.6 | C27—C28—H28A | 108.5 |
C4—C3—H3B | 108.6 | C29—C28—H28A | 108.5 |
H3A—C3—H3B | 107.6 | C27—C28—H28B | 108.5 |
O1—C6—C5 | 109.2 (8) | C29—C28—H28B | 108.5 |
O1—C6—H6A | 109.8 | H28A—C28—H28B | 107.5 |
C5—C6—H6A | 109.8 | C8—C9—C10 | 120.8 (7) |
O1—C6—H6B | 109.8 | C8—C9—H9A | 119.6 |
C5—C6—H6B | 109.8 | C10—C9—H9A | 119.6 |
H6A—C6—H6B | 108.3 | C26—C18—C17 | 123.0 (6) |
C23—C24—C25 | 122.8 (8) | C26—C18—C19 | 117.2 (7) |
C23—C24—Br2 | 121.4 (5) | C17—C18—C19 | 119.8 (6) |
C25—C24—Br2 | 115.8 (6) | C21—C20—C19 | 122.3 (7) |
O2—C27—C28 | 107.0 (9) | C21—C20—H20A | 118.8 |
O2—C27—H27A | 110.3 | C19—C20—H20A | 118.8 |
C28—C27—H27A | 110.3 | O1—C7—C12 | 115.9 (6) |
O2—C27—H27B | 110.3 | O1—C7—C8 | 123.1 (6) |
C28—C27—H27B | 110.3 | C12—C7—C8 | 120.9 (6) |
H27A—C27—H27B | 108.6 | C20—C21—C22 | 119.5 (7) |
C9—C8—C7 | 120.8 (7) | C20—C21—H21A | 120.2 |
C9—C8—H8A | 119.6 | C22—C21—H21A | 120.2 |
C7—C8—H8A | 119.6 | C4—C5—C6 | 113.7 (6) |
C15—C16—C10 | 119.8 (6) | C4—C5—H5A | 108.8 |
C15—C16—H16A | 120.1 | C6—C5—H5A | 108.8 |
C10—C16—H16A | 120.1 | C4—C5—H5B | 108.8 |
C9—C10—C16 | 122.0 (6) | C6—C5—H5B | 108.8 |
C9—C10—C11 | 118.2 (7) | H5A—C5—H5B | 107.7 |
C16—C10—C11 | 119.7 (6) | C14—C13—C11 | 121.7 (7) |
C16—C15—C14 | 121.0 (7) | C14—C13—H13A | 119.2 |
C16—C15—Br1 | 119.9 (5) | C11—C13—H13A | 119.2 |
C14—C15—Br1 | 119.1 (6) | C25—C26—C18 | 123.1 (7) |
C10—C11—C12 | 120.9 (6) | C25—C26—H26A | 118.5 |
C10—C11—C13 | 117.6 (7) | C18—C26—H26A | 118.5 |
C12—C11—C13 | 121.5 (6) | C32—C31—C30 | 110.8 (8) |
C30—C29—C28 | 112.6 (8) | C32—C31—H31A | 109.5 |
C30—C29—H29A | 109.1 | C30—C31—H31A | 109.5 |
C28—C29—H29A | 109.1 | C32—C31—H31B | 109.5 |
C30—C29—H29B | 109.1 | C30—C31—H31B | 109.5 |
C28—C29—H29B | 109.1 | H31A—C31—H31B | 108.1 |
H29A—C29—H29B | 107.8 | C3—C2—C1 | 112.7 (7) |
C5—C4—C3 | 113.8 (7) | C3—C2—H2A | 109.0 |
C5—C4—H4A | 108.8 | C1—C2—H2A | 109.0 |
C3—C4—H4A | 108.8 | C3—C2—H2B | 109.0 |
C5—C4—H4B | 108.8 | C1—C2—H2B | 109.0 |
C3—C4—H4B | 108.8 | H2A—C2—H2B | 107.8 |
H4A—C4—H4B | 107.7 | C2—C1—H1A | 109.5 |
C20—C19—C23 | 123.0 (6) | C2—C1—H1B | 109.5 |
C20—C19—C18 | 117.7 (7) | H1A—C1—H1B | 109.5 |
C23—C19—C18 | 119.2 (7) | C2—C1—H1C | 109.5 |
O2—C22—C17 | 116.4 (6) | H1A—C1—H1C | 109.5 |
O2—C22—C21 | 122.6 (6) | H1B—C1—H1C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C32H36Br2O2 |
Mr | 612.43 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 293 |
a, b, c (Å) | 12.401 (3), 8.1742 (16), 27.396 (6) |
V (Å3) | 2777.1 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.95 |
Crystal size (mm) | 0.25 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26425, 3647, 3581 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.103, 0.91 |
No. of reflections | 3647 |
No. of parameters | 325 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.53, −0.38 |
Absolute structure | Flack (1983), 2766 Freidel pairs |
Absolute structure parameter | 0.49 (2) |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
6,6'-Dibromo-1,1'-bi-2-naphthol derivatives have received considerable attention in the literature. They are attractive from several points of view in application (Hu et al., 1996). As part of our search for new 6,6'-dibromo-1,1'-bi-2-naphthol compounds we synthesized the title compound (I), and describe its structure here. The angle between the planes of the naphthalene rings is 60.1 (6)°.
The C17—C12 bond length of 1.504 (6)Å is comparable with C—C single bond [1.532 (4) Å] reported (van Nes et al., 1978). In the structure, there is no classcical hydrogen bonds. The crystal structure is stabilized by weak π-π interactions involving the six-membered rings (Cg1: C7-C12) and (Cg4î: C18-C26) [ (i) 1/2 + x, 3/2 - y, z], and the other six-membered six-membered rings (Cg2: C10-C16) and (Cg3î: C17-C22) rings, with centroid-centroid distances of 4.012 (4) \%A and 4.010 (4) Å, respectively.