Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028321/ci6633sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028321/ci6633Isup2.hkl |
CCDC reference: 287506
Key indicators
- Single-crystal X-ray study
- T = 122 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.081
- Data-to-parameter ratio = 31.0
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.87 Ratio
Author Response: The large range in the Ueq(max)/Ueq(min) value is reasonable for this tructure because it is the peripheral carbon atoms which have the large values. |
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.21 Ratio
Author Response: The large range in the Ueq(max)/Ueq(min) value is reasonable for this tructure because it is the peripheral carbon atoms which have the large values. |
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.00 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13A PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 40
Alert level G ABSTY01_ALERT_1_G Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
1-Bromo-3,4-bis(bromomethyl)-2,5-dimethoxybenzene (50 g, 0.12 mol), prepared as described by Hammershøj et al. (2005), was dissolved in dried tetrahydrofuran (800 ml) and NaH (80% suspension in oil, 14 g) was added. The reaction mixture was stirred under an N2 atmosphere for 10 min at room temperature. Diethylmalonate (20 g, 0.2 mol) was dissolved in dried tetrahydrofuran (200 ml) and added over a 50 min period under an N2 atmosphere. After 2 h, brine (800 ml) was added and the mixture was extracted with diethyl ether (3 × 200 ml). The combined organic extracts were dried with MgSO4 and evaporated to dryness in vacuo yielding a pale green oil. Purification by crystallization in methanol yielded compound (I) as a white powder (30.2 g, 60%; m.p. 359–361 K); 1H NMR (300 MHz, CDCl3): δ 6.6 (1H, s), 4.15 (4H, s, J 7.14 Hz), 3.72 (3H, s), 3.7 (3H, s), 3.5 (2H, s), 3.4 (2H, s), 1.2 (6H, t); 13C NMR (100 MHz, CDCl3): δ 170.2, 151.1, 145.9, 134.0, 128.1, 113.6, 112.8, 60.8, 59.4, 54.7, 37.4, 36.6, 12.9; m/e: 402 (71), 328 (100), 253 (94), 69(59.5) and 32 (87.5%); analysis calculated for C17H21BrO6: C 50.89, H 5.28%; found: C 51.03, H 5.27%. [Omit 13C NMR from publication due to lack of assignments?]
H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H = 0.95–0.99 Å and Uiso(H) = 1.2–1.5Ueq(C).
Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
C17H21BrO6 | Z = 4 |
Mr = 401.24 | F(000) = 824 |
Triclinic, P1 | Dx = 1.481 Mg m−3 |
Hall symbol: -P 1 | Melting point = 86–88 K |
a = 11.1440 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1630 (7) Å | Cell parameters from 45017 reflections |
c = 15.7690 (14) Å | θ = 1.4–33.0° |
α = 75.782 (5)° | µ = 2.31 mm−1 |
β = 77.534 (7)° | T = 122 K |
γ = 73.395 (5)° | Prism, white |
V = 1799.7 (2) Å3 | 0.59 × 0.34 × 0.19 mm |
Nonius KappaCCD area-detector diffractometer | 13426 independent reflections |
Radiation source: fine-focus sealed tube | 11251 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω and ϕ scans | θmax = 33.0°, θmin = 1.4° |
Absorption correction: gaussian integration (Coppens, 1970) | h = −17→17 |
Tmin = 0.427, Tmax = 0.768 | k = −17→16 |
72293 measured reflections | l = −24→24 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0247P)2 + 1.4569P] where P = (Fo2 + 2Fc2)/3 |
13426 reflections | (Δ/σ)max = 0.002 |
433 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.65 e Å−3 |
C17H21BrO6 | γ = 73.395 (5)° |
Mr = 401.24 | V = 1799.7 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.1440 (8) Å | Mo Kα radiation |
b = 11.1630 (7) Å | µ = 2.31 mm−1 |
c = 15.7690 (14) Å | T = 122 K |
α = 75.782 (5)° | 0.59 × 0.34 × 0.19 mm |
β = 77.534 (7)° |
Nonius KappaCCD area-detector diffractometer | 13426 independent reflections |
Absorption correction: gaussian integration (Coppens, 1970) | 11251 reflections with I > 2σ(I) |
Tmin = 0.427, Tmax = 0.768 | Rint = 0.042 |
72293 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.60 e Å−3 |
13426 reflections | Δρmin = −0.65 e Å−3 |
433 parameters |
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 | ||
Br1B | 0.369897 (13) | 0.418763 (14) | −0.024836 (10) | 0.01906 (4) | |
Br1A | 0.619151 (16) | 0.150871 (17) | 0.464061 (13) | 0.02890 (5) | |
O4B | −0.36276 (9) | 0.92325 (10) | −0.06419 (7) | 0.01613 (19) | |
O3A | −0.02489 (10) | 0.71534 (11) | 0.33896 (7) | 0.0192 (2) | |
O3B | −0.22685 (10) | 0.81749 (10) | −0.16557 (7) | 0.01681 (19) | |
O1A | 0.42439 (11) | 0.30944 (11) | 0.34134 (7) | 0.0202 (2) | |
O5B | −0.18508 (12) | 1.05739 (11) | 0.01939 (7) | 0.0214 (2) | |
O6B | −0.17127 (10) | 1.09389 (9) | −0.12922 (6) | 0.01437 (18) | |
O1B | 0.24196 (10) | 0.65731 (10) | −0.15150 (7) | 0.01521 (18) | |
O2A | 0.33824 (10) | 0.49569 (10) | 0.65124 (7) | 0.0172 (2) | |
C8B | −0.14590 (12) | 0.88055 (12) | −0.05577 (8) | 0.0112 (2) | |
O2B | −0.07670 (10) | 0.56274 (10) | 0.16846 (6) | 0.01503 (18) | |
C1A | 0.36762 (13) | 0.44428 (13) | 0.57708 (9) | 0.0127 (2) | |
C7A | 0.17528 (14) | 0.61475 (14) | 0.51764 (9) | 0.0162 (2) | |
H7AA | 0.1958 | 0.6863 | 0.5335 | 0.019* | |
H7AB | 0.1044 | 0.5895 | 0.5617 | 0.019* | |
C12B | −0.24713 (12) | 0.86930 (12) | −0.10343 (9) | 0.0119 (2) | |
C2A | 0.46651 (13) | 0.33836 (13) | 0.56252 (9) | 0.0150 (2) | |
H2A | 0.5214 | 0.2968 | 0.6051 | 0.018* | |
C6B | −0.02936 (12) | 0.68863 (12) | 0.02915 (8) | 0.0110 (2) | |
C1B | 0.00871 (12) | 0.58008 (12) | 0.09288 (8) | 0.0112 (2) | |
O6A | 0.11175 (10) | 0.87541 (10) | 0.39525 (7) | 0.01708 (19) | |
O5A | 0.28954 (10) | 0.76599 (11) | 0.32194 (7) | 0.0197 (2) | |
C5B | 0.04917 (12) | 0.71517 (12) | −0.05050 (8) | 0.0106 (2) | |
C8A | 0.14155 (13) | 0.65201 (13) | 0.42213 (9) | 0.0131 (2) | |
C13B | −0.47135 (14) | 0.92250 (15) | −0.10169 (10) | 0.0194 (3) | |
H13BA | −0.5437 | 0.9132 | −0.0537 | 0.023* | |
H13BB | −0.4495 | 0.8491 | −0.1317 | 0.023* | |
C4B | 0.16913 (12) | 0.63488 (12) | −0.06958 (8) | 0.0117 (2) | |
C2B | 0.12871 (13) | 0.49928 (13) | 0.07637 (9) | 0.0130 (2) | |
H2B | 0.1572 | 0.4257 | 0.1192 | 0.016* | |
C5A | 0.30858 (13) | 0.45844 (13) | 0.43537 (9) | 0.0129 (2) | |
C9B | −0.00974 (12) | 0.83843 (13) | −0.10749 (9) | 0.0129 (2) | |
H9BA | −0.0132 | 0.8253 | −0.1667 | 0.015* | |
H9BB | 0.0388 | 0.9030 | −0.1148 | 0.015* | |
C7B | −0.15124 (13) | 0.79013 (13) | 0.03702 (9) | 0.0137 (2) | |
H7BA | −0.1558 | 0.8363 | 0.0842 | 0.016* | |
H7BB | −0.2254 | 0.7528 | 0.0501 | 0.016* | |
C12A | −0.00118 (13) | 0.68641 (13) | 0.42253 (9) | 0.0153 (2) | |
C3B | 0.20644 (12) | 0.52853 (13) | −0.00446 (9) | 0.0127 (2) | |
C4A | 0.40568 (13) | 0.35182 (13) | 0.41946 (9) | 0.0147 (2) | |
O4A | −0.08100 (11) | 0.68666 (13) | 0.48731 (8) | 0.0273 (3) | |
C3A | 0.48342 (13) | 0.29438 (13) | 0.48379 (10) | 0.0160 (2) | |
C15B | −0.17139 (12) | 1.01968 (13) | −0.04831 (9) | 0.0126 (2) | |
C6A | 0.28934 (12) | 0.50391 (13) | 0.51267 (8) | 0.0123 (2) | |
C9A | 0.21017 (14) | 0.53489 (14) | 0.37772 (9) | 0.0157 (2) | |
H9AA | 0.1501 | 0.4848 | 0.3771 | 0.019* | |
H9AB | 0.2504 | 0.5622 | 0.3162 | 0.019* | |
C16B | −0.18867 (14) | 1.23033 (13) | −0.13404 (10) | 0.0156 (2) | |
H16BA | −0.1487 | 1.2687 | −0.1929 | 0.019* | |
H16BB | −0.1465 | 1.2424 | −0.0886 | 0.019* | |
C15A | 0.19117 (13) | 0.76898 (13) | 0.37282 (9) | 0.0140 (2) | |
C16A | 0.14748 (16) | 0.99388 (14) | 0.35006 (11) | 0.0213 (3) | |
H16AA | 0.1609 | 1.0007 | 0.2851 | 0.026* | |
H16AB | 0.2272 | 0.9958 | 0.3672 | 0.026* | |
C10A | 0.41040 (15) | 0.43277 (16) | 0.72134 (10) | 0.0210 (3) | |
H10AA | 0.3804 | 0.4792 | 0.7702 | 0.025* | |
H10AB | 0.5002 | 0.4304 | 0.6995 | 0.025* | |
H10AC | 0.4001 | 0.3455 | 0.7424 | 0.025* | |
C10B | −0.04076 (15) | 0.45055 (14) | 0.23398 (9) | 0.0185 (3) | |
H10BA | −0.1089 | 0.4489 | 0.2850 | 0.022* | |
H10BB | 0.0370 | 0.4513 | 0.2531 | 0.022* | |
H10BC | −0.0258 | 0.3747 | 0.2086 | 0.022* | |
C11B | 0.33152 (16) | 0.73108 (16) | −0.15717 (11) | 0.0241 (3) | |
H11BA | 0.3792 | 0.7424 | −0.2174 | 0.029* | |
H11BB | 0.3903 | 0.6863 | −0.1149 | 0.029* | |
H11BC | 0.2860 | 0.8147 | −0.1431 | 0.029* | |
C17B | −0.32748 (15) | 1.29643 (15) | −0.11915 (11) | 0.0210 (3) | |
H17BA | −0.3371 | 1.3875 | −0.1226 | 0.025* | |
H17BB | −0.3668 | 1.2592 | −0.0605 | 0.025* | |
H17BC | −0.3689 | 1.2856 | −0.1647 | 0.025* | |
C13A | −0.15783 (15) | 0.76139 (17) | 0.32701 (12) | 0.0238 (3) | |
H13AA | −0.2109 | 0.7190 | 0.3776 | 0.029* | |
H13AB | −0.1688 | 0.7403 | 0.2722 | 0.029* | |
C11A | 0.35392 (19) | 0.2173 (2) | 0.34724 (13) | 0.0322 (4) | |
H11AA | 0.3707 | 0.1901 | 0.2903 | 0.039* | |
H11AB | 0.2631 | 0.2557 | 0.3617 | 0.039* | |
H11AC | 0.3799 | 0.1432 | 0.3937 | 0.039* | |
C17A | 0.0414 (2) | 1.10264 (16) | 0.37687 (13) | 0.0305 (4) | |
H17AA | 0.0629 | 1.1836 | 0.3474 | 0.037* | |
H17AB | 0.0292 | 1.0951 | 0.4412 | 0.037* | |
H17AC | −0.0369 | 1.1000 | 0.3594 | 0.037* | |
C14B | −0.50813 (18) | 1.0445 (2) | −0.16707 (14) | 0.0340 (4) | |
H14BA | −0.5808 | 1.0430 | −0.1921 | 0.041* | |
H14BB | −0.4365 | 1.0531 | −0.2147 | 0.041* | |
H14BC | −0.5310 | 1.1168 | −0.1370 | 0.041* | |
C14A | −0.1991 (3) | 0.9023 (2) | 0.3211 (2) | 0.0600 (8) | |
H14AA | −0.2883 | 0.9328 | 0.3130 | 0.072* | |
H14AB | −0.1469 | 0.9440 | 0.2707 | 0.072* | |
H14AC | −0.1891 | 0.9227 | 0.3758 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1B | 0.01267 (6) | 0.01661 (7) | 0.02272 (7) | 0.00240 (5) | −0.00023 (5) | −0.00366 (5) |
Br1A | 0.02201 (8) | 0.02654 (9) | 0.03630 (9) | 0.00841 (6) | −0.00793 (7) | −0.01680 (7) |
O4B | 0.0109 (4) | 0.0202 (5) | 0.0180 (5) | −0.0007 (4) | −0.0031 (3) | −0.0079 (4) |
O3A | 0.0146 (5) | 0.0253 (5) | 0.0161 (5) | −0.0021 (4) | −0.0042 (4) | −0.0030 (4) |
O3B | 0.0196 (5) | 0.0174 (5) | 0.0150 (4) | −0.0044 (4) | −0.0026 (4) | −0.0063 (4) |
O1A | 0.0216 (5) | 0.0236 (5) | 0.0171 (5) | −0.0049 (4) | 0.0010 (4) | −0.0117 (4) |
O5B | 0.0325 (6) | 0.0178 (5) | 0.0152 (5) | −0.0048 (4) | −0.0046 (4) | −0.0063 (4) |
O6B | 0.0190 (5) | 0.0103 (4) | 0.0129 (4) | −0.0018 (3) | −0.0033 (3) | −0.0023 (3) |
O1B | 0.0137 (4) | 0.0181 (5) | 0.0129 (4) | −0.0048 (4) | 0.0030 (3) | −0.0050 (4) |
O2A | 0.0175 (5) | 0.0206 (5) | 0.0111 (4) | 0.0012 (4) | −0.0034 (4) | −0.0045 (4) |
C8B | 0.0108 (5) | 0.0112 (5) | 0.0107 (5) | −0.0011 (4) | −0.0019 (4) | −0.0020 (4) |
O2B | 0.0146 (4) | 0.0151 (4) | 0.0108 (4) | −0.0012 (4) | 0.0012 (3) | 0.0001 (3) |
C1A | 0.0128 (5) | 0.0139 (6) | 0.0108 (5) | −0.0037 (4) | −0.0003 (4) | −0.0021 (4) |
C7A | 0.0191 (6) | 0.0161 (6) | 0.0102 (5) | 0.0012 (5) | −0.0020 (5) | −0.0035 (5) |
C12B | 0.0125 (5) | 0.0092 (5) | 0.0129 (5) | −0.0021 (4) | −0.0025 (4) | −0.0002 (4) |
C2A | 0.0119 (5) | 0.0158 (6) | 0.0165 (6) | −0.0016 (5) | −0.0022 (4) | −0.0035 (5) |
C6B | 0.0097 (5) | 0.0115 (5) | 0.0117 (5) | −0.0019 (4) | −0.0014 (4) | −0.0033 (4) |
C1B | 0.0115 (5) | 0.0114 (5) | 0.0109 (5) | −0.0029 (4) | −0.0008 (4) | −0.0032 (4) |
O6A | 0.0183 (5) | 0.0132 (4) | 0.0172 (5) | −0.0047 (4) | 0.0021 (4) | −0.0016 (4) |
O5A | 0.0138 (4) | 0.0237 (5) | 0.0189 (5) | −0.0046 (4) | 0.0013 (4) | −0.0025 (4) |
C5B | 0.0104 (5) | 0.0106 (5) | 0.0111 (5) | −0.0026 (4) | −0.0012 (4) | −0.0029 (4) |
C8A | 0.0131 (5) | 0.0134 (6) | 0.0112 (5) | −0.0019 (4) | −0.0010 (4) | −0.0018 (4) |
C13B | 0.0128 (6) | 0.0233 (7) | 0.0240 (7) | −0.0049 (5) | −0.0053 (5) | −0.0052 (6) |
C4B | 0.0110 (5) | 0.0121 (5) | 0.0118 (5) | −0.0026 (4) | 0.0001 (4) | −0.0035 (4) |
C2B | 0.0129 (5) | 0.0113 (5) | 0.0137 (5) | −0.0018 (4) | −0.0021 (4) | −0.0021 (4) |
C5A | 0.0138 (5) | 0.0130 (6) | 0.0113 (5) | −0.0039 (4) | −0.0003 (4) | −0.0019 (4) |
C9B | 0.0116 (5) | 0.0125 (5) | 0.0113 (5) | −0.0008 (4) | 0.0003 (4) | −0.0007 (4) |
C7B | 0.0116 (5) | 0.0143 (6) | 0.0112 (5) | 0.0002 (4) | 0.0004 (4) | −0.0011 (4) |
C12A | 0.0154 (6) | 0.0139 (6) | 0.0162 (6) | −0.0049 (5) | −0.0018 (5) | −0.0015 (5) |
C3B | 0.0096 (5) | 0.0111 (5) | 0.0161 (6) | −0.0004 (4) | −0.0011 (4) | −0.0038 (4) |
C4A | 0.0138 (6) | 0.0162 (6) | 0.0145 (6) | −0.0039 (5) | 0.0006 (4) | −0.0061 (5) |
O4A | 0.0180 (5) | 0.0414 (7) | 0.0196 (5) | −0.0100 (5) | 0.0031 (4) | −0.0027 (5) |
C3A | 0.0120 (5) | 0.0144 (6) | 0.0207 (6) | −0.0008 (5) | −0.0009 (5) | −0.0064 (5) |
C15B | 0.0104 (5) | 0.0132 (6) | 0.0137 (5) | −0.0015 (4) | −0.0022 (4) | −0.0031 (4) |
C6A | 0.0127 (5) | 0.0118 (5) | 0.0109 (5) | −0.0027 (4) | −0.0005 (4) | −0.0012 (4) |
C9A | 0.0188 (6) | 0.0160 (6) | 0.0118 (5) | −0.0020 (5) | −0.0030 (5) | −0.0041 (5) |
C16B | 0.0175 (6) | 0.0109 (5) | 0.0185 (6) | −0.0039 (5) | −0.0034 (5) | −0.0021 (5) |
C15A | 0.0131 (5) | 0.0162 (6) | 0.0121 (5) | −0.0025 (5) | −0.0040 (4) | −0.0016 (4) |
C16A | 0.0249 (7) | 0.0148 (6) | 0.0226 (7) | −0.0089 (5) | −0.0005 (6) | 0.0015 (5) |
C10A | 0.0225 (7) | 0.0256 (7) | 0.0137 (6) | −0.0006 (6) | −0.0067 (5) | −0.0044 (5) |
C10B | 0.0207 (6) | 0.0192 (7) | 0.0115 (6) | −0.0031 (5) | −0.0014 (5) | 0.0015 (5) |
C11B | 0.0230 (7) | 0.0251 (8) | 0.0245 (7) | −0.0134 (6) | 0.0095 (6) | −0.0084 (6) |
C17B | 0.0193 (7) | 0.0161 (6) | 0.0240 (7) | 0.0008 (5) | −0.0023 (5) | −0.0044 (5) |
C13A | 0.0162 (6) | 0.0285 (8) | 0.0291 (8) | −0.0032 (6) | −0.0096 (6) | −0.0074 (6) |
C11A | 0.0347 (9) | 0.0370 (10) | 0.0347 (9) | −0.0137 (8) | −0.0025 (7) | −0.0219 (8) |
C17A | 0.0404 (10) | 0.0156 (7) | 0.0302 (8) | −0.0058 (7) | 0.0028 (7) | −0.0035 (6) |
C14B | 0.0254 (8) | 0.0381 (10) | 0.0362 (10) | −0.0069 (7) | −0.0162 (7) | 0.0058 (8) |
C14A | 0.0493 (14) | 0.0354 (12) | 0.101 (2) | 0.0145 (10) | −0.0494 (15) | −0.0210 (13) |
Br1B—C3B | 1.8941 (13) | C2B—C3B | 1.4008 (18) |
Br1A—C3A | 1.8994 (14) | C2B—H2B | 0.95 |
O4B—C12B | 1.3421 (16) | C5A—C6A | 1.3850 (18) |
O4B—C13B | 1.4599 (17) | C5A—C4A | 1.3943 (19) |
O3A—C12A | 1.3428 (17) | C5A—C9A | 1.5072 (19) |
O3A—C13A | 1.4602 (18) | C9B—H9BA | 0.99 |
O3B—C12B | 1.2057 (16) | C9B—H9BB | 0.99 |
O1A—C4A | 1.3798 (17) | C7B—H7BA | 0.99 |
O1A—C11A | 1.438 (2) | C7B—H7BB | 0.99 |
O5B—C15B | 1.2058 (17) | C12A—O4A | 1.2011 (18) |
O6B—C15B | 1.3397 (16) | C4A—C3A | 1.390 (2) |
O6B—C16B | 1.4642 (17) | C9A—H9AA | 0.99 |
O1B—C4B | 1.3764 (16) | C9A—H9AB | 0.99 |
O1B—C11B | 1.4413 (18) | C16B—C17B | 1.506 (2) |
O2A—C1A | 1.3642 (16) | C16B—H16BA | 0.99 |
O2A—C10A | 1.4287 (18) | C16B—H16BB | 0.99 |
C8B—C15B | 1.5263 (19) | C16A—C17A | 1.505 (2) |
C8B—C12B | 1.5320 (18) | C16A—H16AA | 0.99 |
C8B—C7B | 1.5603 (18) | C16A—H16AB | 0.99 |
C8B—C9B | 1.5604 (18) | C10A—H10AA | 0.98 |
O2B—C1B | 1.3660 (16) | C10A—H10AB | 0.98 |
O2B—C10B | 1.4327 (17) | C10A—H10AC | 0.98 |
C1A—C2A | 1.3945 (19) | C10B—H10BA | 0.98 |
C1A—C6A | 1.3980 (19) | C10B—H10BB | 0.98 |
C7A—C6A | 1.5028 (19) | C10B—H10BC | 0.98 |
C7A—C8A | 1.5588 (19) | C11B—H11BA | 0.98 |
C7A—H7AA | 0.99 | C11B—H11BB | 0.98 |
C7A—H7AB | 0.99 | C11B—H11BC | 0.98 |
C2A—C3A | 1.401 (2) | C17B—H17BA | 0.98 |
C2A—H2A | 0.95 | C17B—H17BB | 0.98 |
C6B—C5B | 1.3864 (17) | C17B—H17BC | 0.98 |
C6B—C1B | 1.3965 (18) | C13A—C14A | 1.493 (3) |
C6B—C7B | 1.5036 (18) | C13A—H13AA | 0.99 |
C1B—C2B | 1.3947 (18) | C13A—H13AB | 0.99 |
O6A—C15A | 1.3380 (17) | C11A—H11AA | 0.98 |
O6A—C16A | 1.4597 (18) | C11A—H11AB | 0.98 |
O5A—C15A | 1.2080 (17) | C11A—H11AC | 0.98 |
C5B—C4B | 1.3982 (17) | C17A—H17AA | 0.98 |
C5B—C9B | 1.5043 (18) | C17A—H17AB | 0.98 |
C8A—C12A | 1.5249 (19) | C17A—H17AC | 0.98 |
C8A—C15A | 1.5308 (19) | C14B—H14BA | 0.98 |
C8A—C9A | 1.5594 (19) | C14B—H14BB | 0.98 |
C13B—C14B | 1.503 (2) | C14B—H14BC | 0.98 |
C13B—H13BA | 0.99 | C14A—H14AA | 0.98 |
C13B—H13BB | 0.99 | C14A—H14AB | 0.98 |
C4B—C3B | 1.3929 (18) | C14A—H14AC | 0.98 |
C12B—O4B—C13B | 117.25 (11) | C2A—C3A—Br1A | 118.44 (11) |
C12A—O3A—C13A | 116.70 (12) | O5B—C15B—O6B | 124.80 (13) |
C4A—O1A—C11A | 112.74 (12) | O5B—C15B—C8B | 125.58 (12) |
C15B—O6B—C16B | 116.45 (11) | O6B—C15B—C8B | 109.57 (11) |
C4B—O1B—C11B | 114.84 (11) | C5A—C6A—C1A | 120.77 (12) |
C1A—O2A—C10A | 117.59 (11) | C5A—C6A—C7A | 111.95 (12) |
C15B—C8B—C12B | 108.10 (10) | C1A—C6A—C7A | 127.22 (12) |
C15B—C8B—C7B | 111.82 (11) | C5A—C9A—C8A | 103.80 (11) |
C12B—C8B—C7B | 109.14 (11) | C5A—C9A—H9AA | 111.0 |
C15B—C8B—C9B | 109.16 (11) | C8A—C9A—H9AA | 111.0 |
C12B—C8B—C9B | 111.55 (10) | C5A—C9A—H9AB | 111.0 |
C7B—C8B—C9B | 107.10 (10) | C8A—C9A—H9AB | 111.0 |
C1B—O2B—C10B | 116.92 (11) | H9AA—C9A—H9AB | 109.0 |
O2A—C1A—C2A | 125.11 (12) | O6B—C16B—C17B | 110.76 (12) |
O2A—C1A—C6A | 115.66 (12) | O6B—C16B—H16BA | 109.5 |
C2A—C1A—C6A | 119.22 (12) | C17B—C16B—H16BA | 109.5 |
C6A—C7A—C8A | 103.52 (10) | O6B—C16B—H16BB | 109.5 |
C6A—C7A—H7AA | 111.1 | C17B—C16B—H16BB | 109.5 |
C8A—C7A—H7AA | 111.1 | H16BA—C16B—H16BB | 108.1 |
C6A—C7A—H7AB | 111.1 | O5A—C15A—O6A | 124.40 (13) |
C8A—C7A—H7AB | 111.1 | O5A—C15A—C8A | 124.96 (13) |
H7AA—C7A—H7AB | 109.0 | O6A—C15A—C8A | 110.63 (11) |
O3B—C12B—O4B | 124.82 (12) | O6A—C16A—C17A | 107.70 (13) |
O3B—C12B—C8B | 125.46 (12) | O6A—C16A—H16AA | 110.2 |
O4B—C12B—C8B | 109.70 (11) | C17A—C16A—H16AA | 110.2 |
C1A—C2A—C3A | 118.70 (13) | O6A—C16A—H16AB | 110.2 |
C1A—C2A—H2A | 120.6 | C17A—C16A—H16AB | 110.2 |
C3A—C2A—H2A | 120.6 | H16AA—C16A—H16AB | 108.5 |
C5B—C6B—C1B | 120.93 (12) | O2A—C10A—H10AA | 109.5 |
C5B—C6B—C7B | 112.25 (11) | O2A—C10A—H10AB | 109.5 |
C1B—C6B—C7B | 126.78 (11) | H10AA—C10A—H10AB | 109.5 |
O2B—C1B—C2B | 124.94 (12) | O2A—C10A—H10AC | 109.5 |
O2B—C1B—C6B | 115.95 (11) | H10AA—C10A—H10AC | 109.5 |
C2B—C1B—C6B | 119.10 (12) | H10AB—C10A—H10AC | 109.5 |
C15A—O6A—C16A | 115.50 (11) | O2B—C10B—H10BA | 109.5 |
C6B—C5B—C4B | 121.29 (12) | O2B—C10B—H10BB | 109.5 |
C6B—C5B—C9B | 111.63 (11) | H10BA—C10B—H10BB | 109.5 |
C4B—C5B—C9B | 127.05 (11) | O2B—C10B—H10BC | 109.5 |
C12A—C8A—C15A | 107.95 (11) | H10BA—C10B—H10BC | 109.5 |
C12A—C8A—C7A | 112.07 (11) | H10BB—C10B—H10BC | 109.5 |
C15A—C8A—C7A | 108.39 (11) | O1B—C11B—H11BA | 109.5 |
C12A—C8A—C9A | 111.49 (11) | O1B—C11B—H11BB | 109.5 |
C15A—C8A—C9A | 110.80 (11) | H11BA—C11B—H11BB | 109.5 |
C7A—C8A—C9A | 106.12 (11) | O1B—C11B—H11BC | 109.5 |
O4B—C13B—C14B | 110.00 (13) | H11BA—C11B—H11BC | 109.5 |
O4B—C13B—H13BA | 109.7 | H11BB—C11B—H11BC | 109.5 |
C14B—C13B—H13BA | 109.7 | C16B—C17B—H17BA | 109.5 |
O4B—C13B—H13BB | 109.7 | C16B—C17B—H17BB | 109.5 |
C14B—C13B—H13BB | 109.7 | H17BA—C17B—H17BB | 109.5 |
H13BA—C13B—H13BB | 108.2 | C16B—C17B—H17BC | 109.5 |
O1B—C4B—C3B | 122.43 (12) | H17BA—C17B—H17BC | 109.5 |
O1B—C4B—C5B | 120.52 (12) | H17BB—C17B—H17BC | 109.5 |
C3B—C4B—C5B | 116.92 (12) | O3A—C13A—C14A | 109.77 (15) |
C1B—C2B—C3B | 118.83 (12) | O3A—C13A—H13AA | 109.7 |
C1B—C2B—H2B | 120.6 | C14A—C13A—H13AA | 109.7 |
C3B—C2B—H2B | 120.6 | O3A—C13A—H13AB | 109.7 |
C6A—C5A—C4A | 121.30 (12) | C14A—C13A—H13AB | 109.7 |
C6A—C5A—C9A | 111.22 (12) | H13AA—C13A—H13AB | 108.2 |
C4A—C5A—C9A | 127.43 (12) | O1A—C11A—H11AA | 109.5 |
C5B—C9B—C8B | 104.20 (10) | O1A—C11A—H11AB | 109.5 |
C5B—C9B—H9BA | 110.9 | H11AA—C11A—H11AB | 109.5 |
C8B—C9B—H9BA | 110.9 | O1A—C11A—H11AC | 109.5 |
C5B—C9B—H9BB | 110.9 | H11AA—C11A—H11AC | 109.5 |
C8B—C9B—H9BB | 110.9 | H11AB—C11A—H11AC | 109.5 |
H9BA—C9B—H9BB | 108.9 | C16A—C17A—H17AA | 109.5 |
C6B—C7B—C8B | 103.88 (10) | C16A—C17A—H17AB | 109.5 |
C6B—C7B—H7BA | 111.0 | H17AA—C17A—H17AB | 109.5 |
C8B—C7B—H7BA | 111.0 | C16A—C17A—H17AC | 109.5 |
C6B—C7B—H7BB | 111.0 | H17AA—C17A—H17AC | 109.5 |
C8B—C7B—H7BB | 111.0 | H17AB—C17A—H17AC | 109.5 |
H7BA—C7B—H7BB | 109.0 | C13B—C14B—H14BA | 109.5 |
O4A—C12A—O3A | 124.68 (14) | C13B—C14B—H14BB | 109.5 |
O4A—C12A—C8A | 125.66 (13) | H14BA—C14B—H14BB | 109.5 |
O3A—C12A—C8A | 109.65 (11) | C13B—C14B—H14BC | 109.5 |
C4B—C3B—C2B | 122.90 (12) | H14BA—C14B—H14BC | 109.5 |
C4B—C3B—Br1B | 118.98 (10) | H14BB—C14B—H14BC | 109.5 |
C2B—C3B—Br1B | 118.12 (10) | C13A—C14A—H14AA | 109.5 |
O1A—C4A—C3A | 122.46 (13) | C13A—C14A—H14AB | 109.5 |
O1A—C4A—C5A | 120.31 (13) | H14AA—C14A—H14AB | 109.5 |
C3A—C4A—C5A | 117.20 (12) | C13A—C14A—H14AC | 109.5 |
C4A—C3A—C2A | 122.79 (13) | H14AA—C14A—H14AC | 109.5 |
C4A—C3A—Br1A | 118.77 (10) | H14AB—C14A—H14AC | 109.5 |
C10A—O2A—C1A—C2A | −3.1 (2) | O1B—C4B—C3B—C2B | −174.67 (12) |
C10A—O2A—C1A—C6A | 175.94 (13) | C5B—C4B—C3B—C2B | 1.2 (2) |
C13B—O4B—C12B—O3B | −2.1 (2) | O1B—C4B—C3B—Br1B | 5.94 (18) |
C13B—O4B—C12B—C8B | 179.38 (11) | C5B—C4B—C3B—Br1B | −178.14 (10) |
C15B—C8B—C12B—O3B | 130.40 (14) | C1B—C2B—C3B—C4B | −0.2 (2) |
C7B—C8B—C12B—O3B | −107.76 (15) | C1B—C2B—C3B—Br1B | 179.16 (10) |
C9B—C8B—C12B—O3B | 10.38 (18) | C11A—O1A—C4A—C3A | 91.78 (18) |
C15B—C8B—C12B—O4B | −51.13 (14) | C11A—O1A—C4A—C5A | −90.35 (17) |
C7B—C8B—C12B—O4B | 70.71 (13) | C6A—C5A—C4A—O1A | −178.95 (13) |
C9B—C8B—C12B—O4B | −171.15 (11) | C9A—C5A—C4A—O1A | 3.8 (2) |
O2A—C1A—C2A—C3A | 178.48 (13) | C6A—C5A—C4A—C3A | −1.0 (2) |
C6A—C1A—C2A—C3A | −0.6 (2) | C9A—C5A—C4A—C3A | −178.18 (13) |
C10B—O2B—C1B—C2B | −2.13 (19) | O1A—C4A—C3A—C2A | 178.74 (13) |
C10B—O2B—C1B—C6B | 178.69 (12) | C5A—C4A—C3A—C2A | 0.8 (2) |
C5B—C6B—C1B—O2B | −179.36 (12) | O1A—C4A—C3A—Br1A | −0.82 (19) |
C7B—C6B—C1B—O2B | 2.87 (19) | C5A—C4A—C3A—Br1A | −178.76 (10) |
C5B—C6B—C1B—C2B | 1.41 (19) | C1A—C2A—C3A—C4A | 0.0 (2) |
C7B—C6B—C1B—C2B | −176.36 (13) | C1A—C2A—C3A—Br1A | 179.52 (10) |
C1B—C6B—C5B—C4B | −0.36 (19) | C16B—O6B—C15B—O5B | 0.3 (2) |
C7B—C6B—C5B—C4B | 177.70 (12) | C16B—O6B—C15B—C8B | −177.28 (11) |
C1B—C6B—C5B—C9B | −178.33 (12) | C12B—C8B—C15B—O5B | 125.31 (15) |
C7B—C6B—C5B—C9B | −0.27 (16) | C7B—C8B—C15B—O5B | 5.15 (19) |
C6A—C7A—C8A—C12A | 139.70 (12) | C9B—C8B—C15B—O5B | −113.18 (15) |
C6A—C7A—C8A—C15A | −101.27 (12) | C12B—C8B—C15B—O6B | −57.16 (13) |
C6A—C7A—C8A—C9A | 17.78 (14) | C7B—C8B—C15B—O6B | −177.32 (10) |
C12B—O4B—C13B—C14B | −93.70 (16) | C9B—C8B—C15B—O6B | 64.35 (13) |
C11B—O1B—C4B—C3B | −89.85 (16) | C4A—C5A—C6A—C1A | 0.4 (2) |
C11B—O1B—C4B—C5B | 94.38 (15) | C9A—C5A—C6A—C1A | 178.00 (12) |
C6B—C5B—C4B—O1B | 175.06 (12) | C4A—C5A—C6A—C7A | −176.81 (13) |
C9B—C5B—C4B—O1B | −7.3 (2) | C9A—C5A—C6A—C7A | 0.83 (16) |
C6B—C5B—C4B—C3B | −0.94 (19) | O2A—C1A—C6A—C5A | −178.72 (12) |
C9B—C5B—C4B—C3B | 176.70 (13) | C2A—C1A—C6A—C5A | 0.4 (2) |
O2B—C1B—C2B—C3B | 179.74 (12) | O2A—C1A—C6A—C7A | −2.0 (2) |
C6B—C1B—C2B—C3B | −1.11 (19) | C2A—C1A—C6A—C7A | 177.13 (13) |
C6B—C5B—C9B—C8B | −5.74 (14) | C8A—C7A—C6A—C5A | −11.90 (15) |
C4B—C5B—C9B—C8B | 176.43 (12) | C8A—C7A—C6A—C1A | 171.15 (13) |
C15B—C8B—C9B—C5B | 130.49 (11) | C6A—C5A—C9A—C8A | 10.63 (15) |
C12B—C8B—C9B—C5B | −110.12 (12) | C4A—C5A—C9A—C8A | −171.92 (13) |
C7B—C8B—C9B—C5B | 9.24 (14) | C12A—C8A—C9A—C5A | −139.68 (11) |
C5B—C6B—C7B—C8B | 6.14 (15) | C15A—C8A—C9A—C5A | 100.07 (12) |
C1B—C6B—C7B—C8B | −175.93 (12) | C7A—C8A—C9A—C5A | −17.39 (14) |
C15B—C8B—C7B—C6B | −128.90 (11) | C15B—O6B—C16B—C17B | −85.52 (15) |
C12B—C8B—C7B—C6B | 111.55 (12) | C16A—O6A—C15A—O5A | 3.2 (2) |
C9B—C8B—C7B—C6B | −9.35 (14) | C16A—O6A—C15A—C8A | −178.16 (12) |
C13A—O3A—C12A—O4A | 5.9 (2) | C12A—C8A—C15A—O5A | −139.96 (14) |
C13A—O3A—C12A—C8A | −174.81 (12) | C7A—C8A—C15A—O5A | 98.44 (16) |
C15A—C8A—C12A—O4A | −118.83 (16) | C9A—C8A—C15A—O5A | −17.62 (19) |
C7A—C8A—C12A—O4A | 0.5 (2) | C12A—C8A—C15A—O6A | 41.38 (14) |
C9A—C8A—C12A—O4A | 119.25 (16) | C7A—C8A—C15A—O6A | −80.21 (13) |
C15A—C8A—C12A—O3A | 61.86 (14) | C9A—C8A—C15A—O6A | 163.72 (11) |
C7A—C8A—C12A—O3A | −178.85 (11) | C15A—O6A—C16A—C17A | 174.49 (13) |
C9A—C8A—C12A—O3A | −60.06 (15) | C12A—O3A—C13A—C14A | 86.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7A—H7AB···O4A | 0.99 | 2.44 | 2.850 (2) | 104 |
C2A—H2A···O5Ai | 0.95 | 2.46 | 3.369 (2) | 160 |
C2B—H2B···O3Bii | 0.95 | 2.56 | 3.419 (2) | 150 |
C13B—H13BB···O3B | 0.99 | 2.36 | 2.717 (2) | 100 |
C9B—H9BA···O3B | 0.99 | 2.40 | 2.852 (2) | 107 |
C7B—H7BA···O5B | 0.99 | 2.38 | 2.849 (2) | 108 |
C9A—H9AB···O5A | 0.99 | 2.46 | 2.840 (2) | 102 |
C16A—H16AA···O3Biii | 0.99 | 2.57 | 3.260 (2) | 127 |
C10A—H10AA···O1Biv | 0.98 | 2.55 | 3.462 (2) | 155 |
C10B—H10BA···O2Av | 0.98 | 2.49 | 3.381 (2) | 150 |
C11B—H11BC···O5Biii | 0.98 | 2.57 | 3.427 (2) | 146 |
C17B—H17BC···O5Aiii | 0.98 | 2.59 | 3.352 (2) | 134 |
C13A—H13AA···Cg1v | 0.99 | 2.82 | 3.799 (2) | 171 |
C16B—H16BB···Cg2iii | 0.99 | 2.57 | 3.459 (2) | 150 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z; (iv) x, y, z+1; (v) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C17H21BrO6 |
Mr | 401.24 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 122 |
a, b, c (Å) | 11.1440 (8), 11.1630 (7), 15.7690 (14) |
α, β, γ (°) | 75.782 (5), 77.534 (7), 73.395 (5) |
V (Å3) | 1799.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.31 |
Crystal size (mm) | 0.59 × 0.34 × 0.19 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | Gaussian integration (Coppens, 1970) |
Tmin, Tmax | 0.427, 0.768 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 72293, 13426, 11251 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.765 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.081, 1.09 |
No. of reflections | 13426 |
No. of parameters | 433 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.60, −0.65 |
Computer programs: COLLECT (Nonius, 1999), DIRAX (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.
C10A—O2A—C1A—C2A | −3.1 (2) | C11B—O1B—C4B—C5B | 94.38 (15) |
C10B—O2B—C1B—C2B | −2.13 (19) | C11A—O1A—C4A—C3A | 91.78 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7A—H7AB···O4A | 0.99 | 2.44 | 2.850 (2) | 104 |
C2A—H2A···O5Ai | 0.95 | 2.46 | 3.369 (2) | 160 |
C2B—H2B···O3Bii | 0.95 | 2.56 | 3.419 (2) | 150 |
C13B—H13BB···O3B | 0.99 | 2.36 | 2.717 (2) | 100 |
C9B—H9BA···O3B | 0.99 | 2.40 | 2.852 (2) | 107 |
C7B—H7BA···O5B | 0.99 | 2.38 | 2.849 (2) | 108 |
C9A—H9AB···O5A | 0.99 | 2.46 | 2.840 (2) | 102 |
C16A—H16AA···O3Biii | 0.99 | 2.57 | 3.260 (2) | 127 |
C10A—H10AA···O1Biv | 0.98 | 2.55 | 3.462 (2) | 155 |
C10B—H10BA···O2Av | 0.98 | 2.49 | 3.381 (2) | 150 |
C11B—H11BC···O5Biii | 0.98 | 2.57 | 3.427 (2) | 146 |
C17B—H17BC···O5Aiii | 0.98 | 2.59 | 3.352 (2) | 134 |
C13A—H13AA···Cg1v | 0.99 | 2.82 | 3.799 (2) | 171 |
C16B—H16BB···Cg2iii | 0.99 | 2.57 | 3.459 (2) | 150 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z; (iv) x, y, z+1; (v) −x, −y+1, −z+1. |
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The title compound, (I), was prepared for use as a building block in the syntheses of single-walled carbon nanotube (SWNT) interacting compounds. It crystallizes in the triclinic space group P1 with two independent molecules in the asymmetric unit (Fig. 1). The corresponding bond lengths and angles of the two molecules agree with each other, but the molecules differ in the orientations of the ester groups. In both molecules, one of the methoxy groups is coplanar with the benzene ring, while the other is almost perpendicular to the benzene ring (see torsions angles in Table 1) and the five-membered rings of the indan ring system adopt envelope conformations. The crystal packing of (I) is stabilized mainly by weak intermolecular C—H···O hydrogen bonds and weak C—H···π(arene) interactions (Table 2 and Fig. 2).