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The title compound, C18H25BrO, is a chiral bicyclo­[2.2.1]heptane derivative with the benz­yloxy group oriented endo with respect to the ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031606/ez2019sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031606/ez2019Isup2.hkl
Contains datablock I

CCDC reference: 620960

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.038
  • wR factor = 0.096
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C7
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: 0.459 0.525 RT(exp) = 1.146 PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.16 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.72 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT410_ALERT_2_C Short Intra H...H Contact H12B .. H18B .. 1.91 Ang.
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 27.51 From the CIF: _reflns_number_total 3480 Count of symmetry unique reflns 2040 Completeness (_total/calc) 170.59% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1440 Fraction of Friedel pairs measured 0.706 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(2S,7R)-2-Benzyloxy-7-bromomethyl-1,2,7-trimethylbicyclo[2.2.1]heptane top
Crystal data top
C18H25BrOF(000) = 352
Mr = 337.29Dx = 1.352 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.1721 (3) ÅCell parameters from 1962 reflections
b = 7.9624 (3) Åθ = 2.6–23.6°
c = 14.5849 (6) ŵ = 2.48 mm1
β = 95.719 (2)°T = 294 K
V = 828.76 (6) Å3Block, colorless
Z = 20.43 × 0.27 × 0.26 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer
2336 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 27.5°, θmin = 2.8°
φ and ω scansh = 79
5095 measured reflectionsk = 1010
3480 independent reflectionsl = 1818
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.0411P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096(Δ/σ)max < 0.001
S = 0.97Δρmax = 0.32 e Å3
3480 reflectionsΔρmin = 0.37 e Å3
185 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
7 restraintsExtinction coefficient: 0.060 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.030 (12)
Special details top

Experimental. [α]D20 -33 (c 1.7, CHCl3); IR (film): 3006, 2956, 2874, 1605, 1455, 1384, 1312, 1250, 1120, 1081, 734, 696 cm-1; 1H NMR (300 MHz, CDCl3): δ 7.33 (d, 4H, J = 4.2 Hz), 7.28–7.24 (m, 1H), 4.45 (d, 2H, J = 3.0 Hz), 3.78 (d, 1H, J = 9.9 Hz), 3.21 (d, 1H, J = 9.9 Hz), 2.62–2.55 (m, 1H), 2.03 (t, 1H, J = 4.5 Hz), 1.82–1.74 (m, 2H), 1.65–1.53 (m, 1H), 1.40 (s, 3H), 1.40–1.22 (m, 2H), 1.16 (s, 3H), 0.93 (s, 3H); 13C NMR (75 MHz, CDCl3): δ 140.1, 128.2 (2 C), 127.0, 126.7 (2 C), 83.6, 64.8, 54.5, 53.5, 43.3, 42.8, 41.1, 28.8, 26.4, 23.9, 17.5, 12.3.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.33807 (6)0.24169 (6)1.08282 (2)0.0830 (2)
C10.2296 (6)0.2012 (6)0.4937 (3)0.0780 (14)
C20.1800 (6)0.2745 (8)0.4120 (2)0.0780 (16)
H20.06090.32080.40090.094*
C30.2991 (8)0.2832 (7)0.3447 (3)0.0879 (17)
H30.26080.33600.28910.106*
C40.4716 (8)0.2156 (9)0.3585 (3)0.0983 (17)
H40.55450.22410.31360.118*
C60.4004 (10)0.1289 (8)0.5077 (4)0.1098 (18)
H60.43640.07520.56330.132*
C70.0995 (8)0.1880 (9)0.5670 (3)0.128 (3)
H7A0.02250.23190.54410.153*
H7B0.08440.07100.58320.153*
C180.2898 (6)0.3760 (5)0.9689 (2)0.0603 (9)
H18A0.22890.48020.98320.072*
H18B0.40840.40410.94610.072*
C50.5228 (9)0.1344 (8)0.4393 (5)0.120 (2)
H50.63940.08270.44890.144*
C80.0788 (5)0.2510 (9)0.7278 (2)0.0699 (10)
C150.0299 (5)0.2747 (6)0.9255 (3)0.0707 (12)
H15A0.02260.22810.98640.106*
H15B0.10790.20470.88400.106*
H15C0.08250.38550.92600.106*
C140.1671 (4)0.2839 (4)0.8935 (2)0.0487 (9)
C130.1869 (5)0.3763 (5)0.7982 (3)0.0475 (8)
C120.3983 (5)0.3471 (5)0.7893 (3)0.0530 (9)
H12A0.42370.34950.72520.064*
H12B0.47420.43200.82300.064*
C100.2460 (5)0.1195 (4)0.8614 (3)0.0561 (9)
H100.25210.02960.90740.067*
C90.1186 (7)0.0822 (7)0.7745 (3)0.0775 (14)
H9A0.00320.03040.78960.093*
H9B0.17980.00710.73460.093*
C170.1310 (5)0.2947 (8)0.7052 (3)0.097 (2)
H17A0.14290.38950.66440.146*
H17B0.18470.32160.76120.146*
H17C0.19560.20020.67620.146*
C110.4384 (5)0.1720 (5)0.8314 (3)0.0597 (10)
H11A0.53280.17740.88370.072*
H11B0.47960.09460.78610.072*
C160.1283 (6)0.5578 (5)0.7904 (3)0.0730 (12)
H16A0.14660.59880.73010.110*
H16B0.20250.62270.83590.110*
H16C0.00170.56740.80020.110*
O10.1688 (4)0.2767 (5)0.64360 (16)0.0847 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1108 (4)0.0852 (3)0.0521 (2)0.0089 (3)0.00362 (19)0.0109 (3)
C10.080 (3)0.097 (4)0.055 (2)0.025 (3)0.005 (2)0.001 (2)
C20.086 (3)0.084 (5)0.062 (2)0.007 (2)0.005 (2)0.014 (2)
C30.118 (4)0.100 (5)0.0464 (18)0.014 (3)0.007 (2)0.003 (2)
C40.105 (4)0.117 (5)0.075 (3)0.015 (4)0.019 (3)0.038 (4)
C60.133 (5)0.110 (4)0.079 (3)0.003 (4)0.027 (4)0.030 (3)
C70.112 (3)0.196 (7)0.074 (3)0.081 (4)0.005 (3)0.015 (3)
C180.083 (3)0.053 (2)0.0474 (17)0.0022 (19)0.0206 (18)0.0045 (15)
C50.100 (4)0.121 (4)0.132 (5)0.043 (4)0.017 (4)0.020 (4)
C80.0567 (19)0.093 (3)0.0581 (17)0.014 (3)0.0028 (15)0.014 (3)
C150.057 (2)0.084 (3)0.075 (2)0.000 (2)0.0306 (18)0.020 (2)
C140.0442 (17)0.051 (3)0.0526 (16)0.0011 (14)0.0128 (15)0.0092 (13)
C130.0381 (18)0.055 (2)0.052 (2)0.0026 (16)0.0143 (17)0.0082 (16)
C120.0419 (19)0.067 (2)0.052 (2)0.0018 (17)0.0123 (17)0.0003 (17)
C100.060 (2)0.047 (2)0.061 (2)0.0096 (17)0.0063 (19)0.0069 (17)
C90.065 (3)0.093 (4)0.074 (3)0.024 (2)0.007 (2)0.007 (3)
C170.048 (2)0.157 (6)0.086 (3)0.012 (2)0.003 (2)0.027 (3)
C110.047 (2)0.069 (2)0.065 (2)0.0114 (17)0.0132 (19)0.0034 (18)
C160.072 (3)0.066 (3)0.085 (3)0.023 (2)0.030 (2)0.025 (2)
O10.0752 (16)0.130 (3)0.0482 (12)0.036 (2)0.0044 (12)0.0023 (16)
Geometric parameters (Å, º) top
Br1—C181.978 (3)C15—H15A0.9600
C1—C21.342 (6)C15—H15B0.9600
C1—C61.350 (7)C15—H15C0.9600
C1—C71.491 (6)C14—C101.519 (5)
C2—C31.366 (6)C14—C131.591 (5)
C2—H20.9300C13—C161.506 (6)
C3—C41.346 (7)C13—C121.552 (5)
C3—H30.9300C12—C111.539 (5)
C4—C51.362 (8)C12—H12A0.9700
C4—H40.9300C12—H12B0.9700
C6—C51.394 (8)C10—C91.515 (6)
C6—H60.9300C10—C111.546 (5)
C7—O11.373 (6)C10—H100.9800
C7—H7A0.9700C9—H9A0.9700
C7—H7B0.9700C9—H9B0.9700
C18—C141.526 (5)C17—H17A0.9600
C18—H18A0.9700C17—H17B0.9600
C18—H18B0.9700C17—H17C0.9600
C5—H50.9300C11—H11A0.9700
C8—O11.457 (4)C11—H11B0.9700
C8—C91.521 (8)C16—H16A0.9600
C8—C171.547 (6)C16—H16B0.9600
C8—C131.579 (6)C16—H16C0.9600
C15—C141.533 (4)
C2—C1—C6118.4 (4)C18—C14—C13108.2 (3)
C2—C1—C7122.5 (5)C15—C14—C13116.9 (3)
C6—C1—C7119.0 (5)C16—C13—C12113.9 (3)
C1—C2—C3122.1 (5)C16—C13—C8116.2 (4)
C1—C2—H2119.0C12—C13—C8105.7 (3)
C3—C2—H2119.0C16—C13—C14117.5 (3)
C4—C3—C2120.2 (5)C12—C13—C14100.2 (3)
C4—C3—H3119.9C8—C13—C14101.3 (3)
C2—C3—H3119.9C11—C12—C13104.3 (3)
C3—C4—C5119.0 (5)C11—C12—H12A110.9
C3—C4—H4120.5C13—C12—H12A110.9
C5—C4—H4120.5C11—C12—H12B110.9
C1—C6—C5120.3 (5)C13—C12—H12B110.9
C1—C6—H6119.8H12A—C12—H12B108.9
C5—C6—H6119.8C9—C10—C14102.4 (3)
O1—C7—C1110.2 (4)C9—C10—C11107.3 (3)
O1—C7—H7A109.6C14—C10—C11103.0 (3)
C1—C7—H7A109.6C9—C10—H10114.3
O1—C7—H7B109.6C14—C10—H10114.3
C1—C7—H7B109.6C11—C10—H10114.3
H7A—C7—H7B108.1C10—C9—C8105.8 (4)
C14—C18—Br1112.7 (2)C10—C9—H9A110.6
C14—C18—H18A109.1C8—C9—H9A110.6
Br1—C18—H18A109.1C10—C9—H9B110.6
C14—C18—H18B109.1C8—C9—H9B110.6
Br1—C18—H18B109.1H9A—C9—H9B108.7
H18A—C18—H18B107.8C8—C17—H17A109.5
C4—C5—C6119.9 (5)C8—C17—H17B109.5
C4—C5—H5120.0H17A—C17—H17B109.5
C6—C5—H5120.0C8—C17—H17C109.5
O1—C8—C9115.0 (5)H17A—C17—H17C109.5
O1—C8—C17107.0 (3)H17B—C17—H17C109.5
C9—C8—C17115.4 (4)C12—C11—C10102.8 (3)
O1—C8—C13103.3 (3)C12—C11—H11A111.2
C9—C8—C13102.0 (3)C10—C11—H11A111.2
C17—C8—C13113.6 (5)C12—C11—H11B111.2
C14—C15—H15A109.5C10—C11—H11B111.2
C14—C15—H15B109.5H11A—C11—H11B109.1
H15A—C15—H15B109.5C13—C16—H16A109.5
C14—C15—H15C109.5C13—C16—H16B109.5
H15A—C15—H15C109.5H16A—C16—H16B109.5
H15B—C15—H15C109.5C13—C16—H16C109.5
C10—C14—C18115.5 (3)H16A—C16—H16C109.5
C10—C14—C15115.8 (3)H16B—C16—H16C109.5
C18—C14—C15106.6 (3)C7—O1—C8117.3 (3)
C10—C14—C1393.5 (3)
C6—C1—C2—C32.4 (8)C18—C14—C13—C1263.3 (3)
C7—C1—C2—C3178.8 (5)C15—C14—C13—C12176.4 (3)
C1—C2—C3—C40.7 (9)C10—C14—C13—C853.4 (3)
C2—C3—C4—C52.0 (9)C18—C14—C13—C8171.7 (3)
C2—C1—C6—C51.5 (9)C15—C14—C13—C867.9 (4)
C7—C1—C6—C5177.9 (5)C16—C13—C12—C11161.3 (3)
C2—C1—C7—O1116.7 (6)C8—C13—C12—C1169.9 (4)
C6—C1—C7—O167.0 (8)C14—C13—C12—C1135.0 (3)
C3—C4—C5—C62.9 (10)C18—C14—C10—C9167.5 (3)
C1—C6—C5—C41.2 (10)C15—C14—C10—C966.8 (4)
Br1—C18—C14—C1060.3 (3)C13—C14—C10—C955.4 (3)
Br1—C18—C14—C1570.0 (3)C18—C14—C10—C1156.2 (4)
Br1—C18—C14—C13163.4 (2)C15—C14—C10—C11178.1 (3)
O1—C8—C13—C1679.7 (4)C13—C14—C10—C1155.9 (3)
C9—C8—C13—C16160.7 (3)C14—C10—C9—C838.0 (4)
C17—C8—C13—C1635.8 (4)C11—C10—C9—C870.0 (4)
O1—C8—C13—C1247.7 (4)O1—C8—C9—C10108.8 (4)
C9—C8—C13—C1271.9 (3)C17—C8—C9—C10125.9 (4)
C17—C8—C13—C12163.2 (3)C13—C8—C9—C102.2 (4)
O1—C8—C13—C14151.8 (3)C13—C12—C11—C100.7 (3)
C9—C8—C13—C1432.2 (3)C9—C10—C11—C1271.6 (4)
C17—C8—C13—C1492.7 (4)C14—C10—C11—C1236.1 (3)
C10—C14—C13—C16178.9 (3)C1—C7—O1—C8168.4 (5)
C18—C14—C13—C1660.6 (4)C9—C8—O1—C772.2 (5)
C15—C14—C13—C1659.7 (5)C17—C8—O1—C757.5 (7)
C10—C14—C13—C1255.0 (3)C13—C8—O1—C7177.6 (5)
 

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