#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/10/4021089.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4021089
loop_
_publ_author_name
'Gary A. Molander'
'Jason P. Burke'
'Patrick J. Carroll'
_publ_section_title
;
 Synthesis and Application of Chiral Cyclopropane-Based Ligands
 in Palladium-Catalyzed Allylic Alkylation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8062
_journal_page_last               8069
_journal_paper_doi               10.1021/jo048782s
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C12 H12 Br I O2'
_chemical_formula_weight         395.03
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                105.979(2)
_cell_angle_beta                 108.666(2)
_cell_angle_gamma                100.361(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8323(11)
_cell_length_b                   9.0392(11)
_cell_length_c                   10.8216(16)
_cell_measurement_temperature    143(1)
_cell_volume                     666.92(16)
_diffrn_ambient_temperature      143(1)
_exptl_crystal_density_diffrn    1.967
_cod_database_code               4021089
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.18047(3) 0.30164(2) 0.784428(19) 0.03712(10) Uani 1 1 d . . .
Br1 Br 0.90208(5) 0.17954(4) 0.01519(3) 0.03616(11) Uani 1 1 d . . .
C1 C 0.2888(4) 0.1196(3) 0.6958(3) 0.0266(6) Uani 1 1 d . . .
H1 H 0.2912 0.0351 0.7364 0.035 Uiso 1 1 calc R . .
C2 C 0.2486(4) 0.0620(3) 0.5434(3) 0.0297(7) Uani 1 1 d . . .
H2A H 0.1788 0.1155 0.4877 0.039 Uiso 1 1 calc R . .
H2B H 0.2235 -0.0523 0.4958 0.039 Uiso 1 1 calc R . .
C3 C 0.4454(4) 0.1560(3) 0.6482(3) 0.0262(6) Uani 1 1 d . . .
H3 H 0.5327 0.0912 0.6627 0.035 Uiso 1 1 calc R . .
C4 C 0.5327(4) 0.3211(3) 0.6569(3) 0.0235(6) Uani 1 1 d . . .
H4 H 0.4361 0.3764 0.6370 0.031 Uiso 1 1 calc R . .
C5 C 0.6926(4) 0.4224(4) 0.7963(3) 0.0332(7) Uani 1 1 d . . .
H5A H 0.7879 0.3686 0.8144 0.050 Uiso 1 1 calc R . .
H5B H 0.6451 0.4375 0.8689 0.050 Uiso 1 1 calc R . .
H5C H 0.7460 0.5253 0.7937 0.050 Uiso 1 1 calc R . .
C6 C 0.5125(4) 0.3048(3) 0.4267(3) 0.0231(6) Uani 1 1 d . . .
C7 C 0.6141(4) 0.2846(3) 0.3321(3) 0.0205(5) Uani 1 1 d . . .
C8 C 0.8086(4) 0.3089(3) 0.3796(3) 0.0237(6) Uani 1 1 d . . .
H8 H 0.8802 0.3440 0.4749 0.032 Uiso 1 1 calc R . .
C9 C 0.8958(4) 0.2814(3) 0.2864(3) 0.0241(6) Uani 1 1 d . . .
H9 H 1.0254 0.2981 0.3182 0.032 Uiso 1 1 calc R . .
C10 C 0.7866(4) 0.2283(3) 0.1447(3) 0.0236(6) Uani 1 1 d . . .
C11 C 0.5950(4) 0.2072(3) 0.0951(3) 0.0274(6) Uani 1 1 d . . .
H11 H 0.5248 0.1744 -0.0003 0.036 Uiso 1 1 calc R . .
C12 C 0.5084(4) 0.2353(3) 0.1888(3) 0.0255(6) Uani 1 1 d . . .
H12 H 0.3792 0.2214 0.1563 0.034 Uiso 1 1 calc R . .
O1 O 0.6179(3) 0.3065(2) 0.55327(18) 0.0240(4) Uani 1 1 d . . .
O2 O 0.3555(3) 0.3180(3) 0.3954(2) 0.0323(5) Uani 1 1 d . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.121(3) . ?
Br1 C10 1.895(3) . ?
C1 C2 1.492(4) . ?
C1 C3 1.494(4) . ?
C2 C3 1.504(4) . ?
C3 C4 1.490(4) . ?
C4 O1 1.465(3) . ?
C4 C5 1.517(4) . ?
C6 O2 1.204(3) . ?
C6 O1 1.348(3) . ?
C6 C7 1.479(4) . ?
C7 C12 1.398(4) . ?
C7 C8 1.396(4) . ?
C8 C9 1.381(4) . ?
C9 C10 1.386(4) . ?
C10 C11 1.379(4) . ?
C11 C12 1.383(4) . ?
