#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:23:41 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178386 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/08/4020800.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_4020800
loop_
_publ_author_name
'Nigel A. Swain'
'Richard C. D. Brown'
'Gordon Bruton'
_publ_section_title
;
 A Versatile Stereoselective Synthesis of endo,exo-Furofuranones:
 Application to the Enantioselective Synthesis of Furofuran Lignans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              122
_journal_page_last               129
_journal_paper_doi               10.1021/jo035365r
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C18 H15 Br O3'
_chemical_formula_weight         359.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 107.376(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3321(2)
_cell_length_b                   13.4800(3)
_cell_length_c                   11.4618(2)
_cell_measurement_temperature    120(2)
_cell_volume                     1523.51(5)
_diffrn_ambient_temperature      120(2)
_exptl_crystal_density_diffrn    1.566
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4020800
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Br1 Br 1.08959(2) -0.088033(15) 1.375677(17) 0.02765(9) Uani 1 1 d . . .
O1 O 0.69205(16) 0.25794(10) 1.01068(13) 0.0302(3) Uani 1 1 d . . .
O2 O 0.66927(15) 0.06642(10) 0.78400(12) 0.0245(3) Uani 1 1 d . . .
O3 O 0.62696(15) -0.04745(10) 0.90750(13) 0.0275(3) Uani 1 1 d . . .
C1 C 0.6334(2) 0.16960(15) 1.04211(18) 0.0252(4) Uani 1 1 d . . .
C2 C 0.5501(2) 0.12296(15) 0.91664(17) 0.0225(4) Uani 1 1 d . . .
C3 C 0.5453(2) 0.20650(15) 0.82348(18) 0.0240(4) Uani 1 1 d . . .
C4 C 0.5947(3) 0.29705(17) 0.9037(2) 0.0308(5) Uani 1 1 d . . .
C5 C 0.61815(19) 0.03761(15) 0.87361(16) 0.0219(4) Uani 1 1 d . . .
C6 C 0.6474(2) 0.17242(14) 0.75755(18) 0.0225(4) Uani 1 1 d . . .
C7 C 0.7452(2) 0.10601(14) 1.12243(17) 0.0232(4) Uani 1 1 d . . .
C8 C 0.8687(2) 0.09599(15) 1.09818(18) 0.0244(4) Uani 1 1 d . . .
C9 C 0.9710(2) 0.03685(15) 1.17187(18) 0.0238(4) Uani 1 1 d . . .
C10 C 0.9471(2) -0.01237(14) 1.27009(17) 0.0218(4) Uani 1 1 d . . .
C11 C 0.8245(2) -0.00438(15) 1.29511(18) 0.0240(4) Uani 1 1 d . . .
C12 C 0.7240(2) 0.05550(16) 1.22103(18) 0.0248(4) Uani 1 1 d . . .
C13 C 0.6026(2) 0.18782(14) 0.62114(17) 0.0238(4) Uani 1 1 d . . .
C14 C 0.6618(2) 0.26224(16) 0.5710(2) 0.0291(5) Uani 1 1 d . . .
C15 C 0.6229(3) 0.27786(19) 0.4460(2) 0.0401(6) Uani 1 1 d . . .
C16 C 0.5235(3) 0.2177(2) 0.3699(2) 0.0441(7) Uani 1 1 d . . .
C17 C 0.4633(3) 0.14362(19) 0.4193(2) 0.0388(6) Uani 1 1 d . . .
C18 C 0.5023(2) 0.12882(17) 0.54493(19) 0.0304(5) Uani 1 1 d . . .
H1 H 0.566(2) 0.1879(16) 1.083(2) 0.026(6) Uiso 1 1 d . . .
H2 H 0.465(2) 0.1012(15) 0.9249(19) 0.019(5) Uiso 1 1 d . . .
H3 H 0.457(2) 0.2135(17) 0.768(2) 0.027(6) Uiso 1 1 d . . .
H4A H 0.521(3) 0.3290(18) 0.923(2) 0.031(6) Uiso 1 1 d . . .
H4B H 0.647(3) 0.3451(18) 0.867(2) 0.034(6) Uiso 1 1 d . . .
H6 H 0.736(2) 0.2047(15) 0.7954(19) 0.018(5) Uiso 1 1 d . . .
H8 H 0.884(2) 0.1333(17) 1.031(2) 0.030(6) Uiso 1 1 d . . .
H9 H 1.055(2) 0.0295(16) 1.1581(19) 0.021(5) Uiso 1 1 d . . .
H11 H 0.814(3) -0.0411(19) 1.361(2) 0.037(7) Uiso 1 1 d . . .
H12 H 0.640(3) 0.0630(17) 1.239(2) 0.031(6) Uiso 1 1 d . . .
H14 H 0.734(3) 0.3018(18) 0.624(2) 0.035(7) Uiso 1 1 d . . .
H15 H 0.668(3) 0.327(2) 0.414(2) 0.046(8) Uiso 1 1 d . . .
H16 H 0.497(3) 0.228(2) 0.283(3) 0.066(9) Uiso 1 1 d . . .
H17 H 0.396(3) 0.101(2) 0.371(2) 0.042(7) Uiso 1 1 d . . .
H18 H 0.461(3) 0.0769(18) 0.579(2) 0.035(7) Uiso 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
Br1 C10 1.8993(19) . ?
O1 C1 1.430(2) . ?
O1 C4 1.434(3) . ?
O2 C5 1.345(2) . ?
O2 C6 1.464(2) . ?
O3 C5 1.205(2) . ?
C1 C7 1.510(3) . ?
C1 C2 1.570(3) . ?
C1 H1 0.98(2) . ?
C2 C5 1.506(3) . ?
C2 C3 1.543(3) . ?
C2 H2 0.96(2) . ?
C3 C4 1.522(3) . ?
C3 C6 1.540(3) . ?
C3 H3 0.95(2) . ?
C4 H4A 0.95(3) . ?
C4 H4B 1.01(3) . ?
C6 C13 1.507(3) . ?
C6 H6 0.99(2) . ?
C7 C12 1.391(3) . ?
C7 C8 1.392(3) . ?
C8 C9 1.390(3) . ?
C8 H8 0.98(2) . ?
C9 C10 1.391(3) . ?
C9 H9 0.93(2) . ?
C10 C11 1.385(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.94(3) . ?
C12 H12 0.96(3) . ?
C13 C14 1.386(3) . ?
C13 C18 1.389(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.97(3) . ?
C15 C16 1.392(4) . ?
C15 H15 0.95(3) . ?
C16 C17 1.384(4) . ?
C16 H16 0.96(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.94(3) . ?
C18 H18 0.96(3) . ?
