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#$Date: 2016-03-22 11:13:47 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178890 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/19/4111945.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_4111945
loop_
_publ_author_name
'Siu Hong Yu'
'Michael J. Ferguson'
'Robert McDonald'
'Dennis G. Hall'
_publ_contact_author_address
; Department of Chemistry
  University of Alberta
  Edmonton, Alberta T6G 2G2
  Canada
;
_publ_contact_author_email       dennis.hall@ualberta.ca
_publ_contact_author_fax         1(780)4928231
_publ_contact_author_name        'Dr. Dennis G. Hall'
_publ_contact_author_phone       1(780)4923141
_publ_section_title
;
 Brønsted Acid-Catalyzed Allylboration: Short and Stereodivergent
 Synthesis of All Four Eupomatilone Diastereomers with Crystallographic
 Assignments
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12808
_journal_page_last               12809
_journal_paper_doi               10.1021/ja054171l
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C15 H19 Br O5'
_chemical_formula_sum            'C15 H19 Br O5'
_chemical_formula_weight         359.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual editing of SHELXL template'
_cell_angle_alpha                90.00
_cell_angle_beta                 105.3820(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2249(6)
_cell_length_b                   9.8448(6)
_cell_length_c                   15.8781(10)
_cell_measurement_reflns_used    4455
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.66
_cell_volume                     1541.07(16)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11618
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.686
_exptl_absorpt_correction_T_max  0.6024
_exptl_absorpt_correction_T_min  0.3197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0336P)²+0.8303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0685
_reflns_number_gt                2830
_reflns_number_total             3154
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja054171lsi20050624_122957.cif
_cod_data_source_block           14
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4111945
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br Br 0.42004(2) 0.17530(2) 0.665301(14) 0.03750(8) Uani 1 1 d .
O1 O 0.04610(12) 0.12166(13) 0.43801(9) 0.0285(3) Uani 1 1 d .
O2 O -0.06929(14) -0.01044(15) 0.33013(9) 0.0378(3) Uani 1 1 d .
O3 O 0.47498(13) 0.47724(14) 0.67381(8) 0.0312(3) Uani 1 1 d .
O4 O 0.34498(14) 0.67948(12) 0.56128(9) 0.0326(3) Uani 1 1 d .
O5 O 0.12099(14) 0.62338(13) 0.43479(9) 0.0316(3) Uani 1 1 d .
C1 C 0.03617(18) 0.01621(18) 0.38147(12) 0.0272(4) Uani 1 1 d .
C2 C 0.17099(19) -0.05507(18) 0.39701(12) 0.0278(4) Uani 1 1 d .
H2 H 0.1713 -0.1311 0.4388 0.033 Uiso 1 1 calc R
C3 C 0.27265(18) 0.05276(18) 0.44579(13) 0.0295(4) Uani 1 1 d .
H3 H 0.3493 0.0070 0.4888 0.035 Uiso 1 1 calc R
C4 C 0.18313(17) 0.12950(18) 0.49523(12) 0.0264(4) Uani 1 1 d .
H4 H 0.1861 0.0798 0.5506 0.032 Uiso 1 1 calc R
C5 C 0.1949(2) -0.1166(2) 0.31479(14) 0.0380(5) Uani 1 1 d .
H5A H 0.1227 -0.1820 0.2899 0.046 Uiso 1 1 calc R
H5B H 0.2828 -0.1632 0.3292 0.046 Uiso 1 1 calc R
H5C H 0.1948 -0.0445 0.2722 0.046 Uiso 1 1 calc R
C6 C 0.3288(2) 0.1435(2) 0.38581(17) 0.0438(5) Uani 1 1 d .
H6A H 0.3912 0.2102 0.4209 0.053 Uiso 1 1 calc R
H6B H 0.2538 0.1909 0.3451 0.053 Uiso 1 1 calc R
H6C H 0.3774 0.0877 0.3529 0.053 Uiso 1 1 calc R
C11 C 0.21891(17) 0.27644(18) 0.51652(12) 0.0246(4) Uani 1 1 d .
C12 C 0.32614(18) 0.31057(18) 0.58744(12) 0.0260(4) Uani 1 1 d .
C13 C 0.36790(18) 0.44526(18) 0.60415(11) 0.0255(4) Uani 1 1 d .
C14 C 0.29875(18) 0.54820(17) 0.55036(12) 0.0250(4) Uani 1 1 d .
C15 C 0.18592(18) 0.51546(18) 0.48128(12) 0.0253(4) Uani 1 1 d .
C16 C 0.14856(18) 0.38077(18) 0.46393(11) 0.0247(4) Uani 1 1 d .
H16 H 0.0741 0.3592 0.4156 0.030 Uiso 1 1 calc R
C17 C 0.60202(19) 0.4795(2) 0.65055(14) 0.0364(4) Uani 1 1 d .
H17A H 0.6756 0.5022 0.7022 0.044 Uiso 1 1 calc R
H17B H 0.5978 0.5479 0.6051 0.044 Uiso 1 1 calc R
H17C H 0.6190 0.3900 0.6286 0.044 Uiso 1 1 calc R
C18 C 0.2944(2) 0.7570(2) 0.62181(13) 0.0349(4) Uani 1 1 d .
H18A H 0.3320 0.8491 0.6259 0.042 Uiso 1 1 calc R
H18B H 0.3213 0.7136 0.6794 0.042 Uiso 1 1 calc R
H18C H 0.1953 0.7615 0.6017 0.042 Uiso 1 1 calc R
C19 C 0.0062(2) 0.5949(2) 0.36286(13) 0.0333(4) Uani 1 1 d .
H19A H -0.0302 0.6802 0.3342 0.040 Uiso 1 1 calc R
H19B H -0.0638 0.5490 0.3842 0.040 Uiso 1 1 calc R
H19C H 0.0341 0.5361 0.3209 0.040 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C4 110.10(14)
C13 O3 C17 112.21(14)
C14 O4 C18 114.52(14)
C15 O5 C19 117.29(14)
O2 C1 O1 120.93(17)
O2 C1 C2 129.01(17)
O1 C1 C2 110.04(15)
C1 C2 C5 113.23(16)
C1 C2 C3 103.11(14)
C5 C2 C3 117.77(16)
C6 C3 C2 113.87(17)
C6 C3 C4 113.65(15)
C2 C3 C4 100.36(14)
O1 C4 C11 109.07(14)
O1 C4 C3 104.94(14)
C11 C4 C3 116.10(14)
C12 C11 C16 118.52(16)
C12 C11 C4 120.41(16)
C16 C11 C4 121.03(16)
C11 C12 C13 121.31(16)
C11 C12 Br 120.88(13)
C13 C12 Br 117.81(14)
O3 C13 C14 119.68(16)
O3 C13 C12 120.65(16)
C14 C13 C12 119.66(16)
O4 C14 C13 120.45(16)
O4 C14 C15 120.01(16)
C13 C14 C15 119.43(16)
O5 C15 C16 124.69(17)
O5 C15 C14 115.23(15)
C16 C15 C14 120.08(16)
C15 C16 C11 120.87(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C12 1.8958(18)
O1 C1 1.359(2)
O1 C4 1.456(2)
O2 C1 1.196(2)
O3 C13 1.371(2)
O3 C17 1.442(2)
O4 C14 1.371(2)
O4 C18 1.427(2)
O5 C15 1.362(2)
O5 C19 1.431(2)
C1 C2 1.508(3)
C2 C5 1.517(3)
C2 C3 1.543(3)
C3 C6 1.525(3)
C3 C4 1.551(3)
C4 C11 1.508(2)
C11 C12 1.389(3)
C11 C16 1.397(3)
C12 C13 1.397(2)
C13 C14 1.391(3)
C14 C15 1.402(3)
C15 C16 1.387(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 O1 C1 O2 178.00(17)
C4 O1 C1 C2 -0.63(19)
O2 C1 C2 C5 32.8(3)
O1 C1 C2 C5 -148.74(16)
O2 C1 C2 C3 161.13(19)
O1 C1 C2 C3 -20.38(19)
C1 C2 C3 C6 -90.80(18)
C5 C2 C3 C6 34.7(2)
C1 C2 C3 C4 30.98(17)
C5 C2 C3 C4 156.46(17)
C1 O1 C4 C11 146.46(14)
C1 O1 C4 C3 21.44(18)
C6 C3 C4 O1 89.81(19)
C2 C3 C4 O1 -32.13(17)
C6 C3 C4 C11 -30.7(2)
C2 C3 C4 C11 -152.61(16)
O1 C4 C11 C12 162.13(15)
C3 C4 C11 C12 -79.6(2)
O1 C4 C11 C16 -20.1(2)
C3 C4 C11 C16 98.1(2)
C16 C11 C12 C13 -3.0(3)
C4 C11 C12 C13 174.77(16)
C16 C11 C12 Br 176.59(13)
C4 C11 C12 Br -5.6(2)
C17 O3 C13 C14 -89.3(2)
C17 O3 C13 C12 91.7(2)
C11 C12 C13 O3 -179.20(15)
Br C12 C13 O3 1.2(2)
C11 C12 C13 C14 1.8(3)
Br C12 C13 C14 -177.80(13)
C18 O4 C14 C13 -88.7(2)
C18 O4 C14 C15 95.3(2)
O3 C13 C14 O4 6.4(2)
C12 C13 C14 O4 -174.57(15)
O3 C13 C14 C15 -177.46(15)
C12 C13 C14 C15 1.5(3)
C19 O5 C15 C16 -0.1(2)
C19 O5 C15 C14 179.19(15)
O4 C14 C15 O5 -6.8(2)
C13 C14 C15 O5 177.03(15)
O4 C14 C15 C16 172.50(15)
C13 C14 C15 C16 -3.6(3)
O5 C15 C16 C11 -178.30(16)
C14 C15 C16 C11 2.4(3)
C12 C11 C16 C15 0.9(3)
C4 C11 C16 C15 -176.89(16)
