#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:31:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178815 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/69/4106932.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_4106932
loop_
_publ_author_name
'Scott A. Snyder'
'Daniel S. Treitler'
'Alexandria P. Brucks'
'Wesley Sattler'
_publ_section_title
;
 A General Strategy for the Stereocontrolled Preparation of Diverse 8- and
 9-Membered Laurencia-Type Bromoethers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15898
_journal_page_last               15901
_journal_paper_doi               10.1021/ja2069449
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C25 H27 Br3 O5'
_chemical_formula_weight         647.20
_chemical_name_systematic
; 
 ? 
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.375(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5031(15)
_cell_length_b                   10.0832(10)
_cell_length_c                   17.4974(18)
_cell_measurement_reflns_used    7028
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.35
_cell_volume                     2499.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.1129
_diffrn_reflns_av_sigmaI/netI    0.0982
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39558
_diffrn_reflns_theta_full        30.64
_diffrn_reflns_theta_max         30.64
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    4.876
_exptl_absorpt_correction_T_max  0.9088
_exptl_absorpt_correction_T_min  0.3321
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         7700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0253P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                4045
_reflns_number_total             7700
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2069449_si_005.cif
_cod_data_source_block           dw8fs10
_cod_database_code               4106932
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
Br1 Br -0.11471(3) 0.12932(4) 0.45341(2) 0.03992(12) Uani 1 1 d .
Br2 Br -0.14805(3) 0.82108(4) 0.08838(2) 0.04031(12) Uani 1 1 d .
Br3 Br 0.63966(3) 0.00366(4) 0.18648(2) 0.03756(11) Uani 1 1 d .
O1 O 0.17675(16) 0.1218(2) 0.20053(13) 0.0241(5) Uani 1 1 d .
O2 O 0.18655(16) 0.3439(2) 0.12431(13) 0.0256(5) Uani 1 1 d .
O3 O 0.04042(17) 0.1161(2) 0.11037(14) 0.0366(6) Uani 1 1 d .
O4 O 0.25672(16) 0.4930(2) 0.06085(14) 0.0299(6) Uani 1 1 d .
O5 O 0.43456(15) 0.1229(2) 0.11700(12) 0.0226(5) Uani 1 1 d .
C1 C 0.3479(3) -0.0384(3) 0.0371(2) 0.0330(9) Uani 1 1 d .
H1A H 0.4012 -0.0532 0.0119 0.050 Uiso 1 1 calc R
H1B H 0.3077 0.0323 0.0095 0.050 Uiso 1 1 calc R
H1C H 0.3111 -0.1203 0.0352 0.050 Uiso 1 1 calc R
C2 C 0.7152(2) 0.2821(4) 0.1214(2) 0.0382(10) Uani 1 1 d .
H2A H 0.7221 0.3390 0.0775 0.057 Uiso 1 1 calc R
H2B H 0.7434 0.1952 0.1160 0.057 Uiso 1 1 calc R
H2C H 0.7473 0.3231 0.1707 0.057 Uiso 1 1 calc R
C3 C -0.1064(3) 0.1288(3) 0.2932(2) 0.0315(9) Uani 1 1 d .
H3A H -0.1732 0.1225 0.2841 0.038 Uiso 1 1 calc R
C4 C -0.0616(2) 0.1281(3) 0.2317(2) 0.0302(8) Uani 1 1 d .
H4A H -0.0976 0.1205 0.1797 0.036 Uiso 1 1 calc R
C5 C 0.4443(2) 0.3091(3) 0.2028(2) 0.0258(8) Uani 1 1 d .
H5A H 0.4497 0.3679 0.1587 0.031 Uiso 1 1 calc R
H5B H 0.4828 0.3483 0.2511 0.031 Uiso 1 1 calc R
C6 C -0.0510(2) 0.5765(3) 0.1071(2) 0.0290(8) Uani 1 1 d .
H6A H -0.1066 0.5435 0.1209 0.035 Uiso 1 1 calc R
C7 C 0.0434(2) 0.1502(3) 0.3828(2) 0.0255(8) Uani 1 1 d .
H7A H 0.0791 0.1577 0.4349 0.031 Uiso 1 1 calc R
C8 C 0.3845(2) 0.0016(3) 0.12130(19) 0.0240(8) Uani 1 1 d .
H8A H 0.4308 -0.0669 0.1470 0.029 Uiso 1 1 calc R
C9 C 0.0332(3) 0.7568(4) 0.0637(2) 0.0301(9) Uani 1 1 d .
H9A H 0.0355 0.8471 0.0486 0.036 Uiso 1 1 calc R
C10 C 0.1060(2) 0.5425(3) 0.08674(19) 0.0219(7) Uani 1 1 d .
C11 C 0.1085(2) 0.6729(3) 0.0636(2) 0.0285(8) Uani 1 1 d .
H11A H 0.1627 0.7054 0.0473 0.034 Uiso 1 1 calc R
C12 C 0.2709(2) 0.2603(3) 0.13674(19) 0.0230(8) Uani 1 1 d .
H12A H 0.3008 0.2673 0.0904 0.028 Uiso 1 1 calc R
C13 C 0.4853(2) 0.1748(3) 0.18973(19) 0.0240(8) Uani 1 1 d .
H13A H 0.4778 0.1135 0.2329 0.029 Uiso 1 1 calc R
C14 C -0.0532(2) 0.1389(3) 0.3686(2) 0.0259(8) Uani 1 1 d .
C15 C 0.6110(2) 0.2649(3) 0.1212(2) 0.0267(8) Uani 1 1 d .
H15A H 0.5824 0.3539 0.1218 0.032 Uiso 1 1 calc R
H15B H 0.5801 0.2211 0.0717 0.032 Uiso 1 1 calc R
C16 C -0.0451(2) 0.7068(3) 0.0861(2) 0.0283(8) Uani 1 1 d .
C17 C 0.0877(2) 0.1506(3) 0.3211(2) 0.0242(8) Uani 1 1 d .
H17A H 0.1544 0.1595 0.3307 0.029 Uiso 1 1 calc R
C18 C 0.1911(2) 0.4589(3) 0.08810(19) 0.0227(8) Uani 1 1 d .
C19 C 0.0257(2) 0.4939(3) 0.10780(19) 0.0277(8) Uani 1 1 d .
H19A H 0.0230 0.4036 0.1228 0.033 Uiso 1 1 calc R
C20 C 0.0364(2) 0.1383(3) 0.2448(2) 0.0232(8) Uani 1 1 d .
C21 C 0.3079(2) 0.0149(3) 0.1682(2) 0.0255(8) Uani 1 1 d .
H21A H 0.3388 0.0338 0.2232 0.031 Uiso 1 1 calc R
H21B H 0.2758 -0.0719 0.1674 0.031 Uiso 1 1 calc R
C22 C 0.5897(2) 0.1860(3) 0.1882(2) 0.0277(8) Uani 1 1 d .
H22A H 0.6228 0.2292 0.2381 0.033 Uiso 1 1 calc R
C23 C 0.2329(2) 0.1205(3) 0.14121(19) 0.0231(8) Uani 1 1 d .
H23A H 0.1925 0.0949 0.0895 0.028 Uiso 1 1 calc R
C24 C 0.3411(2) 0.3070(3) 0.21025(19) 0.0246(8) Uani 1 1 d .
H24A H 0.3231 0.3975 0.2235 0.030 Uiso 1 1 calc R
H24B H 0.3355 0.2481 0.2543 0.030 Uiso 1 1 calc R
C25 C 0.0818(2) 0.1252(3) 0.1772(2) 0.0258(8) Uani 1 1 d .
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
C25 O1 C23 118.4(3)
C18 O2 C12 116.6(2)
C13 O5 C8 115.9(2)
C4 C3 C14 119.2(3)
C3 C4 C20 120.6(3)
C13 C5 C24 115.1(3)
C16 C6 C19 118.7(3)
C17 C7 C14 119.3(3)
O5 C8 C1 104.7(3)
O5 C8 C21 113.0(3)
C1 C8 C21 113.9(3)
C16 C9 C11 118.5(3)
C11 C10 C19 119.5(3)
C11 C10 C18 118.0(3)
C19 C10 C18 122.5(3)
C10 C11 C9 120.9(3)
O2 C12 C23 103.9(2)
O2 C12 C24 109.3(2)
C23 C12 C24 115.1(3)
O5 C13 C5 108.6(3)
O5 C13 C22 109.7(3)
C5 C13 C22 111.1(3)
C7 C14 C3 121.2(3)
C7 C14 Br1 119.8(3)
C3 C14 Br1 119.0(3)
C22 C15 C2 115.4(3)
C6 C16 C9 122.1(3)
C6 C16 Br2 118.8(3)
C9 C16 Br2 119.1(3)
C7 C17 C20 120.9(3)
O4 C18 O2 124.3(3)
O4 C18 C10 123.7(3)
O2 C18 C10 112.0(3)
C10 C19 C6 120.3(3)
C17 C20 C4 118.8(3)
C17 C20 C25 122.6(3)
C4 C20 C25 118.4(3)
C8 C21 C23 116.7(3)
C15 C22 C13 115.1(3)
C15 C22 Br3 110.0(2)
C13 C22 Br3 107.5(2)
O1 C23 C12 107.1(2)
O1 C23 C21 104.9(2)
C12 C23 C21 114.9(3)
C5 C24 C12 114.7(3)
O3 C25 O1 124.0(3)
O3 C25 C20 124.8(3)
O1 C25 C20 111.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C14 1.890(3)
Br2 C16 1.894(3)
Br3 C22 1.979(3)
O1 C25 1.350(4)
O1 C23 1.450(4)
O2 C18 1.330(4)
O2 C12 1.464(4)
O3 C25 1.198(4)
O4 C18 1.202(4)
O5 C13 1.426(4)
O5 C8 1.432(4)
C1 C8 1.511(5)
C2 C15 1.520(4)
C3 C4 1.372(5)
C3 C14 1.382(5)
C4 C20 1.394(4)
C5 C13 1.516(4)
C5 C24 1.529(4)
C6 C16 1.372(5)
C6 C19 1.387(4)
C7 C17 1.370(4)
C7 C14 1.374(4)
C8 C21 1.522(4)
C9 C16 1.374(5)
C9 C11 1.383(5)
C10 C11 1.379(4)
C10 C19 1.385(4)
C10 C18 1.491(4)
C12 C23 1.522(4)
C12 C24 1.533(5)
C13 C22 1.525(5)
C15 C22 1.503(5)
C17 C20 1.388(5)
C20 C25 1.478(5)
C21 C23 1.523(4)
