#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/25/4102586.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_4102586
loop_
_publ_author_name
'Ilija Čorić'
'Sreekumar Vellalath'
'Benjamin List'
_publ_section_title
;
 Catalytic Asymmetric Transacetalization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8536
_journal_page_last               8537
_journal_paper_doi               10.1021/ja102753d
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        dichloromethane
_chemical_formula_moiety         'C18 H18 Br2 O2'
_chemical_formula_sum            'C18 H18 Br2 O2'
_chemical_formula_weight         426.14
_chemical_name_systematic
;
 2-(R)-ethoxy-5,5-di(4-bromophenyl)tetrahydrofuran
;
_space_group_IT_number           76
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      76
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                COL-CB-129-14
_audit_creation_date             2010-02-11
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8373(9)
_cell_length_b                   10.8373(9)
_cell_length_c                   14.8921(13)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.0603
_cell_measurement_theta_min      4.0792
_cell_volume                     1749.0(3)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.08
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0196
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            40020
_diffrn_reflns_theta_full        66.52
_diffrn_reflns_theta_max         66.52
_diffrn_reflns_theta_min         4.08
_exptl_absorpt_coefficient_mu    5.909
_exptl_absorpt_correction_T_max  0.70728
_exptl_absorpt_correction_T_min  0.10636
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.973
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.018(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0168
_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)+(0.0152P)²+0.6923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0407
_refine_ls_wR_factor_ref         0.0407
_reflns_number_gt                3046
_reflns_number_total             3048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja102753d_si_001.cif
_cod_data_source_block           6855
_cod_original_sg_symbol_Hall     'p 4w'
_cod_database_code               4102586
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'
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 0.08715(2) -0.355746(18) 1.115331(17) 0.03323(7) Uani 1 1 d .
Br2 Br 0.32900(2) 0.14519(2) 0.597045(15) 0.03647(7) Uani 1 1 d .
C1 C 0.26440(18) 0.16907(18) 1.01050(16) 0.0223(4) Uani 1 1 d .
C2 C 0.18048(19) 0.27432(19) 1.04425(16) 0.0263(5) Uani 1 1 d .
H2A H 0.1768 0.3429 1.0004 0.032 Uiso 1 1 calc R
H2B H 0.0958 0.2444 1.0564 0.032 Uiso 1 1 calc R
C3 C 0.2454(2) 0.31360(18) 1.13057(16) 0.0284(5) Uani 1 1 d .
H3A H 0.2255 0.4000 1.1466 0.034 Uiso 1 1 calc R
H3B H 0.2235 0.2589 1.1814 0.034 Uiso 1 1 calc R
C4 C 0.37882(18) 0.29970(17) 1.10473(16) 0.0242(4) Uani 1 1 d .
H4 H 0.4317 0.2903 1.1593 0.029 Uiso 1 1 calc R
C5 C 0.5412(2) 0.4053(2) 1.02957(19) 0.0326(5) Uani 1 1 d .
H5A H 0.5549 0.3467 0.9796 0.039 Uiso 1 1 calc R
H5B H 0.5932 0.3796 1.0809 0.039 Uiso 1 1 calc R
C6 C 0.5751(2) 0.5339(2) 1.0007(2) 0.0381(6) Uani 1 1 d .
H6A H 0.5266 0.5567 0.9476 0.057 Uiso 1 1 calc R
H6B H 0.6631 0.5370 0.9859 0.057 Uiso 1 1 calc R
H6C H 0.5575 0.5918 1.0496 0.057 Uiso 1 1 calc R
C7 C 0.27968(19) 0.16641(18) 0.90887(16) 0.0227(4) Uani 1 1 d .
C8 C 0.39146(18) 0.12881(18) 0.87131(16) 0.0238(4) Uani 1 1 d .
H8 H 0.4584 0.1076 0.9095 0.029 Uiso 1 1 calc R
C9 C 0.4060(2) 0.12200(19) 0.77876(16) 0.0272(5) Uani 1 1 d .
H9 H 0.4821 0.0959 0.7535 0.033 Uiso 1 1 calc R
C10 C 0.3082(2) 0.15373(19) 0.72411(16) 0.0282(5) Uani 1 1 d .
C11 C 0.1959(2) 0.1907(2) 0.75886(17) 0.0306(5) Uani 1 1 d .
H11 H 0.1294 0.2120 0.7203 0.037 Uiso 1 1 calc R
C12 C 0.18288(18) 0.19605(18) 0.85193(18) 0.0274(5) Uani 1 1 d .
H12 H 0.1060 0.2205 0.8769 0.033 Uiso 1 1 calc R
C13 C 0.21977(18) 0.04190(18) 1.04201(14) 0.0203(4) Uani 1 1 d .
C14 C 0.29587(18) -0.03736(18) 1.09020(15) 0.0244(4) Uani 1 1 d .
H14 H 0.3763 -0.0111 1.1068 0.029 Uiso 1 1 calc R
C15 C 0.25555(19) -0.15471(18) 1.11438(16) 0.0263(4) Uani 1 1 d .
H15 H 0.3079 -0.2086 1.1472 0.032 Uiso 1 1 calc R
C16 C 0.1389(2) -0.19143(17) 1.09006(14) 0.0246(4) Uani 1 1 d .
C17 C 0.06002(19) -0.11411(19) 1.04357(15) 0.0256(4) Uani 1 1 d .
H17 H -0.0210 -0.1403 1.0285 0.031 Uiso 1 1 calc R
C18 C 0.10111(19) 0.00148(19) 1.01948(15) 0.0249(4) Uani 1 1 d .
H18 H 0.0479 0.0548 0.9869 0.030 Uiso 1 1 calc R
O1 O 0.38370(12) 0.19130(12) 1.05079(11) 0.0227(3) Uani 1 1 d .
O2 O 0.41370(13) 0.40504(13) 1.05517(11) 0.0251(3) 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.0300
0.00 -1.00 0.00 0.0300
1.00 0.00 0.00 0.1020
-1.00 0.00 0.00 0.0920
0.00 0.00 1.00 0.3700
0.00 1.00 -1.00 0.2620
1.00 -1.00 -1.00 0.2450
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C7 108.57(16) y
O1 C1 C13 107.74(16) y
C7 C1 C13 108.74(17) y
O1 C1 C2 105.59(17) y
C7 C1 C2 113.69(17) y
C13 C1 C2 112.25(17) y
C3 C2 C1 102.06(17) y
C4 C3 C2 101.53(18) y
O2 C4 O1 111.24(18) y
O2 C4 C3 108.08(16) y
O1 C4 C3 105.23(16) y
O2 C5 C6 108.22(18) y
C12 C7 C8 118.6(2) y
C12 C7 C1 121.41(19) y
C8 C7 C1 119.90(19) y
C9 C8 C7 120.8(2) y
C10 C9 C8 119.0(2) y
C9 C10 C11 121.8(2) y
C9 C10 Br2 118.83(18) y
C11 C10 Br2 119.32(18) y
C10 C11 C12 118.3(2) y
C7 C12 C11 121.4(2) y
C14 C13 C18 118.39(18) y
C14 C13 C1 121.73(18) y
C18 C13 C1 119.84(18) y
C13 C14 C15 120.78(19) y
C16 C15 C14 119.03(19) y
C15 C16 C17 121.70(18) y
C15 C16 Br1 119.33(16) y
C17 C16 Br1 118.89(15) y
C18 C17 C16 118.79(19) y
C17 C18 C13 121.3(2) y
C4 O1 C1 109.78(14) y
C4 O2 C5 113.50(15) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C16 1.9047(19) y
Br2 C10 1.908(2) y
C1 O1 1.446(2) y
C1 C7 1.523(3) y
C1 C13 1.534(3) y
C1 C2 1.543(3) y
C2 C3 1.526(3) y
C3 C4 1.504(3) y
C4 O2 1.411(3) y
C4 O1 1.424(3) y
C5 O2 1.434(3) y
C5 C6 1.504(3) y
C7 C12 1.387(3) y
C7 C8 1.395(3) y
C8 C9 1.389(4) y
C9 C10 1.379(3) y
C10 C11 1.382(3) y
C11 C12 1.394(4) y
C13 C14 1.390(3) y
C13 C18 1.399(3) y
C14 C15 1.392(3) y
C15 C16 1.374(3) y
C16 C17 1.383(3) y
C17 C18 1.377(3) y
