#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:03:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178418 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023927.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_4023927
loop_
_publ_author_name
'T. Andrew Mitchell'
'Cunxiang Zhao'
'Daniel Romo'
_publ_section_title
;
 Diastereoselective, Three-Component Cascade Synthesis of
 Tetrahydrofurans and Tetrahydropyrans Employing the Tandem
 Mukaiyama Aldol--Lactonization Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9544
_journal_page_last               9551
_journal_paper_doi               10.1021/jo801604k
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C22 H25 Br O4'
_chemical_formula_weight         433.33
_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                 115.272(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.996(16)
_cell_length_b                   5.709(5)
_cell_length_c                   20.557(17)
_cell_measurement_reflns_used    5789
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.19
_cell_volume                     2016(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0709
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20029
_diffrn_reflns_theta_full        27.64
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    2.063
_exptl_absorpt_correction_T_max  0.8203
_exptl_absorpt_correction_T_min  0.4252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0352
_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)+(0.0414P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                3050
_reflns_number_total             4500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801604k_si_002.cif
_cod_data_source_block           drb1127b
_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               4023927
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 -0.237325(14) 1.01460(5) 0.165806(13) 0.03181(10) Uani 1 1 d . . .
O4 O 0.14618(9) -0.0382(3) 0.27979(8) 0.0248(4) Uani 1 1 d . . .
O2 O 0.06200(9) 0.4169(3) 0.42166(8) 0.0236(4) Uani 1 1 d . . .
O3 O 0.24493(9) 0.3648(3) 0.41696(8) 0.0244(4) Uani 1 1 d . . .
O1 O 0.05437(9) 0.7019(3) 0.49469(8) 0.0275(4) Uani 1 1 d . . .
C1 C -0.15770(13) 0.8801(4) 0.25005(12) 0.0239(5) Uani 1 1 d . . .
C4 C -0.03829(12) 0.6950(4) 0.37085(11) 0.0210(5) Uani 1 1 d . . .
C5 C -0.06648(13) 0.5724(4) 0.30565(12) 0.0224(5) Uani 1 1 d . . .
H5 H -0.0443 0.4255 0.3030 0.027 Uiso 1 1 calc R . .
C11 C 0.18115(12) 0.2019(4) 0.39016(11) 0.0202(5) Uani 1 1 d . . .
H11 H 0.1345 0.2845 0.3538 0.024 Uiso 1 1 calc R . .
C18 C 0.04440(14) -0.4535(5) 0.17863(13) 0.0276(6) Uani 1 1 d . . .
H18 H 0.0848 -0.5527 0.2099 0.033 Uiso 1 1 calc R . .
C6 C -0.12655(13) 0.6644(4) 0.24497(12) 0.0238(5) Uani 1 1 d . . .
H6 H -0.1461 0.5816 0.2007 0.029 Uiso 1 1 calc R . .
C7 C 0.02971(13) 0.6088(4) 0.43617(12) 0.0224(5) Uani 1 1 d . . .
C17 C 0.03021(13) -0.2385(4) 0.20390(12) 0.0235(5) Uani 1 1 d . . .
C9 C 0.16229(13) 0.1231(4) 0.45208(11) 0.0223(5) Uani 1 1 d . . .
H9 H 0.1198 0.0039 0.4326 0.027 Uiso 1 1 calc R . .
C16 C 0.08008(13) -0.1595(5) 0.27952(12) 0.0288(6) Uani 1 1 d . . .
H16A H 0.0500 -0.0544 0.2965 0.035 Uiso 1 1 calc R . .
H16B H 0.0974 -0.2966 0.3121 0.035 Uiso 1 1 calc R . .
C13 C 0.27625(13) 0.1100(5) 0.34515(12) 0.0275(6) Uani 1 1 d . . .
H13A H 0.3245 0.0318 0.3790 0.033 Uiso 1 1 calc R . .
H13B H 0.2719 0.0924 0.2957 0.033 Uiso 1 1 calc R . .
C20 C -0.06022(15) -0.3797(5) 0.06282(13) 0.0324(6) Uani 1 1 d . . .
H20 H -0.0909 -0.4275 0.0146 0.039 Uiso 1 1 calc R . .
C14 C 0.27649(13) 0.3677(4) 0.36433(12) 0.0247(5) Uani 1 1 d . . .
H14 H 0.2408 0.4570 0.3209 0.030 Uiso 1 1 calc R . .
C22 C -0.03040(14) -0.0973(5) 0.15780(13) 0.0271(5) Uani 1 1 d . . .
H22 H -0.0408 0.0477 0.1746 0.032 Uiso 1 1 calc R . .
C3 C -0.07177(13) 0.9107(4) 0.37476(12) 0.0236(5) Uani 1 1 d . . .
H3 H -0.0530 0.9934 0.4191 0.028 Uiso 1 1 calc R . .
C8 C 0.13223(13) 0.3280(4) 0.48092(11) 0.0250(5) Uani 1 1 d . . .
H8A H 0.1201 0.2749 0.5209 0.030 Uiso 1 1 calc R . .
H8B H 0.1721 0.4527 0.4992 0.030 Uiso 1 1 calc R . .
C19 C -0.00034(14) -0.5217(4) 0.10815(13) 0.0301(6) Uani 1 1 d . . .
H19 H 0.0101 -0.6659 0.0910 0.036 Uiso 1 1 calc R . .
C21 C -0.07577(14) -0.1671(5) 0.08730(13) 0.0316(6) Uani 1 1 d . . .
H21 H -0.1171 -0.0705 0.0561 0.038 Uiso 1 1 calc R . .
C12 C 0.20503(13) 0.0061(4) 0.35104(12) 0.0225(5) Uani 1 1 d . . .
H12 H 0.2190 -0.1410 0.3802 0.027 Uiso 1 1 calc R . .
C2 C -0.13197(14) 1.0037(4) 0.31433(13) 0.0260(5) Uani 1 1 d . . .
H2 H -0.1552 1.1489 0.3168 0.031 Uiso 1 1 calc R . .
C10 C 0.23149(14) 0.0095(4) 0.51445(12) 0.0290(6) Uani 1 1 d . . .
H10A H 0.2724 0.1267 0.5374 0.043 Uiso 1 1 calc R . .
H10B H 0.2520 -0.1191 0.4960 0.043 Uiso 1 1 calc R . .
H10C H 0.2143 -0.0518 0.5498 0.043 Uiso 1 1 calc R . .
C15 C 0.35570(15) 0.4830(4) 0.39624(14) 0.0307(6) Uani 1 1 d . . .
H15A H 0.3511 0.6416 0.4123 0.046 Uiso 1 1 calc R . .
H15B H 0.3760 0.4913 0.3598 0.046 Uiso 1 1 calc R . .
H15C H 0.3913 0.3910 0.4374 0.046 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O4 C12 112.88(17) . . ?
C7 O2 C8 115.93(17) . . ?
C11 O3 C14 105.78(16) . . ?
C6 C1 C2 122.2(2) . . ?
C6 C1 Br1 119.12(18) . . ?
C2 C1 Br1 118.64(19) . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 C7 121.8(2) . . ?
C3 C4 C7 118.4(2) . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
O3 C11 C9 109.26(17) . . ?
O3 C11 C12 106.22(17) . . ?
C9 C11 C12 116.3(2) . . ?
O3 C11 H11 108.3 . . ?
C9 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
O1 C7 O2 123.8(2) . . ?
O1 C7 C4 124.6(2) . . ?
O2 C7 C4 111.64(19) . . ?
C22 C17 C18 119.2(2) . . ?
C22 C17 C16 120.2(2) . . ?
C18 C17 C16 120.6(2) . . ?
C8 C9 C11 110.9(2) . . ?
C8 C9 C10 109.16(19) . . ?
C11 C9 C10 113.47(19) . . ?
C8 C9 H9 107.7 . . ?
C11 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
O4 C16 C17 108.28(17) . . ?
O4 C16 H16A 110.0 . . ?
C17 C16 H16A 110.0 . . ?
O4 C16 H16B 110.0 . . ?
C17 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C14 C13 C12 105.04(18) . . ?
C14 C13 H13A 110.7 . . ?
C12 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
C12 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
O3 C14 C15 109.56(19) . . ?
O3 C14 C13 103.10(18) . . ?
C15 C14 C13 115.2(2) . . ?
O3 C14 H14 109.6 . . ?
C15 C14 H14 109.6 . . ?
C13 C14 H14 109.6 . . ?
C21 C22 C17 120.5(2) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
O2 C8 C9 107.59(18) . . ?
O2 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
O2 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C22 C21 C20 119.6(2) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
O4 C12 C13 108.52(18) . . ?
O4 C12 C11 112.49(18) . . ?
C13 C12 C11 103.04(18) . . ?
O4 C12 H12 110.8 . . ?
C13 C12 H12 110.8 . . ?
C11 C12 H12 110.8 . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 C1 1.908(3) . ?
O4 C16 1.432(3) . ?
O4 C12 1.436(3) . ?
O2 C7 1.350(3) . ?
O2 C8 1.461(3) . ?
O3 C11 1.438(3) . ?
O3 C14 1.444(2) . ?
O1 C7 1.212(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.390(3) . ?
C4 C5 1.400(3) . ?
C4 C3 1.404(3) . ?
C4 C7 1.494(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C11 C9 1.530(3) . ?
C11 C12 1.553(3) . ?
C11 H11 1.0000 . ?
C18 C19 1.386(3) . ?
C18 C17 1.403(3) . ?
C18 H18 0.9500 . ?
C6 H6 0.9500 . ?
C17 C22 1.394(3) . ?
C17 C16 1.503(3) . ?
C9 C8 1.528(3) . ?
C9 C10 1.534(3) . ?
C9 H9 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C13 C14 1.523(4) . ?
C13 C12 1.529(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C20 C19 1.383(4) . ?
C20 C21 1.393(4) . ?
C20 H20 0.9500 . ?
C14 C15 1.512(3) . ?
C14 H14 1.0000 . ?
C22 C21 1.391(3) . ?
C22 H22 0.9500 . ?
C3 C2 1.386(3) . ?
C3 H3 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C19 H19 0.9500 . ?
C21 H21 0.9500 . ?
C12 H12 1.0000 . ?
C2 H2 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C4 C5 C6 0.7(3) . . . . ?
C7 C4 C5 C6 -176.0(2) . . . . ?
C14 O3 C11 C9 160.62(18) . . . . ?
C14 O3 C11 C12 34.4(2) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
Br1 C1 C6 C5 177.29(16) . . . . ?
C8 O2 C7 O1 -2.3(3) . . . . ?
C8 O2 C7 C4 176.04(17) . . . . ?
C5 C4 C7 O1 -176.6(2) . . . . ?
C3 C4 C7 O1 6.6(3) . . . . ?
C5 C4 C7 O2 5.1(3) . . . . ?
C3 C4 C7 O2 -171.68(19) . . . . ?
C19 C18 C17 C22 1.4(3) . . . . ?
C19 C18 C17 C16 -178.0(2) . . . . ?
O3 C11 C9 C8 65.3(2) . . . . ?
C12 C11 C9 C8 -174.50(18) . . . . ?
O3 C11 C9 C10 -58.0(3) . . . . ?
C12 C11 C9 C10 62.2(3) . . . . ?
C12 O4 C16 C17 -168.88(19) . . . . ?
C22 C17 C16 O4 -92.3(3) . . . . ?
C18 C17 C16 O4 87.1(3) . . . . ?
C11 O3 C14 C15 -165.3(2) . . . . ?
C11 O3 C14 C13 -42.1(2) . . . . ?
C12 C13 C14 O3 33.2(2) . . . . ?
C12 C13 C14 C15 152.46(19) . . . . ?
C18 C17 C22 C21 -0.7(3) . . . . ?
C16 C17 C22 C21 178.7(2) . . . . ?
C5 C4 C3 C2 -0.6(3) . . . . ?
C7 C4 C3 C2 176.25(19) . . . . ?
C7 O2 C8 C9 -176.17(18) . . . . ?
C11 C9 C8 O2 59.7(2) . . . . ?
C10 C9 C8 O2 -174.54(17) . . . . ?
C21 C20 C19 C18 0.4(4) . . . . ?
C17 C18 C19 C20 -1.3(4) . . . . ?
C17 C22 C21 C20 -0.1(3) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C16 O4 C12 C13 173.59(19) . . . . ?
C16 O4 C12 C11 -73.1(2) . . . . ?
C14 C13 C12 O4 106.9(2) . . . . ?
C14 C13 C12 C11 -12.5(2) . . . . ?
O3 C11 C12 O4 -129.13(18) . . . . ?
C9 C11 C12 O4 109.1(2) . . . . ?
O3 C11 C12 C13 -12.5(2) . . . . ?
C9 C11 C12 C13 -134.3(2) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
Br1 C1 C2 C3 -177.17(16) . . . . ?
