#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:32:06 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178874 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/03/4110307.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_4110307
loop_
_publ_author_name
'Luca Salvi'
'Sang-Jin Jeon'
'Ethan L. Fisher'
'Patrick J. Carroll'
'Patrick J. Walsh'
_publ_section_title
;
 Catalytic Asymmetric Generation of (Z)-Disubstituted Allylic Alcohols
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16119
_journal_page_last               16125
_journal_paper_doi               10.1021/ja0762285
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C25 H26 O4'
_chemical_formula_weight         390.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.167(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.631(3)
_cell_length_b                   6.1265(13)
_cell_length_c                   13.649(3)
_cell_measurement_temperature    143(1)
_cell_volume                     1056.0(4)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4760
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7678
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.6(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         2967
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0437
_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)+(0.0407P)²+0.1112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                2538
_reflns_number_total             2967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0762285si20070817_064548.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4110307
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
C1 C 0.1932(2) 0.5140(5) 0.56527(19) 0.0309(7) Uani 1 1 d .
C2 C 0.2235(2) 0.7517(5) 0.57106(18) 0.0289(6) Uani 1 1 d .
C3 C 0.1200(2) 0.8712(5) 0.53987(18) 0.0329(7) Uani 1 1 d .
H3A H 0.0606 0.8190 0.5773 0.044 Uiso 1 1 calc R
H3B H 0.1269 1.0276 0.5493 0.044 Uiso 1 1 calc R
C4 C 0.10488(19) 0.8154(5) 0.42985(19) 0.0305(7) Uani 1 1 d .
H4A H 0.0380 0.7420 0.4170 0.041 Uiso 1 1 calc R
H4B H 0.1089 0.9448 0.3892 0.041 Uiso 1 1 calc R
C5 C 0.19884(19) 0.6632(4) 0.41402(18) 0.0248(6) Uani 1 1 d .
C6 C 0.29050(18) 0.7670(5) 0.47617(17) 0.0249(6) Uani 1 1 d .
C7 C 0.2735(2) 0.8255(5) 0.66706(19) 0.0408(8) Uani 1 1 d .
H7A H 0.2258 0.7972 0.7194 0.061 Uiso 1 1 calc R
H7B H 0.2882 0.9790 0.6640 0.061 Uiso 1 1 calc R
H7C H 0.3384 0.7470 0.6787 0.061 Uiso 1 1 calc R
C8 C 0.39050(19) 0.6233(5) 0.4797(2) 0.0355(7) Uani 1 1 d .
H8A H 0.4209 0.6181 0.4159 0.053 Uiso 1 1 calc R
H8B H 0.3720 0.4783 0.4998 0.053 Uiso 1 1 calc R
H8C H 0.4410 0.6838 0.5257 0.053 Uiso 1 1 calc R
C9 C 0.3211(2) 0.9980(5) 0.44860(19) 0.0318(7) Uani 1 1 d .
H9A H 0.3658 1.0589 0.4993 0.048 Uiso 1 1 calc R
H9B H 0.2583 1.0853 0.4410 0.048 Uiso 1 1 calc R
H9C H 0.3584 0.9959 0.3881 0.048 Uiso 1 1 calc R
C10 C 0.22437(19) 0.5988(5) 0.31080(19) 0.0276(6) Uani 1 1 d .
C11 C 0.2660(2) 0.7544(5) 0.15504(17) 0.0311(7) Uani 1 1 d .
H11 H 0.2237 0.6383 0.1241 0.041 Uiso 1 1 calc R
C12 C 0.3830(2) 0.7013(5) 0.14900(18) 0.0295(7) Uani 1 1 d .
C13 C 0.4585(2) 0.8482(6) 0.18547(19) 0.0408(8) Uani 1 1 d .
H13 H 0.4371 0.9785 0.2139 0.054 Uiso 1 1 calc R
C14 C 0.5659(2) 0.7993(6) 0.1793(2) 0.0494(9) Uani 1 1 d .
H14 H 0.6161 0.8962 0.2046 0.066 Uiso 1 1 calc R
C15 C 0.5980(2) 0.6076(7) 0.1359(2) 0.0453(8) Uani 1 1 d .
H15 H 0.6698 0.5761 0.1313 0.060 Uiso 1 1 calc R
C16 C 0.5235(2) 0.4629(6) 0.0993(2) 0.0421(8) Uani 1 1 d .
H16 H 0.5450 0.3342 0.0696 0.056 Uiso 1 1 calc R
C17 C 0.4168(2) 0.5092(5) 0.10668(19) 0.0347(7) Uani 1 1 d .
H17 H 0.3670 0.4096 0.0828 0.046 Uiso 1 1 calc R
C18 C 0.2378(2) 0.9703(5) 0.11066(19) 0.0355(7) Uani 1 1 d .
H18 H 0.2606 1.0926 0.1455 0.047 Uiso 1 1 calc R
C19 C 0.1841(2) 1.0093(6) 0.0274(2) 0.0374(7) Uani 1 1 d .
H19 H 0.1721 1.1559 0.0132 0.050 Uiso 1 1 calc R
C20 C 0.1412(2) 0.8544(5) -0.04505(19) 0.0355(7) Uani 1 1 d .
C21 C 0.0472(2) 0.9079(6) -0.0960(2) 0.0462(9) Uani 1 1 d .
H21 H 0.0148 1.0414 -0.0842 0.061 Uiso 1 1 calc R
C22 C 0.0020(2) 0.7668(7) -0.1632(2) 0.0505(9) Uani 1 1 d .
H22 H -0.0608 0.8050 -0.1955 0.067 Uiso 1 1 calc R
C23 C 0.0492(2) 0.5689(6) -0.1829(2) 0.0476(10) Uani 1 1 d .
H23 H 0.0178 0.4728 -0.2275 0.063 Uiso 1 1 calc R
C24 C 0.1434(2) 0.5149(6) -0.13593(19) 0.0407(8) Uani 1 1 d .
H24 H 0.1765 0.3832 -0.1498 0.054 Uiso 1 1 calc R
C25 C 0.1887(2) 0.6571(5) -0.06801(18) 0.0345(8) Uani 1 1 d .
H25 H 0.2524 0.6193 -0.0371 0.046 Uiso 1 1 calc R
O1 O 0.17530(13) 0.4639(3) 0.46868(12) 0.0287(5) Uani 1 1 d .
O2 O 0.18163(16) 0.3805(4) 0.62859(14) 0.0450(6) Uani 1 1 d .
O3 O 0.23622(13) 0.7811(3) 0.25758(12) 0.0310(5) Uani 1 1 d .
O4 O 0.23316(15) 0.4161(3) 0.28016(13) 0.0374(5) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C1 O1 121.4(3)
O2 C1 C2 130.9(3)
O1 C1 C2 107.7(2)
C1 C2 C7 115.8(2)
C1 C2 C3 103.3(2)
C7 C2 C3 115.6(2)
C1 C2 C6 99.0(2)
C7 C2 C6 118.4(2)
C3 C2 C6 102.22(19)
C4 C3 C2 104.4(2)
C5 C4 C3 101.0(2)
O1 C5 C10 107.9(2)
O1 C5 C4 105.68(19)
C10 C5 C4 118.3(2)
O1 C5 C6 102.68(19)
C10 C5 C6 116.50(19)
C4 C5 C6 104.2(2)
C9 C6 C8 109.2(2)
C9 C6 C5 115.9(2)
C8 C6 C5 112.6(2)
C9 C6 C2 114.0(2)
C8 C6 C2 113.4(2)
C5 C6 C2 91.03(18)
O4 C10 O3 125.1(2)
O4 C10 C5 126.4(3)
O3 C10 C5 108.5(2)
O3 C11 C18 102.9(2)
O3 C11 C12 110.2(2)
C18 C11 C12 113.1(2)
C17 C12 C13 118.9(3)
C17 C12 C11 121.0(3)
C13 C12 C11 120.1(3)
C14 C13 C12 119.9(3)
C15 C14 C13 120.2(3)
C16 C15 C14 119.9(3)
C15 C16 C17 120.0(3)
C16 C17 C12 121.0(3)
C19 C18 C11 128.1(3)
C18 C19 C20 129.3(3)
C25 C20 C21 117.2(3)
C25 C20 C19 124.1(3)
C21 C20 C19 118.7(3)
C22 C21 C20 121.3(3)
C21 C22 C23 120.5(3)
C22 C23 C24 119.4(3)
C23 C24 C25 120.0(3)
C24 C25 C20 121.5(3)
C1 O1 C5 105.8(2)
C10 O3 C11 117.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.201(3)
C1 O1 1.368(3)
C1 C2 1.508(4)
C2 C7 1.512(4)
C2 C3 1.551(4)
C2 C6 1.564(3)
C3 C4 1.548(4)
C4 C5 1.528(3)
C5 O1 1.465(3)
C5 C10 1.504(3)
C5 C6 1.557(3)
C6 C9 1.516(4)
C6 C8 1.540(4)
C10 O4 1.201(3)
C10 O3 1.343(3)
C11 O3 1.466(3)
C11 C18 1.495(4)
C11 C12 1.517(4)
C12 C17 1.382(4)
C12 C13 1.395(4)
C13 C14 1.394(4)
C14 C15 1.381(5)
C15 C16 1.379(4)
C16 C17 1.383(4)
C18 C19 1.333(4)
C19 C20 1.467(4)
C20 C25 1.389(4)
C20 C21 1.402(4)
C21 C22 1.376(5)
C22 C23 1.380(5)
C23 C24 1.381(4)
C24 C25 1.387(4)
