#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/45/1514544.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_1514544
loop_
_publ_author_name
'Hussain, Nusrah'
'Hussain, Mahmud M.'
'Carroll, Patrick J.'
'Walsh, Patrick J.'
_publ_section_title
;
 Chemo- and diastereoselective tandem dual oxidation of B(pin)-substituted
 allylic alcohols: synthesis of B(pin)-substituted epoxy alcohols,
 2-keto-anti-1,3-diols and dihydroxy-tetrahydrofuran-3-ones
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              3946
_journal_paper_doi               10.1039/c3sc51616d
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_sum            'C19 H20 Cl2 O4'
_chemical_formula_weight         383.25
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8057(5)
_cell_length_b                   10.1854(7)
_cell_length_c                   23.4262(17)
_cell_measurement_temperature    143(1)
_cell_volume                     1862.5(2)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31652
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.64(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0541
_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)+(0.0828P)²+1.3825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1540
_reflns_number_gt                3085
_reflns_number_total             3408
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc51616d.txt
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1514544
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
C1 C 0.3462(4) 0.8590(3) 0.10339(12) 0.0238(6) Uani 1 1 d .
C2 C 0.4615(4) 0.8031(3) 0.05626(12) 0.0240(6) Uani 1 1 d .
H2 H 0.5068 0.8725 0.0315 0.032 Uiso 1 1 calc R
C3 C 0.6017(4) 0.7393(3) 0.09140(12) 0.0234(6) Uani 1 1 d .
C4 C 0.5299(4) 0.7130(3) 0.15101(12) 0.0223(6) Uani 1 1 d .
H4 H 0.5966 0.7615 0.1795 0.030 Uiso 1 1 calc R
C5 C 0.1578(4) 0.8633(3) 0.08750(12) 0.0251(6) Uani 1 1 d .
H5 H 0.1187 0.7738 0.0795 0.033 Uiso 1 1 calc R
C6 C 0.0485(4) 0.9205(3) 0.13545(13) 0.0261(7) Uani 1 1 d .
C7 C 0.0110(5) 1.0543(3) 0.13719(15) 0.0373(8) Uani 1 1 d .
H7 H 0.0472 1.1086 0.1076 0.050 Uiso 1 1 calc R
C8 C -0.0795(5) 1.1069(4) 0.18253(17) 0.0486(10) Uani 1 1 d .
H8 H -0.1019 1.1965 0.1836 0.065 Uiso 1 1 calc R
C9 C -0.1371(5) 1.0269(4) 0.22633(16) 0.0483(10) Uani 1 1 d .
H9 H -0.1976 1.0623 0.2569 0.064 Uiso 1 1 calc R
C10 C -0.1038(5) 0.8942(4) 0.22411(15) 0.0429(9) Uani 1 1 d .
H10 H -0.1439 0.8397 0.2530 0.057 Uiso 1 1 calc R
C11 C -0.0108(4) 0.8407(4) 0.17908(13) 0.0332(7) Uani 1 1 d .
H11 H 0.0116 0.7511 0.1783 0.044 Uiso 1 1 calc R
C12 C 0.4200(4) 0.9912(3) 0.12266(14) 0.0295(7) Uani 1 1 d .
H12a H 0.3661 1.0177 0.1577 0.044 Uiso 1 1 calc R
H12b H 0.3989 1.0562 0.0938 0.044 Uiso 1 1 calc R
H12c H 0.5412 0.9827 0.1286 0.044 Uiso 1 1 calc R
C13 C 0.5281(4) 0.5690(3) 0.16593(12) 0.0236(6) Uani 1 1 d .
C14 C 0.4116(4) 0.4853(3) 0.13981(14) 0.0299(7) Uani 1 1 d .
H14 H 0.3342 0.5179 0.1132 0.040 Uiso 1 1 calc R
C15 C 0.4108(5) 0.3527(3) 0.15360(15) 0.0343(8) Uani 1 1 d .
H15 H 0.3342 0.2963 0.1356 0.046 Uiso 1 1 calc R
C16 C 0.5222(5) 0.3046(3) 0.19347(15) 0.0346(8) Uani 1 1 d .
H16 H 0.5188 0.2161 0.2032 0.046 Uiso 1 1 calc R
C17 C 0.6396(5) 0.3861(3) 0.21937(13) 0.0335(7) Uani 1 1 d .
H17 H 0.7167 0.3524 0.2459 0.045 Uiso 1 1 calc R
C18 C 0.6426(4) 0.5189(3) 0.20582(13) 0.0282(7) Uani 1 1 d .
H18 H 0.7211 0.5743 0.2234 0.038 Uiso 1 1 calc R
O1 O 0.3601(3) 0.76251(19) 0.14918(8) 0.0230(4) Uani 1 1 d .
O2 O 0.1470(3) 0.9384(2) 0.03656(9) 0.0288(5) Uani 1 1 d .
H2a H 0.0521 0.9286 0.0222 0.043 Uiso 1 1 calc R
O3 O 0.3867(3) 0.6999(2) 0.02421(9) 0.0287(5) Uani 1 1 d .
H3 H 0.3256 0.7309 -0.0009 0.043 Uiso 1 1 calc R
O4 O 0.7453(3) 0.7133(2) 0.07596(9) 0.0303(5) Uani 1 1 d .
C19 C 0.8011(6) 0.3520(6) 0.0545(2) 0.0834(18) Uani 1 1 d D
H19a H 0.7365 0.4206 0.0355 0.111 Uiso 1 1 calc R
H19b H 0.7290 0.3149 0.0841 0.111 Uiso 1 1 calc R
Cl1 Cl 0.9824(2) 0.42036(16) 0.08561(9) 0.1003(6) Uani 1 1 d D
Cl2 Cl 0.8522(3) 0.2297(2) 0.00505(8) 0.1031(6) Uani 1 1 d 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'
Cl Cl 0.1484 0.1585 '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
O1 C1 C5 105.8(2)
O1 C1 C12 110.3(2)
C5 C1 C12 114.3(2)
O1 C1 C2 103.6(2)
C5 C1 C2 113.8(2)
C12 C1 C2 108.5(3)
O3 C2 C3 105.5(2)
O3 C2 C1 114.5(2)
C3 C2 C1 101.1(2)
O4 C3 C2 127.0(3)
O4 C3 C4 125.2(3)
C2 C3 C4 107.9(2)
O1 C4 C13 110.1(2)
O1 C4 C3 104.6(2)
C13 C4 C3 112.7(2)
O2 C5 C1 106.2(2)
O2 C5 C6 112.4(2)
C1 C5 C6 111.9(2)
C11 C6 C7 118.8(3)
C11 C6 C5 120.4(3)
C7 C6 C5 120.7(3)
C8 C7 C6 120.5(4)
C7 C8 C9 120.5(4)
C10 C9 C8 119.2(3)
C9 C10 C11 120.8(4)
C6 C11 C10 120.3(3)
C14 C13 C18 119.5(3)
C14 C13 C4 120.1(3)
C18 C13 C4 120.4(3)
C13 C14 C15 119.8(3)
C16 C15 C14 120.3(3)
C15 C16 C17 120.6(3)
C16 C17 C18 119.8(3)
C17 C18 C13 120.0(3)
C4 O1 C1 109.4(2)
Cl1 C19 Cl2 112.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.459(3)
C1 C5 1.518(4)
C1 C12 1.533(4)
C1 C2 1.534(4)
C2 O3 1.418(4)
C2 C3 1.516(4)
C3 O4 1.207(4)
C3 C4 1.528(4)
C4 O1 1.418(4)
C4 C13 1.508(4)
C5 O2 1.419(3)
C5 C6 1.526(4)
C6 C11 1.385(5)
C6 C7 1.395(5)
C7 C8 1.384(5)
C8 C9 1.385(6)
C9 C10 1.377(6)
C10 C11 1.391(5)
C13 C14 1.389(5)
C13 C18 1.390(4)
C14 C15 1.389(5)
C15 C16 1.367(5)
C16 C17 1.377(5)
C17 C18 1.390(5)
C19 Cl1 1.737(6)
C19 Cl2 1.747(6)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O3 0.82 2.14 2.853(3) 146.1 2_465
O3 H3 O4 0.82 1.95 2.739(3) 160.9 2_465
