#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:37:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178908 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/37/4113770.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_4113770
loop_
_publ_author_name
'Do Hyun Ryu'
'E. J. Corey'
_publ_section_title
;
 Triflimide Activation of a Chiral Oxazaborolidine Leads to a More General
 Catalytic System for Enantioselective Diels-Alder Addition
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6388
_journal_page_last               6390
_journal_paper_doi               10.1021/ja035393r
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C14 H15 I O2'
_chemical_formula_weight         342.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.293(2)
_cell_length_b                   8.293(2)
_cell_length_c                   39.167(14)
_cell_measurement_temperature    213(2)
_cell_volume                     2693.7(13)
_computing_cell_refinement       'SMART (BRUKER, V5.054, 1998)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.01, 1999)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 1998, V5.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            17492
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_T_max  0.942203
_exptl_absorpt_correction_T_min  0.581968
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.522
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0481P)²+5.4174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                3146
_reflns_number_total             3290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja035393rsi20030331_043851.cif
_cod_data_source_block           ejc42
_cod_original_cell_volume        2693.9(13)
_cod_database_code               4113770
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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
I1 I 0.46621(6) -0.37680(4) 0.129291(11) 0.05403(15) Uani 1 1 d .
O1 O 0.5291(11) -0.2296(6) 0.19930(13) 0.099(3) Uani 1 1 d .
O2 O 0.4116(9) 0.2614(5) 0.11528(10) 0.082(2) Uani 1 1 d .
C1 C 0.4749(6) -0.1359(6) 0.14456(13) 0.0353(10) Uani 1 1 d .
C2 C 0.5061(8) -0.1139(7) 0.18161(14) 0.0481(14) Uani 1 1 d .
C3 C 0.5240(7) 0.0549(6) 0.19663(12) 0.0366(10) Uani 1 1 d .
C4 C 0.4156(8) 0.0584(8) 0.22926(14) 0.0485(14) Uani 1 1 d .
H4 H 0.4485 -0.0267 0.2456 0.058 Uiso 1 1 calc R
C5 C 0.2472(9) 0.0317(10) 0.21731(19) 0.068(2) Uani 1 1 d .
H5 H 0.1839 -0.0557 0.2246 0.082 Uiso 1 1 calc R
C6 C 0.1941(8) 0.1419(11) 0.19548(17) 0.0623(18) Uani 1 1 d .
H6 H 0.0903 0.1384 0.1859 0.075 Uiso 1 1 calc R
C7 C 0.3119(7) 0.2717(7) 0.18737(13) 0.0394(11) Uani 1 1 d .
H7 H 0.2663 0.3499 0.1709 0.047 Uiso 1 1 calc R
C8 C 0.4662(7) 0.1916(5) 0.17306(11) 0.0317(9) Uani 1 1 d .
H8 H 0.5512 0.2753 0.1738 0.038 Uiso 1 1 calc R
C9 C 0.4415(8) 0.1517(6) 0.13550(12) 0.0432(13) Uani 1 1 d .
C10 C 0.4513(6) -0.0150(6) 0.12228(12) 0.0327(9) Uani 1 1 d .
C11 C 0.4254(8) 0.2264(8) 0.24601(14) 0.0575(17) Uani 1 1 d .
H11A H 0.5374 0.2503 0.2522 0.069 Uiso 1 1 calc R
H11B H 0.3606 0.2278 0.2669 0.069 Uiso 1 1 calc R
C12 C 0.3622(9) 0.3557(8) 0.22098(15) 0.0538(15) Uani 1 1 d .
H12A H 0.4467 0.4355 0.2164 0.065 Uiso 1 1 calc R
H12B H 0.2695 0.4117 0.2310 0.065 Uiso 1 1 calc R
C13 C 0.7026(8) 0.0728(8) 0.20574(16) 0.0507(15) Uani 1 1 d .
H13A H 0.7333 -0.0115 0.2216 0.076 Uiso 1 1 calc R
H13B H 0.7206 0.1773 0.2162 0.076 Uiso 1 1 calc R
H13C H 0.7672 0.0638 0.1852 0.076 Uiso 1 1 calc R
C14 C 0.4196(8) -0.0324(7) 0.08520(12) 0.0450(13) Uani 1 1 d .
H14A H 0.5200 -0.0543 0.0734 0.068 Uiso 1 1 calc R
H14B H 0.3728 0.0665 0.0765 0.068 Uiso 1 1 calc R
H14C H 0.3452 -0.1210 0.0815 0.068 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'
I I -0.4742 1.8119 '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
C10 C1 C2 124.6(5)
C10 C1 I1 121.6(4)
C2 C1 I1 113.8(4)
O1 C2 C1 119.6(5)
O1 C2 C3 119.7(5)
C1 C2 C3 120.4(4)
C2 C3 C13 105.8(5)
C2 C3 C8 114.5(4)
C13 C3 C8 111.7(5)
C2 C3 C4 106.1(5)
C13 C3 C4 111.4(4)
C8 C3 C4 107.3(4)
C5 C4 C11 108.5(6)
C5 C4 C3 106.2(5)
C11 C4 C3 109.5(5)
C5 C4 H4 110.8
C11 C4 H4 110.8
C3 C4 H4 110.8
C6 C5 C4 114.3(6)
C6 C5 H5 122.9
C4 C5 H5 122.9
C5 C6 C7 114.7(6)
C5 C6 H6 122.6
C7 C6 H6 122.6
C6 C7 C8 108.1(5)
C6 C7 C12 108.7(5)
C8 C7 C12 106.2(5)
C6 C7 H7 111.2
C8 C7 H7 111.2
C12 C7 H7 111.2
C9 C8 C3 117.5(4)
C9 C8 C7 109.4(5)
C3 C8 C7 110.9(4)
C9 C8 H8 106.1
C3 C8 H8 106.1
C7 C8 H8 106.1
O2 C9 C10 118.5(4)
O2 C9 C8 119.2(5)
C10 C9 C8 122.3(4)
C1 C10 C9 118.6(4)
C1 C10 C14 126.1(4)
C9 C10 C14 115.1(4)
C4 C11 C12 109.9(5)
C4 C11 H11A 109.7
C12 C11 H11A 109.7
C4 C11 H11B 109.7
C12 C11 H11B 109.7
H11A C11 H11B 108.2
C11 C12 C7 108.6(5)
C11 C12 H12A 110.0
C7 C12 H12A 110.0
C11 C12 H12B 110.0
C7 C12 H12B 110.0
H12A C12 H12B 108.4
C3 C13 H13A 109.5
C3 C13 H13B 109.5
H13A C13 H13B 109.5
C3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C10 C14 H14A 109.5
C10 C14 H14B 109.5
H14A C14 H14B 109.5
C10 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.087(5)
O1 C2 1.199(7)
O2 C9 1.231(6)
C1 C10 1.343(7)
C1 C2 1.485(7)
C2 C3 1.526(8)
C3 C13 1.531(8)
C3 C8 1.539(6)
C3 C4 1.563(8)
C4 C5 1.490(9)
C4 C11 1.542(9)
C4 H4 0.9900
C5 C6 1.327(11)
C5 H5 0.9400
C6 C7 1.488(10)
C6 H6 0.9400
C7 C8 1.547(7)
C7 C12 1.547(8)
C7 H7 0.9900
C8 C9 1.522(6)
C8 H8 0.9900
C9 C10 1.479(7)
C10 C14 1.483(6)
C11 C12 1.544(9)
C11 H11A 0.9800
C11 H11B 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C13 H13A 0.9700
C13 H13B 0.9700
C13 H13C 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
C14 H14C 0.9700
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
C10 C1 C2 O1 -178.4(7)
I1 C1 C2 O1 2.6(9)
C10 C1 C2 C3 -3.9(9)
I1 C1 C2 C3 177.1(4)
O1 C2 C3 C13 65.5(8)
C1 C2 C3 C13 -109.0(6)
O1 C2 C3 C8 -171.0(7)
C1 C2 C3 C8 14.5(8)
O1 C2 C3 C4 -52.9(8)
C1 C2 C3 C4 132.6(5)
C2 C3 C4 C5 -62.5(6)
C13 C3 C4 C5 -177.2(5)
C8 C3 C4 C5 60.3(6)
C2 C3 C4 C11 -179.5(5)
C13 C3 C4 C11 65.8(6)
C8 C3 C4 C11 -56.7(6)
C11 C4 C5 C6 57.8(8)
C3 C4 C5 C6 -59.9(9)
C4 C5 C6 C7 -0.6(10)
C5 C6 C7 C8 57.3(8)
C5 C6 C7 C12 -57.5(8)
C2 C3 C8 C9 -15.8(7)
C13 C3 C8 C9 104.5(6)
C4 C3 C8 C9 -133.2(5)
C2 C3 C8 C7 111.0(5)
C13 C3 C8 C7 -128.7(5)
C4 C3 C8 C7 -6.4(6)
C6 C7 C8 C9 80.9(5)
C12 C7 C8 C9 -162.6(5)
C6 C7 C8 C3 -50.3(6)
C12 C7 C8 C3 66.2(6)
C3 C8 C9 O2 -172.5(7)
C7 C8 C9 O2 59.9(8)
C3 C8 C9 C10 7.8(9)
C7 C8 C9 C10 -119.8(6)
C2 C1 C10 C9 -5.5(8)
I1 C1 C10 C9 173.4(4)
C2 C1 C10 C14 -179.9(6)
I1 C1 C10 C14 -1.0(8)
O2 C9 C10 C1 -176.3(6)
C8 C9 C10 C1 3.4(9)
O2 C9 C10 C14 -1.3(9)
C8 C9 C10 C14 178.4(5)
C5 C4 C11 C12 -54.2(7)
C3 C4 C11 C12 61.4(7)
C4 C11 C12 C7 -0.5(8)
C6 C7 C12 C11 54.8(7)
C8 C7 C12 C11 -61.3(6)
