#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:52:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178921 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/50/4115092.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_4115092
loop_
_publ_author_name
'Do Hyun Ryu'
'Thomas W. Lee'
'E. J. Corey'
_publ_section_title
;
 Broad-Spectrum Enantioselective Diels-Alder Catalysis by Chiral, Cationic
 Oxazaborolidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9992
_journal_page_last               9993
_journal_paper_doi               10.1021/ja027468h
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C18 H16 B Cl2 F3 O'
_chemical_formula_weight         387.02
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.035(2)
_cell_angle_beta                 93.937(2)
_cell_angle_gamma                115.123(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7770(12)
_cell_length_b                   10.1641(12)
_cell_length_c                   11.5487(14)
_cell_measurement_temperature    213(2)
_cell_volume                     927.0(2)
_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_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_method       'ω, 0.3 deg'
_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  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4992
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0741
_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)+(0.0476P)²+1.2631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                2775
_reflns_number_total             3231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja027468h_s4.cif
_cod_data_source_block           ejc24t
_cod_original_cell_volume        926.97(19)
_cod_database_code               4115092
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
B1 B 0.0433(4) 0.3249(5) 1.2572(4) 0.0364(8) Uani 1 1 d .
F1 F -0.0393(2) 0.3949(2) 1.2296(2) 0.0491(5) Uani 1 1 d .
F2 F -0.0566(2) 0.1737(2) 1.24743(18) 0.0441(5) Uani 1 1 d .
F3 F 0.1509(2) 0.4231(3) 1.37566(19) 0.0586(6) Uani 1 1 d .
O1 O 0.1399(2) 0.3035(2) 1.1595(2) 0.0332(5) Uani 1 1 d .
C1 C 0.0881(3) 0.2193(3) 1.0362(3) 0.0301(7) Uani 1 1 d .
C2 C -0.0775(3) 0.1310(4) 0.9730(3) 0.0309(7) Uani 1 1 d .
H2 H -0.1446 0.1505 1.0233 0.037 Uiso 1 1 calc R
C2S C 0.9533(6) 0.2320(6) 0.5462(4) 0.0798(15) Uani 1 1 d .
H2S1 H 0.9721 0.2067 0.4601 0.096 Uiso 1 1 calc R
H2S2 H 0.9560 0.3373 0.5788 0.096 Uiso 1 1 calc R
C3 C -0.1428(4) 0.0226(4) 0.8474(3) 0.0328(7) Uani 1 1 d .
H3 H -0.0741 0.0097 0.7966 0.039 Uiso 1 1 calc R
C4 C -0.3093(4) -0.0762(4) 0.7828(3) 0.0322(7) Uani 1 1 d .
C5 C -0.4226(4) -0.0496(4) 0.8400(3) 0.0372(7) Uani 1 1 d .
H5 H -0.3913 0.0361 0.9234 0.045 Uiso 1 1 calc R
C6 C -0.5792(4) -0.1477(4) 0.7752(4) 0.0462(9) Uani 1 1 d .
H6 H -0.6541 -0.1281 0.8145 0.055 Uiso 1 1 calc R
C7 C -0.6275(4) -0.2742(4) 0.6537(4) 0.0496(9) Uani 1 1 d .
H7 H -0.7350 -0.3410 0.6104 0.060 Uiso 1 1 calc R
C8 C -0.5183(4) -0.3033(5) 0.5951(4) 0.0553(10) Uani 1 1 d .
H8 H -0.5511 -0.3901 0.5120 0.066 Uiso 1 1 calc R
C9 C -0.3601(4) -0.2042(4) 0.6592(3) 0.0482(9) Uani 1 1 d .
H9 H -0.2859 -0.2235 0.6187 0.058 Uiso 1 1 calc R
C10 C 0.2037(3) 0.2178(4) 0.9654(3) 0.0324(7) Uani 1 1 d .
H10 H 0.1701 0.1610 0.8744 0.039 Uiso 1 1 calc R
C11 C 0.3568(3) 0.2942(4) 1.0246(3) 0.0326(7) Uani 1 1 d .
H11 H 0.3855 0.3444 1.1158 0.039 Uiso 1 1 calc R
C12 C 0.4838(3) 0.3080(4) 0.9631(3) 0.0319(7) Uani 1 1 d .
C13 C 0.6361(4) 0.3824(4) 1.0408(3) 0.0383(8) Uani 1 1 d .
H13 H 0.6542 0.4204 1.1311 0.046 Uiso 1 1 calc R
C14 C 0.7609(4) 0.4009(4) 0.9866(4) 0.0446(9) Uani 1 1 d .
H14 H 0.8629 0.4511 1.0401 0.054 Uiso 1 1 calc R
C15 C 0.7359(4) 0.3463(4) 0.8553(4) 0.0488(9) Uani 1 1 d .
H15 H 0.8209 0.3589 0.8187 0.059 Uiso 1 1 calc R
C16 C 0.5857(4) 0.2724(5) 0.7758(4) 0.0511(9) Uani 1 1 d .
H16 H 0.5690 0.2358 0.6856 0.061 Uiso 1 1 calc R
C17 C 0.4606(4) 0.2527(4) 0.8295(3) 0.0427(8) Uani 1 1 d .
H17 H 0.3588 0.2016 0.7753 0.051 Uiso 1 1 calc R
Cl1S Cl 0.7677(2) 0.08403(19) 0.53106(17) 0.1098(6) Uani 1 1 d .
Cl1 Cl 1.1006(3) 0.2473(2) 0.6477(2) 0.1536(10) 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
F3 B1 F1 111.9(3)
F3 B1 F2 111.3(3)
F1 B1 F2 111.1(3)
F3 B1 O1 105.0(3)
F1 B1 O1 109.0(3)
F2 B1 O1 108.3(3)
C1 O1 B1 127.2(2)
O1 C1 C2 121.0(3)
O1 C1 C10 116.5(3)
C2 C1 C10 122.5(3)
C3 C2 C1 124.6(3)
Cl1 C2S Cl1S 113.4(3)
C2 C3 C4 126.0(3)
C9 C4 C5 118.1(3)
C9 C4 C3 119.1(3)
C5 C4 C3 122.7(3)
C6 C5 C4 120.5(3)
C5 C6 C7 120.7(3)
C6 C7 C8 120.1(3)
C7 C8 C9 119.7(3)
C8 C9 C4 121.0(3)
C11 C10 C1 122.4(3)
C10 C11 C12 127.1(3)
C17 C12 C13 118.3(3)
C17 C12 C11 122.8(3)
C13 C12 C11 118.9(3)
C14 C13 C12 120.9(3)
C15 C14 C13 120.0(3)
C14 C15 C16 120.3(3)
C17 C16 C15 119.9(4)
C16 C17 C12 120.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 F3 1.364(4)
B1 F1 1.372(4)
B1 F2 1.381(4)
B1 O1 1.533(4)
O1 C1 1.279(4)
C1 C2 1.439(4)
C1 C10 1.441(4)
C2 C3 1.343(4)
C2S Cl1 1.707(5)
C2S Cl1S 1.740(5)
C3 C4 1.449(4)
C4 C9 1.392(5)
C4 C5 1.399(4)
C5 C6 1.373(4)
C6 C7 1.373(5)
C7 C8 1.379(5)
C8 C9 1.384(5)
C10 C11 1.336(4)
C11 C12 1.454(4)
C12 C17 1.393(5)
C12 C13 1.395(4)
C13 C14 1.383(5)
C14 C15 1.368(5)
C15 C16 1.388(5)
C16 C17 1.382(5)
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
F3 B1 O1 C1 179.3(3)
F1 B1 O1 C1 -60.7(4)
F2 B1 O1 C1 60.3(4)
B1 O1 C1 C2 0.2(4)
B1 O1 C1 C10 -179.5(3)
O1 C1 C2 C3 -170.3(3)
C10 C1 C2 C3 9.5(5)
C1 C2 C3 C4 175.6(3)
C2 C3 C4 C9 -168.0(3)
C2 C3 C4 C5 11.4(5)
C9 C4 C5 C6 0.0(5)
C3 C4 C5 C6 -179.4(3)
C4 C5 C6 C7 0.5(5)
C5 C6 C7 C8 -0.3(6)
C6 C7 C8 C9 -0.2(6)
C7 C8 C9 C4 0.7(6)
C5 C4 C9 C8 -0.6(5)
C3 C4 C9 C8 178.8(3)
O1 C1 C10 C11 2.7(4)
C2 C1 C10 C11 -177.1(3)
C1 C10 C11 C12 -176.4(3)
C10 C11 C12 C17 6.0(5)
C10 C11 C12 C13 -175.2(3)
C17 C12 C13 C14 0.0(5)
C11 C12 C13 C14 -178.8(3)
C12 C13 C14 C15 0.1(5)
C13 C14 C15 C16 0.1(5)
C14 C15 C16 C17 -0.5(6)
C15 C16 C17 C12 0.7(6)
C13 C12 C17 C16 -0.5(5)
C11 C12 C17 C16 178.3(3)
