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#$Date: 2016-03-21 19:17:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178843 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/97/4109752.cif $
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#
# 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_4109752
loop_
_publ_author_name
'Joshua N. Payette'
'Hisashi Yamamoto'
_publ_section_title
;
 Regioselective and Asymmetric Diels-Alder Reaction of 1- and
 2-Substituted Cyclopentadienes Catalyzed by a Brønsted Acid Activated
 Chiral Oxazaborolidine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9536
_journal_page_last               9537
_journal_paper_doi               10.1021/ja0735958
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C20 H19 Br O2'
_chemical_formula_weight         371.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_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            4
_cell_length_a                   6.446(2)
_cell_length_b                   9.071(3)
_cell_length_c                   29.058(9)
_cell_measurement_temperature    100(2)
_cell_volume                     1699.1(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0901
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            19848
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    2.426
_exptl_absorpt_correction_T_max  0.8296
_exptl_absorpt_correction_T_min  0.5106
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0444
_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)+(0.0378P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                2997
_reflns_number_total             4096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0735958si20070523_111408.cif
_cod_data_source_block           josh05
_cod_database_code               4109752
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
Br1 Br 0.93566(6) 1.25196(4) -0.077110(10) 0.04303(12) Uani 1 1 d .
C1 C 0.8930(5) 1.1031(3) -0.03199(10) 0.0280(8) Uani 1 1 d .
C2 C 0.7075(6) 1.0284(4) -0.02961(10) 0.0318(8) Uani 1 1 d .
H2 H 0.5984 1.0506 -0.0505 0.038 Uiso 1 1 calc R
C3 C 0.6819(5) 0.9201(4) 0.00365(10) 0.0284(7) Uani 1 1 d .
H3 H 0.5539 0.8685 0.0054 0.034 Uiso 1 1 calc R
C4 C 0.8395(5) 0.8857(3) 0.03436(10) 0.0230(7) Uani 1 1 d .
C5 C 1.0252(5) 0.9637(4) 0.03065(10) 0.0283(7) Uani 1 1 d .
H5 H 1.1354 0.9416 0.0512 0.034 Uiso 1 1 calc R
C6 C 1.0533(6) 1.0716(4) -0.00194(10) 0.0312(7) Uani 1 1 d .
H6 H 1.1809 1.1236 -0.0038 0.037 Uiso 1 1 calc R
C7 C 0.8147(5) 0.7665(3) 0.07006(9) 0.0243(6) Uani 1 1 d .
H7A H 0.9529 0.7239 0.0767 0.029 Uiso 1 1 calc R
H7B H 0.7274 0.6870 0.0570 0.029 Uiso 1 1 calc R
C8 C 0.7183(4) 0.8181(3) 0.11498(10) 0.0204(6) Uani 1 1 d .
C9 C 0.4845(4) 0.8570(4) 0.11451(10) 0.0253(7) Uani 1 1 d .
H9A H 0.4509 0.9374 0.0927 0.030 Uiso 1 1 calc R
H9B H 0.3952 0.7703 0.1085 0.030 Uiso 1 1 calc R
C10 C 0.4777(5) 0.9072(4) 0.16497(10) 0.0273(7) Uani 1 1 d .
H10 H 0.3431 0.9497 0.1758 0.033 Uiso 1 1 calc R
C11 C 0.6628(5) 1.0106(3) 0.16576(11) 0.0279(7) Uani 1 1 d .
H11 H 0.6753 1.0975 0.1838 0.034 Uiso 1 1 calc R
C12 C 0.8046(5) 0.9584(3) 0.13672(10) 0.0251(7) Uani 1 1 d .
H12 H 0.9364 1.0009 0.1306 0.030 Uiso 1 1 calc R
C13 C 0.5473(4) 0.7601(4) 0.18854(9) 0.0223(6) Uani 1 1 d .
H13 H 0.4276 0.6902 0.1870 0.027 Uiso 1 1 calc R
C14 C 0.7204(4) 0.6997(3) 0.15568(10) 0.0190(6) Uani 1 1 d .
C15 C 0.6650(5) 0.5432(3) 0.13926(10) 0.0253(7) Uani 1 1 d .
H15A H 0.7750 0.5062 0.1191 0.038 Uiso 1 1 calc R
H15B H 0.5336 0.5459 0.1223 0.038 Uiso 1 1 calc R
H15C H 0.6510 0.4779 0.1660 0.038 Uiso 1 1 calc R
C16 C 0.9343(5) 0.6928(3) 0.17745(10) 0.0228(6) Uani 1 1 d .
C17 C 0.9640(5) 0.7290(4) 0.22611(10) 0.0285(7) Uani 1 1 d .
H17 H 1.1015 0.7245 0.2378 0.034 Uiso 1 1 calc R
C18 C 0.8137(5) 0.7679(4) 0.25549(9) 0.0260(7) Uani 1 1 d .
C19 C 0.8509(5) 0.7985(4) 0.30538(10) 0.0362(8) Uani 1 1 d .
H19A H 0.9989 0.7876 0.3122 0.054 Uiso 1 1 calc R
H19B H 0.7711 0.7287 0.3241 0.054 Uiso 1 1 calc R
H19C H 0.8068 0.8994 0.3126 0.054 Uiso 1 1 calc R
C20 C 0.5973(5) 0.7835(3) 0.23848(10) 0.0256(7) Uani 1 1 d .
O1 O 1.0820(3) 0.6533(2) 0.15423(7) 0.0288(5) Uani 1 1 d .
O2 O 0.4599(4) 0.8159(3) 0.26538(7) 0.0372(6) 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'
Br Br -0.2901 2.4595 '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
C2 C1 C6 121.0(3)
C2 C1 Br1 120.7(2)
C6 C1 Br1 118.3(2)
C1 C2 C3 119.1(3)
C2 C3 C4 121.4(3)
C3 C4 C5 117.7(3)
C3 C4 C7 121.8(3)
C5 C4 C7 120.5(3)
C6 C5 C4 121.8(3)
C5 C6 C1 119.0(3)
C4 C7 C8 114.4(2)
C7 C8 C12 117.6(3)
C7 C8 C9 117.5(3)
C12 C8 C9 99.7(2)
C7 C8 C14 115.1(2)
C12 C8 C14 104.5(2)
C9 C8 C14 99.7(2)
C10 C9 C8 95.0(2)
C11 C10 C9 100.1(2)
C11 C10 C13 107.1(2)
C9 C10 C13 99.0(2)
C12 C11 C10 108.1(3)
C11 C12 C8 108.0(3)
C20 C13 C10 111.3(3)
C20 C13 C14 119.0(2)
C10 C13 C14 103.6(2)
C16 C14 C15 107.6(2)
C16 C14 C13 114.0(2)
C15 C14 C13 110.2(2)
C16 C14 C8 110.1(2)
C15 C14 C8 112.9(2)
C13 C14 C8 102.1(2)
O1 C16 C17 119.8(3)
O1 C16 C14 119.4(3)
C17 C16 C14 120.8(3)
C18 C17 C16 125.5(3)
C17 C18 C20 119.5(3)
C17 C18 C19 123.5(3)
C20 C18 C19 117.0(3)
O2 C20 C18 119.5(3)
O2 C20 C13 119.9(3)
C18 C20 C13 120.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.902(3)
C1 C2 1.376(5)
C1 C6 1.383(5)
C2 C3 1.388(4)
C3 C4 1.388(4)
C4 C5 1.395(4)
C4 C7 1.507(4)
C5 C6 1.374(4)
C7 C8 1.520(4)
C8 C12 1.526(4)
C8 C9 1.548(4)
C8 C14 1.598(4)
C9 C10 1.536(4)
C10 C11 1.518(4)
C10 C13 1.566(4)
C11 C12 1.331(4)
C13 C20 1.502(4)
C13 C14 1.567(4)
C14 C16 1.518(4)
C14 C15 1.540(4)
C16 O1 1.221(4)
C16 C17 1.464(4)
C17 C18 1.339(4)
C18 C20 1.487(4)
C18 C19 1.495(4)
C20 O2 1.217(3)
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
C6 C1 C2 C3 0.2(5)
Br1 C1 C2 C3 179.8(2)
C1 C2 C3 C4 -0.2(5)
C2 C3 C4 C5 -0.1(5)
C2 C3 C4 C7 -178.9(3)
C3 C4 C5 C6 0.3(5)
C7 C4 C5 C6 179.1(3)
C4 C5 C6 C1 -0.2(5)
C2 C1 C6 C5 0.0(5)
Br1 C1 C6 C5 -179.6(2)
C3 C4 C7 C8 -87.5(4)
C5 C4 C7 C8 93.7(3)
C4 C7 C8 C12 -47.7(4)
C4 C7 C8 C9 71.4(4)
C4 C7 C8 C14 -171.6(2)
C7 C8 C9 C10 -177.0(3)
C12 C8 C9 C10 -48.8(3)
C14 C8 C9 C10 57.9(3)
C8 C9 C10 C11 49.3(3)
C8 C9 C10 C13 -60.1(2)
C9 C10 C11 C12 -33.0(3)
C13 C10 C11 C12 69.7(3)
C10 C11 C12 C8 0.5(3)
C7 C8 C12 C11 160.0(3)
C9 C8 C12 C11 31.9(3)
C14 C8 C12 C11 -70.9(3)
C11 C10 C13 C20 64.9(3)
C9 C10 C13 C20 168.5(2)
C11 C10 C13 C14 -64.2(3)
C9 C10 C13 C14 39.3(3)
C20 C13 C14 C16 -8.8(4)
C10 C13 C14 C16 115.5(3)
C20 C13 C14 C15 112.3(3)
C10 C13 C14 C15 -123.4(2)
C20 C13 C14 C8 -127.5(3)
C10 C13 C14 C8 -3.3(3)
C7 C8 C14 C16 78.3(3)
C12 C8 C14 C16 -52.3(3)
C9 C8 C14 C16 -155.1(2)
C7 C8 C14 C15 -41.9(3)
C12 C8 C14 C15 -172.5(2)
C9 C8 C14 C15 84.7(3)
C7 C8 C14 C13 -160.2(2)
C12 C8 C14 C13 69.2(3)
C9 C8 C14 C13 -33.6(3)
C15 C14 C16 O1 60.5(3)
C13 C14 C16 O1 -176.9(3)
C8 C14 C16 O1 -62.9(4)
C15 C14 C16 C17 -117.8(3)
C13 C14 C16 C17 4.8(4)
C8 C14 C16 C17 118.8(3)
O1 C16 C17 C18 -177.2(3)
C14 C16 C17 C18 1.1(5)
C16 C17 C18 C20 -2.9(5)
C16 C17 C18 C19 177.7(3)
C17 C18 C20 O2 178.5(3)
C19 C18 C20 O2 -2.0(4)
C17 C18 C20 C13 -1.7(5)
C19 C18 C20 C13 177.8(3)
C10 C13 C20 O2 67.1(3)
C14 C13 C20 O2 -172.5(3)
C10 C13 C20 C18 -112.8(3)
C14 C13 C20 C18 7.6(4)
