#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/48/1504848.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_1504848
loop_
_publ_author_name
'He, Ming'
'Beahm, Brendan J.'
'Bode, Jeffrey W.'
_publ_section_title
;
 Chiral NHC-catalyzed oxodiene Diels-Alder reactions with
 alpha-chloroaldehyde bisulfite salts.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3817
_journal_page_last               3820
_journal_paper_doi               10.1021/ol801502h
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H19 Br O4'
_chemical_formula_weight         415.27
_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                   5.5454(17)
_cell_length_b                   18.341(5)
_cell_length_c                   18.463(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1877.8(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega scan'
_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  0.2305
_diffrn_reflns_av_sigmaI/netI    0.3782
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13895
_diffrn_reflns_theta_full        26.47
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    2.212
_exptl_absorpt_correction_T_max  0.317
_exptl_absorpt_correction_T_min  0.178
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'psi scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.669
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.669
_refine_ls_R_factor_all          0.2831
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.100
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                878
_reflns_number_total             3669
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801502h_si_004.cif
_cod_data_source_block
(3S,4S)-Ethyl_3-benzyl-6-(4-bromophenyl)-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate
_cod_original_cell_volume        1877.9(9)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1504848
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
Br Br 0.7482(3) 0.24412(7) 0.32582(5) 0.0970(5) Uani 1 1 d .
C1 C 0.681(2) 0.3014(6) 0.4065(5) 0.062(4) Uani 1 1 d .
C2 C 0.8337(18) 0.3064(5) 0.4636(5) 0.051(3) Uani 1 1 d .
H2 H 0.9800 0.2817 0.4615 0.061 Uiso 1 1 calc R
C3 C 0.780(2) 0.3472(5) 0.5252(5) 0.048(3) Uani 1 1 d .
H3 H 0.8855 0.3481 0.5644 0.058 Uiso 1 1 calc R
C4 C 0.568(2) 0.3862(5) 0.5267(6) 0.037(3) Uani 1 1 d .
C5 C 0.4134(19) 0.3833(6) 0.4669(7) 0.055(3) Uani 1 1 d .
H5 H 0.2726 0.4109 0.4674 0.066 Uiso 1 1 calc R
C6 C 0.462(2) 0.3424(6) 0.4090(6) 0.055(3) Uani 1 1 d .
H6 H 0.3541 0.3405 0.3705 0.065 Uiso 1 1 calc R
C7 C 0.507(2) 0.4315(6) 0.5891(5) 0.044(3) Uani 1 1 d .
C8 C 0.652(2) 0.4504(6) 0.7110(7) 0.056(4) Uani 1 1 d .
C9 C 0.398(2) 0.4772(5) 0.7282(5) 0.043(3) Uani 1 1 d .
H9 H 0.296(15) 0.434(4) 0.733(4) 0.051 Uiso 1 1 calc .
C10 C 0.3009(19) 0.5211(5) 0.6654(5) 0.042(3) Uani 1 1 d .
H10 H 0.130(15) 0.532(4) 0.674(4) 0.051 Uiso 1 1 calc .
C11 C 0.327(2) 0.4782(5) 0.5977(5) 0.046(3) Uani 1 1 d .
H11 H 0.2154 0.4842 0.5606 0.055 Uiso 1 1 calc R
C12 C 0.3902(19) 0.5169(5) 0.8009(5) 0.054(3) Uani 1 1 d .
H12A H 0.5151 0.5540 0.8010 0.065 Uiso 1 1 calc R
H12B H 0.2363 0.5417 0.8049 0.065 Uiso 1 1 calc R
C13 C 0.423(2) 0.4692(6) 0.8675(5) 0.044(3) Uani 1 1 d .
C14 C 0.261(2) 0.4180(6) 0.8866(6) 0.062(3) Uani 1 1 d .
H14 H 0.1272 0.4106 0.8570 0.075 Uiso 1 1 calc R
C15 C 0.284(2) 0.3768(6) 0.9474(6) 0.068(3) Uani 1 1 d .
H15 H 0.1638 0.3437 0.9597 0.082 Uiso 1 1 calc R
C16 C 0.478(3) 0.3838(7) 0.9895(6) 0.074(4) Uani 1 1 d .
H16 H 0.5024 0.3532 1.0290 0.089 Uiso 1 1 calc R
C17 C 0.641(2) 0.4375(7) 0.9727(7) 0.064(4) Uani 1 1 d .
H17 H 0.7691 0.4466 1.0040 0.077 Uiso 1 1 calc R
C18 C 0.618(2) 0.4772(6) 0.9116(7) 0.061(4) Uani 1 1 d .
H18 H 0.7378 0.5106 0.8995 0.073 Uiso 1 1 calc R
C19 C 0.441(3) 0.5913(6) 0.6575(6) 0.052(3) Uani 1 1 d .
C20 C 0.409(2) 0.7204(6) 0.6466(7) 0.091(5) Uani 1 1 d .
H20A H 0.5489 0.7246 0.6778 0.110 Uiso 1 1 calc R
H20B H 0.4621 0.7257 0.5968 0.110 Uiso 1 1 calc R
C21 C 0.243(3) 0.7759(6) 0.6633(7) 0.136(6) Uani 1 1 d .
H21A H 0.0840 0.7608 0.6493 0.205 Uiso 1 1 calc R
H21B H 0.2856 0.8195 0.6376 0.205 Uiso 1 1 calc R
H21C H 0.2463 0.7852 0.7145 0.205 Uiso 1 1 calc R
O1 O 0.6874(12) 0.4231(3) 0.6438(4) 0.053(2) Uani 1 1 d .
O2 O 0.8159(14) 0.4492(4) 0.7518(4) 0.065(2) Uani 1 1 d .
O3 O 0.6516(15) 0.5955(4) 0.6526(5) 0.093(3) Uani 1 1 d .
O4 O 0.2980(13) 0.6488(4) 0.6564(3) 0.065(2) 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'
Br Br -0.2901 2.4595 '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 118.2(9)
C2 C1 Br 122.3(10)
C6 C1 Br 119.6(10)
C1 C2 C3 122.5(10)
C1 C2 H2 118.8
C3 C2 H2 118.8
C4 C3 C2 118.5(10)
C4 C3 H3 120.7
C2 C3 H3 120.7
C3 C4 C5 119.1(9)
C3 C4 C7 120.6(11)
C5 C4 C7 120.2(10)
C6 C5 C4 122.1(11)
C6 C5 H5 119.0
C4 C5 H5 119.0
C5 C6 C1 119.6(11)
C5 C6 H6 120.2
C1 C6 H6 120.2
C11 C7 O1 120.8(9)
C11 C7 C4 129.6(10)
O1 C7 C4 109.4(10)
O2 C8 O1 117.8(11)
O2 C8 C9 125.8(11)
O1 C8 C9 116.4(10)
C10 C9 C8 109.9(9)
C10 C9 C12 114.2(8)
C8 C9 C12 111.3(10)
C10 C9 H9 107(5)
C8 C9 H9 107(5)
C12 C9 H9 107(4)
C11 C10 C19 108.7(9)
C11 C10 C9 109.2(8)
C19 C10 C9 110.1(8)
C11 C10 H10 110(5)
C19 C10 H10 109(5)
C9 C10 H10 110(5)
C7 C11 C10 121.2(10)
C7 C11 H11 119.4
C10 C11 H11 119.4
C13 C12 C9 115.6(8)
C13 C12 H12A 108.4
C9 C12 H12A 108.4
C13 C12 H12B 108.4
C9 C12 H12B 108.4
H12A C12 H12B 107.4
C14 C13 C18 116.7(11)
C14 C13 C12 122.1(11)
C18 C13 C12 121.2(11)
C13 C14 C15 122.7(12)
C13 C14 H14 118.7
C15 C14 H14 118.7
C16 C15 C14 120.2(13)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C17 118.1(12)
C15 C16 H16 121.0
C17 C16 H16 121.0
C18 C17 C16 121.0(12)
C18 C17 H17 119.5
C16 C17 H17 119.5
C17 C18 C13 121.1(12)
C17 C18 H18 119.4
C13 C18 H18 119.4
O3 C19 O4 123.0(11)
O3 C19 C10 125.1(11)
O4 C19 C10 112.0(11)
C21 C20 O4 110.3(10)
C21 C20 H20A 109.6
O4 C20 H20A 109.6
C21 C20 H20B 109.6
O4 C20 H20B 109.6
H20A C20 H20B 108.1
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C8 O1 C7 120.4(9)
C19 O4 C20 117.8(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C1 1.861(10)
C1 C2 1.356(13)
C1 C6 1.427(14)
C2 C3 1.393(12)
C2 H2 0.9300
C3 C4 1.379(13)
C3 H3 0.9300
C4 C5 1.399(12)
C4 C7 1.460(13)
C5 C6 1.334(13)
C5 H5 0.9300
C6 H6 0.9300
C7 C11 1.322(12)
C7 O1 1.431(11)
C8 O2 1.180(11)
C8 O1 1.353(12)
C8 C9 1.525(14)
C9 C10 1.512(12)
C9 C12 1.527(12)
C9 H9 0.97(7)
C10 C11 1.484(12)
C10 C19 1.511(14)
C10 H10 0.98(8)
C11 H11 0.9300
C12 C13 1.520(12)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.350(13)
C13 C18 1.362(13)
C14 C15 1.359(12)
C14 H14 0.9300
C15 C16 1.335(15)
C15 H15 0.9300
C16 C17 1.371(14)
C16 H16 0.9300
C17 C18 1.349(13)
C17 H17 0.9300
C18 H18 0.9300
C19 O3 1.174(11)
C19 O4 1.319(11)
C20 C21 1.405(15)
C20 O4 1.461(11)
C20 H20A 0.9700
C20 H20B 0.9700
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
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 3.0(16)
Br C1 C2 C3 -177.7(8)
C1 C2 C3 C4 -2.7(15)
C2 C3 C4 C5 0.2(14)
C2 C3 C4 C7 -178.2(9)
C3 C4 C5 C6 2.0(16)
C7 C4 C5 C6 -179.6(10)
C4 C5 C6 C1 -1.7(17)
C2 C1 C6 C5 -0.7(16)
Br C1 C6 C5 179.9(8)
C3 C4 C7 C11 172.2(10)
C5 C4 C7 C11 -6.2(16)
C3 C4 C7 O1 -3.6(12)
C5 C4 C7 O1 178.0(8)
O2 C8 C9 C10 139.0(12)
O1 C8 C9 C10 -43.9(12)
O2 C8 C9 C12 11.4(16)
O1 C8 C9 C12 -171.5(8)
C8 C9 C10 C11 51.8(11)
C12 C9 C10 C11 177.7(9)
C8 C9 C10 C19 -67.5(11)
C12 C9 C10 C19 58.4(12)
O1 C7 C11 C10 -2.6(15)
C4 C7 C11 C10 -178.0(9)
C19 C10 C11 C7 89.1(12)
C9 C10 C11 C7 -31.1(13)
C10 C9 C12 C13 164.7(9)
C8 C9 C12 C13 -70.1(12)
C9 C12 C13 C14 -65.9(14)
C9 C12 C13 C18 115.4(11)
C18 C13 C14 C15 1.3(16)
C12 C13 C14 C15 -177.5(10)
C13 C14 C15 C16 -2.9(18)
C14 C15 C16 C17 5.3(18)
C15 C16 C17 C18 -6.4(18)
C16 C17 C18 C13 5.0(18)
C14 C13 C18 C17 -2.3(16)
C12 C13 C18 C17 176.5(10)
C11 C10 C19 O3 -66.2(15)
C9 C10 C19 O3 53.4(15)
C11 C10 C19 O4 113.5(9)
C9 C10 C19 O4 -126.9(9)
O2 C8 O1 C7 -172.0(9)
C9 C8 O1 C7 10.7(13)
C11 C7 O1 C8 14.2(14)
C4 C7 O1 C8 -169.6(8)
O3 C19 O4 C20 1.8(16)
C10 C19 O4 C20 -178.0(9)
C21 C20 O4 C19 -166.4(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651487
