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#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/88/4108830.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_4108830
loop_
_publ_author_name
'Manabu Hatano'
'Toshikatsu Maki'
'Katsuhiko Moriyama'
'Manabu Arinobe'
'Kazuaki Ishihara'
_publ_section_title
;
 Pyridinium 1,1'-Binaphthyl-2,2'-disulfonates as Highly Effective Chiral
 Brønsted Acid-Base Combined Salt Catalysts for Enantioselective
 Mannich-Type Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16858
_journal_page_last               16860
_journal_paper_doi               10.1021/ja806875c
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration (S)
_chemical_formula_sum            'C20 H20 Br N O5'
_chemical_formula_weight         434.28
_chemical_name_common
;
[2-Acetyl-1-(4-bromo-phenyl)-2-hydroxy-3-oxo-butyl]
-carbamic acid benzyl ester
;
_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                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   6.001(5)
_cell_length_b                   10.898(5)
_cell_length_c                   29.128(5)
_cell_measurement_temperature    173(2)
_cell_volume                     1904.9(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            13697
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.189
_exptl_absorpt_correction_T_max  0.6686
_exptl_absorpt_correction_T_min  0.5596
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0312
_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)+(0.0368P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                4218
_reflns_number_total             4714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806875c_si_003.cif
_cod_data_source_block           morib1
_cod_database_code               4108830
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -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 -0.0469(3) 0.23388(16) 0.14470(6) 0.0216(3) Uani 1 1 d .
H1 H -0.151(4) 0.295(2) 0.1531(7) 0.021(5) Uiso 1 1 d .
C2 C -0.1064(3) 0.18383(16) 0.09755(6) 0.0227(4) Uani 1 1 d .
C3 C -0.3044(4) 0.22038(17) 0.07698(7) 0.0273(4) Uani 1 1 d .
H2 H -0.395(4) 0.275(2) 0.0896(9) 0.038(7) Uiso 1 1 d .
C4 C -0.3704(3) 0.1722(2) 0.03497(7) 0.0308(4) Uani 1 1 d .
H3 H -0.511(5) 0.191(2) 0.0216(8) 0.035(6) Uiso 1 1 d .
C5 C -0.2344(3) 0.08740(17) 0.01366(7) 0.0290(4) Uani 1 1 d .
C6 C -0.0329(4) 0.05280(19) 0.03247(7) 0.0340(5) Uani 1 1 d .
H4 H 0.059(5) 0.002(3) 0.0177(10) 0.056(8) Uiso 1 1 d .
C7 C 0.0296(4) 0.10130(19) 0.07484(7) 0.0305(4) Uani 1 1 d .
H5 H 0.165(4) 0.078(2) 0.0881(8) 0.030(5) Uiso 1 1 d .
Br1 Br -0.32516(5) 0.01882(2) -0.043215(7) 0.04908(9) Uani 1 1 d .
N1 N 0.1746(3) 0.28705(14) 0.14599(6) 0.0242(3) Uani 1 1 d .
H6 H 0.283(4) 0.248(2) 0.1432(7) 0.021(6) Uiso 1 1 d .
C8 C 0.2145(3) 0.40263(17) 0.16025(6) 0.0247(4) Uani 1 1 d .
O1 O 0.0746(2) 0.47552(14) 0.17113(6) 0.0434(4) Uani 1 1 d .
O2 O 0.4358(2) 0.42509(12) 0.15961(5) 0.0277(3) Uani 1 1 d .
C9 C 0.5034(4) 0.54807(17) 0.17347(7) 0.0296(4) Uani 1 1 d .
H7 H 0.648(5) 0.534(2) 0.1840(9) 0.046(7) Uiso 1 1 d .
H8 H 0.419(4) 0.572(2) 0.1987(8) 0.033(6) Uiso 1 1 d .
C10 C 0.4915(3) 0.63703(17) 0.13441(7) 0.0279(4) Uani 1 1 d .
C11 C 0.3048(4) 0.70932(18) 0.12737(8) 0.0342(4) Uani 1 1 d .
H9 H 0.181(5) 0.698(2) 0.1461(8) 0.034(6) Uiso 1 1 d .
C12 C 0.2966(5) 0.7921(2) 0.09127(10) 0.0505(7) Uani 1 1 d .
H10 H 0.170(6) 0.841(3) 0.0877(10) 0.055(8) Uiso 1 1 d .
C13 C 0.4737(6) 0.8026(3) 0.06210(12) 0.0628(9) Uani 1 1 d .
H11 H 0.477(6) 0.842(3) 0.0390(11) 0.059(9) Uiso 1 1 d .
C14 C 0.6602(6) 0.7317(3) 0.06830(11) 0.0621(8) Uani 1 1 d .
H12 H 0.776(6) 0.732(3) 0.0517(11) 0.057(8) Uiso 1 1 d .
C15 C 0.6702(5) 0.6489(2) 0.10463(9) 0.0422(5) Uani 1 1 d .
H13 H 0.781(5) 0.604(2) 0.1098(9) 0.038(7) Uiso 1 1 d .
C16 C -0.0602(3) 0.13256(16) 0.18279(6) 0.0227(3) Uani 1 1 d .
O3 O 0.1042(2) 0.04346(13) 0.17601(5) 0.0292(3) Uani 1 1 d .
H14 H 0.196(5) 0.069(3) 0.1874(10) 0.039(8) Uiso 1 1 d .
C17 C -0.0253(3) 0.19732(18) 0.23006(7) 0.0296(4) Uani 1 1 d .
O4 O 0.1423(3) 0.17456(17) 0.25081(6) 0.0471(4) Uani 1 1 d .
C18 C -0.1922(4) 0.2894(2) 0.24628(7) 0.0384(5) Uani 1 1 d .
H15 H -0.1808 0.2983 0.2797 0.058 Uiso 1 1 calc R
H16 H -0.3425 0.2617 0.2382 0.058 Uiso 1 1 calc R
H17 H -0.1627 0.3687 0.2316 0.058 Uiso 1 1 calc R
C19 C -0.2879(3) 0.06939(17) 0.18171(7) 0.0260(4) Uani 1 1 d .
O5 O -0.4530(2) 0.13038(14) 0.17938(7) 0.0437(4) Uani 1 1 d .
C20 C -0.2959(4) -0.0664(2) 0.18385(14) 0.0668(9) Uani 1 1 d .
H18 H -0.4500 -0.0942 0.1798 0.100 Uiso 1 1 calc R
H19 H -0.2402 -0.0941 0.2137 0.100 Uiso 1 1 calc R
H20 H -0.2027 -0.1008 0.1594 0.100 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'
N N 0.0061 0.0033 '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
N1 C1 C2 112.44(15)
N1 C1 C16 108.04(14)
C2 C1 C16 112.01(15)
N1 C1 H1 108.6(13)
C2 C1 H1 109.4(13)
C16 C1 H1 106.1(13)
C7 C2 C3 119.01(19)
C7 C2 C1 121.80(17)
C3 C2 C1 119.18(17)
C2 C3 C4 121.00(19)
C2 C3 H2 122.5(16)
C4 C3 H2 116.5(16)
C5 C4 C3 118.75(19)
C5 C4 H3 119.1(15)
C3 C4 H3 122.0(15)
C4 C5 C6 121.49(19)
C4 C5 Br1 119.13(16)
C6 C5 Br1 119.37(16)
C5 C6 C7 118.9(2)
C5 C6 H4 121.3(19)
C7 C6 H4 119.7(19)
C2 C7 C6 120.8(2)
C2 C7 H5 119.3(14)
C6 C7 H5 119.9(14)
C8 N1 C1 122.96(17)
C8 N1 H6 113.1(16)
C1 N1 H6 123.0(16)
O1 C8 N1 125.19(18)
O1 C8 O2 124.92(18)
N1 C8 O2 109.88(17)
C8 O2 C9 115.88(16)
O2 C9 C10 111.85(16)
O2 C9 H7 101.6(17)
C10 C9 H7 113.5(16)
O2 C9 H8 108.9(15)
C10 C9 H8 113.2(15)
H7 C9 H8 107(2)
C11 C10 C15 118.7(2)
C11 C10 C9 121.31(19)
C15 C10 C9 120.0(2)
C10 C11 C12 120.7(2)
C10 C11 H9 118.8(15)
C12 C11 H9 120.3(16)
C13 C12 C11 120.0(3)
C13 C12 H10 121.0(19)
C11 C12 H10 119.0(19)
C12 C13 C14 120.4(3)
C12 C13 H11 126(3)
C14 C13 H11 113(3)
C13 C14 C15 120.0(3)
C13 C14 H12 126(2)
C15 C14 H12 114(2)
C10 C15 C14 120.2(3)
C10 C15 H13 116.5(18)
C14 C15 H13 123.3(18)
O3 C16 C19 108.34(15)
O3 C16 C17 110.11(15)
C19 C16 C17 109.95(15)
O3 C16 C1 110.69(15)
C19 C16 C1 110.35(14)
C17 C16 C1 107.40(14)
C16 O3 H14 102(2)
O4 C17 C18 122.8(2)
O4 C17 C16 117.6(2)
C18 C17 C16 119.50(17)
C17 C18 H15 109.5
C17 C18 H16 109.5
H15 C18 H16 109.5
C17 C18 H17 109.5
H15 C18 H17 109.5
H16 C18 H17 109.5
O5 C19 C20 122.10(19)
O5 C19 C16 119.41(16)
C20 C19 C16 118.49(17)
C19 C20 H18 109.5
C19 C20 H19 109.5
H18 C20 H19 109.5
C19 C20 H20 109.5
H18 C20 H20 109.5
H19 C20 H20 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.451(3)
C1 C2 1.520(3)
C1 C16 1.567(2)
C1 H1 0.94(2)
C2 C7 1.383(3)
C2 C3 1.389(3)
C3 C4 1.390(3)
C3 H2 0.88(3)
C4 C5 1.380(3)
C4 H3 0.95(3)
C5 C6 1.380(3)
C5 Br1 1.897(2)
C6 C7 1.394(3)
C6 H4 0.89(3)
C7 H5 0.93(3)
N1 C8 1.348(2)
N1 H6 0.78(2)
C8 O1 1.199(2)
C8 O2 1.350(2)
O2 C9 1.457(2)
C9 C10 1.496(3)
C9 H7 0.93(3)
C9 H8 0.93(3)
C10 C11 1.385(3)
C10 C15 1.386(3)
C11 C12 1.386(3)
C11 H9 0.93(3)
C12 C13 1.365(5)
C12 H10 0.93(3)
C13 C14 1.372(5)
C13 H11 0.80(3)
C14 C15 1.392(4)
C14 H12 0.85(3)
C15 H13 0.84(3)
C16 O3 1.398(2)
C16 C19 1.531(3)
C16 C17 1.561(3)
O3 H14 0.70(3)
C17 O4 1.199(3)
C17 C18 1.495(3)
C18 H15 0.9800
C18 H16 0.9800
C18 H17 0.9800
C19 O5 1.195(2)
C19 C20 1.482(3)
C20 H18 0.9800
C20 H19 0.9800
C20 H20 0.9800
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
N1 C1 C2 C7 53.3(2)
C16 C1 C2 C7 -68.6(2)
N1 C1 C2 C3 -127.78(18)
C16 C1 C2 C3 110.32(19)
C7 C2 C3 C4 2.2(3)
C1 C2 C3 C4 -176.76(17)
C2 C3 C4 C5 -0.5(3)
C3 C4 C5 C6 -2.0(3)
C3 C4 C5 Br1 178.94(15)
C4 C5 C6 C7 2.6(3)
Br1 C5 C6 C7 -178.36(16)
C3 C2 C7 C6 -1.6(3)
C1 C2 C7 C6 177.34(18)
C5 C6 C7 C2 -0.7(3)
C2 C1 N1 C8 125.27(19)
C16 C1 N1 C8 -110.60(19)
C1 N1 C8 O1 -3.8(3)
C1 N1 C8 O2 177.37(16)
O1 C8 O2 C9 0.1(3)
N1 C8 O2 C9 178.90(15)
C8 O2 C9 C10 -84.4(2)
O2 C9 C10 C11 94.6(2)
O2 C9 C10 C15 -85.9(2)
C15 C10 C11 C12 0.0(3)
C9 C10 C11 C12 179.5(2)
C10 C11 C12 C13 0.2(4)
C11 C12 C13 C14 0.0(5)
C12 C13 C14 C15 -0.4(5)
C11 C10 C15 C14 -0.3(3)
C9 C10 C15 C14 -179.9(2)
C13 C14 C15 C10 0.5(4)
N1 C1 C16 O3 -57.7(2)
C2 C1 C16 O3 66.66(19)
N1 C1 C16 C19 -177.65(15)
C2 C1 C16 C19 -53.3(2)
N1 C1 C16 C17 62.51(19)
C2 C1 C16 C17 -173.11(15)
O3 C16 C17 O4 8.3(2)
C19 C16 C17 O4 127.6(2)
C1 C16 C17 O4 -112.3(2)
O3 C16 C17 C18 -175.29(17)
C19 C16 C17 C18 -56.0(2)
C1 C16 C17 C18 64.1(2)
O3 C16 C19 O5 -167.96(19)
C17 C16 C19 O5 71.7(2)
C1 C16 C19 O5 -46.6(2)
O3 C16 C19 C20 12.3(3)
C17 C16 C19 C20 -108.0(3)
C1 C16 C19 C20 133.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139117528
