#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/35/7103501.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_7103501
loop_
_publ_author_name
'Xu, Junye'
'Fu, Xiao'
'Low, Ruijuan'
'Goh, Yong-Peng'
'Jiang, Zhiyong'
'Tan, Choon-Hong'
_publ_section_title
;
 Tandem conjugate addition-elimination reaction promoted by chiral
 pyrrolidinyl sulfonamide (CPS).
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5526
_journal_page_last               5528
_journal_paper_doi               10.1039/b810905m
_journal_year                    2008
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C26 H41 Br Cl2 N2 O3 S'
_chemical_formula_weight         612.48
_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                   8.1010(7)
_cell_length_b                   12.7221(10)
_cell_length_c                   28.619(2)
_cell_measurement_reflns_used    3322
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      21.22
_cell_measurement_theta_min      2.61
_cell_volume                     2949.5(4)
_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      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0922
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            20732
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    1.675
_exptl_absorpt_correction_T_max  0.9062
_exptl_absorpt_correction_T_min  0.4649
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         6762
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0579
_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)+(0.0751P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1549
_reflns_number_gt                5181
_reflns_number_total             6762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b810905m.txt
_cod_data_source_block           6373
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7103501
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.18182(6) 0.30280(4) 0.247701(18) 0.05269(18) Uani 1 1 d . . .
S1 S 0.42744(12) 0.44765(8) 0.12892(3) 0.0273(2) Uani 1 1 d . . .
O1 O 0.2518(5) 0.7790(3) 0.09208(13) 0.0564(10) Uani 1 1 d . . .
O2 O 0.5102(3) 0.5459(2) 0.12367(11) 0.0342(7) Uani 1 1 d . . .
O3 O 0.5122(4) 0.3638(2) 0.15186(11) 0.0371(7) Uani 1 1 d . . .
N1 N 0.3344(4) 0.6752(3) 0.22282(11) 0.0300(7) Uani 1 1 d . . .
N2 N 0.2628(4) 0.4684(2) 0.15939(11) 0.0262(7) Uani 1 1 d D . .
C1 C 0.2160(6) 0.8372(4) 0.1231(2) 0.0464(12) Uani 1 1 d . . .
C2 C 0.0981(8) 0.9301(4) 0.1205(3) 0.0726(19) Uani 1 1 d . . .
H2A H 0.1385 0.9826 0.0982 0.087 Uiso 1 1 calc R . .
H2B H -0.0119 0.9070 0.1107 0.087 Uiso 1 1 calc R . .
C3 C 0.0918(9) 0.9760(5) 0.1693(3) 0.079(2) Uani 1 1 d . . .
H3A H 0.1255 1.0500 0.1692 0.095 Uiso 1 1 calc R . .
H3B H -0.0196 0.9706 0.1824 0.095 Uiso 1 1 calc R . .
C4 C 0.2114(8) 0.9104(4) 0.1966(2) 0.0604(16) Uani 1 1 d . . .
H4 H 0.2378 0.9231 0.2281 0.073 Uiso 1 1 calc R . .
C5 C 0.2775(5) 0.8312(3) 0.17146(17) 0.0388(10) Uani 1 1 d . . .
C6 C 0.3989(5) 0.7501(3) 0.18665(15) 0.0319(9) Uani 1 1 d . . .
H6A H 0.4966 0.7856 0.1992 0.038 Uiso 1 1 calc R . .
H6B H 0.4340 0.7097 0.1592 0.038 Uiso 1 1 calc R . .
C7 C 0.2998(6) 0.7309(4) 0.26879(15) 0.0410(11) Uani 1 1 d . . .
H7A H 0.3816 0.7862 0.2745 0.049 Uiso 1 1 calc R . .
H7B H 0.1895 0.7625 0.2686 0.049 Uiso 1 1 calc R . .
C8 C 0.3113(7) 0.6466(4) 0.30547(16) 0.0503(13) Uani 1 1 d . . .
H8A H 0.2028 0.6148 0.3110 0.060 Uiso 1 1 calc R . .
H8B H 0.3522 0.6758 0.3350 0.060 Uiso 1 1 calc R . .
C9 C 0.4306(10) 0.5656(5) 0.2866(2) 0.0703(18) Uani 1 1 d . . .
H9A H 0.5314 0.5640 0.3055 0.084 Uiso 1 1 calc R . .
H9B H 0.3804 0.4956 0.2870 0.084 Uiso 1 1 calc R . .
C10 C 0.4689(5) 0.5981(4) 0.23774(16) 0.0395(11) Uani 1 1 d . . .
H10A H 0.4696 0.5367 0.2171 0.047 Uiso 1 1 calc R . .
H10B H 0.5775 0.6319 0.2363 0.047 Uiso 1 1 calc R . .
C11 C 0.1762(5) 0.6196(3) 0.20771(13) 0.0268(8) Uani 1 1 d . . .
H11A H 0.0862 0.6709 0.2091 0.032 Uiso 1 1 calc R . .
H11B H 0.1520 0.5651 0.2310 0.032 Uiso 1 1 calc R . .
C12 C 0.1712(4) 0.5676(3) 0.15915(13) 0.0241(7) Uani 1 1 d . . .
H12 H 0.2239 0.6157 0.1364 0.029 Uiso 1 1 calc R . .
C13 C -0.0139(4) 0.5521(3) 0.14462(15) 0.0294(9) Uani 1 1 d . . .
C14 C -0.1115(6) 0.4975(4) 0.18351(18) 0.0442(12) Uani 1 1 d . . .
H14A H -0.1217 0.5445 0.2100 0.066 Uiso 1 1 calc R . .
H14B H -0.0540 0.4341 0.1930 0.066 Uiso 1 1 calc R . .
H14C H -0.2205 0.4793 0.1721 0.066 Uiso 1 1 calc R . .
C15 C -0.0195(6) 0.4851(4) 0.10066(19) 0.0511(14) Uani 1 1 d . . .
H15A H 0.0349 0.4184 0.1065 0.077 Uiso 1 1 calc R . .
H15B H 0.0367 0.5215 0.0755 0.077 Uiso 1 1 calc R . .
H15C H -0.1335 0.4726 0.0919 0.077 Uiso 1 1 calc R . .
C16 C -0.0937(5) 0.6575(3) 0.13334(17) 0.0368(10) Uani 1 1 d . . .
H16A H -0.2078 0.6465 0.1243 0.055 Uiso 1 1 calc R . .
H16B H -0.0345 0.6907 0.1078 0.055 Uiso 1 1 calc R . .
H16C H -0.0894 0.7024 0.1607 0.055 Uiso 1 1 calc R . .
C17 C 0.3704(5) 0.4014(3) 0.07195(14) 0.0283(9) Uani 1 1 d . . .
C18 C 0.4082(5) 0.4607(3) 0.03209(14) 0.0330(9) Uani 1 1 d . . .
C19 C 0.3666(6) 0.4160(4) -0.01120(16) 0.0405(11) Uani 1 1 d . . .
H19 H 0.3906 0.4541 -0.0385 0.049 Uiso 1 1 calc R . .
C20 C 0.2931(6) 0.3198(4) -0.01562(16) 0.0417(11) Uani 1 1 d . . .
C21 C 0.2559(6) 0.2650(4) 0.02528(18) 0.0426(11) Uani 1 1 d . . .
H21 H 0.2016 0.1999 0.0228 0.051 Uiso 1 1 calc R . .
C22 C 0.2951(5) 0.3019(3) 0.06876(15) 0.0347(9) Uani 1 1 d . . .
C23 C 0.4833(7) 0.5704(4) 0.03028(19) 0.0532(14) Uani 1 1 d . . .
H23A H 0.4226 0.6168 0.0510 0.080 Uiso 1 1 calc R . .
H23B H 0.4774 0.5972 -0.0014 0.080 Uiso 1 1 calc R . .
H23C H 0.5978 0.5672 0.0401 0.080 Uiso 1 1 calc R . .
C24 C 0.2518(9) 0.2748(5) -0.0628(2) 0.0673(17) Uani 1 1 d . . .
H24A H 0.1370 0.2892 -0.0700 0.101 Uiso 1 1 calc R . .
H24B H 0.2698 0.1994 -0.0624 0.101 Uiso 1 1 calc R . .
H24C H 0.3219 0.3067 -0.0863 0.101 Uiso 1 1 calc R . .
C25 C 0.2516(7) 0.2355(4) 0.10967(17) 0.0453(12) Uani 1 1 d . . .
H25A H 0.1699 0.1837 0.1005 0.068 Uiso 1 1 calc R . .
H25B H 0.2068 0.2795 0.1343 0.068 Uiso 1 1 calc R . .
H25C H 0.3498 0.2000 0.1210 0.068 Uiso 1 1 calc R . .
Cl1A Cl 0.4330(3) 1.00553(19) 0.03286(10) 0.1192(8) Uani 1 1 d D . .
C1S C 0.5486(16) 0.8935(8) 0.0413(3) 0.091(3) Uiso 0.709(8) 1 d PD A 1
H1S1 H 0.6362 0.8890 0.0178 0.110 Uiso 0.709(8) 1 calc PR A 1
H1S2 H 0.4785 0.8310 0.0386 0.110 Uiso 0.709(8) 1 calc PR A 1
Cl1B Cl 0.6345(4) 0.9005(5) 0.09756(16) 0.140(3) Uani 0.709(8) 1 d PD A 1
C2S C 0.520(3) 0.8791(13) 0.0229(7) 0.086(8) Uiso 0.291(8) 1 d PD A 2
H2S1 H 0.4295 0.8285 0.0208 0.104 Uiso 0.291(8) 1 calc PR A 2
H2S2 H 0.5748 0.8805 -0.0076 0.104 Uiso 0.291(8) 1 calc PR A 2
Cl2B Cl 0.6638(11) 0.8304(7) 0.0641(4) 0.107(3) Uiso 0.291(8) 1 d PD A 2
H1N H 0.254(6) 0.420(2) 0.1814(11) 0.032 Uiso 1 1 d 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'
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'
S S 0.1246 0.1234 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 118.50(17) . . ?
O2 S1 N2 107.54(17) . . ?
O3 S1 N2 105.72(18) . . ?
O2 S1 C17 108.23(19) . . ?
O3 S1 C17 107.25(19) . . ?
N2 S1 C17 109.36(18) . . ?
C6 N1 C7 111.4(3) . . ?
C6 N1 C11 113.0(3) . . ?
C7 N1 C11 107.8(3) . . ?
C6 N1 C10 110.6(3) . . ?
C7 N1 C10 100.9(3) . . ?
C11 N1 C10 112.4(3) . . ?
C12 N2 S1 123.9(3) . . ?
O1 C1 C5 125.8(4) . . ?
O1 C1 C2 126.9(5) . . ?
C5 C1 C2 107.3(5) . . ?
C3 C2 C1 106.0(5) . . ?
C4 C3 C2 104.1(5) . . ?
C5 C4 C3 113.3(6) . . ?
C4 C5 C1 109.2(5) . . ?
C4 C5 C6 128.6(5) . . ?
C1 C5 C6 122.2(4) . . ?
C5 C6 N1 114.3(3) . . ?
C8 C7 N1 105.0(4) . . ?
C7 C8 C9 106.0(4) . . ?
C10 C9 C8 106.2(4) . . ?
C9 C10 N1 107.0(4) . . ?
N1 C11 C12 118.5(3) . . ?
N2 C12 C11 110.6(3) . . ?
N2 C12 C13 112.2(3) . . ?
C11 C12 C13 108.6(3) . . ?
C15 C13 C16 107.8(4) . . ?
C15 C13 C14 109.4(4) . . ?
C16 C13 C14 109.5(3) . . ?
C15 C13 C12 108.5(3) . . ?
C16 C13 C12 110.5(3) . . ?
C14 C13 C12 111.0(3) . . ?
C18 C17 C22 121.7(4) . . ?
C18 C17 S1 120.5(3) . . ?
C22 C17 S1 117.7(3) . . ?
C17 C18 C19 116.6(4) . . ?
C17 C18 C23 127.5(4) . . ?
C19 C18 C23 115.9(4) . . ?
C20 C19 C18 123.3(4) . . ?
C19 C20 C21 117.7(4) . . ?
C19 C20 C24 121.4(5) . . ?
C21 C20 C24 120.9(5) . . ?
C22 C21 C20 122.8(4) . . ?
C21 C22 C17 117.9(4) . . ?
C21 C22 C25 117.8(4) . . ?
C17 C22 C25 124.2(4) . . ?
C1S Cl1A C2S 19.7(5) . . ?
Cl1A C1S Cl1B 107.6(5) . . ?
Cl2B C2S Cl1A 118.2(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.427(3) . ?
S1 O3 1.429(3) . ?
S1 N2 1.615(3) . ?
S1 C17 1.794(4) . ?
O1 C1 1.191(6) . ?
N1 C6 1.501(5) . ?
N1 C7 1.521(5) . ?
N1 C11 1.526(5) . ?
N1 C10 1.527(5) . ?
N2 C12 1.464(5) . ?
C1 C5 1.474(7) . ?
C1 C2 1.522(7) . ?
C2 C3 1.515(10) . ?
C3 C4 1.498(9) . ?
C4 C5 1.349(7) . ?
C5 C6 1.490(6) . ?
C7 C8 1.504(7) . ?
C8 C9 1.512(8) . ?
C9 C10 1.490(8) . ?
C11 C12 1.540(5) . ?
C12 C13 1.569(5) . ?
C13 C15 1.520(6) . ?
C13 C16 1.523(5) . ?
C13 C14 1.532(6) . ?
C17 C18 1.401(6) . ?
C17 C22 1.408(6) . ?
C18 C19 1.404(6) . ?
C18 C23 1.524(6) . ?
C19 C20 1.366(7) . ?
C20 C21 1.396(7) . ?
C20 C24 1.504(7) . ?
C21 C22 1.367(6) . ?
C22 C25 1.486(6) . ?
Cl1A C1S 1.722(8) . ?
Cl1A C2S 1.780(10) . ?
C1S Cl1B 1.755(8) . ?
C2S Cl2B 1.766(10) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139180655
