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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/81/7108106.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_7108106
loop_
_publ_author_name
'Kohsuke Ohmatsu'
'Ayano Goto'
'Takashi Ooi'
_publ_section_title
;
 Catalytic asymmetric Mannich-type reactions of alpha-cyano alpha-sulfonyl
 carbanions
;
_journal_name_full               Chem.Commun.
_journal_page_first              7913
_journal_paper_doi               10.1039/c2cc32398b
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration S,R
_chemical_formula_sum            'C21 H23 Cl N2 O4 S'
_chemical_formula_weight         434.92
_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                   8.911(4)
_cell_length_b                   9.919(4)
_cell_length_c                   24.452(11)
_cell_measurement_reflns_used    9738
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.43
_cell_volume                     2161.3(16)
_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      153(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15486
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.9704
_exptl_absorpt_correction_T_min  0.9147
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         5319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.2011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                5149
_reflns_number_total             5319
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc32398b.txt
_cod_data_source_block           2125ago
_cod_original_cell_volume        2161.1(16)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7108106
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
C1 C 0.87468(15) 0.25406(13) 0.88339(5) 0.0175(2) Uani 1 1 d .
H1 H 0.8267 0.3063 0.8531 0.021 Uiso 1 1 calc R
C2 C 0.99477(15) 0.16459(13) 0.85790(5) 0.0178(2) Uani 1 1 d .
C3 C 1.11857(15) 0.12286(13) 0.88848(6) 0.0204(3) Uani 1 1 d .
H3 H 1.1266 0.1490 0.9257 0.024 Uiso 1 1 calc R
C4 C 1.23041(16) 0.04350(14) 0.86519(6) 0.0237(3) Uani 1 1 d .
H4 H 1.3139 0.0156 0.8865 0.028 Uiso 1 1 calc R
C5 C 1.21984(17) 0.00510(16) 0.81065(7) 0.0281(3) Uani 1 1 d .
H5 H 1.2951 -0.0507 0.7950 0.034 Uiso 1 1 calc R
C6 C 1.10003(19) 0.04783(16) 0.77907(6) 0.0284(3) Uani 1 1 d .
H6 H 1.0930 0.0227 0.7417 0.034 Uiso 1 1 calc R
C7 C 0.99030(16) 0.12795(14) 0.80282(6) 0.0213(3) Uani 1 1 d .
C8 C 0.74839(14) 0.17100(14) 0.91207(5) 0.0179(2) Uani 1 1 d .
C9 C 0.79572(16) 0.09529(15) 0.96416(6) 0.0228(3) Uani 1 1 d .
H9A H 0.7108 0.0424 0.9779 0.034 Uiso 1 1 calc R
H9B H 0.8269 0.1604 0.9921 0.034 Uiso 1 1 calc R
H9C H 0.8796 0.0348 0.9557 0.034 Uiso 1 1 calc R
C10 C 0.68264(16) 0.07276(14) 0.87368(6) 0.0213(3) Uani 1 1 d .
C11 C 0.55347(16) 0.38896(15) 0.87758(6) 0.0221(3) Uani 1 1 d .
C12 C 0.61969(17) 0.51592(16) 0.87598(7) 0.0277(3) Uani 1 1 d .
H12 H 0.6841 0.5451 0.9046 0.033 Uiso 1 1 calc R
C13 C 0.5895(2) 0.59893(17) 0.83173(7) 0.0352(4) Uani 1 1 d .
H13 H 0.6334 0.6861 0.8298 0.042 Uiso 1 1 calc R
C14 C 0.4953(2) 0.5548(2) 0.79031(7) 0.0369(4) Uani 1 1 d .
H14 H 0.4762 0.6119 0.7599 0.044 Uiso 1 1 calc R
C15 C 0.4289(2) 0.42930(19) 0.79261(7) 0.0368(4) Uani 1 1 d .
H15 H 0.3638 0.4007 0.7641 0.044 Uiso 1 1 calc R
C16 C 0.45759(19) 0.34463(17) 0.83685(6) 0.0297(3) Uani 1 1 d .
H16 H 0.4122 0.2581 0.8390 0.036 Uiso 1 1 calc R
C17 C 0.99444(15) 0.46636(14) 0.90076(6) 0.0207(3) Uani 1 1 d .
C18 C 1.08207(17) 0.68916(14) 0.92776(6) 0.0259(3) Uani 1 1 d .
C19 C 1.23583(18) 0.67525(17) 0.90117(8) 0.0341(4) Uani 1 1 d .
H19A H 1.3004 0.6191 0.9243 0.051 Uiso 1 1 calc R
H19B H 1.2811 0.7647 0.8970 0.051 Uiso 1 1 calc R
H19C H 1.2249 0.6330 0.8651 0.051 Uiso 1 1 calc R
C20 C 0.96970(19) 0.76316(15) 0.89194(8) 0.0324(3) Uani 1 1 d .
H20A H 0.9640 0.7190 0.8561 0.049 Uiso 1 1 calc R
H20B H 1.0019 0.8569 0.8872 0.049 Uiso 1 1 calc R
H20C H 0.8707 0.7613 0.9094 0.049 Uiso 1 1 calc R
C21 C 1.0937(2) 0.75608(17) 0.98368(8) 0.0372(4) Uani 1 1 d .
H21A H 0.9950 0.7557 1.0014 0.056 Uiso 1 1 calc R
H21B H 1.1281 0.8493 0.9793 0.056 Uiso 1 1 calc R
H21C H 1.1654 0.7063 1.0064 0.056 Uiso 1 1 calc R
Cl1 Cl 0.84750(5) 0.18687(4) 0.760321(14) 0.03162(10) Uani 1 1 d .
N1 N 0.93677(13) 0.35094(11) 0.92172(5) 0.0198(2) Uani 1 1 d .
H23 H 0.9370 0.3354 0.9571 0.024 Uiso 1 1 calc R
N2 N 0.62987(16) -0.00803(15) 0.84649(6) 0.0334(3) Uani 1 1 d .
O1 O 1.01223(14) 0.48554(11) 0.85235(4) 0.0315(3) Uani 1 1 d .
O2 O 1.02456(12) 0.55338(10) 0.94155(4) 0.0243(2) Uani 1 1 d .
O3 O 0.64986(12) 0.36505(11) 0.97765(4) 0.0260(2) Uani 1 1 d .
O4 O 0.46674(11) 0.19650(11) 0.94413(4) 0.0258(2) Uani 1 1 d .
S1 S 0.59295(4) 0.28338(3) 0.933605(13) 0.01920(8) 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'
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'
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
N1 C1 C2 112.46(11)
N1 C1 C8 109.51(11)
C2 C1 C8 112.50(11)
C7 C2 C3 117.55(13)
C7 C2 C1 121.77(12)
C3 C2 C1 120.58(12)
C4 C3 C2 120.96(13)
C5 C4 C3 119.93(14)
C6 C5 C4 120.24(14)
C5 C6 C7 119.05(14)
C6 C7 C2 122.21(14)
C6 C7 Cl1 117.18(11)
C2 C7 Cl1 120.58(11)
C10 C8 C9 108.27(12)
C10 C8 C1 110.44(11)
C9 C8 C1 115.61(11)
C10 C8 S1 106.33(9)
C9 C8 S1 105.27(9)
C1 C8 S1 110.41(10)
N2 C10 C8 176.01(16)
C16 C11 C12 121.96(14)
C16 C11 S1 119.64(12)
C12 C11 S1 118.40(12)
C13 C12 C11 118.51(15)
C12 C13 C14 120.03(16)
C15 C14 C13 120.98(16)
C14 C15 C16 119.78(16)
C11 C16 C15 118.73(16)
O1 C17 O2 126.75(13)
O1 C17 N1 123.55(13)
O2 C17 N1 109.70(12)
O2 C18 C20 110.05(12)
O2 C18 C19 109.05(12)
C20 C18 C19 112.99(14)
O2 C18 C21 102.44(12)
C20 C18 C21 110.59(14)
C19 C18 C21 111.20(14)
C17 N1 C1 117.35(11)
C17 O2 C18 118.93(11)
O3 S1 O4 118.56(7)
O3 S1 C11 108.53(8)
O4 S1 C11 109.82(7)
O3 S1 C8 106.71(7)
O4 S1 C8 105.93(7)
C11 S1 C8 106.62(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.4519(17)
C1 C2 1.5236(19)
C1 C8 1.5610(18)
C2 C7 1.3954(19)
C2 C3 1.396(2)
C3 C4 1.392(2)
C4 C5 1.390(2)
C5 C6 1.384(2)
C6 C7 1.387(2)
C7 Cl1 1.7437(15)
C8 C10 1.4744(19)
C8 C9 1.5374(19)
C8 S1 1.8542(15)
C10 N2 1.142(2)
C11 C16 1.384(2)
C11 C12 1.391(2)
C11 S1 1.7599(15)
C12 C13 1.386(2)
C13 C14 1.386(3)
C14 C15 1.380(3)
C15 C16 1.393(2)
C17 O1 1.2095(18)
C17 O2 1.3461(17)
C17 N1 1.3554(18)
C18 O2 1.4798(18)
C18 C20 1.519(2)
C18 C19 1.523(2)
C18 C21 1.524(2)
O3 S1 1.4398(11)
O4 S1 1.4400(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139182664
