#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:38:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178788 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/42/4104294.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_4104294
loop_
_publ_author_name
'Tim A. Cernak'
'Tristan H. Lambert'
_publ_section_title
;
 Multicatalytic Synthesis of α-Pyrrolidinyl Ketones via a Tandem
 Palladium(II)/Indium(III)-Catalyzed
 Aminochlorocarbonylation/Friedel-Crafts Acylation Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3124
_journal_page_last               3125
_journal_paper_doi               10.1021/ja809897f
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_sum            'C24 H31 N O5 S'
_chemical_formula_weight         445.56
_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                   7.6139(4)
_cell_length_b                   12.7418(7)
_cell_length_c                   24.1476(14)
_cell_measurement_reflns_used    9829
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      32.42
_cell_measurement_theta_min      2.68
_cell_volume                     2342.7(2)
_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      125(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            40239
_diffrn_reflns_theta_full        32.61
_diffrn_reflns_theta_max         32.61
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.9501
_exptl_absorpt_correction_T_min  0.8889
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.38(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         8171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0312
_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)+(0.0571P)²+0.2787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                7848
_reflns_number_total             8171
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja809897f_si_001.cif
_cod_data_source_block           19s10
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4104294
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
S S 0.15413(3) 0.957926(19) 0.837364(9) 0.02054(5) Uani 1 1 d .
O1 O 0.13338(11) 1.05244(7) 0.86925(3) 0.02988(16) Uani 1 1 d .
O2 O 0.05274(10) 0.86655(6) 0.85197(3) 0.02721(15) Uani 1 1 d .
O3 O 0.43344(15) 0.61240(7) 0.79646(3) 0.03441(19) Uani 1 1 d .
O4 O 0.58023(12) 0.64704(6) 0.95899(3) 0.02856(16) Uani 1 1 d .
O5 O 0.47186(15) 0.27526(6) 0.98277(3) 0.0367(2) Uani 1 1 d .
N N 0.35993(10) 0.92411(6) 0.84120(3) 0.01892(13) Uani 1 1 d .
C1 C 0.10796(12) 0.98931(8) 0.76761(4) 0.02260(17) Uani 1 1 d .
C2 C 0.07896(15) 0.90931(9) 0.72941(4) 0.0293(2) Uani 1 1 d .
H2B H 0.0781 0.8381 0.7410 0.035 Uiso 1 1 calc R
C3 C 0.05130(18) 0.93480(11) 0.67415(5) 0.0369(3) Uani 1 1 d .
H3A H 0.0335 0.8803 0.6479 0.044 Uiso 1 1 calc R
C4 C 0.04919(15) 1.03944(12) 0.65654(5) 0.0379(3) Uani 1 1 d .
C5 C 0.07552(16) 1.11757(11) 0.69523(6) 0.0375(3) Uani 1 1 d .
H5A H 0.0727 1.1889 0.6838 0.045 Uiso 1 1 calc R
C6 C 0.10625(15) 1.09378(9) 0.75076(5) 0.0303(2) Uani 1 1 d .
H6A H 0.1258 1.1484 0.7768 0.036 Uiso 1 1 calc R
C7 C 0.0168(2) 1.06543(17) 0.59621(6) 0.0554(5) Uani 1 1 d .
H7A H 0.0202 1.1417 0.5911 0.083 Uiso 1 1 calc R
H7B H -0.0987 1.0388 0.5851 0.083 Uiso 1 1 calc R
H7C H 0.1079 1.0326 0.5734 0.083 Uiso 1 1 calc R
C8 C 0.49546(12) 1.00500(8) 0.82596(4) 0.02136(16) Uani 1 1 d .
H8A H 0.4455 1.0507 0.7962 0.026 Uiso 1 1 calc R
C9 C 0.64343(13) 0.93883(8) 0.80065(4) 0.02378(17) Uani 1 1 d .
H9A H 0.7078 0.9790 0.7720 0.029 Uiso 1 1 calc R
H9B H 0.7274 0.9157 0.8295 0.029 Uiso 1 1 calc R
C10 C 0.54839(14) 0.84518(8) 0.77519(4) 0.02431(17) Uani 1 1 d .
H10A H 0.6294 0.7852 0.7701 0.029 Uiso 1 1 calc R
H10B H 0.4964 0.8638 0.7389 0.029 Uiso 1 1 calc R
C11 C 0.40555(12) 0.81921(7) 0.81744(4) 0.01941(15) Uani 1 1 d .
H11A H 0.3010 0.7889 0.7982 0.023 Uiso 1 1 calc R
C12 C 0.54873(14) 1.07495(9) 0.87469(5) 0.02751(19) Uani 1 1 d .
H12A H 0.4412 1.1129 0.8875 0.033 Uiso 1 1 calc R
C13 C 0.68006(15) 1.15737(10) 0.85428(6) 0.0360(2) Uani 1 1 d .
H13A H 0.6299 1.1952 0.8227 0.054 Uiso 1 1 calc R
H13B H 0.7890 1.1226 0.8429 0.054 Uiso 1 1 calc R
H13C H 0.7053 1.2070 0.8842 0.054 Uiso 1 1 calc R
C14 C 0.6221(2) 1.01406(11) 0.92415(5) 0.0377(3) Uani 1 1 d .
H14A H 0.5355 0.9622 0.9365 0.056 Uiso 1 1 calc R
H14B H 0.6474 1.0629 0.9545 0.056 Uiso 1 1 calc R
H14C H 0.7304 0.9781 0.9132 0.056 Uiso 1 1 calc R
C15 C 0.46434(13) 0.74589(7) 0.86405(4) 0.02093(16) Uani 1 1 d .
H15A H 0.5861 0.7634 0.8751 0.025 Uiso 1 1 calc R
H15B H 0.3875 0.7560 0.8967 0.025 Uiso 1 1 calc R
C16 C 0.45593(13) 0.63247(7) 0.84553(4) 0.02195(16) Uani 1 1 d .
C17 C 0.46461(13) 0.54504(7) 0.88608(3) 0.02037(15) Uani 1 1 d .
C18 C 0.52423(13) 0.55141(7) 0.94123(4) 0.02127(16) Uani 1 1 d .
C19 C 0.52866(14) 0.46216(8) 0.97506(4) 0.02397(17) Uani 1 1 d .
H19A H 0.5707 0.4668 1.0120 0.029 Uiso 1 1 calc R
C20 C 0.47072(16) 0.36659(8) 0.95391(4) 0.02625(19) Uani 1 1 d .
C21 C 0.40596(17) 0.35900(8) 0.89985(4) 0.0288(2) Uani 1 1 d .
H21A H 0.3631 0.2941 0.8860 0.035 Uiso 1 1 calc R
C22 C 0.40546(14) 0.44720(8) 0.86705(4) 0.02391(17) Uani 1 1 d .
H22A H 0.3635 0.4417 0.8301 0.029 Uiso 1 1 calc R
C23 C 0.6332(2) 0.65787(10) 1.01539(5) 0.0430(3) Uani 1 1 d .
H23A H 0.6699 0.7304 1.0223 0.064 Uiso 1 1 calc R
H23B H 0.7315 0.6103 1.0229 0.064 Uiso 1 1 calc R
H23C H 0.5344 0.6403 1.0397 0.064 Uiso 1 1 calc R
C24 C 0.5424(2) 0.27697(10) 1.03750(5) 0.0380(3) Uani 1 1 d .
H24A H 0.5347 0.2066 1.0537 0.057 Uiso 1 1 calc R
H24B H 0.4754 0.3265 1.0603 0.057 Uiso 1 1 calc R
H24C H 0.6657 0.2990 1.0361 0.057 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'
S S 0.1246 0.1234 '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
O1 S O2 119.13(5)
O1 S N 107.28(5)
O2 S N 106.73(4)
O1 S C1 107.40(5)
O2 S C1 108.04(5)
N S C1 107.81(4)
C18 O4 C23 118.43(8)
C20 O5 C24 117.72(9)
C11 N C8 111.05(7)
C11 N S 116.00(6)
C8 N S 117.71(6)
C6 C1 C2 120.34(10)
C6 C1 S 119.80(8)
C2 C1 S 119.83(8)
C3 C2 C1 119.28(11)
C2 C3 C4 121.08(12)
C5 C4 C3 118.69(10)
C5 C4 C7 121.14(14)
C3 C4 C7 120.17(14)
C4 C5 C6 121.23(12)
C1 C6 C5 119.36(12)
N C8 C12 113.11(8)
N C8 C9 102.98(7)
C12 C8 C9 115.57(8)
C10 C9 C8 104.01(8)
C9 C10 C11 103.77(8)
N C11 C10 103.19(7)
N C11 C15 109.36(7)
C10 C11 C15 114.55(8)
C14 C12 C8 113.68(9)
C14 C12 C13 111.13(10)
C8 C12 C13 108.95(10)
C16 C15 C11 110.68(7)
O3 C16 C17 119.20(9)
O3 C16 C15 119.42(8)
C17 C16 C15 121.29(7)
C22 C17 C18 117.65(8)
C22 C17 C16 115.88(8)
C18 C17 C16 126.47(9)
O4 C18 C19 122.40(8)
O4 C18 C17 116.77(8)
C19 C18 C17 120.81(9)
C20 C19 C18 119.24(9)
O5 C20 C19 124.04(9)
O5 C20 C21 114.99(9)
C19 C20 C21 120.97(9)
C22 C21 C20 118.82(10)
C21 C22 C17 122.47(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S O1 1.4380(8)
S O2 1.4408(8)
S N 1.6278(8)
S C1 1.7666(10)
O3 C16 1.2242(12)
O4 C18 1.3604(12)
O4 C23 1.4269(13)
O5 C20 1.3564(12)
O5 C24 1.4269(15)
N C11 1.4954(12)
N C8 1.5043(12)
C1 C6 1.3920(14)
C1 C2 1.3923(16)
C2 C3 1.3896(15)
C3 C4 1.3994(19)
C4 C5 1.380(2)
C4 C7 1.5141(17)
C5 C6 1.3947(17)
C8 C12 1.5310(15)
C8 C9 1.5342(14)
C9 C10 1.5250(15)
C10 C11 1.5275(13)
C11 C15 1.5298(12)
C12 C14 1.5298(17)
C12 C13 1.5316(16)
C15 C16 1.5142(13)
C16 C17 1.4846(13)
C17 C22 1.4029(13)
C17 C18 1.4094(12)
C18 C19 1.4007(13)
C19 C20 1.3922(14)
C20 C21 1.3989(15)
C21 C22 1.3748(14)
