#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/60/1506084.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_1506084
loop_
_publ_author_name
'Garner, Philip'
'Kaniskan, H. Umit'
'Hu, Jieyu'
'Youngs, Wiley J.'
'Panzner, Matthew'
_publ_section_title
;
 Asymmetric multicomponent [C+NC+CC] synthesis of highly functionalized
 pyrrolidines catalyzed by silver(I).
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3647
_journal_page_last               3650
_journal_paper_doi               10.1021/ol061113b
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H34 N2 O5 S'
_chemical_formula_sum            'C25 H34 N2 O5 S'
_chemical_formula_weight         474.60
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 122.954(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.555(3)
_cell_length_b                   7.2399(9)
_cell_length_c                   15.3012(18)
_cell_measurement_reflns_used    3293
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.67
_cell_volume                     2375.5(5)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10682
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.9133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack (1983), 2445 Friedel pairs'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5535
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0636P)²+0.6915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                5025
_reflns_number_total             5535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061113bsi20060505_020505.cif
_cod_data_source_block           mp
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C2   '
_cod_database_code               1506084
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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
S1 S 0.71140(2) 1.23553(7) 0.83493(4) 0.02144(13) Uani 1 1 d .
O1 O 0.68873(7) 0.6146(2) 0.48679(12) 0.0259(4) Uani 1 1 d .
O2 O 0.73840(7) 0.6994(2) 0.65464(11) 0.0278(4) Uani 1 1 d .
O3 O 0.72068(7) 0.7229(2) 0.83892(11) 0.0236(3) Uani 1 1 d .
O4 O 0.68257(9) 1.3130(2) 0.73327(13) 0.0362(4) Uani 1 1 d .
O5 O 0.67360(7) 1.2184(3) 0.87747(13) 0.0345(4) Uani 1 1 d .
N1 N 0.60960(8) 0.7210(3) 0.65392(13) 0.0206(4) Uani 1 1 d .
H1A H 0.6043 0.6379 0.6904 0.025 Uiso 1 1 calc R
N2 N 0.74162(8) 1.0254(2) 0.83774(13) 0.0179(4) Uani 1 1 d .
C1 C 0.64204(10) 0.8976(3) 0.69227(16) 0.0191(4) Uani 1 1 d .
H1 H 0.6154 0.9826 0.7036 0.023 Uiso 1 1 calc R
C2 C 0.58756(9) 0.7079(3) 0.54322(15) 0.0187(4) Uani 1 1 d .
H2 H 0.5469 0.7750 0.5027 0.022 Uiso 1 1 calc R
C3 C 0.63578(9) 0.8187(3) 0.53232(16) 0.0192(4) Uani 1 1 d .
H3 H 0.6168 0.8625 0.4591 0.023 Uiso 1 1 calc R
C4 C 0.64911(10) 0.9807(3) 0.60525(16) 0.0202(4) Uani 1 1 d .
H4A H 0.6188 1.0820 0.5682 0.024 Uiso 1 1 calc R
H4B H 0.6918 1.0289 0.6348 0.024 Uiso 1 1 calc R
C5 C 0.70333(10) 0.8709(3) 0.79490(16) 0.0182(4) Uani 1 1 d .
C6 C 0.80341(9) 1.0030(3) 0.93519(16) 0.0193(4) Uani 1 1 d .
H6 H 0.7990 0.9588 0.9928 0.023 Uiso 1 1 calc R
C7 C 0.83418(9) 1.1947(3) 0.96057(15) 0.0184(4) Uani 1 1 d .
C8 C 0.78452(10) 1.3411(3) 0.92712(18) 0.0251(5) Uani 1 1 d .
H8A H 0.7925 1.4468 0.8949 0.030 Uiso 1 1 calc R
H8B H 0.7844 1.3868 0.9880 0.030 Uiso 1 1 calc R
C9 C 0.88680(10) 1.1844(4) 1.07751(16) 0.0269(5) Uani 1 1 d .
H9A H 0.9054 1.3074 1.1051 0.032 Uiso 1 1 calc R
H9B H 0.8712 1.1336 1.1193 0.032 Uiso 1 1 calc R
C10 C 0.93392(10) 1.0526(4) 1.07707(19) 0.0300(5) Uani 1 1 d .
H10A H 0.9389 0.9383 1.1165 0.036 Uiso 1 1 calc R
H10B H 0.9751 1.1126 1.1079 0.036 Uiso 1 1 calc R
C11 C 0.90482(10) 1.0101(3) 0.96073(18) 0.0248(5) Uani 1 1 d .
H11 H 0.9353 0.9666 0.9434 0.030 Uiso 1 1 calc R
C12 C 0.84940(10) 0.8786(3) 0.92560(18) 0.0256(5) Uani 1 1 d .
H12A H 0.8620 0.7695 0.9718 0.031 Uiso 1 1 calc R
H12B H 0.8311 0.8368 0.8530 0.031 Uiso 1 1 calc R
C13 C 0.87176(10) 1.1939(3) 0.90765(16) 0.0214(4) Uani 1 1 d .
C14 C 0.83354(11) 1.1868(4) 0.78864(17) 0.0273(5) Uani 1 1 d .
H14A H 0.8067 1.2962 0.7608 0.041 Uiso 1 1 calc R
H14B H 0.8076 1.0753 0.7650 0.041 Uiso 1 1 calc R
H14C H 0.8617 1.1843 0.7639 0.041 Uiso 1 1 calc R
C15 C 0.91535(11) 1.3607(4) 0.93943(19) 0.0283(5) Uani 1 1 d .
H15A H 0.9419 1.3463 0.9118 0.042 Uiso 1 1 calc R
H15B H 0.9416 1.3688 1.0156 0.042 Uiso 1 1 calc R
H15C H 0.8905 1.4737 0.9113 0.042 Uiso 1 1 calc R
C16 C 0.57602(10) 0.5099(3) 0.50390(17) 0.0201(4) Uani 1 1 d .
H16A H 0.5523 0.4437 0.5282 0.024 Uiso 1 1 calc R
H16B H 0.6164 0.4460 0.5326 0.024 Uiso 1 1 calc R
C17 C 0.53911(10) 0.5058(3) 0.38395(17) 0.0235(5) Uani 1 1 d .
H17A H 0.4956 0.5446 0.3559 0.028 Uiso 1 1 calc R
H17B H 0.5577 0.5956 0.3596 0.028 Uiso 1 1 calc R
C18 C 0.53872(10) 0.3169(3) 0.34172(15) 0.0214(4) Uani 1 1 d .
C19 C 0.49836(10) 0.1798(3) 0.33298(17) 0.0236(5) Uani 1 1 d .
H19 H 0.4703 0.2045 0.3541 0.028 Uiso 1 1 calc R
C20 C 0.49829(10) 0.0065(3) 0.29375(18) 0.0260(5) Uani 1 1 d .
H20 H 0.4706 -0.0867 0.2888 0.031 Uiso 1 1 calc R
C21 C 0.53879(11) -0.0298(4) 0.26188(17) 0.0257(5) Uani 1 1 d .
H21 H 0.5386 -0.1476 0.2343 0.031 Uiso 1 1 calc R
C22 C 0.57946(11) 0.1056(4) 0.27037(18) 0.0289(5) Uani 1 1 d .
H22 H 0.6072 0.0808 0.2485 0.035 Uiso 1 1 calc R
C23 C 0.57989(11) 0.2769(3) 0.31054(18) 0.0255(5) Uani 1 1 d .
H23 H 0.6084 0.3686 0.3171 0.031 Uiso 1 1 calc R
C24 C 0.69342(9) 0.7072(3) 0.56748(16) 0.0200(4) Uani 1 1 d .
C25 C 0.73967(12) 0.4922(4) 0.5142(2) 0.0370(6) Uani 1 1 d .
H25A H 0.7785 0.5633 0.5459 0.055 Uiso 1 1 calc R
H25B H 0.7321 0.4300 0.4514 0.055 Uiso 1 1 calc R
H25C H 0.7432 0.3999 0.5640 0.055 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
O4 S1 O5 116.99(12)
O4 S1 N2 109.80(10)
O5 S1 N2 108.71(11)
O4 S1 C8 112.99(13)
O5 S1 C8 110.60(11)
N2 S1 C8 95.59(10)
C24 O1 C25 115.05(18)
C1 N1 C2 107.30(17)
C5 N2 C6 118.56(17)
C5 N2 S1 120.98(14)
C6 N2 S1 110.27(13)
N1 C1 C5 110.26(17)
N1 C1 C4 107.37(17)
C5 C1 C4 113.64(17)
N1 C2 C16 112.79(18)
N1 C2 C3 105.16(16)
C16 C2 C3 116.01(17)
C24 C3 C4 111.53(17)
C24 C3 C2 111.44(18)
C4 C3 C2 101.12(17)
C3 C4 C1 104.17(17)
O3 C5 N2 119.79(19)
O3 C5 C1 123.30(19)
N2 C5 C1 116.89(18)
N2 C6 C7 105.93(16)
N2 C6 C12 114.69(17)
C7 C6 C12 103.79(16)
C8 C7 C6 109.12(16)
C8 C7 C9 117.77(18)
C6 C7 C9 104.58(17)
C8 C7 C13 117.86(18)
C6 C7 C13 103.95(17)
C9 C7 C13 101.96(16)
C7 C8 S1 106.94(15)
C10 C9 C7 102.39(18)
C9 C10 C11 103.97(18)
C12 C11 C10 107.50(19)
C12 C11 C13 102.27(17)
C10 C11 C13 102.54(19)
C11 C12 C6 102.04(18)
C14 C13 C15 106.73(18)
C14 C13 C11 114.10(19)
C15 C13 C11 114.58(18)
C14 C13 C7 116.38(17)
C15 C13 C7 112.35(19)
C11 C13 C7 92.58(17)
C2 C16 C17 110.54(17)
C18 C17 C16 112.61(18)
C19 C18 C23 118.4(2)
C19 C18 C17 121.4(2)
C23 C18 C17 120.1(2)
C18 C19 C20 121.0(2)
C21 C20 C19 119.8(2)
C22 C21 C20 119.9(2)
C23 C22 C21 120.1(2)
C22 C23 C18 120.8(2)
O2 C24 O1 123.3(2)
O2 C24 C3 125.8(2)
O1 C24 C3 110.94(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O4 1.4251(18)
S1 O5 1.4338(17)
S1 N2 1.6958(18)
S1 C8 1.788(2)
O1 C24 1.352(3)
O1 C25 1.436(3)
O2 C24 1.198(2)
O3 C5 1.214(3)
N1 C1 1.462(3)
N1 C2 1.469(3)
N2 C5 1.393(3)
N2 C6 1.477(3)
C1 C5 1.510(3)
C1 C4 1.559(3)
C2 C16 1.520(3)
C2 C3 1.553(3)
C3 C24 1.500(3)
C3 C4 1.525(3)
C6 C7 1.537(3)
C6 C12 1.550(3)
C7 C8 1.513(3)
C7 C9 1.548(3)
C7 C13 1.557(3)
C9 C10 1.539(4)
C10 C11 1.542(3)
C11 C12 1.540(3)
C11 C13 1.549(3)
C13 C14 1.529(3)
C13 C15 1.532(3)
C16 C17 1.541(3)
C17 C18 1.510(3)
C18 C19 1.385(3)
C18 C23 1.402(3)
C19 C20 1.391(3)
C20 C21 1.388(3)
C21 C22 1.383(4)
C22 C23 1.381(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21199751 ChemSpider
