#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/56/4025606.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_4025606
loop_
_publ_author_name
'Yongjia Shang'
'Kai Ju'
'Xinwei He'
'Jinsong Hu'
'Shuyan Yu'
'Min Zhang'
'Kaisheng Liao'
'Lifen Wang'
'Ping Zhang'
_publ_section_title
;
 Copper-Catalyzed Multicomponent Reaction: Synthesis of
 4-Arylsulfonylimino-4,5-dihydrofuran Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5743
_journal_page_last               5745
_journal_paper_doi               10.1021/jo1010075
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C20 H18 N O5 S'
_chemical_formula_weight         384.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.1310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0868(8)
_cell_length_b                   15.8235(13)
_cell_length_c                   12.3174(10)
_cell_measurement_reflns_used    6211
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      2.42
_cell_volume                     1941.0(3)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16664
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0501
_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)+(0.0836P)²+0.4669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1668
_reflns_number_gt                3112
_reflns_number_total             4475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1010075_si_001.cif
_cod_data_source_block           071221a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025606
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.23186(6) 0.08240(4) 0.75360(5) 0.0646(2) Uani 1 1 d . . .
O1 O 0.13544(19) 0.02709(14) 0.78756(16) 0.0942(6) Uani 1 1 d . . .
O2 O 0.33221(17) 0.11880(12) 0.83300(13) 0.0820(5) Uani 1 1 d . . .
O3 O 0.22698(17) 0.12958(11) 0.34425(14) 0.0779(5) Uani 1 1 d . . .
O4 O 0.1681(2) 0.02699(12) 0.45167(14) 0.0862(5) Uani 1 1 d . . .
O5 O 0.58625(15) 0.12592(10) 0.57211(12) 0.0630(4) Uani 1 1 d . . .
N1 N 0.30825(19) 0.02435(12) 0.67090(15) 0.0646(5) Uani 1 1 d . . .
C1 C 0.2138(3) 0.24125(18) 0.6726(3) 0.0878(8) Uani 1 1 d . . .
H1 H 0.2969 0.2494 0.7162 0.105 Uiso 1 1 calc R . .
C2 C 0.1568(5) 0.3047(2) 0.6091(4) 0.1245(14) Uani 1 1 d . . .
H2 H 0.1993 0.3568 0.6098 0.149 Uiso 1 1 calc R . .
C3 C 0.0368(6) 0.2920(4) 0.5438(4) 0.1417(19) Uani 1 1 d . . .
H3 H -0.0010 0.3352 0.4978 0.170 Uiso 1 1 calc R . .
C4 C -0.0309(4) 0.2147(4) 0.5447(3) 0.1321(16) Uani 1 1 d . . .
H4 H -0.1140 0.2072 0.5008 0.158 Uiso 1 1 calc R . .
C5 C 0.0265(3) 0.1494(2) 0.6115(2) 0.0922(9) Uani 1 1 d . . .
H5 H -0.0169 0.0978 0.6141 0.111 Uiso 1 1 calc R . .
C6 C 0.1498(2) 0.16391(15) 0.67361(18) 0.0645(6) Uani 1 1 d . . .
C7 C 0.4043(2) 0.06515(12) 0.61528(17) 0.0563(5) Uani 1 1 d . . .
C8 C 0.5340(2) 0.08367(13) 0.65385(17) 0.0572(5) Uani 1 1 d . . .
C9 C 0.6275(2) 0.06891(13) 0.75584(18) 0.0593(5) Uani 1 1 d . . .
C10 C 0.5963(2) 0.01153(15) 0.8337(2) 0.0709(6) Uani 1 1 d . . .
H10 H 0.5149 -0.0172 0.8216 0.085 Uiso 1 1 calc R . .
C11 C 0.6862(3) -0.00283(17) 0.9288(2) 0.0775(7) Uani 1 1 d . . .
H11 H 0.6643 -0.0410 0.9806 0.093 Uiso 1 1 calc R . .
C12 C 0.8074(3) 0.03850(17) 0.9479(2) 0.0766(7) Uani 1 1 d . . .
H12 H 0.8674 0.0284 1.0121 0.092 Uiso 1 1 calc R . .
C13 C 0.8388(3) 0.09453(18) 0.8716(2) 0.0790(7) Uani 1 1 d . . .
H13 H 0.9209 0.1225 0.8839 0.095 Uiso 1 1 calc R . .
C14 C 0.7500(2) 0.11007(17) 0.7763(2) 0.0718(6) Uani 1 1 d . . .
H14 H 0.7728 0.1486 0.7253 0.086 Uiso 1 1 calc R . .
C15 C 0.4886(2) 0.13255(14) 0.48210(18) 0.0617(5) Uani 1 1 d . . .
C16 C 0.5283(3) 0.17516(18) 0.3850(2) 0.0812(7) Uani 1 1 d . . .
H16A H 0.4504 0.1834 0.3303 0.122 Uiso 1 1 calc R . .
H16B H 0.5922 0.1407 0.3553 0.122 Uiso 1 1 calc R . .
H16C H 0.5680 0.2289 0.4067 0.122 Uiso 1 1 calc R . .
C17 C 0.3750(2) 0.09588(13) 0.50388(17) 0.0585(5) Uani 1 1 d . . .
C18 C 0.2465(3) 0.08038(15) 0.43151(19) 0.0660(6) Uani 1 1 d . . .
C19 C 0.1017(3) 0.1148(2) 0.2689(2) 0.0937(9) Uani 1 1 d . . .
H19A H 0.1011 0.0581 0.2391 0.112 Uiso 1 1 calc R . .
H19B H 0.0258 0.1205 0.3078 0.112 Uiso 1 1 calc R . .
C20 C 0.0915(4) 0.1763(2) 0.1803(3) 0.1219(13) Uani 1 1 d . . .
H20A H 0.0902 0.2323 0.2102 0.183 Uiso 1 1 calc R . .
H20B H 0.0102 0.1667 0.1296 0.183 Uiso 1 1 calc R . .
H20C H 0.1672 0.1706 0.1425 0.183 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.73(12) . . ?
O2 S1 N1 107.49(10) . . ?
O1 S1 N1 104.33(12) . . ?
O2 S1 C6 108.19(12) . . ?
O1 S1 C6 109.60(12) . . ?
N1 S1 C6 106.75(10) . . ?
C18 O3 C19 115.2(2) . . ?
C15 O5 C8 108.66(17) . . ?
C7 N1 S1 117.62(14) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 117.5(4) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 S1 119.8(2) . . ?
C1 C6 S1 118.5(2) . . ?
C8 C7 N1 128.51(19) . . ?
C8 C7 C17 107.61(19) . . ?
N1 C7 C17 123.87(19) . . ?
C7 C8 O5 107.98(18) . . ?
C7 C8 C9 136.3(2) . . ?
O5 C8 C9 115.73(18) . . ?
C14 C9 C10 118.3(2) . . ?
C14 C9 C8 121.1(2) . . ?
C10 C9 C8 120.6(2) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.7(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C17 C15 O5 109.36(19) . . ?
C17 C15 C16 134.7(2) . . ?
O5 C15 C16 116.0(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C7 106.38(19) . . ?
C15 C17 C18 130.2(2) . . ?
C7 C17 C18 123.2(2) . . ?
O4 C18 O3 124.2(2) . . ?
O4 C18 C17 122.2(2) . . ?
O3 C18 C17 113.5(2) . . ?
C20 C19 O3 108.7(3) . . ?
C20 C19 H19A 109.9 . . ?
O3 C19 H19A 109.9 . . ?
C20 C19 H19B 109.9 . . ?
O3 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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 1.4137(17) . ?
S1 O1 1.4200(18) . ?
S1 N1 1.650(2) . ?
S1 C6 1.749(2) . ?
O3 C18 1.316(3) . ?
O3 C19 1.463(3) . ?
O4 C18 1.210(3) . ?
O5 C15 1.365(3) . ?
O5 C8 1.381(2) . ?
N1 C7 1.427(3) . ?
C1 C2 1.344(4) . ?
C1 C6 1.385(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.357(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.351(3) . ?
C7 C17 1.441(3) . ?
C8 C9 1.465(3) . ?
C9 C14 1.384(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C17 1.349(3) . ?
C15 C16 1.482(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.472(3) . ?
C19 C20 1.453(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C7 -57.21(18) . . . . ?
O1 S1 N1 C7 174.68(15) . . . . ?
C6 S1 N1 C7 58.68(18) . . . . ?
C6 C1 C2 C3 -1.3(5) . . . . ?
C1 C2 C3 C4 2.4(6) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C1 1.7(4) . . . . ?
C4 C5 C6 S1 -176.4(2) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 S1 177.4(2) . . . . ?
O2 S1 C6 C5 -162.2(2) . . . . ?
O1 S1 C6 C5 -30.0(2) . . . . ?
N1 S1 C6 C5 82.4(2) . . . . ?
O2 S1 C6 C1 19.6(2) . . . . ?
O1 S1 C6 C1 151.8(2) . . . . ?
N1 S1 C6 C1 -95.8(2) . . . . ?
S1 N1 C7 C8 81.2(2) . . . . ?
S1 N1 C7 C17 -97.5(2) . . . . ?
N1 C7 C8 O5 -177.86(19) . . . . ?
C17 C7 C8 O5 1.0(2) . . . . ?
N1 C7 C8 C9 3.4(4) . . . . ?
C17 C7 C8 C9 -177.7(2) . . . . ?
C15 O5 C8 C7 -0.8(2) . . . . ?
C15 O5 C8 C9 178.30(17) . . . . ?
C7 C8 C9 C14 -168.3(2) . . . . ?
O5 C8 C9 C14 13.0(3) . . . . ?
C7 C8 C9 C10 13.1(4) . . . . ?
O5 C8 C9 C10 -165.6(2) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C8 C9 C10 C11 179.0(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C9 -0.3(4) . . . . ?
C10 C9 C14 C13 -0.1(4) . . . . ?
C8 C9 C14 C13 -178.7(2) . . . . ?
C8 O5 C15 C17 0.1(2) . . . . ?
C8 O5 C15 C16 -178.93(19) . . . . ?
O5 C15 C17 C7 0.5(2) . . . . ?
C16 C15 C17 C7 179.3(3) . . . . ?
O5 C15 C17 C18 -174.3(2) . . . . ?
C16 C15 C17 C18 4.5(4) . . . . ?
C8 C7 C17 C15 -1.0(2) . . . . ?
N1 C7 C17 C15 178.00(19) . . . . ?
C8 C7 C17 C18 174.30(19) . . . . ?
N1 C7 C17 C18 -6.7(3) . . . . ?
C19 O3 C18 O4 -1.1(4) . . . . ?
C19 O3 C18 C17 178.7(2) . . . . ?
C15 C17 C18 O4 158.4(2) . . . . ?
C7 C17 C18 O4 -15.6(3) . . . . ?
C15 C17 C18 O3 -21.3(3) . . . . ?
C7 C17 C18 O3 164.61(19) . . . . ?
C18 O3 C19 C20 177.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659254
