#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/74/1507433.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_1507433
loop_
_publ_author_name
'Lee, Dong Joon'
'Kim, Kyongtae'
'Park, Yung Ja'
_publ_section_title
;
 Novel Synthesis of 5,6-Dihydro-4H-thieno[3,2-b]pyrrol-5-ones via the
 Rhodium(II)-Mediated Wolff Rearrangement of
 3-(Thieno-2-yl)-3-oxo-2-diazopropanoates
;
_journal_issue                   6
_journal_name_full               'Organic Letters'
_journal_page_first              873
_journal_paper_doi               10.1021/ol016995n
_journal_volume                  4
_journal_year                    2002
_chemical_formula_sum            'C16 H14 N O3 S'
_chemical_formula_weight         300.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.46(2)
_cell_angle_beta                 100.41(2)
_cell_angle_gamma                106.86(2)
_cell_formula_units_Z            2
_cell_length_a                   8.187(2)
_cell_length_b                   9.357(3)
_cell_length_c                   10.880(3)
_cell_measurement_temperature    293(2)
_cell_volume                     715.7(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0024
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1744
_diffrn_reflns_theta_full        21.99
_diffrn_reflns_theta_max         21.99
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.235
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             314
_exptl_crystal_size_max          0.35mm
_exptl_crystal_size_mid          0.31mm
_exptl_crystal_size_min          0.18mm
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         1743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0740P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1319
_reflns_number_gt                1237
_reflns_number_total             1743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol016995n_s2.cif
_cod_data_source_block           snu2-15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        715.7(3)
_cod_original_sg_symbol_H-M      '? P(-1)'
_cod_database_code               1507433
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_calc_flag
S1 S 0.22096(16) 0.30099(14) 0.18282(11) 0.0394(4) Uani 1 d
N1 N 0.6370(5) 0.6942(4) 0.3521(3) 0.0385(10) Uani 1 d
O1 O 0.8093(4) 0.7446(4) 0.5645(3) 0.0492(9) Uani 1 d
O2 O 0.5705(4) 0.2456(4) 0.4422(3) 0.0517(9) Uani 1 d
O3 O 0.7402(5) 0.3871(4) 0.3511(4) 0.0591(10) Uani 1 d
C1 C 0.0907(6) 0.3226(5) -0.0617(4) 0.0369(11) Uani 1 d
C2 C 0.0848(7) 0.4076(6) -0.1454(5) 0.0517(14) Uani 1 d
C3 C -0.0531(8) 0.3373(7) -0.2683(5) 0.0586(16) Uani 1 d
C4 C -0.1846(8) 0.1889(6) -0.3075(5) 0.0512(14) Uani 1 d
C5 C -0.1796(8) 0.1046(7) -0.2263(5) 0.0597(16) Uani 1 d
C6 C -0.0429(7) 0.1709(6) -0.1046(5) 0.0519(14) Uani 1 d
C7 C 0.2348(6) 0.3961(5) 0.0702(4) 0.0360(11) Uani 1 d
C8 C 0.3788(6) 0.5400(6) 0.1248(4) 0.0383(12) Uani 1 d
C9 C 0.4770(6) 0.5729(5) 0.2582(4) 0.0350(11) Uani 1 d
C10 C 0.7284(9) 0.8484(7) 0.3458(7) 0.0492(14) Uani 1 d
C11 C 0.4084(5) 0.4579(5) 0.3045(4) 0.0322(11) Uani 1 d
C12 C 0.6807(6) 0.6606(5) 0.4635(5) 0.0385(11) Uani 1 d
C13 C 0.5378(5) 0.4929(5) 0.4390(4) 0.0338(11) Uani 1 d
C14 C 0.6182(6) 0.3607(6) 0.4143(4) 0.0372(11) Uani 1 d
C15 C 0.8110(10) 0.2603(9) 0.3066(9) 0.075(2) Uani 1 d
C16 C 0.6985(16) 0.1335(12) 0.1703(10) 0.107(3) Uani 1 d
H2 H 0.189(7) 0.519(6) -0.120(5) 0.074(16) Uiso 1 d
H3 H -0.046(6) 0.391(6) -0.323(5) 0.057(15) Uiso 1 d
H4 H -0.280(7) 0.138(6) -0.392(6) 0.073(17) Uiso 1 d
H5 H -0.260(7) 0.005(6) -0.262(5) 0.056(16) Uiso 1 d
H6 H -0.044(6) 0.110(6) -0.050(5) 0.062(15) Uiso 1 d
H8 H 0.406(5) 0.606(4) 0.081(4) 0.024(11) Uiso 1 d
H101 H 0.814(9) 0.913(7) 0.425(7) 0.10(2) Uiso 1 d
H102 H 0.760(7) 0.833(7) 0.268(6) 0.08(2) Uiso 1 d
H103 H 0.652(8) 0.905(7) 0.350(6) 0.08(2) Uiso 1 d
H151 H 0.828(8) 0.236(7) 0.383(6) 0.08(2) Uiso 1 d
H152 H 0.928(8) 0.318(6) 0.310(5) 0.078(19) Uiso 1 d
H161 H 0.743(9) 0.048(9) 0.133(7) 0.12(3) Uiso 1 d
H162 H 0.700(8) 0.184(8) 0.106(7) 0.10(2) Uiso 1 d
H163 H 0.583(8) 0.072(7) 0.177(6) 0.09(2) Uiso 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'
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
C11 S1 C7 91.3(2) . .
C12 N1 C9 110.0(3) . .
C12 N1 C10 123.8(4) . .
C9 N1 C10 125.4(4) . .
C14 O3 C15 116.3(4) . .
C6 C1 C2 118.2(4) . .
C6 C1 C7 121.5(4) . .
C2 C1 C7 120.3(4) . .
C3 C2 C1 119.5(5) . .
C4 C3 C2 121.3(5) . .
C3 C4 C5 119.5(5) . .
C4 C5 C6 120.2(5) . .
C1 C6 C5 121.2(5) . .
C8 C7 C1 128.9(4) . .
C8 C7 S1 111.8(3) . .
C1 C7 S1 119.2(3) . .
C7 C8 C9 111.4(4) . .
C11 C9 N1 111.4(3) . .
C11 C9 C8 114.5(4) . .
N1 C9 C8 133.9(4) . .
C9 C11 C13 109.8(4) . .
C9 C11 S1 111.1(3) . .
C13 C11 S1 138.1(3) . .
O1 C12 N1 126.2(4) . .
O1 C12 C13 125.0(4) . .
N1 C12 C13 108.8(4) . .
C11 C13 C14 108.3(3) . .
C11 C13 C13 116.6(4) . 2_666
C14 C13 C13 109.9(4) . 2_666
C11 C13 C12 99.6(3) . .
C14 C13 C12 110.7(3) . .
C13 C13 C12 111.4(4) 2_666 .
O2 C14 O3 124.8(4) . .
O2 C14 C13 124.4(4) . .
O3 C14 C13 110.7(4) . .
O3 C15 C16 111.3(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C11 1.711(4) .
S1 C7 1.739(4) .
N1 C12 1.364(5) .
N1 C9 1.389(5) .
N1 C10 1.450(6) .
O1 C12 1.208(5) .
O2 C14 1.192(5) .
O3 C14 1.323(5) .
O3 C15 1.448(7) .
C1 C6 1.379(6) .
C1 C2 1.397(6) .
C1 C7 1.478(6) .
C2 C3 1.390(7) .
C3 C4 1.357(7) .
C4 C5 1.370(7) .
C5 C6 1.380(7) .
C7 C8 1.360(6) .
C8 C9 1.409(6) .
C9 C11 1.356(5) .
C11 C13 1.514(6) .
C12 C13 1.564(6) .
C13 C14 1.533(6) .
C13 C13 1.545(8) 2_666
C15 C16 1.468(11) .
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_4
C6 C1 C2 C3 -0.4(7) . .
C7 C1 C2 C3 -179.2(5) . .
C1 C2 C3 C4 1.4(8) . .
C2 C3 C4 C5 -1.6(9) . .
C3 C4 C5 C6 0.8(9) . .
C2 C1 C6 C5 -0.4(8) . .
C7 C1 C6 C5 178.4(5) . .
C4 C5 C6 C1 0.2(9) . .
C6 C1 C7 C8 177.2(5) . .
C2 C1 C7 C8 -4.1(7) . .
C6 C1 C7 S1 -7.8(6) . .
C2 C1 C7 S1 171.0(4) . .
C11 S1 C7 C8 0.9(4) . .
C11 S1 C7 C1 -174.9(4) . .
C1 C7 C8 C9 175.0(4) . .
S1 C7 C8 C9 -0.3(5) . .
C12 N1 C9 C11 1.1(5) . .
C10 N1 C9 C11 -168.6(5) . .
C12 N1 C9 C8 -174.5(5) . .
C10 N1 C9 C8 15.7(8) . .
C7 C8 C9 C11 -0.6(6) . .
C7 C8 C9 N1 174.9(5) . .
N1 C9 C11 C13 -4.7(5) . .
C8 C9 C11 C13 171.9(4) . .
N1 C9 C11 S1 -175.3(3) . .
C8 C9 C11 S1 1.3(5) . .
C7 S1 C11 C9 -1.2(3) . .
C7 S1 C11 C13 -167.9(5) . .
C9 N1 C12 O1 -177.9(4) . .
C10 N1 C12 O1 -8.0(8) . .
C9 N1 C12 C13 2.8(5) . .
C10 N1 C12 C13 172.7(5) . .
C9 C11 C13 C14 -109.9(4) . .
S1 C11 C13 C14 56.8(6) . .
C9 C11 C13 C13 125.6(5) . 2_666
S1 C11 C13 C13 -67.6(7) . 2_666
C9 C11 C13 C12 5.8(4) . .
S1 C11 C13 C12 172.5(4) . .
O1 C12 C13 C11 175.6(4) . .
N1 C12 C13 C11 -5.1(4) . .
O1 C12 C13 C14 -70.6(5) . .
N1 C12 C13 C14 108.7(4) . .
O1 C12 C13 C13 52.0(6) . 2_666
N1 C12 C13 C13 -128.7(4) . 2_666
C15 O3 C14 O2 3.7(7) . .
C15 O3 C14 C13 -172.7(5) . .
C11 C13 C14 O2 -100.8(5) . .
C13 C13 C14 O2 27.6(6) 2_666 .
C12 C13 C14 O2 151.1(4) . .
C11 C13 C14 O3 75.7(4) . .
C13 C13 C14 O3 -155.9(4) 2_666 .
C12 C13 C14 O3 -32.4(5) . .
C14 O3 C15 C16 86.7(7) . .
