#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:15:31 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178427 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024841.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_4024841
loop_
_publ_author_name
'Neta Shefer'
'Tal Harel'
'Shlomo Rozen'
_publ_section_title
;
Synthesis of Oxygenated Fused Oligothiophenes with HOF.CH3CN
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6993
_journal_page_last               6998
_journal_paper_doi               10.1021/jo901106j
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C10 H9 O4 S3, C2 H3 N'
_chemical_formula_sum            'C12 H11 N O4 S3'
_chemical_formula_weight         329.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                   12.769(2)
_cell_length_b                   7.2172(13)
_cell_length_c                   15.297(3)
_cell_measurement_temperature    200(1)
_cell_volume                     1409.7(4)
_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      200(1)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_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            15954
_diffrn_reflns_theta_full        28.01
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_correction_T_min  0.8140
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.248
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0523P)²+1.5250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1300
_reflns_number_gt                1721
_reflns_number_total             1820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901106j_si_003.cif
_cod_data_source_block           n3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4024841
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
C1 C 0.6206(3) 0.2500 0.6955(3) 0.0239(8) Uani 1 2 d S . .
C2 C 0.6644(3) 0.2500 0.6164(3) 0.0216(8) Uani 1 2 d S . .
C3 C 0.5889(3) 0.2500 0.5449(2) 0.0193(7) Uani 1 2 d S . .
C4 C 0.4857(3) 0.2500 0.5698(2) 0.0181(7) Uani 1 2 d S . .
C5 C 0.4174(3) 0.2500 0.4980(2) 0.0186(7) Uani 1 2 d S . .
C6 C 0.4709(3) 0.2500 0.4196(2) 0.0191(7) Uani 1 2 d S . .
C7 C 0.4065(3) 0.2500 0.3405(2) 0.0229(8) Uani 1 2 d S . .
C8 C 0.3049(3) 0.2500 0.3575(2) 0.0238(8) Uani 1 2 d S . .
C9 C 0.6660(4) 0.2500 0.7847(3) 0.0446(13) Uani 1 2 d S . .
C10 C 0.2115(4) 0.2500 0.2995(3) 0.0390(11) Uani 1 2 d S . .
C11 C 0.4393(4) 0.2500 0.0495(3) 0.0460(12) Uani 1 2 d S . .
C12 C 0.4625(5) 0.2500 -0.0423(4) 0.0503(14) Uani 1 2 d S . .
H2 H 0.735(4) 0.2500 0.606(3) 0.034(13) Uiso 1 2 d S . .
H7 H 0.432(3) 0.2500 0.285(3) 0.021(11) Uiso 1 2 d S . .
H9A H 0.735(5) 0.2500 0.785(4) 0.056(17) Uiso 1 2 d S . .
H9B H 0.639(3) 0.143(6) 0.817(3) 0.055(12) Uiso 1 1 d . . .
H10A H 0.236(4) 0.2500 0.247(4) 0.045(15) Uiso 1 2 d S . .
H10B H 0.174(4) 0.139(7) 0.304(3) 0.076(15) Uiso 1 1 d . . .
H12A H 0.528(6) 0.2500 -0.050(4) 0.07(2) Uiso 1 2 d S . .
H12B H 0.437(4) 0.139(7) -0.067(3) 0.083(17) Uiso 1 1 d . . .
N1 N 0.4188(6) 0.2500 0.1205(3) 0.0804(18) Uani 1 2 d S . .
O1 O 0.43816(15) 0.0805(3) 0.71815(13) 0.0294(5) Uani 1 1 d . . .
O2 O 0.23335(15) 0.0803(3) 0.49944(13) 0.0300(5) Uani 1 1 d . . .
S1 S 0.48093(7) 0.2500 0.68483(6) 0.0189(2) Uani 1 2 d S . .
S2 S 0.28251(7) 0.2500 0.47284(6) 0.0205(2) Uani 1 2 d S . .
S3 S 0.60419(7) 0.2500 0.43398(6) 0.0220(2) Uani 1 2 d S . .
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
C2 C1 C9 132.2(4) . . ?
C2 C1 S1 109.6(3) . . ?
C9 C1 S1 118.3(3) . . ?
C1 C2 C3 113.8(3) . . ?
C1 C2 H2 124(3) . . ?
C3 C2 H2 122(3) . . ?
C4 C3 C2 115.3(3) . . ?
C4 C3 S3 112.7(3) . . ?
C2 C3 S3 132.1(3) . . ?
C3 C4 C5 112.4(3) . . ?
C3 C4 S1 108.1(3) . . ?
C5 C4 S1 139.5(3) . . ?
C6 C5 C4 111.9(3) . . ?
C6 C5 S2 107.1(3) . . ?
C4 C5 S2 141.1(3) . . ?
C5 C6 C7 116.1(3) . . ?
C5 C6 S3 112.3(3) . . ?
C7 C6 S3 131.6(3) . . ?
C8 C7 C6 112.8(3) . . ?
C8 C7 H7 122(3) . . ?
C6 C7 H7 125(3) . . ?
C7 C8 C10 132.0(4) . . ?
C7 C8 S2 110.5(3) . . ?
C10 C8 S2 117.5(3) . . ?
C1 C9 H9A 113(4) . . ?
C1 C9 H9B 109(2) . . ?
H9A C9 H9B 111(3) . . ?
C8 C10 H10A 105(4) . . ?
C8 C10 H10B 112(3) . . ?
H10A C10 H10B 105(3) . . ?
N1 C11 C12 178.4(7) . . ?
C11 C12 H12A 110(5) . . ?
C11 C12 H12B 109(3) . . ?
H12A C12 H12B 107(4) . . ?
O1 S1 O1 117.20(17) . 7_565 ?
O1 S1 C4 111.62(10) . . ?
O1 S1 C4 111.62(10) 7_565 . ?
O1 S1 C1 110.30(10) . . ?
O1 S1 C1 110.30(10) 7_565 . ?
C4 S1 C1 93.25(18) . . ?
O2 S2 O2 117.17(18) . 7_565 ?
O2 S2 C5 111.41(10) . . ?
O2 S2 C5 111.41(10) 7_565 . ?
O2 S2 C8 110.48(11) . . ?
O2 S2 C8 110.48(11) 7_565 . ?
C5 S2 C8 93.40(18) . . ?
C3 S3 C6 90.82(17) . . ?
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
C1 C2 1.333(6) . ?
C1 C9 1.483(6) . ?
C1 S1 1.791(4) . ?
C2 C3 1.459(5) . ?
C2 H2 0.92(5) . ?
C3 C4 1.372(5) . ?
C3 S3 1.708(4) . ?
C4 C5 1.402(5) . ?
C4 S1 1.761(4) . ?
C5 C6 1.381(5) . ?
C5 S2 1.765(4) . ?
C6 C7 1.462(5) . ?
C6 S3 1.716(4) . ?
C7 C8 1.324(6) . ?
C7 H7 0.91(4) . ?
C8 C10 1.486(6) . ?
C8 S2 1.787(4) . ?
C9 H9A 0.88(6) . ?
C9 H9B 0.98(4) . ?
C10 H10A 0.86(6) . ?
C10 H10B 0.94(5) . ?
C11 N1 1.116(7) . ?
C11 C12 1.435(8) . ?
C12 H12A 0.85(7) . ?
C12 H12B 0.95(5) . ?
O1 S1 1.434(2) . ?
O2 S2 1.435(2) . ?
S1 O1 1.434(2) 7_565 ?
S2 O2 1.435(2) 7_565 ?
