#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025709.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_4025709
loop_
_publ_author_name
'Pankaj Jain'
'Gregory M. Ferrence'
'Timothy D. Lash'
_publ_contact_author_address
;
CB 4160
Department of Chemistry
Illinois State University
Normal, IL 61790
;
_publ_contact_author_email       Ferrence@IllinoisState.edu
_publ_contact_author_fax         (309)4385538
_publ_contact_author_name        'Ferrence, Gregory M.'
_publ_contact_author_phone       (309)4387971
_publ_section_title
;
 Preparation of Furan and Thiophene-Derived Fulvene Dialdehydes: Synthesis
 and Structural Characterization of a 22-Oxa-21-carbaporphyrin and a
 Related Palladium(II) Organometallic Complex
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6563
_journal_page_last               6573
_journal_paper_doi               10.1021/jo101310m
_journal_volume                  75
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H10 O2 S1'
_chemical_formula_sum            'C16 H10 O2 S'
_chemical_formula_weight         266.3
_chemical_name_systematic        ?
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-06-28T16:43:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
?

2010-06-30 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.9676(5)
_cell_length_b                   15.4981(11)
_cell_length_c                   22.8186(17)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.2
_cell_measurement_theta_min      2.628
_cell_measurement_wavelength     0.71073
_cell_volume                     2464.1(3)
_computing_cell_refinement       'APEX2 & SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) 
;
_computing_publication_material
;
WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.018
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20193
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.3
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0437P)²+2.0963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                2494
_reflns_number_total             2813
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo101310m_si_001.cif
_cod_data_source_block           22
_cod_database_code               4025709
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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 0.8619(2) 0.48946(10) -0.16520(7) 0.0160(3) Uani 1 1 d . . .
C2 C 0.9049(2) 0.58251(10) -0.16730(7) 0.0158(3) Uani 1 1 d . . .
C3 C 0.8746(2) 0.61547(10) -0.11047(7) 0.0150(3) Uani 1 1 d . . .
C4 C 0.8163(2) 0.54353(10) -0.07191(7) 0.0144(3) Uani 1 1 d . . .
C5 C 0.7818(2) 0.55169(10) -0.01381(7) 0.0153(3) Uani 1 1 d . . .
H5 H 0.7969 0.6085 0.0012 0.018 Uiso 1 1 calc R . .
C6 C 0.7257(2) 0.48805(10) 0.02895(7) 0.0143(3) Uani 1 1 d . . .
C7 C 0.6955(2) 0.50683(10) 0.08751(7) 0.0158(3) Uani 1 1 d . . .
H7 H 0.7111 0.5629 0.1036 0.019 Uiso 1 1 calc R . .
C8 C 0.6396(2) 0.43478(10) 0.12079(7) 0.0168(3) Uani 1 1 d . . .
H8 H 0.6126 0.437 0.1616 0.02 Uiso 1 1 calc R . .
C9 C 0.6281(2) 0.36065(10) 0.08778(7) 0.0159(3) Uani 1 1 d . . .
C10 C 0.8112(2) 0.46746(10) -0.10954(7) 0.0155(3) Uani 1 1 d . . .
H10 H 0.7775 0.411 -0.0971 0.019 Uiso 1 1 calc R . .
C12 C 0.8732(3) 0.42732(10) -0.21302(7) 0.0198(3) Uani 1 1 d . . .
H12 H 0.8392 0.3693 -0.2044 0.024 Uiso 1 1 calc R . .
C14 C 0.5762(2) 0.27535(11) 0.10805(8) 0.0198(3) Uani 1 1 d . . .
H14 H 0.544 0.269 0.1483 0.024 Uiso 1 1 calc R . .
C2A C 0.9710(3) 0.63585(11) -0.21202(7) 0.0211(3) Uani 1 1 d . . .
H2A H 0.9945 0.6136 -0.2501 0.025 Uiso 1 1 calc R . .
C3A C 0.9055(2) 0.70224(10) -0.09822(7) 0.0183(3) Uani 1 1 d . . .
H3A H 0.8843 0.7246 -0.06 0.022 Uiso 1 1 calc R . .
C3B C 0.9686(2) 0.75573(10) -0.14366(8) 0.0210(3) Uani 1 1 d . . .
H3B H 0.989 0.8154 -0.1363 0.025 Uiso 1 1 calc R . .
C2B C 1.0018(3) 0.72291(11) -0.19936(8) 0.0233(4) Uani 1 1 d . . .
H2B H 1.0462 0.7604 -0.2294 0.028 Uiso 1 1 calc R . .
O13 O 0.9223(2) 0.44326(8) -0.26291(5) 0.0261(3) Uani 1 1 d . . .
O15 O 0.57067(19) 0.21085(8) 0.07726(6) 0.0262(3) Uani 1 1 d . . .
S11 S 0.68675(6) 0.37936(2) 0.015305(16) 0.01511(12) Uani 1 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C10 C1 C12 123.16(15) . . ?
C10 C1 C2 109.15(14) . . ?
C12 C1 C2 127.68(14) . . ?
C2A C2 C3 120.58(15) . . ?
C2A C2 C1 132.25(15) . . ?
C3 C2 C1 107.12(13) . . ?
C3A C3 C2 120.83(15) . . ?
C3A C3 C4 130.75(15) . . ?
C2 C3 C4 108.39(13) . . ?
C5 C4 C10 130.37(15) . . ?
C5 C4 C3 124.19(14) . . ?
C10 C4 C3 105.43(13) . . ?
C4 C5 C6 130.35(15) . . ?
C4 C5 H5 114.8 . . ?
C6 C5 H5 114.8 . . ?
C7 C6 C5 123.43(14) . . ?
C7 C6 S11 110.73(12) . . ?
C5 C6 S11 125.84(12) . . ?
C6 C7 C8 113.37(14) . . ?
C6 C7 H7 123.3 . . ?
C8 C7 H7 123.3 . . ?
C9 C8 C7 112.57(14) . . ?
C9 C8 H8 123.7 . . ?
C7 C8 H8 123.7 . . ?
C8 C9 C14 127.05(15) . . ?
C8 C9 S11 111.71(12) . . ?
C14 C9 S11 121.24(12) . . ?
C1 C10 C4 109.90(14) . . ?
C1 C10 H10 125.1 . . ?
C4 C10 H10 125.1 . . ?
O13 C12 C1 125.66(15) . . ?
O13 C12 H12 117.2 . . ?
C1 C12 H12 117.2 . . ?
O15 C14 C9 124.85(16) . . ?
O15 C14 H14 117.6 . . ?
C9 C14 H14 117.6 . . ?
C2 C2A C2B 118.24(16) . . ?
C2 C2A H2A 120.9 . . ?
C2B C2A H2A 120.9 . . ?
C3 C3A C3B 118.22(15) . . ?
C3 C3A H3A 120.9 . . ?
C3B C3A H3A 120.9 . . ?
C2B C3B C3A 120.93(15) . . ?
C2B C3B H3B 119.5 . . ?
C3A C3B H3B 119.5 . . ?
C3B C2B C2A 121.18(16) . . ?
C3B C2B H2B 119.4 . . ?
C2A C2B H2B 119.4 . . ?
C9 S11 C6 91.62(8) . . ?
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 C10 1.362(2) . ?
C1 C12 1.458(2) . ?
C1 C2 1.474(2) . ?
C2 C2A 1.392(2) . ?
C2 C3 1.410(2) . ?
C3 C3A 1.390(2) . ?
C3 C4 1.477(2) . ?
C4 C5 1.353(2) . ?
C4 C10 1.459(2) . ?
C5 C6 1.441(2) . ?
C5 H5 0.95 . ?
C6 C7 1.384(2) . ?
C6 S11 1.7343(15) . ?
C7 C8 1.406(2) . ?
C7 H7 0.95 . ?
C8 C9 1.376(2) . ?
C8 H8 0.95 . ?
C9 C14 1.446(2) . ?
C9 S11 1.7280(16) . ?
C10 H10 0.95 . ?
C12 O13 1.214(2) . ?
C12 H12 0.95 . ?
C14 O15 1.223(2) . ?
C14 H14 0.95 . ?
C2A C2B 1.396(2) . ?
C2A H2A 0.95 . ?
C3A C3B 1.399(2) . ?
C3A H3A 0.95 . ?
C3B C2B 1.388(3) . ?
C3B H3B 0.95 . ?
C2B H2B 0.95 . ?
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
C10 C1 C2 C2A 176.48(18) . . . . ?
C12 C1 C2 C2A -2.3(3) . . . . ?
C10 C1 C2 C3 -0.89(18) . . . . ?
C12 C1 C2 C3 -179.65(16) . . . . ?
C2A C2 C3 C3A 1.6(2) . . . . ?
C1 C2 C3 C3A 179.34(15) . . . . ?
C2A C2 C3 C4 -176.63(15) . . . . ?
C1 C2 C3 C4 1.11(17) . . . . ?
C3A C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C5 177.74(15) . . . . ?
C3A C3 C4 C10 -178.92(16) . . . . ?
C2 C3 C4 C10 -0.93(17) . . . . ?
C10 C4 C5 C6 -1.3(3) . . . . ?
C3 C4 C5 C6 -179.59(15) . . . . ?
C4 C5 C6 C7 179.99(16) . . . . ?
C4 C5 C6 S11 0.0(3) . . . . ?
C5 C6 C7 C8 179.30(14) . . . . ?
S11 C6 C7 C8 -0.71(18) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C7 C8 C9 C14 179.61(15) . . . . ?
C7 C8 C9 S11 0.08(18) . . . . ?
C12 C1 C10 C4 179.12(15) . . . . ?
C2 C1 C10 C4 0.30(18) . . . . ?
C5 C4 C10 C1 -178.18(16) . . . . ?
C3 C4 C10 C1 0.38(17) . . . . ?
C10 C1 C12 O13 -178.01(17) . . . . ?
C2 C1 C12 O13 0.6(3) . . . . ?
C8 C9 C14 O15 -178.83(17) . . . . ?
S11 C9 C14 O15 0.7(2) . . . . ?
C3 C2 C2A C2B -1.5(3) . . . . ?
C1 C2 C2A C2B -178.60(17) . . . . ?
C2 C3 C3A C3B -0.4(2) . . . . ?
C4 C3 C3A C3B 177.36(16) . . . . ?
C3 C3A C3B C2B -0.8(2) . . . . ?
C3A C3B C2B C2A 0.8(3) . . . . ?
C2 C2A C2B C3B 0.3(3) . . . . ?
C8 C9 S11 C6 -0.41(13) . . . . ?
C14 C9 S11 C6 -179.96(14) . . . . ?
C7 C6 S11 C9 0.63(12) . . . . ?
C5 C6 S11 C9 -179.37(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659276
