#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:17:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178893 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/22/4112244.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_4112244
loop_
_publ_author_name
'Nabi A. Magomedov'
'Piero L. Ruggiero'
'Yuchen Tang'
_publ_section_title
;
 Remarkably Facile Hexatriene Electrocyclizations as a Route to
 Functionalized Cyclohexenones via Ring Expansion of Cyclobutenones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1624
_journal_page_last               1625
_journal_paper_doi               10.1021/ja0399066
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C14 H14 O3 S'
_chemical_formula_sum            'C14 H14 O3 S'
_chemical_formula_weight         262.31
_chemical_name_common            MAGPR02
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                79.550(2)
_cell_angle_beta                 84.044(2)
_cell_angle_gamma                85.155(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8553(7)
_cell_length_b                   8.3097(8)
_cell_length_c                   11.1075(11)
_cell_measurement_reflns_used    4925
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.5
_cell_volume                     617.49(11)
_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      193(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7511
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      0
_exptl_crystal_description       Needle
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0380
_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)+(0.0478P)²+0.1581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                2436
_reflns_number_total             2956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0399066si20040113_120804.cif
_cod_data_source_block           asd1
_cod_original_cell_volume        617.50(11)
_cod_database_code               4112244
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.45947(5) 0.76538(5) 0.06758(3) 0.02925(12) Uani 1 1 d .
O1 O 0.62307(16) 0.71135(15) -0.01098(11) 0.0428(3) Uani 1 1 d .
O2 O 0.49329(18) 0.88464(14) 0.14087(11) 0.0418(3) Uani 1 1 d .
O8 O 0.58929(18) 0.51391(16) 0.30867(12) 0.0472(3) Uani 1 1 d .
C1 C 0.2505(2) 0.8314(2) -0.01809(17) 0.0423(4) Uani 1 1 d .
H1B H 0.2890 0.8452 -0.1057 0.059(6) Uiso 1 1 d R
H1C H 0.1908 0.9348 0.0012 0.062(6) Uiso 1 1 d R
C2 C 0.1083(2) 0.6957(2) 0.02080(15) 0.0409(4) Uani 1 1 d .
H2B H -0.0255 0.7406 0.0106 0.040(5) Uiso 1 1 d R
H2C H 0.1382 0.6113 -0.0295 0.065(7) Uiso 1 1 d R
C3 C 0.1302(2) 0.6231(2) 0.15649(15) 0.0360(4) Uani 1 1 d .
H3A H 0.0692 0.5179 0.1764 0.039(5) Uiso 1 1 d R
C4 C 0.3518(2) 0.59070(18) 0.16567(14) 0.0317(3) Uani 1 1 d .
H4B H 0.3957 0.4923 0.1307 0.039(5) Uiso 1 1 d R
C5 C 0.4205(2) 0.56919(19) 0.29282(15) 0.0346(3) Uani 1 1 d .
C6 C 0.2824(2) 0.6162(2) 0.39058(15) 0.0362(4) Uani 1 1 d .
H6A H 0.3182 0.5904 0.4706 0.038(5) Uiso 1 1 d R
C7 C 0.1043(2) 0.69551(19) 0.37174(15) 0.0325(3) Uani 1 1 d .
C8 C 0.0347(2) 0.7351(2) 0.24470(15) 0.0402(4) Uani 1 1 d .
H8A H -0.1065 0.7273 0.2516 0.060(6) Uiso 1 1 d R
H8B H 0.0610 0.8477 0.2095 0.054(6) Uiso 1 1 d R
C9 C -0.0231(2) 0.75127(19) 0.47486(15) 0.0348(4) Uani 1 1 d .
C10 C 0.0560(3) 0.7675(2) 0.58257(16) 0.0456(4) Uani 1 1 d .
H10A H 0.1899 0.7445 0.5891 0.062(6) Uiso 1 1 d R
C11 C -0.0619(3) 0.8176(2) 0.68006(18) 0.0542(5) Uani 1 1 d .
H11A H -0.0062 0.8274 0.7509 0.061(6) Uiso 1 1 d R
C12 C -0.2607(3) 0.8521(2) 0.67301(19) 0.0541(5) Uani 1 1 d .
H12A H -0.3392 0.8860 0.7383 0.064(6) Uiso 1 1 d R
C13 C -0.3409(3) 0.8363(3) 0.5679(2) 0.0563(5) Uani 1 1 d .
H13A H -0.4753 0.8584 0.5627 0.063(6) Uiso 1 1 d R
C14 C -0.2249(3) 0.7881(2) 0.46870(18) 0.0461(4) Uani 1 1 d .
H14A H -0.2818 0.7795 0.3979 0.048(5) Uiso 1 1 d 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'
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
O2 S1 O1 117.59(7)
O2 S1 C1 110.56(9)
O1 S1 C1 110.53(8)
O2 S1 C4 109.46(7)
O1 S1 C4 110.23(7)
C1 S1 C4 96.44(8)
C2 C1 S1 105.42(12)
C1 C2 C3 107.84(13)
C4 C3 C8 112.39(13)
C4 C3 C2 105.25(13)
C8 C3 C2 113.04(15)
C5 C4 C3 116.44(13)
C5 C4 S1 110.14(10)
C3 C4 S1 104.74(10)
O8 C5 C6 123.17(16)
O8 C5 C4 118.89(15)
C6 C5 C4 117.94(14)
C7 C6 C5 123.70(15)
C6 C7 C9 120.75(15)
C6 C7 C8 120.68(15)
C9 C7 C8 118.52(14)
C7 C8 C3 114.33(14)
C10 C9 C14 117.57(16)
C10 C9 C7 120.60(15)
C14 C9 C7 121.82(16)
C11 C10 C9 121.14(18)
C12 C11 C10 120.6(2)
C13 C12 C11 119.01(18)
C12 C13 C14 121.24(19)
C13 C14 C9 120.42(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4385(11)
S1 O1 1.4404(12)
S1 C1 1.7940(17)
S1 C4 1.8110(16)
O8 C5 1.2265(19)
C1 C2 1.527(2)
C2 C3 1.536(2)
C3 C4 1.530(2)
C3 C8 1.533(2)
C4 C5 1.510(2)
C5 C6 1.451(2)
C6 C7 1.355(2)
C7 C9 1.485(2)
C7 C8 1.507(2)
C9 C10 1.396(2)
C9 C14 1.398(2)
C10 C11 1.387(3)
C11 C12 1.376(3)
C12 C13 1.373(3)
C13 C14 1.390(3)
