#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/70/1507008.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_1507008
loop_
_publ_author_name
'Magomedov, Nabi A.'
'Ruggiero, Piero L.'
'Tang, Yuchen'
_publ_section_title
;
 Chemoselective cyclizations of divinyl ketones to cyclohexenones mediated
 by Lewis acid and base.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              3373
_journal_page_last               3375
_journal_paper_doi               10.1021/ol048545b
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         'C24 H26 O3 S'
_chemical_formula_sum            'C24 H26 O3 S'
_chemical_formula_weight         394.51
_chemical_name_common            MAGYT03
_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                 101.066(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7139(8)
_cell_length_b                   12.3265(12)
_cell_length_c                   19.2851(19)
_cell_measurement_reflns_used    4604
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      23.92
_cell_measurement_theta_min      2.41
_cell_volume                     2032.9(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      193(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0724
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24213
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.0671
_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)+(0.0820P)²+0.1124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1654
_reflns_number_gt                2968
_reflns_number_total             5007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048545bsi20040803_115013.cif
_cod_data_source_block           ideal
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1507008
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
S1 S 0.94304(7) 0.51437(5) 0.14837(3) 0.0327(2) Uani 1 1 d .
O3 O 1.0372(2) 0.57980(15) 0.20185(10) 0.0477(5) Uani 1 1 d .
O2 O 0.8895(2) 0.55947(15) 0.07925(10) 0.0471(5) Uani 1 1 d .
C12 C 0.6355(3) 0.5229(2) 0.28244(12) 0.0299(6) Uani 1 1 d .
C2 C 0.7746(3) 0.4717(2) 0.18401(12) 0.0287(5) Uani 1 1 d .
H2B H 0.8129 0.4167 0.2214 0.034 Uiso 1 1 calc R
C23 C 1.0569(3) 0.3604(2) 0.07087(13) 0.0347(6) Uani 1 1 d .
H23A H 0.9973 0.3957 0.0308 0.042 Uiso 1 1 calc R
C4 C 0.5830(3) 0.6343(2) 0.16983(12) 0.0319(6) Uani 1 1 d .
H4A H 0.5146 0.6697 0.1994 0.038 Uiso 1 1 calc R
C10 C 0.4779(3) 0.5686(2) 0.11468(13) 0.0319(6) Uani 1 1 d .
O1 O 0.6898(2) 0.32175(15) 0.10896(11) 0.0523(6) Uani 1 1 d .
C18 C 1.0496(3) 0.3952(2) 0.13839(13) 0.0309(6) Uani 1 1 d .
C21 C 1.2379(3) 0.2197(2) 0.11992(15) 0.0386(6) Uani 1 1 d .
C1 C 0.6602(3) 0.4132(2) 0.12621(13) 0.0342(6) Uani 1 1 d .
C3 C 0.7040(3) 0.56535(19) 0.22034(12) 0.0298(6) Uani 1 1 d .
H3B H 0.7922 0.6148 0.2405 0.036 Uiso 1 1 calc R
C11 C 0.5177(3) 0.4699(2) 0.09508(13) 0.0345(6) Uani 1 1 d .
H11A H 0.4477 0.4344 0.0582 0.041 Uiso 1 1 calc R
C22 C 1.1518(3) 0.2737(2) 0.06249(14) 0.0402(7) Uani 1 1 d .
H22A H 1.1581 0.2505 0.0161 0.048 Uiso 1 1 calc R
C17 C 0.6597(3) 0.5834(2) 0.34436(14) 0.0407(7) Uani 1 1 d .
H17A H 0.7174 0.6491 0.3470 0.049 Uiso 1 1 calc R
C5 C 0.6609(3) 0.7266(2) 0.13444(15) 0.0416(7) Uani 1 1 d .
H5A H 0.7562 0.7501 0.1677 0.050 Uiso 1 1 calc R
H5B H 0.6945 0.6967 0.0921 0.050 Uiso 1 1 calc R
C19 C 1.1353(3) 0.3437(2) 0.19648(14) 0.0407(7) Uani 1 1 d .
H19A H 1.1318 0.3691 0.2427 0.049 Uiso 1 1 calc R
C13 C 0.5501(3) 0.4276(2) 0.28025(14) 0.0404(7) Uani 1 1 d .
H13A H 0.5306 0.3857 0.2381 0.049 Uiso 1 1 calc R
C15 C 0.5183(3) 0.4530(3) 0.39987(15) 0.0508(8) Uani 1 1 d .
H15A H 0.4796 0.4288 0.4400 0.061 Uiso 1 1 calc R
C6 C 0.5605(4) 0.8260(2) 0.11219(16) 0.0512(8) Uani 1 1 d .
H6A H 0.5306 0.8579 0.1548 0.061 Uiso 1 1 calc R
H6B H 0.6248 0.8804 0.0929 0.061 Uiso 1 1 calc R
C20 C 1.2261(3) 0.2551(2) 0.18754(14) 0.0434(7) Uani 1 1 d .
H20A H 1.2813 0.2177 0.2278 0.052 Uiso 1 1 calc R
C14 C 0.4927(4) 0.3925(3) 0.33875(15) 0.0500(8) Uani 1 1 d .
H14A H 0.4356 0.3266 0.3366 0.060 Uiso 1 1 calc R
C9 C 0.3220(3) 0.6145(2) 0.07976(16) 0.0447(7) Uani 1 1 d .
H9A H 0.3042 0.5938 0.0292 0.054 Uiso 1 1 calc R
H9B H 0.2406 0.5776 0.1006 0.054 Uiso 1 1 calc R
C16 C 0.6003(4) 0.5488(3) 0.40244(14) 0.0515(8) Uani 1 1 d .
H16A H 0.6164 0.5916 0.4442 0.062 Uiso 1 1 calc R
C8 C 0.2944(3) 0.7344(3) 0.08320(17) 0.0551(9) Uani 1 1 d .
H8A H 0.2918 0.7538 0.1328 0.066 Uiso 1 1 calc R
H8B H 0.1900 0.7508 0.0546 0.066 Uiso 1 1 calc R
C24 C 1.3427(4) 0.1257(2) 0.11066(18) 0.0571(8) Uani 1 1 d .
H24A H 1.3368 0.1119 0.0602 0.086 Uiso 1 1 calc R
H24B H 1.3087 0.0609 0.1330 0.086 Uiso 1 1 calc R
H24C H 1.4508 0.1431 0.1328 0.086 Uiso 1 1 calc R
C7 C 0.4133(4) 0.8061(2) 0.05790(17) 0.0600(9) Uani 1 1 d .
H7A H 0.4426 0.7724 0.0157 0.072 Uiso 1 1 calc R
H7B H 0.3639 0.8769 0.0432 0.072 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'
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
O3 S1 O2 119.20(13)
O3 S1 C18 107.77(12)
O2 S1 C18 107.70(12)
O3 S1 C2 106.44(11)
O2 S1 C2 108.76(12)
C18 S1 C2 106.30(11)
C13 C12 C17 118.2(2)
C13 C12 C3 123.6(2)
C17 C12 C3 118.2(2)
C1 C2 C3 115.1(2)
C1 C2 S1 108.83(16)
C3 C2 S1 112.22(16)
C22 C23 C18 119.2(2)
C10 C4 C3 113.5(2)
C10 C4 C5 110.1(2)
C3 C4 C5 112.2(2)
C11 C10 C4 122.3(2)
C11 C10 C9 118.4(2)
C4 C10 C9 119.3(2)
C19 C18 C23 120.4(2)
C19 C18 S1 120.6(2)
C23 C18 S1 118.70(19)
C22 C21 C20 118.1(2)
C22 C21 C24 121.5(3)
C20 C21 C24 120.4(3)
O1 C1 C11 122.8(2)
O1 C1 C2 119.6(2)
C11 C1 C2 117.5(2)
C12 C3 C2 110.51(19)
C12 C3 C4 111.10(19)
C2 C3 C4 114.17(19)
C10 C11 C1 124.6(2)
C23 C22 C21 121.6(2)
C16 C17 C12 120.7(3)
C6 C5 C4 116.1(2)
C18 C19 C20 119.9(2)
C12 C13 C14 120.9(3)
C14 C15 C16 119.5(3)
C7 C6 C5 115.5(2)
C19 C20 C21 120.7(2)
C15 C14 C13 120.2(3)
C8 C9 C10 119.3(2)
C15 C16 C17 120.4(3)
C9 C8 C7 115.9(3)
C6 C7 C8 114.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4360(19)
S1 O2 1.4368(18)
S1 C18 1.768(3)
S1 C2 1.814(2)
C12 C13 1.388(4)
C12 C17 1.389(3)
C12 C3 1.529(3)
C2 C1 1.526(3)
C2 C3 1.539(3)
C23 C22 1.379(4)
C23 C18 1.384(3)
C4 C10 1.501(3)
C4 C3 1.545(3)
C4 C5 1.549(3)
C10 C11 1.339(3)
C10 C9 1.506(4)
O1 C1 1.217(3)
C18 C19 1.377(3)
C21 C22 1.384(4)
C21 C20 1.398(4)
C21 C24 1.507(4)
C1 C11 1.450(4)
C17 C16 1.388(4)
C5 C6 1.518(4)
C19 C20 1.378(4)
C13 C14 1.388(4)
C15 C14 1.376(4)
C15 C16 1.377(4)
C6 C7 1.512(4)
C9 C8 1.500(4)
C8 C7 1.513(4)
