#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/00/7150059.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_7150059
loop_
_publ_author_name
'Foot, Jonathan S.'
'Giblin, Gerard M. P.'
'Whitwood, A. C.'
'Taylor, R. J. K.'
_publ_section_title
;
 Unexpected Z-stereoselectivity in the Ramberg-Bäcklund reaction of
 diarylsulfones leading to cis-stilbenes: the effect of aryl
 substituents and application in the synthesis of the integrastatin
 nucleus.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              756
_journal_page_last               763
_journal_paper_doi               10.1039/b418426b
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C17 H16 O2'
_chemical_formula_sum            'C17 H16 O2'
_chemical_formula_weight         252.30
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 115.7010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.3595(13)
_cell_length_b                   8.8441(6)
_cell_length_c                   16.7833(11)
_cell_measurement_reflns_used    5322
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.58
_cell_volume                     2589.3(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      115(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0151
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9228
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0383
_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)+(0.0608P)²+1.2020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                2861
_reflns_number_total             3209
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b418426b.txt
_cod_data_source_block           rjt0303m
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7150059
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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
O1 O 0.09599(4) 0.05535(8) 0.10370(4) 0.02317(17) Uani 1 1 d . . .
O2 O 0.09918(4) 0.09585(7) 0.24224(4) 0.02250(16) Uani 1 1 d . . .
C10 C 0.19767(5) 0.20793(10) 0.21104(6) 0.0233(2) Uani 1 1 d . . .
C7 C 0.04729(6) 0.38075(11) 0.17430(7) 0.0242(2) Uani 1 1 d . . .
C15 C 0.16541(5) 0.12702(11) 0.13197(6) 0.0224(2) Uani 1 1 d . . .
C3 C -0.04699(6) 0.27247(12) 0.03854(7) 0.0262(2) Uani 1 1 d . . .
H3 H -0.0674 0.1874 0.0011 0.031 Uiso 1 1 calc R . .
C14 C 0.20376(6) 0.11114(12) 0.07871(7) 0.0269(2) Uani 1 1 d . . .
H14 H 0.1816 0.0536 0.0257 0.032 Uiso 1 1 calc R . .
C1 C 0.05135(5) 0.09879(10) 0.15089(6) 0.02096(19) Uani 1 1 d . . .
C9 C 0.15652(6) 0.21459(11) 0.27018(6) 0.0239(2) Uani 1 1 d . . .
C2 C 0.01657(5) 0.25477(10) 0.12029(6) 0.0220(2) Uani 1 1 d . . .
C16 C -0.00672(6) -0.02632(11) 0.13233(6) 0.0248(2) Uani 1 1 d . . .
H16A H 0.0198 -0.1204 0.1594 0.037 Uiso 1 1 calc R . .
H16B H -0.0352 -0.0404 0.0683 0.037 Uiso 1 1 calc R . .
H16C H -0.0424 0.0007 0.1572 0.037 Uiso 1 1 calc R . .
C5 C -0.05053(6) 0.53867(12) 0.06612(8) 0.0318(2) Uani 1 1 d . . .
H5 H -0.0736 0.6352 0.0481 0.038 Uiso 1 1 calc R . .
C8 C 0.11575(6) 0.36495(11) 0.26267(7) 0.0268(2) Uani 1 1 d . . .
H8A H 0.0988 0.3722 0.3103 0.032 Uiso 1 1 calc R . .
H8B H 0.1520 0.4488 0.2705 0.032 Uiso 1 1 calc R . .
C4 C -0.08045(6) 0.41362(13) 0.01188(7) 0.0310(2) Uani 1 1 d . . .
H4 H -0.1239 0.4247 -0.0435 0.037 Uiso 1 1 calc R . .
C11 C 0.26835(6) 0.27871(12) 0.23365(7) 0.0295(2) Uani 1 1 d . . .
H11 H 0.2907 0.3369 0.2864 0.035 Uiso 1 1 calc R . .
C6 C 0.01304(6) 0.52208(11) 0.14642(7) 0.0291(2) Uani 1 1 d . . .
H6 H 0.0337 0.6080 0.1831 0.035 Uiso 1 1 calc R . .
C12 C 0.30635(6) 0.26537(12) 0.18054(8) 0.0322(2) Uani 1 1 d . . .
H12 H 0.3542 0.3146 0.1967 0.039 Uiso 1 1 calc R . .
C17 C 0.20927(6) 0.17804(13) 0.36620(7) 0.0314(2) Uani 1 1 d . . .
H17A H 0.1793 0.1740 0.4005 0.047 Uiso 1 1 calc R . .
H17B H 0.2486 0.2566 0.3905 0.047 Uiso 1 1 calc R . .
H17C H 0.2339 0.0799 0.3694 0.047 Uiso 1 1 calc R . .
C13 C 0.27449(6) 0.18002(13) 0.10371(7) 0.0308(2) Uani 1 1 d . . .
H13 H 0.3012 0.1687 0.0681 0.037 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'
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
C15 O1 C1 114.47(7) . . ?
C1 O2 C9 112.89(7) . . ?
C15 C10 C11 117.99(9) . . ?
C15 C10 C9 119.76(8) . . ?
C11 C10 C9 122.24(9) . . ?
C2 C7 C6 119.33(9) . . ?
C2 C7 C8 120.68(9) . . ?
C6 C7 C8 119.98(9) . . ?
O1 C15 C10 122.25(8) . . ?
O1 C15 C14 116.49(8) . . ?
C10 C15 C14 121.23(9) . . ?
C4 C3 C2 120.39(10) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C13 C14 C15 119.47(10) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
O2 C1 O1 108.84(7) . . ?
O2 C1 C16 106.90(7) . . ?
O1 C1 C16 105.01(7) . . ?
O2 C1 C2 111.73(7) . . ?
O1 C1 C2 109.62(7) . . ?
C16 C1 C2 114.41(8) . . ?
O2 C9 C10 107.77(7) . . ?
O2 C9 C17 104.86(8) . . ?
C10 C9 C17 112.48(8) . . ?
O2 C9 C8 107.99(8) . . ?
C10 C9 C8 112.30(8) . . ?
C17 C9 C8 111.01(8) . . ?
C7 C2 C3 119.56(9) . . ?
C7 C2 C1 120.15(8) . . ?
C3 C2 C1 120.28(8) . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C5 C4 119.72(10) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C8 C9 111.43(8) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C3 C4 C5 120.07(10) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C12 C11 C10 121.15(10) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C5 C6 C7 120.91(10) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C11 C12 C13 119.90(9) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C13 C14 120.20(10) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
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
O1 C15 1.3712(11) . ?
O1 C1 1.4544(11) . ?
O2 C1 1.4061(11) . ?
O2 C9 1.4503(11) . ?
C10 C15 1.3945(13) . ?
C10 C11 1.3992(14) . ?
C10 C9 1.5195(14) . ?
C7 C2 1.3962(13) . ?
C7 C6 1.3970(14) . ?
C7 C8 1.5068(14) . ?
C15 C14 1.3947(14) . ?
C3 C4 1.3881(14) . ?
C3 C2 1.3988(13) . ?
C3 H3 0.9500 . ?
C14 C13 1.3871(15) . ?
C14 H14 0.9500 . ?
C1 C16 1.5105(13) . ?
C1 C2 1.5232(13) . ?
C9 C17 1.5222(13) . ?
C9 C8 1.5235(14) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C5 C6 1.3836(16) . ?
C5 C4 1.3892(16) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C4 H4 0.9500 . ?
C11 C12 1.3852(16) . ?
C11 H11 0.9500 . ?
C6 H6 0.9500 . ?
C12 C13 1.3867(17) . ?
C12 H12 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C13 H13 0.9500 . ?
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
C1 O1 C15 C10 13.55(12) . . . . ?
C1 O1 C15 C14 -168.37(8) . . . . ?
C11 C10 C15 O1 -179.23(8) . . . . ?
C9 C10 C15 O1 1.80(14) . . . . ?
C11 C10 C15 C14 2.79(14) . . . . ?
C9 C10 C15 C14 -176.18(9) . . . . ?
O1 C15 C14 C13 -179.63(9) . . . . ?
C10 C15 C14 C13 -1.54(15) . . . . ?
C9 O2 C1 O1 69.14(9) . . . . ?
C9 O2 C1 C16 -177.93(7) . . . . ?
C9 O2 C1 C2 -52.04(10) . . . . ?
C15 O1 C1 O2 -47.16(10) . . . . ?
C15 O1 C1 C16 -161.33(7) . . . . ?
C15 O1 C1 C2 75.31(9) . . . . ?
C1 O2 C9 C10 -51.49(10) . . . . ?
C1 O2 C9 C17 -171.52(7) . . . . ?
C1 O2 C9 C8 70.04(9) . . . . ?
C15 C10 C9 O2 15.95(12) . . . . ?
C11 C10 C9 O2 -162.97(8) . . . . ?
C15 C10 C9 C17 131.05(9) . . . . ?
C11 C10 C9 C17 -47.87(12) . . . . ?
C15 C10 C9 C8 -102.86(10) . . . . ?
C11 C10 C9 C8 78.22(11) . . . . ?
C6 C7 C2 C3 1.20(14) . . . . ?
C8 C7 C2 C3 -179.99(9) . . . . ?
C6 C7 C2 C1 -177.86(8) . . . . ?
C8 C7 C2 C1 0.95(14) . . . . ?
C4 C3 C2 C7 -1.34(14) . . . . ?
C4 C3 C2 C1 177.72(8) . . . . ?
O2 C1 C2 C7 15.84(12) . . . . ?
O1 C1 C2 C7 -104.90(9) . . . . ?
C16 C1 C2 C7 137.48(9) . . . . ?
O2 C1 C2 C3 -163.21(8) . . . . ?
O1 C1 C2 C3 76.05(10) . . . . ?
C16 C1 C2 C3 -41.58(12) . . . . ?
C2 C7 C8 C9 15.97(13) . . . . ?
C6 C7 C8 C9 -165.24(9) . . . . ?
O2 C9 C8 C7 -48.47(11) . . . . ?
C10 C9 C8 C7 70.21(10) . . . . ?
C17 C9 C8 C7 -162.90(8) . . . . ?
C2 C3 C4 C5 0.49(15) . . . . ?
C6 C5 C4 C3 0.50(15) . . . . ?
C15 C10 C11 C12 -1.85(15) . . . . ?
C9 C10 C11 C12 177.09(9) . . . . ?
C4 C5 C6 C7 -0.63(15) . . . . ?
C2 C7 C6 C5 -0.23(15) . . . . ?
C8 C7 C6 C5 -179.04(9) . . . . ?
C10 C11 C12 C13 -0.34(16) . . . . ?
C11 C12 C13 C14 1.66(16) . . . . ?
C15 C14 C13 C12 -0.73(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10192890
