#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024721.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_4024721
loop_
_publ_author_name
'Yunhui Lang'
'Fabio E. S. Souza'
'Xinshe Xu'
'Nicholas J. Taylor'
'Abdeljalil Assoud'
'Russell Rodrigo'
_publ_section_title
;
Pentacyclic Furanosteroids: The Synthesis of Potential Kinase Inhibitors
Related to Viridin and Wortmannolone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5429
_journal_page_last               5439
_journal_paper_doi               10.1021/jo900922q
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C22 H24 O5 Si'
_chemical_formula_weight         396.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 122.394(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.0031(5)
_cell_length_b                   10.8154(3)
_cell_length_c                   12.0798(4)
_cell_measurement_temperature    180(2)
_cell_volume                     1875.73(10)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       Omega
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7593
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Needle plate fragment'
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_coef       0.0059(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.468
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5067
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.468
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0346
_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)+(0.0152P)²+0.2955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                4890
_reflns_number_total             5067
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900922q_si_005.cif
_cod_data_source_block           jalil
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'None' changed to 'none' 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      Cc
_cod_database_code               4024721
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'
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 0.05311(10) 0.73902(14) 0.34268(15) 0.0191(3) Uani 1 1 d . . .
H1 H 0.0936 0.6822 0.4173 0.023 Uiso 1 1 calc R . .
C2 C 0.07138(11) 0.70681(15) 0.23331(15) 0.0230(3) Uani 1 1 d . . .
H2 H 0.1362 0.7343 0.2645 0.028 Uiso 1 1 calc R . .
C3 C 0.00490(11) 0.77089(16) 0.09831(16) 0.0246(3) Uani 1 1 d . . .
H3 H 0.0332 0.8524 0.0999 0.030 Uiso 1 1 calc R . .
C3A C -0.08916(11) 0.79631(15) 0.07640(15) 0.0219(3) Uani 1 1 d . . .
C4 C -0.16307(11) 0.86252(16) -0.01801(16) 0.0253(3) Uani 1 1 d . . .
H4 H -0.1690 0.8908 -0.0966 0.030 Uiso 1 1 calc R . .
O5 O -0.22760(8) 0.88315(11) 0.01462(11) 0.0259(3) Uani 1 1 d . . .
C5A C -0.19171(11) 0.82795(15) 0.13464(15) 0.0219(3) Uani 1 1 d . . .
C6 C -0.22890(10) 0.84649(15) 0.21602(15) 0.0211(3) Uani 1 1 d . . .
C6A C -0.16779(10) 0.79377(14) 0.35082(15) 0.0188(3) Uani 1 1 d . . .
C6B C -0.19897(10) 0.79608(14) 0.43818(15) 0.0196(3) Uani 1 1 d . . .
C7 C -0.29362(11) 0.83415(16) 0.41172(16) 0.0239(3) Uani 1 1 d . . .
H7X H -0.3436 0.7819 0.3425 0.029 Uiso 1 1 calc R . .
H7Y H -0.3070 0.9218 0.3841 0.029 Uiso 1 1 calc R . .
C8 C -0.28548(11) 0.81473(18) 0.54361(17) 0.0286(4) Uani 1 1 d . . .
H8X H -0.2933 0.8942 0.5772 0.034 Uiso 1 1 calc R . .
H8Y H -0.3339 0.7565 0.5333 0.034 Uiso 1 1 calc R . .
C9 C -0.18966(12) 0.76249(16) 0.63657(17) 0.0254(3) Uani 1 1 d . . .
C9A C -0.14179(10) 0.75275(15) 0.56467(15) 0.0211(3) Uani 1 1 d . . .
C10 C -0.05363(11) 0.70482(15) 0.61015(15) 0.0230(3) Uani 1 1 d . . .
H10 H -0.0148 0.6778 0.6983 0.028 Uiso 1 1 calc R . .
C11 C -0.02402(10) 0.69755(15) 0.52414(15) 0.0221(3) Uani 1 1 d . . .
H11 H 0.0353 0.6628 0.5531 0.027 Uiso 1 1 calc R . .
C11A C -0.07966(10) 0.74052(14) 0.39462(15) 0.0188(3) Uani 1 1 d . . .
C11B C -0.04967(10) 0.70789(14) 0.29945(15) 0.0183(3) Uani 1 1 d . . .
C11C C -0.10978(10) 0.77356(14) 0.17355(15) 0.0193(3) Uani 1 1 d . . .
Si12 Si 0.09437(3) 0.90355(4) 0.40821(4) 0.02245(10) Uani 1 1 d . . .
C13 C 0.12607(14) 0.92063(18) 0.58126(17) 0.0323(4) Uani 1 1 d . . .
H13X H 0.1586 0.9993 0.6168 0.048 Uiso 1 1 calc R . .
H13Y H 0.1668 0.8523 0.6341 0.048 Uiso 1 1 calc R . .
H13Z H 0.0694 0.9193 0.5837 0.048 Uiso 1 1 calc R . .
C14 C 0.20217(12) 0.94024(18) 0.40887(18) 0.0311(4) Uani 1 1 d . . .
H14X H 0.2495 0.8769 0.4589 0.047 Uiso 1 1 calc R . .
H14Y H 0.2260 1.0213 0.4495 0.047 Uiso 1 1 calc R . .
H14Z H 0.1875 0.9417 0.3186 0.047 Uiso 1 1 calc R . .
C15 C 0.00458(13) 1.02431(16) 0.31091(19) 0.0345(4) Uani 1 1 d . . .
H15X H -0.0109 1.0231 0.2202 0.052 Uiso 1 1 calc R . .
H15Y H 0.0292 1.1059 0.3494 0.052 Uiso 1 1 calc R . .
H15Z H -0.0516 1.0073 0.3121 0.052 Uiso 1 1 calc R . .
O16 O 0.06894(9) 0.57599(11) 0.21900(12) 0.0345(3) Uani 1 1 d . . .
H16 H 0.0702 0.5649 0.1516 0.052 Uiso 1 1 d R . .
O17 O 0.00443(9) 0.69752(14) 0.00117(12) 0.0404(4) Uani 1 1 d . . .
H17 H -0.0355 0.7046 -0.0749 0.061 Uiso 1 1 d R . .
O18 O -0.30077(8) 0.90358(12) 0.18117(11) 0.0284(3) Uani 1 1 d . . .
O19 O -0.15793(9) 0.73471(13) 0.75074(12) 0.0359(3) Uani 1 1 d . . .
C20 C -0.07172(12) 0.56668(15) 0.27597(18) 0.0272(4) Uani 1 1 d . . .
H20X H -0.0702 0.5401 0.1996 0.041 Uiso 1 1 calc R . .
H20Y H -0.1337 0.5510 0.2601 0.041 Uiso 1 1 calc R . .
H20Z H -0.0251 0.5204 0.3535 0.041 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'
Si Si 0.0817 0.0704 '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 C11B 111.36(12) . . ?
C2 C1 Si12 111.32(11) . . ?
C11B C1 Si12 115.58(10) . . ?
C2 C1 H1 105.9 . . ?
C11B C1 H1 105.9 . . ?
Si12 C1 H1 105.9 . . ?
O16 C2 C1 108.71(13) . . ?
O16 C2 C3 110.88(13) . . ?
C1 C2 C3 115.25(13) . . ?
O16 C2 H2 107.2 . . ?
C1 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
O17 C3 C3A 115.17(14) . . ?
O17 C3 C2 107.26(13) . . ?
C3A C3 C2 111.85(13) . . ?
O17 C3 H3 107.4 . . ?
C3A C3 H3 107.4 . . ?
C2 C3 H3 107.4 . . ?
C4 C3A C11C 104.97(14) . . ?
C4 C3A C3 131.45(15) . . ?
C11C C3A C3 122.44(14) . . ?
C3A C4 O5 111.52(14) . . ?
C3A C4 H4 124.2 . . ?
O5 C4 H4 124.2 . . ?
C4 O5 C5A 105.20(12) . . ?
C11C C5A O5 110.54(14) . . ?
C11C C5A C6 125.05(15) . . ?
O5 C5A C6 123.48(14) . . ?
O18 C6 C5A 123.90(15) . . ?
O18 C6 C6A 123.28(14) . . ?
C5A C6 C6A 112.75(13) . . ?
C6B C6A C11A 118.26(13) . . ?
C6B C6A C6 119.09(13) . . ?
C11A C6A C6 122.66(13) . . ?
C9A C6B C6A 119.81(14) . . ?
C9A C6B C7 111.28(14) . . ?
C6A C6B C7 128.80(14) . . ?
C6B C7 C8 104.34(13) . . ?
C6B C7 H7X 110.9 . . ?
C8 C7 H7X 110.9 . . ?
C6B C7 H7Y 110.9 . . ?
C8 C7 H7Y 110.9 . . ?
H7X C7 H7Y 108.9 . . ?
C9 C8 C7 106.52(13) . . ?
C9 C8 H8X 110.4 . . ?
C7 C8 H8X 110.4 . . ?
C9 C8 H8Y 110.4 . . ?
C7 C8 H8Y 110.4 . . ?
H8X C8 H8Y 108.6 . . ?
O19 C9 C9A 126.72(16) . . ?
O19 C9 C8 125.56(15) . . ?
C9A C9 C8 107.72(14) . . ?
C6B C9A C10 122.29(15) . . ?
C6B C9A C9 110.06(14) . . ?
C10 C9A C9 127.62(15) . . ?
C11 C10 C9A 118.36(15) . . ?
C11 C10 H10 120.8 . . ?
C9A C10 H10 120.8 . . ?
C10 C11 C11A 121.39(14) . . ?
C10 C11 H11 119.3 . . ?
C11A C11 H11 119.3 . . ?
C11 C11A C6A 119.79(13) . . ?
C11 C11A C11B 117.69(13) . . ?
C6A C11A C11B 121.70(13) . . ?
C11C C11B C11A 109.68(12) . . ?
C11C C11B C20 108.40(13) . . ?
C11A C11B C20 102.60(12) . . ?
C11C C11B C1 105.75(12) . . ?
C11A C11B C1 117.46(13) . . ?
C20 C11B C1 112.73(12) . . ?
C5A C11C C3A 107.75(14) . . ?
C5A C11C C11B 125.76(14) . . ?
C3A C11C C11B 126.40(14) . . ?
C13 Si12 C15 106.46(9) . . ?
C13 Si12 C14 106.24(9) . . ?
C15 Si12 C14 108.82(9) . . ?
C13 Si12 C1 112.06(8) . . ?
C15 Si12 C1 113.15(8) . . ?
C14 Si12 C1 109.81(8) . . ?
Si12 C13 H13X 109.5 . . ?
Si12 C13 H13Y 109.5 . . ?
H13X C13 H13Y 109.5 . . ?
Si12 C13 H13Z 109.5 . . ?
H13X C13 H13Z 109.5 . . ?
H13Y C13 H13Z 109.5 . . ?
Si12 C14 H14X 109.5 . . ?
Si12 C14 H14Y 109.5 . . ?
H14X C14 H14Y 109.5 . . ?
Si12 C14 H14Z 109.5 . . ?
H14X C14 H14Z 109.5 . . ?
H14Y C14 H14Z 109.5 . . ?
Si12 C15 H15X 109.5 . . ?
Si12 C15 H15Y 109.5 . . ?
H15X C15 H15Y 109.5 . . ?
Si12 C15 H15Z 109.5 . . ?
H15X C15 H15Z 109.5 . . ?
H15Y C15 H15Z 109.5 . . ?
C2 O16 H16 104.3 . . ?
C3 O17 H17 121.4 . . ?
C11B C20 H20X 109.5 . . ?
C11B C20 H20Y 109.5 . . ?
H20X C20 H20Y 109.5 . . ?
C11B C20 H20Z 109.5 . . ?
H20X C20 H20Z 109.5 . . ?
H20Y C20 H20Z 109.5 . . ?
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 1.550(2) . ?
C1 C11B 1.569(2) . ?
C1 Si12 1.9210(16) . ?
C1 H1 1.0000 . ?
C2 O16 1.423(2) . ?
C2 C3 1.563(2) . ?
C2 H2 1.0000 . ?
C3 O17 1.413(2) . ?
C3 C3A 1.500(2) . ?
C3 H3 1.0000 . ?
C3A C4 1.363(2) . ?
C3A C11C 1.415(2) . ?
C4 O5 1.3683(19) . ?
C4 H4 0.9500 . ?
O5 C5A 1.3722(19) . ?
C5A C11C 1.344(2) . ?
C5A C6 1.440(2) . ?
C6 O18 1.2251(18) . ?
C6 C6A 1.498(2) . ?
C6A C6B 1.412(2) . ?
C6A C11A 1.417(2) . ?
C6B C9A 1.381(2) . ?
C6B C7 1.520(2) . ?
C7 C8 1.538(2) . ?
C7 H7X 0.9900 . ?
C7 H7Y 0.9900 . ?
C8 C9 1.508(2) . ?
C8 H8X 0.9900 . ?
C8 H8Y 0.9900 . ?
C9 O19 1.219(2) . ?
C9 C9A 1.478(2) . ?
C9A C10 1.391(2) . ?
C10 C11 1.378(2) . ?
C10 H10 0.9500 . ?
C11 C11A 1.405(2) . ?
C11 H11 0.9500 . ?
C11A C11B 1.528(2) . ?
C11B C11C 1.482(2) . ?
C11B C20 1.562(2) . ?
Si12 C13 1.8675(18) . ?
Si12 C15 1.8696(18) . ?
Si12 C14 1.8713(18) . ?
C13 H13X 0.9800 . ?
C13 H13Y 0.9800 . ?
C13 H13Z 0.9800 . ?
C14 H14X 0.9800 . ?
C14 H14Y 0.9800 . ?
C14 H14Z 0.9800 . ?
C15 H15X 0.9800 . ?
C15 H15Y 0.9800 . ?
C15 H15Z 0.9800 . ?
O16 H16 0.8348 . ?
O17 H17 0.8018 . ?
C20 H20X 0.9800 . ?
C20 H20Y 0.9800 . ?
C20 H20Z 0.9800 . ?
