#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024718.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_4024718
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 H22 O3 Si'
_chemical_formula_weight         362.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 102.6490(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8090(5)
_cell_length_b                   21.1057(12)
_cell_length_c                   12.4980(7)
_cell_measurement_temperature    180(2)
_cell_volume                     2009.9(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12170
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0060(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.274
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0641
_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)+(0.0194P)²+1.3774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                3162
_reflns_number_total             3952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900922q_si_002.cif
_cod_data_source_block           rr1248zm_jalil
_cod_original_sg_symbol_H-M      P2_1/c
_cod_database_code               4024718
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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 0.3599(3) 0.63041(13) 0.18592(19) 0.0479(7) Uani 1 1 d . . .
H1 H 0.2550 0.6430 0.2147 0.057 Uiso 1 1 calc R . .
C2 C 0.3110(4) 0.64103(15) 0.0625(2) 0.0565(8) Uani 1 1 d . . .
H2 H 0.1914 0.6355 0.0269 0.068 Uiso 1 1 calc R . .
C3 C 0.4224(4) 0.65741(14) 0.0006(2) 0.0554(7) Uani 1 1 d . . .
H3 H 0.3845 0.6609 -0.0768 0.066 Uiso 1 1 calc R . .
C3A C 0.6041(4) 0.66978(13) 0.05493(18) 0.0450(6) Uani 1 1 d . . .
C4 C 0.7620(4) 0.67288(14) 0.0272(2) 0.0524(7) Uani 1 1 d . . .
H4 H 0.7778 0.6705 -0.0459 0.063 Uiso 1 1 calc R . .
O5 O 0.8967(2) 0.67983(10) 0.11794(13) 0.0538(5) Uani 1 1 d . . .
C5A C 0.8162(3) 0.68046(13) 0.20544(18) 0.0419(6) Uani 1 1 d . . .
C6 C 0.9071(3) 0.68032(14) 0.31919(19) 0.0449(6) Uani 1 1 d . . .
C6A C 0.7851(3) 0.67015(12) 0.39534(17) 0.0358(5) Uani 1 1 d . . .
C6B C 0.8563(3) 0.66500(12) 0.50889(18) 0.0384(6) Uani 1 1 d . . .
C7 C 1.0461(3) 0.66880(16) 0.5699(2) 0.0548(7) Uani 1 1 d . . .
H7X H 1.0977 0.7104 0.5580 0.066 Uiso 1 1 calc R . .
H7Y H 1.1166 0.6348 0.5459 0.066 Uiso 1 1 calc R . .
C8 C 1.0387(4) 0.66022(17) 0.6911(2) 0.0600(8) Uani 1 1 d . . .
H8X H 1.1056 0.6221 0.7219 0.072 Uiso 1 1 calc R . .
H8Y H 1.0898 0.6976 0.7345 0.072 Uiso 1 1 calc R . .
C9 C 0.8491(3) 0.65303(12) 0.69446(19) 0.0439(6) Uani 1 1 d . . .
C9A C 0.7463(3) 0.65590(11) 0.58033(17) 0.0368(5) Uani 1 1 d . . .
C10 C 0.5658(3) 0.65188(12) 0.54458(18) 0.0389(6) Uani 1 1 d . . .
H10 H 0.4928 0.6453 0.5952 0.047 Uiso 1 1 calc R . .
C11 C 0.4947(3) 0.65765(12) 0.43422(18) 0.0372(5) Uani 1 1 d . . .
H11 H 0.3709 0.6561 0.4088 0.045 Uiso 1 1 calc R . .
C11A C 0.6009(3) 0.66572(11) 0.35874(17) 0.0330(5) Uani 1 1 d . . .
C11B C 0.5107(3) 0.67669(12) 0.23906(17) 0.0365(5) Uani 1 1 d . . .
C11C C 0.6431(3) 0.67559(12) 0.17090(17) 0.0381(5) Uani 1 1 d . . .
Si12 Si 0.38783(16) 0.54231(5) 0.20913(7) 0.0773(4) Uani 1 1 d . . .
C13A C 0.2117(9) 0.5024(2) 0.1082(3) 0.164(3) Uani 1 1 d . . .
H13X H 0.2109 0.5186 0.0345 0.245 Uiso 1 1 calc R . .
H13Y H 0.0980 0.5110 0.1263 0.245 Uiso 1 1 calc R . .
H13Z H 0.2330 0.4567 0.1103 0.245 Uiso 1 1 calc R . .
C14A C 0.3566(9) 0.5183(2) 0.3461(3) 0.158(3) Uani 1 1 d . . .
H14X H 0.4588 0.5314 0.4023 0.238 Uiso 1 1 calc R . .
H14Y H 0.3435 0.4722 0.3483 0.238 Uiso 1 1 calc R . .
H14Z H 0.2509 0.5386 0.3603 0.238 Uiso 1 1 calc R . .
C15 C 0.6011(7) 0.5178(2) 0.1935(5) 0.153(2) Uani 1 1 d . . .
H15X H 0.6255 0.5368 0.1268 0.230 Uiso 1 1 calc R . .
H15Y H 0.6043 0.4715 0.1879 0.230 Uiso 1 1 calc R . .
H15Z H 0.6899 0.5318 0.2572 0.230 Uiso 1 1 calc R . .
O16 O 1.0651(2) 0.68612(12) 0.35106(15) 0.0694(7) Uani 1 1 d . . .
O17 O 0.7900(3) 0.64712(10) 0.77593(13) 0.0557(5) Uani 1 1 d . . .
C18 C 0.4327(3) 0.74426(13) 0.2350(2) 0.0472(6) Uani 1 1 d . . .
H18X H 0.5266 0.7747 0.2633 0.071 Uiso 1 1 calc R . .
H18Y H 0.3447 0.7459 0.2801 0.071 Uiso 1 1 calc R . .
H18Z H 0.3773 0.7551 0.1590 0.071 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 109.7(2) . . ?
C2 C1 Si12 107.20(19) . . ?
C11B C1 Si12 120.00(18) . . ?
C3 C2 C1 125.2(3) . . ?
C2 C3 C3A 118.0(2) . . ?
C4 C3A C11C 104.7(2) . . ?
C4 C3A C3 137.6(2) . . ?
C11C C3A C3 117.4(2) . . ?
C3A C4 O5 111.7(2) . . ?
C5A O5 C4 104.85(19) . . ?
C11C C5A O5 110.5(2) . . ?
C11C C5A C6 124.4(2) . . ?
O5 C5A C6 124.8(2) . . ?
O16 C6 C5A 124.5(2) . . ?
O16 C6 C6A 123.0(2) . . ?
C5A C6 C6A 112.4(2) . . ?
C6B C6A C11A 118.0(2) . . ?
C6B C6A C6 118.9(2) . . ?
C11A C6A C6 123.09(19) . . ?
C9A C6B C6A 119.8(2) . . ?
C9A C6B C7 111.1(2) . . ?
C6A C6B C7 129.1(2) . . ?
C6B C7 C8 104.2(2) . . ?
C9 C8 C7 106.9(2) . . ?
O17 C9 C9A 126.1(2) . . ?
O17 C9 C8 126.4(2) . . ?
C9A C9 C8 107.5(2) . . ?
C10 C9A C6B 122.2(2) . . ?
C10 C9A C9 127.5(2) . . ?
C6B C9A C9 110.3(2) . . ?
C11 C10 C9A 118.5(2) . . ?
C10 C11 C11A 121.3(2) . . ?
C11 C11A C6A 120.1(2) . . ?
C11 C11A C11B 117.8(2) . . ?
C6A C11A C11B 121.73(19) . . ?
C11C C11B C11A 109.41(19) . . ?
C11C C11B C18 108.4(2) . . ?
C11A C11B C18 105.43(19) . . ?
C11C C11B C1 107.62(19) . . ?
C11A C11B C1 117.74(19) . . ?
C18 C11B C1 107.9(2) . . ?
C5A C11C C3A 108.3(2) . . ?
C5A C11C C11B 127.0(2) . . ?
C3A C11C C11B 124.7(2) . . ?
C15 Si12 C14A 109.6(3) . . ?
C15 Si12 C13A 111.3(3) . . ?
C14A Si12 C13A 106.1(2) . . ?
C15 Si12 C1 110.22(18) . . ?
C14A Si12 C1 112.19(18) . . ?
C13A Si12 C1 107.4(2) . . ?
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 1.522(3) . ?
C1 C11B 1.562(3) . ?
C1 Si12 1.887(3) . ?
C2 C3 1.330(4) . ?
C3 C3A 1.456(4) . ?
C3A C4 1.353(4) . ?
C3A C11C 1.420(3) . ?
C4 O5 1.375(3) . ?
O5 C5A 1.375(3) . ?
C5A C11C 1.330(3) . ?
C5A C6 1.443(3) . ?
C6 O16 1.217(3) . ?
C6 C6A 1.502(3) . ?
C6A C6B 1.410(3) . ?
C6A C11A 1.414(3) . ?
C6B C9A 1.381(3) . ?
C6B C7 1.513(3) . ?
C7 C8 1.539(3) . ?
C8 C9 1.498(4) . ?
C9 O17 1.213(3) . ?
C9 C9A 1.477(3) . ?
C9A C10 1.385(3) . ?
C10 C11 1.375(3) . ?
C11 C11A 1.396(3) . ?
C11A C11B 1.525(3) . ?
C11B C11C 1.476(3) . ?
C11B C18 1.547(3) . ?
Si12 C15 1.795(5) . ?
Si12 C14A 1.852(4) . ?
Si12 C13A 1.853(4) . ?
