#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/47/4024719.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_4024719
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_absolute_configuration ad
_chemical_formula_sum            'C23 H28 O4 Si'
_chemical_formula_weight         396.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1222(5)
_cell_length_b                   14.0046(8)
_cell_length_c                   16.0182(9)
_cell_measurement_reflns_used    5121
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.57
_cell_volume                     2046.4(2)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15182
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Polyhedron
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_coef       0.0030(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.664
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         5090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.664
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0674
_reflns_number_gt                4622
_reflns_number_total             5090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900922q_si_003.cif
_cod_data_source_block           rr1279m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_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      P2_12_12_1
_cod_database_code               4024719
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32411(16) 0.38318(11) 0.18027(9) 0.0303(4) Uani 1 1 d . . .
H1 H 0.3581 0.4508 0.1746 0.036 Uiso 1 1 calc R . .
C2 C 0.18077(18) 0.38227(12) 0.13445(10) 0.0403(4) Uani 1 1 d . . .
H2 H 0.1748 0.4160 0.0831 0.048 Uiso 1 1 calc R . .
C3 C 0.06233(18) 0.33754(12) 0.16109(10) 0.0418(4) Uani 1 1 d . . .
H3 H -0.0218 0.3393 0.1262 0.050 Uiso 1 1 calc R . .
C3A C 0.04946(17) 0.28422(12) 0.24175(10) 0.0374(4) Uani 1 1 d . . .
H3A H -0.0399 0.3066 0.2722 0.045 Uiso 1 1 calc R . .
C4 C 0.03865(18) 0.17585(13) 0.22751(11) 0.0435(4) Uani 1 1 d . . .
H4X H -0.0267 0.1461 0.2694 0.052 Uiso 1 1 calc R . .
H4Y H 0.0000 0.1619 0.1711 0.052 Uiso 1 1 calc R . .
O5 O 0.18528(12) 0.14089(8) 0.23613(7) 0.0377(3) Uani 1 1 d . . .
C5A C 0.24384(16) 0.19036(11) 0.30408(10) 0.0300(3) Uani 1 1 d . . .
C6 C 0.40918(16) 0.17998(11) 0.30701(10) 0.0311(4) Uani 1 1 d . . .
C6A C 0.49250(16) 0.26348(11) 0.33716(9) 0.0267(3) Uani 1 1 d . . .
C6B C 0.62874(16) 0.25066(11) 0.37688(9) 0.0286(3) Uani 1 1 d . . .
C7 C 0.70655(16) 0.15952(11) 0.40014(10) 0.0355(4) Uani 1 1 d . . .
H7X H 0.7393 0.1247 0.3497 0.043 Uiso 1 1 calc R . .
H7Y H 0.6418 0.1173 0.4333 0.043 Uiso 1 1 calc R . .
C8 C 0.83840(18) 0.19298(13) 0.45226(10) 0.0419(4) Uani 1 1 d . . .
H8X H 0.8248 0.1758 0.5117 0.050 Uiso 1 1 calc R . .
H8Y H 0.9299 0.1629 0.4318 0.050 Uiso 1 1 calc R . .
C9 C 0.84562(18) 0.30063(13) 0.44214(10) 0.0386(4) Uani 1 1 d . . .
C9A C 0.70965(16) 0.32981(11) 0.39955(9) 0.0322(4) Uani 1 1 d . . .
C10 C 0.66267(19) 0.42174(12) 0.38160(11) 0.0392(4) Uani 1 1 d . . .
H10 H 0.7218 0.4753 0.3953 0.047 Uiso 1 1 calc R . .
C11 C 0.52873(19) 0.43389(11) 0.34348(10) 0.0359(4) Uani 1 1 d . . .
H11 H 0.4952 0.4967 0.3317 0.043 Uiso 1 1 calc R . .
C11A C 0.44079(17) 0.35586(10) 0.32161(9) 0.0276(3) Uani 1 1 d . . .
C11B C 0.29523(16) 0.37208(11) 0.27651(9) 0.0287(3) Uani 1 1 d . . .
C11C C 0.18452(16) 0.29290(11) 0.30010(9) 0.0299(4) Uani 1 1 d . . .
H11C H 0.1465 0.3087 0.3570 0.036 Uiso 1 1 calc R . .
Si12 Si 0.45905(5) 0.31300(3) 0.11207(3) 0.03347(12) Uani 1 1 d . . .
C13 C 0.39548(19) 0.19243(12) 0.08067(11) 0.0462(5) Uani 1 1 d . . .
H13X H 0.4668 0.1639 0.0423 0.069 Uiso 1 1 calc R . .
H13Y H 0.3002 0.1976 0.0528 0.069 Uiso 1 1 calc R . .
H13Z H 0.3858 0.1520 0.1303 0.069 Uiso 1 1 calc R . .
C14 C 0.64837(18) 0.30261(15) 0.15525(11) 0.0487(5) Uani 1 1 d . . .
H14X H 0.7179 0.2925 0.1095 0.073 Uiso 1 1 calc R . .
H14Y H 0.6529 0.2484 0.1939 0.073 Uiso 1 1 calc R . .
H14Z H 0.6737 0.3615 0.1851 0.073 Uiso 1 1 calc R . .
C15 C 0.4704(2) 0.38632(13) 0.01450(10) 0.0482(5) Uani 1 1 d . . .
H15X H 0.4889 0.4532 0.0292 0.072 Uiso 1 1 calc R . .
H15Y H 0.3777 0.3816 -0.0161 0.072 Uiso 1 1 calc R . .
H15Z H 0.5505 0.3625 -0.0206 0.072 Uiso 1 1 calc R . .
O16 O 0.19007(11) 0.15306(7) 0.38166(7) 0.0347(3) Uani 1 1 d . . .
C17 C 0.2027(2) 0.05126(11) 0.39033(12) 0.0481(5) Uani 1 1 d . . .
H17X H 0.1703 0.0203 0.3387 0.072 Uiso 1 1 calc R . .
H17Y H 0.1412 0.0297 0.4368 0.072 Uiso 1 1 calc R . .
H17Z H 0.3051 0.0344 0.4014 0.072 Uiso 1 1 calc R . .
O18 O 0.46831(13) 0.10476(8) 0.28887(8) 0.0467(3) Uani 1 1 d . . .
O19 O 0.94500(14) 0.35232(9) 0.46483(7) 0.0526(3) Uani 1 1 d . . .
C20 C 0.22275(19) 0.46584(12) 0.30713(11) 0.0415(4) Uani 1 1 d . . .
H20X H 0.2154 0.4649 0.3682 0.062 Uiso 1 1 calc R . .
H20Y H 0.1245 0.4715 0.2829 0.062 Uiso 1 1 calc R . .
H20Z H 0.2825 0.5204 0.2897 0.062 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 109.45(13) . . ?
C2 C1 Si12 106.06(11) . . ?
C11B C1 Si12 128.02(11) . . ?
C3 C2 C1 124.03(15) . . ?
C2 C3 C3A 125.45(15) . . ?
C3 C3A C4 111.67(14) . . ?
C3 C3A C11C 114.75(13) . . ?
C4 C3A C11C 102.57(13) . . ?
O5 C4 C3A 105.27(12) . . ?
C5A O5 C4 105.25(12) . . ?
O5 C5A O16 111.34(11) . . ?
O5 C5A C6 110.93(13) . . ?
O16 C5A C6 106.16(13) . . ?
O5 C5A C11C 107.26(13) . . ?
O16 C5A C11C 104.83(12) . . ?
C6 C5A C11C 116.20(13) . . ?
O18 C6 C6A 122.35(14) . . ?
O18 C6 C5A 121.05(14) . . ?
C6A C6 C5A 116.52(13) . . ?
C11A C6A C6B 119.74(13) . . ?
C11A C6A C6 120.04(13) . . ?
C6B C6A C6 120.10(14) . . ?
C9A C6B C6A 119.24(14) . . ?
C9A C6B C7 111.29(13) . . ?
C6A C6B C7 129.46(14) . . ?
C6B C7 C8 104.16(13) . . ?
C9 C8 C7 106.18(13) . . ?
O19 C9 C9A 126.94(17) . . ?
O19 C9 C8 126.29(16) . . ?
C9A C9 C8 106.77(14) . . ?
C6B C9A C10 121.71(14) . . ?
C6B C9A C9 110.44(14) . . ?
C10 C9A C9 127.85(15) . . ?
C11 C10 C9A 118.75(15) . . ?
C10 C11 C11A 121.54(15) . . ?
C6A C11A C11 118.94(14) . . ?
C6A C11A C11B 120.96(13) . . ?
C11 C11A C11B 120.00(14) . . ?
C11A C11B C11C 110.19(12) . . ?
C11A C11B C20 110.30(13) . . ?
C11C C11B C20 104.57(12) . . ?
C11A C11B C1 109.43(12) . . ?
C11C C11B C1 114.83(13) . . ?
C20 C11B C1 107.35(12) . . ?
C5A C11C C11B 116.77(12) . . ?
C5A C11C C3A 103.39(12) . . ?
C11B C11C C3A 115.31(12) . . ?
C13 Si12 C14 108.59(9) . . ?
C13 Si12 C15 106.86(8) . . ?
C14 Si12 C15 107.51(8) . . ?
C13 Si12 C1 114.87(8) . . ?
C14 Si12 C1 115.03(8) . . ?
C15 Si12 C1 103.29(8) . . ?
C5A O16 C17 114.68(13) . . ?
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 1.500(2) . ?
C1 C11B 1.572(2) . ?
C1 Si12 1.9169(15) . ?
C2 C3 1.320(2) . ?
C3 C3A 1.497(2) . ?
C3A C4 1.538(2) . ?
C3A C11C 1.551(2) . ?
C4 O5 1.4311(19) . ?
O5 C5A 1.3964(17) . ?
C5A O16 1.4346(18) . ?
C5A C6 1.516(2) . ?
C5A C11C 1.536(2) . ?
C6 O18 1.2186(17) . ?
C6 C6A 1.476(2) . ?
C6A C11A 1.399(2) . ?
C6A C6B 1.408(2) . ?
C6B C9A 1.380(2) . ?
C6B C7 1.507(2) . ?
C7 C8 1.537(2) . ?
C8 C9 1.518(2) . ?
C9 O19 1.2157(19) . ?
C9 C9A 1.473(2) . ?
C9A C10 1.387(2) . ?
C10 C11 1.377(2) . ?
C11 C11A 1.400(2) . ?
C11A C11B 1.529(2) . ?
C11B C11C 1.547(2) . ?
C11B C20 1.550(2) . ?
Si12 C13 1.8549(18) . ?
Si12 C14 1.8660(17) . ?
Si12 C15 1.8729(17) . ?
O16 C17 1.4371(18) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659009
