#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024725.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_4024725
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            'C19 H12 O5'
_chemical_formula_weight         320.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.303(6)
_cell_angle_beta                 92.306(6)
_cell_angle_gamma                101.349(5)
_cell_formula_units_Z            2
_cell_length_a                   7.7207(18)
_cell_length_b                   9.454(2)
_cell_length_c                   10.226(2)
_cell_measurement_reflns_used    1746
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.29
_cell_volume                     702.5(3)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4314
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Needle fragment'
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0309(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.390
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.390
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0583
_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)+(0.0010P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0719
_reflns_number_gt                1789
_reflns_number_total             2795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900922q_si_009.cif
_cod_data_source_block           rr1340m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               4024725
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.1348(3) 0.4213(3) 0.1175(2) 0.0460(6) Uani 1 1 d . . .
H1 H 0.0272 0.4583 0.1419 0.055 Uiso 1 1 calc R . .
C2 C 0.1053(3) 0.2653(3) 0.0267(2) 0.0522(7) Uani 1 1 d . . .
H2 H -0.0185 0.2121 -0.0012 0.063 Uiso 1 1 calc R . .
C3 C 0.2395(3) 0.1699(3) 0.0242(3) 0.0535(7) Uani 1 1 d . . .
C3A C 0.4108(3) 0.2530(3) 0.0910(2) 0.0469(6) Uani 1 1 d . . .
C4 C 0.5781(3) 0.2239(3) 0.0808(3) 0.0559(7) Uani 1 1 d . . .
H4 H 0.6040 0.1342 0.0311 0.067 Uiso 1 1 calc R . .
O5 O 0.6997(2) 0.3461(2) 0.15448(19) 0.0633(5) Uani 1 1 d . . .
C5A C 0.6069(3) 0.4560(3) 0.2108(3) 0.0519(7) Uani 1 1 d . . .
C6 C 0.6852(3) 0.6076(3) 0.2820(2) 0.0485(7) Uani 1 1 d . . .
C6A C 0.5544(3) 0.7090(3) 0.2860(2) 0.0419(6) Uani 1 1 d . . .
C6B C 0.6182(3) 0.8653(3) 0.3217(2) 0.0448(6) Uani 1 1 d . . .
C7 C 0.8065(3) 0.9546(3) 0.3648(3) 0.0602(8) Uani 1 1 d . . .
H7X H 0.8849 0.9222 0.2966 0.072 Uiso 1 1 calc R . .
H7Y H 0.8503 0.9433 0.4509 0.072 Uiso 1 1 calc R . .
C8 C 0.7937(3) 1.1186(3) 0.3787(3) 0.0687(8) Uani 1 1 d . . .
H8X H 0.8516 1.1836 0.4657 0.082 Uiso 1 1 calc R . .
H8Y H 0.8499 1.1537 0.3065 0.082 Uiso 1 1 calc R . .
C9 C 0.5976(4) 1.1186(3) 0.3683(2) 0.0559(7) Uani 1 1 d . . .
C9A C 0.5020(3) 0.9594(3) 0.3222(2) 0.0458(6) Uani 1 1 d . . .
C10 C 0.3217(3) 0.9042(3) 0.2881(2) 0.0517(7) Uani 1 1 d . . .
H10 H 0.2453 0.9689 0.2880 0.062 Uiso 1 1 calc R . .
C11 C 0.2575(3) 0.7508(3) 0.2543(2) 0.0484(7) Uani 1 1 d . . .
H11 H 0.1361 0.7124 0.2329 0.058 Uiso 1 1 calc R . .
C11A C 0.3707(3) 0.6526(2) 0.2517(2) 0.0398(6) Uani 1 1 d . . .
C11B C 0.2932(3) 0.4847(2) 0.2227(2) 0.0392(6) Uani 1 1 d . . .
C11C C 0.4336(3) 0.4017(3) 0.1760(2) 0.0426(6) Uani 1 1 d . . .
O12 O 0.1665(2) 0.39559(19) -0.02273(17) 0.0617(5) Uani 1 1 d . . .
O13 O 0.1998(2) 0.0352(2) -0.0331(2) 0.0767(6) Uani 1 1 d . . .
O14 O 0.8399(2) 0.6546(2) 0.32933(17) 0.0686(6) Uani 1 1 d . . .
O15 O 0.5311(3) 1.2268(2) 0.39373(18) 0.0764(6) Uani 1 1 d . . .
C16 C 0.2292(3) 0.4536(3) 0.3563(2) 0.0578(7) Uani 1 1 d . . .
H16X H 0.1951 0.3472 0.3434 0.087 Uiso 1 1 calc R . .
H16Y H 0.1292 0.4982 0.3799 0.087 Uiso 1 1 calc R . .
H16Z H 0.3236 0.4962 0.4284 0.087 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
O12 C1 C2 59.74(14) . . ?
O12 C1 C11B 117.75(18) . . ?
C2 C1 C11B 121.1(2) . . ?
O12 C2 C1 58.08(14) . . ?
O12 C2 C3 113.4(2) . . ?
C1 C2 C3 122.1(2) . . ?
O13 C3 C3A 126.1(2) . . ?
O13 C3 C2 120.4(3) . . ?
C3A C3 C2 113.5(2) . . ?
C4 C3A C11C 106.1(2) . . ?
C4 C3A C3 132.4(2) . . ?
C11C C3A C3 121.1(2) . . ?
O5 C4 C3A 109.6(2) . . ?
C4 O5 C5A 106.98(19) . . ?
C11C C5A O5 109.5(2) . . ?
C11C C5A C6 124.9(2) . . ?
O5 C5A C6 125.3(2) . . ?
O14 C6 C5A 125.4(2) . . ?
O14 C6 C6A 123.0(2) . . ?
C5A C6 C6A 111.5(2) . . ?
C6B C6A C11A 118.2(2) . . ?
C6B C6A C6 119.2(2) . . ?
C11A C6A C6 122.6(2) . . ?
C9A C6B C6A 120.2(2) . . ?
C9A C6B C7 110.9(2) . . ?
C6A C6B C7 129.0(2) . . ?
C6B C7 C8 104.5(2) . . ?
C9 C8 C7 106.1(2) . . ?
O15 C9 C9A 126.3(3) . . ?
O15 C9 C8 126.9(3) . . ?
C9A C9 C8 106.8(2) . . ?
C6B C9A C10 121.7(2) . . ?
C6B C9A C9 110.6(2) . . ?
C10 C9A C9 127.6(2) . . ?
C11 C10 C9A 118.6(2) . . ?
C10 C11 C11A 121.3(2) . . ?
C11 C11A C6A 120.1(2) . . ?
C11 C11A C11B 119.6(2) . . ?
C6A C11A C11B 120.1(2) . . ?
C11C C11B C1 107.60(18) . . ?
C11C C11B C11A 108.68(18) . . ?
C1 C11B C11A 116.05(18) . . ?
C11C C11B C16 110.22(18) . . ?
C1 C11B C16 105.88(17) . . ?
C11A C11B C16 108.34(18) . . ?
C5A C11C C3A 107.8(2) . . ?
C5A C11C C11B 124.7(2) . . ?
C3A C11C C11B 127.5(2) . . ?
C1 O12 C2 62.18(14) . . ?
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 O12 1.429(3) . ?
C1 C2 1.489(3) . ?
C1 C11B 1.509(3) . ?
C2 O12 1.454(3) . ?
C2 C3 1.499(3) . ?
C3 O13 1.223(3) . ?
C3 C3A 1.438(3) . ?
C3A C4 1.375(3) . ?
C3A C11C 1.417(3) . ?
C4 O5 1.356(3) . ?
O5 C5A 1.391(3) . ?
C5A C11C 1.333(3) . ?
C5A C6 1.422(3) . ?
C6 O14 1.220(2) . ?
C6 C6A 1.518(3) . ?
C6A C6B 1.404(3) . ?
C6A C11A 1.408(3) . ?
C6B C9A 1.382(3) . ?
C6B C7 1.513(3) . ?
C7 C8 1.543(3) . ?
C8 C9 1.514(3) . ?
C9 O15 1.207(3) . ?
C9 C9A 1.480(3) . ?
C9A C10 1.383(3) . ?
C10 C11 1.380(3) . ?
C11 C11A 1.391(3) . ?
C11A C11B 1.526(3) . ?
C11B C11C 1.482(3) . ?
C11B C16 1.551(3) . ?
