#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:57:15 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180324 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/38/7153840.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_7153840
loop_
_publ_author_name
'Ruiz, Jérémy'
'Mallet-Ladeira, Sonia'
'Maynadier, Marjorie'
'Vial, Henri'
'André-Barrès, Christiane'
_publ_section_title
;
 Design, synthesis and evaluation of new tricyclic endoperoxides as
 potential antiplasmodial agents.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5212
_journal_page_last               5221
_journal_paper_doi               10.1039/c4ob00787e
_journal_volume                  12
_journal_year                    2014
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H16 O4'
_chemical_formula_sum            'C12 H16 O4'
_chemical_formula_weight         224.25
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                110.196(4)
_cell_angle_beta                 95.635(4)
_cell_angle_gamma                101.286(4)
_cell_formula_units_Z            2
_cell_length_a                   6.4719(5)
_cell_length_b                   8.7411(6)
_cell_length_c                   10.9321(8)
_cell_measurement_reflns_used    4870
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      31.07
_cell_measurement_theta_min      2.56
_cell_measurement_wavelength     0.71073
_cell_volume                     559.89(7)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10737
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.1860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                2198
_reflns_number_total             2765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00787e2.cif
_cod_data_source_block           11cis
_cod_depositor_comments
'Adding full bibliography for 7153840--7153841.cif.'
_cod_database_code               7153840
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
O2 O 0.38090(13) 0.08129(11) 0.15323(9) 0.0285(2) Uani 1 1 d .
H2 H 0.2896 -0.0112 0.1172 0.043 Uiso 1 1 calc R
O1 O -0.10520(15) 0.23706(11) -0.01853(9) 0.0284(2) Uani 1 1 d .
O3 O 0.27318(14) 0.18586(11) 0.35765(9) 0.0275(2) Uani 1 1 d .
O4 O 0.11931(14) 0.02434(11) 0.32983(9) 0.0279(2) Uani 1 1 d .
C5 C 0.28596(19) 0.20143(15) 0.23224(12) 0.0222(2) Uani 1 1 d .
C4 C 0.4348(2) 0.37554(15) 0.26458(13) 0.0258(3) Uani 1 1 d .
H4 H 0.5817 0.3834 0.3084 0.031 Uiso 1 1 calc R
C9 C -0.11029(19) 0.11601(15) 0.19771(12) 0.0217(2) Uani 1 1 d .
H9 H -0.2476 0.1084 0.1529 0.026 Uiso 1 1 calc R
C6 C 0.06376(18) 0.18761(14) 0.16359(11) 0.0195(2) Uani 1 1 d .
C8 C 0.4404(2) 0.40352(16) 0.13376(14) 0.0298(3) Uani 1 1 d .
H8A H 0.4554 0.3021 0.062 0.036 Uiso 1 1 calc R
H8B H 0.5584 0.5004 0.1435 0.036 Uiso 1 1 calc R
C1 C 0.2202(2) 0.43935(15) 0.10797(13) 0.0270(3) Uani 1 1 d .
H1 H 0.2115 0.4903 0.0392 0.032 Uiso 1 1 calc R
C10 C -0.09452(19) 0.04688(16) 0.30556(12) 0.0242(3) Uani 1 1 d .
C3 C 0.3423(2) 0.51902(16) 0.34785(13) 0.0317(3) Uani 1 1 d .
H3A H 0.459 0.6179 0.4037 0.038 Uiso 1 1 calc R
H3B H 0.2533 0.4821 0.4059 0.038 Uiso 1 1 calc R
C7 C 0.04597(19) 0.28011(14) 0.07242(12) 0.0214(2) Uani 1 1 d .
C2 C 0.2043(2) 0.56281(16) 0.24654(14) 0.0323(3) Uani 1 1 d .
H2A H 0.2604 0.6808 0.2558 0.039 Uiso 1 1 calc R
H2B H 0.0537 0.5473 0.26 0.039 Uiso 1 1 calc R
C12 C -0.1516(2) 0.16352(19) 0.43054(14) 0.0351(3) Uani 1 1 d .
H12A H -0.1427 0.1164 0.4997 0.053 Uiso 1 1 calc R
H12B H -0.2976 0.1747 0.4108 0.053 Uiso 1 1 calc R
H12C H -0.0511 0.2744 0.4614 0.053 Uiso 1 1 calc R
C11 C -0.2345(2) -0.13181(18) 0.26151(15) 0.0341(3) Uani 1 1 d .
H11A H -0.185 -0.2065 0.1868 0.051 Uiso 1 1 calc R
H11B H -0.3836 -0.1327 0.2341 0.051 Uiso 1 1 calc R
H11C H -0.2246 -0.1709 0.3353 0.051 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C5 O2 H2 109.5
C5 O3 O4 106.33(8)
C10 O4 O3 108.05(8)
O2 C5 O3 111.24(10)
O2 C5 C6 111.39(9)
O3 C5 C6 109.47(9)
O2 C5 C4 107.73(10)
O3 C5 C4 105.36(9)
C6 C5 C4 111.49(10)
C8 C4 C5 107.29(10)
C8 C4 C3 103.25(11)
C5 C4 C3 112.34(11)
C8 C4 H4 111.2
C5 C4 H4 111.2
C3 C4 H4 111.2
C6 C9 C10 121.42(11)
C6 C9 H9 119.3
C10 C9 H9 119.3
C9 C6 C7 120.55(10)
C9 C6 C5 120.89(10)
C7 C6 C5 117.87(10)
C4 C8 C1 101.59(10)
C4 C8 H8A 111.5
C1 C8 H8A 111.5
C4 C8 H8B 111.5
C1 C8 H8B 111.5
H8A C8 H8B 109.3
C7 C1 C8 109.67(10)
C7 C1 C2 108.05(10)
C8 C1 C2 102.45(10)
C7 C1 H1 112.1
C8 C1 H1 112.1
C2 C1 H1 112.1
O4 C10 C9 109.14(9)
O4 C10 C12 111.70(10)
C9 C10 C12 110.22(10)
O4 C10 C11 102.70(10)
C9 C10 C11 111.81(10)
C12 C10 C11 111.08(11)
C4 C3 C2 105.66(11)
C4 C3 H3A 110.6
C2 C3 H3A 110.6
C4 C3 H3B 110.6
C2 C3 H3B 110.6
H3A C3 H3B 108.7
O1 C7 C6 122.72(11)
O1 C7 C1 122.33(11)
C6 C7 C1 114.77(10)
C3 C2 C1 105.46(11)
C3 C2 H2A 110.6
C1 C2 H2A 110.6
C3 C2 H2B 110.6
C1 C2 H2B 110.6
H2A C2 H2B 108.8
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C5 1.3989(15)
O2 H2 0.84
O1 C7 1.2222(15)
O3 C5 1.4324(14)
O3 O4 1.4735(12)
O4 C10 1.4474(15)
C5 C6 1.5177(16)
C5 C4 1.5354(16)
C4 C8 1.5344(18)
C4 C3 1.5403(19)
C4 H4 1
C9 C6 1.3295(16)
C9 C10 1.5028(16)
C9 H9 0.95
C6 C7 1.4935(16)
C8 C1 1.5375(19)
C8 H8A 0.99
C8 H8B 0.99
C1 C7 1.5121(16)
C1 C2 1.5541(19)
C1 H1 1
C10 C12 1.5254(19)
C10 C11 1.5274(17)
C3 C2 1.5501(19)
C3 H3A 0.99
C3 H3B 0.99
C2 H2A 0.99
C2 H2B 0.99
C12 H12A 0.98
C12 H12B 0.98
C12 H12C 0.98
C11 H11A 0.98
C11 H11B 0.98
C11 H11C 0.98
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84 1.96 2.7941(12) 172.2 2
