#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/28/1502804.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_1502804
loop_
_publ_author_name
'Chokpaiboon, Supichar'
'Sommit, Damrong'
'Teerawatananond, Thapong'
'Muangsin, Nongnuj'
'Bunyapaiboonsri, Taridaporn'
'Pudhom, Khanitha'
_publ_section_title
;
 Cytotoxic nor-chamigrane and chamigrane endoperoxides from a
 basidiomycetous fungus.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1005
_journal_page_last               1007
_journal_paper_doi               10.1021/np100103j
_journal_volume                  73
_journal_year                    2010
_chemical_formula_sum            'C17 H30 O4'
_chemical_formula_weight         298.41
_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
_audit_update_record
;
2010-01-13 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.35260(10)
_cell_length_b                   12.4749(3)
_cell_length_c                   13.9626(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.25
_cell_measurement_theta_min      2.19
_cell_volume                     1280.69(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'APEX II'
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15534
_diffrn_reflns_theta_full        33.25
_diffrn_reflns_theta_max         33.25
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_correction_T_min  0.9726
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4861
_refine_ls_number_restraints     174
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0422
_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)+(0.0739P)²+0.1030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                4207
_reflns_number_total             4861
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np100103j_si_001.cif
_cod_data_source_block           522111_1_0m
_cod_database_code               1502804
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.48794(15) 0.29457(8) 0.18513(7) 0.02891(18) Uani 1 1 d U
H1A H 0.5510 0.2331 0.2117 0.035 Uiso 1 1 calc R
H1B H 0.3589 0.2859 0.1974 0.035 Uiso 1 1 calc R
C2 C 0.52103(15) 0.30012(8) 0.07823(7) 0.02979(19) Uani 1 1 d U
H2 H 0.4768 0.2328 0.0506 0.036 Uiso 1 1 calc R
C3 C 0.41115(18) 0.39061(9) 0.03329(7) 0.0334(2) Uani 1 1 d U
H3 H 0.2821 0.3720 0.0391 0.040 Uiso 1 1 calc R
C4 C 0.4393(2) 0.49824(9) 0.08227(9) 0.0414(3) Uani 1 1 d U
H4A H 0.3431 0.5468 0.0627 0.050 Uiso 1 1 calc R
H4B H 0.5540 0.5285 0.0612 0.050 Uiso 1 1 calc R
C5 C 0.44001(17) 0.48990(9) 0.19221(8) 0.0353(2) Uani 1 1 d U
H5A H 0.3157 0.4805 0.2139 0.042 Uiso 1 1 calc R
H5B H 0.4839 0.5572 0.2183 0.042 Uiso 1 1 calc R
C6 C 0.55681(13) 0.39792(7) 0.23367(6) 0.02292(15) Uani 1 1 d U
C7 C 0.76191(14) 0.41036(9) 0.20393(7) 0.02897(19) Uani 1 1 d U
C8 C 0.88151(16) 0.32610(11) 0.25294(9) 0.0384(2) Uani 1 1 d U
C9 C 0.86165(19) 0.32098(13) 0.35991(9) 0.0478(3) Uani 1 1 d U
H9A H 0.9066 0.3869 0.3882 0.057 Uiso 1 1 calc R
H9B H 0.9336 0.2620 0.3848 0.057 Uiso 1 1 calc R
C10 C 0.66285(19) 0.30514(11) 0.38713(9) 0.0410(3) Uani 1 1 d U
H10A H 0.6530 0.3059 0.4564 0.049 Uiso 1 1 calc R
H10B H 0.6242 0.2350 0.3652 0.049 Uiso 1 1 calc R
C11 C 0.53253(14) 0.38960(9) 0.34610(7) 0.02939(19) Uani 1 1 d U
C12 C 0.5600(2) 0.49656(11) 0.39869(9) 0.0447(3) Uani 1 1 d U
H12A H 0.4784 0.5493 0.3729 0.067 Uiso 1 1 calc R
H12B H 0.6832 0.5202 0.3904 0.067 Uiso 1 1 calc R
H12C H 0.5355 0.4870 0.4657 0.067 Uiso 1 1 calc R
C13 C 0.33899(19) 0.35238(14) 0.37226(10) 0.0505(3) Uani 1 1 d U
H13A H 0.3137 0.2854 0.3411 0.076 Uiso 1 1 calc R
H13B H 0.2526 0.4052 0.3516 0.076 Uiso 1 1 calc R
H13C H 0.3301 0.3433 0.4404 0.076 Uiso 1 1 calc R
C14 C 0.8507(2) 0.52059(12) 0.22106(11) 0.0493(3) Uani 1 1 d U
H14A H 0.7788 0.5753 0.1910 0.074 Uiso 1 1 calc R
H14B H 0.9709 0.5209 0.1942 0.074 Uiso 1 1 calc R
H14C H 0.8578 0.5342 0.2886 0.074 Uiso 1 1 calc R
O1 O 0.98656(15) 0.27035(11) 0.20889(9) 0.0633(4) Uani 1 1 d U
O2 O 0.44985(17) 0.40432(8) -0.06559(6) 0.0484(2) Uani 1 1 d U
H2O H 0.4356 0.3472 -0.0936 0.073 Uiso 1 1 calc R
O3 O 0.71217(13) 0.30474(8) 0.06124(6) 0.0404(2) Uani 1 1 d U
O4 O 0.78256(13) 0.40466(8) 0.10154(6) 0.0399(2) Uani 1 1 d U
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
C2 C1 C6 110.02(8)
O3 C2 C1 108.92(8)
O3 C2 C3 115.09(10)
C1 C2 C3 110.78(9)
O2 C3 C4 107.67(10)
O2 C3 C2 112.55(10)
C4 C3 C2 113.39(9)
C3 C4 C5 112.92(9)
C4 C5 C6 115.20(9)
C1 C6 C5 105.88(8)
C1 C6 C7 106.35(8)
C5 C6 C7 111.15(9)
C1 C6 C11 110.11(8)
C5 C6 C11 110.94(8)
C7 C6 C11 112.12(7)
O4 C7 C8 110.44(9)
O4 C7 C14 98.84(9)
C8 C7 C14 107.44(10)
O4 C7 C6 111.02(8)
C8 C7 C6 111.41(9)
C14 C7 C6 116.98(10)
O1 C8 C9 122.96(13)
O1 C8 C7 122.34(12)
C9 C8 C7 114.68(10)
C8 C9 C10 110.30(11)
C9 C10 C11 114.63(10)
C10 C11 C12 109.61(10)
C10 C11 C13 106.33(10)
C12 C11 C13 105.65(10)
C10 C11 C6 110.16(8)
C12 C11 C6 113.71(9)
C13 C11 C6 111.04(9)
C2 O3 O4 108.61(8)
C7 O4 O3 112.77(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5139(14)
C1 C6 1.5421(13)
C2 O3 1.4265(14)
C2 C3 1.5235(15)
C3 O2 1.4201(14)
C3 C4 1.5208(15)
C4 C5 1.5385(16)
C5 C6 1.5457(13)
C6 C7 1.5718(14)
C6 C11 1.5834(13)
C7 O4 1.4393(12)
C7 C8 1.5318(16)
C7 C14 1.5410(16)
C8 O1 1.2077(16)
C8 C9 1.5021(17)
C9 C10 1.523(2)
C10 C11 1.5351(17)
C11 C12 1.5364(16)
C11 C13 1.5408(17)
O3 O4 1.4622(13)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 29214914 ChemSpider
