#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/78/1517847.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_1517847
loop_
_publ_author_name
'Peng, Xing-Rong'
'Liu, Jie-Qing'
'Wan, Luo-Sheng'
'Li, Xiao-Nian'
'Yan, Yu-Xin'
'Qiu, Ming-Hua'
_publ_section_title
;
 Four New Polycyclic Meroterpenoids from Ganoderma cochlear.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5262
_journal_page_last               5265
_journal_paper_doi               10.1021/ol5023189
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C23 H26 O5'
_chemical_formula_sum            'C23 H26 O5'
_chemical_formula_weight         382.44
_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                 99.334(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5635(6)
_cell_length_b                   21.3915(9)
_cell_length_c                   7.2398(4)
_cell_measurement_reflns_used    3074
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.54
_cell_measurement_theta_min      4.12
_cell_volume                     1919.95(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2693
_diffrn_reflns_av_sigmaI/netI    0.1400
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            17282
_diffrn_reflns_theta_full        70.01
_diffrn_reflns_theta_max         70.01
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.7738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       piece
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.852
_refine_diff_density_min         -2.357
_refine_diff_density_rms         0.314
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.729
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     168
_refine_ls_restrained_S_all      1.718
_refine_ls_R_factor_all          0.2671
_refine_ls_R_factor_gt           0.1731
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3829
_refine_ls_wR_factor_ref         0.4830
_reflns_number_gt                2124
_reflns_number_total             3539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5023189_si_002.cif
_cod_data_source_block           cu_kfbb181_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517847.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1517847
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
O4 O 0.3617(4) 0.1861(2) 0.1716(6) 0.0107(11) Uani 1 1 d U
O15' O 0.9758(4) 0.2342(3) 0.7316(8) 0.0219(13) Uani 1 1 d U
O7 O 0.2804(4) 0.1694(2) -0.1271(7) 0.0175(12) Uani 1 1 d U
O1 O 0.7769(4) 0.1512(2) 0.0335(6) 0.0092(11) Uani 1 1 d U
O1' O 0.6753(4) 0.0442(2) 0.4500(6) 0.0092(11) Uani 1 1 d U
C8 C 0.1754(6) 0.2029(3) 0.1029(11) 0.0190(16) Uani 1 1 d U
H8A H 0.1160 0.2075 -0.0022 0.028 Uiso 1 1 calc R
H8B H 0.1877 0.2429 0.1690 0.028 Uiso 1 1 calc R
H8C H 0.1568 0.1709 0.1891 0.028 Uiso 1 1 calc R
C7 C 0.2744(6) 0.1841(3) 0.0314(10) 0.0126(15) Uani 1 1 d U
C4 C 0.4651(5) 0.1767(3) 0.1256(9) 0.0098(14) Uani 1 1 d U
C3 C 0.5319(5) 0.1368(3) 0.2441(9) 0.0091(14) Uani 1 1 d U
H3 H 0.5057 0.1154 0.3426 0.011 Uiso 1 1 calc R
C2 C 0.6391(5) 0.1287(3) 0.2149(10) 0.0089(14) Uani 1 1 d U
C1' C 0.7216(5) 0.0930(3) 0.3558(9) 0.0083(14) Uani 1 1 d U
C2' C 0.7597(5) 0.1428(3) 0.4985(9) 0.0078(14) Uani 1 1 d U
H2' H 0.7077 0.1608 0.5643 0.009 Uiso 1 1 calc R
C3' C 0.8614(5) 0.1637(3) 0.5396(10) 0.0105(15) Uani 1 1 d U
C15' C 0.8848(6) 0.2147(3) 0.6756(10) 0.0120(15) Uani 1 1 d U
H15' H 0.8262 0.2335 0.7227 0.014 Uiso 1 1 calc R
C1 C 0.6738(5) 0.1595(3) 0.0691(9) 0.0090(14) Uani 1 1 d U
C6 C 0.6079(5) 0.2016(3) -0.0439(10) 0.0097(14) Uani 1 1 d U
H6 H 0.6348 0.2244 -0.1392 0.012 Uiso 1 1 calc R
C5 C 0.5020(6) 0.2097(3) -0.0146(10) 0.0144(15) Uani 1 1 d U
H5 H 0.4555 0.2379 -0.0908 0.017 Uiso 1 1 calc R
C7' C 0.8124(5) 0.0863(3) 0.0600(10) 0.0110(14) Uani 1 1 d U
C8' C 0.7342(6) 0.0419(3) -0.0651(10) 0.0114(14) Uani 1 1 d U
H8'1 H 0.6585 0.0555 -0.0703 0.014 Uiso 1 1 calc R
H8'2 H 0.7511 0.0405 -0.1940 0.014 Uiso 1 1 calc R
C9' C 0.7532(6) -0.0213(3) 0.0297(10) 0.0133(15) Uani 1 1 d U
H9'1 H 0.8156 -0.0427 -0.0100 0.016 Uiso 1 1 calc R
H9'2 H 0.6887 -0.0483 -0.0013 0.016 Uiso 1 1 calc R
C10' C 0.7756(5) -0.0070(3) 0.2400(10) 0.0108(15) Uani 1 1 d U
H10' H 0.8374 -0.0337 0.2976 0.013 Uiso 1 1 calc R
C11' C 0.6822(5) -0.0159(3) 0.3569(10) 0.0103(15) Uani 1 1 d U
C13' C 0.7116(6) -0.0635(3) 0.5105(11) 0.0187(17) Uani 1 1 d U
H13A H 0.7834 -0.0540 0.5800 0.028 Uiso 1 1 calc R
H13B H 0.7121 -0.1053 0.4555 0.028 Uiso 1 1 calc R
H13C H 0.6585 -0.0621 0.5958 0.028 Uiso 1 1 calc R
C4' C 0.9512(6) 0.1338(3) 0.4590(10) 0.0113(15) Uani 1 1 d U
H4'1 H 1.0173 0.1329 0.5542 0.014 Uiso 1 1 calc R
H4'2 H 0.9666 0.1586 0.3508 0.014 Uiso 1 1 calc R
C5' C 0.9197(6) 0.0678(3) 0.3964(10) 0.0121(15) Uani 1 1 d U
H5'1 H 0.9160 0.0420 0.5088 0.015 Uiso 1 1 calc R
H5'2 H 0.9773 0.0502 0.3335 0.015 Uiso 1 1 calc R
C6' C 0.8122(5) 0.0623(3) 0.2637(10) 0.0094(14) Uani 1 1 d U
C12' C 0.5726(6) -0.0309(3) 0.2432(11) 0.0165(16) Uani 1 1 d U
H12A H 0.5177 -0.0300 0.3250 0.025 Uiso 1 1 calc R
H12B H 0.5745 -0.0725 0.1876 0.025 Uiso 1 1 calc R
H12C H 0.5549 0.0002 0.1436 0.025 Uiso 1 1 calc R
C14' C 0.9229(6) 0.0857(3) 0.0001(10) 0.0147(16) Uani 1 1 d U
H14A H 0.9165 0.1002 -0.1296 0.022 Uiso 1 1 calc R
H14B H 0.9518 0.0430 0.0094 0.022 Uiso 1 1 calc R
H14C H 0.9718 0.1134 0.0819 0.022 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C7 O4 C4 118.6(5)
C1 O1 C7' 112.1(5)
C1' O1' C11' 111.4(5)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O7 C7 O4 123.3(6)
O7 C7 C8 126.2(7)
O4 C7 C8 110.5(6)
C5 C4 C3 121.9(6)
C5 C4 O4 122.3(6)
C3 C4 O4 115.5(6)
C4 C3 C2 118.6(6)
C4 C3 H3 120.7
C2 C3 H3 120.7
C1 C2 C3 119.2(6)
C1 C2 C1' 119.0(6)
C3 C2 C1' 121.4(6)
O1' C1' C2' 107.4(5)
O1' C1' C2 113.5(5)
C2' C1' C2 102.0(5)
O1' C1' C6' 106.4(5)
C2' C1' C6' 114.8(5)
C2 C1' C6' 112.8(5)
C3' C2' C1' 124.9(6)
C3' C2' H2' 117.5
C1' C2' H2' 117.5
C2' C3' C15' 118.5(6)
C2' C3' C4' 121.6(6)
C15' C3' C4' 119.9(6)
O15' C15' C3' 123.5(7)
O15' C15' H15' 118.3
C3' C15' H15' 118.3
O1 C1 C2 120.6(6)
O1 C1 C6 117.6(6)
C2 C1 C6 121.8(6)
C5 C6 C1 118.9(6)
C5 C6 H6 120.6
C1 C6 H6 120.6
C4 C5 C6 119.5(7)
C4 C5 H5 120.3
C6 C5 H5 120.3
O1 C7' C14' 104.2(5)
O1 C7' C8' 110.7(5)
C14' C7' C8' 110.5(5)
O1 C7' C6' 112.9(5)
C14' C7' C6' 114.1(6)
C8' C7' C6' 104.6(5)
C9' C8' C7' 104.1(5)
C9' C8' H8'1 110.9
C7' C8' H8'1 110.9
C9' C8' H8'2 110.9
C7' C8' H8'2 110.9
H8'1 C8' H8'2 109.0
C8' C9' C10' 105.1(6)
C8' C9' H9'1 110.7
C10' C9' H9'1 110.7
C8' C9' H9'2 110.7
C10' C9' H9'2 110.7
H9'1 C9' H9'2 108.8
C9' C10' C6' 107.7(5)
C9' C10' C11' 118.6(6)
C6' C10' C11' 107.0(5)
C9' C10' H10' 107.7
C6' C10' H10' 107.7
C11' C10' H10' 107.7
O1' C11' C13' 106.2(5)
O1' C11' C12' 108.6(5)
C13' C11' C12' 110.5(6)
O1' C11' C10' 104.3(5)
C13' C11' C10' 111.4(6)
C12' C11' C10' 115.2(6)
C11' C13' H13A 109.5
C11' C13' H13B 109.5
H13A C13' H13B 109.5
C11' C13' H13C 109.5
H13A C13' H13C 109.5
H13B C13' H13C 109.5
C3' C4' C5' 109.8(6)
C3' C4' H4'1 109.7
C5' C4' H4'1 109.7
C3' C4' H4'2 109.7
C5' C4' H4'2 109.7
H4'1 C4' H4'2 108.2
C4' C5' C6' 114.8(6)
C4' C5' H5'1 108.6
C6' C5' H5'1 108.6
C4' C5' H5'2 108.6
C6' C5' H5'2 108.6
H5'1 C5' H5'2 107.5
C5' C6' C10' 111.0(5)
C5' C6' C1' 109.4(5)
C10' C6' C1' 103.0(5)
C5' C6' C7' 115.6(6)
C10' C6' C7' 104.8(5)
C1' C6' C7' 112.3(5)
C11' C12' H12A 109.5
C11' C12' H12B 109.5
H12A C12' H12B 109.5
C11' C12' H12C 109.5
H12A C12' H12C 109.5
H12B C12' H12C 109.5
C7' C14' H14A 109.5
C7' C14' H14B 109.5
H14A C14' H14B 109.5
C7' C14' H14C 109.5
H14A C14' H14C 109.5
H14B C14' H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C7 1.369(9)
O4 C4 1.407(8)
O15' C15' 1.222(9)
O7 C7 1.203(9)
O1 C1 1.373(8)
O1 C7' 1.461(8)
O1' C1' 1.422(7)
O1' C11' 1.461(8)
C8 C7 1.479(10)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C4 C5 1.377(10)
C4 C3 1.391(9)
C3 C2 1.407(9)
C3 H3 0.9500
C2 C1 1.374(9)
C2 C1' 1.535(9)
C1' C2' 1.508(9)
C1' C6' 1.554(9)
C2' C3' 1.341(9)
C2' H2' 0.9500
C3' C15' 1.467(9)
C3' C4' 1.494(9)
C15' H15' 0.9500
C1 C6 1.395(9)
C6 C5 1.391(9)
C6 H6 0.9500
C5 H5 0.9500
C7' C14' 1.520(9)
C7' C8' 1.549(9)
C7' C6' 1.562(9)
C8' C9' 1.518(9)
C8' H8'1 0.9900
C8' H8'2 0.9900
C9' C10' 1.534(10)
C9' H9'1 0.9900
C9' H9'2 0.9900
C10' C6' 1.553(9)
C10' C11' 1.566(9)
C10' H10' 1.0000
C11' C13' 1.509(10)
C11' C12' 1.519(10)
C13' H13A 0.9800
C13' H13B 0.9800
C13' H13C 0.9800
C4' C5' 1.516(9)
C4' H4'1 0.9900
C4' H4'2 0.9900
C5' C6' 1.530(10)
C5' H5'1 0.9900
C5' H5'2 0.9900
C12' H12A 0.9800
C12' H12B 0.9800
C12' H12C 0.9800
C14' H14A 0.9800
C14' H14B 0.9800
C14' H14C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 O4 C7 O7 6.5(9)
C4 O4 C7 C8 -172.8(5)
C7 O4 C4 C5 51.5(9)
C7 O4 C4 C3 -135.2(6)
C5 C4 C3 C2 -2.1(10)
O4 C4 C3 C2 -175.4(6)
C4 C3 C2 C1 -1.1(10)
C4 C3 C2 C1' 171.3(6)
C11' O1' C1' C2' -153.3(5)
C11' O1' C1' C2 94.7(6)
C11' O1' C1' C6' -29.9(7)
C1 C2 C1' O1' -156.0(6)
C3 C2 C1' O1' 31.7(8)
C1 C2 C1' C2' 88.7(7)
C3 C2 C1' C2' -83.6(7)
C1 C2 C1' C6' -34.9(8)
C3 C2 C1' C6' 152.8(6)
O1' C1' C2' C3' 122.1(7)
C2 C1' C2' C3' -118.2(7)
C6' C1' C2' C3' 4.1(9)
C1' C2' C3' C15' 177.0(6)
C1' C2' C3' C4' -6.5(11)
C2' C3' C15' O15' 175.1(7)
C4' C3' C15' O15' -1.4(11)
C7' O1 C1 C2 39.0(8)
C7' O1 C1 C6 -143.0(6)
C3 C2 C1 O1 -178.0(6)
C1' C2 C1 O1 9.5(10)
C3 C2 C1 C6 4.0(10)
C1' C2 C1 C6 -168.5(6)
O1 C1 C6 C5 178.2(6)
C2 C1 C6 C5 -3.8(10)
C3 C4 C5 C6 2.3(11)
O4 C4 C5 C6 175.2(6)
C1 C6 C5 C4 0.6(10)
C1 O1 C7' C14' 175.8(5)
C1 O1 C7' C8' 57.0(7)
C1 O1 C7' C6' -60.0(7)
O1 C7' C8' C9' -158.1(5)
C14' C7' C8' C9' 87.0(6)
C6' C7' C8' C9' -36.2(6)
C7' C8' C9' C10' 35.3(7)
C8' C9' C10' C6' -21.2(7)
C8' C9' C10' C11' 100.4(7)
C1' O1' C11' C13' 139.1(6)
C1' O1' C11' C12' -102.0(6)
C1' O1' C11' C10' 21.3(7)
C9' C10' C11' O1' -126.1(6)
C6' C10' C11' O1' -4.2(7)
C9' C10' C11' C13' 119.7(7)
C6' C10' C11' C13' -118.4(6)
C9' C10' C11' C12' -7.1(9)
C6' C10' C11' C12' 114.8(6)
C2' C3' C4' C5' -21.5(9)
C15' C3' C4' C5' 154.9(6)
C3' C4' C5' C6' 53.4(8)
C4' C5' C6' C10' -168.4(6)
C4' C5' C6' C1' -55.4(7)
C4' C5' C6' C7' 72.6(7)
C9' C10' C6' C5' -126.7(6)
C11' C10' C6' C5' 104.8(6)
C9' C10' C6' C1' 116.4(6)
C11' C10' C6' C1' -12.2(7)
C9' C10' C6' C7' -1.3(7)
C11' C10' C6' C7' -129.8(6)
O1' C1' C6' C5' -93.2(6)
C2' C1' C6' C5' 25.5(7)
C2 C1' C6' C5' 141.7(6)
O1' C1' C6' C10' 24.9(6)
C2' C1' C6' C10' 143.5(6)
C2 C1' C6' C10' -100.2(6)
O1' C1' C6' C7' 137.1(5)
C2' C1' C6' C7' -104.3(6)
C2 C1' C6' C7' 12.0(8)
O1 C7' C6' C5' -94.3(7)
C14' C7' C6' C5' 24.4(8)
C8' C7' C6' C5' 145.2(6)
O1 C7' C6' C10' 143.3(5)
C14' C7' C6' C10' -98.1(6)
C8' C7' C6' C10' 22.8(7)
O1 C7' C6' C1' 32.2(8)
C14' C7' C6' C1' 150.8(6)
C8' C7' C6' C1' -88.3(6)
