#------------------------------------------------------------------------------
#$Date: 2017-02-04 04:16:50 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191356 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/48/1544815.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_1544815
loop_
_publ_author_name
'Luo, Qi'
'Wei, Xiao-Yi'
'Yang, Jing'
'Luo, Jin-Feng'
'Liang, Rui'
'Tu, Zheng-Chao'
'Cheng, Yong-Xian'
_publ_section_title
;
 Spiro Meroterpenoids from Ganoderma applanatum.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              61
_journal_page_last               70
_journal_paper_doi               10.1021/acs.jnatprod.6b00431
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H18 O6'
_chemical_formula_sum            'C17 H18 O6'
_chemical_formula_weight         318.31
_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                   6.10060(10)
_cell_length_b                   15.0443(2)
_cell_length_c                   16.0425(2)
_cell_measurement_reflns_used    9051
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.14
_cell_measurement_theta_min      5.52
_cell_volume                     1472.37(4)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9165
_diffrn_reflns_theta_full        69.53
_diffrn_reflns_theta_max         69.53
_diffrn_reflns_theta_min         5.51
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.8383
_exptl_absorpt_correction_T_min  0.6333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(13)
_refine_ls_extinction_coef       0.0126(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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0274
_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)+(0.0381P)²+0.3873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                2679
_reflns_number_total             2682
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np6b00431_si_002.cif
_cod_data_source_block           cu_qpg39_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1544815.cif.
;
_cod_database_code               1544815
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
O11' O 0.37823(16) 0.27859(6) 0.62833(6) 0.0203(2) Uani 1 1 d .
O4 O -0.43515(17) 0.61767(7) 0.37151(6) 0.0232(2) Uani 1 1 d .
H4 H -0.4112 0.6582 0.3367 0.035 Uiso 1 1 calc R
O1 O 0.25114(15) 0.57634(6) 0.58922(6) 0.0166(2) Uani 1 1 d .
O1' O -0.11755(15) 0.39542(6) 0.61075(6) 0.0170(2) Uani 1 1 d .
O9' O 0.09731(17) 0.77660(6) 0.75990(6) 0.0211(2) Uani 1 1 d .
H9' H 0.1148 0.8061 0.8038 0.032 Uiso 1 1 calc R
O10' O 0.34163(17) 0.36381(6) 0.51435(6) 0.0224(2) Uani 1 1 d .
C11' C 0.3556(3) 0.19958(9) 0.57722(9) 0.0242(3) Uani 1 1 d .
H11A H 0.2189 0.2030 0.5453 0.036 Uiso 1 1 calc R
H11B H 0.3525 0.1469 0.6131 0.036 Uiso 1 1 calc R
H11C H 0.4800 0.1955 0.5388 0.036 Uiso 1 1 calc R
C10' C 0.3637(2) 0.35592(9) 0.58862(8) 0.0172(3) Uani 1 1 d .
C3' C 0.3763(2) 0.43427(9) 0.64764(8) 0.0165(3) Uani 1 1 d .
H3' H 0.5117 0.4680 0.6324 0.020 Uiso 1 1 calc R
C2' C 0.1820(2) 0.49968(8) 0.63747(8) 0.0152(3) Uani 1 1 d .
C1' C -0.0202(2) 0.46393(8) 0.59201(8) 0.0153(3) Uani 1 1 d .
C2 C -0.0723(2) 0.52827(8) 0.52832(8) 0.0162(3) Uani 1 1 d .
C3 C -0.2505(2) 0.53543(9) 0.47387(8) 0.0171(3) Uani 1 1 d .
H3 H -0.3625 0.4916 0.4727 0.021 Uiso 1 1 calc R
C4 C -0.2579(2) 0.60830(8) 0.42190(8) 0.0174(3) Uani 1 1 d .
C5 C -0.0859(2) 0.67084(8) 0.42282(8) 0.0177(3) Uani 1 1 d .
H5 H -0.0925 0.7198 0.3856 0.021 Uiso 1 1 calc R
C6 C 0.0924(2) 0.66370(9) 0.47589(8) 0.0170(3) Uani 1 1 d .
H6 H 0.2081 0.7059 0.4752 0.020 Uiso 1 1 calc R
C1 C 0.0937(2) 0.59162(8) 0.53038(8) 0.0154(3) Uani 1 1 d .
C4' C 0.3925(2) 0.41475(9) 0.74124(8) 0.0190(3) Uani 1 1 d .
H4'1 H 0.2947 0.3651 0.7573 0.023 Uiso 1 1 calc R
H4'2 H 0.5448 0.3998 0.7574 0.023 Uiso 1 1 calc R
C5' C 0.3190(2) 0.50164(9) 0.78134(8) 0.0184(3) Uani 1 1 d .
H5'1 H 0.4348 0.5476 0.7775 0.022 Uiso 1 1 calc R
H5'2 H 0.2791 0.4928 0.8406 0.022 Uiso 1 1 calc R
C6' C 0.1176(2) 0.52705(8) 0.72888(8) 0.0164(3) Uani 1 1 d .
H6' H -0.0040 0.4866 0.7464 0.020 Uiso 1 1 calc R
C7' C 0.0299(2) 0.62100(9) 0.73507(8) 0.0175(3) Uani 1 1 d .
C9' C 0.1821(2) 0.68945(8) 0.77135(9) 0.0189(3) Uani 1 1 d .
H9'1 H 0.2020 0.6779 0.8316 0.023 Uiso 1 1 calc R
H9'2 H 0.3272 0.6848 0.7441 0.023 Uiso 1 1 calc R
C8' C -0.1706(2) 0.64178(10) 0.70936(10) 0.0234(3) Uani 1 1 d .
H8'1 H -0.2214 0.7013 0.7136 0.028 Uiso 1 1 calc R
H8'2 H -0.2632 0.5971 0.6867 0.028 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
C10' O11' C11' 116.10(10)
C4 O4 H4 109.5
C1 O1 C2' 107.31(10)
C9' O9' H9' 109.5
O11' C11' H11A 109.5
O11' C11' H11B 109.5
H11A C11' H11B 109.5
O11' C11' H11C 109.5
H11A C11' H11C 109.5
H11B C11' H11C 109.5
O10' C10' O11' 124.59(12)
O10' C10' C3' 123.18(12)
O11' C10' C3' 112.23(11)
C10' C3' C4' 117.81(11)
C10' C3' C2' 112.96(11)
C4' C3' C2' 105.92(10)
C10' C3' H3' 106.5
C4' C3' H3' 106.5
C2' C3' H3' 106.5
O1 C2' C1' 105.04(10)
O1 C2' C3' 109.77(10)
C1' C2' C3' 116.34(10)
O1 C2' C6' 111.20(10)
C1' C2' C6' 109.59(10)
C3' C2' C6' 105.01(10)
O1' C1' C2 129.08(12)
O1' C1' C2' 124.65(12)
C2 C1' C2' 106.22(11)
C1 C2 C3 121.86(12)
C1 C2 C1' 106.40(12)
C3 C2 C1' 131.70(12)
C4 C3 C2 117.71(12)
C4 C3 H3 121.1
C2 C3 H3 121.1
O4 C4 C3 117.99(12)
O4 C4 C5 122.01(12)
C3 C4 C5 120.00(12)
C6 C5 C4 122.63(12)
C6 C5 H5 118.7
C4 C5 H5 118.7
C5 C6 C1 116.78(12)
C5 C6 H6 121.6
C1 C6 H6 121.6
O1 C1 C2 114.40(11)
O1 C1 C6 124.65(12)
C2 C1 C6 120.95(12)
C5' C4' C3' 103.30(10)
C5' C4' H4'1 111.1
C3' C4' H4'1 111.1
C5' C4' H4'2 111.1
C3' C4' H4'2 111.1
H4'1 C4' H4'2 109.1
C4' C5' C6' 102.55(10)
C4' C5' H5'1 111.3
C6' C5' H5'1 111.3
C4' C5' H5'2 111.3
C6' C5' H5'2 111.3
H5'1 C5' H5'2 109.2
C7' C6' C5' 118.59(11)
C7' C6' C2' 113.18(10)
C5' C6' C2' 104.25(10)
C7' C6' H6' 106.7
C5' C6' H6' 106.7
C2' C6' H6' 106.7
C8' C7' C9' 121.85(13)
C8' C7' C6' 121.66(12)
C9' C7' C6' 116.49(11)
O9' C9' C7' 110.92(11)
O9' C9' H9'1 109.5
C7' C9' H9'1 109.5
O9' C9' H9'2 109.5
C7' C9' H9'2 109.5
H9'1 C9' H9'2 108.0
C7' C8' H8'1 120.0
C7' C8' H8'2 120.0
H8'1 C8' H8'2 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O11' C10' 1.3293(16)
O11' C11' 1.4506(16)
O4 C4 1.3572(16)
O4 H4 0.8400
O1 C1 1.3662(16)
O1 C2' 1.4517(15)
O1' C1' 1.2269(16)
O9' C9' 1.4213(16)
O9' H9' 0.8400
O10' C10' 1.2050(18)
C11' H11A 0.9800
C11' H11B 0.9800
C11' H11C 0.9800
C10' C3' 1.5139(18)
C3' C4' 1.5334(18)
C3' C2' 1.5492(17)
C3' H3' 1.0000
C2' C1' 1.5303(17)
C2' C6' 1.5729(17)
C1' C2 1.4430(18)
C2 C1 1.3910(18)
C2 C3 1.3984(19)
C3 C4 1.3780(19)
C3 H3 0.9500
C4 C5 1.4096(19)
C5 C6 1.385(2)
C5 H5 0.9500
C6 C1 1.3930(18)
C6 H6 0.9500
C4' C5' 1.5244(18)
C4' H4'1 0.9900
C4' H4'2 0.9900
C5' C6' 1.5373(18)
C5' H5'1 0.9900
C5' H5'2 0.9900
C6' C7' 1.5148(18)
C6' H6' 1.0000
C7' C8' 1.328(2)
C7' C9' 1.5038(19)
C9' H9'1 0.9900
C9' H9'2 0.9900
C8' H8'1 0.9500
C8' H8'2 0.9500
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
O4 H4 O9' 0.84 1.83 2.6485(13) 162.8 2_466
O9' H9' O1' 0.84 1.92 2.7417(12) 166.1 3_556
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
C11' O11' C10' O10' -2.8(2)
C11' O11' C10' C3' 176.72(11)
O10' C10' C3' C4' 176.88(13)
O11' C10' C3' C4' -2.66(16)
O10' C10' C3' C2' 52.82(17)
O11' C10' C3' C2' -126.73(12)
C1 O1 C2' C1' 7.58(12)
C1 O1 C2' C3' 133.37(10)
C1 O1 C2' C6' -110.87(11)
C10' C3' C2' O1 -101.18(12)
C4' C3' C2' O1 128.46(11)
C10' C3' C2' C1' 17.87(15)
C4' C3' C2' C1' -112.49(12)
C10' C3' C2' C6' 139.20(11)
C4' C3' C2' C6' 8.84(13)
O1 C2' C1' O1' 174.83(11)
C3' C2' C1' O1' 53.24(16)
C6' C2' C1' O1' -65.63(15)
O1 C2' C1' C2 -7.73(12)
C3' C2' C1' C2 -129.32(12)
C6' C2' C1' C2 111.80(11)
O1' C1' C2 C1 -177.73(13)
C2' C1' C2 C1 4.99(13)
O1' C1' C2 C3 4.6(2)
C2' C1' C2 C3 -172.66(13)
C1 C2 C3 C4 -0.40(18)
C1' C2 C3 C4 176.94(13)
C2 C3 C4 O4 -177.17(11)
C2 C3 C4 C5 2.16(19)
O4 C4 C5 C6 177.79(12)
C3 C4 C5 C6 -1.5(2)
C4 C5 C6 C1 -0.98(19)
C2' O1 C1 C2 -4.92(14)
C2' O1 C1 C6 174.91(12)
C3 C2 C1 O1 177.70(11)
C1' C2 C1 O1 -0.23(14)
C3 C2 C1 C6 -2.14(19)
C1' C2 C1 C6 179.93(11)
C5 C6 C1 O1 -177.07(11)
C5 C6 C1 C2 2.75(18)
C10' C3' C4' C5' -160.12(11)
C2' C3' C4' C5' -32.60(13)
C3' C4' C5' C6' 43.82(12)
C4' C5' C6' C7' -165.01(11)
C4' C5' C6' C2' -38.07(12)
O1 C2' C6' C7' 29.50(15)
C1' C2' C6' C7' -86.18(13)
C3' C2' C6' C7' 148.17(11)
O1 C2' C6' C5' -100.73(11)
C1' C2' C6' C5' 143.59(11)
C3' C2' C6' C5' 17.93(12)
C5' C6' C7' C8' -162.61(13)
C2' C6' C7' C8' 74.82(16)
C5' C6' C7' C9' 17.74(17)
C2' C6' C7' C9' -104.82(13)
C8' C7' C9' O9' -10.27(19)
C6' C7' C9' O9' 169.37(11)
