#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023898.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_4023898
loop_
_publ_author_name
'Ryukichi Takagi'
'Yuta Inoue'
'Katsuo Ohkata'
_publ_contact_author_address
;
Department of Chemistry, Graduate School of Science, Hiroshima University
1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan
;
_publ_contact_author_email       ' rtakagi@hiroshima-u.ac.jp '
_publ_contact_author_fax         ' +81-82-424-0747 '
_publ_contact_author_name        ' Ryukichi Takagi '
_publ_contact_author_phone       ' +81-82-424-7434 '
_publ_section_title
;
 Construction of the Adamantane Core of Plukenetione-Type
 Polycyclic Polyprenylated Acylphloroglucinols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9320
_journal_page_last               9325
_journal_paper_doi               10.1021/jo801595y
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C17 H30 O3 '
_chemical_formula_sum            'C17 H30 O3'
_chemical_formula_weight         282.42
_chemical_melting_point          117.5(15)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             'Thu Oct 19 16:11:14 2006'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 103.948(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.9040(6)
_cell_length_b                   8.0610(2)
_cell_length_c                   15.3390(4)
_cell_measurement_temperature    273.2
_cell_volume                     3348.5(1)
_computing_cell_refinement       Scalepack
_computing_data_collection       Denzo
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9478
_diffrn_measured_fraction_theta_max 0.9478
_diffrn_measurement_device_type  MacScienceDIP2030
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4079
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       thin
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.433
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3571
_refine_ls_R_factor_gt           0.0784
_refine_ls_shift/su_max          0.1251
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.20000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3240
_reflns_number_gt                2944
_reflns_number_total             3813
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo801595y_si_001.cif
_cod_data_source_block           bicyclo-reduction
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '116-119' was changed to '117.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_formula_sum        'C17 H30 O3 '
_cod_database_code               4023898
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O(1) O 0.71562(7) 0.0242(2) 0.0910(2) 0.0773(7) Uani 1.00 d . . .
O(2) O 0.56241(6) 0.0345(2) 0.17985(10) 0.0491(4) Uani 1.00 d . . .
O(3) O 0.54465(6) -0.0816(2) -0.15071(9) 0.0592(5) Uani 1.00 d . . .
C(1) C 0.68598(9) -0.0592(3) 0.1356(2) 0.0593(7) Uani 1.00 d . . .
C(2) C 0.6972(1) -0.2001(4) 0.1810(2) 0.0732(9) Uani 1.00 d . . .
C(3) C 0.6600(1) -0.2920(3) 0.2190(2) 0.0735(8) Uani 1.00 d . . .
C(4) C 0.60742(10) -0.2308(3) 0.1789(1) 0.0519(6) Uani 1.00 d . . .
C(5) C 0.59297(9) -0.2787(3) 0.0780(1) 0.0503(6) Uani 1.00 d . . .
C(6) C 0.57458(7) -0.1387(2) 0.0105(1) 0.0396(5) Uani 1.00 d . . .
C(7) C 0.60649(8) 0.0220(3) 0.0268(1) 0.0442(5) Uani 1.00 d . . .
C(8) C 0.63759(8) 0.0360(3) 0.1262(2) 0.0457(6) Uani 1.00 d . . .
C(9) C 0.60991(9) -0.0424(3) 0.1912(1) 0.0474(6) Uani 1.00 d . . .
C(10) C 0.7599(1) -0.0522(4) 0.0811(3) 0.085(1) Uani 1.00 d . . .
C(11) C 0.7776(2) 0.0408(7) 0.0127(4) 0.136(2) Uani 1.00 d . . .
C(12) C 0.5712(1) -0.3087(4) 0.2279(2) 0.0805(10) Uani 1.00 d . . .
C(13) C 0.56648(8) -0.2089(3) -0.0867(1) 0.0503(6) Uani 1.00 d . . .
C(14) C 0.6147(1) -0.2536(4) -0.1111(2) 0.0759(9) Uani 1.00 d . . .
C(15) C 0.5321(1) -0.3582(4) -0.1025(2) 0.0708(8) Uani 1.00 d . . .
C(16) C 0.5751(1) 0.1765(3) -0.0041(2) 0.0662(8) Uani 1.00 d . . .
C(17) C 0.6513(1) 0.2145(3) 0.1562(2) 0.0647(8) Uani 1.00 d . . .
H(2) H 0.7300 -0.2452 0.1875 0.0841 Uiso 1.00 calc . . .
H(2O) H 0.5541 0.0675 0.2338 0.0803 Uiso 1.00 calc . . .
H(3A) H 0.6618 -0.4062 0.2066 0.0849 Uiso 1.00 calc . . .
H(3B) H 0.6675 -0.2750 0.2824 0.0849 Uiso 1.00 calc . . .
H(3O) H 0.5103 -0.0510 -0.1490 0.0803 Uiso 1.00 calc . . .
H(5A) H 0.6212 -0.3253 0.0636 0.0616 Uiso 1.00 calc . . .
H(5B) H 0.5675 -0.3597 0.0700 0.0616 Uiso 1.00 calc . . .
H(6) H 0.5427 -0.1081 0.0180 0.0455 Uiso 1.00 calc . . .
H(7) H 0.6299 0.0154 -0.0102 0.0547 Uiso 1.00 calc . . .
H(9) H 0.6283 -0.0201 0.2511 0.0539 Uiso 1.00 calc . . .
H(10A) H 0.7834 -0.0567 0.1413 0.0949 Uiso 1.00 calc . . .
H(10B) H 0.7533 -0.1689 0.0655 0.0949 Uiso 1.00 calc . . .
H(11A) H 0.8089 -0.0034 0.0058 0.1525 Uiso 1.00 calc . . .
H(11B) H 0.7551 0.0444 -0.0415 0.1525 Uiso 1.00 calc . . .
H(11C) H 0.7854 0.1558 0.0344 0.1525 Uiso 1.00 calc . . .
H(12A) H 0.5807 -0.2765 0.2906 0.0864 Uiso 1.00 calc . . .
H(12B) H 0.5388 -0.2716 0.2035 0.0864 Uiso 1.00 calc . . .
H(12C) H 0.5727 -0.4260 0.2250 0.0864 Uiso 1.00 calc . . .
H(14A) H 0.6315 -0.3405 -0.0734 0.0851 Uiso 1.00 calc . . .
H(14B) H 0.6081 -0.2921 -0.1724 0.0851 Uiso 1.00 calc . . .
H(14C) H 0.6354 -0.1594 -0.1053 0.0851 Uiso 1.00 calc . . .
H(15A) H 0.5003 -0.3304 -0.0941 0.0920 Uiso 1.00 calc . . .
H(15B) H 0.5279 -0.3998 -0.1627 0.0920 Uiso 1.00 calc . . .
H(15C) H 0.5452 -0.4474 -0.0620 0.0920 Uiso 1.00 calc . . .
H(16A) H 0.5943 0.2733 -0.0010 0.0817 Uiso 1.00 calc . . .
H(16B) H 0.5571 0.1615 -0.0670 0.0817 Uiso 1.00 calc . . .
H(16C) H 0.5510 0.1899 0.0298 0.0817 Uiso 1.00 calc . . .
H(17A) H 0.6694 0.2174 0.2182 0.0750 Uiso 1.00 calc . . .
H(17B) H 0.6709 0.2660 0.1211 0.0750 Uiso 1.00 calc . . .
H(17C) H 0.6219 0.2800 0.1514 0.0750 Uiso 1.00 calc . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) O(1) C(10) 119.1(2) . . . yes
O(1) C(1) C(2) 125.9(2) . . . yes
O(1) C(1) C(8) 109.4(2) . . . yes
C(2) C(1) C(8) 124.7(2) . . . yes
C(1) C(2) C(3) 121.8(2) . . . yes
C(2) C(3) C(4) 111.8(2) . . . yes
C(3) C(4) C(5) 108.3(2) . . . yes
C(3) C(4) C(9) 105.1(2) . . . yes
C(3) C(4) C(12) 110.7(2) . . . yes
C(5) C(4) C(9) 111.2(2) . . . yes
C(5) C(4) C(12) 110.1(2) . . . yes
C(9) C(4) C(12) 111.3(2) . . . yes
C(4) C(5) C(6) 117.1(2) . . . yes
C(5) C(6) C(7) 114.7(2) . . . yes
C(5) C(6) C(13) 109.1(2) . . . yes
C(7) C(6) C(13) 113.6(2) . . . yes
C(6) C(7) C(8) 112.2(2) . . . yes
C(6) C(7) C(16) 111.4(2) . . . yes
C(8) C(7) C(16) 112.5(2) . . . yes
C(1) C(8) C(7) 109.0(2) . . . yes
C(1) C(8) C(9) 107.6(2) . . . yes
C(1) C(8) C(17) 107.0(2) . . . yes
C(7) C(8) C(9) 110.8(2) . . . yes
C(7) C(8) C(17) 113.6(2) . . . yes
C(9) C(8) C(17) 108.6(2) . . . yes
O(2) C(9) C(4) 113.6(2) . . . yes
O(2) C(9) C(8) 109.7(2) . . . yes
C(4) C(9) C(8) 110.1(2) . . . yes
O(1) C(10) C(11) 107.8(3) . . . yes
O(3) C(13) C(6) 109.3(2) . . . yes
O(3) C(13) C(14) 104.6(2) . . . yes
O(3) C(13) C(15) 107.9(2) . . . yes
C(6) C(13) C(14) 112.8(2) . . . yes
C(6) C(13) C(15) 112.3(2) . . . yes
C(14) C(13) C(15) 109.5(2) . . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.370(3) . . yes
O(1) C(10) 1.421(3) . . yes
O(2) C(9) 1.436(3) . . yes
O(3) C(13) 1.449(3) . . yes
C(1) C(2) 1.329(4) . . yes
C(1) C(8) 1.530(3) . . yes
C(2) C(3) 1.503(5) . . yes
C(3) C(4) 1.530(4) . . yes
C(4) C(5) 1.551(3) . . yes
C(4) C(9) 1.530(3) . . yes
C(4) C(12) 1.531(4) . . yes
C(5) C(6) 1.534(3) . . yes
C(6) C(7) 1.557(3) . . yes
C(6) C(13) 1.559(3) . . yes
C(7) C(8) 1.566(3) . . yes
C(7) C(16) 1.531(3) . . yes
C(8) C(9) 1.537(3) . . yes
C(8) C(17) 1.531(3) . . yes
C(10) C(11) 1.468(6) . . yes
C(13) C(14) 1.525(3) . . yes
C(13) C(15) 1.521(4) . . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(2) O(3) 2.787(2) . 4_555 ?
O(2) O(3) 2.937(2) . 3_655 ?
O(3) O(3) 3.439(3) . 2_654 ?
O(3) C(9) 3.511(3) . 4_554 ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O(1) C(1) C(2) C(3) -173.0(3) . . . . yes
O(1) C(1) C(8) C(7) 70.4(2) . . . . yes
O(1) C(1) C(8) C(9) -169.4(2) . . . . yes
O(1) C(1) C(8) C(17) -52.9(3) . . . . yes
O(2) C(9) C(4) C(3) -164.4(2) . . . . yes
O(2) C(9) C(4) C(5) 78.6(2) . . . . yes
O(2) C(9) C(4) C(12) -44.6(3) . . . . yes
O(2) C(9) C(8) C(1) -175.6(2) . . . . yes
O(2) C(9) C(8) C(7) -56.6(2) . . . . yes
O(2) C(9) C(8) C(17) 68.9(2) . . . . yes
O(3) C(13) C(6) C(5) 174.6(2) . . . . yes
O(3) C(13) C(6) C(7) -56.1(2) . . . . yes
C(1) O(1) C(10) C(11) 165.6(4) . . . . yes
C(1) C(2) C(3) C(4) 14.8(4) . . . . yes
C(1) C(8) C(7) C(6) 85.6(2) . . . . yes
C(1) C(8) C(7) C(16) -147.9(2) . . . . yes
C(1) C(8) C(9) C(4) -49.8(2) . . . . yes
C(2) C(1) O(1) C(10) 8.5(5) . . . . yes
C(2) C(1) C(8) C(7) -110.2(3) . . . . yes
C(2) C(1) C(8) C(9) 10.0(3) . . . . yes
C(2) C(1) C(8) C(17) 126.5(3) . . . . yes
C(2) C(3) C(4) C(5) 67.1(3) . . . . yes
C(2) C(3) C(4) C(9) -51.9(3) . . . . yes
C(2) C(3) C(4) C(12) -172.1(2) . . . . yes
C(3) C(2) C(1) C(8) 7.7(4) . . . . yes
C(3) C(4) C(5) C(6) -126.1(2) . . . . yes
C(3) C(4) C(9) C(8) 72.0(2) . . . . yes
C(4) C(5) C(6) C(7) 46.3(3) . . . . yes
C(4) C(5) C(6) C(13) 175.1(2) . . . . yes
C(4) C(9) C(8) C(7) 69.2(2) . . . . yes
C(4) C(9) C(8) C(17) -165.3(2) . . . . yes
C(5) C(4) C(9) C(8) -44.9(3) . . . . yes
C(5) C(6) C(7) C(8) -22.2(2) . . . . yes
C(5) C(6) C(7) C(16) -149.4(2) . . . . yes
C(5) C(6) C(13) C(14) -69.5(3) . . . . yes
C(5) C(6) C(13) C(15) 54.8(2) . . . . yes
C(6) C(5) C(4) C(9) -11.1(3) . . . . yes
C(6) C(5) C(4) C(12) 112.8(2) . . . . yes
C(6) C(7) C(8) C(9) -32.6(2) . . . . yes
C(6) C(7) C(8) C(17) -155.2(2) . . . . yes
C(7) C(6) C(13) C(14) 59.9(3) . . . . yes
C(7) C(6) C(13) C(15) -175.8(2) . . . . yes
C(8) C(1) O(1) C(10) -172.1(2) . . . . yes
C(8) C(7) C(6) C(13) -148.6(2) . . . . yes
C(8) C(9) C(4) C(12) -168.1(2) . . . . yes
C(9) C(8) C(7) C(16) 94.0(2) . . . . yes
C(13) C(6) C(7) C(16) 84.2(2) . . . . yes
C(16) C(7) C(8) C(17) -28.6(2) . . . . yes
C(16) C(7) C(8) C(17) -28.6(2) . . . . yes
