#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:03:23 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180329 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/43/7154396.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_7154396
loop_
_publ_author_name
'Hsu, Che-Sheng'
'Chou, Ho-Hsuan'
'Fang, Jim-Min'
_publ_section_title
;
 A short synthesis of (+-)-antroquinonol in an unusual scaffold of
 4-hydroxy-2-cyclohexenone.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5510
_journal_page_last               5519
_journal_paper_doi               10.1039/c5ob00411j
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.305(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8399(6)
_cell_length_b                   5.2999(3)
_cell_length_c                   28.5110(16)
_cell_measurement_reflns_used    1802
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      74.5300
_cell_measurement_theta_min      4.5690
_cell_volume                     1471.27(15)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4894
_diffrn_reflns_theta_full        67.96
_diffrn_reflns_theta_max         67.96
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.101
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1651
_reflns_number_gt                1946
_reflns_number_total             2684
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00411j2.cif
_cod_data_source_block           ic16451
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 3143 2015-03-26 13:38:13Z robertas 

 Adding full bibliography for 7154396--7154401.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7154396
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.49681(17) 0.9650(3) 0.07880(6) 0.0721(5) Uani 1 1 d .
H1A H 0.4687 0.9847 0.0505 0.108 Uiso 1 1 calc R
O2 O 0.63652(17) 0.8151(4) 0.01016(6) 0.0813(6) Uani 1 1 d .
O3 O 0.85785(14) 0.4964(3) 0.02290(5) 0.0626(4) Uani 1 1 d .
O4 O 0.89665(15) 0.2317(3) 0.11192(6) 0.0671(5) Uani 1 1 d .
C1 C 0.5684(2) 0.7338(4) 0.08544(7) 0.0496(5) Uani 1 1 d .
H1B H 0.5014 0.5959 0.0831 0.059 Uiso 1 1 calc R
C2 C 0.6595(2) 0.6976(4) 0.04746(7) 0.0536(5) Uani 1 1 d .
C3 C 0.7720(2) 0.5225(4) 0.05711(7) 0.0498(5) Uani 1 1 d .
C4 C 0.80007(19) 0.4099(4) 0.09937(7) 0.0487(5) Uani 1 1 d .
C5 C 0.7272(2) 0.4738(4) 0.14132(7) 0.0522(5) Uani 1 1 d .
H5A H 0.6576 0.3436 0.1434 0.063 Uiso 1 1 calc R
C6 C 0.65319(19) 0.7276(4) 0.13444(7) 0.0476(5) Uani 1 1 d .
H6A H 0.7243 0.8574 0.1348 0.057 Uiso 1 1 calc R
C7 C 0.5664(2) 0.7985(4) 0.17337(7) 0.0562(5) Uani 1 1 d .
H7A H 0.6271 0.8079 0.2033 0.067 Uiso 1 1 calc R
H7B H 0.5288 0.9658 0.1665 0.067 Uiso 1 1 calc R
C8 C 0.4496(2) 0.6229(4) 0.17947(7) 0.0516(5) Uani 1 1 d .
C9 C 0.4631(3) 0.4387(5) 0.21407(9) 0.0678(6) Uani 1 1 d .
H9A H 0.5459 0.4219 0.2342 0.081 Uiso 1 1 calc R
C10 C 0.3541(3) 0.2770(5) 0.21934(10) 0.0812(8) Uani 1 1 d .
H10A H 0.3647 0.1527 0.2426 0.097 Uiso 1 1 calc R
C11 C 0.2321(3) 0.3023(5) 0.19017(11) 0.0812(8) Uani 1 1 d .
H11A H 0.1597 0.1941 0.1934 0.097 Uiso 1 1 calc R
C12 C 0.2159(3) 0.4864(6) 0.15609(10) 0.0778(8) Uani 1 1 d .
H12A H 0.1323 0.5039 0.1365 0.093 Uiso 1 1 calc R
C13 C 0.3237(2) 0.6460(5) 0.15085(8) 0.0631(6) Uani 1 1 d .
H13A H 0.3116 0.7711 0.1277 0.076 Uiso 1 1 calc R
C14 C 0.7972(3) 0.3882(6) -0.02116(9) 0.0840(8) Uani 1 1 d .
H14A H 0.8646 0.3790 -0.0423 0.126 Uiso 1 1 calc R
H14B H 0.7218 0.4915 -0.0350 0.126 Uiso 1 1 calc R
H14C H 0.7644 0.2217 -0.0157 0.126 Uiso 1 1 calc R
C15 C 0.9613(3) 0.0939(5) 0.07765(10) 0.0787(7) Uani 1 1 d .
H15A H 1.0258 -0.0242 0.0937 0.118 Uiso 1 1 calc R
H15B H 1.0085 0.2095 0.0597 0.118 Uiso 1 1 calc R
H15C H 0.8927 0.0046 0.0567 0.118 Uiso 1 1 calc R
C16 C 0.8277(3) 0.4674(7) 0.18757(9) 0.0941(10) Uani 1 1 d .
H16A H 0.8720 0.3056 0.1909 0.141 Uiso 1 1 calc R
H16B H 0.7786 0.4956 0.2138 0.141 Uiso 1 1 calc R
H16C H 0.8957 0.5969 0.1869 0.141 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
C3 O3 C14 116.00(16)
C4 O4 C15 122.54(19)
O1 C1 C2 110.45(16)
O1 C1 C6 109.80(17)
C2 C1 C6 110.59(15)
O2 C2 C3 122.26(19)
O2 C2 C1 120.15(19)
C3 C2 C1 117.58(17)
C4 C3 O3 121.45(18)
C4 C3 C2 120.85(18)
O3 C3 C2 117.36(18)
C3 C4 O4 126.62(19)
C3 C4 C5 123.39(18)
O4 C4 C5 109.97(17)
C4 C5 C6 111.44(16)
C4 C5 C16 110.68(17)
C6 C5 C16 111.5(2)
C1 C6 C7 111.66(15)
C1 C6 C5 108.94(16)
C7 C6 C5 115.15(17)
C8 C7 C6 116.32(16)
C13 C8 C9 117.9(2)
C13 C8 C7 120.57(19)
C9 C8 C7 121.5(2)
C8 C9 C10 121.0(3)
C11 C10 C9 119.7(2)
C10 C11 C12 120.3(2)
C13 C12 C11 120.0(3)
C12 C13 C8 121.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.413(2)
O2 C2 1.225(3)
O3 C3 1.386(2)
O3 C14 1.431(3)
O4 C4 1.351(2)
O4 C15 1.439(3)
C1 C2 1.514(3)
C1 C6 1.520(3)
C2 C3 1.440(3)
C3 C4 1.337(3)
C4 C5 1.519(3)
C5 C6 1.528(3)
C5 C16 1.530(3)
C6 C7 1.541(3)
C7 C8 1.508(3)
C8 C13 1.387(3)
C8 C9 1.381(3)
C9 C10 1.398(4)
C10 C11 1.365(4)
C11 C12 1.370(4)
C12 C13 1.381(3)
