#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:45:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180314 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/28/7152842.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_7152842
loop_
_publ_author_name
'Zhang, Jian-Jian'
'Yan, Chang-Song'
'Peng, Yu'
'Luo, Zhen-Biao'
'Xu, Xiao-Bo'
'Wang, Ya-Wen'
_publ_section_title
;
 Total synthesis of (+-)-sacidumlignans D and A through Ueno-Stork radical
 cyclization reaction.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2498
_journal_page_last               2513
_journal_paper_doi               10.1039/c3ob00053b
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C18 H18 O2'
_chemical_formula_weight         266.32
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.570(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.517(6)
_cell_length_b                   10.598(7)
_cell_length_c                   16.662(11)
_cell_measurement_reflns_used    2074
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.33
_cell_measurement_theta_min      2.28
_cell_volume                     1499.2(18)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6977
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0452
_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)+(0.0576P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1286
_reflns_number_gt                1517
_reflns_number_total             2770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob00053b.txt
_cod_data_source_block           p21n
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1499.3(17)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7152842
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
C1 C 1.0964(2) 0.4041(2) 0.92319(13) 0.0616(6) Uani 1 1 d .
C2 C 1.0630(3) 0.2703(2) 0.94364(12) 0.0664(6) Uani 1 1 d .
H2 H 0.9638 0.2681 0.9696 0.080 Uiso 1 1 calc R
C3 C 1.0354(2) 0.20904(18) 0.86170(12) 0.0559(6) Uani 1 1 d .
H3 H 1.1387 0.1870 0.8438 0.067 Uiso 1 1 calc R
C4 C 0.9682(2) 0.31862(16) 0.80740(11) 0.0459(5) Uani 1 1 d .
C5 C 0.7904(2) 0.32864(17) 0.80400(11) 0.0482(5) Uani 1 1 d .
C6 C 0.7151(3) 0.3969(2) 0.86057(13) 0.0647(6) Uani 1 1 d .
H6 H 0.7740 0.4413 0.9006 0.078 Uiso 1 1 calc R
C7 C 0.5516(3) 0.3992(2) 0.85755(16) 0.0804(7) Uani 1 1 d .
H7 H 0.5020 0.4442 0.8962 0.096 Uiso 1 1 calc R
C8 C 0.4633(3) 0.3367(3) 0.79886(19) 0.0860(8) Uani 1 1 d .
H8 H 0.3539 0.3395 0.7970 0.103 Uiso 1 1 calc R
C9 C 0.5364(3) 0.2694(2) 0.74248(15) 0.0770(7) Uani 1 1 d .
H9 H 0.4765 0.2265 0.7021 0.092 Uiso 1 1 calc R
C10 C 0.6981(2) 0.2652(2) 0.74518(13) 0.0628(6) Uani 1 1 d .
H10 H 0.7463 0.2187 0.7067 0.075 Uiso 1 1 calc R
C11 C 1.0266(2) 0.32379(19) 0.72366(11) 0.0489(5) Uani 1 1 d .
C12 C 1.0901(2) 0.2225(2) 0.68691(13) 0.0674(6) Uani 1 1 d .
H12 H 1.0992 0.1455 0.7137 0.081 Uiso 1 1 calc R
C13 C 1.1414(3) 0.2332(3) 0.61000(15) 0.0853(8) Uani 1 1 d .
H13 H 1.1826 0.1633 0.5852 0.102 Uiso 1 1 calc R
C14 C 1.1312(3) 0.3456(4) 0.57123(16) 0.0939(9) Uani 1 1 d .
H14 H 1.1675 0.3531 0.5203 0.113 Uiso 1 1 calc R
C15 C 1.0681(3) 0.4475(3) 0.60647(16) 0.0927(8) Uani 1 1 d .
H15 H 1.0604 0.5244 0.5795 0.111 Uiso 1 1 calc R
C16 C 1.0156(3) 0.4363(2) 0.68221(13) 0.0701(7) Uani 1 1 d .
H16 H 0.9719 0.5061 0.7059 0.084 Uiso 1 1 calc R
C17 C 1.1904(3) 0.2127(3) 1.00108(16) 0.1148(10) Uani 1 1 d .
H17A H 1.1984 0.2593 1.0506 0.172 Uiso 1 1 calc R
H17B H 1.2894 0.2158 0.9773 0.172 Uiso 1 1 calc R
H17C H 1.1642 0.1265 1.0116 0.172 Uiso 1 1 calc R
C18 C 0.9380(3) 0.0887(2) 0.86049(14) 0.0783(7) Uani 1 1 d .
H18A H 0.8387 0.1057 0.8818 0.117 Uiso 1 1 calc R
H18B H 0.9935 0.0255 0.8928 0.117 Uiso 1 1 calc R
H18C H 0.9201 0.0589 0.8061 0.117 Uiso 1 1 calc R
O1 O 1.03635(15) 0.43086(12) 0.84808(8) 0.0563(4) Uani 1 1 d .
O2 O 1.16663(19) 0.48255(17) 0.96322(9) 0.0907(6) Uani 1 1 d .
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
O2 C1 O1 120.6(2)
O2 C1 C2 129.0(2)
O1 C1 C2 110.38(19)
C1 C2 C3 102.75(17)
C1 C2 C17 112.8(2)
C3 C2 C17 116.6(2)
C1 C2 H2 108.1
C3 C2 H2 108.1
C17 C2 H2 108.1
C2 C3 C18 114.67(18)
C2 C3 C4 103.20(16)
C18 C3 C4 116.36(17)
C2 C3 H3 107.4
C18 C3 H3 107.4
C4 C3 H3 107.4
O1 C4 C5 108.56(14)
O1 C4 C11 104.40(14)
C5 C4 C11 111.27(15)
O1 C4 C3 102.91(15)
C5 C4 C3 113.27(15)
C11 C4 C3 115.44(16)
C10 C5 C6 117.98(19)
C10 C5 C4 120.19(17)
C6 C5 C4 121.79(18)
C5 C6 C7 120.1(2)
C5 C6 H6 120.0
C7 C6 H6 120.0
C8 C7 C6 120.9(2)
C8 C7 H7 119.5
C6 C7 H7 119.5
C7 C8 C9 119.5(2)
C7 C8 H8 120.3
C9 C8 H8 120.3
C8 C9 C10 120.3(2)
C8 C9 H9 119.9
C10 C9 H9 119.9
C9 C10 C5 121.2(2)
C9 C10 H10 119.4
C5 C10 H10 119.4
C12 C11 C16 117.91(19)
C12 C11 C4 123.55(18)
C16 C11 C4 118.53(18)
C11 C12 C13 120.8(2)
C11 C12 H12 119.6
C13 C12 H12 119.6
C14 C13 C12 119.9(2)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.3(2)
C13 C14 H14 119.8
C15 C14 H14 119.8
C14 C15 C16 119.7(3)
C14 C15 H15 120.2
C16 C15 H15 120.2
C11 C16 C15 121.4(2)
C11 C16 H16 119.3
C15 C16 H16 119.3
C2 C17 H17A 109.5
C2 C17 H17B 109.5
H17A C17 H17B 109.5
C2 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C3 C18 H18A 109.5
C3 C18 H18B 109.5
H18A C18 H18B 109.5
C3 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C1 O1 C4 111.50(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.196(2)
C1 O1 1.344(2)
C1 C2 1.491(3)
C2 C3 1.513(3)
C2 C17 1.517(3)
C2 H2 0.9800
C3 C18 1.521(3)
C3 C4 1.553(3)
C3 H3 0.9800
C4 O1 1.466(2)
C4 C5 1.515(3)
C4 C11 1.519(3)
C5 C10 1.381(3)
C5 C6 1.385(3)
C6 C7 1.389(3)
C6 H6 0.9300
C7 C8 1.358(3)
C7 H7 0.9300
C8 C9 1.368(4)
C8 H8 0.9300
C9 C10 1.375(3)
C9 H9 0.9300
C10 H10 0.9300
C11 C12 1.368(3)
C11 C16 1.377(3)
C12 C13 1.391(3)
C12 H12 0.9300
C13 C14 1.354(4)
C13 H13 0.9300
C14 C15 1.361(4)
C14 H14 0.9300
C15 C16 1.377(3)
C15 H15 0.9300
C16 H16 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
O2 C1 C2 C3 -157.0(2)
O1 C1 C2 C3 22.1(2)
O2 C1 C2 C17 -30.5(3)
O1 C1 C2 C17 148.6(2)
C1 C2 C3 C18 -157.04(18)
C17 C2 C3 C18 79.1(3)
C1 C2 C3 C4 -29.48(19)
C17 C2 C3 C4 -153.4(2)
C2 C3 C4 O1 27.23(18)
C18 C3 C4 O1 153.71(17)
C2 C3 C4 C5 -89.78(18)
C18 C3 C4 C5 36.7(2)
C2 C3 C4 C11 140.28(17)
C18 C3 C4 C11 -93.2(2)
O1 C4 C5 C10 155.42(17)
C11 C4 C5 C10 41.1(2)
C3 C4 C5 C10 -90.9(2)
O1 C4 C5 C6 -26.9(2)
C11 C4 C5 C6 -141.28(19)
C3 C4 C5 C6 86.7(2)
C10 C5 C6 C7 0.6(3)
C4 C5 C6 C7 -177.08(19)
C5 C6 C7 C8 -1.0(3)
C6 C7 C8 C9 0.7(4)
C7 C8 C9 C10 0.0(4)
C8 C9 C10 C5 -0.4(3)
C6 C5 C10 C9 0.1(3)
C4 C5 C10 C9 177.82(19)
O1 C4 C11 C12 132.94(19)
C5 C4 C11 C12 -110.1(2)
C3 C4 C11 C12 20.7(3)
O1 C4 C11 C16 -47.0(2)
C5 C4 C11 C16 70.0(2)
C3 C4 C11 C16 -159.15(17)
C16 C11 C12 C13 -0.2(3)
C4 C11 C12 C13 179.9(2)
C11 C12 C13 C14 1.2(4)
C12 C13 C14 C15 -1.3(4)
C13 C14 C15 C16 0.5(4)
C12 C11 C16 C15 -0.6(3)
C4 C11 C16 C15 179.3(2)
C14 C15 C16 C11 0.5(4)
O2 C1 O1 C4 174.70(18)
C2 C1 O1 C4 -4.5(2)
C5 C4 O1 C1 105.64(16)
C11 C4 O1 C1 -135.58(16)
C3 C4 O1 C1 -14.66(18)
