#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:57:39 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230672 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/60/7156029.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_7156029
loop_
_publ_author_name
'Jagtap, Pratap R.'
'Císařová, Ivana'
'Jahn, Ullrich'
_publ_section_title
;
 Bioinspired total synthesis of tetrahydrofuran lignans by tandem
 nucleophilic addition/redox isomerization/oxidative coupling and
 cycloetherification reactions as key steps.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              750
_journal_page_last               755
_journal_paper_doi               10.1039/c7ob02848b
_journal_volume                  16
_journal_year                    2018
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C30 H26 O2'
_chemical_formula_sum            'C30 H26 O2'
_chemical_formula_weight         418.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-16 deposited with the CCDC.
2017-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                89.4600(10)
_cell_angle_beta                 73.2660(10)
_cell_angle_gamma                88.8100(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2432(2)
_cell_length_b                   10.4558(3)
_cell_length_c                   13.9905(4)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.3971
_cell_measurement_theta_min      3.2986
_cell_volume                     1154.51(5)
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service v4.2.9'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/4'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18313
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.390
_diffrn_reflns_theta_min         3.299
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            coloutless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0077(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0511P)²+0.2603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3867
_reflns_number_total             4541
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ob02848b2.cif
_cod_data_source_block           cu_jpu_456_2_jahn
_cod_depositor_comments
'Adding full bibliography for 7156027--7156031.cif.'
_cod_database_code               7156029
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.870
_shelx_estimated_absorpt_t_max   0.934
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1A C 0.54655(13) 0.74936(10) 0.38394(8) 0.0214(2) Uani 1 1 d . .
C2A C 0.59618(14) 0.78716(11) 0.28405(8) 0.0248(3) Uani 1 1 d . .
H2A H 0.6493 0.8671 0.2655 0.030 Uiso 1 1 calc R U
C3A C 0.56783(15) 0.70759(13) 0.21154(9) 0.0307(3) Uani 1 1 d . .
H3A H 0.6049 0.7318 0.1432 0.037 Uiso 1 1 calc R U
C4A C 0.48545(16) 0.59305(13) 0.23918(10) 0.0337(3) Uani 1 1 d . .
H4A H 0.4635 0.5400 0.1897 0.040 Uiso 1 1 calc R U
C5A C 0.43490(16) 0.55530(12) 0.33832(10) 0.0344(3) Uani 1 1 d . .
H5A H 0.3780 0.4768 0.3568 0.041 Uiso 1 1 calc R U
C6A C 0.46755(15) 0.63225(11) 0.41042(9) 0.0272(3) Uani 1 1 d . .
H6A H 0.4360 0.6052 0.4782 0.033 Uiso 1 1 calc R U
C7A C 0.57881(13) 0.82842(11) 0.46468(8) 0.0217(2) Uani 1 1 d . .
C8A C 0.57560(13) 0.97438(10) 0.45704(8) 0.0212(2) Uani 1 1 d . .
H8A H 0.5586 1.0001 0.3915 0.025 Uiso 1 1 calc R U
C9A C 0.74552(14) 1.02655(12) 0.46393(9) 0.0264(3) Uani 1 1 d . .
H9A1 H 0.7403 1.1212 0.4629 0.032 Uiso 1 1 calc R U
H9A2 H 0.7633 0.9993 0.5282 0.032 Uiso 1 1 calc R U
C10A C 0.89371(13) 0.98024(11) 0.37935(8) 0.0228(2) Uani 1 1 d . .
C11A C 0.99111(15) 0.87434(12) 0.39107(9) 0.0286(3) Uani 1 1 d . .
H11A H 0.9657 0.8316 0.4537 0.034 Uiso 1 1 calc R U
C12A C 1.12489(15) 0.83026(12) 0.31254(10) 0.0319(3) Uani 1 1 d . .
H12A H 1.1901 0.7576 0.3216 0.038 Uiso 1 1 calc R U
C13A C 1.16319(15) 0.89194(13) 0.22126(9) 0.0313(3) Uani 1 1 d . .
H13A H 1.2546 0.8618 0.1674 0.038 Uiso 1 1 calc R U
C14A C 1.06779(16) 0.99801(13) 0.20844(9) 0.0326(3) Uani 1 1 d . .
H14A H 1.0942 1.0410 0.1459 0.039 Uiso 1 1 calc R U
C15A C 0.93372(15) 1.04128(12) 0.28705(9) 0.0283(3) Uani 1 1 d . .
H15A H 0.8683 1.1137 0.2777 0.034 Uiso 1 1 calc R U
O1A O 0.60334(11) 0.77708(8) 0.53801(6) 0.0312(2) Uani 1 1 d . .
C1B C 0.16555(15) 0.74882(11) 0.90864(8) 0.0252(3) Uani 1 1 d . .
C2B C 0.17865(18) 0.86630(13) 0.95158(10) 0.0352(3) Uani 1 1 d . .
H2B H 0.0906 0.8957 1.0076 0.042 Uiso 1 1 calc R U
C3B C 0.3201(2) 0.94043(14) 0.91273(12) 0.0467(4) Uani 1 1 d . .
H3B H 0.3301 1.0199 0.9427 0.056 Uiso 1 1 calc R U
C4B C 0.44706(19) 0.89826(15) 0.82983(12) 0.0456(4) Uani 1 1 d . .
H4B H 0.5443 0.9488 0.8034 0.055 Uiso 1 1 calc R U
C5B C 0.43276(16) 0.78321(13) 0.78561(10) 0.0363(3) Uani 1 1 d . .
H5B H 0.5186 0.7561 0.7278 0.044 Uiso 1 1 calc R U
C6B C 0.29355(15) 0.70718(12) 0.82534(9) 0.0284(3) Uani 1 1 d . .
H6B H 0.2854 0.6270 0.7959 0.034 Uiso 1 1 calc R U
C7B C 0.01000(15) 0.67299(12) 0.95243(8) 0.0254(3) Uani 1 1 d . .
C8B C 0.01825(14) 0.52712(11) 0.94629(8) 0.0246(3) Uani 1 1 d . .
H8B H 0.1346 0.4992 0.9064 0.029 Uiso 1 1 calc R U
C9B C -0.11129(16) 0.48155(13) 0.89383(9) 0.0312(3) Uani 1 1 d . .
H9B1 H -0.1149 0.3870 0.8959 0.037 Uiso 1 1 calc R U
H9B2 H -0.2255 0.5152 0.9298 0.037 Uiso 1 1 calc R U
C10B C -0.06493(15) 0.52646(12) 0.78632(9) 0.0265(3) Uani 1 1 d . .
C11B C -0.13683(15) 0.63724(12) 0.75844(9) 0.0294(3) Uani 1 1 d . .
H11B H -0.2194 0.6849 0.8073 0.035 Uiso 1 1 calc R U
C12B C -0.08879(16) 0.67856(12) 0.65984(9) 0.0308(3) Uani 1 1 d . .
H12B H -0.1394 0.7537 0.6414 0.037 Uiso 1 1 calc R U
C13B C 0.03257(16) 0.61053(13) 0.58854(9) 0.0311(3) Uani 1 1 d . .
H13B H 0.0658 0.6391 0.5212 0.037 Uiso 1 1 calc R U
C14B C 0.10557(16) 0.50073(13) 0.61542(9) 0.0320(3) Uani 1 1 d . .
H14B H 0.1892 0.4540 0.5665 0.038 Uiso 1 1 calc R U
C15B C 0.05674(16) 0.45890(12) 0.71357(9) 0.0302(3) Uani 1 1 d . .
H15B H 0.1069 0.3832 0.7315 0.036 Uiso 1 1 calc R U
O1B O -0.12353(11) 0.72683(9) 0.99535(7) 0.0377(2) 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 0.0181 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2A C1A C6A 119.60(11) . .
C2A C1A C7A 122.37(10) . .
C6A C1A C7A 118.02(10) . .
C3A C2A C1A 119.86(11) . .
C3A C2A H2A 120.1 . .
C1A C2A H2A 120.1 . .
C4A C3A C2A 119.91(12) . .
C4A C3A H3A 120.0 . .
C2A C3A H3A 120.0 . .
C5A C4A C3A 120.49(12) . .
C5A C4A H4A 119.8 . .
C3A C4A H4A 119.8 . .
C4A C5A C6A 119.82(12) . .
C4A C5A H5A 120.1 . .
C6A C5A H5A 120.1 . .
C5A C6A C1A 120.27(11) . .
C5A C6A H6A 119.9 . .
C1A C6A H6A 119.9 . .
O1A C7A C1A 120.21(10) . .
O1A C7A C8A 119.80(10) . .
C1A C7A C8A 119.97(9) . .
C7A C8A C9A 109.47(9) . .
C7A C8A C8A 107.88(11) . 2_676
C9A C8A C8A 111.56(11) . 2_676
C7A C8A H8A 109.3 . .
C9A C8A H8A 109.3 . .
C8A C8A H8A 109.3 2_676 .
C10A C9A C8A 112.27(9) . .
C10A C9A H9A1 109.2 . .
C8A C9A H9A1 109.2 . .
C10A C9A H9A2 109.2 . .
C8A C9A H9A2 109.2 . .
H9A1 C9A H9A2 107.9 . .
C15A C10A C11A 118.40(10) . .
C15A C10A C9A 120.55(10) . .
C11A C10A C9A 121.03(11) . .
C12A C11A C10A 120.91(11) . .
C12A C11A H11A 119.5 . .
C10A C11A H11A 119.5 . .
C13A C12A C11A 120.03(11) . .
C13A C12A H12A 120.0 . .
C11A C12A H12A 120.0 . .
C12A C13A C14A 119.79(11) . .
C12A C13A H13A 120.1 . .
C14A C13A H13A 120.1 . .
C13A C14A C15A 119.93(12) . .
C13A C14A H14A 120.0 . .
C15A C14A H14A 120.0 . .
C14A C15A C10A 120.93(11) . .
C14A C15A H15A 119.5 . .
C10A C15A H15A 119.5 . .
C2B C1B C6B 119.81(12) . .
C2B C1B C7B 118.10(11) . .
C6B C1B C7B 122.07(11) . .
C3B C2B C1B 120.04(13) . .
C3B C2B H2B 120.0 . .
C1B C2B H2B 120.0 . .
C2B C3B C4B 119.81(14) . .
C2B C3B H3B 120.1 . .
C4B C3B H3B 120.1 . .
C5B C4B C3B 120.34(13) . .
C5B C4B H4B 119.8 . .
C3B C4B H4B 119.8 . .
C4B C5B C6B 120.20(13) . .
C4B C5B H5B 119.9 . .
C6B C5B H5B 119.9 . .
C5B C6B C1B 119.77(12) . .
C5B C6B H6B 120.1 . .
C1B C6B H6B 120.1 . .
O1B C7B C1B 120.30(11) . .
O1B C7B C8B 119.56(11) . .
C1B C7B C8B 120.12(10) . .
C7B C8B C9B 109.14(10) . .
C7B C8B C8B 108.21(11) . 2_567
C9B C8B C8B 112.02(12) . 2_567
C7B C8B H8B 109.1 . .
C9B C8B H8B 109.1 . .
C8B C8B H8B 109.1 2_567 .
C10B C9B C8B 111.13(10) . .
C10B C9B H9B1 109.4 . .
C8B C9B H9B1 109.4 . .
C10B C9B H9B2 109.4 . .
C8B C9B H9B2 109.4 . .
H9B1 C9B H9B2 108.0 . .
C15B C10B C11B 118.67(11) . .
C15B C10B C9B 119.76(11) . .
C11B C10B C9B 121.53(11) . .
C12B C11B C10B 120.52(11) . .
C12B C11B H11B 119.7 . .
C10B C11B H11B 119.7 . .
C13B C12B C11B 120.08(11) . .
C13B C12B H12B 120.0 . .
C11B C12B H12B 120.0 . .
C12B C13B C14B 119.93(11) . .
C12B C13B H13B 120.0 . .
C14B C13B H13B 120.0 . .
C13B C14B C15B 120.01(12) . .
C13B C14B H14B 120.0 . .
C15B C14B H14B 120.0 . .
C14B C15B C10B 120.78(11) . .
C14B C15B H15B 119.6 . .
C10B C15B H15B 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C2A 1.3942(16) .
C1A C6A 1.3951(16) .
C1A C7A 1.4932(15) .
C2A C3A 1.3916(17) .
C2A H2A 0.9500 .
C3A C4A 1.3852(19) .
C3A H3A 0.9500 .
C4A C5A 1.385(2) .
C4A H4A 0.9500 .
C5A C6A 1.3849(18) .
C5A H5A 0.9500 .
C6A H6A 0.9500 .
C7A O1A 1.2191(14) .
C7A C8A 1.5291(15) .
C8A C9A 1.5424(15) .
C8A C8A 1.551(2) 2_676
C8A H8A 1.0000 .
C9A C10A 1.5102(15) .
C9A H9A1 0.9900 .
C9A H9A2 0.9900 .
C10A C15A 1.3898(16) .
C10A C11A 1.3903(16) .
C11A C12A 1.3880(17) .
C11A H11A 0.9500 .
C12A C13A 1.3810(18) .
C12A H12A 0.9500 .
C13A C14A 1.3863(18) .
C13A H13A 0.9500 .
C14A C15A 1.3871(17) .
C14A H14A 0.9500 .
C15A H15A 0.9500 .
C1B C2B 1.3922(18) .
C1B C6B 1.3941(16) .
C1B C7B 1.4929(17) .
C2B C3B 1.385(2) .
C2B H2B 0.9500 .
C3B C4B 1.388(2) .
C3B H3B 0.9500 .
C4B C5B 1.380(2) .
C4B H4B 0.9500 .
C5B C6B 1.3856(18) .
C5B H5B 0.9500 .
C6B H6B 0.9500 .
C7B O1B 1.2203(14) .
C7B C8B 1.5275(16) .
C8B C9B 1.5443(17) .
C8B C8B 1.550(2) 2_567
C8B H8B 1.0000 .
C9B C10B 1.5140(16) .
C9B H9B1 0.9900 .
C9B H9B2 0.9900 .
C10B C15B 1.3918(17) .
C10B C11B 1.3932(17) .
C11B C12B 1.3884(17) .
C11B H11B 0.9500 .
C12B C13B 1.3824(18) .
C12B H12B 0.9500 .
C13B C14B 1.3838(18) .
C13B H13B 0.9500 .
C14B C15B 1.3844(17) .
C14B H14B 0.9500 .
C15B H15B 0.9500 .
