Synthesis of cyclobutane lignans via an organic single electron oxidant-electron relay system.
Riener, Michelle; Nicewicz, David A.; Chemical science (Royal Society of Chemistry : 2010) 4 (2013) 2625–; doi:10.1039/C3SC50643F

data_1514649
_publ_section_title
;
 Synthesis of cyclobutane lignans via an organic single electron
 oxidant-electron relay system.
;
_journal_issue                   6
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              2625
_journal_paper_doi               10.1039/C3SC50643F
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C22 H28 O6'
_chemical_formula_sum            'C22 H28 O6'
_chemical_formula_weight         388.44
_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     iterative
_audit_creation_date             2013-03-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled Mar 21 2013 11:17:50, GUI svn.r4446)
;
_cell_angle_alpha                115.546(5)
_cell_angle_beta                 90.919(6)
_cell_angle_gamma                98.363(6)
_cell_formula_units_Z            2
_cell_length_a                   5.0348(4)
_cell_length_b                   14.3242(9)
_cell_length_c                   15.1715(10)
_cell_measurement_reflns_used    1804
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.69
_cell_measurement_theta_min      3.47
_cell_volume                     972.89(13)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.1043
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8212
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.796
_diffrn_reflns_theta_min         3.241
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0772 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.8262.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0619P)^2^]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1578
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1831
_reflns_number_total             3264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3sc50643f.txt
_cod_data_source_block           x1303021
_cod_original_cell_volume        972.89(12)
_cod_database_code               1514649
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
C2(H2), C5(H5), C13(H13), C16(H16)
2.d Idealised Me refined as rotating group:
C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.744
_shelx_hkl_checksum              85439
_shelx_res_checksum              14773
_shelxl_version_number           2013-2