Collective synthesis of several 2,7'-cyclolignans and their correlation by chemical transformations.
Peng, Yu; Luo, Zhen-Biao; Zhang, Jian-Jian; Luo, Long; Wang, Ya-Wen; Organic & biomolecular chemistry 11 (2013) 7574–7586; doi:10.1039/c3ob41672k

data_7153170
_publ_section_title
;
 Collective synthesis of several 2,7'-cyclolignans and their correlation
 by chemical transformations.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7574
_journal_page_last               7586
_journal_paper_doi               10.1039/c3ob41672k
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         '2(C22 H26 O6), O'
_chemical_formula_sum            'C44 H52 O13'
_chemical_formula_weight         788.85
_chemical_name_systematic
;
 ?
;
_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             2013-06-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                85.685(8)
_cell_angle_beta                 80.440(8)
_cell_angle_gamma                89.993(7)
_cell_formula_units_Z            2
_cell_length_a                   8.1666(8)
_cell_length_b                   12.3232(10)
_cell_length_c                   20.795(2)
_cell_measurement_reflns_used    1201
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.7470
_cell_measurement_theta_min      4.0660
_cell_volume                     2057.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -82.00  -36.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 46

  2 omega  -78.00  -45.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 33

  3 omega  -21.00   29.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 50

  4 omega   40.00   70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 30

  5 omega  -42.00  -11.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000    0.0000 31

  6 omega   32.00  125.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -180.0000 93

  7 omega  -17.00   69.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -38.0000   60.0000 86

  8 omega   45.00   87.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  150.0000 42

  9 omega    5.00  101.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -120.0000 96

 10 omega    9.00   79.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -30.0000 70

 11 omega  -20.00  110.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -19.0000 -150.0000 130

 12 omega   73.00  109.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000  -60.0000 36

 13 omega   94.00  124.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000   60.0000 30

 14 omega  114.00  141.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000  -60.0000 27

 15 omega   69.00  110.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 41

 16 omega   52.00  105.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000    0.0000 53

 17 omega   49.00   74.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000   60.0000 25

 18 omega   47.00  106.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -60.0000 59

 19 omega   39.00  114.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 75

 20 omega  152.00  177.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000 -180.0000 25

 21 omega   80.00  106.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 26

 22 omega   95.00  144.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000   90.0000 49

 23 omega   89.00  168.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -120.0000 79

 24 omega   90.00  177.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000    0.0000 87

 25 omega  106.00  135.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  120.0000 29

 26 omega   55.00   97.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -180.0000 42

 27 omega   67.00  114.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 47

 28 omega  104.00  148.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000    0.0000 44

 29 omega   96.00  123.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000   30.0000 27

 30 omega   43.00   93.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   60.0000 50

 31 omega   55.00   92.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -30.0000 37

 32 omega   97.00  124.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000 -180.0000 27

 33 omega  143.00  171.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -60.0000 28

 34 omega  109.00  134.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -180.0000 25

 35 omega   88.00  178.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000  -60.0000 90

 36 omega   62.00   87.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -30.0000 25

 37 omega   39.00   74.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  150.0000 35

 38 omega  133.00  168.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 35

 39 omega   61.00   86.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0485081000
_diffrn_orient_matrix_UB_12      -0.1184553000
_diffrn_orient_matrix_UB_13      0.0247871000
_diffrn_orient_matrix_UB_21      0.1052451000
_diffrn_orient_matrix_UB_22      -0.0402635000
_diffrn_orient_matrix_UB_23      -0.0619707000
_diffrn_orient_matrix_UB_31      0.1522226000
_diffrn_orient_matrix_UB_32      -0.0079244000
_diffrn_orient_matrix_UB_33      0.0349625000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9890
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         4.054
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76996
_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_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.065
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         9890
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1727
_refine_ls_R_factor_gt           0.1125
_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^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2977
_refine_ls_wR_factor_ref         0.3393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5543
_reflns_number_total             9890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3ob41672k.txt
_cod_data_source_block           zhangjj0607_twin1_hklf4
_cod_database_code               7153170
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O14) \\sim Ueq, Uanis(O13) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: O14(0.5) O13(0.5)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C24(H24), C25(H25), C3(H3)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C42(H42), C38(H38), C9(H9), C30(H30), C27(H27), C20(H20), C16(H16),
 C19(H19), C39(H39)
4.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C), C34(H34A,H34B,H34C), C43(H43A,H43B,H43C), C13(H13A,H13B,H13C), C12(H12A,
 H12B,H12C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C44(H44A,H44B,H44C),
 C35(H35A,H35B,H35C)
4.d Idealised tetrahedral OH refined as rotating group:
 O7(H7), O2(H2)
;
_shelx_hkl_checksum              14225
_shelx_res_checksum              63615
_shelxl_version_number           2013-2