Explorations of caffeic acid derivatives: total syntheses of rufescenolide, yunnaneic acids C and D, and studies toward yunnaneic acids A and B.
Griffith, Daniel R.; Botta, Lorenzo; St Denis, Tyler G.; Snyder, Scott A.; The Journal of organic chemistry 79 (2014) 88–105; doi:10.1021/jo4023167

data_4029085
_publ_section_title
;
 Explorations of caffeic acid derivatives: total syntheses of
 rufescenolide, yunnaneic acids C and D, and studies toward yunnaneic
 acids A and B.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              88
_journal_page_last               105
_journal_paper_doi               10.1021/jo4023167
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C46 H46 Br2 Cl6 O16'
_chemical_formula_weight         1227.35
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 92.484(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.173(8)
_cell_length_b                   16.235(4)
_cell_length_c                   21.928(6)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.28
_cell_volume                     10376(5)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0975
_diffrn_reflns_av_sigmaI/netI    0.0854
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            83140
_diffrn_reflns_theta_full        30.76
_diffrn_reflns_theta_max         30.76
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    1.939
_exptl_absorpt_correction_T_max  0.9093
_exptl_absorpt_correction_T_min  0.6033
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4976
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.541
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         16113
_refine_ls_number_restraints     126
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1477
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1197P)^2^+12.2972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2007
_refine_ls_wR_factor_ref         0.2383
_reflns_number_gt                8627
_reflns_number_total             16113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4023167_si_005.cif
_cod_data_source_block           dg15s10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4029085