First diastereoselective synthesis of methyl caffeoyl- and feruloyl-muco-quinates.
Jaiswal, Rakesh; Dickman, Michael H.; Kuhnert, Nikolai; Organic & biomolecular chemistry 10 (2012) 5266–5277; doi:10.1039/c2ob25124h

data_7152403
_publ_section_title
;
 First diastereoselective synthesis of methyl caffeoyl- and
 feruloyl-muco-quinates.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5266
_journal_page_last               5277
_journal_paper_doi               10.1039/c2ob25124h
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C11 H9 Cl3 O4'
_chemical_formula_weight         311.53
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.717(2)
_cell_angle_beta                 83.067(2)
_cell_angle_gamma                84.035(2)
_cell_formula_units_Z            4
_cell_length_a                   5.6867(2)
_cell_length_b                   10.1514(4)
_cell_length_c                   22.3376(9)
_cell_measurement_reflns_used    3520
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.24
_cell_measurement_theta_min      3.32
_cell_volume                     1270.62(8)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17407
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  0.8589
_exptl_absorpt_correction_T_min  0.7526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0183(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0436
_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/[\s^2^(Fo^2^)+(0.0370P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                3945
_reflns_number_total             5802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25124h.txt
_cod_data_source_block           mtc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7152403