Chiral ruthenium Lewis acid catalyzed intramolecular Diels-Alder reactions.
Thamapipol, Sirinporn; Bernardinelli, Gérald; Besnard, Céline; Kündig, E Peter; Organic letters 12 (2010) 5604–5607; doi:10.1021/ol1019103

data_1503235
_publ_section_title
;
 Chiral ruthenium Lewis acid catalyzed intramolecular Diels-Alder
 reactions.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5604
_journal_page_last               5607
_journal_paper_doi               10.1021/ol1019103
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H14 Cl O3, C8 H12 N '
_chemical_formula_sum            'C18 H26 Cl N O3'
_chemical_formula_weight         339.86
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.616(5)
_cell_length_b                   11.220(3)
_cell_length_c                   27.785(9)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1750.8(17)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'IPDS (Stoe & Cie, 1996)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            15682
_diffrn_reflns_theta_full        28.318
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_min         5.009
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.29
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9952
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4322
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.0034668
_refine_ls_shift/su_mean         0.0003100
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 2.47 3.29 0.995 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0789
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0789
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              36
_reflns_limit_l_min              0
_reflns_number_gt                3825
_reflns_number_total             4322
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.92
_oxford_diffrn_Wilson_scale      16.84
_oxford_refine_ls_r_factor_ref   0.0351
_oxford_refine_ls_scale          0.21391(11)
_oxford_reflns_number_all        4322
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            ol1019103_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C18 H26 Cl1 N1 O3'
_cod_database_code               1503235