Practical, Scalable, High-Throughput Approaches to η^3^-Pyranil and η^3^-Pyridinyl Organometallic Enantiomeric Scaffolds Using the Achmatowicz Reaction
Thomas C. Coombs; Lee, IV, Maurice D.; Heilam Wong; Matthew Armstrong; Bo Cheng; Wenyong Chen; Alessandro F. Moretto; Lanny S. Liebeskind; Journal of Organic Chemistry 73 (2008) 882–888; doi:10.1021/jo702006z

data_4023229
_publ_section_title
;
 Practical, Scalable, High-Throughput Approaches to \h^3^-Pyranil
 and \h^3^-Pyridinyl Organometallic Enantiomeric Scaffolds
 Using the Achmatowicz Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              882
_journal_page_last               888
_journal_paper_doi               10.1021/jo702006z
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         '[C17 H17 B Mo N6 O4],0.25[C H2 Cl2]'
_chemical_formula_sum            'C17.25 H17.5 B Cl0.5 Mo N6 O4'
_chemical_formula_weight         497.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.992(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.9826(4)
_cell_length_b                   10.7528(4)
_cell_length_c                   34.9644(12)
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33.92
_cell_measurement_theta_min      2.22
_cell_volume                     4123.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            73316
_diffrn_reflns_theta_full        34.92
_diffrn_reflns_theta_max         34.92
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.8974
_exptl_absorpt_correction_T_min  0.7823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10, Sheldrick 2003'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irreg
_exptl_crystal_F_000             2004
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.683
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.177
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1103
_refine_ls_number_reflns         32017
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+3.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1547
_reflns_number_gt                27772
_reflns_number_total             32017
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702006z-File006.cif
_cod_data_source_block           mlesyn
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C17.25 H17.50 B Cl0.50 Mo N6 O4'
_cod_database_code               4023229