Synthesis of chiral cyclobutanes via rhodium/diene-catalyzed asymmetric 1,4-addition: a dramatic ligand effect on the diastereoselectivity
Ya-Jing Chen; Tian-Jiao Hu; Chen-Guo Feng; Guo-Qiang Lin; Chem.Commun. 51 (2015) 8773–; doi:10.1039/C5cc02023A

data_7117157
_publ_section_title
;
 Synthesis of chiral cyclobutanes via rhodium/diene-catalyzed asymmetric
 1,4-addition: a dramatic ligand effect on the diastereoselectivity
;
_journal_name_full               Chem.Commun.
_journal_page_first              8773
_journal_paper_doi               10.1039/C5cc02023A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C29 H23 Br O2'
_chemical_formula_weight         483.38
_chemical_melting_point          376.5(15)
_chemical_name_systematic
'(1S, 2S)-[1,1':3',1''-Terphenyl]-2'-yl 2-(4-bromophenyl)cyclobutanecarboxylate'
_chemical_properties_physical    'stable in air at room temperature'
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-01-12 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                89.509(5)
_cell_angle_beta                 70.585(5)
_cell_angle_gamma                71.497(5)
_cell_formula_units_Z            2
_cell_length_a                   9.845(2)
_cell_length_b                   10.370(2)
_cell_length_c                   12.763(3)
_cell_measurement_reflns_used    2241
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.895
_cell_measurement_theta_min      5.087
_cell_volume                     1158.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7085
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.083
_exptl_absorpt_coefficient_mu    1.798
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             496
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane/dichloromethane'
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0724P)^2^+0.2466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1329
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3321
_reflns_number_total             4555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc02023a2.cif
_cod_data_source_block           cd214672
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '375-378' was changed to '376.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        1158.5(5)
_cod_database_code               7117157
_shelxl_version_number           2013-4
_shelx_res_checksum              31133
_shelx_hkl_checksum              31145