C-C Bond-Forming and Bond-Breaking Processes from the Reaction of Diesters with Me<sub>3</sub>SnLi. Synthesis of Complex Bridged Polycycles and Dialkyl Aromatic Compounds.
Martínez-García, Lucas; Lobato, Rubén; Prado, Gustavo; Monje, Pablo; Sardina, F. Javier; Paleo, M. Rita; The Journal of organic chemistry 84 (2019) 1887–1897; doi:10.1021/acs.joc.8b02891

data_4033764
_publ_section_title
;
 C-C Bond-Forming and Bond-Breaking Processes from the Reaction of
 Diesters with Me<sub>3</sub>SnLi. Synthesis of Complex Bridged Polycycles
 and Dialkyl Aromatic Compounds.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1887
_journal_page_last               1897
_journal_paper_doi               10.1021/acs.joc.8b02891
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C22 H28 O Sn'
_chemical_formula_sum            'C22 H28 O Sn'
_chemical_formula_weight         427.13
_chemical_name_common            jslm421c
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2017-02-27T10:21:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                109.3120(10)
_cell_angle_beta                 98.6220(10)
_cell_angle_gamma                100.7140(10)
_cell_formula_units_Z            4
_cell_length_a                   8.9654(2)
_cell_length_b                   13.7149(3)
_cell_length_c                   17.4475(4)
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.48
_cell_measurement_theta_min      2.37
_cell_measurement_wavelength     0.71073
_cell_volume                     1936.94(8)
_computing_cell_refinement       'SAINT V8.37A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      0.112129
_diffrn_orient_matrix_UB_12      0.03237
_diffrn_orient_matrix_UB_13      0.02945
_diffrn_orient_matrix_UB_21      0.016378
_diffrn_orient_matrix_UB_22      -0.072922
_diffrn_orient_matrix_UB_23      -0.009813
_diffrn_orient_matrix_UB_31      0.027422
_diffrn_orient_matrix_UB_32      -0.003132
_diffrn_orient_matrix_UB_33      -0.054102
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            74719
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.598
_diffrn_reflns_theta_min         1.626
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.324
_exptl_absorpt_correction_T_max  0.802
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.57
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     449
_refine_ls_number_reflns         12879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0224P)^2^+1.1612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0518
_refine_ls_wR_factor_ref         0.0551
_reflns_Friedel_coverage         0
_reflns_number_gt                10642
_reflns_number_total             12879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02891_si_012.cif
_cod_data_source_block           shelx
_cod_database_code               4033764
_shelx_estimated_absorpt_t_min   0.587
_shelx_estimated_absorpt_t_max   0.89
_shelx_res_checksum              85814
_shelx_hkl_checksum              21945