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_4033774
_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         'C19 H22 O2 Sn'
_chemical_formula_sum            'C19 H22 O2 Sn'
_chemical_formula_weight         401.05
_chemical_name_common            JS2RL158
_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             2017-02-16T16:53:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                75.0600(10)
_cell_angle_beta                 83.8440(10)
_cell_angle_gamma                85.4200(10)
_cell_formula_units_Z            2
_cell_length_a                   7.69440(10)
_cell_length_b                   8.8116(2)
_cell_length_c                   12.8831(3)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.9
_cell_measurement_theta_min      2.4
_cell_measurement_wavelength     0.71073
_cell_volume                     837.84(3)
_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 0.988
_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      0.021329
_diffrn_orient_matrix_UB_12      0.036743
_diffrn_orient_matrix_UB_13      -0.080244
_diffrn_orient_matrix_UB_21      0.006938
_diffrn_orient_matrix_UB_22      0.110205
_diffrn_orient_matrix_UB_23      0.006036
_diffrn_orient_matrix_UB_31      0.128976
_diffrn_orient_matrix_UB_32      -0.018492
_diffrn_orient_matrix_UB_33      0.005579
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            35332
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.988
_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         31.82
_diffrn_reflns_theta_min         2.396
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.529
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.616
_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    1.59
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     205
_refine_ls_number_reflns         5667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+0.1460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0549
_reflns_Friedel_coverage         0
_reflns_number_gt                5130
_reflns_number_total             5667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02891_si_006.cif
_cod_data_source_block           shelx
_cod_database_code               4033774
_shelx_estimated_absorpt_t_min   0.553
_shelx_estimated_absorpt_t_max   0.76
_shelx_res_checksum              71242
_shelx_hkl_checksum              2246