Synthesis of 2,6-Hexa-tert-butylterphenyl Derivatives, 2,6-(2,4,6-t-Bu3C6H2)2C6H3X, where X = I, Li, OH, SH, N3, or NH2
Bukhryakov, Konstantin V.; Schrock, Richard R.; Hoveyda, Amir H.; Müller, Peter; Becker, Jonathan; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b01062

data_1545904
_publ_section_title
;
 Synthesis of 2,6-Hexa-tert-butylterphenyl Derivatives,
 2,6-(2,4,6-t-Bu3C6H2)2C6H3X, where X = I, Li, OH, SH, N3, or NH2
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b01062
_journal_year                    2017
_chemical_formula_sum            'C50 H81 Li O2'
_chemical_formula_weight         721.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.768(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7973(16)
_cell_length_b                   25.876(4)
_cell_length_c                   18.478(3)
_cell_measurement_reflns_used    9596
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.70
_cell_measurement_theta_min      2.35
_cell_volume                     4674.3(13)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            115474
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         1.356
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.059
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.025
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.860
_exptl_crystal_size_mid          0.670
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         13113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0702
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+4.1841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9825
_reflns_number_total             13113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01062_si_002.cif
_cod_data_source_block           X17076
_cod_original_cell_volume        4674.4(13)
_cod_database_code               1545904
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              35360
_shelx_hkl_checksum              1807