Stereochemistry of the Menthyl Grignard Reagent: Generation, Composition, Dynamics, and Reactions with Electrophiles.
Koller, Sebastian; Gatzka, Julia; Wong, Kit Ming; Altmann, Philipp J.; Pöthig, Alexander; Hintermann, Lukas; The Journal of organic chemistry 83 (2018) 15009–15028; doi:10.1021/acs.joc.8b02278

data_4037536
_publ_section_title
;
 Stereochemistry of the Menthyl Grignard Reagent: Generation, Composition,
 Dynamics, and Reactions with Electrophiles.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15009
_journal_page_last               15028
_journal_paper_doi               10.1021/acs.joc.8b02278
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C20 H38'
_chemical_formula_sum            'C20 H38'
_chemical_formula_weight         278.50
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      92
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2620(9)
_cell_length_b                   8.2620(9)
_cell_length_c                   27.103(3)
_cell_measurement_reflns_used    9110
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.3712
_cell_measurement_theta_min      2.5772
_cell_volume                     1850.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX III Control Software (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2014)'
_computing_structure_refinement
'SHELXL2014 (Sheldrick, 2014), SHELXLE (Huebschle, 2011)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 ' CMOS plate '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       ' \k-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker Photon CMOS '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  'Helios optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'IMS microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            137669
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         32.57
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.7281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5, Bruker, 2014'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.000
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.527
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.292
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.6(6)
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC^2^\L^3^/SIN(2\Q)]^-1/4^
_refine_ls_extinction_method     'shelxl-2014/7 (sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0425P)^2^+0.2217P] WHERE P=(FO^2^+2FC^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                3189
_reflns_number_total             3362
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo8b02278_si_003.cif
_cod_data_source_block           mo_hinlu9_0m-auto
_cod_original_cell_volume        1850.1(5)
_cod_database_code               4037536
_shelx_res_checksum              353
_shelx_hkl_checksum              62674