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_4037535
_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         'C15 H27 N O3'
_chemical_formula_sum            'C15 H27 N O3'
_chemical_formula_weight         269.38
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 99.897(4)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   14.4289(12)
_cell_length_b                   9.7749(9)
_cell_length_c                   35.171(3)
_cell_measurement_reflns_used    9710
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.7700
_cell_measurement_theta_min      2.5288
_cell_volume                     4886.7(7)
_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                 ' CCD '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       ' \k-geometry diffractometer '
_diffrn_measurement_device_type  ' Apex II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  'Triumph monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            81224
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5, Bruker, 2014'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.559
_exptl_crystal_size_mid          0.463
_exptl_crystal_size_min          0.382
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.06(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1069
_refine_ls_number_reflns         17262
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'W=1/[\S^2^(FO^2^)+(0.0400P)^2^+1.3277P] WHERE P=(FO^2^+2FC^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                16257
_reflns_number_total             17262
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo8b02278_si_004.cif
_cod_data_source_block           gatju2-auto
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037535
_shelx_res_checksum              19039
_shelx_hkl_checksum              49153