Formation of enantioenriched alkanol with stochastic distribution of enantiomers in the absolute asymmetric synthesis under heterogeneous solid-vapor phase conditions
Kaimori, Yoshiyasu; Hiyoshi, Yui; Kawasaki, Tsuneomi; Matsumoto, Arimasa; Soai, Kenso; Chemical Communications  (2019) –; doi:10.1039/C9CC01875A

data_7123265
_publ_section_title
;
 Formation of enantioenriched alkanol with stochastic distribution of
 enantiomers in the absolute asymmetric synthesis under heterogeneous
 solid-vapor phase conditions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01875A
_journal_year                    2019
_chemical_formula_moiety         'C11 H12 N2 O'
_chemical_formula_sum            'C11 H12 N2 O'
_chemical_formula_weight         188.23
_chemical_name_common
2-(3,3-dimethylbut-1-yn-1-yl)pyrimidine-5-carbaldehyde
_chemical_name_systematic        2-tert-ButylethynylpyrimidineCarbaldehyde
_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
_audit_update_record
;
2016-12-26 deposited with the CCDC.    2019-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.5574(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6977(6)
_cell_length_b                   5.6969(6)
_cell_length_c                   32.062(3)
_cell_measurement_reflns_used    399
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.8761
_cell_measurement_theta_min      3.9678
_cell_volume                     1040.32(18)
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
'Shelxle (J. Appl. Cryst., 44, (2011) 1281-1284.)'
_computing_publication_material
'Shelxle (J. Appl. Cryst., 44, (2011) 1281-1284.)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            11376
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.778
_diffrn_reflns_theta_min         2.542
_diffrn_source                   'fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear white'
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.764
_exptl_crystal_size_mid          0.530
_exptl_crystal_size_min          0.236
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.178(11)
_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   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0626P)^2^+0.3982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2459
_reflns_number_total             2554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01875a2.cif
_cod_data_source_block           harf_P21n
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_secondary' value 'diffmap' was changed to
'difmap'.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1040.33(19)
_cod_database_code               7123265
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              4010