Titanium(iv) enolates of cyclic ketones – stereoselective addition of cyclododecanone to aromatic aldehydes
Cież, Dariusz; Pałasz, Aleksandra; Kozieł, Krzysztof; Lutsan, Antonii; Kalinowska-Tłuścik, Justyna; New Journal of Chemistry 47 (2023) 16505–16517; doi:10.1039/D3NJ02355A

data_7062669
_publ_section_title
;
 Titanium(iv) enolates of cyclic ketones -- stereoselective addition of
 cyclododecanone to aromatic aldehydes
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16505
_journal_page_last               16517
_journal_paper_doi               10.1039/D3NJ02355A
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H30 O3'
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_weight         318.44
_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
_audit_creation_date             2020-06-17T21:22:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-03-03 deposited with the CCDC.	2023-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.556(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
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_cell_length_b                   5.37030(10)
_cell_length_c                   14.0036(2)
_cell_measurement_reflns_used    7694
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.867
_cell_measurement_theta_min      3.248
_cell_volume                     867.02(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0983314
_diffrn_orient_matrix_UB_12      0.0017366
_diffrn_orient_matrix_UB_13      0.0594215
_diffrn_orient_matrix_UB_21      0.0904865
_diffrn_orient_matrix_UB_22      -0.0025338
_diffrn_orient_matrix_UB_23      0.0948411
_diffrn_orient_matrix_UB_31      0.0013972
_diffrn_orient_matrix_UB_32      0.2867893
_diffrn_orient_matrix_UB_33      0.0004894
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16671
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.195
_diffrn_reflns_theta_min         3.21
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.63
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.52186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.22
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(10)
_refine_ls_extinction_coef       0.0116(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.031
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0431P)^2^+0.1747P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0796
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                3110
_reflns_number_total             3187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02355a2.cif
_cod_data_source_block           1s96_syn
_cod_depositor_comments          'Adding full bibliography for 7062669.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7062669
_shelx_estimated_absorpt_t_min   0.834
_shelx_estimated_absorpt_t_max   0.969
_shelx_shelxl_version_number     2018/1