Enantioselective Oxidative Coupling of Carboxylic Acids to α-Branched Aldehydes.
Leth, Lars A.; Næsborg, Line; Reyes-Rodríguez, Gabriel J; Tobiesen, Henriette N.; Iversen, Marc V.; Jørgensen, Karl Anker; Journal of the American Chemical Society 140 (2018) 12687–12690; doi:10.1021/jacs.8b07394

data_4132910
_publ_section_title
;
 Enantioselective Oxidative Coupling of Carboxylic Acids to \a-Branched
 Aldehydes.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12687
_journal_page_last               12690
_journal_paper_doi               10.1021/jacs.8b07394
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 Cl O4'
_chemical_formula_sum            'C21 H17 Cl O4'
_chemical_formula_weight         368.82
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4513(6)
_cell_length_b                   12.5611(11)
_cell_length_c                   18.4953(15)
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100
_cell_measurement_theta_max      24
_cell_measurement_theta_min      2.56
_cell_volume                     1731.1(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9977
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       '\f-scans and \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Ag K\a'
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27153
_diffrn_reflns_theta_full        23.6730
_diffrn_reflns_theta_max         23.67
_diffrn_reflns_theta_min         1.55
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.7215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0951 before and 0.0382 after correction.
The Ratio of minimum to maximum transmission is 0.9686.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4150
_exptl_crystal_description       block
_exptl_crystal_F_000             768.5561
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.4267
_refine_diff_density_min         -0.1972
_refine_diff_density_rms         0.0501
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_d_res_high            0.6984
_refine_ls_d_res_low             10.3912
_refine_ls_goodness_of_fit_ref   0.8658
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8658
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              26
_reflns_limit_l_min              -26
_reflns_number_gt                5124
_reflns_number_total             5303
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja8b07394_si_002.cif
_cod_data_source_block           2018_01_22_2_0m
_cod_original_cell_volume        1731.1(3)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4132910
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00O(H00O), C00N(H00N), C008(H008), C00J(H00J), C00K(H00K),
 C009(H009), C00F(H00F), C00B(H00B), C00H(H00H), C006(H006)
2.b Idealised Me refined as rotating group:
 C00P(H00a,H00c,H00d), C00Q(H00e,H00g,H00i)
;