Synthesis of Sterically Hindered β-Diketones via Condensation of Acid Chlorides with Enolates.
Crossman, Aaron S.; Larson, Alec T.; Shi, Jake X.; Krajewski, Sebastian M.; Akturk, Eser S.; Marshak, Michael P.; The Journal of organic chemistry 84 (2019) 7434–7442; doi:10.1021/acs.joc.9b00433

data_4034582
_publ_section_title
;
 Synthesis of Sterically Hindered \b-Diketones via Condensation of Acid
 Chlorides with Enolates.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7434
_journal_page_last               7442
_journal_paper_doi               10.1021/acs.joc.9b00433
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C43 H60 O2'
_chemical_formula_sum            'C43 H60 O2'
_chemical_formula_weight         608.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.745(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9091(9)
_cell_length_b                   18.6490(12)
_cell_length_c                   16.3846(11)
_cell_measurement_reflns_used    9792
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.46
_cell_measurement_theta_min      2.61
_cell_volume                     3777.2(4)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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  0.0408
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            180462
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.621
_diffrn_reflns_theta_min         2.541
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0435 before and 0.0398 after correction. The Ratio of minimum to maximum transmission is 0.9526. The \l/2 correction factor is Not present.'
_exptl_crystal_density_diffrn    1.071
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.411
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         12617
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0709P)^2^+1.5231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10158
_reflns_number_total             12617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00433_si_002.cif
_cod_data_source_block           tripach
_cod_database_code               4034582
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.969
_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. Restrained distances
 H2-O2
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C16(H16), C19(H19), C22(H22), C31(H31), C34(H34), C37(H37)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14), C27(H27), C29(H29)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C32(H32A,H32B,H32C), C33(H33A,
 H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C38(H38A,H38B,H38C),
 C39(H39A,H39B,H39C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,
 H43C)
;
_shelx_res_checksum              71599
_olex2_submission_special_instructions 'No special instructions were received'