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_4034583
_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         'C47 H52 O2'
_chemical_formula_sum            'C47 H52 O2'
_chemical_formula_weight         648.88
_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                 94.938(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5479(12)
_cell_length_b                   13.8161(12)
_cell_length_c                   19.0946(16)
_cell_measurement_reflns_used    9675
_cell_measurement_temperature    109(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.60
_cell_volume                     3823.7(6)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      108.97
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.969
_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  0.0585
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            79404
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.809
_diffrn_reflns_theta_min         2.356
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0849 before and 0.0706 after correction. The Ratio of minimum to maximum transmission is 0.8755. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.654
_exptl_crystal_size_mid          0.459
_exptl_crystal_size_min          0.421
_refine_diff_density_max         1.099
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         14903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.2031
_refine_ls_R_factor_gt           0.1876
_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^)+(0.0887P)^2^+75.9458P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4960
_refine_ls_wR_factor_ref         0.5030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12183
_reflns_number_total             14903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00433_si_002.cif
_cod_data_source_block           pentaphenylh
_cod_database_code               4034583
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.958
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14), C21(H21), C23(H23),
 C29(H29), C30(H30), C31(H31), C32(H32), C35(H35), C37(H37), C39(H39)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C41(H41A,H41B,H41C), C42(H42A,
 H42B,H42C), C43(H43A,H43B,H43C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C),
 C47(H47A,H47B,H47C)
;
_shelx_res_checksum              4694
_olex2_submission_special_instructions 'No special instructions were received'