Expansion of Thiele's Acid Chemistry in Pursuit of a Suite of Conformationally Constrained Scaffolds.
Chen, Jun; Kilpatrick, Brenden; Oliver, Allen G.; Wulff, Jeremy E.; The Journal of organic chemistry 80 (2015) 8979–8989; doi:10.1021/acs.joc.5b01332

data_4036261
_publ_section_title
;
 Expansion of Thiele's Acid Chemistry in Pursuit of a Suite of
 Conformationally Constrained Scaffolds.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8979
_journal_page_last               8989
_journal_paper_doi               10.1021/acs.joc.5b01332
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H16 O4'
_chemical_formula_sum            'C14 H16 O4'
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_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.954(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5158(7)
_cell_length_b                   6.0532(5)
_cell_length_c                   11.8232(10)
_cell_measurement_reflns_used    5729
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.84
_cell_measurement_theta_min      5.23
_cell_volume                     606.17(9)
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_collection       'Bruker APEX-II v2014-11.0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15713
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.099
_diffrn_reflns_theta_min         5.222
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9075
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 1065 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         2257
_refine_ls_number_restraints     305
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1006P)^2^+0.0949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.952
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                2223
_reflns_number_total             2257
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01332_si_002.cif
_cod_data_source_block           uvic1521a
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               4036261
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.816
_shelx_estimated_absorpt_t_max   0.930
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              84179
_shelx_hkl_checksum              34077