Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters.
Griswold, Jessica A.; Horwitz, Matthew A.; Leiva, Leslie V.; Johnson, Jeffrey S.; The Journal of organic chemistry 82 (2017) 2276–2280; doi:10.1021/acs.joc.6b03059

data_4032287
_publ_section_title
;
 Diastereoselective Organocatalytic Addition of \a-Angelica Lactone to
 \b-Halo-\a-ketoesters.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2276
_journal_page_last               2280
_journal_paper_doi               10.1021/acs.joc.6b03059
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C17 H19 Br O5'
_chemical_formula_sum            'C17 H19 Br O5'
_chemical_formula_weight         383.23
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.605(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1333(3)
_cell_length_b                   20.0738(10)
_cell_length_c                   11.9472(6)
_cell_measurement_reflns_used    6408
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.17
_cell_measurement_theta_min      4.33
_cell_volume                     1695.70(14)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16003
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.161
_diffrn_reflns_theta_min         4.335
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.506
_exptl_absorpt_correction_T_max  0.7283
_exptl_absorpt_correction_T_min  0.5545
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0963 before and 0.0578 after correction.
The Ratio of minimum to maximum transmission is 0.7614.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.171
_refine_diff_density_max         0.898
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0580P)^2^+0.4891P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2937
_reflns_number_total             3217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b03059_si_001.cif
_cod_data_source_block           x1610004
_cod_database_code               4032287
_shelx_estimated_absorpt_t_max   0.586
_shelx_estimated_absorpt_t_min   0.483
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C23(H23)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O11(H11)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-10-19
_olex2_date_sample_submission    2016-10-18
_olex2_submission_original_sample_id x1610004/MAH
_olex2_submission_special_instructions 'No special instructions were received'