Open-close: an alternative strategy to α-functionalization of lactone via enamine catalysis in one pot under mild conditions.
Liu, Yan-Kai; Li, Zhi-Long; Li, Ji-Yao; Feng, Huan-Xi; Tong, Zhi-Ping; Organic letters 17 (2015) 2022–2025; doi:10.1021/acs.orglett.5b00794

data_1554990
_publ_section_title
;
 Open-close: an alternative strategy to \a-functionalization of lactone
 via enamine catalysis in one pot under mild conditions.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2022
_journal_page_last               2025
_journal_paper_doi               10.1021/acs.orglett.5b00794
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H13 N O4 S'
_chemical_formula_weight         303.32
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1609(13)
_cell_length_b                   9.0398(14)
_cell_length_c                   19.318(3)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.09
_cell_volume                     1425.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0276
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20899
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         3.086
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.553
_exptl_crystal_size_mid          0.512
_exptl_crystal_size_min          0.489
_refine_diff_density_max         1.119
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details
; 
 Flack x determined using 1213 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.09(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0806
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1598P)^2^+0.7521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2376
_refine_ls_wR_factor_ref         0.2429
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3048
_reflns_number_total             3278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00794_si_002.cif
_cod_data_source_block           1SAD
_cod_original_cell_volume        1425.2(4)
_cod_database_code               1554990
_shelx_estimated_absorpt_t_min   0.878
_shelx_estimated_absorpt_t_max   0.891
_shelxl_version_number           2013-4
_shelx_res_checksum              98283
_shelx_hkl_checksum              59130