A Thiocyanopalladation/Carbocyclization Transformation Identified Through Enzymatic Screening: Stereocontrolled Tandem C-SCN and C-C Bond Formation
Malik, Guillaume; Swyka, Robert A.; Tiwari, Virendra K.; Fei, Xiang; Applegate, Gregory A.; Berkowitz, David B.; Chem. Sci.  (2017) –; doi:10.1039/C7SC04083K

data_1547538
_publ_section_title
;
 A Thiocyanopalladation/Carbocyclization Transformation Identified Through
 Enzymatic Screening: Stereocontrolled Tandem C-SCN and C-C Bond Formation
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC04083K
_journal_year                    2017
_chemical_absolute_configuration abs
_chemical_formula_sum            'C9 H9 N O S'
_chemical_formula_weight         179.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-10-31 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.351(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8614(10)
_cell_length_b                   27.535(5)
_cell_length_c                   5.9676(10)
_cell_measurement_reflns_used    4480
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.65
_cell_measurement_theta_min      4.82
_cell_volume                     839.5(3)
_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    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker Platinum 135 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4298
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         67.649
_diffrn_reflns_theta_min         6.430
_exptl_absorpt_coefficient_mu    2.984
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       Near
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.420
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.17(4)
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0869P)^2^+0.7157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                1923
_reflns_number_total             1923
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04083k2.cif
_cod_data_source_block           v73c
_cod_original_cell_volume        839.5(2)
_cod_database_code               1547538
_shelx_estimated_absorpt_t_min   0.317
_shelx_estimated_absorpt_t_max   0.367
_shelxl_version_number           2013-4
_shelx_res_checksum              14659