Kinetics and Mechanism of Oxirane Formation by Darzens Condensation of Ketones: Quantification of the Electrophilicities of Ketones.
Li, Zhen; Jangra, Harish; Chen, Quan; Mayer, Peter; Ofial, Armin R.; Zipse, Hendrik; Mayr, Herbert; Journal of the American Chemical Society 140 (2018) 5500–5515; doi:10.1021/jacs.8b01657

data_4132114
_publ_section_title
;
 Kinetics and Mechanism of Oxirane Formation by Darzens Condensation of
 Ketones: Quantification of the Electrophilicities of Ketones.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5500
_journal_page_last               5515
_journal_paper_doi               10.1021/jacs.8b01657
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C13 H17 Cl O3 S'
_chemical_formula_sum            'C13 H17 Cl O3 S'
_chemical_formula_weight         288.77
_chemical_name_common            4ca
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_code                C13H17ClO3S_vv696_mayr
_audit_creation_method           'APEX3 v2017.3-0'
_audit_update_record             13-Nov-17
_cell_angle_alpha                90
_cell_angle_beta                 114.9120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6959(5)
_cell_length_b                   6.9198(2)
_cell_length_c                   21.5771(6)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      26.3842
_cell_measurement_theta_min      2.8375
_cell_volume                     2667.16(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            41776
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.157
_diffrn_source                   'rotating anode (TXS)'
_diffrn_source_current           50
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         5441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0288P)^2^+2.1533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0803
_reflns_d_resolution_high        0.8000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4562
_reflns_number_total             5441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01657_si_003.cif
_cod_data_source_block           vv696
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4132114
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              2840
_shelx_hkl_checksum              20457
_shelx_title                     ' vv696_0m_a.res in P2(1)/n'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            259.69
_shelx_f_squared_multiplier      1.000