Chemical and Biochemical Approaches for the Synthesis of Substituted Dihydroxybutanones and Di- and Tri-Hydroxypentanones.
Al-Smadi, Derar; Enugala, Thilak Reddy; Kessler, Vadim; Mhashal, Anil Ranu; Lynn Kamerlin, Shina Caroline; Kihlberg, Jan; Norberg, Thomas; Widersten, Mikael; The Journal of organic chemistry 84 (2019) 6982–6991; doi:10.1021/acs.joc.9b00742

data_4034577
_publ_section_title
;
 Chemical and Biochemical Approaches for the Synthesis of Substituted
 Dihydroxybutanones and Di- and Tri-Hydroxypentanones.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6982
_journal_page_last               6991
_journal_paper_doi               10.1021/acs.joc.9b00742
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C11 H13 Cl O3'
_chemical_formula_weight         228.66
_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_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.694(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.851(15)
_cell_length_b                   4.703(5)
_cell_length_c                   16.195(16)
_cell_measurement_reflns_used    2136
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      2.64
_cell_volume                     1077.6(19)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 SMART Apex2 CCD'
_diffrn_measurement_method       'Omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.993
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_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
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_diffrn_reflns_theta_min         2.229
_diffrn_source                   'sealed tube'
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_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.888
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_exptl_crystal_colour            colorless
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_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
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_exptl_crystal_size_mid          0.100
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_exptl_transmission_factor_min   0.888
_refine_diff_density_max         0.526
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_refine_ls_number_reflns         1944
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0289P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1485
_reflns_number_total             1944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00742_si_004.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Empirical' was
changed to 'empirical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1077.8(19)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034577
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.973
_exptl_absorpt_special_details   'Bruker SADABS'
_shelx_res_checksum              29863
_shelx_hkl_checksum              26676