Stereoselective Total Synthesis of (-)-(2S,4R)-3'-Methoxyl Citreochlorol: Preparation and Use of New Proline Based Auxiliary for Asymmetric Acetate Aldol Reaction.
Sunnapu, Ranganayakulu; Banoth, Saikumar Naik; R S, Reyno; Thomas, Aleena; Venugopal, Navyasree; Rajendar, Goreti; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03227

data_4037957
_publ_section_title
;
 Stereoselective Total Synthesis of (-)-(2S,4R)-3'-Methoxyl Citreochlorol:
 Preparation and Use of New Proline Based Auxiliary for Asymmetric Acetate
 Aldol Reaction.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03227
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C13 H20 Cl2 O5'
_chemical_formula_sum            'C13 H20 Cl2 O5'
_chemical_formula_weight         327.19
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.179(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.682(2)
_cell_length_b                   6.4255(14)
_cell_length_c                   26.074(6)
_cell_measurement_reflns_used    2943
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.35
_cell_measurement_theta_min      2.41
_cell_volume                     1596.6(6)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker KAPPA 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  0.0594
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21317
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         0.793
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      1.360
_exptl_crystal_density_method    NONE
_exptl_crystal_description       long-plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5629
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0805
_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^)+(0.1542P)^2^+0.6899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2178
_refine_ls_wR_factor_ref         0.2670
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3368
_reflns_number_total             5629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03227_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'RM' was changed
to 'rm' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037957
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              48875
_shelx_hkl_checksum              86275