Synthesis of the Polyoxygenated Cyclohexanoid Core of Bioactive Glycosides Xylosmin and Flacourtosides E and F.
Modugu, Nagi Reddy; Mehta, Goverdhan; The Journal of organic chemistry 83 (2018) 10573–10579; doi:10.1021/acs.joc.8b01389

data_4035142
_publ_section_title
;
 Synthesis of the Polyoxygenated Cyclohexanoid Core of Bioactive
 Glycosides Xylosmin and Flacourtosides E and F.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10573
_journal_page_last               10579
_journal_paper_doi               10.1021/acs.joc.8b01389
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C24 H31 N O7'
_chemical_formula_sum            'C24 H29 N O7'
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_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6660(4)
_cell_length_b                   18.7662(7)
_cell_length_c                   12.2143(4)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.33
_cell_volume                     2261.68(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_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
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_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
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_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_min         2.332
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
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_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0629P)^2^+1.1217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3593
_reflns_number_total             5201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01389_si_001.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035142
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              98974
_shelx_hkl_checksum              18256