Synthesis of Sugar Diene and its Pd-catalyzed Transformation into Chromanes.
Maikhuri, Vipin Kumar; Khatri, Vinod; Kumar, Amit; Singh, Balram; Prasad, Ashok K.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00432

data_4038404
_publ_section_title
;
 Synthesis of Sugar Diene and its Pd-catalyzed Transformation into
 Chromanes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00432
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C33 H32 O9 S2'
_chemical_formula_sum            'C33 H32 O9 S2'
_chemical_formula_weight         636.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.647(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.185(5)
_cell_length_b                   5.9809(9)
_cell_length_c                   16.116(3)
_cell_measurement_reflns_used    5366
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.186
_cell_measurement_theta_min      2.162
_cell_volume                     3012.4(9)
_computing_cell_refinement       'SAINT V8.30C (?, 2016)'
_computing_data_reduction        'SAINT V8.30C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18011
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.186
_diffrn_reflns_theta_max         25.186
_diffrn_reflns_theta_min         2.162
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       needle
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5366
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0342P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4876
_reflns_number_total             5366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00432_si_001.cif
_cod_data_source_block           vg_401_0m
_cod_original_cell_volume        3012.5(8)
_cod_database_code               4038404
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C8(H8), C5(H5), C28(H28), C24(H24), C13(H13),
 C22(H22), C31(H31), C29(H29), C14(H14), C25(H25), C21(H21), C32(H32)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C1(H1A,H1B,H1C), C33(H33A,H33B,H33C)
;
_olex2_submission_special_instructions 'No special instructions were received'