Highly Regio- and Stereoselective Synthesis of Cyclic Carbonates from Biomass-derived Polyols via Organocatalytic Cascade Reaction
Zhou, Hui; Zhang, Hui; Mu, Sen; Zhang, Wen-Zhen; Ren, Wei-Min; Lu, Xiaobing; Green Chemistry  (2019) –; doi:10.1039/C9GC03013A

data_7234810
_publ_section_title
;
 Highly Regio- and Stereoselective Synthesis of Cyclic Carbonates from
 Biomass-derived Polyols via Organocatalytic Cascade Reaction
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/C9GC03013A
_journal_year                    2019
_chemical_formula_moiety         'C9 H8 O9'
_chemical_formula_sum            'C9 H8 O9'
_chemical_formula_weight         260.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-11 deposited with the CCDC.    2019-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.709(4)
_cell_length_b                   12.143(8)
_cell_length_c                   14.775(9)
_cell_measurement_reflns_used    1113
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.686
_cell_measurement_theta_min      2.757
_cell_volume                     1024.3(12)
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_reduction        'SAINT V8.32B (?, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6472
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.352
_diffrn_reflns_theta_min         2.171
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0539 before and 0.0456 after correction. The Ratio of minimum to maximum transmission is 0.8812. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0397P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1555
_reflns_number_total             2326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc03013a2.cif
_cod_data_source_block           19aug1a_0m
_cod_database_code               7234810
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 3(2)
 -2(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B)
;
_shelx_res_checksum              92911
_shelx_hkl_checksum              3773
_olex2_submission_special_instructions 'No special instructions were received'