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_7234809
_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         'C13 H16 O10'
_chemical_formula_sum            'C13 H16 O10'
_chemical_formula_weight         332.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-28 deposited with the CCDC.    2019-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.690(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.095(2)
_cell_length_b                   9.4714(14)
_cell_length_c                   11.1536(18)
_cell_measurement_reflns_used    1827
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.57
_cell_measurement_theta_min      2.61
_cell_volume                     1452.6(4)
_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      296.15
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7218
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_min         2.611
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6034
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0833 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.8094.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             696
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.020(7)
_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   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.1080
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1530P)^2^+4.2247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3398
_refine_ls_wR_factor_ref         0.3577
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2143
_reflns_number_total             3293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc03013a2.cif
_cod_data_source_block           w
_cod_database_code               7234809
_shelx_shelxl_version_number     2018/3
_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:
 C3(H3), C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              12203
_shelx_hkl_checksum              99522
_olex2_submission_special_instructions 'No special instructions were received'