Silver(I)-Promoted Cascade Reaction of Propargylic Alcohols, Carbon Dioxide, and Vicinal Diols: Thermodynamically Favorable Route to Cyclic Carbonates.
Zhou, Zhi-Hua; Song, Qing-Wen; He, Liang-Nian; ACS omega 2 (2017) 337–345; doi:10.1021/acsomega.6b00407

data_4516830
_publ_section_title
;
 Silver(I)-Promoted Cascade Reaction of Propargylic Alcohols, Carbon
 Dioxide, and Vicinal Diols: Thermodynamically Favorable Route to Cyclic
 Carbonates.
;
_journal_issue                   1
_journal_name_full               'ACS omega'
_journal_page_first              337
_journal_page_last               345
_journal_paper_doi               10.1021/acsomega.6b00407
_journal_volume                  2
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H30 O3'
_chemical_formula_sum            'C21 H30 O3'
_chemical_formula_weight         330.45
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-12-16
_audit_creation_method
; 
Olex2 1.2 
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103) 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.08329(7)
_cell_length_b                   10.36929(11)
_cell_length_c                   28.0962(3)
_cell_measurement_reflns_used    12438
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      78.9710
_cell_measurement_theta_min      3.2460
_cell_volume                     1772.29(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      173.15
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.184
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
; 
List of Runs (angles in degrees, time in seconds): 
  
  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames 
-------------------------------------------------------------------------- 
  1  \w   -119.00 -29.00   1.00    3.00    --  -35.00 -44.00-180.00   90 
  2  \w    -50.00  40.00   1.00    3.00    --  -35.00  72.00-180.00   90 
  3  \w   -125.00 -33.00   1.00    3.00    --  -35.00 -72.00 -72.00   92 
  4  \w   -123.00 -33.00   1.00    3.00    --  -35.00 -15.00-180.00   90 
  5  \w   -125.00 -32.00   1.00   12.00    -- -110.00  43.00-108.00   93 
  6  \w   -200.00-110.00   1.00   12.00    -- -110.00 -72.00 108.00   90 
  7  \w   -187.00 -97.00   1.00   12.00    -- -110.00 -44.00 144.00   90 
  8  \w   -113.00 -20.00   1.00   12.00    -- -110.00  72.00-108.00   93 
  9  \w   -198.00-105.00   1.00   12.00    -- -110.00 -15.00  36.00   93 
 10  \w   -119.00 -29.00   1.00   12.00    -- -110.00  72.00-180.00   90 
 11  \w   -200.00-110.00   1.00   12.00    -- -110.00 -72.00-144.00   90 
 12  \w   -200.00-110.00   1.00   12.00    -- -110.00 -72.00   0.00   90 
 13  \w   -125.00 -33.00   1.00   12.00    -- -110.00  72.00-144.00   92 
 14  \w   -125.00 -35.00   1.00   12.00    -- -110.00  72.00 -72.00   90 
;
_diffrn_measurement_device       'Rigaku XtaLAB P200 diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1704356000
_diffrn_orient_matrix_UB_12      -0.1055366000
_diffrn_orient_matrix_UB_13      -0.0113547000
_diffrn_orient_matrix_UB_21      0.1828647000
_diffrn_orient_matrix_UB_22      0.1027816000
_diffrn_orient_matrix_UB_23      -0.0015416000
_diffrn_orient_matrix_UB_31      0.0416624000
_diffrn_orient_matrix_UB_32      -0.0192979000
_diffrn_orient_matrix_UB_33      0.0535801000
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14184
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.271
_diffrn_reflns_theta_min         3.146
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Rigaku MM007HF (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
; 
 Flack x determined using 1514 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_coef       0.0060(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.4130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                3744
_reflns_number_total             3774
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao6b00407_si_001.cif
_cod_data_source_block           p20151214a
_cod_database_code               4516830
_chemical_oxdiff_formula         C21H30O3
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.842
_reflns_odcompleteness_completeness 98.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     79.02
_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: 
 C9(H9), C14(H14), C8(H8) 
2.b Secondary CH2 refined with riding coordinates: 
 C12(H12A,H12B), C11(H11A,H11B), C7(H7A,H7B), C1(H1A,H1B), C6(H6A,H6B), 
 C15(H15A,H15B), C16(H16A,H16B), C2(H2A,H2B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C4(H4) 
2.d Idealised Me refined as rotating group: 
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C) 
;
_shelx_res_checksum              88851
_shelx_hkl_checksum              35540
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
; 
Empirical correction (ABSPACK) includes: 
- Absorption correction using spherical harmonics 
- Frame scaling 
- Detector area scaling 
;
_oxdiff_exptl_absorpt_empirical_full_max 1.792
_oxdiff_exptl_absorpt_empirical_full_min 0.702