Phosphine-catalyzed fixation of CO2 with γ-hydroxyl alkynone under ambient temperature and pressure: kinetic resolution and further conversion
Sun, Yao-Liang; Wei, Yin; Shi, Min; Organic Chemistry Frontiers 6 (2019) 2420–; doi:10.1039/C9QO00642G

data_1554992
_publ_section_title
;
 Phosphine-catalyzed fixation of CO2 with \g-hydroxyl alkynone under
 ambient temperature and pressure: kinetic resolution and further
 conversion
;
_journal_issue                   14
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2420
_journal_paper_doi               10.1039/C9QO00642G
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-18 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.27760(10)
_cell_length_b                   10.8907(2)
_cell_length_c                   22.1326(4)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.911
_cell_measurement_theta_min      3.475
_cell_volume                     1272.11(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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      170.01
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13350
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.886
_diffrn_reflns_theta_min         3.475
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1784 before and 0.0553 after correction. The Ratio of minimum to maximum transmission is 0.8367. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 931 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.2934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2322
_reflns_number_total             2370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00642g2.cif
_cod_data_source_block           mjl18313_0m
_cod_database_code               1554992
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.943
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              35257
_shelx_hkl_checksum              88564
_olex2_submission_special_instructions 'No special instructions were received'