Enantioselective insertion of vinyl diazoacetates into O–H bonds of carboxylic acids
Chen, Jiawei; Shao, Ying; Tang, Shengbiao; Sun, Jiangtao; New Journal of Chemistry 48 (2024) 5092–5096; doi:10.1039/D4NJ00289J

data_7063077
_publ_section_title
;
 Enantioselective insertion of vinyl diazoacetates into O--H bonds of
 carboxylic acids
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5092
_journal_page_last               5096
_journal_paper_doi               10.1039/D4NJ00289J
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H22 O4'
_chemical_formula_sum            'C21 H22 O4'
_chemical_formula_weight         338.38
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-10 deposited with the CCDC.	2024-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.0640(10)
_cell_angle_beta                 93.1930(10)
_cell_angle_gamma                92.5580(10)
_cell_formula_units_Z            3
_cell_length_a                   5.95320(10)
_cell_length_b                   10.2293(2)
_cell_length_c                   22.7669(4)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      54.938
_cell_measurement_theta_min      3.764
_cell_volume                     1382.90(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      213.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            43148
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.990
_diffrn_reflns_theta_min         3.383
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1527 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.6566.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 4617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         10370
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0423P)^2^+0.0950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.976
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                9902
_reflns_number_total             10370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00289j2.cif
_cod_data_source_block           230412sjt
_cod_depositor_comments          'Adding full bibliography for 7063077.cif.'
_cod_database_code               7063077
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C23(H23), C44(H44)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C26(H26), C28(H28), C27(H27), C29(H29),
  C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37),
 C38(H38), C47(H47), C48(H48), C56(H56), C49(H49), C50(H50), C51(H51), C52(H52),
  C53(H53), C55(H55), C57(H57), C58(H58), C59(H59)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C40(H40A,H40B,
 H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C61(H61A,H61B,H61C), C62(H62A,
 H62B,H62C), C63(H63A,H63B,H63C)
;
_shelx_res_checksum              78473
_olex2_submission_special_instructions 'No special instructions were received'