Hydrogen-bonding-controlled stereospecific synthesis of <i>Z</i>-enamides.
Zhang, Xiaoyu; Lu, Xiangyu; Zou, Yajun; Lang, JiaJia; Wang, Yingwei; Zhao, Gang; Organic & biomolecular chemistry 23 (2025) 4884–4887; doi:10.1039/d5ob00333d

data_7160512
_publ_section_title
;
 Hydrogen-bonding-controlled stereospecific synthesis of
 <i>Z</i>-enamides.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4884
_journal_page_last               4887
_journal_paper_doi               10.1039/d5ob00333d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C21 H18 F N O6'
_chemical_formula_sum            'C21 H18 F N O6'
_chemical_formula_weight         399.36
_chemical_name_systematic
'dimethyl (E)-2-(1-(2-fluorobenzamido)-2-oxo-2-phenylethylidene)succinate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2024-06-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-11-12 deposited with the CCDC.	2025-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                98.407(9)
_cell_angle_beta                 109.822(8)
_cell_angle_gamma                107.406(9)
_cell_formula_units_Z            2
_cell_length_a                   9.242(3)
_cell_length_b                   10.902(4)
_cell_length_c                   11.076(4)
_cell_measurement_reflns_used    4552
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      25.732
_cell_measurement_theta_min      2.449
_cell_volume                     962.9(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      303.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18300
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.033
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1604 before and 0.0855 after correction.
The Ratio of minimum to maximum transmission is 0.5903.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'white powder'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0699
_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^)+(0.1088P)^2^+0.1505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.2267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2266
_reflns_number_total             4317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00333d2.cif
_cod_data_source_block           mo_0166_4p_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160511--7160512.cif.'
_cod_original_cell_volume        963.0(5)
_cod_database_code               7160512
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C9(H9), C10(H10), C11(H11), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'