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_7160511
_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 H19 N O6'
_chemical_formula_sum            'C21 H19 N O6'
_chemical_formula_weight         381.37
_chemical_name_systematic
'dimethyl (Z)-2-(1-benzamido-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             2024-06-28
_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                78.692(11)
_cell_angle_beta                 84.933(10)
_cell_angle_gamma                79.177(10)
_cell_formula_units_Z            2
_cell_length_a                   5.6083(15)
_cell_length_b                   12.004(4)
_cell_length_c                   14.983(5)
_cell_measurement_reflns_used    1676
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      23.02
_cell_measurement_theta_min      2.43
_cell_volume                     970.1(5)
_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      213.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1003
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11298
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.431
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6333
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1037 before and 0.0875 after correction.
The Ratio of minimum to maximum transmission is 0.8494.
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    1.306
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/PE'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0706P)^2^+0.1473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1903
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1893
_reflns_number_total             3413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00333d2.cif
_cod_data_source_block           mo_zg_zxy_1p_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160511--7160512.cif.'
_cod_database_code               7160511
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.971
_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. Uiso/Uaniso restraints and constraints
Uanis(C10A) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(O6A) \\sim Ueq, Uanis(O6)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(O6A)=1-FVAR(1)
 Sof(O6)=FVAR(1)
 Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(2)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
4.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F)
;
_shelx_res_checksum              2948
_olex2_submission_special_instructions 'No special instructions were received'