Synthesis of chiral lactams by asymmetric nitrogen insertion
Hammes, Jasmin; Mañas, Clara; Pedada, Abhilash; Arnold, Marlene; Wahl, Johannes M.; Chemical Science  (2025) –; doi:10.1039/D5SC08417B

data_1576239
_publ_section_title
;
 Synthesis of chiral lactams by asymmetric nitrogen insertion
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC08417B
_journal_year                    2025
_chemical_formula_moiety         'C22 H19 Cl N O2 P'
_chemical_formula_sum            'C22 H19 Cl N O2 P'
_chemical_formula_weight         395.80
_chemical_name_systematic
;
(R,Z)-(((3-(3-chlorophenyl)cyclobutylidene)amino)oxy)diphenylphosphine oxide
;
_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_method           SHELXL-2019/3
_audit_update_record
;
2025-06-17 deposited with the CCDC.	2025-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                73.851(5)
_cell_angle_beta                 85.864(5)
_cell_angle_gamma                79.040(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2954(5)
_cell_length_b                   9.0584(5)
_cell_length_c                   13.3668(8)
_cell_measurement_reflns_used    34553
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.58
_cell_measurement_theta_min      2.50
_cell_volume                     946.99(10)
_computing_cell_refinement       'X-Area Recipe 2.0.2 (Stoe & Cie, 2020)'
_computing_data_collection       'X-Area WinXpose 2.0.28 (Stoe & Cie, 2020)'
_computing_data_reduction        'X-Area Integrate 2.5.18.0 (STOE, 2020)'
_computing_molecular_graphics    'Platon (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22786
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.409
_diffrn_reflns_theta_min         2.935
_diffrn_source                   'sealed X-ray tube, 12x0.4mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9288
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
; 
 Flack x determined using 2419 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.07(9)
_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     545
_refine_ls_number_reflns         8806
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0657
_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^)+(0.0275P)^2^+2.0121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.878
_reflns_number_gt                6632
_reflns_number_total             8806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08417b2.cif
_cod_data_source_block           6i
_cod_database_code               1576239
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              58455