Forging structural complexity: diastereoselective synthesis of densely substituted β-lactams with dual functional handles for enhanced core modifications.
Rodriguez Treviño, Agustin M; Loch-Temzelides, Pierre; Pandiri, Sanjay; Kirkland, Justin K.; Davenport, Michael T.; Aguinaga, Ulises; Yousufuddin, Muhammed; Ess, Daniel H.; Kürti, László; Chemical science 15 (2024) 14668–14676; doi:10.1039/d4sc01513d

data_1572777
_publ_section_title
;
 Forging structural complexity: diastereoselective synthesis of densely
 substituted &#x3b2;-lactams with dual functional handles for enhanced
 core modifications.
;
_journal_issue                   36
_journal_name_full               'Chemical science'
_journal_page_first              14668
_journal_page_last               14676
_journal_paper_doi               10.1039/d4sc01513d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C16 H13 Br Cl N O2'
_chemical_formula_sum            'C16 H13 Br Cl N O2'
_chemical_formula_weight         366.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-10-14 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.375(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.915(3)
_cell_length_b                   17.251(6)
_cell_length_c                   10.682(3)
_cell_measurement_reflns_used    4625
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.52
_cell_measurement_theta_min      2.27
_cell_volume                     1650.8(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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  0.0363
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20864
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.775
_diffrn_reflns_theta_min         2.347
_exptl_absorpt_coefficient_mu    2.654
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         5570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0668P)^2^+0.4672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1519
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2956
_reflns_number_total             5570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01513d2.cif
_cod_data_source_block           arc77_0m_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1572777
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.619
_shelx_estimated_absorpt_t_max   0.777
_shelx_res_checksum              30598
_shelx_hkl_checksum              93279