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_1572778
_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         'C10 H10 Br N O2'
_chemical_formula_sum            'C10 H10 Br N O2'
_chemical_formula_weight         256.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-10-22 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6110(6)
_cell_length_b                   7.1772(8)
_cell_length_c                   25.602(3)
_cell_measurement_reflns_used    4497
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.39
_cell_volume                     1031.0(2)
_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-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0290
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            13720
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.875
_diffrn_reflns_theta_min         2.948
_exptl_absorpt_coefficient_mu    3.959
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.272(14)
_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     129
_refine_ls_number_reflns         3540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.1953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0873
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2694
_reflns_number_total             3540
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01513d2.cif
_cod_data_source_block           arc40f2_0m_a
_cod_database_code               1572778
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.505
_shelx_estimated_absorpt_t_max   0.693
_shelx_res_checksum              58498
_shelx_hkl_checksum              97638