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#$Date: 2024-10-04 12:48:11 +0300 (Fri, 04 Oct 2024) $
#$Revision: 295043 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/27/1572776.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1572776
loop_
_publ_author_name
'Rodriguez Treviño, Agustin M'
'Loch-Temzelides, Pierre'
'Pandiri, Sanjay'
'Kirkland, Justin K.'
'Davenport, Michael T.'
'Aguinaga, Ulises'
'Yousufuddin, Muhammed'
'Ess, Daniel H.'
'Kürti, László'
_publ_section_title
;
 Forging structural complexity: diastereoselective synthesis of densely
 substituted β-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 Br2 N O2'
_chemical_formula_sum            'C16 H13 Br2 N O2'
_chemical_formula_weight         411.09
_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                 115.609(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9175(14)
_cell_length_b                   17.323(3)
_cell_length_c                   10.7669(15)
_cell_measurement_reflns_used    4047
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.59
_cell_measurement_theta_min      2.28
_cell_volume                     1668.1(4)
_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 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18321
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.146
_diffrn_reflns_theta_min         2.336
_exptl_absorpt_coefficient_mu    4.862
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.068
_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         4466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0442
_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/[σ²(Fo²)+(0.0500P)²+1.3201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2755
_reflns_number_total             4466
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc01513d2.cif
_cod_data_source_block           arb208_0m_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1572776
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.323
_shelx_estimated_absorpt_t_max   0.793
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.77143(5) 0.09896(3) 0.30782(5) 0.08462(19) Uani 1 1 d . . . . .
Br2 Br 0.70147(5) 0.04921(3) 0.55557(6) 0.08555(19) Uani 1 1 d . . . . .
O1 O 0.9537(3) 0.20267(19) 0.6164(3) 0.0784(8) Uani 1 1 d . . . . .
O2 O 0.7070(3) 0.32534(14) 0.5095(3) 0.0637(7) Uani 1 1 d . . . . .
N1 N 0.7126(3) 0.24857(17) 0.4797(3) 0.0574(7) Uani 1 1 d . . . . .
C1 C 0.7183(3) 0.1338(2) 0.4502(3) 0.0499(7) Uani 1 1 d . . . . .
C2 C 0.8248(4) 0.1980(2) 0.5355(4) 0.0539(8) Uani 1 1 d . . . . .
C3 C 0.5904(4) 0.19525(19) 0.4015(3) 0.0475(7) Uani 1 1 d . . . . .
H3 H 0.549541 0.204593 0.302137 0.057 Uiso 1 1 calc R U . . .
C4 C 0.7352(6) 0.3744(2) 0.4137(4) 0.0748(12) Uani 1 1 d . . . . .
H4A H 0.656159 0.368705 0.321282 0.090 Uiso 1 1 calc R U . . .
H4B H 0.829706 0.360982 0.412744 0.090 Uiso 1 1 calc R U . . .
C5 C 0.7397(4) 0.4546(2) 0.4634(4) 0.0549(8) Uani 1 1 d . . . . .
C6 C 0.8668(5) 0.4823(3) 0.5697(4) 0.0713(11) Uani 1 1 d . . . . .
H6 H 0.950832 0.450825 0.608525 0.086 Uiso 1 1 calc R U . . .
C7 C 0.8718(7) 0.5550(3) 0.6191(6) 0.0977(16) Uani 1 1 d . . . . .
H7 H 0.959925 0.572774 0.690146 0.117 Uiso 1 1 calc R U . . .
C8 C 0.7515(8) 0.6018(3) 0.5671(6) 0.0974(17) Uani 1 1 d . . . . .
H8 H 0.755870 0.650939 0.603460 0.117 Uiso 1 1 calc R U . . .
C9 C 0.6236(7) 0.5766(3) 0.4609(6) 0.0915(15) Uani 1 1 d . . . . .
H9 H 0.540793 0.608983 0.423044 0.110 Uiso 1 1 calc R U . . .
C10 C 0.6168(5) 0.5027(3) 0.4093(4) 0.0735(11) Uani 1 1 d . . . . .
H10 H 0.528852 0.485401 0.337638 0.088 Uiso 1 1 calc R U . . .
C11 C 0.4698(3) 0.18991(18) 0.4496(3) 0.0456(7) Uani 1 1 d . . . . .
C12 C 0.4951(4) 0.2121(2) 0.5814(4) 0.0592(9) Uani 1 1 d . . . . .
H12 H 0.588515 0.230744 0.641804 0.071 Uiso 1 1 calc R U . . .
C13 C 0.3829(6) 0.2066(3) 0.6235(5) 0.0764(12) Uani 1 1 d . . . . .
H13 H 0.400287 0.222019 0.711858 0.092 Uiso 1 1 calc R U . . .
C14 C 0.2448(5) 0.1784(3) 0.5350(6) 0.0850(14) Uani 1 1 d . . . . .
H14 H 0.168840 0.174752 0.563497 0.102 Uiso 1 1 calc R U . . .
C15 C 0.2197(5) 0.1559(3) 0.4056(5) 0.0798(13) Uani 1 1 d . . . . .
H15 H 0.126786 0.136164 0.346216 0.096 Uiso 1 1 calc R U . . .
C16 C 0.3308(4) 0.1620(2) 0.3622(4) 0.0609(9) Uani 1 1 d . . . . .
H16 H 0.312025 0.147257 0.273199 0.073 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O2 C4 111.1(3) . . ?
C2 N1 O2 129.6(3) . . ?
C2 N1 C3 99.6(3) . . ?
O2 N1 C3 129.6(3) . . ?
C2 C1 C3 87.5(2) . . ?
C2 C1 Br2 114.6(2) . . ?
C3 C1 Br2 117.2(2) . . ?
C2 C1 Br1 110.5(2) . . ?
C3 C1 Br1 114.1(2) . . ?
Br2 C1 Br1 111.00(17) . . ?
O1 C2 N1 134.6(4) . . ?
O1 C2 C1 136.5(4) . . ?
N1 C2 C1 89.0(3) . . ?
N1 C3 C11 115.2(3) . . ?
N1 C3 C1 83.5(2) . . ?
C11 C3 C1 119.7(3) . . ?
N1 C3 H3 111.8 . . ?
C11 C3 H3 111.8 . . ?
C1 C3 H3 111.8 . . ?
O2 C4 C5 106.0(3) . . ?
O2 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
O2 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C6 C5 C10 117.8(4) . . ?
C6 C5 C4 120.1(4) . . ?
C10 C5 C4 122.1(4) . . ?
C7 C6 C5 121.0(5) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 121.2(5) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 119.5(5) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 119.9(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 120.6(4) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C16 C11 C12 118.8(3) . . ?
C16 C11 C3 119.9(3) . . ?
C12 C11 C3 121.3(3) . . ?
C13 C12 C11 120.3(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.1(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.922(3) . ?
Br2 C1 1.904(3) . ?
O1 C2 1.199(4) . ?
O2 N1 1.375(4) . ?
O2 C4 1.454(5) . ?
N1 C2 1.337(5) . ?
N1 C3 1.466(4) . ?
C1 C2 1.536(5) . ?
C1 C3 1.562(5) . ?
C3 C11 1.498(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.482(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.372(5) . ?
C5 C10 1.380(6) . ?
C6 C7 1.361(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.348(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.361(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.377(5) . ?
C11 C12 1.385(5) . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
