Regiospecific syntheses of 6alpha-(1R-Hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid as mechanistic probes of class D beta-lactamases.
Testero, Sebastian A.; O'Daniel, Peter I; Shi, Qicun; Lee, Mijoon; Hesek, Dusan; Ishiwata, Akihiro; Noll, Bruce C.; Mobashery, Shahriar; Organic letters 11 (2009) 2515–2518; doi:10.1021/ol900668k

data_1503926
_publ_section_title
;
 Regiospecific syntheses of 6alpha-(1R-Hydroxyoctyl)penicillanic acid and
 6beta-(1R-hydroxyoctyl)penicillanic acid as mechanistic probes of class D
 beta-lactamases.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2515
_journal_page_last               2518
_journal_paper_doi               10.1021/ol900668k
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C21 H19 Br2 N O3 S'
_chemical_formula_sum            'C21 H19 Br2 N O3 S'
_chemical_formula_weight         525.25
_chemical_name_common            'Benzhydryl 6,6-dibromopenicillanate'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1020(3)
_cell_length_b                   12.1513(4)
_cell_length_c                   16.7878(5)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.91
_cell_measurement_theta_min      2.63
_cell_volume                     2060.74(11)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker SMART Apex CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22778
_diffrn_reflns_theta_full        69.47
_diffrn_reflns_theta_max         69.47
_diffrn_reflns_theta_min         4.49
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFCU2K-90'
_exptl_absorpt_coefficient_mu    6.125
_exptl_absorpt_correction_T_max  0.28
_exptl_absorpt_correction_T_min  0.15
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.060(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+2.0719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0763
_reflns_number_gt                3613
_reflns_number_total             3618
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900668k_si_004.cif
_cod_data_source_block           compound_1
_cod_database_code               1503926