An Efficient Approach to Chiral C8/C9-Piperazino-Substituted 1,4-Benzodiazepin-2-ones as Peptidomimetic Scaffolds
Stefania Butini; Emanuele Gabellieri; Paul Brady Huleatt; Giuseppe Campiani; Silvia Franceschini; Margherita Brindisi; Sindu Ros; Salvatore Sanna Coccone; Isabella Fiorini; Ettore Novellino; Gianluca Giorgi; Sandra Gemma; Journal of Organic Chemistry 73 (2008) 8458–8468; doi:10.1021/jo8015456

data_4023816
_publ_contact_author_address
; Dipartimento di Chimica,
  Universit\`a degli Studi di Siena
  Via Aldo Moro
  I-53100 Siena
  Italy
;
_publ_contact_author_email       gianluca.giorgi@unisi.it
_publ_contact_author_fax         '+39 0577 234241'
_publ_contact_author_name        'Gianluca Giorgi, Ph. D.'
_publ_contact_author_phone       '+39 0577 234233'
_publ_section_title
;
 An Efficient Approach to Chiral C8/C9-Piperazino-Substituted
 1,4-Benzodiazepin-2-ones as Peptidomimetic Scaffolds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8458
_journal_page_last               8468
_journal_paper_doi               10.1021/jo8015456
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C13 H8 Cl N O4'
_chemical_formula_sum            'C13 H8 Cl N O4'
_chemical_formula_weight         277.65
_chemical_name_systematic
;
phenyl 4-chloro-2-nitrobenzoate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 107.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2110(8)
_cell_length_b                   11.8570(10)
_cell_length_c                   13.6090(12)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.4
_cell_measurement_theta_min      3.2
_cell_volume                     1263.8(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2680
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        3.2
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.020
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+0.2983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0629
_reflns_number_gt                1878
_reflns_number_total             2018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8015456_si_002.cif
_cod_data_source_block           260405
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4023816