Design and Synthesis of Diversely Substituted Azacyclic Inhibitors of Endothelin Converting Enzyme
Stephen Hanessian; Cécile Gauchet; Guillaume Charron; Julien Marin; Philippe Nakache; Journal of Organic Chemistry 71 (2006) 2760–2778; doi:10.1021/jo052649y

data_4021616
_publ_section_title
;
 Design and Synthesis of Diversely Substituted Azacyclic Inhibitors
 of Endothelin Converting Enzyme
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2760
_journal_page_last               2778
_journal_paper_doi               10.1021/jo052649y
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        'synthesized by the authors, see text'
_chemical_formula_moiety         'C16 H28 N O7 P'
_chemical_formula_sum            'C16 H28 N O7 P'
_chemical_formula_weight         377.364
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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           'SHELXL96 (Sheldrick, 1996)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.106(3)
_cell_length_b                   10.272(4)
_cell_length_c                   19.673(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      20.00
_cell_volume                     2042.2(12)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'NRC-2, NRC-2A (Ahmed et al, 1973)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       '\w/2\q scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus xray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14308
_diffrn_reflns_theta_max         69.94
_diffrn_reflns_theta_min         4.50
_diffrn_standards_decay_%        11.0
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    1.496
_exptl_absorpt_correction_T_max  0.6388
_exptl_absorpt_correction_T_min  0.5125
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'ABSORP in NRCVAX (Gabe et al, 1989)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.2273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             808.0
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       0.0178(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL96 (Sheldrick, 1996)'
_refine_ls_goodness_of_fit_all   1.041
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_restrained_S_obs      1.067
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0711P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1030
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                3587
_reflns_number_total             3868
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo052649ysi20051221_063047.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
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_cod_database_code               4021616