Non-natural macrocyclic inhibitors of histone deacetylases: design, synthesis, and activity.
Auzzas, Luciana; Larsson, Andreas; Matera, Riccardo; Baraldi, Annamaria; Deschênes-Simard, Benoît; Giannini, Giuseppe; Cabri, Walter; Battistuzzi, Gianfranco; Gallo, Grazia; Ciacci, Andrea; Vesci, Loredana; Pisano, Claudio; Hanessian, Stephen; Journal of medicinal chemistry 53 (2010) 8387–8399; doi:10.1021/jm101092u

data_1502670
_publ_section_title
;
 Non-natural macrocyclic inhibitors of histone deacetylases: design,
 synthesis, and activity.
;
_journal_issue                   23
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              8387
_journal_page_last               8399
_journal_paper_doi               10.1021/jm101092u
_journal_volume                  53
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         '2(C26 H31 N O6), C H4 O'
_chemical_formula_sum            'C26.5 H33 N O6.5'
_chemical_formula_weight         469.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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
_cell_angle_beta                 92.234(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1805(1)
_cell_length_b                   17.2642(4)
_cell_length_c                   28.1040(6)
_cell_measurement_reflns_used    10900
_cell_measurement_temperature    170
_cell_measurement_theta_max      62.48
_cell_measurement_theta_min      3.00
_cell_volume                     2511.63(9)
_computing_cell_refinement       'SAINT V7.60A(Bruker AXS, 2008)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.60A(Bruker AXS, 2008)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17480
_diffrn_reflns_theta_full        63.68
_diffrn_reflns_theta_max         63.68
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  0.9035
_exptl_absorpt_correction_T_min  0.7869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), 1909 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.22(17)
_refine_ls_extinction_coef       0.00069(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     664
_refine_ls_number_reflns         6164
_refine_ls_number_restraints     76
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0453P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                4667
_reflns_number_total             6164
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jm101092u_si_003.cif
_cod_data_source_block           benit8
_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 2.4.2 from
2011-04-26.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (74
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26 (92
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26 (112 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

 Adding full bibliography for 1502670.cif.
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1502670