A novel strategy for the synthesis of thermally stable and apoptosis-inducing 2,3-dihydroazetes.
Smetanin, Ilia A.; Novikov, Mikhail S.; Agafonova, Anastasiya V.; Rostovskii, Nikolai V.; Khlebnikov, Alexander F.; Kudryavtsev, Igor V.; Terpilowski, Maxim A.; Serebriakova, Maria K.; Trulioff, Andrey S.; Goncharov, Nikolay V.; Organic & biomolecular chemistry 14 (2016) 4479–4487; doi:10.1039/c6ob00588h

data_7155074
_publ_section_title
;
 A novel strategy for the synthesis of thermally stable and
 apoptosis-inducing 2,3-dihydroazetes.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4479
_journal_page_last               4487
_journal_paper_doi               10.1039/c6ob00588h
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C16 H20 N O8 P'
_chemical_formula_sum            'C16 H20 N O8 P'
_chemical_formula_weight         385.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-19
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2016-01-26 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                78.735(8)
_cell_angle_beta                 81.657(7)
_cell_angle_gamma                85.426(7)
_cell_formula_units_Z            2
_cell_length_a                   8.8135(7)
_cell_length_b                   9.3935(9)
_cell_length_c                   11.2015(10)
_cell_measurement_reflns_used    4342
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.9770
_cell_measurement_theta_min      3.1290
_cell_volume                     898.61(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_measurement_details
;
  1 omega  -90.00  -64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2751 -178.0000 -120.0000 26

  2 omega  -98.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2751    0.0000  120.0000 122

  3 omega   -1.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2126   77.0000   90.0000 100

  4 omega  -10.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2126  -99.0000 -180.0000 81

  5 omega  -23.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2126  -99.0000  -30.0000 92

  6 omega   60.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2126 -178.0000  -30.0000 33

  7 omega  -93.00  -68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2751  -77.0000  -30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0625685000
_diffrn_orient_matrix_UB_12      -0.0136386000
_diffrn_orient_matrix_UB_13      0.0347037000
_diffrn_orient_matrix_UB_21      -0.0397337000
_diffrn_orient_matrix_UB_22      -0.0563337000
_diffrn_orient_matrix_UB_23      0.0412339000
_diffrn_orient_matrix_UB_31      0.0337819000
_diffrn_orient_matrix_UB_32      -0.0508446000
_diffrn_orient_matrix_UB_33      -0.0365876000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8555
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.62
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0422P)^2^+0.4440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                3510
_reflns_number_total             4127
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00588h2.cif
_cod_data_source_block           smi9
_cod_depositor_comments
'Adding full bibliography for 7155074--7155075.cif.'
_cod_original_cell_volume        898.60(14)
_cod_database_code               7155074
_chemical_oxdiff_formula         'C16 H20 N1 o8 p1'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44