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_7155075
_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         'C15 H15 N O6'
_chemical_formula_sum            'C15 H15 N O6'
_chemical_formula_weight         305.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-02
_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                90.00
_cell_angle_beta                 98.1319(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.47048(18)
_cell_length_b                   8.60587(17)
_cell_length_c                   18.2016(4)
_cell_measurement_reflns_used    5166
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9230
_cell_measurement_theta_min      4.9090
_cell_volume                     1468.55(5)
_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-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9973
_diffrn_measurement_details
;
  1 omega  -13.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000   60.0000 46

  2 omega -113.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -150.0000 102

  3 omega  -41.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -180.0000 26

  4 omega  -48.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000    0.0000 83

  5 omega   30.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 79

  6 omega   89.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 89

  7 omega   49.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 45

  8 omega  122.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 25

  9 omega   73.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 25

 10 omega   99.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 37

 11 omega  103.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 56

 12 omega   59.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 27

 13 omega  116.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 46

 14 omega   58.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 25

 15 omega   52.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 34

 16 omega   38.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 42

 17 omega  109.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 54

 18 omega   51.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 27

 19 omega   43.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 39

 20 omega   43.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 61

 21 omega   58.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1033986000
_diffrn_orient_matrix_UB_12      -0.0083330000
_diffrn_orient_matrix_UB_13      -0.0733270000
_diffrn_orient_matrix_UB_21      -0.1197007000
_diffrn_orient_matrix_UB_22      -0.0561086000
_diffrn_orient_matrix_UB_23      0.0427402000
_diffrn_orient_matrix_UB_31      -0.0445605000
_diffrn_orient_matrix_UB_32      0.1697211000
_diffrn_orient_matrix_UB_33      0.0104831000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8087
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         4.91
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87955
_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    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0407P)^2^+0.5769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                2555
_reflns_number_total             2800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00588h2.cif
_cod_data_source_block           smi4
_cod_depositor_comments
'Adding full bibliography for 7155074--7155075.cif.'
_cod_database_code               7155075
_chemical_oxdiff_formula         'C16 H15 N1 O6'
_reflns_odcompleteness_completeness 94.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95