Synthesis of an Iridoid-Inspired Compound Collection and Discovery of Autophagy Inhibitors.
Schröder, Peter; Bauer, Jonathan O.; Strohmann, Carsten; Kumar, Kamal; Waldmann, Herbert; The Journal of organic chemistry 81 (2016) 10242–10255; doi:10.1021/acs.joc.6b01185

data_4036994
_publ_section_title
;
 Synthesis of an Iridoid-Inspired Compound Collection and Discovery of
 Autophagy Inhibitors.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10242
_journal_page_last               10255
_journal_paper_doi               10.1021/acs.joc.6b01185
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C13 H22 O4'
_chemical_formula_sum            'C13 H22 O4'
_chemical_formula_weight         242.30
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.436(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8789(5)
_cell_length_b                   11.4732(7)
_cell_length_c                   12.3178(7)
_cell_measurement_reflns_used    4834
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.1396
_cell_measurement_theta_min      2.2892
_cell_volume                     1254.77(13)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 16.0560
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   -5.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6208   38.0000 -120.0000 84

  2 omega    8.00   34.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6208   77.0000   30.0000 26

  3 omega  -17.00   25.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6208   87.0000 -175.0000 42

  4 omega   44.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6208   38.0000  150.0000 46

  5 omega  -12.00   87.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6208   77.0000  -60.0000 99

  6 omega  -47.00   48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0270   77.0000   60.0000 95

  7 omega   34.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6208  179.0000   60.0000 50

  8 omega  -55.00   43.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6208  -38.0000 -180.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0142119000
_diffrn_orient_matrix_UB_12      0.0518590000
_diffrn_orient_matrix_UB_13      0.0297227000
_diffrn_orient_matrix_UB_21      0.0348331000
_diffrn_orient_matrix_UB_22      -0.0331076000
_diffrn_orient_matrix_UB_23      0.0418709000
_diffrn_orient_matrix_UB_31      0.0704574000
_diffrn_orient_matrix_UB_32      0.0059134000
_diffrn_orient_matrix_UB_33      -0.0261176000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12499
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.426
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0531P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1727
_reflns_number_total             2459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01185_si_001.cif
_cod_data_source_block           1922
_cod_database_code               4036994
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C10(H10A,H10B), C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              56330
_shelx_hkl_checksum              88624
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'