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_4036992
_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         'C17 H26 O5'
_chemical_formula_sum            'C17 H26 O5'
_chemical_formula_weight         310.38
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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                90.00
_cell_angle_beta                 91.379(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8737(8)
_cell_length_b                   11.5374(7)
_cell_length_c                   12.6318(9)
_cell_measurement_reflns_used    4689
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.1643
_cell_measurement_theta_min      2.3863
_cell_volume                     1584.25(19)
_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
_diffrn_detector_area_resol_mean 16.0560
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -53.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6208    0.0000 -180.0000 139

  2 omega  -29.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6208  -52.0000  153.0000 67

  3 omega   61.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6208  179.0000    0.0000 32

  4 omega  -82.00  -32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0270  179.0000 -120.0000 50

  5 omega  -89.00   -3.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0270  -52.0000  153.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0018105000
_diffrn_orient_matrix_UB_12      0.0553003000
_diffrn_orient_matrix_UB_13      -0.0244905000
_diffrn_orient_matrix_UB_21      -0.0549594000
_diffrn_orient_matrix_UB_22      0.0156983000
_diffrn_orient_matrix_UB_23      0.0255244000
_diffrn_orient_matrix_UB_31      0.0350745000
_diffrn_orient_matrix_UB_32      0.0217705000
_diffrn_orient_matrix_UB_33      0.0436680000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11788
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.39
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94396
_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    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0306P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0739
_reflns_number_gt                2356
_reflns_number_total             3431
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01185_si_002.cif
_cod_data_source_block           2143
_cod_database_code               4036992
_reflns_odcompleteness_completeness 99.91
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'