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_4036993
_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         'C21 H17 Cl2 F O5'
_chemical_formula_sum            'C21 H17 Cl2 F O5'
_chemical_formula_weight         439.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_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                83.956(4)
_cell_angle_beta                 87.265(4)
_cell_angle_gamma                61.768(5)
_cell_formula_units_Z            2
_cell_length_a                   6.6638(3)
_cell_length_b                   6.7128(4)
_cell_length_c                   23.7243(11)
_cell_measurement_reflns_used    4488
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.8100
_cell_measurement_theta_min      3.4040
_cell_volume                     929.81(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -49.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4727  -57.0000   90.0000 84

  2 omega    1.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4727   57.0000    0.0000 87

  3 omega  -10.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4727   77.0000 -180.0000 99

  4 omega    7.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4727   57.0000   90.0000 81

  5 omega   20.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4727   57.0000  -90.0000 51

  6 omega  -24.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4727  -99.0000 -150.0000 85

  7 omega  -13.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4727  -99.0000   30.0000 74

  8 omega  -50.00  -32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4102   77.0000  -60.0000 18
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0146243000
_diffrn_orient_matrix_UB_12      0.0065423000
_diffrn_orient_matrix_UB_13      -0.0296766000
_diffrn_orient_matrix_UB_21      -0.1192401000
_diffrn_orient_matrix_UB_22      0.0673958000
_diffrn_orient_matrix_UB_23      0.0031786000
_diffrn_orient_matrix_UB_31      0.0127948000
_diffrn_orient_matrix_UB_32      0.0996321000
_diffrn_orient_matrix_UB_33      -0.0036186000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9916
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.590
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.9780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3273
_reflns_number_total             3660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01185_si_003.cif
_cod_data_source_block           2348
_cod_database_code               4036993
_chemical_oxdiff_formula         'C52 H94 Cl2 O14 Cl F'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.891
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.01
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              77704
_shelx_hkl_checksum              859
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'