Synthesis, stereochemical analysis, and derivatization of myricanol provide new probes that promote autophagic tau clearance.
Martin, Mackenzie D.; Calcul, Laurent; Smith, Courtney; Jinwal, Umesh K.; Fontaine, Sarah N.; Darling, April; Seeley, Kent; Wojtas, Lukasz; Narayan, Malathi; Gestwicki, Jason E.; Smith, Garry R.; Reitz, Allen B.; Baker, Bill J.; Dickey, Chad A.; ACS chemical biology 10 (2015) 1099–1109; doi:10.1021/cb501013w

data_4512583
_publ_section_title
;
 Synthesis, stereochemical analysis, and derivatization of myricanol
 provide new probes that promote autophagic tau clearance.
;
_journal_issue                   4
_journal_name_full               'ACS chemical biology'
_journal_page_first              1099
_journal_page_last               1109
_journal_paper_doi               10.1021/cb501013w
_journal_volume                  10
_journal_year                    2015
_chemical_formula_moiety         'C21 H24 O4, H2 O'
_chemical_formula_sum            'C21 H26 O5'
_chemical_formula_weight         358.42
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.3255(10)
_cell_length_b                   22.3255(10)
_cell_length_c                   14.2555(7)
_cell_measurement_reflns_used    7963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.71
_cell_measurement_theta_min      2.80
_cell_volume                     7105.3(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21368
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.669
_diffrn_reflns_theta_min         3.679
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1612 before and 0.0778 after correction.
The Ratio of minimum to maximum transmission is 0.7671.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             3072
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3529
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0657P)^2^+6.2012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3026
_reflns_number_total             3529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cb501013w_si_007.cif
_cod_data_source_block           myr_r16_6_0m
_cod_depositor_comments
'Adding full bibliography for 4512581--4512583.cif.'
_cod_original_cell_volume        7105.3(7)
_cod_database_code               4512583
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.874
_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,H,H) groups
2. Restrained distances
 O5-H5B = O5-H5A = O5-H5C
 0.88 with sigma of 0.02
 H3-H5B
 -2.2 with sigma of 0.02
3. Others
 Fixed Sof: H5A(0.5) H5C(0.5)
4.a Ternary CH refined with riding coordinates:
 C12(H12)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C16(H16), C17(H17)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              30677
_shelx_hkl_checksum              25813
_olex2_submission_special_instructions 'No special instructions were received'