#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:44:50 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179672 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/25/4512583.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4512583
loop_
_publ_author_name
'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.'
_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 λ/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/[σ²(Fo²)+(0.0657P)²+6.2012P] where P=(Fo²+2Fc²)/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 > 2σ(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
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014-3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_occupancy
O1 O 0.45328(5) 0.40589(5) 0.53176(7) 0.0226(2) Uani 1 1 d . .
O2 O 0.37916(5) 0.49928(5) 0.56411(7) 0.0257(3) Uani 1 1 d . .
O3 O 0.47110(6) 0.65490(5) 0.35370(8) 0.0287(3) Uani 1 1 d . .
H3 H 0.4834(11) 0.6201(11) 0.3769(16) 0.054(7) Uiso 1 1 d D .
O4 O 0.51406(6) 0.39752(6) 0.36422(9) 0.0328(3) Uani 1 1 d . .
H4 H 0.5165(11) 0.3752(12) 0.4040(18) 0.049(7) Uiso 1 1 d . .
C1 C 0.40622(8) 0.36176(7) 0.53157(12) 0.0296(4) Uani 1 1 d . .
H1A H 0.4038 0.3431 0.4695 0.044 Uiso 1 1 calc GR .
H1B H 0.3680 0.3811 0.5464 0.044 Uiso 1 1 calc GR .
H1C H 0.4149 0.3310 0.5787 0.044 Uiso 1 1 calc GR .
C2 C 0.34244(8) 0.54999(8) 0.58365(11) 0.0281(4) Uani 1 1 d . .
H2A H 0.3081 0.5503 0.5408 0.042 Uiso 1 1 calc GR .
H2B H 0.3658 0.5867 0.5750 0.042 Uiso 1 1 calc GR .
H2C H 0.3281 0.5478 0.6485 0.042 Uiso 1 1 calc GR .
C3 C 0.44525(7) 0.44933(7) 0.46355(10) 0.0213(3) Uani 1 1 d . .
C4 C 0.40728(7) 0.49811(7) 0.47893(10) 0.0212(3) Uani 1 1 d . .
C5 C 0.40037(7) 0.54080(7) 0.40854(11) 0.0214(3) Uani 1 1 d . .
H5 H 0.3739 0.5736 0.4176 0.026 Uiso 1 1 calc R .
C6 C 0.43247(7) 0.53538(7) 0.32400(10) 0.0213(3) Uani 1 1 d . .
C7 C 0.47189(7) 0.48812(7) 0.30947(10) 0.0227(3) Uani 1 1 d . .
C8 C 0.47668(7) 0.44459(7) 0.38013(11) 0.0234(3) Uani 1 1 d . .
C9 C 0.50913(7) 0.48162(7) 0.22156(11) 0.0253(3) Uani 1 1 d . .
H9A H 0.5479 0.4629 0.2382 0.030 Uiso 1 1 calc R .
H9B H 0.5177 0.5220 0.1961 0.030 Uiso 1 1 calc R .
C10 C 0.47893(8) 0.44390(7) 0.14483(11) 0.0267(4) Uani 1 1 d . .
H10A H 0.5104 0.4265 0.1042 0.032 Uiso 1 1 calc R .
H10B H 0.4573 0.4103 0.1749 0.032 Uiso 1 1 calc R .
C11 C 0.43494(7) 0.47884(7) 0.08335(11) 0.0259(3) Uani 1 1 d . .
H11A H 0.4196 0.4514 0.0344 0.031 Uiso 1 1 calc R .
H11B H 0.4574 0.5110 0.0511 0.031 Uiso 1 1 calc R .
C12 C 0.38034(7) 0.50773(7) 0.13361(11) 0.0230(3) Uani 1 1 d . .
H12 H 0.3706 0.4832 0.1903 0.028 Uiso 1 1 calc R .
C13 C 0.39362(7) 0.57174(7) 0.16526(10) 0.0217(3) Uani 1 1 d . .
C14 C 0.42244(6) 0.58320(7) 0.25150(11) 0.0211(3) Uani 1 1 d . .
C15 C 0.43915(7) 0.64174(7) 0.27350(10) 0.0226(3) Uani 1 1 d . .
C16 C 0.42594(7) 0.68951(7) 0.21466(11) 0.0248(3) Uani 1 1 d . .
H16 H 0.4382 0.7290 0.2301 0.030 Uiso 1 1 calc R .
C17 C 0.39457(7) 0.67814(7) 0.13326(11) 0.0254(3) Uani 1 1 d . .
H17 H 0.3837 0.7107 0.0939 0.030 Uiso 1 1 calc R .
C18 C 0.37832(7) 0.62020(7) 0.10706(11) 0.0248(3) Uani 1 1 d . .
C19 C 0.33991(9) 0.61249(8) 0.01987(12) 0.0349(4) Uani 1 1 d . .
H19A H 0.3562 0.6382 -0.0307 0.042 Uiso 1 1 calc R .
H19B H 0.2988 0.6266 0.0339 0.042 Uiso 1 1 calc R .
C20 C 0.33654(9) 0.54823(8) -0.01564(12) 0.0316(4) Uani 1 1 d . .
H20A H 0.3744 0.5374 -0.0477 0.038 Uiso 1 1 calc R .
H20B H 0.3033 0.5442 -0.0612 0.038 Uiso 1 1 calc R .
C21 C 0.32609(8) 0.50653(8) 0.06736(12) 0.0287(4) Uani 1 1 d . .
H21A H 0.3196 0.4652 0.0444 0.034 Uiso 1 1 calc R .
H21B H 0.2898 0.5193 0.1018 0.034 Uiso 1 1 calc R .
O5 O 0.45863(6) 0.70031(6) 0.53176(9) 0.0381(3) Uani 1 1 d D .
H5A H 0.480(2) 0.7336(16) 0.541(3) 0.057 Uiso 0.5 1 d DR P
H5B H 0.4545(11) 0.6918(10) 0.4703(12) 0.057 Uiso 1 1 d DR .
H5C H 0.4230(14) 0.716(2) 0.550(3) 0.057 Uiso 0.5 1 d DR P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O1 C1 112.53(11)
C4 O2 C2 116.93(12)
C15 O3 H3 106.4(15)
C8 O4 H4 115.3(19)
O1 C1 H1A 109.5
O1 C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1B 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O2 C2 H2A 109.5
O2 C2 H2B 109.5
O2 C2 H2C 109.5
H2A C2 H2B 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
O1 C3 C4 120.94(13)
C8 C3 O1 118.93(14)
C8 C3 C4 120.11(14)
O2 C4 C3 115.65(13)
O2 C4 C5 125.17(14)
C5 C4 C3 119.18(14)
C4 C5 H5 119.9
C4 C5 C6 120.12(14)
C6 C5 H5 119.9
C5 C6 C14 116.87(13)
C7 C6 C5 121.03(14)
C7 C6 C14 122.09(13)
C6 C7 C8 117.83(14)
C6 C7 C9 123.03(14)
C8 C7 C9 119.13(14)
O4 C8 C3 120.86(14)
O4 C8 C7 117.49(14)
C3 C8 C7 121.65(14)
C7 C9 H9A 108.8
C7 C9 H9B 108.8
C7 C9 C10 113.70(13)
H9A C9 H9B 107.7
C10 C9 H9A 108.8
C10 C9 H9B 108.8
C9 C10 H10A 108.7
C9 C10 H10B 108.7
H10A C10 H10B 107.6
C11 C10 C9 114.21(13)
C11 C10 H10A 108.7
C11 C10 H10B 108.7
C10 C11 H11A 108.1
C10 C11 H11B 108.1
C10 C11 C12 116.81(13)
H11A C11 H11B 107.3
C12 C11 H11A 108.1
C12 C11 H11B 108.1
C11 C12 H12 108.4
C13 C12 C11 111.85(13)
C13 C12 H12 108.4
C13 C12 C21 110.54(13)
C21 C12 C11 109.14(13)
C21 C12 H12 108.4
C14 C13 C12 121.02(13)
C18 C13 C12 119.90(14)
C18 C13 C14 119.06(14)
C13 C14 C6 122.58(14)
C15 C14 C6 118.11(14)
C15 C14 C13 119.19(14)
O3 C15 C14 121.62(14)
O3 C15 C16 116.55(14)
C16 C15 C14 121.81(14)
C15 C16 H16 120.8
C17 C16 C15 118.34(15)
C17 C16 H16 120.8
C16 C17 H17 119.1
C16 C17 C18 121.90(15)
C18 C17 H17 119.1
C13 C18 C19 122.19(15)
C17 C18 C13 119.52(14)
C17 C18 C19 118.09(14)
C18 C19 H19A 108.8
C18 C19 H19B 108.8
C18 C19 C20 113.97(14)
H19A C19 H19B 107.7
C20 C19 H19A 108.8
C20 C19 H19B 108.8
C19 C20 H20A 109.9
C19 C20 H20B 109.9
C19 C20 C21 108.97(14)
H20A C20 H20B 108.3
C21 C20 H20A 109.9
C21 C20 H20B 109.9
C12 C21 H21A 109.6
C12 C21 H21B 109.6
C20 C21 C12 110.25(14)
C20 C21 H21A 109.6
C20 C21 H21B 109.6
H21A C21 H21B 108.1
H5A O5 H5B 112(3)
H5A O5 H5C 96(5)
H5B O5 H5C 106(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4402(19)
O1 C3 1.3851(17)
O2 C2 1.4253(19)
O2 C4 1.3672(18)
O3 H3 0.89(3)
O3 C15 1.3793(18)
O4 H4 0.76(3)
O4 C8 1.361(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 C4 1.397(2)
C3 C8 1.385(2)
C4 C5 1.393(2)
C5 H5 0.9500
C5 C6 1.407(2)
C6 C7 1.389(2)
C6 C14 1.503(2)
C7 C8 1.404(2)
C7 C9 1.511(2)
C9 H9A 0.9900
C9 H9B 0.9900
C9 C10 1.536(2)
C10 H10A 0.9900
C10 H10B 0.9900
C10 C11 1.530(2)
C11 H11A 0.9900
C11 H11B 0.9900
C11 C12 1.554(2)
C12 H12 1.0000
C12 C13 1.528(2)
C12 C21 1.536(2)
C13 C14 1.411(2)
C13 C18 1.405(2)
C14 C15 1.395(2)
C15 C16 1.389(2)
C16 H16 0.9500
C16 C17 1.379(2)
C17 H17 0.9500
C17 C18 1.394(2)
C18 C19 1.520(2)
C19 H19A 0.9900
C19 H19B 0.9900
C19 C20 1.523(2)
C20 H20A 0.9900
C20 H20B 0.9900
C20 C21 1.524(2)
C21 H21A 0.9900
C21 H21B 0.9900
O5 H5A 0.892(19)
O5 H5B 0.901(16)
O5 H5C 0.907(19)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C3 C4 O2 -0.4(2)
O1 C3 C4 C5 -179.94(13)
O1 C3 C8 O4 1.2(2)
O1 C3 C8 C7 -178.01(14)
O2 C4 C5 C6 179.00(14)
O3 C15 C16 C17 179.37(14)
C1 O1 C3 C4 82.30(17)
C1 O1 C3 C8 -99.27(16)
C2 O2 C4 C3 177.01(13)
C2 O2 C4 C5 -3.5(2)
C3 C4 C5 C6 -1.5(2)
C4 C3 C8 O4 179.68(14)
C4 C3 C8 C7 0.4(2)
C4 C5 C6 C7 -0.7(2)
C4 C5 C6 C14 179.88(13)
C5 C6 C7 C8 2.7(2)
C5 C6 C7 C9 -177.58(14)
C5 C6 C14 C13 -112.37(17)
C5 C6 C14 C15 63.60(19)
C6 C7 C8 O4 178.12(14)
C6 C7 C8 C3 -2.6(2)
C6 C7 C9 C10 -91.90(18)
C6 C14 C15 O3 8.5(2)
C6 C14 C15 C16 -173.32(14)
C7 C6 C14 C13 68.2(2)
C7 C6 C14 C15 -115.80(17)
C7 C9 C10 C11 83.69(17)
C8 C3 C4 O2 -178.81(13)
C8 C3 C4 C5 1.7(2)
C8 C7 C9 C10 87.79(17)
C9 C7 C8 O4 -1.6(2)
C9 C7 C8 C3 177.69(14)
C9 C10 C11 C12 -60.85(19)
C10 C11 C12 C13 91.06(17)
C10 C11 C12 C21 -146.31(14)
C11 C12 C13 C14 -84.75(17)
C11 C12 C13 C18 93.73(17)
C11 C12 C21 C20 -67.59(17)
C12 C13 C14 C6 -10.5(2)
C12 C13 C14 C15 173.59(13)
C12 C13 C18 C17 -175.27(14)
C12 C13 C18 C19 10.0(2)
C13 C12 C21 C20 55.83(17)
C13 C14 C15 O3 -175.43(13)
C13 C14 C15 C16 2.8(2)
C13 C18 C19 C20 -18.5(2)
C14 C6 C7 C8 -177.90(14)
C14 C6 C7 C9 1.8(2)
C14 C13 C18 C17 3.2(2)
C14 C13 C18 C19 -171.51(15)
C14 C15 C16 C17 1.1(2)
C15 C16 C17 C18 -2.8(2)
C16 C17 C18 C13 0.7(2)
C16 C17 C18 C19 175.62(16)
C17 C18 C19 C20 166.65(16)
C18 C13 C14 C6 171.02(14)
C18 C13 C14 C15 -4.9(2)
C18 C19 C20 C21 45.0(2)
C19 C20 C21 C12 -65.20(18)
C21 C12 C13 C14 153.41(14)
C21 C12 C13 C18 -28.11(19)
