#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:28:20 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038094.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_4038094
loop_
_publ_author_name
'Tong, Guanghu'
'Ding, Zhengwei'
'Liu, Zhi'
'Ding, You-Song'
'Xu, Liang'
'Zhang, Hailong'
'Li, Pengfei'
_publ_section_title
;
 Total Synthesis of Prostratin, a Bioactive Tigliane Diterpenoid: Access
 to Multi-Stereocenter Cyclohexanes from a Phenol.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4813
_journal_page_last               4837
_journal_paper_doi               10.1021/acs.joc.0c00022
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C22 H30 O4'
_chemical_formula_sum            'C22 H30 O4'
_chemical_formula_weight         358.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1931(7)
_cell_length_b                   9.6450(5)
_cell_length_c                   15.7110(8)
_cell_measurement_reflns_used    8782
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.48
_cell_volume                     1979.11(18)
_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      150.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14612
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         1.559
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0363
_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/[σ²(Fo²)+(0.0488P)²+0.6807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3971
_reflns_number_total             4528
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00022_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4038084--4038097.cif.'
_cod_database_code               4038094
_shelx_shelxl_version_number     2014/7
_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.
;
_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:
 C10(H10), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C19(H19A,H19B)
2.c Me refined with riding coordinates:
 C1(H1A,H1B,H1C)
2.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C4(H4), C8(H8)
2.e X=CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
2.f Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
2.g Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.99826(9) 0.20479(12) -0.03531(7) 0.0221(2) Uani 1 1 d . . . . .
H1A H 1.0481 0.1464 -0.0592 0.033 Uiso 1 1 calc R . . . .
H1B H 0.9451 0.1462 -0.0163 0.033 Uiso 1 1 calc R . . . .
H1C H 0.9668 0.2694 -0.0795 0.033 Uiso 1 1 calc R . . . .
C2 C 0.98911(8) 0.36853(11) 0.07696(6) 0.0160(2) Uani 1 1 d . . . . .
C7 C 1.04001(7) 0.43925(11) 0.14742(6) 0.0159(2) Uani 1 1 d . . . . .
H7 H 1.1118 0.4270 0.1623 0.019 Uiso 1 1 calc R . . . .
C5 C 0.88157(7) 0.54782(10) 0.17430(6) 0.0138(2) Uani 1 1 d . . . . .
C3 C 0.88417(8) 0.38736(11) 0.05373(6) 0.0167(2) Uani 1 1 d . . . . .
H3 H 0.8484 0.3400 0.0056 0.020 Uiso 1 1 calc R . . . .
C6 C 0.98820(7) 0.52786(10) 0.19683(6) 0.0142(2) Uani 1 1 d . . . . .
C4 C 0.83255(8) 0.47705(11) 0.10240(6) 0.0161(2) Uani 1 1 d . . . . .
H4 H 0.7611 0.4906 0.0860 0.019 Uiso 1 1 calc R . . . .
C9 C 1.14425(8) 0.64291(12) 0.27250(8) 0.0235(2) Uani 1 1 d . . . . .
H9A H 1.1789 0.6279 0.2243 0.028 Uiso 1 1 calc R . . . .
H9B H 1.1782 0.6886 0.3221 0.028 Uiso 1 1 calc R . . . .
C8 C 1.04839(8) 0.60009(11) 0.27066(7) 0.0179(2) Uani 1 1 d . . . . .
H8 H 1.0161 0.6168 0.3200 0.022 Uiso 1 1 calc R . . . .
C10 C 0.82250(7) 0.64636(11) 0.22413(6) 0.0137(2) Uani 1 1 d . . . . .
H10 H 0.8742 0.6994 0.2641 0.016 Uiso 1 1 calc R . . . .
C14 C 0.74770(7) 0.57976(10) 0.27981(6) 0.01287(19) Uani 1 1 d . . . . .
C11 C 0.75432(8) 0.75408(11) 0.17071(7) 0.0177(2) Uani 1 1 d . . . . .
H11A H 0.7131 0.7099 0.1204 0.021 Uiso 1 1 calc R . . . .
H11B H 0.7964 0.8288 0.1503 0.021 Uiso 1 1 calc R . . . .
C12 C 0.68472(7) 0.81173(11) 0.23362(6) 0.0156(2) Uani 1 1 d . . . . .
H12 H 0.7088 0.9063 0.2533 0.019 Uiso 1 1 calc R . . . .
C13 C 0.69741(7) 0.71084(11) 0.31138(6) 0.0142(2) Uani 1 1 d . . . . .
H13 H 0.7425 0.7528 0.3613 0.017 Uiso 1 1 calc R . . . .
C17 C 0.73558(8) 0.42492(12) 0.41164(6) 0.0180(2) Uani 1 1 d . . . . .
C15 C 0.80337(7) 0.48661(11) 0.35107(6) 0.0153(2) Uani 1 1 d . . . . .
H15A H 0.8369 0.4099 0.3238 0.018 Uiso 1 1 calc R . . . .
H15B H 0.8579 0.5417 0.3853 0.018 Uiso 1 1 calc R . . . .
C16 C 0.68525(8) 0.30588(12) 0.39395(7) 0.0233(2) Uani 1 1 d . . . . .
H16A H 0.6443 0.2687 0.4335 0.028 Uiso 1 1 calc R . . . .
H16B H 0.6904 0.2584 0.3418 0.028 Uiso 1 1 calc R . . . .
C18 C 0.72956(9) 0.50315(13) 0.49314(7) 0.0257(2) Uani 1 1 d . . . . .
H18A H 0.6776 0.4607 0.5237 0.039 Uiso 1 1 calc GR . . . .
H18B H 0.7109 0.5998 0.4794 0.039 Uiso 1 1 calc GR . . . .
H18C H 0.7962 0.5002 0.5296 0.039 Uiso 1 1 calc GR . . . .
O4 O 0.51510(6) 0.86443(8) 0.26409(5) 0.02041(17) Uani 1 1 d . . . . .
C19 C 0.57154(8) 0.81724(11) 0.19809(7) 0.0175(2) Uani 1 1 d . . . . .
H19A H 0.5605 0.8812 0.1484 0.021 Uiso 1 1 calc R . . . .
H19B H 0.5474 0.7239 0.1783 0.021 Uiso 1 1 calc R . . . .
C21 C 0.53168(8) 0.78446(12) 0.34246(7) 0.0198(2) Uani 1 1 d . . . . .
C20 C 0.43211(9) 0.71510(14) 0.35572(10) 0.0341(3) Uani 1 1 d . . . . .
H20A H 0.4104 0.6520 0.3077 0.051 Uiso 1 1 calc GR . . . .
H20B H 0.3794 0.7859 0.3584 0.051 Uiso 1 1 calc GR . . . .
H20C H 0.4422 0.6626 0.4097 0.051 Uiso 1 1 calc GR . . . .
C22 C 0.57076(11) 0.88484(15) 0.41424(8) 0.0346(3) Uani 1 1 d . . . . .
H22A H 0.5806 0.8354 0.4693 0.052 Uiso 1 1 calc GR . . . .
H22B H 0.5208 0.9595 0.4163 0.052 Uiso 1 1 calc GR . . . .
H22C H 0.6362 0.9244 0.4034 0.052 Uiso 1 1 calc GR . . . .
O2 O 0.67502(5) 0.50251(8) 0.22356(4) 0.01508(16) Uani 1 1 d . . . . .
H2 H 0.6258 0.4804 0.2493 0.023 Uiso 1 1 calc GR . . . .
O3 O 0.60061(5) 0.67330(8) 0.33562(5) 0.01710(16) Uani 1 1 d . . . . .
O1 O 1.04889(6) 0.28112(8) 0.03608(5) 0.02107(18) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C2 C3 119.68(9) . . ?
O1 C2 C7 115.39(9) . . ?
O1 C2 C3 124.92(9) . . ?
C2 C7 C6 121.58(9) . . ?
C6 C5 C10 121.47(9) . . ?
C4 C5 C6 117.77(9) . . ?
C4 C5 C10 120.72(9) . . ?
C2 C3 C4 118.80(9) . . ?
C7 C6 C5 119.46(9) . . ?
C7 C6 C8 118.17(9) . . ?
C5 C6 C8 122.37(9) . . ?
C3 C4 C5 122.69(9) . . ?
C9 C8 C6 124.50(10) . . ?
C5 C10 C14 116.57(8) . . ?
C5 C10 C11 116.37(8) . . ?
C11 C10 C14 102.58(7) . . ?
C13 C14 C10 100.33(8) . . ?
C15 C14 C10 112.12(8) . . ?
C15 C14 C13 115.31(8) . . ?
O2 C14 C10 107.12(7) . . ?
O2 C14 C13 110.31(8) . . ?
O2 C14 C15 110.94(8) . . ?
C10 C11 C12 104.36(8) . . ?
C11 C12 C13 105.68(8) . . ?
C19 C12 C11 114.82(9) . . ?
C19 C12 C13 107.59(8) . . ?
C14 C13 C12 105.32(8) . . ?
O3 C13 C14 108.61(8) . . ?
O3 C13 C12 111.55(8) . . ?
C16 C17 C15 121.77(10) . . ?
C16 C17 C18 121.74(10) . . ?
C18 C17 C15 116.49(9) . . ?
C17 C15 C14 114.99(8) . . ?
C19 O4 C21 114.57(8) . . ?
O4 C19 C12 109.23(8) . . ?
O4 C21 C20 108.88(9) . . ?
O4 C21 C22 106.68(9) . . ?
C20 C21 C22 112.90(10) . . ?
O3 C21 O4 111.14(8) . . ?
O3 C21 C20 104.72(9) . . ?
O3 C21 C22 112.55(9) . . ?
C21 O3 C13 115.76(8) . . ?
C2 O1 C1 116.63(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4264(13) . ?
C2 C7 1.3897(14) . ?
C2 C3 1.3928(14) . ?
C2 O1 1.3743(12) . ?
C7 C6 1.3966(14) . ?
C5 C6 1.4144(13) . ?
C5 C4 1.3978(14) . ?
C5 C10 1.5153(13) . ?
C3 C4 1.3942(14) . ?
C6 C8 1.4835(14) . ?
C9 C8 1.3268(15) . ?
C10 C14 1.5478(13) . ?
C10 C11 1.5426(14) . ?
C14 C13 1.5420(14) . ?
C14 C15 1.5387(13) . ?
C14 O2 1.4198(11) . ?
C11 C12 1.5447(14) . ?
C12 C13 1.5523(14) . ?
C12 C19 1.5194(14) . ?
C13 O3 1.4299(11) . ?
C17 C15 1.5167(14) . ?
C17 C16 1.3357(16) . ?
C17 C18 1.4980(15) . ?
O4 C19 1.4337(12) . ?
O4 C21 1.4431(12) . ?
C21 C20 1.5145(16) . ?
C21 C22 1.5200(17) . ?
C21 O3 1.4197(12) . ?
