#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:28:20 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038093.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_4038093
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         'C15 H20 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_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
_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                 101.1800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8382(5)
_cell_length_b                   16.7731(11)
_cell_length_c                   9.7678(6)
_cell_measurement_reflns_used    9550
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.43
_cell_volume                     1259.81(14)
_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      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0156
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16098
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.429
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.332
_exptl_crystal_size_min          0.159
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0537P)²+0.5172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2651
_reflns_number_total             2896
_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               4038093
_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:
 C2(H2A), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e 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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O -0.10031(9) 0.12811(4) 0.31586(7) 0.01308(17) Uani 1 1 d . . . . .
O2 O -0.04478(9) 0.21001(5) -0.01037(7) 0.01482(17) Uani 1 1 d . . . . .
H2 H 0.0429 0.2032 -0.0467 0.022 Uiso 1 1 calc GR . . . .
O3 O -0.23521(10) 0.33079(5) 0.39209(8) 0.01848(18) Uani 1 1 d . . . . .
C1 C 0.22948(13) 0.30309(6) 0.15112(11) 0.0160(2) Uani 1 1 d . . . . .
H1A H 0.1793 0.3297 0.0632 0.024 Uiso 1 1 calc GR . . . .
H1B H 0.3079 0.2605 0.1330 0.024 Uiso 1 1 calc GR . . . .
H1C H 0.2947 0.3419 0.2159 0.024 Uiso 1 1 calc GR . . . .
C2 C 0.08300(12) 0.26717(6) 0.21568(10) 0.0116(2) Uani 1 1 d . . . . .
H2A H 0.1335 0.2507 0.3136 0.014 Uiso 1 1 calc R . . . .
C3 C -0.05321(13) 0.33294(6) 0.22122(11) 0.0140(2) Uani 1 1 d . . . . .
H3A H 0.0033 0.3788 0.2758 0.017 Uiso 1 1 calc R . . . .
H3B H -0.1013 0.3517 0.1254 0.017 Uiso 1 1 calc R . . . .
C4 C -0.19782(13) 0.30209(6) 0.28701(11) 0.0135(2) Uani 1 1 d . . . . .
C5 C -0.29278(13) 0.23230(6) 0.21213(11) 0.0160(2) Uani 1 1 d . . . . .
H5A H -0.3623 0.2506 0.1220 0.019 Uiso 1 1 calc R . . . .
H5B H -0.3742 0.2107 0.2686 0.019 Uiso 1 1 calc R . . . .
C6 C -0.16997(13) 0.16601(6) 0.18465(10) 0.0120(2) Uani 1 1 d . . . . .
C7 C -0.00037(12) 0.19292(6) 0.13550(10) 0.0110(2) Uani 1 1 d . . . . .
C8 C 0.10952(13) 0.11528(6) 0.16986(10) 0.0118(2) Uani 1 1 d . . . . .
H8 H 0.0974 0.0826 0.0829 0.014 Uiso 1 1 calc R . . . .
C9 C 0.30364(13) 0.11848(6) 0.23967(11) 0.0155(2) Uani 1 1 d . . . . .
H9A H 0.3788 0.1147 0.1693 0.019 Uiso 1 1 calc R . . . .
H9B H 0.3312 0.1683 0.2937 0.019 Uiso 1 1 calc R . . . .
C10 C 0.32702(14) 0.04556(7) 0.33606(12) 0.0201(2) Uani 1 1 d . . . . .
H10A H 0.4334 0.0504 0.4091 0.024 Uiso 1 1 calc R . . . .
H10B H 0.3332 -0.0042 0.2827 0.024 Uiso 1 1 calc R . . . .
C11 C 0.16288(14) 0.04749(7) 0.39973(11) 0.0183(2) Uani 1 1 d . . . . .
H11A H 0.1405 -0.0053 0.4381 0.022 Uiso 1 1 calc R . . . .
H11B H 0.1734 0.0878 0.4749 0.022 Uiso 1 1 calc R . . . .
C12 C 0.01885(13) 0.06984(6) 0.27660(10) 0.0131(2) Uani 1 1 d . . . . .
C13 C -0.08909(14) -0.00115(6) 0.21124(11) 0.0165(2) Uani 1 1 d . . . . .
H13A H -0.0150 -0.0379 0.1690 0.020 Uiso 1 1 calc R . . . .
H13B H -0.1350 -0.0306 0.2841 0.020 Uiso 1 1 calc R . . . .
C14 C -0.23745(14) 0.02779(7) 0.10105(11) 0.0168(2) Uani 1 1 d . . . . .
H14 H -0.3077 -0.0096 0.0423 0.020 Uiso 1 1 calc R . . . .
C15 C -0.27106(13) 0.10527(6) 0.08521(11) 0.0150(2) Uani 1 1 d . . . . .
H15 H -0.3595 0.1229 0.0107 0.018 Uiso 1 1 calc R . . . .
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
C6 O1 C12 102.37(7) . . ?
C1 C2 C3 108.13(8) . . ?
C1 C2 C7 112.58(8) . . ?
C3 C2 C7 111.47(8) . . ?
C4 C3 C2 110.73(8) . . ?
O3 C4 C3 123.34(9) . . ?
O3 C4 C5 122.75(9) . . ?
C3 C4 C5 113.91(9) . . ?
C4 C5 C6 112.57(8) . . ?
O1 C6 C5 107.94(8) . . ?
O1 C6 C7 101.67(7) . . ?
O1 C6 C15 109.48(8) . . ?
C5 C6 C7 116.46(8) . . ?
C15 C6 C5 109.38(8) . . ?
C15 C6 C7 111.46(8) . . ?
O2 C7 C2 109.92(8) . . ?
O2 C7 C6 107.86(8) . . ?
O2 C7 C8 113.54(8) . . ?
C2 C7 C6 112.18(8) . . ?
C2 C7 C8 113.66(8) . . ?
C8 C7 C6 99.18(7) . . ?
C7 C8 C12 104.24(7) . . ?
C9 C8 C7 121.44(8) . . ?
C9 C8 C12 104.96(8) . . ?
C10 C9 C8 103.53(8) . . ?
C9 C10 C11 102.85(8) . . ?
C12 C11 C10 103.64(8) . . ?
O1 C12 C8 104.22(7) . . ?
O1 C12 C11 111.82(8) . . ?
O1 C12 C13 107.59(8) . . ?
C11 C12 C8 106.35(8) . . ?
C13 C12 C8 112.75(8) . . ?
C13 C12 C11 113.75(9) . . ?
C14 C13 C12 109.67(8) . . ?
C15 C14 C13 120.48(9) . . ?
C14 C15 C6 120.93(10) . . ?
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
O1 C6 1.4400(12) . ?
O1 C12 1.4538(12) . ?
O2 C7 1.4287(11) . ?
O3 C4 1.2197(13) . ?
C1 C2 1.5361(13) . ?
C2 C3 1.5435(13) . ?
C2 C7 1.5469(13) . ?
C3 C4 1.4993(14) . ?
C4 C5 1.4994(14) . ?
C5 C6 1.5282(13) . ?
C6 C7 1.5649(13) . ?
C6 C15 1.5201(14) . ?
C7 C8 1.5615(13) . ?
C8 C9 1.5430(14) . ?
C8 C12 1.5686(13) . ?
C9 C10 1.5326(15) . ?
C10 C11 1.5341(16) . ?
C11 C12 1.5280(14) . ?
C12 C13 1.5270(14) . ?
C13 C14 1.5037(15) . ?
C14 C15 1.3291(16) . ?
