#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:28:20 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038096.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_4038096
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         'C7 H12 O3'
_chemical_formula_sum            'C7 H12 O3'
_chemical_formula_weight         144.17
_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
_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                92.7660(10)
_cell_angle_beta                 105.4420(10)
_cell_angle_gamma                108.0260(10)
_cell_formula_units_Z            2
_cell_length_a                   5.9092(7)
_cell_length_b                   7.1583(9)
_cell_length_c                   9.1902(11)
_cell_measurement_reflns_used    4206
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.32
_cell_volume                     352.68(7)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_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  0.0133
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4724
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.654
_diffrn_reflns_theta_min         2.323
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0339
_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)+(0.0456P)²+0.1468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1578
_reflns_number_total             1627
_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               4038096
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 1.22449(13) 1.08604(10) 0.32308(8) 0.01431(18) Uani 1 1 d . . . . .
H1 H 1.3446 1.1820 0.3164 0.021 Uiso 1 1 calc GR . . . .
O2 O 0.99687(12) 0.74402(10) 0.50951(8) 0.01297(17) Uani 1 1 d . . . . .
H2 H 0.9465 0.8038 0.5683 0.019 Uiso 1 1 calc GR . . . .
O3 O 0.64184(13) 0.37519(10) 0.30711(8) 0.01469(18) Uani 1 1 d . . . . .
H3 H 0.7610 0.3762 0.3817 0.022 Uiso 1 1 calc GR . . . .
C1 C 0.61241(17) 0.56588(14) 0.31227(11) 0.0134(2) Uani 1 1 d . . . . .
H1A H 0.5233 0.5773 0.3877 0.016 Uiso 1 1 calc R . . . .
H1B H 0.5074 0.5761 0.2113 0.016 Uiso 1 1 calc R . . . .
C2 C 0.85747(17) 0.73828(13) 0.35416(10) 0.0106(2) Uani 1 1 d . . . . .
H2A H 0.8203 0.8650 0.3441 0.013 Uiso 1 1 calc R . . . .
C3 C 1.02175(17) 0.72445(13) 0.25489(10) 0.0101(2) Uani 1 1 d . . . . .
H3A H 1.0699 0.6038 0.2749 0.012 Uiso 1 1 calc R . . . .
C4 C 1.26492(17) 0.90209(13) 0.28784(11) 0.0108(2) Uani 1 1 d . . . . .
H4 H 1.4015 0.8835 0.3709 0.013 Uiso 1 1 calc R . . . .
C5 C 1.32016(19) 0.89849(14) 0.13652(11) 0.0143(2) Uani 1 1 d . . . . .
H5 H 1.4788 0.9624 0.1235 0.017 Uiso 1 1 calc R . . . .
C6 C 1.1180(2) 0.79435(15) 0.02398(11) 0.0164(2) Uani 1 1 d . . . . .
H6 H 1.1128 0.7797 -0.0803 0.020 Uiso 1 1 calc R . . . .
C7 C 0.89779(18) 0.70235(14) 0.08145(11) 0.0145(2) Uani 1 1 d . . . . .
H7A H 0.8116 0.5611 0.0368 0.017 Uiso 1 1 calc R . . . .
H7B H 0.7773 0.7748 0.0583 0.017 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
O3 C1 C2 113.77(7) . . ?
O2 C2 C1 109.75(7) . . ?
O2 C2 C3 107.44(7) . . ?
C3 C2 C1 113.29(8) . . ?
C2 C3 C4 114.84(8) . . ?
C2 C3 C7 115.32(8) . . ?
C4 C3 C7 104.83(7) . . ?
O1 C4 C3 110.88(7) . . ?
O1 C4 C5 109.37(7) . . ?
C5 C4 C3 102.14(7) . . ?
C6 C5 C4 111.27(9) . . ?
C5 C6 C7 112.00(9) . . ?
C6 C7 C3 102.23(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
O1 C4 1.4459(11) . ?
O2 C2 1.4372(11) . ?
O3 C1 1.4286(11) . ?
C1 C2 1.5230(12) . ?
C2 C3 1.5188(13) . ?
C3 C4 1.5407(12) . ?
C3 C7 1.5442(13) . ?
C4 C5 1.5115(13) . ?
C5 C6 1.3302(15) . ?
C6 C7 1.5081(14) . ?
