#------------------------------------------------------------------------------
#$Date: 2016-07-04 15:38:37 +0300 (Mon, 04 Jul 2016) $
#$Revision: 184171 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/20/4032020.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_4032020
loop_
_publ_author_name
'Clay, Julia M.'
'Hesek, Dusan'
'Oliver, Allen G.'
'Lee, Mijoon'
'Fisher, Jed F.'
_publ_section_title
;
 Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5705
_journal_page_last               5709
_journal_paper_doi               10.1021/acs.joc.6b00756
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_compound_source
'Julia M. Clay, SIP student in Jed Fisher lab'
_chemical_formula_sum            'C10 H14 O4'
_chemical_formula_weight         198.21
_chemical_name_common            'PNU-143663  29580-jff-20B'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             8/1998
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.968(5)
_cell_length_b                   8.073(5)
_cell_length_c                   17.744(10)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      5.18
_cell_volume                     998.1(11)
_computing_cell_refinement       Denzo
_computing_data_collection       Mar/ADSC
_computing_data_reduction        Denzo
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      158(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measurement_device_type  'Mar Imaging Plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5737
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         5.18
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.84(275)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.089
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          -0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0803P)²+0.5829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                999
_reflns_number_total             1140
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00756_si_002.cif
_cod_data_source_block           compound4
_cod_database_code               4032020
_database_code_name              JMC1
_refine_ls_restrained_s_ref      1.104
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.8495(5) 1.0537(4) 0.3190(2) 0.0289(7) Uani 1 d .
H1 H 0.8124(5) 1.1493(4) 0.2882(2) 0.035 Uiso 1 calc R
C2 C 0.9546(5) 1.0942(4) 0.3920(2) 0.0281(7) Uani 1 d .
O2H O 1.1222(3) 1.1857(3) 0.37168(12) 0.0322(6) Uani 1 d .
H2H H 1.1826(3) 1.2097(3) 0.40982(12) 0.048 Uiso 1 calc R
O3 O 1.1225(4) 0.9425(3) 0.48790(12) 0.0337(6) Uani 1 d .
C3 C 1.0183(5) 0.9346(5) 0.4327(2) 0.0290(7) Uani 1 d .
C4 C 0.9575(6) 0.7702(4) 0.3999(2) 0.0335(8) Uani 1 d .
H4A H 0.8717(6) 0.7150(4) 0.4348(2) 0.040 Uiso 1 calc R
H4B H 1.0698(6) 0.7006(4) 0.3933(2) 0.040 Uiso 1 calc R
C5 C 0.8569(5) 0.7911(5) 0.3245(2) 0.0333(8) Uani 1 d .
H5 H 0.8258(5) 0.6880(5) 0.2979(2) 0.040 Uiso 1 calc R
C6 C 0.6902(5) 0.9192(5) 0.3304(2) 0.0339(8) Uani 1 d .
C7 C 0.9691(5) 0.9203(5) 0.2781(2) 0.0338(8) Uani 1 d .
H7A H 0.9464(5) 0.9144(5) 0.2243(2) 0.041 Uiso 1 calc R
H7B H 1.1053(5) 0.9243(5) 0.2893(2) 0.041 Uiso 1 calc R
O8 O 0.8281(4) 1.1825(4) 0.51248(13) 0.0465(8) Uani 1 d .
C8 C 0.8372(5) 1.2041(5) 0.4455(2) 0.0304(8) Uani 1 d .
O8H O 0.7529(4) 1.3284(4) 0.41074(14) 0.0485(8) Uani 1 d .
H8H H 0.6921(4) 1.3835(4) 0.44138(14) 0.073 Uiso 1 calc R
C9 C 0.5662(5) 0.9206(5) 0.4002(2) 0.0425(9) Uani 1 d .
H9A H 0.6464(5) 0.9217(5) 0.4442(2) 0.064 Uiso 1 calc R
H9B H 0.4868(5) 0.8235(5) 0.4009(2) 0.064 Uiso 1 calc R
H9C H 0.4864(5) 1.0176(5) 0.4000(2) 0.064 Uiso 1 calc R
C10 C 0.5603(6) 0.9125(6) 0.2609(2) 0.0475(10) Uani 1 d .
H10A H 0.6374(6) 0.9193(6) 0.2161(2) 0.071 Uiso 1 calc R
H10B H 0.4720(6) 1.0037(6) 0.2621(2) 0.071 Uiso 1 calc R
H10C H 0.4901(6) 0.8102(6) 0.2608(2) 0.071 Uiso 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C2 C1 C7 106.9(3)
C2 C1 C6 112.3(3)
C7 C1 C6 87.7(3)
O2H C2 C1 106.8(2)
O2H C2 C8 107.0(3)
C1 C2 C8 113.2(3)
O2H C2 C3 108.4(3)
C1 C2 C3 110.9(3)
C8 C2 C3 110.2(3)
O3 C3 C4 121.5(3)
O3 C3 C2 120.2(3)
C4 C3 C2 118.2(3)
C3 C4 C5 111.9(3)
C4 C5 C7 108.1(3)
C4 C5 C6 110.9(3)
C7 C5 C6 88.0(3)
C9 C6 C10 108.9(3)
C9 C6 C5 119.1(3)
C10 C6 C5 111.2(3)
C9 C6 C1 120.4(3)
C10 C6 C1 109.9(3)
C5 C6 C1 85.6(2)
C5 C7 C1 87.0(2)
O8 C8 O8H 123.3(3)
O8 C8 C2 123.7(3)
O8H C8 C2 112.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.524(4)
C1 C7 1.542(5)
C1 C6 1.566(5)
C2 O2H 1.428(4)
C2 C8 1.535(5)
C2 C3 1.543(5)
O3 C3 1.220(4)
C3 C4 1.510(5)
C4 C5 1.520(5)
C5 C7 1.541(5)
C5 C6 1.559(5)
C6 C9 1.511(5)
C6 C10 1.531(5)
O8 C8 1.203(4)
C8 O8H 1.316(4)
