#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/67/4126766.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_4126766
loop_
_publ_author_name
'Condakes, Matthew L.'
'Hung, Kevin'
'Harwood, Stephen'
'Maimone, Thomas J.'
_publ_section_title
;
 Total Syntheses of (-)-Majucin and (-)-Jiadifenoxolane A, Complex
 Majucin-Type Illicium Sesquiterpenes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b11493
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H18 O5'
_chemical_formula_weight         278.29
_chemical_name_common            MLC-VI-120
_chemical_name_systematic        maimone98
_space_group.centring_type       P
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1443(3)
_cell_length_b                   12.9075(5)
_cell_length_c                   14.2650(6)
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.34
_cell_measurement_theta_min      3.10
_cell_volume                     1315.45(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2016
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_refln_scan_rate          1
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16873
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.371
_diffrn_reflns_theta_min         4.620
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
; 
 Flack x determined using 974 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0295
_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)+(0.0363P)²+0.3339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2375
_reflns_number_total             2420
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b11493_si_002.cif
_cod_data_source_block           maimone98
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_database_code               4126766
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2016/6
_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_min   0.949
_shelx_estimated_absorpt_t_max   0.974
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.0297(3) 0.44490(16) 0.56870(14) 0.0255(4) Uani 1 1 d . .
H1 H -0.023724 0.440937 0.633397 0.031 Uiso 1 1 calc R U
C2 C -0.0587(3) 0.53913(17) 0.52152(14) 0.0290(5) Uani 1 1 d . .
H2A H -0.024149 0.542975 0.454403 0.035 Uiso 1 1 calc R U
H2B H -0.196782 0.537900 0.527222 0.035 Uiso 1 1 calc R U
C3 C 0.0256(3) 0.62892(16) 0.57677(15) 0.0270(4) Uani 1 1 d . .
H3A H -0.033761 0.635384 0.639208 0.032 Uiso 1 1 calc R U
H3B H 0.011095 0.695145 0.542522 0.032 Uiso 1 1 calc R U
C4 C 0.2321(3) 0.59899(14) 0.58566(13) 0.0216(4) Uani 1 1 d . .
C5 C 0.3478(3) 0.63183(15) 0.67402(12) 0.0215(4) Uani 1 1 d . .
C6 C 0.5015(3) 0.71053(16) 0.65430(14) 0.0260(4) Uani 1 1 d . .
H6A H 0.574954 0.688313 0.598989 0.031 Uiso 1 1 calc R U
H6B H 0.444878 0.778764 0.640148 0.031 Uiso 1 1 calc R U
C7 C 0.6899(3) 0.63318(16) 0.77634(13) 0.0249(4) Uani 1 1 d . .
C8 C 0.6060(3) 0.53302(15) 0.74762(12) 0.0230(4) Uani 1 1 d . .
C9 C 0.4430(3) 0.53160(16) 0.70255(13) 0.0224(4) Uani 1 1 d . .
C10 C 0.3322(3) 0.43993(16) 0.67070(14) 0.0264(4) Uani 1 1 d . .
H10A H 0.237263 0.420356 0.718033 0.032 Uiso 1 1 calc R U
H10B H 0.414798 0.379755 0.658799 0.032 Uiso 1 1 calc R U
C11 C 0.2383(3) 0.47702(14) 0.57928(13) 0.0208(4) Uani 1 1 d . .
C12 C 0.3603(3) 0.45777(16) 0.49286(15) 0.0282(4) Uani 1 1 d . .
H12A H 0.479736 0.424686 0.511309 0.034 Uiso 1 1 calc R U
H12B H 0.294802 0.411522 0.448252 0.034 Uiso 1 1 calc R U
C13 C 0.3968(3) 0.56146(16) 0.44830(13) 0.0232(4) Uani 1 1 d . .
C14 C -0.0064(3) 0.34033(18) 0.52242(17) 0.0355(5) Uani 1 1 d . .
H14A H -0.140712 0.324988 0.524190 0.053 Uiso 1 1 calc R U
H14B H 0.062238 0.286227 0.556197 0.053 Uiso 1 1 calc R U
H14C H 0.036026 0.342552 0.457121 0.053 Uiso 1 1 calc R U
C15 C 0.2215(3) 0.67221(18) 0.75342(14) 0.0298(5) Uani 1 1 d . .
H15A H 0.136068 0.617070 0.773422 0.045 Uiso 1 1 calc R U
H15B H 0.148757 0.731548 0.730811 0.045 Uiso 1 1 calc R U
H15C H 0.299185 0.693742 0.806572 0.045 Uiso 1 1 calc R U
O1 O 0.6247(2) 0.71964(11) 0.73557(10) 0.0295(3) Uani 1 1 d . .
O2 O 0.3249(2) 0.63748(10) 0.50132(9) 0.0255(3) Uani 1 1 d . .
O3 O 0.8099(2) 0.63852(12) 0.83571(10) 0.0327(4) Uani 1 1 d . .
O4 O 0.6972(2) 0.44598(11) 0.77517(10) 0.0278(3) Uani 1 1 d . .
H4 H 0.792901 0.462411 0.805971 0.042 Uiso 1 1 calc R U
O5 O 0.4787(2) 0.58096(12) 0.37663(10) 0.0317(4) 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 0.0181 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
C14 C1 C2 116.39(17)
C14 C1 C11 116.13(17)
C2 C1 C11 103.11(16)
C14 C1 H1 106.8
C2 C1 H1 106.8
C11 C1 H1 106.8
C3 C2 C1 102.37(16)
C3 C2 H2A 111.3
C1 C2 H2A 111.3
C3 C2 H2B 111.3
C1 C2 H2B 111.3
H2A C2 H2B 109.2
C2 C3 C4 103.39(16)
C2 C3 H3A 111.1
C4 C3 H3A 111.1
C2 C3 H3B 111.1
C4 C3 H3B 111.1
H3A C3 H3B 109.0
O2 C4 C3 106.47(16)
O2 C4 C5 109.36(15)
C3 C4 C5 120.47(17)
O2 C4 C11 106.21(15)
C3 C4 C11 105.92(16)
C5 C4 C11 107.56(16)
C9 C5 C6 107.15(16)
C9 C5 C15 110.75(15)
C6 C5 C15 109.45(16)
C9 C5 C4 102.82(15)
C6 C5 C4 114.37(15)
C15 C5 C4 112.01(16)
O1 C6 C5 109.99(15)
O1 C6 H6A 109.7
C5 C6 H6A 109.7
O1 C6 H6B 109.7
C5 C6 H6B 109.7
H6A C6 H6B 108.2
O3 C7 O1 120.21(19)
O3 C7 C8 122.1(2)
O1 C7 C8 117.72(17)
C9 C8 O4 123.29(18)
C9 C8 C7 119.96(18)
O4 C8 C7 116.61(17)
C8 C9 C10 128.43(18)
C8 C9 C5 120.70(18)
C10 C9 C5 110.85(16)
C9 C10 C11 103.99(15)
C9 C10 H10A 111.0
C11 C10 H10A 111.0
C9 C10 H10B 111.0
C11 C10 H10B 111.0
H10A C10 H10B 109.0
C12 C11 C10 112.52(16)
C12 C11 C1 115.12(16)
C10 C11 C1 114.61(16)
C12 C11 C4 102.98(15)
C10 C11 C4 105.85(16)
C1 C11 C4 104.17(16)
C13 C12 C11 107.14(16)
C13 C12 H12A 110.3
C11 C12 H12A 110.3
C13 C12 H12B 110.3
C11 C12 H12B 110.3
H12A C12 H12B 108.5
O5 C13 O2 120.78(19)
O5 C13 C12 128.95(19)
O2 C13 C12 110.26(16)
C1 C14 H14A 109.5
C1 C14 H14B 109.5
H14A C14 H14B 109.5
C1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C5 C15 H15A 109.5
C5 C15 H15B 109.5
H15A C15 H15B 109.5
C5 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C7 O1 C6 119.10(15)
C13 O2 C4 112.92(15)
C8 O4 H4 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C14 1.525(3)
C1 C2 1.527(3)
C1 C11 1.555(3)
C1 H1 1.0000
C2 C3 1.525(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.530(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 O2 1.461(2)
C4 C5 1.566(3)
C4 C11 1.578(3)
C5 C9 1.517(3)
C5 C6 1.522(3)
C5 C15 1.539(3)
C6 O1 1.460(2)
C6 H6A 0.9900
C6 H6B 0.9900
C7 O3 1.207(3)
C7 O1 1.342(3)
C7 C8 1.483(3)
C8 C9 1.330(3)
C8 O4 1.357(2)
C9 C10 1.494(3)
C10 C11 1.543(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.530(3)
C12 C13 1.504(3)
C12 H12A 0.9900
C12 H12B 0.9900
C13 O5 1.205(2)
C13 O2 1.341(2)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
O4 H4 0.8400
