Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.
Hung, Kevin; Condakes, Matthew L.; Novaes, Luiz F. T.; Harwood, Stephen J.; Morikawa, Takahiro; Yang, Zhi; Maimone, Thomas J.; Journal of the American Chemical Society 141 (2019) 3083–3099; doi:10.1021/jacs.8b12247

data_4128470
_publ_section_title
;
 Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to
 the Illicium Sesquiterpenes.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3083
_journal_page_last               3099
_journal_paper_doi               10.1021/jacs.8b12247
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H22 O4'
_chemical_formula_sum            'C15 H22 O4'
_chemical_formula_weight         266.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.093(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8174(5)
_cell_length_b                   13.7159(5)
_cell_length_c                   16.1653(6)
_cell_measurement_temperature    100(2)
_cell_volume                     2768.02(18)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38632
_diffrn_reflns_theta_full        70.79
_diffrn_reflns_theta_max         70.79
_diffrn_reflns_theta_min         2.81
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.745
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(12)
_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     705
_refine_ls_number_reflns         10524
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.6774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                9237
_reflns_number_total             10524
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8b12247_si_006.cif
_cod_data_source_block           cu_kh3216_0m
_cod_database_code               4128470
_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:
 C00N(H00N), C00X(H00X), C01G(H9AA), C01I(H5AA)
2.b Secondary CH2 refined with riding coordinates:
 C010(H01A,H01B), C011(H01C,H01D), C018(H01H,H01I), C019(H3AA,H), C01B(H01X,
 H01Y), C01H(H0BA,HC), C01K(H1BA,HF), C01N(H01,HI), C01O(H01P,H01Q), C01T(H7AA,
 HP), C01V(H1AA,HS), C01W(H5BA,HT), C01Y(H2AA,HW), C021(H02D,H02E), C022(H02F,
 H02G), C023(H02K,H02L)
2.c Idealised Me refined as rotating group:
 C015(H01E,H01F,H01G), C017(H01U,H01V,H01W), C01A(H01J,H01K,H01L), C01C(H4AA,
 HA,HB), C01D(H01M,H01N,H01O), C01J(H6AA,HD,HE), C01L(H01Z,HG,HH), C01P(H2BA,HJ,
 HK), C01Q(H3BA,HL,HM), C01R(H4BA,HN,HO), C01S(H01R,H01S,H01T), C01U(H0AA,HQ,
 HR), C01X(H6BA,HU,HV), C01Z(H8AA,HX,HY), C020(H02A,H02B,H02C), C024(H02H,H02I,
 H02J)
2.d Idealised tetrahedral OH refined as rotating group:
 O006(H006), O007(H007), O009(H009), O00A(H00A)
;
_olex2_submission_special_instructions 'No special instructions were received'