The first asymmetric total synthesis of (+)-coriandrone A and B.
Wang, Wenjing; Xue, Jijun; Tian, Tian; Jiao, Yingdong; Li, Ying; Organic & biomolecular chemistry 11 (2013) 6686–6690; doi:10.1039/c3ob41497c

data_7153124
_publ_section_title
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 The first asymmetric total synthesis of (+)-coriandrone A and B.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6686
_journal_page_last               6690
_journal_paper_doi               10.1039/c3ob41497c
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H20 O5'
_chemical_formula_sum            'C9 H0 N8 O4'
_chemical_formula_weight         284.17
_chemical_name_systematic
;
 ? 
;
_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_date             2013-03-28
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7505(5)
_cell_length_b                   10.8915(6)
_cell_length_c                   15.6217(7)
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7210
_cell_measurement_theta_min      3.9540
_cell_volume                     1488.84(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9955
_diffrn_measured_fraction_theta_max 0.7913
_diffrn_measurement_details
;
  1 omega  -81.00  -40.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -57.0000 -120.0000 27

  2 omega  -45.00   69.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -19.0000    0.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0533609000
_diffrn_orient_matrix_UB_12      0.0352569000
_diffrn_orient_matrix_UB_13      -0.0237558000
_diffrn_orient_matrix_UB_21      -0.0251410000
_diffrn_orient_matrix_UB_22      -0.0539056000
_diffrn_orient_matrix_UB_23      -0.0211861000
_diffrn_orient_matrix_UB_31      -0.0555773000
_diffrn_orient_matrix_UB_32      -0.0094731000
_diffrn_orient_matrix_UB_33      0.0324083000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3946
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0407P)^2^+0.2195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                2239
_reflns_number_total             2759
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41497c.txt
_cod_data_source_block           exp_848
_cod_original_cell_volume        1488.85(14)
_cod_database_code               7153124
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H3 of C3, {H4A,H4B} of C4, H6 of C6, {H10A,H10B} of C10, H11 of C11
 At 1.5 times of:
  H4 of O4, {H16A,H16B,H16C} of C16, {H15A,H15B,H15C} of C15, {H14A,H14B,
  H14C} of C14, {H13A,H13B,H13C} of C13
2.a Ternary CH refined with riding coordinates:
 C3(H3), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
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