Synthesis of Stereoisomers of Artemisia and Chrysanthemum Bis(acetylenic) Enol Ether Spiroacetals
Boshen Wu; George C. Feast; Amber L. Thompson; Jeremy Robertson; Journal of Organic Chemistry 77 (2012) 10623–10630; doi:10.1021/jo301810d

data_4027757
_publ_contact_author             'Jeremy Robertson'
_publ_contact_author_email       jeremy.robertson@chem.ox.ac.uk
_publ_section_title
;
 Synthesis of Stereoisomers of Artemisia and Chrysanthemum Bis(acetylenic)
 Enol Ether Spiroacetals
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10623
_journal_page_last               10630
_journal_paper_doi               10.1021/jo301810d
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C18 H20 O6'
_chemical_formula_sum            'C18 H20 O6'
_chemical_formula_weight         332.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             12-07-18
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                95.4220(10)
_cell_angle_beta                 112.7103(12)
_cell_angle_gamma                99.3154(13)
_cell_formula_units_Z            2
_cell_length_a                   8.8737(2)
_cell_length_b                   9.7374(2)
_cell_length_c                   11.2420(3)
_cell_measurement_reflns_used    3236
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1
_cell_volume                     871.01(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10446
_diffrn_reflns_theta_full        25.577
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.513
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.0003456
_refine_ls_shift/su_mean         0.0000388
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 112. 182. 108. 44.5 10.4 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1104
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1104
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3479
_reflns_number_total             3945
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.69
_oxford_diffrn_Wilson_scale      0.12
_oxford_refine_ls_r_factor_ref   0.0476
_oxford_refine_ls_scale          3.01(3)
_oxford_reflns_number_all        3941
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 005jr11
_cod_data_source_file            jo301810d_si_002_2.cif
_cod_data_source_block           Z-trans-4a
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4027757
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  43,X'S) H   (  42,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  10,X'S) H   ( 103,X'S) H   ( 102,X'S) H   ( 101,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;