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_4027756
_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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_audit_creation_date             11-04-19
_audit_creation_method           CRYSTALS_ver_14.20
_cell_angle_alpha                90
_cell_angle_beta                 100.401(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3035(2)
_cell_length_b                   9.3322(3)
_cell_length_c                   19.7057(6)
_cell_measurement_reflns_used    8161
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      5
_cell_volume                     1682.78(8)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17364
_diffrn_reflns_theta_full        76.421
_diffrn_reflns_theta_max         76.421
_diffrn_reflns_theta_min         4.563
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0112
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.0006477
_refine_ls_shift/su_mean         0.0000882
_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: 
 0.215E+04 0.365E+04 0.227E+04 956. 218. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1178
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1175
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                3212
_reflns_number_total             3518
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.64
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0424
_oxford_refine_ls_scale          6.03(13)
_oxford_reflns_number_all        3518
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 6346
_cod_data_source_file            jo301810d_si_002_1.cif
_cod_data_source_block           Z-trans-4s
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4027756
_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   ( 102,X'S) H   ( 101,X'S) H   ( 103,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  19,X'S) H   ( 192,X'S) H   ( 191,X'S) H   ( 193,X'S) 
RIDE C   (  21,X'S) H   ( 212,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 222,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,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                                                                             
;