Three-Carbon Homologation of Diorganozincs with Lithiated Acetylenic Epoxides
Aurélien Denichoux; Laurent Debien; Mathieu Cyklinsky; Malika Kaci; Fabrice Chemla; Franck Ferreira; Alejandro Pérez-Luna; Journal of Organic Chemistry 78 (2013) 134–145; doi:10.1021/jo302128n

data_4027836
_publ_contact_author_address
; 
Institut Parisien de Chimie Moleculaire (IPCM), UMR 7201,
Universite Pierre et Marie Curie, 4 place Jussieu,
75252 Paris cedex 5, France
;
_publ_contact_author_email       franck.ferreira@upmc.fr
_publ_contact_author_fax         '+33 1 44 27 75 67'
_publ_contact_author_name        'Franck Ferreira'
_publ_contact_author_phone       '+33 1 44 27 55 71 '
_publ_section_title
;
 Three-Carbon Homologation of Diorganozincs with Lithiated Acetylenic
 Epoxides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              134
_journal_page_last               145
_journal_paper_doi               10.1021/jo302128n
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C21 H36 O2'
_chemical_formula_sum            'C21 H36 O2'
_chemical_formula_weight         320.52
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             12-09-27
_audit_creation_method           CRYSTALS_ver_14.23
_cell_angle_alpha                90
_cell_angle_beta                 105.495(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7491(15)
_cell_length_b                   21.6842(17)
_cell_length_c                   9.9916(14)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    250
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     2035.5(5)
_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    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      250
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_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  0.048
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19046
_diffrn_reflns_theta_full        25.205
_diffrn_reflns_theta_max         30.006
_diffrn_reflns_theta_min         2.314
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.046
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0129
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.0004027
_refine_ls_structure_factor_coef F
_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: 
 0.709 0.126 0.272 -0.196 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0921
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0571
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3159
_reflns_number_total             5879
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.32
_oxford_diffrn_Wilson_scale      3.58
_oxford_refine_ls_r_factor_ref   0.0511
_oxford_refine_ls_scale          0.6277(13)
_oxford_reflns_number_all        5876
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_oxford_structure_analysis_title '6160941 Compound X'
_cod_data_source_file            jo302128n_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'refu' changed to 'refU'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4027836
_iucr_refine_instruction_details_constraints
;
FULL  C(1,X'S,U'S) UNTIL O(23) H(11,U[ISO]) UNTIL LAST 
EQUIV H(11,U[ISO]) UNTIL LAST 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
END                                                                             
;