Catalytic asymmetric synthesis of optically active allenes from terminal alkynes.
Ye, Juntao; Li, Suhua; Chen, Bo; Fan, Wu; Kuang, Jinqiang; Liu, Jinxian; Liu, Yu; Miao, Bukeyan; Wan, Baoqiang; Wang, Yuli; Xie, Xi; Yu, Qiong; Yuan, Weiming; Ma, Shengming; Organic letters 14 (2012) 1346–1349; doi:10.1021/ol300296k

data_1507178
_publ_section_title
;
 Catalytic asymmetric synthesis of optically active allenes from terminal
 alkynes.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1346
_journal_page_last               1349
_journal_paper_doi               10.1021/ol300296k
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H20 O'
_chemical_formula_weight         228.32
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.5840(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.7903(3)
_cell_length_b                   4.71280(10)
_cell_length_c                   12.0475(3)
_cell_measurement_temperature    133(2)
_cell_volume                     668.11(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9051
_diffrn_reflns_theta_full        66.26
_diffrn_reflns_theta_max         66.26
_diffrn_reflns_theta_min         3.68
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  0.9253
_exptl_absorpt_correction_T_min  0.8798
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2212
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.0826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0677
_reflns_number_gt                2202
_reflns_number_total             2212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300296k_si_002.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1507178