Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles.
Lang, Simon B.; Locascio, Theresa M.; Tunge, Jon A.; Organic letters 16 (2014) 4308–4311; doi:10.1021/ol502023d

data_1517501
_publ_section_title
;
 Activation of alcohols with carbon dioxide: intermolecular allylation of
 weakly acidic pronucleophiles.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4308
_journal_page_last               4311
_journal_paper_doi               10.1021/ol502023d
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C19 H24 Cl N O'
_chemical_formula_weight         317.84
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'C -1'
_symmetry_space_group_name_Hall  '-P 1 (1/2*x+1/2*y,1/2*x-1/2*y,-z)'
_symmetry_space_group_name_H-M   'C -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90.4219(6)
_cell_angle_beta                 104.5435(4)
_cell_angle_gamma                89.7970(4)
_cell_formula_units_Z            16
_cell_length_a                   26.96214(19)
_cell_length_b                   12.68483(10)
_cell_length_c                   21.88641(18)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.67
_cell_measurement_theta_min      3.39
_cell_volume                     7245.32(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32353
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         70.051
_diffrn_reflns_theta_min         2.085
_exptl_absorpt_coefficient_mu    1.864
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       Paralllelpiped
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     867
_refine_ls_number_reflns         11861
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0776
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0988P)^2^+22.0591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2045
_refine_ls_wR_factor_ref         0.2130
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10457
_reflns_number_total             11861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502023d_si_002.cif
_cod_data_source_block           q19eC-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group_crystal_system' value 'Triclinic' changed to
'triclinic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        7245.31(10)
_cod_database_code               1517501
_shelx_estimated_absorpt_t_min   0.653
_shelx_estimated_absorpt_t_max   0.843
_shelxl_version_number           2013-4
_shelx_res_checksum              39384
_shelx_hkl_checksum              83181