Iterative stereospecific reagent-controlled homologation using a functionalized α-chloroalkyllithium: synthesis of cyclic targets related to epibatidine.
Emerson, Christopher R.; Zakharov, Lev N.; Blakemore, Paul R.; Organic letters 13 (2011) 1318–1321; doi:10.1021/ol103170y

data_1501980
_publ_section_title
;
 Iterative stereospecific reagent-controlled homologation using a
 functionalized \a-chloroalkyllithium: synthesis of cyclic targets related
 to epibatidine.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1318
_journal_page_last               1321
_journal_paper_doi               10.1021/ol103170y
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H20 Cl N O5'
_chemical_formula_sum            'C15 H20 Cl N O5'
_chemical_formula_weight         329.77
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0356(7)
_cell_length_b                   11.0921(10)
_cell_length_c                   17.5466(16)
_cell_measurement_reflns_used    9194
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.17
_cell_volume                     1564.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
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_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17516
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_correction_T_min  0.9029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0575P)^2^+0.1147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0788
_reflns_number_gt                3324
_reflns_number_total             3419
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol103170y_si_003.cif
_cod_data_source_block           pb28(RRDD17)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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)2(1)2(1)
_cod_database_code               1501980