Conformational and Configurational Analysis in the Study and Synthesis of Chlorinated Natural Products
Christian Nilewski; Roger W. Geisser; Marc-Olivier Ebert; Erick M. Carreira; Journal of the American Chemical Society 131 (2009) 15866–15876; doi:10.1021/ja906461h

data_4105251
_publ_contact_author_address
;ETH Z\"urich
Laboratory of Organic Chemistry
HCI H330
Wolfgang-Pauli-Strasse 10
8093 Z\"urich
;
_publ_contact_author_email       cnilewski@org.chem.ethz.ch
_publ_contact_author_fax         '+41 44 632 13 28'
_publ_contact_author_name        'Christian Nilewski'
_publ_contact_author_phone       '+41 44 632 29 43'
_publ_section_title
;
 Conformational and Configurational Analysis in the Study and Synthesis of
 Chlorinated Natural Products
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15866
_journal_page_last               15876
_journal_paper_doi               10.1021/ja906461h
_journal_volume                  131
_journal_year                    2009
_chemical_compound_source        'LOC ETH Zurich'
_chemical_formula_moiety         'C6 H11 Cl3 O2 '
_chemical_formula_sum            'C6 H11 Cl3 O2'
_chemical_formula_weight         221.511
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 111.962(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.6489(6)
_cell_length_b                   5.0979(2)
_cell_length_c                   20.4002(6)
_cell_measurement_reflns_used    56488
_cell_measurement_temperature    223
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.425
_cell_volume                     1895.16(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97(Altomare et al., J. Appl. Cryst.,1999)'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.03682
_diffrn_orient_matrix_UB_12      0.03940
_diffrn_orient_matrix_UB_13      0.01016
_diffrn_orient_matrix_UB_21      -0.07290
_diffrn_orient_matrix_UB_22      0.02148
_diffrn_orient_matrix_UB_23      0.18084
_diffrn_orient_matrix_UB_31      0.04471
_diffrn_orient_matrix_UB_32      -0.01951
_diffrn_orient_matrix_UB_33      0.02034
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.081
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11124
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       needle
_exptl_crystal_F_000             912.0
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .07
_exptl_crystal_size_min          .03
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1751
_reflns_number_gt                2601
_reflns_number_total             3315
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja906461h_si_007.cif
_cod_data_source_block           global
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_original_formula_sum        'C6 H11 Cl3 O2 '
_cod_database_code               4105251