Asymmetric Synthesis of Bicyclo[4.3.1]decadienes and Bicyclo[3.3.2]decadienes via [6 + 3] Trimethylenemethane Cycloaddition with Tropones
Barry M. Trost; Patrick J. McDougall; Olaf Hartmann; Peter T. Wathen; Journal of the American Chemical Society 130 (2008) 14960–14961; doi:10.1021/ja806979b

data_4108652
_publ_contact_author_address     'Dept. of Chemistry, Stanford Univeristy'
_publ_contact_author_email       olafh@stanford.edu
_publ_contact_author_name        'Olaf Hartmann'
_publ_contact_author_phone       '650 723 8409'
_publ_section_title
;
 Asymmetric Synthesis of Bicyclo[4.3.1]decadienes and
 Bicyclo[3.3.2]decadienes via [6 + 3] Trimethylenemethane Cycloaddition
 with Tropones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14960
_journal_page_last               14961
_journal_paper_doi               10.1021/ja806979b
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H10 Cl N O'
_chemical_formula_sum            'C12 H10 Cl N O'
_chemical_formula_weight         219.66
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9537(14)
_cell_length_b                   9.9845(17)
_cell_length_c                   12.839(2)
_cell_measurement_reflns_used    6469
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.59
_cell_volume                     1019.6(3)
_computing_cell_refinement       'Bruker SAINT v7.34'
_computing_data_collection       'Bruker APEX-II v2.1-4'
_computing_data_reduction        'Bruker SAINT v7.34'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       \w/2\q-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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11518
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  0.9503
_exptl_absorpt_correction_T_min  0.9191
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Sheldrick, 2007'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.2019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0643
_reflns_number_gt                2437
_reflns_number_total             2528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806979b_si_003.cif
_cod_data_source_block           oh163
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'orthorhmobic' was replaced with
'orthorhombic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
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_cod_database_code               4108652