Metalated Nitriles: Chelation-Controlled Cyclizations to cis and trans Hydrindanes and Decalins
Fraser F. Fleming; Viet Anh Vu; Brian C. Shook; Moshfiqur Rahman; Omar W. Steward; Journal of Organic Chemistry 72 (2007) 1431–1436; doi:10.1021/jo062270r

data_4022737
_publ_contact_author_address
;
 Department of Chemistry and Biochemistry
 Duquesne University
 Pittsburgh, PA 15282 USA
;
_publ_contact_author_email       steward@duq.edu
_publ_contact_author_fax         ' (412) 396 5683 '
_publ_contact_author_name        'Omar W. Steward'
_publ_contact_author_phone       ' (412) 396 6338 '
_publ_section_title
;
 Metalated Nitriles: Chelation-Controlled Cyclizations to
 cis and trans Hydrindanes and Decalins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1431
_journal_page_last               1436
_journal_paper_doi               10.1021/jo062270r
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C17 H19 Cl N2 O4'
_chemical_formula_sum            'C17 H19 Cl N2 O4'
_chemical_formula_weight         350.79
_chemical_melting_point          349
_chemical_name_systematic
; 
3-(4-chlorobutyl)-2-cyanocyclopentyl 
4-nitrobenzoate  
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'Sept. 11, 2006'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.357(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.8483(10)
_cell_length_b                   5.3181(2)
_cell_length_c                   11.8833(4)
_cell_measurement_reflns_used    38662
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.85
_cell_measurement_theta_min      2.40
_cell_volume                     1725.46(11)
_computing_cell_refinement       'SMART (Bruker 1998)'
_computing_data_collection       'SMART (Bruker 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXL (Sheldrick, 1997)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.906
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  '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  0.1031
_diffrn_reflns_av_sigmaI/netI    0.0816
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38662
_diffrn_reflns_theta_full        23.85
_diffrn_reflns_theta_max         23.85
_diffrn_reflns_theta_min         1.49
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         2395
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Sheldrick 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.919
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                1236
_reflns_number_total             2395
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062270rsi20061102_024837.cif
_cod_data_source_block           vu154
_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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '349 K' was changed to '349' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022737