Cycloaddition of cyclohexa-2,4-dienones with electron deficient 2?? partners: a novel and stereoselective route to functionalised bicyclo[2.2.2]octenones
Singh, Vishwakarma; Pal, Shantanu; Mobin, Shaikh M.; Chemical Communications  (2002) 2050–; doi:10.1039/b205475m

data_7114048
_publ_section_title
;
 Cycloaddition of cyclohexa-2,4-dienones with electron deficient 2??
 partners: a novel and stereoselective route to functionalised
 bicyclo[2.2.2]octenones
;
_journal_issue                   18
_journal_name_full               'Chemical Communications'
_journal_page_first              2050
_journal_paper_doi               10.1039/b205475m
_journal_year                    2002
_chemical_formula_moiety
;1,7-dimethyl-5-hydroxy-5-chloromethyl-    
2-carboethoxy bicyclo[2.2.2]oct-7-ene-6-one
;
_chemical_formula_sum            'C14 H19 Cl O4'
_chemical_formula_weight         286.74
_chemical_name_common
;1,7-dimethyl-5-hydroxy-5-chloromethyl-    
2-carboethoxy bicyclo[2.2.2]oct-7-ene-6-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_formula_units_Z            8
_cell_length_a                   10.3270(12)
_cell_length_b                   14.2240(14)
_cell_length_c                   20.1930(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11.8400
_cell_measurement_theta_min      5.7100
_cell_volume                     2966.2(5)
_computing_cell_refinement       'Argus (Nonius, MACH3 software)'
_computing_data_collection       'Argus (Nonius, MACH3 software)'
_computing_data_reduction        'Maxus (Nonius software)'
_computing_molecular_graphics    Ortep
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.697
_diffrn_measured_fraction_theta_max 0.697
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength     0.70930
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2046
_diffrn_reflns_theta_full        24.91
_diffrn_reflns_theta_max         24.91
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        <3%
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
psi-scan (North, Philips & Mathews, 1968)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          '0.40 mm'
_exptl_crystal_size_mid          '0.40 mm'
_exptl_crystal_size_min          '0.35 mm'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0587P)^2^+1.3839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                1646
_reflns_number_total             2046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b205475m.txt
_cod_data_source_block           C14_H19_Cl1_O4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+1.3839P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+1.3839P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               7114048