Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks.
Austin, Kerrie A. B.; Elsworth, Jon D.; Banwell, Martin G.; Willis, Anthony C.; Organic & biomolecular chemistry 8 (2010) 751–754; doi:10.1039/b921600f

data_7153279
_publ_section_title
;
 Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused
 bicyclo[2.2.2]octane and related tricyclic frameworks.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              751
_journal_page_last               754
_journal_paper_doi               10.1039/b921600f
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H18 O3'
_chemical_formula_sum            'C18 H18 O3'
_chemical_formula_weight         282.34
_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
_audit_creation_date             08-06-23
_audit_creation_method           CRYSTALS_ver_12.85
_audit_update_record
;
2008-06-23 - Report on C18 H18 O3
by Anthony C. Willis
for Kerrie Austin and Martin Banwell

2008-06-23 - passes checkcif tests with minor warnings

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7159(2)
_cell_length_b                   9.7758(2)
_cell_length_c                   14.8253(4)
_cell_measurement_reflns_used    10654
_cell_measurement_temperature    200
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2.6
_cell_volume                     1408.12(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18313
_diffrn_reflns_theta_full        30.043
_diffrn_reflns_theta_max         30.043
_diffrn_reflns_theta_min         2.956
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.12
_refine_ls_abs_structure_details
;
The enantiomer has been assigned by reference to an unchanging chiral
centre in the synthetic procedure.
;
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9550
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.004411
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.00P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0810
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0810
_reflns_limit_h_max              13
_reflns_limit_h_min              0
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2075
_reflns_number_total             2326
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.42
_oxford_diffrn_Wilson_scale      0.35
_oxford_refine_ls_r_factor_ref   0.0341
_oxford_refine_ls_scale          1.885(14)
_oxford_reflns_number_all        2326
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '6231006 ban0814'
_cod_data_source_file            b921600f.txt
_cod_data_source_block           ban0814
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               7153279