Asymmetric induction in 8π electrocyclizations. Design of a removable chiral auxiliary.
Kim, Keunsoo; Lauher, Joseph W.; Parker, Kathlyn A.; Organic letters 14 (2012) 138–141; doi:10.1021/ol202932x

data_1503501
_publ_section_title
;
 Asymmetric induction in 8\p electrocyclizations. Design of a removable
 chiral auxiliary.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              138
_journal_page_last               141
_journal_paper_doi               10.1021/ol202932x
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C26 H28 N2 O4'
_chemical_formula_sum            'C26 H28 N2 O4'
_chemical_formula_weight         432.50
_chemical_name_common            'bicyclo[4.2.0]octa-2,4-diene derivative'
_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
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CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
;
_cell_angle_alpha                90.00
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_cell_length_b                   11.7795(7)
_cell_length_c                   29.5906(17)
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_cell_measurement_temperature    293(2)
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_cell_measurement_theta_min      3.2148
_cell_volume                     2438.3(2)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
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_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
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_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
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_diffrn_ambient_temperature      292
_diffrn_detector_area_resol_mean 10.4962
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
; 
  1 omega   -3.00   99.00   1.0000   20.0000 
omega____ theta____ kappa____ phi______ frames 
    -       20.0511   77.0000 -150.0000 102 
  
  2 omega    1.00   48.00   1.0000   20.0000 
omega____ theta____ kappa____ phi______ frames 
    -       20.0511   37.0000   30.0000 47 
  
  3 omega  -56.00   46.00   1.0000   20.0000 
omega____ theta____ kappa____ phi______ frames 
    -       20.0511  -37.0000 -180.0000 102 
  
  4 omega   -6.00   96.00   1.0000   20.0000 
omega____ theta____ kappa____ phi______ frames 
    -       20.0511   37.0000  150.0000 102 
  
  5 omega -110.00  -61.00   1.0000   20.0000 
omega____ theta____ kappa____ phi______ frames 
    -      -20.8323  179.0000 -150.0000 49 
  
  6 omega -110.00  -53.00   1.0000   20.0000 
omega____ theta____ kappa____ phi______ frames 
    -      -20.8323  179.0000  -60.0000 57 
  
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0017485000
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_diffrn_orient_matrix_UB_13      0.0094378000
_diffrn_orient_matrix_UB_21      -0.0047260000
_diffrn_orient_matrix_UB_22      0.0236174000
_diffrn_orient_matrix_UB_23      0.0220116000
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_diffrn_orient_matrix_UB_32      -0.0020768000
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0709
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_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            24589
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          .8
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.090
_refine_diff_density_min         -0.092
_refine_diff_density_rms         0.021
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.074
_refine_ls_shift/su_mean         0.045
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0317P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_total             4976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202932x_si_002.cif
_cod_data_source_block           bicyclo_octadiene_derivative
_cod_depositor_comments
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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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     P2ac2ab
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1503501
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_theta     30.44
_reflns_odcompleteness_iscentric 1
_chemical_oxdiff_formula         C26H28N2O4