Synthesis and applications of novel bis(ammonium) chiral ionic liquids derived from isomannide.
Kumar, Vineet; Olsen, Carl E.; Schäffer, Susan J C; Parmar, Virinder S.; Malhotra, Sanjay V.; Organic letters 9 (2007) 3905–3908; doi:10.1021/ol071390y

data_1505500
_publ_contact_author
; 
Susan J. Cline Sch\"affer 
The Technical University of Denmark 
The Department of Chemistry 
Building 207 
DK-2800 Lyngby 
Denmark 
 
;
_publ_section_title
;
 Synthesis and applications of novel bis(ammonium) chiral ionic liquids
 derived from isomannide.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              3905
_journal_page_last               3908
_journal_paper_doi               10.1021/ol071390y
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H34 N2 O2, H2 O, I2'
_chemical_formula_sum            'C24 H36 I2 N2 O3'
_chemical_formula_weight         654.35
_chemical_name_systematic
; 
(1R,4S,5R,8S)-4,8-bis(dimethylbenzylammonium)-2,6-dioxabicyclo [3.3.0] 
octane iodide--water (1/1) 
 
 
;
_space_group_IT_number           19
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_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
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_audit_creation_method           SHELXL-97
_audit_update_record
; 
ss 25/03-2007 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6096(4)
_cell_length_b                   11.4063(5)
_cell_length_c                   24.2743(11)
_cell_measurement_reflns_used    8525
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.5
_cell_volume                     2660.7(2)
_computing_cell_refinement       'SAINT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.22 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2001)'
_computing_publication_material  'XCIF (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
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_diffrn_radiation_wavelength_id  s17aas
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_diffrn_reflns_limit_l_min       -32
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_diffrn_standards_decay_%        2.3
_diffrn_standards_interval_time  812
_diffrn_standards_number         445
_exptl_absorpt_coefficient_mu    2.390
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_exptl_absorpt_correction_T_min  0.6229
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP (Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platey
_exptl_crystal_F_000             1296
_exptl_crystal_id                s17aas
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; 
The data crystal was mounted using oil on a thin glass fiber 
with the 0 -1 0 scattering planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.851
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack (1983),  2791 Friedels'
_refine_ls_abs_structure_Flack   -0.017(13)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         6398
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0206
_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^)+(0.0248P)^2^+1.1907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0481
_refine_ls_wR_factor_ref         0.0488
_reflns_number_gt                6311
_reflns_number_total             6398
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol071390y-file001.cif
_cod_data_source_block           s17aas
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               1505500