Synthesis and properties of chiral imidazolium ionic liquids with a (1R,2S,5R)-(?)-menthoxymethyl substituent
Juliusz Pernak; Joanna Feder-Kubis; Anna Cieniecka-Rosłonkiewicz; Cedric Fischmeister; Scott T. Griffin; Robin D. Rogers; New Journal of Chemistry 31 (2007) 879–; doi:10.1039/b616215k

data_7052131
_publ_section_title
;
 Synthesis and properties of chiral imidazolium ionic liquids with a
 (1R,2S,5R)-(?)-menthoxymethyl substituent
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              879
_journal_paper_doi               10.1039/b616215k
_journal_volume                  31
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C16H29N2O, 0.5 H2O, Cl'
_chemical_formula_sum            'C16 H30 Cl N2 O1.5'
_chemical_formula_weight         309.87
_chemical_melting_point          144
_chemical_name_common
;
?
;
_chemical_name_systematic
; 
1-[(1R,2S,5R)--(--)--menthoxymethyl]-3-ethylimidazolium chloride hemihydrate 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.636(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0143(14)
_cell_length_b                   8.0671(8)
_cell_length_c                   17.9287(18)
_cell_measurement_reflns_used    3386
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.53
_cell_measurement_theta_min      2.78
_cell_volume                     1829.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.946
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11927
_diffrn_reflns_theta_full        25.30
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.7468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick 2004, SADABS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2421 Friedel pairs'
_refine_ls_abs_structure_Flack   0.22(7)
_refine_ls_extinction_coef       0.0030(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         7007
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0569
_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^)+(0.0963P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1668
_reflns_number_gt                4228
_reflns_number_total             7007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b616215k.txt
_cod_data_source_block           1b
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_original_formula_sum        'C16 H30 Cl N2 O1.50'
_cod_database_code               7052131