Symmetrical Imidazolium Chloride Based on (-)-Menthol: Synthesis, Characterization, and Theoretical Model of the Reaction.
Feder-Kubis, Joanna; Szefczyk, Borys; Kubicki, Maciej; The Journal of organic chemistry 80 (2014) 237–; doi:10.1021/jo502317m

data_4030375
_publ_contact_author
;
Maciej Kubicki   
Faculty of Chemistry 
Adam Mickiewicz University
Grunwaldzka 6              
60-780 Pozna\'n   
Poland             
;
_publ_section_title
;
 Symmetrical Imidazolium Chloride Based on (-)-Menthol: Synthesis,
 Characterization, and Theoretical Model of the Reaction.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              237
_journal_paper_doi               10.1021/jo502317m
_journal_volume                  80
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H24 N2 O'
_chemical_formula_sum            'C14 H24 N2 O'
_chemical_formula_weight         236.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.614(13)
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_cell_length_a                   6.2999(11)
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_cell_length_c                   14.823(2)
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_cell_measurement_temperature    100(1)
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_cell_measurement_theta_min      2.6310
_cell_volume                     717.60(19)
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
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_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 8.1929
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_k_min       -9
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_diffrn_reflns_number            4678
_diffrn_reflns_point_group_measured_fraction_full 0.785
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_diffrn_reflns_theta_full        25.000
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_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
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;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 573 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.5(10)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2219
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0521
_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^)+(0.0741P)^2^+0.0057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.471
_reflns_Friedel_fraction_full    0.552
_reflns_Friedel_fraction_max     0.544
_reflns_number_gt                2020
_reflns_number_total             2219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502317m_si_004.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 4030375.cif.'
_cod_original_cell_volume        717.6(2)
_cod_database_code               4030375
_shelxl_version_number           2013-4
_shelx_res_checksum              96955
_shelx_hkl_checksum              86897