Pro-fragrant ionic liquids with stable hemiacetal motifs: water-triggered release of fragrances
H.Q. Nimal Gunaratne; Peter Nockemann; Kenneth R. Seddon; Chem.Commun. 51 (2015) 4455–; doi:10.1039/C5cc00099H

data_7116646
_publ_section_title
;
 Pro-fragrant ionic liquids with stable hemiacetal motifs: water-triggered
 release of fragrances
;
_journal_name_full               Chem.Commun.
_journal_page_first              4455
_journal_paper_doi               10.1039/C5cc00099H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'I, C15 H18 N O2'
_chemical_formula_sum            'C15 H18 I N O2'
_chemical_formula_weight         371.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.25 svn.r3098 for OlexSys, GUI svn.r4951)
;
_audit_update_record
;
2015-01-08 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.996(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3649(2)
_cell_length_b                   15.0028(4)
_cell_length_c                   11.1821(7)
_cell_measurement_temperature    100(2)
_cell_volume                     1568.93(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17143
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    2.039
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0143
_refine_ls_R_factor_gt           0.0134
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0151P)^2^+0.7348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0337
_refine_ls_wR_factor_ref         0.0340
_reflns_number_gt                3416
_reflns_number_total             3585
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00099h2.cif
_cod_data_source_block           2011ncs0537
_cod_database_code               7116646
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C003(H00A,H00B), C007(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C005(H005), C008(H008), C010(H010), C011(H011), C012(H012), C013(H013),
 C016(H016), C017(H017), C018(H018)
2.d Idealised Me refined as rotating group:
 C009(H00E,H00F,H00G)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'