#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/71/1507141.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1507141
loop_
_publ_author_name
'Mandai, Toshihiko'
'Masu, Hyuma'
'Imanari, Mamoru'
'Nishikawa, Keiko'
_publ_section_title
;
 Comparison between cycloalkyl- and n-alkyl-substituted imidazolium-based
 ionic liquids in physicochemical properties and reorientational dynamics.
;
_journal_issue                   7
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              2059
_journal_page_last               2064
_journal_paper_doi               10.1021/jp210273q
_journal_volume                  116
_journal_year                    2012
_chemical_formula_moiety         'C9 H15 N2, C7 H7 O3 S'
_chemical_formula_sum            'C16 H22 N2 O3 S'
_chemical_formula_weight         322.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.6880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2972(4)
_cell_length_b                   19.6705(9)
_cell_length_c                   9.3164(4)
_cell_measurement_reflns_used    3448
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.31
_cell_volume                     1613.96(12)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8977
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.9384
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0371
_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/[σ²(Fo²)+(0.0469P)²+0.6697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1005
_reflns_number_gt                3032
_reflns_number_total             3639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp210273q_si_001.cif
_cod_data_source_block           Cy5OTs(a110811man1)
_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1507141
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.1982(2) 0.59867(9) 0.5355(2) 0.0416(4) Uani 1 1 d .
H1A H 0.2885 0.6273 0.5527 0.062 Uiso 1 1 calc R
H1B H 0.1198 0.6241 0.5623 0.062 Uiso 1 1 calc R
H1C H 0.1596 0.5856 0.4284 0.062 Uiso 1 1 calc R
C2 C 0.37051(18) 0.50540(8) 0.66418(17) 0.0264(3) Uani 1 1 d .
H2 H 0.4548 0.5187 0.6341 0.032 Uiso 1 1 calc R
C3 C 0.14416(19) 0.50273(9) 0.69161(19) 0.0331(4) Uani 1 1 d .
H3 H 0.0427 0.5144 0.6834 0.040 Uiso 1 1 calc R
C4 C 0.22344(19) 0.44909(9) 0.76608(19) 0.0316(4) Uani 1 1 d .
H4 H 0.1885 0.4158 0.8209 0.038 Uiso 1 1 calc R
C5 C 0.49156(18) 0.40447(8) 0.81355(18) 0.0289(3) Uani 1 1 d .
H5 H 0.5782 0.4173 0.7774 0.035 Uiso 1 1 calc R
C6 C 0.5453(2) 0.40594(9) 0.9874(2) 0.0423(4) Uani 1 1 d .
H6A H 0.6224 0.4419 1.0263 0.051 Uiso 1 1 calc R
H6B H 0.4590 0.4144 1.0254 0.051 Uiso 1 1 calc R
C7 C 0.6133(2) 0.33636(10) 1.0360(2) 0.0457(5) Uani 1 1 d .
H7A H 0.5732 0.3171 1.1138 0.055 Uiso 1 1 calc R
H7B H 0.7251 0.3397 1.0795 0.055 Uiso 1 1 calc R
C8 C 0.5695(2) 0.29090(10) 0.8952(2) 0.0475(5) Uani 1 1 d .
H8A H 0.6591 0.2815 0.8629 0.057 Uiso 1 1 calc R
H8B H 0.5274 0.2472 0.9162 0.057 Uiso 1 1 calc R
C9 C 0.4499(2) 0.33050(8) 0.7729(2) 0.0385(4) Uani 1 1 d .
H9A H 0.4549 0.3196 0.6709 0.046 Uiso 1 1 calc R
H9B H 0.3465 0.3203 0.7756 0.046 Uiso 1 1 calc R
C10 C -0.0640(2) 0.26848(10) -0.2696(2) 0.0428(4) Uani 1 1 d .
H10A H -0.0229 0.2824 -0.3497 0.064 Uiso 1 1 calc R
H10B H -0.1728 0.2789 -0.3007 0.064 Uiso 1 1 calc R
H10C H -0.0491 0.2195 -0.2521 0.064 Uiso 1 1 calc R
C11 C 0.01700(19) 0.30632(8) -0.12555(18) 0.0285(3) Uani 1 1 d .
C12 C -0.04115(18) 0.36706(8) -0.08951(17) 0.0279(3) Uani 1 1 d .
H12 H -0.1326 0.3850 -0.1573 0.033 Uiso 1 1 calc R
C13 C 0.03235(18) 0.40154(8) 0.04353(17) 0.0259(3) Uani 1 1 d .
H13 H -0.0089 0.4427 0.0668 0.031 Uiso 1 1 calc R
C14 C 0.16703(16) 0.37564(7) 0.14307(16) 0.0233(3) Uani 1 1 d .
C15 C 0.22686(18) 0.31597(8) 0.10733(18) 0.0286(3) Uani 1 1 d .
H15 H 0.3195 0.2986 0.1740 0.034 Uiso 1 1 calc R
C16 C 0.15168(19) 0.28139(8) -0.02592(18) 0.0307(3) Uani 1 1 d .
H16 H 0.1931 0.2402 -0.0489 0.037 Uiso 1 1 calc R
N1 N 0.23831(16) 0.53749(7) 0.62969(15) 0.0293(3) Uani 1 1 d .
N2 N 0.36496(14) 0.45151(6) 0.74788(14) 0.0252(3) Uani 1 1 d .
O1 O 0.40311(13) 0.38655(6) 0.38320(14) 0.0367(3) Uani 1 1 d .
O2 O 0.25790(15) 0.48838(6) 0.28692(14) 0.0401(3) Uani 1 1 d .
O3 O 0.15306(14) 0.40143(7) 0.40824(13) 0.0363(3) Uani 1 1 d .
S1 S 0.25300(4) 0.416354(19) 0.32050(4) 0.02598(12) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 N2 108.36(14)
N1 C2 H2 125.8
N2 C2 H2 125.8
C4 C3 N1 106.81(15)
C4 C3 H3 126.6
N1 C3 H3 126.6
C3 C4 N2 107.20(15)
C3 C4 H4 126.4
N2 C4 H4 126.4
N2 C5 C9 113.13(13)
N2 C5 C6 112.00(13)
C9 C5 C6 104.56(14)
N2 C5 H5 109.0
C9 C5 H5 109.0
C6 C5 H5 109.0
C7 C6 C5 105.20(15)
C7 C6 H6A 110.7
C5 C6 H6A 110.7
C7 C6 H6B 110.7
C5 C6 H6B 110.7
H6A C6 H6B 108.8
C6 C7 C8 107.50(15)
C6 C7 H7A 110.2
C8 C7 H7A 110.2
C6 C7 H7B 110.2
C8 C7 H7B 110.2
H7A C7 H7B 108.5
C9 C8 C7 105.76(15)
C9 C8 H8A 110.6
C7 C8 H8A 110.6
C9 C8 H8B 110.6
C7 C8 H8B 110.6
H8A C8 H8B 108.7
C5 C9 C8 103.64(15)
C5 C9 H9A 111.0
C8 C9 H9A 111.0
C5 C9 H9B 111.0
C8 C9 H9B 111.0
H9A C9 H9B 109.0
C11 C10 H10A 109.5
C11 C10 H10B 109.5
H10A C10 H10B 109.5
C11 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C16 C11 C12 118.53(14)
C16 C11 C10 120.48(15)
C12 C11 C10 120.99(15)
C13 C12 C11 121.06(15)
C13 C12 H12 119.5
C11 C12 H12 119.5
C12 C13 C14 119.77(14)
C12 C13 H13 120.1
C14 C13 H13 120.1
C15 C14 C13 119.63(14)
C15 C14 S1 120.63(12)
C13 C14 S1 119.60(11)
C14 C15 C16 120.22(15)
C14 C15 H15 119.9
C16 C15 H15 119.9
C11 C16 C15 120.78(15)
C11 C16 H16 119.6
C15 C16 H16 119.6
C2 N1 C3 109.08(14)
C2 N1 C1 125.03(15)
C3 N1 C1 125.85(15)
C2 N2 C4 108.54(14)
C2 N2 C5 124.87(13)
C4 N2 C5 126.55(13)
O3 S1 O1 113.46(8)
O3 S1 O2 112.84(8)
O1 S1 O2 112.78(8)
O3 S1 C14 104.73(7)
O1 S1 C14 106.24(7)
O2 S1 C14 105.92(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.466(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 N1 1.326(2)
C2 N2 1.3267(19)
C2 H2 0.9500
C3 C4 1.346(2)
C3 N1 1.375(2)
C3 H3 0.9500
C4 N2 1.380(2)
C4 H4 0.9500
C5 N2 1.468(2)
C5 C9 1.522(2)
C5 C6 1.534(2)
C5 H5 1.0000
C6 C7 1.515(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.531(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.526(3)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.508(2)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C16 1.387(2)
C11 C12 1.396(2)
C12 C13 1.386(2)
C12 H12 0.9500
C13 C14 1.394(2)
C13 H13 0.9500
C14 C15 1.384(2)
C14 S1 1.7794(15)
C15 C16 1.391(2)
C15 H15 0.9500
C16 H16 0.9500
O1 S1 1.4526(12)
O2 S1 1.4548(12)
O3 S1 1.4507(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651782
2 PubChem 139039929
