#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/33/7203399.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_7203399
loop_
_publ_author_name
'Pernak, Juliusz'
'Smiglak, Marcin'
'Griffin, Scott T.'
'Hough, Whitney L.'
'Wilson, Timothy B.'
'Pernak, Anna'
'Zabielska-Matejuk, Jadwiga'
'Fojutowski, Andrzej'
'Kita, Kazimierz'
'Rogers, Robin D.'
_publ_section_title
;
 Long alkyl chain quaternary ammonium-based ionic liquids and potential
 applications
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              798
_journal_paper_doi               10.1039/b604353d
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C27 H42 N2 O5'
_chemical_formula_weight         474.63
_chemical_melting_point          94
_chemical_name_common            'benzethonium nitrate'
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.753(8)
_cell_angle_beta                 102.116(7)
_cell_angle_gamma                106.858(7)
_cell_formula_units_Z            2
_cell_length_a                   7.936(3)
_cell_length_b                   10.048(4)
_cell_length_c                   17.864(7)
_cell_measurement_reflns_used    1862
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.19
_cell_measurement_theta_min      2.33
_cell_volume                     1326.5(9)
_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 0.977
_diffrn_measured_fraction_theta_max 0.963
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1119
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5237
_diffrn_reflns_theta_full        25.30
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       0.25(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1503
_refine_ls_R_factor_gt           0.1123
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1870P)²+2.0752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3193
_refine_ls_wR_factor_ref         0.3388
_reflns_number_gt                3333
_reflns_number_total             5238
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b604353d.txt
_cod_data_source_block           s1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Sphere' changed to
'sphere' 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_cell_volume        1326.5(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7203399
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9291(5) 0.6648(4) 0.0322(2) 0.0310(9) Uani 1 1 d . . .
O2 O 0.5904(5) 0.5996(4) 0.0925(2) 0.0328(10) Uani 1 1 d . . .
O3 O 0.4429(6) 0.0623(5) 0.0871(3) 0.0472(12) Uani 1 1 d . . .
O4 O 0.1829(6) 0.0440(5) 0.1115(3) 0.0495(12) Uani 1 1 d . . .
O5 O 0.4222(7) 0.1869(6) 0.1833(3) 0.0634(15) Uani 1 1 d . . .
N1 N 1.0792(6) 0.7137(4) -0.1205(2) 0.0240(10) Uani 1 1 d . . .
N2 N 0.3494(6) 0.0976(4) 0.1269(3) 0.0295(11) Uani 1 1 d . . .
C1 C 1.1361(7) 0.8053(5) -0.0439(3) 0.0269(12) Uani 1 1 d . . .
H1A H 1.2650 0.8604 -0.0364 0.032 Uiso 1 1 calc R . .
H1B H 1.0651 0.8722 -0.0476 0.032 Uiso 1 1 calc R . .
C2 C 1.1129(8) 0.7282(6) 0.0273(3) 0.0320(13) Uani 1 1 d . . .
H2A H 1.1732 0.6544 0.0283 0.038 Uiso 1 1 calc R . .
H2B H 1.1760 0.7949 0.0735 0.038 Uiso 1 1 calc R . .
C3 C 0.8417(7) 0.7613(6) 0.0504(3) 0.0291(12) Uani 1 1 d . . .
H3A H 0.8668 0.8414 0.0191 0.035 Uiso 1 1 calc R . .
H3B H 0.8869 0.7973 0.1054 0.035 Uiso 1 1 calc R . .
C4 C 0.6402(8) 0.6873(6) 0.0336(3) 0.0322(13) Uani 1 1 d . . .
H4A H 0.573(7) 0.754(5) 0.031(3) 0.010(11) Uiso 1 1 d . . .
H4B H 0.599(7) 0.613(5) -0.016(3) 0.015(12) Uiso 1 1 d . . .
C5 C 0.5715(7) 0.6610(5) 0.1591(3) 0.0271(12) Uani 1 1 d . . .
C6 C 0.5498(7) 0.5757(6) 0.2179(3) 0.0309(13) Uani 1 1 d . . .
H6A H 0.5511 0.4819 0.2112 0.037 Uiso 1 1 calc R . .
C7 C 0.5258(7) 0.6275(6) 0.2872(3) 0.0326(13) Uani 1 1 d . . .
H7A H 0.5122 0.5679 0.3273 0.039 Uiso 1 1 calc R . .
C8 C 0.5211(7) 0.7636(6) 0.2993(3) 0.0267(12) Uani 1 1 d . . .
C9 C 0.5437(7) 0.8481(6) 0.2385(3) 0.0318(13) Uani 1 1 d . . .
H9A H 0.5425 0.9420 0.2450 0.038 Uiso 1 1 calc R . .
C10 C 0.5679(7) 0.7983(5) 0.1690(3) 0.0284(12) Uani 1 1 d . . .
H10A H 0.5818 0.8573 0.1287 0.034 Uiso 1 1 calc R . .
C11 C 0.4988(8) 0.8272(6) 0.3745(3) 0.0347(13) Uani 1 1 d . . .
C12 C 0.4731(10) 0.7182(8) 0.4335(4) 0.0470(17) Uani 1 1 d . . .
H12A H 0.5735 0.6780 0.4413 0.070 Uiso 1 1 calc R . .
H12B H 0.3588 0.6439 0.4141 0.070 Uiso 1 1 calc R . .
H12C H 0.4709 0.7635 0.4824 0.070 Uiso 1 1 calc R . .
C13 C 0.6738(10) 0.9459(8) 0.4099(4) 0.056(2) Uani 1 1 d . . .
H13A H 0.7763 0.9081 0.4202 0.083 Uiso 1 1 calc R . .
H13B H 0.6623 0.9876 0.4582 0.083 Uiso 1 1 calc R . .
H13C H 0.6940 1.0175 0.3740 0.083 Uiso 1 1 calc R . .
C14 C 0.3439(8) 0.8934(6) 0.3600(3) 0.0326(13) Uani 1 1 d . . .
H14A H 0.3689 0.9601 0.3211 0.039 Uiso 1 1 calc R . .
H14B H 0.3562 0.9500 0.4083 0.039 Uiso 1 1 calc R . .
C15 C 0.1409(8) 0.8067(6) 0.3336(3) 0.0332(13) Uani 1 1 d . . .
C16 C 0.1028(8) 0.6862(7) 0.2710(4) 0.0413(15) Uani 1 1 d . . .
H16A H -0.0270 0.6360 0.2574 0.062 Uiso 1 1 calc R . .
H16B H 0.1701 0.6218 0.2904 0.062 Uiso 1 1 calc R . .
H16C H 0.1411 0.7241 0.2253 0.062 Uiso 1 1 calc R . .
C17 C 0.0398(10) 0.9082(7) 0.3017(4) 0.0483(17) Uani 1 1 d . . .
H17A H -0.0895 0.8579 0.2842 0.072 Uiso 1 1 calc R . .
H17B H 0.0866 0.9496 0.2584 0.072 Uiso 1 1 calc R . .
H17C H 0.0572 0.9823 0.3422 0.072 Uiso 1 1 calc R . .
C18 C 0.0599(10) 0.7449(7) 0.4014(4) 0.0456(16) Uani 1 1 d . . .
H18A H -0.0675 0.6908 0.3819 0.068 Uiso 1 1 calc R . .
H18B H 0.0690 0.8211 0.4391 0.068 Uiso 1 1 calc R . .
H18C H 0.1270 0.6839 0.4260 0.068 Uiso 1 1 calc R . .
C19 C 1.1999(8) 0.6249(6) -0.1224(3) 0.0314(13) Uani 1 1 d . . .
H19A H 1.1851 0.5589 -0.0832 0.047 Uiso 1 1 calc R . .
H19B H 1.3260 0.6843 -0.1119 0.047 Uiso 1 1 calc R . .
H19C H 1.1680 0.5731 -0.1733 0.047 Uiso 1 1 calc R . .
C20 C 0.8854(7) 0.6233(5) -0.1363(3) 0.0310(13) Uani 1 1 d . . .
H20A H 0.8706 0.5575 -0.0971 0.047 Uiso 1 1 calc R . .
H20B H 0.8527 0.5712 -0.1872 0.047 Uiso 1 1 calc R . .
H20C H 0.8067 0.6821 -0.1350 0.047 Uiso 1 1 calc R . .
C21 C 1.1022(8) 0.8172(5) -0.1822(3) 0.0315(13) Uani 1 1 d . . .
H21A H 1.0320 0.8823 -0.1765 0.038 Uiso 1 1 calc R . .
H21B H 1.2313 0.8732 -0.1724 0.038 Uiso 1 1 calc R . .
C22 C 1.0433(9) 0.7509(6) -0.2642(3) 0.0350(14) Uani 1 1 d . . .
C23 C 0.8656(10) 0.7297(6) -0.3040(4) 0.0446(16) Uani 1 1 d . . .
H23A H 0.7824 0.7530 -0.2788 0.054 Uiso 1 1 calc R . .
C24 C 0.8093(11) 0.6742(8) -0.3811(4) 0.0553(19) Uani 1 1 d . . .
H24A H 0.6877 0.6586 -0.4083 0.066 Uiso 1 1 calc R . .
C25 C 0.9347(11) 0.6416(8) -0.4179(4) 0.0547(19) Uani 1 1 d . . .
H25A H 0.8979 0.6038 -0.4702 0.066 Uiso 1 1 calc R . .
C26 C 1.1057(12) 0.6638(7) -0.3792(4) 0.0530(19) Uani 1 1 d . . .
H26A H 1.1900 0.6433 -0.4049 0.064 Uiso 1 1 calc R . .
C27 C 1.1626(10) 0.7167(7) -0.3019(4) 0.0448(16) Uani 1 1 d . . .
H27A H 1.2838 0.7293 -0.2751 0.054 Uiso 1 1 calc R . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 113.9(4) . . ?
C5 O2 C4 118.4(4) . . ?
C19 N1 C20 109.8(4) . . ?
C19 N1 C1 110.7(4) . . ?
C20 N1 C1 112.3(4) . . ?
C19 N1 C21 109.4(4) . . ?
C20 N1 C21 109.4(4) . . ?
C1 N1 C21 105.1(4) . . ?
O4 N2 O3 120.6(5) . . ?
O4 N2 O5 119.1(5) . . ?
O3 N2 O5 120.3(5) . . ?
C2 C1 N1 116.0(4) . . ?
O1 C2 C1 115.1(5) . . ?
O1 C3 C4 108.3(4) . . ?
O2 C4 C3 112.2(5) . . ?
O2 C5 C6 115.7(5) . . ?
O2 C5 C10 124.5(5) . . ?
C6 C5 C10 119.7(5) . . ?
C5 C6 C7 120.0(5) . . ?
C8 C7 C6 122.0(5) . . ?
C7 C8 C9 116.7(5) . . ?
C7 C8 C11 124.4(5) . . ?
C9 C8 C11 118.8(5) . . ?
C10 C9 C8 122.1(5) . . ?
C5 C10 C9 119.4(5) . . ?
C8 C11 C14 111.7(5) . . ?
C8 C11 C13 108.3(5) . . ?
C14 C11 C13 106.8(5) . . ?
C8 C11 C12 111.1(5) . . ?
C14 C11 C12 111.5(5) . . ?
C13 C11 C12 107.3(5) . . ?
C11 C14 C15 123.3(5) . . ?
C17 C15 C16 108.8(5) . . ?
C17 C15 C18 106.7(5) . . ?
C16 C15 C18 108.0(5) . . ?
C17 C15 C14 106.5(5) . . ?
C16 C15 C14 114.0(5) . . ?
C18 C15 C14 112.5(5) . . ?
C22 C21 N1 115.0(4) . . ?
C27 C22 C23 119.1(6) . . ?
C27 C22 C21 122.0(6) . . ?
C23 C22 C21 118.8(6) . . ?
C22 C23 C24 120.1(7) . . ?
C23 C24 C25 119.3(7) . . ?
C26 C25 C24 120.0(7) . . ?
C25 C26 C27 121.2(7) . . ?
C22 C27 C26 120.2(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.412(6) . ?
O1 C2 1.435(7) . ?
O2 C5 1.379(6) . ?
O2 C4 1.438(7) . ?
O3 N2 1.241(6) . ?
O4 N2 1.240(6) . ?
O5 N2 1.247(7) . ?
N1 C19 1.491(6) . ?
N1 C20 1.504(7) . ?
N1 C1 1.532(7) . ?
N1 C21 1.541(7) . ?
C1 C2 1.525(8) . ?
C3 C4 1.515(8) . ?
C5 C6 1.383(8) . ?
C5 C10 1.394(7) . ?
C6 C7 1.400(8) . ?
C7 C8 1.390(8) . ?
C8 C9 1.408(8) . ?
C8 C11 1.534(8) . ?
C9 C10 1.396(8) . ?
C11 C14 1.540(8) . ?
C11 C13 1.541(9) . ?
C11 C12 1.544(9) . ?
C14 C15 1.555(8) . ?
C15 C17 1.525(8) . ?
C15 C16 1.540(8) . ?
C15 C18 1.551(9) . ?
C21 C22 1.511(8) . ?
C22 C27 1.381(9) . ?
C22 C23 1.391(9) . ?
C23 C24 1.398(10) . ?
C24 C25 1.408(11) . ?
C25 C26 1.338(11) . ?
C26 C27 1.396(9) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B O4 0.99 2.44 3.349(7) 152.0 2_665
C27 H27A O5 0.95 2.45 3.373(9) 163.3 2_765
C21 H21A O4 0.99 2.51 3.403(7) 149.5 2_665
C20 H20C O5 0.98 2.56 3.499(8) 159.5 2_665
C1 H1A O3 0.99 2.58 3.478(7) 150.1 2_765
C21 H21B O3 0.99 2.60 3.485(8) 149.4 2_765
C19 H19B O3 0.98 2.63 3.503(7) 148.3 2_765
C19 H19B O5 0.98 2.64 3.458(8) 141.2 2_765
C3 H3A O4 0.99 2.64 3.544(8) 151.9 2_665
C4 H4B O2 1.07(5) 2.41(5) 3.398(7) 154(4) 2_665
C2 H2B O4 0.99 2.56 3.313(7) 133.3 1_665
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N1 C1 C2 -66.3(6) . . . . ?
C20 N1 C1 C2 56.8(6) . . . . ?
C21 N1 C1 C2 175.7(4) . . . . ?
C3 O1 C2 C1 -73.1(6) . . . . ?
N1 C1 C2 O1 -69.5(6) . . . . ?
C2 O1 C3 C4 165.5(4) . . . . ?
C5 O2 C4 C3 80.7(6) . . . . ?
O1 C3 C4 O2 77.5(5) . . . . ?
C4 O2 C5 C6 -170.9(5) . . . . ?
C4 O2 C5 C10 11.1(8) . . . . ?
O2 C5 C6 C7 -178.7(5) . . . . ?
C10 C5 C6 C7 -0.5(8) . . . . ?
C5 C6 C7 C8 0.6(8) . . . . ?
C6 C7 C8 C9 -0.7(8) . . . . ?
C6 C7 C8 C11 -178.8(5) . . . . ?
C7 C8 C9 C10 0.6(8) . . . . ?
C11 C8 C9 C10 178.9(5) . . . . ?
O2 C5 C10 C9 178.4(5) . . . . ?
C6 C5 C10 C9 0.5(8) . . . . ?
C8 C9 C10 C5 -0.5(8) . . . . ?
C7 C8 C11 C14 -127.8(6) . . . . ?
C9 C8 C11 C14 54.0(7) . . . . ?
C7 C8 C11 C13 114.9(6) . . . . ?
C9 C8 C11 C13 -63.3(7) . . . . ?
C7 C8 C11 C12 -2.7(8) . . . . ?
C9 C8 C11 C12 179.2(5) . . . . ?
C8 C11 C14 C15 69.4(7) . . . . ?
C13 C11 C14 C15 -172.5(5) . . . . ?
C12 C11 C14 C15 -55.6(7) . . . . ?
C11 C14 C15 C17 -162.4(5) . . . . ?
C11 C14 C15 C16 -42.4(7) . . . . ?
C11 C14 C15 C18 81.1(7) . . . . ?
C19 N1 C21 C22 64.5(6) . . . . ?
C20 N1 C21 C22 -55.8(6) . . . . ?
C1 N1 C21 C22 -176.6(5) . . . . ?
N1 C21 C22 C27 -92.4(7) . . . . ?
N1 C21 C22 C23 90.7(6) . . . . ?
C27 C22 C23 C24 0.2(9) . . . . ?
C21 C22 C23 C24 177.2(6) . . . . ?
C22 C23 C24 C25 -0.7(10) . . . . ?
C23 C24 C25 C26 0.0(11) . . . . ?
C24 C25 C26 C27 1.3(11) . . . . ?
C23 C22 C27 C26 1.0(9) . . . . ?
C21 C22 C27 C26 -175.9(5) . . . . ?
C25 C26 C27 C22 -1.8(10) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21143505
