#------------------------------------------------------------------------------
#$Date: 2020-04-05 14:10:23 +0300 (Sun, 05 Apr 2020) $
#$Revision: 250358 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/73/7157355.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_7157355
loop_
_publ_author_name
'Konstandaras, Nicholas'
'Dunn, Michelle H.'
'Luis, Ena T.'
'Cole, Marcus L.'
'Harper, Jason B.'
_publ_section_title
;
 The pKₐ values of N-aryl imidazolinium salts, their higher
 homologues, and formamidinium salts in dimethyl sulfoxide.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1910
_journal_page_last               1917
_journal_paper_doi               10.1039/d0ob00036a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C19.50 H26 Cl I N2'
_chemical_formula_sum            'C19.5 H26 Cl I N2'
_chemical_formula_weight         450.77
_chemical_name_common            '166-B.HI half dichloromethane solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-12-20 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 124.7010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.6780(5)
_cell_length_b                   26.8240(8)
_cell_length_c                   11.0601(3)
_cell_measurement_reflns_used    5670
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.533
_cell_measurement_theta_min      1.668
_cell_volume                     4067.9(2)
_computing_cell_refinement       'Bruker Apex II software'
_computing_data_collection       'Bruker Apex II software'
_computing_data_reduction        X-Seed
_computing_molecular_graphics    'X-Seed / POV-Ray'
_computing_publication_material  'Microsoft Office 2010'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18215
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.533
_diffrn_reflns_theta_min         1.668
_diffrn_source                   'Bruker Quazar Multilayer Optics'
_exptl_absorpt_coefficient_mu    1.709
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       'trapezoid plate'
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0248P)²+5.9758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0689
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4646
_reflns_number_total             5670
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00036a2.cif
_cod_data_source_block           21
_cod_depositor_comments
'Adding full bibliography for 7157354--7157355.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C19.50 H26 Cl I N2'
_cod_database_code               7157355
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.784
_shelx_estimated_absorpt_t_max   0.967
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.5000 0.38659(2) 0.7500 0.03700(7) Uani 1 2 d S T P . .
I2 I 0.0000 0.30143(2) 0.7500 0.02799(6) Uani 1 2 d S T P . .
Cl1S Cl 0.02724(10) 0.52899(4) 0.14657(13) 0.0874(3) Uani 1 1 d . . . . .
N1 N 0.22028(13) 0.35825(6) 0.2907(2) 0.0223(4) Uani 1 1 d . . . . .
N2 N 0.36937(13) 0.35873(6) 0.30745(19) 0.0203(3) Uani 1 1 d . . . . .
C1 C 0.31267(16) 0.34781(8) 0.3508(2) 0.0209(4) Uani 1 1 d . . . . .
C1S C 0.0392(6) 0.5586(2) 0.2880(10) 0.070(2) Uani 0.5 1 d . . P . .
H1S1 H 0.0156 0.5932 0.2584 0.084 Uiso 0.5 1 calc R U P . .
H1S2 H 0.1092 0.5600 0.3697 0.084 Uiso 0.5 1 calc R U P . .
H1 H 0.3420(16) 0.3312(8) 0.436(3) 0.014(5) Uiso 1 1 d . . . . .
H5 H 0.090(2) 0.2344(11) 0.384(3) 0.048(9) Uiso 1 1 d . . . . .
H15 H 0.357(2) 0.4977(11) 0.086(3) 0.045(8) Uiso 1 1 d . . . . .
H18A H 0.422(2) 0.4968(12) 0.343(4) 0.054(9) Uiso 1 1 d . . . . .
H19A H 0.130(2) 0.3658(10) 0.066(3) 0.042(8) Uiso 1 1 d . . . . .
H9A H 0.129(2) 0.2695(10) 0.136(3) 0.037(7) Uiso 1 1 d . . . . .
H19B H 0.180(2) 0.4145(11) 0.148(4) 0.048(9) Uiso 1 1 d . . . . .
H10A H 0.174(2) 0.4359(12) 0.537(4) 0.063(10) Uiso 1 1 d . . . . .
H18B H 0.370(2) 0.4596(11) 0.380(4) 0.058(9) Uiso 1 1 d . . . . .
H19C H 0.095(3) 0.3949(11) 0.147(4) 0.054(9) Uiso 1 1 d . . . . .
H2A H 0.473(2) 0.3102(11) 0.342(4) 0.053(9) Uiso 1 1 d . . . . .
H7 H 0.104(2) 0.3656(10) 0.566(3) 0.041(7) Uiso 1 1 d . . . . .
H9B H 0.228(2) 0.2523(10) 0.269(3) 0.038(7) Uiso 1 1 d . . . . .
H2B H 0.512(2) 0.3646(10) 0.401(3) 0.041(8) Uiso 1 1 d . . . . .
H2C H 0.488(2) 0.3305(10) 0.487(3) 0.043(8) Uiso 1 1 d . . . . .
H14 H 0.281(2) 0.4590(12) -0.143(4) 0.058(9) Uiso 1 1 d . . . . .
H9C H 0.140(2) 0.2224(12) 0.226(4) 0.054(9) Uiso 1 1 d . . . . .
H13 H 0.248(2) 0.3736(11) -0.172(4) 0.047(8) Uiso 1 1 d . . . . .
H10B H 0.167(3) 0.4379(13) 0.385(4) 0.070(11) Uiso 1 1 d . . . . .
H6 H 0.062(2) 0.2820(11) 0.533(3) 0.050(8) Uiso 1 1 d . . . . .
H10C H 0.254(3) 0.4229(13) 0.522(4) 0.058(11) Uiso 1 1 d . . . . .
H18C H 0.473(3) 0.4470(12) 0.414(4) 0.058(10) Uiso 1 1 d . . . . .
H17A H 0.237(3) 0.2986(11) 0.047(4) 0.062(10) Uiso 1 1 d . . . . .
H17B H 0.335(3) 0.2900(14) 0.088(5) 0.079(13) Uiso 1 1 d . . . . .
H17C H 0.252(3) 0.2973(13) -0.069(5) 0.079(12) Uiso 1 1 d . . . . .
C2 C 0.47035(17) 0.33951(10) 0.3951(3) 0.0295(5) Uani 1 1 d . . . . .
C3 C 0.17673(16) 0.33630(8) 0.3611(2) 0.0241(4) Uani 1 1 d . . . . .
C4 C 0.14923(16) 0.28634(9) 0.3330(2) 0.0265(5) Uani 1 1 d . . . . .
C5 C 0.10673(18) 0.26626(11) 0.4001(3) 0.0341(5) Uani 1 1 d . . . . .
C6 C 0.09190(18) 0.29499(11) 0.4888(3) 0.0401(7) Uani 1 1 d . . . . .
C7 C 0.11904(18) 0.34419(12) 0.5132(3) 0.0384(6) Uani 1 1 d . . . . .
C8 C 0.16286(17) 0.36636(10) 0.4506(3) 0.0314(5) Uani 1 1 d . . . . .
C9 C 0.1618(2) 0.25489(10) 0.2326(3) 0.0320(5) Uani 1 1 d . . . . .
C10 C 0.1961(3) 0.41934(12) 0.4818(4) 0.0446(7) Uani 1 1 d . . . . .
C11 C 0.34265(15) 0.38720(7) 0.1787(2) 0.0201(4) Uani 1 1 d . . . . .
C12 C 0.30237(15) 0.36255(8) 0.0458(2) 0.0232(4) Uani 1 1 d . . . . .
C13 C 0.2805(2) 0.39088(10) -0.0748(3) 0.0360(6) Uani 1 1 d . . . . .
C14 C 0.3002(2) 0.44122(11) -0.0599(3) 0.0460(7) Uani 1 1 d . . . . .
C15 C 0.3423(2) 0.46462(10) 0.0736(3) 0.0417(6) Uani 1 1 d . . . . .
C16 C 0.36498(17) 0.43801(8) 0.1973(3) 0.0269(5) Uani 1 1 d . . . . .
C17 C 0.2839(2) 0.30771(9) 0.0310(3) 0.0309(5) Uani 1 1 d . . . . .
C18 C 0.4104(2) 0.46288(10) 0.3437(4) 0.0422(7) Uani 1 1 d . . . . .
C19 C 0.15381(18) 0.38568(10) 0.1532(3) 0.0291(5) 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C1S Cl1S C1S 35.8(5) . 2 ?
C1 N1 C3 116.16(18) . . ?
C1 N1 C19 127.28(17) . . ?
C3 N1 C19 116.30(17) . . ?
C1 N2 C11 126.53(18) . . ?
C1 N2 C2 118.12(19) . . ?
C11 N2 C2 115.33(16) . . ?
N2 C1 N1 130.4(2) . . ?
N2 C1 H1 114.9(14) . . ?
N1 C1 H1 114.7(14) . . ?
Cl1S C1S Cl1S 113.2(4) . 2 ?
Cl1S C1S H1S1 108.9 . . ?
Cl1S C1S H1S1 108.9 2 . ?
Cl1S C1S H1S2 108.9 . . ?
Cl1S C1S H1S2 108.9 2 . ?
H1S1 C1S H1S2 107.8 . . ?
N2 C2 H2A 107.8(19) . . ?
N2 C2 H2B 108.3(18) . . ?
H2A C2 H2B 109(2) . . ?
N2 C2 H2C 110.6(18) . . ?
H2A C2 H2C 110(2) . . ?
H2B C2 H2C 110(3) . . ?
C4 C3 C8 123.25(19) . . ?
C4 C3 N1 118.05(18) . . ?
C8 C3 N1 118.69(19) . . ?
C5 C4 C3 117.1(2) . . ?
C5 C4 C9 120.3(2) . . ?
C3 C4 C9 122.59(19) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 121.0(19) . . ?
C4 C5 H5 117.9(19) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 117.7(18) . . ?
C5 C6 H6 121.9(18) . . ?
C6 C7 C8 121.3(2) . . ?
C6 C7 H7 122.4(17) . . ?
C8 C7 H7 116.1(17) . . ?
C3 C8 C7 116.8(2) . . ?
C3 C8 C10 121.7(2) . . ?
C7 C8 C10 121.5(2) . . ?
C4 C9 H9A 110.9(16) . . ?
C4 C9 H9B 110.5(17) . . ?
H9A C9 H9B 107(2) . . ?
C4 C9 H9C 112.1(19) . . ?
H9A C9 H9C 110(3) . . ?
H9B C9 H9C 106(2) . . ?
C8 C10 H10A 110.5(19) . . ?
C8 C10 H10B 109(2) . . ?
H10A C10 H10B 109(3) . . ?
C8 C10 H10C 114(3) . . ?
H10A C10 H10C 111(3) . . ?
H10B C10 H10C 103(3) . . ?
C12 C11 C16 123.3(2) . . ?
C12 C11 N2 118.95(18) . . ?
C16 C11 N2 117.63(19) . . ?
C11 C12 C13 117.4(2) . . ?
C11 C12 C17 122.1(2) . . ?
C13 C12 C17 120.6(2) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 122.0(17) . . ?
C12 C13 H13 117.6(17) . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 121(2) . . ?
C13 C14 H14 118(2) . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 122.2(19) . . ?
C16 C15 H15 117.2(19) . . ?
C15 C16 C11 117.1(2) . . ?
C15 C16 C18 121.4(2) . . ?
C11 C16 C18 121.5(2) . . ?
C12 C17 H17A 112.4(19) . . ?
C12 C17 H17B 114(3) . . ?
H17A C17 H17B 108(3) . . ?
C12 C17 H17C 111(2) . . ?
H17A C17 H17C 100(3) . . ?
H17B C17 H17C 111(3) . . ?
C16 C18 H18A 114(2) . . ?
C16 C18 H18B 112(2) . . ?
H18A C18 H18B 107(3) . . ?
C16 C18 H18C 108.6(19) . . ?
H18A C18 H18C 107(3) . . ?
H18B C18 H18C 108(3) . . ?
N1 C19 H19A 113.3(17) . . ?
N1 C19 H19B 113(2) . . ?
H19A C19 H19B 111(3) . . ?
N1 C19 H19C 109.7(19) . . ?
H19A C19 H19C 104(3) . . ?
H19B C19 H19C 106(3) . . ?
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
Cl1S C1S 1.662(8) . ?
Cl1S C1S 1.815(8) 2 ?
N1 C1 1.315(3) . ?
N1 C3 1.458(2) . ?
N1 C19 1.471(3) . ?
N2 C1 1.314(2) . ?
N2 C11 1.445(3) . ?
N2 C2 1.477(3) . ?
C1 H1 0.90(2) . ?
C1S Cl1S 1.815(8) 2 ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2 H2A 1.00(3) . ?
C2 H2B 0.94(3) . ?
C2 H2C 0.92(3) . ?
C3 C4 1.393(3) . ?
C3 C8 1.394(3) . ?
C4 C5 1.393(3) . ?
C4 C9 1.502(3) . ?
C5 C6 1.376(4) . ?
C5 H5 0.89(3) . ?
C6 C7 1.371(4) . ?
C6 H6 0.94(3) . ?
C7 C8 1.394(3) . ?
C7 H7 0.94(3) . ?
C8 C10 1.493(4) . ?
C9 H9A 0.96(3) . ?
C9 H9B 0.94(3) . ?
C9 H9C 0.93(3) . ?
C10 H10A 0.99(3) . ?
C10 H10B 1.02(4) . ?
C10 H10C 0.80(4) . ?
C11 C12 1.388(3) . ?
C11 C16 1.397(3) . ?
C12 C13 1.391(3) . ?
C12 C17 1.493(3) . ?
C13 C14 1.378(4) . ?
C13 H13 1.00(3) . ?
C14 C15 1.373(4) . ?
C14 H14 0.92(3) . ?
C15 C16 1.392(4) . ?
C15 H15 0.91(3) . ?
C16 C18 1.498(4) . ?
C17 H17A 0.93(3) . ?
C17 H17B 0.86(4) . ?
C17 H17C 0.96(4) . ?
C18 H18A 0.93(3) . ?
C18 H18B 0.97(3) . ?
C18 H18C 0.98(3) . ?
C19 H19A 0.96(3) . ?
C19 H19B 0.90(3) . ?
C19 H19C 0.97(3) . ?
