Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides.
Beyeh, Ngong Kodiah; Jo, Hyun Hwa; Kolesnichenko, Igor; Pan, Fangfang; Kalenius, Elina; Anslyn, Eric V.; Ras, Robin H. A.; Rissanen, Kari; The Journal of organic chemistry 82 (2017) 5198–5203; doi:10.1021/acs.joc.7b00449

data_4032490
_publ_section_title
;
 Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium
 Resorcinarene Chlorides.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5198
_journal_page_last               5203
_journal_paper_doi               10.1021/acs.joc.7b00449
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         '2.62(I), C14 H16 N2 O, 0.3(Cl)'
_chemical_formula_sum            'C14 H16 Cl0.3 I2.62 N2 O'
_chemical_formula_weight         571.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                94.825(7)
_cell_angle_beta                 97.934(9)
_cell_angle_gamma                92.335(7)
_cell_formula_units_Z            2
_cell_length_a                   8.6240(9)
_cell_length_b                   9.7739(6)
_cell_length_c                   10.9703(13)
_cell_measurement_reflns_used    2137
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      28.9110
_cell_measurement_theta_min      3.2540
_cell_volume                     911.31(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -89.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6055  -19.0000  120.0000 112

  2 omega  -43.00   11.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6055  -77.0000  -30.0000 54

  3 omega  -81.00   -1.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6055  -57.0000   60.0000 80

  4 omega  -40.00   45.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6055   57.0000  -60.0000 85

  5 omega   20.00   62.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6993  -99.0000 -150.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0790160000
_diffrn_orient_matrix_UB_12      -0.0093616000
_diffrn_orient_matrix_UB_13      -0.0086269000
_diffrn_orient_matrix_UB_21      -0.0165289000
_diffrn_orient_matrix_UB_22      0.0198207000
_diffrn_orient_matrix_UB_23      -0.0609810000
_diffrn_orient_matrix_UB_31      0.0199692000
_diffrn_orient_matrix_UB_32      0.0695594000
_diffrn_orient_matrix_UB_33      0.0224471000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5437
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         3.092
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.543
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.082
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.2426
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.0419
_refine_diff_density_max         1.737
_refine_diff_density_min         -1.421
_refine_diff_density_rms         0.234
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0492
_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/[\s^2^(Fo^2^)+(0.0599P)^2^+1.4992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2828
_reflns_number_total             3285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00449_si_004.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 4032490--4032491.cif.'
_cod_original_cell_volume        911.30(16)
_cod_original_formula_sum        'C14 H16 Cl0.30 I2.62 N2 O'
_cod_database_code               4032490
_chemical_oxdiff_formula         'C50 H100 N4 O8 Cl4 I1'
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Shared sites
{Cl3, I3}
3. Uiso/Uaniso restraints and constraints
Uanis(Cl3) = Uanis(I3)
4. Others
 Fixed Sof: I4(0.42) I3(0.7) Cl3(0.3)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C4(H4), C7(H7), C5(H5), C8(H8), C1(H1), C2(H2)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'