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_4032522
_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         'I, C11 H11 N2'
_chemical_formula_sum            'C11 H11 I N2'
_chemical_formula_weight         298.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3855(2)
_cell_length_b                   7.36310(9)
_cell_length_c                   18.7465(3)
_cell_measurement_reflns_used    23681
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      29.5140
_cell_measurement_theta_min      3.2170
_cell_volume                     2261.73(5)
_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      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega  -45.00   53.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5946   37.0000  120.0000 98

  2 omega  -41.00   49.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5946   57.0000 -150.0000 90

  3 omega  -84.00  -36.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5946 -178.0000  -90.0000 48

  4 omega   -8.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883   77.0000  -30.0000 99

  5 omega    3.00   89.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883   57.0000   90.0000 86

  6 omega  -48.00   37.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883  -57.0000  -60.0000 85

  7 omega   -9.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883   77.0000 -180.0000 100

  8 omega   10.00   89.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883   57.0000 -120.0000 79

  9 omega   35.00   79.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883 -126.0000  102.8763 44

 10 omega   16.00   81.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883 -129.0000  -93.5269 65

 11 omega  -88.00    2.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5946  -57.0000 -180.0000 90

 12 omega  -96.00  -35.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5946 -178.0000  150.0000 61

 13 omega  -20.00   63.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883  -99.0000  -30.0000 83

 14 omega   -1.00   89.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883   57.0000   60.0000 90

 15 omega    5.00   81.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883 -129.0000 -158.8284 76

 16 omega   -9.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883   77.0000  -60.0000 100

 17 omega   34.00   97.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883 -178.0000   90.0000 63

 18 omega   -1.00   89.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.6883   57.0000  150.0000 90

 19 omega  -96.00  -71.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5946 -178.0000  120.0000 25
;
_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      0.0015143000
_diffrn_orient_matrix_UB_12      -0.0188294000
_diffrn_orient_matrix_UB_13      0.0370747000
_diffrn_orient_matrix_UB_21      0.0431163000
_diffrn_orient_matrix_UB_22      -0.0070048000
_diffrn_orient_matrix_UB_23      -0.0019177000
_diffrn_orient_matrix_UB_31      0.0035074000
_diffrn_orient_matrix_UB_32      0.0942471000
_diffrn_orient_matrix_UB_33      0.0072525000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            64350
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.614
_diffrn_reflns_theta_min         3.222
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.795
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.931
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.6719
_exptl_crystal_size_mid          0.0938
_exptl_crystal_size_min          0.0805
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0135P)^2^+8.2467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2733
_reflns_number_total             3089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00449_si_002.cif
_cod_data_source_block           9
_cod_original_cell_volume        2261.74(6)
_cod_database_code               4032522
_chemical_oxdiff_formula         'C50 H100 N4 O12 S4 I1'
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C10(H10), C5(H5), C9(H9), C1(H1), C7(H7)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'