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_4032491
_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         'C11 H12 N2, C11 H11 N2, I3, 2(I)'
_chemical_formula_sum            'C22 H23 I5 N4'
_chemical_formula_weight         977.94
_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                68.296(4)
_cell_angle_beta                 78.859(3)
_cell_angle_gamma                84.254(3)
_cell_formula_units_Z            6
_cell_length_a                   9.8611(3)
_cell_length_b                   21.0117(8)
_cell_length_c                   22.6116(10)
_cell_measurement_reflns_used    5864
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      72.6070
_cell_measurement_theta_min      3.6060
_cell_volume                     4268.8(3)
_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      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
  1 omega -115.00  -14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000    0.0000 101

  2 omega  -49.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  150.0000 82

  3 omega    1.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013  -99.0000 -120.0000 82

  4 omega   29.00   91.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000   90.0000 62

  5 omega   54.00  119.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818 -125.0000    0.0000 65

  6 omega   22.00  108.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -94.0000   60.0000 86

  7 omega  101.00  157.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -15.0000 -120.0000 56

  8 omega   23.00   94.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -15.0000 -120.0000 71

  9 omega   46.00  109.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -94.0000  150.0000 63

 10 omega   33.00  128.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -61.0000 -180.0000 95

 11 omega   95.00  175.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  125.0000  120.0000 80

 12 omega   29.00   90.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000   30.0000 61

 13 omega   86.00  152.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   61.0000 -120.0000 66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0364029000
_diffrn_orient_matrix_UB_12      -0.0167273000
_diffrn_orient_matrix_UB_13      0.0675256000
_diffrn_orient_matrix_UB_21      -0.0542335000
_diffrn_orient_matrix_UB_22      -0.0727587000
_diffrn_orient_matrix_UB_23      0.0214697000
_diffrn_orient_matrix_UB_31      0.1452989000
_diffrn_orient_matrix_UB_32      -0.0256887000
_diffrn_orient_matrix_UB_33      -0.0226873000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.1035
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26325
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.440
_diffrn_reflns_theta_min         3.628
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    43.036
_exptl_absorpt_correction_T_max  0.762
_exptl_absorpt_correction_T_min  0.585
_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    2.282
_exptl_crystal_description       block
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.0525
_exptl_crystal_size_mid          0.0324
_exptl_crystal_size_min          0.0204
_refine_diff_density_max         1.054
_refine_diff_density_min         -1.552
_refine_diff_density_rms         0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     844
_refine_ls_number_reflns         16350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0115P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11443
_reflns_number_total             16350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00449_si_003.cif
_cod_data_source_block           9b
_cod_depositor_comments
;
Adding full bibliography for 4032490--4032491.cif.

2020-07-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '3(C11 H12 N2), 3(C11 H11 N2), 5(I3)'
_cod_original_formula_sum        'C66 H69 I15 N12'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     2933.83
_cod_database_code               4032491
_chemical_oxdiff_formula         'C50 h50 O8 N4 Cl4 I2'
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N11(H11), C56(H56), C57(H57), C59(H59), C60(H60), C62(H62), C63(H63),
 C64(H64), C65(H65), N9(H9), C45(H45), C46(H46), C48(H48), C49(H49), C51(H51),
 C52(H52), C53(H53), C54(H54), N1(H1), C1(H1A), C2(H2), C4(H4), C5(H5), C7(H7),
 C8(H8), C9(H9A), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21), C34(H34), C35(H35), C37(H37), C38(H38), C40(H40),
  C41(H41), C42(H42), C43(H43), C23(H23), C24(H24), C26(H26), C27(H27),
 C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C55(H55A,H55B,H55C), C11(H11A,H11B,H11C), C22(H22A,H22B,
 H22C), C44(H44A,H44B,H44C), C33(H33A,H33B,H33C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'