#------------------------------------------------------------------------------
#$Date: 2017-06-05 03:35:01 +0300 (Mon, 05 Jun 2017) $
#$Revision: 197454 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/24/4032490.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_4032490
loop_
_publ_author_name
'Beyeh, Ngong Kodiah'
'Jo, Hyun Hwa'
'Kolesnichenko, Igor'
'Pan, Fangfang'
'Kalenius, Elina'
'Anslyn, Eric V.'
'Ras, Robin H. A.'
'Rissanen, Kari'
_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
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -89.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6055  -19.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00   11.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6055  -77.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega  -81.00   -1.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6055  -57.0000   60.0000 80

#__ type_ start__ end____ width___ exp.time_
  4 omega  -40.00   45.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.6055   57.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
  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       'ω 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/[σ²(Fo²)+(0.0599P)²+1.4992P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_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.
;
_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'
loop_
_space_group_symop_operation_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_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 1.38552(6) 0.42982(5) 0.72724(5) 0.02567(19) Uani 1 1 d . . . . .
I2 I 1.0000 0.0000 1.0000 0.0314(2) Uani 1 2 d S T P . .
I4 I 0.5000 0.0000 0.5000 0.0213(2) Uani 0.84 2 d S T P A 1
I3 I 0.64758(8) 0.05307(6) 0.28189(6) 0.0253(2) Uani 0.7 1 d . . . A 1
O20 O 0.8637(6) 0.3802(5) 0.8963(5) 0.0272(13) Uani 1 1 d . . . . .
N1 N 0.8227(7) 0.2217(6) 0.6793(6) 0.0208(14) Uani 1 1 d . . . . .
N2 N 1.2051(8) 0.3244(6) 0.1731(6) 0.0225(15) Uani 1 1 d . . . . .
C6 C 1.0657(9) 0.2992(7) 0.3814(7) 0.0206(17) Uani 1 1 d . . . . .
C10 C 1.2263(10) 0.2825(9) 0.3827(8) 0.031(2) Uani 1 1 d . . . . .
H10 H 1.2876 0.2632 0.4552 0.037 Uiso 1 1 calc R . . . .
C9 C 1.2936(10) 0.2944(9) 0.2778(8) 0.0296(19) Uani 1 1 d . . . . .
H9 H 1.4000 0.2818 0.2787 0.035 Uiso 1 1 calc R . . . .
C3 C 0.9861(9) 0.2796(8) 0.4909(7) 0.0229(17) Uani 1 1 d . . . . .
C14 C 1.2778(10) 0.3288(9) 0.0589(8) 0.0281(19) Uani 1 1 d . . . . .
H14A H 1.3742 0.3840 0.0763 0.042 Uiso 1 1 calc GR . . . .
H14B H 1.2076 0.3679 -0.0029 0.042 Uiso 1 1 calc GR . . . .
H14C H 1.2988 0.2371 0.0292 0.042 Uiso 1 1 calc GR . . . .
C4 C 1.0445(9) 0.1906(8) 0.5766(8) 0.0264(18) Uani 1 1 d . . . . .
H4 H 1.1397 0.1508 0.5709 0.032 Uiso 1 1 calc R . . . .
C12 C 0.7650(9) 0.2891(8) 0.8890(7) 0.0212(17) Uani 1 1 d . . . . .
C7 C 0.9804(10) 0.3320(8) 0.2727(8) 0.0248(18) Uani 1 1 d . . . . .
H7 H 0.8738 0.3453 0.2692 0.030 Uiso 1 1 calc R . . . .
C5 C 0.9601(9) 0.1620(8) 0.6698(8) 0.0257(18) Uani 1 1 d . . . . .
H5 H 0.9975 0.1014 0.7266 0.031 Uiso 1 1 calc R . . . .
C11 C 0.7290(9) 0.1871(8) 0.7765(7) 0.0225(17) Uani 1 1 d . . . . .
H11A H 0.7517 0.0956 0.7997 0.027 Uiso 1 1 calc R . . . .
H11B H 0.6183 0.1867 0.7445 0.027 Uiso 1 1 calc R . . . .
C13 C 0.6678(10) 0.2622(9) 0.9898(7) 0.0266(18) Uani 1 1 d . . . . .
H13A H 0.7128 0.1914 1.0368 0.040 Uiso 1 1 calc GR . . . .
H13B H 0.5627 0.2331 0.9534 0.040 Uiso 1 1 calc GR . . . .
H13C H 0.6660 0.3449 1.0433 0.040 Uiso 1 1 calc GR . . . .
C8 C 1.0527(9) 0.3450(7) 0.1692(7) 0.0222(17) Uani 1 1 d . . . . .
H8 H 0.9949 0.3683 0.0966 0.027 Uiso 1 1 calc R . . . .
C1 C 0.7698(9) 0.3135(8) 0.6011(7) 0.0226(17) Uani 1 1 d . . . . .
H1 H 0.6782 0.3573 0.6117 0.027 Uiso 1 1 calc R . . . .
C2 C 0.8486(10) 0.3429(8) 0.5069(8) 0.0254(18) Uani 1 1 d . . . . .
H2 H 0.8101 0.4059 0.4528 0.031 Uiso 1 1 calc R . . . .
Cl3 Cl 0.64758(8) 0.05307(6) 0.28189(6) 0.0253(2) Uani 0.3 1 d . . . B 2
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'
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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -13 -5 0.0717 0.0086 -13.0004 -4.9910 0.1654 0.0465 -1.0162
-12 -3 4 0.0990 -11.9986 -3.0053 4.0015 -0.9545 -0.1053 -0.3588
11 -5 -6 0.1197 11.0042 -4.9956 -5.9963 0.9680 0.0848 -0.2623
3 2 14 0.0169 3.0048 1.9966 13.9920 0.0980 -0.8633 0.5130
-3 -1 -14 0.0195 -3.0056 -0.9964 -13.9926 -0.1075 0.8832 -0.4434
7 -4 11 0.0496 7.0094 -4.0022 10.9959 0.4965 -0.8657 0.1084
4 -12 6 0.0712 4.0133 -12.0027 6.0028 0.3777 -0.6703 -0.6200
5 12 2 0.0565 4.9921 12.0027 1.9921 0.2649 0.0339 0.9793
-12 2 7 0.0967 -12.0015 1.9945 6.9975 -1.0274 -0.1888 0.0562
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_3
I3 I4 I3 180.0 2_656
C5 N1 C11 120.3(7) .
C1 N1 C5 120.7(7) .
C1 N1 C11 118.9(7) .
C9 N2 C14 119.1(7) .
C8 N2 C9 121.5(7) .
C8 N2 C14 119.4(7) .
C10 C6 C3 122.2(7) .
C7 C6 C10 117.7(7) .
C7 C6 C3 120.1(7) .
C6 C10 H10 119.8 .
C9 C10 C6 120.3(8) .
C9 C10 H10 119.8 .
N2 C9 C10 119.9(8) .
N2 C9 H9 120.1 .
C10 C9 H9 120.1 .
C4 C3 C6 120.2(7) .
C2 C3 C6 121.3(7) .
C2 C3 C4 118.5(8) .
N2 C14 H14A 109.5 .
N2 C14 H14B 109.5 .
N2 C14 H14C 109.5 .
H14A C14 H14B 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C3 C4 H4 120.3 .
C5 C4 C3 119.4(8) .
C5 C4 H4 120.3 .
O20 C12 C11 122.1(7) .
O20 C12 C13 124.4(7) .
C11 C12 C13 113.5(6) .
C6 C7 H7 119.9 .
C6 C7 C8 120.3(8) .
C8 C7 H7 119.9 .
N1 C5 C4 120.3(7) .
N1 C5 H5 119.8 .
C4 C5 H5 119.8 .
N1 C11 C12 111.1(6) .
N1 C11 H11A 109.4 .
N1 C11 H11B 109.4 .
C12 C11 H11A 109.4 .
C12 C11 H11B 109.4 .
H11A C11 H11B 108.0 .
C12 C13 H13A 109.5 .
C12 C13 H13B 109.5 .
C12 C13 H13C 109.5 .
H13A C13 H13B 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
N2 C8 C7 120.2(8) .
N2 C8 H8 119.9 .
C7 C8 H8 119.9 .
N1 C1 H1 119.7 .
N1 C1 C2 120.7(8) .
C2 C1 H1 119.7 .
C3 C2 H2 119.9 .
C1 C2 C3 120.3(8) .
C1 C2 H2 119.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I4 I3 2.9343(7) .
I4 I3 2.9343(7) 2_656
O20 C12 1.196(9) .
N1 C5 1.354(10) .
N1 C11 1.478(9) .
N1 C1 1.342(10) .
N2 C9 1.349(11) .
N2 C14 1.479(10) .
N2 C8 1.333(10) .
C6 C10 1.399(11) .
C6 C3 1.485(10) .
C6 C7 1.381(11) .
C10 H10 0.9300 .
C10 C9 1.370(12) .
C9 H9 0.9300 .
C3 C4 1.391(11) .
C3 C2 1.386(11) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C4 H4 0.9300 .
C4 C5 1.375(11) .
C12 C11 1.508(11) .
C12 C13 1.511(11) .
C7 H7 0.9300 .
C7 C8 1.381(11) .
C5 H5 0.9300 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C8 H8 0.9300 .
C1 H1 0.9300 .
C1 C2 1.357(11) .
C2 H2 0.9300 .
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
O20 C12 C11 N1 -3.7(11)
N1 C1 C2 C3 -0.7(12)
C6 C10 C9 N2 1.0(13)
C6 C3 C4 C5 -172.9(7)
C6 C3 C2 C1 173.7(7)
C6 C7 C8 N2 0.8(11)
C10 C6 C3 C4 -27.8(11)
C10 C6 C3 C2 155.6(8)
C10 C6 C7 C8 1.1(11)
C9 N2 C8 C7 -1.9(11)
C3 C6 C10 C9 176.5(7)
C3 C6 C7 C8 -177.5(7)
C3 C4 C5 N1 -1.1(12)
C14 N2 C9 C10 -176.4(7)
C14 N2 C8 C7 175.5(7)
C4 C3 C2 C1 -2.9(12)
C7 C6 C10 C9 -2.0(12)
C7 C6 C3 C4 150.6(8)
C7 C6 C3 C2 -25.9(11)
C5 N1 C11 C12 94.9(8)
C5 N1 C1 C2 3.5(12)
C11 N1 C5 C4 177.7(7)
C11 N1 C1 C2 -176.8(7)
C13 C12 C11 N1 177.7(7)
C8 N2 C9 C10 1.0(12)
C1 N1 C5 C4 -2.6(11)
C1 N1 C11 C12 -84.9(8)
C2 C3 C4 C5 3.8(12)
