Inclusion complexes of Cethyl-2-methylresorcinarene and pyridine N-oxides: breaking the C–I⋯−O–N+halogen bond by host–guest complexation
Puttreddy, Rakesh; Beyeh, Ngong Kodiah; Rissanen, Kari; CrystEngComm 18 (2016) 793–; doi:10.1039/C5CE02354H

data_7223615
_publ_section_title
;
 Inclusion complexes of Cethyl-2-methylresorcinarene and pyridine
 N-oxides: breaking the C--I&#x22EF;&#x2212;O--N+halogen bond by
 host--guest complexation
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              793
_journal_paper_doi               10.1039/C5CE02354H
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C40 H48 O8, C5 H4 I N O, 3(H2 O)'
_chemical_formula_sum            'C45 H58 I N O12'
_chemical_formula_weight         931.82
_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   mixed
_audit_creation_date             2015-10-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-12-17 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                95.809(3)
_cell_angle_beta                 99.751(2)
_cell_angle_gamma                106.037(2)
_cell_formula_units_Z            4
_cell_length_a                   12.4821(3)
_cell_length_b                   15.6440(5)
_cell_length_c                   23.8049(7)
_cell_measurement_reflns_used    6711
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.3740
_cell_measurement_theta_min      4.0100
_cell_volume                     4348.9(2)
_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)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -49.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1176   37.0000    0.0000 82

  2 omega    1.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1176  -99.0000  -60.0000 81

  3 omega   36.00  122.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000 -180.0000 86

  4 omega   40.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -30.0000 51

  5 omega   86.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000   30.0000 92

  6 omega  107.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000  -30.0000 70

  7 omega   80.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000  120.0000 96

  8 omega   43.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000   90.0000 48

  9 omega   29.00  138.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -77.0000  -30.0000 109

 10 omega   34.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000 -150.0000 57

 11 omega   24.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  -90.0000 85

 12 omega  -67.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1176   57.0000 -150.0000 97

 13 omega -112.00  -17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1176  -57.0000   60.0000 95
;
_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      -0.0430501000
_diffrn_orient_matrix_UB_12      0.0747018000
_diffrn_orient_matrix_UB_13      0.0267906000
_diffrn_orient_matrix_UB_21      0.0203437000
_diffrn_orient_matrix_UB_22      -0.0313107000
_diffrn_orient_matrix_UB_23      0.0591360000
_diffrn_orient_matrix_UB_31      0.1223029000
_diffrn_orient_matrix_UB_32      0.0648142000
_diffrn_orient_matrix_UB_33      0.0143170000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0949
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26293
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.747
_diffrn_reflns_theta_min         3.274
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.310
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89917
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       plate
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.1237
_exptl_crystal_size_mid          0.0712
_exptl_crystal_size_min          0.061
_refine_diff_density_max         2.883
_refine_diff_density_min         -1.658
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1098
_refine_ls_number_reflns         15297
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0722
_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^)+(0.1063P)^2^+3.2661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.2095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11065
_reflns_number_total             15297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce02354h2.cif
_cod_data_source_block           2IPyNO_1
_cod_depositor_comments
'Adding full bibliography for 7223614--7223619.cif.'
_cod_original_cell_volume        4348.8(2)
_cod_database_code               7223615
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C5 H4 N1 O1 I1'
_reflns_odcompleteness_completeness 99.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H3WA,H3WB} of O3W, {H1WA,H1WB} of O1W, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H6WA,H6WB} of O6W, {H4WA,H4WB} of O4W, {H5WA,H5WB} of
  O5W, {H2WA,H2WB} of O2W, All O(H) groups
2. Restrained distances
 O4W-H4WB
 0.82 with sigma of 0.02
 O1W-H1WA
 0.82 with sigma of 0.02
 O2W-H2WB
 0.82 with sigma of 0.02
 O6W-H6WB
 0.82 with sigma of 0.02
3.a Riding coordinates:
 O3W(H3WA,H3WB), O4W(H4WA,H4WB), O2W(H2WA,H2WB), O1W(H1WA,H1WB), O6W(H6WA,H6WB)
3.b Free rotating group:
 O5W(H5WA,H5WB)
3.c Ternary CH refined with riding coordinates:
 C7A(H7A), C14A(H14A), C21A(H21A), C28A(H28A), C7(H7), C14(H14), C21(H21),
 C28(H28)
3.d Secondary CH2 refined with riding coordinates:
 C29A(H29A,H29B), C31A(H31A,H31B), C33A(H33A,H33B), C35A(H35A,H35B), C29(H29C,
 H29D), C31(H31C,H31D), C33(H33C,H33D), C35(H35C,H35D)
3.e Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C9A(H9A), C16A(H16A), C23A(H23A), C2(H2), C9(H9), C16(H16),
 C23(H23), C1AA(H1AA), C2AA(H2AA), C3AA(H3AA), C4AA(H4AA), C3B(H3B), C4B(H4B),
 C5B(H5B), C6B(H6B)
3.f Idealised Me refined as rotating group:
 C30A(H30A,H30B,H30C), C32A(H32A,H32B,H32C), C34A(H34A,H34B,H34C), C36A(H36A,
 H36B,H36C), C37A(H37A,H37B,H37C), C38A(H38A,H38B,H38C), C39A(H39A,H39B,H39C),
 C40A(H40A,H40B,H40C), C30(H30D,H30E,H30F), C32(H32D,H32E,H32F), C34(H34D,H34E,
 H34F), C36(H36D,H36E,H36F), C37(H37D,H37E,H37F), C38(H38D,H38E,H38F), C39(H39D,
 H39E,H39F), C40(H40D,H40E,H40F)
3.g Idealised tetrahedral OH refined as rotating group:
 O4A(H4A), O6A(H6A), O11A(H11A), O13A(H13A), O18A(H18A), O20A(H20A),
 O25A(H25A), O27A(H27A), O4(H4), O6(H6), O11(H11), O13(H13), O18(H18), O20(H20),
  O25(H25), O27(H27)
;
_shelx_res_checksum              45675
_olex2_submission_special_instructions 'No special instructions were received'