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_7223619
_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, 2(C5 H11 N O2), 2(C H4 O)'
_chemical_formula_sum            'C52 H78 N2 O14'
_chemical_formula_weight         955.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 103.57(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.672(3)
_cell_length_b                   24.549(5)
_cell_length_c                   16.932(3)
_cell_measurement_temperature    170
_cell_volume                     5120.2(19)
_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_temperature      170
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1021
_diffrn_reflns_av_unetI/netI     0.1190
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            62678
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         1.653
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0747 after correction.
The Ratio of minimum to maximum transmission is 0.8288.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.927
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     638
_refine_ls_number_reflns         9271
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1208P)^2^+1.9749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5957
_reflns_number_total             9271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce02354h2.cif
_cod_data_source_block           NMO_1
_cod_depositor_comments
'Adding full bibliography for 7223614--7223619.cif.'
_cod_original_cell_volume        5120.1(19)
_cod_database_code               7223619
_shelxl_version_number           2013-4
_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, All O(H) groups
2. Restrained distances
 H2S-O2S
 0.82 with sigma of 0.02
 C2S-O2S
 1.43 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C1S) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C2S) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
4.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C31(H31A,H31B), C33(H33A,H33B), C35(H35A,H35B), C2B(H2BA,
 H2BB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C2A(H2AA,H2AB),
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C16(H16), C23(H23)
4.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,
 H40B,H40C), C1B(H1BA,H1BB,H1BC), C1A(H1AA,H1AB,H1AC), C1S(H1SA,H1SB,H1SC),
 C2S(H2SA,H2SB,H2SC)
4.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O8(H8), O11(H11), O13(H13), O18(H18), O20(H20), O27(H27),
 O1S(H1S)
;
_shelx_res_checksum              1809
_olex2_submission_special_instructions 'No special instructions were received'