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_7223617
_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
'2(C40 H48 O8), 3(C6 H7 N O), C6 H6 N O, 3(C H4 O)'
_chemical_formula_sum            'C107 H135 N4 O23'
_chemical_formula_weight         1845.18
_chemical_name_systematic
;
 ?
;
_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             2015-10-30
_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                76.17(3)
_cell_angle_beta                 75.84(3)
_cell_angle_gamma                84.38(3)
_cell_formula_units_Z            1
_cell_length_a                   11.929(2)
_cell_length_b                   12.698(3)
_cell_length_c                   17.705(4)
_cell_measurement_temperature    170.0
_cell_volume                     2522.8(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0720
_diffrn_reflns_av_unetI/netI     0.0971
_diffrn_reflns_laue_measured_fraction_full 0.984
_diffrn_reflns_laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23220
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         1.762
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0899 before and 0.0743 after correction.
The Ratio of minimum to maximum transmission is 0.7125.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       plate
_exptl_crystal_F_000             989
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         8975
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.0979
_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^)+(0.1293P)^2^+4.9790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2502
_refine_ls_wR_factor_ref         0.2987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5129
_reflns_number_total             8975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce02354h2.cif
_cod_data_source_block           3MePyNO_1
_cod_depositor_comments
'Adding full bibliography for 7223614--7223619.cif.'
_cod_database_code               7223617
_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
 C2S-O2S
 1.43 with sigma of 0.01
 C1S-O1S
 1.43 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C36) \\sim Ueq, Uanis(C6A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: C2B(0.5) H2B(0.5) C3B(0.5) C4B(0.5) H4B(0.5) C5B(0.5) H5B(0.5)
 C6B(0.5) H6B(0.5) N2B(0.5) C7B(0.5) H7BA(0.5) H7BB(0.5) H7BC(0.5) O2B(0.5)
 C7C(0.5) H7CA(0.5) H7CB(0.5) N2C(0.5) C2C(0.5) H2C(0.5) C3C(0.5) C4C(0.5)
 H4C(0.5) C5C(0.5) H5C(0.5) C6C(0.5) H6C(0.5) O2C(0.5) C1S(0.5) H1SA(0.5)
 H1SB(0.5) H1SC(0.5) O1S(0.5) H1S(0.5)
 Fixed U11: C1S(0.063549)
 Fixed U33: C1S(0.20373)
5.a Riding coordinates:
 O1S(H1S), O2S(H2S)
5.b Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
5.c Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C31(H31A,H31B), C33(H33A,H33B), C35(H35A,H35B)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C16(H16), C23(H23), C2B(H2B), C4B(H4B), C5B(H5B), C6B(H6B),
 C2A(H2A), C4A(H4A), C5A(H5A), C6A(H6A), C2C(H2C), C4C(H4C), C5C(H5C), C6C(H6C)
5.e Fitted hexagon refined as free rotating group:
 C2B(C3B,C4B,C5B,C6B,N2B), N2C(C2C,C3C,C4C,C5C,C6C)
5.f X=CH2 refined with riding coordinates:
 C7C(H7CA,H7CB)
5.g 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), C7B(H7BA,H7BB,H7BC), C7A(H7AA,H7AB,H7AC), C1S(H1SA,H1SB,H1SC),
 C2S(H2SA,H2SB,H2SC)
5.h Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O11(H11), O13(H13), O18(H18), O20(H20), O25(H25), O27(H27)
;
_shelx_res_checksum              14147
_olex2_submission_special_instructions 'No special instructions were received'