Synthesis of a novel water-soluble cylindrical macrotricyclic host and its complexation with N-methylquinolinium and N-methylisoquinolinium salts: formation of 1 : 2 complexes in water.
Zeng, Fei; Chen, Chuan-Feng; Organic & biomolecular chemistry 13 (2015) 1988–1991; doi:10.1039/c4ob02533d

data_7154261
_publ_section_title
;
 Synthesis of a novel water-soluble cylindrical macrotricyclic host and
 its complexation with N-methylquinolinium and N-methylisoquinolinium
 salts: formation of 1&#x2009;:&#x2009;2 complexes in water.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1988
_journal_page_last               1991
_journal_paper_doi               10.1039/c4ob02533d
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C64 H70 O24, 2(C10 H10 N)'
_chemical_formula_sum            'C84 H90 N2 O24'
_chemical_formula_weight         1511.57
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-04-25 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.603(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.814(4)
_cell_length_b                   14.779(3)
_cell_length_c                   21.657(5)
_cell_measurement_reflns_used    13890
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4851
_cell_measurement_theta_min      1.3779
_cell_volume                     5028(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
'XS (Sheldrick, 2008)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0352
_diffrn_orient_matrix_UB_12      -0.0027
_diffrn_orient_matrix_UB_13      0.0530
_diffrn_orient_matrix_UB_21      0.0218
_diffrn_orient_matrix_UB_22      0.0631
_diffrn_orient_matrix_UB_23      -0.0113
_diffrn_orient_matrix_UB_31      -0.0325
_diffrn_orient_matrix_UB_32      0.0164
_diffrn_orient_matrix_UB_33      0.0289
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            40163
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         1.672
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.998
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.069
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.622
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         11480
_refine_ls_number_restraints     402
_refine_ls_restrained_S_all      1.616
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.1131
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2870
_refine_ls_wR_factor_ref         0.3004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7634
_reflns_number_total             11480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob02533d2.cif
_cod_data_source_block           sa3174
_cod_depositor_comments          'Adding full bibliography for 7154261.cif.'
_cod_original_cell_volume        5027.9(19)
_cod_database_code               7154261
_shelxl_version_number           2013-4
_diffrn_number_total             11938
_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 C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 C39A-C38A = C38A-C37 = C35A-C34A = C36A-C35A = C37-C36A = C42A-C37 = C42A-
 C41A = C41A-C40A = C40A-C39A
 1.39 with sigma of 0.01
 N1A-C34A = N1A-C38A
 1.34 with sigma of 0.01
 N1A-C33
 1.47 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim
C40 \\sim C41 \\sim C42 \\sim N1A \\sim C35A \\sim C36A \\sim C34A \\sim C38A
\\sim C39A \\sim C40A \\sim C41A \\sim C42A: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04
Uanis(N1) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35)
\\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq,
Uanis(C39) \\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42)
\\sim Ueq, Uanis(N1A) \\sim Ueq, Uanis(C35A) \\sim Ueq, Uanis(C36A) \\sim Ueq,
Uanis(C34A) \\sim Ueq, Uanis(C38A) \\sim Ueq, Uanis(C39A) \\sim Ueq,
Uanis(C40A) \\sim Ueq, Uanis(C41A) \\sim Ueq, Uanis(C42A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H33D)=Sof(H33E)=Sof(H33F)=Sof(N1A)=Sof(C35A)=Sof(H35A)=Sof(C36A)=
 Sof(H36A)=Sof(C34A)=Sof(H34A)=Sof(C38A)=Sof(C39A)=Sof(H39A)=Sof(C40A)=
 Sof(H40A)=Sof(C41A)=Sof(H41A)=Sof(C42A)=Sof(H42A)=1-FVAR(1)
 Sof(N1)=Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=
 Sof(C36)=Sof(H36)=Sof(C38)=Sof(C39)=Sof(H39)=Sof(C40)=Sof(H40)=Sof(C41)=
 Sof(H41)=Sof(C42)=Sof(H42)=FVAR(1)
5.a Riding coordinates:
 O2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,
 H21B), C22(H22A,H22B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B),
 C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B)
5.c Me refined with riding coordinates:
 C33(H33A,H33B,H33C), C33(H33D,H33E,H33F)
5.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C24(H24), C26(H26), C34(H34), C35(H35), C36(H36),
 C39(H39), C40(H40), C41(H41), C42(H42), C35A(H35A), C36A(H36A), C34A(H34A),
 C39A(H39A), C40A(H40A), C41A(H41A), C42A(H42A)
5.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              49318