Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective Complexation with Ammonium Salts.
Zhang, Yu-Fei; Cao, Xiao-Ping; Chow, Hak-Fun; Kuck, Dietmar; The Journal of organic chemistry 82 (2017) 179–187; doi:10.1021/acs.joc.6b02326

data_4032244
_publ_section_title
;
 Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective
 Complexation with Ammonium Salts.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              179
_journal_page_last               187
_journal_paper_doi               10.1021/acs.joc.6b02326
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C38 H46 O7'
_chemical_formula_sum            'C38 H46 O7'
_chemical_formula_weight         614.75
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-29
_audit_creation_method
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Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
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_cell_angle_alpha                85.280(5)
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_cell_angle_gamma                87.723(4)
_cell_formula_units_Z            2
_cell_length_a                   11.2358(6)
_cell_length_b                   11.5376(6)
_cell_length_c                   12.5681(9)
_cell_measurement_reflns_used    2913
_cell_measurement_temperature    294.44(10)
_cell_measurement_theta_max      27.7720
_cell_measurement_theta_min      3.7310
_cell_volume                     1622.44(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.44(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -3.00   24.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000  -30.0000 27

  2 omega   -7.00   23.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000 -150.0000 30

  3 omega   14.00   68.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000  150.0000 54

  4 omega   38.00   65.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000  -30.0000 27

  5 omega  -46.00   49.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -77.0000  -30.0000 95

  6 omega   23.00   89.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000 -150.0000 66

  7 omega  -49.00   32.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -57.0000   60.0000 81
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0209895000
_diffrn_orient_matrix_UB_12      -0.0553975000
_diffrn_orient_matrix_UB_13      0.0224672000
_diffrn_orient_matrix_UB_21      -0.0018655000
_diffrn_orient_matrix_UB_22      -0.0218558000
_diffrn_orient_matrix_UB_23      -0.0510620000
_diffrn_orient_matrix_UB_31      0.0595610000
_diffrn_orient_matrix_UB_32      0.0162638000
_diffrn_orient_matrix_UB_33      -0.0097338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11512
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.55
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.551
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6380
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0792
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1012P)^2^+1.7081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2094
_refine_ls_wR_factor_ref         0.2369
_reflns_number_gt                4367
_reflns_number_total             6380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02326_si_002.cif
_cod_data_source_block           tbtq_1027
_cod_database_code               4032244
_reflns_odcompleteness_completeness 99.77
_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. Uiso/Uaniso restraints and constraints
Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,
 H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B),
 C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C26(H26)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'