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_4032245
_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         'C25 H26 O4'
_chemical_formula_sum            'C25 H26 O4'
_chemical_formula_weight         390.46
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-28
_audit_creation_method
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Olex2 1.2
(compiled 2014.11.25 svn.r3098 for OlexSys, GUI svn.r4951)
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_cell_angle_alpha                90.00
_cell_angle_beta                 105.687(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7954(6)
_cell_length_b                   10.4000(6)
_cell_length_c                   16.4115(8)
_cell_measurement_reflns_used    1481
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.0750
_cell_measurement_theta_min      3.9140
_cell_volume                     2102.6(2)
_computing_cell_refinement
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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_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
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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_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      293(2)
_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   46.00   96.40   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946 -178.0000  -60.0000 42

  2 omega  -48.00   24.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -57.0000  -90.0000 60

  3 omega  -46.00   20.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -77.0000  150.0000 55

  4 omega  -39.00   27.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -38.0000    0.0000 55
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0049466000
_diffrn_orient_matrix_UB_12      -0.0326592000
_diffrn_orient_matrix_UB_13      -0.0388219000
_diffrn_orient_matrix_UB_21      0.0337821000
_diffrn_orient_matrix_UB_22      -0.0498935000
_diffrn_orient_matrix_UB_23      0.0220049000
_diffrn_orient_matrix_UB_31      -0.0464039000
_diffrn_orient_matrix_UB_32      -0.0330018000
_diffrn_orient_matrix_UB_33      0.0050384000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9563
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.30
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98626
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0092(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.3814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1505
_reflns_number_gt                2246
_reflns_number_total             4121
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02326_si_003.cif
_cod_data_source_block           zhangyf141117
_cod_original_cell_volume        2102.57(19)
_cod_database_code               4032245
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C9(H9), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'