Synthesis and Structure of Functionalized Homo Heteracalix[2]arene[2]triazines: Effect of All Heteroatom Bridges on Macrocyclic Conformation.
Liang, Dong-Dong; Wang, Mei-Xiang; The Journal of organic chemistry 83 (2018) 3316–3324; doi:10.1021/acs.joc.8b00284

data_4033534
_publ_section_title
;
 Synthesis and Structure of Functionalized Homo
 Heteracalix[2]arene[2]triazines: Effect of All Heteroatom Bridges on
 Macrocyclic Conformation.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3316
_journal_page_last               3324
_journal_paper_doi               10.1021/acs.joc.8b00284
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C36 H50 N14 O4'
_chemical_formula_sum            'C36 H50 N14 O4'
_chemical_formula_weight         742.90
_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
_audit_creation_date             2017-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.877(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3134(4)
_cell_length_b                   17.4067(5)
_cell_length_c                   21.6601(7)
_cell_measurement_reflns_used    9590
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.2700
_cell_measurement_theta_min      2.0670
_cell_volume                     4465.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18132
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.080
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.96914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.064
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_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         10086
_refine_ls_number_restraints     125
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+1.3786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6685
_reflns_number_total             10086
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00284_si_009.cif
_cod_data_source_block           mx5936c
_cod_depositor_comments
'Adding full bibliography for 4033534--4033537.cif.'
_cod_original_cell_volume        4465.4(2)
_cod_database_code               4033534
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N11-C13 = N11-C13A
 1.47 with sigma of 0.01
 C14A-C13A = C14-C13
 1.53 with sigma of 0.01
 C16-C15
 1.53 with sigma of 0.01
 C25-C24 = C25A-C24 = C27-C24 = C27A-C24 = C26-C24 = C26A-C24
 1.53 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C25 \\sim C25A \\sim C27 \\sim C27A \\sim C26 \\sim C26A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
C13 \\sim C13A \\sim C14 \\sim C14A: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04
Uanis(C25) \\sim Ueq, Uanis(C25A) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C27A)
\\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C26A) \\sim Ueq: with sigma of 0.001 and
sigma for terminal atoms of 0.002
Uanis(C13) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C14A)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=
 Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=
 Sof(H25F)=Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=1-FVAR(1)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C25)=
 Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27)=
 Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C33(H33A,H33B), C35(H35A,H35B), C13A(H13C,H13D)
5.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N7(H7), N12(H12), N14(H14), C5(H5A), C7(H7A), C8(H8), C9(H9),
 C18(H18), C20(H20), C21(H21), C22(H22)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C14A(H14D,H14E,H14F),
 C26A(H26D,H26E,H26F), C25A(H25D,H25E,H25F), C27A(H27D,H27E,H27F)
;
_shelx_res_checksum              51765
_shelx_hkl_checksum              49648
_shelx_fab_checksum              66265
_olex2_submission_special_instructions 'No special instructions were received'