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_4035160
_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         'C26 H30 N10 O4, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C26.5 H31 Cl N10 O4'
_chemical_formula_weight         589.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 89.996(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.626(3)
_cell_length_b                   14.735(4)
_cell_length_c                   20.914(6)
_cell_measurement_reflns_used    8738
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4842
_cell_measurement_theta_min      1.3820
_cell_volume                     2966.4(15)
_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  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 9.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0857
	          2theta: -19.8572
scan:
	Number of images: 270
	           Slice: -76.2500 - 58.7500
	     Image width: 0.5000
	        Exp time: 9.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0857
	          2theta: -19.8572
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0000
_diffrn_orient_matrix_UB_12      -0.0145
_diffrn_orient_matrix_UB_13      0.1029
_diffrn_orient_matrix_UB_21      0.0402
_diffrn_orient_matrix_UB_22      0.0541
_diffrn_orient_matrix_UB_23      0.0077
_diffrn_orient_matrix_UB_31      -0.0385
_diffrn_orient_matrix_UB_32      0.0281
_diffrn_orient_matrix_UB_33      0.0040
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18192
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.199
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_min         1.691
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 2407 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.41(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     808
_refine_ls_number_reflns         10384
_refine_ls_number_restraints     190
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0920
_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^)+(0.1134P)^2^+2.2696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2218
_refine_ls_wR_factor_ref         0.2404
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                8258
_reflns_number_total             10384
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00284_si_006.cif
_cod_data_source_block           a
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C53 H62 Cl2 N20 O8'
_cod_original_formula_weight         1178.12
_cod_original_formula_moiety         '2(C26 H30 N10 O4), C H2 Cl2'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        2966.5(14)
_cod_database_code               4035160
_diffrn_number_total             7071
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H4AA of N4A, H4 of N4, H6 of N6, H7 of N7, H7A of N7A,
  H6AA of N6A, H5A of N5A, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H5 of N5
2. Restrained distances
 C20-C19 = C21-C20 = C21-C22
 1.54 with sigma of 0.01
 C25A-C26A = C25A-C24A = C23A-C24A
 1.54 with sigma of 0.01
 C23A-C24B = C25B-C24B = C26B-C25B
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C20B \\sim C21B \\sim C22B: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
C24A \\sim C25A \\sim C26A \\sim C24B \\sim C25B \\sim C26B: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C20) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C20B)
\\sim Ueq, Uanis(C21B) \\sim Ueq, Uanis(C22B) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C24A) \\sim Ueq, Uanis(C26A) \\sim Ueq, Uanis(C25A) \\sim Ueq,
Uanis(C24B) \\sim Ueq, Uanis(C25B) \\sim Ueq, Uanis(C26B) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H23E)=Sof(H23F)=Sof(C24B)=Sof(H24E)=Sof(H24F)=Sof(C25B)=Sof(H25E)=
 Sof(H25F)=Sof(C26B)=Sof(H26G)=Sof(H26H)=Sof(H26I)=1-FVAR(1)
 Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24C)=Sof(H24D)=Sof(C25A)=Sof(H25C)=
 Sof(H25D)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=FVAR(1)
 Sof(H19C)=Sof(H19D)=Sof(C20B)=Sof(H20C)=Sof(H20D)=Sof(C21B)=Sof(H21C)=
 Sof(H21D)=Sof(C22B)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(2)
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(2)
5.a Riding coordinates:
 N5(H5), N5A(H5A), C26A(H26D,H26E,H26F), C26B(H26G,H26H,H26I)
5.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C19(H19C,H19D), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C20(H20A,H20B), C21(H21A,H21B), C20B(H20C,H20D), C21B(H21C,H21D),
 C19A(H19E,H19F), C20A(H20E,H20F), C21A(H21E,H21F), C23A(H23C,H23D), C23A(H23E,
 H23F), C24A(H24C,H24D), C25A(H25C,H25D), C24B(H24E,H24F), C25B(H25E,H25F),
 C27(H27A,H27B)
5.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N6(H6), N7(H7), C2(H2), C3(H3), C4(H4A), C6(H6A), C11(H11), C12(H12),
 C13(H13), C15(H15), N4A(H4AA), N6A(H6AA), N7A(H7A), C2A(H2A), C3A(H3A),
 C4A(H4AB), C6A(H6AB), C11A(H11A), C12A(H12A), C13A(H13A), C15A(H15A)
5.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C22(H22A,H22B,H22C), C22B(H22D,H22E,H22F), C22A(H22G,
 H22H,H22I)
;
_shelx_res_checksum              91999
_shelx_hkl_checksum              77710
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'