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_4035163
_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 H29 N11 O6, C4 H8 O0.5, 0.5(O)'
_chemical_formula_sum            'C30 H37 N11 O7'
_chemical_formula_weight         663.70
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.690(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1376(5)
_cell_length_b                   12.3877(5)
_cell_length_c                   18.7603(7)
_cell_measurement_reflns_used    4203
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.5820
_cell_measurement_theta_min      4.0220
_cell_volume                     3274.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     51.00  81.00   1.00    1.00    --   40.81 -99.00  30.00   30
  2  \w     72.00 137.00   1.00   10.00    --  111.58 -45.00  60.00   65
  3  \w    121.00 159.00   1.00   10.00    --  111.58  30.00  90.00   38
  4  \w    138.00 173.00   1.00   10.00    --  111.58  45.00   0.00   35
  5  \w    139.00 169.00   1.00   10.00    --  111.58 125.00 120.00   30
  6  \w     91.00 130.00   1.00   10.00    --  111.58  45.00   0.00   39
  7  \w     86.00 112.00   1.00   10.00    --  111.58  30.00  90.00   26
  8  \w     41.00 100.00   1.00   10.00    --  111.58 -45.00  30.00   59
  9  \w      8.00  58.00   1.00    1.00    --   40.81 -99.00-150.00   50
 10  \w     35.00 138.00   1.00   10.00    --  111.58 -30.00-180.00  103
 11  \w    111.00 159.00   1.00   10.00    --  111.58  77.00-150.00   48
 12  \w    -90.00  -9.00   1.00    1.00    --  -40.81 125.00-120.00   81
 13  \w   -113.00 -14.00   1.00    1.00    --  -40.81 -57.00   0.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1087908000
_diffrn_orient_matrix_UB_12      -0.0084446000
_diffrn_orient_matrix_UB_13      -0.0128298000
_diffrn_orient_matrix_UB_21      0.0109888000
_diffrn_orient_matrix_UB_22      -0.0740683000
_diffrn_orient_matrix_UB_23      -0.0647760000
_diffrn_orient_matrix_UB_31      0.0010787000
_diffrn_orient_matrix_UB_32      -0.0995557000
_diffrn_orient_matrix_UB_33      0.0492466000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13214
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.922
_diffrn_reflns_theta_min         3.771
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       rod
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         6695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0655
_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^)+(0.0880P)^2^+1.7020P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.1948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5040
_reflns_number_total             6695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00284_si_007.cif
_cod_data_source_block           exp_1193
_cod_database_code               4035163
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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. Others
 Fixed Sof: O7(0.5) O8(0.5)
3.a Riding coordinates:
 N6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C17(H17A,H17B), C18(H18A,H18B),
 C19(H19A,H19B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5), N7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C24(H24),
 C25(H25), C26(H26)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              15720
_shelx_hkl_checksum              20707
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.882
_oxdiff_exptl_absorpt_empirical_full_min 0.514