Synthesis of hydroxylated azacalix[1]arene[3]pyridines from hydrolysis of high valent arylcopper complexes and conversion to a double azacalix[1]arene[3]pyridine host molecule
Zhang, Qian; Wang, Mei-Xiang; Organic Chemistry Frontiers 4 (2017) 283–; doi:10.1039/C6QO00669H

data_1553597
_publ_section_title
;
 Synthesis of hydroxylated azacalix[1]arene[3]pyridines from hydrolysis of
 high valent arylcopper complexes and conversion to a double
 azacalix[1]arene[3]pyridine host molecule
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              283
_journal_paper_doi               10.1039/C6QO00669H
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C50 H48 N14 O2, C4 H12 N2'
_chemical_formula_sum            'C54 H60 N16 O2'
_chemical_formula_weight         965.18
_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_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-10-29 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                69.768(4)
_cell_angle_beta                 84.466(3)
_cell_angle_gamma                84.513(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6636(3)
_cell_length_b                   15.1098(6)
_cell_length_c                   18.1939(7)
_cell_measurement_reflns_used    6821
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.5130
_cell_measurement_theta_min      4.0400
_cell_volume                     2475.53(17)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.8388
_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    -66.00  45.00   1.00   15.55    --    9.97 -19.00 -30.00  111
  2  \w      5.00  50.00   1.00   15.55    --    9.97 -99.00-120.00   45
  3  \w    -17.00  29.00   1.00   15.55    --  -11.85 -99.00 -60.00   46
  4  \w      2.00  77.00   1.00   15.55    --    9.97  38.00 150.00   75
  5  \w    -78.00 -41.00   1.00   15.55    --  -11.85 -38.00 -90.00   37
;
_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      -0.0360364000
_diffrn_orient_matrix_UB_12      -0.0373857000
_diffrn_orient_matrix_UB_13      0.0278874000
_diffrn_orient_matrix_UB_21      -0.0153698000
_diffrn_orient_matrix_UB_22      0.0277323000
_diffrn_orient_matrix_UB_23      0.0246071000
_diffrn_orient_matrix_UB_31      -0.0626694000
_diffrn_orient_matrix_UB_32      0.0186386000
_diffrn_orient_matrix_UB_33      -0.0187382000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21677
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         29.45
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85030
_exptl_absorpt_correction_type   none
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2948
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024.3626
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.5295
_refine_diff_density_min         -0.7522
_refine_diff_density_rms         0.0828
_refine_ls_d_res_high            0.7228
_refine_ls_d_res_low             6.2187
_refine_ls_goodness_of_fit_ref   1.0409
_refine_ls_matrix_type           full
_refine_ls_number_constraints    97
_refine_ls_number_parameters     665
_refine_ls_number_reflns         11520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0409
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+1.4806P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1452
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              20
_reflns_limit_k_min              -18
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                8295
_reflns_number_total             11520
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6qo00669h2.cif
_cod_data_source_block           20160801C4
_cod_original_cell_volume        2475.53(18)
_cod_database_code               1553597
_chemical_oxdiff_formula         C54H60O2N9
_reflns_odcompleteness_completeness 99.75
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N72(H72A,H72B)
2.b Secondary CH2 refined with riding coordinates:
 C68(H68A,H68B), C69(H69A,H69B), C70(H70A,H70B), C71(H71A,H71B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C48(H48), C46(H46), C37(H37), C38(H38), C36(H36), C6(H6),
 C50(H50), C51(H51), C4(H4), C5(H5), C21(H21), C52(H52), C27(H27), C22(H22),
 C25(H25), C26(H26), C23(H23), C53(H53), C55(H55), C54(H54)
2.d Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C58(H58A,H58B,H58C), C63(H63A,H63B,H63C), C61(H61A,H61B,
 H61C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C59(H59A,H59B,H59C), C60(H60A,
 H60B,H60C)
2.e Idealised tetrahedral OH refined as rotating group:
 O62(H62), O57(H57)
;
_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 1.407
_oxdiff_exptl_absorpt_empirical_full_min 0.723