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_1553596
_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 H46 N14 O2, 0.59(C H Cl3), 1.41(C3 H11 N2)'
_chemical_formula_sum            'C54.83 H62.12 Cl1.76 N16.83 O2'
_chemical_formula_weight         1051.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-17
_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                90
_cell_angle_beta                 90.70(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.402(6)
_cell_length_b                   9.816(2)
_cell_length_c                   18.722(4)
_cell_measurement_reflns_used    8277
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4814
_cell_measurement_theta_min      1.4341
_cell_volume                     5219.2(19)
_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 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0044
	          2theta: -20.0947
scan:
	Number of images: 270
	           Slice: -76.2500 - 58.7500
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0044
	          2theta: -20.0947
;
_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      0.0085
_diffrn_orient_matrix_UB_12      -0.0315
_diffrn_orient_matrix_UB_13      -0.0133
_diffrn_orient_matrix_UB_21      0.0986
_diffrn_orient_matrix_UB_22      0.0200
_diffrn_orient_matrix_UB_23      0.0160
_diffrn_orient_matrix_UB_31      -0.0034
_diffrn_orient_matrix_UB_32      -0.0222
_diffrn_orient_matrix_UB_33      0.0485
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18221
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.434
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             2219
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.112
_refine_diff_density_max         1.921
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0805
_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^)+(0.1200P)^2^+9.5996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2196
_refine_ls_wR_factor_ref         0.2259
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5417
_reflns_number_total             5976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00669h2.cif
_cod_data_source_block           mx5075
_cod_original_cell_volume        5219.2(18)
_cod_database_code               1553596
_diffrn_number_total             6334
_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, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(N8)=Sof(H8D)=Sof(H8E)=Sof(H8F)=Sof(N9)=Sof(H9A)=Sof(H9B)=Sof(C26)=
 Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C29)=Sof(H29)=FVAR(1)
3.a Rotating group:
 N9(H9A,H9B)
3.b Ternary CH refined with riding coordinates:
 C29(H29)
3.c Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B)
3.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18),
 C22(H22), C23(H23), C24(H24)
3.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C20(H20A,H20B,H20C),
 N8(H8D,H8E,H8F)
;
_shelx_res_checksum              75279
_shelx_hkl_checksum              75780
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'