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_1553595
_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, 2(H2 O)'
_chemical_formula_sum            'C50 H52 N14 O4'
_chemical_formula_weight         913.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-10-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-29 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.32(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.842(2)
_cell_length_b                   21.609(4)
_cell_length_c                   25.234(5)
_cell_measurement_reflns_used    15663
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4825
_cell_measurement_theta_min      1.2408
_cell_volume                     5365.2(18)
_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  'Olex2 (Dolomanov et al., 2009)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.0297
	          2theta: -20.0699
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0297
	          2theta: -20.0699
;
_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      0.0377
_diffrn_orient_matrix_UB_12      -0.0183
_diffrn_orient_matrix_UB_13      -0.0926
_diffrn_orient_matrix_UB_21      0.0151
_diffrn_orient_matrix_UB_22      0.0437
_diffrn_orient_matrix_UB_23      -0.0025
_diffrn_orient_matrix_UB_31      0.0348
_diffrn_orient_matrix_UB_32      -0.0111
_diffrn_orient_matrix_UB_33      0.0154
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            37182
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.199
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_min         1.614
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_description       rod
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         9650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0942
_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^)+(0.0670P)^2^+4.8984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8156
_reflns_number_total             9650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00669h2.cif
_cod_data_source_block           mx4093_sq
_cod_original_cell_volume        5365.0(19)
_cod_database_code               1553595
_diffrn_number_total             12615
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B), O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C6(H6), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17),
 C21(H21), C22(H22), C23(H23), C27(H27), C31(H31), C34(H34), C35(H35), C36(H36),
  C40(H40), C41(H41), C42(H42), C46(H46), C47(H47), C48(H48)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C25(H25A,H25B,
 H25C), C32(H32A,H32B,H32C), C38(H38A,H38B,H38C), C44(H44A,H44B,H44C), C50(H50A,
 H50B,H50C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_fab_checksum              22679
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'