Full Control of the Regiospecific N-Functionalization of C-Functionalized Cyclam Bisaminal Derivatives and Application to the Synthesis of their TETA, TE2A, and CB-TE2A Analogues.
Camus, Nathalie; Halime, Zakaria; Le Bris, Nathalie; Bernard, Hélène; Platas-Iglesias, Carlos; Tripier, Raphaël; The Journal of organic chemistry 79 (2014) 1885–1899; doi:10.1021/jo4028566

data_4029147
_publ_section_title
;
 Full Control of the Regiospecific N-Functionalization of C-Functionalized
 Cyclam Bisaminal Derivatives and Application to the Synthesis of their
 TETA, TE2A, and CB-TE2A Analogues.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1885
_journal_page_last               1899
_journal_paper_doi               10.1021/jo4028566
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C26 H38 N4 O Cu 2+, (Cl O4 1-)2'
_chemical_formula_sum            'C26 H38 Cl2 Cu N4 O9'
_chemical_formula_weight         685.04
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2010-07-09T19:07:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                77.317(15)
_cell_angle_beta                 82.748(14)
_cell_angle_gamma                89.651(14)
_cell_formula_units_Z            4
_cell_length_a                   8.9495(16)
_cell_length_b                   13.606(2)
_cell_length_c                   25.842(5)
_cell_measurement_reflns_used    1504
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      17.85
_cell_measurement_theta_min      2.6
_cell_volume                     3044.6(9)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 1980-2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3622
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Kappa-geometry diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method
;
4 stepped omega-scans over 115 deg. with kappa -79 deg. (chi -58.3 deg.),
phi 0, 90, 180, 270 deg.
sep 1 deg., exposure time 60 s
detector distance 50 mm
detector angle 30 deg.
;
_diffrn_orient_matrix_UB_11      -0.0201410303
_diffrn_orient_matrix_UB_12      -0.0494748978
_diffrn_orient_matrix_UB_13      0.0148142336
_diffrn_orient_matrix_UB_21      0.0710771015
_diffrn_orient_matrix_UB_22      -0.0041965266
_diffrn_orient_matrix_UB_23      0.0096305007
_diffrn_orient_matrix_UB_31      -0.0304755232
_diffrn_orient_matrix_UB_32      0.0197792153
_diffrn_orient_matrix_UB_33      0.0221928733
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1624
_diffrn_reflns_av_unetI/netI     0.4464
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21667
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.95
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'planar chip'
_exptl_crystal_F_000             1428
_exptl_crystal_recrystallization_method
'Slow evaporation of saturated solution'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         11071
_refine_ls_number_restraints     581
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.3102
_refine_ls_R_factor_gt           0.0886
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0290P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.2101
_reflns_number_gt                2609
_reflns_number_total             11071
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4028566_si_002.cif
_cod_data_source_block           cd41b-b0
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               4029147