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_4029144
_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_absolute_configuration ad
_chemical_formula_moiety         'C21 H31 N4 O2 1+, Br 1-, 3(H2 O)'
_chemical_formula_sum            'C21 H37 Br N4 O5'
_chemical_formula_weight         505.46
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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             2010-10-07T09:17:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.925(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9358(19)
_cell_length_b                   8.2953(6)
_cell_length_c                   14.5790(14)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      23.84
_cell_measurement_theta_min      2.7
_cell_volume                     2306.6(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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.
step 1 deg., exposure time 60 s
detector distance 50 mm
detector angle 30 deg.
;
_diffrn_orient_matrix_UB_11      -0.0039571123
_diffrn_orient_matrix_UB_12      0.0849601115
_diffrn_orient_matrix_UB_13      -0.0029991325
_diffrn_orient_matrix_UB_21      -0.036925995
_diffrn_orient_matrix_UB_22      -0.0092101098
_diffrn_orient_matrix_UB_23      -0.0175560731
_diffrn_orient_matrix_UB_31      -0.0022579742
_diffrn_orient_matrix_UB_32      0.0020090512
_diffrn_orient_matrix_UB_33      0.0476419142
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8530
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.73
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
        fragment of flat needle, axis [0 0 1], main faces {1 0 0}
;
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3295
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0305P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                2518
_reflns_number_total             3295
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4028566_si_002.cif
_cod_data_source_block           cd46-b0
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4029144