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_4029148
_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 Br Cu N4 O +, Cl O4 -, 0.5(H2 O)'
_chemical_formula_sum            'C26 H39 Br Cl Cu N4 O5.5'
_chemical_formula_weight         674.51
_chemical_name_systematic
;
 ?
;
_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_creation_date             2011-07-08T19:50:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                92.710(7)
_cell_angle_beta                 94.643(8)
_cell_angle_gamma                110.551(9)
_cell_formula_units_Z            4
_cell_length_a                   13.3503(14)
_cell_length_b                   14.8457(14)
_cell_length_c                   15.8604(14)
_cell_measurement_reflns_used    1914
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      31.6655
_cell_measurement_theta_min      2.9035
_cell_volume                     2924.1(5)
_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, 2008)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa-geometry diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0354141224
_diffrn_orient_matrix_UB_12      -0.0199380093
_diffrn_orient_matrix_UB_13      0.030906103
_diffrn_orient_matrix_UB_21      0.036010255
_diffrn_orient_matrix_UB_22      -0.0216349086
_diffrn_orient_matrix_UB_23      0.0171554742
_diffrn_orient_matrix_UB_31      0.0265893621
_diffrn_orient_matrix_UB_32      0.041922852
_diffrn_orient_matrix_UB_33      0.0279409303
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_unetI/netI     0.2126
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13515
_diffrn_reflns_theta_full        20.82
_diffrn_reflns_theta_max         20.82
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.249
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.849
_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            blue
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
        planar, main faces {-1 1 0}
;
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.982
_refine_diff_density_min         -0.992
_refine_diff_density_rms         0.14
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     661
_refine_ls_number_reflns         6109
_refine_ls_number_restraints     896
_refine_ls_restrained_S_all      0.857
_refine_ls_R_factor_all          0.1745
_refine_ls_R_factor_gt           0.0853
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1382P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2167
_refine_ls_wR_factor_ref         0.248
_reflns_number_gt                2667
_reflns_number_total             6109
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo4028566_si_002.cif
_cod_data_source_block           cd41bis-b0
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C52 H78 Br2 Cl2 Cu2 N8 O11'
_cod_original_formula_weight         1349.02
_cod_original_formula_moiety
;
        2(C26 H38 Br Cu N4 O +), 2(Cl O4 -), H2 O
;
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029148