The synthesis of 1,2-bis(1,5,9-triazacyclododecyl)ethane: a showcase for the importance of the linker length within bis(alkylating) reagents.
Medina-Molner, Alfredo; Blacque, Olivier; Spingler, Bernhard; Organic letters 9 (2007) 4829–4831; doi:10.1021/ol7021627

data_1505592
_publ_section_title
;
 The synthesis of 1,2-bis(1,5,9-triazacyclododecyl)ethane: a showcase for
 the importance of the linker length within bis(alkylating) reagents.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              4829
_journal_page_last               4831
_journal_paper_doi               10.1021/ol7021627
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C26 H52 F12 N6 O13 S4'
_chemical_formula_weight         1012.98
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                67.366(14)
_cell_angle_beta                 86.690(15)
_cell_angle_gamma                70.747(14)
_cell_formula_units_Z            2
_cell_length_a                   10.9082(19)
_cell_length_b                   15.094(3)
_cell_length_c                   15.126(3)
_cell_measurement_reflns_used    21925
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      123.67
_cell_measurement_theta_min      6.34
_cell_volume                     2163.3(8)
_computing_cell_refinement       'X-Area (Stoe, 2005)'
_computing_data_collection       'X-Area (Stoe, 2005)'
_computing_data_reduction        'X-RED32 (Stoe, 2005)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       '/o oscillation scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5236
_diffrn_reflns_theta_full        55.00
_diffrn_reflns_theta_max         55.00
_diffrn_reflns_theta_min         3.18
_diffrn_standards_interval_count 'every image'
_diffrn_standards_interval_time  18
_diffrn_standards_number         50-200
_exptl_absorpt_coefficient_mu    3.071
_exptl_absorpt_correction_T_max  0.7295
_exptl_absorpt_correction_T_min  0.4000
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1052
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.0034(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         5236
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0920
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1575P)^2^+6.1378P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2617
_refine_ls_wR_factor_ref         0.2896
_reflns_number_gt                3096
_reflns_number_total             5236
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7021627-file005.cif
_cod_data_source_block           am050207
_cod_original_cell_volume        2163.2(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505592