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_1505591
_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            'C14 H23 F6 N3 O6 S2'
_chemical_formula_weight         507.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.149(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.4218(8)
_cell_length_b                   12.2877(4)
_cell_length_c                   23.2598(11)
_cell_measurement_reflns_used    7997
_cell_measurement_temperature    183(2)
_cell_volume                     4188.4(4)
_computing_cell_refinement       'IPDS (Stoe, 1999)'
_computing_data_collection       'IPDS (Stoe, 1999)'
_computing_data_reduction        'X-RED (Stoe, 1999)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       '/f oscillation scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            89654
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         2.68
_diffrn_standards_interval_count 'every image'
_diffrn_standards_interval_time  18
_diffrn_standards_number         50-200
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         12688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1239P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1792
_refine_ls_wR_factor_ref         0.1917
_reflns_number_gt                8973
_reflns_number_total             12688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7021627-file004.cif
_cod_data_source_block           am150305
_cod_original_cell_volume        4188.4(3)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1505591