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_1505590
_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            'C24 H50 F12 N6 O12 S4'
_chemical_formula_weight         970.94
_chemical_name_systematic
; 
 ? 
;
_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                 98.892(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.130(2)
_cell_length_b                   14.1193(13)
_cell_length_c                   20.129(3)
_cell_measurement_reflns_used    10908
_cell_measurement_temperature    183(2)
_cell_volume                     4248.4(9)
_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 0.937
_diffrn_measured_fraction_theta_max 0.937
_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  0.1446
_diffrn_reflns_av_sigmaI/netI    0.1546
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12362
_diffrn_reflns_theta_full        54.99
_diffrn_reflns_theta_max         54.99
_diffrn_reflns_theta_min         3.41
_diffrn_standards_interval_count 'every image'
_diffrn_standards_interval_time  27
_diffrn_standards_number         50-200
_exptl_absorpt_coefficient_mu    3.082
_exptl_absorpt_correction_T_max  0.9095
_exptl_absorpt_correction_T_min  0.6827
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       0.0088(10)
_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   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         4989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.2178
_refine_ls_R_factor_gt           0.1283
_refine_ls_shift/su_max          0.095
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1918P)^2^+17.7943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3067
_refine_ls_wR_factor_ref         0.3789
_reflns_number_gt                2381
_reflns_number_total             4989
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7021627-file003.cif
_cod_data_source_block           am211005
_cod_original_cell_volume        4248.6(10)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1505590