The synthesis of unsymmetrically N-substituted chiral 1,4,7-triazacyclononanesElectronic supplementary information (ESI) available: Molecular modelling methodology. Figs. S1?S4: Lowest energy conformation calculated for the protonated form of 6b, 6b�HOAc, the protonated form of 6a and 6a�HOAc. Figs. S5 and S6: Charge distribution calculated for the protonated forms of 6a and 6b. See http://www.rsc.org/suppdata/ob/b4/b409259g/
Scheuermann, J. Erik W.; Sibbons, Kevin F.; Benoit, David M.; Motevalli, Majid; Watkinson, Michael; Organic & Biomolecular Chemistry 2 (2004) 2664–2670; doi:10.1039/b409259g

data_7153537
_publ_section_title
;
 The synthesis of unsymmetrically N-substituted chiral
 1,4,7-triazacyclononanesElectronic supplementary information (ESI)
 available: Molecular modelling methodology. Figs. S1?S4: Lowest energy
 conformation calculated for the protonated form of 6b, 6b&#xFFFD;HOAc,
 the protonated form of 6a and 6a&#xFFFD;HOAc. Figs. S5 and S6: Charge
 distribution calculated for the protonated forms of 6a and 6b. See
 http://www.rsc.org/suppdata/ob/b4/b409259g/
;
_journal_issue                   18
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              2664
_journal_page_last               2670
_journal_paper_doi               10.1039/b409259g
_journal_volume                  2
_journal_year                    2004
_chemical_formula_sum            'C24 H37 N3 O4 S2'
_chemical_formula_weight         495.69
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.752(4)
_cell_length_b                   11.183(5)
_cell_length_c                   21.829(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      11.98
_cell_measurement_theta_min      9.55
_cell_volume                     2624.7(19)
_computing_cell_refinement       'CAD4 /PC (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 /PC (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0053
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2679
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.8909
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   3
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.

;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.335
_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   -0.04(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+1.4596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                1875
_reflns_number_total             2622
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b409259gsup1.cif
_cod_data_source_block           4ks-23
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2624.6(19)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7153537