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_7153536
_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            'C28 H41 N3 O5 S2'
_chemical_formula_weight         563.76
_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                   7.47600(10)
_cell_length_b                   14.3100(2)
_cell_length_c                   26.3880(4)
_cell_measurement_temperature    120(2)
_cell_volume                     2823.03(7)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
;
DENZO (Otwinowski and Minor, 1997
COLLECT (Hooft, 1998)
;
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. (1997) J. Appl. Cryst. 30, 565.'
_computing_publication_material
'WINGX, Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF-99(P.T. Beurskens, 1999)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 7.77
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  ' Enraf Nonius KappaCCd area detector'
_diffrn_measurement_method       'phi and Omega scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius fr591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0641
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25309
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.99949
_exptl_absorpt_correction_T_min  0.94514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Using multiple and symmetry-related data measurements via the program
SORTAV
See R.H. Blessing, Acta Crysta (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_coef       0.0042(6)
_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   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.5189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                5198
_reflns_number_total             6397
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b409259gsup1.cif
_cod_data_source_block           valacmc2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

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_sg_symbol_H-M      P212121
_cod_database_code               7153536