1,4,7-Triazacyclononane Ligands Bearing Tertiary Alkyl Nitrogen Substituents
Arumugam Thangavel; Marika Wieliczko; John Bacsa; Christopher C. Scarborough; Inorganic Chemistry 52 (2013) 13282–13287; doi:10.1021/ic402626p

data_4336786
_publ_contact_author_address
; 
Department of Chemistry
Emory University
Atlanta, GA 30322, USA
;
_publ_contact_author_email       scarborough@emory.edu
_publ_contact_author_name        'Scarborough, Christopher C.'
_publ_section_title
;
 1,4,7-Triazacyclononane Ligands Bearing Tertiary Alkyl Nitrogen
 Substituents
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              13282
_journal_page_last               13287
_journal_paper_doi               10.1021/ic402626p
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C18 H39 Cl Mn N3, C H2 Cl2, C24 H20 B'
_chemical_formula_sum            'C43 H61 B Cl3 Mn N3'
_chemical_formula_weight         792.04
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-06-10
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.705(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0646(18)
_cell_length_b                   16.376(2)
_cell_length_c                   18.303(2)
_cell_measurement_reflns_used    6806
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.627
_cell_measurement_theta_min      2.200
_cell_volume                     4215.3(9)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 v2011.2-4 (Bruker, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.839
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.839
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34294
_diffrn_reflns_point_group_measured_fraction_full 0.839
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         23.715
_diffrn_reflns_theta_min         1.448
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.5970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0790 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.8013.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       prism
_exptl_crystal_F_000             1684
_exptl_crystal_size_max          0.553
_exptl_crystal_size_mid          0.294
_exptl_crystal_size_min          0.274
_refine_diff_density_max         0.941
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         6387
_refine_ls_number_restraints     166
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0941P)^2^+4.6129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4902
_reflns_number_total             6387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic402626p_si_002_05.cif
_cod_data_source_block           attacnmnclbph4
_cod_database_code               4336786
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C7A \\sim N1-C7B
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C7A \\sim C7B \\sim C10B \\sim C10A \\sim C9B \\sim C9A \\sim C8B \\sim C8A: 
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Same fragment restrains
{C7B, C8B, C9B, C10B}
as
{C7A, C8A, C9A, C10A}
5. others
 Sof(C7B)=Sof(C8B)=Sof(H8BA)=Sof(H8BB)=Sof(H8BC)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=
 Sof(H9BC)=Sof(C10B)=Sof(H10A)=Sof(H10B)=Sof(H10C)=1-FVAR(1)
 Sof(C7A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=
 Sof(H9AC)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C4(H4A,H4B), C1(H1A,H1B), C6(H6A,H6B), C3(H3A,H3B),
 C1S(H1SA,H1SB)
6.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C30(H30), C21(H21), C22(H22), C36(H36), C23(H23), C42(H42),
 C24(H24), C32(H32), C29(H29), C38(H38), C41(H41), C35(H35), C33(H33), C26(H26),
  C34(H34), C40(H40), C28(H28), C27(H27), C39(H39)
6.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C18(H18A,H18B,
 H18C), C17(H17A,H17B,H17C), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,H9BC),
 C10B(H10A,H10B,H10C), C13(H13A,H13B,H13C), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,
 H9AC), C10A(H10D,H10E,H10F)
;
_shelxl_version_number           2013-4