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_4336782
_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         '2(C18 H39 Cl Co N3), 2(F6 P)'
_chemical_formula_sum            'C36 H78 Cl2 Co2 F12.01 N6 P2'
_chemical_formula_weight         1073.98
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-06-11
_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
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.4379(15)
_cell_length_b                   17.5125(15)
_cell_length_c                   33.949(3)
_cell_measurement_reflns_used    9005
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.622
_cell_measurement_theta_min      2.326
_cell_volume                     9772.9(15)
_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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0561
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            60697
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         1.725
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  0.4322
_exptl_absorpt_correction_T_min  0.3280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0690 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.7589.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             4496
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.416
_exptl_crystal_size_min          0.324
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     904
_refine_ls_number_reflns         12113
_refine_ls_number_restraints     2175
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+7.1103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8705
_reflns_number_total             12113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic402626p_si_002_01.cif
_cod_data_source_block           at1120co
_cod_database_code               4336782
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 P1A-F5A = P1A-F3A = P1A-F6A = P1A-F4A = P1A-F1A = P1A-F2A = P2A-F7A = P2A-
 F12A = P2A-F10A = P2A-F11A = P2A-F8A = P2A-F9A
 1.582 with sigma of 0.01
 P1B-F2B = P1A-F5A = P1A-F3A = P1A-F6A = P1A-F4A = P1A-F1A = P1A-F2A = P1B-F4B
 = P1B-F3B = P1B-F1B = P1B-F5B = P1B-F6B = P2B-F7B = P2B-F11B = P2B-F8B = P2B-
 F10B = P2B-F12B = P2B-F9B = P2A-F7A = P2A-F12A = P2A-F10A = P2A-F11A = P2A-F8A
 = P2A-F9A
 1.582 with sigma of 0.01
 N4-C33B \\sim N4-C33A
 with sigma of 0.005
 F4C-F1C \\sim F4C-F2C \\sim F4C-F3C \\sim F5C-F4C \\sim F5C-F1C \\sim F5C-F2C 
\\sim F6C-F5C \\sim F3C-F1C
 \\sim F6C-F3C \\sim F3C-F2C \\sim F6C-F1C \\sim F6C-F2C
 with sigma of 0.005
 P1A-F4A \\sim P1A-F1A \\sim P1A-F2A \\sim P1A-F3A \\sim P1A-F5A \\sim P1A-F6A 
\\sim P2B-F7B \\sim P2B-F8B
 \\sim P2B-F9B \\sim P2B-F10B \\sim P2B-F11B \\sim P2B-F12B
 with sigma of 0.005
 F9B-F11B \\sim F11B-F10B \\sim F7B-F11B \\sim F8B-F11B \\sim F7B-F12B 
\\sim F7B-F10B \\sim F9B-F7B ~
 F8B-F12B \\sim F9B-F8B \\sim F8B-F10B \\sim F12B-F10B \\sim F9B-F12B
 with sigma of 0.005
 P2C-F8C \\sim P2C-F10C \\sim P2C-F12C \\sim P2C-F7C \\sim P2C-F9C 
\\sim P2C-F11C \\sim P1C-F4C \\sim P1C-
 F3C \\sim P1C-F1C \\sim P1C-F5C \\sim P1C-F2C \\sim P1C-F6C
 with sigma of 0.005
 F7C-F10C \\sim F8C-F10C \\sim F11C-F10C \\sim F12C-F10C \\sim F7C-F12C 
\\sim F9C-F12C \\sim F8C-F12C
 \\sim F9C-F7C \\sim F7C-F11C \\sim F9C-F8C \\sim F8C-F11C \\sim F9C-F11C
 with sigma of 0.005
 N4-C19B \\sim N4-C19A
 with sigma of 0.005
 N5-C21B \\sim N5-C21A
 with sigma of 0.005
 N6-C22A \\sim N6-C22B
 with sigma of 0.005
 N6-C25A \\sim N6-C25B
 with sigma of 0.005
 N5-C29B \\sim N5-C29A
 with sigma of 0.005
 N4-C24A \\sim N4-C24B
 with sigma of 0.005
 C20B-C19B \\sim C20A-C19A \\sim C24A-C23A \\sim C24B-C23B \\sim C22B-C21B 
\\sim C22A-C21A
 with sigma of 0.005
 P2A-F7A \\sim P2A-F8A \\sim P2A-F9A \\sim P2A-F10A \\sim P2A-F11A 
\\sim P2A-F12A
 with sigma of 0.005
 F9A-F11A \\sim F7A-F10A \\sim F7A-F12A \\sim F9A-F7A \\sim F8A-F7A 
\\sim F8A-F10A \\sim F11A-F10A ~
 F12A-F10A \\sim F9A-F12A \\sim F12A-F11A \\sim F9A-F8A \\sim F8A-F11A 
\\sim F4B-F1B \\sim F3B-F1B ~
 F5B-F1B \\sim F6B-F1B \\sim F4B-F2B \\sim F6B-F2B \\sim F3B-F2B \\sim F5B-F2B 
\\sim F6B-F3B \\sim F4B-F3B
 \\sim F5B-F4B \\sim F6B-F5B
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
F1A \\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim F6A \\sim F1B \\sim F2B 
\\sim F3B \\sim F4B \\sim F5B \\sim F6B \\sim F1C \\sim F2C \\sim F3C 
\\sim F4C \\sim F5C \\sim F6C: 
within 2.3A with sigma of 0.01 and sigma for terminal atoms of 0.02
P1B \\sim P1A \\sim P1C: within 1.7A with sigma of 0.005 and sigma for 
terminal atoms of 0.01
C29A \\sim C29B \\sim C31A \\sim C31B \\sim C30A \\sim C30B \\sim C32A 
\\sim C32B: within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.01
F7B \\sim F8B \\sim F9B \\sim F10B \\sim F11B \\sim F12B \\sim F7A \\sim F8A 
\\sim F9A \\sim F10A \\sim F11A \\sim F12A \\sim F7C \\sim F8C \\sim F9C 
\\sim F10C \\sim F11C \\sim F12C: 
within 2.5A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C23A) = Uanis(C23B)
Uanis(C20A) = Uanis(C20B)
Uanis(C33A) = Uanis(C33B)
Uanis(C35A) = Uanis(C35B)
Uanis(C34A) = Uanis(C34B)
Uanis(C36A) = Uanis(C36B)
Uanis(C26A) = Uanis(C26B)
Uanis(C27A) = Uanis(C27B)
Uanis(C25A) = Uanis(C25B)
Uanis(C19A) = Uanis(C19B)
Uanis(C21A) = Uanis(C21B)
Uanis(C22A) = Uanis(C22B)
Uanis(C28A) = Uanis(C28B)
Uanis(C24A) = Uanis(C24B)
4. Same fragment restrains
{P2A, F7A, F8A, F9A, F10A, F11A, F12A}
as
{P2B, F7B, F8B, F9B, F10B, F11B, F12B}
{P1A, F1A, F2A, F3A, F4A, F5A, F6A}
as
{P1B, F1B, F2B, F3B, F4B, F5B, F6B}
{P1A, F1A, F2A, F3A, F4A, F5A, F6A}
as
{P1C, F1C, F2C, F3C, F4C, F5C, F6C}
5. others
 1*[Sof(P1A)+Sof(F1A)+Sof(F2A)+Sof(F3A)+Sof(F4A)+Sof(F5A)+Sof(F6A)]+1*
 [Sof(P1B)+Sof(F1B)+Sof(F2B)+Sof(F3B)+Sof(F4B)+Sof(F5B)+Sof(F6B)]+1*[Sof(P1C)+
 Sof(F1C)+Sof(F2C)+Sof(F3C)+Sof(F4C)+Sof(F5C)+Sof(F6C)]=1 with esd of 0.01
 1*[Sof(P2A)+Sof(F7A)+Sof(F8A)+Sof(F9A)+Sof(F10A)+Sof(F11A)+Sof(F12A)]+1*
 [Sof(P2B)+Sof(F7B)+Sof(F8B)+Sof(F9B)+Sof(F10B)+Sof(F11B)+Sof(F12B)]+1*
 [Sof(P2C)+Sof(F7C)+Sof(F8C)+Sof(F9C)+Sof(F10C)+Sof(F11C)+Sof(F12C)]=1 with esd
 of 0.01
 Sof(P1A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=FVAR(1)
 Sof(P1B)=Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=FVAR(2)
 Sof(P1C)=Sof(F1C)=Sof(F2C)=Sof(F3C)=Sof(F4C)=Sof(F5C)=Sof(F6C)=FVAR(3)
 Sof(P2A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(F10A)=Sof(F11A)=Sof(F12A)=FVAR(4)
 Sof(P2B)=Sof(F7B)=Sof(F8B)=Sof(F9B)=Sof(F10B)=Sof(F11B)=Sof(F12B)=FVAR(5)
 Sof(P2C)=Sof(F7C)=Sof(F8C)=Sof(F9C)=Sof(F10C)=Sof(F11C)=Sof(F12C)=FVAR(6)
 Fixed Sof: C19A(0.5) H19A(0.5) H19B(0.5) C19B(0.5) H19C(0.5) H19D(0.5)
 C20A(0.5) H20A(0.5) H20B(0.5) C20B(0.5) H20C(0.5) H20D(0.5) C21A(0.5)
 H21A(0.5) H21B(0.5) C21B(0.5) H21C(0.5) H21D(0.5) C22A(0.5) H22A(0.5)
 H22B(0.5) C22B(0.5) H22C(0.5) H22D(0.5) C23A(0.5) H23A(0.5) H23B(0.5)
 C23B(0.5) H23C(0.5) H23D(0.5) C24A(0.5) H24A(0.5) H24B(0.5) C24B(0.5)
 H24C(0.5) H24D(0.5) C25A(0.5) C25B(0.5) C26A(0.5) H26A(0.5) H26B(0.5)
 H26C(0.5) C26B(0.5) H26D(0.5) H26E(0.5) H26F(0.5) C27A(0.5) H27A(0.5)
 H27B(0.5) H27C(0.5) C27B(0.5) H27D(0.5) H27E(0.5) H27F(0.5) C28A(0.5)
 H28A(0.5) H28B(0.5) H28C(0.5) C28B(0.5) H28D(0.5) H28E(0.5) H28F(0.5)
 C29A(0.5) C29B(0.5) C30A(0.5) H30A(0.5) H30B(0.5) H30C(0.5) C30B(0.5)
 H30D(0.5) H30E(0.5) H30F(0.5) C31A(0.5) H31A(0.5) H31B(0.5) H31C(0.5)
 C31B(0.5) H31D(0.5) H31E(0.5) H31F(0.5) C32A(0.5) H32A(0.5) H32B(0.5)
 H32C(0.5) C32B(0.5) H32D(0.5) H32E(0.5) H32F(0.5) C33A(0.5) C33B(0.5)
 C34A(0.5) H34A(0.5) H34B(0.5) H34C(0.5) C34B(0.5) H34D(0.5) H34E(0.5)
 H34F(0.5) C35A(0.5) H35A(0.5) H35B(0.5) H35C(0.5) C35B(0.5) H35D(0.5)
 H35E(0.5) H35F(0.5) C36A(0.5) H36A(0.5) H36B(0.5) H36C(0.5) C36B(0.5)
 H36D(0.5) H36E(0.5) H36F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C19A(H19A,H19B), C19B(H19C,H19D), C20A(H20A,H20B), C20B(H20C,H20D), C21A(H21A,
 H21B), C21B(H21C,H21D), C22A(H22A,H22B), C22B(H22C,H22D), C23A(H23A,H23B),
 C23B(H23C,H23D), C24A(H24A,H24B), C24B(H24C,H24D), C1(H1A,H1B), C2(H2A,H2B),
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
6.b Idealised Me refined as rotating group:
 C26A(H26A,H26B,H26C), C26B(H26D,H26E,H26F), C27A(H27A,H27B,H27C), C27B(H27D,
 H27E,H27F), C28A(H28A,H28B,H28C), C28B(H28D,H28E,H28F), C30A(H30A,H30B,H30C),
 C30B(H30D,H30E,H30F), C31A(H31A,H31B,H31C), C31B(H31D,H31E,H31F), C32A(H32A,
 H32B,H32C), C32B(H32D,H32E,H32F), C34A(H34A,H34B,H34C), C34B(H34D,H34E,H34F),
 C35A(H35A,H35B,H35C), C35B(H35D,H35E,H35F), C36A(H36A,H36B,H36C), C36B(H36D,
 H36E,H36F), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,
 H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_estimated_absorpt_t_max   0.752
_shelx_estimated_absorpt_t_min   0.640
_shelxl_version_number           2013-4