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_4336790
_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         'C38 H60 Cu N4, 1(F6 P), 3(C H2 Cl2)'
_chemical_formula_sum            'C41 H66 Cl6 Cu F6 N4 P'
_chemical_formula_weight         1036.18
_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   mixed
_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)
;
_audit_update_record
;
2013-06-12 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 91.378(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6639(17)
_cell_length_b                   15.5299(17)
_cell_length_c                   20.376(2)
_cell_measurement_reflns_used    6532
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.595
_cell_measurement_theta_min      2.462
_cell_volume                     4638.9(9)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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      173.15
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.978
_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  0.0322
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21798
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.915
_diffrn_reflns_theta_min         1.910
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.5566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0583 before and 0.0418 after correction.
The Ratio of minimum to maximum transmission is 0.7470.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       prism
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.291
_platon_squeeze_details
;
TITL CF solution in P21/c
CELL   14.6639   15.5299   20.3760     90.00     91.38     90.00
SPGR P21/c
C101 0.720 0.763 0.765 !      17.16 eA-3
C102 0.874 0.510 0.146 !      14.59 eA-3
C103 0.090 0.214 0.205 !      12.47 eA-3
C104 0.937 0.155 0.602 !      11.92 eA-3
C105 0.544 0.558 0.218 !      11.30 eA-3
C106 0.611 0.507 0.094 !       7.14 eA-3
C107 0.107 0.586 0.833 !       3.46 eA-3
C108 0.364 0.051 0.326 !       2.88 eA-3
C109 0.811 0.818 0.801 !       2.87 eA-3
C110 0.146 0.563 0.879 !       2.26 eA-3
Q111 0.170 0.871 0.100 !       1.28 eA-3
Q112 0.843 0.474 0.342 !       1.17 eA-3
Q113 0.722 0.416 0.283 !       1.05 eA-3
Q114 0.263 0.659 0.714 !       1.03 eA-3
C115 0.707 0.842 0.750 !       0.99 eA-3
C116 0.765 0.027 0.627 !       0.97 eA-3
Q117 0.283 0.681 0.658 !       0.93 eA-3
Q118 0.765 0.496 0.396 !       0.91 eA-3
Q119 0.702 0.478 0.316 !       0.91 eA-3
Q120 0.314 0.865 0.124 !       0.81 eA-3
Q121 0.138 0.851 0.188 !       0.78 eA-3
C122 0.662 0.788 0.798 !       0.73 eA-3
Q123 0.799 0.010 0.777 !       0.70 eA-3
C124 0.863 0.771 0.263 !       0.68 eA-3
C125 0.106 0.675 0.841 !       0.67 eA-3
Q126 0.709 0.032 0.157 !       0.65 eA-3
C127 0.338 0.270 0.204 !       0.61 eA-3
C128 0.782 0.766 0.233 !       0.56 eA-3
Q129 0.170 0.667 0.636 !       0.56 eA-3
Q130 0.701 0.020 0.188 !       0.54 eA-3
Q131 0.248 0.576 0.654 !       0.54 eA-3
Q132 0.889 0.019 0.122 !       0.53 eA-3
C133 0.868 0.320 0.120 !       0.53 eA-3
Q134 0.873 0.137 0.697 !       0.53 eA-3
Q135 0.282 0.433 0.538 !       0.53 eA-3
Q136 0.751 0.346 0.408 !       0.52 eA-3
Q137 0.480 0.923 0.748 !       0.52 eA-3
Q138 0.824 0.906 0.063 !       0.52 eA-3
Q139 0.251 0.602 0.122 !       0.50 eA-3
C140 0.153 0.260 0.170 !       0.50 eA-3
C141 0.468 0.549 0.232 !       0.50 eA-3
;
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     789
_refine_ls_number_reflns         7930
_refine_ls_number_restraints     812
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0664P)^2^+4.6838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6121
_reflns_number_total             7930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic402626p_si_002_09.cif
_cod_data_source_block           at-2-77
_cod_database_code               4336790
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C16-H16A = C16-H16B = C14-H14B = C14-H14A
 0.995 with sigma of 0.005
 C20-H20 = C19-H19A = C19-H19B
 0.995 with sigma of 0.005
 C2-H2B = C2-H2A = C3-H3
 0.995 with sigma of 0.005
 C7-H7B = C7-H7A = C8-H8
 0.995 with sigma of 0.005
 C6-H6A = C6-H6B
 0.995 with sigma of 0.005
 C4-H4B = C4-H4A = C5-H5 = C10-H10A = C10-H10B
 0.995 with sigma of 0.005
 C28-H28A = C28-H28B
 0.995 with sigma of 0.005
 C33-H33A = C33-H33B
 0.995 with sigma of 0.005
 C34-H34B = C34-H34A
 0.995 with sigma of 0.005
 F1B-F4B
 2.246 with sigma of 0.02
 F1B-F5B
 2.246 with sigma of 0.005
 F4B-F6B
 2.246 with sigma of 0.02
 F1B-F4B
 2.246 with sigma of 0.005
 F1A-F3A
 2.246 with sigma of 0.005
 F3A-F4A
 2.246 with sigma of 0.005
 F5A-F2A
 2.246 with sigma of 0.005
 F5A-F1A
 2.246 with sigma of 0.005
 F4A-F5A
 2.246 with sigma of 0.005
 F6A-F2A
 2.246 with sigma of 0.005
 F3A-F6A
 2.246 with sigma of 0.005
 F6C-F3C
 2.246 with sigma of 0.005
 F3C-F1C
 2.246 with sigma of 0.005
 F4C-F1C
 2.246 with sigma of 0.005
 P1C-F6C
 1.583 with sigma of 0.005
 C11-H11B \\sim C11-H11A \\sim C12-H12B \\sim C12-H12A
 with sigma of 0.005
 C24-H24B \\sim C24-H24A \\sim C23-H23B \\sim C23-H23A
 with sigma of 0.005
 C26-H26B \\sim C26-H26A \\sim C27-H27
 with sigma of 0.005
 C30-H30A \\sim C30-H30B \\sim C29-H29
 with sigma of 0.005
 C36-H36B \\sim C36-H36A
 with sigma of 0.005
 C15-H15 \\sim C21-H21A \\sim C21-H21B
 with sigma of 0.005
 C22-H22A \\sim C22-H22B
 with sigma of 0.005
 F3B-F1B \\sim F4B-F1B \\sim F2B-F1B \\sim F5B-F1B \\sim F5B-F2B \\sim F3B-F2B 
\\sim F6B-F2B \\sim F4B-F3B
 \\sim F6B-F3B \\sim F5B-F4B \\sim F6B-F4B \\sim F6B-F5B
 with sigma of 0.005
 F2A-F1A \\sim F5A-F1A \\sim F3A-F1A \\sim F4A-F1A \\sim F5A-F2A \\sim F3A-F2A 
\\sim F6A-F2A \\sim F4A-F3A
 \\sim F6A-F3A \\sim F5A-F4A \\sim F6A-F4A \\sim F6A-F5A
 with sigma of 0.005
 F2C-F1C \\sim F3C-F1C \\sim F4C-F1C \\sim F5C-F1C \\sim F3C-F2C \\sim F5C-F2C 
\\sim F6C-F2C \\sim F4C-F3C
 \\sim F6C-F3C \\sim F6C-F4C \\sim F5C-F4C \\sim F6C-F5C
 with sigma of 0.005
 P1A-F1A \\sim P1A-F2A \\sim P1A-F3A \\sim P1A-F4A \\sim P1A-F5A \\sim P1A-F6A 
\\sim P1B-F1B \\sim P1B-F2B
 \\sim P1B-F3B \\sim P1B-F4B \\sim P1B-F5B \\sim P1B-F6B \\sim P1C-F1C 
\\sim P1C-F2C \\sim P1C-F3C \\sim P1C-F4C \\sim P1C-F5C \\sim P1C-F6C
 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 1.7A with sigma of 0.004 and sigma for 
terminal atoms of 0.006
Uiso(H16B) = Uiso(H16A) = Uiso(H14B) = Uiso(H14A)
Uiso(H12B) = Uiso(H12A) = Uiso(H11A) = Uiso(H11B)
Uiso(H23B) = Uiso(H23A) = Uiso(H24B) = Uiso(H24A)
Uiso(H17) = Uiso(H18B) = Uiso(H18A)
Uiso(H26A) = Uiso(H26B) = Uiso(H27)
Uiso(H30A) = Uiso(H30B) = Uiso(H29)
Uiso(H6A) = Uiso(H6B)
Uiso(H4B) = Uiso(H4A) = Uiso(H5) = Uiso(H10A) = Uiso(H10B)
4. Same fragment restrains
{P1A, F1A, F2A, F3A, F4A, F5A, F6A}
as
{P1B, F1B, F2B, F3B, F4B, F5B, F6B}
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
 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)
6.a Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C)
;
_shelxl_version_number           2013-4