Synthesis,64Cu-labeling and PET imaging of 1,4,7-triazacyclononane derived chelators with pendant azaheterocyclic arms
Gotzmann, Carla; Braun, Friederike; Bartholomä, Mark D; RSC Adv.  (2015) –; doi:10.1039/C5RA21131J

data_7223477
_publ_section_title
;
 Synthesis,64Cu-labeling and PET imaging of 1,4,7-triazacyclononane
 derived chelators with pendant azaheterocyclic arms
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA21131J
_journal_year                    2015
_chemical_formula_moiety
'2(C21 H34 Cu N9), C2 F3 O2, C2 H F3 O2, 5(Cl O4), 4(H2 O)'
_chemical_formula_sum            'C46 H77 Cl5 Cu2 F6 N18 O28'
_chemical_formula_weight         1748.58
_chemical_name_common
'Copper NOTI-MeH complex perchlorate/trifluoroacetate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-01-13 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                62.6910(10)
_cell_angle_beta                 75.1780(10)
_cell_angle_gamma                78.2020(10)
_cell_formula_units_Z            2
_cell_length_a                   10.7732(2)
_cell_length_b                   18.8231(4)
_cell_length_c                   19.6569(5)
_cell_measurement_temperature    100.0(2)
_cell_volume                     3406.35(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle fixed chi diffractometer'
_diffrn_measurement_device_type  'Bruker Apex-II Quazar'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_laue_measured_fraction_full 0.994
_diffrn_reflns_laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            67729
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         1.224
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0713 before and 0.0428 after correction.
The Ratio of minimum to maximum transmission is 0.9391.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_description       plank
_exptl_crystal_F_000             1800
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.458
_refine_diff_density_min         -1.386
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1017
_refine_ls_number_reflns         15562
_refine_ls_number_restraints     1240
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0860P)^2^+7.5785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1599
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12425
_reflns_number_total             15562
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra21131j2.cif
_cod_data_source_block           mb_cg004_0m
_cod_database_code               7223477
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 N15-H15
 0.91 with sigma of 0.02
 N9-H9A
 0.91 with sigma of 0.02
 H26D-H13B
 2.2 with sigma of 0.03
 H26C-O8_$2
 2.1 with sigma of 0.03
 H26D-O15_$3
 2.1 with sigma of 0.03
 H13A-H21_$1 = H13B-H21_$1
 2.2 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(F4B) = Uanis(F6A)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{C46, O21} sigma for 1-2: 0.02, 1-3: 0.04
as
{C44, O23}
7. Others
 Sof(F4B)=Sof(F5B)=Sof(F6B)=Sof(O13B)=Sof(Cl4B)=1-FVAR(1)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(O13A)=Sof(Cl4A)=FVAR(1)
8.a Free rotating group:
 O26(H26C,H26D), O27(H27C,H27D), O28(H28C,H28D), O13(H13A,H13B)
8.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,
 H26B), C28(H28A,H28B), C33(H33A,H33B), C38(H38A,H38B), C1(H1A,H1B), C2(H2A,
 H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C12(H12A,H12B), C17(H17A,H17B)
8.c Aromatic/amide H refined with riding coordinates:
 C30(H30), C31(H31), C35(H35), C36(H36), C40(H40), C41(H41), C9(H9), C10(H10),
 C14(H14), C15(H15A), C19(H19), C20(H20)
8.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C37(H37A,H37B,H37C), C42(H42A,H42B,H42C), C11(H11A,H11B,
 H11C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C)
8.e Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_shelx_res_checksum              33492
_olex2_submission_special_instructions 'No special instructions were received'