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_7223476
_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         'C18 H28 Cu N9, 3(Cl O4), H2 O, 0.3(O)'
_chemical_formula_sum            'C18 H30 Cl3 Cu N9 O13.3'
_chemical_formula_weight         755.24
_chemical_name_common            'Copper NOTI complex perchlorate'
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-17
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8317(3)
_cell_length_b                   13.3857(3)
_cell_length_c                   36.8172(9)
_cell_measurement_reflns_used    9513
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      26.56
_cell_measurement_theta_min      2.36
_cell_volume                     5830.9(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            61849
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.065
_diffrn_reflns_theta_min         2.046
_diffrn_source                   'microfocus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0884 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.8197.
The \l/2 correction factor is 0.0000.
;
_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    1.721
_exptl_crystal_description       plate
_exptl_crystal_F_000             3099
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         7053
_refine_ls_number_restraints     680
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0362P)^2^+15.0324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5674
_reflns_number_total             7053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra21131j2.cif
_cod_data_source_block           klinik_mb01_0m
_cod_original_formula_sum        'C18 H30 Cl3 Cu N9 O13.30'
_cod_database_code               7223476
_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 O(H,H) groups
2. Restrained distances
 N5-H5
 0.88 with sigma of 0.02
 N7-H7
 0.88 with sigma of 0.02
 N9B-H9B
 0.91 with sigma of 0.02
 N9A-H9A
 0.91 with sigma of 0.02
 C16A-C15 \\sim C16B-C15
 with sigma of 0.02
 Cl1A-O1A \\sim Cl1A-O4A \\sim Cl1A-O2A \\sim Cl1A-O3A \\sim Cl1B_$1-O4B_$1
\\sim Cl1B_$1-O2B_$1 ~
 Cl1B_$1-O3B_$1 \\sim Cl1B_$1-O1B_$1
 with sigma of 0.02
 Cl3-O9 \\sim Cl3-O10 \\sim Cl3-O12
 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. 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
5. Others
 Sof(Cl1B)=Sof(O1B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=Sof(O9)=Sof(O10)=Sof(N8B)=
 Sof(H8B)=Sof(N9B)=Sof(H9B)=Sof(H15C)=Sof(H15D)=Sof(C16B)=Sof(C17B)=Sof(H17B)=
 Sof(C18B)=Sof(H18B)=Sof(O13B)=Sof(H13C)=Sof(H13D)=Sof(O11)=Sof(O4)=Sof(O13)=1-
 FVAR(1)
 Sof(Cl1A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=Sof(O12)=Sof(O13A)=Sof(H13A)=
 Sof(H13B)=Sof(N8A)=Sof(H8A)=Sof(N9A)=Sof(H9A)=Sof(H15A)=Sof(H15B)=Sof(C16A)=
 Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(O3)=Sof(O1)=Sof(O2)=FVAR(1)
6.a Free rotating group:
 O13A(H13A,H13B), O13B(H13C,H13D)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C11(H11A,H11B), C15(H15A,H15B), C15(H15C,H15D)
6.c Aromatic/amide H refined with riding coordinates:
 N8A(H8A), N8B(H8B), C9(H9), C10(H10), C13(H13), C14(H14), C17A(H17A),
 C17B(H17B), C18A(H18A), C18B(H18B)
;
_shelx_res_checksum              9587
_olex2_submission_special_instructions 'No special instructions were received'