Reinforced Ni(II)-cyclam derivatives as dual 1H/19F MRI Probes
Pujales-Paradela, Rosa; Savić, Tanja; Brandariz, Isabel; Pérez-Lourido, Paulo; Angelovski, Goran; Esteban, David; Platas-Iglesias, Carlos; Chemical Communications  (2019) –; doi:10.1039/C9CC01204D

data_7123121
_publ_section_title
;
 Reinforced Ni(II)-cyclam derivatives as dual 1H/19F MRI Probes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01204D
_journal_year                    2019
_chemical_formula_moiety         'C23 H33 F3 N5 Ni O3, Cl'
_chemical_formula_sum            'C21 H32 Cl2 F3 N5 Ni O'
_chemical_formula_weight         557.12
_chemical_name_systematic        Ni59Cl
_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   geom
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-18 deposited with the CCDC.    2019-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                84.577(2)
_cell_angle_beta                 84.097(2)
_cell_angle_gamma                73.547(2)
_cell_formula_units_Z            4
_cell_length_a                   11.1218(9)
_cell_length_b                   15.1505(11)
_cell_length_c                   20.4174(14)
_cell_measurement_reflns_used    9581
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.38
_cell_volume                     3274.3(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_radiation_source         'Incoatec high brillance I\muS microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            199677
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.346
_diffrn_reflns_theta_min         2.372
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1652 before and 0.0854 after correction.
The Ratio of minimum to maximum transmission is 0.7604.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.379
_exptl_crystal_size_min          0.213
_platon_squeeze_details
;
TITL 32011501_0m_a.res in P-1
CELL   11.1218   15.1505   20.4174     84.58     84.10     73.55
SPGR P-1
C101 0.717 0.723 0.110 !      17.87 eA-3
C102 0.999 0.446 0.198 !      14.92 eA-3
Q103 0.903 0.638 0.018 !      13.27 eA-3
Q104 0.687 0.897 0.146 !      13.09 eA-3
C105 0.424 0.906 0.015 !      10.62 eA-3
C106 0.485 0.020 0.099 !      10.40 eA-3
Q107 0.066 0.271 0.278 !      10.33 eA-3
C108 0.595 0.036 0.426 !       9.58 eA-3
C109 0.419 0.995 0.278 !       9.04 eA-3
C110 0.122 0.189 0.057 !       8.21 eA-3
C111 0.343 0.069 0.399 !       8.19 eA-3
C112 0.203 0.993 0.501 !       8.05 eA-3
C113 0.779 0.958 0.030 !       7.40 eA-3
C114 0.189 0.255 0.393 !       6.40 eA-3
C115 0.935 0.126 0.454 !       5.66 eA-3
C116 0.859 0.166 0.465 !       5.57 eA-3
C117 0.080 0.193 0.499 !       5.44 eA-3
Q118 0.048 0.273 0.203 !       3.89 eA-3
Q119 0.592 0.237 0.500 !       3.65 eA-3
Q120 0.346 0.073 0.075 !       3.64 eA-3
Q121 0.393 0.268 0.484 !       3.62 eA-3
Q122 0.425 0.844 0.470 !       3.53 eA-3
Q123 0.091 0.499 0.074 !       3.40 eA-3
Q124 0.468 0.272 0.486 !       3.34 eA-3
Q125 0.340 0.546 0.465 !       3.21 eA-3
Q126 0.999 0.838 0.262 !       3.17 eA-3
Q127 0.238 0.626 0.454 !       3.03 eA-3
Q128 0.639 0.820 0.472 !       2.69 eA-3
Q129 0.251 0.166 0.197 !       2.59 eA-3
Q130 0.440 0.732 0.072 !       2.47 eA-3
Q131 0.077 0.834 0.221 !       2.23 eA-3
Q132 0.292 0.136 0.172 !       2.09 eA-3
Q133 0.142 0.524 0.047 !       2.04 eA-3
Q134 0.502 0.672 0.051 !       1.93 eA-3
Q135 0.548 0.856 0.468 !       1.84 eA-3
Q136 0.661 0.348 0.187 !       1.66 eA-3
C137 0.346 0.036 0.351 !       1.63 eA-3
Q138 0.373 0.466 0.455 !       1.63 eA-3
Q139 0.151 0.628 0.441 !       1.54 eA-3
Q140 0.561 0.367 0.199 !       1.54 eA-3
Q141 0.112 0.853 0.078 !       1.41 eA-3
Q142 0.282 0.687 0.208 !       1.37 eA-3
Q143 0.204 0.818 0.379 !       1.36 eA-3
Q144 0.764 0.491 0.141 !       1.31 eA-3
Q145 0.250 0.147 0.265 !       1.30 eA-3
Q146 0.858 0.921 0.359 !       1.29 eA-3
Q147 0.371 0.307 0.152 !       1.27 eA-3
C148 0.247 0.046 0.449 !       1.25 eA-3
Q149 0.702 0.546 0.108 !       1.24 eA-3
Q150 0.970 0.033 0.222 !       1.23 eA-3
Q151 0.952 0.814 0.106 !       1.22 eA-3
Q152 0.703 0.985 0.278 !       1.20 eA-3
Q153 0.204 0.712 0.141 !       1.17 eA-3
Q154 0.970 0.560 0.264 !       1.16 eA-3
C155 0.126 0.220 0.328 !       1.15 eA-3
Q156 0.642 0.705 0.098 !       1.14 eA-3
C157 0.836 0.670 0.046 !       1.13 eA-3
Q158 0.234 0.869 0.360 !       1.12 eA-3
Q159 0.234 0.748 0.325 !       1.12 eA-3
Q160 0.173 0.553 0.404 !       1.12 eA-3
Q161 0.874 0.993 0.329 !       1.10 eA-3
Q162 0.046 0.847 0.389 !       1.10 eA-3
Q163 0.294 0.309 0.269 !       1.08 eA-3
Q164 0.563 0.268 0.057 !       1.07 eA-3
Q165 0.767 0.220 0.091 !       1.06 eA-3
Q166 0.906 0.577 0.376 !       1.06 eA-3
Q167 0.627 0.313 0.360 !       1.05 eA-3
Q168 0.874 0.472 0.365 !       1.05 eA-3
Q169 0.098 0.909 0.377 !       1.05 eA-3
Q170 0.687 0.647 0.189 !       1.05 eA-3
Q171 0.683 0.221 0.139 !       1.03 eA-3
Q172 0.063 0.953 0.204 !       1.01 eA-3
Q173 0.581 0.736 0.397 !       1.00 eA-3
Q174 0.908 0.692 0.186 !       1.00 eA-3
Q175 0.563 0.621 0.401 !       0.99 eA-3
Q176 0.842 0.463 0.447 !       0.99 eA-3
Q177 0.856 0.347 0.105 !       0.98 eA-3
Q178 0.359 0.366 0.087 !       0.97 eA-3
Q179 0.831 0.446 0.420 !       0.97 eA-3
Q180 0.206 0.468 0.402 !       0.97 eA-3
Q181 0.030 0.757 0.064 !       0.95 eA-3
Q182 0.720 0.289 0.012 !       0.95 eA-3
Q183 0.062 0.959 0.106 !       0.94 eA-3
Q184 0.595 0.516 0.348 !       0.92 eA-3
Q185 1.003 0.252 0.295 !       0.92 eA-3
Q186 0.314 0.825 0.201 !       0.91 eA-3
Q187 0.221 0.960 0.186 !       0.90 eA-3
Q188 0.856 0.250 0.344 !       0.90 eA-3
Q189 0.405 0.324 0.351 !       0.89 eA-3
Q190 0.858 0.564 0.450 !       0.89 eA-3
Q191 0.360 0.475 0.221 !       0.89 eA-3
Q192 0.436 0.401 0.332 !       0.89 eA-3
Q193 0.934 0.436 0.325 !       0.88 eA-3
Q194 0.592 0.851 0.341 !       0.88 eA-3
Q195 0.579 0.408 0.044 !       0.87 eA-3
Q196 0.017 0.665 0.171 !       0.87 eA-3
Q197 0.965 0.973 0.124 !       0.86 eA-3
Q198 0.815 0.391 0.048 !       0.85 eA-3
C199 0.794 0.700 0.075 !       0.83 eA-3
;
_refine_diff_density_max         1.468
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         16341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0568P)^2^+8.3222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1415
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15207
_reflns_number_total             16341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01204d2.cif
_cod_data_source_block           32011501_0m_sq
_cod_database_code               7123121
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.850
_shelx_estimated_absorpt_t_min   0.746
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F5) = Uanis(F6) = Uanis(F4)
Uanis(F8) = Uanis(F7) = Uanis(F9)
Uanis(F10) = Uanis(F12) = Uanis(F11)
3. Others
 Sof(Cl3)=1-FVAR(1)
 Sof(Cl2)=FVAR(1)
 Fixed Sof: F4(0.44) F5(0.44) F6(0.44) F7(0.36) F8(0.36) F9(0.36) F10(0.2)
 F11(0.2) F12(0.2)
4.a 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), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C24(H24A,H24B), C25(H25A,H25B),
  C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,
 H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C36(H36A,H36B), C38(H38A,H38B)
4.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C21(H21), C22(H22), N5(H5), C41(H41), C42(H42), C44(H44),
 C45(H45), N10(H10)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'