H2CHXdedpa and H4CHXoctapa-Chiral Acyclic Chelating Ligands for (67/68)Ga and (111)In Radiopharmaceuticals.
Ramogida, Caterina F.; Cawthray, Jacqueline F.; Boros, Eszter; Ferreira, Cara L.; Patrick, Brian O.; Adam, Michael J.; Orvig, Chris; Inorganic chemistry 54 (2015) 2017–2031; doi:10.1021/ic502942a

data_4342272
_publ_section_title
;
 H2CHXdedpa and H4CHXoctapa-Chiral Acyclic Chelating Ligands for (67/68)Ga
 and (111)In Radiopharmaceuticals.
;
_journal_issue                   4
_journal_name_full               'Inorganic chemistry'
_journal_page_first              2017
_journal_page_last               2031
_journal_paper_doi               10.1021/ic502942a
_journal_volume                  54
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety
'3(C20 H22 Ga N4 O4), 3(Cl O4), O, 1.62(C H4 O)'
_chemical_formula_sum            'C61.5 H72.5 Cl3 Ga3 N12 O26.5'
_chemical_formula_weight         1719.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.24(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.777(4)
_cell_length_b                   19.775(6)
_cell_length_c                   14.964(5)
_cell_measurement_reflns_used    9798
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.744
_cell_measurement_theta_min      2.143
_cell_volume                     3479(2)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_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    'SIR97 (Burla et al., 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.972
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0976
_diffrn_reflns_av_unetI/netI     0.1007
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            55550
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.308
_diffrn_reflns_theta_min         1.708
_exptl_absorpt_coefficient_mu    1.361
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0810 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.8901.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_description       plate
_exptl_crystal_F_000             1763
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.152
_refine_ls_abs_structure_details
;
 Flack x determined using 3531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     993
_refine_ls_number_reflns         12249
_refine_ls_number_restraints     1139
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0926P)^2^+2.6195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1731
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                9090
_reflns_number_total             12249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic502942a_si_002.cif
_cod_data_source_block           co395
_cod_depositor_comments
'Adding full bibliography for 4342271--4342272.cif.'
_cod_original_formula_sum        'C61.50 H72.50 Cl3 Ga3 N12 O26.50'
_cod_database_code               4342272
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 Cl2B-Cl2
 -0.55 with sigma of 0.02
 Cl1-O13 \\sim Cl1-O14 \\sim Cl1-O15 \\sim Cl1-O16
 with sigma of 0.01
 Cl2-O17 \\sim Cl2-O18 \\sim Cl2-O19 \\sim Cl2-O20
 with sigma of 0.01
 Cl3-O21 \\sim Cl3-O22 \\sim Cl3-O23 \\sim Cl3-O24
 with sigma of 0.01
 Cl3B-O21B \\sim Cl3B-O22B \\sim Cl3B-O23B \\sim Cl3B-O24B
 with sigma of 0.01
 Cl2B-O17B \\sim Cl2B-O18B \\sim Cl2B-O19B \\sim Cl2B-O20B
 with sigma of 0.01
 O17-O18 \\sim O17-O19 \\sim O17-O20 \\sim O18-O19 \\sim O18-O20 \\sim O19-O20
 with sigma of 0.01
 O17B-O18B \\sim O17B-O19B \\sim O17B-O20B \\sim O18B-O19B \\sim O18B-O20B
\\sim O19B-O20B
 with sigma of 0.01
 C62-O27 \\sim C63-O28 \\sim C61-O26
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.2
Uanis(Cl3B) = Uanis(Cl3)
Uanis(Cl2) = Uanis(Cl2B)
Uanis(O20) = Uanis(O20B)
Uanis(O17) = Uanis(O17B)
Uanis(O18) = Uanis(O18B)
Uanis(O19) = Uanis(O19B)
Uanis(O23) = Uanis(O23B)
Uanis(O22) = Uanis(O24B)
Uanis(O24) = Uanis(O21B)
Uanis(O21) = Uanis(O22B)
Uanis(O26) = Uanis(O27) = Uanis(O28)
Uanis(C62) = Uanis(C61) = Uanis(C63)
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(Cl3B)=Sof(O21B)=Sof(O22B)=Sof(O24B)=Sof(O23B)=1-FVAR(1)
 Sof(Cl3)=Sof(O24)=Sof(O23)=Sof(O22)=Sof(O21)=FVAR(1)
 Sof(Cl2B)=Sof(O17B)=Sof(O18B)=Sof(O20B)=Sof(O19B)=1-FVAR(2)
 Sof(O17)=Sof(O18)=Sof(O19)=Sof(O20)=Sof(Cl2)=FVAR(2)
 Sof(O28)=Sof(C63)=Sof(H28A)=Sof(H63A)=Sof(H63B)=Sof(H63C)=1-FVAR(3)
 Sof(O26)=Sof(H26)=Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(H61C)=FVAR(3)
 Sof(O27)=Sof(C62)=Sof(H27)=Sof(H62A)=Sof(H62B)=Sof(H62C)=FVAR(4)
 Fixed X: H27(0.064) H62A(-0.01294) H62B(-0.025751) H62C(0.06967) H61A(-
 0.221531) H61B(-0.0897) H61C(-0.15066) H28A(-0.05265) H63A(-0.05794) H63B(-
 0.12598) H63C(-0.19019)
 Fixed Y: H27(-0.16212) H62A(-0.060391) H62B(-0.11927) H62C(-0.064731)
 H61A(0.086909) H61B(0.09856) H61C(0.086009) H28A(-0.10381) H63A(-0.012421)
 H63B(-0.07127) H63C(-0.016991)
 Fixed Z: H27(1.03733) H62A(1.015201) H62B(0.94522) H62C(0.936829)
 H61A(1.04936) H61B(1.05227) H61C(1.141251) H28A(0.963361) H63A(1.03168)
 H63B(1.0741) H63C(1.01397)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13), C28(H28), C33(H33), C48(H48), C53(H53), N3(H3A), N4(H4A),
 N7(H7), N8(H8A), N11(H11), N12(H12)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C14(H14A,H14B), C27(H27A,H27B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B),
  C32(H32A,H32B), C34(H34A,H34B), C47(H47A,H47B), C49(H49A,H49B), C50(H50A,
 H50B), C51(H51A,H51B), C52(H52A,H52B), C54(H54A,H54B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C23(H23), C24(H24),
 C25(H25), C36(H36), C37(H37), C38(H38), C43(H43), C44(H44), C45(H45), C56(H56),
  C57(H57), C58(H58)
6.d Idealised tetrahedral OH refined as rotating group:
 O26(H26)
;
_shelx_res_checksum              35815
_shelx_hkl_checksum              75682
_olex2_submission_special_instructions 'No special instructions were received'