Tetracarboxylate Ligands as New Chelates Supporting Copper(II) Paddlewheel-Like Structures.
Gomila, Antoine; Duval, Sylvain; Besnard, Céline; Krämer, Karl W; Liu, Shi-Xia; Decurtins, Silvio; Williams, Alan F.; Inorganic chemistry 53 (2014) 2683–2691; doi:10.1021/ic403077q

data_4337765
_publ_section_title
;
 Tetracarboxylate Ligands as New Chelates Supporting Copper(II)
 Paddlewheel-Like Structures.
;
_journal_issue                   5
_journal_name_full               'Inorganic chemistry'
_journal_page_first              2683
_journal_page_last               2691
_journal_paper_doi               10.1021/ic403077q
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C44 H44 N2 O8'
_chemical_formula_sum            'C44 H44 N2 O8'
_chemical_formula_weight         728.81
_chemical_name_systematic
;
 ?
;
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2013-10-14
_audit_creation_method
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Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                104.260(5)
_cell_angle_beta                 94.848(4)
_cell_angle_gamma                91.927(4)
_cell_formula_units_Z            2
_cell_length_a                   11.6522(5)
_cell_length_b                   12.1177(7)
_cell_length_c                   13.7807(8)
_cell_measurement_reflns_used    3496
_cell_measurement_temperature    220.00(14)
_cell_measurement_theta_max      72.8360
_cell_measurement_theta_min      3.2860
_cell_volume                     1876.12(18)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007). 40, 609-613'
_diffrn_ambient_temperature      220.00(14)
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.9675
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0036221000
_diffrn_orient_matrix_UB_12      0.0284739000
_diffrn_orient_matrix_UB_13      0.1149400000
_diffrn_orient_matrix_UB_21      0.0745044000
_diffrn_orient_matrix_UB_22      -0.1013970000
_diffrn_orient_matrix_UB_23      0.0052943000
_diffrn_orient_matrix_UB_31      0.1101180000
_diffrn_orient_matrix_UB_32      0.0785724000
_diffrn_orient_matrix_UB_33      0.0137001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11918
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.592
_diffrn_reflns_theta_min         3.324
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description
;
;
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.2832
_exptl_crystal_size_mid          0.1865
_exptl_crystal_size_min          0.0630
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     630
_refine_ls_number_reflns         7299
_refine_ls_number_restraints     350
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0706P)^2^+0.1017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1522
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5050
_reflns_number_total             7299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic403077q_si_002.cif
_cod_data_source_block           lig3
_cod_original_cell_volume        1876.11(18)
_cod_database_code               4337765
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'O8 N2 C40'
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C44A, C44B}
3. Restrained distances
 C44B-C45B = C44A-C45A
 1.49 with sigma of 0.02
 C45A-C46A = C46A-C47A = C47A-C48A = C48A-C49A = C49A-C50A
 1.39 with sigma of 0.02
 C45B-C46B = C46B-C47B = C47B-C48B = C48B-C49B = C49B-C50B
 1.39 with sigma of 0.02
 C51A-O52A = C51B-O52B
 1.34 with sigma of 0.02
 C51B-O54B = C51A-O54A
 1.2 with sigma of 0.02
 C51B-C50B = C51A-C50A
 1.49 with sigma of 0.02
 O18B-C19B = O18A-C19A
 1.44 with sigma of 0.02
 O18B-C16 = O18A-C16
 1.34 with sigma of 0.02
 O52A-C53A = O52B-C53B
 1.44 with sigma of 0.02
 O40-C39B = O1-C39A
 1.2 with sigma of 0.02
 C39B-C38 = C39A-C38
 1.49 with sigma of 0.02
 O41A-C39A = O41B-C39B
 1.34 with sigma of 0.01
 O41A-C42A = O41B-C42B
 1.44 with sigma of 0.02
 C45A-C47A = C46A-C48A = C47A-C49A = C48A-C50A = C49A-C45A = C50A-C46A
 2.42 with sigma of 0.04
 C45B-C47B = C46B-C48B = C47B-C49B = C48B-C50B = C49B-C45B = C50B-C46B
 2.42 with sigma of 0.04
 C45B-C51B = C49B-C51B
 2.5 with sigma of 0.04
 C45A-C51A = C49A-C51A
 2.5 with sigma of 0.04
 C51A-C53A
 2.34 with sigma of 0.04
 C51B-C53B
 2.34 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
O18B \\sim C16 \\sim C19B \\sim C19A \\sim O18A: within 1.1A with sigma of 0.04
and sigma for terminal atoms of 0.08
C45A \\sim C46A \\sim C47A \\sim C48A \\sim C49A \\sim C50A \\sim C51A \\sim
O52A \\sim C53A \\sim O54A \\sim C45B \\sim C46B \\sim C47B \\sim C48B \\sim
C49B \\sim C50B \\sim C51B \\sim C53B \\sim O52B \\sim O54B: within 1.1A with
sigma of 0.04 and sigma for terminal atoms of 0.08
O41B \\sim C42B \\sim O40 \\sim C39B \\sim O1 \\sim C39A \\sim O41A \\sim C42A:
within 1A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C44A) = Uanis(C44B)
Uanis(C45B) = Uanis(C45A)
5. Rigid body (RIGU) restrains
 C19A, O18A, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C19B, O18B, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C45A, C46A, C47A, C48A, C49A, C50A, C51A, O52A, C53A, O54A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C45B, C46B, C47B, C48B, C49B, C50B, C51B, C53B, O52B, O54B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O40, C39B, O41B, C42B, C38
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C38, C39A, O1, O41A, C42A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(O18B)=Sof(C19B)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(O1)=Sof(C39A)=Sof(H44C)=
 Sof(H44D)=Sof(C45B)=Sof(C46B)=Sof(H46B)=Sof(C47B)=Sof(H47B)=Sof(C48B)=
 Sof(H48B)=Sof(C49B)=Sof(H49B)=Sof(C50B)=Sof(C51B)=Sof(C53B)=Sof(H53D)=
 Sof(H53E)=Sof(H53F)=Sof(O52B)=Sof(O54B)=1-FVAR(1)
 Sof(O40)=Sof(C39B)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(O18A)=
 Sof(H44A)=Sof(H44B)=Sof(C45A)=Sof(C46A)=Sof(H46A)=Sof(C47A)=Sof(H47A)=
 Sof(C48A)=Sof(H48A)=Sof(C49A)=Sof(H49A)=Sof(C50A)=Sof(C51A)=Sof(O52A)=
 Sof(C53A)=Sof(H53A)=Sof(H53B)=Sof(H53C)=Sof(O54A)=FVAR(1)
 Sof(O41B)=Sof(C42B)=Sof(H42A)=Sof(H42B)=Sof(H42C)=1-FVAR(2)
 Sof(O41A)=Sof(C42A)=Sof(H42D)=Sof(H42E)=Sof(H42F)=FVAR(2)
 Fixed Sof: C44A(0.5) C44B(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C7(H7A,H7B), C9(H9A,H9B), C31(H31A,H31B), C32(H32A,H32B),
 C44A(H44A,H44B), C44A(H44C,H44D)
7.b Me refined with riding coordinates:
 C42B(H42A,H42B,H42C), C53A(H53A,H53B,H53C), C53B(H53D,H53E,H53F), C42A(H42D,
 H42E,H42F)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1), C4(H4), C11(H11), C35(H35), C25(H25), C24(H24), C22(H22),
 C6(H6), C34(H34), C37(H37), C12(H12), C36(H36), C23(H23), C13(H13), C14(H14),
 C46A(H46A), C47A(H47A), C48A(H48A), C49A(H49A), C46B(H46B), C47B(H47B),
 C48B(H48B), C49B(H49B)
7.d Idealised Me refined as rotating group:
 C19B(H19A,H19B,H19C), C30(H30A,H30B,H30C), C19A(H19D,H19E,H19F)
;