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_4337766
_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_absolute_configuration ad
_chemical_formula_moiety         '3(Cl), C40 H38 N2 O8, C2 H8 N, 2(C3 H7 N O)'
_chemical_formula_sum            'C48 H60 Cl3 N5 O10'
_chemical_formula_weight         973.36
_chemical_name_systematic
;
 ?
;
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-10-14
_audit_creation_method
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Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
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_cell_angle_alpha                90
_cell_angle_beta                 94.351(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9478(3)
_cell_length_b                   15.3695(3)
_cell_length_c                   15.1896(4)
_cell_measurement_reflns_used    5624
_cell_measurement_temperature    192(3)
_cell_measurement_theta_max      73.3930
_cell_measurement_theta_min      4.0170
_cell_volume                     2548.47(11)
_computing_cell_refinement
;
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      192(3)
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.7022
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0046516000
_diffrn_orient_matrix_UB_12      0.0389412000
_diffrn_orient_matrix_UB_13      0.0931048000
_diffrn_orient_matrix_UB_21      -0.1380126000
_diffrn_orient_matrix_UB_22      0.0176596000
_diffrn_orient_matrix_UB_23      -0.0187137000
_diffrn_orient_matrix_UB_31      -0.0289605000
_diffrn_orient_matrix_UB_32      -0.0907465000
_diffrn_orient_matrix_UB_33      0.0362816000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10029
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         73.317
_diffrn_reflns_theta_min         2.918
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.307
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       plate
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.6876
_exptl_crystal_size_mid          0.5071
_exptl_crystal_size_min          0.1197
_platon_squeeze_details
;
;
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         7204
_refine_ls_number_restraints     141
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0512
_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^)+(0.1038P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1486
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                6598
_reflns_number_total             7204
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic403077q_si_002.cif
_cod_data_source_block           lig_5
_cod_database_code               4337766
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H19 of C19, H21 of C21, H22 of C22, H3 of C3, H48 of C48,
   H45 of C45, H41 of C41, H40 of C40, H37 of C37, H36 of C36, H34 of C34, H32
  of C32, H29 of C29, H25 of C25, H24 of C24, H14 of C14, H13 of C13, H1B of
  C1B, H1D of C1D, H5 of C5, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H6A of C6, H9 of C9, All O(H) groups
2. Restrained distances
 O3-C6 = O-C9
 1.22 with sigma of 0.02
 N2-C9 = N4-C6
 1.36 with sigma of 0.02
 N2-C10 = N4-C8 = N2-C11 = N4-C7
 1.45 with sigma of 0.02
 O3-N4
 2.3 with sigma of 0.04
 O-N2
 2.3 with sigma of 0.04
 C6-C8
 2.45 with sigma of 0.04
 C6-C7
 2.45 with sigma of 0.04
 C10-C9
 2.45 with sigma of 0.04
 C11-C9
 2.45 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O3 \\sim C6 \\sim N4 \\sim C7 \\sim C8 \\sim C11 \\sim O \\sim C9 \\sim N2
\\sim C10: within 1A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(N2) \\sim Ueq, Uanis(O) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(C11) \\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C6)
\\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
4. Rigid body (RIGU) restrains
 O3, C6, N4, C7, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O, C9, N2, C10, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O3(0.4) C6(0.4) H6A(0.4) N4(0.4) C7(0.4) H7A(0.4) H7B(0.4)
 H7C(0.4) C8(0.4) H8A(0.4) H8B(0.4) H8C(0.4) O(0.3) C9(0.3) H9(0.3) N2(0.3)
 C10(0.3) H10A(0.3) H10B(0.3) H10C(0.3) C11(0.3) H11A(0.3) H11B(0.3) H11C(0.3)
6.a Ternary CH refined with riding coordinates:
 N7(H7), N10(H10)
6.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C23(H23A,H23B), C27(H27A,H27B), C28(H28A,H28B), C46(H46A,
 H46B), C1C(H1CA,H1CB), N1(H1C,H1E)
6.c Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
6.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C29(H29),
 C32(H32), C34(H34), C36(H36), C37(H37), C40(H40), C41(H41), C45(H45), C48(H48),
  C3(H3), C13(H13), C1B(H1B), C1D(H1D), C5(H5), C6(H6A), C9(H9)
6.e Tetrahedral OH refined with riding coordinates:
 O11(H11)
6.f Idealised Me refined as rotating group:
 C1(H1F,H1G,H1H), C4(H4A,H4B,H4C)
6.g Idealised tetrahedral OH refined as rotating group:
 O6(H6), O8(H8), O1A(H1A)
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