A Polyaromatic Terdentate Binding Unit with Fused 5,6-Membered Chelates for Complexing s-, p-, d-, and f-Block Cations
Thi Nhu Y Hoang; Marie Humbert-Droz; Thibault Dutronc; Laure Guénée; Céline Besnard; Claude Piguet; Inorganic Chemistry 52 (2013) 5570–5580; doi:10.1021/ic400526j

data_4334793
_publ_contact_author_address
;Department of inorganic, analytic and applied chemistry 
University of Geneva, Sciences II 
30 quai Ernest-Ansermet 
CH-1211 Gen\`eve 4 
;
_publ_contact_author_email       claude.Piguet@unige.ch
_publ_contact_author_fax         '+41 (0)22 379 68 30 '
_publ_contact_author_name        'Claude Piguet'
_publ_contact_author_phone       '+41 (0)22 379 60 34'
_publ_section_title
;
 A Polyaromatic Terdentate Binding Unit with Fused 5,6-Membered Chelates
 for Complexing s-, p-, d-, and f-Block Cations
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5570
_journal_page_last               5580
_journal_paper_doi               10.1021/ic400526j
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         '1(C34 H24 N8 Zn), 2(C F3 O3 S), 0.13(H2 O)'
_chemical_formula_sum            'C36 H24.25 F6 N8 O6.12 S2 Zn'
_chemical_formula_weight         910.37
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-24
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                76.931(2)
_cell_angle_beta                 86.061(2)
_cell_angle_gamma                84.064(2)
_cell_formula_units_Z            4
_cell_length_a                   12.7973(4)
_cell_length_b                   13.0890(3)
_cell_length_c                   22.9289(7)
_cell_measurement_reflns_used    11595
_cell_measurement_temperature    180.1
_cell_measurement_theta_max      73.1952
_cell_measurement_theta_min      3.4742
_cell_volume                     3717.07(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      180.1
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega   -5.00   43.00   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5475   38.0000    0.0000 60

  2 omega -124.00  -99.20   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5475  -99.0000  150.0000 31

  3 omega  -49.00  -21.00   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5475   38.0000    0.0000 35

  4 omega  -28.00   34.40   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5475   38.0000  150.0000 78

  5 omega  -99.00   -3.80   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5475  -38.0000 -180.0000 119

  6 omega -109.00  -36.20   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5475  178.0000  -30.0000 91

  7 omega   62.00  130.00   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       37.5475 -178.0000   90.0000 85

  8 omega   85.00  128.20   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       37.5475  178.0000  -60.0000 54

  9 omega  -15.00   11.40   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -68.5000   30.0000 -120.0000 33

 10 omega   32.00   85.60   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639  -30.0000  -60.0000 67

 11 omega   62.00  113.20   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639 -111.0000  150.0000 64

 12 omega   27.00  147.00   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639  -77.0000  -30.0000 150

 13 omega   66.00   99.60   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639  -45.0000  -30.0000 42

 14 omega   29.00  108.20   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639  -94.0000 -150.0000 99

 15 omega   36.00   92.00   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639  -45.0000 -180.0000 70

 16 omega   79.00  115.80   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639 -111.0000  -30.0000 46

 17 omega   25.00   78.60   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639  -94.0000  -60.0000 67

 18 omega   29.00   57.80   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639  -30.0000   30.0000 36

 19 omega   77.00  169.00   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639   45.0000  -30.0000 115

 20 omega   30.00   87.60   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639  -30.0000   60.0000 72

 21 omega   35.00   82.20   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639 -111.0000 -180.0000 59

 22 omega   45.00  171.40   0.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7639    0.0000  -60.0000 158
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0324222000
_diffrn_orient_matrix_UB_12      -0.1182575000
_diffrn_orient_matrix_UB_13      0.0050348000
_diffrn_orient_matrix_UB_21      -0.0478058000
_diffrn_orient_matrix_UB_22      -0.0240877000
_diffrn_orient_matrix_UB_23      0.0646310000
_diffrn_orient_matrix_UB_31      -0.1065474000
_diffrn_orient_matrix_UB_32      -0.0126878000
_diffrn_orient_matrix_UB_33      -0.0238234000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25902
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         73.29
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    2.767
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1845
_exptl_crystal_size_max          0.2934
_exptl_crystal_size_mid          0.1015
_exptl_crystal_size_min          0.0382
_refine_diff_density_max         1.395
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1225
_refine_ls_number_reflns         14506
_refine_ls_number_restraints     290
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+3.8729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                12329
_reflns_number_total             14506
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic400526j_si_002_7.cif
_cod_data_source_block           8
_cod_original_cell_volume        3717.06(18)
_cod_database_code               4334793
_chemical_oxdiff_formula         'Zn1 S2 O6.125 N8 F6 H24.25 C36'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H32B of C32B, H31B of C31B, H3A of C3A, H22 of C22, H3 of C3, H14A of C14A,
  H14 of C14, H26 of C26, H17A of C17A, H10 of C10, H19 of C19, H27 of C27, H6A
  of C6A, H18 of C18, H2A of C2A, H11 of C11, H33 of C33, H1A of C1A, H11A of
  C11A, H17 of C17, H34 of C34, H1 of C1, H23 of C23, H28 of C28, H9A of C9A,
  H9 of C9, H20 of C20, H15 of C15, H6 of C6, H31 of C31, H5A of C5A, H10A of
  C10A, H16 of C16, H2 of C2, H32 of C32, H15A of C15A, H5 of C5, H33B of C33B,
  H34B of C34B, H26B of C26B, H27B of C27B, H28B of C28B, H23B of C23B, H22B of
  C22B, H20B of C20B, H19B of C19B, H18B of C18B, H33A of C33A, H34A of C34A,
  H32A of C32A, H31A of C31A, H26A of C26A, H27A of C27A, H28A of C28A, H23A of
  C23A, H22A of C22A, H20A of C20A, H19A of C19A, H18A of C18A, H16A of C16A
 At 1.5 times of:
  {H1B,H1C} of O1
2. Restrained distances
 O11A-O12B ~ O12B-O10B
 with sigma of 0.04
 S9B-O11A ~ S9B-O12B ~ S9B-O10B ~ S9A-O10A ~ S9A-O11B ~ S9A-O12A
 with sigma of 0.02
 C1E-F15A ~ C1E-F16A ~ C1E-F14A ~ C0AA-F16B ~ C0AA-F15B ~ C0AA-F14B
 with sigma of 0.02
 S9A-C1E ~ S9B-C0AA
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C20B ~ C32A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
S9B ~ O10B ~ O12B ~ F16B ~ F15B ~ O11B ~ F14B ~ C0AA ~ S9A ~ O10A ~ O11A 
~ O12A ~ C1E ~ F16A ~ F15A ~ F14A: within 1.7A with sigma of 0.04 and sigma 
for terminal atoms of 0.08
4. Same fragment restrains
{N5A, C18A, C19A, C20A, C21A, C22A, C23A, N6A, C24A, C25A, N7A, C29A, C28A, 
C27A, C26A, C30A, N8A}
as
{N5B, C18B, C19B, C20B, C21B, C22B, C23B, N6B, C24B, C25B, N7B, C29B, C28B, 
C27B, C26B, C30B, N8B}
5. others
 Sof(N5A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=
 Sof(C21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(N6A)=Sof(C24A)=Sof(C25A)=
 Sof(N7A)=Sof(C29A)=Sof(C28A)=Sof(H28A)=Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=
 Sof(C30A)=Sof(N8A)=Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=Sof(C34A)=Sof(H34A)=
 Sof(C33A)=Sof(H33A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-
 Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-
 Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-
 Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-
 Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-
 Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)=1-Sof(C18A)
 1-Sof(O10B)=1-Sof(O10B)=1-Sof(O10B)=1-Sof(O10B)=1-Sof(O10B)=Sof(O11B)=1-
 Sof(O10B)=1-Sof(O10B)=Sof(S9A)=Sof(O10A)=1-Sof(O10B)=Sof(O12A)=Sof(C1E)=
 Sof(F16A)=Sof(F15A)=Sof(F14A)
 Fixed Sof: O1(0.25) H1B(0.25) H1C(0.25)
6.a Riding coordinates:
 O1(H1B,H1C)
6.b Aromatic/amide H refined with riding coordinates:
 C9A(H9A), C28(H28), C23(H23), C1(H1), C34(H34), C17(H17), C11A(H11A),
 C1A(H1A), C33(H33), C11(H11), C2A(H2A), C18(H18), C6A(H6A), C27(H27), C19(H19),
  C10(H10), C17A(H17A), C26(H26), C14(H14), C14A(H14A), C3(H3), C22(H22),
 C3A(H3A), C9(H9), C20(H20), C15(H15), C6(H6), C31(H31), C5A(H5A), C10A(H10A),
 C16(H16), C2(H2), C32(H32), C15A(H15A), C5(H5), C16A(H16A), C18A(H18A),
 C19A(H19A), C20A(H20A), C22A(H22A), C23A(H23A), C28A(H28A), C27A(H27A),
 C26A(H26A), C31A(H31A), C32A(H32A), C34A(H34A), C33A(H33A), C18B(H18B),
 C19B(H19B), C20B(H20B), C22B(H22B), C23B(H23B), C28B(H28B), C27B(H27B),
 C26B(H26B), C34B(H34B), C33B(H33B), C32B(H32B), C31B(H31B)
;