#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:08:07 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179678 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/00/7000090.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7000090
loop_
_publ_author_name
'Cui, Xiuling'
'Delgado, Rita'
'Carapuça, Helena M'
'Drew, Michael G. B.'
'Félix, Vítor'
_publ_section_title
;
 Carboxylate anions binding and sensing by a novel tetraazamacrocycle
 containing ferrocene as receptor.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3297
_journal_page_last               3306
_journal_paper_doi               10.1039/b506572k
_journal_year                    2005
_chemical_formula_sum            'C58 H68 Fe2 N4 O12'
_chemical_formula_weight         1124.86
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                100.690(10)
_cell_angle_beta                 109.560(10)
_cell_angle_gamma                96.920(10)
_cell_formula_units_Z            1
_cell_length_a                   9.680(11)
_cell_length_b                   11.633(13)
_cell_length_c                   13.107(16)
_cell_measurement_temperature    293(2)
_cell_volume                     1340(3)
_computing_cell_refinement       XDS
_computing_data_collection       'XDS (Kabsch, 1991)'
_computing_data_reduction        XDS
_computing_molecular_graphics    PLATON(Spek,1994)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device       'Marresearch Image Plate'
_diffrn_measurement_method
'95 frames at 2^o intervals, counting time 2 min.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7789
_diffrn_reflns_theta_full        25.89
_diffrn_reflns_theta_max         25.89
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Walker et al., Acta Cryst 1983 A39 158'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0054(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
  w=1/[σ²(Fo²)+(0.0313P)²+2.0649P] where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                3793
_reflns_number_total             4755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b506572k.txt
_cod_data_source_block           Compound_2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7000090
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.58833(6) 0.92217(4) 0.80954(4) 0.02138(16) Uani 1 d . . .
C11 C 0.4007(4) 0.8360(3) 0.6743(3) 0.0259(8) Uani 1 d . . .
H11 H 0.3920 0.8227 0.6001 0.031 Uiso 1 calc R . .
C12 C 0.4461(4) 0.7581(3) 0.7465(3) 0.0264(8) Uani 1 d . . .
C13 C 0.4446(4) 0.8137(3) 0.8532(3) 0.0331(9) Uani 1 d . . .
H13 H 0.4693 0.7826 0.9160 0.040 Uiso 1 calc R . .
C14 C 0.3992(4) 0.9235(4) 0.8465(3) 0.0377(10) Uani 1 d . . .
H14 H 0.3892 0.9774 0.9044 0.045 Uiso 1 calc R . .
C15 C 0.3712(4) 0.9382(3) 0.7371(3) 0.0332(9) Uani 1 d . . .
H15 H 0.3393 1.0030 0.7106 0.040 Uiso 1 calc R . .
C16 C 0.4884(5) 0.6396(3) 0.7156(3) 0.0343(9) Uani 1 d . . .
H16A H 0.5923 0.6535 0.7224 0.041 Uiso 1 calc R . .
H16B H 0.4798 0.5933 0.7684 0.041 Uiso 1 calc R . .
N17 N 0.3947(3) 0.5682(2) 0.6001(2) 0.0245(6) Uani 1 d . . .
H17A H 0.4234 0.4975 0.5893 0.029 Uiso 1 calc R . .
H17B H 0.4129 0.6067 0.5510 0.029 Uiso 1 calc R . .
C18 C 0.2296(4) 0.5452(4) 0.5754(3) 0.0361(9) Uani 1 d . . .
H18A H 0.1951 0.6202 0.5768 0.043 Uiso 1 calc R . .
H18B H 0.2098 0.5119 0.6328 0.043 Uiso 1 calc R . .
C19 C 0.1438(4) 0.4599(3) 0.4623(3) 0.0273(8) Uani 1 d . . .
C20 C 0.0879(5) 0.4996(3) 0.3656(4) 0.0373(10) Uani 1 d . . .
H20 H 0.1055 0.5809 0.3692 0.045 Uiso 1 calc R . .
C21 C 0.0063(5) 0.4200(4) 0.2641(4) 0.0406(10) Uani 1 d . . .
H21 H -0.0316 0.4481 0.2004 0.049 Uiso 1 calc R . .
C22 C -0.0190(4) 0.2990(4) 0.2570(3) 0.0334(9) Uani 1 d . . .
H22 H -0.0729 0.2460 0.1884 0.040 Uiso 1 calc R . .
C23 C 0.0358(4) 0.2559(3) 0.3520(3) 0.0265(8) Uani 1 d . . .
C24 C 0.1147(4) 0.3375(3) 0.4534(3) 0.0275(8) Uani 1 d . . .
H24 H 0.1491 0.3094 0.5176 0.033 Uiso 1 calc R . .
C25 C 0.0068(4) 0.1234(3) 0.3448(3) 0.0312(9) Uani 1 d . . .
H25A H -0.0699 0.1050 0.3749 0.037 Uiso 1 calc R . .
H25B H -0.0308 0.0803 0.2671 0.037 Uiso 1 calc R . .
N26 N 0.1434(3) 0.0812(3) 0.4068(3) 0.0278(7) Uani 1 d . . .
H26A H 0.1192 0.0018 0.3973 0.033 Uiso 1 calc R . .
H26B H 0.1707 0.1148 0.4800 0.033 Uiso 1 calc R . .
C27 C 0.2765(4) 0.1075(3) 0.3737(3) 0.0293(8) Uani 1 d . . .
H27A H 0.3055 0.1932 0.3864 0.035 Uiso 1 calc R . .
H27B H 0.3595 0.0800 0.4216 0.035 Uiso 1 calc R . .
C28 C 0.2498(4) 0.0512(3) 0.2551(3) 0.0282(8) Uani 1 d . . .
C29 C 0.2852(5) -0.0605(3) 0.2147(4) 0.0363(9) Uani 1 d . . .
H29 H 0.3210 -0.1138 0.2572 0.044 Uiso 1 calc R . .
C30 C 0.2563(5) -0.0759(4) 0.0990(4) 0.0424(11) Uani 1 d . . .
H30 H 0.2697 -0.1412 0.0528 0.051 Uiso 1 calc R . .
C31 C 0.2044(4) 0.0234(4) 0.0660(4) 0.0438(11) Uani 1 d . . .
H31 H 0.1781 0.0358 -0.0056 0.053 Uiso 1 calc R . .
C32 C 0.1989(4) 0.1023(4) 0.1609(3) 0.0347(9) Uiso 1 d . . .
H32 H 0.1674 0.1748 0.1617 0.042 Uiso 1 calc R . .
C41 C 0.4751(4) 0.3217(3) 0.7806(3) 0.0295(8) Uani 1 d . . .
C42 C 0.5972(4) 0.3364(3) 0.7453(3) 0.0265(8) Uani 1 d . . .
C43 C 0.7393(5) 0.3826(4) 0.8258(3) 0.0399(10) Uani 1 d . . .
H43 H 0.8211 0.3900 0.8036 0.048 Uiso 1 calc R . .
C44 C 0.7621(5) 0.4180(4) 0.9380(4) 0.0530(13) Uani 1 d . . .
H44 H 0.8580 0.4499 0.9902 0.064 Uiso 1 calc R . .
C45 C 0.6416(6) 0.4054(4) 0.9721(4) 0.0513(12) Uani 1 d . . .
H45 H 0.6561 0.4290 1.0473 0.062 Uiso 1 calc R . .
C46 C 0.4999(5) 0.3579(4) 0.8943(3) 0.0416(10) Uani 1 d . . .
H46 H 0.4193 0.3498 0.9177 0.050 Uiso 1 calc R . .
C411 C 0.3190(5) 0.2598(4) 0.6988(4) 0.0378(10) Uani 1 d . . .
O412 O 0.3087(3) 0.1757(3) 0.6221(3) 0.0458(8) Uani 1 d . . .
O413 O 0.2095(4) 0.2983(4) 0.7163(3) 0.0728(11) Uani 1 d . . .
C421 C 0.5836(4) 0.3103(3) 0.6251(3) 0.0278(8) Uani 1 d . . .
O422 O 0.6606(3) 0.2417(3) 0.5951(2) 0.0462(8) Uani 1 d . . .
O423 O 0.5030(3) 0.3661(2) 0.5613(2) 0.0318(6) Uani 1 d . . .
O100 O 0.0796(5) -0.1555(3) 0.4083(3) 0.0506(9) Uani 1 d . . .
H101 H 0.141(6) -0.184(5) 0.390(4) 0.058(18) Uiso 1 d . . .
H102 H 0.006(7) -0.195(5) 0.369(5) 0.07(2) Uiso 1 d . . .
O200 O -0.0855(7) 0.6493(5) 0.1366(5) 0.1067(16) Uani 1 d . . .
H200 H -0.1007 0.6694 0.1946 0.128 Uiso 1 calc R . .
C201 C -0.1015(9) 0.7435(8) 0.0787(7) 0.120(3) Uani 1 d . . .
H20A H -0.1252 0.8093 0.1214 0.143 Uiso 1 calc R . .
H20B H -0.1805 0.7147 0.0070 0.143 Uiso 1 calc R . .
H20C H -0.0096 0.7693 0.0693 0.143 Uiso 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C32 Fe C28 41.32(16) 2_666 2_666 ?
C32 Fe C29 68.61(17) 2_666 2_666 ?
C28 Fe C29 41.26(15) 2_666 2_666 ?
C32 Fe C15 164.80(16) 2_666 . ?
C28 Fe C15 125.26(17) 2_666 . ?
C29 Fe C15 105.71(18) 2_666 . ?
C32 Fe C14 153.81(17) 2_666 . ?
C28 Fe C14 164.38(16) 2_666 . ?
C29 Fe C14 127.72(17) 2_666 . ?
C15 Fe C14 40.48(17) . . ?
C32 Fe C11 127.32(16) 2_666 . ?
C28 Fe C11 104.43(18) 2_666 . ?
C29 Fe C11 115.06(18) 2_666 . ?
C15 Fe C11 40.95(15) . . ?
C14 Fe C11 68.47(18) . . ?
C32 Fe C31 40.82(17) 2_666 2_666 ?
C28 Fe C31 69.21(19) 2_666 2_666 ?
C29 Fe C31 68.0(2) 2_666 2_666 ?
C15 Fe C31 151.71(17) . 2_666 ?
C14 Fe C31 120.41(19) . 2_666 ?
C11 Fe C31 167.23(16) . 2_666 ?
C32 Fe C13 120.40(17) 2_666 . ?
C28 Fe C13 151.88(16) 2_666 . ?
C29 Fe C13 166.77(15) 2_666 . ?
C15 Fe C13 68.01(18) . . ?
C14 Fe C13 40.15(17) . . ?
C11 Fe C13 68.45(17) . . ?
C31 Fe C13 111.62(19) 2_666 . ?
C32 Fe C12 108.76(16) 2_666 . ?
C28 Fe C12 116.14(16) 2_666 . ?
C29 Fe C12 149.46(17) 2_666 . ?
C15 Fe C12 68.51(16) . . ?
C14 Fe C12 68.22(16) . . ?
C11 Fe C12 40.77(14) . . ?
C31 Fe C12 130.98(17) 2_666 . ?
C13 Fe C12 40.75(15) . . ?
C32 Fe C30 67.90(18) 2_666 2_666 ?
C28 Fe C30 68.90(17) 2_666 2_666 ?
C29 Fe C30 40.48(18) 2_666 2_666 ?
C15 Fe C30 117.59(18) . 2_666 ?
C14 Fe C30 109.77(17) . 2_666 ?
C11 Fe C30 149.72(17) . 2_666 ?
C31 Fe C30 39.75(18) 2_666 2_666 ?
C13 Fe C30 130.85(18) . 2_666 ?
C12 Fe C30 168.92(17) . 2_666 ?
C12 C11 C15 107.7(3) . . ?
C12 C11 Fe 70.1(2) . . ?
C15 C11 Fe 69.4(2) . . ?
C11 C12 C13 107.4(3) . . ?
C11 C12 C16 126.0(3) . . ?
C13 C12 C16 126.5(3) . . ?
C11 C12 Fe 69.2(2) . . ?
C13 C12 Fe 69.6(2) . . ?
C16 C12 Fe 126.3(3) . . ?
C14 C13 C12 108.2(3) . . ?
C14 C13 Fe 69.5(2) . . ?
C12 C13 Fe 69.7(2) . . ?
C13 C14 C15 108.7(3) . . ?
C13 C14 Fe 70.4(2) . . ?
C15 C14 Fe 69.7(2) . . ?
C14 C15 C11 108.0(3) . . ?
C14 C15 Fe 69.8(2) . . ?
C11 C15 Fe 69.6(2) . . ?
N17 C16 C12 113.9(3) . . ?
C16 N17 C18 114.8(3) . . ?
N17 C18 C19 111.6(3) . . ?
C20 C19 C24 117.7(3) . . ?
C20 C19 C18 122.2(4) . . ?
C24 C19 C18 120.1(3) . . ?
C21 C20 C19 121.0(4) . . ?
C22 C21 C20 120.3(4) . . ?
C21 C22 C23 120.4(4) . . ?
C24 C23 C22 118.5(3) . . ?
C24 C23 C25 121.0(3) . . ?
C22 C23 C25 120.6(3) . . ?
C23 C24 C19 122.2(3) . . ?
N26 C25 C23 112.9(3) . . ?
C25 N26 C27 115.9(3) . . ?
C28 C27 N26 114.2(3) . . ?
C32 C28 C29 106.2(3) . . ?
C32 C28 C27 127.3(3) . . ?
C29 C28 C27 126.3(3) . . ?
C32 C28 Fe 69.2(2) . 2_666 ?
C29 C28 Fe 69.6(2) . 2_666 ?
C27 C28 Fe 121.2(2) . 2_666 ?
C30 C29 C28 108.5(4) . . ?
C30 C29 Fe 70.5(2) . 2_666 ?
C28 C29 Fe 69.1(2) . 2_666 ?
C31 C30 C29 108.6(4) . . ?
C31 C30 Fe 69.7(2) . 2_666 ?
C29 C30 Fe 69.0(2) . 2_666 ?
C30 C31 C32 108.2(4) . . ?
C30 C31 Fe 70.5(2) . 2_666 ?
C32 C31 Fe 68.8(2) . 2_666 ?
C31 C32 C28 108.6(4) . . ?
C31 C32 Fe 70.4(2) . 2_666 ?
C28 C32 Fe 69.5(2) . 2_666 ?
C46 C41 C42 119.2(4) . . ?
C46 C41 C411 119.3(4) . . ?
C42 C41 C411 121.4(3) . . ?
C43 C42 C41 118.5(4) . . ?
C43 C42 C421 117.2(3) . . ?
C41 C42 C421 124.2(3) . . ?
C44 C43 C42 121.7(4) . . ?
C45 C44 C43 119.6(4) . . ?
C46 C45 C44 119.9(4) . . ?
C45 C46 C41 121.1(4) . . ?
O412 C411 O413 125.3(4) . . ?
O412 C411 C41 117.7(4) . . ?
O413 C411 C41 117.0(4) . . ?
O422 C421 O423 123.3(3) . . ?
O422 C421 C42 118.5(3) . . ?
O423 C421 C42 118.0(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe C32 2.030(5) 2_666 ?
Fe C28 2.034(4) 2_666 ?
Fe C29 2.041(4) 2_666 ?
Fe C15 2.044(4) . ?
Fe C14 2.046(4) . ?
Fe C11 2.047(4) . ?
Fe C31 2.051(4) 2_666 ?
Fe C13 2.058(4) . ?
Fe C12 2.059(4) . ?
Fe C30 2.061(4) 2_666 ?
C11 C12 1.430(5) . ?
C11 C15 1.431(5) . ?
C12 C13 1.433(5) . ?
C12 C16 1.507(5) . ?
C13 C14 1.408(6) . ?
C14 C15 1.415(6) . ?
C16 N17 1.496(5) . ?
N17 C18 1.499(5) . ?
C18 C19 1.518(5) . ?
C19 C20 1.390(6) . ?
C19 C24 1.393(5) . ?
C20 C21 1.384(6) . ?
C21 C22 1.379(6) . ?
C22 C23 1.391(5) . ?
C23 C24 1.389(5) . ?
C23 C25 1.514(5) . ?
C25 N26 1.494(5) . ?
N26 C27 1.507(5) . ?
C27 C28 1.491(5) . ?
C28 C32 1.434(5) . ?
C28 C29 1.436(5) . ?
C28 Fe 2.034(4) 2_666 ?
C29 C30 1.419(6) . ?
C29 Fe 2.041(4) 2_666 ?
C30 C31 1.398(6) . ?
C30 Fe 2.061(4) 2_666 ?
C31 C32 1.423(6) . ?
C31 Fe 2.051(4) 2_666 ?
C32 Fe 2.030(5) 2_666 ?
C41 C46 1.400(6) . ?
C41 C42 1.409(5) . ?
C41 C411 1.522(6) . ?
C42 C43 1.390(5) . ?
C42 C421 1.505(5) . ?
C43 C44 1.385(6) . ?
C44 C45 1.384(7) . ?
C45 C46 1.377(6) . ?
C411 O412 1.234(5) . ?
C411 O413 1.272(5) . ?
C421 O422 1.253(4) . ?
C421 O423 1.271(4) . ?
O200 C201 1.439(8) . ?
