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#$Date: 2016-03-21 18:03:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178800 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/54/4105425.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_4105425
loop_
_publ_author_name
'Lei-lei Tian'
'Chun Wang'
'Sandipan Dawn'
'Mark D. Smith'
'Jeanette A. Krause'
'Linda S. Shimizu'
_publ_contact_author_address
;
Department of Chemistry and Biochemistry
University of South Carolina
Columbia, South Carolina 29208
USA
;
_publ_contact_author_email       shimizul@mail.chem.sc.edu
_publ_contact_author_fax         '1 803 777 9521'
_publ_contact_author_name        'Professor Linda S. Shimizu'
_publ_contact_author_phone       '1 803 777 2066'
_publ_section_title
;
 Macrocycles with Switchable exo/endo Metal Binding Sites
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17620
_journal_page_last               17629
_journal_paper_doi               10.1021/ja906474z
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C26 H24 N8 O2'
_chemical_formula_sum            'C26 H24 N8 O2'
_chemical_formula_weight         480.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.4400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4446(5)
_cell_length_b                   10.3582(6)
_cell_length_c                   13.2736(8)
_cell_measurement_reflns_used    7158
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.309
_cell_measurement_theta_min      2.502
_cell_volume                     1119.15(11)
_computing_cell_refinement       'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_data_collection       'SMART Version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_molecular_graphics    various
_computing_publication_material  'SHELXTL Version 6.14 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_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  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15984
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0475P)²+0.2680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                1956
_reflns_number_total             2283
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja906474z_si_001_2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4105425
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.26881(15) 0.60501(12) 0.08995(8) 0.0226(3) Uani 1 1 d .
C2 C 0.01138(16) 0.56817(13) 0.13166(10) 0.0284(3) Uani 1 1 d .
H2A H -0.0080 0.4866 0.0913 0.034 Uiso 1 1 calc R
H2B H -0.0962 0.6113 0.1225 0.034 Uiso 1 1 calc R
C3 C 0.08210(15) 0.53646(12) 0.24658(9) 0.0248(3) Uani 1 1 d .
C4 C 0.01973(15) 0.43502(13) 0.29230(10) 0.0260(3) Uani 1 1 d .
H4 H -0.0672 0.3862 0.2487 0.031 Uiso 1 1 calc R
C5 C 0.19619(15) 0.46887(12) 0.45406(9) 0.0233(3) Uani 1 1 d .
C6 C 0.27150(16) 0.56876(13) 0.41427(10) 0.0273(3) Uani 1 1 d .
H6 H 0.3625 0.6131 0.4582 0.033 Uiso 1 1 calc R
C7 C 0.21333(16) 0.60318(13) 0.31054(10) 0.0281(3) Uani 1 1 d .
H7 H 0.2629 0.6723 0.2830 0.034 Uiso 1 1 calc R
C8 C 0.25322(15) 0.43179(12) 0.56627(9) 0.0227(3) Uani 1 1 d .
C9 C 0.38211(16) 0.49477(12) 0.73420(10) 0.0247(3) Uani 1 1 d .
H9 H 0.4325 0.5610 0.7814 0.030 Uiso 1 1 calc R
C10 C 0.36991(15) 0.37242(12) 0.77508(9) 0.0235(3) Uani 1 1 d .
C11 C 0.29413(16) 0.27773(12) 0.70491(10) 0.0268(3) Uani 1 1 d .
H11 H 0.2839 0.1925 0.7288 0.032 Uiso 1 1 calc R
C12 C 0.23326(16) 0.30747(12) 0.59986(10) 0.0266(3) Uani 1 1 d .
H12 H 0.1787 0.2437 0.5516 0.032 Uiso 1 1 calc R
C13 C 0.44356(16) 0.34248(13) 0.88982(9) 0.0260(3) Uani 1 1 d .
H13A H 0.4348 0.4198 0.9319 0.031 Uiso 1 1 calc R
H13B H 0.3801 0.2720 0.9111 0.031 Uiso 1 1 calc R
N1 N 0.38412(13) 0.69598(11) 0.08841(8) 0.0256(3) Uani 1 1 d .
H1 H 0.3624(19) 0.7793(17) 0.1030(12) 0.040(4) Uiso 1 1 d .
N2 N 0.11656(13) 0.65074(11) 0.08923(8) 0.0261(3) Uani 1 1 d .
H2 H 0.1006(19) 0.7339(16) 0.0922(11) 0.033(4) Uiso 1 1 d .
N3 N 0.07179(13) 0.40031(10) 0.39252(8) 0.0261(3) Uani 1 1 d .
N4 N 0.32779(13) 0.52528(10) 0.63312(8) 0.0240(2) Uani 1 1 d .
O1 O 0.29764(11) 0.48866(8) 0.09110(7) 0.0275(2) Uani 1 1 d .
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'
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
O1 C1 N1 122.67(12) . .
O1 C1 N2 121.50(12) . .
N1 C1 N2 115.83(11) . .
N2 C2 C3 113.57(11) . .
N2 C2 H2A 108.9 . .
C3 C2 H2A 108.9 . .
N2 C2 H2B 108.9 . .
C3 C2 H2B 108.9 . .
H2A C2 H2B 107.7 . .
C4 C3 C7 116.39(11) . .
C4 C3 C2 120.68(11) . .
C7 C3 C2 122.91(12) . .
N3 C4 C3 125.32(12) . .
N3 C4 H4 117.3 . .
C3 C4 H4 117.3 . .
N3 C5 C6 121.55(11) . .
N3 C5 C8 117.56(11) . .
C6 C5 C8 120.88(11) . .
C7 C6 C5 119.61(12) . .
C7 C6 H6 120.2 . .
C5 C6 H6 120.2 . .
C6 C7 C3 119.74(12) . .
C6 C7 H7 120.1 . .
C3 C7 H7 120.1 . .
N4 C8 C12 121.97(11) . .
N4 C8 C5 116.26(11) . .
C12 C8 C5 121.76(11) . .
N4 C9 C10 124.43(11) . .
N4 C9 H9 117.8 . .
C10 C9 H9 117.8 . .
C11 C10 C9 116.79(11) . .
C11 C10 C13 121.52(11) . .
C9 C10 C13 121.62(11) . .
C12 C11 C10 119.99(12) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C8 119.03(11) . .
C11 C12 H12 120.5 . .
C8 C12 H12 120.5 . .
N1 C13 C10 112.02(10) 3_666 .
N1 C13 H13A 109.2 3_666 .
C10 C13 H13A 109.2 . .
N1 C13 H13B 109.2 3_666 .
C10 C13 H13B 109.2 . .
H13A C13 H13B 107.9 . .
C1 N1 C13 119.19(11) . 3_666
C1 N1 H1 117.8(10) . .
C13 N1 H1 117.5(10) 3_666 .
C1 N2 C2 117.69(11) . .
C1 N2 H2 119.8(10) . .
C2 N2 H2 116.5(10) . .
C4 N3 C5 117.31(11) . .
C9 N4 C8 117.77(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.2288(15) .
C1 N1 1.3590(16) .
C1 N2 1.3678(16) .
C2 N2 1.4505(17) .
C2 C3 1.5186(17) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.3856(18) .
C3 C7 1.3877(18) .
C4 N3 1.3345(16) .
C4 H4 0.9500 .
C5 N3 1.3484(16) .
C5 C6 1.3903(18) .
C5 C8 1.4886(16) .
C6 C7 1.3799(17) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 N4 1.3506(16) .
C8 C12 1.3876(18) .
C9 N4 1.3351(16) .
C9 C10 1.3932(18) .
C9 H9 0.9500 .
C10 C11 1.3863(17) .
C10 C13 1.5160(16) .
C11 C12 1.3862(17) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 N1 1.4615(17) 3_666
C13 H13A 0.9900 .
C13 H13B 0.9900 .
N1 C13 1.4615(17) 3_666
N1 H1 0.914(17) .
N2 H2 0.875(16) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N4 0.914(17) 2.099(18) 3.0109(15) 175.8(14) 4_575
N2 H2 N3 0.875(16) 2.299(17) 3.0784(16) 148.3(14) 2
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
N2 C2 C3 C4 -163.71(12) .
N2 C2 C3 C7 14.46(18) .
C7 C3 C4 N3 2.5(2) .
C2 C3 C4 N3 -179.19(12) .
N3 C5 C6 C7 3.10(19) .
C8 C5 C6 C7 -178.37(12) .
C5 C6 C7 C3 -1.0(2) .
C4 C3 C7 C6 -1.57(19) .
C2 C3 C7 C6 -179.82(12) .
N3 C5 C8 N4 -155.37(11) .
C6 C5 C8 N4 26.05(17) .
N3 C5 C8 C12 25.69(17) .
C6 C5 C8 C12 -152.89(13) .
N4 C9 C10 C11 -0.77(19) .
N4 C9 C10 C13 176.21(11) .
C9 C10 C11 C12 -0.72(18) .
C13 C10 C11 C12 -177.71(12) .
C10 C11 C12 C8 1.62(19) .
N4 C8 C12 C11 -1.12(19) .
C5 C8 C12 C11 177.76(12) .
C11 C10 C13 N1 90.08(14) 3_666
C9 C10 C13 N1 -86.76(15) 3_666
O1 C1 N1 C13 -12.79(17) 3_666
N2 C1 N1 C13 167.75(10) 3_666
O1 C1 N2 C2 24.65(17) .
N1 C1 N2 C2 -155.88(11) .
C3 C2 N2 C1 61.66(15) .
C3 C4 N3 C5 -0.61(19) .
C6 C5 N3 C4 -2.26(18) .
C8 C5 N3 C4 179.16(11) .
C10 C9 N4 C8 1.29(19) .
C12 C8 N4 C9 -0.31(18) .
C5 C8 N4 C9 -179.25(11) .
