#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/43/4324379.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_4324379
loop_
_publ_author_name
'Feng Li'
'Jack K. Clegg'
'David Price'
'Cameron J. Kepert'
_publ_section_title
;
 Self-Assembly of a Metallomacrocycle Templated by Iron(II)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              726
_journal_page_last               728
_journal_paper_doi               10.1021/ic102350t
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         '    C28 H22 N8'
_chemical_formula_sum            'C28 H22 N8'
_chemical_formula_weight         470.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 99.149(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.6827(11)
_cell_length_b                   17.030(3)
_cell_length_c                   12.229(3)
_cell_measurement_reflns_used    3769
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.022
_cell_measurement_theta_min      2.923
_cell_volume                     1168.4(4)
_computing_cell_refinement       'SAINT (Bruker-Nonius, 2003)'
_computing_data_collection       'APEX (Bruker-Nonius, 2003)'
_computing_data_reduction
'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)'
_computing_molecular_graphics
;ORTEP-3 (Farrugia, 1997)
WINGX-32 (Farrugia, 1999) 
;
_computing_publication_material  'enCIFer 1.1 (CCDC, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  APEXII-FR591
_diffrn_measurement_method       ω+φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11963
_diffrn_reflns_theta_full        29.15
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         3.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0432
_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)+(0.0531P)²+0.2335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                2345
_reflns_number_total             3128
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic102350t_si_002_1.cif
_cod_data_source_block           fl109
_cod_original_formula_sum        '    C28 H22 N8'
_cod_database_code               4324379
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 0.0115(2) 0.38779(7) 0.45206(9) 0.0297(3) Uani 1 1 d .
C2 C -0.2165(3) 0.44142(9) 0.29792(11) 0.0435(3) Uani 1 1 d .
H2 H -0.3637 0.4441 0.2488 0.052 Uiso 1 1 calc R
C3 C -0.0343(3) 0.49043(8) 0.27782(11) 0.0436(3) Uani 1 1 d .
H3 H -0.0558 0.5255 0.2166 0.052 Uiso 1 1 calc R
C4 C 0.1812(3) 0.48710(8) 0.34959(11) 0.0414(3) Uani 1 1 d .
H4 H 0.3103 0.5200 0.3382 0.050 Uiso 1 1 calc R
C5 C 0.2053(2) 0.43524(7) 0.43783(11) 0.0343(3) Uani 1 1 d .
H5 H 0.3510 0.4319 0.4879 0.041 Uiso 1 1 calc R
C6 C 0.0272(2) 0.33175(7) 0.54482(10) 0.0296(3) Uani 1 1 d .
C7 C -0.0421(2) 0.24246(8) 0.66632(12) 0.0403(3) Uani 1 1 d .
H7 H -0.1138 0.2044 0.7074 0.048 Uiso 1 1 calc R
C8 C -0.1522(2) 0.28274(8) 0.57469(11) 0.0383(3) Uani 1 1 d .
H8 H -0.3132 0.2785 0.5394 0.046 Uiso 1 1 calc R
C9 C 0.3671(2) 0.24995(8) 0.78425(12) 0.0428(3) Uani 1 1 d .
H9A H 0.5183 0.2344 0.7598 0.051 Uiso 1 1 calc R
H9B H 0.3127 0.2057 0.8264 0.051 Uiso 1 1 calc R
C10 C 0.4081(2) 0.32151(8) 0.85772(11) 0.0377(3) Uani 1 1 d .
C11 C 0.5917(2) 0.37405(9) 0.84629(11) 0.0413(3) Uani 1 1 d .
H11 H 0.6973 0.3604 0.7964 0.050 Uiso 1 1 calc R
C12 C 0.4801(2) 0.46119(8) 0.97207(10) 0.0368(3) Uani 1 1 d .
C13 C 0.2953(2) 0.41118(9) 0.99180(11) 0.0406(3) Uani 1 1 d .
H13 H 0.1957 0.4251 1.0442 0.049 Uiso 1 1 calc R
C14 C 0.2602(2) 0.34135(9) 0.93385(12) 0.0414(3) Uani 1 1 d .
H14 H 0.1352 0.3070 0.9460 0.050 Uiso 1 1 calc R
N1 N -0.19847(18) 0.39010(7) 0.38278(9) 0.0377(3) Uani 1 1 d .
N2 N 0.23401(17) 0.32236(6) 0.61400(9) 0.0336(2) Uani 1 1 d .
N3 N 0.18671(18) 0.26703(6) 0.68712(9) 0.0355(3) Uani 1 1 d .
N4 N 0.62891(19) 0.44207(7) 0.90075(9) 0.0412(3) 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'
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_3
N1 C1 C5 122.68(11) .
N1 C1 C6 116.19(11) .
C5 C1 C6 121.12(11) .
N1 C2 C3 124.14(13) .
N1 C2 H2 117.9 .
C3 C2 H2 117.9 .
C2 C3 C4 118.22(13) .
C2 C3 H3 120.9 .
C4 C3 H3 120.9 .
C5 C4 C3 119.09(13) .
C5 C4 H4 120.5 .
C3 C4 H4 120.5 .
C4 C5 C1 118.90(12) .
C4 C5 H5 120.6 .
C1 C5 H5 120.6 .
N2 C6 C8 111.26(11) .
N2 C6 C1 120.09(10) .
C8 C6 C1 128.65(11) .
N3 C7 C8 107.36(11) .
N3 C7 H7 126.3 .
C8 C7 H7 126.3 .
C7 C8 C6 104.58(11) .
C7 C8 H8 127.7 .
C6 C8 H8 127.7 .
N3 C9 C10 110.06(10) .
N3 C9 H9A 109.6 .
C10 C9 H9A 109.6 .
N3 C9 H9B 109.6 .
C10 C9 H9B 109.6 .
H9A C9 H9B 108.2 .
C14 C10 C11 116.82(14) .
C14 C10 C9 122.78(12) .
C11 C10 C9 120.28(12) .
N4 C11 C10 124.50(13) .
N4 C11 H11 117.8 .
C10 C11 H11 117.8 .
N4 C12 C13 121.92(13) .
N4 C12 C12 116.49(13) 3_667
C13 C12 C12 121.58(15) 3_667
C14 C13 C12 119.02(13) .
C14 C13 H13 120.5 .
C12 C13 H13 120.5 .
C13 C14 C10 119.90(12) .
C13 C14 H14 120.0 .
C10 C14 H14 120.0 .
C2 N1 C1 116.97(11) .
C6 N2 N3 104.64(10) .
C7 N3 N2 112.15(11) .
C7 N3 C9 128.14(11) .
N2 N3 C9 119.02(10) .
C11 N4 C12 117.78(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.3495(15) .
C1 C5 1.3990(17) .
C1 C6 1.4743(17) .
C2 N1 1.3481(18) .
C2 C3 1.382(2) .
C2 H2 0.9500 .
C3 C4 1.390(2) .
C3 H3 0.9500 .
C4 C5 1.3843(18) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C6 N2 1.3438(15) .
C6 C8 1.4101(17) .
C7 N3 1.3510(16) .
C7 C8 1.376(2) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 N3 1.4694(17) .
C9 C10 1.510(2) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C14 1.392(2) .
C10 C11 1.3983(18) .
C11 N4 1.3362(19) .
C11 H11 0.9500 .
C12 N4 1.3478(17) .
C12 C13 1.4026(17) .
C12 C12 1.489(3) 3_667
C13 C14 1.382(2) .
C13 H13 0.9500 .
C14 H14 0.9500 .
N2 N3 1.3550(14) .
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_1
N1 C2 C3 C4 -0.3(2) .
C2 C3 C4 C5 0.0(2) .
C3 C4 C5 C1 -0.06(19) .
N1 C1 C5 C4 0.38(18) .
C6 C1 C5 C4 -179.80(11) .
N1 C1 C6 N2 176.14(10) .
C5 C1 C6 N2 -3.69(17) .
N1 C1 C6 C8 -3.67(18) .
C5 C1 C6 C8 176.51(12) .
N3 C7 C8 C6 -0.13(14) .
N2 C6 C8 C7 -0.24(14) .
C1 C6 C8 C7 179.58(11) .
N3 C9 C10 C14 81.92(14) .
N3 C9 C10 C11 -93.90(14) .
C14 C10 C11 N4 -1.99(19) .
C9 C10 C11 N4 174.07(12) .
N4 C12 C13 C14 -2.04(18) .
C12 C12 C13 C14 177.14(13) 3_667
C12 C13 C14 C10 0.33(19) .
C11 C10 C14 C13 1.54(18) .
C9 C10 C14 C13 -174.41(12) .
C3 C2 N1 C1 0.6(2) .
C5 C1 N1 C2 -0.62(17) .
C6 C1 N1 C2 179.56(11) .
C8 C6 N2 N3 0.50(13) .
C1 C6 N2 N3 -179.33(10) .
C8 C7 N3 N2 0.46(15) .
C8 C7 N3 C9 170.77(12) .
C6 N2 N3 C7 -0.60(13) .
C6 N2 N3 C9 -171.88(11) .
C10 C9 N3 C7 -105.96(15) .
C10 C9 N3 N2 63.76(15) .
C10 C11 N4 C12 0.39(19) .
C13 C12 N4 C11 1.67(18) .
C12 C12 N4 C11 -177.55(13) 3_667
