#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:24:16 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179139 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/00/4310044.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_4310044
loop_
_publ_author_name
'Nicolas Bréfuel'
'Christine Lepetit'
'Sergiu Shova'
'Françoise Dahan'
'Jean-Pierre Tuchagues'
_publ_section_title
;
Complexation to FeII, NiII, and ZnII of Multidentate Ligands Resulting from
Condensation of 2-Pyridinecarboxaldehyde with α,ω-Triamines: Selective
Imidazolidine/Hexahydropyrimidine Ring Opening Revisited
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8916
_journal_page_last               8928
_journal_paper_doi               10.1021/ic050791b
_journal_volume                  44
_journal_year                    2005
_chemical_formula_moiety         'C18 H19 Fe N7 S2'
_chemical_formula_sum            'C18 H19 Fe N7 S2'
_chemical_formula_weight         453.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 112.213(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5853(17)
_cell_length_b                   13.1522(10)
_cell_length_c                   13.0116(15)
_cell_measurement_reflns_used    7998
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      51.9
_cell_measurement_theta_min      6.1
_cell_volume                     2152.3(4)
_computing_cell_refinement       'STOE-IPDS software (Stoe, 2.93, 1997)'
_computing_data_collection       'STOE-IPDS software (Stoe, 2.93, 1997)'
_computing_data_reduction        'XRED (Stoe, 1.08, 1996)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  STOE-IPDS
_diffrn_measurement_method       'Imaging Plate Detector System'
_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  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9389
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         4.34
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  0.8386
_exptl_absorpt_correction_T_min  0.7116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'c.f. r.h. blessing, acta cryst. (1995), a51, 33-38'
_exptl_crystal_colour            Dark-Red
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3879
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0244
_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)+(0.0485P)²+0.8663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0683
_reflns_number_gt                3830
_reflns_number_total             3879
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic050791bsi20050517_045858.cif
_cod_data_source_block           FeLA(NCS)2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4310044
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.153659(15) 0.655125(17) 0.356410(16) 0.02081(9) Uani 1 1 d . . .
N1 N 0.18149(15) 0.67162(13) 0.21904(17) 0.0281(4) Uani 1 1 d . . .
N2 N 0.02985(14) 0.72716(12) 0.27153(15) 0.0260(4) Uani 1 1 d . . .
N3 N 0.09391(13) 0.66219(12) 0.47842(15) 0.0214(4) Uani 1 1 d . . .
N5 N 0.22717(13) 0.78039(12) 0.42630(14) 0.0235(3) Uani 1 1 d . . .
C1 C 0.2663(2) 0.64309(17) 0.1965(2) 0.0338(5) Uani 1 1 d . . .
H1 H 0.3228 0.6083 0.2521 0.037 Uiso 1 1 calc R . .
C2 C 0.2745(2) 0.66264(18) 0.0949(2) 0.0414(6) Uani 1 1 d . . .
H2 H 0.3358 0.6418 0.0820 0.045 Uiso 1 1 calc R . .
C3 C 0.1929(3) 0.7124(2) 0.0131(2) 0.0475(6) Uani 1 1 d . . .
H3 H 0.1973 0.7262 -0.0567 0.052 Uiso 1 1 calc R . .
C4 C 0.1049(2) 0.7421(2) 0.0338(2) 0.0442(6) Uani 1 1 d . . .
H4 H 0.0474 0.7759 -0.0217 0.049 Uiso 1 1 calc R . .
C5 C 0.10166(19) 0.72160(17) 0.1372(2) 0.0337(5) Uani 1 1 d . . .
C6 C 0.01503(18) 0.75088(17) 0.1719(2) 0.0329(5) Uani 1 1 d . . .
H6 H -0.0472 0.7848 0.1241 0.036 Uiso 1 1 calc R . .
C7 C -0.04457(15) 0.75086(16) 0.32540(19) 0.0292(4) Uani 1 1 d . . .
H7A H -0.1189 0.7465 0.2714 0.032 Uiso 1 1 calc R . .
H7B H -0.0317 0.8203 0.3572 0.032 Uiso 1 1 calc R . .
C8 C -0.02399(15) 0.67172(16) 0.41699(19) 0.0262(4) Uani 1 1 d . . .
H8A H -0.0582 0.6930 0.4686 0.029 Uiso 1 1 calc R . .
H8B H -0.0543 0.6054 0.3843 0.029 Uiso 1 1 calc R . .
C9 C 0.12106(16) 0.57282(15) 0.55621(18) 0.0248(4) Uani 1 1 d . . .
H9A H 0.1419 0.5132 0.5226 0.027 Uiso 1 1 calc R . .
H9B H 0.0604 0.5540 0.5768 0.027 Uiso 1 1 calc R . .
C10 C 0.21424(16) 0.61161(16) 0.65645(18) 0.0289(4) Uani 1 1 d . . .
H10A H 0.2217 0.5723 0.7238 0.032 Uiso 1 1 calc R . .
H10B H 0.2815 0.6070 0.6437 0.032 Uiso 1 1 calc R . .
N4 N 0.18691(15) 0.71830(14) 0.66744(16) 0.0282(4) Uani 1 1 d D . .
H4A H 0.148(3) 0.723(3) 0.704(3) 0.063(11) Uiso 1 1 d D . .
C11 C 0.13565(15) 0.75431(14) 0.55373(17) 0.0235(4) Uani 1 1 d . . .
H11 H 0.0745 0.7991 0.5485 0.026 Uiso 1 1 calc R . .
C12 C 0.21134(15) 0.81314(15) 0.51670(18) 0.0249(4) Uani 1 1 d . . .
C13 C 0.26143(18) 0.89956(17) 0.5742(2) 0.0333(5) Uani 1 1 d . . .
H13 H 0.2485 0.9217 0.6374 0.037 Uiso 1 1 calc R . .
C14 C 0.3304(2) 0.95326(18) 0.5386(2) 0.0415(6) Uani 1 1 d . . .
H14 H 0.3639 1.0135 0.5757 0.046 Uiso 1 1 calc R . .
C15 C 0.3493(2) 0.91750(19) 0.4484(2) 0.0423(6) Uani 1 1 d . . .
H15 H 0.3984 0.9514 0.4242 0.046 Uiso 1 1 calc R . .
C16 C 0.29609(19) 0.83161(17) 0.3929(2) 0.0331(5) Uani 1 1 d . . .
H16 H 0.3085 0.8082 0.3298 0.036 Uiso 1 1 calc R . .
N6 N 0.08135(14) 0.52521(13) 0.30523(16) 0.0266(4) Uani 1 1 d . . .
C17 C 0.03660(15) 0.44841(14) 0.27935(16) 0.0227(4) Uani 1 1 d . . .
S1 S -0.02844(4) 0.34099(4) 0.23953(5) 0.02978(13) Uani 1 1 d . . .
N7 N 0.28577(14) 0.58165(13) 0.43618(16) 0.0284(4) Uani 1 1 d . . .
C18 C 0.36851(18) 0.54346(16) 0.4744(2) 0.0358(5) Uani 1 1 d . . .
S2 S 0.4851(3) 0.4924(3) 0.5100(3) 0.0535(8) Uani 0.55 1 d PU . .
S2' S 0.4867(4) 0.4908(4) 0.5549(3) 0.0603(11) Uani 0.45 1 d PU . .
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'
S S 0.1246 0.1234 '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
N2 Fe N7 176.01(8) . . ?
N2 Fe N6 91.00(7) . . ?
N7 Fe N6 89.49(7) . . ?
N2 Fe N5 91.99(7) . . ?
N7 Fe N5 87.98(7) . . ?
N6 Fe N5 172.82(8) . . ?
N2 Fe N1 81.25(8) . . ?
N7 Fe N1 94.78(8) . . ?
N6 Fe N1 91.79(7) . . ?
N5 Fe N1 95.12(7) . . ?
N2 Fe N3 84.46(8) . . ?
N7 Fe N3 99.49(7) . . ?
N6 Fe N3 90.48(7) . . ?
N5 Fe N3 83.32(7) . . ?
N1 Fe N3 165.57(7) . . ?
C1 N1 C5 117.2(2) . . ?
C1 N1 Fe 129.75(19) . . ?
C5 N1 Fe 113.03(16) . . ?
C6 N2 C7 124.25(19) . . ?
C6 N2 Fe 118.90(16) . . ?
C7 N2 Fe 116.85(14) . . ?
C8 N3 C9 111.39(15) . . ?
C8 N3 C11 109.77(15) . . ?
C9 N3 C11 104.55(16) . . ?
C8 N3 Fe 104.35(13) . . ?
C9 N3 Fe 114.82(12) . . ?
C11 N3 Fe 112.04(12) . . ?
C12 N5 C16 118.76(18) . . ?
C12 N5 Fe 116.92(13) . . ?
C16 N5 Fe 124.22(16) . . ?
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.8(2) . . ?
N1 C5 C6 112.3(2) . . ?
C4 C5 C6 124.9(2) . . ?
N2 C6 C5 114.5(2) . . ?
N2 C6 H6 122.8 . . ?
C5 C6 H6 122.8 . . ?
N2 C7 C8 105.82(16) . . ?
N2 C7 H7A 110.6 . . ?
C8 C7 H7A 110.6 . . ?
N2 C7 H7B 110.6 . . ?
C8 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
N3 C8 C7 108.45(16) . . ?
N3 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
N3 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N3 C9 C10 103.17(16) . . ?
N3 C9 H9A 111.1 . . ?
C10 C9 H9A 111.1 . . ?
N3 C9 H9B 111.1 . . ?
C10 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
N4 C10 C9 104.13(16) . . ?
N4 C10 H10A 110.9 . . ?
C9 C10 H10A 110.9 . . ?
N4 C10 H10B 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C11 N4 C10 104.64(16) . . ?
C11 N4 H4A 113(3) . . ?
C10 N4 H4A 111(3) . . ?
N4 C11 C12 111.75(16) . . ?
N4 C11 N3 108.25(16) . . ?
C12 C11 N3 109.61(16) . . ?
N4 C11 H11 109.1 . . ?
C12 C11 H11 109.1 . . ?
N3 C11 H11 109.1 . . ?
N5 C12 C13 121.70(19) . . ?
N5 C12 C11 118.06(17) . . ?
C13 C12 C11 120.2(2) . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N5 C16 C15 121.8(2) . . ?
N5 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C17 N6 Fe 176.46(16) . . ?
N6 C17 S1 178.52(19) . . ?
C18 N7 Fe 171.76(19) . . ?
N7 C18 S2 171.5(3) . . ?
N7 C18 S2' 168.6(3) . . ?
S2 C18 S2' 19.86(17) . . ?
S2' S2 C18 87.9(8) . . ?
S2 S2' C18 72.2(8) . . ?
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 N2 1.8820(18) . ?
Fe N7 1.9554(18) . ?
Fe N6 1.9579(17) . ?
Fe N5 1.9627(16) . ?
Fe N1 1.974(2) . ?
Fe N3 2.0401(19) . ?
N1 C1 1.345(3) . ?
N1 C5 1.367(3) . ?
N2 C6 1.273(3) . ?
N2 C7 1.465(3) . ?
N3 C8 1.501(2) . ?
N3 C9 1.503(2) . ?
N3 C11 1.526(2) . ?
N5 C12 1.344(3) . ?
N5 C16 1.352(3) . ?
C1 C2 1.393(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.463(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.526(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N4 1.472(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N4 C11 1.456(3) . ?
N4 H4A 0.836(18) . ?
C11 C12 1.504(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.389(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N6 C17 1.161(3) . ?
C17 S1 1.6428(19) . ?
N7 C18 1.158(3) . ?
C18 S2 1.618(4) . ?
C18 S2' 1.698(5) . ?
S2 S2' 0.577(5) . ?
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
N4 H4A S1 0.836(18) 2.74(3) 3.482(2) 149(3) 2_565
