#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:13:32 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179051 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/13/4301398.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_4301398
loop_
_publ_author_name
'Benjamin J. Coe'
'Simon P. Foxon'
'Elizabeth C. Harper'
'James Raftery'
'Rachel Shaw'
'Catherine A. Swanson'
'Inge Asselberghs'
'Koen Clays'
'Bruce S. Brunschwig'
'Anthony G. Fitch'
_publ_section_title
;
Nonlinear Optical and Related Properties of Iron(II) Pentacyanide Complexes
with Quaternary Nitrogen Electron Acceptor Units
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1370
_journal_page_last               1379
_journal_paper_doi               10.1021/ic801224u
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C15 H20 Fe N9 Na O3'
_chemical_formula_weight         453.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           26
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2'
_symmetry_space_group_name_H-M   'P m c 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.6975(3)
_cell_length_b                   7.9969(3)
_cell_length_c                   15.8435(6)
_cell_measurement_reflns_used    1854
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.714
_cell_measurement_theta_min      2.482
_cell_volume                     975.26(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       'w\ rotation wuth narrow frames'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS STATION 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.69260
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10119
_diffrn_reflns_theta_full        31.04
_diffrn_reflns_theta_max         31.04
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_correction_T_min  0.8852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.088(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         3262
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0372
_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)+(0.0652P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                3177
_reflns_number_total             3262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801224u_si_001_2.cif
_cod_data_source_block           1P.3H2O
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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               4301398
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, 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
Fe1 Fe 0.0000 0.21915(4) 0.217544(19) 0.01489(10) Uani 1 2 d S . .
Na1 Na 0.5000 0.16634(15) 0.44612(7) 0.0236(2) Uani 1 2 d S . .
O1 O 0.5000 -0.0895(3) 0.52647(14) 0.0306(4) Uani 1 2 d S . .
O2 O 0.7219(3) 0.2919(2) 0.52807(13) 0.0364(4) Uani 1 1 d . . .
N1 N 0.0000 -0.1064(3) 0.11426(16) 0.0303(5) Uani 1 2 d S . .
N2 N 0.2815(2) 0.0787(2) 0.33757(11) 0.0269(3) Uani 1 1 d . . .
N3 N 0.2627(2) 0.3678(2) 0.09143(11) 0.0265(3) Uani 1 1 d . . .
N4 N 0.0000 0.4209(2) 0.28781(12) 0.0160(3) Uani 1 2 d S . .
N5 N 0.0000 0.7014(3) 0.39139(14) 0.0192(4) Uani 1 2 d S . .
N6 N 0.5000 0.4409(3) 0.35915(17) 0.0303(5) Uani 1 2 d S . .
N7 N 0.5000 0.7142(3) 0.25354(16) 0.0245(5) Uani 1 2 d S . .
C1 C 0.0000 0.0182(3) 0.15297(16) 0.0211(4) Uani 1 2 d S . .
C2 C 0.1780(2) 0.1268(2) 0.29037(11) 0.0198(3) Uani 1 1 d . . .
C3 C 0.1698(2) 0.3113(2) 0.14152(11) 0.0194(3) Uani 1 1 d . . .
C4 C 0.0000 0.4092(3) 0.37321(15) 0.0212(4) Uani 1 2 d S . .
H4 H 0.0000 0.3013 0.3983 0.025 Uiso 1 2 calc SR . .
C5 C 0.0000 0.5476(3) 0.42503(15) 0.0205(4) Uani 1 2 d S . .
H5 H 0.0000 0.5340 0.4846 0.025 Uiso 1 2 calc SR . .
C6 C 0.0000 0.5781(3) 0.25654(15) 0.0205(4) Uani 1 2 d S . .
H6 H 0.0000 0.5921 0.1970 0.025 Uiso 1 2 calc SR . .
C7 C 0.0000 0.7191(3) 0.30657(18) 0.0228(5) Uani 1 2 d S . .
H7 H 0.0000 0.8273 0.2818 0.027 Uiso 1 2 calc SR . .
C8 C 0.0000 0.8498(3) 0.44745(16) 0.0259(5) Uani 1 2 d S . .
H8A H 0.0375 0.8168 0.5042 0.039 Uiso 0.50 1 calc PR . .
H8B H -0.1175 0.8967 0.4502 0.039 Uiso 0.50 1 calc PR . .
H8C H 0.0800 0.9341 0.4250 0.039 Uiso 0.50 1 calc PR . .
C9 C 0.5000 0.4237(4) 0.2762(2) 0.0296(6) Uani 1 2 d S . .
H9 H 0.5000 0.3142 0.2529 0.036 Uiso 1 2 calc SR . .
C10 C 0.5000 0.5602(3) 0.2218(2) 0.0250(4) Uani 1 2 d S . .
H10 H 0.5000 0.5435 0.1624 0.030 Uiso 1 2 calc SR . .
C11 C 0.5000 0.5965(4) 0.3892(2) 0.0343(7) Uani 1 2 d S . .
H11 H 0.5000 0.6121 0.4486 0.041 Uiso 1 2 calc SR . .
C12 C 0.5000 0.7374(4) 0.3375(2) 0.0334(7) Uani 1 2 d S . .
H12 H 0.5000 0.8467 0.3609 0.040 Uiso 1 2 calc SR . .
C13 C 0.5000 0.8629(4) 0.19529(18) 0.0295(6) Uani 1 2 d S . .
H13A H 0.3805 0.8884 0.1783 0.044 Uiso 0.50 1 calc PR . .
H13B H 0.5696 0.8374 0.1451 0.044 Uiso 0.50 1 calc PR . .
H13C H 0.5499 0.9596 0.2245 0.044 Uiso 0.50 1 calc PR . .
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'
Na Na 0.0362 0.0249 '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'
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
_geom_angle_publ_flag
C1 Fe1 C3 89.24(8) . 3 ?
C1 Fe1 C3 89.24(8) . . ?
C3 Fe1 C3 85.60(11) 3 . ?
C1 Fe1 C2 89.90(7) . . ?
C3 Fe1 C2 177.63(8) 3 . ?
C3 Fe1 C2 92.19(7) . . ?
C1 Fe1 C2 89.90(7) . 3 ?
C3 Fe1 C2 92.19(7) 3 3 ?
C3 Fe1 C2 177.63(8) . 3 ?
C2 Fe1 C2 90.02(10) . 3 ?
C1 Fe1 N4 177.86(10) . . ?
C3 Fe1 N4 92.32(7) 3 . ?
C3 Fe1 N4 92.32(7) . . ?
C2 Fe1 N4 88.59(7) . . ?
C2 Fe1 N4 88.59(7) 3 . ?
O2 Na1 O2 92.28(11) . 3_655 ?
O2 Na1 O1 94.03(6) . . ?
O2 Na1 O1 94.03(6) 3_655 . ?
O2 Na1 N2 168.19(8) . . ?
O2 Na1 N2 90.61(7) 3_655 . ?
O1 Na1 N2 97.19(7) . . ?
O2 Na1 N2 90.61(7) . 3_655 ?
O2 Na1 N2 168.19(8) 3_655 3_655 ?
O1 Na1 N2 97.19(7) . 3_655 ?
N2 Na1 N2 84.34(9) . 3_655 ?
O2 Na1 N6 86.13(7) . . ?
O2 Na1 N6 86.13(7) 3_655 . ?
O1 Na1 N6 179.77(10) . . ?
N2 Na1 N6 82.64(7) . . ?
N2 Na1 N6 82.65(7) 3_655 . ?
C2 N2 Na1 144.28(15) . . ?
C6 N4 C4 115.5(2) . . ?
C6 N4 Fe1 123.88(17) . . ?
C4 N4 Fe1 120.66(16) . . ?
C5 N5 C7 119.5(2) . . ?
C5 N5 C8 119.8(2) . . ?
C7 N5 C8 120.8(2) . . ?
C9 N6 C11 116.9(3) . . ?
C9 N6 Na1 116.1(2) . . ?
C11 N6 Na1 127.0(2) . . ?
C10 N7 C12 120.1(3) . . ?
C10 N7 C13 120.0(2) . . ?
C12 N7 C13 119.9(2) . . ?
N1 C1 Fe1 179.1(2) . . ?
N2 C2 Fe1 175.83(17) . . ?
N3 C3 Fe1 175.06(16) . . ?
N4 C4 C5 122.6(2) . . ?
N4 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
N5 C5 C4 120.0(2) . . ?
N5 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N4 C6 C7 123.4(2) . . ?
N4 C6 H6 118.3 . . ?
C7 C6 H6 118.3 . . ?
N5 C7 C6 119.1(2) . . ?
N5 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N6 C9 C10 122.3(3) . . ?
N6 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
N7 C10 C9 119.5(3) . . ?
N7 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N6 C11 C12 123.1(3) . . ?
N6 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
N7 C12 C11 118.1(3) . . ?
N7 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
N7 C13 H13A 109.5 . . ?
N7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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
Fe1 C1 1.905(3) . ?
Fe1 C3 1.9242(19) 3 ?
Fe1 C3 1.9242(19) . ?
Fe1 C2 1.9377(18) . ?
Fe1 C2 1.9377(18) 3 ?
Fe1 N4 1.960(2) . ?
Na1 O2 2.369(2) . ?
Na1 O2 2.369(2) 3_655 ?
Na1 O1 2.410(2) . ?
Na1 N2 2.5057(19) . ?
Na1 N2 2.5057(19) 3_655 ?
Na1 N6 2.592(3) . ?
N1 C1 1.170(4) . ?
N2 C2 1.158(2) . ?
N3 C3 1.160(2) . ?
N4 C6 1.351(3) . ?
N4 C4 1.356(3) . ?
N5 C5 1.340(3) . ?
N5 C7 1.351(4) . ?
N5 C8 1.483(3) . ?
N6 C9 1.321(4) . ?
N6 C11 1.333(4) . ?
N7 C10 1.331(3) . ?
N7 C12 1.343(4) . ?
N7 C13 1.505(4) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.379(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.393(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Na1 N2 C2 -44.1(5) . . . . ?
O2 Na1 N2 C2 60.1(3) 3_655 . . . ?
O1 Na1 N2 C2 154.2(3) . . . . ?
N2 Na1 N2 C2 -109.2(2) 3_655 . . . ?
N6 Na1 N2 C2 -25.9(3) . . . . ?
C1 Fe1 N4 C6 180.000(6) . . . . ?
C3 Fe1 N4 C6 -42.84(5) 3 . . . ?
C3 Fe1 N4 C6 42.84(5) . . . . ?
C2 Fe1 N4 C6 134.97(5) . . . . ?
C2 Fe1 N4 C6 -134.97(5) 3 . . . ?
C1 Fe1 N4 C4 0.000(6) . . . . ?
C3 Fe1 N4 C4 137.16(5) 3 . . . ?
C3 Fe1 N4 C4 -137.16(5) . . . . ?
C2 Fe1 N4 C4 -45.03(5) . . . . ?
C2 Fe1 N4 C4 45.03(5) 3 . . . ?
O2 Na1 N6 C9 133.72(5) . . . . ?
O2 Na1 N6 C9 -133.72(5) 3_655 . . . ?
O1 Na1 N6 C9 0.00(9) . . . . ?
N2 Na1 N6 C9 -42.60(4) . . . . ?
N2 Na1 N6 C9 42.60(4) 3_655 . . . ?
O2 Na1 N6 C11 -46.28(5) . . . . ?
O2 Na1 N6 C11 46.28(5) 3_655 . . . ?
O1 Na1 N6 C11 180.00(9) . . . . ?
N2 Na1 N6 C11 137.40(4) . . . . ?
N2 Na1 N6 C11 -137.40(4) 3_655 . . . ?
C3 Fe1 C1 N1 -137.20(6) 3 . . . ?
C3 Fe1 C1 N1 137.20(6) . . . . ?
C2 Fe1 C1 N1 45.01(5) . . . . ?
C2 Fe1 C1 N1 -45.01(5) 3 . . . ?
N4 Fe1 C1 N1 0.000(17) . . . . ?
Na1 N2 C2 Fe1 -40(2) . . . . ?
C1 Fe1 C2 N2 -160(2) . . . . ?
C3 Fe1 C2 N2 132(2) 3 . . . ?
C3 Fe1 C2 N2 111(2) . . . . ?
C2 Fe1 C2 N2 -70(2) 3 . . . ?
N4 Fe1 C2 N2 19(2) . . . . ?
C1 Fe1 C3 N3 73(2) . . . . ?
C3 Fe1 C3 N3 -17(2) 3 . . . ?
C2 Fe1 C3 N3 163(2) . . . . ?
C2 Fe1 C3 N3 4(4) 3 . . . ?
N4 Fe1 C3 N3 -109(2) . . . . ?
C6 N4 C4 C5 0.0 . . . . ?
Fe1 N4 C4 C5 180.0 . . . . ?
C7 N5 C5 C4 0.000(1) . . . . ?
C8 N5 C5 C4 180.0 . . . . ?
N4 C4 C5 N5 0.0 . . . . ?
C4 N4 C6 C7 0.0 . . . . ?
Fe1 N4 C6 C7 180.0 . . . . ?
C5 N5 C7 C6 0.0 . . . . ?
C8 N5 C7 C6 180.0 . . . . ?
N4 C6 C7 N5 0.0 . . . . ?
C11 N6 C9 C10 0.000(1) . . . . ?
Na1 N6 C9 C10 180.0 . . . . ?
C12 N7 C10 C9 0.0 . . . . ?
C13 N7 C10 C9 180.0 . . . . ?
N6 C9 C10 N7 0.0 . . . . ?
C9 N6 C11 C12 0.000(1) . . . . ?
Na1 N6 C11 C12 180.0 . . . . ?
C10 N7 C12 C11 0.000(1) . . . . ?
C13 N7 C12 C11 180.0 . . . . ?
N6 C11 C12 N7 0.000(1) . . . . ?
