#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:05:52 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179439 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/36/4333693.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_4333693
loop_
_publ_author_name
'Nabanita Sadhukhan'
'Mithun Sarkar'
'Tapas Ghatak'
'S. M. Wahidur Rahaman'
'Leonard J. Barbour'
'Jitendra K. Bera'
_publ_contact_author_address
'Department of Chemistry, IIT Kanpur, Kanpur 208016, INDIA.'
_publ_contact_author_email       jbera@iitk.ac.in
_publ_contact_author_fax         '+ 91-512-2597436'
_publ_contact_author_name        'Jitendra K. Bera'
_publ_contact_author_phone       '+ 91-512-2597336'
_publ_section_title
;
 Reactions of Acids with Naphthyridine-Functionalized Ferrocenes:
 Protonation and Metal Extrusion
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1432
_journal_page_last               1442
_journal_paper_doi               10.1021/ic302155e
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C48 H32 Cl2 Fe4 N10 O14'
_chemical_formula_sum            'C48 H32 Cl2 Fe4 N10 O14'
_chemical_formula_weight         1267.14
_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                98.906(2)
_cell_angle_beta                 106.418(2)
_cell_angle_gamma                101.995(2)
_cell_formula_units_Z            1
_cell_length_a                   10.0600(10)
_cell_length_b                   10.2769(11)
_cell_length_c                   12.5815(13)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.19
_cell_volume                     1188.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10714
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    1.392
_exptl_absorpt_correction_T_max  0.7223
_exptl_absorpt_correction_T_min  0.7051
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_description       Block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0509
_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)+(0.0583P)²+0.3413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                3987
_reflns_number_total             5641
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302155e_si_002_6.cif
_cod_data_source_block           commpond5
_cod_database_code               4333693
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Fe2 Fe 0.71125(5) 0.98324(5) 0.24955(4) 0.02081(14) Uani 1 1 d .
Fe1 Fe 0.62993(5) 0.63138(5) 0.49109(4) 0.02137(14) Uani 1 1 d .
O3 O 0.6283(3) 0.5650(3) 0.3341(2) 0.0245(6) Uani 1 1 d .
O1 O 0.8642(3) 0.6668(2) 0.5181(2) 0.0261(6) Uani 1 1 d .
N2 N 0.6623(3) 0.8705(3) 0.5182(2) 0.0188(6) Uani 1 1 d .
O2 O 1.0680(3) 0.6474(3) 0.5052(2) 0.0279(6) Uani 1 1 d .
N3 N 0.9378(3) 0.6288(3) 0.4610(3) 0.0231(6) Uani 1 1 d .
N1 N 0.7039(3) 0.7567(3) 0.6587(2) 0.0219(6) Uani 1 1 d .
C20 C 0.8713(4) 0.5629(3) 0.3421(3) 0.0205(7) Uani 1 1 d .
C9 C 0.5991(4) 0.9783(3) 0.3615(3) 0.0212(7) Uani 1 1 d .
C5 C 0.7138(3) 0.8814(3) 0.6322(3) 0.0187(7) Uani 1 1 d .
C19 C 0.7196(4) 0.5357(3) 0.2888(3) 0.0216(7) Uani 1 1 d .
C7 C 0.7179(4) 1.1164(4) 0.5619(3) 0.0224(7) Uani 1 1 d .
H7 H 0.7182 1.1974 0.5343 0.027 Uiso 1 1 calc R
C8 C 0.6627(3) 0.9864(3) 0.4834(3) 0.0197(7) Uani 1 1 d .
N4 N 0.5170(3) 0.4318(3) 0.1111(3) 0.0281(7) Uani 1 1 d .
C10 C 0.5416(4) 0.8568(4) 0.2724(3) 0.0233(8) Uani 1 1 d .
H10 H 0.5353 0.7660 0.2820 0.028 Uiso 1 1 calc R
C14 C 0.9275(4) 1.0356(4) 0.3368(3) 0.0247(8) Uani 1 1 d .
H14 H 0.9725 1.0696 0.4166 0.030 Uiso 1 1 calc R
C4 C 0.7693(4) 1.0043(4) 0.7155(3) 0.0222(7) Uani 1 1 d .
O6 O 1.1296(3) 0.4932(3) 0.1496(3) 0.0445(8) Uani 1 1 d .
C12 C 0.5256(4) 1.0397(4) 0.1898(3) 0.0280(8) Uani 1 1 d .
H12 H 0.5056 1.0920 0.1341 0.034 Uiso 1 1 calc R
C6 C 0.7699(4) 1.1252(4) 0.6753(3) 0.0246(8) Uani 1 1 d .
H6 H 0.8064 1.2118 0.7272 0.029 Uiso 1 1 calc R
C3 C 0.8192(4) 0.9944(4) 0.8305(3) 0.0259(8) Uani 1 1 d .
H3 H 0.8603 1.0746 0.8899 0.031 Uiso 1 1 calc R
O5 O 0.4562(3) 0.3123(3) 0.0627(2) 0.0401(7) Uani 1 1 d .
N5 N 1.0025(4) 0.4288(4) 0.1100(3) 0.0353(8) Uani 1 1 d .
O4 O 0.4587(3) 0.5253(3) 0.1106(2) 0.0364(7) Uani 1 1 d .
C24 C 0.6727(4) 0.4656(4) 0.1722(3) 0.0236(8) Uani 1 1 d .
C22 C 0.9060(4) 0.4632(4) 0.1714(3) 0.0278(8) Uani 1 1 d .
O7 O 0.9503(4) 0.3379(3) 0.0235(3) 0.0466(8) Uani 1 1 d .
C13 C 0.5898(4) 1.0929(4) 0.3085(3) 0.0253(8) Uani 1 1 d .
H13 H 0.6212 1.1867 0.3465 0.030 Uiso 1 1 calc R
C21 C 0.9635(4) 0.5294(3) 0.2842(3) 0.0239(8) Uani 1 1 d .
H21 H 1.0642 0.5519 0.3222 0.029 Uiso 1 1 calc R
C18 C 0.8973(4) 1.1155(4) 0.2554(3) 0.0262(8) Uani 1 1 d .
H18 H 0.9179 1.2123 0.2709 0.031 Uiso 1 1 calc R
C1 C 0.7483(4) 0.7513(4) 0.7664(3) 0.0254(8) Uani 1 1 d .
H1 H 0.7397 0.6644 0.7849 0.031 Uiso 1 1 calc R
C16 C 0.8200(4) 0.8896(4) 0.1612(4) 0.0329(10) Uani 1 1 d .
H16 H 0.7803 0.8086 0.1025 0.039 Uiso 1 1 calc R
C11 C 0.4960(4) 0.8954(4) 0.1680(3) 0.0265(8) Uani 1 1 d .
H11 H 0.4526 0.8347 0.0952 0.032 Uiso 1 1 calc R
C2 C 0.8076(4) 0.8687(4) 0.8547(3) 0.0268(8) Uani 1 1 d .
H2 H 0.8397 0.8608 0.9315 0.032 Uiso 1 1 calc R
C15 C 0.8791(4) 0.8961(4) 0.2788(4) 0.0316(9) Uani 1 1 d .
H15 H 0.8852 0.8203 0.3129 0.038 Uiso 1 1 calc R
C17 C 0.8305(4) 1.0249(4) 0.1462(3) 0.0308(9) Uani 1 1 d .
H17 H 0.7987 1.0505 0.0759 0.037 Uiso 1 1 calc R
C23 C 0.7597(4) 0.4277(4) 0.1142(3) 0.0266(8) Uani 1 1 d .
H23 H 0.7209 0.3785 0.0370 0.032 Uiso 1 1 calc R
Cl1 Cl 0.37131(9) 0.57948(9) 0.44372(8) 0.0256(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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C13 Fe2 C17 129.62(16) .
C13 Fe2 C16 168.03(17) .
C17 Fe2 C16 40.73(16) .
C13 Fe2 C10 69.39(15) .
C17 Fe2 C10 147.59(15) .
C16 Fe2 C10 115.49(15) .
C13 Fe2 C9 41.61(14) .
C17 Fe2 C9 169.82(15) .
C16 Fe2 C9 148.81(16) .
C10 Fe2 C9 41.12(13) .
C13 Fe2 C15 150.38(16) .
C17 Fe2 C15 68.43(16) .
C16 Fe2 C15 40.58(16) .
C10 Fe2 C15 108.48(15) .
C9 Fe2 C15 117.02(15) .
C13 Fe2 C12 40.60(15) .
C17 Fe2 C12 107.59(16) .
C16 Fe2 C12 129.29(16) .
C10 Fe2 C12 68.46(15) .
C9 Fe2 C12 68.81(15) .
C15 Fe2 C12 168.11(16) .
C13 Fe2 C18 108.63(15) .
C17 Fe2 C18 40.80(15) .
C16 Fe2 C18 68.43(15) .
C10 Fe2 C18 170.39(15) .
C9 Fe2 C18 131.33(14) .
C15 Fe2 C18 68.29(15) .
C12 Fe2 C18 116.59(16) .
C13 Fe2 C11 68.52(15) .
C17 Fe2 C11 115.44(16) .
C16 Fe2 C11 107.54(16) .
C10 Fe2 C11 40.37(14) .
C9 Fe2 C11 68.48(15) .
C15 Fe2 C11 129.95(16) .
C12 Fe2 C11 40.49(15) .
C18 Fe2 C11 148.55(15) .
C13 Fe2 C14 117.71(15) .
C17 Fe2 C14 68.26(15) .
C16 Fe2 C14 68.15(15) .
C10 Fe2 C14 131.44(15) .
C9 Fe2 C14 109.72(15) .
C15 Fe2 C14 40.53(15) .
C12 Fe2 C14 149.77(15) .
C18 Fe2 C14 40.41(14) .
C11 Fe2 C14 169.24(15) .
O3 Fe1 N1 157.73(11) .
O3 Fe1 O1 78.99(10) .
N1 Fe1 O1 82.86(10) .
O3 Fe1 N2 106.46(10) .
N1 Fe1 N2 59.97(11) .
O1 Fe1 N2 88.44(9) .
O3 Fe1 Cl1 95.60(7) .
N1 Fe1 Cl1 102.70(8) .
O1 Fe1 Cl1 174.45(7) .
N2 Fe1 Cl1 94.36(7) .
O3 Fe1 Cl1 98.71(8) 2_666
N1 Fe1 Cl1 93.91(8) 2_666
O1 Fe1 Cl1 89.54(7) 2_666
N2 Fe1 Cl1 153.85(8) 2_666
Cl1 Fe1 Cl1 90.05(3) 2_666
C19 O3 Fe1 135.7(2) .
N3 O1 Fe1 135.1(2) .
C8 N2 C5 116.8(3) .
C8 N2 Fe1 154.3(2) .
C5 N2 Fe1 88.7(2) .
O2 N3 O1 120.5(3) .
O2 N3 C20 119.2(3) .
O1 N3 C20 120.3(3) .
C1 N1 C5 118.8(3) .
C1 N1 Fe1 141.9(3) .
C5 N1 Fe1 99.0(2) .
C21 C20 C19 123.2(3) .
C21 C20 N3 116.1(3) .
C19 C20 N3 120.7(3) .
C10 C9 C13 107.3(3) .
C10 C9 C8 126.6(3) .
C13 C9 C8 126.1(3) .
C10 C9 Fe2 69.43(19) .
C13 C9 Fe2 69.01(19) .
C8 C9 Fe2 124.4(2) .
N2 C5 N1 112.0(3) .
N2 C5 C4 125.4(3) .
N1 C5 C4 122.6(3) .
O3 C19 C24 119.7(3) .
O3 C19 C20 127.5(3) .
C24 C19 C20 112.8(3) .
C6 C7 C8 120.6(3) .
N2 C8 C7 121.7(3) .
N2 C8 C9 118.4(3) .
C7 C8 C9 119.9(3) .
O5 N4 O4 124.9(3) .
O5 N4 C24 117.3(3) .
O4 N4 C24 117.8(3) .
C11 C10 C9 108.0(3) .
C11 C10 Fe2 70.2(2) .
C9 C10 Fe2 69.45(19) .
C18 C14 C15 108.2(3) .
C18 C14 Fe2 69.6(2) .
C15 C14 Fe2 69.3(2) .
C5 C4 C6 116.1(3) .
C5 C4 C3 117.0(3) .
C6 C4 C3 126.8(3) .
C13 C12 C11 108.5(3) .
C13 C12 Fe2 69.3(2) .
C11 C12 Fe2 69.9(2) .
C7 C6 C4 119.3(3) .
C2 C3 C4 119.3(3) .
O7 N5 O6 125.0(3) .
O7 N5 C22 117.4(4) .
O6 N5 C22 117.6(4) .
C23 C24 C19 125.3(3) .
C23 C24 N4 118.3(3) .
C19 C24 N4 116.3(3) .
C21 C22 C23 121.9(3) .
C21 C22 N5 119.0(3) .
C23 C22 N5 119.1(4) .
C12 C13 C9 107.5(3) .
C12 C13 Fe2 70.1(2) .
C9 C13 Fe2 69.38(19) .
C22 C21 C20 118.8(3) .
C14 C18 C17 107.8(3) .
C14 C18 Fe2 70.0(2) .
C17 C18 Fe2 69.3(2) .
N1 C1 C2 122.5(3) .
C15 C16 C17 108.1(3) .
C15 C16 Fe2 69.8(2) .
C17 C16 Fe2 69.6(2) .
C10 C11 C12 108.6(3) .
C10 C11 Fe2 69.4(2) .
C12 C11 Fe2 69.6(2) .
C3 C2 C1 119.9(4) .
C16 C15 C14 108.0(3) .
C16 C15 Fe2 69.6(2) .
C14 C15 Fe2 70.1(2) .
C16 C17 C18 107.8(4) .
C16 C17 Fe2 69.6(2) .
C18 C17 Fe2 69.9(2) .
C24 C23 C22 117.9(3) .
Fe1 Cl1 Fe1 89.95(3) 2_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe2 C13 2.034(4) .
Fe2 C17 2.038(4) .
Fe2 C16 2.038(4) .
Fe2 C10 2.039(3) .
Fe2 C9 2.039(3) .
Fe2 C15 2.041(4) .
Fe2 C12 2.045(4) .
Fe2 C18 2.047(3) .
Fe2 C11 2.050(4) .
Fe2 C14 2.052(3) .
Fe1 O3 1.982(2) .
Fe1 N1 2.129(3) .
Fe1 O1 2.226(2) .
Fe1 N2 2.368(3) .
Fe1 Cl1 2.4201(10) .
Fe1 Cl1 2.4317(10) 2_666
O3 C19 1.271(4) .
O1 N3 1.245(4) .
N2 C8 1.331(4) .
N2 C5 1.359(4) .
O2 N3 1.230(4) .
N3 C20 1.441(5) .
N1 C1 1.315(5) .
N1 C5 1.364(4) .
C20 C21 1.395(5) .
C20 C19 1.429(5) .
C9 C10 1.432(5) .
C9 C13 1.447(5) .
C9 C8 1.466(5) .
C5 C4 1.404(5) .
C19 C24 1.426(5) .
C7 C6 1.355(5) .
C7 C8 1.429(5) .
N4 O5 1.224(4) .
N4 O4 1.226(4) .
N4 C24 1.475(5) .
C10 C11 1.411(5) .
C14 C18 1.415(5) .
C14 C15 1.418(5) .
C4 C6 1.412(5) .
C4 C3 1.418(5) .
O6 N5 1.228(5) .
C12 C13 1.415(5) .
C12 C11 1.417(5) .
C3 C2 1.362(5) .
N5 O7 1.222(4) .
N5 C22 1.464(5) .
C24 C23 1.366(5) .
C22 C21 1.374(5) .
C22 C23 1.384(5) .
C18 C17 1.424(5) .
C1 C2 1.399(5) .
C16 C15 1.415(6) .
C16 C17 1.418(6) .
Cl1 Fe1 2.4317(10) 2_666
