#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/56/2015642.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015642
loop_
_publ_author_name
'Yao-Cheng Shi'
'Bei-Bei Zhu'
'Xiao-Bi Jing'
_publ_section_title
;
 N,N'-Bis(2-pyridylmethyl)ferrocene-1,1'-diyldicarboxamide
 and
 N,N'-bis(3-pyridylmethyl)ferrocene-1,1'-diyldicarboxamide
;
_journal_coeditor_code           GD3052
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m559
_journal_page_last               m562
_journal_paper_doi               10.1107/S0108270106041345
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Fe (C12 H11 N2 O1)2]'
_chemical_formula_moiety         'C24 H22 Fe N4 O2'
_chemical_formula_sum            'C24 H22 Fe N4 O2'
_chemical_formula_weight         454.31
_chemical_name_systematic
;
N,N'-Bis(2-pyridylmethyl)ferrocene-1,1'-diyldicarboxamide
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_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                100.297(2)
_cell_angle_beta                 102.114(2)
_cell_angle_gamma                114.0510(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9859(2)
_cell_length_b                   9.8987(2)
_cell_length_c                   13.7459(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      15
_cell_measurement_theta_min      9
_cell_volume                     1042.75(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'OSCAIL-X and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL-X (McArdle, 2005) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14739
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ψ scan (North et al.,  1968)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.404
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0348P)²+0.4231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3611
_reflns_number_total             4769
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3052.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical'
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 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2015642
_cod_database_fobs_code          2015642
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.4562(3) 0.2882(3) 0.05827(18) 0.0443(6) Uani d . 1
H H1 0.5169 0.3719 0.0306 0.053 Uiso calc R 1
C C2 0.5007(4) 0.1708(3) 0.0753(2) 0.0502(7) Uani d . 1
H H2 0.5992 0.1603 0.0624 0.060 Uiso calc R 1
C C3 0.3808(4) 0.0723(3) 0.1160(2) 0.0502(7) Uani d . 1
H H3 0.3821 -0.0177 0.1357 0.060 Uiso calc R 1
C C4 0.2607(3) 0.1278(3) 0.12431(19) 0.0432(6) Uani d . 1
H H4 0.1637 0.0827 0.1505 0.052 Uiso calc R 1
C C5 0.3059(3) 0.2622(3) 0.08875(17) 0.0378(6) Uani d . 1
C C6 0.2204(3) 0.3619(3) 0.08464(18) 0.0396(6) Uani d . 1
C C7 -0.0035(4) 0.4176(3) 0.1251(2) 0.0468(6) Uani d . 1
H H7A -0.1109 0.3594 0.1374 0.056 Uiso calc R 1
H H7B -0.0313 0.4333 0.0573 0.056 Uiso calc R 1
C C8 0.0944(3) 0.5741(3) 0.2071(2) 0.0402(6) Uani d . 1
C C9 0.0614(4) 0.6965(4) 0.1943(2) 0.0565(8) Uani d . 1
H H9 -0.0168 0.6858 0.1335 0.068 Uiso calc R 1
C C10 0.1473(5) 0.8340(4) 0.2738(3) 0.0672(9) Uani d . 1
H H10 0.1255 0.9168 0.2678 0.081 Uiso calc R 1
C C11 0.2642(4) 0.8484(3) 0.3614(3) 0.0582(8) Uani d . 1
H H11 0.3253 0.9412 0.4150 0.070 Uiso calc R 1
C C12 0.2892(4) 0.7227(3) 0.3683(2) 0.0544(7) Uani d . 1
H H12 0.3676 0.7319 0.4285 0.065 Uiso calc R 1
C C13 0.5550(3) 0.4906(3) 0.32137(18) 0.0392(6) Uani d . 1
H H13 0.4965 0.5548 0.3150 0.047 Uiso calc R 1
C C14 0.7029(3) 0.5103(3) 0.2920(2) 0.0497(7) Uani d . 1
H H14 0.7639 0.5899 0.2615 0.060 Uiso calc R 1
C C15 0.7462(4) 0.3939(4) 0.3138(2) 0.0544(8) Uani d . 1
H H15 0.8420 0.3786 0.3004 0.065 Uiso calc R 1
C C16 0.6257(4) 0.3022(3) 0.35723(19) 0.0467(6) Uani d . 1
H H16 0.6238 0.2128 0.3792 0.056 Uiso calc R 1
C C17 0.5068(3) 0.3626(3) 0.36235(17) 0.0363(5) Uani d . 1
C C18 0.3619(3) 0.2982(3) 0.40347(17) 0.0341(5) Uani d . 1
C C19 0.1032(3) 0.2981(3) 0.42747(19) 0.0412(6) Uani d . 1
H H19A 0.0614 0.3743 0.4351 0.049 Uiso calc R 1
H H19B 0.1392 0.2864 0.4957 0.049 Uiso calc R 1
C C20 -0.0426(3) 0.1449(3) 0.35616(19) 0.0368(5) Uani d . 1
C C21 -0.1457(4) 0.0388(3) 0.3968(2) 0.0494(7) Uani d . 1
H H21 -0.1226 0.0591 0.4685 0.059 Uiso calc R 1
C C22 -0.2819(4) -0.0963(3) 0.3312(3) 0.0642(9) Uani d . 1
H H22 -0.3531 -0.1678 0.3577 0.077 Uiso calc R 1
C C23 -0.3121(4) -0.1249(3) 0.2257(3) 0.0643(9) Uani d . 1
H H23 -0.4035 -0.2157 0.1791 0.077 Uiso calc R 1
C C24 -0.2030(4) -0.0151(3) 0.1912(2) 0.0561(8) Uani d . 1
H H24 -0.2227 -0.0347 0.1198 0.067 Uiso calc R 1
Fe Fe1 0.50233(5) 0.29617(4) 0.21164(3) 0.03613(12) Uani d . 1
N N1 0.0872(3) 0.3262(2) 0.12258(16) 0.0412(5) Uani d . 1
H H1N 0.0555 0.2472 0.1458 0.049 Uiso calc R 1
N N2 0.2067(3) 0.5870(2) 0.29298(17) 0.0448(5) Uani d . 1
N N3 0.2504(3) 0.3557(2) 0.39139(15) 0.0367(5) Uani d . 1
H H3N 0.2665 0.4278 0.3618 0.044 Uiso calc R 1
N N4 -0.0694(3) 0.1189(2) 0.25385(16) 0.0449(5) Uani d . 1
O O1 0.2657(3) 0.4695(2) 0.04623(16) 0.0601(6) Uani d . 1
O O2 0.3471(3) 0.1989(2) 0.44891(14) 0.0481(5) Uani d . 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C5 107.5(2) ?
C2 C1 Fe1 70.01(15) ?
C5 C1 Fe1 69.15(14) ?
C2 C1 H1 126.2 ?
C5 C1 H1 126.2 ?
Fe1 C1 H1 126.2 ?
C1 C2 C3 108.7(2) ?
C1 C2 Fe1 69.53(14) ?
C3 C2 Fe1 69.94(15) ?
C1 C2 H2 125.6 ?
C3 C2 H2 125.6 ?
Fe1 C2 H2 125.6 ?
C4 C3 C2 108.0(3) ?
C4 C3 Fe1 69.44(14) ?
C2 C3 Fe1 69.56(15) ?
C4 C3 H3 126.0 ?
C2 C3 H3 126.0 ?
Fe1 C3 H3 126.0 ?
C3 C4 C5 108.2(2) ?
C3 C4 Fe1 70.23(15) ?
C5 C4 Fe1 69.17(14) ?
C3 C4 H4 125.9 ?
C5 C4 H4 125.9 ?
Fe1 C4 H4 125.9 ?
C4 C5 C1 107.5(2) ?
C4 C5 C6 128.1(2) ?
C1 C5 C6 124.4(2) ?
C4 C5 Fe1 69.75(14) ?
C1 C5 Fe1 69.65(14) ?
C6 C5 Fe1 124.96(16) ?
O1 C6 N1 121.7(2) ?
O1 C6 C5 121.9(2) ?
N1 C6 C5 116.4(2) ?
N1 C7 C8 114.6(2) y
N1 C7 H7A 108.6 ?
C8 C7 H7A 108.6 ?
N1 C7 H7B 108.6 ?
C8 C7 H7B 108.6 ?
H7A C7 H7B 107.6 ?
N2 C8 C9 121.8(3) ?
N2 C8 C7 117.3(2) ?
C9 C8 C7 120.8(3) ?
C10 C9 C8 118.5(3) ?
C10 C9 H9 120.8 ?
C8 C9 H9 120.8 ?
C11 C10 C9 119.9(3) ?
C11 C10 H10 120.1 ?
C9 C10 H10 120.1 ?
C10 C11 C12 118.2(3) ?
C10 C11 H11 120.9 ?
C12 C11 H11 120.9 ?
N2 C12 C11 123.4(3) ?
N2 C12 H12 118.3 ?
C11 C12 H12 118.3 ?
C14 C13 C17 108.3(2) ?
C14 C13 Fe1 70.13(15) ?
C17 C13 Fe1 70.12(13) ?
C14 C13 H13 125.8 ?
C17 C13 H13 125.8 ?
Fe1 C13 H13 125.8 ?
C15 C14 C13 108.0(3) ?
C15 C14 Fe1 70.00(16) ?
C13 C14 Fe1 69.16(14) ?
C15 C14 H14 126.0 ?
C13 C14 H14 126.0 ?
Fe1 C14 H14 126.0 ?
C14 C15 C16 108.2(2) ?
C14 C15 Fe1 69.50(15) ?
C16 C15 Fe1 69.79(16) ?
C14 C15 H15 125.9 ?
C16 C15 H15 125.9 ?
Fe1 C15 H15 125.9 ?
C15 C16 C17 107.9(2) ?
C15 C16 Fe1 69.69(16) ?
C17 C16 Fe1 69.35(14) ?
C15 C16 H16 126.1 ?
C17 C16 H16 126.1 ?
Fe1 C16 H16 126.1 ?
C13 C17 C16 107.6(2) ?
C13 C17 C18 128.3(2) ?
C16 C17 C18 124.1(2) ?
C13 C17 Fe1 69.04(13) ?
C16 C17 Fe1 69.84(14) ?
C18 C17 Fe1 126.33(16) ?
O2 C18 N3 121.7(2) ?
O2 C18 C17 121.5(2) ?
N3 C18 C17 116.7(2) ?
N3 C19 C20 114.03(19) y
N3 C19 H19A 108.7 ?
C20 C19 H19A 108.7 ?
N3 C19 H19B 108.7 ?
C20 C19 H19B 108.7 ?
H19A C19 H19B 107.6 ?
N4 C20 C21 122.0(2) ?
N4 C20 C19 117.6(2) ?
C21 C20 C19 120.4(2) ?
C22 C21 C20 119.8(3) ?
C22 C21 H21 120.1 ?
C20 C21 H21 120.1 ?
C21 C22 C23 119.1(3) ?
C21 C22 H22 120.4 ?
C23 C22 H22 120.4 ?
C24 C23 C22 117.8(3) ?
C24 C23 H23 121.1 ?
C22 C23 H23 121.1 ?
N4 C24 C23 124.3(3) ?
N4 C24 H24 117.8 ?
C23 C24 H24 117.8 ?
C13 Fe1 C5 106.64(10) ?
C13 Fe1 C1 120.44(11) ?
C5 Fe1 C1 41.20(10) ?
C13 Fe1 C4 124.54(10) ?
C5 Fe1 C4 41.08(10) ?
C1 Fe1 C4 68.91(10) ?
C13 Fe1 C14 40.71(10) ?
C5 Fe1 C14 122.50(11) ?
C1 Fe1 C14 105.58(11) ?
C4 Fe1 C14 160.32(12) ?
C13 Fe1 C17 40.84(10) ?
C5 Fe1 C17 122.05(10) ?
C1 Fe1 C17 157.18(10) ?
C4 Fe1 C17 108.83(10) ?
C14 Fe1 C17 68.53(10) ?
C13 Fe1 C2 156.06(11) ?
C5 Fe1 C2 68.49(11) ?
C1 Fe1 C2 40.46(11) ?
C4 Fe1 C2 68.11(11) ?
C14 Fe1 C2 120.70(11) ?
C17 Fe1 C2 161.53(11) ?
C13 Fe1 C15 68.38(11) ?
C5 Fe1 C15 158.94(12) ?
C1 Fe1 C15 122.25(11) ?
C4 Fe1 C15 158.36(12) ?
C14 Fe1 C15 40.50(12) ?
C17 Fe1 C15 68.43(10) ?
C2 Fe1 C15 107.29(11) ?
C13 Fe1 C16 68.56(11) ?
C5 Fe1 C16 158.65(11) ?
C1 Fe1 C16 159.42(11) ?
C4 Fe1 C16 123.33(11) ?
C14 Fe1 C16 68.29(12) ?
C17 Fe1 C16 40.81(10) ?
C2 Fe1 C16 124.40(11) ?
C15 Fe1 C16 40.52(11) ?
C13 Fe1 C3 161.57(11) ?
C5 Fe1 C3 68.56(11) ?
C1 Fe1 C3 68.47(11) ?
C4 Fe1 C3 40.33(11) ?
C14 Fe1 C3 156.96(11) ?
C17 Fe1 C3 125.43(11) ?
C2 Fe1 C3 40.51(11) ?
C15 Fe1 C3 122.51(12) ?
C16 Fe1 C3 109.05(12) ?
C6 N1 C7 121.4(2) ?
C6 N1 H1N 119.3 ?
C7 N1 H1N 119.3 ?
C8 N2 C12 118.2(2) ?
C18 N3 C19 120.6(2) ?
C18 N3 H3N 119.7 ?
C19 N3 H3N 119.7 ?
C20 N4 C24 117.0(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.414(4) ?
C1 C5 1.434(3) ?
C1 Fe1 2.042(2) ?
C1 H1 0.9800 ?
C2 C3 1.420(4) ?
C2 Fe1 2.048(2) ?
C2 H2 0.9800 ?
C3 C4 1.412(4) ?
C3 Fe1 2.053(3) ?
C3 H3 0.9800 ?
C4 C5 1.431(3) ?
C4 Fe1 2.043(3) ?
C4 H4 0.9800 ?
C5 C6 1.480(4) y
C5 Fe1 2.035(2) ?
C6 O1 1.231(3) y
C6 N1 1.346(3) y
C7 N1 1.444(3) y
C7 C8 1.514(4) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 N2 1.331(3) ?
C8 C9 1.390(4) ?
C9 C10 1.379(4) ?
C9 H9 0.9300 ?
C10 C11 1.363(5) ?
C10 H10 0.9300 ?
C11 C12 1.367(4) ?
C11 H11 0.9300 ?
C12 N2 1.340(3) ?
C12 H12 0.9300 ?
C13 C14 1.417(4) ?
C13 C17 1.422(3) ?
C13 Fe1 2.031(2) ?
C13 H13 0.9800 ?
C14 C15 1.417(4) ?
C14 Fe1 2.044(3) ?
C14 H14 0.9800 ?
C15 C16 1.420(4) ?
C15 Fe1 2.050(3) ?
C15 H15 0.9800 ?
C16 C17 1.428(3) ?
C16 Fe1 2.052(3) ?
C16 H16 0.9800 ?
C17 C18 1.477(3) y
C17 Fe1 2.045(2) ?
C18 O2 1.233(3) y
C18 N3 1.337(3) y
C19 N3 1.442(3) y
C19 C20 1.512(3) ?
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C20 N4 1.334(3) ?
C20 C21 1.381(3) ?
C21 C22 1.368(4) ?
C21 H21 0.9300 ?
C22 C23 1.372(4) ?
C22 H22 0.9300 ?
C23 C24 1.370(4) ?
C23 H23 0.9300 ?
C24 N4 1.342(3) ?
C24 H24 0.9300 ?
N1 H1N 0.8600 ?
N3 H3N 0.8600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N N4 . 0.86 2.30 3.079(3) 151 yes
N3 H3N N2 . 0.86 2.16 2.974(3) 157 yes
C1 H1 O1 2_665 0.98 2.52 3.452(4) 159 yes
C11 H11 O2 1_565 0.93 2.43 3.173(4) 137 yes
C12 H12 O2 2_666 0.93 2.49 3.374(4) 158 yes
