#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:48:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180356 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/25/7202517.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_7202517
loop_
_publ_author_name
'Braga, Dario'
'Giaffreda, Stefano Luca'
'Rubini, Katia'
'Grepioni, Fabrizia'
'Chierotti, Michele R.'
'Gobetto, Roberto'
_publ_section_title
;
 Making crystals from crystals: three solvent-free routes to the
 hydrogen bonded co-crystal between 1,1?-di-pyridyl-ferrocene and
 anthranilic acid
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              39
_journal_paper_doi               10.1039/b613569b
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C27 H23 Fe N3 O2'
_chemical_formula_weight         477.33
_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                99.77(3)
_cell_angle_beta                 94.17(4)
_cell_angle_gamma                115.74(7)
_cell_formula_units_Z            2
_cell_length_a                   9.565(9)
_cell_length_b                   9.897(4)
_cell_length_c                   13.201(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1094.2(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0384
_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       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4010
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.866
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.570
_refine_diff_density_min         -1.426
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0843
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2221
_refine_ls_wR_factor_ref         0.2491
_reflns_number_gt                2740
_reflns_number_total             3829
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b613569b.txt
_cod_data_source_block           sg0107
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Psi-scan' changed to
'psi-scan' 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_original_cell_volume        1094.2(12)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7202517
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.34775(8) -0.11960(8) 0.16931(5) 0.0398(3) Uani 1 1 d . . .
C1 C 0.5302(4) 0.0241(4) 0.2884(3) 0.0502(13) Uani 1 1 d G . .
H1 H 0.6256 0.0214 0.3023 0.060 Uiso 1 1 calc R . .
C2 C 0.4979(5) 0.1107(4) 0.2230(3) 0.0664(19) Uani 1 1 d G . .
H2 H 0.5683 0.1746 0.1866 0.080 Uiso 1 1 calc R . .
C3 C 0.3391(6) 0.0825(5) 0.2230(3) 0.072(2) Uani 1 1 d G . .
H3 H 0.2873 0.1248 0.1866 0.086 Uiso 1 1 calc R . .
C4 C 0.2733(4) -0.0215(5) 0.2884(3) 0.0618(17) Uani 1 1 d G . .
H4 H 0.1709 -0.0593 0.3023 0.074 Uiso 1 1 calc R . .
C5 C 0.3915(4) -0.0576(4) 0.3288(3) 0.0434(12) Uani 1 1 d G . .
C6 C 0.3728(6) -0.1638(6) 0.3984(4) 0.0424(12) Uani 1 1 d . . .
C7 C 0.2342(7) -0.2367(8) 0.4376(4) 0.0588(16) Uani 1 1 d . . .
H7 H 0.1479 -0.2203 0.4197 0.071 Uiso 1 1 calc R . .
C8 C 0.2263(10) -0.3338(9) 0.5035(5) 0.076(2) Uani 1 1 d . . .
H8 H 0.1330 -0.3818 0.5289 0.091 Uiso 1 1 calc R . .
C9 C 0.4778(9) -0.2931(7) 0.4954(5) 0.0629(17) Uani 1 1 d . . .
H9 H 0.5620 -0.3118 0.5151 0.075 Uiso 1 1 calc R . .
C10 C 0.4956(7) -0.1954(6) 0.4295(4) 0.0491(13) Uani 1 1 d . . .
H10 H 0.5905 -0.1499 0.4053 0.059 Uiso 1 1 calc R . .
C11 C 0.3973(4) -0.2909(5) 0.1013(3) 0.0488(13) Uani 1 1 d G . .
H11 H 0.4773 -0.3114 0.1274 0.059 Uiso 1 1 calc R . .
C12 C 0.4104(4) -0.1903(4) 0.0336(3) 0.0561(14) Uani 1 1 d G . .
H12 H 0.5005 -0.1334 0.0075 0.067 Uiso 1 1 calc R . .
C13 C 0.2619(5) -0.1919(4) 0.0126(3) 0.0580(15) Uani 1 1 d G . .
H13 H 0.2376 -0.1363 -0.0296 0.070 Uiso 1 1 calc R . .
C14 C 0.1570(3) -0.2935(4) 0.0674(3) 0.0509(13) Uani 1 1 d G . .
H14 H 0.0520 -0.3160 0.0674 0.061 Uiso 1 1 calc R . .
C15 C 0.2407(4) -0.3547(4) 0.1222(3) 0.0409(11) Uani 1 1 d G . .
C16 C 0.1772(6) -0.4658(5) 0.1882(4) 0.0398(11) Uani 1 1 d . . .
C17 C 0.0209(7) -0.5241(7) 0.2030(4) 0.0506(13) Uani 1 1 d . . .
H17 H -0.0451 -0.4910 0.1717 0.061 Uiso 1 1 calc R . .
C18 C -0.0362(8) -0.6291(7) 0.2631(5) 0.0631(17) Uani 1 1 d . . .
H18 H -0.1415 -0.6653 0.2705 0.076 Uiso 1 1 calc R . .
C19 C 0.1993(9) -0.6268(7) 0.2984(5) 0.0629(17) Uani 1 1 d . . .
H19 H 0.2625 -0.6614 0.3314 0.075 Uiso 1 1 calc R . .
C20 C 0.2679(7) -0.5207(7) 0.2388(4) 0.0517(14) Uani 1 1 d . . .
H20 H 0.3735 -0.4862 0.2326 0.062 Uiso 1 1 calc R . .
N1 N 0.3449(9) -0.3619(6) 0.5322(4) 0.0706(16) Uani 1 1 d . . .
N2 N 0.0481(8) -0.6839(6) 0.3122(4) 0.0675(15) Uani 1 1 d . . .
C21 C 0.2706(7) 0.3747(7) 0.8542(5) 0.0505(13) Uani 1 1 d . . .
H21 H 0.3197 0.4807 0.8605 0.061 Uiso 1 1 calc R . .
C22 C 0.2522(8) 0.3179(8) 0.9430(5) 0.0581(15) Uani 1 1 d . . .
H22 H 0.2871 0.3843 1.0084 0.070 Uiso 1 1 calc R . .
C23 C 0.1811(8) 0.1608(8) 0.9334(5) 0.0593(15) Uani 1 1 d . . .
H23 H 0.1678 0.1214 0.9931 0.071 Uiso 1 1 calc R . .
C24 C 0.1295(7) 0.0617(8) 0.8374(5) 0.0553(14) Uani 1 1 d . . .
H24 H 0.0834 -0.0438 0.8334 0.066 Uiso 1 1 calc R . .
C25 C 0.1446(6) 0.1149(7) 0.7455(5) 0.0488(13) Uani 1 1 d . . .
N3 N 0.0936(8) 0.0132(8) 0.6513(5) 0.0614(14) Uani 1 1 d . . .
H300 H 0.071(9) -0.073(10) 0.648(6) 0.07(3) Uiso 1 1 d . . .
H301 H 0.081(12) 0.042(11) 0.608(8) 0.09(3) Uiso 1 1 d . . .
C26 C 0.2177(6) 0.2777(6) 0.7545(4) 0.0433(12) Uani 1 1 d . . .
C27 C 0.2343(7) 0.3443(7) 0.6613(5) 0.0547(14) Uani 1 1 d . . .
O1 O 0.1719(6) 0.2692(6) 0.5734(3) 0.0719(13) Uani 1 1 d . . .
O2 O 0.3238(6) 0.4936(5) 0.6827(4) 0.0762(14) Uani 1 1 d . . .
H200 H 0.3294 0.5247 0.6287 0.114 Uiso 1 1 calc R . .
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'
Fe Fe 0.3463 0.8444 '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'
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
C11 Fe C12 40.78(7) . . ?
C11 Fe C4 150.55(16) . . ?
C12 Fe C4 168.13(16) . . ?
C11 Fe C3 167.17(18) . . ?
C12 Fe C3 128.87(17) . . ?
C4 Fe C3 40.67(8) . . ?
C11 Fe C5 117.06(14) . . ?
C12 Fe C5 149.17(16) . . ?
C4 Fe C5 40.65(7) . . ?
C3 Fe C5 68.30(9) . . ?
C11 Fe C15 40.68(8) . . ?
C12 Fe C15 68.42(9) . . ?
C4 Fe C15 118.40(16) . . ?
C3 Fe C15 151.02(18) . . ?
C5 Fe C15 109.48(13) . . ?
C11 Fe C13 68.40(9) . . ?
C12 Fe C13 40.64(8) . . ?
C4 Fe C13 130.50(16) . . ?
C3 Fe C13 108.42(14) . . ?
C5 Fe C13 169.46(16) . . ?
C15 Fe C13 68.18(9) . . ?
C11 Fe C2 128.62(18) . . ?
C12 Fe C2 107.07(15) . . ?
C4 Fe C2 68.25(10) . . ?
C3 Fe C2 40.53(8) . . ?
C5 Fe C2 68.13(9) . . ?
C15 Fe C2 167.71(17) . . ?
C13 Fe C2 116.42(15) . . ?
C11 Fe C1 107.71(15) . . ?
C12 Fe C1 115.85(15) . . ?
C4 Fe C1 68.23(10) . . ?
C3 Fe C1 68.15(11) . . ?
C5 Fe C1 40.49(7) . . ?
C15 Fe C1 130.07(15) . . ?
C13 Fe C1 148.81(16) . . ?
C2 Fe C1 40.43(8) . . ?
C11 Fe C14 68.28(10) . . ?
C12 Fe C14 68.25(10) . . ?
C4 Fe C14 109.93(16) . . ?
C3 Fe C14 117.98(16) . . ?
C5 Fe C14 131.26(15) . . ?
C15 Fe C14 40.47(8) . . ?
C13 Fe C14 40.45(7) . . ?
C2 Fe C14 149.90(16) . . ?
C1 Fe C14 169.12(15) . . ?
C2 C1 C5 108.0 . . ?
C2 C1 Fe 69.73(15) . . ?
C5 C1 Fe 69.44(16) . . ?
C2 C1 H1 126.0 . . ?
C5 C1 H1 126.0 . . ?
Fe C1 H1 126.4 . . ?
C3 C2 C1 108.0 . . ?
C3 C2 Fe 69.39(17) . . ?
C1 C2 Fe 69.84(15) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe C2 H2 126.3 . . ?
C2 C3 C4 108.0 . . ?
C2 C3 Fe 70.08(17) . . ?
C4 C3 Fe 69.51(15) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
Fe C3 H3 126.0 . . ?
C5 C4 C3 108.0 . . ?
C5 C4 Fe 69.92(15) . . ?
C3 C4 Fe 69.82(15) . . ?
C5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
Fe C4 H4 125.8 . . ?
C4 C5 C1 108.0 . . ?
C4 C5 C6 126.2(3) . . ?
C1 C5 C6 125.8(3) . . ?
C4 C5 Fe 69.43(15) . . ?
C1 C5 Fe 70.06(16) . . ?
C6 C5 Fe 125.0(3) . . ?
C7 C6 C10 116.3(5) . . ?
C7 C6 C5 122.7(5) . . ?
C10 C6 C5 121.0(5) . . ?
C8 C7 C6 119.3(6) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
N1 C8 C7 123.4(7) . . ?
N1 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
N1 C9 C10 122.5(7) . . ?
N1 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C6 120.7(6) . . ?
C9 C10 H10 119.7 . . ?
C6 C10 H10 119.7 . . ?
C15 C11 C12 108.0 . . ?
C15 C11 Fe 70.09(15) . . ?
C12 C11 Fe 69.67(15) . . ?
C15 C11 H11 126.0 . . ?
C12 C11 H11 126.0 . . ?
Fe C11 H11 125.8 . . ?
C13 C12 C11 108.0 . . ?
C13 C12 Fe 70.15(15) . . ?
C11 C12 Fe 69.55(14) . . ?
C13 C12 H12 126.0 . . ?
C11 C12 H12 126.0 . . ?
Fe C12 H12 125.9 . . ?
C14 C13 C12 108.0 . . ?
C14 C13 Fe 70.01(15) . . ?
C12 C13 Fe 69.22(15) . . ?
C14 C13 H13 126.0 . . ?
C12 C13 H13 126.0 . . ?
Fe C13 H13 126.3 . . ?
C13 C14 C15 108.0 . . ?
C13 C14 Fe 69.55(15) . . ?
C15 C14 Fe 69.44(15) . . ?
C13 C14 H14 126.0 . . ?
C15 C14 H14 126.0 . . ?
Fe C14 H14 126.6 . . ?
C11 C15 C14 108.0 . . ?
C11 C15 C16 125.6(3) . . ?
C14 C15 C16 126.4(3) . . ?
C11 C15 Fe 69.23(16) . . ?
C14 C15 Fe 70.08(15) . . ?
C16 C15 Fe 126.8(3) . . ?
C20 C16 C17 115.8(5) . . ?
C20 C16 C15 122.6(5) . . ?
C17 C16 C15 121.6(5) . . ?
C18 C17 C16 120.6(6) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
N2 C18 C17 124.7(6) . . ?
N2 C18 H18 117.6 . . ?
C17 C18 H18 117.6 . . ?
N2 C19 C20 125.0(6) . . ?
N2 C19 H19 117.5 . . ?
C20 C19 H19 117.5 . . ?
C16 C20 C19 119.2(6) . . ?
C16 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C8 N1 C9 118.0(6) . . ?
C18 N2 C19 114.6(5) . . ?
C22 C21 C26 121.9(6) . . ?
C22 C21 H21 119.0 . . ?
C26 C21 H21 119.0 . . ?
C21 C22 C23 118.9(6) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C24 C23 C22 121.1(6) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 121.7(6) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
N3 C25 C24 120.3(6) . . ?
N3 C25 C26 122.1(6) . . ?
C24 C25 C26 117.7(5) . . ?
C25 N3 H300 120(6) . . ?
C25 N3 H301 116(8) . . ?
H300 N3 H301 124(10) . . ?
C21 C26 C25 118.7(5) . . ?
C21 C26 C27 119.9(5) . . ?
C25 C26 C27 121.4(5) . . ?
O1 C27 O2 122.9(6) . . ?
O1 C27 C26 123.8(6) . . ?
O2 C27 C26 113.3(5) . . ?
C27 O2 H200 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
Fe C11 2.037(4) . ?
Fe C12 2.038(4) . ?
Fe C4 2.041(4) . ?
Fe C3 2.045(4) . ?
Fe C5 2.048(4) . ?
Fe C15 2.048(4) . ?
Fe C13 2.051(4) . ?
Fe C2 2.054(4) . ?
Fe C1 2.056(4) . ?
Fe C14 2.057(4) . ?
C1 C2 1.4200 . ?
C1 C5 1.4200 . ?
C1 H1 0.9300 . ?
C2 C3 1.4200 . ?
C2 H2 0.9300 . ?
C3 C4 1.4200 . ?
C3 H3 0.9300 . ?
C4 C5 1.4200 . ?
C4 H4 0.9300 . ?
C5 C6 1.474(6) . ?
C6 C7 1.393(8) . ?
C6 C10 1.391(8) . ?
C7 C8 1.385(10) . ?
C7 H7 0.9300 . ?
C8 N1 1.325(11) . ?
C8 H8 0.9300 . ?
C9 N1 1.329(9) . ?
C9 C10 1.373(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C15 1.4200 . ?
C11 C12 1.4200 . ?
C11 H11 0.9300 . ?
C12 C13 1.4200 . ?
C12 H12 0.9300 . ?
C13 C14 1.4200 . ?
C13 H13 0.9300 . ?
C14 C15 1.4200 . ?
C14 H14 0.9300 . ?
C15 C16 1.469(6) . ?
C16 C20 1.394(8) . ?
C16 C17 1.392(8) . ?
C17 C18 1.363(9) . ?
C17 H17 0.9300 . ?
C18 N2 1.337(9) . ?
C18 H18 0.9300 . ?
C19 N2 1.344(9) . ?
C19 C20 1.381(9) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.374(9) . ?
C21 C26 1.401(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.395(8) . ?
C24 H24 0.9300 . ?
C25 N3 1.363(8) . ?
C25 C26 1.430(8) . ?
N3 H300 0.78(9) . ?
N3 H301 0.70(10) . ?
C26 C27 1.478(8) . ?
C27 O1 1.216(7) . ?
C27 O2 1.311(8) . ?
O2 H200 0.8200 . ?
