#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/15/4081556.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_4081556
loop_
_publ_author_name
'Tampier, Stefan'
'Bleifuss, Sascha M.'
'Abd-Elzaher, Mokhles M.'
'Sutter, Jörg'
'Heinemann, Frank W.'
'Burzlaff, Nicolai'
_publ_section_title
;
 Bis(pyrazol-1-yl)acetic Acid Bearing Ferrocenyl Substituents
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              5935
_journal_paper_doi               10.1021/om400495f
_journal_volume                  32
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C31 H30 Fe2 N4 O1'
_chemical_formula_sum            'C31 H30 Fe2 N4 O'
_chemical_formula_weight         586.29
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-01-21T20:34:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 116.878(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.538(3)
_cell_length_b                   7.5557(10)
_cell_length_c                   13.5237(15)
_cell_measurement_reflns_used    201
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      6
_cell_measurement_wavelength     0.71073
_cell_volume                     2509.9(5)
_computing_cell_refinement       'EVALCCD (Duisenberg, 2003)'
_computing_data_collection       'COLLECT (Bruker-Nonius, 2002)'
_computing_data_reduction        'EVALCCD (Duisenberg, 2003)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method
;
 φ- and ω-rotations with 2.00 ° and 76 sec per frame
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36492
_diffrn_reflns_theta_full        29.01
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    1.19
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.87009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.08
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0345P)²+2.8640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                2855
_reflns_number_total             3332
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400495f_si_001.cif
_cod_data_source_block           compound6
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C31 H30 Fe2 N4 O1'
_cod_database_code               4081556
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'
'-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
C1 C 0 0.7200(3) 0.25 0.0184(4) Uani 1 2 d S
C11 C 0.04073(7) 0.2294(2) 0.07348(14) 0.0196(3) Uani 1 1 d .
H11A H 0.0164 0.158 0.0897 0.029 Uiso 1 1 calc R
H11B H 0.0753 0.1711 0.1002 0.029 Uiso 1 1 calc R
H11C H 0.0258 0.2461 -0.0052 0.029 Uiso 1 1 calc R
C12 C 0.04805(6) 0.4055(2) 0.12918(12) 0.0146(3) Uani 1 1 d .
C13 C 0.09216(6) 0.52889(19) 0.15992(12) 0.0136(3) Uani 1 1 d .
C14 C 0.08022(6) 0.6651(2) 0.21307(12) 0.0143(3) Uani 1 1 d .
C15 C 0.11090(7) 0.8297(2) 0.26601(14) 0.0212(3) Uani 1 1 d .
H15A H 0.1294 0.8143 0.345 0.032 Uiso 1 1 calc R
H15B H 0.086 0.9272 0.248 0.032 Uiso 1 1 calc R
H15C H 0.1371 0.8534 0.2391 0.032 Uiso 1 1 calc R
C21 C 0.14005(6) 0.5073(2) 0.13977(12) 0.0158(3) Uani 1 1 d .
C22 C 0.19443(7) 0.5721(2) 0.20592(13) 0.0209(3) Uani 1 1 d .
H22 H 0.2059 0.639 0.2703 0.025 Uiso 1 1 calc R
C23 C 0.22772(7) 0.5160(2) 0.15579(15) 0.0249(4) Uani 1 1 d .
H23 H 0.2646 0.5405 0.1818 0.03 Uiso 1 1 calc R
C24 C 0.19494(7) 0.4165(2) 0.05944(16) 0.0248(4) Uani 1 1 d .
H24 H 0.2066 0.364 0.0117 0.03 Uiso 1 1 calc R
C25 C 0.14081(7) 0.4111(2) 0.04872(14) 0.0195(3) Uani 1 1 d .
H25 H 0.1112 0.3548 -0.0076 0.023 Uiso 1 1 calc R
C31 C 0.10985(6) 0.8718(2) -0.00910(13) 0.0179(3) Uani 1 1 d .
H31 H 0.0814 0.8914 0.0088 0.022 Uiso 1 1 calc R
C32 C 0.16371(7) 0.9391(2) 0.04987(13) 0.0195(3) Uani 1 1 d .
H32 H 0.1766 1.0103 0.1127 0.023 Uiso 1 1 calc R
C33 C 0.19445(7) 0.8781(2) -0.00417(14) 0.0198(3) Uani 1 1 d .
H33 H 0.231 0.9022 0.0172 0.024 Uiso 1 1 calc R
C34 C 0.15933(7) 0.7731(2) -0.09725(13) 0.0196(3) Uani 1 1 d .
H34 H 0.169 0.7171 -0.1471 0.024 Uiso 1 1 calc R
C35 C 0.10690(7) 0.7695(2) -0.10017(13) 0.0188(3) Uani 1 1 d .
H35 H 0.0763 0.7108 -0.1522 0.023 Uiso 1 1 calc R
Fe Fe 0.164348(8) 0.66689(3) 0.046836(17) 0.01261(7) Uani 1 1 d .
N11 N 0.03149(5) 0.61843(17) 0.21321(10) 0.0149(3) Uani 1 1 d .
N12 N 0.01159(5) 0.45865(17) 0.16083(10) 0.0156(3) Uani 1 1 d .
O1 O 0 0.8791(2) 0.25 0.0336(5) Uani 1 2 d S
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 0 '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 0.006 '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
O1 C1 N11 123.07(10) . 2
O1 C1 N11 123.07(10) . .
N11 C1 N11 113.86(19) 2 .
C12 C11 H11A 109.5 . .
C12 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C12 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N12 C12 C13 112.15(13) . .
N12 C12 C11 118.97(14) . .
C13 C12 C11 128.81(14) . .
C14 C13 C12 105.42(13) . .
C14 C13 C21 128.66(14) . .
C12 C13 C21 125.91(14) . .
C13 C14 N11 105.66(13) . .
C13 C14 C15 131.00(14) . .
N11 C14 C15 123.31(13) . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C25 C21 C22 106.87(13) . .
C25 C21 C13 125.15(14) . .
C22 C21 C13 127.97(14) . .
C25 C21 Fe 68.84(8) . .
C22 C21 Fe 69.30(9) . .
C13 C21 Fe 127.88(11) . .
C23 C22 C21 108.35(15) . .
C23 C22 Fe 69.38(9) . .
C21 C22 Fe 69.74(9) . .
C23 C22 H22 125.8 . .
C21 C22 H22 125.8 . .
Fe C22 H22 126.6 . .
C24 C23 C22 108.34(15) . .
C24 C23 Fe 69.70(10) . .
C22 C23 Fe 69.84(9) . .
C24 C23 H23 125.8 . .
C22 C23 H23 125.8 . .
Fe C23 H23 126.2 . .
C23 C24 C25 108.00(15) . .
C23 C24 Fe 69.73(10) . .
C25 C24 Fe 69.35(9) . .
C23 C24 H24 126 . .
C25 C24 H24 126 . .
Fe C24 H24 126.5 . .
C24 C25 C21 108.45(15) . .
C24 C25 Fe 69.67(9) . .
C21 C25 Fe 70.10(9) . .
C24 C25 H25 125.8 . .
C21 C25 H25 125.8 . .
Fe C25 H25 126 . .
C32 C31 C35 108.41(14) . .
C32 C31 Fe 70.05(9) . .
C35 C31 Fe 69.81(9) . .
C32 C31 H31 125.8 . .
C35 C31 H31 125.8 . .
Fe C31 H31 125.9 . .
C33 C32 C31 107.95(14) . .
C33 C32 Fe 69.72(9) . .
C31 C32 Fe 69.39(9) . .
C33 C32 H32 126 . .
C31 C32 H32 126 . .
Fe C32 H32 126.4 . .
C32 C33 C34 108.00(14) . .
C32 C33 Fe 69.82(9) . .
C34 C33 Fe 69.53(9) . .
C32 C33 H33 126 . .
C34 C33 H33 126 . .
Fe C33 H33 126.2 . .
C35 C34 C33 107.95(14) . .
C35 C34 Fe 69.63(9) . .
C33 C34 Fe 69.71(9) . .
C35 C34 H34 126 . .
C33 C34 H34 126 . .
Fe C34 H34 126.2 . .
C31 C35 C34 107.70(14) . .
C31 C35 Fe 69.51(9) . .
C34 C35 Fe 69.71(9) . .
C31 C35 H35 126.2 . .
C34 C35 H35 126.2 . .
Fe C35 H35 126.2 . .
C25 Fe C24 40.98(7) . .
C25 Fe C23 68.65(7) . .
C24 Fe C23 40.57(8) . .
C25 Fe C31 122.44(7) . .
C24 Fe C31 159.21(7) . .
C23 Fe C31 158.53(7) . .
C25 Fe C35 105.04(7) . .
C24 Fe C35 122.53(7) . .
C23 Fe C35 160.12(7) . .
C31 Fe C35 40.68(6) . .
C25 Fe C22 68.70(7) . .
C24 Fe C22 68.55(7) . .
C23 Fe C22 40.78(7) . .
C31 Fe C22 122.13(7) . .
C35 Fe C22 156.33(7) . .
C25 Fe C34 119.74(7) . .
C24 Fe C34 106.80(7) . .
C23 Fe C34 124.78(7) . .
C31 Fe C34 68.30(6) . .
C35 Fe C34 40.66(6) . .
C22 Fe C34 162.32(7) . .
C25 Fe C33 156.50(7) . .
C24 Fe C33 122.16(7) . .
C23 Fe C33 109.39(7) . .
C31 Fe C33 68.19(6) . .
C35 Fe C33 68.47(7) . .
C22 Fe C33 126.12(7) . .
C34 Fe C33 40.76(7) . .
C25 Fe C32 160.09(7) . .
C24 Fe C32 158.34(7) . .
C23 Fe C32 123.68(7) . .
C31 Fe C32 40.55(6) . .
C35 Fe C32 68.41(7) . .
C22 Fe C32 109.32(7) . .
C34 Fe C32 68.32(7) . .
C33 Fe C32 40.45(6) . .
C25 Fe C21 41.06(6) . .
C24 Fe C21 69.09(6) . .
C23 Fe C21 68.97(6) . .
C31 Fe C21 106.38(6) . .
C35 Fe C21 119.43(6) . .
C22 Fe C21 40.97(6) . .
C34 Fe C21 155.07(7) . .
C33 Fe C21 161.94(7) . .
C32 Fe C21 124.40(6) . .
N12 N11 C14 112.39(12) . .
N12 N11 C1 119.55(13) . .
C14 N11 C1 127.79(13) . .
C12 N12 N11 104.38(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.202(3) .
C1 N11 1.4068(18) 2
C1 N11 1.4068(18) .
C11 C12 1.498(2) .
C11 H11A 0.96 .
C11 H11B 0.96 .
C11 H11C 0.96 .
C12 N12 1.3194(19) .
C12 C13 1.435(2) .
C13 C14 1.378(2) .
C13 C21 1.471(2) .
C14 N11 1.3882(19) .
C14 C15 1.492(2) .
C15 H15A 0.96 .
C15 H15B 0.96 .
C15 H15C 0.96 .
C21 C25 1.438(2) .
C21 C22 1.439(2) .
C21 Fe 2.0594(15) .
C22 C23 1.429(2) .
C22 Fe 2.0534(16) .
C22 H22 0.93 .
C23 C24 1.419(3) .
C23 Fe 2.0472(16) .
C23 H23 0.93 .
C24 C25 1.431(2) .
C24 Fe 2.0468(17) .
C24 H24 0.93 .
C25 Fe 2.0425(16) .
C25 H25 0.93 .
C31 C32 1.423(2) .
C31 C35 1.425(2) .
C31 Fe 2.0484(16) .
C31 H31 0.93 .
C32 C33 1.422(2) .
C32 Fe 2.0571(17) .
C32 H32 0.93 .
C33 C34 1.431(2) .
C33 Fe 2.0559(16) .
C33 H33 0.93 .
C34 C35 1.427(2) .
C34 Fe 2.0535(15) .
C34 H34 0.93 .
C35 Fe 2.0524(16) .
C35 H35 0.93 .
N11 N12 1.3815(18) .
