#------------------------------------------------------------------------------
#$Date: 2022-02-22 04:59:25 +0200 (Tue, 22 Feb 2022) $
#$Revision: 273082 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/25/2022575.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_2022575
loop_
_publ_author_name
'Kunchur, Harish S.'
'Mondal, Dipanjan'
'Rao, Sowmya'
'Mague, Joel T.'
'Balakrishna, Maravanji S.'
_publ_section_title
;
 Synthesis, structural, characterization and Hirshfeld analysis of a
 bisselenide and a zinc complex of a new hemilabile
 ferrocenylbisphosphane,
 [Fe{C₅H₄P(C₆H₄CH₂NMe₂-o)₂}₂]
;
_journal_coeditor_code           ZO3012
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              725
_journal_page_last               733
_journal_paper_doi               10.1107/S205322962101072X
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          '[Fe (C23 H28 N2 P1 Se1)2]'
_chemical_formula_moiety         'C46 H56 Fe N4 P2 Se2'
_chemical_formula_sum            'C46 H56 Fe N4 P2 Se2'
_chemical_formula_weight         940.65
_chemical_name_systematic
;
(Ferrocene-1,1'-diyl)bis(bis{2-[(dimethylamino)methyl]phenyl}phosphine
selenide)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                93.969(5)
_cell_angle_beta                 97.973(5)
_cell_angle_gamma                94.312(5)
_cell_formula_units_Z            1
_cell_length_a                   9.244(4)
_cell_length_b                   10.465(5)
_cell_length_c                   10.998(5)
_cell_measurement_reflns_used    9535
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.4275
_cell_measurement_theta_min      2.6004
_cell_volume                     1047.2(8)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX2 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Bruker, 2015) and
CELL_NOW (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17800
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.427
_diffrn_reflns_theta_min         1.876
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.213
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.043
_refine_diff_density_max         1.627
_refine_diff_density_min         -1.836
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1155P)²+0.5035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.1700
_reflns_number_gt                4250
_reflns_number_total             4853
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zo3012sup1.cif
_cod_data_source_block           Compound_2
_cod_original_cell_volume        1047.3(8)
_cod_database_code               2022575
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.630
_shelx_estimated_absorpt_t_max   0.911
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se1 0.58085(4) -0.03032(3) 0.79310(3) 0.01609(15) Uani d 1 . .
Fe Fe1 1.0000 0.0000 1.0000 0.01219(19) Uani d 1 . .
P P1 0.73340(10) 0.13251(8) 0.80505(8) 0.0104(2) Uani d 1 . .
N N1 0.8698(3) 0.5733(3) 0.8098(3) 0.0158(6) Uani d 1 . .
N N2 0.3408(3) 0.2702(3) 0.5700(3) 0.0178(7) Uani d 1 . .
C C1 0.9188(4) 0.0974(3) 0.8535(3) 0.0124(7) Uani d 1 . .
C C2 0.9808(4) -0.0162(4) 0.8118(4) 0.0181(7) Uani d 1 . .
H H2 0.9299 -0.0860 0.7593 0.022 Uiso calc 1 . .
C C3 1.1312(5) -0.0067(4) 0.8622(4) 0.0243(9) Uani d 1 . .
H H3 1.1986 -0.0685 0.8484 0.029 Uiso calc 1 . .
C C4 1.1644(4) 0.1118(4) 0.9374(4) 0.0230(9) Uani d 1 . .
H H4 1.2572 0.1423 0.9824 0.028 Uiso calc 1 . .
C C5 1.0332(4) 0.1761(4) 0.9328(4) 0.0153(7) Uani d 1 . .
H H5 1.0232 0.2567 0.9746 0.018 Uiso calc 1 . .
C C6 0.7016(4) 0.2650(3) 0.9129(3) 0.0119(7) Uani d 1 . .
C C7 0.7644(4) 0.3932(3) 0.9159(3) 0.0123(7) Uani d 1 . .
C C8 0.7250(4) 0.4836(3) 1.0030(4) 0.0158(7) Uani d 1 . .
H H8 0.7640 0.5706 1.0057 0.019 Uiso calc 1 . .
C C9 0.6306(4) 0.4495(4) 1.0851(4) 0.0186(8) Uani d 1 . .
H H9 0.6058 0.5129 1.1430 0.022 Uiso calc 1 . .
C C10 0.5722(4) 0.3229(4) 1.0830(4) 0.0166(7) Uani d 1 . .
H H10 0.5090 0.2990 1.1403 0.020 Uiso calc 1 . .
C C11 0.6071(4) 0.2317(3) 0.9964(3) 0.0136(7) Uani d 1 . .
H H11 0.5660 0.1455 0.9940 0.016 Uiso calc 1 . .
C C12 0.8757(4) 0.4383(3) 0.8365(3) 0.0138(7) Uani d 1 . .
H H12A 0.9750 0.4263 0.8785 0.017 Uiso calc 1 . .
H H12B 0.8594 0.3839 0.7578 0.017 Uiso calc 1 . .
C C13 0.7362(4) 0.5912(4) 0.7259(4) 0.0241(9) Uani d 1 . .
H H13A 0.7321 0.6826 0.7131 0.036 Uiso calc 1 . .
H H13B 0.6501 0.5604 0.7619 0.036 Uiso calc 1 . .
H H13C 0.7372 0.5424 0.6467 0.036 Uiso calc 1 . .
C C14 0.9982(4) 0.6147(4) 0.7550(4) 0.0220(8) Uani d 1 . .
H H14A 0.9986 0.5627 0.6774 0.033 Uiso calc 1 . .
H H14B 1.0871 0.6037 0.8118 0.033 Uiso calc 1 . .
H H14C 0.9954 0.7054 0.7389 0.033 Uiso calc 1 . .
C C15 0.7295(4) 0.1888(3) 0.6512(3) 0.0126(7) Uani d 1 . .
C C16 0.6071(4) 0.2444(4) 0.5922(3) 0.0137(7) Uani d 1 . .
C C17 0.6082(4) 0.2749(4) 0.4701(4) 0.0185(8) Uani d 1 . .
H H17 0.5270 0.3131 0.4291 0.022 Uiso calc 1 . .
C C18 0.7252(4) 0.2504(4) 0.4079(4) 0.0201(8) Uani d 1 . .
H H18 0.7232 0.2717 0.3252 0.024 Uiso calc 1 . .
C C19 0.8438(4) 0.1956(4) 0.4656(4) 0.0196(8) Uani d 1 . .
H H19 0.9233 0.1782 0.4226 0.023 Uiso calc 1 . .
C C20 0.8473(4) 0.1655(3) 0.5882(3) 0.0144(7) Uani d 1 . .
H H20 0.9301 0.1290 0.6286 0.017 Uiso calc 1 . .
C C21 0.4773(4) 0.2777(4) 0.6550(3) 0.0160(7) Uani d 1 . .
H H21A 0.4659 0.2181 0.7197 0.019 Uiso calc 1 . .
H H21B 0.4973 0.3659 0.6955 0.019 Uiso calc 1 . .
C C22 0.2849(4) 0.1365(4) 0.5382(4) 0.0235(9) Uani d 1 . .
H H22A 0.3601 0.0891 0.5049 0.035 Uiso calc 1 . .
H H22B 0.1973 0.1323 0.4762 0.035 Uiso calc 1 . .
H H22C 0.2596 0.0979 0.6121 0.035 Uiso calc 1 . .
C C23 0.2313(4) 0.3412(4) 0.6227(4) 0.0242(9) Uani d 1 . .
H H23A 0.1400 0.3331 0.5646 0.036 Uiso calc 1 . .
H H23B 0.2674 0.4321 0.6389 0.036 Uiso calc 1 . .
H H23C 0.2129 0.3060 0.6999 0.036 Uiso calc 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'
P P 0.1023 0.0942 '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'
Se Se -0.0929 2.2259 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 Fe1 C2 2_757 . 180.0 ?
C2 Fe1 C5 2_757 . 111.19(16) ?
C2 Fe1 C5 . . 68.81(16) ?
C2 Fe1 C5 2_757 2_757 68.81(16) ?
C2 Fe1 C5 . 2_757 111.19(16) ?
C5 Fe1 C5 . 2_757 180.0 ?
C2 Fe1 C1 2_757 2_757 40.95(14) ?
C2 Fe1 C1 . 2_757 139.05(14) ?
C5 Fe1 C1 . 2_757 138.92(14) ?
C5 Fe1 C1 2_757 2_757 41.08(14) ?
C2 Fe1 C1 2_757 . 139.05(14) ?
C2 Fe1 C1 . . 40.95(14) ?
C5 Fe1 C1 . . 41.08(14) ?
C5 Fe1 C1 2_757 . 138.92(14) ?
C1 Fe1 C1 2_757 . 180.0 ?
C2 Fe1 C3 2_757 2_757 40.27(17) ?
C2 Fe1 C3 . 2_757 139.73(17) ?
C5 Fe1 C3 . 2_757 111.82(16) ?
C5 Fe1 C3 2_757 2_757 68.18(16) ?
C1 Fe1 C3 2_757 2_757 68.21(15) ?
C1 Fe1 C3 . 2_757 111.79(15) ?
C2 Fe1 C3 2_757 . 139.73(17) ?
C2 Fe1 C3 . . 40.27(17) ?
C5 Fe1 C3 . . 68.18(16) ?
C5 Fe1 C3 2_757 . 111.82(16) ?
C1 Fe1 C3 2_757 . 111.79(15) ?
C1 Fe1 C3 . . 68.21(15) ?
C3 Fe1 C3 2_757 . 180.0 ?
C2 Fe1 C4 2_757 2_757 68.24(17) ?
C2 Fe1 C4 . 2_757 111.76(17) ?
C5 Fe1 C4 . 2_757 139.49(15) ?
C5 Fe1 C4 2_757 2_757 40.51(15) ?
C1 Fe1 C4 2_757 2_757 68.47(15) ?
C1 Fe1 C4 . 2_757 111.53(15) ?
C3 Fe1 C4 2_757 2_757 40.43(19) ?
C3 Fe1 C4 . 2_757 139.57(19) ?
C2 Fe1 C4 2_757 . 111.76(17) ?
C2 Fe1 C4 . . 68.24(17) ?
C5 Fe1 C4 . . 40.51(15) ?
C5 Fe1 C4 2_757 . 139.49(15) ?
C1 Fe1 C4 2_757 . 111.53(15) ?
C1 Fe1 C4 . . 68.47(15) ?
C3 Fe1 C4 2_757 . 139.57(19) ?
C3 Fe1 C4 . . 40.43(19) ?
C4 Fe1 C4 2_757 . 180.0 ?
C1 P1 C15 . . 106.22(16) ?
C1 P1 C6 . . 104.97(17) ?
C15 P1 C6 . . 109.45(16) ?
C1 P1 Se1 . . 113.04(12) ?
C15 P1 Se1 . . 108.10(12) ?
C6 P1 Se1 . . 114.70(12) ?
C14 N1 C12 . . 109.5(3) ?
C14 N1 C13 . . 109.7(3) ?
C12 N1 C13 . . 111.0(3) ?
C21 N2 C22 . . 110.2(3) ?
C21 N2 C23 . . 111.1(3) ?
C22 N2 C23 . . 110.1(3) ?
C2 C1 C5 . . 107.4(3) ?
C2 C1 P1 . . 124.1(3) ?
C5 C1 P1 . . 128.4(3) ?
C2 C1 Fe1 . . 69.4(2) ?
C5 C1 Fe1 . . 69.4(2) ?
P1 C1 Fe1 . . 128.89(19) ?
C3 C2 C1 . . 108.3(4) ?
C3 C2 Fe1 . . 70.7(2) ?
C1 C2 Fe1 . . 69.7(2) ?
C3 C2 H2 . . 125.9 ?
C1 C2 H2 . . 125.9 ?
Fe1 C2 H2 . . 125.4 ?
C2 C3 C4 . . 108.4(3) ?
C2 C3 Fe1 . . 69.0(2) ?
C4 C3 Fe1 . . 69.8(2) ?
C2 C3 H3 . . 125.8 ?
C4 C3 H3 . . 125.8 ?
Fe1 C3 H3 . . 126.9 ?
C5 C4 C3 . . 107.8(4) ?
C5 C4 Fe1 . . 69.0(2) ?
C3 C4 Fe1 . . 69.7(2) ?
C5 C4 H4 . . 126.1 ?
C3 C4 H4 . . 126.1 ?
Fe1 C4 H4 . . 126.8 ?
C4 C5 C1 . . 108.0(3) ?
C4 C5 Fe1 . . 70.5(2) ?
C1 C5 Fe1 . . 69.5(2) ?
C4 C5 H5 . . 126.0 ?
C1 C5 H5 . . 126.0 ?
Fe1 C5 H5 . . 125.6 ?
C11 C6 C7 . . 120.1(3) ?
C11 C6 P1 . . 114.8(3) ?
C7 C6 P1 . . 125.1(3) ?
C8 C7 C6 . . 117.5(3) ?
C8 C7 C12 . . 117.6(3) ?
C6 C7 C12 . . 124.9(3) ?
C9 C8 C7 . . 121.8(3) ?
C9 C8 H8 . . 119.1 ?
C7 C8 H8 . . 119.1 ?
C8 C9 C10 . . 120.2(3) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C11 C10 C9 . . 119.4(3) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C10 C11 C6 . . 121.0(3) ?
C10 C11 H11 . . 119.5 ?
C6 C11 H11 . . 119.5 ?
N1 C12 C7 . . 113.8(3) ?
N1 C12 H12A . . 108.8 ?
C7 C12 H12A . . 108.8 ?
N1 C12 H12B . . 108.8 ?
C7 C12 H12B . . 108.8 ?
H12A C12 H12B . . 107.7 ?
N1 C13 H13A . . 109.5 ?
N1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N1 C14 H14A . . 109.5 ?
N1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C20 C15 C16 . . 120.1(3) ?
C20 C15 P1 . . 117.9(3) ?
C16 C15 P1 . . 121.8(3) ?
C17 C16 C15 . . 118.1(3) ?
C17 C16 C21 . . 118.2(3) ?
C15 C16 C21 . . 123.6(3) ?
C18 C17 C16 . . 121.4(4) ?
C18 C17 H17 . . 119.3 ?
C16 C17 H17 . . 119.3 ?
C19 C18 C17 . . 120.2(4) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C18 C19 C20 . . 119.9(4) ?
C18 C19 H19 . . 120.1 ?
C20 C19 H19 . . 120.1 ?
C15 C20 C19 . . 120.3(3) ?
C15 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
N2 C21 C16 . . 113.0(3) ?
N2 C21 H21A . . 109.0 ?
C16 C21 H21A . . 109.0 ?
N2 C21 H21B . . 109.0 ?
C16 C21 H21B . . 109.0 ?
H21A C21 H21B . . 107.8 ?
N2 C22 H22A . . 109.5 ?
N2 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
N2 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
N2 C23 H23A . . 109.5 ?
N2 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
N2 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Se1 P1 . 2.1132(11) ?
Fe1 C2 2_757 2.047(4) ?
Fe1 C2 . 2.047(4) ?
Fe1 C5 . 2.050(4) ?
Fe1 C5 2_757 2.050(4) ?
Fe1 C1 2_757 2.050(4) ?
Fe1 C1 . 2.050(4) ?
Fe1 C3 2_757 2.069(4) ?
Fe1 C3 . 2.069(4) ?
Fe1 C4 2_757 2.071(4) ?
Fe1 C4 . 2.071(4) ?
P1 C1 . 1.796(4) ?
P1 C15 . 1.826(4) ?
P1 C6 . 1.829(4) ?
N1 C14 . 1.455(5) ?
N1 C12 . 1.466(4) ?
N1 C13 . 1.468(5) ?
N2 C21 . 1.456(5) ?
N2 C22 . 1.457(5) ?
N2 C23 . 1.458(5) ?
C1 C2 . 1.433(5) ?
C1 C5 . 1.439(5) ?
C2 C3 . 1.417(6) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.431(7) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.427(5) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 C11 . 1.397(5) ?
C6 C7 . 1.418(5) ?
C7 C8 . 1.403(5) ?
C7 C12 . 1.508(5) ?
C8 C9 . 1.386(6) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.390(5) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.388(5) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 C20 . 1.396(5) ?
C15 C16 . 1.410(5) ?
C16 C17 . 1.403(5) ?
C16 C21 . 1.516(5) ?
C17 C18 . 1.387(5) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.373(6) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.402(5) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?

_cod_database_fobs_code 2022575
