##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'from SHELXL-2014'
_journal_date_recd_electronic     2017-09-08
_journal_date_accepted     2017-09-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue     10
_journal_page_first     1539
_journal_page_last     1541
_journal_paper_category     GM
_journal_paper_doi     10.1107/S2056989017013408
_journal_coeditor_code     IM2484
_publ_contact_author_name     'Petr Stepnicka'
_publ_contact_author_address
;
Department of Inorganic Chemistry
Faculty of Science, Charles University
Hlavova 2030
128 40 Prague 2
Czech Republic
;
_publ_contact_author_email     petr.stepnicka@natur.cuni.cz
_publ_contact_author_fax     '+420 221 951 253'
_publ_contact_author_phone     '+420 221 951 260'
_publ_section_title
;
Crystal structure of {[1'-(diphenylphosphino)ferrocenyl]methyl}dimethylammonium
chloride monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Martin Zábranský' .
;
Department of Inorganic Chemistry
Faculty of Science, Charles University
Hlavova 2030
128 40 Prague 2
Czech Republic
;
    'Petr Štěpnička' .
;
Department of Inorganic Chemistry
Faculty of Science, Charles University
Hlavova 2030
128 40 Prague 2
Czech Republic
;
_publ_section_synopsis
;
The molecular structure of
{[1'-(diphenylphosphino)ferrocenyl]methyl}dimethylammonium chloride
monohydrate is presented. Individual ions and the solvating water molecule
assemble into dimeric units located around crystallographic inversion centers
via N---H...Cl and O---H...Cl hydrogen bonds.
;
data_I
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
{[1'-(Diphenylphosphino)ferrocenyl]methyl}dimethylammonium chloride
monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C25 H27 Fe N P +, Cl -, H2 O'
_chemical_formula_sum     'C25 H29 Cl Fe N O P'
_chemical_formula_iupac     '[Fe (C8 H13 N) (C17 H14 P] Cl, H2 O'
_chemical_formula_weight     481.76
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.9888(3)
_cell_length_b     12.7596(6)
_cell_length_c     13.2311(5)
_cell_angle_alpha     111.0370(10)
_cell_angle_beta     104.0750(10)
_cell_angle_gamma     99.628(2)
_cell_volume     1171.76(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9875
_cell_measurement_theta_min     2.72
_cell_measurement_theta_max     27.46
_cell_measurement_temperature     150(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.270
_exptl_crystal_size_mid     0.260
_exptl_crystal_size_min     0.140
_exptl_crystal_density_diffrn     1.365
_exptl_crystal_F_000     504
_exptl_absorpt_coefficient_mu     0.842
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.804
_shelx_estimated_absorpt_T_max     0.891
_exptl_absorpt_correction_T_min     0.78
_exptl_absorpt_correction_T_max     0.89
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator     'Quazar Mo multilayer optic'
_diffrn_measurement_device_type
                                   'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     24764
_diffrn_reflns_av_R_equivalents     0.0243
_diffrn_reflns_theta_min     2.720
_diffrn_reflns_theta_max     27.492
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     15
_reflns_number_total     5361
_reflns_number_gt     4820
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0331
_refine_ls_R_factor_gt     0.0281
_refine_ls_wR_factor_gt     0.0710
_refine_ls_wR_factor_ref     0.0735
_refine_ls_goodness_of_fit_ref     1.057
_refine_ls_restrained_S_all     1.057
_refine_ls_number_reflns     5361
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0302P)²+0.8395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.770
_refine_diff_density_min     -0.527
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'P' 'P' 0.1023 0.0942
                         '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'
    'Fe' 'Fe' 0.3463 0.8444
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
Instrument Service (Bruker, 2015)
;
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
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
    Fe Fe 0.35629(3) 0.59451(2) 0.78521(2) 0.01686(7) Uani d 1 . .
    P P 0.60918(5) 0.42728(3) 0.65913(3) 0.02008(9) Uani d 1 . .
    N N 0.48959(19) 0.94040(11) 0.77917(12) 0.0222(3) Uani d 1 . .
    H H1N 0.4115 0.9619 0.8185 0.027 Uiso d 1 . .
    C C1 0.3623(2) 0.73548(13) 0.74808(13) 0.0190(3) Uani d 1 . .
    C C2 0.3012(2) 0.63030(14) 0.64396(13) 0.0246(3) Uani d 1 . .
    H H2 0.3559 0.6120 0.5860 0.029 Uiso calc 1 . .
    C C3 0.1436(2) 0.55845(15) 0.64331(15) 0.0305(4) Uani d 1 . .
    H H3 0.0755 0.4832 0.5850 0.037 Uiso calc 1 . .
    C C4 0.1056(2) 0.61835(16) 0.74453(17) 0.0306(4) Uani d 1 . .
    H H4 0.0075 0.5903 0.7655 0.037 Uiso calc 1 . .
    C C5 0.2396(2) 0.72753(15) 0.80907(15) 0.0242(3) Uani d 1 . .
    H H5 0.2463 0.7853 0.8805 0.029 Uiso calc 1 . .
    C C6 0.5294(2) 0.49253(13) 0.77727(13) 0.0188(3) Uani d 1 . .
    C C7 0.3773(2) 0.44264(14) 0.80049(13) 0.0214(3) Uani d 1 . .
    H H7 0.2959 0.3668 0.7549 0.026 Uiso calc 1 . .
    C C8 0.3684(3) 0.52571(16) 0.90340(14) 0.0282(4) Uani d 1 . .
    H H8 0.2794 0.5153 0.9380 0.034 Uiso calc 1 . .
    C C9 0.5155(3) 0.62697(15) 0.94565(14) 0.0295(4) Uani d 1 . .
    H H9 0.5427 0.6956 1.0139 0.035 Uiso calc 1 . .
    C C10 0.6153(2) 0.60790(14) 0.86822(14) 0.0240(3) Uani d 1 . .
    H H10 0.7199 0.6617 0.8753 0.029 Uiso calc 1 . .
    C C11 0.5289(2) 0.83286(14) 0.79066(14) 0.0231(3) Uani d 1 . .
    H H11A 0.6098 0.8067 0.7468 0.028 Uiso calc 1 . .
    H H11B 0.5921 0.8529 0.8723 0.028 Uiso calc 1 . .
    C C12 0.7610(2) 0.35513(13) 0.71926(14) 0.0218(3) Uani d 1 . .
    C C13 0.8462(2) 0.28984(15) 0.64905(17) 0.0315(4) Uani d 1 . .
    H H13 0.8258 0.2852 0.5736 0.038 Uiso calc 1 . .
    C C14 0.9599(2) 0.23210(16) 0.6890(2) 0.0422(5) Uani d 1 . .
    H H14 1.0132 0.1856 0.6396 0.051 Uiso calc 1 . .
    C C15 0.9964(3) 0.24150(17) 0.7998(2) 0.0442(6) Uani d 1 . .
    H H15 1.0754 0.2022 0.8268 0.053 Uiso calc 1 . .
    C C16 0.9178(3) 0.30812(18) 0.8711(2) 0.0395(5) Uani d 1 . .
    H H16 0.9444 0.3160 0.9479 0.047 Uiso calc 1 . .
    C C17 0.7991(2) 0.36410(16) 0.83049(16) 0.0290(4) Uani d 1 . .
    H H17 0.7439 0.4088 0.8797 0.035 Uiso calc 1 . .
    C C18 0.4138(2) 0.30073(13) 0.56095(13) 0.0194(3) Uani d 1 . .
    C C19 0.2952(2) 0.31205(15) 0.47127(14) 0.0257(3) Uani d 1 . .
    H H19 0.3154 0.3842 0.4641 0.031 Uiso calc 1 . .
    C C20 0.1473(2) 0.21872(16) 0.39223(15) 0.0303(4) Uani d 1 . .
    H H20 0.0669 0.2278 0.3321 0.036 Uiso calc 1 . .
    C C21 0.1172(2) 0.11288(16) 0.40097(15) 0.0293(4) Uani d 1 . .
    H H21 0.0170 0.0491 0.3465 0.035 Uiso calc 1 . .
    C C22 0.2337(2) 0.10042(15) 0.48951(15) 0.0298(4) Uani d 1 . .
    H H22 0.2135 0.0278 0.4957 0.036 Uiso calc 1 . .
    C C23 0.3807(2) 0.19393(14) 0.56956(14) 0.0249(3) Uani d 1 . .
    H H23 0.4590 0.1848 0.6306 0.030 Uiso calc 1 . .
    C C24 0.3962(3) 0.91775(17) 0.65899(16) 0.0363(4) Uani d 1 . .
    H H24A 0.3688 0.9890 0.6563 0.054 Uiso calc 1 . .
    H H24B 0.2841 0.8547 0.6282 0.054 Uiso calc 1 . .
    H H24C 0.4738 0.8945 0.6128 0.054 Uiso calc 1 . .
    C C25 0.6568(3) 1.03899(16) 0.83233(19) 0.0405(5) Uani d 1 . .
    H H25A 0.7412 1.0191 0.7907 0.061 Uiso calc 1 . .
    H H25B 0.7117 1.0534 0.9126 0.061 Uiso calc 1 . .
    H H25C 0.6277 1.1095 0.8288 0.061 Uiso calc 1 . .
    Cl Cl 0.23009(6) 1.03869(4) 0.89357(4) 0.02978(10) Uani d 1 . .
    O O1W 0.0368(2) 1.16218(15) 1.07177(16) 0.0569(4) Uani d 1 . .
    H H2W -0.0268 1.1016 1.0938 0.068 Uiso d 1 . .
    H H1W 0.0973 1.1233 1.0189 0.068 Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Fe C1 . 2.0239(15) ?
    Fe C5 . 2.0341(16) ?
    Fe C10 . 2.0389(16) ?
    Fe C8 . 2.0411(16) ?
    Fe C9 . 2.0433(16) ?
    Fe C2 . 2.0433(16) ?
    Fe C4 . 2.0469(17) ?
    Fe C3 . 2.0472(16) ?
    Fe C6 . 2.0472(15) ?
    Fe C7 . 2.0489(15) ?
    P C6 . 1.8084(16) ?
    P C12 . 1.8390(17) ?
    P C18 . 1.8427(16) ?
    N C24 . 1.480(2) ?
    N C25 . 1.485(2) ?
    N C11 . 1.508(2) ?
    N H1N . 0.9207 ?
    C1 C5 . 1.426(2) ?
    C1 C2 . 1.437(2) ?
    C1 C11 . 1.487(2) ?
    C2 C3 . 1.424(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.418(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.421(2) ?
    C4 H4 . 0.9500 ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.428(2) ?
    C6 C10 . 1.440(2) ?
    C7 C8 . 1.421(2) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.420(3) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.424(3) ?
    C9 H9 . 0.9500 ?
    C10 H10 . 0.9500 ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C17 . 1.386(2) ?
    C12 C13 . 1.401(2) ?
    C13 C14 . 1.384(3) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.380(3) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.377(3) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.397(2) ?
    C16 H16 . 0.9500 ?
    C17 H17 . 0.9500 ?
    C18 C23 . 1.395(2) ?
    C18 C19 . 1.396(2) ?
    C19 C20 . 1.393(2) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.383(3) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.385(2) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.394(2) ?
    C22 H22 . 0.9500 ?
    C23 H23 . 0.9500 ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 0.9800 ?
    C25 H25A . 0.9800 ?
    C25 H25B . 0.9800 ?
    C25 H25C . 0.9800 ?
    O1W H2W . 1.0206 ?
    O1W H1W . 0.9824 ?
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
    C1 Fe C5 . . 41.14(6) ?
    C1 Fe C10 . . 106.92(7) ?
    C5 Fe C10 . . 126.23(7) ?
    C1 Fe C8 . . 148.86(7) ?
    C5 Fe C8 . . 115.03(7) ?
    C10 Fe C8 . . 68.79(7) ?
    C1 Fe C9 . . 115.70(7) ?
    C5 Fe C9 . . 104.86(7) ?
    C10 Fe C9 . . 40.82(7) ?
    C8 Fe C9 . . 40.70(8) ?
    C1 Fe C2 . . 41.36(6) ?
    C5 Fe C2 . . 69.00(7) ?
    C10 Fe C2 . . 119.30(7) ?
    C8 Fe C2 . . 167.52(7) ?
    C9 Fe C2 . . 151.52(8) ?
    C1 Fe C4 . . 69.01(7) ?
    C5 Fe C4 . . 40.74(7) ?
    C10 Fe C4 . . 163.98(7) ?
    C8 Fe C4 . . 106.22(8) ?
    C9 Fe C4 . . 125.71(8) ?
    C2 Fe C4 . . 68.59(7) ?
    C1 Fe C3 . . 69.10(6) ?
    C5 Fe C3 . . 68.56(7) ?
    C10 Fe C3 . . 154.05(8) ?
    C8 Fe C3 . . 128.15(8) ?
    C9 Fe C3 . . 164.68(8) ?
    C2 Fe C3 . . 40.75(7) ?
    C4 Fe C3 . . 40.52(8) ?
    C1 Fe C6 . . 129.28(6) ?
    C5 Fe C6 . . 166.26(7) ?
    C10 Fe C6 . . 41.28(6) ?
    C8 Fe C6 . . 68.83(7) ?
    C9 Fe C6 . . 68.93(6) ?
    C2 Fe C6 . . 110.24(7) ?
    C4 Fe C6 . . 152.74(7) ?
    C3 Fe C6 . . 120.44(7) ?
    C1 Fe C7 . . 168.72(6) ?
    C5 Fe C7 . . 149.81(7) ?
    C10 Fe C7 . . 68.83(7) ?
    C8 Fe C7 . . 40.66(6) ?
    C9 Fe C7 . . 68.44(7) ?
    C2 Fe C7 . . 130.66(6) ?
    C4 Fe C7 . . 117.98(7) ?
    C3 Fe C7 . . 109.84(7) ?
    C6 Fe C7 . . 40.81(6) ?
    C6 P C12 . . 100.79(7) ?
    C6 P C18 . . 101.23(7) ?
    C12 P C18 . . 100.82(7) ?
    C24 N C25 . . 111.96(15) ?
    C24 N C11 . . 112.50(13) ?
    C25 N C11 . . 110.50(14) ?
    C24 N H1N . . 105.9 ?
    C25 N H1N . . 107.8 ?
    C11 N H1N . . 107.9 ?
    C5 C1 C2 . . 107.59(15) ?
    C5 C1 C11 . . 124.99(15) ?
    C2 C1 C11 . . 127.30(15) ?
    C5 C1 Fe . . 69.82(9) ?
    C2 C1 Fe . . 70.04(9) ?
    C11 C1 Fe . . 122.55(11) ?
    C3 C2 C1 . . 107.63(15) ?
    C3 C2 Fe . . 69.77(9) ?
    C1 C2 Fe . . 68.59(9) ?
    C3 C2 H2 . . 126.2 ?
    C1 C2 H2 . . 126.2 ?
    Fe C2 H2 . . 127.0 ?
    C4 C3 C2 . . 108.37(15) ?
    C4 C3 Fe . . 69.73(10) ?
    C2 C3 Fe . . 69.48(9) ?
    C4 C3 H3 . . 125.8 ?
    C2 C3 H3 . . 125.8 ?
    Fe C3 H3 . . 126.6 ?
    C3 C4 C5 . . 108.16(16) ?
    C3 C4 Fe . . 69.75(10) ?
    C5 C4 Fe . . 69.14(9) ?
    C3 C4 H4 . . 125.9 ?
    C5 C4 H4 . . 125.9 ?
    Fe C4 H4 . . 126.8 ?
    C4 C5 C1 . . 108.24(15) ?
    C4 C5 Fe . . 70.11(10) ?
    C1 C5 Fe . . 69.05(9) ?
    C4 C5 H5 . . 125.9 ?
    C1 C5 H5 . . 125.9 ?
    Fe C5 H5 . . 126.5 ?
    C7 C6 C10 . . 107.30(14) ?
    C7 C6 P . . 128.31(12) ?
    C10 C6 P . . 124.39(13) ?
    C7 C6 Fe . . 69.66(9) ?
    C10 C6 Fe . . 69.05(8) ?
    P C6 Fe . . 127.25(8) ?
    C8 C7 C6 . . 108.38(15) ?
    C8 C7 Fe . . 69.38(9) ?
    C6 C7 Fe . . 69.53(8) ?
    C8 C7 H7 . . 125.8 ?
    C6 C7 H7 . . 125.8 ?
    Fe C7 H7 . . 126.9 ?
    C9 C8 C7 . . 108.19(15) ?
    C9 C8 Fe . . 69.73(9) ?
    C7 C8 Fe . . 69.97(9) ?
    C9 C8 H8 . . 125.9 ?
    C7 C8 H8 . . 125.9 ?
    Fe C8 H8 . . 126.0 ?
    C8 C9 C10 . . 108.27(15) ?
    C8 C9 Fe . . 69.57(9) ?
    C10 C9 Fe . . 69.43(9) ?
    C8 C9 H9 . . 125.9 ?
    C10 C9 H9 . . 125.9 ?
    Fe C9 H9 . . 126.7 ?
    C9 C10 C6 . . 107.85(15) ?
    C9 C10 Fe . . 69.75(9) ?
    C6 C10 Fe . . 69.67(9) ?
    C9 C10 H10 . . 126.1 ?
    C6 C10 H10 . . 126.1 ?
    Fe C10 H10 . . 126.1 ?
    C1 C11 N . . 112.09(13) ?
    C1 C11 H11A . . 109.2 ?
    N C11 H11A . . 109.2 ?
    C1 C11 H11B . . 109.2 ?
    N C11 H11B . . 109.2 ?
    H11A C11 H11B . . 107.9 ?
    C17 C12 C13 . . 118.37(16) ?
    C17 C12 P . . 123.83(13) ?
    C13 C12 P . . 117.78(14) ?
    C14 C13 C12 . . 120.41(19) ?
    C14 C13 H13 . . 119.8 ?
    C12 C13 H13 . . 119.8 ?
    C15 C14 C13 . . 120.62(19) ?
    C15 C14 H14 . . 119.7 ?
    C13 C14 H14 . . 119.7 ?
    C16 C15 C14 . . 119.70(18) ?
    C16 C15 H15 . . 120.1 ?
    C14 C15 H15 . . 120.1 ?
    C15 C16 C17 . . 120.0(2) ?
    C15 C16 H16 . . 120.0 ?
    C17 C16 H16 . . 120.0 ?
    C12 C17 C16 . . 120.80(18) ?
    C12 C17 H17 . . 119.6 ?
    C16 C17 H17 . . 119.6 ?
    C23 C18 C19 . . 118.43(15) ?
    C23 C18 P . . 123.76(12) ?
    C19 C18 P . . 117.78(12) ?
    C20 C19 C18 . . 120.71(16) ?
    C20 C19 H19 . . 119.6 ?
    C18 C19 H19 . . 119.6 ?
    C21 C20 C19 . . 120.27(16) ?
    C21 C20 H20 . . 119.9 ?
    C19 C20 H20 . . 119.9 ?
    C20 C21 C22 . . 119.64(16) ?
    C20 C21 H21 . . 120.2 ?
    C22 C21 H21 . . 120.2 ?
    C21 C22 C23 . . 120.31(16) ?
    C21 C22 H22 . . 119.8 ?
    C23 C22 H22 . . 119.8 ?
    C22 C23 C18 . . 120.63(15) ?
    C22 C23 H23 . . 119.7 ?
    C18 C23 H23 . . 119.7 ?
    N C24 H24A . . 109.5 ?
    N C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    N C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    N C25 H25A . . 109.5 ?
    N C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    N C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    H2W O1W H1W . . 107.9 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 C1 C2 C3 . . . . -0.93(17) ?
    C11 C1 C2 C3 . . . . 175.34(14) ?
    Fe C1 C2 C3 . . . . 59.05(11) ?
    C5 C1 C2 Fe . . . . -59.99(11) ?
    C11 C1 C2 Fe . . . . 116.29(15) ?
    C1 C2 C3 C4 . . . . 0.75(18) ?
    Fe C2 C3 C4 . . . . 59.06(12) ?
    C1 C2 C3 Fe . . . . -58.32(10) ?
    C2 C3 C4 C5 . . . . -0.27(19) ?
    Fe C3 C4 C5 . . . . 58.64(11) ?
    C2 C3 C4 Fe . . . . -58.91(11) ?
    C3 C4 C5 C1 . . . . -0.31(18) ?
    Fe C4 C5 C1 . . . . 58.70(11) ?
    C3 C4 C5 Fe . . . . -59.01(12) ?
    C2 C1 C5 C4 . . . . 0.77(17) ?
    C11 C1 C5 C4 . . . . -175.61(14) ?
    Fe C1 C5 C4 . . . . -59.36(11) ?
    C2 C1 C5 Fe . . . . 60.13(10) ?
    C11 C1 C5 Fe . . . . -116.26(15) ?
    C12 P C6 C7 . . . . -89.13(14) ?
    C18 P C6 C7 . . . . 14.33(15) ?
    C12 P C6 C10 . . . . 89.71(13) ?
    C18 P C6 C10 . . . . -166.83(13) ?
    C12 P C6 Fe . . . . 178.35(9) ?
    C18 P C6 Fe . . . . -78.20(11) ?
    C10 C6 C7 C8 . . . . 0.36(17) ?
    P C6 C7 C8 . . . . 179.36(12) ?
    Fe C6 C7 C8 . . . . -58.65(11) ?
    C10 C6 C7 Fe . . . . 59.01(10) ?
    P C6 C7 Fe . . . . -121.99(12) ?
    C6 C7 C8 C9 . . . . -0.73(18) ?
    Fe C7 C8 C9 . . . . -59.47(11) ?
    C6 C7 C8 Fe . . . . 58.75(11) ?
    C7 C8 C9 C10 . . . . 0.81(18) ?
    Fe C8 C9 C10 . . . . -58.81(11) ?
    C7 C8 C9 Fe . . . . 59.62(11) ?
    C8 C9 C10 C6 . . . . -0.58(18) ?
    Fe C9 C10 C6 . . . . -59.48(10) ?
    C8 C9 C10 Fe . . . . 58.89(11) ?
    C7 C6 C10 C9 . . . . 0.14(17) ?
    P C6 C10 C9 . . . . -178.91(11) ?
    Fe C6 C10 C9 . . . . 59.53(11) ?
    C7 C6 C10 Fe . . . . -59.39(10) ?
    P C6 C10 Fe . . . . 121.56(11) ?
    C5 C1 C11 N . . . . -77.55(19) ?
    C2 C1 C11 N . . . . 106.78(17) ?
    Fe C1 C11 N . . . . -164.53(10) ?
    C24 N C11 C1 . . . . -59.33(18) ?
    C25 N C11 C1 . . . . 174.72(14) ?
    C6 P C12 C17 . . . . -3.86(16) ?
    C18 P C12 C17 . . . . -107.64(15) ?
    C6 P C12 C13 . . . . 177.80(13) ?
    C18 P C12 C13 . . . . 74.02(14) ?
    C17 C12 C13 C14 . . . . 2.5(2) ?
    P C12 C13 C14 . . . . -179.02(14) ?
    C12 C13 C14 C15 . . . . -2.5(3) ?
    C13 C14 C15 C16 . . . . 0.6(3) ?
    C14 C15 C16 C17 . . . . 1.2(3) ?
    C13 C12 C17 C16 . . . . -0.8(3) ?
    P C12 C17 C16 . . . . -179.14(14) ?
    C15 C16 C17 C12 . . . . -1.0(3) ?
    C6 P C18 C23 . . . . -83.71(15) ?
    C12 P C18 C23 . . . . 19.72(15) ?
    C6 P C18 C19 . . . . 97.97(13) ?
    C12 P C18 C19 . . . . -158.60(13) ?
    C23 C18 C19 C20 . . . . -0.1(2) ?
    P C18 C19 C20 . . . . 178.34(13) ?
    C18 C19 C20 C21 . . . . -0.7(3) ?
    C19 C20 C21 C22 . . . . 0.7(3) ?
    C20 C21 C22 C23 . . . . 0.1(3) ?
    C21 C22 C23 C18 . . . . -0.8(3) ?
    C19 C18 C23 C22 . . . . 0.8(3) ?
    P C18 C23 C22 . . . . -177.51(14) ?
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
    N H1N Cl 1_555 0.92 2.13 3.0323(16) 167
    O1W H1W Cl 1_555 0.98 2.23 3.2162(19) 177
    O1W H2W Cl 2_577 1.02 2.29 3.289(2) 166
    C10 H10 O1W 2_677 0.95 2.46 3.390(3) 165
    C11 H11B Cl 2_677 0.99 2.77 3.7369(17) 167
