##############################################################################
#                                                                            #
# 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.                                        #
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##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1020729'
_audit_creation_method     SHELXL-2013
_journal_date_recd_electronic     2014-08-18
_journal_date_accepted     2014-08-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      9
_journal_page_first     148
_journal_page_last     152
_journal_paper_category     GM
_journal_paper_doi     10.1107/S1600536814019072
_journal_coeditor_code     WM5051
_publ_contact_author_name     'Timothy John Prior'
_publ_contact_author_address
;
Chemistry
University of Hull
Cottingham Road
Hull HU6 7RX
England
;
_publ_contact_author_email     't.prior@hull.ac.uk'
_publ_contact_author_fax     '+44 (0) 1482 466410'
_publ_contact_author_phone     '+44 (0)1482 466389'
_publ_section_title
;
Crystal structures of two cross-bridged chromium(III) tetraazamacrocycles
;
loop_
    _publ_author_name
    _publ_author_address
    'Prior, Timothy J.'
;
Department of Chemistry
University of Hull
Cottingham Road
Hull HU6 7RX
England
;
    'Maples, Danny L.'
;
Department of Chemistry and Physics
Southwestern Oklahoma State University
Weatherford
OK 73096
USA
;
    'Maples, Randall D.'
;
Department of Chemistry and Physics
Southwestern Oklahoma State University
Weatherford
OK 73096
USA
;
    'Hoffert, Wesley A.'
;
Department of Natural Science
McPherson College
McPherson
KS 67460
USA
;
    'Parsell, Trenton H.'
;
Department of Natural Science
McPherson College
McPherson
KS 67460
USA
;
    'Silversides, Jon D.'
;
Department of Chemistry
University of Hull
Cottingham Road
Hull HU6 7RX
England
;
    'Archibald, Stephen J.'
;
Department of Chemistry
University of Hull
Cottingham Road
Hull HU6 7RX
England
;
    'Hubin, Timothy J.'
;
Department of Chemistry and Physics
Southwestern Oklahoma State University
Weatherford
OK 73096
USA
;
_publ_section_synopsis
;
Chromium(III) complexes of two ethylene cross-bridged tetraazamacrocycles were
prepared and structurally characterized in order to extend the coordination
chemistry of this ligand type farther towards the early transition metals.
;
_chemical_name_systematic
;\
Dichlorido(4,10-dimethyl-1,4,7,10-tetraazabicyclo[5.5.2]tetradecane)\
chromium(III) hexafluoridophosphate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H26 Cl2 Cr N4 +, F6 P -'
_chemical_formula_sum     'C12 H26 Cl2 Cr F6 N4 P'
_chemical_formula_iupac     '[Cr Cl2 (C12 H26 N4)] P F6'
_chemical_formula_weight     494.24
_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     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.2271(10)
_cell_length_b     19.957(2)
_cell_length_c     12.0474(17)
_cell_angle_alpha     90
_cell_angle_beta     96.374(11)
_cell_angle_gamma     90
_cell_volume     1965.8(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     12040
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     31.20
_cell_measurement_temperature     150(2)
_exptl_crystal_description     block
_exptl_crystal_colour     purple
_exptl_crystal_size_max     0.100
_exptl_crystal_size_mid     0.100
_exptl_crystal_size_min     0.080
_exptl_crystal_density_diffrn     1.670
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1012
_exptl_absorpt_coefficient_mu     0.995
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details
;
[a face-indexed absorption correction was applied;
X-AREA (Stoe & Cie, 2002)]
;
_shelx_estimated_absorpt_T_min     0.907
_shelx_estimated_absorpt_T_max     0.925
_exptl_absorpt_correction_T_min     0.8267
_exptl_absorpt_correction_T_max     0.9154
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Stoe IPDS2'
_diffrn_measurement_method     'ω-scans'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     22999
_diffrn_reflns_av_R_equivalents     0.0905
_diffrn_reflns_theta_min     2.657
_diffrn_reflns_theta_max     27.499
_diffrn_reflns_theta_full     25.000
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
;
_reflns_number_total     4501
_reflns_number_gt     2798
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0788
_refine_ls_R_factor_gt     0.0405
_refine_ls_wR_factor_gt     0.0864
_refine_ls_wR_factor_ref     0.0963
_refine_ls_goodness_of_fit_ref     0.879
_refine_ls_restrained_S_all     0.879
_refine_ls_number_reflns     4501
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0474P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.768
_refine_diff_density_min     -0.493
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cr' 'Cr' 0.3209 0.6236
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         '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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction     'X-AREA (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS86 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL2013 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    Cr Cr1 0.21553(5) 0.19169(2) 0.20979(4) 0.02173(12) Uani d 1 . .
    Cl Cl1 -0.06600(7) 0.20275(4) 0.17145(7) 0.03159(19) Uani d 1 . .
    Cl Cl2 0.25268(8) 0.23403(4) 0.03552(7) 0.03325(19) Uani d 1 . .
    N N1 0.2035(3) 0.15406(14) 0.3675(2) 0.0274(6) Uani d 1 . .
    N N2 0.2399(3) 0.09097(13) 0.1641(2) 0.0276(6) Uani d 1 . .
    N N3 0.4628(3) 0.18082(13) 0.2517(2) 0.0234(5) Uani d 1 . .
    N N4 0.2408(3) 0.28159(14) 0.2997(2) 0.0296(6) Uani d 1 . .
    C C1 0.1252(4) 0.08715(17) 0.3466(3) 0.0348(8) Uani d 1 . .
    H H1A 0.0099 0.0927 0.3144 0.042 Uiso calc 1 . .
    H H1B 0.1267 0.0621 0.4177 0.042 Uiso calc 1 . .
    C C2 0.2193(4) 0.04929(17) 0.2664(3) 0.0340(7) Uani d 1 . .
    H H2A 0.1606 0.0074 0.2435 0.041 Uiso calc 1 . .
    H H2B 0.3283 0.0371 0.3042 0.041 Uiso calc 1 . .
    C C3 0.4087(3) 0.08276(17) 0.1267(3) 0.0328(8) Uani d 1 . .
    H H3A 0.3976 0.0776 0.0445 0.039 Uiso calc 1 . .
    H H3B 0.4586 0.0412 0.1599 0.039 Uiso calc 1 . .
    C C4 0.5235(3) 0.14187(17) 0.1595(3) 0.0300(7) Uani d 1 . .
    H H4A 0.6348 0.1249 0.1837 0.036 Uiso calc 1 . .
    H H4B 0.5296 0.1714 0.0940 0.036 Uiso calc 1 . .
    C C5 0.5233(3) 0.25153(16) 0.2599(3) 0.0298(7) Uani d 1 . .
    H H5A 0.5118 0.2726 0.1850 0.036 Uiso calc 1 . .
    H H5B 0.6402 0.2524 0.2899 0.036 Uiso calc 1 . .
    C C6 0.4221(3) 0.28971(17) 0.3373(3) 0.0325(8) Uani d 1 . .
    H H6A 0.4467 0.2726 0.4145 0.039 Uiso calc 1 . .
    H H6B 0.4515 0.3378 0.3372 0.039 Uiso calc 1 . .
    C C7 0.1464(4) 0.27476(19) 0.3992(3) 0.0370(8) Uani d 1 . .
    H H7A 0.0446 0.3014 0.3858 0.044 Uiso calc 1 . .
    H H7B 0.2124 0.2937 0.4655 0.044 Uiso calc 1 . .
    C C8 0.1016(4) 0.20179(19) 0.4244(3) 0.0379(8) Uani d 1 . .
    H H8A 0.1186 0.1940 0.5061 0.045 Uiso calc 1 . .
    H H8B -0.0154 0.1939 0.3988 0.045 Uiso calc 1 . .
    C C9 0.3681(3) 0.14731(18) 0.4344(3) 0.0321(7) Uani d 1 . .
    H H9A 0.3697 0.1062 0.4805 0.038 Uiso calc 1 . .
    H H9B 0.3867 0.1861 0.4854 0.038 Uiso calc 1 . .
    C C10 0.5051(3) 0.14384(16) 0.3594(3) 0.0275(7) Uani d 1 . .
    H H10A 0.6059 0.1633 0.3993 0.033 Uiso calc 1 . .
    H H10B 0.5276 0.0963 0.3429 0.033 Uiso calc 1 . .
    C C11 0.1158(4) 0.06839(19) 0.0721(3) 0.0377(8) Uani d 1 . .
    H H11A 0.0059 0.0742 0.0947 0.057 Uiso calc 1 . .
    H H11B 0.1338 0.0210 0.0559 0.057 Uiso calc 1 . .
    H H11C 0.1262 0.0951 0.0050 0.057 Uiso calc 1 . .
    C C12 0.1830(4) 0.34219(19) 0.2353(4) 0.0428(9) Uani d 1 . .
    H H12A 0.0660 0.3378 0.2103 0.064 Uiso calc 1 . .
    H H12B 0.2437 0.3469 0.1701 0.064 Uiso calc 1 . .
    H H12C 0.2012 0.3819 0.2829 0.064 Uiso calc 1 . .
    P P1 0.74031(9) 0.44740(4) 0.22662(7) 0.0291(2) Uani d 1 . .
    F F1 0.8570(3) 0.43093(16) 0.3353(2) 0.0756(8) Uani d 1 . .
    F F2 0.8987(2) 0.46269(12) 0.1662(2) 0.0570(6) Uani d 1 . .
    F F3 0.6248(3) 0.46395(16) 0.1167(2) 0.0744(8) Uani d 1 . .
    F F4 0.5828(3) 0.43324(12) 0.2878(2) 0.0604(7) Uani d 1 . .
    F F5 0.7476(3) 0.37224(11) 0.1869(3) 0.0675(8) Uani d 1 . .
    F F6 0.7324(3) 0.52314(12) 0.2644(3) 0.0639(7) Uani d 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Cr1 N3 . 2.053(2) ?
    Cr1 N1 . 2.056(3) ?
    Cr1 N4 . 2.094(3) ?
    Cr1 N2 . 2.100(3) ?
    Cr1 Cl2 . 2.3147(9) ?
    Cr1 Cl1 . 2.3215(8) ?
    N1 C8 . 1.486(4) ?
    N1 C1 . 1.492(4) ?
    N1 C9 . 1.503(4) ?
    N2 C11 . 1.491(4) ?
    N2 C2 . 1.512(4) ?
    N2 C3 . 1.516(3) ?
    N3 C4 . 1.486(4) ?
    N3 C5 . 1.496(4) ?
    N3 C10 . 1.499(4) ?
    N4 C12 . 1.486(5) ?
    N4 C7 . 1.505(4) ?
    N4 C6 . 1.519(4) ?
    C1 C2 . 1.507(5) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.535(5) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.522(4) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.541(5) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.523(4) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    P1 F1 . 1.570(3) ?
    P1 F3 . 1.577(3) ?
    P1 F5 . 1.578(2) ?
    P1 F6 . 1.582(2) ?
    P1 F4 . 1.585(2) ?
    P1 F2 . 1.591(2) ?
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
    N3 Cr1 N1 . . 83.23(10) ?
    N3 Cr1 N4 . . 85.68(10) ?
    N1 Cr1 N4 . . 81.21(11) ?
    N3 Cr1 N2 . . 80.93(9) ?
    N1 Cr1 N2 . . 84.74(11) ?
    N4 Cr1 N2 . . 161.62(11) ?
    N3 Cr1 Cl2 . . 91.97(7) ?
    N1 Cr1 Cl2 . . 175.19(7) ?
    N4 Cr1 Cl2 . . 98.09(8) ?
    N2 Cr1 Cl2 . . 94.91(8) ?
    N3 Cr1 Cl1 . . 177.18(8) ?
    N1 Cr1 Cl1 . . 93.99(7) ?
    N4 Cr1 Cl1 . . 93.50(7) ?
    N2 Cr1 Cl1 . . 99.27(7) ?
    Cl2 Cr1 Cl1 . . 90.81(3) ?
    C8 N1 C1 . . 113.3(2) ?
    C8 N1 C9 . . 109.3(3) ?
    C1 N1 C9 . . 110.9(3) ?
    C8 N1 Cr1 . . 106.2(2) ?
    C1 N1 Cr1 . . 103.6(2) ?
    C9 N1 Cr1 . . 113.31(17) ?
    C11 N2 C2 . . 108.1(2) ?
    C11 N2 C3 . . 108.7(2) ?
    C2 N2 C3 . . 111.8(2) ?
    C11 N2 Cr1 . . 114.0(2) ?
    C2 N2 Cr1 . . 106.88(19) ?
    C3 N2 Cr1 . . 107.38(18) ?
    C4 N3 C5 . . 114.0(2) ?
    C4 N3 C10 . . 108.9(2) ?
    C5 N3 C10 . . 111.3(2) ?
    C4 N3 Cr1 . . 106.11(18) ?
    C5 N3 Cr1 . . 103.27(17) ?
    C10 N3 Cr1 . . 113.16(16) ?
    C12 N4 C7 . . 109.0(3) ?
    C12 N4 C6 . . 108.4(2) ?
    C7 N4 C6 . . 110.4(3) ?
    C12 N4 Cr1 . . 114.8(2) ?
    C7 N4 Cr1 . . 107.7(2) ?
    C6 N4 Cr1 . . 106.47(18) ?
    N1 C1 C2 . . 108.3(2) ?
    N1 C1 H1A . . 110.0 ?
    C2 C1 H1A . . 110.0 ?
    N1 C1 H1B . . 110.0 ?
    C2 C1 H1B . . 110.0 ?
    H1A C1 H1B . . 108.4 ?
    C1 C2 N2 . . 111.0(3) ?
    C1 C2 H2A . . 109.4 ?
    N2 C2 H2A . . 109.4 ?
    C1 C2 H2B . . 109.4 ?
    N2 C2 H2B . . 109.4 ?
    H2A C2 H2B . . 108.0 ?
    N2 C3 C4 . . 113.5(2) ?
    N2 C3 H3A . . 108.9 ?
    C4 C3 H3A . . 108.9 ?
    N2 C3 H3B . . 108.9 ?
    C4 C3 H3B . . 108.9 ?
    H3A C3 H3B . . 107.7 ?
    N3 C4 C3 . . 110.3(2) ?
    N3 C4 H4A . . 109.6 ?
    C3 C4 H4A . . 109.6 ?
    N3 C4 H4B . . 109.6 ?
    C3 C4 H4B . . 109.6 ?
    H4A C4 H4B . . 108.1 ?
    N3 C5 C6 . . 108.2(2) ?
    N3 C5 H5A . . 110.1 ?
    C6 C5 H5A . . 110.1 ?
    N3 C5 H5B . . 110.1 ?
    C6 C5 H5B . . 110.1 ?
    H5A C5 H5B . . 108.4 ?
    N4 C6 C5 . . 110.5(3) ?
    N4 C6 H6A . . 109.6 ?
    C5 C6 H6A . . 109.6 ?
    N4 C6 H6B . . 109.6 ?
    C5 C6 H6B . . 109.6 ?
    H6A C6 H6B . . 108.1 ?
    N4 C7 C8 . . 113.5(3) ?
    N4 C7 H7A . . 108.9 ?
    C8 C7 H7A . . 108.9 ?
    N4 C7 H7B . . 108.9 ?
    C8 C7 H7B . . 108.9 ?
    H7A C7 H7B . . 107.7 ?
    N1 C8 C7 . . 110.8(2) ?
    N1 C8 H8A . . 109.5 ?
    C7 C8 H8A . . 109.5 ?
    N1 C8 H8B . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 108.1 ?
    N1 C9 C10 . . 111.6(3) ?
    N1 C9 H9A . . 109.3 ?
    C10 C9 H9A . . 109.3 ?
    N1 C9 H9B . . 109.3 ?
    C10 C9 H9B . . 109.3 ?
    H9A C9 H9B . . 108.0 ?
    N3 C10 C9 . . 112.0(2) ?
    N3 C10 H10A . . 109.2 ?
    C9 C10 H10A . . 109.2 ?
    N3 C10 H10B . . 109.2 ?
    C9 C10 H10B . . 109.2 ?
    H10A C10 H10B . . 107.9 ?
    N2 C11 H11A . . 109.5 ?
    N2 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N2 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N4 C12 H12A . . 109.5 ?
    N4 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    N4 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    F1 P1 F3 . . 179.36(15) ?
    F1 P1 F5 . . 90.78(16) ?
    F3 P1 F5 . . 89.08(17) ?
    F1 P1 F6 . . 90.07(16) ?
    F3 P1 F6 . . 90.06(16) ?
    F5 P1 F6 . . 179.05(17) ?
    F1 P1 F4 . . 91.76(15) ?
    F3 P1 F4 . . 88.88(15) ?
    F5 P1 F4 . . 91.85(13) ?
    F6 P1 F4 . . 88.55(13) ?
    F1 P1 F2 . . 88.05(14) ?
    F3 P1 F2 . . 91.32(15) ?
    F5 P1 F2 . . 89.00(12) ?
    F6 P1 F2 . . 90.60(13) ?
    F4 P1 F2 . . 179.13(14) ?
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
    C8 N1 C1 C2 . . . . 167.0(3) ?
    C9 N1 C1 C2 . . . . -69.6(3) ?
    Cr1 N1 C1 C2 . . . . 52.3(3) ?
    N1 C1 C2 N2 . . . . -51.4(3) ?
    C11 N2 C2 C1 . . . . -100.3(3) ?
    C3 N2 C2 C1 . . . . 140.1(3) ?
    Cr1 N2 C2 C1 . . . . 22.8(3) ?
    C11 N2 C3 C4 . . . . 138.1(3) ?
    C2 N2 C3 C4 . . . . -102.6(3) ?
    Cr1 N2 C3 C4 . . . . 14.3(3) ?
    C5 N3 C4 C3 . . . . -157.4(3) ?
    C10 N3 C4 C3 . . . . 77.6(3) ?
    Cr1 N3 C4 C3 . . . . -44.5(3) ?
    N2 C3 C4 N3 . . . . 19.5(4) ?
    C4 N3 C5 C6 . . . . 166.7(3) ?
    C10 N3 C5 C6 . . . . -69.7(3) ?
    Cr1 N3 C5 C6 . . . . 52.0(3) ?
    C12 N4 C6 C5 . . . . -99.2(3) ?
    C7 N4 C6 C5 . . . . 141.4(3) ?
    Cr1 N4 C6 C5 . . . . 24.8(3) ?
    N3 C5 C6 N4 . . . . -52.8(3) ?
    C12 N4 C7 C8 . . . . 140.9(3) ?
    C6 N4 C7 C8 . . . . -100.1(3) ?
    Cr1 N4 C7 C8 . . . . 15.7(3) ?
    C1 N1 C8 C7 . . . . -155.4(3) ?
    C9 N1 C8 C7 . . . . 80.4(3) ?
    Cr1 N1 C8 C7 . . . . -42.3(3) ?
    N4 C7 C8 N1 . . . . 17.3(4) ?
    C8 N1 C9 C10 . . . . -140.2(3) ?
    C1 N1 C9 C10 . . . . 94.1(3) ?
    Cr1 N1 C9 C10 . . . . -21.9(3) ?
    C4 N3 C10 C9 . . . . -140.6(3) ?
    C5 N3 C10 C9 . . . . 92.9(3) ?
    Cr1 N3 C10 C9 . . . . -22.9(3) ?
    N1 C9 C10 N3 . . . . 28.9(4) ?
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
    C1 H1A F6 2_545 0.99 2.53 3.347(4) 140.1
    C1 H1B F3 4_566 0.99 2.46 3.410(5) 161.8
    C2 H2A F4 2_545 0.99 2.48 3.407(4) 154.9
    C3 H3A F1 4_565 0.99 2.51 3.500(4) 176.8
    C4 H4A F6 2_645 0.99 2.36 3.175(4) 139.4
    C6 H6B F4 . 0.99 2.30 3.238(4) 157.6
    C1 H1A Cl1 . 0.99 2.82 3.393(4) 117.7
    C4 H4B Cl2 . 0.99 2.63 3.137(3) 112.2
    C5 H5A Cl2 . 0.99 2.74 3.324(3) 117.9
    C6 H6A Cl2 4_666 0.99 2.77 3.447(3) 126.2
    C8 H8B Cl1 . 0.99 2.73 3.203(4) 109.7
    C12 H12B Cl2 . 0.98 2.78 3.329(4) 116.0
_shelxl_version_number         .2013
data_II
_database_code_depnum_ccdc_archive 'CCDC 1020730'
_audit_creation_method     SHELXL-2013
_chemical_name_systematic
;\
Dichlorido(4,11-dimethyl-1,4,8,11-tetraazabicyclo[6.6.2]hexadecane)\
chromium(III) hexafluorophosphate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H30 Cl2 Cr N4 +, F6 P -'
_chemical_formula_sum     'C14 H30 Cl2 Cr F6 N4 P'
_chemical_formula_iupac     '[Cr Cl2 (C14 H30 N4)] P F6'
_chemical_formula_weight     522.29
_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     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     13.6801(19)
_cell_length_b     12.437(2)
_cell_length_c     12.3864(17)
_cell_angle_alpha     90
_cell_angle_beta     102.028(11)
_cell_angle_gamma     90
_cell_volume     2061.1(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9091
_cell_measurement_theta_min     2.60
_cell_measurement_theta_max     27.94
_cell_measurement_temperature     150(2)
_exptl_crystal_description     block
_exptl_crystal_colour     purple
_exptl_crystal_size_max     0.150
_exptl_crystal_size_mid     0.150
_exptl_crystal_size_min     0.060
_exptl_crystal_density_diffrn     1.683
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1076
_exptl_absorpt_coefficient_mu     0.953
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details
;
[a face-indexed absorption correction was applied;
X-AREA (Stoe & Cie, 2002)]
;
_shelx_estimated_absorpt_T_min     0.870
_shelx_estimated_absorpt_T_max     0.945
_exptl_absorpt_correction_T_min     0.7776
_exptl_absorpt_correction_T_max     0.9006
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Stoe IPDS2'
_diffrn_measurement_method     'ω-scans'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     13450
_diffrn_reflns_av_R_equivalents     0.0905
_diffrn_reflns_theta_min     2.600
_diffrn_reflns_theta_max     26.249
_diffrn_reflns_theta_full     25.000
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
;
_reflns_number_total     4158
_reflns_number_gt     2073
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1019
_refine_ls_R_factor_gt     0.0452
_refine_ls_wR_factor_gt     0.0954
_refine_ls_wR_factor_ref     0.1094
_refine_ls_goodness_of_fit_ref     0.784
_refine_ls_restrained_S_all     0.784
_refine_ls_number_reflns     4158
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0520P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.332
_refine_diff_density_min     -0.786
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cr' 'Cr' 0.3209 0.6236
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         '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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction     'X-AREA (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS86 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL2013 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    Cr Cr1 0.32108(5) 0.56984(5) 0.21705(5) 0.03357(19) Uani d 1 . .
    Cl Cl1 0.46100(9) 0.62992(9) 0.33888(8) 0.0431(3) Uani d 1 . .
    Cl Cl2 0.36519(9) 0.66096(9) 0.07251(8) 0.0423(3) Uani d 1 . .
    N N1 0.2651(3) 0.4975(3) 0.3442(3) 0.0367(8) Uani d 1 . .
    N N2 0.2251(3) 0.7026(3) 0.2372(2) 0.0368(9) Uani d 1 . .
    N N3 0.1984(3) 0.4956(3) 0.1138(2) 0.0331(8) Uani d 1 . .
    N N4 0.3972(3) 0.4231(3) 0.1961(3) 0.0384(9) Uani d 1 . .
    C C1 0.2305(4) 0.5917(3) 0.4026(3) 0.0406(11) Uani d 1 . .
    H H1A 0.2892 0.6311 0.4444 0.049 Uiso calc 1 . .
    H H1B 0.1910 0.5656 0.4558 0.049 Uiso calc 1 . .
    C C2 0.1674(4) 0.6666(4) 0.3209(3) 0.0401(11) Uani d 1 . .
    H H2A 0.1057 0.6291 0.2834 0.048 Uiso calc 1 . .
    H H2B 0.1478 0.7298 0.3600 0.048 Uiso calc 1 . .
    C C3 0.1559(3) 0.7420(4) 0.1358(3) 0.0396(10) Uani d 1 . .
    H H3A 0.1966 0.7733 0.0863 0.048 Uiso calc 1 . .
    H H3B 0.1151 0.8008 0.1573 0.048 Uiso calc 1 . .
    C C4 0.0858(3) 0.6599(4) 0.0706(3) 0.0421(11) Uani d 1 . .
    H H4A 0.0419 0.6316 0.1183 0.051 Uiso calc 1 . .
    H H4B 0.0425 0.6968 0.0074 0.051 Uiso calc 1 . .
    C C5 0.1360(3) 0.5661(4) 0.0269(3) 0.0388(10) Uani d 1 . .
    H H5A 0.0838 0.5211 -0.0193 0.047 Uiso calc 1 . .
    H H5B 0.1793 0.5943 -0.0214 0.047 Uiso calc 1 . .
    C C6 0.2446(4) 0.4113(4) 0.0536(3) 0.0426(11) Uani d 1 . .
    H H6A 0.2768 0.4460 -0.0020 0.051 Uiso calc 1 . .
    H H6B 0.1920 0.3623 0.0144 0.051 Uiso calc 1 . .
    C C7 0.3218(4) 0.3474(4) 0.1338(3) 0.0416(11) Uani d 1 . .
    H H7A 0.2891 0.3073 0.1856 0.050 Uiso calc 1 . .
    H H7B 0.3549 0.2949 0.0931 0.050 Uiso calc 1 . .
    C C8 0.4513(3) 0.3706(4) 0.3011(3) 0.0408(11) Uani d 1 . .
    H H8A 0.5060 0.4190 0.3371 0.049 Uiso calc 1 . .
    H H8B 0.4825 0.3035 0.2816 0.049 Uiso calc 1 . .
    C C9 0.3879(4) 0.3433(4) 0.3847(3) 0.0421(11) Uani d 1 . .
    H H9A 0.3353 0.2922 0.3496 0.051 Uiso calc 1 . .
    H H9B 0.4309 0.3055 0.4474 0.051 Uiso calc 1 . .
    C C10 0.3379(3) 0.4366(4) 0.4302(3) 0.0405(11) Uani d 1 . .
    H H10A 0.3021 0.4089 0.4862 0.049 Uiso calc 1 . .
    H H10B 0.3901 0.4869 0.4679 0.049 Uiso calc 1 . .
    C C11 0.1794(3) 0.4237(4) 0.3005(3) 0.0395(10) Uani d 1 . .
    H H11A 0.1286 0.4316 0.3463 0.047 Uiso calc 1 . .
    H H11B 0.2038 0.3485 0.3080 0.047 Uiso calc 1 . .
    C C12 0.1300(3) 0.4441(4) 0.1802(3) 0.0402(11) Uani d 1 . .
    H H12A 0.1056 0.3749 0.1454 0.048 Uiso calc 1 . .
    H H12B 0.0713 0.4913 0.1777 0.048 Uiso calc 1 . .
    C C13 0.2856(4) 0.7989(4) 0.2819(3) 0.0443(11) Uani d 1 . .
    H H13A 0.3262 0.7820 0.3548 0.053 Uiso calc 1 . .
    H H13B 0.2407 0.8589 0.2883 0.053 Uiso calc 1 . .
    H H13C 0.3294 0.8189 0.2318 0.053 Uiso calc 1 . .
    C C14 0.4760(4) 0.4407(4) 0.1303(4) 0.0469(12) Uani d 1 . .
    H H14A 0.5234 0.4952 0.1666 0.056 Uiso calc 1 . .
    H H14B 0.4447 0.4653 0.0560 0.056 Uiso calc 1 . .
    H H14C 0.5116 0.3731 0.1252 0.056 Uiso calc 1 . .
    P P1 0.12310(10) 0.10057(10) 0.18374(9) 0.0430(3) Uani d 1 . .
    F F1 0.0182(2) 0.0745(3) 0.1049(2) 0.0696(9) Uani d 1 . .
    F F2 0.0958(3) 0.0212(2) 0.2740(2) 0.0688(9) Uani d 1 . .
    F F3 0.2260(2) 0.1297(3) 0.2639(2) 0.0718(9) Uani d 1 . .
    F F4 0.1495(2) 0.1810(2) 0.0940(2) 0.0637(8) Uani d 1 . .
    F F5 0.1746(2) 0.0057(2) 0.1317(2) 0.0615(8) Uani d 1 . .
    F F6 0.0718(2) 0.1974(2) 0.2371(2) 0.0664(9) Uani d 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Cr1 N1 . 2.093(3) ?
    Cr1 N3 . 2.100(3) ?
    Cr1 N4 . 2.143(4) ?
    Cr1 N2 . 2.155(4) ?
    Cr1 Cl1 . 2.3012(13) ?
    Cr1 Cl2 . 2.3031(12) ?
    N1 C11 . 1.499(5) ?
    N1 C10 . 1.502(5) ?
    N1 C1 . 1.504(5) ?
    N2 C3 . 1.490(5) ?
    N2 C13 . 1.495(5) ?
    N2 C2 . 1.497(5) ?
    N3 C6 . 1.500(5) ?
    N3 C5 . 1.507(5) ?
    N3 C12 . 1.511(5) ?
    N4 C7 . 1.487(6) ?
    N4 C14 . 1.498(5) ?
    N4 C8 . 1.505(5) ?
    C1 C2 . 1.508(6) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.514(6) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.510(6) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 C7 . 1.516(6) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C9 . 1.520(6) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.516(6) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C12 . 1.524(5) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    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 ?
    P1 F5 . 1.579(3) ?
    P1 F3 . 1.587(3) ?
    P1 F1 . 1.592(3) ?
    P1 F4 . 1.592(3) ?
    P1 F2 . 1.593(3) ?
    P1 F6 . 1.605(3) ?
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
    N1 Cr1 N3 . . 84.18(13) ?
    N1 Cr1 N4 . . 89.33(13) ?
    N3 Cr1 N4 . . 84.16(14) ?
    N1 Cr1 N2 . . 85.11(13) ?
    N3 Cr1 N2 . . 88.80(14) ?
    N4 Cr1 N2 . . 171.44(14) ?
    N1 Cr1 Cl1 . . 91.75(10) ?
    N3 Cr1 Cl1 . . 172.78(10) ?
    N4 Cr1 Cl1 . . 89.84(10) ?
    N2 Cr1 Cl1 . . 96.82(10) ?
    N1 Cr1 Cl2 . . 173.17(11) ?
    N3 Cr1 Cl2 . . 92.77(9) ?
    N4 Cr1 Cl2 . . 96.45(9) ?
    N2 Cr1 Cl2 . . 88.73(9) ?
    Cl1 Cr1 Cl2 . . 91.90(5) ?
    C11 N1 C10 . . 107.4(3) ?
    C11 N1 C1 . . 110.5(3) ?
    C10 N1 C1 . . 106.3(3) ?
    C11 N1 Cr1 . . 111.9(2) ?
    C10 N1 Cr1 . . 117.3(3) ?
    C1 N1 Cr1 . . 103.2(2) ?
    C3 N2 C13 . . 104.7(3) ?
    C3 N2 C2 . . 110.4(3) ?
    C13 N2 C2 . . 108.3(3) ?
    C3 N2 Cr1 . . 116.7(2) ?
    C13 N2 Cr1 . . 110.7(3) ?
    C2 N2 Cr1 . . 105.9(2) ?
    C6 N3 C5 . . 106.6(3) ?
    C6 N3 C12 . . 110.3(3) ?
    C5 N3 C12 . . 108.2(3) ?
    C6 N3 Cr1 . . 104.1(3) ?
    C5 N3 Cr1 . . 116.2(3) ?
    C12 N3 Cr1 . . 111.2(2) ?
    C7 N4 C14 . . 108.1(3) ?
    C7 N4 C8 . . 109.7(3) ?
    C14 N4 C8 . . 104.7(3) ?
    C7 N4 Cr1 . . 107.5(3) ?
    C14 N4 Cr1 . . 111.4(3) ?
    C8 N4 Cr1 . . 115.4(2) ?
    N1 C1 C2 . . 110.6(3) ?
    N1 C1 H1A . . 109.5 ?
    C2 C1 H1A . . 109.5 ?
    N1 C1 H1B . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 108.1 ?
    N2 C2 C1 . . 109.8(4) ?
    N2 C2 H2A . . 109.7 ?
    C1 C2 H2A . . 109.7 ?
    N2 C2 H2B . . 109.7 ?
    C1 C2 H2B . . 109.7 ?
    H2A C2 H2B . . 108.2 ?
    N2 C3 C4 . . 116.7(4) ?
    N2 C3 H3A . . 108.1 ?
    C4 C3 H3A . . 108.1 ?
    N2 C3 H3B . . 108.1 ?
    C4 C3 H3B . . 108.1 ?
    H3A C3 H3B . . 107.3 ?
    C5 C4 C3 . . 115.3(4) ?
    C5 C4 H4A . . 108.5 ?
    C3 C4 H4A . . 108.5 ?
    C5 C4 H4B . . 108.5 ?
    C3 C4 H4B . . 108.5 ?
    H4A C4 H4B . . 107.5 ?
    N3 C5 C4 . . 115.2(3) ?
    N3 C5 H5A . . 108.5 ?
    C4 C5 H5A . . 108.5 ?
    N3 C5 H5B . . 108.5 ?
    C4 C5 H5B . . 108.5 ?
    H5A C5 H5B . . 107.5 ?
    N3 C6 C7 . . 110.4(3) ?
    N3 C6 H6A . . 109.6 ?
    C7 C6 H6A . . 109.6 ?
    N3 C6 H6B . . 109.6 ?
    C7 C6 H6B . . 109.6 ?
    H6A C6 H6B . . 108.1 ?
    N4 C7 C6 . . 108.7(4) ?
    N4 C7 H7A . . 109.9 ?
    C6 C7 H7A . . 109.9 ?
    N4 C7 H7B . . 109.9 ?
    C6 C7 H7B . . 109.9 ?
    H7A C7 H7B . . 108.3 ?
    N4 C8 C9 . . 115.9(4) ?
    N4 C8 H8A . . 108.3 ?
    C9 C8 H8A . . 108.3 ?
    N4 C8 H8B . . 108.3 ?
    C9 C8 H8B . . 108.3 ?
    H8A C8 H8B . . 107.4 ?
    C10 C9 C8 . . 116.6(4) ?
    C10 C9 H9A . . 108.1 ?
    C8 C9 H9A . . 108.1 ?
    C10 C9 H9B . . 108.1 ?
    C8 C9 H9B . . 108.1 ?
    H9A C9 H9B . . 107.3 ?
    N1 C10 C9 . . 114.0(3) ?
    N1 C10 H10A . . 108.8 ?
    C9 C10 H10A . . 108.8 ?
    N1 C10 H10B . . 108.8 ?
    C9 C10 H10B . . 108.8 ?
    H10A C10 H10B . . 107.7 ?
    N1 C11 C12 . . 113.9(3) ?
    N1 C11 H11A . . 108.8 ?
    C12 C11 H11A . . 108.8 ?
    N1 C11 H11B . . 108.8 ?
    C12 C11 H11B . . 108.8 ?
    H11A C11 H11B . . 107.7 ?
    N3 C12 C11 . . 113.9(4) ?
    N3 C12 H12A . . 108.8 ?
    C11 C12 H12A . . 108.8 ?
    N3 C12 H12B . . 108.8 ?
    C11 C12 H12B . . 108.8 ?
    H12A C12 H12B . . 107.7 ?
    N2 C13 H13A . . 109.5 ?
    N2 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    N2 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    N4 C14 H14A . . 109.5 ?
    N4 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    N4 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    F5 P1 F3 . . 90.73(18) ?
    F5 P1 F1 . . 91.12(17) ?
    F3 P1 F1 . . 178.15(19) ?
    F5 P1 F4 . . 89.96(15) ?
    F3 P1 F4 . . 89.57(17) ?
    F1 P1 F4 . . 90.36(17) ?
    F5 P1 F2 . . 90.75(16) ?
    F3 P1 F2 . . 90.55(17) ?
    F1 P1 F2 . . 89.50(18) ?
    F4 P1 F2 . . 179.28(19) ?
    F5 P1 F6 . . 179.47(19) ?
    F3 P1 F6 . . 88.75(17) ?
    F1 P1 F6 . . 89.40(17) ?
    F4 P1 F6 . . 89.91(17) ?
    F2 P1 F6 . . 89.38(16) ?
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
    C11 N1 C1 C2 . . . . -71.2(4) ?
    C10 N1 C1 C2 . . . . 172.6(4) ?
    Cr1 N1 C1 C2 . . . . 48.6(4) ?
    C3 N2 C2 C1 . . . . 159.5(3) ?
    C13 N2 C2 C1 . . . . -86.4(4) ?
    Cr1 N2 C2 C1 . . . . 32.3(4) ?
    N1 C1 C2 N2 . . . . -56.7(5) ?
    C13 N2 C3 C4 . . . . 178.8(4) ?
    C2 N2 C3 C4 . . . . -64.9(5) ?
    Cr1 N2 C3 C4 . . . . 56.0(5) ?
    N2 C3 C4 C5 . . . . -60.3(5) ?
    C6 N3 C5 C4 . . . . -177.6(4) ?
    C12 N3 C5 C4 . . . . 63.7(5) ?
    Cr1 N3 C5 C4 . . . . -62.1(4) ?
    C3 C4 C5 N3 . . . . 62.9(5) ?
    C5 N3 C6 C7 . . . . 170.9(4) ?
    C12 N3 C6 C7 . . . . -71.8(4) ?
    Cr1 N3 C6 C7 . . . . 47.6(4) ?
    C14 N4 C7 C6 . . . . -86.8(4) ?
    C8 N4 C7 C6 . . . . 159.7(3) ?
    Cr1 N4 C7 C6 . . . . 33.5(4) ?
    N3 C6 C7 N4 . . . . -56.2(5) ?
    C7 N4 C8 C9 . . . . -64.3(5) ?
    C14 N4 C8 C9 . . . . -180.0(4) ?
    Cr1 N4 C8 C9 . . . . 57.2(4) ?
    N4 C8 C9 C10 . . . . -61.3(5) ?
    C11 N1 C10 C9 . . . . 66.6(5) ?
    C1 N1 C10 C9 . . . . -175.1(4) ?
    Cr1 N1 C10 C9 . . . . -60.3(4) ?
    C8 C9 C10 N1 . . . . 61.5(5) ?
    C10 N1 C11 C12 . . . . -149.2(4) ?
    C1 N1 C11 C12 . . . . 95.2(4) ?
    Cr1 N1 C11 C12 . . . . -19.2(5) ?
    C6 N3 C12 C11 . . . . 95.5(4) ?
    C5 N3 C12 C11 . . . . -148.2(4) ?
    Cr1 N3 C12 C11 . . . . -19.6(4) ?
    N1 C11 C12 N3 . . . . 25.8(5) ?
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
    C1 H1B F5 4_566 0.99 2.41 3.318(5) 153.0
    C2 H2A F1 2 0.99 2.50 3.094(5) 118.6
    C2 H2A F6 2 0.99 2.53 3.223(6) 126.5
    C7 H7A F4 . 0.99 2.55 3.098(6) 114.8
    C12 H12B F2 2 0.99 2.51 3.393(6) 148.6
    C3 H3A Cl2 . 0.99 2.73 3.280(5) 115.3
    C5 H5B Cl2 . 0.99 2.70 3.287(5) 118.5
    C8 H8A Cl1 . 0.99 2.70 3.258(5) 116.3
    C8 H8B Cl1 2_645 0.99 2.82 3.778(4) 162.4
    C10 H10B Cl1 . 0.99 2.70 3.270(5) 116.7
    C13 H13A Cl1 . 0.98 2.68 3.157(5) 110.5
    C13 H13A Cl2 4_576 0.98 2.73 3.572(4) 144.2
    C14 H14B Cl2 . 0.98 2.69 3.141(5) 108.4
_shelxl_version_number         .2013
