# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_Mn(nPrdhbpy)Cl
_database_code_depnum_ccdc_archive 'CCDC 2255849'
loop_
_audit_author_name
_audit_author_address
'Diane A. Dickie'
;University of Virginia
United States of America
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C64 H66 Cl2 Mn2 N6 O8'
_chemical_formula_iupac          ?
_chemical_formula_weight         1228.00

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   15.3780(4)
_cell_length_b                   9.8097(2)
_cell_length_c                   20.2954(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.0756(18)
_cell_angle_gamma                90
_cell_volume                     2893.51(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6227
_cell_measurement_theta_min      3.0406
_cell_measurement_theta_max      68.2967
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            brown-yellow
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280

_exptl_absorpt_coefficient_mu    4.904
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.87

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             0.06
_diffrn_source_current           1.1
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'HELIOS MX double bounce multilayer mirror'

_diffrn_measurement_device       'Kappa four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon III'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            34823
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             5293
_reflns_number_gt                4138
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1376
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_number_reflns         5293
_refine_ls_number_parameters     404
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.9732P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.357
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn Mn1 0.43635(3) 0.13608(5) 0.01179(2) 0.02189(15) Uani d . . . 1.0 . .
Cl Cl1 0.38065(6) 0.26500(7) 0.09194(4) 0.0308(2) Uani d . . . 1.0 . .
O O1 0.50104(14) -0.0105(2) 0.06840(10) 0.0236(4) Uani d . . . 1.0 . .
O O2 0.49512(18) -0.1709(2) 0.16980(11) 0.0333(5) Uani d . . . 1.0 . .
O O3 0.32833(15) 0.0376(2) -0.02820(11) 0.0278(5) Uani d . . . 1.0 . .
O O4 0.18297(18) -0.0922(3) -0.02256(16) 0.0459(7) Uani d . . . 1.0 . .
N N1 0.55615(17) 0.2400(2) 0.03549(12) 0.0221(5) Uani d . . . 1.0 . .
N N2 0.39842(18) 0.2779(3) -0.06479(12) 0.0248(5) Uani d . . . 1.0 . .
C C1 0.5623(2) 0.0142(3) 0.13159(15) 0.0241(6) Uani d . . . 1.0 . .
C C2 0.5626(2) -0.0733(3) 0.18719(16) 0.0289(7) Uani d . . . 1.0 . .
C C3 0.6271(3) -0.0601(3) 0.25235(16) 0.0312(7) Uani d . . . 1.0 . .
H H3 0.625837 -0.120382 0.288671 0.037 Uiso calc U . R 1.0 . .
C C4 0.6945(2) 0.0415(3) 0.26551(16) 0.0304(7) Uani d . . . 1.0 . .
C C5 0.6941(2) 0.1290(3) 0.21253(16) 0.0290(7) Uani d . . . 1.0 . .
H H5 0.738958 0.199268 0.221514 0.035 Uiso calc U . R 1.0 . .
C C6 0.6287(2) 0.1174(3) 0.14495(15) 0.0254(6) Uani d . . . 1.0 . .
C C7 0.6327(2) 0.2134(3) 0.09021(15) 0.0251(6) Uani d . . . 1.0 . .
C C8 0.7148(2) 0.2804(3) 0.09421(16) 0.0302(7) Uani d . . . 1.0 . .
H H8 0.76985 0.259146 0.130851 0.036 Uiso calc U . R 1.0 . .
C C9 0.7159(2) 0.3766(3) 0.04545(18) 0.0330(7) Uani d . . . 1.0 . .
H H9 0.771511 0.422681 0.048803 0.04 Uiso calc U . R 1.0 . .
C C10 0.6366(2) 0.4066(3) -0.00837(16) 0.0292(7) Uani d . . . 1.0 . .
H H10 0.636397 0.474478 -0.041794 0.035 Uiso calc U . R 1.0 . .
C C11 0.5570(2) 0.3356(3) -0.01268(15) 0.0241(6) Uani d . . . 1.0 . .
C C12 0.4686(2) 0.3584(3) -0.06773(15) 0.0263(7) Uani d . . . 1.0 . .
C C13 0.4557(3) 0.4579(3) -0.11815(16) 0.0317(7) Uani d . . . 1.0 . .
H H13 0.503575 0.519815 -0.117171 0.038 Uiso calc U . R 1.0 . .
C C14 0.3712(3) 0.4650(4) -0.17007(17) 0.0384(8) Uani d . . . 1.0 . .
H H14 0.361498 0.528954 -0.206946 0.046 Uiso calc U . R 1.0 . .
C C15 0.3013(3) 0.3798(4) -0.16833(17) 0.0380(8) Uani d . . . 1.0 . .
H H15 0.244136 0.382317 -0.205139 0.046 Uiso calc U . R 1.0 . .
C C16 0.3135(2) 0.2889(3) -0.11265(16) 0.0308(7) Uani d . . . 1.0 . .
C C17 0.2358(2) 0.2107(4) -0.10497(17) 0.0333(7) Uani d . . . 1.0 . .
C C18 0.2471(2) 0.0923(4) -0.06418(17) 0.0322(7) Uani d . . . 1.0 . .
C C19 0.1667(3) 0.0231(4) -0.0626(2) 0.0397(9) Uani d . . . 1.0 . .
C C20 0.0796(3) 0.0712(5) -0.0999(2) 0.0513(11) Uani d . . . 1.0 . .
H H20 0.026766 0.021651 -0.099356 0.062 Uiso calc U . R 1.0 . .
C C21 0.0691(3) 0.1919(5) -0.1382(2) 0.0535(11) Uani d . . . 1.0 . .
C C22 0.1461(3) 0.2579(4) -0.1402(2) 0.0451(10) Uani d . . . 1.0 . .
H H22 0.138996 0.339652 -0.166534 0.054 Uiso calc U . R 1.0 . .
C C23 0.7640(3) 0.0522(4) 0.33788(17) 0.0380(8) Uani d . . . 1.0 . .
H H23A 0.730961 0.065333 0.371896 0.046 Uiso calc U . R 1.0 . .
H H23B 0.803098 0.13336 0.340114 0.046 Uiso calc U . R 1.0 . .
C C24 0.8254(3) -0.0739(5) 0.3585(2) 0.0541(11) Uani d . . . 1.0 . .
H H24A 0.786127 -0.155569 0.354302 0.065 Uiso calc U . R 1.0 . .
H H24B 0.860422 -0.084759 0.325653 0.065 Uiso calc U . R 1.0 . .
C C25 0.8927(4) -0.0655(6) 0.4326(2) 0.0769(17) Uani d . . . 1.0 . .
H H25A 0.928546 -0.149891 0.443837 0.115 Uiso calc U . R 1.0 . .
H H25B 0.858425 -0.053045 0.465268 0.115 Uiso calc U . R 1.0 . .
H H25C 0.934252 0.011967 0.436277 0.115 Uiso calc U . R 1.0 . .
C C31 0.1046(3) -0.1640(5) -0.0183(3) 0.0635(13) Uani d . . . 1.0 . .
H H31A 0.066741 -0.193195 -0.065102 0.095 Uiso calc U . R 1.0 . .
H H31B 0.068418 -0.104176 0.001381 0.095 Uiso calc U . R 1.0 . .
H H31C 0.124694 -0.244188 0.011602 0.095 Uiso calc U . R 1.0 . .
C C32 0.4878(3) -0.2541(4) 0.2253(2) 0.0439(9) Uani d . . . 1.0 . .
H H32A 0.437941 -0.320228 0.206906 0.066 Uiso calc U . R 1.0 . .
H H32B 0.474483 -0.196688 0.260309 0.066 Uiso calc U . R 1.0 . .
H H32C 0.545885 -0.302661 0.246693 0.066 Uiso calc U . R 1.0 . .
C C26 -0.0220(7) 0.2671(12) -0.1840(6) 0.043(2) Uani d . P . 0.539(11) A 1
H H26A -0.07502 0.227055 -0.173361 0.051 Uiso calc U P R 0.539(11) A 1
H H26B -0.017932 0.364339 -0.170309 0.051 Uiso calc U P R 0.539(11) A 1
C C27 -0.0406(5) 0.2585(9) -0.2624(4) 0.048(3) Uani d . P . 0.539(11) A 1
H H27A 0.010935 0.301951 -0.273701 0.058 Uiso calc U P R 0.539(11) A 1
H H27B -0.097331 0.310128 -0.286784 0.058 Uiso calc U P R 0.539(11) A 1
C C28 -0.0519(11) 0.1087(11) -0.2899(8) 0.053(3) Uani d . P . 0.539(11) A 1
H H28A -0.063962 0.108804 -0.340417 0.08 Uiso calc U P R 0.539(11) A 1
H H28B -0.103428 0.065531 -0.279611 0.08 Uiso calc U P R 0.539(11) A 1
H H28C 0.004768 0.057663 -0.266968 0.08 Uiso calc U P R 0.539(11) A 1
C C26A -0.0317(9) 0.2125(14) -0.1705(7) 0.043(3) Uani d . P . 0.461(11) A 2
H H26C -0.043377 0.310583 -0.18135 0.052 Uiso calc U P R 0.461(11) A 2
H H26D -0.061867 0.18809 -0.135837 0.052 Uiso calc U P R 0.461(11) A 2
C C27A -0.0770(6) 0.1306(10) -0.2371(5) 0.050(3) Uani d . P . 0.461(11) A 2
H H27C -0.066927 0.032109 -0.226657 0.06 Uiso calc U P R 0.461(11) A 2
H H27D -0.14416 0.147426 -0.253282 0.06 Uiso calc U P R 0.461(11) A 2
C C28A -0.0398(10) 0.1671(16) -0.2933(8) 0.056(4) Uani d . P . 0.461(11) A 2
H H28D -0.07243 0.115734 -0.335554 0.084 Uiso calc U P R 0.461(11) A 2
H H28E 0.025938 0.144823 -0.27867 0.084 Uiso calc U P R 0.461(11) A 2
H H28F -0.048065 0.265003 -0.302916 0.084 Uiso calc U P R 0.461(11) A 2
N N3 0.1520(4) 0.0556(6) 0.1423(4) 0.114(2) Uani d . . . 1.0 . .
C C29 0.3020(3) -0.0463(4) 0.1348(2) 0.0523(11) Uani d . . . 1.0 . .
H H29A 0.295756 -0.063047 0.085868 0.078 Uiso calc U . R 1.0 . .
H H29B 0.31382 -0.132739 0.160453 0.078 Uiso calc U . R 1.0 . .
H H29C 0.353346 0.016356 0.155301 0.078 Uiso calc U . R 1.0 . .
C C30 0.2184(4) 0.0129(5) 0.1389(3) 0.0660(14) Uani d . . . 1.0 . .


_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
Mn1 O3 . 1.863(2) ?
Mn1 O1 . 1.906(2) ?
Mn1 N1 . 2.021(3) ?
Mn1 N2 . 2.024(3) ?
Mn1 Cl1 . 2.4269(8) ?
Mn1 O1 3_655 2.473(2) ?
O1 C1 . 1.342(4) ?
O2 C2 . 1.371(4) ?
O2 C32 . 1.425(4) ?
O3 C18 . 1.336(4) ?
O4 C19 . 1.367(5) ?
O4 C31 . 1.422(5) ?
N1 C7 . 1.354(4) ?
N1 C11 . 1.358(4) ?
N2 C16 . 1.353(4) ?
N2 C12 . 1.355(4) ?
C1 C6 . 1.401(4) ?
C1 C2 . 1.416(4) ?
C2 C3 . 1.375(5) ?
C3 C4 . 1.400(5) ?
C3 H3 . 0.95 ?
C4 C5 . 1.374(5) ?
C4 C23 . 1.511(5) ?
C5 C6 . 1.415(4) ?
C5 H5 . 0.95 ?
C6 C7 . 1.473(4) ?
C7 C8 . 1.402(5) ?
C8 C9 . 1.372(5) ?
C8 H8 . 0.95 ?
C9 C10 . 1.377(5) ?
C9 H9 . 0.95 ?
C10 C11 . 1.386(5) ?
C10 H10 . 0.95 ?
C11 C12 . 1.468(5) ?
C12 C13 . 1.380(4) ?
C13 C14 . 1.381(5) ?
C13 H13 . 0.95 ?
C14 C15 . 1.371(6) ?
C14 H14 . 0.95 ?
C15 C16 . 1.403(5) ?
C15 H15 . 0.95 ?
C16 C17 . 1.470(5) ?
C17 C18 . 1.404(5) ?
C17 C22 . 1.408(5) ?
C18 C19 . 1.421(5) ?
C19 C20 . 1.388(6) ?
C20 C21 . 1.397(7) ?
C20 H20 . 0.95 ?
C21 C22 . 1.362(6) ?
C21 C26A . 1.487(13) ?
C21 C26 . 1.588(11) ?
C22 H22 . 0.95 ?
C23 C24 . 1.529(5) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C25 . 1.524(6) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
C31 H31A . 0.98 ?
C31 H31B . 0.98 ?
C31 H31C . 0.98 ?
C32 H32A . 0.98 ?
C32 H32B . 0.98 ?
C32 H32C . 0.98 ?
C26 C27 . 1.524(16) ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C27 C28 . 1.561(13) ?
C27 H27A . 0.99 ?
C27 H27B . 0.99 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C26A C27A . 1.531(17) ?
C26A H26C . 0.99 ?
C26A H26D . 0.99 ?
C27A C28A . 1.48(2) ?
C27A H27C . 0.99 ?
C27A H27D . 0.99 ?
C28A H28D . 0.98 ?
C28A H28E . 0.98 ?
C28A H28F . 0.98 ?
N3 C30 . 1.125(7) ?
C29 C30 . 1.438(7) ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?

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
O3 Mn1 O1 . . 94.98(9) ?
O3 Mn1 N1 . . 168.20(9) ?
O1 Mn1 N1 . . 88.94(9) ?
O3 Mn1 N2 . . 91.70(10) ?
O1 Mn1 N2 . . 160.76(10) ?
N1 Mn1 N2 . . 81.23(10) ?
O3 Mn1 Cl1 . . 95.88(7) ?
O1 Mn1 Cl1 . . 102.61(7) ?
N1 Mn1 Cl1 . . 94.10(7) ?
N2 Mn1 Cl1 . . 94.61(7) ?
O3 Mn1 O1 . 3_655 86.47(8) ?
O1 Mn1 O1 . 3_655 77.41(8) ?
N1 Mn1 O1 . 3_655 83.53(8) ?
N2 Mn1 O1 . 3_655 85.03(8) ?
Cl1 Mn1 O1 . 3_655 177.63(6) ?
C1 O1 Mn1 . . 120.33(18) ?
C1 O1 Mn1 . 3_655 114.61(18) ?
Mn1 O1 Mn1 . 3_655 102.59(8) ?
C2 O2 C32 . . 116.5(3) ?
C18 O3 Mn1 . . 124.8(2) ?
C19 O4 C31 . . 116.8(4) ?
C7 N1 C11 . . 120.9(3) ?
C7 N1 Mn1 . . 125.3(2) ?
C11 N1 Mn1 . . 113.5(2) ?
C16 N2 C12 . . 121.2(3) ?
C16 N2 Mn1 . . 125.0(2) ?
C12 N2 Mn1 . . 113.6(2) ?
O1 C1 C6 . . 123.7(3) ?
O1 C1 C2 . . 118.1(3) ?
C6 C1 C2 . . 118.1(3) ?
O2 C2 C3 . . 124.1(3) ?
O2 C2 C1 . . 114.4(3) ?
C3 C2 C1 . . 121.6(3) ?
C2 C3 C4 . . 120.4(3) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C5 C4 C3 . . 118.8(3) ?
C5 C4 C23 . . 122.6(3) ?
C3 C4 C23 . . 118.6(3) ?
C4 C5 C6 . . 121.9(3) ?
C4 C5 H5 . . 119.0 ?
C6 C5 H5 . . 119.0 ?
C1 C6 C5 . . 119.2(3) ?
C1 C6 C7 . . 121.6(3) ?
C5 C6 C7 . . 119.2(3) ?
N1 C7 C8 . . 118.8(3) ?
N1 C7 C6 . . 120.2(3) ?
C8 C7 C6 . . 121.0(3) ?
C9 C8 C7 . . 120.3(3) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C8 C9 C10 . . 120.2(3) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C9 C10 C11 . . 118.5(3) ?
C9 C10 H10 . . 120.7 ?
C11 C10 H10 . . 120.7 ?
N1 C11 C10 . . 121.2(3) ?
N1 C11 C12 . . 115.4(3) ?
C10 C11 C12 . . 123.4(3) ?
N2 C12 C13 . . 121.4(3) ?
N2 C12 C11 . . 115.5(3) ?
C13 C12 C11 . . 123.1(3) ?
C12 C13 C14 . . 118.2(3) ?
C12 C13 H13 . . 120.9 ?
C14 C13 H13 . . 120.9 ?
C15 C14 C13 . . 119.9(3) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 120.6(3) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
N2 C16 C15 . . 118.2(3) ?
N2 C16 C17 . . 120.6(3) ?
C15 C16 C17 . . 121.2(3) ?
C18 C17 C22 . . 118.9(4) ?
C18 C17 C16 . . 123.1(3) ?
C22 C17 C16 . . 118.0(3) ?
O3 C18 C17 . . 124.6(3) ?
O3 C18 C19 . . 117.5(3) ?
C17 C18 C19 . . 117.9(3) ?
O4 C19 C20 . . 124.2(4) ?
O4 C19 C18 . . 114.6(3) ?
C20 C19 C18 . . 121.1(4) ?
C19 C20 C21 . . 120.5(4) ?
C19 C20 H20 . . 119.8 ?
C21 C20 H20 . . 119.8 ?
C22 C21 C20 . . 118.5(4) ?
C22 C21 C26A . . 135.6(7) ?
C20 C21 C26A . . 105.9(7) ?
C22 C21 C26 . . 111.8(6) ?
C20 C21 C26 . . 129.7(6) ?
C21 C22 C17 . . 123.1(4) ?
C21 C22 H22 . . 118.5 ?
C17 C22 H22 . . 118.5 ?
C4 C23 C24 . . 112.8(3) ?
C4 C23 H23A . . 109.0 ?
C24 C23 H23A . . 109.0 ?
C4 C23 H23B . . 109.0 ?
C24 C23 H23B . . 109.0 ?
H23A C23 H23B . . 107.8 ?
C25 C24 C23 . . 112.7(4) ?
C25 C24 H24A . . 109.1 ?
C23 C24 H24A . . 109.1 ?
C25 C24 H24B . . 109.1 ?
C23 C24 H24B . . 109.1 ?
H24A C24 H24B . . 107.8 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
O4 C31 H31A . . 109.5 ?
O4 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
O4 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
O2 C32 H32A . . 109.5 ?
O2 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
O2 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C27 C26 C21 . . 114.4(8) ?
C27 C26 H26A . . 108.7 ?
C21 C26 H26A . . 108.7 ?
C27 C26 H26B . . 108.7 ?
C21 C26 H26B . . 108.7 ?
H26A C26 H26B . . 107.6 ?
C26 C27 C28 . . 112.7(8) ?
C26 C27 H27A . . 109.1 ?
C28 C27 H27A . . 109.1 ?
C26 C27 H27B . . 109.1 ?
C28 C27 H27B . . 109.1 ?
H27A C27 H27B . . 107.8 ?
C27 C28 H28A . . 109.5 ?
C27 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C27 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C21 C26A C27A . . 115.2(9) ?
C21 C26A H26C . . 108.5 ?
C27A C26A H26C . . 108.5 ?
C21 C26A H26D . . 108.5 ?
C27A C26A H26D . . 108.5 ?
H26C C26A H26D . . 107.5 ?
C28A C27A C26A . . 112.0(10) ?
C28A C27A H27C . . 109.2 ?
C26A C27A H27C . . 109.2 ?
C28A C27A H27D . . 109.2 ?
C26A C27A H27D . . 109.2 ?
H27C C27A H27D . . 107.9 ?
C27A C28A H28D . . 109.5 ?
C27A C28A H28E . . 109.5 ?
H28D C28A H28E . . 109.5 ?
C27A C28A H28F . . 109.5 ?
H28D C28A H28F . . 109.5 ?
H28E C28A H28F . . 109.5 ?
C30 C29 H29A . . 109.5 ?
C30 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C30 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
N3 C30 C29 . . 178.0(6) ?

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
O1 Mn1 O3 C18 . . . . 166.1(2) ?
N1 Mn1 O3 C18 . . . . -84.9(5) ?
N2 Mn1 O3 C18 . . . . -32.0(2) ?
Cl1 Mn1 O3 C18 . . . . 62.8(2) ?
O1 Mn1 O3 C18 3_655 . . . -116.9(2) ?
Mn1 O1 C1 C6 . . . . -45.3(4) ?
Mn1 O1 C1 C6 3_655 . . . 77.8(3) ?
Mn1 O1 C1 C2 . . . . 137.9(2) ?
Mn1 O1 C1 C2 3_655 . . . -99.0(3) ?
C32 O2 C2 C3 . . . . 6.0(5) ?
C32 O2 C2 C1 . . . . -175.0(3) ?
O1 C1 C2 O2 . . . . -3.4(4) ?
C6 C1 C2 O2 . . . . 179.7(3) ?
O1 C1 C2 C3 . . . . 175.7(3) ?
C6 C1 C2 C3 . . . . -1.2(5) ?
O2 C2 C3 C4 . . . . 179.2(3) ?
C1 C2 C3 C4 . . . . 0.2(5) ?
C2 C3 C4 C5 . . . . 1.1(5) ?
C2 C3 C4 C23 . . . . -180.0(3) ?
C3 C4 C5 C6 . . . . -1.3(5) ?
C23 C4 C5 C6 . . . . 179.8(3) ?
O1 C1 C6 C5 . . . . -175.8(3) ?
C2 C1 C6 C5 . . . . 1.0(4) ?
O1 C1 C6 C7 . . . . 3.7(5) ?
C2 C1 C6 C7 . . . . -179.5(3) ?
C4 C5 C6 C1 . . . . 0.2(5) ?
C4 C5 C6 C7 . . . . -179.3(3) ?
C11 N1 C7 C8 . . . . -3.8(4) ?
Mn1 N1 C7 C8 . . . . 170.5(2) ?
C11 N1 C7 C6 . . . . 175.2(3) ?
Mn1 N1 C7 C6 . . . . -10.6(4) ?
C1 C6 C7 N1 . . . . 25.1(4) ?
C5 C6 C7 N1 . . . . -155.3(3) ?
C1 C6 C7 C8 . . . . -155.9(3) ?
C5 C6 C7 C8 . . . . 23.6(4) ?
N1 C7 C8 C9 . . . . 3.5(5) ?
C6 C7 C8 C9 . . . . -175.4(3) ?
C7 C8 C9 C10 . . . . -0.9(5) ?
C8 C9 C10 C11 . . . . -1.4(5) ?
C7 N1 C11 C10 . . . . 1.5(4) ?
Mn1 N1 C11 C10 . . . . -173.4(2) ?
C7 N1 C11 C12 . . . . -177.6(3) ?
Mn1 N1 C11 C12 . . . . 7.5(3) ?
C9 C10 C11 N1 . . . . 1.1(5) ?
C9 C10 C11 C12 . . . . -179.8(3) ?
C16 N2 C12 C13 . . . . 2.2(4) ?
Mn1 N2 C12 C13 . . . . 178.0(2) ?
C16 N2 C12 C11 . . . . -179.9(3) ?
Mn1 N2 C12 C11 . . . . -4.1(3) ?
N1 C11 C12 N2 . . . . -2.3(4) ?
C10 C11 C12 N2 . . . . 178.7(3) ?
N1 C11 C12 C13 . . . . 175.6(3) ?
C10 C11 C12 C13 . . . . -3.5(5) ?
N2 C12 C13 C14 . . . . -6.2(5) ?
C11 C12 C13 C14 . . . . 176.0(3) ?
C12 C13 C14 C15 . . . . 3.7(5) ?
C13 C14 C15 C16 . . . . 2.7(5) ?
C12 N2 C16 C15 . . . . 4.2(4) ?
Mn1 N2 C16 C15 . . . . -171.1(2) ?
C12 N2 C16 C17 . . . . -173.9(3) ?
Mn1 N2 C16 C17 . . . . 10.9(4) ?
C14 C15 C16 N2 . . . . -6.6(5) ?
C14 C15 C16 C17 . . . . 171.4(3) ?
N2 C16 C17 C18 . . . . -21.3(5) ?
C15 C16 C17 C18 . . . . 160.6(3) ?
N2 C16 C17 C22 . . . . 158.4(3) ?
C15 C16 C17 C22 . . . . -19.6(5) ?
Mn1 O3 C18 C17 . . . . 31.5(4) ?
Mn1 O3 C18 C19 . . . . -150.5(2) ?
C22 C17 C18 O3 . . . . -179.8(3) ?
C16 C17 C18 O3 . . . . 0.0(5) ?
C22 C17 C18 C19 . . . . 2.2(5) ?
C16 C17 C18 C19 . . . . -178.0(3) ?
C31 O4 C19 C20 . . . . -1.5(5) ?
C31 O4 C19 C18 . . . . 179.0(3) ?
O3 C18 C19 O4 . . . . 1.1(4) ?
C17 C18 C19 O4 . . . . 179.2(3) ?
O3 C18 C19 C20 . . . . -178.4(3) ?
C17 C18 C19 C20 . . . . -0.3(5) ?
O4 C19 C20 C21 . . . . 178.5(3) ?
C18 C19 C20 C21 . . . . -2.1(6) ?
C19 C20 C21 C22 . . . . 2.5(6) ?
C19 C20 C21 C26A . . . . -179.6(6) ?
C19 C20 C21 C26 . . . . -179.6(7) ?
C20 C21 C22 C17 . . . . -0.5(6) ?
C26A C21 C22 C17 . . . . -177.6(8) ?
C26 C21 C22 C17 . . . . -178.8(6) ?
C18 C17 C22 C21 . . . . -1.9(5) ?
C16 C17 C22 C21 . . . . 178.3(3) ?
C5 C4 C23 C24 . . . . -117.2(4) ?
C3 C4 C23 C24 . . . . 63.9(4) ?
C4 C23 C24 C25 . . . . -177.6(4) ?
C22 C21 C26 C27 . . . . 69.9(8) ?
C20 C21 C26 C27 . . . . -108.2(8) ?
C21 C26 C27 C28 . . . . 60.5(11) ?
C22 C21 C26A C27A . . . . 96.3(12) ?
C20 C21 C26A C27A . . . . -81.1(10) ?
C21 C26A C27A C28A . . . . -61.7(13) ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile and diethyl ether'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DIPEAHPF6
_database_code_depnum_ccdc_archive 'CCDC 2255850'
loop_
_audit_author_name
_audit_author_address
'Diane A. Dickie'
;University of Virginia
United States of America
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 F6 N P'
_chemical_formula_iupac          ?
_chemical_formula_weight         275.22

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   8.2349(2)
_cell_length_b                   17.2894(6)
_cell_length_c                   8.9716(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.3780(10)
_cell_angle_gamma                90
_cell_volume                     1266.77(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9217
_cell_measurement_theta_min      2.5745
_cell_measurement_theta_max      28.2309
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576

_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'HELIOS double bounce multilayer mirror'

_diffrn_measurement_device       'Kappa four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonIII'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            30006
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_full        25.24
_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       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             3123
_reflns_number_gt                2614
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1041
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.078
_refine_ls_number_reflns         3123
_refine_ls_number_parameters     173
_refine_ls_number_restraints     28
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.7824P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.253
_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'
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       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.21872(5) 0.61746(2) 0.69098(4) 0.02402(12) Uani d . . D 1.000000 . .
F F1 0.32063(15) 0.58509(7) 0.56236(12) 0.0428(3) Uani d . . . 1.000000 . .
F F2 0.3063(2) 0.69941(8) 0.6810(2) 0.0571(5) Uani d . P D 0.917(3) A 1
F F3 0.07722(19) 0.64679(9) 0.56646(15) 0.0486(4) Uani d . P D 0.917(3) A 1
F F4 0.11931(17) 0.64943(8) 0.81888(13) 0.0566(4) Uani d . . . 1.000000 . .
F F5 0.13395(18) 0.53660(8) 0.6986(2) 0.0587(5) Uani d . P D 0.917(3) A 1
F F6 0.36459(17) 0.58978(9) 0.81287(13) 0.0473(4) Uani d . P D 0.917(3) A 1
N N1 0.35876(15) 0.63192(7) 0.26193(14) 0.0189(3) Uani d . . . 1.000000 . .
H H1 0.325(2) 0.6302(11) 0.351(2) 0.027(5) Uiso d . . . 1.000000 . .
C C1 0.3460(2) 0.71480(9) 0.20480(19) 0.0258(3) Uani d . . . 1.000000 . .
H H1A 0.457298 0.734870 0.197412 0.031000 Uiso calc U . R 1.000000 . .
H H1B 0.283824 0.715514 0.102765 0.031000 Uiso calc U . R 1.000000 . .
C C2 0.2623(2) 0.76708(10) 0.3064(2) 0.0350(4) Uani d . . . 1.000000 . .
H H2A 0.261140 0.820180 0.268124 0.052000 Uiso calc U . R 1.000000 . .
H H2B 0.321934 0.765548 0.408225 0.052000 Uiso calc U . R 1.000000 . .
H H2C 0.149627 0.749391 0.308872 0.052000 Uiso calc U . R 1.000000 . .
C C3 0.53526(18) 0.60239(10) 0.28336(19) 0.0255(3) Uani d . . . 1.000000 . .
H H3 0.533145 0.547817 0.320010 0.031000 Uiso calc U . R 1.000000 . .
C C4 0.6380(2) 0.64906(12) 0.4036(2) 0.0364(4) Uani d . . . 1.000000 . .
H H4A 0.652266 0.701648 0.366683 0.055000 Uiso calc U . R 1.000000 . .
H H4B 0.745392 0.624507 0.427985 0.055000 Uiso calc U . R 1.000000 . .
H H4C 0.582776 0.651206 0.494020 0.055000 Uiso calc U . R 1.000000 . .
C C5 0.6059(2) 0.60120(12) 0.1354(2) 0.0345(4) Uani d . . . 1.000000 . .
H H5A 0.533312 0.571667 0.061082 0.052000 Uiso calc U . R 1.000000 . .
H H5B 0.714292 0.576880 0.150069 0.052000 Uiso calc U . R 1.000000 . .
H H5C 0.615833 0.654299 0.099402 0.052000 Uiso calc U . R 1.000000 . .
C C6 0.23928(18) 0.57847(9) 0.16707(17) 0.0224(3) Uani d . . . 1.000000 . .
H H6 0.264668 0.579736 0.061046 0.027000 Uiso calc U . R 1.000000 . .
C C7 0.06500(19) 0.60748(11) 0.1694(2) 0.0302(4) Uani d . . . 1.000000 . .
H H7A 0.038113 0.606183 0.272685 0.045000 Uiso calc U . R 1.000000 . .
H H7B -0.011288 0.574249 0.105589 0.045000 Uiso calc U . R 1.000000 . .
H H7C 0.056039 0.660672 0.131530 0.045000 Uiso calc U . R 1.000000 . .
C C8 0.2556(2) 0.49519(9) 0.2240(2) 0.0302(4) Uani d . . . 1.000000 . .
H H8A 0.363339 0.474870 0.208720 0.045000 Uiso calc U . R 1.000000 . .
H H8B 0.169858 0.463303 0.168520 0.045000 Uiso calc U . R 1.000000 . .
H H8C 0.244152 0.493980 0.331388 0.045000 Uiso calc U . R 1.000000 . .
F F3A 0.090(2) 0.5562(10) 0.6057(18) 0.052(3) Uani d . P D 0.083(3) A 2
F F2A 0.157(2) 0.6818(9) 0.5769(16) 0.052(3) Uani d . P D 0.083(3) A 2
F F6A 0.3491(18) 0.6693(10) 0.7763(17) 0.052(3) Uani d . P D 0.083(3) A 2
F F5A 0.271(2) 0.5449(8) 0.7997(16) 0.052(3) Uani d . P D 0.083(3) A 2


_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
P1 F6A . 1.527(12) ?
P1 F2A . 1.553(12) ?
P1 F5 . 1.5679(14) ?
P1 F3 . 1.5901(12) ?
P1 F6 . 1.5908(12) ?
P1 F4 . 1.5917(11) ?
P1 F2 . 1.5979(14) ?
P1 F1 . 1.6118(11) ?
P1 F5A . 1.614(11) ?
P1 F3A . 1.620(12) ?
N1 C1 . 1.5210(19) ?
N1 C6 . 1.5268(18) ?
N1 C3 . 1.5292(19) ?
N1 H1 . 0.88(2) ?
C1 C2 . 1.512(2) ?
C1 H1A . 0.990000 ?
C1 H1B . 0.990000 ?
C2 H2A . 0.980000 ?
C2 H2B . 0.980000 ?
C2 H2C . 0.980000 ?
C3 C4 . 1.516(2) ?
C3 C5 . 1.517(2) ?
C3 H3 . 1.000000 ?
C4 H4A . 0.980000 ?
C4 H4B . 0.980000 ?
C4 H4C . 0.980000 ?
C5 H5A . 0.980000 ?
C5 H5B . 0.980000 ?
C5 H5C . 0.980000 ?
C6 C7 . 1.523(2) ?
C6 C8 . 1.528(2) ?
C6 H6 . 1.000000 ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?
C8 H8A . 0.980000 ?
C8 H8B . 0.980000 ?
C8 H8C . 0.980000 ?

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
F6A P1 F2A . . 93.5(10) ?
F5 P1 F3 . . 91.42(10) ?
F5 P1 F6 . . 90.18(9) ?
F3 P1 F6 . . 178.06(9) ?
F6A P1 F4 . . 80.1(6) ?
F2A P1 F4 . . 94.0(6) ?
F5 P1 F4 . . 90.31(9) ?
F3 P1 F4 . . 89.85(7) ?
F6 P1 F4 . . 91.25(7) ?
F5 P1 F2 . . 179.09(9) ?
F3 P1 F2 . . 88.46(9) ?
F6 P1 F2 . . 89.93(9) ?
F4 P1 F2 . . 90.59(9) ?
F6A P1 F1 . . 99.5(6) ?
F2A P1 F1 . . 86.2(6) ?
F5 P1 F1 . . 89.84(8) ?
F3 P1 F1 . . 90.56(7) ?
F6 P1 F1 . . 88.34(6) ?
F4 P1 F1 . . 179.56(8) ?
F2 P1 F1 . . 89.27(8) ?
F6A P1 F5A . . 92.1(9) ?
F2A P1 F5A . . 174.4(9) ?
F4 P1 F5A . . 87.5(6) ?
F1 P1 F5A . . 92.3(6) ?
F6A P1 F3A . . 175.2(10) ?
F2A P1 F3A . . 90.9(10) ?
F4 P1 F3A . . 101.6(6) ?
F1 P1 F3A . . 78.8(6) ?
F5A P1 F3A . . 83.4(9) ?
C1 N1 C6 . . 111.76(12) ?
C1 N1 C3 . . 112.35(12) ?
C6 N1 C3 . . 113.71(12) ?
C1 N1 H1 . . 108.9(12) ?
C6 N1 H1 . . 103.4(13) ?
C3 N1 H1 . . 106.1(13) ?
C2 C1 N1 . . 112.15(13) ?
C2 C1 H1A . . 109.200000 ?
N1 C1 H1A . . 109.200000 ?
C2 C1 H1B . . 109.200000 ?
N1 C1 H1B . . 109.200000 ?
H1A C1 H1B . . 107.900000 ?
C1 C2 H2A . . 109.500000 ?
C1 C2 H2B . . 109.500000 ?
H2A C2 H2B . . 109.500000 ?
C1 C2 H2C . . 109.500000 ?
H2A C2 H2C . . 109.500000 ?
H2B C2 H2C . . 109.500000 ?
C4 C3 C5 . . 112.86(14) ?
C4 C3 N1 . . 110.27(14) ?
C5 C3 N1 . . 111.09(13) ?
C4 C3 H3 . . 107.500000 ?
C5 C3 H3 . . 107.500000 ?
N1 C3 H3 . . 107.500000 ?
C3 C4 H4A . . 109.500000 ?
C3 C4 H4B . . 109.500000 ?
H4A C4 H4B . . 109.500000 ?
C3 C4 H4C . . 109.500000 ?
H4A C4 H4C . . 109.500000 ?
H4B C4 H4C . . 109.500000 ?
C3 C5 H5A . . 109.500000 ?
C3 C5 H5B . . 109.500000 ?
H5A C5 H5B . . 109.500000 ?
C3 C5 H5C . . 109.500000 ?
H5A C5 H5C . . 109.500000 ?
H5B C5 H5C . . 109.500000 ?
C7 C6 N1 . . 109.51(13) ?
C7 C6 C8 . . 110.39(13) ?
N1 C6 C8 . . 111.17(13) ?
C7 C6 H6 . . 108.600000 ?
N1 C6 H6 . . 108.600000 ?
C8 C6 H6 . . 108.600000 ?
C6 C7 H7A . . 109.500000 ?
C6 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
C6 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?
C6 C8 H8A . . 109.500000 ?
C6 C8 H8B . . 109.500000 ?
H8A C8 H8B . . 109.500000 ?
C6 C8 H8C . . 109.500000 ?
H8A C8 H8C . . 109.500000 ?
H8B C8 H8C . . 109.500000 ?

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
C6 N1 C1 C2 . . . . 106.70(15) ?
C3 N1 C1 C2 . . . . -124.09(15) ?
C1 N1 C3 C4 . . . . 63.63(17) ?
C6 N1 C3 C4 . . . . -168.18(13) ?
C1 N1 C3 C5 . . . . -62.27(17) ?
C6 N1 C3 C5 . . . . 65.92(17) ?
C1 N1 C6 C7 . . . . -58.79(16) ?
C3 N1 C6 C7 . . . . 172.72(13) ?
C1 N1 C6 C8 . . . . 178.97(12) ?
C3 N1 C6 C8 . . . . 50.48(16) ?

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
_geom_hbond_publ_flag
N1 H1 F1 . 0.88(2) 2.06(2) 2.8698(16) 153.9(17) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
