# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1992351'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 F6 N3 P'
_chemical_formula_weight         409.31
_chemical_oxdiff_usercomment     TC559

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'
F F 0.0171 0.0103 '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'

_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'

_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.
;

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                   6.35200(10)
_cell_length_b                   8.22740(10)
_cell_length_c                   33.0348(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.2980(10)
_cell_angle_gamma                90
_cell_volume                     1725.97(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    31725
_cell_measurement_theta_min      3.9440
_cell_measurement_theta_max      50.9210

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.433
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.59562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.550
_oxdiff_exptl_absorpt_empirical_full_max 1.667
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.2(6)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            91442
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -72
_diffrn_reflns_limit_l_max       71
_diffrn_reflns_theta_min         3.956
_diffrn_reflns_theta_max         51.315
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             18826
_reflns_number_gt                12995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0758P)²+0.0677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         18826
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1504
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.61157(7) 0.49713(6) 0.60489(2) 0.01532(7) Uani 1 1 d . . . . .
C2 C 0.46538(7) 0.58718(6) 0.58318(2) 0.01577(7) Uani 1 1 d . . . . .
H2 H 0.337982 0.600297 0.596117 0.019 Uiso 1 1 calc R U . . .
C3 C 0.47280(7) 0.66405(6) 0.54457(2) 0.01541(7) Uani 1 1 d . . . . .
C4 C 0.64655(8) 0.66808(6) 0.51846(2) 0.01669(7) Uani 1 1 d . . . . .
H4 H 0.771175 0.616652 0.526392 0.020 Uiso 1 1 calc R U . . .
C5 C 0.63541(8) 0.74627(7) 0.48165(2) 0.01728(7) Uani 1 1 d . . . . .
H5 H 0.753053 0.747808 0.465395 0.021 Uiso 1 1 calc R U . . .
C6 C 0.44726(8) 0.82483(6) 0.46797(2) 0.01596(7) Uani 1 1 d . . . . .
C7 C 0.27049(8) 0.81743(7) 0.49349(2) 0.01737(8) Uani 1 1 d . . . . .
H7 H 0.144000 0.865230 0.485215 0.021 Uiso 1 1 calc R U . . .
C8 C 0.28518(8) 0.74004(6) 0.53034(2) 0.01679(7) Uani 1 1 d . . . . .
H8 H 0.167403 0.737499 0.546544 0.020 Uiso 1 1 calc R U . . .
C9 C 0.56261(7) 0.41673(6) 0.64287(2) 0.01498(7) Uani 1 1 d . . . . .
C10 C 0.36526(8) 0.43141(6) 0.66123(2) 0.01673(7) Uani 1 1 d . . . . .
H10 H 0.264827 0.502220 0.650356 0.020 Uiso 1 1 calc R U . . .
C11 C 0.32030(8) 0.34196(7) 0.69502(2) 0.01746(7) Uani 1 1 d . . . . .
H11 H 0.188761 0.352282 0.706557 0.021 Uiso 1 1 calc R U . . .
C12 C 0.65630(9) 0.22636(7) 0.69609(2) 0.01963(8) Uani 1 1 d . . . . .
H12 H 0.755071 0.157524 0.708269 0.024 Uiso 1 1 calc R U . . .
C13 C 0.70992(8) 0.31319(7) 0.66229(2) 0.01883(8) Uani 1 1 d . . . . .
H13 H 0.844723 0.303483 0.652143 0.023 Uiso 1 1 calc R U . . .
C14 C 0.81788(8) 0.46573(7) 0.59042(2) 0.01741(8) Uani 1 1 d . . . . .
C15 C 0.24458(10) 0.98432(8) 0.41846(2) 0.02223(9) Uani 1 1 d . . . . .
H15A H 0.132356 0.906631 0.415809 0.033 Uiso 1 1 calc R U . . .
H15B H 0.266375 1.035529 0.392777 0.033 Uiso 1 1 calc R U . . .
H15C H 0.208223 1.065184 0.438048 0.033 Uiso 1 1 calc R U . . .
C16 C 0.62402(10) 0.92058(8) 0.40741(2) 0.02188(9) Uani 1 1 d . . . . .
H16A H 0.728589 0.981160 0.422450 0.033 Uiso 1 1 calc R U . . .
H16B H 0.587782 0.977581 0.382869 0.033 Uiso 1 1 calc R U . . .
H16C H 0.678985 0.815305 0.400908 0.033 Uiso 1 1 calc R U . . .
C17 C 0.40843(11) 0.13978(8) 0.74723(2) 0.02360(10) Uani 1 1 d . . . . .
H17A H 0.461941 0.031583 0.743912 0.035 Uiso 1 1 calc R U . . .
H17B H 0.258104 0.135894 0.749482 0.035 Uiso 1 1 calc R U . . .
H17C H 0.469516 0.187110 0.771323 0.035 Uiso 1 1 calc R U . . .
N1 N 0.43680(8) 0.90189(6) 0.43170(2) 0.01961(7) Uani 1 1 d . . . . .
N2 N 0.98650(8) 0.43263(7) 0.58071(2) 0.02271(9) Uani 1 1 d . . . . .
N3 N 0.46330(7) 0.23916(5) 0.71189(2) 0.01694(7) Uani 1 1 d . . . . .
F1 F 0.28279(7) 0.82438(8) 0.68917(2) 0.03544(11) Uani 1 1 d . . . . .
F2 F 0.00806(9) 0.88878(8) 0.72928(2) 0.03435(11) Uani 1 1 d . . . . .
F3 F 0.00824(9) 0.64963(6) 0.69498(2) 0.03473(11) Uani 1 1 d . . . . .
F4 F -0.21556(6) 0.85149(6) 0.67625(2) 0.02697(8) Uani 1 1 d . . . . .
F5 F 0.05825(8) 0.78601(6) 0.63621(2) 0.02990(9) Uani 1 1 d . . . . .
F6 F 0.05860(7) 1.02553(5) 0.67059(2) 0.02698(8) Uani 1 1 d . . . . .
P1 P 0.03374(2) 0.83715(2) 0.68255(2) 0.01779(3) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3768(7) . ?
C1 C14 1.4286(7) . ?
C1 C9 1.4582(7) . ?
C2 C3 1.4253(7) . ?
C2 H2 0.9300 . ?
C3 C8 1.4166(7) . ?
C3 C4 1.4163(7) . ?
C4 C5 1.3763(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.4232(7) . ?
C5 H5 0.9300 . ?
C6 N1 1.3560(7) . ?
C6 C7 1.4205(7) . ?
C7 C8 1.3751(8) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C13 1.4091(7) . ?
C9 C10 1.4101(7) . ?
C10 C11 1.3727(8) . ?
C10 H10 0.9300 . ?
C11 N3 1.3521(7) . ?
C11 H11 0.9300 . ?
C12 N3 1.3475(7) . ?
C12 C13 1.3748(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N2 1.1574(7) . ?
C15 N1 1.4553(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N1 1.4577(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N3 1.4735(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
F1 P1 1.5955(5) . ?
F2 P1 1.6129(5) . ?
F3 P1 1.6057(5) . ?
F4 P1 1.5969(4) . ?
F5 P1 1.5986(5) . ?
F6 P1 1.6082(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C14 122.41(5) . . ?
C2 C1 C9 122.54(4) . . ?
C14 C1 C9 114.90(4) . . ?
C1 C2 C3 132.02(5) . . ?
C1 C2 H2 114.0 . . ?
C3 C2 H2 114.0 . . ?
C8 C3 C4 116.67(5) . . ?
C8 C3 C2 116.62(4) . . ?
C4 C3 C2 126.68(5) . . ?
C5 C4 C3 121.59(5) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 121.24(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
N1 C6 C7 121.39(5) . . ?
N1 C6 C5 121.12(5) . . ?
C7 C6 C5 117.49(5) . . ?
C8 C7 C6 120.43(5) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C3 122.54(5) . . ?
C7 C8 H8 118.7 . . ?
C3 C8 H8 118.7 . . ?
C13 C9 C10 116.34(5) . . ?
C13 C9 C1 120.91(4) . . ?
C10 C9 C1 122.70(4) . . ?
C11 C10 C9 120.48(5) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
N3 C11 C10 121.36(5) . . ?
N3 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
N3 C12 C13 121.23(5) . . ?
N3 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C9 120.64(5) . . ?
C12 C13 H13 119.7 . . ?
C9 C13 H13 119.7 . . ?
N2 C14 C1 175.44(6) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 N1 C15 120.50(5) . . ?
C6 N1 C16 120.76(5) . . ?
C15 N1 C16 118.34(5) . . ?
C12 N3 C11 119.85(5) . . ?
C12 N3 C17 119.82(5) . . ?
C11 N3 C17 120.33(5) . . ?
F1 P1 F4 179.40(3) . . ?
F1 P1 F5 89.77(3) . . ?
F4 P1 F5 90.71(3) . . ?
F1 P1 F3 90.41(3) . . ?
F4 P1 F3 89.93(3) . . ?
F5 P1 F3 90.26(3) . . ?
F1 P1 F6 89.69(3) . . ?
F4 P1 F6 89.97(2) . . ?
F5 P1 F6 90.35(3) . . ?
F3 P1 F6 179.38(3) . . ?
F1 P1 F2 90.44(3) . . ?
F4 P1 F2 89.07(3) . . ?
F5 P1 F2 179.79(3) . . ?
F3 P1 F2 89.73(3) . . ?
F6 P1 F2 89.66(3) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C3 1.03(9) . . . . ?
C9 C1 C2 C3 -174.31(5) . . . . ?
C1 C2 C3 C8 176.39(5) . . . . ?
C1 C2 C3 C4 -1.59(9) . . . . ?
C8 C3 C4 C5 1.92(8) . . . . ?
C2 C3 C4 C5 179.90(5) . . . . ?
C3 C4 C5 C6 -0.84(8) . . . . ?
C4 C5 C6 N1 179.94(5) . . . . ?
C4 C5 C6 C7 -0.91(8) . . . . ?
N1 C6 C7 C8 -179.34(5) . . . . ?
C5 C6 C7 C8 1.51(8) . . . . ?
C6 C7 C8 C3 -0.40(8) . . . . ?
C4 C3 C8 C7 -1.31(8) . . . . ?
C2 C3 C8 C7 -179.50(5) . . . . ?
C2 C1 C9 C13 173.97(5) . . . . ?
C14 C1 C9 C13 -1.69(7) . . . . ?
C2 C1 C9 C10 -3.12(8) . . . . ?
C14 C1 C9 C10 -178.78(5) . . . . ?
C13 C9 C10 C11 -3.07(8) . . . . ?
C1 C9 C10 C11 174.15(5) . . . . ?
C9 C10 C11 N3 0.71(8) . . . . ?
N3 C12 C13 C9 -0.87(9) . . . . ?
C10 C9 C13 C12 3.15(8) . . . . ?
C1 C9 C13 C12 -174.12(5) . . . . ?
C7 C6 N1 C15 2.05(8) . . . . ?
C5 C6 N1 C15 -178.83(5) . . . . ?
C7 C6 N1 C16 174.72(5) . . . . ?
C5 C6 N1 C16 -6.17(8) . . . . ?
C13 C12 N3 C11 -1.66(9) . . . . ?
C13 C12 N3 C17 177.72(6) . . . . ?
C10 C11 N3 C12 1.74(8) . . . . ?
C10 C11 N3 C17 -177.64(5) . . . . ?

_refine_diff_density_max         0.760
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1992352'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 F6 N3 P'
_chemical_formula_weight         485.40
_chemical_oxdiff_usercomment     'TC374 ASCP REPEAT'

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'
F F 0.0727 0.0534 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   30.1428(6)
_cell_length_b                   6.19510(10)
_cell_length_c                   23.4009(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.329(2)
_cell_angle_gamma                90
_cell_volume                     4362.46(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    13071
_cell_measurement_theta_min      2.8790
_cell_measurement_theta_max      76.8600

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             2000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.736
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.65361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.658
_oxdiff_exptl_absorpt_empirical_full_max 1.783
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27533
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         77.178
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4559
_reflns_number_gt                4181
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+91.5910P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4559
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.1012
_refine_ls_wR_factor_ref         0.2856
_refine_ls_wR_factor_gt          0.2844
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.26153(17) 0.3703(9) 0.8701(2) 0.0246(11) Uani 1 1 d . . . . .
C2 C 0.27147(18) 0.2345(10) 0.8268(2) 0.0267(12) Uani 1 1 d . . . . .
H2 H 0.256058 0.104473 0.826637 0.032 Uiso 1 1 calc R U . . .
C3 C 0.30149(17) 0.2550(9) 0.7812(2) 0.0247(11) Uani 1 1 d . . . . .
C4 C 0.32609(18) 0.4395(10) 0.7678(2) 0.0277(12) Uani 1 1 d . . . . .
H4 H 0.323352 0.564231 0.789430 0.033 Uiso 1 1 calc R U . . .
C5 C 0.35428(19) 0.4395(9) 0.7231(2) 0.0279(12) Uani 1 1 d . . . . .
H5 H 0.369799 0.564554 0.715119 0.033 Uiso 1 1 calc R U . . .
C6 C 0.36000(17) 0.2513(9) 0.6892(2) 0.0239(11) Uani 1 1 d . . . . .
C7 C 0.33566(18) 0.0673(10) 0.7032(2) 0.0275(12) Uani 1 1 d . . . . .
H7 H 0.338722 -0.059052 0.682355 0.033 Uiso 1 1 calc R U . . .
C8 C 0.30742(19) 0.0708(10) 0.7472(2) 0.0279(12) Uani 1 1 d . . . . .
H8 H 0.291553 -0.053584 0.754807 0.034 Uiso 1 1 calc R U . . .
C9 C 0.3984(2) 0.0505(10) 0.6171(3) 0.0316(13) Uani 1 1 d . . . . .
H9A H 0.412405 -0.045223 0.644922 0.047 Uiso 1 1 calc R U . . .
H9B H 0.418342 0.078327 0.587402 0.047 Uiso 1 1 calc R U . . .
H9C H 0.371736 -0.015094 0.600779 0.047 Uiso 1 1 calc R U . . .
C10 C 0.41627(19) 0.4387(10) 0.6365(3) 0.0310(13) Uani 1 1 d . . . . .
H10A H 0.398390 0.563541 0.627333 0.046 Uiso 1 1 calc R U . . .
H10B H 0.435214 0.409719 0.605854 0.046 Uiso 1 1 calc R U . . .
H10C H 0.434156 0.464965 0.671137 0.046 Uiso 1 1 calc R U . . .
C11 C 0.28246(19) 0.5772(10) 0.8764(2) 0.0278(12) Uani 1 1 d . . . . .
C12 C 0.22912(17) 0.3183(9) 0.9136(2) 0.0245(11) Uani 1 1 d . . . . .
C13 C 0.21927(18) 0.4714(10) 0.9549(2) 0.0280(12) Uani 1 1 d . . . . .
H13 H 0.233118 0.605486 0.954783 0.034 Uiso 1 1 calc R U . . .
C14 C 0.18908(18) 0.4266(10) 0.9960(2) 0.0262(11) Uani 1 1 d . . . . .
H14 H 0.183292 0.531112 1.023154 0.031 Uiso 1 1 calc R U . . .
C15 C 0.16736(17) 0.2284(9) 0.9975(2) 0.0229(11) Uani 1 1 d . . . . .
C16 C 0.17735(18) 0.0746(10) 0.9562(2) 0.0260(11) Uani 1 1 d . . . . .
H16 H 0.163321 -0.059073 0.956172 0.031 Uiso 1 1 calc R U . . .
C17 C 0.20776(18) 0.1180(10) 0.9154(2) 0.0270(12) Uani 1 1 d . . . . .
H17 H 0.214025 0.012402 0.888756 0.032 Uiso 1 1 calc R U . . .
C18 C 0.13411(17) 0.1841(9) 1.0400(2) 0.0245(11) Uani 1 1 d . . . . .
C19 C 0.13202(17) 0.3076(9) 1.0900(2) 0.0255(11) Uani 1 1 d . . . . .
H19 H 0.152046 0.419955 1.097060 0.031 Uiso 1 1 calc R U . . .
C20 C 0.10071(18) 0.2637(9) 1.1283(2) 0.0264(11) Uani 1 1 d . . . . .
H20 H 0.099661 0.346924 1.161231 0.032 Uiso 1 1 calc R U . . .
C21 C 0.07225(19) -0.0179(11) 1.0718(3) 0.0333(13) Uani 1 1 d . . . . .
H21 H 0.051473 -0.127723 1.065679 0.040 Uiso 1 1 calc R U . . .
C22 C 0.10307(19) 0.0171(10) 1.0320(3) 0.0313(13) Uani 1 1 d . . . . .
H22 H 0.103391 -0.070066 0.999703 0.038 Uiso 1 1 calc R U . . .
C23 C 0.0367(2) 0.0608(11) 1.1602(3) 0.0352(14) Uani 1 1 d . . . . .
H23A H 0.049720 0.069064 1.198542 0.053 Uiso 1 1 calc R U . . .
H23B H 0.024376 -0.080400 1.153517 0.053 Uiso 1 1 calc R U . . .
H23C H 0.013655 0.167076 1.155053 0.053 Uiso 1 1 calc R U . . .
F1 F 0.46585(14) 0.1253(7) 0.72901(18) 0.0491(11) Uani 1 1 d . . . . .
F2 F 0.48023(19) -0.0567(7) 0.81198(17) 0.0614(14) Uani 1 1 d . . . . .
F4 F 0.53383(19) -0.2403(7) 0.7718(2) 0.0668(15) Uani 1 1 d . . . . .
F7 F 0.48610(12) -0.1641(6) 0.54819(16) 0.0408(9) Uani 1 1 d . . . . .
F8 F 0.44904(12) 0.0186(7) 0.47758(17) 0.0439(10) Uani 1 1 d . . . . .
F9 F 0.50686(14) -0.1987(7) 0.45850(17) 0.0463(10) Uani 1 1 d . . . . .
N1 N 0.38743(15) 0.2528(8) 0.64463(19) 0.0254(10) Uani 1 1 d . . . . .
N2 N 0.29867(18) 0.7452(9) 0.8828(2) 0.0353(12) Uani 1 1 d . . . . .
N3 N 0.07141(15) 0.1022(8) 1.1190(2) 0.0270(10) Uani 1 1 d . . . . .
P1 P 0.500000 -0.0576(4) 0.750000 0.0337(5) Uani 1 2 d S T P . .
P2 P 0.500000 0.000000 0.500000 0.0247(5) Uani 1 2 d S . P . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.363(8) . ?
C1 C11 1.433(8) . ?
C1 C12 1.487(7) . ?
C2 C3 1.445(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.408(8) . ?
C3 C8 1.408(8) . ?
C4 C5 1.384(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.426(8) . ?
C5 H5 0.9300 . ?
C6 N1 1.368(7) . ?
C6 C7 1.405(8) . ?
C7 C8 1.373(8) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 N1 1.456(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N1 1.462(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.156(8) . ?
C12 C13 1.397(8) . ?
C12 C17 1.400(8) . ?
C13 C14 1.391(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.402(8) . ?
C15 C18 1.479(7) . ?
C16 C17 1.388(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C22 1.400(8) . ?
C18 C19 1.401(8) . ?
C19 C20 1.366(8) . ?
C19 H19 0.9300 . ?
C20 N3 1.344(7) . ?
C20 H20 0.9300 . ?
C21 N3 1.334(8) . ?
C21 C22 1.369(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 N3 1.484(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
F1 P1 1.589(4) . ?
F2 P1 1.600(4) . ?
F4 P1 1.587(5) . ?
F7 P2 1.592(4) . ?
F8 P2 1.598(3) . ?
F9 P2 1.589(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C11 120.9(5) . . ?
C2 C1 C12 123.9(5) . . ?
C11 C1 C12 115.3(5) . . ?
C1 C2 C3 132.0(5) . . ?
C1 C2 H2 114.0 . . ?
C3 C2 H2 114.0 . . ?
C4 C3 C8 116.5(5) . . ?
C4 C3 C2 126.6(5) . . ?
C8 C3 C2 116.9(5) . . ?
C5 C4 C3 121.5(5) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
N1 C6 C7 122.0(5) . . ?
N1 C6 C5 121.1(5) . . ?
C7 C6 C5 116.8(5) . . ?
C8 C7 C6 121.1(5) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C3 122.7(5) . . ?
C7 C8 H8 118.6 . . ?
C3 C8 H8 118.6 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C1 178.0(6) . . ?
C13 C12 C17 117.7(5) . . ?
C13 C12 C1 120.0(5) . . ?
C17 C12 C1 122.2(5) . . ?
C14 C13 C12 121.1(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 121.3(5) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 117.5(5) . . ?
C14 C15 C18 121.2(5) . . ?
C16 C15 C18 121.2(5) . . ?
C17 C16 C15 121.3(5) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 121.0(5) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C22 C18 C19 116.9(5) . . ?
C22 C18 C15 121.4(5) . . ?
C19 C18 C15 121.7(5) . . ?
C20 C19 C18 120.3(5) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
N3 C20 C19 121.0(5) . . ?
N3 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
N3 C21 C22 121.4(6) . . ?
N3 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C18 120.1(5) . . ?
C21 C22 H22 120.0 . . ?
C18 C22 H22 120.0 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C6 N1 C9 119.7(5) . . ?
C6 N1 C10 119.6(5) . . ?
C9 N1 C10 117.9(4) . . ?
C21 N3 C20 120.3(5) . . ?
C21 N3 C23 119.3(5) . . ?
C20 N3 C23 120.4(5) . . ?
F4 P1 F4 89.1(4) . 2_656 ?
F4 P1 F1 90.9(2) . 2_656 ?
F4 P1 F1 179.2(3) 2_656 2_656 ?
F4 P1 F1 179.2(3) . . ?
F4 P1 F1 90.9(2) 2_656 . ?
F1 P1 F1 89.1(3) 2_656 . ?
F4 P1 F2 91.6(3) . 2_656 ?
F4 P1 F2 88.7(3) 2_656 2_656 ?
F1 P1 F2 90.5(2) 2_656 2_656 ?
F1 P1 F2 89.2(2) . 2_656 ?
F4 P1 F2 88.7(3) . . ?
F4 P1 F2 91.6(3) 2_656 . ?
F1 P1 F2 89.2(2) 2_656 . ?
F1 P1 F2 90.5(2) . . ?
F2 P1 F2 179.6(3) 2_656 . ?
F9 P2 F9 180.0 . 5_656 ?
F9 P2 F7 90.7(2) . 5_656 ?
F9 P2 F7 89.3(2) 5_656 5_656 ?
F9 P2 F7 89.3(2) . . ?
F9 P2 F7 90.7(2) 5_656 . ?
F7 P2 F7 180.0 5_656 . ?
F9 P2 F8 90.7(2) . . ?
F9 P2 F8 89.3(2) 5_656 . ?
F7 P2 F8 90.5(2) 5_656 . ?
F7 P2 F8 89.5(2) . . ?
F9 P2 F8 89.3(2) . 5_656 ?
F9 P2 F8 90.7(2) 5_656 5_656 ?
F7 P2 F8 89.5(2) 5_656 5_656 ?
F7 P2 F8 90.5(2) . 5_656 ?
F8 P2 F8 180.0(3) . 5_656 ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 0.0(9) . . . . ?
C12 C1 C2 C3 -179.9(5) . . . . ?
C1 C2 C3 C4 -5.9(10) . . . . ?
C1 C2 C3 C8 172.9(6) . . . . ?
C8 C3 C4 C5 0.6(8) . . . . ?
C2 C3 C4 C5 179.4(5) . . . . ?
C3 C4 C5 C6 -0.8(9) . . . . ?
C4 C5 C6 N1 179.1(5) . . . . ?
C4 C5 C6 C7 0.1(8) . . . . ?
N1 C6 C7 C8 -178.3(5) . . . . ?
C5 C6 C7 C8 0.7(8) . . . . ?
C6 C7 C8 C3 -0.9(9) . . . . ?
C4 C3 C8 C7 0.2(8) . . . . ?
C2 C3 C8 C7 -178.6(5) . . . . ?
C2 C1 C12 C13 -176.8(5) . . . . ?
C11 C1 C12 C13 3.3(7) . . . . ?
C2 C1 C12 C17 3.6(8) . . . . ?
C11 C1 C12 C17 -176.3(5) . . . . ?
C17 C12 C13 C14 -0.3(8) . . . . ?
C1 C12 C13 C14 -180.0(5) . . . . ?
C12 C13 C14 C15 -0.4(9) . . . . ?
C13 C14 C15 C16 0.6(8) . . . . ?
C13 C14 C15 C18 -177.8(5) . . . . ?
C14 C15 C16 C17 0.0(8) . . . . ?
C18 C15 C16 C17 178.4(5) . . . . ?
C15 C16 C17 C12 -0.8(8) . . . . ?
C13 C12 C17 C16 0.9(8) . . . . ?
C1 C12 C17 C16 -179.4(5) . . . . ?
C14 C15 C18 C22 160.8(5) . . . . ?
C16 C15 C18 C22 -17.5(8) . . . . ?
C14 C15 C18 C19 -18.8(8) . . . . ?
C16 C15 C18 C19 162.9(5) . . . . ?
C22 C18 C19 C20 -0.1(8) . . . . ?
C15 C18 C19 C20 179.5(5) . . . . ?
C18 C19 C20 N3 0.0(9) . . . . ?
N3 C21 C22 C18 -1.1(10) . . . . ?
C19 C18 C22 C21 0.7(9) . . . . ?
C15 C18 C22 C21 -179.0(6) . . . . ?
C7 C6 N1 C9 -11.4(8) . . . . ?
C5 C6 N1 C9 169.7(5) . . . . ?
C7 C6 N1 C10 -172.1(5) . . . . ?
C5 C6 N1 C10 9.0(8) . . . . ?
C22 C21 N3 C20 1.0(9) . . . . ?
C22 C21 N3 C23 178.7(6) . . . . ?
C19 C20 N3 C21 -0.4(9) . . . . ?
C19 C20 N3 C23 -178.1(5) . . . . ?

_refine_diff_density_max         1.286
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.136

