# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_8910
_database_code_depnum_ccdc_archive 'CCDC 1564412'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT03197A 2017
_audit_update_record             
;
2017-07-25 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
;
 N-methyl-2-pyridyl-triphenylphosphonium tetrafluorborate trifluorosulfonate
;
_chemical_name_common            ?

_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 N P, C F3 O3 S, B F4'
_chemical_formula_sum            'C25 H22 B F7 N O3 P S'
_chemical_formula_weight         591.27

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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 '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                   13.937(4)
_cell_length_b                   10.516(3)
_cell_length_c                   18.021(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.909(7)
_cell_angle_gamma                90
_cell_volume                     2552.5(13)
_cell_formula_units_Z            4


_cell_measurement_temperature    100
_cell_measurement_reflns_used    2077
_cell_measurement_theta_min      3.2814
_cell_measurement_theta_max      41.1910

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.464
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.71829
_exptl_absorpt_correction_T_max  0.95777
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           Cu-K\a
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_detector_area_resol_mean 66.67
_diffrn_reflns_number            31276
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_av_R_equivalents  0.1417
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.281
_diffrn_reflns_theta_max         58.923
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.756
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.756
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.756
_reflns_number_total             3490
_reflns_number_gt                2429
_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       'APEX2 (Bruker AXS, 2005-2013)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2012)'
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.5474 and 1.0000 (SADABS).

#-------------------------------------------------------------------------------

INTENSITY STATISTICS FOR DATASET # 1  8910sadabs.raw

 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma

 Inf - 3.86      63     63    100.0     5.83      79.1   16.31  0.0614  0.0550
3.86 - 2.47     145    145    100.0    10.38      39.8   19.39  0.0758  0.0408
2.47 - 1.93     216    216    100.0    14.85      24.1   21.30  0.0871  0.0372
1.93 - 1.69     203    203    100.0    14.14      17.1   18.38  0.0956  0.0389
1.69 - 1.52     217    217    100.0    13.07      11.9   15.46  0.1200  0.0445
1.52 - 1.41     211    211    100.0    12.58       9.7   14.04  0.1341  0.0504
1.41 - 1.32     213    213    100.0    12.10       8.5   12.30  0.1597  0.0555
1.32 - 1.26     192    192    100.0    11.53       7.9   11.32  0.1701  0.0617
1.26 - 1.20     219    219    100.0    11.01       7.8   10.67  0.1897  0.0656
1.20 - 1.15     226    226    100.0     8.90       6.7    8.17  0.2153  0.0904
1.15 - 1.11     209    209    100.0     7.40       5.0    5.78  0.2779  0.1308
1.11 - 1.07     237    237    100.0     6.99       4.9    5.17  0.3191  0.1468
1.07 - 1.04     204    204    100.0     6.72       3.5    3.79  0.3888  0.1980
1.04 - 1.01     237    238     99.6     6.29       3.9    4.25  0.3730  0.1794
1.01 - 0.99     162    163     99.4     5.94       3.1    3.48  0.4157  0.2288
0.99 - 0.97     177    178     99.4     6.02       2.4    2.99  0.4899  0.2695
0.97 - 0.94     294    305     96.4     4.49       1.9    2.25  0.5404  0.4001
0.94 - 0.92     140    226     61.9     0.77       1.5    0.95  0.4284  0.9383
0.92 - 0.89     224    381     58.8     0.69       1.2    0.79  0.5447  1.1262
0.89 - 0.86     228    411     55.5     0.64       1.3    0.89  0.4248  0.9836
0.86 - 0.84     152    407     37.3     0.42       0.8    0.66  0.5410  1.3983
#------------------------------------------------------------------------------
0.94 - 0.84     744   1425     52.2     0.61       1.2    0.83  0.4790  1.0733
 Inf - 0.84    4169   4864     85.7     6.79       8.8    8.17  0.1366  0.0963

Merged [A],  lowest resolution = 17.41 Angstroms                              

#-------------------------------------------------------------------------------

 Highest peak    0.53  at  0.5467  0.2892  0.0989  [  1.10 A from F5 ]
 Deepest hole   -0.49  at  0.6768  0.5726  0.2119  [  0.97 A from C6 ]
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0941P)²+2.8690P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3490
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1832
_refine_ls_wR_factor_gt          0.1614
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_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 0.3715(3) 0.2096(5) 0.3350(3) 0.0289(12) Uani 1 1 d . . . . .
C2 C 0.4353(3) 0.3024(5) 0.3725(3) 0.0334(13) Uani 1 1 d . . . . .
H2 H 0.4096 0.3747 0.3924 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5380(4) 0.2913(5) 0.3815(3) 0.0385(14) Uani 1 1 d . . . . .
H3 H 0.5819 0.3565 0.4063 0.046 Uiso 1 1 calc R U . . .
C4 C 0.5741(4) 0.1852(5) 0.3541(3) 0.0381(14) Uani 1 1 d . . . . .
H4 H 0.6434 0.1754 0.3599 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5086(4) 0.0924(5) 0.3178(3) 0.0381(13) Uani 1 1 d . . . . .
H5 H 0.5339 0.0179 0.2997 0.046 Uiso 1 1 calc R U . . .
C6 C 0.3457(4) 0.0051(5) 0.2603(3) 0.0368(13) Uani 1 1 d . . . . .
H6A H 0.3216 0.0351 0.2073 0.055 Uiso 1 1 calc R U . . .
H6B H 0.2891 -0.0126 0.2816 0.055 Uiso 1 1 calc R U . . .
H6C H 0.3846 -0.0728 0.2611 0.055 Uiso 1 1 calc R U . . .
C7 C 0.1900(4) 0.1094(5) 0.3692(3) 0.0317(12) Uani 1 1 d . . . . .
C8 C 0.0870(4) 0.1082(5) 0.3615(3) 0.0345(13) Uani 1 1 d . . . . .
H8 H 0.0454 0.1685 0.3292 0.041 Uiso 1 1 calc R U . . .
C9 C 0.0467(4) 0.0194(5) 0.4009(3) 0.0381(13) Uani 1 1 d . . . . .
H9 H -0.0231 0.0169 0.3945 0.046 Uiso 1 1 calc R U . . .
C10 C 0.1072(4) -0.0659(5) 0.4497(3) 0.0364(13) Uani 1 1 d . . . . .
H10 H 0.0789 -0.1267 0.4768 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2095(4) -0.0631(5) 0.4592(3) 0.0350(13) Uani 1 1 d . . . . .
H11 H 0.2509 -0.1212 0.4934 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2513(4) 0.0243(5) 0.4190(3) 0.0330(13) Uani 1 1 d . . . . .
H12 H 0.3211 0.0260 0.4254 0.040 Uiso 1 1 calc R U . . .
C13 C 0.1850(4) 0.2237(5) 0.2178(3) 0.0319(12) Uani 1 1 d . . . . .
C14 C 0.2175(4) 0.3131(5) 0.1719(3) 0.0379(14) Uani 1 1 d . . . . .
H14 H 0.2664 0.3743 0.1946 0.045 Uiso 1 1 calc R U . . .
C15 C 0.1781(4) 0.3116(5) 0.0936(3) 0.0429(15) Uani 1 1 d . . . . .
H15 H 0.1990 0.3730 0.0625 0.051 Uiso 1 1 calc R U . . .
C16 C 0.1087(4) 0.2221(6) 0.0602(3) 0.0437(15) Uani 1 1 d . . . . .
H16 H 0.0807 0.2234 0.0063 0.052 Uiso 1 1 calc R U . . .
C17 C 0.0793(4) 0.1307(5) 0.1044(3) 0.0412(15) Uani 1 1 d . . . . .
H17 H 0.0332 0.0671 0.0806 0.049 Uiso 1 1 calc R U . . .
C18 C 0.1168(4) 0.1310(5) 0.1834(3) 0.0372(14) Uani 1 1 d . . . . .
H18 H 0.0961 0.0683 0.2139 0.045 Uiso 1 1 calc R U . . .
C19 C 0.2169(3) 0.3785(4) 0.3585(3) 0.0301(13) Uani 1 1 d . . . . .
C20 C 0.2408(4) 0.3882(5) 0.4381(3) 0.0359(13) Uani 1 1 d . . . . .
H20 H 0.2710 0.3184 0.4689 0.043 Uiso 1 1 calc R U . . .
C21 C 0.2208(4) 0.4991(5) 0.4725(3) 0.0370(13) Uani 1 1 d . . . . .
H21 H 0.2376 0.5061 0.5269 0.044 Uiso 1 1 calc R U . . .
C22 C 0.1761(4) 0.6002(5) 0.4270(3) 0.0406(14) Uani 1 1 d . . . . .
H22 H 0.1606 0.6756 0.4506 0.049 Uiso 1 1 calc R U . . .
C23 C 0.1541(4) 0.5931(5) 0.3491(3) 0.0412(14) Uani 1 1 d . . . . .
H23 H 0.1257 0.6641 0.3188 0.049 Uiso 1 1 calc R U . . .
C24 C 0.1732(4) 0.4821(5) 0.3139(3) 0.0409(14) Uani 1 1 d . . . . .
H24 H 0.1566 0.4765 0.2594 0.049 Uiso 1 1 calc R U . . .
C25 C 0.4308(4) 0.6851(6) 0.3852(3) 0.0426(14) Uani 1 1 d . . . . .
B1 B 0.8430(4) 0.2725(6) 0.3557(3) 0.0335(15) Uani 1 1 d . . . . .
N1 N 0.4095(3) 0.1048(4) 0.3073(2) 0.0316(10) Uani 1 1 d . . . . .
O1 O 0.5403(2) 0.7978(3) 0.31323(19) 0.0393(9) Uani 1 1 d . . . . .
O2 O 0.6035(3) 0.6111(3) 0.3873(2) 0.0489(10) Uani 1 1 d . . . . .
O3 O 0.5860(3) 0.8088(3) 0.4519(2) 0.0488(10) Uani 1 1 d . . . . .
F1 F 0.7613(2) 0.3434(3) 0.36382(17) 0.0495(8) Uani 1 1 d . . . . .
F2 F 0.8167(2) 0.1447(3) 0.34791(17) 0.0483(8) Uani 1 1 d . . . . .
F3 F 0.9209(2) 0.2913(3) 0.41904(18) 0.0549(9) Uani 1 1 d . . . . .
F4 F 0.8689(3) 0.3142(3) 0.29031(18) 0.0651(10) Uani 1 1 d . . . . .
F5 F 0.3718(2) 0.7829(3) 0.3886(2) 0.0647(10) Uani 1 1 d . . . . .
F6 F 0.4301(2) 0.6102(3) 0.44604(18) 0.0602(10) Uani 1 1 d . . . . .
F7 F 0.3864(2) 0.6171(3) 0.32292(19) 0.0606(10) Uani 1 1 d . . . . .
P1 P 0.23784(9) 0.22944(12) 0.31869(7) 0.0313(4) Uani 1 1 d . . . . .
S1 S 0.55446(10) 0.73162(13) 0.38472(8) 0.0432(5) 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 N1 1.370(6) . ?
C1 C2 1.374(7) . ?
C1 P1 1.822(5) . ?
C2 C3 1.403(7) . ?
C3 C4 1.368(7) . ?
C4 C5 1.380(7) . ?
C5 N1 1.352(6) . ?
C6 N1 1.490(6) . ?
C7 C12 1.393(7) . ?
C7 C8 1.406(7) . ?
C7 P1 1.784(5) . ?
C8 C9 1.378(7) . ?
C9 C10 1.381(7) . ?
C10 C11 1.393(7) . ?
C11 C12 1.387(7) . ?
C13 C18 1.391(7) . ?
C13 C14 1.403(7) . ?
C13 P1 1.779(5) . ?
C14 C15 1.375(7) . ?
C15 C16 1.372(8) . ?
C16 C17 1.376(7) . ?
C17 C18 1.385(7) . ?
C19 C20 1.390(7) . ?
C19 C24 1.398(7) . ?
C19 P1 1.779(5) . ?
C20 C21 1.383(7) . ?
C21 C22 1.390(7) . ?
C22 C23 1.359(7) . ?
C23 C24 1.387(7) . ?
C25 F5 1.329(6) . ?
C25 F7 1.340(6) . ?
C25 F6 1.352(6) . ?
C25 S1 1.794(5) . ?
B1 F3 1.373(7) . ?
B1 F4 1.390(7) . ?
B1 F2 1.390(7) . ?
B1 F1 1.400(6) . ?
O1 S1 1.433(3) . ?
O2 S1 1.435(4) . ?
O3 S1 1.430(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
N1 C1 C2 119.2(4) . . ?
N1 C1 P1 120.5(3) . . ?
C2 C1 P1 120.2(4) . . ?
C1 C2 C3 120.7(5) . . ?
C4 C3 C2 118.9(5) . . ?
C3 C4 C5 119.3(5) . . ?
N1 C5 C4 121.6(5) . . ?
C12 C7 C8 119.9(4) . . ?
C12 C7 P1 122.4(4) . . ?
C8 C7 P1 117.5(4) . . ?
C9 C8 C7 119.7(5) . . ?
C8 C9 C10 120.4(5) . . ?
C9 C10 C11 120.2(5) . . ?
C12 C11 C10 120.2(5) . . ?
C11 C12 C7 119.5(5) . . ?
C18 C13 C14 119.7(5) . . ?
C18 C13 P1 122.3(4) . . ?
C14 C13 P1 118.0(4) . . ?
C15 C14 C13 119.5(5) . . ?
C16 C15 C14 120.6(5) . . ?
C15 C16 C17 120.4(5) . . ?
C16 C17 C18 120.3(5) . . ?
C17 C18 C13 119.5(5) . . ?
C20 C19 C24 119.3(5) . . ?
C20 C19 P1 117.4(4) . . ?
C24 C19 P1 123.2(4) . . ?
C21 C20 C19 120.2(5) . . ?
C20 C21 C22 119.5(5) . . ?
C23 C22 C21 121.0(5) . . ?
C22 C23 C24 120.1(5) . . ?
C23 C24 C19 119.9(5) . . ?
F5 C25 F7 107.2(4) . . ?
F5 C25 F6 106.2(4) . . ?
F7 C25 F6 105.7(4) . . ?
F5 C25 S1 113.3(4) . . ?
F7 C25 S1 112.2(4) . . ?
F6 C25 S1 111.7(4) . . ?
F3 B1 F4 109.7(5) . . ?
F3 B1 F2 110.8(4) . . ?
F4 B1 F2 109.8(5) . . ?
F3 B1 F1 109.1(4) . . ?
F4 B1 F1 108.4(4) . . ?
F2 B1 F1 109.0(4) . . ?
C5 N1 C1 120.2(4) . . ?
C5 N1 C6 116.7(4) . . ?
C1 N1 C6 122.9(4) . . ?
C19 P1 C13 112.0(2) . . ?
C19 P1 C7 107.2(2) . . ?
C13 P1 C7 112.8(2) . . ?
C19 P1 C1 107.6(2) . . ?
C13 P1 C1 107.3(2) . . ?
C7 P1 C1 109.7(2) . . ?
O3 S1 O1 115.3(2) . . ?
O3 S1 O2 115.7(2) . . ?
O1 S1 O2 114.4(2) . . ?
O3 S1 C25 103.7(2) . . ?
O1 S1 C25 103.1(2) . . ?
O2 S1 C25 102.1(3) . . ?

_refine_diff_density_max         0.529
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.129

_shelxl_version_number           2014/6



_audit_creation_date             2014-08-05
_audit_block_code                GAA-GA-178-01
_chemical_compound_source        acetonitrile

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'p 21/c'
_symmetry_space_group_name_Hall  '-p 2ybc'
_symmetry_Int_Tables_number      14

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 1.00 1.00 0.0100
2.00 -1.00 -1.00 0.0100
0.00 1.00 -1.00 0.1100
0.00 -1.00 1.00 0.1100
0.00 -1.00 -2.00 0.0150
0.00 1.00 2.00 0.0150
_diffrn_radiation_monochromator  'MONTEL graded multilayer optic'
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;

####################################################################### 
# 
# 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_9146sadabs
_database_code_depnum_ccdc_archive 'CCDC 1564415'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT03197A 2017
_audit_update_record             
;
2017-07-25 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_block_code                GAA-GA-293-01
_audit_creation_date             2015-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 Title
;
_chemical_formula_moiety         '2(C F3 O3 S), C24 H22 N P'
_chemical_formula_sum            'C26 H22 F6 N O6 P S2'
_chemical_formula_weight         653.53
_chemical_compound_source        acetonitrile
_chemical_melting_point          ?
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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-p 2yn'
_symmetry_Int_Tables_number      14

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                   9.4391(3)
_cell_length_b                   10.3400(4)
_cell_length_c                   28.9765(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.4003(10)
_cell_angle_gamma                90
_cell_volume                     2819.78(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9901


_cell_measurement_temperature    100
_cell_measurement_theta_max      67.1951
_cell_measurement_theta_min      4.5419
_shelx_estimated_absorpt_T_max   0.755
_shelx_estimated_absorpt_T_min   0.476
_exptl_absorpt_coefficient_mu    3.001
_exptl_absorpt_correction_T_max  0.84597
_exptl_absorpt_correction_T_min  0.61922

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0600
0.00 0.00 1.00 0.0600
0.00 1.00 0.00 0.1450
0.00 -1.00 0.00 0.1250
1.00 0.00 0.00 0.0500
-1.00 0.00 0.00 0.0500
-1.00 0.00 1.00 0.0350
1.00 0.00 -1.00 0.0450
0.00 1.00 -1.00 0.1300

_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            65121
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.808
_diffrn_reflns_theta_min         3.059
_diffrn_radiation_monochromator  'MONTEL graded multilayer optic'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4714
_reflns_number_total             5075
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'

_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5075
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+2.6441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1001

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.6016 and 0.8572 (SADABS).

Highest peak        ?
Deepest hole        ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
  C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.28170(5) 0.33069(4) 0.61682(2) 0.01860(13) Uani 1 1 d . . . . .
S2 S 0.46681(5) 0.66154(5) 0.71915(2) 0.02166(13) Uani 1 1 d . . . . .
F1 F 0.12710(13) 0.20773(13) 0.55096(4) 0.0314(3) Uani 1 1 d . . . . .
F2 F 0.34998(14) 0.21894(13) 0.53987(4) 0.0343(3) Uani 1 1 d . . . . .
F3 F 0.27761(12) 0.08741(11) 0.59091(4) 0.0253(3) Uani 1 1 d . . . . .
F4 F 0.66739(17) 0.83331(17) 0.71287(6) 0.0557(5) Uani 1 1 d . . . . .
F5 F 0.74016(15) 0.65460(18) 0.74270(7) 0.0626(5) Uani 1 1 d . . . . .
F6 F 0.62516(17) 0.78962(19) 0.78237(5) 0.0568(4) Uani 1 1 d . . . . .
O1 O 0.17333(14) 0.29971(14) 0.64762(5) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.25944(16) 0.44913(14) 0.59130(5) 0.0280(3) Uani 1 1 d . . . . .
O3 O 0.42504(14) 0.30654(14) 0.63564(5) 0.0245(3) Uani 1 1 d . . . . .
O4 O 0.49134(18) 0.6315(2) 0.67221(6) 0.0440(4) Uani 1 1 d . . . . .
O5 O 0.45342(18) 0.55372(16) 0.74952(7) 0.0441(4) Uani 1 1 d . . . . .
O6 O 0.36305(15) 0.76171(14) 0.72399(5) 0.0279(3) Uani 1 1 d . . . . .
C25 C 0.2581(2) 0.2060(2) 0.57245(7) 0.0213(4) Uani 1 1 d . . . . .
C26 C 0.6324(2) 0.7383(2) 0.74066(8) 0.0336(5) Uani 1 1 d . . . . .
P1 P 0.03466(5) 0.23606(5) 0.39097(2) 0.01528(12) Uani 1 1 d . . . . .
N1 N -0.10273(16) 0.38534(16) 0.24693(5) 0.0181(3) Uani 1 1 d . . . . .
C1 C -0.02274(19) 0.29093(18) 0.33307(6) 0.0163(4) Uani 1 1 d . . . . .
C2 C -0.0649(2) 0.41961(19) 0.32751(6) 0.0193(4) Uani 1 1 d . . . . .
H2 H -0.0655 0.4754 0.3535 0.023 Uiso 1 1 calc R . . . .
C3 C -0.1057(2) 0.46472(19) 0.28370(6) 0.0189(4) Uani 1 1 d . . . . .
H3 H -0.1359 0.5518 0.2795 0.023 Uiso 1 1 calc R . . . .
C4 C -0.0643(2) 0.26058(18) 0.25166(7) 0.0182(4) Uani 1 1 d . . . . .
H4 H -0.0659 0.2064 0.2251 0.022 Uiso 1 1 calc R . . . .
C5 C -0.02250(19) 0.21051(19) 0.29469(6) 0.0181(4) Uani 1 1 d . . . . .
H5 H 0.0059 0.1226 0.2980 0.022 Uiso 1 1 calc R . . . .
C6 C -0.1502(2) 0.4350(2) 0.20033(6) 0.0241(4) Uani 1 1 d . . . . .
H6A H -0.2472 0.4052 0.1918 0.036 Uiso 1 1 calc GR . . . .
H6B H -0.0866 0.4028 0.1777 0.036 Uiso 1 1 calc GR . . . .
H6C H -0.1483 0.5297 0.2007 0.036 Uiso 1 1 calc GR . . . .
C7 C -0.11718(19) 0.20821(18) 0.42293(6) 0.0174(4) Uani 1 1 d . . . . .
C8 C -0.0961(2) 0.14349(19) 0.46532(7) 0.0200(4) Uani 1 1 d . . . . .
H8 H -0.0043 0.1127 0.4757 0.024 Uiso 1 1 calc R . . . .
C9 C -0.2096(2) 0.1247(2) 0.49201(7) 0.0244(4) Uani 1 1 d . . . . .
H9 H -0.1959 0.0812 0.5209 0.029 Uiso 1 1 calc R . . . .
C10 C -0.3439(2) 0.1694(2) 0.47649(8) 0.0263(5) Uani 1 1 d . . . . .
H10 H -0.4220 0.1557 0.4947 0.032 Uiso 1 1 calc R . . . .
C11 C -0.3641(2) 0.2336(2) 0.43477(8) 0.0258(5) Uani 1 1 d . . . . .
H11 H -0.4562 0.2643 0.4247 0.031 Uiso 1 1 calc R . . . .
C12 C -0.2516(2) 0.25388(18) 0.40733(7) 0.0210(4) Uani 1 1 d . . . . .
H12 H -0.2659 0.2979 0.3786 0.025 Uiso 1 1 calc R . . . .
C13 C 0.13211(19) 0.08797(18) 0.38799(6) 0.0170(4) Uani 1 1 d . . . . .
C14 C 0.0579(2) -0.02673(19) 0.37802(7) 0.0211(4) Uani 1 1 d . . . . .
H14 H -0.0428 -0.0258 0.3734 0.025 Uiso 1 1 calc R . . . .
C15 C 0.1316(2) -0.1420(2) 0.37494(7) 0.0243(4) Uani 1 1 d . . . . .
H15 H 0.0813 -0.2202 0.3682 0.029 Uiso 1 1 calc R . . . .
C16 C 0.2787(2) -0.1431(2) 0.38163(7) 0.0258(4) Uani 1 1 d . . . . .
H16 H 0.3292 -0.2220 0.3792 0.031 Uiso 1 1 calc R . . . .
C17 C 0.3522(2) -0.0296(2) 0.39187(7) 0.0275(5) Uani 1 1 d . . . . .
H17 H 0.4529 -0.0312 0.3967 0.033 Uiso 1 1 calc R . . . .
C18 C 0.2800(2) 0.0862(2) 0.39516(7) 0.0232(4) Uani 1 1 d . . . . .
H18 H 0.3308 0.1639 0.4023 0.028 Uiso 1 1 calc R . . . .
C19 C 0.14593(19) 0.36121(18) 0.41607(6) 0.0172(4) Uani 1 1 d . . . . .
C20 C 0.2549(2) 0.40770(19) 0.39022(7) 0.0208(4) Uani 1 1 d . . . . .
H20 H 0.2629 0.3779 0.3595 0.025 Uiso 1 1 calc R . . . .
C21 C 0.3508(2) 0.49717(19) 0.40964(7) 0.0238(4) Uani 1 1 d . . . . .
H21 H 0.4252 0.5286 0.3924 0.029 Uiso 1 1 calc R . . . .
C22 C 0.3377(2) 0.5409(2) 0.45433(7) 0.0258(4) Uani 1 1 d . . . . .
H22 H 0.4044 0.6015 0.4677 0.031 Uiso 1 1 calc R . . . .
C23 C 0.2288(2) 0.4972(2) 0.47974(7) 0.0257(4) Uani 1 1 d . . . . .
H23 H 0.2200 0.5293 0.5101 0.031 Uiso 1 1 calc R . . . .
C24 C 0.1321(2) 0.40636(19) 0.46078(6) 0.0211(4) Uani 1 1 d . . . . .
H24 H 0.0577 0.3756 0.4781 0.025 Uiso 1 1 calc R . . . .


_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
S1 O1 1.4441(14) . ?
S1 O2 1.4376(15) . ?
S1 O3 1.4413(14) . ?
S1 C25 1.822(2) . ?
S2 O4 1.4312(17) . ?
S2 O5 1.4321(17) . ?
S2 O6 1.4397(15) . ?
S2 C26 1.820(2) . ?
F1 C25 1.342(2) . ?
F2 C25 1.336(2) . ?
F3 C25 1.345(2) . ?
F4 C26 1.328(3) . ?
F5 C26 1.334(3) . ?
F6 C26 1.326(3) . ?
P1 C1 1.8140(19) . ?
P1 C7 1.7884(19) . ?
P1 C13 1.7917(19) . ?
P1 C19 1.7859(19) . ?
N1 C3 1.347(2) . ?
N1 C4 1.344(3) . ?
N1 C6 1.482(2) . ?
C1 C2 1.395(3) . ?
C1 C5 1.389(3) . ?
C2 C3 1.379(3) . ?
C4 C5 1.379(3) . ?
C7 C8 1.400(3) . ?
C7 C12 1.396(3) . ?
C8 C9 1.382(3) . ?
C9 C10 1.391(3) . ?
C10 C11 1.380(3) . ?
C11 C12 1.391(3) . ?
C13 C14 1.396(3) . ?
C13 C18 1.396(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.383(3) . ?
C17 C18 1.385(3) . ?
C19 C20 1.403(3) . ?
C19 C24 1.393(3) . ?
C20 C21 1.383(3) . ?
C21 C22 1.386(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.393(3) . ?

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
O1 S1 C25 103.02(9) . . ?
O2 S1 O1 115.11(9) . . ?
O2 S1 O3 115.99(9) . . ?
O2 S1 C25 103.57(9) . . ?
O3 S1 O1 114.62(8) . . ?
O3 S1 C25 101.80(9) . . ?
O4 S2 O5 116.31(12) . . ?
O4 S2 O6 114.19(10) . . ?
O4 S2 C26 102.89(11) . . ?
O5 S2 O6 114.04(10) . . ?
O5 S2 C26 104.07(11) . . ?
O6 S2 C26 103.03(11) . . ?
F1 C25 S1 112.11(14) . . ?
F1 C25 F3 106.83(16) . . ?
F2 C25 S1 112.16(14) . . ?
F2 C25 F1 107.21(16) . . ?
F2 C25 F3 107.21(16) . . ?
F3 C25 S1 111.03(13) . . ?
F4 C26 S2 111.23(15) . . ?
F4 C26 F5 106.39(19) . . ?
F5 C26 S2 111.35(18) . . ?
F6 C26 S2 112.59(16) . . ?
F6 C26 F4 106.8(2) . . ?
F6 C26 F5 108.15(19) . . ?
C7 P1 C1 109.56(9) . . ?
C7 P1 C13 108.79(9) . . ?
C13 P1 C1 109.93(8) . . ?
C19 P1 C1 105.94(9) . . ?
C19 P1 C7 112.05(9) . . ?
C19 P1 C13 110.54(9) . . ?
C3 N1 C6 119.12(16) . . ?
C4 N1 C3 121.74(16) . . ?
C4 N1 C6 119.06(16) . . ?
C2 C1 P1 117.88(14) . . ?
C5 C1 P1 122.31(15) . . ?
C5 C1 C2 119.79(17) . . ?
C3 C2 C1 119.08(17) . . ?
N1 C3 C2 120.04(18) . . ?
N1 C4 C5 120.57(17) . . ?
C4 C5 C1 118.76(18) . . ?
C8 C7 P1 117.76(14) . . ?
C12 C7 P1 121.50(15) . . ?
C12 C7 C8 120.69(18) . . ?
C9 C8 C7 119.62(18) . . ?
C8 C9 C10 119.89(19) . . ?
C11 C10 C9 120.33(19) . . ?
C10 C11 C12 120.86(19) . . ?
C11 C12 C7 118.62(19) . . ?
C14 C13 P1 119.00(14) . . ?
C18 C13 P1 121.02(15) . . ?
C18 C13 C14 119.97(18) . . ?
C15 C14 C13 119.86(18) . . ?
C14 C15 C16 119.97(19) . . ?
C17 C16 C15 120.19(19) . . ?
C16 C17 C18 120.48(19) . . ?
C17 C18 C13 119.51(19) . . ?
C20 C19 P1 117.60(14) . . ?
C24 C19 P1 121.85(15) . . ?
C24 C19 C20 120.42(17) . . ?
C21 C20 C19 119.70(18) . . ?
C20 C21 C22 119.73(19) . . ?
C23 C22 C21 120.88(19) . . ?
C22 C23 C24 120.03(19) . . ?
C19 C24 C23 119.21(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'


_shelxl_version_number           2014-3
####################################################################### 
# 
# 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_8486sadabs
_database_code_depnum_ccdc_archive 'CCDC 1564413'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT03197A 2017
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_block_code                GAA-GA-006
_audit_creation_date             2013-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;

_chemical_compound_source        dichlormethane
_chemical_name_common            ?
_chemical_name_systematic        
;
 Title
;
_chemical_formula_moiety         'C34 H45 N2 P, 2(B F4)'
_chemical_formula_sum            'C34 H45 B2 F8 N2 P'
_chemical_formula_weight         686.31
_chemical_absolute_configuration rmad

_chemical_melting_point          ?
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'
B B 0.0090 0.0039 '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'

_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_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   Cc
_symmetry_space_group_name_Hall  'c -2yc'
_symmetry_Int_Tables_number      9

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'

_cell_length_a                   14.2328(7)
_cell_length_b                   14.8040(7)
_cell_length_c                   16.3008(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.5451(18)
_cell_angle_gamma                90
_cell_volume                     3431.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9931


_cell_measurement_temperature    100
_cell_measurement_theta_max      67.2271
_cell_measurement_theta_min      2.7134
_shelx_estimated_absorpt_T_max   0.816
_shelx_estimated_absorpt_T_min   0.424
_exptl_absorpt_coefficient_mu    1.327
_exptl_absorpt_correction_T_max  0.84009
_exptl_absorpt_correction_T_min  0.61478

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.00 2.00 -1.00 0.0700
-2.00 -2.00 1.00 0.0800
-1.00 -1.00 0.00 0.1100
0.00 1.00 3.00 0.2900
1.00 -1.00 -1.00 0.1000
-2.00 2.00 1.00 0.1000
-1.00 1.00 0.00 0.1000
2.00 1.00 -2.00 0.0600
2.00 2.00 1.00 0.2300
0.00 0.00 1.00 0.3310
1.00 -1.00 0.00 0.2000

_exptl_crystal_description       needle
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39935
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.690
_diffrn_reflns_theta_min         4.311
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.746
_reflns_number_gt                5225
_reflns_number_total             5328
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'

_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         5328
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0768
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1575P)²+3.5778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2017

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.5661 and 0.9569 (SADABS).

 Due to disorder of the N-isopropyl groups a lower precission of all bond lengths 
 and angles expressed by higher standsrd uncertainties is observed.The bond 
 lengths and angles in the structure around the three-membered ring are 
 less reliable

Highest peak        ?
Deepest hole        ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F8A(0.5) F8B(0.5) N1A(0.6) N1B(0.4) C4A(0.6) H4A(0.6) C4B(0.4)
 H4B(0.4) C5A(0.6) H5AA(0.6) H5AB(0.6) H5AC(0.6) C5B(0.4) H5BA(0.4) H5BB(0.4)
 H5BC(0.4) C6A(0.6) H6AA(0.6) H6AB(0.6) H6AC(0.6) C6B(0.4) H6BA(0.4) H6BB(0.4)
 H6BC(0.4) C7A(0.6) H7A(0.6) C7B(0.4) H7B(0.4) C8A(0.6) H8AA(0.6) H8AB(0.6)
 H8AC(0.6) C8B(0.4) H8BA(0.4) H8BB(0.4) H8BC(0.4) C9A(0.6) H9AA(0.6) H9AB(0.6)
 H9AC(0.6) C9B(0.4) H9BA(0.4) H9BB(0.4) H9BC(0.4) C10A(0.5) H10A(0.5) C10B(0.5)
 H10B(0.5) C11A(0.5) H11A(0.5) H11B(0.5) H11C(0.5) C11B(0.5) H11D(0.5)
 H11E(0.5) H11F(0.5) C12A(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C12B(0.5)
 H12D(0.5) H12E(0.5) H12F(0.5)
3.a Ternary CH refined with riding coordinates:
 C4A(H4A), C4B(H4B), C7A(H7A), C7B(H7B), C10A(H10A), C10B(H10B), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
3.d Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C5B(H5BA,H5BB,H5BC), C6A(H6AA,H6AB,H6AC), C6B(H6BA,H6BB,
 H6BC), C8A(H8AA,H8AB,H8AC), C8B(H8BA,H8BB,H8BC), C9A(H9AA,H9AB,H9AC), C9B(H9BA,
 H9BB,H9BC), C11A(H11A,H11B,H11C), C11B(H11D,H11E,H11F), C12A(H12A,H12B,H12C),
 C12B(H12D,H12E,H12F), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
P1 P 0.54117(8) 0.31946(7) 0.29995(8) 0.0214(3) Uani 1 1 d . . . . .
F1 F -0.0411(3) 0.5584(3) 0.4661(3) 0.0532(11) Uani 1 1 d . . . . .
F2 F 0.0930(3) 0.6043(3) 0.4106(3) 0.0459(10) Uani 1 1 d . . . . .
F3 F 0.0289(3) 0.4697(3) 0.3736(3) 0.0544(12) Uani 1 1 d . . . . .
F4 F 0.0995(3) 0.4888(3) 0.5010(3) 0.0542(12) Uani 1 1 d . . . . .
F5 F 0.4504(4) 0.4836(4) 0.5099(3) 0.0676(13) Uani 1 1 d . . . . .
F6 F 0.5813(4) 0.5040(3) 0.4414(3) 0.0596(12) Uani 1 1 d . . . . .
F7 F 0.5711(4) 0.5575(4) 0.5721(3) 0.0652(13) Uani 1 1 d . . . . .
F8A F 0.5053(9) 0.6278(7) 0.4616(7) 0.059(3) Uiso 0.5 1 d . . P A 1
F8B F 0.4709(10) 0.6205(8) 0.4726(7) 0.061(3) Uiso 0.5 1 d . . P A 2
N1A N 0.5880(7) 0.2853(5) 0.5379(5) 0.0245(18) Uiso 0.6 1 d . . P B 1
N1B N 0.5537(10) 0.2912(8) 0.5489(8) 0.024(3) Uiso 0.4 1 d . . P B 2
N2 N 0.3335(4) 0.2549(3) 0.4516(3) 0.0358(12) Uani 1 1 d . . . . .
C1 C 0.4959(4) 0.2964(3) 0.3970(4) 0.0246(11) Uani 1 1 d . . . . .
C2 C 0.5139(5) 0.2872(3) 0.4807(4) 0.0329(13) Uani 1 1 d . . . . .
C3 C 0.4214(4) 0.2741(3) 0.4454(3) 0.0268(11) Uani 1 1 d . . . . .
C4A C 0.6864(9) 0.3031(7) 0.5170(8) 0.030(2) Uiso 0.6 1 d . . P B 1
H4A H 0.6847 0.3175 0.4571 0.036 Uiso 0.6 1 calc R U P B 1
C4B C 0.6570(15) 0.3152(11) 0.5355(12) 0.035(4) Uiso 0.4 1 d . . P B 2
H4B H 0.6577 0.3447 0.4803 0.042 Uiso 0.4 1 calc R U P B 2
C5A C 0.7279(9) 0.3853(8) 0.5610(10) 0.044(3) Uiso 0.6 1 d . . P B 1
H5AA H 0.7460 0.3693 0.6179 0.066 Uiso 0.6 1 calc R U P B 1
H5AB H 0.6811 0.4338 0.5606 0.066 Uiso 0.6 1 calc R U P B 1
H5AC H 0.7835 0.4058 0.5329 0.066 Uiso 0.6 1 calc R U P B 1
C5B C 0.7048(17) 0.3830(15) 0.5969(18) 0.058(5) Uiso 0.4 1 d . . P B 2
H5BA H 0.6626 0.4343 0.6049 0.087 Uiso 0.4 1 calc R U P B 2
H5BB H 0.7636 0.4048 0.5749 0.087 Uiso 0.4 1 calc R U P B 2
H5BC H 0.7182 0.3528 0.6496 0.087 Uiso 0.4 1 calc R U P B 2
C6A C 0.7496(12) 0.2213(10) 0.5287(9) 0.045(3) Uiso 0.6 1 d . . P B 1
H6AA H 0.8124 0.2356 0.5101 0.067 Uiso 0.6 1 calc R U P B 1
H6AB H 0.7232 0.1706 0.4966 0.067 Uiso 0.6 1 calc R U P B 1
H6AC H 0.7540 0.2048 0.5870 0.067 Uiso 0.6 1 calc R U P B 1
C6B C 0.718(2) 0.2303(19) 0.5297(18) 0.063(7) Uiso 0.4 1 d . . P B 2
H6BA H 0.7281 0.2039 0.5845 0.094 Uiso 0.4 1 calc R U P B 2
H6BB H 0.7787 0.2464 0.5077 0.094 Uiso 0.4 1 calc R U P B 2
H6BC H 0.6859 0.1863 0.4933 0.094 Uiso 0.4 1 calc R U P B 2
C7A C 0.5716(7) 0.2637(6) 0.6254(6) 0.0310(19) Uiso 0.6 1 d . . P B 1
H7A H 0.6355 0.2635 0.6534 0.037 Uiso 0.6 1 calc R U P B 1
C7B C 0.5167(10) 0.2687(9) 0.6294(9) 0.027(3) Uiso 0.4 1 d . . P B 2
H7B H 0.4486 0.2546 0.6186 0.032 Uiso 0.4 1 calc R U P B 2
C8A C 0.5335(7) 0.1672(7) 0.6368(7) 0.030(2) Uiso 0.6 1 d . . P B 1
H8AA H 0.5253 0.1560 0.6953 0.045 Uiso 0.6 1 calc R U P B 1
H8AB H 0.5781 0.1234 0.6159 0.045 Uiso 0.6 1 calc R U P B 1
H8AC H 0.4727 0.1610 0.6066 0.045 Uiso 0.6 1 calc R U P B 1
C8B C 0.5592(15) 0.1855(13) 0.6673(14) 0.047(4) Uiso 0.4 1 d . . P B 2
H8BA H 0.5508 0.1348 0.6291 0.070 Uiso 0.4 1 calc R U P B 2
H8BB H 0.5283 0.1717 0.7183 0.070 Uiso 0.4 1 calc R U P B 2
H8BC H 0.6265 0.1955 0.6793 0.070 Uiso 0.4 1 calc R U P B 2
C9A C 0.5171(11) 0.3388(11) 0.6680(12) 0.041(4) Uiso 0.6 1 d . . P B 1
H9AA H 0.4561 0.3479 0.6389 0.061 Uiso 0.6 1 calc R U P B 1
H9AB H 0.5533 0.3950 0.6674 0.061 Uiso 0.6 1 calc R U P B 1
H9AC H 0.5072 0.3212 0.7250 0.061 Uiso 0.6 1 calc R U P B 1
C9B C 0.520(2) 0.347(2) 0.688(2) 0.058(10) Uiso 0.4 1 d . . P B 2
H9BA H 0.5838 0.3549 0.7116 0.087 Uiso 0.4 1 calc R U P B 2
H9BB H 0.4767 0.3361 0.7323 0.087 Uiso 0.4 1 calc R U P B 2
H9BC H 0.5004 0.4026 0.6587 0.087 Uiso 0.4 1 calc R U P B 2
C10A C 0.2709(10) 0.2319(9) 0.5198(9) 0.036(3) Uiso 0.5 1 d . . P C 1
H10A H 0.2070 0.2189 0.4945 0.043 Uiso 0.5 1 calc R U P C 1
C10B C 0.3103(7) 0.2495(6) 0.5444(6) 0.0158(18) Uiso 0.5 1 d . . P C 2
H10B H 0.3714 0.2462 0.5770 0.019 Uiso 0.5 1 calc R U P C 2
C11A C 0.2620(18) 0.3169(17) 0.5739(16) 0.050(9) Uiso 0.5 1 d . . P C 1
H11A H 0.3249 0.3386 0.5911 0.074 Uiso 0.5 1 calc R U P C 1
H11B H 0.2270 0.3019 0.6224 0.074 Uiso 0.5 1 calc R U P C 1
H11C H 0.2286 0.3643 0.5423 0.074 Uiso 0.5 1 calc R U P C 1
C11B C 0.2613(11) 0.3337(13) 0.5695(10) 0.024(5) Uiso 0.5 1 d . . P C 2
H11D H 0.2961 0.3866 0.5509 0.036 Uiso 0.5 1 calc R U P C 2
H11E H 0.2584 0.3353 0.6294 0.036 Uiso 0.5 1 calc R U P C 2
H11F H 0.1974 0.3346 0.5446 0.036 Uiso 0.5 1 calc R U P C 2
C12A C 0.3042(12) 0.1483(10) 0.5620(10) 0.045(3) Uiso 0.5 1 d . . P C 1
H12A H 0.2922 0.0963 0.5258 0.068 Uiso 0.5 1 calc R U P C 1
H12B H 0.2705 0.1403 0.6126 0.068 Uiso 0.5 1 calc R U P C 1
H12C H 0.3718 0.1531 0.5754 0.068 Uiso 0.5 1 calc R U P C 1
C12B C 0.2569(8) 0.1623(7) 0.5594(7) 0.025(2) Uiso 0.5 1 d . . P C 2
H12D H 0.1967 0.1634 0.5279 0.038 Uiso 0.5 1 calc R U P C 2
H12E H 0.2455 0.1568 0.6180 0.038 Uiso 0.5 1 calc R U P C 2
H12F H 0.2942 0.1107 0.5419 0.038 Uiso 0.5 1 calc R U P C 2
C13 C 0.2738(4) 0.2437(4) 0.3741(5) 0.0364(14) Uani 1 1 d . . . . .
H13 H 0.3085 0.2714 0.3284 0.044 Uiso 1 1 calc R U . . .
C14 C 0.1791(5) 0.2909(5) 0.3770(7) 0.058(2) Uani 1 1 d . . . . .
H14A H 0.1370 0.2551 0.4101 0.086 Uiso 1 1 calc R U . . .
H14B H 0.1516 0.2972 0.3212 0.086 Uiso 1 1 calc R U . . .
H14C H 0.1878 0.3508 0.4017 0.086 Uiso 1 1 calc R U . . .
C15 C 0.2603(5) 0.1432(4) 0.3542(5) 0.0486(17) Uani 1 1 d . . . . .
H15A H 0.3217 0.1133 0.3546 0.073 Uiso 1 1 calc R U . . .
H15B H 0.2289 0.1368 0.2997 0.073 Uiso 1 1 calc R U . . .
H15C H 0.2216 0.1153 0.3955 0.073 Uiso 1 1 calc R U . . .
C16 C 0.5064(4) 0.4308(3) 0.2648(4) 0.0248(11) Uani 1 1 d . . . . .
H16A H 0.5353 0.4758 0.3031 0.030 Uiso 1 1 calc R U . . .
H16B H 0.5327 0.4410 0.2104 0.030 Uiso 1 1 calc R U . . .
C17 C 0.4010(4) 0.4483(3) 0.2575(4) 0.0267(12) Uani 1 1 d . . . . .
C18 C 0.3543(4) 0.4735(4) 0.3266(4) 0.0336(12) Uani 1 1 d . . . . .
H18 H 0.3873 0.4759 0.3785 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2589(5) 0.4953(4) 0.3202(5) 0.0417(15) Uani 1 1 d . . . . .
H19 H 0.2265 0.5122 0.3676 0.050 Uiso 1 1 calc R U . . .
C20 C 0.2121(4) 0.4922(4) 0.2444(5) 0.0419(16) Uani 1 1 d . . . . .
H20 H 0.1473 0.5076 0.2400 0.050 Uiso 1 1 calc R U . . .
C21 C 0.2569(5) 0.4673(4) 0.1755(5) 0.0416(16) Uani 1 1 d . . . . .
H21 H 0.2233 0.4656 0.1238 0.050 Uiso 1 1 calc R U . . .
C22 C 0.3537(4) 0.4440(4) 0.1813(4) 0.0333(13) Uani 1 1 d . . . . .
H22 H 0.3855 0.4258 0.1340 0.040 Uiso 1 1 calc R U . . .
C23 C 0.5004(3) 0.2337(3) 0.2294(4) 0.0242(11) Uani 1 1 d . . . . .
C24 C 0.5087(4) 0.2489(4) 0.1456(4) 0.0351(13) Uani 1 1 d . . . . .
H24 H 0.5283 0.3061 0.1261 0.042 Uiso 1 1 calc R U . . .
C25 C 0.4879(5) 0.1792(5) 0.0915(5) 0.0455(17) Uani 1 1 d . . . . .
H25 H 0.4930 0.1888 0.0342 0.055 Uiso 1 1 calc R U . . .
C26 C 0.4596(4) 0.0953(4) 0.1193(4) 0.0402(15) Uani 1 1 d . . . . .
H26 H 0.4466 0.0477 0.0814 0.048 Uiso 1 1 calc R U . . .
C27 C 0.4505(4) 0.0816(4) 0.2012(4) 0.0372(14) Uani 1 1 d . . . . .
H27 H 0.4297 0.0246 0.2200 0.045 Uiso 1 1 calc R U . . .
C28 C 0.4712(4) 0.1500(4) 0.2575(4) 0.0286(11) Uani 1 1 d . . . . .
H28 H 0.4655 0.1398 0.3146 0.034 Uiso 1 1 calc R U . . .
C29 C 0.6677(4) 0.3170(3) 0.3094(4) 0.0258(11) Uani 1 1 d . . . . .
C30 C 0.7138(4) 0.2349(4) 0.3032(4) 0.0279(12) Uani 1 1 d . . . . .
H30 H 0.6791 0.1816 0.2903 0.033 Uiso 1 1 calc R U . . .
C31 C 0.8107(4) 0.2308(4) 0.3158(5) 0.0358(14) Uani 1 1 d . . . . .
H31 H 0.8423 0.1746 0.3119 0.043 Uiso 1 1 calc R U . . .
C32 C 0.8615(4) 0.3085(4) 0.3341(5) 0.0378(14) Uani 1 1 d . . . . .
H32 H 0.9278 0.3053 0.3432 0.045 Uiso 1 1 calc R U . . .
C33 C 0.8165(4) 0.3903(4) 0.3393(5) 0.0412(15) Uani 1 1 d . . . . .
H33 H 0.8518 0.4435 0.3512 0.049 Uiso 1 1 calc R U . . .
C34 C 0.7186(4) 0.3953(4) 0.3269(5) 0.0404(15) Uani 1 1 d . . . . .
H34 H 0.6873 0.4518 0.3306 0.048 Uiso 1 1 calc R U . . .
B1 B 0.0442(4) 0.5284(4) 0.4393(5) 0.0310(14) Uani 1 1 d . . . . .
B2 B 0.5227(7) 0.5453(6) 0.4966(6) 0.053(2) 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
P1 C1 1.768(6) . ?
P1 C16 1.807(5) . ?
P1 C23 1.793(5) . ?
P1 C29 1.801(6) . ?
F1 B1 1.382(8) . ?
F2 B1 1.412(7) . ?
F3 B1 1.389(9) . ?
F4 B1 1.380(7) . ?
F5 B2 1.400(12) . ?
F6 B2 1.394(10) . ?
F7 B2 1.396(10) . ?
F8A B2 1.367(15) . ?
F8B B2 1.383(15) . ?
N1A C2 1.377(10) . ?
N1A C4A 1.479(16) . ?
N1A C7A 1.489(14) . ?
N1B C2 1.227(13) . ?
N1B C4B 1.54(2) . ?
N1B C7B 1.47(2) . ?
N2 C3 1.292(8) . ?
N2 C10A 1.495(15) . ?
N2 C10B 1.565(11) . ?
N2 C13 1.500(9) . ?
C1 C2 1.383(8) . ?
C1 C3 1.389(8) . ?
C2 C3 1.426(8) . ?
C4A C5A 1.519(16) . ?
C4A C6A 1.515(19) . ?
C4B C5B 1.55(3) . ?
C4B C6B 1.53(4) . ?
C7A C8A 1.542(14) . ?
C7A C9A 1.54(2) . ?
C7B C8B 1.49(2) . ?
C7B C9B 1.51(4) . ?
C10A C11A 1.54(3) . ?
C10A C12A 1.48(2) . ?
C10B C11B 1.49(2) . ?
C10B C12B 1.524(14) . ?
C13 C14 1.521(8) . ?
C13 C15 1.533(8) . ?
C16 C17 1.522(7) . ?
C17 C18 1.385(9) . ?
C17 C22 1.387(8) . ?
C18 C19 1.395(9) . ?
C19 C20 1.378(11) . ?
C20 C21 1.366(11) . ?
C21 C22 1.420(9) . ?
C23 C24 1.394(9) . ?
C23 C28 1.391(8) . ?
C24 C25 1.381(9) . ?
C25 C26 1.388(11) . ?
C26 C27 1.361(11) . ?
C27 C28 1.391(8) . ?
C29 C30 1.387(8) . ?
C29 C34 1.390(8) . ?
C30 C31 1.386(8) . ?
C31 C32 1.384(9) . ?
C32 C33 1.374(9) . ?
C33 C34 1.400(9) . ?

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
C1 P1 C16 110.8(3) . . ?
C1 P1 C23 108.5(3) . . ?
C1 P1 C29 108.8(3) . . ?
C23 P1 C16 111.5(2) . . ?
C23 P1 C29 109.5(2) . . ?
C29 P1 C16 107.7(2) . . ?
C2 N1A C4A 123.0(9) . . ?
C2 N1A C7A 120.3(9) . . ?
C4A N1A C7A 116.7(8) . . ?
C2 N1B C4B 106.7(12) . . ?
C2 N1B C7B 128.9(13) . . ?
C7B N1B C4B 124.1(12) . . ?
C3 N2 C10A 136.0(8) . . ?
C3 N2 C10B 109.4(6) . . ?
C3 N2 C13 118.2(5) . . ?
C10A N2 C13 105.5(7) . . ?
C13 N2 C10B 132.3(6) . . ?
C2 C1 P1 147.4(5) . . ?
C2 C1 C3 61.9(4) . . ?
C3 C1 P1 150.7(4) . . ?
N1A C2 C1 140.7(8) . . ?
N1A C2 C3 159.3(7) . . ?
N1B C2 C1 161.3(9) . . ?
N1B C2 C3 138.8(10) . . ?
C1 C2 C3 59.2(4) . . ?
N2 C3 C1 149.7(6) . . ?
N2 C3 C2 151.5(6) . . ?
C1 C3 C2 58.8(4) . . ?
N1A C4A C5A 112.7(11) . . ?
N1A C4A C6A 113.1(10) . . ?
C6A C4A C5A 111.3(10) . . ?
N1B C4B C5B 116.8(19) . . ?
C6B C4B N1B 111.5(15) . . ?
C6B C4B C5B 109.7(18) . . ?
N1A C7A C8A 112.8(8) . . ?
N1A C7A C9A 112.3(9) . . ?
C9A C7A C8A 115.3(10) . . ?
N1B C7B C8B 113.6(14) . . ?
N1B C7B C9B 112.9(16) . . ?
C8B C7B C9B 112.1(17) . . ?
N2 C10A C11A 107.8(13) . . ?
C12A C10A N2 110.2(11) . . ?
C12A C10A C11A 116.6(14) . . ?
C11B C10B N2 110.1(9) . . ?
C11B C10B C12B 114.9(10) . . ?
C12B C10B N2 109.0(8) . . ?
N2 C13 C14 113.1(6) . . ?
N2 C13 C15 110.3(5) . . ?
C14 C13 C15 110.5(5) . . ?
C17 C16 P1 115.8(4) . . ?
C18 C17 C16 119.3(5) . . ?
C18 C17 C22 120.6(5) . . ?
C22 C17 C16 120.0(5) . . ?
C17 C18 C19 120.1(6) . . ?
C20 C19 C18 119.3(7) . . ?
C21 C20 C19 121.4(6) . . ?
C20 C21 C22 119.8(6) . . ?
C17 C22 C21 118.7(6) . . ?
C24 C23 P1 118.4(4) . . ?
C28 C23 P1 120.8(5) . . ?
C28 C23 C24 120.5(5) . . ?
C25 C24 C23 118.7(6) . . ?
C24 C25 C26 121.1(7) . . ?
C27 C26 C25 119.7(6) . . ?
C26 C27 C28 120.8(6) . . ?
C27 C28 C23 119.2(6) . . ?
C30 C29 P1 119.1(4) . . ?
C30 C29 C34 120.1(5) . . ?
C34 C29 P1 120.8(4) . . ?
C31 C30 C29 119.9(5) . . ?
C32 C31 C30 120.1(5) . . ?
C33 C32 C31 120.3(6) . . ?
C32 C33 C34 120.1(5) . . ?
C29 C34 C33 119.5(5) . . ?
F1 B1 F2 107.5(5) . . ?
F1 B1 F3 109.5(5) . . ?
F3 B1 F2 107.7(6) . . ?
F4 B1 F1 112.8(6) . . ?
F4 B1 F2 107.8(5) . . ?
F4 B1 F3 111.2(5) . . ?
F6 B2 F5 106.2(6) . . ?
F6 B2 F7 109.9(7) . . ?
F7 B2 F5 106.5(8) . . ?
F8A B2 F5 121.7(9) . . ?
F8A B2 F6 103.0(9) . . ?
F8A B2 F7 109.0(8) . . ?
F8B B2 F5 100.5(9) . . ?
F8B B2 F6 119.8(9) . . ?
F8B B2 F7 112.4(8) . . ?


_shelxl_version_number           2013-3


####################################################################### 
# 
# 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_9051sadabs
_database_code_depnum_ccdc_archive 'CCDC 1564414'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT03197A 2017
_audit_update_record             
;
2017-07-25 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_block_code                GAA-GA-246-02


_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'p 21'
_symmetry_space_group_name_Hall  'p 2yb'
_symmetry_Int_Tables_number      4


_audit_creation_date             2014-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_systematic        
;
 Title
;
_chemical_compound_source        dichloromethane,acetonitrile
_chemical_formula_moiety         'C33 H40 F3 N2 P, C H2 Cl2, 2(B F4)'
_chemical_formula_sum            'C34 H42 B2 Cl2 F11 N2 P'
_chemical_formula_weight         811.18
_chemical_absolute_configuration rmad

_chemical_melting_point          ?
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'
B B 0.0013 0.0007 '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'
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'

_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_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.6966(4)
_cell_length_b                   10.6522(9)
_cell_length_c                   16.6805(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.699(4)
_cell_angle_gamma                90
_cell_volume                     1896.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    51247


_cell_measurement_temperature    100
_cell_measurement_theta_max      35.9998
_cell_measurement_theta_min      2.6986
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.98277
_exptl_absorpt_correction_T_min  0.97101

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.0600
0.00 -1.00 0.00 0.0700
0.00 0.00 1.00 0.0700
0.00 0.00 -1.00 0.1000
-1.00 0.00 0.00 0.1450
1.00 0.00 0.00 0.1450
-1.00 0.00 -1.00 0.1300
1.00 0.00 -1.00 0.1300
-1.00 -2.00 0.00 0.0800
-1.00 2.00 0.00 0.0850
1.00 -1.00 0.00 0.1250

_exptl_crystal_description       prism
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            48825
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         36.027
_diffrn_reflns_theta_min         2.701

_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                16837
_reflns_number_total             17618
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'REVALCCD V. 1.6, 2008'

_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'REVALCCD V. 1.6, 2008'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_refine_diff_density_max         1.181
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 7596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         17618
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)²+0.4828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0998

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.8959 and 1.0000 (SADABS).

Highest peak        ?
Deepest hole        ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H34C)=Sof(H34D)=Sof(Cl1B)=Sof(Cl2B)=1-FVAR(1)
 Sof(H34B)=Sof(H34A)=Sof(Cl1A)=Sof(Cl2A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C34(H34B,H34A), C34(H34C,H34D)
3.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26),
 C27(H27), C29(H29), C30(H30), C32(H32), C33(H33)
3.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,
 H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.20070(11) 0.42192(12) 0.74440(7) 0.01288(18) Uani 1 1 d . . . . .
C2 C 0.09042(11) 0.48026(12) 0.71572(7) 0.01240(18) Uani 1 1 d . . . . .
C3 C 0.14398(11) 0.50687(12) 0.79434(7) 0.01253(18) Uani 1 1 d . . . . .
C4 C 0.00672(13) 0.42274(14) 0.58239(8) 0.0167(2) Uani 1 1 d . . . . .
H4 H -0.0719 0.4428 0.5491 0.020 Uiso 1 1 calc R . . . .
C5 C 0.11636(15) 0.46486(16) 0.53504(9) 0.0212(2) Uani 1 1 d . . . . .
H5A H 0.1134 0.5562 0.5282 0.032 Uiso 1 1 calc GR . . . .
H5B H 0.1109 0.4243 0.4822 0.032 Uiso 1 1 calc GR . . . .
H5C H 0.1953 0.4412 0.5643 0.032 Uiso 1 1 calc GR . . . .
C6 C 0.00561(17) 0.28192(16) 0.59946(11) 0.0249(3) Uani 1 1 d . . . . .
H6A H 0.0846 0.2577 0.6284 0.037 Uiso 1 1 calc GR . . . .
H6B H -0.0041 0.2357 0.5486 0.037 Uiso 1 1 calc GR . . . .
H6C H -0.0644 0.2619 0.6323 0.037 Uiso 1 1 calc GR . . . .
C7 C -0.10802(13) 0.57461(14) 0.67130(8) 0.0173(2) Uani 1 1 d . . . . .
H7 H -0.0951 0.6144 0.7255 0.021 Uiso 1 1 calc R . . . .
C8 C -0.11750(15) 0.67940(16) 0.60923(11) 0.0232(3) Uani 1 1 d . . . . .
H8A H -0.0396 0.7280 0.6123 0.035 Uiso 1 1 calc GR . . . .
H8B H -0.1878 0.7346 0.6200 0.035 Uiso 1 1 calc GR . . . .
H8C H -0.1313 0.6431 0.5554 0.035 Uiso 1 1 calc GR . . . .
C9 C -0.22604(14) 0.49402(18) 0.67148(10) 0.0227(3) Uani 1 1 d . . . . .
H9A H -0.2415 0.4541 0.6188 0.034 Uiso 1 1 calc GR . . . .
H9B H -0.2977 0.5470 0.6828 0.034 Uiso 1 1 calc GR . . . .
H9C H -0.2147 0.4291 0.7130 0.034 Uiso 1 1 calc GR . . . .
C10 C 0.06981(13) 0.66664(13) 0.88773(8) 0.0162(2) Uani 1 1 d . . . . .
H10 H 0.1042 0.6961 0.9416 0.019 Uiso 1 1 calc R . . . .
C11 C 0.08168(16) 0.77615(15) 0.83015(11) 0.0227(3) Uani 1 1 d . . . . .
H11A H 0.1701 0.7991 0.8281 0.034 Uiso 1 1 calc GR . . . .
H11B H 0.0346 0.8482 0.8489 0.034 Uiso 1 1 calc GR . . . .
H11C H 0.0479 0.7517 0.7764 0.034 Uiso 1 1 calc GR . . . .
C12 C -0.06424(14) 0.62541(16) 0.89783(9) 0.0214(3) Uani 1 1 d . . . . .
H12A H -0.1021 0.5962 0.8461 0.032 Uiso 1 1 calc GR . . . .
H12B H -0.1125 0.6964 0.9168 0.032 Uiso 1 1 calc GR . . . .
H12C H -0.0646 0.5570 0.9371 0.032 Uiso 1 1 calc GR . . . .
C13 C 0.24307(13) 0.50855(13) 0.92695(8) 0.0155(2) Uani 1 1 d . . . . .
H13 H 0.2943 0.4442 0.9003 0.019 Uiso 1 1 calc R . . . .
C14 C 0.17450(16) 0.44178(16) 0.99198(9) 0.0225(3) Uani 1 1 d . . . . .
H14A H 0.1229 0.5024 1.0192 0.034 Uiso 1 1 calc GR . . . .
H14B H 0.2357 0.4041 1.0311 0.034 Uiso 1 1 calc GR . . . .
H14C H 0.1208 0.3759 0.9674 0.034 Uiso 1 1 calc GR . . . .
C15 C 0.33263(14) 0.60930(16) 0.96100(9) 0.0209(2) Uani 1 1 d . . . . .
H15A H 0.3643 0.6581 0.9168 0.031 Uiso 1 1 calc GR . . . .
H15B H 0.4030 0.5695 0.9918 0.031 Uiso 1 1 calc GR . . . .
H15C H 0.2882 0.6651 0.9962 0.031 Uiso 1 1 calc GR . . . .
C16 C 0.35289(12) 0.21258(12) 0.80179(8) 0.01339(19) Uani 1 1 d . . . . .
C17 C 0.25095(13) 0.17919(14) 0.84582(9) 0.0173(2) Uani 1 1 d . . . . .
H17 H 0.1767 0.2283 0.8422 0.021 Uiso 1 1 calc R . . . .
C18 C 0.25897(16) 0.07363(15) 0.89499(10) 0.0221(3) Uani 1 1 d . . . . .
H18 H 0.1910 0.0494 0.9256 0.027 Uiso 1 1 calc R . . . .
C19 C 0.36922(17) 0.00497(14) 0.89795(9) 0.0220(3) Uani 1 1 d . . . . .
C20 C 0.47074(15) 0.03434(14) 0.85404(9) 0.0193(2) Uani 1 1 d . . . . .
H20 H 0.5441 -0.0161 0.8575 0.023 Uiso 1 1 calc R . . . .
C21 C 0.46237(13) 0.13935(13) 0.80496(8) 0.0158(2) Uani 1 1 d . . . . .
H21 H 0.5301 0.1617 0.7737 0.019 Uiso 1 1 calc R . . . .
C22 C 0.45403(11) 0.46668(12) 0.77551(7) 0.01240(18) Uani 1 1 d . . . . .
C23 C 0.54991(12) 0.44071(12) 0.83442(8) 0.01430(19) Uani 1 1 d . . . . .
H23 H 0.5657 0.3568 0.8514 0.017 Uiso 1 1 calc R . . . .
C24 C 0.62172(13) 0.53862(14) 0.86780(9) 0.0168(2) Uani 1 1 d . . . . .
H24 H 0.6869 0.5231 0.9080 0.020 Uiso 1 1 calc R . . . .
C25 C 0.59563(13) 0.65919(13) 0.84091(9) 0.0174(2) Uani 1 1 d . . . . .
C26 C 0.50504(13) 0.68785(13) 0.78041(9) 0.0166(2) Uani 1 1 d . . . . .
H26 H 0.4931 0.7715 0.7617 0.020 Uiso 1 1 calc R . . . .
C27 C 0.43263(12) 0.59011(12) 0.74816(8) 0.01386(19) Uani 1 1 d . . . . .
H27 H 0.3684 0.6065 0.7075 0.017 Uiso 1 1 calc R . . . .
C28 C 0.38023(12) 0.29859(12) 0.64004(8) 0.01293(18) Uani 1 1 d . . . . .
C29 C 0.44654(14) 0.37656(14) 0.59001(9) 0.0177(2) Uani 1 1 d . . . . .
H29 H 0.4738 0.4572 0.6082 0.021 Uiso 1 1 calc R . . . .
C30 C 0.47232(14) 0.33542(16) 0.51363(9) 0.0209(2) Uani 1 1 d . . . . .
H30 H 0.5167 0.3870 0.4787 0.025 Uiso 1 1 calc R . . . .
C31 C 0.43127(13) 0.21731(15) 0.49028(9) 0.0186(2) Uani 1 1 d . . . . .
C32 C 0.36628(14) 0.13778(13) 0.53834(9) 0.0175(2) Uani 1 1 d . . . . .
H32 H 0.3400 0.0571 0.5197 0.021 Uiso 1 1 calc R . . . .
C33 C 0.34050(13) 0.17891(12) 0.61440(8) 0.0152(2) Uani 1 1 d . . . . .
H33 H 0.2963 0.1264 0.6489 0.018 Uiso 1 1 calc R . . . .
F1 F 0.37885(14) -0.09646(11) 0.94632(8) 0.0345(3) Uani 1 1 d . . . . .
F2 F 0.66000(10) 0.75497(10) 0.87700(7) 0.0258(2) Uani 1 1 d . . . . .
F3 F 0.45683(11) 0.17690(12) 0.41635(6) 0.0273(2) Uani 1 1 d . . . . .
N1 N 0.00290(10) 0.49445(11) 0.65899(7) 0.01385(17) Uani 1 1 d . . . . .
N2 N 0.15066(11) 0.56011(11) 0.86444(7) 0.01377(17) Uani 1 1 d . . . . .
P1 P 0.34729(3) 0.34753(3) 0.73864(2) 0.01096(5) Uani 1 1 d . . . . .
C34 C 0.1806(2) 0.5370(2) 0.30568(13) 0.0326(4) Uani 1 1 d . . . . .
H34B H 0.1488 0.6089 0.2727 0.039 Uiso 0.626(7) 1 calc R . P A 1
H34A H 0.1109 0.5057 0.3365 0.039 Uiso 0.626(7) 1 calc R . P A 1
H34C H 0.1120 0.5050 0.3372 0.039 Uiso 0.374(7) 1 calc R . P A 2
H34D H 0.1441 0.5960 0.2647 0.039 Uiso 0.374(7) 1 calc R . P A 2
Cl1A Cl 0.22916(13) 0.41455(8) 0.24028(10) 0.0305(3) Uiso 0.626(7) 1 d . . P A
1
Cl1B Cl 0.2521(3) 0.41302(18) 0.2590(2) 0.0403(5) Uiso 0.374(7) 1 d . . P A 2
Cl2A Cl 0.29974(11) 0.5877(2) 0.37158(7) 0.0375(3) Uiso 0.626(7) 1 d . . P A 1
Cl2B Cl 0.29807(17) 0.6196(3) 0.37293(11) 0.0364(5) Uiso 0.374(7) 1 d . . P A 2
B2 B 0.11987(17) 0.76426(17) 0.12563(11) 0.0214(3) Uani 1 1 d . . . . .
F8 F 0.05928(12) 0.83800(13) 0.18105(7) 0.0326(2) Uani 1 1 d . . . . .
F9 F 0.23118(12) 0.71787(15) 0.16122(9) 0.0383(3) Uani 1 1 d . . . . .
F10 F 0.14731(13) 0.83637(13) 0.05939(7) 0.0331(2) Uani 1 1 d . . . . .
F11 F 0.03986(13) 0.66746(15) 0.10091(10) 0.0438(4) Uani 1 1 d . . . . .
B1 B 0.77971(17) 0.34886(19) 0.37430(12) 0.0236(3) Uani 1 1 d . . . . .
F4 F 0.75787(14) 0.35747(16) 0.45567(8) 0.0400(3) Uani 1 1 d . . . . .
F5 F 0.88279(16) 0.42227(15) 0.36036(12) 0.0491(4) Uani 1 1 d . . . . .
F6 F 0.80324(11) 0.22399(11) 0.35449(8) 0.0281(2) Uani 1 1 d . . . . .
F7 F 0.67400(16) 0.39031(14) 0.32948(11) 0.0532(5) 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 1.3906(17) . y
C1 C3 1.3950(18) . y
C1 P1 1.7650(12) . y
C2 C3 1.4253(17) . y
C2 N1 1.2964(15) . y
C3 N2 1.2974(16) . y
C4 H4 1.0000 . n
C4 C5 1.523(2) . y
C4 C6 1.527(2) . y
C4 N1 1.4914(18) . y
C5 H5A 0.9800 . n
C5 H5B 0.9800 . n
C5 H5C 0.9800 . n
C6 H6A 0.9800 . n
C6 H6B 0.9800 . n
C6 H6C 0.9800 . n
C7 H7 1.0000 . n
C7 C8 1.521(2) . y
C7 C9 1.527(2) . y
C7 N1 1.4867(18) . y
C8 H8A 0.9800 . n
C8 H8B 0.9800 . n
C8 H8C 0.9800 . n
C9 H9A 0.9800 . n
C9 H9B 0.9800 . n
C9 H9C 0.9800 . n
C10 H10 1.0000 . n
C10 C11 1.521(2) . y
C10 C12 1.519(2) . y
C10 N2 1.4933(17) . y
C11 H11A 0.9800 . n
C11 H11B 0.9800 . n
C11 H11C 0.9800 . n
C12 H12A 0.9800 . n
C12 H12B 0.9800 . n
C12 H12C 0.9800 . n
C13 H13 1.0000 . n
C13 C14 1.524(2) . y
C13 C15 1.524(2) . y
C13 N2 1.4944(17) . y
C14 H14A 0.9800 . n
C14 H14B 0.9800 . n
C14 H14C 0.9800 . n
C15 H15A 0.9800 . n
C15 H15B 0.9800 . n
C15 H15C 0.9800 . n
C16 C17 1.3994(19) . y
C16 C21 1.4052(18) . y
C16 P1 1.7808(13) . y
C17 H17 0.9500 . n
C17 C18 1.391(2) . y
C18 H18 0.9500 . n
C18 C19 1.386(2) . y
C19 C20 1.384(2) . y
C19 F1 1.3484(18) . y
C20 H20 0.9500 . n
C20 C21 1.386(2) . y
C21 H21 0.9500 . n
C22 C23 1.4013(17) . y
C22 C27 1.4056(18) . y
C22 P1 1.7894(12) . y
C23 H23 0.9500 . n
C23 C24 1.3902(19) . y
C24 H24 0.9500 . n
C24 C25 1.383(2) . y
C25 C26 1.3874(19) . y
C25 F2 1.3505(16) . y
C26 H26 0.9500 . n
C26 C27 1.3854(18) . y
C27 H27 0.9500 . n
C28 C29 1.4020(19) . y
C28 C33 1.4019(18) . y
C28 P1 1.7821(13) . y
C29 H29 0.9500 . n
C29 C30 1.392(2) . y
C30 H30 0.9500 . n
C30 C31 1.380(2) . y
C31 C32 1.384(2) . y
C31 F3 1.3506(17) . y
C32 H32 0.9500 . n
C32 C33 1.3865(19) . y
C33 H33 0.9500 . n
C34 H34B 0.9900 . n
C34 H34A 0.9900 . n
C34 H34C 0.9900 . n
C34 H34D 0.9900 . n
C34 Cl1A 1.799(2) . y
C34 Cl1B 1.736(3) . y
C34 Cl2A 1.716(3) . y
C34 Cl2B 1.852(3) . y
B2 F8 1.403(2) . y
B2 F9 1.387(2) . y
B2 F10 1.392(2) . y
B2 F11 1.386(2) . y
B1 F4 1.395(2) . y
B1 F5 1.384(2) . y
B1 F6 1.397(2) . y
B1 F7 1.387(2) . y

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 C3 61.55(9) . . y
C2 C1 P1 156.75(10) . . y
C3 C1 P1 138.23(10) . . y
C1 C2 C3 59.38(9) . . y
N1 C2 C1 149.30(13) . . y
N1 C2 C3 151.28(12) . . y
C1 C3 C2 59.07(9) . . y
N2 C3 C1 145.18(12) . . y
N2 C3 C2 155.74(12) . . y
C5 C4 H4 107.3 . . n
C5 C4 C6 113.67(13) . . y
C6 C4 H4 107.3 . . n
N1 C4 H4 107.3 . . n
N1 C4 C5 110.97(12) . . y
N1 C4 C6 110.03(12) . . y
C4 C5 H5A 109.5 . . n
C4 C5 H5B 109.5 . . n
C4 C5 H5C 109.5 . . n
H5A C5 H5B 109.5 . . n
H5A C5 H5C 109.5 . . n
H5B C5 H5C 109.5 . . n
C4 C6 H6A 109.5 . . n
C4 C6 H6B 109.5 . . n
C4 C6 H6C 109.5 . . n
H6A C6 H6B 109.5 . . n
H6A C6 H6C 109.5 . . n
H6B C6 H6C 109.5 . . n
C8 C7 H7 107.6 . . n
C8 C7 C9 113.27(12) . . y
C9 C7 H7 107.6 . . n
N1 C7 H7 107.6 . . n
N1 C7 C8 110.25(12) . . y
N1 C7 C9 110.16(13) . . y
C7 C8 H8A 109.5 . . n
C7 C8 H8B 109.5 . . n
C7 C8 H8C 109.5 . . n
H8A C8 H8B 109.5 . . n
H8A C8 H8C 109.5 . . n
H8B C8 H8C 109.5 . . n
C7 C9 H9A 109.5 . . n
C7 C9 H9B 109.5 . . n
C7 C9 H9C 109.5 . . n
H9A C9 H9B 109.5 . . n
H9A C9 H9C 109.5 . . n
H9B C9 H9C 109.5 . . n
C11 C10 H10 106.6 . . n
C12 C10 H10 106.6 . . n
C12 C10 C11 114.17(12) . . y
N2 C10 H10 106.6 . . n
N2 C10 C11 110.19(12) . . y
N2 C10 C12 112.06(12) . . y
C10 C11 H11A 109.5 . . n
C10 C11 H11B 109.5 . . n
C10 C11 H11C 109.5 . . n
H11A C11 H11B 109.5 . . n
H11A C11 H11C 109.5 . . n
H11B C11 H11C 109.5 . . n
C10 C12 H12A 109.5 . . n
C10 C12 H12B 109.5 . . n
C10 C12 H12C 109.5 . . n
H12A C12 H12B 109.5 . . n
H12A C12 H12C 109.5 . . n
H12B C12 H12C 109.5 . . n
C14 C13 H13 107.4 . . n
C15 C13 H13 107.4 . . n
C15 C13 C14 112.54(12) . . y
N2 C13 H13 107.4 . . n
N2 C13 C14 109.94(12) . . y
N2 C13 C15 111.89(12) . . y
C13 C14 H14A 109.5 . . n
C13 C14 H14B 109.5 . . n
C13 C14 H14C 109.5 . . n
H14A C14 H14B 109.5 . . n
H14A C14 H14C 109.5 . . n
H14B C14 H14C 109.5 . . n
C13 C15 H15A 109.5 . . n
C13 C15 H15B 109.5 . . n
C13 C15 H15C 109.5 . . n
H15A C15 H15B 109.5 . . n
H15A C15 H15C 109.5 . . n
H15B C15 H15C 109.5 . . n
C17 C16 C21 120.99(12) . . y
C17 C16 P1 121.20(10) . . y
C21 C16 P1 117.81(10) . . y
C16 C17 H17 120.2 . . n
C18 C17 C16 119.62(14) . . y
C18 C17 H17 120.2 . . n
C17 C18 H18 121.1 . . n
C19 C18 C17 117.88(14) . . y
C19 C18 H18 121.1 . . n
C20 C19 C18 123.82(14) . . y
F1 C19 C18 118.44(15) . . y
F1 C19 C20 117.74(15) . . y
C19 C20 H20 120.9 . . n
C19 C20 C21 118.17(14) . . y
C21 C20 H20 120.9 . . n
C16 C21 H21 120.3 . . n
C20 C21 C16 119.49(13) . . y
C20 C21 H21 120.3 . . n
C23 C22 C27 120.58(11) . . y
C23 C22 P1 121.52(10) . . y
C27 C22 P1 117.71(9) . . y
C22 C23 H23 120.2 . . n
C24 C23 C22 119.55(12) . . y
C24 C23 H23 120.2 . . n
C23 C24 H24 120.9 . . n
C25 C24 C23 118.17(12) . . y
C25 C24 H24 120.9 . . n
C24 C25 C26 123.86(12) . . y
F2 C25 C24 118.08(12) . . y
F2 C25 C26 118.04(13) . . y
C25 C26 H26 121.2 . . n
C27 C26 C25 117.63(12) . . y
C27 C26 H26 121.2 . . n
C22 C27 H27 119.9 . . n
C26 C27 C22 120.11(12) . . y
C26 C27 H27 119.9 . . n
C29 C28 P1 120.92(10) . . y
C33 C28 C29 120.81(12) . . y
C33 C28 P1 118.26(10) . . y
C28 C29 H29 120.1 . . n
C30 C29 C28 119.75(13) . . y
C30 C29 H29 120.1 . . n
C29 C30 H30 121.1 . . n
C31 C30 C29 117.85(13) . . y
C31 C30 H30 121.1 . . n
C30 C31 C32 123.84(13) . . y
F3 C31 C30 117.95(14) . . y
F3 C31 C32 118.21(13) . . y
C31 C32 H32 120.9 . . n
C31 C32 C33 118.27(13) . . y
C33 C32 H32 120.9 . . n
C28 C33 H33 120.3 . . n
C32 C33 C28 119.49(13) . . y
C32 C33 H33 120.3 . . n
C2 N1 C4 120.48(11) . . y
C2 N1 C7 120.75(11) . . y
C7 N1 C4 118.60(10) . . y
C3 N2 C10 124.58(11) . . y
C3 N2 C13 117.62(11) . . y
C10 N2 C13 117.77(10) . . y
C1 P1 C16 109.04(6) . . y
C1 P1 C22 102.26(6) . . y
C1 P1 C28 114.26(6) . . y
C16 P1 C22 111.90(6) . . y
C16 P1 C28 107.98(6) . . y
C28 P1 C22 111.40(6) . . y
H34B C34 H34A 107.8 . . n
H34C C34 H34D 108.3 . . n
Cl1A C34 H34B 109.1 . . n
Cl1A C34 H34A 109.1 . . n
Cl1B C34 H34C 109.8 . . n
Cl1B C34 H34D 109.8 . . n
Cl1B C34 Cl2B 109.34(15) . . y
Cl2A C34 H34B 109.1 . . n
Cl2A C34 H34A 109.1 . . n
Cl2A C34 Cl1A 112.65(12) . . y
Cl2B C34 H34C 109.8 . . n
Cl2B C34 H34D 109.8 . . n
F9 B2 F8 109.74(15) . . y
F9 B2 F10 108.49(15) . . y
F10 B2 F8 110.11(15) . . y
F11 B2 F8 108.05(14) . . y
F11 B2 F9 111.04(16) . . y
F11 B2 F10 109.40(16) . . y
F4 B1 F6 109.68(17) . . y
F5 B1 F4 108.16(16) . . y
F5 B1 F6 109.91(15) . . y
F5 B1 F7 111.12(19) . . y
F7 B1 F4 108.77(16) . . y
F7 B1 F6 109.18(14) . . y

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
C1 C2 C3 N2 -178.9(3) . . . . n
C1 C2 N1 C4 -1.2(3) . . . . n
C1 C2 N1 C7 174.0(2) . . . . n
C1 C3 N2 C10 170.63(18) . . . . n
C1 C3 N2 C13 -11.3(3) . . . . n
C2 C1 C3 N2 179.2(2) . . . . n
C2 C1 P1 C16 -134.1(3) . . . . n
C2 C1 P1 C22 107.3(3) . . . . n
C2 C1 P1 C28 -13.2(3) . . . . n
C2 C3 N2 C10 -11.0(4) . . . . n
C2 C3 N2 C13 167.0(3) . . . . n
C3 C1 C2 N1 -177.8(3) . . . . n
C3 C1 P1 C16 83.29(16) . . . . n
C3 C1 P1 C22 -35.31(16) . . . . n
C3 C1 P1 C28 -155.80(14) . . . . n
C3 C2 N1 C4 -177.2(2) . . . . n
C3 C2 N1 C7 -2.0(3) . . . . n
C5 C4 N1 C2 -67.15(17) . . . . n
C5 C4 N1 C7 117.55(14) . . . . n
C6 C4 N1 C2 59.53(17) . . . . n
C6 C4 N1 C7 -115.77(14) . . . . n
C8 C7 N1 C2 121.28(14) . . . . n
C8 C7 N1 C4 -63.43(16) . . . . n
C9 C7 N1 C2 -112.98(14) . . . . n
C9 C7 N1 C4 62.31(16) . . . . n
C11 C10 N2 C3 -56.40(18) . . . . n
C11 C10 N2 C13 125.57(13) . . . . n
C12 C10 N2 C3 71.90(17) . . . . n
C12 C10 N2 C13 -106.13(14) . . . . n
C14 C13 N2 C3 -109.51(14) . . . . n
C14 C13 N2 C10 68.65(16) . . . . n
C15 C13 N2 C3 124.67(13) . . . . n
C15 C13 N2 C10 -57.16(16) . . . . n
C16 C17 C18 C19 -0.2(2) . . . . n
C17 C16 C21 C20 -1.7(2) . . . . n
C17 C16 P1 C1 0.48(13) . . . . n
C17 C16 P1 C22 112.86(11) . . . . n
C17 C16 P1 C28 -124.20(11) . . . . n
C17 C18 C19 C20 -1.0(2) . . . . n
C17 C18 C19 F1 179.02(14) . . . . n
C18 C19 C20 C21 0.8(2) . . . . n
C19 C20 C21 C16 0.5(2) . . . . n
C21 C16 C17 C18 1.5(2) . . . . n
C21 C16 P1 C1 179.42(10) . . . . n
C21 C16 P1 C22 -68.20(12) . . . . n
C21 C16 P1 C28 54.75(12) . . . . n
C22 C23 C24 C25 -0.3(2) . . . . n
C23 C22 C27 C26 -1.2(2) . . . . n
C23 C22 P1 C1 131.50(11) . . . . n
C23 C22 P1 C16 14.94(13) . . . . n
C23 C22 P1 C28 -106.04(11) . . . . n
C23 C24 C25 C26 -2.5(2) . . . . n
C23 C24 C25 F2 175.82(13) . . . . n
C24 C25 C26 C27 3.4(2) . . . . n
C25 C26 C27 C22 -1.5(2) . . . . n
C27 C22 C23 C24 2.0(2) . . . . n
C27 C22 P1 C1 -43.49(12) . . . . n
C27 C22 P1 C16 -160.05(10) . . . . n
C27 C22 P1 C28 78.96(11) . . . . n
C28 C29 C30 C31 -0.3(2) . . . . n
C29 C28 C33 C32 -0.6(2) . . . . n
C29 C28 P1 C1 92.98(12) . . . . n
C29 C28 P1 C16 -145.52(11) . . . . n
C29 C28 P1 C22 -22.27(13) . . . . n
C29 C30 C31 C32 0.0(2) . . . . n
C29 C30 C31 F3 -179.62(14) . . . . n
C30 C31 C32 C33 0.1(2) . . . . n
C31 C32 C33 C28 0.2(2) . . . . n
C33 C28 C29 C30 0.6(2) . . . . n
C33 C28 P1 C1 -88.39(11) . . . . n
C33 C28 P1 C16 33.11(12) . . . . n
C33 C28 P1 C22 156.36(10) . . . . n
F1 C19 C20 C21 -179.18(14) . . . . n
F2 C25 C26 C27 -174.95(13) . . . . n
F3 C31 C32 C33 179.70(13) . . . . n
N1 C2 C3 C1 177.6(3) . . . . n
N1 C2 C3 N2 -1.3(5) . . . . n
P1 C1 C2 C3 -152.6(3) . . . . n
P1 C1 C2 N1 29.6(4) . . . . n
P1 C1 C3 C2 164.16(17) . . . . n
P1 C1 C3 N2 -16.6(3) . . . . n
P1 C16 C17 C18 -179.54(11) . . . . n
P1 C16 C21 C20 179.35(11) . . . . n
P1 C22 C23 C24 -172.81(11) . . . . n
P1 C22 C27 C26 173.89(11) . . . . n
P1 C28 C29 C30 179.23(12) . . . . n
P1 C28 C33 C32 -179.18(10) . . . . n

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'


_diffrn_radiation_monochromator  'Incoatec Helios focusing multilayer optics'
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;

####################################################################### 
# 
# 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_8890
_database_code_depnum_ccdc_archive 'CCDC 1564418'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT03197A 2017
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_date             2014-07-21
_audit_block_code                GAA-GA-170-01
_chemical_compound_source        dichloromethane

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0300
0.00 0.00 1.00 0.0300
-2.00 0.00 1.00 0.0700
2.00 0.00 -1.00 0.0700
1.00 -2.00 -1.00 0.1350
-2.00 1.00 1.00 0.1200
1.00 2.00 0.00 0.2000
_diffrn_radiation_monochromator  'MONTEL graded multilayer optic'
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?

_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H31 N2 P, 2(B F4), C H2 Cl2'
_chemical_formula_sum            'C30 H33 B2 Cl2 F8 N2 P'
_chemical_formula_weight         697.07

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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 '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'
Cl Cl 0.3639 0.7018 '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                   19.130(5)
_cell_length_b                   8.863(2)
_cell_length_c                   20.028(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.084(6)
_cell_angle_gamma                90
_cell_volume                     3245.8(15)
_cell_formula_units_Z            4


_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      4.5768
_cell_measurement_theta_max      67.4161

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    2.895
_shelx_estimated_absorpt_T_min   0.353
_shelx_estimated_absorpt_T_max   0.832

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.72198
_exptl_absorpt_correction_T_max  0.92210
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           Cu-K\a
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_detector_area_resol_mean 66.67
_diffrn_reflns_number            62738
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.416
_diffrn_reflns_theta_max         67.137
_diffrn_reflns_theta_full        67.137
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5738
_reflns_number_gt                4563
_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       'APEX2 (Bruker AXS, 2005-2013)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2012)'
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.6246 and 0.9794 (SADABS).

INTENSITY STATISTICS FOR DATASET 

 Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma

  Inf - 3.63      95     95    100.0     5.83     57.96   38.82  0.0266  0.0167
 3.63 - 2.37     214    214    100.0    11.13     38.74   47.40  0.0348  0.0143
 2.37 - 1.86     306    306    100.0    14.47     20.24   49.15  0.0346  0.0134
 1.86 - 1.61     316    316    100.0    13.45     16.79   42.78  0.0327  0.0153
 1.61 - 1.45     318    318    100.0    12.47     11.40   32.11  0.0415  0.0197
 1.45 - 1.35     297    297    100.0    17.66     10.39   31.87  0.0681  0.0201
 1.35 - 1.26     326    326    100.0    17.79      7.49   25.74  0.0861  0.0250
 1.26 - 1.20     307    307    100.0    16.84      9.79   27.80  0.0856  0.0238
 1.20 - 1.15     283    283    100.0    14.29      7.12   20.51  0.1034  0.0334
 1.15 - 1.10     332    332    100.0    12.97      5.86   16.98  0.1114  0.0405
 1.10 - 1.06     331    331    100.0    12.36      4.86   15.01  0.1313  0.0475
 1.06 - 1.03     273    273    100.0    11.79      4.95   14.44  0.1404  0.0488
 1.03 - 1.00     288    288    100.0    11.41      4.13   12.64  0.1638  0.0565
 1.00 - 0.97     350    350    100.0    10.68      3.60   11.50  0.1858  0.0639
 0.97 - 0.94     401    401    100.0     8.11      3.02    8.13  0.1989  0.0919
 0.94 - 0.92     276    276    100.0     5.67      2.75    5.90  0.2035  0.1290
 0.92 - 0.90     312    312    100.0     5.22      2.65    5.78  0.2216  0.1324
 0.90 - 0.88     330    330    100.0     4.93      1.90    4.70  0.2581  0.1685
 0.88 - 0.87     189    189    100.0     4.65      1.63    4.31  0.2953  0.1861
 0.87 - 0.85     407    410     99.3     4.17      1.40    3.60  0.2908  0.2236
 0.85 - 0.84     199    261     76.2     1.93      1.27    2.53  0.2800  0.3403
#-------------------------------------------------------------------------------
 0.94 - 0.84    1713   1778     96.3     4.45      1.95    4.53  0.2419  0.1747
  Inf - 0.84    6150   6215     99.0    10.56      8.35   19.19  0.0700  0.0345
#-------------------------------------------------------------------------------

 The ions are 8.1(2)% disordered. The disorder is described a non-crystallographic
 mirror symmetry, whereby the mirror plane is located perpendicular to the b-axis
 at approx. y = 1/4.
 The following restraints were made for the minor component:
  SADI C8A C9A C9A C10A C10A C11A
  SADI N2A C8A N2A C11A
  The three phenyl rings in the minor component were restrained with AFIX 66.

 Highest peak    0.42  at  0.0840  0.3957  0.4828  [  0.77 A from F7A ]
 Deepest hole   -0.43  at  0.1803  0.3598  0.1746  [  0.86 A from P1 ]
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0545P)²+5.5132P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.00101(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5738
_refine_ls_number_parameters     508
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_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 0.23325(17) 0.4708(4) 0.30040(16) 0.0209(7) Uani 0.9189(18) 1 d . . P A 1
C2 C 0.24020(17) 0.5749(4) 0.35456(16) 0.0205(7) Uani 0.9189(18) 1 d . . P A 1
C3 C 0.28435(17) 0.4429(4) 0.36603(15) 0.0203(7) Uani 0.9189(18) 1 d . . P A 1
C4 C 0.16334(18) 0.8037(4) 0.34215(17) 0.0262(7) Uani 0.9189(18) 1 d . . P A 1
H4A H 0.122089 0.750508 0.308894 0.031 Uiso 0.9189(18) 1 calc R U P A 1
H4B H 0.183342 0.879925 0.316565 0.031 Uiso 0.9189(18) 1 calc R U P A 1
C5 C 0.13983(19) 0.8760(4) 0.40182(18) 0.0299(8) Uani 0.9189(18) 1 d . . P A 1
H5A H 0.104193 0.811471 0.415685 0.036 Uiso 0.9189(18) 1 calc R U P A 1
H5B H 0.117957 0.976801 0.388321 0.036 Uiso 0.9189(18) 1 calc R U P A 1
C6 C 0.21206(19) 0.8879(4) 0.46095(17) 0.0280(8) Uani 0.9189(18) 1 d . . P A 1
H6A H 0.202868 0.896326 0.506934 0.034 Uiso 0.9189(18) 1 calc R U P A 1
H6B H 0.240684 0.976566 0.454145 0.034 Uiso 0.9189(18) 1 calc R U P A 1
C7 C 0.2528(3) 0.7392(4) 0.4558(3) 0.0246(11) Uani 0.9189(18) 1 d . . P A 1
H7A H 0.306200 0.755774 0.467443 0.030 Uiso 0.9189(18) 1 calc R U P A 1
H7B H 0.243046 0.660821 0.487126 0.030 Uiso 0.9189(18) 1 calc R U P A 1
C8 C 0.34985(19) 0.2013(5) 0.38832(17) 0.0249(7) Uani 0.9189(18) 1 d . . P A 1
H8A H 0.372776 0.202102 0.349974 0.030 Uiso 0.9189(18) 1 calc R U P A 1
H8B H 0.304945 0.138946 0.374231 0.030 Uiso 0.9189(18) 1 calc R U P A 1
C9 C 0.4035(2) 0.1431(4) 0.45682(18) 0.0335(9) Uani 0.9189(18) 1 d . . P A 1
H9A H 0.377178 0.088140 0.485138 0.040 Uiso 0.9189(18) 1 calc R U P A 1
H9B H 0.440455 0.075155 0.447194 0.040 Uiso 0.9189(18) 1 calc R U P A 1
C10 C 0.4395(2) 0.2868(5) 0.4944(2) 0.0296(8) Uani 0.9189(18) 1 d . . P A 1
H10A H 0.460484 0.268971 0.545200 0.036 Uiso 0.9189(18) 1 calc R U P A 1
H10B H 0.478530 0.323168 0.475190 0.036 Uiso 0.9189(18) 1 calc R U P A 1
C11 C 0.37595(19) 0.3994(4) 0.47980(17) 0.0255(8) Uani 0.9189(18) 1 d . . P A 1
H11A H 0.346579 0.385621 0.512635 0.031 Uiso 0.9189(18) 1 calc R U P A 1
H11B H 0.393615 0.504842 0.482549 0.031 Uiso 0.9189(18) 1 calc R U P A 1
C12 C 0.26741(18) 0.3193(4) 0.18703(16) 0.0203(8) Uani 0.9189(18) 1 d . . P A 1
C13 C 0.30927(18) 0.4012(4) 0.15183(18) 0.0238(7) Uani 0.9189(18) 1 d . . P A 1
H13 H 0.296996 0.502619 0.137927 0.029 Uiso 0.9189(18) 1 calc R U P A 1
C14 C 0.3688(2) 0.3316(4) 0.13768(17) 0.0271(9) Uani 0.9189(18) 1 d . . P A 1
H14 H 0.397608 0.386266 0.114540 0.033 Uiso 0.9189(18) 1 calc R U P A 1
C15 C 0.38622(19) 0.1828(5) 0.15725(17) 0.0278(9) Uani 0.9189(18) 1 d . . P A 1
H15 H 0.426803 0.136420 0.147307 0.033 Uiso 0.9189(18) 1 calc R U P A 1
C16 C 0.3447(2) 0.1008(4) 0.19136(17) 0.0269(8) Uani 0.9189(18) 1 d . . P A 1
H16 H 0.356841 -0.001143 0.204355 0.032 Uiso 0.9189(18) 1 calc R U P A 1
C17 C 0.28501(18) 0.1694(4) 0.20642(16) 0.0230(8) Uani 0.9189(18) 1 d . . P A 1
H17 H 0.256624 0.114094 0.229746 0.028 Uiso 0.9189(18) 1 calc R U P A 1
C18 C 0.15949(17) 0.5717(4) 0.16015(15) 0.0209(7) Uani 0.9189(18) 1 d . . P A 1
C19 C 0.09062(18) 0.5649(4) 0.10974(17) 0.0264(7) Uani 0.9189(18) 1 d . . P A 1
H19 H 0.060649 0.478071 0.106184 0.032 Uiso 0.9189(18) 1 calc R U P A 1
C20 C 0.0667(2) 0.6876(4) 0.06491(18) 0.0305(8) Uani 0.9189(18) 1 d . . P A 1
H20 H 0.019711 0.685233 0.031575 0.037 Uiso 0.9189(18) 1 calc R U P A 1
C21 C 0.1112(2) 0.8123(4) 0.06885(18) 0.0308(8) Uani 0.9189(18) 1 d . . P A 1
H21 H 0.095431 0.892898 0.036661 0.037 Uiso 0.9189(18) 1 calc R U P A 1
C22 C 0.1793(2) 0.8210(4) 0.11986(18) 0.0293(8) Uani 0.9189(18) 1 d . . P A 1
H22 H 0.208946 0.908270 0.122801 0.035 Uiso 0.9189(18) 1 calc R U P A 1
C23 C 0.20367(18) 0.7014(4) 0.16637(17) 0.0254(7) Uani 0.9189(18) 1 d . . P A 1
H23 H 0.249313 0.707438 0.201678 0.030 Uiso 0.9189(18) 1 calc R U P A 1
C24 C 0.12473(18) 0.2750(4) 0.21115(18) 0.0216(8) Uani 0.9189(18) 1 d . . P A 1
C25 C 0.0983(2) 0.2569(4) 0.2693(2) 0.0250(8) Uani 0.9189(18) 1 d . . P A 1
H25 H 0.120145 0.310260 0.311464 0.030 Uiso 0.9189(18) 1 calc R U P A 1
C26 C 0.03942(19) 0.1590(4) 0.26416(19) 0.0320(8) Uani 0.9189(18) 1 d . . P A 1
H26 H 0.020771 0.146363 0.302842 0.038 Uiso 0.9189(18) 1 calc R U P A 1
C27 C 0.00813(19) 0.0802(4) 0.2023(2) 0.0343(9) Uani 0.9189(18) 1 d . . P A 1
H27 H -0.031977 0.014640 0.199192 0.041 Uiso 0.9189(18) 1 calc R U P A 1
C28 C 0.03485(19) 0.0963(4) 0.1449(2) 0.0338(8) Uani 0.9189(18) 1 d . . P A 1
H28 H 0.013148 0.041504 0.103131 0.041 Uiso 0.9189(18) 1 calc R U P A 1
C29 C 0.09359(18) 0.1931(4) 0.14896(18) 0.0266(7) Uani 0.9189(18) 1 d . . P A 1
H29 H 0.112446 0.203729 0.110301 0.032 Uiso 0.9189(18) 1 calc R U P A 1
C30 C 0.5206(3) 0.2354(7) 0.3194(2) 0.0314(11) Uani 0.9189(18) 1 d . . P A 1
H30A H 0.537096 0.226525 0.277150 0.038 Uiso 0.9189(18) 1 calc R U P A 1
H30B H 0.489852 0.146512 0.321248 0.038 Uiso 0.9189(18) 1 calc R U P A 1
B1 B 0.3825(2) 0.7969(4) 0.3328(2) 0.0232(8) Uani 0.9189(18) 1 d . . P A 1
B2 B 0.1571(2) 0.3214(5) 0.4718(2) 0.0296(9) Uani 0.9189(18) 1 d . . P A 1
N1 N 0.22092(14) 0.6961(3) 0.38056(13) 0.0215(6) Uani 0.9189(18) 1 d . . P A 1
N2 N 0.33357(15) 0.3582(3) 0.40733(14) 0.0224(7) Uani 0.9189(18) 1 d . . P A 1
F1 F 0.39215(13) 0.7184(3) 0.39544(13) 0.0393(6) Uani 0.9189(18) 1 d . . P A 1
F2 F 0.32071(11) 0.8896(2) 0.31977(11) 0.0368(5) Uani 0.9189(18) 1 d . . P A 1
F3 F 0.44488(11) 0.8829(2) 0.33623(11) 0.0367(5) Uani 0.9189(18) 1 d . . P A 1
F4 F 0.37113(12) 0.6919(3) 0.27795(12) 0.0418(6) Uani 0.9189(18) 1 d . . P A 1
F5 F 0.19792(13) 0.2493(3) 0.43292(14) 0.0365(6) Uani 0.9189(18) 1 d . . P A 1
F6 F 0.11366(18) 0.4285(4) 0.42813(14) 0.0879(11) Uani 0.9189(18) 1 d . . P A 1
F7 F 0.11811(17) 0.2138(4) 0.49575(16) 0.0767(9) Uani 0.9189(18) 1 d . . P A 1
F8 F 0.20538(13) 0.3940(2) 0.52836(11) 0.0476(6) Uani 0.9189(18) 1 d . . P A 1
P1 P 0.19561(4) 0.40909(9) 0.21332(4) 0.0193(2) Uani 0.9189(18) 1 d . . P A 1
Cl1 Cl 0.5979(2) 0.2385(5) 0.39508(18) 0.0398(6) Uani 0.9189(18) 1 d . . P A 1
Cl2 Cl 0.46801(5) 0.40252(10) 0.31423(5) 0.0337(2) Uani 0.9189(18) 1 d . . P A
1
C1A C 0.232(2) 0.031(5) 0.299(2) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
C2A C 0.241(2) -0.073(5) 0.353(2) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
C3A C 0.286(2) 0.055(5) 0.368(2) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
C4A C 0.163(2) -0.294(6) 0.345(2) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
H4AA H 0.179414 -0.369546 0.316028 0.040 Uiso 0.0811(18) 1 calc R U P A 2
H4AB H 0.123041 -0.233062 0.314090 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C5A C 0.139(2) -0.372(5) 0.404(2) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
H5AA H 0.103034 -0.308708 0.419154 0.040 Uiso 0.0811(18) 1 calc R U P A 2
H5AB H 0.116894 -0.472328 0.389908 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C6A C 0.212(2) -0.385(5) 0.463(2) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
H6AA H 0.244034 -0.463570 0.452545 0.040 Uiso 0.0811(18) 1 calc R U P A 2
H6AB H 0.204442 -0.406725 0.508965 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C7A C 0.246(4) -0.221(8) 0.462(4) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
H7AA H 0.224004 -0.144736 0.485954 0.040 Uiso 0.0811(18) 1 calc R U P A 2
H7AB H 0.299868 -0.219734 0.481094 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C8A C 0.350(3) 0.302(7) 0.396(2) 0.0336(19) Uiso 0.0811(18) 1 d D U P A 2
H8AA H 0.302530 0.357704 0.382327 0.040 Uiso 0.0811(18) 1 calc R U P A 2
H8AB H 0.373675 0.314759 0.358690 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C9A C 0.399(3) 0.357(5) 0.466(2) 0.0336(19) Uiso 0.0811(18) 1 d D U P A 2
H9AA H 0.431838 0.439069 0.460087 0.040 Uiso 0.0811(18) 1 calc R U P A 2
H9AB H 0.369804 0.394143 0.496416 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C10A C 0.442(3) 0.217(4) 0.496(3) 0.0336(19) Uiso 0.0811(18) 1 d D U P A 2
H10C H 0.478483 0.191193 0.472134 0.040 Uiso 0.0811(18) 1 calc R U P A 2
H10D H 0.465893 0.226203 0.547017 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C11A C 0.380(2) 0.103(5) 0.481(2) 0.0336(19) Uiso 0.0811(18) 1 d D U P A 2
H11C H 0.398721 -0.001981 0.483719 0.040 Uiso 0.0811(18) 1 calc R U P A 2
H11D H 0.349658 0.114470 0.512778 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C12A C 0.2664(18) 0.183(4) 0.188(2) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
C13A C 0.311(2) 0.107(3) 0.156(2) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H13A H 0.303118 0.002802 0.145127 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C14A C 0.3681(19) 0.182(4) 0.141(2) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H14A H 0.398723 0.130331 0.118602 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C15A C 0.3800(19) 0.335(4) 0.157(2) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H15A H 0.418811 0.386342 0.146145 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C16A C 0.335(2) 0.411(3) 0.189(2) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H16A H 0.343292 0.514826 0.200213 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C17A C 0.2783(19) 0.335(4) 0.205(2) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H17A H 0.247686 0.387300 0.226739 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C18A C 0.1546(14) -0.070(3) 0.1592(13) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
C19A C 0.0873(13) -0.060(2) 0.1085(13) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H19A H 0.058232 0.028257 0.105461 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C20A C 0.0624(12) -0.178(3) 0.0621(12) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H20A H 0.016389 -0.171237 0.027404 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C21A C 0.1049(15) -0.307(3) 0.0665(13) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H21A H 0.087918 -0.388280 0.034785 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C22A C 0.1723(14) -0.318(3) 0.1172(15) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H22A H 0.201290 -0.405830 0.120224 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C23A C 0.1971(11) -0.199(3) 0.1636(13) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H23A H 0.243134 -0.206337 0.198282 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C24A C 0.1218(18) 0.225(4) 0.2090(19) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
C25A C 0.095(2) 0.238(4) 0.2662(15) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H25A H 0.115938 0.179320 0.306940 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C26A C 0.0381(17) 0.337(4) 0.2640(12) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H26A H 0.019921 0.345845 0.303135 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C27A C 0.0077(13) 0.423(3) 0.2044(13) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H27A H -0.031296 0.490369 0.202894 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C28A C 0.0343(15) 0.410(3) 0.1472(11) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H28A H 0.013502 0.468367 0.106456 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C29A C 0.0913(16) 0.311(3) 0.1494(14) 0.0336(19) Uiso 0.0811(18) 1 d G U P A 2
H29A H 0.109518 0.301842 0.110260 0.040 Uiso 0.0811(18) 1 calc R U P A 2
C30A C 0.530(4) 0.227(10) 0.304(4) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
H30C H 0.548060 0.199374 0.264561 0.040 Uiso 0.0811(18) 1 calc R U P A 2
H30D H 0.502401 0.323316 0.293604 0.040 Uiso 0.0811(18) 1 calc R U P A 2
B1A B 0.380(3) 0.685(6) 0.333(3) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
B2A B 0.152(3) 0.183(6) 0.466(3) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
N1A N 0.218(2) -0.207(5) 0.3799(19) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
N2A N 0.338(2) 0.142(4) 0.4085(18) 0.0336(19) Uiso 0.0811(18) 1 d D U P A 2
F1A F 0.3908(18) 0.784(3) 0.3951(18) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
F2A F 0.3160(12) 0.606(3) 0.3241(11) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
F3A F 0.4376(12) 0.595(3) 0.3367(11) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
F4A F 0.3680(13) 0.784(3) 0.2718(13) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
F5A F 0.1729(17) 0.226(4) 0.435(2) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
F6A F 0.1122(12) 0.073(3) 0.4248(11) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
F7A F 0.0994(13) 0.317(3) 0.4953(12) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
F8A F 0.2065(12) 0.102(3) 0.5272(11) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
P1A P 0.1941(6) 0.0931(13) 0.2139(6) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
Cl1A Cl 0.606(3) 0.240(6) 0.387(3) 0.0336(19) Uiso 0.0811(18) 1 d . U P A 2
Cl2A Cl 0.4681(5) 0.0626(11) 0.3263(5) 0.0336(19) Uiso 0.0811(18) 1 d . U P 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.400(4) . ?
C1 C3 1.410(4) . ?
C1 P1 1.767(3) . ?
C2 N1 1.294(4) . ?
C2 C3 1.421(4) . ?
C3 N2 1.295(4) . ?
C4 N1 1.489(4) . ?
C4 C5 1.535(5) . ?
C5 C6 1.537(5) . ?
C6 C7 1.550(5) . ?
C7 N1 1.499(5) . ?
C8 N2 1.499(4) . ?
C8 C9 1.541(5) . ?
C9 C10 1.535(6) . ?
C10 C11 1.533(5) . ?
C11 N2 1.485(4) . ?
C12 C17 1.397(5) . ?
C12 C13 1.413(5) . ?
C12 P1 1.795(3) . ?
C13 C14 1.396(5) . ?
C14 C15 1.387(5) . ?
C15 C16 1.394(5) . ?
C16 C17 1.403(5) . ?
C18 C19 1.406(5) . ?
C18 C23 1.411(5) . ?
C18 P1 1.804(3) . ?
C19 C20 1.398(5) . ?
C20 C21 1.383(5) . ?
C21 C22 1.402(5) . ?
C22 C23 1.398(5) . ?
C24 C25 1.409(5) . ?
C24 C29 1.413(5) . ?
C24 P1 1.794(3) . ?
C25 C26 1.402(6) . ?
C26 C27 1.395(5) . ?
C27 C28 1.397(5) . ?
C28 C29 1.397(5) . ?
C30 Cl2 1.776(6) . ?
C30 Cl1 1.781(7) . ?
B1 F1 1.398(5) . ?
B1 F2 1.399(4) . ?
B1 F3 1.401(4) . ?
B1 F4 1.408(5) . ?
B2 F7 1.380(5) . ?
B2 F6 1.388(5) . ?
B2 F8 1.392(5) . ?
B2 F5 1.408(5) . ?
C1A C2A 1.39(6) . ?
C1A C3A 1.47(6) . ?
C1A P1A 1.74(4) . ?
C2A C3A 1.40(6) . ?
C2A N1A 1.42(6) . ?
C3A N2A 1.33(6) . ?
C4A N1A 1.33(6) . ?
C4A C5A 1.57(6) . ?
C5A C6A 1.55(6) . ?
C6A C7A 1.59(8) . ?
C7A N1A 1.58(9) . ?
C8A N2A 1.47(4) . ?
C8A C9A 1.53(4) . ?
C9A C10A 1.52(4) . ?
C10A C11A 1.51(4) . ?
C11A N2A 1.47(4) . ?
C12A C13A 1.3900 . ?
C12A C17A 1.3900 . ?
C12A P1A 1.80(3) . ?
C13A C14A 1.3900 . ?
C14A C15A 1.3900 . ?
C15A C16A 1.3900 . ?
C16A C17A 1.3900 . ?
C18A C19A 1.3900 . ?
C18A C23A 1.3900 . ?
C18A P1A 1.84(2) . ?
C19A C20A 1.3900 . ?
C20A C21A 1.3900 . ?
C21A C22A 1.3900 . ?
C22A C23A 1.3900 . ?
C24A C25A 1.3900 . ?
C24A C29A 1.3900 . ?
C24A P1A 1.79(2) . ?
C25A C26A 1.3900 . ?
C26A C27A 1.3900 . ?
C27A C28A 1.3900 . ?
C28A C29A 1.3900 . ?
C30A Cl1A 1.86(10) . ?
C30A Cl2A 2.01(8) . ?
B1A F3A 1.35(6) . ?
B1A F2A 1.37(6) . ?
B1A F4A 1.46(6) . ?
B1A F1A 1.49(6) . ?
B2A F5A 0.91(5) . ?
B2A F6A 1.35(5) . ?
B2A F8A 1.54(6) . ?
B2A F7A 1.77(6) . ?
F5A F6A 1.76(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 C3 60.7(2) . . ?
C2 C1 P1 152.5(3) . . ?
C3 C1 P1 146.7(3) . . ?
N1 C2 C1 152.3(3) . . ?
N1 C2 C3 147.6(3) . . ?
C1 C2 C3 60.0(2) . . ?
N2 C3 C1 150.6(3) . . ?
N2 C3 C2 150.0(3) . . ?
C1 C3 C2 59.3(2) . . ?
N1 C4 C5 101.9(3) . . ?
C4 C5 C6 103.0(3) . . ?
C5 C6 C7 104.2(3) . . ?
N1 C7 C6 102.7(3) . . ?
N2 C8 C9 102.6(3) . . ?
C10 C9 C8 104.2(3) . . ?
C11 C10 C9 103.3(3) . . ?
N2 C11 C10 101.6(3) . . ?
C17 C12 C13 120.1(3) . . ?
C17 C12 P1 118.9(3) . . ?
C13 C12 P1 120.9(3) . . ?
C14 C13 C12 119.4(3) . . ?
C15 C14 C13 120.3(3) . . ?
C14 C15 C16 120.7(3) . . ?
C15 C16 C17 119.7(3) . . ?
C12 C17 C16 119.8(3) . . ?
C19 C18 C23 120.6(3) . . ?
C19 C18 P1 120.4(2) . . ?
C23 C18 P1 118.9(2) . . ?
C20 C19 C18 119.2(3) . . ?
C21 C20 C19 120.3(3) . . ?
C20 C21 C22 120.7(3) . . ?
C23 C22 C21 120.0(3) . . ?
C22 C23 C18 119.1(3) . . ?
C25 C24 C29 120.7(3) . . ?
C25 C24 P1 120.5(3) . . ?
C29 C24 P1 118.8(3) . . ?
C26 C25 C24 119.0(4) . . ?
C27 C26 C25 120.1(3) . . ?
C26 C27 C28 121.0(3) . . ?
C27 C28 C29 119.8(3) . . ?
C28 C29 C24 119.4(3) . . ?
Cl2 C30 Cl1 110.6(3) . . ?
F1 B1 F2 110.0(3) . . ?
F1 B1 F3 109.9(3) . . ?
F2 B1 F3 110.5(3) . . ?
F1 B1 F4 108.7(3) . . ?
F2 B1 F4 108.3(3) . . ?
F3 B1 F4 109.3(3) . . ?
F7 B2 F6 114.0(4) . . ?
F7 B2 F8 109.4(3) . . ?
F6 B2 F8 109.1(3) . . ?
F7 B2 F5 108.8(3) . . ?
F6 B2 F5 106.8(3) . . ?
F8 B2 F5 108.4(3) . . ?
C2 N1 C4 125.4(3) . . ?
C2 N1 C7 122.4(3) . . ?
C4 N1 C7 112.1(3) . . ?
C3 N2 C11 124.6(3) . . ?
C3 N2 C8 122.8(3) . . ?
C11 N2 C8 112.4(3) . . ?
C1 P1 C24 108.36(15) . . ?
C1 P1 C12 107.56(15) . . ?
C24 P1 C12 109.71(16) . . ?
C1 P1 C18 108.05(15) . . ?
C24 P1 C18 111.04(15) . . ?
C12 P1 C18 111.98(15) . . ?
C2A C1A C3A 59(3) . . ?
C2A C1A P1A 153(4) . . ?
C3A C1A P1A 148(3) . . ?
C1A C2A C3A 63(3) . . ?
C1A C2A N1A 150(4) . . ?
C3A C2A N1A 147(4) . . ?
N2A C3A C2A 154(4) . . ?
N2A C3A C1A 148(4) . . ?
C2A C3A C1A 58(3) . . ?
N1A C4A C5A 103(4) . . ?
C6A C5A C4A 102(3) . . ?
C5A C6A C7A 102(4) . . ?
N1A C7A C6A 94(5) . . ?
N2A C8A C9A 103(3) . . ?
C10A C9A C8A 103(4) . . ?
C11A C10A C9A 100(4) . . ?
N2A C11A C10A 102(4) . . ?
C13A C12A C17A 120.0 . . ?
C13A C12A P1A 123(2) . . ?
C17A C12A P1A 117(2) . . ?
C14A C13A C12A 120.0 . . ?
C13A C14A C15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C17A C16A C15A 120.0 . . ?
C16A C17A C12A 120.0 . . ?
C19A C18A C23A 120.0 . . ?
C19A C18A P1A 120.9(15) . . ?
C23A C18A P1A 118.7(15) . . ?
C18A C19A C20A 120.0 . . ?
C21A C20A C19A 120.0 . . ?
C20A C21A C22A 120.0 . . ?
C21A C22A C23A 120.0 . . ?
C22A C23A C18A 120.0 . . ?
C25A C24A C29A 120.0 . . ?
C25A C24A P1A 118.2(19) . . ?
C29A C24A P1A 121.8(19) . . ?
C24A C25A C26A 120.0 . . ?
C27A C26A C25A 120.0 . . ?
C26A C27A C28A 120.0 . . ?
C29A C28A C27A 120.0 . . ?
C28A C29A C24A 120.0 . . ?
Cl1A C30A Cl2A 102(4) . . ?
F3A B1A F2A 113(4) . . ?
F3A B1A F4A 109(4) . . ?
F2A B1A F4A 107(4) . . ?
F3A B1A F1A 113(4) . . ?
F2A B1A F1A 108(4) . . ?
F4A B1A F1A 107(4) . . ?
F5A B2A F6A 100(5) . . ?
F5A B2A F8A 114(5) . . ?
F6A B2A F8A 106(4) . . ?
F5A B2A F7A 110(5) . . ?
F6A B2A F7A 114(4) . . ?
F8A B2A F7A 111(3) . . ?
C4A N1A C2A 125(4) . . ?
C4A N1A C7A 118(4) . . ?
C2A N1A C7A 114(4) . . ?
C3A N2A C11A 124(4) . . ?
C3A N2A C8A 125(3) . . ?
C11A N2A C8A 109(4) . . ?
B2A F5A F6A 49(4) . . ?
B2A F6A F5A 31(2) . . ?
C1A P1A C24A 110.7(18) . . ?
C1A P1A C12A 107(2) . . ?
C24A P1A C12A 110.0(19) . . ?
C1A P1A C18A 108.4(18) . . ?
C24A P1A C18A 107.8(17) . . ?
C12A P1A C18A 113.3(16) . . ?

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_9295sadabs
_database_code_depnum_ccdc_archive 'CCDC 1564416'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT03197A 2017
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;
_audit_block_code                9295
_chemical_compound_source        dichloromethan,pentane






_audit_creation_date             2015-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 Title
;
_chemical_formula_moiety         '2(C24 H22 N P) 4(C F3 O3 S) (C4 H8 O)'
_chemical_formula_sum            'C56 H52 F12 N2 O13 P2 S4'
_chemical_formula_weight         1379.17

_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'c 2/c'
_symmetry_space_group_name_Hall  '-c 2yc (#15:b1)'
_symmetry_Int_Tables_number      15

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   26.974(4)
_cell_length_b                   14.0542(18)
_cell_length_c                   17.075(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.586(3)
_cell_angle_gamma                90
_cell_volume                     6135.7(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9692


_cell_measurement_temperature    100
_cell_measurement_theta_max      31.0530
_cell_measurement_theta_min      2.5133
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.98565
_exptl_absorpt_correction_T_min  0.94315

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.1000
0.00 -1.00 0.00 0.0800
1.00 0.00 -1.00 0.0250
-1.00 0.00 1.00 0.0250
-1.00 0.00 0.00 0.1100
1.00 0.00 0.00 0.1100
0.00 -1.00 1.00 0.0700
-1.00 2.00 -1.00 0.1000
_exptl_crystal_description       plate
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            136310
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.313
_diffrn_reflns_theta_min         1.593
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   1\mS
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8913
_reflns_number_total             13021
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'

_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_refine_diff_density_max         1.317
_refine_diff_density_min         -1.222
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         13021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0935P)²+18.8604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.2005

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.9250 and 1.0000 (SADABS).

Highest peak        ?
Deepest hole        ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C26B)=1-FVAR(1)
 Sof(C26A)=FVAR(1)
 Fixed Sof: F4B(0.5) F6B(0.5) F5A(0.5) C2B(0.5) H2B(0.5) H5B(0.5) H5A(0.5)
 C4B(0.5) H4B(0.5) C3B(0.5) H3B(0.5) C30(0.5) H30A(0.5) H30B(0.5) C27(0.5)
 H27A(0.5) H27B(0.5) O7(0.5) C28(0.5) H28A(0.5) H28B(0.5) C29(0.5) H29A(0.5)
 H29B(0.5) F4A(0.5) F6A(0.5) F5B(0.5) C4A(0.5) H4A(0.5) C3A(0.5) H3A(0.5)
 C2A(0.5) H2A(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B)
3.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C8(H8), C22(H22), C21(H21), C23(H23), C12(H12), C18(H18), C14(H14),
 C17(H17), C9(H9), C6(H6), C15(H15), C16(H16), C10(H10), C11(H11), C2B(H2B),
 C5(H5B), C5(H5A), C4B(H4B), C3B(H3B), C4A(H4A), C3A(H3A), C2A(H2A)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
P1 P 0.09675(2) 0.26402(3) 0.13884(3) 0.01474(10) Uani 1 1 d . . . . .
S2 S 0.31025(2) 0.17273(4) 0.26104(3) 0.02347(11) Uani 1 1 d . . . . .
N1 N 0.15038(7) -0.00305(12) 0.15253(11) 0.0208(3) Uani 1 1 d . . . . .
C13 C 0.13808(7) 0.30305(13) 0.08124(11) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.03106(7) 0.30083(14) 0.08637(12) 0.0200(3) Uani 1 1 d . . . . .
C19 C 0.10012(7) 0.13612(13) 0.14563(11) 0.0158(3) Uani 1 1 d . . . . .
C7 C 0.11993(7) 0.30939(13) 0.24181(11) 0.0171(3) Uani 1 1 d . . . . .
C20 C 0.05994(8) 0.08190(14) 0.15819(12) 0.0197(3) Uani 1 1 d . . . . .
H20 H 0.0287 0.1114 0.1604 0.024 Uiso 1 1 calc R . . . .
O4 O 0.27257(6) 0.12963(12) 0.19038(10) 0.0286(3) Uani 1 1 d . . . . .
C8 C 0.14075(8) 0.40129(14) 0.25562(12) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.1423 0.4396 0.2106 0.025 Uiso 1 1 calc R . . . .
C22 C 0.11203(8) -0.05698(14) 0.16457(13) 0.0233(4) Uani 1 1 d . . . . .
H22 H 0.1166 -0.1239 0.1711 0.028 Uiso 1 1 calc R . . . .
C21 C 0.06648(8) -0.01605(15) 0.16743(13) 0.0231(4) Uani 1 1 d . . . . .
H21 H 0.0396 -0.0544 0.1757 0.028 Uiso 1 1 calc R . . . .
C23 C 0.14533(7) 0.09154(13) 0.14292(11) 0.0178(3) Uani 1 1 d . . . . .
H23 H 0.1728 0.1280 0.1343 0.021 Uiso 1 1 calc R . . . .
O5 O 0.31587(9) 0.27309(14) 0.25318(12) 0.0432(5) Uani 1 1 d . . . . .
C12 C 0.11659(9) 0.25319(15) 0.30793(12) 0.0226(4) Uani 1 1 d . . . . .
H12 H 0.1017 0.1913 0.2981 0.027 Uiso 1 1 calc R . . . .
C18 C 0.19179(7) 0.31408(14) 0.12065(12) 0.0192(3) Uani 1 1 d . . . . .
H18 H 0.2062 0.3058 0.1787 0.023 Uiso 1 1 calc R . . . .
F4B F 0.30183(16) 0.1964(3) 0.4105(2) 0.0387(9) Uiso 0.5 1 d . . P A 2
C14 C 0.11669(8) 0.31541(17) -0.00434(13) 0.0251(4) Uani 1 1 d . . . . .
H14 H 0.0802 0.3080 -0.0310 0.030 Uiso 1 1 calc R . . . .
C17 C 0.22411(8) 0.33741(15) 0.07395(13) 0.0232(4) Uani 1 1 d . . . . .
H17 H 0.2607 0.3448 0.1003 0.028 Uiso 1 1 calc R . . . .
C24 C 0.19836(8) -0.05027(15) 0.14709(17) 0.0293(4) Uani 1 1 d . . . . .
H24A H 0.2137 -0.0893 0.1965 0.044 Uiso 1 1 calc GR . . . .
H24B H 0.2237 -0.0019 0.1433 0.044 Uiso 1 1 calc GR . . . .
H24C H 0.1894 -0.0909 0.0979 0.044 Uiso 1 1 calc GR . . . .
O6 O 0.35871(8) 0.12118(17) 0.29418(13) 0.0465(5) Uani 1 1 d . . . . .
C9 C 0.15923(9) 0.43606(16) 0.33618(13) 0.0265(4) Uani 1 1 d . . . . .
H9 H 0.1736 0.4983 0.3463 0.032 Uiso 1 1 calc R . . . .
C6 C -0.00126(9) 0.24931(17) 0.01985(13) 0.0264(4) Uani 1 1 d . . . . .
H6 H 0.0091 0.1884 0.0065 0.032 Uiso 1 1 calc R . . . .
C15 C 0.14970(9) 0.33878(18) -0.04998(13) 0.0288(4) Uani 1 1 d . . . . .
H15 H 0.1356 0.3471 -0.1081 0.035 Uiso 1 1 calc R . . . .
C16 C 0.20295(9) 0.34984(16) -0.01089(13) 0.0254(4) Uani 1 1 d . . . . .
H16 H 0.2251 0.3660 -0.0423 0.031 Uiso 1 1 calc R . . . .
C10 C 0.15658(11) 0.37986(18) 0.40158(14) 0.0336(5) Uani 1 1 d . . . . .
H10 H 0.1695 0.4038 0.4564 0.040 Uiso 1 1 calc R . . . .
C11 C 0.13520(11) 0.28876(17) 0.38791(14) 0.0323(5) Uani 1 1 d . . . . .
H11 H 0.1334 0.2511 0.4331 0.039 Uiso 1 1 calc R . . . .
F6B F 0.22948(14) 0.1814(3) 0.3149(2) 0.0360(7) Uiso 0.5 1 d . . P A 2
F5A F 0.2699(2) 0.0804(4) 0.3626(3) 0.0538(12) Uiso 0.5 1 d . . P A 1
C2B C 0.01705(17) 0.3944(3) 0.0968(3) 0.0202(8) Uiso 0.5 1 d . . P B 2
H2B H 0.0404 0.4332 0.1377 0.024 Uiso 0.5 1 calc R . P B 2
C26B C 0.2773(5) 0.1461(17) 0.3371(7) 0.016(4) Uiso 0.25(5) 1 d . . P A 2
C5 C -0.04906(9) 0.2888(2) -0.02683(15) 0.0323(5) Uani 1 1 d . . . . .
H5B H -0.0724 0.2511 -0.0687 0.039 Uiso 0.5 1 calc R . P C 2
H5A H -0.0707 0.2575 -0.0749 0.039 Uiso 0.5 1 calc R . P D 1
C4B C -0.0632(3) 0.3761(5) -0.0154(4) 0.0260(14) Uiso 0.5 1 d . . P B 2
H4B H -0.0954 0.4010 -0.0502 0.031 Uiso 0.5 1 calc R . P B 2
S1 S 0.08294(2) -0.01022(4) -0.07800(3) 0.02382(12) Uani 1 1 d . . . . .
F2 F 0.17184(6) 0.08150(13) -0.02437(10) 0.0421(4) Uani 1 1 d . . . . .
O1 O 0.05406(6) -0.04673(15) -0.15850(10) 0.0338(4) Uani 1 1 d . . . . .
F1 F 0.16487(7) -0.01095(16) -0.12899(14) 0.0568(6) Uani 1 1 d . . . . .
O2 O 0.05912(8) 0.06596(17) -0.04699(13) 0.0458(5) Uani 1 1 d . . . . .
F3 F 0.12466(10) 0.12025(15) -0.14726(11) 0.0590(6) Uani 1 1 d . . . . .
O3 O 0.10719(9) -0.08345(15) -0.01851(12) 0.0435(5) Uani 1 1 d . . . . .
C25 C 0.13875(10) 0.04739(19) -0.09562(16) 0.0328(5) Uani 1 1 d . . . . .
C3B C -0.03091(17) 0.4318(3) 0.0478(3) 0.0228(8) Uiso 0.5 1 d . . P B 2
H3B H -0.0412 0.4941 0.0576 0.027 Uiso 0.5 1 calc R . P B 2
C30 C -0.0005(4) 0.7370(6) 0.2926(6) 0.0580(19) Uiso 0.5 1 d . . P E 3
H30A H -0.0390 0.7447 0.2728 0.070 Uiso 0.5 1 calc R . P E 3
H30B H 0.0154 0.7884 0.3323 0.070 Uiso 0.5 1 calc R . P E 3
C27 C 0.0191(3) 0.6315(5) 0.2012(4) 0.0451(13) Uiso 0.5 1 d . . P E 3
H27A H 0.0084 0.6256 0.1403 0.054 Uiso 0.5 1 calc R . P E 3
H27B H 0.0544 0.6033 0.2245 0.054 Uiso 0.5 1 calc R . P E 3
O7 O -0.0175(2) 0.5797(5) 0.2318(4) 0.0803(18) Uiso 0.5 1 d . . P E 3
C28 C 0.0153(3) 0.6404(5) 0.3295(4) 0.0503(14) Uiso 0.5 1 d . . P E 3
H28A H 0.0002 0.6245 0.3737 0.060 Uiso 0.5 1 calc R . P E 3
H28B H 0.0537 0.6307 0.3491 0.060 Uiso 0.5 1 calc R . P E 3
C29 C 0.0210(3) 0.7345(5) 0.2244(5) 0.0477(15) Uiso 0.5 1 d . . P E 3
H29A H 0.0574 0.7584 0.2420 0.057 Uiso 0.5 1 calc R . P E 3
H29B H -0.0004 0.7733 0.1774 0.057 Uiso 0.5 1 calc R . P E 3
F4A F 0.31372(14) 0.2146(2) 0.4113(2) 0.0273(7) Uiso 0.5 1 d . . P A 1
F6A F 0.23606(14) 0.2171(3) 0.3216(2) 0.0387(7) Uiso 0.5 1 d . . P A 1
F5B F 0.28268(18) 0.0622(3) 0.3593(3) 0.0457(10) Uiso 0.5 1 d . . P A 2
C4A C -0.0650(3) 0.3780(5) -0.0006(5) 0.0316(17) Uiso 0.5 1 d . . P B 1
H4A H -0.0964 0.4078 -0.0334 0.038 Uiso 0.5 1 calc R . P B 1
C3A C -0.0351(2) 0.4200(4) 0.0716(4) 0.0341(11) Uiso 0.5 1 d . . P B 1
H3A H -0.0478 0.4756 0.0906 0.041 Uiso 0.5 1 calc R . P B 1
C2A C 0.01323(18) 0.3831(3) 0.1175(3) 0.0242(9) Uiso 0.5 1 d . . P B 1
H2A H 0.0336 0.4119 0.1678 0.029 Uiso 0.5 1 calc R . P B 1
C26A C 0.2812(2) 0.1673(10) 0.3433(4) 0.0324(11) Uiso 0.75(5) 1 d . . P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C13 1.7917(18) . ?
P1 C1 1.7883(19) . ?
P1 C19 1.8018(18) . ?
P1 C7 1.7856(19) . ?
S2 O4 1.4401(15) . ?
S2 O5 1.4294(19) . ?
S2 O6 1.443(2) . ?
S2 C26B 1.832(9) . ?
S2 C26A 1.815(4) . ?
N1 C22 1.350(3) . ?
N1 C23 1.341(2) . ?
N1 C24 1.483(3) . ?
C13 C18 1.398(3) . ?
C13 C14 1.400(3) . ?
C1 C6 1.394(3) . ?
C1 C2B 1.395(5) . ?
C1 C2A 1.419(5) . ?
C19 C20 1.396(2) . ?
C19 C23 1.385(3) . ?
C7 C8 1.398(3) . ?
C7 C12 1.404(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.372(3) . ?
C21 H21 0.9500 . ?
C23 H23 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.395(3) . ?
F4B C26B 1.41(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.397(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.388(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.397(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.393(3) . ?
C11 H11 0.9500 . ?
F6B C26B 1.319(9) . ?
F5A C26A 1.326(14) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.400(6) . ?
C26B F5B 1.23(2) . ?
C5 H5B 0.9500 . ?
C5 H5A 0.9500 . ?
C5 C4B 1.318(7) . ?
C5 C4A 1.442(8) . ?
C4B H4B 0.9500 . ?
C4B C3B 1.392(8) . ?
S1 O1 1.4412(16) . ?
S1 O2 1.434(2) . ?
S1 O3 1.448(2) . ?
S1 C25 1.817(2) . ?
F2 C25 1.347(3) . ?
F1 C25 1.323(3) . ?
F3 C25 1.325(3) . ?
C3B H3B 0.9500 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C28 1.501(11) . ?
C30 C29 1.458(9) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 O7 1.450(10) . ?
C27 C29 1.497(10) . ?
O7 C28 1.831(10) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
F4A C26A 1.382(12) . ?
F6A C26A 1.350(6) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.372(9) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.390(7) . ?
C2A H2A 0.9500 . ?

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
C13 P1 C19 108.26(8) . . ?
C1 P1 C13 109.09(9) . . ?
C1 P1 C19 110.03(9) . . ?
C7 P1 C13 110.33(9) . . ?
C7 P1 C1 111.72(9) . . ?
C7 P1 C19 107.35(8) . . ?
O4 S2 O6 115.24(11) . . ?
O4 S2 C26B 97.8(7) . . ?
O4 S2 C26A 105.5(4) . . ?
O5 S2 O4 113.84(11) . . ?
O5 S2 O6 114.97(14) . . ?
O5 S2 C26B 111.0(8) . . ?
O5 S2 C26A 101.5(4) . . ?
O6 S2 C26B 101.7(3) . . ?
O6 S2 C26A 103.65(18) . . ?
C22 N1 C24 118.97(17) . . ?
C23 N1 C22 121.49(18) . . ?
C23 N1 C24 119.50(17) . . ?
C18 C13 P1 120.03(14) . . ?
C18 C13 C14 120.51(17) . . ?
C14 C13 P1 119.29(14) . . ?
C6 C1 P1 121.36(16) . . ?
C6 C1 C2B 118.0(2) . . ?
C6 C1 C2A 122.0(3) . . ?
C2B C1 P1 118.3(2) . . ?
C2A C1 P1 116.6(2) . . ?
C20 C19 P1 121.92(14) . . ?
C23 C19 P1 118.43(13) . . ?
C23 C19 C20 119.55(17) . . ?
C8 C7 P1 119.45(14) . . ?
C8 C7 C12 120.63(17) . . ?
C12 C7 P1 119.92(14) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.76(18) . . ?
C21 C20 H20 120.6 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.23(18) . . ?
C9 C8 H8 120.4 . . ?
N1 C22 H22 119.7 . . ?
N1 C22 C21 120.56(18) . . ?
C21 C22 H22 119.7 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.60(18) . . ?
C22 C21 H21 120.2 . . ?
N1 C23 C19 120.03(17) . . ?
N1 C23 H23 120.0 . . ?
C19 C23 H23 120.0 . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.48(19) . . ?
C11 C12 H12 120.3 . . ?
C13 C18 H18 120.3 . . ?
C17 C18 C13 119.43(18) . . ?
C17 C18 H18 120.3 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.18(19) . . ?
C15 C14 H14 120.4 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.13(19) . . ?
C16 C17 H17 119.9 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C1 C6 H6 120.6 . . ?
C1 C6 C5 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C17 C16 H16 119.8 . . ?
C15 C16 C17 120.44(18) . . ?
C15 C16 H16 119.8 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C1 C2B H2B 119.5 . . ?
C1 C2B C3B 120.9(4) . . ?
C3B C2B H2B 119.5 . . ?
F4B C26B S2 109.4(12) . . ?
F6B C26B S2 111.8(6) . . ?
F6B C26B F4B 102.0(12) . . ?
F5B C26B S2 112.1(10) . . ?
F5B C26B F4B 103.3(6) . . ?
F5B C26B F6B 117.2(15) . . ?
C6 C5 H5B 118.5 . . ?
C6 C5 H5A 120.6 . . ?
C6 C5 C4A 118.7(3) . . ?
C4B C5 C6 122.9(3) . . ?
C4B C5 H5B 118.5 . . ?
C4A C5 H5A 120.6 . . ?
C5 C4B H4B 120.0 . . ?
C5 C4B C3B 120.0(5) . . ?
C3B C4B H4B 120.0 . . ?
O1 S1 O3 113.71(12) . . ?
O1 S1 C25 103.01(11) . . ?
O2 S1 O1 116.64(12) . . ?
O2 S1 O3 115.28(14) . . ?
O2 S1 C25 102.77(13) . . ?
O3 S1 C25 102.71(13) . . ?
F2 C25 S1 110.76(16) . . ?
F1 C25 S1 112.23(18) . . ?
F1 C25 F2 108.6(2) . . ?
F1 C25 F3 105.8(2) . . ?
F3 C25 S1 112.2(2) . . ?
F3 C25 F2 107.0(2) . . ?
C2B C3B H3B 120.6 . . ?
C4B C3B C2B 118.9(4) . . ?
C4B C3B H3B 120.6 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30A 111.7 . . ?
C28 C30 H30B 111.7 . . ?
C29 C30 H30A 111.7 . . ?
C29 C30 H30B 111.7 . . ?
C29 C30 C28 100.4(8) . . ?
H27A C27 H27B 108.0 . . ?
O7 C27 H27A 109.4 . . ?
O7 C27 H27B 109.4 . . ?
O7 C27 C29 111.2(6) . . ?
C29 C27 H27A 109.4 . . ?
C29 C27 H27B 109.4 . . ?
C27 O7 C28 84.7(5) . . ?
C30 C28 O7 92.8(6) . . ?
C30 C28 H28A 113.1 . . ?
C30 C28 H28B 113.1 . . ?
O7 C28 H28A 113.1 . . ?
O7 C28 H28B 113.1 . . ?
H28A C28 H28B 110.5 . . ?
C30 C29 C27 104.2(7) . . ?
C30 C29 H29A 110.9 . . ?
C30 C29 H29B 110.9 . . ?
C27 C29 H29A 110.9 . . ?
C27 C29 H29B 110.9 . . ?
H29A C29 H29B 108.9 . . ?
C5 C4A H4A 119.8 . . ?
C3A C4A C5 120.3(6) . . ?
C3A C4A H4A 119.8 . . ?
C4A C3A H3A 119.2 . . ?
C4A C3A C2A 121.5(6) . . ?
C2A C3A H3A 119.2 . . ?
C1 C2A H2A 121.2 . . ?
C3A C2A C1 117.5(4) . . ?
C3A C2A H2A 121.2 . . ?
F5A C26A S2 115.0(8) . . ?
F5A C26A F4A 111.7(4) . . ?
F5A C26A F6A 106.6(6) . . ?
F4A C26A S2 108.4(6) . . ?
F6A C26A S2 109.9(3) . . ?
F6A C26A F4A 104.8(8) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'


_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_chemical_absolute_configuration rmad

####################################################################### 
# 
# 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_8813sadabs
_database_code_depnum_ccdc_archive 'CCDC 1564411'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT03197A 2017
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_block_code                GAA-GA-122-02
_audit_creation_date             2014-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 Title
;
_chemical_formula_moiety         'C32 H42 N3 P, 2(B F4), C2 H3 N'
_chemical_formula_sum            'C34 H45 B2 F8 N4 P'
_chemical_formula_weight         714.33
_chemical_compound_source        dichloromethane,acetonitrile
_chemical_melting_point          ?
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'
B B 0.0013 0.0007 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_symmetry_cell_setting           TRICLINIC
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-p 1'
_symmetry_Int_Tables_number      2

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7253(19)
_cell_length_b                   18.314(3)
_cell_length_c                   20.167(4)
_cell_angle_alpha                113.338(3)
_cell_angle_beta                 90.980(3)
_cell_angle_gamma                93.392(3)
_cell_volume                     3627.2(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9884


_cell_measurement_temperature    100
_cell_measurement_theta_max      28.4863
_cell_measurement_theta_min      2.1835
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.98811
_exptl_absorpt_correction_T_min  0.93860

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0240
0.00 0.00 1.00 0.0420
0.00 1.00 0.00 0.1570
0.00 -1.00 0.00 0.2060
-2.00 -3.00 -1.00 0.1620
1.00 -1.00 0.00 0.1030
-1.00 1.00 0.00 0.1530
-3.00 0.00 -1.00 0.1630

_exptl_crystal_description       plate
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            63233
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.915
_diffrn_reflns_theta_min         1.904
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   1\mS
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11213
_reflns_number_total             15574
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'

_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_refine_diff_density_max         1.644
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     890
_refine_ls_number_reflns         15574
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0829
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1191P)²+8.4221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2185
_refine_ls_wR_factor_ref         0.2454

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.6377 and 1.0000 (SADABS).

Highest peak        ?
Deepest hole        ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F10A(0.5) F10B(0.5) F12A(0.5) F12B(0.5) F2A(0.5) F2B(0.5) F3A(0.5)
 F3B(0.5) N99A(0.5) N99B(0.5) C98A(0.5) C98B(0.5)
3.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C13(H13), C44(H44), C47(H47), C50(H50), C53(H53)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
 C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C57(H57),
  C58(H58), C59(H59), C60(H60), C61(H61), C63(H63), C64(H64), C65(H65),
 C66(H66), C68(H68), C69(H69), C70(H70), C71(H71), C72(H72)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,
 H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C48(H48A,H48B,H48C), C49(H49A,H49B,
 H49C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C55(H55A,
 H55B,H55C), C94(H94A,H94B,H94C), C97(H97A,H97B,H97C)
;
_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
P1 P 0.70741(7) 0.61539(5) 0.77325(4) 0.01717(18) Uani 1 1 d . . . . .
N1 N 0.3800(3) 0.72945(19) 0.79703(18) 0.0301(7) Uani 1 1 d . . . . .
N2 N 0.3810(3) 0.50734(19) 0.71228(18) 0.0299(7) Uani 1 1 d . . . . .
N3 N 0.8351(3) 0.4965(2) 0.6792(2) 0.0402(8) Uani 1 1 d . . . . .
C1 C 0.5451(3) 0.62466(19) 0.77024(18) 0.0194(6) Uani 1 1 d . . . . .
C2 C 0.4377(3) 0.6647(2) 0.77553(19) 0.0238(7) Uani 1 1 d . . . . .
C3 C 0.4332(3) 0.5794(2) 0.74283(19) 0.0237(7) Uani 1 1 d . . . . .
C4 C 0.4452(4) 0.8081(2) 0.8427(2) 0.0352(9) Uani 1 1 d . . . . .
H4 H 0.3797 0.8474 0.8583 0.042 Uiso 1 1 calc R . . . .
C5 C 0.5368(4) 0.8365(2) 0.7996(2) 0.0361(9) Uani 1 1 d . . . . .
H5A H 0.6025 0.7992 0.7829 0.054 Uiso 1 1 calc GR . . . .
H5B H 0.5745 0.8896 0.8303 0.054 Uiso 1 1 calc GR . . . .
H5C H 0.4923 0.8390 0.7578 0.054 Uiso 1 1 calc GR . . . .
C6 C 0.5028(4) 0.8054(3) 0.9110(2) 0.0396(10) Uani 1 1 d . . . . .
H6A H 0.4366 0.7944 0.9394 0.059 Uiso 1 1 calc GR . . . .
H6B H 0.5478 0.8568 0.9398 0.059 Uiso 1 1 calc GR . . . .
H6C H 0.5612 0.7632 0.8980 0.059 Uiso 1 1 calc GR . . . .
C7 C 0.2427(4) 0.7258(3) 0.7794(3) 0.0428(11) Uani 1 1 d . . . . .
H7 H 0.2159 0.6697 0.7463 0.051 Uiso 1 1 calc R . . . .
C8 C 0.2205(4) 0.7787(3) 0.7391(3) 0.0520(12) Uani 1 1 d . . . . .
H8A H 0.2393 0.8347 0.7717 0.078 Uiso 1 1 calc GR . . . .
H8B H 0.1328 0.7707 0.7216 0.078 Uiso 1 1 calc GR . . . .
H8C H 0.2748 0.7649 0.6979 0.078 Uiso 1 1 calc GR . . . .
C9 C 0.1704(4) 0.7463(4) 0.8479(3) 0.0572(14) Uani 1 1 d . . . . .
H9A H 0.1953 0.7133 0.8733 0.086 Uiso 1 1 calc GR . . . .
H9B H 0.0806 0.7360 0.8352 0.086 Uiso 1 1 calc GR . . . .
H9C H 0.1886 0.8027 0.8793 0.086 Uiso 1 1 calc GR . . . .
C10 C 0.2458(3) 0.4875(3) 0.6899(3) 0.0395(10) Uani 1 1 d . . . . .
H10 H 0.2330 0.4281 0.6679 0.047 Uiso 1 1 calc R . . . .
C11 C 0.2133(5) 0.5161(3) 0.6307(3) 0.0556(13) Uani 1 1 d . . . . .
H11A H 0.2307 0.5740 0.6490 0.083 Uiso 1 1 calc GR . . . .
H11B H 0.1244 0.5025 0.6163 0.083 Uiso 1 1 calc GR . . . .
H11C H 0.2638 0.4900 0.5889 0.083 Uiso 1 1 calc GR . . . .
C12 C 0.1642(4) 0.5164(3) 0.7550(3) 0.0501(12) Uani 1 1 d . . . . .
H12A H 0.1866 0.4916 0.7882 0.075 Uiso 1 1 calc GR . . . .
H12B H 0.0762 0.5018 0.7388 0.075 Uiso 1 1 calc GR . . . .
H12C H 0.1773 0.5745 0.7799 0.075 Uiso 1 1 calc GR . . . .
C13 C 0.4588(4) 0.4391(2) 0.7049(3) 0.0370(9) Uani 1 1 d . . . . .
H13 H 0.5461 0.4619 0.7220 0.044 Uiso 1 1 calc R . . . .
C14 C 0.4637(5) 0.3803(3) 0.6270(3) 0.0533(13) Uani 1 1 d . . . . .
H14A H 0.3809 0.3527 0.6100 0.080 Uiso 1 1 calc GR . . . .
H14B H 0.5245 0.3413 0.6237 0.080 Uiso 1 1 calc GR . . . .
H14C H 0.4889 0.4091 0.5969 0.080 Uiso 1 1 calc GR . . . .
C15 C 0.4120(4) 0.3999(3) 0.7545(3) 0.0465(11) Uani 1 1 d . . . . .
H15A H 0.4094 0.4404 0.8039 0.070 Uiso 1 1 calc GR . . . .
H15B H 0.4686 0.3596 0.7539 0.070 Uiso 1 1 calc GR . . . .
H15C H 0.3279 0.3745 0.7377 0.070 Uiso 1 1 calc GR . . . .
C16 C 0.7426(3) 0.57938(18) 0.84161(18) 0.0191(6) Uani 1 1 d . . . . .
C17 C 0.6497(3) 0.5666(2) 0.88384(18) 0.0230(7) Uani 1 1 d . . . . .
H17 H 0.5665 0.5795 0.8790 0.028 Uiso 1 1 calc R . . . .
C18 C 0.6811(4) 0.5344(2) 0.93336(19) 0.0270(7) Uani 1 1 d . . . . .
H18 H 0.6194 0.5252 0.9630 0.032 Uiso 1 1 calc R . . . .
C19 C 0.8033(3) 0.5158(2) 0.9392(2) 0.0276(8) Uani 1 1 d . . . . .
H19 H 0.8251 0.4928 0.9721 0.033 Uiso 1 1 calc R . . . .
C20 C 0.8938(4) 0.5309(2) 0.8968(2) 0.0333(9) Uani 1 1 d . . . . .
H20 H 0.9775 0.5189 0.9018 0.040 Uiso 1 1 calc R . . . .
C21 C 0.8642(3) 0.56260(19) 0.84793(19) 0.0218(7) Uani 1 1 d . . . . .
H21 H 0.9264 0.5728 0.8191 0.026 Uiso 1 1 calc R . . . .
C22 C 0.7396(3) 0.54382(19) 0.68405(18) 0.0218(7) Uani 1 1 d . . . . .
C23 C 0.6692(4) 0.5421(2) 0.6247(2) 0.0292(8) Uani 1 1 d . . . . .
H23 H 0.6023 0.5756 0.6307 0.035 Uiso 1 1 calc R . . . .
C24 C 0.7000(4) 0.4896(3) 0.5562(2) 0.0387(9) Uani 1 1 d . . . . .
H24 H 0.6540 0.4870 0.5145 0.046 Uiso 1 1 calc R . . . .
C25 C 0.7967(4) 0.4419(3) 0.5491(2) 0.0437(11) Uani 1 1 d . . . . .
H25 H 0.8192 0.4067 0.5026 0.052 Uiso 1 1 calc R . . . .
C26 C 0.8617(4) 0.4453(3) 0.6104(3) 0.0462(11) Uani 1 1 d . . . . .
H26 H 0.9272 0.4109 0.6048 0.055 Uiso 1 1 calc R . . . .
C27 C 0.7928(3) 0.70850(19) 0.79087(18) 0.0194(6) Uani 1 1 d . . . . .
C28 C 0.8284(3) 0.7264(2) 0.7326(2) 0.0231(7) Uani 1 1 d . . . . .
H28 H 0.8131 0.6881 0.6845 0.028 Uiso 1 1 calc R . . . .
C29 C 0.8868(3) 0.8011(2) 0.7457(2) 0.0273(8) Uani 1 1 d . . . . .
H29 H 0.9110 0.8140 0.7063 0.033 Uiso 1 1 calc R . . . .
C30 C 0.9095(3) 0.8561(2) 0.8155(2) 0.0309(8) Uani 1 1 d . . . . .
H30 H 0.9497 0.9069 0.8240 0.037 Uiso 1 1 calc R . . . .
C31 C 0.8741(3) 0.8382(2) 0.8734(2) 0.0320(8) Uani 1 1 d . . . . .
H31 H 0.8897 0.8768 0.9214 0.038 Uiso 1 1 calc R . . . .
C32 C 0.8161(3) 0.7642(2) 0.86161(19) 0.0240(7) Uani 1 1 d . . . . .
H32 H 0.7925 0.7516 0.9012 0.029 Uiso 1 1 calc R . . . .
P2 P -0.16980(7) 0.10166(5) 0.76253(4) 0.01653(18) Uani 1 1 d . . . . .
N4 N 0.1915(3) 0.04801(18) 0.69596(15) 0.0227(6) Uani 1 1 d . . . . .
N5 N 0.1292(3) 0.22017(18) 0.86588(16) 0.0277(6) Uani 1 1 d . . . . .
N6 N -0.3405(3) 0.08462(17) 0.84882(16) 0.0235(6) Uani 1 1 d . . . . .
C41 C -0.0043(3) 0.10983(18) 0.76531(17) 0.0186(6) Uani 1 1 d . . . . .
C42 C 0.1164(3) 0.09229(19) 0.74231(17) 0.0191(6) Uani 1 1 d . . . . .
C43 C 0.0960(3) 0.15880(19) 0.80743(18) 0.0198(6) Uani 1 1 d . . . . .
C44 C 0.1436(3) -0.0225(2) 0.63116(19) 0.0263(7) Uani 1 1 d . . . . .
H44 H 0.2180 -0.0476 0.6045 0.032 Uiso 1 1 calc R . . . .
C45 C 0.0664(4) 0.0017(2) 0.5804(2) 0.0336(8) Uani 1 1 d . . . . .
H45A H 0.1156 0.0415 0.5686 0.050 Uiso 1 1 calc GR . . . .
H45B H -0.0096 0.0246 0.6039 0.050 Uiso 1 1 calc GR . . . .
H45C H 0.0435 -0.0452 0.5359 0.050 Uiso 1 1 calc GR . . . .
C46 C 0.0753(4) -0.0838(2) 0.6531(2) 0.0341(8) Uani 1 1 d . . . . .
H46A H 0.0032 -0.0607 0.6810 0.051 Uiso 1 1 calc GR . . . .
H46B H 0.1321 -0.0998 0.6827 0.051 Uiso 1 1 calc GR . . . .
H46C H 0.0466 -0.1306 0.6097 0.051 Uiso 1 1 calc GR . . . .
C47 C 0.3300(3) 0.0665(2) 0.7080(2) 0.0310(8) Uani 1 1 d . . . . .
H47 H 0.3449 0.1142 0.7545 0.037 Uiso 1 1 calc R . . . .
C48 C 0.3847(4) 0.0883(3) 0.6489(3) 0.0440(11) Uani 1 1 d . . . . .
H48A H 0.3374 0.1298 0.6432 0.066 Uiso 1 1 calc GR . . . .
H48B H 0.3799 0.0410 0.6033 0.066 Uiso 1 1 calc GR . . . .
H48C H 0.4723 0.1082 0.6620 0.066 Uiso 1 1 calc GR . . . .
C49 C 0.3924(4) -0.0023(3) 0.7166(2) 0.0395(10) Uani 1 1 d . . . . .
H49A H 0.3857 -0.0489 0.6705 0.059 Uiso 1 1 calc GR . . . .
H49B H 0.3507 -0.0157 0.7536 0.059 Uiso 1 1 calc GR . . . .
H49C H 0.4807 0.0136 0.7313 0.059 Uiso 1 1 calc GR . . . .
C50 C 0.2571(4) 0.2565(3) 0.8895(3) 0.0471(11) Uani 1 1 d . . . . .
H50 H 0.2475 0.3060 0.9337 0.056 Uiso 1 1 calc R . . . .
C51 C 0.3363(4) 0.2064(3) 0.9137(3) 0.0534(12) Uani 1 1 d . . . . .
H51A H 0.3392 0.1536 0.8745 0.080 Uiso 1 1 calc GR . . . .
H51B H 0.3004 0.2008 0.9559 0.080 Uiso 1 1 calc GR . . . .
H51C H 0.4211 0.2320 0.9266 0.080 Uiso 1 1 calc GR . . . .
C52 C 0.3139(5) 0.2846(3) 0.8355(3) 0.0535(12) Uani 1 1 d . . . . .
H52A H 0.2618 0.3236 0.8288 0.080 Uiso 1 1 calc GR . . . .
H52B H 0.3190 0.2391 0.7892 0.080 Uiso 1 1 calc GR . . . .
H52C H 0.3981 0.3095 0.8531 0.080 Uiso 1 1 calc GR . . . .
C53 C 0.0224(4) 0.2632(2) 0.9113(2) 0.0334(8) Uani 1 1 d . . . . .
H53 H -0.0565 0.2296 0.8892 0.040 Uiso 1 1 calc R . . . .
C54 C 0.0354(4) 0.2677(2) 0.9872(2) 0.0402(10) Uani 1 1 d . . . . .
H54A H 0.1072 0.3045 1.0125 0.060 Uiso 1 1 calc GR . . . .
H54B H 0.0483 0.2146 0.9858 0.060 Uiso 1 1 calc GR . . . .
H54C H -0.0407 0.2870 1.0126 0.060 Uiso 1 1 calc GR . . . .
C55 C 0.0100(4) 0.3432(2) 0.9052(3) 0.0430(10) Uani 1 1 d . . . . .
H55A H 0.0015 0.3346 0.8542 0.065 Uiso 1 1 calc GR . . . .
H55B H 0.0847 0.3787 0.9276 0.065 Uiso 1 1 calc GR . . . .
H55C H -0.0640 0.3676 0.9301 0.065 Uiso 1 1 calc GR . . . .
C56 C -0.2152(3) 0.19594(19) 0.76558(18) 0.0199(6) Uani 1 1 d . . . . .
C57 C -0.1645(3) 0.2227(2) 0.71548(19) 0.0248(7) Uani 1 1 d . . . . .
H57 H -0.1126 0.1902 0.6794 0.030 Uiso 1 1 calc R . . . .
C58 C -0.1907(3) 0.2977(2) 0.7189(2) 0.0295(8) Uani 1 1 d . . . . .
H58 H -0.1571 0.3165 0.6848 0.035 Uiso 1 1 calc R . . . .
C59 C -0.2661(3) 0.3450(2) 0.7723(2) 0.0286(8) Uani 1 1 d . . . . .
H59 H -0.2840 0.3960 0.7744 0.034 Uiso 1 1 calc R . . . .
C60 C -0.3153(3) 0.3180(2) 0.8224(2) 0.0278(8) Uani 1 1 d . . . . .
H60 H -0.3656 0.3509 0.8591 0.033 Uiso 1 1 calc R . . . .
C61 C -0.2913(3) 0.2431(2) 0.81902(19) 0.0237(7) Uani 1 1 d . . . . .
H61 H -0.3262 0.2241 0.8527 0.028 Uiso 1 1 calc R . . . .
C62 C -0.2160(3) 0.08624(18) 0.84190(17) 0.0180(6) Uani 1 1 d . . . . .
C63 C -0.1300(3) 0.07362(18) 0.88789(18) 0.0204(6) Uani 1 1 d . . . . .
H63 H -0.0428 0.0753 0.8804 0.024 Uiso 1 1 calc R . . . .
C64 C -0.1770(4) 0.0584(2) 0.94551(19) 0.0274(7) Uani 1 1 d . . . . .
H64 H -0.1221 0.0494 0.9786 0.033 Uiso 1 1 calc R . . . .
C65 C -0.3046(4) 0.0565(2) 0.9538(2) 0.0289(8) Uani 1 1 d . . . . .
H65 H -0.3387 0.0460 0.9925 0.035 Uiso 1 1 calc R . . . .
C66 C -0.3827(3) 0.0702(2) 0.9048(2) 0.0274(7) Uani 1 1 d . . . . .
H66 H -0.4702 0.0693 0.9114 0.033 Uiso 1 1 calc R . . . .
C67 C -0.2382(3) 0.01850(19) 0.68609(17) 0.0190(6) Uani 1 1 d . . . . .
C68 C -0.2578(3) -0.0544(2) 0.6928(2) 0.0273(7) Uani 1 1 d . . . . .
H68 H -0.2322 -0.0593 0.7361 0.033 Uiso 1 1 calc R . . . .
C69 C -0.3144(4) -0.1191(2) 0.6360(2) 0.0326(8) Uani 1 1 d . . . . .
H69 H -0.3284 -0.1687 0.6404 0.039 Uiso 1 1 calc R . . . .
C70 C -0.3511(4) -0.1122(2) 0.5728(2) 0.0337(9) Uani 1 1 d . . . . .
H70 H -0.3884 -0.1574 0.5335 0.040 Uiso 1 1 calc R . . . .
C71 C -0.3335(4) -0.0398(2) 0.5665(2) 0.0331(8) Uani 1 1 d . . . . .
H71 H -0.3599 -0.0352 0.5232 0.040 Uiso 1 1 calc R . . . .
C72 C -0.2773(3) 0.0262(2) 0.62343(19) 0.0263(7) Uani 1 1 d . . . . .
H72 H -0.2658 0.0761 0.6194 0.032 Uiso 1 1 calc R . . . .
F9 F 0.1686(2) 0.02177(18) 0.84027(14) 0.0502(7) Uani 1 1 d . . . . .
F10A F 0.1218(9) 0.0479(6) 0.9529(5) 0.099(3) Uiso 0.5 1 d . . P A 2
F10B F 0.1632(5) 0.0823(3) 0.9603(3) 0.0370(11) Uiso 0.5 1 d . . P A 1
F11 F 0.3256(3) 0.0133(3) 0.9123(2) 0.0837(12) Uani 1 1 d . . . . .
F12A F 0.1252(6) -0.0458(4) 0.9110(3) 0.0503(14) Uiso 0.5 1 d . . P A 1
F12B F 0.1695(6) -0.0674(4) 0.8949(4) 0.0556(16) Uiso 0.5 1 d . . P A 2
B3 B 0.1970(3) 0.0143(2) 0.9024(2) 0.0208(7) Uani 1 1 d . . . . .
F5 F 0.2068(3) 0.5829(2) 0.95264(19) 0.0706(10) Uani 1 1 d . . . . .
F6 F 0.3009(4) 0.7045(2) 1.00633(19) 0.0865(12) Uani 1 1 d . . . . .
F7 F 0.4071(3) 0.6007(3) 0.99907(19) 0.0768(11) Uani 1 1 d . . . . .
F8 F 0.3642(2) 0.62052(16) 0.89699(13) 0.0413(6) Uani 1 1 d . . . . .
B2 B 0.3210(5) 0.6222(4) 0.9618(3) 0.0481(13) Uani 1 1 d . . . . .
F1 F 0.9130(3) 0.68227(17) 0.3546(2) 0.0701(10) Uani 1 1 d . . . . .
F2 F 0.8760(3) 0.7784(2) 0.31361(17) 0.0586(8) Uani 1 1 d . . . . .
F3 F 0.7707(3) 0.7722(2) 0.4073(2) 0.0664(9) Uani 1 1 d . . . . .
F4 F 0.9792(3) 0.80940(18) 0.42035(16) 0.0582(7) Uani 1 1 d . . . . .
B1 B 0.8837(4) 0.7606(3) 0.3737(3) 0.0397(11) Uani 1 1 d . . . . .
F2A F 0.5479(9) 0.2702(6) 0.4331(6) 0.106(3) Uiso 0.5 1 d . . P B 1
F2B F 0.5760(6) 0.2312(4) 0.3840(4) 0.0676(17) Uiso 0.5 1 d . . P B 2
F3A F 0.4578(7) 0.3869(5) 0.4720(4) 0.0745(18) Uiso 0.5 1 d . . P B 1
F3B F 0.4961(9) 0.3362(6) 0.4703(5) 0.104(3) Uiso 0.5 1 d . . P B 2
F57 F 0.4056(4) 0.2892(2) 0.3609(2) 0.0816(11) Uani 1 1 d . . . . .
F70 F 0.5928(4) 0.3574(2) 0.3815(2) 0.0870(11) Uani 1 1 d . . . . .
B5 B 0.5094(3) 0.31810(18) 0.39901(17) 0.0101(6) Uiso 1 1 d . . . . .
N96 N 0.3628(4) 0.8842(3) 0.4821(2) 0.0554(11) Uani 1 1 d . . . . .
C94 C 0.2444(6) 0.7608(3) 0.4887(4) 0.0709(17) Uani 1 1 d . . . . .
H94A H 0.2820 0.7123 0.4571 0.106 Uiso 1 1 calc GR . . . .
H94B H 0.1569 0.7588 0.4728 0.106 Uiso 1 1 calc GR . . . .
H94C H 0.2484 0.7647 0.5386 0.106 Uiso 1 1 calc GR . . . .
C95 C 0.3129(4) 0.8305(3) 0.4850(2) 0.0411(10) Uani 1 1 d . . . . .
N99A N -0.0009(8) 0.3525(6) 0.4173(5) 0.051(2) Uiso 0.5 1 d . . P C 1
N99B N -0.0156(9) 0.3155(6) 0.4208(5) 0.055(2) Uiso 0.5 1 d . . P D 2
C97 C 0.1787(6) 0.3077(3) 0.4828(3) 0.0632(14) Uani 1 1 d . . . . .
H97A H 0.2607 0.3204 0.4677 0.095 Uiso 1 1 calc GR . . E 1
H97B H 0.1668 0.2502 0.4699 0.095 Uiso 1 1 calc GR . . E 1
H97C H 0.1744 0.3361 0.5353 0.095 Uiso 1 1 calc GR . . E 1
C98A C 0.0727(9) 0.3345(6) 0.4436(5) 0.036(2) Uiso 0.5 1 d . . P C 1
C98B C 0.0769(8) 0.3140(6) 0.4503(5) 0.032(2) Uiso 0.5 1 d . . P D 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.762(3) . ?
P1 C16 1.792(3) . ?
P1 C22 1.811(3) . ?
P1 C27 1.788(3) . ?
N1 C2 1.291(5) . ?
N1 C4 1.490(5) . ?
N1 C7 1.500(5) . ?
N2 C3 1.301(5) . ?
N2 C10 1.491(5) . ?
N2 C13 1.503(5) . ?
N3 C22 1.360(5) . ?
N3 C26 1.377(6) . ?
C1 C2 1.384(4) . ?
C1 C3 1.388(5) . ?
C2 C3 1.431(5) . ?
C4 C5 1.524(6) . ?
C4 C6 1.520(6) . ?
C7 C8 1.517(6) . ?
C7 C9 1.520(7) . ?
C10 C11 1.524(6) . ?
C10 C12 1.520(7) . ?
C13 C14 1.517(7) . ?
C13 C15 1.520(6) . ?
C16 C17 1.391(5) . ?
C16 C21 1.372(4) . ?
C17 C18 1.392(5) . ?
C18 C19 1.388(5) . ?
C19 C20 1.390(6) . ?
C20 C21 1.369(5) . ?
C22 C23 1.394(5) . ?
C23 C24 1.393(5) . ?
C24 C25 1.370(7) . ?
C25 C26 1.386(7) . ?
C27 C28 1.393(5) . ?
C27 C32 1.394(5) . ?
C28 C29 1.393(5) . ?
C29 C30 1.375(6) . ?
C30 C31 1.386(6) . ?
C31 C32 1.386(5) . ?
P2 C41 1.771(3) . ?
P2 C56 1.800(3) . ?
P2 C62 1.804(3) . ?
P2 C67 1.790(3) . ?
N4 C42 1.297(4) . ?
N4 C44 1.483(5) . ?
N4 C47 1.498(4) . ?
N5 C43 1.292(4) . ?
N5 C50 1.472(5) . ?
N5 C53 1.531(5) . ?
N6 C62 1.345(4) . ?
N6 C66 1.337(5) . ?
C41 C42 1.395(4) . ?
C41 C43 1.391(5) . ?
C42 C43 1.425(5) . ?
C44 C45 1.518(5) . ?
C44 C46 1.517(5) . ?
C47 C48 1.515(6) . ?
C47 C49 1.527(5) . ?
C50 C51 1.494(7) . ?
C50 C52 1.501(7) . ?
C53 C54 1.503(6) . ?
C53 C55 1.530(5) . ?
C56 C57 1.391(5) . ?
C56 C61 1.396(5) . ?
C57 C58 1.394(5) . ?
C58 C59 1.392(5) . ?
C59 C60 1.389(5) . ?
C60 C61 1.385(5) . ?
C62 C63 1.389(5) . ?
C63 C64 1.394(5) . ?
C64 C65 1.382(5) . ?
C65 C66 1.390(5) . ?
C67 C68 1.398(5) . ?
C67 C72 1.387(5) . ?
C68 C69 1.378(5) . ?
C69 C70 1.384(6) . ?
C70 C71 1.384(6) . ?
C71 C72 1.391(5) . ?
F9 B3 1.345(4) . ?
F10A B3 1.288(10) . ?
F10B B3 1.400(6) . ?
F11 B3 1.393(5) . ?
F12A B3 1.375(7) . ?
F12B B3 1.455(7) . ?
F5 B2 1.355(6) . ?
F6 B2 1.448(7) . ?
F7 B2 1.351(6) . ?
F8 B2 1.384(5) . ?
F1 B1 1.387(5) . ?
F2 B1 1.377(6) . ?
F3 B1 1.385(6) . ?
F4 B1 1.388(6) . ?
F2A B5 1.387(10) . ?
F2B B5 1.702(7) . ?
F3A B5 1.643(8) . ?
F3B B5 1.354(10) . ?
F57 B5 1.301(5) . ?
F70 B5 1.256(5) . ?
N96 C95 1.115(6) . ?
C94 C95 1.463(7) . ?
N99A C98A 1.081(13) . ?
N99B C98B 1.154(13) . ?
C97 C98A 1.582(12) . ?
C97 C98B 1.299(11) . ?

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
C1 P1 C16 108.33(15) . . ?
C1 P1 C22 104.82(16) . . ?
C1 P1 C27 111.05(15) . . ?
C16 P1 C22 111.58(15) . . ?
C27 P1 C16 111.10(15) . . ?
C27 P1 C22 109.79(15) . . ?
C2 N1 C4 121.4(3) . . ?
C2 N1 C7 119.9(3) . . ?
C4 N1 C7 118.6(3) . . ?
C3 N2 C10 124.5(3) . . ?
C3 N2 C13 118.2(3) . . ?
C10 N2 C13 117.1(3) . . ?
C22 N3 C26 116.1(4) . . ?
C2 C1 P1 155.7(3) . . ?
C2 C1 C3 62.2(3) . . ?
C3 C1 P1 141.2(3) . . ?
N1 C2 C1 151.4(4) . . ?
N1 C2 C3 149.4(3) . . ?
C1 C2 C3 59.1(2) . . ?
N2 C3 C1 144.8(3) . . ?
N2 C3 C2 156.4(3) . . ?
C1 C3 C2 58.8(2) . . ?
N1 C4 C5 111.5(3) . . ?
N1 C4 C6 110.3(3) . . ?
C6 C4 C5 114.2(4) . . ?
N1 C7 C8 109.3(3) . . ?
N1 C7 C9 109.9(4) . . ?
C8 C7 C9 114.0(4) . . ?
N2 C10 C11 110.1(3) . . ?
N2 C10 C12 111.3(4) . . ?
C12 C10 C11 115.0(4) . . ?
N2 C13 C14 112.2(4) . . ?
N2 C13 C15 109.6(3) . . ?
C14 C13 C15 112.8(4) . . ?
C17 C16 P1 121.1(2) . . ?
C21 C16 P1 116.5(3) . . ?
C21 C16 C17 122.3(3) . . ?
C16 C17 C18 118.6(3) . . ?
C19 C18 C17 119.5(3) . . ?
C18 C19 C20 120.0(3) . . ?
C21 C20 C19 121.1(3) . . ?
C20 C21 C16 118.5(3) . . ?
N3 C22 P1 117.2(3) . . ?
N3 C22 C23 123.9(3) . . ?
C23 C22 P1 118.8(3) . . ?
C24 C23 C22 117.9(4) . . ?
C25 C24 C23 119.8(4) . . ?
C24 C25 C26 119.5(4) . . ?
N3 C26 C25 122.7(4) . . ?
C28 C27 P1 118.8(3) . . ?
C28 C27 C32 120.6(3) . . ?
C32 C27 P1 120.5(3) . . ?
C29 C28 C27 119.3(3) . . ?
C30 C29 C28 120.1(3) . . ?
C29 C30 C31 120.6(3) . . ?
C30 C31 C32 120.3(3) . . ?
C31 C32 C27 119.1(3) . . ?
C41 P2 C56 104.97(15) . . ?
C41 P2 C62 107.00(15) . . ?
C41 P2 C67 113.78(14) . . ?
C56 P2 C62 111.30(15) . . ?
C67 P2 C56 112.96(15) . . ?
C67 P2 C62 106.75(15) . . ?
C42 N4 C44 121.4(3) . . ?
C42 N4 C47 120.1(3) . . ?
C44 N4 C47 118.4(3) . . ?
C43 N5 C50 126.8(3) . . ?
C43 N5 C53 115.7(3) . . ?
C50 N5 C53 117.3(3) . . ?
C66 N6 C62 116.5(3) . . ?
C42 C41 P2 158.2(3) . . ?
C43 C41 P2 140.2(3) . . ?
C43 C41 C42 61.5(2) . . ?
N4 C42 C41 150.4(3) . . ?
N4 C42 C43 150.5(3) . . ?
C41 C42 C43 59.1(2) . . ?
N5 C43 C41 145.4(3) . . ?
N5 C43 C42 155.2(3) . . ?
C41 C43 C42 59.4(2) . . ?
N4 C44 C45 111.3(3) . . ?
N4 C44 C46 110.6(3) . . ?
C46 C44 C45 113.6(3) . . ?
N4 C47 C48 111.2(3) . . ?
N4 C47 C49 110.4(3) . . ?
C48 C47 C49 112.9(3) . . ?
N5 C50 C51 112.8(4) . . ?
N5 C50 C52 111.4(4) . . ?
C51 C50 C52 115.4(4) . . ?
C54 C53 N5 111.0(3) . . ?
C54 C53 C55 115.1(3) . . ?
C55 C53 N5 110.1(3) . . ?
C57 C56 P2 117.2(2) . . ?
C57 C56 C61 121.1(3) . . ?
C61 C56 P2 121.5(3) . . ?
C56 C57 C58 119.1(3) . . ?
C59 C58 C57 119.9(3) . . ?
C60 C59 C58 120.4(3) . . ?
C61 C60 C59 120.2(3) . . ?
C60 C61 C56 119.2(3) . . ?
N6 C62 P2 112.8(2) . . ?
N6 C62 C63 124.9(3) . . ?
C63 C62 P2 122.2(2) . . ?
C62 C63 C64 117.2(3) . . ?
C65 C64 C63 118.9(3) . . ?
C64 C65 C66 119.4(3) . . ?
N6 C66 C65 123.1(3) . . ?
C68 C67 P2 117.7(3) . . ?
C72 C67 P2 121.7(3) . . ?
C72 C67 C68 120.4(3) . . ?
C69 C68 C67 119.5(3) . . ?
C68 C69 C70 120.3(4) . . ?
C69 C70 C71 120.3(4) . . ?
C70 C71 C72 120.1(4) . . ?
C67 C72 C71 119.4(3) . . ?
F9 B3 F10B 108.7(3) . . ?
F9 B3 F11 111.1(3) . . ?
F9 B3 F12A 112.9(4) . . ?
F9 B3 F12B 110.7(4) . . ?
F10A B3 F9 113.5(5) . . ?
F10A B3 F11 125.3(6) . . ?
F10A B3 F12B 97.8(6) . . ?
F11 B3 F10B 105.1(4) . . ?
F11 B3 F12B 94.7(4) . . ?
F12A B3 F10B 102.5(4) . . ?
F12A B3 F11 115.8(4) . . ?
F5 B2 F6 104.8(4) . . ?
F5 B2 F8 111.5(5) . . ?
F7 B2 F5 115.0(5) . . ?
F7 B2 F6 105.6(5) . . ?
F7 B2 F8 112.3(4) . . ?
F8 B2 F6 106.9(4) . . ?
F1 B1 F4 107.5(4) . . ?
F2 B1 F1 110.6(4) . . ?
F2 B1 F3 109.5(4) . . ?
F2 B1 F4 108.9(3) . . ?
F3 B1 F1 109.7(3) . . ?
F3 B1 F4 110.5(4) . . ?
F2A B5 F3A 95.5(5) . . ?
F3B B5 F2B 94.1(5) . . ?
F57 B5 F2A 111.9(5) . . ?
F57 B5 F2B 99.0(3) . . ?
F57 B5 F3A 100.9(4) . . ?
F57 B5 F3B 112.6(5) . . ?
F70 B5 F2A 117.4(5) . . ?
F70 B5 F2B 102.8(4) . . ?
F70 B5 F3A 101.7(4) . . ?
F70 B5 F3B 117.9(5) . . ?
F70 B5 F57 122.6(4) . . ?
N96 C95 C94 178.5(6) . . ?
N99A C98A C97 179.0(11) . . ?
N99B C98B C97 176.3(12) . . ?




_shelxl_version_number           2014-3
####################################################################### 
# 
# 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_8326sadabs
_database_code_depnum_ccdc_archive 'CCDC 1564417'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT03197A 2017
_audit_update_record             
;
2017-10-29 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT410_8326sadabs          
;
PROBLEM: Short Intra H...H Contact   H47    ..  H53A    .       1.69 Ang.  
RESPONSE: H53 is the hydrogen atom attached to a tertiary carbon atom 
          of the minor component of the disordered 
          bis-isopropylamino substituent in close proximity to H47, the 
          hydrogen atom attached to a tertiary carbon atom of the other
          amino substituent, which was not treated as being disordered. 
;
_audit_block_code                HOS-HH-111-03
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelx_SHELXL_version_number     2017/1
_chemical_compound_source        dichloromethane,pentane
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C H2 Cl2), 2(C33 H43 N2 P), 4(B F4)'
_chemical_formula_sum            'C68 H90 B4 Cl4 F16 N4 P2'
_chemical_formula_weight         1514.41
_chemical_melting_point          ?
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'
B B 0.0013 0.0007 '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'
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'

_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_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                   18.675(3)
_cell_length_b                   15.547(3)
_cell_length_c                   25.725(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.330(3)
_cell_angle_gamma                90
_cell_volume                     7437(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9770
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.79
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.99053
_exptl_absorpt_correction_T_min  0.97150
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.9037.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3152
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            208223
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.498
_diffrn_reflns_theta_min         1.292
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'CCD φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                15874
_reflns_number_total             22623
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_refine_diff_density_max         1.626
_refine_diff_density_min         -1.239
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     982
_refine_ls_number_reflns         22623
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0727
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+14.2381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.2013
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl4C-C99C = Cl4A-C99A = Cl3C-C99C = Cl3A-C99A
 1.74 with sigma of 0.001
3. Others
 Sof(C50B)=Sof(H50B)=Sof(C51B)=Sof(H51D)=Sof(H51E)=Sof(H51F)=Sof(C52B)=
 Sof(H52D)=Sof(H52E)=Sof(H52F)=Sof(C53A)=Sof(H53A)=Sof(C54A)=Sof(H54A)=
 Sof(H54B)=Sof(H54C)=Sof(C55A)=Sof(H55A)=Sof(H55B)=Sof(H55C)=1-FVAR(1)
 Sof(C50A)=Sof(H50A)=Sof(C51A)=Sof(H51A)=Sof(H51B)=Sof(H51C)=Sof(C52A)=
 Sof(H52A)=Sof(H52B)=Sof(H52C)=Sof(C53B)=Sof(H53B)=Sof(C54B)=Sof(H54D)=
 Sof(H54E)=Sof(H54F)=Sof(C55B)=Sof(H55D)=Sof(H55E)=Sof(H55F)=FVAR(1)
 Fixed Sof: Cl3A(0.33333) Cl3B(0.33333) Cl3C(0.33333) Cl4A(0.33333)
 Cl4B(0.33333) Cl4C(0.33333) F6A(0.33333) F6B(0.33333) F6C(0.33333)
 F7A(0.33333) F7B(0.33333) F7C(0.33333) F8A(0.33333) F8B(0.33333) F8C(0.33333)
 F9A(0.5) F9B(0.5) F10A(0.5) F10B(0.5) F12A(0.5) F12B(0.5) F13A(0.33333)
 F13B(0.33333) F13C(0.33333) F14A(0.33333) F14B(0.33333) F14C(0.33333)
 F15A(0.33333) F15B(0.33333) F15C(0.33333) C99A(0.33333) H99A(0.33333)
 H99B(0.33333) C99B(0.33333) H99C(0.33333) H99D(0.33333) C99C(0.33333)
 H99E(0.33333) H99F(0.33333)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C13(H13), C44(H44), C47(H47), C50A(H50A),
 C50B(H50B), C53A(H53A), C53B(H53B)
4.b Secondary CH2 refined with riding coordinates:
 C98(H98A,H98B), C99A(H99A,H99B), C99B(H99C,H99D), C99C(H99E,H99F)
4.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
 C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
  C57(H57), C58(H58), C59(H59), C60(H60), C61(H61), C63(H63), C64(H64),
 C65(H65), C66(H66), C67(H67), C69(H69), C70(H70), C71(H71), C72(H72), C73(H73)
4.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,
 H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C48(H48A,H48B,H48C), C49(H49A,H49B,
 H49C), C51A(H51A,H51B,H51C), C51B(H51D,H51E,H51F), C52A(H52A,H52B,H52C),
 C52B(H52D,H52E,H52F), C54A(H54A,H54B,H54C), C54B(H54D,H54E,H54F), C55A(H55A,
 H55B,H55C), C55B(H55D,H55E,H55F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.48482(4) 0.51524(5) 0.56493(3) 0.03635(16) Uani 1 1 d . . . . .
Cl2 Cl 0.55533(6) 0.63238(7) 0.64171(3) 0.0596(3) Uani 1 1 d . . . . .
Cl3A Cl -0.0184(2) 0.5590(3) 0.58733(19) 0.0448(13) Uiso 0.3333 1 d D . P A 1
Cl3B Cl -0.0123(2) 0.5463(3) 0.58897(17) 0.0390(11) Uiso 0.3333 1 d . . P B 2
Cl3C Cl 0.0137(2) 0.5531(3) 0.56733(16) 0.0710(9) Uiso 0.3333 1 d D . P C 3
Cl4A Cl 0.09821(15) 0.6595(2) 0.64737(12) 0.0345(7) Uiso 0.3333 1 d D . P A 1
Cl4B Cl 0.0651(3) 0.6615(4) 0.6558(2) 0.0878(13) Uiso 0.3333 1 d . . P B 2
Cl4C Cl 0.0923(2) 0.6419(2) 0.65466(15) 0.0456(9) Uiso 0.3333 1 d D . P C 3
P1 P 0.25771(3) 0.90939(4) 0.33018(2) 0.01621(11) Uani 1 1 d . . . . .
P2 P 0.23536(3) 0.11930(4) 0.66939(2) 0.02023(12) Uani 1 1 d . . . . .
F1 F 0.61845(9) 0.65793(13) 0.35497(7) 0.0412(4) Uani 1 1 d . . . . .
F2 F 0.55602(9) 0.67576(12) 0.27528(7) 0.0377(4) Uani 1 1 d . . . . .
F3 F 0.67658(9) 0.65568(13) 0.28197(8) 0.0426(4) Uani 1 1 d . . . . .
F4 F 0.60257(12) 0.54422(12) 0.29833(8) 0.0487(5) Uani 1 1 d . . . . .
F5 F 0.33095(11) 0.80430(12) 0.49095(7) 0.0445(5) Uani 1 1 d . . . . .
F6A F 0.4424(4) 0.8031(5) 0.5130(3) 0.0681(19) Uiso 0.3333 1 d . . P D 1
F6B F 0.4314(4) 0.7590(5) 0.5457(3) 0.0479(17) Uiso 0.3333 1 d . . P D 2
F6C F 0.4120(3) 0.7565(4) 0.5587(2) 0.0319(12) Uiso 0.3333 1 d . . P D 3
F7A F 0.3692(4) 0.7393(4) 0.5657(3) 0.0524(15) Uiso 0.3333 1 d . . P D 1
F7B F 0.3350(6) 0.8299(7) 0.5772(4) 0.070(3) Uiso 0.3333 1 d . . P D 2
F7C F 0.3268(4) 0.8534(5) 0.5719(3) 0.0401(16) Uiso 0.3333 1 d . . P D 3
F8A F 0.3726(4) 0.8814(5) 0.5644(3) 0.0664(19) Uiso 0.3333 1 d . . P D 1
F8B F 0.4242(3) 0.8916(4) 0.5225(3) 0.0359(14) Uiso 0.3333 1 d . . P D 2
F8C F 0.4096(3) 0.9017(3) 0.5337(2) 0.0260(11) Uiso 0.3333 1 d . . P D 3
F9A F 0.1052(3) 0.2491(4) 0.4350(2) 0.0651(15) Uiso 0.5 1 d . . P E 1
F9B F 0.1108(2) 0.2159(3) 0.43098(16) 0.0386(9) Uiso 0.5 1 d . . P E 2
F10A F 0.1148(4) 0.1180(4) 0.4696(3) 0.0869(17) Uiso 0.5 1 d . . P E 1
F10B F 0.0737(2) 0.1027(2) 0.47724(15) 0.0393(8) Uiso 0.5 1 d . . P E 2
F11 F 0.12755(13) 0.22231(16) 0.52101(8) 0.0619(6) Uani 1 1 d . . . . .
F12A F 0.0173(2) 0.2297(3) 0.48068(17) 0.0382(9) Uiso 0.5 1 d . . P E 1
F12B F 0.0169(4) 0.1995(5) 0.4796(3) 0.078(2) Uiso 0.5 1 d . . P E 2
F13A F 0.5592(5) 0.8288(6) 0.7472(4) 0.081(2) Uiso 0.3333 1 d . . P F 1
F13B F 0.5893(3) 0.7799(4) 0.7477(2) 0.0312(12) Uiso 0.3333 1 d . . P F 2
F13C F 0.5913(4) 0.7704(5) 0.7664(3) 0.0511(19) Uiso 0.3333 1 d . . P F 3
F14A F 0.6130(4) 0.7879(5) 0.8221(3) 0.059(2) Uiso 0.3333 1 d . . P F 1
F14B F 0.6112(3) 0.8121(5) 0.8367(2) 0.0218(10) Uiso 0.3333 1 d . . P F 2
F14C F 0.6104(4) 0.8398(5) 0.8444(3) 0.048(2) Uiso 0.3333 1 d . . P F 3
F15A F 0.5745(4) 0.9304(5) 0.8079(4) 0.067(2) Uiso 0.3333 1 d . . P F 1
F15B F 0.5637(3) 0.9173(3) 0.7823(3) 0.0202(11) Uiso 0.3333 1 d . . P F 2
F15C F 0.5620(3) 0.9044(4) 0.7682(3) 0.0308(15) Uiso 0.3333 1 d . . P F 3
F16 F 0.67817(9) 0.87251(12) 0.77633(8) 0.0397(4) Uani 1 1 d . . . . .
N1 N 0.32229(10) 0.67885(13) 0.37833(8) 0.0212(4) Uani 1 1 d . . . . .
N2 N 0.16529(11) 0.76653(13) 0.44001(8) 0.0214(4) Uani 1 1 d . . . . .
N3 N 0.31029(11) 0.22025(14) 0.54093(8) 0.0242(4) Uani 1 1 d . . . . .
N4 N 0.20057(11) 0.36312(14) 0.61647(9) 0.0265(4) Uani 1 1 d . . . . .
C1 C 0.24729(11) 0.81776(14) 0.36959(9) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.27336(11) 0.73683(14) 0.38374(9) 0.0182(4) Uani 1 1 d . . . . .
C3 C 0.21307(12) 0.77187(14) 0.40680(9) 0.0189(4) Uani 1 1 d . . . . .
C4 C 0.38157(13) 0.70224(18) 0.34530(10) 0.0272(5) Uani 1 1 d . . . . .
H4 H 0.369111 0.759832 0.329676 0.033 Uiso 1 1 calc R . . . .
C5 C 0.38551(16) 0.6403(2) 0.30031(12) 0.0397(7) Uani 1 1 d . . . . .
H5A H 0.403532 0.584621 0.313678 0.060 Uiso 1 1 calc GR . . . .
H5B H 0.418111 0.663354 0.275997 0.060 Uiso 1 1 calc GR . . . .
H5C H 0.337451 0.632924 0.282083 0.060 Uiso 1 1 calc GR . . . .
C6 C 0.45219(14) 0.71298(19) 0.37899(12) 0.0334(6) Uani 1 1 d . . . . .
H6A H 0.445695 0.753776 0.407213 0.050 Uiso 1 1 calc GR . . . .
H6B H 0.488918 0.734867 0.357559 0.050 Uiso 1 1 calc GR . . . .
H6C H 0.467526 0.657243 0.393935 0.050 Uiso 1 1 calc GR . . . .
C7 C 0.32578(15) 0.59343(16) 0.40458(11) 0.0290(5) Uani 1 1 d . . . . .
H7 H 0.367668 0.562868 0.391496 0.035 Uiso 1 1 calc R . . . .
C8 C 0.34275(15) 0.60095(18) 0.46329(11) 0.0326(6) Uani 1 1 d . . . . .
H8A H 0.389341 0.629463 0.470920 0.049 Uiso 1 1 calc GR . . . .
H8B H 0.344651 0.543390 0.478895 0.049 Uiso 1 1 calc GR . . . .
H8C H 0.305207 0.634836 0.477949 0.049 Uiso 1 1 calc GR . . . .
C9 C 0.26024(17) 0.54032(18) 0.38660(13) 0.0384(7) Uani 1 1 d . . . . .
H9A H 0.216751 0.570811 0.394795 0.058 Uiso 1 1 calc GR . . . .
H9B H 0.262936 0.484646 0.404537 0.058 Uiso 1 1 calc GR . . . .
H9C H 0.258565 0.531109 0.348821 0.058 Uiso 1 1 calc GR . . . .
C10 C 0.15820(14) 0.68783(17) 0.47208(11) 0.0282(5) Uani 1 1 d . . . . .
H10 H 0.194606 0.645336 0.461930 0.034 Uiso 1 1 calc R . . . .
C11 C 0.17579(17) 0.7081(2) 0.52973(12) 0.0384(7) Uani 1 1 d . . . . .
H11A H 0.223885 0.733605 0.535101 0.058 Uiso 1 1 calc GR . . . .
H11B H 0.174530 0.654920 0.550105 0.058 Uiso 1 1 calc GR . . . .
H11C H 0.140284 0.748704 0.541096 0.058 Uiso 1 1 calc GR . . . .
C12 C 0.08399(17) 0.6477(2) 0.45954(14) 0.0401(7) Uani 1 1 d . . . . .
H12A H 0.046974 0.688214 0.468714 0.060 Uiso 1 1 calc GR . . . .
H12B H 0.080669 0.594595 0.479689 0.060 Uiso 1 1 calc GR . . . .
H12C H 0.076695 0.634567 0.422165 0.060 Uiso 1 1 calc GR . . . .
C13 C 0.11721(13) 0.84125(16) 0.44844(10) 0.0251(5) Uani 1 1 d . . . . .
H13 H 0.089327 0.826373 0.478561 0.030 Uiso 1 1 calc R . . . .
C14 C 0.06304(14) 0.85485(17) 0.40119(12) 0.0301(5) Uani 1 1 d . . . . .
H14A H 0.088666 0.864629 0.370163 0.045 Uiso 1 1 calc GR . . . .
H14B H 0.033020 0.904958 0.407132 0.045 Uiso 1 1 calc GR . . . .
H14C H 0.032553 0.803714 0.395870 0.045 Uiso 1 1 calc GR . . . .
C15 C 0.16307(15) 0.91926(17) 0.46446(11) 0.0290(5) Uani 1 1 d . . . . .
H15A H 0.192047 0.907163 0.497380 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.131829 0.968797 0.469069 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.194898 0.932127 0.437255 0.043 Uiso 1 1 calc GR . . . .
C16 C 0.17366(11) 0.96450(15) 0.31771(9) 0.0184(4) Uani 1 1 d . . . . .
C17 C 0.15775(13) 1.03551(15) 0.34789(9) 0.0216(4) Uani 1 1 d . . . . .
H17 H 0.192383 1.057029 0.374060 0.026 Uiso 1 1 calc R . . . .
C18 C 0.09036(14) 1.07445(17) 0.33914(10) 0.0274(5) Uani 1 1 d . . . . .
H18 H 0.078947 1.122801 0.359395 0.033 Uiso 1 1 calc R . . . .
C19 C 0.04000(14) 1.04258(19) 0.30086(10) 0.0303(6) Uani 1 1 d . . . . .
H19 H -0.005829 1.069227 0.295096 0.036 Uiso 1 1 calc R . . . .
C20 C 0.05604(13) 0.97231(19) 0.27106(10) 0.0282(5) Uani 1 1 d . . . . .
H20 H 0.021129 0.951001 0.245012 0.034 Uiso 1 1 calc R . . . .
C21 C 0.12282(12) 0.93268(16) 0.27894(9) 0.0224(4) Uani 1 1 d . . . . .
H21 H 0.133906 0.884636 0.258328 0.027 Uiso 1 1 calc R . . . .
C22 C 0.28683(12) 0.87177(15) 0.26942(9) 0.0201(4) Uani 1 1 d . . . . .
C23 C 0.25764(15) 0.79649(18) 0.24680(11) 0.0305(5) Uani 1 1 d . . . . .
H23 H 0.224483 0.763241 0.264201 0.037 Uiso 1 1 calc R . . . .
C24 C 0.27764(17) 0.7708(2) 0.19859(12) 0.0392(7) Uani 1 1 d . . . . .
H24 H 0.257903 0.719595 0.183024 0.047 Uiso 1 1 calc R . . . .
C25 C 0.32587(16) 0.8186(2) 0.17281(11) 0.0362(6) Uani 1 1 d . . . . .
H25 H 0.339226 0.800040 0.139865 0.043 Uiso 1 1 calc R . . . .
C26 C 0.35468(16) 0.8936(2) 0.19521(11) 0.0341(6) Uani 1 1 d . . . . .
H26 H 0.387519 0.926737 0.177459 0.041 Uiso 1 1 calc R . . . .
C27 C 0.33555(14) 0.92028(16) 0.24364(10) 0.0252(5) Uani 1 1 d . . . . .
H27 H 0.355590 0.971395 0.259130 0.030 Uiso 1 1 calc R . . . .
C28 C 0.32394(12) 0.97981(16) 0.36212(9) 0.0207(4) Uani 1 1 d . . . . .
C29 C 0.33438(14) 1.06011(17) 0.33976(11) 0.0272(5) Uani 1 1 d . . . . .
H29 H 0.304149 1.078214 0.310035 0.033 Uiso 1 1 calc R . . . .
C30 C 0.38931(16) 1.1137(2) 0.36119(13) 0.0371(7) Uani 1 1 d . . . . .
H30 H 0.397200 1.168023 0.345797 0.044 Uiso 1 1 calc R . . . .
C31 C 0.43221(15) 1.0873(2) 0.40495(13) 0.0420(8) Uani 1 1 d . . . . .
H31 H 0.469706 1.123679 0.419524 0.050 Uiso 1 1 calc R . . . .
C32 C 0.42118(14) 1.0088(2) 0.42764(12) 0.0387(7) Uani 1 1 d . . . . .
H32 H 0.450842 0.991963 0.457941 0.046 Uiso 1 1 calc R . . . .
C33 C 0.36671(13) 0.95327(19) 0.40664(10) 0.0279(5) Uani 1 1 d . . . . .
H33 H 0.359135 0.899086 0.422296 0.034 Uiso 1 1 calc R . . . .
C41 C 0.24090(12) 0.20401(15) 0.62347(9) 0.0204(4) Uani 1 1 d . . . . .
C42 C 0.27213(11) 0.23362(14) 0.57997(9) 0.0182(4) Uani 1 1 d . . . . .
C43 C 0.22949(11) 0.28919(15) 0.60863(9) 0.0188(4) Uani 1 1 d . . . . .
C44 C 0.34229(16) 0.1365(2) 0.52923(13) 0.0382(7) Uani 1 1 d . . . . .
H44 H 0.357383 0.142945 0.493142 0.046 Uiso 1 1 calc R . . . .
C45 C 0.28794(16) 0.06652(19) 0.52506(16) 0.0441(8) Uani 1 1 d . . . . .
H45A H 0.273392 0.053290 0.559808 0.066 Uiso 1 1 calc GR . . . .
H45B H 0.308728 0.015072 0.510381 0.066 Uiso 1 1 calc GR . . . .
H45C H 0.245821 0.085025 0.502226 0.066 Uiso 1 1 calc GR . . . .
C46 C 0.41049(14) 0.1171(2) 0.56272(13) 0.0373(7) Uani 1 1 d . . . . .
H46A H 0.448651 0.155831 0.553407 0.056 Uiso 1 1 calc GR . . . .
H46B H 0.424706 0.057349 0.557099 0.056 Uiso 1 1 calc GR . . . .
H46C H 0.402641 0.125301 0.599534 0.056 Uiso 1 1 calc GR . . . .
C47 C 0.32355(16) 0.2934(2) 0.50401(11) 0.0343(6) Uani 1 1 d . . . . .
H47 H 0.298349 0.344339 0.517537 0.041 Uiso 1 1 calc R . . . .
C48 C 0.28862(18) 0.2785(2) 0.45027(13) 0.0462(8) Uani 1 1 d . . . . .
H48A H 0.312340 0.230375 0.434223 0.069 Uiso 1 1 calc GR . . . .
H48B H 0.292896 0.330463 0.429214 0.069 Uiso 1 1 calc GR . . . .
H48C H 0.237672 0.264871 0.452049 0.069 Uiso 1 1 calc GR . . . .
C49 C 0.40164(18) 0.3174(2) 0.50778(15) 0.0477(9) Uani 1 1 d . . . . .
H49A H 0.418395 0.329888 0.544240 0.072 Uiso 1 1 calc GR . . . .
H49B H 0.407994 0.368523 0.486370 0.072 Uiso 1 1 calc GR . . . .
H49C H 0.429545 0.269618 0.495209 0.072 Uiso 1 1 calc GR . . . .
C50A C 0.1565(2) 0.3628(3) 0.6652(2) 0.0280(10) Uani 0.670(9) 1 d . . P G 2
H50A H 0.172907 0.312219 0.687184 0.034 Uiso 0.670(9) 1 calc R . P G 2
C50B C 0.1428(4) 0.3916(6) 0.6437(4) 0.0235(18) Uani 0.330(9) 1 d . . P G 1
H50B H 0.128098 0.450111 0.630585 0.028 Uiso 0.330(9) 1 calc R . P G 1
C51A C 0.0772(4) 0.3499(5) 0.6479(3) 0.0389(14) Uani 0.670(9) 1 d . . P G 2
H51A H 0.059449 0.398647 0.626155 0.058 Uiso 0.670(9) 1 calc GR . P G 2
H51B H 0.050063 0.346254 0.678639 0.058 Uiso 0.670(9) 1 calc GR . P G 2
H51C H 0.070798 0.296616 0.627640 0.058 Uiso 0.670(9) 1 calc GR . P G 2
C51B C 0.0808(7) 0.3294(9) 0.6296(5) 0.031(2) Uani 0.330(9) 1 d . . P G 1
H51D H 0.068956 0.329430 0.591649 0.047 Uiso 0.330(9) 1 calc GR . P G 1
H51E H 0.038704 0.347562 0.646808 0.047 Uiso 0.330(9) 1 calc GR . P G 1
H51F H 0.095042 0.271326 0.641172 0.047 Uiso 0.330(9) 1 calc GR . P G 1
C52A C 0.1718(3) 0.4427(5) 0.6978(2) 0.0425(14) Uani 0.670(9) 1 d . . P G 2
H52A H 0.223877 0.451263 0.703828 0.064 Uiso 0.670(9) 1 calc GR . P G 2
H52B H 0.151483 0.436035 0.731308 0.064 Uiso 0.670(9) 1 calc GR . P G 2
H52C H 0.149871 0.492629 0.679249 0.064 Uiso 0.670(9) 1 calc GR . P G 2
C52B C 0.1663(6) 0.3979(8) 0.7008(4) 0.032(2) Uani 0.330(9) 1 d . . P G 1
H52D H 0.185957 0.342403 0.713414 0.048 Uiso 0.330(9) 1 calc GR . P G 1
H52E H 0.125036 0.412986 0.719861 0.048 Uiso 0.330(9) 1 calc GR . P G 1
H52F H 0.203439 0.442321 0.706595 0.048 Uiso 0.330(9) 1 calc GR . P G 1
C53A C 0.2324(6) 0.4393(5) 0.5784(4) 0.027(2) Uani 0.330(9) 1 d . . P G 1
H53A H 0.274997 0.414996 0.562687 0.032 Uiso 0.330(9) 1 calc R . P G 1
C53B C 0.1981(3) 0.4369(3) 0.58417(18) 0.0271(10) Uani 0.670(9) 1 d . . P G 2
H53B H 0.165022 0.478239 0.599621 0.033 Uiso 0.670(9) 1 calc R . P G 2
C54A C 0.1745(6) 0.4606(8) 0.5337(4) 0.035(2) Uani 0.330(9) 1 d . . P G 1
H54A H 0.158230 0.407349 0.515961 0.052 Uiso 0.330(9) 1 calc GR . P G 1
H54B H 0.194878 0.499112 0.508796 0.052 Uiso 0.330(9) 1 calc GR . P G 1
H54C H 0.133712 0.488774 0.547988 0.052 Uiso 0.330(9) 1 calc GR . P G 1
C54B C 0.1645(3) 0.4180(4) 0.52936(19) 0.0349(11) Uani 0.670(9) 1 d . . P G 2
H54D H 0.191726 0.372381 0.513800 0.052 Uiso 0.670(9) 1 calc GR . P G 2
H54E H 0.165408 0.470164 0.508027 0.052 Uiso 0.670(9) 1 calc GR . P G 2
H54F H 0.114599 0.399362 0.530876 0.052 Uiso 0.670(9) 1 calc GR . P G 2
C55A C 0.2570(6) 0.5171(6) 0.6103(5) 0.042(3) Uani 0.330(9) 1 d . . P G 1
H55A H 0.216623 0.540384 0.627582 0.063 Uiso 0.330(9) 1 calc GR . P G 1
H55B H 0.274698 0.560999 0.587309 0.063 Uiso 0.330(9) 1 calc GR . P G 1
H55C H 0.295795 0.500500 0.636697 0.063 Uiso 0.330(9) 1 calc GR . P G 1
C55B C 0.2712(2) 0.4799(3) 0.5882(2) 0.0334(11) Uani 0.670(9) 1 d . . P G 2
H55D H 0.284324 0.497805 0.624328 0.050 Uiso 0.670(9) 1 calc GR . P G 2
H55E H 0.269427 0.530497 0.565326 0.050 Uiso 0.670(9) 1 calc GR . P G 2
H55F H 0.307209 0.439363 0.577405 0.050 Uiso 0.670(9) 1 calc GR . P G 2
C56 C 0.19795(13) 0.15992(16) 0.72669(10) 0.0246(5) Uani 1 1 d . . . . .
C57 C 0.12242(15) 0.16643(18) 0.72465(12) 0.0330(6) Uani 1 1 d . . . . .
H57 H 0.093326 0.146436 0.694841 0.040 Uiso 1 1 calc R . . . .
C58 C 0.09066(17) 0.2022(2) 0.76640(14) 0.0391(7) Uani 1 1 d . . . . .
H58 H 0.039870 0.208077 0.764842 0.047 Uiso 1 1 calc R . . . .
C59 C 0.13334(18) 0.22923(19) 0.81029(13) 0.0395(7) Uani 1 1 d . . . . .
H59 H 0.111498 0.253513 0.838801 0.047 Uiso 1 1 calc R . . . .
C60 C 0.20709(18) 0.2213(2) 0.81308(12) 0.0389(7) Uani 1 1 d . . . . .
H60 H 0.235650 0.239128 0.843663 0.047 Uiso 1 1 calc R . . . .
C61 C 0.23989(16) 0.1872(2) 0.77114(11) 0.0330(6) Uani 1 1 d . . . . .
H61 H 0.290783 0.182631 0.772916 0.040 Uiso 1 1 calc R . . . .
C62 C 0.17658(12) 0.03621(16) 0.64332(10) 0.0226(4) Uani 1 1 d . . . . .
C63 C 0.17201(14) -0.03828(17) 0.67352(11) 0.0267(5) Uani 1 1 d . . . . .
H63 H 0.199684 -0.043288 0.706279 0.032 Uiso 1 1 calc R . . . .
C64 C 0.12685(14) -0.10459(18) 0.65527(11) 0.0299(5) Uani 1 1 d . . . . .
H64 H 0.124282 -0.155833 0.675126 0.036 Uiso 1 1 calc R . . . .
C65 C 0.08539(14) -0.09596(18) 0.60791(11) 0.0308(6) Uani 1 1 d . . . . .
H65 H 0.054712 -0.141684 0.595420 0.037 Uiso 1 1 calc R . . . .
C66 C 0.08824(13) -0.02123(19) 0.57858(11) 0.0292(5) Uani 1 1 d . . . . .
H66 H 0.058628 -0.015500 0.546685 0.035 Uiso 1 1 calc R . . . .
C67 C 0.13457(12) 0.04553(17) 0.59587(10) 0.0239(5) Uani 1 1 d . . . . .
H67 H 0.137438 0.096377 0.575690 0.029 Uiso 1 1 calc R . . . .
C68 C 0.32548(12) 0.07945(16) 0.68204(9) 0.0222(4) Uani 1 1 d . . . . .
C69 C 0.37890(13) 0.13588(18) 0.70337(10) 0.0268(5) Uani 1 1 d . . . . .
H69 H 0.366866 0.192968 0.712447 0.032 Uiso 1 1 calc R . . . .
C70 C 0.44978(14) 0.1074(2) 0.71112(11) 0.0333(6) Uani 1 1 d . . . . .
H70 H 0.486201 0.144991 0.726029 0.040 Uiso 1 1 calc R . . . .
C71 C 0.46734(14) 0.0248(2) 0.69725(12) 0.0348(6) Uani 1 1 d . . . . .
H71 H 0.515719 0.005681 0.703178 0.042 Uiso 1 1 calc R . . . .
C72 C 0.41516(15) -0.03030(19) 0.67478(12) 0.0339(6) Uani 1 1 d . . . . .
H72 H 0.428075 -0.086491 0.664550 0.041 Uiso 1 1 calc R . . . .
C73 C 0.34377(14) -0.00368(17) 0.66712(11) 0.0281(5) Uani 1 1 d . . . . .
H73 H 0.307810 -0.041588 0.651913 0.034 Uiso 1 1 calc R . . . .
C98 C 0.47248(17) 0.5882(2) 0.61548(12) 0.0366(6) Uani 1 1 d . . . . .
H98A H 0.449242 0.558343 0.643458 0.044 Uiso 1 1 calc R . . . .
H98B H 0.440164 0.635148 0.601861 0.044 Uiso 1 1 calc R . . . .
C99A C 0.0095(3) 0.6527(5) 0.6202(5) 0.052(4) Uiso 0.3333 1 d D . P A 1
H99A H 0.000877 0.701315 0.595531 0.063 Uiso 0.3333 1 calc R . P A 1
H99B H -0.021985 0.661646 0.648617 0.063 Uiso 0.3333 1 calc R . P A 1
C99B C 0.0154(4) 0.6525(5) 0.6054(4) 0.0247(18) Uiso 0.3333 1 d . . P B 2
H99C H 0.040277 0.676435 0.576320 0.030 Uiso 0.3333 1 calc R . P B 2
H99D H -0.028039 0.687995 0.608650 0.030 Uiso 0.3333 1 calc R . P B 2
C99C C 0.0090(3) 0.6085(11) 0.6257(4) 0.087(5) Uiso 0.3333 1 d D . P C 3
H99E H -0.022160 0.659570 0.619004 0.104 Uiso 0.3333 1 calc R . P C 3
H99F H -0.013857 0.570919 0.650472 0.104 Uiso 0.3333 1 calc R . P C 3
B1 B 0.61254(16) 0.6324(2) 0.30285(12) 0.0283(6) Uani 1 1 d . . . . .
B2 B 0.37680(19) 0.8195(2) 0.53531(13) 0.0363(7) Uani 1 1 d . . . . .
B3 B 0.08671(17) 0.1937(2) 0.47728(12) 0.0292(6) Uani 1 1 d . . . . .
B4 B 0.60877(17) 0.8484(2) 0.78772(14) 0.0347(7) 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
Cl1 C98 1.757(3) . ?
Cl2 C98 1.768(3) . ?
Cl3A C99A 1.7405(10) . ?
Cl3B C99B 1.770(9) . ?
Cl3C C99C 1.7404(11) . ?
Cl4A C99A 1.7400(11) . ?
Cl4B C99B 1.529(10) . ?
Cl4C C99C 1.7406(11) . ?
P1 C1 1.770(2) . ?
P1 C16 1.791(2) . ?
P1 C22 1.800(2) . ?
P1 C28 1.793(2) . ?
P2 C41 1.779(2) . ?
P2 C56 1.803(3) . ?
P2 C62 1.785(2) . ?
P2 C68 1.795(2) . ?
F1 B1 1.393(3) . ?
F2 B1 1.390(3) . ?
F3 B1 1.403(3) . ?
F4 B1 1.387(4) . ?
F5 B2 1.382(4) . ?
F6A B2 1.423(9) . ?
F6B B2 1.395(8) . ?
F6C B2 1.296(7) . ?
F7A B2 1.484(8) . ?
F7B B2 1.398(11) . ?
F7C B2 1.484(8) . ?
F8A B2 1.227(8) . ?
F8B B2 1.484(7) . ?
F8C B2 1.420(6) . ?
F9A B3 1.453(7) . ?
F9B B3 1.356(5) . ?
F10A B3 1.312(7) . ?
F10B B3 1.436(5) . ?
F11 B3 1.373(3) . ?
F12A B3 1.422(5) . ?
F12B B3 1.313(8) . ?
F13A B4 1.363(10) . ?
F13B B4 1.502(7) . ?
F13C B4 1.358(8) . ?
F14A B4 1.289(8) . ?
F14B B4 1.377(6) . ?
F14C B4 1.462(8) . ?
F15A B4 1.538(9) . ?
F15B B4 1.361(6) . ?
F15C B4 1.300(7) . ?
F16 B4 1.406(4) . ?
N1 C2 1.300(3) . ?
N1 C4 1.501(3) . ?
N1 C7 1.489(3) . ?
N2 C3 1.294(3) . ?
N2 C10 1.489(3) . ?
N2 C13 1.496(3) . ?
N3 C42 1.301(3) . ?
N3 C44 1.475(3) . ?
N3 C47 1.517(4) . ?
N4 C43 1.294(3) . ?
N4 C50A 1.561(5) . ?
N4 C50B 1.410(8) . ?
N4 C53A 1.679(9) . ?
N4 C53B 1.414(5) . ?
C1 C2 1.386(3) . ?
C1 C3 1.395(3) . ?
C2 C3 1.428(3) . ?
C4 C5 1.512(4) . ?
C4 C6 1.519(4) . ?
C7 C8 1.519(4) . ?
C7 C9 1.513(4) . ?
C10 C11 1.522(4) . ?
C10 C12 1.527(4) . ?
C13 C14 1.522(4) . ?
C13 C15 1.519(4) . ?
C16 C17 1.397(3) . ?
C16 C21 1.402(3) . ?
C17 C18 1.396(3) . ?
C18 C19 1.388(4) . ?
C19 C20 1.383(4) . ?
C20 C21 1.389(3) . ?
C22 C23 1.395(3) . ?
C22 C27 1.396(3) . ?
C23 C24 1.387(4) . ?
C24 C25 1.383(5) . ?
C25 C26 1.387(4) . ?
C26 C27 1.391(4) . ?
C28 C29 1.396(4) . ?
C28 C33 1.396(3) . ?
C29 C30 1.395(4) . ?
C30 C31 1.382(5) . ?
C31 C32 1.377(5) . ?
C32 C33 1.403(4) . ?
C41 C42 1.388(3) . ?
C41 C43 1.389(3) . ?
C42 C43 1.426(3) . ?
C44 C45 1.485(4) . ?
C44 C46 1.501(4) . ?
C47 C48 1.491(4) . ?
C47 C49 1.500(4) . ?
C50A C51A 1.521(8) . ?
C50A C52A 1.511(7) . ?
C50B C51B 1.526(15) . ?
C50B C52B 1.498(13) . ?
C53A C54A 1.539(14) . ?
C53A C55A 1.510(14) . ?
C53B C54B 1.518(6) . ?
C53B C55B 1.515(7) . ?
C56 C57 1.410(4) . ?
C56 C61 1.391(4) . ?
C57 C58 1.390(4) . ?
C58 C59 1.385(5) . ?
C59 C60 1.378(5) . ?
C60 C61 1.394(4) . ?
C62 C63 1.401(3) . ?
C62 C67 1.396(3) . ?
C63 C64 1.386(4) . ?
C64 C65 1.388(4) . ?
C65 C66 1.389(4) . ?
C66 C67 1.397(4) . ?
C68 C69 1.401(3) . ?
C68 C73 1.399(4) . ?
C69 C70 1.392(4) . ?
C70 C71 1.380(4) . ?
C71 C72 1.383(4) . ?
C72 C73 1.392(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
C1 P1 C16 110.28(10) . . ?
C1 P1 C22 107.10(11) . . ?
C1 P1 C28 109.69(11) . . ?
C16 P1 C22 109.29(11) . . ?
C16 P1 C28 110.23(11) . . ?
C28 P1 C22 110.20(11) . . ?
C41 P2 C56 109.54(12) . . ?
C41 P2 C62 110.98(11) . . ?
C41 P2 C68 105.34(11) . . ?
C62 P2 C56 106.81(11) . . ?
C62 P2 C68 110.60(12) . . ?
C68 P2 C56 113.63(12) . . ?
C2 N1 C4 117.1(2) . . ?
C2 N1 C7 124.9(2) . . ?
C7 N1 C4 118.0(2) . . ?
C3 N2 C10 121.4(2) . . ?
C3 N2 C13 120.4(2) . . ?
C10 N2 C13 118.18(19) . . ?
C42 N3 C44 124.0(2) . . ?
C42 N3 C47 119.8(2) . . ?
C44 N3 C47 116.2(2) . . ?
C43 N4 C50A 112.4(3) . . ?
C43 N4 C50B 134.9(5) . . ?
C43 N4 C53A 111.1(4) . . ?
C43 N4 C53B 128.3(3) . . ?
C50B N4 C53A 113.3(5) . . ?
C53B N4 C50A 118.9(3) . . ?
C2 C1 P1 145.79(18) . . ?
C2 C1 C3 61.80(16) . . ?
C3 C1 P1 152.41(18) . . ?
N1 C2 C1 146.6(2) . . ?
N1 C2 C3 153.9(2) . . ?
C1 C2 C3 59.44(16) . . ?
N2 C3 C1 150.9(2) . . ?
N2 C3 C2 150.2(2) . . ?
C1 C3 C2 58.76(15) . . ?
N1 C4 C5 111.7(2) . . ?
N1 C4 C6 110.5(2) . . ?
C5 C4 C6 113.9(2) . . ?
N1 C7 C8 112.3(2) . . ?
N1 C7 C9 110.4(2) . . ?
C9 C7 C8 115.7(3) . . ?
N2 C10 C11 110.4(2) . . ?
N2 C10 C12 110.1(2) . . ?
C11 C10 C12 113.6(2) . . ?
N2 C13 C14 110.8(2) . . ?
N2 C13 C15 109.2(2) . . ?
C15 C13 C14 114.9(2) . . ?
C17 C16 P1 120.43(17) . . ?
C17 C16 C21 120.6(2) . . ?
C21 C16 P1 118.89(18) . . ?
C18 C17 C16 119.2(2) . . ?
C19 C18 C17 120.1(2) . . ?
C20 C19 C18 120.5(2) . . ?
C19 C20 C21 120.5(2) . . ?
C20 C21 C16 119.1(2) . . ?
C23 C22 P1 119.81(19) . . ?
C23 C22 C27 120.1(2) . . ?
C27 C22 P1 119.99(18) . . ?
C24 C23 C22 119.2(3) . . ?
C25 C24 C23 121.0(3) . . ?
C24 C25 C26 119.8(3) . . ?
C25 C26 C27 120.1(3) . . ?
C26 C27 C22 119.8(2) . . ?
C29 C28 P1 118.30(19) . . ?
C29 C28 C33 120.7(2) . . ?
C33 C28 P1 120.9(2) . . ?
C30 C29 C28 119.8(3) . . ?
C31 C30 C29 119.6(3) . . ?
C32 C31 C30 120.7(3) . . ?
C31 C32 C33 120.9(3) . . ?
C28 C33 C32 118.2(3) . . ?
C42 C41 P2 146.72(19) . . ?
C42 C41 C43 61.80(16) . . ?
C43 C41 P2 150.6(2) . . ?
N3 C42 C41 150.6(2) . . ?
N3 C42 C43 150.2(2) . . ?
C41 C42 C43 59.15(16) . . ?
N4 C43 C41 149.3(2) . . ?
N4 C43 C42 151.7(2) . . ?
C41 C43 C42 59.05(16) . . ?
N3 C44 C45 112.0(2) . . ?
N3 C44 C46 113.5(2) . . ?
C45 C44 C46 115.6(3) . . ?
C48 C47 N3 112.4(2) . . ?
C48 C47 C49 116.0(3) . . ?
C49 C47 N3 111.1(2) . . ?
C51A C50A N4 109.7(4) . . ?
C52A C50A N4 110.9(4) . . ?
C52A C50A C51A 113.5(5) . . ?
N4 C50B C51B 106.4(7) . . ?
N4 C50B C52B 109.8(8) . . ?
C52B C50B C51B 114.9(9) . . ?
C54A C53A N4 109.0(7) . . ?
C55A C53A N4 110.8(8) . . ?
C55A C53A C54A 113.0(8) . . ?
N4 C53B C54B 112.2(4) . . ?
N4 C53B C55B 109.8(4) . . ?
C55B C53B C54B 116.2(5) . . ?
C57 C56 P2 117.2(2) . . ?
C61 C56 P2 123.2(2) . . ?
C61 C56 C57 119.6(3) . . ?
C58 C57 C56 119.8(3) . . ?
C59 C58 C57 119.8(3) . . ?
C60 C59 C58 120.8(3) . . ?
C59 C60 C61 120.2(3) . . ?
C56 C61 C60 119.9(3) . . ?
C63 C62 P2 117.18(19) . . ?
C67 C62 P2 121.97(19) . . ?
C67 C62 C63 120.8(2) . . ?
C64 C63 C62 119.6(3) . . ?
C63 C64 C65 119.9(3) . . ?
C64 C65 C66 120.7(2) . . ?
C65 C66 C67 120.1(3) . . ?
C62 C67 C66 118.8(2) . . ?
C69 C68 P2 118.4(2) . . ?
C73 C68 P2 121.18(19) . . ?
C73 C68 C69 120.2(2) . . ?
C70 C69 C68 119.3(3) . . ?
C71 C70 C69 120.3(3) . . ?
C70 C71 C72 120.6(3) . . ?
C71 C72 C73 120.2(3) . . ?
C72 C73 C68 119.4(3) . . ?
Cl1 C98 Cl2 111.28(17) . . ?
Cl4A C99A Cl3A 118.5(3) . . ?
Cl4B C99B Cl3B 115.4(6) . . ?
Cl4C C99C Cl3C 113.7(3) . . ?
F1 B1 F3 107.5(2) . . ?
F2 B1 F1 110.0(2) . . ?
F2 B1 F3 108.3(2) . . ?
F4 B1 F1 111.1(3) . . ?
F4 B1 F2 110.3(2) . . ?
F4 B1 F3 109.6(2) . . ?
F5 B2 F6A 97.3(4) . . ?
F5 B2 F6B 115.4(4) . . ?
F5 B2 F7A 102.0(4) . . ?
F5 B2 F7B 108.0(5) . . ?
F5 B2 F7C 101.9(4) . . ?
F5 B2 F8B 106.4(3) . . ?
F5 B2 F8C 111.4(3) . . ?
F6A B2 F7A 101.0(5) . . ?
F6B B2 F7B 112.4(6) . . ?
F6B B2 F8B 96.4(4) . . ?
F6C B2 F5 120.2(4) . . ?
F6C B2 F7C 107.3(5) . . ?
F6C B2 F8C 119.5(4) . . ?
F7B B2 F8B 118.1(6) . . ?
F8A B2 F5 124.7(5) . . ?
F8A B2 F6A 119.5(6) . . ?
F8A B2 F7A 108.8(5) . . ?
F8C B2 F7C 89.8(4) . . ?
F9B B3 F10B 108.6(3) . . ?
F9B B3 F11 115.7(3) . . ?
F10A B3 F9A 107.0(4) . . ?
F10A B3 F11 102.4(4) . . ?
F10A B3 F12A 138.0(4) . . ?
F11 B3 F9A 105.6(3) . . ?
F11 B3 F10B 113.6(3) . . ?
F11 B3 F12A 105.2(3) . . ?
F12A B3 F9A 95.4(3) . . ?
F12B B3 F9B 115.7(4) . . ?
F12B B3 F10B 84.2(4) . . ?
F12B B3 F11 114.8(4) . . ?
F13A B4 F15A 99.7(6) . . ?
F13A B4 F16 118.3(5) . . ?
F13C B4 F14C 107.6(5) . . ?
F13C B4 F16 110.2(4) . . ?
F14A B4 F13A 110.9(6) . . ?
F14A B4 F15A 111.9(6) . . ?
F14A B4 F16 109.8(4) . . ?
F14B B4 F13B 108.8(5) . . ?
F14B B4 F16 110.3(3) . . ?
F15B B4 F13B 112.3(4) . . ?
F15B B4 F14B 112.6(5) . . ?
F15B B4 F16 110.0(3) . . ?
F15C B4 F13C 108.4(5) . . ?
F15C B4 F14C 113.4(5) . . ?
F15C B4 F16 109.9(3) . . ?
F16 B4 F13B 102.4(3) . . ?
F16 B4 F14C 107.4(4) . . ?
F16 B4 F15A 105.7(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
