# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

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

data_test1
_database_code_depnum_ccdc_archive 'CCDC 1967513'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2020-04-04 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
(Fluoromethyl)trimethylphosphonium iodide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H11 F I P'
_chemical_formula_sum            'C4 H11 F I P'
_chemical_formula_weight         236.00

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   12.1430(5)
_cell_length_b                   7.3397(3)
_cell_length_c                   9.2655(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     825.80(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    2382
_cell_measurement_theta_min      4.8560
_cell_measurement_theta_max      31.8860

_exptl_crystal_description       neadle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            8368
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.356
_diffrn_reflns_theta_max         30.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1346
_reflns_number_gt                1124
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0189P)²+0.0931P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1346
_refine_ls_number_parameters     43
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0504
_refine_ls_wR_factor_gt          0.0460
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_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
I1 I 0.59772(2) 0.250000 0.12587(2) 0.02987(8) Uani 1 2 d S T P . .
P1 P 0.28456(6) 0.750000 0.32796(9) 0.02236(16) Uani 1 2 d S T P . .
C1 C 0.1838(3) 0.750000 0.1901(4) 0.0342(8) Uani 1 2 d S T P A .
H1A H 0.220139 0.750000 0.095695 0.051 Uiso 1 2 calc R U P . .
H1B H 0.137727 0.640981 0.199177 0.051 Uiso 0.5 1 calc R U P . .
H1C H 0.137727 0.859019 0.199178 0.051 Uiso 0.5 1 calc R U P . .
C2 C 0.2200(3) 0.750000 0.4994(4) 0.0340(7) Uani 1 2 d S T P A .
H2A H 0.276366 0.750000 0.575144 0.051 Uiso 1 2 calc R U P . .
H2B H 0.174008 0.859019 0.508972 0.051 Uiso 0.5 1 calc R U P . .
H2C H 0.174008 0.640981 0.508972 0.051 Uiso 0.5 1 calc R U P . .
C3 C 0.37011(19) 0.5523(3) 0.3102(3) 0.0326(5) Uani 0.5 1 d . . P A 1
H3A H 0.324098 0.440991 0.310738 0.039 Uiso 0.5 1 calc R U P A 1
H3B H 0.410728 0.556982 0.217586 0.039 Uiso 0.5 1 calc R U P A 1
F1 F 0.4429(2) 0.5480(5) 0.4230(4) 0.0463(8) Uani 0.5 1 d . . P A 1
C3B C 0.37011(19) 0.5523(3) 0.3102(3) 0.0326(5) Uani 0.5 1 d . . P A 2
H3BA H 0.425902 0.552494 0.386577 0.049 Uiso 0.5 1 calc R U P A 2
H3BB H 0.324725 0.442422 0.318406 0.049 Uiso 0.5 1 calc R U P A 2
H3BC H 0.406481 0.554004 0.215747 0.049 Uiso 0.5 1 calc R 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
P1 C1 1.768(3) . ?
P1 C2 1.771(3) . ?
P1 C3B 1.792(2) . ?
P1 C3 1.792(2) . ?
P1 C3 1.792(2) 8_575 ?
C3 F1 1.370(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 C2 109.97(17) . . ?
C1 P1 C3B 109.55(11) . . ?
C2 P1 C3B 109.82(11) . . ?
C1 P1 C3 109.55(11) . . ?
C2 P1 C3 109.82(11) . . ?
C1 P1 C3 109.55(11) . 8_575 ?
C2 P1 C3 109.82(11) . 8_575 ?
C3B P1 C3 108.12(16) . 8_575 ?
C3 P1 C3 108.12(16) . 8_575 ?
F1 C3 P1 108.8(2) . . ?

_refine_diff_density_max         1.020
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_test1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1967516'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2020-04-04 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
Tris(diethylamino)fluoromethylphosphonium iodide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H32 F N3 P, I'
_chemical_formula_sum            'C13 H32 F I N3 P'
_chemical_formula_weight         407.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   10.0648(3)
_cell_length_b                   10.1439(5)
_cell_length_c                   18.6453(8)
_cell_angle_alpha                93.292(4)
_cell_angle_beta                 92.580(3)
_cell_angle_gamma                90.104(3)
_cell_volume                     1898.53(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5313
_cell_measurement_theta_min      4.3250
_cell_measurement_theta_max      24.4380

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.774
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96762
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            30663
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.151
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9397
_reflns_number_gt                6203
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9397
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
I1 I 0.74200(2) 0.27915(3) 0.02648(2) 0.04177(9) Uani 1 1 d . . . . .
I2 I 0.70646(3) 0.23337(3) 0.46723(2) 0.04840(9) Uani 1 1 d . . . . .
P1 P 0.27964(8) 0.27768(9) 0.09112(5) 0.0278(2) Uani 1 1 d . . . . .
P2 P 0.28039(9) 0.23888(9) 0.59876(5) 0.0307(2) Uani 1 1 d . . . . .
N5 N 0.2377(3) 0.2499(3) 0.51509(15) 0.0319(7) Uani 1 1 d . . . . .
N3 N 0.2521(2) 0.2168(3) 0.01000(15) 0.0291(7) Uani 1 1 d . . . . .
F2 F 0.4698(2) 0.1061(3) 0.66968(13) 0.0660(7) Uani 1 1 d . . . . .
N6 N 0.3361(3) 0.3757(3) 0.63730(16) 0.0354(7) Uani 1 1 d . . . . .
F1 F 0.4188(2) 0.4832(3) 0.15129(13) 0.0609(7) Uani 1 1 d . . . . .
N2 N 0.1478(3) 0.3417(3) 0.12552(15) 0.0305(7) Uani 1 1 d . . . . .
N1 N 0.3422(3) 0.1640(3) 0.13992(16) 0.0328(7) Uani 1 1 d . . . . .
C19 C 0.2910(4) 0.0994(5) 0.4100(2) 0.0553(12) Uani 1 1 d . . . . .
H19A H 0.3823 0.0941 0.4302 0.083 Uiso 1 1 calc R U . . .
H19B H 0.2855 0.1695 0.3759 0.083 Uiso 1 1 calc R U . . .
H19C H 0.2658 0.0148 0.3849 0.083 Uiso 1 1 calc R U . . .
C13 C 0.3981(3) 0.4128(4) 0.0863(2) 0.0335(9) Uani 1 1 d . . . . .
H13A H 0.484(2) 0.3766(9) 0.0706(4) 0.040 Uiso 1 1 calc R U . . .
H13B H 0.3646(8) 0.4732(14) 0.0499(9) 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0587(3) 0.2632(4) 0.1676(2) 0.0405(10) Uani 1 1 d . . . . .
H5A H 0.0797(5) 0.168(2) 0.1593(3) 0.049 Uiso 1 1 calc R U . . .
H5B H -0.034(2) 0.2765(5) 0.1502(5) 0.049 Uiso 1 1 calc R U . . .
C7 C 0.0946(3) 0.4678(4) 0.1013(2) 0.0371(9) Uani 1 1 d . . . . .
H7A H 0.010(2) 0.4551(5) 0.0853(5) 0.044 Uiso 1 1 calc R U . . .
H7B H 0.1409(11) 0.4918(7) 0.0642(10) 0.044 Uiso 1 1 calc R U . . .
N4 N 0.1559(3) 0.1845(3) 0.64039(15) 0.0353(7) Uani 1 1 d . . . . .
C11 C 0.3660(3) 0.1729(4) -0.03333(19) 0.0352(9) Uani 1 1 d . . . . .
H11A H 0.3504(5) 0.084(2) -0.0517(5) 0.042 Uiso 1 1 calc R U . . .
H11B H 0.4449(19) 0.1735(4) -0.0027(8) 0.042 Uiso 1 1 calc R U . . .
C16 C 0.0173(3) 0.1818(4) 0.6103(2) 0.0410(10) Uani 1 1 d . . . . .
H16A H -0.0079(7) 0.092(2) 0.5984(4) 0.049 Uiso 1 1 calc R U . . .
H16B H 0.0139(3) 0.2272(12) 0.5669(12) 0.049 Uiso 1 1 calc R U . . .
C2 C 0.5580(4) 0.1569(5) 0.2110(3) 0.0696(15) Uani 1 1 d . . . . .
H2A H 0.6054 0.2002 0.1739 0.104 Uiso 1 1 calc R U . . .
H2B H 0.5622 0.0609 0.2020 0.104 Uiso 1 1 calc R U . . .
H2C H 0.5996 0.1816 0.2584 0.104 Uiso 1 1 calc R U . . .
C26 C 0.4169(4) 0.1226(4) 0.6004(2) 0.0401(9) Uani 1 1 d . . . . .
H26A H 0.3867(8) 0.040(2) 0.5800(6) 0.048 Uiso 1 1 calc R U . . .
H26B H 0.4847(17) 0.1525(8) 0.5719(8) 0.048 Uiso 1 1 calc R U . . .
C9 C 0.1214(3) 0.2231(4) -0.0296(2) 0.0396(10) Uani 1 1 d . . . . .
H9A H 0.1237(3) 0.2939(18) -0.0627(8) 0.048 Uiso 1 1 calc R U . . .
H9B H 0.0531(17) 0.2446(7) 0.0046(8) 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2808(4) -0.0605(4) 0.1770(2) 0.0539(12) Uani 1 1 d . . . . .
H4A H 0.1962 -0.0242 0.1930 0.081 Uiso 1 1 calc R U . . .
H4B H 0.3458 -0.0589 0.2178 0.081 Uiso 1 1 calc R U . . .
H4C H 0.2670 -0.1517 0.1578 0.081 Uiso 1 1 calc R U . . .
C15 C 0.1347(4) -0.0112(4) 0.7132(3) 0.0599(13) Uani 1 1 d . . . . .
H15A H 0.1789 -0.0629 0.6753 0.090 Uiso 1 1 calc R U . . .
H15B H 0.0381 -0.0178 0.7047 0.090 Uiso 1 1 calc R U . . .
H15C H 0.1597 -0.0454 0.7600 0.090 Uiso 1 1 calc R U . . .
C22 C 0.2459(4) 0.4738(4) 0.6713(2) 0.0449(10) Uani 1 1 d . . . . .
H22A H 0.2545 0.5584 0.6479 0.054 Uiso 1 1 calc R U . . .
H22B H 0.1530 0.4426 0.6626 0.054 Uiso 1 1 calc R U . . .
C8 C 0.0991(4) 0.5792(4) 0.1583(2) 0.0554(12) Uani 1 1 d . . . . .
H8A H 0.1885 0.5856 0.1813 0.083 Uiso 1 1 calc R U . . .
H8B H 0.0345 0.5623 0.1945 0.083 Uiso 1 1 calc R U . . .
H8C H 0.0772 0.6622 0.1362 0.083 Uiso 1 1 calc R U . . .
C6 C 0.0705(4) 0.2993(5) 0.2473(2) 0.0581(12) Uani 1 1 d . . . . .
H6A H 0.0521 0.3935 0.2559 0.087 Uiso 1 1 calc R U . . .
H6B H 0.1608 0.2802 0.2657 0.087 Uiso 1 1 calc R U . . .
H6C H 0.0063 0.2474 0.2721 0.087 Uiso 1 1 calc R U . . .
C14 C 0.1771(4) 0.1317(4) 0.7127(2) 0.0470(11) Uani 1 1 d . . . . .
H14A H 0.1287(12) 0.1820(14) 0.7459(9) 0.056 Uiso 1 1 calc R U . . .
H14B H 0.267(2) 0.1391(5) 0.7270(5) 0.056 Uiso 1 1 calc R U . . .
C17 C -0.0826(4) 0.2433(5) 0.6604(2) 0.0527(11) Uani 1 1 d . . . . .
H17A H -0.0559 0.3343 0.6745 0.079 Uiso 1 1 calc R U . . .
H17B H -0.0861 0.1922 0.7033 0.079 Uiso 1 1 calc R U . . .
H17C H -0.1707 0.2431 0.6357 0.079 Uiso 1 1 calc R U . . .
C3 C 0.3321(4) 0.0220(4) 0.1188(2) 0.0430(10) Uani 1 1 d . . . . .
H3A H 0.418(2) -0.0093(9) 0.1065(4) 0.052 Uiso 1 1 calc R U . . .
H3B H 0.2745(14) 0.0104(5) 0.0772(11) 0.052 Uiso 1 1 calc R U . . .
C18 C 0.1979(4) 0.1298(4) 0.4696(2) 0.0420(10) Uani 1 1 d . . . . .
H18A H 0.107(2) 0.1423(4) 0.4486(5) 0.050 Uiso 1 1 calc R U . . .
H18B H 0.1953(4) 0.0537(19) 0.5002(8) 0.050 Uiso 1 1 calc R U . . .
C20 C 0.2419(4) 0.3752(4) 0.4777(2) 0.0478(10) Uani 1 1 d . . . . .
H20A H 0.3128 0.3693 0.4426 0.057 Uiso 1 1 calc R U . . .
H20B H 0.2652 0.4486 0.5135 0.057 Uiso 1 1 calc R U . . .
C1 C 0.4153(4) 0.2000(4) 0.2089(2) 0.0490(11) Uani 1 1 d . . . . .
H1A H 0.3689(13) 0.1590(11) 0.2487(11) 0.059 Uiso 1 1 calc R U . . .
H1B H 0.4121(4) 0.298(3) 0.2180(4) 0.059 Uiso 1 1 calc R U . . .
C24 C 0.4682(4) 0.4281(4) 0.6175(2) 0.0435(10) Uani 1 1 d . . . . .
H24A H 0.4955(8) 0.3795(13) 0.5761(12) 0.052 Uiso 1 1 calc R U . . .
H24B H 0.4575(4) 0.517(2) 0.6056(4) 0.052 Uiso 1 1 calc R U . . .
C10 C 0.0845(4) 0.0957(4) -0.0713(2) 0.0492(11) Uani 1 1 d . . . . .
H10A H 0.0936 0.0223 -0.0395 0.074 Uiso 1 1 calc R U . . .
H10B H 0.1436 0.0816 -0.1113 0.074 Uiso 1 1 calc R U . . .
H10C H -0.0078 0.1004 -0.0901 0.074 Uiso 1 1 calc R U . . .
C12 C 0.3888(4) 0.2580(4) -0.0953(2) 0.0511(11) Uani 1 1 d . . . . .
H12A H 0.3999 0.3502 -0.0773 0.077 Uiso 1 1 calc R U . . .
H12B H 0.3122 0.2505 -0.1296 0.077 Uiso 1 1 calc R U . . .
H12C H 0.4691 0.2286 -0.1192 0.077 Uiso 1 1 calc R U . . .
C21 C 0.1130(4) 0.4062(5) 0.4393(2) 0.0644(13) Uani 1 1 d . . . . .
H21A H 0.0413 0.4067 0.4731 0.097 Uiso 1 1 calc R U . . .
H21B H 0.0942 0.3391 0.4002 0.097 Uiso 1 1 calc R U . . .
H21C H 0.1191 0.4932 0.4193 0.097 Uiso 1 1 calc R U . . .
C25 C 0.5747(4) 0.4222(6) 0.6749(3) 0.0716(16) Uani 1 1 d . . . . .
H25A H 0.5837 0.3312 0.6894 0.107 Uiso 1 1 calc R U . . .
H25B H 0.5517 0.4799 0.7164 0.107 Uiso 1 1 calc R U . . .
H25C H 0.6590 0.4516 0.6567 0.107 Uiso 1 1 calc R U . . .
C23 C 0.2728(4) 0.4975(5) 0.7497(3) 0.0740(15) Uani 1 1 d . . . . .
H23A H 0.3654 0.5259 0.7590 0.111 Uiso 1 1 calc R U . . .
H23B H 0.2574 0.4158 0.7738 0.111 Uiso 1 1 calc R U . . .
H23C H 0.2133 0.5665 0.7683 0.111 Uiso 1 1 calc R U . . .


_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 N3 1.612(3) . ?
P1 N2 1.620(3) . ?
P1 N1 1.621(3) . ?
P1 C13 1.824(3) . ?
P2 N5 1.609(3) . ?
P2 N6 1.613(3) . ?
P2 N4 1.616(3) . ?
P2 C26 1.813(4) . ?
N5 C20 1.486(4) . ?
N5 C18 1.487(4) . ?
N3 C9 1.482(4) . ?
N3 C11 1.486(4) . ?
F2 C26 1.393(4) . ?
N6 C22 1.483(5) . ?
N6 C24 1.500(4) . ?
F1 C13 1.378(4) . ?
N2 C7 1.474(4) . ?
N2 C5 1.479(4) . ?
N1 C3 1.473(5) . ?
N1 C1 1.479(4) . ?
C19 C18 1.506(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C13 H13A 0.99(2) . ?
C13 H13B 0.99(2) . ?
C5 C6 1.509(5) . ?
C5 H5A 0.99(2) . ?
C5 H5B 0.99(2) . ?
C7 C8 1.505(5) . ?
C7 H7A 0.90(2) . ?
C7 H7B 0.90(2) . ?
N4 C16 1.479(4) . ?
N4 C14 1.487(4) . ?
C11 C12 1.506(5) . ?
C11 H11A 0.96(2) . ?
C11 H11B 0.96(2) . ?
C16 C17 1.514(5) . ?
C16 H16A 0.95(2) . ?
C16 H16B 0.95(2) . ?
C2 C1 1.502(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C26 H26A 0.94(2) . ?
C26 H26B 0.94(2) . ?
C9 C10 1.506(5) . ?
C9 H9A 0.98(2) . ?
C9 H9B 0.98(2) . ?
C4 C3 1.516(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C15 C14 1.510(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C22 C23 1.482(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C14 H14A 0.93(2) . ?
C14 H14B 0.93(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C3 H3A 0.95(2) . ?
C3 H3B 0.95(2) . ?
C18 H18A 0.99(2) . ?
C18 H18B 0.99(2) . ?
C20 C21 1.497(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C1 H1A 1.00(3) . ?
C1 H1B 1.00(3) . ?
C24 C25 1.484(5) . ?
C24 H24A 0.94(3) . ?
C24 H24B 0.94(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
N3 P1 N2 112.70(14) . . ?
N3 P1 N1 109.02(15) . . ?
N2 P1 N1 111.44(15) . . ?
N3 P1 C13 106.66(16) . . ?
N2 P1 C13 106.38(16) . . ?
N1 P1 C13 110.50(15) . . ?
N5 P2 N6 113.43(16) . . ?
N5 P2 N4 109.36(14) . . ?
N6 P2 N4 110.78(16) . . ?
N5 P2 C26 105.52(17) . . ?
N6 P2 C26 106.79(16) . . ?
N4 P2 C26 110.81(17) . . ?
C20 N5 C18 116.1(3) . . ?
C20 N5 P2 123.5(2) . . ?
C18 N5 P2 120.3(2) . . ?
C9 N3 C11 116.0(3) . . ?
C9 N3 P1 123.5(2) . . ?
C11 N3 P1 119.5(2) . . ?
C22 N6 C24 115.7(3) . . ?
C22 N6 P2 121.5(2) . . ?
C24 N6 P2 119.4(2) . . ?
C7 N2 C5 116.4(3) . . ?
C7 N2 P1 120.6(2) . . ?
C5 N2 P1 121.4(2) . . ?
C3 N1 C1 116.5(3) . . ?
C3 N1 P1 123.1(2) . . ?
C1 N1 P1 120.4(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F1 C13 P1 112.5(2) . . ?
F1 C13 H13A 109.1 . . ?
P1 C13 H13A 109.1 . . ?
F1 C13 H13B 109.1 . . ?
P1 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
N2 C5 C6 113.1(3) . . ?
N2 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N2 C7 C8 114.5(3) . . ?
N2 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
N2 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C16 N4 C14 116.1(3) . . ?
C16 N4 P2 123.7(2) . . ?
C14 N4 P2 120.2(2) . . ?
N3 C11 C12 113.4(3) . . ?
N3 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N3 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
N4 C16 C17 114.2(3) . . ?
N4 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
N4 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
F2 C26 P2 112.8(3) . . ?
F2 C26 H26A 109.0 . . ?
P2 C26 H26A 109.0 . . ?
F2 C26 H26B 109.0 . . ?
P2 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
N3 C9 C10 112.8(3) . . ?
N3 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N3 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 C22 N6 113.6(3) . . ?
C23 C22 H22A 108.8 . . ?
N6 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
N6 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C14 C15 111.9(4) . . ?
N4 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N4 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C3 C4 113.7(3) . . ?
N1 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
N1 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
N5 C18 C19 112.8(3) . . ?
N5 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N5 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
N5 C20 C21 113.1(3) . . ?
N5 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
N5 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
N1 C1 C2 113.7(4) . . ?
N1 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
N1 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C25 C24 N6 114.3(3) . . ?
C25 C24 H24A 108.7 . . ?
N6 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
N6 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
N6 P2 N5 C20 -3.2(3) . . . . ?
N4 P2 N5 C20 121.0(3) . . . . ?
C26 P2 N5 C20 -119.8(3) . . . . ?
N6 P2 N5 C18 173.5(3) . . . . ?
N4 P2 N5 C18 -62.3(3) . . . . ?
C26 P2 N5 C18 56.9(3) . . . . ?
N2 P1 N3 C9 2.0(3) . . . . ?
N1 P1 N3 C9 126.3(3) . . . . ?
C13 P1 N3 C9 -114.3(3) . . . . ?
N2 P1 N3 C11 170.6(3) . . . . ?
N1 P1 N3 C11 -65.1(3) . . . . ?
C13 P1 N3 C11 54.3(3) . . . . ?
N5 P2 N6 C22 88.7(3) . . . . ?
N4 P2 N6 C22 -34.8(3) . . . . ?
C26 P2 N6 C22 -155.5(3) . . . . ?
N5 P2 N6 C24 -69.6(3) . . . . ?
N4 P2 N6 C24 167.0(3) . . . . ?
C26 P2 N6 C24 46.2(3) . . . . ?
N3 P1 N2 C7 -72.7(3) . . . . ?
N1 P1 N2 C7 164.3(3) . . . . ?
C13 P1 N2 C7 43.8(3) . . . . ?
N3 P1 N2 C5 91.9(3) . . . . ?
N1 P1 N2 C5 -31.1(3) . . . . ?
C13 P1 N2 C5 -151.6(3) . . . . ?
N3 P1 N1 C3 -18.4(3) . . . . ?
N2 P1 N1 C3 106.6(3) . . . . ?
C13 P1 N1 C3 -135.3(3) . . . . ?
N3 P1 N1 C1 160.8(3) . . . . ?
N2 P1 N1 C1 -74.2(3) . . . . ?
C13 P1 N1 C1 43.8(3) . . . . ?
N3 P1 C13 F1 173.1(2) . . . . ?
N2 P1 C13 F1 52.6(3) . . . . ?
N1 P1 C13 F1 -68.5(3) . . . . ?
C7 N2 C5 C6 -88.1(4) . . . . ?
P1 N2 C5 C6 106.7(3) . . . . ?
C5 N2 C7 C8 79.1(4) . . . . ?
P1 N2 C7 C8 -115.5(3) . . . . ?
N5 P2 N4 C16 -15.4(4) . . . . ?
N6 P2 N4 C16 110.3(3) . . . . ?
C26 P2 N4 C16 -131.3(3) . . . . ?
N5 P2 N4 C14 163.8(3) . . . . ?
N6 P2 N4 C14 -70.5(3) . . . . ?
C26 P2 N4 C14 47.9(4) . . . . ?
C9 N3 C11 C12 57.9(4) . . . . ?
P1 N3 C11 C12 -111.5(3) . . . . ?
C14 N4 C16 C17 51.6(5) . . . . ?
P2 N4 C16 C17 -129.2(3) . . . . ?
N5 P2 C26 F2 177.4(3) . . . . ?
N6 P2 C26 F2 56.4(3) . . . . ?
N4 P2 C26 F2 -64.4(3) . . . . ?
C11 N3 C9 C10 53.3(4) . . . . ?
P1 N3 C9 C10 -137.7(3) . . . . ?
C24 N6 C22 C23 -83.4(4) . . . . ?
P2 N6 C22 C23 117.6(4) . . . . ?
C16 N4 C14 C15 59.9(5) . . . . ?
P2 N4 C14 C15 -119.4(3) . . . . ?
C1 N1 C3 C4 51.5(4) . . . . ?
P1 N1 C3 C4 -129.3(3) . . . . ?
C20 N5 C18 C19 60.8(4) . . . . ?
P2 N5 C18 C19 -116.1(3) . . . . ?
C18 N5 C20 C21 56.0(5) . . . . ?
P2 N5 C20 C21 -127.2(3) . . . . ?
C3 N1 C1 C2 60.7(5) . . . . ?
P1 N1 C1 C2 -118.5(3) . . . . ?
C22 N6 C24 C25 90.3(4) . . . . ?
P2 N6 C24 C25 -110.2(4) . . . . ?

_refine_diff_density_max         1.020
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.097

_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_test1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1967517'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2020-04-04 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
(fluoromethyl)diphenylphosphine oxide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 F O P'
_chemical_formula_sum            'C13 H12 F O P'
_chemical_formula_weight         234.20

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   11.5552(17)
_cell_length_b                   13.7077(16)
_cell_length_c                   17.2666(11)
_cell_angle_alpha                69.635(9)
_cell_angle_beta                 78.081(9)
_cell_angle_gamma                65.391(13)
_cell_volume                     2325.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    4207
_cell_measurement_theta_min      4.2540
_cell_measurement_theta_max      30.2210

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            34798
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.104
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             9439
_reflns_number_gt                5636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.0638P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9439
_refine_ls_number_parameters     624
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_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
P1 P 0.05611(6) 0.31197(5) 0.24352(3) 0.01687(15) Uani 1 1 d . . . . .
H48 H 0.504(3) 1.044(2) 0.1852(16) 0.043(8) Uiso 1 1 d . . . . .
P2 P 0.55227(6) 0.31452(5) 0.24832(4) 0.01754(15) Uani 1 1 d . . . . .
P3 P 0.07270(6) 0.29990(5) 0.74595(4) 0.01706(15) Uani 1 1 d . . . . .
P4 P 0.42799(6) 0.70378(5) 0.24996(4) 0.01699(15) Uani 1 1 d . . . . .
F2 F 0.35852(14) 0.42025(12) 0.33850(9) 0.0358(4) Uani 1 1 d . . . . .
O3 O 0.16974(15) 0.32890(13) 0.76823(9) 0.0229(4) Uani 1 1 d . . . . .
O4 O 0.33002(15) 0.67904(12) 0.22452(9) 0.0216(4) Uani 1 1 d . . . . .
F4 F 0.61610(15) 0.61507(13) 0.15047(9) 0.0406(4) Uani 1 1 d . . . . .
O2 O 0.65014(15) 0.33758(13) 0.27507(9) 0.0233(4) Uani 1 1 d . . . . .
F1 F -0.13901(14) 0.41054(12) 0.33566(9) 0.0356(4) Uani 1 1 d . . . . .
F3 F -0.11738(15) 0.38907(13) 0.84429(9) 0.0375(4) Uani 1 1 d . . . . .
C1 C 0.0564(2) 0.17387(19) 0.30224(14) 0.0201(5) Uani 1 1 d . . . . .
O1 O 0.15138(15) 0.33960(13) 0.26916(9) 0.0230(4) Uani 1 1 d . . . . .
C26 C 0.3914(2) 0.41669(19) 0.25695(14) 0.0209(5) Uani 1 1 d . . . . .
H26A H 0.3867(2) 0.4916(12) 0.2201(6) 0.025 Uiso 1 1 calc R U . . .
H26B H 0.3307(10) 0.3959(4) 0.2396(3) 0.025 Uiso 1 1 calc R U . . .
C39 C -0.0904(2) 0.39375(19) 0.76109(14) 0.0197(5) Uani 1 1 d . . . . .
H39A H -0.1017(3) 0.4728(13) 0.7262(6) 0.024 Uiso 1 1 calc R U . . .
H39B H -0.1507(10) 0.3708(4) 0.7436(3) 0.024 Uiso 1 1 calc R U . . .
C40 C 0.4148(2) 0.68451(18) 0.35975(14) 0.0196(5) Uani 1 1 d . . . . .
C20 C 0.5751(2) 0.32513(18) 0.13977(14) 0.0187(5) Uani 1 1 d . . . . .
C9 C 0.1729(3) 0.3923(2) -0.00033(15) 0.0278(6) Uani 1 1 d . . . . .
H9 H 0.2208(14) 0.4348(12) -0.0353(10) 0.033 Uiso 1 1 calc R U . . .
C46 C 0.4199(2) 0.84521(18) 0.19283(14) 0.0189(5) Uani 1 1 d . . . . .
C14 C 0.5468(2) 0.17762(19) 0.30533(14) 0.0215(5) Uani 1 1 d . . . . .
C27 C 0.0882(2) 0.31431(18) 0.63659(13) 0.0175(5) Uani 1 1 d . . . . .
C13 C -0.1066(2) 0.41030(19) 0.25310(14) 0.0218(5) Uani 1 1 d . . . . .
H13A H -0.1140(3) 0.4856(13) 0.2177(6) 0.026 Uiso 1 1 calc R U . . .
H13B H -0.1649(10) 0.3884(4) 0.2354(3) 0.026 Uiso 1 1 calc R U . . .
C7 C 0.0791(2) 0.32154(18) 0.13515(13) 0.0177(5) Uani 1 1 d . . . . .
C38 C 0.1878(2) 0.0912(2) 0.85117(15) 0.0275(6) Uani 1 1 d . . . . .
H38 H 0.2507(17) 0.1180(8) 0.84913(16) 0.033 Uiso 1 1 calc R U . . .
C33 C 0.0805(2) 0.16021(19) 0.80610(14) 0.0206(5) Uani 1 1 d . . . . .
C45 C 0.3092(3) 0.6624(2) 0.40479(15) 0.0277(6) Uani 1 1 d . . . . .
H45 H 0.2512(17) 0.6588(2) 0.3785(8) 0.033 Uiso 1 1 calc R U . . .
C52 C 0.5909(2) 0.60962(19) 0.23344(14) 0.0213(5) Uani 1 1 d . . . . .
H52A H 0.6504(10) 0.6314(4) 0.2501(3) 0.026 Uiso 1 1 calc R U . . .
H52B H 0.6020(3) 0.5326(13) 0.2671(6) 0.026 Uiso 1 1 calc R U . . .
C6 C -0.0528(3) 0.1517(2) 0.33790(16) 0.0306(6) Uani 1 1 d . . . . .
H6 H -0.136(2) 0.2114(17) 0.3297(3) 0.037 Uiso 1 1 calc R U . . .
C31 C 0.1636(3) 0.4021(2) 0.49954(16) 0.0326(6) Uani 1 1 d . . . . .
H31 H 0.2041(12) 0.4528(14) 0.4638(10) 0.039 Uiso 1 1 calc R U . . .
C30 C 0.1225(2) 0.3452(2) 0.46630(16) 0.0294(6) Uani 1 1 d . . . . .
H30 H 0.1349(4) 0.3547(3) 0.4095(16) 0.035 Uiso 1 1 calc R U . . .
C25 C 0.5028(2) 0.29636(19) 0.10260(14) 0.0245(6) Uani 1 1 d . . . . .
H25 H 0.4398(17) 0.2702(7) 0.1341(9) 0.029 Uiso 1 1 calc R U . . .
C12 C 0.0296(2) 0.2697(2) 0.10142(15) 0.0264(6) Uani 1 1 d . . . . .
H12 H -0.0183(14) 0.2294(11) 0.1348(9) 0.032 Uiso 1 1 calc R U . . .
C21 C 0.6686(3) 0.3651(2) 0.09227(15) 0.0274(6) Uani 1 1 d . . . . .
H21 H 0.7155(14) 0.3848(6) 0.1164(7) 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4390(3) 0.1626(2) 0.35183(16) 0.0337(7) Uani 1 1 d . . . . .
H19 H 0.363(2) 0.2253(18) 0.35256(16) 0.040 Uiso 1 1 calc R U . . .
C24 C 0.5247(3) 0.3067(2) 0.01882(15) 0.0303(6) Uani 1 1 d . . . . .
H24 H 0.4758(14) 0.2880(6) -0.0062(7) 0.036 Uiso 1 1 calc R U . . .
C32 C 0.1470(2) 0.3869(2) 0.58465(15) 0.0263(6) Uani 1 1 d . . . . .
H32 H 0.1758(8) 0.4259(10) 0.6073(6) 0.032 Uiso 1 1 calc R U . . .
C37 C 0.2010(3) -0.0177(2) 0.89922(16) 0.0343(7) Uani 1 1 d . . . . .
H37 H 0.269(2) -0.0615(14) 0.9275(9) 0.041 Uiso 1 1 calc R U . . .
C41 C 0.5045(3) 0.6873(2) 0.40063(16) 0.0300(6) Uani 1 1 d . . . . .
H41 H 0.577(2) 0.6998(4) 0.3710(9) 0.036 Uiso 1 1 calc R U . . .
C10 C 0.1250(3) 0.3386(2) -0.03274(15) 0.0282(6) Uani 1 1 d . . . . .
H10 H 0.1414(5) 0.3428(2) -0.0876(16) 0.034 Uiso 1 1 calc R U . . .
C11 C 0.0523(3) 0.2785(2) 0.01792(15) 0.0313(6) Uani 1 1 d . . . . .
H11 H 0.0193(10) 0.2446(10) -0.0039(6) 0.038 Uiso 1 1 calc R U . . .
C49 C 0.3947(3) 1.0641(2) 0.10065(17) 0.0322(7) Uani 1 1 d . . . . .
H49 H 0.3853(4) 1.139(2) 0.0695(9) 0.039 Uiso 1 1 calc R U . . .
C8 C 0.1505(2) 0.38361(19) 0.08400(15) 0.0230(5) Uani 1 1 d . . . . .
H8 H 0.1831(9) 0.4191(9) 0.1060(6) 0.028 Uiso 1 1 calc R U . . .
C4 C 0.0768(3) -0.0423(2) 0.39651(17) 0.0345(7) Uani 1 1 d . . . . .
H4 H 0.0836(3) -0.117(2) 0.4298(10) 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1851(3) -0.0214(2) 0.36005(18) 0.0397(7) Uani 1 1 d . . . . .
H3 H 0.264(3) -0.0789(18) 0.3670(3) 0.048 Uiso 1 1 calc R U . . .
C23 C 0.6187(3) 0.3445(2) -0.02811(16) 0.0295(6) Uani 1 1 d . . . . .
H23 H 0.6338(5) 0.3495(2) -0.0832(16) 0.035 Uiso 1 1 calc R U . . .
C2 C 0.1753(3) 0.0862(2) 0.31289(17) 0.0354(7) Uani 1 1 d . . . . .
H2 H 0.252(2) 0.1007(5) 0.2871(8) 0.042 Uiso 1 1 calc R U . . .
C5 C -0.0408(3) 0.0432(2) 0.38549(18) 0.0392(7) Uani 1 1 d . . . . .
H5 H -0.116(2) 0.0279(5) 0.4109(8) 0.047 Uiso 1 1 calc R U . . .
C43 C 0.3796(3) 0.6518(2) 0.53002(17) 0.0349(7) Uani 1 1 d . . . . .
H43 H 0.3675(5) 0.6432(3) 0.5843(17) 0.042 Uiso 1 1 calc R U . . .
C48 C 0.4673(3) 1.0097(2) 0.16818(18) 0.0344(7) Uani 1 1 d . . . . .
C47 C 0.4801(3) 0.9007(2) 0.21404(16) 0.0309(6) Uani 1 1 d . . . . .
H47 H 0.5263(14) 0.8666(11) 0.2566(13) 0.037 Uiso 1 1 calc R U . . .
C22 C 0.6900(3) 0.3748(2) 0.00816(15) 0.0310(6) Uani 1 1 d . . . . .
H22 H 0.7532(18) 0.4020(8) -0.0243(9) 0.037 Uiso 1 1 calc R U . . .
C51 C 0.3481(3) 0.9003(2) 0.12421(15) 0.0312(6) Uani 1 1 d . . . . .
H51 H 0.3073(12) 0.8634(10) 0.1086(5) 0.037 Uiso 1 1 calc R U . . .
C34 C -0.0145(3) 0.1199(2) 0.81171(16) 0.0324(6) Uani 1 1 d . . . . .
H34 H -0.091(2) 0.1680(14) 0.7826(9) 0.039 Uiso 1 1 calc R U . . .
C42 C 0.4868(3) 0.6714(2) 0.48545(17) 0.0360(7) Uani 1 1 d . . . . .
H42 H 0.5479(19) 0.6740(2) 0.5131(8) 0.043 Uiso 1 1 calc R U . . .
C29 C 0.0627(3) 0.2739(2) 0.51739(16) 0.0353(7) Uani 1 1 d . . . . .
H29 H 0.0350(9) 0.2371(11) 0.4953(7) 0.042 Uiso 1 1 calc R U . . .
C36 C 0.1070(3) -0.0573(2) 0.90265(17) 0.0366(7) Uani 1 1 d . . . . .
H36 H 0.1163(4) -0.133(2) 0.9358(10) 0.044 Uiso 1 1 calc R U . . .
C50 C 0.3357(3) 1.0096(2) 0.07820(17) 0.0392(7) Uani 1 1 d . . . . .
H50 H 0.2869(15) 1.0466(12) 0.0315(14) 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6572(3) 0.0844(2) 0.30297(17) 0.0391(7) Uani 1 1 d . . . . .
H15 H 0.735(2) 0.0942(4) 0.2691(10) 0.047 Uiso 1 1 calc R U . . .
C28 C 0.0450(3) 0.2585(2) 0.60231(15) 0.0311(6) Uani 1 1 d . . . . .
H28 H 0.0039(12) 0.2104(14) 0.6366(10) 0.037 Uiso 1 1 calc R U . . .
C35 C 0.0005(3) 0.0108(2) 0.85899(19) 0.0449(8) Uani 1 1 d . . . . .
H35 H -0.062(2) -0.0163(9) 0.8612(2) 0.054 Uiso 1 1 calc R U . . .
C44 C 0.2921(3) 0.6457(2) 0.48988(16) 0.0349(7) Uani 1 1 d . . . . .
H44 H 0.220(2) 0.6300(5) 0.5206(9) 0.042 Uiso 1 1 calc R U . . .
C16 C 0.6599(4) -0.0219(2) 0.34719(19) 0.0524(10) Uani 1 1 d . . . . .
H16 H 0.734(3) -0.084(2) 0.3447(2) 0.063 Uiso 1 1 calc R U . . .
C17 C 0.5546(4) -0.0367(2) 0.39453(18) 0.0460(9) Uani 1 1 d . . . . .
H17 H 0.5579(4) -0.111(2) 0.4258(10) 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4436(3) 0.0551(2) 0.39744(18) 0.0444(8) Uani 1 1 d . . . . .
H18 H 0.370(2) 0.0450(4) 0.4306(11) 0.053 Uiso 1 1 calc R U . . .


_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 O1 1.4889(16) . ?
P1 C7 1.801(2) . ?
P1 C1 1.809(2) . ?
P1 C13 1.815(2) . ?
P2 O2 1.4857(16) . ?
P2 C20 1.800(2) . ?
P2 C14 1.812(2) . ?
P2 C26 1.817(2) . ?
P3 O3 1.4897(16) . ?
P3 C33 1.807(2) . ?
P3 C27 1.807(2) . ?
P3 C39 1.813(2) . ?
P4 O4 1.4893(16) . ?
P4 C40 1.803(2) . ?
P4 C46 1.816(2) . ?
P4 C52 1.817(2) . ?
F2 C26 1.393(2) . ?
F4 C52 1.383(3) . ?
F1 C13 1.398(2) . ?
F3 C39 1.390(2) . ?
C1 C6 1.389(3) . ?
C1 C2 1.393(3) . ?
C26 H26A 0.987(16) . ?
C26 H26B 0.987(16) . ?
C39 H39A 1.006(16) . ?
C39 H39B 1.006(16) . ?
C40 C41 1.388(3) . ?
C40 C45 1.392(3) . ?
C20 C25 1.392(3) . ?
C20 C21 1.398(3) . ?
C9 C10 1.384(3) . ?
C9 C8 1.397(3) . ?
C9 H9 0.95(3) . ?
C46 C51 1.387(3) . ?
C46 C47 1.391(3) . ?
C14 C15 1.385(3) . ?
C14 C19 1.387(3) . ?
C27 C28 1.393(3) . ?
C27 C32 1.395(3) . ?
C13 H13A 0.978(16) . ?
C13 H13B 0.978(16) . ?
C7 C12 1.391(3) . ?
C7 C8 1.395(3) . ?
C38 C37 1.394(3) . ?
C38 C33 1.396(3) . ?
C38 H38 0.93(2) . ?
C33 C34 1.395(3) . ?
C45 C44 1.391(3) . ?
C45 H45 0.91(3) . ?
C52 H52A 0.979(16) . ?
C52 H52B 0.979(16) . ?
C6 C5 1.390(3) . ?
C6 H6 0.97(3) . ?
C31 C30 1.377(4) . ?
C31 C32 1.394(3) . ?
C31 H31 0.97(3) . ?
C30 C29 1.386(4) . ?
C30 H30 0.93(3) . ?
C25 C24 1.383(3) . ?
C25 H25 0.93(2) . ?
C12 C11 1.383(3) . ?
C12 H12 0.92(2) . ?
C21 C22 1.390(3) . ?
C21 H21 0.91(3) . ?
C19 C18 1.393(3) . ?
C19 H19 0.94(3) . ?
C24 C23 1.385(4) . ?
C24 H24 0.93(3) . ?
C32 H32 0.95(2) . ?
C37 C36 1.385(4) . ?
C37 H37 0.88(3) . ?
C41 C42 1.388(3) . ?
C41 H41 0.93(3) . ?
C10 C11 1.387(4) . ?
C10 H10 0.91(3) . ?
C11 H11 0.91(3) . ?
C49 C48 1.377(4) . ?
C49 C50 1.381(4) . ?
C49 H49 0.95(3) . ?
C8 H8 0.93(2) . ?
C4 C5 1.372(4) . ?
C4 C3 1.375(4) . ?
C4 H4 0.96(3) . ?
C3 C2 1.384(4) . ?
C3 H3 0.92(3) . ?
C23 C22 1.387(4) . ?
C23 H23 0.91(3) . ?
C2 H2 0.97(3) . ?
C5 H5 0.96(3) . ?
C43 C44 1.383(4) . ?
C43 C42 1.392(4) . ?
C43 H43 0.89(3) . ?
C48 C47 1.386(3) . ?
C48 H48 0.90(3) . ?
C47 H47 0.87(3) . ?
C22 H22 0.95(3) . ?
C51 C50 1.391(3) . ?
C51 H51 0.95(3) . ?
C34 C35 1.387(3) . ?
C34 H34 0.97(3) . ?
C42 H42 0.95(3) . ?
C29 C28 1.390(3) . ?
C29 H29 0.91(3) . ?
C36 C35 1.375(4) . ?
C36 H36 0.97(3) . ?
C50 H50 0.94(3) . ?
C15 C16 1.381(4) . ?
C15 H15 1.00(3) . ?
C28 H28 0.94(3) . ?
C35 H35 0.93(3) . ?
C44 H44 0.96(3) . ?
C16 C17 1.367(4) . ?
C16 H16 0.93(3) . ?
C17 C18 1.380(4) . ?
C17 H17 0.96(3) . ?
C18 H18 0.95(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 P1 C7 112.19(10) . . ?
O1 P1 C1 113.16(10) . . ?
C7 P1 C1 108.26(10) . . ?
O1 P1 C13 113.31(10) . . ?
C7 P1 C13 102.72(11) . . ?
C1 P1 C13 106.50(11) . . ?
O2 P2 C20 112.28(10) . . ?
O2 P2 C14 113.45(10) . . ?
C20 P2 C14 107.72(10) . . ?
O2 P2 C26 113.50(10) . . ?
C20 P2 C26 102.41(11) . . ?
C14 P2 C26 106.71(11) . . ?
O3 P3 C33 111.91(10) . . ?
O3 P3 C27 111.41(10) . . ?
C33 P3 C27 110.17(10) . . ?
O3 P3 C39 113.87(10) . . ?
C33 P3 C39 106.31(11) . . ?
C27 P3 C39 102.68(10) . . ?
O4 P4 C40 112.71(10) . . ?
O4 P4 C46 110.79(10) . . ?
C40 P4 C46 109.94(10) . . ?
O4 P4 C52 113.94(10) . . ?
C40 P4 C52 102.19(11) . . ?
C46 P4 C52 106.82(11) . . ?
C6 C1 C2 119.3(2) . . ?
C6 C1 P1 124.21(19) . . ?
C2 C1 P1 116.45(19) . . ?
F2 C26 P2 109.91(16) . . ?
F2 C26 H26A 109.7 . . ?
P2 C26 H26A 109.7 . . ?
F2 C26 H26B 109.7 . . ?
P2 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
F3 C39 P3 109.13(16) . . ?
F3 C39 H39A 109.9 . . ?
P3 C39 H39A 109.9 . . ?
F3 C39 H39B 109.9 . . ?
P3 C39 H39B 109.9 . . ?
H39A C39 H39B 108.3 . . ?
C41 C40 C45 119.5(2) . . ?
C41 C40 P4 123.93(19) . . ?
C45 C40 P4 116.50(19) . . ?
C25 C20 C21 119.9(2) . . ?
C25 C20 P2 122.46(18) . . ?
C21 C20 P2 117.60(18) . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C51 C46 C47 118.8(2) . . ?
C51 C46 P4 117.04(18) . . ?
C47 C46 P4 124.14(19) . . ?
C15 C14 C19 119.2(2) . . ?
C15 C14 P2 117.6(2) . . ?
C19 C14 P2 123.18(19) . . ?
C28 C27 C32 119.3(2) . . ?
C28 C27 P3 124.15(18) . . ?
C32 C27 P3 116.59(17) . . ?
F1 C13 P1 109.18(16) . . ?
F1 C13 H13A 109.8 . . ?
P1 C13 H13A 109.8 . . ?
F1 C13 H13B 109.8 . . ?
P1 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C12 C7 C8 119.6(2) . . ?
C12 C7 P1 122.91(18) . . ?
C8 C7 P1 117.52(17) . . ?
C37 C38 C33 120.1(3) . . ?
C37 C38 H38 120.0 . . ?
C33 C38 H38 120.0 . . ?
C34 C33 C38 119.2(2) . . ?
C34 C33 P3 124.21(19) . . ?
C38 C33 P3 116.55(19) . . ?
C44 C45 C40 120.3(3) . . ?
C44 C45 H45 119.9 . . ?
C40 C45 H45 119.9 . . ?
F4 C52 P4 109.16(16) . . ?
F4 C52 H52A 109.8 . . ?
P4 C52 H52A 109.8 . . ?
F4 C52 H52B 109.8 . . ?
P4 C52 H52B 109.8 . . ?
H52A C52 H52B 108.3 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C30 C31 C32 120.1(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C30 C29 120.0(2) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C24 C25 C20 119.7(2) . . ?
C24 C25 H25 120.2 . . ?
C20 C25 H25 120.2 . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C14 C19 C18 120.1(3) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C31 C32 C27 120.2(2) . . ?
C31 C32 H32 119.9 . . ?
C27 C32 H32 119.9 . . ?
C36 C37 C38 120.0(3) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C42 C41 C40 120.1(3) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C48 C49 C50 120.0(3) . . ?
C48 C49 H49 120.0 . . ?
C50 C49 H49 120.0 . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C44 C43 C42 119.8(3) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C49 C48 C47 120.0(3) . . ?
C49 C48 H48 121.6(18) . . ?
C47 C48 H48 118.3(18) . . ?
C48 C47 C46 120.7(3) . . ?
C48 C47 H47 119.6 . . ?
C46 C47 H47 119.6 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C46 C51 C50 120.3(3) . . ?
C46 C51 H51 119.8 . . ?
C50 C51 H51 119.8 . . ?
C35 C34 C33 120.1(3) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C41 C42 C43 120.2(3) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C30 C29 C28 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C35 C36 C37 120.1(3) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C49 C50 C51 120.2(3) . . ?
C49 C50 H50 119.9 . . ?
C51 C50 H50 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C29 C28 C27 120.0(2) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C36 C35 C34 120.5(3) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C43 C44 C45 120.0(3) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?

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
O1 P1 C1 C6 132.0(2) . . . . ?
C7 P1 C1 C6 -103.0(2) . . . . ?
C13 P1 C1 C6 6.9(2) . . . . ?
O1 P1 C1 C2 -46.5(2) . . . . ?
C7 P1 C1 C2 78.5(2) . . . . ?
C13 P1 C1 C2 -171.65(19) . . . . ?
O2 P2 C26 F2 -58.02(18) . . . . ?
C20 P2 C26 F2 -179.28(15) . . . . ?
C14 P2 C26 F2 67.68(17) . . . . ?
O3 P3 C39 F3 -60.96(17) . . . . ?
C33 P3 C39 F3 62.73(17) . . . . ?
C27 P3 C39 F3 178.46(15) . . . . ?
O4 P4 C40 C41 170.94(19) . . . . ?
C46 P4 C40 C41 -64.9(2) . . . . ?
C52 P4 C40 C41 48.2(2) . . . . ?
O4 P4 C40 C45 -7.1(2) . . . . ?
C46 P4 C40 C45 117.08(19) . . . . ?
C52 P4 C40 C45 -129.77(19) . . . . ?
O2 P2 C20 C25 173.53(18) . . . . ?
C14 P2 C20 C25 47.9(2) . . . . ?
C26 P2 C20 C25 -64.4(2) . . . . ?
O2 P2 C20 C21 -7.1(2) . . . . ?
C14 P2 C20 C21 -132.76(19) . . . . ?
C26 P2 C20 C21 115.0(2) . . . . ?
O4 P4 C46 C51 -13.2(2) . . . . ?
C40 P4 C46 C51 -138.47(19) . . . . ?
C52 P4 C46 C51 111.4(2) . . . . ?
O4 P4 C46 C47 166.33(19) . . . . ?
C40 P4 C46 C47 41.1(2) . . . . ?
C52 P4 C46 C47 -69.0(2) . . . . ?
O2 P2 C14 C15 -58.7(2) . . . . ?
C20 P2 C14 C15 66.2(2) . . . . ?
C26 P2 C14 C15 175.52(19) . . . . ?
O2 P2 C14 C19 120.0(2) . . . . ?
C20 P2 C14 C19 -115.1(2) . . . . ?
C26 P2 C14 C19 -5.8(2) . . . . ?
O3 P3 C27 C28 156.6(2) . . . . ?
C33 P3 C27 C28 31.8(2) . . . . ?
C39 P3 C27 C28 -81.1(2) . . . . ?
O3 P3 C27 C32 -23.7(2) . . . . ?
C33 P3 C27 C32 -148.52(18) . . . . ?
C39 P3 C27 C32 98.57(19) . . . . ?
O1 P1 C13 F1 -59.67(18) . . . . ?
C7 P1 C13 F1 179.08(15) . . . . ?
C1 P1 C13 F1 65.39(17) . . . . ?
O1 P1 C7 C12 160.55(19) . . . . ?
C1 P1 C7 C12 35.0(2) . . . . ?
C13 P1 C7 C12 -77.4(2) . . . . ?
O1 P1 C7 C8 -19.1(2) . . . . ?
C1 P1 C7 C8 -144.66(18) . . . . ?
C13 P1 C7 C8 102.95(19) . . . . ?
C37 C38 C33 C34 1.8(4) . . . . ?
C37 C38 C33 P3 179.93(19) . . . . ?
O3 P3 C33 C34 165.5(2) . . . . ?
C27 P3 C33 C34 -70.0(2) . . . . ?
C39 P3 C33 C34 40.6(2) . . . . ?
O3 P3 C33 C38 -12.5(2) . . . . ?
C27 P3 C33 C38 112.00(19) . . . . ?
C39 P3 C33 C38 -137.44(18) . . . . ?
C41 C40 C45 C44 1.5(4) . . . . ?
P4 C40 C45 C44 179.57(19) . . . . ?
O4 P4 C52 F4 58.18(18) . . . . ?
C40 P4 C52 F4 -179.95(15) . . . . ?
C46 P4 C52 F4 -64.50(18) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
P1 C1 C6 C5 -176.6(2) . . . . ?
C32 C31 C30 C29 1.0(4) . . . . ?
C21 C20 C25 C24 0.5(3) . . . . ?
P2 C20 C25 C24 179.83(19) . . . . ?
C8 C7 C12 C11 0.7(4) . . . . ?
P1 C7 C12 C11 -178.88(19) . . . . ?
C25 C20 C21 C22 -0.7(4) . . . . ?
P2 C20 C21 C22 179.94(19) . . . . ?
C15 C14 C19 C18 1.9(4) . . . . ?
P2 C14 C19 C18 -176.8(2) . . . . ?
C20 C25 C24 C23 0.5(4) . . . . ?
C30 C31 C32 C27 -0.3(4) . . . . ?
C28 C27 C32 C31 -0.8(4) . . . . ?
P3 C27 C32 C31 179.5(2) . . . . ?
C33 C38 C37 C36 -0.4(4) . . . . ?
C45 C40 C41 C42 -2.0(4) . . . . ?
P4 C40 C41 C42 -179.90(19) . . . . ?
C8 C9 C10 C11 1.5(4) . . . . ?
C7 C12 C11 C10 0.3(4) . . . . ?
C9 C10 C11 C12 -1.5(4) . . . . ?
C12 C7 C8 C9 -0.6(4) . . . . ?
P1 C7 C8 C9 179.00(19) . . . . ?
C10 C9 C8 C7 -0.5(4) . . . . ?
C5 C4 C3 C2 0.6(4) . . . . ?
C25 C24 C23 C22 -1.4(4) . . . . ?
C4 C3 C2 C1 0.2(4) . . . . ?
C6 C1 C2 C3 -1.5(4) . . . . ?
P1 C1 C2 C3 177.1(2) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C1 C6 C5 C4 -1.1(4) . . . . ?
C50 C49 C48 C47 -0.6(4) . . . . ?
C49 C48 C47 C46 -0.2(4) . . . . ?
C51 C46 C47 C48 0.8(4) . . . . ?
P4 C46 C47 C48 -178.7(2) . . . . ?
C24 C23 C22 C21 1.2(4) . . . . ?
C20 C21 C22 C23 -0.2(4) . . . . ?
C47 C46 C51 C50 -0.7(4) . . . . ?
P4 C46 C51 C50 178.9(2) . . . . ?
C38 C33 C34 C35 -2.6(4) . . . . ?
P3 C33 C34 C35 179.5(2) . . . . ?
C40 C41 C42 C43 0.5(4) . . . . ?
C44 C43 C42 C41 1.4(4) . . . . ?
C31 C30 C29 C28 -0.6(4) . . . . ?
C38 C37 C36 C35 -0.3(4) . . . . ?
C48 C49 C50 C51 0.8(4) . . . . ?
C46 C51 C50 C49 -0.1(4) . . . . ?
C19 C14 C15 C16 -0.7(4) . . . . ?
P2 C14 C15 C16 178.1(2) . . . . ?
C30 C29 C28 C27 -0.4(4) . . . . ?
C32 C27 C28 C29 1.1(4) . . . . ?
P3 C27 C28 C29 -179.2(2) . . . . ?
C37 C36 C35 C34 -0.5(4) . . . . ?
C33 C34 C35 C36 1.9(4) . . . . ?
C42 C43 C44 C45 -1.9(4) . . . . ?
C40 C45 C44 C43 0.4(4) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 C18 1.0(5) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C14 C19 C18 C17 -1.7(4) . . . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.059

_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_test1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1967514'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2020-04-04 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
tris(2-cyanoethyl)(fluoromethyl)phosphonium iodide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 F N3 P, I'
_chemical_formula_sum            'C10 H14 F I N3 P'
_chemical_formula_weight         353.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   8.7566(2)
_cell_length_b                   9.3257(3)
_cell_length_c                   17.2049(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.741(2)
_cell_angle_gamma                90
_cell_volume                     1380.36(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    7216
_cell_measurement_theta_min      4.5000
_cell_measurement_theta_max      32.2870

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.307
_exptl_crystal_size_min          0.165
_exptl_absorpt_coefficient_mu    2.427
_shelx_estimated_absorpt_T_min   0.449
_shelx_estimated_absorpt_T_max   0.690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            27409
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.226
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4202
_reflns_number_gt                3398
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0188P)²+0.9227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4202
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0547
_refine_ls_wR_factor_gt          0.0497
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_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
I1 I 0.26404(2) 0.50419(2) 0.37597(2) 0.02569(5) Uani 1 1 d . . . . .
P1 P 0.28101(6) 0.28190(5) 0.62292(3) 0.01633(9) Uani 1 1 d . . . . .
C2 C 0.4006(2) 0.2338(2) 0.55293(11) 0.0201(4) Uani 1 1 d . . . . .
H2A H 0.4428(8) 0.3157(14) 0.5368(3) 0.024 Uiso 1 1 calc R U . . .
H2B H 0.4808(14) 0.1783(9) 0.5782(4) 0.024 Uiso 1 1 calc R U . . .
C6 C 0.0362(3) 0.1765(2) 0.68826(13) 0.0270(4) Uani 1 1 d . . . . .
H6A H 0.0900(10) 0.2024(5) 0.7371(9) 0.032 Uiso 1 1 calc R U . . .
H6B H -0.0218(11) 0.2537(14) 0.6672(4) 0.032 Uiso 1 1 calc R U . . .
F1 F 0.50471(16) 0.18828(15) 0.73068(8) 0.0362(3) Uani 1 1 d . . . . .
N2 N -0.1499(2) -0.0337(2) 0.70425(14) 0.0412(5) Uani 1 1 d . . . . .
C10 C 0.1654(2) 0.7014(2) 0.56757(13) 0.0270(4) Uani 1 1 d . . . . .
C9 C 0.2645(2) 0.5816(2) 0.60182(13) 0.0259(4) Uani 1 1 d . . . . .
H9A H 0.3025(7) 0.5990(4) 0.6571(10) 0.031 Uiso 1 1 calc R U . . .
H9B H 0.3525(16) 0.5736(3) 0.5760(5) 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1517(2) 0.1369(2) 0.63471(12) 0.0213(4) Uani 1 1 d . . . . .
H5A H 0.0976(10) 0.1108(5) 0.5860(9) 0.026 Uiso 1 1 calc R U . . .
H5B H 0.2093(10) 0.0595(14) 0.6558(4) 0.026 Uiso 1 1 calc R U . . .
C4 C 0.4336(2) 0.1240(2) 0.42939(11) 0.0218(4) Uani 1 1 d . . . . .
N3 N 0.0865(2) 0.7921(2) 0.54059(14) 0.0427(5) Uani 1 1 d . . . . .
N1 N 0.5296(2) 0.1017(2) 0.39417(10) 0.0283(4) Uani 1 1 d . . . . .
C8 C 0.1710(2) 0.4419(2) 0.59150(12) 0.0192(4) Uani 1 1 d . . . . .
H8A H 0.1265(8) 0.4321(3) 0.5388(9) 0.023 Uiso 1 1 calc R U . . .
H8B H 0.0914(14) 0.4492(2) 0.6196(5) 0.023 Uiso 1 1 calc R U . . .
C1 C 0.4137(2) 0.3101(2) 0.71635(11) 0.0230(4) Uani 1 1 d . . . . .
H1A H 0.4756(11) 0.3903(14) 0.71319(12) 0.028 Uiso 1 1 calc R U . . .
H1B H 0.3583(10) 0.3245(4) 0.7569(7) 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3187(2) 0.1528(2) 0.47937(11) 0.0210(4) Uani 1 1 d . . . . .
H3A H 0.2776(8) 0.0667(15) 0.4941(3) 0.025 Uiso 1 1 calc R U . . .
H3B H 0.2374(14) 0.2080(9) 0.4517(5) 0.025 Uiso 1 1 calc R U . . .
C7 C -0.0671(2) 0.0575(2) 0.69691(13) 0.0279(4) 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 C2 1.7939(19) . ?
P1 C5 1.7987(19) . ?
P1 C8 1.8036(19) . ?
P1 C1 1.8184(19) . ?
C2 C3 1.532(3) . ?
C2 H2A 0.915(15) . ?
C2 H2B 0.915(15) . ?
C6 C7 1.457(3) . ?
C6 C5 1.535(3) . ?
C6 H6A 0.916(16) . ?
C6 H6B 0.916(16) . ?
F1 C1 1.384(2) . ?
N2 C7 1.140(3) . ?
C10 N3 1.136(3) . ?
C10 C9 1.469(3) . ?
C9 C8 1.531(3) . ?
C9 H9A 0.962(17) . ?
C9 H9B 0.962(17) . ?
C5 H5A 0.916(16) . ?
C5 H5B 0.916(16) . ?
C4 N1 1.143(3) . ?
C4 C3 1.465(3) . ?
C8 H8A 0.922(16) . ?
C8 H8B 0.922(16) . ?
C1 H1A 0.931(16) . ?
C1 H1B 0.931(16) . ?
C3 H3A 0.934(16) . ?
C3 H3B 0.934(16) . ?

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 P1 C5 110.25(9) . . ?
C2 P1 C8 110.60(9) . . ?
C5 P1 C8 110.09(9) . . ?
C2 P1 C1 105.84(9) . . ?
C5 P1 C1 108.71(10) . . ?
C8 P1 C1 111.27(9) . . ?
C3 C2 P1 115.85(13) . . ?
C3 C2 H2A 108.3 . . ?
P1 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
P1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C7 C6 C5 111.70(18) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N3 C10 C9 178.6(2) . . ?
C10 C9 C8 109.71(17) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C6 C5 P1 112.72(14) . . ?
C6 C5 H5A 109.0 . . ?
P1 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
P1 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N1 C4 C3 176.1(2) . . ?
C9 C8 P1 115.13(13) . . ?
C9 C8 H8A 108.5 . . ?
P1 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
P1 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
F1 C1 P1 106.89(13) . . ?
F1 C1 H1A 110.3 . . ?
P1 C1 H1A 110.3 . . ?
F1 C1 H1B 110.3 . . ?
P1 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
C4 C3 C2 107.96(16) . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N2 C7 C6 178.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 P1 C2 C3 41.17(17) . . . . ?
C8 P1 C2 C3 -80.81(16) . . . . ?
C1 P1 C2 C3 158.57(14) . . . . ?
C7 C6 C5 P1 -179.99(15) . . . . ?
C2 P1 C5 C6 -174.85(14) . . . . ?
C8 P1 C5 C6 -52.57(17) . . . . ?
C1 P1 C5 C6 69.55(16) . . . . ?
C10 C9 C8 P1 174.86(15) . . . . ?
C2 P1 C8 C9 -74.58(16) . . . . ?
C5 P1 C8 C9 163.34(15) . . . . ?
C1 P1 C8 C9 42.75(18) . . . . ?
C2 P1 C1 F1 -52.98(16) . . . . ?
C5 P1 C1 F1 65.44(15) . . . . ?
C8 P1 C1 F1 -173.17(13) . . . . ?
P1 C2 C3 C4 179.59(13) . . . . ?

_refine_diff_density_max         0.916
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.082

_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_test1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1967515'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2020-04-04 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H30 F O P2, I, 0.284(H2 O)'
_chemical_formula_sum            'C37 H30.57 F I O1.28 P2'
_chemical_formula_weight         703.57

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   11.3894(4)
_cell_length_b                   13.0313(6)
_cell_length_c                   13.4302(4)
_cell_angle_alpha                64.227(4)
_cell_angle_beta                 66.641(3)
_cell_angle_gamma                68.195(4)
_cell_volume                     1599.41(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9356
_cell_measurement_theta_min      4.4330
_cell_measurement_theta_max      32.0750

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             710
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.136
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            32102
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.110
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             9734
_reflns_number_gt                7866
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_refine_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+1.4210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9734
_refine_ls_number_parameters     422
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_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
I1 I 0.28798(2) 0.12770(2) 0.75565(2) 0.03563(6) Uani 1 1 d . . . . .
P2 P 0.17338(6) 0.46822(5) 0.16748(5) 0.02383(12) Uani 1 1 d . . . . .
P1 P -0.00241(6) 0.22381(5) 0.55371(5) 0.02181(12) Uani 1 1 d . . . . .
O1 O 0.22289(16) 0.27838(14) 0.36446(15) 0.0280(4) Uani 1 1 d . . . . .
C14 C 0.1482(2) 0.11954(19) 0.51993(18) 0.0208(4) Uani 1 1 d . . . . .
C11 C -0.1911(3) 0.4119(3) 0.2589(3) 0.0451(7) Uani 1 1 d . . . . .
H11 H -0.2332(16) 0.4542(16) 0.193(2) 0.054 Uiso 1 1 calc R U . . .
C22 C 0.4499(3) 0.4127(2) 0.3733(2) 0.0324(5) Uani 1 1 d . . . . .
H22 H 0.5026(18) 0.4009(5) 0.4181(16) 0.039 Uiso 1 1 calc R U . . .
C2 C -0.1135(2) 0.1515(2) 0.6810(2) 0.0254(4) Uani 1 1 d . . . . .
C15 C 0.1655(2) -0.0001(2) 0.5834(2) 0.0250(4) Uani 1 1 d . . . . .
H15 H 0.095(2) -0.0289(9) 0.646(2) 0.030 Uiso 1 1 calc R U . . .
C13 C -0.0363(3) 0.2503(2) 0.3504(2) 0.0299(5) Uani 1 1 d . . . . .
H13 H 0.028(2) 0.182(2) 0.3514(2) 0.036 Uiso 1 1 calc R U . . .
C19 C 0.2527(2) 0.1602(2) 0.42808(19) 0.0230(4) Uani 1 1 d . . . . .
C25 C 0.2931(2) 0.45011(19) 0.23794(19) 0.0221(4) Uani 1 1 d . . . . .
C16 C 0.2861(3) -0.0769(2) 0.5546(2) 0.0285(5) Uani 1 1 d . . . . .
H16 H 0.2975(5) -0.151(3) 0.5937(15) 0.034 Uiso 1 1 calc R U . . .
C1 C 0.0365(3) 0.3308(2) 0.5824(2) 0.0305(5) Uani 1 1 d . . . . .
H1A H 0.0890(13) 0.2914(9) 0.6338(12) 0.037 Uiso 1 1 calc R U . . .
H1B H 0.0844(12) 0.3780(11) 0.5132(16) 0.037 Uiso 1 1 calc R U . . .
F1 F -0.07871(17) 0.40001(15) 0.62946(16) 0.0438(4) Uani 1 1 d . . . . .
C20 C 0.3039(2) 0.3509(2) 0.33571(19) 0.0233(4) Uani 1 1 d . . . . .
C17 C 0.3877(2) -0.0344(2) 0.4630(2) 0.0299(5) Uani 1 1 d . . . . .
H17 H 0.4696 -0.0876 0.4436 0.036 Uiso 1 1 calc R U . . .
C12 C -0.0962(3) 0.3085(3) 0.2612(2) 0.0378(6) Uani 1 1 d . . . . .
H12 H -0.0729(10) 0.2785(13) 0.205(2) 0.045 Uiso 1 1 calc R U . . .
C32 C 0.1813(2) 0.6105(2) 0.0530(2) 0.0260(5) Uani 1 1 d . . . . .
C23 C 0.4426(3) 0.5123(2) 0.2755(2) 0.0323(5) Uani 1 1 d . . . . .
H23 H 0.4904(17) 0.567(2) 0.2544(8) 0.039 Uiso 1 1 calc R U . . .
C24 C 0.3645(2) 0.5305(2) 0.2093(2) 0.0272(5) Uani 1 1 d . . . . .
H24 H 0.3597(3) 0.597(2) 0.145(2) 0.033 Uiso 1 1 calc R U . . .
C26 C 0.2672(2) 0.3690(2) 0.08427(19) 0.0242(4) Uani 1 1 d . . . . .
C18 C 0.3726(2) 0.0837(2) 0.3992(2) 0.0290(5) Uani 1 1 d . . . . .
H18 H 0.436(2) 0.1089(10) 0.343(2) 0.035 Uiso 1 1 calc R U . . .
C37 C 0.2869(3) 0.6317(2) -0.0448(2) 0.0328(5) Uani 1 1 d . . . . .
H37 H 0.361(3) 0.570(2) -0.0557(5) 0.039 Uiso 1 1 calc R U . . .
C3 C -0.1035(3) 0.1294(2) 0.7892(2) 0.0318(5) Uani 1 1 d . . . . .
H3 H -0.039(2) 0.1546(9) 0.7957(3) 0.038 Uiso 1 1 calc R U . . .
C31 C 0.2032(3) 0.3591(2) 0.0208(2) 0.0317(5) Uani 1 1 d . . . . .
H31 H 0.116(3) 0.3993(15) 0.0249(3) 0.038 Uiso 1 1 calc R U . . .
C28 C 0.4612(3) 0.2332(3) 0.0123(2) 0.0364(6) Uani 1 1 d . . . . .
H28 H 0.550(3) 0.1886(16) 0.0106(3) 0.044 Uiso 1 1 calc R U . . .
C7 C -0.2067(3) 0.1138(3) 0.6715(3) 0.0425(7) Uani 1 1 d . . . . .
H7 H -0.2135(4) 0.1292(7) 0.601(3) 0.051 Uiso 1 1 calc R U . . .
C8 C -0.0759(2) 0.2965(2) 0.4374(2) 0.0268(5) Uani 1 1 d . . . . .
C30 C 0.2690(3) 0.2893(2) -0.0488(2) 0.0371(6) Uani 1 1 d . . . . .
H30 H 0.2283(17) 0.2849(3) -0.0901(17) 0.045 Uiso 1 1 calc R U . . .
C27 C 0.3965(2) 0.3040(2) 0.0804(2) 0.0308(5) Uani 1 1 d . . . . .
H27 H 0.4383(15) 0.3079(3) 0.1224(15) 0.037 Uiso 1 1 calc R U . . .
C21 C 0.3797(2) 0.3311(2) 0.4048(2) 0.0278(5) Uani 1 1 d . . . . .
H21 H 0.3832(3) 0.266(2) 0.470(2) 0.033 Uiso 1 1 calc R U . . .
C29 C 0.3979(3) 0.2269(2) -0.0532(2) 0.0347(6) Uani 1 1 d . . . . .
H29 H 0.4431(17) 0.1797(17) -0.1012(18) 0.042 Uiso 1 1 calc R U . . .
C33 C 0.0698(3) 0.7026(2) 0.0663(2) 0.0361(6) Uani 1 1 d . . . . .
H33 H -0.011(3) 0.6873(6) 0.139(2) 0.043 Uiso 1 1 calc R U . . .
C4 C -0.1888(3) 0.0700(2) 0.8873(2) 0.0349(6) Uani 1 1 d . . . . .
H4 H -0.1851(3) 0.0575(6) 0.956(3) 0.042 Uiso 1 1 calc R U . . .
C9 C -0.1732(3) 0.4009(3) 0.4356(3) 0.0399(6) Uani 1 1 d . . . . .
H9 H -0.2003(11) 0.4318(12) 0.495(2) 0.048 Uiso 1 1 calc R U . . .
C36 C 0.2828(3) 0.7438(3) -0.1270(3) 0.0435(7) Uani 1 1 d . . . . .
H36 H 0.3557 0.7578 -0.1934 0.052 Uiso 1 1 calc R U . . .
C34 C 0.0658(4) 0.8134(3) -0.0155(3) 0.0480(8) Uani 1 1 d . . . . .
H34 H -0.014(3) 0.878(3) -0.0055(5) 0.058 Uiso 1 1 calc R U . . .
C35 C 0.1734(4) 0.8344(3) -0.1121(3) 0.0495(9) Uani 1 1 d . . . . .
H35 H 0.1714(4) 0.909(3) -0.167(2) 0.059 Uiso 1 1 calc R U . . .
C5 C -0.2789(3) 0.0308(3) 0.8773(3) 0.0408(7) Uani 1 1 d . . . . .
H5 H -0.333(2) -0.0107(17) 0.943(3) 0.049 Uiso 1 1 calc R U . . .
C10 C -0.2294(3) 0.4586(3) 0.3446(3) 0.0497(8) Uani 1 1 d . . . . .
H10 H -0.292(3) 0.528(3) 0.3416(3) 0.060 Uiso 1 1 calc R U . . .
C6 C -0.2892(4) 0.0526(3) 0.7703(3) 0.0527(9) Uani 1 1 d . . . . .
H6 H -0.352(3) 0.0262(12) 0.7645(4) 0.063 Uiso 1 1 calc R U . . .
O2 O 0.5096(10) 0.3023(9) 0.6254(9) 0.062(4) Uani 0.284(9) 1 d D . P . .
H210 H 0.575(9) 0.244(7) 0.650(13) 0.074 Uiso 0.284(9) 1 d D U P . .
H211 H 0.459(11) 0.265(9) 0.626(13) 0.074 Uiso 0.284(9) 1 d D U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P2 C32 1.829(2) . ?
P2 C26 1.829(2) . ?
P2 C25 1.844(2) . ?
P1 C2 1.784(2) . ?
P1 C14 1.784(2) . ?
P1 C8 1.789(2) . ?
P1 C1 1.831(3) . ?
O1 C19 1.384(3) . ?
O1 C20 1.393(3) . ?
C14 C15 1.395(3) . ?
C14 C19 1.398(3) . ?
C11 C12 1.376(5) . ?
C11 C10 1.377(5) . ?
C11 H11 1.01(4) . ?
C22 C21 1.386(4) . ?
C22 C23 1.393(4) . ?
C22 H22 0.94(3) . ?
C2 C7 1.390(4) . ?
C2 C3 1.396(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.95(3) . ?
C13 C8 1.387(4) . ?
C13 C12 1.397(4) . ?
C13 H13 0.92(3) . ?
C19 C18 1.383(3) . ?
C25 C24 1.394(3) . ?
C25 C20 1.394(3) . ?
C16 C17 1.384(4) . ?
C16 H16 0.86(3) . ?
C1 F1 1.376(3) . ?
C1 H1A 0.94(2) . ?
C1 H1B 0.94(2) . ?
C20 C21 1.391(3) . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C12 H12 0.90(4) . ?
C32 C37 1.388(4) . ?
C32 C33 1.400(4) . ?
C23 C24 1.387(4) . ?
C23 H23 0.93(3) . ?
C24 H24 0.92(3) . ?
C26 C31 1.390(3) . ?
C26 C27 1.393(3) . ?
C18 H18 0.85(3) . ?
C37 C36 1.394(4) . ?
C37 H37 0.94(3) . ?
C3 C4 1.391(4) . ?
C3 H3 0.95(3) . ?
C31 C30 1.393(4) . ?
C31 H31 0.93(3) . ?
C28 C29 1.381(4) . ?
C28 C27 1.388(4) . ?
C28 H28 0.96(3) . ?
C7 C6 1.388(4) . ?
C7 H7 0.91(4) . ?
C8 C9 1.397(4) . ?
C30 C29 1.381(4) . ?
C30 H30 0.88(4) . ?
C27 H27 0.90(3) . ?
C21 H21 0.92(3) . ?
C29 H29 0.95(3) . ?
C33 C34 1.380(4) . ?
C33 H33 1.05(3) . ?
C4 C5 1.375(4) . ?
C4 H4 0.89(3) . ?
C9 C10 1.391(4) . ?
C9 H9 0.94(4) . ?
C36 C35 1.379(5) . ?
C36 H36 0.9500 . ?
C34 C35 1.393(5) . ?
C34 H34 0.99(4) . ?
C35 H35 0.93(4) . ?
C5 C6 1.383(5) . ?
C5 H5 0.92(4) . ?
C10 H10 0.92(4) . ?
C6 H6 0.94(4) . ?
O2 H210 0.89(2) . ?
O2 H211 0.88(2) . ?

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
C32 P2 C26 100.64(11) . . ?
C32 P2 C25 102.25(10) . . ?
C26 P2 C25 101.36(10) . . ?
C2 P1 C14 109.47(11) . . ?
C2 P1 C8 110.11(11) . . ?
C14 P1 C8 111.40(11) . . ?
C2 P1 C1 108.60(12) . . ?
C14 P1 C1 107.17(11) . . ?
C8 P1 C1 110.00(12) . . ?
C19 O1 C20 121.65(18) . . ?
C15 C14 C19 119.3(2) . . ?
C15 C14 P1 122.18(17) . . ?
C19 C14 P1 118.49(16) . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C21 C22 C23 120.3(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C7 C2 C3 120.4(2) . . ?
C7 C2 P1 119.50(19) . . ?
C3 C2 P1 120.02(19) . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C8 C13 C12 119.2(3) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C18 C19 O1 123.6(2) . . ?
C18 C19 C14 121.1(2) . . ?
O1 C19 C14 115.1(2) . . ?
C24 C25 C20 117.0(2) . . ?
C24 C25 P2 126.39(17) . . ?
C20 C25 P2 116.31(17) . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
F1 C1 P1 109.29(17) . . ?
F1 C1 H1A 109.8 . . ?
P1 C1 H1A 109.8 . . ?
F1 C1 H1B 109.8 . . ?
P1 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C21 C20 O1 122.5(2) . . ?
C21 C20 C25 123.1(2) . . ?
O1 C20 C25 114.22(19) . . ?
C18 C17 C16 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C37 C32 C33 119.0(2) . . ?
C37 C32 P2 124.93(19) . . ?
C33 C32 P2 116.04(19) . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 121.2(2) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C31 C26 C27 118.6(2) . . ?
C31 C26 P2 116.71(18) . . ?
C27 C26 P2 124.68(19) . . ?
C17 C18 C19 118.7(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C32 C37 C36 120.3(3) . . ?
C32 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C26 C31 C30 120.5(2) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C29 C28 C27 120.2(3) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C6 C7 C2 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
C13 C8 C9 120.8(2) . . ?
C13 C8 P1 120.50(19) . . ?
C9 C8 P1 118.7(2) . . ?
C29 C30 C31 120.1(3) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C28 C27 C26 120.7(3) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C22 C21 C20 118.2(2) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C30 C29 C28 119.8(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C34 C33 C32 120.5(3) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C35 C36 C37 120.2(3) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C33 C34 C35 120.0(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 119.9(3) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
H210 O2 H211 103(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 P1 C14 C15 3.8(2) . . . . ?
C8 P1 C14 C15 -118.2(2) . . . . ?
C1 P1 C14 C15 121.4(2) . . . . ?
C2 P1 C14 C19 -174.92(18) . . . . ?
C8 P1 C14 C19 63.1(2) . . . . ?
C1 P1 C14 C19 -57.3(2) . . . . ?
C14 P1 C2 C7 -95.3(2) . . . . ?
C8 P1 C2 C7 27.5(3) . . . . ?
C1 P1 C2 C7 148.0(2) . . . . ?
C14 P1 C2 C3 82.4(2) . . . . ?
C8 P1 C2 C3 -154.8(2) . . . . ?
C1 P1 C2 C3 -34.3(2) . . . . ?
C19 C14 C15 C16 0.1(3) . . . . ?
P1 C14 C15 C16 -178.56(18) . . . . ?
C20 O1 C19 C18 -53.0(3) . . . . ?
C20 O1 C19 C14 132.3(2) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
P1 C14 C19 C18 178.82(18) . . . . ?
C15 C14 C19 O1 174.9(2) . . . . ?
P1 C14 C19 O1 -6.3(3) . . . . ?
C32 P2 C25 C24 2.2(2) . . . . ?
C26 P2 C25 C24 105.8(2) . . . . ?
C32 P2 C25 C20 176.02(18) . . . . ?
C26 P2 C25 C20 -80.30(19) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C2 P1 C1 F1 -50.7(2) . . . . ?
C14 P1 C1 F1 -168.89(17) . . . . ?
C8 P1 C1 F1 69.9(2) . . . . ?
C19 O1 C20 C21 -29.9(3) . . . . ?
C19 O1 C20 C25 155.6(2) . . . . ?
C24 C25 C20 C21 1.1(3) . . . . ?
P2 C25 C20 C21 -173.36(19) . . . . ?
C24 C25 C20 O1 175.6(2) . . . . ?
P2 C25 C20 O1 1.1(3) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C8 C13 C12 C11 1.6(4) . . . . ?
C26 P2 C32 C37 -33.2(2) . . . . ?
C25 P2 C32 C37 71.1(2) . . . . ?
C26 P2 C32 C33 145.4(2) . . . . ?
C25 P2 C32 C33 -110.4(2) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C20 C25 C24 C23 0.0(3) . . . . ?
P2 C25 C24 C23 173.8(2) . . . . ?
C32 P2 C26 C31 -76.5(2) . . . . ?
C25 P2 C26 C31 178.59(19) . . . . ?
C32 P2 C26 C27 103.5(2) . . . . ?
C25 P2 C26 C27 -1.4(2) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
O1 C19 C18 C17 -174.4(2) . . . . ?
C14 C19 C18 C17 0.0(4) . . . . ?
C33 C32 C37 C36 1.6(4) . . . . ?
P2 C32 C37 C36 -179.9(2) . . . . ?
C7 C2 C3 C4 -0.6(4) . . . . ?
P1 C2 C3 C4 -178.3(2) . . . . ?
C27 C26 C31 C30 -2.6(4) . . . . ?
P2 C26 C31 C30 177.3(2) . . . . ?
C3 C2 C7 C6 -0.7(5) . . . . ?
P1 C2 C7 C6 177.0(3) . . . . ?
C12 C13 C8 C9 -0.9(4) . . . . ?
C12 C13 C8 P1 179.46(19) . . . . ?
C2 P1 C8 C13 -105.1(2) . . . . ?
C14 P1 C8 C13 16.6(2) . . . . ?
C1 P1 C8 C13 135.2(2) . . . . ?
C2 P1 C8 C9 75.3(2) . . . . ?
C14 P1 C8 C9 -163.1(2) . . . . ?
C1 P1 C8 C9 -44.4(2) . . . . ?
C26 C31 C30 C29 1.6(4) . . . . ?
C29 C28 C27 C26 0.3(4) . . . . ?
C31 C26 C27 C28 1.7(4) . . . . ?
P2 C26 C27 C28 -178.3(2) . . . . ?
C23 C22 C21 C20 0.7(4) . . . . ?
O1 C20 C21 C22 -175.4(2) . . . . ?
C25 C20 C21 C22 -1.4(4) . . . . ?
C31 C30 C29 C28 0.5(4) . . . . ?
C27 C28 C29 C30 -1.4(4) . . . . ?
C37 C32 C33 C34 -1.2(4) . . . . ?
P2 C32 C33 C34 -179.8(2) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C13 C8 C9 C10 -0.4(4) . . . . ?
P1 C8 C9 C10 179.2(2) . . . . ?
C32 C37 C36 C35 -0.5(4) . . . . ?
C32 C33 C34 C35 -0.2(5) . . . . ?
C37 C36 C35 C34 -0.9(4) . . . . ?
C33 C34 C35 C36 1.2(5) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?
C12 C11 C10 C9 -0.6(5) . . . . ?
C8 C9 C10 C11 1.2(5) . . . . ?
C4 C5 C6 C7 0.7(5) . . . . ?
C2 C7 C6 C5 0.7(5) . . . . ?

_refine_diff_density_max         2.846
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.094

_shelxl_version_number           2014-3

