# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_nany
_database_code_depnum_ccdc_archive 'CCDC 1496180'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;
_audit_creation_date             2016-06-23
_audit_creation_method           
;
  Olex2 1.1
  (compiled Sep 28 2011 20:36:17, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'F6 P, C5.5 H12 N2 O0.5'
_chemical_formula_sum            'C5.50 H12 F6 N2 O0.50 P'
_chemical_formula_weight         259.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.155(3)
_cell_length_b                   6.7318(13)
_cell_length_c                   19.587(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.09(3)
_cell_angle_gamma                90.00
_cell_volume                     2013.0(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    22857
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      3.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.642018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.1192 before and 0.0806 after correction.
The Ratio of minimum to maximum transmission is 0.6420.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22857
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.017
_diffrn_reflns_theta_min         3.307
_diffrn_ambient_temperature      200.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaAPEXII'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2623
_reflns_number_total             2935
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0725P)²+3.7103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1557
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 P1, F2B, F1, F4A, F5A, F3B, F1A, F2A, F4B, F5B, F2, F3A, F1B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
P1 \\sim F2B \\sim F1 \\sim F4A \\sim F5A \\sim F3B \\sim F1A \\sim F2A \\sim
F4B \\sim F5B \\sim F2 \\sim F3A \\sim F1B: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
4. Others
 Sof(F3B)=Sof(F1B)=Sof(F4B)=Sof(F2B)=Sof(F1)=Sof(F5B)=1-FVAR(1)
 Sof(F2)=Sof(F1A)=Sof(F2A)=Sof(F4A)=Sof(F3A)=Sof(F5A)=FVAR(1)
5.a Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.33600(3) 0.16291(8) 0.39342(3) 0.03479(17) Uani 1 1 d U . .
N2 N 0.48997(9) 0.5577(2) 0.32878(7) 0.0248(3) Uani 1 1 d . . .
O1 O 0.5000 0.1019(3) 0.2500 0.0370(4) Uani 1 2 d S . .
F3B F 0.2941(5) -0.0309(9) 0.3534(5) 0.099(2) Uani 0.385(5) 1 d PU A 2
N1 N 0.59759(9) 0.3123(2) 0.37339(7) 0.0269(3) Uani 1 1 d . . .
C6 C 0.40009(11) 0.6039(3) 0.28231(10) 0.0309(3) Uani 1 1 d . . .
H6A H 0.4013 0.7134 0.2513 0.046 Uiso 1 1 calc R . .
H6B H 0.3652 0.6386 0.3119 0.046 Uiso 1 1 calc R . .
H6C H 0.3752 0.4898 0.2535 0.046 Uiso 1 1 calc R . .
C1 C 0.53131(10) 0.3928(2) 0.32217(8) 0.0221(3) Uani 1 1 d . . .
C2 C 0.5000 0.2802(3) 0.2500 0.0234(4) Uani 1 2 d S . .
F1B F 0.2676(4) 0.2894(11) 0.3254(4) 0.115(3) Uani 0.385(5) 1 d PU A 2
C3 C 0.66091(12) 0.1728(3) 0.35979(12) 0.0373(4) Uani 1 1 d . . .
H3A H 0.6499 0.0412 0.3736 0.056 Uiso 1 1 calc R . .
H3B H 0.7193 0.2122 0.3876 0.056 Uiso 1 1 calc R . .
H3C H 0.6547 0.1744 0.3093 0.056 Uiso 1 1 calc R . .
C5 C 0.52777(15) 0.7123(3) 0.38296(11) 0.0384(4) Uani 1 1 d . . .
H5A H 0.5122 0.8409 0.3614 0.058 Uiso 1 1 calc R . .
H5B H 0.5904 0.6992 0.4004 0.058 Uiso 1 1 calc R . .
H5C H 0.5054 0.6978 0.4225 0.058 Uiso 1 1 calc R . .
C4 C 0.61442(16) 0.3484(3) 0.45091(10) 0.0437(5) Uani 1 1 d . . .
H4A H 0.6618 0.4413 0.4684 0.066 Uiso 1 1 calc R . .
H4B H 0.6298 0.2256 0.4769 0.066 Uiso 1 1 calc R . .
H4C H 0.5627 0.4019 0.4579 0.066 Uiso 1 1 calc R . .
F4B F 0.3980(5) 0.1635(9) 0.3443(5) 0.078(2) Uani 0.385(5) 1 d PU A 2
F2B F 0.4017(6) 0.0606(11) 0.4504(4) 0.121(3) Uani 0.385(5) 1 d PU A 2
F1 F 0.2737(9) 0.1828(13) 0.4357(8) 0.161(5) Uani 0.385(5) 1 d PU A 2
F5B F 0.3775(5) 0.3797(12) 0.4187(4) 0.0649(18) Uani 0.385(5) 1 d PU A 2
F2 F 0.3342(3) 0.1336(5) 0.47524(14) 0.0739(12) Uani 0.615(5) 1 d PU A 1
F1A F 0.23418(18) 0.1481(6) 0.3695(2) 0.0846(13) Uani 0.615(5) 1 d PU A 1
F2A F 0.4396(2) 0.1636(7) 0.4252(4) 0.123(2) Uani 0.615(5) 1 d PU A 1
F4A F 0.3415(5) 0.1799(7) 0.3181(2) 0.118(2) Uani 0.615(5) 1 d PU A 1
F3A F 0.3404(3) -0.0784(4) 0.3903(2) 0.0628(9) Uani 0.615(5) 1 d PU A 1
F5A F 0.3337(3) 0.3909(6) 0.4044(3) 0.0728(13) Uani 0.615(5) 1 d PU A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F3B 1.559(5) . ?
P1 F1B 1.661(6) . ?
P1 F4B 1.599(5) . ?
P1 F2B 1.440(6) . ?
P1 F1 1.505(5) . ?
P1 F5B 1.615(7) . ?
P1 F2 1.625(3) . ?
P1 F1A 1.559(3) . ?
P1 F2A 1.584(3) . ?
P1 F4A 1.510(3) . ?
P1 F3A 1.628(3) . ?
P1 F5A 1.552(4) . ?
N2 C6 1.473(2) . ?
N2 C1 1.324(2) . ?
N2 C5 1.469(2) . ?
O1 C2 1.201(3) . ?
N1 C1 1.321(2) . ?
N1 C3 1.475(2) . ?
N1 C4 1.473(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C1 C2 1.5366(19) . ?
C2 C1 1.5366(19) 2_655 ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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
F3B P1 F1B 87.7(4) . . ?
F3B P1 F4B 87.4(4) . . ?
F3B P1 F5B 168.4(4) . . ?
F4B P1 F1B 84.2(4) . . ?
F4B P1 F5B 84.5(4) . . ?
F2B P1 F3B 94.5(5) . . ?
F2B P1 F1B 174.8(5) . . ?
F2B P1 F4B 91.1(5) . . ?
F2B P1 F1 94.1(7) . . ?
F2B P1 F5B 93.9(4) . . ?
F1 P1 F3B 95.3(5) . . ?
F1 P1 F1B 90.4(7) . . ?
F1 P1 F4B 173.9(5) . . ?
F1 P1 F5B 92.1(5) . . ?
F5B P1 F1B 83.3(4) . . ?
F2 P1 F3A 86.02(18) . . ?
F1A P1 F2 86.0(2) . . ?
F1A P1 F2A 173.6(3) . . ?
F1A P1 F3A 88.82(19) . . ?
F2A P1 F2 88.3(3) . . ?
F2A P1 F3A 88.0(2) . . ?
F4A P1 F2 176.6(3) . . ?
F4A P1 F1A 96.0(4) . . ?
F4A P1 F2A 89.6(4) . . ?
F4A P1 F3A 91.3(2) . . ?
F4A P1 F5A 94.1(3) . . ?
F5A P1 F2 88.5(2) . . ?
F5A P1 F1A 92.0(2) . . ?
F5A P1 F2A 90.7(3) . . ?
F5A P1 F3A 174.4(2) . . ?
C1 N2 C6 122.93(14) . . ?
C1 N2 C5 124.11(15) . . ?
C5 N2 C6 112.95(15) . . ?
C1 N1 C3 124.18(15) . . ?
C1 N1 C4 123.08(16) . . ?
C4 N1 C3 112.72(16) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C1 C2 118.61(13) . . ?
N1 C1 N2 125.43(14) . . ?
N1 C1 C2 115.94(14) . . ?
O1 C2 C1 119.55(9) . 2_655 ?
O1 C2 C1 119.56(9) . . ?
C1 C2 C1 120.89(19) . 2_655 ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

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


