# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1406404'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;
_chemical_name_systematic        'tris(4-cyanatophenyl) phosphate '
_chemical_name_common            PhosCy3
_chemical_formula_moiety         'C21 H12 N3 O7 P'
_chemical_formula_sum            'C21 H12 N3 O7 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         449.31
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      trigonal
_space_group_name_H-M_alt        'P 3 1 c'
_space_group_name_Hall           'P 3 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, z+1/2'

_cell_length_a                   12.5995(9)
_cell_length_b                   12.5995(9)
_cell_length_c                   7.5587(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1039.16(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6378
_cell_measurement_theta_min      2.6947
_cell_measurement_theta_max      27.1518
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.192
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460

_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       'profile data from omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            12418
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measured_fraction_theta_full 1.001
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             1431
_reflns_number_gt                1378
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0591
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_number_reflns         1431
_refine_ls_number_parameters     113
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²+0.2150P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.108
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 662 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(3)

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.3333 0.6667 0.99518(14) 0.0413(2) Uani d T P S 1 . .
O O2 0.39714(15) 0.60188(15) 1.0887(2) 0.0512(4) Uani d . . . 1 . .
O O1 0.3333 0.6667 0.8032(4) 0.0495(7) Uani d T P S 1 . .
C C1 0.5084(2) 0.6112(2) 1.0348(3) 0.0416(5) Uani d . . . 1 . .
O O3 0.8264(2) 0.6105(2) 0.9122(4) 0.0787(6) Uani d . . . 1 . .
C C3 0.6256(3) 0.5121(3) 1.0217(4) 0.0551(6) Uani d . . . 1 . .
C C5 0.7118(2) 0.7198(2) 0.9217(4) 0.0502(6) Uani d . . . 1 . .
C C4 0.7192(2) 0.6167(3) 0.9521(3) 0.0511(6) Uani d . . . 1 . .
C C2 0.5174(2) 0.5083(2) 1.0640(3) 0.0504(6) Uani d . . . 1 . .
C C6 0.6034(2) 0.7171(2) 0.9651(3) 0.0477(6) Uani d . . . 1 . .
N N1 0.9990(3) 0.7710(4) 0.7602(6) 0.1043(12) Uani d . . . 1 . .
C C7 0.9167(3) 0.6999(4) 0.8321(5) 0.0743(9) Uani d . . . 1 . .
H H4 0.593(2) 0.789(3) 0.949(3) 0.048(7) Uiso d . . . 1 . .
H H3 0.781(3) 0.792(3) 0.876(4) 0.060(8) Uiso d . . . 1 . .
H H2 0.631(3) 0.446(3) 1.039(4) 0.070(9) Uiso d . . . 1 . .
H H1 0.451(3) 0.438(3) 1.118(4) 0.052(7) Uiso d . . . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
P1 0.0375(3) 0.0375(3) 0.0488(5) 0.01876(14) 0 0
O2 0.0466(9) 0.0493(9) 0.0603(10) 0.0258(8) 0.0062(7) 0.0103(8)
O1 0.0483(10) 0.0483(10) 0.0518(16) 0.0242(5) 0 0
C1 0.0409(11) 0.0416(11) 0.0452(12) 0.0227(10) -0.0048(9) -0.0020(9)
O3 0.0600(13) 0.0872(15) 0.1086(17) 0.0516(12) 0.0019(11) 0.0003(13)
C3 0.0647(17) 0.0488(14) 0.0653(16) 0.0386(13) -0.0080(13) -0.0009(12)
C5 0.0422(12) 0.0454(13) 0.0599(14) 0.0194(11) -0.0014(11) -0.0003(11)
C4 0.0476(13) 0.0605(16) 0.0548(14) 0.0341(13) -0.0109(10) -0.0100(11)
C2 0.0574(15) 0.0385(12) 0.0548(13) 0.0235(12) -0.0033(12) 0.0029(11)
C6 0.0479(14) 0.0391(12) 0.0599(15) 0.0246(11) -0.0024(11) 0.0017(10)
N1 0.0568(17) 0.133(3) 0.114(2) 0.040(2) 0.0054(17) -0.014(2)
C7 0.0500(16) 0.098(3) 0.082(2) 0.0425(18) -0.0098(16) -0.0188(18)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . 1.451(3) ?
P1 O2 2_665 1.5710(17) ?
P1 O2 3_565 1.5710(17) ?
P1 O2 . 1.5710(17) ?
O2 C1 . 1.407(3) ?
C1 C6 . 1.376(3) ?
C1 C2 . 1.375(3) ?
O3 C7 . 1.284(5) ?
O3 C4 . 1.424(3) ?
C3 C4 . 1.361(4) ?
C3 C2 . 1.378(4) ?
C5 C4 . 1.367(4) ?
C5 C6 . 1.389(4) ?
N1 C7 . 1.116(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 O2 . 2_665 116.73(8) ?
O1 P1 O2 . 3_565 116.73(8) ?
O2 P1 O2 2_665 3_565 101.34(9) ?
O1 P1 O2 . . 116.73(8) ?
O2 P1 O2 2_665 . 101.34(9) ?
O2 P1 O2 3_565 . 101.34(9) ?
C1 O2 P1 . . 125.01(15) ?
C6 C1 C2 . . 122.3(2) ?
C6 C1 O2 . . 122.6(2) ?
C2 C1 O2 . . 115.1(2) ?
C7 O3 C4 . . 119.9(3) ?
C4 C3 C2 . . 119.1(2) ?
C4 C5 C6 . . 118.0(2) ?
C5 C4 C3 . . 123.2(2) ?
C5 C4 O3 . . 122.3(3) ?
C3 C4 O3 . . 114.5(2) ?
C3 C2 C1 . . 118.5(2) ?
C1 C6 C5 . . 118.9(2) ?
N1 C7 O3 . . 173.9(4) ?

_shelx_res_file                  
;
TITL TG_AC48_85B_1_0m in P-31c
CELL  0.71073  12.5995  12.5995   7.5587   90.000   90.000  120.000
ZERR  2.00 0.0009 0.0009 0.0005 0.000 0.000 0.000
LATT -1
SYMM -Y, X-Y, Z
SYMM -X+Y, -X, Z
SYMM Y, X, 1/2+Z
SYMM X-Y, -Y, 1/2+Z
SYMM -X, -X+Y, 1/2+Z
SFAC C  N  O  P  H
UNIT 42  6  14  2  24
L.S. 75
SHEL 999 0.8
ACTA
BOND
FMAP 2
PLAN 1
SIZE 0.192 0.225 0.425
TEMP 23.000
WGHT    0.023600    0.215000
FVAR       0.66162
P1    4    0.333333    0.666667    0.995177    10.33333    0.03752    0.03752 =
         0.04884    0.00000    0.00000    0.01876
O2    3    0.397143    0.601882    1.088655    11.00000    0.04661    0.04926 =
         0.06032    0.01031    0.00622    0.02581
O1    3    0.333333    0.666667    0.803167    10.33333    0.04834    0.04834 =
         0.05177    0.00000    0.00000    0.02417
C1    1    0.508361    0.611181    1.034788    11.00000    0.04092    0.04156 =
         0.04523   -0.00197   -0.00479    0.02269
O3    3    0.826438    0.610462    0.912235    11.00000    0.05999    0.08721 =
         0.10859    0.00033    0.00187    0.05157
C3    1    0.625563    0.512057    1.021740    11.00000    0.06475    0.04880 =
         0.06525   -0.00095   -0.00805    0.03862
C5    1    0.711847    0.719820    0.921681    11.00000    0.04216    0.04537 =
         0.05989   -0.00030   -0.00141    0.01940
C4    1    0.719202    0.616731    0.952081    11.00000    0.04757    0.06046 =
         0.05478   -0.00997   -0.01089    0.03407
C2    1    0.517365    0.508257    1.064024    11.00000    0.05737    0.03850 =
         0.05480    0.00293   -0.00325    0.02348
C6    1    0.603367    0.717078    0.965058    11.00000    0.04794    0.03905 =
         0.05989    0.00170   -0.00241    0.02463
N1    2    0.999031    0.771008    0.760250    11.00000    0.05676    0.13292 =
         0.11361   -0.01352    0.00536    0.04016
C7    1    0.916682    0.699927    0.832115    11.00000    0.04998    0.09844 =
         0.08167   -0.01880   -0.00977    0.04253
H4    5    0.592913    0.788687    0.949028    11.00000    0.04764
H3    5    0.781035    0.791835    0.875895    11.00000    0.06017
H2    5    0.631363    0.445558    1.039253    11.00000    0.06987
H1    5    0.450651    0.437566    1.117814    11.00000    0.05195
HKLF 4

REM  TG_AC48_85B_1_0m in P-31c
REM R1 =  0.0255 for    1378 Fo > 4sig(Fo)  and  0.0270 for all    1431 data
REM    113 parameters refined using      1 restraints

END

WGHT      0.0368      0.1179

REM Highest difference peak  0.147,  deepest hole -0.108,  1-sigma level  0.028
Q1    1   0.3721  0.6221  0.9994  11.00000  0.05    0.15
;
_shelx_res_checksum              80085
