# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_TRIAL2
_database_code_depnum_ccdc_archive 'CCDC 1024970'
_audit_update_record             
;
2014-09-18 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H27 N6 O4 P'
_chemical_formula_weight         530.51

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'
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'

_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_H-M_alt        'P -3'
_space_group_name_Hall           '-P 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   16.08(2)
_cell_length_b                   16.08(2)
_cell_length_c                   6.269(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1404(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2612
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.77

_exptl_crystal_description       needle
_exptl_crystal_colour            colurless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5613
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart Apex Duo'
_diffrn_measurement_method       'Omega and Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14052
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_av_R_equivalents  0.1479
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.122
_diffrn_reflns_theta_max         28.112
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             2194
_reflns_number_gt                1426
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1859P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2194
_refine_ls_number_parameters     121
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0863
_refine_ls_wR_factor_ref         0.2874
_refine_ls_wR_factor_gt          0.2637
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
P1 P 0.6667 0.3333 0.4591(3) 0.0226(4) Uani 1 3 d S T P . .
O1 O 0.6667 0.3333 0.6990(7) 0.0258(9) Uani 1 3 d S T P . .
N1 N 0.6165(2) 0.3930(2) 0.3577(5) 0.0263(7) Uani 1 1 d . . . . .
H1 H 0.6493 0.4361 0.2593 0.032 Uiso 1 1 calc R U . . .
C11 C 0.5254(2) 0.3811(2) 0.4145(6) 0.0261(8) Uani 1 1 d . . . . .
C12 C 0.4814(3) 0.4158(3) 0.2675(6) 0.0285(8) Uani 1 1 d . . . . .
H12 H 0.5157 0.4465 0.1413 0.034 Uiso 1 1 calc R U . . .
N13 N 0.3960(2) 0.4077(2) 0.2964(5) 0.0320(8) Uani 1 1 d . . . . .
C14 C 0.3451(3) 0.3619(3) 0.4784(6) 0.0291(8) Uani 1 1 d . . . . .
C15 C 0.3837(3) 0.3277(3) 0.6368(6) 0.0281(8) Uani 1 1 d . . . . .
C16 C 0.4767(3) 0.3390(3) 0.6018(6) 0.0286(8) Uani 1 1 d . . . . .
H16 H 0.5049 0.3178 0.7062 0.034 Uiso 1 1 calc R U . . .
C17 C 0.3283(3) 0.2818(3) 0.8231(7) 0.0358(9) Uani 1 1 d . . . . .
H17 H 0.3538 0.2591 0.9304 0.043 Uiso 1 1 calc R U . . .
C18 C 0.2379(3) 0.2704(4) 0.8470(8) 0.0451(11) Uani 1 1 d . . . . .
H18 H 0.2017 0.2406 0.9719 0.054 Uiso 1 1 calc R U . . .
C19 C 0.1986(3) 0.3031(4) 0.6858(8) 0.0472(12) Uani 1 1 d . . . . .
H19 H 0.1357 0.2935 0.7024 0.057 Uiso 1 1 calc R U . . .
C20 C 0.2512(3) 0.3484(3) 0.5059(8) 0.0422(10) Uani 1 1 d . . . . .
H20 H 0.2247 0.3708 0.4001 0.051 Uiso 1 1 calc R U . . .
O1S O 0.5113(2) 0.1897(2) 0.9527(5) 0.0350(7) Uani 1 1 d D . . . .
H1S H 0.479(4) 0.136(4) 0.881(8) 0.052 Uiso 1 1 d D U . . .
H2S H 0.557(4) 0.226(4) 0.862(8) 0.052 Uiso 1 1 d D 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 1.504(5) . ?
P1 N1 1.658(4) 2_655 ?
P1 N1 1.658(4) 3_665 ?
P1 N1 1.658(4) . ?
N1 C11 1.424(5) . ?
N1 H1 0.8800 . ?
C11 C16 1.385(5) . ?
C11 C12 1.434(5) . ?
C12 N13 1.326(5) . ?
C12 H12 0.9500 . ?
N13 C14 1.383(5) . ?
C14 C15 1.419(5) . ?
C14 C20 1.424(6) . ?
C15 C17 1.430(5) . ?
C15 C16 1.431(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.425(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(7) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
O1S H1S 0.88(4) . ?
O1S H2S 0.88(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
O1 P1 N1 112.56(12) . 2_655 ?
O1 P1 N1 112.56(12) . 3_665 ?
N1 P1 N1 106.22(14) 2_655 3_665 ?
O1 P1 N1 112.56(12) . . ?
N1 P1 N1 106.22(14) 2_655 . ?
N1 P1 N1 106.22(14) 3_665 . ?
C11 N1 P1 126.2(2) . . ?
C11 N1 H1 116.9 . . ?
P1 N1 H1 116.9 . . ?
C16 C11 N1 124.7(3) . . ?
C16 C11 C12 117.8(3) . . ?
N1 C11 C12 117.5(3) . . ?
N13 C12 C11 124.3(4) . . ?
N13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C12 N13 C14 118.2(3) . . ?
N13 C14 C15 121.8(3) . . ?
N13 C14 C20 118.7(4) . . ?
C15 C14 C20 119.5(4) . . ?
C14 C15 C17 119.4(3) . . ?
C14 C15 C16 118.4(3) . . ?
C17 C15 C16 122.2(3) . . ?
C11 C16 C15 119.4(3) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C15 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C15 C17 H17 120.0 . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C14 120.1(4) . . ?
C19 C20 H20 119.9 . . ?
C14 C20 H20 119.9 . . ?
H1S O1S H2S 102(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1S 0.88 2.06 2.876(5) 154.5 3_664
O1S H1S N13 0.88(4) 2.06(4) 2.938(5) 177(6) 5_556
O1S H2S O1 0.88(4) 2.02(4) 2.887(5) 167(6) .

_refine_diff_density_max         0.733
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.125

_shelxl_version_number           2013-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_preparation       Luminescent
