# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1042193'
_audit_update_record             
;
2015-01-06 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N2 O2 P'
_chemical_formula_weight         414.42

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6861(19)
_cell_length_b                   11.136(2)
_cell_length_c                   12.338(3)
_cell_angle_alpha                113.11(3)
_cell_angle_beta                 95.32(3)
_cell_angle_gamma                113.21(3)
_cell_volume                     1075.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10572
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         27.51
_reflns_number_total             4885
_reflns_number_gt                2956
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0977P)²+0.0000P] 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         4885
_refine_ls_number_parameters     272
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1706
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.010
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.12683(7) 0.40217(6) 0.20449(5) 0.0498(2) Uani 1 1 d . . .
C24 C -0.0180(3) 0.2596(3) 0.4017(2) 0.0722(7) Uani 1 1 d . . .
H24A H -0.0170 0.3455 0.4001 0.108 Uiso 1 1 calc R . .
H24B H 0.0432 0.2875 0.4813 0.108 Uiso 1 1 calc R . .
H24C H -0.1242 0.1882 0.3853 0.108 Uiso 1 1 calc R . .
O1 O -0.00786(19) 0.4290(2) 0.18145(17) 0.0733(5) Uani 1 1 d . . .
C23 C 0.2450(4) 0.4993(3) -0.0216(3) 0.0745(8) Uani 1 1 d . . .
H23A H 0.2076 0.5503 0.0411 0.112 Uiso 1 1 calc R . .
H23B H 0.1727 0.4565 -0.1011 0.112 Uiso 1 1 calc R . .
H23C H 0.3463 0.5680 -0.0178 0.112 Uiso 1 1 calc R . .
C22 C 0.2875(2) 0.5622(2) 0.33319(19) 0.0467(5) Uani 1 1 d . . .
N2 N 0.0485(2) 0.1955(2) 0.30820(16) 0.0536(5) Uani 1 1 d . . .
C21 C 0.2032(3) 0.3365(2) 0.08035(19) 0.0504(5) Uani 1 1 d . . .
N1 N 0.2575(2) 0.3833(2) -0.00217(17) 0.0571(5) Uani 1 1 d . . .
C20 C 0.1364(3) 0.0459(2) 0.18482(19) 0.0514(5) Uani 1 1 d . . .
C19 C 0.2178(2) 0.2136(2) 0.06569(19) 0.0496(5) Uani 1 1 d . . .
C18 C 0.4255(3) 0.5613(3) 0.3716(3) 0.0716(7) Uani 1 1 d . . .
H18A H 0.4370 0.4772 0.3310 0.086 Uiso 1 1 calc R . .
C17 C 0.1000(3) 0.2459(2) 0.2268(2) 0.0509(5) Uani 1 1 d . . .
C16 C 0.1562(2) 0.1592(2) 0.15134(19) 0.0496(5) Uani 1 1 d . . .
C15 C 0.0240(3) -0.0216(3) 0.3362(2) 0.0672(7) Uani 1 1 d . . .
H15A H -0.0236 -0.0046 0.3987 0.081 Uiso 1 1 calc R . .
C14 C 0.3961(4) 0.8121(3) 0.4938(2) 0.0732(8) Uani 1 1 d . . .
H14A H 0.3862 0.8971 0.5347 0.088 Uiso 1 1 calc R . .
C13 C 0.2730(3) 0.6878(3) 0.3948(2) 0.0584(6) Uani 1 1 d . . .
H13A H 0.1804 0.6895 0.3700 0.070 Uiso 1 1 calc R . .
C12 C 0.5300(4) 0.8095(3) 0.5305(3) 0.0790(9) Uani 1 1 d . . .
H12A H 0.6117 0.8926 0.5973 0.095 Uiso 1 1 calc R . .
C11 C 0.1648(3) -0.0768(3) 0.1439(2) 0.0642(6) Uani 1 1 d . . .
H11A H 0.2103 -0.0971 0.0802 0.077 Uiso 1 1 calc R . .
C10 C 0.0543(4) -0.1385(3) 0.2935(3) 0.0779(8) Uani 1 1 d . . .
H10A H 0.0273 -0.2020 0.3282 0.093 Uiso 1 1 calc R . .
C9 C 0.2854(3) 0.1787(2) -0.03224(19) 0.0550(6) Uani 1 1 d . . .
C8 C 0.0673(3) 0.0717(2) 0.2824(2) 0.0536(6) Uani 1 1 d . . .
C7 C 0.3069(3) 0.2866(3) -0.0726(2) 0.0596(6) Uani 1 1 d . . .
C6 C 0.3324(3) 0.0714(3) -0.0895(2) 0.0671(7) Uani 1 1 d . . .
H6A H 0.3203 0.0003 -0.0643 0.081 Uiso 1 1 calc R . .
C5 C 0.1246(4) -0.1661(3) 0.1992(3) 0.0773(8) Uani 1 1 d . . .
H5A H 0.1447 -0.2464 0.1733 0.093 Uiso 1 1 calc R . .
C4 C 0.3687(3) 0.2844(3) -0.1712(2) 0.0756(8) Uani 1 1 d . . .
H4A H 0.3796 0.3532 -0.1990 0.091 Uiso 1 1 calc R . .
C3 C 0.3968(4) 0.0735(3) -0.1838(3) 0.0851(9) Uani 1 1 d . . .
H3A H 0.4308 0.0043 -0.2213 0.102 Uiso 1 1 calc R . .
O2 O -0.2233(4) 0.4705(4) 0.2989(3) 0.1402(11) Uani 1 1 d D . .
H1 H -0.1380 0.4566 0.2549 0.27(3) Uiso 1 1 d RD . .
C2 C 0.5469(4) 0.6862(3) 0.4706(3) 0.0884(10) Uani 1 1 d . . .
H2A H 0.6401 0.6860 0.4963 0.106 Uiso 1 1 calc R . .
C1 C 0.4121(4) 0.1779(4) -0.2248(3) 0.0880(10) Uani 1 1 d . . .
H1A H 0.4532 0.1742 -0.2905 0.106 Uiso 1 1 calc R . .
C26 C -0.3504(6) 0.3334(6) 0.2480(5) 0.1459(19) Uani 1 1 d D . .
H2C H -0.3256 0.2581 0.2019 0.219 Uiso 1 1 d RD . .
H2B H -0.4314 0.3196 0.1907 0.219 Uiso 1 1 d RD . .
H2D H -0.3949 0.3069 0.3013 0.219 Uiso 1 1 d RD . .


_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 1.4755(18) . ?
P1 C21 1.785(2) . ?
P1 C17 1.791(2) . ?
P1 C22 1.804(3) . ?
C24 N2 1.452(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 N1 1.451(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22 C13 1.377(3) . ?
C22 C18 1.381(3) . ?
N2 C17 1.373(3) . ?
N2 C8 1.378(3) . ?
C21 N1 1.373(3) . ?
C21 C19 1.373(3) . ?
N1 C7 1.375(3) . ?
C20 C11 1.406(3) . ?
C20 C8 1.417(3) . ?
C20 C16 1.426(3) . ?
C19 C9 1.421(3) . ?
C19 C16 1.474(3) . ?
C18 C2 1.386(4) . ?
C18 H18A 0.9300 . ?
C17 C16 1.377(3) . ?
C15 C10 1.360(4) . ?
C15 C8 1.395(3) . ?
C15 H15A 0.9300 . ?
C14 C12 1.349(4) . ?
C14 C13 1.390(4) . ?
C14 H14A 0.9300 . ?
C13 H13A 0.9300 . ?
C12 C2 1.364(5) . ?
C12 H12A 0.9300 . ?
C11 C5 1.372(4) . ?
C11 H11A 0.9300 . ?
C10 C5 1.393(4) . ?
C10 H10A 0.9300 . ?
C9 C6 1.399(4) . ?
C9 C7 1.424(4) . ?
C7 C4 1.401(3) . ?
C6 C3 1.374(4) . ?
C6 H6A 0.9300 . ?
C5 H5A 0.9300 . ?
C4 C1 1.360(4) . ?
C4 H4A 0.9300 . ?
C3 C1 1.403(5) . ?
C3 H3A 0.9300 . ?
O2 C26 1.365(5) . ?
O2 H1 1.0578 . ?
C2 H2A 0.9300 . ?
C1 H1A 0.9300 . ?
C26 H2C 0.9464 . ?
C26 H2B 0.9247 . ?
C26 H2D 0.9000 . ?

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 C21 119.07(11) . . ?
O1 P1 C17 120.07(11) . . ?
C21 P1 C17 88.77(11) . . ?
O1 P1 C22 111.41(11) . . ?
C21 P1 C22 108.38(10) . . ?
C17 P1 C22 106.68(11) . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 C22 C18 119.1(2) . . ?
C13 C22 P1 119.64(18) . . ?
C18 C22 P1 121.26(18) . . ?
C17 N2 C8 107.60(19) . . ?
C17 N2 C24 125.7(2) . . ?
C8 N2 C24 126.7(2) . . ?
N1 C21 C19 111.4(2) . . ?
N1 C21 P1 134.98(19) . . ?
C19 C21 P1 113.55(17) . . ?
C21 N1 C7 106.4(2) . . ?
C21 N1 C23 126.3(2) . . ?
C7 N1 C23 126.8(2) . . ?
C11 C20 C8 118.0(2) . . ?
C11 C20 C16 136.2(2) . . ?
C8 C20 C16 105.7(2) . . ?
C21 C19 C9 106.9(2) . . ?
C21 C19 C16 112.26(19) . . ?
C9 C19 C16 140.8(2) . . ?
C22 C18 C2 119.8(3) . . ?
C22 C18 H18A 120.1 . . ?
C2 C18 H18A 120.1 . . ?
N2 C17 C16 110.2(2) . . ?
N2 C17 P1 135.89(18) . . ?
C16 C17 P1 113.60(17) . . ?
C17 C16 C20 107.3(2) . . ?
C17 C16 C19 111.6(2) . . ?
C20 C16 C19 141.1(2) . . ?
C10 C15 C8 117.3(3) . . ?
C10 C15 H15A 121.3 . . ?
C8 C15 H15A 121.3 . . ?
C12 C14 C13 120.0(3) . . ?
C12 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C22 C13 C14 120.3(3) . . ?
C22 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C14 C12 C2 120.7(3) . . ?
C14 C12 H12A 119.7 . . ?
C2 C12 H12A 119.7 . . ?
C5 C11 C20 119.1(3) . . ?
C5 C11 H11A 120.5 . . ?
C20 C11 H11A 120.5 . . ?
C15 C10 C5 122.0(3) . . ?
C15 C10 H10A 119.0 . . ?
C5 C10 H10A 119.0 . . ?
C6 C9 C19 135.4(2) . . ?
C6 C9 C7 119.2(2) . . ?
C19 C9 C7 105.4(2) . . ?
N2 C8 C15 128.5(2) . . ?
N2 C8 C20 109.1(2) . . ?
C15 C8 C20 122.3(2) . . ?
N1 C7 C4 128.8(3) . . ?
N1 C7 C9 109.8(2) . . ?
C4 C7 C9 121.4(3) . . ?
C3 C6 C9 118.5(3) . . ?
C3 C6 H6A 120.7 . . ?
C9 C6 H6A 120.7 . . ?
C11 C5 C10 121.2(3) . . ?
C11 C5 H5A 119.4 . . ?
C10 C5 H5A 119.4 . . ?
C1 C4 C7 117.5(3) . . ?
C1 C4 H4A 121.2 . . ?
C7 C4 H4A 121.2 . . ?
C6 C3 C1 121.3(3) . . ?
C6 C3 H3A 119.4 . . ?
C1 C3 H3A 119.4 . . ?
C26 O2 H1 105.9 . . ?
C12 C2 C18 120.2(3) . . ?
C12 C2 H2A 119.9 . . ?
C18 C2 H2A 119.9 . . ?
C4 C1 C3 122.0(3) . . ?
C4 C1 H1A 119.0 . . ?
C3 C1 H1A 119.0 . . ?
O2 C26 H2C 111.9 . . ?
O2 C26 H2B 113.8 . . ?
H2C C26 H2B 102.9 . . ?
O2 C26 H2D 116.0 . . ?
H2C C26 H2D 105.7 . . ?
H2B C26 H2D 105.4 . . ?

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
O2 H1 O1 1.06 1.67 2.732(4) 178.0 .

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 1052683'
_audit_update_record             
;
2015-03-07 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N2 O2 P'
_chemical_formula_weight         428.45

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.649(2)
_cell_length_b                   10.083(2)
_cell_length_c                   20.878(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.74(3)
_cell_angle_gamma                90.00
_cell_volume                     2202.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20088
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0407
_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       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5024
_reflns_number_gt                3529
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1027P)²+0.0000P] 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         5024
_refine_ls_number_parameters     296
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1681
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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 0.78932(5) 0.74261(5) 0.10529(3) 0.03687(17) Uani 1 1 d . . .
N1 N 0.66786(16) 0.98785(17) -0.03461(8) 0.0402(4) Uani 1 1 d . . .
N2 N 0.94874(16) 1.07175(16) 0.07065(9) 0.0404(4) Uani 1 1 d . . .
O1 O 0.83229(15) 0.60315(15) 0.10038(8) 0.0526(4) Uani 1 1 d . . .
C1 C 0.3826(3) 0.8045(3) -0.11871(15) 0.0729(8) Uani 1 1 d . . .
H1A H 0.3149 0.8080 -0.1540 0.087 Uiso 1 1 calc R . .
C2 C 0.4691(2) 0.9080(3) -0.10884(13) 0.0606(7) Uani 1 1 d . . .
H2A H 0.4612 0.9805 -0.1368 0.073 Uiso 1 1 calc R . .
C3 C 0.5686(2) 0.8990(2) -0.05523(10) 0.0440(5) Uani 1 1 d . . .
C4 C 0.58207(18) 0.7898(2) -0.01252(10) 0.0407(5) Uani 1 1 d . . .
C5 C 0.4924(2) 0.6867(2) -0.02411(13) 0.0532(6) Uani 1 1 d . . .
H5A H 0.4989 0.6137 0.0035 0.064 Uiso 1 1 calc R . .
C6 C 0.3939(2) 0.6957(3) -0.07758(15) 0.0682(8) Uani 1 1 d . . .
H6A H 0.3343 0.6275 -0.0860 0.082 Uiso 1 1 calc R . .
C7 C 0.6791(2) 1.1144(2) -0.06699(12) 0.0524(6) Uani 1 1 d . . .
H7A H 0.7526 1.1613 -0.0444 0.079 Uiso 1 1 calc R . .
H7B H 0.6037 1.1664 -0.0666 0.079 Uiso 1 1 calc R . .
H7C H 0.6882 1.0987 -0.1112 0.079 Uiso 1 1 calc R . .
C8 C 0.74316(18) 0.93536(19) 0.01956(9) 0.0359(4) Uani 1 1 d . . .
C9 C 0.69397(18) 0.8140(2) 0.03475(10) 0.0382(4) Uani 1 1 d . . .
C10 C 0.86215(18) 0.97014(19) 0.06378(9) 0.0359(4) Uani 1 1 d . . .
C11 C 0.9429(3) 1.1958(3) 0.03488(15) 0.0594(7) Uani 1 1 d . . .
C12 C 1.04650(19) 1.0411(2) 0.12249(10) 0.0411(5) Uani 1 1 d . . .
C13 C 1.1570(2) 1.1118(3) 0.14773(13) 0.0562(6) Uani 1 1 d . . .
H13A H 1.1747 1.1932 0.1305 0.067 Uiso 1 1 calc R . .
C14 C 1.2387(2) 1.0554(3) 0.19927(14) 0.0650(7) Uani 1 1 d . . .
H14A H 1.3139 1.0999 0.2166 0.078 Uiso 1 1 calc R . .
C15 C 1.2136(2) 0.9350(3) 0.22650(13) 0.0634(7) Uani 1 1 d . . .
H15A H 1.2714 0.9010 0.2616 0.076 Uiso 1 1 calc R . .
C16 C 1.1041(2) 0.8652(3) 0.20211(11) 0.0543(6) Uani 1 1 d . . .
H16A H 1.0868 0.7849 0.2206 0.065 Uiso 1 1 calc R . .
C17 C 1.01965(18) 0.9179(2) 0.14904(10) 0.0406(5) Uani 1 1 d . . .
C18 C 0.90131(18) 0.8740(2) 0.11066(10) 0.0387(4) Uani 1 1 d . . .
C19 C 0.70399(18) 0.76282(19) 0.17120(10) 0.0380(4) Uani 1 1 d . . .
C20 C 0.6105(2) 0.6710(2) 0.17777(12) 0.0528(6) Uani 1 1 d . . .
H20A H 0.5961 0.5985 0.1498 0.063 Uiso 1 1 calc R . .
C21 C 0.5381(2) 0.6870(3) 0.22612(14) 0.0625(7) Uani 1 1 d . . .
H21A H 0.4755 0.6251 0.2305 0.075 Uiso 1 1 calc R . .
C22 C 0.5585(2) 0.7933(3) 0.26735(12) 0.0568(6) Uani 1 1 d . . .
H22A H 0.5093 0.8040 0.2994 0.068 Uiso 1 1 calc R . .
C23 C 0.6523(2) 0.8850(3) 0.26154(11) 0.0539(6) Uani 1 1 d . . .
H23A H 0.6659 0.9576 0.2895 0.065 Uiso 1 1 calc R . .
C24 C 0.7255(2) 0.8686(2) 0.21417(10) 0.0454(5) Uani 1 1 d . . .
H24A H 0.7899 0.9292 0.2110 0.054 Uiso 1 1 calc R . .
O2 O 1.06472(19) 0.4724(2) 0.12152(12) 0.0783(7) Uani 1 1 d D . .
C26 C 1.1453(4) 0.5515(4) 0.0937(3) 0.1200(17) Uani 1 1 d D . .
H26A H 1.1661 0.6291 0.1211 0.144 Uiso 1 1 calc R . .
H26B H 1.0989 0.5820 0.0519 0.144 Uiso 1 1 calc R . .
C25 C 1.2579(4) 0.4947(5) 0.0841(2) 0.1180(15) Uani 1 1 d . . .
H25A H 1.3066 0.5588 0.0651 0.177 Uiso 1 1 calc R . .
H25B H 1.2393 0.4200 0.0554 0.177 Uiso 1 1 calc R . .
H25C H 1.3063 0.4657 0.1252 0.177 Uiso 1 1 calc R . .
H2B H 0.995(3) 0.517(4) 0.1199(18) 0.092(11) Uiso 1 1 d . . .
H11B H 0.860(3) 1.244(3) 0.0332(16) 0.096(11) Uiso 1 1 d D . .
H11A H 1.000(3) 1.254(3) 0.0566(15) 0.085(10) Uiso 1 1 d D . .
H11C H 0.949(3) 1.184(3) -0.0069(16) 0.097(11) Uiso 1 1 d 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 O1 1.4882(15) . ?
P1 C18 1.772(2) . ?
P1 C9 1.778(2) . ?
P1 C19 1.796(2) . ?
N1 C8 1.365(2) . ?
N1 C3 1.391(3) . ?
N1 C7 1.459(3) . ?
N2 C10 1.368(3) . ?
N2 C12 1.390(3) . ?
N2 C11 1.452(3) . ?
C1 C2 1.382(4) . ?
C1 C6 1.384(5) . ?
C2 C3 1.393(3) . ?
C3 C4 1.407(3) . ?
C4 C5 1.402(3) . ?
C4 C9 1.420(3) . ?
C5 C6 1.385(4) . ?
C8 C9 1.390(3) . ?
C8 C10 1.465(3) . ?
C10 C18 1.385(3) . ?
C12 C13 1.393(3) . ?
C12 C17 1.411(3) . ?
C13 C14 1.374(4) . ?
C14 C15 1.388(4) . ?
C15 C16 1.376(3) . ?
C16 C17 1.396(3) . ?
C17 C18 1.432(3) . ?
C19 C24 1.385(3) . ?
C19 C20 1.385(3) . ?
C20 C21 1.389(3) . ?
C21 C22 1.367(4) . ?
C22 C23 1.382(4) . ?
C23 C24 1.379(3) . ?
O2 C26 1.376(3) . ?
C26 C25 1.377(5) . ?

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 C18 119.93(9) . . ?
O1 P1 C9 117.46(10) . . ?
C18 P1 C9 91.33(9) . . ?
O1 P1 C19 111.46(9) . . ?
C18 P1 C19 107.29(10) . . ?
C9 P1 C19 107.24(9) . . ?
C8 N1 C3 107.58(17) . . ?
C8 N1 C7 129.54(19) . . ?
C3 N1 C7 122.86(19) . . ?
C10 N2 C12 107.91(16) . . ?
C10 N2 C11 128.88(19) . . ?
C12 N2 C11 123.12(19) . . ?
C2 C1 C6 121.8(3) . . ?
C1 C2 C3 117.2(3) . . ?
N1 C3 C2 128.8(2) . . ?
N1 C3 C4 109.00(18) . . ?
C2 C3 C4 122.2(2) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 C9 134.8(2) . . ?
C3 C4 C9 106.22(18) . . ?
C6 C5 C4 118.7(3) . . ?
C1 C6 C5 121.2(3) . . ?
N1 C8 C9 109.99(17) . . ?
N1 C8 C10 137.30(18) . . ?
C9 C8 C10 112.67(17) . . ?
C8 C9 C4 107.20(18) . . ?
C8 C9 P1 111.35(15) . . ?
C4 C9 P1 141.45(16) . . ?
N2 C10 C18 109.96(18) . . ?
N2 C10 C8 137.11(18) . . ?
C18 C10 C8 112.90(17) . . ?
N2 C12 C13 129.7(2) . . ?
N2 C12 C17 108.95(18) . . ?
C13 C12 C17 121.4(2) . . ?
C14 C13 C12 116.9(3) . . ?
C13 C14 C15 122.7(2) . . ?
C16 C15 C14 120.7(3) . . ?
C15 C16 C17 118.4(3) . . ?
C16 C17 C12 120.0(2) . . ?
C16 C17 C18 134.2(2) . . ?
C12 C17 C18 105.89(18) . . ?
C10 C18 C17 107.28(18) . . ?
C10 C18 P1 111.58(15) . . ?
C17 C18 P1 141.10(16) . . ?
C24 C19 C20 119.06(19) . . ?
C24 C19 P1 122.52(15) . . ?
C20 C19 P1 118.39(17) . . ?
C19 C20 C21 120.0(2) . . ?
C22 C21 C20 120.3(2) . . ?
C21 C22 C23 120.2(2) . . ?
C24 C23 C22 119.8(2) . . ?
C23 C24 C19 120.7(2) . . ?
O2 C26 C25 116.7(3) . . ?

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
O2 H2B O1 0.86(3) 1.91(4) 2.766(3) 170(4) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.061
