# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_BD269_a
_database_code_depnum_ccdc_archive 'CCDC 1935968'
loop_
_audit_author_name
_audit_author_address
'Blazej Dziuk'
;Opole University
Poland
;
_audit_update_record             
;
2019-06-23 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 N O5 P'
_chemical_formula_weight         313.28

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'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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                   10.7418(3)
_cell_length_b                   10.0430(2)
_cell_length_c                   14.6765(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.329(3)
_cell_angle_gamma                90
_cell_volume                     1534.04(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    10172
_cell_measurement_theta_min      3.375
_cell_measurement_theta_max      25.993

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(1)
_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  Xcalibur
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_reflns_number            10172
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.375
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2987
_reflns_number_gt                2459
_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       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2987
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.50761(3) 0.98631(3) 0.23504(2) 0.01291(11) Uani 1 1 d . . . . .
O1 O 0.21046(8) 0.71102(8) 0.35949(6) 0.0155(2) Uani 1 1 d . . . . .
N1 N 0.32166(10) 0.85907(10) 0.30037(8) 0.0138(2) Uani 1 1 d . . . . .
H1 H 0.3608 0.7891 0.2881 0.017 Uiso 1 1 calc R U . . .
C1 C 0.11550(13) 0.68106(13) 0.41193(10) 0.0190(3) Uani 1 1 d . . . . .
H1A H 0.0316 0.7135 0.3783 0.023 Uiso 1 1 calc R U . . .
H1B H 0.1388 0.7233 0.4732 0.023 Uiso 1 1 calc R U . . .
O2 O 0.16424(9) 0.92914(9) 0.37088(6) 0.0188(2) Uani 1 1 d . . . . .
C2 C 0.11287(12) 0.53268(13) 0.42240(10) 0.0157(3) Uani 1 1 d . . . . .
O3 O 0.54002(9) 1.12041(9) 0.20855(7) 0.0188(2) Uani 1 1 d . . . . .
C3 C 0.17551(12) 0.47243(13) 0.50682(9) 0.0168(3) Uani 1 1 d . . . . .
H3 H 0.2190 0.5245 0.5571 0.020 Uiso 1 1 calc R U . . .
C4 C 0.17325(13) 0.33483(13) 0.51622(10) 0.0184(3) Uani 1 1 d . . . . .
H4 H 0.2152 0.2951 0.5727 0.022 Uiso 1 1 calc R U . . .
O4 O 0.61442(9) 0.91981(9) 0.31608(6) 0.0170(2) Uani 1 1 d . . . . .
C5 C 0.10882(13) 0.25672(14) 0.44174(10) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.1082 0.1646 0.4479 0.023 Uiso 1 1 calc R U . . .
O5 O 0.48361(8) 0.87841(9) 0.15551(6) 0.0157(2) Uani 1 1 d . . . . .
C6 C 0.04528(13) 0.31618(14) 0.35793(10) 0.0202(3) Uani 1 1 d . . . . .
H6 H 0.0011 0.2639 0.3080 0.024 Uiso 1 1 calc R U . . .
C7 C 0.04744(13) 0.45357(14) 0.34827(10) 0.0184(3) Uani 1 1 d . . . . .
H7 H 0.0048 0.4929 0.2918 0.022 Uiso 1 1 calc R U . . .
C8 C 0.22670(12) 0.84258(12) 0.34578(9) 0.0130(3) Uani 1 1 d . . . . .
C9 C 0.36014(12) 0.98329(12) 0.27206(9) 0.0124(3) Uani 1 1 d . . . . .
C10 C 0.29974(13) 1.09906(13) 0.27104(9) 0.0172(3) Uani 1 1 d . . . . .
H10A H 0.2237 1.1033 0.2904 0.021 Uiso 1 1 calc R U . . .
H10B H 0.3335 1.1757 0.2509 0.021 Uiso 1 1 calc R U . . .
C11 C 0.69474(13) 1.00231(13) 0.38926(10) 0.0201(3) Uani 1 1 d . . . . .
H11A H 0.7011 0.9621 0.4503 0.024 Uiso 1 1 calc R U . . .
H11B H 0.6562 1.0897 0.3890 0.024 Uiso 1 1 calc R U . . .
C12 C 0.82652(13) 1.01579(15) 0.37224(11) 0.0263(3) Uani 1 1 d . . . . .
H12A H 0.8621 0.9289 0.3682 0.040 Uiso 1 1 calc R U . . .
H12B H 0.8810 1.0642 0.4232 0.040 Uiso 1 1 calc R U . . .
H12C H 0.8207 1.0629 0.3144 0.040 Uiso 1 1 calc R U . . .
C13 C 0.57077(13) 0.87032(13) 0.09261(9) 0.0162(3) Uani 1 1 d . . . . .
H13A H 0.6561 0.8439 0.1277 0.019 Uiso 1 1 calc R U . . .
H13B H 0.5768 0.9562 0.0638 0.019 Uiso 1 1 calc R U . . .
C14 C 0.51595(14) 0.76842(14) 0.01866(10) 0.0207(3) Uani 1 1 d . . . . .
H14A H 0.4277 0.7895 -0.0099 0.031 Uiso 1 1 calc R U . . .
H14B H 0.5211 0.6818 0.0471 0.031 Uiso 1 1 calc R U . . .
H14C H 0.5640 0.7688 -0.0285 0.031 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 O3 1.4673(9) . ?
P1 O5 1.5666(9) . ?
P1 O4 1.5816(9) . ?
P1 C9 1.7977(13) . ?
O1 C8 1.3542(15) . ?
O1 C1 1.4532(15) . ?
N1 C8 1.3597(16) . ?
N1 C9 1.4088(16) . ?
N1 H1 0.8600 . ?
C1 C2 1.4991(18) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O2 C8 1.2099(15) . ?
C2 C7 1.3894(19) . ?
C2 C3 1.3933(18) . ?
C3 C4 1.3896(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.3838(19) . ?
C4 H4 0.9300 . ?
O4 C11 1.4579(15) . ?
C5 C6 1.386(2) . ?
C5 H5 0.9300 . ?
O5 C13 1.4707(14) . ?
C6 C7 1.3879(18) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C10 1.3296(17) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 C12 1.5032(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.5019(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O3 P1 O5 116.33(5) . . ?
O3 P1 O4 114.28(5) . . ?
O5 P1 O4 102.90(5) . . ?
O3 P1 C9 112.34(6) . . ?
O5 P1 C9 102.63(5) . . ?
O4 P1 C9 107.16(5) . . ?
C8 O1 C1 114.44(10) . . ?
C8 N1 C9 124.25(11) . . ?
C8 N1 H1 117.9 . . ?
C9 N1 H1 117.9 . . ?
O1 C1 C2 107.07(10) . . ?
O1 C1 H1A 110.3 . . ?
C2 C1 H1A 110.3 . . ?
O1 C1 H1B 110.3 . . ?
C2 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
C7 C2 C3 119.17(13) . . ?
C7 C2 C1 120.45(12) . . ?
C3 C2 C1 120.38(12) . . ?
C4 C3 C2 120.25(12) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.20(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C11 O4 P1 120.06(8) . . ?
C4 C5 C6 119.81(13) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C13 O5 P1 119.53(8) . . ?
C5 C6 C7 120.15(13) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.43(13) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
O2 C8 O1 123.66(12) . . ?
O2 C8 N1 126.98(12) . . ?
O1 C8 N1 109.36(10) . . ?
C10 C9 N1 126.85(12) . . ?
C10 C9 P1 116.47(10) . . ?
N1 C9 P1 116.67(9) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
O4 C11 C12 109.80(11) . . ?
O4 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
O4 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
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 . . ?
O5 C13 C14 107.14(10) . . ?
O5 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O5 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C8 O1 C1 C2 -178.57(10) . . . . ?
O1 C1 C2 C7 -78.83(15) . . . . ?
O1 C1 C2 C3 101.51(14) . . . . ?
C7 C2 C3 C4 0.54(19) . . . . ?
C1 C2 C3 C4 -179.79(12) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
O3 P1 O4 C11 32.10(11) . . . . ?
O5 P1 O4 C11 159.15(9) . . . . ?
C9 P1 O4 C11 -93.06(10) . . . . ?
C3 C4 C5 C6 -0.69(19) . . . . ?
O3 P1 O5 C13 43.69(11) . . . . ?
O4 P1 O5 C13 -82.04(9) . . . . ?
C9 P1 O5 C13 166.76(9) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C3 C2 C7 C6 -0.48(19) . . . . ?
C1 C2 C7 C6 179.86(12) . . . . ?
C1 O1 C8 O2 -3.16(18) . . . . ?
C1 O1 C8 N1 177.01(10) . . . . ?
C9 N1 C8 O2 -2.2(2) . . . . ?
C9 N1 C8 O1 177.62(11) . . . . ?
C8 N1 C9 C10 -11.3(2) . . . . ?
C8 N1 C9 P1 167.72(10) . . . . ?
O3 P1 C9 C10 0.06(13) . . . . ?
O5 P1 C9 C10 -125.65(11) . . . . ?
O4 P1 C9 C10 126.38(10) . . . . ?
O3 P1 C9 N1 -179.06(9) . . . . ?
O5 P1 C9 N1 55.24(10) . . . . ?
O4 P1 C9 N1 -52.74(10) . . . . ?
P1 O4 C11 C12 -104.59(11) . . . . ?
P1 O5 C13 C14 -174.30(9) . . . . ?

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 O3 0.86 2.00 2.8401(14) 166.9 2_645
C10 H10A O2 0.93 2.29 2.8695(16) 120.1 .
C14 H14A O1 0.96 2.63 3.5318(17) 157.0 4_575

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_BD334_a
_database_code_depnum_ccdc_archive 'CCDC 1935969'
loop_
_audit_author_name
_audit_author_address
'Blazej Dziuk'
;Opole University
Poland
;
_audit_update_record             
;
2019-06-23 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H25 N2 O6 P'
_chemical_formula_weight         336.32

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'
N N 0.0061 0.0033 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.9692(3)
_cell_length_b                   17.6005(5)
_cell_length_c                   10.3762(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.329(4)
_cell_angle_gamma                90
_cell_volume                     1695.94(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    11346
_cell_measurement_theta_min      2.689
_cell_measurement_theta_max      25.999

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_reflns_number            11346
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.689
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3315
_reflns_number_gt                2510
_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       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0395P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3315
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_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 0.66965(4) 0.55185(2) 0.88490(4) 0.01332(10) Uani 1 1 d . . . . .
N1 N -0.01473(12) 0.55228(7) 0.62433(12) 0.0159(3) Uani 1 1 d . . . . .
H1 H -0.0715 0.5139 0.5967 0.019 Uiso 1 1 calc R U . . .
N2 N 0.38052(12) 0.55328(6) 0.76092(11) 0.0130(3) Uani 1 1 d . . . . .
H2 H 0.3896 0.5478 0.8461 0.016 Uiso 1 1 calc R U . . .
O1 O -0.18137(11) 0.61644(6) 0.46070(10) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.00335(11) 0.68062(6) 0.62146(11) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.21550(10) 0.56699(6) 0.54211(10) 0.0166(2) Uani 1 1 d . . . . .
O4 O 0.64797(11) 0.50605(6) 0.99336(10) 0.0198(2) Uani 1 1 d . . . . .
O5 O 0.72006(10) 0.63430(6) 0.93639(10) 0.0178(2) Uani 1 1 d . . . . .
O6 O 0.79018(10) 0.52345(5) 0.83253(10) 0.0157(2) Uani 1 1 d . . . . .
C1 C -0.24954(16) 0.68428(8) 0.37909(15) 0.0186(3) Uani 1 1 d . . . . .
C2 C -0.14916(19) 0.72123(10) 0.31817(18) 0.0304(4) Uani 1 1 d . . . . .
H2A H -0.1157 0.6838 0.2696 0.046 Uiso 1 1 calc R U . . .
H2B H -0.0684 0.7428 0.3911 0.046 Uiso 1 1 calc R U . . .
H2C H -0.1996 0.7606 0.2551 0.046 Uiso 1 1 calc R U . . .
C3 C -0.29664(18) 0.73937(9) 0.46675(16) 0.0247(4) Uani 1 1 d . . . . .
H3A H -0.3529 0.7793 0.4092 0.037 Uiso 1 1 calc R U . . .
H3B H -0.2133 0.7608 0.5368 0.037 Uiso 1 1 calc R U . . .
H3C H -0.3536 0.7129 0.5097 0.037 Uiso 1 1 calc R U . . .
C4 C -0.37956(17) 0.65015(9) 0.26665(16) 0.0274(4) Uani 1 1 d . . . . .
H4A H -0.4358 0.6900 0.2088 0.041 Uiso 1 1 calc R U . . .
H4B H -0.4371 0.6232 0.3083 0.041 Uiso 1 1 calc R U . . .
H4C H -0.3480 0.6157 0.2118 0.041 Uiso 1 1 calc R U . . .
C5 C -0.05840(15) 0.62223(9) 0.57278(15) 0.0174(3) Uani 1 1 d . . . . .
C6 C 0.12772(15) 0.54260(9) 0.72589(14) 0.0162(3) Uani 1 1 d . . . . .
H6A H 0.1370 0.4915 0.7632 0.019 Uiso 1 1 calc R U . . .
H6B H 0.1415 0.5779 0.8014 0.019 Uiso 1 1 calc R U . . .
C7 C 0.24470(15) 0.55580(8) 0.66567(14) 0.0136(3) Uani 1 1 d . . . . .
C8 C 0.50808(15) 0.55879(8) 0.73260(14) 0.0134(3) Uani 1 1 d . . . . .
C9 C 0.51906(16) 0.56995(8) 0.60988(15) 0.0168(3) Uani 1 1 d . . . . .
H9A H 0.4364 0.5750 0.5311 0.020 Uiso 1 1 calc R U . . .
H9B H 0.6094 0.5727 0.6030 0.020 Uiso 1 1 calc R U . . .
C10 C 0.75614(18) 0.69034(9) 0.85081(16) 0.0254(4) Uani 1 1 d . . . . .
H10A H 0.6738 0.6992 0.7665 0.030 Uiso 1 1 calc R U . . .
H10B H 0.8353 0.6721 0.8259 0.030 Uiso 1 1 calc R U . . .
C11 C 0.79806(19) 0.76241(9) 0.93185(17) 0.0302(4) Uani 1 1 d . . . . .
H11A H 0.8237 0.7999 0.8777 0.045 Uiso 1 1 calc R U . . .
H11B H 0.8789 0.7530 1.0155 0.045 Uiso 1 1 calc R U . . .
H11C H 0.7185 0.7806 0.9544 0.045 Uiso 1 1 calc R U . . .
C12 C 0.78788(16) 0.44422(8) 0.78935(15) 0.0192(3) Uani 1 1 d . . . . .
H12A H 0.7856 0.4420 0.6952 0.023 Uiso 1 1 calc R U . . .
H12B H 0.7023 0.4192 0.7922 0.023 Uiso 1 1 calc R U . . .
C13 C 0.91919(17) 0.40470(9) 0.88419(16) 0.0235(4) Uani 1 1 d . . . . .
H13A H 0.9188 0.3529 0.8552 0.035 Uiso 1 1 calc R U . . .
H13B H 0.9197 0.4059 0.9768 0.035 Uiso 1 1 calc R U . . .
H13C H 1.0036 0.4299 0.8815 0.035 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 O4 1.4629(10) . ?
P1 O5 1.5649(10) . ?
P1 O6 1.5696(10) . ?
P1 C8 1.8042(14) . ?
N1 C5 1.3498(18) . ?
N1 C6 1.4379(18) . ?
N1 H1 0.8600 . ?
N2 C7 1.3560(17) . ?
N2 C8 1.4089(17) . ?
N2 H2 0.8600 . ?
O1 C5 1.3522(17) . ?
O1 C1 1.4785(17) . ?
O2 C5 1.2099(17) . ?
O3 C7 1.2230(16) . ?
O5 C10 1.4571(17) . ?
O6 C12 1.4623(17) . ?
C1 C2 1.511(2) . ?
C1 C3 1.516(2) . ?
C1 C4 1.517(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 C7 1.5279(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.3316(19) . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C10 C11 1.495(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.493(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
O4 P1 O5 111.55(6) . . ?
O4 P1 O6 115.90(6) . . ?
O5 P1 O6 102.84(5) . . ?
O4 P1 C8 112.12(6) . . ?
O5 P1 C8 108.05(6) . . ?
O6 P1 C8 105.68(6) . . ?
C5 N1 C6 119.26(12) . . ?
C5 N1 H1 120.4 . . ?
C6 N1 H1 120.4 . . ?
C7 N2 C8 125.70(12) . . ?
C7 N2 H2 117.2 . . ?
C8 N2 H2 117.2 . . ?
C5 O1 C1 121.05(11) . . ?
C10 O5 P1 122.64(9) . . ?
C12 O6 P1 118.76(9) . . ?
O1 C1 C2 110.53(12) . . ?
O1 C1 C3 110.55(12) . . ?
C2 C1 C3 111.86(13) . . ?
O1 C1 C4 101.93(11) . . ?
C2 C1 C4 111.05(13) . . ?
C3 C1 C4 110.49(13) . . ?
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 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 N1 124.57(14) . . ?
O2 C5 O1 125.98(14) . . ?
N1 C5 O1 109.44(12) . . ?
N1 C6 C7 112.30(11) . . ?
N1 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O3 C7 N2 124.28(13) . . ?
O3 C7 C6 121.81(12) . . ?
N2 C7 C6 113.91(12) . . ?
C9 C8 N2 127.15(13) . . ?
C9 C8 P1 119.33(11) . . ?
N2 C8 P1 113.49(10) . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
O5 C10 C11 108.17(12) . . ?
O5 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O5 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C12 C13 109.27(12) . . ?
O6 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
O6 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O4 P1 O5 C10 176.90(11) . . . . ?
O6 P1 O5 C10 52.03(12) . . . . ?
C8 P1 O5 C10 -59.44(13) . . . . ?
O4 P1 O6 C12 51.58(11) . . . . ?
O5 P1 O6 C12 173.55(9) . . . . ?
C8 P1 O6 C12 -73.24(11) . . . . ?
C5 O1 C1 C2 61.35(17) . . . . ?
C5 O1 C1 C3 -63.06(17) . . . . ?
C5 O1 C1 C4 179.46(12) . . . . ?
C6 N1 C5 O2 -13.2(2) . . . . ?
C6 N1 C5 O1 167.57(11) . . . . ?
C1 O1 C5 O2 3.9(2) . . . . ?
C1 O1 C5 N1 -176.89(11) . . . . ?
C5 N1 C6 C7 -68.01(17) . . . . ?
C8 N2 C7 O3 -3.7(2) . . . . ?
C8 N2 C7 C6 175.79(12) . . . . ?
N1 C6 C7 O3 -5.60(19) . . . . ?
N1 C6 C7 N2 174.88(12) . . . . ?
C7 N2 C8 C9 2.5(2) . . . . ?
C7 N2 C8 P1 -179.20(11) . . . . ?
O4 P1 C8 C9 -152.90(11) . . . . ?
O5 P1 C8 C9 83.77(13) . . . . ?
O6 P1 C8 C9 -25.76(13) . . . . ?
O4 P1 C8 N2 28.64(12) . . . . ?
O5 P1 C8 N2 -94.68(10) . . . . ?
O6 P1 C8 N2 155.78(9) . . . . ?
P1 O5 C10 C11 179.43(10) . . . . ?
P1 O6 C12 C13 -115.75(11) . . . . ?

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 O3 0.86 2.16 2.9800(15) 159.6 3_566
N2 H2 O4 0.86 2.58 2.9898(15) 110.5 .
N2 H2 O4 0.86 2.07 2.8633(15) 153.8 3_667
C2 H2B O2 0.96 2.49 3.041(2) 116.7 .
C3 H3B O2 0.96 2.46 3.0163(19) 116.8 .
C4 H4A O2 0.96 2.44 3.3504(19) 157.2 4_575
C9 H9A O3 0.93 2.25 2.8474(17) 121.3 .
C12 H12A O3 0.97 2.46 3.4329(18) 178.3 3_666

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.041

