# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1579831'
_audit_update_record             
;
2017-10-13 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        NA-15C5
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 N2 O7'
_chemical_formula_weight         440.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   14.2812(13)
_cell_length_b                   19.295(2)
_cell_length_c                   7.9526(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2191.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3080
_cell_measurement_theta_min      3.8680
_cell_measurement_theta_max      67.1710

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8513
_exptl_absorpt_correction_T_max  0.8513
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_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            6328
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         75.00
_reflns_number_total             3446
_reflns_number_gt                2886
_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)+(0.0915P)²+0.2857P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_number_reflns         3446
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1577
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_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
N1 N -0.36523(18) 0.69977(17) 0.2895(4) 0.0758(8) Uani 1 1 d . . .
N2 N -0.0424(3) 0.4204(2) 0.3730(9) 0.149(3) Uani 1 1 d . . .
O1 O 0.5780(2) 0.31308(18) 0.3308(5) 0.1126(10) Uani 1 1 d . . .
O2 O 0.37545(17) 0.29940(18) 0.1748(4) 0.1011(10) Uani 1 1 d . . .
O3 O 0.30019(14) 0.39572(12) 0.3989(4) 0.0729(6) Uani 1 1 d . . .
O4 O 0.61266(14) 0.45334(14) 0.4462(3) 0.0748(6) Uani 1 1 d . . .
O5 O 0.42147(14) 0.47986(13) 0.5169(4) 0.0741(7) Uani 1 1 d . . .
O6 O -0.43879(15) 0.66944(14) 0.3012(5) 0.0956(9) Uani 1 1 d . . .
O7 O -0.36124(18) 0.76140(16) 0.2589(6) 0.1168(12) Uani 1 1 d . . .
C1 C 0.5089(3) 0.2654(4) 0.3437(10) 0.151(3) Uani 1 1 d . . .
H1A H 0.4687 0.2783 0.4369 0.181 Uiso 1 1 calc R . .
H1B H 0.5370 0.2211 0.3712 0.181 Uiso 1 1 calc R . .
C2 C 0.4529(3) 0.2568(2) 0.2003(7) 0.1003(14) Uani 1 1 d . . .
H2A H 0.4934 0.2619 0.1031 0.120 Uiso 1 1 calc R . .
H2B H 0.4307 0.2093 0.2004 0.120 Uiso 1 1 calc R . .
C3 C 0.6225(3) 0.3290(3) 0.4836(7) 0.1015(14) Uani 1 1 d . . .
H3A H 0.6662 0.2923 0.5125 0.122 Uiso 1 1 calc R . .
H3B H 0.5763 0.3322 0.5726 0.122 Uiso 1 1 calc R . .
C4 C 0.6732(2) 0.3954(2) 0.4685(6) 0.0868(11) Uani 1 1 d . . .
H4A H 0.7105 0.4026 0.5690 0.104 Uiso 1 1 calc R . .
H4B H 0.7158 0.3928 0.3736 0.104 Uiso 1 1 calc R . .
C5 C 0.2979(2) 0.2850(2) 0.2791(6) 0.0860(11) Uani 1 1 d . . .
H5A H 0.3193 0.2674 0.3867 0.103 Uiso 1 1 calc R . .
H5B H 0.2587 0.2499 0.2272 0.103 Uiso 1 1 calc R . .
C6 C 0.17893(19) 0.48443(19) 0.3936(5) 0.0714(9) Uani 1 1 d . . .
H6A H 0.1345 0.4534 0.3533 0.086 Uiso 1 1 calc R . .
C7 C -0.0324(2) 0.4784(2) 0.3722(7) 0.0904(13) Uani 1 1 d . . .
C8 C 0.3117(2) 0.5763(2) 0.5164(5) 0.0766(10) Uani 1 1 d . . .
H8A H 0.3559 0.6074 0.5575 0.092 Uiso 1 1 calc R . .
C9 C -0.1950(2) 0.69948(19) 0.3133(6) 0.0820(11) Uani 1 1 d . . .
H9A H -0.1950 0.7475 0.3030 0.098 Uiso 1 1 calc R . .
C10 C 0.1539(2) 0.55408(18) 0.4219(5) 0.0742(10) Uani 1 1 d . . .
C11 C -0.1119(2) 0.66285(18) 0.3313(6) 0.0838(12) Uani 1 1 d . . .
H11A H -0.0555 0.6869 0.3324 0.101 Uiso 1 1 calc R . .
C12 C 0.2214(2) 0.5984(2) 0.4818(6) 0.0807(10) Uani 1 1 d . . .
H12A H 0.2060 0.6446 0.4997 0.097 Uiso 1 1 calc R . .
C13 C 0.5795(2) 0.4814(3) 0.6000(5) 0.0835(11) Uani 1 1 d . . .
H13A H 0.6284 0.5091 0.6517 0.100 Uiso 1 1 calc R . .
H13B H 0.5637 0.4441 0.6766 0.100 Uiso 1 1 calc R . .
C14 C 0.2425(2) 0.35049(18) 0.3046(5) 0.0741(9) Uani 1 1 d . . .
H14A H 0.2267 0.3712 0.1971 0.089 Uiso 1 1 calc R . .
H14B H 0.1850 0.3408 0.3651 0.089 Uiso 1 1 calc R . .
C15 C 0.4951(2) 0.5255(2) 0.5698(5) 0.0778(10) Uani 1 1 d . . .
H15A H 0.4773 0.5495 0.6721 0.093 Uiso 1 1 calc R . .
H15B H 0.5079 0.5596 0.4833 0.093 Uiso 1 1 calc R . .
C16 C 0.0609(2) 0.5816(2) 0.3941(6) 0.0759(10) Uani 1 1 d . . .
H16A H 0.0588 0.6298 0.3927 0.091 Uiso 1 1 calc R . .
C17 C 0.26859(18) 0.46209(18) 0.4251(5) 0.0645(8) Uani 1 1 d . . .
C18 C -0.2792(2) 0.59226(17) 0.3268(5) 0.0705(9) Uani 1 1 d . . .
H18A H -0.3358 0.5685 0.3247 0.085 Uiso 1 1 calc R . .
C19 C -0.0223(2) 0.55192(17) 0.3701(5) 0.0674(8) Uani 1 1 d . . .
C20 C 0.3357(2) 0.50772(19) 0.4894(5) 0.0661(8) Uani 1 1 d . . .
C21 C -0.1963(2) 0.55725(18) 0.3454(5) 0.0735(10) Uani 1 1 d . . .
H21A H -0.1973 0.5093 0.3569 0.088 Uiso 1 1 calc R . .
C22 C -0.11078(19) 0.59172(16) 0.3475(5) 0.0624(8) Uani 1 1 d . . .
C23 C -0.27710(19) 0.66253(17) 0.3115(5) 0.0653(8) Uani 1 1 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
N1 O6 1.206(4) . ?
N1 O7 1.215(4) . ?
N1 C23 1.460(4) . ?
N2 C7 1.129(5) . ?
O1 C1 1.353(6) . ?
O1 C3 1.405(7) . ?
O2 C2 1.393(4) . ?
O2 C5 1.411(5) . ?
O3 C17 1.374(4) . ?
O3 C14 1.415(4) . ?
O4 C13 1.419(5) . ?
O4 C4 1.424(5) . ?
O5 C20 1.355(4) . ?
O5 C15 1.434(4) . ?
C1 C2 1.402(8) . ?
C3 C4 1.478(6) . ?
C5 C14 1.505(5) . ?
C6 C17 1.374(4) . ?
C6 C10 1.409(5) . ?
C7 C19 1.426(5) . ?
C8 C12 1.385(5) . ?
C8 C20 1.384(5) . ?
C9 C23 1.373(4) . ?
C9 C11 1.388(4) . ?
C10 C12 1.373(5) . ?
C10 C16 1.447(4) . ?
C11 C22 1.379(5) . ?
C13 C15 1.495(5) . ?
C16 C19 1.332(4) . ?
C17 C20 1.399(5) . ?
C18 C23 1.362(5) . ?
C18 C21 1.371(4) . ?
C19 C22 1.490(4) . ?
C21 C22 1.391(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
O6 N1 O7 122.1(3) . . ?
O6 N1 C23 120.2(3) . . ?
O7 N1 C23 117.7(3) . . ?
C1 O1 C3 114.4(5) . . ?
C2 O2 C5 114.9(3) . . ?
C17 O3 C14 117.7(2) . . ?
C13 O4 C4 113.3(3) . . ?
C20 O5 C15 117.8(3) . . ?
O1 C1 C2 115.7(6) . . ?
O2 C2 C1 120.1(5) . . ?
O1 C3 C4 109.9(4) . . ?
O4 C4 C3 113.2(3) . . ?
O2 C5 C14 109.0(3) . . ?
C17 C6 C10 120.4(3) . . ?
N2 C7 C19 178.6(4) . . ?
C12 C8 C20 119.6(3) . . ?
C23 C9 C11 117.8(3) . . ?
C12 C10 C6 118.1(3) . . ?
C12 C10 C16 117.9(3) . . ?
C6 C10 C16 123.9(3) . . ?
C22 C11 C9 121.8(3) . . ?
C10 C12 C8 122.1(3) . . ?
O4 C13 C15 110.3(3) . . ?
O3 C14 C5 106.5(3) . . ?
O5 C15 C13 106.8(3) . . ?
C19 C16 C10 133.0(3) . . ?
O3 C17 C6 124.8(3) . . ?
O3 C17 C20 114.7(3) . . ?
C6 C17 C20 120.5(3) . . ?
C23 C18 C21 118.8(3) . . ?
C16 C19 C7 121.1(3) . . ?
C16 C19 C22 123.5(3) . . ?
C7 C19 C22 115.3(3) . . ?
O5 C20 C8 125.3(3) . . ?
O5 C20 C17 115.4(3) . . ?
C8 C20 C17 119.3(3) . . ?
C18 C21 C22 121.6(3) . . ?
C11 C22 C21 117.7(3) . . ?
C11 C22 C19 122.3(3) . . ?
C21 C22 C19 120.0(3) . . ?
C18 C23 C9 122.3(3) . . ?
C18 C23 N1 118.8(3) . . ?
C9 C23 N1 118.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        75.00
_diffrn_measured_fraction_theta_full 0.939
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_sad_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1579835'
_audit_update_record             
;
2017-10-13 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        NAPM-o
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H55 N2 O4 P'
_chemical_formula_weight         718.88

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   'P 21/c'

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

_cell_length_a                   14.5581(3)
_cell_length_b                   15.8079(3)
_cell_length_c                   18.6350(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.203(2)
_cell_angle_gamma                90.00
_cell_volume                     4191.63(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    13523
_cell_measurement_theta_min      4.1850
_cell_measurement_theta_max      73.7020

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ORANGE
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9787
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_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            24157
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         26.36
_reflns_number_total             8312
_reflns_number_gt                7187
_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)+(0.1000P)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         8312
_refine_ls_number_parameters     464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1290
_refine_ls_R_factor_gt           0.1215
_refine_ls_wR_factor_ref         0.3838
_refine_ls_wR_factor_gt          0.3738
_refine_ls_goodness_of_fit_ref   3.097
_refine_ls_restrained_S_all      3.097
_refine_ls_shift/su_max          0.011
_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
N1 N 0.8274(5) 0.0062(6) 1.2491(3) 0.155(3) Uani 1 1 d . . .
N2 N 1.1664(4) 0.1142(6) 1.0297(5) 0.132(3) Uani 1 1 d . . .
P1 P 0.60946(5) 0.20325(5) 1.00565(4) 0.0414(3) Uani 1 1 d . . .
C1 C 0.3825(7) 0.3394(8) 0.7634(3) 0.176(4) Uani 1 1 d . . .
H1A H 0.4023 0.3974 0.7683 0.265 Uiso 1 1 calc R . .
H1B H 0.3487 0.3293 0.7141 0.265 Uiso 1 1 calc R . .
H1C H 0.4366 0.3032 0.7742 0.265 Uiso 1 1 calc R . .
C2 C 0.2245(6) 0.3579(7) 0.8007(4) 0.167(4) Uani 1 1 d . . .
H2A H 0.2286 0.4181 0.8074 0.250 Uiso 1 1 calc R . .
H2B H 0.1895 0.3340 0.8340 0.250 Uiso 1 1 calc R . .
H2C H 0.1932 0.3454 0.7511 0.250 Uiso 1 1 calc R . .
C3 C 0.3000(7) 0.2266(6) 0.7979(5) 0.172(5) Uani 1 1 d . . .
H3A H 0.2653 0.2209 0.7482 0.257 Uiso 1 1 calc R . .
H3B H 0.2636 0.2040 0.8308 0.257 Uiso 1 1 calc R . .
H3C H 0.3582 0.1962 0.8038 0.257 Uiso 1 1 calc R . .
C4 C 0.8478(2) 0.3195(2) 1.12098(19) 0.0501(8) Uani 1 1 d . . .
C5 C 0.2648(5) 0.4018(6) 1.0841(5) 0.137(3) Uani 1 1 d . . .
H5A H 0.2245 0.4130 1.0372 0.205 Uiso 1 1 calc R . .
H5B H 0.2433 0.4332 1.1214 0.205 Uiso 1 1 calc R . .
H5C H 0.2636 0.3424 1.0946 0.205 Uiso 1 1 calc R . .
C6 C 0.4219(6) 0.4075(6) 1.1578(3) 0.135(3) Uani 1 1 d . . .
H6A H 0.4867 0.4228 1.1621 0.202 Uiso 1 1 calc R . .
H6B H 0.4174 0.3479 1.1660 0.202 Uiso 1 1 calc R . .
H6C H 0.3964 0.4381 1.1936 0.202 Uiso 1 1 calc R . .
C7 C 1.0780(4) 0.0606(5) 1.1193(4) 0.115(2) Uani 1 1 d . . .
H7A H 1.1347 0.0475 1.1507 0.138 Uiso 1 1 calc R . .
C8 C 0.8218(4) 0.0258(4) 1.1886(3) 0.1022(18) Uani 1 1 d . . .
C9 C 0.3711(6) 0.5242(4) 1.0680(5) 0.127(2) Uani 1 1 d . . .
H9A H 0.4344 0.5407 1.0676 0.190 Uiso 1 1 calc R . .
H9B H 0.3497 0.5544 1.1061 0.190 Uiso 1 1 calc R . .
H9C H 0.3311 0.5372 1.0214 0.190 Uiso 1 1 calc R . .
C10 C 1.0257(4) 0.3231(4) 1.1276(4) 0.1060(19) Uani 1 1 d . . .
H10A H 1.0751 0.3554 1.1139 0.159 Uiso 1 1 calc R . .
H10B H 1.0236 0.2678 1.1061 0.159 Uiso 1 1 calc R . .
H10C H 1.0375 0.3180 1.1801 0.159 Uiso 1 1 calc R . .
C12 C 0.9943(4) 0.0444(4) 1.1396(3) 0.0941(17) Uani 1 1 d . . .
H12A H 0.9945 0.0202 1.1851 0.113 Uiso 1 1 calc R . .
C13 C 1.0766(3) 0.0964(4) 1.0521(4) 0.0935(17) Uani 1 1 d . . .
C14 C 0.9962(4) 0.1176(4) 1.0055(3) 0.0903(15) Uani 1 1 d . . .
H14A H 0.9974 0.1418 0.9602 0.108 Uiso 1 1 calc R . .
C15 C 0.9186(4) 0.3753(5) 1.0173(3) 0.1031(19) Uani 1 1 d . . .
H15A H 0.9710 0.4054 1.0059 0.155 Uiso 1 1 calc R . .
H15B H 0.8615 0.4053 0.9977 0.155 Uiso 1 1 calc R . .
H15C H 0.9155 0.3197 0.9962 0.155 Uiso 1 1 calc R . .
C16 C 0.9375(4) 0.4568(3) 1.1336(4) 0.0986(17) Uani 1 1 d . . .
H16A H 0.9894 0.4865 1.1212 0.148 Uiso 1 1 calc R . .
H16B H 0.9466 0.4524 1.1860 0.148 Uiso 1 1 calc R . .
H16C H 0.8803 0.4870 1.1147 0.148 Uiso 1 1 calc R . .
C17 C 0.9108(3) 0.1028(4) 1.0260(3) 0.0849(14) Uani 1 1 d . . .
H17A H 0.8550 0.1191 0.9948 0.102 Uiso 1 1 calc R . .
C18 C 0.5261(4) -0.0251(3) 1.1321(3) 0.0864(14) Uani 1 1 d . . .
H18A H 0.5105 -0.0719 1.1574 0.104 Uiso 1 1 calc R . .
C19 C 0.3340(6) 0.5191(5) 0.8925(6) 0.154(4) Uani 1 1 d . . .
H19A H 0.2879 0.5628 0.8784 0.231 Uiso 1 1 calc R . .
H19B H 0.3551 0.4994 0.8500 0.231 Uiso 1 1 calc R . .
H19C H 0.3864 0.5412 0.9277 0.231 Uiso 1 1 calc R . .
C20 C 0.6149(4) -0.0156(3) 1.1219(3) 0.0765(12) Uani 1 1 d . . .
H20A H 0.6602 -0.0555 1.1417 0.092 Uiso 1 1 calc R . .
C21 C 0.3679(3) 0.4291(3) 1.0823(2) 0.0714(11) Uani 1 1 d . . .
C22 C 0.4583(3) 0.0350(3) 1.1047(2) 0.0732(11) Uani 1 1 d . . .
H22A H 0.3974 0.0284 1.1119 0.088 Uiso 1 1 calc R . .
C23 C 0.7703(12) 0.3541(11) 1.3317(7) 0.320(13) Uani 1 1 d . . .
H23A H 0.7530 0.3527 1.3786 0.481 Uiso 1 1 calc R . .
H23B H 0.7474 0.4054 1.3065 0.481 Uiso 1 1 calc R . .
H23C H 0.8375 0.3521 1.3386 0.481 Uiso 1 1 calc R . .
C24 C 0.9080(3) 0.0643(3) 1.0921(2) 0.0705(11) Uani 1 1 d . . .
C25 C 0.8180(3) 0.0500(3) 1.1138(2) 0.0685(11) Uani 1 1 d . . .
C26 C 0.4780(2) 0.3235(2) 1.04072(17) 0.0493(7) Uani 1 1 d . . .
H26A H 0.5119 0.3218 1.0889 0.059 Uiso 1 1 calc R . .
C27 C 0.6398(3) 0.0515(2) 1.08295(18) 0.0562(9) Uani 1 1 d . . .
C28 C 0.7306(3) 0.2835(3) 1.28926(18) 0.0629(10) Uani 1 1 d . . .
C29 C 0.3539(3) 0.3776(3) 0.9497(2) 0.0691(11) Uani 1 1 d . . .
C30 C 0.9311(3) 0.3680(3) 1.1001(2) 0.0685(10) Uani 1 1 d . . .
C31 C 0.3205(3) 0.3212(3) 0.8154(2) 0.0684(11) Uani 1 1 d . . .
C32 C 0.3755(2) 0.3256(2) 0.89595(17) 0.0514(8) Uani 1 1 d . . .
C33 C 0.8382(2) 0.3077(2) 1.19384(19) 0.0534(8) Uani 1 1 d . . .
C34 C 0.7547(2) 0.2790(2) 1.21162(17) 0.0510(8) Uani 1 1 d . . .
C35 C 0.7337(3) 0.0602(3) 1.0680(2) 0.0608(9) Uani 1 1 d . . .
H35A H 0.7358 0.0748 1.0200 0.073 Uiso 1 1 calc R . .
C36 C 0.4005(2) 0.3758(2) 1.02383(19) 0.0512(8) Uani 1 1 d . . .
C37 C 0.4807(3) 0.1042(2) 1.06715(19) 0.0564(8) Uani 1 1 d . . .
H37A H 0.4351 0.1447 1.0496 0.068 Uiso 1 1 calc R . .
C38 C 0.4560(2) 0.2751(2) 0.91703(16) 0.0476(7) Uani 1 1 d . . .
H38A H 0.4754 0.2418 0.8819 0.057 Uiso 1 1 calc R . .
C39 C 0.5711(2) 0.1139(2) 1.05525(16) 0.0468(7) Uani 1 1 d . . .
C40 C 0.9697(4) 0.2561(6) 1.2789(4) 0.136(3) Uani 1 1 d . . .
H40A H 1.0202 0.2739 1.3179 0.204 Uiso 1 1 calc R . .
H40B H 0.9950 0.2308 1.2405 0.204 Uiso 1 1 calc R . .
H40C H 0.9314 0.2155 1.2975 0.204 Uiso 1 1 calc R . .
C41 C 0.6948(2) 0.2519(2) 1.08119(15) 0.0422(7) Uani 1 1 d . . .
C42 C 0.7741(2) 0.2892(2) 1.06552(17) 0.0453(7) Uani 1 1 d . . .
H42A H 0.7790 0.2944 1.0168 0.054 Uiso 1 1 calc R . .
C43 C 0.6848(2) 0.2490(2) 1.15396(16) 0.0468(7) Uani 1 1 d . . .
H43A H 0.6301 0.2264 1.1644 0.056 Uiso 1 1 calc R . .
C44 C 0.5073(2) 0.2734(2) 0.98857(16) 0.0435(7) Uani 1 1 d . . .
C45 C 0.6310(5) 0.2932(11) 1.2829(3) 0.295(11) Uani 1 1 d . . .
H45A H 0.6172 0.2958 1.3310 0.442 Uiso 1 1 calc R . .
H45B H 0.5988 0.2459 1.2567 0.442 Uiso 1 1 calc R . .
H45C H 0.6104 0.3445 1.2568 0.442 Uiso 1 1 calc R . .
C46 C 0.7324(10) 0.1960(8) 1.3192(8) 0.210(5) Uiso 1 1 d . . .
H46A H 0.7175 0.1976 1.3669 0.314 Uiso 1 1 calc R . .
H46B H 0.7939 0.1723 1.3229 0.314 Uiso 1 1 calc R . .
H46C H 0.6870 0.1618 1.2870 0.314 Uiso 1 1 calc R . .
O1 O 1.2369(4) 0.0942(8) 1.0723(5) 0.258(6) Uani 1 1 d . . .
O2 O 1.1653(5) 0.1411(5) 0.9709(5) 0.166(3) Uani 1 1 d . . .
O3 O 0.2858(4) 0.4383(4) 0.9302(2) 0.180(3) Uani 1 1 d . . .
O4 O 0.9131(2) 0.3284(2) 1.25033(15) 0.0825(10) Uani 1 1 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
N1 C8 1.155(8) . ?
N2 O2 1.171(9) . ?
N2 O1 1.201(9) . ?
N2 C13 1.481(9) . ?
P1 C44 1.828(3) . ?
P1 C41 1.837(3) . ?
P1 C39 1.838(4) . ?
C1 C31 1.485(10) . ?
C2 C31 1.485(8) . ?
C3 C31 1.546(9) . ?
C4 C33 1.407(5) . ?
C4 C42 1.407(4) . ?
C4 C30 1.552(5) . ?
C5 C21 1.568(8) . ?
C6 C21 1.498(7) . ?
C7 C13 1.370(10) . ?
C7 C12 1.374(9) . ?
C8 C25 1.435(7) . ?
C9 C21 1.528(8) . ?
C10 C30 1.538(7) . ?
C12 C24 1.411(5) . ?
C13 C14 1.346(7) . ?
C14 C17 1.395(8) . ?
C15 C30 1.518(7) . ?
C16 C30 1.531(7) . ?
C17 C24 1.382(7) . ?
C18 C20 1.354(7) . ?
C18 C22 1.386(7) . ?
C19 O3 1.680(11) . ?
C20 C27 1.377(6) . ?
C21 C36 1.531(5) . ?
C22 C37 1.375(6) . ?
C23 C28 1.419(9) . ?
C24 C25 1.468(7) . ?
C25 C35 1.348(5) . ?
C26 C36 1.380(5) . ?
C26 C44 1.389(5) . ?
C27 C39 1.422(5) . ?
C27 C35 1.458(6) . ?
C28 C45 1.438(9) . ?
C28 C46 1.489(14) . ?
C28 C34 1.561(5) . ?
C29 O3 1.373(5) . ?
C29 C32 1.382(5) . ?
C29 C36 1.404(5) . ?
C31 C32 1.547(4) . ?
C32 C38 1.403(4) . ?
C33 O4 1.386(4) . ?
C33 C34 1.401(5) . ?
C34 C43 1.397(4) . ?
C37 C39 1.389(5) . ?
C38 C44 1.384(4) . ?
C40 O4 1.443(8) . ?
C41 C42 1.382(4) . ?
C41 C43 1.395(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
O2 N2 O1 123.7(9) . . ?
O2 N2 C13 119.7(6) . . ?
O1 N2 C13 116.4(9) . . ?
C44 P1 C41 105.85(14) . . ?
C44 P1 C39 103.36(15) . . ?
C41 P1 C39 99.44(13) . . ?
C33 C4 C42 116.6(3) . . ?
C33 C4 C30 123.4(3) . . ?
C42 C4 C30 119.9(3) . . ?
C13 C7 C12 119.1(4) . . ?
N1 C8 C25 178.2(7) . . ?
C7 C12 C24 120.6(6) . . ?
C14 C13 C7 122.4(6) . . ?
C14 C13 N2 118.0(7) . . ?
C7 C13 N2 119.6(6) . . ?
C13 C14 C17 119.0(6) . . ?
C24 C17 C14 121.0(4) . . ?
C20 C18 C22 119.9(4) . . ?
C18 C20 C27 121.7(4) . . ?
C6 C21 C9 111.0(6) . . ?
C6 C21 C36 111.2(4) . . ?
C9 C21 C36 113.1(4) . . ?
C6 C21 C5 103.5(6) . . ?
C9 C21 C5 109.8(5) . . ?
C36 C21 C5 107.7(4) . . ?
C18 C22 C37 120.4(5) . . ?
C17 C24 C12 117.8(5) . . ?
C17 C24 C25 120.7(3) . . ?
C12 C24 C25 121.4(5) . . ?
C35 C25 C8 119.4(5) . . ?
C35 C25 C24 123.5(4) . . ?
C8 C25 C24 117.1(4) . . ?
C36 C26 C44 122.6(3) . . ?
C20 C27 C39 118.8(4) . . ?
C20 C27 C35 122.4(4) . . ?
C39 C27 C35 118.8(3) . . ?
C23 C28 C45 104.3(9) . . ?
C23 C28 C46 123.3(10) . . ?
C45 C28 C46 93.9(9) . . ?
C23 C28 C34 114.0(5) . . ?
C45 C28 C34 110.4(4) . . ?
C46 C28 C34 108.4(6) . . ?
O3 C29 C32 119.0(3) . . ?
O3 C29 C36 116.5(4) . . ?
C32 C29 C36 124.4(3) . . ?
C15 C30 C16 109.2(5) . . ?
C15 C30 C10 106.3(5) . . ?
C16 C30 C10 108.3(4) . . ?
C15 C30 C4 111.1(3) . . ?
C16 C30 C4 109.5(4) . . ?
C10 C30 C4 112.3(4) . . ?
C2 C31 C1 118.8(6) . . ?
C2 C31 C32 115.9(4) . . ?
C1 C31 C32 111.3(4) . . ?
C2 C31 C3 101.9(7) . . ?
C1 C31 C3 99.6(7) . . ?
C32 C31 C3 106.6(4) . . ?
C29 C32 C38 116.1(3) . . ?
C29 C32 C31 125.4(3) . . ?
C38 C32 C31 118.5(3) . . ?
O4 C33 C34 118.7(3) . . ?
O4 C33 C4 118.6(3) . . ?
C34 C33 C4 122.7(3) . . ?
C43 C34 C33 117.1(3) . . ?
C43 C34 C28 117.3(3) . . ?
C33 C34 C28 125.5(3) . . ?
C25 C35 C27 129.2(4) . . ?
C26 C36 C29 116.0(3) . . ?
C26 C36 C21 121.9(3) . . ?
C29 C36 C21 122.1(3) . . ?
C22 C37 C39 120.3(4) . . ?
C44 C38 C32 122.0(3) . . ?
C37 C39 C27 118.9(3) . . ?
C37 C39 P1 124.3(3) . . ?
C27 C39 P1 116.8(3) . . ?
C42 C41 C43 118.9(3) . . ?
C42 C41 P1 118.5(2) . . ?
C43 C41 P1 122.6(2) . . ?
C41 C42 C4 122.1(3) . . ?
C41 C43 C34 121.9(3) . . ?
C38 C44 C26 118.6(3) . . ?
C38 C44 P1 115.7(2) . . ?
C26 C44 P1 125.7(2) . . ?
C29 O3 C19 107.5(6) . . ?
C33 O4 C40 112.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         1.637
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.091
####################################################################### 
# 
# 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_exp_544
_database_code_depnum_ccdc_archive 'CCDC 1579834'
_audit_update_record             
;
2017-10-13 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        NAIF
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 F N3 O2'
_chemical_formula_weight         451.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.8722(3)
_cell_length_b                   12.1460(5)
_cell_length_c                   15.6701(5)
_cell_angle_alpha                109.070(3)
_cell_angle_beta                 91.048(3)
_cell_angle_gamma                106.353(3)
_cell_volume                     1177.38(8)
_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       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.706
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11748
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.043
_diffrn_reflns_theta_max         74.288
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4635
_reflns_number_gt                3612
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0749P)²+0.1503P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4635
_refine_ls_number_parameters     320
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1627
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_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
C1 C 0.9501(2) 0.83628(14) 0.13248(11) 0.0480(4) Uani 1 1 d . . . . .
C2 C 1.1190(3) 0.89319(15) 0.09619(12) 0.0573(4) Uani 1 1 d . . . . .
H2 H 1.1508 0.9755 0.1029 0.069 Uiso 1 1 calc R U . . .
C3 C 1.2354(3) 0.82282(17) 0.05039(13) 0.0606(4) Uani 1 1 d . . . . .
H3 H 1.3461 0.8582 0.0247 0.073 Uiso 1 1 calc R U . . .
C4 C 1.1927(3) 0.70025(17) 0.04126(12) 0.0583(4) Uani 1 1 d . . . . .
H4 H 1.2747 0.6555 0.0096 0.070 Uiso 1 1 calc R U . . .
C5 C 1.0315(2) 0.64465(15) 0.07827(11) 0.0525(4) Uani 1 1 d . . . . .
H5 H 1.0052 0.5632 0.0731 0.063 Uiso 1 1 calc R U . . .
C6 C 0.9068(2) 0.71275(13) 0.12409(10) 0.0458(3) Uani 1 1 d . . . . .
C7 C 0.7256(2) 0.68053(13) 0.16498(10) 0.0455(3) Uani 1 1 d . . . . .
C8 C 0.6227(2) 0.55547(13) 0.16347(10) 0.0471(4) Uani 1 1 d . . . . .
C9 C 0.7219(3) 0.49745(16) 0.20380(13) 0.0651(5) Uani 1 1 d . . . . .
H9 H 0.8530 0.5395 0.2341 0.078 Uiso 1 1 calc R U . . .
C10 C 0.6322(4) 0.37870(18) 0.20052(16) 0.0787(6) Uani 1 1 d . . . . .
H10 H 0.6996 0.3416 0.2294 0.094 Uiso 1 1 calc R U . . .
C11 C 0.4422(3) 0.31759(17) 0.15382(16) 0.0729(5) Uani 1 1 d . . . . .
C12 C 0.3390(3) 0.36931(18) 0.11204(16) 0.0754(6) Uani 1 1 d . . . . .
H12 H 0.2094 0.3254 0.0806 0.090 Uiso 1 1 calc R U . . .
C13 C 0.4294(3) 0.48853(16) 0.11683(14) 0.0629(5) Uani 1 1 d . . . . .
H13 H 0.3594 0.5247 0.0882 0.076 Uiso 1 1 calc R U . . .
C14 C 0.6649(2) 0.78487(14) 0.19748(10) 0.0474(4) Uani 1 1 d . . . . .
C15 C 0.8047(3) 1.00874(14) 0.20883(13) 0.0592(4) Uani 1 1 d . . . . .
H15 H 0.6813 1.0123 0.2386 0.071 Uiso 1 1 calc R U . . .
C16 C 0.7927(4) 1.0549(2) 0.12997(17) 0.0822(6) Uani 1 1 d . . . . .
H16A H 0.9191 1.0630 0.1039 0.123 Uiso 1 1 calc R U . . .
H16B H 0.7687 1.1330 0.1518 0.123 Uiso 1 1 calc R U . . .
H16C H 0.6828 0.9977 0.0845 0.123 Uiso 1 1 calc R U . . .
C17 C 0.9850(4) 1.08812(18) 0.28009(15) 0.0813(6) Uani 1 1 d . . . . .
H17A H 0.9796 1.0584 0.3300 0.122 Uiso 1 1 calc R U . . .
H17B H 0.9803 1.1709 0.3016 0.122 Uiso 1 1 calc R U . . .
H17C H 1.1096 1.0855 0.2539 0.122 Uiso 1 1 calc R U . . .
C18 C 0.4936(2) 0.80361(14) 0.24522(11) 0.0520(4) Uani 1 1 d . . . . .
H18 H 0.4518 0.8697 0.2442 0.062 Uiso 1 1 calc R U . . .
C19 C 0.3882(2) 0.73532(16) 0.29095(11) 0.0526(4) Uani 1 1 d . . . . .
H19 H 0.4245 0.6678 0.2927 0.063 Uiso 1 1 calc R U . . .
C20 C 0.2220(2) 0.76350(15) 0.33707(11) 0.0537(4) Uani 1 1 d . . . . .
H20 H 0.1900 0.8318 0.3342 0.064 Uiso 1 1 calc R U . . .
C21 C 0.1061(2) 0.69977(15) 0.38477(11) 0.0519(4) Uani 1 1 d . . . . .
C22 C 0.1498(3) 0.5920(2) 0.38605(15) 0.0697(5) Uani 1 1 d . . . . .
C23 C -0.0625(2) 0.73144(15) 0.43395(11) 0.0524(4) Uani 1 1 d . . . . .
C24 C -0.1668(3) 0.66103(18) 0.48277(14) 0.0675(5) Uani 1 1 d . . . . .
H24 H -0.1309 0.5929 0.4832 0.081 Uiso 1 1 calc R U . . .
C25 C -0.3223(3) 0.6904(2) 0.53049(15) 0.0728(5) Uani 1 1 d . . . . .
H25 H -0.3916 0.6423 0.5626 0.087 Uiso 1 1 calc R U . . .
C26 C -0.3732(3) 0.79128(17) 0.52991(12) 0.0607(4) Uani 1 1 d . . . . .
C27 C -0.2763(3) 0.86267(18) 0.48187(13) 0.0624(4) Uani 1 1 d . . . . .
H27 H -0.3140 0.9303 0.4816 0.075 Uiso 1 1 calc R U . . .
C28 C -0.1221(3) 0.83186(17) 0.43412(13) 0.0609(4) Uani 1 1 d . . . . .
H28 H -0.0559 0.8794 0.4011 0.073 Uiso 1 1 calc R U . . .
F1 F 0.3559(2) 0.20001(11) 0.14813(13) 0.1162(6) Uani 1 1 d . . . . .
N1 N 0.8017(2) 0.88011(11) 0.17696(9) 0.0504(3) Uani 1 1 d . . . . .
N2 N 0.216(4) 0.526(3) 0.402(3) 0.088(4) Uani 0.37(6) 1 d . U P A 1
N2' N 0.163(4) 0.4937(19) 0.3751(16) 0.095(3) Uani 0.63(6) 1 d . U P A 2
N3 N -0.5326(3) 0.82640(19) 0.58375(13) 0.0795(5) Uani 1 1 d . . . . .
O1 O -0.6262(4) 0.7594(2) 0.62161(18) 0.1392(9) Uani 1 1 d . . . . .
O2 O -0.5682(3) 0.91974(18) 0.58679(14) 0.1066(6) Uani 1 1 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
C1 N1 1.378(2) . ?
C1 C6 1.406(2) . ?
C1 C2 1.406(2) . ?
C2 C3 1.375(2) . ?
C3 C4 1.391(3) . ?
C4 C5 1.370(2) . ?
C5 C6 1.402(2) . ?
C6 C7 1.426(2) . ?
C7 C14 1.387(2) . ?
C7 C8 1.4760(19) . ?
C8 C9 1.381(2) . ?
C8 C13 1.388(2) . ?
C9 C10 1.383(2) . ?
C10 C11 1.362(3) . ?
C11 C12 1.353(3) . ?
C11 F1 1.356(2) . ?
C12 C13 1.382(2) . ?
C14 N1 1.4025(18) . ?
C14 C18 1.439(2) . ?
C15 N1 1.471(2) . ?
C15 C17 1.511(3) . ?
C15 C16 1.524(3) . ?
C18 C19 1.340(2) . ?
C19 C20 1.426(2) . ?
C20 C21 1.358(2) . ?
C21 C22 1.429(3) . ?
C21 C23 1.474(2) . ?
C22 N2 1.12(2) . ?
C22 N2' 1.180(15) . ?
C23 C24 1.390(2) . ?
C23 C28 1.391(2) . ?
C24 C25 1.377(3) . ?
C25 C26 1.369(3) . ?
C26 C27 1.372(3) . ?
C26 N3 1.468(2) . ?
C27 C28 1.376(3) . ?
N3 O1 1.209(3) . ?
N3 O2 1.212(2) . ?

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
N1 C1 C6 108.28(13) . . ?
N1 C1 C2 131.01(14) . . ?
C6 C1 C2 120.69(15) . . ?
C3 C2 C1 117.61(15) . . ?
C2 C3 C4 122.02(15) . . ?
C5 C4 C3 120.85(16) . . ?
C4 C5 C6 118.86(15) . . ?
C5 C6 C1 119.95(14) . . ?
C5 C6 C7 132.23(14) . . ?
C1 C6 C7 107.78(14) . . ?
C14 C7 C6 106.58(13) . . ?
C14 C7 C8 129.42(14) . . ?
C6 C7 C8 123.82(14) . . ?
C9 C8 C13 117.25(14) . . ?
C9 C8 C7 120.74(14) . . ?
C13 C8 C7 121.88(14) . . ?
C8 C9 C10 121.99(17) . . ?
C11 C10 C9 118.11(18) . . ?
C12 C11 F1 119.16(19) . . ?
C12 C11 C10 122.43(17) . . ?
F1 C11 C10 118.40(19) . . ?
C11 C12 C13 118.84(18) . . ?
C12 C13 C8 121.36(17) . . ?
C7 C14 N1 109.23(13) . . ?
C7 C14 C18 129.76(14) . . ?
N1 C14 C18 121.01(14) . . ?
N1 C15 C17 111.10(16) . . ?
N1 C15 C16 111.75(16) . . ?
C17 C15 C16 113.01(16) . . ?
C19 C18 C14 126.49(16) . . ?
C18 C19 C20 121.72(16) . . ?
C21 C20 C19 126.00(17) . . ?
C20 C21 C22 117.02(16) . . ?
C20 C21 C23 125.50(16) . . ?
C22 C21 C23 117.48(14) . . ?
N2 C22 C21 164(2) . . ?
N2' C22 C21 169.4(15) . . ?
C24 C23 C28 117.69(16) . . ?
C24 C23 C21 120.32(16) . . ?
C28 C23 C21 121.98(15) . . ?
C25 C24 C23 121.20(18) . . ?
C26 C25 C24 119.02(18) . . ?
C25 C26 C27 121.85(17) . . ?
C25 C26 N3 119.43(17) . . ?
C27 C26 N3 118.70(18) . . ?
C26 C27 C28 118.49(18) . . ?
C27 C28 C23 121.74(17) . . ?
C1 N1 C14 108.13(12) . . ?
C1 N1 C15 125.29(13) . . ?
C14 N1 C15 126.02(14) . . ?
O1 N3 O2 122.7(2) . . ?
O1 N3 C26 118.5(2) . . ?
O2 N3 C26 118.75(19) . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.038



####################################################################### 
# 
# 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_sad_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1579836'
_audit_update_record             
;
2017-10-13 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        NAPM-y
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H55 N2 O4 P'
_chemical_formula_weight         718.88

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                   9.3357(5)
_cell_length_b                   14.2823(8)
_cell_length_c                   16.5623(8)
_cell_angle_alpha                75.638(5)
_cell_angle_beta                 89.724(4)
_cell_angle_gamma                76.795(5)
_cell_volume                     2079.61(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    10695
_cell_measurement_theta_min      4.8580
_cell_measurement_theta_max      73.8560

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_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            20825
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         26.34
_reflns_number_total             8188
_reflns_number_gt                7031
_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)+(0.0970P)²+1.6402P] 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         8188
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.2156
_refine_ls_wR_factor_gt          0.2103
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.003
_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
N1 N 0.5016(4) 0.2646(3) 0.4139(2) 0.0837(9) Uani 1 1 d . . .
N2 N 1.0041(7) 0.5834(3) 0.3786(3) 0.1139(15) Uani 1 1 d . . .
P1 P 1.00116(7) 0.04788(4) 0.30173(4) 0.03477(18) Uani 1 1 d . . .
O1 O 0.9238(6) 0.6576(3) 0.3858(4) 0.163(2) Uani 1 1 d . . .
O2 O 1.2574(3) -0.26438(17) 0.12608(14) 0.0656(6) Uani 1 1 d . . .
O3 O 0.5025(2) 0.37866(14) 0.12829(13) 0.0516(5) Uani 1 1 d . . .
O4 O 1.1315(7) 0.5778(4) 0.3618(5) 0.195(3) Uani 1 1 d . . .
C1 C 1.5440(5) -0.2105(5) 0.2578(4) 0.129(2) Uani 1 1 d . . .
H1A H 1.6332 -0.2548 0.2852 0.193 Uiso 1 1 calc R . .
H1B H 1.5291 -0.1489 0.2737 0.193 Uiso 1 1 calc R . .
H1C H 1.5514 -0.1981 0.1984 0.193 Uiso 1 1 calc R . .
C2 C 0.3731(5) 0.1549(5) 0.2571(3) 0.117(2) Uani 1 1 d . . .
H2A H 0.3524 0.2149 0.2758 0.176 Uiso 1 1 calc R . .
H2B H 0.4379 0.1029 0.2977 0.176 Uiso 1 1 calc R . .
H2C H 0.2827 0.1357 0.2501 0.176 Uiso 1 1 calc R . .
C3 C 1.4468(6) -0.3609(3) 0.2685(3) 0.1090(17) Uani 1 1 d . . .
H3A H 1.5393 -0.3994 0.2964 0.163 Uiso 1 1 calc R . .
H3B H 1.4509 -0.3563 0.2098 0.163 Uiso 1 1 calc R . .
H3C H 1.3695 -0.3925 0.2904 0.163 Uiso 1 1 calc R . .
C4 C 1.4054(6) -0.2744(4) 0.3770(3) 0.1036(17) Uani 1 1 d . . .
H4A H 1.4959 -0.3169 0.4046 0.155 Uiso 1 1 calc R . .
H4B H 1.3255 -0.3055 0.3942 0.155 Uiso 1 1 calc R . .
H4C H 1.3881 -0.2120 0.3916 0.155 Uiso 1 1 calc R . .
C5 C 1.0425(5) 0.4067(3) 0.3793(3) 0.0884(12) Uani 1 1 d . . .
H5A H 1.1387 0.4060 0.3642 0.106 Uiso 1 1 calc R . .
C6 C 0.4788(5) 0.0749(3) 0.1456(3) 0.0943(14) Uani 1 1 d . . .
H6A H 0.3884 0.0559 0.1384 0.142 Uiso 1 1 calc R . .
H6B H 0.5430 0.0231 0.1868 0.142 Uiso 1 1 calc R . .
H6C H 0.5258 0.0855 0.0935 0.142 Uiso 1 1 calc R . .
C7 C 1.3597(5) -0.2295(4) 0.0680(3) 0.0927(13) Uani 1 1 d . . .
H7A H 1.4000 -0.2793 0.0391 0.139 Uiso 1 1 calc R . .
H7B H 1.4379 -0.2162 0.0976 0.139 Uiso 1 1 calc R . .
H7C H 1.3097 -0.1696 0.0284 0.139 Uiso 1 1 calc R . .
C8 C 0.3379(4) 0.2449(3) 0.1056(3) 0.0845(12) Uani 1 1 d . . .
H8A H 0.3100 0.3087 0.1179 0.127 Uiso 1 1 calc R . .
H8B H 0.2518 0.2199 0.1019 0.127 Uiso 1 1 calc R . .
H8C H 0.3847 0.2516 0.0534 0.127 Uiso 1 1 calc R . .
C9 C 0.9500(6) 0.4921(3) 0.3913(3) 0.0806(11) Uani 1 1 d . . .
C10 C 0.7561(4) 0.4105(2) 0.4247(2) 0.0696(9) Uani 1 1 d . . .
H10A H 0.6598 0.4120 0.4402 0.084 Uiso 1 1 calc R . .
C11 C 0.8097(5) 0.4949(2) 0.4139(3) 0.0827(12) Uani 1 1 d . . .
H11A H 0.7501 0.5533 0.4221 0.099 Uiso 1 1 calc R . .
C12 C 0.7925(4) -0.1046(4) 0.0733(3) 0.0841(12) Uani 1 1 d . . .
H12A H 0.7356 -0.1221 0.0336 0.126 Uiso 1 1 calc R . .
H12B H 0.7949 -0.0358 0.0540 0.126 Uiso 1 1 calc R . .
H12C H 0.7483 -0.1154 0.1263 0.126 Uiso 1 1 calc R . .
C13 C 0.7247(5) 0.4954(3) 0.1600(3) 0.0915(14) Uani 1 1 d . . .
H13A H 0.7590 0.4753 0.2176 0.137 Uiso 1 1 calc R . .
H13B H 0.6195 0.5050 0.1562 0.137 Uiso 1 1 calc R . .
H13C H 0.7508 0.5566 0.1334 0.137 Uiso 1 1 calc R . .
C14 C 0.9403(5) -0.2778(3) 0.1157(3) 0.0866(12) Uani 1 1 d . . .
H14A H 0.8810 -0.2949 0.0769 0.130 Uiso 1 1 calc R . .
H14B H 0.8965 -0.2862 0.1688 0.130 Uiso 1 1 calc R . .
H14C H 1.0375 -0.3204 0.1220 0.130 Uiso 1 1 calc R . .
C15 C 0.7417(5) 0.4464(3) 0.0240(2) 0.0790(11) Uani 1 1 d . . .
H15A H 0.6374 0.4519 0.0198 0.118 Uiso 1 1 calc R . .
H15B H 0.7915 0.3973 -0.0035 0.118 Uiso 1 1 calc R . .
H15C H 0.7626 0.5094 -0.0021 0.118 Uiso 1 1 calc R . .
C16 C 0.9885(4) 0.3226(3) 0.3903(3) 0.0737(10) Uani 1 1 d . . .
H16A H 1.0492 0.2645 0.3824 0.088 Uiso 1 1 calc R . .
C17 C 0.6974(4) -0.0754(2) 0.5016(2) 0.0614(8) Uani 1 1 d . . .
H17A H 0.6326 -0.0973 0.5407 0.074 Uiso 1 1 calc R . .
C18 C 0.9613(4) 0.4088(2) 0.1172(3) 0.0741(10) Uani 1 1 d . . .
H18A H 1.0012 0.3891 0.1738 0.111 Uiso 1 1 calc R . .
H18B H 0.9784 0.4726 0.0901 0.111 Uiso 1 1 calc R . .
H18C H 1.0082 0.3606 0.0881 0.111 Uiso 1 1 calc R . .
C19 C 1.0106(5) -0.1536(3) -0.0044(2) 0.0770(10) Uani 1 1 d . . .
H19A H 0.9474 -0.1705 -0.0414 0.116 Uiso 1 1 calc R . .
H19B H 1.1079 -0.1954 -0.0015 0.116 Uiso 1 1 calc R . .
H19C H 1.0145 -0.0853 -0.0251 0.116 Uiso 1 1 calc R . .
C20 C 0.4199(4) 0.4141(3) 0.1920(3) 0.0739(10) Uani 1 1 d . . .
H20A H 0.3419 0.4704 0.1667 0.111 Uiso 1 1 calc R . .
H20B H 0.4836 0.4333 0.2269 0.111 Uiso 1 1 calc R . .
H20C H 0.3787 0.3623 0.2250 0.111 Uiso 1 1 calc R . .
C21 C 0.8448(4) 0.3232(2) 0.41277(18) 0.0534(7) Uani 1 1 d . . .
C22 C 0.7596(4) -0.1332(2) 0.44973(19) 0.0579(7) Uani 1 1 d . . .
H22A H 0.7375 -0.1945 0.4543 0.069 Uiso 1 1 calc R . .
C23 C 1.4161(4) -0.2568(2) 0.2828(2) 0.0598(8) Uani 1 1 d . . .
C25 C 0.8551(3) -0.10070(19) 0.39054(17) 0.0481(6) Uani 1 1 d . . .
H25A H 0.8967 -0.1406 0.3559 0.058 Uiso 1 1 calc R . .
C26 C 0.7310(4) 0.0149(2) 0.49576(18) 0.0553(7) Uani 1 1 d . . .
H26A H 0.6885 0.0538 0.5310 0.066 Uiso 1 1 calc R . .
C27 C 0.9498(4) -0.1692(2) 0.08288(19) 0.0577(7) Uani 1 1 d . . .
C28 C 0.6281(4) 0.2486(2) 0.4175(2) 0.0590(7) Uani 1 1 d . . .
C29 C 0.8277(3) 0.04862(18) 0.43775(16) 0.0434(6) Uani 1 1 d . . .
C30 C 0.4452(3) 0.1725(2) 0.1751(2) 0.0543(7) Uani 1 1 d . . .
C31 C 0.7865(3) 0.2331(2) 0.42288(17) 0.0491(6) Uani 1 1 d . . .
C32 C 0.7957(3) 0.41508(18) 0.11673(18) 0.0487(6) Uani 1 1 d . . .
C33 C 0.9860(3) -0.06853(19) 0.18522(16) 0.0437(6) Uani 1 1 d . . .
H33A H 0.8905 -0.0309 0.1696 0.052 Uiso 1 1 calc R . .
C34 C 0.8722(3) 0.14174(19) 0.43232(16) 0.0462(6) Uani 1 1 d . . .
H34A H 0.9732 0.1368 0.4359 0.055 Uiso 1 1 calc R . .
C35 C 1.2694(3) -0.1877(2) 0.23969(17) 0.0482(6) Uani 1 1 d . . .
C36 C 1.1919(3) -0.1972(2) 0.17098(17) 0.0491(6) Uani 1 1 d . . .
C37 C 1.0656(3) -0.04879(17) 0.24693(15) 0.0397(5) Uani 1 1 d . . .
C38 C 0.7111(3) 0.12585(18) 0.22628(16) 0.0408(5) Uani 1 1 d . . .
H38A H 0.6956 0.0626 0.2482 0.049 Uiso 1 1 calc R . .
C39 C 1.0458(3) -0.1434(2) 0.14614(16) 0.0463(6) Uani 1 1 d . . .
C40 C 0.6190(3) 0.29713(18) 0.15828(15) 0.0398(5) Uani 1 1 d . . .
C41 C 0.8505(3) 0.14081(16) 0.23536(15) 0.0360(5) Uani 1 1 d . . .
C42 C 1.2039(3) -0.10889(19) 0.27362(17) 0.0450(6) Uani 1 1 d . . .
H42A H 1.2557 -0.0963 0.3160 0.054 Uiso 1 1 calc R . .
C43 C 0.5925(3) 0.20139(19) 0.18566(16) 0.0412(5) Uani 1 1 d . . .
C44 C 0.8894(3) -0.00906(17) 0.38252(15) 0.0376(5) Uani 1 1 d . . .
C45 C 0.8754(3) 0.23404(17) 0.19858(15) 0.0369(5) Uani 1 1 d . . .
H45A H 0.9706 0.2433 0.2006 0.044 Uiso 1 1 calc R . .
C46 C 0.7621(3) 0.31380(17) 0.15894(15) 0.0382(5) Uani 1 1 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
N1 C28 1.149(4) . ?
N2 O1 1.183(6) . ?
N2 O4 1.209(7) . ?
N2 C9 1.471(5) . ?
P1 C37 1.824(2) . ?
P1 C44 1.837(2) . ?
P1 C41 1.840(2) . ?
O2 C36 1.389(3) . ?
O2 C7 1.434(4) . ?
O3 C40 1.388(3) . ?
O3 C20 1.429(4) . ?
C1 C23 1.501(6) . ?
C2 C30 1.503(5) . ?
C3 C23 1.525(5) . ?
C4 C23 1.524(5) . ?
C5 C16 1.377(5) . ?
C5 C9 1.382(6) . ?
C6 C30 1.555(5) . ?
C8 C30 1.532(5) . ?
C9 C11 1.355(6) . ?
C10 C11 1.381(5) . ?
C10 C21 1.389(4) . ?
C12 C27 1.531(5) . ?
C13 C32 1.525(4) . ?
C14 C27 1.534(5) . ?
C15 C32 1.542(5) . ?
C16 C21 1.389(5) . ?
C17 C22 1.373(4) . ?
C17 C26 1.376(4) . ?
C18 C32 1.528(4) . ?
C19 C27 1.534(4) . ?
C21 C31 1.480(4) . ?
C22 C25 1.388(4) . ?
C23 C35 1.550(4) . ?
C25 C44 1.392(3) . ?
C26 C29 1.390(4) . ?
C27 C39 1.546(4) . ?
C28 C31 1.444(5) . ?
C29 C44 1.414(3) . ?
C29 C34 1.464(4) . ?
C30 C43 1.545(4) . ?
C31 C34 1.338(4) . ?
C32 C46 1.543(3) . ?
C33 C37 1.386(4) . ?
C33 C39 1.393(4) . ?
C35 C42 1.397(3) . ?
C35 C36 1.403(4) . ?
C36 C39 1.411(4) . ?
C37 C42 1.382(4) . ?
C38 C41 1.381(3) . ?
C38 C43 1.394(4) . ?
C40 C43 1.408(3) . ?
C40 C46 1.410(4) . ?
C41 C45 1.391(3) . ?
C45 C46 1.390(3) . ?

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 N2 O4 123.1(5) . . ?
O1 N2 C9 119.7(5) . . ?
O4 N2 C9 117.2(5) . . ?
C37 P1 C44 103.24(11) . . ?
C37 P1 C41 106.86(11) . . ?
C44 P1 C41 98.15(11) . . ?
C36 O2 C7 114.1(3) . . ?
C40 O3 C20 114.2(2) . . ?
C16 C5 C9 118.3(4) . . ?
C11 C9 C5 122.1(3) . . ?
C11 C9 N2 118.5(4) . . ?
C5 C9 N2 119.4(5) . . ?
C11 C10 C21 120.5(4) . . ?
C9 C11 C10 119.4(3) . . ?
C5 C16 C21 121.1(3) . . ?
C22 C17 C26 120.0(3) . . ?
C10 C21 C16 118.6(3) . . ?
C10 C21 C31 120.5(3) . . ?
C16 C21 C31 120.9(3) . . ?
C17 C22 C25 120.4(3) . . ?
C1 C23 C4 108.5(4) . . ?
C1 C23 C3 110.3(4) . . ?
C4 C23 C3 104.1(3) . . ?
C1 C23 C35 111.2(3) . . ?
C4 C23 C35 108.6(3) . . ?
C3 C23 C35 113.8(3) . . ?
C22 C25 C44 120.8(2) . . ?
C17 C26 C29 120.7(3) . . ?
C12 C27 C19 106.9(3) . . ?
C12 C27 C14 107.5(3) . . ?
C19 C27 C14 109.9(3) . . ?
C12 C27 C39 111.3(2) . . ?
C19 C27 C39 112.5(3) . . ?
C14 C27 C39 108.6(3) . . ?
N1 C28 C31 177.2(3) . . ?
C26 C29 C44 119.8(2) . . ?
C26 C29 C34 122.5(2) . . ?
C44 C29 C34 117.7(2) . . ?
C2 C30 C8 111.2(4) . . ?
C2 C30 C43 110.1(3) . . ?
C8 C30 C43 115.1(3) . . ?
C2 C30 C6 109.0(4) . . ?
C8 C30 C6 102.8(3) . . ?
C43 C30 C6 108.2(2) . . ?
C34 C31 C28 120.1(3) . . ?
C34 C31 C21 123.5(3) . . ?
C28 C31 C21 116.4(2) . . ?
C13 C32 C18 107.8(3) . . ?
C13 C32 C15 110.1(3) . . ?
C18 C32 C15 105.8(3) . . ?
C13 C32 C46 111.8(2) . . ?
C18 C32 C46 111.5(2) . . ?
C15 C32 C46 109.6(3) . . ?
C37 C33 C39 121.5(3) . . ?
C31 C34 C29 128.4(3) . . ?
C42 C35 C36 115.8(3) . . ?
C42 C35 C23 117.3(3) . . ?
C36 C35 C23 126.9(2) . . ?
O2 C36 C35 119.8(3) . . ?
O2 C36 C39 117.4(3) . . ?
C35 C36 C39 122.8(2) . . ?
C42 C37 C33 119.0(2) . . ?
C42 C37 P1 115.17(19) . . ?
C33 C37 P1 125.8(2) . . ?
C41 C38 C43 122.9(2) . . ?
C33 C39 C36 117.2(2) . . ?
C33 C39 C27 120.1(3) . . ?
C36 C39 C27 122.6(2) . . ?
O3 C40 C43 119.9(2) . . ?
O3 C40 C46 117.9(2) . . ?
C43 C40 C46 122.2(2) . . ?
C38 C41 C45 118.5(2) . . ?
C38 C41 P1 123.51(18) . . ?
C45 C41 P1 117.75(18) . . ?
C37 C42 C35 122.9(3) . . ?
C38 C43 C40 116.4(2) . . ?
C38 C43 C30 117.3(2) . . ?
C40 C43 C30 126.3(2) . . ?
C25 C44 C29 118.3(2) . . ?
C25 C44 P1 125.46(19) . . ?
C29 C44 P1 116.19(18) . . ?
C46 C45 C41 122.0(2) . . ?
C45 C46 C40 117.3(2) . . ?
C45 C46 C32 120.1(2) . . ?
C40 C46 C32 122.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        26.34
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.080
