# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_xxx
_database_code_depnum_ccdc_archive 'CCDC 1829583'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-05-29 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H32 Br O4 P'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C24 H32 Br O4 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         495.37
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   10.2150(9)
_cell_length_b                   11.4694(12)
_cell_length_c                   12.0747(13)
_cell_angle_alpha                115.285(10)
_cell_angle_beta                 93.898(8)
_cell_angle_gamma                92.846(8)
_cell_volume                     1271.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1288
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    1.705
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  0.848

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            13734
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_sigmaI/netI    0.1109
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         31.43
_reflns_number_total             7183
_reflns_number_gt                2601
_reflns_threshold_expression     >2sigma(I)

_diffrn_reflns_theta_full        31.43
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measured_fraction_theta_full 0.855
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'



#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.1337P)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     SHELXL
_refine_ls_extinction_coef       0.068(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7183
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2108
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.2998
_refine_ls_wR_factor_gt          0.1930
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.137

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br Uani 0.81186(8) 0.41935(8) 0.18445(8) 1.000 0.1288(4) . .
P1 P Uani 1.13384(11) 1.10264(13) 0.84053(15) 1.000 0.0649(5) . .
O1 O Uani 0.4778(3) 0.9720(4) 0.7499(4) 1.000 0.0732(16) . .
O2 O Uani 1.0648(3) 1.2316(3) 0.8883(4) 1.000 0.0814(14) . .
O3 O Uani 1.2679(3) 1.1130(3) 0.8092(4) 1.000 0.0808(16) . .
O4 O Uani 1.1225(3) 1.0630(4) 0.9495(4) 1.000 0.0750(14) . .
C1 C Uani 0.6103(4) 0.9816(4) 0.7389(4) 1.000 0.0495(14) . .
C2 C Uani 0.6774(4) 1.0947(4) 0.7431(4) 1.000 0.0506(14) . .
C3 C Uani 0.8119(4) 1.0923(4) 0.7345(5) 1.000 0.0539(16) . .
C4 C Uani 0.8798(4) 0.9876(4) 0.7228(5) 1.000 0.0540(16) . .
C5 C Uani 0.8092(4) 0.8781(4) 0.7170(5) 1.000 0.0554(18) . .
C6 C Uani 0.6741(4) 0.8709(4) 0.7234(4) 1.000 0.0485(14) . .
C7 C Uani 1.0259(4) 0.9882(4) 0.7139(5) 1.000 0.0578(18) . .
C8 C Uani 1.0829(4) 0.8983(5) 0.6229(5) 1.000 0.0621(18) . .
C9 C Uani 1.0187(4) 0.7874(5) 0.5149(5) 1.000 0.0579(19) . .
C10 C Uani 1.0693(5) 0.6674(5) 0.4781(6) 1.000 0.0710(19) . .
C11 C Uani 1.0085(5) 0.5589(5) 0.3804(6) 1.000 0.078(2) . .
C12 C Uani 0.8983(5) 0.5694(6) 0.3176(6) 1.000 0.076(2) . .
C13 C Uani 0.8494(5) 0.6875(6) 0.3480(6) 1.000 0.081(3) . .
C14 C Uani 0.9078(5) 0.7937(6) 0.4462(5) 1.000 0.072(2) . .
C15 C Uani 1.1282(7) 1.3485(6) 0.9835(7) 1.000 0.106(3) . .
C16 C Uani 1.1796(6) 0.9481(6) 0.9431(6) 1.000 0.091(3) . .
C17 C Uani 0.5999(4) 0.7471(5) 0.7142(5) 1.000 0.0601(19) . .
C18 C Uani 0.6878(5) 0.6362(5) 0.6843(6) 1.000 0.082(2) . .
C19 C Uani 0.5446(5) 0.7736(6) 0.8380(6) 1.000 0.084(3) . .
C20 C Uani 0.4874(5) 0.6959(5) 0.6089(6) 1.000 0.084(2) . .
C21 C Uani 0.6081(4) 1.2166(5) 0.7588(5) 1.000 0.0643(19) . .
C22 C Uani 0.5006(6) 1.1828(6) 0.6525(6) 1.000 0.090(3) . .
C23 C Uani 0.5525(5) 1.2784(5) 0.8853(6) 1.000 0.082(2) . .
C24 C Uani 0.7050(6) 1.3209(6) 0.7540(9) 1.000 0.116(4) . .
H1 H Uiso 0.446(8) 1.017(8) 0.734(8) 1.000 0.15(4) . .
H1A H Uiso 0.85440 0.80680 0.70860 1.000 0.0670 calc R
H2 H Uiso 0.85870 1.16510 0.73690 1.000 0.0650 calc R
H8 H Uiso 1.17450 0.90740 0.62920 1.000 0.0740 calc R
H10 H Uiso 1.14580 0.66040 0.52040 1.000 0.0850 calc R
H11 H Uiso 1.04280 0.47920 0.35780 1.000 0.0930 calc R
H13 H Uiso 0.77650 0.69470 0.30150 1.000 0.0970 calc R
H14 H Uiso 0.87230 0.87270 0.46770 1.000 0.0860 calc R
H15A H Uiso 1.10920 1.35360 1.06220 1.000 0.1590 calc R
H15B H Uiso 1.09640 1.42130 0.97380 1.000 0.1590 calc R
H15C H Uiso 1.22160 1.34930 0.97870 1.000 0.1590 calc R
H16A H Uiso 1.14020 0.87430 0.87120 1.000 0.1370 calc R
H16B H Uiso 1.16380 0.93620 1.01520 1.000 0.1370 calc R
H16C H Uiso 1.27270 0.95710 0.93850 1.000 0.1370 calc R
H18A H Uiso 0.72440 0.61900 0.60830 1.000 0.1220 calc R
H18B H Uiso 0.63670 0.56020 0.67670 1.000 0.1220 calc R
H18C H Uiso 0.75770 0.65970 0.74920 1.000 0.1220 calc R
H19A H Uiso 0.61450 0.81040 0.90350 1.000 0.1260 calc R
H19B H Uiso 0.50720 0.69390 0.83530 1.000 0.1260 calc R
H19C H Uiso 0.47790 0.83310 0.85210 1.000 0.1260 calc R
H20A H Uiso 0.42380 0.75860 0.62540 1.000 0.1270 calc R
H20B H Uiso 0.44590 0.61630 0.60300 1.000 0.1270 calc R
H20C H Uiso 0.52260 0.68100 0.53270 1.000 0.1270 calc R
H22A H Uiso 0.43630 1.11900 0.65280 1.000 0.1340 calc R
H22B H Uiso 0.53930 1.14880 0.57580 1.000 0.1340 calc R
H22C H Uiso 0.45880 1.25920 0.66210 1.000 0.1340 calc R
H23A H Uiso 0.50910 1.35320 0.89240 1.000 0.1230 calc R
H23B H Uiso 0.62330 1.30360 0.94960 1.000 0.1230 calc R
H23C H Uiso 0.49060 1.21670 0.89230 1.000 0.1230 calc R
H24A H Uiso 0.74220 1.28680 0.67650 1.000 0.1730 calc R
H24B H Uiso 0.77410 1.34600 0.81980 1.000 0.1730 calc R
H24C H Uiso 0.65920 1.39490 0.76250 1.000 0.1730 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.902(7) . . yes
P1 O2 1.565(4) . . yes
P1 O3 1.458(3) . . yes
P1 O4 1.574(5) . . yes
P1 C7 1.786(5) . . yes
O1 C1 1.373(5) . . yes
O2 C15 1.426(9) . . yes
O4 C16 1.442(9) . . yes
O1 H1 0.71(10) . . no
C1 C2 1.416(7) . . no
C1 C6 1.403(7) . . no
C2 C21 1.543(8) . . no
C2 C3 1.386(6) . . no
C3 C4 1.376(7) . . no
C4 C7 1.503(6) . . no
C4 C5 1.389(7) . . no
C5 C6 1.388(6) . . no
C6 C17 1.533(8) . . no
C7 C8 1.337(7) . . no
C8 C9 1.460(8) . . no
C9 C10 1.392(9) . . no
C9 C14 1.381(7) . . no
C10 C11 1.377(9) . . no
C11 C12 1.354(8) . . no
C12 C13 1.374(10) . . no
C13 C14 1.358(9) . . no
C17 C19 1.546(8) . . no
C17 C20 1.542(8) . . no
C17 C18 1.523(8) . . no
C21 C23 1.546(8) . . no
C21 C24 1.537(9) . . no
C21 C22 1.531(8) . . no
C3 H2 0.9300 . . no
C5 H1A 0.9300 . . no
C8 H8 0.9300 . . no
C10 H10 0.9300 . . no
C11 H11 0.9300 . . no
C13 H13 0.9300 . . no
C14 H14 0.9300 . . no
C15 H15A 0.9600 . . no
C15 H15B 0.9600 . . no
C15 H15C 0.9600 . . no
C16 H16A 0.9600 . . no
C16 H16B 0.9600 . . no
C16 H16C 0.9600 . . no
C18 H18A 0.9600 . . no
C18 H18B 0.9600 . . no
C18 H18C 0.9600 . . no
C19 H19A 0.9600 . . no
C19 H19B 0.9600 . . no
C19 H19C 0.9600 . . no
C20 H20A 0.9600 . . no
C20 H20B 0.9600 . . no
C20 H20C 0.9600 . . no
C22 H22A 0.9600 . . no
C22 H22B 0.9600 . . no
C22 H22C 0.9600 . . no
C23 H23A 0.9600 . . no
C23 H23B 0.9600 . . no
C23 H23C 0.9600 . . no
C24 H24A 0.9600 . . no
C24 H24B 0.9600 . . no
C24 H24C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O3 115.1(2) . . . yes
O2 P1 O4 101.5(2) . . . yes
O2 P1 C7 105.6(2) . . . yes
O3 P1 O4 114.3(2) . . . yes
O3 P1 C7 112.9(2) . . . yes
O4 P1 C7 106.4(2) . . . yes
P1 O2 C15 121.4(4) . . . yes
P1 O4 C16 119.2(4) . . . yes
C1 O1 H1 110(7) . . . no
O1 C1 C2 122.5(4) . . . yes
O1 C1 C6 114.8(4) . . . yes
C2 C1 C6 122.6(4) . . . no
C1 C2 C21 123.1(4) . . . no
C3 C2 C21 120.5(4) . . . no
C1 C2 C3 116.4(4) . . . no
C2 C3 C4 123.3(5) . . . no
C3 C4 C5 118.2(4) . . . no
C3 C4 C7 122.0(4) . . . no
C5 C4 C7 119.9(4) . . . no
C4 C5 C6 122.7(5) . . . no
C1 C6 C17 122.3(4) . . . no
C5 C6 C17 120.9(4) . . . no
C1 C6 C5 116.8(4) . . . no
P1 C7 C4 119.0(4) . . . yes
C4 C7 C8 124.1(5) . . . no
P1 C7 C8 116.4(3) . . . yes
C7 C8 C9 127.8(4) . . . no
C8 C9 C14 123.6(5) . . . no
C10 C9 C14 117.1(5) . . . no
C8 C9 C10 119.4(5) . . . no
C9 C10 C11 121.4(5) . . . no
C10 C11 C12 119.4(6) . . . no
Br1 C12 C11 119.6(5) . . . yes
Br1 C12 C13 119.7(4) . . . yes
C11 C12 C13 120.7(6) . . . no
C12 C13 C14 119.8(6) . . . no
C9 C14 C13 121.7(6) . . . no
C6 C17 C18 112.4(4) . . . no
C6 C17 C19 109.6(5) . . . no
C18 C17 C19 108.0(5) . . . no
C18 C17 C20 104.9(5) . . . no
C6 C17 C20 111.6(5) . . . no
C19 C17 C20 110.2(4) . . . no
C2 C21 C23 111.1(5) . . . no
C2 C21 C24 111.2(4) . . . no
C2 C21 C22 109.9(5) . . . no
C22 C21 C24 106.4(6) . . . no
C23 C21 C24 106.4(5) . . . no
C22 C21 C23 111.8(4) . . . no
C2 C3 H2 118.00 . . . no
C4 C3 H2 118.00 . . . no
C4 C5 H1A 119.00 . . . no
C6 C5 H1A 119.00 . . . no
C7 C8 H8 116.00 . . . no
C9 C8 H8 116.00 . . . no
C9 C10 H10 119.00 . . . no
C11 C10 H10 119.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 120.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C9 C14 H14 119.00 . . . no
C13 C14 H14 119.00 . . . no
O2 C15 H15A 109.00 . . . no
O2 C15 H15B 109.00 . . . no
O2 C15 H15C 109.00 . . . no
H15A C15 H15B 109.00 . . . no
H15A C15 H15C 109.00 . . . no
H15B C15 H15C 109.00 . . . no
O4 C16 H16A 109.00 . . . no
O4 C16 H16B 110.00 . . . no
O4 C16 H16C 109.00 . . . no
H16A C16 H16B 109.00 . . . no
H16A C16 H16C 109.00 . . . no
H16B C16 H16C 109.00 . . . no
C17 C18 H18A 109.00 . . . no
C17 C18 H18B 109.00 . . . no
C17 C18 H18C 109.00 . . . no
H18A C18 H18B 110.00 . . . no
H18A C18 H18C 109.00 . . . no
H18B C18 H18C 109.00 . . . no
C17 C19 H19A 109.00 . . . no
C17 C19 H19B 109.00 . . . no
C17 C19 H19C 109.00 . . . no
H19A C19 H19B 109.00 . . . no
H19A C19 H19C 109.00 . . . no
H19B C19 H19C 110.00 . . . no
C17 C20 H20A 109.00 . . . no
C17 C20 H20B 109.00 . . . no
C17 C20 H20C 109.00 . . . no
H20A C20 H20B 110.00 . . . no
H20A C20 H20C 109.00 . . . no
H20B C20 H20C 109.00 . . . no
C21 C22 H22A 109.00 . . . no
C21 C22 H22B 109.00 . . . no
C21 C22 H22C 110.00 . . . no
H22A C22 H22B 109.00 . . . no
H22A C22 H22C 109.00 . . . no
H22B C22 H22C 109.00 . . . no
C21 C23 H23A 109.00 . . . no
C21 C23 H23B 109.00 . . . no
C21 C23 H23C 109.00 . . . no
H23A C23 H23B 109.00 . . . no
H23A C23 H23C 109.00 . . . no
H23B C23 H23C 110.00 . . . no
C21 C24 H24A 109.00 . . . no
C21 C24 H24B 109.00 . . . no
C21 C24 H24C 109.00 . . . no
H24A C24 H24B 109.00 . . . no
H24A C24 H24C 109.00 . . . no
H24B C24 H24C 110.00 . . . no

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
O3 P1 O2 C15 -49.6(5) . . . . no
O4 P1 O2 C15 74.4(5) . . . . no
C7 P1 O2 C15 -174.7(5) . . . . no
O2 P1 O4 C16 -178.0(4) . . . . no
O3 P1 O4 C16 -53.5(5) . . . . no
C7 P1 O4 C16 71.7(4) . . . . no
O4 P1 C7 C4 67.3(4) . . . . no
O2 P1 C7 C4 -40.0(5) . . . . no
O3 P1 C7 C4 -166.6(4) . . . . no
O4 P1 C7 C8 -105.0(5) . . . . no
O2 P1 C7 C8 147.7(4) . . . . no
O3 P1 C7 C8 21.1(5) . . . . no
O1 C1 C2 C3 178.1(4) . . . . no
C2 C1 C6 C17 -177.7(4) . . . . no
C2 C1 C6 C5 2.5(7) . . . . no
C6 C1 C2 C21 179.4(4) . . . . no
O1 C1 C2 C21 -0.7(7) . . . . no
C6 C1 C2 C3 -1.8(7) . . . . no
O1 C1 C6 C5 -177.4(4) . . . . no
O1 C1 C6 C17 2.4(6) . . . . no
C21 C2 C3 C4 178.7(5) . . . . no
C1 C2 C3 C4 -0.2(7) . . . . no
C1 C2 C21 C24 -177.4(5) . . . . no
C1 C2 C21 C22 -59.9(6) . . . . no
C1 C2 C21 C23 64.3(6) . . . . no
C3 C2 C21 C24 3.8(7) . . . . no
C3 C2 C21 C22 121.3(5) . . . . no
C3 C2 C21 C23 -114.5(5) . . . . no
C2 C3 C4 C5 1.3(8) . . . . no
C2 C3 C4 C7 -179.9(5) . . . . no
C5 C4 C7 C8 53.2(8) . . . . no
C7 C4 C5 C6 -179.3(5) . . . . no
C3 C4 C5 C6 -0.5(8) . . . . no
C5 C4 C7 P1 -118.5(5) . . . . no
C3 C4 C7 P1 62.7(7) . . . . no
C3 C4 C7 C8 -125.6(6) . . . . no
C4 C5 C6 C1 -1.3(7) . . . . no
C4 C5 C6 C17 178.9(5) . . . . no
C5 C6 C17 C20 -123.7(5) . . . . no
C1 C6 C17 C18 174.0(5) . . . . no
C1 C6 C17 C19 -65.8(6) . . . . no
C1 C6 C17 C20 56.5(6) . . . . no
C5 C6 C17 C18 -6.2(7) . . . . no
C5 C6 C17 C19 114.0(5) . . . . no
P1 C7 C8 C9 174.1(5) . . . . no
C4 C7 C8 C9 2.2(10) . . . . no
C7 C8 C9 C10 -136.5(6) . . . . no
C7 C8 C9 C14 42.8(9) . . . . no
C8 C9 C10 C11 176.9(5) . . . . no
C14 C9 C10 C11 -2.4(9) . . . . no
C8 C9 C14 C13 -178.5(6) . . . . no
C10 C9 C14 C13 0.8(9) . . . . no
C9 C10 C11 C12 1.0(9) . . . . no
C10 C11 C12 Br1 -178.8(5) . . . . no
C10 C11 C12 C13 2.1(10) . . . . no
Br1 C12 C13 C14 177.3(5) . . . . no
C11 C12 C13 C14 -3.6(10) . . . . no
C12 C13 C14 C9 2.2(9) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 H23B 3.0500 . 1_544 no
Br1 H16A 3.2100 . 2_766 no
O1 O3 2.700(5) . 1_455 no
O1 C19 2.983(9) . . no
O1 C20 2.896(8) . . no
O1 C22 3.113(9) . . no
O1 C23 3.203(8) . . no
O2 C3 3.013(6) . . no
O3 C22 3.404(8) . 1_655 no
O3 O1 2.700(5) . 1_655 no
O3 C23 3.240(7) . 1_655 no
O1 H22A 2.4700 . . no
O1 H20A 2.2700 . . no
O1 H23C 2.5800 . . no
O1 H19C 2.4000 . . no
O2 H2 2.5500 . . no
O3 H1 2.22(8) . 1_655 no
O3 H8 2.5100 . . no
O3 H15C 2.7000 . . no
O3 H16C 2.8300 . . no
O3 H22A 2.6600 . 1_655 no
O3 H23C 2.4500 . 1_655 no
C3 O2 3.013(6) . . no
C4 C14 3.167(8) . . no
C5 C14 3.238(8) . . no
C5 C9 3.222(7) . . no
C9 C5 3.222(7) . . no
C14 C5 3.238(8) . . no
C14 C4 3.167(8) . . no
C19 O1 2.983(9) . . no
C20 O1 2.896(8) . . no
C22 O3 3.404(8) . 1_455 no
C22 O1 3.113(9) . . no
C23 O1 3.203(8) . . no
C23 O3 3.240(7) . 1_455 no
C1 H22A 2.8500 . . no
C1 H23C 2.9300 . . no
C1 H19C 2.9300 . . no
C1 H20A 2.8700 . . no
C3 H24B 2.7000 . . no
C3 H24A 2.7200 . . no
C4 H16B 2.9700 . 2_777 no
C4 H14 2.7800 . . no
C5 H18A 2.7500 . . no
C5 H14 3.1000 . . no
C5 H16B 3.0000 . 2_777 no
C5 H18C 2.7300 . . no
C7 H14 2.9700 . . no
C7 H16A 2.9400 . . no
C8 H1A 2.9400 . . no
C9 H1A 2.9100 . . no
C10 H24A 2.9500 . 2_776 no
C18 H11 3.0900 . 2_766 no
C18 H1A 2.4300 . . no
C21 H1 2.65(9) . . no
C22 H1 2.54(10) . . no
C23 H1 2.87(9) . . no
C24 H2 2.3900 . . no
H1 O3 2.22(8) . 1_455 no
H1 C21 2.65(9) . . no
H1 C22 2.54(10) . . no
H1 C23 2.87(9) . . no
H1 H22A 1.8200 . . no
H1 H23C 2.2700 . . no
H1A C8 2.9400 . . no
H1A C9 2.9100 . . no
H1A C18 2.4300 . . no
H1A H18A 2.2700 . . no
H1A H18C 2.1600 . . no
H2 O2 2.5500 . . no
H2 C24 2.3900 . . no
H2 H24A 2.1900 . . no
H2 H24B 2.1400 . . no
H8 O3 2.5100 . . no
H8 H10 2.5500 . . no
H10 H8 2.5500 . . no
H11 C18 3.0900 . 2_766 no
H13 H22C 2.5100 . 2_676 no
H14 C4 2.7800 . . no
H14 C5 3.1000 . . no
H14 C7 2.9700 . . no
H15C O3 2.7000 . . no
H16A C7 2.9400 . . no
H16A Br1 3.2100 . 2_766 no
H16B C4 2.9700 . 2_777 no
H16B C5 3.0000 . 2_777 no
H16C O3 2.8300 . . no
H18A C5 2.7500 . . no
H18A H1A 2.2700 . . no
H18A H20C 2.4600 . . no
H18B H19B 2.4100 . . no
H18B H20B 2.3200 . . no
H18B H24C 2.5300 . 1_545 no
H18C C5 2.7300 . . no
H18C H1A 2.1600 . . no
H18C H19A 2.5400 . . no
H19A H18C 2.5400 . . no
H19B H18B 2.4100 . . no
H19B H20B 2.5700 . . no
H19C O1 2.4000 . . no
H19C C1 2.9300 . . no
H19C H20A 2.5100 . . no
H20A O1 2.2700 . . no
H20A C1 2.8700 . . no
H20A H19C 2.5100 . . no
H20B H18B 2.3200 . . no
H20B H19B 2.5700 . . no
H20C H18A 2.4600 . . no
H22A O1 2.4700 . . no
H22A O3 2.6600 . 1_455 no
H22A C1 2.8500 . . no
H22A H1 1.8200 . . no
H22B H24A 2.4400 . . no
H22C H23A 2.5200 . . no
H22C H24C 2.4100 . . no
H22C H13 2.5100 . 2_676 no
H23A H22C 2.5200 . . no
H23A H24C 2.4400 . . no
H23B Br1 3.0500 . 1_566 no
H23B H24B 2.4400 . . no
H23C O1 2.5800 . . no
H23C O3 2.4500 . 1_455 no
H23C C1 2.9300 . . no
H23C H1 2.2700 . . no
H24A C3 2.7200 . . no
H24A H2 2.1900 . . no
H24A H22B 2.4400 . . no
H24A C10 2.9500 . 2_776 no
H24B C3 2.7000 . . no
H24B H2 2.1400 . . no
H24B H23B 2.4400 . . no
H24C H18B 2.5300 . 1_565 no
H24C H22C 2.4100 . . no
H24C H23A 2.4400 . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1 O3 0.71(10) 2.22(8) 2.700(5) 127(9) 1_455 yes
C3 H2 O2 0.9300 2.5500 3.013(6) 111.00 . yes
C8 H8 O3 0.9300 2.5100 2.987(7) 112.00 . yes
C19 H19C O1 0.9600 2.4000 2.983(9) 119.00 . yes
C20 H20A O1 0.9600 2.2700 2.896(8) 122.00 . yes
C22 H22A O1 0.9600 2.4700 3.113(9) 124.00 . yes
C23 H23C O1 0.9600 2.5800 3.203(8) 123.00 . yes
C23 H23C O3 0.9600 2.4500 3.240(7) 139.00 1_455 yes

####################################################################
#                         END of data
####################################################################

####################################################################### 
# 
# 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_xxx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1829589'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-05-29 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H39 N2 O4 P'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C27 H39 N2 O4 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         486.57
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   9.947(3)
_cell_length_b                   15.743(4)
_cell_length_c                   18.185(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2847.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3592
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.4

_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.320
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.960

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            19374
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.39
_reflns_number_total             5157
_reflns_number_gt                3647
_reflns_threshold_expression     >2sigma(I)

_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'



#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0705P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.19(12)
_refine_ls_number_reflns         5157
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.060

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P Uani 0.95288(9) 0.62490(6) 0.76149(4) 1.000 0.0666(3) . .
O1 O Uani 0.8997(3) 0.45575(14) 1.17578(12) 1.000 0.0631(8) . .
O2 O Uani 1.0877(3) 0.5754(2) 0.76990(16) 1.000 0.1231(13) . .
O3 O Uani 0.8589(2) 0.59173(17) 0.70751(12) 1.000 0.0868(10) . .
O4 O Uani 1.0074(3) 0.7163(2) 0.74528(14) 1.000 0.0939(10) . .
N1 N Uani 0.7660(3) 0.59597(17) 0.85783(14) 1.000 0.0650(10) . .
N2 N Uani 0.6618(4) 0.5707(3) 0.86489(19) 1.000 0.1053(14) . .
C1 C Uani 0.9100(3) 0.50483(16) 1.11291(15) 1.000 0.0474(9) . .
C2 C Uani 0.9308(3) 0.46415(16) 1.04469(15) 1.000 0.0481(9) . .
C3 C Uani 0.9437(3) 0.51671(16) 0.98324(14) 1.000 0.0487(9) . .
C4 C Uani 0.9375(3) 0.60434(16) 0.98711(13) 1.000 0.0423(8) . .
C5 C Uani 0.9221(2) 0.64164(16) 1.05535(13) 1.000 0.0424(8) . .
C6 C Uani 0.9094(3) 0.59391(16) 1.11990(13) 1.000 0.0448(8) . .
C7 C Uani 0.9632(3) 0.65861(15) 0.91807(13) 1.000 0.0445(8) . .
C8 C Uani 0.9403(3) 0.75306(15) 0.93056(12) 1.000 0.0419(8) . .
C9 C Uani 1.0473(3) 0.80643(17) 0.94466(15) 1.000 0.0499(9) . .
C10 C Uani 1.0279(3) 0.89076(18) 0.96343(16) 1.000 0.0567(10) . .
C11 C Uani 0.8997(3) 0.92431(17) 0.96884(15) 1.000 0.0529(10) . .
C12 C Uani 0.7933(3) 0.87194(19) 0.95217(16) 1.000 0.0571(10) . .
C13 C Uani 0.8124(3) 0.78802(18) 0.93335(16) 1.000 0.0524(10) . .
C14 C Uani 0.8884(3) 0.62512(18) 0.85071(14) 1.000 0.0506(9) . .
C15 C Uani 1.1746(8) 0.5528(6) 0.7200(4) 1.000 0.229(5) . .
C16 C Uani 0.9116(6) 0.7834(3) 0.7311(3) 1.000 0.122(2) . .
C17 C Uani 0.8721(4) 1.0145(2) 0.9963(2) 1.000 0.0773(16) . .
C18 C Uani 0.9862(6) 1.0745(2) 0.9865(3) 1.000 0.131(2) . .
C19 C Uani 0.8252(4) 1.0113(2) 1.0759(2) 1.000 0.0920(17) . .
C20 C Uani 0.8993(3) 0.63888(18) 1.19537(15) 1.000 0.0579(10) . .
C21 C Uani 0.9088(5) 0.7363(2) 1.18674(19) 1.000 0.0893(16) . .
C22 C Uani 0.7657(4) 0.6196(2) 1.23263(19) 1.000 0.0830(16) . .
C23 C Uani 1.0168(4) 0.6109(2) 1.2443(2) 1.000 0.0913(16) . .
C24 C Uani 0.9426(3) 0.36685(17) 1.03738(17) 1.000 0.0593(10) . .
C25 C Uani 0.8124(4) 0.3224(2) 1.0590(2) 1.000 0.0907(16) . .
C26 C Uani 1.0589(4) 0.3337(2) 1.0854(3) 1.000 0.0923(16) . .
C27 C Uani 0.9764(5) 0.3406(2) 0.9586(2) 1.000 0.0961(18) . .
H1 H Uiso 0.824(4) 0.449(2) 1.183(2) 1.000 0.077(13) . .
H3 H Uiso 0.95700 0.49160 0.93750 1.000 0.0580 calc R
H5 H Uiso 0.92010 0.70060 1.05850 1.000 0.0510 calc R
H7 H Uiso 1.05910 0.65240 0.90700 1.000 0.0530 calc R
H9 H Uiso 1.13440 0.78530 0.94150 1.000 0.0600 calc R
H10 H Uiso 1.10190 0.92530 0.97250 1.000 0.0680 calc R
H12 H Uiso 0.70640 0.89370 0.95360 1.000 0.0690 calc R
H13 H Uiso 0.73840 0.75430 0.92230 1.000 0.0630 calc R
H15A H Uiso 1.15550 0.58200 0.67480 1.000 0.3440 calc R
H15B H Uiso 1.16860 0.49260 0.71200 1.000 0.3440 calc R
H15C H Uiso 1.26360 0.56700 0.73620 1.000 0.3440 calc R
H16A H Uiso 0.84230 0.78200 0.76790 1.000 0.1830 calc R
H16B H Uiso 0.87230 0.77540 0.68340 1.000 0.1830 calc R
H16C H Uiso 0.95660 0.83730 0.73280 1.000 0.1830 calc R
H17 H Uiso 0.79700 1.03660 0.96720 1.000 0.0930 calc R
H18A H Uiso 1.01100 1.07660 0.93550 1.000 0.1960 calc R
H18B H Uiso 1.06160 1.05550 1.01510 1.000 0.1960 calc R
H18C H Uiso 0.95970 1.13010 1.00260 1.000 0.1960 calc R
H19A H Uiso 0.80490 1.06780 1.09250 1.000 0.1380 calc R
H19B H Uiso 0.89500 0.98760 1.10600 1.000 0.1380 calc R
H19C H Uiso 0.74610 0.97660 1.07940 1.000 0.1380 calc R
H21A H Uiso 0.99270 0.75080 1.16380 1.000 0.1340 calc R
H21B H Uiso 0.90380 0.76260 1.23430 1.000 0.1340 calc R
H21C H Uiso 0.83590 0.75610 1.15670 1.000 0.1340 calc R
H22A H Uiso 0.75640 0.55940 1.23880 1.000 0.1250 calc R
H22B H Uiso 0.69350 0.64060 1.20270 1.000 0.1250 calc R
H22C H Uiso 0.76310 0.64680 1.27990 1.000 0.1250 calc R
H23A H Uiso 1.10020 0.62380 1.22030 1.000 0.1370 calc R
H23B H Uiso 1.01110 0.55080 1.25290 1.000 0.1370 calc R
H23C H Uiso 1.01250 0.64050 1.29040 1.000 0.1370 calc R
H25A H Uiso 0.82350 0.26200 1.05430 1.000 0.1360 calc R
H25B H Uiso 0.74100 0.34090 1.02730 1.000 0.1360 calc R
H25C H Uiso 0.79050 0.33610 1.10900 1.000 0.1360 calc R
H26A H Uiso 1.06490 0.27310 1.08060 1.000 0.1380 calc R
H26B H Uiso 1.04250 0.34830 1.13580 1.000 0.1380 calc R
H26C H Uiso 1.14170 0.35910 1.06950 1.000 0.1380 calc R
H27A H Uiso 0.98330 0.27980 0.95590 1.000 0.1440 calc R
H27B H Uiso 1.06040 0.36570 0.94440 1.000 0.1440 calc R
H27C H Uiso 0.90670 0.35980 0.92610 1.000 0.1440 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.559(3) . . yes
P1 O3 1.453(2) . . yes
P1 O4 1.566(3) . . yes
P1 C14 1.745(3) . . yes
O1 C1 1.384(3) . . yes
O2 C15 1.303(8) . . yes
O4 C16 1.446(6) . . yes
O1 H1 0.77(4) . . no
N1 C14 1.308(4) . . yes
N1 N2 1.118(5) . . yes
C1 C2 1.411(4) . . no
C1 C6 1.408(4) . . no
C2 C3 1.396(4) . . no
C2 C24 1.542(4) . . no
C3 C4 1.383(4) . . no
C4 C7 1.540(3) . . no
C4 C5 1.381(3) . . no
C5 C6 1.400(3) . . no
C6 C20 1.548(4) . . no
C7 C8 1.521(3) . . no
C7 C14 1.527(4) . . no
C8 C13 1.387(4) . . no
C8 C9 1.380(4) . . no
C9 C10 1.384(4) . . no
C10 C11 1.384(4) . . no
C11 C12 1.375(4) . . no
C11 C17 1.530(4) . . no
C12 C13 1.378(4) . . no
C17 C18 1.487(6) . . no
C17 C19 1.522(5) . . no
C20 C22 1.522(5) . . no
C20 C23 1.534(5) . . no
C20 C21 1.545(4) . . no
C24 C26 1.541(5) . . no
C24 C27 1.529(5) . . no
C24 C25 1.524(5) . . no
C3 H3 0.9300 . . no
C5 H5 0.9300 . . no
C7 H7 0.9800 . . no
C9 H9 0.9300 . . no
C10 H10 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C15 H15A 0.9600 . . no
C15 H15B 0.9600 . . no
C15 H15C 0.9600 . . no
C16 H16A 0.9600 . . no
C16 H16B 0.9600 . . no
C16 H16C 0.9600 . . no
C17 H17 0.9800 . . no
C18 H18A 0.9600 . . no
C18 H18B 0.9600 . . no
C18 H18C 0.9600 . . no
C19 H19A 0.9600 . . no
C19 H19B 0.9600 . . no
C19 H19C 0.9600 . . no
C21 H21A 0.9600 . . no
C21 H21B 0.9600 . . no
C21 H21C 0.9600 . . no
C22 H22A 0.9600 . . no
C22 H22B 0.9600 . . no
C22 H22C 0.9600 . . no
C23 H23A 0.9600 . . no
C23 H23B 0.9600 . . no
C23 H23C 0.9600 . . no
C25 H25A 0.9600 . . no
C25 H25B 0.9600 . . no
C25 H25C 0.9600 . . no
C26 H26A 0.9600 . . no
C26 H26B 0.9600 . . no
C26 H26C 0.9600 . . no
C27 H27A 0.9600 . . no
C27 H27B 0.9600 . . no
C27 H27C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O3 116.12(16) . . . yes
O2 P1 O4 100.37(17) . . . yes
O2 P1 C14 103.07(15) . . . yes
O3 P1 O4 115.22(15) . . . yes
O3 P1 C14 113.11(14) . . . yes
O4 P1 C14 107.49(14) . . . yes
P1 O2 C15 129.7(4) . . . yes
P1 O4 C16 118.5(3) . . . yes
C1 O1 H1 107(3) . . . no
N2 N1 C14 179.0(3) . . . yes
O1 C1 C6 118.8(2) . . . yes
C2 C1 C6 122.1(2) . . . no
O1 C1 C2 118.9(2) . . . yes
C1 C2 C3 116.6(2) . . . no
C3 C2 C24 120.8(2) . . . no
C1 C2 C24 122.5(2) . . . no
C2 C3 C4 123.1(2) . . . no
C3 C4 C7 120.3(2) . . . no
C5 C4 C7 121.0(2) . . . no
C3 C4 C5 118.4(2) . . . no
C4 C5 C6 122.4(2) . . . no
C1 C6 C20 122.4(2) . . . no
C5 C6 C20 120.3(2) . . . no
C1 C6 C5 117.3(2) . . . no
C4 C7 C14 112.4(2) . . . no
C8 C7 C14 112.6(2) . . . no
C4 C7 C8 113.3(2) . . . no
C7 C8 C13 122.1(3) . . . no
C9 C8 C13 117.3(2) . . . no
C7 C8 C9 120.5(3) . . . no
C8 C9 C10 121.5(3) . . . no
C9 C10 C11 120.8(3) . . . no
C10 C11 C12 117.7(3) . . . no
C12 C11 C17 119.4(3) . . . no
C10 C11 C17 122.9(3) . . . no
C11 C12 C13 121.6(3) . . . no
C8 C13 C12 121.1(3) . . . no
P1 C14 C7 124.6(2) . . . yes
N1 C14 C7 119.7(2) . . . yes
P1 C14 N1 115.7(2) . . . yes
C11 C17 C19 109.6(3) . . . no
C18 C17 C19 111.7(3) . . . no
C11 C17 C18 114.4(3) . . . no
C6 C20 C21 111.1(2) . . . no
C6 C20 C22 111.1(2) . . . no
C21 C20 C22 107.3(3) . . . no
C21 C20 C23 107.3(3) . . . no
C6 C20 C23 109.5(2) . . . no
C22 C20 C23 110.5(3) . . . no
C2 C24 C26 110.2(2) . . . no
C2 C24 C27 111.5(2) . . . no
C2 C24 C25 111.7(2) . . . no
C25 C24 C27 107.7(3) . . . no
C26 C24 C27 105.9(3) . . . no
C25 C24 C26 109.7(3) . . . no
C2 C3 H3 118.00 . . . no
C4 C3 H3 118.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C4 C7 H7 106.00 . . . no
C8 C7 H7 106.00 . . . no
C14 C7 H7 106.00 . . . no
C8 C9 H9 119.00 . . . no
C10 C9 H9 119.00 . . . no
C9 C10 H10 120.00 . . . no
C11 C10 H10 120.00 . . . no
C11 C12 H12 119.00 . . . no
C13 C12 H12 119.00 . . . no
C8 C13 H13 119.00 . . . no
C12 C13 H13 119.00 . . . no
O2 C15 H15A 110.00 . . . no
O2 C15 H15B 109.00 . . . no
O2 C15 H15C 110.00 . . . no
H15A C15 H15B 109.00 . . . no
H15A C15 H15C 109.00 . . . no
H15B C15 H15C 109.00 . . . no
O4 C16 H16A 109.00 . . . no
O4 C16 H16B 109.00 . . . no
O4 C16 H16C 109.00 . . . no
H16A C16 H16B 110.00 . . . no
H16A C16 H16C 109.00 . . . no
H16B C16 H16C 110.00 . . . no
C11 C17 H17 107.00 . . . no
C18 C17 H17 107.00 . . . no
C19 C17 H17 107.00 . . . no
C17 C18 H18A 109.00 . . . no
C17 C18 H18B 109.00 . . . no
C17 C18 H18C 109.00 . . . no
H18A C18 H18B 109.00 . . . no
H18A C18 H18C 109.00 . . . no
H18B C18 H18C 109.00 . . . no
C17 C19 H19A 109.00 . . . no
C17 C19 H19B 109.00 . . . no
C17 C19 H19C 109.00 . . . no
H19A C19 H19B 109.00 . . . no
H19A C19 H19C 109.00 . . . no
H19B C19 H19C 110.00 . . . no
C20 C21 H21A 109.00 . . . no
C20 C21 H21B 109.00 . . . no
C20 C21 H21C 110.00 . . . no
H21A C21 H21B 109.00 . . . no
H21A C21 H21C 109.00 . . . no
H21B C21 H21C 109.00 . . . no
C20 C22 H22A 109.00 . . . no
C20 C22 H22B 109.00 . . . no
C20 C22 H22C 109.00 . . . no
H22A C22 H22B 110.00 . . . no
H22A C22 H22C 109.00 . . . no
H22B C22 H22C 109.00 . . . no
C20 C23 H23A 110.00 . . . no
C20 C23 H23B 109.00 . . . no
C20 C23 H23C 109.00 . . . no
H23A C23 H23B 109.00 . . . no
H23A C23 H23C 109.00 . . . no
H23B C23 H23C 109.00 . . . no
C24 C25 H25A 109.00 . . . no
C24 C25 H25B 110.00 . . . no
C24 C25 H25C 110.00 . . . no
H25A C25 H25B 109.00 . . . no
H25A C25 H25C 109.00 . . . no
H25B C25 H25C 109.00 . . . no
C24 C26 H26A 109.00 . . . no
C24 C26 H26B 109.00 . . . no
C24 C26 H26C 109.00 . . . no
H26A C26 H26B 110.00 . . . no
H26A C26 H26C 109.00 . . . no
H26B C26 H26C 110.00 . . . no
C24 C27 H27A 109.00 . . . no
C24 C27 H27B 109.00 . . . no
C24 C27 H27C 109.00 . . . no
H27A C27 H27B 110.00 . . . no
H27A C27 H27C 110.00 . . . no
H27B C27 H27C 109.00 . . . no

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
O3 P1 O2 C15 52.2(6) . . . . no
O4 P1 O2 C15 -72.7(6) . . . . no
C14 P1 O2 C15 176.4(6) . . . . no
O2 P1 O4 C16 177.9(3) . . . . no
O3 P1 O4 C16 52.4(3) . . . . no
C14 P1 O4 C16 -74.7(3) . . . . no
O4 P1 C14 N1 128.4(2) . . . . no
O2 P1 C14 N1 -126.2(2) . . . . no
O3 P1 C14 N1 0.0(3) . . . . no
O4 P1 C14 C7 -49.9(3) . . . . no
O2 P1 C14 C7 55.6(3) . . . . no
O3 P1 C14 C7 -178.3(2) . . . . no
O1 C1 C2 C3 -178.5(3) . . . . no
C2 C1 C6 C20 -174.4(3) . . . . no
O1 C1 C2 C24 0.0(4) . . . . no
C6 C1 C2 C3 -3.4(4) . . . . no
C6 C1 C2 C24 175.1(3) . . . . no
O1 C1 C6 C5 179.0(3) . . . . no
O1 C1 C6 C20 0.7(4) . . . . no
C2 C1 C6 C5 3.9(4) . . . . no
C3 C2 C24 C26 120.5(3) . . . . no
C3 C2 C24 C27 3.2(4) . . . . no
C1 C2 C3 C4 0.3(4) . . . . no
C24 C2 C3 C4 -178.2(3) . . . . no
C1 C2 C24 C25 64.2(4) . . . . no
C1 C2 C24 C26 -58.0(4) . . . . no
C1 C2 C24 C27 -175.3(3) . . . . no
C3 C2 C24 C25 -117.4(3) . . . . no
C2 C3 C4 C5 2.1(4) . . . . no
C2 C3 C4 C7 175.4(3) . . . . no
C5 C4 C7 C8 -12.0(4) . . . . no
C3 C4 C5 C6 -1.6(4) . . . . no
C7 C4 C5 C6 -174.8(3) . . . . no
C3 C4 C7 C8 174.9(3) . . . . no
C3 C4 C7 C14 45.8(4) . . . . no
C5 C4 C7 C14 -141.1(3) . . . . no
C4 C5 C6 C1 -1.3(4) . . . . no
C4 C5 C6 C20 177.0(3) . . . . no
C5 C6 C20 C21 -1.4(4) . . . . no
C5 C6 C20 C22 118.0(3) . . . . no
C5 C6 C20 C23 -119.7(3) . . . . no
C1 C6 C20 C21 176.9(3) . . . . no
C1 C6 C20 C22 -63.8(4) . . . . no
C1 C6 C20 C23 58.5(4) . . . . no
C8 C7 C14 P1 88.3(3) . . . . no
C4 C7 C8 C9 98.3(3) . . . . no
C4 C7 C8 C13 -77.2(3) . . . . no
C14 C7 C8 C9 -132.8(3) . . . . no
C14 C7 C8 C13 51.8(3) . . . . no
C4 C7 C14 P1 -142.2(2) . . . . no
C4 C7 C14 N1 39.6(4) . . . . no
C8 C7 C14 N1 -89.9(3) . . . . no
C7 C8 C9 C10 -173.5(2) . . . . no
C13 C8 C9 C10 2.3(4) . . . . no
C9 C8 C13 C12 -2.4(4) . . . . no
C7 C8 C13 C12 173.3(2) . . . . no
C8 C9 C10 C11 0.2(4) . . . . no
C9 C10 C11 C17 174.1(3) . . . . no
C9 C10 C11 C12 -2.5(4) . . . . no
C10 C11 C17 C18 24.9(5) . . . . no
C10 C11 C12 C13 2.4(4) . . . . no
C17 C11 C12 C13 -174.3(3) . . . . no
C12 C11 C17 C19 75.2(4) . . . . no
C10 C11 C17 C19 -101.4(4) . . . . no
C12 C11 C17 C18 -158.6(3) . . . . no
C11 C12 C13 C8 0.0(4) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C22 3.082(4) . . no
O1 C23 2.979(4) . . no
O1 C25 3.110(4) . . no
O1 C26 2.983(5) . . no
O1 O3 2.740(4) . 2_665 no
O3 O1 2.740(4) . 2_664 no
O3 N1 2.886(3) . . no
O1 H25C 2.4900 . . no
O1 H23B 2.3300 . . no
O1 H26B 2.3300 . . no
O1 H22A 2.4500 . . no
O2 H7 2.7900 . . no
O3 H1 1.98(4) . 2_664 no
O3 H22A 2.7000 . 2_664 no
O3 H25C 2.5900 . 2_664 no
O3 H18A 2.9100 . 4_746 no
O4 H15A 2.8800 . . no
N1 O3 2.886(3) . . no
N1 C3 3.144(4) . . no
N1 C13 3.353(4) . . no
N2 C10 3.448(5) . 3_467 no
N1 H3 2.9000 . . no
N1 H13 2.7700 . . no
N2 H19B 2.8600 . 3_467 no
C3 N1 3.144(4) . . no
C5 C13 3.380(4) . . no
C5 C9 3.512(4) . . no
C9 C5 3.512(4) . . no
C10 N2 3.448(5) . 3_567 no
C13 N1 3.353(4) . . no
C13 C5 3.380(4) . . no
C22 O1 3.082(4) . . no
C23 O1 2.979(4) . . no
C25 O1 3.110(4) . . no
C26 O1 2.983(5) . . no
C1 H23B 2.8300 . . no
C1 H25C 2.9100 . . no
C1 H26B 2.8300 . . no
C1 H22A 2.8800 . . no
C3 H27B 2.7400 . . no
C3 H27C 2.7100 . . no
C4 H12 2.8800 . 3_567 no
C5 H21C 2.7200 . . no
C5 H12 2.8900 . 3_567 no
C5 H21A 2.7100 . . no
C5 H9 3.0800 . 3_467 no
C8 H5 2.4800 . . no
C9 H5 2.9400 . . no
C10 H18B 2.7800 . . no
C10 H18A 2.9700 . . no
C12 H19C 2.8800 . . no
C13 H16A 3.0200 . . no
C13 H5 2.8700 . . no
C14 H13 2.8400 . . no
C14 H3 2.7200 . . no
C14 H16A 2.9300 . . no
C18 H25B 2.8700 . 3_567 no
C18 H10 2.6300 . . no
C20 H1 3.09(3) . . no
C21 H5 2.4000 . . no
C22 H1 2.89(3) . . no
C25 H1 3.01(3) . . no
C27 H3 2.4200 . . no
H1 C20 3.09(3) . . no
H1 C22 2.89(3) . . no
H1 C25 3.01(3) . . no
H1 H22A 2.1200 . . no
H1 H25C 2.2500 . . no
H1 O3 1.98(4) . 2_665 no
H3 N1 2.9000 . . no
H3 C14 2.7200 . . no
H3 C27 2.4200 . . no
H3 H27B 2.2400 . . no
H3 H27C 2.1400 . . no
H5 C8 2.4800 . . no
H5 C9 2.9400 . . no
H5 C13 2.8700 . . no
H5 C21 2.4000 . . no
H5 H21A 2.1900 . . no
H5 H21C 2.1600 . . no
H7 O2 2.7900 . . no
H7 H9 2.3100 . . no
H9 H7 2.3100 . . no
H9 C5 3.0800 . 3_567 no
H10 C18 2.6300 . . no
H10 H18B 2.2300 . . no
H12 H17 2.4400 . . no
H12 C4 2.8800 . 3_467 no
H12 C5 2.8900 . 3_467 no
H13 N1 2.7700 . . no
H13 C14 2.8400 . . no
H15A O4 2.8800 . . no
H16A C13 3.0200 . . no
H16A C14 2.9300 . . no
H17 H12 2.4400 . . no
H17 H26C 2.3500 . 3_467 no
H18A C10 2.9700 . . no
H18A O3 2.9100 . 4_756 no
H18B C10 2.7800 . . no
H18B H10 2.2300 . . no
H18B H19B 2.5700 . . no
H18B H25B 2.5400 . 3_567 no
H18C H19A 2.4500 . . no
H18C H27A 2.5200 . 1_565 no
H19A H18C 2.4500 . . no
H19B H18B 2.5700 . . no
H19B N2 2.8600 . 3_567 no
H19C C12 2.8800 . . no
H21A C5 2.7100 . . no
H21A H5 2.1900 . . no
H21A H23A 2.4900 . . no
H21B H22C 2.4400 . . no
H21B H23C 2.4300 . . no
H21C C5 2.7200 . . no
H21C H5 2.1600 . . no
H21C H22B 2.4500 . . no
H22A O1 2.4500 . . no
H22A C1 2.8800 . . no
H22A H1 2.1200 . . no
H22A H23B 2.5500 . . no
H22A O3 2.7000 . 2_665 no
H22B H21C 2.4500 . . no
H22C H21B 2.4400 . . no
H22C H23C 2.4900 . . no
H23A H21A 2.4900 . . no
H23B O1 2.3300 . . no
H23B C1 2.8300 . . no
H23B H22A 2.5500 . . no
H23C H21B 2.4300 . . no
H23C H22C 2.4900 . . no
H25A H26A 2.4500 . . no
H25A H27A 2.4100 . . no
H25B H27C 2.4900 . . no
H25B C18 2.8700 . 3_467 no
H25B H18B 2.5400 . 3_467 no
H25C O1 2.4900 . . no
H25C C1 2.9100 . . no
H25C H1 2.2500 . . no
H25C H26B 2.5600 . . no
H25C O3 2.5900 . 2_665 no
H26A H25A 2.4500 . . no
H26A H27A 2.4100 . . no
H26B O1 2.3300 . . no
H26B C1 2.8300 . . no
H26B H25C 2.5600 . . no
H26C H27B 2.4200 . . no
H26C H17 2.3500 . 3_567 no
H27A H18C 2.5200 . 1_545 no
H27A H25A 2.4100 . . no
H27A H26A 2.4100 . . no
H27B C3 2.7400 . . no
H27B H3 2.2400 . . no
H27B H26C 2.4200 . . no
H27C C3 2.7100 . . no
H27C H3 2.1400 . . no
H27C H25B 2.4900 . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1 O3 0.77(4) 1.98(4) 2.740(4) 168(3) 2_665 yes
C22 H22A O1 0.9600 2.4500 3.082(4) 123.00 . yes
C23 H23B O1 0.9600 2.3300 2.979(4) 124.00 . yes
C25 H25C O1 0.9600 2.4900 3.110(4) 122.00 . yes
C25 H25C O3 0.9600 2.5900 3.468(4) 152.00 2_665 yes
C26 H26B O1 0.9600 2.3300 2.983(5) 125.00 . yes



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