# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_le97
_database_code_depnum_ccdc_archive 'CCDC 1495182'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-11-18 downloaded from the CCDC.
;
#compound 3b

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 N3 O2'
_chemical_formula_sum            'C23 H27 N3 O2'
_chemical_formula_weight         377.47

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'

_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                   8.2014(4)
_cell_length_b                   10.9469(6)
_cell_length_c                   12.2410(4)
_cell_angle_alpha                99.951(3)
_cell_angle_beta                 94.490(3)
_cell_angle_gamma                103.679(2)
_cell_volume                     1043.58(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    4263
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.937067
_exptl_absorpt_correction_T_max  1.07466
_exptl_absorpt_process_details   DENZO/SCALEPACK
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.0(1)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12232
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_full        25.024
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3654
_reflns_number_gt                2595
_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       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_solution    SHELXT(Sheldrick,2014)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_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)+(0.0456P)²+0.8059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3654
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4465(2) 0.79577(18) 0.20478(17) 0.0414(5) Uani 1 1 d . . . . .
O2 O -0.1789(2) 0.51555(18) 0.08385(15) 0.0380(5) Uani 1 1 d . . . . .
N1 N 0.6749(3) 0.7392(2) 0.13995(18) 0.0296(5) Uani 1 1 d . . . . .
H1 H 0.724(4) 0.679(3) 0.125(2) 0.036 Uiso 1 1 d . U . . .
N2 N 0.2552(3) 0.4153(2) 0.26044(17) 0.0273(5) Uani 1 1 d . . . . .
N3 N 0.1002(3) 0.3635(2) 0.20221(16) 0.0262(5) Uani 1 1 d . . . . .
C1 C 0.5223(3) 0.7137(3) 0.1756(2) 0.0289(6) Uani 1 1 d . . . . .
C2 C 0.7734(3) 0.8671(2) 0.1296(2) 0.0285(6) Uani 1 1 d . . . . .
C3 C 0.6731(4) 0.9221(3) 0.0486(2) 0.0388(7) Uani 1 1 d . . . . .
H3A H 0.6398 0.8612 -0.0229 0.058 Uiso 1 1 calc R U . . .
H3B H 0.7435 1.0034 0.0367 0.058 Uiso 1 1 calc R U . . .
H3C H 0.5717 0.9371 0.0801 0.058 Uiso 1 1 calc R U . . .
C4 C 0.9353(3) 0.8484(3) 0.0836(2) 0.0383(7) Uani 1 1 d . . . . .
H4A H 0.9968 0.8100 0.1346 0.057 Uiso 1 1 calc R U . . .
H4B H 1.0066 0.9316 0.0767 0.057 Uiso 1 1 calc R U . . .
H4C H 0.9067 0.7914 0.0099 0.057 Uiso 1 1 calc R U . . .
C5 C 0.8176(4) 0.9566(3) 0.2434(2) 0.0410(7) Uani 1 1 d . . . . .
H5A H 0.7134 0.9637 0.2751 0.062 Uiso 1 1 calc R U . . .
H5B H 0.8814 1.0416 0.2350 0.062 Uiso 1 1 calc R U . . .
H5C H 0.8864 0.9222 0.2933 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4428(4) 0.5726(3) 0.1735(2) 0.0293(6) Uani 1 1 d . . . . .
H6A H 0.531(4) 0.528(3) 0.189(2) 0.035 Uiso 1 1 d . U . . .
H6B H 0.382(3) 0.533(3) 0.097(2) 0.035 Uiso 1 1 d . U . . .
C7 C 0.3173(3) 0.5539(2) 0.2588(2) 0.0252(6) Uani 1 1 d . . . . .
H7 H 0.371(3) 0.602(3) 0.336(2) 0.030 Uiso 1 1 d . U . . .
C8 C 0.0380(3) 0.4555(2) 0.1776(2) 0.0255(6) Uani 1 1 d . . . . .
C9 C -0.1297(3) 0.4276(3) 0.1142(2) 0.0283(6) Uani 1 1 d . . . . .
C10 C -0.2390(4) 0.2931(3) 0.0888(2) 0.0395(7) Uani 1 1 d . . . . .
H10A H -0.3323 0.2870 0.1347 0.059 Uiso 1 1 calc R U . . .
H10B H -0.1715 0.2343 0.1056 0.059 Uiso 1 1 calc R U . . .
H10C H -0.2850 0.2700 0.0096 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1486(3) 0.5873(2) 0.2268(2) 0.0249(6) Uani 1 1 d . . . . .
H11 H 0.160(3) 0.641(3) 0.174(2) 0.030 Uiso 1 1 d . U . . .
C12 C 0.0819(3) 0.6552(2) 0.3266(2) 0.0260(6) Uani 1 1 d . . . . .
C13 C 0.1495(4) 0.7858(3) 0.3658(2) 0.0337(6) Uani 1 1 d . . . . .
H13 H 0.2344 0.8319 0.3291 0.040 Uiso 1 1 calc R U . . .
C14 C 0.0948(4) 0.8497(3) 0.4577(2) 0.0379(7) Uani 1 1 d . . . . .
H14 H 0.1425 0.9390 0.4837 0.046 Uiso 1 1 calc R U . . .
C15 C -0.0289(4) 0.7844(3) 0.5120(2) 0.0406(7) Uani 1 1 d . . . . .
H15 H -0.0680 0.8285 0.5743 0.049 Uiso 1 1 calc R U . . .
C16 C -0.0947(4) 0.6549(3) 0.4747(2) 0.0472(8) Uani 1 1 d . . . . .
H16 H -0.1782 0.6090 0.5124 0.057 Uiso 1 1 calc R U . . .
C17 C -0.0403(4) 0.5903(3) 0.3823(2) 0.0374(7) Uani 1 1 d . . . . .
H17 H -0.0875 0.5007 0.3572 0.045 Uiso 1 1 calc R U . . .
C18 C 0.3536(3) 0.3348(2) 0.2924(2) 0.0255(6) Uani 1 1 d . . . . .
C19 C 0.5043(3) 0.3874(3) 0.3633(2) 0.0319(6) Uani 1 1 d . . . . .
H19 H 0.5435 0.4777 0.3873 0.038 Uiso 1 1 calc R U . . .
C20 C 0.5966(4) 0.3084(3) 0.3989(2) 0.0372(7) Uani 1 1 d . . . . .
H20 H 0.6988 0.3447 0.4480 0.045 Uiso 1 1 calc R U . . .
C21 C 0.5419(4) 0.1768(3) 0.3637(2) 0.0424(8) Uani 1 1 d . . . . .
H21 H 0.6053 0.1226 0.3890 0.051 Uiso 1 1 calc R U . . .
C22 C 0.3947(4) 0.1250(3) 0.2916(2) 0.0418(7) Uani 1 1 d . . . . .
H22 H 0.3584 0.0348 0.2658 0.050 Uiso 1 1 calc R U . . .
C23 C 0.2989(3) 0.2022(3) 0.2561(2) 0.0322(6) Uani 1 1 d . . . . .
H23 H 0.1965 0.1652 0.2073 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.228(3) . ?
O2 C9 1.229(3) . ?
N1 C1 1.340(3) . ?
N1 C2 1.474(3) . ?
N1 H1 0.85(3) . ?
N2 N3 1.350(3) . ?
N2 C18 1.409(3) . ?
N2 C7 1.486(3) . ?
N3 C8 1.300(3) . ?
C1 C6 1.523(4) . ?
C2 C5 1.521(4) . ?
C2 C4 1.526(4) . ?
C2 C3 1.528(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.527(3) . ?
C6 H6A 0.99(3) . ?
C6 H6B 1.00(3) . ?
C7 C11 1.550(3) . ?
C7 H7 1.01(3) . ?
C8 C9 1.462(4) . ?
C8 C11 1.504(4) . ?
C9 C10 1.498(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.526(3) . ?
C11 H11 0.94(3) . ?
C12 C17 1.383(4) . ?
C12 C13 1.388(4) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.391(4) . ?
C18 C23 1.394(4) . ?
C19 C20 1.378(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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
C1 N1 C2 125.3(2) . . ?
C1 N1 H1 119(2) . . ?
C2 N1 H1 115(2) . . ?
N3 N2 C18 119.9(2) . . ?
N3 N2 C7 112.18(19) . . ?
C18 N2 C7 126.2(2) . . ?
C8 N3 N2 108.7(2) . . ?
O1 C1 N1 123.7(2) . . ?
O1 C1 C6 121.0(2) . . ?
N1 C1 C6 115.2(2) . . ?
N1 C2 C5 110.4(2) . . ?
N1 C2 C4 106.4(2) . . ?
C5 C2 C4 109.6(2) . . ?
N1 C2 C3 110.0(2) . . ?
C5 C2 C3 110.4(2) . . ?
C4 C2 C3 110.0(2) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 C7 112.3(2) . . ?
C1 C6 H6A 110.4(16) . . ?
C7 C6 H6A 108.8(15) . . ?
C1 C6 H6B 108.3(16) . . ?
C7 C6 H6B 109.0(16) . . ?
H6A C6 H6B 108(2) . . ?
N2 C7 C6 110.1(2) . . ?
N2 C7 C11 100.70(19) . . ?
C6 C7 C11 114.0(2) . . ?
N2 C7 H7 109.5(15) . . ?
C6 C7 H7 111.0(15) . . ?
C11 C7 H7 111.0(15) . . ?
N3 C8 C9 120.8(2) . . ?
N3 C8 C11 113.6(2) . . ?
C9 C8 C11 125.5(2) . . ?
O2 C9 C8 119.2(2) . . ?
O2 C9 C10 121.3(2) . . ?
C8 C9 C10 119.5(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 C12 113.0(2) . . ?
C8 C11 C7 100.3(2) . . ?
C12 C11 C7 113.2(2) . . ?
C8 C11 H11 111.6(16) . . ?
C12 C11 H11 107.1(16) . . ?
C7 C11 H11 111.7(16) . . ?
C17 C12 C13 118.4(2) . . ?
C17 C12 C11 122.2(2) . . ?
C13 C12 C11 119.4(2) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.1(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 120.5(3) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C23 119.5(2) . . ?
C19 C18 N2 119.9(2) . . ?
C23 C18 N2 120.6(2) . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 119.5(3) . . ?
C22 C23 H23 120.2 . . ?
C18 C23 H23 120.2 . . ?

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
C18 N2 N3 C8 -176.8(2) . . . . ?
C7 N2 N3 C8 -10.9(3) . . . . ?
C2 N1 C1 O1 -0.4(4) . . . . ?
C2 N1 C1 C6 177.2(2) . . . . ?
C1 N1 C2 C5 62.4(3) . . . . ?
C1 N1 C2 C4 -178.7(2) . . . . ?
C1 N1 C2 C3 -59.6(3) . . . . ?
O1 C1 C6 C7 -28.0(4) . . . . ?
N1 C1 C6 C7 154.3(2) . . . . ?
N3 N2 C7 C6 -100.8(2) . . . . ?
C18 N2 C7 C6 64.0(3) . . . . ?
N3 N2 C7 C11 19.8(2) . . . . ?
C18 N2 C7 C11 -175.4(2) . . . . ?
C1 C6 C7 N2 -174.9(2) . . . . ?
C1 C6 C7 C11 72.8(3) . . . . ?
N2 N3 C8 C9 180.0(2) . . . . ?
N2 N3 C8 C11 -3.9(3) . . . . ?
N3 C8 C9 O2 -173.7(2) . . . . ?
C11 C8 C9 O2 10.7(4) . . . . ?
N3 C8 C9 C10 7.1(4) . . . . ?
C11 C8 C9 C10 -168.5(2) . . . . ?
N3 C8 C11 C12 -105.0(2) . . . . ?
C9 C8 C11 C12 70.9(3) . . . . ?
N3 C8 C11 C7 15.8(3) . . . . ?
C9 C8 C11 C7 -168.4(2) . . . . ?
N2 C7 C11 C8 -19.4(2) . . . . ?
C6 C7 C11 C8 98.4(2) . . . . ?
N2 C7 C11 C12 101.2(2) . . . . ?
C6 C7 C11 C12 -140.9(2) . . . . ?
C8 C11 C12 C17 15.7(3) . . . . ?
C7 C11 C12 C17 -97.4(3) . . . . ?
C8 C11 C12 C13 -166.6(2) . . . . ?
C7 C11 C12 C13 80.2(3) . . . . ?
C17 C12 C13 C14 -0.7(4) . . . . ?
C11 C12 C13 C14 -178.4(2) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 1.1(4) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
C13 C12 C17 C16 0.6(4) . . . . ?
C11 C12 C17 C16 178.3(3) . . . . ?
C15 C16 C17 C12 0.3(5) . . . . ?
N3 N2 C18 C19 -172.5(2) . . . . ?
C7 N2 C18 C19 23.8(3) . . . . ?
N3 N2 C18 C23 5.7(3) . . . . ?
C7 N2 C18 C23 -158.0(2) . . . . ?
C23 C18 C19 C20 -1.2(4) . . . . ?
N2 C18 C19 C20 176.9(2) . . . . ?
C18 C19 C20 C21 0.7(4) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C20 C21 C22 C23 -1.6(4) . . . . ?
C21 C22 C23 C18 1.1(4) . . . . ?
C19 C18 C23 C22 0.3(4) . . . . ?
N2 C18 C23 C22 -177.8(2) . . . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_le113
_database_code_depnum_ccdc_archive 'CCDC 1495183'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-11-18 downloaded from the CCDC.
;
#compound 3f

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H31 N3 O2'
_chemical_formula_sum            'C26 H31 N3 O2'
_chemical_formula_weight         417.54

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'

_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                   9.3834(1)
_cell_length_b                   11.8498(3)
_cell_length_c                   22.2318(5)
_cell_angle_alpha                87.603(1)
_cell_angle_beta                 82.452(1)
_cell_angle_gamma                71.900(1)
_cell_volume                     2329.30(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    9688
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921272
_exptl_absorpt_correction_T_max  1.06396
_exptl_absorpt_process_details   DENZO/SCALEPACK
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.0(1)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31700
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.301
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             10592
_reflns_number_gt                8485
_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       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_solution    SHELXT(Sheldrick,2014)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_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)+(0.0590P)²+1.0615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10592
_refine_ls_number_parameters     581
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.05159(12) 0.41495(12) 0.24447(6) 0.0401(3) Uani 1 1 d . . . . .
O2 O 0.62220(14) 0.21917(11) 0.37416(6) 0.0437(3) Uani 1 1 d . . . . .
N1 N 0.86581(15) 0.39788(13) 0.19396(6) 0.0324(3) Uani 1 1 d . . . . .
H12 H 0.768(2) 0.4111(17) 0.1975(8) 0.039 Uiso 1 1 d . U . . .
N2 N 0.65019(15) 0.58982(12) 0.37650(6) 0.0333(3) Uani 1 1 d . . . . .
N3 N 0.55328(14) 0.52518(12) 0.38819(6) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.91667(16) 0.44371(14) 0.23720(7) 0.0287(3) Uani 1 1 d . . . . .
C2 C 0.96256(17) 0.30852(15) 0.15039(7) 0.0328(3) Uani 1 1 d . . . . .
H11 H 1.0629 0.3227 0.1417 0.039 Uiso 1 1 calc R U . . .
C3 C 0.9874(2) 0.18389(16) 0.17630(8) 0.0431(4) Uani 1 1 d . . . . .
H9 H 0.8884 0.1706 0.1881 0.052 Uiso 1 1 calc R U . . .
H10 H 1.0384 0.1762 0.2132 0.052 Uiso 1 1 calc R U . . .
C4 C 1.0831(3) 0.09008(18) 0.13025(10) 0.0543(5) Uani 1 1 d . . . . .
H7 H 1.1857 0.0981 0.1217 0.065 Uiso 1 1 calc R U . . .
H8 H 1.0927 0.0101 0.1475 0.065 Uiso 1 1 calc R U . . .
C5 C 1.0129(2) 0.10279(19) 0.07138(10) 0.0535(5) Uani 1 1 d . . . . .
H5 H 1.0802 0.0440 0.0415 0.064 Uiso 1 1 calc R U . . .
H6 H 0.9149 0.0863 0.0791 0.064 Uiso 1 1 calc R U . . .
C6 C 0.9883(2) 0.22677(19) 0.04550(9) 0.0499(5) Uani 1 1 d . . . . .
H3 H 0.9368 0.2344 0.0088 0.060 Uiso 1 1 calc R U . . .
H4 H 1.0874 0.2396 0.0334 0.060 Uiso 1 1 calc R U . . .
C7 C 0.8933(2) 0.32170(17) 0.09143(8) 0.0416(4) Uani 1 1 d . . . . .
H1 H 0.8856 0.4013 0.0740 0.050 Uiso 1 1 calc R U . . .
H2 H 0.7900 0.3150 0.0998 0.050 Uiso 1 1 calc R U . . .
C8 C 0.79703(17) 0.53782(14) 0.27633(7) 0.0299(3) Uani 1 1 d . . . . .
H30 H 0.696(2) 0.5403(16) 0.2673(8) 0.036 Uiso 1 1 d . U . . .
H31 H 0.811(2) 0.6187(17) 0.2650(8) 0.036 Uiso 1 1 d . U . . .
C9 C 0.80153(16) 0.51810(13) 0.34538(7) 0.0284(3) Uani 1 1 d . . . . .
C10 C 0.62716(16) 0.41393(13) 0.37797(7) 0.0279(3) Uani 1 1 d . . . . .
C11 C 0.55012(18) 0.32258(14) 0.38521(7) 0.0314(3) Uani 1 1 d . . . . .
C12 C 0.38360(18) 0.35934(16) 0.40673(8) 0.0388(4) Uani 1 1 d . . . . .
H13 H 0.3338 0.3202 0.3820 0.058 Uiso 1 1 calc R U . . .
H14 H 0.3410 0.4456 0.4029 0.058 Uiso 1 1 calc R U . . .
H15 H 0.3674 0.3362 0.4493 0.058 Uiso 1 1 calc R U . . .
C13 C 0.79515(16) 0.39001(13) 0.36238(7) 0.0281(3) Uani 1 1 d . . . . .
H21 H 0.8326 0.3374 0.3259 0.034 Uiso 1 1 calc R U . . .
C14 C 0.88087(17) 0.33354(14) 0.41485(8) 0.0327(3) Uani 1 1 d . U . . .
C15 C 0.8212(2) 0.36394(17) 0.47476(8) 0.0406(4) Uani 1 1 d . U . . .
H20 H 0.7233 0.4196 0.4833 0.049 Uiso 1 1 calc R U . . .
C16 C 0.9024(3) 0.3143(2) 0.52214(10) 0.0557(5) Uani 1 1 d . U . . .
H19 H 0.8605 0.3367 0.5628 0.067 Uiso 1 1 calc R U . . .
C17 C 1.0435(3) 0.2328(2) 0.51066(12) 0.0632(5) Uani 1 1 d . U . . .
H18 H 1.0984 0.1979 0.5432 0.076 Uiso 1 1 calc R U . . .
C18 C 1.1049(2) 0.20181(18) 0.45155(12) 0.0581(5) Uani 1 1 d . U . . .
H17 H 1.2025 0.1456 0.4435 0.070 Uiso 1 1 calc R U . . .
C19 C 1.02428(19) 0.25257(15) 0.40337(10) 0.0440(4) Uani 1 1 d . U . . .
H16 H 1.0678 0.2316 0.3628 0.053 Uiso 1 1 calc R U . . .
C20 C 0.59830(17) 0.71028(13) 0.39417(7) 0.0296(3) Uani 1 1 d . . . . .
C21 C 0.48055(19) 0.74574(16) 0.44135(8) 0.0370(4) Uani 1 1 d . . . . .
H26 H 0.4370 0.6893 0.4609 0.044 Uiso 1 1 calc R U . . .
C22 C 0.4271(2) 0.86305(17) 0.45975(9) 0.0476(5) Uani 1 1 d . . . . .
H25 H 0.3457 0.8870 0.4915 0.057 Uiso 1 1 calc R U . . .
C23 C 0.4910(2) 0.94571(16) 0.43240(9) 0.0442(4) Uani 1 1 d . . . . .
H24 H 0.4546 1.0260 0.4455 0.053 Uiso 1 1 calc R U . . .
C24 C 0.6077(2) 0.91098(15) 0.38611(9) 0.0410(4) Uani 1 1 d . . . . .
H23 H 0.6520 0.9677 0.3674 0.049 Uiso 1 1 calc R U . . .
C25 C 0.6616(2) 0.79390(15) 0.36628(8) 0.0379(4) Uani 1 1 d . . . . .
H22 H 0.7414 0.7710 0.3338 0.046 Uiso 1 1 calc R U . . .
C26 C 0.93216(18) 0.54821(15) 0.36811(8) 0.0334(3) Uani 1 1 d . . . . .
H27 H 0.9366 0.6252 0.3516 0.050 Uiso 1 1 calc R U . . .
H28 H 1.0274 0.4867 0.3548 0.050 Uiso 1 1 calc R U . . .
H29 H 0.9164 0.5520 0.4125 0.050 Uiso 1 1 calc R U . . .
O3 O 0.55557(12) 0.42176(10) 0.22790(6) 0.0408(3) Uani 1 1 d . . . . .
O4 O 0.10023(15) 0.52397(13) 0.06983(6) 0.0487(3) Uani 1 1 d . . . . .
N4 N 0.37143(15) 0.33497(12) 0.24221(6) 0.0310(3) Uani 1 1 d . . . . .
H43 H 0.273(2) 0.3491(16) 0.2472(8) 0.037 Uiso 1 1 d . U . . .
N5 N 0.14859(15) 0.73914(12) 0.22240(6) 0.0339(3) Uani 1 1 d . . . . .
N6 N 0.04697(15) 0.72264(12) 0.18840(6) 0.0326(3) Uani 1 1 d . . . . .
C27 C 0.42097(16) 0.42911(13) 0.24106(7) 0.0285(3) Uani 1 1 d . . . . .
C28 C 0.47007(17) 0.21470(13) 0.22687(7) 0.0308(3) Uani 1 1 d . . . . .
H42 H 0.5700 0.2046 0.2412 0.037 Uiso 1 1 calc R U . . .
C29 C 0.4025(2) 0.12442(15) 0.25965(9) 0.0393(4) Uani 1 1 d . . . . .
H40 H 0.2991 0.1384 0.2491 0.047 Uiso 1 1 calc R U . . .
H41 H 0.3951 0.1350 0.3040 0.047 Uiso 1 1 calc R U . . .
C30 C 0.4986(2) -0.00293(15) 0.24257(9) 0.0437(4) Uani 1 1 d . . . . .
H38 H 0.5976 -0.0202 0.2579 0.052 Uiso 1 1 calc R U . . .
H39 H 0.4475 -0.0589 0.2623 0.052 Uiso 1 1 calc R U . . .
C31 C 0.5236(2) -0.02185(16) 0.17454(9) 0.0442(4) Uani 1 1 d . . . . .
H36 H 0.4259 -0.0134 0.1597 0.053 Uiso 1 1 calc R U . . .
H37 H 0.5913 -0.1033 0.1650 0.053 Uiso 1 1 calc R U . . .
C32 C 0.5938(2) 0.06802(17) 0.14250(9) 0.0489(5) Uani 1 1 d . . . . .
H34 H 0.6047 0.0569 0.0981 0.059 Uiso 1 1 calc R U . . .
H35 H 0.6957 0.0545 0.1545 0.059 Uiso 1 1 calc R U . . .
C33 C 0.4958(2) 0.19487(15) 0.15877(8) 0.0403(4) Uani 1 1 d . . . . .
H32 H 0.5458 0.2514 0.1388 0.048 Uiso 1 1 calc R U . . .
H33 H 0.3971 0.2107 0.1434 0.048 Uiso 1 1 calc R U . . .
C34 C 0.30160(17) 0.54599(14) 0.25862(7) 0.0294(3) Uani 1 1 d . . . . .
H61 H 0.321(2) 0.5699(16) 0.2980(9) 0.035 Uiso 1 1 d . U . . .
H62 H 0.201(2) 0.5350(16) 0.2650(8) 0.035 Uiso 1 1 d . U . . .
C35 C 0.29894(16) 0.64562(13) 0.21097(7) 0.0283(3) Uani 1 1 d . . . . .
C36 C 0.11648(17) 0.64282(14) 0.14768(7) 0.0308(3) Uani 1 1 d . . . . .
C37 C 0.03311(19) 0.60465(16) 0.10523(8) 0.0359(4) Uani 1 1 d . . . . .
C38 C -0.1330(2) 0.66763(19) 0.10675(9) 0.0461(4) Uani 1 1 d . . . . .
H44 H -0.1725 0.6361 0.0747 0.069 Uiso 1 1 calc R U . . .
H45 H -0.1495 0.7528 0.1002 0.069 Uiso 1 1 calc R U . . .
H46 H -0.1856 0.6551 0.1463 0.069 Uiso 1 1 calc R U . . .
C39 C 0.28533(17) 0.60056(14) 0.14718(7) 0.0303(3) Uani 1 1 d . . . . .
H52 H 0.3231 0.5118 0.1460 0.036 Uiso 1 1 calc R U . . .
C40 C 0.36528(18) 0.65066(16) 0.09401(7) 0.0349(4) Uani 1 1 d . . . . .
C41 C 0.3065(2) 0.76782(18) 0.07524(9) 0.0466(4) Uani 1 1 d . . . . .
H51 H 0.2108 0.8155 0.0938 0.056 Uiso 1 1 calc R U . . .
C42 C 0.3865(3) 0.8155(2) 0.02963(10) 0.0627(6) Uani 1 1 d . . . . .
H50 H 0.3463 0.8960 0.0178 0.075 Uiso 1 1 calc R U . . .
C43 C 0.5239(3) 0.7468(3) 0.00157(9) 0.0612(6) Uani 1 1 d . . . . .
H49 H 0.5786 0.7801 -0.0294 0.073 Uiso 1 1 calc R U . . .
C44 C 0.5822(2) 0.6297(2) 0.01831(9) 0.0558(6) Uani 1 1 d . . . . .
H48 H 0.6759 0.5817 -0.0017 0.067 Uiso 1 1 calc R U . . .
C45 C 0.50307(19) 0.58215(18) 0.06478(8) 0.0429(4) Uani 1 1 d . . . . .
H47 H 0.5441 0.5017 0.0766 0.052 Uiso 1 1 calc R U . . .
C46 C 0.09390(18) 0.82617(14) 0.26829(7) 0.0322(3) Uani 1 1 d . . . . .
C47 C -0.03916(19) 0.91787(14) 0.26213(8) 0.0374(4) Uani 1 1 d . . . . .
H57 H -0.0898 0.9207 0.2275 0.045 Uiso 1 1 calc R U . . .
C48 C -0.0974(2) 1.00444(16) 0.30620(9) 0.0448(4) Uani 1 1 d . . . . .
H56 H -0.1878 1.0668 0.3015 0.054 Uiso 1 1 calc R U . . .
C49 C -0.0262(2) 1.00159(17) 0.35684(9) 0.0482(5) Uani 1 1 d . . . . .
H55 H -0.0682 1.0603 0.3875 0.058 Uiso 1 1 calc R U . . .
C50 C 0.1068(2) 0.91254(17) 0.36255(9) 0.0479(5) Uani 1 1 d . . . . .
H54 H 0.1576 0.9115 0.3969 0.058 Uiso 1 1 calc R U . . .
C51 C 0.1678(2) 0.82415(16) 0.31882(8) 0.0411(4) Uani 1 1 d . . . . .
H53 H 0.2592 0.7629 0.3234 0.049 Uiso 1 1 calc R U . . .
C52 C 0.42983(18) 0.69612(14) 0.21078(8) 0.0335(3) Uani 1 1 d . . . . .
H58 H 0.4090 0.7708 0.1879 0.050 Uiso 1 1 calc R U . . .
H59 H 0.5230 0.6392 0.1917 0.050 Uiso 1 1 calc R U . . .
H60 H 0.4417 0.7109 0.2526 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2353(18) . ?
O2 C11 1.2190(19) . ?
N1 C1 1.331(2) . ?
N1 C2 1.463(2) . ?
N1 H12 0.87(2) . ?
N2 N3 1.3547(18) . ?
N2 C20 1.4121(19) . ?
N2 C9 1.5029(18) . ?
N3 C10 1.298(2) . ?
C1 C8 1.519(2) . ?
C2 C7 1.519(2) . ?
C2 C3 1.522(2) . ?
C2 H11 1.0000 . ?
C3 C4 1.524(3) . ?
C3 H9 0.9900 . ?
C3 H10 0.9900 . ?
C4 C5 1.523(3) . ?
C4 H7 0.9900 . ?
C4 H8 0.9900 . ?
C5 C6 1.515(3) . ?
C5 H5 0.9900 . ?
C5 H6 0.9900 . ?
C6 C7 1.528(3) . ?
C6 H3 0.9900 . ?
C6 H4 0.9900 . ?
C7 H1 0.9900 . ?
C7 H2 0.9900 . ?
C8 C9 1.547(2) . ?
C8 H30 0.987(19) . ?
C8 H31 1.022(19) . ?
C9 C26 1.528(2) . ?
C9 C13 1.566(2) . ?
C10 C11 1.470(2) . ?
C10 C13 1.507(2) . ?
C11 C12 1.503(2) . ?
C12 H13 0.9800 . ?
C12 H14 0.9800 . ?
C12 H15 0.9800 . ?
C13 C14 1.517(2) . ?
C13 H21 1.0000 . ?
C14 C19 1.387(2) . ?
C14 C15 1.392(2) . ?
C15 C16 1.385(3) . ?
C15 H20 0.9500 . ?
C16 C17 1.373(3) . ?
C16 H19 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H18 0.9500 . ?
C18 C19 1.399(3) . ?
C18 H17 0.9500 . ?
C19 H16 0.9500 . ?
C20 C25 1.392(2) . ?
C20 C21 1.393(2) . ?
C21 C22 1.383(2) . ?
C21 H26 0.9500 . ?
C22 C23 1.381(3) . ?
C22 H25 0.9500 . ?
C23 C24 1.373(3) . ?
C23 H24 0.9500 . ?
C24 C25 1.390(2) . ?
C24 H23 0.9500 . ?
C25 H22 0.9500 . ?
C26 H27 0.9800 . ?
C26 H28 0.9800 . ?
C26 H29 0.9800 . ?
O3 C27 1.2350(18) . ?
O4 C37 1.220(2) . ?
N4 C27 1.333(2) . ?
N4 C28 1.4636(19) . ?
N4 H43 0.879(19) . ?
N5 N6 1.3553(18) . ?
N5 C46 1.410(2) . ?
N5 C35 1.4970(19) . ?
N6 C36 1.293(2) . ?
C27 C34 1.514(2) . ?
C28 C33 1.518(2) . ?
C28 C29 1.521(2) . ?
C28 H42 1.0000 . ?
C29 C30 1.532(2) . ?
C29 H40 0.9900 . ?
C29 H41 0.9900 . ?
C30 C31 1.515(3) . ?
C30 H38 0.9900 . ?
C30 H39 0.9900 . ?
C31 C32 1.524(3) . ?
C31 H36 0.9900 . ?
C31 H37 0.9900 . ?
C32 C33 1.528(2) . ?
C32 H34 0.9900 . ?
C32 H35 0.9900 . ?
C33 H32 0.9900 . ?
C33 H33 0.9900 . ?
C34 C35 1.549(2) . ?
C34 H61 0.988(19) . ?
C34 H62 0.988(18) . ?
C35 C52 1.524(2) . ?
C35 C39 1.570(2) . ?
C36 C37 1.469(2) . ?
C36 C39 1.505(2) . ?
C37 C38 1.501(2) . ?
C38 H44 0.9800 . ?
C38 H45 0.9800 . ?
C38 H46 0.9800 . ?
C39 C40 1.516(2) . ?
C39 H52 1.0000 . ?
C40 C45 1.387(2) . ?
C40 C41 1.393(3) . ?
C41 C42 1.388(3) . ?
C41 H51 0.9500 . ?
C42 C43 1.375(3) . ?
C42 H50 0.9500 . ?
C43 C44 1.379(3) . ?
C43 H49 0.9500 . ?
C44 C45 1.395(3) . ?
C44 H48 0.9500 . ?
C45 H47 0.9500 . ?
C46 C51 1.391(2) . ?
C46 C47 1.396(2) . ?
C47 C48 1.381(2) . ?
C47 H57 0.9500 . ?
C48 C49 1.377(3) . ?
C48 H56 0.9500 . ?
C49 C50 1.378(3) . ?
C49 H55 0.9500 . ?
C50 C51 1.392(2) . ?
C50 H54 0.9500 . ?
C51 H53 0.9500 . ?
C52 H58 0.9800 . ?
C52 H59 0.9800 . ?
C52 H60 0.9800 . ?

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
C1 N1 C2 123.93(13) . . ?
C1 N1 H12 116.0(12) . . ?
C2 N1 H12 118.6(12) . . ?
N3 N2 C20 117.95(12) . . ?
N3 N2 C9 112.35(12) . . ?
C20 N2 C9 129.71(13) . . ?
C10 N3 N2 108.96(12) . . ?
O1 C1 N1 123.08(14) . . ?
O1 C1 C8 121.74(14) . . ?
N1 C1 C8 115.15(13) . . ?
N1 C2 C7 109.72(13) . . ?
N1 C2 C3 110.97(14) . . ?
C7 C2 C3 111.09(14) . . ?
N1 C2 H11 108.3 . . ?
C7 C2 H11 108.3 . . ?
C3 C2 H11 108.3 . . ?
C2 C3 C4 111.26(16) . . ?
C2 C3 H9 109.4 . . ?
C4 C3 H9 109.4 . . ?
C2 C3 H10 109.4 . . ?
C4 C3 H10 109.4 . . ?
H9 C3 H10 108.0 . . ?
C5 C4 C3 111.18(17) . . ?
C5 C4 H7 109.4 . . ?
C3 C4 H7 109.4 . . ?
C5 C4 H8 109.4 . . ?
C3 C4 H8 109.4 . . ?
H7 C4 H8 108.0 . . ?
C6 C5 C4 110.82(17) . . ?
C6 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
C6 C5 H6 109.5 . . ?
C4 C5 H6 109.5 . . ?
H5 C5 H6 108.1 . . ?
C5 C6 C7 111.68(16) . . ?
C5 C6 H3 109.3 . . ?
C7 C6 H3 109.3 . . ?
C5 C6 H4 109.3 . . ?
C7 C6 H4 109.3 . . ?
H3 C6 H4 107.9 . . ?
C2 C7 C6 111.28(15) . . ?
C2 C7 H1 109.4 . . ?
C6 C7 H1 109.4 . . ?
C2 C7 H2 109.4 . . ?
C6 C7 H2 109.4 . . ?
H1 C7 H2 108.0 . . ?
C1 C8 C9 114.25(13) . . ?
C1 C8 H30 109.4(11) . . ?
C9 C8 H30 108.1(10) . . ?
C1 C8 H31 108.5(10) . . ?
C9 C8 H31 109.0(10) . . ?
H30 C8 H31 107.5(14) . . ?
N2 C9 C26 112.44(13) . . ?
N2 C9 C8 107.08(12) . . ?
C26 C9 C8 113.11(12) . . ?
N2 C9 C13 99.69(11) . . ?
C26 C9 C13 114.13(13) . . ?
C8 C9 C13 109.42(12) . . ?
N3 C10 C11 121.24(13) . . ?
N3 C10 C13 113.54(13) . . ?
C11 C10 C13 125.11(13) . . ?
O2 C11 C10 119.64(14) . . ?
O2 C11 C12 121.53(15) . . ?
C10 C11 C12 118.83(14) . . ?
C11 C12 H13 109.5 . . ?
C11 C12 H14 109.5 . . ?
H13 C12 H14 109.5 . . ?
C11 C12 H15 109.5 . . ?
H13 C12 H15 109.5 . . ?
H14 C12 H15 109.5 . . ?
C10 C13 C14 111.97(13) . . ?
C10 C13 C9 100.61(11) . . ?
C14 C13 C9 114.55(12) . . ?
C10 C13 H21 109.8 . . ?
C14 C13 H21 109.8 . . ?
C9 C13 H21 109.8 . . ?
C19 C14 C15 118.61(17) . . ?
C19 C14 C13 119.83(16) . . ?
C15 C14 C13 121.53(14) . . ?
C16 C15 C14 120.96(18) . . ?
C16 C15 H20 119.5 . . ?
C14 C15 H20 119.5 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H19 119.9 . . ?
C15 C16 H19 119.9 . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 H18 120.2 . . ?
C18 C17 H18 120.2 . . ?
C17 C18 C19 120.43(19) . . ?
C17 C18 H17 119.8 . . ?
C19 C18 H17 119.8 . . ?
C14 C19 C18 120.1(2) . . ?
C14 C19 H16 120.0 . . ?
C18 C19 H16 120.0 . . ?
C25 C20 C21 119.29(15) . . ?
C25 C20 N2 122.10(14) . . ?
C21 C20 N2 118.60(14) . . ?
C22 C21 C20 120.03(17) . . ?
C22 C21 H26 120.0 . . ?
C20 C21 H26 120.0 . . ?
C23 C22 C21 120.60(17) . . ?
C23 C22 H25 119.7 . . ?
C21 C22 H25 119.7 . . ?
C24 C23 C22 119.54(16) . . ?
C24 C23 H24 120.2 . . ?
C22 C23 H24 120.2 . . ?
C23 C24 C25 120.81(17) . . ?
C23 C24 H23 119.6 . . ?
C25 C24 H23 119.6 . . ?
C24 C25 C20 119.71(16) . . ?
C24 C25 H22 120.1 . . ?
C20 C25 H22 120.1 . . ?
C9 C26 H27 109.5 . . ?
C9 C26 H28 109.5 . . ?
H27 C26 H28 109.5 . . ?
C9 C26 H29 109.5 . . ?
H27 C26 H29 109.5 . . ?
H28 C26 H29 109.5 . . ?
C27 N4 C28 123.40(13) . . ?
C27 N4 H43 116.7(12) . . ?
C28 N4 H43 119.2(12) . . ?
N6 N5 C46 117.27(13) . . ?
N6 N5 C35 112.14(12) . . ?
C46 N5 C35 129.74(13) . . ?
C36 N6 N5 109.11(13) . . ?
O3 C27 N4 122.59(14) . . ?
O3 C27 C34 121.84(14) . . ?
N4 C27 C34 115.55(13) . . ?
N4 C28 C33 111.08(13) . . ?
N4 C28 C29 109.72(13) . . ?
C33 C28 C29 111.06(14) . . ?
N4 C28 H42 108.3 . . ?
C33 C28 H42 108.3 . . ?
C29 C28 H42 108.3 . . ?
C28 C29 C30 111.45(14) . . ?
C28 C29 H40 109.3 . . ?
C30 C29 H40 109.3 . . ?
C28 C29 H41 109.3 . . ?
C30 C29 H41 109.3 . . ?
H40 C29 H41 108.0 . . ?
C31 C30 C29 111.75(15) . . ?
C31 C30 H38 109.3 . . ?
C29 C30 H38 109.3 . . ?
C31 C30 H39 109.3 . . ?
C29 C30 H39 109.3 . . ?
H38 C30 H39 107.9 . . ?
C30 C31 C32 110.59(15) . . ?
C30 C31 H36 109.5 . . ?
C32 C31 H36 109.5 . . ?
C30 C31 H37 109.5 . . ?
C32 C31 H37 109.5 . . ?
H36 C31 H37 108.1 . . ?
C31 C32 C33 110.89(16) . . ?
C31 C32 H34 109.5 . . ?
C33 C32 H34 109.5 . . ?
C31 C32 H35 109.5 . . ?
C33 C32 H35 109.5 . . ?
H34 C32 H35 108.1 . . ?
C28 C33 C32 111.43(15) . . ?
C28 C33 H32 109.3 . . ?
C32 C33 H32 109.3 . . ?
C28 C33 H33 109.3 . . ?
C32 C33 H33 109.3 . . ?
H32 C33 H33 108.0 . . ?
C27 C34 C35 113.64(13) . . ?
C27 C34 H61 107.3(10) . . ?
C35 C34 H61 110.2(11) . . ?
C27 C34 H62 110.0(11) . . ?
C35 C34 H62 108.4(11) . . ?
H61 C34 H62 107.2(15) . . ?
N5 C35 C52 112.20(13) . . ?
N5 C35 C34 107.75(12) . . ?
C52 C35 C34 113.15(12) . . ?
N5 C35 C39 99.68(11) . . ?
C52 C35 C39 113.71(13) . . ?
C34 C35 C39 109.41(12) . . ?
N6 C36 C37 120.95(14) . . ?
N6 C36 C39 113.63(13) . . ?
C37 C36 C39 125.36(14) . . ?
O4 C37 C36 119.48(15) . . ?
O4 C37 C38 122.16(15) . . ?
C36 C37 C38 118.36(15) . . ?
C37 C38 H44 109.5 . . ?
C37 C38 H45 109.5 . . ?
H44 C38 H45 109.5 . . ?
C37 C38 H46 109.5 . . ?
H44 C38 H46 109.5 . . ?
H45 C38 H46 109.5 . . ?
C36 C39 C40 112.08(13) . . ?
C36 C39 C35 100.41(12) . . ?
C40 C39 C35 114.49(13) . . ?
C36 C39 H52 109.8 . . ?
C40 C39 H52 109.8 . . ?
C35 C39 H52 109.8 . . ?
C45 C40 C41 118.41(17) . . ?
C45 C40 C39 120.41(16) . . ?
C41 C40 C39 121.10(15) . . ?
C42 C41 C40 120.58(19) . . ?
C42 C41 H51 119.7 . . ?
C40 C41 H51 119.7 . . ?
C43 C42 C41 120.3(2) . . ?
C43 C42 H50 119.9 . . ?
C41 C42 H50 119.9 . . ?
C42 C43 C44 120.1(2) . . ?
C42 C43 H49 120.0 . . ?
C44 C43 H49 120.0 . . ?
C43 C44 C45 119.72(19) . . ?
C43 C44 H48 120.1 . . ?
C45 C44 H48 120.1 . . ?
C40 C45 C44 120.9(2) . . ?
C40 C45 H47 119.6 . . ?
C44 C45 H47 119.6 . . ?
C51 C46 C47 119.23(15) . . ?
C51 C46 N5 122.55(14) . . ?
C47 C46 N5 118.21(15) . . ?
C48 C47 C46 120.17(17) . . ?
C48 C47 H57 119.9 . . ?
C46 C47 H57 119.9 . . ?
C49 C48 C47 120.82(17) . . ?
C49 C48 H56 119.6 . . ?
C47 C48 H56 119.6 . . ?
C48 C49 C50 119.21(17) . . ?
C48 C49 H55 120.4 . . ?
C50 C49 H55 120.4 . . ?
C49 C50 C51 121.11(18) . . ?
C49 C50 H54 119.4 . . ?
C51 C50 H54 119.4 . . ?
C46 C51 C50 119.44(17) . . ?
C46 C51 H53 120.3 . . ?
C50 C51 H53 120.3 . . ?
C35 C52 H58 109.5 . . ?
C35 C52 H59 109.5 . . ?
H58 C52 H59 109.5 . . ?
C35 C52 H60 109.5 . . ?
H58 C52 H60 109.5 . . ?
H59 C52 H60 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C20 N2 N3 C10 -169.78(14) . . . . ?
C9 N2 N3 C10 10.34(18) . . . . ?
C2 N1 C1 O1 0.2(3) . . . . ?
C2 N1 C1 C8 178.35(14) . . . . ?
C1 N1 C2 C7 -150.78(16) . . . . ?
C1 N1 C2 C3 86.07(19) . . . . ?
N1 C2 C3 C4 177.83(15) . . . . ?
C7 C2 C3 C4 55.5(2) . . . . ?
C2 C3 C4 C5 -56.0(2) . . . . ?
C3 C4 C5 C6 55.8(2) . . . . ?
C4 C5 C6 C7 -55.4(2) . . . . ?
N1 C2 C7 C6 -177.88(15) . . . . ?
C3 C2 C7 C6 -54.8(2) . . . . ?
C5 C6 C7 C2 55.2(2) . . . . ?
O1 C1 C8 C9 -51.1(2) . . . . ?
N1 C1 C8 C9 130.73(15) . . . . ?
N3 N2 C9 C26 -141.22(14) . . . . ?
C20 N2 C9 C26 38.9(2) . . . . ?
N3 N2 C9 C8 93.96(15) . . . . ?
C20 N2 C9 C8 -85.90(19) . . . . ?
N3 N2 C9 C13 -19.95(16) . . . . ?
C20 N2 C9 C13 160.19(16) . . . . ?
C1 C8 C9 N2 -160.79(12) . . . . ?
C1 C8 C9 C26 74.80(17) . . . . ?
C1 C8 C9 C13 -53.64(16) . . . . ?
N2 N3 C10 C11 -178.28(14) . . . . ?
N2 N3 C10 C13 5.23(18) . . . . ?
N3 C10 C11 O2 178.62(16) . . . . ?
C13 C10 C11 O2 -5.3(2) . . . . ?
N3 C10 C11 C12 -1.9(2) . . . . ?
C13 C10 C11 C12 174.15(15) . . . . ?
N3 C10 C13 C14 104.91(16) . . . . ?
C11 C10 C13 C14 -71.42(19) . . . . ?
N3 C10 C13 C9 -17.19(17) . . . . ?
C11 C10 C13 C9 166.48(14) . . . . ?
N2 C9 C13 C10 20.14(14) . . . . ?
C26 C9 C13 C10 140.18(13) . . . . ?
C8 C9 C13 C10 -91.95(13) . . . . ?
N2 C9 C13 C14 -100.13(14) . . . . ?
C26 C9 C13 C14 19.92(18) . . . . ?
C8 C9 C13 C14 147.78(13) . . . . ?
C10 C13 C14 C19 146.75(15) . . . . ?
C9 C13 C14 C19 -99.51(17) . . . . ?
C10 C13 C14 C15 -35.5(2) . . . . ?
C9 C13 C14 C15 78.28(18) . . . . ?
C19 C14 C15 C16 -0.3(3) . . . . ?
C13 C14 C15 C16 -178.13(17) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C15 C14 C19 C18 1.0(3) . . . . ?
C13 C14 C19 C18 178.89(16) . . . . ?
C17 C18 C19 C14 -0.8(3) . . . . ?
N3 N2 C20 C25 -155.83(15) . . . . ?
C9 N2 C20 C25 24.0(3) . . . . ?
N3 N2 C20 C21 24.6(2) . . . . ?
C9 N2 C20 C21 -155.55(16) . . . . ?
C25 C20 C21 C22 0.4(3) . . . . ?
N2 C20 C21 C22 180.00(16) . . . . ?
C20 C21 C22 C23 -1.0(3) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 C20 -0.9(3) . . . . ?
C21 C20 C25 C24 0.5(3) . . . . ?
N2 C20 C25 C24 -179.02(16) . . . . ?
C46 N5 N6 C36 178.12(14) . . . . ?
C35 N5 N6 C36 -11.41(19) . . . . ?
C28 N4 C27 O3 -1.3(2) . . . . ?
C28 N4 C27 C34 -179.81(14) . . . . ?
C27 N4 C28 C33 -83.61(19) . . . . ?
C27 N4 C28 C29 153.22(15) . . . . ?
N4 C28 C29 C30 177.37(14) . . . . ?
C33 C28 C29 C30 54.19(19) . . . . ?
C28 C29 C30 C31 -54.8(2) . . . . ?
C29 C30 C31 C32 55.6(2) . . . . ?
C30 C31 C32 C33 -56.4(2) . . . . ?
N4 C28 C33 C32 -177.82(14) . . . . ?
C29 C28 C33 C32 -55.42(19) . . . . ?
C31 C32 C33 C28 56.6(2) . . . . ?
O3 C27 C34 C35 54.8(2) . . . . ?
N4 C27 C34 C35 -126.75(15) . . . . ?
N6 N5 C35 C52 141.36(14) . . . . ?
C46 N5 C35 C52 -49.7(2) . . . . ?
N6 N5 C35 C34 -93.44(15) . . . . ?
C46 N5 C35 C34 75.5(2) . . . . ?
N6 N5 C35 C39 20.68(16) . . . . ?
C46 N5 C35 C39 -170.35(16) . . . . ?
C27 C34 C35 N5 160.84(12) . . . . ?
C27 C34 C35 C52 -74.52(17) . . . . ?
C27 C34 C35 C39 53.39(16) . . . . ?
N5 N6 C36 C37 178.38(14) . . . . ?
N5 N6 C36 C39 -4.37(19) . . . . ?
N6 C36 C37 O4 -175.42(16) . . . . ?
C39 C36 C37 O4 7.7(3) . . . . ?
N6 C36 C37 C38 5.0(2) . . . . ?
C39 C36 C37 C38 -171.90(16) . . . . ?
N6 C36 C39 C40 -105.19(16) . . . . ?
C37 C36 C39 C40 71.9(2) . . . . ?
N6 C36 C39 C35 16.78(18) . . . . ?
C37 C36 C39 C35 -166.11(15) . . . . ?
N5 C35 C39 C36 -20.37(14) . . . . ?
C52 C35 C39 C36 -139.95(13) . . . . ?
C34 C35 C39 C36 92.46(13) . . . . ?
N5 C35 C39 C40 99.87(14) . . . . ?
C52 C35 C39 C40 -19.70(18) . . . . ?
C34 C35 C39 C40 -147.30(13) . . . . ?
C36 C39 C40 C45 -143.53(15) . . . . ?
C35 C39 C40 C45 102.95(17) . . . . ?
C36 C39 C40 C41 39.7(2) . . . . ?
C35 C39 C40 C41 -73.83(19) . . . . ?
C45 C40 C41 C42 -1.9(3) . . . . ?
C39 C40 C41 C42 174.90(19) . . . . ?
C40 C41 C42 C43 1.2(3) . . . . ?
C41 C42 C43 C44 0.5(4) . . . . ?
C42 C43 C44 C45 -1.5(3) . . . . ?
C41 C40 C45 C44 0.9(3) . . . . ?
C39 C40 C45 C44 -175.92(16) . . . . ?
C43 C44 C45 C40 0.8(3) . . . . ?
N6 N5 C46 C51 156.37(16) . . . . ?
C35 N5 C46 C51 -12.1(3) . . . . ?
N6 N5 C46 C47 -24.0(2) . . . . ?
C35 N5 C46 C47 167.48(16) . . . . ?
C51 C46 C47 C48 -0.9(3) . . . . ?
N5 C46 C47 C48 179.49(16) . . . . ?
C46 C47 C48 C49 -0.3(3) . . . . ?
C47 C48 C49 C50 1.6(3) . . . . ?
C48 C49 C50 C51 -1.6(3) . . . . ?
C47 C46 C51 C50 0.8(3) . . . . ?
N5 C46 C51 C50 -179.55(17) . . . . ?
C49 C50 C51 C46 0.4(3) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.220
_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_le198
_database_code_depnum_ccdc_archive 'CCDC 1495184'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-11-18 downloaded from the CCDC.
;
#compound 5g

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H27 N4 O5 P'
_chemical_formula_sum            'C25 H27 N4 O5 P'
_chemical_formula_weight         494.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   29.5009(5)
_cell_length_b                   7.6614(2)
_cell_length_c                   21.6674(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.924(1)
_cell_angle_gamma                90
_cell_volume                     4890.85(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    9998
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             2080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953134
_exptl_absorpt_correction_T_max  1.07681
_exptl_absorpt_process_details   DENZO/SCALEPACK
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.0(1)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34439
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.747
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5582
_reflns_number_gt                4270
_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       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_solution    SHELXT(Sheldrick,2014)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_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)+(0.1051P)²+10.2772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5582
_refine_ls_number_parameters     374
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.2136
_refine_ls_wR_factor_gt          0.1934
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.07424(3) 0.06872(13) 0.22996(3) 0.0466(3) Uani 1 1 d D . . . .
O1 O -0.06434(8) 0.2456(4) 0.59072(11) 0.0676(8) Uani 1 1 d . . . . .
O2 O -0.10129(7) 0.3030(4) 0.50469(12) 0.0673(8) Uani 1 1 d . . . . .
N1 N 0.09516(7) 0.2230(3) 0.41014(9) 0.0337(5) Uani 1 1 d . . . . .
N2 N 0.13454(7) 0.1709(3) 0.44133(9) 0.0319(5) Uani 1 1 d . . . . .
N3 N -0.06568(9) 0.2701(4) 0.53472(12) 0.0481(6) Uani 1 1 d . . . . .
N4 N 0.24478(7) 0.1310(3) 0.38263(11) 0.0381(5) Uani 1 1 d . . . . .
C2 C -0.02389(9) 0.2600(4) 0.50264(13) 0.0359(6) Uani 1 1 d . . . . .
C3 C -0.02423(9) 0.2988(4) 0.44050(13) 0.0384(6) Uani 1 1 d . . . . .
H3 H -0.0517 0.3338 0.4192 0.046 Uiso 1 1 calc R U . . .
C4 C 0.01527(9) 0.2869(4) 0.40923(12) 0.0371(6) Uani 1 1 d . . . . .
H4 H 0.0151 0.3139 0.3664 0.044 Uiso 1 1 calc R U . . .
C5 C 0.05551(8) 0.2348(4) 0.44087(11) 0.0308(5) Uani 1 1 d . . . . .
C6 C 0.05514(9) 0.1958(4) 0.50447(11) 0.0345(6) Uani 1 1 d . . . . .
H6 H 0.0824 0.1606 0.5263 0.041 Uiso 1 1 calc R U . . .
C7 C 0.01566(9) 0.2083(4) 0.53493(12) 0.0373(6) Uani 1 1 d . . . . .
H7 H 0.0154 0.1818 0.5777 0.045 Uiso 1 1 calc R U . . .
C8 C 0.16684(8) 0.1732(3) 0.40325(11) 0.0289(5) Uani 1 1 d . . . . .
C9 C 0.15212(8) 0.2366(3) 0.33903(11) 0.0285(5) Uani 1 1 d . . . . .
H9 H 0.1620(10) 0.159(4) 0.3070(13) 0.034 Uiso 1 1 d . U . . .
C10 C 0.09990(8) 0.2271(4) 0.34220(11) 0.0305(5) Uani 1 1 d . . . . .
H10 H 0.0833(10) 0.336(4) 0.3237(13) 0.037 Uiso 1 1 d . U . . .
C11 C 0.07888(9) 0.0614(4) 0.31249(12) 0.0359(6) Uani 1 1 d . . . . .
H11A H 0.0467(11) 0.049(4) 0.3244(14) 0.043 Uiso 1 1 d . U . . .
H11B H 0.0985(11) -0.052(4) 0.3267(14) 0.043 Uiso 1 1 d . U . . .
C12 C 0.16941(8) 0.4197(3) 0.32728(11) 0.0289(5) Uani 1 1 d . . . . .
C13 C 0.15906(9) 0.5562(4) 0.36645(12) 0.0332(6) Uani 1 1 d . . . . .
H13 H 0.1412 0.5341 0.4009 0.040 Uiso 1 1 calc R U . . .
C14 C 0.17434(9) 0.7237(4) 0.35599(13) 0.0386(6) Uani 1 1 d . . . . .
H14 H 0.1670 0.8156 0.3832 0.046 Uiso 1 1 calc R U . . .
C15 C 0.20048(9) 0.7579(4) 0.30575(14) 0.0399(6) Uani 1 1 d . . . . .
H15 H 0.2114 0.8725 0.2988 0.048 Uiso 1 1 calc R U . . .
C16 C 0.21040(10) 0.6241(4) 0.26620(13) 0.0412(7) Uani 1 1 d . . . . .
H16 H 0.2277 0.6473 0.2313 0.049 Uiso 1 1 calc R U . . .
C17 C 0.19541(9) 0.4564(4) 0.27689(12) 0.0363(6) Uani 1 1 d . . . . .
H17 H 0.2029 0.3650 0.2496 0.044 Uiso 1 1 calc R U . . .
C18 C 0.21260(8) 0.1161(3) 0.42367(12) 0.0308(5) Uani 1 1 d . . . . .
C19 C 0.22103(10) 0.0476(4) 0.48278(14) 0.0423(7) Uani 1 1 d . . . . .
H19 H 0.1973 0.0388 0.5107 0.051 Uiso 1 1 calc R U . . .
C20 C 0.26449(11) -0.0071(5) 0.50017(15) 0.0507(8) Uani 1 1 d . . . . .
H20 H 0.2711 -0.0547 0.5401 0.061 Uiso 1 1 calc R U . . .
C21 C 0.29776(10) 0.0087(5) 0.45875(16) 0.0494(8) Uani 1 1 d . . . . .
H21 H 0.3280 -0.0270 0.4695 0.059 Uiso 1 1 calc R U . . .
C22 C 0.28664(10) 0.0772(5) 0.40131(15) 0.0471(7) Uani 1 1 d . . . . .
H22 H 0.3100 0.0871 0.3730 0.056 Uiso 1 1 calc R U . . .
O4 O 0.12432(7) 0.0507(4) 0.21113(9) 0.0579(7) Uani 1 1 d . . . . .
O3 O 0.0579(2) 0.2479(8) 0.2041(3) 0.0627(15) Uani 0.61 1 d . . P A 1
O5 O 0.0544(2) -0.1216(9) 0.2100(3) 0.0600(18) Uani 0.61 1 d D . P A 1
C24 C 0.1814(2) 0.0842(8) 0.1390(2) 0.0985(18) Uani 0.61 1 d . . P B 1
H24A H 0.2005 0.1458 0.1702 0.148 Uiso 0.61 1 calc R U P B 1
H24B H 0.1890 0.1232 0.0977 0.148 Uiso 0.61 1 calc R U P B 1
H24C H 0.1867 -0.0418 0.1427 0.148 Uiso 0.61 1 calc R U P B 1
C23 C 0.1346(3) 0.1210(11) 0.1482(4) 0.0548(19) Uani 0.61 1 d . . P B 1
H23A H 0.1150 0.0639 0.1157 0.066 Uiso 0.61 1 calc R U P B 1
H23B H 0.1291 0.2484 0.1463 0.066 Uiso 0.61 1 calc R U P B 1
C25 C 0.0797(3) -0.2984(10) 0.2193(4) 0.075(2) Uani 0.61 1 d . . P A 1
H25A H 0.1067 -0.2802 0.2477 0.090 Uiso 0.61 1 calc R U P A 1
H25B H 0.0594 -0.3817 0.2393 0.090 Uiso 0.61 1 calc R U P A 1
C26 C 0.0924(4) -0.3654(13) 0.1695(6) 0.121(3) Uani 0.61 1 d D . P A 1
H26A H 0.0672 -0.3618 0.1382 0.182 Uiso 0.61 1 calc R U P A 1
H26B H 0.1015 -0.4868 0.1770 0.182 Uiso 0.61 1 calc R U P A 1
H26C H 0.1181 -0.2992 0.1549 0.182 Uiso 0.61 1 calc R U P A 1
O3A O 0.0422(2) 0.1855(10) 0.2061(4) 0.0417(16) Uani 0.39 1 d . . P A 2
O5A O 0.0411(3) -0.0662(14) 0.2025(5) 0.051(2) Uani 0.39 1 d D . P A 2
C23A C 0.1357(6) 0.024(2) 0.1477(7) 0.082(5) Uani 0.39 1 d . . P B 2
H23C H 0.1333 -0.1013 0.1372 0.098 Uiso 0.39 1 calc R U P B 2
H23D H 0.1141 0.0892 0.1198 0.098 Uiso 0.39 1 calc R U P B 2
C24A C 0.1814(2) 0.0842(8) 0.1390(2) 0.0985(18) Uani 0.39 1 d . . P B 2
H24D H 0.1814 0.2115 0.1347 0.148 Uiso 0.39 1 calc R U P B 2
H24E H 0.1926 0.0312 0.1015 0.148 Uiso 0.39 1 calc R U P B 2
H24F H 0.2011 0.0504 0.1747 0.148 Uiso 0.39 1 calc R U P B 2
C25A C 0.0467(4) -0.2449(15) 0.2265(6) 0.073(4) Uani 0.39 1 d . . P A 2
H25C H 0.0796 -0.2599 0.2369 0.088 Uiso 0.39 1 calc R U P A 2
H25D H 0.0316 -0.2475 0.2663 0.088 Uiso 0.39 1 calc R U P A 2
C26A C 0.0341(6) -0.3803(17) 0.1978(8) 0.121(3) Uani 0.39 1 d D . P A 2
H26D H 0.0131 -0.3484 0.1632 0.182 Uiso 0.39 1 calc R U P A 2
H26E H 0.0188 -0.4586 0.2258 0.182 Uiso 0.39 1 calc R U P A 2
H26F H 0.0606 -0.4396 0.1821 0.182 Uiso 0.39 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3A 1.384(8) . ?
P1 O5A 1.522(9) . ?
P1 O3 1.550(6) . ?
P1 O4 1.559(2) . ?
P1 O5 1.621(7) . ?
P1 C11 1.788(3) . ?
O1 N3 1.226(3) . ?
O2 N3 1.233(3) . ?
N1 N2 1.373(3) . ?
N1 C5 1.378(3) . ?
N1 C10 1.486(3) . ?
N2 C8 1.292(3) . ?
N3 C2 1.448(3) . ?
N4 C18 1.338(3) . ?
N4 C22 1.345(4) . ?
C2 C3 1.379(4) . ?
C2 C7 1.387(4) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.411(3) . ?
C6 C7 1.371(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C18 1.466(3) . ?
C8 C9 1.516(3) . ?
C9 C12 1.518(4) . ?
C9 C10 1.547(3) . ?
C9 H9 0.97(3) . ?
C10 C11 1.540(4) . ?
C10 H10 1.03(3) . ?
C11 H11A 1.00(3) . ?
C11 H11B 1.08(3) . ?
C12 C13 1.391(4) . ?
C12 C17 1.395(4) . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.394(4) . ?
C19 C20 1.383(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.369(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
O4 C23A 1.446(14) . ?
O4 C23 1.512(8) . ?
O5 C25 1.554(9) . ?
C24 C23 1.432(11) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C25 C26 1.268(13) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O5A C25A 1.471(17) . ?
C23A C24A 1.445(17) . ?
C23A H23C 0.9900 . ?
C23A H23D 0.9900 . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
C25A C26A 1.256(16) . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?
C26A H26D 0.9800 . ?
C26A H26E 0.9800 . ?
C26A H26F 0.9800 . ?

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
O3A P1 O5A 83.1(4) . . ?
O3A P1 O4 126.8(3) . . ?
O5A P1 O4 115.8(4) . . ?
O3 P1 O4 105.4(2) . . ?
O3 P1 O5 126.8(3) . . ?
O4 P1 O5 100.6(3) . . ?
O3A P1 C11 114.2(3) . . ?
O5A P1 C11 112.6(5) . . ?
O3 P1 C11 113.3(3) . . ?
O4 P1 C11 103.52(12) . . ?
O5 P1 C11 104.3(3) . . ?
N2 N1 C5 119.9(2) . . ?
N2 N1 C10 111.93(19) . . ?
C5 N1 C10 127.0(2) . . ?
C8 N2 N1 108.3(2) . . ?
O1 N3 O2 122.5(3) . . ?
O1 N3 C2 118.8(3) . . ?
O2 N3 C2 118.7(3) . . ?
C18 N4 C22 116.5(3) . . ?
C3 C2 C7 121.2(2) . . ?
C3 C2 N3 119.6(2) . . ?
C7 C2 N3 119.2(2) . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 120.1(2) . . ?
N1 C5 C6 120.5(2) . . ?
C4 C5 C6 119.4(2) . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 119.4(2) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
N2 C8 C18 120.1(2) . . ?
N2 C8 C9 113.8(2) . . ?
C18 C8 C9 126.1(2) . . ?
C8 C9 C12 111.6(2) . . ?
C8 C9 C10 100.56(19) . . ?
C12 C9 C10 113.2(2) . . ?
C8 C9 H9 112.3(17) . . ?
C12 C9 H9 109.1(18) . . ?
C10 C9 H9 109.9(17) . . ?
N1 C10 C11 109.9(2) . . ?
N1 C10 C9 100.91(18) . . ?
C11 C10 C9 113.6(2) . . ?
N1 C10 H10 109.5(16) . . ?
C11 C10 H10 109.1(17) . . ?
C9 C10 H10 113.4(16) . . ?
C10 C11 P1 113.64(19) . . ?
C10 C11 H11A 109.8(18) . . ?
P1 C11 H11A 103.7(18) . . ?
C10 C11 H11B 110.1(17) . . ?
P1 C11 H11B 108.9(17) . . ?
H11A C11 H11B 111(2) . . ?
C13 C12 C17 118.2(2) . . ?
C13 C12 C9 120.4(2) . . ?
C17 C12 C9 121.4(2) . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
N4 C18 C19 122.9(2) . . ?
N4 C18 C8 116.6(2) . . ?
C19 C18 C8 120.5(2) . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 118.7(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 118.8(3) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
N4 C22 C21 124.2(3) . . ?
N4 C22 H22 117.9 . . ?
C21 C22 H22 117.9 . . ?
C23A O4 P1 122.1(7) . . ?
C23 O4 P1 116.2(4) . . ?
C25 O5 P1 125.9(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C24 C23 O4 107.1(6) . . ?
C24 C23 H23A 110.3 . . ?
O4 C23 H23A 110.3 . . ?
C24 C23 H23B 110.3 . . ?
O4 C23 H23B 110.3 . . ?
H23A C23 H23B 108.5 . . ?
C26 C25 O5 113.8(7) . . ?
C26 C25 H25A 108.8 . . ?
O5 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
O5 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25A O5A P1 115.9(7) . . ?
C24A C23A O4 110.1(10) . . ?
C24A C23A H23C 109.6 . . ?
O4 C23A H23C 109.6 . . ?
C24A C23A H23D 109.6 . . ?
O4 C23A H23D 109.6 . . ?
H23C C23A H23D 108.2 . . ?
C23A C24A H24D 109.5 . . ?
C23A C24A H24E 109.5 . . ?
H24D C24A H24E 109.5 . . ?
C23A C24A H24F 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
C26A C25A O5A 124.7(13) . . ?
C26A C25A H25C 106.2 . . ?
O5A C25A H25C 106.2 . . ?
C26A C25A H25D 106.2 . . ?
O5A C25A H25D 106.2 . . ?
H25C C25A H25D 106.4 . . ?
C25A C26A H26D 109.5 . . ?
C25A C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
C25A C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C8 -178.9(2) . . . . ?
C10 N1 N2 C8 12.3(3) . . . . ?
O1 N3 C2 C3 -175.6(3) . . . . ?
O2 N3 C2 C3 4.4(5) . . . . ?
O1 N3 C2 C7 5.5(5) . . . . ?
O2 N3 C2 C7 -174.5(3) . . . . ?
C7 C2 C3 C4 -0.1(5) . . . . ?
N3 C2 C3 C4 -179.0(3) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
N2 N1 C5 C4 -179.6(3) . . . . ?
C10 N1 C5 C4 -12.6(4) . . . . ?
N2 N1 C5 C6 0.8(4) . . . . ?
C10 N1 C5 C6 167.8(3) . . . . ?
C3 C4 C5 N1 -179.8(3) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
N1 C5 C6 C7 179.8(3) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C5 C6 C7 C2 -0.1(4) . . . . ?
C3 C2 C7 C6 0.1(5) . . . . ?
N3 C2 C7 C6 178.9(3) . . . . ?
N1 N2 C8 C18 -177.5(2) . . . . ?
N1 N2 C8 C9 2.1(3) . . . . ?
N2 C8 C9 C12 106.1(2) . . . . ?
C18 C8 C9 C12 -74.4(3) . . . . ?
N2 C8 C9 C10 -14.2(3) . . . . ?
C18 C8 C9 C10 165.2(2) . . . . ?
N2 N1 C10 C11 100.0(2) . . . . ?
C5 N1 C10 C11 -67.9(3) . . . . ?
N2 N1 C10 C9 -20.3(3) . . . . ?
C5 N1 C10 C9 171.9(3) . . . . ?
C8 C9 C10 N1 18.9(2) . . . . ?
C12 C9 C10 N1 -100.2(2) . . . . ?
C8 C9 C10 C11 -98.7(2) . . . . ?
C12 C9 C10 C11 142.2(2) . . . . ?
N1 C10 C11 P1 170.24(17) . . . . ?
C9 C10 C11 P1 -77.5(2) . . . . ?
O3A P1 C11 C10 -69.8(4) . . . . ?
O5A P1 C11 C10 -162.4(4) . . . . ?
O3 P1 C11 C10 -41.9(3) . . . . ?
O4 P1 C11 C10 71.8(2) . . . . ?
O5 P1 C11 C10 176.7(3) . . . . ?
C8 C9 C12 C13 -56.4(3) . . . . ?
C10 C9 C12 C13 56.1(3) . . . . ?
C8 C9 C12 C17 124.4(3) . . . . ?
C10 C9 C12 C17 -123.0(2) . . . . ?
C17 C12 C13 C14 -0.4(4) . . . . ?
C9 C12 C13 C14 -179.6(2) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C15 C16 C17 C12 1.0(4) . . . . ?
C13 C12 C17 C16 -0.1(4) . . . . ?
C9 C12 C17 C16 179.1(2) . . . . ?
C22 N4 C18 C19 -0.4(4) . . . . ?
C22 N4 C18 C8 -179.5(3) . . . . ?
N2 C8 C18 N4 -176.5(2) . . . . ?
C9 C8 C18 N4 4.1(4) . . . . ?
N2 C8 C18 C19 4.5(4) . . . . ?
C9 C8 C18 C19 -175.0(3) . . . . ?
N4 C18 C19 C20 0.2(5) . . . . ?
C8 C18 C19 C20 179.1(3) . . . . ?
C18 C19 C20 C21 0.3(5) . . . . ?
C19 C20 C21 C22 -0.4(5) . . . . ?
C18 N4 C22 C21 0.3(5) . . . . ?
C20 C21 C22 N4 0.2(5) . . . . ?
O3A P1 O4 C23A -54.4(10) . . . . ?
O5A P1 O4 C23A 46.9(10) . . . . ?
C11 P1 O4 C23A 170.6(9) . . . . ?
O3 P1 O4 C23 -37.6(4) . . . . ?
O5 P1 O4 C23 95.5(5) . . . . ?
C11 P1 O4 C23 -156.8(4) . . . . ?
O3 P1 O5 C25 159.1(7) . . . . ?
O4 P1 O5 C25 40.5(8) . . . . ?
C11 P1 O5 C25 -66.5(8) . . . . ?
P1 O4 C23 C24 -177.3(4) . . . . ?
P1 O5 C25 C26 -108.6(9) . . . . ?
O3A P1 O5A C25A -161.8(10) . . . . ?
O4 P1 O5A C25A 70.5(10) . . . . ?
C11 P1 O5A C25A -48.4(10) . . . . ?
P1 O4 C23A C24A 155.8(8) . . . . ?
P1 O5A C25A C26A -155.6(14) . . . . ?

_refine_diff_density_max         2.455
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.078

