# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_stu7288
_database_code_depnum_ccdc_archive 'CCDC 1052539'
_audit_update_record             
;
2015-03-06 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H32 Br4 N2'
_chemical_formula_weight         860.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   18.6729(2)
_cell_length_b                   11.08270(10)
_cell_length_c                   33.8570(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7006.58(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    8835
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3408
_exptl_absorpt_coefficient_mu    4.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4159
_exptl_absorpt_correction_T_max  0.9132
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49259
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         4.10
_diffrn_reflns_theta_max         28.07
_reflns_number_total             8457
_reflns_number_gt                6612
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+20.0762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8457
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.46405(2) 0.23079(4) 0.638149(11) 0.04319(10) Uani 1 1 d . . .
Br2 Br 0.25974(2) 0.31872(4) 0.667551(13) 0.04759(11) Uani 1 1 d . . .
Br3 Br 0.49288(2) 0.58770(4) 0.606346(13) 0.04993(12) Uani 1 1 d . . .
Br4 Br 0.26537(2) 0.57024(4) 0.577064(13) 0.04502(11) Uani 1 1 d . . .
N1 N 0.37115(17) 0.2190(3) 0.49189(9) 0.0392(8) Uani 1 1 d . . .
N2 N 0.37871(18) 0.6769(3) 0.74466(10) 0.0432(8) Uani 1 1 d . . .
C1 C 0.36879(19) 0.2737(3) 0.52853(11) 0.0343(8) Uani 1 1 d . . .
C2 C 0.40946(19) 0.2312(3) 0.56053(10) 0.0337(8) Uani 1 1 d . . .
H2 H 0.4375 0.1613 0.5579 0.040 Uiso 1 1 calc R . .
C3 C 0.40793(19) 0.2929(3) 0.59582(10) 0.0327(8) Uani 1 1 d . . .
C4 C 0.36880(19) 0.3979(3) 0.60245(10) 0.0324(8) Uani 1 1 d . . .
C5 C 0.37258(19) 0.4670(3) 0.63987(11) 0.0329(8) Uani 1 1 d . . .
C6 C 0.32660(19) 0.4481(3) 0.67134(11) 0.0343(8) Uani 1 1 d . . .
C7 C 0.3277(2) 0.5145(4) 0.70596(11) 0.0374(9) Uani 1 1 d . . .
H7 H 0.2950 0.4970 0.7263 0.045 Uiso 1 1 calc R . .
C8 C 0.3778(2) 0.6082(3) 0.71052(11) 0.0361(8) Uani 1 1 d . . .
C9 C 0.4253(2) 0.6288(4) 0.67938(11) 0.0383(9) Uani 1 1 d . . .
H9 H 0.4594 0.6910 0.6813 0.046 Uiso 1 1 calc R . .
C10 C 0.42261(19) 0.5590(3) 0.64587(11) 0.0353(8) Uani 1 1 d . . .
C11 C 0.32623(19) 0.4341(3) 0.57075(11) 0.0338(8) Uani 1 1 d . . .
C12 C 0.3249(2) 0.3746(3) 0.53491(11) 0.0351(8) Uani 1 1 d . . .
H12 H 0.2944 0.4018 0.5147 0.042 Uiso 1 1 calc R . .
C13 C 0.4075(2) 0.1046(4) 0.48451(12) 0.0404(9) Uani 1 1 d . . .
H13A H 0.3767 0.0538 0.4680 0.049 Uiso 1 1 calc R . .
H13B H 0.4146 0.0629 0.5097 0.049 Uiso 1 1 calc R . .
C14 C 0.3450(2) 0.2816(4) 0.45725(11) 0.0408(9) Uani 1 1 d . . .
H14A H 0.3746 0.2579 0.4346 0.049 Uiso 1 1 calc R . .
H14B H 0.3518 0.3684 0.4613 0.049 Uiso 1 1 calc R . .
C15 C 0.3247(2) 0.6589(4) 0.77471(12) 0.0444(10) Uani 1 1 d . . .
H15A H 0.2779 0.6522 0.7618 0.053 Uiso 1 1 calc R . .
H15B H 0.3234 0.7305 0.7917 0.053 Uiso 1 1 calc R . .
C16 C 0.4377(2) 0.7577(4) 0.75495(13) 0.0453(10) Uani 1 1 d . . .
H16A H 0.4776 0.7437 0.7367 0.054 Uiso 1 1 calc R . .
H16B H 0.4544 0.7383 0.7817 0.054 Uiso 1 1 calc R . .
C21 C 0.4792(2) 0.1195(3) 0.46436(11) 0.0379(9) Uani 1 1 d . . .
C22 C 0.4927(2) 0.0646(4) 0.42828(12) 0.0442(10) Uani 1 1 d . . .
H22 H 0.4568 0.0176 0.4163 0.053 Uiso 1 1 calc R . .
C23 C 0.5584(3) 0.0780(4) 0.40953(14) 0.0537(12) Uani 1 1 d . . .
H23 H 0.5667 0.0400 0.3851 0.064 Uiso 1 1 calc R . .
C24 C 0.6110(3) 0.1462(4) 0.42646(15) 0.0561(12) Uani 1 1 d . . .
H24 H 0.6552 0.1560 0.4136 0.067 Uiso 1 1 calc R . .
C25 C 0.5990(3) 0.2006(5) 0.46235(15) 0.0591(13) Uani 1 1 d . . .
H25 H 0.6354 0.2461 0.4744 0.071 Uiso 1 1 calc R . .
C26 C 0.5333(2) 0.1885(4) 0.48075(13) 0.0501(11) Uani 1 1 d . . .
H26 H 0.5253 0.2279 0.5049 0.060 Uiso 1 1 calc R . .
C31 C 0.2671(2) 0.2596(4) 0.44682(11) 0.0394(9) Uani 1 1 d . . .
C32 C 0.2286(2) 0.1657(4) 0.46302(13) 0.0492(11) Uani 1 1 d . . .
H32 H 0.2501 0.1158 0.4821 0.059 Uiso 1 1 calc R . .
C33 C 0.1588(3) 0.1441(5) 0.45152(16) 0.0627(13) Uani 1 1 d . . .
H33 H 0.1331 0.0801 0.4629 0.075 Uiso 1 1 calc R . .
C34 C 0.1269(3) 0.2155(5) 0.42358(16) 0.0651(14) Uani 1 1 d . . .
H34 H 0.0797 0.1994 0.4155 0.078 Uiso 1 1 calc R . .
C35 C 0.1639(3) 0.3106(5) 0.40738(14) 0.0631(14) Uani 1 1 d . . .
H35 H 0.1420 0.3605 0.3885 0.076 Uiso 1 1 calc R . .
C36 C 0.2339(3) 0.3324(4) 0.41909(12) 0.0523(11) Uani 1 1 d . . .
H36 H 0.2591 0.3976 0.4080 0.063 Uiso 1 1 calc R . .
C41 C 0.3356(2) 0.5490(4) 0.80053(11) 0.0438(10) Uani 1 1 d . . .
C42 C 0.4015(3) 0.4940(4) 0.80483(13) 0.0517(11) Uani 1 1 d . . .
H42 H 0.4411 0.5236 0.7907 0.062 Uiso 1 1 calc R . .
C43 C 0.4101(3) 0.3956(5) 0.82979(14) 0.0627(13) Uani 1 1 d . . .
H43 H 0.4555 0.3604 0.8330 0.075 Uiso 1 1 calc R . .
C44 C 0.3523(4) 0.3499(5) 0.84973(14) 0.0702(15) Uani 1 1 d . . .
H44 H 0.3579 0.2826 0.8664 0.084 Uiso 1 1 calc R . .
C45 C 0.2866(3) 0.4021(5) 0.84547(15) 0.0731(15) Uani 1 1 d . . .
H45 H 0.2468 0.3704 0.8590 0.088 Uiso 1 1 calc R . .
C46 C 0.2785(3) 0.5017(5) 0.82118(14) 0.0602(13) Uani 1 1 d . . .
H46 H 0.2331 0.5378 0.8187 0.072 Uiso 1 1 calc R . .
C51 C 0.4172(2) 0.8892(4) 0.75342(13) 0.0422(9) Uani 1 1 d . . .
C52 C 0.4226(2) 0.9607(4) 0.78676(15) 0.0549(12) Uani 1 1 d . . .
H52 H 0.4396 0.9271 0.8105 0.066 Uiso 1 1 calc R . .
C53 C 0.4034(3) 1.0810(5) 0.7855(2) 0.0735(16) Uani 1 1 d . . .
H53 H 0.4074 1.1288 0.8084 0.088 Uiso 1 1 calc R . .
C54 C 0.3785(3) 1.1306(5) 0.7513(2) 0.0801(19) Uani 1 1 d . . .
H54 H 0.3652 1.2123 0.7505 0.096 Uiso 1 1 calc R . .
C55 C 0.3731(3) 1.0605(5) 0.71784(19) 0.0701(16) Uani 1 1 d . . .
H55 H 0.3561 1.0948 0.6942 0.084 Uiso 1 1 calc R . .
C56 C 0.3923(2) 0.9396(5) 0.71870(14) 0.0556(12) Uani 1 1 d . . .
H56 H 0.3885 0.8922 0.6958 0.067 Uiso 1 1 calc R . .


_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
Br1 C3 1.904(4) . ?
Br2 C6 1.906(4) . ?
Br3 C10 1.901(4) . ?
Br4 C11 1.901(4) . ?
N1 C1 1.381(5) . ?
N1 C14 1.447(5) . ?
N1 C13 1.459(5) . ?
N2 C8 1.384(5) . ?
N2 C15 1.446(5) . ?
N2 C16 1.462(5) . ?
C1 C12 1.404(5) . ?
C1 C2 1.404(5) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.393(5) . ?
C4 C11 1.394(5) . ?
C4 C5 1.482(5) . ?
C5 C6 1.384(5) . ?
C5 C10 1.397(5) . ?
C6 C7 1.384(5) . ?
C7 C8 1.408(5) . ?
C7 H7 0.9400 . ?
C8 C9 1.397(5) . ?
C9 C10 1.375(5) . ?
C9 H9 0.9400 . ?
C11 C12 1.381(5) . ?
C12 H12 0.9400 . ?
C13 C21 1.512(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C31 1.517(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C41 1.513(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 C51 1.507(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C21 C26 1.384(6) . ?
C21 C22 1.388(5) . ?
C22 C23 1.390(6) . ?
C22 H22 0.9400 . ?
C23 C24 1.366(7) . ?
C23 H23 0.9400 . ?
C24 C25 1.375(7) . ?
C24 H24 0.9400 . ?
C25 C26 1.381(6) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C31 C32 1.378(6) . ?
C31 C36 1.385(5) . ?
C32 C33 1.381(6) . ?
C32 H32 0.9400 . ?
C33 C34 1.370(7) . ?
C33 H33 0.9400 . ?
C34 C35 1.375(7) . ?
C34 H34 0.9400 . ?
C35 C36 1.387(7) . ?
C35 H35 0.9400 . ?
C36 H36 0.9400 . ?
C41 C46 1.379(6) . ?
C41 C42 1.382(6) . ?
C42 C43 1.389(6) . ?
C42 H42 0.9400 . ?
C43 C44 1.371(7) . ?
C43 H43 0.9400 . ?
C44 C45 1.364(8) . ?
C44 H44 0.9400 . ?
C45 C46 1.385(7) . ?
C45 H45 0.9400 . ?
C46 H46 0.9400 . ?
C51 C56 1.382(6) . ?
C51 C52 1.383(6) . ?
C52 C53 1.381(7) . ?
C52 H52 0.9400 . ?
C53 C54 1.365(8) . ?
C53 H53 0.9400 . ?
C54 C55 1.377(8) . ?
C54 H54 0.9400 . ?
C55 C56 1.387(7) . ?
C55 H55 0.9400 . ?
C56 H56 0.9400 . ?

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 C14 120.4(3) . . ?
C1 N1 C13 123.3(3) . . ?
C14 N1 C13 115.8(3) . . ?
C8 N2 C15 120.2(3) . . ?
C8 N2 C16 123.0(3) . . ?
C15 N2 C16 116.3(3) . . ?
N1 C1 C12 120.4(3) . . ?
N1 C1 C2 121.9(3) . . ?
C12 C1 C2 117.7(3) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 124.4(3) . . ?
C2 C3 Br1 117.6(3) . . ?
C4 C3 Br1 118.0(3) . . ?
C3 C4 C11 114.5(3) . . ?
C3 C4 C5 123.0(3) . . ?
C11 C4 C5 122.5(3) . . ?
C6 C5 C10 114.4(3) . . ?
C6 C5 C4 123.4(3) . . ?
C10 C5 C4 122.2(3) . . ?
C7 C6 C5 124.3(3) . . ?
C7 C6 Br2 117.8(3) . . ?
C5 C6 Br2 117.9(3) . . ?
C6 C7 C8 119.6(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
N2 C8 C9 122.2(4) . . ?
N2 C8 C7 120.4(4) . . ?
C9 C8 C7 117.4(3) . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 123.8(3) . . ?
C9 C10 Br3 117.4(3) . . ?
C5 C10 Br3 118.8(3) . . ?
C12 C11 C4 123.3(3) . . ?
C12 C11 Br4 117.8(3) . . ?
C4 C11 Br4 118.8(3) . . ?
C11 C12 C1 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C1 C12 H12 119.8 . . ?
N1 C13 C21 113.2(3) . . ?
N1 C13 H13A 108.9 . . ?
C21 C13 H13A 108.9 . . ?
N1 C13 H13B 108.9 . . ?
C21 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N1 C14 C31 115.8(3) . . ?
N1 C14 H14A 108.3 . . ?
C31 C14 H14A 108.3 . . ?
N1 C14 H14B 108.3 . . ?
C31 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
N2 C15 C41 115.1(3) . . ?
N2 C15 H15A 108.5 . . ?
C41 C15 H15A 108.5 . . ?
N2 C15 H15B 108.5 . . ?
C41 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
N2 C16 C51 113.1(3) . . ?
N2 C16 H16A 109.0 . . ?
C51 C16 H16A 109.0 . . ?
N2 C16 H16B 109.0 . . ?
C51 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C26 C21 C22 117.6(4) . . ?
C26 C21 C13 121.8(4) . . ?
C22 C21 C13 120.7(4) . . ?
C21 C22 C23 121.0(4) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 120.2(4) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.8(5) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.0(5) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 121.4(4) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
C32 C31 C36 118.5(4) . . ?
C32 C31 C14 121.9(4) . . ?
C36 C31 C14 119.5(4) . . ?
C31 C32 C33 120.7(4) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C34 C33 C32 120.4(5) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 119.9(5) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C36 119.6(5) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C31 C36 C35 120.9(5) . . ?
C31 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C46 C41 C42 118.0(4) . . ?
C46 C41 C15 119.7(4) . . ?
C42 C41 C15 122.4(4) . . ?
C41 C42 C43 120.9(5) . . ?
C41 C42 H42 119.6 . . ?
C43 C42 H42 119.6 . . ?
C44 C43 C42 119.9(5) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C45 C44 C43 120.0(5) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 119.9(5) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C41 C46 C45 121.3(5) . . ?
C41 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C56 C51 C52 119.2(4) . . ?
C56 C51 C16 120.4(4) . . ?
C52 C51 C16 120.4(4) . . ?
C53 C52 C51 120.6(5) . . ?
C53 C52 H52 119.7 . . ?
C51 C52 H52 119.7 . . ?
C54 C53 C52 120.2(5) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C53 C54 C55 119.8(5) . . ?
C53 C54 H54 120.1 . . ?
C55 C54 H54 120.1 . . ?
C54 C55 C56 120.5(5) . . ?
C54 C55 H55 119.7 . . ?
C56 C55 H55 119.7 . . ?
C51 C56 C55 119.7(5) . . ?
C51 C56 H56 120.1 . . ?
C55 C56 H56 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
C14 N1 C1 C12 17.1(5) . . . . ?
C13 N1 C1 C12 -171.1(4) . . . . ?
C14 N1 C1 C2 -163.1(4) . . . . ?
C13 N1 C1 C2 8.7(6) . . . . ?
N1 C1 C2 C3 176.7(4) . . . . ?
C12 C1 C2 C3 -3.5(5) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C1 C2 C3 Br1 179.9(3) . . . . ?
C2 C3 C4 C11 3.9(5) . . . . ?
Br1 C3 C4 C11 -176.8(3) . . . . ?
C2 C3 C4 C5 -175.3(4) . . . . ?
Br1 C3 C4 C5 4.0(5) . . . . ?
C3 C4 C5 C6 -91.9(5) . . . . ?
C11 C4 C5 C6 88.9(5) . . . . ?
C3 C4 C5 C10 89.3(5) . . . . ?
C11 C4 C5 C10 -89.8(5) . . . . ?
C10 C5 C6 C7 1.2(6) . . . . ?
C4 C5 C6 C7 -177.6(4) . . . . ?
C10 C5 C6 Br2 -176.5(3) . . . . ?
C4 C5 C6 Br2 4.7(5) . . . . ?
C5 C6 C7 C8 0.2(6) . . . . ?
Br2 C6 C7 C8 177.9(3) . . . . ?
C15 N2 C8 C9 174.9(4) . . . . ?
C16 N2 C8 C9 -13.7(6) . . . . ?
C15 N2 C8 C7 -4.6(6) . . . . ?
C16 N2 C8 C7 166.8(4) . . . . ?
C6 C7 C8 N2 178.8(4) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
N2 C8 C9 C10 -179.7(4) . . . . ?
C7 C8 C9 C10 -0.3(6) . . . . ?
C8 C9 C10 C5 1.9(6) . . . . ?
C8 C9 C10 Br3 -176.5(3) . . . . ?
C6 C5 C10 C9 -2.2(6) . . . . ?
C4 C5 C10 C9 176.6(4) . . . . ?
C6 C5 C10 Br3 176.1(3) . . . . ?
C4 C5 C10 Br3 -5.0(5) . . . . ?
C3 C4 C11 C12 -2.8(5) . . . . ?
C5 C4 C11 C12 176.4(4) . . . . ?
C3 C4 C11 Br4 176.0(3) . . . . ?
C5 C4 C11 Br4 -4.8(5) . . . . ?
C4 C11 C12 C1 -1.4(6) . . . . ?
Br4 C11 C12 C1 179.8(3) . . . . ?
N1 C1 C12 C11 -175.6(4) . . . . ?
C2 C1 C12 C11 4.6(5) . . . . ?
C1 N1 C13 C21 -102.7(4) . . . . ?
C14 N1 C13 C21 69.4(4) . . . . ?
C1 N1 C14 C31 -92.1(4) . . . . ?
C13 N1 C14 C31 95.5(4) . . . . ?
C8 N2 C15 C41 77.3(5) . . . . ?
C16 N2 C15 C41 -94.7(4) . . . . ?
C8 N2 C16 C51 111.8(4) . . . . ?
C15 N2 C16 C51 -76.5(5) . . . . ?
N1 C13 C21 C26 57.8(5) . . . . ?
N1 C13 C21 C22 -121.6(4) . . . . ?
C26 C21 C22 C23 0.4(6) . . . . ?
C13 C21 C22 C23 179.9(4) . . . . ?
C21 C22 C23 C24 -0.2(7) . . . . ?
C22 C23 C24 C25 0.7(7) . . . . ?
C23 C24 C25 C26 -1.5(7) . . . . ?
C24 C25 C26 C21 1.8(7) . . . . ?
C22 C21 C26 C25 -1.2(7) . . . . ?
C13 C21 C26 C25 179.4(4) . . . . ?
N1 C14 C31 C32 -14.9(6) . . . . ?
N1 C14 C31 C36 167.7(4) . . . . ?
C36 C31 C32 C33 0.7(6) . . . . ?
C14 C31 C32 C33 -176.8(4) . . . . ?
C31 C32 C33 C34 0.4(7) . . . . ?
C32 C33 C34 C35 -1.2(8) . . . . ?
C33 C34 C35 C36 0.9(8) . . . . ?
C32 C31 C36 C35 -0.9(6) . . . . ?
C14 C31 C36 C35 176.5(4) . . . . ?
C34 C35 C36 C31 0.1(7) . . . . ?
N2 C15 C41 C46 -159.8(4) . . . . ?
N2 C15 C41 C42 21.1(6) . . . . ?
C46 C41 C42 C43 -1.2(7) . . . . ?
C15 C41 C42 C43 177.9(4) . . . . ?
C41 C42 C43 C44 1.7(7) . . . . ?
C42 C43 C44 C45 -0.9(8) . . . . ?
C43 C44 C45 C46 -0.5(8) . . . . ?
C42 C41 C46 C45 -0.1(7) . . . . ?
C15 C41 C46 C45 -179.2(4) . . . . ?
C44 C45 C46 C41 1.0(8) . . . . ?
N2 C16 C51 C56 -59.2(5) . . . . ?
N2 C16 C51 C52 120.4(4) . . . . ?
C56 C51 C52 C53 0.1(7) . . . . ?
C16 C51 C52 C53 -179.5(4) . . . . ?
C51 C52 C53 C54 0.2(8) . . . . ?
C52 C53 C54 C55 -0.3(8) . . . . ?
C53 C54 C55 C56 0.3(8) . . . . ?
C52 C51 C56 C55 -0.2(7) . . . . ?
C16 C51 C56 C55 179.4(4) . . . . ?
C54 C55 C56 C51 0.0(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.07
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.087
####################################################################### 
# 
# 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_stu7460
_database_code_depnum_ccdc_archive 'CCDC 1052540'
_audit_update_record             
;
2015-03-06 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H42 N2 O2 P2'
_chemical_formula_weight         788.82

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   28.1262(5)
_cell_length_b                   8.5442(2)
_cell_length_c                   20.5029(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.7190(10)
_cell_angle_gamma                90.00
_cell_volume                     4638.24(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4707
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13982
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.22
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4013
_reflns_number_gt                2997
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

 A badly disordered half dichloromethane molecule was found in the 
 asymmetrical unit and could not be satisfactorily refined. The program 
 SQUEEZE (A. L. Spek J. Appl. Cryst., 2003, 36, 7-13) was therefore used to
 remove mathematically the effect of the solvent.
 The quoted formula and derived parameters are not included the squeezed
 solvent molecule. 
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 183 21 ' '
2 0.000 0.000 0.500 183 21 ' '
3 0.500 0.499 1.000 183 21 ' '
4 0.500 0.499 0.500 183 21 ' '

_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)+(0.0979P)²+9.2005P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4013
_refine_ls_number_parameters     262
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2121
_refine_ls_wR_factor_gt          0.1963
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.079
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.20975(3) 0.85098(10) 0.08248(4) 0.0376(3) Uani 1 1 d . . .
O1 O 0.17567(9) 0.7778(3) 0.11466(12) 0.0526(7) Uani 1 1 d . . .
N1 N 0.11045(12) 0.9471(4) -0.19131(14) 0.0550(9) Uani 1 1 d . . .
C1 C 0.19060(12) 0.8506(4) -0.01269(16) 0.0380(7) Uani 1 1 d . . .
C2 C 0.14981(12) 0.9046(4) -0.06757(17) 0.0402(8) Uani 1 1 d . . .
H2 H 0.1225 0.9538 -0.0593 0.048 Uiso 1 1 calc R . .
C3 C 0.14972(12) 0.8848(4) -0.13625(16) 0.0425(8) Uani 1 1 d . . .
C4 C 0.22874(12) 0.7769(4) -0.02852(16) 0.0380(7) Uani 1 1 d . . .
C5 C 0.26942(12) 0.7475(4) 0.09416(16) 0.0383(7) Uani 1 1 d . . .
C6 C 0.31002(12) 0.6925(4) 0.14909(16) 0.0403(8) Uani 1 1 d . . .
H6 H 0.3107 0.7067 0.1949 0.048 Uiso 1 1 calc R . .
C7 C 0.06945(14) 1.0303(5) -0.17847(19) 0.0549(10) Uani 1 1 d . . .
H7A H 0.0552 0.9624 -0.1512 0.066 Uiso 1 1 calc R . .
H7B H 0.0429 1.0497 -0.2230 0.066 Uiso 1 1 calc R . .
C8 C 0.10914(15) 0.9216(5) -0.26190(17) 0.0539(10) Uani 1 1 d . . .
H8A H 0.1415 0.9547 -0.2655 0.065 Uiso 1 1 calc R . .
H8B H 0.0828 0.9883 -0.2930 0.065 Uiso 1 1 calc R . .
C11 C 0.22698(12) 1.0484(4) 0.11092(17) 0.0392(8) Uani 1 1 d . . .
C12 C 0.21306(15) 1.1769(4) 0.06751(19) 0.0504(9) Uani 1 1 d . . .
H12 H 0.1950 1.1631 0.0201 0.060 Uiso 1 1 calc R . .
C13 C 0.22595(18) 1.3261(5) 0.0944(2) 0.0637(11) Uani 1 1 d . . .
H13 H 0.2165 1.4138 0.0652 0.076 Uiso 1 1 calc R . .
C14 C 0.25258(17) 1.3459(5) 0.1638(2) 0.0608(11) Uani 1 1 d . . .
H14 H 0.2609 1.4475 0.1816 0.073 Uiso 1 1 calc R . .
C15 C 0.26705(15) 1.2205(5) 0.2071(2) 0.0533(10) Uani 1 1 d . . .
H15 H 0.2853 1.2352 0.2545 0.064 Uiso 1 1 calc R . .
C16 C 0.25463(13) 1.0718(5) 0.18071(17) 0.0471(9) Uani 1 1 d . . .
H16 H 0.2650 0.9849 0.2102 0.057 Uiso 1 1 calc R . .
C21 C 0.08382(13) 1.1833(5) -0.14116(19) 0.0483(9) Uani 1 1 d . . .
C22 C 0.05964(18) 1.2352(6) -0.0967(3) 0.0716(13) Uani 1 1 d . . .
H22 H 0.0336 1.1740 -0.0910 0.086 Uiso 1 1 calc R . .
C23 C 0.0725(3) 1.3739(7) -0.0605(4) 0.0994(19) Uani 1 1 d . . .
H23 H 0.0562 1.4049 -0.0294 0.119 Uiso 1 1 calc R . .
C24 C 0.1093(2) 1.4653(6) -0.0704(4) 0.0926(17) Uani 1 1 d . . .
H24 H 0.1166 1.5634 -0.0485 0.111 Uiso 1 1 calc R . .
C25 C 0.1347(2) 1.4167(6) -0.1107(4) 0.103(2) Uani 1 1 d . . .
H25 H 0.1615 1.4773 -0.1147 0.124 Uiso 1 1 calc R . .
C26 C 0.12186(19) 1.2758(6) -0.1472(3) 0.0840(16) Uani 1 1 d . . .
H26 H 0.1397 1.2440 -0.1763 0.101 Uiso 1 1 calc R . .
C31 C 0.09923(14) 0.7541(5) -0.28646(18) 0.0550(10) Uani 1 1 d . . .
C32 C 0.0635(2) 0.6653(7) -0.2723(3) 0.0835(15) Uani 1 1 d . . .
H32 H 0.0455 0.7083 -0.2454 0.100 Uiso 1 1 calc R . .
C33 C 0.0532(3) 0.5142(9) -0.2964(3) 0.116(2) Uani 1 1 d U . .
H33 H 0.0279 0.4559 -0.2871 0.139 Uiso 1 1 calc R . .
C34 C 0.0805(3) 0.4491(8) -0.3348(3) 0.105(2) Uani 1 1 d . . .
H34 H 0.0744 0.3454 -0.3507 0.126 Uiso 1 1 calc R . .
C35 C 0.1163(2) 0.5362(7) -0.3490(3) 0.0836(15) Uani 1 1 d . . .
H35 H 0.1347 0.4928 -0.3753 0.100 Uiso 1 1 calc R . .
C36 C 0.12563(16) 0.6877(6) -0.3253(2) 0.0651(12) Uani 1 1 d . . .
H36 H 0.1504 0.7468 -0.3356 0.078 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.474(3) . ?
P1 C11 1.797(3) . ?
P1 C5 1.840(3) . ?
P1 C1 1.841(3) . ?
N1 C3 1.391(4) . ?
N1 C8 1.452(4) . ?
N1 C7 1.452(5) . ?
C1 C4 1.374(5) . ?
C1 C2 1.387(4) . ?
C2 C3 1.417(5) . ?
C2 H2 0.9400 . ?
C3 C6 1.410(5) 7_565 ?
C4 C5 1.380(5) 7_565 ?
C4 C4 1.437(6) 7_565 ?
C5 C4 1.380(5) 7_565 ?
C5 C6 1.388(4) . ?
C6 C3 1.410(5) 7_565 ?
C6 H6 0.9400 . ?
C7 C21 1.500(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C31 1.511(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C11 C12 1.384(5) . ?
C11 C16 1.393(5) . ?
C12 C13 1.388(6) . ?
C12 H12 0.9400 . ?
C13 C14 1.376(6) . ?
C13 H13 0.9400 . ?
C14 C15 1.364(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.379(5) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C21 C26 1.369(6) . ?
C21 C22 1.381(6) . ?
C22 C23 1.381(7) . ?
C22 H22 0.9400 . ?
C23 C24 1.364(8) . ?
C23 H23 0.9400 . ?
C24 C25 1.330(8) . ?
C24 H24 0.9400 . ?
C25 C26 1.400(8) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C31 C32 1.367(6) . ?
C31 C36 1.380(6) . ?
C32 C33 1.378(9) . ?
C32 H32 0.9400 . ?
C33 C34 1.388(9) . ?
C33 H33 0.9400 . ?
C34 C35 1.359(8) . ?
C34 H34 0.9400 . ?
C35 C36 1.377(7) . ?
C35 H35 0.9400 . ?
C36 H36 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C11 113.44(16) . . ?
O1 P1 C5 116.12(15) . . ?
C11 P1 C5 105.94(15) . . ?
O1 P1 C1 118.16(15) . . ?
C11 P1 C1 107.22(15) . . ?
C5 P1 C1 93.73(14) . . ?
C3 N1 C8 119.8(3) . . ?
C3 N1 C7 120.1(3) . . ?
C8 N1 C7 120.0(3) . . ?
C4 C1 C2 117.3(3) . . ?
C4 C1 P1 106.2(2) . . ?
C2 C1 P1 136.5(3) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N1 C3 C6 119.7(3) . 7_565 ?
N1 C3 C2 119.7(3) . . ?
C6 C3 C2 120.6(3) 7_565 . ?
C1 C4 C5 126.1(3) . 7_565 ?
C1 C4 C4 117.1(4) . 7_565 ?
C5 C4 C4 116.8(4) 7_565 7_565 ?
C4 C5 C6 116.7(3) 7_565 . ?
C4 C5 P1 106.2(2) 7_565 . ?
C6 C5 P1 137.2(3) . . ?
C5 C6 C3 120.0(3) . 7_565 ?
C5 C6 H6 120.0 . . ?
C3 C6 H6 120.0 7_565 . ?
N1 C7 C21 115.2(3) . . ?
N1 C7 H7A 108.5 . . ?
C21 C7 H7A 108.5 . . ?
N1 C7 H7B 108.5 . . ?
C21 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
N1 C8 C31 114.5(3) . . ?
N1 C8 H8A 108.6 . . ?
C31 C8 H8A 108.6 . . ?
N1 C8 H8B 108.6 . . ?
C31 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C12 C11 C16 119.0(3) . . ?
C12 C11 P1 123.3(3) . . ?
C16 C11 P1 117.6(3) . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 121.1(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.2(4) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C11 121.0(4) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C26 C21 C22 116.6(4) . . ?
C26 C21 C7 122.8(4) . . ?
C22 C21 C7 120.5(4) . . ?
C21 C22 C23 122.2(4) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
C24 C23 C22 119.0(5) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 120.6(5) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.3(5) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 121.2(5) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C32 C31 C36 118.2(5) . . ?
C32 C31 C8 121.4(4) . . ?
C36 C31 C8 120.4(4) . . ?
C31 C32 C33 121.6(5) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C32 C33 C34 119.3(6) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C35 C34 C33 119.6(6) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 120.4(5) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 121.0(5) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?

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
O1 P1 C1 C4 -122.7(2) . . . . ?
C11 P1 C1 C4 107.6(2) . . . . ?
C5 P1 C1 C4 -0.3(3) . . . . ?
O1 P1 C1 C2 57.8(4) . . . . ?
C11 P1 C1 C2 -71.8(4) . . . . ?
C5 P1 C1 C2 -179.8(4) . . . . ?
C4 C1 C2 C3 -1.3(5) . . . . ?
P1 C1 C2 C3 178.1(3) . . . . ?
C8 N1 C3 C6 4.8(5) . . . 7_565 ?
C7 N1 C3 C6 -178.5(3) . . . 7_565 ?
C8 N1 C3 C2 -177.5(3) . . . . ?
C7 N1 C3 C2 -0.8(5) . . . . ?
C1 C2 C3 N1 -176.1(3) . . . . ?
C1 C2 C3 C6 1.6(5) . . . 7_565 ?
C2 C1 C4 C5 0.6(5) . . . 7_565 ?
P1 C1 C4 C5 -179.0(3) . . . 7_565 ?
C2 C1 C4 C4 179.2(4) . . . 7_565 ?
P1 C1 C4 C4 -0.4(5) . . . 7_565 ?
O1 P1 C5 C4 125.0(2) . . . 7_565 ?
C11 P1 C5 C4 -108.1(2) . . . 7_565 ?
C1 P1 C5 C4 1.0(2) . . . 7_565 ?
O1 P1 C5 C6 -55.2(4) . . . . ?
C11 P1 C5 C6 71.7(4) . . . . ?
C1 P1 C5 C6 -179.2(4) . . . . ?
C4 C5 C6 C3 -0.4(5) 7_565 . . 7_565 ?
P1 C5 C6 C3 179.8(3) . . . 7_565 ?
C3 N1 C7 C21 67.7(5) . . . . ?
C8 N1 C7 C21 -115.6(4) . . . . ?
C3 N1 C8 C31 68.4(5) . . . . ?
C7 N1 C8 C31 -108.4(4) . . . . ?
O1 P1 C11 C12 -114.7(3) . . . . ?
C5 P1 C11 C12 116.8(3) . . . . ?
C1 P1 C11 C12 17.6(3) . . . . ?
O1 P1 C11 C16 63.6(3) . . . . ?
C5 P1 C11 C16 -65.0(3) . . . . ?
C1 P1 C11 C16 -164.1(3) . . . . ?
C16 C11 C12 C13 -1.3(5) . . . . ?
P1 C11 C12 C13 177.0(3) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 C15 0.5(7) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C14 C15 C16 C11 -1.0(6) . . . . ?
C12 C11 C16 C15 1.7(5) . . . . ?
P1 C11 C16 C15 -176.7(3) . . . . ?
N1 C7 C21 C26 30.3(5) . . . . ?
N1 C7 C21 C22 -147.6(4) . . . . ?
C26 C21 C22 C23 0.7(7) . . . . ?
C7 C21 C22 C23 178.7(5) . . . . ?
C21 C22 C23 C24 2.0(9) . . . . ?
C22 C23 C24 C25 -4.5(10) . . . . ?
C23 C24 C25 C26 4.3(11) . . . . ?
C22 C21 C26 C25 -0.9(7) . . . . ?
C7 C21 C26 C25 -179.0(5) . . . . ?
C24 C25 C26 C21 -1.5(10) . . . . ?
N1 C8 C31 C32 42.6(5) . . . . ?
N1 C8 C31 C36 -138.6(4) . . . . ?
C36 C31 C32 C33 -0.9(8) . . . . ?
C8 C31 C32 C33 177.9(5) . . . . ?
C31 C32 C33 C34 1.5(10) . . . . ?
C32 C33 C34 C35 -1.3(11) . . . . ?
C33 C34 C35 C36 0.5(9) . . . . ?
C34 C35 C36 C31 0.2(8) . . . . ?
C32 C31 C36 C35 0.0(6) . . . . ?
C8 C31 C36 C35 -178.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_stu7852
_database_code_depnum_ccdc_archive 'CCDC 1052541'
_audit_update_record             
;
2015-03-06 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H34 Br2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         702.51

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.0372(6)
_cell_length_b                   12.6734(7)
_cell_length_c                   13.6066(7)
_cell_angle_alpha                87.925(2)
_cell_angle_beta                 67.674(2)
_cell_angle_gamma                66.578(2)
_cell_volume                     1600.69(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9713
_cell_measurement_theta_min      3.5441
_cell_measurement_theta_max      68.3514
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.127
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716

_exptl_absorpt_coefficient_mu    3.444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.67

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            45014
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         68.45
_diffrn_reflns_theta_full        68.45
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             5859
_reflns_number_gt                5575
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0674
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         5859
_refine_ls_number_parameters     410
_refine_ls_number_restraints     17
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²+1.9107P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.571
_refine_diff_density_min         -0.345
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.23246(17) 0.27927(14) 0.72792(13) 0.0166(3) Uani d . . . 1.0 . .
N N2 0.35345(18) 0.79120(14) 0.15905(13) 0.0187(3) Uani d . . . 1.0 . .
C C1 0.3062(2) 0.48951(17) 0.48182(15) 0.0173(4) Uani d . . . 1.0 . .
C C2 0.2117(2) 0.53623(17) 0.58770(16) 0.0172(4) Uani d . . D 1.0 . .
H H6A 0.1616 0.6183 0.6044 0.021 Uiso calc U P DR 0.0410(9) A 1
C C6 0.3760(2) 0.36896(18) 0.46240(16) 0.0193(4) Uani d . . D 1.0 . .
Br Br1 0.10600(2) 0.69930(2) 0.62313(2) 0.02388(8) Uani d U P D 0.9590(9) A 1
H H6 0.443(3) 0.335(2) 0.3900(13) 0.029 Uiso d U P D 0.9590(9) A 1
Br Br1A 0.5003(6) 0.3363(5) 0.3392(4) 0.0272(18) Uani d U P D 0.0410(9) A 2
C C3 0.1866(2) 0.46999(17) 0.66994(15) 0.0165(4) Uani d . . . 1.0 . .
H H3 0.123 0.5067 0.7411 0.02 Uiso calc U . R 1.0 . .
C C4 0.2556(2) 0.34830(17) 0.64799(15) 0.0156(4) Uani d . . . 1.0 . .
C C5 0.3515(2) 0.29939(17) 0.54157(16) 0.0181(4) Uani d . . . 1.0 . .
H H5 0.4001 0.2174 0.5239 0.022 Uiso calc U . R 1.0 . .
C C7 0.3253(2) 0.56319(17) 0.39407(15) 0.0176(4) Uani d . . . 1.0 . .
C C8 0.2426(2) 0.58881(17) 0.33338(15) 0.0167(4) Uani d . . . 1.0 . .
C C12 0.4227(2) 0.61384(18) 0.37032(16) 0.0205(4) Uani d . . . 1.0 . .
H H12 0.4835 0.5968 0.4082 0.025 Uiso calc U . R 1.0 . .
Br Br2 0.10458(2) 0.52557(2) 0.36057(2) 0.01906(7) Uani d . . . 1.0 . .
C C9 0.2535(2) 0.66019(16) 0.25398(15) 0.0166(4) Uani d . . . 1.0 . .
H H9 0.1974 0.6723 0.2128 0.02 Uiso calc U . R 1.0 . .
C C10 0.3479(2) 0.71485(17) 0.23423(15) 0.0174(4) Uani d . . . 1.0 . .
C C11 0.4343(2) 0.68824(18) 0.29338(16) 0.0202(4) Uani d . . . 1.0 . .
H H11 0.5013 0.7216 0.2805 0.024 Uiso calc U . R 1.0 . .
C C13 0.1075(2) 0.32286(17) 0.83115(15) 0.0179(4) Uani d . . . 1.0 . .
H H13A 0.0588 0.2697 0.8452 0.021 Uiso calc U . R 1.0 . .
H H13B 0.0384 0.3999 0.8263 0.021 Uiso calc U . R 1.0 . .
C C14 0.3104(2) 0.15372(17) 0.70505(16) 0.0180(4) Uani d . . . 1.0 . .
H H14A 0.3128 0.1229 0.7725 0.022 Uiso calc U . R 1.0 . .
H H14B 0.4111 0.1346 0.655 0.022 Uiso calc U . R 1.0 . .
C C15 0.4646(2) 0.83470(17) 0.12255(15) 0.0185(4) Uani d . . . 1.0 . .
H H15A 0.492 0.8399 0.0449 0.022 Uiso calc U . R 1.0 . .
H H15B 0.5508 0.7778 0.1319 0.022 Uiso calc U . R 1.0 . .
C C16 0.2402(2) 0.84220(18) 0.12018(16) 0.0209(4) Uani d . . . 1.0 . .
H H16A 0.2257 0.9235 0.1105 0.025 Uiso calc U . R 1.0 . .
H H16B 0.1497 0.844 0.1758 0.025 Uiso calc U . R 1.0 . .
C C21 0.1465(2) 0.33380(17) 0.92454(15) 0.0185(4) Uani d . . . 1.0 . .
C C22 0.1381(2) 0.25772(19) 1.00087(16) 0.0245(4) Uani d . . . 1.0 . .
H H22 0.1069 0.1994 0.9944 0.029 Uiso calc U . R 1.0 . .
C C23 0.1748(2) 0.2662(2) 1.08648(17) 0.0309(5) Uani d . . . 1.0 . .
H H23 0.1693 0.2135 1.1377 0.037 Uiso calc U . R 1.0 . .
C C24 0.2191(3) 0.3513(2) 1.09687(17) 0.0316(5) Uani d . . . 1.0 . .
H H24 0.2439 0.3573 1.1554 0.038 Uiso calc U . R 1.0 . .
C C25 0.2274(2) 0.42769(19) 1.02206(18) 0.0289(5) Uani d . . . 1.0 . .
H H25 0.2575 0.4865 1.0295 0.035 Uiso calc U . R 1.0 . .
C C26 0.1919(2) 0.41875(18) 0.93596(17) 0.0226(4) Uani d . . . 1.0 . .
H H26 0.1987 0.4711 0.8845 0.027 Uiso calc U . R 1.0 . .
C C31 0.2484(2) 0.09175(17) 0.65674(15) 0.0174(4) Uani d . . . 1.0 . .
C C32 0.3185(2) -0.02866(19) 0.63003(18) 0.0266(5) Uani d . . . 1.0 . .
H H32 0.4049 -0.0701 0.6403 0.032 Uiso calc U . R 1.0 . .
C C33 0.2634(3) -0.08814(19) 0.5888(2) 0.0309(5) Uani d . . . 1.0 . .
H H33 0.3127 -0.17 0.5699 0.037 Uiso calc U . R 1.0 . .
C C34 0.1356(2) -0.02848(19) 0.57480(18) 0.0257(5) Uani d . . . 1.0 . .
H H34 0.0966 -0.0695 0.5478 0.031 Uiso calc U . R 1.0 . .
C C35 0.0662(2) 0.09067(18) 0.60044(16) 0.0210(4) Uani d . . . 1.0 . .
H H35 -0.0207 0.1318 0.5908 0.025 Uiso calc U . R 1.0 . .
C C36 0.1229(2) 0.15074(17) 0.64042(16) 0.0188(4) Uani d . . . 1.0 . .
H H36 0.0754 0.2329 0.6567 0.023 Uiso calc U . R 1.0 . .
C C41 0.4220(2) 0.95234(17) 0.17991(15) 0.0168(4) Uani d . . . 1.0 . .
C C42 0.3064(2) 0.99806(19) 0.27862(16) 0.0229(4) Uani d . . . 1.0 . .
H H42 0.2506 0.9558 0.3114 0.028 Uiso calc U . R 1.0 . .
C C43 0.2722(2) 1.10527(19) 0.32967(17) 0.0273(5) Uani d . . . 1.0 . .
H H43 0.193 1.1359 0.397 0.033 Uiso calc U . R 1.0 . .
C C44 0.3528(3) 1.16749(19) 0.28290(18) 0.0265(5) Uani d . . . 1.0 . .
H H44 0.3287 1.241 0.3177 0.032 Uiso calc U . R 1.0 . .
C C45 0.4688(2) 1.12216(18) 0.18522(17) 0.0240(4) Uani d . . . 1.0 . .
H H45 0.5253 1.1642 0.1533 0.029 Uiso calc U . R 1.0 . .
C C46 0.5028(2) 1.01560(18) 0.13379(16) 0.0197(4) Uani d . . . 1.0 . .
H H46 0.582 0.9854 0.0664 0.024 Uiso calc U . R 1.0 . .
C C51 0.2673(2) 0.78004(19) 0.01522(16) 0.0212(4) Uani d . . . 1.0 . .
C C52 0.3776(2) 0.67141(19) -0.02958(18) 0.0257(5) Uani d . . . 1.0 . .
H H52 0.439 0.6327 0.006 0.031 Uiso calc U . R 1.0 . .
C C53 0.3997(3) 0.6181(2) -0.12658(19) 0.0317(5) Uani d . . . 1.0 . .
H H53 0.476 0.5435 -0.1565 0.038 Uiso calc U . R 1.0 . .
C C54 0.3115(3) 0.6729(2) -0.17917(19) 0.0359(6) Uani d . . . 1.0 . .
H H54 0.3264 0.6361 -0.2449 0.043 Uiso calc U . R 1.0 . .
C C55 0.2012(3) 0.7817(3) -0.1356(2) 0.0409(6) Uani d . . . 1.0 . .
H H55 0.1399 0.82 -0.1714 0.049 Uiso calc U . R 1.0 . .
C C56 0.1799(3) 0.8351(2) -0.03926(19) 0.0345(5) Uani d . . . 1.0 . .
H H56 0.1046 0.9102 -0.0102 0.041 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C4 . 1.382(2) ?
N1 C14 . 1.454(2) ?
N1 C13 . 1.469(2) ?
N2 C10 . 1.384(2) ?
N2 C16 . 1.448(3) ?
N2 C15 . 1.453(2) ?
C1 C6 . 1.392(3) ?
C1 C2 . 1.394(3) ?
C1 C7 . 1.492(3) ?
C2 C3 . 1.384(3) ?
C2 Br1 . 1.8953(19) ?
C2 H6A . 0.95 ?
C6 C5 . 1.382(3) ?
C6 Br1A . 1.648(5) ?
C6 H6 . 0.961(14) ?
Br1A C54 2_665 2.336(6) ?
C3 C4 . 1.405(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.407(3) ?
C5 H5 . 0.95 ?
C7 C8 . 1.392(3) ?
C7 C12 . 1.394(3) ?
C8 C9 . 1.385(3) ?
C8 Br2 . 1.9030(19) ?
C12 C11 . 1.387(3) ?
C12 H12 . 0.95 ?
C9 C10 . 1.408(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.406(3) ?
C11 H11 . 0.95 ?
C13 C21 . 1.515(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C31 . 1.525(3) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C41 . 1.517(3) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C51 . 1.523(3) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C21 C26 . 1.391(3) ?
C21 C22 . 1.394(3) ?
C22 C23 . 1.391(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.380(4) ?
C23 H23 . 0.95 ?
C24 C25 . 1.382(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.390(3) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C31 C36 . 1.387(3) ?
C31 C32 . 1.395(3) ?
C32 C33 . 1.381(3) ?
C32 H32 . 0.95 ?
C33 C34 . 1.394(3) ?
C33 H33 . 0.95 ?
C34 C35 . 1.380(3) ?
C34 H34 . 0.95 ?
C35 C36 . 1.392(3) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C41 C42 . 1.390(3) ?
C41 C46 . 1.393(3) ?
C42 C43 . 1.390(3) ?
C42 H42 . 0.95 ?
C43 C44 . 1.382(3) ?
C43 H43 . 0.95 ?
C44 C45 . 1.383(3) ?
C44 H44 . 0.95 ?
C45 C46 . 1.386(3) ?
C45 H45 . 0.95 ?
C46 H46 . 0.95 ?
C51 C52 . 1.383(3) ?
C51 C56 . 1.392(3) ?
C52 C53 . 1.396(3) ?
C52 H52 . 0.95 ?
C53 C54 . 1.378(4) ?
C53 H53 . 0.95 ?
C54 C55 . 1.383(4) ?
C54 Br1A 2_665 2.336(6) ?
C54 H54 . 0.95 ?
C55 C56 . 1.391(3) ?
C55 H55 . 0.95 ?
C56 H56 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 C14 . . 120.80(16) ?
C4 N1 C13 . . 122.50(16) ?
C14 N1 C13 . . 115.12(15) ?
C10 N2 C16 . . 121.80(16) ?
C10 N2 C15 . . 122.36(16) ?
C16 N2 C15 . . 115.53(16) ?
C6 C1 C2 . . 115.43(17) ?
C6 C1 C7 . . 122.13(18) ?
C2 C1 C7 . . 122.35(18) ?
C3 C2 C1 . . 123.76(18) ?
C3 C2 Br1 . . 116.94(15) ?
C1 C2 Br1 . . 119.28(14) ?
C3 C2 H6A . . 118.1 ?
C1 C2 H6A . . 118.1 ?
Br1 C2 H6A . . 1.9 ?
C5 C6 C1 . . 122.72(19) ?
C5 C6 Br1A . . 130.4(3) ?
C1 C6 Br1A . . 106.2(2) ?
C5 C6 H6 . . 120.8(17) ?
C1 C6 H6 . . 116.4(17) ?
C6 Br1A C54 . 2_665 165.3(3) ?
C2 C3 C4 . . 119.83(18) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
N1 C4 C3 . . 121.47(17) ?
N1 C4 C5 . . 121.24(17) ?
C3 C4 C5 . . 117.28(17) ?
C6 C5 C4 . . 120.94(18) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C8 C7 C12 . . 115.94(17) ?
C8 C7 C1 . . 121.69(17) ?
C12 C7 C1 . . 122.34(17) ?
C9 C8 C7 . . 123.36(18) ?
C9 C8 Br2 . . 117.32(14) ?
C7 C8 Br2 . . 119.32(14) ?
C11 C12 C7 . . 122.45(18) ?
C11 C12 H12 . . 118.8 ?
C7 C12 H12 . . 118.8 ?
C8 C9 C10 . . 119.99(18) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
N2 C10 C11 . . 122.44(18) ?
N2 C10 C9 . . 120.21(17) ?
C11 C10 C9 . . 117.35(17) ?
C12 C11 C10 . . 120.81(18) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
N1 C13 C21 . . 113.35(15) ?
N1 C13 H13A . . 108.9 ?
C21 C13 H13A . . 108.9 ?
N1 C13 H13B . . 108.9 ?
C21 C13 H13B . . 108.9 ?
H13A C13 H13B . . 107.7 ?
N1 C14 C31 . . 115.15(16) ?
N1 C14 H14A . . 108.5 ?
C31 C14 H14A . . 108.5 ?
N1 C14 H14B . . 108.5 ?
C31 C14 H14B . . 108.5 ?
H14A C14 H14B . . 107.5 ?
N2 C15 C41 . . 114.73(16) ?
N2 C15 H15A . . 108.6 ?
C41 C15 H15A . . 108.6 ?
N2 C15 H15B . . 108.6 ?
C41 C15 H15B . . 108.6 ?
H15A C15 H15B . . 107.6 ?
N2 C16 C51 . . 115.24(17) ?
N2 C16 H16A . . 108.5 ?
C51 C16 H16A . . 108.5 ?
N2 C16 H16B . . 108.5 ?
C51 C16 H16B . . 108.5 ?
H16A C16 H16B . . 107.5 ?
C26 C21 C22 . . 118.61(19) ?
C26 C21 C13 . . 121.21(18) ?
C22 C21 C13 . . 120.18(19) ?
C23 C22 C21 . . 120.7(2) ?
C23 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
C24 C23 C22 . . 119.9(2) ?
C24 C23 H23 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
C23 C24 C25 . . 120.0(2) ?
C23 C24 H24 . . 120.0 ?
C25 C24 H24 . . 120.0 ?
C24 C25 C26 . . 120.2(2) ?
C24 C25 H25 . . 119.9 ?
C26 C25 H25 . . 119.9 ?
C25 C26 C21 . . 120.6(2) ?
C25 C26 H26 . . 119.7 ?
C21 C26 H26 . . 119.7 ?
C36 C31 C32 . . 118.81(18) ?
C36 C31 C14 . . 122.22(17) ?
C32 C31 C14 . . 118.95(18) ?
C33 C32 C31 . . 120.6(2) ?
C33 C32 H32 . . 119.7 ?
C31 C32 H32 . . 119.7 ?
C32 C33 C34 . . 120.2(2) ?
C32 C33 H33 . . 119.9 ?
C34 C33 H33 . . 119.9 ?
C35 C34 C33 . . 119.5(2) ?
C35 C34 H34 . . 120.3 ?
C33 C34 H34 . . 120.3 ?
C34 C35 C36 . . 120.25(19) ?
C34 C35 H35 . . 119.9 ?
C36 C35 H35 . . 119.9 ?
C31 C36 C35 . . 120.60(19) ?
C31 C36 H36 . . 119.7 ?
C35 C36 H36 . . 119.7 ?
C42 C41 C46 . . 118.76(19) ?
C42 C41 C15 . . 122.05(18) ?
C46 C41 C15 . . 119.17(18) ?
C43 C42 C41 . . 120.4(2) ?
C43 C42 H42 . . 119.8 ?
C41 C42 H42 . . 119.8 ?
C44 C43 C42 . . 120.3(2) ?
C44 C43 H43 . . 119.8 ?
C42 C43 H43 . . 119.8 ?
C43 C44 C45 . . 119.7(2) ?
C43 C44 H44 . . 120.2 ?
C45 C44 H44 . . 120.2 ?
C44 C45 C46 . . 120.2(2) ?
C44 C45 H45 . . 119.9 ?
C46 C45 H45 . . 119.9 ?
C45 C46 C41 . . 120.67(19) ?
C45 C46 H46 . . 119.7 ?
C41 C46 H46 . . 119.7 ?
C52 C51 C56 . . 118.4(2) ?
C52 C51 C16 . . 122.53(19) ?
C56 C51 C16 . . 119.1(2) ?
C51 C52 C53 . . 120.7(2) ?
C51 C52 H52 . . 119.7 ?
C53 C52 H52 . . 119.7 ?
C54 C53 C52 . . 120.4(2) ?
C54 C53 H53 . . 119.8 ?
C52 C53 H53 . . 119.8 ?
C53 C54 C55 . . 119.6(2) ?
C53 C54 Br1A . 2_665 94.7(2) ?
C55 C54 Br1A . 2_665 116.1(2) ?
C53 C54 H54 . . 120.2 ?
C55 C54 H54 . . 120.2 ?
Br1A C54 H54 2_665 . 58.8 ?
C54 C55 C56 . . 119.9(2) ?
C54 C55 H55 . . 120.0 ?
C56 C55 H55 . . 120.0 ?
C55 C56 C51 . . 121.0(2) ?
C55 C56 H56 . . 119.5 ?
C51 C56 H56 . . 119.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.2(3) ?
C7 C1 C2 C3 . . . . 176.93(18) ?
C6 C1 C2 Br1 . . . . -178.12(14) ?
C7 C1 C2 Br1 . . . . -1.4(3) ?
C2 C1 C6 C5 . . . . 1.5(3) ?
C7 C1 C6 C5 . . . . -175.27(18) ?
C2 C1 C6 Br1A . . . . -170.4(3) ?
C7 C1 C6 Br1A . . . . 12.9(3) ?
C5 C6 Br1A C54 . . . 2_665 -124.7(13) ?
C1 C6 Br1A C54 . . . 2_665 46.3(14) ?
C1 C2 C3 C4 . . . . -1.8(3) ?
Br1 C2 C3 C4 . . . . 176.57(14) ?
C14 N1 C4 C3 . . . . -176.67(17) ?
C13 N1 C4 C3 . . . . 18.4(3) ?
C14 N1 C4 C5 . . . . 2.1(3) ?
C13 N1 C4 C5 . . . . -162.85(17) ?
C2 C3 C4 N1 . . . . -179.54(17) ?
C2 C3 C4 C5 . . . . 1.7(3) ?
C1 C6 C5 C4 . . . . -1.6(3) ?
Br1A C6 C5 C4 . . . . 168.1(3) ?
N1 C4 C5 C6 . . . . -178.88(17) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
C6 C1 C7 C8 . . . . 85.6(3) ?
C2 C1 C7 C8 . . . . -90.9(2) ?
C6 C1 C7 C12 . . . . -96.7(2) ?
C2 C1 C7 C12 . . . . 86.7(3) ?
C12 C7 C8 C9 . . . . -0.2(3) ?
C1 C7 C8 C9 . . . . 177.58(18) ?
C12 C7 C8 Br2 . . . . -179.24(14) ?
C1 C7 C8 Br2 . . . . -1.5(3) ?
C8 C7 C12 C11 . . . . 1.9(3) ?
C1 C7 C12 C11 . . . . -175.83(19) ?
C7 C8 C9 C10 . . . . -2.6(3) ?
Br2 C8 C9 C10 . . . . 176.43(14) ?
C16 N2 C10 C11 . . . . -162.91(19) ?
C15 N2 C10 C11 . . . . 10.5(3) ?
C16 N2 C10 C9 . . . . 17.2(3) ?
C15 N2 C10 C9 . . . . -169.41(18) ?
C8 C9 C10 N2 . . . . -176.47(18) ?
C8 C9 C10 C11 . . . . 3.6(3) ?
C7 C12 C11 C10 . . . . -0.8(3) ?
N2 C10 C11 C12 . . . . 178.12(19) ?
C9 C10 C11 C12 . . . . -2.0(3) ?
C4 N1 C13 C21 . . . . -110.2(2) ?
C14 N1 C13 C21 . . . . 84.0(2) ?
C4 N1 C14 C31 . . . . -82.2(2) ?
C13 N1 C14 C31 . . . . 83.8(2) ?
C10 N2 C15 C41 . . . . -96.2(2) ?
C16 N2 C15 C41 . . . . 77.6(2) ?
C10 N2 C16 C51 . . . . -96.0(2) ?
C15 N2 C16 C51 . . . . 90.2(2) ?
N1 C13 C21 C26 . . . . 70.6(2) ?
N1 C13 C21 C22 . . . . -109.1(2) ?
C26 C21 C22 C23 . . . . -0.2(3) ?
C13 C21 C22 C23 . . . . 179.45(19) ?
C21 C22 C23 C24 . . . . 0.5(3) ?
C22 C23 C24 C25 . . . . -0.2(3) ?
C23 C24 C25 C26 . . . . -0.3(3) ?
C24 C25 C26 C21 . . . . 0.6(3) ?
C22 C21 C26 C25 . . . . -0.3(3) ?
C13 C21 C26 C25 . . . . -179.97(19) ?
N1 C14 C31 C36 . . . . -2.8(3) ?
N1 C14 C31 C32 . . . . 178.57(18) ?
C36 C31 C32 C33 . . . . -0.5(3) ?
C14 C31 C32 C33 . . . . 178.2(2) ?
C31 C32 C33 C34 . . . . -0.9(4) ?
C32 C33 C34 C35 . . . . 1.3(4) ?
C33 C34 C35 C36 . . . . -0.3(3) ?
C32 C31 C36 C35 . . . . 1.5(3) ?
C14 C31 C36 C35 . . . . -177.20(18) ?
C34 C35 C36 C31 . . . . -1.1(3) ?
N2 C15 C41 C42 . . . . 18.6(3) ?
N2 C15 C41 C46 . . . . -162.99(17) ?
C46 C41 C42 C43 . . . . 0.4(3) ?
C15 C41 C42 C43 . . . . 178.82(19) ?
C41 C42 C43 C44 . . . . -0.1(3) ?
C42 C43 C44 C45 . . . . -0.5(3) ?
C43 C44 C45 C46 . . . . 0.9(3) ?
C44 C45 C46 C41 . . . . -0.6(3) ?
C42 C41 C46 C45 . . . . 0.0(3) ?
C15 C41 C46 C45 . . . . -178.50(18) ?
N2 C16 C51 C52 . . . . 11.7(3) ?
N2 C16 C51 C56 . . . . -166.97(19) ?
C56 C51 C52 C53 . . . . -0.6(3) ?
C16 C51 C52 C53 . . . . -179.3(2) ?
C51 C52 C53 C54 . . . . -0.1(3) ?
C52 C53 C54 C55 . . . . 0.4(4) ?
C52 C53 C54 Br1A . . . 2_665 124.1(2) ?
C53 C54 C55 C56 . . . . 0.0(4) ?
Br1A C54 C55 C56 2_665 . . . -112.5(3) ?
C54 C55 C56 C51 . . . . -0.7(4) ?
C52 C51 C56 C55 . . . . 1.0(4) ?
C16 C51 C56 C55 . . . . 179.8(2) ?

####################################################################### 
# 
# 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_stu7779
_database_code_depnum_ccdc_archive 'CCDC 1052542'
_audit_update_record             
;
2015-03-06 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H39 N2 O P'
_chemical_formula_iupac          ?
_chemical_formula_weight         666.76

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7866(11)
_cell_length_b                   32.189(3)
_cell_length_c                   10.4301(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.194(6)
_cell_angle_gamma                90
_cell_volume                     3574.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9023
_cell_measurement_theta_min      2.7488
_cell_measurement_theta_max      64.9678
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.065
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408

_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            29470
_diffrn_reflns_av_R_equivalents  0.1840
_diffrn_reflns_av_unetI/netI     0.1197
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         57.90
_diffrn_reflns_theta_full        57.90
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             4911
_reflns_number_gt                3244
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2504
_refine_ls_R_factor_gt           0.1989
_refine_ls_wR_factor_gt          0.3847
_refine_ls_wR_factor_ref         0.4087
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_restrained_S_all      1.182
_refine_ls_number_reflns         4911
_refine_ls_number_parameters     561
_refine_ls_number_restraints     320
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+41.8516P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.151
_refine_diff_density_min         -0.364
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.5242(11) 0.2641(4) 0.5233(9) 0.055(3) Uani d . . . 1.0 . .
N N2 0.3330(10) 0.4731(3) 1.1473(9) 0.047(3) Uani d . . . 1.0 . .
O O1 0.1426(8) 0.3353(3) 0.8089(8) 0.057(3) Uani d . . . 1.0 . .
C C1 0.4898(12) 0.3584(4) 0.7958(10) 0.042(3) Uani d . . . 1.0 . .
C C2 0.3796(11) 0.3399(4) 0.7243(10) 0.045(3) Uani d . . . 1.0 . .
C C3 0.3922(12) 0.3081(4) 0.6336(11) 0.048(3) Uani d . . . 1.0 . .
H H3 0.3195 0.2958 0.5848 0.057 Uiso calc U . R 1.0 . .
C C4 0.5127(13) 0.2947(4) 0.6156(10) 0.050(4) Uani d . . . 1.0 . .
C C5 0.6167(13) 0.3128(4) 0.6897(11) 0.051(4) Uani d . . . 1.0 . .
H H5 0.6984 0.3035 0.6803 0.062 Uiso calc U . R 1.0 . .
C C6 0.6038(13) 0.3438(4) 0.7763(11) 0.049(3) Uani d . . . 1.0 . .
H H6 0.6774 0.3556 0.8248 0.059 Uiso calc U . R 1.0 . .
C C7 0.4558(12) 0.3903(4) 0.8862(10) 0.043(3) Uani d . . . 1.0 . .
C C8 0.3276(11) 0.3966(4) 0.8850(9) 0.038(3) Uani d . . . 1.0 . .
C C9 0.2843(13) 0.4245(4) 0.9685(10) 0.052(4) Uani d . . . 1.0 . .
H H9 0.1967 0.4288 0.9651 0.062 Uiso calc U . R 1.0 . .
C C10 0.3702(13) 0.4463(4) 1.0574(10) 0.041(3) Uani d . . . 1.0 . .
C C11 0.4989(12) 0.4409(4) 1.0558(11) 0.045(3) Uani d . . . 1.0 . .
H H11 0.5581 0.4566 1.1137 0.054 Uiso calc U . R 1.0 . .
C C12 0.5407(12) 0.4133(4) 0.9717(10) 0.046(3) Uani d . . . 1.0 . .
H H12 0.6283 0.4099 0.9722 0.055 Uiso calc U . R 1.0 . .
C C13 0.4130(13) 0.2473(4) 0.4463(12) 0.056(4) Uani d . . . 1.0 . .
H H13A 0.355 0.2383 0.5054 0.067 Uiso calc U . R 1.0 . .
H H13B 0.4369 0.2223 0.4007 0.067 Uiso calc U . R 1.0 . .
C C15 0.2035(14) 0.4845(4) 1.1461(12) 0.062(4) Uani d . . . 1.0 . .
H H15A 0.1892 0.4872 1.2371 0.074 Uiso calc U . R 1.0 . .
H H15B 0.1497 0.4616 1.1061 0.074 Uiso calc U . R 1.0 . .
C C16 0.4263(13) 0.4968(4) 1.2377(12) 0.054(4) Uani d . . . 1.0 . .
H H16A 0.3817 0.5178 1.2826 0.065 Uiso calc U . R 1.0 . .
H H16B 0.4822 0.5118 1.1869 0.065 Uiso calc U . R 1.0 . .
C C21 0.3423(14) 0.2770(4) 0.3452(11) 0.053(4) Uani d . . . 1.0 . .
C C22 0.2252(16) 0.2650(5) 0.2809(15) 0.070(5) Uani d . . . 1.0 . .
H H22 0.1878 0.24 0.3041 0.084 Uiso calc U . R 1.0 . .
C C23 0.1624(15) 0.2903(6) 0.1808(17) 0.084(5) Uani d . . . 1.0 . .
H H23 0.0818 0.2826 0.1364 0.101 Uiso calc U . R 1.0 . .
C C24 0.2206(17) 0.3272(5) 0.1473(17) 0.081(5) Uani d . . . 1.0 . .
H H24 0.1795 0.3446 0.0801 0.097 Uiso calc U . R 1.0 . .
C C25 0.3366(17) 0.3376(5) 0.2125(13) 0.068(4) Uani d . . . 1.0 . .
H H25 0.3755 0.3625 0.1906 0.082 Uiso calc U . R 1.0 . .
C C26 0.3980(14) 0.3124(4) 0.3095(12) 0.058(4) Uani d . . . 1.0 . .
H H26 0.4796 0.3198 0.3519 0.069 Uiso calc U . R 1.0 . .
C C14 0.6460(14) 0.2483(5) 0.5082(13) 0.077(5) Uani d . . D 1.0 . .
H H14A 0.7052 0.2719 0.5105 0.092 Uiso calc U P R 0.86(3) A 1
H H14B 0.6399 0.235 0.422 0.092 Uiso calc U P R 0.86(3) A 1
H H14C 0.6989 0.2717 0.4874 0.092 Uiso calc U P R 0.14(3) A 2
H H14D 0.6361 0.2288 0.4338 0.092 Uiso calc U P R 0.14(3) A 2
C C31 0.6991(17) 0.2167(5) 0.6134(16) 0.057(4) Uani d U P D 0.86(3) A 1
C C32 0.6358(19) 0.1822(5) 0.6369(15) 0.064(5) Uani d U P D 0.86(3) A 1
H H32 0.5572 0.1762 0.5849 0.077 Uiso calc U P R 0.86(3) A 1
C C33 0.6836(17) 0.1559(5) 0.7348(14) 0.064(5) Uani d U P D 0.86(3) A 1
H H33 0.6361 0.132 0.7492 0.077 Uiso calc U P R 0.86(3) A 1
C C34 0.7963(17) 0.1620(6) 0.8132(18) 0.080(6) Uani d U P D 0.86(3) A 1
H H34 0.8266 0.143 0.8806 0.096 Uiso calc U P R 0.86(3) A 1
C C35 0.864(2) 0.1963(6) 0.791(2) 0.088(6) Uani d U P D 0.86(3) A 1
H H35 0.9417 0.2016 0.8451 0.106 Uiso calc U P R 0.86(3) A 1
C C36 0.820(2) 0.2231(7) 0.693(2) 0.094(7) Uani d U P D 0.86(3) A 1
H H36 0.8698 0.2463 0.6768 0.112 Uiso calc U P R 0.86(3) A 1
C C31A 0.714(7) 0.226(2) 0.629(7) 0.057(12) Uani d U P D 0.14(3) A 2
C C32A 0.684(8) 0.1858(18) 0.651(7) 0.057(12) Uani d U P D 0.14(3) A 2
H H32A 0.6093 0.1737 0.6045 0.068 Uiso calc U P R 0.14(3) A 2
C C33A 0.762(9) 0.1631(19) 0.739(7) 0.074(10) Uani d U P D 0.14(3) A 2
H H33A 0.7393 0.1351 0.7536 0.089 Uiso calc U P R 0.14(3) A 2
C C34A 0.870(9) 0.178(3) 0.809(8) 0.088(13) Uani d U P D 0.14(3) A 2
H H34A 0.9233 0.1605 0.8675 0.106 Uiso calc U P R 0.14(3) A 2
C C35A 0.901(7) 0.218(3) 0.792(8) 0.089(13) Uani d U P D 0.14(3) A 2
H H35A 0.9734 0.23 0.8433 0.107 Uiso calc U P R 0.14(3) A 2
C C36A 0.829(7) 0.242(3) 0.700(7) 0.091(13) Uani d U P D 0.14(3) A 2
H H36A 0.8552 0.2695 0.6839 0.109 Uiso calc U P R 0.14(3) A 2
C C41 0.1606(10) 0.5243(4) 1.0752(11) 0.041(3) Uani d . . . 1.0 . .
C C42 0.1772(11) 0.5297(4) 0.9464(11) 0.047(3) Uani d . . . 1.0 . .
H H42 0.2121 0.508 0.9019 0.057 Uiso calc U . R 1.0 . .
C C43 0.1431(11) 0.5667(5) 0.8837(13) 0.059(4) Uani d . . . 1.0 . .
H H43 0.1531 0.5698 0.7953 0.07 Uiso calc U . R 1.0 . .
C C44 0.0952(12) 0.5988(5) 0.9456(14) 0.065(4) Uani d . . . 1.0 . .
H H44 0.0746 0.6241 0.9006 0.078 Uiso calc U . R 1.0 . .
C C45 0.0766(13) 0.5950(5) 1.0721(16) 0.068(4) Uani d . . . 1.0 . .
H H45 0.0427 0.6173 1.1151 0.082 Uiso calc U . R 1.0 . .
C C46 0.1092(11) 0.5568(4) 1.1372(13) 0.052(4) Uani d . . . 1.0 . .
H H46 0.0958 0.5535 1.2244 0.062 Uiso calc U . R 1.0 . .
C C51 0.5064(13) 0.4700(4) 1.3394(11) 0.052(4) Uani d . . . 1.0 . .
C C52 0.4542(13) 0.4357(4) 1.3914(11) 0.052(4) Uani d . . . 1.0 . .
H H52 0.3685 0.4287 1.3635 0.062 Uiso calc U . R 1.0 . .
C C53 0.5274(15) 0.4118(5) 1.4835(12) 0.064(4) Uani d . . . 1.0 . .
H H53 0.492 0.388 1.5178 0.077 Uiso calc U . R 1.0 . .
C C54 0.6480(16) 0.4215(5) 1.5256(11) 0.064(4) Uani d . . . 1.0 . .
H H54 0.6966 0.4051 1.591 0.077 Uiso calc U . R 1.0 . .
C C55 0.7015(14) 0.4553(6) 1.4740(13) 0.082(6) Uani d . . . 1.0 . .
H H55 0.7876 0.4618 1.5011 0.098 Uiso calc U . R 1.0 . .
C C56 0.6276(14) 0.4796(5) 1.3819(11) 0.065(4) Uani d . . . 1.0 . .
H H56 0.6632 0.5034 1.3481 0.078 Uiso calc U . R 1.0 . .
P P1 0.2398(3) 0.36274(12) 0.7658(3) 0.0537(10) Uani d . . D 1.0 . .
C C61 0.1833(16) 0.3955(6) 0.6315(14) 0.044(4) Uani d U P D 0.743(15) B 1
C C62 0.1696(15) 0.3793(6) 0.5048(14) 0.069(6) Uani d U P D 0.743(15) B 1
H H62 0.2039 0.3528 0.4908 0.083 Uiso calc U P R 0.743(15) B 1
C C63 0.1055(16) 0.4017(5) 0.3980(17) 0.068(6) Uani d U P D 0.743(15) B 1
H H63 0.0923 0.3902 0.3132 0.082 Uiso calc U P R 0.743(15) B 1
C C64 0.0618(19) 0.4418(6) 0.4213(16) 0.059(5) Uani d U P D 0.743(15) B 1
H H64 0.0284 0.4592 0.3505 0.071 Uiso calc U P R 0.743(15) B 1
C C65 0.068(2) 0.4562(7) 0.5496(16) 0.087(7) Uani d U P D 0.743(15) B 1
H H65 0.0294 0.4816 0.5683 0.104 Uiso calc U P R 0.743(15) B 1
C C66 0.1328(18) 0.4310(6) 0.6495(18) 0.068(6) Uani d U P D 0.743(15) B 1
H H66 0.1399 0.4409 0.7362 0.082 Uiso calc U P R 0.743(15) B 1
C C61A 0.159(3) 0.3918(13) 0.635(4) 0.043(10) Uani d U P D 0.257(15) B 2
C C62A 0.227(3) 0.4244(11) 0.590(3) 0.045(13) Uani d U P D 0.257(15) B 2
H H62A 0.3085 0.4311 0.6342 0.054 Uiso calc U P R 0.257(15) B 2
C C63A 0.174(4) 0.4473(13) 0.479(4) 0.09(2) Uani d U P D 0.257(15) B 2
H H63A 0.2171 0.4701 0.4486 0.11 Uiso calc U P R 0.257(15) B 2
C C64A 0.055(5) 0.4347(16) 0.416(4) 0.057(10) Uani d U P D 0.257(15) B 2
H H64A 0.0196 0.4477 0.3366 0.068 Uiso calc U P R 0.257(15) B 2
C C65A -0.013(5) 0.4033(18) 0.468(5) 0.15(4) Uani d U P D 0.257(15) B 2
H H65A -0.0965 0.3964 0.4286 0.178 Uiso calc U P R 0.257(15) B 2
C C66A 0.047(3) 0.3823(14) 0.580(4) 0.077(19) Uani d U P D 0.257(15) B 2
H H66A 0.0034 0.3606 0.6154 0.092 Uiso calc U P R 0.257(15) B 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C4 . 1.398(16) ?
N1 C13 . 1.438(16) ?
N1 C14 . 1.439(17) ?
N2 C10 . 1.379(15) ?
N2 C15 . 1.443(17) ?
N2 C16 . 1.477(15) ?
O1 P1 . 1.495(9) ?
C1 C6 . 1.362(17) ?
C1 C2 . 1.429(17) ?
C1 C7 . 1.478(17) ?
C2 C3 . 1.414(17) ?
C2 P1 . 1.792(12) ?
C3 C4 . 1.410(17) ?
C4 C5 . 1.384(18) ?
C5 C6 . 1.367(17) ?
C7 C12 . 1.385(16) ?
C7 C8 . 1.396(16) ?
C8 C9 . 1.384(16) ?
C8 P1 . 1.803(11) ?
C9 C10 . 1.392(17) ?
C10 C11 . 1.401(17) ?
C11 C12 . 1.375(17) ?
C13 C21 . 1.532(18) ?
C15 C41 . 1.513(18) ?
C16 C51 . 1.524(18) ?
C21 C26 . 1.368(18) ?
C21 C22 . 1.39(2) ?
C22 C23 . 1.41(2) ?
C23 C24 . 1.41(2) ?
C24 C25 . 1.37(2) ?
C25 C26 . 1.379(19) ?
C14 C31A . 1.53(3) ?
C14 C31 . 1.54(2) ?
C31 C32 . 1.347(14) ?
C31 C36 . 1.44(2) ?
C32 C33 . 1.364(14) ?
C33 C34 . 1.367(14) ?
C34 C35 . 1.359(15) ?
C35 C36 . 1.366(15) ?
C31A C32A . 1.360(17) ?
C31A C36A . 1.44(3) ?
C32A C33A . 1.360(17) ?
C33A C34A . 1.361(17) ?
C34A C35A . 1.362(17) ?
C35A C36A . 1.362(17) ?
C41 C46 . 1.391(17) ?
C41 C42 . 1.394(16) ?
C42 C43 . 1.378(19) ?
C43 C44 . 1.36(2) ?
C44 C45 . 1.372(19) ?
C45 C46 . 1.420(19) ?
C51 C56 . 1.348(18) ?
C51 C52 . 1.389(18) ?
C52 C53 . 1.377(19) ?
C53 C54 . 1.342(19) ?
C54 C55 . 1.38(2) ?
C55 C56 . 1.39(2) ?
P1 C61A . 1.765(19) ?
P1 C61 . 1.780(14) ?
C61 C66 . 1.29(3) ?
C61 C62 . 1.406(15) ?
C62 C63 . 1.412(14) ?
C63 C64 . 1.409(15) ?
C64 C65 . 1.407(15) ?
C65 C66 . 1.416(15) ?
C61A C66A . 1.29(3) ?
C61A C62A . 1.408(17) ?
C62A C63A . 1.412(17) ?
C63A C64A . 1.408(17) ?
C64A C65A . 1.408(17) ?
C65A C66A . 1.415(17) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 C13 . . 119.5(11) ?
C4 N1 C14 . . 120.5(12) ?
C13 N1 C14 . . 120.0(11) ?
C10 N2 C15 . . 122.7(10) ?
C10 N2 C16 . . 120.9(11) ?
C15 N2 C16 . . 115.7(10) ?
C6 C1 C2 . . 118.2(12) ?
C6 C1 C7 . . 131.1(12) ?
C2 C1 C7 . . 110.7(11) ?
C3 C2 C1 . . 119.4(11) ?
C3 C2 P1 . . 129.3(10) ?
C1 C2 P1 . . 111.3(9) ?
C4 C3 C2 . . 119.9(12) ?
C5 C4 N1 . . 121.9(12) ?
C5 C4 C3 . . 118.6(12) ?
N1 C4 C3 . . 119.5(12) ?
C6 C5 C4 . . 121.1(13) ?
C1 C6 C5 . . 122.8(13) ?
C12 C7 C8 . . 118.7(11) ?
C12 C7 C1 . . 125.1(12) ?
C8 C7 C1 . . 116.1(11) ?
C9 C8 C7 . . 121.4(11) ?
C9 C8 P1 . . 129.3(10) ?
C7 C8 P1 . . 109.2(8) ?
C8 C9 C10 . . 119.4(12) ?
N2 C10 C9 . . 122.2(12) ?
N2 C10 C11 . . 118.9(11) ?
C9 C10 C11 . . 119.0(11) ?
C12 C11 C10 . . 121.0(11) ?
C11 C12 C7 . . 120.4(12) ?
N1 C13 C21 . . 115.4(12) ?
N2 C15 C41 . . 116.2(10) ?
N2 C16 C51 . . 113.9(11) ?
C26 C21 C22 . . 120.4(13) ?
C26 C21 C13 . . 121.0(14) ?
C22 C21 C13 . . 118.3(13) ?
C21 C22 C23 . . 119.4(15) ?
C22 C23 C24 . . 119.3(17) ?
C25 C24 C23 . . 119.3(16) ?
C24 C25 C26 . . 121.0(15) ?
C21 C26 C25 . . 120.6(14) ?
N1 C14 C31A . . 113.(4) ?
N1 C14 C31 . . 113.4(12) ?
C32 C31 C36 . . 116.8(16) ?
C32 C31 C14 . . 122.2(15) ?
C36 C31 C14 . . 121.1(15) ?
C31 C32 C33 . . 120.4(17) ?
C32 C33 C34 . . 123.5(18) ?
C35 C34 C33 . . 117.7(19) ?
C34 C35 C36 . . 121.(2) ?
C35 C36 C31 . . 121.(2) ?
C32A C31A C36A . . 118.(3) ?
C32A C31A C14 . . 119.(3) ?
C36A C31A C14 . . 121.(3) ?
C33A C32A C31A . . 119.(3) ?
C32A C33A C34A . . 124.(3) ?
C33A C34A C35A . . 118.(3) ?
C34A C35A C36A . . 120.(3) ?
C35A C36A C31A . . 121.(3) ?
C46 C41 C42 . . 118.4(13) ?
C46 C41 C15 . . 121.5(11) ?
C42 C41 C15 . . 120.0(11) ?
C43 C42 C41 . . 120.0(13) ?
C44 C43 C42 . . 121.4(13) ?
C43 C44 C45 . . 120.9(15) ?
C44 C45 C46 . . 118.3(14) ?
C41 C46 C45 . . 121.0(12) ?
C56 C51 C52 . . 119.1(13) ?
C56 C51 C16 . . 120.8(13) ?
C52 C51 C16 . . 120.1(13) ?
C53 C52 C51 . . 119.5(13) ?
C54 C53 C52 . . 121.1(15) ?
C53 C54 C55 . . 120.0(14) ?
C54 C55 C56 . . 119.0(14) ?
C51 C56 C55 . . 121.2(15) ?
O1 P1 C61A . . 105.0(12) ?
O1 P1 C61 . . 114.7(7) ?
O1 P1 C2 . . 119.2(6) ?
C61A P1 C2 . . 111.4(15) ?
C61 P1 C2 . . 104.4(7) ?
O1 P1 C8 . . 117.8(5) ?
C61A P1 C8 . . 110.7(16) ?
C61 P1 C8 . . 105.2(8) ?
C2 P1 C8 . . 92.6(6) ?
C66 C61 C62 . . 118.7(15) ?
C66 C61 P1 . . 120.6(13) ?
C62 C61 P1 . . 119.5(14) ?
C61 C62 C63 . . 121.1(16) ?
C64 C63 C62 . . 117.9(16) ?
C65 C64 C63 . . 120.0(16) ?
C64 C65 C66 . . 117.0(18) ?
C61 C66 C65 . . 124.8(19) ?
C66A C61A C62A . . 122.(2) ?
C66A C61A P1 . . 122.(2) ?
C62A C61A P1 . . 116.(2) ?
C61A C62A C63A . . 120.(2) ?
C64A C63A C62A . . 117.(3) ?
C65A C64A C63A . . 121.(3) ?
C64A C65A C66A . . 117.(3) ?
C61A C66A C65A . . 122.(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.9(17) ?
C7 C1 C2 C3 . . . . -179.1(10) ?
C6 C1 C2 P1 . . . . 178.9(9) ?
C7 C1 C2 P1 . . . . 1.6(12) ?
C1 C2 C3 C4 . . . . 0.7(17) ?
P1 C2 C3 C4 . . . . 179.8(9) ?
C13 N1 C4 C5 . . . . -178.1(12) ?
C14 N1 C4 C5 . . . . 4.0(19) ?
C13 N1 C4 C3 . . . . 1.2(17) ?
C14 N1 C4 C3 . . . . -176.6(12) ?
C2 C3 C4 C5 . . . . 1.1(17) ?
C2 C3 C4 N1 . . . . -178.3(11) ?
N1 C4 C5 C6 . . . . 177.6(11) ?
C3 C4 C5 C6 . . . . -1.8(18) ?
C2 C1 C6 C5 . . . . 1.2(18) ?
C7 C1 C6 C5 . . . . 177.9(12) ?
C4 C5 C6 C1 . . . . 0.6(19) ?
C6 C1 C7 C12 . . . . 2.(2) ?
C2 C1 C7 C12 . . . . 178.3(11) ?
C6 C1 C7 C8 . . . . -177.2(12) ?
C2 C1 C7 C8 . . . . -0.4(14) ?
C12 C7 C8 C9 . . . . -1.1(18) ?
C1 C7 C8 C9 . . . . 177.7(11) ?
C12 C7 C8 P1 . . . . -179.8(9) ?
C1 C7 C8 P1 . . . . -1.1(13) ?
C7 C8 C9 C10 . . . . -1.3(18) ?
P1 C8 C9 C10 . . . . 177.2(9) ?
C15 N2 C10 C9 . . . . -8.0(18) ?
C16 N2 C10 C9 . . . . -178.1(11) ?
C15 N2 C10 C11 . . . . 172.1(11) ?
C16 N2 C10 C11 . . . . 2.0(17) ?
C8 C9 C10 N2 . . . . -176.8(11) ?
C8 C9 C10 C11 . . . . 3.1(18) ?
N2 C10 C11 C12 . . . . 177.2(11) ?
C9 C10 C11 C12 . . . . -2.6(18) ?
C10 C11 C12 C7 . . . . 0.3(18) ?
C8 C7 C12 C11 . . . . 1.6(17) ?
C1 C7 C12 C11 . . . . -177.1(11) ?
C4 N1 C13 C21 . . . . 70.2(14) ?
C14 N1 C13 C21 . . . . -111.9(14) ?
C10 N2 C15 C41 . . . . -94.3(14) ?
C16 N2 C15 C41 . . . . 76.3(13) ?
C10 N2 C16 C51 . . . . -68.9(15) ?
C15 N2 C16 C51 . . . . 120.3(12) ?
N1 C13 C21 C26 . . . . 15.7(17) ?
N1 C13 C21 C22 . . . . -170.8(11) ?
C26 C21 C22 C23 . . . . -2.(2) ?
C13 C21 C22 C23 . . . . -175.3(13) ?
C21 C22 C23 C24 . . . . 1.(2) ?
C22 C23 C24 C25 . . . . 0.(2) ?
C23 C24 C25 C26 . . . . 1.(2) ?
C22 C21 C26 C25 . . . . 2.(2) ?
C13 C21 C26 C25 . . . . 175.8(12) ?
C24 C25 C26 C21 . . . . -2.(2) ?
C4 N1 C14 C31A . . . . 63.(3) ?
C13 N1 C14 C31A . . . . -114.(3) ?
C4 N1 C14 C31 . . . . 78.1(17) ?
C13 N1 C14 C31 . . . . -99.7(15) ?
N1 C14 C31 C32 . . . . 55.6(19) ?
N1 C14 C31 C36 . . . . -123.8(17) ?
C36 C31 C32 C33 . . . . 2.2(16) ?
C14 C31 C32 C33 . . . . -177.2(17) ?
C31 C32 C33 C34 . . . . -0.6(17) ?
C32 C33 C34 C35 . . . . 0.(3) ?
C33 C34 C35 C36 . . . . -1.(3) ?
C34 C35 C36 C31 . . . . 3.(3) ?
C32 C31 C36 C35 . . . . -3.(3) ?
C14 C31 C36 C35 . . . . 176.(2) ?
N1 C14 C31A C32A . . . . 81.(6) ?
N1 C14 C31A C36A . . . . -116.(6) ?
C36A C31A C32A C33A . . . . 1.(3) ?
C14 C31A C32A C33A . . . . 165.(8) ?
C31A C32A C33A C34A . . . . 0.(3) ?
C32A C33A C34A C35A . . . . 2.(7) ?
C33A C34A C35A C36A . . . . -5.(9) ?
C34A C35A C36A C31A . . . . 5.(9) ?
C32A C31A C36A C35A . . . . -4.(6) ?
C14 C31A C36A C35A . . . . -167.(9) ?
N2 C15 C41 C46 . . . . -122.8(12) ?
N2 C15 C41 C42 . . . . 54.3(16) ?
C46 C41 C42 C43 . . . . 0.0(17) ?
C15 C41 C42 C43 . . . . -177.2(12) ?
C41 C42 C43 C44 . . . . 1.(2) ?
C42 C43 C44 C45 . . . . -2.(2) ?
C43 C44 C45 C46 . . . . 0.(2) ?
C42 C41 C46 C45 . . . . -1.1(18) ?
C15 C41 C46 C45 . . . . 176.0(12) ?
C44 C45 C46 C41 . . . . 1.(2) ?
N2 C16 C51 C56 . . . . 145.5(12) ?
N2 C16 C51 C52 . . . . -35.7(17) ?
C56 C51 C52 C53 . . . . -1.0(19) ?
C16 C51 C52 C53 . . . . -179.8(12) ?
C51 C52 C53 C54 . . . . 1.(2) ?
C52 C53 C54 C55 . . . . -2.(2) ?
C53 C54 C55 C56 . . . . 2.(2) ?
C52 C51 C56 C55 . . . . 1.(2) ?
C16 C51 C56 C55 . . . . -179.7(13) ?
C54 C55 C56 C51 . . . . -2.(2) ?
C3 C2 P1 O1 . . . . 54.9(13) ?
C1 C2 P1 O1 . . . . -126.0(9) ?
C3 C2 P1 C61A . . . . -68.(2) ?
C1 C2 P1 C61A . . . . 111.5(18) ?
C3 C2 P1 C61 . . . . -74.7(13) ?
C1 C2 P1 C61 . . . . 104.4(10) ?
C3 C2 P1 C8 . . . . 179.0(12) ?
C1 C2 P1 C8 . . . . -1.9(9) ?
C9 C8 P1 O1 . . . . -51.8(13) ?
C7 C8 P1 O1 . . . . 126.8(8) ?
C9 C8 P1 C61A . . . . 69.0(19) ?
C7 C8 P1 C61A . . . . -112.3(16) ?
C9 C8 P1 C61 . . . . 77.4(13) ?
C7 C8 P1 C61 . . . . -104.0(10) ?
C9 C8 P1 C2 . . . . -177.0(12) ?
C7 C8 P1 C2 . . . . 1.7(9) ?
O1 P1 C61 C66 . . . . 85.2(17) ?
C2 P1 C61 C66 . . . . -142.6(16) ?
C8 P1 C61 C66 . . . . -45.8(17) ?
O1 P1 C61 C62 . . . . -81.6(12) ?
C2 P1 C61 C62 . . . . 50.7(13) ?
C8 P1 C61 C62 . . . . 147.4(11) ?
C66 C61 C62 C63 . . . . 2.0(18) ?
P1 C61 C62 C63 . . . . 169.0(14) ?
C61 C62 C63 C64 . . . . 3.4(17) ?
C62 C63 C64 C65 . . . . -8.(3) ?
C63 C64 C65 C66 . . . . 8.(3) ?
C62 C61 C66 C65 . . . . -3.(3) ?
P1 C61 C66 C65 . . . . -169.5(17) ?
C64 C65 C66 C61 . . . . -2.(3) ?
O1 P1 C61A C66A . . . . -13.(4) ?
C2 P1 C61A C66A . . . . 117.(3) ?
C8 P1 C61A C66A . . . . -141.(3) ?
O1 P1 C61A C62A . . . . 171.(2) ?
C2 P1 C61A C62A . . . . -59.(3) ?
C8 P1 C61A C62A . . . . 43.(3) ?
C66A C61A C62A C63A . . . . -1.(3) ?
P1 C61A C62A C63A . . . . 175.(4) ?
C61A C62A C63A C64A . . . . -2.(2) ?
C62A C63A C64A C65A . . . . 6.(5) ?
C63A C64A C65A C66A . . . . -5.(7) ?
C62A C61A C66A C65A . . . . 2.(6) ?
P1 C61A C66A C65A . . . . -174.(4) ?
C64A C65A C66A C61A . . . . 1.(7) ?

####################################################################### 
# 
# 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_stu8138
_database_code_depnum_ccdc_archive 'CCDC 1425330'
_audit_update_record             
;
2015-09-17 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H66 N2 O2 P2'
_chemical_formula_iupac          ?
_chemical_formula_weight         861.04

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   29.5733(17)
_cell_length_b                   8.8680(6)
_cell_length_c                   20.0015(11)
_cell_angle_alpha                90
_cell_angle_beta                 109.810(2)
_cell_angle_gamma                90
_cell_volume                     4935.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8394
_cell_measurement_theta_min      2.4105
_cell_measurement_theta_max      25.2609
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.063
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848

_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            37687
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
A badly disordered half acetonitrile molecule was found in the asymmetrical
unit and could not be satisfactorily refined. The program SQUEEZE (A. L. 
Spek J. Appl. Cryst., 2003, 36, 7-13) was therefore used to remove 
mathematically the effect of the solvent. 
The quoted formula and derived parameters are not included the squeezed
solvent molecule.

The C6H13 group is disordered over two positions. Several restraints (SADI,
SAME, ISOR and SIMU) were used in order to improve refinement stability.
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.119 0.250 77.8 19.9
2 0.000 -0.120 0.750 77.8 19.9
3 0.500 0.380 0.750 77.8 19.9
4 0.500 0.619 0.250 77.8 19.9

_reflns_number_total             4351
_reflns_number_gt                3206
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1627
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_number_reflns         4351
_refine_ls_number_parameters     335
_refine_ls_number_restraints     167
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0727P)²+11.4386P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.358
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.39300(8) 0.2526(3) 0.29185(12) 0.0233(5) Uani d . . . 1.0 . .
O O1 0.52801(7) 0.3594(2) 0.59667(11) 0.0263(5) Uani d . . . 1.0 . .
P P1 0.53771(3) 0.24597(9) 0.54887(4) 0.0199(2) Uani d . . . 1.0 . .
C C1 0.48717(10) 0.1934(3) 0.46751(14) 0.0177(6) Uani d . . . 1.0 . .
C C2 0.45625(9) 0.2678(3) 0.40864(14) 0.0186(6) Uani d . . . 1.0 . .
H H2 0.457 0.3746 0.4056 0.022 Uiso calc U . R 1.0 . .
C C3 0.42315(10) 0.1820(3) 0.35259(14) 0.0187(6) Uani d . . . 1.0 . .
C C4 0.42117(9) 0.0216(3) 0.35830(14) 0.0169(6) Uani d . . . 1.0 . .
H H4 0.3991 -0.0354 0.3213 0.02 Uiso calc U . R 1.0 . .
C C5 0.45166(10) -0.0503(3) 0.41820(15) 0.0180(6) Uani d . . . 1.0 . .
C C6 0.48377(10) 0.0375(3) 0.46997(14) 0.0171(6) Uani d . . . 1.0 . .
C C7 0.39439(10) 0.4132(3) 0.27903(15) 0.0225(7) Uani d . . . 1.0 . .
H H7A 0.394 0.4285 0.2298 0.027 Uiso calc U . R 1.0 . .
H H7B 0.4251 0.4542 0.3115 0.027 Uiso calc U . R 1.0 . .
C C8 0.35931(10) 0.1661(4) 0.23498(15) 0.0253(7) Uani d . . . 1.0 . .
H H8A 0.3356 0.2365 0.2034 0.03 Uiso calc U . R 1.0 . .
H H8B 0.3416 0.0968 0.2561 0.03 Uiso calc U . R 1.0 . .
C C11 0.58731(11) 0.2922(4) 0.51908(17) 0.0281(7) Uani d . . . 1.0 . .
H H11A 0.6165 0.3079 0.5611 0.034 Uiso calc U . R 1.0 . .
H H11B 0.5934 0.2056 0.4921 0.034 Uiso calc U . R 1.0 . .
C C12 0.57852(12) 0.4329(4) 0.47231(18) 0.0316(8) Uani d U . D 1.0 . .
H H12A 0.5813 0.5234 0.5024 0.038 Uiso calc U P R 0.805(6) A 1
H H12B 0.5454 0.4298 0.4377 0.038 Uiso calc U P R 0.805(6) A 1
H H12C 0.5568 0.3996 0.4251 0.038 Uiso calc U P R 0.195(6) A 2
H H12D 0.5592 0.5007 0.4913 0.038 Uiso calc U P R 0.195(6) A 2
C C13 0.61410(13) 0.4458(5) 0.43203(19) 0.0227(10) Uani d U P D 0.805(6) A 1
H H13A 0.6115 0.3537 0.403 0.027 Uiso calc U P R 0.805(6) A 1
H H13B 0.6046 0.5325 0.399 0.027 Uiso calc U P R 0.805(6) A 1
C C14 0.66667(14) 0.4661(5) 0.4789(3) 0.0225(10) Uani d U P D 0.805(6) A 1
H H14A 0.6701 0.5644 0.5037 0.027 Uiso calc U P R 0.805(6) A 1
H H14B 0.6752 0.3861 0.5156 0.027 Uiso calc U P R 0.805(6) A 1
C C15 0.70206(14) 0.4605(6) 0.4383(2) 0.0284(10) Uani d U P D 0.805(6) A 1
H H15A 0.6986 0.3627 0.4131 0.034 Uiso calc U P R 0.805(6) A 1
H H15B 0.6941 0.5415 0.4021 0.034 Uiso calc U P R 0.805(6) A 1
C C16 0.75412(13) 0.4791(5) 0.4870(2) 0.0316(11) Uani d U P D 0.805(6) A 1
H H16A 0.7584 0.5822 0.5072 0.038 Uiso calc U P R 0.805(6) A 1
H H16B 0.7605 0.4072 0.527 0.038 Uiso calc U P R 0.805(6) A 1
C C17 0.79101(15) 0.4535(5) 0.4505(2) 0.0344(11) Uani d U P D 0.805(6) A 1
H H17A 0.8235 0.4533 0.4868 0.041 Uiso calc U P R 0.805(6) A 1
H H17B 0.7855 0.3529 0.4277 0.041 Uiso calc U P R 0.805(6) A 1
C C18 0.7893(3) 0.5709(7) 0.3949(3) 0.0530(16) Uani d U P D 0.805(6) A 1
H H18A 0.8139 0.548 0.3735 0.08 Uiso calc U P R 0.805(6) A 1
H H18B 0.7575 0.5702 0.3579 0.08 Uiso calc U P R 0.805(6) A 1
H H18C 0.7956 0.6707 0.4172 0.08 Uiso calc U P R 0.805(6) A 1
C C13A 0.6139(7) 0.531(2) 0.4575(16) 0.073(8) Uani d U P D 0.195(6) A 2
H H13C 0.6258 0.606 0.4962 0.088 Uiso calc U P R 0.195(6) A 2
H H13D 0.5982 0.5868 0.4127 0.088 Uiso calc U P R 0.195(6) A 2
C C14A 0.6561(7) 0.443(2) 0.4510(14) 0.042(6) Uani d U P D 0.195(6) A 2
H H14C 0.6719 0.387 0.4957 0.05 Uiso calc U P R 0.195(6) A 2
H H14D 0.6442 0.3682 0.4121 0.05 Uiso calc U P R 0.195(6) A 2
C C15A 0.6920(6) 0.544(2) 0.4361(12) 0.045(5) Uani d U P D 0.195(6) A 2
H H15C 0.675 0.5978 0.3912 0.054 Uiso calc U P R 0.195(6) A 2
H H15D 0.7012 0.6215 0.4741 0.054 Uiso calc U P R 0.195(6) A 2
C C16A 0.7374(7) 0.485(2) 0.4298(14) 0.059(6) Uani d U P D 0.195(6) A 2
H H16C 0.7295 0.4167 0.3883 0.071 Uiso calc U P R 0.195(6) A 2
H H16D 0.7544 0.4248 0.4727 0.071 Uiso calc U P R 0.195(6) A 2
C C17A 0.7707(8) 0.609(3) 0.4215(17) 0.079(8) Uani d U P D 0.195(6) A 2
H H17C 0.7535 0.6728 0.38 0.095 Uiso calc U P R 0.195(6) A 2
H H17D 0.7806 0.6739 0.4643 0.095 Uiso calc U P R 0.195(6) A 2
C C18A 0.8146(9) 0.540(3) 0.4113(15) 0.058(7) Uani d U P D 0.195(6) A 2
H H18D 0.8359 0.6204 0.4059 0.088 Uiso calc U P R 0.195(6) A 2
H H18E 0.8317 0.4781 0.4527 0.088 Uiso calc U P R 0.195(6) A 2
H H18F 0.8047 0.4769 0.3685 0.088 Uiso calc U P R 0.195(6) A 2
C C21 0.35337(10) 0.5024(3) 0.28906(15) 0.0214(6) Uani d . . . 1.0 . .
C C22 0.32306(11) 0.4423(4) 0.32162(17) 0.0311(8) Uani d . . . 1.0 . .
H H22 0.3276 0.3415 0.3387 0.037 Uiso calc U . R 1.0 . .
C C23 0.28572(12) 0.5288(5) 0.32951(19) 0.0405(9) Uani d . . . 1.0 . .
H H23 0.265 0.4868 0.352 0.049 Uiso calc U . R 1.0 . .
C C24 0.27888(12) 0.6740(4) 0.3049(2) 0.0434(10) Uani d . . . 1.0 . .
H H24 0.2532 0.732 0.3098 0.052 Uiso calc U . R 1.0 . .
C C25 0.30905(12) 0.7362(4) 0.2732(2) 0.0398(9) Uani d . . . 1.0 . .
H H25 0.3045 0.8374 0.2568 0.048 Uiso calc U . R 1.0 . .
C C26 0.34615(11) 0.6510(4) 0.26523(17) 0.0280(7) Uani d . . . 1.0 . .
H H26 0.3669 0.6945 0.2432 0.034 Uiso calc U . R 1.0 . .
C C31 0.38156(10) 0.0739(4) 0.18985(15) 0.0240(7) Uani d . . . 1.0 . .
C C32 0.35514(12) -0.0392(4) 0.14547(17) 0.0353(8) Uani d . . . 1.0 . .
H H32 0.3235 -0.0602 0.1447 0.042 Uiso calc U . R 1.0 . .
C C33 0.37407(14) -0.1223(5) 0.10217(19) 0.0471(10) Uani d . . . 1.0 . .
H H33 0.3554 -0.1992 0.0723 0.057 Uiso calc U . R 1.0 . .
C C34 0.41990(14) -0.0932(5) 0.10252(19) 0.0459(10) Uani d . . . 1.0 . .
H H34 0.433 -0.1497 0.0731 0.055 Uiso calc U . R 1.0 . .
C C35 0.44674(13) 0.0196(4) 0.14630(18) 0.0392(9) Uani d . . . 1.0 . .
H H35 0.4783 0.0409 0.1465 0.047 Uiso calc U . R 1.0 . .
C C36 0.42771(11) 0.1021(4) 0.19022(17) 0.0294(7) Uani d . . . 1.0 . .
H H36 0.4466 0.178 0.2205 0.035 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C3 . 1.389(4) ?
N1 C7 . 1.450(4) ?
N1 C8 . 1.452(4) ?
O1 P1 . 1.482(2) ?
P1 C11 . 1.807(3) ?
P1 C5 5_656 1.845(3) ?
P1 C1 . 1.858(3) ?
C1 C6 . 1.388(4) ?
C1 C2 . 1.389(4) ?
C2 C3 . 1.432(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.430(4) ?
C4 C5 . 1.387(4) ?
C4 H4 . 0.95 ?
C5 C6 . 1.383(4) ?
C5 P1 5_656 1.845(3) ?
C6 C6 5_656 1.423(5) ?
C7 C21 . 1.517(4) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C31 . 1.523(4) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C11 C12 . 1.528(4) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13A . 1.468(13) ?
C12 C13 . 1.531(5) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C12 H12C . 0.99 ?
C12 H12D . 0.99 ?
C13 C14 . 1.530(5) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.529(5) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.527(5) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C17 . 1.522(5) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C18 . 1.512(6) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C13A C14A . 1.515(14) ?
C13A H13C . 0.99 ?
C13A H13D . 0.99 ?
C14A C15A . 1.498(14) ?
C14A H14C . 0.99 ?
C14A H14D . 0.99 ?
C15A C16A . 1.486(14) ?
C15A H15C . 0.99 ?
C15A H15D . 0.99 ?
C16A C17A . 1.524(14) ?
C16A H16C . 0.99 ?
C16A H16D . 0.99 ?
C17A C18A . 1.511(14) ?
C17A H17C . 0.99 ?
C17A H17D . 0.99 ?
C18A H18D . 0.98 ?
C18A H18E . 0.98 ?
C18A H18F . 0.98 ?
C21 C22 . 1.381(4) ?
C21 C26 . 1.393(4) ?
C22 C23 . 1.397(5) ?
C22 H22 . 0.95 ?
C23 C24 . 1.369(5) ?
C23 H23 . 0.95 ?
C24 C25 . 1.373(5) ?
C24 H24 . 0.95 ?
C25 C26 . 1.385(5) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C31 C36 . 1.385(4) ?
C31 C32 . 1.391(5) ?
C32 C33 . 1.391(5) ?
C32 H32 . 0.95 ?
C33 C34 . 1.377(5) ?
C33 H33 . 0.95 ?
C34 C35 . 1.387(5) ?
C34 H34 . 0.95 ?
C35 C36 . 1.400(5) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 C7 . . 123.3(2) ?
C3 N1 C8 . . 120.9(2) ?
C7 N1 C8 . . 115.7(2) ?
O1 P1 C11 . . 114.54(14) ?
O1 P1 C5 . 5_656 117.08(12) ?
C11 P1 C5 . 5_656 105.78(14) ?
O1 P1 C1 . . 117.48(12) ?
C11 P1 C1 . . 105.67(13) ?
C5 P1 C1 5_656 . 93.77(13) ?
C6 C1 C2 . . 117.9(3) ?
C6 C1 P1 . . 105.4(2) ?
C2 C1 P1 . . 136.6(2) ?
C1 C2 C3 . . 119.4(3) ?
C1 C2 H2 . . 120.3 ?
C3 C2 H2 . . 120.3 ?
N1 C3 C4 . . 119.1(3) ?
N1 C3 C2 . . 120.7(3) ?
C4 C3 C2 . . 120.1(3) ?
C5 C4 C3 . . 119.6(3) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C6 C5 C4 . . 117.9(3) ?
C6 C5 P1 . 5_656 105.7(2) ?
C4 C5 P1 . 5_656 136.3(2) ?
C5 C6 C1 . . 125.0(3) ?
C5 C6 C6 . 5_656 117.7(3) ?
C1 C6 C6 . 5_656 117.3(3) ?
N1 C7 C21 . . 114.6(2) ?
N1 C7 H7A . . 108.6 ?
C21 C7 H7A . . 108.6 ?
N1 C7 H7B . . 108.6 ?
C21 C7 H7B . . 108.6 ?
H7A C7 H7B . . 107.6 ?
N1 C8 C31 . . 115.4(2) ?
N1 C8 H8A . . 108.4 ?
C31 C8 H8A . . 108.4 ?
N1 C8 H8B . . 108.4 ?
C31 C8 H8B . . 108.4 ?
H8A C8 H8B . . 107.5 ?
C12 C11 P1 . . 113.5(2) ?
C12 C11 H11A . . 108.9 ?
P1 C11 H11A . . 108.9 ?
C12 C11 H11B . . 108.9 ?
P1 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C13A C12 C11 . . 128.6(10) ?
C11 C12 C13 . . 112.2(3) ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12B . . 109.2 ?
C13 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C13A C12 H12C . . 105.2 ?
C11 C12 H12C . . 105.2 ?
C13A C12 H12D . . 105.2 ?
C11 C12 H12D . . 105.2 ?
H12C C12 H12D . . 105.9 ?
C14 C13 C12 . . 115.0(3) ?
C14 C13 H13A . . 108.5 ?
C12 C13 H13A . . 108.5 ?
C14 C13 H13B . . 108.5 ?
C12 C13 H13B . . 108.5 ?
H13A C13 H13B . . 107.5 ?
C15 C14 C13 . . 114.0(4) ?
C15 C14 H14A . . 108.8 ?
C13 C14 H14A . . 108.8 ?
C15 C14 H14B . . 108.8 ?
C13 C14 H14B . . 108.8 ?
H14A C14 H14B . . 107.6 ?
C16 C15 C14 . . 112.4(3) ?
C16 C15 H15A . . 109.1 ?
C14 C15 H15A . . 109.1 ?
C16 C15 H15B . . 109.1 ?
C14 C15 H15B . . 109.1 ?
H15A C15 H15B . . 107.9 ?
C17 C16 C15 . . 114.1(3) ?
C17 C16 H16A . . 108.7 ?
C15 C16 H16A . . 108.7 ?
C17 C16 H16B . . 108.7 ?
C15 C16 H16B . . 108.7 ?
H16A C16 H16B . . 107.6 ?
C18 C17 C16 . . 113.6(4) ?
C18 C17 H17A . . 108.8 ?
C16 C17 H17A . . 108.8 ?
C18 C17 H17B . . 108.8 ?
C16 C17 H17B . . 108.8 ?
H17A C17 H17B . . 107.7 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C12 C13A C14A . . 112.0(15) ?
C12 C13A H13C . . 109.2 ?
C14A C13A H13C . . 109.2 ?
C12 C13A H13D . . 109.2 ?
C14A C13A H13D . . 109.2 ?
H13C C13A H13D . . 107.9 ?
C15A C14A C13A . . 111.5(15) ?
C15A C14A H14C . . 109.3 ?
C13A C14A H14C . . 109.3 ?
C15A C14A H14D . . 109.3 ?
C13A C14A H14D . . 109.3 ?
H14C C14A H14D . . 108.0 ?
C16A C15A C14A . . 121.7(17) ?
C16A C15A H15C . . 106.9 ?
C14A C15A H15C . . 106.9 ?
C16A C15A H15D . . 106.9 ?
C14A C15A H15D . . 106.9 ?
H15C C15A H15D . . 106.7 ?
C15A C16A C17A . . 112.8(16) ?
C15A C16A H16C . . 109.0 ?
C17A C16A H16C . . 109.0 ?
C15A C16A H16D . . 109.0 ?
C17A C16A H16D . . 109.0 ?
H16C C16A H16D . . 107.8 ?
C18A C17A C16A . . 109.8(18) ?
C18A C17A H17C . . 109.7 ?
C16A C17A H17C . . 109.7 ?
C18A C17A H17D . . 109.7 ?
C16A C17A H17D . . 109.7 ?
H17C C17A H17D . . 108.2 ?
C17A C18A H18D . . 109.5 ?
C17A C18A H18E . . 109.5 ?
H18D C18A H18E . . 109.5 ?
C17A C18A H18F . . 109.5 ?
H18D C18A H18F . . 109.5 ?
H18E C18A H18F . . 109.5 ?
C22 C21 C26 . . 118.5(3) ?
C22 C21 C7 . . 122.5(3) ?
C26 C21 C7 . . 119.0(3) ?
C21 C22 C23 . . 120.4(3) ?
C21 C22 H22 . . 119.8 ?
C23 C22 H22 . . 119.8 ?
C24 C23 C22 . . 120.2(3) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C25 . . 120.2(3) ?
C23 C24 H24 . . 119.9 ?
C25 C24 H24 . . 119.9 ?
C24 C25 C26 . . 119.9(3) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C25 C26 C21 . . 120.8(3) ?
C25 C26 H26 . . 119.6 ?
C21 C26 H26 . . 119.6 ?
C36 C31 C32 . . 118.2(3) ?
C36 C31 C8 . . 121.5(3) ?
C32 C31 C8 . . 120.2(3) ?
C31 C32 C33 . . 121.5(3) ?
C31 C32 H32 . . 119.3 ?
C33 C32 H32 . . 119.3 ?
C34 C33 C32 . . 120.0(4) ?
C34 C33 H33 . . 120.0 ?
C32 C33 H33 . . 120.0 ?
C33 C34 C35 . . 119.3(3) ?
C33 C34 H34 . . 120.3 ?
C35 C34 H34 . . 120.3 ?
C34 C35 C36 . . 120.5(3) ?
C34 C35 H35 . . 119.8 ?
C36 C35 H35 . . 119.8 ?
C31 C36 C35 . . 120.5(3) ?
C31 C36 H36 . . 119.8 ?
C35 C36 H36 . . 119.8 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 P1 C1 C6 . . . . -125.67(19) ?
C11 P1 C1 C6 . . . . 105.1(2) ?
C5 P1 C1 C6 5_656 . . . -2.4(2) ?
O1 P1 C1 C2 . . . . 57.6(3) ?
C11 P1 C1 C2 . . . . -71.6(3) ?
C5 P1 C1 C2 5_656 . . . -179.2(3) ?
C6 C1 C2 C3 . . . . -1.4(4) ?
P1 C1 C2 C3 . . . . 175.1(2) ?
C7 N1 C3 C4 . . . . -176.0(2) ?
C8 N1 C3 C4 . . . . 0.8(4) ?
C7 N1 C3 C2 . . . . 3.3(4) ?
C8 N1 C3 C2 . . . . -179.8(2) ?
C1 C2 C3 N1 . . . . -177.6(2) ?
C1 C2 C3 C4 . . . . 1.7(4) ?
N1 C3 C4 C5 . . . . 178.9(2) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
C3 C4 C5 C6 . . . . -1.2(4) ?
C3 C4 C5 P1 . . . 5_656 178.6(2) ?
C4 C5 C6 C1 . . . . 1.6(4) ?
P1 C5 C6 C1 5_656 . . . -178.3(2) ?
C4 C5 C6 C6 . . . 5_656 -177.6(3) ?
P1 C5 C6 C6 5_656 . . 5_656 2.5(4) ?
C2 C1 C6 C5 . . . . -0.3(4) ?
P1 C1 C6 C5 . . . . -177.7(2) ?
C2 C1 C6 C6 . . . 5_656 178.9(3) ?
P1 C1 C6 C6 . . . 5_656 1.5(4) ?
C3 N1 C7 C21 . . . . -104.9(3) ?
C8 N1 C7 C21 . . . . 78.1(3) ?
C3 N1 C8 C31 . . . . -73.3(3) ?
C7 N1 C8 C31 . . . . 103.7(3) ?
O1 P1 C11 C12 . . . . -64.8(3) ?
C5 P1 C11 C12 5_656 . . . 164.7(2) ?
C1 P1 C11 C12 . . . . 66.1(3) ?
P1 C11 C12 C13A . . . . 158.5(15) ?
P1 C11 C12 C13 . . . . -164.7(2) ?
C11 C12 C13 C14 . . . . -64.1(4) ?
C12 C13 C14 C15 . . . . 173.3(3) ?
C13 C14 C15 C16 . . . . -179.2(4) ?
C14 C15 C16 C17 . . . . 172.3(4) ?
C15 C16 C17 C18 . . . . 66.5(5) ?
C11 C12 C13A C14A . . . . 37.(3) ?
C12 C13A C14A C15A . . . . -179.8(19) ?
C13A C14A C15A C16A . . . . 178.(2) ?
C14A C15A C16A C17A . . . . -175.(2) ?
C15A C16A C17A C18A . . . . -177.(2) ?
N1 C7 C21 C22 . . . . 12.8(4) ?
N1 C7 C21 C26 . . . . -167.9(3) ?
C26 C21 C22 C23 . . . . 0.7(4) ?
C7 C21 C22 C23 . . . . -179.9(3) ?
C21 C22 C23 C24 . . . . 0.1(5) ?
C22 C23 C24 C25 . . . . -0.9(5) ?
C23 C24 C25 C26 . . . . 0.9(5) ?
C24 C25 C26 C21 . . . . -0.1(5) ?
C22 C21 C26 C25 . . . . -0.8(4) ?
C7 C21 C26 C25 . . . . 179.8(3) ?
N1 C8 C31 C36 . . . . -16.8(4) ?
N1 C8 C31 C32 . . . . 164.8(3) ?
C36 C31 C32 C33 . . . . -0.2(5) ?
C8 C31 C32 C33 . . . . 178.2(3) ?
C31 C32 C33 C34 . . . . -0.1(6) ?
C32 C33 C34 C35 . . . . -0.1(6) ?
C33 C34 C35 C36 . . . . 0.6(6) ?
C32 C31 C36 C35 . . . . 0.7(5) ?
C8 C31 C36 C35 . . . . -177.6(3) ?
C34 C35 C36 C31 . . . . -0.9(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 O1 5_666 0.95 2.40 3.345(4) 171.4 ?
C7 H7B O1 5_666 0.99 2.51 3.412(4) 151.5 ?

