# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_100654lt_0m
#TrackingRef '100654lt_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H30 N O4 P'
_chemical_formula_weight         607.61

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6945(2)
_cell_length_b                   11.2700(3)
_cell_length_c                   15.8376(4)
_cell_angle_alpha                92.4460(10)
_cell_angle_beta                 101.1100(10)
_cell_angle_gamma                113.8460(10)
_cell_volume                     1538.91(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9645
_cell_measurement_theta_min      2.5365
_cell_measurement_theta_max      26.3770

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7190
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            25576
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.32
_diffrn_reflns_theta_max         26.40
_reflns_number_total             6265
_reflns_number_gt                5474
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_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)+(0.0743P)²+0.5587P] 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         6265
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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
C1 C 0.57655(18) 1.16321(15) 0.34227(11) 0.0188(3) Uani 1 1 d . . .
C2 C 0.41323(17) 1.08734(15) 0.31982(10) 0.0171(3) Uani 1 1 d . . .
C3 C 0.37665(18) 1.00738(15) 0.23797(10) 0.0176(3) Uani 1 1 d . . .
C4 C 0.51349(18) 1.03520(15) 0.21318(10) 0.0185(3) Uani 1 1 d . . .
C5 C 0.38278(17) 1.17177(15) 0.48976(10) 0.0172(3) Uani 1 1 d . . .
C6 C 0.47587(18) 1.30693(16) 0.50578(11) 0.0208(3) Uani 1 1 d . . .
H6 H 0.4873 1.3569 0.4587 0.025 Uiso 1 1 calc R . .
C7 C 0.55120(18) 1.36794(16) 0.58980(11) 0.0209(3) Uani 1 1 d . . .
H7 H 0.6153 1.4593 0.5997 0.025 Uiso 1 1 calc R . .
C8 C 0.53407(18) 1.29678(16) 0.66017(11) 0.0218(3) Uani 1 1 d . . .
C9 C 0.43955(18) 1.16311(16) 0.64325(11) 0.0212(3) Uani 1 1 d . . .
H9 H 0.4257 1.1136 0.6905 0.025 Uiso 1 1 calc R . .
C10 C 0.36492(18) 1.10002(16) 0.55935(11) 0.0187(3) Uani 1 1 d . . .
H10 H 0.3020 1.0084 0.5495 0.022 Uiso 1 1 calc R . .
C11 C 0.6151(2) 1.36152(19) 0.75168(12) 0.0328(4) Uani 1 1 d . . .
H11A H 0.7176 1.3606 0.7659 0.049 Uiso 1 1 calc R . .
H11B H 0.5538 1.3140 0.7918 0.049 Uiso 1 1 calc R . .
H11C H 0.6268 1.4522 0.7571 0.049 Uiso 1 1 calc R . .
C12 C 0.18218(17) 1.18803(15) 0.33523(10) 0.0173(3) Uani 1 1 d . . .
C13 C 0.09491(18) 1.22557(16) 0.38207(11) 0.0201(3) Uani 1 1 d . . .
H13 H 0.0917 1.2043 0.4393 0.024 Uiso 1 1 calc R . .
C14 C 0.01295(18) 1.29391(16) 0.34509(11) 0.0213(3) Uani 1 1 d . . .
H14 H -0.0471 1.3183 0.3770 0.026 Uiso 1 1 calc R . .
C15 C 0.01758(18) 1.32724(16) 0.26164(11) 0.0210(3) Uani 1 1 d . . .
C16 C 0.10490(19) 1.28922(16) 0.21584(11) 0.0221(3) Uani 1 1 d . . .
H16 H 0.1083 1.3106 0.1587 0.027 Uiso 1 1 calc R . .
C17 C 0.18729(18) 1.22056(16) 0.25199(11) 0.0205(3) Uani 1 1 d . . .
H17 H 0.2470 1.1959 0.2199 0.025 Uiso 1 1 calc R . .
C18 C -0.0735(2) 1.40046(18) 0.22125(12) 0.0285(4) Uani 1 1 d . . .
H18A H -0.1819 1.3544 0.2247 0.043 Uiso 1 1 calc R . .
H18B H -0.0679 1.4052 0.1603 0.043 Uiso 1 1 calc R . .
H18C H -0.0296 1.4892 0.2526 0.043 Uiso 1 1 calc R . .
C19 C 0.14631(17) 0.93203(15) 0.38485(10) 0.0163(3) Uani 1 1 d . . .
C20 C -0.01132(18) 0.90014(16) 0.37399(11) 0.0199(3) Uani 1 1 d . . .
H20 H -0.0498 0.9641 0.3607 0.024 Uiso 1 1 calc R . .
C21 C -0.11172(18) 0.77448(16) 0.38264(11) 0.0218(3) Uani 1 1 d . . .
H21 H -0.2191 0.7531 0.3747 0.026 Uiso 1 1 calc R . .
C22 C -0.05866(19) 0.67919(15) 0.40263(11) 0.0204(3) Uani 1 1 d . . .
C23 C 0.09838(19) 0.71163(16) 0.41295(11) 0.0227(4) Uani 1 1 d . . .
H23 H 0.1367 0.6476 0.4264 0.027 Uiso 1 1 calc R . .
C24 C 0.20011(18) 0.83667(16) 0.40376(11) 0.0210(3) Uani 1 1 d . . .
H24 H 0.3071 0.8573 0.4104 0.025 Uiso 1 1 calc R . .
C25 C -0.1705(2) 0.54523(17) 0.41387(13) 0.0293(4) Uani 1 1 d . . .
H25A H -0.2227 0.5529 0.4596 0.044 Uiso 1 1 calc R . .
H25B H -0.1139 0.4915 0.4301 0.044 Uiso 1 1 calc R . .
H25C H -0.2477 0.5040 0.3592 0.044 Uiso 1 1 calc R . .
C26 C 0.22885(18) 0.91091(16) 0.19368(10) 0.0201(3) Uani 1 1 d . . .
C27 C 0.10603(19) 0.82529(17) 0.15777(11) 0.0225(4) Uani 1 1 d . . .
C28 C -0.03601(18) 0.71840(16) 0.11380(11) 0.0224(4) Uani 1 1 d . . .
C29 C -0.1668(2) 0.67976(18) 0.14876(12) 0.0294(4) Uani 1 1 d . . .
H29 H -0.1628 0.7257 0.2015 0.035 Uiso 1 1 calc R . .
C30 C -0.3019(2) 0.5748(2) 0.10661(14) 0.0354(4) Uani 1 1 d . . .
H30 H -0.3904 0.5482 0.1308 0.042 Uiso 1 1 calc R . .
C31 C -0.3093(2) 0.50810(18) 0.02945(13) 0.0337(5) Uani 1 1 d . . .
H31 H -0.4032 0.4368 0.0003 0.040 Uiso 1 1 calc R . .
C32 C -0.1810(2) 0.54474(18) -0.00521(12) 0.0331(4) Uani 1 1 d . . .
H32 H -0.1860 0.4981 -0.0579 0.040 Uiso 1 1 calc R . .
C33 C -0.0440(2) 0.64970(18) 0.03658(12) 0.0297(4) Uani 1 1 d . . .
H33 H 0.0445 0.6747 0.0124 0.036 Uiso 1 1 calc R . .
C34 C 0.55721(19) 0.98017(16) 0.14458(11) 0.0201(3) Uani 1 1 d . . .
C35 C 0.4466(2) 0.88863(16) 0.07499(11) 0.0226(3) Uani 1 1 d . . .
H35 H 0.3393 0.8628 0.0719 0.027 Uiso 1 1 calc R . .
C36 C 0.4924(2) 0.83623(17) 0.01125(11) 0.0245(4) Uani 1 1 d . . .
H36 H 0.4174 0.7747 -0.0357 0.029 Uiso 1 1 calc R . .
C37 C 0.6493(2) 0.87423(17) 0.01633(11) 0.0249(4) Uani 1 1 d . . .
C38 C 0.7619(2) 0.96498(18) 0.08298(12) 0.0268(4) Uani 1 1 d . . .
H38 H 0.8687 0.9912 0.0847 0.032 Uiso 1 1 calc R . .
C39 C 0.7156(2) 1.01645(17) 0.14673(11) 0.0243(4) Uani 1 1 d . . .
H39 H 0.7919 1.0778 0.1933 0.029 Uiso 1 1 calc R . .
N1 N 0.69713(19) 0.81751(15) -0.05031(10) 0.0288(3) Uani 1 1 d . . .
O1 O 0.63471(12) 1.12851(11) 0.27496(7) 0.0198(2) Uani 1 1 d . . .
O2 O 0.66806(13) 1.24381(11) 0.40315(8) 0.0256(3) Uani 1 1 d . . .
O3 O 0.59565(18) 0.72875(14) -0.10570(9) 0.0393(3) Uani 1 1 d . . .
O4 O 0.83576(16) 0.85924(15) -0.04928(9) 0.0384(3) Uani 1 1 d . . .
P1 P 0.28485(4) 1.09471(4) 0.38007(3) 0.01507(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.219(2) . ?
C1 O1 1.4076(19) . ?
C1 C2 1.424(2) . ?
C2 C3 1.443(2) . ?
C2 P1 1.7323(16) . ?
C3 C4 1.374(2) . ?
C3 C26 1.420(2) . ?
C4 O1 1.3835(19) . ?
C4 C34 1.441(2) . ?
C5 C10 1.391(2) . ?
C5 C6 1.402(2) . ?
C5 P1 1.8006(16) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(2) . ?
C8 C11 1.503(2) . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.388(2) . ?
C12 C13 1.396(2) . ?
C12 P1 1.7997(15) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(2) . ?
C15 C18 1.512(2) . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.392(2) . ?
C19 C20 1.394(2) . ?
C19 P1 1.7975(15) . ?
C20 C21 1.387(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(2) . ?
C22 C25 1.503(2) . ?
C23 C24 1.389(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.198(2) . ?
C27 C28 1.432(2) . ?
C28 C33 1.391(3) . ?
C28 C29 1.396(3) . ?
C29 C30 1.379(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.381(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.373(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.387(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.408(2) . ?
C34 C39 1.413(2) . ?
C35 C36 1.378(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.388(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.383(3) . ?
C37 N1 1.452(2) . ?
C38 C39 1.375(2) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
N1 O4 1.228(2) . ?
N1 O3 1.239(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 118.35(14) . . ?
O2 C1 C2 135.24(15) . . ?
O1 C1 C2 106.41(13) . . ?
C1 C2 C3 107.35(13) . . ?
C1 C2 P1 125.30(12) . . ?
C3 C2 P1 127.34(12) . . ?
C4 C3 C26 125.76(15) . . ?
C4 C3 C2 107.34(14) . . ?
C26 C3 C2 126.76(14) . . ?
C3 C4 O1 109.51(14) . . ?
C3 C4 C34 134.47(15) . . ?
O1 C4 C34 115.62(14) . . ?
C10 C5 C6 119.24(15) . . ?
C10 C5 P1 121.12(12) . . ?
C6 C5 P1 119.62(12) . . ?
C7 C6 C5 120.39(15) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.83(15) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 118.05(15) . . ?
C9 C8 C11 120.49(16) . . ?
C7 C8 C11 121.46(16) . . ?
C10 C9 C8 121.89(15) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C5 119.59(15) . . ?
C9 C10 H10 120.2 . . ?
C5 C10 H10 120.2 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 119.62(14) . . ?
C17 C12 P1 119.31(12) . . ?
C13 C12 P1 121.05(12) . . ?
C14 C13 C12 119.98(15) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.83(15) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 118.52(14) . . ?
C16 C15 C18 120.86(15) . . ?
C14 C15 C18 120.61(15) . . ?
C17 C16 C15 121.26(15) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 119.78(15) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 119.26(14) . . ?
C24 C19 P1 118.46(11) . . ?
C20 C19 P1 122.22(12) . . ?
C21 C20 C19 119.63(14) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 121.47(14) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 118.51(15) . . ?
C23 C22 C25 121.62(15) . . ?
C21 C22 C25 119.87(15) . . ?
C22 C23 C24 120.69(15) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 120.44(14) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C3 177.06(17) . . ?
C26 C27 C28 176.61(18) . . ?
C33 C28 C29 119.20(16) . . ?
C33 C28 C27 120.19(16) . . ?
C29 C28 C27 120.60(16) . . ?
C30 C29 C28 119.95(18) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 120.45(19) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C32 C31 C30 120.07(17) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C33 120.19(18) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C28 120.13(18) . . ?
C32 C33 H33 119.9 . . ?
C28 C33 H33 119.9 . . ?
C35 C34 C39 118.03(15) . . ?
C35 C34 C4 122.12(15) . . ?
C39 C34 C4 119.84(15) . . ?
C36 C35 C34 120.60(16) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 119.35(16) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C38 C37 C36 121.94(16) . . ?
C38 C37 N1 118.87(16) . . ?
C36 C37 N1 119.19(16) . . ?
C39 C38 C37 118.52(16) . . ?
C39 C38 H38 120.7 . . ?
C37 C38 H38 120.7 . . ?
C38 C39 C34 121.55(17) . . ?
C38 C39 H39 119.2 . . ?
C34 C39 H39 119.2 . . ?
O4 N1 O3 122.97(16) . . ?
O4 N1 C37 118.76(16) . . ?
O3 N1 C37 118.27(16) . . ?
C4 O1 C1 109.39(12) . . ?
C2 P1 C19 109.78(7) . . ?
C2 P1 C12 112.31(7) . . ?
C19 P1 C12 108.75(7) . . ?
C2 P1 C5 111.71(7) . . ?
C19 P1 C5 107.85(7) . . ?
C12 P1 C5 106.27(7) . . ?

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
O2 C1 C2 C3 -179.02(18) . . . . ?
O1 C1 C2 C3 0.01(16) . . . . ?
O2 C1 C2 P1 2.2(3) . . . . ?
O1 C1 C2 P1 -178.74(11) . . . . ?
C1 C2 C3 C4 0.00(17) . . . . ?
P1 C2 C3 C4 178.71(12) . . . . ?
C1 C2 C3 C26 175.95(15) . . . . ?
P1 C2 C3 C26 -5.3(2) . . . . ?
C26 C3 C4 O1 -176.01(14) . . . . ?
C2 C3 C4 O1 -0.01(17) . . . . ?
C26 C3 C4 C34 -3.8(3) . . . . ?
C2 C3 C4 C34 172.20(17) . . . . ?
C10 C5 C6 C7 1.0(2) . . . . ?
P1 C5 C6 C7 179.57(12) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C6 C7 C8 C11 179.95(16) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C11 C8 C9 C10 -179.02(15) . . . . ?
C8 C9 C10 C5 -0.8(2) . . . . ?
C6 C5 C10 C9 -0.1(2) . . . . ?
P1 C5 C10 C9 -178.64(12) . . . . ?
C17 C12 C13 C14 0.6(2) . . . . ?
P1 C12 C13 C14 -177.99(12) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C13 C14 C15 C18 179.32(15) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
C18 C15 C16 C17 -179.19(15) . . . . ?
C15 C16 C17 C12 0.5(2) . . . . ?
C13 C12 C17 C16 -0.4(2) . . . . ?
P1 C12 C17 C16 178.14(12) . . . . ?
C24 C19 C20 C21 0.4(2) . . . . ?
P1 C19 C20 C21 -176.80(12) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
C20 C21 C22 C25 178.33(16) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C25 C22 C23 C24 -178.87(16) . . . . ?
C22 C23 C24 C19 0.6(3) . . . . ?
C20 C19 C24 C23 -0.9(2) . . . . ?
P1 C19 C24 C23 176.36(13) . . . . ?
C4 C3 C26 C27 76(4) . . . . ?
C2 C3 C26 C27 -100(3) . . . . ?
C3 C26 C27 C28 -39(6) . . . . ?
C26 C27 C28 C33 -42(3) . . . . ?
C26 C27 C28 C29 136(3) . . . . ?
C33 C28 C29 C30 -0.2(3) . . . . ?
C27 C28 C29 C30 -178.61(17) . . . . ?
C28 C29 C30 C31 -0.6(3) . . . . ?
C29 C30 C31 C32 1.0(3) . . . . ?
C30 C31 C32 C33 -0.7(3) . . . . ?
C31 C32 C33 C28 0.0(3) . . . . ?
C29 C28 C33 C32 0.5(3) . . . . ?
C27 C28 C33 C32 178.92(16) . . . . ?
C3 C4 C34 C35 11.1(3) . . . . ?
O1 C4 C34 C35 -177.05(14) . . . . ?
C3 C4 C34 C39 -167.89(17) . . . . ?
O1 C4 C34 C39 4.0(2) . . . . ?
C39 C34 C35 C36 0.1(2) . . . . ?
C4 C34 C35 C36 -178.86(15) . . . . ?
C34 C35 C36 C37 0.2(2) . . . . ?
C35 C36 C37 C38 -1.0(3) . . . . ?
C35 C36 C37 N1 179.19(15) . . . . ?
C36 C37 C38 C39 1.4(3) . . . . ?
N1 C37 C38 C39 -178.81(15) . . . . ?
C37 C38 C39 C34 -1.0(3) . . . . ?
C35 C34 C39 C38 0.2(2) . . . . ?
C4 C34 C39 C38 179.28(16) . . . . ?
C38 C37 N1 O4 -5.6(2) . . . . ?
C36 C37 N1 O4 174.19(15) . . . . ?
C38 C37 N1 O3 174.27(16) . . . . ?
C36 C37 N1 O3 -5.9(2) . . . . ?
C3 C4 O1 C1 0.01(17) . . . . ?
C34 C4 O1 C1 -173.83(13) . . . . ?
O2 C1 O1 C4 179.21(14) . . . . ?
C2 C1 O1 C4 -0.01(16) . . . . ?
C1 C2 P1 C19 -136.90(13) . . . . ?
C3 C2 P1 C19 44.61(16) . . . . ?
C1 C2 P1 C12 101.98(14) . . . . ?
C3 C2 P1 C12 -76.51(15) . . . . ?
C1 C2 P1 C5 -17.32(16) . . . . ?
C3 C2 P1 C5 164.19(13) . . . . ?
C24 C19 P1 C2 46.19(15) . . . . ?
C20 C19 P1 C2 -136.64(14) . . . . ?
C24 C19 P1 C12 169.42(12) . . . . ?
C20 C19 P1 C12 -13.40(16) . . . . ?
C24 C19 P1 C5 -75.74(14) . . . . ?
C20 C19 P1 C5 101.44(14) . . . . ?
C17 C12 P1 C2 13.13(16) . . . . ?
C13 C12 P1 C2 -168.30(13) . . . . ?
C17 C12 P1 C19 -108.57(13) . . . . ?
C13 C12 P1 C19 69.99(14) . . . . ?
C17 C12 P1 C5 135.57(13) . . . . ?
C13 C12 P1 C5 -45.87(15) . . . . ?
C10 C5 P1 C2 -110.25(13) . . . . ?
C6 C5 P1 C2 71.25(14) . . . . ?
C10 C5 P1 C19 10.46(15) . . . . ?
C6 C5 P1 C19 -168.04(12) . . . . ?
C10 C5 P1 C12 126.94(13) . . . . ?
C6 C5 P1 C12 -51.56(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.166


_database_code_depnum_ccdc_archive 'CCDC 901699'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_101227lt_0m
#TrackingRef '101227LT_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H23 Cl2 F3 N O4 P'
_chemical_formula_weight         728.45

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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_hall  '-P 2yn'

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

_cell_length_a                   15.3256(5)
_cell_length_b                   9.7698(3)
_cell_length_c                   22.1934(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.145(2)
_cell_angle_gamma                90.00
_cell_volume                     3322.96(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7171
_cell_measurement_theta_min      2.2775
_cell_measurement_theta_max      26.2799

_exptl_crystal_description       Blade
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6256
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            24139
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.12
_reflns_number_total             5908
_reflns_number_gt                4404
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_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)+(0.0937P)²+6.1089P] 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         5908
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.2080
_refine_ls_wR_factor_gt          0.1883
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.93736(16) 0.39878(17) 0.78323(12) 0.1243(10) Uani 1 1 d . . .
Cl1 Cl 0.95575(10) 0.68931(13) 0.78057(6) 0.0612(4) Uani 1 1 d . . .
P1 P 0.76914(6) 0.36557(10) 0.04340(4) 0.0297(3) Uani 1 1 d . . .
F1 F 1.10642(15) 0.1185(3) -0.02213(12) 0.0478(7) Uani 1 1 d . . .
F2 F 0.57023(18) -0.1022(3) 0.13685(13) 0.0559(7) Uani 1 1 d . . .
F3 F 0.83357(17) 0.7653(2) 0.23710(11) 0.0450(6) Uani 1 1 d . . .
O1 O 0.69861(17) 0.5498(3) -0.10614(11) 0.0320(6) Uani 1 1 d . . .
O2 O 0.82926(17) 0.5785(3) -0.06022(13) 0.0383(7) Uani 1 1 d . . .
O3 O 0.42111(19) 0.5108(3) -0.34192(13) 0.0414(7) Uani 1 1 d . . .
O4 O 0.32975(19) 0.3839(3) -0.29301(13) 0.0411(7) Uani 1 1 d . . .
N1 N 0.3955(2) 0.4563(3) -0.29521(15) 0.0343(8) Uani 1 1 d . . .
C39 C 0.8936(5) 0.5471(6) 0.8038(3) 0.087(2) Uani 1 1 d . . .
H39A H 0.8878 0.5490 0.8482 0.104 Uiso 1 1 calc R . .
H39B H 0.8343 0.5543 0.7863 0.104 Uiso 1 1 calc R . .
C1 C 1.0290(3) 0.1792(4) -0.0077(2) 0.0403(10) Uani 1 1 d . . .
C2 C 0.9694(3) 0.1988(6) -0.0521(2) 0.0542(13) Uani 1 1 d . . .
H2 H 0.9813 0.1713 -0.0923 0.065 Uiso 1 1 calc R . .
C3 C 0.8902(3) 0.2604(5) -0.0372(2) 0.0483(11) Uani 1 1 d . . .
H3 H 0.8471 0.2750 -0.0674 0.058 Uiso 1 1 calc R . .
C4 C 0.8745(2) 0.3002(4) 0.02153(18) 0.0328(9) Uani 1 1 d . . .
C5 C 0.7144(2) 0.4364(4) -0.01742(17) 0.0311(8) Uani 1 1 d . . .
C6 C 0.6275(2) 0.4140(4) -0.04031(17) 0.0288(8) Uani 1 1 d . . .
C7 C 0.5597(2) 0.3376(4) -0.01279(17) 0.0307(8) Uani 1 1 d . . .
C8 C 0.5025(2) 0.2748(4) 0.01197(17) 0.0330(9) Uani 1 1 d . . .
C9 C 0.4402(3) 0.2009(4) 0.04154(18) 0.0355(9) Uani 1 1 d . . .
C10 C 0.3874(3) 0.1348(4) 0.06949(18) 0.0376(9) Uani 1 1 d . . .
C11 C 0.3290(3) 0.0512(4) 0.10369(18) 0.0371(9) Uani 1 1 d . . .
C12 C 0.2501(3) 0.1029(5) 0.1234(2) 0.0548(13) Uani 1 1 d . . .
H12 H 0.2335 0.1938 0.1134 0.066 Uiso 1 1 calc R . .
C13 C 0.1952(3) 0.0216(5) 0.1577(3) 0.0652(16) Uani 1 1 d . . .
H13 H 0.1411 0.0573 0.1714 0.078 Uiso 1 1 calc R . .
C14 C 0.2187(3) -0.1110(5) 0.1722(2) 0.0489(12) Uani 1 1 d . . .
H14 H 0.1813 -0.1657 0.1964 0.059 Uiso 1 1 calc R . .
C15 C 0.6156(3) 0.0070(4) 0.1153(2) 0.0402(10) Uani 1 1 d . . .
C16 C 0.5982(3) 0.1332(4) 0.13916(19) 0.0385(10) Uani 1 1 d . . .
H16 H 0.5551 0.1451 0.1694 0.046 Uiso 1 1 calc R . .
C17 C 0.6460(3) 0.2432(4) 0.11749(18) 0.0335(9) Uani 1 1 d . . .
H17 H 0.6356 0.3323 0.1330 0.040 Uiso 1 1 calc R . .
C18 C 0.7087(2) 0.2247(4) 0.07355(17) 0.0303(8) Uani 1 1 d . . .
C19 C 0.7238(3) 0.0934(4) 0.05016(19) 0.0360(9) Uani 1 1 d . . .
H19 H 0.7666 0.0802 0.0199 0.043 Uiso 1 1 calc R . .
C20 C 0.6763(3) -0.0166(4) 0.0713(2) 0.0424(10) Uani 1 1 d . . .
H20 H 0.6855 -0.1061 0.0558 0.051 Uiso 1 1 calc R . .
C21 C 0.6209(2) 0.4823(4) -0.09410(17) 0.0297(8) Uani 1 1 d . . .
C22 C 0.7572(3) 0.5246(4) -0.05874(18) 0.0324(9) Uani 1 1 d . . .
C23 C 0.5561(2) 0.4885(4) -0.14126(17) 0.0297(8) Uani 1 1 d . . .
C24 C 0.5720(3) 0.5681(4) -0.19294(18) 0.0344(9) Uani 1 1 d . . .
H24 H 0.6209 0.6278 -0.1937 0.041 Uiso 1 1 calc R . .
C25 C 0.5183(3) 0.5609(4) -0.24206(18) 0.0340(9) Uani 1 1 d . . .
H25 H 0.5301 0.6144 -0.2768 0.041 Uiso 1 1 calc R . .
C26 C 0.4466(3) 0.4752(4) -0.24069(18) 0.0317(8) Uani 1 1 d . . .
C27 C 0.4250(3) 0.4023(4) -0.18904(18) 0.0334(9) Uani 1 1 d . . .
H27 H 0.3735 0.3482 -0.1878 0.040 Uiso 1 1 calc R . .
C28 C 0.4795(3) 0.4098(4) -0.13977(18) 0.0334(9) Uani 1 1 d . . .
H28 H 0.4650 0.3609 -0.1042 0.040 Uiso 1 1 calc R . .
C29 C 0.3516(3) -0.0830(4) 0.1178(2) 0.0405(10) Uani 1 1 d . . .
H29 H 0.4056 -0.1194 0.1042 0.049 Uiso 1 1 calc R . .
C30 C 0.2960(3) -0.1633(4) 0.1516(2) 0.0415(10) Uani 1 1 d . . .
H30 H 0.3114 -0.2553 0.1605 0.050 Uiso 1 1 calc R . .
C31 C 1.0158(3) 0.2168(5) 0.0506(2) 0.0426(10) Uani 1 1 d . . .
H31 H 1.0592 0.2015 0.0804 0.051 Uiso 1 1 calc R . .
C32 C 0.9371(3) 0.2779(5) 0.06498(19) 0.0406(10) Uani 1 1 d . . .
H32 H 0.9261 0.3047 0.1054 0.049 Uiso 1 1 calc R . .
C33 C 0.7865(2) 0.4857(4) 0.10356(17) 0.0309(8) Uani 1 1 d . . .
C34 C 0.7997(3) 0.4420(4) 0.16282(17) 0.0332(9) Uani 1 1 d . . .
H34 H 0.7974 0.3472 0.1721 0.040 Uiso 1 1 calc R . .
C35 C 0.8161(3) 0.5361(4) 0.20813(18) 0.0367(9) Uani 1 1 d . . .
H35 H 0.8251 0.5076 0.2486 0.044 Uiso 1 1 calc R . .
C36 C 0.8189(3) 0.6723(4) 0.19248(19) 0.0374(9) Uani 1 1 d . . .
C37 C 0.8079(3) 0.7194(4) 0.13522(18) 0.0360(9) Uani 1 1 d . . .
H37 H 0.8117 0.8144 0.1266 0.043 Uiso 1 1 calc R . .
C38 C 0.7913(3) 0.6256(4) 0.08990(18) 0.0341(9) Uani 1 1 d . . .
H38 H 0.7831 0.6560 0.0496 0.041 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
Cl2 C39 1.661(6) . ?
Cl1 C39 1.762(6) . ?
P1 C5 1.732(4) . ?
P1 C18 1.790(4) . ?
P1 C33 1.797(4) . ?
P1 C4 1.804(4) . ?
F1 C1 1.364(5) . ?
F2 C15 1.361(5) . ?
F3 C36 1.362(5) . ?
O1 C21 1.388(4) . ?
O1 C22 1.403(5) . ?
O2 C22 1.223(5) . ?
O3 N1 1.231(4) . ?
O4 N1 1.232(4) . ?
N1 C26 1.452(5) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C1 C2 1.356(6) . ?
C1 C31 1.361(6) . ?
C2 C3 1.396(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9500 . ?
C4 C32 1.376(6) . ?
C5 C22 1.420(5) . ?
C5 C6 1.442(5) . ?
C6 C21 1.371(5) . ?
C6 C7 1.418(5) . ?
C7 C8 1.204(5) . ?
C8 C9 1.367(6) . ?
C9 C10 1.208(6) . ?
C10 C11 1.431(6) . ?
C11 C12 1.383(6) . ?
C11 C29 1.391(6) . ?
C12 C13 1.386(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(7) . ?
C13 H13 0.9500 . ?
C14 C30 1.371(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(6) . ?
C15 C20 1.370(7) . ?
C16 C17 1.388(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.404(5) . ?
C19 C20 1.381(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C23 1.442(5) . ?
C23 C28 1.404(5) . ?
C23 C24 1.407(5) . ?
C24 C25 1.366(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(6) . ?
C27 C28 1.376(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.381(6) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.384(6) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.397(5) . ?
C33 C38 1.402(5) . ?
C34 C35 1.385(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.376(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.361(6) . ?
C37 C38 1.384(6) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 P1 C18 110.39(18) . . ?
C5 P1 C33 112.88(19) . . ?
C18 P1 C33 107.48(18) . . ?
C5 P1 C4 111.33(19) . . ?
C18 P1 C4 107.06(18) . . ?
C33 P1 C4 107.45(18) . . ?
C21 O1 C22 108.7(3) . . ?
O3 N1 O4 123.0(3) . . ?
O3 N1 C26 118.3(3) . . ?
O4 N1 C26 118.7(3) . . ?
Cl2 C39 Cl1 112.9(3) . . ?
Cl2 C39 H39A 109.0 . . ?
Cl1 C39 H39A 109.0 . . ?
Cl2 C39 H39B 109.0 . . ?
Cl1 C39 H39B 109.0 . . ?
H39A C39 H39B 107.8 . . ?
C2 C1 C31 123.4(4) . . ?
C2 C1 F1 118.4(4) . . ?
C31 C1 F1 118.2(4) . . ?
C1 C2 C3 118.3(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C32 C4 C3 119.6(4) . . ?
C32 C4 P1 119.4(3) . . ?
C3 C4 P1 120.7(3) . . ?
C22 C5 C6 107.0(3) . . ?
C22 C5 P1 121.5(3) . . ?
C6 C5 P1 131.2(3) . . ?
C21 C6 C7 125.4(3) . . ?
C21 C6 C5 107.4(3) . . ?
C7 C6 C5 127.3(3) . . ?
C8 C7 C6 178.3(4) . . ?
C7 C8 C9 177.6(4) . . ?
C10 C9 C8 177.4(4) . . ?
C9 C10 C11 176.5(5) . . ?
C12 C11 C29 119.4(4) . . ?
C12 C11 C10 120.5(4) . . ?
C29 C11 C10 120.1(4) . . ?
C11 C12 C13 119.8(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C30 C14 C13 119.7(4) . . ?
C30 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
F2 C15 C16 118.0(4) . . ?
F2 C15 C20 117.9(4) . . ?
C16 C15 C20 124.1(4) . . ?
C15 C16 C17 117.4(4) . . ?
C15 C16 H16 121.3 . . ?
C17 C16 H16 121.3 . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.8(4) . . ?
C17 C18 P1 121.6(3) . . ?
C19 C18 P1 118.6(3) . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C15 C20 C19 118.1(4) . . ?
C15 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
C6 C21 O1 109.8(3) . . ?
C6 C21 C23 134.5(3) . . ?
O1 C21 C23 115.4(3) . . ?
O2 C22 O1 118.7(3) . . ?
O2 C22 C5 134.2(4) . . ?
O1 C22 C5 107.1(3) . . ?
C28 C23 C24 117.9(4) . . ?
C28 C23 C21 122.3(3) . . ?
C24 C23 C21 119.7(3) . . ?
C25 C24 C23 121.1(4) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 119.4(4) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 121.3(4) . . ?
C25 C26 N1 119.1(3) . . ?
C27 C26 N1 119.5(3) . . ?
C28 C27 C26 118.8(4) . . ?
C28 C27 H27 120.6 . . ?
C26 C27 H27 120.6 . . ?
C27 C28 C23 121.1(4) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C30 C29 C11 120.3(4) . . ?
C30 C29 H29 119.9 . . ?
C11 C29 H29 119.9 . . ?
C14 C30 C29 120.4(4) . . ?
C14 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C1 C31 C32 117.9(4) . . ?
C1 C31 H31 121.0 . . ?
C32 C31 H31 121.0 . . ?
C4 C32 C31 120.9(4) . . ?
C4 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C38 119.6(4) . . ?
C34 C33 P1 121.4(3) . . ?
C38 C33 P1 118.9(3) . . ?
C35 C34 C33 120.4(4) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C34 117.7(4) . . ?
C36 C35 H35 121.2 . . ?
C34 C35 H35 121.2 . . ?
C37 C36 F3 118.2(4) . . ?
C37 C36 C35 124.0(4) . . ?
F3 C36 C35 117.8(4) . . ?
C36 C37 C38 118.5(4) . . ?
C36 C37 H37 120.8 . . ?
C38 C37 H37 120.8 . . ?
C37 C38 C33 119.9(4) . . ?
C37 C38 H38 120.1 . . ?
C33 C38 H38 120.1 . . ?

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
C31 C1 C2 C3 -0.2(8) . . . . ?
F1 C1 C2 C3 179.8(4) . . . . ?
C1 C2 C3 C4 0.3(8) . . . . ?
C2 C3 C4 C32 -0.4(7) . . . . ?
C2 C3 C4 P1 -174.3(4) . . . . ?
C5 P1 C4 C32 160.8(3) . . . . ?
C18 P1 C4 C32 -78.4(4) . . . . ?
C33 P1 C4 C32 36.8(4) . . . . ?
C5 P1 C4 C3 -25.3(4) . . . . ?
C18 P1 C4 C3 95.4(4) . . . . ?
C33 P1 C4 C3 -149.4(4) . . . . ?
C18 P1 C5 C22 -163.5(3) . . . . ?
C33 P1 C5 C22 76.2(4) . . . . ?
C4 P1 C5 C22 -44.7(4) . . . . ?
C18 P1 C5 C6 10.0(4) . . . . ?
C33 P1 C5 C6 -110.3(4) . . . . ?
C4 P1 C5 C6 128.8(4) . . . . ?
C22 C5 C6 C21 2.2(4) . . . . ?
P1 C5 C6 C21 -172.1(3) . . . . ?
C22 C5 C6 C7 -176.9(4) . . . . ?
P1 C5 C6 C7 8.8(6) . . . . ?
C21 C6 C7 C8 -128(14) . . . . ?
C5 C6 C7 C8 51(14) . . . . ?
C6 C7 C8 C9 -69(20) . . . . ?
C7 C8 C9 C10 19(19) . . . . ?
C8 C9 C10 C11 -38(16) . . . . ?
C9 C10 C11 C12 158(7) . . . . ?
C9 C10 C11 C29 -22(8) . . . . ?
C29 C11 C12 C13 1.1(8) . . . . ?
C10 C11 C12 C13 -178.4(5) . . . . ?
C11 C12 C13 C14 -0.3(9) . . . . ?
C12 C13 C14 C30 -1.2(9) . . . . ?
F2 C15 C16 C17 178.9(4) . . . . ?
C20 C15 C16 C17 -0.6(7) . . . . ?
C15 C16 C17 C18 -0.1(6) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C16 C17 C18 P1 178.3(3) . . . . ?
C5 P1 C18 C17 -88.5(4) . . . . ?
C33 P1 C18 C17 35.0(4) . . . . ?
C4 P1 C18 C17 150.2(3) . . . . ?
C5 P1 C18 C19 89.3(3) . . . . ?
C33 P1 C18 C19 -147.2(3) . . . . ?
C4 P1 C18 C19 -32.0(4) . . . . ?
C17 C18 C19 C20 -0.2(6) . . . . ?
P1 C18 C19 C20 -178.1(3) . . . . ?
F2 C15 C20 C19 -178.7(4) . . . . ?
C16 C15 C20 C19 0.8(7) . . . . ?
C18 C19 C20 C15 -0.4(6) . . . . ?
C7 C6 C21 O1 177.8(3) . . . . ?
C5 C6 C21 O1 -1.3(4) . . . . ?
C7 C6 C21 C23 -8.7(7) . . . . ?
C5 C6 C21 C23 172.2(4) . . . . ?
C22 O1 C21 C6 0.0(4) . . . . ?
C22 O1 C21 C23 -174.9(3) . . . . ?
C21 O1 C22 O2 -178.2(3) . . . . ?
C21 O1 C22 C5 1.4(4) . . . . ?
C6 C5 C22 O2 177.4(4) . . . . ?
P1 C5 C22 O2 -7.7(7) . . . . ?
C6 C5 C22 O1 -2.2(4) . . . . ?
P1 C5 C22 O1 172.7(3) . . . . ?
C6 C21 C23 C28 -2.5(7) . . . . ?
O1 C21 C23 C28 170.7(3) . . . . ?
C6 C21 C23 C24 -177.8(4) . . . . ?
O1 C21 C23 C24 -4.6(5) . . . . ?
C28 C23 C24 C25 -5.1(6) . . . . ?
C21 C23 C24 C25 170.4(4) . . . . ?
C23 C24 C25 C26 0.8(6) . . . . ?
C24 C25 C26 C27 3.9(6) . . . . ?
C24 C25 C26 N1 -173.1(3) . . . . ?
O3 N1 C26 C25 4.5(5) . . . . ?
O4 N1 C26 C25 -177.3(3) . . . . ?
O3 N1 C26 C27 -172.6(3) . . . . ?
O4 N1 C26 C27 5.6(5) . . . . ?
C25 C26 C27 C28 -4.1(6) . . . . ?
N1 C26 C27 C28 173.0(3) . . . . ?
C26 C27 C28 C23 -0.5(6) . . . . ?
C24 C23 C28 C27 4.9(6) . . . . ?
C21 C23 C28 C27 -170.5(4) . . . . ?
C12 C11 C29 C30 -0.4(7) . . . . ?
C10 C11 C29 C30 179.1(4) . . . . ?
C13 C14 C30 C29 1.9(8) . . . . ?
C11 C29 C30 C14 -1.1(7) . . . . ?
C2 C1 C31 C32 0.2(7) . . . . ?
F1 C1 C31 C32 -179.8(4) . . . . ?
C3 C4 C32 C31 0.4(7) . . . . ?
P1 C4 C32 C31 174.3(3) . . . . ?
C1 C31 C32 C4 -0.3(7) . . . . ?
C5 P1 C33 C34 156.6(3) . . . . ?
C18 P1 C33 C34 34.7(4) . . . . ?
C4 P1 C33 C34 -80.2(4) . . . . ?
C5 P1 C33 C38 -26.6(4) . . . . ?
C18 P1 C33 C38 -148.6(3) . . . . ?
C4 P1 C33 C38 96.5(3) . . . . ?
C38 C33 C34 C35 1.0(6) . . . . ?
P1 C33 C34 C35 177.7(3) . . . . ?
C33 C34 C35 C36 -0.1(6) . . . . ?
C34 C35 C36 C37 -1.1(7) . . . . ?
C34 C35 C36 F3 178.9(4) . . . . ?
F3 C36 C37 C38 -178.7(4) . . . . ?
C35 C36 C37 C38 1.3(7) . . . . ?
C36 C37 C38 C33 -0.3(6) . . . . ?
C34 C33 C38 C37 -0.8(6) . . . . ?
P1 C33 C38 C37 -177.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.710
_refine_diff_density_min         -1.188
_refine_diff_density_rms         0.081


_database_code_depnum_ccdc_archive 'CCDC 901985'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a12537a
#TrackingRef 'a12537a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H24 N O4 P'
_chemical_formula_sum            'C40 H24 N O4 P'
_chemical_formula_weight         613.57

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9693(10)
_cell_length_b                   10.0382(10)
_cell_length_c                   17.310(2)
_cell_angle_alpha                79.783(7)
_cell_angle_beta                 89.864(6)
_cell_angle_gamma                66.349(6)
_cell_volume                     1557.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            red(dark)
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9127
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12000
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.20
_diffrn_reflns_theta_max         24.96
_reflns_number_total             5216
_reflns_number_gt                3786
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0986P)²+0.8133P] 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         5216
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1871
_refine_ls_wR_factor_gt          0.1657
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.004
_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
C1 C 0.2440(4) 0.1123(4) 0.0023(2) 0.0509(10) Uani 1 1 d . . .
C2 C 0.2149(4) 0.0229(4) 0.0628(2) 0.0553(10) Uani 1 1 d . . .
H2 H 0.1400 -0.0109 0.0560 0.066 Uiso 1 1 calc R . .
C3 C 0.2965(4) -0.0177(4) 0.1340(2) 0.0490(9) Uani 1 1 d . . .
H3 H 0.2775 -0.0803 0.1766 0.059 Uiso 1 1 calc R . .
C4 C 0.4067(3) 0.0320(3) 0.1444(2) 0.0380(8) Uani 1 1 d . . .
C5 C 0.4334(4) 0.1225(4) 0.0812(2) 0.0454(9) Uani 1 1 d . . .
H5 H 0.5087 0.1560 0.0869 0.055 Uiso 1 1 calc R . .
C6 C 0.3509(4) 0.1640(4) 0.0101(2) 0.0531(10) Uani 1 1 d . . .
H6 H 0.3679 0.2274 -0.0328 0.064 Uiso 1 1 calc R . .
C7 C 0.4901(3) -0.0120(3) 0.22020(19) 0.0336(7) Uani 1 1 d . . .
C8 C 0.6030(3) 0.0150(3) 0.24859(19) 0.0325(7) Uani 1 1 d . . .
C9 C 0.6407(3) -0.0639(3) 0.32975(18) 0.0292(7) Uani 1 1 d . . .
C10 C 0.5458(3) -0.1367(3) 0.34718(19) 0.0310(7) Uani 1 1 d . . .
C11 C 0.7357(3) 0.1287(3) 0.39732(18) 0.0294(7) Uani 1 1 d . . .
C12 C 0.5975(3) 0.2159(3) 0.4176(2) 0.0379(8) Uani 1 1 d . . .
H12 H 0.5285 0.1737 0.4308 0.045 Uiso 1 1 calc R . .
C13 C 0.5599(4) 0.3637(4) 0.4187(2) 0.0454(9) Uani 1 1 d . . .
H13 H 0.4658 0.4226 0.4335 0.054 Uiso 1 1 calc R . .
C14 C 0.6591(4) 0.4257(4) 0.3983(2) 0.0509(10) Uani 1 1 d . . .
H14 H 0.6330 0.5276 0.3987 0.061 Uiso 1 1 calc R . .
C15 C 0.7958(4) 0.3400(4) 0.3774(2) 0.0494(10) Uani 1 1 d . . .
H15 H 0.8637 0.3834 0.3636 0.059 Uiso 1 1 calc R . .
C16 C 0.8357(4) 0.1916(3) 0.3763(2) 0.0380(8) Uani 1 1 d . . .
H16 H 0.9299 0.1333 0.3614 0.046 Uiso 1 1 calc R . .
C17 C 0.9555(3) -0.1479(3) 0.35962(18) 0.0277(7) Uani 1 1 d . . .
C18 C 0.9755(3) -0.1981(3) 0.28880(19) 0.0337(7) Uani 1 1 d . . .
H18 H 0.8930 -0.1870 0.2568 0.040 Uiso 1 1 calc R . .
C19 C 1.1156(4) -0.2643(4) 0.2652(2) 0.0398(8) Uani 1 1 d . . .
H19 H 1.1292 -0.2972 0.2164 0.048 Uiso 1 1 calc R . .
C20 C 1.2352(4) -0.2827(4) 0.3119(2) 0.0405(8) Uani 1 1 d . . .
H20 H 1.3312 -0.3282 0.2951 0.049 Uiso 1 1 calc R . .
C21 C 1.2170(3) -0.2356(3) 0.3829(2) 0.0373(8) Uani 1 1 d . . .
H21 H 1.3003 -0.2497 0.4152 0.045 Uiso 1 1 calc R . .
C22 C 1.0780(3) -0.1683(3) 0.40711(19) 0.0332(7) Uani 1 1 d . . .
H22 H 1.0654 -0.1359 0.4560 0.040 Uiso 1 1 calc R . .
C23 C 0.7807(3) -0.1654(3) 0.48935(18) 0.0276(7) Uani 1 1 d . . .
C24 C 0.8242(3) -0.3178(3) 0.4977(2) 0.0354(8) Uani 1 1 d . . .
H24 H 0.8412 -0.3623 0.4525 0.042 Uiso 1 1 calc R . .
C25 C 0.8427(4) -0.4043(4) 0.5716(2) 0.0424(9) Uani 1 1 d . . .
H25 H 0.8716 -0.5081 0.5772 0.051 Uiso 1 1 calc R . .
C26 C 0.8193(4) -0.3401(4) 0.6378(2) 0.0475(9) Uani 1 1 d . . .
H26 H 0.8341 -0.4003 0.6886 0.057 Uiso 1 1 calc R . .
C27 C 0.7747(4) -0.1893(4) 0.6301(2) 0.0466(9) Uani 1 1 d . . .
H27 H 0.7572 -0.1455 0.6755 0.056 Uiso 1 1 calc R . .
C28 C 0.7552(3) -0.1014(3) 0.55599(19) 0.0351(8) Uani 1 1 d . . .
H28 H 0.7245 0.0027 0.5507 0.042 Uiso 1 1 calc R . .
C29 C 0.6779(3) 0.0987(4) 0.2099(2) 0.0383(8) Uani 1 1 d . . .
C30 C 0.7564(4) 0.1604(4) 0.1887(2) 0.0464(9) Uani 1 1 d . . .
C31 C 0.8498(4) 0.2292(4) 0.1691(2) 0.0548(10) Uani 1 1 d . . .
C32 C 0.9343(5) 0.2876(5) 0.1567(3) 0.0615(11) Uani 1 1 d . . .
C33 C 1.0315(5) 0.3523(5) 0.1436(3) 0.0664(12) Uani 1 1 d . . .
C34 C 1.1221(5) 0.4016(5) 0.1357(3) 0.0680(12) Uani 1 1 d . . .
C35 C 1.2253(5) 0.4682(5) 0.1209(3) 0.0662(13) Uani 1 1 d . . .
C36 C 1.2073(7) 0.5740(6) 0.0553(4) 0.0957(18) Uani 1 1 d . . .
H36 H 1.1260 0.6040 0.0180 0.115 Uiso 1 1 calc R . .
C37 C 1.3095(8) 0.6386(8) 0.0431(4) 0.1171(15) Uani 1 1 d . . .
H37 H 1.2965 0.7121 -0.0026 0.141 Uiso 1 1 calc R . .
C38 C 1.4272(8) 0.5967(7) 0.0961(4) 0.114(2) Uani 1 1 d . . .
H38 H 1.4964 0.6397 0.0867 0.137 Uiso 1 1 calc R . .
C39 C 1.4456(6) 0.4922(6) 0.1633(4) 0.0929(12) Uani 1 1 d . . .
H39 H 1.5249 0.4656 0.2014 0.111 Uiso 1 1 calc R . .
C40 C 1.3460(5) 0.4259(5) 0.1744(3) 0.0777(15) Uani 1 1 d . . .
H40 H 1.3608 0.3504 0.2193 0.093 Uiso 1 1 calc R . .
N1 N 0.1589(4) 0.1551(5) -0.0744(2) 0.0676(10) Uani 1 1 d . . .
O1 O 0.1860(4) 0.2370(4) -0.1274(2) 0.0977(12) Uani 1 1 d . . .
O2 O 0.0664(4) 0.1071(4) -0.0811(2) 0.0953(12) Uani 1 1 d . . .
O3 O 0.4542(2) -0.1025(2) 0.27801(13) 0.0370(6) Uani 1 1 d . . .
O4 O 0.5284(2) -0.2151(2) 0.40545(14) 0.0406(6) Uani 1 1 d . . .
P1 P 0.77388(8) -0.06116(8) 0.39236(5) 0.0269(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.364(5) . ?
C1 C6 1.375(5) . ?
C1 N1 1.475(5) . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 C7 1.453(4) . ?
C5 C6 1.383(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.369(4) . ?
C7 O3 1.375(4) . ?
C8 C29 1.419(4) . ?
C8 C9 1.453(4) . ?
C9 C10 1.412(4) . ?
C9 P1 1.728(3) . ?
C10 O4 1.222(4) . ?
C10 O3 1.412(4) . ?
C11 C12 1.388(4) . ?
C11 C16 1.396(4) . ?
C11 P1 1.805(3) . ?
C12 C13 1.380(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.391(4) . ?
C17 C22 1.398(4) . ?
C17 P1 1.806(3) . ?
C18 C19 1.381(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.373(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.392(4) . ?
C23 C28 1.392(4) . ?
C23 P1 1.800(3) . ?
C24 C25 1.379(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.387(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.200(4) . ?
C30 C31 1.374(5) . ?
C31 C32 1.205(5) . ?
C32 C33 1.365(5) . ?
C33 C34 1.189(5) . ?
C34 C35 1.435(6) . ?
C35 C36 1.368(7) . ?
C35 C40 1.393(7) . ?
C36 C37 1.407(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.367(9) . ?
C37 H37 0.9500 . ?
C38 C39 1.378(8) . ?
C38 H38 0.9500 . ?
C39 C40 1.397(6) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
N1 O2 1.214(5) . ?
N1 O1 1.225(5) . ?

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
C2 C1 C6 122.2(3) . . ?
C2 C1 N1 119.2(4) . . ?
C6 C1 N1 118.6(4) . . ?
C1 C2 C3 118.7(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 C7 121.8(3) . . ?
C3 C4 C7 119.6(3) . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1 C6 C5 119.1(4) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 O3 109.7(3) . . ?
C8 C7 C4 133.9(3) . . ?
O3 C7 C4 116.4(3) . . ?
C7 C8 C29 129.6(3) . . ?
C7 C8 C9 107.1(3) . . ?
C29 C8 C9 123.2(3) . . ?
C10 C9 C8 107.3(3) . . ?
C10 C9 P1 127.6(2) . . ?
C8 C9 P1 125.1(2) . . ?
O4 C10 O3 118.7(2) . . ?
O4 C10 C9 134.9(3) . . ?
O3 C10 C9 106.4(3) . . ?
C12 C11 C16 119.8(3) . . ?
C12 C11 P1 117.8(2) . . ?
C16 C11 P1 122.3(2) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 119.1(3) . . ?
C15 C16 H16 120.5 . . ?
C11 C16 H16 120.5 . . ?
C18 C17 C22 119.5(3) . . ?
C18 C17 P1 121.0(2) . . ?
C22 C17 P1 119.5(2) . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C17 119.9(3) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C24 C23 C28 119.5(3) . . ?
C24 C23 P1 117.8(2) . . ?
C28 C23 P1 122.5(2) . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 120.0(3) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C23 120.1(3) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C30 C29 C8 168.9(3) . . ?
C29 C30 C31 176.4(4) . . ?
C32 C31 C30 176.1(5) . . ?
C31 C32 C33 179.1(5) . . ?
C34 C33 C32 175.9(6) . . ?
C33 C34 C35 175.8(6) . . ?
C36 C35 C40 118.8(4) . . ?
C36 C35 C34 121.4(5) . . ?
C40 C35 C34 119.9(5) . . ?
C35 C36 C37 120.0(6) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C38 C37 C36 120.8(6) . . ?
C38 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C37 C38 C39 120.1(5) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C38 C39 C40 119.0(6) . . ?
C38 C39 H39 120.5 . . ?
C40 C39 H39 120.5 . . ?
C39 C40 C35 121.4(5) . . ?
C39 C40 H40 119.3 . . ?
C35 C40 H40 119.3 . . ?
O2 N1 O1 124.0(4) . . ?
O2 N1 C1 118.1(4) . . ?
O1 N1 C1 117.9(4) . . ?
C7 O3 C10 109.5(2) . . ?
C9 P1 C23 111.43(14) . . ?
C9 P1 C11 109.03(14) . . ?
C23 P1 C11 110.06(14) . . ?
C9 P1 C17 111.71(14) . . ?
C23 P1 C17 105.13(13) . . ?
C11 P1 C17 109.43(13) . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        24.96
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.059


_database_code_depnum_ccdc_archive 'CCDC 902919'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_12933
#TrackingRef '12933.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H24 N O4 P'
_chemical_formula_sum            'C42 H24 N O4 P'
_chemical_formula_weight         637.59

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2329(2)
_cell_length_b                   10.2980(2)
_cell_length_c                   17.3524(5)
_cell_angle_alpha                97.5580(10)
_cell_angle_beta                 92.4750(10)
_cell_angle_gamma                116.5570(10)
_cell_volume                     1610.66(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    13791
_cell_measurement_theta_min      2.037
_cell_measurement_theta_max      25.028

_exptl_crystal_description       prism
_exptl_crystal_colour            green-brown(dark)
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8327
_exptl_absorpt_correction_T_max  1.1733
_exptl_absorpt_process_details   
;
?
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17911
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_sigmaI/netI    0.0783
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.08
_reflns_number_total             5696
_reflns_number_gt                3779
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1083P)²+0.2013P] 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         5696
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.2040
_refine_ls_wR_factor_gt          0.1591
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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
C1 C 0.9453(4) 1.1633(3) 0.36797(19) 0.0272(8) Uani 1 1 d . . .
C2 C 0.9665(4) 1.2089(4) 0.2955(2) 0.0345(8) Uani 1 1 d . . .
H2 H 0.8855 1.1999 0.2623 0.041 Uiso 1 1 calc R . .
C3 C 1.1057(4) 1.2673(4) 0.2719(2) 0.0392(9) Uani 1 1 d . . .
H3 H 1.1200 1.2985 0.2224 0.047 Uiso 1 1 calc R . .
C4 C 1.2230(4) 1.2805(4) 0.3190(2) 0.0407(9) Uani 1 1 d . . .
H4 H 1.3178 1.3186 0.3015 0.049 Uiso 1 1 calc R . .
C5 C 1.2047(4) 1.2390(4) 0.3918(2) 0.0399(9) Uani 1 1 d . . .
H5 H 1.2871 1.2507 0.4248 0.048 Uiso 1 1 calc R . .
C6 C 1.0675(4) 1.1809(4) 0.4165(2) 0.0334(8) Uani 1 1 d . . .
H6 H 1.0551 1.1523 0.4666 0.040 Uiso 1 1 calc R . .
C7 C 0.7197(4) 0.8867(3) 0.40114(19) 0.0288(8) Uani 1 1 d . . .
C8 C 0.8151(4) 0.8282(4) 0.3811(2) 0.0357(9) Uani 1 1 d . . .
H8 H 0.9097 0.8898 0.3678 0.043 Uiso 1 1 calc R . .
C9 C 0.7719(5) 0.6800(4) 0.3807(2) 0.0438(10) Uani 1 1 d . . .
H9 H 0.8369 0.6402 0.3665 0.053 Uiso 1 1 calc R . .
C10 C 0.6353(5) 0.5896(4) 0.4007(2) 0.0455(10) Uani 1 1 d . . .
H10 H 0.6070 0.4885 0.4012 0.055 Uiso 1 1 calc R . .
C11 C 0.5399(5) 0.6469(4) 0.4199(2) 0.0444(10) Uani 1 1 d . . .
H11 H 0.4456 0.5846 0.4334 0.053 Uiso 1 1 calc R . .
C12 C 0.5801(4) 0.7937(4) 0.4198(2) 0.0374(9) Uani 1 1 d . . .
H12 H 0.5131 0.8318 0.4325 0.045 Uiso 1 1 calc R . .
C13 C 0.7813(4) 1.1711(4) 0.49718(19) 0.0288(8) Uani 1 1 d . . .
C14 C 0.7616(4) 1.1014(4) 0.5620(2) 0.0362(9) Uani 1 1 d . . .
H14 H 0.7304 0.9983 0.5552 0.043 Uiso 1 1 calc R . .
C15 C 0.7871(5) 1.1809(4) 0.6364(2) 0.0469(10) Uani 1 1 d . . .
H15 H 0.7750 1.1328 0.6806 0.056 Uiso 1 1 calc R . .
C16 C 0.8305(4) 1.3310(4) 0.6465(2) 0.0478(10) Uani 1 1 d . . .
H16 H 0.8469 1.3855 0.6976 0.057 Uiso 1 1 calc R . .
C17 C 0.8498(4) 1.4008(4) 0.5826(2) 0.0435(10) Uani 1 1 d . . .
H17 H 0.8797 1.5036 0.5897 0.052 Uiso 1 1 calc R . .
C18 C 0.8259(4) 1.3223(4) 0.5081(2) 0.0365(9) Uani 1 1 d . . .
H18 H 0.8398 1.3713 0.4641 0.044 Uiso 1 1 calc R . .
C19 C 0.6324(4) 1.0848(3) 0.33771(19) 0.0273(8) Uani 1 1 d . . .
C20 C 0.5423(4) 1.1550(4) 0.3538(2) 0.0298(8) Uani 1 1 d . . .
C21 C 0.4735(4) 1.0316(4) 0.2286(2) 0.0321(8) Uani 1 1 d . . .
C22 C 0.3851(4) 0.9846(4) 0.1536(2) 0.0375(9) Uani 1 1 d . . .
C23 C 0.2711(5) 1.0206(5) 0.1399(2) 0.0500(11) Uani 1 1 d . . .
H23 H 0.2505 1.0777 0.1806 0.060 Uiso 1 1 calc R . .
C24 C 0.1882(5) 0.9746(5) 0.0682(3) 0.0537(11) Uani 1 1 d . . .
H24 H 0.1100 0.9988 0.0596 0.064 Uiso 1 1 calc R . .
C25 C 0.2185(4) 0.8942(4) 0.0097(2) 0.0439(10) Uani 1 1 d . . .
C26 C 0.3274(6) 0.8565(7) 0.0213(3) 0.0872(19) Uani 1 1 d . . .
H26 H 0.3464 0.7988 -0.0198 0.105 Uiso 1 1 calc R . .
C27 C 0.4099(6) 0.9019(7) 0.0923(3) 0.0834(18) Uani 1 1 d . . .
H27 H 0.4869 0.8757 0.0998 0.100 Uiso 1 1 calc R . .
C28 C 0.5854(4) 1.0064(4) 0.2576(2) 0.0323(8) Uani 1 1 d . . .
C29 C 0.6495(4) 0.9229(4) 0.2191(2) 0.0369(9) Uani 1 1 d . . .
C30 C 0.7192(4) 0.8612(4) 0.1944(2) 0.0396(9) Uani 1 1 d . . .
C31 C 0.8020(5) 0.7938(4) 0.1713(2) 0.0476(10) Uani 1 1 d . . .
C32 C 0.8763(5) 0.7331(5) 0.1554(3) 0.0526(11) Uani 1 1 d . . .
C33 C 0.9607(5) 0.6633(5) 0.1407(3) 0.0596(12) Uani 1 1 d . . .
C34 C 1.0396(6) 0.6058(5) 0.1307(3) 0.0639(13) Uani 1 1 d . . .
C35 C 1.1351(6) 0.5479(5) 0.1216(3) 0.0649(14) Uani 1 1 d . . .
C36 C 1.2258(5) 0.5040(5) 0.1172(3) 0.0619(13) Uani 1 1 d . . .
C37 C 1.3372(5) 0.4563(4) 0.1161(3) 0.0515(11) Uani 1 1 d . . .
C38 C 1.3483(6) 0.3725(6) 0.0509(3) 0.0691(14) Uani 1 1 d . . .
H38 H 1.2805 0.3440 0.0053 0.083 Uiso 1 1 calc R . .
C39 C 1.4579(6) 0.3295(6) 0.0516(3) 0.0843(18) Uani 1 1 d . . .
H39 H 1.4673 0.2737 0.0060 0.101 Uiso 1 1 calc R . .
C40 C 1.5539(6) 0.3678(5) 0.1184(3) 0.0696(14) Uani 1 1 d . . .
H40 H 1.6282 0.3364 0.1190 0.084 Uiso 1 1 calc R . .
C41 C 1.5433(5) 0.4489(5) 0.1827(3) 0.0680(13) Uani 1 1 d . . .
H41 H 1.6097 0.4744 0.2286 0.082 Uiso 1 1 calc R . .
C42 C 1.4365(5) 0.4953(5) 0.1824(3) 0.0642(13) Uani 1 1 d . . .
H42 H 1.4306 0.5543 0.2278 0.077 Uiso 1 1 calc R . .
N1 N 0.1331(4) 0.8442(4) -0.0677(2) 0.0542(9) Uani 1 1 d . . .
O1 O 0.1687(4) 0.7780(4) -0.12021(18) 0.0692(9) Uani 1 1 d . . .
O2 O 0.0288(4) 0.8701(4) -0.0768(2) 0.0883(12) Uani 1 1 d . . .
O3 O 0.4460(2) 1.1206(2) 0.28467(13) 0.0340(6) Uani 1 1 d . . .
O4 O 0.5333(3) 1.2337(3) 0.41058(14) 0.0395(6) Uani 1 1 d . . .
P1 P 0.76476(10) 1.07703(9) 0.39925(5) 0.0272(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.392(5) . ?
C1 C6 1.404(5) . ?
C1 P1 1.801(3) . ?
C2 C3 1.381(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.371(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.392(5) . ?
C7 C12 1.401(5) . ?
C7 P1 1.807(3) . ?
C8 C9 1.385(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.387(5) . ?
C13 C18 1.397(4) . ?
C13 P1 1.803(3) . ?
C14 C15 1.381(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.420(5) . ?
C19 C28 1.455(5) . ?
C19 P1 1.725(3) . ?
C20 O4 1.224(4) . ?
C20 O3 1.418(4) . ?
C21 C28 1.371(5) . ?
C21 O3 1.374(4) . ?
C21 C22 1.444(5) . ?
C22 C27 1.377(5) . ?
C22 C23 1.394(5) . ?
C23 C24 1.373(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.360(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.349(6) . ?
C25 N1 1.466(5) . ?
C26 C27 1.363(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.417(5) . ?
C29 C30 1.207(5) . ?
C30 C31 1.357(5) . ?
C31 C32 1.200(5) . ?
C32 C33 1.362(6) . ?
C33 C34 1.202(5) . ?
C34 C35 1.358(6) . ?
C35 C36 1.201(6) . ?
C36 C37 1.428(6) . ?
C37 C38 1.372(6) . ?
C37 C42 1.390(7) . ?
C38 C39 1.377(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.379(7) . ?
C39 H39 0.9500 . ?
C40 C41 1.342(6) . ?
C40 H40 0.9500 . ?
C41 C42 1.374(6) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
N1 O2 1.219(4) . ?
N1 O1 1.231(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.9(3) . . ?
C2 C1 P1 121.6(3) . . ?
C6 C1 P1 119.5(3) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C8 C7 C12 119.2(3) . . ?
C8 C7 P1 122.6(3) . . ?
C12 C7 P1 118.2(2) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C14 C13 C18 119.2(3) . . ?
C14 C13 P1 122.6(3) . . ?
C18 C13 P1 118.1(3) . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.0(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.0(4) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.1(3) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C20 C19 C28 106.7(3) . . ?
C20 C19 P1 129.3(3) . . ?
C28 C19 P1 123.8(2) . . ?
O4 C20 O3 118.4(3) . . ?
O4 C20 C19 134.9(3) . . ?
O3 C20 C19 106.7(3) . . ?
C28 C21 O3 109.9(3) . . ?
C28 C21 C22 133.0(3) . . ?
O3 C21 C22 117.1(3) . . ?
C27 C22 C23 117.0(4) . . ?
C27 C22 C21 121.4(4) . . ?
C23 C22 C21 121.6(3) . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 119.7(4) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 121.0(4) . . ?
C26 C25 N1 117.8(4) . . ?
C24 C25 N1 121.2(4) . . ?
C25 C26 C27 119.5(4) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C26 C27 C22 122.1(4) . . ?
C26 C27 H27 118.9 . . ?
C22 C27 H27 118.9 . . ?
C21 C28 C29 128.4(3) . . ?
C21 C28 C19 107.4(3) . . ?
C29 C28 C19 124.1(3) . . ?
C30 C29 C28 171.2(4) . . ?
C29 C30 C31 176.3(4) . . ?
C32 C31 C30 176.1(4) . . ?
C31 C32 C33 177.5(5) . . ?
C34 C33 C32 177.0(6) . . ?
C33 C34 C35 176.8(6) . . ?
C36 C35 C34 175.8(6) . . ?
C35 C36 C37 176.9(6) . . ?
C38 C37 C42 119.1(4) . . ?
C38 C37 C36 121.4(5) . . ?
C42 C37 C36 119.6(4) . . ?
C37 C38 C39 119.9(5) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C38 C39 C40 119.9(5) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C41 C40 C39 120.6(5) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C40 C41 C42 120.1(5) . . ?
C40 C41 H41 119.9 . . ?
C42 C41 H41 119.9 . . ?
C41 C42 C37 120.3(4) . . ?
C41 C42 H42 119.8 . . ?
C37 C42 H42 119.8 . . ?
O2 N1 O1 123.0(4) . . ?
O2 N1 C25 117.8(4) . . ?
O1 N1 C25 119.2(4) . . ?
C21 O3 C20 109.1(2) . . ?
C19 P1 C1 112.64(15) . . ?
C19 P1 C13 111.91(15) . . ?
C1 P1 C13 105.68(15) . . ?
C19 P1 C7 109.34(15) . . ?
C1 P1 C7 107.29(15) . . ?
C13 P1 C7 109.82(15) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.117


_database_code_depnum_ccdc_archive 'CCDC 903961'
