# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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.
#
data_avv19
_audit_creation_date             2014-04-02
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H17 O P, 0.5(H2 O)'
_chemical_formula_sum            'C17 H18 O1.50 P'
_chemical_formula_weight         277.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c17 h20 o1 p1'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.2780(11)
_cell_length_b                   7.9874(3)
_cell_length_c                   14.5933(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.398(4)
_cell_angle_gamma                90.00
_cell_volume                     2937.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2687
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3260
_cell_measurement_theta_min      2.9780
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9976
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.68
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.8707
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -94.00  -68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   19.0000 -180.0000 109

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   57.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -94.00  -43.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  178.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
  7 omega  -23.00    2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  -30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0053547000
_diffrn_orient_matrix_UB_12      -0.0829738000
_diffrn_orient_matrix_UB_13      -0.0139870000
_diffrn_orient_matrix_UB_21      0.0200081000
_diffrn_orient_matrix_UB_22      0.0303607000
_diffrn_orient_matrix_UB_23      -0.0271659000
_diffrn_orient_matrix_UB_31      0.0190550000
_diffrn_orient_matrix_UB_32      -0.0086897000
_diffrn_orient_matrix_UB_33      0.0379975000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2637
_reflns_number_total             3278
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0351P)²+3.1917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1023
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.108414(18) 0.23105(6) 0.62318(3) 0.01416(13) Uani 1 1 d . . .
O19 O 0.08572(5) 0.25958(16) 0.71311(8) 0.0207(3) Uani 1 1 d . . .
C9 C 0.11611(7) 0.4169(2) 0.55744(11) 0.0143(4) Uani 1 1 d . . .
C11 C 0.17311(7) 0.1348(2) 0.64150(11) 0.0142(4) Uani 1 1 d . . .
C3 C 0.05725(7) 0.1387(2) 0.45965(12) 0.0197(4) Uani 1 1 d . . .
H3 H 0.0398 0.0554 0.4245 0.024 Uiso 1 1 calc R . .
C16 C 0.18675(7) 0.0607(2) 0.72695(12) 0.0181(4) Uani 1 1 d . . .
H16 H 0.1640 0.0692 0.7739 0.022 Uiso 1 1 calc R . .
C14 C 0.26847(8) -0.0377(2) 0.67211(13) 0.0218(4) Uani 1 1 d . . .
H14 H 0.3003 -0.0957 0.6822 0.026 Uiso 1 1 calc R . .
C10 C 0.09476(7) 0.4374(2) 0.46664(11) 0.0157(4) Uani 1 1 d . . .
C6 C 0.12909(8) 0.7213(2) 0.47098(13) 0.0249(4) Uani 1 1 d . . .
H6 H 0.1332 0.8232 0.4415 0.030 Uiso 1 1 calc R . .
C4 C 0.06467(7) 0.3015(2) 0.41058(11) 0.0180(4) Uani 1 1 d . . .
C7 C 0.15030(8) 0.7002(2) 0.56121(13) 0.0238(4) Uani 1 1 d . . .
H7 H 0.1688 0.7866 0.5921 0.029 Uiso 1 1 calc R . .
C5 C 0.10206(8) 0.5932(2) 0.42492(12) 0.0209(4) Uani 1 1 d . . .
H5 H 0.0883 0.6103 0.3647 0.025 Uiso 1 1 calc R . .
C15 C 0.23448(8) -0.0259(2) 0.74141(13) 0.0220(4) Uani 1 1 d . . .
H15 H 0.2435 -0.0760 0.7980 0.026 Uiso 1 1 calc R . .
C2 C 0.07188(7) 0.0967(2) 0.54551(12) 0.0183(4) Uani 1 1 d . . .
H2 H 0.0625 -0.0086 0.5661 0.022 Uiso 1 1 calc R . .
C12 C 0.20764(7) 0.1214(2) 0.57211(12) 0.0173(4) Uani 1 1 d . . .
H12 H 0.1986 0.1697 0.5151 0.021 Uiso 1 1 calc R . .
C13 C 0.25534(7) 0.0367(2) 0.58734(13) 0.0204(4) Uani 1 1 d . . .
H13 H 0.2785 0.0297 0.5410 0.025 Uiso 1 1 calc R . .
C17 C 0.00817(7) 0.3640(3) 0.37920(13) 0.0263(5) Uani 1 1 d . . .
H17A H -0.0100 0.2802 0.3415 0.039 Uiso 1 1 calc R . .
H17B H 0.0106 0.4655 0.3445 0.039 Uiso 1 1 calc R . .
H17C H -0.0112 0.3851 0.4321 0.039 Uiso 1 1 calc R . .
C8 C 0.14335(7) 0.5487(2) 0.60376(12) 0.0175(4) Uani 1 1 d . . .
H8 H 0.1569 0.5335 0.6642 0.021 Uiso 1 1 calc R . .
C18 C 0.09491(8) 0.2627(3) 0.32474(12) 0.0251(5) Uani 1 1 d . . .
H18A H 0.1306 0.2297 0.3437 0.038 Uiso 1 1 calc R . .
H18B H 0.0955 0.3609 0.2869 0.038 Uiso 1 1 calc R . .
H18C H 0.0774 0.1735 0.2904 0.038 Uiso 1 1 calc R . .
O20 O 0.0000 0.0528(3) 0.7500 0.0299(5) Uani 1 2 d SG . .
H20A H 0.0253 0.1167 0.7377 0.045 Uiso 0.50 1 d PG . .
H20B H -0.0286 0.1091 0.7491 0.045 Uiso 0.50 1 d PG . .


_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 O19 1.4895(13) . ?
P1 C9 1.7863(18) . ?
P1 C11 1.8084(18) . ?
P1 C2 1.7687(17) . ?
C9 C10 1.401(2) . ?
C9 C8 1.403(2) . ?
C11 C16 1.399(2) . ?
C11 C12 1.391(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.503(3) . ?
C3 C2 1.322(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.393(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(3) . ?
C14 C13 1.390(3) . ?
C10 C4 1.527(2) . ?
C10 C5 1.404(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.393(3) . ?
C6 C5 1.377(3) . ?
C4 C17 1.549(2) . ?
C4 C18 1.548(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(3) . ?
C5 H5 0.9300 . ?
C15 H15 0.9300 . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8 H8 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O20 H20A 0.8490 . ?
O20 H20B 0.8509 . ?

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
O19 P1 C9 114.28(8) . . ?
O19 P1 C11 109.87(8) . . ?
O19 P1 C2 116.10(8) . . ?
C9 P1 C11 107.36(8) . . ?
C2 P1 C9 103.48(8) . . ?
C2 P1 C11 104.99(8) . . ?
C10 C9 P1 123.71(14) . . ?
C10 C9 C8 120.48(16) . . ?
C8 C9 P1 115.75(12) . . ?
C16 C11 P1 118.03(14) . . ?
C12 C11 P1 122.40(13) . . ?
C12 C11 C16 119.40(16) . . ?
C4 C3 H3 115.3 . . ?
C2 C3 H3 115.3 . . ?
C2 C3 C4 129.41(16) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.77(18) . . ?
C15 C16 H16 120.1 . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.25(17) . . ?
C13 C14 H14 119.9 . . ?
C9 C10 C4 124.30(16) . . ?
C9 C10 C5 117.38(16) . . ?
C5 C10 C4 118.32(15) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.79(18) . . ?
C3 C4 C10 115.78(14) . . ?
C3 C4 C17 105.90(16) . . ?
C3 C4 C18 107.46(15) . . ?
C10 C4 C17 109.84(15) . . ?
C10 C4 C18 108.61(15) . . ?
C18 C4 C17 109.07(14) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 C6 118.64(18) . . ?
C8 C7 H7 120.7 . . ?
C10 C5 H5 119.2 . . ?
C6 C5 C10 121.60(16) . . ?
C6 C5 H5 119.2 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.26(16) . . ?
C14 C15 H15 119.9 . . ?
P1 C2 H2 118.4 . . ?
C3 C2 P1 123.21(15) . . ?
C3 C2 H2 118.4 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.51(16) . . ?
C13 C12 H12 119.7 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 C14 119.81(18) . . ?
C12 C13 H13 120.1 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C8 H8 119.4 . . ?
C7 C8 C9 121.12(16) . . ?
C7 C8 H8 119.4 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H20A O20 H20B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C9 C10 C4 -3.2(3) . . . . ?
P1 C9 C10 C5 177.27(14) . . . . ?
P1 C9 C8 C7 -177.91(15) . . . . ?
P1 C11 C16 C15 175.08(14) . . . . ?
P1 C11 C12 C13 -175.61(14) . . . . ?
O19 P1 C9 C10 -125.52(15) . . . . ?
O19 P1 C9 C8 51.59(16) . . . . ?
O19 P1 C11 C16 16.78(16) . . . . ?
O19 P1 C11 C12 -168.01(14) . . . . ?
O19 P1 C2 C3 127.42(17) . . . . ?
C9 P1 C11 C16 141.61(14) . . . . ?
C9 P1 C11 C12 -43.19(16) . . . . ?
C9 P1 C2 C3 1.39(19) . . . . ?
C9 C10 C4 C3 1.6(3) . . . . ?
C9 C10 C4 C17 121.45(19) . . . . ?
C9 C10 C4 C18 -119.34(19) . . . . ?
C9 C10 C5 C6 0.0(3) . . . . ?
C11 P1 C9 C10 112.37(16) . . . . ?
C11 P1 C9 C8 -70.52(15) . . . . ?
C11 P1 C2 C3 -111.06(17) . . . . ?
C11 C16 C15 C14 0.5(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C16 C11 C12 C13 -0.5(3) . . . . ?
C10 C9 C8 C7 -0.7(3) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C4 C3 C2 P1 -3.3(3) . . . . ?
C4 C10 C5 C6 -179.55(17) . . . . ?
C7 C6 C5 C10 0.1(3) . . . . ?
C5 C10 C4 C3 -178.85(16) . . . . ?
C5 C10 C4 C17 -59.0(2) . . . . ?
C5 C10 C4 C18 60.2(2) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C15 C14 C13 C12 -0.7(3) . . . . ?
C2 P1 C9 C10 1.67(18) . . . . ?
C2 P1 C9 C8 178.78(14) . . . . ?
C2 P1 C11 C16 -108.73(15) . . . . ?
C2 P1 C11 C12 66.47(16) . . . . ?
C2 C3 C4 C10 1.9(3) . . . . ?
C2 C3 C4 C17 -120.1(2) . . . . ?
C2 C3 C4 C18 123.4(2) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C8 C9 C10 C4 179.83(16) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1026531'
#######################################################################
#
#                 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_avv20a
_audit_creation_date             2014-04-02
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H21 O P'
_chemical_formula_sum            'C20 H18 O P'
_chemical_formula_weight         305.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H18 o1 p1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0477(2)
_cell_length_b                   17.5321(4)
_cell_length_c                   9.9229(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.056(2)
_cell_angle_gamma                90.00
_cell_volume                     1571.78(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3767
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8780
_cell_measurement_theta_min      5.0380
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8790
_diffrn_reflns_theta_full        72.45
_diffrn_reflns_theta_max         72.45
_diffrn_reflns_theta_min         5.05
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9403
_diffrn_measured_fraction_theta_max 0.9889
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -27.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   60.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  150.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega  -37.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega  114.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  8 omega   61.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   82.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   51.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega  123.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   88.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   80.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
 14 omega  131.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 15 omega  142.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   66.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 17 omega   82.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 18 omega   82.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
 19 omega   78.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
 20 omega  104.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  120.0000 74

#__ type_ start__ end____ width___ exp.time_
 21 omega   67.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -40.0000   -6.2262 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   36.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -120.0000 68

#__ type_ start__ end____ width___ exp.time_
 23 omega   32.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1284076000
_diffrn_orient_matrix_UB_12      -0.0125675000
_diffrn_orient_matrix_UB_13      0.1060783000
_diffrn_orient_matrix_UB_21      -0.0444702000
_diffrn_orient_matrix_UB_22      0.0731825000
_diffrn_orient_matrix_UB_23      0.0736273000
_diffrn_orient_matrix_UB_31      -0.1031063000
_diffrn_orient_matrix_UB_32      -0.0469630000
_diffrn_orient_matrix_UB_33      0.0865345000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2649
_reflns_number_total             3062
_reflns_odcompleteness_completeness 94.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0491P)²+0.8219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1021
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.64874(5) 0.07056(2) 0.25717(4) 0.01721(13) Uani 1 1 d . . .
O22 O 0.69706(14) 0.02989(8) 0.13577(12) 0.0268(3) Uani 1 1 d . . .
C12 C 0.36969(19) 0.06798(9) 0.12815(17) 0.0192(3) Uani 1 1 d . . .
H12 H 0.4143 0.0393 0.0628 0.023 Uiso 1 1 calc R . .
C9 C 0.74122(17) 0.15917(10) 0.29419(16) 0.0165(3) Uani 1 1 d . . .
C8 C 0.74489(18) 0.21071(11) 0.18601(16) 0.0208(4) Uani 1 1 d . . .
H8 H 0.7066 0.1960 0.1011 0.025 Uiso 1 1 calc R . .
C16 C 0.38608(19) 0.13841(9) 0.33766(16) 0.0189(3) Uani 1 1 d . . .
H16 H 0.4418 0.1570 0.4120 0.023 Uiso 1 1 calc R . .
C10 C 0.80224(17) 0.17916(9) 0.42256(16) 0.0159(3) Uani 1 1 d . . .
C11 C 0.45393(18) 0.09480(9) 0.24029(16) 0.0169(3) Uani 1 1 d . . .
C3 C 0.74111(18) 0.04865(9) 0.52282(16) 0.0177(3) Uani 1 1 d . . .
H3 H 0.7492 0.0158 0.5964 0.021 Uiso 1 1 calc R . .
C17 C 0.71891(19) 0.16669(10) 0.65822(16) 0.0186(3) Uani 1 1 d . . .
H17A H 0.7508 0.2194 0.6658 0.022 Uiso 1 1 calc R . .
H17B H 0.6145 0.1667 0.6303 0.022 Uiso 1 1 calc R . .
C14 C 0.15189(19) 0.12687(10) 0.21143(18) 0.0229(4) Uani 1 1 d . . .
H14 H 0.0511 0.1374 0.2022 0.027 Uiso 1 1 calc R . .
C4 C 0.80632(18) 0.12702(9) 0.54653(15) 0.0159(3) Uani 1 1 d . . .
C7 C 0.80418(19) 0.28268(11) 0.20340(18) 0.0226(4) Uani 1 1 d . . .
H7 H 0.8063 0.3163 0.1311 0.027 Uiso 1 1 calc R . .
C6 C 0.86108(19) 0.30430(10) 0.33124(18) 0.0233(4) Uani 1 1 d . . .
H6 H 0.8986 0.3532 0.3452 0.028 Uiso 1 1 calc R . .
C19 C 0.9012(2) 0.12214(11) 0.84337(17) 0.0260(4) Uani 1 1 d . . .
H19A H 0.9096 0.0954 0.9290 0.031 Uiso 1 1 calc R . .
H19B H 0.9432 0.1727 0.8568 0.031 Uiso 1 1 calc R . .
C15 C 0.2358(2) 0.15392(10) 0.32328(17) 0.0208(4) Uani 1 1 d . . .
H15 H 0.1907 0.1825 0.3885 0.025 Uiso 1 1 calc R . .
C18 C 0.7382(2) 0.12920(11) 0.79712(17) 0.0224(4) Uani 1 1 d . . .
H18A H 0.6871 0.1593 0.8622 0.027 Uiso 1 1 calc R . .
H18B H 0.6936 0.0789 0.7935 0.027 Uiso 1 1 calc R . .
C5 C 0.86165(19) 0.25303(10) 0.43720(17) 0.0202(3) Uani 1 1 d . . .
H5 H 0.9027 0.2679 0.5210 0.024 Uiso 1 1 calc R . .
C20 C 0.98812(19) 0.07905(10) 0.73966(17) 0.0220(4) Uani 1 1 d . . .
H20A H 0.9532 0.0268 0.7335 0.026 Uiso 1 1 calc R . .
H20B H 1.0921 0.0781 0.7691 0.026 Uiso 1 1 calc R . .
C21 C 0.97058(18) 0.11665(10) 0.60010(16) 0.0191(3) Uani 1 1 d . . .
H21A H 1.0218 0.0858 0.5361 0.023 Uiso 1 1 calc R . .
H21B H 1.0180 0.1663 0.6044 0.023 Uiso 1 1 calc R . .
C13 C 0.2186(2) 0.08421(10) 0.11397(17) 0.0223(4) Uani 1 1 d . . .
H13 H 0.1627 0.0664 0.0391 0.027 Uiso 1 1 calc R . .
C2 C 0.67355(19) 0.01984(9) 0.41138(17) 0.0196(3) Uani 1 1 d . . .
H2 H 0.6373 -0.0297 0.4147 0.024 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 O22 1.4855(13) . ?
P1 C9 1.7933(17) . ?
P1 C11 1.8122(17) . ?
P1 C2 1.7738(17) . ?
C12 H12 0.9300 . ?
C12 C11 1.396(2) . ?
C12 C13 1.396(2) . ?
C9 C8 1.405(2) . ?
C9 C10 1.405(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.378(3) . ?
C16 H16 0.9300 . ?
C16 C11 1.399(2) . ?
C16 C15 1.387(2) . ?
C10 C4 1.532(2) . ?
C10 C5 1.407(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.509(2) . ?
C3 C2 1.334(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C4 1.559(2) . ?
C17 C18 1.529(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(3) . ?
C14 C13 1.386(3) . ?
C4 C21 1.562(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.396(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.526(2) . ?
C19 C20 1.528(3) . ?
C15 H15 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C5 H5 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.534(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C13 H13 0.9300 . ?
C2 H2 0.9300 . ?

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
O22 P1 C9 115.32(8) . . ?
O22 P1 C11 111.38(7) . . ?
O22 P1 C2 115.45(8) . . ?
C9 P1 C11 104.87(8) . . ?
C2 P1 C9 102.79(8) . . ?
C2 P1 C11 105.96(8) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C13 C12 C11 120.11(16) . . ?
C8 C9 P1 115.49(12) . . ?
C8 C9 C10 120.54(16) . . ?
C10 C9 P1 123.93(13) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 C9 121.20(16) . . ?
C7 C8 H8 119.4 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C11 120.00(15) . . ?
C9 C10 C4 124.80(15) . . ?
C9 C10 C5 116.91(15) . . ?
C5 C10 C4 118.28(14) . . ?
C12 C11 P1 118.79(13) . . ?
C12 C11 C16 119.56(15) . . ?
C16 C11 P1 121.65(12) . . ?
C4 C3 H3 115.4 . . ?
C2 C3 H3 115.4 . . ?
C2 C3 C4 129.21(15) . . ?
H17A C17 H17B 107.6 . . ?
C4 C17 H17A 108.7 . . ?
C4 C17 H17B 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C18 C17 C4 114.29(14) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.02(16) . . ?
C10 C4 C17 108.26(13) . . ?
C10 C4 C21 108.94(13) . . ?
C3 C4 C10 115.20(13) . . ?
C3 C4 C17 107.95(13) . . ?
C3 C4 C21 107.71(13) . . ?
C17 C4 C21 108.63(13) . . ?
C8 C7 H7 120.5 . . ?
C8 C7 C6 118.98(16) . . ?
C6 C7 H7 120.5 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.05(17) . . ?
C5 C6 H6 120.0 . . ?
H19A C19 H19B 108.0 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C18 C19 C20 111.19(14) . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C16 C15 C14 120.30(16) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C19 C18 C17 111.58(14) . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C10 C5 H5 118.9 . . ?
C6 C5 C10 122.27(16) . . ?
C6 C5 H5 118.9 . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C19 C20 C21 111.31(14) . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C4 C21 H21A 108.7 . . ?
C4 C21 H21B 108.7 . . ?
C20 C21 C4 114.07(14) . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.01(16) . . ?
C14 C13 H13 120.0 . . ?
P1 C2 H2 118.1 . . ?
C3 C2 P1 123.82(13) . . ?
C3 C2 H2 118.1 . . ?

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
P1 C9 C8 C7 175.78(13) . . . . ?
P1 C9 C10 C4 3.5(2) . . . . ?
P1 C9 C10 C5 -175.52(13) . . . . ?
O22 P1 C9 C8 50.87(15) . . . . ?
O22 P1 C9 C10 -131.56(14) . . . . ?
O22 P1 C11 C12 6.01(16) . . . . ?
O22 P1 C11 C16 -175.07(13) . . . . ?
O22 P1 C2 C3 129.10(16) . . . . ?
C9 P1 C11 C12 131.41(14) . . . . ?
C9 P1 C11 C16 -49.68(15) . . . . ?
C9 P1 C2 C3 2.67(18) . . . . ?
C9 C8 C7 C6 -0.1(3) . . . . ?
C9 C10 C4 C3 1.2(2) . . . . ?
C9 C10 C4 C17 -119.76(17) . . . . ?
C9 C10 C4 C21 122.28(17) . . . . ?
C9 C10 C5 C6 -0.1(2) . . . . ?
C8 C9 C10 C4 -179.00(15) . . . . ?
C8 C9 C10 C5 1.9(2) . . . . ?
C8 C7 C6 C5 2.0(3) . . . . ?
C10 C9 C8 C7 -1.9(3) . . . . ?
C10 C4 C21 C20 168.40(14) . . . . ?
C11 P1 C9 C8 -72.01(14) . . . . ?
C11 P1 C9 C10 105.56(14) . . . . ?
C11 P1 C2 C3 -107.13(16) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C11 C16 C15 C14 -0.6(3) . . . . ?
C3 C4 C21 C20 -66.01(18) . . . . ?
C17 C4 C21 C20 50.67(18) . . . . ?
C4 C10 C5 C6 -179.19(16) . . . . ?
C4 C3 C2 P1 1.6(3) . . . . ?
C4 C17 C18 C19 54.5(2) . . . . ?
C7 C6 C5 C10 -1.9(3) . . . . ?
C19 C20 C21 C4 -54.74(19) . . . . ?
C15 C16 C11 P1 -178.10(13) . . . . ?
C15 C16 C11 C12 0.8(2) . . . . ?
C15 C14 C13 C12 0.3(3) . . . . ?
C18 C17 C4 C10 -168.70(14) . . . . ?
C18 C17 C4 C3 65.98(17) . . . . ?
C18 C17 C4 C21 -50.54(18) . . . . ?
C18 C19 C20 C21 55.7(2) . . . . ?
C5 C10 C4 C3 -179.79(15) . . . . ?
C5 C10 C4 C17 59.29(19) . . . . ?
C5 C10 C4 C21 -58.67(19) . . . . ?
C20 C19 C18 C17 -55.6(2) . . . . ?
C13 C12 C11 P1 178.50(13) . . . . ?
C13 C12 C11 C16 -0.4(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C2 P1 C9 C8 177.38(13) . . . . ?
C2 P1 C9 C10 -5.05(16) . . . . ?
C2 P1 C11 C12 -120.29(14) . . . . ?
C2 P1 C11 C16 58.63(15) . . . . ?
C2 C3 C4 C10 -4.0(3) . . . . ?
C2 C3 C4 C17 117.1(2) . . . . ?
C2 C3 C4 C21 -125.76(19) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1026529'
#######################################################################
#
#                 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_exp_590
_audit_creation_date             2014-01-29
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H16 Br O P'
_chemical_formula_sum            'C17 H16 Br O P'
_chemical_formula_weight         347.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 h15 p1 br1 o1'
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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   20.4116(8)
_cell_length_b                   10.1465(4)
_cell_length_c                   15.7185(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.406(5)
_cell_angle_gamma                90.00
_cell_volume                     3088.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2579
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7960
_cell_measurement_theta_min      3.4700
_exptl_absorpt_coefficient_mu    2.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10914
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.73
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9651
_diffrn_measured_fraction_theta_max 0.8218
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   51.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777   38.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
  2 omega  -34.00   35.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777   57.0000   90.0000 69

#__ type_ start__ end____ width___ exp.time_
  3 omega  -81.00   -7.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -57.0000  -90.0000 74
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0001814000
_diffrn_orient_matrix_UB_12      -0.0457279000
_diffrn_orient_matrix_UB_13      -0.0341694000
_diffrn_orient_matrix_UB_21      -0.0321463000
_diffrn_orient_matrix_UB_22      0.0255256000
_diffrn_orient_matrix_UB_23      -0.0271731000
_diffrn_orient_matrix_UB_31      0.0175455000
_diffrn_orient_matrix_UB_32      0.0462859000
_diffrn_orient_matrix_UB_33      -0.0188601000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3773
_reflns_number_total             5319
_reflns_odcompleteness_completeness 96.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.866
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0467P)²+6.2349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1234
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Br19 Br 0.24177(2) 0.02467(5) 0.34590(3) 0.04808(17) Uani 1 1 d . . .
Br1 Br 0.25303(3) 0.27124(6) 0.64234(4) 0.05805(19) Uani 1 1 d . . .
P1 P 0.11424(6) -0.05966(11) 0.18753(7) 0.0308(3) Uani 1 1 d . . .
P1A P 0.38196(6) 0.18623(11) 0.79956(8) 0.0346(3) Uani 1 1 d . . .
O20 O 0.11623(16) 0.0649(3) 0.1398(2) 0.0430(8) Uani 1 1 d . . .
C3A C 0.3744(3) 0.1601(5) 0.6217(3) 0.0432(12) Uani 1 1 d . . .
H3A H 0.3486 0.1723 0.5618 0.052 Uiso 1 1 calc R . .
C10 C 0.0063(2) -0.1592(4) 0.2466(3) 0.0326(10) Uani 1 1 d . . .
C10A C 0.4888(2) 0.0907(4) 0.7375(3) 0.0378(11) Uani 1 1 d . . .
C9 C 0.0297(2) -0.1221(4) 0.1756(3) 0.0306(9) Uani 1 1 d . . .
C3 C 0.1207(2) -0.0900(4) 0.3643(3) 0.0372(11) Uani 1 1 d . . .
H3 H 0.1455 -0.0783 0.4246 0.045 Uiso 1 1 calc R . .
C9A C 0.4664(2) 0.1241(4) 0.8095(3) 0.0338(10) Uani 1 1 d . . .
C2A C 0.3440(2) 0.1974(4) 0.6809(3) 0.0377(11) Uani 1 1 d . . .
C2 C 0.1513(2) -0.0500(4) 0.3068(3) 0.0322(10) Uani 1 1 d . . .
C5A C 0.5560(3) 0.0426(5) 0.7571(4) 0.0532(14) Uani 1 1 d . . .
H5A H 0.5726 0.0184 0.7106 0.064 Uiso 1 1 calc R . .
C4 C 0.0501(2) -0.1526(5) 0.3450(3) 0.0398(11) Uani 1 1 d . . .
C4A C 0.4452(3) 0.1005(5) 0.6385(3) 0.0435(12) Uani 1 1 d . . .
C5 C -0.0609(2) -0.2081(5) 0.2253(3) 0.0490(13) Uani 1 1 d . . .
H5 H -0.0774 -0.2346 0.2713 0.059 Uiso 1 1 calc R . .
C6A C 0.5984(3) 0.0307(6) 0.8451(4) 0.0623(16) Uani 1 1 d . . .
H6A H 0.6435 0.0006 0.8578 0.075 Uiso 1 1 calc R . .
C11A C 0.3375(2) 0.0527(5) 0.8336(3) 0.0379(11) Uani 1 1 d . . .
C6 C -0.1035(3) -0.2181(5) 0.1378(4) 0.0546(14) Uani 1 1 d . . .
H6 H -0.1480 -0.2513 0.1254 0.065 Uiso 1 1 calc R . .
C12 C 0.1445(3) -0.3221(5) 0.1623(3) 0.0441(12) Uani 1 1 d . . .
H12 H 0.1089 -0.3434 0.1849 0.053 Uiso 1 1 calc R . .
C11 C 0.1603(2) -0.1917(4) 0.1540(3) 0.0341(10) Uani 1 1 d . . .
C7 C -0.0795(3) -0.1782(5) 0.0675(3) 0.0529(14) Uani 1 1 d . . .
H7 H -0.1082 -0.1830 0.0084 0.063 Uiso 1 1 calc R . .
C18 C 0.0627(3) -0.2949(5) 0.3824(4) 0.0576(15) Uani 1 1 d . . .
H18D H 0.0193 -0.3348 0.3791 0.086 Uiso 1 1 calc R . .
H18E H 0.0918 -0.2924 0.4437 0.086 Uiso 1 1 calc R . .
H18F H 0.0847 -0.3455 0.3475 0.086 Uiso 1 1 calc R . .
C15A C 0.3143(3) -0.1780(5) 0.8447(3) 0.0527(14) Uani 1 1 d . . .
H15A H 0.3235 -0.2657 0.8354 0.063 Uiso 1 1 calc R . .
C16A C 0.3508(3) -0.0775(5) 0.8193(3) 0.0441(12) Uani 1 1 d . . .
H16A H 0.3843 -0.0980 0.7927 0.053 Uiso 1 1 calc R . .
C16 C 0.2138(3) -0.1614(5) 0.1204(3) 0.0458(12) Uani 1 1 d . . .
H16 H 0.2251 -0.0739 0.1143 0.055 Uiso 1 1 calc R . .
C13 C 0.1810(3) -0.4219(5) 0.1374(4) 0.0525(13) Uani 1 1 d . . .
H13 H 0.1698 -0.5096 0.1431 0.063 Uiso 1 1 calc R . .
O20A O 0.38003(17) 0.3089(3) 0.8494(2) 0.0470(8) Uani 1 1 d . . .
C13A C 0.2513(3) -0.0193(6) 0.8977(4) 0.0677(17) Uani 1 1 d . . .
H13A H 0.2172 0.0001 0.9235 0.081 Uiso 1 1 calc R . .
C8A C 0.5129(3) 0.1097(5) 0.8998(4) 0.0528(14) Uani 1 1 d . . .
H8A H 0.4966 0.1359 0.9462 0.063 Uiso 1 1 calc R . .
C8 C -0.0148(2) -0.1329(5) 0.0862(3) 0.0419(11) Uani 1 1 d . . .
H8 H 0.0012 -0.1080 0.0394 0.050 Uiso 1 1 calc R . .
C15 C 0.2502(3) -0.2613(6) 0.0962(3) 0.0529(14) Uani 1 1 d . . .
H15 H 0.2862 -0.2406 0.0741 0.064 Uiso 1 1 calc R . .
C14A C 0.2650(3) -0.1469(6) 0.8831(4) 0.0584(15) Uani 1 1 d . . .
H14A H 0.2405 -0.2140 0.8996 0.070 Uiso 1 1 calc R . .
C18A C 0.4343(3) -0.0398(6) 0.5977(4) 0.0678(17) Uani 1 1 d . . .
H18A H 0.4146 -0.0953 0.6327 0.102 Uiso 1 1 calc R . .
H18B H 0.4778 -0.0755 0.5978 0.102 Uiso 1 1 calc R . .
H18C H 0.4036 -0.0357 0.5372 0.102 Uiso 1 1 calc R . .
C17A C 0.4824(3) 0.1859(7) 0.5872(4) 0.0727(18) Uani 1 1 d . . .
H17A H 0.4545 0.1922 0.5254 0.109 Uiso 1 1 calc R . .
H17B H 0.5260 0.1463 0.5909 0.109 Uiso 1 1 calc R . .
H17C H 0.4901 0.2724 0.6131 0.109 Uiso 1 1 calc R . .
C14 C 0.2338(3) -0.3906(6) 0.1044(3) 0.0532(14) Uani 1 1 d . . .
H14 H 0.2584 -0.4573 0.0875 0.064 Uiso 1 1 calc R . .
C12A C 0.2877(3) 0.0818(6) 0.8743(4) 0.0569(14) Uani 1 1 d . . .
H12A H 0.2790 0.1688 0.8858 0.068 Uiso 1 1 calc R . .
C7A C 0.5701(3) 0.0675(5) 0.9203(4) 0.0601(18) Uani 1 1 d . . .
H7A H 0.5964 0.0573 0.9801 0.072 Uiso 1 1 calc R . .
C17 C 0.0119(3) -0.0730(7) 0.3987(4) 0.0709(18) Uani 1 1 d . . .
H17D H 0.0017 0.0136 0.3734 0.106 Uiso 1 1 calc R . .
H17E H 0.0407 -0.0661 0.4601 0.106 Uiso 1 1 calc R . .
H17F H -0.0303 -0.1170 0.3961 0.106 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
Br19 C2 1.910(4) . ?
Br1 C2A 1.915(4) . ?
P1 O20 1.477(3) . ?
P1 C9 1.792(4) . ?
P1 C2 1.789(4) . ?
P1 C11 1.809(4) . ?
P1A C9A 1.795(4) . ?
P1A C2A 1.783(5) . ?
P1A C11A 1.804(5) . ?
P1A O20A 1.477(3) . ?
C3A H3A 0.9300 . ?
C3A C2A 1.324(6) . ?
C3A C4A 1.512(7) . ?
C10 C9 1.396(6) . ?
C10 C4 1.524(6) . ?
C10 C5 1.396(6) . ?
C10A C9A 1.391(6) . ?
C10A C5A 1.397(6) . ?
C10A C4A 1.532(7) . ?
C9 C8 1.417(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.315(6) . ?
C3 C4 1.515(6) . ?
C9A C8A 1.445(7) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.386(8) . ?
C4 C18 1.549(7) . ?
C4 C17 1.546(7) . ?
C4A C18A 1.548(7) . ?
C4A C17A 1.537(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(7) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.518(8) . ?
C11A C16A 1.381(7) . ?
C11A C12A 1.393(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.402(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(6) . ?
C12 C13 1.383(7) . ?
C11 C16 1.388(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.340(7) . ?
C18 H18D 0.9600 . ?
C18 H18E 0.9600 . ?
C18 H18F 0.9600 . ?
C15A H15A 0.9300 . ?
C15A C16A 1.394(7) . ?
C15A C14A 1.364(8) . ?
C16A H16A 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.379(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(7) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.360(8) . ?
C13A C12A 1.382(7) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.188(7) . ?
C8 H8 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.371(7) . ?
C14A H14A 0.9300 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C14 H14 0.9300 . ?
C12A H12A 0.9300 . ?
C7A H7A 0.9300 . ?
C17 H17D 0.9600 . ?
C17 H17E 0.9600 . ?
C17 H17F 0.9600 . ?

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
O20 P1 C9 115.45(19) . . ?
O20 P1 C2 114.53(19) . . ?
O20 P1 C11 112.70(19) . . ?
C9 P1 C11 106.2(2) . . ?
C2 P1 C9 101.7(2) . . ?
C2 P1 C11 105.05(19) . . ?
C9A P1A C11A 105.7(2) . . ?
C2A P1A C9A 101.6(2) . . ?
C2A P1A C11A 105.4(2) . . ?
O20A P1A C9A 115.8(2) . . ?
O20A P1A C2A 115.2(2) . . ?
O20A P1A C11A 112.0(2) . . ?
C2A C3A H3A 115.6 . . ?
C2A C3A C4A 128.7(4) . . ?
C4A C3A H3A 115.6 . . ?
C9 C10 C4 124.0(4) . . ?
C5 C10 C9 117.5(4) . . ?
C5 C10 C4 118.4(4) . . ?
C9A C10A C5A 117.3(5) . . ?
C9A C10A C4A 125.2(4) . . ?
C5A C10A C4A 117.5(4) . . ?
C10 C9 P1 125.0(3) . . ?
C10 C9 C8 119.9(4) . . ?
C8 C9 P1 115.2(3) . . ?
C2 C3 H3 115.9 . . ?
C2 C3 C4 128.2(4) . . ?
C4 C3 H3 115.9 . . ?
C10A C9A P1A 124.6(4) . . ?
C10A C9A C8A 119.5(4) . . ?
C8A C9A P1A 115.9(3) . . ?
P1A C2A Br1 114.4(2) . . ?
C3A C2A Br1 120.7(4) . . ?
C3A C2A P1A 124.9(4) . . ?
P1 C2 Br19 113.8(2) . . ?
C3 C2 Br19 121.5(3) . . ?
C3 C2 P1 124.7(3) . . ?
C10A C5A H5A 119.6 . . ?
C6A C5A C10A 120.8(5) . . ?
C6A C5A H5A 119.6 . . ?
C10 C4 C18 108.6(4) . . ?
C10 C4 C17 110.0(4) . . ?
C3 C4 C10 116.0(4) . . ?
C3 C4 C18 106.3(4) . . ?
C3 C4 C17 106.4(4) . . ?
C17 C4 C18 109.4(4) . . ?
C3A C4A C10A 114.8(4) . . ?
C3A C4A C18A 106.9(4) . . ?
C3A C4A C17A 106.7(4) . . ?
C10A C4A C18A 108.8(4) . . ?
C10A C4A C17A 110.2(4) . . ?
C17A C4A C18A 109.4(4) . . ?
C10 C5 H5 119.1 . . ?
C6 C5 C10 121.8(5) . . ?
C6 C5 H5 119.1 . . ?
C5A C6A H6A 120.5 . . ?
C5A C6A C7A 119.0(5) . . ?
C7A C6A H6A 120.5 . . ?
C16A C11A P1A 121.7(4) . . ?
C16A C11A C12A 119.2(4) . . ?
C12A C11A P1A 119.1(4) . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(5) . . ?
C7 C6 H6 120.1 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.9(5) . . ?
C13 C12 H12 119.6 . . ?
C12 C11 P1 121.7(3) . . ?
C12 C11 C16 119.0(4) . . ?
C16 C11 P1 119.3(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(5) . . ?
C8 C7 H7 120.3 . . ?
C4 C18 H18D 109.5 . . ?
C4 C18 H18E 109.5 . . ?
C4 C18 H18F 109.5 . . ?
H18D C18 H18E 109.5 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C16A C15A H15A 120.2 . . ?
C14A C15A H15A 120.2 . . ?
C14A C15A C16A 119.6(5) . . ?
C11A C16A C15A 120.1(5) . . ?
C11A C16A H16A 119.9 . . ?
C15A C16A H16A 119.9 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 119.9(5) . . ?
C15 C16 H16 120.0 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C14A C13A H13A 119.8 . . ?
C14A C13A C12A 120.3(5) . . ?
C12A C13A H13A 119.8 . . ?
C9A C8A H8A 117.0 . . ?
C7A C8A C9A 126.0(5) . . ?
C7A C8A H8A 117.0 . . ?
C9 C8 H8 119.2 . . ?
C7 C8 C9 121.5(4) . . ?
C7 C8 H8 119.2 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.5(5) . . ?
C14 C15 H15 119.7 . . ?
C15A C14A H14A 119.5 . . ?
C13A C14A C15A 121.0(5) . . ?
C13A C14A H14A 119.5 . . ?
C4A C18A H18A 109.5 . . ?
C4A C18A H18B 109.5 . . ?
C4A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C4A C17A H17A 109.5 . . ?
C4A C17A H17B 109.5 . . ?
C4A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(5) . . ?
C15 C14 H14 120.0 . . ?
C11A C12A H12A 120.1 . . ?
C13A C12A C11A 119.8(5) . . ?
C13A C12A H12A 120.1 . . ?
C6A C7A H7A 121.3 . . ?
C8A C7A C6A 117.5(5) . . ?
C8A C7A H7A 121.3 . . ?
C4 C17 H17D 109.5 . . ?
C4 C17 H17E 109.5 . . ?
C4 C17 H17F 109.5 . . ?
H17D C17 H17E 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C9 C8 C7 180.0(4) . . . . ?
P1 C11 C16 C15 178.8(4) . . . . ?
P1A C9A C8A C7A 178.1(5) . . . . ?
P1A C11A C16A C15A -178.5(4) . . . . ?
P1A C11A C12A C13A 177.5(4) . . . . ?
O20 P1 C9 C10 -128.5(4) . . . . ?
O20 P1 C9 C8 51.5(4) . . . . ?
O20 P1 C2 Br19 -51.1(3) . . . . ?
O20 P1 C2 C3 129.1(4) . . . . ?
O20 P1 C11 C12 -155.2(4) . . . . ?
O20 P1 C11 C16 26.1(4) . . . . ?
C10 C9 C8 C7 0.0(7) . . . . ?
C10 C5 C6 C7 -0.2(8) . . . . ?
C10A C9A C8A C7A -2.2(8) . . . . ?
C10A C5A C6A C7A 1.5(8) . . . . ?
C9 P1 C2 Br19 -176.3(2) . . . . ?
C9 P1 C2 C3 3.9(4) . . . . ?
C9 P1 C11 C12 -27.8(4) . . . . ?
C9 P1 C11 C16 153.4(4) . . . . ?
C9 C10 C4 C3 5.7(7) . . . . ?
C9 C10 C4 C18 -113.9(5) . . . . ?
C9 C10 C4 C17 126.5(5) . . . . ?
C9 C10 C5 C6 -0.9(7) . . . . ?
C9A P1A C2A Br1 -176.6(2) . . . . ?
C9A P1A C2A C3A 2.9(5) . . . . ?
C9A P1A C11A C16A -31.7(4) . . . . ?
C9A P1A C11A C12A 149.2(4) . . . . ?
C9A C10A C5A C6A -0.7(7) . . . . ?
C9A C10A C4A C3A 4.2(7) . . . . ?
C9A C10A C4A C18A -115.5(5) . . . . ?
C9A C10A C4A C17A 124.5(5) . . . . ?
C9A C8A C7A C6A 2.9(8) . . . . ?
C2A P1A C9A C10A -2.8(4) . . . . ?
C2A P1A C9A C8A 176.9(3) . . . . ?
C2A P1A C11A C16A 75.4(4) . . . . ?
C2A P1A C11A C12A -103.7(4) . . . . ?
C2A C3A C4A C10A -4.3(7) . . . . ?
C2A C3A C4A C18A 116.5(6) . . . . ?
C2A C3A C4A C17A -126.6(6) . . . . ?
C2 P1 C9 C10 -3.9(4) . . . . ?
C2 P1 C9 C8 176.1(3) . . . . ?
C2 P1 C11 C12 79.5(4) . . . . ?
C2 P1 C11 C16 -99.3(4) . . . . ?
C2 C3 C4 C10 -6.0(7) . . . . ?
C2 C3 C4 C18 114.8(5) . . . . ?
C2 C3 C4 C17 -128.7(5) . . . . ?
C5A C10A C9A P1A -179.5(4) . . . . ?
C5A C10A C9A C8A 0.8(7) . . . . ?
C5A C10A C4A C3A -176.9(4) . . . . ?
C5A C10A C4A C18A 63.5(6) . . . . ?
C5A C10A C4A C17A -56.5(6) . . . . ?
C5A C6A C7A C8A -2.6(8) . . . . ?
C4 C10 C9 P1 -0.5(6) . . . . ?
C4 C10 C9 C8 179.5(4) . . . . ?
C4 C10 C5 C6 -179.4(5) . . . . ?
C4 C3 C2 Br19 -179.1(4) . . . . ?
C4 C3 C2 P1 0.7(7) . . . . ?
C4A C3A C2A Br1 179.9(4) . . . . ?
C4A C3A C2A P1A 0.5(8) . . . . ?
C4A C10A C9A P1A -0.5(7) . . . . ?
C4A C10A C9A C8A 179.8(4) . . . . ?
C4A C10A C5A C6A -179.8(5) . . . . ?
C5 C10 C9 P1 -179.0(4) . . . . ?
C5 C10 C9 C8 1.0(7) . . . . ?
C5 C10 C4 C3 -175.9(4) . . . . ?
C5 C10 C4 C18 64.5(5) . . . . ?
C5 C10 C4 C17 -55.1(6) . . . . ?
C5 C6 C7 C8 1.2(8) . . . . ?
C11A P1A C9A C10A 107.0(4) . . . . ?
C11A P1A C9A C8A -73.3(4) . . . . ?
C11A P1A C2A Br1 73.4(3) . . . . ?
C11A P1A C2A C3A -107.2(4) . . . . ?
C6 C7 C8 C9 -1.1(8) . . . . ?
C12 C11 C16 C15 0.0(7) . . . . ?
C12 C13 C14 C15 0.1(8) . . . . ?
C11 P1 C9 C10 105.8(4) . . . . ?
C11 P1 C9 C8 -74.2(4) . . . . ?
C11 P1 C2 Br19 73.1(3) . . . . ?
C11 P1 C2 C3 -106.7(4) . . . . ?
C11 C12 C13 C14 0.3(8) . . . . ?
C11 C16 C15 C14 0.4(8) . . . . ?
C16A C11A C12A C13A -1.6(8) . . . . ?
C16A C15A C14A C13A -0.5(8) . . . . ?
C16 C15 C14 C13 -0.4(8) . . . . ?
C13 C12 C11 P1 -179.1(4) . . . . ?
C13 C12 C11 C16 -0.3(7) . . . . ?
O20A P1A C9A C10A -128.4(4) . . . . ?
O20A P1A C9A C8A 51.3(4) . . . . ?
O20A P1A C2A Br1 -50.6(3) . . . . ?
O20A P1A C2A C3A 128.8(4) . . . . ?
O20A P1A C11A C16A -158.6(4) . . . . ?
O20A P1A C11A C12A 22.3(5) . . . . ?
C14A C15A C16A C11A 0.4(8) . . . . ?
C14A C13A C12A C11A 1.7(9) . . . . ?
C12A C11A C16A C15A 0.6(7) . . . . ?
C12A C13A C14A C15A -0.6(9) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1026527'
#######################################################################
#
#                 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_abs652
_audit_creation_date             2014-04-15
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C34 H32 O2 P2'
_chemical_formula_sum            'C34 H32 O2 P2'
_chemical_formula_weight         534.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c34 h28 o1 p1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.56214(10)
_cell_length_b                   11.41592(10)
_cell_length_c                   21.7492(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.0890(9)
_cell_angle_gamma                90.00
_cell_volume                     2826.34(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.1400
_cell_measurement_theta_min      3.8770
_exptl_absorpt_coefficient_mu    1.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            43797
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         72.50
_diffrn_reflns_theta_min         3.88
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9497
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000 -180.0000 128

#__ type_ start__ end____ width___ exp.time_
  2 omega  -34.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   60.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega   83.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   60.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 66

#__ type_ start__ end____ width___ exp.time_
  6 omega   71.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega   84.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
  8 omega   47.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   66.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   61.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 12 omega  105.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega  135.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   60.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega  149.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega  122.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega  135.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
 18 omega   70.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   84.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   97.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega   80.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -17.0000   15.2033 31

#__ type_ start__ end____ width___ exp.time_
 22 omega   44.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 23 omega   79.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 24 omega   89.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
 25 omega  137.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   79.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 27 omega   65.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -35.0000   -5.8699 25

#__ type_ start__ end____ width___ exp.time_
 28 omega   60.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -38.0000 -117.0000 29

#__ type_ start__ end____ width___ exp.time_
 29 omega   67.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
 30 omega   48.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 31 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 32 omega   51.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 33 omega   79.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 34 omega  108.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 35 omega   49.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 36 omega  -40.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 37 omega  -87.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -19.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 38 omega -119.00  -22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000  150.0000 97

#__ type_ start__ end____ width___ exp.time_
 39 omega   87.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 40 omega   80.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   72.0000  148.3541 27

#__ type_ start__ end____ width___ exp.time_
 41 omega   68.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   17.0000 -175.8390 63

#__ type_ start__ end____ width___ exp.time_
 42 omega   81.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   69.0000   92.0647 26

#__ type_ start__ end____ width___ exp.time_
 43 omega   46.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 44 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   60.0000  137.2145 26

#__ type_ start__ end____ width___ exp.time_
 45 omega   60.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 46 omega   83.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 47 omega   86.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 48 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 49 omega   83.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 50 omega   36.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 51 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 52 omega   73.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 53 omega   80.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 54 omega   79.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 55 omega   85.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
 56 omega  153.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 57 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 58 omega   30.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -60.0000 75

#__ type_ start__ end____ width___ exp.time_
 59 omega  130.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 60 omega   85.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
 61 omega   38.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 62 omega  122.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 63 omega   56.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 64 omega   72.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 65 omega   86.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 66 omega   89.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 67 omega  125.00  151.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   69.0000   92.0647 26

#__ type_ start__ end____ width___ exp.time_
 68 omega   84.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 69 omega  112.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 70 omega  125.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   24.0000  144.1619 25

#__ type_ start__ end____ width___ exp.time_
 71 omega   71.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 72 omega   42.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 73 omega   90.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 74 omega   84.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 75 omega   84.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 76 omega   88.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 77 omega   89.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 78 omega   42.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 79 omega  120.00  151.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 80 omega   77.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   24.0000  144.1619 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0119385000
_diffrn_orient_matrix_UB_12      -0.0495606000
_diffrn_orient_matrix_UB_13      0.0667240000
_diffrn_orient_matrix_UB_21      0.1285728000
_diffrn_orient_matrix_UB_22      0.0419174000
_diffrn_orient_matrix_UB_23      0.0143203000
_diffrn_orient_matrix_UB_31      -0.0405599000
_diffrn_orient_matrix_UB_32      0.1182656000
_diffrn_orient_matrix_UB_33      0.0228505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5047
_reflns_number_total             5595
_reflns_odcompleteness_completeness 94.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0477P)²+1.5430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0929
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.00193(3) 0.29640(3) 0.107904(16) 0.01231(9) Uani 1 1 d . . .
P20 P 0.37863(3) 0.32275(3) 0.185353(17) 0.01589(10) Uani 1 1 d . . .
O13 O -0.05838(8) 0.41208(9) 0.10287(5) 0.0174(2) Uani 1 1 d . . .
O32 O 0.41335(10) 0.30490(10) 0.25402(5) 0.0242(2) Uani 1 1 d . . .
C33 C 0.39235(12) 0.18957(13) 0.14200(7) 0.0172(3) Uani 1 1 d . . .
C21 C 0.22974(12) 0.37254(13) 0.16131(6) 0.0148(3) Uani 1 1 d . . .
C2 C 0.13401(12) 0.28615(12) 0.16523(6) 0.0144(3) Uani 1 1 d . . .
C5 C -0.13759(13) 0.01836(13) 0.18903(7) 0.0188(3) Uani 1 1 d . . .
H5 H -0.1155 -0.0369 0.2203 0.023 Uiso 1 1 calc R . .
C4 C 0.06886(12) 0.09668(13) 0.21510(7) 0.0170(3) Uani 1 1 d . . .
C34 C 0.42663(12) 0.08626(14) 0.17445(8) 0.0210(3) Uani 1 1 d . . .
H34 H 0.4428 0.0866 0.2179 0.025 Uiso 1 1 calc R . .
C19 C 0.07444(12) 0.35104(13) -0.00189(7) 0.0157(3) Uani 1 1 d . . .
H19 H 0.0652 0.4279 0.0105 0.019 Uiso 1 1 calc R . .
C3 C 0.14968(12) 0.19581(13) 0.20497(6) 0.0163(3) Uani 1 1 d . . .
H3 H 0.2229 0.1938 0.2307 0.020 Uiso 1 1 calc R . .
C36 C 0.41240(13) -0.01721(14) 0.07724(9) 0.0259(3) Uani 1 1 d . . .
H36 H 0.4188 -0.0864 0.0556 0.031 Uiso 1 1 calc R . .
C28 C 0.46337(12) 0.43050(13) 0.15285(7) 0.0191(3) Uani 1 1 d . . .
C9 C -0.08957(12) 0.18056(12) 0.12812(7) 0.0147(3) Uani 1 1 d . . .
C16 C 0.10330(13) 0.12163(13) -0.03882(7) 0.0191(3) Uani 1 1 d . . .
H16 H 0.1134 0.0449 -0.0512 0.023 Uiso 1 1 calc R . .
C10 C -0.05396(12) 0.09977(13) 0.17580(7) 0.0159(3) Uani 1 1 d . . .
C15 C 0.06443(12) 0.14365(13) 0.01716(7) 0.0173(3) Uani 1 1 d . . .
H15 H 0.0487 0.0817 0.0422 0.021 Uiso 1 1 calc R . .
C35 C 0.43674(13) -0.01710(14) 0.14202(8) 0.0251(3) Uani 1 1 d . . .
H35 H 0.4597 -0.0859 0.1637 0.030 Uiso 1 1 calc R . .
C8 C -0.20577(13) 0.18078(13) 0.09528(7) 0.0181(3) Uani 1 1 d . . .
H8 H -0.2284 0.2354 0.0638 0.022 Uiso 1 1 calc R . .
C14 C 0.04914(11) 0.25866(12) 0.03559(6) 0.0138(3) Uani 1 1 d . . .
C18 C 0.11337(13) 0.32874(13) -0.05762(7) 0.0180(3) Uani 1 1 d . . .
H18 H 0.1302 0.3905 -0.0825 0.022 Uiso 1 1 calc R . .
C17 C 0.12706(13) 0.21383(14) -0.07618(7) 0.0189(3) Uani 1 1 d . . .
H17 H 0.1522 0.1988 -0.1137 0.023 Uiso 1 1 calc R . .
C7 C -0.28674(13) 0.10026(13) 0.10953(7) 0.0203(3) Uani 1 1 d . . .
H7 H -0.3636 0.1008 0.0878 0.024 Uiso 1 1 calc R . .
C37 C 0.37844(13) 0.08544(14) 0.04445(8) 0.0244(3) Uani 1 1 d . . .
H37 H 0.3626 0.0848 0.0010 0.029 Uiso 1 1 calc R . .
C38 C 0.36836(13) 0.18876(14) 0.07674(7) 0.0204(3) Uani 1 1 d . . .
H38 H 0.3456 0.2575 0.0550 0.025 Uiso 1 1 calc R . .
C6 C -0.25200(13) 0.01848(13) 0.15667(7) 0.0205(3) Uani 1 1 d . . .
H6 H -0.3057 -0.0361 0.1664 0.025 Uiso 1 1 calc R . .
C11 C 0.13063(14) -0.01867(14) 0.20242(8) 0.0263(3) Uani 1 1 d . . .
H11A H 0.1380 -0.0222 0.1592 0.039 Uiso 1 1 calc R . .
H11B H 0.0850 -0.0841 0.2123 0.039 Uiso 1 1 calc R . .
H11C H 0.2073 -0.0214 0.2279 0.039 Uiso 1 1 calc R . .
C12 C 0.05940(14) 0.10295(16) 0.28494(7) 0.0254(3) Uani 1 1 d . . .
H12A H 0.1366 0.1091 0.3096 0.038 Uiso 1 1 calc R . .
H12B H 0.0218 0.0334 0.2965 0.038 Uiso 1 1 calc R . .
H12C H 0.0139 0.1703 0.2922 0.038 Uiso 1 1 calc R . .
C29 C 0.42030(13) 0.54146(14) 0.13437(7) 0.0209(3) Uani 1 1 d . . .
C22 C 0.20913(12) 0.48332(13) 0.14268(7) 0.0168(3) Uani 1 1 d . . .
H22 H 0.1302 0.5035 0.1322 0.020 Uiso 1 1 calc R . .
C23 C 0.29445(12) 0.58096(13) 0.13599(7) 0.0189(3) Uani 1 1 d . . .
C31 C 0.29626(14) 0.66414(14) 0.19234(9) 0.0275(4) Uani 1 1 d . . .
H31A H 0.3254 0.6227 0.2303 0.041 Uiso 1 1 calc R . .
H31B H 0.2181 0.6915 0.1932 0.041 Uiso 1 1 calc R . .
H31C H 0.3464 0.7297 0.1884 0.041 Uiso 1 1 calc R . .
C30 C 0.24308(15) 0.64702(17) 0.07557(9) 0.0350(4) Uani 1 1 d . . .
H30A H 0.2876 0.7171 0.0727 0.053 Uiso 1 1 calc R . .
H30B H 0.1627 0.6672 0.0763 0.053 Uiso 1 1 calc R . .
H30C H 0.2469 0.5979 0.0401 0.053 Uiso 1 1 calc R . .
C27 C 0.57969(13) 0.39901(15) 0.14940(8) 0.0253(3) Uani 1 1 d . . .
H27 H 0.6068 0.3246 0.1620 0.030 Uiso 1 1 calc R . .
C24 C 0.49848(15) 0.62070(16) 0.11482(10) 0.0330(4) Uani 1 1 d . . .
H24 H 0.4731 0.6964 0.1039 0.040 Uiso 1 1 calc R . .
C26 C 0.65386(14) 0.47720(16) 0.12762(10) 0.0340(4) Uani 1 1 d . . .
H26 H 0.7298 0.4554 0.1239 0.041 Uiso 1 1 calc R . .
C25 C 0.61281(16) 0.58941(17) 0.11126(12) 0.0406(5) Uani 1 1 d . . .
H25 H 0.6626 0.6440 0.0978 0.049 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 O13 1.4884(10) . ?
P1 C2 1.7982(14) . ?
P1 C9 1.7957(14) . ?
P1 C14 1.8049(14) . ?
P20 O32 1.4909(11) . ?
P20 C33 1.8106(15) . ?
P20 C21 1.8013(14) . ?
P20 C28 1.7931(15) . ?
C33 C34 1.396(2) . ?
C33 C38 1.398(2) . ?
C21 C2 1.4960(18) . ?
C21 C22 1.337(2) . ?
C2 C3 1.337(2) . ?
C5 H5 0.9300 . ?
C5 C10 1.407(2) . ?
C5 C6 1.385(2) . ?
C4 C3 1.5082(19) . ?
C4 C10 1.5242(19) . ?
C4 C11 1.546(2) . ?
C4 C12 1.5436(19) . ?
C34 H34 0.9300 . ?
C34 C35 1.390(2) . ?
C19 H19 0.9300 . ?
C19 C14 1.395(2) . ?
C19 C18 1.388(2) . ?
C3 H3 0.9300 . ?
C36 H36 0.9300 . ?
C36 C35 1.388(3) . ?
C36 C37 1.392(2) . ?
C28 C29 1.394(2) . ?
C28 C27 1.407(2) . ?
C9 C10 1.395(2) . ?
C9 C8 1.407(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.392(2) . ?
C16 C17 1.386(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.393(2) . ?
C35 H35 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.385(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.390(2) . ?
C17 H17 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.393(2) . ?
C37 H37 0.9300 . ?
C37 C38 1.388(2) . ?
C38 H38 0.9300 . ?
C6 H6 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C29 C23 1.530(2) . ?
C29 C24 1.397(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.5123(19) . ?
C23 C31 1.548(2) . ?
C23 C30 1.541(2) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C27 H27 0.9300 . ?
C27 C26 1.378(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(2) . ?
C26 H26 0.9300 . ?
C26 C25 1.391(3) . ?
C25 H25 0.9300 . ?

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
O13 P1 C2 116.03(6) . . ?
O13 P1 C9 112.51(6) . . ?
O13 P1 C14 110.92(6) . . ?
C2 P1 C14 103.82(6) . . ?
C9 P1 C2 104.33(7) . . ?
C9 P1 C14 108.58(6) . . ?
O32 P20 C33 111.97(7) . . ?
O32 P20 C21 114.19(6) . . ?
O32 P20 C28 114.76(7) . . ?
C21 P20 C33 106.27(6) . . ?
C28 P20 C33 105.48(7) . . ?
C28 P20 C21 103.27(7) . . ?
C34 C33 P20 119.30(12) . . ?
C34 C33 C38 119.74(14) . . ?
C38 C33 P20 120.96(11) . . ?
C2 C21 P20 117.03(10) . . ?
C22 C21 P20 119.81(11) . . ?
C22 C21 C2 123.14(13) . . ?
C21 C2 P1 117.68(10) . . ?
C3 C2 P1 120.05(11) . . ?
C3 C2 C21 121.83(13) . . ?
C10 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C6 C5 C10 121.65(14) . . ?
C3 C4 C10 116.17(12) . . ?
C3 C4 C11 107.20(12) . . ?
C3 C4 C12 105.16(12) . . ?
C10 C4 C11 109.50(12) . . ?
C10 C4 C12 109.34(12) . . ?
C12 C4 C11 109.24(13) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.16(15) . . ?
C35 C34 H34 119.9 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C14 120.32(13) . . ?
C2 C3 C4 130.98(13) . . ?
C2 C3 H3 114.5 . . ?
C4 C3 H3 114.5 . . ?
C35 C36 H36 119.7 . . ?
C35 C36 C37 120.54(15) . . ?
C37 C36 H36 119.7 . . ?
C29 C28 P20 123.00(11) . . ?
C29 C28 C27 120.88(14) . . ?
C27 C28 P20 116.06(12) . . ?
C10 C9 P1 123.99(11) . . ?
C10 C9 C8 120.66(13) . . ?
C8 C9 P1 115.19(11) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C17 C16 C15 120.18(13) . . ?
C5 C10 C4 118.44(13) . . ?
C9 C10 C5 117.70(13) . . ?
C9 C10 C4 123.84(13) . . ?
C16 C15 H15 120.0 . . ?
C16 C15 C14 119.90(13) . . ?
C14 C15 H15 120.0 . . ?
C34 C35 H35 120.1 . . ?
C36 C35 C34 119.73(15) . . ?
C36 C35 H35 120.1 . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.53(14) . . ?
C7 C8 H8 119.7 . . ?
C19 C14 P1 117.07(11) . . ?
C15 C14 P1 123.29(11) . . ?
C15 C14 C19 119.61(13) . . ?
C19 C18 H18 120.1 . . ?
C19 C18 C17 119.83(13) . . ?
C17 C18 H18 120.1 . . ?
C16 C17 C18 120.15(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C8 C7 H7 120.3 . . ?
C8 C7 C6 119.36(14) . . ?
C6 C7 H7 120.3 . . ?
C36 C37 H37 120.1 . . ?
C38 C37 C36 119.82(15) . . ?
C38 C37 H37 120.1 . . ?
C33 C38 H38 120.0 . . ?
C37 C38 C33 120.00(14) . . ?
C37 C38 H38 120.0 . . ?
C5 C6 C7 120.09(13) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C28 C29 C23 123.67(13) . . ?
C28 C29 C24 117.30(14) . . ?
C24 C29 C23 119.02(14) . . ?
C21 C22 H22 115.0 . . ?
C21 C22 C23 129.93(13) . . ?
C23 C22 H22 115.0 . . ?
C29 C23 C31 108.55(12) . . ?
C29 C23 C30 110.54(13) . . ?
C22 C23 C29 115.10(12) . . ?
C22 C23 C31 107.13(12) . . ?
C22 C23 C30 106.39(12) . . ?
C30 C23 C31 108.95(14) . . ?
C23 C31 H31A 109.5 . . ?
C23 C31 H31B 109.5 . . ?
C23 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C23 C30 H30A 109.5 . . ?
C23 C30 H30B 109.5 . . ?
C23 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C27 H27 119.6 . . ?
C26 C27 C28 120.75(16) . . ?
C26 C27 H27 119.6 . . ?
C29 C24 H24 119.2 . . ?
C25 C24 C29 121.68(17) . . ?
C25 C24 H24 119.2 . . ?
C27 C26 H26 120.7 . . ?
C27 C26 C25 118.65(15) . . ?
C25 C26 H26 120.7 . . ?
C24 C25 C26 120.65(16) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?

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
P1 C2 C3 C4 -5.0(2) . . . . ?
P1 C9 C10 C5 175.99(10) . . . . ?
P1 C9 C10 C4 -2.5(2) . . . . ?
P1 C9 C8 C7 -175.93(11) . . . . ?
P20 C33 C34 C35 179.48(11) . . . . ?
P20 C33 C38 C37 -179.43(11) . . . . ?
P20 C21 C2 P1 -147.21(8) . . . . ?
P20 C21 C2 C3 25.17(17) . . . . ?
P20 C21 C22 C23 2.0(2) . . . . ?
P20 C28 C29 C23 -3.9(2) . . . . ?
P20 C28 C29 C24 174.59(13) . . . . ?
P20 C28 C27 C26 -177.28(14) . . . . ?
O13 P1 C2 C21 -55.46(12) . . . . ?
O13 P1 C2 C3 132.02(11) . . . . ?
O13 P1 C9 C10 -130.82(12) . . . . ?
O13 P1 C9 C8 44.59(12) . . . . ?
O13 P1 C14 C19 28.25(12) . . . . ?
O13 P1 C14 C15 -153.79(11) . . . . ?
O32 P20 C33 C34 2.91(13) . . . . ?
O32 P20 C33 C38 -177.53(11) . . . . ?
O32 P20 C21 C2 -71.23(12) . . . . ?
O32 P20 C21 C22 107.02(12) . . . . ?
O32 P20 C28 C29 -105.59(14) . . . . ?
O32 P20 C28 C27 71.59(14) . . . . ?
C33 P20 C21 C2 52.71(12) . . . . ?
C33 P20 C21 C22 -129.04(12) . . . . ?
C33 P20 C28 C29 130.69(13) . . . . ?
C33 P20 C28 C27 -52.14(14) . . . . ?
C33 C34 C35 C36 -0.1(2) . . . . ?
C21 P20 C33 C34 -122.40(11) . . . . ?
C21 P20 C33 C38 57.16(13) . . . . ?
C21 P20 C28 C29 19.34(15) . . . . ?
C21 P20 C28 C27 -163.49(12) . . . . ?
C21 C2 C3 C4 -177.24(13) . . . . ?
C21 C22 C23 C29 17.0(2) . . . . ?
C21 C22 C23 C31 -103.77(18) . . . . ?
C21 C22 C23 C30 139.81(17) . . . . ?
C2 P1 C9 C10 -4.23(13) . . . . ?
C2 P1 C9 C8 171.18(11) . . . . ?
C2 P1 C14 C19 -97.05(11) . . . . ?
C2 P1 C14 C15 80.92(13) . . . . ?
C2 C21 C22 C23 -179.91(14) . . . . ?
C34 C33 C38 C37 0.1(2) . . . . ?
C19 C18 C17 C16 -0.8(2) . . . . ?
C3 C4 C10 C5 -171.87(12) . . . . ?
C3 C4 C10 C9 6.6(2) . . . . ?
C36 C37 C38 C33 0.0(2) . . . . ?
C28 P20 C33 C34 128.39(12) . . . . ?
C28 P20 C33 C38 -52.05(13) . . . . ?
C28 P20 C21 C2 163.47(10) . . . . ?
C28 P20 C21 C22 -18.27(13) . . . . ?
C28 C29 C23 C22 -15.5(2) . . . . ?
C28 C29 C23 C31 104.55(17) . . . . ?
C28 C29 C23 C30 -136.01(16) . . . . ?
C28 C29 C24 C25 2.7(3) . . . . ?
C28 C27 C26 C25 2.3(3) . . . . ?
C9 P1 C2 C21 -179.83(10) . . . . ?
C9 P1 C2 C3 7.65(13) . . . . ?
C9 P1 C14 C19 152.37(11) . . . . ?
C9 P1 C14 C15 -29.67(14) . . . . ?
C9 C8 C7 C6 -0.2(2) . . . . ?
C16 C15 C14 P1 -178.76(11) . . . . ?
C16 C15 C14 C19 -0.8(2) . . . . ?
C10 C5 C6 C7 0.2(2) . . . . ?
C10 C4 C3 C2 -2.6(2) . . . . ?
C10 C9 C8 C7 -0.3(2) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C35 C36 C37 C38 -0.2(2) . . . . ?
C8 C9 C10 C5 0.8(2) . . . . ?
C8 C9 C10 C4 -177.68(13) . . . . ?
C8 C7 C6 C5 0.3(2) . . . . ?
C14 P1 C2 C21 66.50(12) . . . . ?
C14 P1 C2 C3 -106.02(12) . . . . ?
C14 P1 C9 C10 106.01(12) . . . . ?
C14 P1 C9 C8 -78.57(12) . . . . ?
C14 C19 C18 C17 0.1(2) . . . . ?
C18 C19 C14 P1 178.78(11) . . . . ?
C18 C19 C14 C15 0.7(2) . . . . ?
C17 C16 C15 C14 0.1(2) . . . . ?
C37 C36 C35 C34 0.3(2) . . . . ?
C38 C33 C34 C35 -0.1(2) . . . . ?
C6 C5 C10 C4 177.81(13) . . . . ?
C6 C5 C10 C9 -0.8(2) . . . . ?
C11 C4 C3 C2 120.16(17) . . . . ?
C11 C4 C10 C5 66.56(16) . . . . ?
C11 C4 C10 C9 -114.95(15) . . . . ?
C12 C4 C3 C2 -123.65(16) . . . . ?
C12 C4 C10 C5 -53.10(17) . . . . ?
C12 C4 C10 C9 125.39(14) . . . . ?
C29 C28 C27 C26 0.0(3) . . . . ?
C29 C24 C25 C26 -0.4(3) . . . . ?
C22 C21 C2 P1 34.60(18) . . . . ?
C22 C21 C2 C3 -153.02(14) . . . . ?
C23 C29 C24 C25 -178.78(19) . . . . ?
C27 C28 C29 C23 179.10(15) . . . . ?
C27 C28 C29 C24 -2.5(2) . . . . ?
C27 C26 C25 C24 -2.1(3) . . . . ?
C24 C29 C23 C22 166.11(15) . . . . ?
C24 C29 C23 C31 -73.87(19) . . . . ?
C24 C29 C23 C30 45.6(2) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1026526'
#######################################################################
#
#                 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_asb_421
_audit_creation_date             2014-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C8.5 H9.5 O P0.5)'
_chemical_formula_sum            'C17 H19 O2 P'
_chemical_formula_weight         286.29
_chemical_melting_point          ?

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   35.515(2)
_cell_length_b                   14.5644(7)
_cell_length_c                   5.7956(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2997.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4505
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7370
_cell_measurement_theta_min      5.0450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16589
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.149
_diffrn_reflns_theta_min         3.925
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -126.00  -78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 83

#__ type_ start__ end____ width___ exp.time_
  4 omega   69.00   96.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00   63.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   99.00  139.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  128.0000  -52.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00   97.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega  102.00  130.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  9 omega  143.00  170.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   70.00  109.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
 11 omega  115.00  147.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega   37.00   69.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 13 omega   77.00  109.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 14 omega   97.00  166.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
 15 omega   77.00  146.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
 16 omega   68.00   93.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   30.00   63.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
 18 omega   58.00   83.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   46.00   71.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   37.00   71.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 21 omega -107.00  -63.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -144.0000   63.0000 44

#__ type_ start__ end____ width___ exp.time_
 22 omega   86.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 23 omega   21.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 24 omega  134.00  166.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 25 omega  134.00  161.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   32.00   63.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 27 omega  105.00  143.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
 28 omega   97.00  143.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  120.0000 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0403799000
_diffrn_orient_matrix_UB_12      -0.0386527000
_diffrn_orient_matrix_UB_13      -0.0033635000
_diffrn_orient_matrix_UB_21      0.0004372000
_diffrn_orient_matrix_UB_22      -0.0064771000
_diffrn_orient_matrix_UB_23      0.2654668000
_diffrn_orient_matrix_UB_31      -0.0158345000
_diffrn_orient_matrix_UB_32      0.0981881000
_diffrn_orient_matrix_UB_33      0.0161358000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2732
_reflns_number_total             3265
_reflns_odcompleteness_completeness 94.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0679
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²+4.4754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1799
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O13A-H14A
 1.8 with sigma of 0.02
 O13-H14
 1.8 with sigma of 0.02
 O14-H14
 0.9 with sigma of 0.02
 C5A-H5AB = C5A-H5AC = C5A-H5AA
 0.95 with sigma of 0.02
 C1A-H1AA = C1A-H1AB
 0.95 with sigma of 0.02
 C1A-H1AC
 0.95 with sigma of 0.02
 C1-H1B = C1-H1A = C1-H1C
 0.95 with sigma of 0.02
 H1B-C2
 2.1 with sigma of 0.02
 H1A-C2
 2.1 with sigma of 0.02
 H1C-C2
 2.1 with sigma of 0.02
 H1B-H1C
 1.6 with sigma of 0.02
 C5-H5B = C5-H5A
 0.95 with sigma of 0.02
 H5B-H5A
 1.6 with sigma of 0.02
 H5A-C2
 2.1 with sigma of 0.02
 H5B-C2
 2.1 with sigma of 0.02
 C5-H5C
 0.95 with sigma of 0.02
3. Others
 Fixed Sof: O14A(0.5) H14A(0.5) C1A(0.5) H1AB(0.5) H1AC(0.5) C5A(0.5)
 H5AA(0.5) H5AB(0.5) H5AC(0.5) H9A(0.5) H9AA(0.5) C7A(0.5) H7A(0.5) C8A(0.5)
 H8A(0.5) C10B(0.5) H10B(0.5) C11B(0.5) H11B(0.5) C7B(0.5) H7B(0.5) C8B(0.5)
 H8B(0.5) C10A(0.5) H10A(0.5) C11A(0.5) H11A(0.5) O14(0.5) H14(0.5) C1(0.5)
 H1A(0.5) H1B(0.5) H1C(0.5) C2(0.5) C5(0.5) H5A(0.5) H5B(0.5) H5C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C9A(H9A), C9A(H9AA), C7A(H7A), C8A(H8A), C10B(H10B),
 C11B(H11B), C7B(H7B), C8B(H8B), C10A(H10A), C11A(H11A), C4(H4), C7(H7), C8(H8),
  C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P12A P 0.50421(3) 0.2500 0.77113(16) 0.0170(2) Uani 1 2 d S T P C .
O13A O 0.51365(8) 0.2500 1.0229(5) 0.0235(6) Uani 1 2 d DS T P . .
O14A O 0.58485(12) 0.1898(3) 1.0164(8) 0.0275(9) Uani 0.5 1 d . . . . .
H14A H 0.5606(9) 0.203(4) 1.037(14) 0.033 Uiso 0.5 1 d DR . . . .
C1A C 0.64083(18) 0.2084(5) 0.8066(13) 0.0364(14) Uani 0.5 1 d D . . . .
H1AA H 0.6527(16) 0.2500 0.704(8) 0.055 Uiso 1 2 d DRS T P . .
H1AB H 0.638(3) 0.147(3) 0.751(16) 0.055 Uiso 0.5 1 d DR . . . .
H1AC H 0.655(2) 0.209(5) 0.948(8) 0.055 Uiso 0.5 1 d DR . . . .
C2A C 0.60191(10) 0.2500 0.8495(7) 0.0207(8) Uani 1 2 d S T P . .
C3A C 0.58080(11) 0.2500 0.6230(7) 0.0189(7) Uani 1 2 d S T P . .
H3A H 0.5961 0.2500 0.4926 0.023 Uiso 1 2 calc RS T P . .
C4A C 0.54370(10) 0.2500 0.5784(6) 0.0191(7) Uani 1 2 d S T P . .
H4A H 0.5375 0.2500 0.4225 0.023 Uiso 1 2 calc RS T P . .
C5A C 0.6054(2) 0.3458(5) 0.9441(12) 0.0339(14) Uani 0.5 1 d D . . . .
H5AA H 0.616(2) 0.387(5) 0.833(12) 0.051 Uiso 0.5 1 d DR . . . .
H5AB H 0.5829(15) 0.375(6) 0.995(16) 0.051 Uiso 0.5 1 d DR . . . .
H5AC H 0.617(2) 0.342(6) 1.094(7) 0.051 Uiso 0.5 1 d DR . . . .
C6A C 0.47688(7) 0.34973(18) 0.6915(5) 0.0194(5) Uani 1 1 d . . . . .
C9A C 0.43497(8) 0.50571(19) 0.5892(6) 0.0283(7) Uani 1 1 d . . . . .
H9A H 0.4205 0.5578 0.5614 0.034 Uiso 0.5 1 calc R . . A 1
H9AA H 0.4206 0.5572 0.5540 0.034 Uiso 0.5 1 calc R . . B 2
C7A C 0.44661(16) 0.3414(4) 0.5347(11) 0.0242(11) Uani 0.5 1 d . . . C 1
H7A H 0.4406 0.2852 0.4677 0.029 Uiso 0.5 1 calc R . . C 1
C8A C 0.42606(17) 0.4203(4) 0.4841(11) 0.0295(13) Uani 0.5 1 d . . . C 1
H8A H 0.4062 0.4171 0.3799 0.035 Uiso 0.5 1 calc R . . C 1
C10B C 0.46562(17) 0.5088(4) 0.7333(11) 0.0292(13) Uani 0.5 1 d . . . C 1
H10B H 0.4730 0.5649 0.7953 0.035 Uiso 0.5 1 calc R . . C 1
C11B C 0.48565(15) 0.4313(4) 0.7881(10) 0.0228(11) Uani 0.5 1 d . . . C 1
H11B H 0.5054 0.4349 0.8927 0.027 Uiso 0.5 1 calc R . . C 1
C7B C 0.47274(15) 0.3832(3) 0.4663(9) 0.0191(10) Uani 0.5 1 d . . . C 2
H7B H 0.4847 0.3532 0.3453 0.023 Uiso 0.5 1 calc R . . C 2
C8B C 0.45101(16) 0.4605(4) 0.4204(11) 0.0256(12) Uani 0.5 1 d . . . C 2
H8B H 0.4478 0.4801 0.2690 0.031 Uiso 0.5 1 calc R . . C 2
C10A C 0.43875(15) 0.4791(4) 0.8255(11) 0.0260(12) Uani 0.5 1 d . . . C 2
H10A H 0.4273 0.5125 0.9429 0.031 Uiso 0.5 1 calc R . . C 2
C11A C 0.46052(15) 0.4004(4) 0.8741(10) 0.0216(11) Uani 0.5 1 d . . . C 2
H11A H 0.4641 0.3818 1.0261 0.026 Uiso 0.5 1 calc R . . C 2
P12 P 0.25603(3) 0.2500 0.90480(17) 0.0216(3) Uani 1 2 d S T P . .
O13 O 0.27632(8) 0.2500 0.6784(5) 0.0292(7) Uani 1 2 d DS T P . .
O14 O 0.33901(13) 0.3405(3) 0.8121(9) 0.0283(10) Uani 0.5 1 d D . . . .
H14 H 0.3203(11) 0.307(4) 0.747(11) 0.034 Uiso 0.5 1 d DR . . . .
C1 C 0.38616(19) 0.3268(5) 1.0944(13) 0.0387(15) Uani 0.5 1 d D . . . .
H1A H 0.3785(11) 0.379(4) 1.185(13) 0.058 Uiso 0.5 1 d DR . . . .
H1B H 0.3964(13) 0.291(3) 1.220(8) 0.058 Uiso 0.5 1 d DR . . . .
H1C H 0.4049(10) 0.342(5) 0.982(6) 0.058 Uiso 0.5 1 d DR . . . .
C2 C 0.35206(16) 0.2784(4) 0.9862(11) 0.0220(12) Uani 0.5 1 d D . . . .
C3 C 0.32236(13) 0.2500 1.1743(8) 0.0365(11) Uani 1 2 d S T P . .
H3 H 0.3320(17) 0.2500 1.331(11) 0.044 Uiso 1 2 d RS T P . .
C4 C 0.28522(12) 0.2500 1.1559(7) 0.0243(8) Uani 1 2 d S T P . .
H4 H 0.2723 0.2500 1.2955 0.029 Uiso 1 2 calc RS T P . .
C5 C 0.3624(2) 0.1864(5) 0.8833(14) 0.0389(16) Uani 0.5 1 d D . . . .
H5A H 0.371(2) 0.143(2) 1.000(7) 0.058 Uiso 0.5 1 d DR . . . .
H5B H 0.3433(17) 0.160(3) 0.787(14) 0.058 Uiso 0.5 1 d DR . . . .
H5C H 0.3818(18) 0.207(5) 0.782(13) 0.058 Uiso 0.5 1 d DR . . . .
C6 C 0.22650(8) 0.3507(2) 0.9315(5) 0.0258(6) Uani 1 1 d . . . . .
C7 C 0.20474(11) 0.3701(3) 1.1261(6) 0.0455(10) Uani 1 1 d . . . . .
H7 H 0.2053 0.3311 1.2531 0.055 Uiso 1 1 calc R . . . .
C8 C 0.18236(14) 0.4478(3) 1.1287(7) 0.0626(14) Uani 1 1 d . . . . .
H8 H 0.1672 0.4598 1.2562 0.075 Uiso 1 1 calc R . . . .
C9 C 0.18223(13) 0.5070(3) 0.9459(7) 0.0526(11) Uani 1 1 d . . . . .
H9 H 0.1671 0.5591 0.9504 0.063 Uiso 1 1 calc R . . . .
C10 C 0.20420(11) 0.4903(2) 0.7558(7) 0.0421(9) Uani 1 1 d . . . . .
H10 H 0.2042 0.5312 0.6328 0.051 Uiso 1 1 calc R . . . .
C11 C 0.22650(9) 0.4116(2) 0.7478(6) 0.0312(7) Uani 1 1 d . . . . .
H11 H 0.2414 0.4000 0.6190 0.037 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
P12A O13A 1.497(3) . ?
P12A C4A 1.793(4) . ?
P12A C6A 1.807(3) 8_565 ?
P12A C6A 1.807(3) . ?
O14A O14A 1.754(9) 8_565 ?
O14A H14A 0.89(3) . ?
O14A C2A 1.439(5) . ?
O14A C5A 0.989(8) 8_565 ?
C1A C1A 1.213(16) 8_565 ?
C1A H1AA 0.95(2) . ?
C1A H1AB 0.95(2) . ?
C1A H1AC 0.95(2) . ?
C1A C2A 1.530(7) . ?
C1A C5A 1.685(10) 8_565 ?
C2A O14A 1.439(5) 8_565 ?
C2A C1A 1.530(7) 8_565 ?
C2A C3A 1.512(5) . ?
C2A C5A 1.504(7) . ?
C2A C5A 1.504(7) 8_565 ?
C3A H3A 0.9300 . ?
C3A C4A 1.342(5) . ?
C4A H4A 0.9300 . ?
C5A O14A 0.989(8) 8_565 ?
C5A C1A 1.685(10) 8_565 ?
C5A H5AA 0.96(2) . ?
C5A H5AB 0.95(2) . ?
C5A H5AC 0.96(2) . ?
C6A C7A 1.413(6) . ?
C6A C11B 1.349(6) . ?
C6A C7B 1.401(6) . ?
C6A C11A 1.415(6) . ?
C9A H9A 0.9300 . ?
C9A H9AA 0.9300 . ?
C9A C8A 1.421(7) . ?
C9A C10B 1.372(7) . ?
C9A C8B 1.310(7) . ?
C9A C10A 1.429(7) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.393(8) . ?
C8A H8A 0.9300 . ?
C10B H10B 0.9300 . ?
C10B C11B 1.372(8) . ?
C11B H11B 0.9300 . ?
C7B H7B 0.9300 . ?
C7B C8B 1.390(7) . ?
C8B H8B 0.9300 . ?
C10A H10A 0.9300 . ?
C10A C11A 1.412(8) . ?
C11A H11A 0.9300 . ?
P12 O13 1.497(3) . ?
P12 C4 1.787(4) . ?
P12 C6 1.809(3) 8_565 ?
P12 C6 1.809(3) . ?
O14 H14 0.909(17) . ?
O14 C2 1.432(7) . ?
O14 C5 1.007(9) 8_565 ?
C1 H1A 0.96(2) . ?
C1 H1B 0.967(19) . ?
C1 H1C 0.958(19) . ?
C1 C2 1.535(9) . ?
C1 C5 1.498(10) 8_565 ?
C2 C2 0.827(11) 8_565 ?
C2 C3 1.572(8) . ?
C2 C5 1.513(9) . ?
C2 C5 0.869(8) 8_565 ?
C3 C2 1.572(8) 8_565 ?
C3 H3 0.97(6) . ?
C3 C4 1.323(6) . ?
C4 H4 0.9300 . ?
C5 O14 1.007(9) 8_565 ?
C5 C1 1.498(10) 8_565 ?
C5 C2 0.869(8) 8_565 ?
C5 C5 1.854(15) 8_565 ?
C5 H5A 0.97(2) . ?
C5 H5B 0.96(2) . ?
C5 H5C 0.95(2) . ?
C6 C7 1.396(5) . ?
C6 C11 1.386(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.366(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(5) . ?
C11 H11 0.9300 . ?

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
O13A P12A C4A 115.59(17) . . ?
O13A P12A C6A 111.67(11) . . ?
O13A P12A C6A 111.67(11) . 8_565 ?
C4A P12A C6A 105.13(11) . . ?
C4A P12A C6A 105.13(11) . 8_565 ?
C6A P12A C6A 107.01(17) 8_565 . ?
O14A O14A H14A 78(4) 8_565 . ?
C2A O14A O14A 52.5(2) . 8_565 ?
C2A O14A H14A 112(5) . . ?
C5A O14A O14A 121.6(5) 8_565 8_565 ?
C5A O14A H14A 152(5) 8_565 . ?
C5A O14A C2A 74.0(5) 8_565 . ?
C1A C1A H1AA 50.3(12) 8_565 . ?
C1A C1A H1AB 160(6) 8_565 . ?
C1A C1A H1AC 90(5) 8_565 . ?
C1A C1A C2A 66.6(3) 8_565 . ?
C1A C1A C5A 117.9(4) 8_565 8_565 ?
H1AA C1A H1AB 116(6) . . ?
H1AA C1A H1AC 108(6) . . ?
H1AB C1A H1AC 110(7) . . ?
C2A C1A H1AA 105(3) . . ?
C2A C1A H1AB 110(6) . . ?
C2A C1A H1AC 109(5) . . ?
C2A C1A C5A 55.6(3) . 8_565 ?
C5A C1A H1AA 158(4) 8_565 . ?
C5A C1A H1AB 69(6) 8_565 . ?
C5A C1A H1AC 89(5) 8_565 . ?
O14A C2A O14A 75.1(4) . 8_565 ?
O14A C2A C1A 104.4(4) 8_565 8_565 ?
O14A C2A C1A 137.0(4) 8_565 . ?
O14A C2A C1A 104.4(4) . . ?
O14A C2A C1A 137.0(4) . 8_565 ?
O14A C2A C3A 112.0(3) 8_565 . ?
O14A C2A C3A 112.0(3) . . ?
O14A C2A C5A 39.2(3) 8_565 . ?
O14A C2A C5A 110.8(4) . . ?
O14A C2A C5A 110.8(4) 8_565 8_565 ?
O14A C2A C5A 39.2(3) . 8_565 ?
C1A C2A C1A 46.7(6) . 8_565 ?
C3A C2A C1A 107.9(4) . 8_565 ?
C3A C2A C1A 107.9(4) . . ?
C5A C2A C1A 67.5(4) 8_565 . ?
C5A C2A C1A 110.6(5) . . ?
C5A C2A C1A 67.5(4) . 8_565 ?
C5A C2A C1A 110.6(5) 8_565 8_565 ?
C5A C2A C3A 110.9(3) . . ?
C5A C2A C3A 110.9(3) 8_565 . ?
C5A C2A C5A 136.1(6) 8_565 . ?
C2A C3A H3A 114.6 . . ?
C4A C3A C2A 130.8(4) . . ?
C4A C3A H3A 114.6 . . ?
P12A C4A H4A 114.8 . . ?
C3A C4A P12A 130.4(3) . . ?
C3A C4A H4A 114.8 . . ?
O14A C5A C1A 120.4(7) 8_565 8_565 ?
O14A C5A C2A 66.8(5) 8_565 . ?
O14A C5A H5AA 155(6) 8_565 . ?
O14A C5A H5AB 59(6) 8_565 . ?
O14A C5A H5AC 84(5) 8_565 . ?
C1A C5A H5AA 71(6) 8_565 . ?
C1A C5A H5AB 169(6) 8_565 . ?
C1A C5A H5AC 96(5) 8_565 . ?
C2A C5A C1A 57.0(4) . 8_565 ?
C2A C5A H5AA 112(6) . . ?
C2A C5A H5AB 117(6) . . ?
C2A C5A H5AC 108(5) . . ?
H5AA C5A H5AB 105(8) . . ?
H5AA C5A H5AC 118(7) . . ?
H5AB C5A H5AC 95(7) . . ?
C7A C6A P12A 120.2(3) . . ?
C11B C6A P12A 118.5(3) . . ?
C11B C6A C7A 121.2(4) . . ?
C7B C6A P12A 125.0(3) . . ?
C7B C6A C11A 118.2(4) . . ?
C11A C6A P12A 116.6(3) . . ?
C8A C9A H9A 121.1 . . ?
C10B C9A H9A 121.1 . . ?
C10B C9A C8A 117.8(4) . . ?
C8B C9A H9AA 118.7 . . ?
C8B C9A C10A 122.6(4) . . ?
C10A C9A H9AA 118.7 . . ?
C6A C7A H7A 121.2 . . ?
C8A C7A C6A 117.6(5) . . ?
C8A C7A H7A 121.2 . . ?
C9A C8A H8A 119.5 . . ?
C7A C8A C9A 121.0(5) . . ?
C7A C8A H8A 119.5 . . ?
C9A C10B H10B 119.2 . . ?
C11B C10B C9A 121.7(5) . . ?
C11B C10B H10B 119.2 . . ?
C6A C11B C10B 120.6(5) . . ?
C6A C11B H11B 119.7 . . ?
C10B C11B H11B 119.7 . . ?
C6A C7B H7B 119.4 . . ?
C8B C7B C6A 121.2(5) . . ?
C8B C7B H7B 119.4 . . ?
C9A C8B C7B 120.4(5) . . ?
C9A C8B H8B 119.8 . . ?
C7B C8B H8B 119.8 . . ?
C9A C10A H10A 121.2 . . ?
C11A C10A C9A 117.6(5) . . ?
C11A C10A H10A 121.2 . . ?
C6A C11A H11A 120.0 . . ?
C10A C11A C6A 119.9(5) . . ?
C10A C11A H11A 120.0 . . ?
O13 P12 C4 115.75(18) . . ?
O13 P12 C6 110.74(12) . . ?
O13 P12 C6 110.74(12) . 8_565 ?
C4 P12 C6 105.46(12) . . ?
C4 P12 C6 105.46(12) . 8_565 ?
C6 P12 C6 108.3(2) 8_565 . ?
C2 O14 H14 101(5) . . ?
C5 O14 H14 124(5) 8_565 . ?
C5 O14 C2 36.8(5) 8_565 . ?
H1A C1 H1B 97(6) . . ?
H1A C1 H1C 113(6) . . ?
H1B C1 H1C 112(3) . . ?
C2 C1 H1A 111(2) . . ?
C2 C1 H1B 111(2) . . ?
C2 C1 H1C 112(2) . . ?
C5 C1 H1A 113(4) 8_565 . ?
C5 C1 H1B 139(3) 8_565 . ?
C5 C1 H1C 82(2) 8_565 . ?
C5 C1 C2 33.3(4) 8_565 . ?
O14 C2 C1 104.6(5) . . ?
O14 C2 C3 116.0(4) . . ?
O14 C2 C5 111.2(5) . . ?
C1 C2 C3 111.5(5) . . ?
C2 C2 O14 129.2(3) 8_565 . ?
C2 C2 C1 117.3(4) 8_565 . ?
C2 C2 C3 74.7(2) 8_565 . ?
C2 C2 C5 126.2(7) 8_565 8_565 ?
C2 C2 C5 27.6(4) 8_565 . ?
C5 C2 O14 43.9(6) 8_565 . ?
C5 C2 C1 112.1(5) . . ?
C5 C2 C1 71.0(7) 8_565 . ?
C5 C2 C3 101.7(4) . . ?
C5 C2 C3 156.3(8) 8_565 . ?
C5 C2 C5 98.6(10) 8_565 . ?
C2 C3 C2 30.5(4) 8_565 . ?
C2 C3 H3 114(3) 8_565 . ?
C2 C3 H3 114(3) . . ?
C4 C3 C2 127.8(4) . . ?
C4 C3 C2 127.8(4) . 8_565 ?
C4 C3 H3 115(4) . . ?
P12 C4 H4 115.0 . . ?
C3 C4 P12 130.1(4) . . ?
C3 C4 H4 115.0 . . ?
O14 C5 C1 138.5(9) 8_565 8_565 ?
O14 C5 C2 107.8(7) 8_565 . ?
O14 C5 C5 112.9(5) 8_565 8_565 ?
O14 C5 H5A 106(5) 8_565 . ?
O14 C5 H5B 12(6) 8_565 . ?
O14 C5 H5C 118(6) 8_565 . ?
C1 C5 C2 85.9(6) 8_565 . ?
C1 C5 C5 97.3(4) 8_565 8_565 ?
C1 C5 H5A 35(4) 8_565 . ?
C1 C5 H5B 146(5) 8_565 . ?
C1 C5 H5C 98(6) 8_565 . ?
C2 C5 O14 99.3(9) 8_565 8_565 ?
C2 C5 C1 75.7(7) 8_565 8_565 ?
C2 C5 C2 26.2(5) 8_565 . ?
C2 C5 C5 53.8(7) 8_565 8_565 ?
C2 C5 C5 27.6(4) . 8_565 ?
C2 C5 H5A 92(3) 8_565 . ?
C2 C5 H5A 112(2) . . ?
C2 C5 H5B 114(2) . . ?
C2 C5 H5B 110(4) 8_565 . ?
C2 C5 H5C 98(5) . . ?
C2 C5 H5C 123(5) 8_565 . ?
C5 C5 H5A 131(3) 8_565 . ?
C5 C5 H5B 113(3) 8_565 . ?
C5 C5 H5C 72(5) 8_565 . ?
H5A C5 H5B 111(3) . . ?
H5A C5 H5C 115(7) . . ?
H5B C5 H5C 106(8) . . ?
C7 C6 P12 123.7(2) . . ?
C11 C6 P12 116.9(2) . . ?
C11 C6 C7 119.4(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.5(4) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C6 C11 C10 120.0(3) . . ?
C6 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?

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
P12A C6A C7A C8A 178.6(4) . . . . ?
P12A C6A C11B C10B -179.8(4) . . . . ?
P12A C6A C7B C8B 179.8(4) . . . . ?
P12A C6A C11A C10A -180.0(4) . . . . ?
O13A P12A C4A C3A 0.000(1) . . . . ?
O13A P12A C6A C7A -139.6(3) . . . . ?
O13A P12A C6A C11B 39.2(4) . . . . ?
O13A P12A C6A C7B 161.0(3) . . . . ?
O13A P12A C6A C11A -14.9(3) . . . . ?
O14A O14A C2A C1A 135.5(4) 8_565 . . . ?
O14A O14A C2A C1A 95.2(6) 8_565 . . 8_565 ?
O14A O14A C2A C3A -108.1(3) 8_565 . . . ?
O14A O14A C2A C5A 155.3(5) 8_565 . . 8_565 ?
O14A O14A C2A C5A 16.4(3) 8_565 . . . ?
O14A C2A C3A C4A 41.1(2) . . . . ?
O14A C2A C3A C4A -41.1(2) 8_565 . . . ?
O14A C2A C5A O14A -25.5(5) . . . 8_565 ?
O14A C2A C5A C1A 159.1(6) 8_565 . . 8_565 ?
O14A C2A C5A C1A 133.6(5) . . . 8_565 ?
C1A C1A C2A O14A -142.7(4) 8_565 . . . ?
C1A C1A C2A O14A -59.3(4) 8_565 . . 8_565 ?
C1A C1A C2A C3A 98.0(2) 8_565 . . . ?
C1A C1A C2A C5A -156.2(3) 8_565 . . 8_565 ?
C1A C1A C2A C5A -23.5(3) 8_565 . . . ?
C1A C2A C3A C4A 155.4(3) . . . . ?
C1A C2A C3A C4A -155.4(3) 8_565 . . . ?
C1A C2A C5A O14A -140.8(5) . . . 8_565 ?
C1A C2A C5A O14A -159.1(6) 8_565 . . 8_565 ?
C1A C2A C5A C1A 18.3(4) . . . 8_565 ?
C2A C3A C4A P12A 0.000(1) . . . . ?
C3A C2A C5A O14A 99.5(5) . . . 8_565 ?
C3A C2A C5A C1A -101.3(4) . . . 8_565 ?
C4A P12A C6A C7A 94.3(4) . . . . ?
C4A P12A C6A C11B -86.8(4) . . . . ?
C4A P12A C6A C7B 34.9(4) . . . . ?
C4A P12A C6A C11A -141.0(3) . . . . ?
C5A O14A C2A O14A -155.3(5) 8_565 . . 8_565 ?
C5A O14A C2A C1A -19.9(6) 8_565 . . . ?
C5A O14A C2A C1A -60.1(7) 8_565 . . 8_565 ?
C5A O14A C2A C3A 96.5(5) 8_565 . . . ?
C5A O14A C2A C5A -139.0(8) 8_565 . . . ?
C5A C1A C2A O14A 13.5(4) 8_565 . . . ?
C5A C1A C2A O14A 96.8(6) 8_565 . . 8_565 ?
C5A C1A C2A C1A 156.2(3) 8_565 . . 8_565 ?
C5A C1A C2A C3A -105.8(3) 8_565 . . . ?
C5A C1A C2A C5A 132.7(7) 8_565 . . . ?
C5A C2A C3A C4A -83.3(4) . . . . ?
C5A C2A C3A C4A 83.3(4) 8_565 . . . ?
C5A C2A C5A O14A -62.3(10) 8_565 . . 8_565 ?
C5A C2A C5A C1A 96.8(9) 8_565 . . 8_565 ?
C6A P12A C4A C3A 123.61(10) . . . . ?
C6A P12A C4A C3A -123.61(10) 8_565 . . . ?
C6A P12A C6A C7A -17.1(4) 8_565 . . . ?
C6A P12A C6A C11B 161.7(3) 8_565 . . . ?
C6A P12A C6A C7B -76.5(4) 8_565 . . . ?
C6A P12A C6A C11A 107.6(3) 8_565 . . . ?
C6A C7A C8A C9A -0.9(9) . . . . ?
C6A C7B C8B C9A 2.5(8) . . . . ?
C9A C10B C11B C6A 3.5(9) . . . . ?
C9A C10A C11A C6A -1.5(7) . . . . ?
C7A C6A C11B C10B -1.0(8) . . . . ?
C7A C6A C7B C8B 77.6(6) . . . . ?
C7A C6A C11A C10A -46.6(6) . . . . ?
C8A C9A C10B C11B -4.5(8) . . . . ?
C8A C9A C8B C7B -75.0(6) . . . . ?
C8A C9A C10A C11A 46.9(6) . . . . ?
C10B C9A C8A C7A 3.2(8) . . . . ?
C10B C9A C8B C7B 46.1(6) . . . . ?
C10B C9A C10A C11A -70.2(5) . . . . ?
C11B C6A C7A C8A -0.2(8) . . . . ?
C11B C6A C7B C8B -48.9(6) . . . . ?
C11B C6A C11A C10A 74.7(6) . . . . ?
C7B C6A C7A C8A -69.4(6) . . . . ?
C7B C6A C11B C10B 44.6(6) . . . . ?
C7B C6A C11A C10A 3.9(6) . . . . ?
C8B C9A C8A C7A 77.0(7) . . . . ?
C8B C9A C10B C11B -50.9(7) . . . . ?
C8B C9A C10A C11A -0.5(7) . . . . ?
C10A C9A C8A C7A -46.9(7) . . . . ?
C10A C9A C10B C11B 76.3(6) . . . . ?
C10A C9A C8B C7B 0.1(7) . . . . ?
C11A C6A C7A C8A 47.3(6) . . . . ?
C11A C6A C11B C10B -78.6(6) . . . . ?
C11A C6A C7B C8B -4.4(6) . . . . ?
P12 C6 C7 C8 -178.5(3) . . . . ?
P12 C6 C11 C10 179.5(2) . . . . ?
O13 P12 C4 C3 0.000(1) . . . . ?
O13 P12 C6 C7 -178.8(3) . . . . ?
O13 P12 C6 C11 0.1(3) . . . . ?
O14 C2 C3 C2 126.6(4) . . . 8_565 ?
O14 C2 C3 C4 24.4(6) . . . . ?
O14 C2 C5 O14 -61.8(8) . . . 8_565 ?
O14 C2 C5 C1 158.2(6) . . . 8_565 ?
O14 C2 C5 C2 -136.2(6) . . . 8_565 ?
O14 C2 C5 C5 43.8(6) . . . 8_565 ?
C1 C2 C3 C2 -113.8(4) . . . 8_565 ?
C1 C2 C3 C4 144.0(4) . . . . ?
C1 C2 C5 O14 -178.5(7) . . . 8_565 ?
C1 C2 C5 C1 41.5(6) . . . 8_565 ?
C1 C2 C5 C2 107.1(8) . . . 8_565 ?
C1 C2 C5 C5 -73.0(8) . . . 8_565 ?
C2 C2 C3 C4 -102.2(3) 8_565 . . . ?
C2 C2 C5 O14 74.4(9) 8_565 . . 8_565 ?
C2 C2 C5 C1 -65.5(7) 8_565 . . 8_565 ?
C2 C2 C5 C5 179.997(10) 8_565 . . 8_565 ?
C2 C3 C4 P12 -19.4(3) 8_565 . . . ?
C2 C3 C4 P12 19.4(3) . . . . ?
C3 C2 C5 O14 62.3(8) . . . 8_565 ?
C3 C2 C5 C1 -77.7(5) . . . 8_565 ?
C3 C2 C5 C2 -12.2(9) . . . 8_565 ?
C3 C2 C5 C5 167.8(9) . . . 8_565 ?
C4 P12 C6 C7 -52.8(3) . . . . ?
C4 P12 C6 C11 126.0(2) . . . . ?
C5 O14 C2 C1 41.0(9) 8_565 . . . ?
C5 O14 C2 C2 -104.7(9) 8_565 . . 8_565 ?
C5 O14 C2 C3 164.2(10) 8_565 . . . ?
C5 O14 C2 C5 -80.2(11) 8_565 . . . ?
C5 C1 C2 O14 -28.8(7) 8_565 . . . ?
C5 C1 C2 C2 121.7(7) 8_565 . . 8_565 ?
C5 C1 C2 C3 -154.9(9) 8_565 . . . ?
C5 C1 C2 C5 91.8(10) 8_565 . . . ?
C5 C2 C3 C2 154.5(19) 8_565 . . 8_565 ?
C5 C2 C3 C2 5.8(4) . . . 8_565 ?
C5 C2 C3 C4 -96.4(4) . . . . ?
C5 C2 C3 C4 52(2) 8_565 . . . ?
C5 C2 C5 O14 -105.6(9) 8_565 . . 8_565 ?
C5 C2 C5 C1 114.5(7) 8_565 . . 8_565 ?
C5 C2 C5 C2 180.003(10) 8_565 . . 8_565 ?
C6 P12 C4 C3 -122.77(11) . . . . ?
C6 P12 C4 C3 122.77(11) 8_565 . . . ?
C6 P12 C6 C7 59.6(4) 8_565 . . . ?
C6 P12 C6 C11 -121.5(2) 8_565 . . . ?
C6 C7 C8 C9 -2.0(7) . . . . ?
C7 C6 C11 C10 -1.6(5) . . . . ?
C7 C8 C9 C10 0.3(7) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C9 C10 C11 C6 -0.1(5) . . . . ?
C11 C6 C7 C8 2.6(6) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1029399'
#######################################################################
#
#                 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_asb_315_2
_audit_creation_date             2014-02-04
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H18 Br O2 P'
_chemical_formula_sum            'C17 H18 Br O2 P'
_chemical_formula_weight         365.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Br P O2 C10 H20'
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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.3200(4)
_cell_length_b                   8.3517(5)
_cell_length_c                   11.5876(6)
_cell_angle_alpha                96.038(4)
_cell_angle_beta                 90.854(4)
_cell_angle_gamma                100.324(5)
_cell_volume                     787.27(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5614
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6350
_cell_measurement_theta_min      2.9890
_exptl_absorpt_coefficient_mu    2.714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12614
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.90
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -75.00  -49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -57.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   22.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -94.00  -42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega   39.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  178.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega   -7.00   82.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   38.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  7 omega  -53.00   44.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -38.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
  8 omega  -24.00    9.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
  9 omega   33.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -99.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 10 omega  -50.00   12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -57.0000  150.0000 62

#__ type_ start__ end____ width___ exp.time_
 11 omega    3.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -99.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   -2.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   57.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 13 omega  -25.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   19.0000  120.0000 117
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0252771000
_diffrn_orient_matrix_UB_12      -0.0116603000
_diffrn_orient_matrix_UB_13      -0.0579948000
_diffrn_orient_matrix_UB_21      0.0681817000
_diffrn_orient_matrix_UB_22      0.0641464000
_diffrn_orient_matrix_UB_23      0.0130293000
_diffrn_orient_matrix_UB_31      0.0472273000
_diffrn_orient_matrix_UB_32      -0.0573780000
_diffrn_orient_matrix_UB_33      0.0161308000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3163
_reflns_number_total             3546
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0219P)²+0.2725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0590
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Br18 Br 0.92703(2) 0.49367(2) 0.845886(18) 0.01774(7) Uani 1 1 d . . .
P19 P 0.76297(5) 0.75008(6) 0.73033(4) 0.01127(11) Uani 1 1 d . . .
O20 O 0.75217(15) 0.82197(15) 0.61850(12) 0.0146(3) Uani 1 1 d . . .
O21 O 1.07390(15) 0.96108(15) 0.62681(13) 0.0159(3) Uani 1 1 d . . .
H21 H 0.9759 0.9439 0.6097 0.024 Uiso 1 1 calc R . .
C1 C 1.0871(2) 0.7373(2) 0.47590(18) 0.0182(4) Uani 1 1 d . . .
H1A H 0.9702 0.7183 0.4665 0.027 Uiso 1 1 calc R . .
H1B H 1.1249 0.6351 0.4618 0.027 Uiso 1 1 calc R . .
H1C H 1.1346 0.8100 0.4217 0.027 Uiso 1 1 calc R . .
C2 C 1.1374(2) 0.8141(2) 0.59940(18) 0.0138(4) Uani 1 1 d . . .
C3 C 1.0833(2) 0.6883(2) 0.68377(17) 0.0129(4) Uani 1 1 d . . .
H3 H 1.1574 0.6202 0.6965 0.016 Uiso 1 1 calc R . .
C4 C 0.9464(2) 0.6611(2) 0.74199(17) 0.0120(4) Uani 1 1 d . . .
C5 C 1.3227(2) 0.8665(2) 0.6119(2) 0.0200(4) Uani 1 1 d . . .
H5A H 1.3590 0.9440 0.5580 0.030 Uiso 1 1 calc R . .
H5B H 1.3735 0.7724 0.5960 0.030 Uiso 1 1 calc R . .
H5C H 1.3523 0.9162 0.6896 0.030 Uiso 1 1 calc R . .
C6 C 0.7567(2) 0.8969(2) 0.85509(17) 0.0124(4) Uani 1 1 d . . .
C7 C 0.6872(2) 1.0333(2) 0.83526(18) 0.0153(4) Uani 1 1 d . . .
H7 H 0.6532 1.0468 0.7606 0.018 Uiso 1 1 calc R . .
C8 C 0.6696(2) 1.1483(2) 0.92811(19) 0.0179(4) Uani 1 1 d . . .
H8 H 0.6222 1.2381 0.9157 0.021 Uiso 1 1 calc R . .
C9 C 0.7224(2) 1.1292(2) 1.03868(19) 0.0187(4) Uani 1 1 d . . .
H9 H 0.7105 1.2065 1.1003 0.022 Uiso 1 1 calc R . .
C10 C 0.7931(2) 0.9958(2) 1.05843(18) 0.0178(4) Uani 1 1 d . . .
H10 H 0.8294 0.9844 1.1329 0.021 Uiso 1 1 calc R . .
C11 C 0.8093(2) 0.8797(2) 0.96698(18) 0.0151(4) Uani 1 1 d . . .
H11 H 0.8557 0.7896 0.9804 0.018 Uiso 1 1 calc R . .
C12 C 0.5946(2) 0.5830(2) 0.74077(17) 0.0124(4) Uani 1 1 d . . .
C13 C 0.5030(2) 0.5655(2) 0.83973(17) 0.0137(4) Uani 1 1 d . . .
H13 H 0.5316 0.6381 0.9064 0.016 Uiso 1 1 calc R . .
C14 C 0.3683(2) 0.4389(2) 0.83861(18) 0.0173(4) Uani 1 1 d . . .
H14 H 0.3066 0.4279 0.9045 0.021 Uiso 1 1 calc R . .
C15 C 0.3262(2) 0.3298(2) 0.74020(19) 0.0183(4) Uani 1 1 d . . .
H15 H 0.2363 0.2457 0.7402 0.022 Uiso 1 1 calc R . .
C16 C 0.4174(2) 0.3453(2) 0.64151(19) 0.0188(4) Uani 1 1 d . . .
H16 H 0.3891 0.2717 0.5753 0.023 Uiso 1 1 calc R . .
C17 C 0.5515(2) 0.4718(2) 0.64207(18) 0.0165(4) Uani 1 1 d . . .
H17 H 0.6130 0.4822 0.5760 0.020 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
Br18 C4 1.9258(18) . ?
P19 O20 1.4923(14) . ?
P19 C4 1.8224(18) . ?
P19 C6 1.803(2) . ?
P19 C12 1.8066(18) . ?
O21 C2 1.429(2) . ?
C1 C2 1.526(3) . ?
C2 C3 1.524(2) . ?
C2 C5 1.526(3) . ?
C3 C4 1.329(3) . ?
C6 C7 1.404(3) . ?
C6 C11 1.392(3) . ?
C7 C8 1.392(3) . ?
C8 C9 1.383(3) . ?
C9 C10 1.387(3) . ?
C10 C11 1.385(3) . ?
C12 C13 1.392(3) . ?
C12 C17 1.394(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.391(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O20 P19 C4 111.91(8) . . ?
O20 P19 C6 112.51(8) . . ?
O20 P19 C12 110.98(8) . . ?
C6 P19 C4 109.12(9) . . ?
C6 P19 C12 106.80(9) . . ?
C12 P19 C4 105.13(8) . . ?
O21 C2 C1 111.31(15) . . ?
O21 C2 C3 112.20(15) . . ?
O21 C2 C5 105.11(14) . . ?
C1 C2 C5 110.48(16) . . ?
C3 C2 C1 109.16(15) . . ?
C3 C2 C5 108.49(16) . . ?
C4 C3 C2 129.85(16) . . ?
P19 C4 Br18 113.58(9) . . ?
C3 C4 Br18 117.24(13) . . ?
C3 C4 P19 129.00(14) . . ?
C7 C6 P19 115.80(15) . . ?
C11 C6 P19 124.53(14) . . ?
C11 C6 C7 119.62(18) . . ?
C8 C7 C6 119.53(19) . . ?
C9 C8 C7 120.11(18) . . ?
C8 C9 C10 120.55(19) . . ?
C11 C10 C9 119.82(19) . . ?
C10 C11 C6 120.36(17) . . ?
C13 C12 P19 123.22(15) . . ?
C13 C12 C17 119.34(17) . . ?
C17 C12 P19 117.37(14) . . ?
C12 C13 C14 119.83(19) . . ?
C15 C14 C13 120.38(19) . . ?
C14 C15 C16 120.23(18) . . ?
C15 C16 C17 119.59(19) . . ?
C16 C17 C12 120.62(18) . . ?

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
P19 C6 C7 C8 176.61(14) . . . . ?
P19 C6 C11 C10 -177.18(14) . . . . ?
P19 C12 C13 C14 175.95(14) . . . . ?
P19 C12 C17 C16 -176.36(14) . . . . ?
O20 P19 C4 Br18 -155.81(9) . . . . ?
O20 P19 C4 C3 19.3(2) . . . . ?
O20 P19 C6 C7 21.49(16) . . . . ?
O20 P19 C6 C11 -161.07(15) . . . . ?
O20 P19 C12 C13 -133.81(15) . . . . ?
O20 P19 C12 C17 43.13(16) . . . . ?
O21 C2 C3 C4 31.0(3) . . . . ?
C1 C2 C3 C4 -92.8(2) . . . . ?
C2 C3 C4 Br18 -177.75(16) . . . . ?
C2 C3 C4 P19 7.3(3) . . . . ?
C4 P19 C6 C7 146.33(13) . . . . ?
C4 P19 C6 C11 -36.23(18) . . . . ?
C4 P19 C12 C13 105.01(16) . . . . ?
C4 P19 C12 C17 -78.05(15) . . . . ?
C5 C2 C3 C4 146.7(2) . . . . ?
C6 P19 C4 Br18 79.01(11) . . . . ?
C6 P19 C4 C3 -105.92(19) . . . . ?
C6 P19 C12 C13 -10.85(17) . . . . ?
C6 P19 C12 C17 166.09(14) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C7 C6 C11 C10 0.2(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C6 0.7(3) . . . . ?
C11 C6 C7 C8 -1.0(3) . . . . ?
C12 P19 C4 Br18 -35.24(12) . . . . ?
C12 P19 C4 C3 139.83(18) . . . . ?
C12 P19 C6 C7 -100.51(14) . . . . ?
C12 P19 C6 C11 76.93(17) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C12 C17 C16 0.7(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C17 C12 C13 C14 -0.9(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1026528'
#######################################################################
#
#                 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_ed_22
_audit_creation_date             2014-10-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H23 O2 P'
_chemical_formula_sum            'C23 H23 O2 P'
_chemical_formula_weight         362.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P O2 C25 H20'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.58114(14)
_cell_length_b                   17.2730(2)
_cell_length_c                   11.63272(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.4889(14)
_cell_angle_gamma                90.00
_cell_volume                     1904.07(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6751
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9290
_cell_measurement_theta_min      4.6280
_exptl_absorpt_coefficient_mu    1.380
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11157
_diffrn_reflns_theta_full        72.45
_diffrn_reflns_theta_max         72.45
_diffrn_reflns_theta_min         4.62
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -106.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   30.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega   63.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega    6.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  5 omega  136.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
  7 omega   55.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
  8 omega   98.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   89.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
 10 omega   77.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega  110.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
 12 omega   72.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   44.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -69.0000 -145.0000 40

#__ type_ start__ end____ width___ exp.time_
 14 omega  120.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 15 omega  129.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
 16 omega   59.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   86.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 19 omega   84.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   44.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
 22 omega   72.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   36.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
 24 omega  153.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   30.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0392613000
_diffrn_orient_matrix_UB_12      -0.0131288000
_diffrn_orient_matrix_UB_13      -0.1318006000
_diffrn_orient_matrix_UB_21      -0.1038441000
_diffrn_orient_matrix_UB_22      0.0685185000
_diffrn_orient_matrix_UB_23      -0.0069513000
_diffrn_orient_matrix_UB_31      0.1188051000
_diffrn_orient_matrix_UB_32      0.0555415000
_diffrn_orient_matrix_UB_33      -0.0225669000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3479
_reflns_number_total             3751
_reflns_odcompleteness_completeness 93.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0459P)²+0.9906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0892
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C22(H22), C2(H2), C26(H26), C23(H23), C17(H17), C10(H10), C19(H19),
 C14(H14), C12(H12), C20(H20), C25(H25), C13(H13), C24(H24), C18(H18), C11(H11)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
P7 P 0.94524(3) 0.635293(17) 0.25736(3) 0.01171(10) Uani 1 d . . .
O8 O 1.05846(9) 0.69444(5) 0.25141(8) 0.0156(2) Uani 1 d . . .
O6 O 1.29267(10) 0.62694(5) 0.35259(8) 0.0189(2) Uani 1 d . . .
H6 H 1.2273 0.6564 0.3296 0.028 Uiso 1 calc . . GR
C1 C 1.01081(13) 0.53682(7) 0.27542(10) 0.0133(2) Uani 1 d . . .
C9 C 0.85113(14) 0.65665(7) 0.37737(11) 0.0145(3) Uani 1 d . . .
C21 C 0.90029(13) 0.47480(7) 0.27254(11) 0.0145(3) Uani 1 d . . .
C16 C 0.69670(13) 0.59397(7) 0.10030(11) 0.0160(3) Uani 1 d . . .
H16 H 0.6697 0.5613 0.1567 0.019 Uiso 1 calc . . R
C22 C 0.82767(14) 0.46248(8) 0.36643(11) 0.0170(3) Uani 1 d . . .
H22 H 0.8437 0.4949 0.4309 0.020 Uiso 1 calc . . R
C2 C 1.14586(13) 0.51464(7) 0.28030(11) 0.0148(3) Uani 1 d . . .
H2 H 1.1583 0.4613 0.2843 0.018 Uiso 1 calc . . R
C26 C 0.87314(14) 0.42633(8) 0.17534(12) 0.0187(3) Uani 1 d . . .
H26 H 0.9206 0.4342 0.1121 0.022 Uiso 1 calc . . R
C3 C 1.28298(13) 0.55962(8) 0.28058(11) 0.0166(3) Uani 1 d . . .
C15 C 0.82410(13) 0.63514(7) 0.12252(11) 0.0139(3) Uani 1 d . . .
C23 C 0.73136(14) 0.40199(8) 0.36410(12) 0.0199(3) Uani 1 d . . .
H23 H 0.6843 0.3937 0.4274 0.024 Uiso 1 calc . . R
C17 C 0.61098(14) 0.60223(8) -0.00651(12) 0.0188(3) Uani 1 d . . .
H17 H 0.5255 0.5759 -0.0207 0.023 Uiso 1 calc . . R
C10 C 0.93610(14) 0.67492(8) 0.48244(12) 0.0193(3) Uani 1 d . . .
H10 H 1.0338 0.6742 0.4872 0.023 Uiso 1 calc . . R
C19 C 0.78090(16) 0.68795(8) -0.07216(12) 0.0218(3) Uani 1 d . . .
H19 H 0.8101 0.7181 -0.1305 0.026 Uiso 1 calc . . R
C4 C 1.40469(14) 0.50768(8) 0.33314(13) 0.0233(3) Uani 1 d . . .
H4A H 1.4921 0.5353 0.3361 0.035 Uiso 1 calc . . GR
H4B H 1.4070 0.4622 0.2860 0.035 Uiso 1 calc . . GR
H4C H 1.3915 0.4929 0.4104 0.035 Uiso 1 calc . . GR
C14 C 0.70497(14) 0.65817(8) 0.37137(12) 0.0177(3) Uani 1 d . . .
H14 H 0.6478 0.6470 0.3016 0.021 Uiso 1 calc . . R
C12 C 0.72847(16) 0.69450(8) 0.57320(12) 0.0221(3) Uani 1 d . . .
H12 H 0.6875 0.7069 0.6385 0.027 Uiso 1 calc . . R
C20 C 0.86566(14) 0.68134(8) 0.03485(12) 0.0181(3) Uani 1 d . . .
H20 H 0.9509 0.7079 0.0484 0.022 Uiso 1 calc . . R
C25 C 0.77568(15) 0.36648(8) 0.17273(13) 0.0221(3) Uani 1 d . . .
H25 H 0.7575 0.3348 0.1076 0.027 Uiso 1 calc . . R
C13 C 0.64396(15) 0.67631(8) 0.46947(12) 0.0205(3) Uani 1 d . . .
H13 H 0.5463 0.6762 0.4654 0.025 Uiso 1 calc . . R
C5 C 1.29762(15) 0.58181(9) 0.15553(12) 0.0223(3) Uani 1 d . . .
H5A H 1.2229 0.6167 0.1256 0.033 Uiso 1 calc . . GR
H5B H 1.2921 0.5360 0.1082 0.033 Uiso 1 calc . . GR
H5C H 1.3870 0.6067 0.1543 0.033 Uiso 1 calc . . GR
C24 C 0.70534(14) 0.35399(8) 0.26750(13) 0.0214(3) Uani 1 d . . .
H24 H 0.6410 0.3136 0.2662 0.026 Uiso 1 calc . . R
C18 C 0.65247(15) 0.64953(8) -0.09202(12) 0.0214(3) Uani 1 d . . .
H18 H 0.5940 0.6554 -0.1627 0.026 Uiso 1 calc . . R
C11 C 0.87450(16) 0.69414(8) 0.57951(12) 0.0230(3) Uani 1 d . . .
H11 H 0.9311 0.7068 0.6489 0.028 Uiso 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
P7 O8 1.4992(9) . ?
P7 C1 1.8147(13) . ?
P7 C9 1.8082(13) . ?
P7 C15 1.8083(13) . ?
O6 C3 1.4281(15) . ?
C1 C21 1.5032(17) . ?
C1 C2 1.3426(18) . ?
C9 C10 1.4009(18) . ?
C9 C14 1.3920(18) . ?
C21 C22 1.3953(18) . ?
C21 C26 1.4001(18) . ?
C16 C15 1.4033(18) . ?
C16 C17 1.3919(18) . ?
C22 C23 1.3915(19) . ?
C2 C3 1.5259(17) . ?
C26 C25 1.3904(19) . ?
C3 C4 1.5258(18) . ?
C3 C5 1.5307(18) . ?
C15 C20 1.3984(18) . ?
C23 C24 1.389(2) . ?
C17 C18 1.390(2) . ?
C10 C11 1.3893(19) . ?
C19 C20 1.387(2) . ?
C19 C18 1.387(2) . ?
C14 C13 1.3925(18) . ?
C12 C13 1.386(2) . ?
C12 C11 1.390(2) . ?
C25 C24 1.391(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
O8 P7 C1 113.80(5) . . ?
O8 P7 C9 110.08(6) . . ?
O8 P7 C15 109.70(6) . . ?
C9 P7 C1 107.78(6) . . ?
C9 P7 C15 109.91(6) . . ?
C15 P7 C1 105.43(6) . . ?
C21 C1 P7 115.77(9) . . ?
C2 C1 P7 125.97(10) . . ?
C2 C1 C21 117.96(11) . . ?
C10 C9 P7 115.33(10) . . ?
C14 C9 P7 125.29(10) . . ?
C14 C9 C10 119.35(12) . . ?
C22 C21 C1 121.49(11) . . ?
C22 C21 C26 119.10(12) . . ?
C26 C21 C1 119.37(11) . . ?
C17 C16 C15 119.68(12) . . ?
C23 C22 C21 120.34(12) . . ?
C1 C2 C3 132.75(12) . . ?
C25 C26 C21 120.42(13) . . ?
O6 C3 C2 113.41(10) . . ?
O6 C3 C4 105.31(10) . . ?
O6 C3 C5 110.27(11) . . ?
C2 C3 C5 108.97(11) . . ?
C4 C3 C2 107.96(11) . . ?
C4 C3 C5 110.87(11) . . ?
C16 C15 P7 126.16(10) . . ?
C20 C15 P7 114.60(10) . . ?
C20 C15 C16 119.24(12) . . ?
C24 C23 C22 120.21(13) . . ?
C18 C17 C16 120.38(12) . . ?
C11 C10 C9 120.07(13) . . ?
C20 C19 C18 119.84(13) . . ?
C9 C14 C13 120.27(12) . . ?
C13 C12 C11 119.92(13) . . ?
C19 C20 C15 120.63(13) . . ?
C26 C25 C24 120.03(13) . . ?
C12 C13 C14 120.16(13) . . ?
C23 C24 C25 119.89(12) . . ?
C19 C18 C17 120.16(13) . . ?
C10 C11 C12 120.21(13) . . ?

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
P7 C1 C21 C22 -75.09(14) . . . . ?
P7 C1 C21 C26 107.34(12) . . . . ?
P7 C1 C2 C3 4.3(2) . . . . ?
P7 C9 C10 C11 178.42(11) . . . . ?
P7 C9 C14 C13 -179.24(10) . . . . ?
P7 C15 C20 C19 -178.49(10) . . . . ?
O8 P7 C1 C21 -175.43(8) . . . . ?
O8 P7 C1 C2 -1.85(13) . . . . ?
O8 P7 C9 C10 -45.85(11) . . . . ?
O8 P7 C9 C14 132.30(11) . . . . ?
O8 P7 C15 C16 -172.46(11) . . . . ?
O8 P7 C15 C20 7.40(11) . . . . ?
C1 P7 C9 C10 78.80(11) . . . . ?
C1 P7 C9 C14 -103.05(12) . . . . ?
C1 P7 C15 C16 64.61(12) . . . . ?
C1 P7 C15 C20 -115.52(10) . . . . ?
C1 C21 C22 C23 -176.50(12) . . . . ?
C1 C21 C26 C25 177.28(12) . . . . ?
C1 C2 C3 O6 42.29(19) . . . . ?
C1 C2 C3 C4 158.57(14) . . . . ?
C1 C2 C3 C5 -80.94(17) . . . . ?
C9 P7 C1 C21 62.19(10) . . . . ?
C9 P7 C1 C2 -124.23(11) . . . . ?
C9 P7 C15 C16 -51.30(12) . . . . ?
C9 P7 C15 C20 128.57(10) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C9 C14 C13 C12 1.3(2) . . . . ?
C21 C1 C2 C3 177.79(12) . . . . ?
C21 C22 C23 C24 -0.9(2) . . . . ?
C21 C26 C25 C24 -0.6(2) . . . . ?
C16 C15 C20 C19 1.39(19) . . . . ?
C16 C17 C18 C19 1.0(2) . . . . ?
C22 C21 C26 C25 -0.35(19) . . . . ?
C22 C23 C24 C25 -0.1(2) . . . . ?
C2 C1 C21 C22 110.79(14) . . . . ?
C2 C1 C21 C26 -66.78(16) . . . . ?
C26 C21 C22 C23 1.07(19) . . . . ?
C26 C25 C24 C23 0.8(2) . . . . ?
C15 P7 C1 C21 -55.17(10) . . . . ?
C15 P7 C1 C2 118.41(12) . . . . ?
C15 P7 C9 C10 -166.79(10) . . . . ?
C15 P7 C9 C14 11.36(13) . . . . ?
C15 C16 C17 C18 1.51(19) . . . . ?
C17 C16 C15 P7 177.16(10) . . . . ?
C17 C16 C15 C20 -2.70(19) . . . . ?
C10 C9 C14 C13 -1.2(2) . . . . ?
C14 C9 C10 C11 0.1(2) . . . . ?
C20 C19 C18 C17 -2.4(2) . . . . ?
C13 C12 C11 C10 -0.6(2) . . . . ?
C18 C19 C20 C15 1.1(2) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1029400'
#######################################################################
#
#                 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_asb8838
_audit_creation_date             2014-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C34 H36 O4 P2), H2 O'
_chemical_formula_sum            'C68 H74 O9 P4'
_chemical_formula_weight         1159.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H30 O4 P2'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.8596(4)
_cell_length_b                   17.6855(6)
_cell_length_c                   18.0481(7)
_cell_angle_alpha                63.547(4)
_cell_angle_beta                 75.760(3)
_cell_angle_gamma                89.150(3)
_cell_volume                     2990.03(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9346
_cell_measurement_temperature    58(60)
_cell_measurement_theta_max      31.8499
_cell_measurement_theta_min      2.5333
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25151
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.54
_diffrn_ambient_temperature      58(60)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9785
_diffrn_measured_fraction_theta_max 0.9785
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -75.00  -38.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661  -57.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega  -65.00  -22.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661   98.0000  -94.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   67.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   92.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   77.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00   94.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   57.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   67.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -98.0000  -21.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega   12.00   62.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   19.0000  -90.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0456930000
_diffrn_orient_matrix_UB_12      -0.0361017000
_diffrn_orient_matrix_UB_13      0.0264628000
_diffrn_orient_matrix_UB_21      -0.0468436000
_diffrn_orient_matrix_UB_22      0.0224325000
_diffrn_orient_matrix_UB_23      -0.0199883000
_diffrn_orient_matrix_UB_31      0.0177053000
_diffrn_orient_matrix_UB_32      -0.0149795000
_diffrn_orient_matrix_UB_33      -0.0312326000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                9974
_reflns_number_total             12734
_reflns_odcompleteness_completeness 96.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.963
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     745
_refine_ls_number_reflns         12734
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0575P)²+1.7821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1257
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
P27 P 0.71479(5) 0.84257(3) 0.56676(3) 0.01224(12) Uani 1 1 d . . .
P27A P 0.23539(5) 0.19700(3) 0.76572(3) 0.01225(12) Uani 1 1 d . . .
P13A P 0.29324(5) 0.31326(3) 0.91031(3) 0.01268(12) Uani 1 1 d . . .
P13 P 0.91153(5) 0.64413(4) 0.69925(3) 0.01389(12) Uani 1 1 d . . .
O28A O 0.17872(14) 0.24102(10) 0.69185(9) 0.0176(3) Uani 1 1 d . . .
O14A O 0.39453(14) 0.30648(10) 0.95546(9) 0.0175(3) Uani 1 1 d . . .
O12A O 0.30758(15) 0.15489(10) 1.08967(9) 0.0180(3) Uani 1 1 d . . .
H H 0.3410 0.2038 1.0584 0.027 Uiso 1 1 calc R . .
O28 O 0.69952(14) 0.90072(10) 0.60773(10) 0.0183(3) Uani 1 1 d . . .
O11A O -0.06518(14) 0.19783(10) 0.78794(10) 0.0188(3) Uani 1 1 d . . .
HA H -0.0015 0.2124 0.7471 0.028 Uiso 1 1 calc R . .
O12 O 0.90568(15) 0.52234(10) 0.60505(9) 0.0192(3) Uani 1 1 d . . .
H12 H 0.9511 0.5337 0.6297 0.029 Uiso 1 1 calc R . .
O14 O 1.01646(14) 0.59691(10) 0.67541(10) 0.0205(3) Uani 1 1 d . . .
O11 O 0.46453(15) 0.81157(11) 0.69562(10) 0.0232(4) Uani 1 1 d . . .
H11 H 0.5227 0.8477 0.6831 0.035 Uiso 1 1 calc R . .
C6 C 0.80914(19) 0.65653(13) 0.56545(13) 0.0142(4) Uani 1 1 d . . .
H6 H 0.7522 0.6829 0.5332 0.017 Uiso 1 1 calc R . .
C5A C 0.24250(18) 0.21262(13) 0.91541(12) 0.0116(4) Uani 1 1 d . . .
C4 C 0.70447(19) 0.73169(13) 0.64594(13) 0.0132(4) Uani 1 1 d . . .
C15 C 0.8091(2) 0.57925(14) 0.80542(13) 0.0158(4) Uani 1 1 d . . .
C21 C 0.9761(2) 0.73929(14) 0.69652(13) 0.0155(4) Uani 1 1 d . . .
C4A C 0.16243(19) 0.21906(13) 0.85548(13) 0.0118(4) Uani 1 1 d . . .
C29 C 0.5932(2) 0.84673(14) 0.51314(13) 0.0160(4) Uani 1 1 d . . .
C7 C 0.8888(2) 0.59879(14) 0.53506(13) 0.0161(4) Uani 1 1 d . . .
C6A C 0.26528(19) 0.13625(14) 0.97057(13) 0.0137(4) Uani 1 1 d . . .
HB H 0.2343 0.0919 0.9634 0.016 Uiso 1 1 calc R . .
C5 C 0.80462(19) 0.67703(13) 0.62926(13) 0.0130(4) Uani 1 1 d . . .
C15A C 0.1465(2) 0.34343(14) 0.95809(13) 0.0143(4) Uani 1 1 d . . .
C2A C -0.0653(2) 0.25091(14) 0.82885(14) 0.0159(4) Uani 1 1 d . . .
C20A C 0.0794(2) 0.28578(14) 1.04172(13) 0.0152(4) Uani 1 1 d . . .
HC H 0.1110 0.2346 1.0702 0.018 Uiso 1 1 calc R . .
C3A C 0.04246(19) 0.23924(13) 0.87206(13) 0.0136(4) Uani 1 1 d . . .
HD H 0.0204 0.2480 0.9206 0.016 Uiso 1 1 calc R . .
C29A C 0.2181(2) 0.08258(14) 0.80889(13) 0.0144(4) Uani 1 1 d . . .
C30A C 0.1091(2) 0.03342(15) 0.87287(14) 0.0186(5) Uani 1 1 d . . .
HE H 0.0468 0.0591 0.8963 0.022 Uiso 1 1 calc R . .
C35A C 0.4052(2) 0.22948(14) 0.73336(14) 0.0165(5) Uani 1 1 d . . .
C21A C 0.3480(2) 0.39257(14) 0.79907(13) 0.0167(4) Uani 1 1 d . . .
C35 C 0.8646(2) 0.87091(13) 0.48586(13) 0.0140(4) Uani 1 1 d . . .
C26 C 0.9053(2) 0.79233(14) 0.72506(13) 0.0171(4) Uani 1 1 d . . .
H26 H 0.8170 0.7799 0.7470 0.020 Uiso 1 1 calc R . .
C38 C 1.0980(2) 0.92329(14) 0.36143(14) 0.0191(5) Uani 1 1 d . . .
H38 H 1.1762 0.9402 0.3200 0.023 Uiso 1 1 calc R . .
C7A C 0.3315(2) 0.10661(14) 1.04284(14) 0.0168(4) Uani 1 1 d . . .
C39 C 0.9942(2) 0.89204(14) 0.34747(14) 0.0183(5) Uani 1 1 d . . .
H39 H 1.0026 0.8889 0.2964 0.022 Uiso 1 1 calc R . .
C25 C 0.9653(2) 0.86329(15) 0.72098(14) 0.0199(5) Uani 1 1 d . . .
H25 H 0.9175 0.8977 0.7411 0.024 Uiso 1 1 calc R . .
C22 C 1.1088(2) 0.75923(15) 0.66294(14) 0.0198(5) Uani 1 1 d . . .
H22 H 1.1572 0.7244 0.6439 0.024 Uiso 1 1 calc R . .
C26A C 0.2710(2) 0.42570(14) 0.74259(14) 0.0192(5) Uani 1 1 d . . .
HF H 0.1859 0.4034 0.7599 0.023 Uiso 1 1 calc R . .
C17 C 0.6992(2) 0.54818(15) 0.95126(14) 0.0211(5) Uani 1 1 d . . .
H17 H 0.6793 0.5642 0.9951 0.025 Uiso 1 1 calc R . .
C16 C 0.7809(2) 0.60194(15) 0.87226(14) 0.0181(5) Uani 1 1 d . . .
H16 H 0.8173 0.6535 0.8636 0.022 Uiso 1 1 calc R . .
C36 C 0.9695(2) 0.90367(14) 0.49888(13) 0.0160(4) Uani 1 1 d . . .
H36 H 0.9611 0.9082 0.5493 0.019 Uiso 1 1 calc R . .
C19 C 0.6757(2) 0.44609(15) 0.90002(15) 0.0225(5) Uani 1 1 d . . .
H19 H 0.6415 0.3935 0.9099 0.027 Uiso 1 1 calc R . .
C8 C 0.8172(2) 0.57059(15) 0.48724(14) 0.0210(5) Uani 1 1 d . . .
H8A H 0.8663 0.5339 0.4682 0.032 Uiso 1 1 calc R . .
H8B H 0.8045 0.6195 0.4384 0.032 Uiso 1 1 calc R . .
H8C H 0.7359 0.5406 0.5249 0.032 Uiso 1 1 calc R . .
C16A C 0.0989(2) 0.42038(14) 0.91640(14) 0.0186(5) Uani 1 1 d . . .
HG H 0.1444 0.4601 0.8617 0.022 Uiso 1 1 calc R . .
C40 C 0.8778(2) 0.86549(14) 0.40950(14) 0.0173(4) Uani 1 1 d . . .
H40 H 0.8086 0.8441 0.4002 0.021 Uiso 1 1 calc R . .
C19A C -0.0336(2) 0.30449(15) 1.08245(14) 0.0183(5) Uani 1 1 d . . .
HH H -0.0768 0.2665 1.1385 0.022 Uiso 1 1 calc R . .
C25A C 0.3210(2) 0.49177(15) 0.66072(15) 0.0244(5) Uani 1 1 d . . .
HI H 0.2694 0.5136 0.6234 0.029 Uiso 1 1 calc R . .
C40A C 0.4905(2) 0.18217(17) 0.77810(15) 0.0222(5) Uani 1 1 d . . .
HJ H 0.4605 0.1315 0.8280 0.027 Uiso 1 1 calc R . .
C3 C 0.6071(2) 0.69706(15) 0.71776(14) 0.0178(5) Uani 1 1 d . . .
H3 H 0.6122 0.6401 0.7528 0.021 Uiso 1 1 calc R . .
C8A C 0.2759(2) 0.01587(15) 1.10794(15) 0.0240(5) Uani 1 1 d . . .
HK H 0.3185 -0.0045 1.1529 0.036 Uiso 1 1 calc R . .
HL H 0.2878 -0.0199 1.0799 0.036 Uiso 1 1 calc R . .
HM H 0.1862 0.0147 1.1320 0.036 Uiso 1 1 calc R . .
C18 C 0.6470(2) 0.47049(16) 0.96486(15) 0.0233(5) Uani 1 1 d . . .
H18 H 0.5923 0.4344 1.0180 0.028 Uiso 1 1 calc R . .
C1A C -0.0574(2) 0.34404(15) 0.76409(15) 0.0223(5) Uani 1 1 d . . .
HN H 0.0184 0.3584 0.7176 0.033 Uiso 1 1 calc R . .
HO H -0.0544 0.3792 0.7918 0.033 Uiso 1 1 calc R . .
HP H -0.1312 0.3532 0.7421 0.033 Uiso 1 1 calc R . .
C24 C 1.0972(2) 0.88306(15) 0.68674(15) 0.0228(5) Uani 1 1 d . . .
H24 H 1.1373 0.9311 0.6832 0.027 Uiso 1 1 calc R . .
C34A C 0.3089(2) 0.04313(16) 0.77331(16) 0.0261(5) Uani 1 1 d . . .
HQ H 0.3805 0.0755 0.7296 0.031 Uiso 1 1 calc R . .
C23 C 1.1686(2) 0.83126(16) 0.65800(15) 0.0241(5) Uani 1 1 d . . .
H23 H 1.2566 0.8445 0.6353 0.029 Uiso 1 1 calc R . .
C20 C 0.7553(2) 0.50018(14) 0.82045(14) 0.0189(5) Uani 1 1 d . . .
H20 H 0.7734 0.4842 0.7767 0.023 Uiso 1 1 calc R . .
C24A C 0.4476(3) 0.52511(16) 0.63461(16) 0.0293(6) Uani 1 1 d . . .
HR H 0.4807 0.5698 0.5800 0.035 Uiso 1 1 calc R . .
C36A C 0.4509(2) 0.30506(16) 0.65852(15) 0.0238(5) Uani 1 1 d . . .
HS H 0.3951 0.3364 0.6277 0.029 Uiso 1 1 calc R . .
C30 C 0.5219(2) 0.77453(16) 0.52672(15) 0.0219(5) Uani 1 1 d . . .
H30 H 0.5382 0.7209 0.5637 0.026 Uiso 1 1 calc R . .
C9 C 0.3741(2) 0.66970(19) 0.77537(18) 0.0373(7) Uani 1 1 d . . .
H9A H 0.2979 0.6906 0.7959 0.056 Uiso 1 1 calc R . .
H9B H 0.3816 0.6146 0.8190 0.056 Uiso 1 1 calc R . .
H9C H 0.3698 0.6656 0.7248 0.056 Uiso 1 1 calc R . .
C2 C 0.4910(2) 0.73095(16) 0.75364(14) 0.0241(5) Uani 1 1 d . . .
C37 C 1.0860(2) 0.92945(15) 0.43678(14) 0.0194(5) Uani 1 1 d . . .
H37 H 1.1557 0.9508 0.4457 0.023 Uiso 1 1 calc R . .
C37A C 0.5814(3) 0.33354(18) 0.62996(17) 0.0329(7) Uani 1 1 d . . .
HT H 0.6123 0.3845 0.5807 0.039 Uiso 1 1 calc R . .
C38A C 0.6642(2) 0.2861(2) 0.67484(18) 0.0354(7) Uani 1 1 d . . .
HU H 0.7510 0.3050 0.6554 0.042 Uiso 1 1 calc R . .
C10 C 1.0183(2) 0.64762(16) 0.47441(15) 0.0231(5) Uani 1 1 d . . .
H10A H 1.0661 0.6618 0.5056 0.035 Uiso 1 1 calc R . .
H10B H 1.0046 0.6988 0.4282 0.035 Uiso 1 1 calc R . .
H10C H 1.0652 0.6128 0.4516 0.035 Uiso 1 1 calc R . .
C34 C 0.5668(3) 0.92685(17) 0.45793(15) 0.0269(5) Uani 1 1 d . . .
H34 H 0.6137 0.9755 0.4483 0.032 Uiso 1 1 calc R . .
C9A C -0.1920(2) 0.22393(18) 0.89833(15) 0.0257(5) Uani 1 1 d . . .
HV H -0.2615 0.2331 0.8722 0.039 Uiso 1 1 calc R . .
HW H -0.1975 0.2570 0.9290 0.039 Uiso 1 1 calc R . .
HX H -0.1967 0.1648 0.9375 0.039 Uiso 1 1 calc R . .
C31A C 0.0938(2) -0.05383(15) 0.90151(15) 0.0230(5) Uani 1 1 d . . .
HY H 0.0213 -0.0864 0.9442 0.028 Uiso 1 1 calc R . .
C23A C 0.5252(2) 0.49193(17) 0.68986(16) 0.0296(6) Uani 1 1 d . . .
HZ H 0.6105 0.5139 0.6719 0.036 Uiso 1 1 calc R . .
C17A C -0.0164(2) 0.43763(16) 0.95656(15) 0.0241(5) Uani 1 1 d . . .
H0AA H -0.0496 0.4880 0.9277 0.029 Uiso 1 1 calc R . .
C39A C 0.6193(2) 0.21067(19) 0.74831(17) 0.0301(6) Uani 1 1 d . . .
H1AA H 0.6759 0.1788 0.7780 0.036 Uiso 1 1 calc R . .
C10A C 0.4764(2) 0.11102(17) 1.00575(15) 0.0243(5) Uani 1 1 d . . .
H2AA H 0.5107 0.1691 0.9680 0.036 Uiso 1 1 calc R . .
H3AA H 0.4920 0.0785 0.9743 0.036 Uiso 1 1 calc R . .
H4AA H 0.5168 0.0882 1.0518 0.036 Uiso 1 1 calc R . .
C22A C 0.4760(2) 0.42634(16) 0.77136(15) 0.0226(5) Uani 1 1 d . . .
H5AA H 0.5285 0.4044 0.8081 0.027 Uiso 1 1 calc R . .
C33A C 0.2934(3) -0.04426(17) 0.80255(18) 0.0338(6) Uani 1 1 d . . .
H6AA H 0.3550 -0.0703 0.7791 0.041 Uiso 1 1 calc R . .
C18A C -0.0823(2) 0.38037(16) 1.03914(15) 0.0232(5) Uani 1 1 d . . .
H7AA H -0.1593 0.3925 1.0658 0.028 Uiso 1 1 calc R . .
C32A C 0.1857(2) -0.09233(16) 0.86673(17) 0.0284(6) Uani 1 1 d . . .
H8AA H 0.1753 -0.1508 0.8865 0.034 Uiso 1 1 calc R . .
C32 C 0.4025(3) 0.8617(2) 0.43076(18) 0.0394(8) Uani 1 1 d . . .
H32 H 0.3394 0.8668 0.4025 0.047 Uiso 1 1 calc R . .
C1 C 0.5075(3) 0.7346(2) 0.83377(16) 0.0364(7) Uani 1 1 d . . .
H1A H 0.5713 0.7802 0.8171 0.055 Uiso 1 1 calc R . .
H1B H 0.5337 0.6818 0.8702 0.055 Uiso 1 1 calc R . .
H1C H 0.4277 0.7439 0.8643 0.055 Uiso 1 1 calc R . .
C33 C 0.4711(3) 0.9337(2) 0.41770(17) 0.0399(7) Uani 1 1 d . . .
H33 H 0.4528 0.9871 0.3817 0.048 Uiso 1 1 calc R . .
C31 C 0.4269(2) 0.7823(2) 0.48533(17) 0.0319(6) Uani 1 1 d . . .
H31 H 0.3798 0.7340 0.4944 0.038 Uiso 1 1 calc R . .
O41 O 0.6354(3) 0.94186(19) 0.74688(17) 0.0660(7) Uani 1 1 d G . .
H41A H 0.6564 0.9105 0.7927 0.099 Uiso 1 1 d G . .
H41B H 0.6717 0.9285 0.7076 0.099 Uiso 1 1 d G . .


_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
P27 O28 1.4978(15) . ?
P27 C4 1.825(2) . ?
P27 C29 1.803(2) . ?
P27 C35 1.798(2) . ?
P27A O28A 1.4924(16) . ?
P27A C4A 1.824(2) . ?
P27A C29A 1.809(2) . ?
P27A C35A 1.809(2) . ?
P13A O14A 1.4961(15) . ?
P13A C5A 1.827(2) . ?
P13A C15A 1.810(2) . ?
P13A C21A 1.811(2) . ?
P13 O14 1.4939(16) . ?
P13 C15 1.804(2) . ?
P13 C21 1.808(2) . ?
P13 C5 1.825(2) . ?
O12A C7A 1.428(2) . ?
O11A C2A 1.429(2) . ?
O12 C7 1.429(3) . ?
O11 C2 1.421(3) . ?
C6 C7 1.527(3) . ?
C6 C5 1.343(3) . ?
C5A C4A 1.513(3) . ?
C5A C6A 1.338(3) . ?
C4 C5 1.508(3) . ?
C4 C3 1.346(3) . ?
C15 C16 1.399(3) . ?
C15 C20 1.407(3) . ?
C21 C26 1.397(3) . ?
C21 C22 1.401(3) . ?
C4A C3A 1.343(3) . ?
C29 C30 1.395(3) . ?
C29 C34 1.397(3) . ?
C7 C8 1.524(3) . ?
C7 C10 1.536(3) . ?
C6A C7A 1.528(3) . ?
C15A C20A 1.399(3) . ?
C15A C16A 1.394(3) . ?
C2A C3A 1.523(3) . ?
C2A C1A 1.525(3) . ?
C2A C9A 1.526(3) . ?
C20A C19A 1.385(3) . ?
C29A C30A 1.398(3) . ?
C29A C34A 1.392(3) . ?
C30A C31A 1.390(3) . ?
C35A C40A 1.398(3) . ?
C35A C36A 1.392(3) . ?
C21A C26A 1.398(3) . ?
C21A C22A 1.399(3) . ?
C35 C36 1.400(3) . ?
C35 C40 1.396(3) . ?
C26 C25 1.387(3) . ?
C38 C39 1.387(3) . ?
C38 C37 1.387(3) . ?
C7A C8A 1.523(3) . ?
C7A C10A 1.538(3) . ?
C39 C40 1.387(3) . ?
C25 C24 1.394(3) . ?
C22 C23 1.395(3) . ?
C26A C25A 1.389(3) . ?
C17 C16 1.385(3) . ?
C17 C18 1.387(3) . ?
C36 C37 1.389(3) . ?
C19 C18 1.385(3) . ?
C19 C20 1.384(3) . ?
C16A C17A 1.388(3) . ?
C19A C18A 1.393(3) . ?
C25A C24A 1.385(3) . ?
C40A C39A 1.381(3) . ?
C3 C2 1.513(3) . ?
C24 C23 1.383(4) . ?
C34A C33A 1.390(4) . ?
C24A C23A 1.388(4) . ?
C36A C37A 1.400(3) . ?
C30 C31 1.388(3) . ?
C9 C2 1.535(4) . ?
C2 C1 1.529(4) . ?
C37A C38A 1.379(4) . ?
C38A C39A 1.378(4) . ?
C34 C33 1.383(4) . ?
C31A C32A 1.381(3) . ?
C23A C22A 1.381(3) . ?
C17A C18A 1.382(3) . ?
C33A C32A 1.385(4) . ?
C32 C33 1.382(5) . ?
C32 C31 1.377(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
O28 P27 C4 111.64(9) . . ?
O28 P27 C29 113.14(10) . . ?
O28 P27 C35 110.85(9) . . ?
C29 P27 C4 105.63(10) . . ?
C35 P27 C4 109.46(10) . . ?
C35 P27 C29 105.83(10) . . ?
O28A P27A C4A 112.38(9) . . ?
O28A P27A C29A 113.28(9) . . ?
O28A P27A C35A 110.66(10) . . ?
C29A P27A C4A 105.97(9) . . ?
C29A P27A C35A 106.22(10) . . ?
C35A P27A C4A 107.95(9) . . ?
O14A P13A C5A 113.32(9) . . ?
O14A P13A C15A 112.62(9) . . ?
O14A P13A C21A 110.22(9) . . ?
C15A P13A C5A 103.45(9) . . ?
C15A P13A C21A 107.46(10) . . ?
C21A P13A C5A 109.43(9) . . ?
O14 P13 C15 111.25(10) . . ?
O14 P13 C21 110.76(10) . . ?
O14 P13 C5 114.12(9) . . ?
C15 P13 C21 108.57(10) . . ?
C15 P13 C5 104.90(9) . . ?
C21 P13 C5 106.91(10) . . ?
C5 C6 C7 133.0(2) . . ?
C4A C5A P13A 115.45(15) . . ?
C6A C5A P13A 124.66(16) . . ?
C6A C5A C4A 119.78(18) . . ?
C5 C4 P27 119.41(14) . . ?
C3 C4 P27 121.25(17) . . ?
C3 C4 C5 119.3(2) . . ?
C16 C15 P13 124.85(17) . . ?
C16 C15 C20 118.8(2) . . ?
C20 C15 P13 116.32(16) . . ?
C26 C21 P13 125.53(16) . . ?
C26 C21 C22 119.0(2) . . ?
C22 C21 P13 115.46(17) . . ?
C5A C4A P27A 117.32(14) . . ?
C3A C4A P27A 124.19(16) . . ?
C3A C4A C5A 118.48(17) . . ?
C30 C29 P27 123.23(18) . . ?
C30 C29 C34 119.2(2) . . ?
C34 C29 P27 117.57(18) . . ?
O12 C7 C6 112.25(17) . . ?
O12 C7 C8 105.59(17) . . ?
O12 C7 C10 110.96(19) . . ?
C6 C7 C10 109.67(18) . . ?
C8 C7 C6 108.85(18) . . ?
C8 C7 C10 109.40(18) . . ?
C5A C6A C7A 133.47(19) . . ?
C6 C5 P13 125.21(17) . . ?
C6 C5 C4 118.84(19) . . ?
C4 C5 P13 115.96(14) . . ?
C20A C15A P13A 117.18(17) . . ?
C16A C15A P13A 123.53(17) . . ?
C16A C15A C20A 119.3(2) . . ?
O11A C2A C3A 113.47(18) . . ?
O11A C2A C1A 110.21(17) . . ?
O11A C2A C9A 105.37(17) . . ?
C3A C2A C1A 109.18(17) . . ?
C3A C2A C9A 108.08(17) . . ?
C1A C2A C9A 110.5(2) . . ?
C19A C20A C15A 120.5(2) . . ?
C4A C3A C2A 134.06(19) . . ?
C30A C29A P27A 120.84(17) . . ?
C34A C29A P27A 119.88(17) . . ?
C34A C29A C30A 119.1(2) . . ?
C31A C30A C29A 120.1(2) . . ?
C40A C35A P27A 123.57(17) . . ?
C36A C35A P27A 116.79(18) . . ?
C36A C35A C40A 119.6(2) . . ?
C26A C21A P13A 125.28(16) . . ?
C26A C21A C22A 118.9(2) . . ?
C22A C21A P13A 115.62(17) . . ?
C36 C35 P27 118.04(15) . . ?
C40 C35 P27 122.49(16) . . ?
C40 C35 C36 119.39(19) . . ?
C25 C26 C21 120.6(2) . . ?
C37 C38 C39 120.4(2) . . ?
O12A C7A C6A 112.73(18) . . ?
O12A C7A C8A 105.45(17) . . ?
O12A C7A C10A 109.80(18) . . ?
C6A C7A C10A 109.74(17) . . ?
C8A C7A C6A 108.37(17) . . ?
C8A C7A C10A 110.67(19) . . ?
C38 C39 C40 120.1(2) . . ?
C26 C25 C24 120.0(2) . . ?
C23 C22 C21 120.2(2) . . ?
C25A C26A C21A 120.2(2) . . ?
C16 C17 C18 119.9(2) . . ?
C17 C16 C15 120.5(2) . . ?
C37 C36 C35 120.19(19) . . ?
C20 C19 C18 119.9(2) . . ?
C17A C16A C15A 120.0(2) . . ?
C39 C40 C35 120.1(2) . . ?
C20A C19A C18A 119.7(2) . . ?
C24A C25A C26A 120.1(2) . . ?
C39A C40A C35A 120.0(2) . . ?
C4 C3 C2 133.7(2) . . ?
C19 C18 C17 120.6(2) . . ?
C23 C24 C25 120.1(2) . . ?
C33A C34A C29A 120.6(2) . . ?
C24 C23 C22 120.2(2) . . ?
C19 C20 C15 120.4(2) . . ?
C25A C24A C23A 120.1(2) . . ?
C35A C36A C37A 119.5(3) . . ?
C31 C30 C29 120.3(2) . . ?
O11 C2 C3 115.37(18) . . ?
O11 C2 C9 104.8(2) . . ?
O11 C2 C1 109.7(2) . . ?
C3 C2 C9 107.1(2) . . ?
C3 C2 C1 108.53(19) . . ?
C1 C2 C9 111.3(2) . . ?
C38 C37 C36 119.8(2) . . ?
C38A C37A C36A 120.1(3) . . ?
C39A C38A C37A 120.4(2) . . ?
C33 C34 C29 119.9(3) . . ?
C32A C31A C30A 120.2(2) . . ?
C22A C23A C24A 120.1(2) . . ?
C18A C17A C16A 120.4(2) . . ?
C38A C39A C40A 120.3(3) . . ?
C23A C22A C21A 120.5(2) . . ?
C32A C33A C34A 119.7(2) . . ?
C17A C18A C19A 120.1(2) . . ?
C31A C32A C33A 120.3(2) . . ?
C31 C32 C33 120.4(2) . . ?
C32 C33 C34 120.3(3) . . ?
C32 C31 C30 119.9(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P27 C4 C5 P13 111.76(15) . . . . ?
P27 C4 C5 C6 -68.1(2) . . . . ?
P27 C4 C3 C2 -0.4(4) . . . . ?
P27 C29 C30 C31 178.01(17) . . . . ?
P27 C29 C34 C33 -177.55(19) . . . . ?
P27 C35 C36 C37 -177.59(18) . . . . ?
P27 C35 C40 C39 176.89(18) . . . . ?
P27A C4A C3A C2A -0.5(3) . . . . ?
P27A C29A C30A C31A 175.99(17) . . . . ?
P27A C29A C34A C33A -176.4(2) . . . . ?
P27A C35A C40A C39A 178.85(17) . . . . ?
P27A C35A C36A C37A -179.85(17) . . . . ?
P13A C5A C4A P27A 110.58(14) . . . . ?
P13A C5A C4A C3A -70.4(2) . . . . ?
P13A C5A C6A C7A 1.3(3) . . . . ?
P13A C15A C20A C19A 179.99(16) . . . . ?
P13A C15A C16A C17A 178.07(17) . . . . ?
P13A C21A C26A C25A 174.33(17) . . . . ?
P13A C21A C22A C23A -174.88(19) . . . . ?
P13 C15 C16 C17 178.86(17) . . . . ?
P13 C15 C20 C19 179.93(18) . . . . ?
P13 C21 C26 C25 179.09(16) . . . . ?
P13 C21 C22 C23 -179.90(17) . . . . ?
O28A P27A C4A C5A -153.95(14) . . . . ?
O28A P27A C4A C3A 27.1(2) . . . . ?
O28A P27A C29A C30A -87.94(19) . . . . ?
O28A P27A C29A C34A 86.6(2) . . . . ?
O28A P27A C35A C40A -159.38(17) . . . . ?
O28A P27A C35A C36A 19.16(19) . . . . ?
O14A P13A C5A C4A -167.29(13) . . . . ?
O14A P13A C5A C6A 16.6(2) . . . . ?
O14A P13A C15A C20A -65.39(17) . . . . ?
O14A P13A C15A C16A 113.95(18) . . . . ?
O14A P13A C21A C26A -168.22(18) . . . . ?
O14A P13A C21A C22A 7.0(2) . . . . ?
O28 P27 C4 C5 -131.63(15) . . . . ?
O28 P27 C4 C3 50.4(2) . . . . ?
O28 P27 C29 C30 -129.45(18) . . . . ?
O28 P27 C29 C34 48.1(2) . . . . ?
O28 P27 C35 C36 33.5(2) . . . . ?
O28 P27 C35 C40 -143.19(18) . . . . ?
O11A C2A C3A C4A 31.6(3) . . . . ?
O14 P13 C15 C16 124.94(19) . . . . ?
O14 P13 C15 C20 -54.82(19) . . . . ?
O14 P13 C21 C26 -171.88(18) . . . . ?
O14 P13 C21 C22 7.8(2) . . . . ?
O14 P13 C5 C6 5.2(2) . . . . ?
O14 P13 C5 C4 -174.68(14) . . . . ?
C5A P13A C15A C20A 57.33(17) . . . . ?
C5A P13A C15A C16A -123.33(18) . . . . ?
C5A P13A C21A C26A 66.5(2) . . . . ?
C5A P13A C21A C22A -118.25(18) . . . . ?
C5A C4A C3A C2A -179.5(2) . . . . ?
C5A C6A C7A O12A 37.2(3) . . . . ?
C5A C6A C7A C8A 153.6(2) . . . . ?
C5A C6A C7A C10A -85.5(3) . . . . ?
C4 P27 C29 C30 -7.0(2) . . . . ?
C4 P27 C29 C34 170.49(17) . . . . ?
C4 P27 C35 C36 -90.12(19) . . . . ?
C4 P27 C35 C40 93.2(2) . . . . ?
C4 C3 C2 O11 12.0(4) . . . . ?
C4 C3 C2 C9 128.3(3) . . . . ?
C4 C3 C2 C1 -111.4(3) . . . . ?
C15 P13 C21 C26 -49.5(2) . . . . ?
C15 P13 C21 C22 130.20(17) . . . . ?
C15 P13 C5 C6 -116.83(19) . . . . ?
C15 P13 C5 C4 63.31(17) . . . . ?
C21 P13 C15 C16 2.8(2) . . . . ?
C21 P13 C15 C20 -176.95(17) . . . . ?
C21 P13 C5 C6 128.00(19) . . . . ?
C21 P13 C5 C4 -51.86(17) . . . . ?
C21 C26 C25 C24 1.1(3) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C4A P27A C29A C30A 35.7(2) . . . . ?
C4A P27A C29A C34A -149.77(18) . . . . ?
C4A P27A C35A C40A 77.3(2) . . . . ?
C4A P27A C35A C36A -104.20(17) . . . . ?
C4A C5A C6A C7A -174.6(2) . . . . ?
C29 P27 C4 C5 105.01(16) . . . . ?
C29 P27 C4 C3 -72.99(19) . . . . ?
C29 P27 C35 C36 156.49(18) . . . . ?
C29 P27 C35 C40 -20.2(2) . . . . ?
C29 C30 C31 C32 -0.2(4) . . . . ?
C29 C34 C33 C32 -1.0(4) . . . . ?
C7 C6 C5 P13 5.3(3) . . . . ?
C7 C6 C5 C4 -174.9(2) . . . . ?
C6A C5A C4A P27A -73.1(2) . . . . ?
C6A C5A C4A C3A 105.9(2) . . . . ?
C5 P13 C15 C16 -111.2(2) . . . . ?
C5 P13 C15 C20 69.04(19) . . . . ?
C5 P13 C21 C26 63.2(2) . . . . ?
C5 P13 C21 C22 -117.12(17) . . . . ?
C5 C6 C7 O12 39.6(3) . . . . ?
C5 C6 C7 C8 156.1(2) . . . . ?
C5 C6 C7 C10 -84.3(3) . . . . ?
C5 C4 C3 C2 -178.4(2) . . . . ?
C15A P13A C5A C4A 70.46(16) . . . . ?
C15A P13A C5A C6A -105.63(19) . . . . ?
C15A P13A C21A C26A -45.2(2) . . . . ?
C15A P13A C21A C22A 130.07(17) . . . . ?
C15A C20A C19A C18A 1.4(3) . . . . ?
C15A C16A C17A C18A 2.5(3) . . . . ?
C20A C15A C16A C17A -2.6(3) . . . . ?
C20A C19A C18A C17A -1.5(3) . . . . ?
C29A P27A C4A C5A 81.83(16) . . . . ?
C29A P27A C4A C3A -97.15(19) . . . . ?
C29A P27A C35A C40A -36.0(2) . . . . ?
C29A P27A C35A C36A 142.51(16) . . . . ?
C29A C30A C31A C32A -0.3(4) . . . . ?
C29A C34A C33A C32A 1.0(4) . . . . ?
C30A C29A C34A C33A -1.8(4) . . . . ?
C30A C31A C32A C33A -0.6(4) . . . . ?
C35A P27A C4A C5A -31.64(18) . . . . ?
C35A P27A C4A C3A 149.39(18) . . . . ?
C35A P27A C29A C30A 150.38(17) . . . . ?
C35A P27A C29A C34A -35.1(2) . . . . ?
C35A C40A C39A C38A 0.5(3) . . . . ?
C35A C36A C37A C38A 1.3(3) . . . . ?
C21A P13A C5A C4A -43.84(17) . . . . ?
C21A P13A C5A C6A 140.06(18) . . . . ?
C21A P13A C15A C20A 173.04(15) . . . . ?
C21A P13A C15A C16A -7.6(2) . . . . ?
C21A C26A C25A C24A 0.1(3) . . . . ?
C35 P27 C4 C5 -8.52(18) . . . . ?
C35 P27 C4 C3 173.49(17) . . . . ?
C35 P27 C29 C30 108.99(19) . . . . ?
C35 P27 C29 C34 -73.48(19) . . . . ?
C35 C36 C37 C38 0.5(3) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
C26 C25 C24 C23 -1.0(3) . . . . ?
C38 C39 C40 C35 0.6(3) . . . . ?
C39 C38 C37 C36 0.4(4) . . . . ?
C25 C24 C23 C22 0.2(3) . . . . ?
C22 C21 C26 C25 -0.5(3) . . . . ?
C26A C21A C22A C23A 0.7(3) . . . . ?
C26A C25A C24A C23A 0.7(4) . . . . ?
C16 C15 C20 C19 0.2(3) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C36 C35 C40 C39 0.3(3) . . . . ?
C16A C15A C20A C19A 0.6(3) . . . . ?
C16A C17A C18A C19A -0.4(4) . . . . ?
C40 C35 C36 C37 -0.8(3) . . . . ?
C25A C24A C23A C22A -0.8(4) . . . . ?
C40A C35A C36A C37A -1.3(3) . . . . ?
C3 C4 C5 P13 -70.2(2) . . . . ?
C3 C4 C5 C6 109.9(2) . . . . ?
C18 C17 C16 C15 1.4(4) . . . . ?
C18 C19 C20 C15 1.1(4) . . . . ?
C1A C2A C3A C4A -91.7(3) . . . . ?
C34A C29A C30A C31A 1.4(3) . . . . ?
C34A C33A C32A C31A 0.2(4) . . . . ?
C20 C15 C16 C17 -1.4(3) . . . . ?
C20 C19 C18 C17 -1.1(4) . . . . ?
C24A C23A C22A C21A 0.1(4) . . . . ?
C36A C35A C40A C39A 0.4(3) . . . . ?
C36A C37A C38A C39A -0.4(4) . . . . ?
C30 C29 C34 C33 0.1(3) . . . . ?
C37 C38 C39 C40 -1.0(4) . . . . ?
C37A C38A C39A C40A -0.5(4) . . . . ?
C34 C29 C30 C31 0.5(3) . . . . ?
C9A C2A C3A C4A 148.1(2) . . . . ?
C22A C21A C26A C25A -0.8(3) . . . . ?
C33 C32 C31 C30 -0.7(4) . . . . ?
C31 C32 C33 C34 1.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1026532'
