# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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.
#
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#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_global
_audit_creation_date             2013-06-27
_audit_creation_method           SHELXL-97


_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 P, C7 H5 O3'
_chemical_formula_sum            'C23 H41 O3 P'
_chemical_formula_weight         396.53

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z

_cell_length_a                   9.9732(2)
_cell_length_b                   15.1013(3)
_cell_length_c                   16.2700(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.6620(10)
_cell_angle_gamma                90.00
_cell_volume                     2390.80(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    35350
_cell_measurement_theta_min      4.04
_cell_measurement_theta_max      68.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.450
_exptl_absorpt_correction_T_max  0.562
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            43847
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0070
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.04
_diffrn_reflns_theta_max         68.25
_reflns_number_total             4363
_reflns_number_gt                3937
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID AUTO (Rigaku, 2004)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1017P)^2^+0.8453P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4363
_refine_ls_number_parameters     257
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1982
_refine_ls_wR_factor_gt          0.1952
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.206
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.25571(6) 0.42439(5) 0.37687(3) 0.0578(2) Uani 1 1 d . . .
O1 O 0.1443(2) 0.17511(14) 0.21634(15) 0.0851(6) Uani 1 1 d . . .
O2 O 0.2668(3) 0.12643(18) 0.10873(13) 0.0910(7) Uani 1 1 d . . .
O3 O 0.3503(2) -0.0098(2) 0.10821(14) 0.0998(8) Uani 1 1 d . . .
C1 C 0.1653(3) 0.09429(19) 0.25075(16) 0.0637(6) Uani 1 1 d . . .
C2 C 0.2353(2) 0.02848(18) 0.21600(14) 0.0585(6) Uani 1 1 d . . .
C3 C 0.2532(3) -0.0532(2) 0.25427(19) 0.0783(8) Uani 1 1 d . . .
H3 H 0.3002 -0.0981 0.2309 0.094 Uiso 1 1 calc R . .
C4 C 0.2051(4) -0.0718(2) 0.3255(2) 0.0911(10) Uani 1 1 d . . .
H4 H 0.2202 -0.1283 0.3516 0.109 Uiso 1 1 calc R . .
C5 C 0.1345(3) -0.0067(3) 0.35828(19) 0.0895(10) Uani 1 1 d . . .
H5 H 0.0993 -0.0191 0.4068 0.107 Uiso 1 1 calc R . .
C6 C 0.1148(3) 0.0751(2) 0.32189(18) 0.0775(8) Uani 1 1 d . . .
H6 H 0.0662 0.1191 0.3453 0.093 Uiso 1 1 calc R . .
C7 C 0.2899(3) 0.0480(2) 0.13851(17) 0.0729(8) Uani 1 1 d . . .
C8 C 0.0999(3) 0.4111(2) 0.41392(17) 0.0691(7) Uani 1 1 d . . .
H8A H 0.1159 0.4335 0.4725 0.083 Uiso 1 1 calc R . .
H8B H 0.0279 0.4487 0.3790 0.083 Uiso 1 1 calc R . .
C9 C 0.0458(3) 0.3175(2) 0.4125(2) 0.0845(9) Uani 1 1 d . . .
H9A H 0.1217 0.2778 0.4395 0.101 Uiso 1 1 calc R . .
H9B H 0.0141 0.2984 0.3532 0.101 Uiso 1 1 calc R . .
C10 C -0.0715(3) 0.3077(3) 0.4572(2) 0.0976(11) Uani 1 1 d . . .
H10A H -0.0422 0.3307 0.5153 0.117 Uiso 1 1 calc R . .
H10B H -0.1502 0.3438 0.4276 0.117 Uiso 1 1 calc R . .
C11 C -0.1172(4) 0.2128(3) 0.4606(3) 0.1224(15) Uani 1 1 d . . .
H11A H -0.1498 0.1904 0.4031 0.147 Uiso 1 1 calc R . .
H11B H -0.1918 0.2097 0.4909 0.147 Uiso 1 1 calc R . .
H11C H -0.0397 0.1767 0.4899 0.147 Uiso 1 1 calc R . .
C12 C 0.3918(2) 0.35592(18) 0.43381(14) 0.0585(6) Uani 1 1 d . . .
H12A H 0.4805 0.3819 0.4283 0.070 Uiso 1 1 calc R . .
H12B H 0.3891 0.3578 0.4942 0.070 Uiso 1 1 calc R . .
C13 C 0.3887(3) 0.2588(2) 0.40629(18) 0.0721(7) Uani 1 1 d . . .
H13A H 0.3010 0.2318 0.4123 0.086 Uiso 1 1 calc R . .
H13B H 0.3924 0.2561 0.3460 0.086 Uiso 1 1 calc R . .
C14 C 0.5048(3) 0.2068(2) 0.4563(2) 0.0817(8) Uani 1 1 d . . .
H14A H 0.5003 0.2097 0.5165 0.098 Uiso 1 1 calc R . .
H14B H 0.5921 0.2348 0.4508 0.098 Uiso 1 1 calc R . .
C15 C 0.5067(4) 0.1108(2) 0.4308(2) 0.0907(9) Uani 1 1 d . . .
H15A H 0.5226 0.1069 0.3736 0.109 Uiso 1 1 calc R . .
H15B H 0.4182 0.0833 0.4323 0.109 Uiso 1 1 calc R . .
H15C H 0.5805 0.0797 0.4699 0.109 Uiso 1 1 calc R . .
C16 C 0.2249(3) 0.3972(2) 0.26660(14) 0.0644(6) Uani 1 1 d . . .
H16A H 0.2004 0.3337 0.2591 0.077 Uiso 1 1 calc R . .
H16B H 0.1458 0.4322 0.2357 0.077 Uiso 1 1 calc R . .
C17 C 0.3505(3) 0.4157(2) 0.22877(16) 0.0696(7) Uani 1 1 d . . .
H17A H 0.3660 0.4805 0.2289 0.084 Uiso 1 1 calc R . .
H17B H 0.4324 0.3884 0.2655 0.084 Uiso 1 1 calc R . .
C18 C 0.3377(4) 0.3818(3) 0.14072(19) 0.0917(10) Uani 1 1 d D . .
H18A H 0.4212 0.3991 0.1211 0.110 Uiso 1 1 calc R . .
H18B H 0.3350 0.3163 0.1421 0.110 Uiso 1 1 calc R . .
C19 C 0.2188(4) 0.4128(4) 0.0800(2) 0.150(2) Uani 1 1 d D . .
H19A H 0.1363 0.3830 0.0897 0.180 Uiso 1 1 calc R . .
H19B H 0.2301 0.3995 0.0230 0.180 Uiso 1 1 calc R . .
H19C H 0.2092 0.4769 0.0861 0.180 Uiso 1 1 calc R . .
C20 C 0.3101(3) 0.53732(19) 0.39375(17) 0.0711(7) Uani 1 1 d D B .
H20A H 0.3235 0.5516 0.4544 0.085 Uiso 1 1 calc R . .
H20B H 0.3995 0.5450 0.3775 0.085 Uiso 1 1 calc R . .
C21 C 0.2055(4) 0.6010(2) 0.3428(3) 0.1112(13) Uani 1 1 d DU . .
H21A H 0.1717 0.5755 0.2860 0.133 Uiso 0.63 1 calc PR A 1
H21B H 0.1261 0.6049 0.3700 0.133 Uiso 0.63 1 calc PR A 1
H21C H 0.1766 0.6424 0.3829 0.133 Uiso 0.37 1 d PR A 2
H21D H 0.1228 0.5673 0.3150 0.133 Uiso 0.37 1 d PR A 2
C22A C 0.2553(5) 0.6917(3) 0.3331(4) 0.0888(15) Uani 0.63 1 d PDU B 1
H22A H 0.2815 0.7191 0.3896 0.107 Uiso 0.63 1 calc PR B 1
H22B H 0.1783 0.7267 0.2998 0.107 Uiso 0.63 1 calc PR B 1
C22B C 0.2441(6) 0.6528(5) 0.2746(4) 0.0772(19) Uani 0.37 1 d PDU B 2
H22C H 0.1719 0.6980 0.2563 0.093 Uiso 0.37 1 calc PR B 2
H22D H 0.2406 0.6122 0.2264 0.093 Uiso 0.37 1 calc PR B 2
C23 C 0.3791(4) 0.6991(2) 0.2901(3) 0.1085(12) Uani 1 1 d DU . .
H23A H 0.4060 0.7614 0.2883 0.130 Uiso 0.63 1 calc PR B 1
H23B H 0.3530 0.6758 0.2326 0.130 Uiso 0.63 1 calc PR B 1
H23C H 0.4566 0.6649 0.3222 0.130 Uiso 0.63 1 calc PR B 1
H23D H 0.3821 0.7310 0.2380 0.130 Uiso 0.37 1 d PR B 2
H23E H 0.3908 0.7412 0.3370 0.130 Uiso 0.37 1 d PR B 2
H23F H 0.4533 0.6553 0.3016 0.130 Uiso 0.37 1 d PR B 2
H1 H 0.193(3) 0.167(2) 0.171(2) 0.088(10) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0522(4) 0.0788(5) 0.0418(3) -0.0024(2) 0.0087(3) 0.0086(3)
O1 0.0958(15) 0.0804(14) 0.0776(13) -0.0024(11) 0.0159(12) 0.0005(11)
O2 0.1038(17) 0.1153(18) 0.0551(11) 0.0075(11) 0.0200(11) -0.0241(13)
O3 0.0886(15) 0.149(2) 0.0695(13) -0.0150(13) 0.0334(11) 0.0113(15)
C1 0.0527(13) 0.0813(17) 0.0543(13) -0.0077(12) 0.0058(10) -0.0117(11)
C2 0.0466(12) 0.0822(16) 0.0450(11) -0.0040(11) 0.0061(9) -0.0078(11)
C3 0.0808(19) 0.0869(19) 0.0659(16) -0.0025(14) 0.0134(14) 0.0040(15)
C4 0.109(3) 0.098(2) 0.0663(18) 0.0147(16) 0.0188(18) -0.0150(19)
C5 0.089(2) 0.128(3) 0.0570(16) -0.0018(18) 0.0280(15) -0.035(2)
C6 0.0647(16) 0.110(2) 0.0615(16) -0.0199(15) 0.0224(13) -0.0108(15)
C7 0.0559(14) 0.112(2) 0.0490(13) -0.0078(15) 0.0083(11) -0.0119(15)
C8 0.0531(14) 0.101(2) 0.0543(14) -0.0040(13) 0.0137(11) 0.0127(13)
C9 0.0667(17) 0.112(2) 0.0820(19) -0.0029(17) 0.0315(15) 0.0027(16)
C10 0.0637(18) 0.139(3) 0.098(2) 0.006(2) 0.0362(17) 0.0054(19)
C11 0.079(2) 0.163(4) 0.138(4) 0.026(3) 0.053(2) 0.004(2)
C12 0.0513(12) 0.0777(15) 0.0457(11) 0.0017(10) 0.0088(9) 0.0068(11)
C13 0.0609(15) 0.0822(18) 0.0693(16) 0.0003(13) 0.0062(12) 0.0050(13)
C14 0.0680(17) 0.088(2) 0.0836(19) 0.0095(15) 0.0035(14) 0.0071(14)
C15 0.079(2) 0.081(2) 0.109(3) 0.0131(18) 0.0137(18) 0.0120(16)
C16 0.0617(14) 0.0885(17) 0.0408(11) -0.0035(11) 0.0063(10) 0.0066(12)
C17 0.0709(16) 0.0905(19) 0.0486(13) -0.0006(12) 0.0158(12) 0.0068(13)
C18 0.093(2) 0.123(3) 0.0635(17) -0.0147(17) 0.0286(16) -0.006(2)
C19 0.097(3) 0.294(8) 0.0553(19) -0.018(3) 0.0124(19) 0.016(4)
C20 0.0691(16) 0.0793(17) 0.0658(15) 0.0000(13) 0.0168(13) 0.0116(13)
C21 0.088(2) 0.109(3) 0.140(4) 0.040(3) 0.034(2) 0.035(2)
C22A 0.079(3) 0.067(3) 0.106(4) -0.016(3) -0.011(3) 0.012(2)
C22B 0.078(5) 0.068(4) 0.082(5) -0.001(4) 0.010(4) 0.013(3)
C23 0.098(2) 0.083(2) 0.135(3) 0.028(2) 0.007(2) -0.0006(18)

_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 C20 1.793(3) . ?
P1 C12 1.794(2) . ?
P1 C8 1.797(3) . ?
P1 C16 1.800(2) . ?
O1 C1 1.340(3) . ?
O1 H1 0.98(4) . ?
O2 C7 1.282(4) . ?
O3 C7 1.224(4) . ?
C1 C6 1.391(4) . ?
C1 C2 1.403(4) . ?
C2 C3 1.375(4) . ?
C2 C7 1.507(4) . ?
C3 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.365(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.511(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.513(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.508(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.531(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.485(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.511(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.537(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.500(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.445(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.524(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22A 1.477(4) . ?
C21 C22B 1.476(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C22A C23 1.551(4) . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
C22B C23 1.489(5) . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 H23D 0.9800 . ?
C23 H23E 0.9800 . ?
C23 H23F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 P1 C12 107.45(12) . . ?
C20 P1 C8 108.06(13) . . ?
C12 P1 C8 111.99(12) . . ?
C20 P1 C16 110.47(14) . . ?
C12 P1 C16 109.12(12) . . ?
C8 P1 C16 109.73(13) . . ?
C1 O1 H1 99(2) . . ?
O1 C1 C6 119.1(3) . . ?
O1 C1 C2 121.5(2) . . ?
C6 C1 C2 119.4(3) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 C7 121.3(3) . . ?
C1 C2 C7 120.1(3) . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O3 C7 O2 124.8(3) . . ?
O3 C7 C2 119.8(3) . . ?
O2 C7 C2 115.4(3) . . ?
C9 C8 P1 115.59(19) . . ?
C9 C8 H8A 108.4 . . ?
P1 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
P1 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C8 C9 C10 113.3(3) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 112.5(3) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 P1 115.88(17) . . ?
C13 C12 H12A 108.3 . . ?
P1 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
P1 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C12 112.5(2) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 114.3(3) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 P1 112.42(18) . . ?
C17 C16 H16A 109.1 . . ?
P1 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
P1 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 114.5(3) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 115.3(3) . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C17 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 P1 111.6(2) . . ?
C21 C20 H20A 109.3 . . ?
P1 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
P1 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C22A C21 C20 115.9(3) . . ?
C22B C21 C20 118.8(4) . . ?
C22A C21 H21A 108.3 . . ?
C20 C21 H21A 108.3 . . ?
C22A C21 H21B 108.3 . . ?
C22B C21 H21B 132.1 . . ?
C20 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C22B C21 H21C 108.8 . . ?
C20 C21 H21C 107.7 . . ?
C22B C21 H21D 104.9 . . ?
C20 C21 H21D 109.1 . . ?
H21C C21 H21D 107.0 . . ?
C21 C22A C23 115.8(3) . . ?
C21 C22A H22A 108.3 . . ?
C23 C22A H22A 108.3 . . ?
C21 C22A H22B 108.3 . . ?
C23 C22A H22B 108.3 . . ?
H22A C22A H22B 107.4 . . ?
H22B C22A H23E 109.5 . . ?
C21 C22B C23 119.8(4) . . ?
C21 C22B H22C 107.4 . . ?
C23 C22B H22C 107.4 . . ?
C21 C22B H22D 107.4 . . ?
C23 C22B H22D 107.4 . . ?
H22C C22B H22D 106.9 . . ?
C22A C23 H23A 109.5 . . ?
C22A C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22B C23 H23C 114.8 . . ?
C22A C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22B C23 H23D 106.4 . . ?
C22B C23 H23E 112.6 . . ?
H23D C23 H23E 109.5 . . ?
C22B C23 H23F 109.3 . . ?
H23D C23 H23F 109.5 . . ?
H23E C23 H23F 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
O1 C1 C2 C3 -179.9(2) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
O1 C1 C2 C7 0.5(4) . . . . ?
C6 C1 C2 C7 179.5(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C7 C2 C3 C4 179.4(3) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
O1 C1 C6 C5 179.9(3) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C3 C2 C7 O3 0.6(4) . . . . ?
C1 C2 C7 O3 -179.7(2) . . . . ?
C3 C2 C7 O2 -180.0(2) . . . . ?
C1 C2 C7 O2 -0.3(3) . . . . ?
C20 P1 C8 C9 -174.3(2) . . . . ?
C12 P1 C8 C9 -56.2(3) . . . . ?
C16 P1 C8 C9 65.2(3) . . . . ?
P1 C8 C9 C10 170.6(2) . . . . ?
C8 C9 C10 C11 -175.8(3) . . . . ?
C20 P1 C12 C13 -160.8(2) . . . . ?
C8 P1 C12 C13 80.6(2) . . . . ?
C16 P1 C12 C13 -41.1(2) . . . . ?
P1 C12 C13 C14 179.9(2) . . . . ?
C12 C13 C14 C15 -179.4(3) . . . . ?
C20 P1 C16 C17 55.5(2) . . . . ?
C12 P1 C16 C17 -62.5(2) . . . . ?
C8 P1 C16 C17 174.5(2) . . . . ?
P1 C16 C17 C18 171.4(2) . . . . ?
C16 C17 C18 C19 55.7(5) . . . . ?
C12 P1 C20 C21 176.0(2) . . . . ?
C8 P1 C20 C21 -63.0(3) . . . . ?
C16 P1 C20 C21 57.0(3) . . . . ?
P1 C20 C21 C22A -163.6(3) . . . . ?
P1 C20 C21 C22B -114.0(5) . . . . ?
C22B C21 C22A C23 -46.6(4) . . . . ?
C20 C21 C22A C23 58.9(6) . . . . ?
C22A C21 C22B C23 51.8(5) . . . . ?
C20 C21 C22B C23 -46.7(8) . . . . ?
C21 C22B C23 C22A -50.1(5) . . . . ?
C21 C22A C23 C22B 47.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        68.25
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 950650'