# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# 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.
#
#  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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_sb29
#TrackingRef 'sb29.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Cl N3 O4'
_chemical_formula_weight         403.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.1105(16)
_cell_length_b                   8.8677(18)
_cell_length_c                   14.245(3)
_cell_angle_alpha                98.63(3)
_cell_angle_beta                 96.32(3)
_cell_angle_gamma                110.67(3)
_cell_volume                     932.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    108(2)
_cell_measurement_reflns_used    3367
_cell_measurement_theta_min      1.4687
_cell_measurement_theta_max      31.2948

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_process_details   Crystalclear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      108(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku saturn 724'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10726
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3166
_reflns_number_gt                3012
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0628P)^2^+1.1930P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3166
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.1656
_refine_ls_wR_factor_gt          0.1633
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_restrained_S_all      1.220
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.73019(11) 0.78522(9) 0.40144(6) 0.0297(3) Uani 1 1 d . . .
O1 O 0.2906(3) -0.1706(3) 0.21463(16) 0.0276(5) Uani 1 1 d . . .
O2 O 0.6459(3) 0.3189(3) 0.15617(17) 0.0321(6) Uani 1 1 d . . .
N1 N -0.1246(4) -0.2228(4) -0.2040(2) 0.0349(7) Uani 1 1 d . . .
H1X H -0.2126 -0.3151 -0.2205 0.042 Uiso 1 1 d . . .
H1Y H -0.1104 -0.1669 -0.2483 0.042 Uiso 1 1 d . . .
N2 N 0.4719(3) 0.0696(3) 0.18209(18) 0.0222(6) Uani 1 1 d . . .
N3 N 0.8930(3) 0.3829(3) 0.61964(18) 0.0210(6) Uani 1 1 d . . .
C1 C 0.3233(4) -0.0783(4) 0.1565(2) 0.0219(7) Uani 1 1 d . . .
C2 C 0.2123(4) -0.1142(4) 0.0622(2) 0.0206(7) Uani 1 1 d . . .
C3 C 0.0658(4) -0.2602(4) 0.0312(2) 0.0214(7) Uani 1 1 d . . .
H3 H 0.0397 -0.3383 0.0718 0.026 Uiso 1 1 calc R . .
C4 C -0.0440(4) -0.2959(4) -0.0573(2) 0.0221(7) Uani 1 1 d . . .
H4 H -0.1431 -0.3979 -0.0765 0.026 Uiso 1 1 calc R . .
C5 C -0.0107(4) -0.1839(4) -0.1185(2) 0.0225(7) Uani 1 1 d . . .
C6 C 0.1398(4) -0.0307(4) -0.0891(2) 0.0199(7) Uani 1 1 d . . .
C7 C 0.1813(4) 0.0913(4) -0.1465(2) 0.0234(7) Uani 1 1 d . . .
H7 H 0.1069 0.0727 -0.2068 0.028 Uiso 1 1 calc R . .
C8 C 0.3280(4) 0.2360(4) -0.1156(2) 0.0263(7) Uani 1 1 d . . .
H8 H 0.3541 0.3156 -0.1553 0.032 Uiso 1 1 calc R . .
C9 C 0.4390(4) 0.2678(4) -0.0269(2) 0.0244(7) Uani 1 1 d . . .
H9 H 0.5405 0.3678 -0.0069 0.029 Uiso 1 1 calc R . .
C10 C 0.4008(4) 0.1533(4) 0.0316(2) 0.0222(7) Uani 1 1 d . . .
C11 C 0.2519(4) 0.0027(4) 0.0019(2) 0.0200(7) Uani 1 1 d . . .
C12 C 0.5170(4) 0.1904(4) 0.1261(2) 0.0227(7) Uani 1 1 d . . .
C13 C 0.5851(4) 0.1081(4) 0.2772(2) 0.0256(7) Uani 1 1 d . . .
H13A H 0.7108 0.1722 0.2731 0.031 Uiso 1 1 calc R . .
H13B H 0.5804 0.0045 0.2970 0.031 Uiso 1 1 calc R . .
C14 C 0.5220(4) 0.2073(4) 0.3530(2) 0.0256(7) Uani 1 1 d . . .
H14A H 0.5101 0.3025 0.3286 0.031 Uiso 1 1 calc R . .
H14B H 0.4026 0.1372 0.3633 0.031 Uiso 1 1 calc R . .
C15 C 0.6503(4) 0.2685(4) 0.4478(2) 0.0212(7) Uani 1 1 d . . .
C16 C 0.7253(4) 0.4351(4) 0.4909(2) 0.0251(7) Uani 1 1 d . . .
H16 H 0.6930 0.5120 0.4611 0.030 Uiso 1 1 calc R . .
C17 C 0.8453(4) 0.4890(4) 0.5758(2) 0.0250(7) Uani 1 1 d . . .
H17 H 0.8954 0.6031 0.6042 0.030 Uiso 1 1 calc R . .
C18 C 0.8215(4) 0.2203(4) 0.5806(2) 0.0231(7) Uani 1 1 d . . .
H18 H 0.8543 0.1458 0.6126 0.028 Uiso 1 1 calc R . .
C19 C 0.7024(4) 0.1614(4) 0.4954(2) 0.0237(7) Uani 1 1 d . . .
H19 H 0.6547 0.0468 0.4684 0.028 Uiso 1 1 calc R . .
C20 C 1.0255(4) 0.4433(4) 0.7101(2) 0.0261(7) Uani 1 1 d . . .
H20A H 1.1404 0.4406 0.6965 0.031 Uiso 1 1 calc R . .
H20B H 0.9832 0.3727 0.7561 0.031 Uiso 1 1 calc R . .
H20C H 1.0408 0.5565 0.7377 0.031 Uiso 1 1 calc R . .
O10 O 0.3772(3) 0.5586(3) 0.25296(18) 0.0329(6) Uani 1 1 d . . .
H10X H 0.3444 0.6324 0.2348 0.039 Uiso 1 1 d . . .
H10Y H 0.4916 0.6135 0.2995 0.039 Uiso 1 1 d . . .
O20 O 0.9459(3) 0.8954(3) 0.61396(18) 0.0346(6) Uani 1 1 d . . .
H20X H 0.8961 0.8592 0.5569 0.042 Uiso 1 1 d . . .
H20Y H 1.0563 0.9877 0.6147 0.042 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
Cl1 0.0304(5) 0.0193(4) 0.0378(5) 0.0060(3) 0.0016(4) 0.0087(3)
O1 0.0293(13) 0.0283(12) 0.0246(12) 0.0097(10) 0.0014(10) 0.0095(10)
O2 0.0261(13) 0.0257(13) 0.0352(14) 0.0022(10) -0.0013(11) 0.0022(11)
N1 0.0338(17) 0.0306(16) 0.0331(16) 0.0068(13) -0.0001(14) 0.0049(13)
N2 0.0207(13) 0.0229(14) 0.0215(14) 0.0021(11) 0.0003(11) 0.0081(11)
N3 0.0202(13) 0.0203(13) 0.0208(13) 0.0032(11) 0.0057(11) 0.0054(11)
C1 0.0231(16) 0.0210(15) 0.0223(16) 0.0037(13) 0.0029(13) 0.0098(13)
C2 0.0213(16) 0.0207(15) 0.0218(16) 0.0029(13) 0.0053(13) 0.0104(13)
C3 0.0238(16) 0.0182(15) 0.0241(16) 0.0047(13) 0.0058(13) 0.0095(13)
C4 0.0202(16) 0.0192(15) 0.0249(17) 0.0021(13) 0.0028(13) 0.0064(13)
C5 0.0229(16) 0.0240(16) 0.0222(16) 0.0017(13) 0.0033(13) 0.0121(14)
C6 0.0204(16) 0.0179(15) 0.0221(16) 0.0025(12) 0.0057(13) 0.0081(13)
C7 0.0251(16) 0.0261(17) 0.0217(16) 0.0051(13) 0.0051(14) 0.0123(14)
C8 0.0292(18) 0.0251(17) 0.0298(18) 0.0119(14) 0.0120(15) 0.0117(14)
C9 0.0216(16) 0.0206(16) 0.0312(18) 0.0050(13) 0.0091(14) 0.0069(13)
C10 0.0202(16) 0.0181(15) 0.0283(17) 0.0007(13) 0.0056(14) 0.0085(13)
C11 0.0192(15) 0.0209(16) 0.0212(16) 0.0016(13) 0.0045(13) 0.0099(13)
C12 0.0204(16) 0.0229(16) 0.0263(17) 0.0028(13) 0.0055(14) 0.0104(14)
C13 0.0221(16) 0.0274(17) 0.0249(17) 0.0034(14) -0.0013(14) 0.0089(14)
C14 0.0258(17) 0.0275(17) 0.0249(17) 0.0023(14) 0.0019(14) 0.0137(14)
C15 0.0199(15) 0.0222(16) 0.0222(16) 0.0036(13) 0.0072(13) 0.0082(13)
C16 0.0306(18) 0.0229(16) 0.0257(17) 0.0078(13) 0.0064(14) 0.0132(14)
C17 0.0307(18) 0.0140(15) 0.0282(17) 0.0022(13) 0.0089(15) 0.0057(13)
C18 0.0245(16) 0.0174(15) 0.0272(17) 0.0043(13) 0.0058(14) 0.0074(13)
C19 0.0243(16) 0.0171(15) 0.0274(17) -0.0003(13) 0.0034(14) 0.0072(13)
C20 0.0257(17) 0.0245(17) 0.0228(17) -0.0004(13) 0.0016(14) 0.0061(14)
O10 0.0293(13) 0.0276(13) 0.0395(14) 0.0097(11) 0.0037(11) 0.0075(11)
O20 0.0359(14) 0.0301(13) 0.0359(14) 0.0136(11) 0.0059(11) 0.0073(11)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.235(4) . ?
O2 C12 1.221(4) . ?
N1 C5 1.363(4) . ?
N1 H1X 0.8526 . ?
N1 H1Y 0.8526 . ?
N2 C1 1.396(4) . ?
N2 C12 1.401(4) . ?
N2 C13 1.470(4) . ?
N3 C17 1.343(4) . ?
N3 C18 1.350(4) . ?
N3 C20 1.478(4) . ?
C1 C2 1.455(4) . ?
C2 C3 1.382(4) . ?
C2 C11 1.417(4) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.434(4) . ?
C6 C7 1.421(4) . ?
C6 C11 1.425(4) . ?
C7 C8 1.376(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.415(4) . ?
C10 C12 1.475(4) . ?
C13 C14 1.535(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.508(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.393(4) . ?
C15 C19 1.398(4) . ?
C16 C17 1.371(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.369(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O10 H10X 0.8508 . ?
O10 H10Y 0.9931 . ?
O20 H20X 0.8276 . ?
O20 H20Y 0.9743 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 H1X 120.7 . . ?
C5 N1 H1Y 125.6 . . ?
H1X N1 H1Y 113.3 . . ?
C1 N2 C12 124.9(3) . . ?
C1 N2 C13 118.4(3) . . ?
C12 N2 C13 116.6(3) . . ?
C17 N3 C18 120.1(3) . . ?
C17 N3 C20 120.4(3) . . ?
C18 N3 C20 119.5(3) . . ?
O1 C1 N2 119.0(3) . . ?
O1 C1 C2 123.3(3) . . ?
N2 C1 C2 117.7(3) . . ?
C3 C2 C11 119.3(3) . . ?
C3 C2 C1 120.8(3) . . ?
C11 C2 C1 120.0(3) . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 118.6(3) . . ?
N1 C5 C6 122.1(3) . . ?
C4 C5 C6 119.3(3) . . ?
C7 C6 C11 118.2(3) . . ?
C7 C6 C5 122.8(3) . . ?
C11 C6 C5 119.1(3) . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 C12 119.2(3) . . ?
C11 C10 C12 120.2(3) . . ?
C10 C11 C2 120.6(3) . . ?
C10 C11 C6 119.6(3) . . ?
C2 C11 C6 119.8(3) . . ?
O2 C12 N2 120.2(3) . . ?
O2 C12 C10 123.2(3) . . ?
N2 C12 C10 116.6(3) . . ?
N2 C13 C14 110.9(3) . . ?
N2 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C13 111.9(3) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C19 117.0(3) . . ?
C16 C15 C14 121.4(3) . . ?
C19 C15 C14 121.6(3) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N3 C17 C16 121.0(3) . . ?
N3 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
N3 C18 C19 120.8(3) . . ?
N3 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C15 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C15 C19 H19 119.7 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H10X O10 H10Y 108.6 . . ?
H20X O20 H20Y 106.9 . . ?

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
C12 N2 C1 O1 -175.3(3) . . . . ?
C13 N2 C1 O1 0.8(4) . . . . ?
C12 N2 C1 C2 3.7(5) . . . . ?
C13 N2 C1 C2 179.8(3) . . . . ?
O1 C1 C2 C3 -2.8(5) . . . . ?
N2 C1 C2 C3 178.3(3) . . . . ?
O1 C1 C2 C11 175.9(3) . . . . ?
N2 C1 C2 C11 -3.0(4) . . . . ?
C11 C2 C3 C4 0.0(5) . . . . ?
C1 C2 C3 C4 178.7(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 N1 -178.6(3) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
N1 C5 C6 C7 -0.1(5) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?
N1 C5 C6 C11 179.2(3) . . . . ?
C4 C5 C6 C11 0.3(4) . . . . ?
C11 C6 C7 C8 1.3(5) . . . . ?
C5 C6 C7 C8 -179.5(3) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C8 C9 C10 C11 1.1(5) . . . . ?
C8 C9 C10 C12 -178.6(3) . . . . ?
C9 C10 C11 C2 -179.7(3) . . . . ?
C12 C10 C11 C2 0.0(5) . . . . ?
C9 C10 C11 C6 -0.3(5) . . . . ?
C12 C10 C11 C6 179.4(3) . . . . ?
C3 C2 C11 C10 180.0(3) . . . . ?
C1 C2 C11 C10 1.3(5) . . . . ?
C3 C2 C11 C6 0.6(5) . . . . ?
C1 C2 C11 C6 -178.1(3) . . . . ?
C7 C6 C11 C10 -0.9(4) . . . . ?
C5 C6 C11 C10 179.9(3) . . . . ?
C7 C6 C11 C2 178.5(3) . . . . ?
C5 C6 C11 C2 -0.7(4) . . . . ?
C1 N2 C12 O2 177.1(3) . . . . ?
C13 N2 C12 O2 0.9(4) . . . . ?
C1 N2 C12 C10 -2.5(4) . . . . ?
C13 N2 C12 C10 -178.6(3) . . . . ?
C9 C10 C12 O2 0.6(5) . . . . ?
C11 C10 C12 O2 -179.0(3) . . . . ?
C9 C10 C12 N2 -179.8(3) . . . . ?
C11 C10 C12 N2 0.5(4) . . . . ?
C1 N2 C13 C14 -91.5(3) . . . . ?
C12 N2 C13 C14 84.9(3) . . . . ?
N2 C13 C14 C15 -172.1(3) . . . . ?
C13 C14 C15 C16 124.4(3) . . . . ?
C13 C14 C15 C19 -54.3(4) . . . . ?
C19 C15 C16 C17 0.4(5) . . . . ?
C14 C15 C16 C17 -178.3(3) . . . . ?
C18 N3 C17 C16 -0.6(5) . . . . ?
C20 N3 C17 C16 178.6(3) . . . . ?
C15 C16 C17 N3 -0.2(5) . . . . ?
C17 N3 C18 C19 1.1(5) . . . . ?
C20 N3 C18 C19 -178.1(3) . . . . ?
N3 C18 C19 C15 -0.9(5) . . . . ?
C16 C15 C19 C18 0.1(5) . . . . ?
C14 C15 C19 C18 178.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1X O10 0.85 2.05 2.882(4) 166.2 2
N1 H1Y O20 0.85 2.17 2.978(4) 158.2 1_444
O10 H10X O1 0.85 2.00 2.838(3) 170.0 1_565
O10 H10Y Cl1 0.99 2.19 3.168(3) 166.9 .
O20 H20X Cl1 0.83 2.33 3.150(3) 170.6 .
O20 H20Y Cl1 0.97 2.21 3.167(3) 168.2 2_776

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         1.018
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 924757'
#######################################################################
#
#                 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_sbpf6
#TrackingRef 'sbpf6.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 F6 N3 O2 P'
_chemical_formula_weight         505.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.8081(4)
_cell_length_b                   9.2489(4)
_cell_length_c                   14.9085(6)
_cell_angle_alpha                85.580(2)
_cell_angle_beta                 89.039(2)
_cell_angle_gamma                62.137(2)
_cell_volume                     1070.27(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4638
_cell_measurement_theta_min      8.336
_cell_measurement_theta_max      64.119

_exptl_crystal_description       Plate
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    1.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5895
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Duo'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7357
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         8.34
_diffrn_reflns_theta_max         63.95
_reflns_number_total             3360
_reflns_number_gt                3133
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
All non-H ANIS, all H calc and ride, no solvent, no disorder.
Weak, high angle, reflections removed using OMIT -2 128 command.
;

_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^)+(0.0768P)^2^+1.0489P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3360
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6927(3) 0.7292(3) 0.13126(14) 0.0413(5) Uani 1 1 d . . .
O2 O 0.8827(3) 0.9663(3) 0.32577(13) 0.0400(5) Uani 1 1 d . . .
N1 N 1.3299(3) 0.7116(3) -0.09337(15) 0.0339(5) Uani 1 1 d . . .
N2 N 0.7820(3) 0.8584(3) 0.22491(14) 0.0302(5) Uani 1 1 d . . .
N3 N 0.2429(3) 0.7589(3) 0.47868(14) 0.0293(5) Uani 1 1 d . . .
C1 C 0.7957(3) 0.7793(3) 0.14557(18) 0.0301(6) Uani 1 1 d . . .
C2 C 0.9334(3) 0.7640(3) 0.08550(17) 0.0278(6) Uani 1 1 d . . .
C3 C 0.9502(3) 0.6952(3) 0.00486(18) 0.0317(6) Uani 1 1 d . . .
H3A H 0.8709 0.6581 -0.0109 0.038 Uiso 1 1 calc R . .
C4 C 1.0811(4) 0.6785(3) -0.05414(18) 0.0333(6) Uani 1 1 d . . .
H4A H 1.0892 0.6293 -0.1088 0.040 Uiso 1 1 calc R . .
C5 C 1.2000(3) 0.7320(3) -0.03524(18) 0.0302(6) Uani 1 1 d . . .
C6 C 1.1787(3) 0.8154(3) 0.04595(17) 0.0284(6) Uani 1 1 d . . .
C7 C 1.2721(3) 0.8985(3) 0.06590(19) 0.0325(6) Uani 1 1 d . . .
H7A H 1.3548 0.8997 0.0246 0.039 Uiso 1 1 calc R . .
C8 C 1.2470(4) 0.9772(3) 0.1428(2) 0.0357(6) Uani 1 1 d . . .
H8A H 1.3112 1.0331 0.1537 0.043 Uiso 1 1 calc R . .
C9 C 1.1282(4) 0.9764(3) 0.20526(19) 0.0336(6) Uani 1 1 d . . .
H9A H 1.1160 1.0263 0.2601 0.040 Uiso 1 1 calc R . .
C10 C 1.0282(3) 0.9027(3) 0.18731(18) 0.0293(6) Uani 1 1 d . . .
C11 C 1.0475(3) 0.8254(3) 0.10657(17) 0.0267(5) Uani 1 1 d . . .
C12 C 0.8957(3) 0.9117(3) 0.25120(18) 0.0306(6) Uani 1 1 d . . .
C13 C 0.6416(3) 0.8751(3) 0.28501(18) 0.0329(6) Uani 1 1 d . . .
H13A H 0.5399 0.8946 0.2485 0.040 Uiso 1 1 calc R . .
H13B H 0.6092 0.9712 0.3204 0.040 Uiso 1 1 calc R . .
C14 C 0.6943(4) 0.7208(4) 0.34934(19) 0.0368(7) Uani 1 1 d . . .
H14A H 0.7467 0.6218 0.3152 0.044 Uiso 1 1 calc R . .
H14B H 0.7801 0.7126 0.3942 0.044 Uiso 1 1 calc R . .
C15 C 0.5372(3) 0.7315(3) 0.39617(18) 0.0307(6) Uani 1 1 d . . .
C16 C 0.4286(4) 0.6834(4) 0.3559(2) 0.0395(7) Uani 1 1 d . . .
H16A H 0.4555 0.6400 0.2986 0.047 Uiso 1 1 calc R . .
C17 C 0.2831(4) 0.6980(4) 0.3980(2) 0.0374(7) Uani 1 1 d . . .
H17A H 0.2101 0.6645 0.3697 0.045 Uiso 1 1 calc R . .
C18 C 0.3439(4) 0.8086(4) 0.51933(18) 0.0337(6) Uani 1 1 d . . .
H18A H 0.3134 0.8531 0.5762 0.040 Uiso 1 1 calc R . .
C19 C 0.4907(4) 0.7953(4) 0.47908(18) 0.0336(6) Uani 1 1 d . . .
H19A H 0.5613 0.8303 0.5085 0.040 Uiso 1 1 calc R . .
C20 C 1.3252(4) 0.6558(4) -0.1817(2) 0.0427(7) Uani 1 1 d . . .
H20A H 1.2100 0.7206 -0.2089 0.064 Uiso 1 1 calc R . .
H20B H 1.3533 0.5397 -0.1752 0.064 Uiso 1 1 calc R . .
H20C H 1.4092 0.6698 -0.2205 0.064 Uiso 1 1 calc R . .
C21 C 1.5063(4) 0.6646(4) -0.0623(2) 0.0398(7) Uani 1 1 d . . .
H21A H 1.5137 0.6474 0.0035 0.060 Uiso 1 1 calc R . .
H21B H 1.5355 0.7522 -0.0816 0.060 Uiso 1 1 calc R . .
H21C H 1.5870 0.5630 -0.0883 0.060 Uiso 1 1 calc R . .
C22 C 0.0869(4) 0.7707(4) 0.5232(2) 0.0420(7) Uani 1 1 d . . .
H22A H -0.0128 0.8327 0.4826 0.063 Uiso 1 1 calc R . .
H22B H 0.0697 0.8270 0.5785 0.063 Uiso 1 1 calc R . .
H22C H 0.1002 0.6603 0.5382 0.063 Uiso 1 1 calc R . .
P1 P 0.19158(8) 0.35231(7) 0.31161(4) 0.0236(2) Uani 1 1 d . . .
F1 F 0.2537(3) 0.2827(3) 0.21770(12) 0.0541(5) Uani 1 1 d . . .
F2 F 0.2600(2) 0.1688(2) 0.35926(12) 0.0462(5) Uani 1 1 d . . .
F3 F 0.1221(3) 0.5354(2) 0.26984(12) 0.0516(5) Uani 1 1 d . . .
F4 F 0.3743(2) 0.3430(2) 0.33267(12) 0.0455(5) Uani 1 1 d . . .
F5 F 0.0090(2) 0.3602(2) 0.29476(11) 0.0416(4) Uani 1 1 d . . .
F6 F 0.1294(2) 0.4214(2) 0.40988(11) 0.0423(4) Uani 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
O1 0.0373(11) 0.0577(13) 0.0407(11) -0.0164(10) 0.0129(9) -0.0305(10)
O2 0.0426(11) 0.0535(12) 0.0297(10) -0.0169(9) 0.0140(8) -0.0258(10)
N1 0.0318(12) 0.0423(13) 0.0299(12) -0.0086(10) 0.0140(10) -0.0190(10)
N2 0.0286(11) 0.0389(12) 0.0253(11) -0.0080(9) 0.0125(9) -0.0173(10)
N3 0.0312(12) 0.0351(12) 0.0290(11) -0.0045(9) 0.0087(9) -0.0218(10)
C1 0.0291(14) 0.0338(14) 0.0286(13) -0.0053(11) 0.0074(11) -0.0154(11)
C2 0.0277(13) 0.0296(13) 0.0243(13) -0.0026(10) 0.0067(10) -0.0120(11)
C3 0.0301(14) 0.0343(14) 0.0303(14) -0.0066(11) 0.0067(11) -0.0144(11)
C4 0.0366(15) 0.0361(14) 0.0247(13) -0.0077(11) 0.0088(11) -0.0143(12)
C5 0.0307(14) 0.0284(13) 0.0279(13) -0.0010(10) 0.0093(11) -0.0113(11)
C6 0.0268(13) 0.0261(13) 0.0270(13) -0.0002(10) 0.0064(10) -0.0084(11)
C7 0.0256(13) 0.0334(14) 0.0382(15) 0.0028(11) 0.0073(11) -0.0146(11)
C8 0.0314(14) 0.0372(15) 0.0422(16) -0.0031(12) 0.0049(12) -0.0192(12)
C9 0.0331(14) 0.0349(14) 0.0358(14) -0.0079(11) 0.0061(11) -0.0179(12)
C10 0.0278(13) 0.0302(13) 0.0282(13) -0.0049(10) 0.0079(10) -0.0120(11)
C11 0.0251(13) 0.0257(12) 0.0263(13) -0.0005(10) 0.0072(10) -0.0097(10)
C12 0.0296(14) 0.0341(14) 0.0287(14) -0.0069(11) 0.0098(11) -0.0149(11)
C13 0.0269(13) 0.0423(15) 0.0303(14) -0.0069(11) 0.0134(11) -0.0165(12)
C14 0.0305(14) 0.0468(16) 0.0321(14) -0.0030(12) 0.0108(11) -0.0175(13)
C15 0.0282(13) 0.0336(14) 0.0296(13) -0.0012(11) 0.0071(11) -0.0144(11)
C16 0.0409(16) 0.0489(17) 0.0352(15) -0.0205(13) 0.0145(12) -0.0241(14)
C17 0.0417(16) 0.0457(16) 0.0387(15) -0.0152(12) 0.0090(12) -0.0305(14)
C18 0.0390(15) 0.0468(16) 0.0241(13) -0.0095(11) 0.0084(11) -0.0267(13)
C19 0.0341(15) 0.0466(16) 0.0305(14) -0.0067(12) 0.0061(11) -0.0272(13)
C20 0.0457(17) 0.0528(18) 0.0328(15) -0.0129(13) 0.0184(13) -0.0250(15)
C21 0.0275(14) 0.0441(16) 0.0439(16) -0.0034(13) 0.0137(12) -0.0139(12)
C22 0.0387(16) 0.0582(19) 0.0411(16) -0.0048(14) 0.0140(13) -0.0329(15)
P1 0.0242(4) 0.0278(4) 0.0260(4) -0.0079(3) 0.0090(3) -0.0176(3)
F1 0.0690(13) 0.0743(13) 0.0397(10) -0.0245(9) 0.0264(9) -0.0487(11)
F2 0.0455(10) 0.0381(9) 0.0570(11) 0.0028(8) 0.0025(8) -0.0222(8)
F3 0.0722(13) 0.0451(10) 0.0490(11) 0.0066(8) -0.0127(9) -0.0381(10)
F4 0.0359(9) 0.0622(11) 0.0509(10) -0.0048(8) 0.0094(8) -0.0336(9)
F5 0.0373(9) 0.0513(10) 0.0456(10) -0.0079(8) 0.0024(7) -0.0280(8)
F6 0.0426(9) 0.0590(11) 0.0361(9) -0.0172(8) 0.0136(7) -0.0311(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.224(3) . ?
O2 C12 1.238(3) . ?
N1 C5 1.373(3) . ?
N1 C20 1.460(4) . ?
N1 C21 1.477(4) . ?
N2 C12 1.381(3) . ?
N2 C1 1.412(3) . ?
N2 C13 1.470(3) . ?
N3 C17 1.339(4) . ?
N3 C18 1.347(3) . ?
N3 C22 1.477(3) . ?
C1 C2 1.455(4) . ?
C2 C3 1.377(4) . ?
C2 C11 1.415(4) . ?
C3 C4 1.395(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.391(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.448(4) . ?
C6 C7 1.411(4) . ?
C6 C11 1.427(4) . ?
C7 C8 1.365(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.392(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.382(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.414(4) . ?
C10 C12 1.470(4) . ?
C13 C14 1.535(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.504(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C19 1.383(4) . ?
C15 C16 1.390(4) . ?
C16 C17 1.371(4) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C19 1.373(4) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
P1 F1 1.5678(17) . ?
P1 F3 1.5850(18) . ?
P1 F5 1.5987(16) . ?
P1 F4 1.6058(17) . ?
P1 F2 1.6187(17) . ?
P1 F6 1.6264(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C20 118.2(2) . . ?
C5 N1 C21 122.8(2) . . ?
C20 N1 C21 112.5(2) . . ?
C12 N2 C1 124.5(2) . . ?
C12 N2 C13 118.8(2) . . ?
C1 N2 C13 116.6(2) . . ?
C17 N3 C18 120.5(2) . . ?
C17 N3 C22 119.5(2) . . ?
C18 N3 C22 120.0(2) . . ?
O1 C1 N2 118.9(2) . . ?
O1 C1 C2 124.3(2) . . ?
N2 C1 C2 116.7(2) . . ?
C3 C2 C11 118.8(2) . . ?
C3 C2 C1 120.1(2) . . ?
C11 C2 C1 121.1(2) . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 122.0(2) . . ?
C5 C4 H4A 119.0 . . ?
C3 C4 H4A 119.0 . . ?
N1 C5 C4 121.1(2) . . ?
N1 C5 C6 121.0(2) . . ?
C4 C5 C6 117.9(2) . . ?
C7 C6 C11 117.4(2) . . ?
C7 C6 C5 123.7(2) . . ?
C11 C6 C5 118.8(2) . . ?
C8 C7 C6 122.0(2) . . ?
C8 C7 H7A 119.0 . . ?
C6 C7 H7A 119.0 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8A 119.7 . . ?
C9 C8 H8A 119.7 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 C12 119.3(2) . . ?
C11 C10 C12 120.1(2) . . ?
C10 C11 C2 119.8(2) . . ?
C10 C11 C6 119.4(2) . . ?
C2 C11 C6 120.9(2) . . ?
O2 C12 N2 120.0(2) . . ?
O2 C12 C10 122.4(2) . . ?
N2 C12 C10 117.5(2) . . ?
N2 C13 C14 111.4(2) . . ?
N2 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N2 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 108.8(2) . . ?
C15 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C19 C15 C16 117.2(2) . . ?
C19 C15 C14 121.8(2) . . ?
C16 C15 C14 121.0(2) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
N3 C17 C16 120.6(3) . . ?
N3 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
N3 C18 C19 120.4(2) . . ?
N3 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C18 C19 C15 120.8(2) . . ?
C18 C19 H19A 119.6 . . ?
C15 C19 H19A 119.6 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F1 P1 F3 91.83(11) . . ?
F1 P1 F5 90.73(10) . . ?
F3 P1 F5 91.06(10) . . ?
F1 P1 F4 91.18(10) . . ?
F3 P1 F4 90.06(10) . . ?
F5 P1 F4 177.76(9) . . ?
F1 P1 F2 91.07(10) . . ?
F3 P1 F2 177.09(10) . . ?
F5 P1 F2 89.10(9) . . ?
F4 P1 F2 89.69(9) . . ?
F1 P1 F6 179.02(11) . . ?
F3 P1 F6 89.10(10) . . ?
F5 P1 F6 89.59(9) . . ?
F4 P1 F6 88.49(9) . . ?
F2 P1 F6 88.00(10) . . ?

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
C12 N2 C1 O1 176.1(3) . . . . ?
C13 N2 C1 O1 -0.2(4) . . . . ?
C12 N2 C1 C2 -4.3(4) . . . . ?
C13 N2 C1 C2 179.4(2) . . . . ?
O1 C1 C2 C3 2.6(4) . . . . ?
N2 C1 C2 C3 -177.0(2) . . . . ?
O1 C1 C2 C11 179.8(3) . . . . ?
N2 C1 C2 C11 0.3(4) . . . . ?
C11 C2 C3 C4 2.8(4) . . . . ?
C1 C2 C3 C4 -179.9(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C20 N1 C5 C4 9.3(4) . . . . ?
C21 N1 C5 C4 -140.3(3) . . . . ?
C20 N1 C5 C6 -168.3(2) . . . . ?
C21 N1 C5 C6 42.1(4) . . . . ?
C3 C4 C5 N1 178.7(2) . . . . ?
C3 C4 C5 C6 -3.6(4) . . . . ?
N1 C5 C6 C7 8.2(4) . . . . ?
C4 C5 C6 C7 -169.5(3) . . . . ?
N1 C5 C6 C11 -176.6(2) . . . . ?
C4 C5 C6 C11 5.7(4) . . . . ?
C11 C6 C7 C8 4.1(4) . . . . ?
C5 C6 C7 C8 179.3(3) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C8 C9 C10 -3.4(4) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C8 C9 C10 C12 -176.2(2) . . . . ?
C9 C10 C11 C2 -174.2(2) . . . . ?
C12 C10 C11 C2 3.1(4) . . . . ?
C9 C10 C11 C6 3.7(4) . . . . ?
C12 C10 C11 C6 -179.0(2) . . . . ?
C3 C2 C11 C10 177.4(2) . . . . ?
C1 C2 C11 C10 0.1(4) . . . . ?
C3 C2 C11 C6 -0.5(4) . . . . ?
C1 C2 C11 C6 -177.8(2) . . . . ?
C7 C6 C11 C10 -6.2(4) . . . . ?
C5 C6 C11 C10 178.3(2) . . . . ?
C7 C6 C11 C2 171.7(2) . . . . ?
C5 C6 C11 C2 -3.8(4) . . . . ?
C1 N2 C12 O2 -173.4(2) . . . . ?
C13 N2 C12 O2 2.9(4) . . . . ?
C1 N2 C12 C10 7.4(4) . . . . ?
C13 N2 C12 C10 -176.3(2) . . . . ?
C9 C10 C12 O2 -8.6(4) . . . . ?
C11 C10 C12 O2 174.1(2) . . . . ?
C9 C10 C12 N2 170.6(2) . . . . ?
C11 C10 C12 N2 -6.7(4) . . . . ?
C12 N2 C13 C14 -91.3(3) . . . . ?
C1 N2 C13 C14 85.2(3) . . . . ?
N2 C13 C14 C15 -169.2(2) . . . . ?
C13 C14 C15 C19 -93.5(3) . . . . ?
C13 C14 C15 C16 83.9(3) . . . . ?
C19 C15 C16 C17 -0.6(4) . . . . ?
C14 C15 C16 C17 -178.2(3) . . . . ?
C18 N3 C17 C16 0.7(4) . . . . ?
C22 N3 C17 C16 -179.0(3) . . . . ?
C15 C16 C17 N3 0.0(5) . . . . ?
C17 N3 C18 C19 -0.9(4) . . . . ?
C22 N3 C18 C19 178.8(3) . . . . ?
N3 C18 C19 C15 0.3(4) . . . . ?
C16 C15 C19 C18 0.5(4) . . . . ?
C14 C15 C19 C18 178.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        63.95
_diffrn_measured_fraction_theta_full 0.951
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.063


_database_code_depnum_ccdc_archive 'CCDC 924758'