data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177

_publ_section_title              
;Synthesis of Functionalized Bisphosphonates via Click
Chemistry
;
loop_
_publ_author_name
S.Osipov
E.Lork
I.L.Odinets
G.-V.Roschenthaler
H.Skarpos
;
D.V.Vorob'eva
;
_publ_contact_author_name        'Sergey Osipov'
_publ_contact_author_email       OSIPOV@INEOS.AC.RU

# Attachment 'HS4new.CIF'

data_hs4
_database_code_depnum_ccdc_archive 'CCDC 645541'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H40 N6 O6 P2'
_chemical_formula_sum            'C29 H40 N6 O6 P2'
_chemical_formula_weight         630.61

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.615(6)
_cell_length_b                   12.829(4)
_cell_length_c                   14.996(5)
_cell_angle_alpha                88.06(3)
_cell_angle_beta                 78.28(4)
_cell_angle_gamma                75.70(4)
_cell_volume                     1572.3(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      2.127
_cell_measurement_theta_max      12.406

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 197
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        'random variation +/-2.0'
_diffrn_reflns_number            6834
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0831
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5524
_reflns_number_gt                3621
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Siemens XSCANS'
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond, Crystal Impact'
_computing_publication_material  'Siemens SHELXTL'

_refine_special_details          
;
Two of the four OEt-groups are disordered. O3-C3-C4 with O3-C30-C40 and
O6-C7-C8 with O6-C70-C80, 50% occupation for each Et-group. The 1-2, 2-3
and 1-3 bonds for all OEt-groups were restrained with the SADI command of
SHELX to get reasonable distances for the disordered parts.

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^)+(0.1077P)^2^+0.4189P] 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    refU
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5524
_refine_ls_number_parameters     428
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1940
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.15774(14) 0.06053(8) 0.34473(7) 0.0288(3) Uani 1 1 d . A .
O1 O 0.1878(4) 0.0480(2) 0.43721(19) 0.0385(7) Uani 1 1 d . . .
O2 O -0.0166(3) 0.1285(2) 0.33665(18) 0.0350(7) Uani 1 1 d D . .
C1 C -0.1516(6) 0.1461(5) 0.4101(4) 0.095(3) Uani 1 1 d D . .
H1A H -0.1145 0.1554 0.4669 0.057(4) Uiso 1 1 calc R . .
H1B H -0.1975 0.0821 0.4168 0.057(4) Uiso 1 1 calc R . .
C2 C -0.2793(5) 0.2407(4) 0.3975(4) 0.0570(14) Uani 1 1 d D . .
H2A H -0.2321 0.3030 0.3847 0.091(7) Uiso 1 1 calc R . .
H2B H -0.3645 0.2548 0.4529 0.091(7) Uiso 1 1 calc R . .
H2C H -0.3273 0.2277 0.3462 0.091(7) Uiso 1 1 calc R . .
O3 O 0.1762(4) -0.0495(2) 0.29348(19) 0.0394(8) Uani 1 1 d D . .
C3 C 0.0799(8) -0.1182(5) 0.3375(5) 0.033(2) Uani 0.50 1 d PD A 1
H3A H -0.0040 -0.1216 0.3021 0.057(4) Uiso 0.50 1 calc PR A 1
H3B H 0.0228 -0.0880 0.3987 0.057(4) Uiso 0.50 1 calc PR A 1
C4 C 0.1791(13) -0.2271(4) 0.3467(6) 0.044(3) Uani 0.50 1 d PD A 1
H4A H 0.2537 -0.2251 0.3877 0.091(7) Uiso 0.50 1 calc PR A 1
H4B H 0.2426 -0.2550 0.2868 0.091(7) Uiso 0.50 1 calc PR A 1
H4C H 0.1073 -0.2740 0.3719 0.091(7) Uiso 0.50 1 calc PR A 1
C30 C 0.2113(9) -0.1525(5) 0.3311(6) 0.039(2) Uani 0.50 1 d PD A 2
H30A H 0.2642 -0.1501 0.3834 0.057(4) Uiso 0.50 1 calc PR A 2
H30B H 0.2892 -0.2033 0.2849 0.057(4) Uiso 0.50 1 calc PR A 2
C40 C 0.0637(14) -0.1919(8) 0.3615(8) 0.060(3) Uani 0.50 1 d PD A 2
H40A H -0.0145 -0.1412 0.4065 0.091(7) Uiso 0.50 1 calc PR A 2
H40B H 0.0927 -0.2625 0.3893 0.091(7) Uiso 0.50 1 calc PR A 2
H40C H 0.0143 -0.1984 0.3092 0.091(7) Uiso 0.50 1 calc PR A 2
C9 C 0.2927(5) 0.1290(3) 0.2667(3) 0.0245(9) Uani 1 1 d . . .
P2 P 0.49210(14) 0.03467(8) 0.22714(8) 0.0322(3) Uani 1 1 d . A .
O4 O 0.5016(4) -0.0310(2) 0.1480(2) 0.0455(8) Uani 1 1 d . . .
O5 O 0.6121(4) 0.1102(3) 0.2130(2) 0.0494(9) Uani 1 1 d D . .
C5 C 0.7609(6) 0.0971(4) 0.1491(3) 0.0544(14) Uani 1 1 d D A .
H5A H 0.7494 0.0677 0.0913 0.057(4) Uiso 1 1 calc R . .
H5B H 0.8483 0.0449 0.1724 0.057(4) Uiso 1 1 calc R . .
C6 C 0.8074(7) 0.1992(4) 0.1319(3) 0.0654(17) Uani 1 1 d D . .
H6A H 0.7240 0.2497 0.1056 0.091(7) Uiso 1 1 calc R A .
H6B H 0.9129 0.1870 0.0892 0.091(7) Uiso 1 1 calc R . .
H6C H 0.8166 0.2292 0.1893 0.091(7) Uiso 1 1 calc R . .
O6 O 0.5285(6) -0.0309(4) 0.3104(3) 0.0952(18) Uani 1 1 d D . .
C7 C 0.6085(13) -0.1341(5) 0.3307(5) 0.050(3) Uani 0.50 1 d PD A 1
H7A H 0.7222 -0.1507 0.2953 0.057(4) Uiso 0.50 1 calc PR A 1
H7B H 0.5533 -0.1862 0.3117 0.057(4) Uiso 0.50 1 calc PR A 1
C70 C 0.6136(16) -0.0546(9) 0.3810(7) 0.121(8) Uani 0.50 1 d PD A 2
H70A H 0.5492 -0.0114 0.4356 0.057(4) Uiso 0.50 1 calc PR A 2
H70B H 0.7185 -0.0334 0.3633 0.057(4) Uiso 0.50 1 calc PR A 2
C8 C 0.612(4) -0.1472(11) 0.4277(9) 0.081(5) Uani 0.50 1 d PD A 1
H8A H 0.5163 -0.0970 0.4635 0.091(7) Uiso 0.50 1 calc PR A 1
H8B H 0.7119 -0.1322 0.4395 0.091(7) Uiso 0.50 1 calc PR A 1
H8C H 0.6089 -0.2211 0.4451 0.091(7) Uiso 0.50 1 calc PR A 1
C80 C 0.647(4) -0.1683(10) 0.4043(13) 0.081(5) Uani 0.50 1 d PD A 2
H80A H 0.5452 -0.1920 0.4149 0.091(7) Uiso 0.50 1 calc PR A 2
H80B H 0.6929 -0.1785 0.4595 0.091(7) Uiso 0.50 1 calc PR A 2
H80C H 0.7256 -0.2106 0.3540 0.091(7) Uiso 0.50 1 calc PR A 2
C10 C 0.3170(5) 0.2249(3) 0.3204(3) 0.0270(9) Uani 1 1 d . A .
H10A H 0.3647 0.1955 0.3734 0.057(4) Uiso 1 1 calc R . .
H10B H 0.3975 0.2580 0.2803 0.057(4) Uiso 1 1 calc R . .
C11 C 0.1651(5) 0.3119(3) 0.3540(3) 0.0269(9) Uani 1 1 d . . .
N1 N 0.0854(5) 0.3197(3) 0.4428(2) 0.0352(9) Uani 1 1 d . A .
N2 N -0.0367(5) 0.4069(3) 0.4538(2) 0.0392(9) Uani 1 1 d . . .
N3 N -0.0320(4) 0.4551(3) 0.3724(2) 0.0310(8) Uani 1 1 d . A .
C12 C 0.0917(5) 0.3978(3) 0.3097(3) 0.0301(9) Uani 1 1 d . A .
H12 H 0.1213 0.4142 0.2473 0.051(4) Uiso 1 1 calc R . .
C13 C -0.1499(5) 0.5551(3) 0.3615(3) 0.0395(11) Uani 1 1 d . . .
H13A H -0.0948 0.6019 0.3192 0.057(4) Uiso 1 1 calc R A .
H13B H -0.1923 0.5931 0.4211 0.057(4) Uiso 1 1 calc R . .
C14 C -0.2904(5) 0.5352(3) 0.3248(3) 0.0341(10) Uani 1 1 d . A .
C15 C -0.2695(6) 0.5034(4) 0.2345(3) 0.0413(11) Uani 1 1 d . . .
H15 H -0.1661 0.4971 0.1952 0.051(4) Uiso 1 1 calc R A .
C16 C -0.3944(7) 0.4806(4) 0.2007(4) 0.0513(13) Uani 1 1 d . A .
H16 H -0.3771 0.4597 0.1386 0.051(4) Uiso 1 1 calc R . .
C17 C -0.5433(7) 0.4881(4) 0.2563(4) 0.0541(14) Uani 1 1 d . . .
H17 H -0.6289 0.4706 0.2333 0.051(4) Uiso 1 1 calc R A .
C18 C -0.5695(6) 0.5206(5) 0.3446(4) 0.0608(15) Uani 1 1 d . A .
H18 H -0.6740 0.5270 0.3826 0.051(4) Uiso 1 1 calc R . .
C19 C -0.4443(6) 0.5448(4) 0.3798(3) 0.0490(12) Uani 1 1 d . . .
H19 H -0.4642 0.5678 0.4415 0.051(4) Uiso 1 1 calc R A .
C20 C 0.2160(5) 0.1667(3) 0.1810(3) 0.0294(9) Uani 1 1 d . A .
H20A H 0.1954 0.1032 0.1540 0.057(4) Uiso 1 1 calc R . .
H20B H 0.1087 0.2179 0.2018 0.057(4) Uiso 1 1 calc R . .
C21 C 0.3152(5) 0.2191(3) 0.1074(3) 0.0266(9) Uani 1 1 d . . .
N4 N 0.3080(5) 0.3263(3) 0.1101(2) 0.0354(9) Uani 1 1 d . A .
N5 N 0.4019(5) 0.3512(3) 0.0353(2) 0.0363(9) Uani 1 1 d . . .
N6 N 0.4678(4) 0.2599(2) -0.0142(2) 0.0289(8) Uani 1 1 d . A .
C22 C 0.4172(5) 0.1772(3) 0.0278(3) 0.0292(9) Uani 1 1 d . A .
H22 H 0.4460 0.1046 0.0068 0.051(4) Uiso 1 1 calc R . .
C23 C 0.5789(5) 0.2600(3) -0.1036(3) 0.0321(10) Uani 1 1 d . . .
H23A H 0.5258 0.3170 -0.1415 0.057(4) Uiso 1 1 calc R A .
H23B H 0.5976 0.1900 -0.1350 0.057(4) Uiso 1 1 calc R . .
C24 C 0.7421(5) 0.2787(3) -0.0950(2) 0.0285(9) Uani 1 1 d . A .
C25 C 0.7561(5) 0.3796(3) -0.0737(3) 0.0327(10) Uani 1 1 d . . .
H25 H 0.6617 0.4380 -0.0634 0.051(4) Uiso 1 1 calc R A .
C26 C 0.9058(6) 0.3964(4) -0.0671(3) 0.0446(12) Uani 1 1 d . A .
H26 H 0.9137 0.4662 -0.0527 0.051(4) Uiso 1 1 calc R . .
C27 C 1.0440(6) 0.3122(4) -0.0813(3) 0.0491(13) Uani 1 1 d . . .
H27 H 1.1467 0.3238 -0.0765 0.051(4) Uiso 1 1 calc R A .
C28 C 1.0315(6) 0.2111(4) -0.1026(3) 0.0476(12) Uani 1 1 d . A .
H28 H 1.1261 0.1529 -0.1128 0.051(4) Uiso 1 1 calc R . .
C29 C 0.8822(6) 0.1944(4) -0.1090(3) 0.0402(11) Uani 1 1 d . . .
H29 H 0.8747 0.1245 -0.1233 0.051(4) Uiso 1 1 calc R A .

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 0.0343(6) 0.0276(6) 0.0271(6) 0.0036(4) -0.0014(5) -0.0168(5)
O1 0.0473(19) 0.0394(17) 0.0333(16) 0.0108(13) -0.0078(14) -0.0206(15)
O2 0.0314(17) 0.0451(17) 0.0284(15) -0.0002(13) 0.0010(13) -0.0149(14)
C1 0.036(3) 0.136(6) 0.082(4) 0.068(4) 0.024(3) -0.001(4)
C2 0.034(3) 0.072(4) 0.064(3) -0.018(3) 0.001(3) -0.018(3)
O3 0.056(2) 0.0284(15) 0.0370(17) -0.0005(12) 0.0043(15) -0.0272(15)
C3 0.050(6) 0.030(5) 0.027(4) 0.002(4) 0.003(4) -0.032(5)
C4 0.073(8) 0.030(5) 0.029(5) 0.005(4) 0.009(5) -0.028(5)
C30 0.039(6) 0.027(5) 0.051(6) 0.001(4) -0.003(5) -0.011(4)
C40 0.060(8) 0.078(9) 0.048(7) -0.002(6) 0.008(6) -0.042(7)
C9 0.026(2) 0.0222(19) 0.027(2) 0.0023(15) -0.0023(17) -0.0112(17)
P2 0.0326(7) 0.0262(6) 0.0355(6) 0.0035(4) -0.0003(5) -0.0087(5)
O4 0.045(2) 0.0298(16) 0.058(2) -0.0126(14) 0.0063(16) -0.0137(15)
O5 0.0345(18) 0.058(2) 0.053(2) -0.0237(16) 0.0172(15) -0.0255(16)
C5 0.050(3) 0.055(3) 0.051(3) -0.013(2) 0.017(2) -0.020(3)
C6 0.073(4) 0.095(4) 0.044(3) 0.007(3) -0.007(3) -0.055(4)
O6 0.069(3) 0.110(4) 0.074(3) 0.051(3) -0.001(2) 0.021(3)
C7 0.064(7) 0.032(5) 0.039(5) 0.001(4) -0.006(5) 0.013(5)
C70 0.072(10) 0.075(10) 0.195(19) -0.079(12) 0.047(12) -0.031(9)
C8 0.152(15) 0.027(6) 0.082(9) 0.006(6) -0.074(11) -0.013(7)
C80 0.152(15) 0.027(6) 0.082(9) 0.006(6) -0.074(11) -0.013(7)
C10 0.031(2) 0.0240(19) 0.029(2) 0.0001(16) -0.0067(18) -0.0126(18)
C11 0.026(2) 0.028(2) 0.031(2) -0.0006(17) -0.0066(17) -0.0128(18)
N1 0.042(2) 0.0316(19) 0.034(2) -0.0033(15) -0.0037(17) -0.0143(18)
N2 0.041(2) 0.038(2) 0.040(2) -0.0061(17) -0.0036(18) -0.0154(19)
N3 0.029(2) 0.0315(18) 0.0342(19) -0.0054(15) -0.0056(16) -0.0111(16)
C12 0.029(2) 0.032(2) 0.032(2) -0.0007(18) -0.0042(18) -0.0141(19)
C13 0.034(3) 0.030(2) 0.055(3) -0.009(2) -0.010(2) -0.006(2)
C14 0.029(2) 0.026(2) 0.046(3) -0.0017(18) -0.003(2) -0.0092(18)
C15 0.038(3) 0.043(3) 0.042(3) 0.003(2) -0.003(2) -0.014(2)
C16 0.063(4) 0.050(3) 0.050(3) 0.008(2) -0.025(3) -0.020(3)
C17 0.050(3) 0.055(3) 0.072(4) 0.018(3) -0.031(3) -0.027(3)
C18 0.033(3) 0.073(4) 0.076(4) 0.020(3) -0.003(3) -0.020(3)
C19 0.041(3) 0.053(3) 0.048(3) 0.001(2) 0.001(2) -0.009(2)
C20 0.031(2) 0.029(2) 0.028(2) 0.0043(17) -0.0020(18) -0.0123(18)
C21 0.027(2) 0.0244(19) 0.028(2) 0.0014(16) -0.0023(17) -0.0096(17)
N4 0.045(2) 0.0233(17) 0.0344(19) -0.0003(14) 0.0030(17) -0.0105(16)
N5 0.049(2) 0.0234(17) 0.0317(19) -0.0008(14) 0.0083(17) -0.0120(17)
N6 0.038(2) 0.0237(17) 0.0246(17) -0.0003(13) 0.0007(15) -0.0125(15)
C22 0.039(3) 0.0204(19) 0.031(2) 0.0007(16) -0.0041(19) -0.0150(18)
C23 0.039(3) 0.030(2) 0.026(2) 0.0013(17) 0.0038(18) -0.0129(19)
C24 0.033(2) 0.034(2) 0.0186(19) 0.0017(16) 0.0016(17) -0.0139(19)
C25 0.035(3) 0.027(2) 0.038(2) 0.0022(18) -0.005(2) -0.0131(19)
C26 0.047(3) 0.041(3) 0.053(3) 0.004(2) -0.011(2) -0.022(2)
C27 0.036(3) 0.065(3) 0.049(3) 0.008(2) -0.006(2) -0.020(3)
C28 0.031(3) 0.053(3) 0.049(3) 0.000(2) 0.001(2) 0.001(2)
C29 0.045(3) 0.034(2) 0.035(2) -0.0007(19) 0.006(2) -0.010(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.458(3) . ?
P1 O2 1.565(3) . ?
P1 O3 1.588(3) . ?
P1 C9 1.837(4) . ?
O2 C1 1.409(4) . ?
C1 C2 1.459(5) . ?
O3 C30 1.406(5) . ?
O3 C3 1.413(4) . ?
C3 C4 1.465(6) . ?
C30 C40 1.465(6) . ?
C9 C20 1.571(5) . ?
C9 C10 1.572(5) . ?
C9 P2 1.837(4) . ?
P2 O4 1.456(3) . ?
P2 O6 1.524(4) . ?
P2 O5 1.564(3) . ?
O5 C5 1.413(4) . ?
C5 C6 1.461(5) . ?
O6 C7 1.388(5) . ?
O6 C70 1.391(5) . ?
C7 C8 1.464(6) . ?
C70 C80 1.459(6) . ?
C10 C11 1.503(5) . ?
C11 C12 1.354(6) . ?
C11 N1 1.363(5) . ?
N1 N2 1.320(5) . ?
N2 N3 1.348(5) . ?
N3 C12 1.346(5) . ?
N3 C13 1.454(5) . ?
C13 C14 1.505(6) . ?
C14 C19 1.391(6) . ?
C14 C15 1.391(6) . ?
C15 C16 1.373(7) . ?
C16 C17 1.364(8) . ?
C17 C18 1.358(8) . ?
C18 C19 1.395(7) . ?
C20 C21 1.500(5) . ?
C21 N4 1.363(5) . ?
C21 C22 1.367(5) . ?
N4 N5 1.323(5) . ?
N5 N6 1.343(4) . ?
N6 C22 1.336(5) . ?
N6 C23 1.481(5) . ?
C23 C24 1.515(6) . ?
C24 C25 1.383(6) . ?
C24 C29 1.391(6) . ?
C25 C26 1.382(6) . ?
C26 C27 1.380(7) . ?
C27 C28 1.381(7) . ?
C28 C29 1.378(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 115.14(17) . . ?
O1 P1 O3 114.30(17) . . ?
O2 P1 O3 104.07(17) . . ?
O1 P1 C9 115.13(18) . . ?
O2 P1 C9 102.54(17) . . ?
O3 P1 C9 104.16(16) . . ?
C1 O2 P1 123.0(3) . . ?
O2 C1 C2 112.3(3) . . ?
C30 O3 C3 45.6(4) . . ?
C30 O3 P1 125.6(4) . . ?
C3 O3 P1 116.5(4) . . ?
O3 C3 C4 111.8(4) . . ?
O3 C30 C40 112.0(4) . . ?
C20 C9 C10 112.8(3) . . ?
C20 C9 P1 109.3(3) . . ?
C10 C9 P1 108.1(3) . . ?
C20 C9 P2 107.7(3) . . ?
C10 C9 P2 109.2(3) . . ?
P1 C9 P2 109.68(19) . . ?
O4 P2 O6 113.5(3) . . ?
O4 P2 O5 115.00(18) . . ?
O6 P2 O5 104.6(3) . . ?
O4 P2 C9 114.86(19) . . ?
O6 P2 C9 105.1(2) . . ?
O5 P2 C9 102.50(18) . . ?
C5 O5 P2 127.4(3) . . ?
O5 C5 C6 111.4(3) . . ?
C7 O6 C70 55.9(6) . . ?
C7 O6 P2 138.9(5) . . ?
C70 O6 P2 150.3(7) . . ?
O6 C7 C8 112.7(5) . . ?
O6 C70 C80 113.1(5) . . ?
C11 C10 C9 115.7(3) . . ?
C12 C11 N1 108.1(4) . . ?
C12 C11 C10 129.6(4) . . ?
N1 C11 C10 122.1(3) . . ?
N2 N1 C11 108.9(3) . . ?
N1 N2 N3 106.9(3) . . ?
C12 N3 N2 110.4(3) . . ?
C12 N3 C13 128.8(4) . . ?
N2 N3 C13 120.8(3) . . ?
N3 C12 C11 105.8(4) . . ?
N3 C13 C14 111.6(3) . . ?
C19 C14 C15 117.3(4) . . ?
C19 C14 C13 121.8(4) . . ?
C15 C14 C13 120.9(4) . . ?
C16 C15 C14 121.8(5) . . ?
C17 C16 C15 120.0(5) . . ?
C18 C17 C16 120.1(5) . . ?
C17 C18 C19 120.7(5) . . ?
C14 C19 C18 120.2(5) . . ?
C21 C20 C9 116.4(3) . . ?
N4 C21 C22 107.7(3) . . ?
N4 C21 C20 121.8(3) . . ?
C22 C21 C20 130.4(4) . . ?
N5 N4 C21 108.9(3) . . ?
N4 N5 N6 106.8(3) . . ?
C22 N6 N5 111.1(3) . . ?
C22 N6 C23 128.2(3) . . ?
N5 N6 C23 120.7(3) . . ?
N6 C22 C21 105.5(3) . . ?
N6 C23 C24 112.6(3) . . ?
C25 C24 C29 118.4(4) . . ?
C25 C24 C23 121.1(4) . . ?
C29 C24 C23 120.6(4) . . ?
C26 C25 C24 120.8(4) . . ?
C27 C26 C25 120.3(4) . . ?
C26 C27 C28 119.4(5) . . ?
C29 C28 C27 120.2(5) . . ?
C28 C29 C24 120.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 O2 C1 -20.6(5) . . . . ?
O3 P1 O2 C1 105.3(5) . . . . ?
C9 P1 O2 C1 -146.4(5) . . . . ?
P1 O2 C1 C2 158.5(4) . . . . ?
O1 P1 O3 C30 2.6(5) . . . . ?
O2 P1 O3 C30 -123.8(5) . . . . ?
C9 P1 O3 C30 129.1(4) . . . . ?
O1 P1 O3 C3 55.5(5) . . . . ?
O2 P1 O3 C3 -70.9(4) . . . . ?
C9 P1 O3 C3 -178.0(4) . . . . ?
C30 O3 C3 C4 -11.9(7) . . . . ?
P1 O3 C3 C4 -127.0(6) . . . . ?
C3 O3 C30 C40 5.4(7) . . . . ?
P1 O3 C30 C40 99.2(8) . . . . ?
O1 P1 C9 C20 -163.5(2) . . . . ?
O2 P1 C9 C20 -37.7(3) . . . . ?
O3 P1 C9 C20 70.5(3) . . . . ?
O1 P1 C9 C10 -40.4(3) . . . . ?
O2 P1 C9 C10 85.4(3) . . . . ?
O3 P1 C9 C10 -166.4(3) . . . . ?
O1 P1 C9 P2 78.6(2) . . . . ?
O2 P1 C9 P2 -155.62(19) . . . . ?
O3 P1 C9 P2 -47.4(2) . . . . ?
C20 C9 P2 O4 -32.9(3) . . . . ?
C10 C9 P2 O4 -155.7(2) . . . . ?
P1 C9 P2 O4 86.0(2) . . . . ?
C20 C9 P2 O6 -158.4(3) . . . . ?
C10 C9 P2 O6 78.8(3) . . . . ?
P1 C9 P2 O6 -39.5(3) . . . . ?
C20 C9 P2 O5 92.6(3) . . . . ?
C10 C9 P2 O5 -30.3(3) . . . . ?
P1 C9 P2 O5 -148.6(2) . . . . ?
O4 P2 O5 C5 -24.1(5) . . . . ?
O6 P2 O5 C5 101.1(5) . . . . ?
C9 P2 O5 C5 -149.4(4) . . . . ?
P2 O5 C5 C6 158.5(4) . . . . ?
O4 P2 O6 C7 21.8(10) . . . . ?
O5 P2 O6 C7 -104.3(10) . . . . ?
C9 P2 O6 C7 148.1(10) . . . . ?
O4 P2 O6 C70 128.6(13) . . . . ?
O5 P2 O6 C70 2.5(13) . . . . ?
C9 P2 O6 C70 -105.1(13) . . . . ?
C70 O6 C7 C8 31(2) . . . . ?
P2 O6 C7 C8 175.7(16) . . . . ?
C7 O6 C70 C80 -16.1(17) . . . . ?
P2 O6 C70 C80 -146.6(14) . . . . ?
C20 C9 C10 C11 57.8(4) . . . . ?
P1 C9 C10 C11 -63.2(4) . . . . ?
P2 C9 C10 C11 177.5(3) . . . . ?
C9 C10 C11 C12 -83.7(5) . . . . ?
C9 C10 C11 N1 102.6(4) . . . . ?
C12 C11 N1 N2 1.2(5) . . . . ?
C10 C11 N1 N2 176.0(3) . . . . ?
C11 N1 N2 N3 -1.2(4) . . . . ?
N1 N2 N3 C12 0.8(4) . . . . ?
N1 N2 N3 C13 -179.1(3) . . . . ?
N2 N3 C12 C11 0.0(4) . . . . ?
C13 N3 C12 C11 179.8(4) . . . . ?
N1 C11 C12 N3 -0.7(4) . . . . ?
C10 C11 C12 N3 -175.0(4) . . . . ?
C12 N3 C13 C14 83.4(5) . . . . ?
N2 N3 C13 C14 -96.7(4) . . . . ?
N3 C13 C14 C19 105.8(5) . . . . ?
N3 C13 C14 C15 -72.3(5) . . . . ?
C19 C14 C15 C16 -0.9(7) . . . . ?
C13 C14 C15 C16 177.3(4) . . . . ?
C14 C15 C16 C17 -0.6(7) . . . . ?
C15 C16 C17 C18 1.6(8) . . . . ?
C16 C17 C18 C19 -1.2(8) . . . . ?
C15 C14 C19 C18 1.3(7) . . . . ?
C13 C14 C19 C18 -176.8(4) . . . . ?
C17 C18 C19 C14 -0.4(8) . . . . ?
C10 C9 C20 C21 62.9(4) . . . . ?
P1 C9 C20 C21 -176.8(3) . . . . ?
P2 C9 C20 C21 -57.7(4) . . . . ?
C9 C20 C21 N4 -85.5(5) . . . . ?
C9 C20 C21 C22 97.9(5) . . . . ?
C22 C21 N4 N5 -0.1(5) . . . . ?
C20 C21 N4 N5 -177.4(4) . . . . ?
C21 N4 N5 N6 0.0(5) . . . . ?
N4 N5 N6 C22 0.1(5) . . . . ?
N4 N5 N6 C23 179.2(4) . . . . ?
N5 N6 C22 C21 -0.2(5) . . . . ?
C23 N6 C22 C21 -179.2(4) . . . . ?
N4 C21 C22 N6 0.2(5) . . . . ?
C20 C21 C22 N6 177.1(4) . . . . ?
C22 N6 C23 C24 -111.2(5) . . . . ?
N5 N6 C23 C24 69.8(5) . . . . ?
N6 C23 C24 C25 -74.2(5) . . . . ?
N6 C23 C24 C29 106.3(4) . . . . ?
C29 C24 C25 C26 0.4(6) . . . . ?
C23 C24 C25 C26 -179.1(4) . . . . ?
C24 C25 C26 C27 -0.3(7) . . . . ?
C25 C26 C27 C28 0.3(7) . . . . ?
C26 C27 C28 C29 -0.4(7) . . . . ?
C27 C28 C29 C24 0.4(7) . . . . ?
C25 C24 C29 C28 -0.4(6) . . . . ?
C23 C24 C29 C28 179.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.076