# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Leroux, Frederic'
_publ_contact_author_email       frederic.leroux@unistra.fr

_publ_section_title              
;
[1,2,3]Triazolo[1,5-a]pyridyl Phosphines Reflecting
the Influence of Phosphorus Lone Pair Orientation on Spectroscopic Properties
;
loop_
_publ_author_name
R.Ballesteros-Garrido
L.Bonnafoux
F.Blanco
R.Ballesteros
;
F.Leroux
;
B.Abarca
F.Colobert
I.Alkorta
J.Elguero

# Attachment '- 4a.cif'

data_colo36
_database_code_depnum_ccdc_archive 'CCDC 799866'
#TrackingRef '- 4a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N3 P'
_chemical_formula_sum            'C19 H16 N3 P'
_chemical_formula_weight         317.32

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'
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                   11.7432(4)
_cell_length_b                   12.4966(4)
_cell_length_c                   13.3411(5)
_cell_angle_alpha                79.341(2)
_cell_angle_beta                 66.710(2)
_cell_angle_gamma                65.127(2)
_cell_volume                     1631.06(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9832
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.171
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18652
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         27.49
_reflns_number_total             7470
_reflns_number_gt                5023
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_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^)+(0.0966P)^2^+0.0000P] 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         7470
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
C1 C 0.6124(2) -0.3827(2) 1.3422(2) 0.0395(6) Uani 1 1 d . . .
C2 C 0.6151(2) -0.2723(2) 1.30640(19) 0.0312(5) Uani 1 1 d . . .
C3 C 0.5773(2) -0.1859(2) 1.2284(2) 0.0372(6) Uani 1 1 d . . .
H3 H 0.5443 -0.2003 1.1799 0.045 Uiso 1 1 calc R . .
C4 C 0.5894(3) -0.0818(2) 1.2242(2) 0.0404(6) Uani 1 1 d . . .
H4 H 0.5608 -0.0216 1.1742 0.049 Uiso 1 1 calc R . .
C5 C 0.6439(2) -0.0609(2) 1.2930(2) 0.0353(6) Uani 1 1 d . . .
H5 H 0.6529 0.0123 1.2868 0.042 Uiso 1 1 calc R . .
C6 C 0.6837(2) -0.1435(2) 1.36790(19) 0.0300(5) Uani 1 1 d . . .
C7 C 0.5641(3) -0.4536(3) 1.3018(3) 0.0577(8) Uani 1 1 d . . .
H7A H 0.6373 -0.4997 1.2393 0.087 Uiso 1 1 calc R . .
H7B H 0.4884 -0.4005 1.2794 0.087 Uiso 1 1 calc R . .
H7C H 0.5351 -0.5071 1.3603 0.087 Uiso 1 1 calc R . .
C8 C 0.9138(2) -0.23732(19) 1.43027(19) 0.0294(5) Uani 1 1 d . . .
C9 C 0.9791(2) -0.30585(19) 1.33780(19) 0.0313(5) Uani 1 1 d . . .
H9 H 0.9366 -0.2926 1.2865 0.038 Uiso 1 1 calc R . .
C10 C 1.1066(2) -0.39377(19) 1.3202(2) 0.0339(6) Uani 1 1 d . . .
H10 H 1.1507 -0.4403 1.2569 0.041 Uiso 1 1 calc R . .
C11 C 1.1696(2) -0.4140(2) 1.3942(2) 0.0350(6) Uani 1 1 d . . .
H11 H 1.2555 -0.4757 1.3828 0.042 Uiso 1 1 calc R . .
C12 C 1.1071(2) -0.3442(2) 1.4846(2) 0.0378(6) Uani 1 1 d . . .
H12 H 1.1511 -0.3559 1.5344 0.045 Uiso 1 1 calc R . .
C13 C 0.9803(2) -0.2571(2) 1.5022(2) 0.0360(6) Uani 1 1 d . . .
H13 H 0.9376 -0.2097 1.5649 0.043 Uiso 1 1 calc R . .
C14 C 0.7714(2) 0.0111(2) 1.41206(19) 0.0316(5) Uani 1 1 d . . .
C15 C 0.8758(3) 0.0154(2) 1.3173(2) 0.0395(6) Uani 1 1 d . . .
H15 H 0.9396 -0.0555 1.2801 0.047 Uiso 1 1 calc R . .
C16 C 0.8890(3) 0.1216(2) 1.2756(2) 0.0450(7) Uani 1 1 d . . .
H16 H 0.9607 0.1237 1.2100 0.054 Uiso 1 1 calc R . .
C17 C 0.7963(3) 0.2244(2) 1.3308(2) 0.0445(7) Uani 1 1 d . . .
H17 H 0.8041 0.2976 1.3025 0.053 Uiso 1 1 calc R . .
C18 C 0.6937(3) 0.2215(2) 1.4256(2) 0.0464(7) Uani 1 1 d . . .
H18 H 0.6312 0.2924 1.4632 0.056 Uiso 1 1 calc R . .
C19 C 0.6804(2) 0.1150(2) 1.4672(2) 0.0385(6) Uani 1 1 d . . .
H19 H 0.6092 0.1133 1.5333 0.046 Uiso 1 1 calc R . .
C20 C 0.2010(2) 0.34932(19) 1.1430(2) 0.0311(5) Uani 1 1 d . . .
C21 C 0.3104(2) 0.32443(18) 1.17410(18) 0.0278(5) Uani 1 1 d . . .
C22 C 0.3364(2) 0.30972(19) 1.27189(19) 0.0324(5) Uani 1 1 d . . .
H22 H 0.2663 0.3176 1.3410 0.039 Uiso 1 1 calc R . .
C23 C 0.4637(2) 0.2842(2) 1.2643(2) 0.0350(6) Uani 1 1 d . . .
H23 H 0.4830 0.2727 1.3292 0.042 Uiso 1 1 calc R . .
C24 C 0.5687(2) 0.2742(2) 1.16134(19) 0.0333(6) Uani 1 1 d . . .
H24 H 0.6565 0.2574 1.1590 0.040 Uiso 1 1 calc R . .
C25 C 0.5470(2) 0.28808(18) 1.06581(19) 0.0275(5) Uani 1 1 d . . .
C26 C 0.0580(3) 0.3755(2) 1.2121(2) 0.0430(6) Uani 1 1 d . . .
H26A H 0.0003 0.4385 1.1772 0.065 Uiso 1 1 calc R . .
H26B H 0.0402 0.4010 1.2839 0.065 Uiso 1 1 calc R . .
H26C H 0.0390 0.3044 1.2209 0.065 Uiso 1 1 calc R . .
C27 C 0.8137(2) 0.26614(19) 0.95121(18) 0.0295(5) Uani 1 1 d . . .
C28 C 0.8276(3) 0.3614(2) 0.9784(2) 0.0389(6) Uani 1 1 d . . .
H28 H 0.7554 0.4364 0.9895 0.047 Uiso 1 1 calc R . .
C29 C 0.9449(3) 0.3482(2) 0.9895(2) 0.0463(7) Uani 1 1 d . . .
H29 H 0.9522 0.4135 1.0094 0.056 Uiso 1 1 calc R . .
C30 C 1.0513(3) 0.2405(3) 0.9717(2) 0.0471(7) Uani 1 1 d . . .
H30 H 1.1327 0.2320 0.9776 0.057 Uiso 1 1 calc R . .
C31 C 1.0393(3) 0.1452(2) 0.9452(2) 0.0414(6) Uani 1 1 d . . .
H31 H 1.1124 0.0708 0.9336 0.050 Uiso 1 1 calc R . .
C32 C 0.9210(2) 0.1571(2) 0.93543(19) 0.0335(5) Uani 1 1 d . . .
H32 H 0.9133 0.0907 0.9179 0.040 Uiso 1 1 calc R . .
C33 C 0.6950(2) 0.16067(19) 0.86868(18) 0.0275(5) Uani 1 1 d . . .
C34 C 0.7543(2) 0.1502(2) 0.75569(19) 0.0333(5) Uani 1 1 d . . .
H34 H 0.7767 0.2126 0.7118 0.040 Uiso 1 1 calc R . .
C35 C 0.7809(3) 0.0491(2) 0.7067(2) 0.0399(6) Uani 1 1 d . . .
H35 H 0.8224 0.0422 0.6297 0.048 Uiso 1 1 calc R . .
C36 C 0.7470(3) -0.0413(2) 0.7698(2) 0.0390(6) Uani 1 1 d . . .
H36 H 0.7643 -0.1099 0.7361 0.047 Uiso 1 1 calc R . .
C37 C 0.6880(2) -0.0322(2) 0.8819(2) 0.0375(6) Uani 1 1 d . . .
H37 H 0.6644 -0.0944 0.9252 0.045 Uiso 1 1 calc R . .
C38 C 0.6632(2) 0.0678(2) 0.9310(2) 0.0334(5) Uani 1 1 d . . .
H38 H 0.6241 0.0730 1.0083 0.040 Uiso 1 1 calc R . .
N1 N 0.6568(2) -0.41861(18) 1.42655(19) 0.0437(6) Uani 1 1 d . . .
N2 N 0.6899(2) -0.33688(17) 1.44728(18) 0.0393(5) Uani 1 1 d . . .
N3 N 0.66415(18) -0.24727(16) 1.37373(15) 0.0303(4) Uani 1 1 d . . .
N4 N 0.24543(19) 0.34829(16) 1.03269(16) 0.0325(5) Uani 1 1 d . . .
N5 N 0.37644(19) 0.32475(16) 0.99009(16) 0.0308(4) Uani 1 1 d . . .
N6 N 0.41582(18) 0.31090(15) 1.07653(15) 0.0269(4) Uani 1 1 d . . .
P1 P 0.74245(6) -0.12461(5) 1.46897(5) 0.03111(18) Uani 1 1 d . . .
P2 P 0.66007(6) 0.29830(5) 0.92617(5) 0.02817(17) 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
C1 0.0320(13) 0.0374(14) 0.0472(16) 0.0011(11) -0.0172(13) -0.0097(11)
C2 0.0229(12) 0.0387(13) 0.0291(13) -0.0024(10) -0.0090(10) -0.0088(10)
C3 0.0315(13) 0.0546(16) 0.0282(13) 0.0027(11) -0.0139(11) -0.0174(12)
C4 0.0389(14) 0.0525(16) 0.0349(15) 0.0162(12) -0.0216(12) -0.0213(12)
C5 0.0326(13) 0.0400(14) 0.0355(14) 0.0088(11) -0.0154(12) -0.0170(11)
C6 0.0221(11) 0.0355(13) 0.0282(13) -0.0008(10) -0.0074(10) -0.0086(9)
C7 0.064(2) 0.0486(17) 0.077(2) 0.0013(15) -0.0406(19) -0.0233(15)
C8 0.0305(12) 0.0314(12) 0.0255(12) 0.0015(9) -0.0106(10) -0.0114(10)
C9 0.0327(13) 0.0324(12) 0.0303(13) -0.0006(10) -0.0147(11) -0.0106(10)
C10 0.0328(13) 0.0298(12) 0.0351(14) -0.0073(10) -0.0080(11) -0.0095(10)
C11 0.0293(13) 0.0311(12) 0.0398(15) 0.0007(10) -0.0133(11) -0.0070(10)
C12 0.0366(14) 0.0439(14) 0.0358(14) 0.0005(11) -0.0201(12) -0.0120(11)
C13 0.0355(14) 0.0417(14) 0.0298(13) -0.0052(10) -0.0142(11) -0.0097(11)
C14 0.0263(12) 0.0351(13) 0.0304(13) -0.0042(10) -0.0111(11) -0.0069(10)
C15 0.0333(14) 0.0385(14) 0.0388(15) -0.0088(11) -0.0055(12) -0.0104(11)
C16 0.0381(15) 0.0454(16) 0.0487(17) -0.0009(13) -0.0099(13) -0.0188(12)
C17 0.0404(15) 0.0368(14) 0.063(2) 0.0016(13) -0.0257(15) -0.0151(12)
C18 0.0365(15) 0.0357(14) 0.0597(19) -0.0114(13) -0.0150(15) -0.0050(11)
C19 0.0303(13) 0.0401(14) 0.0368(15) -0.0086(11) -0.0091(12) -0.0056(11)
C20 0.0335(13) 0.0293(12) 0.0337(14) -0.0007(10) -0.0122(11) -0.0148(10)
C21 0.0310(12) 0.0218(11) 0.0282(12) -0.0016(9) -0.0075(11) -0.0104(9)
C22 0.0368(14) 0.0308(12) 0.0256(13) -0.0017(10) -0.0081(11) -0.0118(10)
C23 0.0397(14) 0.0373(13) 0.0274(13) 0.0002(10) -0.0146(12) -0.0121(11)
C24 0.0328(13) 0.0363(13) 0.0324(14) -0.0032(10) -0.0152(11) -0.0103(10)
C25 0.0278(12) 0.0244(11) 0.0310(13) -0.0043(9) -0.0112(10) -0.0086(9)
C26 0.0355(14) 0.0497(15) 0.0439(16) 0.0017(12) -0.0117(13) -0.0198(12)
C27 0.0321(12) 0.0327(12) 0.0253(12) -0.0005(9) -0.0082(10) -0.0161(10)
C28 0.0475(16) 0.0343(13) 0.0437(16) 0.0013(11) -0.0206(13) -0.0207(11)
C29 0.0613(19) 0.0518(16) 0.0471(17) 0.0038(13) -0.0281(15) -0.0350(14)
C30 0.0435(16) 0.0662(19) 0.0463(17) 0.0072(14) -0.0225(14) -0.0319(14)
C31 0.0335(14) 0.0472(15) 0.0431(16) 0.0015(12) -0.0166(13) -0.0134(11)
C32 0.0326(13) 0.0367(13) 0.0333(14) -0.0021(10) -0.0096(11) -0.0168(10)
C33 0.0258(12) 0.0317(12) 0.0266(12) -0.0011(9) -0.0109(10) -0.0110(9)
C34 0.0342(13) 0.0394(13) 0.0279(13) -0.0008(10) -0.0089(11) -0.0177(11)
C35 0.0373(14) 0.0476(15) 0.0325(14) -0.0141(12) -0.0071(12) -0.0139(12)
C36 0.0385(14) 0.0352(13) 0.0448(16) -0.0122(11) -0.0146(13) -0.0113(11)
C37 0.0383(14) 0.0290(12) 0.0449(16) -0.0008(11) -0.0138(13) -0.0136(10)
C38 0.0392(14) 0.0329(13) 0.0263(13) -0.0006(10) -0.0093(11) -0.0144(10)
N1 0.0413(13) 0.0394(12) 0.0567(15) 0.0087(10) -0.0270(12) -0.0163(10)
N2 0.0393(12) 0.0377(12) 0.0435(13) 0.0114(10) -0.0231(11) -0.0145(9)
N3 0.0263(10) 0.0340(10) 0.0296(11) 0.0048(8) -0.0136(9) -0.0096(8)
N4 0.0313(11) 0.0334(11) 0.0364(12) -0.0013(9) -0.0135(10) -0.0142(8)
N5 0.0323(11) 0.0337(10) 0.0305(11) -0.0029(8) -0.0138(9) -0.0131(8)
N6 0.0300(10) 0.0268(9) 0.0266(10) -0.0020(8) -0.0117(9) -0.0112(8)
P1 0.0272(3) 0.0355(3) 0.0261(3) -0.0014(3) -0.0091(3) -0.0079(3)
P2 0.0303(3) 0.0282(3) 0.0269(3) -0.0013(2) -0.0105(3) -0.0116(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
C1 N1 1.350(3) . ?
C1 C2 1.383(3) . ?
C1 C7 1.495(4) . ?
C2 N3 1.379(3) . ?
C2 C3 1.411(3) . ?
C3 C4 1.356(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.365(3) . ?
C5 H5 0.9500 . ?
C6 N3 1.393(3) . ?
C6 P1 1.828(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.391(3) . ?
C8 C13 1.391(3) . ?
C8 P1 1.834(2) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.382(3) . ?
C14 C19 1.391(3) . ?
C14 P1 1.836(3) . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.366(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 N4 1.354(3) . ?
C20 C21 1.399(3) . ?
C20 C26 1.484(4) . ?
C21 N6 1.374(3) . ?
C21 C22 1.417(3) . ?
C22 C23 1.356(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.421(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.363(3) . ?
C24 H24 0.9500 . ?
C25 N6 1.396(3) . ?
C25 P2 1.830(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.393(3) . ?
C27 C28 1.396(3) . ?
C27 P2 1.828(2) . ?
C28 C29 1.381(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.377(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.379(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.390(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C38 1.393(3) . ?
C33 C34 1.393(3) . ?
C33 P2 1.833(2) . ?
C34 C35 1.390(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.380(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.387(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
N1 N2 1.339(3) . ?
N2 N3 1.361(3) . ?
N4 N5 1.329(3) . ?
N5 N6 1.362(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
N1 C1 C2 108.7(2) . . ?
N1 C1 C7 122.9(2) . . ?
C2 C1 C7 128.3(2) . . ?
N3 C2 C1 104.09(19) . . ?
N3 C2 C3 118.3(2) . . ?
C1 C2 C3 137.5(2) . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 N3 115.7(2) . . ?
C5 C6 P1 126.41(19) . . ?
N3 C6 P1 117.60(16) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.4(2) . . ?
C9 C8 P1 125.26(17) . . ?
C13 C8 P1 116.27(18) . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
C15 C14 C19 119.0(2) . . ?
C15 C14 P1 123.71(18) . . ?
C19 C14 P1 117.30(19) . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.0(2) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
N4 C20 C21 108.1(2) . . ?
N4 C20 C26 122.5(2) . . ?
C21 C20 C26 129.3(2) . . ?
N6 C21 C20 103.66(19) . . ?
N6 C21 C22 118.2(2) . . ?
C20 C21 C22 138.1(2) . . ?
C23 C22 C21 118.4(2) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C22 C23 C24 121.3(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C25 C24 C23 121.8(2) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 N6 115.4(2) . . ?
C24 C25 P2 129.04(18) . . ?
N6 C25 P2 115.11(15) . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 118.4(2) . . ?
C32 C27 P2 124.74(18) . . ?
C28 C27 P2 116.55(17) . . ?
C29 C28 C27 120.9(2) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C30 C29 C28 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 119.7(2) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C32 120.5(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C31 C32 C27 120.2(2) . . ?
C31 C32 H32 119.9 . . ?
C27 C32 H32 119.9 . . ?
C38 C33 C34 118.5(2) . . ?
C38 C33 P2 123.89(18) . . ?
C34 C33 P2 117.61(17) . . ?
C35 C34 C33 120.5(2) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C34 120.1(2) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C37 C36 C35 120.1(2) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C36 C37 C38 119.9(2) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C37 C38 C33 120.9(2) . . ?
C37 C38 H38 119.5 . . ?
C33 C38 H38 119.5 . . ?
N2 N1 C1 110.3(2) . . ?
N1 N2 N3 105.79(19) . . ?
N2 N3 C2 111.09(19) . . ?
N2 N3 C6 124.42(19) . . ?
C2 N3 C6 124.48(18) . . ?
N5 N4 C20 110.82(19) . . ?
N4 N5 N6 105.73(18) . . ?
N5 N6 C21 111.64(17) . . ?
N5 N6 C25 123.53(19) . . ?
C21 N6 C25 124.82(19) . . ?
C6 P1 C8 102.22(10) . . ?
C6 P1 C14 98.57(10) . . ?
C8 P1 C14 102.27(11) . . ?
C27 P2 C25 100.09(10) . . ?
C27 P2 C33 102.77(10) . . ?
C25 P2 C33 101.79(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
N1 C1 C2 N3 0.5(3) . . . . ?
C7 C1 C2 N3 177.9(3) . . . . ?
N1 C1 C2 C3 -176.1(3) . . . . ?
C7 C1 C2 C3 1.3(5) . . . . ?
N3 C2 C3 C4 -0.9(3) . . . . ?
C1 C2 C3 C4 175.4(3) . . . . ?
C2 C3 C4 C5 2.7(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 N3 -1.5(3) . . . . ?
C4 C5 C6 P1 -174.67(19) . . . . ?
C13 C8 C9 C10 1.6(4) . . . . ?
P1 C8 C9 C10 -176.15(18) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -1.9(4) . . . . ?
C10 C11 C12 C13 2.0(4) . . . . ?
C11 C12 C13 C8 -0.4(4) . . . . ?
C9 C8 C13 C12 -1.4(4) . . . . ?
P1 C8 C13 C12 176.5(2) . . . . ?
C19 C14 C15 C16 -1.5(4) . . . . ?
P1 C14 C15 C16 177.03(19) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C15 C14 C19 C18 1.3(4) . . . . ?
P1 C14 C19 C18 -177.26(19) . . . . ?
C17 C18 C19 C14 -0.3(4) . . . . ?
N4 C20 C21 N6 0.5(2) . . . . ?
C26 C20 C21 N6 -178.4(2) . . . . ?
N4 C20 C21 C22 -178.4(2) . . . . ?
C26 C20 C21 C22 2.6(5) . . . . ?
N6 C21 C22 C23 0.6(3) . . . . ?
C20 C21 C22 C23 179.5(3) . . . . ?
C21 C22 C23 C24 1.1(3) . . . . ?
C22 C23 C24 C25 -1.0(4) . . . . ?
C23 C24 C25 N6 -0.9(3) . . . . ?
C23 C24 C25 P2 171.12(18) . . . . ?
C32 C27 C28 C29 0.0(4) . . . . ?
P2 C27 C28 C29 -174.3(2) . . . . ?
C27 C28 C29 C30 1.2(4) . . . . ?
C28 C29 C30 C31 -1.5(4) . . . . ?
C29 C30 C31 C32 0.6(4) . . . . ?
C30 C31 C32 C27 0.7(4) . . . . ?
C28 C27 C32 C31 -0.9(4) . . . . ?
P2 C27 C32 C31 172.85(19) . . . . ?
C38 C33 C34 C35 0.0(3) . . . . ?
P2 C33 C34 C35 -178.66(18) . . . . ?
C33 C34 C35 C36 0.9(4) . . . . ?
C34 C35 C36 C37 -0.7(4) . . . . ?
C35 C36 C37 C38 -0.2(4) . . . . ?
C36 C37 C38 C33 1.1(4) . . . . ?
C34 C33 C38 C37 -1.0(3) . . . . ?
P2 C33 C38 C37 177.59(18) . . . . ?
C2 C1 N1 N2 -0.6(3) . . . . ?
C7 C1 N1 N2 -178.2(3) . . . . ?
C1 N1 N2 N3 0.4(3) . . . . ?
N1 N2 N3 C2 -0.1(3) . . . . ?
N1 N2 N3 C6 179.3(2) . . . . ?
C1 C2 N3 N2 -0.2(3) . . . . ?
C3 C2 N3 N2 177.2(2) . . . . ?
C1 C2 N3 C6 -179.7(2) . . . . ?
C3 C2 N3 C6 -2.3(3) . . . . ?
C5 C6 N3 N2 -176.0(2) . . . . ?
P1 C6 N3 N2 -2.2(3) . . . . ?
C5 C6 N3 C2 3.4(3) . . . . ?
P1 C6 N3 C2 177.21(17) . . . . ?
C21 C20 N4 N5 -0.2(3) . . . . ?
C26 C20 N4 N5 178.8(2) . . . . ?
C20 N4 N5 N6 -0.2(2) . . . . ?
N4 N5 N6 C21 0.6(2) . . . . ?
N4 N5 N6 C25 -178.23(18) . . . . ?
C20 C21 N6 N5 -0.7(2) . . . . ?
C22 C21 N6 N5 178.53(18) . . . . ?
C20 C21 N6 C25 178.11(19) . . . . ?
C22 C21 N6 C25 -2.7(3) . . . . ?
C24 C25 N6 N5 -178.59(19) . . . . ?
P2 C25 N6 N5 8.3(3) . . . . ?
C24 C25 N6 C21 2.7(3) . . . . ?
P2 C25 N6 C21 -170.40(16) . . . . ?
C5 C6 P1 C8 -118.9(2) . . . . ?
N3 C6 P1 C8 68.07(19) . . . . ?
C5 C6 P1 C14 -14.2(2) . . . . ?
N3 C6 P1 C14 172.70(17) . . . . ?
C9 C8 P1 C6 6.7(2) . . . . ?
C13 C8 P1 C6 -171.11(19) . . . . ?
C9 C8 P1 C14 -95.1(2) . . . . ?
C13 C8 P1 C14 87.2(2) . . . . ?
C15 C14 P1 C6 -71.7(2) . . . . ?
C19 C14 P1 C6 106.78(19) . . . . ?
C15 C14 P1 C8 32.9(2) . . . . ?
C19 C14 P1 C8 -148.64(18) . . . . ?
C32 C27 P2 C25 100.3(2) . . . . ?
C28 C27 P2 C25 -85.8(2) . . . . ?
C32 C27 P2 C33 -4.3(2) . . . . ?
C28 C27 P2 C33 169.56(19) . . . . ?
C24 C25 P2 C27 6.8(2) . . . . ?
N6 C25 P2 C27 178.79(16) . . . . ?
C24 C25 P2 C33 112.2(2) . . . . ?
N6 C25 P2 C33 -75.76(17) . . . . ?
C38 C33 P2 C27 90.6(2) . . . . ?
C34 C33 P2 C27 -90.79(19) . . . . ?
C38 C33 P2 C25 -12.7(2) . . . . ?
C34 C33 P2 C25 165.86(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.103

# Attachment '- 4b.cif'

data_colo34
_database_code_depnum_ccdc_archive 'CCDC 799867'
#TrackingRef '- 4b.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N3 P'
_chemical_formula_sum            'C18 H14 N3 P'
_chemical_formula_weight         303.29

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'
P P 0.1023 0.0942 '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 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.4104(5)
_cell_length_b                   16.0595(10)
_cell_length_c                   10.0214(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.277(3)
_cell_angle_gamma                90.00
_cell_volume                     1494.69(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8238
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.183
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10729
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3414
_reflns_number_gt                2517
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_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^)+(0.1011P)^2^+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.079(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3414
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1774(2) -0.02780(15) 0.9538(2) 0.0363(6) Uani 1 1 d . . .
H1 H 0.1360 -0.0660 1.0090 0.044 Uiso 1 1 calc R . .
C2 C 0.3027(2) -0.04111(14) 0.90204(19) 0.0294(5) Uani 1 1 d . . .
C3 C 0.4100(2) -0.10257(14) 0.9036(2) 0.0327(5) Uani 1 1 d . . .
H3 H 0.4035 -0.1539 0.9494 0.039 Uiso 1 1 calc R . .
C4 C 0.5228(2) -0.08696(14) 0.8382(2) 0.0330(5) Uani 1 1 d . . .
H4 H 0.5963 -0.1276 0.8393 0.040 Uiso 1 1 calc R . .
C5 C 0.5328(2) -0.01094(13) 0.7683(2) 0.0287(5) Uani 1 1 d . . .
H5 H 0.6136 -0.0017 0.7243 0.034 Uiso 1 1 calc R . .
C6 C 0.4300(2) 0.04907(13) 0.7624(2) 0.0261(5) Uani 1 1 d . . .
C7 C 0.6009(2) 0.15623(12) 0.6324(2) 0.0256(5) Uani 1 1 d . . .
C8 C 0.7198(2) 0.16825(14) 0.7332(2) 0.0342(5) Uani 1 1 d . . .
H8 H 0.7061 0.1715 0.8249 0.041 Uiso 1 1 calc R . .
C9 C 0.8573(3) 0.17556(16) 0.7023(3) 0.0414(6) Uani 1 1 d . . .
H9 H 0.9374 0.1822 0.7724 0.050 Uiso 1 1 calc R . .
C10 C 0.8775(3) 0.17320(15) 0.5689(3) 0.0395(6) Uani 1 1 d . . .
H10 H 0.9716 0.1788 0.5471 0.047 Uiso 1 1 calc R . .
C11 C 0.7620(3) 0.16281(14) 0.4679(3) 0.0363(6) Uani 1 1 d . . .
H11 H 0.7766 0.1618 0.3762 0.044 Uiso 1 1 calc R . .
C12 C 0.6230(2) 0.15367(13) 0.4983(2) 0.0302(5) Uani 1 1 d . . .
H12 H 0.5438 0.1457 0.4277 0.036 Uiso 1 1 calc R . .
C13 C 0.2975(2) 0.13885(13) 0.5317(2) 0.0262(5) Uani 1 1 d . . .
C14 C 0.2260(2) 0.06419(14) 0.4937(2) 0.0319(5) Uani 1 1 d . . .
H14 H 0.2431 0.0168 0.5507 0.038 Uiso 1 1 calc R . .
C15 C 0.1303(3) 0.05872(15) 0.3730(2) 0.0381(6) Uani 1 1 d . . .
H15 H 0.0809 0.0080 0.3487 0.046 Uiso 1 1 calc R . .
C16 C 0.1068(2) 0.12726(16) 0.2881(2) 0.0383(6) Uani 1 1 d . . .
H16 H 0.0427 0.1232 0.2048 0.046 Uiso 1 1 calc R . .
C17 C 0.1764(2) 0.20137(16) 0.3246(2) 0.0382(6) Uani 1 1 d . . .
H17 H 0.1610 0.2482 0.2660 0.046 Uiso 1 1 calc R . .
C18 C 0.2688(2) 0.20751(14) 0.4464(2) 0.0326(5) Uani 1 1 d . . .
H18 H 0.3134 0.2594 0.4724 0.039 Uiso 1 1 calc R . .
N1 N 0.1226(2) 0.04725(13) 0.9146(2) 0.0398(5) Uani 1 1 d . . .
N2 N 0.20675(19) 0.08462(13) 0.83903(19) 0.0357(5) Uani 1 1 d . . .
N3 N 0.31655(18) 0.03144(11) 0.83112(17) 0.0268(4) Uani 1 1 d . . .
P1 P 0.42520(6) 0.15362(4) 0.68810(5) 0.0270(2) 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
C1 0.0326(12) 0.0424(15) 0.0353(12) 0.0050(11) 0.0102(10) -0.0060(11)
C2 0.0324(11) 0.0314(12) 0.0247(10) 0.0001(9) 0.0051(9) -0.0070(9)
C3 0.0408(13) 0.0295(12) 0.0275(11) 0.0009(9) 0.0049(10) -0.0031(10)
C4 0.0370(12) 0.0337(13) 0.0284(11) 0.0002(9) 0.0058(9) 0.0088(10)
C5 0.0289(11) 0.0305(12) 0.0277(10) -0.0016(9) 0.0078(9) 0.0007(9)
C6 0.0264(10) 0.0297(12) 0.0233(10) -0.0020(8) 0.0073(9) -0.0034(9)
C7 0.0287(11) 0.0199(10) 0.0294(11) 0.0000(8) 0.0080(9) -0.0020(8)
C8 0.0336(12) 0.0368(13) 0.0329(12) 0.0008(10) 0.0075(10) -0.0065(10)
C9 0.0287(12) 0.0466(16) 0.0477(14) 0.0002(12) 0.0022(11) -0.0087(11)
C10 0.0284(12) 0.0382(14) 0.0550(15) 0.0019(12) 0.0160(11) -0.0046(10)
C11 0.0379(13) 0.0349(13) 0.0408(13) 0.0009(10) 0.0205(11) 0.0030(10)
C12 0.0305(11) 0.0296(12) 0.0314(11) -0.0010(9) 0.0076(9) -0.0011(9)
C13 0.0216(10) 0.0259(11) 0.0329(11) 0.0013(8) 0.0099(9) 0.0029(8)
C14 0.0330(12) 0.0250(12) 0.0385(12) 0.0004(9) 0.0084(10) 0.0020(9)
C15 0.0357(12) 0.0332(14) 0.0448(14) -0.0046(10) 0.0048(11) -0.0033(10)
C16 0.0295(11) 0.0477(15) 0.0366(13) 0.0009(11) 0.0016(10) 0.0004(11)
C17 0.0293(12) 0.0433(15) 0.0422(13) 0.0101(11) 0.0063(10) 0.0009(10)
C18 0.0255(10) 0.0275(12) 0.0445(13) 0.0043(10) 0.0044(10) -0.0024(9)
N1 0.0310(10) 0.0495(13) 0.0415(11) 0.0049(10) 0.0141(9) -0.0016(9)
N2 0.0295(10) 0.0375(12) 0.0431(11) 0.0038(9) 0.0154(9) 0.0033(8)
N3 0.0241(9) 0.0294(10) 0.0279(9) 0.0001(7) 0.0070(7) -0.0005(7)
P1 0.0265(3) 0.0257(4) 0.0302(3) -0.0014(2) 0.0088(2) -0.0008(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
C1 N1 1.344(3) . ?
C1 C2 1.379(3) . ?
C1 H1 0.9500 . ?
C2 N3 1.382(3) . ?
C2 C3 1.411(3) . ?
C3 C4 1.358(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.360(3) . ?
C5 H5 0.9500 . ?
C6 N3 1.390(2) . ?
C6 P1 1.834(2) . ?
C7 C12 1.394(3) . ?
C7 C8 1.395(3) . ?
C7 P1 1.828(2) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.372(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.395(3) . ?
C13 C14 1.398(3) . ?
C13 P1 1.830(2) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 N2 1.325(3) . ?
N2 N3 1.353(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
N1 C1 C2 109.88(19) . . ?
N1 C1 H1 125.1 . . ?
C2 C1 H1 125.1 . . ?
C1 C2 N3 102.72(19) . . ?
C1 C2 C3 139.3(2) . . ?
N3 C2 C3 117.94(18) . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 121.89(19) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 N3 115.60(19) . . ?
C5 C6 P1 129.58(16) . . ?
N3 C6 P1 114.64(15) . . ?
C12 C7 C8 118.4(2) . . ?
C12 C7 P1 125.20(17) . . ?
C8 C7 P1 116.22(15) . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 119.8(2) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C18 C13 C14 118.3(2) . . ?
C18 C13 P1 117.27(17) . . ?
C14 C13 P1 124.46(17) . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 121.1(2) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
N2 N1 C1 109.67(18) . . ?
N1 N2 N3 106.28(18) . . ?
N2 N3 C2 111.45(16) . . ?
N2 N3 C6 123.76(18) . . ?
C2 N3 C6 124.78(17) . . ?
C7 P1 C13 104.06(9) . . ?
C7 P1 C6 100.39(9) . . ?
C13 P1 C6 101.48(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
N1 C1 C2 N3 0.3(2) . . . . ?
N1 C1 C2 C3 179.5(3) . . . . ?
C1 C2 C3 C4 -177.7(2) . . . . ?
N3 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 N3 1.0(3) . . . . ?
C4 C5 C6 P1 175.79(16) . . . . ?
C12 C7 C8 C9 -1.5(3) . . . . ?
P1 C7 C8 C9 -176.67(19) . . . . ?
C7 C8 C9 C10 1.8(4) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
P1 C7 C12 C11 174.87(17) . . . . ?
C10 C11 C12 C7 0.9(3) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
P1 C13 C14 C15 179.76(15) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C17 -1.2(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C13 2.5(3) . . . . ?
C14 C13 C18 C17 -2.5(3) . . . . ?
P1 C13 C18 C17 178.37(16) . . . . ?
C2 C1 N1 N2 -0.2(3) . . . . ?
C1 N1 N2 N3 0.0(3) . . . . ?
N1 N2 N3 C2 0.2(2) . . . . ?
N1 N2 N3 C6 -178.48(18) . . . . ?
C1 C2 N3 N2 -0.3(2) . . . . ?
C3 C2 N3 N2 -179.70(18) . . . . ?
C1 C2 N3 C6 178.37(18) . . . . ?
C3 C2 N3 C6 -1.0(3) . . . . ?
C5 C6 N3 N2 178.32(19) . . . . ?
P1 C6 N3 N2 2.8(3) . . . . ?
C5 C6 N3 C2 -0.2(3) . . . . ?
P1 C6 N3 C2 -175.77(16) . . . . ?
C12 C7 P1 C13 4.4(2) . . . . ?
C8 C7 P1 C13 179.12(16) . . . . ?
C12 C7 P1 C6 109.10(18) . . . . ?
C8 C7 P1 C6 -76.14(17) . . . . ?
C18 C13 P1 C7 -75.14(18) . . . . ?
C14 C13 P1 C7 105.81(18) . . . . ?
C18 C13 P1 C6 -179.06(16) . . . . ?
C14 C13 P1 C6 1.89(19) . . . . ?
C5 C6 P1 C7 -2.8(2) . . . . ?
N3 C6 P1 C7 171.98(15) . . . . ?
C5 C6 P1 C13 104.0(2) . . . . ?
N3 C6 P1 C13 -81.21(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.167

# Attachment '- 4c.cif'

data_colo37
_database_code_depnum_ccdc_archive 'CCDC 799868'
#TrackingRef '- 4c.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 N3 P'
_chemical_formula_sum            'C24 H18 N3 P'
_chemical_formula_weight         379.38

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'
P P 0.1023 0.0942 '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 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   6.0164(2)
_cell_length_b                   28.2297(13)
_cell_length_c                   11.5981(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.641(2)
_cell_angle_gamma                90.00
_cell_volume                     1896.89(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    14158
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.159
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11043
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0833
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         27.46
_reflns_number_total             4333
_reflns_number_gt                2730
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_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^)+(0.0875P)^2^+0.8647P] 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         4333
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.2010
_refine_ls_wR_factor_gt          0.1647
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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 0.64321(14) -0.05760(3) 0.69096(8) 0.0313(3) Uani 1 1 d . . .
N1 N 0.5721(4) -0.17367(9) 0.4432(2) 0.0293(6) Uani 1 1 d . . .
N2 N 0.6147(4) -0.13901(9) 0.5239(2) 0.0303(6) Uani 1 1 d . . .
N3 N 0.4129(4) -0.11505(9) 0.5080(2) 0.0257(6) Uani 1 1 d . . .
C1 C 0.3486(5) -0.17256(11) 0.3786(3) 0.0256(7) Uani 1 1 d . . .
C2 C 0.2409(5) -0.13474(11) 0.4174(3) 0.0257(7) Uani 1 1 d . . .
C3 C 0.0203(5) -0.11307(11) 0.3868(3) 0.0296(7) Uani 1 1 d . . .
H3 H -0.1024 -0.1256 0.3246 0.036 Uiso 1 1 calc R . .
C4 C -0.0111(5) -0.07393(12) 0.4489(3) 0.0318(7) Uani 1 1 d . . .
H4 H -0.1568 -0.0585 0.4284 0.038 Uiso 1 1 calc R . .
C5 C 0.1709(5) -0.05562(11) 0.5441(3) 0.0313(7) Uani 1 1 d . . .
H5 H 0.1424 -0.0286 0.5868 0.038 Uiso 1 1 calc R . .
C6 C 0.3841(5) -0.07574(11) 0.5753(3) 0.0281(7) Uani 1 1 d . . .
C7 C 0.2514(5) -0.20873(10) 0.2877(3) 0.0265(7) Uani 1 1 d . . .
C8 C 0.0434(5) -0.23153(12) 0.2864(3) 0.0307(7) Uani 1 1 d . . .
H8 H -0.0407 -0.2222 0.3412 0.037 Uiso 1 1 calc R . .
C9 C -0.0398(5) -0.26773(12) 0.2051(3) 0.0328(7) Uani 1 1 d . . .
H9 H -0.1799 -0.2833 0.2050 0.039 Uiso 1 1 calc R . .
C10 C 0.0808(6) -0.28132(12) 0.1241(3) 0.0344(8) Uani 1 1 d . . .
H10 H 0.0239 -0.3061 0.0686 0.041 Uiso 1 1 calc R . .
C11 C 0.2844(6) -0.25843(12) 0.1247(3) 0.0362(8) Uani 1 1 d . . .
H11 H 0.3662 -0.2675 0.0686 0.043 Uiso 1 1 calc R . .
C12 C 0.3709(5) -0.22252(11) 0.2060(3) 0.0307(7) Uani 1 1 d . . .
H12 H 0.5117 -0.2073 0.2059 0.037 Uiso 1 1 calc R . .
C13 C 0.6642(5) -0.10648(11) 0.7987(3) 0.0308(7) Uani 1 1 d . . .
C14 C 0.4807(6) -0.13529(12) 0.8045(3) 0.0354(8) Uani 1 1 d . . .
H14 H 0.3320 -0.1295 0.7523 0.043 Uiso 1 1 calc R . .
C15 C 0.5116(7) -0.17237(12) 0.8853(3) 0.0414(9) Uani 1 1 d . . .
H15 H 0.3842 -0.1918 0.8882 0.050 Uiso 1 1 calc R . .
C16 C 0.7249(7) -0.18113(14) 0.9613(3) 0.0477(10) Uani 1 1 d . . .
H16 H 0.7459 -0.2068 1.0161 0.057 Uiso 1 1 calc R . .
C17 C 0.9092(7) -0.15262(15) 0.9581(4) 0.0525(11) Uani 1 1 d . . .
H17 H 1.0565 -0.1584 1.0118 0.063 Uiso 1 1 calc R . .
C18 C 0.8805(6) -0.11542(14) 0.8766(3) 0.0411(9) Uani 1 1 d . . .
H18 H 1.0085 -0.0961 0.8742 0.049 Uiso 1 1 calc R . .
C19 C 0.5286(5) -0.00896(11) 0.7624(3) 0.0308(7) Uani 1 1 d . . .
C20 C 0.3595(6) -0.01362(13) 0.8239(3) 0.0413(9) Uani 1 1 d . . .
H20 H 0.2895 -0.0436 0.8270 0.050 Uiso 1 1 calc R . .
C21 C 0.2930(7) 0.02466(14) 0.8801(3) 0.0469(9) Uani 1 1 d . . .
H21 H 0.1754 0.0209 0.9201 0.056 Uiso 1 1 calc R . .
C22 C 0.3946(7) 0.06829(14) 0.8792(3) 0.0469(10) Uani 1 1 d . . .
H22 H 0.3496 0.0943 0.9196 0.056 Uiso 1 1 calc R . .
C23 C 0.5619(7) 0.07396(13) 0.8194(3) 0.0473(10) Uani 1 1 d . . .
H23 H 0.6313 0.1041 0.8175 0.057 Uiso 1 1 calc R . .
C24 C 0.6294(6) 0.03537(12) 0.7616(3) 0.0384(8) Uani 1 1 d . . .
H24 H 0.7458 0.0394 0.7210 0.046 Uiso 1 1 calc R . .

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 0.0311(4) 0.0290(5) 0.0337(5) -0.0037(4) 0.0086(3) -0.0042(4)
N1 0.0284(13) 0.0287(14) 0.0304(14) -0.0018(12) 0.0069(11) -0.0002(11)
N2 0.0259(13) 0.0318(15) 0.0341(15) -0.0031(12) 0.0094(11) 0.0020(12)
N3 0.0265(13) 0.0242(13) 0.0265(14) -0.0014(11) 0.0076(10) 0.0004(11)
C1 0.0258(15) 0.0274(16) 0.0246(16) 0.0039(13) 0.0087(12) 0.0024(13)
C2 0.0265(15) 0.0252(16) 0.0256(15) 0.0012(13) 0.0075(12) -0.0010(13)
C3 0.0273(16) 0.0300(17) 0.0299(17) 0.0014(14) 0.0050(13) -0.0026(14)
C4 0.0286(16) 0.0287(17) 0.0386(19) 0.0036(14) 0.0101(14) 0.0052(14)
C5 0.0330(17) 0.0248(16) 0.0371(19) -0.0015(14) 0.0112(14) 0.0008(14)
C6 0.0357(17) 0.0229(16) 0.0278(17) -0.0018(13) 0.0120(13) -0.0024(14)
C7 0.0276(16) 0.0241(16) 0.0264(16) 0.0025(12) 0.0051(12) 0.0045(13)
C8 0.0282(16) 0.0337(18) 0.0294(17) 0.0010(14) 0.0066(13) 0.0026(14)
C9 0.0268(16) 0.0346(18) 0.0335(18) -0.0020(15) 0.0022(13) -0.0006(14)
C10 0.0354(18) 0.0340(19) 0.0273(18) -0.0053(14) -0.0029(13) 0.0033(15)
C11 0.0385(19) 0.040(2) 0.0302(18) -0.0054(15) 0.0098(14) 0.0077(16)
C12 0.0278(16) 0.0325(18) 0.0311(18) -0.0004(14) 0.0065(13) 0.0030(14)
C13 0.0326(17) 0.0281(17) 0.0308(18) -0.0051(14) 0.0068(13) -0.0002(14)
C14 0.0366(18) 0.0340(19) 0.0331(19) -0.0027(15) 0.0048(14) -0.0023(15)
C15 0.058(2) 0.0296(19) 0.037(2) -0.0025(15) 0.0125(17) -0.0036(17)
C16 0.070(3) 0.038(2) 0.036(2) 0.0056(16) 0.0155(19) 0.016(2)
C17 0.047(2) 0.062(3) 0.045(2) 0.004(2) 0.0056(17) 0.022(2)
C18 0.0318(18) 0.048(2) 0.042(2) -0.0012(17) 0.0073(15) 0.0025(17)
C19 0.0331(17) 0.0283(17) 0.0298(17) -0.0013(14) 0.0066(13) -0.0006(14)
C20 0.044(2) 0.0350(19) 0.048(2) -0.0083(17) 0.0185(17) -0.0066(17)
C21 0.049(2) 0.051(2) 0.042(2) -0.0058(18) 0.0144(17) 0.0053(19)
C22 0.063(2) 0.037(2) 0.036(2) -0.0066(16) 0.0041(18) 0.0104(19)
C23 0.065(3) 0.0285(19) 0.046(2) -0.0027(17) 0.0094(19) -0.0033(18)
C24 0.046(2) 0.0298(19) 0.039(2) -0.0003(15) 0.0096(16) -0.0066(16)

_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 C19 1.832(3) . ?
P1 C6 1.834(3) . ?
P1 C13 1.843(3) . ?
N1 N2 1.330(4) . ?
N1 C1 1.352(4) . ?
N2 N3 1.358(3) . ?
N3 C2 1.378(4) . ?
N3 C6 1.394(4) . ?
C1 C2 1.385(4) . ?
C1 C7 1.471(4) . ?
C2 C3 1.417(4) . ?
C3 C4 1.359(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.426(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.360(4) . ?
C5 H5 0.9500 . ?
C7 C12 1.391(4) . ?
C7 C8 1.404(4) . ?
C8 C9 1.389(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.387(5) . ?
C13 C18 1.393(5) . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.392(4) . ?
C19 C20 1.398(5) . ?
C20 C21 1.376(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.377(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 P1 C6 101.00(14) . . ?
C19 P1 C13 102.68(15) . . ?
C6 P1 C13 100.13(14) . . ?
N2 N1 C1 110.3(2) . . ?
N1 N2 N3 106.0(2) . . ?
N2 N3 C2 111.3(2) . . ?
N2 N3 C6 124.2(2) . . ?
C2 N3 C6 124.6(3) . . ?
N1 C1 C2 108.7(3) . . ?
N1 C1 C7 121.7(3) . . ?
C2 C1 C7 129.5(3) . . ?
N3 C2 C1 103.7(2) . . ?
N3 C2 C3 118.5(3) . . ?
C1 C2 C3 137.8(3) . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.8(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 N3 115.7(3) . . ?
C5 C6 P1 129.3(2) . . ?
N3 C6 P1 115.0(2) . . ?
C12 C7 C8 119.2(3) . . ?
C12 C7 C1 120.3(3) . . ?
C8 C7 C1 120.5(3) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C14 C13 C18 118.6(3) . . ?
C14 C13 P1 124.2(2) . . ?
C18 C13 P1 117.2(3) . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.9(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C24 C19 C20 117.8(3) . . ?
C24 C19 P1 116.9(3) . . ?
C20 C19 P1 125.1(3) . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 120.8(4) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 119.7(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C23 121.0(3) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?

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
C1 N1 N2 N3 -1.0(3) . . . . ?
N1 N2 N3 C2 0.4(3) . . . . ?
N1 N2 N3 C6 -179.9(3) . . . . ?
N2 N1 C1 C2 1.2(3) . . . . ?
N2 N1 C1 C7 -176.4(3) . . . . ?
N2 N3 C2 C1 0.3(3) . . . . ?
C6 N3 C2 C1 -179.4(3) . . . . ?
N2 N3 C2 C3 -178.2(3) . . . . ?
C6 N3 C2 C3 2.1(4) . . . . ?
N1 C1 C2 N3 -0.9(3) . . . . ?
C7 C1 C2 N3 176.4(3) . . . . ?
N1 C1 C2 C3 177.1(4) . . . . ?
C7 C1 C2 C3 -5.5(6) . . . . ?
N3 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C4 -178.1(3) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C4 C5 C6 N3 0.4(5) . . . . ?
C4 C5 C6 P1 178.4(2) . . . . ?
N2 N3 C6 C5 178.2(3) . . . . ?
C2 N3 C6 C5 -2.1(4) . . . . ?
N2 N3 C6 P1 -0.1(4) . . . . ?
C2 N3 C6 P1 179.6(2) . . . . ?
C19 P1 C6 C5 5.5(3) . . . . ?
C13 P1 C6 C5 110.7(3) . . . . ?
C19 P1 C6 N3 -176.5(2) . . . . ?
C13 P1 C6 N3 -71.3(2) . . . . ?
N1 C1 C7 C12 -45.7(4) . . . . ?
C2 C1 C7 C12 137.2(3) . . . . ?
N1 C1 C7 C8 130.9(3) . . . . ?
C2 C1 C7 C8 -46.2(5) . . . . ?
C12 C7 C8 C9 0.7(5) . . . . ?
C1 C7 C8 C9 -175.9(3) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C10 C11 C12 C7 -0.6(5) . . . . ?
C8 C7 C12 C11 -0.1(5) . . . . ?
C1 C7 C12 C11 176.5(3) . . . . ?
C19 P1 C13 C14 82.4(3) . . . . ?
C6 P1 C13 C14 -21.4(3) . . . . ?
C19 P1 C13 C18 -99.4(3) . . . . ?
C6 P1 C13 C18 156.8(3) . . . . ?
C18 C13 C14 C15 -0.4(5) . . . . ?
P1 C13 C14 C15 177.8(3) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 C17 0.7(6) . . . . ?
C15 C16 C17 C18 -1.1(6) . . . . ?
C16 C17 C18 C13 0.8(6) . . . . ?
C14 C13 C18 C17 0.0(5) . . . . ?
P1 C13 C18 C17 -178.4(3) . . . . ?
C6 P1 C19 C24 -120.6(3) . . . . ?
C13 P1 C19 C24 136.3(3) . . . . ?
C6 P1 C19 C20 63.7(3) . . . . ?
C13 P1 C19 C20 -39.4(3) . . . . ?
C24 C19 C20 C21 0.9(5) . . . . ?
P1 C19 C20 C21 176.6(3) . . . . ?
C19 C20 C21 C22 -1.3(6) . . . . ?
C20 C21 C22 C23 1.2(6) . . . . ?
C21 C22 C23 C24 -0.8(6) . . . . ?
C20 C19 C24 C23 -0.6(5) . . . . ?
P1 C19 C24 C23 -176.6(3) . . . . ?
C22 C23 C24 C19 0.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.103

# Attachment '- 5a.cif'

data_colo38
_database_code_depnum_ccdc_archive 'CCDC 799869'
#TrackingRef '- 5a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H28 N3 P'
_chemical_formula_sum            'C19 H28 N3 P'
_chemical_formula_weight         329.41

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'
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                   11.1873(7)
_cell_length_b                   11.4055(7)
_cell_length_c                   16.9232(8)
_cell_angle_alpha                100.619(3)
_cell_angle_beta                 90.506(3)
_cell_angle_gamma                119.238(2)
_cell_volume                     1839.63(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    16205
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.153
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19790
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_sigmaI/netI    0.1199
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         27.43
_reflns_number_total             8370
_reflns_number_gt                4333
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_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^)+(0.1076P)^2^+0.0000P] 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         8370
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.2208
_refine_ls_wR_factor_gt          0.1652
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5325(3) 0.2621(3) 0.19165(18) 0.0353(8) Uani 1 1 d . . .
C2 C 0.6244(3) 0.2740(3) 0.13523(19) 0.0355(8) Uani 1 1 d . . .
C3 C 0.6516(4) 0.1852(4) 0.0795(2) 0.0519(10) Uani 1 1 d . . .
H3 H 0.6026 0.0889 0.0770 0.062 Uiso 1 1 calc R . .
C4 C 0.7485(4) 0.2383(4) 0.0297(3) 0.0666(12) Uani 1 1 d . . .
H4 H 0.7664 0.1796 -0.0097 0.080 Uiso 1 1 calc R . .
C5 C 0.8240(4) 0.3843(4) 0.0368(2) 0.0578(11) Uani 1 1 d . . .
H5 H 0.8920 0.4198 0.0013 0.069 Uiso 1 1 calc R . .
C6 C 0.8045(3) 0.4746(3) 0.0910(2) 0.0408(8) Uani 1 1 d . . .
C7 C 0.4229(4) 0.1332(3) 0.2129(2) 0.0480(9) Uani 1 1 d . . .
H7A H 0.3687 0.1559 0.2516 0.072 Uiso 1 1 calc R . .
H7B H 0.4658 0.0891 0.2371 0.072 Uiso 1 1 calc R . .
H7C H 0.3622 0.0703 0.1638 0.072 Uiso 1 1 calc R . .
C8 C 0.8036(3) 0.7298(3) 0.09065(18) 0.0375(8) Uani 1 1 d . . .
H8 H 0.7499 0.7239 0.1381 0.045 Uiso 1 1 calc R . .
C9 C 0.7045(4) 0.6470(3) 0.0132(2) 0.0520(10) Uani 1 1 d . . .
H9A H 0.7584 0.6416 -0.0320 0.062 Uiso 1 1 calc R . .
H9B H 0.6423 0.5521 0.0199 0.062 Uiso 1 1 calc R . .
C10 C 0.6185(4) 0.7079(4) -0.0085(2) 0.0600(11) Uani 1 1 d . . .
H10A H 0.5534 0.6994 0.0322 0.072 Uiso 1 1 calc R . .
H10B H 0.5637 0.6549 -0.0617 0.072 Uiso 1 1 calc R . .
C11 C 0.7061(4) 0.8584(3) -0.0123(2) 0.0479(9) Uani 1 1 d . . .
H11A H 0.7620 0.8663 -0.0582 0.057 Uiso 1 1 calc R . .
H11B H 0.6454 0.8961 -0.0216 0.057 Uiso 1 1 calc R . .
C12 C 0.8005(4) 0.9407(3) 0.0656(2) 0.0559(11) Uani 1 1 d . . .
H12A H 0.7446 0.9401 0.1107 0.067 Uiso 1 1 calc R . .
H12B H 0.8600 1.0373 0.0610 0.067 Uiso 1 1 calc R . .
C13 C 0.8896(4) 0.8808(4) 0.0836(2) 0.0583(11) Uani 1 1 d . . .
H13A H 0.9500 0.9360 0.1349 0.070 Uiso 1 1 calc R . .
H13B H 0.9494 0.8869 0.0399 0.070 Uiso 1 1 calc R . .
C14 C 0.9780(3) 0.7107(3) 0.2150(2) 0.0422(9) Uani 1 1 d . . .
H14 H 0.8949 0.6710 0.2446 0.051 Uiso 1 1 calc R . .
C15 C 1.0667(6) 0.6483(5) 0.2302(3) 0.0936(18) Uani 1 1 d . . .
H15A H 1.1406 0.6757 0.1942 0.112 Uiso 1 1 calc R . .
H15B H 1.0091 0.5468 0.2158 0.112 Uiso 1 1 calc R . .
C16 C 1.1323(6) 0.6917(4) 0.3174(3) 0.0915(18) Uani 1 1 d . . .
H16A H 1.0591 0.6532 0.3529 0.110 Uiso 1 1 calc R . .
H16B H 1.1940 0.6533 0.3219 0.110 Uiso 1 1 calc R . .
C17 C 1.2137(4) 0.8455(4) 0.3454(2) 0.0539(10) Uani 1 1 d . . .
H17A H 1.2488 0.8698 0.4034 0.065 Uiso 1 1 calc R . .
H17B H 1.2938 0.8835 0.3143 0.065 Uiso 1 1 calc R . .
C18 C 1.1249(4) 0.9068(4) 0.3337(2) 0.0588(11) Uani 1 1 d . . .
H18A H 1.1817 1.0084 0.3491 0.071 Uiso 1 1 calc R . .
H18B H 1.0516 0.8772 0.3701 0.071 Uiso 1 1 calc R . .
C19 C 1.0585(4) 0.8647(4) 0.2465(2) 0.0593(11) Uani 1 1 d . . .
H19A H 0.9959 0.9023 0.2432 0.071 Uiso 1 1 calc R . .
H19B H 1.1316 0.9060 0.2113 0.071 Uiso 1 1 calc R . .
C20 C 0.5176(4) -0.2354(3) 0.2335(2) 0.0471(9) Uani 1 1 d . . .
C21 C 0.6151(3) -0.2013(3) 0.2971(2) 0.0415(8) Uani 1 1 d . . .
C22 C 0.6613(4) -0.2707(4) 0.3385(2) 0.0498(10) Uani 1 1 d . . .
H22 H 0.6215 -0.3678 0.3233 0.060 Uiso 1 1 calc R . .
C23 C 0.7632(4) -0.1966(4) 0.4001(2) 0.0522(10) Uani 1 1 d . . .
H23 H 0.7974 -0.2415 0.4276 0.063 Uiso 1 1 calc R . .
C24 C 0.8197(4) -0.0526(4) 0.4243(2) 0.0451(9) Uani 1 1 d . . .
H24 H 0.8886 -0.0041 0.4695 0.054 Uiso 1 1 calc R . .
C25 C 0.7799(3) 0.0204(3) 0.38573(19) 0.0381(8) Uani 1 1 d . . .
C26 C 0.4180(4) -0.3744(4) 0.1832(2) 0.0614(11) Uani 1 1 d . . .
H26A H 0.3447 -0.4252 0.2152 0.092 Uiso 1 1 calc R . .
H26B H 0.4665 -0.4251 0.1663 0.092 Uiso 1 1 calc R . .
H26C H 0.3776 -0.3638 0.1353 0.092 Uiso 1 1 calc R . .
C27 C 0.7250(3) 0.2497(3) 0.40928(19) 0.0370(8) Uani 1 1 d . . .
H27 H 0.6939 0.2272 0.3501 0.044 Uiso 1 1 calc R . .
C28 C 0.6028(3) 0.1649(3) 0.4533(2) 0.0434(9) Uani 1 1 d . . .
H28A H 0.5619 0.0662 0.4274 0.052 Uiso 1 1 calc R . .
H28B H 0.6368 0.1774 0.5102 0.052 Uiso 1 1 calc R . .
C29 C 0.4914(4) 0.2049(4) 0.4524(2) 0.0493(9) Uani 1 1 d . . .
H29A H 0.4487 0.1811 0.3961 0.059 Uiso 1 1 calc R . .
H29B H 0.4187 0.1515 0.4848 0.059 Uiso 1 1 calc R . .
C30 C 0.5493(4) 0.3578(4) 0.4866(2) 0.0568(10) Uani 1 1 d . . .
H30A H 0.4758 0.3813 0.4813 0.068 Uiso 1 1 calc R . .
H30B H 0.5821 0.3800 0.5448 0.068 Uiso 1 1 calc R . .
C31 C 0.6677(4) 0.4419(4) 0.4416(2) 0.0539(10) Uani 1 1 d . . .
H31A H 0.7072 0.5408 0.4664 0.065 Uiso 1 1 calc R . .
H31B H 0.6323 0.4266 0.3847 0.065 Uiso 1 1 calc R . .
C32 C 0.7814(4) 0.4041(3) 0.4435(2) 0.0459(9) Uani 1 1 d . . .
H32A H 0.8236 0.4286 0.5000 0.055 Uiso 1 1 calc R . .
H32B H 0.8541 0.4581 0.4113 0.055 Uiso 1 1 calc R . .
C33 C 0.9860(3) 0.2775(3) 0.35008(19) 0.0395(8) Uani 1 1 d . . .
H33 H 1.0233 0.3792 0.3631 0.047 Uiso 1 1 calc R . .
C34 C 1.1082(4) 0.2563(4) 0.3662(2) 0.0543(10) Uani 1 1 d . . .
H34A H 1.1453 0.2949 0.4240 0.065 Uiso 1 1 calc R . .
H34B H 1.0754 0.1564 0.3553 0.065 Uiso 1 1 calc R . .
C35 C 1.2233(4) 0.3239(4) 0.3145(2) 0.0578(10) Uani 1 1 d . . .
H35A H 1.2629 0.4249 0.3290 0.069 Uiso 1 1 calc R . .
H35B H 1.2975 0.3034 0.3254 0.069 Uiso 1 1 calc R . .
C36 C 1.1694(4) 0.2718(4) 0.2253(2) 0.0511(10) Uani 1 1 d . . .
H36A H 1.1377 0.1722 0.2095 0.061 Uiso 1 1 calc R . .
H36B H 1.2445 0.3203 0.1928 0.061 Uiso 1 1 calc R . .
C37 C 1.0508(4) 0.2959(4) 0.2081(2) 0.0530(10) Uani 1 1 d . . .
H37A H 1.0145 0.2581 0.1501 0.064 Uiso 1 1 calc R . .
H37B H 1.0850 0.3962 0.2193 0.064 Uiso 1 1 calc R . .
C38 C 0.9342(3) 0.2283(4) 0.25961(19) 0.0465(9) Uani 1 1 d . . .
H38A H 0.8933 0.1271 0.2442 0.056 Uiso 1 1 calc R . .
H38B H 0.8612 0.2504 0.2487 0.056 Uiso 1 1 calc R . .
N1 N 0.5533(3) 0.3883(3) 0.22524(15) 0.0392(7) Uani 1 1 d . . .
N2 N 0.6560(3) 0.4832(3) 0.19351(15) 0.0361(6) Uani 1 1 d . . .
N3 N 0.7000(3) 0.4150(2) 0.13905(15) 0.0330(6) Uani 1 1 d . . .
N4 N 0.5244(3) -0.1185(3) 0.22048(17) 0.0489(8) Uani 1 1 d . . .
N5 N 0.6203(3) -0.0100(3) 0.27317(17) 0.0447(7) Uani 1 1 d . . .
N6 N 0.6763(3) -0.0591(2) 0.32034(16) 0.0368(7) Uani 1 1 d . . .
P1 P 0.92062(9) 0.66163(9) 0.10451(5) 0.0399(3) Uani 1 1 d . . .
P2 P 0.86205(9) 0.20712(9) 0.42435(5) 0.0389(3) 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
C1 0.0360(19) 0.0323(18) 0.0372(18) 0.0059(14) -0.0013(14) 0.0174(15)
C2 0.0351(18) 0.0242(16) 0.0432(18) 0.0034(14) -0.0008(15) 0.0132(14)
C3 0.046(2) 0.0279(18) 0.076(3) 0.0015(18) 0.0106(19) 0.0168(17)
C4 0.064(3) 0.037(2) 0.086(3) -0.009(2) 0.025(2) 0.023(2)
C5 0.046(2) 0.038(2) 0.074(3) -0.0019(19) 0.0233(19) 0.0131(18)
C6 0.0362(19) 0.0321(18) 0.047(2) 0.0016(15) 0.0098(15) 0.0140(15)
C7 0.047(2) 0.040(2) 0.056(2) 0.0232(17) 0.0070(17) 0.0174(17)
C8 0.0386(19) 0.0320(17) 0.0347(17) 0.0070(14) 0.0044(14) 0.0122(15)
C9 0.054(2) 0.0261(18) 0.054(2) 0.0019(16) -0.0141(18) 0.0060(17)
C10 0.056(2) 0.041(2) 0.067(3) 0.0104(19) -0.0176(19) 0.0125(19)
C11 0.058(2) 0.0352(19) 0.044(2) 0.0062(16) -0.0051(17) 0.0199(18)
C12 0.072(3) 0.0323(19) 0.052(2) -0.0015(17) -0.0142(19) 0.0216(19)
C13 0.060(3) 0.034(2) 0.067(3) -0.0007(18) -0.017(2) 0.0180(19)
C14 0.0358(19) 0.0270(17) 0.054(2) 0.0064(15) -0.0005(15) 0.0091(15)
C15 0.138(5) 0.062(3) 0.092(3) -0.015(3) -0.041(3) 0.070(3)
C16 0.134(4) 0.054(3) 0.090(3) 0.004(2) -0.042(3) 0.054(3)
C17 0.049(2) 0.056(2) 0.054(2) 0.0099(19) -0.0079(17) 0.0256(19)
C18 0.064(3) 0.041(2) 0.066(3) -0.0056(18) -0.019(2) 0.029(2)
C19 0.068(3) 0.036(2) 0.064(2) 0.0001(18) -0.023(2) 0.0219(19)
C20 0.041(2) 0.0295(18) 0.061(2) -0.0011(16) 0.0150(18) 0.0135(16)
C21 0.043(2) 0.0243(17) 0.055(2) 0.0050(15) 0.0179(17) 0.0162(15)
C22 0.066(3) 0.0311(19) 0.062(2) 0.0186(18) 0.032(2) 0.0275(19)
C23 0.071(3) 0.046(2) 0.060(2) 0.0240(19) 0.022(2) 0.040(2)
C24 0.051(2) 0.045(2) 0.049(2) 0.0141(17) 0.0106(16) 0.0295(18)
C25 0.041(2) 0.0328(18) 0.0453(19) 0.0105(15) 0.0081(15) 0.0216(16)
C26 0.055(2) 0.032(2) 0.074(3) -0.0057(18) 0.007(2) 0.0102(18)
C27 0.047(2) 0.0247(16) 0.0387(18) 0.0039(14) 0.0013(15) 0.0184(15)
C28 0.048(2) 0.0328(18) 0.050(2) 0.0095(16) 0.0084(16) 0.0205(16)
C29 0.051(2) 0.045(2) 0.057(2) 0.0066(18) 0.0080(17) 0.0297(18)
C30 0.066(3) 0.049(2) 0.065(2) 0.0045(19) 0.010(2) 0.039(2)
C31 0.074(3) 0.0328(19) 0.060(2) 0.0043(17) -0.001(2) 0.0331(19)
C32 0.056(2) 0.0267(17) 0.048(2) 0.0038(15) 0.0042(17) 0.0173(17)
C33 0.043(2) 0.0273(17) 0.0452(19) 0.0029(14) 0.0026(15) 0.0166(15)
C34 0.046(2) 0.064(3) 0.054(2) 0.0100(19) -0.0004(17) 0.029(2)
C35 0.041(2) 0.059(3) 0.067(3) 0.006(2) 0.0051(18) 0.023(2)
C36 0.050(2) 0.034(2) 0.060(2) 0.0041(17) 0.0138(18) 0.0157(17)
C37 0.059(2) 0.040(2) 0.048(2) 0.0107(17) 0.0069(18) 0.0145(18)
C38 0.042(2) 0.045(2) 0.048(2) 0.0103(17) 0.0014(16) 0.0187(17)
N1 0.0394(16) 0.0344(15) 0.0422(15) 0.0080(13) 0.0068(12) 0.0173(13)
N2 0.0377(16) 0.0320(15) 0.0372(15) 0.0018(12) 0.0071(12) 0.0181(13)
N3 0.0328(15) 0.0256(13) 0.0379(14) 0.0015(11) 0.0018(11) 0.0142(12)
N4 0.0418(18) 0.0345(16) 0.0601(19) -0.0060(14) -0.0038(14) 0.0167(14)
N5 0.0438(17) 0.0320(15) 0.0536(17) -0.0002(13) -0.0036(14) 0.0188(14)
N6 0.0386(16) 0.0244(14) 0.0482(16) 0.0073(12) 0.0059(13) 0.0167(12)
P1 0.0356(5) 0.0286(5) 0.0453(5) 0.0020(4) 0.0070(4) 0.0102(4)
P2 0.0421(5) 0.0303(5) 0.0424(5) 0.0038(4) 0.0014(4) 0.0180(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.348(4) . ?
C1 C2 1.384(4) . ?
C1 C7 1.495(4) . ?
C2 N3 1.392(4) . ?
C2 C3 1.401(5) . ?
C3 C4 1.347(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.432(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.351(5) . ?
C5 H5 0.9500 . ?
C6 N3 1.391(4) . ?
C6 P1 1.843(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.527(4) . ?
C8 C13 1.538(4) . ?
C8 P1 1.852(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.512(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.520(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.511(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.514(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.510(4) . ?
C14 C15 1.520(6) . ?
C14 P1 1.861(3) . ?
C14 H14 1.0000 . ?
C15 C16 1.522(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.502(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.497(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.527(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 N4 1.357(4) . ?
C20 C21 1.383(5) . ?
C20 C26 1.496(5) . ?
C21 N6 1.388(4) . ?
C21 C22 1.408(5) . ?
C22 C23 1.346(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.414(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.368(4) . ?
C24 H24 0.9500 . ?
C25 N6 1.404(4) . ?
C25 P2 1.837(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.534(4) . ?
C27 C32 1.539(4) . ?
C27 P2 1.849(3) . ?
C27 H27 1.0000 . ?
C28 C29 1.523(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.521(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.516(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.531(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.530(5) . ?
C33 C38 1.531(4) . ?
C33 P2 1.861(3) . ?
C33 H33 1.0000 . ?
C34 C35 1.523(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.516(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.517(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.530(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
N1 N2 1.338(3) . ?
N2 N3 1.347(4) . ?
N4 N5 1.325(4) . ?
N5 N6 1.357(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
N1 C1 C2 109.1(3) . . ?
N1 C1 C7 123.2(3) . . ?
C2 C1 C7 127.7(3) . . ?
C1 C2 N3 103.6(3) . . ?
C1 C2 C3 137.1(3) . . ?
N3 C2 C3 119.3(3) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 124.1(3) . . ?
C6 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C5 C6 N3 114.8(3) . . ?
C5 C6 P1 121.0(3) . . ?
N3 C6 P1 123.9(2) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 108.7(3) . . ?
C9 C8 P1 110.1(2) . . ?
C13 C8 P1 109.2(2) . . ?
C9 C8 H8 109.6 . . ?
C13 C8 H8 109.6 . . ?
P1 C8 H8 109.6 . . ?
C10 C9 C8 113.3(3) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 112.4(3) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 110.6(3) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 110.7(3) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C8 112.3(3) . . ?
C12 C13 H13A 109.1 . . ?
C8 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C8 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C19 C14 C15 109.8(3) . . ?
C19 C14 P1 112.7(2) . . ?
C15 C14 P1 108.0(3) . . ?
C19 C14 H14 108.8 . . ?
C15 C14 H14 108.8 . . ?
P1 C14 H14 108.8 . . ?
C14 C15 C16 113.6(4) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 111.9(3) . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 110.2(3) . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 112.4(3) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C14 C19 C18 113.3(3) . . ?
C14 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C14 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
N4 C20 C21 108.9(3) . . ?
N4 C20 C26 122.3(3) . . ?
C21 C20 C26 128.9(3) . . ?
C20 C21 N6 103.5(3) . . ?
C20 C21 C22 137.2(3) . . ?
N6 C21 C22 119.3(3) . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 123.2(3) . . ?
C25 C24 H24 118.4 . . ?
C23 C24 H24 118.4 . . ?
C24 C25 N6 114.8(3) . . ?
C24 C25 P2 118.3(3) . . ?
N6 C25 P2 126.9(2) . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C32 109.7(3) . . ?
C28 C27 P2 109.2(2) . . ?
C32 C27 P2 109.5(2) . . ?
C28 C27 H27 109.5 . . ?
C32 C27 H27 109.5 . . ?
P2 C27 H27 109.5 . . ?
C29 C28 C27 112.9(3) . . ?
C29 C28 H28A 109.0 . . ?
C27 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C27 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C30 C29 C28 111.8(3) . . ?
C30 C29 H29A 109.3 . . ?
C28 C29 H29A 109.3 . . ?
C30 C29 H29B 109.3 . . ?
C28 C29 H29B 109.3 . . ?
H29A C29 H29B 107.9 . . ?
C31 C30 C29 110.3(3) . . ?
C31 C30 H30A 109.6 . . ?
C29 C30 H30A 109.6 . . ?
C31 C30 H30B 109.6 . . ?
C29 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
C30 C31 C32 112.1(3) . . ?
C30 C31 H31A 109.2 . . ?
C32 C31 H31A 109.2 . . ?
C30 C31 H31B 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C31 C32 C27 111.7(3) . . ?
C31 C32 H32A 109.3 . . ?
C27 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C27 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C34 C33 C38 109.7(3) . . ?
C34 C33 P2 108.5(2) . . ?
C38 C33 P2 119.1(2) . . ?
C34 C33 H33 106.3 . . ?
C38 C33 H33 106.3 . . ?
P2 C33 H33 106.3 . . ?
C35 C34 C33 112.8(3) . . ?
C35 C34 H34A 109.0 . . ?
C33 C34 H34A 109.0 . . ?
C35 C34 H34B 109.0 . . ?
C33 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
C36 C35 C34 110.8(3) . . ?
C36 C35 H35A 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C35 C36 C37 110.3(3) . . ?
C35 C36 H36A 109.6 . . ?
C37 C36 H36A 109.6 . . ?
C35 C36 H36B 109.6 . . ?
C37 C36 H36B 109.6 . . ?
H36A C36 H36B 108.1 . . ?
C36 C37 C38 111.8(3) . . ?
C36 C37 H37A 109.3 . . ?
C38 C37 H37A 109.3 . . ?
C36 C37 H37B 109.3 . . ?
C38 C37 H37B 109.3 . . ?
H37A C37 H37B 107.9 . . ?
C37 C38 C33 111.6(3) . . ?
C37 C38 H38A 109.3 . . ?
C33 C38 H38A 109.3 . . ?
C37 C38 H38B 109.3 . . ?
C33 C38 H38B 109.3 . . ?
H38A C38 H38B 108.0 . . ?
N2 N1 C1 109.9(3) . . ?
N1 N2 N3 106.6(2) . . ?
N2 N3 C6 125.6(3) . . ?
N2 N3 C2 110.9(2) . . ?
C6 N3 C2 123.5(3) . . ?
N5 N4 C20 110.3(3) . . ?
N4 N5 N6 106.3(3) . . ?
N5 N6 C21 111.1(3) . . ?
N5 N6 C25 125.6(3) . . ?
C21 N6 C25 123.3(3) . . ?
C6 P1 C8 104.22(15) . . ?
C6 P1 C14 100.94(14) . . ?
C8 P1 C14 106.00(16) . . ?
C25 P2 C27 105.17(14) . . ?
C25 P2 C33 102.82(15) . . ?
C27 P2 C33 107.04(14) . . ?

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
N1 C1 C2 N3 0.5(3) . . . . ?
C7 C1 C2 N3 178.7(3) . . . . ?
N1 C1 C2 C3 -177.0(4) . . . . ?
C7 C1 C2 C3 1.2(6) . . . . ?
C1 C2 C3 C4 175.7(4) . . . . ?
N3 C2 C3 C4 -1.5(5) . . . . ?
C2 C3 C4 C5 2.1(6) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C4 C5 C6 N3 -2.1(6) . . . . ?
C4 C5 C6 P1 172.3(3) . . . . ?
C13 C8 C9 C10 -52.6(4) . . . . ?
P1 C8 C9 C10 -172.2(2) . . . . ?
C8 C9 C10 C11 53.3(4) . . . . ?
C9 C10 C11 C12 -54.0(5) . . . . ?
C10 C11 C12 C13 56.3(4) . . . . ?
C11 C12 C13 C8 -58.6(4) . . . . ?
C9 C8 C13 C12 55.4(4) . . . . ?
P1 C8 C13 C12 175.5(3) . . . . ?
C19 C14 C15 C16 51.3(5) . . . . ?
P1 C14 C15 C16 174.5(4) . . . . ?
C14 C15 C16 C17 -54.6(6) . . . . ?
C15 C16 C17 C18 55.0(6) . . . . ?
C16 C17 C18 C19 -55.1(5) . . . . ?
C15 C14 C19 C18 -50.9(5) . . . . ?
P1 C14 C19 C18 -171.2(3) . . . . ?
C17 C18 C19 C14 54.5(5) . . . . ?
N4 C20 C21 N6 0.8(4) . . . . ?
C26 C20 C21 N6 -179.8(3) . . . . ?
N4 C20 C21 C22 -178.7(4) . . . . ?
C26 C20 C21 C22 0.7(7) . . . . ?
C20 C21 C22 C23 -180.0(4) . . . . ?
N6 C21 C22 C23 0.6(5) . . . . ?
C21 C22 C23 C24 1.9(5) . . . . ?
C22 C23 C24 C25 -2.7(6) . . . . ?
C23 C24 C25 N6 0.9(5) . . . . ?
C23 C24 C25 P2 179.7(3) . . . . ?
C32 C27 C28 C29 53.4(4) . . . . ?
P2 C27 C28 C29 173.4(2) . . . . ?
C27 C28 C29 C30 -55.1(4) . . . . ?
C28 C29 C30 C31 55.0(4) . . . . ?
C29 C30 C31 C32 -56.0(4) . . . . ?
C30 C31 C32 C27 56.2(4) . . . . ?
C28 C27 C32 C31 -53.5(4) . . . . ?
P2 C27 C32 C31 -173.3(2) . . . . ?
C38 C33 C34 C35 54.5(4) . . . . ?
P2 C33 C34 C35 -173.9(3) . . . . ?
C33 C34 C35 C36 -56.5(4) . . . . ?
C34 C35 C36 C37 56.4(4) . . . . ?
C35 C36 C37 C38 -56.8(4) . . . . ?
C36 C37 C38 C33 56.0(4) . . . . ?
C34 C33 C38 C37 -53.6(4) . . . . ?
P2 C33 C38 C37 -179.3(3) . . . . ?
C2 C1 N1 N2 -0.4(3) . . . . ?
C7 C1 N1 N2 -178.7(3) . . . . ?
C1 N1 N2 N3 0.1(3) . . . . ?
N1 N2 N3 C6 178.8(3) . . . . ?
N1 N2 N3 C2 0.2(3) . . . . ?
C5 C6 N3 N2 -175.6(3) . . . . ?
P1 C6 N3 N2 10.1(4) . . . . ?
C5 C6 N3 C2 2.8(5) . . . . ?
P1 C6 N3 C2 -171.6(2) . . . . ?
C1 C2 N3 N2 -0.5(3) . . . . ?
C3 C2 N3 N2 177.6(3) . . . . ?
C1 C2 N3 C6 -179.1(3) . . . . ?
C3 C2 N3 C6 -1.0(5) . . . . ?
C21 C20 N4 N5 -0.8(4) . . . . ?
C26 C20 N4 N5 179.7(3) . . . . ?
C20 N4 N5 N6 0.4(4) . . . . ?
N4 N5 N6 C21 0.1(4) . . . . ?
N4 N5 N6 C25 -178.3(3) . . . . ?
C20 C21 N6 N5 -0.5(4) . . . . ?
C22 C21 N6 N5 179.1(3) . . . . ?
C20 C21 N6 C25 177.9(3) . . . . ?
C22 C21 N6 C25 -2.5(5) . . . . ?
C24 C25 N6 N5 179.9(3) . . . . ?
P2 C25 N6 N5 1.2(5) . . . . ?
C24 C25 N6 C21 1.7(4) . . . . ?
P2 C25 N6 C21 -177.0(2) . . . . ?
C5 C6 P1 C8 126.0(3) . . . . ?
N3 C6 P1 C8 -60.1(3) . . . . ?
C5 C6 P1 C14 -124.2(3) . . . . ?
N3 C6 P1 C14 49.7(3) . . . . ?
C9 C8 P1 C6 -49.5(2) . . . . ?
C13 C8 P1 C6 -168.8(2) . . . . ?
C9 C8 P1 C14 -155.5(2) . . . . ?
C13 C8 P1 C14 85.2(3) . . . . ?
C19 C14 P1 C6 -170.9(3) . . . . ?
C15 C14 P1 C6 67.7(3) . . . . ?
C19 C14 P1 C8 -62.5(3) . . . . ?
C15 C14 P1 C8 176.2(3) . . . . ?
C24 C25 P2 C27 -144.7(3) . . . . ?
N6 C25 P2 C27 34.0(3) . . . . ?
C24 C25 P2 C33 103.4(3) . . . . ?
N6 C25 P2 C33 -77.9(3) . . . . ?
C28 C27 P2 C25 57.3(2) . . . . ?
C32 C27 P2 C25 177.4(2) . . . . ?
C28 C27 P2 C33 166.1(2) . . . . ?
C32 C27 P2 C33 -73.7(2) . . . . ?
C34 C33 P2 C25 -74.8(2) . . . . ?
C38 C33 P2 C25 51.5(3) . . . . ?
C34 C33 P2 C27 174.7(2) . . . . ?
C38 C33 P2 C27 -59.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.122

# Attachment '- 5b.cif'

data_colo33
_database_code_depnum_ccdc_archive 'CCDC 799870'
#TrackingRef '- 5b.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H26 N3 P'
_chemical_formula_sum            'C18 H26 N3 P'
_chemical_formula_weight         315.39

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'
P P 0.1023 0.0942 '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 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   15.9046(10)
_cell_length_b                   11.0103(5)
_cell_length_c                   10.0953(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.701(3)
_cell_angle_gamma                90.00
_cell_volume                     1767.05(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    14773
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.157
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10149
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.28
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4040
_reflns_number_gt                3024
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_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^)+(0.1036P)^2^+3.1152P] 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     SHELXL
_refine_ls_extinction_coef       0.037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4040
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0823
_refine_ls_wR_factor_ref         0.2527
_refine_ls_wR_factor_gt          0.2321
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.170
_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 0.28814(6) -0.58726(8) 0.37145(9) 0.0294(3) Uani 1 1 d . . .
N1 N 0.1852(2) -0.2416(3) 0.5489(3) 0.0340(7) Uani 1 1 d . . .
N2 N 0.2178(2) -0.3330(3) 0.4805(3) 0.0344(7) Uani 1 1 d . . .
N3 N 0.23996(19) -0.4196(3) 0.5717(3) 0.0284(7) Uani 1 1 d . . .
C1 C 0.1866(2) -0.2677(4) 0.6775(4) 0.0322(8) Uani 1 1 d . . .
H1 H 0.1666 -0.2162 0.7451 0.039 Uiso 1 1 calc R . .
C2 C 0.2220(2) -0.3822(4) 0.6980(4) 0.0313(8) Uani 1 1 d . . .
C3 C 0.2422(3) -0.4586(4) 0.8055(4) 0.0369(9) Uani 1 1 d . . .
H3 H 0.2304 -0.4351 0.8936 0.044 Uiso 1 1 calc R . .
C4 C 0.2793(3) -0.5677(4) 0.7803(4) 0.0380(9) Uani 1 1 d . . .
H4 H 0.2944 -0.6203 0.8517 0.046 Uiso 1 1 calc R . .
C5 C 0.2955(2) -0.6032(4) 0.6482(4) 0.0345(9) Uani 1 1 d . . .
H5 H 0.3211 -0.6798 0.6337 0.041 Uiso 1 1 calc R . .
C6 C 0.2757(2) -0.5317(3) 0.5412(3) 0.0291(8) Uani 1 1 d . . .
C7 C 0.1765(2) -0.5701(3) 0.3100(4) 0.0304(8) Uani 1 1 d . . .
H7 H 0.1578 -0.4858 0.3312 0.037 Uiso 1 1 calc R . .
C8 C 0.1206(3) -0.6586(5) 0.3829(4) 0.0510(12) Uani 1 1 d . . .
H8A H 0.1400 -0.7426 0.3674 0.061 Uiso 1 1 calc R . .
H8B H 0.1253 -0.6424 0.4793 0.061 Uiso 1 1 calc R . .
C9 C 0.0290(3) -0.6467(7) 0.3364(5) 0.0684(17) Uani 1 1 d . . .
H9A H -0.0051 -0.7081 0.3823 0.082 Uiso 1 1 calc R . .
H9B H 0.0079 -0.5653 0.3607 0.082 Uiso 1 1 calc R . .
C10 C 0.0182(3) -0.6639(6) 0.1882(5) 0.0589(14) Uani 1 1 d . . .
H10A H -0.0412 -0.6495 0.1608 0.071 Uiso 1 1 calc R . .
H10B H 0.0326 -0.7486 0.1647 0.071 Uiso 1 1 calc R . .
C11 C 0.0746(3) -0.5767(5) 0.1148(4) 0.0461(11) Uani 1 1 d . . .
H11A H 0.0553 -0.4924 0.1293 0.055 Uiso 1 1 calc R . .
H11B H 0.0699 -0.5937 0.0186 0.055 Uiso 1 1 calc R . .
C12 C 0.1663(2) -0.5879(4) 0.1612(4) 0.0384(9) Uani 1 1 d . . .
H12A H 0.1877 -0.6692 0.1372 0.046 Uiso 1 1 calc R . .
H12B H 0.2002 -0.5264 0.1153 0.046 Uiso 1 1 calc R . .
C13 C 0.3440(2) -0.4614(3) 0.2895(3) 0.0299(8) Uani 1 1 d . . .
H13 H 0.3029 -0.3941 0.2716 0.036 Uiso 1 1 calc R . .
C14 C 0.4173(3) -0.4110(4) 0.3755(4) 0.0382(9) Uani 1 1 d . . .
H14A H 0.3957 -0.3814 0.4607 0.046 Uiso 1 1 calc R . .
H14B H 0.4583 -0.4767 0.3951 0.046 Uiso 1 1 calc R . .
C15 C 0.4612(3) -0.3066(5) 0.3043(5) 0.0508(12) Uani 1 1 d . . .
H15A H 0.4216 -0.2377 0.2933 0.061 Uiso 1 1 calc R . .
H15B H 0.5098 -0.2785 0.3596 0.061 Uiso 1 1 calc R . .
C16 C 0.4915(3) -0.3448(5) 0.1693(5) 0.0506(12) Uani 1 1 d . . .
H16A H 0.5370 -0.4056 0.1809 0.061 Uiso 1 1 calc R . .
H16B H 0.5149 -0.2734 0.1236 0.061 Uiso 1 1 calc R . .
C17 C 0.4202(3) -0.3988(4) 0.0845(4) 0.0429(10) Uani 1 1 d . . .
H17A H 0.4425 -0.4284 -0.0002 0.051 Uiso 1 1 calc R . .
H17B H 0.3778 -0.3352 0.0638 0.051 Uiso 1 1 calc R . .
C18 C 0.3786(3) -0.5038(4) 0.1564(4) 0.0354(9) Uani 1 1 d . . .
H18A H 0.4202 -0.5694 0.1725 0.042 Uiso 1 1 calc R . .
H18B H 0.3320 -0.5370 0.1001 0.042 Uiso 1 1 calc R . .

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 0.0340(5) 0.0279(5) 0.0261(5) -0.0012(4) -0.0008(4) 0.0015(4)
N1 0.0410(18) 0.0297(16) 0.0316(16) -0.0036(13) 0.0027(13) 0.0020(13)
N2 0.0451(19) 0.0302(16) 0.0277(16) 0.0029(13) -0.0006(13) 0.0042(14)
N3 0.0326(15) 0.0283(15) 0.0241(14) 0.0016(12) 0.0000(12) -0.0015(12)
C1 0.0350(19) 0.036(2) 0.0255(17) -0.0061(15) 0.0052(14) -0.0056(15)
C2 0.0319(18) 0.0361(19) 0.0259(18) -0.0029(15) -0.0002(14) -0.0085(15)
C3 0.043(2) 0.045(2) 0.0225(17) 0.0019(17) 0.0015(15) -0.0063(18)
C4 0.044(2) 0.039(2) 0.0303(19) 0.0081(16) -0.0043(16) -0.0057(17)
C5 0.039(2) 0.034(2) 0.0302(19) 0.0019(16) -0.0038(15) -0.0014(16)
C6 0.0320(18) 0.0278(18) 0.0273(17) 0.0015(14) -0.0013(14) -0.0025(14)
C7 0.0318(18) 0.0318(19) 0.0278(18) -0.0029(15) 0.0008(14) 0.0009(14)
C8 0.040(2) 0.076(3) 0.037(2) 0.013(2) -0.0036(18) -0.014(2)
C9 0.036(2) 0.120(5) 0.050(3) 0.014(3) 0.002(2) -0.020(3)
C10 0.040(2) 0.087(4) 0.050(3) 0.000(3) -0.008(2) -0.016(2)
C11 0.035(2) 0.069(3) 0.034(2) -0.002(2) -0.0050(16) 0.003(2)
C12 0.035(2) 0.053(2) 0.0278(19) -0.0005(18) -0.0007(15) 0.0036(18)
C13 0.0323(18) 0.0295(18) 0.0278(17) 0.0004(15) 0.0017(14) 0.0017(15)
C14 0.039(2) 0.044(2) 0.032(2) -0.0058(17) 0.0001(16) -0.0077(17)
C15 0.045(2) 0.057(3) 0.050(3) -0.011(2) 0.009(2) -0.020(2)
C16 0.045(2) 0.060(3) 0.047(3) -0.005(2) 0.012(2) -0.014(2)
C17 0.039(2) 0.053(3) 0.037(2) 0.0039(19) 0.0093(17) 0.0026(19)
C18 0.0352(19) 0.040(2) 0.0314(19) -0.0038(17) 0.0023(15) 0.0019(16)

_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 C6 1.836(4) . ?
P1 C13 1.854(4) . ?
P1 C7 1.872(4) . ?
N1 C1 1.330(5) . ?
N1 N2 1.334(4) . ?
N2 N3 1.365(4) . ?
N3 C2 1.378(5) . ?
N3 C6 1.397(5) . ?
C1 C2 1.393(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.404(5) . ?
C3 C4 1.365(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9500 . ?
C7 C12 1.519(5) . ?
C7 C8 1.523(6) . ?
C7 H7 1.0000 . ?
C8 C9 1.523(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.513(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.523(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.536(5) . ?
C13 C18 1.539(5) . ?
C13 H13 1.0000 . ?
C14 C15 1.536(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.519(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.526(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C6 P1 C13 103.54(16) . . ?
C6 P1 C7 98.54(16) . . ?
C13 P1 C7 103.81(17) . . ?
C1 N1 N2 110.2(3) . . ?
N1 N2 N3 106.0(3) . . ?
N2 N3 C2 111.0(3) . . ?
N2 N3 C6 124.6(3) . . ?
C2 N3 C6 124.4(3) . . ?
N1 C1 C2 109.7(3) . . ?
N1 C1 H1 125.2 . . ?
C2 C1 H1 125.2 . . ?
N3 C2 C1 103.1(3) . . ?
N3 C2 C3 119.1(4) . . ?
C1 C2 C3 137.7(4) . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 122.7(4) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 N3 114.9(3) . . ?
C5 C6 P1 121.2(3) . . ?
N3 C6 P1 123.8(3) . . ?
C12 C7 C8 110.4(3) . . ?
C12 C7 P1 112.8(3) . . ?
C8 C7 P1 109.7(3) . . ?
C12 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
P1 C7 H7 107.9 . . ?
C9 C8 C7 111.3(4) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 111.9(4) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11 110.6(4) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 111.8(4) . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C7 C12 C11 111.5(3) . . ?
C7 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C7 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C18 108.5(3) . . ?
C14 C13 P1 112.5(3) . . ?
C18 C13 P1 110.5(3) . . ?
C14 C13 H13 108.4 . . ?
C18 C13 H13 108.4 . . ?
P1 C13 H13 108.4 . . ?
C15 C14 C13 110.7(3) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 111.9(4) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 111.2(4) . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 110.8(4) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C13 110.9(3) . . ?
C17 C18 H18A 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 108.0 . . ?

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
C1 N1 N2 N3 0.3(4) . . . . ?
N1 N2 N3 C2 -0.6(4) . . . . ?
N1 N2 N3 C6 179.0(3) . . . . ?
N2 N1 C1 C2 0.1(4) . . . . ?
N2 N3 C2 C1 0.7(4) . . . . ?
C6 N3 C2 C1 -179.0(3) . . . . ?
N2 N3 C2 C3 -178.6(3) . . . . ?
C6 N3 C2 C3 1.8(5) . . . . ?
N1 C1 C2 N3 -0.4(4) . . . . ?
N1 C1 C2 C3 178.6(4) . . . . ?
N3 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C4 -178.8(4) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 N3 1.4(5) . . . . ?
C4 C5 C6 P1 -174.0(3) . . . . ?
N2 N3 C6 C5 178.0(3) . . . . ?
C2 N3 C6 C5 -2.4(5) . . . . ?
N2 N3 C6 P1 -6.9(5) . . . . ?
C2 N3 C6 P1 172.8(3) . . . . ?
C13 P1 C6 C5 -132.4(3) . . . . ?
C7 P1 C6 C5 121.1(3) . . . . ?
C13 P1 C6 N3 52.8(3) . . . . ?
C7 P1 C6 N3 -53.8(3) . . . . ?
C6 P1 C7 C12 169.8(3) . . . . ?
C13 P1 C7 C12 63.5(3) . . . . ?
C6 P1 C7 C8 -66.6(3) . . . . ?
C13 P1 C7 C8 -172.9(3) . . . . ?
C12 C7 C8 C9 -55.5(5) . . . . ?
P1 C7 C8 C9 179.5(4) . . . . ?
C7 C8 C9 C10 56.0(7) . . . . ?
C8 C9 C10 C11 -54.9(7) . . . . ?
C9 C10 C11 C12 54.6(6) . . . . ?
C8 C7 C12 C11 55.4(5) . . . . ?
P1 C7 C12 C11 178.5(3) . . . . ?
C10 C11 C12 C7 -55.5(5) . . . . ?
C6 P1 C13 C14 44.9(3) . . . . ?
C7 P1 C13 C14 147.4(3) . . . . ?
C6 P1 C13 C18 166.4(3) . . . . ?
C7 P1 C13 C18 -91.1(3) . . . . ?
C18 C13 C14 C15 57.7(4) . . . . ?
P1 C13 C14 C15 -179.6(3) . . . . ?
C13 C14 C15 C16 -56.1(5) . . . . ?
C14 C15 C16 C17 54.1(6) . . . . ?
C15 C16 C17 C18 -55.0(5) . . . . ?
C16 C17 C18 C13 58.5(4) . . . . ?
C14 C13 C18 C17 -59.5(4) . . . . ?
P1 C13 C18 C17 176.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.147